#------------------------------------------------------------------------------
#$Date: 2020-09-04 01:51:13 +0300 (Fri, 04 Sep 2020) $
#$Revision: 255850 $
#$URL: file:///home/coder/svn-repositories/cod/cif/4/13/52/4135232.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_4135232
loop_
_publ_author_name
'Ma, Chun'
'Sheng, Feng-Tao'
'Wang, Hai-Qing'
'Deng, Shuang'
'Zhang, Yu-Chen'
'Jiao, Yinchun'
'Tan, Wei'
'Shi, Feng'
_publ_section_title
;
 Atroposelective Access to Oxindole-Based Axially Chiral Styrenes via the
 Strategy of Catalytic Kinetic Resolution.
;
_journal_name_full               'Journal of the American Chemical Society'
_journal_paper_doi               10.1021/jacs.0c00208
_journal_year                    2020
_chemical_formula_moiety         'C45 H33 Cl N4 O3, C H2 Cl2'
_chemical_formula_sum            'C46 H35 Cl3 N4 O3'
_chemical_formula_weight         798.13
_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   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2019-07-04
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_cell_angle_alpha                110.790(2)
_cell_angle_beta                 94.411(2)
_cell_angle_gamma                96.326(2)
_cell_formula_units_Z            2
_cell_length_a                   11.7169(15)
_cell_length_b                   13.0843(17)
_cell_length_c                   13.9715(18)
_cell_measurement_reflns_used    3756
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      26.71
_cell_measurement_theta_min      2.50
_cell_volume                     1974.7(4)
_computing_cell_refinement       'SAINT v7.68A (Bruker, 2009)'
_computing_data_reduction        'SAINT v7.68A (Bruker, 2009)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_diffrn_ambient_temperature      296.15
_diffrn_measured_fraction_theta_full 0.983
_diffrn_measured_fraction_theta_max 0.975
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0144
_diffrn_reflns_av_unetI/netI     0.0319
_diffrn_reflns_Laue_measured_fraction_full 0.983
_diffrn_reflns_Laue_measured_fraction_max 0.975
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            11079
_diffrn_reflns_point_group_measured_fraction_full 0.983
_diffrn_reflns_point_group_measured_fraction_max 0.975
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.372
_diffrn_reflns_theta_min         2.504
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.280
_exptl_absorpt_correction_T_max  0.7455
_exptl_absorpt_correction_T_min  0.6754
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
'SADABS-2008/1 (Bruker,2008) was used for absorption correction. wR2(int) was 0.0521 before and 0.0277 after correction. The Ratio of minimum to maximum transmission is 0.9060. The λ/2 correction factor is 0.0015.'
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.342
_exptl_crystal_description       block
_exptl_crystal_F_000             828
_refine_diff_density_max         0.994
_refine_diff_density_min         -0.602
_refine_diff_density_rms         0.050
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.045
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     505
_refine_ls_number_reflns         7872
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.045
_refine_ls_R_factor_all          0.0901
_refine_ls_R_factor_gt           0.0637
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0982P)²+1.0273P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1785
_refine_ls_wR_factor_ref         0.2009
_reflns_Friedel_coverage         0.000
_reflns_number_gt                5511
_reflns_number_total             7872
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            ja0c00208_si_003.cif
_cod_data_source_block           sf20190702b_0m
_cod_database_code               4135232
_shelx_shelxl_version_number     2016/6
_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.
;
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All N(H) groups
2.a Ternary CH refined with riding coordinates:
 C1(H1)
2.b Secondary CH2 refined with riding coordinates:
 C26(H26A,H26B), C46(H46A,H46B)
2.c Aromatic/amide H refined with riding coordinates:
 N2(H2), N3(H3), N4(H4), C4(H4A), C5(H5), C6(H6), C7(H7), C13(H13), C14(H14),
 C15(H15), C16(H16), C18(H18), C21(H21), C22(H22), C23(H23), C24(H24), C28(H28),
  C29(H29), C30(H30), C31(H31), C32(H32), C34(H34), C35(H35), C37(H37),
 C38(H38), C41(H41), C42(H42), C43(H43), C44(H44), C45(H45)
;
_olex2_submission_special_instructions 'No special instructions were received'
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 0.08930(9) 0.43027(9) 0.63485(9) 0.0886(3) Uani 1 1 d . . . . .
O1 O 0.44833(18) 0.57534(16) 0.68133(16) 0.0593(5) Uani 1 1 d . . . . .
