#------------------------------------------------------------------------------
#$Date: 2016-02-20 02:53:41 +0200 (Sat, 20 Feb 2016) $
#$Revision: 176768 $
#$URL: svn://www.crystallography.net/cod/cif/2/10/57/2105728.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_2105728
loop_
_publ_author_name
'Saccone, Marco'
'Terraneo, Giancarlo'
'Pilati, Tullio'
'Cavallo, Gabriella'
'Priimagi, Arri'
'Metrangolo, Pierangelo'
'Resnati, Giuseppe'
_publ_section_title
;
 Azobenzene-based difunctional halogen-bond donor: towards the engineering
 of photoresponsive co-crystals
;
_journal_coeditor_code           BI5016
_journal_issue                   1
_journal_name_full               'Acta Crystallographica Section B'
_journal_page_first              149
_journal_page_last               156
_journal_paper_doi               10.1107/S205252061302622X
_journal_volume                  70
_journal_year                    2014
_chemical_formula_moiety         'C12 F8 I2 N2, C2 H6 O S'
_chemical_formula_sum            'C14 H6 F8 I2 N2 O S'
_chemical_formula_weight         656.07
_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                 111.347(12)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   21.140(3)
_cell_length_b                   10.0766(16)
_cell_length_c                   9.5589(15)
_cell_measurement_reflns_used    6005
_cell_measurement_temperature    103(2)
_cell_measurement_theta_max      24.86
_cell_measurement_theta_min      2.27
_cell_volume                     1896.5(5)
_computing_cell_refinement       'SAINT (Bruker, 2008)'
_computing_data_collection       'APEX2 (Bruker, 2008)'
_computing_data_reduction        SAINT
_computing_molecular_graphics    'Mercury (Macrae et al., 2008)'
_computing_publication_material  SHELXL-97
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_structure_solution    'SIR2002 (Burla et al., 2003)'
_diffrn_ambient_temperature      103(2)
_diffrn_measured_fraction_theta_full 0.993
_diffrn_measured_fraction_theta_max 0.993
_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  0.0316
_diffrn_reflns_av_sigmaI/netI    0.0229
_diffrn_reflns_limit_h_max       24
_diffrn_reflns_limit_h_min       -25
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_number            12815
_diffrn_reflns_theta_full        25.01
_diffrn_reflns_theta_max         25.01
_diffrn_reflns_theta_min         3.48
_diffrn_standards_decay_%        0.00
_exptl_absorpt_coefficient_mu    3.510
_exptl_absorpt_correction_T_max  0.6022
_exptl_absorpt_correction_T_min  0.5181
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS (Bruker, 2008)'
_exptl_crystal_colour            orange
_exptl_crystal_density_diffrn    2.298
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       lamina
_exptl_crystal_F_000             1224
_exptl_crystal_size_max          0.40
_exptl_crystal_size_mid          0.10
_exptl_crystal_size_min          0.03
_refine_diff_density_max         0.834
_refine_diff_density_min         -1.191
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.076
_refine_ls_hydrogen_treatment    noref
_refine_ls_matrix_type           full
_refine_ls_number_parameters     137
_refine_ls_number_reflns         1662
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.076
_refine_ls_R_factor_all          0.0399
_refine_ls_R_factor_gt           0.0270
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0260P)²+10.7129P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0579
_refine_ls_wR_factor_ref         0.0650
_reflns_number_gt                1379
_reflns_number_total             1662
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            bi5016sup1.cif
_cod_data_source_block           2_dmso
_cod_original_sg_symbol_H-M      'C 2/c'
_cod_database_code               2105728
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_type_symbol
_atom_site_label
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_disorder_assembly
_atom_site_disorder_group
I I1 0.928736(15) 1.17322(3) 1.02513(4) 0.03522(13) Uani d . 1 1 . .
F F1 0.81527(13) 1.2003(2) 0.6927(3) 0.0358(6) Uani d . 1 1 . .
F F2 0.74142(13) 1.0229(3) 0.4973(3) 0.0348(6) Uani d . 1 1 . .
F F3 0.84236(15) 0.6785(3) 0.8460(3) 0.0418(7) Uani d . 1 1 . .
F F4 0.91586(14) 0.8587(3) 1.0427(3) 0.0391(7) Uani d . 1 1 . .
N N1 0.7567(2) 0.7375(4) 0.5677(4) 0.0335(9) Uani d . 1 1 . .
C C1 0.8234(2) 1.0705(4) 0.7321(5) 0.0283(10) Uani d . 1 1 . .
C C2 0.7852(2) 0.9786(5) 0.6296(5) 0.0302(11) Uani d . 1 1 . .
C C3 0.7914(2) 0.8438(4) 0.6643(5) 0.0301(11) Uani d . 1 1 . .
C C4 0.8352(2) 0.8074(4) 0.8064(5) 0.0327(11) Uani d . 1 1 . .
