# Electronic Supplementary Material (ESI) for New Journal of Chemistry.
# This journal is © The Royal Society of Chemistry and the Centre National de la Recherche Scientifique 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_14tnd1h
_database_code_depnum_ccdc_archive 'CCDC 1475336'
_audit_update_record             
;
2016-04-20 deposited with the CCDC.
2016-08-31 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C16 H19 B F4 N3 O Rh'
_chemical_formula_weight         459.06

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'
Rh Rh -1.1178 0.9187 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           Monoclinic
_symmetry_space_group_name_H-M   'P 21/c'

loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'

_cell_length_a                   11.3846(4)
_cell_length_b                   11.2191(4)
_cell_length_c                   13.1581(5)
_cell_angle_alpha                90.00
_cell_angle_beta                 91.2636(5)
_cell_angle_gamma                90.00
_cell_volume                     1680.21(11)
_cell_formula_units_Z            4
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    9939
_cell_measurement_theta_min      2.39
_cell_measurement_theta_max      28.28

_exptl_crystal_description       block
_exptl_crystal_colour            red
_exptl_crystal_size_max          0.32
_exptl_crystal_size_mid          0.19
_exptl_crystal_size_min          0.15
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.815
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             920
_exptl_absorpt_coefficient_mu    1.069
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.7261
_exptl_absorpt_correction_T_max  0.8561
_exptl_absorpt_process_details   SADABS

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            25889
_diffrn_reflns_av_R_equivalents  0.0277
_diffrn_reflns_av_sigmaI/netI    0.0180
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_theta_min         1.79
_diffrn_reflns_theta_max         28.29
_reflns_number_total             4177
_reflns_number_gt                3782
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'

_refine_special_details          
; 
 Refinement of F² against ALL reflections.  The weighted R-factor wR and 
 goodness of fit S are based on F², conventional R-factors R are based 
 on F, with F set to zero for negative F². The threshold expression of 
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is 
 not relevant to the choice of reflections for refinement.  R-factors based 
 on F² are statistically about twice as large as those based on F, and R- 
 factors based on ALL data will be even larger. 
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0204P)²+1.2593P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         4177
_refine_ls_number_parameters     266
_refine_ls_number_restraints     25
_refine_ls_R_factor_all          0.0237
_refine_ls_R_factor_gt           0.0204
_refine_ls_wR_factor_ref         0.0502
_refine_ls_wR_factor_gt          0.0482
_refine_ls_goodness_of_fit_ref   1.071
_refine_ls_restrained_S_all      1.082
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000

