Concomitant polymorphs of 2-imino-2H-chromene-3-carboxylic acid amide: experimental and quantum chemical study.
Shishkina, Svitlana V.; Shaposhnyk, Anna M.; Konovalova, Irina S.; Dyakonenko, Victoriya V.; Vaksler, Yevhenii O.; Acta crystallographica Section B, Structural science, crystal engineering and materials 80 (2024) –; doi:10.1107/S2052520623010193

data_2312377
_publ_section_title
;
 Concomitant polymorphs of 2-imino-2H-chromene-3-carboxylic acid amide:
 experimental and quantum chemical study.
;
_journal_issue                   1
_journal_name_full
'Acta crystallographica Section B, Structural science, crystal engineering and materials'
_journal_paper_doi               10.1107/S2052520623010193
_journal_volume                  80
_journal_year                    2024
_chemical_formula_moiety         'C10 H8 N2 O2'
_chemical_formula_sum            'C10 H8 N2 O2'
_chemical_formula_weight         188.18
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_atom_sites_solution_hydrogens   mixed
_audit_creation_date             2023-08-20
_audit_creation_method
;
Olex2 1.5
(compiled 2023.03.06 svn.rbb2c1857 for OlexSys, GUI svn.r6748)
;
_cell_angle_alpha                91.482(12)
_cell_angle_beta                 98.773(14)
_cell_angle_gamma                109.115(16)
_cell_formula_units_Z            2
_cell_length_a                   7.0199(12)
_cell_length_b                   7.0720(13)
_cell_length_c                   9.6216(12)
_cell_measurement_reflns_used    444
_cell_measurement_temperature    296.15
_cell_measurement_theta_max      24.3210
_cell_measurement_theta_min      3.5550
_cell_volume                     444.57(13)
_computing_cell_refinement       'CrysAlisPro 1.171.39.46 (Rigaku OD, 2018)'
_computing_data_collection       'CrysAlisPro 1.171.39.46 (Rigaku OD, 2018)'
_computing_data_reduction        'CrysAlisPro 1.171.39.46 (Rigaku OD, 2018)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2016/6 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_diffrn_ambient_temperature      296.15
_diffrn_detector_area_resol_mean 16.1827
_diffrn_detector_type            Sapphire3
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_details
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  t~exp~   \w     \q     \k     \f   Frames
--------------------------------------------------------------------------
  1  \w    -49.00  20.00   1.00   60.00    --  -20.36  77.00 -90.00   69
  2  \w    -47.00 -17.00   1.00   60.00    --  -20.36  77.00  90.00   30
  3  \w     17.00  47.00   1.00   60.00    --  -20.36  77.00  90.00   30
  4  \w     19.00  49.00   1.00   60.00    --  -20.36  77.00-180.00   30
  5  \w     59.00  89.00   1.00   60.00    --   21.61  77.00 -90.00   30
  6  \w     -8.00  79.00   1.00   60.00    --   21.61  77.00-180.00   87
  7  \w     -8.00  88.00   1.00   60.00    --   21.61  77.00 -30.00   96
  8  \w      4.00  92.00   1.00   60.00    --   21.61  77.00  60.00   88
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'Xcalibur, Sapphire3'
_diffrn_measurement_method       '\w scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0915
_diffrn_reflns_av_unetI/netI     0.0993
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_number            3405
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_theta_full        24.998
_diffrn_reflns_theta_max         24.998
_diffrn_reflns_theta_min         3.472
_exptl_absorpt_coefficient_mu    0.101
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.15129
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.39.46 (Rigaku Oxford Diffraction, 2018)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.406
_exptl_crystal_description       plate
_exptl_crystal_F_000             196
_exptl_crystal_size_max          0.16
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.04
_refine_diff_density_max         0.301
_refine_diff_density_min         -0.264
_refine_diff_density_rms         0.069
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.964
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     136
_refine_ls_number_reflns         1564
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.964
_refine_ls_R_factor_all          0.1608
_refine_ls_R_factor_gt           0.0860
_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^)+(0.1091P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2055
_refine_ls_wR_factor_ref         0.2733
_reflns_Friedel_coverage         0.000
_reflns_number_gt                649
_reflns_number_total             1564
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            xk5104sup1.cif
_cod_data_source_block           1t
_cod_database_code               2312377
_shelx_shelxl_version_number     2016/6
_shelx_estimated_absorpt_t_max   0.996
_shelx_estimated_absorpt_t_min   0.984
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All N(H) groups, All N(H,H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C7(H7), C2(H2), C5(H5), C3(H3), C4(H4)
;
_shelx_res_checksum              6847
_shelx_hkl_checksum              24986
_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
- Detector area scaling
;
_cod_database_fobs_code 2312377