# Electronic Supplementary Material (ESI) for Chemical Science
# This journal is © The Royal Society of Chemistry 2013


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#                                CCDC 
# 
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#  This CIF contains data from an original supplementary publication 
#  deposited with the CCDC, and may include chemical, crystal,   
#  experimental, refinement, atomic coordinates, 
#  anisotropic displacement parameters and molecular geometry data,
#  as required by the journal to which it was submitted. 
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data_120618_s4_qxr
_database_code_depnum_ccdc_archive 'CCDC 904158'
#TrackingRef '14405_web_deposit_cif_file_0_XurongQin_1349257764.3a.cif'
_audit_creation_date             2012-06-18
_audit_creation_method           
;
Olex2 1.1
(compiled 2011.11.01 svn.r2039, GUI svn.r3906)
;
_chemical_name_common            ?
_chemical_name_systematic        
;
?
;
_chemical_formula_moiety         'C20 H13 N3 S'
_chemical_formula_sum            'C20 H13 N3 S'
_chemical_formula_weight         327.39
_chemical_melting_point          ?
_chemical_oxdiff_formula         C12H15N3S1
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'
S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'
loop_
_space_group_symop_id
_space_group_symop_operation_xyz
1 'x, y, z'
2 '-x, -y, -z'
_cell_length_a                   8.3008(6)
_cell_length_b                   10.0109(8)
_cell_length_c                   10.1613(6)
_cell_angle_alpha                76.211(6)
_cell_angle_beta                 79.041(6)
_cell_angle_gamma                87.821(6)
_cell_volume                     805.07(10)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    1962
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      28.9300
_cell_measurement_theta_min      2.9442
_exptl_absorpt_coefficient_mu    0.206
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.99190
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.21 (release 20-01-2012 CrysAlis171 .NET)
(compiled Jan 23 2012,18:06:46)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.351
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             340
_exptl_crystal_size_max          0.35
_exptl_crystal_size_mid          0.30
_exptl_crystal_size_min          0.25
_exptl_special_details           
;
?
;
_diffrn_reflns_av_R_equivalents  0.0238
_diffrn_reflns_av_unetI/netI     0.0490
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            6779
_diffrn_reflns_theta_full        26.37
_diffrn_reflns_theta_max         26.37
_diffrn_reflns_theta_min         2.95
_diffrn_ambient_temperature      293.15
_diffrn_detector_area_resol_mean 16.0874
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_details      
;
#__ type_ start__ end____ width___ exp.time_
1 omega -25.00 1.00 1.0000 4.0000
omega____ theta____ kappa____ phi______ frames
- -16.8924 -99.0000 -30.0000 26
#__ type_ start__ end____ width___ exp.time_
2 omega -21.00 22.00 1.0000 4.0000
omega____ theta____ kappa____ phi______ frames
- -16.8924 -99.0000 30.0000 43
#__ type_ start__ end____ width___ exp.time_
3 omega -14.00 15.00 1.0000 4.0000
omega____ theta____ kappa____ phi______ frames
- -16.8924 -99.0000 -180.0000 29
#__ type_ start__ end____ width___ exp.time_
4 omega -90.00 -45.00 1.0000 4.0000
omega____ theta____ kappa____ phi______ frames
- -16.8924 -178.0000 -180.0000 45
#__ type_ start__ end____ width___ exp.time_
5 omega -5.00 83.00 1.0000 4.0000
omega____ theta____ kappa____ phi______ frames
- 19.8611 37.0000 -120.0000 88
#__ type_ start__ end____ width___ exp.time_
6 omega 38.00 82.00 1.0000 4.0000
omega____ theta____ kappa____ phi______ frames
- 19.8611 178.0000 90.0000 44
#__ type_ start__ end____ width___ exp.time_
7 omega -53.00 46.00 1.0000 4.0000
omega____ theta____ kappa____ phi______ frames
- 19.8611 -37.0000 60.0000 99
#__ type_ start__ end____ width___ exp.time_
8 omega -49.00 6.00 1.0000 4.0000
omega____ theta____ kappa____ phi______ frames
- 19.8611 -57.0000 -180.0000 55
;
_diffrn_measurement_device_type  'Xcalibur, Eos'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_UB_11      0.0767354000
_diffrn_orient_matrix_UB_12      0.0340801000
_diffrn_orient_matrix_UB_13      -0.0126743000
_diffrn_orient_matrix_UB_21      0.0410771000
_diffrn_orient_matrix_UB_22      -0.0623405000
_diffrn_orient_matrix_UB_23      -0.0058627000
_diffrn_orient_matrix_UB_31      -0.0003555000
_diffrn_orient_matrix_UB_32      0.0165843000
_diffrn_orient_matrix_UB_33      -0.0718150000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.7107
_diffrn_source                   'Enhance (Mo) X-ray Source'
_diffrn_source_current           n/a
_diffrn_source_voltage           n/a
_diffrn_standards_decay_%        ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_number         ?
