#------------------------------------------------------------------------------
#$Date: 2021-06-05 22:26:55 +0300 (Sat, 05 Jun 2021) $
#$Revision: 266156 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/15/79/7157994.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_7157994
loop_
_publ_author_name
'Wei, Yueting'
'Liu, Ping'
'Liu, Yali'
'He, Jing'
'Li, Xuezhen'
'Li, Shiwu'
'Zhao, Jixing'
_publ_section_title
;
 NIS-promoted three-component reaction of 3-oxo-3-arylpropanenitriles with
 arylsulfonyl hydrazides.
;
_journal_issue                   17
_journal_name_full               'Organic & biomolecular chemistry'
_journal_page_first              3932
_journal_page_last               3939
_journal_paper_doi               10.1039/d1ob00438g
_journal_volume                  19
_journal_year                    2021
_chemical_formula_moiety         'C H Cl3, 3(C16 H12 F3 N3 S)'
_chemical_formula_sum            'C49 H37 Cl3 F9 N9 S3'
_chemical_formula_weight         1125.40
_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   mixed
_atom_sites_solution_primary     dual
_audit_creation_date             2020-08-10
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_audit_update_record
;
2020-10-05 deposited with the CCDC.	2021-03-29 downloaded from the CCDC.
;
_cell_angle_alpha                106.397(2)
_cell_angle_beta                 108.593(2)
_cell_angle_gamma                108.531(2)
_cell_formula_units_Z            2
_cell_length_a                   13.8799(8)
_cell_length_b                   14.9130(8)
_cell_length_c                   14.9991(7)
_cell_measurement_reflns_used    9830
_cell_measurement_temperature    173(2)
_cell_measurement_theta_max      26.72
_cell_measurement_theta_min      2.68
_cell_volume                     2523.1(2)
_computing_cell_refinement       'SAINT V8.38A (?, 2016)'
_computing_data_reduction        'SAINT V8.38A (?, 2016)'
_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      173.0
_diffrn_detector_area_resol_mean 8
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measurement_device_type  'Bruker D8 Venture'
_diffrn_measurement_method       'ω and φ scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0348
_diffrn_reflns_av_unetI/netI     0.0387
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.995
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_h_min       -17
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            32090
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.995
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.766
_diffrn_reflns_theta_min         2.294
_diffrn_source                   'sealed tube'
_exptl_absorpt_coefficient_mu    0.385
_exptl_absorpt_correction_T_max  0.7454
_exptl_absorpt_correction_T_min  0.6331
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   SADABS
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.481
_exptl_crystal_description       block
_exptl_crystal_F_000             1148
_exptl_crystal_size_max          0.22
_exptl_crystal_size_mid          0.21
_exptl_crystal_size_min          0.19
_refine_diff_density_max         0.931
_refine_diff_density_min         -0.729
_refine_diff_density_rms         0.081
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.106
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     719
_refine_ls_number_reflns         10688
_refine_ls_number_restraints     219
_refine_ls_restrained_S_all      1.169
_refine_ls_R_factor_all          0.0850
_refine_ls_R_factor_gt           0.0712
_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)+(0.0571P)²+6.9390P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1744
_refine_ls_wR_factor_ref         0.1828
_reflns_Friedel_coverage         0.000
_reflns_number_gt                8785
_reflns_number_total             10688
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d1ob00438g1.cif
_cod_data_source_block           11_CCDC1
_cod_depositor_comments
'Adding full bibliography for 7157992--7157994.cif.'
_cod_database_code               7157994
_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_max   0.930
