#------------------------------------------------------------------------------
#$Date: 2018-09-10 03:46:29 +0200 (lun 10 de sep de 2018) $
#$Revision: 210722 $
#$URL: svn://www.crystallography.net/cod/cif/7/10/52/7105252.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_7105252
loop_
_publ_author_name
'Wang, Chao'
'Chen, Xiao-Hua'
'Zhou, Shi-Ming'
'Gong, Liu-Zhu'
_publ_section_title
;
 Asymmetric organocatalytic formal double-arylation of azomethines for the
 synthesis of highly enantiomerically enriched isoindolines
;
_journal_coden_ASTM              CHCOFS
_journal_issue                   8
_journal_name_full
;
 Chemical Communications (Cambridge, United Kingdom)
;
_journal_page_first              1275
_journal_page_last               1277
_journal_paper_doi               10.1039/b917246g
_journal_volume                  46
_journal_year                    2010
_chemical_absolute_configuration ad
_chemical_formula_sum            'C26 H21 Cl N2 O8'
_chemical_formula_weight         524.90
_space_group_IT_number           4
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  'P 2yb'
_symmetry_space_group_name_H-M   'P 1 21 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.000(5)
_cell_angle_beta                 101.631(5)
_cell_angle_gamma                90.000(5)
_cell_formula_units_Z            4
_cell_length_a                   7.965(5)
_cell_length_b                   30.381(5)
_cell_length_c                   10.583(5)
_cell_measurement_reflns_used    4971
_cell_measurement_temperature    295(2)
_cell_measurement_theta_max      62.6760
_cell_measurement_theta_min      2.9059
_cell_volume                     2508(2)
_computing_cell_refinement       'CrysAlisPro (Oxford Diffraction Ltd.)'
_computing_data_collection       'CrysAlisPro (Oxford Diffraction Ltd.)'
_computing_data_reduction        'CrysAlisPro (Oxford Diffraction Ltd.)'
_computing_molecular_graphics    'Ortep-3 (L. J. Farrugia, 2001)'
_computing_publication_material  SHELXL-97
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1997)'
_diffrn_ambient_temperature      295(2)
_diffrn_detector_area_resol_mean 15.9149
_diffrn_measured_fraction_theta_full 0.978
_diffrn_measured_fraction_theta_max 0.978
_diffrn_measurement_device_type  'Gemini S Ultra, Oxford Diffraction'
_diffrn_measurement_method       'ω scans'
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_source         'Enhance Ultra (Cu) X-ray Source'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0289
_diffrn_reflns_av_sigmaI/netI    0.0551
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_k_max       32
_diffrn_reflns_limit_k_min       -35
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            14302
_diffrn_reflns_theta_full        62.83
_diffrn_reflns_theta_max         62.83
_diffrn_reflns_theta_min         2.91
_exptl_absorpt_coefficient_mu    1.813
_exptl_absorpt_correction_T_max  0.7361
_exptl_absorpt_correction_T_min  0.6307
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro, Oxford Diffraction Ltd.,
Version 1.171.33.34d (release 27-02-2009 CrysAlis171 .NET)
(compiled Feb 27 2009,15:38:38)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.390
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             1088
_exptl_crystal_size_max          0.28
_exptl_crystal_size_mid          0.24
_exptl_crystal_size_min          0.18
_refine_diff_density_max         0.215
_refine_diff_density_min         -0.242
_refine_diff_density_rms         0.037
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.033(17)
_refine_ls_extinction_coef       0.00071(9)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_ref   1.005
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     676
_refine_ls_number_reflns         7313
_refine_ls_number_restraints     24
_refine_ls_restrained_S_all      1.052
_refine_ls_R_factor_all          0.0651
_refine_ls_R_factor_gt           0.0425
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0355P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0868
_refine_ls_wR_factor_ref         0.0934
_reflns_number_gt                5182
_reflns_number_total             7313
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            b917246g.txt
_cod_data_source_block           090305-cu2
_cod_original_sg_symbol_H-M      'P 21'
_cod_database_code               7105252
loop_
_symmetry_equiv_pos_as_xyz
'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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
Cl1 Cl 0.6696(2) -0.08344(6) 0.81241(16) 0.1164(6) Uani 1 1 d . . .
Cl2 Cl 0.81558(18) 0.38244(5) 1.24252(14) 0.0995(5) Uani 1 1 d . . .
O5 O 0.9069(3) 0.15724(9) 0.3624(3) 0.0597(7) Uani 1 1 d . . .
N3 N 0.8809(4) 0.23571(10) 0.7793(3) 0.0487(8) Uani 1 1 d D . .
O13 O 0.5624(3) 0.12748(9) 0.8717(3) 0.0547(7) Uani 1 1 d . . .
C4 C 0.5897(5) -0.00104(11) 0.4523(4) 0.0454(9) Uani 1 1 d . . .
C52 C 0.9099(4) 0.14436(12) 0.6898(4) 0.0476(9) Uani 1 1 d . . .
H52 H 0.8628 0.1637 0.6241 0.057 Uiso 1 1 calc R . .
C30 C 0.7547(4) 0.29802(11) 0.8854(4) 0.0422(9) Uani 1 1 d . . .
N1 N 0.4701(4) 0.07051(11) 0.3662(4) 0.0567(9) Uani 1 1 d D . .
