#------------------------------------------------------------------------------
#$Date: 2022-02-04 21:00:25 +0100 (Fri 04 de Feb de 2022) $
#$Revision: 272757 $
#$URL: svn://www.crystallography.net/cod/cif/7/15/84/7158469.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/
#
# All data on this site have been placed in the public domain by the
# contributors.
#
data_7158469
loop_
_publ_author_name
'Fedorowicz, Dominika'
'Banach, Sylwia'
'Koza, Patrycja'
'Frydrych, Rafał'
'Ślepokura, Katarzyna'
'Gregoliński, Janusz'
_publ_section_title
;
 Controlling chirality in the synthesis of 4 + 4 diastereomeric amine
 macrocycles derived from trans-1,2-diaminocyclopentane and
 2,6-diformylpyridine.
;
_journal_issue                   5
_journal_name_full               'Organic & biomolecular chemistry'
_journal_page_first              1080
_journal_page_last               1094
_journal_paper_doi               10.1039/d1ob02410h
_journal_volume                  20
_journal_year                    2022
_chemical_formula_moiety         'C48 H76 N12, 8(Cl), 11.3(H2 O)'
_chemical_formula_sum            'C48 H98.6 Cl8 N12 O11.3'
_chemical_formula_weight         1308.38
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-2014/7
_audit_update_record
;
2021-07-22 deposited with the CCDC.	2021-12-23 downloaded from the CCDC.
;
_cell_angle_alpha                105.35(2)
_cell_angle_beta                 108.36(2)
_cell_angle_gamma                93.77(2)
_cell_formula_units_Z            2
_cell_length_a                   13.082(2)
_cell_length_b                   13.444(2)
_cell_length_c                   20.564(3)
_cell_measurement_reflns_used    33203
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      42.72
_cell_measurement_theta_min      2.08
_cell_volume                     3265.9(10)
_computing_cell_refinement       'CrysAlisPro 1.171.41.80a (Rigaku OD, 2020)'
_computing_data_collection       'CrysAlisPro 1.171.41.80a (Rigaku OD, 2020)'
_computing_data_reduction        'CrysAlisPro 1.171.41.80a (Rigaku OD, 2020)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT-2014 (Sheldrick, 2015)'
_diffrn_ambient_temperature      100(2)
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            'HyPix-Arc 150'
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type
'Rigaku XtaLAB Synergy R, DW system, HyPix-Arc 150'
_diffrn_measurement_method       'omega scans'
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0303
_diffrn_reflns_av_unetI/netI     0.0205
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_l_max       25
_diffrn_reflns_limit_l_min       -25
_diffrn_reflns_number            77389
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         25.999
_diffrn_reflns_theta_min         1.638
_diffrn_source                   'Rotating-anode X-ray tube'
_diffrn_source_type              'Rigaku (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    0.407
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.87914
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.41.80a (Rigaku Oxford Diffraction, 2020)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.330
_exptl_crystal_description       plate
_exptl_crystal_F_000             1394
_exptl_crystal_size_max          0.18
_exptl_crystal_size_mid          0.10
_exptl_crystal_size_min          0.04
_refine_diff_density_max         0.800
_refine_diff_density_min         -0.505
_refine_diff_density_rms         0.079
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.020
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     854
_refine_ls_number_reflns         12837
_refine_ls_number_restraints     817
_refine_ls_restrained_S_all      1.037
_refine_ls_R_factor_all          0.0706
_refine_ls_R_factor_gt           0.0608
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0891P)²+5.3913P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1643
_refine_ls_wR_factor_ref         0.1702
_reflns_Friedel_coverage         0.000
_reflns_number_gt                10945
_reflns_number_total             12837
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d1ob02410h2.cif
_cod_data_source_block           2_l12hc
_cod_depositor_comments
'Adding full bibliography for 7158467--7158470.cif.'
_cod_original_formula_sum        'C48 H98.60 Cl8 N12 O11.30'
_cod_database_code               7158469
_shelx_shelxl_version_number     2014/7
_shelx_space_group_comment
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_shelx_estimated_absorpt_t_min   0.930
_shelx_estimated_absorpt_t_max   0.984
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Cl1 Cl 0.20708(6) 0.67853(5) 0.30141(3) 0.03190(17) Uani 1 1 d . . . . .
Cl2 Cl 0.20707(6) 0.63013(5) 0.01742(4) 0.03043(16) Uani 1 1 d . . . . .
Cl3 Cl 0.32082(5) 0.81042(6) 0.19523(3) 0.03006(17) Uani 1 1 d . . . . .
Cl4 Cl 0.37075(5) 0.80718(5) 0.48381(3) 0.02650(15) Uani 1 1 d . . . . .
Cl5 Cl 0.01539(8) 0.83117(7) -0.09131(5) 0.0536(3) Uani 1 1 d . . . . .
Cl6 Cl 0.6923(4) 0.48271(11) 0.33504(12) 0.0521(7) Uani 0.853(14) 1 d . U P A 1
Cl6X Cl 0.7379(18) 0.4855(7) 0.3463(7) 0.050(2) Uiso 0.147(14) 1 d . U P A 2
Cl7 Cl 0.7545(6) 0.9189(6) 0.2994(4) 0.0322(10) Uani 0.349(8) 1 d . U P B 1
O7W O 0.7345(9) 0.9087(10) 0.2913(6) 0.054(3) Uani 0.651(8) 1 d . U P B 2
Cl8 Cl 0.1086(3) 0.9800(3) 0.5443(2) 0.0468(9) Uani 0.504(8) 1 d . U P C 1
O8W O 0.1179(12) 0.9468(12) 0.5378(9) 0.051(3) Uani 0.343(12) 1 d . U P D 2
O8X O 0.1573(17) 0.9769(13) 0.5817(11) 0.039(3) Uiso 0.154(8) 1 d . U P E 3
Cl9 Cl 0.0335(4) 0.4393(3) 0.2866(3) 0.0471(14) Uani 0.304(8) 1 d . U P F 1
O9W O 0.0506(6) 0.4011(8) 0.3203(5) 0.051(2) Uani 0.380(12) 1 d . U P G 2
O9X O 0.019(3) 0.444(3) 0.3332(19) 0.039(3) Uiso 0.077(8) 1 d . U P H 3
O9Y O 0.0559(15) 0.4501(16) 0.3127(11) 0.039(3) Uiso 0.240(16) 1 d . U P I 4
Cl10 Cl 0.41722(10) 0.15773(8) 0.23436(5) 0.0488(4) Uani 0.844(4) 1 d . . P . .
N1 N 0.3262(2) 0.50030(17) 0.39220(12) 0.0273(5) Uani 1 1 d . U . . .
N2 N 0.2781(2) 0.46125(18) 0.24740(12) 0.0276(5) Uani 1 1 d . U . . .
H2A H 0.2480 0.5061 0.2748 0.033 Uiso 1 1 calc R U . . .
H2B H 0.2390 0.3963 0.2345 0.033 Uiso 1 1 calc R U . . .
N3 N 0.11277(19) 0.59105(17) 0.14062(12) 0.0253(5) Uani 1 1 d . U . . .
H3A H 0.1529 0.6386 0.1835 0.030 Uiso 1 1 calc R U . . .
H3B H 0.1307 0.6095 0.1056 0.030 Uiso 1 1 calc R U . . .
N4 N 0.03567(18) 0.76658(18) 0.11973(12) 0.0253(5) Uani 1 1 d . U . . .
N5 N 0.15637(19) 0.88141(17) 0.07183(13) 0.0263(5) Uani 1 1 d . U . . .
H5A H 0.1087 0.8573 0.0258 0.032 Uiso 1 1 calc R U . J 1
H5B H 0.1784 0.8253 0.0859 0.032 Uiso 1 1 calc R U . J 1
N6 N 0.3904(2) 0.8307(2) 0.06258(13) 0.0343(6) Uani 1 1 d . U . . .
H6A H 0.4400 0.8745 0.1039 0.041 Uiso 1 1 calc R U . K 1
H6B H 0.3527 0.7833 0.0746 0.041 Uiso 1 1 calc R U . K 1
N7 N 0.5173(2) 0.7079(2) 0.11868(14) 0.0380(6) Uani 1 1 d . U . . .
N9 N 0.40840(17) 0.90004(16) 0.35763(11) 0.0208(4) Uani 1 1 d . U . . .
H9A H 0.3604 0.8593 0.3145 0.025 Uiso 1 1 calc R U . L 1
H9B H 0.3923 0.8802 0.3928 0.025 Uiso 1 1 calc R U . L 1
N10 N 0.21620(18) 0.95065(17) 0.36157(12) 0.0226(4) Uani 1 1 d . U . . .
