#------------------------------------------------------------------------------
#$Date: 2023-03-04 20:28:16 +0200 (Sat, 04 Mar 2023) $
#$Revision: 281492 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/06/21/7062122.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_7062122
loop_
_publ_author_name
'Mast, Nicolas'
'Erb, William'
'Nauton, Lionel'
'Moreau, Pascale'
'Mongin, Olivier'
'Roisnel, Thierry'
'Macaigne, Margaux'
'Robert, Thomas'
'Bach, Stéphane'
'Picot, Laurent'
'Thiéry, Valérie'
'Hurvois, Jean-Pierre'
'Mongin, Florence'
_publ_section_title
;
 From benzofuro-, benzothieno- and 10-methylindolo-[2,3-b]-fused
 benzothiopyrano[4,3,2-de]quinolines to the corresponding
 benzothiopyrano[4,3,2-de]1,8-naphthyridines: synthesis and properties of
 these hexacyclic heteroaromatic compounds
;
_journal_issue                   1
_journal_name_full               'New Journal of Chemistry'
_journal_page_first              258
_journal_page_last               283
_journal_paper_doi               10.1039/D2NJ04567B
_journal_volume                  47
_journal_year                    2023
_chemical_compound_source        'synthesis as described'
_chemical_formula_moiety         '2(C21 H11 N O3 S), C H2 Cl2'
_chemical_formula_sum            'C43 H24 Cl2 N2 O6 S2'
_chemical_formula_weight         799.66
_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
_atom_sites_solution_secondary   difmap
_audit_update_record
;
2022-09-01 deposited with the CCDC.	2022-11-28 downloaded from the CCDC.
;
_cell_angle_alpha                95.3390(10)
_cell_angle_beta                 93.9650(10)
_cell_angle_gamma                99.893(2)
_cell_formula_units_Z            2
_cell_length_a                   8.2771(3)
_cell_length_b                   13.4367(6)
_cell_length_c                   15.9360(6)
_cell_measurement_reflns_used    5485
_cell_measurement_temperature    150(2)
_cell_measurement_theta_max      27.1283
_cell_measurement_theta_min      2.5073
_cell_measurement_wavelength     0.710730
_cell_volume                     1731.86(12)
_computing_cell_refinement       'Bruker APEX2 (Bruker, 2014)'
_computing_data_collection       'Bruker APEX2 (Bruker, 2014)'
_computing_data_reduction        'Bruker APEX2 (Bruker, 2014)'
_computing_molecular_graphics
;
   'SXGRAPH (L. Farrugia, 1999), Mercury (CSD, 2020)'
;
_computing_publication_material  'CRYSCALC (T. Roisnel, local program, 2020)'
_computing_structure_refinement  'SHELXL-2018_3 (Sheldrick, 2018)'
_computing_structure_solution    'SHELXT 2018_2 (Sheldrick, 2018)'
_diffrn_ambient_temperature      150(2)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 8.33
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.983
_diffrn_measurement_device_type  'APEXII Bruker-AXS'
_diffrn_measurement_method       'CCD rotation images, thin slices'
_diffrn_orient_matrix_UB_11      0.0841156
_diffrn_orient_matrix_UB_12      0.0472093
_diffrn_orient_matrix_UB_13      0.0396975
_diffrn_orient_matrix_UB_21      0.0269212
_diffrn_orient_matrix_UB_22      0.0436842
_diffrn_orient_matrix_UB_23      -0.0464172
_diffrn_orient_matrix_UB_31      -0.0857560
_diffrn_orient_matrix_UB_32      0.0404478
_diffrn_orient_matrix_UB_33      0.0164851
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0251
_diffrn_reflns_av_unetI/netI     0.0462
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            17614
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.489
_diffrn_reflns_theta_min         2.507
_exptl_absorpt_coefficient_mu    0.365
_exptl_absorpt_correction_T_max  0.971
_exptl_absorpt_correction_T_min  0.881
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
  [Sheldrick, G.M. (2014). SADABS Bruker AXS Inc., Madison, Wisconsin, USA]
;
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.533
_exptl_crystal_description       plate
_exptl_crystal_F_000             820
_exptl_crystal_size_max          0.320
_exptl_crystal_size_mid          0.230
_exptl_crystal_size_min          0.080
_refine_diff_density_max         1.162
_refine_diff_density_min         -1.186
_refine_diff_density_rms         0.075
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.988
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     500
_refine_ls_number_reflns         7818
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.988
_refine_ls_R_factor_all          0.0885
_refine_ls_R_factor_gt           0.0591
_refine_ls_shift/su_max          0.007
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0852P)²+2.2209P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1502
_refine_ls_wR_factor_ref         0.1717
_reflns_number_gt                5578
_reflns_number_total             7818
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            d2nj04567b2.cif
_cod_data_source_block           NM013_3
_cod_depositor_comments
'Adding full bibliography for 7062120--7062126.cif.'
