#------------------------------------------------------------------------------
#$Date: 2023-05-05 03:26:53 +0300 (Fri, 05 May 2023) $
#$Revision: 283096 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/13/14/7131465.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/
#
# All data on this site have been placed in the public domain by the
# contributors.
#
data_7131465
loop_
_publ_author_name
'Li, Jie'
'Zhang, Tie'
'Lun, Meng-Meng'
'Su, Chang-Yuan'
'Zhang, Zhi-Xu'
'Huang, Pei-Zhi'
'Zhang, Yi'
'Teri, Gele'
'Fu, Da-Wei'
_publ_section_title
;
 Nicotinic acid bromide: a simple organic salt optical-electrical
 ferroelastic with high Tc.
;
_journal_issue                   31
_journal_name_full               'Chemical communications (Cambridge, England)'
_journal_page_first              4644
_journal_page_last               4647
_journal_paper_doi               10.1039/d3cc00776f
_journal_volume                  59
_journal_year                    2023
_chemical_formula_moiety         'Cl, C6 H6 N O2'
_chemical_formula_sum            'C6 H6 Cl N O2'
_chemical_formula_weight         159.57
_space_group_crystal_system      monoclinic
_space_group_IT_number           11
_space_group_name_Hall           '-P 2yb'
_space_group_name_H-M_alt        'P 1 21/m 1'
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     dual
_audit_creation_date             2023-03-20
_audit_creation_method
;
Olex2 1.3
(compiled 2020.11.12 svn.r5f609507 for OlexSys, GUI svn.r6272)
;
_audit_update_record
;
2023-03-21 deposited with the CCDC.	2023-03-22 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 99.545(4)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   7.1749(3)
_cell_length_b                   6.6728(3)
_cell_length_c                   7.4888(3)
_cell_measurement_reflns_used    6064
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      30.6760
_cell_measurement_theta_min      2.7330
_cell_volume                     353.58(3)
_computing_cell_refinement       'CrysAlisPro 1.171.42.84a (Rigaku OD, 2023)'
_computing_data_collection       'CrysAlisPro 1.171.42.84a (Rigaku OD, 2023)'
_computing_data_reduction        'CrysAlisPro 1.171.42.84a (Rigaku OD, 2023)'
_computing_molecular_graphics    'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_diffrn_ambient_temperature      293(2)
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            HyPix
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measurement_details
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω     -8.00  76.00   0.50    0.50    --    4.83  77.00  60.00  168
  2  ω     12.00  77.00   0.50    0.50    --    4.83  58.00 -53.00  130
  3  ω     -9.00  18.00   0.50    0.50    --    4.83 -38.00  30.00   54
  4  ω    -48.00 -23.00   0.50    0.50    --    4.83 -58.00 165.00   50
  5  ω    -42.00  18.00   0.50    0.50    --    4.83 -31.00 120.39  120
  6  ω    -64.00  18.00   0.50    0.50    --    4.83 -19.00  60.00  164
  7  ω    -68.00  17.00   0.50    0.50    --    4.83 -19.00 -30.00  170
  8  ω    -61.00  18.00   0.50    0.50    --    4.83 -19.00-180.00  158
  9  ω    -18.00  61.00   0.50    0.50    --   -5.53  19.00 -90.00  158
 10  ω    -19.00  62.00   0.50    0.50    --   -5.53  58.00 -53.00  162
 11  ω    -56.00 -22.00   0.50    0.50    --   -5.53 -58.00 165.00   68
 12  ω     18.00  48.00   0.50    0.50    --    4.83-120.00 148.55   60
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB Synergy R, DW system, HyPix'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0468791000
_diffrn_orient_matrix_UB_12      0.0794461000
_diffrn_orient_matrix_UB_13      -0.0372134000
_diffrn_orient_matrix_UB_21      0.0393517000
_diffrn_orient_matrix_UB_22      -0.0695283000
_diffrn_orient_matrix_UB_23      -0.0550139000
_diffrn_orient_matrix_UB_31      -0.0794069000
_diffrn_orient_matrix_UB_32      0.0124325000
_diffrn_orient_matrix_UB_33      -0.0693576000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0285
_diffrn_reflns_av_unetI/netI     0.0137
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.995
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       9
_diffrn_reflns_limit_l_min       -9
_diffrn_reflns_number            9039
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.995
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         28.280
_diffrn_reflns_theta_min         2.758
_diffrn_source                   'Rotating-anode X-ray tube'
_diffrn_source_type              'Rigaku (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    0.473
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.85071
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.42.84a (Rigaku Oxford Diffraction, 2023)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.499
_exptl_crystal_description       block
_exptl_crystal_F_000             164
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.1
_refine_diff_density_max         0.315
_refine_diff_density_min         -0.163
_refine_diff_density_rms         0.040
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.093
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     67
_refine_ls_number_reflns         943
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.093
_refine_ls_R_factor_all          0.0316
_refine_ls_R_factor_gt           0.0288
_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/[σ²(Fo²)+(0.0382P)²+0.1000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0792
_refine_ls_wR_factor_ref         0.0809
_reflns_Friedel_coverage         0.000
_reflns_number_gt                854
_reflns_number_total             943
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d3cc00776f3.cif
_cod_data_source_block           n_c_1_auto_r
_cod_depositor_comments
'Adding full bibliography for 7131465--7131468.cif.'
