#------------------------------------------------------------------------------
#$Date: 2025-08-19 00:52:38 +0200 (Tue 19 de Aug de 2025) $
#$Revision: 301791 $
#$URL: svn://www.crystallography.net/cod/cif/2/00/97/2009713.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/. The original data for this entry
# were provided by IUCr Journals, http://journals.iucr.org/.
#
# The file may be used within the scientific community so long as
# proper attribution is given to the journal article from which the
# data were obtained.
#
data_2009713
loop_
_publ_author_name
'Abdul-Ghani, M.'
'Pritchard, R.G.'
'Tipping, A.E.'
_publ_section_title
;
 (<i>Z</i>,<i>Z</i>)-5-Chloro-1,1,1,6,6,6-hexafluoro-3,4-diaza-4-hexen-2-one
 oxime, formed by the action of hydroxylamine on
 2,5-dichlorohexafluoro-3,4-diazahexa-2,4-diene
;
_journal_issue                   5
_journal_name_full               'Acta Crystallographica Section C'
_journal_page_first              721
_journal_page_last               722
_journal_paper_doi               10.1107/S0108270193012326
_journal_volume                  50
_journal_year                    1994
_chemical_formula_moiety         'C4 H2 Cl F6 N3 O'
_chemical_formula_sum            'C4 H2 Cl F6 N3 O'
_chemical_formula_weight         257.52
_chemical_melting_point          392.0(10)
_chemical_name_systematic
;
(ZZ)-2-Chloro-1,1,1,6,6,6-hexafluoro-3,4-diazahex-2-en-5-one oxime
;
_space_group_IT_number           2
_symmetry_cell_setting           triclinic
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_cell_angle_alpha                75.08(3)
_cell_angle_beta                 81.69(4)
_cell_angle_gamma                83.08(4)
_cell_formula_units_Z            2
_cell_length_a                   5.141(3)
_cell_length_b                   6.916(2)
_cell_length_c                   13.250(5)
_cell_measurement_reflns_used    25
_cell_measurement_temperature    296
_cell_measurement_theta_max      8.5
_cell_measurement_theta_min      6.4
_cell_volume                     448.7(3)
_computing_cell_refinement
'CAD-4 Diffractometer Control (Enraf-Nonius,1989)'
_computing_data_collection
'CAD-4 Diffractometer Control (Enraf-Nonius,1989)'
_computing_data_reduction        'TEXSAN: PROCESS (MSC, 1985)'
_computing_molecular_graphics    'PLUTO (Motherwell and Clegg, 1978)'
_computing_publication_material  'TEXSAN: FINISH (MSC, 1985)'
_computing_structure_refinement  'TEXSAN: LS (MSC, 1985)'
_computing_structure_solution    'SHELXS86 (Sheldrick, 1985)'
_diffrn_ambient_temperature      296
_diffrn_measurement_device       CAD-4
_diffrn_measurement_method       'omega/2-theta scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'X-ray tube'
_diffrn_radiation_type           MoKalpha
_diffrn_radiation_wavelength     0.71069
_diffrn_reflns_av_R_equivalents  0.0473
_diffrn_reflns_limit_h_max       5
_diffrn_reflns_limit_h_min       0
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            1610
_diffrn_reflns_theta_max         24.99
_diffrn_reflns_theta_min         2
_diffrn_standards_decay_%        0.00
_diffrn_standards_interval_time  ' 180 '
_diffrn_standards_number         3
_exptl_absorpt_coefficient_mu    0.4967
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.906
_exptl_crystal_description       prism
_exptl_crystal_F_000             252.00
_exptl_crystal_size_max          0.30
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.20
_refine_diff_density_max         -0.24371
_refine_diff_density_min         0.26512
_refine_ls_goodness_of_fit_obs   2.402
_refine_ls_hydrogen_treatment    refall
_refine_ls_matrix_type           full
_refine_ls_number_parameters     144
_refine_ls_number_reflns         810
_refine_ls_number_restraints     0
_refine_ls_R_factor_obs          0.0540
_refine_ls_shift/esd_max         0.0021
_refine_ls_structure_factor_coef F
_refine_ls_weighting_scheme      sigma
_refine_ls_wR_factor_obs         0.0580
_reflns_number_observed          810
_reflns_number_total             1545
_reflns_observed_criterion       3sigmaI
_cod_data_source_file            hu1073.cif
_cod_data_source_block           U166
_cod_depositor_comments
;
The following automatic conversions were performed:

'_chemical_melting_point' value '391-393 K' was changed to
'392.0(10)' - the average value was taken and precision was
estimated.

Automatic conversion script
Id: cif_fix_values 1646 2011-03-28 12:23:43Z adriana 

The following automatic conversions were performed:

'_chemical_melting_point' value '391-393 K' was changed to
'392.0(10)' - the average value was taken and precision was
estimated.

