#------------------------------------------------------------------------------
#$Date: 2016-03-26 13:42:56 +0200 (Sat, 26 Mar 2016) $
#$Revision: 180233 $
#$URL: svn://www.crystallography.net/cod/cif/7/11/19/7111933.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_7111933
loop_
_publ_author_name
'Dinesh G. (Dan) Patel'
'Ian M. Walton'
'Jordan M. Cox'
'Cody J. Gleason'
'David R. Butzer'
'Jason B. Benedict'
_publ_section_title
;
 Photoresponsive porous materials: the design and synthesis of
 photochromic diarylethene-based linkers and a metal-organic framework
;
_journal_name_full               Chem.Commun.
_journal_page_first              2653
_journal_paper_doi               10.1039/c3cc49666j
_journal_volume                  50
_journal_year                    2014
_chemical_formula_moiety         'C26 H20 Br2 S2'
_chemical_formula_sum            'C26 H20 Br2 S2'
_chemical_formula_weight         556.36
_chemical_name_systematic
;
 ?
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           15
_space_group_name_Hall           '-C 2yc'
_space_group_name_H-M_alt        'C 1 2/c 1'
_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
_audit_creation_date             2013-11-15
_audit_creation_method
;
Olex2 1.2
(compiled 2013.11.15 svn.r2834 for OlexSys, GUI svn.r4707)
;
_cell_angle_alpha                90
_cell_angle_beta                 94.3179(8)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   9.3043(3)
_cell_length_b                   21.4919(8)
_cell_length_c                   11.0020(4)
_cell_measurement_reflns_used    9884
_cell_measurement_temperature    90
_cell_measurement_theta_max      33.148
_cell_measurement_theta_min      2.391
_cell_volume                     2193.79(13)
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL (Sheldrick, 2008)'
_computing_structure_solution    'XS (Sheldrick, 2008)'
_diffrn_ambient_temperature      90
_diffrn_detector                 'Bruker APEX2 area detector'
_diffrn_detector_area_resol_mean 7.9
_diffrn_detector_type            'CCD area detector'
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_device       'three-circle diffractometer'
_diffrn_measurement_device_type  'Bruker SMART APEX2 area detector'
_diffrn_measurement_method       'ω and φ scans'
_diffrn_radiation_monochromator  'mirror optics'
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_xray_symbol    K-L~3~
_diffrn_reflns_av_R_equivalents  0.0258
_diffrn_reflns_av_unetI/netI     0.0209
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       32
_diffrn_reflns_limit_k_min       -26
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            17072
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 1.000
_diffrn_reflns_theta_full        26.000
_diffrn_reflns_theta_max         33.154
_diffrn_reflns_theta_min         1.895
_diffrn_source                   'microfocus rotating anode'
_diffrn_source_type              'Incoatec I\ms'
_exptl_absorpt_coefficient_mu    3.897
_exptl_absorpt_correction_T_max  0.7465
_exptl_absorpt_correction_T_min  0.7142
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
'SADABS-2012/1 (Bruker,2012) was used for absorption correction. wR2(int) was 0.0728 before and 0.0339 after correction. The Ratio of minimum to maximum transmission is 0.9567. The λ/2 correction factor is 0.0015.'
_exptl_crystal_colour            'clear colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.684
_exptl_crystal_description       block
_exptl_crystal_F_000             1112
_exptl_crystal_recrystallization_method
'Slow cooling of a dimethylformamide solution'
_exptl_crystal_size_max          0.05
_exptl_crystal_size_mid          0.04
_exptl_crystal_size_min          0.02
_refine_diff_density_max         0.628
_refine_diff_density_min         -0.266
_refine_diff_density_rms         0.078
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.085
_refine_ls_hydrogen_treatment    riding
_refine_ls_matrix_type           full
_refine_ls_number_parameters     138
_refine_ls_number_reflns         4186
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.085
_refine_ls_R_factor_all          0.0255
_refine_ls_R_factor_gt           0.0219
_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)+(0.0221P)²+2.9004P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0560
_refine_ls_wR_factor_ref         0.0577
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3845
_reflns_number_total             4186
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            c3cc49666j.txt
_cod_data_source_block           6a
_cod_database_code               7111933
#BEGIN Tags that were not found in dictionaries:
_shelxl_version_number           2013-3
_shelx_space_group_comment
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C1(H1), C3(H3), C4(H4), C9(H9)
2.b Idealised Me refined as rotating group:
 C11(H11A,H11B,H11C), C13(H13A,H13B,H13C)
;
#END Tags that were not found in dictionaries
loop_
_space_group_symop_operation_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_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
Br1 Br -0.00740(2) 0.33895(2) 0.46078(2) 0.01608(4) Uani 1 1 d .
S1 S 0.20168(3) 0.60724(2) 0.26908(3) 0.01286(6) Uani 1 1 d .
C1 C 0.23244(13) 0.39269(5) 0.35677(10) 0.01181(19) Uani 1 1 d .
H1 H 0.1898 0.4302 0.3762 0.014 Uiso 1 1 calc R
C3 C 0.22750(14) 0.27991(6) 0.35335(11) 0.0142(2) Uani 1 1 d .
H3 H 0.1806 0.2429 0.3690 0.017 Uiso 1 1 calc R
C4 C 0.35726(14) 0.27946(5) 0.30087(10) 0.0134(2) Uani 1 1 d .
H4 H 0.3981 0.2415 0.2819 0.016 Uiso 1 1 calc R
C6 C 0.36434(13) 0.39263(5) 0.30056(10) 0.01045(18) Uani 1 1 d .
