Crystal structure and Hirshfeld surface analysis of a new benzodiazepine derivative: 4-dichloromethyl-2,3-dihydro-1<i>H</i>-1,5-benzodiazepin-2-one
Chkirate, Karim; Kansiz, Sevgi; Karrouchi, Khalid; Mague, Joel T.; Dege, Necmi; Essassi, El Mokhtar; Acta Crystallographica Section E 75 (2019) 33–37; doi:10.1107/S205698901801681X

data_2242780
_publ_section_title
;
 Crystal structure and Hirshfeld surface analysis of a new benzodiazepine
 derivative:
 4-dichloromethyl-2,3-dihydro-1<i>H</i>-1,5-benzodiazepin-2-one
;
_journal_coeditor_code           XU5953
_journal_issue                   1
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              33
_journal_page_last               37
_journal_paper_doi               10.1107/S205698901801681X
_journal_volume                  75
_journal_year                    2019
_chemical_formula_iupac          'C10 H8 Cl2 N2 O'
_chemical_formula_moiety         'C10 H8 Cl2 N2 O'
_chemical_formula_sum            'C10 H8 Cl2 N2 O'
_chemical_formula_weight         243.08
_chemical_name_systematic
;
4-Dichloromethyl-2,3-dihydro-1<i>H</i>-1,5-benzodiazepin-2-one
;
_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'
_symmetry_space_group_name_Hall  '-P 2yn'
_symmetry_space_group_name_H-M   'P 1 21/n 1'
_atom_sites_solution_hydrogens   difmap
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-2018/1
_cell_angle_alpha                90
_cell_angle_beta                 95.7400(10)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   12.1783(6)
_cell_length_b                   5.7217(3)
_cell_length_c                   14.8258(7)
_cell_measurement_reflns_used    7262
_cell_measurement_temperature    150(2)
_cell_measurement_theta_max      74.5618
_cell_measurement_theta_min      2.9957
_cell_volume                     1027.89(9)
_computing_cell_refinement
;
<i>SAINT</i> (Bruker, 2016)
;
_computing_data_collection
;
<i>APEX3</i> (Bruker, 2016)
;
_computing_data_reduction
;
<i>SAINT</i> (Bruker, 2016)
;
_computing_molecular_graphics
;
<i>DIAMOND</i> (Brandenburg & Putz, 2012) and Mercury (Macrae <i>et
al.</i>,  2008)
;
_computing_publication_material
;
<i>SHELXTL</i> (Sheldrick, 2008)
;
_computing_structure_refinement
;
<i>SHELXL2018</i> (Sheldrick, 2015<i>b</i>)
;
_computing_structure_solution
;
<i>SHELXT</i> (Sheldrick, 2015<i>a</i>)
;
_diffrn_ambient_temperature      150(2)
_diffrn_detector_area_resol_mean 10.4167
_diffrn_measured_fraction_theta_full 0.991
_diffrn_measured_fraction_theta_max 0.976
_diffrn_measurement_device_type  'Bruker D8 VENTURE PHOTON 100 CMOS'
_diffrn_measurement_method       '\w scans'
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0275
_diffrn_reflns_av_unetI/netI     0.0246
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_k_min       -6
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            7403
_diffrn_reflns_theta_full        69.000
_diffrn_reflns_theta_max         74.554
_diffrn_reflns_theta_min         4.484
_diffrn_source                   'INCOATEC I\mS micro-focus source'
_exptl_absorpt_coefficient_mu    5.461
_exptl_absorpt_correction_T_max  0.51
_exptl_absorpt_correction_T_min  0.36
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
(<i>SADABS</i>; Krause <i>et al.</i>, 2015)
;
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.571
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             496
_exptl_crystal_size_max          0.328
_exptl_crystal_size_mid          0.241
_exptl_crystal_size_min          0.142
_refine_diff_density_max         0.323
_refine_diff_density_min         -0.307
_refine_ls_extinction_coef       0.0137(7)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_extinction_method
;
<i>SHELXL2018</i> (Sheldrick, 2015<i>b</i>)
;
_refine_ls_goodness_of_fit_ref   1.045
_refine_ls_hydrogen_treatment    refall
_refine_ls_matrix_type           full
_refine_ls_number_parameters     169
_refine_ls_number_reflns         2051
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.045
_refine_ls_R_factor_all          0.0285
_refine_ls_R_factor_gt           0.0282
_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/[\s^2^(Fo^2^)+(0.0392P)^2^+0.5990P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0735
_refine_ls_wR_factor_ref         0.0737
_reflns_number_gt                2020
_reflns_number_total             2051
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            xu5953sup1.cif
_cod_data_source_block           I
_cod_database_code               2242780
_cod_database_fobs_code          2242780
_shelx_estimated_absorpt_t_min   0.267
_shelx_estimated_absorpt_t_max   0.511
_shelx_hkl_checksum              27864
_shelx_res_checksum              29378