_shelx_estimated_absorpt_t_min   0.920
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All N(H) groups
2. Restrained distances
 C49A-Cl3A \\sim C49-Cl3
 with sigma of 0.02
 Cl1A-C49A \\sim Cl1-C49
 with sigma of 0.02
 Cl1A-Cl3A \\sim Cl1-Cl3
 with sigma of 0.02
3. Uiso/Uaniso restraints and constraints
Cl1 \\sim Cl1A \\sim Cl2 \\sim Cl2A \\sim Cl3 \\sim Cl3A \\sim C49 \\sim C49A:
within 3.8A with sigma of 0.01 and sigma for terminal atoms of 0.02
Uanis(F2) \\sim Ueq, Uanis(F6) \\sim Ueq, Uanis(F8) \\sim Ueq: with sigma of
0.002 and sigma for terminal atoms of 0.004
4. Rigid body (RIGU) restrains
 Cl1, Cl2, Cl3, C49
 with sigma for 1-2 distances of 0.004 and sigma for 1-3 distances of 0.004
 Cl1A, Cl2A, Cl3A, C49A
 with sigma for 1-2 distances of 0.004 and sigma for 1-3 distances of 0.004
5. Others
 Sof(Cl1A)=Sof(Cl2A)=Sof(Cl3A)=Sof(C49A)=Sof(H49A)=1-FVAR(1)
 Sof(Cl1)=Sof(Cl2)=Sof(Cl3)=Sof(C49)=Sof(H49)=FVAR(1)
6.a Ternary CH refined with riding coordinates:
 C49(H49), C49A(H49A)
6.b Aromatic/amide H refined with riding coordinates:
 N5(H5), C21(H21), C22(H22), C23(H23), C24(H24), C25(H25), C27(H27), C28(H28),
 C30(H30), C31(H31), N8(H8), C37(H37), C38(H38), C39(H39), C40(H40), C41(H41),
 C43(H43), C44(H44), C46(H46), C47(H47), N2(H2), C5(H5A), C6(H6), C7(H7),
 C8(H8A), C9(H9), C11(H11), C12(H12), C14(H14), C15(H15)
;
_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 0.25809(16) 0.38373(14) 0.35658(15) 0.0641(6) Uani 0.836(4) 1 d D U P A
1
Cl1A Cl 0.3673(12) 0.4535(8) 0.4383(9) 0.092(3) Uani 0.164(4) 1 d D U P A 2
Cl2 Cl 0.4005(3) 0.3645(2) 0.25662(18) 0.0535(6) Uani 0.836(4) 1 d . U P A 1
Cl2A Cl 0.4249(13) 0.3924(13) 0.2881(13) 0.061(3) Uani 0.164(4) 1 d . U P A 2
Cl3 Cl 0.3757(2) 0.25861(18) 0.3890(2) 0.0530(6) Uani 0.836(4) 1 d D U P A 1
Cl3A Cl 0.4135(13) 0.2851(12) 0.4113(15) 0.071(3) Uani 0.164(4) 1 d D U P A 2
C49 C 0.3167(6) 0.3076(6) 0.3058(6) 0.0505(14) Uani 0.836(4) 1 d D U P A 1
H49 H 0.250361 0.244742 0.244127 0.061 Uiso 0.836(4) 1 calc R . P A 1
C49A C 0.330(3) 0.333(2) 0.348(2) 0.061(5) Uani 0.164(4) 1 d D U P A 2
H49A H 0.247809 0.284894 0.300695 0.074 Uiso 0.164(4) 1 calc R . P A 2
S2 S 0.88040(8) 0.54748(6) 0.99853(7) 0.0275(2) Uani 1 1 d . . . . .
F4 F 0.4159(3) 0.1713(3) 0.5758(3) 0.0884(12) Uani 1 1 d . . . . .
F5 F 0.5347(4) 0.1603(3) 0.5229(3) 0.0963(13) Uani 1 1 d . . . . .
F6 F 0.4975(3) 0.0792(2) 0.6120(3) 0.0908(12) Uani 1 1 d . U . . .
N4 N 0.7378(3) 0.6831(3) 1.0146(3) 0.0365(8) Uani 1 1 d . . . . .
N5 N 0.8647(2) 0.7952(2) 0.9742(2) 0.0262(6) Uani 1 1 d . . . . .
H5 H 0.837998 0.841663 0.980257 0.031 Uiso 1 1 calc R . . . .
N6 N 0.9530(2) 0.8021(2) 0.9496(2) 0.0258(6) Uani 1 1 d . . . . .
C17 C 0.8243(3) 0.7084(3) 0.9879(3) 0.0250(7) Uani 1 1 d . . . . .
C18 C 0.8883(3) 0.6551(3) 0.9722(3) 0.0244(7) Uani 1 1 d . . . . .
C19 C 0.9673(3) 0.7169(3) 0.9475(2) 0.0228(7) Uani 1 1 d . . . . .
C20 C 1.0547(3) 0.7007(3) 0.9194(2) 0.0240(7) Uani 1 1 d . . . . .
C21 C 1.0369(3) 0.6016(3) 0.8596(3) 0.0282(7) Uani 1 1 d . . . . .
H21 H 0.968752 0.542251 0.839307 0.034 Uiso 1 1 calc R . . . .
C22 C 1.1181(3) 0.5886(3) 0.8291(3) 0.0355(9) Uani 1 1 d . . . . .
H22 H 1.105468 0.520402 0.788932 0.043 Uiso 1 1 calc R . . . .
C23 C 1.2167(3) 0.6741(3) 0.8568(3) 0.0377(9) Uani 1 1 d . . . . .
H23 H 1.271023 0.665023 0.834357 0.045 Uiso 1 1 calc R . . . .
C24 C 1.2360(3) 0.7729(3) 0.9175(3) 0.0369(9) Uani 1 1 d . . . . .
H24 H 1.304666 0.831754 0.937940 0.044 Uiso 1 1 calc R . . . .
C25 C 1.1565(3) 0.7868(3) 0.9485(3) 0.0300(8) Uani 1 1 d . . . . .
H25 H 1.170677 0.855227 0.990003 0.036 Uiso 1 1 calc R . . . .
C26 C 0.7728(3) 0.4387(3) 0.8808(3) 0.0256(7) Uani 1 1 d . . . . .
C27 C 0.7209(3) 0.4475(3) 0.7905(3) 0.0356(9) Uani 1 1 d . . . . .
H27 H 0.742475 0.514386 0.789751 0.043 Uiso 1 1 calc R . . . .
C28 C 0.6376(4) 0.3593(3) 0.7011(3) 0.0427(10) Uani 1 1 d . . . . .
H28 H 0.602286 0.365465 0.639035 0.051 Uiso 1 1 calc R . . . .
C29 C 0.6058(3) 0.2616(3) 0.7023(3) 0.0343(8) Uani 1 1 d . . . . .
C30 C 0.6572(3) 0.2526(3) 0.7914(3) 0.0356(9) Uani 1 1 d . . . . .
H30 H 0.635439 0.185794 0.792284 0.043 Uiso 1 1 calc R . . . .
