#------------------------------------------------------------------------------
#$Date: 2021-03-06 08:20:24 +0200 (Sat, 06 Mar 2021) $
#$Revision: 262792 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/24/37/2243771.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/. The original data for this entry
# were provided by IUCr Journals, http://journals.iucr.org/.
#
# The file may be used within the scientific community so long as
# proper attribution is given to the journal article from which the
# data were obtained.
#
data_2243771
loop_
_publ_author_name
'Harish Chinthal, Chayanna'
'Yathirajan, Hemmige S.'
'Manju, Nagaraja'
'Kalluraya, Balakrishna'
'Foro, Sabine'
'Glidewell, Christopher'
_publ_section_title
;
 Reduced 3,4'-bipyrazoles carrying thiophene and thiazole substituents:
 structures of two intermediates and two products
;
_journal_coeditor_code           DX2035
_journal_issue                   4
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              335
_journal_page_last               340
_journal_paper_doi               10.1107/S2056989021002310
_journal_volume                  77
_journal_year                    2021
_chemical_formula_iupac          'C32 H22 Br Cl2 N5 O S2'
_chemical_formula_moiety         'C32 H22 Br Cl2 N5 O S2'
_chemical_formula_sum            'C32 H22 Br Cl2 N5 O S2'
_chemical_formula_weight         707.47
_chemical_name_systematic
4-(4-Bromophenyl)-2-[5'-(2,4-dichlorophenoxy)-3'-methyl-1'-phenyl-5-(thiophen-2-yl)-3,4-dihydro-1'H,2H-3,4'-bipyrazole-2-yl]-4-thiazole
_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     difmap
_audit_creation_method           SHELXL-2014
_cell_angle_alpha                117.202(8)
_cell_angle_beta                 102.879(7)
_cell_angle_gamma                105.727(7)
_cell_formula_units_Z            2
_cell_length_a                   12.3200(9)
_cell_length_b                   12.5700(9)
_cell_length_c                   12.7742(9)
_cell_measurement_reflns_used    6664
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      27.781
_cell_measurement_theta_min      2.609
_cell_volume                     1548.4(3)
_computing_cell_refinement
;
CrysAlis RED (Oxford Diffraction, 2009)
;
_computing_data_collection
;
CrysAlis CCD (Oxford Diffraction, 2009)
;
_computing_data_reduction
;
CrysAlis RED (Oxford Diffraction, 2009)
;
_computing_molecular_graphics
;
PLATON (Spek, 2020)
;
_computing_publication_material
;
SHELXL-2014 (Sheldrick, 2015b) and PLATON (Spek, 2020)
;
_computing_structure_refinement
;
SHELXL-2014 (Sheldrick, 2015b)
;
_computing_structure_solution
;
SHELXT (Sheldrick, 2015a)
;
_diffrn_ambient_temperature      296(2)
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type
;
Oxford Diffraction Xcalibur
with Sapphire CCD detector
;
_diffrn_measurement_method       'ω scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0221
_diffrn_reflns_av_unetI/netI     0.0486
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_number            10549
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         25.547
_diffrn_reflns_theta_min         2.609
_diffrn_source                   'Enhance (Mo) X-ray Source'
_diffrn_standards_decay_%        0
_diffrn_standards_interval_count 0
_diffrn_standards_interval_time  0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    1.670
_exptl_absorpt_correction_T_max  0.875
_exptl_absorpt_correction_T_min  0.779
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
(CrysAlis RED; Oxford Diffraction, 2009)
;
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.517
_exptl_crystal_description       plate
_exptl_crystal_F_000             716
_exptl_crystal_size_max          0.400
_exptl_crystal_size_mid          0.400
_exptl_crystal_size_min          0.080
_refine_diff_density_max         0.470
_refine_diff_density_min         -0.341
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.929
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     402
_refine_ls_number_reflns         5773
_refine_ls_number_restraints     10
_refine_ls_restrained_S_all      0.928
_refine_ls_R_factor_all          0.0886
_refine_ls_R_factor_gt           0.0388
_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)+(0.0475P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0835
_refine_ls_wR_factor_ref         0.0946
_reflns_number_gt                3158
_reflns_number_total             5773
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            dx2035sup1.cif
_cod_data_source_block           III
_cod_original_cell_volume        1548.4(2)
_cod_database_code               2243771
_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   0.555
_shelx_estimated_absorpt_t_max   0.878
_shelxl_version_number           2.014
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'
loop_
_atom_site_type_symbol
_atom_site_label
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_calc_flag
_atom_site_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
N N1 0.5457(2) 0.3735(2) 0.86216(19) 0.0478(5) Uani d 1 . .
