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#$Date: 2021-05-15 07:01:30 +0300 (Sat, 15 May 2021) $
#$Revision: 265240 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/24/28/7242871.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_7242871
loop_
_publ_author_name
'Wozniak, Dominique R.'
'Zeller, Matthias'
'Byrd, Edward F. C.'
'Piercey, Davin G.'
_publ_section_title
;
 3-Methyl-1,2,3-triazolium-1N-dinitromethylylide and the strategy of
 zwitterionic dinitromethyl groups in energetic materials design
;
_journal_issue                   29
_journal_name_full               'RSC Advances'
_journal_page_first              17710
_journal_page_last               17714
_journal_paper_doi               10.1039/D1RA00953B
_journal_volume                  11
_journal_year                    2021
_chemical_formula_sum            'C4 H5 N5 O4'
_chemical_formula_weight         187.13
_space_group_crystal_system      orthorhombic
_space_group_IT_number           64
_space_group_name_Hall           '-C 2ac 2'
_space_group_name_H-M_alt        'C m c e'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-2018/3
_audit_update_record
;
2020-12-09 deposited with the CCDC.	2021-04-28 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   7.7002(7)
_cell_length_b                   14.3978(16)
_cell_length_c                   12.7602(11)
_cell_measurement_reflns_used    3719
_cell_measurement_temperature    150(2)
_cell_measurement_theta_max      79.8878
_cell_measurement_theta_min      6.1494
_cell_volume                     1414.7(2)
_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 Rev1143 (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 0.970
_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  0.0372
_diffrn_reflns_av_unetI/netI     0.0376
_diffrn_reflns_Laue_measured_fraction_full 0.993
_diffrn_reflns_Laue_measured_fraction_max 0.970
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            5056
_diffrn_reflns_point_group_measured_fraction_full 0.993
_diffrn_reflns_point_group_measured_fraction_max 0.970
_diffrn_reflns_theta_full        67.679
_diffrn_reflns_theta_max         79.922
_diffrn_reflns_theta_min         6.147
_diffrn_source                   'I-mu-S microsource X-ray tube'
_diffrn_source_current           '1.0 mA'
_diffrn_source_voltage           '50 kV'
_exptl_absorpt_coefficient_mu    1.382
_exptl_absorpt_correction_T_max  0.7543
_exptl_absorpt_correction_T_min  0.6126
_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    1.757
_exptl_crystal_description       plate
_exptl_crystal_F_000             768
_exptl_crystal_size_max          0.160
_exptl_crystal_size_mid          0.150
_exptl_crystal_size_min          0.020
_refine_diff_density_max         0.321
_refine_diff_density_min         -0.249
_refine_diff_density_rms         0.063
_refine_ls_extinction_coef       0.0052(11)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2018/3 (Sheldrick 2018)'
_refine_ls_goodness_of_fit_ref   1.160
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     72
_refine_ls_number_reflns         812
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.160
_refine_ls_R_factor_all          0.0483
_refine_ls_R_factor_gt           0.0461
_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)+(0.0842P)²+0.8362P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1406
_refine_ls_wR_factor_ref         0.1427
_reflns_Friedel_coverage         0.000
_reflns_number_gt                741
_reflns_number_total             812
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d1ra00953b2.cif
_cod_data_source_block           L2DW22G_0m
_cod_original_sg_symbol_Hall     '-C 2bc 2'
_cod_original_sg_symbol_H-M      'C m c a'
_cod_database_code               7242871
_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   0.809
_shelx_estimated_absorpt_t_max   0.973
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y+1/2, z+1/2'
'-x, y+1/2, -z+1/2'
'x, -y, -z'
'x+1/2, y+1/2, z'
'-x+1/2, -y+1, z+1/2'
'-x+1/2, y+1, -z+1/2'
'x+1/2, -y+1/2, -z'
'-x, -y, -z'
'x, y-1/2, -z-1/2'
'x, -y-1/2, z-1/2'
'-x, y, z'
'-x+1/2, -y+1/2, -z'
'x+1/2, y, -z-1/2'
'x+1/2, -y, 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
C1 C 0.000000 0.29744(15) -0.18427(17) 0.0272(6) Uani 1 2 d S T P . .
H1 H 0.000000 0.232183 -0.173226 0.033 Uiso 1 2 calc R U P . .
C2 C 0.000000 0.34319(15) -0.27768(18) 0.0276(6) Uani 1 2 d S T P . .
H2 H 0.000000 0.316490 -0.345758 0.033 Uiso 1 2 calc R U P . .
C3 C 0.000000 0.51297(16) -0.32694(19) 0.0355(6) Uani 1 2 d S T P . .
H3A H 0.052097 0.493417 -0.393446 0.053 Uiso 0.5 1 calc R U P . .
H3B H 0.067562 0.564336 -0.297327 0.053 Uiso 0.5 1 calc R U P . .
