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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/7/06/02/7060272.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_7060272
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_formula_moiety         'C3 H6 N3 O, N O3'
_chemical_formula_sum            'C3 H6 N4 O4'
_chemical_formula_weight         162.12
_space_group_crystal_system      monoclinic
_space_group_IT_number           11
_space_group_name_Hall           '-P 2yb'
_space_group_name_H-M_alt        'P 1 21/m 1'
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-2018/3
_audit_update_record
;
2020-08-24 deposited with the CCDC.	2021-01-11 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 91.390(5)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   5.7481(6)
_cell_length_b                   5.8420(7)
_cell_length_c                   9.9504(11)
_cell_measurement_reflns_used    2359
_cell_measurement_temperature    150(2)
_cell_measurement_theta_max      78.9749
_cell_measurement_theta_min      7.7099
_cell_volume                     334.04(6)
_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 0.986
_diffrn_measured_fraction_theta_max 0.949
_diffrn_measurement_device_type
;
Bruker AXS D8 Quest diffractometer with PhotonIII_C14 charge-integrating and 
photon counting pixel array detector
;
_diffrn_measurement_method       'omega and phi scans'
_diffrn_radiation_monochromator  'laterally graded multilayer (Goebel) mirror'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0326
_diffrn_reflns_av_unetI/netI     0.0328
_diffrn_reflns_Laue_measured_fraction_full 0.986
_diffrn_reflns_Laue_measured_fraction_max 0.949
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            2988
_diffrn_reflns_point_group_measured_fraction_full 0.986
_diffrn_reflns_point_group_measured_fraction_max 0.949
_diffrn_reflns_theta_full        67.679
_diffrn_reflns_theta_max         79.262
_diffrn_reflns_theta_min         7.710
_diffrn_source                   'I-mu-S microsource X-ray tube'
_diffrn_source_current           '1.0 mA'
_diffrn_source_voltage           '50 kV'
_exptl_absorpt_coefficient_mu    1.306
_exptl_absorpt_correction_T_max  0.7542
_exptl_absorpt_correction_T_min  0.6329
_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            colourless
_exptl_crystal_density_diffrn    1.612
_exptl_crystal_description       block
_exptl_crystal_F_000             168
_exptl_crystal_size_max          0.150
_exptl_crystal_size_mid          0.130
_exptl_crystal_size_min          0.090
_refine_diff_density_max         0.188
_refine_diff_density_min         -0.293
_refine_diff_density_rms         0.050
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.146
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     72
_refine_ls_number_reflns         764
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.146
_refine_ls_R_factor_all          0.0377
_refine_ls_R_factor_gt           0.0356
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0538P)²+0.0917P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1017
_refine_ls_wR_factor_ref         0.1045
_reflns_Friedel_coverage         0.000
_reflns_number_gt                711
_reflns_number_total             764
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d0nj05354f2.cif
_cod_data_source_block           G117_MSI_NO3_0m
_cod_depositor_comments
'Adding full bibliography for 7060272--7060278.cif.'
_cod_original_sg_symbol_H-M      'P 21/m'
_cod_database_code               7060272
_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   0.828
_shelx_estimated_absorpt_t_max   0.891
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z'
'-x, -y, -z'
'x, -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 0.2439(2) 0.250000 0.29026(13) 0.0223(3) Uani 1 2 d S T P . .
O2 O 0.8631(2) 0.250000 0.75147(13) 0.0242(4) Uani 1 2 d S T P . .
O3 O 0.6183(2) 0.250000 0.58335(14) 0.0335(4) Uani 1 2 d S T P . .
O4 O 0.4914(3) 0.250000 0.78635(15) 0.0339(4) Uani 1 2 d S T P . .
N1 N 0.1396(3) 0.250000 0.16287(16) 0.0240(4) Uani 1 2 d S T P . .
N2 N -0.0807(3) 0.250000 0.18624(15) 0.0218(4) Uani 1 2 d S T P . .
N3 N 0.1429(3) 0.250000 0.51217(16) 0.0225(4) Uani 1 2 d S T P . .
H3A H 0.296(5) 0.250000 0.535(2) 0.027 Uiso 1 2 d S U P . .
H3B H 0.033(4) 0.250000 0.571(3) 0.027 Uiso 1 2 d S U P . .
