#------------------------------------------------------------------------------
#$Date: 2016-02-18 17:37:37 +0200 (Thu, 18 Feb 2016) $
#$Revision: 176729 $
#$URL: svn://www.crystallography.net/cod/cif/1/51/61/1516164.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_1516164
loop_
_publ_author_name
'Bushuyev, Oleksandr S.'
'Corkery, T. Christopher'
'Barrett, Christopher J.'
'Friščić, Tomislav'
_publ_section_title
;
 Photo-mechanical azobenzene cocrystals and in situ X-ray diffraction
 monitoring of their optically-induced crystal-to-crystal isomerisation
;
_journal_issue                   8
_journal_name_full               'Chemical Science'
_journal_page_first              3158
_journal_paper_doi               10.1039/c4sc00987h
_journal_volume                  5
_journal_year                    2014
_chemical_formula_sum            'C22 H8 Br2 F8 N6'
_chemical_formula_weight         668.16
_chemical_name_systematic
; 
 ? 
;
_space_group_IT_number           2
_symmetry_cell_setting           triclinic
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   constr
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                94.9560(10)
_cell_angle_beta                 93.4810(10)
_cell_angle_gamma                95.8480(10)
_cell_formula_units_Z            2
_cell_length_a                   5.9081(6)
_cell_length_b                   8.3193(9)
_cell_length_c                   23.198(2)
_cell_measurement_reflns_used    1785
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      25.07
_cell_measurement_theta_min      2.47
_cell_volume                     1127.25(19)
_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      296(2)
_diffrn_measured_fraction_theta_full 0.984
_diffrn_measured_fraction_theta_max 0.984
_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  0.0579
_diffrn_reflns_av_sigmaI/netI    0.0979
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       28
_diffrn_reflns_limit_l_min       -28
_diffrn_reflns_number            7322
_diffrn_reflns_theta_full        26.02
_diffrn_reflns_theta_max         26.02
_diffrn_reflns_theta_min         0.88
_exptl_absorpt_coefficient_mu    3.688
_exptl_absorpt_correction_T_max  0.7208
_exptl_absorpt_correction_T_min  0.4336
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   SADABS
_exptl_crystal_colour            orange
_exptl_crystal_density_diffrn    1.969
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             648
_exptl_crystal_size_max          0.27
_exptl_crystal_size_mid          0.10
_exptl_crystal_size_min          0.10
_refine_diff_density_max         0.410
_refine_diff_density_min         -0.466
_refine_diff_density_rms         0.067
_refine_ls_extinction_coef       0.0060(3)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_ref   0.780
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     344
_refine_ls_number_reflns         4360
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.780
_refine_ls_R_factor_all          0.0672
_refine_ls_R_factor_gt           0.0362
_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)+(0.0132P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0615
_refine_ls_wR_factor_ref         0.0676
_reflns_number_gt                2668
_reflns_number_total             4360
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            c4sc00987h6.cif
_cod_data_source_block           (trans-1)(trans-ape)
_cod_depositor_comments
;
The following automatic conversions were performed:

'_symmetry_cell_setting' value 'Triclinic' changed to 'triclinic'
according to
/usr/data/users/saulius/crontab/automatic-downloads/rss-feeds/RSC/lib/dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.2 from 2011-04-26.

Automatic conversion script
Id: cif_fix_values 2281 2013-09-26 08:29:07Z andrius 

 Adding full bibliography for 1516158--1516167.cif.
;
_cod_original_cell_volume        1127.2(2)
_cod_original_sg_symbol_H-M      P-1
_cod_database_code               1516164
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'
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
_atom_site_refinement_flags
Br1 Br 0.42754(7) 0.77673(5) 0.260746(15) 0.04957(15) Uani 1 1 d .
Br2 Br 0.51459(7) 0.23749(5) 0.228778(15) 0.05134(15) Uani 1 1 d .
C2 C 0.1056(6) 0.7899(5) 0.34762(14) 0.0379(10) Uani 1 1 d .
C5 C 0.3623(6) 1.0213(5) 0.42051(14) 0.0379(10) Uani 1 1 d .
C6 C 0.4388(6) 0.9692(5) 0.36830(15) 0.0391(10) Uani 1 1 d .
