#------------------------------------------------------------------------------
#$Date: 2016-02-18 17:37:37 +0200 (Thu, 18 Feb 2016) $
#$Revision: 176729 $
#$URL: svn://www.crystallography.net/cod/cif/1/51/61/1516165.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_1516165
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 F8 I2 N4'
_chemical_formula_weight         760.16
_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   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                95.7530(10)
_cell_angle_beta                 96.7480(10)
_cell_angle_gamma                95.8280(10)
_cell_formula_units_Z            2
_cell_length_a                   5.8317(6)
_cell_length_b                   8.5364(9)
_cell_length_c                   23.470(3)
_cell_measurement_reflns_used    4009
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      27.32
_cell_measurement_theta_min      2.41
_cell_volume                     1146.8(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      100(2)
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.898
_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  0.0341
_diffrn_reflns_av_sigmaI/netI    0.0465
_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       29
_diffrn_reflns_limit_l_min       -30
_diffrn_reflns_number            13012
_diffrn_reflns_theta_full        25.00
_diffrn_reflns_theta_max         28.34
_diffrn_reflns_theta_min         0.88
_exptl_absorpt_coefficient_mu    2.831
_exptl_absorpt_correction_T_max  0.7767
_exptl_absorpt_correction_T_min  0.4357
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   SADABS
_exptl_crystal_colour            orange
_exptl_crystal_density_diffrn    2.201
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             720
_exptl_crystal_size_max          0.35
_exptl_crystal_size_mid          0.14
_exptl_crystal_size_min          0.09
_refine_diff_density_max         1.465
_refine_diff_density_min         -0.961
_refine_diff_density_rms         0.142
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.989
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     343
_refine_ls_number_reflns         5145
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.989
_refine_ls_R_factor_all          0.0478
_refine_ls_R_factor_gt           0.0315
_refine_ls_shift/su_max          0.003
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0394P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0698
_refine_ls_wR_factor_ref         0.0763
_reflns_number_gt                4079
_reflns_number_total             5145
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            c4sc00987h6.cif
_cod_data_source_block           (trans-2)(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_sg_symbol_H-M      P-1
_cod_database_code               1516165
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
I1 I 0.45076(4) 0.26333(3) 0.260469(10) 0.01445(8) Uani 1 1 d .
I2 I 0.48489(4) 0.26146(3) 0.766295(10) 0.01502(8) Uani 1 1 d .
C1 C 0.3220(6) 0.3491(5) 0.33630(16) 0.0128(8) Uani 1 1 d .
C2 C 0.1158(7) 0.2825(5) 0.35186(16) 0.0137(8) Uani 1 1 d .
C4 C 0.1547(7) 0.4620(5) 0.44008(16) 0.0135(8) Uani 1 1 d .
C5 C 0.3633(7) 0.5262(5) 0.42474(16) 0.0137(8) Uani 1 1 d .
C3 C 0.0307(6) 0.3362(5) 0.40199(16) 0.0134(8) Uani 1 1 d .
C6 C 0.4448(6) 0.4710(5) 0.37439(16) 0.0133(8) Uani 1 1 d .
F4 F -0.0078(4) 0.1577(3) 0.31834(9) 0.0174(5) Uani 1 1 d .
F2 F 0.4915(4) 0.6468(3) 0.45948(9) 0.0183(5) Uani 1 1 d .
F3 F -0.1736(4) 0.2641(3) 0.41225(9) 0.0170(5) Uani 1 1 d .
F1 F 0.6524(4) 0.5413(3) 0.36342(9) 0.0173(5) Uani 1 1 d .
N4 N 0.6464(6) 0.1564(4) 0.16364(15) 0.0205(8) Uani 1 1 d .
C8 C 0.9621(7) 0.0258(5) 0.13066(17) 0.0172(9) Uani 1 1 d .
H8 H 1.0948 -0.0272 0.1400 0.021 Uiso 1 1 calc R
C7 C 0.8888(7) 0.0475(5) 0.07370(16) 0.0141(8) Uani 1 1 d .
C11 C 0.5786(7) 0.1763(5) 0.10876(17) 0.0178(9) Uani 1 1 d .
H11 H 0.4449 0.2293 0.1008 0.021 Uiso 1 1 calc R
C12 C 0.6903(7) 0.1249(5) 0.06283(17) 0.0181(9) Uani 1 1 d .
H12 H 0.6336 0.1418 0.0246 0.022 Uiso 1 1 calc R
C9 C 0.8381(7) 0.0829(5) 0.17343(17) 0.0192(9) Uani 1 1 d .
H9 H 0.8918 0.0693 0.2122 0.023 Uiso 1 1 calc R
N3 N 0.6711(6) 0.1551(4) 0.66801(14) 0.0173(8) Uani 1 1 d .
C18 C 0.6140(7) -0.0216(5) 0.57956(17) 0.0171(9) Uani 1 1 d .
H18 H 0.5179 -0.1037 0.5549 0.020 Uiso 1 1 calc R
C16 C 0.9596(7) 0.1602(5) 0.60276(16) 0.0147(8) Uani 1 1 d .
H16 H 1.1054 0.2057 0.5942 0.018 Uiso 1 1 calc R
C17 C 0.8276(7) 0.0393(5) 0.56466(16) 0.0133(8) Uani 1 1 d .
C15 C 0.8755(7) 0.2129(5) 0.65301(17) 0.0177(9) Uani 1 1 d .
H15 H 0.9678 0.2950 0.6785 0.021 Uiso 1 1 calc R
C13 C 0.5442(7) 0.0400(5) 0.63106(16) 0.0153(8) Uani 1 1 d .
H13 H 0.3982 -0.0020 0.6406 0.018 Uiso 1 1 calc R
C22 C 0.1019(7) 0.4585(5) 0.93257(17) 0.0156(9) Uani 1 1 d .
