#------------------------------------------------------------------------------
#$Date: 2020-06-03 02:17:51 +0300 (Wed, 03 Jun 2020) $
#$Revision: 252551 $
#$URL: file:///home/coder/svn-repositories/cod/cif/4/03/84/4038452.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_4038452
loop_
_publ_author_name
'Sulfikarali, Thondikkal'
'Ajay, Jayaprakash'
'Suresh, Cherumuttathu H.'
'Bijina, Padinjare Veetil'
'Gokulnath, Sabapathi'
_publ_section_title
;
 Synthesis, Structure and Optical Properties of Di-m-benzihexaphyrins
 (1.1.0.0.0.0) and Di-m-benziheptaphyrins (1.0.1.0.0.0.0): Blackening of
 m-Phenylene Linked Dicarbaporphyrinoids by Simple p-Expansion.
;
_journal_name_full               'The Journal of organic chemistry'
_journal_paper_doi               10.1021/acs.joc.0c00754
_journal_year                    2020
_chemical_formula_moiety         'C53 H42 Cl3 N3 S2'
_chemical_formula_sum            'C53 H42 Cl3 N3 S2'
_chemical_formula_weight         891.36
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2ybc'
_space_group_name_H-M_alt        'P 1 21/c 1'
_atom_sites_solution_hydrogens   geom
_audit_creation_method           SHELXL-2018/3
_cell_angle_alpha                90
_cell_angle_beta                 110.411(4)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   18.677(3)
_cell_length_b                   12.7097(16)
_cell_length_c                   20.926(3)
_cell_measurement_reflns_used    4684
_cell_measurement_temperature    150(2)
_cell_measurement_theta_max      20.84
_cell_measurement_theta_min      2.33
_cell_volume                     4655.5(12)
_computing_cell_refinement       'APEX3/SAINT (Bruker, 2016)'
_computing_data_collection       'APEX3 (Bruker, 2016)'
_computing_data_reduction        'SAINT/XPREP (Bruker, 2016)'
_computing_molecular_graphics    'ORTEP3- 2014.1(Farrugia, 1997) '
_computing_publication_material  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_diffrn_ambient_temperature      150(2)
_diffrn_detector_area_resol_mean 0
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type  'Bruker KAPPA APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0828
_diffrn_reflns_av_unetI/netI     0.0741
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       22
_diffrn_reflns_limit_h_min       -22
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       24
_diffrn_reflns_limit_l_min       -24
_diffrn_reflns_number            45024
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_theta_full        24.998
_diffrn_reflns_theta_max         24.998
_diffrn_reflns_theta_min         1.909
_diffrn_source                   'sealed tube'
_exptl_absorpt_coefficient_mu    0.326
_exptl_absorpt_correction_T_max  0.989
_exptl_absorpt_correction_T_min  0.954
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS (Bruker, 2016)'
_exptl_crystal_colour            green
_exptl_crystal_density_diffrn    1.272
_exptl_crystal_density_meas      1.271
_exptl_crystal_density_method    none
_exptl_crystal_description       plate
_exptl_crystal_F_000             1856
_exptl_crystal_size_max          0.145
_exptl_crystal_size_mid          0.120
_exptl_crystal_size_min          0.035
_refine_diff_density_max         0.728
_refine_diff_density_min         -0.696
_refine_diff_density_rms         0.071
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.019
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     593
_refine_ls_number_reflns         8183
_refine_ls_number_restraints     150
_refine_ls_restrained_S_all      1.065
_refine_ls_R_factor_all          0.1441
_refine_ls_R_factor_gt           0.0764
_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)+(0.1306P)²+4.4471P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2006
_refine_ls_wR_factor_ref         0.2587
_reflns_Friedel_coverage         0.000
_reflns_number_gt                4452
_reflns_number_total             8183
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            jo0c00754_si_003.cif
_cod_data_source_block           shelx
_cod_original_cell_volume        4655.7(11)
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               4038452
_shelx_shelxl_version_number     2018/3
_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   0.954
_shelx_estimated_absorpt_t_max   0.989
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'
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 0.8143(3) 0.3661(4) 0.4265(2) 0.0476(12) Uani 1 1 d . . . . .
C2 C 0.8486(3) 0.2834(4) 0.4071(3) 0.0603(14) Uani 1 1 d . . . . .
