#------------------------------------------------------------------------------
#$Date: 2016-03-26 22:25:00 +0200 (Sat, 26 Mar 2016) $
#$Revision: 180504 $
#$URL: svn://www.crystallography.net/cod/cif/7/21/73/7217372.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_7217372
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_sum            'C12 H13 N2 O7'
_chemical_formula_weight         297.24
_chemical_name_systematic
; 
 ? 
;
_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                88.282(2)
_cell_angle_beta                 72.1630(10)
_cell_angle_gamma                84.647(2)
_cell_formula_units_Z            2
_cell_length_a                   7.8574(13)
_cell_length_b                   8.3711(11)
_cell_length_c                   11.1437(13)
_cell_measurement_temperature    293(2)
_cell_volume                     694.70(17)
_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 0.917
_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  0.0591
_diffrn_reflns_av_sigmaI/netI    0.0458
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            4452
_diffrn_reflns_theta_full        'ACTA 50'
_diffrn_reflns_theta_max         28.30
_diffrn_reflns_theta_min         2.44
_exptl_absorpt_coefficient_mu    0.119
_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    1.421
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             310
_exptl_crystal_size_max          0.24
_exptl_crystal_size_mid          0.18
_exptl_crystal_size_min          0.15
_refine_diff_density_max         0.347
_refine_diff_density_min         -0.331
_refine_diff_density_rms         0.075
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.071
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     198
_refine_ls_number_reflns         3172
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.071
_refine_ls_R_factor_all          0.0692
_refine_ls_R_factor_gt           0.0612
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.1007P)²+0.2194P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1773
_refine_ls_wR_factor_ref         0.1872
_reflns_number_gt                2641
_reflns_number_total             3172
_reflns_threshold_expression     >2sigma(I)
_cod_duplicate_entry             7215857
_cod_data_source_file            c4ce00749b2.cif
_cod_data_source_block           compound5
_cod_original_sg_symbol_H-M      P-1
_cod_database_code               7217372
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
_atom_site_refinement_flags
N1 N 0.31881(19) 0.49474(16) 0.04658(14) 0.0383(3) Uani 1 1 d .
O4 O -0.02993(16) 0.47263(16) 0.13932(12) 0.0450(3) Uani 1 1 d .
H4 H 0.0774 0.4860 0.1162 0.080 Uiso 1 1 calc .
O2 O -0.08052(19) 0.26019(18) 0.36687(16) 0.0597(4) Uani 1 1 d .
C12 C -0.3039(2) 0.5144(2) 0.29496(15) 0.0356(4) Uani 1 1 d .
O1 O -0.03205(18) 0.60958(18) 0.30834(15) 0.0551(4) Uani 1 1 d .
C7 C -0.3639(2) 0.3701(2) 0.35146(16) 0.0378(4) Uani 1 1 d .
C6 C -0.1053(2) 0.5380(2) 0.24871(17) 0.0378(4) Uani 1 1 d .
C4 C 0.3862(2) 0.63143(19) -0.00308(17) 0.0382(4) Uani 1 1 d .
C11 C -0.4349(2) 0.6320(2) 0.28115(17) 0.0404(4) Uani 1 1 d .
C3 C 0.4283(2) 0.36323(19) 0.05086(16) 0.0380(4) Uani 1 1 d .
N2 N -0.3825(2) 0.7861(2) 0.22164(18) 0.0545(4) Uani 1 1 d .
C10 C -0.6163(2) 0.6096(3) 0.31970(18) 0.0473(4) Uani 1 1 d .
H10A H -0.6997 0.6911 0.3094 0.057 Uiso 1 1 calc R
C9 C -0.6715(3) 0.4661(3) 0.37325(19) 0.0502(5) Uani 1 1 d .
H9A H -0.7927 0.4490 0.3986 0.060 Uiso 1 1 calc R
C8 C -0.5459(3) 0.3471(2) 0.38925(18) 0.0460(4) Uani 1 1 d .
H8A H -0.5836 0.2501 0.4259 0.055 Uiso 1 1 calc R
O1W O -0.1019(3) 0.8724(2) 0.4620(2) 0.0784(6) Uani 1 1 d .
O3 O -0.3087(2) 0.10907(19) 0.4185(2) 0.0825(7) Uani 1 1 d .
H3 H -0.2334 0.0413 0.4308 0.080 Uiso 1 1 calc .
C5 C -0.2337(2) 0.2412(2) 0.37765(17) 0.0420(4) Uani 1 1 d .
