#------------------------------------------------------------------------------
#$Date: 2025-08-21 22:04:39 +0200 (Thu 21 de Aug de 2025) $
#$Revision: 301851 $
#$URL: svn://www.crystallography.net/cod/cif/7/05/26/7052652.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_7052652
loop_
_publ_author_name
'Drab, David M.'
'Smiglak, Marcin'
'Shamshina, Julia L.'
'Kelley, Steven P.'
'Schneider, Stefan'
'Hawkins, Tommy W.'
'Rogers, Robin D.'
_publ_section_title
;
 Synthesis of N-cyanoalkyl-functionalized imidazolium nitrate and
 dicyanamide ionic liquids with a comparison of their thermal
 properties for energetic applications
;
_journal_issue                   8
_journal_name_full               'New Journal of Chemistry'
_journal_page_first              1701
_journal_paper_doi               10.1039/c0nj00889c
_journal_volume                  35
_journal_year                    2011
_chemical_formula_sum            'C6 H8 N4 O3'
_chemical_formula_weight         184.16
_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                93.588(3)
_cell_angle_beta                 108.321(2)
_cell_angle_gamma                112.598(2)
_cell_formula_units_Z            4
_cell_length_a                   8.7192(13)
_cell_length_b                   9.8611(14)
_cell_length_c                   11.1363(16)
_cell_measurement_reflns_used    3116
_cell_measurement_temperature    173(2)
_cell_measurement_theta_max      27.85
_cell_measurement_theta_min      2.29
_cell_volume                     820.6(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, 2008)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      173(2)
_diffrn_measured_fraction_theta_full 0.895
_diffrn_measured_fraction_theta_max 0.895
_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  0.0196
_diffrn_reflns_av_sigmaI/netI    0.0331
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            5693
_diffrn_reflns_theta_full        28.31
_diffrn_reflns_theta_max         28.31
_diffrn_reflns_theta_min         2.69
_exptl_absorpt_coefficient_mu    0.122
_exptl_absorpt_correction_T_max  0.898
_exptl_absorpt_correction_T_min  0.69940
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS, Sheldrick, 2002'
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.491
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    none
_exptl_crystal_description       rod
_exptl_crystal_F_000             384
_exptl_crystal_size_max          0.64
_exptl_crystal_size_mid          0.17
_exptl_crystal_size_min          0.14
_refine_diff_density_max         0.443
_refine_diff_density_min         -0.328
_refine_diff_density_rms         0.070
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.769
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     235
_refine_ls_number_reflns         3666
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.769
_refine_ls_R_factor_all          0.0648
_refine_ls_R_factor_gt           0.0514
_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)+(0.1372P)²+1.1817P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1594
_refine_ls_wR_factor_ref         0.1742
_reflns_number_gt                2956
_reflns_number_total             3666
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            c0nj00889c.txt
_cod_data_source_block           4[NO3]
_cod_depositor_comments
;
The following automatic conversions were performed:

'_symmetry_cell_setting' value 'Triclinic' changed to 'triclinic'
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 

The following automatic conversions were performed:

'_exptl_crystal_density_meas' value 'not measured' was changed to '?'
- the value is perceived as not measured.

