#------------------------------------------------------------------------------
#$Date: 2025-10-28 23:58:54 +0100 (Tue 28 de Oct de 2025) $
#$Revision: 303078 $
#$URL: svn://www.crystallography.net/cod/cif/7/13/51/7135122.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_7135122
loop_
_publ_author_name
'Scheepers, Matthew C.'
'Haynes, Delia A.'
_publ_section_title
;
 Design and synthesis of ternary multi-component crystals by sublimation.
;
_journal_name_full               'Chemical communications (Cambridge, England)'
_journal_paper_doi               10.1039/d5cc04584c
_journal_year                    2025
_chemical_formula_moiety         'C6 H6 N2 O'
_chemical_formula_sum            'C6 H6 N2 O'
_chemical_formula_weight         122.13
_chemical_name_common            pyridine-4-carboxamide
_chemical_name_systematic        Isonicotinamide
_space_group_IT_number           14
_space_group_name_Hall           '-P 2ybc'
_space_group_name_H-M_alt        'P 1 21/c 1'
_symmetry_cell_setting           monoclinic
_symmetry_Int_Tables_number      14
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 1 21/c 1'
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     dual
_audit_conform_dict_location     ftp://ftp.iucr.org/pub/cif_core.dic
_audit_conform_dict_name         cif_core.dic
_audit_conform_dict_version      2.4.5
_audit_creation_date             2025-09-29T09:18:05-00:00
_audit_creation_method           'WinGX routine CIF_UPDATE'
_audit_update_record
;
2025-10-05 deposited with the CCDC.	2025-10-10 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 105.312(13)
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   15.999(13)
_cell_length_b                   8.007(6)
_cell_length_c                   9.943(8)
_cell_measurement_reflns_used    2694
_cell_measurement_temperature    298(2)
_cell_measurement_theta_max      21.61
_cell_measurement_theta_min      2.64
_cell_measurement_wavelength     0.71073
_cell_volume                     1228.5(17)
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL-2016/6 (Sheldrick, 2016)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_diffrn_ambient_temperature      298(2)
_diffrn_measured_fraction_theta_full 1
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0882
_diffrn_reflns_av_unetI/netI     0.0382
_diffrn_reflns_Laue_measured_fraction_full 1
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_limit_h_max       20
_diffrn_reflns_limit_h_min       -20
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            32473
_diffrn_reflns_point_group_measured_fraction_full 1
_diffrn_reflns_point_group_measured_fraction_max 0.996
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.567
_diffrn_reflns_theta_min         1.32
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.094
_exptl_absorpt_correction_T_max  0.745
_exptl_absorpt_correction_T_min  0.645
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
 SADABS 2016/2: Krause, L., Herbst-Irmer, R., Sheldrick G.M. & Stalke D.,
 J. Appl. Cryst. 48 (2015) 3-10
;
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.321
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             512
_exptl_crystal_recrystallization_method
'Re-crystallisation from solvent: Tetrahydrofuran'
_exptl_crystal_size_max          0.306
_exptl_crystal_size_mid          0.141
_exptl_crystal_size_min          0.052
_refine_diff_density_max         0.233
_refine_diff_density_min         -0.197
_refine_diff_density_rms         0.057
_refine_ls_extinction_coef       0.006(2)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2016/6 (Sheldrick 2016)'
_refine_ls_goodness_of_fit_ref   1.224
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_constraints    0
_refine_ls_number_parameters     180
_refine_ls_number_reflns         2554
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.224
_refine_ls_R_factor_all          0.1183
_refine_ls_R_factor_gt           0.0736
_refine_ls_shift/su_max          0
_refine_ls_shift/su_mean         0
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0842P)²+1.7280P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2495
_refine_ls_wR_factor_ref         0.2696
_reflns_Friedel_coverage         0
_reflns_number_gt                1486
_reflns_number_total             2554
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d5cc04584c2.cif
_cod_data_source_block           isonicFormII
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               7135122
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'
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
C1 C 0.1199(3) 0.9529(5) 0.4967(4) 0.0416(10) Uani 1 1 d . . . . .
