#------------------------------------------------------------------------------
#$Date: 2022-09-20 11:32:02 +0300 (Tue, 20 Sep 2022) $
#$Revision: 277994 $
#$URL: file:///home/coder/svn-repositories/cod/cif/1/55/86/1558679.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_1558679
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         'C24 H14 O4 S2'
_chemical_formula_sum            'C24 H14 O4 S2'
_chemical_formula_weight         430.47
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2019-11-21
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_audit_update_record
;
2020-04-28 deposited with the CCDC.	2020-07-28 downloaded from the CCDC.
;
_cell_angle_alpha                94.371(5)
_cell_angle_beta                 93.590(6)
_cell_angle_gamma                90.853(5)
_cell_formula_units_Z            2
_cell_length_a                   7.3833(13)
_cell_length_b                   8.4946(16)
_cell_length_c                   15.020(3)
_cell_measurement_reflns_used    2637
_cell_measurement_temperature    298
_cell_measurement_theta_max      25.631
_cell_measurement_theta_min      2.405
_cell_volume                     937.3(3)
_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  'XL (Sheldrick, 2008)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_diffrn_ambient_temperature      298
_diffrn_detector                 CCD
_diffrn_detector_area_resol_mean 28.5714
_diffrn_detector_type            'Rigaku Saturn724+'
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.991
_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_unetI/netI     0.0857
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.991
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -2
_diffrn_reflns_number            3813
_diffrn_reflns_point_group_measured_fraction_full 0.996
_diffrn_reflns_point_group_measured_fraction_max 0.991
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.402
_diffrn_reflns_theta_min         2.405
_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    0.316
_exptl_absorpt_correction_T_max  0.7454
_exptl_absorpt_correction_T_min  0.4827
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
'SADABS-2014/5 (Bruker,2014/5) was used for absorption correction. wR2(int) was 0.0843 before and 0.0668 after correction. The Ratio of minimum to maximum transmission is 0.6476. The λ/2 correction factor is 0.00150.'
_exptl_crystal_colour            'light yellow'
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.525
_exptl_crystal_description       plate
_exptl_crystal_F_000             444
_exptl_crystal_size_max          0.09
_exptl_crystal_size_mid          0.06
_exptl_crystal_size_min          0.01
_refine_diff_density_max         0.306
_refine_diff_density_min         -0.413
_refine_diff_density_rms         0.077
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.057
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     272
_refine_ls_number_reflns         3813
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.057
_refine_ls_R_factor_all          0.1041
_refine_ls_R_factor_gt           0.0653
_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)+(0.0645P)²+0.9621P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1639
_refine_ls_wR_factor_ref         0.1804
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2510
_reflns_number_total             3813
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d0sc02675a3.cif
_cod_data_source_block           s2_298k
_cod_depositor_comments
;

2022-09-17
Z value and formula fixed to values more according to usual
chemical conventions.                 miguel
;
_cod_original_formula_sum            'C48 H28 O8 S4'
_cod_original_formula_weight         860.94
_cod_original_formula_moiety         '2(C24 H14 O4 S2)'
_cod_original_formula_units_Z            1
_cod_database_code               1558679
_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.
;
_shelx_estimated_absorpt_t_max   0.997
_shelx_estimated_absorpt_t_min   0.972
_olex2_refinement_description
;
1. Twinned data refinement
 Scales: 0.802(3)
 0.198(3)
2. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
3.a Aromatic/amide H refined with riding coordinates:
 C2(H2), C4(H4), C5(H5), C9(H9), C10(H10), C11(H11), C12(H12), C14(H14),
 C15(H15), C16(H16), C17(H17), C21(H21), C22(H22), C24(H24)
;
_olex2_submission_special_instructions 'No special instructions were received'
loop_
_space_group_symop_operation_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_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 0.66117(17) 0.54484(11) 0.63924(7) 0.0387(3) Uani 1 1 d . . . . .
S2 S 0.81319(18) -0.09418(13) 0.19538(7) 0.0427(3) Uani 1 1 d . . . . .
O1 O 0.4875(5) 0.4623(3) 0.6326(2) 0.0484(9) Uani 1 1 d . . . . .
O2 O 0.8005(5) 0.4745(4) 0.5875(2) 0.0578(10) Uani 1 1 d . . . . .
O3 O 0.6654(5) -0.2067(4) 0.1934(2) 0.0607(10) Uani 1 1 d . . . . .
O4 O 0.9794(5) -0.1493(4) 0.1589(2) 0.0557(9) Uani 1 1 d . . . . .
C1 C 0.6308(6) 0.7459(4) 0.6217(3) 0.0305(9) Uani 1 1 d . . . . .
C2 C 0.5649(6) 0.8037(4) 0.5431(3) 0.0318(9) Uani 1 1 d . . . . .
H2 H 0.5395 0.7361 0.4920 0.038 Uiso 1 1 calc R . . . .
C3 C 0.5370(5) 0.9659(4) 0.5415(3) 0.0287(9) Uani 1 1 d . . . . .
