# Electronic Supplementary Material (ESI) for ChemComm.
# This journal is © The Royal Society of Chemistry 2014

#######################################################################
#
#                 Cambridge Crystallographic Data Centre
#                                CCDC 
# 
#######################################################################
# 
#  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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#  fide research purposes only. It may contain copyright material
#  of the CCDC or of third parties, and may not be copied or further
#  disseminated in any form, whether machine-readable or not,
#  except for the purpose of generating routine backup copies
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#  data retrieval see:
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data_yangbm0412
_audit_creation_date             2013-10-30
_audit_creation_method           
;
Olex2 1.2
(compiled 2013.09.17 svn.r2790 for OlexSys, GUI svn.r4601)
;
_shelxl_version_number           2013-2
_chemical_name_common            ?
_chemical_name_systematic        
;
 ?
;
_chemical_formula_moiety         'C22 H24 N2 S'
_chemical_formula_sum            'C22 H24 N2 S'
_chemical_formula_weight         348.49
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 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'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      orthorhombic
_space_group_IT_number           61
_space_group_name_H-M_alt        'P b c a'
_space_group_name_Hall           '-P 2ac 2ab'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'x+1/2, -y+1/2, -z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, y, -z-1/2'
'-x-1/2, y-1/2, z'
'x, -y-1/2, z-1/2'

_cell_length_a                   14.5278(6)
_cell_length_b                   14.5993(6)
_cell_length_c                   17.0361(3)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     3613.3(2)
_cell_formula_units_Z            8
_cell_measurement_reflns_used    4324
_cell_measurement_temperature    150.00(10)
_cell_measurement_theta_max      28.3370
_cell_measurement_theta_min      3.6730
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.186
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.86405
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET)
(compiled Feb  1 2013,16:14:44)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            'clear light colourless'
_exptl_crystal_density_diffrn    1.281
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       plate
_exptl_crystal_F_000             1488
_exptl_crystal_size_max          0.3400
_exptl_crystal_size_mid          0.2700
_exptl_crystal_size_min          0.2500
_exptl_special_details           
;
 ?
;
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0326
_diffrn_reflns_av_unetI/netI     0.0381
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       18
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            10750
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_theta_full        25.500
_diffrn_reflns_theta_max         26.372
_diffrn_reflns_theta_min         3.036
_diffrn_ambient_temperature      150.00(10)
_diffrn_detector_area_resol_mean 16.0733
_diffrn_measured_fraction_theta_full 0.9966
_diffrn_measured_fraction_theta_max 0.9022
_diffrn_measurement_details      
;
#__ type_ start__ end____ width___ exp.time_
  1 omega   60.00   94.80   1.2000   10.0000
omega____ theta____ kappa____ phi______ frames
    -       22.8075   77.0000   60.0000 29

#__ type_ start__ end____ width___ exp.time_
  2 omega   15.00   95.40   1.2000   10.0000
omega____ theta____ kappa____ phi______ frames
    -       22.8075   77.0000  -60.0000 67

#__ type_ start__ end____ width___ exp.time_
  3 omega    4.00   49.60   1.2000   10.0000
omega____ theta____ kappa____ phi______ frames
    -       22.8075   77.0000  120.0000 38

#__ type_ start__ end____ width___ exp.time_
  4 omega   -8.00   18.40   1.2000   10.0000
omega____ theta____ kappa____ phi______ frames
    -       22.8075   77.0000   60.0000 22
;
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, Eos'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_UB_11      0.0248933000
_diffrn_orient_matrix_UB_12      0.0385183000
_diffrn_orient_matrix_UB_13      -0.0138515000
_diffrn_orient_matrix_UB_21      -0.0164798000
_diffrn_orient_matrix_UB_22      -0.0083076000
_diffrn_orient_matrix_UB_23      -0.0385138000
_diffrn_orient_matrix_UB_31      -0.0386229000
_diffrn_orient_matrix_UB_32      0.0283389000
_diffrn_orient_matrix_UB_33      0.0074855000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.7107
_diffrn_source                   'SuperNova (Mo) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                3025
_reflns_number_total             3685
_reflns_odcompleteness_completeness 99.66
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     26.32
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET)
(compiled Feb  1 2013,16:14:44)
;
_computing_data_collection       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET)
(compiled Feb  1 2013,16:14:44)
;
_computing_data_reduction        
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET)
(compiled Feb  1 2013,16:14:44)
;
_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  
;
SHELX, G.M. Sheldrick, Acta Cryst.
(2008). A64, 112-122
;
_computing_structure_solution    'SUPERFLIP, J. Appl. Cryst. (2007) 40, 786-790'
_refine_diff_density_max         0.790
_refine_diff_density_min         -0.343
_refine_diff_density_rms         0.053
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.035
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     235
_refine_ls_number_reflns         3685
_refine_ls_number_restraints     30
_refine_ls_R_factor_all          0.0599
_refine_ls_R_factor_gt           0.0480
_refine_ls_restrained_S_all      1.055
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
;
 w=1/[σ²(Fo²)+(0.0475P)²+3.1797P]
 where P=(Fo²+2Fc²)/3
;
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1155
_refine_ls_wR_factor_ref         0.1240
_refine_special_details          
;
 ?
;
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All C(H,H,H,H) groups
2. Uiso/Uaniso restraints and constraints
Uanis(C14) \\sim Ueq, Uanis(C15B) \\sim Ueq, Uanis(C15) \\sim Ueq, Uanis(C13)
\\sim Ueq, Uanis(C12) \\sim Ueq: with sigma of 0.01 and sigma for terminal
atoms of 0.02
3. Others
 Fixed Sof: H14A(0.6) H14B(0.6) H14C(0.4) H14D(0.4) C15(0.6) H15A(0.6)
 H15B(0.6) C15B(0.4) H15C(0.4) H15D(0.4) H16A(0.6) H16B(0.6) H16C(0.4) H16D(0.4)
4.a Ternary CH refined with riding coordinates:
 C2(H2), C4(H4)
4.b Secondary CH2 refined with riding coordinates:
 C11(H11A,H11B), C12(H12A,H12B), C13(H13B,H13A), C14(H14A,H14B), C14(H14C,
 H14D), C15(H15A,H15B), C15B(H15C,H15D), C16(H16A,H16B), C16(H16C,H16D)
4.c Aromatic/amide H refined with riding coordinates:
 C6(H6), C7(H7), C8(H8), C9(H9), C10(H10), C18(H18), C19(H19), C20(H20),
 C21(H21), C22(H22)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     iterative
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
S1 S 0.39264(3) 0.47168(4) 0.19823(3) 0.02704(16) Uani 1 1 d . . . . .
N1 N 0.23081(10) 0.50443(11) 0.27014(9) 0.0189(3) Uani 1 1 d . . . . .