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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
Rh1 Rh 0.248206(11) 0.784260(11) 0.411031(10) 0.01498(5) Uani 1 1 d . . .
O1 O 0.38060(10) 0.66525(11) 0.36695(9) 0.0167(2) Uani 1 1 d . . .
N1 N 0.38974(12) 0.83465(13) 0.50142(11) 0.0167(3) Uani 1 1 d . . .
N2 N 0.48669(12) 0.76233(12) 0.48918(11) 0.0150(3) Uani 1 1 d . . .
N3 N 0.53173(13) 0.48483(13) 0.34624(11) 0.0166(3) Uani 1 1 d D . .
H3N H 0.4637(14) 0.4737(19) 0.3202(15) 0.020 Uiso 1 1 d D . .
C1 C 0.57467(15) 0.79470(16) 0.55612(13) 0.0192(3) Uani 1 1 d . . .
H1 H 0.6498 0.7584 0.5630 0.023 Uiso 1 1 calc R . .
C2 C 0.53477(16) 0.88839(16) 0.61100(13) 0.0219(4) Uani 1 1 d . . .
H2 H 0.5763 0.9307 0.6630 0.026 Uiso 1 1 calc R . .
C3 C 0.41928(16) 0.90993(16) 0.57508(13) 0.0198(3) Uani 1 1 d . . .
H3 H 0.3693 0.9704 0.6003 0.024 Uiso 1 1 calc R . .
C4 C 0.47401(14) 0.66937(15) 0.41823(12) 0.0147(3) Uani 1 1 d . . .
C5 C 0.56181(14) 0.57977(14) 0.40787(12) 0.0148(3) Uani 1 1 d . . .
C6 C 0.67658(15) 0.56009(16) 0.44322(14) 0.0197(3) Uani 1 1 d . . .
H6 H 0.7213 0.6107 0.4871 0.024 Uiso 1 1 calc R . .
C7 C 0.71332(16) 0.45225(16) 0.40208(14) 0.0214(4) Uani 1 1 d . . .
H7 H 0.7879 0.4159 0.4129 0.026 Uiso 1 1 calc R . .
C8 C 0.62154(15) 0.40755(16) 0.34247(13) 0.0188(3) Uani 1 1 d . . .
H8 H 0.6221 0.3349 0.3054 0.023 Uiso 1 1 calc R . .
C9 C 0.13014(15) 0.75589(16) 0.28407(13) 0.0198(3) Uani 1 1 d . . .
H9 H 0.1687 0.7252 0.2217 0.024 Uiso 1 1 calc R . .
C10 C 0.11159(15) 0.66946(16) 0.35837(14) 0.0204(3) Uani 1 1 d . . .
H10 H 0.1384 0.5877 0.3395 0.025 Uiso 1 1 calc R . .
C11 C 0.01051(15) 0.67161(17) 0.43141(14) 0.0230(4) Uani 1 1 d . . .
H11A H 0.0234 0.6091 0.4836 0.028 Uiso 1 1 calc R . .
H11B H -0.0632 0.6524 0.3936 0.028 Uiso 1 1 calc R . .
C12 C -0.00365(16) 0.79256(17) 0.48460(14) 0.0220(4) Uani 1 1 d . . .
H12A H -0.0614 0.8413 0.4455 0.026 Uiso 1 1 calc R . .
H12B H -0.0353 0.7793 0.5532 0.026 Uiso 1 1 calc R . .
C13 C 0.11139(15) 0.86124(16) 0.49472(13) 0.0191(3) Uani 1 1 d . . .
H13 H 0.1344 0.8815 0.5664 0.023 Uiso 1 1 calc R . .
C14 C 0.15119(15) 0.94347(15) 0.42289(13) 0.0189(3) Uani 1 1 d . . .
H14 H 0.1968 1.0115 0.4530 0.023 Uiso 1 1 calc R . .
C15 C 0.08977(16) 0.97251(16) 0.32245(14) 0.0220(4) Uani 1 1 d . . .
H15A H 0.1444 1.0175 0.2792 0.026 Uiso 1 1 calc R . .
H15B H 0.0212 1.0242 0.3353 0.026 Uiso 1 1 calc R . .
C16 C 0.04798(15) 0.86050(17) 0.26514(13) 0.0217(4) Uani 1 1 d . . .
H16A H -0.0318 0.8391 0.2873 0.026 Uiso 1 1 calc R . .
H16B H 0.0435 0.8777 0.1914 0.026 Uiso 1 1 calc R . .
B1 B 0.29280(18) 0.33649(19) 0.22528(16) 0.0219(4) Uani 1 1 d . . .
F1 F 0.41393(10) 0.32549(12) 0.20981(9) 0.0312(3) Uani 1 1 d . A .
F2 F 0.2472(6) 0.3589(10) 0.1289(5) 0.0347(14) Uani 0.57(3) 1 d PU A 1
F3 F 0.2461(13) 0.2326(11) 0.2605(10) 0.038(2) Uani 0.57(3) 1 d P A 1
F4 F 0.2808(9) 0.4271(11) 0.2896(12) 0.046(2) Uani 0.57(3) 1 d PU A 1
F2' F 0.2296(7) 0.3997(14) 0.1491(8) 0.0355(19) Uani 0.43(3) 1 d PU A 2
F3' F 0.2436(17) 0.2284(13) 0.2445(14) 0.036(3) Uani 0.43(3) 1 d P A 2
F4' F 0.2786(12) 0.4091(12) 0.3163(7) 0.0295(15) Uani 0.43(3) 1 d PU A 2