C38 C 0.5874(4) 0.23923(12) 0.7448(4) 0.0414(9) Uani 1 1 d . . .
O12 O 0.3810(3) 0.28525(9) 0.6138(3) 0.0624(7) Uani 1 1 d . . .
O2 O 0.4391(4) -0.03449(11) 0.2220(3) 0.0849(9) Uani 1 1 d U . .
O9 O 0.7197(4) 0.33859(9) 0.6618(3) 0.0755(9) Uani 1 1 d U . .
O1 O 0.3661(4) 0.02997(12) 0.1259(3) 0.0857(10) Uani 1 1 d . . .
C42 C 0.5143(5) 0.16679(12) 0.8047(4) 0.0454(9) Uani 1 1 d . . .
C16 C 0.8838(5) 0.11406(13) 0.3160(4) 0.0518(10) Uani 1 1 d . . .
O16 O 1.1289(4) 0.02853(12) 0.6120(4) 0.0929(11) Uani 1 1 d . . .
C11 C 0.7392(4) 0.09155(13) 0.3339(4) 0.0456(9) Uani 1 1 d . . .
N4 N 1.1274(4) 0.03498(13) 0.7256(5) 0.0709(11) Uani 1 1 d . . .
C23 C 0.3745(5) 0.18633(15) 0.1305(5) 0.0668(12) Uani 1 1 d . . .
H23 H 0.3299 0.1863 0.0423 0.080 Uiso 1 1 calc R . .
C51 C 0.9791(4) 0.10440(13) 0.6600(4) 0.0542(10) Uani 1 1 d . . .
H51 H 0.9740 0.0962 0.5746 0.065 Uiso 1 1 calc R . .
O10 O 0.7635(5) 0.28172(11) 0.5436(3) 0.0874(10) Uani 1 1 d . . .
C17 C 0.9155(6) 0.19031(16) 0.2766(5) 0.0695(13) Uani 1 1 d . . .
C21 C 0.5080(4) 0.14907(12) 0.3227(4) 0.0470(9) Uani 1 1 d . . .
C43 C 0.2507(6) 0.31142(15) 0.6322(6) 0.0744(12) Uani 1 1 d U . .
C36 C 0.8271(4) 0.19758(11) 0.8491(4) 0.0455(9) Uani 1 1 d . . .
H36 H 0.8548 0.2029 0.9424 0.055 Uiso 1 1 calc R . .
C47 C 0.9115(4) 0.15516(11) 0.8171(4) 0.0415(9) Uani 1 1 d . . .
C7 C 0.5546(4) 0.02967(12) 0.3356(4) 0.0461(9) Uani 1 1 d . . .
C29 C 0.6171(5) 0.30593(13) 0.9444(5) 0.0627(12) Uani 1 1 d . . .
H29 H 0.5108 0.2938 0.9089 0.075 Uiso 1 1 calc R . .
C48 C 0.9919(5) 0.12704(13) 0.9134(4) 0.0551(10) Uani 1 1 d . . .
H48 H 0.9977 0.1347 0.9993 0.066 Uiso 1 1 calc R . .
C1 C 0.6414(6) -0.05176(14) 0.6727(5) 0.0665(12) Uani 1 1 d . . .
N2 N 0.2986(5) 0.26421(17) 0.1321(7) 0.0937(16) Uani 1 1 d . . .
C41 C 0.3445(5) 0.17524(13) 0.7503(4) 0.0581(11) Uani 1 1 d . . .
H41 H 0.2616 0.1541 0.7553 0.070 Uiso 1 1 calc R . .
C28 C 0.6339(6) 0.33131(15) 1.0544(5) 0.0679(12) Uani 1 1 d . . .
H28 H 0.5409 0.3361 1.0935 0.081 Uiso 1 1 calc R . .
C31 C 0.9099(5) 0.31694(12) 0.9402(4) 0.0508(10) Uani 1 1 d . . .
H31 H 1.0037 0.3125 0.9018 0.061 Uiso 1 1 calc R . .
C27 C 0.7905(5) 0.34934(13) 1.1045(4) 0.0570(11) Uani 1 1 d . . .
C24 C 0.3721(5) 0.22362(13) 0.2004(5) 0.0631(12) Uani 1 1 d . . .
C22 C 0.4435(5) 0.14859(14) 0.1911(4) 0.0639(12) Uani 1 1 d . . .
H22 H 0.4468 0.1229 0.1440 0.077 Uiso 1 1 calc R . .
C33 C 0.7429(4) 0.26898(11) 0.7643(4) 0.0432(9) Uani 1 1 d . . .
C50 C 1.0539(4) 0.07769(12) 0.7581(4) 0.0503(10) Uani 1 1 d . . .
C13 C 0.8370(5) 0.02737(13) 0.2405(4) 0.0537(10) Uani 1 1 d . . .
C6 C 0.4748(5) -0.03971(13) 0.6152(4) 0.0596(11) Uani 1 1 d . . .
H6 H 0.3820 -0.0486 0.6500 0.072 Uiso 1 1 calc R . .
C5 C 0.4515(5) -0.01425(13) 0.5051(4) 0.0524(10) Uani 1 1 d . . .
H5 H 0.3413 -0.0058 0.4655 0.063 Uiso 1 1 calc R . .
C14 C 0.9822(5) 0.04941(15) 0.2246(4) 0.0637(12) Uani 1 1 d . . .
