# Electronic Supplementary Material (ESI) for Organic Chemistry Frontiers.
# This journal is © the Partner Organisations 2017

####################################################################### 
# 
# 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_1
_database_code_depnum_ccdc_archive 'CCDC 1563728'
_audit_update_record             
;
2017-07-21 deposited with the CCDC.
2017-10-13 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C3.80 H2.80 Br0.20 N0.20 O0.40'
_chemical_formula_weight         73.64

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'
Br Br -0.2901 2.4595 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           Monoclinic
_symmetry_space_group_name_H-M   P2(1)/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                   17.1209(10)
_cell_length_b                   6.8257(5)
_cell_length_c                   14.2218(10)
_cell_angle_alpha                90.00
_cell_angle_beta                 100.200(3)
_cell_angle_gamma                90.00
_cell_volume                     1635.72(19)
_cell_formula_units_Z            20
_cell_measurement_temperature    150(2)
_cell_measurement_reflns_used    4800
_cell_measurement_theta_min      2.91
_cell_measurement_theta_max      26.30

_exptl_crystal_description       Prism
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.35
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.20
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.495
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             744
_exptl_absorpt_coefficient_mu    2.522
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.4723
_exptl_absorpt_correction_T_max  0.6325
_exptl_absorpt_process_details   sadabs

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      150(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            12488
_diffrn_reflns_av_R_equivalents  0.0370
_diffrn_reflns_av_sigmaI/netI    0.0342
_diffrn_reflns_limit_h_min       -21
_diffrn_reflns_limit_h_max       21
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_theta_min         2.91
_diffrn_reflns_theta_max         26.38
_reflns_number_total             3326
_reflns_number_gt                2711
_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)+(0.0508P)²+0.6263P] 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         3326
_refine_ls_number_parameters     209
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0480
_refine_ls_R_factor_gt           0.0357
_refine_ls_wR_factor_ref         0.0987
_refine_ls_wR_factor_gt          0.0917
_refine_ls_goodness_of_fit_ref   1.016
_refine_ls_restrained_S_all      1.016
_refine_ls_shift/su_max          0.014
_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
Br1 Br 1.128246(17) 0.35673(5) 0.44244(2) 0.06469(14) Uani 1 1 d . . .
O1 O 0.76596(9) -0.0456(2) 0.28969(11) 0.0405(4) Uani 1 1 d . . .
O2 O 0.83766(11) -0.3212(3) 0.28565(15) 0.0562(5) Uani 1 1 d . . .
C7 C 0.83487(13) -0.1493(3) 0.30074(15) 0.0380(5) Uani 1 1 d . . .
C14 C 0.65615(12) -0.0850(3) 0.16071(16) 0.0370(5) Uani 1 1 d . . .
C15 C 0.68482(12) 0.0800(3) 0.10736(15) 0.0343(4) Uani 1 1 d . . .
C8 C 0.69530(13) -0.1432(3) 0.25040(16) 0.0373(5) Uani 1 1 d . . .
N1 N 0.68764(12) 0.0496(3) 0.01523(13) 0.0457(5) Uani 1 1 d . . .
C4 C 0.90402(13) -0.0213(3) 0.33436(15) 0.0376(5) Uani 1 1 d . . .
C12 C 0.58629(14) -0.1841(4) 0.12280(19) 0.0479(6) Uani 1 1 d . . .
H12 H 0.5593 -0.1502 0.0607 0.057 Uiso 1 1 calc R . .
C9 C 0.66523(15) -0.2864(4) 0.30284(18) 0.0468(5) Uani 1 1 d . . .
H9 H 0.6922 -0.3211 0.3648 0.056 Uiso 1 1 calc R . .
C16 C 0.70485(15) 0.2589(3) 0.15161(17) 0.0442(5) Uani 1 1 d . . .
H16 H 0.7020 0.2765 0.2172 0.053 Uiso 1 1 calc R . .
C2 C 1.04558(15) 0.0056(4) 0.3825(2) 0.0544(6) Uani 1 1 d . . .
H2 H 1.0968 -0.0529 0.3936 0.065 Uiso 1 1 calc R . .
C3 C 0.97942(15) -0.1057(4) 0.3505(2) 0.0501(6) Uani 1 1 d . . .
H3 H 0.9850 -0.2417 0.3393 0.060 Uiso 1 1 calc R . .
C5 C 0.89701(15) 0.1777(4) 0.3493(2) 0.0498(6) Uani 1 1 d . . .
H5 H 0.8461 0.2376 0.3373 0.060 Uiso 1 1 calc R . .
C10 C 0.59546(16) -0.3776(4) 0.2634(2) 0.0550(7) Uani 1 1 d . . .
H10 H 0.5743 -0.4758 0.2991 0.066 Uiso 1 1 calc R . .
C1 C 1.03696(14) 0.2027(4) 0.39810(17) 0.0455(5) Uani 1 1 d . . .
C11 C 0.55511(15) -0.3296(4) 0.1726(2) 0.0557(7) Uani 1 1 d . . .
C19 C 0.71224(17) 0.1987(4) -0.03278(18) 0.0552(6) Uani 1 1 d . . .
H19 H 0.7154 0.1783 -0.0981 0.066 Uiso 1 1 calc R . .
C17 C 0.72890(16) 0.4105(4) 0.09970(19) 0.0502(6) Uani 1 1 d . . .
H17 H 0.7422 0.5343 0.1287 0.060 Uiso 1 1 calc R . .
C18 C 0.73334(16) 0.3803(4) 0.00601(19) 0.0517(6) Uani 1 1 d . . .
H18 H 0.7505 0.4814 -0.0315 0.062 Uiso 1 1 calc R . .
C6 C 0.96365(16) 0.2902(4) 0.3818(2) 0.0555(6) Uani 1 1 d . . .
H6 H 0.9587 0.4265 0.3927 0.067 Uiso 1 1 calc R . .
C13 C 0.4793(2) -0.4333(6) 0.1301(3) 0.0932(12) Uani 1 1 d . . .
H13A H 0.4516 -0.3582 0.0755 0.140 Uiso 1 1 calc R . .
H13B H 0.4452 -0.4447 0.1784 0.140 Uiso 1 1 calc R . .
H13C H 0.4917 -0.5643 0.1088 0.140 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
Br1 C1 1.897(2) . ?
O1 C7 1.361(3) . ?
O1 C8 1.407(3) . ?
O2 C7 1.195(3) . ?
C7 C4 1.481(3) . ?
C14 C8 1.390(3) . ?
C14 C12 1.396(3) . ?
C14 C15 1.489(3) . ?
C15 N1 1.336(3) . ?
C15 C16 1.389(3) . ?
C8 C9 1.383(3) . ?
N1 C19 1.335(3) . ?
C4 C5 1.383(3) . ?
C4 C3 1.395(3) . ?
C12 C11 1.381(4) . ?
C12 H12 0.9500 . ?
C9 C10 1.375(4) . ?
C9 H9 0.9500 . ?
C16 C17 1.376(3) . ?
C16 H16 0.9500 . ?
C2 C3 1.372(4) . ?
C2 C1 1.376(4) . ?
C2 H2 0.9500 . ?
C3 H3 0.9500 . ?
C5 C6 1.385(4) . ?
C5 H5 0.9500 . ?
C10 C11 1.392(4) . ?
C10 H10 0.9500 . ?
C1 C6 1.372(4) . ?
C11 C13 1.508(4) . ?
C19 C18 1.379(4) . ?
C19 H19 0.9500 . ?
C17 C18 1.364(4) . ?
C17 H17 0.9500 . ?
C18 H18 0.9500 . ?
C6 H6 0.9500 . ?
C13 H13A 0.9800 . ?
C13 H13B 0.9800 . ?
C13 H13C 0.9800 . ?

