#------------------------------------------------------------------------------
#$Date: 2019-11-26 10:28:43 +0200 (Tue, 26 Nov 2019) $
#$Revision: 243233 $
#$URL: file:///home/coder/svn-repositories/cod/cif/4/13/34/4133459.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_4133459
loop_
_publ_author_name
'Baxter, Amanda F.'
'Martin, Igor'
'Christe, Karl O.'
'Haiges, Ralf'
_publ_section_title
;
 Formamidinium Nitroformate: An Insensitive RDX Alternative.
;
_journal_issue                   44
_journal_name_full               'Journal of the American Chemical Society'
_journal_page_first              15089
_journal_page_last               15098
_journal_paper_doi               10.1021/jacs.8b10200
_journal_volume                  140
_journal_year                    2018
_chemical_formula_moiety         'C N3 O6, C H5 N2'
_chemical_formula_sum            'C2 H5 N5 O6'
_chemical_formula_weight         195.11
_chemical_name_common            'formamidinium nitroformate'
_chemical_name_systematic        'formamidinium nitroformate'
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_atom_sites_solution_hydrogens   difmap
_atom_sites_solution_primary     dual
_audit_creation_date             2018-04-24
_audit_creation_method
;
Olex2 1.2
(compiled 2017.08.10 svn.r3458 for OlexSys, GUI svn.r5381)
;
_cell_angle_alpha                98.976(11)
_cell_angle_beta                 100.324(11)
_cell_angle_gamma                109.945(10)
_cell_formula_units_Z            2
_cell_length_a                   6.764(4)
_cell_length_b                   7.374(5)
_cell_length_c                   8.058(5)
_cell_measurement_reflns_used    965
_cell_measurement_temperature    100.(2)
_cell_measurement_theta_max      23.9685
_cell_measurement_theta_min      3.0242
_cell_volume                     361.3(4)
_computing_cell_refinement       'SAINT V8.37A (Bruker AXS Inc., 2015)'
_computing_data_reduction        'SAINT V8.37A (Bruker AXS Inc., 2015)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_diffrn_ambient_temperature      99.99
_diffrn_detector_area_resol_mean 8.3333
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.972
_diffrn_measurement_device_type  'Bruker APEX II CCD'
_diffrn_measurement_method       'omega- and phi-scans'
_diffrn_radiation_monochromator  'TRIUMPH curved-crystal'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0861
_diffrn_reflns_av_unetI/netI     0.0946
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.972
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_number            9189
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.972
_diffrn_reflns_theta_full        27.500
_diffrn_reflns_theta_max         30.751
_diffrn_reflns_theta_min         2.643
_diffrn_source                   'fine-focus tube'
_exptl_absorpt_coefficient_mu    0.177
_exptl_absorpt_correction_T_max  0.97
_exptl_absorpt_correction_T_min  0.79
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS V2016/2 (Bruker AXS, 2016)'
_exptl_crystal_colour            'clear light yellow'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.794
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             200
_exptl_crystal_size_max          0.214
_exptl_crystal_size_mid          0.16
_exptl_crystal_size_min          0.149
_refine_diff_density_max         0.297
_refine_diff_density_min         -0.362
_refine_diff_density_rms         0.081
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.967
_refine_ls_hydrogen_treatment    refall
_refine_ls_matrix_type           full
_refine_ls_number_parameters     138
_refine_ls_number_reflns         2204
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.967
_refine_ls_R_factor_all          0.1238
_refine_ls_R_factor_gt           0.0525
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0515P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0989
_refine_ls_wR_factor_ref         0.1255
_reflns_Friedel_coverage         0.000
_reflns_number_gt                1219
_reflns_number_total             2204
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            Comp2.cif
_cod_data_source_block           Comp2
_cod_database_code               4133459
_shelx_shelxl_version_number     2017/1
_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.