H14 H 1.0638 0.0352 0.1875 0.076 Uiso 1 1 calc R . .
C3 C 0.7521(5) -0.01380(13) 0.5123(4) 0.0550(10) Uani 1 1 d . . .
H3 H 0.8459 -0.0050 0.4785 0.066 Uiso 1 1 calc R . .
O7 O 0.2903(6) 0.29693(13) 0.1963(6) 0.1324(19) Uani 1 1 d . . .
C2 C 0.7770(6) -0.03959(14) 0.6222(4) 0.0632(12) Uani 1 1 d . . .
H2 H 0.8869 -0.0485 0.6612 0.076 Uiso 1 1 calc R . .
C32 C 0.9297(5) 0.34240(13) 1.0507(4) 0.0549(11) Uani 1 1 d . . .
H32 H 1.0356 0.3545 1.0874 0.066 Uiso 1 1 calc R . .
C15 C 1.0064(5) 0.09277(15) 0.2640(4) 0.0600(11) Uani 1 1 d . . .
H15 H 1.1057 0.1075 0.2553 0.072 Uiso 1 1 calc R . .
C40 C 0.2967(5) 0.21450(14) 0.6888(4) 0.0586(11) Uani 1 1 d . . .
H40 H 0.1829 0.2194 0.6494 0.070 Uiso 1 1 calc R . .
C49 C 1.0631(5) 0.08811(13) 0.8850(4) 0.0605(11) Uani 1 1 d . . .
H49 H 1.1162 0.0693 0.9502 0.073 Uiso 1 1 calc R . .
C10 C 0.5888(4) 0.10795(12) 0.3882(4) 0.0488(10) Uani 1 1 d . . .
H10 H 0.6253 0.1133 0.4810 0.059 Uiso 1 1 calc R . .
C26 C 0.5011(6) 0.18725(14) 0.3903(5) 0.0679(12) Uani 1 1 d . . .
H26 H 0.5421 0.1875 0.4790 0.081 Uiso 1 1 calc R . .
C39 C 0.4190(5) 0.24663(12) 0.6861(4) 0.0500(10) Uani 1 1 d . . .
C37 C 0.6353(4) 0.19838(12) 0.8011(4) 0.0425(9) Uani 1 1 d . . .
C12 C 0.7177(4) 0.04791(12) 0.2977(4) 0.0464(9) Uani 1 1 d . . .
O6 O 0.9063(7) 0.18303(11) 0.1670(4) 0.139(2) Uani 1 1 d . . .
C25 C 0.4341(6) 0.22540(14) 0.3289(5) 0.0735(14) Uani 1 1 d . . .
H25 H 0.4319 0.2515 0.3746 0.088 Uiso 1 1 calc R . .
C34 C 0.7476(5) 0.29636(14) 0.6441(4) 0.0518(10) Uani 1 1 d . . .
C8 C 0.4420(5) 0.00877(16) 0.2149(5) 0.0599(11) Uani 1 1 d . . .
C9 C 0.3472(7) -0.05723(17) 0.1063(5) 0.0923(14) Uani 1 1 d U . .
H9A H 0.3538 -0.0885 0.1204 0.138 Uiso 1 1 calc R . .
H9B H 0.3984 -0.0499 0.0343 0.138 Uiso 1 1 calc R . .
H9C H 0.2293 -0.0482 0.0885 0.138 Uiso 1 1 calc R . .
C35 C 0.7072(6) 0.36768(16) 0.5508(5) 0.0849(13) Uani 1 1 d U . .
H35A H 0.6881 0.3973 0.5761 0.127 Uiso 1 1 calc R . .
H35B H 0.6133 0.3585 0.4841 0.127 Uiso 1 1 calc R . .
H35C H 0.8118 0.3664 0.5192 0.127 Uiso 1 1 calc R . .
C18 C 0.9409(7) 0.23353(16) 0.3392(5) 0.0908(16) Uani 1 1 d . . .
H18A H 0.9462 0.2302 0.4302 0.136 Uiso 1 1 calc R . .
H18B H 0.8470 0.2525 0.3033 0.136 Uiso 1 1 calc R . .
H18C H 1.0461 0.2462 0.3252 0.136 Uiso 1 1 calc R . .
C44 C 0.2218(7) 0.34731(18) 0.5327(6) 0.1013(16) Uani 1 1 d U . .
H44A H 0.3015 0.3440 0.4763 0.152 Uiso 1 1 calc R . .
H44B H 0.2384 0.3754 0.5747 0.152 Uiso 1 1 calc R . .
H44C H 0.1068 0.3454 0.4832 0.152 Uiso 1 1 calc R . .
O3 O 0.8016(4) -0.01515(9) 0.1919(3) 0.0669(8) Uani 1 1 d . . .
O14 O 0.5042(5) 0.08953(11) 0.6860(4) 0.0892(10) Uani 1 1 d . . .
O4 O 1.0391(5) -0.04266(13) 0.3162(5) 0.1114(13) Uani 1 1 d . . .
C45 C 0.5510(6) 0.08955(14) 0.7996(5) 0.0623(11) Uani 1 1 d . . .
O8 O 0.2538(6) 0.26270(15) 0.0158(6) 0.1244(18) Uani 1 1 d . . .
O15 O 1.1772(6) 0.00931(12) 0.8112(4) 0.1160(15) Uani 1 1 d . . .
