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_7118709
_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_sum            'C6 F5 N'
_chemical_formula_weight         181.07
_space_group_crystal_system      monoclinic
_space_group_IT_number           5
_space_group_name_Hall           'C 2y'
_space_group_name_H-M_alt        'C 1 2 1'
_symmetry_space_group_name_Hall  'C 2y'
_symmetry_space_group_name_H-M   'C 1 2 1'
_atom_sites_solution_hydrogens   .
_audit_creation_method           SHELXL-2014/6
_audit_update_record
;
2015-10-13 deposited with the CCDC.
2015-12-04 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 127.333(4)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   13.770(6)
_cell_length_b                   5.569(3)
_cell_length_c                   9.822(4)
_cell_measurement_temperature    100(2)
_cell_volume                     598.9(5)
_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'
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_computing_structure_solution    'SHELXL-2014/6 (Sheldrick, 2014)'
_diffrn_ambient_temperature      100(2)
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.964
_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  0.0282
_diffrn_reflns_av_unetI/netI     0.0355
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.964
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_h_min       -18
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            3440
_diffrn_reflns_point_group_measured_fraction_full 0.994
_diffrn_reflns_point_group_measured_fraction_max 0.932
_diffrn_reflns_theta_full        25.000
_diffrn_reflns_theta_max         28.164
_diffrn_reflns_theta_min         2.608
_exptl_absorpt_coefficient_mu    0.231
_exptl_absorpt_correction_T_max  0.7457
_exptl_absorpt_correction_T_min  0.5733
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   SADABS
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    2.008
_exptl_crystal_description       needle
_exptl_crystal_F_000             352
_exptl_crystal_recrystallization_method 'Re-crystallisation from solvent: '
_exptl_crystal_size_max          0.896
_exptl_crystal_size_mid          0.177
_exptl_crystal_size_min          0.076
_refine_diff_density_max         0.256
_refine_diff_density_min         -0.173
_refine_diff_density_rms         0.051
_refine_ls_abs_structure_details
;
 Flack x determined using 464 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.5(6)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.049
_refine_ls_hydrogen_treatment    undef
_refine_ls_matrix_type           full
_refine_ls_number_parameters     109
_refine_ls_number_reflns         1370
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.049
_refine_ls_R_factor_all          0.0432
_refine_ls_R_factor_gt           0.0360
_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^)+(0.0390P)^2^+0.2217P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0808
_refine_ls_wR_factor_ref         0.0842
_reflns_Friedel_coverage         0.754
_reflns_Friedel_fraction_full    0.987
_reflns_Friedel_fraction_max     0.892
_reflns_number_gt                1206
_reflns_number_total             1370
_reflns_threshold_expression     'I > 2\s(I)'
_cod_duplicate_entry             7118643
_cod_data_source_file            c5cc08590j2.cif
_cod_data_source_block           AB112_0m
_cod_database_code               7118709
_exptl_absorpt_special_details   SADABS
_shelxl_version_number           2014/6
_shelx_res_checksum              53700
_shelx_hkl_checksum              24865