O2 O 0.5198(2) 0.02262(18) 0.6535(2) 0.0913(9) Uani 1 1 d . . . . .
O3 O 0.2627(2) 0.12485(17) 0.89844(17) 0.0724(6) Uani 1 1 d . . . . .
N1 N 0.5990(2) 0.62946(18) 0.80989(17) 0.0512(6) Uani 1 1 d . . . . .
N2 N 0.3905(2) 0.40007(18) 0.50918(17) 0.0504(5) Uani 1 1 d . . . . .
H2 H 0.388109 0.466017 0.551375 0.060 Uiso 1 1 calc R . . . .
N3 N 0.5531(2) 0.20066(18) 0.66831(18) 0.0529(6) Uani 1 1 d . . . . .
H3 H 0.531416 0.263701 0.698722 0.063 Uiso 1 1 calc R . . . .
N4 N 0.3395(2) 0.04322(18) 0.75387(18) 0.0561(6) Uani 1 1 d . . . . .
H4 H 0.341643 -0.016999 0.702728 0.067 Uiso 1 1 calc R . . . .
C1 C 0.3999(2) 0.1464(2) 0.7542(2) 0.0499(6) Uani 1 1 d . . . . .
H1 H 0.436566 0.189245 0.824753 0.060 Uiso 1 1 calc R . . . .
C2 C 0.4972(3) 0.1157(2) 0.6853(2) 0.0526(7) Uani 1 1 d . . . . .
C3 C 0.6436(2) 0.2009(2) 0.6068(2) 0.0467(6) Uani 1 1 d . . . . .
C4 C 0.7183(3) 0.1225(2) 0.5862(2) 0.0578(7) Uani 1 1 d . . . . .
H4A H 0.709803 0.066237 0.612307 0.069 Uiso 1 1 calc R . . . .
C5 C 0.8059(3) 0.1293(3) 0.5261(3) 0.0646(8) Uani 1 1 d . . . . .
H5 H 0.856220 0.077134 0.512120 0.078 Uiso 1 1 calc R . . . .
C6 C 0.8192(3) 0.2117(3) 0.4870(2) 0.0637(8) Uani 1 1 d . . . . .
H6 H 0.878187 0.215257 0.446887 0.076 Uiso 1 1 calc R . . . .
C7 C 0.7447(3) 0.2895(2) 0.5075(2) 0.0563(7) Uani 1 1 d . . . . .
H7 H 0.753054 0.344812 0.480232 0.068 Uiso 1 1 calc R . . . .
C8 C 0.6570(2) 0.2857(2) 0.56863(19) 0.0449(6) Uani 1 1 d . . . . .
C9 C 0.5770(2) 0.3710(2) 0.59108(19) 0.0432(6) Uani 1 1 d . . . . .
C10 C 0.6060(2) 0.4631(2) 0.67945(19) 0.0434(6) Uani 1 1 d . . . . .
C11 C 0.5392(2) 0.5582(2) 0.7185(2) 0.0477(6) Uani 1 1 d . . . . .
C12 C 0.6992(2) 0.5913(2) 0.8359(2) 0.0495(6) Uani 1 1 d . . . . .
C13 C 0.7795(3) 0.6409(2) 0.9216(2) 0.0614(8) Uani 1 1 d . . . . .
H13 H 0.770556 0.707428 0.972452 0.074 Uiso 1 1 calc R . . . .
C14 C 0.8737(3) 0.5889(3) 0.9299(2) 0.0680(8) Uani 1 1 d . . . . .
H14 H 0.929353 0.620508 0.987414 0.082 Uiso 1 1 calc R . . . .
C15 C 0.8867(3) 0.4898(3) 0.8536(3) 0.0659(8) Uani 1 1 d . . . . .
H15 H 0.951442 0.456421 0.860314 0.079 Uiso 1 1 calc R . . . .
C16 C 0.8049(2) 0.4399(2) 0.7677(2) 0.0546(7) Uani 1 1 d . . . . .
H16 H 0.814663 0.373616 0.717101 0.065 Uiso 1 1 calc R . . . .
C17 C 0.7076(2) 0.4897(2) 0.75743(19) 0.0461(6) Uani 1 1 d . . . . .
C18 C 0.4505(3) 0.2369(2) 0.4327(2) 0.0520(7) Uani 1 1 d . . . . .
H18 H 0.494510 0.179506 0.417356 0.062 Uiso 1 1 calc R . . . .