C19 C 0.9136(7) -0.04820(16) 0.2361(5) 0.0764(14) Uani 1 1 d . . .
O11 O 0.1728(5) 0.30593(11) 0.7134(4) 0.0978(12) Uani 1 1 d . . .
C46 C 0.6051(6) 0.05123(15) 0.8849(5) 0.0839(15) Uani 1 1 d . . .
H46A H 0.6375 0.0611 0.9727 0.126 Uiso 1 1 calc R . .
H46B H 0.7010 0.0371 0.8598 0.126 Uiso 1 1 calc R . .
H46C H 0.5118 0.0308 0.8775 0.126 Uiso 1 1 calc R . .
C20 C 0.8545(9) -0.08954(17) 0.1667(6) 0.116(2) Uani 1 1 d . . .
H20A H 0.7487 -0.0842 0.1068 0.173 Uiso 1 1 calc R . .
H20B H 0.8370 -0.1116 0.2276 0.173 Uiso 1 1 calc R . .
H20C H 0.9395 -0.0995 0.1206 0.173 Uiso 1 1 calc R . .
H27 H 0.985(3) 0.2462(11) 0.807(3) 0.050(11) Uiso 1 1 d D . .
H1 H 0.405(6) 0.0654(18) 0.421(5) 0.12(2) Uiso 1 1 d D . .
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 '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 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cl Cl 0.3639 0.7018 '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
C17 O5 C16 118.5(3) . . ?
C33 N3 C36 107.7(3) . . ?
C33 N3 H27 115(2) . . ?
C36 N3 H27 118(2) . . ?
C45 O13 C42 116.9(3) . . ?
C3 C4 C5 118.7(4) . . ?
C3 C4 C7 123.1(3) . . ?
C5 C4 C7 118.0(3) . . ?
C47 C52 C51 120.0(4) . . ?
C47 C52 H52 120.0 . . ?
C51 C52 H52 120.0 . . ?
C31 C30 C29 117.4(3) . . ?
C31 C30 C33 119.1(3) . . ?
C29 C30 C33 123.4(3) . . ?
C10 N1 C7 112.2(3) . . ?
C10 N1 H1 119(4) . . ?
C7 N1 H1 111(4) . . ?
C39 C38 C37 119.7(3) . . ?
C39 C38 C33 131.2(3) . . ?
C37 C38 C33 109.1(3) . . ?
C43 O12 C39 120.1(3) . . ?
C8 O2 C9 115.7(4) . . ?
C34 O9 C35 117.5(4) . . ?
C37 C42 C41 119.6(3) . . ?
C37 C42 O13 119.3(3) . . ?
C41 C42 O13 120.9(3) . . ?
C15 C16 C11 120.0(4) . . ?
C15 C16 O5 121.8(3) . . ?
C11 C16 O5 117.9(3) . . ?
C12 C11 C16 119.7(3) . . ?
C12 C11 C10 111.0(3) . . ?
C16 C11 C10 129.3(4) . . ?
O15 N4 O16 124.8(4) . . ?
O15 N4 C50 118.5(5) . . ?
O16 N4 C50 116.7(4) . . ?
C24 C23 C22 119.5(4) . . ?
C24 C23 H23 120.3 . . ?
C22 C23 H23 120.3 . . ?
C50 C51 C52 118.7(4) . . ?
C50 C51 H51 120.7 . . ?
C52 C51 H51 120.7 . . ?
O6 C17 O5 121.3(4) . . ?
O6 C17 C18 126.4(5) . . ?
O5 C17 C18 112.3(4) . . ?
C26 C21 C22 119.2(4) . . ?
C26 C21 C10 121.3(4) . . ?
C22 C21 C10 119.4(3) . . ?
O11 C43 O12 123.9(5) . . ?
O11 C43 C44 126.2(5) . . ?
O12 C43 C44 109.9(5) . . ?
N3 C36 C37 101.2(3) . . ?
N3 C36 C47 111.4(3) . . ?
C37 C36 C47 113.6(3) . . ?
N3 C36 H36 110.1 . . ?
C37 C36 H36 110.1 . . ?
C47 C36 H36 110.1 . . ?
C48 C47 C52 118.9(3) . . ?
C48 C47 C36 121.2(3) . . ?
C52 C47 C36 120.0(3) . . ?
N1 C7 C4 110.7(3) . . ?
N1 C7 C12 101.6(3) . . ?
C4 C7 C12 113.8(3) . . ?
N1 C7 C8 108.2(3) . . ?
C4 C7 C8 113.5(3) . . ?
C12 C7 C8 108.2(3) . . ?
C28 C29 C30 121.6(4) . . ?
C28 C29 H29 119.2 . . ?
C30 C29 H29 119.2 . . ?
C49 C48 C47 121.4(4) . . ?
C49 C48 H48 119.3 . . ?
C47 C48 H48 119.3 . . ?
C2 C1 C6 121.5(4) . . ?
C2 C1 Cl1 120.8(4) . . ?
C6 C1 Cl1 117.7(3) . . ?
O8 N2 O7 124.2(5) . . ?
O8 N2 C24 118.0(6) . . ?
O7 N2 C24 117.8(6) . . ?
C40 C41 C42 120.8(4) . . ?
C40 C41 H41 119.6 . . ?
C42 C41 H41 119.6 . . ?
