# Electronic Supplementary Material (ESI) for Organic & Biomolecular Chemistry.
# This journal is © The Royal Society of Chemistry 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_azac6h4omerhco
_database_code_depnum_ccdc_archive 'CCDC 1515290'
_audit_update_record             
;
2016-11-07 deposited with the CCDC.
2017-01-25 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C17 H14 Cl N2 O3 Rh'
_chemical_formula_sum            'C17 H14 Cl N2 O3 Rh'
_chemical_formula_weight         432.66

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'
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'

_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_H-M   'P 21/n       '
_symmetry_Int_Tables_number      14

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                   11.611(3)
_cell_length_b                   7.436(2)
_cell_length_c                   20.143(6)
_cell_angle_alpha                90.00
_cell_angle_beta                 95.124(4)
_cell_angle_gamma                90.00
_cell_volume                     1732.3(8)
_cell_formula_units_Z            4
_cell_measurement_temperature    193(2)
_cell_measurement_reflns_used    5473
_cell_measurement_theta_min      1.8
_cell_measurement_theta_max      30.7

_exptl_crystal_description       Block
_exptl_crystal_colour            Yellow
_exptl_crystal_size_max          0.42
_exptl_crystal_size_mid          0.28
_exptl_crystal_size_min          0.14
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.659
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             864
_exptl_absorpt_coefficient_mu    1.157
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(Jacobson, 1998)'
_exptl_absorpt_correction_T_min  0.512
_exptl_absorpt_correction_T_max  0.851

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      193(2)
_diffrn_radiation_wavelength     0.71075
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Rigaku/MSC Mercury CCD'
_diffrn_measurement_method       ω
_diffrn_detector_area_resol_mean 14.63
_diffrn_reflns_number            12913
_diffrn_reflns_av_R_equivalents  0.0376
_diffrn_reflns_av_sigmaI/netI    0.0400
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_k_min       -6
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_l_min       -26
_diffrn_reflns_limit_l_max       26
_diffrn_reflns_theta_min         1.95
_diffrn_reflns_theta_max         27.50
_reflns_number_total             3927
_reflns_number_gt                3194
_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)+(0.0707P)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    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         3927
_refine_ls_number_parameters     219
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0459
_refine_ls_R_factor_gt           0.0368
_refine_ls_wR_factor_ref         0.1267
_refine_ls_wR_factor_gt          0.1014
_refine_ls_goodness_of_fit_ref   1.113
_refine_ls_restrained_S_all      1.113
_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
Cl1 Cl 0.19534(9) -0.23354(14) 0.47826(5) 0.0613(3) Uani 1 1 d . . .
Rh1 Rh 0.28163(2) 0.04911(4) 0.466907(13) 0.04229(13) Uani 1 1 d . . .
O1 O 0.4020(3) 0.3971(5) 0.45309(19) 0.0864(10) Uani 1 1 d . . .
O2 O 0.3786(3) -0.0177(6) 0.60939(18) 0.0895(11) Uani 1 1 d . . .
O3 O -0.36413(18) 0.1755(4) 0.13624(12) 0.0501(6) Uani 1 1 d . . .
N1 N 0.2585(2) 0.0873(3) 0.31375(14) 0.0348(6) Uani 1 1 d . . .
N2 N 0.0907(2) 0.0885(4) 0.34932(13) 0.0358(6) Uani 1 1 d . . .
C1 C 0.3541(3) 0.2658(6) 0.4585(2) 0.0578(10) Uani 1 1 d . . .
C2 C 0.3454(4) 0.0126(6) 0.5565(2) 0.0604(10) Uani 1 1 d . . .
C3 C 0.2046(3) 0.0773(4) 0.37093(17) 0.0366(7) Uani 1 1 d . . .
C4 C 0.0714(2) 0.1067(4) 0.28071(16) 0.0341(6) Uani 1 1 d . . .
C5 C 0.1797(2) 0.1059(4) 0.25752(16) 0.0334(6) Uani 1 1 d . . .
C6 C 0.2231(3) 0.1252(4) 0.19416(17) 0.0409(7) Uani 1 1 d . . .
H6 H 0.1719 0.1404 0.1551 0.049 Uiso 1 1 calc R . .
C7 C 0.3395(3) 0.1215(5) 0.1906(2) 0.0490(9) Uani 1 1 d . . .
H7 H 0.3695 0.1348 0.1485 0.059 Uiso 1 1 calc R . .
C8 C 0.4170(3) 0.0980(5) 0.2486(2) 0.0480(9) Uani 1 1 d . . .
H8 H 0.4980 0.0951 0.2448 0.058 Uiso 1 1 calc R . .
C9 C 0.3771(3) 0.0802(4) 0.3081(2) 0.0431(8) Uani 1 1 d . . .
H9 H 0.4294 0.0627 0.3466 0.052 Uiso 1 1 calc R . .
C10 C 0.0002(3) 0.0765(5) 0.39625(18) 0.0468(8) Uani 1 1 d . . .
H10 H 0.0283 0.0028 0.4347 0.070 Uiso 1 1 calc R . .
H10A H -0.0693 0.0213 0.3738 0.070 Uiso 1 1 calc R . .
H10B H -0.0184 0.1974 0.4114 0.070 Uiso 1 1 calc R . .
C11 C -0.0419(2) 0.1224(4) 0.24257(16) 0.0329(6) Uani 1 1 d . . .
C12 C -0.1293(2) 0.2337(4) 0.26344(17) 0.0378(7) Uani 1 1 d . . .
H12 H -0.1157 0.3004 0.3036 0.045 Uiso 1 1 calc R . .
C13 C -0.2343(3) 0.2475(5) 0.22650(17) 0.0413(7) Uani 1 1 d . . .
H13 H -0.2928 0.3225 0.2416 0.050 Uiso 1 1 calc R . .
C14 C -0.2556(2) 0.1533(4) 0.16755(16) 0.0360(6) Uani 1 1 d . . .
C15 C -0.1698(3) 0.0455(4) 0.14494(17) 0.0359(7) Uani 1 1 d . . .
H15 H -0.1830 -0.0175 0.1039 0.043 Uiso 1 1 calc R . .
C16 C -0.0651(3) 0.0307(4) 0.18281(17) 0.0344(7) Uani 1 1 d . . .
H16 H -0.0069 -0.0446 0.1675 0.041 Uiso 1 1 calc R . .
C17 C -0.3890(3) 0.0973(6) 0.0725(2) 0.0517(9) Uani 1 1 d . . .
H17 H -0.3365 0.1467 0.0416 0.077 Uiso 1 1 calc R . .
H17A H -0.4691 0.1243 0.0560 0.077 Uiso 1 1 calc R . .
H17B H -0.3786 -0.0333 0.0757 0.077 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
Cl1 Rh1 2.3484(11) . ?
Rh1 C1 1.833(4) . ?
Rh1 C2 1.907(5) . ?
Rh1 C3 2.067(4) . ?
O1 C1 1.134(5) . ?
O2 C2 1.124(6) . ?
O3 C14 1.368(4) . ?
O3 C17 1.416(4) . ?
N1 C3 1.361(4) . ?
N1 C9 1.393(4) . ?
N1 C5 1.398(4) . ?
N2 C3 1.357(4) . ?
N2 C4 1.387(4) . ?
N2 C10 1.478(4) . ?
C4 C5 1.379(4) . ?
C4 C11 1.468(4) . ?
C5 C6 1.421(4) . ?
C6 C7 1.359(5) . ?
C6 H6 0.9500 . ?
C7 C8 1.420(6) . ?
C7 H7 0.9500 . ?
C8 C9 1.329(5) . ?
C8 H8 0.9500 . ?
C9 H9 0.9500 . ?
C10 H10 0.9800 . ?
C10 H10A 0.9800 . ?
C10 H10B 0.9800 . ?
C11 C16 1.389(4) . ?
C11 C12 1.402(4) . ?
C12 C13 1.375(4) . ?
C12 H12 0.9500 . ?
C13 C14 1.382(4) . ?
C13 H13 0.9500 . ?
C14 C15 1.387(4) . ?
C15 C16 1.381(5) . ?
C15 H15 0.9500 . ?
C16 H16 0.9500 . ?
C17 H17 0.9800 . ?
C17 H17A 0.9800 . ?
C17 H17B 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
C1 Rh1 C2 94.0(2) . . ?
C1 Rh1 C3 89.36(16) . . ?
C2 Rh1 C3 176.43(16) . . ?
C1 Rh1 Cl1 177.91(13) . . ?
C2 Rh1 Cl1 85.03(15) . . ?
C3 Rh1 Cl1 91.66(9) . . ?
C14 O3 C17 118.3(2) . . ?
C3 N1 C9 126.9(3) . . ?
C3 N1 C5 111.9(3) . . ?
C9 N1 C5 121.2(3) . . ?
C3 N2 C4 113.0(2) . . ?
C3 N2 C10 121.3(3) . . ?
C4 N2 C10 125.6(3) . . ?
O1 C1 Rh1 177.9(4) . . ?
O2 C2 Rh1 175.8(5) . . ?
N2 C3 N1 103.5(3) . . ?
N2 C3 Rh1 129.3(2) . . ?
N1 C3 Rh1 127.1(2) . . ?
C5 C4 N2 105.4(3) . . ?
C5 C4 C11 128.6(3) . . ?
N2 C4 C11 125.9(2) . . ?
C4 C5 N1 106.1(3) . . ?
C4 C5 C6 135.3(3) . . ?
N1 C5 C6 118.6(3) . . ?
C7 C6 C5 118.7(3) . . ?
C7 C6 H6 120.7 . . ?
C5 C6 H6 120.7 . . ?
C6 C7 C8 121.2(3) . . ?
C6 C7 H7 119.4 . . ?
C8 C7 H7 119.4 . . ?
C9 C8 C7 120.5(3) . . ?
C9 C8 H8 119.7 . . ?
C7 C8 H8 119.7 . . ?
C8 C9 N1 119.8(3) . . ?
C8 C9 H9 120.1 . . ?
N1 C9 H9 120.1 . . ?
N2 C10 H10 109.5 . . ?
N2 C10 H10A 109.5 . . ?
H10 C10 H10A 109.5 . . ?
N2 C10 H10B 109.5 . . ?
H10 C10 H10B 109.5 . . ?
H10A C10 H10B 109.5 . . ?
C16 C11 C12 117.4(3) . . ?
C16 C11 C4 120.6(2) . . ?
C12 C11 C4 121.9(3) . . ?
C13 C12 C11 120.8(3) . . ?
C13 C12 H12 119.6 . . ?
C11 C12 H12 119.6 . . ?
C12 C13 C14 120.6(3) . . ?
C12 C13 H13 119.7 . . ?
C14 C13 H13 119.7 . . ?
O3 C14 C13 114.9(3) . . ?
O3 C14 C15 125.3(3) . . ?
C13 C14 C15 119.8(3) . . ?
C16 C15 C14 119.2(3) . . ?
C16 C15 H15 120.4 . . ?
C14 C15 H15 120.4 . . ?
C15 C16 C11 122.2(3) . . ?
C15 C16 H16 118.9 . . ?
C11 C16 H16 118.9 . . ?
O3 C17 H17 109.5 . . ?
O3 C17 H17A 109.5 . . ?
H17 C17 H17A 109.5 . . ?
O3 C17 H17B 109.5 . . ?
H17 C17 H17B 109.5 . . ?
H17A C17 H17B 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
C2 Rh1 C1 O1 78(12) . . . . ?
C3 Rh1 C1 O1 -103(12) . . . . ?
Cl1 Rh1 C1 O1 16(15) . . . . ?
C1 Rh1 C2 O2 172(5) . . . . ?
C3 Rh1 C2 O2 12(7) . . . . ?
Cl1 Rh1 C2 O2 -10(5) . . . . ?
C4 N2 C3 N1 -0.5(3) . . . . ?
C10 N2 C3 N1 177.9(3) . . . . ?
C4 N2 C3 Rh1 -180.0(2) . . . . ?
C10 N2 C3 Rh1 -1.6(4) . . . . ?
C9 N1 C3 N2 -179.3(3) . . . . ?
C5 N1 C3 N2 0.5(3) . . . . ?
C9 N1 C3 Rh1 0.2(4) . . . . ?
C5 N1 C3 Rh1 179.9(2) . . . . ?
C1 Rh1 C3 N2 -118.3(3) . . . . ?
C2 Rh1 C3 N2 42(2) . . . . ?
Cl1 Rh1 C3 N2 63.6(3) . . . . ?
C1 Rh1 C3 N1 62.4(3) . . . . ?
C2 Rh1 C3 N1 -138(2) . . . . ?
Cl1 Rh1 C3 N1 -115.8(3) . . . . ?
C3 N2 C4 C5 0.3(4) . . . . ?
C10 N2 C4 C5 -178.0(3) . . . . ?
C3 N2 C4 C11 -179.9(3) . . . . ?
C10 N2 C4 C11 1.8(5) . . . . ?
N2 C4 C5 N1 0.0(3) . . . . ?
C11 C4 C5 N1 -179.8(3) . . . . ?
N2 C4 C5 C6 -177.4(4) . . . . ?
C11 C4 C5 C6 2.8(6) . . . . ?
C3 N1 C5 C4 -0.3(3) . . . . ?
C9 N1 C5 C4 179.5(3) . . . . ?
C3 N1 C5 C6 177.6(3) . . . . ?
C9 N1 C5 C6 -2.6(4) . . . . ?
C4 C5 C6 C7 178.3(3) . . . . ?
N1 C5 C6 C7 1.2(5) . . . . ?
C5 C6 C7 C8 0.3(5) . . . . ?
C6 C7 C8 C9 -0.4(6) . . . . ?
C7 C8 C9 N1 -1.0(5) . . . . ?
C3 N1 C9 C8 -177.7(3) . . . . ?
C5 N1 C9 C8 2.5(5) . . . . ?
C5 C4 C11 C16 41.7(5) . . . . ?
N2 C4 C11 C16 -138.1(3) . . . . ?
C5 C4 C11 C12 -136.3(3) . . . . ?
N2 C4 C11 C12 44.0(5) . . . . ?
C16 C11 C12 C13 1.4(5) . . . . ?
C4 C11 C12 C13 179.3(3) . . . . ?
C11 C12 C13 C14 -0.7(5) . . . . ?
C17 O3 C14 C13 174.1(3) . . . . ?
C17 O3 C14 C15 -6.5(5) . . . . ?
C12 C13 C14 O3 178.7(3) . . . . ?
C12 C13 C14 C15 -0.8(5) . . . . ?
O3 C14 C15 C16 -177.8(3) . . . . ?
C13 C14 C15 C16 1.5(5) . . . . ?
C14 C15 C16 C11 -0.9(5) . . . . ?
C12 C11 C16 C15 -0.6(4) . . . . ?
C4 C11 C16 C15 -178.6(3) . . . . ?

