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#$Date: 2021-02-05 01:27:14 +0200 (Fri, 05 Feb 2021) $
#$Revision: 261737 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/06/02/7060275.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_7060275
loop_
_publ_author_name
'Gettings, Matthew L.'
'Byrd, Edward F. C.'
'Zeller, Matthias'
'Piercey, Davin'
_publ_section_title
;
 Methyl sydnone imine and its energetic salts
;
_journal_issue                   4
_journal_name_full               'New Journal of Chemistry'
_journal_page_first              2228
_journal_page_last               2236
_journal_paper_doi               10.1039/D0NJ05354F
_journal_volume                  45
_journal_year                    2021
_chemical_absolute_configuration ukn
_chemical_formula_sum            'C3 H4 N4 O2'
_chemical_formula_weight         128.10
_space_group_crystal_system      orthorhombic
_space_group_IT_number           36
_space_group_name_Hall           'C 2c -2'
_space_group_name_H-M_alt        'C m c 21'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-2018/3
_audit_update_record
;
2020-09-23 deposited with the CCDC.	2021-01-11 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   6.1158(7)
_cell_length_b                   9.1928(9)
_cell_length_c                   9.3984(10)
_cell_measurement_reflns_used    3960
_cell_measurement_temperature    150(2)
_cell_measurement_theta_max      33.1430
_cell_measurement_theta_min      4.0027
_cell_volume                     528.39(10)
_computing_cell_refinement       'SAINT V8.40A (Bruker, 2019)'
_computing_data_collection       'Apex3 v2019.1-0 (Bruker, 2019)'
_computing_data_reduction        'SAINT V8.40A (Bruker, 2019)'
_computing_structure_refinement
;  
SHELXL-2018/3 (Sheldrick, 2015, 2018), 
SHELXLE Rev1117 (Hübschle et al., 2011)
;
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      150(2)
_diffrn_detector_area_resol_mean 7.4074
_diffrn_measured_fraction_theta_full 0.993
_diffrn_measured_fraction_theta_max 0.993
_diffrn_measurement_device_type
;
Bruker AXS D8 Quest diffractometer with PhotonII charge-integrating pixel 
array detector (CPAD)
;
_diffrn_measurement_method       'omega and phi scans'
_diffrn_radiation_monochromator  'Triumph curved graphite crystal'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0418
_diffrn_reflns_av_unetI/netI     0.0431
_diffrn_reflns_Laue_measured_fraction_full 0.993
_diffrn_reflns_Laue_measured_fraction_max 0.993
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            4289
_diffrn_reflns_point_group_measured_fraction_full 0.992
_diffrn_reflns_point_group_measured_fraction_max 0.979
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         33.198
_diffrn_reflns_theta_min         4.002
_diffrn_source                   'fine focus sealed tube X-ray source'
_diffrn_source_current           '30 mA'
_diffrn_source_voltage           '50 kV'
_exptl_absorpt_coefficient_mu    0.137
_exptl_absorpt_correction_T_max  0.7465
_exptl_absorpt_correction_T_min  0.6304
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
 SADABS 2016/2: Krause, L., Herbst-Irmer, R., Sheldrick G.M. & Stalke D.,
 J. Appl. Cryst. 48 (2015) 3-10
;
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.610
_exptl_crystal_description       block
_exptl_crystal_F_000             264
_exptl_crystal_size_max          0.310
_exptl_crystal_size_mid          0.220
_exptl_crystal_size_min          0.200
_refine_diff_density_max         0.273
_refine_diff_density_min         -0.223
_refine_diff_density_rms         0.048
_refine_ls_abs_structure_details
;
 Flack x determined using 434 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.1(7)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.066
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     56
_refine_ls_number_reflns         1077
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.066
_refine_ls_R_factor_all          0.0380
_refine_ls_R_factor_gt           0.0342
_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)+(0.0557P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0889
_refine_ls_wR_factor_ref         0.0913
_reflns_Friedel_coverage         0.873
_reflns_Friedel_fraction_full    0.992
_reflns_Friedel_fraction_max     0.964
_reflns_number_gt                989
_reflns_number_total             1077
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d0nj05354f2.cif
_cod_data_source_block           G117c3_MSI_NO2BF4_0m
_cod_depositor_comments
'Adding full bibliography for 7060272--7060278.cif.'
_cod_database_code               7060275
_shelx_shelxl_version_number     2018/3
_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_min   0.959
_shelx_estimated_absorpt_t_max   0.973
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, z+1/2'
'x, -y, z+1/2'
'-x, y, z'
'x+1/2, y+1/2, z'
'-x+1/2, -y+1/2, z+1/2'
'x+1/2, -y+1/2, z+1/2'
'-x+1/2, y+1/2, 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
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
O1 O 0.000000 0.72558(15) -0.12018(15) 0.0265(3) Uani 1 2 d S T P . .
