#------------------------------------------------------------------------------
#$Date: 2024-08-05 20:23:59 +0300 (Mon, 05 Aug 2024) $
#$Revision: 293688 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/13/33/7133317.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_7133317
loop_
_publ_author_name
'Wang, Yuxiang'
'Liao, Qi'
'Feng, Yabin'
'Wang, Yiran'
'Li, Yunzhi'
'Meng, Qi'
_publ_section_title
;
 Synthesis and resolution of multi-chiral carbonyl-N embedded
 hetero[7]helicenes for efficient circularly polarized luminescence.
;
_journal_issue                   63
_journal_name_full               'Chemical communications (Cambridge, England)'
_journal_page_first              8292
_journal_page_last               8295
_journal_paper_doi               10.1039/d4cc02747g
_journal_volume                  60
_journal_year                    2024
_chemical_absolute_configuration rm
_chemical_formula_moiety         'C H2 Cl2, C52 H26 N2 O4'
_chemical_formula_sum            'C53 H28 Cl2 N2 O4'
_chemical_formula_weight         827.67
_space_group_crystal_system      monoclinic
_space_group_IT_number           4
_space_group_name_Hall           'P 2yb'
_space_group_name_H-M_alt        'P 1 21 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2023-03-03
_audit_creation_method
;
Olex2 1.5-alpha
(compiled 2023.02.24 svn.rf166f9f3 for OlexSys, GUI svn.r6725)
;
_audit_update_record
;
2023-12-14 deposited with the CCDC.	2024-07-11 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 92.329(2)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   8.1505(5)
_cell_length_b                   11.3913(8)
_cell_length_c                   20.8223(13)
_cell_measurement_reflns_used    3822
_cell_measurement_temperature    100
_cell_measurement_theta_max      25.57
_cell_measurement_theta_min      2.65
_cell_volume                     1931.6(2)
_computing_cell_refinement       'SAINT V8.40A (Bruker, 2019)'
_computing_data_reduction        'SAINT V8.40A (Bruker, 2019)'
_computing_molecular_graphics    'Olex2 1.5-alpha (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5-alpha (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2019/2 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_diffrn_ambient_temperature      100
_diffrn_measured_fraction_theta_full 0.989
_diffrn_measured_fraction_theta_max 0.984
_diffrn_measurement_device_type  'D8 VENTURE'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0753
_diffrn_reflns_av_unetI/netI     0.1027
_diffrn_reflns_Laue_measured_fraction_full 0.989
_diffrn_reflns_Laue_measured_fraction_max 0.984
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       26
_diffrn_reflns_limit_l_min       -26
_diffrn_reflns_number            14940
_diffrn_reflns_point_group_measured_fraction_full 0.869
_diffrn_reflns_point_group_measured_fraction_max 0.852
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.415
_diffrn_reflns_theta_min         1.958
_diffrn_source_current           1.4
_diffrn_source_power             0.07
_diffrn_source_voltage           50.0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.223
_exptl_absorpt_correction_T_max  0.7454
_exptl_absorpt_correction_T_min  0.5455
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.1297 before and 0.0820 after correction.
The Ratio of minimum to maximum transmission is 0.7318.
The λ/2 correction factor is Not present.
;
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.423
_exptl_crystal_description       block
_exptl_crystal_F_000             852
_exptl_crystal_size_max          0.12
_exptl_crystal_size_mid          0.04
_exptl_crystal_size_min          0.02
_refine_diff_density_max         0.440
_refine_diff_density_min         -0.311
_refine_diff_density_rms         0.067
_refine_ls_abs_structure_details
;
 Flack x determined using 1510 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.08(8)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.051
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     550
_refine_ls_number_reflns         6770
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.051
_refine_ls_R_factor_all          0.0922
_refine_ls_R_factor_gt           0.0589
_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)+(0.0462P)²+0.6930P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1223
_refine_ls_wR_factor_ref         0.1453
_reflns_Friedel_coverage         0.645
_reflns_Friedel_fraction_full    0.737
_reflns_Friedel_fraction_max     0.706
_reflns_number_gt                4986
_reflns_number_total             6770
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d4cc02747g2.cif
_cod_data_source_block           tm1_0m
_cod_depositor_comments
'Adding full bibliography for 7133317--7133318.cif.'
_cod_database_code               7133317
_shelx_shelxl_version_number     2019/2
_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_max   0.996
_shelx_estimated_absorpt_t_min   0.974
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
2.a Secondary CH2 refined with riding coordinates:
 C53(H53A,H53B)
2.b Aromatic/amide H refined with riding coordinates:
 C6(H6), C8(H8), C26(H26), C19(H19), C52(H52), C43(H43), C49(H49), C2(H2),
 C13(H13), C16(H16), C14(H14), C39(H39), C46(H46), C7(H7), C18(H18), C27(H27),
 C15(H15), C38(H38), C50(H50), C37(H37), C44(H44), C28(H28), C3(H3), C51(H51),
 C45(H45), C5(H5)
;
_olex2_submission_special_instructions 'No special instructions were received'
loop_
_space_group_symop_operation_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_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
Cl2 Cl -0.0417(2) 0.65356(17) 0.34819(9) 0.0466(5) Uani 1 1 d . . . . .