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
C7 O1 C8 117.78(17) . . ?
O2 C7 O1 123.5(2) . . ?
O2 C7 C4 125.6(2) . . ?
O1 C7 C4 110.93(18) . . ?
C8 C14 C12 117.2(2) . . ?
C8 C14 C15 122.3(2) . . ?
C12 C14 C15 120.4(2) . . ?
N1 C15 C16 122.2(2) . . ?
N1 C15 C14 117.02(19) . . ?
C16 C15 C14 120.77(19) . . ?
C9 C8 C14 122.1(2) . . ?
C9 C8 O1 119.8(2) . . ?
C14 C8 O1 118.04(19) . . ?
C19 N1 C15 116.9(2) . . ?
C5 C4 C3 118.9(2) . . ?
C5 C4 C7 122.9(2) . . ?
C3 C4 C7 118.2(2) . . ?
C11 C12 C14 122.2(2) . . ?
C11 C12 H12 118.9 . . ?
C14 C12 H12 118.9 . . ?
C10 C9 C8 118.7(2) . . ?
C10 C9 H9 120.7 . . ?
C8 C9 H9 120.7 . . ?
C17 C16 C15 119.4(2) . . ?
C17 C16 H16 120.3 . . ?
C15 C16 H16 120.3 . . ?
C3 C2 C1 119.2(2) . . ?
C3 C2 H2 120.4 . . ?
C1 C2 H2 120.4 . . ?
C2 C3 C4 120.8(2) . . ?
C2 C3 H3 119.6 . . ?
C4 C3 H3 119.6 . . ?
C4 C5 C6 120.5(2) . . ?
C4 C5 H5 119.8 . . ?
C6 C5 H5 119.8 . . ?
C9 C10 C11 121.6(2) . . ?
C9 C10 H10 119.2 . . ?
C11 C10 H10 119.2 . . ?
C6 C1 C2 121.3(2) . . ?
C6 C1 Br1 119.4(2) . . ?
C2 C1 Br1 119.35(19) . . ?
C12 C11 C10 118.2(2) . . ?
C12 C11 C13 121.0(3) . . ?
C10 C11 C13 120.8(3) . . ?
N1 C19 C18 124.4(2) . . ?
N1 C19 H19 117.8 . . ?
C18 C19 H19 117.8 . . ?
C18 C17 C16 118.9(2) . . ?
C18 C17 H17 120.5 . . ?
C16 C17 H17 120.5 . . ?
C17 C18 C19 118.1(2) . . ?
C17 C18 H18 120.9 . . ?
C19 C18 H18 120.9 . . ?
C1 C6 C5 119.3(2) . . ?
C1 C6 H6 120.3 . . ?
C5 C6 H6 120.3 . . ?
C11 C13 H13A 109.5 . . ?
C11 C13 H13B 109.5 . . ?
H13A C13 H13B 109.5 . . ?
C11 C13 H13C 109.5 . . ?
H13A C13 H13C 109.5 . . ?
H13B C13 H13C 109.5 . . ?

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
C8 O1 C7 O2 -5.8(3) . . . . ?
C8 O1 C7 C4 174.78(17) . . . . ?
C8 C14 C15 N1 133.4(2) . . . . ?
C12 C14 C15 N1 -48.7(3) . . . . ?
C8 C14 C15 C16 -48.7(3) . . . . ?
C12 C14 C15 C16 129.1(2) . . . . ?
C12 C14 C8 C9 -3.0(3) . . . . ?
C15 C14 C8 C9 174.9(2) . . . . ?
C12 C14 C8 O1 179.80(19) . . . . ?
C15 C14 C8 O1 -2.3(3) . . . . ?
C7 O1 C8 C9 69.9(3) . . . . ?
C7 O1 C8 C14 -112.8(2) . . . . ?
C16 C15 N1 C19 1.2(3) . . . . ?
C14 C15 N1 C19 179.0(2) . . . . ?
O2 C7 C4 C5 179.1(2) . . . . ?
O1 C7 C4 C5 -1.5(3) . . . . ?
O2 C7 C4 C3 -0.2(4) . . . . ?
O1 C7 C4 C3 179.2(2) . . . . ?
C8 C14 C12 C11 2.1(4) . . . . ?
C15 C14 C12 C11 -175.9(2) . . . . ?
C14 C8 C9 C10 1.9(3) . . . . ?
O1 C8 C9 C10 179.0(2) . . . . ?
N1 C15 C16 C17 -0.4(4) . . . . ?
C14 C15 C16 C17 -178.1(2) . . . . ?
C1 C2 C3 C4 -0.3(4) . . . . ?
C5 C4 C3 C2 1.2(4) . . . . ?
C7 C4 C3 C2 -179.5(2) . . . . ?
C3 C4 C5 C6 -1.4(4) . . . . ?
C7 C4 C5 C6 179.3(2) . . . . ?
C8 C9 C10 C11 0.2(4) . . . . ?
C3 C2 C1 C6 -0.4(4) . . . . ?
C3 C2 C1 Br1 179.9(2) . . . . ?
C14 C12 C11 C10 -0.1(4) . . . . ?
C14 C12 C11 C13 179.6(3) . . . . ?
C9 C10 C11 C12 -1.1(4) . . . . ?
C9 C10 C11 C13 179.2(3) . . . . ?
C15 N1 C19 C18 -1.1(4) . . . . ?
C15 C16 C17 C18 -0.8(4) . . . . ?
C16 C17 C18 C19 0.9(4) . . . . ?
N1 C19 C18 C17 0.0(4) . . . . ?
C2 C1 C6 C5 0.2(4) . . . . ?
Br1 C1 C6 C5 179.9(2) . . . . ?
C4 C5 C6 C1 0.7(4) . . . . ?