C19 C 0.4773(2) 0.3379(2) 0.5141(2) 0.0467(6) Uani 1 1 d . . . . .
C20 C 0.3095(3) 0.3410(2) 0.4274(2) 0.0532(7) Uani 1 1 d . . . . .
C21 C 0.2070(3) 0.3684(3) 0.3925(3) 0.0662(8) Uani 1 1 d . . . . .
H21 H 0.184288 0.436900 0.425681 0.079 Uiso 1 1 calc R . . . .
C22 C 0.1410(3) 0.2908(4) 0.3074(3) 0.0815(11) Uani 1 1 d . . . . .
H22 H 0.071906 0.306726 0.282630 0.098 Uiso 1 1 calc R . . . .
C23 C 0.1753(4) 0.1873(3) 0.2566(3) 0.0841(11) Uani 1 1 d . . . . .
H23 H 0.128546 0.136711 0.198618 0.101 Uiso 1 1 calc R . . . .
C24 C 0.2747(3) 0.1596(3) 0.2900(3) 0.0722(9) Uani 1 1 d . . . . .
H24 H 0.296142 0.090793 0.255752 0.087 Uiso 1 1 calc R . . . .
C25 C 0.3446(3) 0.2368(2) 0.3772(2) 0.0554(7) Uani 1 1 d . . . . .
C26 C 0.5627(3) 0.7343(2) 0.8683(2) 0.0557(7) Uani 1 1 d . . . . .
H26A H 0.526121 0.762845 0.820413 0.067 Uiso 1 1 calc R . . . .
H26B H 0.630879 0.786647 0.905733 0.067 Uiso 1 1 calc R . . . .
C27 C 0.4799(2) 0.7272(2) 0.9442(2) 0.0492(6) Uani 1 1 d . . . . .
C28 C 0.4460(3) 0.6314(3) 0.9605(2) 0.0614(8) Uani 1 1 d . . . . .
H28 H 0.476183 0.567538 0.925288 0.074 Uiso 1 1 calc R . . . .
C29 C 0.3663(3) 0.6291(3) 1.0295(3) 0.0746(9) Uani 1 1 d . . . . .
H29 H 0.343248 0.563816 1.039740 0.090 Uiso 1 1 calc R . . . .
C30 C 0.3227(3) 0.7223(4) 1.0816(3) 0.0793(10) Uani 1 1 d . . . . .
H30 H 0.269981 0.720582 1.127644 0.095 Uiso 1 1 calc R . . . .
C31 C 0.3555(3) 0.8185(3) 1.0671(3) 0.0729(10) Uani 1 1 d . . . . .
H31 H 0.324752 0.881788 1.102800 0.087 Uiso 1 1 calc R . . . .
C32 C 0.4351(3) 0.8217(3) 0.9988(2) 0.0600(7) Uani 1 1 d . . . . .
H32 H 0.458233 0.887594 0.989663 0.072 Uiso 1 1 calc R . . . .
C33 C 0.3226(2) 0.2170(2) 0.7225(2) 0.0487(6) Uani 1 1 d . . . . .
C34 C 0.2640(3) 0.1828(2) 0.6234(2) 0.0567(7) Uani 1 1 d . . . . .
H34 H 0.273243 0.115065 0.574725 0.068 Uiso 1 1 calc R . . . .
C35 C 0.1925(3) 0.2475(3) 0.5961(2) 0.0590(7) Uani 1 1 d . . . . .
H35 H 0.152845 0.223194 0.529851 0.071 Uiso 1 1 calc R . . . .
C36 C 0.1805(3) 0.3481(2) 0.6678(3) 0.0597(7) Uani 1 1 d . . . . .
C37 C 0.2390(3) 0.3852(3) 0.7661(3) 0.0687(9) Uani 1 1 d . . . . .
H37 H 0.230941 0.453852 0.813824 0.082 Uiso 1 1 calc R . . . .
C38 C 0.3094(3) 0.3198(2) 0.7929(2) 0.0613(8) Uani 1 1 d . . . . .
H38 H 0.348937 0.344783 0.859169 0.074 Uiso 1 1 calc R . . . .
C39 C 0.2805(2) 0.0395(2) 0.8312(2) 0.0510(6) Uani 1 1 d . . . . .
C40 C 0.2369(2) -0.0718(2) 0.8316(2) 0.0481(6) Uani 1 1 d . . . . .
C41 C 0.2775(3) -0.1678(2) 0.7749(2) 0.0561(7) Uani 1 1 d . . . . .