_cod_database_code               7062122
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
S1 S -0.00399(9) 0.74186(6) 0.87620(5) 0.02823(19) Uani 1 1 d . . . . .
C1 C 0.0469(3) 0.6456(2) 0.80769(18) 0.0250(6) Uani 1 1 d . . . . .
C2 C -0.0521(4) 0.5500(2) 0.8054(2) 0.0323(7) Uani 1 1 d . . . . .
H2 H -0.141290 0.540749 0.840033 0.039 Uiso 1 1 calc R U . . .
C3 C -0.0215(4) 0.4695(3) 0.7535(2) 0.0386(8) Uani 1 1 d . . . . .
H3 H -0.089188 0.404667 0.752588 0.046 Uiso 1 1 calc R U . . .
C4 C 0.1091(4) 0.4822(2) 0.7015(2) 0.0361(7) Uani 1 1 d . . . . .
H4 H 0.131320 0.426186 0.666102 0.043 Uiso 1 1 calc R U . . .
C5 C 0.2050(4) 0.5774(2) 0.70273(18) 0.0293(6) Uani 1 1 d . . . . .
H5 H 0.292132 0.586635 0.666840 0.035 Uiso 1 1 calc R U . . .
C6 C 0.1762(3) 0.6607(2) 0.75584(17) 0.0229(6) Uani 1 1 d . . . . .
C7 C 0.2856(3) 0.7594(2) 0.75237(17) 0.0235(6) Uani 1 1 d . . . . .
O8 O 0.3807(3) 0.76768(16) 0.69672(13) 0.0355(5) Uani 1 1 d . . . . .
C9 C 0.2812(3) 0.8458(2) 0.81747(16) 0.0198(5) Uani 1 1 d . . . . .
C10 C 0.4028(3) 0.9354(2) 0.82574(16) 0.0202(5) Uani 1 1 d . . . . .
C11 C 0.4079(3) 1.0124(2) 0.88964(17) 0.0251(6) Uani 1 1 d . . . . .
H11 H 0.492739 1.070575 0.894472 0.030 Uiso 1 1 calc R U . . .
C12 C 0.2882(4) 1.0050(2) 0.94737(18) 0.0279(6) Uani 1 1 d . . . . .
H12 H 0.292460 1.057476 0.992136 0.033 Uiso 1 1 calc R U . . .
C13 C 0.1647(3) 0.9219(2) 0.93940(17) 0.0250(6) Uani 1 1 d . . . . .
H13 H 0.081084 0.918324 0.977535 0.030 Uiso 1 1 calc R U . . .
C14 C 0.1601(3) 0.8419(2) 0.87541(17) 0.0214(5) Uani 1 1 d . . . . .
N25 N 0.5276(3) 0.94848(17) 0.76813(13) 0.0213(5) Uani 1 1 d . . . . .
C26 C 0.6888(3) 0.9345(2) 0.78749(17) 0.0217(5) Uani 1 1 d . . . . .
C27 C 0.7659(3) 0.9351(2) 0.70590(17) 0.0211(5) Uani 1 1 d . . . . .
C28 C 0.9225(3) 0.9206(2) 0.68875(18) 0.0256(6) Uani 1 1 d . . . . .
H28 H 1.001862 0.912806 0.732491 0.031 Uiso 1 1 calc R U . . .
C29 C 0.9584(3) 0.9179(2) 0.60462(19) 0.0293(6) Uani 1 1 d . . . . .
H29 H 1.064375 0.907822 0.590358 0.035 Uiso 1 1 calc R U . . .
C30 C 0.8415(3) 0.9299(2) 0.54111(18) 0.0280(6) Uani 1 1 d . . . . .
H30 H 0.868720 0.926373 0.484096 0.034 Uiso 1 1 calc R U . . .
