# Electronic Supplementary Material (ESI) for Chemical Science.
# This journal is © The Royal Society of Chemistry 2018

####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_yoshi68m
_database_code_depnum_ccdc_archive 'CCDC 1826866'
_audit_update_record             
;
2018-03-01 deposited with the CCDC.
2018-07-25 downloaded from the CCDC.
;
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C24 H19 Cl4 Rh'
_chemical_formula_iupac          ?
_chemical_formula_weight         552.10

_chemical_melting_point          ?

_space_group_crystal_system      monoclinic
_space_group_name_H-M_alt        'P 1 21/c 1'
_space_group_name_Hall           '-P 2ybc'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'

_cell_length_a                   14.3151(3)
_cell_length_b                   6.87740(10)
_cell_length_c                   23.4347(5)
_cell_angle_alpha                90
_cell_angle_beta                 106.9586(7)
_cell_angle_gamma                90
_cell_volume                     2206.84(7)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    9897
_cell_measurement_theta_min      2.6632
_cell_measurement_theta_max      33.0208
_cell_measurement_temperature    190.(2)

_exptl_crystal_description       block
_exptl_crystal_colour            red
_exptl_crystal_size_max          0.260
_exptl_crystal_size_mid          0.140
_exptl_crystal_size_min          0.120
_exptl_crystal_density_diffrn    1.662
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1104

_exptl_absorpt_coefficient_mu    1.267
_exptl_absorpt_correction_type   Multi-Scan
_exptl_absorpt_process_details   
;
SADABS-2016/2 - Bruker AXS area detector scaling and absorption correction
;
_exptl_absorpt_correction_T_min  0.77
_exptl_absorpt_correction_T_max  0.86

_exptl_special_details           
;
;

_diffrn_ambient_temperature      190.(2)

_diffrn_source                   'Incoatec microfocus source'
_diffrn_source_type              'Bruker D8 Quest'

_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_monochromator  'Multilayer Mirror'

_diffrn_measurement_device_type  'Photon II CPADs detector'
_diffrn_measurement_method       'phi and omega scans'

_diffrn_detector_area_resol_mean 7.4074

_diffrn_reflns_number            47003
_diffrn_reflns_av_R_equivalents  0.0438
_diffrn_reflns_av_unetI/netI     0.0329
_diffrn_reflns_theta_min         2.66
_diffrn_reflns_theta_max         33.28
_diffrn_reflns_theta_full        33.28
_diffrn_measured_fraction_theta_max 0.994
_diffrn_measured_fraction_theta_full 0.994
_diffrn_reflns_limit_h_min       -22
_diffrn_reflns_limit_h_max       22
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_l_min       -36
_diffrn_reflns_limit_l_max       36

_refine_special_details          
;
;

_reflns_number_total             8473
_reflns_number_gt                7222
_reflns_threshold_expression     'I > 2σ(I)'

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_R_factor_all          0.0387
_refine_ls_R_factor_gt           0.0292
_refine_ls_wR_factor_gt          0.0611
_refine_ls_wR_factor_ref         0.0660
_refine_ls_goodness_of_fit_ref   1.043
_refine_ls_restrained_S_all      1.043
_refine_ls_number_reflns         8473
_refine_ls_number_parameters     262
_refine_ls_number_restraints     0
_refine_ls_number_constraints    ?
_refine_ls_hydrogen_treatment    constr
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0235P)²+1.2109P] where P=(Fo²+2Fc²)/3'

_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   ?

_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_diff_density_max         0.772
_refine_diff_density_min         -0.644
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?