Cl1 Cl 0.1388(2) 0.82719(19) 0.27584(9) 0.0518(5) Uani 1 1 d . . . . .
O2 O 0.5551(5) 0.4859(3) 0.13850(17) 0.0221(9) Uani 1 1 d . . . . .
O1 O 0.4411(5) 0.5868(3) 0.24811(17) 0.0237(9) Uani 1 1 d . . . . .
O4 O 0.7033(5) 0.2985(4) 0.09044(19) 0.0309(11) Uani 1 1 d . . . . .
O3 O 0.4562(6) 0.5961(4) 0.3749(2) 0.0387(12) Uani 1 1 d . . . . .
N2 N 0.7551(6) 0.3074(4) 0.3754(2) 0.0215(11) Uani 1 1 d . . . . .
N1 N 0.9588(6) 0.2770(4) 0.2637(2) 0.0226(11) Uani 1 1 d . . . . .
C21 C 0.6096(7) 0.4460(5) 0.1980(3) 0.0205(13) Uani 1 1 d . . . . .
C31 C 0.7254(7) 0.3645(5) 0.3166(3) 0.0203(13) Uani 1 1 d . . . . .
C32 C 0.8079(7) 0.3349(5) 0.2618(2) 0.0196(12) Uani 1 1 d . . . . .
C9 C 0.4733(7) 0.8125(5) 0.1229(3) 0.0218(13) Uani 1 1 d . . . . .
C10 C 0.4295(7) 0.7066(5) 0.1547(3) 0.0214(13) Uani 1 1 d . . . . .
C48 C 0.8067(7) 0.1779(5) 0.4584(3) 0.0244(14) Uani 1 1 d . . . . .
C12 C 0.1578(7) 0.6307(5) 0.1032(3) 0.0238(14) Uani 1 1 d . . . . .
C11 C 0.3235(7) 0.6144(5) 0.1253(3) 0.0219(13) Uani 1 1 d . . . . .
C17 C 0.0655(8) 0.5343(5) 0.0776(3) 0.0257(14) Uani 1 1 d . . . . .
C24 C 0.5536(7) 0.5144(5) 0.3749(3) 0.0249(14) Uani 1 1 d . . . . .
C41 C 1.0907(7) 0.2700(5) 0.3109(3) 0.0235(13) Uani 1 1 d . . . . .
C29 C 0.7467(7) 0.2881(5) 0.4852(3) 0.0237(13) Uani 1 1 d . . . . .
C22 C 0.5561(7) 0.4989(5) 0.2533(3) 0.0223(13) Uani 1 1 d . . . . .
C20 C 0.3877(7) 0.5018(5) 0.1233(3) 0.0217(13) Uani 1 1 d . . . . .
C1 C 0.4903(7) 0.6880(5) 0.2161(3) 0.0233(14) Uani 1 1 d . . . . .
C33 C 0.7360(7) 0.3617(5) 0.2002(3) 0.0222(13) Uani 1 1 d . . . . .
C23 C 0.6078(7) 0.4570(5) 0.3144(3) 0.0210(13) Uani 1 1 d . . . . .
C30 C 0.7116(7) 0.3601(5) 0.4315(3) 0.0231(13) Uani 1 1 d . . . . .
C47 C 0.8027(7) 0.1893(5) 0.3909(3) 0.0224(13) Uani 1 1 d . . . . .
C36 C 1.0061(7) 0.2147(5) 0.2104(3) 0.0246(13) Uani 1 1 d . . . . .
C42 C 1.2099(7) 0.1935(5) 0.2874(3) 0.0278(14) Uani 1 1 d . . . . .
C6 C 0.5658(8) 1.0236(5) 0.0626(3) 0.0280(14) Uani 1 1 d . . . . .
H6 H 0.592613 1.095417 0.042359 0.034 Uiso 1 1 calc R U . . .
C8 C 0.4257(7) 0.8362(6) 0.0586(3) 0.0253(13) Uani 1 1 d . . . . .
H8 H 0.359651 0.781235 0.034981 0.030 Uiso 1 1 calc R U . . .
C40 C 1.1547(7) 0.1573(6) 0.2233(3) 0.0274(14) Uani 1 1 d . . . . .
C26 C 0.5820(8) 0.5017(6) 0.4960(3) 0.0286(14) Uani 1 1 d . . . . .
H26 H 0.523841 0.573186 0.500848 0.034 Uiso 1 1 calc R U . . .
C19 C 0.2997(8) 0.4047(5) 0.0990(3) 0.0246(14) Uani 1 1 d . . . . .
H19 H 0.348488 0.329013 0.098442 0.030 Uiso 1 1 calc R U . . .
C34 C 0.7803(7) 0.2939(5) 0.1421(3) 0.0242(14) Uani 1 1 d . . . . .