C4 C 0.5775(6) 1.0606(5) 0.6204(3) 0.0385(11) Uani 1 1 d . . . . .
H4 H 0.5583 1.1686 0.6204 0.046 Uiso 1 1 calc R . . . .
C5 C 0.6455(6) 1.0002(5) 0.6989(3) 0.0371(10) Uani 1 1 d . . . . .
H5 H 0.6721 1.0671 0.7501 0.045 Uiso 1 1 calc R . . . .
C6 C 0.6732(5) 0.8401(4) 0.7002(3) 0.0291(9) Uani 1 1 d . . . . .
C7 C 0.7394(6) 0.5866(5) 0.7520(3) 0.0346(10) Uani 1 1 d . . . . .
C8 C 0.7378(6) 0.7476(4) 0.7747(3) 0.0294(9) Uani 1 1 d . . . . .
C9 C 0.7964(6) 0.8011(5) 0.8621(3) 0.0365(10) Uani 1 1 d . . . . .
H9 H 0.7993 0.9086 0.8795 0.044 Uiso 1 1 calc R . . . .
C10 C 0.8502(6) 0.6932(5) 0.9228(3) 0.0426(11) Uani 1 1 d . . . . .
H10 H 0.8867 0.7288 0.9813 0.051 Uiso 1 1 calc R . . . .
C11 C 0.8504(7) 0.5344(5) 0.8976(3) 0.0447(12) Uani 1 1 d . . . . .
H11 H 0.8901 0.4641 0.9388 0.054 Uiso 1 1 calc R . . . .
C12 C 0.7923(7) 0.4777(5) 0.8118(3) 0.0436(12) Uani 1 1 d . . . . .
H12 H 0.7889 0.3700 0.7949 0.052 Uiso 1 1 calc R . . . .
C13 C 0.7450(6) 0.0816(5) 0.1483(3) 0.0369(10) Uani 1 1 d . . . . .
C14 C 0.6869(7) 0.0960(6) 0.0600(3) 0.0472(12) Uani 1 1 d . . . . .
H14 H 0.6790 0.0085 0.0186 0.057 Uiso 1 1 calc R . . . .
C15 C 0.6412(7) 0.2441(6) 0.0351(3) 0.0510(13) Uani 1 1 d . . . . .
H15 H 0.6004 0.2572 -0.0237 0.061 Uiso 1 1 calc R . . . .
C16 C 0.6558(7) 0.3732(6) 0.0975(3) 0.0468(12) Uani 1 1 d . . . . .
H16 H 0.6254 0.4725 0.0797 0.056 Uiso 1 1 calc R . . . .
C17 C 0.7146(6) 0.3576(5) 0.1856(3) 0.0386(10) Uani 1 1 d . . . . .
H17 H 0.7238 0.4453 0.2268 0.046 Uiso 1 1 calc R . . . .
C18 C 0.7596(6) 0.2090(5) 0.2116(3) 0.0347(10) Uani 1 1 d . . . . .
C19 C 0.8611(6) 0.0043(5) 0.3029(3) 0.0360(10) Uani 1 1 d . . . . .
C20 C 0.8266(6) 0.1646(5) 0.3007(3) 0.0330(9) Uani 1 1 d . . . . .
C21 C 0.8607(6) 0.2592(5) 0.3791(3) 0.0398(11) Uani 1 1 d . . . . .
H21 H 0.8378 0.3667 0.3805 0.048 Uiso 1 1 calc R . . . .
C22 C 0.9293(6) 0.1938(5) 0.4557(3) 0.0412(11) Uani 1 1 d . . . . .
H22 H 0.9541 0.2598 0.5074 0.049 Uiso 1 1 calc R . . . .
C23 C 0.9626(6) 0.0318(5) 0.4583(3) 0.0345(10) Uani 1 1 d . . . . .
C24 C 0.9275(6) -0.0627(5) 0.3788(3) 0.0393(11) Uani 1 1 d . . . . .
H24 H 0.9488 -0.1705 0.3771 0.047 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'
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 C1 110.09(19) . . ?
O1 S1 C7 111.0(2) . . ?
O2 S1 O1 116.4(2) . . ?
O2 S1 C1 112.7(2) . . ?
O2 S1 C7 111.2(2) . . ?
C7 S1 C1 93.00(18) . . ?
O3 S2 O4 117.0(2) . . ?
O3 S2 C13 111.6(2) . . ?
O3 S2 C19 112.7(2) . . ?
O4 S2 C13 110.3(2) . . ?
O4 S2 C19 109.9(2) . . ?
C13 S2 C19 92.6(2) . . ?
C2 C1 S1 125.5(3) . . ?
C2 C1 C6 123.7(3) . . ?
C6 C1 S1 110.7(3) . . ?
C1 C2 H2 120.6 . . ?
C1 C2 C3 118.7(3) . . ?
C3 C2 H2 120.6 . . ?
C2 C3 C3 120.8(4) . 2_676 ?
C4 C3 C2 117.7(4) . . ?
C4 C3 C3 121.4(4) . 2_676 ?
C3 C4 H4 118.7 . . ?
C5 C4 C3 122.7(4) . . ?