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'
Cl Cl 0.1484 0.1585 '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'

_computing_data_collection       'APEX3 (Bruker AXS Inc., 2017)'
_computing_cell_refinement       'SAINT V8.38A (Bruker AXS Inc., 2017)'
_computing_data_reduction        'SAINT V8.38A (Bruker AXS Inc., 2017)'
_computing_structure_solution    'XS, VERSION 2013/1'
_computing_structure_refinement  'SHELXL-2016/6 (Sheldrick, 2016)'
_computing_molecular_graphics    ?
_computing_publication_material  'APEX3 (Bruker AXS Inc., 2017)'

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
Rh Rh1 0.11238(2) 0.59705(2) 0.05019(2) 0.01620(3) Uani d . . . 1 . .
C C1 0.11031(11) 0.7063(2) 0.13710(7) 0.0195(3) Uani d . . . 1 . .
C C2 0.20769(11) 0.6422(2) 0.13798(7) 0.0190(3) Uani d . . . 1 . .
C C3 0.23977(12) 0.7667(2) 0.09705(7) 0.0208(3) Uani d . . . 1 . .
C C4 0.15971(13) 0.8908(2) 0.06843(7) 0.0220(3) Uani d . . . 1 . .
H H4 0.160024 0.991669 0.037749 0.026 Uiso calc U . R 1 . .
C C5 0.08096(12) 0.8536(2) 0.09257(7) 0.0214(3) Uani d . . . 1 . .
H H5 0.01708 0.924024 0.081697 0.026 Uiso calc U . R 1 . .
C C6 0.05166(12) 0.6456(2) 0.17586(7) 0.0203(3) Uani d . . . 1 . .
C C7 0.09667(14) 0.6134(2) 0.23636(8) 0.0257(3) Uani d . . . 1 . .
H H7 0.165866 0.607129 0.250973 0.031 Uiso calc U . R 1 . .
C C8 0.04093(16) 0.5906(3) 0.27524(8) 0.0315(4) Uani d . . . 1 . .
H H8 0.07199 0.57053 0.316542 0.038 Uiso calc U . R 1 . .
C C9 -0.05991(16) 0.5969(3) 0.25410(9) 0.0324(4) Uani d . . . 1 . .
H H9 -0.097932 0.58197 0.280951 0.039 Uiso calc U . R 1 . .
C C10 -0.10558(15) 0.6249(3) 0.19384(9) 0.0311(4) Uani d . . . 1 . .
H H10 -0.174863 0.62752 0.179464 0.037 Uiso calc U . R 1 . .
C C11 -0.05062(13) 0.6491(2) 0.15441(8) 0.0255(3) Uani d . . . 1 . .
H H11 -0.082091 0.66789 0.1131 0.031 Uiso calc U . R 1 . .
C C12 0.26817(12) 0.4950(2) 0.17858(7) 0.0212(3) Uani d . . . 1 . .
C C13 0.35286(14) 0.5526(3) 0.22167(8) 0.0319(4) Uani d . . . 1 . .
H H13 0.373013 0.684645 0.22382 0.038 Uiso calc U . R 1 . .
C C14 0.40820(15) 0.4176(3) 0.26165(9) 0.0411(5) Uani d . . . 1 . .
H H14 0.465546 0.457934 0.291382 0.049 Uiso calc U . R 1 . .
C C15 0.37978(16) 0.2249(3) 0.25813(9) 0.0404(5) Uani d . . . 1 . .
H H15 0.417521 0.132817 0.285507 0.049 Uiso calc U . R 1 . .
C C16 0.29675(16) 0.1662(3) 0.21494(9) 0.0364(4) Uani d . . . 1 . .
H H16 0.277757 0.033381 0.212394 0.044 Uiso calc U . R 1 . .
C C17 0.24059(13) 0.3006(3) 0.17503(8) 0.0274(3) Uani d . . . 1 . .
H H17 0.183365 0.259471 0.145349 0.033 Uiso calc U . R 1 . .
C C18 0.33681(12) 0.7740(3) 0.08717(7) 0.0251(3) Uani d . . . 1 . .
C C19 0.39394(14) 0.6095(3) 0.08858(9) 0.0332(4) Uani d . . . 1 . .
H H19 0.370934 0.485384 0.096167 0.04 Uiso calc U . R 1 . .
C C20 0.48463(16) 0.6272(4) 0.07886(11) 0.0458(6) Uani d . . . 1 . .
H H20 0.523002 0.51445 0.078892 0.055 Uiso calc U . R 1 . .
C C21 0.51939(16) 0.8073(5) 0.06917(11) 0.0529(7) Uani d . . . 1 . .
H H21 0.581983 0.818444 0.063142 0.064 Uiso calc U . R 1 . .
C C22 0.46373(16) 0.9709(4) 0.06821(10) 0.0477(6) Uani d . . . 1 . .
H H22 0.488043 1.094849 0.061616 0.057 Uiso calc U . R 1 . .
C C23 0.37271(15) 0.9556(3) 0.07678(9) 0.0342(4) Uani d . . . 1 . .
H H23 0.33422 1.068852 0.075621 0.041 Uiso calc U . R 1 . .
C C24 0.2487(2) 0.7349(3) 0.91487(13) 0.0569(7) Uani d . . . 1 . .
H H24A 0.187349 0.659439 0.900927 0.068 Uiso calc U . R 1 . .
H H24B 0.289278 0.674596 0.952246 0.068 Uiso calc U . R 1 . .
Cl Cl1 0.19762(3) 0.36789(6) 0.00824(2) 0.02537(8) Uani d . . . 1 . .
Cl Cl2 -0.00485(3) 0.33898(5) 0.05005(2) 0.02057(7) Uani d . . . 1 . .
Cl Cl3 0.31159(4) 0.72338(10) 0.86052(3) 0.05022(14) Uani d . . . 1 . .
Cl Cl4 0.22117(4) 0.97374(8) 0.92945(2) 0.04217(12) Uani d . . . 1 . .