N11 N 0.10457(19) 0.82263(18) 0.40788(14) 0.0290(5) Uani 1 1 d . U . . .
H11A H 0.1199 0.8699 0.4519 0.035 Uiso 1 1 calc R U . . .
H11B H 0.1690 0.8106 0.4017 0.035 Uiso 1 1 calc R U . . .
N12 N 0.1828(2) 0.60535(18) 0.43293(13) 0.0295(5) Uani 1 1 d . U . . .
H12A H 0.1400 0.5541 0.3927 0.035 Uiso 1 1 calc R U . . .
H12B H 0.2287 0.6437 0.4201 0.035 Uiso 1 1 calc R U . . .
C1 C 0.3176(2) 0.4886(2) 0.45240(15) 0.0289(6) Uani 1 1 d . U . . .
C2 C 0.3710(3) 0.4188(2) 0.48566(16) 0.0344(7) Uani 1 1 d . U . . .
H2 H 0.3623 0.4110 0.5283 0.041 Uiso 1 1 calc R U . . .
C3 C 0.4365(3) 0.3618(2) 0.45483(17) 0.0363(7) Uani 1 1 d . U . . .
H3 H 0.4750 0.3148 0.4766 0.044 Uiso 1 1 calc R U . . .
C4 C 0.4459(3) 0.3734(2) 0.39158(16) 0.0337(7) Uani 1 1 d . U . . .
H4 H 0.4902 0.3344 0.3692 0.040 Uiso 1 1 calc R U . . .
C5 C 0.3890(2) 0.4430(2) 0.36229(15) 0.0289(6) Uani 1 1 d . U . . .
C6 C 0.3921(2) 0.4603(2) 0.29294(16) 0.0325(6) Uani 1 1 d . U . . .
H6C H 0.4387 0.5277 0.3034 0.039 Uiso 1 1 calc R U . . .
H6D H 0.4228 0.4036 0.2674 0.039 Uiso 1 1 calc R U . . .
C7 C 0.2650(3) 0.4917(2) 0.18027(15) 0.0328(6) Uani 1 1 d . U . . .
H7 H 0.3028 0.5650 0.1933 0.039 Uiso 1 1 calc R U . . .
C8 C 0.3057(3) 0.4187(3) 0.12629(18) 0.0508(9) Uani 1 1 d . U . . .
H8A H 0.3397 0.4587 0.1022 0.061 Uiso 1 1 calc R U . . .
H8B H 0.3599 0.3802 0.1505 0.061 Uiso 1 1 calc R U . . .
C9 C 0.2048(3) 0.3445(3) 0.07295(19) 0.0508(9) Uani 1 1 d . U . . .
H9C H 0.1888 0.2860 0.0909 0.061 Uiso 1 1 calc R U . . .
H9D H 0.2147 0.3156 0.0262 0.061 Uiso 1 1 calc R U . . .
C10 C 0.1127(3) 0.4090(2) 0.06508(16) 0.0404(8) Uani 1 1 d . U . . .
H10A H 0.0410 0.3641 0.0495 0.049 Uiso 1 1 calc R U . . .
H10B H 0.1113 0.4474 0.0299 0.049 Uiso 1 1 calc R U . . .
C11 C 0.1407(3) 0.4848(2) 0.14102(14) 0.0305(6) Uani 1 1 d . U . . .
H11 H 0.0994 0.4549 0.1669 0.037 Uiso 1 1 calc R U . . .
C12 C -0.0055(2) 0.5936(2) 0.12786(15) 0.0311(6) Uani 1 1 d . U . . .
H12C H -0.0266 0.5673 0.1632 0.037 Uiso 1 1 calc R U . . .
H12D H -0.0490 0.5471 0.0792 0.037 Uiso 1 1 calc R U . . .
C13 C -0.0301(2) 0.7024(2) 0.13445(15) 0.0284(6) Uani 1 1 d . U . . .
C14 C -0.1170(3) 0.7342(3) 0.15600(18) 0.0431(8) Uani 1 1 d . U . . .
H14 H -0.1612 0.6873 0.1674 0.052 Uiso 1 1 calc R U . . .
C15 C -0.1375(3) 0.8337(3) 0.1605(2) 0.0494(9) Uani 1 1 d . U . . .
H15 H -0.1979 0.8559 0.1734 0.059 Uiso 1 1 calc R U . . .
C16 C -0.0698(3) 0.9013(3) 0.14631(18) 0.0432(8) Uani 1 1 d . U . . .
H16 H -0.0820 0.9710 0.1495 0.052 Uiso 1 1 calc R U . . .
C17 C 0.0167(2) 0.8649(2) 0.12726(15) 0.0300(6) Uani 1 1 d . U . . .
C18 C 0.1002(3) 0.9384(2) 0.11901(18) 0.0345(6) Uani 1 1 d . U . . .
H18A H 0.0638 0.9909 0.0983 0.041 Uiso 1 1 calc R U . . .
H18B H 0.1547 0.9760 0.1669 0.041 Uiso 1 1 calc R U . . .
C19 C 0.2531(3) 0.9497(2) 0.07424(17) 0.0342(6) Uani 0.668(10) 1 d D U P M 1
H19 H 0.3049 0.9764 0.1249 0.041 Uiso 0.668(10) 1 calc R U P M 1
C20 C 0.2169(7) 1.0440(6) 0.0478(5) 0.0405(12) Uani 0.668(10) 1 d D U P M 1
H20A H 0.1468 1.0229 0.0070 0.049 Uiso 0.668(10) 1 calc R U P M 1
H20B H 0.2092 1.1010 0.0870 0.049 Uiso 0.668(10) 1 calc R U P M 1
C21 C 0.3091(5) 1.0772(5) 0.0247(4) 0.0474(13) Uani 0.668(10) 1 d D U P M 1
H21A H 0.2796 1.0918 -0.0218 0.057 Uiso 0.668(10) 1 calc R U P M 1
H21B H 0.3560 1.1415 0.0610 0.057 Uiso 0.668(10) 1 calc R U P M 1
C22 C 0.3737(4) 0.9896(4) 0.0176(4) 0.0441(12) Uani 0.668(10) 1 d D U P M 1
H22A H 0.4474 1.0115 0.0548 0.053 Uiso 0.668(10) 1 calc R U P M 1
H22B H 0.3820 0.9709 -0.0301 0.053 Uiso 0.668(10) 1 calc R U P M 1
C23 C 0.3126(3) 0.8927(3) 0.02671(18) 0.0381(6) Uani 0.668(10) 1 d D U P M 1
H23 H 0.2598 0.8476 -0.0206 0.046 Uiso 0.668(10) 1 calc R U P M 1
C19X C 0.2531(3) 0.9497(2) 0.07424(17) 0.0342(6) Uani 0.332(10) 1 d D U P M 2
H19X H 0.3048 0.9775 0.1249 0.041 Uiso 0.332(10) 1 calc R U P M 2
C20X C 0.2301(16) 1.0416(12) 0.0421(10) 0.0429(19) Uiso 0.332(10) 1 d D U P M 2
H20C H 0.1504 1.0380 0.0196 0.051 Uiso 0.332(10) 1 calc R U P M 2
H20D H 0.2594 1.1091 0.0805 0.051 Uiso 0.332(10) 1 calc R U P M 2
C21X C 0.2842(10) 1.0338(10) -0.0136(7) 0.048(2) Uiso 0.332(10) 1 d D U P M 2
H21C H 0.2280 1.0068 -0.0622 0.058 Uiso 0.332(10) 1 calc R U P M 2
H21D H 0.3192 1.1044 -0.0084 0.058 Uiso 0.332(10) 1 calc R U P M 2
C22X C 0.3683(8) 0.9633(9) -0.0062(8) 0.049(2) Uiso 0.332(10) 1 d D U P M 2
H22C H 0.4414 1.0009 0.0271 0.059 Uiso 0.332(10) 1 calc R U P M 2
H22D H 0.3727 0.9241 -0.0530 0.059 Uiso 0.332(10) 1 calc R U P M 2
C23X C 0.3126(3) 0.8927(3) 0.02671(18) 0.0381(6) Uani 0.332(10) 1 d D U P M 2
H23X H 0.2552 0.8404 -0.0150 0.046 Uiso 0.332(10) 1 calc R U P M 2
C24 C 0.4494(3) 0.7747(3) 0.01728(19) 0.0476(8) Uani 1 1 d . U . . .
H24A H 0.4977 0.8261 0.0089 0.057 Uiso 1 1 calc R U . . .
H24B H 0.3962 0.7324 -0.0299 0.057 Uiso 1 1 calc R U . . .
C25 C 0.5163(3) 0.7047(3) 0.05255(17) 0.0405(7) Uani 1 1 d . U . . .