H2 H 0.869030 0.286904 0.371466 0.072 Uiso 1 1 calc R U . . .
C3 C 0.8502(3) 0.1933(4) 0.4453(3) 0.0577(14) Uani 1 1 d . . . . .
H3 H 0.871322 0.128571 0.437596 0.069 Uiso 1 1 calc R U . . .
C4 C 0.8188(3) 0.2056(4) 0.4951(2) 0.0463(11) Uani 1 1 d . . . . .
C5 C 0.8175(3) 0.1250(4) 0.5432(2) 0.0463(11) Uani 1 1 d . . . . .
C6 C 0.7912(3) 0.1358(4) 0.5954(3) 0.0512(12) Uani 1 1 d . . . . .
C7 C 0.7938(4) 0.0560(4) 0.6454(3) 0.0690(16) Uani 1 1 d . . . . .
H7 H 0.814890 -0.012612 0.648278 0.083 Uiso 1 1 calc R U . . .
C8 C 0.7609(4) 0.0977(4) 0.6868(3) 0.0695(16) Uani 1 1 d . . . . .
H8 H 0.754394 0.064805 0.725144 0.083 Uiso 1 1 calc R U . . .
C9 C 0.7369(3) 0.2035(4) 0.6617(3) 0.0532(13) Uani 1 1 d . . . . .
C10 C 0.6928(3) 0.2718(4) 0.6907(2) 0.0513(12) Uani 1 1 d . . . . .
C11 C 0.6891(4) 0.2480(5) 0.7546(3) 0.0696(16) Uani 1 1 d . . . . .
H11 H 0.718088 0.190982 0.780139 0.084 Uiso 1 1 calc R U . . .
C12 C 0.6444(4) 0.3055(5) 0.7806(3) 0.0802(19) Uani 1 1 d . . . . .
H12 H 0.644465 0.290808 0.825116 0.096 Uiso 1 1 calc R U . . .
C13 C 0.5994(4) 0.3843(4) 0.7432(3) 0.0671(16) Uani 1 1 d . . . . .
H13 H 0.567708 0.422721 0.761862 0.081 Uiso 1 1 calc R U . . .
C14 C 0.5990(3) 0.4096(4) 0.6781(2) 0.0484(12) Uani 1 1 d . . . . .
C15 C 0.6481(3) 0.3542(4) 0.6534(2) 0.0483(12) Uani 1 1 d . . . . .
H15 H 0.651215 0.372669 0.610471 0.058 Uiso 1 1 calc R U . . .
C16 C 0.5454(3) 0.4885(4) 0.6389(2) 0.0458(11) Uani 1 1 d . . . . .
C17 C 0.4735(3) 0.5110(4) 0.6388(3) 0.0549(13) Uani 1 1 d . . . . .
H17 H 0.448455 0.475986 0.665250 0.066 Uiso 1 1 calc R U . . .
C18 C 0.4432(3) 0.5936(4) 0.5936(3) 0.0548(13) Uani 1 1 d . . . . .
H18 H 0.394535 0.625189 0.584303 0.066 Uiso 1 1 calc R U . . .
C19 C 0.4967(3) 0.6213(4) 0.5649(2) 0.0479(12) Uani 1 1 d . . . . .
C20 C 0.4935(3) 0.7069(4) 0.5170(2) 0.0484(12) Uani 1 1 d . . . . .
C21 C 0.4467(3) 0.7934(4) 0.5166(3) 0.0628(15) Uani 1 1 d . . . . .
H21 H 0.420010 0.795422 0.547756 0.075 Uiso 1 1 calc R U . . .
C22 C 0.4390(3) 0.8741(4) 0.4724(3) 0.0696(16) Uani 1 1 d . . . . .
H22 H 0.407689 0.932590 0.473363 0.084 Uiso 1 1 calc R U . . .
C23 C 0.4766(3) 0.8719(4) 0.4256(3) 0.0654(15) Uani 1 1 d . . . . .
H23 H 0.470450 0.928469 0.394427 0.078 Uiso 1 1 calc R U . . .
C24 C 0.5234(3) 0.7867(4) 0.4243(2) 0.0473(12) Uani 1 1 d . . . . .
C25 C 0.5315(3) 0.7051(4) 0.4711(2) 0.0447(11) Uani 1 1 d . . . . .
H25 H 0.563825 0.647289 0.471284 0.054 Uiso 1 1 calc R U . . .