N N2 0.4327(2) 0.3754(2) 0.8277(2) 0.0514(6) Uani d 1 . .
C C3 0.4368(3) 0.4319(2) 0.7616(2) 0.0495(7) Uani d 1 . .
C C4 0.5508(3) 0.4674(2) 0.7522(2) 0.0477(7) Uani d 1 . .
C C5 0.6162(2) 0.4278(2) 0.8157(2) 0.0446(6) Uani d 1 . .
C C11 0.5693(3) 0.3119(2) 0.9294(2) 0.0449(6) Uani d 1 . .
C C12 0.6877(3) 0.3383(3) 0.9963(3) 0.0552(7) Uani d 1 . .
H H12 0.7546 0.3982 0.9997 0.066 Uiso calc 1 . .
C C13 0.7064(3) 0.2750(3) 1.0586(3) 0.0591(8) Uani d 1 . .
H H13 0.7863 0.2915 1.1029 0.071 Uiso calc 1 . .
C C14 0.6089(3) 0.1887(3) 1.0558(3) 0.0630(8) Uani d 1 . .
H H14 0.6221 0.1465 1.0978 0.076 Uiso calc 1 . .
C C15 0.4917(3) 0.1647(3) 0.9907(3) 0.0719(9) Uani d 1 . .
H H15 0.4252 0.1064 0.9893 0.086 Uiso calc 1 . .
C C16 0.4707(3) 0.2257(3) 0.9271(3) 0.0617(8) Uani d 1 . .
H H16 0.3906 0.2088 0.8830 0.074 Uiso calc 1 . .
C C31 0.3270(3) 0.4476(3) 0.7047(3) 0.0686(8) Uani d 1 . .
H H31A 0.3053 0.4075 0.6140 0.103 Uiso calc 1 . .
H H31B 0.3464 0.5402 0.7453 0.103 Uiso calc 1 . .
H H31C 0.2589 0.4054 0.7181 0.103 Uiso calc 1 . .
N N41 0.7375(3) 0.5162(3) 0.5905(3) 0.0661(7) Uani d 1 . .
N N42 0.6211(2) 0.4547(3) 0.5794(2) 0.0670(7) Uani d 1 . .
C C43 0.5928(3) 0.5358(3) 0.6881(3) 0.0576(7) Uani d 1 . .
H H43 0.5288 0.5591 0.6567 0.069 Uiso calc 1 . .
C C44 0.7168(3) 0.6608(3) 0.7729(3) 0.0672(8) Uani d 1 . .
H H44A 0.7058 0.7390 0.7866 0.081 Uiso calc 1 . .
H H44B 0.7546 0.6741 0.8558 0.081 Uiso calc 1 . .
C C45 0.7931(3) 0.6315(3) 0.6965(3) 0.0622(8) Uani d 1 . .
S S421 0.59658(8) 0.25102(9) 0.35914(8) 0.0776(3) Uani d 1 . .
C C422 0.5442(3) 0.3311(3) 0.4739(3) 0.0576(8) Uani d 1 . .
N N423 0.4313(2) 0.2671(2) 0.4522(2) 0.0554(6) Uani d 1 . .
C C424 0.3781(3) 0.1417(3) 0.3379(3) 0.0568(7) Uani d 1 . .
C C425 0.4545(3) 0.1182(3) 0.2773(3) 0.0724(9) Uani d 1 . .
H H425 0.4325 0.0394 0.2004 0.087 Uiso calc 1 . .
C C441 0.2509(3) 0.0523(3) 0.2964(3) 0.0557(7) Uani d 1 . .
