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#$Date: 2023-05-09 10:32:38 +0300 (Tue, 09 May 2023) $
#$Revision: 283608 $
#$URL: file:///home/coder/svn-repositories/cod/cif/8/10/71/8107135.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_8107135
loop_
_publ_author_name
'El-Hiti, Gamal A.'
'Abdel-Wahab, Bakr F.'
'Hegazy, Amany S.'
'Ajarim, Mansour D.'
'Kariuki, Benson M.'
_publ_section_title
;
 Crystal structure of
 4-(benzofuran-2-yl)-2-(3-(4-fluorophenyl)-3,3a,4,5-tetrahydro-2H-benzo[g]indazol-2-yl)thiazole,
 C28H20FN3OS
;
_journal_issue                   4
_journal_name_full
'Zeitschrift für Kristallographie - New Crystal Structures'
_journal_page_first              1171
_journal_page_last               1173
_journal_paper_doi               10.1515/ncrs-2016-0113
_journal_volume                  231
_journal_year                    2016
_chemical_formula_moiety         'C28 H20 F N3 O S'
_chemical_formula_sum            'C28 H20 F N3 O S'
_chemical_formula_weight         465.53
_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
_cell_angle_alpha                95.470(4)
_cell_angle_beta                 102.133(4)
_cell_angle_gamma                97.962(4)
_cell_formula_units_Z            2
_cell_length_a                   9.5719(5)
_cell_length_b                   10.7499(6)
_cell_length_c                   10.9238(5)
_cell_measurement_reflns_used    3645
_cell_measurement_temperature    150(2)
_cell_measurement_theta_max      28.3590
_cell_measurement_theta_min      3.8360
_cell_volume                     1079.30(10)
_computing_cell_refinement       'CrysAlis PRO [12]'
_computing_data_collection       'CrysAlis PRO [12]'
_computing_data_reduction        'CrysAlis PRO [12]'
_computing_molecular_graphics    'ORTEP-3 for Windows'
_computing_publication_material  'WinGX [13] and CHEMDRAW Ultra [14]'
_computing_structure_refinement  'SHELXS2013 [11]'
_computing_structure_solution    'SHELXS2013 [11]'
_diffrn_ambient_temperature      150(2)
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.825
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, Atlas'
_diffrn_measurement_method       'ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0248
_diffrn_reflns_av_unetI/netI     0.0491
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.825
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_number            9220
_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.825
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         29.731
_diffrn_reflns_theta_min         3.446
_diffrn_source                   'SuperNova (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    0.187
_exptl_absorpt_correction_T_max  0.996
_exptl_absorpt_correction_T_min  0.991
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35g (release 09-12-2014 CrysAlis171 .NET)
(compiled Dec  9 2014,15:38:47)
Numerical absorption correction based on gaussian integration over
			a multifaceted crystal model
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.432
_exptl_crystal_description       plate
_exptl_crystal_F_000             484
_exptl_crystal_size_max          0.198
_exptl_crystal_size_mid          0.141
_exptl_crystal_size_min          0.097
_refine_diff_density_max         0.299
_refine_diff_density_min         -0.289
_refine_diff_density_rms         0.052
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.043
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     307
_refine_ls_number_reflns         5066
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.043
_refine_ls_R_factor_all          0.0683
_refine_ls_R_factor_gt           0.0482
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0405P)²+0.4069P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1006
_refine_ls_wR_factor_ref         0.1143
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                3916
_reflns_number_total             5066
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            suppl_ncrs-2016-0113_suppl.cif
_cod_data_source_block           bmk1558b
_cod_database_code               8107135
_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   0.964
_shelx_estimated_absorpt_t_max   0.982
_shelxl_version_number           2013-4
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
C1 C -0.14281(18) 0.11637(17) 0.67571(17) 0.0246(4) Uani 1 1 d . . . . .
H1 H -0.1328 0.1399 0.5912 0.030 Uiso 1 1 calc R U . . .
C2 C -0.08131(17) -0.00434(17) 0.69912(16) 0.0227(4) Uani 1 1 d . . . . .
C3 C -0.07582(19) -0.09076(18) 0.59862(17) 0.0278(4) Uani 1 1 d . . . . .