C26 C 0.5587(3) 0.7857(4) 0.3722(2) 0.0451(11) Uani 1 1 d . . . . .
C27 C 0.5329(3) 0.8511(4) 0.3109(3) 0.0621(14) Uani 1 1 d . . . . .
H27 H 0.490146 0.897192 0.297314 0.075 Uiso 1 1 calc R U . . .
C28 C 0.5807(3) 0.8336(4) 0.2779(3) 0.0585(14) Uani 1 1 d . . . . .
H28 H 0.579187 0.865646 0.236412 0.070 Uiso 1 1 calc R U . . .
C29 C 0.6351(3) 0.7572(3) 0.3165(2) 0.0456(11) Uani 1 1 d . . . . .
C30 C 0.6937(3) 0.7183(3) 0.2994(2) 0.0434(11) Uani 1 1 d . . . . .
C31 C 0.7430(3) 0.6327(3) 0.3335(2) 0.0426(11) Uani 1 1 d . . . . .
C32 C 0.8079(3) 0.6037(4) 0.3215(3) 0.0527(13) Uani 1 1 d . . . . .
H32 H 0.828559 0.642570 0.293270 0.063 Uiso 1 1 calc R U . . .
C33 C 0.8406(3) 0.5107(4) 0.3553(3) 0.0562(13) Uani 1 1 d . . . . .
H33 H 0.885875 0.480320 0.352476 0.067 Uiso 1 1 calc R U . . .
C34 C 0.8006(3) 0.4682(3) 0.3928(2) 0.0454(11) Uani 1 1 d . . . . .
C35 C 0.8465(3) 0.0186(4) 0.5323(2) 0.0467(11) Uani 1 1 d . . . . .
C36 C 0.7946(3) -0.0557(4) 0.4940(3) 0.0541(13) Uani 1 1 d . . . . .
C37 C 0.8217(3) -0.1549(4) 0.4853(3) 0.0613(14) Uani 1 1 d . . . . .
H37 H 0.786359 -0.206520 0.459991 0.074 Uiso 1 1 calc R U . . .
C38 C 0.8971(3) -0.1801(4) 0.5118(3) 0.0628(14) Uani 1 1 d . . . . .
C39 C 0.9476(3) -0.1058(4) 0.5491(3) 0.0644(15) Uani 1 1 d . . . . .
H39 H 1.000225 -0.123404 0.568152 0.077 Uiso 1 1 calc R U . . .
C40 C 0.9245(3) -0.0058(4) 0.5602(3) 0.0543(13) Uani 1 1 d . . . . .
C41 C 0.7099(3) -0.0317(5) 0.4622(3) 0.0799(18) Uani 1 1 d . . . . .
H41A H 0.686006 -0.037830 0.496944 0.120 Uiso 1 1 calc R U . . .
H41B H 0.685984 -0.081845 0.425287 0.120 Uiso 1 1 calc R U . . .
H41C H 0.702934 0.039960 0.443770 0.120 Uiso 1 1 calc R U . . .
C42 C 0.9253(4) -0.2888(5) 0.4999(4) 0.099(2) Uani 1 1 d . . . . .
H42A H 0.931475 -0.333660 0.539589 0.149 Uiso 1 1 calc R U . . .
H42B H 0.974477 -0.281760 0.493301 0.149 Uiso 1 1 calc R U . . .
H42C H 0.887932 -0.320618 0.459260 0.149 Uiso 1 1 calc R U . . .
C43 C 0.9814(3) 0.0731(5) 0.6017(3) 0.0793(18) Uani 1 1 d . . . . .
H43A H 0.976977 0.079387 0.646861 0.119 Uiso 1 1 calc R U . . .
H43B H 0.971209 0.141549 0.578736 0.119 Uiso 1 1 calc R U . . .
H43C H 1.033070 0.049938 0.606642 0.119 Uiso 1 1 calc R U . . .
C44 C 0.7079(3) 0.7627(4) 0.2383(2) 0.0455(11) Uani 1 1 d . . . . .
C45 C 0.7499(3) 0.8547(4) 0.2433(3) 0.0583(14) Uani 1 1 d . . . . .
C46 C 0.7623(3) 0.8917(5) 0.1860(3) 0.0676(16) Uani 1 1 d . . . . .