_diffrn_measured_fraction_theta_max 0.988
_diffrn_reflns_theta_full        27.50
_diffrn_measured_fraction_theta_full 0.988
_refine_diff_density_max         1.056
_refine_diff_density_min         -1.100
_refine_diff_density_rms         0.163
####################################################################### 
# 
# 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_aprc
_database_code_depnum_ccdc_archive 'CCDC 1515285'
_audit_update_record             
;
2016-11-07 deposited with the CCDC.
2017-01-25 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C16 H12 Cl N2 O2 Rh'
_chemical_formula_sum            'C16 H12 Cl N2 O2 Rh'
_chemical_formula_weight         402.64

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'
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'

_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_H-M   'P 21/a       '
_symmetry_Int_Tables_number      14

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

_cell_length_a                   7.875(2)
_cell_length_b                   16.458(4)
_cell_length_c                   12.568(3)
_cell_angle_alpha                90.00
_cell_angle_beta                 100.553(3)
_cell_angle_gamma                90.00
_cell_volume                     1601.3(7)
_cell_formula_units_Z            4
_cell_measurement_temperature    193(2)
_cell_measurement_reflns_used    4182
_cell_measurement_theta_min      1.6
_cell_measurement_theta_max      31.0

_exptl_crystal_description       Block
_exptl_crystal_colour            Yellow
_exptl_crystal_size_max          0.37
_exptl_crystal_size_mid          0.14
_exptl_crystal_size_min          0.02
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.670
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             800
_exptl_absorpt_coefficient_mu    1.240
_exptl_absorpt_correction_type   integration
_exptl_absorpt_process_details   '(Higashi, 1999)'
_exptl_absorpt_correction_T_min  0.741
_exptl_absorpt_correction_T_max  0.968

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      193(2)
_diffrn_radiation_wavelength     0.71075
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Rigaku/MSC Mercury CCD'
_diffrn_measurement_method       ω
_diffrn_detector_area_resol_mean 14.63
_diffrn_reflns_number            13157
_diffrn_reflns_av_R_equivalents  0.0456
_diffrn_reflns_av_sigmaI/netI    0.0475
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -21
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_theta_min         1.65
_diffrn_reflns_theta_max         27.50
_reflns_number_total             3679
_reflns_number_gt                2971
_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)+(0.0315P)²+0.9212P] 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         3679
_refine_ls_number_parameters     200
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0579
_refine_ls_R_factor_gt           0.0420
_refine_ls_wR_factor_ref         0.0896
_refine_ls_wR_factor_gt          0.0827
_refine_ls_goodness_of_fit_ref   1.089
_refine_ls_restrained_S_all      1.089
_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 0.99157(4) 0.459159(15) 0.28535(2) 0.03446(10) Uani 1 1 d . . .
Cl1 Cl 0.72555(13) 0.50417(6) 0.32151(9) 0.0494(3) Uani 1 1 d . . .
O1 O 0.8822(4) 0.28395(14) 0.3031(3) 0.0595(9) Uani 1 1 d . . .
O2 O 1.3335(5) 0.4083(2) 0.2429(4) 0.0999(15) Uani 1 1 d . . .
N1 N 1.1446(4) 0.63158(16) 0.3314(2) 0.0311(6) Uani 1 1 d . . .
N2 N 0.9893(4) 0.62451(15) 0.1730(2) 0.0313(6) Uani 1 1 d . . .
C1 C 0.9232(5) 0.3494(2) 0.2996(3) 0.0416(9) Uani 1 1 d . . .
C2 C 1.2021(6) 0.4278(2) 0.2575(4) 0.0598(13) Uani 1 1 d . . .
C3 C 1.0512(5) 0.57904(19) 0.2610(3) 0.0321(8) Uani 1 1 d . . .
C4 C 1.0406(4) 0.70558(18) 0.1869(3) 0.0289(7) Uani 1 1 d . . .
C5 C 1.1388(4) 0.71070(18) 0.2877(3) 0.0297(7) Uani 1 1 d . . .
C6 C 1.2318(5) 0.7733(2) 0.3509(3) 0.0366(8) Uani 1 1 d . . .
H6 H 1.2300 0.8272 0.3238 0.044 Uiso 1 1 calc R . .
C7 C 1.3221(5) 0.7556(2) 0.4495(3) 0.0454(10) Uani 1 1 d . . .
H7 H 1.3851 0.7973 0.4917 0.054 Uiso 1 1 calc R . .
C8 C 1.3251(6) 0.6751(2) 0.4917(3) 0.0509(11) Uani 1 1 d . . .
H8 H 1.3897 0.6641 0.5618 0.061 Uiso 1 1 calc R . .
C9 C 1.2381(5) 0.6146(2) 0.4341(3) 0.0408(9) Uani 1 1 d . . .
H9 H 1.2403 0.5612 0.4629 0.049 Uiso 1 1 calc R . .
C10 C 0.8754(5) 0.59112(19) 0.0784(3) 0.0384(9) Uani 1 1 d . . .
H10 H 0.9447 0.5722 0.0260 0.058 Uiso 1 1 calc R . .
H10A H 0.7951 0.6333 0.0451 0.058 Uiso 1 1 calc R . .
H10B H 0.8100 0.5455 0.1006 0.058 Uiso 1 1 calc R . .
C11 C 0.9932(4) 0.76904(18) 0.1047(3) 0.0284(7) Uani 1 1 d . . .
C12 C 1.0054(4) 0.75634(19) -0.0033(3) 0.0343(8) Uani 1 1 d . . .
H12 H 1.0455 0.7056 -0.0250 0.041 Uiso 1 1 calc R . .
C13 C 0.9597(5) 0.8170(2) -0.0790(3) 0.0395(9) Uani 1 1 d . . .
H13 H 0.9668 0.8074 -0.1525 0.047 Uiso 1 1 calc R . .
C14 C 0.9032(5) 0.8923(2) -0.0484(3) 0.0418(9) Uani 1 1 d . . .
H14 H 0.8712 0.9338 -0.1006 0.050 Uiso 1 1 calc R . .
C15 C 0.8944(5) 0.9055(2) 0.0583(3) 0.0382(9) Uani 1 1 d . . .
H15 H 0.8575 0.9569 0.0797 0.046 Uiso 1 1 calc R . .
C16 C 0.9385(5) 0.84497(19) 0.1355(3) 0.0343(8) Uani 1 1 d . . .
H16 H 0.9315 0.8551 0.2090 0.041 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 C2 1.830(5) . ?
Rh1 C1 1.903(4) . ?
Rh1 C3 2.064(3) . ?
Rh1 Cl1 2.3435(12) . ?
O1 C1 1.128(4) . ?
O2 C2 1.130(5) . ?
N1 C3 1.354(4) . ?
N1 C9 1.391(4) . ?
N1 C5 1.411(4) . ?
N2 C3 1.350(4) . ?
N2 C4 1.396(4) . ?
N2 C10 1.459(4) . ?
C4 C5 1.361(5) . ?
C4 C11 1.468(4) . ?
C5 C6 1.420(5) . ?
C6 C7 1.343(5) . ?
C7 C8 1.426(5) . ?
C8 C9 1.343(5) . ?
C11 C12 1.394(5) . ?
C11 C16 1.400(4) . ?
C12 C13 1.381(5) . ?
C13 C14 1.393(5) . ?
C14 C15 1.372(6) . ?
C15 C16 1.390(5) . ?

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
C2 Rh1 C1 91.84(18) . . ?
C2 Rh1 C3 90.15(16) . . ?
C1 Rh1 C3 175.95(15) . . ?
C2 Rh1 Cl1 177.94(13) . . ?
C1 Rh1 Cl1 90.19(13) . . ?
C3 Rh1 Cl1 87.84(10) . . ?
C3 N1 C9 127.6(3) . . ?
C3 N1 C5 111.1(3) . . ?
C9 N1 C5 121.3(3) . . ?
C3 N2 C4 112.0(3) . . ?
C3 N2 C10 122.3(3) . . ?
C4 N2 C10 125.6(3) . . ?
O1 C1 Rh1 176.8(4) . . ?
O2 C2 Rh1 178.4(5) . . ?
N2 C3 N1 104.6(3) . . ?
N2 C3 Rh1 126.4(3) . . ?
N1 C3 Rh1 128.6(3) . . ?
C5 C4 N2 106.1(3) . . ?
C5 C4 C11 129.7(3) . . ?
N2 C4 C11 124.2(3) . . ?
C4 C5 N1 106.1(3) . . ?
C4 C5 C6 135.5(3) . . ?
N1 C5 C6 118.3(3) . . ?
C7 C6 C5 119.4(3) . . ?
C6 C7 C8 121.0(4) . . ?
C9 C8 C7 121.0(4) . . ?
C8 C9 N1 118.9(3) . . ?
C12 C11 C16 118.9(3) . . ?
C12 C11 C4 121.6(3) . . ?
C16 C11 C4 119.4(3) . . ?
C13 C12 C11 120.4(3) . . ?
C12 C13 C14 120.6(4) . . ?
C15 C14 C13 119.1(3) . . ?
C14 C15 C16 121.2(3) . . ?
C15 C16 C11 119.8(4) . . ?