C C442 0.1828(3) 0.0877(3) 0.3669(3) 0.0663(8) Uani d 1 . .
H H442 0.2188 0.1712 0.4429 0.080 Uiso calc 1 . .
C C443 0.0635(3) 0.0037(3) 0.3287(3) 0.0738(9) Uani d 1 . .
H H443 0.0196 0.0310 0.3783 0.089 Uiso calc 1 . .
C C444 0.0085(3) -0.1208(3) 0.2172(3) 0.0667(8) Uani d 1 . .
Br Br44 -0.15403(3) -0.23859(4) 0.16704(4) 0.09399(17) Uani d 1 . .
C C445 0.0740(4) -0.1594(3) 0.1453(3) 0.0803(10) Uani d 1 . .
H H445 0.0378 -0.2435 0.0700 0.096 Uiso calc 1 . .
C C446 0.1919(4) -0.0751(3) 0.1836(3) 0.0778(9) Uani d 1 . .
H H446 0.2349 -0.1030 0.1331 0.093 Uiso calc 1 . .
S S451 0.99714(13) 0.68706(13) 0.64070(13) 0.1055(6) Uani d 0.947(4) A 1
C C452 0.9177(3) 0.7199(4) 0.7353(4) 0.0739(9) Uani d 0.947(4) A 1
C C453 0.9844(6) 0.8384(6) 0.8487(6) 0.0934(17) Uani d 0.947(4) A 1
H H453 0.9561 0.8733 0.9127 0.112 Uiso calc 0.947(4) A 1
C C454 1.1069(5) 0.9043(5) 0.8577(6) 0.1124(18) Uani d 0.947(4) A 1
H H454 1.1665 0.9865 0.9289 0.135 Uiso calc 0.947(4) A 1
C C455 1.1232(5) 0.8339(6) 0.7532(7) 0.1145(18) Uani d 0.947(4) A 1
H H455 1.1955 0.8612 0.7421 0.137 Uiso calc 0.947(4) A 1
S S551 1.025(3) 0.871(2) 0.863(3) 0.0934(17) Uani d 0.053(4) A 2
C C552 0.9177(3) 0.7199(4) 0.7353(4) 0.0739(9) Uani d 0.053(4) A 2
C C553 0.966(5) 0.658(5) 0.654(6) 0.1055(6) Uani d 0.053(4) A 2
H H553 0.9264 0.5696 0.5857 0.127 Uiso calc 0.053(4) A 2
C C554 1.090(5) 0.750(6) 0.687(7) 0.1145(18) Uani d 0.053(4) A 2
H H554 1.1374 0.7270 0.6403 0.137 Uiso calc 0.053(4) A 2
C C555 1.126(7) 0.868(8) 0.790(10) 0.1124(18) Uani d 0.053(4) A 2
H H555 1.1972 0.9419 0.8192 0.135 Uiso calc 0.053(4) A 2
O O51 0.73172(16) 0.43438(16) 0.83109(15) 0.0493(4) Uani d 1 . .
C C51 0.7387(2) 0.3304(2) 0.7303(2) 0.0440(6) Uani d 1 . .
C C52 0.8521(2) 0.3502(3) 0.7240(3) 0.0488(7) Uani d 1 . .
Cl Cl52 0.97805(7) 0.50033(8) 0.83960(9) 0.0895(3) Uani d 1 . .
C C53 0.8662(3) 0.2526(3) 0.6269(3) 0.0586(8) Uani d 1 . .
H H53 0.9429 0.2664 0.6230 0.070 Uiso calc 1 . .
C C54 0.7648(3) 0.1344(3) 0.5356(3) 0.0563(7) Uani d 1 . .
Cl Cl54 0.77954(9) 0.01019(9) 0.41070(8) 0.0873(3) Uani d 1 . .
C C55 0.6533(3) 0.1136(3) 0.5414(3) 0.0634(8) Uani d 1 . .
H H55 0.5856 0.0330 0.4793 0.076 Uiso calc 1 . .
C C56 0.6397(3) 0.2115(3) 0.6391(3) 0.0576(7) Uani d 1 . .
