Crystal structures of two 4<i>H</i>-chromene derivatives: 2-amino-3-cyano-4-(3,4-dichlorophenyl)-7-hydroxy-4<i>H</i>-benzo[1,2-<i>b</i>]pyran 1,4-dioxane monosolvate and 2-amino-3-cyano-4-(2,6-dichlorophenyl)-7-hydroxy-4<i>H</i>-benzo[1,2-<i>b</i>]pyran
Silambarasan, S.; Nasser, A. Jamal Abdul; Mohandas, T.; Acta Crystallographica Section E 75 (2019) 1568–1572; doi:10.1107/S2056989019013197

data_2243110
_publ_section_title
;
 Crystal structures of two 4<i>H</i>-chromene derivatives:
 2-amino-3-cyano-4-(3,4-dichlorophenyl)-7-hydroxy-4<i>H</i>-benzo[1,2-<i>b</i>]pyran
 1,4-dioxane monosolvate and
 2-amino-3-cyano-4-(2,6-dichlorophenyl)-7-hydroxy-4<i>H</i>-benzo[1,2-<i>b</i>]pyran
;
_journal_coeditor_code           YK2126
_journal_issue                   10
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              1568
_journal_page_last               1572
_journal_paper_doi               10.1107/S2056989019013197
_journal_volume                  75
_journal_year                    2019
_chemical_formula_iupac          'C16 H9 Cl2 N2 O2, C4 H8 O2'
_chemical_formula_moiety         'C16 H9 Cl2 N2 O2, C4 H8 O2'
_chemical_formula_sum            'C20 H17 Cl2 N2 O4'
_chemical_formula_weight         420.25
_chemical_melting_point          520
_chemical_name_systematic
'2-Amino-3-cyano-4-(3,4-dichlorophenyl)-7-hydroxy-4<i>H</i>-benzo[1,2-<i>b</i>]pyran 1,4-dioxane monosolvate'
_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   difmap
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-2014/6
_cell_angle_alpha                90
_cell_angle_beta                 102.95(3)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   12.753(9)
_cell_length_b                   6.665(4)
_cell_length_c                   24.050(14)
_cell_measurement_reflns_used    9965
_cell_measurement_temperature    294(2)
_cell_measurement_theta_max      26.66
_cell_measurement_theta_min      3.17
_cell_volume                     1992(2)
_computing_cell_refinement
;
APEX3 and SAINT (Bruker, 2018)
;
_computing_data_collection
;
APEX3 (Bruker, 2018)
;
_computing_data_reduction
;
SAINT and XPREP (Bruker, 2018)
;
_computing_molecular_graphics
;
DIAMOND (Brandenburg, 2007) and Mercury (Macrae <i>et al.</i>,
2008)
;
_computing_publication_material
;
PLATON (Spek, 2009)
;
_computing_structure_refinement
;
<i>SHELXL2014/6</i> (Sheldrick, 2015b)
;
_computing_structure_solution
;
<i>SHELXT2014/5</i> (Sheldrick, 2015a)
;
_diffrn_ambient_temperature      294(2)
_diffrn_measured_fraction_theta_full 0.973
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_device_type  'Bruker Kappa APEX3 CMOS'
_diffrn_measurement_method       '\w and \f scan'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0334
_diffrn_reflns_av_unetI/netI     0.0180
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_l_max       26
_diffrn_reflns_limit_l_min       -28
_diffrn_reflns_number            34682
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         24.998
_diffrn_reflns_theta_min         3.178
_exptl_absorpt_coefficient_mu    0.355
_exptl_absorpt_correction_T_max  0.7454
_exptl_absorpt_correction_T_min  0.7035
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
(SADABS; Bruker, 2018)
;
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.401
_exptl_crystal_density_method    none
_exptl_crystal_description       block
_exptl_crystal_F_000             868
_exptl_crystal_size_max          0.150
_exptl_crystal_size_mid          0.150
_exptl_crystal_size_min          0.100
_refine_diff_density_max         0.260
_refine_diff_density_min         -0.240
_refine_ls_extinction_coef       0.0174(18)
_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   1.107
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     256
_refine_ls_number_reflns         3492
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.107
_refine_ls_R_factor_all          0.0554
_refine_ls_R_factor_gt           0.0435
_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^)+(0.0541P)^2^+1.1852P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1124
_refine_ls_wR_factor_ref         0.1213
_reflns_number_gt                2885
_reflns_number_total             3492
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            yk2126sup1.cif
_cod_data_source_block           I
_cod_database_code               2243110
_shelx_estimated_absorpt_t_min   0.949
_shelx_estimated_absorpt_t_max   0.965
_shelx_hkl_checksum              87033
_shelx_res_checksum              17686
_shelxl_version_number           2014/6
_cod_database_fobs_code 2243110