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
C2 Rh1 C1 O1 -70(7) . . . . ?
C3 Rh1 C1 O1 49(8) . . . . ?
Cl1 Rh1 C1 O1 110(7) . . . . ?
C1 Rh1 C2 O2 -84(13) . . . . ?
C3 Rh1 C2 O2 99(13) . . . . ?
Cl1 Rh1 C2 O2 86(14) . . . . ?
C4 N2 C3 N1 -0.6(4) . . . . ?
C10 N2 C3 N1 -177.8(3) . . . . ?
C4 N2 C3 Rh1 173.5(2) . . . . ?
C10 N2 C3 Rh1 -3.7(5) . . . . ?
C9 N1 C3 N2 -178.7(3) . . . . ?
C5 N1 C3 N2 0.9(4) . . . . ?
C9 N1 C3 Rh1 7.3(6) . . . . ?
C5 N1 C3 Rh1 -173.1(3) . . . . ?
C2 Rh1 C3 N2 104.6(4) . . . . ?
C1 Rh1 C3 N2 -15(2) . . . . ?
Cl1 Rh1 C3 N2 -75.9(3) . . . . ?
C2 Rh1 C3 N1 -82.7(4) . . . . ?
C1 Rh1 C3 N1 158(2) . . . . ?
Cl1 Rh1 C3 N1 96.8(3) . . . . ?
C3 N2 C4 C5 0.1(4) . . . . ?
C10 N2 C4 C5 177.2(3) . . . . ?
C3 N2 C4 C11 179.8(3) . . . . ?
C10 N2 C4 C11 -3.1(5) . . . . ?
N2 C4 C5 N1 0.4(4) . . . . ?
C11 C4 C5 N1 -179.2(3) . . . . ?
N2 C4 C5 C6 178.6(4) . . . . ?
C11 C4 C5 C6 -1.0(7) . . . . ?
C3 N1 C5 C4 -0.8(4) . . . . ?
C9 N1 C5 C4 178.8(3) . . . . ?
C3 N1 C5 C6 -179.4(3) . . . . ?
C9 N1 C5 C6 0.2(5) . . . . ?
C4 C5 C6 C7 -177.8(4) . . . . ?
N1 C5 C6 C7 0.2(5) . . . . ?
C5 C6 C7 C8 -0.5(6) . . . . ?
C6 C7 C8 C9 0.2(7) . . . . ?
C7 C8 C9 N1 0.3(6) . . . . ?
C3 N1 C9 C8 179.1(4) . . . . ?
C5 N1 C9 C8 -0.5(5) . . . . ?
C5 C4 C11 C12 133.6(4) . . . . ?
N2 C4 C11 C12 -46.0(5) . . . . ?
C5 C4 C11 C16 -44.8(5) . . . . ?
N2 C4 C11 C16 135.7(3) . . . . ?
C16 C11 C12 C13 -1.8(5) . . . . ?
C4 C11 C12 C13 179.9(3) . . . . ?
C11 C12 C13 C14 1.0(6) . . . . ?
C12 C13 C14 C15 0.4(6) . . . . ?
C13 C14 C15 C16 -0.9(6) . . . . ?
C14 C15 C16 C11 0.1(5) . . . . ?
C12 C11 C16 C15 1.2(5) . . . . ?
C4 C11 C16 C15 179.6(3) . . . . ?

_diffrn_measured_fraction_theta_max 0.999
_diffrn_reflns_theta_full        27.50
_diffrn_measured_fraction_theta_full 0.999
_refine_diff_density_max         0.769
_refine_diff_density_min         -0.416
_refine_diff_density_rms         0.085
####################################################################### 
# 
# 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_ykc6f5rhco
_database_code_depnum_ccdc_archive 'CCDC 1515287'
_audit_update_record             
;
2016-11-07 deposited with the CCDC.
2017-01-25 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C16 H7 Cl F5 N2 O2 Rh'
_chemical_formula_sum            'C16 H7 Cl F5 N2 O2 Rh'
_chemical_formula_weight         492.60

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'
F F 0.0171 0.0103 '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           triclinic
_symmetry_space_group_name_H-M   'P -1         '
_symmetry_Int_Tables_number      2

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

_cell_length_a                   10.436(3)
_cell_length_b                   12.000(3)
_cell_length_c                   14.960(4)
_cell_angle_alpha                82.159(8)
_cell_angle_beta                 89.752(9)
_cell_angle_gamma                66.314(6)
_cell_volume                     1697.0(7)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    6379
_cell_measurement_theta_min      1.9
_cell_measurement_theta_max      30.8
_cell_measurement_temperature    123.2

_exptl_crystal_description       Block
_exptl_crystal_colour            Yellow
_exptl_crystal_size_max          0.29
_exptl_crystal_size_mid          0.17
_exptl_crystal_size_min          0.14
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.928
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             960
_exptl_absorpt_coefficient_mu    1.230
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(Jacobson, 1998)'
_exptl_absorpt_correction_T_min  0.676
_exptl_absorpt_correction_T_max  1.000