N2 N 0.33538(11) 0.42407(11) 0.34195(9) 0.0201(4) Uani 1 1 d . . . . .
C1 C 0.31715(13) 0.46695(13) 0.27241(11) 0.0190(4) Uani 1 1 d . . . . .
C2 C 0.15752(13) 0.46051(14) 0.31724(11) 0.0215(4) Uani 1 1 d . . . . .
H2 H 0.1011 0.4965 0.3111 0.026 Uiso 1 1 calc R U . . .
C3 C 0.18209(15) 0.45759(18) 0.40529(12) 0.0324(5) Uani 1 1 d . . . . .
C4 C 0.28791(14) 0.45420(14) 0.41428(11) 0.0229(4) Uani 1 1 d . . . . .
H4 H 0.3024 0.4101 0.4558 0.027 Uiso 1 1 calc R U . . .
C5 C 0.20256(13) 0.56491(13) 0.20891(10) 0.0188(4) Uani 1 1 d . . . . .
C6 C 0.12116(14) 0.54876(15) 0.16848(11) 0.0245(4) Uani 1 1 d . . . . .
H6 H 0.0875 0.4958 0.1783 0.029 Uiso 1 1 calc R U . . .
C7 C 0.09004(15) 0.61164(16) 0.11347(12) 0.0300(5) Uani 1 1 d . . . . .
H7 H 0.0348 0.6012 0.0874 0.036 Uiso 1 1 calc R U . . .
C8 C 0.14031(15) 0.68955(16) 0.09701(12) 0.0286(5) Uani 1 1 d . . . . .
H8 H 0.1194 0.7313 0.0598 0.034 Uiso 1 1 calc R U . . .
C9 C 0.22201(15) 0.70492(14) 0.13642(12) 0.0264(5) Uani 1 1 d . . . . .
H9 H 0.2567 0.7567 0.1249 0.032 Uiso 1 1 calc R U . . .
C10 C 0.25278(14) 0.64404(14) 0.19294(11) 0.0217(4) Uani 1 1 d . . . . .
H10 H 0.3069 0.6560 0.2202 0.026 Uiso 1 1 calc R U . . .
C11 C 0.13647(16) 0.36072(15) 0.29296(14) 0.0340(5) Uani 1 1 d . . . . .
H11A H 0.0752 0.3560 0.2707 0.041 Uiso 1 1 calc R U . . .
H11B H 0.1808 0.3392 0.2546 0.041 Uiso 1 1 calc R U . . .
C12 C 0.1435(3) 0.3057(2) 0.3681(2) 0.0711(10) Uani 1 1 d . U . . .
H12A H 0.0951 0.2600 0.3704 0.085 Uiso 1 1 calc R U . . .
H12B H 0.2025 0.2750 0.3712 0.085 Uiso 1 1 calc R U . . .
C13 C 0.1336(2) 0.3712(3) 0.43248(18) 0.0683(10) Uani 1 1 d . U . . .
H13B H 0.1619 0.3477 0.4799 0.082 Uiso 1 1 calc R U . . .
H13A H 0.0691 0.3834 0.4429 0.082 Uiso 1 1 calc R U . . .
C14 C 0.1551(2) 0.5455(3) 0.44928(17) 0.0718(12) Uani 1 1 d . U . . .
H14A H 0.1052 0.5328 0.4855 0.086 Uiso 0.6 1 calc R U P A 1
H14B H 0.1344 0.5915 0.4122 0.086 Uiso 0.6 1 calc R U P A 1
H14C H 0.0987 0.5703 0.4274 0.086 Uiso 0.4 1 calc R U P A 2
H14D H 0.1445 0.5318 0.5043 0.086 Uiso 0.4 1 calc R U P A 2
C15 C 0.2419(3) 0.5820(3) 0.4959(3) 0.0427(10) Uani 0.6 1 d . U P B 1
H15A H 0.2415 0.6483 0.5005 0.051 Uiso 0.6 1 calc R U P B 1
H15B H 0.2463 0.5549 0.5477 0.051 Uiso 0.6 1 calc R U P B 1
C15B C 0.2167(4) 0.6012(4) 0.4430(4) 0.0356(14) Uani 0.4 1 d . U P B 2
H15C H 0.2139 0.6442 0.4864 0.043 Uiso 0.4 1 calc R U P B 2
H15D H 0.2093 0.6352 0.3946 0.043 Uiso 0.4 1 calc R U P B 2
C16 C 0.31693(18) 0.54950(16) 0.44312(15) 0.0388(6) Uani 1 1 d . . . . .
H16A H 0.3747 0.5460 0.4714 0.047 Uiso 0.6 1 calc R U P B 1
H16B H 0.3244 0.5910 0.3991 0.047 Uiso 0.6 1 calc R U P B 1
H16C H 0.3600 0.5785 0.4073 0.047 Uiso 0.4 1 calc R U P B 2
H16D H 0.3436 0.5472 0.4953 0.047 Uiso 0.4 1 calc R U P B 2
C17 C 0.40738(12) 0.35801(13) 0.35030(11) 0.0187(4) Uani 1 1 d . . . . .
C18 C 0.47109(14) 0.36588(14) 0.41046(11) 0.0235(4) Uani 1 1 d . . . . .
H18 H 0.4718 0.4182 0.4416 0.028 Uiso 1 1 calc R U . . .
C19 C 0.53395(14) 0.29597(15) 0.42441(12) 0.0274(5) Uani 1 1 d . . . . .
H19 H 0.5756 0.3011 0.4657 0.033 Uiso 1 1 calc R U . . .
C20 C 0.53504(14) 0.21914(14) 0.37758(12) 0.0253(4) Uani 1 1 d . . . . .
H20 H 0.5765 0.1720 0.3875 0.030 Uiso 1 1 calc R U . . .
C21 C 0.47366(14) 0.21281(14) 0.31557(12) 0.0264(5) Uani 1 1 d . . . . .
H21 H 0.4755 0.1620 0.2827 0.032 Uiso 1 1 calc R U . . .
C22 C 0.40970(14) 0.28129(14) 0.30207(12) 0.0240(4) Uani 1 1 d . . . . .
H22 H 0.3683 0.2759 0.2607 0.029 Uiso 1 1 calc R U . . .


_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 1.6746(19) . ?
N1 C1 1.369(2) . ?
N1 C2 1.479(2) . ?
N1 C5 1.427(2) . ?
N2 C1 1.366(2) . ?
N2 C4 1.479(2) . ?
N2 C17 1.430(2) . ?
C2 H2 0.9800 . ?
C2 C3 1.543(3) . ?
C2 C11 1.545(3) . ?
C3 C4 1.546(3) . ?
C3 C13 1.516(4) . ?
C3 C14 1.537(4) . ?
C4 H4 0.9800 . ?
C4 C16 1.535(3) . ?