_diffrn_measured_fraction_theta_max 0.989
_diffrn_reflns_theta_full        26.38
_diffrn_measured_fraction_theta_full 0.989
_refine_diff_density_max         0.332
_refine_diff_density_min         -0.708
_refine_diff_density_rms         0.049
####################################################################### 
# 
# 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_1_CCDC1
_database_code_depnum_ccdc_archive 'CCDC 1563730'
_audit_update_record             
;
2017-07-21 deposited with the CCDC.
2017-10-13 downloaded from the CCDC.
;
# start Validation Reply Form
_vrf_PLAT029_1                   
;
PROBLEM: _diffrn_measured_fraction_theta_full value Low .      0.917 Note
RESPONSE: The data was collected on synchron radiation(BSRF) and the theta-max collected was restricted.
;
# Added during the CSD deposition process: Friday 21 July 2017 09:17 AM
# end Validation Reply Form


_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C24 H28 N O2 Rh'
_chemical_formula_sum            'C24 H28 N O2 Rh'
_chemical_formula_weight         465.38

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'
N N 0.0061 0.0033 '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           Triclinic
_symmetry_space_group_name_H-M   P-1
_symmetry_space_group_name_Hall  '-P 1'


loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   8.5810(17)
_cell_length_b                   10.888(2)
_cell_length_c                   11.352(2)
_cell_angle_alpha                93.19(3)
_cell_angle_beta                 106.92(3)
_cell_angle_gamma                90.49(3)
_cell_volume                     1012.8(3)
_cell_formula_units_Z            2
_cell_measurement_temperature    194(2)
_cell_measurement_reflns_used    13785
_cell_measurement_theta_min      0.41
_cell_measurement_theta_max      29.9

_exptl_crystal_description       prism
_exptl_crystal_colour            red
_exptl_crystal_size_max          0.15
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.10
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.526
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             480
_exptl_absorpt_coefficient_mu    0.863
_exptl_absorpt_correction_type   ?
_exptl_absorpt_correction_T_min  0.8815
_exptl_absorpt_correction_T_max  0.9187
_exptl_absorpt_process_details   ?

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      194(2)
_diffrn_radiation_wavelength     0.72010
_diffrn_radiation_type           ?
_diffrn_radiation_source         ?
_diffrn_radiation_monochromator  ?
_diffrn_measurement_device_type  marccd
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            3146
_diffrn_reflns_av_R_equivalents  0.0000
_diffrn_reflns_av_sigmaI/netI    0.0405
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       0
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_theta_min         1.90
_diffrn_reflns_theta_max         25.00
_reflns_number_total             3146
_reflns_number_gt                2833
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    ?
_computing_publication_material  ?

_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)+(0.1548P)²+0.0000P] 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         3146
_refine_ls_number_parameters     260
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0697
_refine_ls_R_factor_gt           0.0601
_refine_ls_wR_factor_ref         0.1888
_refine_ls_wR_factor_gt          0.1666
_refine_ls_goodness_of_fit_ref   1.105
_refine_ls_restrained_S_all      1.105
_refine_ls_shift/su_max          0.000
_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
C1 C -0.0352(9) 0.1688(6) 0.2673(6) 0.0135(14) Uani 1 1 d . . .
H1 H 0.0272 0.1871 0.3506 0.016 Uiso 1 1 calc R . .
C2 C -0.1906(9) 0.1201(6) 0.2439(6) 0.0151(14) Uani 1 1 d . . .
H2 H -0.2363 0.1082 0.3093 0.018 Uiso 1 1 calc R . .
C3 C -0.2805(9) 0.0882(6) 0.1200(6) 0.0185(15) Uani 1 1 d . . .
H3 H -0.3880 0.0542 0.1006 0.022 Uiso 1 1 calc R . .
C4 C -0.2094(8) 0.1075(6) 0.0284(6) 0.0166(15) Uani 1 1 d . . .
H4 H -0.2675 0.0851 -0.0550 0.020 Uiso 1 1 calc R . .
C5 C -0.0514(8) 0.1601(5) 0.0569(6) 0.0114(14) Uani 1 1 d . . .
C6 C 0.0399(8) 0.1839(5) -0.0306(6) 0.0132(14) Uani 1 1 d . . .
C7 C 0.1947(8) 0.2419(6) 0.0201(6) 0.0111(14) Uani 1 1 d . . .
C8 C 0.2886(9) 0.2645(6) -0.0611(6) 0.0156(15) Uani 1 1 d . . .
H8 H 0.3942 0.3018 -0.0298 0.019 Uiso 1 1 calc R . .
C9 C 0.2254(8) 0.2316(5) -0.1877(6) 0.0138(15) Uani 1 1 d . . .
H9 H 0.2898 0.2474 -0.2408 0.017 Uiso 1 1 calc R . .
C10 C 0.0719(9) 0.1768(5) -0.2375(5) 0.0134(14) Uani 1 1 d . . .
C11 C -0.0190(8) 0.1522(6) -0.1574(6) 0.0154(15) Uani 1 1 d . . .
H11 H -0.1233 0.1130 -0.1895 0.018 Uiso 1 1 calc R . .
C12 C 0.0053(9) 0.1434(6) -0.3750(6) 0.0176(15) Uani 1 1 d . . .
H12A H -0.0282 0.2182 -0.4189 0.026 Uiso 1 1 calc R . .
H12B H -0.0888 0.0868 -0.3902 0.026 Uiso 1 1 calc R . .
H12C H 0.0900 0.1036 -0.4046 0.026 Uiso 1 1 calc R . .
C13 C 0.4505(8) 0.4240(6) 0.2458(5) 0.0113(14) Uani 1 1 d . . .
C14 C 0.2954(8) 0.4783(5) 0.2013(6) 0.0112(13) Uani 1 1 d . . .
C15 C 0.2049(8) 0.4546(6) 0.2885(6) 0.0128(14) Uani 1 1 d . . .
C16 C 0.3107(8) 0.3926(6) 0.3896(5) 0.0109(14) Uani 1 1 d . . .
C17 C 0.4585(8) 0.3735(6) 0.3626(6) 0.0121(14) Uani 1 1 d . . .
C18 C 0.5894(8) 0.4330(6) 0.1906(6) 0.0145(14) Uani 1 1 d . . .
H18A H 0.6663 0.4985 0.2358 0.022 Uiso 1 1 calc R . .
H18B H 0.5471 0.4520 0.1038 0.022 Uiso 1 1 calc R . .
H18C H 0.6453 0.3545 0.1961 0.022 Uiso 1 1 calc R . .
C19 C 0.2399(9) 0.5552(6) 0.0917(6) 0.0192(16) Uani 1 1 d . . .
H19A H 0.1211 0.5611 0.0682 0.029 Uiso 1 1 calc R . .
H19B H 0.2724 0.5168 0.0226 0.029 Uiso 1 1 calc R . .
H19C H 0.2901 0.6377 0.1127 0.029 Uiso 1 1 calc R . .
C20 C 0.0363(9) 0.4965(6) 0.2795(7) 0.0199(16) Uani 1 1 d . . .
H20A H 0.0425 0.5750 0.3275 0.030 Uiso 1 1 calc R . .
H20B H -0.0210 0.4347 0.3123 0.030 Uiso 1 1 calc R . .
H20C H -0.0230 0.5071 0.1930 0.030 Uiso 1 1 calc R . .
C21 C 0.2758(10) 0.3567(7) 0.5059(6) 0.0213(17) Uani 1 1 d . . .
H21A H 0.2949 0.2687 0.5159 0.032 Uiso 1 1 calc R . .
H21B H 0.1620 0.3735 0.5005 0.032 Uiso 1 1 calc R . .
H21C H 0.3478 0.4044 0.5770 0.032 Uiso 1 1 calc R . .
C22 C 0.6028(8) 0.3096(6) 0.4442(6) 0.0153(15) Uani 1 1 d . . .
H22A H 0.6619 0.3667 0.5128 0.023 Uiso 1 1 calc R . .
H22B H 0.6757 0.2833 0.3959 0.023 Uiso 1 1 calc R . .
H22C H 0.5642 0.2376 0.4768 0.023 Uiso 1 1 calc R . .
C23 C 0.3778(9) 0.0470(7) 0.3093(6) 0.0202(16) Uani 1 1 d . . .
C24 C 0.4738(11) -0.0720(7) 0.3183(8) 0.032(2) Uani 1 1 d . . .
H24A H 0.5178 -0.0822 0.2479 0.048 Uiso 1 1 calc R . .
H24B H 0.4013 -0.1423 0.3176 0.048 Uiso 1 1 calc R . .
H24C H 0.5635 -0.0676 0.3952 0.048 Uiso 1 1 calc R . .
N1 N 0.0327(7) 0.1919(5) 0.1765(5) 0.0109(11) Uani 1 1 d . . .
O1 O 0.3755(5) 0.1056(4) 0.2196(4) 0.0136(10) Uani 1 1 d . . .
O2 O 0.3072(7) 0.0748(5) 0.3896(5) 0.0290(13) Uani 1 1 d . . .
Rh1 Rh 0.26049(5) 0.28108(4) 0.20650(4) 0.0084(3) Uani 1 1 d . . .