C25 C 0.6232(7) 0.4642(5) 0.4347(3) 0.0247(14) Uani 1 1 d . . . . .
C52 C 0.8284(7) 0.0940(5) 0.3512(3) 0.0243(13) Uani 1 1 d . . . . .
H52 H 0.818438 0.100989 0.305772 0.029 Uiso 1 1 calc R U . . .
C43 C 1.1157(7) 0.3304(6) 0.3677(3) 0.0266(14) Uani 1 1 d . . . . .
H43 H 1.039433 0.387512 0.381182 0.032 Uiso 1 1 calc R U . . .
C49 C 0.8490(8) 0.0700(6) 0.4865(3) 0.0308(15) Uani 1 1 d . . . . .
H49 H 0.855197 0.061058 0.531910 0.037 Uiso 1 1 calc R U . . .
C2 C 0.5913(8) 0.7699(5) 0.2496(3) 0.0276(14) Uani 1 1 d . . . . .
H2 H 0.629999 0.753895 0.292388 0.033 Uiso 1 1 calc R U . . .
C13 C 0.0775(7) 0.7424(6) 0.1063(3) 0.0270(14) Uani 1 1 d . . . . .
H13 H 0.136029 0.807863 0.123803 0.032 Uiso 1 1 calc R U . . .
C4 C 0.5755(8) 0.8967(5) 0.1572(3) 0.0275(14) Uani 1 1 d . . . . .
C16 C -0.0963(8) 0.5506(6) 0.0562(3) 0.0309(16) Uani 1 1 d . . . . .
H16 H -0.157181 0.485732 0.039373 0.037 Uiso 1 1 calc R U . . .
C14 C -0.0814(7) 0.7564(6) 0.0845(3) 0.0313(15) Uani 1 1 d . . . . .
H14 H -0.132217 0.831266 0.086446 0.038 Uiso 1 1 calc R U . . .
C39 C 1.2164(8) 0.0871(6) 0.1749(3) 0.0337(16) Uani 1 1 d . . . . .
H39 H 1.315239 0.044034 0.182076 0.040 Uiso 1 1 calc R U . . .
C35 C 0.9220(7) 0.2156(5) 0.1515(3) 0.0250(14) Uani 1 1 d . . . . .
C46 C 1.3504(7) 0.1689(6) 0.3247(3) 0.0303(15) Uani 1 1 d . . . . .
H46 H 1.430746 0.116037 0.309969 0.036 Uiso 1 1 calc R U . . .
C7 C 0.4738(7) 0.9378(5) 0.0296(3) 0.0278(14) Uani 1 1 d . . . . .
H7 H 0.443554 0.950249 -0.014383 0.033 Uiso 1 1 calc R U . . .
C18 C 0.1415(8) 0.4219(6) 0.0761(3) 0.0268(14) Uani 1 1 d . . . . .
H18 H 0.081026 0.357095 0.058841 0.032 Uiso 1 1 calc R U . . .
C27 C 0.6258(8) 0.4349(6) 0.5500(3) 0.0336(16) Uani 1 1 d . . . . .
H27 H 0.602185 0.463872 0.591409 0.040 Uiso 1 1 calc R U . . .
C15 C -0.1705(7) 0.6593(6) 0.0590(3) 0.0338(16) Uani 1 1 d . . . . .
H15 H -0.281119 0.668933 0.043760 0.041 Uiso 1 1 calc R U . . .
C38 C 1.1298(8) 0.0817(6) 0.1160(3) 0.0319(15) Uani 1 1 d . . . . .
H38 H 1.170058 0.032688 0.083275 0.038 Uiso 1 1 calc R U . . .
C50 C 0.8814(8) -0.0229(6) 0.4467(3) 0.0324(15) Uani 1 1 d . . . . .
H50 H 0.912844 -0.096213 0.465078 0.039 Uiso 1 1 calc R U . . .
C37 C 0.9873(8) 0.1451(6) 0.1033(3) 0.0322(15) Uani 1 1 d . . . . .
H37 H 0.933483 0.140943 0.062027 0.039 Uiso 1 1 calc R U . . .
C44 C 1.2568(7) 0.3044(6) 0.4044(3) 0.0297(15) Uani 1 1 d . . . . .
H44 H 1.276281 0.342707 0.444523 0.036 Uiso 1 1 calc R U . . .
C28 C 0.7033(8) 0.3268(6) 0.5449(3) 0.0294(14) Uani 1 1 d . . . . .
H28 H 0.726076 0.280220 0.581988 0.035 Uiso 1 1 calc R U . . .
C3 C 0.6330(8) 0.8715(6) 0.2206(3) 0.0302(15) Uani 1 1 d . . . . .
H3 H 0.701600 0.926403 0.243221 0.036 Uiso 1 1 calc R U . . .
C51 C 0.8692(8) -0.0119(6) 0.3805(3) 0.0319(15) Uani 1 1 d . . . . .