C5 C6 1.389(3) . ?
C5 C10 1.393(3) . ?
C6 H6 0.9300 . ?
C6 C7 1.388(3) . ?
C7 H7 0.9300 . ?
C7 C8 1.380(3) . ?
C8 H8 0.9300 . ?
C8 C9 1.382(3) . ?
C9 H9 0.9300 . ?
C9 C10 1.385(3) . ?
C10 H10 0.9300 . ?
C11 H11A 0.9700 . ?
C11 H11B 0.9700 . ?
C11 C12 1.515(4) . ?
C12 H12A 0.9700 . ?
C12 H12B 0.9700 . ?
C12 C13 1.461(5) . ?
C13 H13B 0.9700 . ?
C13 H13A 0.9700 . ?
C14 H14A 0.9700 . ?
C14 H14B 0.9700 . ?
C14 H14C 0.9700 . ?
C14 H14D 0.9700 . ?
C14 C15 1.583(5) . ?
C14 C15B 1.214(7) . ?
C15 H15A 0.9700 . ?
C15 H15B 0.9700 . ?
C15 C16 1.490(5) . ?
C15B H15C 0.9700 . ?
C15B H15D 0.9700 . ?
C15B C16 1.640(6) . ?
C16 H16A 0.9700 . ?
C16 H16B 0.9700 . ?
C16 H16C 0.9700 . ?
C16 H16D 0.9700 . ?
C17 C18 1.386(3) . ?
C17 C22 1.389(3) . ?
C18 H18 0.9300 . ?
C18 C19 1.390(3) . ?
C19 H19 0.9300 . ?
C19 C20 1.376(3) . ?
C20 H20 0.9300 . ?
C20 C21 1.385(3) . ?
C21 H21 0.9300 . ?
C21 C22 1.384(3) . ?
C22 H22 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
C1 N1 C2 118.09(15) . . ?
C1 N1 C5 122.10(15) . . ?
C5 N1 C2 117.24(15) . . ?
C1 N2 C4 119.73(15) . . ?
C1 N2 C17 122.49(15) . . ?
C17 N2 C4 117.32(15) . . ?
N1 C1 S1 124.21(14) . . ?
N2 C1 S1 123.12(14) . . ?
N2 C1 N1 112.66(16) . . ?
N1 C2 H2 108.2 . . ?
N1 C2 C3 111.89(16) . . ?
N1 C2 C11 113.96(17) . . ?
C3 C2 H2 108.2 . . ?
C3 C2 C11 106.26(18) . . ?
C11 C2 H2 108.2 . . ?
C2 C3 C4 109.10(16) . . ?
C13 C3 C2 102.3(2) . . ?
C13 C3 C4 113.9(2) . . ?
C13 C3 C14 115.3(3) . . ?
C14 C3 C2 113.1(2) . . ?
C14 C3 C4 103.4(2) . . ?
N2 C4 C3 113.01(16) . . ?
N2 C4 H4 107.8 . . ?
N2 C4 C16 114.09(18) . . ?
C3 C4 H4 107.8 . . ?
C16 C4 C3 106.01(18) . . ?
C16 C4 H4 107.8 . . ?
C6 C5 N1 120.16(17) . . ?
C6 C5 C10 119.34(18) . . ?
C10 C5 N1 120.34(17) . . ?
C5 C6 H6 120.0 . . ?
C7 C6 C5 120.0(2) . . ?
C7 C6 H6 120.0 . . ?
C6 C7 H7 119.7 . . ?
C8 C7 C6 120.7(2) . . ?
C8 C7 H7 119.7 . . ?
C7 C8 H8 120.4 . . ?
C7 C8 C9 119.30(19) . . ?
C9 C8 H8 120.4 . . ?
C8 C9 H9 119.6 . . ?
C8 C9 C10 120.7(2) . . ?
C10 C9 H9 119.6 . . ?
C5 C10 H10 120.0 . . ?
C9 C10 C5 119.93(19) . . ?
C9 C10 H10 120.0 . . ?
C2 C11 H11A 110.7 . . ?
C2 C11 H11B 110.7 . . ?
H11A C11 H11B 108.8 . . ?
C12 C11 C2 105.1(2) . . ?
C12 C11 H11A 110.7 . . ?
C12 C11 H11B 110.7 . . ?
C11 C12 H12A 110.5 . . ?
C11 C12 H12B 110.5 . . ?
H12A C12 H12B 108.7 . . ?
C13 C12 C11 106.3(2) . . ?
C13 C12 H12A 110.5 . . ?
C13 C12 H12B 110.5 . . ?
C3 C13 H13B 110.6 . . ?
C3 C13 H13A 110.6 . . ?
C12 C13 C3 105.6(2) . . ?
C12 C13 H13B 110.6 . . ?
C12 C13 H13A 110.6 . . ?
H13B C13 H13A 108.7 . . ?
C3 C14 H14A 109.9 . . ?
C3 C14 H14B 109.9 . . ?
C3 C14 H14C 109.8 . . ?
C3 C14 H14D 109.8 . . ?
C3 C14 C15 108.8(2) . . ?
H14A C14 H14B 108.3 . . ?
H14C C14 H14D 108.3 . . ?
C15 C14 H14A 109.9 . . ?
C15 C14 H14B 109.9 . . ?
C15B C14 C3 109.2(3) . . ?
C15B C14 H14C 109.8 . . ?
C15B C14 H14D 109.8 . . ?
C14 C15 H15A 111.8 . . ?
C14 C15 H15B 111.8 . . ?
H15A C15 H15B 109.5 . . ?
C16 C15 C14 99.9(3) . . ?
C16 C15 H15A 111.8 . . ?
C16 C15 H15B 111.8 . . ?
C14 C15B H15C 109.6 . . ?
C14 C15B H15D 109.6 . . ?
C14 C15B C16 110.2(4) . . ?
H15C C15B H15D 108.1 . . ?
C16 C15B H15C 109.6 . . ?
C16 C15B H15D 109.6 . . ?
C4 C16 C15B 100.0(3) . . ?
C4 C16 H16A 110.5 . . ?
C4 C16 H16B 110.5 . . ?
C4 C16 H16C 111.8 . . ?
C4 C16 H16D 111.8 . . ?
C15 C16 C4 106.3(3) . . ?
C15 C16 H16A 110.5 . . ?
C15 C16 H16B 110.5 . . ?
C15B C16 H16C 111.8 . . ?
C15B C16 H16D 111.8 . . ?
H16A C16 H16B 108.7 . . ?
H16C C16 H16D 109.5 . . ?
C18 C17 N2 120.41(17) . . ?
C18 C17 C22 119.21(18) . . ?
C22 C17 N2 120.18(16) . . ?
C17 C18 H18 119.9 . . ?
C17 C18 C19 120.28(19) . . ?
C19 C18 H18 119.9 . . ?