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      123(2)
_diffrn_radiation_wavelength     0.71075
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Rigaku/MSC Mercury CCD'
_diffrn_measurement_method       ω
_diffrn_detector_area_resol_mean 14.63
_diffrn_reflns_number            13809
_diffrn_reflns_av_R_equivalents  0.0392
_diffrn_reflns_av_sigmaI/netI    0.0793
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_theta_min         1.87
_diffrn_reflns_theta_max         27.50
_reflns_number_total             7738
_reflns_number_gt                5372
_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)+(0.0106P)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    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         7738
_refine_ls_number_parameters     489
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0393
_refine_ls_R_factor_gt           0.0296
_refine_ls_wR_factor_ref         0.0596
_refine_ls_wR_factor_gt          0.0571
_refine_ls_goodness_of_fit_ref   0.875
_refine_ls_restrained_S_all      0.875
_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 0.47252(2) 0.25876(2) 0.310290(15) 0.01845(6) Uani 1 1 d . . .
Rh2 Rh 0.27040(2) 0.62551(2) 0.197674(15) 0.01722(6) Uani 1 1 d . . .
Cl1 Cl 0.36275(8) 0.14488(7) 0.25199(5) 0.02337(17) Uani 1 1 d . . .
Cl2 Cl 0.03325(8) 0.69385(8) 0.23090(5) 0.0301(2) Uani 1 1 d . . .
F1 F 0.16952(18) 0.05544(16) 0.63903(11) 0.0317(5) Uani 1 1 d . . .
F2 F 0.17989(19) -0.02192(17) 0.81636(12) 0.0376(5) Uani 1 1 d . . .
F3 F 0.34073(19) 0.02747(17) 0.93315(11) 0.0385(5) Uani 1 1 d . . .
F4 F 0.48004(18) 0.16819(17) 0.87206(11) 0.0347(5) Uani 1 1 d . . .
F5 F 0.45553(18) 0.26129(16) 0.69501(11) 0.0314(5) Uani 1 1 d . . .
F6 F 0.20198(16) 0.66086(15) -0.24554(10) 0.0228(4) Uani 1 1 d . . .
F7 F 0.09370(19) 0.82878(17) -0.39341(11) 0.0343(5) Uani 1 1 d . . .
F8 F -0.13466(19) 1.04017(17) -0.38231(12) 0.0400(5) Uani 1 1 d . . .
F9 F -0.25285(17) 1.08172(16) -0.22206(12) 0.0331(5) Uani 1 1 d . . .
F10 F -0.14384(17) 0.91625(15) -0.07261(11) 0.0253(4) Uani 1 1 d . . .
O1 O 0.6032(2) 0.4005(2) 0.39571(15) 0.0366(6) Uani 1 1 d . . .
O2 O 0.6084(2) 0.2701(2) 0.13091(14) 0.0322(6) Uani 1 1 d . . .
O3 O 0.5623(2) 0.5531(2) 0.14116(16) 0.0446(7) Uani 1 1 d . . .
O4 O 0.3300(2) 0.6470(2) 0.39180(15) 0.0411(6) Uani 1 1 d . . .
N1 N 0.2194(2) 0.3088(2) 0.42708(15) 0.0184(6) Uani 1 1 d . . .
N2 N 0.4067(2) 0.1975(2) 0.50796(15) 0.0181(6) Uani 1 1 d . . .
N3 N 0.1992(2) 0.5299(2) 0.03063(15) 0.0142(5) Uani 1 1 d . . .
N4 N 0.1476(2) 0.7230(2) 0.00479(15) 0.0147(5) Uani 1 1 d . . .
C1 C 0.5544(3) 0.3459(3) 0.3621(2) 0.0242(7) Uani 1 1 d . . .
C2 C 0.5622(3) 0.2648(3) 0.1993(2) 0.0226(7) Uani 1 1 d . . .
C3 C 0.3615(3) 0.2560(3) 0.42391(19) 0.0184(7) Uani 1 1 d . . .
C4 C 0.1216(3) 0.3845(3) 0.3585(2) 0.0236(7) Uani 1 1 d . . .
H4 H 0.1513 0.4054 0.3009 0.028 Uiso 1 1 calc R . .
C5 C -0.0154(3) 0.4279(3) 0.3743(2) 0.0247(7) Uani 1 1 d . . .
H5 H -0.0826 0.4801 0.3277 0.030 Uiso 1 1 calc R . .
C6 C -0.0614(3) 0.3963(3) 0.4606(2) 0.0243(7) Uani 1 1 d . . .
H6 H -0.1588 0.4251 0.4698 0.029 Uiso 1 1 calc R . .
C7 C 0.0314(3) 0.3267(3) 0.52838(19) 0.0214(7) Uani 1 1 d . . .
H7 H 0.0000 0.3080 0.5859 0.026 Uiso 1 1 calc R . .
C8 C 0.1769(3) 0.2812(3) 0.51403(18) 0.0176(6) Uani 1 1 d . . .
C9 C 0.2976(3) 0.2106(3) 0.56463(19) 0.0189(7) Uani 1 1 d . . .
C10 C 0.5566(3) 0.1211(3) 0.5348(2) 0.0248(7) Uani 1 1 d . . .
H10 H 0.6061 0.0891 0.4819 0.037 Uiso 1 1 calc R . .
H10A H 0.5643 0.0523 0.5811 0.037 Uiso 1 1 calc R . .
H10B H 0.5985 0.1715 0.5590 0.037 Uiso 1 1 calc R . .
C11 C 0.3151(3) 0.1585(3) 0.66076(19) 0.0181(7) Uani 1 1 d . . .
C12 C 0.2464(3) 0.0858(3) 0.6945(2) 0.0204(7) Uani 1 1 d . . .
C13 C 0.2527(3) 0.0441(3) 0.7857(2) 0.0236(7) Uani 1 1 d . . .
C14 C 0.3324(3) 0.0699(3) 0.8447(2) 0.0236(7) Uani 1 1 d . . .
C15 C 0.4034(3) 0.1413(3) 0.8136(2) 0.0242(7) Uani 1 1 d . . .
C16 C 0.3919(3) 0.1860(3) 0.7236(2) 0.0206(7) Uani 1 1 d . . .
C17 C 0.4507(3) 0.5800(3) 0.1643(2) 0.0254(7) Uani 1 1 d . . .
C18 C 0.3123(3) 0.6368(3) 0.3200(2) 0.0256(7) Uani 1 1 d . . .
C19 C 0.2069(3) 0.6246(3) 0.06838(18) 0.0143(6) Uani 1 1 d . . .
C20 C 0.2469(3) 0.4069(3) 0.07067(19) 0.0171(6) Uani 1 1 d . . .
H20 H 0.2911 0.3812 0.1297 0.021 Uiso 1 1 calc R . .
C21 C 0.2289(3) 0.3257(3) 0.0237(2) 0.0203(7) Uani 1 1 d . . .
H21 H 0.2634 0.2413 0.0492 0.024 Uiso 1 1 calc R . .
C22 C 0.1588(3) 0.3645(3) -0.0634(2) 0.0214(7) Uani 1 1 d . . .
H22 H 0.1447 0.3060 -0.0945 0.026 Uiso 1 1 calc R . .
C23 C 0.1119(3) 0.4832(3) -0.10284(18) 0.0163(6) Uani 1 1 d . . .
H23 H 0.0652 0.5082 -0.1611 0.020 Uiso 1 1 calc R . .
C24 C 0.1336(3) 0.5702(3) -0.05585(18) 0.0142(6) Uani 1 1 d . . .
C25 C 0.1011(3) 0.6940(3) -0.07234(18) 0.0152(6) Uani 1 1 d . . .
C26 C 0.1387(3) 0.8442(3) 0.01894(19) 0.0228(7) Uani 1 1 d . . .
H26 H 0.0556 0.8846 0.0522 0.034 Uiso 1 1 calc R . .
H26A H 0.1319 0.8945 -0.0397 0.034 Uiso 1 1 calc R . .
H26B H 0.2228 0.8345 0.0538 0.034 Uiso 1 1 calc R . .
C27 C 0.0353(3) 0.7838(3) -0.15346(18) 0.0157(6) Uani 1 1 d . . .
C28 C 0.0889(3) 0.7647(3) -0.23758(19) 0.0179(7) Uani 1 1 d . . .
C29 C 0.0338(3) 0.8502(3) -0.31423(19) 0.0225(7) Uani 1 1 d . . .
C30 C -0.0801(3) 0.9569(3) -0.3089(2) 0.0261(8) Uani 1 1 d . . .
C31 C -0.1391(3) 0.9789(3) -0.2268(2) 0.0225(7) Uani 1 1 d . . .
C32 C -0.0809(3) 0.8922(3) -0.1517(2) 0.0189(7) 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
Rh1 C1 1.835(3) . ?
Rh1 C2 1.909(3) . ?
Rh1 C3 2.057(3) . ?
Rh1 Cl1 2.3520(8) . ?
Rh2 C17 1.825(3) . ?
Rh2 C18 1.918(3) . ?
Rh2 C19 2.050(3) . ?
Rh2 Cl2 2.3484(9) . ?
F1 C12 1.338(3) . ?
F2 C13 1.341(3) . ?
F3 C14 1.341(3) . ?
F4 C15 1.342(3) . ?
F5 C16 1.347(3) . ?
F6 C28 1.348(3) . ?
F7 C29 1.344(3) . ?
F8 C30 1.334(3) . ?
F9 C31 1.335(3) . ?
F10 C32 1.359(3) . ?
O1 C1 1.141(3) . ?
O2 C2 1.134(3) . ?
O3 C17 1.142(3) . ?
O4 C18 1.123(3) . ?
N1 C3 1.363(3) . ?
N1 C4 1.389(4) . ?
N1 C8 1.412(3) . ?
N2 C3 1.339(3) . ?
N2 C9 1.387(3) . ?
N2 C10 1.484(3) . ?
N3 C19 1.366(3) . ?
N3 C24 1.395(3) . ?
N3 C20 1.399(3) . ?
N4 C19 1.339(3) . ?
N4 C25 1.393(3) . ?
N4 C26 1.464(3) . ?
C4 C5 1.343(4) . ?
C4 H4 0.9500 . ?
C5 C6 1.430(4) . ?
C5 H5 0.9500 . ?
C6 C7 1.339(4) . ?
C6 H6 0.9500 . ?
C7 C8 1.418(4) . ?
C7 H7 0.9500 . ?
C8 C9 1.361(4) . ?
C9 C11 1.469(4) . ?
C10 H10 0.9800 . ?
C10 H10A 0.9800 . ?
C10 H10B 0.9800 . ?
C11 C12 1.382(3) . ?
C11 C16 1.393(4) . ?
C12 C13 1.379(4) . ?
C13 C14 1.362(4) . ?
C14 C15 1.378(4) . ?
C15 C16 1.366(4) . ?
C20 C21 1.347(4) . ?
C20 H20 0.9500 . ?
C21 C22 1.421(4) . ?
C21 H21 0.9500 . ?
C22 C23 1.353(4) . ?
C22 H22 0.9500 . ?
C23 C24 1.423(4) . ?
C23 H23 0.9500 . ?
C24 C25 1.371(4) . ?
C25 C27 1.470(4) . ?
C26 H26 0.9800 . ?
C26 H26A 0.9800 . ?
C26 H26B 0.9800 . ?
C27 C32 1.381(4) . ?
C27 C28 1.385(4) . ?
C28 C29 1.381(4) . ?
C29 C30 1.365(4) . ?
C30 C31 1.382(4) . ?
C31 C32 1.375(4) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C1 Rh1 C2 93.66(12) . . ?
C1 Rh1 C3 89.48(12) . . ?
C2 Rh1 C3 175.50(12) . . ?
C1 Rh1 Cl1 176.74(9) . . ?
C2 Rh1 Cl1 89.56(9) . . ?
C3 Rh1 Cl1 87.33(8) . . ?
C17 Rh2 C18 94.75(13) . . ?
C17 Rh2 C19 90.12(12) . . ?
C18 Rh2 C19 174.67(12) . . ?
C17 Rh2 Cl2 175.91(10) . . ?
C18 Rh2 Cl2 88.19(9) . . ?
C19 Rh2 Cl2 86.84(7) . . ?
C3 N1 C4 127.9(2) . . ?
C3 N1 C8 111.2(2) . . ?
C4 N1 C8 120.8(2) . . ?
C3 N2 C9 112.5(2) . . ?
C3 N2 C10 123.0(2) . . ?
C9 N2 C10 124.3(2) . . ?
C19 N3 C24 111.5(2) . . ?
C19 N3 C20 126.6(2) . . ?
C24 N3 C20 121.9(2) . . ?
C19 N4 C25 112.3(2) . . ?
C19 N4 C26 121.1(2) . . ?
C25 N4 C26 126.6(2) . . ?
O1 C1 Rh1 178.5(3) . . ?
O2 C2 Rh1 176.1(3) . . ?
N2 C3 N1 104.3(2) . . ?
N2 C3 Rh1 129.8(2) . . ?
N1 C3 Rh1 125.8(2) . . ?
C5 C4 N1 119.4(3) . . ?
C5 C4 H4 120.3 . . ?
N1 C4 H4 120.3 . . ?
C4 C5 C6 120.7(3) . . ?
C4 C5 H5 119.6 . . ?
C6 C5 H5 119.6 . . ?
C7 C6 C5 120.7(3) . . ?
C7 C6 H6 119.6 . . ?
C5 C6 H6 119.6 . . ?
C6 C7 C8 119.7(3) . . ?
C6 C7 H7 120.1 . . ?
C8 C7 H7 120.1 . . ?
C9 C8 N1 105.4(2) . . ?
C9 C8 C7 136.1(3) . . ?
N1 C8 C7 118.4(3) . . ?
C8 C9 N2 106.6(2) . . ?
C8 C9 C11 128.6(3) . . ?
N2 C9 C11 124.8(3) . . ?
N2 C10 H10 109.5 . . ?
N2 C10 H10A 109.5 . . ?
H10 C10 H10A 109.5 . . ?
N2 C10 H10B 109.5 . . ?
H10 C10 H10B 109.5 . . ?
H10A C10 H10B 109.5 . . ?
C12 C11 C16 116.3(3) . . ?
C12 C11 C9 120.8(3) . . ?
C16 C11 C9 122.7(2) . . ?
F1 C12 C13 118.0(2) . . ?
F1 C12 C11 120.4(3) . . ?
C13 C12 C11 121.6(3) . . ?
F2 C13 C14 119.8(3) . . ?
F2 C13 C12 119.9(3) . . ?
C14 C13 C12 120.3(2) . . ?
F3 C14 C13 120.4(2) . . ?
F3 C14 C15 119.8(3) . . ?
C13 C14 C15 119.8(3) . . ?
F4 C15 C16 121.0(2) . . ?
F4 C15 C14 119.7(3) . . ?
C16 C15 C14 119.3(3) . . ?
F5 C16 C15 118.6(3) . . ?
F5 C16 C11 118.8(2) . . ?
C15 C16 C11 122.6(2) . . ?
O3 C17 Rh2 178.2(3) . . ?
O4 C18 Rh2 176.5(3) . . ?
N4 C19 N3 104.3(2) . . ?
N4 C19 Rh2 126.3(2) . . ?
N3 C19 Rh2 129.03(19) . . ?
C21 C20 N3 118.6(3) . . ?
C21 C20 H20 120.7 . . ?
N3 C20 H20 120.7 . . ?
C20 C21 C22 120.9(3) . . ?
C20 C21 H21 119.6 . . ?
C22 C21 H21 119.6 . . ?
C23 C22 C21 121.1(3) . . ?
C23 C22 H22 119.4 . . ?
C21 C22 H22 119.4 . . ?
C22 C23 C24 119.1(3) . . ?
C22 C23 H23 120.4 . . ?
C24 C23 H23 120.4 . . ?
C25 C24 N3 105.8(2) . . ?
C25 C24 C23 135.8(3) . . ?
N3 C24 C23 118.4(2) . . ?
C24 C25 N4 106.1(2) . . ?
C24 C25 C27 130.1(3) . . ?
N4 C25 C27 123.8(3) . . ?
N4 C26 H26 109.5 . . ?
N4 C26 H26A 109.5 . . ?
H26 C26 H26A 109.5 . . ?
N4 C26 H26B 109.5 . . ?
H26 C26 H26B 109.5 . . ?
H26A C26 H26B 109.5 . . ?
C32 C27 C28 115.5(3) . . ?
C32 C27 C25 123.3(3) . . ?
C28 C27 C25 121.2(3) . . ?
F6 C28 C29 118.0(3) . . ?
F6 C28 C27 119.4(3) . . ?
C29 C28 C27 122.6(3) . . ?
F7 C29 C30 120.3(3) . . ?
F7 C29 C28 119.9(3) . . ?
C30 C29 C28 119.8(3) . . ?
F8 C30 C29 120.5(3) . . ?
F8 C30 C31 119.8(3) . . ?
C29 C30 C31 119.8(3) . . ?
F9 C31 C32 121.3(3) . . ?
F9 C31 C30 119.7(3) . . ?
C32 C31 C30 118.9(3) . . ?
F10 C32 C31 117.1(3) . . ?
F10 C32 C27 119.5(3) . . ?
C31 C32 C27 123.4(3) . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C2 Rh1 C1 O1 166(12) . . . . ?
C3 Rh1 C1 O1 -11(12) . . . . ?
Cl1 Rh1 C1 O1 -23(13) . . . . ?
C1 Rh1 C2 O2 -135(4) . . . . ?
C3 Rh1 C2 O2 -1(5) . . . . ?
Cl1 Rh1 C2 O2 46(4) . . . . ?
C9 N2 C3 N1 0.5(3) . . . . ?
C10 N2 C3 N1 176.8(2) . . . . ?
C9 N2 C3 Rh1 -175.2(2) . . . . ?
C10 N2 C3 Rh1 1.2(4) . . . . ?
C4 N1 C3 N2 177.1(3) . . . . ?
C8 N1 C3 N2 -0.6(3) . . . . ?
C4 N1 C3 Rh1 -7.0(4) . . . . ?
C8 N1 C3 Rh1 175.23(19) . . . . ?
C1 Rh1 C3 N2 -68.3(3) . . . . ?
C2 Rh1 C3 N2 157.3(14) . . . . ?
Cl1 Rh1 C3 N2 111.0(3) . . . . ?
C1 Rh1 C3 N1 116.9(3) . . . . ?
C2 Rh1 C3 N1 -17.5(17) . . . . ?
Cl1 Rh1 C3 N1 -63.8(2) . . . . ?
C3 N1 C4 C5 179.8(3) . . . . ?
C8 N1 C4 C5 -2.6(4) . . . . ?
N1 C4 C5 C6 -0.4(5) . . . . ?
C4 C5 C6 C7 2.6(5) . . . . ?
C5 C6 C7 C8 -1.6(5) . . . . ?
C3 N1 C8 C9 0.6(3) . . . . ?
C4 N1 C8 C9 -177.4(3) . . . . ?
C3 N1 C8 C7 -178.5(3) . . . . ?
C4 N1 C8 C7 3.6(4) . . . . ?
C6 C7 C8 C9 179.9(3) . . . . ?
C6 C7 C8 N1 -1.4(4) . . . . ?
N1 C8 C9 N2 -0.3(3) . . . . ?
C7 C8 C9 N2 178.5(3) . . . . ?
N1 C8 C9 C11 178.5(3) . . . . ?
C7 C8 C9 C11 -2.7(6) . . . . ?
C3 N2 C9 C8 -0.1(3) . . . . ?
C10 N2 C9 C8 -176.4(3) . . . . ?
C3 N2 C9 C11 -179.0(3) . . . . ?
C10 N2 C9 C11 4.7(5) . . . . ?
C8 C9 C11 C12 54.8(4) . . . . ?
N2 C9 C11 C12 -126.6(3) . . . . ?
C8 C9 C11 C16 -120.4(4) . . . . ?
N2 C9 C11 C16 58.2(4) . . . . ?
C16 C11 C12 F1 179.6(3) . . . . ?
C9 C11 C12 F1 4.2(4) . . . . ?
C16 C11 C12 C13 0.7(4) . . . . ?
C9 C11 C12 C13 -174.8(3) . . . . ?
F1 C12 C13 F2 -1.8(4) . . . . ?
C11 C12 C13 F2 177.2(3) . . . . ?
F1 C12 C13 C14 178.3(3) . . . . ?
C11 C12 C13 C14 -2.7(5) . . . . ?
F2 C13 C14 F3 1.3(4) . . . . ?
C12 C13 C14 F3 -178.8(3) . . . . ?
F2 C13 C14 C15 -177.8(3) . . . . ?
C12 C13 C14 C15 2.1(5) . . . . ?
F3 C14 C15 F4 -0.2(4) . . . . ?
C13 C14 C15 F4 178.9(3) . . . . ?
F3 C14 C15 C16 -178.7(3) . . . . ?
C13 C14 C15 C16 0.4(5) . . . . ?
F4 C15 C16 F5 -2.2(4) . . . . ?
C14 C15 C16 F5 176.3(3) . . . . ?
F4 C15 C16 C11 179.0(3) . . . . ?
C14 C15 C16 C11 -2.5(5) . . . . ?
C12 C11 C16 F5 -176.9(3) . . . . ?
C9 C11 C16 F5 -1.5(4) . . . . ?
C12 C11 C16 C15 1.9(4) . . . . ?
C9 C11 C16 C15 177.3(3) . . . . ?
C18 Rh2 C17 O3 -147(10) . . . . ?
C19 Rh2 C17 O3 30(10) . . . . ?
Cl2 Rh2 C17 O3 -12(11) . . . . ?
C17 Rh2 C18 O4 159(5) . . . . ?
C19 Rh2 C18 O4 3(5) . . . . ?
Cl2 Rh2 C18 O4 -18(5) . . . . ?
C25 N4 C19 N3 0.6(3) . . . . ?
C26 N4 C19 N3 -178.5(2) . . . . ?
C25 N4 C19 Rh2 -172.71(17) . . . . ?
C26 N4 C19 Rh2 8.3(3) . . . . ?
C24 N3 C19 N4 -0.7(3) . . . . ?
C20 N3 C19 N4 -179.8(2) . . . . ?
C24 N3 C19 Rh2 172.27(17) . . . . ?
C20 N3 C19 Rh2 -6.8(4) . . . . ?
C17 Rh2 C19 N4 -99.3(2) . . . . ?
C18 Rh2 C19 N4 56.8(12) . . . . ?
Cl2 Rh2 C19 N4 78.0(2) . . . . ?
C17 Rh2 C19 N3 89.1(2) . . . . ?
C18 Rh2 C19 N3 -114.7(11) . . . . ?
Cl2 Rh2 C19 N3 -93.6(2) . . . . ?
C19 N3 C20 C21 179.1(2) . . . . ?
C24 N3 C20 C21 0.2(4) . . . . ?
N3 C20 C21 C22 -2.0(4) . . . . ?
C20 C21 C22 C23 2.0(4) . . . . ?
C21 C22 C23 C24 0.1(4) . . . . ?
C19 N3 C24 C25 0.6(3) . . . . ?
C20 N3 C24 C25 179.7(2) . . . . ?
C19 N3 C24 C23 -177.3(2) . . . . ?
C20 N3 C24 C23 1.8(3) . . . . ?
C22 C23 C24 C25 -179.0(3) . . . . ?
C22 C23 C24 N3 -1.9(4) . . . . ?
N3 C24 C25 N4 -0.3(3) . . . . ?
C23 C24 C25 N4 177.1(3) . . . . ?
N3 C24 C25 C27 177.8(2) . . . . ?
C23 C24 C25 C27 -4.8(5) . . . . ?
C19 N4 C25 C24 -0.2(3) . . . . ?
C26 N4 C25 C24 178.8(2) . . . . ?
C19 N4 C25 C27 -178.4(2) . . . . ?
C26 N4 C25 C27 0.6(4) . . . . ?
C24 C25 C27 C32 127.2(3) . . . . ?
N4 C25 C27 C32 -55.1(4) . . . . ?
C24 C25 C27 C28 -53.8(4) . . . . ?
N4 C25 C27 C28 124.0(3) . . . . ?
C32 C27 C28 F6 -179.7(2) . . . . ?
C25 C27 C28 F6 1.2(4) . . . . ?
C32 C27 C28 C29 2.4(4) . . . . ?
C25 C27 C28 C29 -176.7(2) . . . . ?
F6 C28 C29 F7 -0.6(4) . . . . ?
C27 C28 C29 F7 177.3(2) . . . . ?
F6 C28 C29 C30 -179.5(2) . . . . ?
C27 C28 C29 C30 -1.6(4) . . . . ?
F7 C29 C30 F8 1.2(4) . . . . ?
C28 C29 C30 F8 -179.9(2) . . . . ?
F7 C29 C30 C31 -178.7(2) . . . . ?
C28 C29 C30 C31 0.2(4) . . . . ?
F8 C30 C31 F9 2.0(4) . . . . ?
C29 C30 C31 F9 -178.1(2) . . . . ?
F8 C30 C31 C32 -179.7(2) . . . . ?
C29 C30 C31 C32 0.2(4) . . . . ?
F9 C31 C32 F10 -0.4(4) . . . . ?
C30 C31 C32 F10 -178.7(2) . . . . ?
F9 C31 C32 C27 179.0(2) . . . . ?
C30 C31 C32 C27 0.7(4) . . . . ?
C28 C27 C32 F10 177.4(2) . . . . ?
C25 C27 C32 F10 -3.5(4) . . . . ?
C28 C27 C32 C31 -2.0(4) . . . . ?
C25 C27 C32 C31 177.1(3) . . . . ?