C26 C 0.5718(3) 0.6387(3) 0.01776(19) 0.0490(9) Uani 1 1 d . U . . .
H26 H 0.5706 0.6386 -0.0287 0.059 Uiso 1 1 calc R U . . .
C27 C 0.6287(3) 0.5735(3) 0.0510(2) 0.0542(10) Uani 1 1 d . U . . .
H27 H 0.6670 0.5273 0.0276 0.065 Uiso 1 1 calc R U . . .
C28 C 0.6301(3) 0.5753(3) 0.11899(19) 0.0473(9) Uani 1 1 d . U . . .
H28 H 0.6689 0.5306 0.1430 0.057 Uiso 1 1 calc R U . . .
C29 C 0.5729(2) 0.6444(3) 0.15085(16) 0.0382(7) Uani 1 1 d . U . . .
C30 C 0.5679(3) 0.6498(3) 0.22438(17) 0.0419(8) Uani 1 1 d . U . . .
H30A H 0.5071 0.5970 0.2193 0.050 Uiso 1 1 calc R U . N 1
H30B H 0.6367 0.6340 0.2542 0.050 Uiso 1 1 calc R U . N 1
N8 N 0.5509(2) 0.7556(2) 0.26011(13) 0.0333(5) Uani 0.567(7) 1 d D U P O 1
H8C H 0.4982 0.7758 0.2276 0.040 Uiso 0.567(7) 1 calc R U P O 1
H8D H 0.6137 0.8011 0.2733 0.040 Uiso 0.567(7) 1 calc R U P O 1
C31 C 0.5189(5) 0.7645(3) 0.3252(2) 0.0320(12) Uani 0.567(7) 1 d D U P O 1
H31 H 0.4420 0.7280 0.3088 0.038 Uiso 0.567(7) 1 calc R U P O 1
C32 C 0.5902(5) 0.7227(4) 0.3844(3) 0.0342(12) Uani 0.567(7) 1 d D U P O 1
H32A H 0.5458 0.6937 0.4082 0.041 Uiso 0.567(7) 1 calc R U P O 1
H32B H 0.6290 0.6682 0.3647 0.041 Uiso 0.567(7) 1 calc R U P O 1
C33 C 0.6693(4) 0.8199(4) 0.4357(3) 0.0334(12) Uani 0.567(7) 1 d D U P O 1
H33A H 0.7276 0.8360 0.4171 0.040 Uiso 0.567(7) 1 calc R U P O 1
H33B H 0.7032 0.8105 0.4836 0.040 Uiso 0.567(7) 1 calc R U P O 1
C34 C 0.5996(7) 0.9074(5) 0.4401(3) 0.0271(14) Uani 0.567(7) 1 d D U P O 1
H34A H 0.6454 0.9771 0.4571 0.032 Uiso 0.567(7) 1 calc R U P O 1
H34B H 0.5582 0.9046 0.4726 0.032 Uiso 0.567(7) 1 calc R U P O 1
C35 C 0.5225(2) 0.8835(2) 0.36194(15) 0.0277(5) Uani 0.567(7) 1 d D U P O 1
H35 H 0.5513 0.9271 0.3371 0.033 Uiso 0.567(7) 1 calc R U P O 1
N8X N 0.5509(2) 0.7556(2) 0.26011(13) 0.0333(5) Uani 0.433(7) 1 d D U P O 2
H8XA H 0.4903 0.7711 0.2305 0.040 Uiso 0.433(7) 1 calc R U P O 2
H8XB H 0.6088 0.8029 0.2663 0.040 Uiso 0.433(7) 1 calc R U P O 2
C31X C 0.5380(6) 0.7679(3) 0.3316(2) 0.0379(16) Uiso 0.433(7) 1 d D U P O 2
H31X H 0.4768 0.7161 0.3284 0.046 Uiso 0.433(7) 1 calc R U P O 2
C32X C 0.6479(6) 0.7608(6) 0.3857(3) 0.0286(14) Uiso 0.433(7) 1 d D U P O 2
H32C H 0.6546 0.6874 0.3844 0.034 Uiso 0.433(7) 1 calc R U P O 2
H32D H 0.7103 0.7920 0.3762 0.034 Uiso 0.433(7) 1 calc R U P O 2
C33X C 0.6408(7) 0.8238(5) 0.4566(3) 0.0301(15) Uiso 0.433(7) 1 d D U P O 2
H33C H 0.7123 0.8395 0.4959 0.036 Uiso 0.433(7) 1 calc R U P O 2
H33D H 0.5858 0.7872 0.4698 0.036 Uiso 0.433(7) 1 calc R U P O 2
C34X C 0.6055(12) 0.9232(6) 0.4391(4) 0.0284(18) Uiso 0.433(7) 1 d D U P O 2
H34C H 0.6687 0.9707 0.4416 0.034 Uiso 0.433(7) 1 calc R U P O 2
H34D H 0.5713 0.9609 0.4729 0.034 Uiso 0.433(7) 1 calc R U P O 2
C35X C 0.5225(2) 0.8835(2) 0.36194(15) 0.0277(5) Uani 0.433(7) 1 d D U P O 2
H35X H 0.5455 0.9246 0.3335 0.033 Uiso 0.433(7) 1 calc R U P O 2
C36 C 0.3960(2) 1.01171(19) 0.36599(14) 0.0214(5) Uani 1 1 d . U . . .
H36A H 0.4187 1.0347 0.3300 0.026 Uiso 1 1 calc R U . . .
H36B H 0.4445 1.0554 0.4143 0.026 Uiso 1 1 calc R U . . .
C37 C 0.2803(2) 1.0273(2) 0.35652(13) 0.0216(5) Uani 1 1 d . U . . .
C38 C 0.2437(2) 1.1163(2) 0.34204(16) 0.0305(6) Uani 1 1 d . U . . .
H38 H 0.2915 1.1688 0.3379 0.037 Uiso 1 1 calc R U . . .
C39 C 0.1368(3) 1.1271(2) 0.33377(19) 0.0382(7) Uani 1 1 d . U . . .
H39 H 0.1102 1.1882 0.3252 0.046 Uiso 1 1 calc R U . . .
C40 C 0.0683(3) 1.0477(2) 0.33806(18) 0.0352(7) Uani 1 1 d . U . . .
H40 H -0.0059 1.0529 0.3320 0.042 Uiso 1 1 calc R U . . .
C41 C 0.1110(2) 0.9606(2) 0.35133(16) 0.0277(6) Uani 1 1 d . U . . .
C42 C 0.0417(2) 0.8673(2) 0.35184(19) 0.0339(6) Uani 1 1 d . U . . .
H42A H -0.0244 0.8885 0.3616 0.041 Uiso 1 1 calc R U . . .
H42B H 0.0182 0.8138 0.3042 0.041 Uiso 1 1 calc R U . . .
C43 C 0.0434(2) 0.7222(2) 0.40547(19) 0.0345(7) Uani 1 1 d . U . . .
H43 H 0.0235 0.6712 0.3564 0.041 Uiso 1 1 calc R U . . .
C44 C -0.0619(3) 0.7383(3) 0.4241(3) 0.0518(9) Uani 1 1 d . U . . .
H44A H -0.0668 0.8136 0.4388 0.062 Uiso 1 1 calc R U . . .
H44B H -0.1274 0.7018 0.3818 0.062 Uiso 1 1 calc R U . . .
C45 C -0.0539(4) 0.6939(3) 0.4841(3) 0.0618(10) Uani 1 1 d . U . . .
H45A H -0.1262 0.6583 0.4785 0.074 Uiso 1 1 calc R U . . .
H45B H -0.0257 0.7496 0.5309 0.074 Uiso 1 1 calc R U . . .
C46 C 0.0253(3) 0.6162(3) 0.4796(2) 0.0518(9) Uani 1 1 d . U . . .
H46A H -0.0109 0.5495 0.4414 0.062 Uiso 1 1 calc R U . . .
H46B H 0.0575 0.6018 0.5260 0.062 Uiso 1 1 calc R U . . .
C47 C 0.1116(3) 0.6746(2) 0.46102(18) 0.0343(6) Uani 1 1 d . U . . .
H47 H 0.1581 0.7319 0.5047 0.041 Uiso 1 1 calc R U . . .
C48 C 0.2487(3) 0.5560(2) 0.48521(16) 0.0339(6) Uani 1 1 d . U . . .
H48A H 0.1996 0.5129 0.4990 0.041 Uiso 1 1 calc R U . . .
H48B H 0.2962 0.6109 0.5291 0.041 Uiso 1 1 calc R U . . .
O1W O 0.6290(3) 1.1589(3) 0.35953(18) 0.0880(11) Uani 1 1 d D . . . .
