#------------------------------------------------------------------------------
#$Date: 2025-08-21 22:04:39 +0200 (Thu 21 de Aug de 2025) $
#$Revision: 301851 $
#$URL: svn://www.crystallography.net/cod/cif/7/05/28/7052839.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_7052839
loop_
_publ_author_name
'Smiglak, Marcin'
'Hines, C. Corey'
'Reichert, W. Matthew'
'Vincek, Adam S.'
'Katritzky, Alan R.'
'Thrasher, Joseph S.'
'Sun, Luyi'
'McCrary, Parker D.'
'Beasley, Preston A.'
'Kelley, Steven P.'
'Rogers, Robin D.'
_publ_section_title
;
 Synthesis, limitations, and thermal properties of
 energetically-substituted, protonated imidazolium picrate and nitrate
 salts and further comparison with their methylated analogs
;
_journal_issue                   3
_journal_name_full               'New Journal of Chemistry'
_journal_page_first              702
_journal_paper_doi               10.1039/c1nj20677j
_journal_volume                  36
_journal_year                    2012
_chemical_formula_sum            'C10 H7 N7 O11'
_chemical_formula_weight         401.23
_space_group_IT_number           4
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  'P 2yb'
_symmetry_space_group_name_H-M   'P 1 21 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                 93.367(3)
_cell_angle_gamma                90.00
_cell_formula_units_Z            2
_cell_length_a                   6.2866(10)
_cell_length_b                   11.646(2)
_cell_length_c                   10.3067(17)
_cell_measurement_reflns_used    847
_cell_measurement_temperature    173(2)
_cell_measurement_theta_max      23.28
_cell_measurement_theta_min      2.64
_cell_volume                     753.3(2)
_computing_cell_refinement       'Bruker SMART'
_computing_data_collection       'Bruker SMART'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'Bruker SHELXTL'
_diffrn_ambient_temperature      173(2)
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega 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  0.0143
_diffrn_reflns_av_sigmaI/netI    0.0226
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_limit_l_min       -9
_diffrn_reflns_number            3527
_diffrn_reflns_theta_full        23.29
_diffrn_reflns_theta_max         23.29
_diffrn_reflns_theta_min         1.98
_exptl_absorpt_coefficient_mu    0.163
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.769
_exptl_crystal_density_meas      0
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       needle
_exptl_crystal_F_000             408
_exptl_crystal_size_max          0.34
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.12
_refine_diff_density_max         0.100
_refine_diff_density_min         -0.181
_refine_diff_density_rms         0.034
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   -0.1(10)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.506
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     257
_refine_ls_number_reflns         2075
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      0.506
_refine_ls_R_factor_all          0.0255
_refine_ls_R_factor_gt           0.0236
_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)+(0.0505P)²+1.6312P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0558
_refine_ls_wR_factor_ref         0.0581
_reflns_number_gt                1985
_reflns_number_total             2075
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            c1nj20677j.txt
_cod_data_source_block           16a
_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 2.4.1 from 2010-06-29.

Automatic conversion script
Id: cif_fix_values 1715 2011-07-08 13:25:40Z adriana 
;
_cod_original_sg_symbol_H-M      P2(1)
_cod_database_code               7052839
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y+1/2, -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 -0.1651(3) 0.60613(16) 0.09333(17) 0.0237(4) Uani 1 1 d .
N3 N -0.4831(3) 0.68284(16) 0.13296(17) 0.0221(4) Uani 1 1 d .
N4 N -0.3528(3) 0.54014(18) 0.28512(17) 0.0253(4) Uani 1 1 d .
N5 N -0.5195(3) 0.81700(18) -0.04609(18) 0.0297(5) Uani 1 1 d .
N6 N 0.3139(3) 0.52962(18) 0.75480(18) 0.0302(5) Uani 1 1 d .
N7 N 0.9122(3) 0.28100(18) 0.67537(19) 0.0278(5) Uani 1 1 d .
N8 N 0.2866(3) 0.26603(17) 0.37381(18) 0.0282(5) Uani 1 1 d .
O1 O -0.5096(3) 0.55460(14) 0.34677(15) 0.0370(4) Uani 1 1 d .
H1 H 0.068(5) 0.416(3) 0.441(3) 0.055 Uiso 1 1 d .
O2 O -0.2097(3) 0.47094(15) 0.31256(16) 0.0359(4) Uani 1 1 d .
O3 O -0.7022(3) 0.83721(16) -0.01866(17) 0.0411(5) Uani 1 1 d .
O4 O -0.4261(3) 0.86681(15) -0.13084(16) 0.0403(4) Uani 1 1 d .
O5 O 0.1092(2) 0.45147(14) 0.51987(15) 0.0288(4) Uani 1 1 d .
O6 O 0.1827(3) 0.59758(17) 0.70963(18) 0.0470(5) Uani 1 1 d .