H51 H 0.889171 -0.078509 0.354503 0.038 Uiso 1 1 calc R U . . .
C45 C 1.3709(8) 0.2227(6) 0.3833(3) 0.0340(16) Uani 1 1 d . . . . .
H45 H 1.464316 0.204092 0.410123 0.041 Uiso 1 1 calc R U . . .
C5 C 0.6172(8) 1.0013(6) 0.1260(3) 0.0301(15) Uani 1 1 d . . . . .
H5 H 0.682102 1.058099 0.148698 0.036 Uiso 1 1 calc R U . . .
C53 C 0.0944(11) 0.6751(8) 0.2872(4) 0.060(2) Uani 1 1 d . . . . .
H53A H 0.046647 0.642103 0.246649 0.072 Uiso 1 1 calc R U . . .
H53B H 0.197826 0.632531 0.297929 0.072 Uiso 1 1 calc R U . . .
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
C21 O2 C20 121.5(4) . . ?
C22 O1 C1 115.5(4) . . ?
C31 N2 C47 132.0(5) . . ?
C30 N2 C31 120.0(5) . . ?
C30 N2 C47 107.2(4) . . ?
C32 N1 C41 133.2(5) . . ?
C36 N1 C32 119.5(4) . . ?
C36 N1 C41 107.2(5) . . ?
O2 C21 C22 120.2(5) . . ?
O2 C21 C33 117.6(5) . . ?
C22 C21 C33 121.7(5) . . ?
N2 C31 C23 117.7(5) . . ?
C32 C31 N2 122.3(5) . . ?
C32 C31 C23 120.1(5) . . ?
N1 C32 C33 117.2(5) . . ?
C31 C32 N1 123.2(5) . . ?
C31 C32 C33 119.6(5) . . ?
C10 C9 C4 119.0(5) . . ?
C8 C9 C10 122.7(5) . . ?
C8 C9 C4 118.3(5) . . ?
C9 C10 C11 124.2(5) . . ?
C1 C10 C9 118.4(5) . . ?
C1 C10 C11 117.4(5) . . ?
C47 C48 C29 107.8(5) . . ?
C49 C48 C29 132.4(5) . . ?
C49 C48 C47 119.6(6) . . ?
C11 C12 C17 120.1(5) . . ?
C11 C12 C13 122.1(5) . . ?
C17 C12 C13 117.8(5) . . ?
C12 C11 C10 125.0(5) . . ?
C20 C11 C10 117.1(5) . . ?
C20 C11 C12 117.8(5) . . ?
C12 C17 C18 118.6(5) . . ?
C16 C17 C12 119.9(6) . . ?
C16 C17 C18 121.5(6) . . ?
O3 C24 C23 123.0(5) . . ?
O3 C24 C25 121.7(5) . . ?
C25 C24 C23 115.3(5) . . ?
C42 C41 N1 107.9(5) . . ?
C43 C41 N1 130.1(5) . . ?
C43 C41 C42 121.8(5) . . ?
C30 C29 C48 104.9(5) . . ?
C28 C29 C48 136.0(5) . . ?
C28 C29 C30 118.6(6) . . ?
O1 C22 C21 119.3(5) . . ?
O1 C22 C23 119.7(5) . . ?
C21 C22 C23 120.7(5) . . ?
O2 C20 C19 117.4(5) . . ?
C11 C20 O2 118.6(5) . . ?
C11 C20 C19 123.5(5) . . ?
O1 C1 C2 118.9(5) . . ?
C10 C1 O1 118.2(5) . . ?
C10 C1 C2 122.7(6) . . ?
C21 C33 C32 116.7(5) . . ?
C21 C33 C34 121.8(5) . . ?
C32 C33 C34 121.1(5) . . ?
C31 C23 C24 121.1(5) . . ?
C22 C23 C31 117.1(5) . . ?
C22 C23 C24 121.6(5) . . ?
N2 C30 C29 111.8(5) . . ?
N2 C30 C25 124.4(5) . . ?
C25 C30 C29 123.3(5) . . ?
C48 C47 N2 107.8(5) . . ?
C52 C47 N2 130.4(5) . . ?
C52 C47 C48 121.6(5) . . ?
N1 C36 C40 110.7(5) . . ?
C35 C36 N1 124.3(5) . . ?
C35 C36 C40 124.9(6) . . ?
C41 C42 C40 107.6(5) . . ?
C46 C42 C41 119.8(6) . . ?
C46 C42 C40 132.5(6) . . ?
C7 C6 H6 120.9 . . ?
C5 C6 H6 120.9 . . ?
C5 C6 C7 118.3(6) . . ?
C9 C8 H8 119.7 . . ?
C7 C8 C9 120.6(5) . . ?
C7 C8 H8 119.7 . . ?
C36 C40 C42 106.2(5) . . ?
C36 C40 C39 117.7(5) . . ?
C39 C40 C42 136.0(6) . . ?
C25 C26 H26 119.8 . . ?
C27 C26 H26 119.8 . . ?