_diffrn_measured_fraction_theta_max 0.991
_diffrn_reflns_theta_full        27.50
_diffrn_measured_fraction_theta_full 0.991
_refine_diff_density_max         0.743
_refine_diff_density_min         -0.881
_refine_diff_density_rms         0.096
####################################################################### 
# 
# 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_ykro
_database_code_depnum_ccdc_archive 'CCDC 1515286'
_audit_update_record             
;
2016-11-07 deposited with the CCDC.
2017-01-25 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C19 H11 Cl F3 N2 O2 Rh'
_chemical_formula_sum            'C19 H11 Cl F3 N2 O2 Rh'
_chemical_formula_weight         494.66

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'
F F 0.0171 0.0103 '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'

_symmetry_cell_setting           triclinic
_symmetry_space_group_name_H-M   'P -1          '
_symmetry_Int_Tables_number      2

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

_cell_length_a                   7.168(4)
_cell_length_b                   9.002(5)
_cell_length_c                   15.020(8)
_cell_angle_alpha                76.479(14)
_cell_angle_beta                 80.476(18)
_cell_angle_gamma                81.147(16)
_cell_volume                     922.6(8)
_cell_formula_units_Z            2
_cell_measurement_temperature    123(2)
_cell_measurement_reflns_used    3071
_cell_measurement_theta_min      2.3
_cell_measurement_theta_max      30.9

_exptl_crystal_description       Block
_exptl_crystal_colour            Yellow
_exptl_crystal_size_max          0.29
_exptl_crystal_size_mid          0.23
_exptl_crystal_size_min          0.20
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.781
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             488
_exptl_absorpt_coefficient_mu    1.117
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(Jacobson, 1998)'
_exptl_absorpt_correction_T_min  0.727
_exptl_absorpt_correction_T_max  1.000

