#------------------------------------------------------------------------------
#$Date: 2025-08-21 22:04:39 +0200 (Thu 21 de Aug de 2025) $
#$Revision: 301851 $
#$URL: svn://www.crystallography.net/cod/cif/7/05/28/7052837.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_7052837
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            'C5 H9 N3 O3'
_chemical_formula_weight         159.15
_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                 111.871(3)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   7.8630(14)
_cell_length_b                   13.001(2)
_cell_length_c                   7.9711(14)
_cell_measurement_reflns_used    956
_cell_measurement_temperature    173(2)
_cell_measurement_theta_max      23.28
_cell_measurement_theta_min      3.13
_cell_volume                     756.2(2)
_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 1.000
_diffrn_measured_fraction_theta_max 1.000
_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  0.0162
_diffrn_reflns_av_sigmaI/netI    0.0163
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -5
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       7
_diffrn_reflns_limit_l_min       -8
_diffrn_reflns_number            3424
_diffrn_reflns_theta_full        23.28
_diffrn_reflns_theta_max         23.28
_diffrn_reflns_theta_min         3.11
_exptl_absorpt_coefficient_mu    0.116
_exptl_absorpt_correction_T_max  0.9931
_exptl_absorpt_correction_T_min  0.9638
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SHELX SADABS'
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.398
_exptl_crystal_density_meas      0
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       fragment
_exptl_crystal_F_000             336
_exptl_crystal_size_max          0.32
_exptl_crystal_size_mid          0.24
_exptl_crystal_size_min          0.06
_refine_diff_density_max         0.118
_refine_diff_density_min         -0.259
_refine_diff_density_rms         0.038
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.068
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     105
_refine_ls_number_reflns         1092
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.068
_refine_ls_R_factor_all          0.0412
_refine_ls_R_factor_gt           0.0343
_refine_ls_shift/su_max          0.045
_refine_ls_shift/su_mean         0.003
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0490P)²+0.2509P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0877
_refine_ls_wR_factor_ref         0.0918
_reflns_number_gt                947
_reflns_number_total             1092
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            c1nj20677j.txt
_cod_data_source_block           2b
_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)/n
_cod_database_code               7052837
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
O1 O 0.25364(18) 1.56243(11) 0.40884(19) 0.0492(4) Uani 1 1 d .
O2 O 0.43216(18) 1.57380(10) 0.25831(18) 0.0437(4) Uani 1 1 d .
O3 O 0.31264(17) 1.42781(9) 0.28164(19) 0.0418(4) Uani 1 1 d .
N1 N 0.78620(19) 1.29400(10) 0.07419(18) 0.0297(4) Uani 1 1 d .
N3 N 0.5653(2) 1.34081(11) 0.1539(2) 0.0347(4) Uani 1 1 d .
H3A H 0.491(3) 1.3789(15) 0.199(3) 0.042 Uiso 1 1 d .
N4 N 0.33347(19) 1.52291(11) 0.31726(19) 0.0313(4) Uani 1 1 d .
C2 C 0.7212(2) 1.37186(13) 0.1405(2) 0.0283(4) Uani 1 1 d .
C4 C 0.5300(3) 1.24107(14) 0.0934(3) 0.0386(5) Uani 1 1 d .
H4A H 0.4275 1.2006 0.0878 0.046 Uiso 1 1 calc R
C5 C 0.6687(3) 1.21178(13) 0.0436(2) 0.0345(5) Uani 1 1 d .
H5A H 0.6826 1.1466 -0.0038 0.041 Uiso 1 1 calc R
C6 C 0.9488(2) 1.29708(14) 0.0266(3) 0.0366(5) Uani 1 1 d .
H6A H 1.0426 1.3405 0.1133 0.055 Uiso 1 1 calc R
H6B H 0.9159 1.3255 -0.0953 0.055 Uiso 1 1 calc R
H6C H 0.9970 1.2273 0.0300 0.055 Uiso 1 1 calc R
C7 C 0.8026(3) 1.47527(13) 0.1871(3) 0.0386(5) Uani 1 1 d .
H7A H 0.9294 1.4690 0.2731 0.058 Uiso 1 1 calc R
H7B H 0.7315 1.5156 0.2420 0.058 Uiso 1 1 calc R
H7C H 0.8010 1.5099 0.0774 0.058 Uiso 1 1 calc R
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
O1 0.0454(8) 0.0552(9) 0.0534(9) -0.0046(7) 0.0259(7) 0.0148(7)
O2 0.0471(8) 0.0385(8) 0.0488(8) 0.0040(6) 0.0217(7) -0.0075(6)
O3 0.0440(8) 0.0296(7) 0.0571(9) -0.0047(6) 0.0248(7) -0.0047(6)
N1 0.0314(8) 0.0285(8) 0.0297(8) 0.0017(6) 0.0120(6) 0.0003(6)
N3 0.0364(9) 0.0354(9) 0.0377(9) -0.0013(7) 0.0200(7) -0.0001(7)
N4 0.0260(8) 0.0347(9) 0.0297(8) 0.0020(6) 0.0062(7) 0.0050(6)
C2 0.0307(9) 0.0290(9) 0.0253(9) 0.0016(7) 0.0103(7) 0.0017(7)
C4 0.0422(11) 0.0340(10) 0.0433(11) -0.0015(8) 0.0202(9) -0.0098(8)
C5 0.0439(11) 0.0242(9) 0.0357(10) -0.0010(7) 0.0152(9) -0.0043(8)
C6 0.0341(10) 0.0372(10) 0.0429(11) -0.0002(8) 0.0195(9) 0.0023(8)
C7 0.0412(11) 0.0325(10) 0.0436(11) -0.0057(8) 0.0177(9) -0.0029(8)
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
C2 N1 C5 109.29(14)
C2 N1 C6 125.78(14)
C5 N1 C6 124.75(15)
C2 N3 C4 109.20(16)
O2 N4 O1 121.95(15)
O2 N4 O3 118.95(14)
O1 N4 O3 119.09(15)
N1 C2 N3 107.62(15)
N1 C2 C7 126.81(15)
N3 C2 C7 125.55(15)
C5 C4 N3 106.88(17)
C4 C5 N1 107.01(15)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
O1 N4 1.2379(19)
O2 N4 1.2379(19)
O3 N4 1.2656(18)
N1 C2 1.329(2)
N1 C5 1.374(2)
N1 C6 1.464(2)
N3 C2 1.333(2)
N3 C4 1.375(2)
C2 C7 1.476(2)
C4 C5 1.347(3)
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 PubChem 118062462