C18 C19 H19 119.8 . . ?
C20 C19 C18 120.45(19) . . ?
C20 C19 H19 119.8 . . ?
C19 C20 H20 120.4 . . ?
C19 C20 C21 119.26(19) . . ?
C21 C20 H20 120.4 . . ?
C20 C21 H21 119.6 . . ?
C22 C21 C20 120.71(19) . . ?
C22 C21 H21 119.6 . . ?
C17 C22 H22 120.0 . . ?
C21 C22 C17 120.01(18) . . ?
C21 C22 H22 120.0 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
N1 C2 C3 C4 -28.5(2) . . . . ?
N1 C2 C3 C13 -149.5(2) . . . . ?
N1 C2 C3 C14 85.9(2) . . . . ?
N1 C2 C11 C12 127.3(2) . . . . ?
N1 C5 C6 C7 174.71(18) . . . . ?
N1 C5 C10 C9 -176.37(17) . . . . ?
N2 C4 C16 C15 160.1(2) . . . . ?
N2 C4 C16 C15B 122.2(3) . . . . ?
N2 C17 C18 C19 172.07(18) . . . . ?
N2 C17 C22 C21 -173.26(18) . . . . ?
C1 N1 C2 C3 58.6(2) . . . . ?
C1 N1 C2 C11 -62.0(2) . . . . ?
C1 N1 C5 C6 128.8(2) . . . . ?
C1 N1 C5 C10 -55.8(3) . . . . ?
C1 N2 C4 C3 52.4(2) . . . . ?
C1 N2 C4 C16 -68.8(2) . . . . ?
C1 N2 C17 C18 129.3(2) . . . . ?
C1 N2 C17 C22 -55.9(3) . . . . ?
C2 N1 C1 S1 150.30(15) . . . . ?
C2 N1 C1 N2 -29.2(2) . . . . ?
C2 N1 C5 C6 -32.6(3) . . . . ?
C2 N1 C5 C10 142.78(18) . . . . ?
C2 C3 C4 N2 -19.1(3) . . . . ?
C2 C3 C4 C16 106.6(2) . . . . ?
C2 C3 C13 C12 37.6(3) . . . . ?
C2 C3 C14 C15 -128.0(3) . . . . ?
C2 C3 C14 C15B -85.9(4) . . . . ?
C2 C11 C12 C13 19.9(3) . . . . ?
C3 C2 C11 C12 3.6(2) . . . . ?
C3 C4 C16 C15 35.0(3) . . . . ?
C3 C4 C16 C15B -2.8(3) . . . . ?
C3 C14 C15 C16 30.6(4) . . . . ?
C3 C14 C15B C16 -35.2(6) . . . . ?
C4 N2 C1 S1 153.50(15) . . . . ?
C4 N2 C1 N1 -27.0(2) . . . . ?
C4 N2 C17 C18 -42.9(2) . . . . ?
C4 N2 C17 C22 131.90(19) . . . . ?
C4 C3 C13 C12 -80.0(3) . . . . ?
C4 C3 C14 C15 -10.2(3) . . . . ?
C4 C3 C14 C15B 32.0(5) . . . . ?
C5 N1 C1 S1 -11.0(3) . . . . ?
C5 N1 C1 N2 169.53(17) . . . . ?
C5 N1 C2 C3 -139.13(18) . . . . ?
C5 N1 C2 C11 100.3(2) . . . . ?
C5 C6 C7 C8 1.5(3) . . . . ?
C6 C5 C10 C9 -0.9(3) . . . . ?
C6 C7 C8 C9 -0.5(3) . . . . ?
C7 C8 C9 C10 -1.2(3) . . . . ?
C8 C9 C10 C5 1.9(3) . . . . ?
C10 C5 C6 C7 -0.7(3) . . . . ?
C11 C2 C3 C4 96.4(2) . . . . ?
C11 C2 C3 C13 -24.5(2) . . . . ?
C11 C2 C3 C14 -149.1(2) . . . . ?
C11 C12 C13 C3 -36.5(3) . . . . ?
C13 C3 C4 N2 94.5(2) . . . . ?
C13 C3 C4 C16 -139.9(2) . . . . ?
C13 C3 C14 C15 114.8(3) . . . . ?
C13 C3 C14 C15B 156.9(4) . . . . ?
C14 C3 C4 N2 -139.7(2) . . . . ?
C14 C3 C4 C16 -14.0(3) . . . . ?
C14 C3 C13 C12 160.7(2) . . . . ?
C14 C15 C16 C4 -39.1(4) . . . . ?
C14 C15 C16 C15B 45.9(4) . . . . ?
C14 C15B C16 C4 24.3(5) . . . . ?
C14 C15B C16 C15 -79.6(6) . . . . ?
C15 C14 C15B C16 61.5(4) . . . . ?
C15B C14 C15 C16 -67.0(5) . . . . ?
C17 N2 C1 S1 -18.5(3) . . . . ?
C17 N2 C1 N1 160.94(16) . . . . ?
C17 N2 C4 C3 -135.14(18) . . . . ?
C17 N2 C4 C16 103.6(2) . . . . ?
C17 C18 C19 C20 1.5(3) . . . . ?
C18 C17 C22 C21 1.6(3) . . . . ?
C18 C19 C20 C21 1.0(3) . . . . ?
C19 C20 C21 C22 -2.1(3) . . . . ?
C20 C21 C22 C17 0.9(3) . . . . ?
C22 C17 C18 C19 -2.7(3) . . . . ?

_database_code_depnum_ccdc_archive 'CCDC 973596'
#######################################################################
#
#                 Cambridge Crystallographic Data Centre
#                                CCDC 
# 
#######################################################################
# 
#  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.
#
#  This CIF is provided on the understanding that it is used for bona
#  fide research purposes only. It may contain copyright material
#  of the CCDC or of third parties, and may not be copied or further
#  disseminated in any form, whether machine-readable or not,
#  except for the purpose of generating routine backup copies
#  on your local computer system.
# 
#  For further information on the CCDC, data deposition and
#  data retrieval see:
#                         www.ccdc.cam.ac.uk
#
#  Bona fide researchers may freely download Mercury and enCIFer
#  from this site to visualise CIF-encoded structures and 
#  to carry out CIF format checking respectively.
#
data_p21n
_audit_creation_date             2013-10-30
_audit_creation_method           
;
Olex2 1.2
(compiled 2013.09.17 svn.r2790 for OlexSys, GUI svn.r4601)
;
_shelxl_version_number           2013-2
_chemical_name_common            ?
_chemical_name_systematic        
;
 ?