_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
C1 N1 1.356(8) . ?
C1 C2 1.377(10) . ?
C1 H1 0.9500 . ?
C2 C3 1.415(9) . ?
C2 H2 0.9500 . ?
C3 C4 1.375(10) . ?
C3 H3 0.9500 . ?
C4 C5 1.408(10) . ?
C4 H4 0.9500 . ?
C5 N1 1.363(8) . ?
C5 C6 1.465(9) . ?
C6 C11 1.402(9) . ?
C6 C7 1.412(9) . ?
C7 C8 1.418(9) . ?
C7 Rh1 2.044(6) . ?
C8 C9 1.404(9) . ?
C8 H8 0.9500 . ?
C9 C10 1.388(9) . ?
C9 H9 0.9500 . ?
C10 C11 1.394(10) . ?
C10 C12 1.519(8) . ?
C11 H11 0.9500 . ?
C12 H12A 0.9800 . ?
C12 H12B 0.9800 . ?
C12 H12C 0.9800 . ?
C13 C14 1.426(9) . ?
C13 C17 1.447(9) . ?
C13 C18 1.505(9) . ?
C13 Rh1 2.176(6) . ?
C14 C15 1.457(9) . ?
C14 C19 1.501(9) . ?
C14 Rh1 2.172(6) . ?
C15 C16 1.445(9) . ?
C15 C20 1.498(10) . ?
C15 Rh1 2.178(6) . ?
C16 C17 1.403(10) . ?
C16 C21 1.507(8) . ?
C16 Rh1 2.274(6) . ?
C17 C22 1.515(9) . ?
C17 Rh1 2.249(6) . ?
C18 H18A 0.9800 . ?
C18 H18B 0.9800 . ?
C18 H18C 0.9800 . ?
C19 H19A 0.9800 . ?
C19 H19B 0.9800 . ?
C19 H19C 0.9800 . ?
C20 H20A 0.9800 . ?
C20 H20B 0.9800 . ?
C20 H20C 0.9800 . ?
C21 H21A 0.9800 . ?
C21 H21B 0.9800 . ?
C21 H21C 0.9800 . ?
C22 H22A 0.9800 . ?
C22 H22B 0.9800 . ?
C22 H22C 0.9800 . ?
C23 O1 1.227(9) . ?
C23 O2 1.259(9) . ?
C23 C24 1.533(11) . ?
C24 H24A 0.9800 . ?
C24 H24B 0.9800 . ?
C24 H24C 0.9800 . ?
N1 Rh1 2.103(6) . ?
O1 Rh1 2.150(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
N1 C1 C2 122.8(6) . . ?
N1 C1 H1 118.6 . . ?
C2 C1 H1 118.6 . . ?
C1 C2 C3 118.4(6) . . ?
C1 C2 H2 120.8 . . ?
C3 C2 H2 120.8 . . ?
C4 C3 C2 118.7(6) . . ?
C4 C3 H3 120.7 . . ?
C2 C3 H3 120.7 . . ?
C3 C4 C5 120.7(6) . . ?
C3 C4 H4 119.7 . . ?
C5 C4 H4 119.7 . . ?
N1 C5 C4 119.8(6) . . ?
N1 C5 C6 113.6(6) . . ?
C4 C5 C6 126.5(6) . . ?
C11 C6 C7 120.6(6) . . ?
C11 C6 C5 123.4(6) . . ?
C7 C6 C5 115.9(5) . . ?
C6 C7 C8 117.8(6) . . ?
C6 C7 Rh1 115.2(4) . . ?
C8 C7 Rh1 127.0(5) . . ?
C9 C8 C7 120.0(6) . . ?
C9 C8 H8 120.0 . . ?
C7 C8 H8 120.0 . . ?
C10 C9 C8 122.0(6) . . ?
C10 C9 H9 119.0 . . ?
C8 C9 H9 119.0 . . ?
C9 C10 C11 118.0(6) . . ?
C9 C10 C12 121.1(6) . . ?
C11 C10 C12 120.9(6) . . ?
C10 C11 C6 121.6(6) . . ?
C10 C11 H11 119.2 . . ?
C6 C11 H11 119.2 . . ?
C10 C12 H12A 109.5 . . ?
C10 C12 H12B 109.5 . . ?
H12A C12 H12B 109.5 . . ?
C10 C12 H12C 109.5 . . ?
H12A C12 H12C 109.5 . . ?
H12B C12 H12C 109.5 . . ?
C14 C13 C17 107.7(6) . . ?
C14 C13 C18 126.0(6) . . ?
C17 C13 C18 125.8(6) . . ?
C14 C13 Rh1 70.7(3) . . ?
C17 C13 Rh1 73.7(4) . . ?
C18 C13 Rh1 127.5(4) . . ?
C13 C14 C15 107.1(5) . . ?
C13 C14 C19 126.8(6) . . ?
C15 C14 C19 125.9(6) . . ?
C13 C14 Rh1 71.0(3) . . ?
C15 C14 Rh1 70.6(3) . . ?
C19 C14 Rh1 127.5(4) . . ?
C16 C15 C14 108.1(6) . . ?
C16 C15 C20 126.0(6) . . ?
C14 C15 C20 125.7(6) . . ?
C16 C15 Rh1 74.7(3) . . ?
C14 C15 Rh1 70.2(3) . . ?
C20 C15 Rh1 124.5(5) . . ?
C17 C16 C15 107.4(5) . . ?
C17 C16 C21 124.8(6) . . ?
C15 C16 C21 127.8(6) . . ?
C17 C16 Rh1 71.0(3) . . ?
C15 C16 Rh1 67.5(3) . . ?
C21 C16 Rh1 128.2(4) . . ?
C16 C17 C13 109.5(6) . . ?
C16 C17 C22 124.6(6) . . ?
C13 C17 C22 125.9(6) . . ?
C16 C17 Rh1 72.9(4) . . ?
C13 C17 Rh1 68.2(3) . . ?
C22 C17 Rh1 125.3(4) . . ?
C13 C18 H18A 109.5 . . ?
C13 C18 H18B 109.5 . . ?
H18A C18 H18B 109.5 . . ?
C13 C18 H18C 109.5 . . ?
H18A C18 H18C 109.5 . . ?
H18B C18 H18C 109.5 . . ?
C14 C19 H19A 109.5 . . ?
C14 C19 H19B 109.5 . . ?
H19A C19 H19B 109.5 . . ?
C14 C19 H19C 109.5 . . ?
H19A C19 H19C 109.5 . . ?
H19B C19 H19C 109.5 . . ?
C15 C20 H20A 109.5 . . ?
C15 C20 H20B 109.5 . . ?
H20A C20 H20B 109.5 . . ?
C15 C20 H20C 109.5 . . ?
H20A C20 H20C 109.5 . . ?
H20B C20 H20C 109.5 . . ?
C16 C21 H21A 109.5 . . ?
C16 C21 H21B 109.5 . . ?
H21A C21 H21B 109.5 . . ?
C16 C21 H21C 109.5 . . ?
H21A C21 H21C 109.5 . . ?
H21B C21 H21C 109.5 . . ?
C17 C22 H22A 109.5 . . ?
C17 C22 H22B 109.5 . . ?
H22A C22 H22B 109.5 . . ?
C17 C22 H22C 109.5 . . ?
H22A C22 H22C 109.5 . . ?
H22B C22 H22C 109.5 . . ?
O1 C23 O2 126.1(7) . . ?
O1 C23 C24 114.7(7) . . ?
O2 C23 C24 119.2(7) . . ?
C23 C24 H24A 109.5 . . ?
C23 C24 H24B 109.5 . . ?
H24A C24 H24B 109.5 . . ?
C23 C24 H24C 109.5 . . ?
H24A C24 H24C 109.5 . . ?
H24B C24 H24C 109.5 . . ?
C1 N1 C5 119.4(6) . . ?
C1 N1 Rh1 124.2(4) . . ?
C5 N1 Rh1 116.3(4) . . ?
C23 O1 Rh1 117.5(4) . . ?
C7 Rh1 N1 78.7(2) . . ?
C7 Rh1 O1 85.5(2) . . ?
N1 Rh1 O1 89.92(18) . . ?
C7 Rh1 C14 96.7(2) . . ?
N1 Rh1 C14 124.4(2) . . ?
O1 Rh1 C14 145.5(2) . . ?
C7 Rh1 C13 106.2(2) . . ?
N1 Rh1 C13 161.6(2) . . ?
O1 Rh1 C13 108.0(2) . . ?
C14 Rh1 C13 38.3(2) . . ?
C7 Rh1 C15 122.5(2) . . ?
N1 Rh1 C15 97.8(2) . . ?
O1 Rh1 C15 151.9(2) . . ?
C14 Rh1 C15 39.1(2) . . ?
C13 Rh1 C15 64.4(2) . . ?
C7 Rh1 C17 142.1(3) . . ?
N1 Rh1 C17 139.2(2) . . ?
O1 Rh1 C17 94.3(2) . . ?
C14 Rh1 C17 63.3(2) . . ?
C13 Rh1 C17 38.1(2) . . ?
C15 Rh1 C17 62.5(2) . . ?
C7 Rh1 C16 159.5(2) . . ?
N1 Rh1 C16 106.3(2) . . ?
O1 Rh1 C16 114.1(2) . . ?
C14 Rh1 C16 63.8(2) . . ?
C13 Rh1 C16 63.0(2) . . ?
C15 Rh1 C16 37.8(2) . . ?
C17 Rh1 C16 36.2(2) . . ?