H46 H 0.790162 0.955246 0.189187 0.081 Uiso 1 1 calc R U . . .
C47 C 0.7357(3) 0.8399(5) 0.1244(3) 0.0672(16) Uani 1 1 d . . . . .
C48 C 0.6929(3) 0.7501(5) 0.1201(3) 0.0650(16) Uani 1 1 d . . . . .
H48 H 0.673474 0.714117 0.077752 0.078 Uiso 1 1 calc R U . . .
C49 C 0.6774(3) 0.7107(4) 0.1757(2) 0.0544(13) Uani 1 1 d . . . . .
C50 C 0.6249(4) 0.6176(4) 0.1666(3) 0.0742(17) Uani 1 1 d . . . . .
H50A H 0.576781 0.640516 0.171160 0.111 Uiso 1 1 calc R U . . .
H50B H 0.649167 0.564677 0.201468 0.111 Uiso 1 1 calc R U . . .
H50C H 0.614491 0.587120 0.121240 0.111 Uiso 1 1 calc R U . . .
C51 C 0.7817(4) 0.9163(5) 0.3100(3) 0.087(2) Uani 1 1 d . . . . .
H51A H 0.739393 0.946807 0.321267 0.131 Uiso 1 1 calc R U . . .
H51B H 0.814970 0.972770 0.304756 0.131 Uiso 1 1 calc R U . . .
H51C H 0.811121 0.868900 0.346664 0.131 Uiso 1 1 calc R U . . .
C52 C 0.7510(5) 0.8828(6) 0.0627(3) 0.105(3) Uani 1 1 d . . . . .
H52A H 0.748560 0.959865 0.062836 0.157 Uiso 1 1 calc R U . . .
H52B H 0.712434 0.855775 0.020957 0.157 Uiso 1 1 calc R U . . .
H52C H 0.801881 0.860650 0.064337 0.157 Uiso 1 1 calc R U . . .
N1 N 0.7557(2) 0.2269(3) 0.60818(19) 0.0487(10) Uani 1 1 d . . . . .
N2 N 0.5577(2) 0.5559(3) 0.59203(19) 0.0471(10) Uani 1 1 d . . . . .
H2A H 0.599153 0.556617 0.581191 0.057 Uiso 1 1 calc R U . . .
N3 N 0.6186(2) 0.7291(3) 0.37464(19) 0.0436(9) Uani 1 1 d . . . . .
S1 S 0.72400(7) 0.54641(9) 0.38888(6) 0.0458(3) Uani 1 1 d . . . . .
S2 S 0.78532(8) 0.33298(9) 0.49358(6) 0.0500(4) Uani 1 1 d . . . . .
C53 C 0.9661(9) 0.3075(16) 0.7226(10) 0.283(12) Uani 0.666(6) 1 d D U P A 1
H53 H 0.940615 0.254513 0.686518 0.340 Uiso 0.666(6) 1 calc R U P A 1
Cl1 Cl 0.9750(8) 0.4294(12) 0.6861(7) 0.416(7) Uani 0.666(6) 1 d D U P A 1
Cl2 Cl 1.0601(5) 0.2628(7) 0.7757(4) 0.281(4) Uani 0.666(6) 1 d D U P A 1
Cl3 Cl 0.9066(3) 0.3458(6) 0.7649(3) 0.215(3) Uani 0.666(6) 1 d D U P A 1
C53' C 1.0146(16) 0.302(2) 0.7379(10) 0.301(15) Uani 0.334(6) 1 d D U P A 2
H53' H 1.061054 0.260439 0.740171 0.361 Uiso 0.334(6) 1 calc R U P A 2
Cl1' Cl 1.0391(15) 0.4068(18) 0.7965(10) 0.423(9) Uani 0.334(6) 1 d D U P A 2
Cl2' Cl 0.9501(12) 0.2224(14) 0.7627(9) 0.304(7) Uani 0.334(6) 1 d D U P A 2
Cl3' Cl 0.9713(9) 0.3573(11) 0.6560(6) 0.217(5) Uani 0.334(6) 1 d D U P A 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'
S S 0.1246 0.1234 '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
C2 C1 C34 124.4(4) . . ?
C2 C1 S2 111.6(4) . . ?
C34 C1 S2 124.0(3) . . ?
C1 C2 C3 112.4(5) . . ?
C4 C3 C2 114.5(4) . . ?
