#------------------------------------------------------------------------------
#$Date: 2016-03-26 00:33:52 +0200 (Sat, 26 Mar 2016) $
#$Revision: 180085 $
#$URL: svn://www.crystallography.net/cod/cif/7/05/31/7053132.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_7053132
loop_
_publ_author_name
'Smiglak, Marcin'
'Hines, C. Corey'
'Reichert, W. Matthew'
'Shamshina, Julia L.'
'Beasley, Preston A.'
'McCrary, Parker D.'
'Kelley, Steven P.'
'Rogers, Robin D.'
_publ_section_title
;
 Azolium azolates from reactions of neutral azoles with
 1,3-dimethyl-imidazolium-2-carboxylate, 1,2,3-trimethyl-imidazolium
 hydrogen carbonate, and N,N-dimethyl-pyrrolidinium hydrogen carbonate
;
_journal_issue                   5
_journal_name_full               'New Journal of Chemistry'
_journal_page_first              1461
_journal_paper_doi               10.1039/c3nj00147d
_journal_volume                  37
_journal_year                    2013
_chemical_formula_sum            'C8 H11 N5 O2'
_chemical_formula_weight         209.22
_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                 92.216(4)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   8.1437(17)
_cell_length_b                   10.197(2)
_cell_length_c                   12.090(3)
_cell_measurement_reflns_used    770
_cell_measurement_temperature    173(2)
_cell_measurement_theta_max      26.81
_cell_measurement_theta_min      2.61
_cell_volume                     1003.2(4)
_computing_cell_refinement       'Bruker SAINT'
_computing_data_collection       'Bruker APEX2'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      173(2)
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.959
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_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  0.0330
_diffrn_reflns_av_sigmaI/netI    0.0391
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -7
_diffrn_reflns_number            6968
_diffrn_reflns_theta_full        25.35
_diffrn_reflns_theta_max         28.27
_diffrn_reflns_theta_min         2.61
_exptl_absorpt_coefficient_mu    0.104
_exptl_absorpt_correction_T_max  0.9938
_exptl_absorpt_correction_T_min  0.9845
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SHELX SADABS'
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.385
_exptl_crystal_density_meas      0
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             440
_exptl_crystal_size_max          0.15
_exptl_crystal_size_mid          0.08
_exptl_crystal_size_min          0.06
_refine_diff_density_max         0.204
_refine_diff_density_min         -0.213
_refine_diff_density_rms         0.044
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.090
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     161
_refine_ls_number_reflns         2381
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.090
_refine_ls_R_factor_all          0.0947
_refine_ls_R_factor_gt           0.0581
_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)+(0.0448P)²+0.2783P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1063
_refine_ls_wR_factor_ref         0.1187
_reflns_number_gt                1700
_reflns_number_total             2381
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            c3nj00147d.txt
_cod_data_source_block           '[1,3-diMe-Im][4-NO2-Im]'
_cod_depositor_comments
;
The following automatic conversions were performed:

'_symmetry_cell_setting' value 'Monoclinic' changed to 'monoclinic'
according to /home/saulius/struct/CIF-dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.2 from 2011-04-26.

Automatic conversion script
Id: cif_fix_values 1891 2012-01-12 08:04:46Z andrius 
;
_cod_original_sg_symbol_H-M      P2(1)/n
_cod_database_code               7053132
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
N8 N 0.3158(2) 0.85558(16) 0.01457(16) 0.0456(4) Uani 1 1 d .
N10 N 0.25225(18) 0.63811(15) 0.00088(13) 0.0341(4) Uani 1 1 d .
N13 N 0.42537(18) 0.57955(16) -0.14873(13) 0.0364(4) Uani 1 1 d .
N3 N 0.18334(18) 0.21151(15) 0.01215(13) 0.0343(4) Uani 1 1 d .
N1 N 0.10084(17) 0.33381(15) 0.14406(12) 0.0313(4) Uani 1 1 d .
O1 O 0.37066(19) 0.46617(15) -0.14968(13) 0.0535(4) Uani 1 1 d .
O2 O 0.53428(16) 0.61436(15) -0.21214(11) 0.0474(4) Uani 1 1 d .
C9 C 0.2300(2) 0.75139(19) 0.05153(17) 0.0360(5) Uani 1 1 d .
H9A H 0.161(2) 0.759(2) 0.1136(18) 0.043 Uiso 1 1 d .
C11 C 0.3623(2) 0.67208(18) -0.07577(15) 0.0312(4) Uani 1 1 d .
C12 C 0.4003(3) 0.8035(2) -0.06780(18) 0.0411(5) Uani 1 1 d .
H12A H 0.474(3) 0.853(2) -0.1107(18) 0.049 Uiso 1 1 d .
C2 C 0.1664(2) 0.33439(19) 0.04530(16) 0.0326(4) Uani 1 1 d .
