#------------------------------------------------------------------------------
#$Date: 2018-09-26 05:28:29 +0300 (Wed, 26 Sep 2018) $
#$Revision: 211171 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/24/26/2242648.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_2242648
loop_
_publ_author_name
'Elkin, Igor'
'Maris, Thierry'
'Hildgen, Patrice'
'Barrett, Christopher J.'
_publ_section_title
;
 Crystal structures of the solvent-free and ethanol disolvate forms of
 4,4'-(diazenediyl)bis(2,3,5,6-tetrafluorobenzoic acid) exemplifying
 self-stabilized azobenzene cis-configurations
;
_journal_coeditor_code           WM5460
_journal_issue                   10
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              1486
_journal_page_last               1490
_journal_paper_doi               10.1107/S2056989018012781
_journal_volume                  74
_journal_year                    2018
_chemical_formula_iupac          'C14 H2 F8 N2 O4'
_chemical_formula_moiety         'C14 H2 F8 N2 O4'
_chemical_formula_sum            'C14 H2 F8 N2 O4'
_chemical_formula_weight         414.18
_chemical_name_systematic
;
cis-2,3,5,6,2',3',5',6'-Octafluoro-4,4'-azinodibenzoic acid
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           15
_space_group_name_Hall           '-C 2yc'
_space_group_name_H-M_alt        'C 1 2/c 1'
_symmetry_space_group_name_Hall  '-C 2yc'
_symmetry_space_group_name_H-M   'C 1 2/c 1'
_atom_sites_solution_hydrogens   difmap
_atom_sites_solution_primary     dual
_audit_creation_method
;
Olex2 1.2
(compiled 2017.08.10 svn.r3458 for OlexSys, GUI svn.r5381)
;
_cell_angle_alpha                90
_cell_angle_beta                 100.058(4)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   21.7297(16)
_cell_length_b                   6.5797(5)
_cell_length_c                   10.2247(8)
_cell_measurement_reflns_used    6326
_cell_measurement_temperature    150
_cell_measurement_theta_max      60.624
_cell_measurement_theta_min      3.595
_cell_volume                     1439.41(19)
_computing_cell_refinement
;
SAINT (Bruker, 2013)
;
_computing_data_collection
;
APEX2 (Bruker, 2013)
;
_computing_data_reduction
;
SAINT (Bruker, 2013)
;
_computing_molecular_graphics
;
OLEX2 (Dolomanov et al., 2009) and Mercury (Macrae et
al.,
2008)
;
_computing_publication_material
;
OLEX2 (Dolomanov et al., 2009) and publCIF
(Westrip,
2010)
;
_computing_structure_refinement
;
ShelXL2018 (Sheldrick, 2015b)
;
_computing_structure_solution
;
ShelXT (Sheldrick, 2015a)
;
_diffrn_ambient_temperature      150
_diffrn_detector                 'CMOS Area detector'
_diffrn_detector_area_resol_mean 10.24
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device       'k-geometry diffractometer'
_diffrn_measurement_device_type  'Bruker Venture Metaljet'
_diffrn_measurement_method       'ω and φ scans'
_diffrn_radiation_monochromator  'Helios MX Mirror Optics'
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           GaK\a
_diffrn_radiation_wavelength     1.34139
_diffrn_reflns_av_R_equivalents  0.0517
_diffrn_reflns_av_unetI/netI     0.0329
_diffrn_reflns_limit_h_max       27
_diffrn_reflns_limit_h_min       -28
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            9647
_diffrn_reflns_theta_full        53.594
_diffrn_reflns_theta_max         60.683
_diffrn_reflns_theta_min         3.594
_diffrn_source                   'Metal Jet'
_exptl_absorpt_coefficient_mu    1.208
_exptl_absorpt_correction_T_max  0.7519
_exptl_absorpt_correction_T_min  0.5468
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
(SADABS; Krause et al., 2015)
;
_exptl_crystal_colour            'clear light orange'
_exptl_crystal_density_diffrn    1.911
_exptl_crystal_description       Plate
_exptl_crystal_F_000             816
_exptl_crystal_size_max          0.15
_exptl_crystal_size_mid          0.08
_exptl_crystal_size_min          0.04
_refine_diff_density_max         0.254
_refine_diff_density_min         -0.306
_refine_ls_extinction_coef       0.0040(7)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method
;