C19 C 0.3270(7) 0.3500(5) 0.83739(17) 0.0142(8) Uani 1 1 d .
C24 C 0.1401(7) 0.4371(5) 0.83023(15) 0.0129(8) Uani 1 1 d .
C23 C 0.0304(6) 0.4893(5) 0.87643(16) 0.0144(8) Uani 1 1 d .
C21 C 0.2949(7) 0.3729(5) 0.93992(16) 0.0143(8) Uani 1 1 d .
C20 C 0.4011(7) 0.3215(5) 0.89338(17) 0.0157(8) Uani 1 1 d .
F6 F -0.1512(4) 0.5721(3) 0.86675(10) 0.0210(5) Uani 1 1 d .
F7 F 0.3828(4) 0.3391(3) 0.99208(9) 0.0205(5) Uani 1 1 d .
F5 F 0.0593(4) 0.4715(3) 0.77733(9) 0.0188(5) Uani 1 1 d .
F8 F 0.5859(4) 0.2386(3) 0.90340(10) 0.0215(5) Uani 1 1 d .
N1 N 0.0939(5) 0.5316(4) 0.49289(14) 0.0168(7) Uani 1 1 d .
N2 N -0.0257(6) 0.5199(4) 0.97553(14) 0.0192(8) Uani 1 1 d .
C25 C 1.0204(7) -0.0116(5) 0.02764(16) 0.0168(9) Uani 1 1 d .
H25 H 1.1445 -0.0710 0.0384 0.020 Uiso 1 1 calc R
C26 C 0.9047(6) -0.0261(5) 0.51045(16) 0.0146(8) Uani 1 1 d .
H26 H 0.8088 -0.1134 0.4886 0.018 Uiso 1 1 calc R
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'
I I -0.4742 1.8119 '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
C6 C1 C2 116.4(4) .
C6 C1 I1 121.5(3) .
C2 C1 I1 122.0(3) .
F4 C2 C1 119.9(3) .
F4 C2 C3 117.5(3) .
C1 C2 C3 122.6(4) .
C5 C4 C3 116.4(4) .
C5 C4 N1 115.5(3) .
C3 C4 N1 128.1(4) .
F2 C5 C6 118.5(3) .
F2 C5 C4 119.5(3) .
C6 C5 C4 122.0(4) .
F3 C3 C2 117.4(3) .
F3 C3 C4 121.9(3) .
C2 C3 C4 120.6(4) .
F1 C6 C1 120.6(3) .
F1 C6 C5 117.5(3) .
C1 C6 C5 121.8(4) .
C11 N4 C9 116.3(4) .
C9 C8 C7 118.7(4) .
C8 C7 C12 117.8(4) .
C8 C7 C25 119.4(4) .
C12 C7 C25 122.9(3) .
N4 C11 C12 124.3(4) .
C11 C12 C7 118.8(4) .
N4 C9 C8 124.2(4) .
C13 N3 C15 116.6(4) .
C13 C18 C17 118.9(4) .
C15 C16 C17 119.2(4) .
C16 C17 C18 117.5(4) .
C16 C17 C26 123.0(4) .
C18 C17 C26 119.5(4) .
N3 C15 C16 123.9(4) .
N3 C13 C18 123.8(4) .
C23 C22 C21 116.3(4) .
C23 C22 N2 116.0(3) .
C21 C22 N2 127.7(4) .
C24 C19 C20 116.5(4) .
C24 C19 I2 121.4(3) .
C20 C19 I2 122.1(3) .
F5 C24 C23 118.4(3) .
F5 C24 C19 120.2(3) .
C23 C24 C19 121.4(3) .
F6 C23 C24 118.7(3) .
F6 C23 C22 119.1(3) .
C24 C23 C22 122.2(4) .
F7 C21 C20 117.6(3) .
F7 C21 C22 121.8(3) .
C20 C21 C22 120.6(3) .
F8 C20 C21 117.7(3) .
F8 C20 C19 119.4(3) .
C21 C20 C19 122.9(4) .
N1 N1 C4 114.6(4) 2_566
N2 N2 C22 115.5(4) 2_567
C25 C25 C7 125.4(5) 2_755
C26 C26 C17 125.8(5) 2_756
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
I1 C1 2.105(4) .
I2 C19 2.110(4) .
C1 C6 1.381(5) .
C1 C2 1.382(5) .
C2 F4 1.347(4) .
C2 C3 1.384(5) .
C4 C5 1.384(5) .
C4 C3 1.405(5) .
C4 N1 1.419(5) .
C5 F2 1.348(4) .
C5 C6 1.382(5) .
C3 F3 1.343(4) .
C6 F1 1.359(4) .
N4 C11 1.335(5) .
N4 C9 1.344(5) .
C8 C9 1.383(5) .
C8 C7 1.391(5) .
C7 C12 1.400(5) .
C7 C25 1.475(5) .
C11 C12 1.381(5) .
N3 C13 1.340(5) .
N3 C15 1.343(5) .
C18 C13 1.391(5) .
C18 C17 1.397(5) .
C16 C15 1.381(5) .
C16 C17 1.396(5) .
C17 C26 1.475(5) .
C22 C23 1.393(5) .
C22 C21 1.406(5) .
C22 N2 1.412(5) .
C19 C24 1.385(5) .
C19 C20 1.387(5) .
C24 F5 1.346(4) .
C24 C23 1.381(5) .
C23 F6 1.342(4) .
C21 F7 1.341(4) .
C21 C20 1.374(5) .
C20 F8 1.359(4) .
N1 N1 1.266(6) 2_566
N2 N2 1.242(6) 2_567
C25 C25 1.329(8) 2_755
C26 C26 1.321(8) 2_756
