#------------------------------------------------------------------------------
#$Date: 2025-08-19 00:06:14 +0300 (Tue, 19 Aug 2025) $
#$Revision: 301780 $
#$URL: file:///home/coder/svn-repositories/cod/cif/1/55/45/1554530.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_1554530
loop_
_publ_author_name
'Palysaeva, Nadezhda V.'
'Gladyshkin, Aleksei G.'
'Vatsadze, Irina A.'
'Suponitsky, Kyrill Yu.'
'Dmitriev, Dmitry E.'
'Sheremetev, Aleksei B.'
_publ_section_title
;
 N-(2-Fluoro-2,2-dinitroethyl)azoles: a novel assembly of diverse
 explosophoric building blocks for energetic compound design
;
_journal_issue                   2
_journal_name_full               'Organic Chemistry Frontiers'
_journal_page_first              249
_journal_paper_doi               10.1039/C8QO01173G
_journal_volume                  6
_journal_year                    2019
_chemical_formula_moiety         'C3 H3 F N6 O4'
_chemical_formula_sum            'C3 H3 F N6 O4'
_chemical_formula_weight         206.11
_space_group_crystal_system      orthorhombic
_space_group_IT_number           33
_space_group_name_Hall           'P 2c -2n'
_space_group_name_H-M_alt        'P n a 21'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-2014/6
_audit_update_record
;
2018-10-20 deposited with the CCDC.
2018-12-03 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   11.4331(11)
_cell_length_b                   5.7212(6)
_cell_length_c                   11.2434(11)
_cell_measurement_reflns_used    2339
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      27.81
_cell_measurement_theta_min      3.56
_cell_volume                     735.44(13)
_computing_cell_refinement       'SAINT (Bruker, 2013)'
_computing_data_collection       'APEX (Bruker, 2013)'
_computing_data_reduction        'SAINT (Bruker, 2013)'
_computing_molecular_graphics    'SHELXL-2014/6 (Sheldrick, 2014)'
_computing_publication_material
'SHELXL-2014/6 (Sheldrick, 2014) and PLATON (Spek, 2009)'
_computing_structure_refinement  'SHELXL-2014/6 (Sheldrick, 2014)'
_computing_structure_solution    'SHELXL-2014/6 (Sheldrick, 2014)'
_diffrn_ambient_temperature      100(2)
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0335
_diffrn_reflns_av_unetI/netI     0.0290
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            7221
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.996
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         28.920
_diffrn_reflns_theta_min         3.564
_diffrn_source                   'sealed tube'
_exptl_absorpt_coefficient_mu    0.182
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.862
_exptl_crystal_description       prizm
_exptl_crystal_F_000             416
_exptl_crystal_size_max          0.32
_exptl_crystal_size_mid          0.24
_exptl_crystal_size_min          0.20
_refine_diff_density_max         0.202
_refine_diff_density_min         -0.241
_refine_diff_density_rms         0.047
_refine_ls_abs_structure_details
;
 Flack x determined using 780 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.0(5)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.045
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     127
_refine_ls_number_reflns         1930
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.045
_refine_ls_R_factor_all          0.0330
_refine_ls_R_factor_gt           0.0289
_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)+(0.0343P)²+0.0120P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0628
_refine_ls_wR_factor_ref         0.0648
_reflns_Friedel_coverage         0.903
_reflns_Friedel_fraction_full    0.998
_reflns_Friedel_fraction_max     0.993
_reflns_number_gt                1773
_reflns_number_total             1930
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            c8qo01173g2.cif
_cod_data_source_block           comp28
_cod_database_code               1554530
_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.
;
_shelxl_version_number           2014/6
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, z+1/2'
'x+1/2, -y+1/2, z'
'-x+1/2, 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
_atom_site_refinement_flags_adp
F1 F 0.01885(10) 0.2493(2) 0.98105(12) 0.0181(3) Uani 1 1 d . .
O1 O 0.06999(16) 0.3699(3) 1.19109(15) 0.0286(4) Uani 1 1 d . .
O2 O -0.02123(14) 0.0717(3) 1.26724(15) 0.0258(4) Uani 1 1 d . .
O3 O -0.06505(14) -0.2801(3) 1.03529(15) 0.0239(4) Uani 1 1 d . .
