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#$Date: 2025-08-22 17:55:42 +0300 (Fri, 22 Aug 2025) $
#$Revision: 301864 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/21/58/7215858.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_7215858
loop_
_publ_author_name
'Wang, Lei'
'Xue, Ruiyu'
'Li, Yuanxin'
'Zhao, Yiran'
'Liu, Faqian'
'Huang, Keke'
_publ_section_title
;
 Hydrogen-bonding patterns in a series of multi-component molecular solids
 formed by 2,3,5,6-tetramethylpyrazine with selected carboxylic acids
;
_journal_issue                   30
_journal_name_full               CrystEngComm
_journal_page_first              7074
_journal_paper_doi               10.1039/C4CE00749B
_journal_volume                  16
_journal_year                    2014
_chemical_formula_moiety         'C16 H18 N2 O4'
_chemical_formula_sum            'C16 H18 N2 O4'
_chemical_formula_weight         302.32
_space_group_IT_number           2
_symmetry_cell_setting           triclinic
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                99.769(4)
_cell_angle_beta                 103.689(4)
_cell_angle_gamma                108.465(3)
_cell_formula_units_Z            2
_cell_length_a                   7.5343(14)
_cell_length_b                   8.9454(17)
_cell_length_c                   12.885(3)
_cell_measurement_temperature    293(2)
_cell_volume                     771.6(3)
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 'ACTA 50'
_diffrn_measured_fraction_theta_max 0.921
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0486
_diffrn_reflns_av_sigmaI/netI    0.0793
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            4994
_diffrn_reflns_theta_full        'ACTA 50'
_diffrn_reflns_theta_max         28.36
_diffrn_reflns_theta_min         1.69
_exptl_absorpt_coefficient_mu    0.094
_exptl_absorpt_correction_T_max  0.0001
_exptl_absorpt_correction_T_min  0.0001
_exptl_absorpt_correction_type   empirical
_exptl_absorpt_process_details   SADABS
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.301
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             320
_exptl_crystal_size_max          0.24
_exptl_crystal_size_mid          0.18
_exptl_crystal_size_min          0.16
_refine_diff_density_max         0.347
_refine_diff_density_min         -0.545
_refine_diff_density_rms         0.104
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.053
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     199
_refine_ls_number_reflns         3537
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.053
_refine_ls_R_factor_all          0.0967
_refine_ls_R_factor_gt           0.0873
_refine_ls_shift/su_max          0.004
_refine_ls_shift/su_mean         0.001
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.1743P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2292
_refine_ls_wR_factor_ref         0.2474
_reflns_number_gt                2786
_reflns_number_total             3537
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            c4ce00749b2.cif
_cod_data_source_block           compound6
_cod_depositor_comments
'Adding full bibliography for 7215853--7215860.cif.'
_cod_original_sg_symbol_H-M      P-1
_cod_database_code               7215858
loop_
_symmetry_equiv_pos_as_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_symmetry_multiplicity
_atom_site_calc_flag
O3 O 0.0987(2) 0.65567(17) 0.59750(14) 0.0561(4) Uani 1 1 d
H3 H 0.1806 0.6450 0.5679 0.080 Uiso 1 1 calc
N2 N 0.3622(2) 0.55607(19) 0.52558(13) 0.0430(4) Uani 1 1 d
O1 O 0.2729(2) 0.7765(2) 0.83397(14) 0.0579(4) Uani 1 1 d
C12 C -0.0254(2) 0.8366(2) 0.67791(15) 0.0378(4) Uani 1 1 d
C16 C 0.1199(3) 0.8096(2) 0.62238(15) 0.0418(4) Uani 1 1 d
O4 O 0.2351(2) 0.9173(2) 0.59997(16) 0.0653(5) Uani 1 1 d
C13 C -0.1518(3) 0.9058(2) 0.62750(17) 0.0473(5) Uani 1 1 d
H13 H -0.1381 0.9408 0.5649 0.080 Uiso 1 1 calc
C15 C 0.1058(3) 0.7328(2) 0.83517(15) 0.0420(4) Uani 1 1 d
O2 O 0.0366(2) 0.6328(2) 0.89270(14) 0.0627(5) Uani 1 1 d
H2 H 0.1239 0.6056 0.9251 0.080 Uiso 1 1 calc
C11 C -0.0430(2) 0.7889(2) 0.77351(16) 0.0396(4) Uani 1 1 d
C8 C 0.4240(3) 0.5879(2) 0.44108(15) 0.0427(4) Uani 1 1 d
C14 C -0.2985(3) 0.9224(2) 0.6708(2) 0.0542(6) Uani 1 1 d
H14 H -0.3847 0.9668 0.6361 0.080 Uiso 1 1 calc
C7 C 0.4347(3) 0.4681(2) 0.58551(15) 0.0430(4) Uani 1 1 d
C10 C -0.1900(3) 0.8084(3) 0.81604(19) 0.0513(5) Uani 1 1 d
H10 H -0.2024 0.7768 0.8799 0.080 Uiso 1 1 calc
C9 C -0.3178(3) 0.8742(3) 0.7642(2) 0.0561(6) Uani 1 1 d
H9 H -0.4167 0.8858 0.7927 0.080 Uiso 1 1 calc
C6 C 0.3365(4) 0.6847(4) 0.3762(2) 0.0696(7) Uani 1 1 d
H6A H 0.2437 0.7120 0.4076 0.080 Uiso 1 1 calc
H6B H 0.2706 0.6211 0.3007 0.080 Uiso 1 1 calc
H6C H 0.4390 0.7832 0.3786 0.080 Uiso 1 1 calc
C5 C 0.3570(5) 0.4319(4) 0.6776(2) 0.0726(7) Uani 1 1 d
H5A H 0.2615 0.4808 0.6818 0.080 Uiso 1 1 calc
H5B H 0.4631 0.4756 0.7461 0.080 Uiso 1 1 calc
H5C H 0.2959 0.3157 0.6646 0.080 Uiso 1 1 calc
N1 N 0.3364(2) 0.53950(18) 0.98531(12) 0.0451(4) Uani 1 1 d
C3 C 0.3206(3) 0.3886(2) 0.93924(14) 0.0439(4) Uani 1 1 d
C2 C 0.5134(3) 0.6512(2) 1.04614(15) 0.0458(5) Uani 1 1 d
C4 C 0.1178(3) 0.2690(3) 0.8732(2) 0.0635(6) Uani 1 1 d
H4A H 0.0249 0.3214 0.8744 0.080 Uiso 1 1 calc
H4B H 0.0848 0.1780 0.9048 0.080 Uiso 1 1 calc
H4C H 0.1138 0.2307 0.7981 0.080 Uiso 1 1 calc
C1 C 0.5201(4) 0.8175(3) 1.0968(2) 0.0742(8) Uani 1 1 d
H1A H 0.3895 0.8186 1.0768 0.080 Uiso 1 1 calc
H1B H 0.6028 0.8974 1.0700 0.080 Uiso 1 1 calc
H1C H 0.5721 0.8430 1.1759 0.080 Uiso 1 1 calc
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'
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
C16 O3 H3 109.5 . .