C27 C28 C29 118.5(4) . . ?
C27 C28 H28 120.8 . . ?
C29 C28 H28 120.8 . . ?
C30 C31 C32 121.8(3) . . ?
C30 C31 H31 119.1 . . ?
C32 C31 H31 119.1 . . ?
C32 C27 C28 122.1(4) . . ?
C32 C27 Cl2 118.2(3) . . ?
C28 C27 Cl2 119.7(3) . . ?
C25 C24 C23 122.7(4) . . ?
C25 C24 N2 118.9(5) . . ?
C23 C24 N2 118.4(5) . . ?
C23 C22 C21 119.6(4) . . ?
C23 C22 H22 120.2 . . ?
C21 C22 H22 120.2 . . ?
N3 C33 C38 100.2(3) . . ?
N3 C33 C34 108.6(3) . . ?
C38 C33 C34 111.7(3) . . ?
N3 C33 C30 112.5(3) . . ?
C38 C33 C30 111.5(3) . . ?
C34 C33 C30 111.9(3) . . ?
C51 C50 C49 122.8(3) . . ?
C51 C50 N4 118.4(4) . . ?
C49 C50 N4 118.8(4) . . ?
C12 C13 C14 120.4(4) . . ?
C12 C13 O3 118.4(3) . . ?
C14 C13 O3 121.1(4) . . ?
C5 C6 C1 118.1(4) . . ?
C5 C6 H6 121.0 . . ?
C1 C6 H6 121.0 . . ?
C6 C5 C4 121.2(4) . . ?
C6 C5 H5 119.4 . . ?
C4 C5 H5 119.4 . . ?
C13 C14 C15 119.7(4) . . ?
C13 C14 H14 120.1 . . ?
C15 C14 H14 120.1 . . ?
C4 C3 C2 120.6(4) . . ?
C4 C3 H3 119.7 . . ?
C2 C3 H3 119.7 . . ?
C1 C2 C3 119.9(4) . . ?
C1 C2 H2 120.1 . . ?
C3 C2 H2 120.1 . . ?
C27 C32 C31 118.5(4) . . ?
C27 C32 H32 120.8 . . ?
C31 C32 H32 120.8 . . ?
C16 C15 C14 120.1(4) . . ?
C16 C15 H15 119.9 . . ?
C14 C15 H15 119.9 . . ?
C41 C40 C39 119.5(4) . . ?
C41 C40 H40 120.2 . . ?
C39 C40 H40 120.2 . . ?
C50 C49 C48 118.2(4) . . ?
C50 C49 H49 120.9 . . ?
C48 C49 H49 120.9 . . ?
N1 C10 C21 111.6(3) . . ?
N1 C10 C11 102.7(3) . . ?
C21 C10 C11 113.3(3) . . ?
N1 C10 H10 109.7 . . ?
C21 C10 H10 109.7 . . ?
C11 C10 H10 109.7 . . ?
C21 C26 C25 121.1(4) . . ?
C21 C26 H26 119.4 . . ?
C25 C26 H26 119.4 . . ?
C38 C39 C40 120.1(4) . . ?
C38 C39 O12 117.8(3) . . ?
C40 C39 O12 121.8(4) . . ?
C42 C37 C38 120.2(3) . . ?
C42 C37 C36 130.6(3) . . ?
C38 C37 C36 109.2(3) . . ?
C13 C12 C11 120.0(3) . . ?
C13 C12 C7 130.3(3) . . ?
C11 C12 C7 109.7(3) . . ?
C24 C25 C26 117.9(4) . . ?
C24 C25 H25 121.1 . . ?
C26 C25 H25 121.1 . . ?
O10 C34 O9 122.9(4) . . ?
O10 C34 C33 124.7(4) . . ?
O9 C34 C33 112.2(3) . . ?
O1 C8 O2 124.7(4) . . ?
O1 C8 C7 123.1(4) . . ?
O2 C8 C7 112.2(4) . . ?
O2 C9 H9A 109.5 . . ?
O2 C9 H9B 109.5 . . ?
H9A C9 H9B 109.5 . . ?
O2 C9 H9C 109.5 . . ?
H9A C9 H9C 109.5 . . ?
H9B C9 H9C 109.5 . . ?
O9 C35 H35A 109.5 . . ?
O9 C35 H35B 109.5 . . ?
H35A C35 H35B 109.5 . . ?
O9 C35 H35C 109.5 . . ?
H35A C35 H35C 109.5 . . ?
H35B C35 H35C 109.5 . . ?
C17 C18 H18A 109.5 . . ?
C17 C18 H18B 109.5 . . ?
H18A C18 H18B 109.5 . . ?
C17 C18 H18C 109.5 . . ?
H18A C18 H18C 109.5 . . ?
H18B C18 H18C 109.5 . . ?
C43 C44 H44A 109.5 . . ?
C43 C44 H44B 109.5 . . ?
H44A C44 H44B 109.5 . . ?
C43 C44 H44C 109.5 . . ?
H44A C44 H44C 109.5 . . ?
H44B C44 H44C 109.5 . . ?
C19 O3 C13 119.1(4) . . ?
O14 C45 O13 122.4(4) . . ?
O14 C45 C46 127.7(5) . . ?
O13 C45 C46 110.0(4) . . ?
O4 C19 O3 122.7(5) . . ?