_reflns_number_gt                2225
_reflns_number_total             3297
_reflns_odcompleteness_completeness 99.88
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     26.32
_reflns_threshold_expression     >2sigma(I)
_computing_cell_refinement       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.21 (release 20-01-2012 CrysAlis171 .NET)
(compiled Jan 23 2012,18:06:46)
;
_computing_data_collection       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.21 (release 20-01-2012 CrysAlis171 .NET)
(compiled Jan 23 2012,18:06:46)
;
_computing_data_reduction        
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.21 (release 20-01-2012 CrysAlis171 .NET)
(compiled Jan 23 2012,18:06:46)
;
_computing_molecular_graphics    
;
O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann,
OLEX2: a complete structure solution, refinement and analysis program.
J. Appl. Cryst. (2009). 42, 339-341.
;
_computing_publication_material  
;
O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann,
OLEX2: a complete structure solution, refinement and analysis program.
J. Appl. Cryst. (2009). 42, 339-341.
;
_computing_structure_refinement  
;
SHELXL, G.M. Sheldrick, Acta Cryst.
2008). A64, 112-122
;
_computing_structure_solution    
;
SHELXS, G.M. Sheldrick, Acta Cryst.
(2008). A64, 112-122
;
_refine_diff_density_max         0.162
_refine_diff_density_min         -0.238
_refine_diff_density_rms         0.041
_refine_ls_extinction_coef       ?
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.034
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     217
_refine_ls_number_reflns         3297
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0814
_refine_ls_R_factor_gt           0.0495
_refine_ls_restrained_S_all      1.034
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'calc w=1/[\s^2^(Fo^2^)+(0.0405P)^2^+0.2036P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1013
_refine_ls_wR_factor_ref         0.1215
_refine_special_details          
;
Refinement of F^2^ against ALL reflections. The weighted R-factor wR and
goodness of fit S are based on F^2^, conventional R-factors R are based
on F, with F set to zero for negative F^2^. The threshold expression of
F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is
not relevant to the choice of reflections for refinement. R-factors based
on F^2^ are statistically about twice as large as those based on F, and R-
factors based on ALL data will be even larger.
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
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
S1 S 0.03156(8) 0.30412(7) 0.89192(6) 0.0565(2) Uani 1 1 d . . .
N1 N -0.1581(2) 0.09987(19) 0.66589(17) 0.0432(5) Uani 1 1 d . . .
N2 N -0.1124(2) 0.1150(2) 0.43009(19) 0.0495(5) Uani 1 1 d . . .
N3 N -0.0681(2) 0.3092(2) 0.51688(19) 0.0530(5) Uani 1 1 d . . .
C1 C 0.0397(3) 0.1985(2) 0.7780(2) 0.0463(6) Uani 1 1 d . . .
C2 C 0.1899(3) 0.2002(3) 0.6973(3) 0.0581(7) Uani 1 1 d . . .
H2 H 0.2159 0.1488 0.6311 0.070 Uiso 1 1 calc R . .
C3 C 0.3045(3) 0.2889(3) 0.7239(3) 0.0552(6) Uani 1 1 d . . .
C4 C 0.2345(3) 0.3540(2) 0.8284(2) 0.0518(6) Uani 1 1 d . . .
C5 C 0.3249(4) 0.4447(3) 0.8710(3) 0.0681(8) Uani 1 1 d . . .
H5 H 0.2772 0.4873 0.9406 0.082 Uiso 1 1 calc R . .
C6 C 0.4862(4) 0.4698(3) 0.8078(3) 0.0784(9) Uani 1 1 d . . .
H6 H 0.5480 0.5307 0.8345 0.094 Uiso 1 1 calc R . .
C7 C 0.5571(4) 0.4058(3) 0.7055(4) 0.0848(10) Uani 1 1 d . . .
H7 H 0.6668 0.4233 0.6649 0.102 Uiso 1 1 calc R . .
C8 C 0.4693(4) 0.3167(3) 0.6622(3) 0.0769(9) Uani 1 1 d . . .
H8 H 0.5188 0.2749 0.5923 0.092 Uiso 1 1 calc R . .
C9 C -0.1048(3) 0.1183(2) 0.7844(2) 0.0452(6) Uani 1 1 d . . .
C10 C -0.1963(3) 0.0366(2) 0.8972(2) 0.0501(6) Uani 1 1 d . . .
H10 H -0.1855 0.0297 0.9880 0.060 Uiso 1 1 calc R . .
C11 C -0.3114(3) -0.0370(2) 0.8541(2) 0.0480(6) Uani 1 1 d . . .
C12 C -0.2849(3) 0.0018(2) 0.7097(2) 0.0441(5) Uani 1 1 d . . .
C13 C -0.3795(3) -0.0510(3) 0.6348(3) 0.0543(6) Uani 1 1 d . . .
H13 H -0.3620 -0.0242 0.5390 0.065 Uiso 1 1 calc R . .
C14 C -0.5007(3) -0.1447(3) 0.7082(3) 0.0646(7) Uani 1 1 d . . .
H14 H -0.5652 -0.1824 0.6606 0.078 Uiso 1 1 calc R . .
