#------------------------------------------------------------------------------
#$Date: 2025-08-21 23:04:39 +0300 (Thu, 21 Aug 2025) $
#$Revision: 301851 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/05/87/7058775.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_7058775
loop_
_publ_author_name
'Chen, Jifeng'
'Yu, Yi'
'Zhang, Shujuan'
'Li, Yuchuan'
'Pang, Siping'
_publ_section_title
;
 Energetic materials with fluorinated four-membered heterocyclic ring:
 3,3′-difluoroazetidine (DFAZ) salts
;
_journal_issue                   38
_journal_name_full               'New Journal of Chemistry'
_journal_page_first              15115
_journal_paper_doi               10.1039/C9NJ02569C
_journal_volume                  43
_journal_year                    2019
_chemical_formula_sum            'C3 H6 Cl F2 N O4'
_chemical_formula_weight         193.54
_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_space_group_name_Hall  '-P 2ac 2n'
_symmetry_space_group_name_H-M   'P n m a'
_atom_sites_solution_hydrogens   mixed
_audit_creation_method           SHELXL-2018/3
_audit_update_record
;
2019-08-22 deposited with the CCDC.    2019-08-26 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   12.1852(8)
_cell_length_b                   7.0366(3)
_cell_length_c                   7.5024(5)
_cell_measurement_reflns_used    864
_cell_measurement_temperature    101(2)
_cell_measurement_theta_max      29.4324
_cell_measurement_theta_min      3.1820
_cell_volume                     643.27(7)
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_diffrn_ambient_temperature      101(2)
_diffrn_measured_fraction_theta_full 0.995
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measurement_device_type  'Xcalibur, Eos, Gemini'
_diffrn_measurement_method       'ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0305
_diffrn_reflns_av_unetI/netI     0.0261
_diffrn_reflns_Laue_measured_fraction_full 0.995
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       9
_diffrn_reflns_limit_l_min       -9
_diffrn_reflns_number            2483
_diffrn_reflns_point_group_measured_fraction_full 0.995
_diffrn_reflns_point_group_measured_fraction_max 0.996
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         25.992
_diffrn_reflns_theta_min         3.189
_exptl_absorpt_coefficient_mu    0.602
_exptl_crystal_colour            white
_exptl_crystal_density_diffrn    1.998
_exptl_crystal_description       block
_exptl_crystal_F_000             392
_refine_diff_density_max         0.658
_refine_diff_density_min         -0.992
_refine_diff_density_rms         0.155
_refine_ls_extinction_coef       0.011(2)
_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   1.147
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     74
_refine_ls_number_reflns         687
_refine_ls_number_restraints     60
_refine_ls_restrained_S_all      1.100
_refine_ls_R_factor_all          0.0813
_refine_ls_R_factor_gt           0.0781
_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)+(0.0200P)²+13.3715P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1893
_refine_ls_wR_factor_ref         0.1904
_reflns_Friedel_coverage         0.000
_reflns_number_gt                635
_reflns_number_total             687
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            c9nj02569c2.cif
_cod_data_source_block           exp_3232
_cod_depositor_comments
'Adding full bibliography for 7058774--7058778.cif.'
_cod_database_code               7058775
_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.
;
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'x+1/2, -y+1/2, -z+1/2'
'-x, y+1/2, -z'
'-x, -y, -z'
'x-1/2, y, -z-1/2'
'-x-1/2, y-1/2, z-1/2'
'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
F1 F 0.4174(4) 0.250000 -0.6300(8) 0.0242(15) Uani 1 2 d S T P . .
F2 F 0.4526(5) 0.250000 -0.9158(8) 0.0261(15) Uani 1 2 d S T P . .
N1 N 0.6733(6) 0.250000 -0.7310(11) 0.025(2) Uani 1 2 d S T P . .
H1C H 0.715522 0.250000 -0.830854 0.030 Uiso 1 2 d R U P . .
H1D H 0.715680 0.250000 -0.631302 0.030 Uiso 1 2 d R U P . .
C1 C 0.5863(5) 0.0966(9) -0.7302(9) 0.0187(15) Uani 1 1 d . . . . .
H1A H 0.581168 0.026303 -0.616166 0.022 Uiso 1 1 calc R U . . .
H1B H 0.591077 0.008153 -0.832509 0.022 Uiso 1 1 calc R U . . .
C2 C 0.5000(7) 0.250000 -0.7519(12) 0.0132(18) Uani 1 2 d S T P . .
Cl1 Cl 0.67736(17) 0.250000 -0.2333(3) 0.0113(6) Uani 1 2 d S TU P . .
O3 O 0.7591(5) 0.250000 -0.3742(8) 0.0178(15) Uani 1 2 d S TU P A .
O1 O 0.5710(6) 0.2103(12) -0.3086(11) 0.016(3) Uani 0.5 1 d . U P A -1
O2 O 0.6785(10) 0.4336(18) -0.1521(17) 0.019(3) Uani 0.5 1 d . U P A -1
O4 O 0.7045(10) 0.1131(19) -0.0988(15) 0.018(3) Uani 0.5 1 d . U P A -1
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'
Cl Cl 0.1484 0.1585 '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'
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
C1 N1 C1 91.1(6) . 8_565
C1 N1 H1C 113.6 . .
C1 N1 H1C 113.6 8_565 .
C1 N1 H1D 113.3 . .
C1 N1 H1D 113.3 8_565 .
H1C N1 H1D 110.9 . .
N1 C1 C2 88.7(5) . .
N1 C1 H1A 113.9 . .
C2 C1 H1A 113.9 . .
N1 C1 H1B 113.9 . .
C2 C1 H1B 113.9 . .
H1A C1 H1B 111.1 . .
F2 C2 F1 107.1(7) . .
F2 C2 C1 113.1(5) . 8_565
F1 C2 C1 116.2(5) . 8_565
F2 C2 C1 113.1(5) . .
F1 C2 C1 116.2(5) . .
C1 C2 C1 90.8(7) 8_565 .
O2 Cl1 O4 107.8(8) . .
O2 Cl1 O1 110.6(6) . .
O4 Cl1 O1 110.7(6) . .
O2 Cl1 O3 107.7(5) . .
O4 Cl1 O3 110.7(5) . .
O1 Cl1 O3 109.4(4) . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
F1 C2 1.360(10) .
F2 C2 1.359(11) .
N1 C1 1.513(8) .
N1 C1 1.513(8) 8_565
N1 H1C 0.9090 .
N1 H1D 0.9089 .
C1 C2 1.516(8) .
C1 H1A 0.9900 .
C1 H1B 0.9900 .
Cl1 O2 1.429(12) .
Cl1 O4 1.433(13) .
Cl1 O1 1.441(8) .
Cl1 O3 1.453(6) .
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_4
C1 N1 C1 C2 6.4(7) 8_565 .
N1 C1 C2 F2 109.2(6) . .
N1 C1 C2 F1 -126.3(6) . .
N1 C1 C2 C1 -6.4(7) . 8_565
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 PubChem 168349448
