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#$Date: 2025-08-22 00:26:11 +0300 (Fri, 22 Aug 2025) $
#$Revision: 301853 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/10/19/7101970.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_7101970
loop_
_publ_author_name
'Sreekanth, B. R.'
'Vishweshwar, Peddy'
'Vyas, K.'
_publ_section_title
;
 Supramolecular synthon polymorphism in 2 : 1 co-crystal of
 4-hydroxybenzoic acid and 2,3,5,6-tetramethylpyrazine
;
_journal_coden_ASTM              CHCOFS
_journal_issue                   23
_journal_name_full
;
 Chemical Communications (Cambridge, United Kingdom)
;
_journal_page_first              2375
_journal_page_last               2377
_journal_paper_doi               10.1039/b700082k
_journal_year                    2007
_chemical_formula_moiety         'C8 H12 N2, 2(C7 H6 O3)'
_chemical_formula_sum            'C22 H24 N2 O6'
_chemical_formula_weight         412.44
_space_group_IT_number           14
_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'
_cell_angle_alpha                90
_cell_angle_beta                 109.904(4)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   10.5495(11)
_cell_length_b                   10.3154(9)
_cell_length_c                   10.2205(11)
_cell_measurement_reflns_used    3714
_cell_measurement_temperature    298
_cell_measurement_theta_max      27.5
_cell_measurement_theta_min      2.1
_cell_volume                     1045.8(2)
_computing_cell_refinement       CrystalClear
_computing_data_collection       CrystalClear
_computing_data_reduction        CrystalStructure
_computing_molecular_graphics    'X-Seed 2.0'
_computing_publication_material  'CrystalStructure 3.6.0'
_computing_structure_refinement  CRYSTALS
_computing_structure_solution    SIR92
_diffrn_detector_area_resol_mean 7.31
_diffrn_measured_fraction_theta_full 0.9835
_diffrn_measured_fraction_theta_max 0.9835
_diffrn_measurement_device_type  'Rigaku Mercury'
_diffrn_measurement_method       ω
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.7107
_diffrn_reflns_av_R_equivalents  0.041
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            12161
_diffrn_reflns_theta_full        27.49
_diffrn_reflns_theta_max         27.49
_exptl_absorpt_coefficient_mu    0.096
_exptl_absorpt_correction_T_max  0.986
_exptl_absorpt_correction_T_min  0.953
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'Jacobson, R. (1998) Private communication'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.310
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             436.00
_exptl_crystal_size_max          0.50
_exptl_crystal_size_mid          0.42
_exptl_crystal_size_min          0.15
_refine_diff_density_max         0.31
_refine_diff_density_min         -0.32
_refine_ls_extinction_coef       72.4(16)
_refine_ls_extinction_method
'Larson (1970) Crystallographic Computing eq. 22'
_refine_ls_goodness_of_fit_ref   1.070
_refine_ls_hydrogen_treatment    mixed
_refine_ls_number_parameters     155
_refine_ls_number_reflns         2371
_refine_ls_R_factor_gt           0.0500
_refine_ls_shift/su_max          0.0000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
;
Chebychev polynomial with 3 parameters (Carruthers & Watkin, 1979)
2621.9300 3565.3300 955.7050
;
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_ref         0.0740
_reflns_number_gt                1382
_reflns_number_total             2371
_reflns_threshold_expression     F²>2.0σ(F²)
_cod_data_source_file            b700082k.txt
_cod_data_source_block           4HBA_TMP_form_2
_cod_original_formula_sum        'C22 H24 N2 O6 '
_cod_database_code               7101970
loop_
_symmetry_equiv_pos_site_id
_symmetry_equiv_pos_as_xyz
1 +X,+Y,+Z
2 -X,1/2+Y,1/2-Z
3 -X,-Y,-Z
4 +X,1/2-Y,1/2+Z
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_thermal_displace_type
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_occupancy
_atom_site_U_iso_or_equiv
_atom_site_calc_flag
_atom_site_refinement_flags
N1 N Uani 0.4586(2) 0.1084(2) 0.4201(2) 1.000 0.0450(5) . .