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
N1 C1 C2 C3 2.6(10) . . . . ?
C1 C2 C3 C4 -0.2(10) . . . . ?
C2 C3 C4 C5 -1.2(10) . . . . ?
C3 C4 C5 N1 0.3(10) . . . . ?
C3 C4 C5 C6 178.9(6) . . . . ?
N1 C5 C6 C11 176.4(6) . . . . ?
C4 C5 C6 C11 -2.3(10) . . . . ?
N1 C5 C6 C7 -3.6(8) . . . . ?
C4 C5 C6 C7 177.7(6) . . . . ?
C11 C6 C7 C8 -1.2(9) . . . . ?
C5 C6 C7 C8 178.8(6) . . . . ?
C11 C6 C7 Rh1 -179.9(5) . . . . ?
C5 C6 C7 Rh1 0.1(7) . . . . ?
C6 C7 C8 C9 1.3(9) . . . . ?
Rh1 C7 C8 C9 179.9(5) . . . . ?
C7 C8 C9 C10 -0.1(10) . . . . ?
C8 C9 C10 C11 -1.3(9) . . . . ?
C8 C9 C10 C12 179.3(6) . . . . ?
C9 C10 C11 C6 1.4(9) . . . . ?
C12 C10 C11 C6 -179.2(6) . . . . ?
C7 C6 C11 C10 -0.2(9) . . . . ?
C5 C6 C11 C10 179.9(6) . . . . ?
C17 C13 C14 C15 -3.1(7) . . . . ?
C18 C13 C14 C15 -175.3(6) . . . . ?
Rh1 C13 C14 C15 61.8(4) . . . . ?
C17 C13 C14 C19 172.0(6) . . . . ?
C18 C13 C14 C19 -0.2(10) . . . . ?
Rh1 C13 C14 C19 -123.2(6) . . . . ?
C17 C13 C14 Rh1 -64.9(4) . . . . ?
C18 C13 C14 Rh1 122.9(6) . . . . ?
C13 C14 C15 C16 3.6(7) . . . . ?
C19 C14 C15 C16 -171.5(6) . . . . ?
Rh1 C14 C15 C16 65.6(4) . . . . ?
C13 C14 C15 C20 179.1(6) . . . . ?
C19 C14 C15 C20 4.0(10) . . . . ?
Rh1 C14 C15 C20 -118.9(6) . . . . ?
C13 C14 C15 Rh1 -62.0(4) . . . . ?
C19 C14 C15 Rh1 122.9(6) . . . . ?
C14 C15 C16 C17 -2.7(7) . . . . ?
C20 C15 C16 C17 -178.2(6) . . . . ?
Rh1 C15 C16 C17 60.0(4) . . . . ?
C14 C15 C16 C21 175.6(6) . . . . ?
C20 C15 C16 C21 0.2(10) . . . . ?
Rh1 C15 C16 C21 -121.6(6) . . . . ?
C14 C15 C16 Rh1 -62.7(4) . . . . ?
C20 C15 C16 Rh1 121.8(6) . . . . ?
C15 C16 C17 C13 0.8(7) . . . . ?
C21 C16 C17 C13 -177.6(6) . . . . ?
Rh1 C16 C17 C13 58.6(4) . . . . ?
C15 C16 C17 C22 -179.2(6) . . . . ?
C21 C16 C17 C22 2.3(10) . . . . ?
Rh1 C16 C17 C22 -121.4(6) . . . . ?
C15 C16 C17 Rh1 -57.8(4) . . . . ?
C21 C16 C17 Rh1 123.8(6) . . . . ?
C14 C13 C17 C16 1.5(7) . . . . ?
C18 C13 C17 C16 173.7(6) . . . . ?
Rh1 C13 C17 C16 -61.5(4) . . . . ?
C14 C13 C17 C22 -178.5(6) . . . . ?
C18 C13 C17 C22 -6.3(10) . . . . ?
Rh1 C13 C17 C22 118.6(6) . . . . ?
C14 C13 C17 Rh1 62.9(4) . . . . ?
C18 C13 C17 Rh1 -124.8(6) . . . . ?
C2 C1 N1 C5 -3.6(9) . . . . ?
C2 C1 N1 Rh1 174.1(5) . . . . ?
C4 C5 N1 C1 2.0(9) . . . . ?
C6 C5 N1 C1 -176.7(5) . . . . ?
C4 C5 N1 Rh1 -175.8(4) . . . . ?
C6 C5 N1 Rh1 5.4(7) . . . . ?
O2 C23 O1 Rh1 6.4(9) . . . . ?
C24 C23 O1 Rh1 -175.2(5) . . . . ?
C6 C7 Rh1 N1 2.1(4) . . . . ?
C8 C7 Rh1 N1 -176.5(6) . . . . ?
C6 C7 Rh1 O1 92.9(5) . . . . ?
C8 C7 Rh1 O1 -85.6(6) . . . . ?
C6 C7 Rh1 C14 -121.7(5) . . . . ?
C8 C7 Rh1 C14 59.8(6) . . . . ?
C6 C7 Rh1 C13 -159.6(4) . . . . ?
C8 C7 Rh1 C13 21.8(6) . . . . ?
C6 C7 Rh1 C15 -90.0(5) . . . . ?
C8 C7 Rh1 C15 91.4(6) . . . . ?
C6 C7 Rh1 C17 -175.8(4) . . . . ?
C8 C7 Rh1 C17 5.6(8) . . . . ?
C6 C7 Rh1 C16 -104.3(8) . . . . ?
C8 C7 Rh1 C16 77.1(10) . . . . ?
C1 N1 Rh1 C7 178.0(5) . . . . ?
C5 N1 Rh1 C7 -4.3(4) . . . . ?
C1 N1 Rh1 O1 92.6(5) . . . . ?
C5 N1 Rh1 O1 -89.7(4) . . . . ?
C1 N1 Rh1 C14 -91.5(5) . . . . ?
C5 N1 Rh1 C14 86.2(5) . . . . ?
C1 N1 Rh1 C13 -74.4(8) . . . . ?
C5 N1 Rh1 C13 103.3(7) . . . . ?
C1 N1 Rh1 C15 -60.2(5) . . . . ?
C5 N1 Rh1 C15 117.5(4) . . . . ?
C1 N1 Rh1 C17 -3.9(7) . . . . ?
C5 N1 Rh1 C17 173.8(4) . . . . ?
C1 N1 Rh1 C16 -22.5(5) . . . . ?
C5 N1 Rh1 C16 155.2(4) . . . . ?
C23 O1 Rh1 C7 -147.0(5) . . . . ?
C23 O1 Rh1 N1 -68.3(5) . . . . ?
C23 O1 Rh1 C14 117.7(5) . . . . ?
