Hydrogen bonding vs stacking interaction in the crystals of the simplest coumarin derivatives: study from the energetic viewpoint
Shishkina, Svitlana V.; Konovalova, Irina S.; Kovalenko, Sergiy Mykolayovich; Trostianko , Pavlo V.; Geleverya, Anna O.; Bunyatyan, Natalya D.; CrystEngComm  (2019) –; doi:10.1039/C9CE01344J

data_7234392
_publ_section_title
;
 Hydrogen bonding vs stacking interaction in the crystals of the simplest
 coumarin derivatives: study from the energetic viewpoint
;
_journal_name_full               CrystEngComm
_journal_paper_doi               10.1039/C9CE01344J
_journal_year                    2019
_chemical_formula_sum            'C10 H8 N2 O2'
_chemical_formula_weight         188.18
_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-2016/6
_audit_update_record
;
2019-08-23 deposited with the CCDC.    2019-10-04 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 93.970(14)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   4.7260(9)
_cell_length_b                   14.633(3)
_cell_length_c                   12.5056(17)
_cell_measurement_reflns_used    402
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      20.613
_cell_measurement_theta_min      4.279
_cell_volume                     862.8(3)
_computing_structure_refinement  'SHELXL-2016/6 (Sheldrick, 2016)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_diffrn_ambient_temperature      293(2)
_diffrn_detector_area_resol_mean 16.1827
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_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  0.1083
_diffrn_reflns_av_unetI/netI     0.1236
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_k_max       19
_diffrn_reflns_limit_k_min       -20
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            8503
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         29.996
_diffrn_reflns_theta_min         3.228
_diffrn_source                   'Enhance (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    0.104
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.32968
_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            colorless
_exptl_crystal_density_diffrn    1.449
_exptl_crystal_description       stick
_exptl_crystal_F_000             392
_exptl_crystal_size_max          0.200
_exptl_crystal_size_mid          0.040
_exptl_crystal_size_min          0.040
_refine_diff_density_max         0.464
_refine_diff_density_min         -0.228
_refine_diff_density_rms         0.069
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.874
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     127
_refine_ls_number_reflns         2528
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.874
_refine_ls_R_factor_all          0.2195
_refine_ls_R_factor_gt           0.0879
_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^)+(0.1074P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2096
_refine_ls_wR_factor_ref         0.2744
_reflns_Friedel_coverage         0.000
_reflns_number_gt                804
_reflns_number_total             2528
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c9ce01344j2.cif
_cod_data_source_block           on
_cod_original_cell_volume        862.7(3)
_cod_database_code               7234392
_shelx_shelxl_version_number     2016/6
_shelx_estimated_absorpt_t_min   0.980
_shelx_estimated_absorpt_t_max   0.996
_shelx_res_checksum              19252