#------------------------------------------------------------------------------
#$Date: 2025-08-18 17:20:24 +0300 (Mon, 18 Aug 2025) $
#$Revision: 301776 $
#$URL: file:///home/coder/svn-repositories/cod/cif/1/51/43/1514327.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_1514327
loop_
_publ_author_name
'McCrary, Parker D.'
'Chatel, Gregory'
'Alaniz, Spencer A.'
'Cojocaru, O. Andreea'
'Beasley, Preston A.'
'Flores, Luis A.'
'Kelley, Steven P.'
'Barber, Patrick S.'
'Rogers, Robin D.'
_publ_section_title
;
 Evaluating Ionic Liquids as Hypergolic Fuels: Exploring Reactivity from
 Molecular Structure
;
_journal_issue                   5
_journal_name_full               'Energy & Fuels'
_journal_page_first              3460
_journal_paper_doi               10.1021/ef500264z
_journal_volume                  28
_journal_year                    2014
_chemical_formula_sum            'C3 H7 I N4'
_chemical_formula_weight         226.03
_space_group_crystal_system      monoclinic
_space_group_IT_number           15
_space_group_name_Hall           '-C 2yc'
_space_group_name_H-M_alt        'C 1 2/c 1'
_symmetry_space_group_name_Hall  '-C 2yc'
_symmetry_space_group_name_H-M   'C 1 2/c 1'
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-2013
_cell_angle_alpha                90
_cell_angle_beta                 111.016(16)
_cell_angle_gamma                90
_cell_formula_units_Z            24
_cell_length_a                   29.767(12)
_cell_length_b                   7.814(4)
_cell_length_c                   19.687(8)
_cell_measurement_reflns_used    6097
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      33.09
_cell_measurement_theta_min      2.82
_cell_volume                     4275(3)
_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-2013 (Sheldrick, 2013)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      100(2)
_diffrn_measured_fraction_theta_full 0.987
_diffrn_measured_fraction_theta_max 0.973
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0221
_diffrn_reflns_av_unetI/netI     0.0249
_diffrn_reflns_Laue_measured_fraction_full 0.987
_diffrn_reflns_Laue_measured_fraction_max 0.973
_diffrn_reflns_limit_h_max       45
_diffrn_reflns_limit_h_min       -44
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       29
_diffrn_reflns_limit_l_min       -30
_diffrn_reflns_number            22512
_diffrn_reflns_point_group_measured_fraction_full 0.987
_diffrn_reflns_point_group_measured_fraction_max 0.973
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         33.150
_diffrn_reflns_theta_min         2.175
_exptl_absorpt_coefficient_mu    4.406
_exptl_absorpt_correction_T_max  0.8099
_exptl_absorpt_correction_T_min  0.7196
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'Bruker AXScale'
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    2.107
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       shard
_exptl_crystal_F_000             2544
_exptl_crystal_size_max          0.08
_exptl_crystal_size_mid          0.07
_exptl_crystal_size_min          0.05
_refine_diff_density_max         1.257
_refine_diff_density_min         -0.946
_refine_diff_density_rms         0.120
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.150
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     237
_refine_ls_number_reflns         7932
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.150
_refine_ls_R_factor_all          0.0267
_refine_ls_R_factor_gt           0.0238
_refine_ls_shift/su_max          0.003
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0246P)²+4.0629P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0552
_refine_ls_wR_factor_ref         0.0562
_reflns_Friedel_coverage         0.000
_reflns_number_gt                7375
_reflns_number_total             7932
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            ef500264z_si_002.cif
_cod_data_source_block           C1NTriI
_cod_depositor_comments
'Adding full bibliography for 1514323--1514327.cif.'
_cod_original_cell_volume        4274(3)
_cod_database_code               1514327
#BEGIN Tags that were not found in dictionaries:
_shelx_space_group_comment
; 
The symmetry employed for this shelxl refinement is uniquely defined 
by the following loop, which should always be used as a source of 
symmetry information in preference to the above space-group names. 
They are only intended as comments. 
;
_shelxl_version_number           2013-4
#END Tags that were not found in dictionaries
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y, -z+1/2'
'x+1/2, y+1/2, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y, z-1/2'
'-x+1/2, -y+1/2, -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_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
I1C I 0.23525(2) 0.66510(2) 0.15840(2) 0.01776(3) Uani 1 1 d . .
I1A I 0.42141(2) 1.35124(2) 0.47378(2) 0.01755(3) Uani 1 1 d . .
I1B I 0.41079(2) 0.56466(2) 0.22706(2) 0.01685(3) Uani 1 1 d . .
N1B N 0.32618(6) 0.6443(2) 0.46753(9) 0.0159(3) Uani 1 1 d . .
N1C N 0.32768(6) 0.0125(2) 0.12704(9) 0.0154(3) Uani 1 1 d . .
N1A N 0.51485(6) 1.1026(2) 0.37101(10) 0.0189(3) Uani 1 1 d . .
N2C N 0.29448(7) 0.1389(2) 0.11893(10) 0.0181(3) Uani 1 1 d . .
N2A N 0.53603(7) 0.9816(2) 0.34225(10) 0.0212(3) Uani 1 1 d . .
N2B N 0.35217(6) 0.7889(2) 0.49509(10) 0.0178(3) Uani 1 1 d . .
N4C N 0.35123(6) 0.1463(2) 0.22736(9) 0.0146(3) Uani 1 1 d . .
N4B N 0.33895(6) 0.7597(2) 0.37882(9) 0.0147(3) Uani 1 1 d . .
N4A N 0.48451(6) 0.8657(2) 0.38490(9) 0.0153(3) Uani 1 1 d . .