_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 N1 2.0606(14) . ?
Rh1 O1 2.1047(11) . ?
Rh1 C14 2.1076(16) . ?
Rh1 C13 2.1120(16) . ?
Rh1 C10 2.1237(17) . ?
Rh1 C9 2.1447(17) . ?
O1 C4 1.2476(19) . ?
N1 C3 1.323(2) . ?
N1 N2 1.3822(19) . ?
N2 C1 1.368(2) . ?
N2 C4 1.405(2) . ?
N3 C8 1.342(2) . ?
N3 C5 1.377(2) . ?
N3 H3N 0.849(15) . ?
C1 C2 1.359(2) . ?
C1 H1 0.9500 . ?
C2 C3 1.408(2) . ?
C2 H2 0.9500 . ?
C3 H3 0.9500 . ?
C4 C5 1.426(2) . ?
C5 C6 1.395(2) . ?
C6 C7 1.394(2) . ?
C6 H6 0.9500 . ?
C7 C8 1.386(3) . ?
C7 H7 0.9500 . ?
C8 H8 0.9500 . ?
C9 C10 1.396(3) . ?
C9 C16 1.518(3) . ?
C9 H9 1.0000 . ?
C10 C11 1.516(2) . ?
C10 H10 1.0000 . ?
C11 C12 1.537(3) . ?
C11 H11A 0.9900 . ?
C11 H11B 0.9900 . ?
C12 C13 1.523(2) . ?
C12 H12A 0.9900 . ?
C12 H12B 0.9900 . ?
C13 C14 1.403(2) . ?
C13 H13 1.0000 . ?
C14 C15 1.517(2) . ?
C14 H14 1.0000 . ?
C15 C16 1.536(3) . ?
C15 H15A 0.9900 . ?
C15 H15B 0.9900 . ?
C16 H16A 0.9900 . ?
C16 H16B 0.9900 . ?
B1 F4 1.332(10) . ?
B1 F3' 1.362(18) . ?
B1 F3 1.366(14) . ?
B1 F2 1.382(5) . ?
B1 F1 1.404(2) . ?
B1 F2' 1.413(7) . ?
B1 F4' 1.460(12) . ?