SHELXL-2018/3 (Sheldrick, 2015b)
;
_refine_ls_goodness_of_fit_ref   1.061
_refine_ls_hydrogen_treatment    refall
_refine_ls_matrix_type           full
_refine_ls_number_parameters     132
_refine_ls_number_reflns         1656
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.061
_refine_ls_R_factor_all          0.0679
_refine_ls_R_factor_gt           0.0568
_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)+(0.0917P)²+1.5671P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1574
_refine_ls_wR_factor_ref         0.1712
_reflns_number_gt                1339
_reflns_number_total             1656
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            wm5460sup1.cif
_cod_data_source_block           II
_cod_database_code               2242648
_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   0.840
_shelx_estimated_absorpt_t_max   0.953
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'
'-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_type_symbol
_atom_site_label
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_calc_flag
_atom_site_occupancy
N N1 0.52881(9) 1.1272(3) 0.2701(2) 0.0493(5) Uani d 1
C C1 0.56365(10) 0.9427(4) 0.3044(2) 0.0451(5) Uani d 1
O O1 0.74933(8) 0.5029(3) 0.46997(18) 0.0550(5) Uani d 1
C C2 0.62039(10) 0.9234(4) 0.2592(2) 0.0466(6) Uani d 1
F F2 0.63497(7) 1.0570(3) 0.17121(15) 0.0598(5) Uani d 1
O O2 0.66949(9) 0.2838(3) 0.4540(2) 0.0601(5) Uani d 1
H H2 0.699(2) 0.185(8) 0.473(5) 0.142(19) Uiso d 1
F F3 0.71428(7) 0.7543(2) 0.25407(15) 0.0604(5) Uani d 1
C C3 0.66112(10) 0.7681(4) 0.3031(2) 0.0486(6) Uani d 1
C C4 0.64750(10) 0.6250(4) 0.3932(2) 0.0460(6) Uani d 1
C C5 0.59134(11) 0.6440(4) 0.4392(2) 0.0464(5) Uani d 1
F F5 0.57659(7) 0.5188(2) 0.53098(15) 0.0570(5) Uani d 1
C C6 0.54993(10) 0.8009(4) 0.3945(2) 0.0457(5) Uani d 1
F F6 0.49705(6) 0.8153(2) 0.44498(14) 0.0529(4) Uani d 1
C C7 0.69243(11) 0.4589(4) 0.4432(2) 0.0470(6) Uani d 1
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0140 0.0070 '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 0.0580 0.0410 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0250 0.0140 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0390 0.0250 '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_site_symmetry_1
_geom_angle
N1 N1 C1 2_655 122.30(12)
C2 C1 N1 . 117.0(2)
C6 C1 N1 . 124.5(2)
C6 C1 C2 . 117.7(2)
F2 C2 C1 . 119.3(2)
F2 C2 C3 . 119.6(2)
C3 C2 C1 . 121.0(2)
C7 O2 H2 . 114(3)
C2 C3 C4 . 121.5(2)
F3 C3 C2 . 118.4(2)
F3 C3 C4 . 120.1(2)
C3 C4 C5 . 117.8(2)
C3 C4 C7 . 121.4(2)
C5 C4 C7 . 120.7(2)
C4 C5 C6 . 120.8(2)
F5 C5 C4 . 121.2(2)
F5 C5 C6 . 118.0(2)
C1 C6 C5 . 121.2(2)
F6 C6 C1 . 120.5(2)
F6 C6 C5 . 118.2(2)
O1 C7 O2 . 125.4(2)
O1 C7 C4 . 117.8(2)
O2 C7 C4 . 116.8(2)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_site_symmetry_2
_geom_bond_distance
N1 N1 2_655 1.248(4)
N1 C1 . 1.441(3)
C1 C2 . 1.396(3)
C1 C6 . 1.380(3)
O1 C7 . 1.253(3)
C2 F2 . 1.335(3)
C2 C3 . 1.374(3)
O2 H2 . 0.90(5)
O2 C7 . 1.268(3)
F3 C3 . 1.340(3)
C3 C4 . 1.385(3)
C4 C5 . 1.388(3)
C4 C7 . 1.495(3)
C5 F5 . 1.329(3)
C5 C6 . 1.393(3)
C6 F6 . 1.343(3)
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_site_symmetry_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_publ_flag
O2 H2 O1 7_656 0.90(5) 1.71(5) 2.607(2) 173(5) yes
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_site_symmetry_1
_geom_torsion
N1 N1 C1 C2 2_655 136.0(3)
N1 N1 C1 C6 2_655 -54.6(4)
N1 C1 C2 F2 . -10.4(3)
N1 C1 C2 C3 . 170.2(2)
N1 C1 C6 C5 . -169.2(2)
N1 C1 C6 F6 . 8.4(3)
C1 C2 C3 F3 . 178.5(2)
C1 C2 C3 C4 . 0.2(4)
C2 C1 C6 C5 . 0.1(3)
C2 C1 C6 F6 . 177.73(19)
C2 C3 C4 C5 . -0.6(3)
C2 C3 C4 C7 . -178.6(2)
F2 C2 C3 F3 . -1.0(3)
F2 C2 C3 C4 . -179.3(2)
F3 C3 C4 C5 . -178.8(2)
F3 C3 C4 C7 . 3.1(3)
C3 C4 C5 F5 . -176.40(19)
C3 C4 C5 C6 . 0.8(3)
C3 C4 C7 O1 . 40.6(3)
C3 C4 C7 O2 . -138.9(2)
C4 C5 C6 C1 . -0.6(3)
C4 C5 C6 F6 . -178.21(19)
C5 C4 C7 O1 . -137.4(2)
C5 C4 C7 O2 . 43.1(3)
F5 C5 C6 C1 . 176.7(2)
F5 C5 C6 F6 . -1.0(3)
C6 C1 C2 F2 . 179.49(19)
C6 C1 C2 C3 . 0.1(3)
C7 C4 C5 F5 . 1.7(3)
C7 C4 C5 C6 . 178.8(2)

_cod_database_fobs_code 2242648
