#------------------------------------------------------------------------------
#$Date: 2022-03-04 03:33:31 +0200 (Fri, 04 Mar 2022) $
#$Revision: 273312 $
#$URL: file:///home/coder/svn-repositories/cod/cif/8/00/05/8000567.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_8000567
loop_
_publ_author_name
'Chen, Yi'
'Xie, Yujun'
'Li, Zhen'
_publ_section_title
;
 Room-Temperature Phosphorescence of Nicotinic Acid and Isonicotinic Acid:
 Efficient Intermolecular Hydrogen-Bond Interaction in Molecular Array.
;
_journal_issue                   7
_journal_name_full               'The journal of physical chemistry letters'
_journal_page_first              1652
_journal_page_last               1659
_journal_paper_doi               10.1021/acs.jpclett.2c00118
_journal_volume                  13
_journal_year                    2022
_chemical_formula_moiety         'C6 H5 N O2'
_chemical_formula_sum            'C6 H5 N O2'
_chemical_formula_weight         123.112
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_symmetry_Int_Tables_number      2
_atom_sites_solution_primary     iterative
_audit_creation_date             2020-10-20
_audit_creation_method
;
Olex2 1.3
(compiled 2020.07.31 svn.rc2a77460 for OlexSys, GUI svn.r6145)
;
_cell_angle_alpha                103.707(10)
_cell_angle_beta                 114.869(11)
_cell_angle_gamma                106.137(10)
_cell_formula_units_Z            2
_cell_length_a                   6.3923(7)
_cell_length_b                   7.2424(9)
_cell_length_c                   7.4683(8)
_cell_measurement_reflns_used    1075
_cell_measurement_temperature    293
_cell_measurement_theta_max      72.9420
_cell_measurement_theta_min      6.9450
_cell_volume                     275.38(8)
_computing_cell_refinement       'CrysAlisPro 1.171.39.46e (Rigaku OD, 2018)'
_computing_data_collection       'CrysAlisPro 1.171.39.46e (Rigaku OD, 2018)'
_computing_data_reduction        'CrysAlisPro 1.171.39.46e (Rigaku OD, 2018)'
_computing_molecular_graphics    'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement  'olex2.refine 1.3 (Bourhis et al., 2015)'
_computing_structure_solution    'olex2.solve 1.3 (Bourhis et al., 2015)'
_diffrn_ambient_temperature      293
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 5.1975
_diffrn_detector_type            AtlasS2
_diffrn_measured_fraction_theta_full 0.9753
_diffrn_measured_fraction_theta_max 0.9754
_diffrn_measurement_details
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
--------------------------------------------------------------------------
  1  ω    -88.00  -4.00   1.00    1.00    --  -41.12 125.00   0.00   84
  2  ω   -108.00 -76.00   1.00    1.00    --  -41.12 -37.00 -90.00   32
  3  ω    -75.00 -17.00   1.00    1.00    --  -41.12 -37.00 -90.00   58
  4  ω     17.00  54.00   1.00    1.00    --   41.12 -57.00 150.00   37
  5  ω    -27.00  15.00   1.00    1.00    --   41.12 -57.00 150.00   42
  6  ω     18.00  53.00   1.00    1.00    --   41.12  37.00 -60.00   35
  7  ω    106.00 178.00   1.00    1.00    --  105.32  61.00   0.00   72
  8  ω     96.00 168.00   1.00    1.00    --  105.32 125.00-180.00   72
  9  ω     48.00 131.00   1.00    1.00    --  105.32 -61.00-120.00   83
 10  ω     52.00 110.00   1.00    1.00    --  105.32-125.00  60.00   58
 11  ω     77.00 168.00   1.00    1.00    --  105.32  77.00-120.00   91
 12  ω     83.00 163.00   1.00    1.00    --  105.32  30.00 -30.00   80
 13  ω     64.00 109.00   1.00    1.00    --  105.32 -94.00-150.00   45
 14  ω    127.00 152.00   1.00    1.00    --  105.32 125.00-150.00   25
 15  ω     23.00  63.00   1.00    1.00    --  105.32 -94.00-150.00   40
 16  ω     35.00 111.00   1.00    1.00    --  105.32-125.00-180.00   76
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at home/near, AtlasS2'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0905934000
_diffrn_orient_matrix_UB_12      -0.1079097000
_diffrn_orient_matrix_UB_13      0.1532040000
_diffrn_orient_matrix_UB_21      -0.1281574000
_diffrn_orient_matrix_UB_22      -0.2102013000
_diffrn_orient_matrix_UB_23      -0.1959943000
_diffrn_orient_matrix_UB_31      0.2485780000
_diffrn_orient_matrix_UB_32      0.0537168000
_diffrn_orient_matrix_UB_33      -0.0035264000
_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  0.0135
_diffrn_reflns_av_unetI/netI     0.0183
_diffrn_reflns_Laue_measured_fraction_full 0.9753
_diffrn_reflns_Laue_measured_fraction_max 0.9754
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -5
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       5
_diffrn_reflns_limit_l_min       -8
_diffrn_reflns_number            1470
_diffrn_reflns_point_group_measured_fraction_full 0.9753
_diffrn_reflns_point_group_measured_fraction_max 0.9754
_diffrn_reflns_theta_full        66.9339
_diffrn_reflns_theta_max         66.93
_diffrn_reflns_theta_min         6.96
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.961
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.35325
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.39.46e (Rigaku Oxford Diffraction, 2018)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_density_diffrn    1.485
_exptl_crystal_description       block
_exptl_crystal_F_000             128.482
_exptl_crystal_size_max          0.4
_exptl_crystal_size_mid          0.3
_exptl_crystal_size_min          0.2
_refine_diff_density_max         0.2680
_refine_diff_density_min         -0.2998
_refine_diff_density_rms         0.0803
_refine_ls_d_res_high            0.8379
_refine_ls_d_res_low             6.3579
_refine_ls_goodness_of_fit_ref   1.0905
_refine_ls_hydrogen_treatment    refall
_refine_ls_matrix_type           full
_refine_ls_number_constraints    0
_refine_ls_number_parameters     102
_refine_ls_number_reflns         950
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.0905
_refine_ls_R_factor_all          0.0597
_refine_ls_R_factor_gt           0.0521
_refine_ls_shift/su_max          0.0000
_refine_ls_shift/su_mean         0.0000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.1531P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1619
_refine_ls_wR_factor_ref         0.1890
_reflns_Friedel_coverage         0.0
_reflns_limit_h_max              6
_reflns_limit_h_min              -7
_reflns_limit_k_max              8
_reflns_limit_k_min              -8
_reflns_limit_l_max              8
_reflns_limit_l_min              0
_reflns_number_gt                859
_reflns_number_total             950
_reflns_threshold_expression     I>=2u(I)
_cod_data_source_file            jz2c00118_si_003.cif
_cod_data_source_block           p-SA
_cod_database_code               8000567
_chemical_oxdiff_formula         C6H5NO2
_reflns_odcompleteness_completeness 97.44
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_olex2_refinement_description
;
;
_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 1.687
_oxdiff_exptl_absorpt_empirical_full_min 0.427
loop_
_space_group_symop_id
_space_group_symop_operation_xyz
1 x,y,z
2 -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_refinement_flags_posn
O001 O 0.6274(3) 0.7818(2) 0.7111(2) 0.0573(6) Uani 1.000000 .