H3 H -0.1074 -0.0721 0.5150 0.033 Uiso 1 1 calc R U . . .
C4 C -0.0253(2) -0.20383(18) 0.61704(17) 0.0285(4) Uani 1 1 d . . . . .
H4 H -0.0213 -0.2624 0.5476 0.034 Uiso 1 1 calc R U . . .
C5 C 0.01878(18) -0.22837(17) 0.73945(18) 0.0264(4) Uani 1 1 d . . . . .
C6 C 0.01447(19) -0.14668(18) 0.84189(17) 0.0282(4) Uani 1 1 d . . . . .
H6 H 0.0450 -0.1668 0.9251 0.034 Uiso 1 1 calc R U . . .
C7 C -0.03553(19) -0.03385(18) 0.82147(17) 0.0275(4) Uani 1 1 d . . . . .
H7 H -0.0387 0.0243 0.8916 0.033 Uiso 1 1 calc R U . . .
C8 C -0.30185(18) 0.11105(17) 0.68765(17) 0.0249(4) Uani 1 1 d . . . . .
H8 H -0.3495 0.1645 0.6267 0.030 Uiso 1 1 calc R U . . .
C9 C -0.28178(18) 0.17815(16) 0.81924(17) 0.0232(4) Uani 1 1 d . . . . .
C10 C -0.39902(18) 0.16903(17) 0.88609(17) 0.0245(4) Uani 1 1 d . . . . .
C11 C -0.52773(19) 0.08579(18) 0.82889(18) 0.0277(4) Uani 1 1 d . . . . .
C12 C -0.54500(19) 0.00729(19) 0.70234(19) 0.0323(4) Uani 1 1 d . . . . .
H12A H -0.5969 0.0509 0.6353 0.039 Uiso 1 1 calc R U . . .
H12B H -0.6055 -0.0754 0.7015 0.039 Uiso 1 1 calc R U . . .
C13 C -0.40109(19) -0.01597(18) 0.67175(18) 0.0280(4) Uani 1 1 d . . . . .
H13A H -0.3554 -0.0720 0.7293 0.034 Uiso 1 1 calc R U . . .
H13B H -0.4181 -0.0578 0.5840 0.034 Uiso 1 1 calc R U . . .
C14 C -0.3859(2) 0.24056(18) 1.00242(18) 0.0296(4) Uani 1 1 d . . . . .
H14 H -0.2976 0.2950 1.0414 0.036 Uiso 1 1 calc R U . . .
C15 C -0.5004(2) 0.2326(2) 1.06119(19) 0.0350(5) Uani 1 1 d . . . . .
H15 H -0.4920 0.2828 1.1396 0.042 Uiso 1 1 calc R U . . .
C16 C -0.6285(2) 0.1507(2) 1.0049(2) 0.0382(5) Uani 1 1 d . . . . .
H16 H -0.7076 0.1447 1.0451 0.046 Uiso 1 1 calc R U . . .
C17 C -0.6407(2) 0.0783(2) 0.8910(2) 0.0343(5) Uani 1 1 d . . . . .
H17 H -0.7283 0.0220 0.8540 0.041 Uiso 1 1 calc R U . . .
C18 C 0.06315(18) 0.28820(17) 0.79507(17) 0.0243(4) Uani 1 1 d . . . . .
C19 C 0.27786(18) 0.35947(17) 0.76643(17) 0.0254(4) Uani 1 1 d . . . . .
C20 C 0.2901(2) 0.42708(18) 0.88014(18) 0.0297(4) Uani 1 1 d . . . . .
H20 H 0.3735 0.4849 0.9247 0.036 Uiso 1 1 calc R U . . .
C21 C 0.38786(19) 0.36524(17) 0.69299(18) 0.0273(4) Uani 1 1 d . . . . .
C22 C 0.38299(19) 0.32063(17) 0.57326(17) 0.0266(4) Uani 1 1 d . . . . .
H22 H 0.3011 0.2734 0.5142 0.032 Uiso 1 1 calc R U . . .
C23 C 0.52349(19) 0.35703(17) 0.55059(18) 0.0260(4) Uani 1 1 d . . . . .
C24 C 0.60774(19) 0.42322(17) 0.66407(17) 0.0248(4) Uani 1 1 d . . . . .
