#------------------------------------------------------------------------------
#$Date: 2019-11-26 10:29:27 +0200 (Tue, 26 Nov 2019) $
#$Revision: 243235 $
#$URL: file:///home/coder/svn-repositories/cod/cif/4/13/34/4133461.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_4133461
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, C2 H8 N'
_chemical_formula_sum            'C3 H8 N4 O6'
_chemical_formula_weight         196.13
_chemical_name_systematic        'dimethylammonium nitroformate'
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2ybc'
_space_group_name_H-M_alt        'P 1 21/c 1'
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     dual
_audit_creation_date             2018-05-01
_audit_creation_method
;
Olex2 1.2
(compiled 2017.08.10 svn.r3458 for OlexSys, GUI svn.r5381)
;
_cell_angle_alpha                90
_cell_angle_beta                 92.666(7)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   7.409(3)
_cell_length_b                   9.031(4)
_cell_length_c                   12.671(5)
_cell_measurement_reflns_used    4974
_cell_measurement_temperature    100(1)
_cell_measurement_theta_max      29.861
_cell_measurement_theta_min      2.752
_cell_volume                     846.9(6)
_computing_cell_refinement       'SAINT v8.37A (Bruker, 2015)'
_computing_data_reduction        'SAINT v8.37A (Bruker, 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      100.0
_diffrn_detector_area_resol_mean 8.3333
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.992
_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  0.0450
_diffrn_reflns_av_unetI/netI     0.0304
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.992
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            19784
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.992
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         30.565
_diffrn_reflns_theta_min         2.752
_diffrn_source                   'fine-focus tube'
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.148
_exptl_absorpt_correction_T_max  0.7461
_exptl_absorpt_correction_T_min  0.6257
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
'SADABS-2016/2 (Bruker,2016/2) was used for absorption correction. wR2(int) was 0.0585 before and 0.0442 after correction. The Ratio of minimum to maximum transmission is 0.8386. The λ/2 correction factor is Not present.'
_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    1.538
_exptl_crystal_description       prism
_exptl_crystal_F_000             408
_exptl_crystal_size_max          0.172
_exptl_crystal_size_mid          0.166
_exptl_crystal_size_min          0.151
_refine_diff_density_max         0.223
_refine_diff_density_min         -0.246
_refine_diff_density_rms         0.049
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.920
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     128
_refine_ls_number_reflns         2578
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.920
_refine_ls_R_factor_all          0.0672
_refine_ls_R_factor_gt           0.0385
_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)+(0.1000P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1120
_refine_ls_wR_factor_ref         0.1330
_reflns_Friedel_coverage         0.000
_reflns_number_gt                1885
_reflns_number_total             2578
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            Comp5.cif
_cod_data_source_block           Comp5
_cod_original_cell_volume        846.8(6)
_cod_database_code               4133461
_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   0.978
_shelx_estimated_absorpt_t_min   0.975
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.5 times of:
  All C(H,H,H) groups
2.a Idealised Me refined as rotating group:
 C2(H2A,H2B,H2C), C1(H1C,H1D,H1E)
;
_olex2_date_sample_completion    2017-03-21
_olex2_date_sample_data_collection 2017-03-21
_olex2_date_sample_submission    2017-03-21
_olex2_submission_original_sample_id AB3_244
_olex2_submission_special_instructions 'No special instructions were received'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -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
O2 O 0.56492(13) 0.55356(10) 0.65393(7) 0.0222(2) Uani 1 1 d .
O3 O 0.73451(13) 0.39138(10) 0.51150(7) 0.0219(2) Uani 1 1 d .
O4 O 0.88151(13) 0.52368(11) 0.39920(7) 0.0237(2) Uani 1 1 d .
O1 O 0.56398(14) 0.79105(10) 0.62011(8) 0.0260(2) Uani 1 1 d .
O6 O 0.88370(14) 0.85886(12) 0.50296(9) 0.0306(3) Uani 1 1 d .
N3 N 0.77999(14) 0.51277(12) 0.47474(8) 0.0174(2) Uani 1 1 d .
O5 O 0.69298(17) 0.80273(13) 0.37508(9) 0.0384(3) Uani 1 1 d .
N2 N 0.61256(14) 0.66125(11) 0.60025(8) 0.0181(2) Uani 1 1 d .
N1 N 0.69666(16) 0.26209(12) 0.71362(9) 0.0197(2) Uani 1 1 d .
N4 N 0.76941(15) 0.77869(12) 0.46102(9) 0.0207(2) Uani 1 1 d .
C3 C 0.72089(18) 0.64412(14) 0.51668(10) 0.0189(3) Uani 1 1 d .
C2 C 0.7394(2) 0.11942(15) 0.66172(11) 0.0258(3) Uani 1 1 d .
H2A H 0.844095 0.132722 0.618154 0.039 Uiso 1 1 calc GR
H2B H 0.635209 0.087350 0.617003 0.039 Uiso 1 1 calc GR
H2C H 0.767145 0.044191 0.715813 0.039 Uiso 1 1 calc GR
C1 C 0.8477(2) 0.32241(16) 0.78171(11) 0.0266(3) Uani 1 1 d .
H1C H 0.880844 0.250789 0.837396 0.040 Uiso 1 1 calc GR
H1D H 0.809773 0.415388 0.813864 0.040 Uiso 1 1 calc GR
H1E H 0.952074 0.340879 0.738844 0.040 Uiso 1 1 calc GR
H1A H 0.665(2) 0.3330(18) 0.6687(14) 0.025(4) Uiso 1 1 d .
H1B H 0.601(3) 0.253(2) 0.7519(14) 0.035(5) Uiso 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
O3 N3 O4 122.69(11)
O3 N3 C3 121.16(11)
O4 N3 C3 116.16(11)
O2 N2 O1 121.86(11)
O2 N2 C3 121.71(11)
O1 N2 C3 116.43(11)
C2 N1 H1A 113.5(11)
C2 N1 H1B 110.7(12)
C1 N1 C2 113.87(11)
C1 N1 H1A 106.2(11)
C1 N1 H1B 108.6(12)
H1A N1 H1B 103.3(17)
O6 N4 O5 124.54(12)
O6 N4 C3 117.81(11)
O5 N4 C3 117.65(11)
N3 C3 N4 116.13(11)
N2 C3 N3 127.16(11)
N2 C3 N4 116.56(11)
N1 C2 H2A 109.5
N1 C2 H2B 109.5
N1 C2 H2C 109.5
H2A C2 H2B 109.5
H2A C2 H2C 109.5
H2B C2 H2C 109.5
N1 C1 H1C 109.5
N1 C1 H1D 109.5
N1 C1 H1E 109.5
H1C C1 H1D 109.5
H1C C1 H1E 109.5
H1D C1 H1E 109.5
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
O2 N2 1.2471(14)
O3 N3 1.2437(14)
O4 N3 1.2484(14)
O1 N2 1.2552(14)
O6 N4 1.2172(15)
N3 C3 1.3794(17)
O5 N4 1.2232(16)
N2 C3 1.3669(17)
N1 C2 1.4874(18)
N1 C1 1.4842(19)
N1 H1A 0.881(17)
N1 H1B 0.88(2)
N4 C3 1.4585(17)
C2 H2A 0.9800
C2 H2B 0.9800
C2 H2C 0.9800
C1 H1C 0.9800
C1 H1D 0.9800
C1 H1E 0.9800