;
_shelx_estimated_absorpt_t_max   0.974
_shelx_estimated_absorpt_t_min   0.963
_olex2_refinement_description
;
;
_olex2_date_sample_completion    2016-11-16
_olex2_date_sample_data_collection 2016-11-16
_olex2_date_sample_submission    2016-11-16
_olex2_submission_original_sample_id IM04
_olex2_submission_special_instructions 'No special instructions were received'
loop_
_space_group_symop_operation_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_site_symmetry_order
_atom_site_calc_flag
C1 C 0.4294(3) 0.6054(3) 0.7565(3) 0.0176(5) Uani 1 1 d
C2 C 0.1778(4) 0.9169(3) 0.3020(3) 0.0164(5) Uani 1 1 d
H4A H 0.068(5) 1.112(5) 0.344(4) 0.044(9) Uiso 1 1 d
H4B H -0.074(5) 0.953(4) 0.192(4) 0.042(9) Uiso 1 1 d
H2 H 0.311(4) 0.986(3) 0.395(3) 0.021(6) Uiso 1 1 d
H5A H 0.241(5) 0.694(4) 0.228(4) 0.038(8) Uiso 1 1 d
H5B H 0.037(5) 0.679(4) 0.112(4) 0.045(9) Uiso 1 1 d
N1 N 0.6042(3) 0.6736(3) 0.8976(2) 0.0170(4) Uani 1 1 d
N2 N 0.2924(3) 0.7218(3) 0.7480(2) 0.0158(4) Uani 1 1 d
N3 N 0.3537(3) 0.4291(3) 0.6361(2) 0.0170(4) Uani 1 1 d
N4 N 0.0433(3) 1.0077(3) 0.2804(3) 0.0207(4) Uani 1 1 d
N5 N 0.1496(3) 0.7484(3) 0.2050(3) 0.0205(5) Uani 1 1 d
O1 O 0.7191(2) 0.5750(2) 0.9272(2) 0.0210(4) Uani 1 1 d
O2 O 0.6406(3) 0.8383(2) 0.9937(2) 0.0221(4) Uani 1 1 d
O3 O 0.1494(2) 0.6851(2) 0.8245(2) 0.0224(4) Uani 1 1 d
O4 O 0.3305(3) 0.8487(2) 0.6639(2) 0.0239(4) Uani 1 1 d
O5 O 0.1792(2) 0.3930(2) 0.5261(2) 0.0228(4) Uani 1 1 d
O6 O 0.4517(2) 0.3141(2) 0.6329(2) 0.0234(4) 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
N1 C1 N2 115.84(18)
N3 C1 N1 127.23(18)
N3 C1 N2 116.35(18)
N4 C2 H2 116.6(14)
N5 C2 H2 119.1(14)
N5 C2 N4 124.3(2)
O1 N1 C1 121.15(18)
O1 N1 O2 122.58(18)
O2 N1 C1 116.27(17)
O3 N2 C1 117.66(19)
O3 N2 O4 124.96(18)
O4 N2 C1 117.37(18)
O5 N3 C1 115.22(17)
O6 N3 C1 122.55(18)
O6 N3 O5 122.22(18)
C2 N4 H4A 121(2)
C2 N4 H4B 118.8(18)
H4A N4 H4B 121(3)
C2 N5 H5A 120(2)
C2 N5 H5B 124.7(18)
H5A N5 H5B 115(3)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
C1 N1 1.370(3)
C1 N2 1.462(3)
C1 N3 1.367(3)
C2 H2 0.98(2)
C2 N4 1.304(3)
C2 N5 1.294(3)
N1 O1 1.250(2)
N1 O2 1.253(2)
N2 O3 1.215(2)
N2 O4 1.224(2)
N3 O5 1.260(2)
N3 O6 1.241(2)
N4 H4A 0.80(3)
N4 H4B 0.89(3)
N5 H5A 0.86(3)
N5 H5B 0.90(3)
loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
N1 C1 N2 O3 -85.7(3)
N1 C1 N2 O4 94.4(2)
N1 C1 N3 O5 174.4(2)
N1 C1 N3 O6 -6.9(4)
N2 C1 N1 O1 172.66(19)
N2 C1 N1 O2 -7.2(3)
N2 C1 N3 O5 3.5(3)
N2 C1 N3 O6 -177.78(19)
N3 C1 N1 O1 1.7(3)
N3 C1 N1 O2 -178.2(2)
N3 C1 N2 O3 86.2(3)
N3 C1 N2 O4 -93.7(2)
