Halogen bonding stabilizes a <i>cis</i>-azobenzene derivative in the solid state: a crystallographic study
Saccone, Marco; Siiskonen, Antti; Fernandez-Palacio, Franisco; Priimagi, Arri; Terraneo, Giancarlo; Resnati, Giuseppe; Metrangolo, Pierangelo; Acta Crystallographica Section B 73 (2017) 227–233; doi:10.1107/S2052520617003444

data_2108116
_publ_section_title
;
 Halogen bonding stabilizes a <i>cis</i>-azobenzene derivative in the
 solid state: a crystallographic study
;
_journal_issue                   2
_journal_name_full               'Acta Crystallographica Section B'
_journal_page_first              227
_journal_page_last               233
_journal_paper_doi               10.1107/S2052520617003444
_journal_volume                  73
_journal_year                    2017
_chemical_formula_moiety         'C24 H29 F4 I N2 O'
_chemical_formula_sum            'C24 H29 F4 I N2 O'
_chemical_formula_weight         564.39
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 1 21/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 109.255(16)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   8.5802(16)
_cell_length_b                   33.663(5)
_cell_length_c                   8.752(2)
_cell_measurement_reflns_used    7540
_cell_measurement_temperature    103(2)
_cell_measurement_theta_max      26.85
_cell_measurement_theta_min      2.59
_cell_volume                     2386.5(8)
_computing_cell_refinement       'Bruker SAINT'
_computing_data_collection       'Bruker APEX2'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics
;
ORTEP-3 (Farrugia, L.J. (1997) Jour. Appl. Cryst. 30, 565)
Mercury (Macrae, C. F., Edgington, P. R., McCabe, P., Pidcock, E.,
Shields, G. P., Taylor, R., Towler, M. & van de Streek, J. (2006).
J. Appl. Cryst. 39, 453-457
;
_computing_publication_material  SHELXL
_computing_structure_refinement
;
SHELXL (Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122)
;
_computing_structure_solution
;
SHELXS (Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122)
;
_diffrn_ambient_temperature      103(2)
_diffrn_measured_fraction_theta_full 0.994
_diffrn_measured_fraction_theta_max 0.923
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0465
_diffrn_reflns_av_sigmaI/netI    0.0534
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       42
_diffrn_reflns_limit_k_min       -43
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_number            25224
_diffrn_reflns_theta_full        25.50
_diffrn_reflns_theta_max         27.52
_diffrn_reflns_theta_min         2.42
_diffrn_standards_decay_%        0.00
_exptl_absorpt_coefficient_mu    1.391
_exptl_absorpt_correction_T_max  0.8621
_exptl_absorpt_correction_T_min  0.7911
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
'Bruker (2001). SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.'
_exptl_crystal_colour            orange
_exptl_crystal_density_diffrn    1.571
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       lamina
_exptl_crystal_F_000             1136
_exptl_crystal_size_max          0.20
_exptl_crystal_size_mid          0.10
_exptl_crystal_size_min          0.05
_refine_diff_density_max         0.574
_refine_diff_density_min         -0.986
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.047
_refine_ls_hydrogen_treatment    noref
_refine_ls_matrix_type           full
_refine_ls_number_parameters     290
_refine_ls_number_reflns         5073
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.047
_refine_ls_R_factor_all          0.0633
_refine_ls_R_factor_gt           0.0367
_refine_ls_shift/su_max          0.004
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0132P)^2^+3.0191P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0534
_refine_ls_wR_factor_ref         0.0587
_reflns_number_gt                3840
_reflns_number_total             5073
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            bm5091sup1.cif
_cod_data_source_block           ico281_4
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               2108116
_cod_database_fobs_code          2108116