C C5 0.8738(2) 0.9003(5) 0.9066(5) 0.0311(11) Uani d . 1 1 . .
C C6 0.8693(2) 1.0349(5) 0.8715(5) 0.0312(11) Uani d . 1 1 . .
S S7 0.50223(13) 0.9893(2) 0.1722(3) 0.0317(5) Uani d P 0.50 1 A -1
O O1 0.5069(6) 0.8464(6) 0.2163(9) 0.042(3) Uani d P 0.50 1 A -1
C C7 0.5689(4) 1.0615(7) 0.2991(8) 0.072(2) Uani d . 1 1 A -1
H H7A 0.5625 1.1579 0.2937 0.108 Uiso calc PR 0.50 1 A -1
H H7B 0.6099 1.0390 0.2793 0.108 Uiso calc PR 0.50 1 A -1
H H7C 0.5736 1.0303 0.3995 0.108 Uiso calc PR 0.50 1 A -1
H H7D 0.6015 0.9935 0.3547 0.108 Uiso calc PR 0.50 1 A -1
H H7E 0.5541 1.1125 0.3691 0.108 Uiso calc PR 0.50 1 A -1
H H7F 0.5904 1.1212 0.2488 0.108 Uiso calc PR 0.50 1 A -1
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'
O O 0.0106 0.0060 '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'
S S 0.1246 0.1234 '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_site_symmetry_1
_geom_angle
N1 N1 C3 7_666 112.9(5)
F1 C1 C2 . 118.0(4)
F1 C1 C6 . 119.6(4)
C2 C1 C6 . 122.5(4)
F2 C2 C1 . 118.2(4)
F2 C2 C3 . 121.4(4)
C1 C2 C3 . 120.4(4)
C4 C3 C2 . 117.6(4)
C4 C3 N1 . 115.9(4)
C2 C3 N1 . 126.5(4)
F3 C4 C5 . 118.9(4)
F3 C4 C3 . 119.8(4)
C5 C4 C3 . 121.2(4)
F4 C5 C4 . 118.5(4)
F4 C5 C6 . 119.9(4)
C4 C5 C6 . 121.6(4)
C1 C6 C5 . 116.7(4)
C1 C6 I1 . 122.6(3)
C5 C6 I1 . 120.7(4)
O1 S7 C7 . 105.4(5)
H7A C7 H7B . 109.6
H7A C7 H7C . 109.4
H7B C7 H7C . 109.5
H7D C7 H7E . 109.4
H7D C7 H7F . 109.6
H7E C7 H7F . 109.5
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_site_symmetry_2
_geom_bond_distance
I1 C6 . 2.083(5)
F1 C1 . 1.355(5)
F2 C2 . 1.343(5)
F3 C4 . 1.346(5)
F4 C5 . 1.347(5)
N1 N1 7_666 1.246(7)
N1 C3 . 1.430(6)
C1 C2 . 1.376(7)
C1 C6 . 1.379(6)
C2 C3 . 1.393(6)
C3 C4 . 1.386(7)
C4 C5 . 1.375(7)
C5 C6 . 1.392(7)
S7 O1 . 1.493(6)
S7 C7 . 1.656(7)
C7 H7A . 0.9800
C7 H7B . 0.9800
C7 H7C . 0.9800
C7 H7D . 0.9800
C7 H7E . 0.9800
C7 H7F . 0.9800
loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion_site_symmetry_1
_geom_torsion
F1 C1 C2 F2 . -0.8(6)
C6 C1 C2 F2 . 179.4(4)
F1 C1 C2 C3 . -179.9(4)
C6 C1 C2 C3 . 0.4(7)
F2 C2 C3 C4 . -176.7(4)
C1 C2 C3 C4 . 2.3(6)
F2 C2 C3 N1 . 3.1(7)
C1 C2 C3 N1 . -177.9(4)
N1 N1 C3 C4 7_666 -150.3(5)
N1 N1 C3 C2 7_666 29.9(7)
C2 C3 C4 F3 . 179.2(4)
N1 C3 C4 F3 . -0.6(6)
C2 C3 C4 C5 . -3.4(7)
N1 C3 C4 C5 . 176.8(4)
F3 C4 C5 F4 . -2.0(6)
C3 C4 C5 F4 . -179.5(4)
F3 C4 C5 C6 . 179.2(4)
C3 C4 C5 C6 . 1.8(7)
F1 C1 C6 C5 . 178.2(4)
C2 C1 C6 C5 . -2.0(6)
F1 C1 C6 I1 . -1.1(6)
C2 C1 C6 I1 . 178.7(3)
F4 C5 C6 C1 . -177.8(4)
C4 C5 C6 C1 . 1.0(6)
F4 C5 C6 I1 . 1.6(6)
C4 C5 C6 I1 . -179.7(3)
