#------------------------------------------------------------------------------
#$Date: 2018-08-14 15:13:30 +0300 (Tue, 14 Aug 2018) $
#$Revision: 209676 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/11/87/7118710.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/
#
# All data on this site have been placed in the public domain by the
# contributors.
#
data_7118710
loop_
_publ_author_name
'Bushuyev, Oleksandr S.'
'Tomberg, Anna'
'Vinden, Joanna R.'
'Moitessier, Nicolas'
'Barrett, Christopher J.'
'Friščić, Tomislav'
_publ_section_title
;
 Azo⋯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       'φ and ω 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/[σ²(Fo²)+(0.0275P)²] where P=(Fo²+2Fc²)/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 > 2σ(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
#BEGIN Tags that were not found in dictionaries:
_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   0.081
_shelx_estimated_absorpt_t_max   0.494
_shelxl_version_number           2014-3
#END Tags that were not found in dictionaries
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Br1 Br 0.67702(3) 1.07896(4) 0.59763(4) 0.04170(13) Uani 1 1 d . . . . .
Br2 Br 0.75296(3) 0.46866(3) 0.43534(4) 0.03822(13) Uani 1 1 d . . . . .
F1 F 0.5675(2) 1.12622(19) 0.1232(2) 0.0476(6) Uani 1 1 d . . . . .
F2 F 1.09749(19) 0.6688(2) 0.28038(19) 0.0505(6) Uani 1 1 d . . . . .
F3 F 0.62109(18) 1.21596(17) 0.3541(2) 0.0465(6) Uani 1 1 d . . . . .
F4 F 0.95751(18) 0.47842(18) 0.30813(19) 0.0442(6) Uani 1 1 d . . . . .
F5 F 0.90542(17) 0.91741(18) 0.51659(19) 0.0400(5) Uani 1 1 d . . . . .
F6 F 0.62521(16) 0.72499(16) 0.27859(16) 0.0305(5) Uani 1 1 d . . . . .
N1 N 0.6698(2) 0.8093(3) 0.5229(2) 0.0281(6) Uani 1 1 d . . . . .
N2 N 0.7492(2) 0.7262(2) 0.5432(2) 0.0285(7) Uani 1 1 d . . . . .
C1 C 0.5941(3) 1.0470(3) 0.2187(3) 0.0320(8) Uani 1 1 d . . . . .
C2 C 0.5939(3) 0.9244(3) 0.1971(3) 0.0290(8) Uani 1 1 d . . . . .
H2 H 0.5727 0.8929 0.1155 0.035 Uiso 1 1 calc R U . . .
C3 C 0.6256(3) 0.8468(3) 0.2979(3) 0.0255(8) Uani 1 1 d . . . . .
C4 C 0.6533(3) 0.8892(3) 0.4179(3) 0.0221(7) Uani 1 1 d . . . . .
C5 C 0.8358(3) 0.7157(3) 0.4703(3) 0.0241(7) Uani 1 1 d . . . . .
C6 C 0.9148(3) 0.8094(3) 0.4600(3) 0.0299(8) Uani 1 1 d . . . . .
C7 C 1.0042(3) 0.7968(3) 0.3981(3) 0.0341(9) Uani 1 1 d . . . . .
H1 H 1.0571 0.8628 0.3925 0.041 Uiso 1 1 calc R U . . .
C8 C 1.0138(3) 0.6845(4) 0.3447(3) 0.0347(9) Uani 1 1 d . . . . .
C9 C 0.6215(3) 1.0941(3) 0.3377(3) 0.0309(8) Uani 1 1 d . . . . .
C10 C 0.6471(3) 1.0152(3) 0.4368(3) 0.0294(8) Uani 1 1 d . . . . .
C11 C 0.8526(3) 0.6016(3) 0.4198(3) 0.0268(8) Uani 1 1 d . . . . .
C12 C 0.9404(3) 0.5876(3) 0.3567(3) 0.0335(9) Uani 1 1 d . . . . .
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 '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'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Br Br -0.2901 2.4595 '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
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
N2 N1 C4 121.5(3) . .
N1 N2 C5 121.3(3) . .
F1 C1 C2 119.8(3) . .
F1 C1 C9 118.6(3) . .
C2 C1 C9 121.6(3) . .
C1 C2 C3 117.8(3) . .
C1 C2 H2 121.1 . .
C3 C2 H2 121.1 . .
F6 C3 C4 118.5(3) . .
F6 C3 C2 118.7(3) . .
C4 C3 C2 122.7(3) . .
C3 C4 C10 118.0(3) . .
C3 C4 N1 123.1(3) . .
C10 C4 N1 118.2(3) . .
C6 C5 C11 117.5(3) . .
C6 C5 N2 123.0(3) . .
C11 C5 N2 119.0(3) . .
F5 C6 C7 118.6(3) . .