C1 C 0.3158(6) 0.8527(5) 0.33066(14) 0.0355(9) Uani 1 1 d .
C3 C 0.0262(6) 0.8400(5) 0.39952(15) 0.0372(10) Uani 1 1 d .
C4 C 0.1515(6) 0.9579(5) 0.43784(14) 0.0339(9) Uani 1 1 d .
F2 F -0.1763(3) 0.7698(3) 0.41243(8) 0.0532(6) Uani 1 1 d .
F4 F 0.6459(3) 1.0351(3) 0.35499(8) 0.0534(6) Uani 1 1 d .
F1 F -0.0226(4) 0.6722(3) 0.31318(8) 0.0578(6) Uani 1 1 d .
F3 F 0.4920(4) 1.1377(3) 0.45532(8) 0.0548(6) Uani 1 1 d .
C9 C 0.8551(7) 0.0764(5) 0.17175(14) 0.0396(10) Uani 1 1 d .
C7 C 0.5945(6) 0.1864(5) 0.10970(16) 0.0418(10) Uani 1 1 d .
C10 C 0.9679(6) 0.0243(5) 0.12492(15) 0.0396(10) Uani 1 1 d .
C11 C 0.8987(6) 0.0516(5) 0.06886(14) 0.0371(10) Uani 1 1 d .
C12 C 0.7072(6) 0.1332(5) 0.06199(15) 0.0395(10) Uani 1 1 d .
C8 C 0.6650(6) 0.1586(5) 0.16486(14) 0.0385(10) Uani 1 1 d .
F9 F 0.6260(4) 0.1667(3) 0.00981(8) 0.0571(7) Uani 1 1 d .
F8 F 0.4120(4) 0.2664(3) 0.09989(9) 0.0586(6) Uani 1 1 d .
F6 F 1.1509(4) -0.0561(3) 0.13442(8) 0.0554(6) Uani 1 1 d .
F7 F 0.9321(4) 0.0455(3) 0.22522(8) 0.0587(7) Uani 1 1 d .
N5 N 0.3040(6) 0.3511(4) 0.33176(13) 0.0520(9) Uani 1 1 d .
C16 C 0.3683(6) 0.5183(5) 0.42180(15) 0.0441(10) Uani 1 1 d .
H15 H 0.4644 0.5945 0.4460 0.053 Uiso 1 1 calc R
C13 C 0.0975(7) 0.2974(5) 0.34884(16) 0.0522(11) Uani 1 1 d .
H18 H 0.0038 0.2222 0.3237 0.063 Uiso 1 1 calc R
C17 C 0.4320(7) 0.4595(5) 0.36829(16) 0.0485(11) Uani 1 1 d .
H14 H 0.5744 0.4986 0.3572 0.058 Uiso 1 1 calc R
C15 C 0.1544(6) 0.4591(5) 0.43823(14) 0.0391(10) Uani 1 1 d .
C14 C 0.0173(6) 0.3472(5) 0.40122(15) 0.0441(10) Uani 1 1 d .
H17 H -0.1259 0.3062 0.4112 0.053 Uiso 1 1 calc R
N6 N 0.6471(6) 0.6662(5) 0.15830(14) 0.0574(10) Uani 1 1 d .
C20 C 0.8950(7) 0.5530(5) 0.06851(15) 0.0415(10) Uani 1 1 d .
C18 C 0.8347(8) 0.5952(6) 0.16846(16) 0.0583(13) Uani 1 1 d .
H21 H 0.8810 0.5836 0.2068 0.070 Uiso 1 1 calc R
C21 C 0.7005(7) 0.6271(5) 0.05666(16) 0.0475(11) Uani 1 1 d .
H24 H 0.6505 0.6410 0.0188 0.057 Uiso 1 1 calc R
C19 C 0.9672(7) 0.5369(5) 0.12487(15) 0.0522(12) Uani 1 1 d .
H20 H 1.0989 0.4890 0.1338 0.063 Uiso 1 1 calc R
C22 C 0.5830(7) 0.6798(5) 0.10324(17) 0.0555(12) Uani 1 1 d .
H23 H 0.4504 0.7279 0.0955 0.067 Uiso 1 1 calc R
N4 N 0.0950(5) 0.5262(4) 0.49392(12) 0.0464(9) Uani 1 1 d .