H2A H 0.200(2) 0.410(2) 0.0088(16) 0.039 Uiso 1 1 d .
C5 C 0.0749(2) 0.2061(2) 0.17492(18) 0.0379(5) Uani 1 1 d .
H5A H 0.024(2) 0.184(2) 0.2419(17) 0.045 Uiso 1 1 d .
C4 C 0.1267(2) 0.1300(2) 0.09288(18) 0.0397(5) Uani 1 1 d .
H4A H 0.131(2) 0.038(2) 0.0861(18) 0.048 Uiso 1 1 d .
C7 C 0.2497(3) 0.1693(2) -0.09270(17) 0.0473(5) Uani 1 1 d .
H7A H 0.2372 0.0741 -0.1004 0.071 Uiso 0.50 1 calc PR
H7B H 0.3664 0.1924 -0.0939 0.071 Uiso 0.50 1 calc PR
H7C H 0.1898 0.2131 -0.1541 0.071 Uiso 0.50 1 calc PR
H7D H 0.2918 0.2456 -0.1319 0.071 Uiso 0.50 1 calc PR
H7E H 0.1626 0.1273 -0.1384 0.071 Uiso 0.50 1 calc PR
H7F H 0.3391 0.1066 -0.0781 0.071 Uiso 0.50 1 calc PR
C6 C 0.0607(3) 0.4509(2) 0.20708(19) 0.0400(5) Uani 1 1 d .
H6C H 0.119(3) 0.523(2) 0.179(2) 0.060 Uiso 1 1 d .
H6B H 0.087(3) 0.438(2) 0.286(2) 0.060 Uiso 1 1 d .
H6A H -0.055(3) 0.466(2) 0.2003(19) 0.060 Uiso 1 1 d .
loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
N8 0.0502(10) 0.0353(9) 0.0516(11) -0.0030(8) 0.0064(9) -0.0005(8)
N10 0.0352(8) 0.0345(9) 0.0332(9) -0.0017(7) 0.0095(7) -0.0003(6)
N13 0.0313(8) 0.0476(10) 0.0306(9) 0.0009(8) 0.0058(7) 0.0017(7)
N3 0.0321(8) 0.0374(9) 0.0336(9) -0.0004(7) 0.0037(7) -0.0007(7)
N1 0.0298(8) 0.0350(9) 0.0296(8) 0.0038(7) 0.0060(6) -0.0018(6)
O1 0.0606(10) 0.0422(9) 0.0594(10) -0.0152(8) 0.0246(8) -0.0054(7)
O2 0.0365(8) 0.0706(10) 0.0363(8) 0.0018(7) 0.0146(6) -0.0005(7)
C9 0.0358(10) 0.0390(11) 0.0336(11) -0.0020(9) 0.0055(8) 0.0028(8)
C11 0.0298(9) 0.0366(11) 0.0274(9) 0.0019(8) 0.0030(8) 0.0004(8)
C12 0.0408(11) 0.0398(12) 0.0428(12) 0.0054(9) 0.0056(9) -0.0053(9)
C2 0.0316(9) 0.0357(11) 0.0307(10) 0.0030(9) 0.0032(8) -0.0031(8)
C5 0.0391(11) 0.0384(11) 0.0365(11) 0.0070(9) 0.0067(9) -0.0024(8)
C4 0.0412(11) 0.0355(11) 0.0424(12) 0.0045(10) 0.0034(9) -0.0026(9)
C7 0.0518(13) 0.0559(13) 0.0344(11) -0.0085(10) 0.0056(10) 0.0037(10)
C6 0.0452(12) 0.0390(12) 0.0365(11) -0.0016(9) 0.0104(10) 0.0002(9)
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
C12 N8 C9 102.72(17)
C9 N10 C11 101.47(16)
O1 N13 O2 121.63(16)
O1 N13 C11 119.57(15)
O2 N13 C11 118.80(16)
C2 N3 C4 108.39(16)
C2 N3 C7 125.97(17)
C4 N3 C7 125.64(18)
C2 N1 C5 108.67(16)
C2 N1 C6 124.87(16)
C5 N1 C6 126.44(16)
N10 C9 N8 116.71(18)
N10 C11 C12 110.64(17)
N10 C11 N13 121.64(16)
C12 C11 N13 127.71(17)
N8 C12 C11 108.45(18)
N3 C2 N1 108.56(17)
C4 C5 N1 106.97(17)
C5 C4 N3 107.40(18)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
N8 C12 1.342(3)
N8 C9 1.357(3)
N10 C9 1.323(2)
N10 C11 1.359(2)
N13 O1 1.239(2)
N13 O2 1.2461(19)
N13 C11 1.402(2)
N3 C2 1.324(2)
N3 C4 1.375(3)
N3 C7 1.462(2)
N1 C2 1.327(2)
N1 C5 1.374(2)
N1 C6 1.460(3)
C11 C12 1.378(3)
C5 C4 1.340(3)
