#------------------------------------------------------------------------------
#$Date: 2025-08-06 00:07:45 +0200 (Wed 06 de Aug de 2025) $
#$Revision: 301600 $
#$URL: svn://www.crystallography.net/cod/cif/7/71/90/7719065.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_7719065
loop_
_publ_author_name
'Akine, Shigehisa'
'Nakano, Masato'
'Sakata, Yoko'
'Tsuzuki, Seiji'
_publ_section_title
;
 Synthesis of a xanthene-based macrocyclic imine ligand and two-step
 planarization by metalation with Ni²⁺ and Na<sup/>.
;
_journal_issue                   30
_journal_name_full
'Dalton transactions (Cambridge, England : 2003)'
_journal_page_first              11573
_journal_page_last               11580
_journal_paper_doi               10.1039/d5dt01183c
_journal_volume                  54
_journal_year                    2025
_chemical_formula_moiety         C51.50H44Cl1.50N6.50O6
_chemical_formula_sum            'C51.5 H44 Cl1.5 N6.5 O6'
_chemical_formula_weight         903.10
_chemical_name_common            C46H36N4O6(CHCl3)0.5(MeCN)2.5
_space_group_crystal_system      monoclinic
_space_group_IT_number           11
_space_group_name_Hall           '-P 2yb'
_space_group_name_H-M_alt        'P 1 21/m 1'
_atom_sites_solution_hydrogens   geom
_audit_creation_method           SHELXL-2014/7
_audit_update_record
;
2025-05-05 deposited with the CCDC.	2025-07-07 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 99.151(4)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   10.9940(14)
_cell_length_b                   23.218(3)
_cell_length_c                   17.421(3)
_cell_measurement_reflns_used    17320
_cell_measurement_temperature    93
_cell_measurement_theta_max      24.998
_cell_measurement_theta_min      3.286
_cell_volume                     4390.3(11)
_computing_cell_refinement       'CrystalClear (Rigaku/MSC Inc., 2006)'
_computing_data_collection       'CrystalClear (Rigaku/MSC Inc., 2006)'
_computing_data_reduction        'CrystalClear (Rigaku/MSC Inc., 2006)'
_computing_molecular_graphics    ORTEP-3
_computing_publication_material  ORTEP-3
_computing_structure_refinement  'SHELXL-2014 (Sheldrick, 2014)'
_computing_structure_solution    SIR97
_diffrn_ambient_temperature      93
_diffrn_detector_area_resol_mean 14.4613
_diffrn_measured_fraction_theta_full 0.994
_diffrn_measured_fraction_theta_max 0.994
_diffrn_measurement_device_type  'Rigaku Mercury (2x2 bin mode)'
_diffrn_measurement_method       dtprofit.ref
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0460
_diffrn_reflns_av_unetI/netI     0.0414
_diffrn_reflns_Laue_measured_fraction_full 0.994
_diffrn_reflns_Laue_measured_fraction_max 0.994
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       27
_diffrn_reflns_limit_k_min       -27
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            41360
_diffrn_reflns_point_group_measured_fraction_full 0.994
_diffrn_reflns_point_group_measured_fraction_max 0.994
_diffrn_reflns_theta_full        24.998
_diffrn_reflns_theta_max         24.998
_diffrn_reflns_theta_min         3.286
_exptl_absorpt_coefficient_mu    0.178
_exptl_absorpt_correction_T_max  1.0000
_exptl_absorpt_correction_T_min  0.7339
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'CrystalClear (Rigaku/MSC Inc., 2006)'
_exptl_crystal_colour            orange
_exptl_crystal_density_diffrn    1.366
_exptl_crystal_description       prismatic
_exptl_crystal_F_000             1888
_exptl_crystal_recrystallization_method
'Re-crystallisation from solvent: CHCl3/MeCN'
_exptl_crystal_size_max          0.700
_exptl_crystal_size_mid          0.200
_exptl_crystal_size_min          0.200
_refine_diff_density_max         0.511
_refine_diff_density_min         -0.841
_refine_diff_density_rms         0.066
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.078
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     660
_refine_ls_number_reflns         7892
_refine_ls_number_restraints     53
_refine_ls_restrained_S_all      1.078
_refine_ls_R_factor_all          0.0749
_refine_ls_R_factor_gt           0.0647
_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)+(0.0915P)²+4.5007P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1650
_refine_ls_wR_factor_ref         0.1804
_reflns_Friedel_coverage         0.000
_reflns_number_gt                6616
_reflns_number_total             7892
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d5dt01183c2.cif
_cod_data_source_block           nak001
_cod_depositor_comments
'Adding full bibliography for 7719065--7719067.cif.'
_cod_original_cell_volume        4390.2(10)
_cod_original_sg_symbol_H-M      'P 21/m'
_cod_original_formula_sum        'C51.50 H44 Cl1.50 N6.50 O6'
_cod_database_code               7719065
_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   0.885
_shelx_estimated_absorpt_t_max   0.965
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z'
'-x, -y, -z'
'x, -y-1/2, 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
C1 C 0.0666(2) 0.40843(10) 0.36952(13) 0.0239(5) Uani 1 1 d . . . . .
C2 C -0.0079(2) 0.37518(10) 0.31350(13) 0.0241(5) Uani 1 1 d . . . . .
C3 C -0.0117(2) 0.38929(10) 0.23469(13) 0.0247(5) Uani 1 1 d . . . . .
C4 C 0.0597(2) 0.43488(10) 0.21496(13) 0.0262(5) Uani 1 1 d . . . . .