N3 N 1.0331(5) 0.4903(4) 0.02474(11) 0.0473(9) Uani 1 1 d .
N1 N 0.0939(5) 1.0263(4) 0.49266(12) 0.0468(9) Uani 1 1 d .
N2 N 1.0344(5) -0.0080(4) 0.02501(10) 0.0451(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
F1 C2 C3 118.1(3) .
F1 C2 C1 119.8(3) .
C3 C2 C1 122.1(4) .
F3 C5 C6 119.0(3) .
F3 C5 C4 119.6(3) .
C6 C5 C4 121.3(4) .
F4 C6 C1 120.0(3) .
F4 C6 C5 117.8(4) .
C1 C6 C5 122.3(4) .
C6 C1 C2 116.6(3) .
C6 C1 Br1 121.8(3) .
C2 C1 Br1 121.6(3) .
F2 C3 C2 117.6(3) .
F2 C3 C4 121.1(3) .
C2 C3 C4 121.3(4) .
C3 C4 C5 116.4(3) .
C3 C4 N1 128.9(3) .
C5 C4 N1 114.7(3) .
F7 C9 C10 118.9(3) .
F7 C9 C8 120.1(3) .
C10 C9 C8 121.1(3) .
F8 C7 C8 120.7(3) .
F8 C7 C12 117.6(3) .
C8 C7 C12 121.7(4) .
F6 C10 C9 118.3(3) .
F6 C10 C11 119.7(3) .
C9 C10 C11 122.1(4) .
C10 C11 C12 116.8(3) .
C10 C11 N2 115.5(3) .
C12 C11 N2 127.7(3) .
F9 C12 C11 121.8(3) .
F9 C12 C7 117.3(3) .
C11 C12 C7 120.8(3) .
C7 C8 C9 117.6(3) .
C7 C8 Br2 120.8(3) .
C9 C8 Br2 121.6(3) .
C17 N5 C13 116.5(3) .
C17 C16 C15 117.5(4) .
N5 C13 C14 124.0(4) .
N5 C17 C16 124.5(4) .
C14 C15 C16 119.4(3) .
C14 C15 N4 125.3(3) .
C16 C15 N4 115.3(3) .
C15 C14 C13 118.2(4) .
C18 N6 C22 117.0(4) .
C19 C20 C21 120.0(4) .
C19 C20 N3 116.1(3) .
C21 C20 N3 123.9(3) .
N6 C18 C19 123.8(4) .
C20 C21 C22 117.5(4) .
C20 C19 C18 117.4(4) .
N6 C22 C21 124.3(4) .
N4 N4 C15 113.2(4) 2_566
N3 N3 C20 114.4(4) 2_765
N1 N1 C4 114.8(4) 2_576
N2 N2 C11 115.4(4) 2_755
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
Br1 C1 1.872(3) .
Br2 C8 1.879(3) .
C2 F1 1.345(4) .
C2 C3 1.366(5) .
C2 C1 1.390(5) .
C5 F3 1.347(4) .
C5 C6 1.369(5) .
C5 C4 1.398(4) .
C6 F4 1.353(4) .
C6 C1 1.365(5) .
C3 F2 1.340(4) .
C3 C4 1.386(5) .
C4 N1 1.423(4) .
C9 F7 1.350(3) .
C9 C10 1.370(5) .
C9 C8 1.381(5) .
C7 F8 1.341(4) .
C7 C8 1.368(4) .
C7 C12 1.389(5) .
C10 F6 1.345(4) .
C10 C11 1.384(4) .
C11 C12 1.385(5) .
C11 N2 1.420(4) .
C12 F9 1.337(4) .
N5 C17 1.324(5) .
N5 C13 1.351(4) .
C16 C17 1.382(5) .
C16 C15 1.397(4) .
C13 C14 1.377(5) .
C15 C14 1.372(5) .
C15 N4 1.440(4) .
N6 C18 1.326(5) .
N6 C22 1.328(4) .
C20 C19 1.372(4) .
C20 C21 1.383(5) .
C20 N3 1.437(4) .
C18 C19 1.400(5) .
C21 C22 1.383(5) .
N4 N4 1.220(5) 2_566
N3 N3 1.219(5) 2_765
N1 N1 1.229(5) 2_576
N2 N2 1.229(5) 2_755