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 O1 77.14(5) . . ?
N1 Rh1 C14 97.42(6) . . ?
O1 Rh1 C14 159.66(6) . . ?
N1 Rh1 C13 99.39(6) . . ?
O1 Rh1 C13 160.74(6) . . ?
C14 Rh1 C13 38.84(7) . . ?
N1 Rh1 C10 155.84(6) . . ?
O1 Rh1 C10 92.82(6) . . ?
C14 Rh1 C10 99.03(7) . . ?
C13 Rh1 C10 82.81(7) . . ?
N1 Rh1 C9 163.53(6) . . ?
O1 Rh1 C9 97.56(6) . . ?
C14 Rh1 C9 82.12(7) . . ?
C13 Rh1 C9 90.58(7) . . ?
C10 Rh1 C9 38.19(7) . . ?
C4 O1 Rh1 115.75(11) . . ?
C3 N1 N2 105.62(13) . . ?
C3 N1 Rh1 141.32(12) . . ?
N2 N1 Rh1 112.83(10) . . ?
C1 N2 N1 110.14(13) . . ?
C1 N2 C4 133.46(14) . . ?
N1 N2 C4 116.26(13) . . ?
C8 N3 C5 109.97(14) . . ?
C8 N3 H3N 125.3(14) . . ?
C5 N3 H3N 124.4(14) . . ?
C2 C1 N2 107.38(15) . . ?
C2 C1 H1 126.3 . . ?
N2 C1 H1 126.3 . . ?
C1 C2 C3 105.96(15) . . ?
C1 C2 H2 127.0 . . ?
C3 C2 H2 127.0 . . ?
N1 C3 C2 110.89(15) . . ?
N1 C3 H3 124.6 . . ?
C2 C3 H3 124.6 . . ?
O1 C4 N2 117.44(14) . . ?
O1 C4 C5 120.86(15) . . ?
N2 C4 C5 121.64(14) . . ?
N3 C5 C6 107.02(14) . . ?
N3 C5 C4 115.83(14) . . ?
C6 C5 C4 137.14(16) . . ?
C7 C6 C5 107.15(15) . . ?
C7 C6 H6 126.4 . . ?
C5 C6 H6 126.4 . . ?
C8 C7 C6 107.75(15) . . ?
C8 C7 H7 126.1 . . ?
C6 C7 H7 126.1 . . ?
N3 C8 C7 108.10(15) . . ?
N3 C8 H8 126.0 . . ?
C7 C8 H8 126.0 . . ?
C10 C9 C16 123.35(16) . . ?
C10 C9 Rh1 70.10(10) . . ?
C16 C9 Rh1 112.73(12) . . ?
C10 C9 H9 114.3 . . ?
C16 C9 H9 114.3 . . ?
Rh1 C9 H9 114.3 . . ?
C9 C10 C11 124.16(16) . . ?
C9 C10 Rh1 71.72(10) . . ?
C11 C10 Rh1 110.14(12) . . ?
C9 C10 H10 114.3 . . ?
C11 C10 H10 114.3 . . ?
Rh1 C10 H10 114.3 . . ?
C10 C11 C12 113.05(15) . . ?
C10 C11 H11A 109.0 . . ?
C12 C11 H11A 109.0 . . ?
C10 C11 H11B 109.0 . . ?
C12 C11 H11B 109.0 . . ?
H11A C11 H11B 107.8 . . ?
C13 C12 C11 112.83(14) . . ?
C13 C12 H12A 109.0 . . ?
C11 C12 H12A 109.0 . . ?
C13 C12 H12B 109.0 . . ?
C11 C12 H12B 109.0 . . ?
H12A C12 H12B 107.8 . . ?
C14 C13 C12 124.31(15) . . ?
C14 C13 Rh1 70.41(10) . . ?
C12 C13 Rh1 112.97(12) . . ?
C14 C13 H13 113.9 . . ?
C12 C13 H13 113.9 . . ?
Rh1 C13 H13 113.9 . . ?
C13 C14 C15 125.35(16) . . ?
C13 C14 Rh1 70.75(10) . . ?
C15 C14 Rh1 110.48(11) . . ?
C13 C14 H14 114.0 . . ?
C15 C14 H14 114.0 . . ?
Rh1 C14 H14 114.0 . . ?
C14 C15 C16 112.57(15) . . ?
C14 C15 H15A 109.1 . . ?
C16 C15 H15A 109.1 . . ?
C14 C15 H15B 109.1 . . ?
C16 C15 H15B 109.1 . . ?
H15A C15 H15B 107.8 . . ?
C9 C16 C15 111.65(14) . . ?
C9 C16 H16A 109.3 . . ?
C15 C16 H16A 109.3 . . ?
C9 C16 H16B 109.3 . . ?
C15 C16 H16B 109.3 . . ?
H16A C16 H16B 108.0 . . ?
F4 B1 F3 112.9(7) . . ?
F4 B1 F2 113.8(4) . . ?
F3 B1 F2 109.0(6) . . ?
F4 B1 F1 105.9(5) . . ?
F3 B1 F1 111.4(6) . . ?
F2 B1 F1 103.5(4) . . ?
F3' B1 F1 111.0(7) . . ?
F3' B1 F2' 111.9(8) . . ?
F1 B1 F2' 115.3(4) . . ?
F3' B1 F4' 106.9(8) . . ?
F1 B1 F4' 107.1(6) . . ?
F2' B1 F4' 103.8(8) . . ?

_diffrn_measured_fraction_theta_max 1.000
_diffrn_reflns_theta_full        28.29
_diffrn_measured_fraction_theta_full 1.000
_refine_diff_density_max         0.398
_refine_diff_density_min         -0.353
_refine_diff_density_rms         0.064
####################################################################### 
# 
# 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_14tnd2h
_database_code_depnum_ccdc_archive 'CCDC 1475337'
_audit_update_record             
;
2016-04-20 deposited with the CCDC.
2016-08-31 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C16 H18 N3 O Rh'
_chemical_formula_weight         371.24

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'
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'
Rh Rh -1.1178 0.9187 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           Monoclinic
_symmetry_space_group_name_H-M   'P 21/n'

loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -y-1/2, z-1/2'

_cell_length_a                   10.9656(5)
_cell_length_b                   10.4739(5)
_cell_length_c                   13.1256(6)
_cell_angle_alpha                90.00
_cell_angle_beta                 113.9866(6)
_cell_angle_gamma                90.00
_cell_volume                     1377.32(11)
_cell_formula_units_Z            4
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    9859
_cell_measurement_theta_min      2.58
_cell_measurement_theta_max      28.30

