# Electronic Supplementary Material (ESI) for Chemical Communications.
# This journal is © The Royal Society of Chemistry 2016

####################################################################### 
# 
# 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_x1511015
_database_code_depnum_ccdc_archive 'CCDC 1447440'
_audit_update_record             
;
2016-01-14 deposited with the CCDC.
2016-02-29 downloaded from the CCDC.
;
_audit_creation_date             2016-01-14
_audit_creation_method           
;
Olex2 1.2
(compiled 2015.09.30 svn.r3233 for OlexSys, GUI svn.r5103)
;
_chemical_name_common            ?
_chemical_name_systematic        (Cp*H)Rh(bpy)Cl
_chemical_formula_moiety         'C20 H24 Cl N2 Rh, 0.5(C2 H4 Cl4)'
_chemical_formula_sum            'C21 H26 Cl3 N2 Rh'
_chemical_formula_weight         515.70
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 '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 0.3639 0.7018 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Rh Rh 0.0927 3.6045 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_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.
;
_space_group_crystal_system      orthorhombic
_space_group_IT_number           62
_space_group_name_H-M_alt        'P n m a'
_space_group_name_Hall           '-P 2ac 2n'
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'

_cell_length_a                   22.5211(11)
_cell_length_b                   12.1599(6)
_cell_length_c                   7.8427(4)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     2147.76(19)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    9994
_cell_measurement_temperature    100
_cell_measurement_theta_max      72.35
_cell_measurement_theta_min      3.93
_shelx_estimated_absorpt_T_max   0.723
_shelx_estimated_absorpt_T_min   0.166
_exptl_absorpt_coefficient_mu    9.921
_exptl_absorpt_correction_T_max  0.7647
_exptl_absorpt_correction_T_min  0.1358
_exptl_absorpt_correction_type   numerical
_exptl_absorpt_process_details   
;
SADABS-2014/5 (Bruker,2014/5) was used for absorption correction.
wR2(int) was 0.0670 before and 0.0397 after correction.
The Ratio of minimum to maximum transmission is 0.1776.
The λ/2 correction factor is 0.00150.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear light brown'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    brown
_exptl_crystal_density_diffrn    1.595
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       plate
_exptl_crystal_F_000             1048
_exptl_crystal_size_max          0.282
_exptl_crystal_size_mid          0.143
_exptl_crystal_size_min          0.035
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0258
_diffrn_reflns_av_unetI/netI     0.0153
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_limit_h_max       27
_diffrn_reflns_limit_h_min       -27
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       9
_diffrn_reflns_limit_l_min       -9
_diffrn_reflns_number            18815
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 1.000
_diffrn_reflns_theta_full        67.679
_diffrn_reflns_theta_max         72.338
_diffrn_reflns_theta_min         3.926
_diffrn_ambient_temperature      100
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_source                   ?
_diffrn_special_details          ?
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2191
_reflns_number_total             2224
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       ?
_computing_data_collection       ?
_computing_data_reduction        ?
_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    'olex2.solve (Bourhis et al., 2015)'
_refine_diff_density_max         0.369
_refine_diff_density_min         -0.694
_refine_diff_density_rms         0.093
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.113
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     136
_refine_ls_number_reflns         2224
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0224
_refine_ls_R_factor_gt           0.0220
_refine_ls_restrained_S_all      1.113
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0278P)²+2.0759P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0549
_refine_ls_wR_factor_ref         0.0551
_refine_special_details          ?
