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#$Date: 2023-05-05 05:51:00 +0300 (Fri, 05 May 2023) $
#$Revision: 283372 $
#$URL: file:///home/coder/svn-repositories/cod/cif/1/56/84/1568462.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_1568462
loop_
_publ_author_name
'Mang, André'
'Rotthowe, Nils'
'Beltako, Katawoura'
'Linseis, Michael'
'Pauly, Fabian'
'Winter, Rainer F.'
_publ_section_title
;
 Single-molecule conductance studies on quasi- and metallaaromatic
 dibenzoylmethane coordination compounds and their aromatic analogs.
;
_journal_issue                   11
_journal_name_full               Nanoscale
_journal_page_first              5305
_journal_page_last               5316
_journal_paper_doi               10.1039/d2nr05670d
_journal_volume                  15
_journal_year                    2023
_chemical_formula_moiety         'C25 H27 O2 Rh S2'
_chemical_formula_sum            'C25 H27 O2 Rh S2'
_chemical_formula_weight         526.49
_space_group_crystal_system      orthorhombic
_space_group_IT_number           62
_space_group_name_Hall           '-P 2ac 2n'
_space_group_name_H-M_alt        'P n m a'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2022-03-22
_audit_creation_method
;
Olex2 1.5
(compiled 2021.12.09 svn.r5202d8cf for OlexSys, GUI svn.r6439)
;
_audit_update_record
;
2022-03-24 deposited with the CCDC.	2023-02-14 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   9.4517(3)
_cell_length_b                   23.2662(4)
_cell_length_c                   10.4808(7)
_cell_measurement_reflns_used    15216
_cell_measurement_temperature    100
_cell_measurement_theta_max      27.99
_cell_measurement_theta_min      2.90
_cell_volume                     2304.78(17)
_computing_cell_refinement
;
X-Area Recipe 1.33.0.0 (STOE, 2015)
;
_computing_data_collection
;
X-Area WinXpose 2.0.22.0 (STOE, 2016)
;
_computing_data_reduction
;
X-Area Integrate 1.74.2.0 (STOE, 2018)
X-Area LANA 1.75.3.0 (STOE, 2018)
;
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_diffrn_ambient_temperature      100.00
_diffrn_detector_area_resol_mean 6.67
_diffrn_detector_type            'STOE Imaging Plate'
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.992
_diffrn_measurement_details
;
 128 frames, detector distance = 100 mm
;
_diffrn_measurement_device       '2-circle diffractometer'
_diffrn_measurement_device_type  'STOE IPDS 2T'
_diffrn_measurement_method       'rotation method, ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0279
_diffrn_reflns_av_unetI/netI     0.0211
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.992
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       30
_diffrn_reflns_limit_k_min       -25
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            10632
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.992
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.597
_diffrn_reflns_theta_min         2.131
_exptl_absorpt_coefficient_mu    0.941
_exptl_absorpt_correction_T_max  0.8698
_exptl_absorpt_correction_T_min  0.6420
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
STOE LANA, absorption correction by scaling of reflection intensities.
J. Koziskova, F. Hahn, J. Richter, J. Kozisek, "Comparison of different
absorption corrections on the model structure of tetrakis(μ₂-acetato)-
diaqua-di-copper(II)", Acta Chimica Slovaca, vol. 9, no. 2, 2016, pp. 136 - 140.
Afterwards a spherical absorption correction was performed within STOE LANA.
;
_exptl_crystal_colour            yellow
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.517
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       needle
_exptl_crystal_F_000             1080
_exptl_crystal_recrystallization_method 'Re-crystallisation from solvent'
_exptl_crystal_size_max          0.3
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.1
_refine_diff_density_max         0.329
_refine_diff_density_min         -0.671
_refine_diff_density_rms         0.079
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.154
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     172
_refine_ls_number_reflns         2723
_refine_ls_number_restraints     28
_refine_ls_restrained_S_all      1.149
_refine_ls_R_factor_all          0.0417
_refine_ls_R_factor_gt           0.0325
_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)+(0.0129P)²+5.0662P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0643
_refine_ls_wR_factor_ref         0.0674
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2384
_reflns_number_total             2723
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d2nr05670d2.cif
_cod_data_source_block           am010
_cod_depositor_comments
'Adding full bibliography for 1568461--1568464.cif.'