C8 N2 C7 119.50(15) . .
C13 C12 C11 119.74(17) . .
C13 C12 C16 117.41(17) . .
C11 C12 C16 122.78(14) . .
O4 C16 O3 125.13(18) . .
O4 C16 C12 123.04(17) . .
O3 C16 C12 111.76(16) . .
C14 C13 C12 119.8(2) . .
C14 C13 H13 120.1 . .
C12 C13 H13 120.1 . .
O1 C15 O2 123.51(16) . .
O1 C15 C11 123.25(18) . .
O2 C15 C11 113.23(16) . .
C15 O2 H2 109.5 . .
C10 C11 C12 119.37(17) . .
C10 C11 C15 120.39(18) . .
C12 C11 C15 119.99(15) . .
N2 C8 C7 120.62(16) . 2_666
N2 C8 C6 117.28(17) . .
C7 C8 C6 122.10(19) 2_666 .
C9 C14 C13 120.66(18) . .
C9 C14 H14 119.7 . .
C13 C14 H14 119.7 . .
N2 C7 C8 119.88(17) . 2_666
N2 C7 C5 117.53(17) . .
C8 C7 C5 122.58(18) 2_666 .
C9 C10 C11 120.6(2) . .
C9 C10 H10 119.7 . .
C11 C10 H10 119.7 . .
C14 C9 C10 119.79(18) . .
C14 C9 H9 120.1 . .
C10 C9 H9 120.1 . .
C8 C6 H6A 109.5 . .
C8 C6 H6B 109.5 . .
H6A C6 H6B 109.5 . .
C8 C6 H6C 109.5 . .
H6A C6 H6C 109.5 . .
H6B C6 H6C 109.5 . .
C7 C5 H5A 109.5 . .
C7 C5 H5B 109.5 . .
H5A C5 H5B 109.5 . .
C7 C5 H5C 109.5 . .
H5A C5 H5C 109.5 . .
H5B C5 H5C 109.5 . .
C3 N1 C2 119.36(16) . .
N1 C3 C2 120.19(17) . 2_667
N1 C3 C4 116.63(18) . .
C2 C3 C4 123.18(18) 2_667 .
N1 C2 C3 120.45(17) . 2_667
N1 C2 C1 116.56(18) . .
C3 C2 C1 122.99(19) 2_667 .
C3 C4 H4A 109.5 . .
C3 C4 H4B 109.5 . .
H4A C4 H4B 109.5 . .
C3 C4 H4C 109.5 . .
H4A C4 H4C 109.5 . .
H4B C4 H4C 109.5 . .
C2 C1 H1A 109.5 . .
C2 C1 H1B 109.5 . .
H1A C1 H1B 109.5 . .
C2 C1 H1C 109.5 . .
H1A C1 H1C 109.5 . .
H1B C1 H1C 109.5 . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
O3 C16 1.308(2) .
O3 H3 0.8200 .
N2 C8 1.321(2) .
N2 C7 1.339(2) .
O1 C15 1.199(2) .
C12 C13 1.389(2) .
C12 C11 1.392(3) .
C12 C16 1.499(2) .
C16 O4 1.203(2) .
C13 C14 1.387(3) .
C13 H13 0.9300 .
C15 O2 1.317(2) .
C15 C11 1.487(2) .
O2 H2 0.8200 .
C11 C10 1.391(3) .
C8 C7 1.398(3) 2_666
C8 C6 1.494(3) .
C14 C9 1.369(4) .
C14 H14 0.9300 .
C7 C8 1.398(3) 2_666
C7 C5 1.481(3) .
C10 C9 1.381(3) .
C10 H10 0.9300 .
C9 H9 0.9300 .
C6 H6A 0.9600 .
C6 H6B 0.9600 .
C6 H6C 0.9600 .
C5 H5A 0.9600 .
C5 H5B 0.9600 .
C5 H5C 0.9600 .
N1 C3 1.335(2) .
N1 C2 1.337(2) .
C3 C2 1.385(3) 2_667
C3 C4 1.498(3) .
C2 C3 1.385(3) 2_667
C2 C1 1.500(3) .
C4 H4A 0.9600 .
C4 H4B 0.9600 .
C4 H4C 0.9600 .
C1 H1A 0.9600 .
C1 H1B 0.9600 .
C1 H1C 0.9600 .
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 PubChem 139198535