F5 C6 C5 118.1(3) . .
C7 C6 C5 123.3(3) . .
C6 C7 C8 117.2(3) . .
C6 C7 H1 121.4 . .
C8 C7 H1 121.4 . .
F2 C8 C12 119.2(3) . .
F2 C8 C7 119.3(3) . .
C12 C8 C7 121.5(3) . .
F3 C9 C10 121.0(3) . .
F3 C9 C1 119.3(3) . .
C10 C9 C1 119.7(3) . .
C9 C10 C4 120.0(3) . .
C9 C10 Br1 119.6(3) . .
C4 C10 Br1 120.4(3) . .
C12 C11 C5 119.9(3) . .
C12 C11 Br2 120.0(3) . .
C5 C11 Br2 120.0(3) . .
F4 C12 C11 120.5(3) . .
F4 C12 C8 119.0(3) . .
C11 C12 C8 120.5(3) . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
Br1 C10 1.882(3) .
Br2 C11 1.876(3) .
F1 C1 1.349(4) .
F2 C8 1.345(4) .
F3 C9 1.340(4) .
F4 C12 1.343(4) .
F5 C6 1.354(4) .
F6 C3 1.344(3) .
N1 N2 1.261(4) .
N1 C4 1.438(4) .
N2 C5 1.437(4) .
C1 C2 1.357(5) .
C1 C9 1.391(5) .
C2 C3 1.386(4) .
C2 H2 0.9500 .
C3 C4 1.382(4) .
C4 C10 1.393(4) .
C5 C6 1.385(4) .
C5 C11 1.399(4) .
C6 C7 1.377(5) .
C7 C8 1.379(5) .
C7 H1 0.9500 .
C8 C12 1.374(5) .
C9 C10 1.377(5) .
C11 C12 1.372(5) .
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
C7 H1 F5 0.95 2.60 3.342(4) 135.7 3_776
C7 H1 F4 0.95 2.55 3.156(4) 122.1 2_755
C7 H1 Br1 0.95 3.07 3.870(4) 142.3 3_776
C2 H2 N2 0.95 2.69 3.216(4) 115.9 4_575
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
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
C4 N1 N2 C5 7.0(4) . . . .
F1 C1 C2 C3 177.9(3) . . . .
C9 C1 C2 C3 -1.9(5) . . . .
C1 C2 C3 F6 179.6(3) . . . .
C1 C2 C3 C4 2.1(5) . . . .
F6 C3 C4 C10 -176.6(3) . . . .
C2 C3 C4 C10 0.9(5) . . . .
F6 C3 C4 N1 -6.5(5) . . . .
C2 C3 C4 N1 171.0(3) . . . .
N2 N1 C4 C3 58.6(4) . . . .
N2 N1 C4 C10 -131.2(3) . . . .
N1 N2 C5 C6 58.5(4) . . . .
N1 N2 C5 C11 -129.8(3) . . . .
C11 C5 C6 F5 -175.0(3) . . . .
N2 C5 C6 F5 -3.3(5) . . . .
C11 C5 C6 C7 3.1(5) . . . .
N2 C5 C6 C7 174.8(3) . . . .
F5 C6 C7 C8 178.0(3) . . . .
C5 C6 C7 C8 -0.1(5) . . . .
C6 C7 C8 F2 178.1(3) . . . .
C6 C7 C8 C12 -2.5(5) . . . .
F1 C1 C9 F3 -0.2(5) . . . .
C2 C1 C9 F3 179.7(3) . . . .
F1 C1 C9 C10 179.0(3) . . . .
C2 C1 C9 C10 -1.2(5) . . . .
F3 C9 C10 C4 -176.6(3) . . . .
C1 C9 C10 C4 4.2(5) . . . .
F3 C9 C10 Br1 2.0(4) . . . .
C1 C9 C10 Br1 -177.1(3) . . . .
C3 C4 C10 C9 -4.0(5) . . . .
N1 C4 C10 C9 -174.7(3) . . . .
C3 C4 C10 Br1 177.4(2) . . . .
N1 C4 C10 Br1 6.7(4) . . . .
C6 C5 C11 C12 -3.7(5) . . . .
N2 C5 C11 C12 -175.7(3) . . . .
C6 C5 C11 Br2 177.7(2) . . . .
N2 C5 C11 Br2 5.6(4) . . . .
C5 C11 C12 F4 179.8(3) . . . .
Br2 C11 C12 F4 -1.5(4) . . . .
C5 C11 C12 C8 1.3(5) . . . .
Br2 C11 C12 C8 179.9(3) . . . .
F2 C8 C12 F4 2.7(5) . . . .
C7 C8 C12 F4 -176.7(3) . . . .
F2 C8 C12 C11 -178.7(3) . . . .
C7 C8 C12 C11 1.9(5) . . . .
