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_7245997
_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           14
_space_group_name_Hall           '-P 2ybc'
_space_group_name_H-M_alt        'P 1 21/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_audit_creation_date             2020-09-23
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_audit_update_record
;
2022-07-29 deposited with the CCDC.	2022-12-05 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 94.304(4)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   8.0931(3)
_cell_length_b                   14.2729(5)
_cell_length_c                   11.3085(6)
_cell_measurement_reflns_used    2174
_cell_measurement_temperature    293.23(10)
_cell_measurement_theta_max      69.8100
_cell_measurement_theta_min      6.9600
_cell_volume                     1302.58(10)
_computing_cell_refinement       'CrysAlisPro 1.171.38.43f (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.38.43f (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.43f (Rigaku OD, 2015)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXS (Sheldrick, 2008)'
_diffrn_ambient_environment      air
_diffrn_ambient_temperature      293.23(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 16.0733
_diffrn_detector_type            Eos
_diffrn_measured_fraction_theta_full 0.985
_diffrn_measured_fraction_theta_max 0.973
_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     24.00  94.00   1.00    1.00    --   54.00  77.00  60.00   70
  2  \w    105.00 132.00   1.00    1.00    --  108.00 111.00 -30.00   27
  3  \w     92.00 178.00   1.00    1.00    --  108.00  50.00  60.00   86
  4  \w     97.00 167.00   1.00    1.00    --  108.00  63.00 120.00   70
  5  \w     83.00 129.00   1.00    1.00    --  108.00 -63.00  90.00   46
  6  \w     55.00 128.00   1.00    1.00    --  108.00 -63.00 -30.00   73
  7  \w     38.00  64.00   1.00    1.00    --   54.00-126.00 -92.00   26
  8  \w     27.00  88.00   1.00    1.00    --   54.00-125.00   0.00   61
  9  \w     40.00  67.00   1.00    1.00    --  108.00 -63.00  90.00   27
 10  \w     36.00 113.00   1.00    1.00    --  108.00-111.00 -30.00   77
 11  \w     36.00 101.00   1.00    1.00    --  108.00-111.00 -90.00   65
 12  \w     19.00  66.00   1.00    1.00    --    0.00  57.00-150.00   47
 13  \w     14.00  41.00   1.00    1.00    --    0.00  57.00 -30.00   27
 14  \w    -14.00  13.00   1.00    1.00    --    0.00  57.00-150.00   27
 15  \w    -18.00  96.00   1.00    1.00    --   54.00 -19.00-180.00  114
 16  \w    101.00 126.00   1.00    1.00    --  108.00  63.00-180.00   25
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, Eos'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.1065024000
_diffrn_orient_matrix_UB_12      0.0629335000
_diffrn_orient_matrix_UB_13      0.0748718000
_diffrn_orient_matrix_UB_21      -0.0877318000
_diffrn_orient_matrix_UB_22      -0.0873052000
_diffrn_orient_matrix_UB_23      0.0449811000
_diffrn_orient_matrix_UB_31      0.1317082000
_diffrn_orient_matrix_UB_32      -0.0071605000
_diffrn_orient_matrix_UB_33      0.1052954000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0179
_diffrn_reflns_av_unetI/netI     0.0226
_diffrn_reflns_Laue_measured_fraction_full 0.985
_diffrn_reflns_Laue_measured_fraction_max 0.973
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            4653
_diffrn_reflns_point_group_measured_fraction_full 0.985
_diffrn_reflns_point_group_measured_fraction_max 0.973
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         69.532
_diffrn_reflns_theta_min         4.998
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.737
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.54185
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.38.43f (Rigaku Oxford Diffraction, 2015)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            'clear light colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.348
_exptl_crystal_description       block
_exptl_crystal_F_000             552
_exptl_crystal_size_max          0.13
_exptl_crystal_size_mid          0.11
_exptl_crystal_size_min          0.07
_refine_diff_density_max         0.311
_refine_diff_density_min         -0.203
_refine_diff_density_rms         0.039
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.057
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     182
_refine_ls_number_reflns         2378
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.057
_refine_ls_R_factor_all          0.0555
_refine_ls_R_factor_gt           0.0500
_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^)+(0.0814P)^2^+0.3170P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1432
_refine_ls_wR_factor_ref         0.1494
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2069
_reflns_number_total             2378
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d2ce01233b2.cif
_cod_data_source_block           tangy_3
_cod_depositor_comments
'Adding full bibliography for 7245996--7246001.cif.'
_cod_database_code               7245997
_shelx_shelxl_version_number     2018/3
_shelx_estimated_absorpt_t_max   0.950
_shelx_estimated_absorpt_t_min   0.910
_reflns_odcompleteness_completeness 98.36
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All N(H) groups
 At 1.5 times of:
  All O(H) groups
2.a Aromatic/amide H refined with riding coordinates:
 N1(H1), C2(H2A), C4(H4), C5(H5), C6(H6), C7(H7), C9(H9), C10(H10), C13(H13),
 C14(H14), C15(H15)
2.b Idealised tetrahedral OH refined as rotating group:
 O2(H2)
;
_shelx_res_checksum              9493
_shelx_hkl_checksum              52462
_olex2_date_sample_data_collection 2020-09-16
_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
;
_oxdiff_exptl_absorpt_empirical_full_max 2.484
_oxdiff_exptl_absorpt_empirical_full_min 0.502