C31 C 0.6861(3) 0.9467(2) 0.55900(17) 0.0255(6) Uani 1 1 d . . . . .
H31 H 0.607386 0.956523 0.515700 0.031 Uiso 1 1 calc R U . . .
C32 C 0.6509(3) 0.9486(2) 0.64274(17) 0.0213(5) Uani 1 1 d . . . . .
C33 C 0.4961(3) 0.9599(2) 0.68159(17) 0.0227(6) Uani 1 1 d . . . . .
O34 O 0.7484(2) 0.92367(16) 0.85660(12) 0.0287(5) Uani 1 1 d . . . . .
O35 O 0.3697(2) 0.97880(16) 0.65040(12) 0.0297(5) Uani 1 1 d . . . . .
S2 S 0.84335(9) 0.57459(6) 0.03519(5) 0.02879(19) Uani 1 1 d . . . . .
C51 C 0.6935(3) 0.4730(2) 0.05396(18) 0.0246(6) Uani 1 1 d . . . . .
C52 C 0.6896(4) 0.3823(2) 0.00307(19) 0.0304(6) Uani 1 1 d . . . . .
H52 H 0.763404 0.379201 -0.039804 0.036 Uiso 1 1 calc R U . . .
C53 C 0.5785(4) 0.2970(2) 0.0152(2) 0.0331(7) Uani 1 1 d . . . . .
H53 H 0.575302 0.235321 -0.019732 0.040 Uiso 1 1 calc R U . . .
C54 C 0.4706(4) 0.3009(2) 0.0786(2) 0.0315(7) Uani 1 1 d . . . . .
H54 H 0.396030 0.241656 0.087819 0.038 Uiso 1 1 calc R U . . .
C55 C 0.4729(3) 0.3912(2) 0.12745(19) 0.0274(6) Uani 1 1 d . . . . .
H55 H 0.398544 0.393512 0.170094 0.033 Uiso 1 1 calc R U . . .
C56 C 0.5823(3) 0.4797(2) 0.11591(18) 0.0246(6) Uani 1 1 d . . . . .
C57 C 0.5685(3) 0.5747(2) 0.1681(2) 0.0289(6) Uani 1 1 d . . . . .
O58 O 0.4557(3) 0.57378(17) 0.21387(18) 0.0503(7) Uani 1 1 d . . . . .
C59 C 0.6910(3) 0.6690(2) 0.16379(18) 0.0238(6) Uani 1 1 d . . . . .
C60 C 0.6891(3) 0.7590(2) 0.21733(18) 0.0231(6) Uani 1 1 d . . . . .
C61 C 0.8055(3) 0.8455(2) 0.21696(18) 0.0268(6) Uani 1 1 d . . . . .
H61 H 0.800748 0.904554 0.253700 0.032 Uiso 1 1 calc R U . . .
C62 C 0.9304(3) 0.8461(2) 0.16253(19) 0.0279(6) Uani 1 1 d . . . . .
H62 H 1.011423 0.905469 0.162605 0.034 Uiso 1 1 calc R U . . .
C63 C 0.9367(3) 0.7614(2) 0.10907(18) 0.0259(6) Uani 1 1 d . . . . .
H63 H 1.022006 0.762011 0.072077 0.031 Uiso 1 1 calc R U . . .
C64 C 0.8167(3) 0.6733(2) 0.10885(17) 0.0233(6) Uani 1 1 d . . . . .
N65 N 0.5679(3) 0.76429(18) 0.27664(15) 0.0241(5) Uani 1 1 d . . . . .
C66 C 0.4062(3) 0.7767(2) 0.25644(19) 0.0256(6) Uani 1 1 d . . . . .
C67 C 0.3245(3) 0.7704(2) 0.33653(18) 0.0235(6) Uani 1 1 d . . . . .
C68 C 0.1651(3) 0.7775(2) 0.35301(19) 0.0283(6) Uani 1 1 d . . . . .
H68 H 0.087897 0.789901 0.310018 0.034 Uiso 1 1 calc R U . . .
C69 C 0.1215(4) 0.7660(2) 0.4347(2) 0.0328(7) Uani 1 1 d . . . . .
H69 H 0.012472 0.770133 0.447881 0.039 Uiso 1 1 calc R U . . .
C70 C 0.2354(4) 0.7485(3) 0.4973(2) 0.0377(8) Uani 1 1 d . . . . .