N6A N 0.45809(7) 0.7478(2) 0.40942(11) 0.0193(3) Uani 1 1 d . .
H6AB H 0.4785(12) 0.690(4) 0.4467(19) 0.029 Uiso 1 1 d . U
H6AA H 0.4457(13) 0.676(4) 0.3770(19) 0.029 Uiso 1 1 d . U
N6B N 0.33955(7) 0.8008(2) 0.31010(10) 0.0199(3) Uani 1 1 d . .
H6BB H 0.3068(13) 0.804(4) 0.2781(18) 0.030 Uiso 1 1 d . U
H6BA H 0.3540(12) 0.730(4) 0.2939(18) 0.030 Uiso 1 1 d . U
N6C N 0.37908(7) 0.1869(2) 0.29955(10) 0.0193(3) Uani 1 1 d . .
H6CB H 0.3889(12) 0.294(4) 0.2966(18) 0.029 Uiso 1 1 d . U
H6CA H 0.3588(13) 0.178(4) 0.3206(19) 0.029 Uiso 1 1 d . U
C3C C 0.31010(7) 0.2191(2) 0.18120(11) 0.0167(3) Uani 1 1 d . .
H3CA H 0.2948 0.3155 0.1928 0.020 Uiso 1 1 calc R U
C3B C 0.35910(7) 0.8567(2) 0.43938(11) 0.0179(3) Uani 1 1 d . .
H3BA H 0.3760 0.9605 0.4408 0.021 Uiso 1 1 calc R U
C3A C 0.51684(8) 0.8377(3) 0.35212(12) 0.0198(4) Uani 1 1 d . .
H3AA H 0.5245 0.7284 0.3382 0.024 Uiso 1 1 calc R U
C5C C 0.36156(7) 0.0165(2) 0.19192(11) 0.0162(3) Uani 1 1 d . .
H5CA H 0.3883 -0.0589 0.2100 0.019 Uiso 1 1 calc R U
C5B C 0.31852(7) 0.6248(2) 0.39823(11) 0.0156(3) Uani 1 1 d . .
H5BA H 0.3018 0.5334 0.3678 0.019 Uiso 1 1 calc R U
C5A C 0.48397(7) 1.0332(3) 0.39652(11) 0.0172(3) Uani 1 1 d . .
H5AA H 0.4649 1.0914 0.4190 0.021 Uiso 1 1 calc R U
C7B C 0.31233(9) 0.5292(3) 0.51419(12) 0.0230(4) Uani 1 1 d . .
H7BA H 0.2940 0.4331 0.4853 0.035 Uiso 1 1 calc R U
H7BB H 0.2923 0.5907 0.5363 0.035 Uiso 1 1 calc R U
H7BC H 0.3412 0.4857 0.5526 0.035 Uiso 1 1 calc R U
C7C C 0.32133(8) -0.1142(3) 0.07004(12) 0.0213(4) Uani 1 1 d . .
H7CA H 0.3527 -0.1618 0.0745 0.032 Uiso 1 1 calc R U
H7CB H 0.3066 -0.0598 0.0223 0.032 Uiso 1 1 calc R U
H7CC H 0.3004 -0.2063 0.0750 0.032 Uiso 1 1 calc R U
C7A C 0.52731(9) 1.2824(3) 0.37103(15) 0.0276(4) Uani 1 1 d . .
H7AA H 0.5145 1.3461 0.4030 0.041 Uiso 1 1 calc R U
H7AB H 0.5134 1.3278 0.3214 0.041 Uiso 1 1 calc R U
H7AC H 0.5624 1.2945 0.3887 0.041 Uiso 1 1 calc R U
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'
I I -0.4742 1.8119 '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
C5B N1B N2B 111.83(16)
C5B N1B C7B 127.34(18)
N2B N1B C7B 120.76(17)
C5C N1C N2C 111.59(16)
C5C N1C C7C 127.38(18)
N2C N1C C7C 120.85(17)
C5A N1A N2A 111.27(17)
C5A N1A C7A 127.82(18)
N2A N1A C7A 120.91(17)
C3C N2C N1C 103.79(17)
C3A N2A N1A 104.04(16)
C3B N2B N1B 103.94(16)
C5C N4C C3C 106.90(17)
C5C N4C N6C 122.77(17)
C3C N4C N6C 130.30(16)
C5B N4B C3B 106.96(16)
C5B N4B N6B 128.48(17)
C3B N4B N6B 124.54(17)
C5A N4A C3A 107.18(17)
C5A N4A N6A 122.93(16)
C3A N4A N6A 129.70(17)
N2C C3C N4C 111.04(17)
N2B C3B N4B 111.07(17)
N2A C3A N4A 110.79(17)
N1C C5C N4C 106.68(17)
N1B C5B N4B 106.19(17)
N1A C5A N4A 106.71(17)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
N1B C5B 1.309(3)
N1B N2B 1.367(2)
N1B C7B 1.447(3)
N1C C5C 1.314(3)
N1C N2C 1.365(2)
N1C C7C 1.457(3)
N1A C5A 1.313(3)
N1A N2A 1.367(2)
N1A C7A 1.452(3)
N2C C3C 1.305(3)
N2A C3A 1.306(3)
N2B C3B 1.300(3)
N4C C5C 1.329(2)
N4C C3C 1.360(3)
N4C N6C 1.401(2)
N4B C5B 1.339(2)
N4B C3B 1.357(3)
N4B N6B 1.397(2)
N4A C5A 1.329(3)
N4A C3A 1.355(2)
N4A N6A 1.405(2)
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 PubChem 139042306