H H56 0.5628 0.1966 0.6428 0.069 Uiso calc 1 . .
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'
Br Br -0.2901 2.4595 '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'
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_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle
_geom_angle_publ_flag
C5 N1 N2 . . 109.84(19) ?
C5 N1 C11 . . 130.5(2) ?
N2 N1 C11 . . 119.5(2) ?
C3 N2 N1 . . 105.3(2) ?
N2 C3 C4 . . 111.7(2) ?
N2 C3 C31 . . 120.5(2) ?
C4 C3 C31 . . 127.7(2) ?
C5 C4 C3 . . 104.5(2) ?
C5 C4 C43 . . 127.4(3) ?
C3 C4 C43 . . 128.1(2) ?
C4 C5 N1 . . 108.7(2) ?
C4 C5 O51 . . 128.6(2) ?
N1 C5 O51 . . 122.7(2) ?
C12 C11 C16 . . 120.1(2) ?
C12 C11 N1 . . 121.3(2) ?
C16 C11 N1 . . 118.6(2) ?
C11 C12 C13 . . 119.4(3) ?
C11 C12 H12 . . 120.3 ?
C13 C12 H12 . . 120.3 ?
C14 C13 C12 . . 120.7(3) ?
C14 C13 H13 . . 119.7 ?
C12 C13 H13 . . 119.7 ?
C13 C14 C15 . . 119.5(3) ?
C13 C14 H14 . . 120.2 ?
C15 C14 H14 . . 120.2 ?
C14 C15 C16 . . 120.9(3) ?
C14 C15 H15 . . 119.6 ?
C16 C15 H15 . . 119.6 ?
C11 C16 C15 . . 119.4(3) ?
C11 C16 H16 . . 120.3 ?
C15 C16 H16 . . 120.3 ?
C3 C31 H31A . . 109.5 ?
C3 C31 H31B . . 109.5 ?
H31A C31 H31B . . 109.5 ?
C3 C31 H31C . . 109.5 ?
H31A C31 H31C . . 109.5 ?
H31B C31 H31C . . 109.5 ?
C45 N41 N42 . . 108.5(3) ?
C422 N42 N41 . . 119.3(3) ?
C422 N42 C43 . . 126.7(3) ?
N41 N42 C43 . . 114.0(2) ?
N42 C43 C4 . . 113.5(2) ?
N42 C43 C44 . . 100.3(2) ?
C4 C43 C44 . . 115.3(2) ?
N42 C43 H43 . . 109.1 ?
C4 C43 H43 . . 109.1 ?
C44 C43 H43 . . 109.1 ?
C45 C44 C43 . . 103.5(2) ?
C45 C44 H44A . . 111.1 ?
C43 C44 H44A . . 111.1 ?
C45 C44 H44B . . 111.1 ?
C43 C44 H44B . . 111.1 ?
H44A C44 H44B . . 109.0 ?
N41 C45 C452 . . 121.5(3) ?
N41 C45 C44 . . 113.6(3) ?
C452 C45 C44 . . 124.8(3) ?
C425 S421 C422 . . 87.62(16) ?
N423 C422 N42 . . 123.9(3) ?
N423 C422 S421 . . 116.5(2) ?
N42 C422 S421 . . 119.6(3) ?
C422 N423 C424 . . 109.9(3) ?
C425 C424 N423 . . 113.9(3) ?
C425 C424 C441 . . 127.3(3) ?
N423 C424 C441 . . 118.8(3) ?
C424 C425 S421 . . 112.0(2) ?
C424 C425 H425 . . 124.0 ?
S421 C425 H425 . . 124.0 ?
C442 C441 C446 . . 116.2(3) ?
C442 C441 C424 . . 121.8(3) ?
C446 C441 C424 . . 122.0(3) ?
C443 C442 C441 . . 122.0(3) ?
C443 C442 H442 . . 119.0 ?
C441 C442 H442 . . 119.0 ?
C442 C443 C444 . . 120.1(3) ?
C442 C443 H443 . . 119.9 ?
C444 C443 H443 . . 119.9 ?
C445 C444 C443 . . 119.3(3) ?
C445 C444 Br44 . . 120.4(3) ?
