#------------------------------------------------------------------------------
#$Date: 2016-02-18 17:37:37 +0200 (Thu, 18 Feb 2016) $
#$Revision: 176729 $
#$URL: svn://www.crystallography.net/cod/cif/1/51/61/1516163.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_1516163
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            'C24 H10 Br2 F8 N4'
_chemical_formula_weight         666.18
_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   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                70.137(2)
_cell_angle_beta                 84.722(2)
_cell_angle_gamma                79.999(2)
_cell_formula_units_Z            1
_cell_length_a                   6.0828(11)
_cell_length_b                   8.3133(15)
_cell_length_c                   12.157(2)
_cell_measurement_reflns_used    2702
_cell_measurement_temperature    150(2)
_cell_measurement_theta_max      27.31
_cell_measurement_theta_min      2.64
_cell_volume                     569.04(17)
_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 0.992
_diffrn_measured_fraction_theta_max 0.985
_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  0.0194
_diffrn_reflns_av_sigmaI/netI    0.0295
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            4568
_diffrn_reflns_theta_full        25.00
_diffrn_reflns_theta_max         26.37
_diffrn_reflns_theta_min         1.78
_exptl_absorpt_coefficient_mu    3.650
_exptl_absorpt_correction_T_max  0.8677
_exptl_absorpt_correction_T_min  0.4280
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   SADABS
_exptl_crystal_colour            red
_exptl_crystal_density_diffrn    1.944
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             324
_exptl_crystal_size_max          0.28
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.04
_refine_diff_density_max         0.373
_refine_diff_density_min         -0.465
_refine_diff_density_rms         0.069
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.043
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     172
_refine_ls_number_reflns         2302
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.043
_refine_ls_R_factor_all          0.0286
_refine_ls_R_factor_gt           0.0238
_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)+(0.0267P)²+0.3035P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0561
_refine_ls_wR_factor_ref         0.0578
_reflns_number_gt                2088
_reflns_number_total             2302
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            c4sc00987h6.cif
_cod_data_source_block           (trans-1)(trans-bpe)
_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        569.04(18)
_cod_original_sg_symbol_H-M      P-1
_cod_database_code               1516163
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 0.30114(4) 0.69017(3) 0.26696(2) 0.02415(8) Uani 1 1 d .
F4 F 0.7823(2) 0.60972(16) 0.18349(12) 0.0286(3) Uani 1 1 d .
F1 F 0.2661(2) 0.36456(17) 0.48233(12) 0.0289(3) Uani 1 1 d .
F2 F 0.5658(2) 0.08808(16) 0.56873(11) 0.0275(3) Uani 1 1 d .
F3 F 1.0888(2) 0.33300(17) 0.27051(12) 0.0287(3) Uani 1 1 d .
N1 N 0.0076(3) 1.0136(2) 0.82788(18) 0.0283(5) Uani 1 1 d .
C1 C 0.3374(4) 0.7244(3) 0.9159(2) 0.0223(5) Uani 1 1 d .
N2 N 1.0234(3) 0.0651(2) 0.45909(18) 0.0268(4) Uani 1 1 d .
C8 C 0.4689(4) 0.3570(3) 0.4280(2) 0.0223(5) Uani 1 1 d .
C11 C 0.8870(4) 0.3392(3) 0.3242(2) 0.0217(5) Uani 1 1 d .
C7 C 0.5152(4) 0.4935(3) 0.3301(2) 0.0208(5) Uani 1 1 d .
C3 C 0.2149(4) 1.0079(3) 0.7812(2) 0.0289(5) Uani 1 1 d .
H3 H 0.2490 1.1044 0.7167 0.035 Uiso 1 1 calc R
C4 C -0.0346(4) 0.8761(3) 0.9191(2) 0.0286(5) Uani 1 1 d .
H4 H -0.1806 0.8784 0.9544 0.034 Uiso 1 1 calc R
C6 C 0.5124(4) 0.5742(3) 0.9579(2) 0.0248(5) Uani 1 1 d .
H6 H 0.6568 0.5839 0.9214 0.030 Uiso 1 1 calc R
C2 C 0.3836(4) 0.8688(3) 0.8218(2) 0.0266(5) Uani 1 1 d .
H2 H 0.5291 0.8718 0.7860 0.032 Uiso 1 1 calc R
C9 C 0.6262(4) 0.2133(3) 0.47318(19) 0.0217(5) Uani 1 1 d .
C5 C 0.1217(4) 0.7306(3) 0.9651(2) 0.0261(5) Uani 1 1 d .
H5 H 0.0821 0.6361 1.0296 0.031 Uiso 1 1 calc R
C10 C 0.8413(4) 0.1999(3) 0.4227(2) 0.0225(5) Uani 1 1 d .
C12 C 0.7279(4) 0.4813(3) 0.27909(19) 0.0225(5) 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
C4 N1 C3 116.7(2) .
C2 C1 C5 117.1(2) .
C2 C1 C6 120.0(2) .
C5 C1 C6 122.9(2) .
N2 N2 C10 114.5(2) 2_756
F1 C8 C9 118.54(19) .
F1 C8 C7 119.63(19) .
C9 C8 C7 121.8(2) .
F3 C11 C12 118.8(2) .
F3 C11 C10 119.43(19) .
C12 C11 C10 121.8(2) .
C8 C7 C12 117.4(2) .
C8 C7 Br1 122.23(17) .
C12 C7 Br1 120.40(16) .
N1 C3 C2 123.7(2) .
N1 C3 H3 118.2 .
C2 C3 H3 118.2 .
N1 C4 C5 123.9(2) .
N1 C4 H4 118.0 .
C5 C4 H4 118.0 .
C6 C6 C1 126.1(3) 2_667
C6 C6 H6 117.0 2_667
C1 C6 H6 117.0 .
C3 C2 C1 119.3(2) .
C3 C2 H2 120.3 .
C1 C2 H2 120.3 .
F2 C9 C8 117.4(2) .
F2 C9 C10 121.31(19) .
C8 C9 C10 121.3(2) .
C4 C5 C1 119.3(2) .
C4 C5 H5 120.4 .
C1 C5 H5 120.4 .
C11 C10 C9 116.5(2) .
C11 C10 N2 114.8(2) .
C9 C10 N2 128.7(2) .
F4 C12 C11 118.7(2) .
F4 C12 C7 120.01(19) .
C11 C12 C7 121.3(2) .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
Br1 C7 1.884(2) .
F4 C12 1.345(2) .
F1 C8 1.347(3) .
F2 C9 1.342(2) .
F3 C11 1.338(3) .
N1 C4 1.338(3) .
N1 C3 1.334(3) .
C1 C2 1.398(3) .
C1 C5 1.391(3) .
C1 C6 1.469(3) .
N2 N2 1.251(4) 2_756
N2 C10 1.414(3) .
C8 C9 1.378(3) .
C8 C7 1.384(3) .
C11 C12 1.376(3) .
C11 C10 1.399(3) .
C7 C12 1.385(3) .
C3 C2 1.388(3) .
C3 H3 0.9500 .
C4 C5 1.385(3) .
C4 H4 0.9500 .
C6 C6 1.331(4) 2_667
C6 H6 0.9500 .
C2 H2 0.9500 .
C9 C10 1.396(3) .
C5 H5 0.9500 .
