#------------------------------------------------------------------------------
#$Date: 2020-07-29 04:13:56 +0300 (Wed, 29 Jul 2020) $
#$Revision: 254636 $
#$URL: file:///home/coder/svn-repositories/cod/cif/1/55/86/1558675.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_1558675
loop_
_publ_author_name
'Aitchison, Catherine M.'
'Sachs, Michael'
'Little, Marc'
'Wilbraham, Liam'
'Brownbill, Nick J.'
'Kane, Chris'
'Blanc, Frédéric'
'Zwijnenburg, Martijn'
'Durrant, James'
'Sprick, Reiner Sebastian'
'Cooper, Andrew'
_publ_section_title
;
 Structure-activity relationships in well-defined conjugated oligomer
 photocatalysts for hydrogen production from water
;
_journal_name_full               'Chemical Science'
_journal_paper_doi               10.1039/D0SC02675A
_journal_year                    2020
_chemical_formula_moiety         'C12 H8 O2 S'
_chemical_formula_sum            'C12 H8 O2 S'
_chemical_formula_weight         216.24
_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'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_audit_creation_date             2017-05-15
_audit_creation_method
;
Olex2 1.2
(compiled 2017.03.02 svn.r3394 for OlexSys, GUI svn.r5324)
;
_audit_update_record
;
2020-04-28 deposited with the CCDC.	2020-07-28 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 91.650(2)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   10.1221(8)
_cell_length_b                   13.8377(11)
_cell_length_c                   7.1345(5)
_cell_measurement_reflns_used    3384
_cell_measurement_temperature    298
_cell_measurement_theta_max      28.861
_cell_measurement_theta_min      2.494
_cell_volume                     998.89(13)
_computing_cell_refinement       'SAINT v8.34A (Bruker, 2013)'
_computing_data_collection
;
CrystalClear-SM Expert 2.0 r7 (Rigaku, 2011)
;
_computing_data_reduction        'SAINT v8.34A (Bruker, 2013)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'SIR2004 (Burla et al., 2007)'
_diffrn_ambient_temperature      298.0
_diffrn_detector                 CCD
_diffrn_detector_area_resol_mean 28.5714
_diffrn_detector_type            'Rigaku Saturn724+'
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device       'AFC12 (Right): Kappa 3 circle'
_diffrn_measurement_device_type  'Rigaku Saturn724+ (2x2 bin mode)'
_diffrn_measurement_method       'profile data from ω-scans'
_diffrn_measurement_specimen_support 'Mitegen 50um'
_diffrn_radiation_collimation    0.3
_diffrn_radiation_monochromator  Confocal
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0374
_diffrn_reflns_av_unetI/netI     0.0345
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_l_max       9
_diffrn_reflns_limit_l_min       -6
_diffrn_reflns_number            6680
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         29.152
_diffrn_reflns_theta_min         2.494
_diffrn_source                   'Rotating Anode'
_diffrn_source_current           24.0
_diffrn_source_power             1.2
_diffrn_source_target            Mo
_diffrn_source_type              'Rotating Anode'
_diffrn_source_voltage           50.0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.296
_exptl_absorpt_correction_T_max  0.7458
_exptl_absorpt_correction_T_min  0.4788
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
'SADABS-2014/5 (Bruker,2014/5) was used for absorption correction. wR2(int) was 0.0815 before and 0.0590 after correction. The Ratio of minimum to maximum transmission is 0.6420. The λ/2 correction factor is Not present.'
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.438
_exptl_crystal_description       needle
_exptl_crystal_F_000             448
_exptl_crystal_size_max          0.122
_exptl_crystal_size_mid          0.062
_exptl_crystal_size_min          0.04
_refine_diff_density_max         0.316
_refine_diff_density_min         -0.332
_refine_diff_density_rms         0.045
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.088
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     69
_refine_ls_number_reflns         1349
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.088
_refine_ls_R_factor_all          0.0518
_refine_ls_R_factor_gt           0.0454
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0744P)²+0.3392P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1333
_refine_ls_wR_factor_ref         0.1401
_reflns_Friedel_coverage         0.000
_reflns_number_gt                1139
_reflns_number_total             1349
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d0sc02675a3.cif
_cod_data_source_block           S1_298K_publ
_cod_database_code               1558675
_shelx_shelxl_version_number     2014/7
_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
2.a Aromatic/amide H refined with riding coordinates:
 C2(H2), C3(H3), C4(H4), C5(H5)
;
_shelx_res_file
;
    dibenzothiophene_sulfone_298k.res created by SHELXL-2014/7

