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_7246000
_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         'C14 H14 N2 O2'
_chemical_formula_sum            'C14 H14 N2 O2'
_chemical_formula_weight         242.27
_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     dual
_audit_creation_date             2021-07-25
_audit_creation_method
;
Olex2 1.3-ac4
(compiled 2019.04.23 svn.r3594 for Rigaku Oxford Diffraction, GUI svn.r5739)
;
_audit_update_record
;
2022-07-29 deposited with the CCDC.	2022-12-05 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 93.896(2)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   6.81390(10)
_cell_length_b                   24.3841(5)
_cell_length_c                   7.44210(10)
_cell_measurement_reflns_used    6074
_cell_measurement_temperature    300.42(10)
_cell_measurement_theta_max      77.0590
_cell_measurement_theta_min      6.2330
_cell_volume                     1233.65(4)
_computing_cell_refinement       'CrysAlisPro 1.171.41.103a (Rigaku OD, 2021)'
_computing_data_collection       'CrysAlisPro 1.171.41.103a (Rigaku OD, 2021)'
_computing_data_reduction        'CrysAlisPro 1.171.41.103a (Rigaku OD, 2021)'
_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    'ShelXT (Sheldrick, 2015)'
_diffrn_ambient_environment      air
_diffrn_ambient_temperature      300.42(10)
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            HyPix
_diffrn_measured_fraction_theta_full 0.994
_diffrn_measured_fraction_theta_max 0.937
_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     99.00 170.00   0.50    0.05    --  107.75  57.00 -30.00  142
  2  \w    115.00 175.00   0.50    0.05    --  107.75  57.00  30.00  120
  3  \w     96.00 158.00   0.50    0.05    --  107.75  37.00  30.00  124
  4  \w     30.00  55.00   0.50    0.05    --   47.57-121.00 -37.00   50
  5  \w     72.00  97.00   0.50    0.05    --  107.75-121.00 -37.00   50
  6  \w     52.00  78.00   0.50    0.05    --  107.75 -99.00   0.00   52
  7  \w     46.00  71.00   0.50    0.05    --   47.57-151.00 161.00   50
  8  \w     58.00  83.00   0.50    0.05    --  107.75-151.00 161.00   50
  9  \w     35.00  60.00   0.50    0.05    --  107.75 -57.00  30.00   50
 10  \w    -26.00  23.00   0.50    0.05    --   47.57 -19.00 120.00   98
 11  \w    -25.00  18.00   0.50    0.05    --   47.57 -19.00  60.00   86
 12  \w    -22.00  22.00   0.50    0.05    --   47.57 -19.00-180.00   88
 13  \w     82.00 144.00   0.50    0.05    --  107.75 121.00  44.00  124
 14  \w     62.00  92.00   0.50    0.05    --   47.57 151.00-154.00   60
 15  \w    101.00 126.00   0.50    0.05    --  107.75 151.00-154.00   50
 16  \w   -107.00 -82.00   0.50    0.05    -- -100.00 151.00-154.00   50
 17  \w   -119.00 -53.00   0.50    0.05    -- -100.00 135.00 -30.11  132
 18  \w    -83.00 -56.00   0.50    0.05    --  -47.57 121.00  44.00   54
 19  \w   -103.00 -51.00   0.50    0.05    -- -100.00 121.00  44.00  104
 20  \w   -109.00 -27.00   0.50    0.05    -- -100.00  77.00  60.00  164
 21  \w    -68.00 -39.00   0.50    0.05    -- -100.00  57.00   0.00   58
 22  \w    -59.00 -28.00   0.50    0.05    -- -100.00  57.00 -90.00   62
 23  \w    -29.00   0.00   0.50    0.05    --  -47.57  19.00-180.00   58
 24  \w    -68.00 -38.00   0.50    0.05    -- -100.00  57.00-120.00   60
 25  \w   -129.00-104.00   0.50    0.05    -- -100.00-121.00 -37.00   50
 26  \w    -96.00 -68.00   0.50    0.05    --  -47.57-151.00 161.00   56
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'ROD, Synergy Custom system, HyPix'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0147199000
_diffrn_orient_matrix_UB_12      -0.0626892000
_diffrn_orient_matrix_UB_13      0.0228213000
_diffrn_orient_matrix_UB_21      0.1084031000
_diffrn_orient_matrix_UB_22      -0.0039399000
_diffrn_orient_matrix_UB_23      -0.1745572000
_diffrn_orient_matrix_UB_31      0.1984694000
_diffrn_orient_matrix_UB_32      0.0067765000
_diffrn_orient_matrix_UB_33      0.1098182000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0205
_diffrn_reflns_av_unetI/netI     0.0180
_diffrn_reflns_Laue_measured_fraction_full 0.994
_diffrn_reflns_Laue_measured_fraction_max 0.937
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       30
_diffrn_reflns_limit_k_min       -26
_diffrn_reflns_limit_l_max       9
_diffrn_reflns_limit_l_min       -8
_diffrn_reflns_number            8468
_diffrn_reflns_point_group_measured_fraction_full 0.994
_diffrn_reflns_point_group_measured_fraction_max 0.937
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         77.359
_diffrn_reflns_theta_min         6.231
_diffrn_source                   'Rotating-anode X-ray tube'
_diffrn_source_type              'Rigaku (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.720
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.69597
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.41.103a (Rigaku Oxford Diffraction, 2021)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            'clear light yellow'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.304
_exptl_crystal_description       plate
_exptl_crystal_F_000             512
_exptl_crystal_size_max          0.12
_exptl_crystal_size_mid          0.05
_exptl_crystal_size_min          0.03
_refine_diff_density_max         0.193
_refine_diff_density_min         -0.135
_refine_diff_density_rms         0.030
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.096
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     166
_refine_ls_number_reflns         2458
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.096
_refine_ls_R_factor_all          0.0438
_refine_ls_R_factor_gt           0.0397
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0685P)^2^+0.1114P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1167
_refine_ls_wR_factor_ref         0.1203
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2136
_reflns_number_total             2458
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d2ce01233b2.cif
_cod_data_source_block           taoya-6-2_auto
_cod_depositor_comments
'Adding full bibliography for 7245996--7246001.cif.'
_cod_database_code               7246000
_shelx_shelxl_version_number     2018/3
_shelx_estimated_absorpt_t_max   0.979
_shelx_estimated_absorpt_t_min   0.919
_reflns_odcompleteness_completeness 99.52
_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 C(H,H,H) groups, All O(H) groups
2.a Aromatic/amide H refined with riding coordinates:
 N2(H2A), C3(H3), C4(H4), C5(H5), C8(H8), C11(H11), C12(H12)
2.b Idealised Me refined as rotating group:
 C13(H13A,H13B,H13C), C14(H14A,H14B,H14C)
2.c Idealised tetrahedral OH refined as rotating group:
 O2(H2)
;
_shelx_res_checksum              47177
_shelx_hkl_checksum              77049
_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 1.547
_oxdiff_exptl_absorpt_empirical_full_min 0.698