C9 C 0.42328(12) 0.55756(5) 0.37870(10) 0.01098(18) Uani 1 1 d .
H9 H 0.5056 0.5509 0.4304 0.013 Uiso 1 1 calc R
C8 C 0.36234(12) 0.51118(5) 0.29643(10) 0.00991(18) Uani 1 1 d .
C5 C 0.43022(13) 0.33511(5) 0.27500(10) 0.01073(18) Uani 1 1 d .
C10 C 0.34895(13) 0.61228(5) 0.37389(10) 0.01164(19) Uani 1 1 d .
C7 C 0.43363(12) 0.45074(5) 0.27353(10) 0.01010(18) Uani 1 1 d .
C2 C 0.16746(13) 0.33737(5) 0.38266(10) 0.0128(2) Uani 1 1 d .
C12 C 0.24006(12) 0.53140(5) 0.23083(10) 0.01087(18) Uani 1 1 d .
C11 C 0.38265(16) 0.67147(6) 0.44224(12) 0.0189(2) Uani 1 1 d .
H11A H 0.3677 0.7062 0.3880 0.028 Uiso 1 1 calc GR
H11B H 0.4813 0.6708 0.4748 0.028 Uiso 1 1 calc GR
H11C H 0.3206 0.6753 0.5077 0.028 Uiso 1 1 calc GR
C13 C 0.14960(14) 0.49856(6) 0.13201(11) 0.0157(2) Uani 1 1 d .
H13A H 0.0955 0.4660 0.1672 0.024 Uiso 1 1 calc GR
H13B H 0.2109 0.4810 0.0746 0.024 Uiso 1 1 calc GR
H13C H 0.0845 0.5277 0.0910 0.024 Uiso 1 1 calc GR
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'
Br Br -0.2901 2.4595 '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'
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
_geom_angle_site_symmetry_3
C10 S1 C12 93.08(5) . .
C2 C1 C6 119.97(11) . .
C4 C3 C2 118.65(11) . .
C3 C4 C5 121.84(11) . .
C1 C6 C5 119.32(10) . .
C1 C6 C7 120.24(10) . .
C5 C6 C7 120.41(10) . .
C10 C9 C8 113.56(10) . .
C9 C8 C7 123.59(10) . .
C12 C8 C9 112.63(10) . .
C12 C8 C7 123.37(10) . .
C4 C5 C6 118.44(11) . .
C4 C5 C5 122.29(7) . 2_655
C6 C5 C5 119.27(7) . 2_655
C9 C10 S1 110.27(8) . .
C9 C10 C11 128.78(11) . .
C11 C10 S1 120.93(9) . .
C6 C7 C8 120.49(10) . .
C7 C7 C6 120.29(6) 2_655 .
C7 C7 C8 119.22(6) 2_655 .
C1 C2 Br1 118.97(9) . .
C1 C2 C3 121.69(11) . .
C3 C2 Br1 119.34(9) . .
C8 C12 S1 110.45(8) . .
C8 C12 C13 129.07(10) . .
C13 C12 S1 120.36(9) . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
Br1 C2 1.8967(12) .
S1 C10 1.7266(12) .
S1 C12 1.7273(11) .
C1 C6 1.4152(16) .
C1 C2 1.3735(16) .
C3 C4 1.3770(18) .
C3 C2 1.4028(17) .
C4 C5 1.4147(16) .
C6 C5 1.4175(16) .
C6 C7 1.4466(15) .
C9 C8 1.4342(15) .
C9 C10 1.3633(16) .
C8 C7 1.4886(15) .
C8 C12 1.3713(15) .
C5 C5 1.448(2) 2_655
C10 C11 1.4989(17) .
C7 C7 1.375(2) 2_655
C12 C13 1.5002(16) .
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
_geom_torsion_site_symmetry_4
C1 C6 C5 C4 3.35(16) .
C1 C6 C5 C5 -175.91(12) 2_655
C1 C6 C7 C8 -4.28(16) .
C1 C6 C7 C7 175.64(13) 2_655
C3 C4 C5 C6 -2.12(17) .
C3 C4 C5 C5 177.11(13) 2_655
C4 C3 C2 Br1 -177.57(9) .
C4 C3 C2 C1 2.12(18) .
C6 C1 C2 Br1 178.83(8) .
C6 C1 C2 C3 -0.86(18) .
C9 C8 C7 C6 119.24(12) .
C9 C8 C7 C7 -60.67(18) 2_655
C9 C8 C12 S1 0.64(12) .
C9 C8 C12 C13 176.58(11) .
C8 C9 C10 S1 0.62(13) .
C8 C9 C10 C11 -177.58(12) .
C5 C6 C7 C8 177.94(10) .
C5 C6 C7 C7 -2.15(19) 2_655
C10 S1 C12 C8 -0.25(9) .
C10 S1 C12 C13 -176.60(10) .
C10 C9 C8 C7 172.04(10) .
C10 C9 C8 C12 -0.83(14) .
C7 C6 C5 C4 -178.84(10) .
C7 C6 C5 C5 1.90(19) 2_655
C7 C8 C12 S1 -172.25(9) .
C7 C8 C12 C13 3.69(19) .
C2 C1 C6 C5 -1.92(17) .
C2 C1 C6 C7 -179.73(10) .
C2 C3 C4 C5 -0.58(18) .
C12 S1 C10 C9 -0.21(9) .
C12 S1 C10 C11 178.15(11) .
C12 C8 C7 C6 -68.64(15) .
C12 C8 C7 C7 111.45(15) 2_655