C31 C 0.7415(3) 0.3414(3) 0.8808(3) 0.0311(8) Uani 1 1 d . . . . .
H31 H 0.777712 0.334934 0.942398 0.037 Uiso 1 1 calc R . . . .
C32 C 0.5149(4) 0.1682(3) 0.6052(4) 0.0493(12) Uani 1 1 d . . . . .
S3 S 0.47871(8) 0.95146(7) 0.85066(7) 0.0328(2) Uani 1 1 d . . . . .
F7 F 0.1575(3) 0.5671(3) 0.3766(2) 0.1007(15) Uani 1 1 d . . . . .
F8 F 0.0258(3) 0.5657(3) 0.4215(3) 0.0911(12) Uani 1 1 d . U . . .
F9 F 0.1137(4) 0.4796(3) 0.4582(3) 0.0998(14) Uani 1 1 d . . . . .
N7 N 0.6475(4) 0.9968(3) 0.7428(3) 0.0388(8) Uani 1 1 d . . . . .
N8 N 0.7676(3) 0.9614(2) 0.8670(2) 0.0275(6) Uani 1 1 d . . . . .
H8 H 0.822268 0.973661 0.847643 0.033 Uiso 1 1 calc R . . . .
N9 N 0.7699(3) 0.9331(2) 0.9468(2) 0.0276(6) Uani 1 1 d . . . . .
C33 C 0.6711(3) 0.9678(3) 0.8223(3) 0.0280(7) Uani 1 1 d . . . . .
C34 C 0.6059(3) 0.9425(3) 0.8738(3) 0.0276(7) Uani 1 1 d . . . . .
C35 C 0.6718(3) 0.9211(3) 0.9507(3) 0.0262(7) Uani 1 1 d . . . . .
C36 C 0.6484(3) 0.8859(3) 1.0277(3) 0.0263(7) Uani 1 1 d . . . . .
C37 C 0.5400(3) 0.8120(3) 1.0015(3) 0.0346(8) Uani 1 1 d . . . . .
H37 H 0.478666 0.787984 0.935394 0.042 Uiso 1 1 calc R . . . .
C38 C 0.5224(4) 0.7743(3) 1.0716(3) 0.0421(10) Uani 1 1 d . . . . .
H38 H 0.448937 0.723010 1.052866 0.050 Uiso 1 1 calc R . . . .
C39 C 0.6097(4) 0.8097(3) 1.1688(3) 0.0433(10) Uani 1 1 d . . . . .
H39 H 0.596306 0.783346 1.216599 0.052 Uiso 1 1 calc R . . . .
C40 C 0.7164(4) 0.8836(3) 1.1960(3) 0.0420(10) Uani 1 1 d . . . . .
H40 H 0.776486 0.908605 1.263071 0.050 Uiso 1 1 calc R . . . .
C41 C 0.7366(3) 0.9218(3) 1.1261(3) 0.0338(8) Uani 1 1 d . . . . .
H41 H 0.810498 0.972342 1.145209 0.041 Uiso 1 1 calc R . . . .
C42 C 0.3784(3) 0.8367(3) 0.7344(3) 0.0287(7) Uani 1 1 d . . . . .
C43 C 0.3945(3) 0.7484(3) 0.7029(3) 0.0383(9) Uani 1 1 d . . . . .
H43 H 0.462379 0.747833 0.743644 0.046 Uiso 1 1 calc R . . . .
C44 C 0.3124(4) 0.6609(3) 0.6126(3) 0.0460(11) Uani 1 1 d . . . . .
H44 H 0.323200 0.599920 0.591809 0.055 Uiso 1 1 calc R . . . .
C45 C 0.2145(4) 0.6624(3) 0.5527(3) 0.0420(10) Uani 1 1 d . . . . .
C46 C 0.1982(3) 0.7501(4) 0.5831(3) 0.0410(10) Uani 1 1 d . . . . .
H46 H 0.130670 0.750638 0.541488 0.049 Uiso 1 1 calc R . . . .
C47 C 0.2793(3) 0.8376(3) 0.6741(3) 0.0356(9) Uani 1 1 d . . . . .
H47 H 0.267434 0.897871 0.695184 0.043 Uiso 1 1 calc R . . . .
C48 C 0.1289(4) 0.5699(4) 0.4525(4) 0.0589(14) Uani 1 1 d . . . . .
S1 S 1.00526(8) 0.89811(7) 0.56008(7) 0.0296(2) Uani 1 1 d . . . . .
F1 F 0.5173(3) 0.5353(3) 0.1474(3) 0.1016(14) Uani 1 1 d . . . . .
F2 F 0.6347(3) 0.5082(3) 0.0913(2) 0.0863(11) Uani 1 1 d . U . . .
F3 F 0.5889(3) 0.4387(2) 0.1848(2) 0.0712(9) Uani 1 1 d . . . . .
N1 N 1.0279(4) 0.7712(3) 0.7061(3) 0.0422(9) Uani 1 1 d . . . . .
N2 N 0.9706(3) 0.8807(2) 0.8025(2) 0.0284(6) Uani 1 1 d . . . . .
H2 H 0.978594 0.858083 0.851408 0.034 Uiso 1 1 calc R . . . .
N3 N 0.9349(2) 0.9560(2) 0.7992(2) 0.0268(6) Uani 1 1 d . . . . .