_cod_database_code               1568462
_shelx_shelxl_version_number     2018/3
_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.
;
_shelx_estimated_absorpt_t_max   0.912
_shelx_estimated_absorpt_t_min   0.765
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
2. Restrained distances
 C11-C10 \\sim C13-C12
 with sigma of 0.01
 C16-C17 \\sim C14-C15
 with sigma of 0.01
 C17-C10 \\sim C14-C13
 with sigma of 0.01
 C12-C11 \\sim C15-C16
 with sigma of 0.01
3. Uiso/Uaniso restraints and constraints
Uanis(C10) \\sim Ueq, Uanis(C17) \\sim Ueq, Uanis(C13) \\sim Ueq, Uanis(C14)
\\sim Ueq: with sigma of 0.01 and sigma for terminal atoms of 0.02
Uanis(C14) = Uanis(C17)
Uanis(C10) = Uanis(C13)
4. Others
 Fixed Sof: C10(0.5) H10(0.5) C17(0.5) H17(0.5) C11(0.5) H11A(0.5) H11B(0.5)
 C16(0.5) H16A(0.5) H16B(0.5) C12(0.5) H12A(0.5) H12B(0.5) C15(0.5) H15A(0.5)
 H15B(0.5) C13(0.5) H13(0.5) C14(0.5) H14(0.5)
5.a Ternary CH refined with riding coordinates:
 C10(H10), C17(H17), C13(H13), C14(H14)
5.b Secondary CH2 refined with riding coordinates:
 C11(H11A,H11B), C16(H16A,H16B), C12(H12A,H12B), C15(H15A,H15B)
5.c Aromatic/amide H refined with riding coordinates:
 C4(H4), C3(H3), C6(H6), C9(H9), C7(H7)
5.d Idealised Me refined as rotating group:
 C1(H1A,H1B,H1C)
;
_olex2_submission_special_instructions 'No special instructions were received'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'x+1/2, -y+1/2, -z+1/2'
'-x, y+1/2, -z'
'-x, -y, -z'
'x-1/2, y, -z-1/2'
'-x-1/2, y-1/2, z-1/2'
'x, -y-1/2, 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
Rh1 Rh 0.44750(3) 0.250000 0.52713(3) 0.01639(8) Uani 1 2 d S T P . .
S1 S 0.99552(9) 0.52507(3) 0.26544(8) 0.03313(18) Uani 1 1 d . . . . .
O1 O 0.58330(17) 0.31253(8) 0.46791(18) 0.0199(4) Uani 1 1 d . . . . .
C8 C 0.7047(3) 0.30390(11) 0.4168(2) 0.0169(5) Uani 1 1 d . . . . .
C5 C 0.7832(3) 0.35724(11) 0.3857(2) 0.0174(5) Uani 1 1 d . . . . .
C4 C 0.7520(3) 0.40793(11) 0.4509(2) 0.0207(5) Uani 1 1 d . . . . .
H4 H 0.685507 0.407021 0.518757 0.023(8) Uiso 1 1 calc R . . . .
C3 C 0.8155(3) 0.45940(12) 0.4191(3) 0.0240(6) Uani 1 1 d . . . . .
H3 H 0.793119 0.493268 0.465596 0.033(9) Uiso 1 1 calc R . . . .
C10 C 0.2728(15) 0.3092(5) 0.5304(12) 0.0212(11) Uani 0.5 1 d D U P A -1
H10 H 0.284313 0.346201 0.482896 0.025 Uiso 0.5 1 calc R U P A -1
C6 C 0.8840(3) 0.35956(11) 0.2880(2) 0.0202(5) Uani 1 1 d . . . . .
H6 H 0.909886 0.325393 0.244243 0.021(7) Uiso 1 1 calc R . . . .
