The crystal structure of 3-(1H-benzo[d]imidazol-2-yl)-7-chloro-1-cyclopropyl-6-fluoro-1,4-dihydroquinolin — dimethylsulfoxide (1/1), C21H19ClFN3O2S
Rasras, Anas J.; Sinnokrot, Mutasem; AlDamen, Murad A.; Khanfar, Monther A.; Al-Qawasmeh, Raed A.; Zeitschrift für Kristallographie - New Crystal Structures 234 (2019) 645–647; doi:10.1515/ncrs-2018-0599

data_8105807
_publ_section_title
;
 The crystal structure of
 3-(1H-benzo[d]imidazol-2-yl)-7-chloro-1-cyclopropyl-6-fluoro-1,4-dihydroquinolin
 --- dimethylsulfoxide (1/1), C21H19ClFN3O2S
;
_journal_issue                   4
_journal_name_full
'Zeitschrift f\"ur Kristallographie - New Crystal Structures'
_journal_page_first              645
_journal_page_last               647
_journal_paper_doi               10.1515/ncrs-2018-0599
_journal_volume                  234
_journal_year                    2019
_chemical_formula_moiety         'C19 H13 Cl F N3 O, C2 H6 O S'
_chemical_formula_sum            'C21 H19 Cl F N3 O2 S'
_chemical_formula_weight         431.92
_chemical_name_systematic
;
3-(1H-benzo[d]imidazol-2-yl)-7-chloro-1-cyclopropyl-6-fluoroquinolin-4(1H)-one
 DMSO
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2yn'
_space_group_name_H-M_alt        'P 1 21/n 1'
_atom_sites_solution_primary     dual
_cell_angle_alpha                90
_cell_angle_beta                 99.901(4)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   10.1495(4)
_cell_length_b                   8.9769(5)
_cell_length_c                   22.1431(10)
_cell_measurement_reflns_used    2893
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      28.3470
_cell_measurement_theta_min      3.7280
_cell_volume                     1987.43(16)
_computing_cell_refinement       'CrysAlis^Pro^, Ver. 1.171.38.46 [1]'
_computing_data_collection       'CrysAlis^Pro^, Ver. 1.171.38.46 [1]'
_computing_data_reduction        'CrysAlis^Pro^, Ver. 1.171.38.46 [1]'
_computing_molecular_graphics    'Olex2 [2]'
_computing_publication_material  'Olex2 [2]'
_computing_structure_refinement  'olex2.refine [11]'
_computing_structure_solution    'ShelXT [3]'
_diffrn_ambient_temperature      293
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 16.0534
_diffrn_detector_type            Eos
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_details
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  t~exp~   \w     \q     \k     \f   Frames
--------------------------------------------------------------------------
  1  \w    -34.00  30.00   1.00    3.00    --  -16.36  77.00  60.00   64
  2  \w     35.00  60.00   1.00    3.00    --   16.98 178.00-150.00   25
  3  \w    -88.00 -21.00   1.00    3.00    --  -16.36 -19.00 -60.00   67
  4  \w    -22.00  23.00   1.00    3.00    --  -16.36 -99.00-120.00   45
  5  \w    -17.00  20.00   1.00    3.00    --  -16.36 -99.00  90.00   37
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'Xcalibur, Eos'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0136251000
_diffrn_orient_matrix_UB_12      0.0507383000
_diffrn_orient_matrix_UB_13      -0.0248300000
_diffrn_orient_matrix_UB_21      0.0012077000
_diffrn_orient_matrix_UB_22      0.0599658000
_diffrn_orient_matrix_UB_23      0.0209672000
_diffrn_orient_matrix_UB_31      0.0696108000
_diffrn_orient_matrix_UB_32      0.0088670000
_diffrn_orient_matrix_UB_33      0.0004709000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0198
_diffrn_reflns_av_unetI/netI     0.0338
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       28
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            10584
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_theta_full        29.4284
_diffrn_reflns_theta_max         29.43
_diffrn_reflns_theta_min         2.99
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_source_type              'Enhance (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    0.330
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.85442
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.38.46 [1]
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.4434
_exptl_crystal_description       needle
_exptl_crystal_F_000             897.4850
_exptl_crystal_size_max          0.6
_exptl_crystal_size_mid          0.4
_exptl_crystal_size_min          0.1
_refine_diff_density_max         0.5916
_refine_diff_density_min         -0.4030
_refine_diff_density_rms         0.0730
_refine_ls_extinction_coef       0.004216
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2018/3 (Sheldrick 2018)'
_refine_ls_goodness_of_fit_ref   1.0595
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     276
_refine_ls_number_reflns         4644
_refine_ls_number_restraints     28
_refine_ls_restrained_S_all      1.0595
_refine_ls_R_factor_all          0.0770
_refine_ls_R_factor_gt           0.0473
_refine_ls_shift/su_max          0.0009
_refine_ls_shift/su_mean         0.0002
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0640P)^2^+0.5234P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1198
_refine_ls_wR_factor_ref         0.1418
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3196
_reflns_number_total             4644
_reflns_threshold_expression     I>=2u(I)
_cod_data_source_file            suppl_ncrs-2018-0599_suppl.cif
_cod_data_source_block           exp_2290
_cod_database_code               8105807
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All N(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Ternary CH refined with riding coordinates:
 C9(H9)
2.b Secondary CH2 refined with riding coordinates:
 C10(H10a,H10b), C11(H11a,H11b)
2.c Aromatic/amide H refined with riding coordinates:
 N2'(H2'), C2(H2), C4'(H4'), C8(H8), C7'(H7'), C5(H5), C5'(H5'), C6'(H6')
2.d Idealised Me refined as rotating group:
 C12(H12a,H12b,H12c)
;