N4 N 0.6555(3) 0.250000 0.70870(16) 0.0207(4) Uani 1 2 d S T P . .
C1 C -0.1347(3) 0.250000 0.31674(18) 0.0220(4) Uani 1 2 d S T P . .
H1 H -0.285332 0.250000 0.353916 0.026 Uiso 1 2 calc R U P . .
C2 C 0.0778(3) 0.250000 0.38510(17) 0.0192(4) Uani 1 2 d S T P . .
C3 C -0.2472(4) 0.250000 0.0713(2) 0.0325(5) Uani 1 2 d S T P . .
H3C H -0.164420 0.217972 -0.011556 0.049 Uiso 0.5 1 calc R U P . .
H3D H -0.322587 0.400144 0.064226 0.049 Uiso 0.5 1 calc R U P . .
H3E H -0.365475 0.131884 0.084774 0.049 Uiso 0.5 1 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 0.0181 0.0091 '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 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 '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
C2 O1 N1 109.79(14) . . ?
N2 N1 O1 103.82(14) . . ?
N1 N2 C1 115.09(16) . . ?
N1 N2 C3 118.75(16) . . ?
C1 N2 C3 126.16(17) . . ?
C2 N3 H3A 120.0(16) . . ?
C2 N3 H3B 117.0(16) . . ?
H3A N3 H3B 123(2) . . ?
O4 N4 O2 121.45(16) . . ?
O4 N4 O3 120.39(16) . . ?
O2 N4 O3 118.16(15) . . ?
N2 C1 C2 104.71(16) . . ?
N2 C1 H1 127.6 . . ?
C2 C1 H1 127.6 . . ?
N3 C2 O1 118.77(17) . . ?
N3 C2 C1 134.65(18) . . ?
O1 C2 C1 106.58(15) . . ?
N2 C3 H3C 109.5 . . ?
N2 C3 H3D 109.5 . . ?
H3C C3 H3D 109.5 . . ?
N2 C3 H3E 109.5 . . ?
H3C C3 H3E 109.5 . . ?
H3D C3 H3E 109.5 . . ?
N2 C3 H3C 109.5(2) . 4_565 ?
N2 C3 H3D 109.5(3) . 4_565 ?
H3C C3 H3D 109.5 4_565 4_565 ?
N2 C3 H3E 109.5(5) . 4_565 ?
H3C C3 H3E 109.5 4_565 4_565 ?
H3D C3 H3E 109.5 4_565 4_565 ?
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 C2 1.359(2) . ?
O1 N1 1.389(2) . ?
O2 N4 1.257(2) . ?
O3 N4 1.260(2) . ?
O4 N4 1.234(2) . ?
N1 N2 1.293(2) . ?
N2 C1 1.342(2) . ?
N2 C3 1.473(2) . ?
N3 C2 1.310(2) . ?
N3 H3A 0.90(3) . ?
N3 H3B 0.87(3) . ?
C1 C2 1.383(3) . ?
C1 H1 0.9500 . ?
C3 H3C 0.9800 . ?
C3 H3D 0.9800 . ?
C3 H3E 0.9800 . ?
C3 H3C 0.980(11) 4_565 ?
C3 H3D 0.980(16) 4_565 ?
C3 H3E 0.98(3) 4_565 ?
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
N3 H3A O3 0.90(3) 1.90(3) 2.806(2) 180(2) . yes
N3 H3B O2 0.87(3) 2.06(3) 2.905(2) 162(2) 1_455 yes
N3 H3B O3 0.87(3) 2.39(3) 3.114(2) 141(2) 1_455 yes
C1 H1 O3 0.95 2.36 3.039(2) 127.9 1_455 yes
C3 H3C O2 0.98 2.37 3.260(3) 150.0 1_454 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
C2 O1 N1 N2 0.000(0) . . . . ?
O1 N1 N2 C1 0.000(0) . . . . ?
O1 N1 N2 C3 180.000(0) . . . . ?
N1 N2 C1 C2 0.000(0) . . . . ?
C3 N2 C1 C2 180.000(0) . . . . ?
N1 O1 C2 N3 180.000(0) . . . . ?
N1 O1 C2 C1 0.000(0) . . . . ?
N2 C1 C2 N3 180.000(0) . . . . ?
N2 C1 C2 O1 0.000(0) . . . . ?