O4 C19 C20 127.8(5) . . ?
O3 C19 C20 109.5(5) . . ?
C45 C46 H46A 109.5 . . ?
C45 C46 H46B 109.5 . . ?
H46A C46 H46B 109.5 . . ?
C45 C46 H46C 109.5 . . ?
H46A C46 H46C 109.5 . . ?
H46B C46 H46C 109.5 . . ?
C19 C20 H20A 109.5 . . ?
C19 C20 H20B 109.5 . . ?
H20A C20 H20B 109.5 . . ?
C19 C20 H20C 109.5 . . ?
H20A C20 H20C 109.5 . . ?
H20B C20 H20C 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
Cl1 C1 1.740(5) . ?
Cl2 C27 1.751(4) . ?
O5 C17 1.365(5) . ?
O5 C16 1.400(5) . ?
N3 C33 1.478(4) . ?
N3 C36 1.484(5) . ?
N3 H27 0.88(2) . ?
O13 C45 1.375(5) . ?
O13 C42 1.402(4) . ?
C4 C3 1.376(5) . ?
C4 C5 1.391(5) . ?
C4 C7 1.528(5) . ?
C52 C47 1.385(5) . ?
C52 C51 1.395(5) . ?
C52 H52 0.9300 . ?
C30 C31 1.380(5) . ?
C30 C29 1.388(5) . ?
C30 C33 1.544(5) . ?
N1 C10 1.468(5) . ?
N1 C7 1.478(5) . ?
N1 H1 0.86(3) . ?
C38 C39 1.378(5) . ?
C38 C37 1.396(5) . ?
C38 C33 1.513(5) . ?
O12 C43 1.352(5) . ?
O12 C39 1.400(5) . ?
O2 C8 1.317(5) . ?
O2 C9 1.466(6) . ?
O9 C34 1.322(5) . ?
O9 C35 1.457(5) . ?
O1 C8 1.199(5) . ?
C42 C37 1.366(5) . ?
C42 C41 1.383(5) . ?
C16 C15 1.375(5) . ?
C16 C11 1.385(5) . ?
O16 N4 1.221(5) . ?
C11 C12 1.381(5) . ?
C11 C10 1.513(5) . ?
N4 O15 1.200(5) . ?
N4 C50 1.492(5) . ?
C23 C24 1.355(6) . ?
C23 C22 1.373(6) . ?
C23 H23 0.9300 . ?
C51 C50 1.357(6) . ?
C51 H51 0.9300 . ?
O10 C34 1.183(5) . ?
C17 O6 1.168(6) . ?
C17 C18 1.467(6) . ?
C21 C26 1.370(5) . ?
C21 C22 1.383(6) . ?
C21 C10 1.509(5) . ?
C43 O11 1.169(6) . ?
C43 C44 1.501(7) . ?
C36 C37 1.510(5) . ?
C36 C47 1.523(5) . ?
C36 H36 0.9800 . ?
C47 C48 1.384(5) . ?
C7 C12 1.538(5) . ?
C7 C8 1.542(6) . ?
C29 C28 1.380(6) . ?
C29 H29 0.9300 . ?
C48 C49 1.371(5) . ?
C48 H48 0.9300 . ?
C1 C2 1.350(6) . ?
C1 C6 1.392(6) . ?
N2 O8 1.211(7) . ?
N2 O7 1.214(7) . ?
N2 C24 1.488(6) . ?
C41 C40 1.375(6) . ?
C41 H41 0.9300 . ?
C28 C27 1.368(6) . ?
C28 H28 0.9300 . ?
C31 C32 1.384(5) . ?
C31 H31 0.9300 . ?
C27 C32 1.360(5) . ?
C24 C25 1.351(7) . ?
C22 H22 0.9300 . ?
C33 C34 1.526(6) . ?
C50 C49 1.367(6) . ?
C13 C12 1.375(5) . ?
C13 C14 1.376(6) . ?
C13 O3 1.398(5) . ?
C6 C5 1.379(6) . ?
C6 H6 0.9300 . ?
C5 H5 0.9300 . ?
C14 C15 1.383(6) . ?
C14 H14 0.9300 . ?
C3 C2 1.383(6) . ?
C3 H3 0.9300 . ?
C2 H2 0.9300 . ?
C32 H32 0.9300 . ?
C15 H15 0.9300 . ?
C40 C39 1.383(5) . ?
C40 H40 0.9300 . ?
C49 H49 0.9300 . ?
C10 H10 0.9800 . ?
C26 C25 1.382(6) . ?
C26 H26 0.9300 . ?
C25 H25 0.9300 . ?
C9 H9A 0.9600 . ?
C9 H9B 0.9600 . ?
C9 H9C 0.9600 . ?
C35 H35A 0.9600 . ?
C35 H35B 0.9600 . ?
C35 H35C 0.9600 . ?
C18 H18A 0.9600 . ?
C18 H18B 0.9600 . ?
C18 H18C 0.9600 . ?
C44 H44A 0.9600 . ?
C44 H44B 0.9600 . ?
C44 H44C 0.9600 . ?
O3 C19 1.361(6) . ?
O14 C45 1.186(6) . ?
O4 C19 1.186(6) . ?
C45 C46 1.483(6) . ?
C19 C20 1.483(7) . ?
C46 H46A 0.9600 . ?
C46 H46B 0.9600 . ?