TITL Dibenzothiophene_sulfone_298K.res in C2/c
REM Old TITL Dibenzyl_Thiophene_Sulfone_298 in C2/c
REM SHELXT solution in C2/c
REM R1 0.217, Rweak 0.015, Alpha 0.038, Orientation as input
REM Formula found by SHELXT: C14 S
CELL 0.71073 10.1221 13.8377 7.1345 90 91.65 90
ZERR 4 0.0008 0.0011 0.0005 0 0.002 0
LATT 7
SYMM -X,+Y,0.5-Z
SFAC C H O S
UNIT 48 32 8 4

L.S. 20
PLAN  20
TEMP 24.85
BOND $H
list 4
fmap 2
acta
REM <olex2.extras>
REM <HklSrc "%.\\Dibenzothiophene_sulfone_298K.hkl">
REM </olex2.extras>

WGHT    0.074400    0.339200
FVAR       0.87309
S1    4    0.500000    0.296036    0.750000    10.50000    0.05468    0.03816 =
         0.07770    0.00000   -0.01305    0.00000
O1    3    0.521648    0.241760    0.581483    11.00000    0.08123    0.06000 =
         0.11345   -0.03630   -0.01828    0.01383
C1    1    0.623918    0.382577    0.789826    11.00000    0.05149    0.04974 =
         0.04834    0.00167   -0.00471   -0.00522
C2    1    0.755814    0.363857    0.833760    11.00000    0.05347    0.07989 =
         0.06031    0.00820   -0.00719   -0.00298
AFIX  43
H2    2    0.787983    0.300988    0.841536    11.00000   -1.20000
AFIX   0
C3    1    0.837317    0.442527    0.865458    11.00000    0.06046    0.11724 =
         0.06068    0.00767   -0.00713   -0.02946
AFIX  43
H3    2    0.926174    0.432869    0.896679    11.00000   -1.20000
AFIX   0
C4    1    0.788631    0.534557    0.851385    11.00000    0.09182    0.09916 =
         0.05474    0.00033    0.00118   -0.05512
AFIX  43
H4    2    0.845495    0.586423    0.872916    11.00000   -1.20000
AFIX   0
C5    1    0.656391    0.552677    0.805747    11.00000    0.10603    0.05465 =
         0.04984   -0.00162    0.00924   -0.02873
AFIX  43
H5    2    0.625366    0.615809    0.796590    11.00000   -1.20000
AFIX   0
C6    1    0.571378    0.475347    0.774065    11.00000    0.06765    0.04314 =
         0.03863   -0.00054    0.00346   -0.00798
HKLF 4

REM  Dibenzothiophene_sulfone_298K.res in C2/c
REM R1 =  0.0454 for    1139 Fo > 4sig(Fo)  and  0.0518 for all    1349 data
REM     69 parameters refined using      0 restraints