H1 H 0.0571 0.4445 0.1617 0.031 Uiso 1 1 calc R U . . .
C5 C 0.1340(2) 0.46633(10) 0.27072(13) 0.0263(5) Uani 1 1 d . . . . .
H2 H 0.1830 0.4967 0.2556 0.032 Uiso 1 1 calc R U . . .
C6 C 0.1378(2) 0.45385(9) 0.34972(13) 0.0242(5) Uani 1 1 d . . . . .
C7 C 0.2112(2) 0.48990(10) 0.41435(13) 0.0260(5) Uani 1 1 d . . . . .
C8 C 0.2481(2) 0.45079(10) 0.48476(13) 0.0250(5) Uani 1 1 d . . . . .
C9 C 0.3536(2) 0.46020(10) 0.53988(14) 0.0273(5) Uani 1 1 d . . . . .
H3 H 0.4089 0.4902 0.5317 0.033 Uiso 1 1 calc R U . . .
C10 C 0.3784(2) 0.42660(10) 0.60584(14) 0.0272(5) Uani 1 1 d . . . . .
H4 H 0.4504 0.4338 0.6425 0.033 Uiso 1 1 calc R U . . .
C11 C 0.2985(2) 0.38197(10) 0.61925(13) 0.0252(5) Uani 1 1 d . . . . .
C12 C 0.1932(2) 0.37108(10) 0.56427(13) 0.0248(5) Uani 1 1 d . . . . .
C13 C 0.1711(2) 0.40569(10) 0.49771(13) 0.0245(5) Uani 1 1 d . . . . .
O1 O 0.06494(14) 0.39238(7) 0.44605(9) 0.0259(4) Uani 1 1 d . . . . .
O2 O -0.07241(15) 0.33074(7) 0.33684(9) 0.0273(4) Uani 1 1 d . . . . .
H5 H -0.1082 0.3129 0.2977 0.041 Uiso 1 1 calc R U . . .
C14 C -0.0836(2) 0.35576(10) 0.17365(14) 0.0278(5) Uani 1 1 d . . . . .
H6 H -0.0875 0.3682 0.1214 0.033 Uiso 1 1 calc R U . . .
N1 N -0.14246(18) 0.30981(8) 0.18689(11) 0.0258(4) Uani 1 1 d . . . . .
C15 C -0.2091(2) 0.28017(11) 0.12219(13) 0.0267(5) Uani 1 1 d . . . . .
C16 C -0.2740(2) 0.30975(11) 0.05851(14) 0.0307(5) Uani 1 1 d . . . . .
H7 H -0.2753 0.3507 0.0584 0.037 Uiso 1 1 calc R U . . .
C17 C -0.3362(2) 0.27968(12) -0.00416(14) 0.0342(6) Uani 1 1 d . . . . .
H8 H -0.3792 0.3000 -0.0475 0.041 Uiso 1 1 calc R U . . .
O3 O 0.11189(16) 0.32948(7) 0.57362(9) 0.0304(4) Uani 1 1 d . . . . .
H9 H 0.1359 0.3117 0.6153 0.046 Uiso 1 1 calc R U . . .
C18 C 0.3232(2) 0.34922(10) 0.69124(13) 0.0252(5) Uani 1 1 d . . . . .
H10 H 0.3944 0.3578 0.7279 0.030 Uiso 1 1 calc R U . . .
N2 N 0.25041(18) 0.30884(8) 0.70611(11) 0.0258(4) Uani 1 1 d . . . . .
C19 C 0.2760(2) 0.28012(10) 0.77868(13) 0.0241(5) Uani 1 1 d . . . . .
C20 C 0.3004(2) 0.30979(11) 0.84918(13) 0.0280(5) Uani 1 1 d . . . . .
H11 H 0.3005 0.3507 0.8495 0.034 Uiso 1 1 calc R U . . .
C21 C 0.3245(2) 0.27981(11) 0.91873(14) 0.0299(5) Uani 1 1 d . . . . .
H12 H 0.3411 0.3002 0.9665 0.036 Uiso 1 1 calc R U . . .
C22 C 0.3224(2) 0.51826(11) 0.38846(14) 0.0332(6) Uani 1 1 d . . . . .
H13 H 0.3781 0.4885 0.3743 0.050 Uiso 1 1 calc R U . . .
H14 H 0.3658 0.5417 0.4310 0.050 Uiso 1 1 calc R U . . .
H15 H 0.2952 0.5429 0.3433 0.050 Uiso 1 1 calc R U . . .
C23 C 0.1256(2) 0.53752(11) 0.43808(14) 0.0324(6) Uani 1 1 d . . . . .
H16 H 0.1687 0.5587 0.4830 0.049 Uiso 1 1 calc R U . . .
H17 H 0.0510 0.5198 0.4518 0.049 Uiso 1 1 calc R U . . .
H18 H 0.1029 0.5641 0.3945 0.049 Uiso 1 1 calc R U . . .
C24 C 0.8136(2) 0.57770(10) -0.00429(13) 0.0250(5) Uani 1 1 d . . . . .
C25 C 0.7355(2) 0.58302(10) -0.07554(14) 0.0265(5) Uani 1 1 d . . . . .
C26 C 0.7480(2) 0.63148(10) -0.12129(14) 0.0284(5) Uani 1 1 d . . . . .
C27 C 0.8371(2) 0.67265(11) -0.09448(15) 0.0344(6) Uani 1 1 d . . . . .
H19 H 0.8457 0.7055 -0.1257 0.041 Uiso 1 1 calc R U . . .