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      123(2)
_diffrn_radiation_wavelength     0.71075
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Rigaku/MSC Mercury CCD'
_diffrn_measurement_method       ω
_diffrn_detector_area_resol_mean 14.63
_diffrn_reflns_number            7286
_diffrn_reflns_av_R_equivalents  0.0396
_diffrn_reflns_av_sigmaI/netI    0.0758
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_theta_min         1.41
_diffrn_reflns_theta_max         27.50
_reflns_number_total             4171
_reflns_number_gt                3383
_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)+(0.0452P)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    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         4171
_refine_ls_number_parameters     254
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0556
_refine_ls_R_factor_gt           0.0446
_refine_ls_wR_factor_ref         0.1097
_refine_ls_wR_factor_gt          0.1025
_refine_ls_goodness_of_fit_ref   1.010
_refine_ls_restrained_S_all      1.010
_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 0.58101(4) 0.88980(4) 0.72658(2) 0.02723(12) Uani 1 1 d . . .
Cl1 Cl 0.78709(15) 0.88792(12) 0.83479(7) 0.0344(2) Uani 1 1 d . . .
F1 F -0.4516(4) 0.6751(4) 1.4890(2) 0.0686(10) Uani 1 1 d . . .
F2 F -0.1828(4) 0.7164(4) 1.51618(19) 0.0631(9) Uani 1 1 d . . .
F3 F -0.2520(5) 0.4866(4) 1.54397(19) 0.0617(9) Uani 1 1 d . . .
O1 O 0.3022(5) 0.8983(4) 0.6003(2) 0.0511(9) Uani 1 1 d . . .
O2 O 0.8252(5) 1.1018(4) 0.5839(2) 0.0542(10) Uani 1 1 d . . .
N1 N 0.4598(4) 0.5762(3) 0.8265(2) 0.0222(7) Uani 1 1 d . . .
N2 N 0.3220(4) 0.7454(3) 0.9017(2) 0.0226(7) Uani 1 1 d . . .
C1 C 0.4129(6) 0.8951(5) 0.6466(3) 0.0348(10) Uani 1 1 d . . .
C2 C 0.7315(7) 1.0263(5) 0.6361(3) 0.0365(10) Uani 1 1 d . . .
C3 C 0.4375(5) 0.7320(4) 0.8236(3) 0.0227(8) Uani 1 1 d . . .
C4 C 0.2744(5) 0.6055(4) 0.9550(3) 0.0249(8) Uani 1 1 d . . .
C5 C 0.3640(5) 0.4952(4) 0.9074(3) 0.0223(8) Uani 1 1 d . . .
C6 C 0.3798(5) 0.3330(4) 0.9238(3) 0.0272(9) Uani 1 1 d . . .
H6 H 0.3197 0.2757 0.9797 0.033 Uiso 1 1 calc R . .
C7 C 0.4810(6) 0.2612(5) 0.8593(3) 0.0323(10) Uani 1 1 d . . .
H7 H 0.4952 0.1520 0.8704 0.039 Uiso 1 1 calc R . .
C8 C 0.5669(5) 0.3462(5) 0.7749(3) 0.0300(9) Uani 1 1 d . . .
H8 H 0.6303 0.2935 0.7285 0.036 Uiso 1 1 calc R . .
C9 C 0.5604(5) 0.5014(5) 0.7589(3) 0.0267(9) Uani 1 1 d . . .
H9 H 0.6229 0.5574 0.7032 0.032 Uiso 1 1 calc R . .
C10 C 0.2500(6) 0.8935(4) 0.9273(3) 0.0318(9) Uani 1 1 d . . .
H10 H 0.2916 0.9775 0.8769 0.048 Uiso 1 1 calc R . .
H10A H 0.3000 0.8979 0.9834 0.048 Uiso 1 1 calc R . .
H10B H 0.1105 0.9041 0.9387 0.048 Uiso 1 1 calc R . .
C11 C 0.1626(5) 0.5912(5) 1.0430(3) 0.0257(8) Uani 1 1 d . . .
C12 C 0.0754(5) 0.5886(5) 1.1169(3) 0.0275(9) Uani 1 1 d . . .
C13 C -0.0186(5) 0.5917(5) 1.2087(3) 0.0249(8) Uani 1 1 d . . .
C14 C -0.0474(5) 0.7340(5) 1.2359(3) 0.0306(9) Uani 1 1 d . . .
H14 H -0.0116 0.8244 1.1934 0.037 Uiso 1 1 calc R . .
C15 C -0.1276(6) 0.7401(5) 1.3244(3) 0.0328(10) Uani 1 1 d . . .
H15 H -0.1469 0.8356 1.3434 0.039 Uiso 1 1 calc R . .
C16 C -0.1811(5) 0.6089(5) 1.3869(3) 0.0308(9) Uani 1 1 d . . .
C17 C -0.1530(5) 0.4691(5) 1.3604(3) 0.0316(9) Uani 1 1 d . . .
H17 H -0.1887 0.3791 1.4033 0.038 Uiso 1 1 calc R . .
C18 C -0.0724(5) 0.4608(5) 1.2710(3) 0.0278(9) Uani 1 1 d . . .
H18 H -0.0540 0.3651 1.2524 0.033 Uiso 1 1 calc R . .
C19 C -0.2658(6) 0.6198(6) 1.4834(3) 0.0428(12) 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
Rh1 C1 1.826(4) . ?
Rh1 C2 1.913(5) . ?
Rh1 C3 2.046(4) . ?
Rh1 Cl1 2.3660(13) . ?
F1 C19 1.345(5) . ?
F2 C19 1.344(5) . ?
F3 C19 1.326(6) . ?
O1 C1 1.131(5) . ?
O2 C2 1.116(6) . ?
N1 C3 1.378(5) . ?
N1 C9 1.389(5) . ?
N1 C5 1.394(5) . ?
N2 C3 1.338(5) . ?
N2 C4 1.383(5) . ?
N2 C10 1.467(5) . ?
C4 C5 1.376(5) . ?
C4 C11 1.417(5) . ?
C5 C6 1.413(5) . ?
C6 C7 1.342(6) . ?
C7 C8 1.416(6) . ?
C8 C9 1.356(5) . ?
C11 C12 1.177(6) . ?
C12 C13 1.436(5) . ?
C13 C18 1.384(6) . ?
C13 C14 1.409(5) . ?
C14 C15 1.369(6) . ?
C15 C16 1.388(6) . ?
C16 C17 1.383(6) . ?
C16 C19 1.495(6) . ?
C17 C18 1.386(5) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C1 Rh1 C2 92.17(19) . . ?
C1 Rh1 C3 89.90(17) . . ?
C2 Rh1 C3 175.76(16) . . ?
C1 Rh1 Cl1 177.32(14) . . ?
C2 Rh1 Cl1 89.11(12) . . ?
C3 Rh1 Cl1 88.98(10) . . ?
C3 N1 C9 126.9(4) . . ?
C3 N1 C5 111.9(3) . . ?
C9 N1 C5 121.3(3) . . ?
C3 N2 C4 113.0(3) . . ?
C3 N2 C10 123.5(3) . . ?
C4 N2 C10 123.4(3) . . ?
O1 C1 Rh1 176.9(4) . . ?
O2 C2 Rh1 177.3(4) . . ?
N2 C3 N1 103.5(3) . . ?
N2 C3 Rh1 131.2(3) . . ?
N1 C3 Rh1 125.0(3) . . ?
C5 C4 N2 106.4(3) . . ?
C5 C4 C11 130.7(4) . . ?
N2 C4 C11 122.8(3) . . ?
C4 C5 N1 105.2(3) . . ?
C4 C5 C6 135.4(4) . . ?
N1 C5 C6 119.4(4) . . ?
C7 C6 C5 119.0(4) . . ?
C6 C7 C8 120.8(4) . . ?
C9 C8 C7 121.4(4) . . ?
C8 C9 N1 118.0(4) . . ?
C12 C11 C4 175.0(4) . . ?
C11 C12 C13 175.2(4) . . ?
C18 C13 C14 120.1(4) . . ?
C18 C13 C12 122.6(4) . . ?
C14 C13 C12 117.3(4) . . ?
C15 C14 C13 119.0(4) . . ?
C14 C15 C16 120.9(4) . . ?
C17 C16 C15 120.1(4) . . ?
C17 C16 C19 120.5(4) . . ?
C15 C16 C19 119.3(4) . . ?
C16 C17 C18 119.7(4) . . ?
C13 C18 C17 120.1(4) . . ?
F3 C19 F2 105.9(4) . . ?
F3 C19 F1 106.8(4) . . ?
F2 C19 F1 105.3(4) . . ?
F3 C19 C16 113.8(4) . . ?
F2 C19 C16 112.4(4) . . ?
F1 C19 C16 112.1(4) . . ?

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
C2 Rh1 C1 O1 -142(7) . . . . ?
C3 Rh1 C1 O1 42(7) . . . . ?
Cl1 Rh1 C1 O1 -24(9) . . . . ?
C1 Rh1 C2 O2 -128(8) . . . . ?
C3 Rh1 C2 O2 -9(9) . . . . ?
Cl1 Rh1 C2 O2 55(8) . . . . ?
C4 N2 C3 N1 1.7(4) . . . . ?
C10 N2 C3 N1 -177.2(3) . . . . ?
C4 N2 C3 Rh1 -171.4(2) . . . . ?
C10 N2 C3 Rh1 9.8(5) . . . . ?
C9 N1 C3 N2 176.8(3) . . . . ?
C5 N1 C3 N2 -2.2(4) . . . . ?
C9 N1 C3 Rh1 -9.6(5) . . . . ?
C5 N1 C3 Rh1 171.5(2) . . . . ?
C1 Rh1 C3 N2 -106.6(3) . . . . ?
C2 Rh1 C3 N2 134.2(18) . . . . ?
Cl1 Rh1 C3 N2 70.9(3) . . . . ?
C1 Rh1 C3 N1 81.6(3) . . . . ?
C2 Rh1 C3 N1 -38(2) . . . . ?
Cl1 Rh1 C3 N1 -100.8(3) . . . . ?
C3 N2 C4 C5 -0.6(4) . . . . ?
C10 N2 C4 C5 178.2(3) . . . . ?
C3 N2 C4 C11 176.3(3) . . . . ?
C10 N2 C4 C11 -4.9(5) . . . . ?
N2 C4 C5 N1 -0.7(3) . . . . ?
C11 C4 C5 N1 -177.3(3) . . . . ?
N2 C4 C5 C6 177.5(3) . . . . ?
C11 C4 C5 C6 1.0(6) . . . . ?
C3 N1 C5 C4 1.8(4) . . . . ?
C9 N1 C5 C4 -177.2(3) . . . . ?
C3 N1 C5 C6 -176.8(3) . . . . ?
C9 N1 C5 C6 4.2(4) . . . . ?
C4 C5 C6 C7 179.3(4) . . . . ?
N1 C5 C6 C7 -2.6(5) . . . . ?
C5 C6 C7 C8 -1.6(5) . . . . ?
C6 C7 C8 C9 4.4(5) . . . . ?
C7 C8 C9 N1 -2.7(5) . . . . ?
C3 N1 C9 C8 179.6(3) . . . . ?
C5 N1 C9 C8 -1.6(5) . . . . ?
C5 C4 C11 C12 145(4) . . . . ?
N2 C4 C11 C12 -31(5) . . . . ?
C4 C11 C12 C13 -26(9) . . . . ?
C11 C12 C13 C18 -126(5) . . . . ?
C11 C12 C13 C14 51(5) . . . . ?
C18 C13 C14 C15 0.4(5) . . . . ?
C12 C13 C14 C15 -176.7(3) . . . . ?
C13 C14 C15 C16 -0.3(5) . . . . ?
C14 C15 C16 C17 0.3(6) . . . . ?
C14 C15 C16 C19 179.2(4) . . . . ?
C15 C16 C17 C18 -0.4(6) . . . . ?
C19 C16 C17 C18 -179.3(4) . . . . ?
C14 C13 C18 C17 -0.6(5) . . . . ?
C12 C13 C18 C17 176.3(3) . . . . ?
C16 C17 C18 C13 0.6(5) . . . . ?
C17 C16 C19 F3 20.4(5) . . . . ?
C15 C16 C19 F3 -158.4(4) . . . . ?
C17 C16 C19 F2 140.8(4) . . . . ?
C15 C16 C19 F2 -38.1(5) . . . . ?
C17 C16 C19 F1 -100.9(5) . . . . ?
C15 C16 C19 F1 80.2(5) . . . . ?