H41 H 0.335123 -0.164529 0.733415 0.067 Uiso 1 1 calc R . . . .
C42 C 0.2337(3) -0.2686(3) 0.7787(3) 0.0657(8) Uani 1 1 d . . . . .
H42 H 0.261754 -0.332541 0.740292 0.079 Uiso 1 1 calc R . . . .
C43 C 0.1486(3) -0.2738(3) 0.8397(3) 0.0715(9) Uani 1 1 d . . . . .
H43 H 0.118250 -0.341444 0.842070 0.086 Uiso 1 1 calc R . . . .
C44 C 0.1081(3) -0.1795(3) 0.8970(3) 0.0720(9) Uani 1 1 d . . . . .
H44 H 0.050572 -0.183635 0.938369 0.086 Uiso 1 1 calc R . . . .
C45 C 0.1518(3) -0.0786(3) 0.8942(3) 0.0643(8) Uani 1 1 d . . . . .
H45 H 0.124379 -0.014933 0.934171 0.077 Uiso 1 1 calc R . . . .
Cl2 Cl -0.06999(15) 0.15967(19) 0.83794(14) 0.1769(9) Uani 1 1 d . . . . .
Cl3 Cl 0.00309(13) 0.00296(11) 0.66209(11) 0.1166(4) Uani 1 1 d . . . . .
C46 C 0.0190(4) 0.1387(4) 0.7486(4) 0.1120(15) Uani 1 1 d . . . . .
H46A H 0.097990 0.159931 0.782483 0.134 Uiso 1 1 calc R . . . .
H46B H 0.006190 0.186329 0.710433 0.134 Uiso 1 1 calc R . . . .
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'
Cl Cl 0.1484 0.1585 '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'
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
C11 N1 C12 111.8(2) . . ?
C11 N1 C26 122.6(2) . . ?
C12 N1 C26 125.6(2) . . ?
C19 N2 H2 125.2 . . ?
C20 N2 H2 125.2 . . ?
C20 N2 C19 109.6(2) . . ?
C2 N3 H3 115.7 . . ?
C2 N3 C3 128.6(2) . . ?
C3 N3 H3 115.7 . . ?
C1 N4 H4 119.2 . . ?
C39 N4 H4 119.2 . . ?
C39 N4 C1 121.6(2) . . ?
N4 C1 H1 107.6 . . ?
N4 C1 C2 106.5(2) . . ?
N4 C1 C33 114.3(2) . . ?
C2 C1 H1 107.6 . . ?
C33 C1 H1 107.6 . . ?
C33 C1 C2 113.0(2) . . ?
O2 C2 N3 124.9(3) . . ?
O2 C2 C1 121.1(3) . . ?
N3 C2 C1 113.9(2) . . ?
C4 C3 N3 122.6(2) . . ?
C4 C3 C8 120.4(2) . . ?
C8 C3 N3 117.0(2) . . ?
C3 C4 H4A 120.5 . . ?
C3 C4 C5 119.0(3) . . ?
C5 C4 H4A 120.5 . . ?
C4 C5 H5 119.5 . . ?
C6 C5 C4 121.1(3) . . ?
C6 C5 H5 119.5 . . ?
C5 C6 H6 120.2 . . ?
C5 C6 C7 119.7(3) . . ?
C7 C6 H6 120.2 . . ?
C6 C7 H7 119.7 . . ?
C6 C7 C8 120.5(3) . . ?
C8 C7 H7 119.7 . . ?
C3 C8 C7 119.2(2) . . ?
C3 C8 C9 120.7(2) . . ?
C7 C8 C9 120.1(2) . . ?
C10 C9 C8 117.6(2) . . ?
C10 C9 C19 130.6(2) . . ?
C19 C9 C8 111.7(2) . . ?
C9 C10 C11 127.2(2) . . ?
C9 C10 C17 127.8(2) . . ?
C17 C10 C11 105.0(2) . . ?
O1 C11 N1 122.7(2) . . ?
O1 C11 C10 130.4(2) . . ?
N1 C11 C10 106.9(2) . . ?
N1 C12 C17 108.7(2) . . ?
C13 C12 N1 127.9(3) . . ?
C13 C12 C17 123.4(3) . . ?
C12 C13 H13 121.1 . . ?
C12 C13 C14 117.7(3) . . ?
C14 C13 H13 121.1 . . ?
C13 C14 H14 119.6 . . ?