C3 C4 C5 124.4(4) . . ?
C3 C4 S2 109.8(4) . . ?
C5 C4 S2 125.7(4) . . ?
C6 C5 C4 126.2(4) . . ?
C6 C5 C35 117.7(4) . . ?
C4 C5 C35 116.1(4) . . ?
C5 C6 N1 124.5(4) . . ?
C5 C6 C7 125.7(5) . . ?
N1 C6 C7 109.8(4) . . ?
C8 C7 C6 106.5(5) . . ?
C7 C8 C9 106.7(5) . . ?
N1 C9 C8 112.0(4) . . ?
N1 C9 C10 124.9(4) . . ?
C8 C9 C10 123.1(5) . . ?
C15 C10 C11 118.5(5) . . ?
C15 C10 C9 121.8(4) . . ?
C11 C10 C9 119.4(5) . . ?
C12 C11 C10 120.7(5) . . ?
C11 C12 C13 120.5(5) . . ?
C12 C13 C14 121.4(5) . . ?
C15 C14 C13 117.7(5) . . ?
C15 C14 C16 123.6(4) . . ?
C13 C14 C16 118.7(4) . . ?
C14 C15 C10 121.1(4) . . ?
C17 C16 N2 106.0(4) . . ?
C17 C16 C14 128.7(4) . . ?
N2 C16 C14 125.3(4) . . ?
C16 C17 C18 108.8(4) . . ?
C19 C18 C17 107.7(4) . . ?
N2 C19 C18 106.8(4) . . ?
N2 C19 C20 124.5(4) . . ?
C18 C19 C20 128.6(5) . . ?
C25 C20 C21 118.6(5) . . ?
C25 C20 C19 123.7(4) . . ?
C21 C20 C19 117.7(4) . . ?
C22 C21 C20 121.1(5) . . ?
C21 C22 C23 120.4(5) . . ?
C22 C23 C24 120.1(5) . . ?
C25 C24 C23 118.5(4) . . ?
C25 C24 C26 123.4(4) . . ?
C23 C24 C26 118.1(4) . . ?
C20 C25 C24 121.3(4) . . ?
N3 C26 C24 125.2(4) . . ?
N3 C26 C27 111.1(4) . . ?
C24 C26 C27 123.7(4) . . ?
C28 C27 C26 106.7(5) . . ?
C27 C28 C29 107.1(5) . . ?
C30 C29 N3 125.3(4) . . ?
C30 C29 C28 125.2(4) . . ?
N3 C29 C28 109.6(4) . . ?
C29 C30 C31 125.3(4) . . ?
C29 C30 C44 119.0(4) . . ?
C31 C30 C44 115.7(4) . . ?
C32 C31 C30 124.3(4) . . ?
C32 C31 S1 110.8(3) . . ?
C30 C31 S1 124.6(3) . . ?
C31 C32 C33 113.1(4) . . ?
C34 C33 C32 113.1(4) . . ?
C33 C34 C1 126.1(4) . . ?
C33 C34 S1 110.8(3) . . ?
C1 C34 S1 122.8(4) . . ?
C36 C35 C40 120.2(4) . . ?
C36 C35 C5 118.9(4) . . ?
C40 C35 C5 120.9(4) . . ?
C35 C36 C37 118.6(5) . . ?
C35 C36 C41 121.8(5) . . ?
C37 C36 C41 119.6(5) . . ?
C38 C37 C36 122.1(5) . . ?
C37 C38 C39 118.6(5) . . ?
C37 C38 C42 120.8(6) . . ?
C39 C38 C42 120.6(5) . . ?
C38 C39 C40 122.3(5) . . ?
C39 C40 C35 118.2(5) . . ?
C39 C40 C43 120.8(5) . . ?
C35 C40 C43 121.1(5) . . ?
C45 C44 C49 120.1(4) . . ?
C45 C44 C30 120.9(4) . . ?
C49 C44 C30 119.0(4) . . ?
C46 C45 C44 118.9(5) . . ?
C46 C45 C51 119.2(5) . . ?
C44 C45 C51 121.9(4) . . ?
C47 C46 C45 122.3(5) . . ?
C46 C47 C48 118.0(5) . . ?
C46 C47 C52 120.7(6) . . ?
C48 C47 C52 121.3(6) . . ?
C47 C48 C49 122.1(5) . . ?