END

WGHT      0.0744      0.3392

REM Highest difference peak  0.316,  deepest hole -0.332,  1-sigma level  0.045
Q1    1   0.5985  0.4255  0.7794  11.00000  0.05    0.32
Q2    1   0.5638  0.3415  0.7759  11.00000  0.05    0.30
Q3    1   0.5000  0.4889  0.7500  10.50000  0.05    0.29
Q4    1   0.6807  0.3799  0.8004  11.00000  0.05    0.25
Q5    1   0.6170  0.5026  0.7838  11.00000  0.05    0.25
Q6    1   0.7557  0.4147  0.8342  11.00000  0.05    0.24
Q7    1   0.7364  0.5679  0.8183  11.00000  0.05    0.22
Q8    1   0.5046  0.2853  0.5557  11.00000  0.05    0.21
Q9    1   0.6015  0.5964  0.7920  11.00000  0.05    0.20
Q10   1   0.5549  0.2680  0.5857  11.00000  0.05    0.19
Q11   1   0.7979  0.4849  0.8217  11.00000  0.05    0.19
Q12   1   0.4735  0.2169  0.6710  11.00000  0.05    0.13
Q13   1   0.8351  0.5384  0.8521  11.00000  0.05    0.10
Q14   1   0.7946  0.6189  0.8726  11.00000  0.05    0.08
Q15   1   0.7641  0.6528  0.8545  11.00000  0.05    0.08
Q16   1   0.5629  0.6395  0.7708  11.00000  0.05    0.08
Q17   1   0.9475  0.3958  0.8839  11.00000  0.05    0.08
Q18   1   0.5833  0.4819  0.5578  11.00000  0.05    0.06
Q19   1   0.9205  0.5421  0.6640  11.00000  0.05    0.06
Q20   1   0.5225  0.4991  0.9691  11.00000  0.05    0.05
;
_shelx_res_checksum              9582
_olex2_submission_special_instructions 'No special instructions were received'
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
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
S1 S 0.5000 0.29604(4) 0.7500 0.0571(2) Uani 1 2 d S T P . .
O1 O 0.52165(16) 0.24176(10) 0.5815(2) 0.0853(5) Uani 1 1 d . . . . .
C1 C 0.62392(15) 0.38258(11) 0.7898(2) 0.0500(4) Uani 1 1 d . . . . .
C2 C 0.75581(18) 0.36386(17) 0.8338(3) 0.0647(5) Uani 1 1 d . . . . .
H2 H 0.7880 0.3010 0.8415 0.078 Uiso 1 1 calc R . . . .
C3 C 0.8373(2) 0.4425(2) 0.8655(3) 0.0796(7) Uani 1 1 d . . . . .
H3 H 0.9262 0.4329 0.8967 0.096 Uiso 1 1 calc R . . . .
C4 C 0.7886(2) 0.5346(2) 0.8514(3) 0.0819(8) Uani 1 1 d . . . . .
H4 H 0.8455 0.5864 0.8729 0.098 Uiso 1 1 calc R . . . .
C5 C 0.6564(2) 0.55268(15) 0.8057(2) 0.0700(6) Uani 1 1 d . . . . .
H5 H 0.6254 0.6158 0.7966 0.084 Uiso 1 1 calc R . . . .
C6 C 0.57138(16) 0.47535(11) 0.7741(2) 0.0498(4) Uani 1 1 d . . . . .
loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
S1 0.0547(4) 0.0382(3) 0.0777(5) 0.000 -0.0131(3) 0.000
O1 0.0812(10) 0.0600(8) 0.1134(12) -0.0363(8) -0.0183(8) 0.0138(7)
C1 0.0515(8) 0.0497(8) 0.0483(8) 0.0017(6) -0.0047(6) -0.0052(6)
C2 0.0535(9) 0.0799(12) 0.0603(10) 0.0082(9) -0.0072(7) -0.0030(8)
C3 0.0605(11) 0.117(2) 0.0607(11) 0.0077(12) -0.0071(8) -0.0295(12)
C4 0.0918(15) 0.0992(17) 0.0547(10) 0.0003(10) 0.0012(9) -0.0551(14)
C5 0.1060(16) 0.0546(9) 0.0498(9) -0.0016(7) 0.0092(9) -0.0287(10)
C6 0.0676(10) 0.0431(7) 0.0386(7) -0.0005(6) 0.0035(6) -0.0080(6)
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'
O O 0.0106 0.0060 '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
_geom_angle_publ_flag
O1 S1 O1 117.11(14) 2_656 . ?
O1 S1 C1 111.51(9) . . ?
O1 S1 C1 111.51(9) 2_656 2_656 ?
O1 S1 C1 110.29(8) 2_656 . ?
O1 S1 C1 110.29(8) . 2_656 ?
C1 S1 C1 93.73(11) . 2_656 ?
C2 C1 S1 126.10(14) . . ?
C2 C1 C6 123.59(16) . . ?
C6 C1 S1 110.31(12) . . ?
C1 C2 H2 121.4 . . ?
C3 C2 C1 117.2(2) . . ?
C3 C2 H2 121.4 . . ?
C2 C3 H3 119.7 . . ?
C4 C3 C2 120.6(2) . . ?
C4 C3 H3 119.7 . . ?
C3 C4 H4 119.1 . . ?
C3 C4 C5 121.80(18) . . ?
C5 C4 H4 119.1 . . ?
C4 C5 H5 120.4 . . ?
C6 C5 C4 119.2(2) . . ?
C6 C5 H5 120.4 . . ?
C1 C6 C6 112.82(9) . 2_656 ?
C5 C6 C1 117.65(17) . . ?
C5 C6 C6 129.53(13) . 2_656 ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
S1 O1 1.4397(15) 2_656 ?
S1 O1 1.4397(15) . ?
S1 C1 1.7515(15) 2_656 ?
S1 C1 1.7515(15) . ?
C1 C2 1.387(2) . ?
C1 C6 1.393(2) . ?
C2 H2 0.9300 . ?
C2 C3 1.381(3) . ?
C3 H3 0.9300 . ?
C3 C4 1.368(4) . ?
C4 H4 0.9300 . ?
C4 C5 1.391(4) . ?
C5 H5 0.9300 . ?
C5 C6 1.388(2) . ?
C6 C6 1.476(3) 2_656 ?
