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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/7/21/58/7215853.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_7215853
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         'C12 H18 N O4'
_chemical_formula_sum            'C12 H18 N O4'
_chemical_formula_weight         240.27
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2yn'
_symmetry_space_group_name_H-M   'P 1 21/n 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 93.872(3)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   5.4960(9)
_cell_length_b                   12.831(2)
_cell_length_c                   17.881(3)
_cell_measurement_temperature    293(2)
_cell_volume                     1258.1(4)
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 0.966
_diffrn_measured_fraction_theta_max 0.966
_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  0.0572
_diffrn_reflns_av_sigmaI/netI    0.0655
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            7893
_diffrn_reflns_theta_full        28.32
_diffrn_reflns_theta_max         28.32
_diffrn_reflns_theta_min         1.96
_exptl_absorpt_coefficient_mu    0.095
_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    1.269
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             516
_exptl_crystal_size_max          0.25
_exptl_crystal_size_mid          0.18
_exptl_crystal_size_min          0.15
_refine_diff_density_max         0.377
_refine_diff_density_min         -0.327
_refine_diff_density_rms         0.074
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.083
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     154
_refine_ls_number_reflns         3037
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.083
_refine_ls_R_factor_all          0.0991
_refine_ls_R_factor_gt           0.0791
_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)+(0.1407P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2230
_refine_ls_wR_factor_ref         0.2435
_reflns_number_gt                2063
_reflns_number_total             3037
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            c4ce00749b2.cif
_cod_data_source_block           compound1
_cod_depositor_comments
'Adding full bibliography for 7215853--7215860.cif.'
_cod_original_cell_volume        1258.0(3)
_cod_original_sg_symbol_H-M      P21/n
_cod_database_code               7215853
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
N1 N 0.1715(3) 0.93495(12) 0.47395(9) 0.0466(4) Uani 1 1 d .
O1 O 0.5318(3) 0.80557(15) 0.43543(10) 0.0776(6) Uani 1 1 d .
H1 H 0.4256 0.8502 0.4374 0.080 Uiso 1 1 calc .
C10 C 0.6293(4) 0.57734(15) 0.41795(10) 0.0461(5) Uani 1 1 d .
H10A H 0.6447 0.6020 0.4693 0.055 Uiso 1 1 calc R
H10B H 0.4628 0.5538 0.4074 0.055 Uiso 1 1 calc R
C11 C 0.6802(3) 0.66739(14) 0.36559(10) 0.0416(4) Uani 1 1 d .
H11A H 0.8422 0.6956 0.3801 0.050 Uiso 1 1 calc R
C7 C 0.4944(4) 0.75181(15) 0.37403(12) 0.0495(5) Uani 1 1 d .
C12 C 0.8585(4) 0.53818(19) 0.27829(13) 0.0603(6) Uani 1 1 d .
H12A H 0.8515 0.5140 0.2268 0.072 Uiso 1 1 calc R
H12B H 1.0227 0.5629 0.2912 0.072 Uiso 1 1 calc R
O2 O 0.5454(3) 0.38137(14) 0.23018(10) 0.0735(6) Uani 1 1 d .
H2 H 0.4181 0.3504 0.2184 0.080 Uiso 1 1 calc .
C1 C 0.0252(4) 0.90135(14) 0.52607(11) 0.0462(5) Uani 1 1 d .
C9 C 0.5708(4) 0.39142(15) 0.30387(13) 0.0532(5) Uani 1 1 d .
C8 C 0.6790(4) 0.62827(17) 0.28474(11) 0.0531(6) Uani 1 1 d .
H8A H 0.5161 0.6052 0.2682 0.064 Uiso 1 1 calc R
H8B H 0.7230 0.6849 0.2524 0.064 Uiso 1 1 calc R
O3 O 0.3256(4) 0.76615(18) 0.32981(13) 0.1063(9) Uani 1 1 d .
C6 C 0.8016(4) 0.48606(17) 0.40982(12) 0.0547(5) Uani 1 1 d .
H6A H 0.7529 0.4290 0.4411 0.066 Uiso 1 1 calc R
H6B H 0.9654 0.5068 0.4273 0.066 Uiso 1 1 calc R
C2 C 0.1487(4) 1.03220(15) 0.44781(10) 0.0453(5) Uani 1 1 d .
C5 C 0.8030(4) 0.44852(16) 0.32892(12) 0.0494(5) Uani 1 1 d .
H5A H 0.9372 0.3985 0.3269 0.059 Uiso 1 1 calc R
O4 O 0.4286(4) 0.35642(18) 0.34496(12) 0.0903(7) Uani 1 1 d .
C4 C 0.3172(5) 1.0645(2) 0.38967(14) 0.0686(7) Uani 1 1 d .