C23 O1 Rh1 C13 107.4(5) . . . . ?
C23 O1 Rh1 C15 38.3(7) . . . . ?
C23 O1 Rh1 C17 71.0(5) . . . . ?
C23 O1 Rh1 C16 39.6(5) . . . . ?
C13 C14 Rh1 C7 -107.7(4) . . . . ?
C15 C14 Rh1 C7 135.5(4) . . . . ?
C19 C14 Rh1 C7 14.6(6) . . . . ?
C13 C14 Rh1 N1 171.4(3) . . . . ?
C15 C14 Rh1 N1 54.6(4) . . . . ?
C19 C14 Rh1 N1 -66.3(7) . . . . ?
C13 C14 Rh1 O1 -15.9(5) . . . . ?
C15 C14 Rh1 O1 -132.7(4) . . . . ?
C19 C14 Rh1 O1 106.4(6) . . . . ?
C15 C14 Rh1 C13 -116.8(5) . . . . ?
C19 C14 Rh1 C13 122.3(7) . . . . ?
C13 C14 Rh1 C15 116.8(5) . . . . ?
C19 C14 Rh1 C15 -120.9(8) . . . . ?
C13 C14 Rh1 C17 38.4(4) . . . . ?
C15 C14 Rh1 C17 -78.4(4) . . . . ?
C19 C14 Rh1 C17 160.7(7) . . . . ?
C13 C14 Rh1 C16 79.0(4) . . . . ?
C15 C14 Rh1 C16 -37.8(4) . . . . ?
C19 C14 Rh1 C16 -158.7(7) . . . . ?
C14 C13 Rh1 C7 80.1(4) . . . . ?
C17 C13 Rh1 C7 -163.9(4) . . . . ?
C18 C13 Rh1 C7 -41.0(6) . . . . ?
C14 C13 Rh1 N1 -23.1(8) . . . . ?
C17 C13 Rh1 N1 93.0(7) . . . . ?
C18 C13 Rh1 N1 -144.1(6) . . . . ?
C14 C13 Rh1 O1 170.6(3) . . . . ?
C17 C13 Rh1 O1 -73.4(4) . . . . ?
C18 C13 Rh1 O1 49.5(6) . . . . ?
C17 C13 Rh1 C14 116.0(5) . . . . ?
C18 C13 Rh1 C14 -121.1(7) . . . . ?
C14 C13 Rh1 C15 -38.7(4) . . . . ?
C17 C13 Rh1 C15 77.4(4) . . . . ?
C18 C13 Rh1 C15 -159.7(6) . . . . ?
C14 C13 Rh1 C17 -116.0(5) . . . . ?
C18 C13 Rh1 C17 122.9(7) . . . . ?
C14 C13 Rh1 C16 -81.0(4) . . . . ?
C17 C13 Rh1 C16 35.0(4) . . . . ?
C18 C13 Rh1 C16 157.9(6) . . . . ?
C16 C15 Rh1 C7 -171.9(4) . . . . ?
C14 C15 Rh1 C7 -55.7(5) . . . . ?
C20 C15 Rh1 C7 64.7(6) . . . . ?
C16 C15 Rh1 N1 106.6(4) . . . . ?
C14 C15 Rh1 N1 -137.2(4) . . . . ?
C20 C15 Rh1 N1 -16.9(6) . . . . ?
C16 C15 Rh1 O1 1.9(7) . . . . ?
C14 C15 Rh1 O1 118.1(5) . . . . ?
C20 C15 Rh1 O1 -121.6(6) . . . . ?
C16 C15 Rh1 C14 -116.2(6) . . . . ?
C20 C15 Rh1 C14 120.4(7) . . . . ?
C16 C15 Rh1 C13 -78.3(4) . . . . ?
C14 C15 Rh1 C13 37.8(4) . . . . ?
C20 C15 Rh1 C13 158.2(6) . . . . ?
C16 C15 Rh1 C17 -35.6(4) . . . . ?
C14 C15 Rh1 C17 80.6(4) . . . . ?
C20 C15 Rh1 C17 -159.0(6) . . . . ?
C14 C15 Rh1 C16 116.2(6) . . . . ?
C20 C15 Rh1 C16 -123.5(7) . . . . ?
C16 C17 Rh1 C7 145.7(4) . . . . ?
C13 C17 Rh1 C7 25.8(6) . . . . ?
C22 C17 Rh1 C7 -93.6(7) . . . . ?
C16 C17 Rh1 N1 -31.2(5) . . . . ?
C13 C17 Rh1 N1 -151.1(4) . . . . ?
C22 C17 Rh1 N1 89.5(6) . . . . ?
C16 C17 Rh1 O1 -126.1(4) . . . . ?
C13 C17 Rh1 O1 114.0(4) . . . . ?
C22 C17 Rh1 O1 -5.4(6) . . . . ?
C16 C17 Rh1 C14 81.4(4) . . . . ?
C13 C17 Rh1 C14 -38.6(4) . . . . ?
C22 C17 Rh1 C14 -157.9(7) . . . . ?
C16 C17 Rh1 C13 119.9(5) . . . . ?
C22 C17 Rh1 C13 -119.4(7) . . . . ?
C16 C17 Rh1 C15 37.2(4) . . . . ?
C13 C17 Rh1 C15 -82.8(4) . . . . ?
C22 C17 Rh1 C15 157.9(7) . . . . ?
C13 C17 Rh1 C16 -119.9(5) . . . . ?
C22 C17 Rh1 C16 120.7(7) . . . . ?
C17 C16 Rh1 C7 -99.2(8) . . . . ?
C15 C16 Rh1 C7 19.9(9) . . . . ?
C21 C16 Rh1 C7 141.1(7) . . . . ?
C17 C16 Rh1 N1 159.3(4) . . . . ?
C15 C16 Rh1 N1 -81.6(4) . . . . ?
C21 C16 Rh1 N1 39.6(7) . . . . ?
C17 C16 Rh1 O1 61.9(4) . . . . ?
C15 C16 Rh1 O1 -179.0(4) . . . . ?
C21 C16 Rh1 O1 -57.8(7) . . . . ?
C17 C16 Rh1 C14 -79.9(4) . . . . ?
C15 C16 Rh1 C14 39.2(4) . . . . ?
C21 C16 Rh1 C14 160.4(7) . . . . ?
C17 C16 Rh1 C13 -36.9(4) . . . . ?
C15 C16 Rh1 C13 82.2(4) . . . . ?
C21 C16 Rh1 C13 -156.6(7) . . . . ?
C17 C16 Rh1 C15 -119.1(6) . . . . ?
C21 C16 Rh1 C15 121.2(8) . . . . ?
C15 C16 Rh1 C17 119.1(6) . . . . ?
C21 C16 Rh1 C17 -119.7(8) . . . . ?