_olex2_refinement_description    
;
1. Others
 Fixed Sof: H4A(0.5) H4B(0.5) H4C(0.5) H12A(0.5) H12B(0.5)
 Fixed U12: Rh1(0) Cl1(0) C1(0) C4(0) Cl2(0) Cl3(0) C12(0)
 Fixed U23: Rh1(0) Cl1(0) C1(0) C4(0) Cl2(0) Cl3(0) C12(0)
 Fixed Uiso: H1(0.021) H4A(0.034) H4B(0.034) H4C(0.034) H5A(0.034) H5B(0.034)
 H5C(0.034) H6A(0.032) H6B(0.032) H6C(0.032) H7(0.02) H8(0.022) H9(0.024)
 H10(0.021) H12A(0.059) H12B(0.059)
 Fixed X: H1(0.6227) H4A(0.5421) H4B(0.5468) H4C(0.4968) H5A(0.6272)
 H5B(0.5625) H5C(0.5719) H6A(0.4867) H6B(0.5182) H6C(0.4584) H7(0.6305)
 H8(0.6796) H9(0.7286) H10(0.7258) H12A(0.3057) H12B(0.3057)
 Fixed Y: Rh1(0.25) Cl1(0.25) C1(0.25) H1(0.25) C4(0.25) H4A(0.3188)
 H4B(0.1876) H4C(0.2436) H5A(0.47) H5B(0.4779) H5C(0.5095) H6A(0.3443)
 H6B(0.4495) H6C(0.4021) H7(0.5023) H8(0.6131) H9(0.5304) H10(0.3388) Cl2(0.25)
 Cl3(0.25) C12(0.25) H12A(0.1842) H12B(0.3158)
 Fixed Z: H1(0.5528) H4A(0.7274) H4B(0.7382) H4C(0.622) H5A(0.4547)
 H5B(0.5383) H5C(0.342) H6A(0.0334) H6B(0.1158) H6C(0.1976) H7(0.1075) H8(-
 0.087) H9(-0.3194) H10(-0.3485) H12A(0.5284) H12B(0.5284)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
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 0.61650(2) 0.2500 0.19100(2) 0.01147(8) Uani 1 2 d S T P . .
Cl1 Cl 0.72198(3) 0.2500 0.30711(7) 0.01674(14) Uani 1 2 d S T P . .
N1 N 0.64992(6) 0.35836(12) 0.00302(18) 0.0135(3) Uani 1 1 d . . . . .
C1 C 0.58088(11) 0.2500 0.5103(3) 0.0173(5) Uani 1 2 d S T P . .
H1 H 0.6227 0.2500 0.5528 0.021 Uiso 1 2 calc RS T P . .
C2 C 0.57255(8) 0.34315(15) 0.3839(2) 0.0153(4) Uani 1 1 d . . . . .
C3 C 0.53143(7) 0.30879(16) 0.2537(2) 0.0151(4) Uani 1 1 d . . . . .
C4 C 0.53771(13) 0.2500 0.6635(3) 0.0225(6) Uani 1 2 d S T P . .
H4A H 0.5421 0.3188 0.7274 0.034 Uiso 0.5 1 calc GR . . A -1
H4B H 0.5468 0.1876 0.7382 0.034 Uiso 0.5 1 calc GR . . A -1
H4C H 0.4968 0.2436 0.6220 0.034 Uiso 0.5 1 calc GR . . A -1
C5 C 0.58459(9) 0.46035(17) 0.4341(3) 0.0230(4) Uani 1 1 d . . . . .
H5A H 0.6272 0.4700 0.4547 0.034 Uiso 1 1 calc GR . . . .
H5B H 0.5625 0.4779 0.5383 0.034 Uiso 1 1 calc GR . . . .
H5C H 0.5719 0.5095 0.3420 0.034 Uiso 1 1 calc GR . . . .
C6 C 0.49558(9) 0.38256(17) 0.1403(3) 0.0215(4) Uani 1 1 d . . . . .
H6A H 0.4867 0.3443 0.0334 0.032 Uiso 1 1 calc GR . . . .
H6B H 0.5182 0.4495 0.1158 0.032 Uiso 1 1 calc GR . . . .
H6C H 0.4584 0.4021 0.1976 0.032 Uiso 1 1 calc GR . . . .
C7 C 0.65072(8) 0.46870(15) 0.0149(2) 0.0169(4) Uani 1 1 d . . . . .
H7 H 0.6305 0.5023 0.1075 0.020 Uiso 1 1 calc R . . . .
C8 C 0.67948(8) 0.53546(16) -0.1007(2) 0.0180(4) Uani 1 1 d . . . . .
H8 H 0.6796 0.6131 -0.0870 0.022 Uiso 1 1 calc R . . . .
C9 C 0.70833(8) 0.48657(17) -0.2378(3) 0.0202(4) Uani 1 1 d . . . . .
H9 H 0.7286 0.5304 -0.3194 0.024 Uiso 1 1 calc R . . . .
C10 C 0.70716(8) 0.37346(16) -0.2540(2) 0.0179(4) Uani 1 1 d . . . . .
H10 H 0.7258 0.3388 -0.3485 0.021 Uiso 1 1 calc R . . . .
C11 C 0.67847(7) 0.31087(15) -0.1307(2) 0.0145(4) Uani 1 1 d . . . . .