C15 C -0.5292(3) -0.1846(3) 0.8517(3) 0.0627(7) Uani 1 1 d . . .
H15 H -0.6125 -0.2475 0.8979 0.075 Uiso 1 1 calc R . .
C16 C -0.4360(3) -0.1322(3) 0.9255(3) 0.0558(6) Uani 1 1 d . . .
H16 H -0.4551 -0.1593 1.0213 0.067 Uiso 1 1 calc R . .
C17 C -0.1090(3) 0.1789(2) 0.5300(2) 0.0427(5) Uani 1 1 d . . .
C18 C -0.0146(4) 0.3795(3) 0.3878(3) 0.0659(8) Uani 1 1 d . . .
H18 H 0.0178 0.4707 0.3725 0.079 Uiso 1 1 calc R . .
C19 C -0.0054(3) 0.3222(3) 0.2763(3) 0.0653(8) Uani 1 1 d . . .
H19 H 0.0360 0.3715 0.1871 0.078 Uiso 1 1 calc R . .
C20 C -0.0600(3) 0.1897(3) 0.3026(2) 0.0563(7) Uani 1 1 d . . .
H20 H -0.0605 0.1501 0.2287 0.068 Uiso 1 1 calc R . .
loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
S1 0.0664(5) 0.0594(4) 0.0485(4) -0.0222(3) -0.0093(3) -0.0049(3)
N1 0.0480(11) 0.0460(11) 0.0377(10) -0.0103(8) -0.0121(8) -0.0018(9)
N2 0.0597(13) 0.0510(12) 0.0413(11) -0.0145(9) -0.0136(9) 0.0027(10)
N3 0.0687(14) 0.0457(12) 0.0451(12) -0.0110(9) -0.0106(10) -0.0041(10)
C1 0.0548(15) 0.0489(14) 0.0394(12) -0.0137(10) -0.0155(11) 0.0027(11)
C2 0.0582(16) 0.0682(18) 0.0586(16) -0.0311(13) -0.0166(13) 0.0010(14)
C3 0.0544(16) 0.0550(16) 0.0611(16) -0.0200(13) -0.0160(12) 0.0053(13)
C4 0.0601(16) 0.0458(14) 0.0544(15) -0.0134(12) -0.0210(12) 0.0015(12)
C5 0.076(2) 0.0602(18) 0.0783(19) -0.0290(15) -0.0233(15) -0.0022(15)
C6 0.072(2) 0.0611(19) 0.112(3) -0.0249(18) -0.0337(18) -0.0081(16)
C7 0.0551(18) 0.084(2) 0.116(3) -0.029(2) -0.0091(17) -0.0092(17)
C8 0.0586(18) 0.087(2) 0.092(2) -0.0398(18) -0.0080(15) -0.0017(16)
C9 0.0498(14) 0.0499(14) 0.0403(13) -0.0154(11) -0.0134(10) 0.0034(11)
C10 0.0605(15) 0.0538(15) 0.0379(13) -0.0131(11) -0.0113(11) 0.0032(12)
C11 0.0528(14) 0.0458(14) 0.0443(13) -0.0106(11) -0.0070(11) 0.0045(12)
C12 0.0464(13) 0.0411(13) 0.0466(13) -0.0126(10) -0.0112(10) 0.0039(11)
C13 0.0570(15) 0.0563(16) 0.0527(15) -0.0136(12) -0.0163(12) -0.0026(13)
C14 0.0641(18) 0.0602(17) 0.0743(19) -0.0187(14) -0.0194(14) -0.0094(14)
C15 0.0602(17) 0.0514(16) 0.0717(19) -0.0115(14) -0.0019(13) -0.0103(13)
C16 0.0642(17) 0.0461(15) 0.0513(15) -0.0055(12) -0.0040(12) 0.0016(13)
C17 0.0413(13) 0.0471(14) 0.0413(13) -0.0112(11) -0.0116(10) 0.0043(11)
C18 0.092(2) 0.0493(16) 0.0526(16) -0.0044(13) -0.0119(14) -0.0106(15)
C19 0.088(2) 0.0616(18) 0.0404(14) -0.0047(13) -0.0065(13) -0.0061(15)
C20 0.0686(17) 0.0605(17) 0.0426(14) -0.0164(12) -0.0130(12) 0.0062(14)
_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
S1 C1 1.735(2) . ?
S1 C4 1.733(3) . ?
N1 C9 1.412(3) . ?
N1 C12 1.401(3) . ?
N1 C17 1.410(3) . ?
N2 C17 1.328(3) . ?
N2 C20 1.332(3) . ?
N3 C17 1.330(3) . ?
N3 C18 1.332(3) . ?
C1 C2 1.354(3) . ?
C1 C9 1.452(3) . ?
C2 H2 0.9300 . ?
C2 C3 1.429(3) . ?
C3 C4 1.399(3) . ?
C3 C8 1.400(3) . ?
C4 C5 1.391(3) . ?
C5 H5 0.9300 . ?
C5 C6 1.374(4) . ?
C6 H6 0.9300 . ?