H70 H 0.202852 0.741151 0.552703 0.045 Uiso 1 1 calc R U . . .
C71 C 0.3959(4) 0.7415(3) 0.48071(19) 0.0355(7) Uani 1 1 d . . . . .
H71 H 0.473840 0.729718 0.523617 0.043 Uiso 1 1 calc R U . . .
C72 C 0.4372(3) 0.7523(2) 0.39923(18) 0.0264(6) Uani 1 1 d . . . . .
C73 C 0.5948(3) 0.7461(2) 0.36123(19) 0.0281(6) Uani 1 1 d . . . . .
O74 O 0.3499(3) 0.79064(18) 0.18718(14) 0.0364(5) Uani 1 1 d . . . . .
O75 O 0.7226(3) 0.7299(2) 0.39304(14) 0.0427(6) Uani 1 1 d . . . . .
C101 C 0.6792(9) 0.5369(6) 0.6029(5) 0.0628(16) Uani 0.609(6) 1 d . . P A 1
H10A H 0.711278 0.494268 0.646452 0.075 Uiso 0.609(6) 1 calc R U P A 1
H10B H 0.562596 0.510029 0.582952 0.075 Uiso 0.609(6) 1 calc R U P A 1
Cl1A Cl 0.7879(4) 0.52234(18) 0.52485(12) 0.1545(10) Uani 0.609(6) 1 d . . P A 1
Cl2A Cl 0.69158(17) 0.66153(9) 0.65226(7) 0.0720(4) Uani 0.609(6) 1 d . . P A 1
C111 C 0.8156(14) 0.6251(9) 0.5821(7) 0.0628(16) Uani 0.391(6) 1 d . . P A 2
H11A H 0.829416 0.678505 0.543023 0.075 Uiso 0.391(6) 1 calc R U P A 2
H11B H 0.924130 0.630301 0.614084 0.075 Uiso 0.391(6) 1 calc R U P A 2
Cl1B Cl 0.7879(4) 0.52234(18) 0.52485(12) 0.1545(10) Uani 0.391(6) 1 d . . P A 2
Cl2B Cl 0.69158(17) 0.66153(9) 0.65226(7) 0.0720(4) Uani 0.391(6) 1 d . . 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'
O O 0.0106 0.0060 '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
C14 S1 C1 103.55(13) . . ?
C6 C1 C2 120.4(3) . . ?
C6 C1 S1 123.5(2) . . ?
C2 C1 S1 116.2(2) . . ?
C3 C2 C1 120.4(3) . . ?
C3 C2 H2 119.8 . . ?
C1 C2 H2 119.8 . . ?
C2 C3 C4 120.5(3) . . ?
C2 C3 H3 119.8 . . ?
C4 C3 H3 119.8 . . ?
C5 C4 C3 119.0(3) . . ?
C5 C4 H4 120.5 . . ?
C3 C4 H4 120.5 . . ?
C4 C5 C6 121.4(3) . . ?
C4 C5 H5 119.3 . . ?
C6 C5 H5 119.3 . . ?
C1 C6 C5 118.4(3) . . ?
C1 C6 C7 124.4(2) . . ?
C5 C6 C7 117.2(2) . . ?
O8 C7 C6 119.0(2) . . ?
O8 C7 C9 121.3(3) . . ?
C6 C7 C9 119.6(2) . . ?
C14 C9 C10 116.5(2) . . ?
C14 C9 C7 122.0(2) . . ?
C10 C9 C7 121.4(2) . . ?
C11 C10 C9 122.1(2) . . ?
C11 C10 N25 117.0(2) . . ?
C9 C10 N25 120.9(2) . . ?
C10 C11 C12 119.9(3) . . ?
C10 C11 H11 120.1 . . ?
C12 C11 H11 120.1 . . ?
C13 C12 C11 119.9(3) . . ?
C13 C12 H12 120.0 . . ?
C11 C12 H12 120.0 . . ?
C12 C13 C14 120.7(2) . . ?
C12 C13 H13 119.6 . . ?
C14 C13 H13 119.6 . . ?
C13 C14 C9 120.8(2) . . ?
C13 C14 S1 114.21(19) . . ?
C9 C14 S1 125.0(2) . . ?
C26 N25 C33 112.1(2) . . ?
C26 N25 C10 123.4(2) . . ?
C33 N25 C10 123.8(2) . . ?
