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_7245996
_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
_atom_sites_solution_secondary   difmap
_audit_creation_date             2020-10-27
_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                90.00
_cell_angle_beta                 96.386(11)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   3.9181(6)
_cell_length_b                   24.592(3)
_cell_length_c                   13.0589(12)
_cell_measurement_reflns_used    895
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      67.0120
_cell_measurement_theta_min      6.3560
_cell_volume                     1250.5(3)
_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_temperature      293(2)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 16.0733
_diffrn_detector_type            Eos
_diffrn_measured_fraction_theta_full 0.973
_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     44.00  77.00   1.50    3.00    --   54.00  57.00  60.00   22
  2  \w     86.00 122.00   1.50    3.00    --   54.00  57.00  60.00   24
  3  \w    101.00 131.00   1.50    4.00    --  108.00  63.00  60.00   20
  4  \w    118.00 176.50   1.50    4.00    --  108.00 111.00   0.00   39
  5  \w    121.00 161.50   1.50    4.00    --  108.00  50.00   0.00   27
  6  \w    104.00 129.50   1.50    4.00    --  108.00 -50.00 120.00   17
  7  \w     88.00 115.00   1.50    4.00    --  108.00-111.00  30.00   18
  8  \w     44.00  71.00   1.50    4.00    --  108.00-111.00  30.00   18
  9  \w     24.00  90.00   1.50    3.00    --   54.00-125.00  30.00   44
 10  \w     39.00  91.50   1.50    4.00    --  108.00-111.00 150.00   35
 11  \w     90.00 174.00   1.50    4.00    --  108.00  63.00 150.00   56
 12  \w     60.00 150.00   1.50    4.00    --  108.00 178.00  60.00   60
 13  \w     50.00 122.00   1.50    3.00    --   54.00  57.00-180.00   48
 14  \w    104.00 170.00   1.50    4.00    --  108.00 111.00-180.00   44
 15  \w     17.00  62.00   1.50    3.00    --   54.00 -57.00-180.00   30
 16  \w    -42.00 -16.50   1.50    1.50    --    0.00 -57.00 120.00   17
;
_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      -0.0915045000
_diffrn_orient_matrix_UB_12      0.0601025000
_diffrn_orient_matrix_UB_13      0.0154633000
_diffrn_orient_matrix_UB_21      -0.3224565000
_diffrn_orient_matrix_UB_22      -0.0175097000
_diffrn_orient_matrix_UB_23      0.0491490000
_diffrn_orient_matrix_UB_31      0.2107825000
_diffrn_orient_matrix_UB_32      -0.0006180000
_diffrn_orient_matrix_UB_33      0.1069397000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0323
_diffrn_reflns_av_unetI/netI     0.0468
_diffrn_reflns_limit_h_max       4
_diffrn_reflns_limit_h_min       -4
_diffrn_reflns_limit_k_max       29
_diffrn_reflns_limit_k_min       -28
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            4462
_diffrn_reflns_theta_full        70.16
_diffrn_reflns_theta_max         70.16
_diffrn_reflns_theta_min         3.59
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.768
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.96584
_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 yellow'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.404
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             552
_exptl_crystal_size_max          0.08
_exptl_crystal_size_mid          0.07
_exptl_crystal_size_min          0.01
_refine_diff_density_max         0.164
_refine_diff_density_min         -0.226
_refine_diff_density_rms         0.048
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.058
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     181
_refine_ls_number_reflns         2317
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.058
_refine_ls_R_factor_all          0.0706
_refine_ls_R_factor_gt           0.0497
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0574P)^2^+0.1351P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1209
_refine_ls_wR_factor_ref         0.1407
_reflns_number_gt                1663
_reflns_number_total             2317
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            d2ce01233b2.cif
_cod_data_source_block           taoyang_11
_cod_depositor_comments
'Adding full bibliography for 7245996--7246001.cif.'
_cod_database_code               7245996
_reflns_odcompleteness_completeness 99.74
_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
2.a Aromatic/amide H refined with riding coordinates:
 N1(H1), N2(H2), C3(H3), C4(H4), C5(H5), C8(H8), C9(H9), C10(H10), C12(H12),
 C13(H13), C14(H14), C15(H15)
;
_olex2_date_sample_data_collection 2020-10-27
_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 1.260
_oxdiff_exptl_absorpt_empirical_full_min 0.765