C48 C49 C44 118.6(5) . . ?
C48 C49 C50 119.7(5) . . ?
C44 C49 C50 121.6(5) . . ?
C9 N1 C6 105.0(4) . . ?
C19 N2 C16 110.7(4) . . ?
C26 N3 C29 105.6(4) . . ?
C34 S1 C31 92.1(2) . . ?
C1 S2 C4 91.7(2) . . ?
Cl3 C53 Cl1 98.6(10) . . ?
Cl3 C53 Cl2 115.9(11) . . ?
Cl1 C53 Cl2 108.9(11) . . ?
Cl1' C53' Cl3' 106.9(13) . . ?
Cl1' C53' Cl2' 105.2(13) . . ?
Cl3' C53' Cl2' 112.4(14) . . ?
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 C2 1.364(6) . ?
C1 C34 1.456(6) . ?
C1 S2 1.724(5) . ?
C2 C3 1.392(7) . ?
C3 C4 1.372(7) . ?
C4 C5 1.440(6) . ?
C4 S2 1.732(5) . ?
C5 C6 1.353(7) . ?
C5 C35 1.503(6) . ?
C6 N1 1.405(6) . ?
C6 C7 1.446(7) . ?
C7 C8 1.334(8) . ?
C8 C9 1.456(7) . ?
C9 N1 1.320(6) . ?
C9 C10 1.465(7) . ?
C10 C15 1.395(7) . ?
C10 C11 1.397(7) . ?
C11 C12 1.358(8) . ?
C12 C13 1.365(8) . ?
C13 C14 1.397(7) . ?
C14 C15 1.392(6) . ?
C14 C16 1.451(7) . ?
C16 C17 1.373(7) . ?
C16 N2 1.380(6) . ?
C17 C18 1.394(7) . ?
C18 C19 1.379(7) . ?
C19 N2 1.363(6) . ?
C19 C20 1.465(7) . ?
C20 C25 1.381(6) . ?
C20 C21 1.402(7) . ?
C21 C22 1.355(7) . ?
C22 C23 1.390(7) . ?
C23 C24 1.398(7) . ?
C24 C25 1.398(6) . ?
C24 C26 1.457(6) . ?
C26 N3 1.316(6) . ?
C26 C27 1.464(7) . ?
C27 C28 1.324(7) . ?
C28 C29 1.434(7) . ?
C29 C30 1.358(6) . ?
C29 N3 1.402(6) . ?
C30 C31 1.443(6) . ?
C30 C44 1.502(6) . ?
C31 C32 1.371(6) . ?
C31 S1 1.720(4) . ?
C32 C33 1.403(7) . ?
C33 C34 1.369(6) . ?
C34 S1 1.720(5) . ?
C35 C36 1.390(7) . ?
C35 C40 1.402(7) . ?
C36 C37 1.394(7) . ?
C36 C41 1.519(7) . ?
C37 C38 1.360(8) . ?
C38 C39 1.370(8) . ?
C38 C42 1.529(7) . ?
C39 C40 1.387(7) . ?
C40 C43 1.498(7) . ?
C44 C45 1.391(7) . ?
C44 C49 1.400(7) . ?
C45 C46 1.381(7) . ?
C45 C51 1.529(8) . ?
C46 C47 1.377(8) . ?
C47 C48 1.377(8) . ?
C47 C52 1.518(7) . ?
C48 C49 1.387(7) . ?
C49 C50 1.506(7) . ?
C53 Cl3 1.716(14) . ?
C53 Cl1 1.760(14) . ?
C53 Cl2 1.810(14) . ?
C53' Cl1' 1.764(15) . ?
C53' Cl3' 1.766(15) . ?
C53' Cl2' 1.782(15) . ?
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
_geom_hbond_publ_flag
C7 H7 Cl1'^b 0.95 2.76 3.49(2) 133.9 2_746 yes
C7 H7 Cl1'^b 0.95 2.76 3.49(2) 133.9 2_746 yes
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
C34 C1 C2 C3 -176.2(5) . . . . ?
S2 C1 C2 C3 1.1(6) . . . . ?
C1 C2 C3 C4 -1.1(7) . . . . ?
C2 C3 C4 C5 -176.7(5) . . . . ?
C2 C3 C4 S2 0.6(6) . . . . ?
C3 C4 C5 C6 175.9(5) . . . . ?