C8 C Uani 0.4152(2) -0.0083(2) 0.3674(2) 1.000 0.0445(6) . .
C9 C Uani 0.4568(2) -0.1194(2) 0.4478(2) 1.000 0.0434(6) . .
C10 C Uani 0.3201(2) -0.0130(2) 0.2197(2) 1.000 0.0703(10) . .
C11 C Uani 0.4137(2) -0.2526(2) 0.3942(2) 1.000 0.0603(8) . .
O1 O Uani 0.35820(10) 0.3258(2) 0.2732(2) 1.000 0.0574(5) . .
O2 O Uani 0.24745(13) 0.33630(10) 0.42240(10) 1.000 0.0527(5) . .
O3 O Uani -0.0336(2) 0.7861(2) -0.0030(2) 1.000 0.0592(6) . .
C1 C Uani 0.1904(2) 0.4857(2) 0.2347(2) 1.000 0.0393(6) . .
C2 C Uani 0.0998(2) 0.5532(2) 0.2805(2) 1.000 0.0438(6) . .
C3 C Uani 0.0246(2) 0.6539(2) 0.2030(2) 1.000 0.0457(6) . .
C4 C Uani 0.0404(2) 0.6890(2) 0.0785(2) 1.000 0.0445(6) . .
C5 C Uani 0.1329(2) 0.6242(2) 0.0332(2) 1.000 0.0490(7) . .
C6 C Uani 0.2069(2) 0.5234(2) 0.1101(2) 1.000 0.0458(6) . .
C7 C Uani 0.2658(2) 0.3770(2) 0.3174(2) 1.000 0.0416(6) . .
H101 H Uiso 0.36980 -0.02160 0.15820 1.000 0.0790 calc R
H102 H Uiso 0.26170 -0.08540 0.20900 1.000 0.0790 calc R
H103 H Uiso 0.26820 0.06440 0.19860 1.000 0.0790 calc R
H111 H Uiso 0.47640 -0.28680 0.35510 1.000 0.0730 calc R
H112 H Uiso 0.41130 -0.30640 0.46880 1.000 0.0730 calc R
H113 H Uiso 0.32660 -0.24970 0.32510 1.000 0.0730 calc R
H1 H Uiso 0.388(3) 0.238(3) 0.324(3) 1.000 0.128(11) d .
H2 H Uiso 0.08860 0.52920 0.36560 1.000 0.0540 calc R
H3 H Uiso -0.03700 0.69990 0.23530 1.000 0.0570 calc R
H5 H Uiso 0.14610 0.65020 -0.05040 1.000 0.0620 calc R
H6 H Uiso 0.26900 0.47790 0.07800 1.000 0.0580 calc R
H30 H Uiso -0.100(3) 0.812(3) 0.028(3) 1.000 0.105(10) d .