H1W H 0.6643 1.2120 0.3576 0.132 Uiso 1 1 d DR U . . .
H2W H 0.6197 1.1739 0.3994 0.132 Uiso 1 1 d DR U . . .
O2W O 0.2008(3) 0.2586(2) 0.22494(15) 0.0566(11) Uani 0.875(7) 1 d D U P P 1
O2X O 0.1233(4) 0.2611(10) 0.2043(2) 0.056(4) Uiso 0.125(7) 1 d D U P P 2
H3W H 0.1618 0.2315 0.1815 0.084 Uiso 1 1 d DR U . . .
H4W H 0.1588 0.2749 0.2484 0.084 Uiso 1 1 d DR U . . .
O3W O -0.1406(4) 0.5348(5) 0.2518(2) 0.0583(16) Uani 0.736(15) 1 d . U P Q 1
O3X O -0.1648(10) 0.5828(13) 0.2663(7) 0.048(3) Uiso 0.264(15) 1 d . U P Q 2
O4W O 0.5462(4) 0.3185(4) 0.1867(3) 0.0760(15) Uani 0.678(8) 1 d . U P R 1
O4X O 0.6098(10) 0.3681(9) 0.1728(6) 0.082(3) Uiso 0.322(8) 1 d . U P R 2
O5W O 0.5503(5) 0.9725(6) 0.1881(5) 0.0647(19) Uani 0.60(2) 1 d . U P S 1
O5X O 0.6143(11) 0.9692(10) 0.1634(7) 0.046(3) Uiso 0.203(7) 1 d . U P T 2
O5Y O 0.5452(14) 0.9951(14) 0.1694(12) 0.041(3) Uiso 0.199(19) 1 d . U P U 3
O6W O -0.2043(10) 0.3791(8) 0.1364(4) 0.089(3) Uani 0.519(14) 1 d . U P V 1
O6X O -0.1356(11) 0.3636(6) 0.1370(4) 0.078(3) Uani 0.481(14) 1 d . U P V 2
O10W O 0.7836(5) 1.2858(4) 0.3568(3) 0.0568(13) Uiso 0.5 1 d . U P W 4
O11W O 0.9115(7) 1.2418(6) 0.2965(4) 0.086(2) Uiso 0.5 1 d . U P W 4
O12W O 0.8839(14) 1.3404(13) 0.3428(9) 0.095(5) Uiso 0.25 1 d . U P W 4
O13W O 0.8170(9) 1.1496(9) 0.3438(6) 0.058(3) Uiso 0.25 1 d . U P X 4
O14W O 0.952(3) 1.256(3) 0.2622(19) 0.186(12) Uiso 0.25 1 d . U P Y 5
O15W O 0.5580(18) 1.1794(16) 0.1460(11) 0.117(6) Uiso 0.25 1 d . U P Z 5
O16W O 0.6324(10) 1.1497(9) 0.1406(6) 0.056(2) Uiso 0.25 1 d . U P Z 5
O17W O 0.7099(9) 1.2331(8) 0.1469(6) 0.050(2) Uiso 0.25 1 d . U P Z 5
O18W O 0.8318(15) 1.1943(15) 0.1638(10) 0.098(4) Uiso 0.25 1 d . U P Z 5
O19W O 0.8402(12) 1.1342(12) 0.1805(8) 0.079(3) Uiso 0.25 1 d . U P Z 5
O20W O 0.7339(12) 1.0447(11) 0.1826(8) 0.067(3) Uiso 0.25 1 d . U P Z 5
O21W O 0.7688(15) 1.0883(15) 0.2097(10) 0.092(4) Uiso 0.25 1 d . U P Z 5
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C1 N1 C5 118.4(2) . . ?
C6 N2 C7 116.5(2) . . ?
C6 N2 H2A 108.2 . . ?
C7 N2 H2A 108.2 . . ?
C6 N2 H2B 108.2 . . ?
C7 N2 H2B 108.2 . . ?
H2A N2 H2B 107.3 . . ?
C12 N3 C11 111.7(2) . . ?
C12 N3 H3A 109.3 . . ?
C11 N3 H3A 109.3 . . ?
C12 N3 H3B 109.3 . . ?
C11 N3 H3B 109.3 . . ?
H3A N3 H3B 107.9 . . ?
C13 N4 C17 117.5(3) . . ?
C18 N5 C19X 111.7(2) . . ?
C18 N5 C19 111.7(2) . . ?
C18 N5 H5A 109.3 . . ?
C19 N5 H5A 109.3 . . ?
C18 N5 H5B 109.3 . . ?
C19 N5 H5B 109.3 . . ?
H5A N5 H5B 107.9 . . ?
C24 N6 C23 113.4(3) . . ?
C24 N6 C23X 113.4(3) . . ?
C24 N6 H6A 108.9 . . ?
C23 N6 H6A 108.9 . . ?
C24 N6 H6B 108.9 . . ?
C23 N6 H6B 108.9 . . ?
H6A N6 H6B 107.7 . . ?
C29 N7 C25 118.5(3) . . ?
C36 N9 C35 111.3(2) . . ?
C36 N9 C35X 111.3(2) . . ?
C36 N9 H9A 109.4 . . ?
C35 N9 H9A 109.4 . . ?
C36 N9 H9B 109.4 . . ?
C35 N9 H9B 109.4 . . ?
H9A N9 H9B 108.0 . . ?
C37 N10 C41 117.8(2) . . ?
C42 N11 C43 112.2(2) . . ?
C42 N11 H11A 109.2 . . ?
C43 N11 H11A 109.2 . . ?
C42 N11 H11B 109.2 . . ?
C43 N11 H11B 109.2 . . ?
H11A N11 H11B 107.9 . . ?
C48 N12 C47 113.8(2) . . ?
C48 N12 H12A 108.8 . . ?
C47 N12 H12A 108.8 . . ?
C48 N12 H12B 108.8 . . ?
C47 N12 H12B 108.8 . . ?
H12A N12 H12B 107.7 . . ?
N1 C1 C2 122.6(3) . . ?
N1 C1 C48 116.8(2) . . ?
C2 C1 C48 120.5(3) . . ?
C3 C2 C1 118.1(3) . . ?
C3 C2 H2 120.9 . . ?
C1 C2 H2 120.9 . . ?
C2 C3 C4 119.6(3) . . ?
C2 C3 H3 120.2 . . ?
C4 C3 H3 120.2 . . ?
C5 C4 C3 118.1(3) . . ?
C5 C4 H4 121.0 . . ?
C3 C4 H4 121.0 . . ?
N1 C5 C4 123.1(3) . . ?
N1 C5 C6 114.6(2) . . ?
C4 C5 C6 122.4(3) . . ?
N2 C6 C5 108.2(2) . . ?
N2 C6 H6C 110.1 . . ?
C5 C6 H6C 110.1 . . ?
N2 C6 H6D 110.1 . . ?
C5 C6 H6D 110.1 . . ?
H6C C6 H6D 108.4 . . ?
N2 C7 C8 114.3(3) . . ?
N2 C7 C11 107.4(2) . . ?
C8 C7 C11 105.9(3) . . ?
N2 C7 H7 109.7 . . ?
C8 C7 H7 109.7 . . ?
C11 C7 H7 109.7 . . ?
C9 C8 C7 104.7(3) . . ?
C9 C8 H8A 110.8 . . ?
C7 C8 H8A 110.8 . . ?
C9 C8 H8B 110.8 . . ?
C7 C8 H8B 110.8 . . ?
H8A C8 H8B 108.9 . . ?
C8 C9 C10 105.8(3) . . ?
C8 C9 H9C 110.6 . . ?
C10 C9 H9C 110.6 . . ?
C8 C9 H9D 110.6 . . ?
C10 C9 H9D 110.6 . . ?
H9C C9 H9D 108.7 . . ?
C9 C10 C11 103.5(3) . . ?
C9 C10 H10A 111.1 . . ?
C11 C10 H10A 111.1 . . ?
C9 C10 H10B 111.1 . . ?
C11 C10 H10B 111.1 . . ?
H10A C10 H10B 109.0 . . ?
N3 C11 C10 112.8(2) . . ?
N3 C11 C7 110.8(2) . . ?
C10 C11 C7 106.8(3) . . ?
N3 C11 H11 108.8 . . ?
C10 C11 H11 108.8 . . ?
C7 C11 H11 108.8 . . ?
N3 C12 C13 111.1(2) . . ?
N3 C12 H12C 109.4 . . ?
C13 C12 H12C 109.4 . . ?
N3 C12 H12D 109.4 . . ?
C13 C12 H12D 109.4 . . ?
H12C C12 H12D 108.0 . . ?