O002 O 0.9448(3) 0.6862(3) 0.7711(2) 0.0624(6) Uani 1.000000 .
N003 N 0.6889(2) 0.7623(2) 0.0695(2) 0.0450(6) Uani 1.000000 .
C004 C 0.5591(3) 0.7934(3) 0.3264(3) 0.0439(6) Uani 1.000000 .
C005 C 0.7487(3) 0.7447(2) 0.4531(2) 0.0380(6) Uani 1.000000 .
C006 C 0.7847(3) 0.7348(2) 0.6628(3) 0.0420(6) Uani 1.000000 .
C007 C 0.9071(3) 0.7040(3) 0.3835(3) 0.0432(5) Uani 1.000000 .
C008 C 0.8694(3) 0.7131(3) 0.1902(3) 0.0452(6) Uani 1.000000 .
C009 C 0.5357(3) 0.8010(3) 0.1363(3) 0.0468(6) Uani 1.000000 .
H009 H 0.412(4) 0.833(3) 0.048(4) 0.067(6) Uiso 1.000000 .
H007 H 1.036(4) 0.679(3) 0.460(4) 0.059(6) Uiso 1.000000 .
H001 H 0.661(5) 0.773(4) 0.858(5) 0.085(8) Uiso 1.000000 .
H008 H 0.973(4) 0.682(4) 0.129(5) 0.071(6) Uiso 1.000000 .
H004 H 0.441(5) 0.823(4) 0.371(5) 0.071(7) Uiso 1.000000 .
loop_
_atom_type_symbol
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_Cromer_Mann_a1
_atom_type_scat_Cromer_Mann_a2
_atom_type_scat_Cromer_Mann_a3
_atom_type_scat_Cromer_Mann_a4
_atom_type_scat_Cromer_Mann_b1
_atom_type_scat_Cromer_Mann_b2
_atom_type_scat_Cromer_Mann_b3
_atom_type_scat_Cromer_Mann_b4
_atom_type_scat_Cromer_Mann_c
_atom_type_scat_source
_atom_type_scat_dispersion_source
H 0.00000 0.00000 0.49300 0.32291 0.14019 0.04081 10.51090 26.12570 3.14236
57.79970 0.0030380000826
'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'
C 0.01920 0.00962 2.31000 1.02000 1.58860 0.86500 20.84390 10.20750 0.56870
51.65120 0.215599998832
'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'
O 0.05239 0.03377 3.04850 2.28680 1.54630 0.86700 13.27710 5.70110 0.32390
32.90890 0.250800013542
'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'
N 0.03256 0.01839 12.21260 3.13220 2.01250 1.16630 0.00570 9.89330 28.99750
0.58260 -11.5290002823
'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'
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
C009 N003 C008 118.68(14) . . ?
C009 C004 C005 118.95(16) . . ?
C006 C005 C004 121.45(16) . . ?
C007 C005 C004 118.75(17) . . ?
C007 C005 C006 119.81(16) . . ?
O002 C006 O001 124.89(16) . . ?
C005 C006 O001 113.27(15) . . ?
C005 C006 O002 121.83(15) . . ?
C008 C007 C005 118.66(17) . . ?
C007 C008 N003 122.65(15) . . ?
C004 C009 N003 122.31(16) . . ?
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
O001 C006 1.301(2) . ?
O002 C006 1.211(2) . ?
N003 C008 1.333(2) . ?
N003 C009 1.336(2) . ?
C004 C005 1.385(3) . ?
C004 C009 1.380(3) . ?
C005 C006 1.507(2) . ?
C005 C007 1.385(2) . ?
C007 C008 1.381(3) . ?
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
O001 C006 C005 C004 -1.83(15) . . . . ?
O001 C006 C005 C007 178.30(17) . . . . ?
O002 C006 C005 C004 177.7(2) . . . . ?
O002 C006 C005 C007 -2.14(18) . . . . ?
N003 C008 C007 C005 0.97(18) . . . . ?
N003 C009 C004 C005 0.24(17) . . . . ?
C004 C005 C007 C008 -0.17(16) . . . . ?