C6 C7 1.377(4) . ?
C7 H7 0.9300 . ?
C7 C8 1.371(4) . ?
C8 H8 0.9300 . ?
C9 C10 1.352(3) . ?
C10 H10 0.9300 . ?
C10 C11 1.419(3) . ?
C11 C12 1.402(3) . ?
C11 C16 1.402(3) . ?
C12 C13 1.388(3) . ?
C13 H13 0.9300 . ?
C13 C14 1.379(3) . ?
C14 H14 0.9300 . ?
C14 C15 1.393(3) . ?
C15 H15 0.9300 . ?
C15 C16 1.369(4) . ?
C16 H16 0.9300 . ?
C18 H18 0.9300 . ?
C18 C19 1.375(4) . ?
C19 H19 0.9300 . ?
C19 C20 1.367(3) . ?
C20 H20 0.9300 . ?
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
C4 S1 C1 91.66(12) . . ?
C12 N1 C9 107.67(18) . . ?
C12 N1 C17 125.58(18) . . ?
C17 N1 C9 126.23(19) . . ?
C17 N2 C20 115.2(2) . . ?
C17 N3 C18 115.0(2) . . ?
C2 C1 S1 112.10(18) . . ?
C2 C1 C9 129.2(2) . . ?
C9 C1 S1 118.68(17) . . ?
C1 C2 H2 123.4 . . ?
C1 C2 C3 113.3(2) . . ?
C3 C2 H2 123.4 . . ?
C4 C3 C2 111.9(2) . . ?
C4 C3 C8 118.4(3) . . ?
C8 C3 C2 129.6(3) . . ?
C3 C4 S1 111.03(19) . . ?
C5 C4 S1 127.5(2) . . ?
C5 C4 C3 121.4(3) . . ?
C4 C5 H5 120.7 . . ?
C6 C5 C4 118.6(3) . . ?
C6 C5 H5 120.7 . . ?
C5 C6 H6 119.6 . . ?
C5 C6 C7 120.7(3) . . ?
C7 C6 H6 119.6 . . ?
C6 C7 H7 119.4 . . ?
C8 C7 C6 121.3(3) . . ?
C8 C7 H7 119.4 . . ?
C3 C8 H8 120.2 . . ?
C7 C8 C3 119.6(3) . . ?
C7 C8 H8 120.2 . . ?
N1 C9 C1 123.09(19) . . ?
C10 C9 N1 108.7(2) . . ?
C10 C9 C1 127.7(2) . . ?
C9 C10 H10 125.6 . . ?
C9 C10 C11 108.7(2) . . ?
C11 C10 H10 125.6 . . ?
C12 C11 C10 107.3(2) . . ?
C16 C11 C10 133.2(2) . . ?
C16 C11 C12 119.5(2) . . ?
N1 C12 C11 107.57(19) . . ?
C13 C12 N1 130.6(2) . . ?
C13 C12 C11 121.8(2) . . ?
C12 C13 H13 121.4 . . ?
C14 C13 C12 117.3(2) . . ?
C14 C13 H13 121.4 . . ?
C13 C14 H14 119.1 . . ?
C13 C14 C15 121.9(2) . . ?
C15 C14 H14 119.1 . . ?
C14 C15 H15 119.6 . . ?
C16 C15 C14 120.8(2) . . ?
C16 C15 H15 119.6 . . ?
C11 C16 H16 120.6 . . ?
C15 C16 C11 118.8(2) . . ?
C15 C16 H16 120.6 . . ?
N2 C17 N1 116.0(2) . . ?
N2 C17 N3 127.6(2) . . ?
N3 C17 N1 116.32(19) . . ?
N3 C18 H18 118.8 . . ?
N3 C18 C19 122.5(2) . . ?
C19 C18 H18 118.8 . . ?
C18 C19 H19 121.5 . . ?
C20 C19 C18 117.0(2) . . ?
C20 C19 H19 121.5 . . ?
N2 C20 C19 122.5(2) . . ?
N2 C20 H20 118.7 . . ?
C19 C20 H20 118.7 . . ?


data_121112_s1_qxr
_database_code_depnum_ccdc_archive 'CCDC 910498'
#TrackingRef 'web_deposit_cif_file_0_XurongQin_1352709253.121112_s1_qxr.cif'
_audit_creation_date             2012-11-12
_audit_creation_method           
;
Olex2 1.1
(compiled 2011.11.01 svn.r2039, GUI svn.r3906)
;
_chemical_name_common            ?
_chemical_name_systematic        
;
?
;
_chemical_formula_moiety         'C22 H23 Cl N3 Rh'
_chemical_formula_sum            'C22 H23 Cl N3 Rh'
_chemical_formula_weight         467.79
_chemical_absolute_configuration ad
_chemical_melting_point          ?