N4 C13 C14 122.4(3) . . ?
N4 C13 C12 116.7(3) . . ?
C14 C13 C12 121.0(3) . . ?
C15 C14 C13 119.2(3) . . ?
C15 C14 H14 120.4 . . ?
C13 C14 H14 120.4 . . ?
C14 C15 C16 119.2(3) . . ?
C14 C15 H15 120.4 . . ?
C16 C15 H15 120.4 . . ?
C15 C16 C17 118.3(3) . . ?
C15 C16 H16 120.9 . . ?
C17 C16 H16 120.9 . . ?
N4 C17 C16 123.4(3) . . ?
N4 C17 C18 116.0(2) . . ?
C16 C17 C18 120.5(3) . . ?
N5 C18 C17 111.3(2) . . ?
N5 C18 H18A 109.4 . . ?
C17 C18 H18A 109.4 . . ?
N5 C18 H18B 109.4 . . ?
C17 C18 H18B 109.4 . . ?
H18A C18 H18B 108.0 . . ?
N5 C19 C23 112.7(2) . . ?
N5 C19 C20 110.2(4) . . ?
C23 C19 C20 107.1(3) . . ?
N5 C19 H19 108.9 . . ?
C23 C19 H19 108.9 . . ?
C20 C19 H19 108.9 . . ?
C21 C20 C19 102.9(4) . . ?
C21 C20 H20A 111.2 . . ?
C19 C20 H20A 111.2 . . ?
C21 C20 H20B 111.2 . . ?
C19 C20 H20B 111.2 . . ?
H20A C20 H20B 109.1 . . ?
C22 C21 C20 107.6(4) . . ?
C22 C21 H21A 110.2 . . ?
C20 C21 H21A 110.2 . . ?
C22 C21 H21B 110.2 . . ?
C20 C21 H21B 110.2 . . ?
H21A C21 H21B 108.5 . . ?
C21 C22 C23 109.0(4) . . ?
C21 C22 H22A 109.9 . . ?
C23 C22 H22A 109.9 . . ?
C21 C22 H22B 109.9 . . ?
C23 C22 H22B 109.9 . . ?
H22A C22 H22B 108.3 . . ?
N6 C23 C19 112.5(2) . . ?
N6 C23 C22 111.9(3) . . ?
C19 C23 C22 99.0(3) . . ?
N6 C23 H23 111.0 . . ?
C19 C23 H23 111.0 . . ?
C22 C23 H23 111.0 . . ?
N5 C19X C23X 112.7(2) . . ?
N5 C19X C20X 116.9(8) . . ?
C23X C19X C20X 98.7(5) . . ?
N5 C19X H19X 109.3 . . ?
C23X C19X H19X 109.3 . . ?
C20X C19X H19X 109.3 . . ?
C21X C20X C19X 108.7(7) . . ?
C21X C20X H20C 109.9 . . ?
C19X C20X H20C 109.9 . . ?
C21X C20X H20D 109.9 . . ?
C19X C20X H20D 109.9 . . ?
H20C C20X H20D 108.3 . . ?
C22X C21X C20X 111.6(8) . . ?
C22X C21X H21C 109.3 . . ?
C20X C21X H21C 109.3 . . ?
C22X C21X H21D 109.3 . . ?
C20X C21X H21D 109.3 . . ?
H21C C21X H21D 108.0 . . ?
C21X C22X C23X 95.7(6) . . ?
C21X C22X H22C 112.6 . . ?
C23X C22X H22C 112.6 . . ?
C21X C22X H22D 112.6 . . ?
C23X C22X H22D 112.6 . . ?
H22C C22X H22D 110.1 . . ?
N6 C23X C19X 112.5(2) . . ?
N6 C23X C22X 111.5(4) . . ?
C19X C23X C22X 114.6(5) . . ?
N6 C23X H23X 105.8 . . ?
C19X C23X H23X 105.8 . . ?
C22X C23X H23X 105.8 . . ?
N6 C24 C25 110.9(3) . . ?
N6 C24 H24A 109.5 . . ?
C25 C24 H24A 109.5 . . ?
N6 C24 H24B 109.5 . . ?
C25 C24 H24B 109.5 . . ?
H24A C24 H24B 108.0 . . ?
N7 C25 C26 122.1(4) . . ?
N7 C25 C24 116.7(3) . . ?
C26 C25 C24 121.2(3) . . ?
C27 C26 C25 119.2(3) . . ?
C27 C26 H26 120.4 . . ?
C25 C26 H26 120.4 . . ?
C26 C27 C28 119.6(3) . . ?
C26 C27 H27 120.2 . . ?
C28 C27 H27 120.2 . . ?
C27 C28 C29 117.9(4) . . ?
C27 C28 H28 121.0 . . ?
C29 C28 H28 121.0 . . ?
N7 C29 C28 122.7(3) . . ?
N7 C29 C30 115.8(3) . . ?
C28 C29 C30 121.5(3) . . ?
N8X C30 C29 110.1(3) . . ?
N8 C30 C29 110.1(3) . . ?
N8 C30 H30A 109.6 . . ?
C29 C30 H30A 109.6 . . ?
N8 C30 H30B 109.6 . . ?
C29 C30 H30B 109.6 . . ?
H30A C30 H30B 108.2 . . ?
C30 N8 C31 115.2(3) . . ?
C30 N8 H8C 108.5 . . ?
C31 N8 H8C 108.5 . . ?
C30 N8 H8D 108.5 . . ?
C31 N8 H8D 108.5 . . ?
H8C N8 H8D 107.5 . . ?
N8 C31 C32 117.7(4) . . ?
N8 C31 C35 107.7(3) . . ?
C32 C31 C35 106.2(3) . . ?
N8 C31 H31 108.3 . . ?
C32 C31 H31 108.3 . . ?
C35 C31 H31 108.3 . . ?
C33 C32 C31 102.4(4) . . ?
C33 C32 H32A 111.3 . . ?
C31 C32 H32A 111.3 . . ?
C33 C32 H32B 111.3 . . ?
C31 C32 H32B 111.3 . . ?
H32A C32 H32B 109.2 . . ?
C32 C33 C34 105.0(4) . . ?
C32 C33 H33A 110.7 . . ?
C34 C33 H33A 110.7 . . ?
C32 C33 H33B 110.7 . . ?
C34 C33 H33B 110.7 . . ?
H33A C33 H33B 108.8 . . ?
C33 C34 C35 102.9(4) . . ?
C33 C34 H34A 111.2 . . ?
C35 C34 H34A 111.2 . . ?
C33 C34 H34B 111.2 . . ?
C35 C34 H34B 111.2 . . ?
H34A C34 H34B 109.1 . . ?
N9 C35 C34 111.9(4) . . ?
N9 C35 C31 107.9(3) . . ?
C34 C35 C31 105.9(3) . . ?
N9 C35 H35 110.3 . . ?
C34 C35 H35 110.3 . . ?
C31 C35 H35 110.3 . . ?
C30 N8X C31X 114.6(3) . . ?
C30 N8X H8XA 108.6 . . ?
C31X N8X H8XA 108.6 . . ?
C30 N8X H8XB 108.6 . . ?
C31X N8X H8XB 108.6 . . ?
H8XA N8X H8XB 107.6 . . ?
N8X C31X C32X 108.7(4) . . ?
N8X C31X C35X 107.9(3) . . ?
C32X C31X C35X 103.1(4) . . ?
N8X C31X H31X 112.2 . . ?
C32X C31X H31X 112.2 . . ?
C35X C31X H31X 112.2 . . ?
C33X C32X C31X 102.0(5) . . ?
C33X C32X H32C 111.4 . . ?
C31X C32X H32C 111.4 . . ?
C33X C32X H32D 111.4 . . ?
C31X C32X H32D 111.4 . . ?
H32C C32X H32D 109.2 . . ?
C32X C33X C34X 101.2(7) . . ?
C32X C33X H33C 111.5 . . ?
C34X C33X H33C 111.5 . . ?
C32X C33X H33D 111.5 . . ?
C34X C33X H33D 111.5 . . ?
H33C C33X H33D 109.4 . . ?
C33X C34X C35X 104.6(5) . . ?
C33X C34X H34C 110.8 . . ?
C35X C34X H34C 110.8 . . ?
C33X C34X H34D 110.8 . . ?
C35X C34X H34D 110.8 . . ?
H34C C34X H34D 108.9 . . ?
N9 C35X C34X 113.2(7) . . ?
N9 C35X C31X 116.2(3) . . ?
C34X C35X C31X 105.5(4) . . ?
N9 C35X H35X 107.2 . . ?
C34X C35X H35X 107.2 . . ?
C31X C35X H35X 107.2 . . ?
