#------------------------------------------------------------------------------
#$Date: 2025-04-03 08:32:21 +0300 (Thu, 03 Apr 2025) $
#$Revision: 298703 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/13/14/7131468.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_7131468
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         'I, C6 H6 N O2'
_chemical_formula_sum            'C6 H6 N O2 I'
_chemical_formula_weight         251.02
_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   mixed
_atom_sites_solution_primary     direct
_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                81.904(7)
_cell_angle_beta                 79.902(6)
_cell_angle_gamma                67.021(7)
_cell_formula_units_Z            2
_cell_length_a                   7.4174(5)
_cell_length_b                   7.4195(7)
_cell_length_c                   8.1011(7)
_cell_measurement_reflns_used    7449
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      31.1040
_cell_measurement_theta_min      2.5330
_cell_volume                     402.80(6)
_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    'SHELXS  (Sheldrick, 2008)'
_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 0.992
_diffrn_measurement_details
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -26.00  -1.00   0.50    0.50    --    4.98 -88.00 -49.00   50
  2  ω    -31.00   1.00   0.50    0.50    --   -5.77 -88.00 -49.00   64
  3  ω    -20.00   7.00   0.50    0.50    --   -5.77  33.00 -35.92   54
  4  ω     38.00  63.00   0.50    0.50    --   -5.77  33.00 -35.92   50
  5  ω      6.00  42.00   0.50    0.50    --   -5.77  88.00  66.00   72
  6  ω    -22.00  38.00   0.50    0.50    --    4.98  88.00  66.00  120
  7  ω     -9.00  77.00   0.50    0.50    --    4.98  57.00-120.00  172
  8  ω    -10.00  17.00   0.50    0.50    --    4.98 -38.00-120.00   54
  9  ω    -64.00 -12.00   0.50    0.50    --    4.98 -38.00-120.00  104
 10  ω    -58.00 -31.00   0.50    0.50    --    4.98 -19.00-180.00   54
 11  ω    -26.00  17.00   0.50    0.50    --    4.98 -19.00-180.00   86
 12  ω    -63.00  18.00   0.50    0.50    --    4.98 -19.00 -90.00  162
 13  ω    -70.00  18.00   0.50    0.50    --    4.98 -19.00   0.00  176
 14  ω    -70.00  18.00   0.50    0.50    --    4.98 -19.00  90.00  176
 15  ω    -42.00  18.00   0.50    0.50    --    4.98 -31.00 145.67  120
;
_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      -0.0091877000
_diffrn_orient_matrix_UB_12      -0.0523324000
_diffrn_orient_matrix_UB_13      0.0792951000
_diffrn_orient_matrix_UB_21      -0.1027455000
_diffrn_orient_matrix_UB_22      0.0570348000
_diffrn_orient_matrix_UB_23      0.0119334000
_diffrn_orient_matrix_UB_31      -0.0184134000
_diffrn_orient_matrix_UB_32      -0.0697152000
_diffrn_orient_matrix_UB_33      -0.0391133000
_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  0.0375
_diffrn_reflns_av_unetI/netI     0.0201
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.992
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_number            9155
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.992
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.875
_diffrn_reflns_theta_min         2.562
_diffrn_source                   'Rotating-anode X-ray tube'
_diffrn_source_type              'Rigaku (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    3.916
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.28863
_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            'light yellow'
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    2.070
_exptl_crystal_description       block
_exptl_crystal_F_000             236
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.18
_exptl_crystal_size_min          0.15
_refine_diff_density_max         1.501
_refine_diff_density_min         -1.445
_refine_diff_density_rms         0.143
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.096
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     96
_refine_ls_number_reflns         1903
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.096
_refine_ls_R_factor_all          0.0383
_refine_ls_R_factor_gt           0.0358
_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)+(0.0525P)²+0.6000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0899
_refine_ls_wR_factor_ref         0.0910
_reflns_Friedel_coverage         0.000
_reflns_number_gt                1785
_reflns_number_total             1903
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d3cc00776f3.cif
_cod_data_source_block           n_i_sphere_auto-r
_cod_depositor_comments
;
Adding full bibliography for 7131465--7131468.cif.

2025-03-31
Z value and formula fixed to values more according to usual
chemical conventions.                 miguel
;
_cod_original_formula_sum            'C12 H12 I2 N2 O4'
_cod_original_formula_weight         502.04
_cod_original_formula_moiety         '2(I), 2(C6 H6 N O2)'
_cod_original_formula_units_Z            1
_cod_database_code               7131468
_shelx_shelxl_version_number     2018/3
_chemical_oxdiff_formula         'C1 H1 N1 O1 I1'
_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   0.591
_shelx_estimated_absorpt_t_min   0.508
_reflns_odcompleteness_completeness 99.11
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     27.82
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All O(H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C1(H1), C2(H2), C3(H3), C5(H5)
2.b Idealised tetrahedral OH refined as rotating group:
 O1(H1A)
;
_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 1.806
_oxdiff_exptl_absorpt_empirical_full_min 0.540
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -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
I1 I 0.53493(4) 1.29744(4) -0.23922(3) 0.04496(13) Uani 1 1 d . . . . .