O34 C26 N25 125.8(2) . . ?
O34 C26 C27 128.9(2) . . ?
N25 C26 C27 105.4(2) . . ?
C32 C27 C28 121.7(2) . . ?
C32 C27 C26 108.9(2) . . ?
C28 C27 C26 129.3(3) . . ?
C27 C28 C29 117.1(3) . . ?
C27 C28 H28 121.5 . . ?
C29 C28 H28 121.5 . . ?
C30 C29 C28 121.0(3) . . ?
C30 C29 H29 119.5 . . ?
C28 C29 H29 119.5 . . ?
C31 C30 C29 121.6(3) . . ?
C31 C30 H30 119.2 . . ?
C29 C30 H30 119.2 . . ?
C32 C31 C30 117.0(3) . . ?
C32 C31 H31 121.5 . . ?
C30 C31 H31 121.5 . . ?
C27 C32 C31 121.5(2) . . ?
C27 C32 C33 108.3(2) . . ?
C31 C32 C33 130.2(3) . . ?
O35 C33 N25 124.7(2) . . ?
O35 C33 C32 129.9(2) . . ?
N25 C33 C32 105.3(2) . . ?
C64 S2 C51 104.04(13) . . ?
C52 C51 C56 120.9(3) . . ?
C52 C51 S2 115.8(2) . . ?
C56 C51 S2 123.4(2) . . ?
C53 C52 C51 119.8(3) . . ?
C53 C52 H52 120.1 . . ?
C51 C52 H52 120.1 . . ?
C52 C53 C54 120.3(3) . . ?
C52 C53 H53 119.8 . . ?
C54 C53 H53 119.8 . . ?
C55 C54 C53 119.6(3) . . ?
C55 C54 H54 120.2 . . ?
C53 C54 H54 120.2 . . ?
C54 C55 C56 121.6(3) . . ?
C54 C55 H55 119.2 . . ?
C56 C55 H55 119.2 . . ?
C55 C56 C51 117.8(3) . . ?
C55 C56 C57 117.6(2) . . ?
C51 C56 C57 124.6(3) . . ?
O58 C57 C56 118.9(3) . . ?
O58 C57 C59 121.3(3) . . ?
C56 C57 C59 119.8(2) . . ?
C64 C59 C60 116.3(2) . . ?
C64 C59 C57 122.4(3) . . ?
C60 C59 C57 121.3(2) . . ?
C61 C60 C59 122.2(2) . . ?
C61 C60 N65 116.1(2) . . ?
C59 C60 N65 121.7(2) . . ?
C60 C61 C62 119.8(3) . . ?
C60 C61 H61 120.1 . . ?
C62 C61 H61 120.1 . . ?
C63 C62 C61 120.2(3) . . ?
C63 C62 H62 119.9 . . ?
C61 C62 H62 119.9 . . ?
C62 C63 C64 120.0(2) . . ?
C62 C63 H63 120.0 . . ?
C64 C63 H63 120.0 . . ?
C59 C64 C63 121.5(3) . . ?
C59 C64 S2 125.3(2) . . ?
C63 C64 S2 113.1(2) . . ?
C66 N65 C73 112.0(2) . . ?
C66 N65 C60 125.1(2) . . ?
C73 N65 C60 122.6(2) . . ?
O74 C66 N65 125.2(3) . . ?
O74 C66 C67 129.1(2) . . ?
N65 C66 C67 105.7(2) . . ?
C68 C67 C72 121.2(3) . . ?
C68 C67 C66 130.4(3) . . ?
C72 C67 C66 108.4(2) . . ?
C67 C68 C69 117.7(3) . . ?
C67 C68 H68 121.2 . . ?
C69 C68 H68 121.2 . . ?
C70 C69 C68 120.8(3) . . ?
C70 C69 H69 119.6 . . ?
C68 C69 H69 119.6 . . ?
C69 C70 C71 121.5(3) . . ?
C69 C70 H70 119.2 . . ?
C71 C70 H70 119.2 . . ?
C72 C71 C70 117.1(3) . . ?
C72 C71 H71 121.5 . . ?
C70 C71 H71 121.5 . . ?
C71 C72 C67 121.7(3) . . ?
C71 C72 C73 130.1(3) . . ?
C67 C72 C73 108.2(2) . . ?
O75 C73 N65 124.5(3) . . ?
