#------------------------------------------------------------------------------
#$Date: 2016-02-18 17:37:37 +0200 (Thu, 18 Feb 2016) $
#$Revision: 176729 $
#$URL: svn://www.crystallography.net/cod/cif/1/51/61/1516161.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_1516161
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 F8 I2 N6'
_chemical_formula_weight         762.14
_chemical_name_systematic
; 
 ? 
;
_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_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 120.6230(10)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   28.722(4)
_cell_length_b                   5.1901(7)
_cell_length_c                   18.220(3)
_cell_measurement_reflns_used    5971
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      28.04
_cell_measurement_theta_min      2.26
_cell_volume                     2337.3(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-97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      100(2)
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.946
_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  0.0267
_diffrn_reflns_av_sigmaI/netI    0.0225
_diffrn_reflns_limit_h_max       37
_diffrn_reflns_limit_h_min       -38
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_k_min       -6
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_number            12549
_diffrn_reflns_theta_full        26.00
_diffrn_reflns_theta_max         28.28
_diffrn_reflns_theta_min         1.65
_exptl_absorpt_coefficient_mu    2.781
_exptl_absorpt_correction_T_max  0.8781
_exptl_absorpt_correction_T_min  0.3702
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   SADABS
_exptl_crystal_colour            orange
_exptl_crystal_density_diffrn    2.166
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       needle
_exptl_crystal_F_000             1440
_exptl_crystal_size_max          0.45
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.05
_refine_diff_density_max         0.871
_refine_diff_density_min         -0.363
_refine_diff_density_rms         0.090
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.042
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     172
_refine_ls_number_reflns         2737
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.042
_refine_ls_R_factor_all          0.0266
_refine_ls_R_factor_gt           0.0214
_refine_ls_shift/su_max          0.007
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0191P)²+6.7143P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0476
_refine_ls_wR_factor_ref         0.0498
_reflns_number_gt                2428
_reflns_number_total             2737
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            c4sc00987h6.cif
_cod_data_source_block           (cis-2)(trans-ape)
_cod_depositor_comments
;
The following automatic conversions were performed:

'_symmetry_cell_setting' value 'Monoclinic' changed to 'monoclinic'
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        2337.2(6)
_cod_original_sg_symbol_H-M      C2/c
_cod_database_code               1516161
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
_atom_site_refinement_flags
I1 I 0.887595(7) 0.77797(3) 0.391248(10) 0.01986(6) Uani 1 1 d .
F1 F 0.87498(6) -0.0015(3) 0.18672(10) 0.0277(4) Uani 1 1 d .
F2 F 0.83357(6) 0.3615(3) 0.24255(10) 0.0279(4) Uani 1 1 d .
F3 F 1.01081(6) 0.6526(3) 0.43797(9) 0.0254(3) Uani 1 1 d .
F4 F 1.05146(6) 0.2909(3) 0.38073(10) 0.0236(3) Uani 1 1 d .
N1 N 0.98224(9) -0.0893(4) 0.26013(14) 0.0208(4) Uani 1 1 d .
N2 N 0.66561(9) 0.6232(4) 0.06181(15) 0.0232(5) Uani 1 1 d .
N3 N 0.75940(10) 1.2039(5) 0.03588(15) 0.0266(5) Uani 1 1 d .
C1 C 0.92094(10) 0.5147(5) 0.34268(16) 0.0184(5) Uani 1 1 d .
C2 C 0.88747(10) 0.3510(5) 0.27705(16) 0.0194(5) Uani 1 1 d .
C3 C 0.90829(10) 0.1640(5) 0.24736(16) 0.0188(5) Uani 1 1 d .
C4 C 0.96361(10) 0.1416(5) 0.28053(15) 0.0170(5) Uani 1 1 d .
C5 C 0.99750(10) 0.3102(5) 0.34535(16) 0.0174(5) Uani 1 1 d .
C6 C 0.97625(10) 0.4926(5) 0.37552(15) 0.0181(5) Uani 1 1 d .
C7 C 0.71515(11) 0.6900(5) 0.12459(18) 0.0257(6) Uani 1 1 d .
H7 H 0.7299 0.6009 0.1774 0.031 Uiso 1 1 calc R
C8 C 0.74578(11) 0.8798(6) 0.11703(18) 0.0274(6) Uani 1 1 d .
H8 H 0.7805 0.9230 0.1637 0.033 Uiso 1 1 calc R
C9 C 0.72482(11) 1.0072(5) 0.03949(18) 0.0226(5) Uani 1 1 d .
C10 C 0.64593(11) 0.7479(5) -0.01236(17) 0.0237(5) Uani 1 1 d .
H10 H 0.6109 0.7027 -0.0576 0.028 Uiso 1 1 calc R
C11 C 0.67394(11) 0.9402(5) -0.02689(17) 0.0237(6) Uani 1 1 d .
H11 H 0.6587 1.0233 -0.0808 0.028 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
N1 N1 C4 122.97(13) 2_755
C10 N2 C7 117.1(2) .
N3 N3 C9 112.5(3) 7_675
C2 C1 C6 117.5(2) .
C2 C1 I1 119.90(18) .
C6 C1 I1 122.58(19) .
F2 C2 C1 120.6(2) .
F2 C2 C3 118.0(2) .
C1 C2 C3 121.4(2) .
F1 C3 C2 120.1(2) .
F1 C3 C4 118.9(2) .
C2 C3 C4 121.0(2) .
C3 C4 C5 117.9(2) .
C3 C4 N1 116.9(2) .
C5 C4 N1 123.5(2) .
F4 C5 C6 119.6(2) .
F4 C5 C4 119.8(2) .
C6 C5 C4 120.5(2) .
F3 C6 C5 118.2(2) .
F3 C6 C1 120.1(2) .
C5 C6 C1 121.7(2) .
N2 C7 C8 123.8(3) .
C7 C8 C9 118.4(3) .
C11 C9 C8 119.1(2) .
C11 C9 N3 125.4(2) .
C8 C9 N3 115.4(2) .
N2 C10 C11 123.6(3) .
C9 C11 C10 118.0(2) .
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(2) .
F1 C3 1.340(3) .
F2 C2 1.343(3) .
F3 C6 1.349(3) .
F4 C5 1.345(3) .
N1 N1 1.249(4) 2_755
N1 C4 1.436(3) .
N2 C10 1.337(4) .
N2 C7 1.340(4) .
N3 N3 1.229(5) 7_675
N3 C9 1.449(3) .
C1 C2 1.380(4) .
C1 C6 1.388(4) .
C2 C3 1.387(4) .
C3 C4 1.387(4) .
C4 C5 1.392(3) .
C5 C6 1.383(3) .
C7 C8 1.374(4) .
C8 C9 1.389(4) .
C9 C11 1.385(4) .
C10 C11 1.389(4) .
