#------------------------------------------------------------------------------
#$Date: 2025-08-21 23:04:39 +0300 (Thu, 21 Aug 2025) $
#$Revision: 301851 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/05/87/7058776.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_7058776
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 F2 N2 O3'
_chemical_formula_weight         156.10
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   geom
_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                91.249(13)
_cell_angle_beta                 106.658(14)
_cell_angle_gamma                92.337(12)
_cell_formula_units_Z            2
_cell_length_a                   5.5333(8)
_cell_length_b                   6.1726(9)
_cell_length_c                   9.2437(16)
_cell_measurement_reflns_used    707
_cell_measurement_temperature    101(2)
_cell_measurement_theta_max      29.3828
_cell_measurement_theta_min      3.2996
_cell_volume                     302.03(8)
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_diffrn_ambient_temperature      101(2)
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type  'Xcalibur, Eos, Gemini'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0180
_diffrn_reflns_av_unetI/netI     0.0399
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_number            1910
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         25.993
_diffrn_reflns_theta_min         3.305
_exptl_absorpt_coefficient_mu    0.184
_exptl_crystal_colour            white
_exptl_crystal_density_diffrn    1.716
_exptl_crystal_description       needle
_exptl_crystal_F_000             160
_exptl_crystal_size_max          0.340
_exptl_crystal_size_mid          0.300
_exptl_crystal_size_min          0.150
_refine_diff_density_max         0.322
_refine_diff_density_min         -0.320
_refine_diff_density_rms         0.077
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.123
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     91
_refine_ls_number_reflns         1184
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.123
_refine_ls_R_factor_all          0.0467
_refine_ls_R_factor_gt           0.0383
_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)+(0.0423P)²+0.0423P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0909
_refine_ls_wR_factor_ref         0.0985
_reflns_Friedel_coverage         0.000
_reflns_number_gt                999
_reflns_number_total             1184
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            c9nj02569c2.cif
_cod_data_source_block           exp_3231
_cod_depositor_comments
'Adding full bibliography for 7058774--7058778.cif.'
_cod_database_code               7058776
_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   0.940
_shelx_estimated_absorpt_t_max   0.973
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -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
F1 F 0.4130(2) 0.74495(18) 0.95768(13) 0.0260(3) Uani 1 1 d . .
O2 O 0.2357(2) 0.7547(2) 0.42008(15) 0.0200(3) Uani 1 1 d . .
O3 O 0.0949(2) 0.7070(2) 0.61362(14) 0.0158(3) Uani 1 1 d . .
N2 N 0.0530(3) 0.7524(2) 0.47605(17) 0.0136(4) Uani 1 1 d . .
F2 F 0.8215(2) 0.75028(18) 1.03488(13) 0.0281(3) Uani 1 1 d . .
O1 O -0.1619(2) 0.7939(2) 0.39950(15) 0.0199(3) Uani 1 1 d . .
N1 N 0.6463(3) 0.7341(2) 0.68301(17) 0.0162(4) Uani 1 1 d . .
H1A H 0.795215 0.734028 0.659571 0.019 Uiso 1 1 calc R U
H1B H 0.513490 0.729682 0.597683 0.019 Uiso 1 1 calc R U
C2 C 0.6224(3) 0.7436(3) 0.9083(2) 0.0163(4) Uani 1 1 d . .
C1 C 0.6230(3) 0.5632(3) 0.7942(2) 0.0160(4) Uani 1 1 d . .
H1C H 0.770729 0.471720 0.825209 0.019 Uiso 1 1 calc R U
H1D H 0.463459 0.473029 0.761691 0.019 Uiso 1 1 calc R U
C3 C 0.6367(4) 0.9141(3) 0.7948(2) 0.0171(4) Uani 1 1 d . .
H3A H 0.484062 0.999682 0.762698 0.021 Uiso 1 1 calc R U
H3B H 0.791769 1.010136 0.826237 0.021 Uiso 1 1 calc R U
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'
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
O1 N2 O2 121.31(15)
O1 N2 O3 120.50(14)
O2 N2 O3 118.19(15)
C3 N1 C1 91.16(13)
C3 N1 H1A 113.4
C1 N1 H1A 113.4
C3 N1 H1B 113.4
C1 N1 H1B 113.4
H1A N1 H1B 110.7
F2 C2 F1 105.60(14)
F2 C2 C3 114.86(16)
F1 C2 C3 115.24(15)
F2 C2 C1 114.85(15)
F1 C2 C1 115.40(16)
C3 C2 C1 90.94(14)
N1 C1 C2 88.88(13)
N1 C1 H1C 113.8
C2 C1 H1C 113.8
N1 C1 H1D 113.8
C2 C1 H1D 113.8
H1C C1 H1D 111.1
N1 C3 C2 88.96(13)
N1 C3 H3A 113.8
C2 C3 H3A 113.8
N1 C3 H3B 113.8
C2 C3 H3B 113.8
H3A C3 H3B 111.0
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
F1 C2 1.362(2)
O2 N2 1.2607(18)
O3 N2 1.2654(19)
N2 O1 1.2371(19)
F2 C2 1.357(2)
N1 C3 1.514(2)
N1 C1 1.516(2)
N1 H1A 0.9100
N1 H1B 0.9100
C2 C3 1.517(3)
C2 C1 1.518(3)
C1 H1C 0.9900
C1 H1D 0.9900
C3 H3A 0.9900
C3 H3B 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
C3 N1 C1 C2 -1.82(14)
F2 C2 C1 N1 -116.28(15)
F1 C2 C1 N1 120.50(16)
C3 C2 C1 N1 1.81(13)
C1 N1 C3 C2 1.82(14)
F2 C2 C3 N1 116.27(15)
F1 C2 C3 N1 -120.63(16)
C1 C2 C3 N1 -1.82(13)
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 PubChem 168349449
