Crystal structure, DFT and Hirshfeld surface analysis of 2-amino-4-(2-chlorophenyl)-7-hydroxy-4<i>H</i>-benzo[1,2-<i>b</i>]pyran-3-carbonitrile
Beemarao, M.; Silambarasan, S.; Nasser, A. Jamal Abdul; Purushothaman, M.; Ravichandran, K.; Acta Crystallographica Section E 75 (2019) 1638–1642; doi:10.1107/S2056989019013537

data_2243153
_publ_section_title
;
 Crystal structure, DFT and Hirshfeld surface analysis of
 2-amino-4-(2-chlorophenyl)-7-hydroxy-4<i>H</i>-benzo[1,2-<i>b</i>]pyran-3-carbonitrile
;
_journal_coeditor_code           SJ5577
_journal_issue                   11
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              1638
_journal_page_last               1642
_journal_paper_doi               10.1107/S2056989019013537
_journal_volume                  75
_journal_year                    2019
_chemical_formula_iupac          'C16 H11 Cl N2 O2'
_chemical_formula_moiety         'C16 H11 Cl N2 O2'
_chemical_formula_sum            'C16 H11 Cl N2 O2'
_chemical_formula_weight         298.72
_chemical_name_systematic
2-Amino-4-(2-chlorophenyl)-7-hydroxy-4<i>H</i>-benzo[1,2-<i>b</i>]pyran-3-carbonitrile
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2ybc'
_space_group_name_H-M_alt        'P 1 21/c 1'
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 1 21/c 1'
_atom_sites_solution_hydrogens   geom
_audit_creation_method           SHELXL-2018/3
_cell_angle_alpha                90
_cell_angle_beta                 106.088(2)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   6.6658(3)
_cell_length_b                   30.1600(16)
_cell_length_c                   7.2193(4)
_cell_measurement_reflns_used    2115
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      26.705
_cell_measurement_theta_min      2.701
_cell_volume                     1394.53(12)
_computing_cell_refinement
;
<i>SAINT</i> (Bruker, 2008)
;
_computing_data_collection
;
<i>APEX2</i> (Bruker, 2008)
;
_computing_data_reduction
;
<i>SAINT</i> (Bruker, 2008)
;
_computing_molecular_graphics
;
<i>ORTEP-3</i> (Farrugia, 2012)
;
_computing_publication_material
;
<i>SHELXL97</i> (Sheldrick, 2008) and <i>PLATON</i> (Spek, 2009)
;
_computing_structure_refinement
;
SHELXL2018 (Sheldrick, 2015)
;
_computing_structure_solution
;
<i>SHELXS97</i> (Sheldrick, 2008)
;
_diffrn_ambient_temperature      296(2)
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measurement_device_type  'Bruker SMART APEXII CCD'
_diffrn_measurement_method       '\w and \f scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0335
_diffrn_reflns_av_unetI/netI     0.0230
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_k_max       38
_diffrn_reflns_limit_k_min       -38
_diffrn_reflns_limit_l_max       8
_diffrn_reflns_limit_l_min       -9
_diffrn_reflns_number            21888
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.705
_diffrn_reflns_theta_min         2.701
_diffrn_source                   'fine-focus sealed tube'
_exptl_absorpt_coefficient_mu    0.279
_exptl_absorpt_correction_T_max  0.973
_exptl_absorpt_correction_T_min  0.959
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
(<i>SADABS</i>; Bruker, 2008)
;
_exptl_crystal_colour            'White Crystalline'
_exptl_crystal_density_diffrn    1.423
_exptl_crystal_description       Block
_exptl_crystal_F_000             616
_exptl_crystal_size_max          0.150
_exptl_crystal_size_mid          0.100
_exptl_crystal_size_min          0.100
_refine_diff_density_max         0.193
_refine_diff_density_min         -0.285
_refine_ls_extinction_coef       0.0061(13)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_extinction_method
;
SHELXL2018 (Sheldrick, 2015)
;
_refine_ls_goodness_of_fit_ref   1.054
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     191
_refine_ls_number_reflns         2941
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.054
_refine_ls_R_factor_all          0.0638
_refine_ls_R_factor_gt           0.0374
_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^+0.5426P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0863
_refine_ls_wR_factor_ref         0.1026
_reflns_number_gt                2115
_reflns_number_total             2941
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            sj5577sup1.cif
_cod_data_source_block           I
_cod_database_code               2243153
_cod_database_fobs_code          2243153
_shelx_estimated_absorpt_t_min   0.959
_shelx_estimated_absorpt_t_max   0.973
_shelx_hkl_checksum              65609
_shelx_res_checksum              23172