Cl2 Cl 0.35746(4) 0.2500 0.75742(10) 0.03189(17) Uani 1 2 d S T P . .
Cl3 Cl 0.38737(3) 0.2500 0.39573(10) 0.03065(17) Uani 1 2 d S T P . .
C12 C 0.33088(15) 0.2500 0.5460(5) 0.0494(11) Uani 1 2 d S T P . .
H12A H 0.3057 0.1842 0.5284 0.059 Uiso 0.5 1 calc R . . . .
H12B H 0.3057 0.3158 0.5284 0.059 Uiso 0.5 1 calc R . . . .


_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_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Rh1 Cl1 2.5440(6) . ?
Rh1 N1 2.1156(15) 8_565 ?
Rh1 N1 2.1157(15) . ?
Rh1 C2 2.1334(18) 8_565 ?
Rh1 C2 2.1334(18) . ?
Rh1 C3 2.1032(17) . ?
Rh1 C3 2.1031(17) 8_565 ?
N1 C7 1.345(2) . ?
N1 C11 1.359(2) . ?
C1 H1 1.0000 . ?
C1 C2 1.517(2) . ?
C1 C2 1.517(2) 8_565 ?
C1 C4 1.545(4) . ?
C2 C3 1.440(3) . ?
C2 C5 1.503(3) . ?
C3 C3 1.430(4) 8_565 ?
C3 C6 1.499(3) . ?
C4 H4A 0.9800 . ?
C4 H4B 0.9800 . ?
C4 H4C 0.9800 . ?
C5 H5A 0.9800 . ?
C5 H5B 0.9800 . ?
C5 H5C 0.9800 . ?
C6 H6A 0.9800 . ?
C6 H6B 0.9800 . ?
C6 H6C 0.9800 . ?
C7 H7 0.9500 . ?
C7 C8 1.378(3) . ?
C8 H8 0.9500 . ?
C8 C9 1.390(3) . ?
C9 H9 0.9500 . ?
C9 C10 1.382(3) . ?
C10 H10 0.9500 . ?
C10 C11 1.390(3) . ?
C11 C11 1.480(4) 8_565 ?
Cl2 C12 1.763(4) . ?
Cl3 C12 1.734(3) . ?
C12 H12A 0.9900 . ?
C12 H12B 0.9900 . ?

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
N1 Rh1 Cl1 85.26(4) . . ?
N1 Rh1 Cl1 85.26(4) 8_565 . ?
N1 Rh1 N1 77.04(8) 8_565 . ?
N1 Rh1 C2 171.82(6) 8_565 . ?
N1 Rh1 C2 109.18(6) . . ?
N1 Rh1 C2 109.18(7) 8_565 8_565 ?
N1 Rh1 C2 171.82(6) . 8_565 ?
C2 Rh1 Cl1 100.34(5) . . ?
C2 Rh1 Cl1 100.34(5) 8_565 . ?
C2 Rh1 C2 64.14(10) 8_565 . ?
C3 Rh1 Cl1 140.07(5) . . ?
C3 Rh1 Cl1 140.07(5) 8_565 . ?
C3 Rh1 N1 134.32(6) . 8_565 ?
C3 Rh1 N1 105.98(6) 8_565 8_565 ?
C3 Rh1 N1 105.98(6) . . ?
C3 Rh1 N1 134.32(6) 8_565 . ?
C3 Rh1 C2 65.92(7) . 8_565 ?
C3 Rh1 C2 39.74(7) . . ?
C3 Rh1 C2 39.73(7) 8_565 8_565 ?
C3 Rh1 C2 65.92(7) 8_565 . ?
C3 Rh1 C3 39.75(10) 8_565 . ?
C7 N1 Rh1 125.30(13) . . ?
C7 N1 C11 118.09(16) . . ?
C11 N1 Rh1 116.19(12) . . ?
C2 C1 H1 109.5 8_565 . ?
C2 C1 H1 109.5 . . ?
C2 C1 C2 96.6(2) 8_565 . ?
C2 C1 C4 115.48(15) 8_565 . ?
C2 C1 C4 115.48(15) . . ?
C4 C1 H1 109.5 . . ?
C1 C2 Rh1 90.56(12) . . ?
C3 C2 Rh1 69.00(10) . . ?
C3 C2 C1 109.05(16) . . ?