_exptl_crystal_description       block
_exptl_crystal_colour            yellow
_exptl_crystal_size_max          0.48
_exptl_crystal_size_mid          0.30
_exptl_crystal_size_min          0.15
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.790
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             752
_exptl_absorpt_coefficient_mu    1.242
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.5870
_exptl_absorpt_correction_T_max  0.8356
_exptl_absorpt_process_details   SADABS

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            28540
_diffrn_reflns_av_R_equivalents  0.0185
_diffrn_reflns_av_sigmaI/netI    0.0094
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_theta_min         2.05
_diffrn_reflns_theta_max         28.31
_reflns_number_total             3422
_reflns_number_gt                3321
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'

_refine_special_details          
; 
 Refinement of F² against ALL reflections.  The weighted R-factor wR and 
 goodness of fit S are based on F², conventional R-factors R are based 
 on F, with F set to zero for negative F². The threshold expression of 
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is 
 not relevant to the choice of reflections for refinement.  R-factors based 
 on F² are statistically about twice as large as those based on F, and R- 
 factors based on ALL data will be even larger. 
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0167P)²+1.4393P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         3422
_refine_ls_number_parameters     190
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0172
_refine_ls_R_factor_gt           0.0167
_refine_ls_wR_factor_ref         0.0415
_refine_ls_wR_factor_gt          0.0412
_refine_ls_goodness_of_fit_ref   1.060
_refine_ls_restrained_S_all      1.060
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000