_geom_special_details            
;

All esds (except the esd in the dihedral angle between two l.s. planes)
are estimated using the full covariance matrix.  The cell esds are taken
into account individually in the estimation of esds in distances, angles
and torsion angles; correlations between esds in cell parameters are only
used when they are defined by crystal symmetry.  An approximate (isotropic)
treatment of cell esds is used for estimating esds involving l.s. planes.
;

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
Rh1 C2 . 2.1338(15) ?
Rh1 C4 . 2.1341(15) ?
Rh1 C5 . 2.1358(16) ?
Rh1 C3 . 2.1736(15) ?
Rh1 C1 . 2.1791(15) ?
Rh1 Cl1 . 2.3747(4) ?
Rh1 Cl2 . 2.4418(4) ?
Rh1 Cl2 3_565 2.4437(4) ?
C1 C5 . 1.427(2) ?
C1 C2 . 1.456(2) ?
C1 C6 . 1.466(2) ?
C2 C3 . 1.456(2) ?
C2 C12 . 1.483(2) ?
C3 C4 . 1.429(2) ?
C3 C18 . 1.474(2) ?
C4 C5 . 1.424(2) ?
C6 C7 . 1.393(2) ?
C6 C11 . 1.403(2) ?
C7 C8 . 1.384(3) ?
C8 C9 . 1.383(3) ?
C9 C10 . 1.386(3) ?
C10 C11 . 1.387(3) ?
C12 C17 . 1.389(2) ?
C12 C13 . 1.390(2) ?
C13 C14 . 1.391(3) ?
C14 C15 . 1.382(3) ?
C15 C16 . 1.378(3) ?
C16 C17 . 1.392(2) ?
C18 C19 . 1.391(3) ?
C18 C23 . 1.399(2) ?
C19 C20 . 1.387(3) ?
C20 C21 . 1.378(4) ?
C21 C22 . 1.375(4) ?
C22 C23 . 1.379(3) ?
C24 Cl4 . 1.746(2) ?
C24 Cl3 . 1.763(3) ?