_diffrn_measured_fraction_theta_max 0.983
_diffrn_reflns_theta_full        27.50
_diffrn_measured_fraction_theta_full 0.983
_refine_diff_density_max         1.171
_refine_diff_density_min         -0.931
_refine_diff_density_rms         0.115
####################################################################### 
# 
# 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_yk465
_database_code_depnum_ccdc_archive 'CCDC 1515289'
_audit_update_record             
;
2016-11-07 deposited with the CCDC.
2017-01-25 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C15 H14 N2 O Se'
_chemical_formula_sum            'C15 H14 N2 O Se'
_chemical_formula_weight         317.24

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'
Se Se -0.0929 2.2259 '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                   8.144(2)
_cell_length_b                   9.039(3)
_cell_length_c                   9.707(3)
_cell_angle_alpha                97.961(2)
_cell_angle_beta                 106.050(4)
_cell_angle_gamma                95.085(3)
_cell_volume                     674.0(3)
_cell_formula_units_Z            2
_cell_measurement_temperature    193(2)
_cell_measurement_reflns_used    2657
_cell_measurement_theta_min      2.2155
_cell_measurement_theta_max      30.8409

_exptl_crystal_description       block
_exptl_crystal_colour            yellow
_exptl_crystal_size_max          0.51
_exptl_crystal_size_mid          0.31
_exptl_crystal_size_min          0.31
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.563
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             320
_exptl_absorpt_coefficient_mu    2.778
_exptl_absorpt_correction_type   Multi-scan
_exptl_absorpt_correction_T_min  0.3315
_exptl_absorpt_correction_T_max  0.4797
_exptl_absorpt_process_details   '(Higashi, 1999)'

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      193(2)
_diffrn_radiation_wavelength     0.71075
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Rigaku/MSC Mercury CCD'
_diffrn_measurement_method       ω
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            5428
_diffrn_reflns_av_R_equivalents  0.0268
_diffrn_reflns_av_sigmaI/netI    0.0472
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_theta_min         2.22
_diffrn_reflns_theta_max         27.50
_reflns_number_total             3060
_reflns_number_gt                2607
_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)+(0.0447P)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    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         3060
_refine_ls_number_parameters     174
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0367
_refine_ls_R_factor_gt           0.0330
_refine_ls_wR_factor_ref         0.0828
_refine_ls_wR_factor_gt          0.0817
_refine_ls_goodness_of_fit_ref   1.000
_refine_ls_restrained_S_all      1.000
_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
C1 C 0.3828(3) 0.1553(2) 0.8145(2) 0.0238(4) Uani 1 1 d . . .
N1 N 0.4323(2) 0.0358(2) 0.7365(2) 0.0246(4) Uani 1 1 d . . .
C2 C 0.5938(3) 0.0078(2) 0.8065(2) 0.0253(5) Uani 1 1 d . . .
N2 N 0.6455(2) 0.1111(2) 0.9323(2) 0.0233(4) Uani 1 1 d . . .
C3 C 0.8026(3) 0.1334(3) 1.0400(3) 0.0279(5) Uani 1 1 d . . .
H3 H 0.8866 0.0681 1.0344 0.033 Uiso 1 1 calc R . .
C4 C 0.8350(3) 0.2462(3) 1.1510(3) 0.0317(5) Uani 1 1 d . . .
H4 H 0.9430 0.2621 1.2243 0.038 Uiso 1 1 calc R . .
C5 C 0.7070(3) 0.3452(3) 1.1612(3) 0.0334(5) Uani 1 1 d . . .
H5 H 0.7318 0.4261 1.2407 0.040 Uiso 1 1 calc R . .
C6 C 0.5526(3) 0.3234(3) 1.0585(3) 0.0291(5) Uani 1 1 d . . .
H6 H 0.4682 0.3874 1.0668 0.035 Uiso 1 1 calc R . .
C7 C 0.5169(3) 0.2046(2) 0.9385(2) 0.0238(4) Uani 1 1 d . . .
Se1 Se 0.71774(3) -0.13531(3) 0.74760(3) 0.03532(11) Uani 1 1 d . . .
C8 C 0.3232(3) -0.0586(3) 0.6023(3) 0.0325(5) Uani 1 1 d . . .
H8 H 0.3390 -0.0160 0.5186 0.049 Uiso 1 1 calc R . .
H8A H 0.2022 -0.0622 0.6011 0.049 Uiso 1 1 calc R . .
H8B H 0.3552 -0.1607 0.5971 0.049 Uiso 1 1 calc R . .
C9 C 0.2224(3) 0.2211(2) 0.7623(2) 0.0244(5) Uani 1 1 d . . .
C10 C 0.1225(3) 0.2560(3) 0.8536(3) 0.0281(5) Uani 1 1 d . . .
H10 H 0.1555 0.2330 0.9493 0.034 Uiso 1 1 calc R . .
C11 C -0.0257(3) 0.3244(3) 0.8081(3) 0.0297(5) Uani 1 1 d . . .
H11 H -0.0928 0.3479 0.8722 0.036 Uiso 1 1 calc R . .
C12 C -0.0743(3) 0.3578(2) 0.6683(3) 0.0265(5) Uani 1 1 d . . .
C13 C 0.0266(3) 0.3252(2) 0.5761(3) 0.0265(5) Uani 1 1 d . . .
H13 H -0.0055 0.3497 0.4810 0.032 Uiso 1 1 calc R . .
C14 C 0.1734(3) 0.2574(2) 0.6222(2) 0.0261(5) Uani 1 1 d . . .
H14 H 0.2414 0.2354 0.5586 0.031 Uiso 1 1 calc R . .
O1 O -0.21739(19) 0.42354(19) 0.6109(2) 0.0359(4) Uani 1 1 d . . .
C15 C -0.3385(3) 0.4371(4) 0.6914(4) 0.0511(8) Uani 1 1 d . . .
H15 H -0.3802 0.3370 0.7057 0.077 Uiso 1 1 calc R . .
H15A H -0.4358 0.4829 0.6378 0.077 Uiso 1 1 calc R . .
H15B H -0.2829 0.5008 0.7862 0.077 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
C1 C7 1.371(3) . ?
C1 N1 1.386(3) . ?
C1 C9 1.474(3) . ?
N1 C2 1.366(3) . ?
N1 C8 1.460(3) . ?
C2 N2 1.368(3) . ?
C2 Se1 1.834(2) . ?
N2 C3 1.388(3) . ?
N2 C7 1.412(3) . ?
C3 C4 1.327(3) . ?
C4 C5 1.447(3) . ?
C5 C6 1.350(3) . ?
C6 C7 1.416(3) . ?
C9 C10 1.383(3) . ?
C9 C14 1.401(3) . ?
C10 C11 1.396(3) . ?
C11 C12 1.388(3) . ?
C12 O1 1.370(3) . ?
C12 C13 1.393(3) . ?
C13 C14 1.384(3) . ?
O1 C15 1.421(3) . ?

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 C1 N1 106.58(18) . . ?
C7 C1 C9 128.5(2) . . ?
N1 C1 C9 124.71(19) . . ?
C2 N1 C1 111.66(18) . . ?
C2 N1 C8 122.90(19) . . ?
C1 N1 C8 125.26(18) . . ?
N1 C2 N2 104.87(19) . . ?
N1 C2 Se1 128.48(17) . . ?
N2 C2 Se1 126.65(17) . . ?
C2 N2 C3 127.97(19) . . ?
C2 N2 C7 110.38(18) . . ?
C3 N2 C7 121.58(19) . . ?
C4 C3 N2 119.8(2) . . ?
C3 C4 C5 120.4(2) . . ?
C6 C5 C4 120.5(2) . . ?
C5 C6 C7 119.8(2) . . ?
C1 C7 N2 106.50(19) . . ?
C1 C7 C6 135.5(2) . . ?
N2 C7 C6 118.0(2) . . ?
C10 C9 C14 118.7(2) . . ?
C10 C9 C1 120.6(2) . . ?
C14 C9 C1 120.61(19) . . ?
C9 C10 C11 121.3(2) . . ?
C12 C11 C10 119.4(2) . . ?
O1 C12 C11 124.8(2) . . ?
O1 C12 C13 115.4(2) . . ?
C11 C12 C13 119.8(2) . . ?
C14 C13 C12 120.4(2) . . ?
C13 C14 C9 120.4(2) . . ?
C12 O1 C15 117.42(19) . . ?

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
C7 C1 N1 C2 -0.3(2) . . . . ?
C9 C1 N1 C2 174.59(19) . . . . ?
C7 C1 N1 C8 174.94(19) . . . . ?
C9 C1 N1 C8 -10.2(3) . . . . ?
C1 N1 C2 N2 0.8(2) . . . . ?
C8 N1 C2 N2 -174.54(18) . . . . ?
C1 N1 C2 Se1 -179.01(15) . . . . ?
C8 N1 C2 Se1 5.7(3) . . . . ?
N1 C2 N2 C3 -177.93(18) . . . . ?
Se1 C2 N2 C3 1.9(3) . . . . ?
N1 C2 N2 C7 -1.0(2) . . . . ?
Se1 C2 N2 C7 178.78(14) . . . . ?
C2 N2 C3 C4 175.6(2) . . . . ?
C7 N2 C3 C4 -1.0(3) . . . . ?
N2 C3 C4 C5 0.7(3) . . . . ?
C3 C4 C5 C6 0.5(3) . . . . ?
C4 C5 C6 C7 -1.3(3) . . . . ?
N1 C1 C7 N2 -0.4(2) . . . . ?
C9 C1 C7 N2 -174.98(19) . . . . ?
N1 C1 C7 C6 176.9(2) . . . . ?
C9 C1 C7 C6 2.3(4) . . . . ?
C2 N2 C7 C1 0.9(2) . . . . ?
C3 N2 C7 C1 178.03(18) . . . . ?
C2 N2 C7 C6 -176.94(17) . . . . ?
C3 N2 C7 C6 0.2(3) . . . . ?
C5 C6 C7 C1 -176.1(2) . . . . ?
C5 C6 C7 N2 0.9(3) . . . . ?
C7 C1 C9 C10 -50.3(3) . . . . ?
N1 C1 C9 C10 136.0(2) . . . . ?
C7 C1 C9 C14 126.0(2) . . . . ?
N1 C1 C9 C14 -47.7(3) . . . . ?
C14 C9 C10 C11 0.8(3) . . . . ?
C1 C9 C10 C11 177.2(2) . . . . ?
C9 C10 C11 C12 0.1(3) . . . . ?
C10 C11 C12 O1 179.5(2) . . . . ?
C10 C11 C12 C13 -1.1(3) . . . . ?
O1 C12 C13 C14 -179.41(19) . . . . ?
C11 C12 C13 C14 1.1(3) . . . . ?
C12 C13 C14 C9 -0.1(3) . . . . ?
C10 C9 C14 C13 -0.8(3) . . . . ?
C1 C9 C14 C13 -177.18(19) . . . . ?
C11 C12 O1 C15 -10.2(3) . . . . ?
C13 C12 O1 C15 170.3(2) . . . . ?