_chemical_oxdiff_formula         C12H10N2Rh1Cl2
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'
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'
_space_group_crystal_system      tetragonal
_space_group_IT_number           114
_space_group_name_H-M_alt        'P -4 21 c'
_space_group_name_Hall           'P -4 2n'
loop_
_space_group_symop_id
_space_group_symop_operation_xyz
1 'x, y, z'
2 'y, -x, -z'
3 '-x, -y, z'
4 '-y, x, -z'
5 'x+1/2, -y+1/2, -z+1/2'
6 '-x+1/2, y+1/2, -z+1/2'
7 '-y+1/2, -x+1/2, z+1/2'
8 'y+1/2, x+1/2, z+1/2'
_cell_length_a                   22.2937(4)
_cell_length_b                   22.2937(4)
_cell_length_c                   8.7660(2)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_volume                     4356.80(16)
_cell_formula_units_Z            8
_cell_measurement_reflns_used    2880
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      29.1042
_cell_measurement_theta_min      2.8835
_exptl_absorpt_coefficient_mu    0.917
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.84310
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.21 (release 20-01-2012 CrysAlis171 .NET)
(compiled Jan 23 2012,18:06:46)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            red
_exptl_crystal_density_diffrn    1.426
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             1904
_exptl_crystal_size_max          0.30
_exptl_crystal_size_mid          0.25
_exptl_crystal_size_min          0.20
_exptl_special_details           
;
?
;
_diffrn_reflns_av_R_equivalents  0.0244
_diffrn_reflns_av_unetI/netI     0.0372
_diffrn_reflns_limit_h_max       24
_diffrn_reflns_limit_h_min       -22
_diffrn_reflns_limit_k_max       26
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       6
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_number            9519
_diffrn_reflns_theta_full        25.00
_diffrn_reflns_theta_max         25.00
_diffrn_reflns_theta_min         2.89
_diffrn_ambient_temperature      293.15
_diffrn_detector_area_resol_mean 16.0874
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_details      
;
#__ type_ start__ end____ width___ exp.time_
1 omega -3.00 91.50 0.7000 10.0000
omega____ theta____ kappa____ phi______ frames
- 19.8611 37.0000 30.0000 135
#__ type_ start__ end____ width___ exp.time_
2 omega -10.00 21.50 0.7000 10.0000
omega____ theta____ kappa____ phi______ frames
- 19.8611 77.0000 120.0000 45
;
_diffrn_measurement_device_type  'Xcalibur, Eos'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_UB_11      -0.0037062000
_diffrn_orient_matrix_UB_12      -0.0315053000
_diffrn_orient_matrix_UB_13      0.0056997000
_diffrn_orient_matrix_UB_21      0.0315912000
_diffrn_orient_matrix_UB_22      -0.0037983000
_diffrn_orient_matrix_UB_23      -0.0020288000
_diffrn_orient_matrix_UB_31      0.0010301000
_diffrn_orient_matrix_UB_32      0.0021256000
_diffrn_orient_matrix_UB_33      0.0806962000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.7107
_diffrn_source                   'Enhance (Mo) X-ray Source'
_diffrn_source_current           n/a
_diffrn_source_voltage           n/a
_diffrn_standards_decay_%        ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_number         ?
_reflns_number_gt                3291
_reflns_number_total             3822
_reflns_odcompleteness_completeness 99.65
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     26.32
_reflns_threshold_expression     >2sigma(I)
_computing_cell_refinement       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.21 (release 20-01-2012 CrysAlis171 .NET)
(compiled Jan 23 2012,18:06:46)
;
_computing_data_collection       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.21 (release 20-01-2012 CrysAlis171 .NET)
(compiled Jan 23 2012,18:06:46)
;
_computing_data_reduction        
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.21 (release 20-01-2012 CrysAlis171 .NET)
(compiled Jan 23 2012,18:06:46)
;
_computing_molecular_graphics    
;
O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann,
OLEX2: a complete structure solution, refinement and analysis program.
J. Appl. Cryst. (2009). 42, 339-341.
;
_computing_publication_material  
;
O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann,
OLEX2: a complete structure solution, refinement and analysis program.
J. Appl. Cryst. (2009). 42, 339-341.
;
_computing_structure_refinement  
;
SHELXL, G.M. Sheldrick, Acta Cryst.
2008). A64, 112-122
;
_computing_structure_solution    
;
SHELXS, G.M. Sheldrick, Acta Cryst.
(2008). A64, 112-122
;
_refine_diff_density_max         0.264
_refine_diff_density_min         -0.383
_refine_diff_density_rms         0.054
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   -0.02(4)
_refine_ls_extinction_coef       ?
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.069
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     249
_refine_ls_number_reflns         3822
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0396
_refine_ls_R_factor_gt           0.0319
_refine_ls_restrained_S_all      1.069
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'calc w=1/[\s^2^(Fo^2^)+(0.0378P)^2^+0.1826P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0748
_refine_ls_wR_factor_ref         0.0788
_refine_special_details          
;
Refinement of F^2^ against ALL reflections. The weighted R-factor wR and
goodness of fit S are based on F^2^, conventional R-factors R are based
on F, with F set to zero for negative F^2^. The threshold expression of
F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is
not relevant to the choice of reflections for refinement. R-factors based
on F^2^ are statistically about twice as large as those based on F, and R-
factors based on ALL data will be even larger.
