#------------------------------------------------------------------------------
#$Date: 2019-11-26 10:30:32 +0200 (Tue, 26 Nov 2019) $
#$Revision: 243237 $
#$URL: file:///home/coder/svn-repositories/cod/cif/4/13/34/4133463.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_4133463
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 H6 N'
_chemical_formula_sum            'C2 H6 N4 O6'
_chemical_formula_weight         182.09
_chemical_name_systematic        'methylammonium nitroformate'
_space_group_crystal_system      orthorhombic
_space_group_IT_number           62
_space_group_name_Hall           '-P 2ac 2n'
_space_group_name_H-M_alt        'P n m a'
_symmetry_Int_Tables_number      62
_audit_creation_date             2018-08-20
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3510 for OlexSys, GUI svn.r5506)
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   8.226(2)
_cell_length_b                   8.403(2)
_cell_length_c                   10.367(3)
_cell_measurement_reflns_used    5183
_cell_measurement_temperature    100(1)
_cell_measurement_theta_max      29.756
_cell_measurement_theta_min      3.120
_cell_volume                     716.6(3)
_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  'olex2.refine (Bourhis et al., 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_diffrn_ambient_temperature      99.99
_diffrn_detector_area_resol_mean 8.3333
_diffrn_measured_fraction_theta_full 0.9983
_diffrn_measured_fraction_theta_max 0.9983
_diffrn_measurement_device_type  'Bruker APEX II CCD'
_diffrn_measurement_method       'omega- and phi-scans'
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0403
_diffrn_reflns_av_unetI/netI     0.0146
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            16233
_diffrn_reflns_theta_full        30.4997
_diffrn_reflns_theta_max         30.50
_diffrn_reflns_theta_min         3.12
_exptl_absorpt_coefficient_mu    0.167
_exptl_absorpt_correction_T_max  0.7461
_exptl_absorpt_correction_T_min  0.6248
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
'SADABS-2016/2 (Bruker,2016/2) was used for absorption correction. wR2(int) was 0.0632 before and 0.0496 after correction. The Ratio of minimum to maximum transmission is 0.8374. 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    1.6876
_exptl_crystal_description       prism
_exptl_crystal_F_000             376.3019
_exptl_crystal_size_max          0.418
_exptl_crystal_size_mid          0.286
_exptl_crystal_size_min          0.194
_refine_diff_density_max         0.2813
_refine_diff_density_min         -0.2654
_refine_diff_density_rms         0.0515
_refine_ls_d_res_high            0.7002
_refine_ls_d_res_low             6.5278
_refine_ls_goodness_of_fit_ref   1.0816
_refine_ls_hydrogen_treatment    refall
_refine_ls_matrix_type           full
_refine_ls_number_constraints    1
_refine_ls_number_parameters     106
_refine_ls_number_reflns         1158
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.0816
_refine_ls_R_factor_all          0.0429
_refine_ls_R_factor_gt           0.0350
_refine_ls_shift/su_max          0.0023
_refine_ls_shift/su_mean         0.0005
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0446P)²+0.2260P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0915
_refine_ls_wR_factor_ref         0.0975
_reflns_Friedel_coverage         0.0
_reflns_limit_h_max              11
_reflns_limit_h_min              0
_reflns_limit_k_max              11
_reflns_limit_k_min              0
_reflns_limit_l_max              14
_reflns_limit_l_min              0
_reflns_number_gt                979
_reflns_number_total             1158
_reflns_threshold_expression     I>=2u(I)
_cod_data_source_file            Comp4.cif
_cod_data_source_block           mo_Comp4
_cod_database_code               4133463
_olex2_refinement_description
;
1. Others
 Sof(O2A)=Sof(O1A)=1-FVAR(1)
 Sof(O1)=Sof(O2)=FVAR(1)
 Fixed Sof: N3(0.5) O4(0.5) O3(0.5)
;
_olex2_submission_special_instructions 'No special instructions were received'
loop_
_space_group_symop_id
_space_group_symop_operation_xyz
1 x,y,z
2 x+1/2,-y+1/2,-z+1/2
3 -x,y+1/2,-z
4 -x+1/2,-y,z+1/2
5 -x,-y,-z
6 -x-1/2,y-1/2,z-1/2
7 x,-y-1/2,z
8 x-1/2,y,-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_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_group
O1 O 0.7870(9) 0.5958(8) 0.5245(8) 0.0274(7) Uani 0.50(4) 1 . . . 1
O2 O 0.6182(8) 0.5042(16) 0.3776(9) 0.0289(10) Uani 0.50(4) 1 . . . 1
N1 N 1.10913(15) 0.75 0.55636(11) 0.0229(3) Uani 1.000000 2 S T P .