C25 C 0.5896(2) 0.33990(19) 0.44821(19) 0.0346(5) Uani 1 1 d . . . . .
H25 H 0.5358 0.2972 0.3686 0.042 Uiso 1 1 calc R U . . .
C26 C 0.7360(2) 0.3875(2) 0.4673(2) 0.0379(5) Uani 1 1 d . . . . .
H26 H 0.7826 0.3767 0.3993 0.045 Uiso 1 1 calc R U . . .
C27 C 0.8156(2) 0.4498(2) 0.5820(2) 0.0388(5) Uani 1 1 d . . . . .
H27 H 0.9160 0.4792 0.5917 0.047 Uiso 1 1 calc R U . . .
C28 C 0.7527(2) 0.47028(19) 0.6832(2) 0.0336(5) Uani 1 1 d . . . . .
H28 H 0.8068 0.5147 0.7620 0.040 Uiso 1 1 calc R U . . .
N1 N -0.15439(15) 0.24229(14) 0.86502(14) 0.0241(3) Uani 1 1 d . . . . .
N2 N -0.07305(16) 0.22275(14) 0.77533(14) 0.0266(3) Uani 1 1 d . . . . .
N3 N 0.14703(15) 0.27865(14) 0.71629(14) 0.0253(3) Uani 1 1 d . . . . .
O1 O 0.52411(13) 0.43076(12) 0.75277(12) 0.0288(3) Uani 1 1 d . . . . .
S1 S 0.13323(5) 0.39370(5) 0.93305(5) 0.03009(14) Uani 1 1 d . . . . .
F1 F 0.06926(12) -0.33894(11) 0.75986(10) 0.0352(3) Uani 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'
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'
F F 0.0171 0.0103 '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
N2 C1 C2 112.24(14) . .
N2 C1 C8 99.35(13) . .
C2 C1 C8 114.47(15) . .
N2 C1 H1 110.1 . .
C2 C1 H1 110.1 . .
C8 C1 H1 110.1 . .
C3 C2 C7 118.39(17) . .
C3 C2 C1 120.31(15) . .
C7 C2 C1 121.23(16) . .
C2 C3 C4 121.60(17) . .
C2 C3 H3 119.2 . .
C4 C3 H3 119.2 . .
C5 C4 C3 117.76(17) . .
C5 C4 H4 121.1 . .
C3 C4 H4 121.1 . .
F1 C5 C6 118.30(16) . .
F1 C5 C4 118.78(16) . .
C6 C5 C4 122.93(17) . .
C5 C6 C7 118.41(17) . .
C5 C6 H6 120.8 . .
C7 C6 H6 120.8 . .
C6 C7 C2 120.90(17) . .
C6 C7 H7 119.5 . .
C2 C7 H7 119.5 . .
C9 C8 C13 110.19(15) . .
C9 C8 C1 101.39(14) . .
C13 C8 C1 120.35(15) . .
C9 C8 H8 108.1 . .
C13 C8 H8 108.1 . .
C1 C8 H8 108.1 . .
N1 C9 C10 124.33(16) . .
N1 C9 C8 114.12(16) . .
C10 C9 C8 121.55(15) . .
C14 C10 C11 120.41(17) . .
C14 C10 C9 121.79(16) . .
C11 C10 C9 117.80(17) . .
C17 C11 C10 118.11(18) . .
C17 C11 C12 120.43(17) . .
C10 C11 C12 121.46(17) . .
C11 C12 C13 113.63(15) . .
C11 C12 H12A 108.8 . .
C13 C12 H12A 108.8 . .
C11 C12 H12B 108.8 . .
C13 C12 H12B 108.8 . .
H12A C12 H12B 107.7 . .
C8 C13 C12 108.63(15) . .
C8 C13 H13A 110.0 . .
C12 C13 H13A 110.0 . .
C8 C13 H13B 110.0 . .
C12 C13 H13B 110.0 . .
H13A C13 H13B 108.3 . .
C15 C14 C10 120.29(19) . .
C15 C14 H14 119.9 . .
C10 C14 H14 119.9 . .
C14 C15 C16 119.6(2) . .
C14 C15 H15 120.2 . .