O75 C73 C72 129.8(3) . . ?
N65 C73 C72 105.7(2) . . ?
Cl1A C101 Cl2A 117.4(4) . . ?
Cl1A C101 H10A 108.0 . . ?
Cl2A C101 H10A 108.0 . . ?
Cl1A C101 H10B 108.0 . . ?
Cl2A C101 H10B 108.0 . . ?
H10A C101 H10B 107.2 . . ?
Cl1B C111 Cl2B 126.6(7) . . ?
Cl1B C111 H11A 105.7 . . ?
Cl2B C111 H11A 105.7 . . ?
Cl1B C111 H11B 105.7 . . ?
Cl2B C111 H11B 105.6 . . ?
H11A C111 H11B 106.1 . . ?
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
S1 C14 1.740(3) . ?
S1 C1 1.741(3) . ?
C1 C6 1.396(4) . ?
C1 C2 1.396(4) . ?
C2 C3 1.369(4) . ?
C2 H2 0.9500 . ?
C3 C4 1.403(5) . ?
C3 H3 0.9500 . ?
C4 C5 1.382(4) . ?
C4 H4 0.9500 . ?
C5 C6 1.403(4) . ?
C5 H5 0.9500 . ?
C6 C7 1.480(4) . ?
C7 O8 1.226(3) . ?
C7 C9 1.490(4) . ?
C9 C14 1.407(3) . ?
C9 C10 1.420(4) . ?
C10 C11 1.375(4) . ?
C10 N25 1.428(3) . ?
C11 C12 1.395(4) . ?
C11 H11 0.9500 . ?
C12 C13 1.367(4) . ?
C12 H12 0.9500 . ?
C13 C14 1.405(4) . ?
C13 H13 0.9500 . ?
N25 C26 1.397(3) . ?
N25 C33 1.413(3) . ?
C26 O34 1.207(3) . ?
C26 C27 1.488(4) . ?
C27 C32 1.383(4) . ?
C27 C28 1.385(4) . ?
C28 C29 1.392(4) . ?
C28 H28 0.9500 . ?
C29 C30 1.390(4) . ?
C29 H29 0.9500 . ?
C30 C31 1.388(4) . ?
C30 H30 0.9500 . ?
C31 C32 1.384(4) . ?
C31 H31 0.9500 . ?
C32 C33 1.486(3) . ?
C33 O35 1.203(3) . ?
S2 C64 1.741(3) . ?
S2 C51 1.742(3) . ?
C51 C52 1.395(4) . ?
C51 C56 1.402(4) . ?
C52 C53 1.378(4) . ?
C52 H52 0.9500 . ?
C53 C54 1.397(4) . ?
C53 H53 0.9500 . ?
C54 C55 1.375(4) . ?
C54 H54 0.9500 . ?
C55 C56 1.401(4) . ?
C55 H55 0.9500 . ?
C56 C57 1.483(4) . ?
C57 O58 1.224(3) . ?
C57 C59 1.491(4) . ?
C59 C64 1.403(4) . ?
C59 C60 1.416(4) . ?
C60 C61 1.377(4) . ?
C60 N65 1.431(3) . ?
C61 C62 1.394(4) . ?
C61 H61 0.9500 . ?
C62 C63 1.367(4) . ?
C62 H62 0.9500 . ?
C63 C64 1.408(4) . ?
C63 H63 0.9500 . ?
N65 C66 1.397(3) . ?
N65 C73 1.402(4) . ?
C66 O74 1.211(4) . ?
C66 C67 1.488(4) . ?
C67 C68 1.380(4) . ?
C67 C72 1.387(4) . ?
C68 C69 1.390(4) . ?
C68 H68 0.9500 . ?
C69 C70 1.389(4) . ?
C69 H69 0.9500 . ?
C70 C71 1.389(4) . ?
C70 H70 0.9500 . ?
C71 C72 1.380(4) . ?
C71 H71 0.9500 . ?
C72 C73 1.488(4) . ?
C73 O75 1.204(3) . ?
C101 Cl1A 1.602(8) . ?
C101 Cl2A 1.766(8) . ?
C101 H10A 0.9900 . ?
C101 H10B 0.9900 . ?
C111 Cl1B 1.555(12) . ?
C111 Cl2B 1.665(12) . ?
C111 H11A 0.9900 . ?
C111 H11B 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
C14 S1 C1 C6 -10.3(3) . . . . ?