S2 C4 C5 C6 -1.1(7) . . . . ?
C3 C4 C5 C35 -5.8(7) . . . . ?
S2 C4 C5 C35 177.2(4) . . . . ?
C4 C5 C6 N1 4.6(8) . . . . ?
C35 C5 C6 N1 -173.7(4) . . . . ?
C4 C5 C6 C7 -176.6(5) . . . . ?
C35 C5 C6 C7 5.1(8) . . . . ?
C5 C6 C7 C8 -178.8(5) . . . . ?
N1 C6 C7 C8 0.1(7) . . . . ?
C6 C7 C8 C9 0.7(7) . . . . ?
C7 C8 C9 N1 -1.4(7) . . . . ?
C7 C8 C9 C10 175.0(5) . . . . ?
N1 C9 C10 C15 19.0(8) . . . . ?
C8 C9 C10 C15 -157.0(5) . . . . ?
N1 C9 C10 C11 -167.6(5) . . . . ?
C8 C9 C10 C11 16.4(8) . . . . ?
C15 C10 C11 C12 -1.7(8) . . . . ?
C9 C10 C11 C12 -175.3(6) . . . . ?
C10 C11 C12 C13 3.3(10) . . . . ?
C11 C12 C13 C14 -1.3(10) . . . . ?
C12 C13 C14 C15 -2.2(8) . . . . ?
C12 C13 C14 C16 175.1(5) . . . . ?
C13 C14 C15 C10 3.8(7) . . . . ?
C16 C14 C15 C10 -173.4(4) . . . . ?
C11 C10 C15 C14 -1.9(7) . . . . ?
C9 C10 C15 C14 171.5(5) . . . . ?
C15 C14 C16 C17 144.8(5) . . . . ?
C13 C14 C16 C17 -32.4(7) . . . . ?
C15 C14 C16 N2 -34.0(7) . . . . ?
C13 C14 C16 N2 148.8(5) . . . . ?
N2 C16 C17 C18 -1.6(5) . . . . ?
C14 C16 C17 C18 179.4(5) . . . . ?
C16 C17 C18 C19 0.8(6) . . . . ?
C17 C18 C19 N2 0.4(5) . . . . ?
C17 C18 C19 C20 -176.6(5) . . . . ?
N2 C19 C20 C25 30.3(7) . . . . ?
C18 C19 C20 C25 -153.2(5) . . . . ?
N2 C19 C20 C21 -152.2(5) . . . . ?
C18 C19 C20 C21 24.4(8) . . . . ?
C25 C20 C21 C22 -0.3(8) . . . . ?
C19 C20 C21 C22 -178.0(5) . . . . ?
C20 C21 C22 C23 1.0(9) . . . . ?
C21 C22 C23 C24 -0.7(9) . . . . ?
C22 C23 C24 C25 -0.4(8) . . . . ?
C22 C23 C24 C26 177.2(5) . . . . ?
C21 C20 C25 C24 -0.7(7) . . . . ?
C19 C20 C25 C24 176.8(4) . . . . ?
C23 C24 C25 C20 1.1(7) . . . . ?
C26 C24 C25 C20 -176.3(4) . . . . ?
C25 C24 C26 N3 -21.9(7) . . . . ?
C23 C24 C26 N3 160.7(5) . . . . ?
C25 C24 C26 C27 160.1(5) . . . . ?
C23 C24 C26 C27 -17.3(7) . . . . ?
N3 C26 C27 C28 -1.7(6) . . . . ?
C24 C26 C27 C28 176.6(5) . . . . ?
C26 C27 C28 C29 1.1(6) . . . . ?
C27 C28 C29 C30 -180.0(5) . . . . ?
C27 C28 C29 N3 -0.2(6) . . . . ?
N3 C29 C30 C31 8.1(8) . . . . ?
C28 C29 C30 C31 -172.2(5) . . . . ?
N3 C29 C30 C44 -175.0(4) . . . . ?
C28 C29 C30 C44 4.7(7) . . . . ?
C29 C30 C31 C32 -170.9(5) . . . . ?
C44 C30 C31 C32 12.1(7) . . . . ?
C29 C30 C31 S1 15.0(7) . . . . ?
C44 C30 C31 S1 -162.0(3) . . . . ?
C30 C31 C32 C33 -173.0(4) . . . . ?
