π–π stacking in the polymorphism of 2-(naphthalenylamino)-nicotinic acids and a comparison with their analogues
Li, Yuping; Tao, Yang; Zhoujin, Yunping; Zhao, Fang; Liang, Peng-Yu; Parkin, Sean; Li, Tonglei; Zhou, Pan-Pan; Long, Sihui; CrystEngComm 25 (2023) 432–443; doi:10.1039/D2CE01233B

data_7246001
_publ_section_title
;
 \p--\p stacking in the polymorphism of 2-(naphthalenylamino)-nicotinic
 acids and a comparison with their analogues
;
_journal_issue                   3
_journal_name_full               CrystEngComm
_journal_page_first              432
_journal_page_last               443
_journal_paper_doi               10.1039/D2CE01233B
_journal_volume                  25
_journal_year                    2023
_chemical_formula_moiety         'C16 H12 N2 O2'
_chemical_formula_sum            'C16 H12 N2 O2'
_chemical_formula_weight         264.28
_space_group_crystal_system      monoclinic
_space_group_IT_number           15
_space_group_name_Hall           '-C 2yc'
_space_group_name_H-M_alt        'C 1 2/c 1'
_atom_sites_solution_hydrogens   difmap
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-2018/3
_audit_update_record
;
2022-07-29 deposited with the CCDC.	2022-12-05 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 107.503(6)
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   19.3362(12)
_cell_length_b                   10.0456(6)
_cell_length_c                   14.1500(7)
_cell_measurement_reflns_used    1808
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      69.9100
_cell_measurement_theta_min      8.8150
_cell_volume                     2621.3(3)
_computing_cell_refinement       '<i>APEX3</i> (Bruker-AXS, 2016)'
_computing_data_collection       '<i>APEX3</i> (Bruker-AXS, 2016)'
_computing_data_reduction        '<i>APEX3</i> (Bruker-AXS, 2016)'
_computing_molecular_graphics    '<i>XP in SHELXTL</i> (Sheldrick, 2008)'
_computing_publication_material
'<i>SHELX</i> (Sheldrick, 2008) and <i>CIFFIX</i> (Parkin, 2013)'
_computing_structure_refinement  '<i>SHELXL-2018/3</i> (Sheldrick, 2015b)'
_computing_structure_solution    '<i>SHELXT</i> (Sheldrick, 2015a)'
_diffrn_ambient_temperature      293(2)
_diffrn_detector_area_resol_mean 7.41
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.983
_diffrn_measurement_device_type  'Bruker D8 Venture dual source'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0215
_diffrn_reflns_av_unetI/netI     0.0270
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.983
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_h_min       -23
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            4848
_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.983
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         69.725
_diffrn_reflns_theta_min         4.796
_diffrn_source                   microsource
_exptl_absorpt_coefficient_mu    0.733
_exptl_absorpt_correction_T_max  0.000
_exptl_absorpt_correction_T_min  0.000
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '<i>SADABS</i> (Krause et al., 2015)'
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.339
_exptl_crystal_description       slab
_exptl_crystal_F_000             1104
_exptl_crystal_size_max          0.090
_exptl_crystal_size_mid          0.050
_exptl_crystal_size_min          0.030
_refine_diff_density_max         0.140
_refine_diff_density_min         -0.143
_refine_diff_density_rms         0.028
_refine_ls_extinction_coef       0.0007(2)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2018/3 (Sheldrick 2018)'
_refine_ls_goodness_of_fit_ref   1.041
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     278
_refine_ls_number_reflns         2441
_refine_ls_number_restraints     196
_refine_ls_restrained_S_all      1.005
_refine_ls_R_factor_all          0.0557
_refine_ls_R_factor_gt           0.0433
_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^)+(0.0653P)^2^+0.4678P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1168
_refine_ls_wR_factor_ref         0.1316
_reflns_Friedel_coverage         0.000
_reflns_number_gt                1899
_reflns_number_total             2441
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d2ce01233b2.cif
_cod_data_source_block           taoyang_4
_cod_depositor_comments
'Adding full bibliography for 7245996--7246001.cif.'
_cod_original_sg_symbol_H-M      'C 2/c'
_cod_database_code               7246001
_shelx_shelxl_version_number     2018/3
_shelx_estimated_absorpt_t_min   0.937
_shelx_estimated_absorpt_t_max   0.978
_exptl_absorpt_special_details
; 
In addition to absorption, multi-scan techniques also correct other slowly 
varying changes in scale factor over reciprocal space, such as those caused 
by X-ray beam inhomogeneity, goniometer imperfection, crystal decomposition, 
crystal longer than the X-ray beam cross section, absorption by the crystal 
mount etc.  These account, by and large, for much of the difference between 
estimated values of Tmin and Tmax and the _exptl_absorpt_correction_ values. 
;
_shelx_res_checksum              78702
_shelx_hkl_checksum              21856