;
_chemical_formula_moiety         'C22 H25 N2, B F4'
_chemical_formula_sum            'C22 H25 B F4 N2'
_chemical_formula_weight         404.25
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 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'
B B 0.0013 0.0007 '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'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 1 21/n 1'
_space_group_name_Hall           '-P 2yn'
loop_
_space_group_symop_operation_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                   9.802(13)
_cell_length_b                   19.00(3)
_cell_length_c                   11.112(15)
_cell_angle_alpha                90
_cell_angle_beta                 91.156(12)
_cell_angle_gamma                90
_cell_volume                     2069(5)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    2209
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      25.48
_cell_measurement_theta_min      2.74
_shelx_estimated_absorpt_T_max   0.982
_shelx_estimated_absorpt_T_min   0.974
_exptl_absorpt_coefficient_mu    0.101
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   ?
_exptl_crystal_colour            ?
_exptl_crystal_density_diffrn    1.298
_exptl_crystal_density_meas      .
_exptl_crystal_density_method    ?
_exptl_crystal_description       ?
_exptl_crystal_F_000             848
_exptl_crystal_size_max          0.26
_exptl_crystal_size_mid          0.23
_exptl_crystal_size_min          0.18
_exptl_special_details           
;
 ?
;
_exptl_transmission_factor_max   0.982
_exptl_transmission_factor_min   0.974
_diffrn_reflns_av_R_equivalents  0.1405
_diffrn_reflns_av_unetI/netI     0.2318
_diffrn_reflns_Laue_measured_fraction_full 0.944
_diffrn_reflns_Laue_measured_fraction_max 0.956
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       22
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_number            9069
_diffrn_reflns_point_group_measured_fraction_full 0.944
_diffrn_reflns_point_group_measured_fraction_max 0.956
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         25.095
_diffrn_reflns_theta_min         2.123
_diffrn_ambient_temperature      296.15
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.944
_diffrn_measured_fraction_theta_max 0.956
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                1351
_reflns_number_total             3527
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       ?
_computing_data_collection       ?
_computing_data_reduction        ?
_computing_molecular_graphics    
;
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  
;
SHELX, G.M. Sheldrick, Acta Cryst.
(2008). A64, 112-122
;
_computing_structure_solution    
;
SHELX, G.M. Sheldrick, Acta Cryst.
(2008). A64, 112-122
;
_refine_diff_density_max         0.181
_refine_diff_density_min         -0.176
_refine_diff_density_rms         0.040
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.162
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     290
_refine_ls_number_reflns         3527
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.2913
_refine_ls_R_factor_gt           0.1613
_refine_ls_restrained_S_all      1.162
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
;
 w=1/[σ²(Fo²)+3.9347P]
 where P=(Fo²+2Fc²)/3
;
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1680
_refine_ls_wR_factor_ref         0.1933
_refine_special_details          
;
 ?
;
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
2. Others
 Sof(F1B)=Sof(F2B)=Sof(F3B)=1-FVAR(1)
 Sof(F1A)=Sof(F3A)=Sof(F2A)=FVAR(1)
3.a Ternary CH refined with riding coordinates:
 C4(H4), C2(H2)
3.b Secondary CH2 refined with riding coordinates:
 C16(H16A,H16B), C15(H15A,H15B), C14(H14A,H14B), C13(H13A,H13B), C12(H12A,
 H12B), C11(H11A,H11B)
3.c Aromatic/amide H refined with riding coordinates:
 C22(H22), C21(H21), C20(H20), C19(H19), C18(H18), C1(H1), C10(H10), C9(H9),
 C8(H8), C7(H7), C6(H6)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
C22 C 0.6744(7) 0.3560(4) 0.8707(8) 0.056(2) Uani 1 1 d . . . A 1
H22 H 0.6982 0.3158 0.9138 0.067 Uiso 1 1 calc R U . A 1
C21 C 0.6658(8) 0.4204(5) 0.9291(8) 0.069(3) Uani 1 1 d . . . A 1
H21 H 0.6831 0.4232 1.0116 0.082 Uiso 1 1 calc R U . A 1
C20 C 0.6319(8) 0.4798(5) 0.8654(11) 0.075(3) Uani 1 1 d . . . A 1
H20 H 0.6236 0.5225 0.9054 0.090 Uiso 1 1 calc R U . A 1
C19 C 0.6100(8) 0.4768(5) 0.7424(10) 0.077(3) Uani 1 1 d . . . A 1
H19 H 0.5912 0.5177 0.6993 0.092 Uiso 1 1 calc R U . A 1
C18 C 0.6160(7) 0.4122(4) 0.6829(8) 0.058(2) Uani 1 1 d . . . A 1
H18 H 0.5993 0.4094 0.6004 0.070 Uiso 1 1 calc R U . A 1
C17 C 0.6476(7) 0.3519(4) 0.7491(8) 0.044(2) Uani 1 1 d . . . A 1
C4 C 0.7223(7) 0.2720(4) 0.5764(7) 0.049(2) Uani 1 1 d . . . B 1
