Azo⋯phenyl stacking: a persistent self-assembly motif guides the assembly of fluorinated cis-azobenzenes into photo-mechanical needle crystals
Bushuyev, Oleksandr S.; Tomberg, Anna; Vinden, Joanna R.; Moitessier, Nicolas; Barrett, Christopher J.; Friščić, Tomislav; Chemical Communications (Cambridge, United Kingdom) 52 (2016) 2103–2106; doi:10.1039/c5cc08590j

data_7118710
_publ_section_title
;
 Azo&#x22EF;phenyl stacking: a persistent self-assembly motif guides the
 assembly of fluorinated cis-azobenzenes into photo-mechanical needle crystals
;
_journal_coden_ASTM              CHCOFS
_journal_issue                   10
_journal_name_full
;
 Chemical Communications (Cambridge, United Kingdom)
;
_journal_page_first              2103
_journal_page_last               2106
_journal_paper_doi               10.1039/c5cc08590j
_journal_volume                  52
_journal_year                    2016
_chemical_formula_moiety         'C12 H2 Br2 F6 N2'
_chemical_formula_sum            'C12 H2 Br2 F6 N2'
_chemical_formula_weight         447.98
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2ybc'
_space_group_name_H-M_alt        'P 1 21/c 1'
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 1 21/c 1'
_atom_sites_solution_hydrogens   geom
_audit_creation_method           SHELXL-2014
_audit_update_record
;
2015-10-13 deposited with the CCDC.
2015-12-04 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 104.541(3)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   11.412(3)
_cell_length_b                   10.891(3)
_cell_length_c                   11.216(3)
_cell_measurement_reflns_used    3510
_cell_measurement_temperature    150(2)
_cell_measurement_theta_max      23.97
_cell_measurement_theta_min      2.95
_cell_volume                     1349.4(6)
_computing_cell_refinement       'Bruker SAINT'
_computing_data_collection       'Bruker APEX2'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-2014 (Sheldrick, 2014)'
_computing_structure_solution    'SHELXS-97 (Sheldrick 2008)'
_diffrn_ambient_temperature      150(2)
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.988
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0737
_diffrn_reflns_av_unetI/netI     0.0653
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.988
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            15542
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.988
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.876
_diffrn_reflns_theta_min         1.844
_exptl_absorpt_coefficient_mu    6.073
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_correction_T_min  0.4179
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   SADABS
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    2.205
_exptl_crystal_description       needle
_exptl_crystal_F_000             848
_exptl_crystal_size_max          0.830
_exptl_crystal_size_mid          0.140
_exptl_crystal_size_min          0.135
_refine_diff_density_max         0.554
_refine_diff_density_min         -0.658
_refine_diff_density_rms         0.100
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.004
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     199
_refine_ls_number_reflns         3185
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.004
_refine_ls_R_factor_all          0.0709
_refine_ls_R_factor_gt           0.0365
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0275P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0690
_refine_ls_wR_factor_ref         0.0772
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2190
_reflns_number_total             3185
_reflns_threshold_expression     'I > 2\s(I)'
_cod_duplicate_entry             7118644
_cod_data_source_file            c5cc08590j2.cif
_cod_data_source_block           mo_Bushuyev6_0ma
_cod_original_cell_volume        1349.3(5)
_cod_database_code               7118710
_shelx_estimated_absorpt_t_min   0.081
_shelx_estimated_absorpt_t_max   0.494
_shelxl_version_number           2014-3
_shelx_res_checksum              84801
_shelx_hkl_checksum              87654