C27 C26 C25 120.4(6) . . ?
C20 C19 H19 120.9 . . ?
C18 C19 C20 118.3(6) . . ?
C18 C19 H19 120.9 . . ?
O4 C34 C33 123.9(5) . . ?
O4 C34 C35 121.1(5) . . ?
C35 C34 C33 114.9(5) . . ?
C30 C25 C24 118.4(5) . . ?
C30 C25 C26 116.6(5) . . ?
C26 C25 C24 123.9(6) . . ?
C47 C52 H52 121.3 . . ?
C47 C52 C51 117.4(5) . . ?
C51 C52 H52 121.3 . . ?
C41 C43 H43 121.4 . . ?
C41 C43 C44 117.2(6) . . ?
C44 C43 H43 121.4 . . ?
C48 C49 H49 120.9 . . ?
C50 C49 C48 118.2(6) . . ?
C50 C49 H49 120.9 . . ?
C1 C2 H2 120.1 . . ?
C3 C2 C1 119.8(5) . . ?
C3 C2 H2 120.1 . . ?
C12 C13 H13 119.4 . . ?
C14 C13 C12 121.2(6) . . ?
C14 C13 H13 119.4 . . ?
C3 C4 C9 119.4(6) . . ?
C5 C4 C9 118.8(5) . . ?
C5 C4 C3 121.8(6) . . ?
C17 C16 H16 119.4 . . ?
C15 C16 C17 121.3(6) . . ?
C15 C16 H16 119.4 . . ?
C13 C14 H14 120.0 . . ?
C13 C14 C15 120.0(6) . . ?
C15 C14 H14 120.0 . . ?
C40 C39 H39 120.7 . . ?
C38 C39 C40 118.5(6) . . ?
C38 C39 H39 120.7 . . ?
C36 C35 C34 118.9(5) . . ?
C36 C35 C37 116.2(5) . . ?
C37 C35 C34 124.8(5) . . ?
C42 C46 H46 120.8 . . ?
C45 C46 C42 118.5(6) . . ?
C45 C46 H46 120.8 . . ?
C6 C7 H7 118.9 . . ?
C8 C7 C6 122.2(5) . . ?
C8 C7 H7 118.9 . . ?
C17 C18 H18 119.2 . . ?
C19 C18 C17 121.6(5) . . ?
C19 C18 H18 119.2 . . ?
C26 C27 H27 119.2 . . ?
C28 C27 C26 121.6(6) . . ?
C28 C27 H27 119.2 . . ?
C16 C15 C14 119.8(5) . . ?
C16 C15 H15 120.1 . . ?
C14 C15 H15 120.1 . . ?
C39 C38 H38 118.8 . . ?
C37 C38 C39 122.5(6) . . ?
C37 C38 H38 118.8 . . ?
C49 C50 H50 119.2 . . ?
C49 C50 C51 121.5(6) . . ?
C51 C50 H50 119.2 . . ?
C35 C37 H37 120.0 . . ?
C38 C37 C35 120.0(6) . . ?
C38 C37 H37 120.0 . . ?
C43 C44 H44 119.5 . . ?
C43 C44 C45 121.0(6) . . ?
C45 C44 H44 119.5 . . ?
C29 C28 C27 119.2(6) . . ?
C29 C28 H28 120.4 . . ?
C27 C28 H28 120.4 . . ?
C2 C3 C4 120.7(6) . . ?
C2 C3 H3 119.7 . . ?
C4 C3 H3 119.7 . . ?
C52 C51 H51 119.2 . . ?
C50 C51 C52 121.5(6) . . ?
C50 C51 H51 119.2 . . ?
C46 C45 C44 121.3(6) . . ?
C46 C45 H45 119.4 . . ?
C44 C45 H45 119.4 . . ?
C6 C5 C4 121.6(6) . . ?
C6 C5 H5 119.2 . . ?
C4 C5 H5 119.2 . . ?
Cl2 C53 Cl1 111.9(4) . . ?
Cl2 C53 H53A 109.2 . . ?
Cl2 C53 H53B 109.2 . . ?
Cl1 C53 H53A 109.2 . . ?
Cl1 C53 H53B 109.2 . . ?
H53A C53 H53B 107.9 . . ?
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
Cl2 C53 1.737(8) . ?
Cl1 C53 1.788(9) . ?
O2 C21 1.377(6) . ?
O2 C20 1.399(7) . ?
O1 C22 1.373(7) . ?
O1 C1 1.397(7) . ?
O4 C34 1.223(6) . ?
O3 C24 1.223(7) . ?
N2 C31 1.398(7) . ?
N2 C30 1.373(7) . ?
N2 C47 1.433(7) . ?
N1 C32 1.395(7) . ?
N1 C41 1.428(7) . ?
N1 C36 1.386(7) . ?
C21 C22 1.385(8) . ?
C21 C33 1.407(8) . ?
C31 C32 1.389(8) . ?
C31 C23 1.424(8) . ?