N9 C36 C37 111.4(2) . . ?
N9 C36 H36A 109.3 . . ?
C37 C36 H36A 109.3 . . ?
N9 C36 H36B 109.3 . . ?
C37 C36 H36B 109.3 . . ?
H36A C36 H36B 108.0 . . ?
N10 C37 C38 123.0(2) . . ?
N10 C37 C36 116.2(2) . . ?
C38 C37 C36 120.8(2) . . ?
C39 C38 C37 118.7(3) . . ?
C39 C38 H38 120.7 . . ?
C37 C38 H38 120.7 . . ?
C38 C39 C40 119.2(3) . . ?
C38 C39 H39 120.4 . . ?
C40 C39 H39 120.4 . . ?
C41 C40 C39 118.3(3) . . ?
C41 C40 H40 120.9 . . ?
C39 C40 H40 120.9 . . ?
N10 C41 C40 122.9(3) . . ?
N10 C41 C42 114.7(2) . . ?
C40 C41 C42 122.3(3) . . ?
N11 C42 C41 110.0(2) . . ?
N11 C42 H42A 109.7 . . ?
C41 C42 H42A 109.7 . . ?
N11 C42 H42B 109.7 . . ?
C41 C42 H42B 109.7 . . ?
H42A C42 H42B 108.2 . . ?
N11 C43 C47 111.5(2) . . ?
N11 C43 C44 112.5(2) . . ?
C47 C43 C44 105.0(3) . . ?
N11 C43 H43 109.3 . . ?
C47 C43 H43 109.3 . . ?
C44 C43 H43 109.3 . . ?
C45 C44 C43 106.5(3) . . ?
C45 C44 H44A 110.4 . . ?
C43 C44 H44A 110.4 . . ?
C45 C44 H44B 110.4 . . ?
C43 C44 H44B 110.4 . . ?
H44A C44 H44B 108.6 . . ?
C44 C45 C46 105.1(3) . . ?
C44 C45 H45A 110.7 . . ?
C46 C45 H45A 110.7 . . ?
C44 C45 H45B 110.7 . . ?
C46 C45 H45B 110.7 . . ?
H45A C45 H45B 108.8 . . ?
C45 C46 C47 101.9(3) . . ?
C45 C46 H46A 111.4 . . ?
C47 C46 H46A 111.4 . . ?
C45 C46 H46B 111.4 . . ?
C47 C46 H46B 111.4 . . ?
H46A C46 H46B 109.3 . . ?
N12 C47 C43 112.4(3) . . ?
N12 C47 C46 113.3(3) . . ?
C43 C47 C46 103.1(3) . . ?
N12 C47 H47 109.3 . . ?
C43 C47 H47 109.3 . . ?
C46 C47 H47 109.3 . . ?
N12 C48 C1 109.9(2) . . ?
N12 C48 H48A 109.7 . . ?
C1 C48 H48A 109.7 . . ?
N12 C48 H48B 109.7 . . ?
C1 C48 H48B 109.7 . . ?
H48A C48 H48B 108.2 . . ?
H1W O1W H2W 108.1 . . ?
H3W O2W H4W 107.7 . . ?
H3W O2X H4W 107.8 . . ?
O11W O12W O10W 98.9(10) . . ?
O15W O16W O17W 109.6(15) . . ?
O16W O17W O18W 108.1(10) . . ?
O19W O18W O17W 117.6(19) . . ?
O18W O19W O21W 126(2) . . ?
O18W O19W O20W 127.0(18) . . ?
O21W O19W O20W 21.7(8) . . ?
O21W O20W O19W 50(2) . . ?
O20W O21W O19W 109(3) . . ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
N1 C1 1.326(4) . ?
N1 C5 1.340(4) . ?
N2 C6 1.493(4) . ?
N2 C7 1.504(4) . ?
N2 H2A 0.9100 . ?
N2 H2B 0.9100 . ?
N3 C12 1.489(4) . ?
N3 C11 1.499(4) . ?
N3 H3A 0.9100 . ?
N3 H3B 0.9100 . ?
N4 C13 1.335(4) . ?
N4 C17 1.339(4) . ?
N5 C18 1.483(4) . ?
N5 C19X 1.493(4) . ?
N5 C19 1.493(4) . ?
N5 H5A 0.9100 . ?
N5 H5B 0.9100 . ?
N6 C24 1.479(4) . ?
N6 C23 1.497(4) . ?
N6 C23X 1.497(4) . ?
N6 H6A 0.9100 . ?
N6 H6B 0.9100 . ?
N7 C29 1.332(4) . ?
N7 C25 1.345(4) . ?
N9 C36 1.491(3) . ?
N9 C35 1.502(3) . ?
N9 C35X 1.502(3) . ?
N9 H9A 0.9100 . ?
N9 H9B 0.9100 . ?
N10 C37 1.331(3) . ?
N10 C41 1.346(3) . ?
N11 C42 1.483(4) . ?
N11 C43 1.504(3) . ?
N11 H11A 0.9100 . ?
N11 H11B 0.9100 . ?
N12 C48 1.486(4) . ?
N12 C47 1.495(4) . ?
N12 H12A 0.9100 . ?
N12 H12B 0.9100 . ?
C1 C2 1.401(4) . ?
C1 C48 1.502(4) . ?
C2 C3 1.376(5) . ?
C2 H2 0.9500 . ?
C3 C4 1.392(5) . ?
C3 H3 0.9500 . ?
C4 C5 1.379(4) . ?
C4 H4 0.9500 . ?
C5 C6 1.516(4) . ?
C6 H6C 0.9900 . ?
C6 H6D 0.9900 . ?
C7 C8 1.531(4) . ?
C7 C11 1.555(4) . ?
C7 H7 1.0000 . ?
C8 C9 1.509(5) . ?
C8 H8A 0.9900 . ?
C8 H8B 0.9900 . ?
C9 C10 1.523(5) . ?
C9 H9C 0.9900 . ?
C9 H9D 0.9900 . ?
C10 C11 1.536(4) . ?
C10 H10A 0.9900 . ?
C10 H10B 0.9900 . ?
C11 H11 1.0000 . ?
C12 C13 1.499(4) . ?
C12 H12C 0.9900 . ?
C12 H12D 0.9900 . ?
C13 C14 1.397(4) . ?
C14 C15 1.366(5) . ?
C14 H14 0.9500 . ?
C15 C16 1.376(5) . ?
C15 H15 0.9500 . ?
C16 C17 1.386(4) . ?
C16 H16 0.9500 . ?
C17 C18 1.504(4) . ?
C18 H18A 0.9900 . ?
C18 H18B 0.9900 . ?
C19 C23 1.520(5) . ?
C19 C20 1.553(4) . ?
C19 H19 1.0000 . ?
C20 C21 1.510(7) . ?
C20 H20A 0.9900 . ?
C20 H20B 0.9900 . ?
C21 C22 1.498(7) . ?
C21 H21A 0.9900 . ?
C21 H21B 0.9900 . ?
C22 C23 1.567(5) . ?
C22 H22A 0.9900 . ?
C22 H22B 0.9900 . ?
C23 H23 1.0000 . ?
C19X C23X 1.520(5) . ?
C19X C20X 1.553(5) . ?
C19X H19X 1.0000 . ?
C20X C21X 1.510(7) . ?
C20X H20C 0.9900 . ?
C20X H20D 0.9900 . ?
C21X C22X 1.497(7) . ?
C21X H21C 0.9900 . ?
C21X H21D 0.9900 . ?
C22X C23X 1.565(5) . ?
C22X H22C 0.9900 . ?
C22X H22D 0.9900 . ?
C23X H23X 1.0000 . ?
C24 C25 1.499(5) . ?
C24 H24A 0.9900 . ?
C24 H24B 0.9900 . ?
C25 C26 1.379(5) . ?
C26 C27 1.368(6) . ?
C26 H26 0.9500 . ?
C27 C28 1.387(6) . ?
C27 H27 0.9500 . ?
C28 C29 1.389(4) . ?
C28 H28 0.9500 . ?
C29 C30 1.517(5) . ?
C30 N8X 1.484(4) . ?
C30 N8 1.484(4) . ?
C30 H30A 0.9900 . ?
C30 H30B 0.9900 . ?
N8 C31 1.502(4) . ?
N8 H8C 0.9100 . ?
N8 H8D 0.9100 . ?
C31 C32 1.544(5) . ?
C31 C35 1.568(4) . ?
C31 H31 1.0000 . ?
C32 C33 1.515(6) . ?
C32 H32A 0.9900 . ?
C32 H32B 0.9900 . ?
C33 C34 1.536(6) . ?
C33 H33A 0.9900 . ?
C33 H33B 0.9900 . ?