_diffrn_measured_fraction_theta_max 0.986
_diffrn_reflns_theta_full        27.50
_diffrn_measured_fraction_theta_full 0.986
_refine_diff_density_max         0.843
_refine_diff_density_min         -0.745
_refine_diff_density_rms         0.082
####################################################################### 
# 
# 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_azaccphrhco
_database_code_depnum_ccdc_archive 'CCDC 1515288'
_audit_update_record             
;
2016-11-07 deposited with the CCDC.
2017-01-25 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C18 H12 Cl N2 O2 Rh'
_chemical_formula_sum            'C18 H12 Cl N2 O2 Rh'
_chemical_formula_weight         426.66

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'
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'

_symmetry_cell_setting           triclinic
_symmetry_space_group_name_H-M   'P -1         '
_symmetry_Int_Tables_number      2

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

_cell_length_a                   7.0475(15)
_cell_length_b                   9.2569(18)
_cell_length_c                   14.015(3)
_cell_angle_alpha                95.006(2)
_cell_angle_beta                 104.3135(19)
_cell_angle_gamma                101.011(3)
_cell_volume                     860.9(3)
_cell_formula_units_Z            2
_cell_measurement_temperature    193(2)
_cell_measurement_reflns_used    3123
_cell_measurement_theta_min      2.3
_cell_measurement_theta_max      31.0

_exptl_crystal_description       Block
_exptl_crystal_colour            Yellow
_exptl_crystal_size_max          0.15
_exptl_crystal_size_mid          0.10
_exptl_crystal_size_min          0.05
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.646
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             424
_exptl_absorpt_coefficient_mu    1.158
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(Jacobson, 1998)'
_exptl_absorpt_correction_T_min  0.371
_exptl_absorpt_correction_T_max  0.561

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      193(2)
_diffrn_radiation_wavelength     0.71075
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Rigaku/MSC Mercury CCD'
_diffrn_measurement_method       ω
_diffrn_detector_area_resol_mean 14.63
_diffrn_reflns_number            6785
_diffrn_reflns_av_R_equivalents  0.0225
_diffrn_reflns_av_sigmaI/netI    0.0372
_diffrn_reflns_limit_h_min       -5
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_theta_min         2.26
_diffrn_reflns_theta_max         27.50
_reflns_number_total             3874
_reflns_number_gt                3522
_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)+(0.0434P)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    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         3874
_refine_ls_number_parameters     218
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0308
_refine_ls_R_factor_gt           0.0283
_refine_ls_wR_factor_ref         0.0727
_refine_ls_wR_factor_gt          0.0716
_refine_ls_goodness_of_fit_ref   1.009
_refine_ls_restrained_S_all      1.009
_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 0.84176(3) 0.609179(16) 0.725434(12) 0.02961(8) Uani 1 1 d . . .
Cl1 Cl 1.15110(10) 0.61376(7) 0.84050(5) 0.04266(15) Uani 1 1 d . . .
O1 O 0.9584(3) 0.4015(2) 0.58075(15) 0.0575(5) Uani 1 1 d . . .
O2 O 0.4426(4) 0.5948(3) 0.58950(19) 0.0747(7) Uani 1 1 d . . .
N1 N 0.7451(3) 0.74269(18) 0.91282(13) 0.0281(4) Uani 1 1 d . . .
N2 N 0.7940(2) 0.90856(17) 0.81887(13) 0.0235(3) Uani 1 1 d . . .
C1 C 0.9128(4) 0.4772(3) 0.63400(19) 0.0391(6) Uani 1 1 d . . .
C2 C 0.5956(4) 0.6015(3) 0.6402(2) 0.0449(6) Uani 1 1 d . . .
C3 C 0.7835(3) 0.7597(2) 0.82478(16) 0.0257(4) Uani 1 1 d . . .
C4 C 0.7353(3) 0.8761(2) 0.96432(16) 0.0276(4) Uani 1 1 d . . .
C5 C 0.7683(3) 0.9823(2) 0.90401(16) 0.0260(4) Uani 1 1 d . . .
C6 C 0.7857(3) 1.1386(2) 0.91285(19) 0.0337(5) Uani 1 1 d . . .
H6 H 0.7739 1.1922 0.9713 0.040 Uiso 1 1 calc R . .
C7 C 0.8192(4) 1.2090(2) 0.8365(2) 0.0393(6) Uani 1 1 d . . .
H7 H 0.8321 1.3137 0.8415 0.047 Uiso 1 1 calc R . .
C8 C 0.8356(3) 1.1294(2) 0.7487(2) 0.0358(5) Uani 1 1 d . . .
H8 H 0.8538 1.1809 0.6948 0.043 Uiso 1 1 calc R . .
C9 C 0.8257(3) 0.9825(2) 0.74072(17) 0.0291(5) Uani 1 1 d . . .
H9 H 0.8403 0.9303 0.6825 0.035 Uiso 1 1 calc R . .
C10 C 0.7168(4) 0.6006(2) 0.95107(19) 0.0427(6) Uani 1 1 d . . .
H10 H 0.5747 0.5501 0.9283 0.064 Uiso 1 1 calc R . .
H10A H 0.7592 0.6180 1.0239 0.064 Uiso 1 1 calc R . .
H10B H 0.7974 0.5383 0.9266 0.064 Uiso 1 1 calc R . .
C11 C 0.7080(3) 0.8894(2) 1.06078(18) 0.0324(5) Uani 1 1 d . . .
C12 C 0.6930(3) 0.8990(3) 1.14370(18) 0.0349(5) Uani 1 1 d . . .
C13 C 0.6878(3) 0.9149(3) 1.24548(17) 0.0316(5) Uani 1 1 d . . .
C14 C 0.6742(4) 0.7919(3) 1.2959(2) 0.0429(6) Uani 1 1 d . . .
H14 H 0.6624 0.6960 1.2617 0.052 Uiso 1 1 calc R . .
C15 C 0.6775(5) 0.8080(3) 1.3944(2) 0.0557(8) Uani 1 1 d . . .
H15 H 0.6681 0.7234 1.4281 0.067 Uiso 1 1 calc R . .
C16 C 0.6947(5) 0.9476(4) 1.4452(2) 0.0584(8) Uani 1 1 d . . .
H16 H 0.6980 0.9587 1.5136 0.070 Uiso 1 1 calc R . .
C17 C 0.7069(4) 1.0698(3) 1.3957(2) 0.0503(7) Uani 1 1 d . . .
H17 H 0.7179 1.1652 1.4303 0.060 Uiso 1 1 calc R . .
C18 C 0.7033(4) 1.0549(3) 1.29676(19) 0.0381(5) Uani 1 1 d . . .
H18 H 0.7114 1.1398 1.2633 0.046 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 C2 1.832(3) . ?
Rh1 C1 1.914(3) . ?
Rh1 C3 2.052(2) . ?
Rh1 Cl1 2.3600(8) . ?
O1 C1 1.125(3) . ?
O2 C2 1.122(4) . ?
N1 C3 1.343(3) . ?
N1 C4 1.398(3) . ?
N1 C10 1.460(3) . ?
N2 C3 1.376(2) . ?
N2 C9 1.383(3) . ?
N2 C5 1.391(3) . ?
C4 C5 1.375(3) . ?
C4 C11 1.410(3) . ?
C5 C6 1.420(3) . ?
C6 C7 1.347(3) . ?
C7 C8 1.420(3) . ?
C8 C9 1.342(3) . ?
C11 C12 1.190(3) . ?
C12 C13 1.432(3) . ?
C13 C14 1.392(3) . ?
C13 C18 1.397(3) . ?
C14 C15 1.369(4) . ?
C15 C16 1.388(4) . ?
C16 C17 1.377(4) . ?
C17 C18 1.376(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
C2 Rh1 C1 93.03(11) . . ?
C2 Rh1 C3 89.47(10) . . ?
C1 Rh1 C3 176.27(9) . . ?
C2 Rh1 Cl1 177.30(9) . . ?
C1 Rh1 Cl1 88.15(8) . . ?
C3 Rh1 Cl1 89.47(6) . . ?
C3 N1 C4 112.65(17) . . ?
C3 N1 C10 123.93(19) . . ?
C4 N1 C10 123.42(19) . . ?
C3 N2 C9 126.92(18) . . ?
C3 N2 C5 111.52(17) . . ?
C9 N2 C5 121.56(17) . . ?
O1 C1 Rh1 178.6(2) . . ?
O2 C2 Rh1 178.2(3) . . ?
N1 C3 N2 103.89(18) . . ?
N1 C3 Rh1 129.59(15) . . ?
N2 C3 Rh1 126.27(15) . . ?
C5 C4 N1 105.68(18) . . ?
C5 C4 C11 130.6(2) . . ?
N1 C4 C11 123.65(19) . . ?
C4 C5 N2 106.22(17) . . ?
C4 C5 C6 134.7(2) . . ?
N2 C5 C6 119.05(19) . . ?
C7 C6 C5 118.5(2) . . ?
C6 C7 C8 121.0(2) . . ?
C9 C8 C7 121.0(2) . . ?
C8 C9 N2 118.8(2) . . ?
C12 C11 C4 177.1(2) . . ?
C11 C12 C13 176.5(2) . . ?
C14 C13 C18 118.9(2) . . ?
C14 C13 C12 120.5(2) . . ?
C18 C13 C12 120.5(2) . . ?
C15 C14 C13 120.5(2) . . ?
C14 C15 C16 120.3(3) . . ?
C17 C16 C15 119.6(3) . . ?
C18 C17 C16 120.6(2) . . ?
C17 C18 C13 120.0(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
C2 Rh1 C1 O1 137(9) . . . . ?
C3 Rh1 C1 O1 5(10) . . . . ?
Cl1 Rh1 C1 O1 -46(9) . . . . ?
C1 Rh1 C2 O2 110(8) . . . . ?
C3 Rh1 C2 O2 -73(8) . . . . ?
Cl1 Rh1 C2 O2 -5(9) . . . . ?
C4 N1 C3 N2 -1.4(2) . . . . ?
C10 N1 C3 N2 178.68(19) . . . . ?
C4 N1 C3 Rh1 173.20(15) . . . . ?
C10 N1 C3 Rh1 -6.8(3) . . . . ?
C9 N2 C3 N1 -178.21(19) . . . . ?
C5 N2 C3 N1 1.8(2) . . . . ?
C9 N2 C3 Rh1 7.0(3) . . . . ?
C5 N2 C3 Rh1 -172.99(14) . . . . ?
C2 Rh1 C3 N1 109.2(2) . . . . ?
C1 Rh1 C3 N1 -118.7(13) . . . . ?
Cl1 Rh1 C3 N1 -68.30(19) . . . . ?
C2 Rh1 C3 N2 -77.3(2) . . . . ?
C1 Rh1 C3 N2 54.8(14) . . . . ?
Cl1 Rh1 C3 N2 105.15(18) . . . . ?
C3 N1 C4 C5 0.4(2) . . . . ?
C10 N1 C4 C5 -179.6(2) . . . . ?
C3 N1 C4 C11 -176.3(2) . . . . ?
C10 N1 C4 C11 3.6(3) . . . . ?
N1 C4 C5 N2 0.7(2) . . . . ?
C11 C4 C5 N2 177.1(2) . . . . ?
N1 C4 C5 C6 -177.1(2) . . . . ?
C11 C4 C5 C6 -0.6(4) . . . . ?
C3 N2 C5 C4 -1.6(2) . . . . ?
C9 N2 C5 C4 178.42(18) . . . . ?
C3 N2 C5 C6 176.60(19) . . . . ?
C9 N2 C5 C6 -3.4(3) . . . . ?
C4 C5 C6 C7 180.0(2) . . . . ?
N2 C5 C6 C7 2.4(3) . . . . ?
C5 C6 C7 C8 0.4(3) . . . . ?
C6 C7 C8 C9 -2.5(4) . . . . ?
C7 C8 C9 N2 1.6(3) . . . . ?
C3 N2 C9 C8 -178.7(2) . . . . ?
C5 N2 C9 C8 1.3(3) . . . . ?
C5 C4 C11 C12 -112(5) . . . . ?
N1 C4 C11 C12 64(5) . . . . ?
C4 C11 C12 C13 41(8) . . . . ?
C11 C12 C13 C14 -108(4) . . . . ?
C11 C12 C13 C18 70(4) . . . . ?
C18 C13 C14 C15 -0.5(4) . . . . ?
C12 C13 C14 C15 177.3(2) . . . . ?
C13 C14 C15 C16 0.0(4) . . . . ?
C14 C15 C16 C17 0.5(5) . . . . ?
C15 C16 C17 C18 -0.4(5) . . . . ?
C16 C17 C18 C13 -0.2(4) . . . . ?
C14 C13 C18 C17 0.6(4) . . . . ?
C12 C13 C18 C17 -177.2(2) . . . . ?

_diffrn_measured_fraction_theta_max 0.982
_diffrn_reflns_theta_full        27.50
_diffrn_measured_fraction_theta_full 0.982
_refine_diff_density_max         0.503
_refine_diff_density_min         -0.933
_refine_diff_density_rms         0.071