C28 C 0.9122(2) 0.66686(11) -0.02439(15) 0.0322(6) Uani 1 1 d . . . . .
H20 H 0.9711 0.6959 -0.0072 0.039 Uiso 1 1 calc R U . . .
C29 C 0.9030(2) 0.61849(10) 0.02211(14) 0.0260(5) Uani 1 1 d . . . . .
C30 C 0.9898(2) 0.60680(11) 0.09765(14) 0.0287(5) Uani 1 1 d . . . . .
C31 C 0.9180(2) 0.57413(10) 0.15107(14) 0.0259(5) Uani 1 1 d . . . . .
C32 C 0.9399(2) 0.57938(10) 0.23195(14) 0.0273(5) Uani 1 1 d . . . . .
H21 H 0.9974 0.6071 0.2559 0.033 Uiso 1 1 calc R U . . .
C33 C 0.8787(2) 0.54467(10) 0.27715(13) 0.0274(5) Uani 1 1 d . . . . .
H22 H 0.8941 0.5492 0.3320 0.033 Uiso 1 1 calc R U . . .
C34 C 0.7942(2) 0.50283(10) 0.24443(13) 0.0259(5) Uani 1 1 d . . . . .
C35 C 0.7688(2) 0.49812(10) 0.16290(13) 0.0250(5) Uani 1 1 d . . . . .
C36 C 0.8300(2) 0.53450(10) 0.11834(13) 0.0239(5) Uani 1 1 d . . . . .
O4 O 0.79734(15) 0.52862(7) 0.03837(9) 0.0267(4) Uani 1 1 d . . . . .
O5 O 0.65220(16) 0.54130(7) -0.09783(9) 0.0305(4) Uani 1 1 d . . . . .
H23 H 0.6114 0.5497 -0.1413 0.046 Uiso 1 1 calc R U . . .
C37 C 0.6737(2) 0.63919(11) -0.19668(14) 0.0297(5) Uani 1 1 d . . . . .
H24 H 0.6848 0.6733 -0.2249 0.036 Uiso 1 1 calc R U . . .
N3 N 0.59341(18) 0.60235(9) -0.22775(12) 0.0282(4) Uani 1 1 d . . . . .
C38 C 0.5309(2) 0.61533(10) -0.30351(14) 0.0290(5) Uani 1 1 d . . . . .
C39 C 0.5915(2) 0.64037(11) -0.35992(15) 0.0317(5) Uani 1 1 d . . . . .
H25 H 0.6774 0.6479 -0.3483 0.038 Uiso 1 1 calc R U . . .
C40 C 0.5276(2) 0.65436(11) -0.43253(14) 0.0326(6) Uani 1 1 d . . . . .
H26 H 0.5699 0.6706 -0.4708 0.039 Uiso 1 1 calc R U . . .
O6 O 0.68715(15) 0.45898(7) 0.12717(9) 0.0285(4) Uani 1 1 d . . . . .
H27 H 0.6500 0.4433 0.1602 0.043 Uiso 1 1 calc R U . . .
C41 C 0.7326(2) 0.46730(10) 0.29423(13) 0.0266(5) Uani 1 1 d . . . . .
H28 H 0.7522 0.4724 0.3489 0.032 Uiso 1 1 calc R U . . .
N4 N 0.65224(18) 0.42898(9) 0.26784(11) 0.0277(4) Uani 1 1 d . . . . .
C42 C 0.5946(2) 0.39862(10) 0.32283(13) 0.0267(5) Uani 1 1 d . . . . .
C43 C 0.6587(2) 0.38164(11) 0.39509(14) 0.0296(5) Uani 1 1 d . . . . .
H29 H 0.7449 0.3882 0.4070 0.035 Uiso 1 1 calc R U . . .
C44 C 0.5981(3) 0.35534(11) 0.44941(14) 0.0333(6) Uani 1 1 d . . . . .
H30 H 0.6426 0.3439 0.4983 0.040 Uiso 1 1 calc R U . . .
C45 C 1.0471(3) 0.66236(12) 0.13500(16) 0.0401(6) Uani 1 1 d . . . . .
H31 H 0.9816 0.6881 0.1463 0.060 Uiso 1 1 calc R U . . .
H32 H 1.0943 0.6815 0.0991 0.060 Uiso 1 1 calc R U . . .
H33 H 1.1020 0.6530 0.1834 0.060 Uiso 1 1 calc R U . . .
C46 C 1.0939(2) 0.56734(12) 0.07824(16) 0.0353(6) Uani 1 1 d . . . . .
H34 H 1.1509 0.5585 0.1260 0.053 Uiso 1 1 calc R U . . .
H35 H 1.1387 0.5870 0.0415 0.053 Uiso 1 1 calc R U . . .
H36 H 1.0584 0.5315 0.0549 0.053 Uiso 1 1 calc R U . . .
Cl1 Cl 0.6940(3) 0.32943(9) 0.67695(11) 0.0856(7) Uani 0.5 1 d D . P A -1
Cl2 Cl 0.53824(18) 0.2411(3) 0.61930(10) 0.1008(18) Uani 0.5 1 d D . P A -1
Cl3 Cl 0.59432(14) 0.2500 0.78433(8) 0.0806(5) Uani 1 2 d DS T P . .
N5 N 0.1636(3) 0.2500 0.27202(19) 0.0388(7) Uani 1 2 d S T P . .