H4A H 0.2821 1.1350 0.3746 0.103 Uiso 1 1 calc R
H4B H 0.2948 1.0193 0.3470 0.103 Uiso 1 1 calc R
H4C H 0.4829 1.0598 0.4101 0.103 Uiso 1 1 calc R
C3 C 0.0581(5) 0.79196(16) 0.55365(16) 0.0698(7) Uani 1 1 d .
H3A H -0.0575 0.7777 0.5903 0.105 Uiso 1 1 calc R
H3B H 0.2205 0.7834 0.5761 0.105 Uiso 1 1 calc R
H3C H 0.0323 0.7445 0.5124 0.105 Uiso 1 1 calc R
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
C2 N1 C1 119.76(16) . .
C7 O1 H1 109.5 . .
C6 C10 C11 112.58(17) . .
C6 C10 H10A 109.1 . .
C11 C10 H10A 109.1 . .
C6 C10 H10B 109.1 . .
C11 C10 H10B 109.1 . .
H10A C10 H10B 107.8 . .
C7 C11 C10 109.29(16) . .
C7 C11 C8 111.82(16) . .
C10 C11 C8 110.02(15) . .
C7 C11 H11A 108.5 . .
C10 C11 H11A 108.5 . .
C8 C11 H11A 108.5 . .
O3 C7 O1 123.3(2) . .
O3 C7 C11 123.2(2) . .
O1 C7 C11 113.39(17) . .
C5 C12 C8 111.95(17) . .
C5 C12 H12A 109.2 . .
C8 C12 H12A 109.2 . .
C5 C12 H12B 109.2 . .
C8 C12 H12B 109.2 . .
H12A C12 H12B 107.9 . .
C9 O2 H2 109.5 . .
N1 C1 C2 119.72(17) . 3_576
N1 C1 C3 117.76(19) . .
C2 C1 C3 122.5(2) 3_576 .
O4 C9 O2 123.1(2) . .
O4 C9 C5 125.0(2) . .
O2 C9 C5 111.9(2) . .
C12 C8 C11 110.96(17) . .
C12 C8 H8A 109.4 . .
C11 C8 H8A 109.4 . .
C12 C8 H8B 109.4 . .
C11 C8 H8B 109.4 . .
H8A C8 H8B 108.0 . .
C10 C6 C5 112.18(16) . .
C10 C6 H6A 109.2 . .
C5 C6 H6A 109.2 . .
C10 C6 H6B 109.2 . .
C5 C6 H6B 109.2 . .
H6A C6 H6B 107.9 . .
N1 C2 C1 120.52(18) . 3_576
N1 C2 C4 116.99(19) . .
C1 C2 C4 122.49(19) 3_576 .
C12 C5 C9 113.10(18) . .
C12 C5 C6 110.04(16) . .
C9 C5 C6 112.05(19) . .
C12 C5 H5A 107.1 . .
C9 C5 H5A 107.1 . .
C6 C5 H5A 107.1 . .
C2 C4 H4A 109.5 . .
C2 C4 H4B 109.5 . .
H4A C4 H4B 109.5 . .
C2 C4 H4C 109.5 . .
H4A C4 H4C 109.5 . .
H4B C4 H4C 109.5 . .
C1 C3 H3A 109.5 . .
C1 C3 H3B 109.5 . .
H3A C3 H3B 109.5 . .
C1 C3 H3C 109.5 . .
H3A C3 H3C 109.5 . .
H3B C3 H3C 109.5 . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
N1 C2 1.335(3) .
N1 C1 1.343(3) .
O1 C7 1.301(3) .
O1 H1 0.8200 .
C10 C6 1.519(3) .
C10 C11 1.525(3) .
C10 H10A 0.9700 .
C10 H10B 0.9700 .
C11 C7 1.503(3) .
C11 C8 1.530(3) .
C11 H11A 0.9800 .
C7 O3 1.192(3) .
C12 C5 1.508(3) .
C12 C8 1.529(3) .
C12 H12A 0.9700 .
C12 H12B 0.9700 .
O2 C9 1.322(3) .
O2 H2 0.8200 .
C1 C2 1.385(3) 3_576
C1 C3 1.495(3) .
C9 O4 1.196(3) .
C9 C5 1.513(3) .
C8 H8A 0.9700 .
C8 H8B 0.9700 .
C6 C5 1.525(3) .
C6 H6A 0.9700 .
C6 H6B 0.9700 .
C2 C1 1.385(3) 3_576
C2 C4 1.497(3) .
C5 H5A 0.9800 .
C4 H4A 0.9600 .
C4 H4B 0.9600 .
C4 H4C 0.9600 .
C3 H3A 0.9600 .
C3 H3B 0.9600 .
C3 H3C 0.9600 .
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 PubChem 139198530
