#------------------------------------------------------------------------------
#$Date: 2016-03-26 22:25:00 +0200 (Sat, 26 Mar 2016) $
#$Revision: 180504 $
#$URL: svn://www.crystallography.net/cod/cif/7/21/73/7217374.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_7217374
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 H12 N O4'
_chemical_formula_sum            'C12 H12 N O4'
_chemical_formula_weight         234.23
_chemical_name_systematic
; 
 ? 
;
_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                 95.937(9)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   7.4101(6)
_cell_length_b                   10.2133(9)
_cell_length_c                   15.0232(16)
_cell_measurement_temperature    293(2)
_cell_volume                     1130.88(18)
_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 0.829
_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  0.0126
_diffrn_reflns_av_sigmaI/netI    0.0209
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            3956
_diffrn_reflns_theta_full        'ACTA 50'
_diffrn_reflns_theta_max         27.35
_diffrn_reflns_theta_min         3.41
_exptl_absorpt_coefficient_mu    0.104
_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    1.376
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             492
_exptl_crystal_size_max          0.25
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.16
_refine_diff_density_max         0.338
_refine_diff_density_min         -0.282
_refine_diff_density_rms         0.045
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.047
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     154
_refine_ls_number_reflns         2123
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.047
_refine_ls_R_factor_all          0.0641
_refine_ls_R_factor_gt           0.0527
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0927P)²+0.4994P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1532
_refine_ls_wR_factor_ref         0.1611
_reflns_number_gt                1727
_reflns_number_total             2123
_reflns_threshold_expression     >2sigma(I)
_cod_duplicate_entry             7215859
_cod_data_source_file            c4ce00749b2.cif
_cod_data_source_block           compound7
_cod_depositor_comments
;
The following automatic conversions were performed:

'_symmetry_cell_setting' value 'Monoclinic' changed to 'monoclinic'
according to
/usr/data/users/saulius/crontab/automatic-downloads/current/RSC/lib/dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.2 from 2011-04-26.

Automatic conversion script
Id: cif_fix_values 2281 2013-09-26 08:29:07Z andrius 
;
_cod_original_sg_symbol_H-M      P21/n
_cod_database_code               7217374
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
O4 O -0.0111(2) 0.63351(17) 0.93238(10) 0.0490(5) Uani 1 1 d .
H4 H -0.1110 0.5998 0.9346 0.080 Uiso 1 1 calc .
C7 C 0.2097(3) 0.6958(2) 0.83883(12) 0.0326(5) Uani 1 1 d .
O2 O 0.2179(2) 0.94319(18) 1.00535(12) 0.0578(5) Uani 1 1 d .
O3 O -0.0105(2) 0.91448(18) 0.89898(12) 0.0579(5) Uani 1 1 d .
H3 H -0.0632 0.9598 0.9332 0.080 Uiso 1 1 calc .
O1 O -0.0663(2) 0.59049(19) 0.78637(11) 0.0572(5) Uani 1 1 d .
C12 C 0.2697(3) 0.8126(2) 0.88046(13) 0.0344(5) Uani 1 1 d .
C5 C 0.0280(3) 0.63532(19) 0.84882(14) 0.0351(5) Uani 1 1 d .
C11 C 0.4431(3) 0.8590(2) 0.86991(16) 0.0444(6) Uani 1 1 d .
H11A H 0.4837 0.9363 0.8980 0.053 Uiso 1 1 calc R
C6 C 0.1508(3) 0.8938(2) 0.93282(15) 0.0382(5) Uani 1 1 d .
C8 C 0.3240(3) 0.6295(2) 0.78641(14) 0.0396(5) Uani 1 1 d .
H8A H 0.2845 0.5525 0.7576 0.047 Uiso 1 1 calc R
C9 C 0.4967(3) 0.6769(3) 0.77658(14) 0.0465(6) Uani 1 1 d .
H9A H 0.5725 0.6312 0.7419 0.056 Uiso 1 1 calc R
C10 C 0.5550(3) 0.7910(3) 0.81796(16) 0.0484(6) Uani 1 1 d .