C16 C15 H15 120.2 . .
C17 C16 C15 120.13(19) . .
C17 C16 H16 119.9 . .
C15 C16 H16 119.9 . .
C16 C17 C11 121.42(19) . .
C16 C17 H17 119.3 . .
C11 C17 H17 119.3 . .
N3 C18 N2 124.07(17) . .
N3 C18 S1 116.61(13) . .
N2 C18 S1 119.32(14) . .
C20 C19 N3 116.36(16) . .
C20 C19 C21 125.64(17) . .
N3 C19 C21 118.00(16) . .
C19 C20 S1 110.58(14) . .
C19 C20 H20 124.7 . .
S1 C20 H20 124.7 . .
C22 C21 O1 111.46(16) . .
C22 C21 C19 131.79(17) . .
O1 C21 C19 116.73(16) . .
C21 C22 C23 107.36(16) . .
C21 C22 H22 126.3 . .
C23 C22 H22 126.3 . .
C24 C23 C25 118.21(17) . .
C24 C23 C22 105.80(16) . .
C25 C23 C22 135.97(18) . .
C28 C24 O1 126.19(17) . .
C28 C24 C23 124.05(18) . .
O1 C24 C23 109.74(15) . .
C26 C25 C23 117.78(19) . .
C26 C25 H25 121.1 . .
C23 C25 H25 121.1 . .
C27 C26 C25 121.93(19) . .
C27 C26 H26 119.0 . .
C25 C26 H26 119.0 . .
C26 C27 C28 121.5(2) . .
C26 C27 H27 119.3 . .
C28 C27 H27 119.3 . .
C24 C28 C27 116.5(2) . .
C24 C28 H28 121.7 . .
C27 C28 H28 121.7 . .
C9 N1 N2 106.85(14) . .
C18 N2 N1 119.21(15) . .
C18 N2 C1 127.25(15) . .
N1 N2 C1 112.97(14) . .
C18 N3 C19 108.55(15) . .
C24 O1 C21 105.61(14) . .
C20 S1 C18 87.91(9) . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
C1 N2 1.478(2) .
C1 C2 1.519(2) .
C1 C8 1.549(2) .
C1 H1 1.0000 .
C2 C3 1.384(3) .
C2 C7 1.397(2) .
C3 C4 1.386(3) .
C3 H3 0.9500 .
C4 C5 1.377(3) .
C4 H4 0.9500 .
C5 F1 1.364(2) .
C5 C6 1.366(3) .
C6 C7 1.385(3) .
C6 H6 0.9500 .
C7 H7 0.9500 .
C8 C9 1.507(3) .
C8 C13 1.524(2) .
C8 H8 1.0000 .
C9 N1 1.287(2) .
C9 C10 1.459(2) .
C10 C14 1.393(3) .
C10 C11 1.405(3) .
C11 C17 1.390(3) .
C11 C12 1.514(3) .
C12 C13 1.531(3) .
C12 H12A 0.9900 .
C12 H12B 0.9900 .
C13 H13A 0.9900 .
C13 H13B 0.9900 .
C14 C15 1.380(3) .
C14 H14 0.9500 .
C15 C16 1.392(3) .
C15 H15 0.9500 .
C16 C17 1.378(3) .
C16 H16 0.9500 .
C17 H17 0.9500 .
C18 N3 1.301(2) .
C18 N2 1.356(2) .
C18 S1 1.7454(18) .
C19 C20 1.352(3) .
C19 N3 1.394(2) .
C19 C21 1.450(3) .
C20 S1 1.7238(19) .
C20 H20 0.9500 .
C21 C22 1.338(3) .
C21 O1 1.387(2) .
C22 C23 1.427(3) .
C22 H22 0.9500 .
C23 C24 1.395(3) .
C23 C25 1.405(3) .
C24 C28 1.374(3) .
C24 O1 1.384(2) .
C25 C26 1.388(3) .
C25 H25 0.9500 .
C26 C27 1.377(3) .
C26 H26 0.9500 .
C27 C28 1.379(3) .
C27 H27 0.9500 .
C28 H28 0.9500 .
N1 N2 1.392(2) .
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
C6 H6 N1 0.95 2.57 3.508(2) 170.8 2_557