C46 H46C 0.9600 . ?
C20 H20A 0.9600 . ?
C20 H20B 0.9600 . ?
C20 H20C 0.9600 . ?
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
C45 O13 C42 C37 -114.3(4) . . . . ?
C45 O13 C42 C41 70.4(5) . . . . ?
C17 O5 C16 C15 65.8(5) . . . . ?
C17 O5 C16 C11 -119.8(4) . . . . ?
C15 C16 C11 C12 -0.9(6) . . . . ?
O5 C16 C11 C12 -175.5(3) . . . . ?
C15 C16 C11 C10 -179.7(4) . . . . ?
O5 C16 C11 C10 5.8(6) . . . . ?
C47 C52 C51 C50 -2.9(5) . . . . ?
C16 O5 C17 O6 -1.0(7) . . . . ?
C16 O5 C17 C18 -179.7(4) . . . . ?
C39 O12 C43 O11 6.3(7) . . . . ?
C39 O12 C43 C44 -172.9(4) . . . . ?
C33 N3 C36 C37 32.7(4) . . . . ?
C33 N3 C36 C47 153.8(3) . . . . ?
C51 C52 C47 C48 4.0(5) . . . . ?
C51 C52 C47 C36 -176.6(3) . . . . ?
N3 C36 C47 C48 131.0(4) . . . . ?
C37 C36 C47 C48 -115.4(4) . . . . ?
N3 C36 C47 C52 -48.4(4) . . . . ?
C37 C36 C47 C52 65.1(4) . . . . ?
C10 N1 C7 C4 103.7(4) . . . . ?
C10 N1 C7 C12 -17.5(4) . . . . ?
C10 N1 C7 C8 -131.3(4) . . . . ?
C3 C4 C7 N1 -118.2(4) . . . . ?
C5 C4 C7 N1 57.5(4) . . . . ?
C3 C4 C7 C12 -4.5(5) . . . . ?
C5 C4 C7 C12 171.1(3) . . . . ?
C3 C4 C7 C8 119.9(4) . . . . ?
C5 C4 C7 C8 -64.4(4) . . . . ?
C31 C30 C29 C28 -0.7(6) . . . . ?
C33 C30 C29 C28 178.5(4) . . . . ?
C52 C47 C48 C49 -2.7(6) . . . . ?
C36 C47 C48 C49 177.8(4) . . . . ?
C37 C42 C41 C40 2.2(6) . . . . ?
O13 C42 C41 C40 177.5(4) . . . . ?
C30 C29 C28 C27 0.8(7) . . . . ?
C29 C30 C31 C32 0.9(6) . . . . ?
C33 C30 C31 C32 -178.4(3) . . . . ?
C29 C28 C27 C32 -1.1(7) . . . . ?
C29 C28 C27 Cl2 179.0(4) . . . . ?
C22 C23 C24 C25 -0.4(7) . . . . ?
C22 C23 C24 N2 179.2(4) . . . . ?
O8 N2 C24 C25 175.3(5) . . . . ?
O7 N2 C24 C25 -3.4(7) . . . . ?
O8 N2 C24 C23 -4.4(7) . . . . ?
O7 N2 C24 C23 176.9(5) . . . . ?
C24 C23 C22 C21 0.5(6) . . . . ?
C26 C21 C22 C23 0.4(6) . . . . ?
C10 C21 C22 C23 -178.0(4) . . . . ?
C36 N3 C33 C38 -35.5(4) . . . . ?
C36 N3 C33 C34 -152.7(3) . . . . ?
C36 N3 C33 C30 82.9(3) . . . . ?
C39 C38 C33 N3 -156.4(4) . . . . ?
C37 C38 C33 N3 24.7(4) . . . . ?
C39 C38 C33 C34 -41.6(5) . . . . ?
C37 C38 C33 C34 139.6(3) . . . . ?
C39 C38 C33 C30 84.4(5) . . . . ?
C37 C38 C33 C30 -94.5(4) . . . . ?
C31 C30 C33 N3 49.0(4) . . . . ?
C29 C30 C33 N3 -130.2(4) . . . . ?
C31 C30 C33 C38 160.6(3) . . . . ?
C29 C30 C33 C38 -18.6(5) . . . . ?
C31 C30 C33 C34 -73.6(4) . . . . ?
C29 C30 C33 C34 107.2(4) . . . . ?
C52 C51 C50 C49 0.6(6) . . . . ?
C52 C51 C50 N4 179.9(3) . . . . ?
O15 N4 C50 C51 -172.3(4) . . . . ?
O16 N4 C50 C51 6.4(5) . . . . ?
O15 N4 C50 C49 7.1(6) . . . . ?
O16 N4 C50 C49 -174.3(4) . . . . ?
C2 C1 C6 C5 -0.9(7) . . . . ?
Cl1 C1 C6 C5 179.4(3) . . . . ?
C1 C6 C5 C4 0.2(6) . . . . ?
C3 C4 C5 C6 -0.1(6) . . . . ?
C7 C4 C5 C6 -176.0(4) . . . . ?
C12 C13 C14 C15 -1.4(6) . . . . ?
O3 C13 C14 C15 174.5(4) . . . . ?
C5 C4 C3 C2 0.6(6) . . . . ?
C7 C4 C3 C2 176.2(4) . . . . ?
C6 C1 C2 C3 1.3(7) . . . . ?
