#------------------------------------------------------------------------------
#$Date: 2019-11-08 03:09:27 +0200 (Fri, 08 Nov 2019) $
#$Revision: 224986 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/05/87/7058778.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_7058778
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 N4 O4'
_chemical_formula_weight         200.12
_space_group_crystal_system      orthorhombic
_space_group_IT_number           56
_space_group_name_Hall           '-P 2ab 2ac'
_space_group_name_H-M_alt        'P c c n'
_symmetry_space_group_name_Hall  '-P 2ab 2ac'
_symmetry_space_group_name_H-M   'P c c n'
_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                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   6.042(5)
_cell_length_b                   9.000(8)
_cell_length_c                   13.277(11)
_cell_measurement_reflns_used    2007
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      28.14
_cell_measurement_theta_min      3.07
_cell_volume                     722.0(11)
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_diffrn_ambient_temperature      100(2)
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measurement_device_type  'BRUKER SMART APEXII CCD'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0587
_diffrn_reflns_av_unetI/netI     0.0498
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            4448
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.996
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         28.269
_diffrn_reflns_theta_min         3.069
_exptl_absorpt_coefficient_mu    0.194
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.841
_exptl_crystal_description       block
_exptl_crystal_F_000             408
_exptl_crystal_size_max          0.400
_exptl_crystal_size_mid          0.360
_exptl_crystal_size_min          0.300
_refine_diff_density_max         0.349
_refine_diff_density_min         -0.318
_refine_diff_density_rms         0.065
_refine_ls_extinction_coef       0.038(5)
_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   1.061
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     62
_refine_ls_number_reflns         889
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.061
_refine_ls_R_factor_all          0.0406
_refine_ls_R_factor_gt           0.0361
_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)+(0.0318P)²+0.3541P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0911
_refine_ls_wR_factor_ref         0.0948
_reflns_Friedel_coverage         0.000
_reflns_number_gt                794
_reflns_number_total             889
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            c9nj02569c2.cif
_cod_data_source_block           151120a_0m
_cod_depositor_comments
'Adding full bibliography for 7058774--7058778.cif.'
_cod_original_cell_volume        721.9(10)
_cod_database_code               7058778
_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   0.927
_shelx_estimated_absorpt_t_max   0.944
_shelx_res_file
;

TITL 151120a_0m in Pccn
    151120a_0m.res
    created by SHELXL-2018/3 at 17:31:11 on 15-Aug-2019
CELL 0.71073   6.04150   9.00000  13.27690  90.0000  90.0000  90.0000
ZERR    4.00   0.00500   0.00760   0.01070   0.0000   0.0000   0.0000
LATT 1
SYMM 0.5-X, 0.5-Y, Z
SYMM -X, 0.5+Y, 0.5-Z
SYMM 0.5+X, -Y, 0.5-Z
SFAC C  H  N  O  F
UNIT 12  24  16  16  8
LIST 6 ! automatically inserted. Change 6 to 4 for CHECKCIF!!
L.S. 5
ACTA
BOND $H
FMAP 2
PLAN 5
SIZE 0.40 0.36 0.30
TEMP -173.000
WGHT    0.031800    0.354100
EXTI    0.038290
FVAR       0.22258
MOLE 2
C1    1    0.250000    0.750000   -0.017356    10.50000    0.01615    0.05098 =
         0.01372    0.00000    0.00000    0.00019
C2    1    0.070786    0.736643    0.063318    11.00000    0.01579    0.02983 =
         0.01586    0.00173    0.00077    0.00165
AFIX  23
H2A   2   -0.036287    0.819913    0.063409    11.00000   -1.20000
H2B   2   -0.006470    0.639636    0.063409    11.00000   -1.20000
AFIX   0
F1    5    0.229052    0.870134   -0.078441    11.00000    0.02478    0.10412 =
         0.03413    0.04163   -0.00213   -0.00344
N1    3    0.250000    0.750000    0.143299    10.50000    0.02269    0.01776 =
         0.01355    0.00000    0.00000    0.00058
AFIX  23
H1A   2    0.263674    0.667331    0.182269    10.50000   -1.20000
H1B   2    0.236327    0.832668    0.182270    10.50000   -1.20000
AFIX   0
MOLE 1
N2    3    0.210501    0.124511    0.189963    11.00000    0.01384    0.01698 =
         0.01775    0.00071   -0.00035    0.00152
N3    3    0.250000    0.250000    0.246666    10.50000    0.02785    0.01669 =
         0.01532    0.00000    0.00000   -0.00063
O1    4    0.272945    0.106076    0.102680    11.00000    0.02515    0.02374 =
         0.01725   -0.00368    0.00387    0.00136
O2    4    0.118223    0.023774    0.239776    11.00000    0.02525    0.01921 =
         0.02593    0.00377    0.00501   -0.00318
HKLF 4