O2 O 0.000000 0.25532(16) -0.0167(2) 0.0333(4) Uani 1 2 d S T P . .
N1 N 0.000000 0.85694(18) -0.05157(17) 0.0263(4) Uani 1 2 d S T P . .
N2 N 0.000000 0.82298(15) 0.08329(16) 0.0217(3) Uani 1 2 d S T P . .
N3 N 0.000000 0.48009(19) -0.07896(16) 0.0259(4) Uani 1 2 d S T P . .
N4 N 0.000000 0.38404(18) 0.0260(2) 0.0267(3) Uani 1 2 d S T P . .
C1 C 0.000000 0.9418(2) 0.1867(2) 0.0292(4) Uani 1 2 d S T P . .
H1A H -0.144379 0.948728 0.231439 0.044 Uiso 0.5 1 calc R U P . .
H1B H 0.033664 1.033517 0.138201 0.044 Uiso 0.5 1 calc R U P . .
H1C H 0.110714 0.922947 0.259789 0.044 Uiso 0.5 1 calc R U P . .
C5 C 0.000000 0.6148(2) -0.02386(17) 0.0212(3) Uani 1 2 d S T P . .
C6 C 0.000000 0.67869(18) 0.10978(19) 0.0216(4) Uani 1 2 d S T P . .
H6 H 0.000000 0.631530 0.199718 0.026 Uiso 1 2 calc R U P . .
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
C5 O1 N1 110.26(14) . . ?
N2 N1 O1 104.27(14) . . ?
N1 N2 C6 114.46(15) . . ?
N1 N2 C1 117.82(15) . . ?
C6 N2 C1 127.72(16) . . ?
N4 N3 C5 109.13(15) . . ?
O2 N4 N3 113.08(19) . . ?
N2 C1 H1A 109.5 . . ?
N2 C1 H1B 109.5 . . ?
H1A C1 H1B 109.5 . . ?
N2 C1 H1C 109.5 . . ?
H1A C1 H1C 109.5 . . ?
H1B C1 H1C 109.5 . . ?
N2 C1 H1A 109.5(3) . 4 ?
H1A C1 H1A 128.6 . 4 ?
H1B C1 H1A 87.4 . 4 ?
H1C C1 H1A 24.3 . 4 ?
N2 C1 H1B 109.5(2) . 4 ?
H1A C1 H1B 87.4 . 4 ?
H1B C1 H1B 24.3 . 4 ?
H1C C1 H1B 128.6 . 4 ?
H1A C1 H1B 109.5 4 4 ?
N2 C1 H1C 109.5(5) . 4 ?
H1A C1 H1C 24.3 . 4 ?
H1B C1 H1C 128.6 . 4 ?
H1C C1 H1C 87.4 . 4 ?
H1A C1 H1C 109.5 4 4 ?
H1B C1 H1C 109.5 4 4 ?
N3 C5 O1 115.67(16) . . ?
N3 C5 C6 137.76(18) . . ?
O1 C5 C6 106.58(15) . . ?
N2 C6 C5 104.43(16) . . ?
N2 C6 H6 127.8 . . ?
C5 C6 H6 127.8 . . ?
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
O1 C5 1.363(2) . ?
O1 N1 1.369(2) . ?
O2 N4 1.250(2) . ?
N1 N2 1.305(2) . ?
N2 C6 1.350(2) . ?
N2 C1 1.462(2) . ?
N3 N4 1.324(2) . ?
N3 C5 1.342(2) . ?
C1 H1A 0.9800 . ?
C1 H1B 0.9800 . ?
C1 H1C 0.9800 . ?
C1 H1A 0.980(13) 4 ?
C1 H1B 0.980(10) 4 ?
C1 H1C 0.98(2) 4 ?
C5 C6 1.386(3) . ?
C6 H6 0.9500 . ?
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
_geom_hbond_publ_flag
C1 H1B O2 0.98 2.51 3.458(3) 161.7 1_565 yes
C6 H6 N3 0.95 2.32 3.269(2) 179.1 2_565 yes
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
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C5 O1 N1 N2 0.000(0) . . . . ?
O1 N1 N2 C6 0.000(0) . . . . ?
O1 N1 N2 C1 180.000(0) . . . . ?
C5 N3 N4 O2 180.000(0) . . . . ?
N4 N3 C5 O1 180.000(0) . . . . ?
N4 N3 C5 C6 0.000(0) . . . . ?
N1 O1 C5 N3 180.000(0) . . . . ?
N1 O1 C5 C6 0.000(0) . . . . ?
N1 N2 C6 C5 0.000(0) . . . . ?
C1 N2 C6 C5 180.000(0) . . . . ?
N3 C5 C6 N2 180.000(0) . . . . ?
O1 C5 C6 N2 0.000(0) . . . . ?
