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#$Date: 2024-08-05 20:24:12 +0300 (Mon, 05 Aug 2024) $
#$Revision: 293689 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/13/33/7133362.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_7133362
loop_
_publ_author_name
'Reid, Amelia G.'
'Zelenke, Ethan A.'
'Moberg, Megan E.'
'Dickie, Diane A.'
'Machan, Charles W.'
_publ_section_title
;
 Improving co-electrocatalytic carbon dioxide reduction by optimizing the
 relative potentials of the redox mediator and catalyst.
;
_journal_issue                   63
_journal_name_full               'Chemical communications (Cambridge, England)'
_journal_page_first              8208
_journal_page_last               8211
_journal_paper_doi               10.1039/d4cc01988a
_journal_volume                  60
_journal_year                    2024
_chemical_formula_sum            'C16 H10 O2 S'
_chemical_formula_weight         266.30
_chemical_name_common            BNTD
_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_update_record
;
2024-04-24 deposited with the CCDC.	2024-07-09 downloaded from the CCDC.
;
_cell_angle_alpha                111.229(2)
_cell_angle_beta                 102.154(2)
_cell_angle_gamma                93.290(2)
_cell_formula_units_Z            2
_cell_length_a                   7.6112(4)
_cell_length_b                   8.5345(5)
_cell_length_c                   9.9571(6)
_cell_measurement_reflns_used    7590
_cell_measurement_temperature    100.(2)
_cell_measurement_theta_max      27.4683
_cell_measurement_theta_min      2.2656
_cell_volume                     583.02(6)
_computing_cell_refinement       'SAINT V8.40B (Bruker AXS LLC, 2019)'
_computing_data_collection       'Bruker Instrument Service v8.5.0.27'
_computing_data_reduction        'SAINT V8.40B (Bruker AXS LLC, 2019)'
_computing_structure_refinement  'SHELXL-2019/1 (Sheldrick, 2019)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_diffrn_ambient_temperature      100.(2)
_diffrn_detector_area_resol_mean 7.3910
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_device       'Kappa four-circle diffractometer'
_diffrn_measurement_device_type  'Bruker D8 Venture'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_monochromator  'HELIOS double bounce multilayer mirror'
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0457
_diffrn_reflns_av_unetI/netI     0.0326
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            16732
_diffrn_reflns_theta_full        25.24
_diffrn_reflns_theta_max         27.48
_diffrn_reflns_theta_min         2.27
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_current           1.4
_diffrn_source_power             0.07
_diffrn_source_type              'Incoatec I\mS 3.0'
_diffrn_source_voltage           50
_exptl_absorpt_coefficient_mu    0.270
_exptl_absorpt_correction_T_max  0.98
_exptl_absorpt_correction_T_min  0.90
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
Krause, L., Herbst-Irmer, R., Sheldrick, G. M., Stalke, D. (2015).
"Comparison of silver and molybdenum microfocus X-ray sources for
single-crystal structure determination"
J. Appl. Cryst. 48, 3-10.
doi:10.1107/S1600576714022985
;
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.517
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             276
_exptl_crystal_size_max          0.158
_exptl_crystal_size_mid          0.127
_exptl_crystal_size_min          0.081
_refine_diff_density_max         0.434
_refine_diff_density_min         -0.368
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.075
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     172
_refine_ls_number_reflns         2657
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.075
_refine_ls_R_factor_all          0.0452
_refine_ls_R_factor_gt           0.0399
_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)+(0.0509P)²+0.4148P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1051
_refine_ls_wR_factor_ref         0.1089
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2350
_reflns_number_total             2657
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d4cc01988a2.cif
_cod_data_source_block           BNTD
_cod_depositor_comments
;
The following automatic conversions were performed:

data item '_exptl_absorpt_correction_type' value 'Multi-Scan' was
changed to 'multi-scan' in accordance with the
/home/data/users/saulius/crontab/automatic-downloads/rss-feeds/RSC/lib/dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.2 last updated on
2011-04-26.

Automatic conversion script
Id: cif_fix_values 8170 2020-07-09 18:12:32Z antanas 

 Adding full bibliography for 7133362.cif.
;
_cod_database_code               7133362
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'
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_adp
_atom_site_refinement_flags_occupancy
_atom_site_refinement_flags_posn
_atom_site_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
S S1 0.09697(6) 0.73223(5) 0.31613(5) 0.01980(14) Uani d . . . 1 . .
O O1 -0.06620(17) 0.80604(16) 0.33438(15) 0.0277(3) Uani d . . . 1 . .
O O2 0.19326(18) 0.77703(16) 0.22180(14) 0.0256(3) Uani d . . . 1 . .
C C1 0.0558(2) 0.5118(2) 0.26640(19) 0.0187(3) Uani d . . . 1 . .
C C2 -0.0539(2) 0.3986(2) 0.13312(19) 0.0206(3) Uani d . . . 1 . .
H H2 -0.113628 0.436511 0.059174 0.025000 Uiso calc U . R 1 . .
C C3 -0.0742(2) 0.2273(2) 0.11043(19) 0.0225(4) Uani d . . . 1 . .