C3 C2 C5 125.22(17) . . ?
C5 C2 Rh1 127.25(13) . . ?
C5 C2 C1 120.95(16) . . ?
C2 C3 Rh1 71.26(10) . . ?
C2 C3 C6 126.39(17) . . ?
C3 C3 Rh1 70.12(5) 8_565 . ?
C3 C3 C2 106.86(11) 8_565 . ?
C3 C3 C6 126.75(11) 8_565 . ?
C6 C3 Rh1 123.73(13) . . ?
C1 C4 H4A 109.5 . . ?
C1 C4 H4B 109.5 . . ?
C1 C4 H4C 109.5 . . ?
H4A C4 H4B 109.5 . . ?
H4A C4 H4C 109.5 . . ?
H4B C4 H4C 109.5 . . ?
C2 C5 H5A 109.5 . . ?
C2 C5 H5B 109.5 . . ?
C2 C5 H5C 109.5 . . ?
H5A C5 H5B 109.5 . . ?
H5A C5 H5C 109.5 . . ?
H5B C5 H5C 109.5 . . ?
C3 C6 H6A 109.5 . . ?
C3 C6 H6B 109.5 . . ?
C3 C6 H6C 109.5 . . ?
H6A C6 H6B 109.5 . . ?
H6A C6 H6C 109.5 . . ?
H6B C6 H6C 109.5 . . ?
N1 C7 H7 118.4 . . ?
N1 C7 C8 123.25(18) . . ?
C8 C7 H7 118.4 . . ?
C7 C8 H8 120.8 . . ?
C7 C8 C9 118.46(18) . . ?
C9 C8 H8 120.8 . . ?
C8 C9 H9 120.4 . . ?
C10 C9 C8 119.21(18) . . ?
C10 C9 H9 120.4 . . ?
C9 C10 H10 120.3 . . ?
C9 C10 C11 119.34(18) . . ?
C11 C10 H10 120.3 . . ?
N1 C11 C10 121.62(17) . . ?
N1 C11 C11 115.15(10) . 8_565 ?
C10 C11 C11 123.20(11) . 8_565 ?
Cl2 C12 H12A 109.0 . . ?
Cl2 C12 H12B 109.0 . . ?
Cl3 C12 Cl2 113.0(2) . . ?
Cl3 C12 H12A 109.0 . . ?
Cl3 C12 H12B 109.0 . . ?
H12A C12 H12B 107.8 . . ?

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 N1 C7 C8 171.66(13) . . . . ?
Rh1 N1 C11 C10 -173.91(13) . . . . ?
Rh1 N1 C11 C11 3.91(12) . . . 8_565 ?
Rh1 C2 C3 C3 61.45(5) . . . 8_565 ?
Rh1 C2 C3 C6 -118.58(18) . . . . ?
N1 C7 C8 C9 1.0(3) . . . . ?
C1 C2 C3 Rh1 -83.02(14) . . . . ?
C1 C2 C3 C3 -21.57(16) . . . 8_565 ?
C1 C2 C3 C6 158.40(18) . . . . ?
C2 C1 C2 Rh1 -36.00(16) 8_565 . . . ?
C2 C1 C2 C3 31.9(2) 8_565 . . . ?
C2 C1 C2 C5 -171.37(11) 8_565 . . . ?
C4 C1 C2 Rh1 -158.34(16) . . . . ?
C4 C1 C2 C3 -90.4(2) . . . . ?
C4 C1 C2 C5 66.3(3) . . . . ?
C5 C2 C3 Rh1 121.51(18) . . . . ?
C5 C2 C3 C3 -177.04(15) . . . 8_565 ?
C5 C2 C3 C6 2.9(3) . . . . ?
C7 N1 C11 C10 -0.9(2) . . . . ?
C7 N1 C11 C11 176.90(12) . . . 8_565 ?
C7 C8 C9 C10 0.2(3) . . . . ?
C8 C9 C10 C11 -1.6(3) . . . . ?
C9 C10 C11 N1 2.0(3) . . . . ?
C9 C10 C11 C11 -175.60(13) . . . 8_565 ?
C11 N1 C7 C8 -0.6(3) . . . . ?

_shelx_SHELXL_version_number     2014/7
_olex2_submission_special_instructions 'No special instructions were received'
_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: dicloromethane/pentane'
_chemical_properties_physical    Air-sensitive
