#------------------------------------------------------------------------------
#$Date: 2021-07-03 22:35:09 +0300 (Sat, 03 Jul 2021) $
#$Revision: 266941 $
#$URL: file:///home/coder/svn-repositories/cod/cif/4/51/88/4518858.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_4518858
loop_
_publ_author_name
'Barlow, Jeffrey M.'
'Ziller, Joseph W.'
'Yang, Jenny Y.'
_publ_section_title
;
 Inhibiting the Hydrogen Evolution Reaction (HER) with Proximal Cations: A
 Strategy for Promoting Selective Electrocatalytic Reduction
;
_journal_issue                   13
_journal_name_full               'ACS Catalysis'
_journal_page_first              8155
_journal_page_last               8164
_journal_paper_doi               10.1021/acscatal.1c01527
_journal_volume                  11
_journal_year                    2021
_chemical_formula_sum            'C9 H19 B F4 N O Rh S2'
_chemical_formula_weight         411.09
_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     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-2014/7
_cell_angle_alpha                116.5646(11)
_cell_angle_beta                 96.3920(12)
_cell_angle_gamma                103.0219(11)
_cell_formula_units_Z            2
_cell_length_a                   8.2674(9)
_cell_length_b                   9.8268(10)
_cell_length_c                   10.9563(11)
_cell_measurement_reflns_used    9799
_cell_measurement_temperature    88(2)
_cell_measurement_theta_max      29.09
_cell_measurement_theta_min      2.61
_cell_volume                     752.35(14)
_computing_cell_refinement       'Bruker SAINT 8.34a, 2013'
_computing_data_collection       'Bruker APEX2 2014.11-0, 2014'
_computing_data_reduction        'Bruker SAINT 8.34a, 2013'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_structure_solution    'Bruker SHELXTL 2014/4'
_diffrn_ambient_temperature      88(2)
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.902
_diffrn_measurement_device_type  'Bruker SMART APEX II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_unetI/netI     0.0182
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.902
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       0
_diffrn_reflns_number            3604
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.902
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         29.093
_diffrn_reflns_theta_min         2.143
_diffrn_source                   'fine-focus sealed tube'
_exptl_absorpt_coefficient_mu    1.445
_exptl_absorpt_correction_T_max  0.7458
_exptl_absorpt_correction_T_min  0.6406
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'TWINABS 2012/1'
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.815
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    not_measured
_exptl_crystal_description       Plate
_exptl_crystal_F_000             412
_exptl_crystal_size_max          0.372
_exptl_crystal_size_mid          0.215
_exptl_crystal_size_min          0.150
_refine_diff_density_max         1.626
_refine_diff_density_min         -0.517
_refine_diff_density_rms         0.085
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.068
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     175
_refine_ls_number_reflns         3604
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.068
_refine_ls_R_factor_all          0.0211
_refine_ls_R_factor_gt           0.0204
_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)+(0.0273P)²+0.7557P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0541
_refine_ls_wR_factor_ref         0.0546
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3513
_reflns_number_total             3604
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            cs1c01527_si_002.cif
_cod_data_source_block           jyy168
_cod_depositor_comments
;
The following automatic conversions were performed:

data item '_exptl_crystal_density_meas' value 'not_measured' was
changed to '?' -- the value is perceived as not measured.

Automatic conversion script
Id: cif_fix_values 7556 2019-12-06 15:28:31Z antanas 
;
_cod_original_cell_volume        752.34(14)
_cod_database_code               4518858
_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_min   0.616
_shelx_estimated_absorpt_t_max   0.812
_exptl_absorpt_special_details
; 
HKLF 5 dataset constructed from all observations involving domain 1 
5186 Corrected reflections written to file twin5.hkl 
Reflections merged according to point-group -1 
Single reflections that also occur in composites omitted 
Minimum and maximum apparent transmission:  0.6406  0.7458 
Additional spherical absorption correction applied with mu*r =  0.2000 
;
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
Rh1 Rh 0.56611(2) 0.77905(2) 0.50168(2) 0.00969(5) Uani 1 1 d . . . . .