H H3 -0.146329 0.145521 0.019001 0.027000 Uiso calc U . R 1 . .
C C4 0.0113(2) 0.1764(2) 0.2221(2) 0.0229(4) Uani d . . . 1 . .
H H4 -0.005582 0.059503 0.206734 0.027000 Uiso calc U . R 1 . .
C C5 0.1212(2) 0.2925(2) 0.35594(19) 0.0210(3) Uani d . . . 1 . .
H H5 0.178124 0.254467 0.430659 0.025000 Uiso calc U . R 1 . .
C C6 0.1478(2) 0.4651(2) 0.38056(18) 0.0178(3) Uani d . . . 1 . .
C C7 0.2593(2) 0.6143(2) 0.50978(18) 0.0173(3) Uani d . . . 1 . .
C C8 0.3753(2) 0.6235(2) 0.64670(18) 0.0185(3) Uani d . . . 1 . .
C C9 0.4067(2) 0.4817(2) 0.68590(19) 0.0219(3) Uani d . . . 1 . .
H H9 0.349332 0.371295 0.617990 0.026000 Uiso calc U . R 1 . .
C C10 0.5186(2) 0.5009(2) 0.8202(2) 0.0250(4) Uani d . . . 1 . .
H H10 0.537733 0.403798 0.843580 0.030000 Uiso calc U . R 1 . .
C C11 0.6049(2) 0.6622(3) 0.9233(2) 0.0262(4) Uani d . . . 1 . .
H H11 0.681039 0.674081 1.016273 0.031000 Uiso calc U . R 1 . .
C C12 0.5792(2) 0.8017(2) 0.8894(2) 0.0245(4) Uani d . . . 1 . .
H H12 0.638113 0.910602 0.959572 0.029000 Uiso calc U . R 1 . .
C C13 0.4661(2) 0.7873(2) 0.75148(19) 0.0208(3) Uani d . . . 1 . .
C C14 0.4447(2) 0.9346(2) 0.7188(2) 0.0233(4) Uani d . . . 1 . .
H H14 0.507914 1.041696 0.789281 0.028000 Uiso calc U . R 1 . .
C C15 0.3353(2) 0.9253(2) 0.5884(2) 0.0225(4) Uani d . . . 1 . .
H H15 0.321097 1.023785 0.566135 0.027000 Uiso calc U . R 1 . .
C C16 0.2444(2) 0.7647(2) 0.48814(18) 0.0188(3) Uani d . . . 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'
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_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle
_geom_angle_publ_flag
O1 S1 O2 . . 116.38(8) ?
O1 S1 C1 . . 110.63(8) ?
O2 S1 C1 . . 112.16(8) ?
O1 S1 C16 . . 111.64(8) ?
O2 S1 C16 . . 110.85(8) ?
C1 S1 C16 . . 92.77(8) ?
C2 C1 C6 . . 124.17(16) ?
C2 C1 S1 . . 124.68(13) ?
C6 C1 S1 . . 111.15(12) ?
C1 C2 C3 . . 117.93(16) ?
C1 C2 H2 . . 121.000000 ?
C3 C2 H2 . . 121.000000 ?
C4 C3 C2 . . 119.63(16) ?
C4 C3 H3 . . 120.200000 ?
C2 C3 H3 . . 120.200000 ?
C3 C4 C5 . . 121.61(16) ?
C3 C4 H4 . . 119.200000 ?
C5 C4 H4 . . 119.200000 ?
C4 C5 C6 . . 120.06(16) ?
C4 C5 H5 . . 120.000000 ?
C6 C5 H5 . . 120.000000 ?
C5 C6 C1 . . 116.56(15) ?
C5 C6 C7 . . 131.35(15) ?
C1 C6 C7 . . 112.08(14) ?
C16 C7 C8 . . 117.40(15) ?
C16 C7 C6 . . 112.10(14) ?
C8 C7 C6 . . 130.50(15) ?
C9 C8 C13 . . 117.57(15) ?
C9 C8 C7 . . 124.58(15) ?
C13 C8 C7 . . 117.84(15) ?
C10 C9 C8 . . 121.21(17) ?
C10 C9 H9 . . 119.400000 ?
C8 C9 H9 . . 119.400000 ?
C9 C10 C11 . . 120.89(17) ?
C9 C10 H10 . . 119.600000 ?
C11 C10 H10 . . 119.600000 ?
C12 C11 C10 . . 119.72(17) ?
C12 C11 H11 . . 120.100000 ?
C10 C11 H11 . . 120.100000 ?
C11 C12 C13 . . 121.20(17) ?
C11 C12 H12 . . 119.400000 ?
C13 C12 H12 . . 119.400000 ?
C12 C13 C14 . . 119.77(16) ?
C12 C13 C8 . . 119.40(16) ?
C14 C13 C8 . . 120.84(16) ?
C15 C14 C13 . . 121.19(16) ?
C15 C14 H14 . . 119.400000 ?
C13 C14 H14 . . 119.400000 ?
C14 C15 C16 . . 117.36(16) ?