C2 C 0.0797(3) 1.0618(5) 0.3928(4) 0.0534(12) Uani 1 1 d . . . . .
H2 H 0.048931 1.021977 0.306008 0.064 Uiso 1 1 calc R U . . .
C3 C 0.0858(3) 1.2317(6) 0.4194(5) 0.0614(13) Uani 1 1 d . . . . .
H3 H 0.057041 1.303679 0.348965 0.074 Uiso 1 1 calc R U . . .
C5 C 0.1706(3) 1.1902(6) 0.6392(5) 0.0587(13) Uani 1 1 d . . . . .
H5 H 0.202948 1.233582 0.723712 0.07 Uiso 1 1 calc R U . . .
C6 C 0.1668(3) 1.0196(5) 0.6235(4) 0.0519(11) Uani 1 1 d . . . . .
H6 H 0.195051 0.949976 0.696275 0.062 Uiso 1 1 calc R U . . .
N1 N 0.1303(3) 1.2982(5) 0.5394(4) 0.0622(11) Uani 1 1 d . . . . .
N2 N 0.1240(3) 0.6680(5) 0.5782(4) 0.0569(11) Uani 1 1 d . . . . .
H2A H 0.124(3) 0.709(6) 0.662(5) 0.058(13) Uiso 1 1 d . . . . .
H2B H 0.123(3) 0.552(7) 0.560(5) 0.067(14) Uiso 1 1 d . . . . .
O1 O 0.1029(2) 0.7150(4) 0.3492(3) 0.0648(10) Uani 1 1 d . . . . .
C7 C 0.1145(3) 0.7675(5) 0.4696(4) 0.0466(10) Uani 1 1 d . . . . .
C8 C 0.3794(3) 0.4538(5) 0.3957(4) 0.0442(10) Uani 1 1 d . . . . .
C9 C 0.4216(3) 0.5616(6) 0.3277(4) 0.0565(12) Uani 1 1 d . . . . .
H9 H 0.452641 0.520827 0.267702 0.068 Uiso 1 1 calc R U . . .
C10 C 0.4172(4) 0.7303(6) 0.3500(5) 0.0650(14) Uani 1 1 d . . . . .
H10 H 0.44668 0.801551 0.3045 0.078 Uiso 1 1 calc R U . . .
C12 C 0.3324(3) 0.6923(6) 0.4963(5) 0.0586(13) Uani 1 1 d . . . . .
H12 H 0.300774 0.736664 0.55399 0.07 Uiso 1 1 calc R U . . .
C13 C 0.3337(3) 0.5209(5) 0.4827(4) 0.0508(11) Uani 1 1 d . . . . .
H13 H 0.30451 0.452381 0.530785 0.061 Uiso 1 1 calc R U . . .
C14 C 0.3830(3) 0.2695(5) 0.3711(4) 0.0487(11) Uani 1 1 d . . . . .
N3 N 0.3731(3) 0.7979(5) 0.4332(4) 0.0653(12) Uani 1 1 d . . . . .
N4 N 0.3707(3) 0.1683(5) 0.4693(4) 0.0627(12) Uani 1 1 d . . . . .
O2 O 0.3955(3) 0.2167(4) 0.2606(3) 0.0688(11) Uani 1 1 d . . . . .
H4A H 0.371(3) 0.042(7) 0.457(5) 0.076(15) Uiso 1 1 d . . . . .
H4B H 0.371(3) 0.210(6) 0.553(5) 0.066(15) Uiso 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 0 '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 0.006 '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
C2 C1 C6 118.1(4) . . ?
C2 C1 C7 119.8(4) . . ?
C6 C1 C7 122.1(4) . . ?
C1 C2 C3 119.0(4) . . ?
C1 C2 H2 120.5 . . ?
C3 C2 H2 120.5 . . ?
N1 C3 C2 124.0(4) . . ?
N1 C3 H3 118 . . ?
C2 C3 H3 118 . . ?
N1 C5 C6 123.8(4) . . ?
N1 C5 H5 118.1 . . ?
C6 C5 H5 118.1 . . ?
C5 C6 C1 118.7(4) . . ?
C5 C6 H6 120.6 . . ?
C1 C6 H6 120.6 . . ?