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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
Rh1 Rh 0.309849(10) 0.163955(10) 0.497231(8) 0.01045(4) Uani 1 1 d . . .
O1 O 0.47806(12) 0.09968(12) 0.21948(10) 0.0237(2) Uani 1 1 d . . .
N1 N 0.49610(12) 0.18273(12) 0.48811(10) 0.0131(2) Uani 1 1 d . . .
N2 N 0.52543(12) 0.15386(12) 0.39835(10) 0.0144(2) Uani 1 1 d . . .
N3 N 0.24920(12) 0.05707(12) 0.35289(10) 0.0144(2) Uani 1 1 d . . .
C1 C 0.65196(15) 0.19231(15) 0.41748(13) 0.0171(3) Uani 1 1 d . . .
H1 H 0.6944 0.1830 0.3676 0.020 Uiso 1 1 calc R . .
C2 C 0.70649(15) 0.24642(16) 0.52099(13) 0.0186(3) Uani 1 1 d . . .
H2 H 0.7933 0.2817 0.5576 0.022 Uiso 1 1 calc R . .
C3 C 0.60644(14) 0.23862(15) 0.56144(12) 0.0166(3) Uani 1 1 d . . .
H3 H 0.6159 0.2693 0.6324 0.020 Uiso 1 1 calc R . .
C4 C 0.43695(15) 0.09991(14) 0.29346(12) 0.0155(3) Uani 1 1 d . . .
C5 C 0.31144(14) 0.04706(14) 0.28018(12) 0.0139(3) Uani 1 1 d . . .
C6 C 0.23213(16) -0.02434(15) 0.18632(13) 0.0196(3) Uani 1 1 d . . .
H6 H 0.2521 -0.0446 0.1242 0.023 Uiso 1 1 calc R . .
C7 C 0.11927(16) -0.05962(15) 0.20143(13) 0.0201(3) Uani 1 1 d . . .
H7 H 0.0467 -0.1092 0.1522 0.024 Uiso 1 1 calc R . .
C8 C 0.13338(15) -0.00765(15) 0.30362(13) 0.0185(3) Uani 1 1 d . . .
H8 H 0.0693 -0.0167 0.3347 0.022 Uiso 1 1 calc R . .
C9 C 0.10835(14) 0.21085(14) 0.46267(12) 0.0140(3) Uani 1 1 d . . .
H9 H 0.0439 0.1881 0.3855 0.017 Uiso 1 1 calc R . .
C10 C 0.14645(14) 0.10733(14) 0.53669(12) 0.0149(3) Uani 1 1 d . . .
H10 H 0.1046 0.0243 0.5027 0.018 Uiso 1 1 calc R . .
C11 C 0.17247(15) 0.12149(16) 0.65917(12) 0.0176(3) Uani 1 1 d . . .
H11A H 0.1441 0.0426 0.6849 0.021 Uiso 1 1 calc R . .
H11B H 0.1184 0.1931 0.6677 0.021 Uiso 1 1 calc R . .
C12 C 0.32045(15) 0.14658(15) 0.73213(12) 0.0171(3) Uani 1 1 d . . .
H12A H 0.3276 0.1997 0.7967 0.020 Uiso 1 1 calc R . .
H12B H 0.3654 0.0642 0.7612 0.020 Uiso 1 1 calc R . .
C13 C 0.39171(14) 0.21328(15) 0.66971(11) 0.0145(3) Uani 1 1 d . . .
H13 H 0.4912 0.2066 0.7068 0.017 Uiso 1 1 calc R . .
C14 C 0.34584(15) 0.32433(14) 0.60633(12) 0.0146(3) Uani 1 1 d . . .
H14 H 0.4183 0.3825 0.6066 0.018 Uiso 1 1 calc R . .
C15 C 0.21914(15) 0.39270(15) 0.59685(12) 0.0174(3) Uani 1 1 d . . .
H15A H 0.2302 0.4856 0.5896 0.021 Uiso 1 1 calc R . .
H15B H 0.2056 0.3785 0.6661 0.021 Uiso 1 1 calc R . .
C16 C 0.09462(15) 0.34656(14) 0.49650(13) 0.0164(3) Uani 1 1 d . . .
H16A H 0.0161 0.3518 0.5155 0.020 Uiso 1 1 calc R . .
H16B H 0.0784 0.4040 0.4324 0.020 Uiso 1 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 N3 2.0641(12) . ?
Rh1 N1 2.1031(12) . ?
Rh1 C9 2.1247(14) . ?
Rh1 C13 2.1321(14) . ?
Rh1 C14 2.1374(14) . ?
Rh1 C10 2.1413(14) . ?
O1 C4 1.2256(18) . ?
N1 C3 1.3364(19) . ?
N1 N2 1.3752(17) . ?
N2 C1 1.3664(19) . ?
N2 C4 1.4387(19) . ?
N3 C8 1.3501(19) . ?
N3 C5 1.3847(18) . ?
C1 C2 1.365(2) . ?
C1 H1 0.9500 . ?
C2 C3 1.402(2) . ?
C2 H2 0.9500 . ?
C3 H3 0.9500 . ?
C4 C5 1.427(2) . ?
C5 C6 1.401(2) . ?
C6 C7 1.381(2) . ?
C6 H6 0.9500 . ?
C7 C8 1.397(2) . ?
C7 H7 0.9500 . ?
C8 H8 0.9500 . ?
C9 C10 1.402(2) . ?
C9 C16 1.515(2) . ?