C32 C33 1.422(7) . ?
C9 C10 1.427(8) . ?
C9 C8 1.405(8) . ?
C9 C4 1.441(8) . ?
C10 C11 1.477(8) . ?
C10 C1 1.370(7) . ?
C48 C29 1.466(8) . ?
C48 C47 1.412(8) . ?
C48 C49 1.398(8) . ?
C12 C11 1.421(8) . ?
C12 C17 1.421(8) . ?
C12 C13 1.434(8) . ?
C11 C20 1.387(8) . ?
C17 C16 1.387(8) . ?
C17 C18 1.424(9) . ?
C24 C23 1.500(8) . ?
C24 C25 1.464(8) . ?
C41 C42 1.407(8) . ?
C41 C43 1.377(8) . ?
C29 C30 1.405(8) . ?
C29 C28 1.378(8) . ?
C22 C23 1.408(8) . ?
C20 C19 1.401(8) . ?
C1 C2 1.410(8) . ?
C33 C34 1.493(8) . ?
C30 C25 1.391(8) . ?
C47 C52 1.384(8) . ?
C36 C40 1.394(8) . ?
C36 C35 1.380(8) . ?
C42 C40 1.451(8) . ?
C42 C46 1.386(8) . ?
C6 H6 0.9500 . ?
C6 C7 1.396(8) . ?
C6 C5 1.391(9) . ?
C8 H8 0.9500 . ?
C8 C7 1.370(9) . ?
C40 C39 1.395(9) . ?
C26 H26 0.9500 . ?
C26 C25 1.400(8) . ?
C26 C27 1.392(9) . ?
C19 H19 0.9500 . ?
C19 C18 1.371(8) . ?
C34 C35 1.466(8) . ?
C52 H52 0.9500 . ?
C52 C51 1.386(9) . ?
C43 H43 0.9500 . ?
C43 C44 1.387(8) . ?
C49 H49 0.9500 . ?
C49 C50 1.376(9) . ?
C2 H2 0.9500 . ?
C2 C3 1.355(9) . ?
C13 H13 0.9500 . ?
C13 C14 1.364(8) . ?
C4 C3 1.414(8) . ?
C4 C5 1.405(9) . ?
C16 H16 0.9500 . ?
C16 C15 1.380(10) . ?
C14 H14 0.9500 . ?
C14 C15 1.414(9) . ?
C39 H39 0.9500 . ?
C39 C38 1.392(9) . ?
C35 C37 1.407(9) . ?
C46 H46 0.9500 . ?
C46 C45 1.368(9) . ?
C7 H7 0.9500 . ?
C18 H18 0.9500 . ?
C27 H27 0.9500 . ?
C27 C28 1.390(9) . ?
C15 H15 0.9500 . ?
C38 H38 0.9500 . ?
C38 C37 1.384(9) . ?
C50 H50 0.9500 . ?
C50 C51 1.383(9) . ?
C37 H37 0.9500 . ?
C44 H44 0.9500 . ?
C44 C45 1.400(9) . ?
C28 H28 0.9500 . ?
C3 H3 0.9500 . ?
C51 H51 0.9500 . ?
C45 H45 0.9500 . ?
C5 H5 0.9500 . ?
C53 H53A 0.9900 . ?
C53 H53B 0.9900 . ?
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
O2 C21 C22 O1 3.8(8) . . . . ?
O2 C21 C22 C23 178.4(5) . . . . ?
O2 C21 C33 C32 170.6(5) . . . . ?
O2 C21 C33 C34 -15.9(8) . . . . ?
O2 C20 C19 C18 -171.8(5) . . . . ?
O1 C22 C23 C31 179.0(5) . . . . ?
O1 C22 C23 C24 -6.4(8) . . . . ?
O1 C1 C2 C3 -176.4(5) . . . . ?
O4 C34 C35 C36 179.1(6) . . . . ?
O4 C34 C35 C37 3.4(10) . . . . ?
O3 C24 C23 C31 178.0(6) . . . . ?
O3 C24 C23 C22 3.7(9) . . . . ?
O3 C24 C25 C30 169.7(6) . . . . ?
O3 C24 C25 C26 2.0(10) . . . . ?
N2 C31 C32 N1 -21.6(9) . . . . ?
N2 C31 C32 C33 156.9(5) . . . . ?
N2 C31 C23 C24 17.0(8) . . . . ?
N2 C31 C23 C22 -168.4(5) . . . . ?
N2 C30 C25 C24 7.9(9) . . . . ?
N2 C30 C25 C26 176.6(6) . . . . ?
N2 C47 C52 C51 -177.9(6) . . . . ?
N1 C32 C33 C21 -163.4(5) . . . . ?
N1 C32 C33 C34 23.1(8) . . . . ?
N1 C41 C42 C40 2.9(7) . . . . ?
N1 C41 C42 C46 -178.6(5) . . . . ?
N1 C41 C43 C44 179.7(6) . . . . ?
N1 C36 C40 C42 -4.6(7) . . . . ?