C1 C 1.3061(8) 1.2474(8) 0.3867(7) 0.0535(12) Uani 1 1 d . . . . .
H1 H 1.405434 1.252053 0.439863 0.064 Uiso 1 1 calc R U . . .
O1 O 0.8941(6) 1.2687(7) -0.0280(5) 0.0615(10) Uani 1 1 d . . . . .
H1A H 0.804662 1.264945 -0.072533 0.092 Uiso 1 1 calc R U . . .
N1 N 1.3284(6) 1.2492(7) 0.2217(6) 0.0481(9) Uani 1 1 d . . . . .
H1B H 1.433(9) 1.252(9) 0.172(8) 0.054(16) Uiso 1 1 d . . . . .
C2 C 1.1367(8) 1.2385(9) 0.4798(7) 0.0547(12) Uani 1 1 d . . . . .
H2 H 1.119805 1.237840 0.596334 0.066 Uiso 1 1 calc R U . . .
O2 O 0.7381(5) 1.1647(6) 0.2055(5) 0.0539(8) Uani 1 1 d . . . . .
C3 C 0.9906(7) 1.2305(8) 0.3992(6) 0.0469(10) Uani 1 1 d . . . . .
H3 H 0.874814 1.223898 0.460781 0.056 Uiso 1 1 calc R U . . .
C4 C 1.0194(6) 1.2325(6) 0.2257(5) 0.0369(8) Uani 1 1 d . . . . .
C5 C 1.1920(6) 1.2434(7) 0.1373(6) 0.0427(9) Uani 1 1 d . . . . .
H5 H 1.212932 1.246554 0.020558 0.051 Uiso 1 1 calc R U . . .
C6 C 0.8678(6) 1.2176(7) 0.1341(6) 0.0409(9) Uani 1 1 d . . . . .
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'
I I -0.4742 1.8119 '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
N1 C1 H1 120.0 . . ?
N1 C1 C2 119.9(4) . . ?
C2 C1 H1 120.0 . . ?
C6 O1 H1A 109.5 . . ?
C1 N1 H1B 116(5) . . ?
C1 N1 C5 123.2(4) . . ?
C5 N1 H1B 120(5) . . ?
C1 C2 H2 120.3 . . ?
C1 C2 C3 119.5(5) . . ?
C3 C2 H2 120.3 . . ?
C2 C3 H3 120.5 . . ?
C2 C3 C4 119.0(4) . . ?
C4 C3 H3 120.5 . . ?
C3 C4 C6 120.7(4) . . ?
C5 C4 C3 119.4(4) . . ?
C5 C4 C6 119.9(4) . . ?
N1 C5 C4 119.1(4) . . ?
N1 C5 H5 120.5 . . ?
C4 C5 H5 120.5 . . ?
O1 C6 C4 112.5(4) . . ?
O2 C6 O1 125.6(4) . . ?
O2 C6 C4 121.9(4) . . ?
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
C1 H1 0.9300 . ?
C1 N1 1.316(7) . ?
C1 C2 1.368(8) . ?
O1 H1A 0.8200 . ?
O1 C6 1.316(6) . ?
N1 H1B 0.82(6) . ?
N1 C5 1.334(6) . ?
C2 H2 0.9300 . ?
C2 C3 1.382(7) . ?
O2 C6 1.205(5) . ?
C3 H3 0.9300 . ?
C3 C4 1.383(7) . ?
C4 C5 1.378(6) . ?
C4 C6 1.497(6) . ?
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
C1 N1 C5 C4 -0.8(8) . . . . ?
C1 C2 C3 C4 -0.3(8) . . . . ?
N1 C1 C2 C3 0.3(9) . . . . ?
C2 C1 N1 C5 0.2(8) . . . . ?
C2 C3 C4 C5 -0.3(7) . . . . ?
C2 C3 C4 C6 178.0(5) . . . . ?
C3 C4 C5 N1 0.8(7) . . . . ?
C3 C4 C6 O1 164.6(5) . . . . ?
C3 C4 C6 O2 -15.1(7) . . . . ?
C5 C4 C6 O1 -17.0(6) . . . . ?
C5 C4 C6 O2 163.2(5) . . . . ?
C6 C4 C5 N1 -177.5(4) . . . . ?