N2 N 0.67964(10) 0.60533(11) 0.43493(8) 0.0267(2) Uani 1.000000 1 . . . .
C2 C 0.61373(16) 0.75 0.40411(14) 0.0271(3) Uani 1.000000 2 S T P .
C1 C 1.0918(2) 0.75 0.69891(14) 0.0284(3) Uani 1.000000 2 S T P .
N3 N 0.48092(17) 0.7274(6) 0.31148(14) 0.0224(10) Uani 0.500000 1 . . . -1
O4 O 0.35460(18) 0.7977(3) 0.34145(16) 0.0536(9) Uani 0.500000 1 . . . -1
O3 O 0.5022(2) 0.6619(2) 0.20882(14) 0.0366(4) Uani 0.500000 1 . . . -1
H1a H 1.018(3) 0.75 0.516(2) 0.035(5) Uiso 1.000000 2 S T P .
H1b H 1.164(2) 0.835(2) 0.5300(16) 0.050(5) Uiso 1.000000 1 . . . .
H1c H 1.031(2) 0.8444(19) 0.7256(17) 0.056(5) Uiso 1.000000 1 . . . .
H1d H 1.197(3) 0.75 0.739(3) 0.051(6) Uiso 1.000000 2 S T P .
O2A O 0.6147(6) 0.4635(14) 0.3992(9) 0.0250(11) Uani 0.50(4) 1 . . . 2
O1A O 0.8101(13) 0.5936(8) 0.4920(17) 0.0325(17) Uani 0.50(4) 1 . . . 2
loop_
_atom_type_symbol
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_Cromer_Mann_a1
_atom_type_scat_Cromer_Mann_a2
_atom_type_scat_Cromer_Mann_a3
_atom_type_scat_Cromer_Mann_a4
_atom_type_scat_Cromer_Mann_b1
_atom_type_scat_Cromer_Mann_b2
_atom_type_scat_Cromer_Mann_b3
_atom_type_scat_Cromer_Mann_b4
_atom_type_scat_Cromer_Mann_c
_atom_type_scat_source
_atom_type_scat_dispersion_source
H 0.00000 0.00000 0.49300 0.32291 0.14019 0.04081 10.51090 26.12570 3.14236
57.79970 0.0030380000826
'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'
C 0.00347 0.00161 2.31000 1.02000 1.58860 0.86500 20.84390 10.20750 0.56870
51.65120 0.215599998832
'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'
O 0.01158 0.00611 3.04850 2.28680 1.54630 0.86700 13.27710 5.70110 0.32390
32.90890 0.250800013542
'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'
N 0.00653 0.00323 12.21260 3.13220 2.01250 1.16630 0.00570 9.89330 28.99750
0.58260 -11.5290002823
'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'
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
H1a N1 C1 113.5(14) . .
H1b N1 C1 110.8(11) 7_575 .
H1b N1 C1 110.8(11) . .
H1b N1 H1a 107.1(13) 7_575 .
H1b N1 H1a 107.1(13) . .
H1b N1 H1b 107(2) 7_575 .
O2 N2 O1 128.9(7) . .
O1A N2 O2A 113.9(6) . .
N2 C2 N2 125.26(12) 7_575 .
N3 C2 N2 109.44(19) . .
N3 C2 N2 109.44(19) 7_575 7_575
N3 C2 N2 124.3(2) . 7_575
N3 C2 N2 124.3(2) 7_575 .
N3 C2 N3 14.9(4) 7_575 .
H1c C1 N1 109.3(10) 7_575 .
H1c C1 N1 109.3(10) . .
H1c C1 H1c 108(2) 7_575 .
H1d C1 N1 110.4(16) . .
H1d C1 H1c 109.7(12) . .
H1d C1 H1c 109.7(12) . 7_575
O4 N3 C2 113.6(2) . 7_575
O3 N3 C2 121.78(18) . 7_575
O3 N3 O4 124.06(17) . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
O1 N2 1.284(6) .
O2 N2 1.153(8) .
N1 C1 1.4847(19) .
N1 H1a 0.85(2) .
N1 H1b 0.889(18) 7_575
N1 H1b 0.889(18) .
N2 C2 1.3688(12) .
N2 O2A 1.357(9) .
N2 O1A 1.229(5) .
C2 N3 1.467(2) .
C2 N3 1.467(2) 7_575
C1 H1c 0.978(17) .
C1 H1c 0.978(17) 7_575
C1 H1d 0.96(3) .
N3 O4 1.235(3) .
N3 O3 1.211(3) .