C17 C 0.3389(14) 0.3047(9) 0.6487(9) 0.0173(15) Uani 0.5 1 d D U P A -1
H17 H 0.393796 0.339665 0.673623 0.021 Uiso 0.5 1 calc R U P A -1
C9 C 0.7640(4) 0.250000 0.3906(3) 0.0183(7) Uani 1 2 d S T P . .
H9 H 0.854292 0.250000 0.350791 0.007(8) Uiso 1 2 calc R . P . .
C2 C 0.9125(3) 0.46175(11) 0.3188(3) 0.0232(6) Uani 1 1 d . . . . .
C7 C 0.9459(3) 0.41110(11) 0.2549(3) 0.0239(5) Uani 1 1 d . . . . .
H7 H 1.012588 0.412057 0.187089 0.034(9) Uiso 1 1 calc R . . . .
C1 C 0.9067(3) 0.58023(12) 0.3546(3) 0.0358(7) Uani 1 1 d . . . . .
H1A H 0.940227 0.618019 0.326556 0.048(10) Uiso 1 1 calc R . . . .
H1B H 0.926815 0.575354 0.445712 0.051(11) Uiso 1 1 calc R . . . .
H1C H 0.804430 0.577404 0.340294 0.043(10) Uiso 1 1 calc R . . . .
C11 C 0.1321(9) 0.2790(4) 0.5199(7) 0.0201(16) Uani 0.5 1 d D . P A -1
H11A H 0.070913 0.299962 0.458882 0.024 Uiso 0.5 1 calc R U P A -1
H11B H 0.084660 0.279098 0.604062 0.024 Uiso 0.5 1 calc R U P A -1
C16 C 0.2647(10) 0.2756(4) 0.7594(8) 0.0235(19) Uani 0.5 1 d D . P A -1
H16A H 0.161042 0.278460 0.747624 0.028 Uiso 0.5 1 calc R U P A -1
H16B H 0.289616 0.295544 0.839798 0.028 Uiso 0.5 1 calc R U P A -1
C12 C 0.1516(10) 0.2170(5) 0.4744(7) 0.0234(18) Uani 0.5 1 d D . P A -1
H12A H 0.069700 0.193787 0.502874 0.028 Uiso 0.5 1 calc R U P A -1
H12B H 0.153297 0.216392 0.379984 0.028 Uiso 0.5 1 calc R U P A -1
C15 C 0.3077(9) 0.2123(5) 0.7685(8) 0.025(2) Uani 0.5 1 d D . P A -1
H15A H 0.387482 0.208962 0.829253 0.029 Uiso 0.5 1 calc R U P A -1
H15B H 0.227248 0.190312 0.804323 0.029 Uiso 0.5 1 calc R U P A -1
C13 C 0.2862(16) 0.1899(6) 0.5243(12) 0.0212(11) Uani 0.5 1 d D U P A -1
H13 H 0.313696 0.156772 0.468865 0.025 Uiso 0.5 1 calc R U P A -1
C14 C 0.3511(15) 0.1847(9) 0.6429(9) 0.0173(15) Uani 0.5 1 d D U P A -1
H14 H 0.409708 0.149209 0.652795 0.021 Uiso 0.5 1 calc R U P 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'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Rh Rh -1.1178 0.9187 '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 Rh1 O1 91.16(10) 8_565 . ?
O1 Rh1 C10 161.1(3) 8_565 . ?
O1 Rh1 C10 91.8(3) . . ?
O1 Rh1 C17 93.5(3) . . ?
O1 Rh1 C17 159.7(3) 8_565 . ?
O1 Rh1 C13 88.7(3) 8_565 . ?
O1 Rh1 C13 160.5(3) . . ?
O1 Rh1 C14 160.9(3) . . ?
O1 Rh1 C14 86.2(2) 8_565 . ?
C17 Rh1 C10 38.4(3) . . ?
C17 Rh1 C14 82.9(2) . . ?
C13 Rh1 C10 82.39(17) . . ?
C13 Rh1 C17 93.4(5) . . ?
C13 Rh1 C14 38.5(3) . . ?
C14 Rh1 C10 96.8(4) . . ?