C1 C 0.9915(3) 0.8460(3) 0.7218(3) 0.0290(7) Uani 1 1 d . . . . .
C2 C 0.9698(3) 0.9009(3) 0.6622(3) 0.0264(7) Uani 1 1 d . . . . .
C3 C 0.9337(3) 0.9681(3) 0.7137(3) 0.0256(7) Uani 1 1 d . . . . .
C4 C 0.8955(3) 1.0423(3) 0.6876(3) 0.0263(7) Uani 1 1 d . . . . .
C5 C 0.8288(3) 1.0194(3) 0.5847(3) 0.0322(8) Uani 1 1 d . . . . .
H5A H 0.810959 0.956719 0.529753 0.039 Uiso 1 1 calc R . . . .
C6 C 0.7883(3) 1.0891(3) 0.5629(3) 0.0385(9) Uani 1 1 d . . . . .
H6 H 0.741487 1.072749 0.492995 0.046 Uiso 1 1 calc R . . . .
C7 C 0.8156(4) 1.1812(3) 0.6417(4) 0.0422(10) Uani 1 1 d . . . . .
H7 H 0.788802 1.228723 0.625847 0.051 Uiso 1 1 calc R . . . .
C8 C 0.8817(4) 1.2046(3) 0.7436(3) 0.0392(9) Uani 1 1 d . . . . .
H8A H 0.899392 1.267660 0.797920 0.047 Uiso 1 1 calc R . . . .
C9 C 0.9225(3) 1.1363(3) 0.7671(3) 0.0310(8) Uani 1 1 d . . . . .
H9 H 0.968915 1.153311 0.837338 0.037 Uiso 1 1 calc R . . . .
C10 C 0.8867(3) 0.7884(3) 0.4487(3) 0.0278(7) Uani 1 1 d . . . . .
C11 C 0.8972(3) 0.7608(3) 0.3576(3) 0.0404(10) Uani 1 1 d . . . . .
H11 H 0.965489 0.800268 0.356790 0.049 Uiso 1 1 calc R . . . .
C12 C 0.8095(4) 0.6764(3) 0.2678(3) 0.0436(10) Uani 1 1 d . . . . .
H12 H 0.817306 0.658067 0.205400 0.052 Uiso 1 1 calc R . . . .
C13 C 0.7109(3) 0.6189(3) 0.2690(3) 0.0364(9) Uani 1 1 d . . . . .
C14 C 0.6995(4) 0.6462(4) 0.3593(3) 0.0507(12) Uani 1 1 d . . . . .
H14 H 0.630914 0.606515 0.359678 0.061 Uiso 1 1 calc R . . . .
C15 C 0.7872(4) 0.7313(3) 0.4500(3) 0.0437(10) Uani 1 1 d . . . . .
H15 H 0.779018 0.749932 0.512234 0.052 Uiso 1 1 calc R . . . .
C16 C 0.6141(4) 0.5269(4) 0.1733(3) 0.0503(12) Uani 1 1 d . . . . .
H4A H 0.709(4) 0.619(4) 1.005(3) 0.035(11) Uiso 1 1 d . . . . .
H1A H 1.045(4) 0.752(4) 0.756(4) 0.043(13) Uiso 1 1 d . . . . .
H7A H 0.577(4) 0.980(4) 0.707(4) 0.044(13) Uiso 1 1 d . . . . .
H1B H 1.035(4) 0.751(4) 0.659(4) 0.040(14) Uiso 1 1 d . . . . .
H7B H 0.694(5) 1.004(4) 0.717(4) 0.055(16) Uiso 1 1 d . . . . .
H4B H 0.701(5) 0.720(5) 1.025(5) 0.073(18) Uiso 1 1 d . . . . .
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 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'
F F 0.0171 0.0103 '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'
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
Cl1 C49 H49 104.9 . . ?
Cl2 C49 Cl1 113.2(4) . . ?
Cl2 C49 Cl3 115.3(4) . . ?
Cl2 C49 H49 104.9 . . ?
Cl3 C49 Cl1 112.4(4) . . ?
Cl3 C49 H49 104.9 . . ?
Cl1A C49A Cl2A 92.6(18) . . ?
Cl1A C49A Cl3A 105.8(14) . . ?
Cl1A C49A H49A 118.5 . . ?
Cl2A C49A H49A 118.5 . . ?
Cl3A C49A Cl2A 98(2) . . ?
Cl3A C49A H49A 118.5 . . ?
C18 S2 C26 104.27(16) . . ?
C17 N4 H4A 113(3) . . ?
C17 N4 H4B 126(4) . . ?
H4A N4 H4B 119(5) . . ?
N6 N5 H5 124.5 . . ?
C17 N5 H5 124.5 . . ?
C17 N5 N6 111.0(3) . . ?
C19 N6 N5 106.3(3) . . ?
N4 C17 C18 129.0(3) . . ?
N5 C17 N4 123.3(3) . . ?
N5 C17 C18 107.6(3) . . ?
C17 C18 S2 124.4(3) . . ?
C17 C18 C19 105.0(3) . . ?
C19 C18 S2 129.9(3) . . ?
N6 C19 C18 110.0(3) . . ?
N6 C19 C20 118.9(3) . . ?
C18 C19 C20 131.1(3) . . ?
C21 C20 C19 121.4(3) . . ?
C21 C20 C25 118.4(3) . . ?
C25 C20 C19 120.1(3) . . ?