Cl1 C1 C2 C3 -178.9(4) . . . . ?
C4 C3 C2 C1 -1.2(6) . . . . ?
C28 C27 C32 C31 1.3(6) . . . . ?
Cl2 C27 C32 C31 -178.8(3) . . . . ?
C30 C31 C32 C27 -1.2(6) . . . . ?
C11 C16 C15 C14 2.7(6) . . . . ?
O5 C16 C15 C14 177.0(4) . . . . ?
C13 C14 C15 C16 -1.5(6) . . . . ?
C42 C41 C40 C39 -2.7(6) . . . . ?
C51 C50 C49 C48 0.7(6) . . . . ?
N4 C50 C49 C48 -178.7(3) . . . . ?
C47 C48 C49 C50 0.4(6) . . . . ?
C7 N1 C10 C21 136.7(3) . . . . ?
C7 N1 C10 C11 15.0(4) . . . . ?
C26 C21 C10 N1 125.0(4) . . . . ?
C22 C21 C10 N1 -56.7(5) . . . . ?
C26 C21 C10 C11 -119.8(4) . . . . ?
C22 C21 C10 C11 58.6(5) . . . . ?
C12 C11 C10 N1 -5.9(4) . . . . ?
C16 C11 C10 N1 172.9(4) . . . . ?
C12 C11 C10 C21 -126.4(4) . . . . ?
C16 C11 C10 C21 52.5(5) . . . . ?
C22 C21 C26 C25 -1.4(6) . . . . ?
C10 C21 C26 C25 177.0(4) . . . . ?
C37 C38 C39 C40 3.3(6) . . . . ?
C33 C38 C39 C40 -175.4(4) . . . . ?
C37 C38 C39 O12 -170.3(3) . . . . ?
C33 C38 C39 O12 11.0(6) . . . . ?
C41 C40 C39 C38 -0.1(6) . . . . ?
C41 C40 C39 O12 173.3(4) . . . . ?
C43 O12 C39 C38 -131.0(4) . . . . ?
C43 O12 C39 C40 55.5(5) . . . . ?
C41 C42 C37 C38 1.1(6) . . . . ?
O13 C42 C37 C38 -174.3(3) . . . . ?
C41 C42 C37 C36 -178.3(4) . . . . ?
O13 C42 C37 C36 6.4(6) . . . . ?
C39 C38 C37 C42 -3.8(5) . . . . ?
C33 C38 C37 C42 175.2(3) . . . . ?
C39 C38 C37 C36 175.6(3) . . . . ?
C33 C38 C37 C36 -5.4(4) . . . . ?
N3 C36 C37 C42 163.1(4) . . . . ?
C47 C36 C37 C42 43.6(5) . . . . ?
N3 C36 C37 C38 -16.3(4) . . . . ?
C47 C36 C37 C38 -135.8(3) . . . . ?
C14 C13 C12 C11 3.2(6) . . . . ?
O3 C13 C12 C11 -172.9(4) . . . . ?
C14 C13 C12 C7 -174.7(4) . . . . ?
O3 C13 C12 C7 9.3(6) . . . . ?
C16 C11 C12 C13 -2.0(6) . . . . ?
C10 C11 C12 C13 177.0(3) . . . . ?
C16 C11 C12 C7 176.3(3) . . . . ?
C10 C11 C12 C7 -4.8(4) . . . . ?
N1 C7 C12 C13 -168.7(4) . . . . ?
C4 C7 C12 C13 72.3(5) . . . . ?
C8 C7 C12 C13 -54.9(5) . . . . ?
N1 C7 C12 C11 13.2(4) . . . . ?
C4 C7 C12 C11 -105.7(4) . . . . ?
C8 C7 C12 C11 127.0(4) . . . . ?
C23 C24 C25 C26 -0.6(7) . . . . ?
N2 C24 C25 C26 179.8(4) . . . . ?
C21 C26 C25 C24 1.5(7) . . . . ?
C35 O9 C34 O10 0.5(6) . . . . ?
C35 O9 C34 C33 -175.1(3) . . . . ?
N3 C33 C34 O10 44.7(5) . . . . ?
C38 C33 C34 O10 -64.9(5) . . . . ?
C30 C33 C34 O10 169.4(4) . . . . ?
N3 C33 C34 O9 -139.8(3) . . . . ?
C38 C33 C34 O9 110.6(4) . . . . ?
C30 C33 C34 O9 -15.1(4) . . . . ?
C9 O2 C8 O1 5.4(6) . . . . ?
C9 O2 C8 C7 -174.9(3) . . . . ?
N1 C7 C8 O1 37.7(5) . . . . ?
C4 C7 C8 O1 161.0(4) . . . . ?
C12 C7 C8 O1 -71.6(5) . . . . ?
N1 C7 C8 O2 -142.0(3) . . . . ?
C4 C7 C8 O2 -18.8(5) . . . . ?
C12 C7 C8 O2 108.6(4) . . . . ?
C12 C13 O3 C19 -122.7(4) . . . . ?
C14 C13 O3 C19 61.3(5) . . . . ?
C42 O13 C45 O14 0.5(6) . . . . ?
C42 O13 C45 C46 -179.6(3) . . . . ?
C13 O3 C19 O4 1.5(7) . . . . ?
C13 O3 C19 C20 -177.2(4) . . . . ?