C47 C 0.6510(6) 0.2585(7) 0.6969(3) 0.062(3) Uani 0.5 1 d D . P A -1
H37 H 0.7232 0.2324 0.6968 0.074 Uiso 0.5 1 calc R U P A -1
C48 C 0.1653(3) 0.2500 0.3376(2) 0.0303(8) Uani 1 2 d S T P . .
C49 C 0.1674(3) 0.2500 0.4212(2) 0.0341(8) Uani 1 2 d S T P . .
H38 H 0.2530 0.2500 0.4477 0.051 Uiso 1 2 calc DR U P . .
H39 H 0.1253 0.2155 0.4361 0.051 Uiso 0.5 1 calc R U P . .
H40 H 0.1253 0.2845 0.4361 0.051 Uiso 0.5 1 calc R U P . .
N6 N 0.5606(4) 0.4232(2) -0.19503(19) 0.0953(14) Uani 1 1 d . . . . .
C50 C 0.5436(3) 0.42603(14) -0.13256(19) 0.0517(8) Uani 1 1 d . . . . .
C51 C 0.5209(3) 0.43012(12) -0.05340(16) 0.0389(6) Uani 1 1 d . . . . .
H41 H 0.4541 0.4577 -0.0507 0.058 Uiso 1 1 calc R U . . .
H42 H 0.5958 0.4433 -0.0199 0.058 Uiso 1 1 calc R U . . .
H43 H 0.4972 0.3922 -0.0359 0.058 Uiso 1 1 calc R U . . .
N7 N 0.4573(4) 0.2500 0.1312(4) 0.0731(13) Uani 1 2 d S T P . .
C52 C 0.5215(5) 0.2500 0.1901(4) 0.0580(13) Uani 1 2 d S T P . .
C53 C 0.6042(5) 0.2500 0.2643(3) 0.0595(13) Uani 1 2 d S T P . .
H44 H 0.5557 0.2500 0.3069 0.089 Uiso 1 2 calc DR U P . .
H45 H 0.6562 0.2845 0.2680 0.089 Uiso 0.5 1 calc R U P . .
H46 H 0.6563 0.2155 0.2680 0.089 Uiso 0.5 1 calc R U P . .
N8 N 0.8564(8) 0.1911(5) 0.6323(5) 0.080(3) Uani 0.395(6) 1 d D U P B -1
C54 C 0.8651(7) 0.2136(4) 0.5742(5) 0.054(2) Uani 0.395(6) 1 d D U P B -1
C55 C 0.8711(19) 0.2390(9) 0.4979(4) 0.050(4) Uani 0.395(6) 1 d D U P B -1
H47 H 0.7881 0.2501 0.4730 0.075 Uiso 0.395(6) 1 calc DR U P B -1
H48 H 0.9050 0.2107 0.4653 0.075 Uiso 0.395(6) 1 calc R U P B -1
H49 H 0.9241 0.2732 0.5043 0.075 Uiso 0.395(6) 1 calc R U P B -1
N9 N 0.917(2) 0.2500 0.6668(14) 0.075(8) Uani 0.210(13) 2 d DS TU P B 2
C56 C 0.894(3) 0.2500 0.5975(16) 0.085(9) Uani 0.210(13) 2 d DS TU P B 2
C57 C 0.873(7) 0.2500 0.5123(19) 0.058(11) Uani 0.210(13) 2 d DS TU P B 2
H50 H 0.7846 0.2500 0.4930 0.087 Uiso 0.210(13) 2 calc DR U P B 2
H51 H 0.9108 0.2155 0.4935 0.087 Uiso 0.105(6) 1 calc R U P B 2
H52 H 0.9107 0.2845 0.4935 0.087 Uiso 0.105(6) 1 calc R U P B 2
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
O1 C1 C6 122.4(2) . . ?
O1 C1 C2 115.2(2) . . ?
C6 C1 C2 122.4(2) . . ?
O2 C2 C1 119.2(2) . . ?
O2 C2 C3 122.5(2) . . ?
C1 C2 C3 118.4(2) . . ?
C4 C3 C2 119.2(2) . . ?
C4 C3 C14 119.4(2) . . ?
C2 C3 C14 121.4(2) . . ?
C5 C4 C3 121.6(2) . . ?
C5 C4 H1 119.2 . . ?
C3 C4 H1 119.2 . . ?
C4 C5 C6 120.4(2) . . ?
C4 C5 H2 119.8 . . ?
C6 C5 H2 119.8 . . ?
C1 C6 C5 118.1(2) . . ?
C1 C6 C7 119.1(2) . . ?
C5 C6 C7 122.8(2) . . ?
C22 C7 C6 112.0(2) . . ?
C22 C7 C8 111.83(19) . . ?
C6 C7 C8 107.94(18) . . ?
C22 C7 C23 108.8(2) . . ?
C6 C7 C23 108.42(18) . . ?
C8 C7 C23 107.76(19) . . ?
C13 C8 C9 117.8(2) . . ?
C13 C8 C7 119.2(2) . . ?
C9 C8 C7 122.9(2) . . ?
C10 C9 C8 121.1(2) . . ?
C10 C9 H3 119.5 . . ?
C8 C9 H3 119.5 . . ?
C9 C10 C11 120.7(2) . . ?
C9 C10 H4 119.7 . . ?
C11 C10 H4 119.7 . . ?
C10 C11 C12 119.4(2) . . ?
C10 C11 C18 119.6(2) . . ?
C12 C11 C18 121.0(2) . . ?
O3 C12 C13 118.8(2) . . ?
O3 C12 C11 122.7(2) . . ?