S1 S 0.65387(7) 1.04615(6) 0.66931(5) 0.01290(10) Uani 1 1 d . . . . .
S2 S 0.42735(7) 0.51307(6) 0.33665(5) 0.01178(10) Uani 1 1 d . . . . .
O1 O 0.8889(2) 0.8094(2) 0.4055(2) 0.0261(4) Uani 1 1 d . . . . .
N1 N 0.3478(2) 0.7643(2) 0.58334(19) 0.0118(3) Uani 1 1 d . . . . .
H1 H 0.3656 0.7193 0.6477 0.014 Uiso 1 1 calc R U . . .
C1 C 0.7627(3) 0.7936(3) 0.4390(2) 0.0151(4) Uani 1 1 d . . . . .
C2 C 0.3257(3) 0.9235(3) 0.6699(2) 0.0157(4) Uani 1 1 d . . . . .
H2A H 0.2386 0.9130 0.7230 0.019 Uiso 1 1 calc R U . . .
H2B H 0.2852 0.9636 0.6078 0.019 Uiso 1 1 calc R U . . .
C3 C 0.4943(3) 1.0405(3) 0.7714(2) 0.0179(4) Uani 1 1 d . . . . .
H3A H 0.5303 1.0060 0.8393 0.021 Uiso 1 1 calc R U . . .
H3B H 0.4821 1.1483 0.8245 0.021 Uiso 1 1 calc R U . . .
C4 C 0.8524(3) 1.0991(3) 0.7941(2) 0.0170(4) Uani 1 1 d . . . . .
H4A H 0.9496 1.1276 0.7557 0.020 Uiso 1 1 calc R U . . .
H4B H 0.8600 1.1955 0.8827 0.020 Uiso 1 1 calc R U . . .
C5 C 0.8715(4) 0.9692(3) 0.8280(3) 0.0273(6) Uani 1 1 d . . . . .
H5A H 0.8573 0.8709 0.7405 0.041 Uiso 1 1 calc R U . . .
H5B H 0.7841 0.9488 0.8765 0.041 Uiso 1 1 calc R U . . .
H5C H 0.9855 1.0037 0.8888 0.041 Uiso 1 1 calc R U . . .
C6 C 0.1927(3) 0.6487(3) 0.4693(2) 0.0137(4) Uani 1 1 d . . . . .
H6A H 0.1667 0.6898 0.4042 0.016 Uiso 1 1 calc R U . . .
H6B H 0.0932 0.6348 0.5100 0.016 Uiso 1 1 calc R U . . .
C7 C 0.2253(3) 0.4900(3) 0.3902(2) 0.0136(4) Uani 1 1 d . . . . .
H7A H 0.1300 0.4179 0.3056 0.016 Uiso 1 1 calc R U . . .
H7B H 0.2281 0.4397 0.4508 0.016 Uiso 1 1 calc R U . . .
C8 C 0.3664(3) 0.5121(3) 0.1705(2) 0.0168(4) Uani 1 1 d . . . . .
H8A H 0.2976 0.5858 0.1830 0.020 Uiso 1 1 calc R U . . .
H8B H 0.4711 0.5523 0.1451 0.020 Uiso 1 1 calc R U . . .
C9 C 0.2636(3) 0.3462(3) 0.0508(2) 0.0190(5) Uani 1 1 d . . . . .
H9A H 0.2322 0.3522 -0.0352 0.029 Uiso 1 1 calc R U . . .
H9B H 0.1595 0.3059 0.0751 0.029 Uiso 1 1 calc R U . . .
H9C H 0.3327 0.2737 0.0353 0.029 Uiso 1 1 calc R U . . .
B1 B 0.2478(4) 0.6709(4) -0.1533(3) 0.0219(5) Uani 1 1 d . . . . .