S1 C31 C32 C33 1.8(6) . . . . ?
C31 C32 C33 C34 0.3(7) . . . . ?
C32 C33 C34 C1 171.9(5) . . . . ?
C32 C33 C34 S1 -2.3(6) . . . . ?
C2 C1 C34 C33 -24.7(8) . . . . ?
S2 C1 C34 C33 158.4(4) . . . . ?
C2 C1 C34 S1 148.9(4) . . . . ?
S2 C1 C34 S1 -28.1(6) . . . . ?
C6 C5 C35 C36 85.2(6) . . . . ?
C4 C5 C35 C36 -93.3(5) . . . . ?
C6 C5 C35 C40 -95.0(6) . . . . ?
C4 C5 C35 C40 86.6(6) . . . . ?
C40 C35 C36 C37 1.4(7) . . . . ?
C5 C35 C36 C37 -178.7(4) . . . . ?
C40 C35 C36 C41 -179.2(5) . . . . ?
C5 C35 C36 C41 0.7(7) . . . . ?
C35 C36 C37 C38 -1.4(8) . . . . ?
C41 C36 C37 C38 179.1(5) . . . . ?
C36 C37 C38 C39 1.0(9) . . . . ?
C36 C37 C38 C42 -178.5(5) . . . . ?
C37 C38 C39 C40 -0.6(9) . . . . ?
C42 C38 C39 C40 178.9(6) . . . . ?
C38 C39 C40 C35 0.6(8) . . . . ?
C38 C39 C40 C43 179.6(6) . . . . ?
C36 C35 C40 C39 -1.0(7) . . . . ?
C5 C35 C40 C39 179.2(5) . . . . ?
C36 C35 C40 C43 -180.0(5) . . . . ?
C5 C35 C40 C43 0.2(7) . . . . ?
C29 C30 C44 C45 83.3(6) . . . . ?
C31 C30 C44 C45 -99.6(5) . . . . ?
C29 C30 C44 C49 -96.1(6) . . . . ?
C31 C30 C44 C49 81.1(5) . . . . ?
C49 C44 C45 C46 -1.5(8) . . . . ?
C30 C44 C45 C46 179.1(5) . . . . ?
C49 C44 C45 C51 177.7(5) . . . . ?
C30 C44 C45 C51 -1.7(8) . . . . ?
C44 C45 C46 C47 -1.2(8) . . . . ?
C51 C45 C46 C47 179.6(6) . . . . ?
C45 C46 C47 C48 2.5(8) . . . . ?
C45 C46 C47 C52 -179.6(6) . . . . ?
C46 C47 C48 C49 -1.1(8) . . . . ?
C52 C47 C48 C49 -178.9(5) . . . . ?
C47 C48 C49 C44 -1.5(8) . . . . ?
C47 C48 C49 C50 174.9(5) . . . . ?
C45 C44 C49 C48 2.8(7) . . . . ?
C30 C44 C49 C48 -177.8(4) . . . . ?
C45 C44 C49 C50 -173.5(5) . . . . ?
C30 C44 C49 C50 5.9(7) . . . . ?
C8 C9 N1 C6 1.4(6) . . . . ?
C10 C9 N1 C6 -174.9(5) . . . . ?
C5 C6 N1 C9 178.0(5) . . . . ?
C7 C6 N1 C9 -1.0(6) . . . . ?
C18 C19 N2 C16 -1.4(5) . . . . ?
C20 C19 N2 C16 175.7(4) . . . . ?
C17 C16 N2 C19 1.9(5) . . . . ?
C14 C16 N2 C19 -179.1(4) . . . . ?
C24 C26 N3 C29 -176.8(4) . . . . ?
C27 C26 N3 C29 1.5(5) . . . . ?
C30 C29 N3 C26 178.9(5) . . . . ?
C28 C29 N3 C26 -0.8(5) . . . . ?
C33 C34 S1 C31 2.8(4) . . . . ?
C1 C34 S1 C31 -171.6(4) . . . . ?
C32 C31 S1 C34 -2.6(4) . . . . ?
C30 C31 S1 C34 172.2(4) . . . . ?
C2 C1 S2 C4 -0.6(4) . . . . ?
C34 C1 S2 C4 176.7(4) . . . . ?
C3 C4 S2 C1 0.0(4) . . . . ?
C5 C4 S2 C1 177.3(4) . . . . ?