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.003 0.002
;
International Tables for Crystallography
(1992, Vol. C, Tables 4.2.6.8 and 6.1.1.4)
;
H H 0.000 0.000
;
International Tables for Crystallography
(1992, Vol. C, Table 6.1.1.4)
;
N N 0.006 0.003
;
International Tables for Crystallography
(1992, Vol. C, Tables 4.2.6.8 and 6.1.1.4)
;
O O 0.011 0.006
;
International Tables for Crystallography
(1992, 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
C7 O1 H1 108.2(18) . . no
C4 O3 H30 110.7(19) . . no
C8 N1 C9 120.01(19) . 3_656 no
C9 C8 C10 122.37(18) . . no
N1 C8 C10 117.05(18) . . no
N1 C8 C9 120.58(19) . . no
N1 C9 C8 119.41(19) 3_656 . no
N1 C9 C11 117.46(18) 3_656 . no
C8 C9 C11 123.12(18) . . no
C8 C10 H103 110.00 . . no
C8 C10 H101 110.00 . . no
C8 C10 H102 109.00 . . no
H102 C10 H103 109.00 . . no
H101 C10 H102 109.00 . . no
H101 C10 H103 109.00 . . no
C9 C11 H111 109.00 . . no
H111 C11 H112 109.00 . . no
C9 C11 H112 109.00 . . no
C9 C11 H113 110.00 . . no
H112 C11 H113 109.00 . . no
H111 C11 H113 110.00 . . no
C2 C1 C7 119.40(18) . . no
C6 C1 C7 121.80(19) . . no
C2 C1 C6 118.81(19) . . no
C1 C2 C3 120.76(19) . . no
C2 C3 C4 119.8(2) . . no
O3 C4 C3 122.0(2) . . no
C3 C4 C5 119.93(19) . . no
O3 C4 C5 118.13(19) . . no
C4 C5 C6 120.07(19) . . no
C1 C6 C5 120.6(2) . . no
O2 C7 C1 123.36(19) . . no
O1 C7 O2 121.22(19) . . no
O1 C7 C1 115.41(18) . . no
C1 C2 H2 120.00 . . no
C3 C2 H2 120.00 . . no
C2 C3 H3 120.00 . . no
C4 C3 H3 120.00 . . no
C4 C5 H5 120.00 . . no
C6 C5 H5 120.00 . . no
C1 C6 H6 119.00 . . no
C5 C6 H6 120.00 . . no
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 C7 1.316(3) . no
O2 C7 1.228(2) . no
O3 C4 1.365(3) . no
O1 H1 1.04(3) . no
O3 H30 0.90(3) . no
N1 C9 1.346(3) 3_656 no
N1 C8 1.335(3) . no
C8 C9 1.391(3) . no
C8 C10 1.502(3) . no
C9 C11 1.492(3) . no
C10 H101 0.9500 . no
C10 H103 0.9500 . no
C10 H102 0.9500 . no
C11 H112 0.9500 . no
C11 H113 0.9500 . no
C11 H111 0.9500 . no
C1 C7 1.465(3) . no
C1 C2 1.386(3) . no
C1 C6 1.398(3) . no
C2 C3 1.381(3) . no
C3 C4 1.387(3) . no
C4 C5 1.386(3) . no
C5 C6 1.375(3) . no
C2 H2 0.9500 . no
C3 H3 0.9500 . no
C5 H5 0.9500 . no
C6 H6 0.9500 . no
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
_geom_hbond_publ_flag
O1 H1 N1 1.04(3) 1.68(3) 2.706(3) 171(2) . yes
O3 H30 O2 0.90(3) 1.81(3) 2.702(3) 170(3) 2_555 yes
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_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C9 N1 C8 C9 -0.1(3) 3_656 . . no
C9 N1 C8 C10 179.5(2) 3_656 . . no
C8 N1 C9 C8 0.1(3) . 3_656 3_656 no
C8 N1 C9 C11 -179.0(2) . 3_656 3_656 no
N1 C8 C9 C11 -179.0(2) . . . no
N1 C8 C9 N1 0.1(3) . . 3_656 no
C10 C8 C9 C11 1.5(3) . . . no
C10 C8 C9 N1 -179.5(2) . . 3_656 no
C6 C1 C2 C3 1.6(3) . . . no
C7 C1 C2 C3 -178.3(2) . . . no
C2 C1 C6 C5 -1.1(3) . . . no
C7 C1 C6 C5 178.7(2) . . . no
C2 C1 C7 O1 -174.15(19) . . . no
C2 C1 C7 O2 4.6(3) . . . no
C6 C1 C7 O1 6.0(3) . . . no
C6 C1 C7 O2 -175.21(19) . . . no
C1 C2 C3 C4 -0.6(3) . . . no
C2 C3 C4 O3 178.7(2) . . . no
C2 C3 C4 C5 -0.9(3) . . . no
O3 C4 C5 C6 -178.2(2) . . . no
C3 C4 C5 C6 1.4(3) . . . no
C4 C5 C6 C1 -0.4(3) . . . no
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 PubChem 67150288