N1 C36 C40 C39 177.8(5) . . . . ?
N1 C36 C35 C34 5.1(9) . . . . ?
N1 C36 C35 C37 -178.9(6) . . . . ?
C21 O2 C20 C11 100.5(6) . . . . ?
C21 O2 C20 C19 -87.4(6) . . . . ?
C21 C22 C23 C31 4.4(8) . . . . ?
C21 C22 C23 C24 178.9(5) . . . . ?
C21 C33 C34 O4 -6.4(9) . . . . ?
C21 C33 C34 C35 175.9(5) . . . . ?
C31 N2 C30 C29 178.3(5) . . . . ?
C31 N2 C30 C25 6.7(9) . . . . ?
C31 N2 C47 C48 -176.9(5) . . . . ?
C31 N2 C47 C52 -2.6(10) . . . . ?
C31 C32 C33 C21 18.0(8) . . . . ?
C31 C32 C33 C34 -155.5(6) . . . . ?
C32 N1 C41 C42 177.4(6) . . . . ?
C32 N1 C41 C43 -7.8(11) . . . . ?
C32 N1 C36 C40 -176.1(5) . . . . ?
C32 N1 C36 C35 7.5(9) . . . . ?
C32 C31 C23 C24 -161.9(5) . . . . ?
C32 C31 C23 C22 12.6(8) . . . . ?
C32 C33 C34 O4 166.8(6) . . . . ?
C32 C33 C34 C35 -10.9(8) . . . . ?
C9 C10 C11 C12 -60.8(8) . . . . ?
C9 C10 C11 C20 123.8(6) . . . . ?
C9 C10 C1 O1 177.1(5) . . . . ?
C9 C10 C1 C2 1.3(8) . . . . ?
C9 C8 C7 C6 -2.4(9) . . . . ?
C9 C4 C3 C2 -0.8(9) . . . . ?
C9 C4 C5 C6 -1.7(9) . . . . ?
C10 C9 C8 C7 -178.5(6) . . . . ?
C10 C9 C4 C3 1.4(8) . . . . ?
C10 C9 C4 C5 -179.5(6) . . . . ?
C10 C11 C20 O2 -10.8(7) . . . . ?
C10 C11 C20 C19 177.7(5) . . . . ?
C10 C1 C2 C3 -0.7(9) . . . . ?
C48 C29 C30 N2 -4.2(7) . . . . ?
C48 C29 C30 C25 167.5(5) . . . . ?
C48 C29 C28 C27 -169.9(6) . . . . ?
C48 C47 C52 C51 -4.2(9) . . . . ?
C48 C49 C50 C51 -1.5(10) . . . . ?
C12 C11 C20 O2 173.4(5) . . . . ?
C12 C11 C20 C19 1.9(8) . . . . ?
C12 C17 C16 C15 0.2(9) . . . . ?
C12 C17 C18 C19 0.5(8) . . . . ?
C12 C13 C14 C15 0.8(9) . . . . ?
C11 C10 C1 O1 -3.6(8) . . . . ?
C11 C10 C1 C2 -179.3(5) . . . . ?
C11 C12 C17 C16 179.8(5) . . . . ?
C11 C12 C17 C18 1.3(8) . . . . ?
C11 C12 C13 C14 179.7(6) . . . . ?
C11 C20 C19 C18 -0.2(8) . . . . ?
C17 C12 C11 C10 -177.8(5) . . . . ?
C17 C12 C11 C20 -2.5(8) . . . . ?
C17 C12 C13 C14 -1.0(8) . . . . ?
C17 C16 C15 C14 -0.5(9) . . . . ?
C41 N1 C32 C31 -25.9(10) . . . . ?
C41 N1 C32 C33 155.5(6) . . . . ?
C41 N1 C36 C40 6.4(7) . . . . ?
C41 N1 C36 C35 -170.0(6) . . . . ?
C41 C42 C40 C36 0.9(7) . . . . ?
C41 C42 C40 C39 177.8(7) . . . . ?
C41 C42 C46 C45 -1.5(9) . . . . ?
C41 C43 C44 C45 1.9(9) . . . . ?
C29 C48 C47 N2 4.9(6) . . . . ?
C29 C48 C47 C52 -170.1(5) . . . . ?
C29 C48 C49 C50 171.5(6) . . . . ?
C29 C30 C25 C24 -162.7(6) . . . . ?
C29 C30 C25 C26 5.9(8) . . . . ?
C22 O1 C1 C10 104.8(6) . . . . ?
C22 O1 C1 C2 -79.3(6) . . . . ?
C22 C21 C33 C32 -1.0(9) . . . . ?
C22 C21 C33 C34 172.5(6) . . . . ?
C20 O2 C21 C22 -50.6(7) . . . . ?
C20 O2 C21 C33 137.7(5) . . . . ?
C20 C19 C18 C17 -1.1(8) . . . . ?
C1 O1 C22 C21 -63.3(7) . . . . ?