O4 O 0.11405(13) -0.1500(3) 1.04911(16) 0.0255(4) Uani 1 1 d . .
N1 N -0.21097(14) 0.1275(3) 0.93820(14) 0.0116(3) Uani 1 1 d . .
N2 N -0.22441(15) 0.3243(3) 0.87158(16) 0.0157(4) Uani 1 1 d . .
N3 N -0.26402(14) 0.2559(3) 0.77049(17) 0.0176(4) Uani 1 1 d . .
N4 N -0.27780(14) 0.0184(3) 0.76753(16) 0.0178(4) Uani 1 1 d . .
N5 N 0.00979(15) 0.1970(3) 1.18567(16) 0.0162(4) Uani 1 1 d . .
N6 N 0.00783(15) -0.1278(3) 1.04816(16) 0.0164(4) Uani 1 1 d . .
C1 C -0.24381(17) -0.0560(4) 0.87249(18) 0.0152(4) Uani 1 1 d . .
H1 H -0.2427 -0.2145 0.8977 0.018 Uiso 1 1 calc R U
C2 C -0.16816(16) 0.1451(3) 1.05957(17) 0.0124(4) Uani 1 1 d . .
H2A H -0.2033 0.0195 1.1085 0.015 Uiso 1 1 calc R U
H2B H -0.1919 0.2973 1.0939 0.015 Uiso 1 1 calc R U
C3 C -0.03596(16) 0.1241(3) 1.06266(18) 0.0129(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 0.0033 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'
F F 0.0171 0.0103 '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
C1 N1 N2 108.28(16)
C1 N1 C2 131.89(17)
N2 N1 C2 119.83(16)
N3 N2 N1 105.96(17)
N2 N3 N4 111.37(18)
C1 N4 N3 105.43(18)
O1 N5 O2 127.67(19)
O1 N5 C3 117.55(17)
O2 N5 C3 114.77(16)
O3 N6 O4 127.51(18)
O3 N6 C3 117.57(16)
O4 N6 C3 114.91(16)
N4 C1 N1 108.97(19)
N4 C1 H1 125.5
N1 C1 H1 125.5
N1 C2 C3 110.58(15)
N1 C2 H2A 109.5
C3 C2 H2A 109.5
N1 C2 H2B 109.5
C3 C2 H2B 109.5
H2A C2 H2B 108.1
F1 C3 C2 114.43(16)
F1 C3 N6 106.29(15)
C2 C3 N6 113.42(15)
F1 C3 N5 108.42(15)
C2 C3 N5 109.77(15)
N6 C3 N5 103.87(14)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
F1 C3 1.322(2)
O1 N5 1.206(2)
O2 N5 1.217(3)
O3 N6 1.214(2)
O4 N6 1.221(2)
N1 C1 1.337(3)
N1 N2 1.361(2)
N1 C2 1.453(2)
N2 N3 1.285(3)
N3 N4 1.368(3)
N4 C1 1.313(3)
N5 C3 1.536(3)
N6 C3 1.534(3)
C1 H1 0.9500
C2 C3 1.517(2)
C2 H2A 0.9900
C2 H2B 0.9900
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
C1 N1 N2 N3 0.1(2)
C2 N1 N2 N3 -179.33(16)
N1 N2 N3 N4 0.1(2)
N2 N3 N4 C1 -0.3(2)
N3 N4 C1 N1 0.4(2)
N2 N1 C1 N4 -0.3(2)
C2 N1 C1 N4 179.03(18)
C1 N1 C2 C3 89.6(2)
N2 N1 C2 C3 -91.1(2)
N1 C2 C3 F1 45.3(2)
N1 C2 C3 N6 -76.9(2)
N1 C2 C3 N5 167.42(15)
O3 N6 C3 F1 -126.12(19)
O4 N6 C3 F1 52.7(2)
O3 N6 C3 C2 0.5(2)
O4 N6 C3 C2 179.31(17)
O3 N6 C3 N5 119.59(19)
O4 N6 C3 N5 -61.6(2)
O1 N5 C3 F1 11.0(2)
O2 N5 C3 F1 -169.86(17)
O1 N5 C3 C2 -114.7(2)
O2 N5 C3 C2 64.5(2)
O1 N5 C3 N6 123.74(19)
O2 N5 C3 N6 -57.1(2)
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 PubChem 168304521