C14 C15 H15 . . 121.300000 ?
C16 C15 H15 . . 121.300000 ?
C7 C16 C15 . . 125.35(16) ?
C7 C16 S1 . . 111.85(12) ?
C15 C16 S1 . . 122.80(13) ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_site_symmetry_2
_geom_bond_distance
_geom_bond_publ_flag
S1 O1 . 1.4402(13) ?
S1 O2 . 1.4434(13) ?
S1 C1 . 1.7539(17) ?
S1 C16 . 1.7550(17) ?
C1 C2 . 1.380(2) ?
C1 C6 . 1.402(2) ?
C2 C3 . 1.390(2) ?
C2 H2 . 0.950000 ?
C3 C4 . 1.387(3) ?
C3 H3 . 0.950000 ?
C4 C5 . 1.392(2) ?
C4 H4 . 0.950000 ?
C5 C6 . 1.397(2) ?
C5 H5 . 0.950000 ?
C6 C7 . 1.492(2) ?
C7 C16 . 1.384(2) ?
C7 C8 . 1.432(2) ?
C8 C9 . 1.418(2) ?
C8 C13 . 1.431(2) ?
C9 C10 . 1.373(2) ?
C9 H9 . 0.950000 ?
C10 C11 . 1.403(3) ?
C10 H10 . 0.950000 ?
C11 C12 . 1.364(3) ?
C11 H11 . 0.950000 ?
C12 C13 . 1.418(2) ?
C12 H12 . 0.950000 ?
C13 C14 . 1.418(2) ?
C14 C15 . 1.359(3) ?
C14 H14 . 0.950000 ?
C15 C16 . 1.401(2) ?
C15 H15 . 0.950000 ?
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_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion
_geom_torsion_publ_flag
O1 S1 C1 C2 . . . . 66.97(16) ?
O2 S1 C1 C2 . . . . -64.78(17) ?
C16 S1 C1 C2 . . . . -178.65(15) ?
O1 S1 C1 C6 . . . . -112.46(13) ?
O2 S1 C1 C6 . . . . 115.78(12) ?
C16 S1 C1 C6 . . . . 1.92(13) ?
C6 C1 C2 C3 . . . . -0.1(3) ?
S1 C1 C2 C3 . . . . -179.51(12) ?
C1 C2 C3 C4 . . . . 1.6(2) ?
C2 C3 C4 C5 . . . . -1.5(3) ?
C3 C4 C5 C6 . . . . -0.1(3) ?
C4 C5 C6 C1 . . . . 1.4(2) ?
C4 C5 C6 C7 . . . . -178.59(16) ?
C2 C1 C6 C5 . . . . -1.4(2) ?
S1 C1 C6 C5 . . . . 178.09(12) ?
C2 C1 C6 C7 . . . . 178.66(15) ?
S1 C1 C6 C7 . . . . -1.90(17) ?
C5 C6 C7 C16 . . . . -179.13(16) ?
C1 C6 C7 C16 . . . . 0.86(19) ?
C5 C6 C7 C8 . . . . 1.2(3) ?
C1 C6 C7 C8 . . . . -178.82(16) ?
C16 C7 C8 C9 . . . . -179.51(15) ?
C6 C7 C8 C9 . . . . 0.2(3) ?
C16 C7 C8 C13 . . . . 0.4(2) ?
C6 C7 C8 C13 . . . . -179.92(15) ?
C13 C8 C9 C10 . . . . 0.7(2) ?
C7 C8 C9 C10 . . . . -179.34(15) ?
C8 C9 C10 C11 . . . . 0.2(3) ?
C9 C10 C11 C12 . . . . -0.7(3) ?
C10 C11 C12 C13 . . . . 0.1(3) ?
C11 C12 C13 C14 . . . . -178.95(16) ?
C11 C12 C13 C8 . . . . 0.9(3) ?
C9 C8 C13 C12 . . . . -1.3(2) ?
C7 C8 C13 C12 . . . . 178.78(15) ?
C9 C8 C13 C14 . . . . 178.56(15) ?
C7 C8 C13 C14 . . . . -1.4(2) ?
C12 C13 C14 C15 . . . . -179.09(16) ?
C8 C13 C14 C15 . . . . 1.1(3) ?
C13 C14 C15 C16 . . . . 0.2(2) ?
C8 C7 C16 C15 . . . . 0.9(2) ?
C6 C7 C16 C15 . . . . -178.81(15) ?
C8 C7 C16 S1 . . . . -179.68(11) ?
C6 C7 C16 S1 . . . . 0.59(17) ?
C14 C15 C16 C7 . . . . -1.2(3) ?
C14 C15 C16 S1 . . . . 179.41(13) ?
O1 S1 C16 C7 . . . . 112.06(13) ?
O2 S1 C16 C7 . . . . -116.43(12) ?
C1 S1 C16 C7 . . . . -1.43(13) ?
O1 S1 C16 C15 . . . . -68.51(16) ?
O2 S1 C16 C15 . . . . 62.99(16) ?
C1 S1 C16 C15 . . . . 177.99(14) ?