C5 C4 H4 118.7 . . ?
C4 C5 H5 120.3 . . ?
C6 C5 C4 119.4(4) . . ?
C6 C5 H5 120.3 . . ?
C1 C6 C8 112.5(3) . . ?
C5 C6 C1 117.7(4) . . ?
C5 C6 C8 129.8(4) . . ?
C8 C7 S1 110.3(3) . . ?
C12 C7 S1 126.4(3) . . ?
C12 C7 C8 123.2(4) . . ?
C7 C8 C6 113.5(3) . . ?
C7 C8 C9 117.7(4) . . ?
C9 C8 C6 128.8(4) . . ?
C8 C9 H9 120.2 . . ?
C10 C9 C8 119.7(4) . . ?
C10 C9 H9 120.2 . . ?
C9 C10 H10 119.6 . . ?
C11 C10 C9 120.8(4) . . ?
C11 C10 H10 119.6 . . ?
C10 C11 H11 119.6 . . ?
C10 C11 C12 120.8(4) . . ?
C12 C11 H11 119.6 . . ?
C7 C12 H12 121.2 . . ?
C11 C12 C7 117.7(4) . . ?
C11 C12 H12 121.2 . . ?
C14 C13 S2 126.2(4) . . ?
C18 C13 S2 111.1(3) . . ?
C18 C13 C14 122.7(4) . . ?
C13 C14 H14 121.0 . . ?
C15 C14 C13 118.0(4) . . ?
C15 C14 H14 121.0 . . ?
C14 C15 H15 119.9 . . ?
C14 C15 C16 120.1(4) . . ?
C16 C15 H15 119.9 . . ?
C15 C16 H16 119.3 . . ?
C17 C16 C15 121.4(4) . . ?
C17 C16 H16 119.3 . . ?
C16 C17 H17 120.5 . . ?
C16 C17 C18 119.0(4) . . ?
C18 C17 H17 120.5 . . ?
C13 C18 C17 118.8(4) . . ?
C13 C18 C20 112.7(4) . . ?
C17 C18 C20 128.5(4) . . ?
C20 C19 S2 110.2(3) . . ?
C24 C19 S2 126.6(3) . . ?
C24 C19 C20 123.2(4) . . ?
C19 C20 C18 113.3(4) . . ?
C21 C20 C18 129.1(4) . . ?
C21 C20 C19 117.6(4) . . ?
C20 C21 H21 120.0 . . ?
C20 C21 C22 119.9(4) . . ?
C22 C21 H21 120.0 . . ?
C21 C22 H22 118.7 . . ?
C21 C22 C23 122.6(4) . . ?
C23 C22 H22 118.7 . . ?
C22 C23 C23 120.4(4) . 2_756 ?
C24 C23 C22 117.0(4) . . ?
C24 C23 C23 122.5(5) . 2_756 ?
C19 C24 C23 119.7(4) . . ?
C19 C24 H24 120.1 . . ?
C23 C24 H24 120.1 . . ?
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 1.446(3) . ?
S1 O2 1.438(3) . ?
S1 C1 1.763(4) . ?
S1 C7 1.763(4) . ?
S2 O3 1.437(4) . ?
S2 O4 1.445(4) . ?
S2 C13 1.767(4) . ?
S2 C19 1.774(4) . ?
C1 C2 1.377(5) . ?
C1 C6 1.390(5) . ?
C2 H2 0.9300 . ?
C2 C3 1.398(5) . ?
C3 C3 1.490(8) 2_676 ?
C3 C4 1.394(5) . ?
C4 H4 0.9300 . ?
C4 C5 1.390(6) . ?
C5 H5 0.9300 . ?
C5 C6 1.380(5) . ?
C6 C8 1.475(5) . ?
C7 C8 1.384(5) . ?
C7 C12 1.382(6) . ?
C8 C9 1.395(6) . ?
C9 H9 0.9300 . ?
C9 C10 1.387(6) . ?
C10 H10 0.9300 . ?
C10 C11 1.373(6) . ?
C11 H11 0.9300 . ?
C11 C12 1.380(6) . ?
C12 H12 0.9300 . ?
C13 C14 1.383(6) . ?
C13 C18 1.384(6) . ?
C14 H14 0.9300 . ?
C14 C15 1.380(7) . ?
C15 H15 0.9300 . ?
C15 C16 1.386(7) . ?
C16 H16 0.9300 . ?
C16 C17 1.384(6) . ?
C17 H17 0.9300 . ?
C17 C18 1.388(6) . ?
C18 C20 1.476(6) . ?
C19 C20 1.392(6) . ?
C19 C24 1.379(6) . ?
C20 C21 1.381(6) . ?
C21 H21 0.9300 . ?
C21 C22 1.386(6) . ?
C22 H22 0.9300 . ?
C22 C23 1.405(6) . ?
C23 C23 1.481(8) 2_756 ?
C23 C24 1.395(6) . ?
C24 H24 0.9300 . ?
loop_
_twin_individual_id
_twin_individual_mass_fraction_refined
1 0.802(3)
2 0.198(3)