C3 N1 C5 116.3(4) . . ?
C7 N2 H2A 121(3) . . ?
C7 N2 H2B 117(3) . . ?
H2A N2 H2B 122(4) . . ?
O1 C7 N2 122.9(4) . . ?
O1 C7 C1 119.7(4) . . ?
N2 C7 C1 117.4(3) . . ?
C9 C8 C13 118.2(4) . . ?
C9 C8 C14 119.5(4) . . ?
C13 C8 C14 122.3(4) . . ?
C10 C9 C8 119.0(4) . . ?
C10 C9 H9 120.5 . . ?
C8 C9 H9 120.5 . . ?
N3 C10 C9 123.8(4) . . ?
N3 C10 H10 118.1 . . ?
C9 C10 H10 118.1 . . ?
N3 C12 C13 124.6(4) . . ?
N3 C12 H12 117.7 . . ?
C13 C12 H12 117.7 . . ?
C8 C13 C12 118.2(4) . . ?
C8 C13 H13 120.9 . . ?
C12 C13 H13 120.9 . . ?
O2 C14 N4 122.3(4) . . ?
O2 C14 C8 120.1(4) . . ?
N4 C14 C8 117.6(4) . . ?
C12 N3 C10 116.2(4) . . ?
C14 N4 H4A 121(3) . . ?
C14 N4 H4B 119(3) . . ?
H4A N4 H4B 119(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 C2 1.375(6) . ?
C1 C6 1.392(6) . ?
C1 C7 1.507(6) . ?
C2 C3 1.384(7) . ?
C2 H2 0.93 . ?
C3 N1 1.328(6) . ?
C3 H3 0.93 . ?
C5 N1 1.345(6) . ?
C5 C6 1.375(6) . ?
C5 H5 0.93 . ?
C6 H6 0.93 . ?
N2 C7 1.318(5) . ?
N2 H2A 0.89(5) . ?
N2 H2B 0.95(5) . ?
O1 C7 1.236(5) . ?
C8 C9 1.379(6) . ?
C8 C13 1.381(6) . ?
C8 C14 1.499(6) . ?
C9 C10 1.373(7) . ?
C9 H9 0.93 . ?
C10 N3 1.336(6) . ?
C10 H10 0.93 . ?
C12 N3 1.323(6) . ?
C12 C13 1.380(6) . ?
C12 H12 0.93 . ?
C13 H13 0.93 . ?
C14 O2 1.242(5) . ?
C14 N4 1.323(5) . ?
N4 H4A 1.02(6) . ?
N4 H4B 0.90(5) . ?
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
C6 C1 C2 C3 -1.5(7) . . . . ?
C7 C1 C2 C3 -179.6(4) . . . . ?
C1 C2 C3 N1 1.7(8) . . . . ?
N1 C5 C6 C1 1.1(8) . . . . ?
C2 C1 C6 C5 0.2(7) . . . . ?
C7 C1 C6 C5 178.3(4) . . . . ?
C2 C3 N1 C5 -0.4(7) . . . . ?
C6 C5 N1 C3 -1.0(8) . . . . ?
C2 C1 C7 O1 25.7(6) . . . . ?
C6 C1 C7 O1 -152.3(4) . . . . ?
C2 C1 C7 N2 -155.3(4) . . . . ?
C6 C1 C7 N2 26.7(6) . . . . ?
C13 C8 C9 C10 0.5(7) . . . . ?
C14 C8 C9 C10 179.4(4) . . . . ?
C8 C9 C10 N3 -0.9(8) . . . . ?
C9 C8 C13 C12 0.3(7) . . . . ?
C14 C8 C13 C12 -178.5(4) . . . . ?
N3 C12 C13 C8 -1.0(8) . . . . ?
C9 C8 C14 O2 -25.2(7) . . . . ?
C13 C8 C14 O2 153.6(4) . . . . ?
C9 C8 C14 N4 156.0(4) . . . . ?
C13 C8 C14 N4 -25.2(7) . . . . ?
C13 C12 N3 C10 0.7(8) . . . . ?
C9 C10 N3 C12 0.3(8) . . . . ?