C13 C12 C11 118.5(2) . . ?
C8 C13 O1 122.3(2) . . ?
C8 C13 C12 122.5(2) . . ?
O1 C13 C12 115.2(2) . . ?
C1 O1 C13 115.12(18) . . ?
C2 O2 H5 109.5 . . ?
N1 C14 C3 123.0(2) . . ?
N1 C14 H6 118.5 . . ?
C3 C14 H6 118.5 . . ?
C14 N1 C15 118.0(2) . . ?
C16 C15 C15 119.37(14) . 4_565 ?
C16 C15 N1 121.7(2) . . ?
C15 C15 N1 118.98(13) 4_565 . ?
C17 C16 C15 120.3(2) . . ?
C17 C16 H7 119.9 . . ?
C15 C16 H7 119.9 . . ?
C17 C17 C16 120.35(15) 4_565 . ?
C17 C17 H8 119.8 4_565 . ?
C16 C17 H8 119.8 . . ?
C12 O3 H9 109.5 . . ?
N2 C18 C11 121.2(2) . . ?
N2 C18 H10 119.4 . . ?
C11 C18 H10 119.4 . . ?
C18 N2 C19 118.8(2) . . ?
C20 C19 C19 119.56(14) . 4_565 ?
C20 C19 N2 122.4(2) . . ?
C19 C19 N2 118.06(12) 4_565 . ?
C21 C20 C19 120.3(2) . . ?
C21 C20 H11 119.9 . . ?
C19 C20 H11 119.9 . . ?
C21 C21 C20 120.15(15) 4_565 . ?
C21 C21 H12 119.9 4_565 . ?
C20 C21 H12 119.9 . . ?
C7 C22 H13 109.5 . . ?
C7 C22 H14 109.5 . . ?
H13 C22 H14 109.5 . . ?
C7 C22 H15 109.5 . . ?
H13 C22 H15 109.5 . . ?
H14 C22 H15 109.5 . . ?
C7 C23 H16 109.5 . . ?
C7 C23 H17 109.5 . . ?
H16 C23 H17 109.5 . . ?
C7 C23 H18 109.5 . . ?
H16 C23 H18 109.5 . . ?
H17 C23 H18 109.5 . . ?
O4 C24 C29 121.8(2) . . ?
O4 C24 C25 115.8(2) . . ?
C29 C24 C25 122.4(2) . . ?
O5 C25 C26 122.6(2) . . ?
O5 C25 C24 119.1(2) . . ?
C26 C25 C24 118.4(2) . . ?
C27 C26 C25 119.2(2) . . ?
C27 C26 C37 119.0(2) . . ?
C25 C26 C37 121.7(2) . . ?
C28 C27 C26 121.6(2) . . ?
C28 C27 H19 119.2 . . ?
C26 C27 H19 119.2 . . ?
C27 C28 C29 120.5(2) . . ?
C27 C28 H20 119.8 . . ?
C29 C28 H20 119.8 . . ?
C24 C29 C28 117.9(2) . . ?
C24 C29 C30 118.5(2) . . ?
C28 C29 C30 123.4(2) . . ?
C31 C30 C29 107.71(19) . . ?
C31 C30 C45 112.3(2) . . ?
C29 C30 C45 112.0(2) . . ?
C31 C30 C46 108.3(2) . . ?
C29 C30 C46 107.5(2) . . ?
C45 C30 C46 108.8(2) . . ?
C36 C31 C32 118.0(2) . . ?
C36 C31 C30 118.4(2) . . ?
C32 C31 C30 123.6(2) . . ?
C33 C32 C31 120.3(2) . . ?
C33 C32 H21 119.8 . . ?
C31 C32 H21 119.8 . . ?
C32 C33 C34 121.8(2) . . ?
C32 C33 H22 119.1 . . ?
C34 C33 H22 119.1 . . ?
C33 C34 C35 118.5(2) . . ?
C33 C34 C41 119.8(2) . . ?
C35 C34 C41 121.7(2) . . ?
O6 C35 C36 119.6(2) . . ?
O6 C35 C34 121.7(2) . . ?
C36 C35 C34 118.7(2) . . ?
O4 C36 C31 121.9(2) . . ?
O4 C36 C35 115.41(19) . . ?
C31 C36 C35 122.7(2) . . ?
C24 O4 C36 114.94(17) . . ?
C25 O5 H23 109.5 . . ?
N3 C37 C26 123.5(2) . . ?
N3 C37 H24 118.2 . . ?
C26 C37 H24 118.2 . . ?
C37 N3 C38 116.7(2) . . ?
C39 C38 C42 119.1(2) . 3_665 ?
C39 C38 N3 121.8(2) . . ?
C42 C38 N3 119.0(2) 3_665 . ?
C40 C39 C38 120.7(2) . . ?
C40 C39 H25 119.7 . . ?
C38 C39 H25 119.7 . . ?
C44 C40 C39 120.0(2) 3_665 . ?
C44 C40 H26 120.0 3_665 . ?
C39 C40 H26 120.0 . . ?
C35 O6 H27 109.5 . . ?
N4 C41 C34 122.8(2) . . ?
N4 C41 H28 118.6 . . ?
C34 C41 H28 118.6 . . ?
C41 N4 C42 117.3(2) . . ?
C43 C42 C38 119.1(2) . 3_665 ?
C43 C42 N4 122.2(2) . . ?
C38 C42 N4 118.7(2) 3_665 . ?
C44 C43 C42 120.8(2) . . ?
C44 C43 H29 119.6 . . ?
