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 <i>cis</i>-configurations
Elkin, Igor; Maris, Thierry; Hildgen, Patrice; Barrett, Christopher J.; Acta Crystallographica Section E 74 (2018) 1486–1490; doi:10.1107/S2056989018012781

data_2242647
_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 <i>cis</i>-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, 2C2 H6 O'
_chemical_formula_moiety         'C14 H2 F8 N2 O4, 2(C2 H6 O)'
_chemical_formula_sum            'C18 H14 F8 N2 O6'
_chemical_formula_weight         506.31
_chemical_name_systematic
;
<i>cis</i>-2,3,5,6,2',3',5',6'-Octafluoro-4,4'-azinodibenzoic acid
ethanol disolvate
;
_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
_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                99.186(8)
_cell_angle_beta                 99.112(8)
_cell_angle_gamma                99.950(8)
_cell_formula_units_Z            2
_cell_length_a                   5.8188(9)
_cell_length_b                   10.4579(16)
_cell_length_c                   17.468(3)
_cell_measurement_reflns_used    9922
_cell_measurement_temperature    150
_cell_measurement_theta_max      55.056
_cell_measurement_theta_min      2.272
_cell_volume                     1014.5(3)
_computing_cell_refinement
;
SAINT (Bruker, 2013)
;
_computing_data_collection
;
APEX2 (Bruker, 2013)
;
_computing_data_reduction
;
SAINT (Bruker, 2013)
;
_computing_molecular_graphics
;
<i>OLEX2</i> (Dolomanov <i>et al.</i>, 2009) and Mercury (Macrae <i>et
al.</i>,
2008)
;
_computing_publication_material
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<i>OLEX2</i> (Dolomanov <i>et al.</i>, 2009) and <i>publCIF</i>
(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 0.995
_diffrn_measured_fraction_theta_max 0.984
_diffrn_measurement_device       'k-geometry diffractometer'
_diffrn_measurement_device_type  'Bruker Venture Metaljet'
_diffrn_measurement_method       '\w and \f 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_unetI/netI     0.0849
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_number            18534
_diffrn_reflns_theta_full        53.594
_diffrn_reflns_theta_max         55.398
_diffrn_reflns_theta_min         2.271
_diffrn_source                   'Metal Jet'
_exptl_absorpt_coefficient_mu    0.981
_exptl_absorpt_correction_T_max  0.7508
_exptl_absorpt_correction_T_min  0.5493
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
(<i>SADABS</i>; Krause <i>et al</i>., 2015)
;
_exptl_crystal_colour            'clear light yellow'
_exptl_crystal_density_diffrn    1.658
_exptl_crystal_description       Platelet
_exptl_crystal_F_000             512
_exptl_crystal_size_max          0.25
_exptl_crystal_size_mid          0.075
_exptl_crystal_size_min          0.03
_refine_diff_density_max         0.488
_refine_diff_density_min         -0.409
_refine_ls_extinction_coef       0.012(3)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_extinction_method
;
SHELXL-2018/3 (Sheldrick, 2015b)
;
_refine_ls_goodness_of_fit_ref   1.067
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     312
_refine_ls_number_reflns         18534
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.067
_refine_ls_R_factor_all          0.1159
_refine_ls_R_factor_gt           0.0930
_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/[\s^2^(Fo^2^)+(0.1107P)^2^+2.0727P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2654
_refine_ls_wR_factor_ref         0.2884
_reflns_number_gt                13265
_reflns_number_total             18534
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            wm5460sup1.cif
_cod_data_source_block           I
_cod_database_code               2242647
_cod_database_fobs_code          2242647
_shelx_estimated_absorpt_t_min   0.792
_shelx_estimated_absorpt_t_max   0.971
_shelx_hkl_checksum              43045
_shelx_res_checksum              41459