C13 C14 C15 120.9(3) . . ?
C15 C14 H14 119.6 . . ?
C14 C15 H15 119.5 . . ?
C16 C15 C14 121.0(3) . . ?
C16 C15 H15 119.5 . . ?
C15 C16 H16 120.2 . . ?
C15 C16 C17 119.7(3) . . ?
C17 C16 H16 120.2 . . ?
C12 C17 C10 107.6(2) . . ?
C16 C17 C10 135.1(2) . . ?
C16 C17 C12 117.3(3) . . ?
C19 C18 H18 126.0 . . ?
C19 C18 C25 107.9(3) . . ?
C25 C18 H18 126.0 . . ?
N2 C19 C9 126.2(2) . . ?
N2 C19 C18 107.9(2) . . ?
C18 C19 C9 125.9(3) . . ?
N2 C20 C21 130.3(3) . . ?
N2 C20 C25 108.1(3) . . ?
C21 C20 C25 121.6(3) . . ?
C20 C21 H21 121.3 . . ?
C22 C21 C20 117.4(3) . . ?
C22 C21 H21 121.3 . . ?
C21 C22 H22 119.2 . . ?
C21 C22 C23 121.5(3) . . ?
C23 C22 H22 119.2 . . ?
C22 C23 H23 119.2 . . ?
C24 C23 C22 121.6(3) . . ?
C24 C23 H23 119.2 . . ?
C23 C24 H24 120.7 . . ?
C23 C24 C25 118.6(3) . . ?
C25 C24 H24 120.7 . . ?
C18 C25 C20 106.5(2) . . ?
C24 C25 C18 134.2(3) . . ?
C24 C25 C20 119.3(3) . . ?
N1 C26 H26A 108.7 . . ?
N1 C26 H26B 108.7 . . ?
N1 C26 C27 114.1(2) . . ?
H26A C26 H26B 107.6 . . ?
C27 C26 H26A 108.7 . . ?
C27 C26 H26B 108.7 . . ?
C28 C27 C26 123.1(2) . . ?
C28 C27 C32 118.7(3) . . ?
C32 C27 C26 118.2(3) . . ?
C27 C28 H28 119.8 . . ?
C27 C28 C29 120.5(3) . . ?
C29 C28 H28 119.8 . . ?
C28 C29 H29 120.0 . . ?
C30 C29 C28 119.9(3) . . ?
C30 C29 H29 120.0 . . ?
C29 C30 H30 119.7 . . ?
C29 C30 C31 120.7(3) . . ?
C31 C30 H30 119.7 . . ?
C30 C31 H31 120.1 . . ?
C30 C31 C32 119.9(3) . . ?
C32 C31 H31 120.1 . . ?
C27 C32 C31 120.3(3) . . ?
C27 C32 H32 119.8 . . ?
C31 C32 H32 119.8 . . ?
C34 C33 C1 121.9(2) . . ?
C38 C33 C1 120.0(3) . . ?
C38 C33 C34 118.1(3) . . ?
C33 C34 H34 119.4 . . ?
C35 C34 C33 121.2(3) . . ?
C35 C34 H34 119.4 . . ?
C34 C35 H35 120.4 . . ?
C36 C35 C34 119.1(3) . . ?
C36 C35 H35 120.4 . . ?
C35 C36 Cl1 119.7(3) . . ?
C35 C36 C37 121.0(3) . . ?
C37 C36 Cl1 119.3(2) . . ?
C36 C37 H37 120.3 . . ?
C38 C37 C36 119.5(3) . . ?
C38 C37 H37 120.3 . . ?
C33 C38 H38 119.5 . . ?
C37 C38 C33 121.0(3) . . ?
C37 C38 H38 119.5 . . ?
O3 C39 N4 120.8(3) . . ?
O3 C39 C40 121.8(3) . . ?
N4 C39 C40 117.3(2) . . ?
C41 C40 C39 123.9(2) . . ?
C41 C40 C45 118.4(3) . . ?
C45 C40 C39 117.7(3) . . ?
C40 C41 H41 119.4 . . ?
C42 C41 C40 121.1(3) . . ?
C42 C41 H41 119.4 . . ?
C41 C42 H42 120.2 . . ?
C43 C42 C41 119.6(3) . . ?
C43 C42 H42 120.2 . . ?
C42 C43 H43 119.9 . . ?
C44 C43 C42 120.2(3) . . ?
C44 C43 H43 119.9 . . ?