H3C H -0.119658 0.533459 -0.339175 0.053 Uiso 0.5 1 calc R U P . .
C4 C 0.000000 0.35438(15) -0.00123(18) 0.0254(5) Uani 1 2 d S T P . .
N1 N 0.000000 0.36491(13) -0.11074(14) 0.0251(5) Uani 1 2 d S T P . .
N2 N 0.000000 0.45010(13) -0.15185(15) 0.0296(5) Uani 1 2 d S T P . .
N3 N 0.000000 0.43452(13) -0.25325(14) 0.0254(5) Uani 1 2 d S T P . .
N4 N 0.15958(18) 0.35084(9) 0.04807(11) 0.0262(4) Uani 1 1 d . . . . .
O1 O 0.29081(16) 0.35979(9) -0.00925(10) 0.0352(4) Uani 1 1 d . . . . .
O2 O 0.17141(17) 0.33925(8) 0.14400(9) 0.0313(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 0.0181 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
N1 C1 C2 105.07(19) . . ?
N1 C1 H1 127.5 . . ?
C2 C1 H1 127.5 . . ?
N3 C2 C1 105.60(19) . . ?
N3 C2 H2 127.2 . . ?
C1 C2 H2 127.2 . . ?
N3 C3 H3A 109.5 . . ?
N3 C3 H3B 109.5 . . ?
H3A C3 H3B 109.5 . . ?
N3 C3 H3C 109.5 . . ?
H3A C3 H3C 109.5 . . ?
H3B C3 H3C 109.5 . . ?
N3 C3 H3A 109.5(4) . 12 ?
H3A C3 H3A 48.3 . 12 ?
H3B C3 H3A 140.2 . 12 ?
H3C C3 H3A 64.1 . 12 ?
N3 C3 H3B 109.5(4) . 12 ?
H3A C3 H3B 140.2 . 12 ?
H3B C3 H3B 64.1 . 12 ?
H3C C3 H3B 48.3 . 12 ?
H3A C3 H3B 109.5 12 12 ?
N3 C3 H3C 109.47(7) . 12 ?
H3A C3 H3C 64.1 . 12 ?
H3B C3 H3C 48.3 . 12 ?
H3C C3 H3C 140.2 . 12 ?
H3A C3 H3C 109.5 12 12 ?
H3B C3 H3C 109.5 12 12 ?
N4 C4 N4 125.6(2) 12 . ?
N4 C4 N1 117.18(10) 12 . ?
N4 C4 N1 117.18(10) . . ?
N2 N1 C1 112.84(18) . . ?
N2 N1 C4 119.34(17) . . ?
C1 N1 C4 127.82(19) . . ?
N3 N2 N1 103.32(16) . . ?
N2 N3 C2 113.17(18) . . ?
N2 N3 C3 119.94(18) . . ?
C2 N3 C3 126.89(19) . . ?
O2 N4 O1 122.06(14) . . ?
O2 N4 C4 121.36(14) . . ?
O1 N4 C4 116.58(14) . . ?
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
C1 N1 1.351(3) . ?
C1 C2 1.362(3) . ?
C1 H1 0.9500 . ?
C2 N3 1.351(3) . ?
C2 H2 0.9500 . ?
C3 N3 1.470(3) . ?
C3 H3A 0.9800 . ?
C3 H3B 0.9800 . ?
C3 H3C 0.9800 . ?
C3 H3A 0.980(16) 12 ?
C3 H3B 0.98(2) 12 ?
C3 H3C 0.980(3) 12 ?
C4 N4 1.3814(17) 12 ?
C4 N4 1.3814(17) . ?
C4 N1 1.406(3) . ?
N1 N2 1.334(2) . ?
N2 N3 1.313(3) . ?
N4 O2 1.2387(18) . ?
N4 O1 1.2541(18) . ?
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
N1 C1 C2 N3 0.000(0) . . . . ?
C2 C1 N1 N2 0.000(0) . . . . ?
C2 C1 N1 C4 180.000(0) . . . . ?
N4 C4 N1 N2 89.20(16) 12 . . . ?
N4 C4 N1 N2 -89.20(16) . . . . ?
N4 C4 N1 C1 -90.80(16) 12 . . . ?
N4 C4 N1 C1 90.80(16) . . . . ?
C1 N1 N2 N3 0.000(0) . . . . ?
C4 N1 N2 N3 180.000(0) . . . . ?
N1 N2 N3 C2 0.000(0) . . . . ?
N1 N2 N3 C3 180.000(0) . . . . ?
C1 C2 N3 N2 0.000(0) . . . . ?
C1 C2 N3 C3 180.000(0) . . . . ?
N4 C4 N4 O2 3.7(3) 12 . . . ?
N1 C4 N4 O2 -178.09(15) . . . . ?
N4 C4 N4 O1 -176.46(14) 12 . . . ?
N1 C4 N4 O1 1.8(2) . . . . ?