C14 S1 C1 C2 170.9(2) . . . . ?
C6 C1 C2 C3 1.3(5) . . . . ?
S1 C1 C2 C3 -179.9(2) . . . . ?
C1 C2 C3 C4 -0.4(5) . . . . ?
C2 C3 C4 C5 -0.9(5) . . . . ?
C3 C4 C5 C6 1.3(5) . . . . ?
C2 C1 C6 C5 -0.9(4) . . . . ?
S1 C1 C6 C5 -179.6(2) . . . . ?
C2 C1 C6 C7 178.6(3) . . . . ?
S1 C1 C6 C7 0.0(4) . . . . ?
C4 C5 C6 C1 -0.4(4) . . . . ?
C4 C5 C6 C7 -180.0(3) . . . . ?
C1 C6 C7 O8 -170.2(3) . . . . ?
C5 C6 C7 O8 9.4(4) . . . . ?
C1 C6 C7 C9 11.3(4) . . . . ?
C5 C6 C7 C9 -169.1(2) . . . . ?
O8 C7 C9 C14 172.2(3) . . . . ?
C6 C7 C9 C14 -9.3(4) . . . . ?
O8 C7 C9 C10 -9.8(4) . . . . ?
C6 C7 C9 C10 168.7(2) . . . . ?
C14 C9 C10 C11 3.4(4) . . . . ?
C7 C9 C10 C11 -174.8(2) . . . . ?
C14 C9 C10 N25 -177.7(2) . . . . ?
C7 C9 C10 N25 4.1(4) . . . . ?
C9 C10 C11 C12 -1.9(4) . . . . ?
N25 C10 C11 C12 179.2(2) . . . . ?
C10 C11 C12 C13 -1.1(4) . . . . ?
C11 C12 C13 C14 2.4(4) . . . . ?
C12 C13 C14 C9 -0.8(4) . . . . ?
C12 C13 C14 S1 179.0(2) . . . . ?
C10 C9 C14 C13 -2.0(4) . . . . ?
C7 C9 C14 C13 176.1(2) . . . . ?
C10 C9 C14 S1 178.3(2) . . . . ?
C7 C9 C14 S1 -3.6(4) . . . . ?
C1 S1 C14 C13 -167.5(2) . . . . ?
C1 S1 C14 C9 12.2(3) . . . . ?
C11 C10 N25 C26 77.3(3) . . . . ?
C9 C10 N25 C26 -101.7(3) . . . . ?
C11 C10 N25 C33 -113.8(3) . . . . ?
C9 C10 N25 C33 67.3(4) . . . . ?
C33 N25 C26 O34 179.3(3) . . . . ?
C10 N25 C26 O34 -10.6(4) . . . . ?
C33 N25 C26 C27 -1.1(3) . . . . ?
C10 N25 C26 C27 169.0(2) . . . . ?
O34 C26 C27 C32 179.2(3) . . . . ?
N25 C26 C27 C32 -0.3(3) . . . . ?
O34 C26 C27 C28 2.1(5) . . . . ?
N25 C26 C27 C28 -177.4(3) . . . . ?
C32 C27 C28 C29 -1.3(4) . . . . ?
C26 C27 C28 C29 175.4(3) . . . . ?
C27 C28 C29 C30 0.3(4) . . . . ?
C28 C29 C30 C31 1.2(5) . . . . ?
C29 C30 C31 C32 -1.6(4) . . . . ?
C28 C27 C32 C31 0.9(4) . . . . ?
C26 C27 C32 C31 -176.4(3) . . . . ?
C28 C27 C32 C33 178.8(3) . . . . ?
C26 C27 C32 C33 1.5(3) . . . . ?
C30 C31 C32 C27 0.5(4) . . . . ?
C30 C31 C32 C33 -176.9(3) . . . . ?
C26 N25 C33 O35 -175.4(3) . . . . ?
C10 N25 C33 O35 14.5(4) . . . . ?
C26 N25 C33 C32 2.0(3) . . . . ?
C10 N25 C33 C32 -168.1(2) . . . . ?
C27 C32 C33 O35 175.1(3) . . . . ?
C31 C32 C33 O35 -7.2(5) . . . . ?
C27 C32 C33 N25 -2.1(3) . . . . ?
C31 C32 C33 N25 175.6(3) . . . . ?