_cod_database_code               7131465
_shelx_shelxl_version_number     2018/3
_chemical_oxdiff_formula         'C1 H1 N1 O1 Cl1'
_shelx_space_group_comment
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_shelx_estimated_absorpt_t_max   0.954
_shelx_estimated_absorpt_t_min   0.911
_reflns_odcompleteness_completeness 99.47
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     28.22
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C1(H1B), C2(H2), C3(H3), C5(H5)
;
_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 1.361
_oxdiff_exptl_absorpt_empirical_full_min 0.810
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z'
'-x, -y, -z'
'x, -y-1/2, z'
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Cl1 Cl 0.28102(6) 0.250000 0.85217(6) 0.04112(17) Uani 1 2 d S T P . .
O1 O 0.4449(2) 0.250000 0.52082(18) 0.0533(4) Uani 1 2 d S T P . .
H1 H 0.392(5) 0.250000 0.634(5) 0.091(10) Uiso 1 2 d S . P . .
N1 N 0.7124(2) 0.250000 0.0824(2) 0.0376(4) Uani 1 2 d S T P . .
H1A H 0.640(4) 0.250000 -0.022(3) 0.053(7) Uiso 1 2 d S . P . .
C1 C 0.8991(3) 0.250000 0.0984(3) 0.0454(5) Uani 1 2 d S T P . .
H1B H 0.956289 0.250000 -0.004348 0.055 Uiso 1 2 calc R U P . .
C2 C 1.0076(3) 0.250000 0.2674(3) 0.0518(6) Uani 1 2 d S T P . .
H2 H 1.138755 0.250000 0.280025 0.062 Uiso 1 2 calc R U P . .
O2 O 0.7182(2) 0.250000 0.70926(19) 0.0784(7) Uani 1 2 d S T P . .
C3 C 0.9204(3) 0.250000 0.4188(3) 0.0449(5) Uani 1 2 d S T P . .
H3 H 0.992227 0.250000 0.534225 0.054 Uiso 1 2 calc R U P . .
C4 C 0.7252(3) 0.250000 0.3967(2) 0.0360(4) Uani 1 2 d S T P . .
C5 C 0.6220(3) 0.250000 0.2244(2) 0.0364(4) Uani 1 2 d S T P . .
H5 H 0.490584 0.250000 0.207161 0.044 Uiso 1 2 calc R U P . .
C6 C 0.6293(3) 0.250000 0.5594(2) 0.0428(4) Uani 1 2 d S T P . .
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C6 O1 H1 109(2) . . ?
C1 N1 H1A 122.0(17) . . ?
C1 N1 C5 123.08(16) . . ?
C5 N1 H1A 114.9(17) . . ?
N1 C1 H1B 120.2 . . ?
N1 C1 C2 119.61(17) . . ?
C2 C1 H1B 120.2 . . ?
C1 C2 H2 120.3 . . ?
C1 C2 C3 119.47(18) . . ?
C3 C2 H2 120.3 . . ?
C2 C3 H3 120.4 . . ?
C4 C3 C2 119.25(17) . . ?
C4 C3 H3 120.4 . . ?
C3 C4 C6 119.74(16) . . ?
C5 C4 C3 119.27(16) . . ?
C5 C4 C6 120.99(17) . . ?
N1 C5 C4 119.32(17) . . ?
N1 C5 H5 120.3 . . ?
C4 C5 H5 120.3 . . ?
O1 C6 C4 113.93(16) . . ?
O2 C6 O1 124.79(17) . . ?
O2 C6 C4 121.27(18) . . ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O1 H1 0.98(4) . ?
O1 C6 1.307(2) . ?
N1 H1A 0.87(3) . ?
N1 C1 1.326(3) . ?
N1 C5 1.334(2) . ?
C1 H1B 0.9300 . ?
C1 C2 1.371(3) . ?
C2 H2 0.9300 . ?
C2 C3 1.383(3) . ?
O2 C6 1.195(2) . ?
C3 H3 0.9300 . ?
C3 C4 1.383(3) . ?
C4 C5 1.377(2) . ?
C4 C6 1.495(2) . ?
C5 H5 0.9300 . ?
loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
N1 C1 C2 C3 0.000(0) . . . . ?
C1 N1 C5 C4 0.000(0) . . . . ?
C1 C2 C3 C4 0.000(0) . . . . ?
C2 C3 C4 C5 0.000(0) . . . . ?
C2 C3 C4 C6 180.000(0) . . . . ?
C3 C4 C5 N1 0.000(0) . . . . ?
C3 C4 C6 O1 180.000(0) . . . . ?
C3 C4 C6 O2 0.000(0) . . . . ?
C5 N1 C1 C2 0.000(0) . . . . ?
C5 C4 C6 O1 0.000(0) . . . . ?
C5 C4 C6 O2 180.000(0) . . . . ?
C6 C4 C5 N1 180.000(0) . . . . ?