C9 H9 1.0000 . ?
C10 C11 1.522(2) . ?
C10 H10 1.0000 . ?
C11 C12 1.535(2) . ?
C11 H11A 0.9900 . ?
C11 H11B 0.9900 . ?
C12 C13 1.513(2) . ?
C12 H12A 0.9900 . ?
C12 H12B 0.9900 . ?
C13 C14 1.399(2) . ?
C13 H13 1.0000 . ?
C14 C15 1.522(2) . ?
C14 H14 1.0000 . ?
C15 C16 1.540(2) . ?
C15 H15A 0.9900 . ?
C15 H15B 0.9900 . ?
C16 H16A 0.9900 . ?
C16 H16B 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
N3 Rh1 N1 87.51(5) . . ?
N3 Rh1 C9 90.59(5) . . ?
N1 Rh1 C9 156.34(5) . . ?
N3 Rh1 C13 161.00(5) . . ?
N1 Rh1 C13 92.20(5) . . ?
C9 Rh1 C13 97.07(5) . . ?
N3 Rh1 C14 160.74(5) . . ?
N1 Rh1 C14 92.61(5) . . ?
C9 Rh1 C14 81.61(6) . . ?
C13 Rh1 C14 38.26(6) . . ?
N3 Rh1 C10 94.74(5) . . ?
N1 Rh1 C10 165.27(5) . . ?
C9 Rh1 C10 38.36(5) . . ?
C13 Rh1 C10 80.96(5) . . ?
C14 Rh1 C10 90.02(6) . . ?
C3 N1 N2 104.76(12) . . ?
C3 N1 Rh1 128.01(10) . . ?
N2 N1 Rh1 126.79(9) . . ?
C1 N2 N1 110.57(12) . . ?
C1 N2 C4 122.07(12) . . ?
N1 N2 C4 127.20(12) . . ?
C8 N3 C5 105.25(12) . . ?
C8 N3 Rh1 126.97(10) . . ?
C5 N3 Rh1 127.48(10) . . ?
C2 C1 N2 107.85(13) . . ?
C2 C1 H1 126.1 . . ?
N2 C1 H1 126.1 . . ?
C1 C2 C3 105.01(13) . . ?
C1 C2 H2 127.5 . . ?
C3 C2 H2 127.5 . . ?
N1 C3 C2 111.81(13) . . ?
N1 C3 H3 124.1 . . ?
C2 C3 H3 124.1 . . ?
O1 C4 C5 123.34(14) . . ?
O1 C4 N2 115.90(13) . . ?
C5 C4 N2 120.73(13) . . ?
N3 C5 C6 110.05(13) . . ?
N3 C5 C4 127.42(13) . . ?
C6 C5 C4 122.53(14) . . ?
C7 C6 C5 106.79(14) . . ?
C7 C6 H6 126.6 . . ?
C5 C6 H6 126.6 . . ?
C6 C7 C8 106.13(13) . . ?
C6 C7 H7 126.9 . . ?
C8 C7 H7 126.9 . . ?
N3 C8 C7 111.79(14) . . ?
N3 C8 H8 124.1 . . ?
C7 C8 H8 124.1 . . ?
C10 C9 C16 124.05(13) . . ?
C10 C9 Rh1 71.46(8) . . ?
C16 C9 Rh1 111.90(10) . . ?
C10 C9 H9 114.0 . . ?
C16 C9 H9 114.0 . . ?
Rh1 C9 H9 114.0 . . ?
C9 C10 C11 122.15(14) . . ?
C9 C10 Rh1 70.18(8) . . ?
C11 C10 Rh1 114.37(9) . . ?
C9 C10 H10 114.2 . . ?
C11 C10 H10 114.2 . . ?
Rh1 C10 H10 114.2 . . ?
C10 C11 C12 111.87(12) . . ?
C10 C11 H11A 109.2 . . ?
C12 C11 H11A 109.2 . . ?
C10 C11 H11B 109.2 . . ?
C12 C11 H11B 109.2 . . ?
H11A C11 H11B 107.9 . . ?
C13 C12 C11 112.89(12) . . ?
C13 C12 H12A 109.0 . . ?
C11 C12 H12A 109.0 . . ?
C13 C12 H12B 109.0 . . ?
C11 C12 H12B 109.0 . . ?
H12A C12 H12B 107.8 . . ?
C14 C13 C12 124.45(13) . . ?
C14 C13 Rh1 71.07(8) . . ?
C12 C13 Rh1 112.07(10) . . ?
C14 C13 H13 113.9 . . ?
C12 C13 H13 113.9 . . ?
Rh1 C13 H13 113.9 . . ?
C13 C14 C15 122.35(13) . . ?
C13 C14 Rh1 70.66(8) . . ?
C15 C14 Rh1 113.64(10) . . ?
C13 C14 H14 114.3 . . ?
C15 C14 H14 114.3 . . ?
Rh1 C14 H14 114.3 . . ?
C14 C15 C16 112.63(12) . . ?
C14 C15 H15A 109.1 . . ?
C16 C15 H15A 109.1 . . ?
C14 C15 H15B 109.1 . . ?
C16 C15 H15B 109.1 . . ?
H15A C15 H15B 107.8 . . ?
C9 C16 C15 112.71(12) . . ?
C9 C16 H16A 109.1 . . ?
C15 C16 H16A 109.1 . . ?
C9 C16 H16B 109.1 . . ?
C15 C16 H16B 109.1 . . ?
H16A C16 H16B 107.8 . . ?

_diffrn_measured_fraction_theta_max 1.000
_diffrn_reflns_theta_full        28.31
_diffrn_measured_fraction_theta_full 1.000
_refine_diff_density_max         0.433
_refine_diff_density_min         -0.385
_refine_diff_density_rms         0.061