F1 F 0.1302(2) 0.7539(2) -0.12889(17) 0.0330(4) Uani 1 1 d . . . . .
F2 F 0.4069(2) 0.7815(2) -0.13119(18) 0.0308(4) Uani 1 1 d . . . . .
F3 F 0.2693(3) 0.6118(2) -0.06287(19) 0.0412(4) Uani 1 1 d . . . . .
F4 F 0.2028(2) 0.55037(17) -0.29413(15) 0.0238(3) Uani 1 1 d . . . . .
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'
B B 0.0013 0.0007 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 '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'
F F 0.0171 0.0103 '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'
Rh Rh -1.1178 0.9187 '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
C1 Rh1 N1 177.09(9) . . ?
C1 Rh1 S1 93.79(7) . . ?
N1 Rh1 S1 85.16(5) . . ?
C1 Rh1 S2 96.07(7) . . ?
N1 Rh1 S2 85.18(5) . . ?
S1 Rh1 S2 169.39(2) . . ?
C4 S1 C3 102.51(11) . . ?
C4 S1 Rh1 111.43(8) . . ?
C3 S1 Rh1 98.90(8) . . ?
C8 S2 C7 102.78(10) . . ?
C8 S2 Rh1 105.39(8) . . ?
C7 S2 Rh1 98.77(7) . . ?
C6 N1 C2 112.75(17) . . ?
C6 N1 Rh1 110.68(13) . . ?
C2 N1 Rh1 113.02(13) . . ?
O1 C1 Rh1 176.8(2) . . ?
N1 C2 C3 109.84(18) . . ?
C2 C3 S1 108.07(15) . . ?
C5 C4 S1 114.82(17) . . ?
N1 C6 C7 108.91(17) . . ?
C6 C7 S2 111.95(15) . . ?
C9 C8 S2 112.52(16) . . ?
F3 B1 F1 112.8(2) . . ?
F3 B1 F4 111.8(2) . . ?
F1 B1 F4 110.0(2) . . ?
F3 B1 F2 107.9(2) . . ?
F1 B1 F2 106.7(2) . . ?
F4 B1 F2 107.3(2) . . ?
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 C1 1.834(2) . ?
Rh1 N1 2.1065(18) . ?
Rh1 S1 2.3070(6) . ?
Rh1 S2 2.3189(6) . ?
S1 C4 1.820(2) . ?
S1 C3 1.829(2) . ?
S2 C8 1.830(2) . ?
S2 C7 1.831(2) . ?
O1 C1 1.145(3) . ?
N1 C6 1.488(3) . ?
N1 C2 1.490(3) . ?
C2 C3 1.513(3) . ?
C4 C5 1.515(3) . ?
C6 C7 1.513(3) . ?
C8 C9 1.522(3) . ?
B1 F3 1.368(3) . ?
B1 F1 1.379(3) . ?
B1 F4 1.401(3) . ?
B1 F2 1.421(3) . ?
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
C6 N1 C2 C3 -172.90(17) . . . . ?
Rh1 N1 C2 C3 -46.4(2) . . . . ?
N1 C2 C3 S1 55.8(2) . . . . ?
C4 S1 C3 C2 -151.88(16) . . . . ?
Rh1 S1 C3 C2 -37.45(16) . . . . ?
C3 S1 C4 C5 70.1(2) . . . . ?
Rh1 S1 C4 C5 -34.8(2) . . . . ?
C2 N1 C6 C7 -178.34(17) . . . . ?
Rh1 N1 C6 C7 53.96(19) . . . . ?
N1 C6 C7 S2 -50.3(2) . . . . ?
C8 S2 C7 C6 -85.04(17) . . . . ?
Rh1 S2 C7 C6 23.04(16) . . . . ?
C7 S2 C8 C9 -73.67(18) . . . . ?
Rh1 S2 C8 C9 -176.65(15) . . . . ?