C20 C21 H21 119.8 . . ?
C20 C21 C22 120.4(3) . . ?
C22 C21 H21 119.8 . . ?
C21 C22 H22 119.8 . . ?
C23 C22 C21 120.4(4) . . ?
C23 C22 H22 119.8 . . ?
C22 C23 H23 120.2 . . ?
C22 C23 C24 119.6(4) . . ?
C24 C23 H23 120.2 . . ?
C23 C24 H24 119.7 . . ?
C25 C24 C23 120.5(4) . . ?
C25 C24 H24 119.7 . . ?
C20 C25 H25 119.7 . . ?
C24 C25 C20 120.5(3) . . ?
C24 C25 H25 119.7 . . ?
C27 C26 S2 123.2(3) . . ?
C31 C26 S2 117.4(3) . . ?
C31 C26 C27 119.4(3) . . ?
C26 C27 H27 119.9 . . ?
C26 C27 C28 120.2(3) . . ?
C28 C27 H27 119.9 . . ?
C27 C28 H28 120.0 . . ?
C27 C28 C29 119.9(4) . . ?
C29 C28 H28 120.0 . . ?
C28 C29 C32 118.6(4) . . ?
C30 C29 C28 120.1(4) . . ?
C30 C29 C32 121.3(4) . . ?
C29 C30 H30 120.1 . . ?
C29 C30 C31 119.8(3) . . ?
C31 C30 H30 120.1 . . ?
C26 C31 C30 120.6(3) . . ?
C26 C31 H31 119.7 . . ?
C30 C31 H31 119.7 . . ?
F4 C32 F5 103.0(4) . . ?
F4 C32 C29 112.4(4) . . ?
F5 C32 C29 113.4(4) . . ?
F6 C32 F4 107.0(4) . . ?
F6 C32 F5 106.4(4) . . ?
F6 C32 C29 113.8(4) . . ?
C34 S3 C42 102.98(17) . . ?
C33 N7 H7A 116(3) . . ?
C33 N7 H7B 116(4) . . ?
H7A N7 H7B 122(5) . . ?
N9 N8 H8 124.5 . . ?
C33 N8 H8 124.5 . . ?
C33 N8 N9 110.9(3) . . ?
C35 N9 N8 106.1(3) . . ?
N7 C33 C34 128.7(4) . . ?
N8 C33 N7 123.5(4) . . ?
N8 C33 C34 107.7(3) . . ?
C33 C34 S3 124.4(3) . . ?
C33 C34 C35 104.7(3) . . ?
C35 C34 S3 130.6(3) . . ?
N9 C35 C34 110.5(3) . . ?
N9 C35 C36 118.1(3) . . ?
C34 C35 C36 131.4(3) . . ?
C37 C36 C35 120.9(3) . . ?
C41 C36 C35 120.0(3) . . ?
C41 C36 C37 119.0(4) . . ?
C36 C37 H37 120.1 . . ?
C38 C37 C36 119.8(4) . . ?
C38 C37 H37 120.1 . . ?
C37 C38 H38 119.5 . . ?
C37 C38 C39 121.0(4) . . ?
C39 C38 H38 119.5 . . ?
C38 C39 H39 120.2 . . ?
C40 C39 C38 119.7(4) . . ?
C40 C39 H39 120.2 . . ?
C39 C40 H40 119.8 . . ?
C39 C40 C41 120.4(4) . . ?
C41 C40 H40 119.8 . . ?
C36 C41 H41 120.0 . . ?
C40 C41 C36 120.1(4) . . ?
C40 C41 H41 120.0 . . ?
C43 C42 S3 123.2(3) . . ?
C43 C42 C47 119.6(3) . . ?
C47 C42 S3 117.2(3) . . ?
C42 C43 H43 119.8 . . ?
C44 C43 C42 120.4(4) . . ?
C44 C43 H43 119.8 . . ?
C43 C44 H44 120.2 . . ?
C45 C44 C43 119.7(4) . . ?
C45 C44 H44 120.2 . . ?
C44 C45 C48 119.5(4) . . ?
C46 C45 C44 120.2(4) . . ?
C46 C45 C48 120.2(4) . . ?
C45 C46 H46 119.8 . . ?
C45 C46 C47 120.4(4) . . ?
C47 C46 H46 119.8 . . ?
C42 C47 H47 120.2 . . ?
C46 C47 C42 119.6(4) . . ?
C46 C47 H47 120.2 . . ?
F7 C48 F8 107.8(5) . . ?
F7 C48 F9 105.8(5) . . ?
F7 C48 C45 112.6(4) . . ?
F8 C48 C45 112.7(4) . . ?
F9 C48 F8 104.3(5) . . ?
F9 C48 C45 113.0(5) . . ?
C2 S1 C10 104.58(17) . . ?
C1 N1 H1A 116(3) . . ?
C1 N1 H1B 120(4) . . ?
H1A N1 H1B 124(5) . . ?
N3 N2 H2 124.5 . . ?
C1 N2 H2 124.5 . . ?
C1 N2 N3 111.0(3) . . ?
C3 N3 N2 106.3(3) . . ?
N1 C1 C2 129.2(3) . . ?
N2 C1 N1 123.3(4) . . ?
N2 C1 C2 107.6(3) . . ?
C1 C2 S1 124.7(3) . . ?
C1 C2 C3 105.1(3) . . ?
