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_7245999
_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, H2 O'
_chemical_formula_sum            'C16 H14 N2 O3'
_chemical_formula_weight         282.29
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -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                75.646(14)
_cell_angle_beta                 83.673(13)
_cell_angle_gamma                79.935(14)
_cell_formula_units_Z            4
_cell_length_a                   7.4767(12)
_cell_length_b                   10.7575(17)
_cell_length_c                   17.909(3)
_cell_measurement_reflns_used    1213
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      61.3120
_cell_measurement_theta_min      5.5060
_cell_volume                     1370.6(4)
_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 0.966
_diffrn_measured_fraction_theta_max 0.966
_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     35.00 110.00   1.50    1.50    --   54.00-134.00 126.00   50
  2  \w    106.00 136.00   1.50    2.00    --  108.00 -91.00  90.00   20
  3  \w     71.00 116.00   1.50    2.00    --  108.00-111.00   0.00   30
  4  \w    110.00 137.00   1.50    2.00    --  108.00 -91.00 -60.00   18
  5  \w     59.00  93.50   1.50    2.00    --  108.00 -91.00  90.00   23
  6  \w     47.00 108.50   1.50    2.00    --  108.00-111.00 150.00   41
  7  \w     39.00 141.00   1.50    2.00    --  108.00 -25.00  60.00   68
  8  \w     90.00 126.00   1.50    2.00    --  108.00  38.00 120.00   24
  9  \w     76.00 178.00   1.50    2.00    --  108.00  25.00  60.00   68
 10  \w    116.00 143.00   1.50    2.00    --  108.00 111.00   0.00   18
 11  \w    106.00 169.00   1.50    2.00    --  108.00 135.00  12.00   42
 12  \w     85.00 160.00   1.50    2.00    --  108.00  25.00 -30.00   50
 13  \w     54.00  87.00   1.50    2.00    --  108.00 -91.00 -60.00   22
 14  \w     42.00 123.00   1.50    2.00    --  108.00 -50.00 -30.00   54
 15  \w     50.00  77.00   1.50    1.50    --   54.00 -38.00 -90.00   18
 16  \w     38.00 129.50   1.50    2.00    --  108.00 -50.00-120.00   61
 17  \w     45.00  72.00   1.50    1.50    --   54.00-125.00-180.00   18
 18  \w     12.00  72.00   1.50    1.50    --   54.00 -57.00 -90.00   40
 19  \w      4.00  95.50   1.50    1.50    --   54.00 -19.00 -30.00   61
 20  \w     41.00  68.00   1.50    1.50    --    0.00  77.00 -30.00   18
 21  \w     40.00 112.00   1.50    2.00    --  108.00 -50.00 120.00   48
 22  \w     39.00 111.00   1.50    1.50    --   54.00  57.00 150.00   48
 23  \w    -18.00   7.50   1.50    1.50    --   54.00 -38.00 -90.00   17
 24  \w    -12.00  69.00   1.50    1.50    --   54.00 -57.00-180.00   54
 25  \w    -21.00  15.00   1.50    1.50    --    0.00  77.00 -30.00   24
 26  \w    -61.00 -34.00   1.50    1.50    --    0.00 -57.00-150.00   18
 27  \w    -26.00   1.00   1.50    1.50    --    0.00 -57.00-150.00   18
;
_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      -0.0206615000
_diffrn_orient_matrix_UB_12      0.0795616000
_diffrn_orient_matrix_UB_13      -0.0837255000
_diffrn_orient_matrix_UB_21      -0.1020359000
_diffrn_orient_matrix_UB_22      0.1171213000
_diffrn_orient_matrix_UB_23      0.0302150000
_diffrn_orient_matrix_UB_31      0.1821312000
_diffrn_orient_matrix_UB_32      0.0482563000
_diffrn_orient_matrix_UB_33      0.0002410000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0363
_diffrn_reflns_av_unetI/netI     0.0643
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            8684
_diffrn_reflns_theta_full        70.42
_diffrn_reflns_theta_max         70.42
_diffrn_reflns_theta_min         4.29
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.790
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.94883
_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    1.368
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             592
_exptl_crystal_size_max          0.08
_exptl_crystal_size_mid          0.05
_exptl_crystal_size_min          0.02
_refine_diff_density_max         0.224
_refine_diff_density_min         -0.237
_refine_diff_density_rms         0.048
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.005
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     387
_refine_ls_number_reflns         5056
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.005
_refine_ls_R_factor_all          0.1069
_refine_ls_R_factor_gt           0.0567
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0566P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1323
_refine_ls_wR_factor_ref         0.1740
_reflns_number_gt                2795
_reflns_number_total             5056
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            d2ce01233b2.cif
_cod_data_source_block           taoy_10
_cod_depositor_comments
;
Adding full bibliography for 7245996--7246001.cif.

2024-06-28
Z value and formula fixed to values more according to usual
chemical conventions.                 miguel
;
_cod_original_formula_sum            'C32 H28 N4 O6'
_cod_original_formula_weight         564.58
_cod_original_formula_moiety         '2(C16 H12 N2 O2), 2(H2 O)'
_cod_original_formula_units_Z            2
_cod_database_code               7245999
_reflns_odcompleteness_completeness 99.61
_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, All O(H,H) groups
2.a Free rotating group:
 O3(H3A,H3B), O6(H6A,H6B)
2.b Aromatic/amide H refined with riding coordinates:
 N2(H2A), C3(H3), C4(H4), C5(H5), C8(H8), C9(H9), C10(H10), C12(H12), C13(H13),
  C14(H14), C15(H15), N4(H4A), C19(H19), C20(H20), C21(H21), C24(H24), C25(H25),
  C26(H26), C28(H28), C29(H29), C30(H30), C31(H31)
2.c Idealised tetrahedral OH refined as rotating group:
 O2(H2), O5(H5A)
;
_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 1.647
_oxdiff_exptl_absorpt_empirical_full_min 0.735