REM  151120a_0m in Pccn
REM wR2 = 0.094813, GooF = S = 1.06069, Restrained GooF = 1.06069 for all data
REM R1 = 0.036052 for 794 Fo > 4sig(Fo) and 0.040561 for all 889 data
REM 62 parameters refined using 0 restraints

END

WGHT      0.0301      0.3927

REM Highest difference peak  0.349,  deepest hole -0.318,  1-sigma level  0.065
Q1    1   0.1533  0.7439  0.0154  11.00000  0.05    0.35
Q2    1   0.2474  0.8994 -0.0642  11.00000  0.05    0.26
Q3    1   0.1556  0.7423  0.1058  11.00000  0.05    0.24
Q4    1   0.2197  0.8236 -0.1166  11.00000  0.05    0.19
Q5    1   0.2337  0.0263  0.0802  11.00000  0.05    0.19
;
_shelx_res_checksum              13094
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, -y+1/2, z'
'-x, y+1/2, -z+1/2'
'x+1/2, -y, -z+1/2'
'-x, -y, -z'
'x-1/2, y-1/2, -z'
'x, -y-1/2, z-1/2'
'-x-1/2, y, 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
_atom_site_refinement_flags_occupancy
C1 C 0.250000 0.750000 -0.01736(14) 0.0270(5) Uani 1 2 d S T P
C2 C 0.0708(2) 0.73664(15) 0.06332(9) 0.0205(3) Uani 1 1 d . . .
H2A H -0.036287 0.819913 0.063409 0.025 Uiso 1 1 calc R U .
H2B H -0.006470 0.639636 0.063409 0.025 Uiso 1 1 calc R U .
F1 F 0.22905(15) 0.87013(16) -0.07844(7) 0.0543(4) Uani 1 1 d . . .
N1 N 0.250000 0.750000 0.14330(11) 0.0180(3) Uani 1 2 d S T P
H1A H 0.263674 0.667331 0.182269 0.022 Uiso 0.5 1 calc R U P
H1B H 0.236327 0.832668 0.182270 0.022 Uiso 0.5 1 calc R U P
N2 N 0.21050(16) 0.12451(11) 0.18996(8) 0.0162(3) Uani 1 1 d . . .
N3 N 0.250000 0.250000 0.24667(11) 0.0200(4) Uani 1 2 d S T P
O1 O 0.27294(16) 0.10608(11) 0.10268(6) 0.0220(3) Uani 1 1 d . . .
O2 O 0.11822(16) 0.02377(10) 0.23978(7) 0.0235(3) Uani 1 1 d . . .
loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
C1 0.0161(8) 0.0510(13) 0.0137(8) 0.000 0.000 0.0002(8)
C2 0.0158(6) 0.0298(7) 0.0159(6) 0.0017(5) 0.0008(4) 0.0016(5)
F1 0.0248(5) 0.1041(10) 0.0341(5) 0.0416(6) -0.0021(4) -0.0034(5)
N1 0.0227(8) 0.0178(7) 0.0136(7) 0.000 0.000 0.0006(5)
N2 0.0138(5) 0.0170(5) 0.0177(5) 0.0007(4) -0.0004(4) 0.0015(4)
N3 0.0278(8) 0.0167(7) 0.0153(7) 0.000 0.000 -0.0006(6)
O1 0.0251(5) 0.0237(5) 0.0172(5) -0.0037(3) 0.0039(3) 0.0014(4)
O2 0.0253(5) 0.0192(5) 0.0259(5) 0.0038(4) 0.0050(4) -0.0032(4)
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
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
F1 C1 F1 106.63(18) 2_565 .
F1 C1 C2 114.55(8) 2_565 2_565
F1 C1 C2 114.98(8) . 2_565
F1 C1 C2 114.98(8) 2_565 .
F1 C1 C2 114.55(7) . .
C2 C1 C2 90.97(15) 2_565 .
N1 C2 C1 88.78(11) . .
N1 C2 H2A 113.9 . .
C1 C2 H2A 113.9 . .
N1 C2 H2B 113.9 . .
C1 C2 H2B 113.9 . .
H2A C2 H2B 111.1 . .
C2 N1 C2 91.46(13) . 2_565
C2 N1 H1A 113.4 . .
C2 N1 H1A 113.4 2_565 .
C2 N1 H1B 113.4 . .
C2 N1 H1B 113.4 2_565 .
H1A N1 H1B 110.7 . .
O1 N2 O2 122.42(11) . .
O1 N2 N3 124.90(11) . .
O2 N2 N3 112.44(11) . .
N2 N3 N2 113.78(15) 2 .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
C1 F1 1.3575(17) 2_565
C1 F1 1.3575(17) .
C1 C2 1.5277(19) 2_565
C1 C2 1.5277(19) .
C2 N1 1.5213(17) .
C2 H2A 0.9900 .
C2 H2B 0.9900 .
N1 H1A 0.9100 .
N1 H1B 0.9100 .
N2 O1 1.2299(16) .
N2 O2 1.2531(15) .
N2 N3 1.3781(15) .