_diffrn_measured_fraction_theta_max 0.917
_diffrn_reflns_theta_full        25.00
_diffrn_measured_fraction_theta_full 0.917
_refine_diff_density_max         1.193
_refine_diff_density_min         -1.693
_refine_diff_density_rms         0.395
####################################################################### 
# 
# 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_1_CCDC2
_database_code_depnum_ccdc_archive 'CCDC 1563729'
_audit_update_record             
;
2017-07-21 deposited with the CCDC.
2017-10-13 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C2.44 H1.78 N0.22 O0.22'
_chemical_formula_weight         37.82

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'

_symmetry_cell_setting           Triclinic
_symmetry_space_group_name_H-M   P-1

loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   7.1832(10)
_cell_length_b                   10.3531(16)
_cell_length_c                   12.7041(18)
_cell_angle_alpha                99.499(6)
_cell_angle_beta                 102.356(6)
_cell_angle_gamma                98.881(5)
_cell_volume                     892.4(2)
_cell_formula_units_Z            18
_cell_measurement_temperature    150(2)
_cell_measurement_reflns_used    8216
_cell_measurement_theta_min      2.89
_cell_measurement_theta_max      26.39

_exptl_crystal_description       Block
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.20
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.20
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.267
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             356
_exptl_absorpt_coefficient_mu    0.082
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.9837
_exptl_absorpt_correction_T_max  0.9837
_exptl_absorpt_process_details   sadabs