C42 C43 H29 119.6 . . ?
C43 C44 C40 120.0(2) . 3_665 ?
C43 C44 H30 120.0 . . ?
C40 C44 H30 120.0 3_665 . ?
C30 C45 H31 109.5 . . ?
C30 C45 H32 109.5 . . ?
H31 C45 H32 109.5 . . ?
C30 C45 H33 109.5 . . ?
H31 C45 H33 109.5 . . ?
H32 C45 H33 109.5 . . ?
C30 C46 H34 109.5 . . ?
C30 C46 H35 109.5 . . ?
H34 C46 H35 109.5 . . ?
C30 C46 H36 109.5 . . ?
H34 C46 H36 109.5 . . ?
H35 C46 H36 109.5 . . ?
Cl2 C47 Cl3 110.2(4) . . ?
Cl2 C47 Cl1 104.2(6) . . ?
Cl3 C47 Cl1 115.0(7) . . ?
Cl2 C47 H37 109.1 . . ?
Cl3 C47 H37 109.1 . . ?
Cl1 C47 H37 109.1 . . ?
N5 C48 C49 180.0(4) . . ?
C48 C49 H38 109.5 . . ?
C48 C49 H39 109.5 . . ?
H38 C49 H39 109.5 . . ?
C48 C49 H40 109.5 . . ?
H38 C49 H40 109.5 . . ?
H39 C49 H40 109.5 . . ?
N6 C50 C51 179.4(5) . . ?
C50 C51 H41 109.5 . . ?
C50 C51 H42 109.5 . . ?
H41 C51 H42 109.5 . . ?
C50 C51 H43 109.5 . . ?
H41 C51 H43 109.5 . . ?
H42 C51 H43 109.5 . . ?
N7 C52 C53 179.3(5) . . ?
C52 C53 H44 109.5 . . ?
C52 C53 H45 109.5 . . ?
H44 C53 H45 109.5 . . ?
C52 C53 H46 109.5 . . ?
H44 C53 H46 109.5 . . ?
H45 C53 H46 109.5 . . ?
N8 C54 C55 176.1(13) . . ?
C54 C55 H47 109.5 . . ?
C54 C55 H48 109.5 . . ?
H47 C55 H48 109.5 . . ?
C54 C55 H49 109.5 . . ?
H47 C55 H49 109.5 . . ?
H48 C55 H49 109.5 . . ?
N9 C56 C57 177(5) . . ?
C56 C57 H50 109.5 . . ?
C56 C57 H51 109.5 . . ?
H50 C57 H51 109.5 . . ?
C56 C57 H52 109.5 . . ?
H50 C57 H52 109.5 . . ?
H51 C57 H52 109.5 . . ?
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
C1 O1 1.387(3) . ?
C1 C6 1.389(3) . ?
C1 C2 1.402(3) . ?
C2 O2 1.350(3) . ?
C2 C3 1.406(3) . ?
C3 C4 1.393(3) . ?
C3 C14 1.447(3) . ?
C4 C5 1.375(3) . ?
C4 H1 0.9500 . ?
C5 C6 1.400(3) . ?
C5 H2 0.9500 . ?
C6 C7 1.526(3) . ?
C7 C22 1.519(3) . ?
C7 C8 1.528(3) . ?
C7 C23 1.550(3) . ?
C8 C13 1.388(3) . ?
C8 C9 1.400(3) . ?
C9 C10 1.380(3) . ?
C9 H3 0.9500 . ?
C10 C11 1.402(3) . ?
C10 H4 0.9500 . ?
C11 C12 1.403(3) . ?
C11 C18 1.455(3) . ?
C12 O3 1.344(3) . ?
C12 C13 1.400(3) . ?
C13 O1 1.390(3) . ?
O2 H5 0.8400 . ?
C14 N1 1.287(3) . ?
C14 H6 0.9500 . ?
N1 C15 1.421(3) . ?
C15 C16 1.400(3) . ?
C15 C15 1.401(5) 4_565 ?
C16 C17 1.382(4) . ?
C16 H7 0.9500 . ?
C17 C17 1.378(5) 4_565 ?
C17 H8 0.9500 . ?
O3 H9 0.8400 . ?
C18 N2 1.285(3) . ?
C18 H10 0.9500 . ?
N2 C19 1.417(3) . ?
C19 C20 1.396(3) . ?
C19 C19 1.399(5) 4_565 ?
C20 C21 1.386(3) . ?
C20 H11 0.9500 . ?
C21 C21 1.384(5) 4_565 ?
C21 H12 0.9500 . ?
C22 H13 0.9800 . ?
C22 H14 0.9800 . ?
C22 H15 0.9800 . ?
C23 H16 0.9800 . ?
C23 H17 0.9800 . ?
C23 H18 0.9800 . ?
C24 O4 1.388(3) . ?
C24 C29 1.389(3) . ?
C24 C25 1.398(3) . ?
C25 O5 1.347(3) . ?
C25 C26 1.398(3) . ?
C26 C27 1.395(4) . ?
C26 C37 1.443(3) . ?
C27 C28 1.368(4) . ?
C27 H19 0.9500 . ?
C28 C29 1.398(3) . ?
C28 H20 0.9500 . ?
C29 C30 1.522(3) . ?
C30 C31 1.516(3) . ?
C30 C45 1.534(3) . ?
C30 C46 1.545(3) . ?
C31 C36 1.390(3) . ?
C31 C32 1.396(3) . ?
C32 C33 1.375(4) . ?
C32 H21 0.9500 . ?