C3 C2 S1 129.3(3) . . ?
N3 C3 C2 110.0(3) . . ?
N3 C3 C4 118.8(3) . . ?
C2 C3 C4 131.2(3) . . ?
C5 C4 C3 121.0(3) . . ?
C5 C4 C9 119.1(3) . . ?
C9 C4 C3 119.9(3) . . ?
C4 C5 H5A 120.2 . . ?
C6 C5 C4 119.6(4) . . ?
C6 C5 H5A 120.2 . . ?
C5 C6 H6 119.6 . . ?
C7 C6 C5 120.7(4) . . ?
C7 C6 H6 119.6 . . ?
C6 C7 H7 120.0 . . ?
C6 C7 C8 120.0(4) . . ?
C8 C7 H7 120.0 . . ?
C7 C8 H8A 119.9 . . ?
C7 C8 C9 120.3(4) . . ?
C9 C8 H8A 119.9 . . ?
C4 C9 H9 119.8 . . ?
C8 C9 C4 120.3(4) . . ?
C8 C9 H9 119.8 . . ?
C11 C10 S1 116.9(3) . . ?
C11 C10 C15 119.8(3) . . ?
C15 C10 S1 123.3(3) . . ?
C10 C11 H11 119.7 . . ?
C12 C11 C10 120.6(4) . . ?
C12 C11 H11 119.7 . . ?
C11 C12 H12 120.1 . . ?
C13 C12 C11 119.8(4) . . ?
C13 C12 H12 120.1 . . ?
C12 C13 C14 120.0(4) . . ?
C12 C13 C16 121.3(4) . . ?
C14 C13 C16 118.8(4) . . ?
C13 C14 H14 119.7 . . ?
C13 C14 C15 120.6(4) . . ?
C15 C14 H14 119.7 . . ?
C10 C15 C14 119.2(4) . . ?
C10 C15 H15 120.4 . . ?
C14 C15 H15 120.4 . . ?
F1 C16 C13 113.0(4) . . ?
F2 C16 F1 108.2(4) . . ?
F2 C16 F3 104.9(4) . . ?
F2 C16 C13 113.4(4) . . ?
F3 C16 F1 104.1(4) . . ?
F3 C16 C13 112.5(4) . . ?
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 C49 1.740(6) . ?
Cl1A C49A 1.71(2) . ?
Cl2 C49 1.700(7) . ?
Cl2A C49A 1.94(4) . ?
Cl3 C49 1.733(6) . ?
Cl3A C49A 1.720(19) . ?
C49 H49 1.0000 . ?
C49A H49A 1.0000 . ?
S2 C18 1.737(3) . ?
S2 C26 1.773(4) . ?
F4 C32 1.323(6) . ?
F5 C32 1.330(6) . ?
F6 C32 1.311(5) . ?
N4 C17 1.360(5) . ?
N4 H4A 0.86(5) . ?
N4 H4B 0.88(6) . ?
N5 H5 0.8800 . ?
N5 N6 1.372(4) . ?
N5 C17 1.339(4) . ?
N6 C19 1.339(4) . ?
C17 C18 1.397(5) . ?
C18 C19 1.413(5) . ?
C19 C20 1.471(5) . ?
C20 C21 1.389(5) . ?
C20 C25 1.405(5) . ?
C21 H21 0.9500 . ?
C21 C22 1.390(5) . ?
C22 H22 0.9500 . ?
C22 C23 1.378(6) . ?
C23 H23 0.9500 . ?
C23 C24 1.382(6) . ?
C24 H24 0.9500 . ?
C24 C25 1.376(5) . ?
C25 H25 0.9500 . ?
C26 C27 1.382(5) . ?
C26 C31 1.375(5) . ?
C27 H27 0.9500 . ?
C27 C28 1.383(5) . ?
C28 H28 0.9500 . ?
C28 C29 1.388(6) . ?
C29 C30 1.367(6) . ?
C29 C32 1.490(5) . ?
C30 H30 0.9500 . ?
C30 C31 1.390(5) . ?
C31 H31 0.9500 . ?
S3 C34 1.743(4) . ?
S3 C42 1.778(4) . ?
F7 C48 1.313(6) . ?
F8 C48 1.331(6) . ?
F9 C48 1.328(7) . ?
N7 C33 1.360(5) . ?
N7 H7A 0.86(5) . ?
N7 H7B 0.85(6) . ?
N8 H8 0.8800 . ?
N8 N9 1.372(4) . ?
N8 C33 1.342(5) . ?
N9 C35 1.338(5) . ?
C33 C34 1.396(5) . ?
C34 C35 1.410(5) . ?
C35 C36 1.480(5) . ?
C36 C37 1.399(5) . ?
C36 C41 1.396(5) . ?
C37 H37 0.9500 . ?
C37 C38 1.377(6) . ?
C38 H38 0.9500 . ?
C38 C39 1.379(6) . ?
C39 H39 0.9500 . ?
C39 C40 1.377(6) . ?
C40 H40 0.9500 . ?
C40 C41 1.387(6) . ?
C41 H41 0.9500 . ?
C42 C43 1.382(5) . ?
C42 C47 1.391(5) . ?
C43 H43 0.9500 . ?
C43 C44 1.382(6) . ?
C44 H44 0.9500 . ?
C44 C45 1.381(6) . ?
C45 C46 1.374(6) . ?