C443 C444 Br44 . . 120.3(3) ?
C446 C445 C444 . . 120.1(3) ?
C446 C445 H445 . . 120.0 ?
C444 C445 H445 . . 120.0 ?
C445 C446 C441 . . 122.3(3) ?
C445 C446 H446 . . 118.9 ?
C441 C446 H446 . . 118.9 ?
C452 S451 C455 . . 92.0(3) ?
C453 C452 C45 . . 124.7(4) ?
C453 C452 S451 . . 112.1(3) ?
C45 C452 S451 . . 123.2(3) ?
C452 C453 C454 . . 111.1(6) ?
C452 C453 H453 . . 124.4 ?
C454 C453 H453 . . 124.4 ?
C455 C454 C453 . . 112.2(5) ?
C455 C454 H454 . . 123.9 ?
C453 C454 H454 . . 123.9 ?
C454 C455 S451 . . 112.5(4) ?
C454 C455 H455 . . 123.8 ?
S451 C455 H455 . . 123.8 ?
C554 C553 H553 . . 124.5 ?
C555 C554 C553 . . 111.9(12) ?
C555 C554 H554 . . 124.0 ?
C553 C554 H554 . . 124.0 ?
C554 C555 S551 . . 112.0(15) ?
C554 C555 H555 . . 124.0 ?
S551 C555 H555 . . 124.0 ?
C5 O51 C51 . . 115.95(19) ?
C56 C51 C52 . . 119.1(2) ?
C56 C51 O51 . . 123.4(2) ?
C52 C51 O51 . . 117.5(2) ?
C53 C52 C51 . . 120.9(3) ?
C53 C52 Cl52 . . 119.7(2) ?
C51 C52 Cl52 . . 119.4(2) ?
C54 C53 C52 . . 118.8(3) ?
C54 C53 H53 . . 120.6 ?
C52 C53 H53 . . 120.6 ?
C55 C54 C53 . . 120.7(3) ?
C55 C54 Cl54 . . 119.5(2) ?
C53 C54 Cl54 . . 119.8(2) ?
C54 C55 C56 . . 120.3(3) ?
C54 C55 H55 . . 119.8 ?
C56 C55 H55 . . 119.8 ?
C51 C56 C55 . . 120.1(3) ?
C51 C56 H56 . . 119.9 ?
C55 C56 H56 . . 119.9 ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_site_symmetry_2
_geom_bond_distance
_geom_bond_publ_flag
N1 C5 . 1.361(3) ?
N1 N2 . 1.374(3) ?
N1 C11 . 1.428(3) ?
N2 C3 . 1.330(3) ?
C3 C4 . 1.404(3) ?
C3 C31 . 1.495(3) ?
C4 C5 . 1.361(3) ?
C4 C43 . 1.506(3) ?
C5 O51 . 1.367(3) ?
C11 C12 . 1.375(3) ?
C11 C16 . 1.375(3) ?
C12 C13 . 1.385(3) ?
C12 H12 . 0.9300 ?
C13 C14 . 1.364(4) ?
C13 H13 . 0.9300 ?
C14 C15 . 1.366(4) ?
C14 H14 . 0.9300 ?
C15 C16 . 1.379(4) ?
C15 H15 . 0.9300 ?
C16 H16 . 0.9300 ?
C31 H31A . 0.9600 ?
C31 H31B . 0.9600 ?
C31 H31C . 0.9600 ?
N41 C45 . 1.287(4) ?
N41 N42 . 1.372(3) ?
N42 C422 . 1.359(4) ?
N42 C43 . 1.484(3) ?
C43 C44 . 1.543(4) ?
C43 H43 . 0.9800 ?
C44 C45 . 1.496(4) ?
C44 H44A . 0.9700 ?
C44 H44B . 0.9700 ?
C45 C452 . 1.439(4) ?
S421 C425 . 1.717(3) ?
S421 C422 . 1.734(3) ?
C422 N423 . 1.295(3) ?
N423 C424 . 1.399(3) ?
C424 C425 . 1.356(4) ?
C424 C441 . 1.460(4) ?
C425 H425 . 0.9300 ?
