Crystal structure, Hirshfeld surface analysis and interaction energy and DFT studies of (S)-10-propargylpyrrolo[2,1-c][1,4]benzodiazepine-5,11-dione
Jeroundi, Dounia; Mazzah, Ahmed; Hökelek, Tuncer; El Hadrami, El Mestafa; Renard, Catherine; Haoudi, Amal; Essassi, El Mokhtar; Acta Crystallographica Section E Crystallographic Communications 76 (2020) 467–; doi:10.1107/S2056989020002698

data_2021993
_publ_section_title
;
 Crystal structure, Hirshfeld surface analysis and interaction energy and
 DFT studies of
 (S)-10-propargylpyrrolo[2,1-c][1,4]benzodiazepine-5,11-dione
;
_journal_coeditor_code           LH5947
_journal_issue                   4
_journal_name_full
'Acta Crystallographica Section E Crystallographic Communications'
_journal_page_first              467
_journal_paper_doi               10.1107/S2056989020002698
_journal_volume                  76
_journal_year                    2020
_chemical_absolute_configuration syn
_chemical_formula_iupac          'C15 H14 N2 O2'
_chemical_formula_moiety         'C15 H14 N2 O2'
_chemical_formula_sum            'C15 H14 N2 O2'
_chemical_formula_weight         254.28
_chemical_name_common            NA8
_chemical_name_systematic
(<i>S</i>)-10-(Prop-2-yn-1-yl)pyrrolo[2,1-<i>c</i>][1,4]benzodiazepine-5,11-dione
_space_group_crystal_system      monoclinic
_space_group_IT_number           4
_space_group_name_Hall           'P 2yb'
_space_group_name_H-M_alt        'P 1 21 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_creation_method
;
Olex2 1.2
(compiled 2018.04.03 svn.r3497 for OlexSys, GUI svn.r5486)
;
_cell_angle_alpha                90
_cell_angle_beta                 116.9210(10)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   8.4959(2)
_cell_length_b                   9.6479(2)
_cell_length_c                   8.7619(2)
_cell_measurement_reflns_used    6478
_cell_measurement_temperature    299.16
_cell_measurement_theta_max      28.50
_cell_measurement_theta_min      2.61
_cell_volume                     640.36(3)
_computing_cell_refinement
;
SAINT (Bruker, 2013)
;
_computing_data_collection
;
APEX3 (Bruker, 2013)
;
_computing_data_reduction
;
SAINT (Bruker, 2013)
;
_computing_molecular_graphics
;
<i>OLEX2</i> (Dolomanov <i>et al.</i>,  2009)
;
_computing_publication_material
;
<i>OLEX2</i> (Dolomanov <i>et al.</i>,  2009)
;
_computing_structure_refinement
;
SHELXL (Sheldrick, 2015b)
;
_computing_structure_solution
;
SHELXT (Sheldrick, 2015a)
;
_diffrn_ambient_temperature      299.16
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type  'Bruker APEXII CCD'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0241
_diffrn_reflns_av_unetI/netI     0.0232
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            12206
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         30.483
_diffrn_reflns_theta_min         2.607
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.089
_exptl_absorpt_correction_T_max  0.7461
_exptl_absorpt_correction_T_min  0.6839
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
(SADABS; Bruker, 2013)
;
_exptl_crystal_colour            'clear light colourless'
_exptl_crystal_density_diffrn    1.319
_exptl_crystal_description       plate
_exptl_crystal_F_000             268
_exptl_crystal_size_max          0.39
_exptl_crystal_size_mid          0.369
_exptl_crystal_size_min          0.155
_refine_diff_density_max         0.199
_refine_diff_density_min         -0.151
_refine_ls_abs_structure_details
;
Flack <i>x</i> determined using 1347 quotients
[(<i>I</i>^+^)-(<i>I</i>^-^)]/[(<i>I</i>^+^)+(<i>I</i>^-^)]
(Parsons <i>et al.</i>,  2013)
;
_refine_ls_abs_structure_Flack   -0.4(3)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.061
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     172
_refine_ls_number_reflns         3821
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.061
_refine_ls_R_factor_all          0.0463
_refine_ls_R_factor_gt           0.0389
_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/[\s^2^(Fo^2^)+(0.0554P)^2^+0.0351P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0983
_refine_ls_wR_factor_ref         0.1032
_reflns_number_gt                3349
_reflns_number_total             3821
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            lh5947sup1.cif
_cod_data_source_block           I
_cod_original_sg_symbol_H-M      'P 21'
_cod_database_code               2021993
_cod_database_fobs_code          2021993
_shelx_estimated_absorpt_t_min   0.966
_shelx_estimated_absorpt_t_max   0.986
_shelx_hkl_checksum              73947
_shelx_res_checksum              66545