H4 H 0.6699 0.2899 0.5069 0.059 Uiso 1 1 calc R U . B 1
C16 C 0.8645(7) 0.3059(4) 0.5829(7) 0.062(2) Uani 1 1 d . . . B 1
H16A H 0.8999 0.3128 0.5029 0.074 Uiso 1 1 calc R U . B 1
H16B H 0.8614 0.3510 0.6237 0.074 Uiso 1 1 calc R U . B 1
C15 C 0.9516(8) 0.2543(4) 0.6534(8) 0.083(3) Uani 1 1 d . . . B 1
H15A H 0.9598 0.2689 0.7369 0.100 Uiso 1 1 calc R U . B 1
H15B H 1.0423 0.2520 0.6203 0.100 Uiso 1 1 calc R U . B 1
C14 C 0.8830(7) 0.1832(4) 0.6446(7) 0.063(2) Uani 1 1 d . . . B 1
H14A H 0.8564 0.1671 0.7237 0.075 Uiso 1 1 calc R U . B 1
H14B H 0.9444 0.1487 0.6108 0.075 Uiso 1 1 calc R U . B 1
C3 C 0.7545(7) 0.1930(4) 0.5609(7) 0.046(2) Uani 1 1 d . . . B 1
C13 C 0.7801(8) 0.1756(4) 0.4275(7) 0.068(3) Uani 1 1 d . . . B 1
H13A H 0.7724 0.2179 0.3788 0.081 Uiso 1 1 calc R U . B 1
H13B H 0.8710 0.1564 0.4187 0.081 Uiso 1 1 calc R U . B 1
C12 C 0.6723(9) 0.1215(5) 0.3871(7) 0.085(3) Uani 1 1 d . . . B 1
H12A H 0.6403 0.1311 0.3055 0.102 Uiso 1 1 calc R U . B 1
H12B H 0.7092 0.0742 0.3905 0.102 Uiso 1 1 calc R U . B 1
C11 C 0.5582(8) 0.1302(5) 0.4754(7) 0.073(3) Uani 1 1 d . . . B 1
H11A H 0.5030 0.0880 0.4800 0.088 Uiso 1 1 calc R U . B 1
H11B H 0.5001 0.1698 0.4539 0.088 Uiso 1 1 calc R U . B 1
C2 C 0.6364(7) 0.1436(4) 0.5932(7) 0.046(2) Uani 1 1 d . . . B 1
H2 H 0.6762 0.0988 0.6198 0.055 Uiso 1 1 calc R U . B 1
C1 C 0.5664(6) 0.2355(4) 0.7309(6) 0.042(2) Uani 1 1 d . . . C 1
H1 H 0.5129 0.2483 0.7955 0.051 Uiso 1 1 calc R U . C 1
C5 C 0.4511(7) 0.1256(4) 0.7434(6) 0.0405(19) Uani 1 1 d . . . D 1
C10 C 0.3167(7) 0.1448(4) 0.7403(6) 0.051(2) Uani 1 1 d . . . D 1
H10 H 0.2902 0.1865 0.7029 0.061 Uiso 1 1 calc R U . D 1
C9 C 0.2197(8) 0.1021(5) 0.7930(7) 0.066(3) Uani 1 1 d . . . D 1
H9 H 0.1284 0.1155 0.7915 0.080 Uiso 1 1 calc R U . D 1
C8 C 0.2587(9) 0.0399(5) 0.8476(8) 0.072(3) Uani 1 1 d . . . D 1
H8 H 0.1937 0.0114 0.8833 0.086 Uiso 1 1 calc R U . D 1
C7 C 0.3927(9) 0.0200(4) 0.8493(7) 0.071(3) Uani 1 1 d . . . D 1
H7 H 0.4182 -0.0225 0.8848 0.085 Uiso 1 1 calc R U . D 1
C6 C 0.4918(8) 0.0629(4) 0.7985(7) 0.059(2) Uani 1 1 d . . . D 1
H6 H 0.5832 0.0498 0.8012 0.071 Uiso 1 1 calc R U . D 1
F1A F 0.879(3) 0.1086(13) 0.9650(19) 0.112(11) Uani 0.50(3) 1 d . . P E 1
F4 F 0.6991(6) 0.1805(4) 0.9479(6) 0.144(3) Uani 1 1 d . . . . .
F3A F 0.802(3) 0.155(2) 1.127(2) 0.144(16) Uani 0.50(3) 1 d . . P E 1
F2A F 0.875(3) 0.2218(11) 0.988(4) 0.177(15) Uani 0.50(3) 1 d . . P E 1
N2 N 0.6476(5) 0.2838(3) 0.6889(5) 0.0424(16) Uani 1 1 d . . . . .
N1 N 0.5525(5) 0.1704(3) 0.6910(5) 0.0416(16) Uani 1 1 d . . . . .
B2 B 0.8164(10) 0.1627(7) 1.0065(14) 0.061(3) Uani 1 1 d . . . . .
F1B F 0.793(5) 0.0998(15) 1.009(4) 0.26(2) Uani 0.50(3) 1 d . . P E 2
F2B F 0.9317(17) 0.178(3) 0.9514(18) 0.187(19) Uani 0.50(3) 1 d . . P E 2
F3B F 0.834(3) 0.190(2) 1.110(3) 0.17(2) Uani 0.50(3) 1 d . . P E 2


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C22 H22 0.9300 . ?
C22 C21 1.388(10) . ?
C22 C17 1.373(9) . ?
C21 H21 0.9300 . ?
C21 C20 1.370(11) . ?
C20 H20 0.9300 . ?
C20 C19 1.380(11) . ?
C19 H19 0.9300 . ?
C19 C18 1.396(10) . ?
C18 H18 0.9300 . ?
C18 C17 1.393(9) . ?
C17 N2 1.457(8) . ?
C4 H4 0.9800 . ?
C4 C16 1.536(9) . ?
C4 C3 1.544(9) . ?
C4 N2 1.478(8) . ?
C16 H16A 0.9700 . ?
C16 H16B 0.9700 . ?
C16 C15 1.509(9) . ?
C15 H15A 0.9700 . ?
C15 H15B 0.9700 . ?
C15 C14 1.513(9) . ?
C14 H14A 0.9700 . ?
C14 H14B 0.9700 . ?
C14 C3 1.562(9) . ?
C3 C13 1.544(9) . ?
C3 C2 1.538(9) . ?
C13 H13A 0.9700 . ?
C13 H13B 0.9700 . ?
C13 C12 1.535(9) . ?
C12 H12A 0.9700 . ?
C12 H12B 0.9700 . ?
C12 C11 1.512(9) . ?
C11 H11A 0.9700 . ?
C11 H11B 0.9700 . ?
C11 C2 1.525(9) . ?
C2 H2 0.9800 . ?
C2 N1 1.467(8) . ?
C1 H1 0.9300 . ?
C1 N2 1.307(8) . ?
C1 N1 1.320(8) . ?
C5 C10 1.367(9) . ?
C5 C6 1.394(9) . ?
C5 N1 1.440(8) . ?
C10 H10 0.9300 . ?
C10 C9 1.387(9) . ?
C9 H9 0.9300 . ?
C9 C8 1.380(10) . ?
C8 H8 0.9300 . ?
C8 C7 1.367(10) . ?
C7 H7 0.9300 . ?
C7 C6 1.395(10) . ?
C6 H6 0.9300 . ?
F1A B2 1.289(18) . ?
F4 B2 1.353(11) . ?
F3A B2 1.36(3) . ?
F2A B2 1.28(2) . ?
B2 F1B 1.22(2) . ?
B2 F2B 1.329(19) . ?
B2 F3B 1.26(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
C21 C22 H22 120.0 . . ?
C17 C22 H22 120.0 . . ?
C17 C22 C21 119.9(8) . . ?
C22 C21 H21 120.0 . . ?
C20 C21 C22 120.0(9) . . ?
C20 C21 H21 120.0 . . ?
C21 C20 H20 119.7 . . ?
C21 C20 C19 120.6(9) . . ?
C19 C20 H20 119.7 . . ?
C20 C19 H19 120.1 . . ?
C20 C19 C18 119.9(9) . . ?
C18 C19 H19 120.1 . . ?
C19 C18 H18 120.5 . . ?
C17 C18 C19 119.0(8) . . ?
C17 C18 H18 120.5 . . ?
C22 C17 C18 120.6(8) . . ?
C22 C17 N2 120.1(7) . . ?
C18 C17 N2 119.3(8) . . ?
C16 C4 H4 110.7 . . ?
C16 C4 C3 103.1(6) . . ?
C3 C4 H4 110.7 . . ?
N2 C4 H4 110.7 . . ?
N2 C4 C16 111.2(6) . . ?
N2 C4 C3 110.3(6) . . ?
C4 C16 H16A 110.8 . . ?