O7 O 0.3756(3) 0.52587(17) 0.87006(15) 0.0416(4) Uani 1 1 d .
O8 O 1.0027(2) 0.32548(15) 0.77169(15) 0.0334(4) Uani 1 1 d .
O9 O 0.9888(3) 0.20383(14) 0.61185(17) 0.0343(4) Uani 1 1 d .
C2 C -0.3344(3) 0.6092(2) 0.1703(2) 0.0217(5) Uani 1 1 d .
C4 C -0.4031(4) 0.72979(19) 0.0267(2) 0.0225(5) Uani 1 1 d .
C5 C -0.2088(3) 0.6852(2) -0.0003(2) 0.0246(5) Uani 1 1 d .
H5A H -0.1234 0.7055 -0.0698 0.030 Uiso 1 1 calc R
C6 C 0.0338(3) 0.5390(2) 0.1055(2) 0.0322(5) Uani 1 1 d .
H6A H 0.1226 0.5581 0.0335 0.048 Uiso 1 1 calc R
H6B H 0.0000 0.4569 0.1029 0.048 Uiso 1 1 calc R
H6C H 0.1112 0.5574 0.1882 0.048 Uiso 1 1 calc R
C7 C 0.2988(3) 0.40768(19) 0.5548(2) 0.0221(5) Uani 1 1 d .
C8 C 0.4093(3) 0.44646(19) 0.6683(2) 0.0239(5) Uani 1 1 d .
C9 C 0.6083(3) 0.4064(2) 0.7075(2) 0.0246(5) Uani 1 1 d .
H9A H 0.6805 0.4348 0.7845 0.030 Uiso 1 1 calc R
C10 C 0.7014(3) 0.3242(2) 0.6328(2) 0.0232(5) Uani 1 1 d .
O10 O 0.3623(3) 0.18044(16) 0.32710(17) 0.0415(5) Uani 1 1 d .
O11 O 0.1184(2) 0.31016(15) 0.32940(15) 0.0341(4) Uani 1 1 d .
C11 C 0.5981(3) 0.2775(2) 0.5232(2) 0.0227(5) Uani 1 1 d .
H11A H 0.6622 0.2187 0.4749 0.027 Uiso 1 1 calc R
C12 C 0.3978(3) 0.3196(2) 0.4865(2) 0.0222(5) Uani 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
C5 N1 C2 105.35(17)
C5 N1 C6 123.96(18)
C2 N1 C6 130.61(19)
C2 N3 C4 102.16(18)
O1 N4 O2 125.2(2)
O1 N4 C2 117.31(19)
O2 N4 C2 117.53(19)
O3 N5 O4 124.7(2)
O3 N5 C4 118.19(19)
O4 N5 C4 117.07(19)
O6 N6 O7 124.2(2)
O6 N6 C8 119.27(18)
O7 N6 C8 116.54(19)
O9 N7 O8 124.19(19)
O9 N7 C10 117.98(19)
O8 N7 C10 117.8(2)
O10 N8 O11 122.62(19)
O10 N8 C12 119.01(18)
O11 N8 C12 118.37(19)
N3 C2 N1 114.4(2)
N3 C2 N4 121.10(19)
N1 C2 N4 124.47(19)
N3 C4 C5 113.0(2)
N3 C4 N5 120.5(2)
C5 C4 N5 126.5(2)
N1 C5 C4 105.09(18)
O5 C7 C8 119.8(2)
O5 C7 C12 124.07(19)
C8 C7 C12 116.11(19)
C9 C8 C7 122.4(2)
C9 C8 N6 116.27(19)
C7 C8 N6 121.33(19)
C8 C9 C10 118.7(2)
C11 C10 C9 122.4(2)
C11 C10 N7 119.0(2)
C9 C10 N7 118.5(2)
C10 C11 C12 117.5(2)
C11 C12 C7 122.86(19)
C11 C12 N8 116.9(2)
C7 C12 N8 120.23(18)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
N1 C5 1.350(3)
N1 C2 1.365(3)
N1 C6 1.474(3)
N3 C2 1.310(3)
N3 C4 1.348(3)
N4 O1 1.216(2)
N4 O2 1.228(3)
N4 C2 1.441(3)
N5 O3 1.221(2)
N5 O4 1.227(2)
N5 C4 1.437(3)
N6 O6 1.216(3)
N6 O7 1.229(2)
N6 C8 1.468(3)
N7 O9 1.227(3)
N7 O8 1.229(3)
N7 C10 1.461(3)
N8 O10 1.216(3)
N8 O11 1.239(2)
N8 C12 1.459(3)
O5 C7 1.326(3)
C4 C5 1.370(3)
C7 C8 1.400(3)
C7 C12 1.410(3)
C8 C9 1.374(3)
C9 C10 1.381(3)
C10 C11 1.380(3)
C11 C12 1.384(3)
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 PubChem 139176112