C2 S1 C1 102.96(14) . . ?
C8 O1 Rh1 125.42(17) . . ?
O1 C8 C5 114.1(2) . . ?
O1 C8 C9 125.4(3) . . ?
C9 C8 C5 120.5(2) . . ?
C4 C5 C8 119.7(2) . . ?
C4 C5 C6 118.0(2) . . ?
C6 C5 C8 122.2(2) . . ?
C5 C4 H4 119.2 . . ?
C3 C4 C5 121.6(2) . . ?
C3 C4 H4 119.2 . . ?
C4 C3 H3 120.0 . . ?
C4 C3 C2 120.0(3) . . ?
C2 C3 H3 120.0 . . ?
Rh1 C10 H10 117.4 . . ?
C17 C10 Rh1 67.7(11) . . ?
C17 C10 H10 117.4 . . ?
C17 C10 C11 115.2(11) . . ?
C11 C10 Rh1 112.2(8) . . ?
C11 C10 H10 117.4 . . ?
C5 C6 H6 119.8 . . ?
C7 C6 C5 120.5(2) . . ?
C7 C6 H6 119.8 . . ?
Rh1 C17 H17 113.8 . . ?
C10 C17 Rh1 73.8(10) . . ?
C10 C17 H17 113.8 . . ?
C10 C17 C16 120.5(9) . . ?
C16 C17 Rh1 115.2(12) . . ?
C16 C17 H17 113.8 . . ?
C8 C9 C8 127.1(3) . 8_565 ?
C8 C9 H9 116.4 . . ?
C8 C9 H9 116.4 8_565 . ?
C3 C2 S1 124.4(2) . . ?
C7 C2 S1 117.1(2) . . ?
C7 C2 C3 118.6(2) . . ?
C6 C7 C2 121.3(2) . . ?
C6 C7 H7 119.4 . . ?
C2 C7 H7 119.4 . . ?
S1 C1 H1A 109.5 . . ?
S1 C1 H1B 109.5 . . ?
S1 C1 H1C 109.5 . . ?
H1A C1 H1B 109.5 . . ?
H1A C1 H1C 109.5 . . ?
H1B C1 H1C 109.5 . . ?
C10 C11 H11A 109.5 . . ?
C10 C11 H11B 109.5 . . ?
C10 C11 C12 110.8(9) . . ?
H11A C11 H11B 108.1 . . ?
C12 C11 H11A 109.5 . . ?
C12 C11 H11B 109.5 . . ?
C17 C16 H16A 109.5 . . ?
C17 C16 H16B 109.5 . . ?
C17 C16 C15 110.8(13) . . ?
H16A C16 H16B 108.1 . . ?
C15 C16 H16A 109.5 . . ?
C15 C16 H16B 109.5 . . ?
C11 C12 H12A 109.0 . . ?
C11 C12 H12B 109.0 . . ?
H12A C12 H12B 107.8 . . ?
C13 C12 C11 112.7(10) . . ?
C13 C12 H12A 109.0 . . ?
C13 C12 H12B 109.0 . . ?
C16 C15 H15A 108.5 . . ?
C16 C15 H15B 108.5 . . ?
H15A C15 H15B 107.5 . . ?
C14 C15 C16 115.0(11) . . ?
C14 C15 H15A 108.5 . . ?
C14 C15 H15B 108.5 . . ?
Rh1 C13 H13 109.8 . . ?
C12 C13 Rh1 110.1(8) . . ?
C12 C13 H13 109.8 . . ?
C14 C13 Rh1 73.8(11) . . ?
C14 C13 C12 135.7(12) . . ?
C14 C13 H13 109.8 . . ?
Rh1 C14 H14 114.1 . . ?
C15 C14 Rh1 107.8(12) . . ?
C15 C14 H14 114.1 . . ?
C13 C14 Rh1 67.7(11) . . ?
C13 C14 C15 128.1(9) . . ?
C13 C14 H14 114.1 . . ?
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
Rh1 O1 2.0369(17) 8_565 ?
Rh1 O1 2.0369(17) . ?
