Monoclinic and orthorhombic forms of (<i>RS</i>)-(<i>E</i>)-4-[2-(4-chlorobenzylidene)hydrazinyl]-6,11-dimethyl-6,11-dihydro-5<i>H</i>-benzo[<i>b</i>]pyrimido[5,4-<i>f</i>]azepine: synthesis, concomitant polymorphism and supramolecular assembly mediated by C—H···N, C—H···π(arene) and C—Cl···π(arene) interactions
Acosta Quintero, Lina M.; Palma, Alirio; Choquesillo-Lazarte, Duane; Cobo, Justo; Glidewell, Christopher; Acta Crystallographica Section C 75 (2019) –; doi:10.1107/S205322961900617X

data_2021631
_publ_section_title
;
 Monoclinic and orthorhombic forms of
 (<i>RS</i>)-(<i>E</i>)-4-[2-(4-chlorobenzylidene)hydrazinyl]-6,11-dimethyl-6,11-dihydro-5<i>H</i>-benzo[<i>b</i>]pyrimido[5,4-<i>f</i>]azepine:
 synthesis, concomitant polymorphism and supramolecular assembly mediated
 by C---H&#x00B7;&#x00B7;&#x00B7;N, C---H&#x00B7;&#x00B7;&#x00B7;\p(arene)
 and C---Cl&#x00B7;&#x00B7;&#x00B7;\p(arene) interactions
;
_journal_coeditor_code           OV3128
_journal_issue                   6
_journal_name_full               'Acta Crystallographica Section C'
_journal_page_first
;
;
_journal_paper_doi               10.1107/S205322961900617X
_journal_volume                  75
_journal_year                    2019
_chemical_formula_iupac          'C21 H20 Cl N5'
_chemical_formula_moiety         'C21 H20 Cl N5'
_chemical_formula_sum            'C21 H20 Cl N5'
_chemical_formula_weight         377.87
_chemical_name_systematic
(<i>RS</i>)-(<i>E</i>)-4-[2-(4-Chlorobenzylidene)hydrazinyl]-6,11-dimethyl-6,11-dihydro-5<i>H</i>-benzo[<i>b</i>]pyrimido[5,4-<i>f</i>]azepine
_space_group_crystal_system      monoclinic
_space_group_IT_number           9
_space_group_name_Hall           'C -2yc'
_space_group_name_H-M_alt        'C 1 c 1'
_symmetry_space_group_name_Hall  'C -2yc'
_symmetry_space_group_name_H-M   'C 1 c 1'
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     difmap
_audit_creation_method           SHELXL-2014
_cell_angle_alpha                90
_cell_angle_beta                 123.161(7)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   12.9010(15)
_cell_length_b                   20.055(3)
_cell_length_c                   8.7001(13)
_cell_measurement_reflns_used    3250
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      67.212
_cell_measurement_theta_min      4.409
_cell_volume                     1884.4(5)
_computing_cell_refinement
;
SAINT (Bruker, 2013)
;
_computing_data_collection
;
APEX2 (Bruker, 2014)
;
_computing_data_reduction
;
SAINT (Bruker, 2013)
;
_computing_molecular_graphics
;
PLATON (Spek, 2009)
;
_computing_publication_material
;
SHELXL2014 (Sheldrick, 2015) and PLATON (Spek, 2009)
;
_computing_structure_refinement
;
SHELXL2014 (Sheldrick, 2015)
;
_computing_structure_solution
;
SIR92 (Altomare <i>et al.</i>,  1994)
;
_diffrn_ambient_temperature      100(2)
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measurement_device_type  'Bruker D8 Venture'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_monochromator  'multilayer mirror'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0629
_diffrn_reflns_av_unetI/netI     0.0702
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_k_max       23
_diffrn_reflns_limit_k_min       -23
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_number            11068
_diffrn_reflns_theta_full        67.212
_diffrn_reflns_theta_max         67.212
_diffrn_reflns_theta_min         4.409
_diffrn_source
'INCOATEC high brilliance microfocus sealed tube'
_diffrn_standards_decay_%        0
_diffrn_standards_interval_count 0
_diffrn_standards_interval_time  0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    1.912
_exptl_absorpt_correction_T_max  0.892
_exptl_absorpt_correction_T_min  0.707
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
(SADABS; Bruker, 2015)
;
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.332
_exptl_crystal_description       plate
_exptl_crystal_F_000             792
_exptl_crystal_size_max          0.110
_exptl_crystal_size_mid          0.100
_exptl_crystal_size_min          0.060
_refine_diff_density_max         0.264
_refine_diff_density_min         -0.289
_refine_ls_abs_structure_details
;
Flack <i>x</i> determined using 1264 quotients [(I+)-(I-)]/[(I+)+(I-)]
(Parsons <i>et al.</i>,  2013)
;
_refine_ls_abs_structure_Flack   0.011(11)
_refine_ls_extinction_coef       0.0033(5)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_extinction_method
;
SHELXL2014 (Sheldrick, 2015)
;
_refine_ls_goodness_of_fit_ref   1.045
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     250
_refine_ls_number_reflns         3280
_refine_ls_number_restraints     2
_refine_ls_restrained_S_all      1.045
_refine_ls_R_factor_all          0.0504
_refine_ls_R_factor_gt           0.0415
_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^)+(0.0435P)^2^+0.6400P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0973
_refine_ls_wR_factor_ref         0.1047
_reflns_number_gt                2886
_reflns_number_total             3280
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            ov3128sup1.cif
_cod_data_source_block           I
_cod_database_code               2021631
_cod_database_fobs_code          2021631
_shelx_estimated_absorpt_t_min   0.817
_shelx_estimated_absorpt_t_max   0.894
_shelx_hkl_checksum              8830
_shelx_res_checksum              24183
_shelxl_version_number           2.014