C64 S2 C51 C52 -179.2(2) . . . . ?
C64 S2 C51 C56 0.7(3) . . . . ?
C56 C51 C52 C53 -1.9(4) . . . . ?
S2 C51 C52 C53 178.0(2) . . . . ?
C51 C52 C53 C54 -0.5(5) . . . . ?
C52 C53 C54 C55 1.7(5) . . . . ?
C53 C54 C55 C56 -0.6(4) . . . . ?
C54 C55 C56 C51 -1.7(4) . . . . ?
C54 C55 C56 C57 176.3(3) . . . . ?
C52 C51 C56 C55 2.9(4) . . . . ?
S2 C51 C56 C55 -177.0(2) . . . . ?
C52 C51 C56 C57 -174.9(3) . . . . ?
S2 C51 C56 C57 5.2(4) . . . . ?
C55 C56 C57 O58 -5.4(4) . . . . ?
C51 C56 C57 O58 172.4(3) . . . . ?
C55 C56 C57 C59 174.7(3) . . . . ?
C51 C56 C57 C59 -7.5(4) . . . . ?
O58 C57 C59 C64 -176.9(3) . . . . ?
C56 C57 C59 C64 2.9(4) . . . . ?
O58 C57 C59 C60 5.0(5) . . . . ?
C56 C57 C59 C60 -175.2(3) . . . . ?
C64 C59 C60 C61 -1.2(4) . . . . ?
C57 C59 C60 C61 177.0(3) . . . . ?
C64 C59 C60 N65 -179.5(2) . . . . ?
C57 C59 C60 N65 -1.3(4) . . . . ?
C59 C60 C61 C62 0.0(4) . . . . ?
N65 C60 C61 C62 178.5(3) . . . . ?
C60 C61 C62 C63 0.6(4) . . . . ?
C61 C62 C63 C64 0.0(4) . . . . ?
C60 C59 C64 C63 1.8(4) . . . . ?
C57 C59 C64 C63 -176.4(3) . . . . ?
C60 C59 C64 S2 -178.4(2) . . . . ?
C57 C59 C64 S2 3.4(4) . . . . ?
C62 C63 C64 C59 -1.3(4) . . . . ?
C62 C63 C64 S2 178.9(2) . . . . ?
C51 S2 C64 C59 -4.9(3) . . . . ?
C51 S2 C64 C63 174.9(2) . . . . ?
C61 C60 N65 C66 102.8(3) . . . . ?
C59 C60 N65 C66 -78.7(4) . . . . ?
C61 C60 N65 C73 -84.5(3) . . . . ?
C59 C60 N65 C73 94.0(3) . . . . ?
C73 N65 C66 O74 -178.1(3) . . . . ?
C60 N65 C66 O74 -4.7(5) . . . . ?
C73 N65 C66 C67 2.7(3) . . . . ?
C60 N65 C66 C67 176.1(2) . . . . ?
O74 C66 C67 C68 0.9(5) . . . . ?
N65 C66 C67 C68 -180.0(3) . . . . ?
O74 C66 C67 C72 179.3(3) . . . . ?
N65 C66 C67 C72 -1.5(3) . . . . ?
C72 C67 C68 C69 0.1(4) . . . . ?
C66 C67 C68 C69 178.3(3) . . . . ?
C67 C68 C69 C70 0.3(5) . . . . ?
C68 C69 C70 C71 -0.3(5) . . . . ?
C69 C70 C71 C72 -0.2(5) . . . . ?
C70 C71 C72 C67 0.6(5) . . . . ?
C70 C71 C72 C73 -178.2(3) . . . . ?
C68 C67 C72 C71 -0.6(5) . . . . ?
C66 C67 C72 C71 -179.2(3) . . . . ?
C68 C67 C72 C73 178.5(3) . . . . ?
C66 C67 C72 C73 -0.1(3) . . . . ?
C66 N65 C73 O75 177.6(3) . . . . ?
C60 N65 C73 O75 4.1(5) . . . . ?
C66 N65 C73 C72 -2.8(3) . . . . ?
C60 N65 C73 C72 -176.3(2) . . . . ?
C71 C72 C73 O75 0.2(6) . . . . ?
C67 C72 C73 O75 -178.7(3) . . . . ?
C71 C72 C73 N65 -179.3(3) . . . . ?
C67 C72 C73 N65 1.7(3) . . . . ?
