#------------------------------------------------------------------------------
#$Date: 2016-03-22 13:50:58 +0200 (Tue, 22 Mar 2016) $
#$Revision: 178980 $
#$URL: svn://www.crystallography.net/cod/cif/4/12/03/4120382.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_4120382
loop_
_publ_author_name
'Oleksandr S. Bushuyev'
'Anna Tomberg'
'Tomislav Friščić'
'Christopher J. Barrett'
_publ_section_title
;
 Shaping Crystals with Light: Crystal-to-Crystal Isomerization and
 Photomechanical Effect in Fluorinated Azobenzenes
;
_journal_name_full               'Journal of the American Chemical Society'
_journal_page_first              12556
_journal_page_last               12559
_journal_paper_doi               10.1021/ja4063019
_journal_volume                  135
_journal_year                    2013
_chemical_formula_moiety         'C12 Br2 F8 N2'
_chemical_formula_sum            'C12 Br2 F8 N2'
_chemical_formula_weight         483.96
_chemical_name_common            cis-1
_chemical_name_systematic
; 
 cis-dibromooctafluoroazobenzene polymorph 1 
;
_space_group_IT_number           15
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-C 2yc'
_symmetry_space_group_name_H-M   'C 1 2/c 1'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 110.8020(10)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   23.402(2)
_cell_length_b                   5.3155(5)
_cell_length_c                   11.6756(10)
_cell_measurement_reflns_used    4634
_cell_measurement_temperature    150(2)
_cell_measurement_theta_max      28.20
_cell_measurement_theta_min      3.07
_cell_volume                     1357.7(2)
_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-97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      150(2)
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω 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  0.0179
_diffrn_reflns_av_sigmaI/netI    0.0129
_diffrn_reflns_limit_h_max       29
_diffrn_reflns_limit_h_min       -29
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_k_min       -6
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            7084
_diffrn_reflns_theta_full        25.00
_diffrn_reflns_theta_max         26.73
_diffrn_reflns_theta_min         1.86
_exptl_absorpt_coefficient_mu    6.066
_exptl_absorpt_correction_T_max  0.3967
_exptl_absorpt_correction_T_min  0.0576
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   SADABS
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    2.368
_exptl_crystal_description       needle
_exptl_crystal_F_000             912
_exptl_crystal_size_max          0.98
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.19
_refine_diff_density_max         0.443
_refine_diff_density_min         -0.484
_refine_diff_density_rms         0.059
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.060
_refine_ls_hydrogen_treatment    none
_refine_ls_matrix_type           full
_refine_ls_number_parameters     109
_refine_ls_number_reflns         1441
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.060
_refine_ls_R_factor_all          0.0216
_refine_ls_R_factor_gt           0.0200
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0286P)²+1.6348P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0513
_refine_ls_wR_factor_ref         0.0520
_reflns_number_gt                1354
_reflns_number_total             1441
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ja4063019_si_006_1.cif
_cod_data_source_block           cis-1
_cod_database_code               4120382
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y, -z+1/2'
'x+1/2, y+1/2, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y, z-1/2'
'-x+1/2, -y+1/2, -z'
'x+1/2, -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_symmetry_multiplicity
_atom_site_calc_flag
Br1 Br 0.209215(9) 1.20133(4) 0.820223(19) 0.03526(9) Uani 1 1 d
C1 C 0.15030(8) 0.9543(4) 0.80782(17) 0.0280(4) Uani 1 1 d
C2 C 0.10214(9) 0.9167(4) 0.69849(17) 0.0293(4) Uani 1 1 d
C3 C 0.05911(10) 0.7324(4) 0.6877(2) 0.0314(4) Uani 1 1 d
C4 C 0.06350(9) 0.5763(4) 0.7860(2) 0.0346(4) Uani 1 1 d
C5 C 0.11206(10) 0.6158(4) 0.8956(2) 0.0362(5) Uani 1 1 d
C6 C 0.15389(9) 0.8048(4) 0.90751(19) 0.0322(4) Uani 1 1 d
F1 F 0.11832(6) 0.4639(3) 0.99126(13) 0.0519(4) Uani 1 1 d
F2 F 0.01391(6) 0.7006(3) 0.57949(12) 0.0427(3) Uani 1 1 d
F3 F 0.09623(6) 1.0613(3) 0.60127(10) 0.0406(3) Uani 1 1 d
F4 F 0.19856(6) 0.8421(3) 1.01581(11) 0.0437(3) Uani 1 1 d
N1 N 0.02866(9) 0.3479(3) 0.7711(2) 0.0465(5) Uani 1 1 d
loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
Br1 0.02996(13) 0.03530(14) 0.04251(14) -0.00897(8) 0.01532(9) -0.00632(8)
C1 0.0260(9) 0.0282(9) 0.0348(9) -0.0054(8) 0.0170(8) 0.0004(7)
C2 0.0324(10) 0.0305(10) 0.0303(9) -0.0038(8) 0.0178(8) -0.0015(8)
C3 0.0291(10) 0.0316(10) 0.0376(10) -0.0101(8) 0.0169(8) -0.0020(8)
C4 0.0328(10) 0.0233(10) 0.0569(13) -0.0029(9) 0.0273(10) 0.0036(8)
C5 0.0361(11) 0.0338(10) 0.0481(12) 0.0114(9) 0.0267(10) 0.0129(9)
C6 0.0269(10) 0.0388(11) 0.0347(10) -0.0001(8) 0.0157(8) 0.0084(8)
F1 0.0470(8) 0.0527(9) 0.0659(9) 0.0295(7) 0.0322(7) 0.0165(7)
F2 0.0351(7) 0.0537(8) 0.0407(7) -0.0165(6) 0.0154(6) -0.0144(6)
F3 0.0389(7) 0.0517(8) 0.0318(6) 0.0043(5) 0.0133(5) -0.0106(6)
F4 0.0314(6) 0.0651(9) 0.0346(6) 0.0053(6) 0.0119(5) 0.0078(6)
N1 0.0408(10) 0.0249(9) 0.0845(15) 0.0001(9) 0.0355(11) 0.0009(8)
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'
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
C2 C1 C6 118.53(18) .
C2 C1 Br1 120.56(14) .
C6 C1 Br1 120.90(15) .
F3 C2 C3 118.64(18) .
F3 C2 C1 120.31(17) .
C3 C2 C1 121.05(18) .
F2 C3 C2 118.84(19) .
F2 C3 C4 120.34(19) .
C2 C3 C4 120.78(19) .
C3 C4 C5 117.74(19) .
C3 C4 N1 122.1(2) .
C5 C4 N1 118.7(2) .
F1 C5 C6 119.5(2) .
F1 C5 C4 119.1(2) .
C6 C5 C4 121.47(19) .
F4 C6 C5 119.52(19) .
F4 C6 C1 120.13(19) .
C5 C6 C1 120.3(2) .
N1 N1 C4 121.93(12) 2_556
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
Br1 C1 1.8719(19) .
C1 C2 1.385(3) .
C1 C6 1.387(3) .
C2 F3 1.337(2) .
C2 C3 1.378(3) .
C3 F2 1.340(2) .
C3 C4 1.390(3) .
C4 C5 1.393(3) .
C4 N1 1.438(3) .
C5 F1 1.343(2) .
C5 C6 1.375(3) .
C6 F4 1.339(2) .
N1 N1 1.254(4) 2_556