C1 O1 C22 C23 122.0(5) . . . . ?
C1 C10 C11 C12 119.9(6) . . . . ?
C1 C10 C11 C20 -55.5(7) . . . . ?
C1 C2 C3 C4 0.4(9) . . . . ?
C33 C21 C22 O1 175.2(5) . . . . ?
C33 C21 C22 C23 -10.2(9) . . . . ?
C33 C34 C35 C36 -3.1(8) . . . . ?
C33 C34 C35 C37 -178.8(6) . . . . ?
C23 C31 C32 N1 157.3(5) . . . . ?
C23 C31 C32 C33 -24.2(8) . . . . ?
C23 C24 C25 C30 -9.1(8) . . . . ?
C23 C24 C25 C26 -176.9(6) . . . . ?
C30 N2 C31 C32 160.0(5) . . . . ?
C30 N2 C31 C23 -18.9(8) . . . . ?
C30 N2 C47 C48 -7.4(6) . . . . ?
C30 N2 C47 C52 166.9(6) . . . . ?
C30 C29 C28 C27 0.4(9) . . . . ?
C47 N2 C31 C32 -31.5(9) . . . . ?
C47 N2 C31 C23 149.5(6) . . . . ?
C47 N2 C30 C29 7.2(6) . . . . ?
C47 N2 C30 C25 -164.3(5) . . . . ?
C47 C48 C29 C30 -0.6(6) . . . . ?
C47 C48 C29 C28 170.6(7) . . . . ?
C47 C48 C49 C50 -1.7(9) . . . . ?
C47 C52 C51 C50 1.0(9) . . . . ?
C36 N1 C32 C31 157.4(6) . . . . ?
C36 N1 C32 C33 -21.1(8) . . . . ?
C36 N1 C41 C42 -5.7(7) . . . . ?
C36 N1 C41 C43 169.1(6) . . . . ?
C36 C40 C39 C38 2.3(9) . . . . ?
C36 C35 C37 C38 -1.2(9) . . . . ?
C42 C41 C43 C44 -6.1(9) . . . . ?
C42 C40 C39 C38 -174.4(7) . . . . ?
C42 C46 C45 C44 -2.7(10) . . . . ?
C8 C9 C10 C11 -3.5(9) . . . . ?
C8 C9 C10 C1 175.9(6) . . . . ?
C8 C9 C4 C3 -176.2(6) . . . . ?
C8 C9 C4 C5 2.9(8) . . . . ?
C40 C36 C35 C34 -170.9(6) . . . . ?
C40 C36 C35 C37 5.2(10) . . . . ?
C40 C42 C46 C45 176.6(6) . . . . ?
C40 C39 C38 C37 1.4(10) . . . . ?
C26 C27 C28 C29 4.0(10) . . . . ?
C34 C35 C37 C38 174.6(6) . . . . ?
C25 C24 C23 C31 -3.1(8) . . . . ?
C25 C24 C23 C22 -177.4(5) . . . . ?
C25 C26 C27 C28 -3.4(10) . . . . ?
C43 C41 C42 C40 -172.4(6) . . . . ?
C43 C41 C42 C46 6.1(9) . . . . ?
C43 C44 C45 C46 2.5(10) . . . . ?
C49 C48 C29 C30 -174.4(6) . . . . ?
C49 C48 C29 C28 -3.2(12) . . . . ?
C49 C48 C47 N2 179.6(5) . . . . ?
C49 C48 C47 C52 4.7(9) . . . . ?
C49 C50 C51 C52 1.9(10) . . . . ?
C13 C12 C11 C10 1.4(9) . . . . ?
C13 C12 C11 C20 176.8(5) . . . . ?
C13 C12 C17 C16 0.6(8) . . . . ?
C13 C12 C17 C18 -178.0(5) . . . . ?
C13 C14 C15 C16 0.0(9) . . . . ?
C4 C9 C10 C11 179.0(5) . . . . ?
C4 C9 C10 C1 -1.7(8) . . . . ?
C4 C9 C8 C7 -0.9(8) . . . . ?
C16 C17 C18 C19 -178.0(6) . . . . ?
C39 C38 C37 C35 -2.0(10) . . . . ?
C35 C36 C40 C42 171.8(6) . . . . ?
C35 C36 C40 C39 -5.8(10) . . . . ?
C46 C42 C40 C36 -177.3(7) . . . . ?
C46 C42 C40 C39 -0.4(13) . . . . ?
C7 C6 C5 C4 -1.5(9) . . . . ?
C18 C17 C16 C15 178.7(6) . . . . ?
C27 C26 C25 C24 166.6(6) . . . . ?
C27 C26 C25 C30 -1.4(9) . . . . ?
C28 C29 C30 N2 -177.2(5) . . . . ?
C28 C29 C30 C25 -5.5(9) . . . . ?
C3 C4 C5 C6 177.4(6) . . . . ?
C5 C6 C7 C8 3.6(9) . . . . ?
C5 C4 C3 C2 -179.9(6) . . . . ?