C2 C 0.3416(3) 0.2154(2) 0.1082(2) 0.0535(5) Uani 1 1 d .
H2A H 0.4327 0.1300 0.1068 0.080 Uiso 1 1 calc R
H2B H 0.2666 0.1843 0.0608 0.080 Uiso 1 1 calc R
H2C H 0.2700 0.2372 0.1938 0.080 Uiso 1 1 calc R
O6 O -0.5004(3) 0.8901(2) 0.2237(3) 0.1068(9) Uani 1 1 d .
C1 C 0.2548(3) 0.7736(2) -0.0029(2) 0.0548(5) Uani 1 1 d .
H1A H 0.3187 0.8636 -0.0410 0.082 Uiso 1 1 calc R
H1B H 0.1848 0.7996 0.0823 0.082 Uiso 1 1 calc R
H1C H 0.1768 0.7485 -0.0499 0.082 Uiso 1 1 calc R
O5 O -0.2272(3) 0.8018(2) 0.1674(2) 0.0888(7) Uani 1 1 d .
H1WB H -0.057(5) 0.854(5) 0.520(4) 0.106(12) Uiso 1 1 d .
H1WA H -0.082(5) 0.795(5) 0.419(4) 0.099(12) 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 0.0000 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
C4 N1 C3 120.50(15) . .
C6 O4 H4 109.5 . .
C11 C12 C7 116.77(15) . .
C11 C12 C6 122.40(16) . .
C7 C12 C6 120.81(14) . .
C8 C7 C12 120.45(16) . .
C8 C7 C5 119.15(16) . .
C12 C7 C5 120.34(15) . .
O1 C6 O4 126.18(16) . .
O1 C6 C12 122.91(16) . .
O4 C6 C12 110.91(14) . .
N1 C4 C3 119.62(15) . 2_665
N1 C4 C1 117.21(16) . .
C3 C4 C1 123.17(16) 2_665 .
C10 C11 C12 122.82(17) . .
C10 C11 N2 117.09(16) . .
C12 C11 N2 120.07(16) . .
N1 C3 C4 119.88(15) . 2_665
N1 C3 C2 116.97(16) . .
C4 C3 C2 123.14(16) 2_665 .
O5 N2 O6 122.5(2) . .
O5 N2 C11 119.67(16) . .
O6 N2 C11 117.75(19) . .
C9 C10 C11 119.27(17) . .
C9 C10 H10A 120.4 . .
C11 C10 H10A 120.4 . .
C10 C9 C8 119.58(17) . .
C10 C9 H9A 120.2 . .
C8 C9 H9A 120.2 . .
C9 C8 C7 121.09(18) . .
C9 C8 H8A 119.5 . .
C7 C8 H8A 119.5 . .
H1WB O1W H1WA 108(4) . .
C5 O3 H3 109.5 . .
O2 C5 O3 124.10(17) . .
O2 C5 C7 123.56(16) . .
O3 C5 C7 112.28(16) . .
C3 C2 H2A 109.5 . .
C3 C2 H2B 109.5 . .
H2A C2 H2B 109.5 . .
C3 C2 H2C 109.5 . .
H2A C2 H2C 109.5 . .
H2B C2 H2C 109.5 . .
C4 C1 H1A 109.5 . .
C4 C1 H1B 109.5 . .
H1A C1 H1B 109.5 . .
C4 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
N1 C4 1.338(2) .
N1 C3 1.342(2) .
O4 C6 1.294(2) .
O4 H4 0.8200 .
O2 C5 1.198(2) .
C12 C11 1.396(2) .
C12 C7 1.399(2) .
C12 C6 1.516(2) .
O1 C6 1.206(2) .
C7 C8 1.391(3) .
C7 C5 1.501(2) .
C4 C3 1.395(3) 2_665
C4 C1 1.501(2) .
C11 C10 1.386(3) .
C11 N2 1.468(3) .
C3 C4 1.395(3) 2_665
C3 C2 1.499(2) .
N2 O5 1.202(3) .
N2 O6 1.206(2) .
C10 C9 1.373(3) .
C10 H10A 0.9300 .
C9 C8 1.383(3) .
C9 H9A 0.9300 .
C8 H8A 0.9300 .
O1W H1WB 0.83(4) .
O1W H1WA 0.79(4) .
O3 C5 1.305(2) .
O3 H3 0.8200 .
C2 H2A 0.9600 .
C2 H2B 0.9600 .
C2 H2C 0.9600 .
C1 H1A 0.9600 .
C1 H1B 0.9600 .
C1 H1C 0.9600 .