C43 C44 H44 119.7 . . ?
C43 C44 C45 120.7(3) . . ?
C45 C44 H44 119.7 . . ?
C40 C45 H45 120.0 . . ?
C44 C45 C40 120.1(3) . . ?
C44 C45 H45 120.0 . . ?
Cl2 C46 Cl3 114.1(3) . . ?
Cl2 C46 H46A 108.7 . . ?
Cl2 C46 H46B 108.7 . . ?
Cl3 C46 H46A 108.7 . . ?
Cl3 C46 H46B 108.7 . . ?
H46A C46 H46B 107.6 . . ?
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 C36 1.743(3) . ?
O1 C11 1.226(3) . ?
O2 C2 1.207(3) . ?
O3 C39 1.228(3) . ?
N1 C11 1.365(4) . ?
N1 C12 1.398(4) . ?
N1 C26 1.454(3) . ?
N2 H2 0.8600 . ?
N2 C19 1.383(3) . ?
N2 C20 1.359(4) . ?
N3 H3 0.8600 . ?
N3 C2 1.331(4) . ?
N3 C3 1.416(3) . ?
N4 H4 0.8600 . ?
N4 C1 1.452(3) . ?
N4 C39 1.339(4) . ?
C1 H1 0.9800 . ?
C1 C2 1.543(4) . ?
C1 C33 1.511(4) . ?
C3 C4 1.389(4) . ?
C3 C8 1.390(4) . ?
C4 H4A 0.9300 . ?
C4 C5 1.390(4) . ?
C5 H5 0.9300 . ?
C5 C6 1.370(5) . ?
C6 H6 0.9300 . ?
C6 C7 1.381(4) . ?
C7 H7 0.9300 . ?
C7 C8 1.393(4) . ?
C8 C9 1.500(3) . ?
C9 C10 1.372(3) . ?
C9 C19 1.440(4) . ?
C10 C11 1.502(3) . ?
C10 C17 1.471(4) . ?
C12 C13 1.372(4) . ?
C12 C17 1.410(4) . ?
C13 H13 0.9300 . ?
C13 C14 1.378(5) . ?
C14 H14 0.9300 . ?
C14 C15 1.389(5) . ?
C15 H15 0.9300 . ?
C15 C16 1.384(4) . ?
C16 H16 0.9300 . ?
C16 C17 1.396(4) . ?
C18 H18 0.9300 . ?
C18 C19 1.388(4) . ?
C18 C25 1.411(4) . ?
C20 C21 1.393(4) . ?
C20 C25 1.417(4) . ?
C21 H21 0.9300 . ?
C21 C22 1.368(5) . ?
C22 H22 0.9300 . ?
C22 C23 1.407(6) . ?
C23 H23 0.9300 . ?
C23 C24 1.355(5) . ?
C24 H24 0.9300 . ?
C24 C25 1.402(4) . ?
C26 H26A 0.9700 . ?
C26 H26B 0.9700 . ?
C26 C27 1.511(4) . ?
C27 C28 1.374(4) . ?
C27 C32 1.386(4) . ?
C28 H28 0.9300 . ?
C28 C29 1.398(4) . ?
C29 H29 0.9300 . ?
C29 C30 1.358(5) . ?
C30 H30 0.9300 . ?
C30 C31 1.362(5) . ?
C31 H31 0.9300 . ?
C31 C32 1.393(5) . ?
C32 H32 0.9300 . ?
C33 C34 1.391(4) . ?
C33 C38 1.389(4) . ?
C34 H34 0.9300 . ?
C34 C35 1.379(4) . ?
C35 H35 0.9300 . ?
C35 C36 1.373(4) . ?
C36 C37 1.378(5) . ?
C37 H37 0.9300 . ?
C37 C38 1.374(4) . ?
C38 H38 0.9300 . ?
C39 C40 1.491(4) . ?
C40 C41 1.384(4) . ?
C40 C45 1.392(4) . ?
C41 H41 0.9300 . ?
C41 C42 1.383(4) . ?
C42 H42 0.9300 . ?
C42 C43 1.371(5) . ?
C43 H43 0.9300 . ?
C43 C44 1.368(5) . ?
C44 H44 0.9300 . ?
C44 C45 1.378(5) . ?
C45 H45 0.9300 . ?
Cl2 C46 1.655(5) . ?
Cl3 C46 1.737(5) . ?
C46 H46A 0.9700 . ?
C46 H46B 0.9700 . ?