C33 C34 1.401(3) . ?
C33 H22 0.9500 . ?
C34 C35 1.408(3) . ?
C34 C41 1.442(3) . ?
C35 O6 1.357(3) . ?
C35 C36 1.391(3) . ?
C36 O4 1.389(3) . ?
O5 H23 0.8400 . ?
C37 N3 1.285(3) . ?
C37 H24 0.9500 . ?
N3 C38 1.420(3) . ?
C38 C39 1.398(4) . ?
C38 C42 1.404(3) 3_665 ?
C39 C40 1.384(4) . ?
C39 H25 0.9500 . ?
C40 C44 1.384(4) 3_665 ?
C40 H26 0.9500 . ?
O6 H27 0.8400 . ?
C41 N4 1.286(3) . ?
C41 H28 0.9500 . ?
N4 C42 1.418(3) . ?
C42 C43 1.398(3) . ?
C42 C38 1.404(3) 3_665 ?
C43 C44 1.383(4) . ?
C43 H29 0.9500 . ?
C44 C40 1.384(4) 3_665 ?
C44 H30 0.9500 . ?
C45 H31 0.9800 . ?
C45 H32 0.9800 . ?
C45 H33 0.9800 . ?
C46 H34 0.9800 . ?
C46 H35 0.9800 . ?
C46 H36 0.9800 . ?
Cl1 C47 1.763(14) . ?
Cl2 C47 1.730(7) . ?
Cl3 C47 1.746(6) . ?
N5 C48 1.140(5) . ?
C47 H37 1.0000 . ?
C48 C49 1.452(5) . ?
C49 H38 0.9800 . ?
C49 H39 0.9800 . ?
C49 H40 0.9800 . ?
N6 C50 1.135(5) . ?
C50 C51 1.443(4) . ?
C51 H41 0.9800 . ?
C51 H42 0.9800 . ?
C51 H43 0.9800 . ?
N7 C52 1.149(7) . ?
C52 C53 1.457(9) . ?
C53 H44 0.9800 . ?
C53 H45 0.9800 . ?
C53 H46 0.9800 . ?
N8 C54 1.157(10) . ?
C54 C55 1.465(13) . ?
C55 H47 0.9800 . ?
C55 H48 0.9800 . ?
C55 H49 0.9800 . ?
N9 C56 1.193(19) . ?
C56 C57 1.46(2) . ?
C57 H50 0.9800 . ?
C57 H51 0.9800 . ?
C57 H52 0.9800 . ?
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
O1 C1 C2 O2 -1.1(3) . . . . ?
C6 C1 C2 O2 178.4(2) . . . . ?
O1 C1 C2 C3 179.44(19) . . . . ?
C6 C1 C2 C3 -1.1(3) . . . . ?
O2 C2 C3 C4 -178.4(2) . . . . ?
C1 C2 C3 C4 1.1(3) . . . . ?
O2 C2 C3 C14 -1.4(3) . . . . ?
C1 C2 C3 C14 178.0(2) . . . . ?
C2 C3 C4 C5 0.1(3) . . . . ?
C14 C3 C4 C5 -176.9(2) . . . . ?
C3 C4 C5 C6 -1.3(4) . . . . ?
O1 C1 C6 C5 179.4(2) . . . . ?
C2 C1 C6 C5 0.0(3) . . . . ?
O1 C1 C6 C7 -3.8(3) . . . . ?
C2 C1 C6 C7 176.8(2) . . . . ?
C4 C5 C6 C1 1.2(3) . . . . ?
C4 C5 C6 C7 -175.5(2) . . . . ?
C1 C6 C7 C22 154.7(2) . . . . ?
C5 C6 C7 C22 -28.6(3) . . . . ?
C1 C6 C7 C8 31.2(3) . . . . ?
C5 C6 C7 C8 -152.2(2) . . . . ?
C1 C6 C7 C23 -85.3(2) . . . . ?
C5 C6 C7 C23 91.4(3) . . . . ?
C22 C7 C8 C13 -155.1(2) . . . . ?
C6 C7 C8 C13 -31.5(3) . . . . ?
C23 C7 C8 C13 85.4(2) . . . . ?
C22 C7 C8 C9 28.6(3) . . . . ?
C6 C7 C8 C9 152.3(2) . . . . ?
C23 C7 C8 C9 -90.8(3) . . . . ?
C13 C8 C9 C10 -1.5(3) . . . . ?
C7 C8 C9 C10 174.8(2) . . . . ?
C8 C9 C10 C11 0.1(4) . . . . ?
C9 C10 C11 C12 0.9(3) . . . . ?
C9 C10 C11 C18 -176.6(2) . . . . ?
C10 C11 C12 O3 -179.3(2) . . . . ?
C18 C11 C12 O3 -1.8(3) . . . . ?
C10 C11 C12 C13 -0.5(3) . . . . ?
C18 C11 C12 C13 177.0(2) . . . . ?
C9 C8 C13 O1 -179.2(2) . . . . ?
C7 C8 C13 O1 4.3(3) . . . . ?
C9 C8 C13 C12 2.0(3) . . . . ?
C7 C8 C13 C12 -174.5(2) . . . . ?
O3 C12 C13 C8 177.8(2) . . . . ?
C11 C12 C13 C8 -1.0(3) . . . . ?
O3 C12 C13 O1 -1.0(3) . . . . ?
C11 C12 C13 O1 -179.9(2) . . . . ?
C6 C1 O1 C13 -26.5(3) . . . . ?
C2 C1 O1 C13 152.95(19) . . . . ?