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
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 -0.258142(16) 0.007032(14) -0.06046(3) 0.03908(11) Uani 1 1 d . . .
Cl1 Cl -0.31863(6) -0.01561(6) -0.28136(12) 0.0553(3) Uani 1 1 d . . .
N1 N -0.21634(16) 0.11825(15) -0.1897(4) 0.0402(8) Uani 1 1 d . . .
N2 N -0.29808(14) 0.09274(16) -0.0486(4) 0.0453(8) Uani 1 1 d . . .
N3 N -0.28162(19) 0.19500(17) -0.1181(4) 0.0572(11) Uani 1 1 d . . .
C1 C -0.20210(19) 0.05662(19) -0.1911(5) 0.0384(10) Uani 1 1 d . . .
C2 C -0.1552(2) 0.0500(2) -0.2880(5) 0.0463(11) Uani 1 1 d . . .
H2 H -0.1368 0.0138 -0.3118 0.056 Uiso 1 1 calc R . .
C3 C -0.1382(2) 0.1074(2) -0.3481(5) 0.0471(11) Uani 1 1 d . . .
C4 C -0.1766(2) 0.15023(19) -0.2861(5) 0.0435(10) Uani 1 1 d . . .
C5 C -0.1721(2) 0.2104(2) -0.3241(6) 0.0616(14) Uani 1 1 d . . .
H5 H -0.1976 0.2389 -0.2814 0.074 Uiso 1 1 calc R . .
C6 C -0.1288(3) 0.2264(2) -0.4267(6) 0.0664(14) Uani 1 1 d . . .
H6 H -0.1254 0.2665 -0.4549 0.080 Uiso 1 1 calc R . .
C7 C -0.0909(3) 0.1862(3) -0.4885(6) 0.0699(16) Uani 1 1 d . . .
H7 H -0.0617 0.1991 -0.5567 0.084 Uiso 1 1 calc R . .
C8 C -0.0947(2) 0.1259(2) -0.4522(5) 0.0604(13) Uani 1 1 d . . .
H8 H -0.0687 0.0982 -0.4964 0.072 Uiso 1 1 calc R . .
C9 C -0.2669(2) 0.1371(2) -0.1160(4) 0.0434(10) Uani 1 1 d . . .
C10 C -0.3320(2) 0.2078(2) -0.0469(6) 0.0671(14) Uani 1 1 d . . .
H10 H -0.3439 0.2477 -0.0431 0.080 Uiso 1 1 calc R . .
C11 C -0.3682(2) 0.1661(3) 0.0219(6) 0.0720(17) Uani 1 1 d . . .
H11 H -0.4040 0.1769 0.0690 0.086 Uiso 1 1 calc R . .
C12 C -0.3490(2) 0.1076(3) 0.0179(6) 0.0600(14) Uani 1 1 d . . .
H12 H -0.3723 0.0779 0.0629 0.072 Uiso 1 1 calc R . .
C13 C -0.2179(3) -0.0059(3) 0.1578(5) 0.0605(13) Uani 1 1 d . . .
C14 C -0.1892(2) -0.0442(2) 0.0530(6) 0.0594(13) Uani 1 1 d . . .
C15 C -0.2335(3) -0.0840(2) -0.0063(5) 0.0584(14) Uani 1 1 d . . .
C16 C -0.2877(2) -0.0724(2) 0.0741(5) 0.0564(12) Uani 1 1 d . . .
C17 C -0.2769(3) -0.0259(2) 0.1748(5) 0.0609(14) Uani 1 1 d . . .
C18 C -0.1903(3) 0.0426(3) 0.2544(7) 0.105(3) Uani 1 1 d . . .
H18A H -0.1503 0.0505 0.2197 0.158 Uiso 1 1 calc R . .
H18B H -0.1893 0.0298 0.3589 0.158 Uiso 1 1 calc R . .
H18C H -0.2139 0.0785 0.2462 0.158 Uiso 1 1 calc R . .
C19 C -0.1233(3) -0.0454(3) 0.0128(8) 0.115(3) Uani 1 1 d . . .
H19A H -0.1186 -0.0556 -0.0929 0.172 Uiso 1 1 calc R . .
H19B H -0.1032 -0.0747 0.0746 0.172 Uiso 1 1 calc R . .
H19C H -0.1061 -0.0065 0.0312 0.172 Uiso 1 1 calc R . .
C20 C -0.2252(4) -0.1344(3) -0.1164(6) 0.111(3) Uani 1 1 d . . .
H20A H -0.2588 -0.1359 -0.1848 0.166 Uiso 1 1 calc R . .
H20B H -0.2224 -0.1715 -0.0615 0.166 Uiso 1 1 calc R . .
H20C H -0.1890 -0.1281 -0.1737 0.166 Uiso 1 1 calc R . .
C21 C -0.3463(3) -0.1064(3) 0.0498(9) 0.104(2) Uani 1 1 d . . .
H21A H -0.3766 -0.0904 0.1162 0.157 Uiso 1 1 calc R . .