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
C2 Rh1 C4 . . 65.96(6) ?
C2 Rh1 C5 . . 66.02(6) ?
C4 Rh1 C5 . . 38.97(6) ?
C2 Rh1 C3 . . 39.51(6) ?
C4 Rh1 C3 . . 38.75(6) ?
C5 Rh1 C3 . . 65.24(6) ?
C2 Rh1 C1 . . 39.45(6) ?
C4 Rh1 C1 . . 64.94(6) ?
C5 Rh1 C1 . . 38.60(6) ?
C3 Rh1 C1 . . 65.22(6) ?
C2 Rh1 Cl1 . . 103.56(4) ?
C4 Rh1 Cl1 . . 122.67(5) ?
C5 Rh1 Cl1 . . 160.74(5) ?
C3 Rh1 Cl1 . . 96.24(5) ?
C1 Rh1 Cl1 . . 139.86(4) ?
C2 Rh1 Cl2 . . 110.68(4) ?
C4 Rh1 Cl2 . . 150.03(5) ?
C5 Rh1 Cl2 . . 111.30(5) ?
C3 Rh1 Cl2 . . 149.98(4) ?
C1 Rh1 Cl2 . . 93.17(4) ?
Cl1 Rh1 Cl2 . . 87.300(15) ?
C2 Rh1 Cl2 . 3_565 161.25(4) ?
C4 Rh1 Cl2 . 3_565 95.53(4) ?
C5 Rh1 Cl2 . 3_565 98.01(4) ?
C3 Rh1 Cl2 . 3_565 126.11(4) ?
C1 Rh1 Cl2 . 3_565 131.29(4) ?
Cl1 Rh1 Cl2 . 3_565 88.693(14) ?
Cl2 Rh1 Cl2 . 3_565 83.660(13) ?
C5 C1 C2 . . 107.56(14) ?
C5 C1 C6 . . 123.76(14) ?
C2 C1 C6 . . 128.59(14) ?
C5 C1 Rh1 . . 69.06(9) ?
C2 C1 Rh1 . . 68.60(8) ?
C6 C1 Rh1 . . 130.33(11) ?
C3 C2 C1 . . 107.29(13) ?
C3 C2 C12 . . 125.93(14) ?
C1 C2 C12 . . 126.36(14) ?
C3 C2 Rh1 . . 71.72(9) ?
C1 C2 Rh1 . . 71.95(8) ?
C12 C2 Rh1 . . 127.48(11) ?
C4 C3 C2 . . 107.23(14) ?
C4 C3 C18 . . 124.71(14) ?
C2 C3 C18 . . 128.02(14) ?
C4 C3 Rh1 . . 69.13(9) ?
C2 C3 Rh1 . . 68.77(8) ?
C18 C3 Rh1 . . 128.98(12) ?
C5 C4 C3 . . 109.00(14) ?
C5 C4 Rh1 . . 70.58(9) ?
C3 C4 Rh1 . . 72.12(9) ?
C4 C5 C1 . . 108.65(14) ?
C4 C5 Rh1 . . 70.45(9) ?
C1 C5 Rh1 . . 72.34(9) ?
C7 C6 C11 . . 119.46(16) ?
C7 C6 C1 . . 119.83(15) ?
C11 C6 C1 . . 119.98(15) ?
C8 C7 C6 . . 120.24(17) ?
C9 C8 C7 . . 120.16(18) ?
C8 C9 C10 . . 120.15(17) ?
C9 C10 C11 . . 120.32(18) ?
C10 C11 C6 . . 119.66(17) ?
C17 C12 C13 . . 119.34(16) ?
C17 C12 C2 . . 121.07(14) ?
C13 C12 C2 . . 119.59(15) ?
C12 C13 C14 . . 120.28(19) ?
C15 C14 C13 . . 119.99(19) ?
C16 C15 C14 . . 120.06(18) ?
C15 C16 C17 . . 120.30(19) ?
C12 C17 C16 . . 120.03(17) ?
C19 C18 C23 . . 119.15(17) ?
C19 C18 C3 . . 122.91(16) ?
C23 C18 C3 . . 117.94(17) ?
C20 C19 C18 . . 119.8(2) ?
C21 C20 C19 . . 120.4(2) ?
C22 C21 C20 . . 120.2(2) ?
C21 C22 C23 . . 120.2(2) ?
C22 C23 C18 . . 120.3(2) ?
Cl4 C24 Cl3 . . 112.07(13) ?
Rh1 Cl2 Rh1 . 3_565 96.340(13) ?


_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: dichloromethane'