C45 C48 1.491(6) . ?
C46 H46 0.9500 . ?
C46 C47 1.383(6) . ?
C47 H47 0.9500 . ?
S1 C2 1.745(3) . ?
S1 C10 1.780(4) . ?
F1 C16 1.331(6) . ?
F2 C16 1.323(5) . ?
F3 C16 1.325(6) . ?
N1 C1 1.357(5) . ?
N1 H1A 0.87(5) . ?
N1 H1B 0.73(5) . ?
N2 H2 0.8800 . ?
N2 N3 1.372(4) . ?
N2 C1 1.336(5) . ?
N3 C3 1.341(4) . ?
C1 C2 1.399(5) . ?
C2 C3 1.408(5) . ?
C3 C4 1.463(5) . ?
C4 C5 1.396(5) . ?
C4 C9 1.401(5) . ?
C5 H5A 0.9500 . ?
C5 C6 1.395(6) . ?
C6 H6 0.9500 . ?
C6 C7 1.377(6) . ?
C7 H7 0.9500 . ?
C7 C8 1.379(6) . ?
C8 H8A 0.9500 . ?
C8 C9 1.386(6) . ?
C9 H9 0.9500 . ?
C10 C11 1.380(5) . ?
C10 C15 1.382(5) . ?
C11 H11 0.9500 . ?
C11 C12 1.380(6) . ?
C12 H12 0.9500 . ?
C12 C13 1.374(6) . ?
C13 C14 1.375(6) . ?
C13 C16 1.495(6) . ?
C14 H14 0.9500 . ?
C14 C15 1.390(6) . ?
C15 H15 0.9500 . ?
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
N5 H5 N9 0.88 1.98 2.826(4) 161.5 . yes
N8 H8 N3 0.88 1.98 2.829(4) 162.0 . yes
C43 H43 Cl2 0.95 2.91 3.717(5) 143.9 2_666 yes
N2 H2 N6 0.88 1.96 2.814(4) 164.1 . yes
C15 H15 Cl3 0.95 2.96 3.803(5) 148.0 2_666 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
S2 C18 C19 N6 -170.0(3) . . . . ?
S2 C18 C19 C20 11.6(6) . . . . ?
S2 C26 C27 C28 179.8(3) . . . . ?
S2 C26 C31 C30 179.6(3) . . . . ?
N4 C17 C18 S2 -7.7(6) . . . . ?
N4 C17 C18 C19 -179.2(4) . . . . ?
N5 N6 C19 C18 -0.7(4) . . . . ?
N5 N6 C19 C20 177.9(3) . . . . ?
N5 C17 C18 S2 170.9(2) . . . . ?
N5 C17 C18 C19 -0.6(4) . . . . ?
N6 N5 C17 N4 178.9(3) . . . . ?
N6 N5 C17 C18 0.2(4) . . . . ?
N6 C19 C20 C21 -142.3(3) . . . . ?
N6 C19 C20 C25 34.3(5) . . . . ?
C17 N5 N6 C19 0.3(4) . . . . ?
C17 C18 C19 N6 0.8(4) . . . . ?
C17 C18 C19 C20 -177.6(3) . . . . ?
C18 S2 C26 C27 5.4(4) . . . . ?
C18 S2 C26 C31 -175.2(3) . . . . ?
C18 C19 C20 C21 36.0(5) . . . . ?
C18 C19 C20 C25 -147.4(4) . . . . ?
C19 C20 C21 C22 176.5(3) . . . . ?
C19 C20 C25 C24 -176.2(3) . . . . ?
C20 C21 C22 C23 -0.8(6) . . . . ?
C21 C20 C25 C24 0.6(5) . . . . ?
C21 C22 C23 C24 1.6(6) . . . . ?
C22 C23 C24 C25 -1.4(6) . . . . ?
C23 C24 C25 C20 0.3(6) . . . . ?
C25 C20 C21 C22 -0.3(5) . . . . ?
C26 S2 C18 C17 90.0(3) . . . . ?
C26 S2 C18 C19 -100.8(3) . . . . ?
C26 C27 C28 C29 0.3(7) . . . . ?
C27 C26 C31 C30 -0.9(6) . . . . ?
C27 C28 C29 C30 -0.4(7) . . . . ?
C27 C28 C29 C32 179.2(4) . . . . ?
C28 C29 C30 C31 0.0(6) . . . . ?
C28 C29 C32 F4 -63.3(6) . . . . ?
C28 C29 C32 F5 53.1(6) . . . . ?
C28 C29 C32 F6 174.8(5) . . . . ?
C29 C30 C31 C26 0.7(6) . . . . ?
C30 C29 C32 F4 116.4(5) . . . . ?
C30 C29 C32 F5 -127.2(5) . . . . ?
C30 C29 C32 F6 -5.5(7) . . . . ?
C31 C26 C27 C28 0.4(6) . . . . ?
C32 C29 C30 C31 -179.7(4) . . . . ?
S3 C34 C35 N9 -173.2(3) . . . . ?
S3 C34 C35 C36 9.2(6) . . . . ?
S3 C42 C43 C44 178.9(4) . . . . ?
S3 C42 C47 C46 -179.7(3) . . . . ?
N7 C33 C34 S3 -4.4(6) . . . . ?
N7 C33 C34 C35 -178.5(4) . . . . ?