C441 C442 . 1.373(4) ?
C441 C446 . 1.400(4) ?
C442 C443 . 1.372(4) ?
C442 H442 . 0.9300 ?
C443 C444 . 1.377(4) ?
C443 H443 . 0.9300 ?
C444 C445 . 1.366(4) ?
C444 Br44 . 1.888(3) ?
C445 C446 . 1.359(4) ?
C445 H445 . 0.9300 ?
C446 H446 . 0.9300 ?
S451 C452 . 1.696(4) ?
S451 C455 . 1.706(6) ?
C452 C453 . 1.351(7) ?
C453 C454 . 1.461(10) ?
C453 H453 . 0.9300 ?
C454 C455 . 1.321(7) ?
C454 H454 . 0.9300 ?
C455 H455 . 0.9300 ?
S551 C555 . 1.707(12) ?
C553 C554 . 1.461(14) ?
C553 H553 . 0.9300 ?
C554 C555 . 1.322(12) ?
C554 H554 . 0.9300 ?
C555 H555 . 0.9300 ?
O51 C51 . 1.395(3) ?
C51 C56 . 1.366(3) ?
C51 C52 . 1.379(3) ?
C52 C53 . 1.377(4) ?
C52 Cl52 . 1.730(3) ?
C53 C54 . 1.374(4) ?
C53 H53 . 0.9300 ?
C54 C55 . 1.353(4) ?
C54 Cl54 . 1.737(3) ?
C55 C56 . 1.379(4) ?
C55 H55 . 0.9300 ?
C56 H56 . 0.9300 ?
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_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion
_geom_torsion_publ_flag
C5 N1 N2 C3 . . . . -0.4(3) ?
C11 N1 N2 C3 . . . . -176.7(2) ?
N1 N2 C3 C4 . . . . -0.1(3) ?
N1 N2 C3 C31 . . . . 178.2(2) ?
N2 C3 C4 C5 . . . . 0.6(3) ?
C31 C3 C4 C5 . . . . -177.6(2) ?
N2 C3 C4 C43 . . . . -178.6(2) ?
C31 C3 C4 C43 . . . . 3.2(4) ?
C3 C4 C5 N1 . . . . -0.8(3) ?
C43 C4 C5 N1 . . . . 178.3(2) ?
C3 C4 C5 O51 . . . . 177.3(2) ?
C43 C4 C5 O51 . . . . -3.5(4) ?
N2 N1 C5 C4 . . . . 0.8(3) ?
C11 N1 C5 C4 . . . . 176.5(2) ?
N2 N1 C5 O51 . . . . -177.4(2) ?
C11 N1 C5 O51 . . . . -1.7(4) ?
C5 N1 C11 C12 . . . . 22.9(4) ?
N2 N1 C11 C12 . . . . -161.7(2) ?
C5 N1 C11 C16 . . . . -157.7(3) ?
N2 N1 C11 C16 . . . . 17.7(3) ?
C16 C11 C12 C13 . . . . 1.5(4) ?
N1 C11 C12 C13 . . . . -179.1(2) ?
C11 C12 C13 C14 . . . . -1.0(4) ?
C12 C13 C14 C15 . . . . 0.0(4) ?
C13 C14 C15 C16 . . . . 0.5(5) ?
C12 C11 C16 C15 . . . . -1.0(4) ?
N1 C11 C16 C15 . . . . 179.6(2) ?
C14 C15 C16 C11 . . . . 0.0(4) ?
C45 N41 N42 C422 . . . . 179.6(2) ?
C45 N41 N42 C43 . . . . 0.5(3) ?
C422 N42 C43 C4 . . . . 55.9(4) ?
N41 N42 C43 C4 . . . . -125.0(3) ?
C422 N42 C43 C44 . . . . 179.5(2) ?
N41 N42 C43 C44 . . . . -1.4(3) ?
C5 C4 C43 N42 . . . . 63.0(4) ?
C3 C4 C43 N42 . . . . -118.0(3) ?
C5 C4 C43 C44 . . . . -51.9(4) ?
C3 C4 C43 C44 . . . . 127.1(3) ?