C4 C16 H16B 110.8 . . ?
H16A C16 H16B 108.9 . . ?
C15 C16 C4 104.8(6) . . ?
C15 C16 H16A 110.8 . . ?
C15 C16 H16B 110.8 . . ?
C16 C15 H15A 110.2 . . ?
C16 C15 H15B 110.2 . . ?
C16 C15 C14 107.5(6) . . ?
H15A C15 H15B 108.5 . . ?
C14 C15 H15A 110.2 . . ?
C14 C15 H15B 110.2 . . ?
C15 C14 H14A 110.4 . . ?
C15 C14 H14B 110.4 . . ?
C15 C14 C3 106.5(6) . . ?
H14A C14 H14B 108.6 . . ?
C3 C14 H14A 110.4 . . ?
C3 C14 H14B 110.4 . . ?
C4 C3 C14 102.4(6) . . ?
C13 C3 C4 110.7(6) . . ?
C13 C3 C14 113.7(6) . . ?
C2 C3 C4 114.3(6) . . ?
C2 C3 C14 112.9(6) . . ?
C2 C3 C13 103.4(6) . . ?
C3 C13 H13A 110.2 . . ?
C3 C13 H13B 110.2 . . ?
H13A C13 H13B 108.5 . . ?
C12 C13 C3 107.5(6) . . ?
C12 C13 H13A 110.2 . . ?
C12 C13 H13B 110.2 . . ?
C13 C12 H12A 110.8 . . ?
C13 C12 H12B 110.8 . . ?
H12A C12 H12B 108.9 . . ?
C11 C12 C13 104.5(7) . . ?
C11 C12 H12A 110.8 . . ?
C11 C12 H12B 110.8 . . ?
C12 C11 H11A 111.3 . . ?
C12 C11 H11B 111.3 . . ?
C12 C11 C2 102.1(6) . . ?
H11A C11 H11B 109.2 . . ?
C2 C11 H11A 111.3 . . ?
C2 C11 H11B 111.3 . . ?
C3 C2 H2 107.7 . . ?
C11 C2 C3 105.6(6) . . ?
C11 C2 H2 107.7 . . ?
N1 C2 C3 113.4(6) . . ?
N1 C2 C11 114.5(6) . . ?
N1 C2 H2 107.7 . . ?
N2 C1 H1 116.7 . . ?
N2 C1 N1 126.7(7) . . ?
N1 C1 H1 116.7 . . ?
C10 C5 C6 120.3(7) . . ?
C10 C5 N1 120.3(7) . . ?
C6 C5 N1 119.3(6) . . ?
C5 C10 H10 119.9 . . ?
C5 C10 C9 120.2(8) . . ?
C9 C10 H10 119.9 . . ?
C10 C9 H9 120.0 . . ?
C8 C9 C10 120.0(8) . . ?
C8 C9 H9 120.0 . . ?
C9 C8 H8 120.0 . . ?
C7 C8 C9 120.0(8) . . ?
C7 C8 H8 120.0 . . ?
C8 C7 H7 119.7 . . ?
C8 C7 C6 120.7(8) . . ?
C6 C7 H7 119.7 . . ?
C5 C6 H6 120.6 . . ?
C7 C6 C5 118.8(7) . . ?
C7 C6 H6 120.6 . . ?
C17 N2 C4 121.8(6) . . ?
C1 N2 C17 117.0(6) . . ?
C1 N2 C4 120.8(6) . . ?
C1 N1 C2 121.2(6) . . ?
C1 N1 C5 119.1(6) . . ?
C5 N1 C2 119.7(6) . . ?
F1A B2 F4 115.9(15) . . ?
F1A B2 F3A 109(2) . . ?
F4 B2 F3A 113.4(16) . . ?
F2A B2 F1A 114.8(19) . . ?
F2A B2 F4 94.9(15) . . ?
F2A B2 F3A 108(2) . . ?
F1B B2 F4 96(2) . . ?
F1B B2 F2B 113(2) . . ?
F1B B2 F3B 113(3) . . ?
F2B B2 F4 116.4(15) . . ?
F3B B2 F4 115.7(18) . . ?
F3B B2 F2B 103.1(18) . . ?

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
C22 C21 C20 C19 -1.9(13) . . . . ?
C22 C17 N2 C4 -131.6(7) . . . . ?
C22 C17 N2 C1 55.8(9) . . . . ?
C21 C22 C17 C18 2.0(11) . . . . ?
C21 C22 C17 N2 -175.9(6) . . . . ?
C21 C20 C19 C18 3.0(13) . . . . ?
C20 C19 C18 C17 -1.6(12) . . . . ?
C19 C18 C17 C22 -0.9(11) . . . . ?
C19 C18 C17 N2 177.0(6) . . . . ?
C18 C17 N2 C4 50.5(9) . . . . ?
C18 C17 N2 C1 -122.1(7) . . . . ?
C17 C22 C21 C20 -0.6(12) . . . . ?
C4 C16 C15 C14 21.7(9) . . . . ?
C4 C3 C13 C12 -119.3(7) . . . . ?
C4 C3 C2 C11 93.1(7) . . . . ?
C4 C3 C2 N1 -33.0(9) . . . . ?
C16 C4 C3 C14 38.4(7) . . . . ?
C16 C4 C3 C13 -83.1(7) . . . . ?
C16 C4 C3 C2 160.7(6) . . . . ?
C16 C4 N2 C17 43.3(9) . . . . ?
C16 C4 N2 C1 -144.4(6) . . . . ?
C16 C15 C14 C3 2.6(9) . . . . ?
C15 C14 C3 C4 -25.5(8) . . . . ?
C15 C14 C3 C13 93.9(8) . . . . ?
C15 C14 C3 C2 -148.8(7) . . . . ?
C14 C3 C13 C12 126.1(7) . . . . ?
C14 C3 C2 C11 -150.5(6) . . . . ?
C14 C3 C2 N1 83.4(7) . . . . ?
C3 C4 C16 C15 -37.6(8) . . . . ?
C3 C4 N2 C17 157.0(6) . . . . ?
C3 C4 N2 C1 -30.7(9) . . . . ?
C3 C13 C12 C11 21.6(9) . . . . ?
C3 C2 N1 C1 10.4(9) . . . . ?
C3 C2 N1 C5 -170.8(6) . . . . ?
C13 C3 C2 C11 -27.2(7) . . . . ?
C13 C3 C2 N1 -153.3(6) . . . . ?
C13 C12 C11 C2 -37.9(9) . . . . ?
C12 C11 C2 C3 40.9(8) . . . . ?
C12 C11 C2 N1 166.4(6) . . . . ?
C11 C2 N1 C1 -110.8(8) . . . . ?
C11 C2 N1 C5 68.0(8) . . . . ?
C2 C3 C13 C12 3.4(8) . . . . ?