Automatic conversion script
Id: cif_fix_values 3008 2015-01-20 13:52:24Z robertas 
;
_cod_original_sg_symbol_H-M      P-1
_cod_database_code               7052652
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
_atom_site_disorder_assembly
_atom_site_disorder_group
O1B O 0.7187(2) 0.2900(2) -0.06307(17) 0.0359(4) Uani 1 1 d . . .
O2B O 0.9805(2) 0.3054(2) -0.04217(18) 0.0383(4) Uani 1 1 d . . .
O3B O 0.8474(2) 0.18969(19) 0.08110(15) 0.0326(4) Uani 1 1 d . . .
O1A O 0.7311(2) 0.4983(2) 0.21665(18) 0.0401(4) Uani 1 1 d . . .
O2A O 0.5073(2) 0.53011(19) 0.23450(16) 0.0338(4) Uani 1 1 d . . .
O3A O 0.6209(2) 0.40361(17) 0.35766(14) 0.0294(4) Uani 1 1 d . . .
N1B N 0.3358(2) 0.19277(18) 0.05073(15) 0.0206(4) Uani 1 1 d . . .
N1A N 0.1182(2) 0.41996(18) 0.33743(16) 0.0201(4) Uani 1 1 d . . .
N3B N 0.4434(2) 0.07446(18) 0.18491(16) 0.0209(4) Uani 1 1 d . . .
N3A N 0.2050(2) 0.27347(19) 0.44750(16) 0.0221(4) Uani 1 1 d . . .
N8B N 0.0924(3) 0.1003(2) -0.27078(19) 0.0350(5) Uani 1 1 d . . .
N8A N 0.2566(3) 0.7989(2) 0.39455(19) 0.0333(4) Uani 1 1 d . . .
N9B N 0.8491(2) 0.26200(19) -0.00815(16) 0.0230(4) Uani 1 1 d . . .
N9A N 0.6208(2) 0.47795(18) 0.27030(16) 0.0220(4) Uani 1 1 d . . .
C2B C 0.4732(3) 0.1568(2) 0.09801(19) 0.0214(4) Uani 1 1 d . . .
H2BA H 0.5745 0.1854 0.0736 0.026 Uiso 1 1 calc R . .
C2A C 0.2448(3) 0.3700(2) 0.37190(19) 0.0214(4) Uani 1 1 d . . .
H2AA H 0.3455 0.3985 0.3468 0.026 Uiso 1 1 calc R . .
C4B C 0.2822(3) 0.0564(2) 0.19343(19) 0.0230(4) Uani 1 1 d . . .
H4BA H 0.2289 0.0022 0.2482 0.028 Uiso 1 1 calc R . .
C4A C 0.0500(3) 0.2627(2) 0.46247(19) 0.0234(4) Uani 1 1 d . . .
H4AA H -0.0075 0.2020 0.5122 0.028 Uiso 1 1 calc R . .
C5B C 0.2145(3) 0.1304(2) 0.10915(19) 0.0216(4) Uani 1 1 d . . .
H5BA H 0.1047 0.1379 0.0933 0.026 Uiso 1 1 calc R . .
C5A C -0.0052(3) 0.3539(2) 0.39368(19) 0.0225(4) Uani 1 1 d . . .
H5AA H -0.1085 0.3698 0.3854 0.027 Uiso 1 1 calc R . .
C6B C 0.3194(3) 0.2809(2) -0.04914(19) 0.0247(4) Uani 1 1 d . . .
H6BA H 0.4374 0.3354 -0.0558 0.030 Uiso 1 1 calc R . .
H6BB H 0.2784 0.3558 -0.0257 0.030 Uiso 1 1 calc R . .
C6A C 0.1146(3) 0.5277(2) 0.25327(19) 0.0242(4) Uani 1 1 d . . .
H6AA H -0.0103 0.5008 0.1964 0.029 Uiso 1 1 calc R . .
H6AB H 0.1827 0.5241 0.1978 0.029 Uiso 1 1 calc R . .
C7B C 0.1902(3) 0.1808(2) -0.1751(2) 0.0258(4) Uani 1 1 d . . .
C7A C 0.1936(3) 0.6813(2) 0.3320(2) 0.0243(4) Uani 1 1 d . . .
C9B C 0.5672(3) 0.0194(3) 0.2634(2) 0.0313(5) Uani 1 1 d . . .
H9BA H 0.6717 0.0481 0.2383 0.047 Uiso 1 1 calc R . .
H9BB H 0.5074 -0.0902 0.2495 0.047 Uiso 1 1 calc R . .
H9BC H 0.6055 0.0636 0.3550 0.047 Uiso 1 1 calc R . .
C9A C 0.3122(3) 0.1944(3) 0.5062(2) 0.0296(5) Uani 1 1 d . . .
H9AA H 0.4148 0.2217 0.4789 0.044 Uiso 1 1 calc R . .
H9AB H 0.2389 0.0857 0.4782 0.044 Uiso 1 1 calc R . .
H9AC H 0.3547 0.2229 0.6006 0.044 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
_geom_angle_publ_flag
C2B N1B C5B 109.06(16) . . ?
C2B N1B C6B 124.08(17) . . ?
C5B N1B C6B 126.84(17) . . ?
C2A N1A C5A 109.17(16) . . ?
C2A N1A C6A 124.29(17) . . ?
C5A N1A C6A 126.54(17) . . ?
C2B N3B C4B 109.00(16) . . ?
C2B N3B C9B 124.87(18) . . ?
C4B N3B C9B 126.05(18) . . ?
C2A N3A C4A 108.90(17) . . ?
C2A N3A C9A 124.72(18) . . ?
C4A N3A C9A 126.37(18) . . ?
O2B N9B O1B 119.94(17) . . ?
O2B N9B O3B 120.02(18) . . ?
O1B N9B O3B 120.04(17) . . ?
O1A N9A O2A 119.38(17) . . ?
O1A N9A O3A 120.40(17) . . ?
O2A N9A O3A 120.20(17) . . ?
N3B C2B N1B 108.08(17) . . ?
N3A C2A N1A 107.92(17) . . ?
C5B C4B N3B 107.21(17) . . ?
C5A C4A N3A 107.54(18) . . ?
C4B C5B N1B 106.65(17) . . ?
C4A C5A N1A 106.47(18) . . ?
N1B C6B C7B 109.92(16) . . ?
N1A C6A C7A 110.13(16) . . ?
N8B C7B C6B 177.9(2) . . ?
N8A C7A C6A 178.7(2) . . ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O1B N9B 1.253(2) . ?
O2B N9B 1.247(2) . ?
O3B N9B 1.260(2) . ?
O1A N9A 1.245(2) . ?
O2A N9A 1.254(2) . ?
O3A N9A 1.254(2) . ?
N1B C2B 1.339(3) . ?
N1B C5B 1.379(2) . ?
N1B C6B 1.459(2) . ?
N1A C2A 1.335(3) . ?
N1A C5A 1.382(3) . ?
N1A C6A 1.463(2) . ?
N3B C2B 1.326(3) . ?
N3B C4B 1.382(3) . ?
N3B C9B 1.463(3) . ?
N3A C2A 1.329(3) . ?
N3A C4A 1.378(3) . ?
N3A C9A 1.466(3) . ?
N8B C7B 1.138(3) . ?
N8A C7A 1.141(3) . ?
C4B C5B 1.353(3) . ?
C4A C5A 1.347(3) . ?
C6B C7B 1.479(3) . ?
C6A C7A 1.480(3) . ?
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 PubChem 139175997