N42 C43 C44 C45 . . . . 1.7(2) ?
C4 C43 C44 C45 . . . . 124.0(2) ?
N42 N41 C45 C452 . . . . 179.8(2) ?
N42 N41 C45 C44 . . . . 0.8(3) ?
C43 C44 C45 N41 . . . . -1.7(3) ?
C43 C44 C45 C452 . . . . 179.3(2) ?
N41 N42 C422 N423 . . . . -177.2(2) ?
C43 N42 C422 N423 . . . . 1.9(4) ?
N41 N42 C422 S421 . . . . 2.6(3) ?
C43 N42 C422 S421 . . . . -178.31(19) ?
C425 S421 C422 N423 . . . . -1.6(2) ?
C425 S421 C422 N42 . . . . 178.6(2) ?
N42 C422 N423 C424 . . . . -178.4(2) ?
S421 C422 N423 C424 . . . . 1.8(3) ?
C422 N423 C424 C425 . . . . -1.0(3) ?
C422 N423 C424 C441 . . . . 179.2(2) ?
N423 C424 C425 S421 . . . . -0.1(3) ?
C441 C424 C425 S421 . . . . 179.6(2) ?
C422 S421 C425 C424 . . . . 0.9(2) ?
C425 C424 C441 C442 . . . . 179.8(3) ?
N423 C424 C441 C442 . . . . -0.5(4) ?
C425 C424 C441 C446 . . . . 0.8(4) ?
N423 C424 C441 C446 . . . . -179.5(2) ?
C446 C441 C442 C443 . . . . -0.5(4) ?
C424 C441 C442 C443 . . . . -179.6(3) ?
C441 C442 C443 C444 . . . . 0.5(5) ?
C442 C443 C444 C445 . . . . -0.1(5) ?
C442 C443 C444 Br44 . . . . 178.1(2) ?
C443 C444 C445 C446 . . . . -0.3(5) ?
Br44 C444 C445 C446 . . . . -178.5(2) ?
C444 C445 C446 C441 . . . . 0.3(5) ?
C442 C441 C446 C445 . . . . 0.1(4) ?
C424 C441 C446 C445 . . . . 179.2(3) ?
N41 C45 C452 C453 . . . . -175.4(5) ?
C44 C45 C452 C453 . . . . 3.4(6) ?
N41 C45 C452 S451 . . . . 5.6(4) ?
C44 C45 C452 S451 . . . . -175.5(2) ?
C455 S451 C452 C453 . . . . -0.1(4) ?
C455 S451 C452 C45 . . . . 179.0(3) ?
C45 C452 C453 C454 . . . . -179.4(4) ?
S451 C452 C453 C454 . . . . -0.3(6) ?
C452 C453 C454 C455 . . . . 0.6(7) ?
C453 C454 C455 S451 . . . . -0.6(7) ?
C452 S451 C455 C454 . . . . 0.4(5) ?
C553 C554 C555 S551 . . . . 8(16) ?
C4 C5 O51 C51 . . . . -84.1(3) ?
N1 C5 O51 C51 . . . . 93.9(3) ?
C5 O51 C51 C56 . . . . -17.9(3) ?
C5 O51 C51 C52 . . . . 162.1(2) ?
C56 C51 C52 C53 . . . . 0.5(4) ?
O51 C51 C52 C53 . . . . -179.5(2) ?
C56 C51 C52 Cl52 . . . . -179.80(19) ?
O51 C51 C52 Cl52 . . . . 0.2(3) ?
C51 C52 C53 C54 . . . . 0.1(4) ?
Cl52 C52 C53 C54 . . . . -179.63(19) ?
C52 C53 C54 C55 . . . . -0.5(4) ?
C52 C53 C54 Cl54 . . . . 179.2(2) ?
C53 C54 C55 C56 . . . . 0.3(4) ?
Cl54 C54 C55 C56 . . . . -179.3(2) ?
C52 C51 C56 C55 . . . . -0.7(4) ?
O51 C51 C56 C55 . . . . 179.4(2) ?
C54 C55 C56 C51 . . . . 0.3(4) ?

_cod_database_fobs_code 2243771