C34 C35 1.539(4) . ?
C34 H34A 0.9900 . ?
C34 H34B 0.9900 . ?
C35 H35 1.0000 . ?
N8X C31X 1.500(4) . ?
N8X H8XA 0.9100 . ?
N8X H8XB 0.9100 . ?
C31X C32X 1.543(5) . ?
C31X C35X 1.566(4) . ?
C31X H31X 1.0000 . ?
C32X C33X 1.515(6) . ?
C32X H32C 0.9900 . ?
C32X H32D 0.9900 . ?
C33X C34X 1.537(6) . ?
C33X H33C 0.9900 . ?
C33X H33D 0.9900 . ?
C34X C35X 1.539(4) . ?
C34X H34C 0.9900 . ?
C34X H34D 0.9900 . ?
C35X H35X 1.0000 . ?
C36 C37 1.501(4) . ?
C36 H36A 0.9900 . ?
C36 H36B 0.9900 . ?
C37 C38 1.387(4) . ?
C38 C39 1.377(4) . ?
C38 H38 0.9500 . ?
C39 C40 1.386(5) . ?
C39 H39 0.9500 . ?
C40 C41 1.384(4) . ?
C40 H40 0.9500 . ?
C41 C42 1.503(4) . ?
C42 H42A 0.9900 . ?
C42 H42B 0.9900 . ?
C43 C47 1.526(4) . ?
C43 C44 1.555(4) . ?
C43 H43 1.0000 . ?
C44 C45 1.487(6) . ?
C44 H44A 0.9900 . ?
C44 H44B 0.9900 . ?
C45 C46 1.525(5) . ?
C45 H45A 0.9900 . ?
C45 H45B 0.9900 . ?
C46 C47 1.532(4) . ?
C46 H46A 0.9900 . ?
C46 H46B 0.9900 . ?
C47 H47 1.0000 . ?
C48 H48A 0.9900 . ?
C48 H48B 0.9900 . ?
O1W H1W 0.8405 . ?
O1W H2W 0.8401 . ?
O2W H3W 0.8410 . ?
O2W H4W 0.8417 . ?
O2X H3W 0.8409 . ?
O2X H4W 0.8406 . ?
O10W O12W 1.602(18) . ?
O11W O12W 1.550(18) . ?
O15W O16W 1.10(2) . ?
O16W O17W 1.411(15) . ?
O17W O18W 1.67(2) . ?
O18W O19W 0.958(19) . ?
O19W O21W 1.45(2) . ?
O19W O20W 1.80(2) . ?
O20W O21W 0.703(19) . ?
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
N2 H2A Cl1 0.91 2.37 3.150(2) 143.2 .
N2 H2B O2W 0.91 1.83 2.709(4) 162.4 .
N2 H2B O2X 0.91 2.10 3.003(11) 169.1 .
N3 H3A Cl1 0.91 2.20 3.003(2) 146.7 .
N3 H3B Cl2 0.91 2.39 3.287(2) 166.6 .
N5 H5A Cl5 0.91 2.25 3.139(3) 165.4 .
N5 H5B Cl2 0.91 2.74 3.445(2) 134.9 .
N5 H5B Cl3 0.91 2.49 3.177(2) 132.3 .
N6 H6A O5W 0.91 1.95 2.854(6) 175.9 .
N6 H6B Cl2 0.91 2.46 3.210(3) 140.1 .
N8 H8C Cl3 0.91 2.32 3.109(3) 145.2 .
N8 H8D Cl7 0.91 2.18 3.082(8) 174.5 .
N8X H8XA Cl3 0.91 2.25 3.109(3) 157.1 .
N8X H8XB O7W 0.91 1.94 2.846(12) 173.3 .
N6 H6B Cl3 0.91 2.58 3.205(3) 126.4 .
N9 H9A Cl3 0.91 2.24 3.032(2) 145.4 .
N9 H9B Cl4 0.91 2.41 3.312(2) 170.3 .
N11 H11A Cl8 0.91 2.13 3.016(5) 164.2 .
N11 H11A O8W 0.91 1.80 2.695(16) 165.4 .
N11 H11A O8X 0.91 2.55 3.45(2) 170.8 .
N11 H11B Cl1 0.91 2.55 3.208(3) 130.1 .
N11 H11B Cl4 0.91 2.66 3.383(3) 137.3 .
N12 H12A Cl9 0.91 2.26 3.166(6) 174.1 .
N12 H12A O9W 0.91 2.19 3.063(8) 161.4 .
N12 H12A O9X 0.91 1.93 2.79(3) 157.2 .
N12 H12A O9Y 0.91 1.82 2.73(2) 179.0 .
N12 H12B Cl1 0.91 2.54 3.208(2) 130.9 .
N12 H12B Cl4 0.91 2.53 3.241(3) 135.2 .
C3 H3 Cl4 0.95 2.74 3.658(3) 161.5 2_666
C8 H8B O4W 0.99 2.58 3.499(6) 155.1 .
C10 H10B Cl2 0.99 2.79 3.626(3) 142.1 .
C11 H11 Cl9 1.00 2.90 3.847(6) 157.4 .
C12 H12D Cl2 0.99 2.86 3.764(3) 152.8 2_565
C16 H16 O19W 0.95 2.49 3.395(16) 158.5 1_455
C18 H18A Cl5 0.99 2.69 3.635(3) 159.9 2_575
C19 H19 Cl10 1.00 2.78 3.627(4) 143.3 1_565
C19X H19X Cl10 1.00 2.77 3.627(4) 144.4 1_565
C20 H20A Cl5 0.99 2.86 3.639(11) 136.6 .
C24 H24B O17W 0.99 2.55 3.332(11) 135.9 2_675
C28 H28 O3X 0.95 2.65 3.326(12) 128.4 1_655
C28 H28 O4X 0.95 2.56 3.282(13) 133.5 .
C30 H30B Cl6 0.99 2.94 3.705(4) 134.8 .
C32 H32B Cl6 0.99 2.66 3.593(5) 157.7 .
C34 H34A Cl4 0.99 2.88 3.683(6) 138.5 2_676
C34 H34B Cl4 0.99 2.81 3.659(12) 144.8 .
C36 H36A Cl10 0.99 2.88 3.804(3) 155.4 1_565
C36 H36B Cl4 0.99 2.80 3.726(3) 156.7 2_676
C42 H42A Cl7 0.99 2.88 3.735(7) 145.6 1_455
C42 H42A Cl8 0.99 2.81 3.674(5) 146.7 2_576
C43 H43 O3X 1.00 2.55 3.271(12) 129.1 .
C44 H44A Cl8 0.99 2.93 3.600(5) 125.7 .
C44 H44A Cl8 0.99 2.82 3.794(5) 169.7 2_576
C44 H44B O3X 0.99 2.37 3.162(15) 136.8 .
C46 H46A O9X 0.99 2.47 3.25(4) 136.0 .
C46 H46B O12W 0.99 2.45 3.337(18) 149.6 2_676
O1W H1W O10W 0.84 1.80 2.582(7) 154.0 .
O1W H2W Cl4 0.84 2.31 3.131(3) 165.9 2_676
O2W H3W Cl5 0.84 2.39 3.147(3) 149.5 2_565
O2W H4W Cl9 0.84 2.92 3.621(6) 141.4 .
loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C5 N1 C1 C2 -0.2(4) . . . . ?
C5 N1 C1 C48 178.6(3) . . . . ?
N1 C1 C2 C3 1.2(4) . . . . ?
C48 C1 C2 C3 -177.5(3) . . . . ?
C1 C2 C3 C4 -1.3(4) . . . . ?
C2 C3 C4 C5 0.5(4) . . . . ?
C1 N1 C5 C4 -0.7(4) . . . . ?
C1 N1 C5 C6 178.9(3) . . . . ?
C3 C4 C5 N1 0.6(4) . . . . ?
C3 C4 C5 C6 -179.0(3) . . . . ?
C7 N2 C6 C5 172.1(2) . . . . ?
N1 C5 C6 N2 -44.7(3) . . . . ?
C4 C5 C6 N2 134.9(3) . . . . ?
C6 N2 C7 C8 61.6(4) . . . . ?
C6 N2 C7 C11 178.8(2) . . . . ?
N2 C7 C8 C9 96.9(3) . . . . ?
C11 C7 C8 C9 -21.2(4) . . . . ?
C7 C8 C9 C10 35.6(4) . . . . ?
C8 C9 C10 C11 -35.6(4) . . . . ?
C12 N3 C11 C10 80.7(3) . . . . ?
C12 N3 C11 C7 -159.7(2) . . . . ?
C9 C10 C11 N3 143.7(3) . . . . ?
C9 C10 C11 C7 21.8(3) . . . . ?