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      150(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            15137
_diffrn_reflns_av_R_equivalents  0.0323
_diffrn_reflns_av_sigmaI/netI    0.0259
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_theta_min         2.89
_diffrn_reflns_theta_max         26.43
_reflns_number_total             3627
_reflns_number_gt                3199
_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)+(0.0420P)²+0.3300P] 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         3627
_refine_ls_number_parameters     236
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0429
_refine_ls_R_factor_gt           0.0369
_refine_ls_wR_factor_ref         0.0987
_refine_ls_wR_factor_gt          0.0949
_refine_ls_goodness_of_fit_ref   1.052
_refine_ls_restrained_S_all      1.052
_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
O1 O 0.11599(12) 0.29982(8) 0.76006(7) 0.0218(2) Uani 1 1 d . . .
O2 O 0.12901(12) 0.15938(8) 0.60705(7) 0.0244(2) Uani 1 1 d . . .
C1 C -0.96154(18) -0.32219(12) 0.58075(10) 0.0231(3) Uani 1 1 d . . .
N1 N -1.10756(16) -0.38902(11) 0.57545(10) 0.0304(3) Uani 1 1 d . . .
C2 C -0.73402(17) -0.10764(12) 0.65064(10) 0.0215(3) Uani 1 1 d . . .
H2 H -0.8252 -0.0751 0.6870 0.026 Uiso 1 1 calc R . .
C3 C -0.46992(17) -0.20337(12) 0.54187(10) 0.0219(3) Uani 1 1 d . . .
H3 H -0.3801 -0.2353 0.5041 0.026 Uiso 1 1 calc R . .
C4 C 0.44783(18) 0.32743(12) 0.86098(10) 0.0215(3) Uani 1 1 d . . .
C5 C -0.55785(17) -0.02620(12) 0.65867(10) 0.0205(2) Uani 1 1 d . . .
H5 H -0.5283 0.0625 0.7007 0.025 Uiso 1 1 calc R . .
C6 C -0.42260(16) -0.07333(11) 0.60533(9) 0.0187(2) Uani 1 1 d . . .
C7 C 0.31342(17) 0.35555(11) 0.77551(10) 0.0205(3) Uani 1 1 d . . .
C8 C -0.77736(17) -0.23792(12) 0.58876(10) 0.0199(2) Uani 1 1 d . . .
C9 C 0.64103(18) 0.39342(13) 0.88098(10) 0.0251(3) Uani 1 1 d . . .
H9 H 0.7350 0.3771 0.9397 0.030 Uiso 1 1 calc R . .
C10 C -0.23326(17) 0.00885(12) 0.61162(10) 0.0194(2) Uani 1 1 d . . .
H10 H -0.1608 -0.0255 0.5629 0.023 Uiso 1 1 calc R . .
N2 N 0.27291(16) 0.11580(11) 0.87859(9) 0.0282(3) Uani 1 1 d . . .
C11 C -0.64558(18) -0.28596(12) 0.53339(10) 0.0228(3) Uani 1 1 d . . .
H11 H -0.6762 -0.3742 0.4905 0.027 Uiso 1 1 calc R . .
C12 C 0.36797(18) 0.44196(12) 0.71037(10) 0.0242(3) Uani 1 1 d . . .
H12 H 0.2737 0.4587 0.6520 0.029 Uiso 1 1 calc R . .
C13 C 0.04204(17) 0.19256(11) 0.67461(9) 0.0191(2) Uani 1 1 d . . .
C14 C -0.15236(17) 0.12666(12) 0.67848(10) 0.0210(3) Uani 1 1 d . . .
H14 H -0.2190 0.1674 0.7278 0.025 Uiso 1 1 calc R . .
C15 C 0.70044(19) 0.48212(13) 0.81791(11) 0.0264(3) Uani 1 1 d . . .
C16 C 0.56188(19) 0.50420(13) 0.73108(10) 0.0263(3) Uani 1 1 d . . .
H16 H 0.6002 0.5623 0.6856 0.032 Uiso 1 1 calc R . .
C17 C 0.9088(2) 0.55610(15) 0.84562(13) 0.0372(3) Uani 1 1 d . . .
H17A H 0.9222 0.6427 0.8943 0.056 Uiso 1 1 calc R . .
H17B H 0.9454 0.5702 0.7777 0.056 Uiso 1 1 calc R . .
H17C H 0.9941 0.5034 0.8827 0.056 Uiso 1 1 calc R . .
C18 C 0.4656(2) 0.26545(14) 1.04440(11) 0.0295(3) Uani 1 1 d . . .
H18 H 0.5502 0.3487 1.0786 0.035 Uiso 1 1 calc R . .
C19 C 0.2267(2) 0.03001(14) 0.94126(13) 0.0353(3) Uani 1 1 d . . .
H19 H 0.1436 -0.0533 0.9056 0.042 Uiso 1 1 calc R . .
C20 C 0.39271(18) 0.23278(12) 0.93060(10) 0.0229(3) Uani 1 1 d . . .
C21 C 0.4133(2) 0.17509(15) 1.10695(12) 0.0378(3) Uani 1 1 d . . .
H21 H 0.4602 0.1957 1.1848 0.045 Uiso 1 1 calc R . .
C22 C 0.2920(2) 0.05468(15) 1.05466(13) 0.0389(4) Uani 1 1 d . . .
H22 H 0.2543 -0.0097 1.0954 0.047 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
O1 C13 1.3664(14) . ?
O1 C7 1.4048(14) . ?
O2 C13 1.2014(15) . ?
C1 N1 1.1462(16) . ?
C1 C8 1.4417(16) . ?
C2 C5 1.3818(16) . ?
C2 C8 1.3964(17) . ?
C3 C11 1.3832(17) . ?
C3 C6 1.4004(17) . ?
C4 C7 1.3923(17) . ?
C4 C9 1.3987(17) . ?
C4 C20 1.4885(17) . ?
C5 C6 1.4001(16) . ?
C6 C10 1.4675(16) . ?
C7 C12 1.3833(17) . ?
C8 C11 1.3975(17) . ?
C9 C15 1.3913(19) . ?
C10 C14 1.3322(17) . ?
N2 C19 1.3373(18) . ?
N2 C20 1.3471(16) . ?
C12 C16 1.3909(18) . ?
C13 C14 1.4711(16) . ?
C15 C16 1.3941(19) . ?
C15 C17 1.5109(18) . ?
C18 C21 1.383(2) . ?
C18 C20 1.3923(18) . ?
C19 C22 1.383(2) . ?
C21 C22 1.378(2) . ?

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
C13 O1 C7 115.47(9) . . ?
N1 C1 C8 179.35(13) . . ?
C5 C2 C8 119.69(11) . . ?
C11 C3 C6 120.96(11) . . ?
C7 C4 C9 117.27(11) . . ?
C7 C4 C20 122.69(11) . . ?
C9 C4 C20 120.04(11) . . ?
C2 C5 C6 120.52(11) . . ?
C5 C6 C3 119.05(11) . . ?
C5 C6 C10 122.66(11) . . ?
C3 C6 C10 118.28(11) . . ?
C12 C7 C4 121.86(11) . . ?
C12 C7 O1 119.71(11) . . ?
C4 C7 O1 118.32(11) . . ?
C2 C8 C11 120.61(11) . . ?
C2 C8 C1 119.33(11) . . ?
C11 C8 C1 120.05(11) . . ?
C15 C9 C4 122.34(12) . . ?
C14 C10 C6 126.80(11) . . ?
C19 N2 C20 116.97(12) . . ?
C3 C11 C8 119.15(11) . . ?
C7 C12 C16 119.48(12) . . ?
O2 C13 O1 122.79(10) . . ?
O2 C13 C14 126.26(11) . . ?
O1 C13 C14 110.95(10) . . ?
C10 C14 C13 118.81(11) . . ?
C9 C15 C16 118.40(12) . . ?
C9 C15 C17 120.60(12) . . ?
C16 C15 C17 120.97(12) . . ?
C12 C16 C15 120.61(12) . . ?
C21 C18 C20 119.11(13) . . ?
N2 C19 C22 124.28(14) . . ?
N2 C20 C18 122.46(12) . . ?
N2 C20 C4 117.17(11) . . ?
C18 C20 C4 120.36(11) . . ?
C22 C21 C18 118.99(13) . . ?
C21 C22 C19 118.18(13) . . ?

_diffrn_measured_fraction_theta_max 0.992
_diffrn_reflns_theta_full        26.43
_diffrn_measured_fraction_theta_full 0.992
_refine_diff_density_max         0.234
_refine_diff_density_min         -0.187
_refine_diff_density_rms         0.038
