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_2021632
_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      orthorhombic
_space_group_IT_number           33
_space_group_name_Hall           'P 2c -2n'
_space_group_name_H-M_alt        'P n a 21'
_symmetry_space_group_name_Hall  'P 2c -2n'
_symmetry_space_group_name_H-M   'P n a 21'
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     difmap
_audit_creation_method           SHELXL-2014
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   8.8623(4)
_cell_length_b                   14.4656(7)
_cell_length_c                   14.2723(7)
_cell_measurement_reflns_used    3084
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      66.991
_cell_measurement_theta_min      4.352
_cell_volume                     1829.69(15)
_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 0.992
_diffrn_measured_fraction_theta_max 0.992
_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  0.0620
_diffrn_reflns_av_unetI/netI     0.0498
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            22910
_diffrn_reflns_theta_full        66.881
_diffrn_reflns_theta_max         66.881
_diffrn_reflns_theta_min         4.352
_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    1.969
_exptl_absorpt_correction_T_max  0.871
_exptl_absorpt_correction_T_min  0.726
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
(SADABS; Bruker, 2015)
;
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.372
_exptl_crystal_description       plate
_exptl_crystal_F_000             792
_exptl_crystal_size_max          0.120
_exptl_crystal_size_mid          0.120
_exptl_crystal_size_min          0.070
_refine_diff_density_max         0.286
_refine_diff_density_min         -0.233
_refine_ls_abs_structure_details
;
Flack <i>x</i> determined using 1075 quotients [(I+)-(I-)]/[(I+)+(I-)]
(Parsons <i>et al.</i>,  2013)
;
_refine_ls_abs_structure_Flack   0.048(9)
_refine_ls_extinction_coef       0.0057(6)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_ref   1.056
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     250
_refine_ls_number_reflns         3083
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.056
_refine_ls_R_factor_all          0.0476
_refine_ls_R_factor_gt           0.0371
_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^)+(0.0509P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0836
_refine_ls_wR_factor_ref         0.0889
_reflns_number_gt                2669
_reflns_number_total             3083
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            ov3128sup1.cif
_cod_data_source_block           II
_cod_database_code               2021632
_cod_database_fobs_code          2021632
_shelx_estimated_absorpt_t_min   0.798
_shelx_estimated_absorpt_t_max   0.874
_shelx_hkl_checksum              11201
_shelx_res_checksum              73413
_shelxl_version_number           2.014