N2 C7 C11 N3 113.7(2) . . . . ?
C8 C7 C11 N3 -123.7(3) . . . . ?
N2 C7 C11 C10 -123.1(2) . . . . ?
C8 C7 C11 C10 -0.6(3) . . . . ?
C11 N3 C12 C13 174.7(2) . . . . ?
C17 N4 C13 C14 0.9(4) . . . . ?
C17 N4 C13 C12 -178.2(2) . . . . ?
N3 C12 C13 N4 27.5(3) . . . . ?
N3 C12 C13 C14 -151.6(3) . . . . ?
N4 C13 C14 C15 1.7(5) . . . . ?
C12 C13 C14 C15 -179.2(3) . . . . ?
C13 C14 C15 C16 -2.3(5) . . . . ?
C14 C15 C16 C17 0.5(5) . . . . ?
C13 N4 C17 C16 -2.9(4) . . . . ?
C13 N4 C17 C18 172.8(2) . . . . ?
C15 C16 C17 N4 2.2(5) . . . . ?
C15 C16 C17 C18 -173.3(3) . . . . ?
C19X N5 C18 C17 -169.2(2) . . . . ?
C19 N5 C18 C17 -169.2(2) . . . . ?
N4 C17 C18 N5 27.2(4) . . . . ?
C16 C17 C18 N5 -157.0(3) . . . . ?
C18 N5 C19 C23 179.6(2) . . . . ?
C18 N5 C19 C20 -60.9(5) . . . . ?
N5 C19 C20 C21 -157.6(5) . . . . ?
C23 C19 C20 C21 -34.7(7) . . . . ?
C19 C20 C21 C22 15.9(8) . . . . ?
C20 C21 C22 C23 7.4(7) . . . . ?
C24 N6 C23 C19 -179.9(3) . . . . ?
C24 N6 C23 C22 -69.5(4) . . . . ?
N5 C19 C23 N6 -82.7(3) . . . . ?
C20 C19 C23 N6 156.0(5) . . . . ?
N5 C19 C23 C22 159.0(3) . . . . ?
C20 C19 C23 C22 37.6(5) . . . . ?
C21 C22 C23 N6 -146.4(4) . . . . ?
C21 C22 C23 C19 -27.6(5) . . . . ?
C18 N5 C19X C23X 179.6(2) . . . . ?
C18 N5 C19X C20X -67.1(8) . . . . ?
N5 C19X C20X C21X -125.5(12) . . . . ?
C23X C19X C20X C21X -4.5(16) . . . . ?
C19X C20X C21X C22X -17(2) . . . . ?
C20X C21X C22X C23X 28.4(15) . . . . ?
C24 N6 C23X C19X -179.9(3) . . . . ?
C24 N6 C23X C22X -49.6(7) . . . . ?
N5 C19X C23X N6 -82.7(3) . . . . ?
C20X C19X C23X N6 153.2(9) . . . . ?
N5 C19X C23X C22X 148.5(6) . . . . ?
C20X C19X C23X C22X 24.5(11) . . . . ?
C21X C22X C23X N6 -162.7(7) . . . . ?
C21X C22X C23X C19X -33.4(10) . . . . ?
C23 N6 C24 C25 -173.6(3) . . . . ?
C23X N6 C24 C25 -173.6(3) . . . . ?
C29 N7 C25 C26 -0.7(5) . . . . ?
C29 N7 C25 C24 177.9(3) . . . . ?
N6 C24 C25 N7 -3.6(4) . . . . ?
N6 C24 C25 C26 175.1(3) . . . . ?
N7 C25 C26 C27 0.8(5) . . . . ?
C24 C25 C26 C27 -177.7(3) . . . . ?
C25 C26 C27 C28 -0.4(6) . . . . ?
C26 C27 C28 C29 -0.1(6) . . . . ?
C25 N7 C29 C28 0.2(5) . . . . ?
C25 N7 C29 C30 -178.2(3) . . . . ?
C27 C28 C29 N7 0.2(5) . . . . ?
C27 C28 C29 C30 178.6(3) . . . . ?
N7 C29 C30 N8X -28.4(4) . . . . ?
C28 C29 C30 N8X 153.2(3) . . . . ?
N7 C29 C30 N8 -28.4(4) . . . . ?
C28 C29 C30 N8 153.2(3) . . . . ?
C29 C30 N8 C31 166.5(3) . . . . ?
C30 N8 C31 C32 51.6(5) . . . . ?
C30 N8 C31 C35 171.4(3) . . . . ?
N8 C31 C32 C33 94.1(5) . . . . ?
C35 C31 C32 C33 -26.5(5) . . . . ?
C31 C32 C33 C34 41.3(7) . . . . ?
C32 C33 C34 C35 -40.0(8) . . . . ?
C36 N9 C35 C34 84.7(4) . . . . ?
C36 N9 C35 C31 -159.2(2) . . . . ?
C33 C34 C35 N9 139.6(5) . . . . ?
C33 C34 C35 C31 22.2(8) . . . . ?
N8 C31 C35 N9 115.6(3) . . . . ?
C32 C31 C35 N9 -117.6(4) . . . . ?
N8 C31 C35 C34 -124.4(6) . . . . ?
C32 C31 C35 C34 2.5(6) . . . . ?
C29 C30 N8X C31X 176.5(4) . . . . ?
C30 N8X C31X C32X 68.1(5) . . . . ?
C30 N8X C31X C35X 179.3(3) . . . . ?
N8X C31X C32X C33X 153.6(5) . . . . ?
C35X C31X C32X C33X 39.3(6) . . . . ?
C31X C32X C33X C34X -48.9(9) . . . . ?
C32X C33X C34X C35X 39.6(12) . . . . ?
C36 N9 C35X C34X 75.5(6) . . . . ?
C36 N9 C35X C31X -162.3(2) . . . . ?
C33X C34X C35X N9 112.9(9) . . . . ?
C33X C34X C35X C31X -15.1(13) . . . . ?
N8X C31X C35X N9 104.3(4) . . . . ?
C32X C31X C35X N9 -140.8(4) . . . . ?
N8X C31X C35X C34X -129.4(8) . . . . ?
C32X C31X C35X C34X -14.6(9) . . . . ?
C35 N9 C36 C37 176.0(2) . . . . ?
C35X N9 C36 C37 176.0(2) . . . . ?
C41 N10 C37 C38 0.7(4) . . . . ?
C41 N10 C37 C36 -178.1(2) . . . . ?
N9 C36 C37 N10 17.1(3) . . . . ?
N9 C36 C37 C38 -161.8(2) . . . . ?
N10 C37 C38 C39 1.2(4) . . . . ?
C36 C37 C38 C39 180.0(3) . . . . ?
C37 C38 C39 C40 -1.9(5) . . . . ?
C38 C39 C40 C41 0.7(5) . . . . ?
C37 N10 C41 C40 -2.0(4) . . . . ?
C37 N10 C41 C42 175.2(3) . . . . ?
C39 C40 C41 N10 1.3(5) . . . . ?
C39 C40 C41 C42 -175.7(3) . . . . ?
C43 N11 C42 C41 -173.8(2) . . . . ?
N10 C41 C42 N11 39.1(4) . . . . ?
C40 C41 C42 N11 -143.7(3) . . . . ?
C42 N11 C43 C47 177.2(2) . . . . ?
C42 N11 C43 C44 -65.2(4) . . . . ?
N11 C43 C44 C45 -125.2(3) . . . . ?
C47 C43 C44 C45 -3.8(4) . . . . ?
C43 C44 C45 C46 -22.5(4) . . . . ?
C44 C45 C46 C47 40.0(4) . . . . ?
C48 N12 C47 C43 -178.9(2) . . . . ?
C48 N12 C47 C46 -62.4(4) . . . . ?
N11 C43 C47 N12 -87.3(3) . . . . ?
C44 C43 C47 N12 150.6(3) . . . . ?
N11 C43 C47 C46 150.3(3) . . . . ?
C44 C43 C47 C46 28.3(3) . . . . ?
C45 C46 C47 N12 -163.6(3) . . . . ?
C45 C46 C47 C43 -41.9(4) . . . . ?
C47 N12 C48 C1 -179.8(2) . . . . ?
N1 C1 C48 N12 13.3(4) . . . . ?
C2 C1 C48 N12 -167.9(3) . . . . ?
O15W O16W O17W O18W 162.7(15) . . . . ?
O16W O17W O18W O19W -17(2) . . . . ?
O17W O18W O19W O21W -17(3) . . . . ?
O17W O18W O19W O20W 11(3) . . . . ?
O18W O19W O20W O21W -97(3) . . . . ?
O18W O19W O21W O20W 100(3) . . . . ?