Rh1 C10 2.151(16) . ?
Rh1 C17 2.07(2) . ?
Rh1 C13 2.068(17) . ?
Rh1 C14 2.15(2) . ?
S1 C2 1.760(3) . ?
S1 C1 1.796(3) . ?
O1 C8 1.283(3) . ?
C8 C5 1.482(4) . ?
C8 C9 1.401(3) . ?
C5 C4 1.394(4) . ?
C5 C6 1.400(3) . ?
C4 H4 0.9500 . ?
C4 C3 1.380(4) . ?
C3 H3 0.9500 . ?
C3 C2 1.397(4) . ?
C10 H10 1.0000 . ?
C10 C17 1.393(7) . ?
C10 C11 1.508(7) . ?
C6 H6 0.9500 . ?
C6 C7 1.379(4) . ?
C17 H17 1.0000 . ?
C17 C16 1.514(7) . ?
C9 H9 0.9500 . ?
C2 C7 1.392(4) . ?
C7 H7 0.9500 . ?
C1 H1A 0.9800 . ?
C1 H1B 0.9800 . ?
C1 H1C 0.9800 . ?
C11 H11A 0.9900 . ?
C11 H11B 0.9900 . ?
C11 C12 1.531(6) . ?
C16 H16A 0.9900 . ?
C16 H16B 0.9900 . ?
C16 C15 1.532(7) . ?
C12 H12A 0.9900 . ?
C12 H12B 0.9900 . ?
C12 C13 1.513(7) . ?
C15 H15A 0.9900 . ?
C15 H15B 0.9900 . ?
C15 C14 1.521(7) . ?
C13 H13 1.0000 . ?
C13 C14 1.391(7) . ?
C14 H14 1.0000 . ?
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_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
Rh1 O1 C8 C5 -178.53(15) . . . . ?
Rh1 O1 C8 C9 1.2(4) . . . . ?
Rh1 C10 C17 C16 -110.1(18) . . . . ?
Rh1 C10 C11 C12 -15.1(11) . . . . ?
Rh1 C17 C16 C15 9.4(10) . . . . ?
Rh1 C13 C14 C15 96(2) . . . . ?
S1 C2 C7 C6 -178.6(2) . . . . ?
O1 C8 C5 C4 23.3(3) . . . . ?
O1 C8 C5 C6 -153.5(2) . . . . ?
O1 C8 C9 C8 -1.2(6) . . . 8_565 ?
C8 C5 C4 C3 -175.5(2) . . . . ?
C8 C5 C6 C7 174.4(2) . . . . ?
C5 C8 C9 C8 178.5(2) . . . 8_565 ?
C5 C4 C3 C2 0.6(4) . . . . ?
C5 C6 C7 C2 1.3(4) . . . . ?
C4 C5 C6 C7 -2.4(4) . . . . ?
C4 C3 C2 S1 177.6(2) . . . . ?
C4 C3 C2 C7 -1.7(4) . . . . ?
C3 C2 C7 C6 0.7(4) . . . . ?
C10 C17 C16 C15 95(2) . . . . ?
C10 C11 C12 C13 34.5(14) . . . . ?
C6 C5 C4 C3 1.4(4) . . . . ?
C17 C10 C11 C12 -90.0(17) . . . . ?
C17 C16 C15 C14 -27.7(13) . . . . ?
C9 C8 C5 C4 -156.5(3) . . . . ?
C9 C8 C5 C6 26.7(4) . . . . ?
C1 S1 C2 C3 -7.3(3) . . . . ?
C1 S1 C2 C7 172.0(2) . . . . ?
C11 C10 C17 Rh1 105.0(12) . . . . ?
C11 C10 C17 C16 -5(3) . . . . ?
C11 C12 C13 Rh1 -37.7(10) . . . . ?
C11 C12 C13 C14 49(3) . . . . ?
C16 C15 C14 Rh1 31.8(10) . . . . ?
C16 C15 C14 C13 -43(3) . . . . ?
C12 C13 C14 Rh1 -102(2) . . . . ?
C12 C13 C14 C15 -7(4) . . . . ?