N8 N9 C35 C34 -0.5(4) . . . . ?
N8 N9 C35 C36 177.4(3) . . . . ?
N8 C33 C34 S3 174.0(3) . . . . ?
N8 C33 C34 C35 -0.1(4) . . . . ?
N9 N8 C33 N7 178.3(3) . . . . ?
N9 N8 C33 C34 -0.3(4) . . . . ?
N9 C35 C36 C37 -138.6(4) . . . . ?
N9 C35 C36 C41 37.6(5) . . . . ?
C33 N8 N9 C35 0.5(4) . . . . ?
C33 C34 C35 N9 0.4(4) . . . . ?
C33 C34 C35 C36 -177.2(3) . . . . ?
C34 S3 C42 C43 23.5(4) . . . . ?
C34 S3 C42 C47 -156.9(3) . . . . ?
C34 C35 C36 C37 38.8(6) . . . . ?
C34 C35 C36 C41 -145.0(4) . . . . ?
C35 C36 C37 C38 174.9(4) . . . . ?
C35 C36 C41 C40 -175.8(4) . . . . ?
C36 C37 C38 C39 1.3(6) . . . . ?
C37 C36 C41 C40 0.5(6) . . . . ?
C37 C38 C39 C40 -0.4(7) . . . . ?
C38 C39 C40 C41 -0.5(7) . . . . ?
C39 C40 C41 C36 0.5(6) . . . . ?
C41 C36 C37 C38 -1.4(6) . . . . ?
C42 S3 C34 C33 78.8(3) . . . . ?
C42 S3 C34 C35 -108.7(4) . . . . ?
C42 C43 C44 C45 1.0(7) . . . . ?
C43 C42 C47 C46 -0.1(6) . . . . ?
C43 C44 C45 C46 -0.7(7) . . . . ?
C43 C44 C45 C48 176.8(5) . . . . ?
C44 C45 C46 C47 -0.1(7) . . . . ?
C44 C45 C48 F7 -79.6(7) . . . . ?
C44 C45 C48 F8 158.2(5) . . . . ?
C44 C45 C48 F9 40.3(7) . . . . ?
C45 C46 C47 C42 0.5(6) . . . . ?
C46 C45 C48 F7 98.0(6) . . . . ?
C46 C45 C48 F8 -24.3(7) . . . . ?
C46 C45 C48 F9 -142.1(5) . . . . ?
C47 C42 C43 C44 -0.6(6) . . . . ?
C48 C45 C46 C47 -177.6(4) . . . . ?
S1 C2 C3 N3 -169.1(3) . . . . ?
S1 C2 C3 C4 12.4(6) . . . . ?
S1 C10 C11 C12 179.6(4) . . . . ?
S1 C10 C15 C14 -179.5(4) . . . . ?
N1 C1 C2 S1 -9.8(6) . . . . ?
N1 C1 C2 C3 179.7(4) . . . . ?
N2 N3 C3 C2 -0.5(4) . . . . ?
N2 N3 C3 C4 178.3(3) . . . . ?
N2 C1 C2 S1 169.7(3) . . . . ?
N2 C1 C2 C3 -0.7(4) . . . . ?
N3 N2 C1 N1 -180.0(4) . . . . ?
N3 N2 C1 C2 0.4(4) . . . . ?
N3 C3 C4 C5 -140.8(3) . . . . ?
N3 C3 C4 C9 36.9(5) . . . . ?
C1 N2 N3 C3 0.1(4) . . . . ?
C1 C2 C3 N3 0.8(4) . . . . ?
C1 C2 C3 C4 -177.8(3) . . . . ?
C2 S1 C10 C11 -173.2(3) . . . . ?
C2 S1 C10 C15 6.7(4) . . . . ?
C2 C3 C4 C5 37.7(6) . . . . ?
C2 C3 C4 C9 -144.6(4) . . . . ?
C3 C4 C5 C6 176.4(3) . . . . ?
C3 C4 C9 C8 -176.6(3) . . . . ?
C4 C5 C6 C7 1.4(6) . . . . ?
C5 C4 C9 C8 1.1(5) . . . . ?
C5 C6 C7 C8 -1.2(6) . . . . ?
C6 C7 C8 C9 1.0(6) . . . . ?
C7 C8 C9 C4 -0.9(6) . . . . ?
C9 C4 C5 C6 -1.3(5) . . . . ?
C10 S1 C2 C1 87.3(3) . . . . ?
C10 S1 C2 C3 -104.6(3) . . . . ?
C10 C11 C12 C13 -0.3(7) . . . . ?
C11 C10 C15 C14 0.4(7) . . . . ?
C11 C12 C13 C14 0.6(7) . . . . ?
C11 C12 C13 C16 -180.0(5) . . . . ?
C12 C13 C14 C15 -0.4(8) . . . . ?
C12 C13 C16 F1 -123.1(5) . . . . ?
C12 C13 C16 F2 0.4(7) . . . . ?
C12 C13 C16 F3 119.3(5) . . . . ?
C13 C14 C15 C10 -0.1(8) . . . . ?
C14 C13 C16 F1 56.3(6) . . . . ?
C14 C13 C16 F2 179.9(5) . . . . ?
C14 C13 C16 F3 -61.2(6) . . . . ?
C15 C10 C11 C12 -0.2(7) . . . . ?
C16 C13 C14 C15 -179.9(5) . . . . ?