Automatic conversion script
Id: cif_fix_values 1715 2011-07-08 13:25:40Z adriana 
;
_cod_original_cell_volume        448.8(7)
_cod_database_code               2009713
loop_
_symmetry_equiv_pos_as_xyz
x,y,z
-x,-y,-z
loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_12
_atom_site_aniso_U_13
_atom_site_aniso_U_23
Cl(1) 0.123(2) 0.0560(10) 0.117(2) 0.0156(9) -0.0490(10) -0.0216(9)
F(1) 0.188(5) 0.094(3) 0.130(4) -0.037(3) -0.100(3) -0.011(2)
F(2) 0.070(3) 0.190(5) 0.128(4) 0.011(3) -0.044(3) -0.042(3)
F(3) 0.132(4) 0.154(4) 0.062(3) -0.044(3) -0.016(2) -0.011(2)
F(4) 0.130(3) 0.046(2) 0.125(3) -0.005(2) -0.069(3) -0.010(2)
F(5) 0.114(3) 0.076(2) 0.091(3) 0.003(2) -0.012(2) -0.042(2)
F(6) 0.097(3) 0.069(2) 0.100(3) -0.035(2) -0.026(2) -0.017(2)
O(1) 0.108(4) 0.050(2) 0.097(3) -0.005(2) -0.055(3) -0.022(2)
N(3) 0.066(3) 0.058(3) 0.056(3) -0.008(2) -0.022(3) -0.013(2)
N(4) 0.089(4) 0.048(3) 0.071(3) 0.002(2) -0.044(3) -0.015(2)
N(6) 0.076(3) 0.039(2) 0.066(3) -0.009(2) -0.025(3) -0.014(2)
C(1) 0.065(5) 0.079(4) 0.065(5) -0.008(3) -0.023(4) 0.001(3)
C(2) 0.056(4) 0.061(3) 0.062(4) -0.004(3) -0.017(3) -0.012(3)
C(5) 0.059(4) 0.045(3) 0.052(3) -0.005(2) -0.015(3) -0.013(2)
C(6) 0.077(5) 0.055(3) 0.073(5) -0.012(3) -0.027(4) -0.017(3)
loop_
_atom_site_label
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
Cl(1) 0.2912(4) 0.9492(2) 0.6701(2) 0.0970
F(1) 0.1540(10) 0.4722(7) 0.5933(3) 0.1299
F(2) -0.0877(8) 0.7370(7) 0.5896(3) 0.1272
F(3) 0.2629(9) 0.7428(7) 0.4918(3) 0.1157
F(4) 0.8203(8) 0.1053(4) 0.9252(3) 0.0971
F(5) 0.7746(8) 0.2068(5) 0.7620(3) 0.0907
F(6) 0.4357(8) 0.1703(4) 0.8750(3) 0.0858
O(1) 0.8144(10) 0.6752(5) 0.9234(4) 0.0800
N(3) 0.4042(9) 0.5570(6) 0.7298(3) 0.0589
N(4) 0.5315(9) 0.5930(7) 0.8044(4) 0.0664
N(6) 0.8279(9) 0.4699(6) 0.9272(3) 0.0582
C(1) 0.1570(10) 0.6630(10) 0.5860(5) 0.0713
C(2) 0.2920(10) 0.7011(8) 0.6695(4) 0.0592
C(5) 0.6800(10) 0.4435(7) 0.8640(4) 0.0509
C(6) 0.6770(10) 0.2284(8) 0.8559(5) 0.0658
H(4) 0.560(10) 0.718(9) 0.811(4) 0.08(2)
H(1) 0.910(10) 0.659(8) 0.968(5) 0.07(2)
loop_
_atom_type_symbol
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C 0.002 0.002 'International Tables for X-ray crystallography, 1974'
H 0.000 0.000 'International Tables for X-ray crystallography, 1974'
O 0.008 0.006 'International Tables for X-ray crystallography, 1974'
F 0.014 0.010 'International Tables for X-ray crystallography, 1974'
N 0.004 0.003 'International Tables for X-ray crystallography, 1974'
Cl 0.132 0.159 'International Tables for X-ray crystallography, 1974'
loop_
_diffrn_standard_refln_index_h
_diffrn_standard_refln_index_k
_diffrn_standard_refln_index_l
1 0 -3
0 2 3
-1 0 2
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_publ_flag
N(6) O(1) H(1) 93(4) ?
N(4) N(3) C(2) 119.0(5) yes
N(3) N(4) C(5) 120.7(5) yes
N(3) N(4) H(4) 125(3) ?
C(5) N(4) H(4) 113(3) ?
O(1) N(6) C(5) 109.2(4) yes
F(1) C(1) F(2) 106.4(6) ?
F(1) C(1) F(3) 107.2(6) ?
F(1) C(1) C(2) 112.1(5) ?
F(2) C(1) F(3) 105.2(5) ?
F(2) C(1) C(2) 112.3(6) ?
F(3) C(1) C(2) 113.2(5) ?
Cl(1) C(2) N(3) 125.3(4) yes
Cl(1) C(2) C(1) 115.4(4) yes
N(3) C(2) C(1) 119.3(5) yes
N(4) C(5) N(6) 124.2(5) yes
N(4) C(5) C(6) 119.8(5) yes
N(6) C(5) C(6) 116.0(5) ?
F(4) C(6) F(5) 108.2(6) ?
F(4) C(6) F(6) 107.8(5) ?
F(4) C(6) C(5) 110.0(5) ?
F(5) C(6) F(6) 107.4(5) ?
F(5) C(6) C(5) 111.7(5) ?
F(6) C(6) C(5) 111.7(5) ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_site_symmetry_1
_geom_bond_site_symmetry_2
_geom_bond_distance
_geom_bond_publ_flag
Cl(1) C(2) . . 1.718(5) yes
F(1) C(1) . . 1.300(7) ?
F(2) C(1) . . 1.297(7) ?
F(3) C(1) . . 1.296(6) ?
F(4) C(6) . . 1.323(6) ?
F(5) C(6) . . 1.311(7) ?
F(6) C(6) . . 1.321(7) ?
O(1) N(6) . . 1.402(5) yes
O(1) H(1) . . 0.80(6) ?
N(3) N(4) . . 1.348(6) yes
N(3) C(2) . . 1.245(6) yes
N(4) C(5) . . 1.356(6) yes
N(4) H(4) . . 0.92(6) ?
N(6) C(5) . . 1.269(6) yes
C(1) C(2) . . 1.482(8) yes
C(5) C(6) . . 1.520(7) yes
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 PubChem 139057160