H21B H -0.3403 -0.1481 0.0724 0.157 Uiso 1 1 calc R . .
H21C H -0.3589 -0.1021 -0.0543 0.157 Uiso 1 1 calc R . .
C22 C -0.3229(3) -0.0008(4) 0.2869(5) 0.101(2) Uani 1 1 d . . .
H22A H -0.3177 0.0418 0.2955 0.151 Uiso 1 1 calc R . .
H22B H -0.3172 -0.0190 0.3851 0.151 Uiso 1 1 calc R . .
H22C H -0.3626 -0.0094 0.2507 0.151 Uiso 1 1 calc R . .
loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
Rh1 0.0446(2) 0.0386(2) 0.03409(15) 0.00153(17) 0.00178(16) -0.00258(15)
Cl1 0.0648(8) 0.0588(8) 0.0424(5) -0.0012(5) -0.0102(6) -0.0070(6)
N1 0.045(2) 0.035(2) 0.0405(19) 0.0026(17) -0.0048(17) 0.0022(16)
N2 0.040(2) 0.057(2) 0.0386(17) -0.008(2) -0.0022(18) 0.0085(16)
N3 0.064(3) 0.047(2) 0.060(2) -0.0136(19) -0.012(2) 0.016(2)
C1 0.044(3) 0.035(2) 0.037(2) 0.0047(19) -0.005(2) -0.0008(18)
C2 0.054(3) 0.040(3) 0.045(2) -0.001(2) 0.008(2) 0.001(2)
C3 0.056(3) 0.047(3) 0.038(2) 0.003(2) -0.005(2) -0.006(2)
C4 0.049(3) 0.043(3) 0.039(2) 0.004(2) -0.015(2) -0.007(2)
C5 0.072(4) 0.040(3) 0.073(3) 0.004(3) -0.023(3) -0.002(2)
C6 0.082(4) 0.055(3) 0.062(3) 0.030(3) -0.019(3) -0.020(3)
C7 0.070(4) 0.084(4) 0.056(3) 0.025(3) -0.001(3) -0.028(3)
C8 0.061(3) 0.067(3) 0.053(3) 0.002(3) 0.012(3) -0.012(2)
C9 0.052(3) 0.041(3) 0.037(2) -0.0052(19) -0.009(2) 0.002(2)
C10 0.070(4) 0.066(3) 0.065(3) -0.026(3) -0.013(3) 0.026(3)
C11 0.055(3) 0.106(5) 0.056(3) -0.030(3) -0.012(3) 0.035(3)
C12 0.049(3) 0.079(4) 0.052(3) -0.007(3) 0.002(2) 0.006(3)
C13 0.078(4) 0.059(3) 0.045(2) 0.010(3) -0.022(3) -0.014(3)
C14 0.063(3) 0.059(3) 0.056(3) 0.028(3) -0.001(3) 0.010(2)
C15 0.101(4) 0.033(2) 0.040(2) 0.012(2) 0.008(3) 0.015(3)
C16 0.079(4) 0.044(3) 0.046(2) 0.012(2) 0.006(3) -0.018(2)
C17 0.086(4) 0.064(4) 0.032(2) 0.006(2) 0.007(3) 0.007(3)
C18 0.168(7) 0.062(4) 0.086(4) 0.007(3) -0.063(5) -0.030(4)
C19 0.063(4) 0.146(6) 0.135(6) 0.089(5) -0.008(4) 0.021(4)
C20 0.216(9) 0.059(4) 0.058(3) 0.001(3) 0.026(4) 0.035(5)
C21 0.103(5) 0.117(6) 0.093(4) 0.019(5) -0.003(4) -0.058(4)
C22 0.129(6) 0.131(6) 0.043(2) 0.002(4) 0.024(3) 0.032(5)
_geom_special_details            
;
All esds (except the esd in the dihedral angle between two l.s. planes)
are estimated using the full covariance matrix. The cell esds are taken
into account individually in the estimation of esds in distances, angles
and torsion angles; correlations between esds in cell parameters are only
used when they are defined by crystal symmetry. An approximate (isotropic)
treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Rh1 Cl1 2.4130(11) . ?
Rh1 N2 2.111(3) . ?
Rh1 C1 2.024(4) . ?
Rh1 C13 2.134(4) . ?
Rh1 C14 2.159(5) . ?
Rh1 C15 2.154(4) . ?
Rh1 C16 2.228(4) . ?
Rh1 C17 2.229(4) . ?
N1 C1 1.410(5) . ?
N1 C4 1.416(5) . ?
N1 C9 1.365(5) . ?
N2 C9 1.345(5) . ?
N2 C12 1.318(6) . ?
N3 C9 1.332(5) . ?
N3 C10 1.317(6) . ?
C1 C2 1.355(6) . ?
C2 C3 1.433(6) . ?
C3 C4 1.393(6) . ?
C3 C8 1.395(6) . ?
C4 C5 1.387(6) . ?
C5 C6 1.367(7) . ?
C6 C7 1.346(7) . ?