H10A H 0.6704 0.8229 0.8111 0.058 Uiso 1 1 calc R
N1 N 0.1647(2) 0.96304(16) 0.47312(10) 0.0336(4) Uani 1 1 d .
C4 C 0.0871(3) 0.8928(2) 0.53430(13) 0.0341(5) Uani 1 1 d .
C3 C 0.0805(3) 1.07042(19) 0.43865(13) 0.0340(5) Uani 1 1 d .
C2 C 0.1886(4) 0.7749(3) 0.57221(18) 0.0596(7) Uani 1 1 d .
H2A H 0.1200 0.7328 0.6149 0.089 Uiso 1 1 calc R
H2B H 0.3043 0.8016 0.6012 0.089 Uiso 1 1 calc R
H2C H 0.2066 0.7148 0.5248 0.089 Uiso 1 1 calc R
C1 C 0.1724(4) 1.1452(2) 0.37041(18) 0.0550(7) Uani 1 1 d .
H1A H 0.0995 1.2195 0.3507 0.083 Uiso 1 1 calc R
H1B H 0.1876 1.0895 0.3203 0.083 Uiso 1 1 calc R
H1C H 0.2890 1.1747 0.3966 0.083 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
C5 O4 H4 109.5 . .
C8 C7 C12 119.03(19) . .
C8 C7 C5 117.43(18) . .
C12 C7 C5 123.54(18) . .
C6 O3 H3 109.5 . .
C11 C12 C7 119.6(2) . .
C11 C12 C6 118.14(19) . .
C7 C12 C6 122.21(18) . .
O1 C5 O4 124.84(19) . .
O1 C5 C7 122.25(19) . .
O4 C5 C7 112.87(17) . .
C10 C11 C12 120.4(2) . .
C10 C11 H11A 119.8 . .
C12 C11 H11A 119.8 . .
O2 C6 O3 123.6(2) . .
O2 C6 C12 118.57(18) . .
O3 C6 C12 117.69(19) . .
C9 C8 C7 120.7(2) . .
C9 C8 H8A 119.6 . .
C7 C8 H8A 119.6 . .
C10 C9 C8 120.0(2) . .
C10 C9 H9A 120.0 . .
C8 C9 H9A 120.0 . .
C9 C10 C11 120.2(2) . .
C9 C10 H10A 119.9 . .
C11 C10 H10A 119.9 . .
C3 N1 C4 119.15(17) . .
N1 C4 C3 120.83(18) . 3_576
N1 C4 C2 117.11(19) . .
C3 C4 C2 122.06(19) 3_576 .
N1 C3 C4 120.02(18) . 3_576
N1 C3 C1 117.10(19) . .
C4 C3 C1 122.87(19) 3_576 .
C4 C2 H2A 109.5 . .
C4 C2 H2B 109.5 . .
H2A C2 H2B 109.5 . .
C4 C2 H2C 109.5 . .
H2A C2 H2C 109.5 . .
H2B C2 H2C 109.5 . .
C3 C1 H1A 109.5 . .
C3 C1 H1B 109.5 . .
H1A C1 H1B 109.5 . .
C3 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
O4 C5 1.317(3) .
O4 H4 0.8200 .
C7 C8 1.391(3) .
C7 C12 1.398(3) .
C7 C5 1.503(3) .
O2 C6 1.256(3) .
O3 C6 1.267(3) .
O3 H3 0.8200 .
O1 C5 1.201(3) .
C12 C11 1.394(3) .
C12 C6 1.492(3) .
C11 C10 1.383(3) .
C11 H11A 0.9300 .
C8 C9 1.390(3) .
C8 H8A 0.9300 .
C9 C10 1.369(4) .
C9 H9A 0.9300 .
C10 H10A 0.9300 .
N1 C3 1.339(3) .
N1 C4 1.341(3) .
C4 C3 1.398(3) 3_576
C4 C2 1.501(3) .
C3 C4 1.398(3) 3_576
C3 C1 1.498(3) .
C2 H2A 0.9600 .
C2 H2B 0.9600 .
C2 H2C 0.9600 .
C1 H1A 0.9600 .
C1 H1B 0.9600 .
C1 H1C 0.9600 .