C8 C13 O1 C1 26.2(3) . . . . ?
C12 C13 O1 C1 -155.0(2) . . . . ?
C4 C3 C14 N1 173.2(2) . . . . ?
C2 C3 C14 N1 -3.8(4) . . . . ?
C3 C14 N1 C15 -179.5(2) . . . . ?
C14 N1 C15 C16 -38.6(3) . . . . ?
C14 N1 C15 C15 141.09(16) . . . 4_565 ?
C15 C15 C16 C17 -0.8(3) 4_565 . . . ?
N1 C15 C16 C17 178.9(2) . . . . ?
C15 C16 C17 C17 0.8(3) . . . 4_565 ?
C10 C11 C18 N2 178.5(2) . . . . ?
C12 C11 C18 N2 1.0(3) . . . . ?
C11 C18 N2 C19 -177.2(2) . . . . ?
C18 N2 C19 C20 49.7(3) . . . . ?
C18 N2 C19 C19 -130.57(17) . . . 4_565 ?
C19 C19 C20 C21 0.0(3) 4_565 . . . ?
N2 C19 C20 C21 179.8(2) . . . . ?
C19 C20 C21 C21 0.0(3) . . . 4_565 ?
O4 C24 C25 O5 -0.3(3) . . . . ?
C29 C24 C25 O5 179.0(2) . . . . ?
O4 C24 C25 C26 -179.7(2) . . . . ?
C29 C24 C25 C26 -0.3(4) . . . . ?
O5 C25 C26 C27 -179.5(2) . . . . ?
C24 C25 C26 C27 -0.1(4) . . . . ?
O5 C25 C26 C37 -1.5(4) . . . . ?
C24 C25 C26 C37 177.9(2) . . . . ?
C25 C26 C27 C28 -0.2(4) . . . . ?
C37 C26 C27 C28 -178.3(2) . . . . ?
C26 C27 C28 C29 1.1(4) . . . . ?
O4 C24 C29 C28 -179.5(2) . . . . ?
C25 C24 C29 C28 1.2(4) . . . . ?
O4 C24 C29 C30 3.7(3) . . . . ?
C25 C24 C29 C30 -175.7(2) . . . . ?
C27 C28 C29 C24 -1.6(4) . . . . ?
C27 C28 C29 C30 175.1(2) . . . . ?
C24 C29 C30 C31 -34.1(3) . . . . ?
C28 C29 C30 C31 149.2(2) . . . . ?
C24 C29 C30 C45 -158.1(2) . . . . ?
C28 C29 C30 C45 25.3(3) . . . . ?
C24 C29 C30 C46 82.4(3) . . . . ?
C28 C29 C30 C46 -94.3(3) . . . . ?
C29 C30 C31 C36 35.6(3) . . . . ?
C45 C30 C31 C36 159.5(2) . . . . ?
C46 C30 C31 C36 -80.4(3) . . . . ?
C29 C30 C31 C32 -147.9(2) . . . . ?
C45 C30 C31 C32 -24.1(3) . . . . ?
C46 C30 C31 C32 96.1(3) . . . . ?
C36 C31 C32 C33 2.2(3) . . . . ?
C30 C31 C32 C33 -174.2(2) . . . . ?
C31 C32 C33 C34 0.7(4) . . . . ?
C32 C33 C34 C35 -2.4(3) . . . . ?
C32 C33 C34 C41 179.8(2) . . . . ?
C33 C34 C35 O6 -179.4(2) . . . . ?
C41 C34 C35 O6 -1.6(3) . . . . ?
C33 C34 C35 C36 1.0(3) . . . . ?
C41 C34 C35 C36 178.8(2) . . . . ?
C32 C31 C36 O4 176.4(2) . . . . ?
C30 C31 C36 O4 -7.0(3) . . . . ?
C32 C31 C36 C35 -3.6(3) . . . . ?
C30 C31 C36 C35 173.0(2) . . . . ?
O6 C35 C36 O4 2.3(3) . . . . ?
C34 C35 C36 O4 -178.03(19) . . . . ?
O6 C35 C36 C31 -177.6(2) . . . . ?
C34 C35 C36 C31 2.0(3) . . . . ?
C29 C24 O4 C36 28.4(3) . . . . ?
C25 C24 O4 C36 -152.3(2) . . . . ?
C31 C36 O4 C24 -26.7(3) . . . . ?
C35 C36 O4 C24 153.3(2) . . . . ?
C27 C26 C37 N3 176.7(2) . . . . ?
C25 C26 C37 N3 -1.3(4) . . . . ?
C26 C37 N3 C38 -177.8(2) . . . . ?
C37 N3 C38 C39 39.1(3) . . . . ?
C37 N3 C38 C42 -142.4(2) . . . 3_665 ?
C42 C38 C39 C40 3.7(4) 3_665 . . . ?
N3 C38 C39 C40 -177.8(2) . . . . ?
C38 C39 C40 C44 1.3(4) . . . 3_665 ?
C33 C34 C41 N4 178.5(2) . . . . ?
C35 C34 C41 N4 0.7(4) . . . . ?
C34 C41 N4 C42 -177.4(2) . . . . ?
C41 N4 C42 C43 -38.3(3) . . . . ?
C41 N4 C42 C38 142.4(2) . . . 3_665 ?
C38 C42 C43 C44 -4.9(4) 3_665 . . . ?
N4 C42 C43 C44 175.8(2) . . . . ?
C42 C43 C44 C40 -0.1(4) . . . 3_665 ?