C7 C8 1.384(7) . ?
C10 C11 1.369(8) . ?
C11 C12 1.373(7) . ?
C13 C14 1.409(7) . ?
C13 C17 1.398(7) . ?
C13 C18 1.505(7) . ?
C14 C15 1.425(7) . ?
C14 C19 1.511(7) . ?
C15 C16 1.421(7) . ?
C15 C20 1.493(7) . ?
C16 C17 1.383(6) . ?
C16 C21 1.526(7) . ?
C17 C22 1.527(7) . ?
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
N2 Rh1 Cl1 89.61(9) . . ?
N2 Rh1 C13 104.82(18) . . ?
N2 Rh1 C14 139.22(17) . . ?
N2 Rh1 C15 161.62(16) . . ?
N2 Rh1 C16 124.70(17) . . ?
N2 Rh1 C17 100.01(16) . . ?
C1 Rh1 Cl1 90.29(12) . . ?
C1 Rh1 N2 78.10(15) . . ?
C1 Rh1 C13 108.76(18) . . ?
C1 Rh1 C14 96.33(18) . . ?
C1 Rh1 C15 118.81(19) . . ?
C1 Rh1 C16 156.41(18) . . ?
C1 Rh1 C17 145.04(19) . . ?
C13 Rh1 Cl1 157.93(15) . . ?
C13 Rh1 C14 38.3(2) . . ?
C13 Rh1 C15 64.4(2) . . ?
C13 Rh1 C16 62.73(18) . . ?
C13 Rh1 C17 37.28(19) . . ?
C14 Rh1 Cl1 131.06(16) . . ?
C14 Rh1 C16 62.95(19) . . ?
C14 Rh1 C17 62.13(19) . . ?
C15 Rh1 Cl1 97.01(14) . . ?
C15 Rh1 C14 38.60(18) . . ?
C15 Rh1 C16 37.79(18) . . ?
C15 Rh1 C17 62.18(17) . . ?
C16 Rh1 Cl1 95.37(13) . . ?
C16 Rh1 C17 36.14(17) . . ?
C17 Rh1 Cl1 124.67(16) . . ?
C1 N1 C4 110.2(3) . . ?
C9 N1 C1 119.3(4) . . ?
C9 N1 C4 130.1(4) . . ?
C9 N2 Rh1 115.2(3) . . ?
C12 N2 Rh1 127.8(3) . . ?
C12 N2 C9 117.0(4) . . ?
C10 N3 C9 114.4(4) . . ?
N1 C1 Rh1 112.9(3) . . ?
C2 C1 Rh1 140.5(3) . . ?
C2 C1 N1 106.5(4) . . ?
C1 C2 C3 109.7(4) . . ?
C4 C3 C2 107.9(4) . . ?
C4 C3 C8 118.7(4) . . ?
C8 C3 C2 133.5(4) . . ?
C3 C4 N1 105.7(4) . . ?
C5 C4 N1 132.6(5) . . ?
C5 C4 C3 121.7(5) . . ?
C6 C5 C4 117.5(5) . . ?
C7 C6 C5 122.3(5) . . ?
C6 C7 C8 121.1(5) . . ?
C7 C8 C3 118.7(5) . . ?
N2 C9 N1 114.1(4) . . ?
N3 C9 N1 119.7(4) . . ?
N3 C9 N2 126.2(4) . . ?
N3 C10 C11 124.3(5) . . ?
C10 C11 C12 116.7(5) . . ?
N2 C12 C11 121.2(5) . . ?
C14 C13 Rh1 71.8(2) . . ?
C14 C13 C18 128.2(6) . . ?
C17 C13 Rh1 75.1(3) . . ?
C17 C13 C14 107.6(5) . . ?
C17 C13 C18 123.6(6) . . ?
C18 C13 Rh1 125.4(4) . . ?
C13 C14 Rh1 69.9(3) . . ?
C13 C14 C15 107.5(4) . . ?
C13 C14 C19 127.1(6) . . ?
C15 C14 Rh1 70.5(3) . . ?
C15 C14 C19 125.4(6) . . ?
C19 C14 Rh1 126.4(3) . . ?
C14 C15 Rh1 70.9(3) . . ?
C14 C15 C20 128.1(6) . . ?
C16 C15 Rh1 73.9(3) . . ?
C16 C15 C14 107.2(4) . . ?
C16 C15 C20 124.3(6) . . ?
C20 C15 Rh1 126.7(3) . . ?
C15 C16 Rh1 68.3(2) . . ?
C15 C16 C21 124.7(5) . . ?
C17 C16 Rh1 72.0(3) . . ?
C17 C16 C15 107.8(5) . . ?
C17 C16 C21 127.6(6) . . ?
C21 C16 Rh1 125.0(4) . . ?
C13 C17 Rh1 67.6(3) . . ?
C13 C17 C22 125.7(6) . . ?
C16 C17 Rh1 71.9(2) . . ?
C16 C17 C13 109.6(5) . . ?
C16 C17 C22 124.7(6) . . ?
C22 C17 Rh1 126.9(4) . . ?