C5 C10 C9 C8 -0.6(12) . . . . ?
C10 C5 C6 C7 0.5(11) . . . . ?
C10 C5 N1 C2 -120.3(7) . . . . ?
C10 C5 N1 C1 58.5(9) . . . . ?
C10 C9 C8 C7 -0.3(13) . . . . ?
C9 C8 C7 C6 1.4(13) . . . . ?
C8 C7 C6 C5 -1.4(12) . . . . ?
C6 C5 C10 C9 0.5(11) . . . . ?
C6 C5 N1 C2 60.5(9) . . . . ?
C6 C5 N1 C1 -120.7(7) . . . . ?
N2 C4 C16 C15 80.5(8) . . . . ?
N2 C4 C3 C14 -80.4(7) . . . . ?
N2 C4 C3 C13 158.1(6) . . . . ?
N2 C4 C3 C2 41.9(8) . . . . ?
N2 C1 N1 C2 2.8(11) . . . . ?
N2 C1 N1 C5 -176.0(6) . . . . ?
N1 C1 N2 C17 -178.8(7) . . . . ?
N1 C1 N2 C4 8.6(11) . . . . ?
N1 C5 C10 C9 -178.7(6) . . . . ?
N1 C5 C6 C7 179.7(7) . . . . ?

_database_code_depnum_ccdc_archive 'CCDC 973597'
#######################################################################
#
#                 Cambridge Crystallographic Data Centre
#                                CCDC 
# 
#######################################################################
# 
#  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.
#
#  This CIF is provided on the understanding that it is used for bona
#  fide research purposes only. It may contain copyright material
#  of the CCDC or of third parties, and may not be copied or further
#  disseminated in any form, whether machine-readable or not,
#  except for the purpose of generating routine backup copies
#  on your local computer system.
# 
#  For further information on the CCDC, data deposition and
#  data retrieval see:
#                         www.ccdc.cam.ac.uk
#
#  Bona fide researchers may freely download Mercury and enCIFer
#  from this site to visualise CIF-encoded structures and 
#  to carry out CIF format checking respectively.
#
data_xiangk0923
_audit_creation_date             2013-10-30
_audit_creation_method           
;
Olex2 1.2
(compiled 2013.09.17 svn.r2790 for OlexSys, GUI svn.r4601)
;
_shelxl_version_number           2013-2
_chemical_name_common            ?
_chemical_name_systematic        
;
 ?
;
_chemical_formula_moiety         'C22 H24 Au Cl N2'
_chemical_formula_sum            'C22 H24 Au Cl N2'
_chemical_formula_weight         548.85
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Au Au -4.4197 7.2980 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cl Cl 0.3639 0.7018 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 1 21/n 1'
_space_group_name_Hall           '-P 2yn'
loop_
_space_group_symop_operation_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                   19.6622(8)
_cell_length_b                   10.8065(4)
_cell_length_c                   19.9969(9)
_cell_angle_alpha                90
_cell_angle_beta                 105.351(4)
_cell_angle_gamma                90
_cell_volume                     4097.3(3)
_cell_formula_units_Z            8
_cell_measurement_reflns_used    ?
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      ?
_cell_measurement_theta_min      ?
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    14.737
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_type   ?
_exptl_absorpt_process_details   ?
_exptl_crystal_colour            ?
_exptl_crystal_density_diffrn    1.779
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       ?
_exptl_crystal_F_000             2128
_exptl_crystal_size_max          ?
_exptl_crystal_size_mid          ?
_exptl_crystal_size_min          ?
_exptl_special_details           
;
 ?
;
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0531
_diffrn_reflns_av_unetI/netI     0.0471
_diffrn_reflns_Laue_measured_fraction_full 0.976
_diffrn_reflns_Laue_measured_fraction_max 0.972
_diffrn_reflns_limit_h_max       19
_diffrn_reflns_limit_h_min       -24
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       24
_diffrn_reflns_limit_l_min       -24
_diffrn_reflns_number            24697
_diffrn_reflns_point_group_measured_fraction_full 0.976
_diffrn_reflns_point_group_measured_fraction_max 0.972
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         72.582
_diffrn_reflns_theta_min         3.677
_diffrn_ambient_temperature      293(2)
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.976
_diffrn_measured_fraction_theta_max 0.972
_diffrn_measurement_device_type  ?
_diffrn_measurement_method       ?
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   ?
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                5965
_reflns_number_total             7902
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       ?
_computing_data_collection       ?
_computing_data_reduction        ?
_computing_molecular_graphics    
;
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  
;
SHELX, G.M. Sheldrick, Acta Cryst.
(2008). A64, 112-122
;
_computing_structure_solution    
;
SHELX, G.M. Sheldrick, Acta Cryst.
(2008). A64, 112-122
;
_refine_diff_density_max         5.180
_refine_diff_density_min         -2.401
_refine_diff_density_rms         0.344
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.119
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     457
_refine_ls_number_reflns         7902
_refine_ls_number_restraints     578
_refine_ls_R_factor_all          0.1407
_refine_ls_R_factor_gt           0.1202
_refine_ls_restrained_S_all      1.095
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
;
 w=1/[σ²(Fo²)+(0.1732P)²+116.6706P]
 where P=(Fo²+2Fc²)/3
;
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.3300
_refine_ls_wR_factor_ref         0.3512
_refine_special_details          
;
 ?
;
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
2. Restrained distances
 C33-C34
 1.55 with sigma of 0.005
 C35-C34
 1.55 with sigma of 0.005
 C14-C15
 1.55 with sigma of 0.005
 C16-C15
 1.55 with sigma of 0.005
3. Rigid bond restraints
 All non-hydrogen atoms
 with sigma for 1-2 distances of 0.005 and sigma for 1-3 distances of 0.005
4. Uiso/Uaniso restraints and constraints
C26 \\sim C38 \\sim C37 \\sim C36 \\sim C25 \\sim C24 \\sim C33 \\sim C34 \\sim
C35: within 1.7A with sigma of 0.005 and sigma for terminal atoms of 0.01
C4 \\sim C16 \\sim C15 \\sim C14 \\sim C3 \\sim C13 \\sim C12 \\sim C11 \\sim
C2: within 1.7A with sigma of 0.005 and sigma for terminal atoms of 0.01
All non-hydrogen atoms restrained to be isotropic: with sigma of 0.01 and sigma
for terminal atoms of 0.02
5.a Ternary CH refined with riding coordinates:
 C2(H2), C4(H4), C24(H24), C26(H26)
5.b Secondary CH2 refined with riding coordinates:
 C11(H11A,H11B), C12(H12A,H12B), C13(H13A,H13B), C14(H14A,H14B), C15(H15A,
 H15B), C16(H16A,H16B), C33(H33A,H33B), C34(H34A,H34B), C35(H35A,H35B),
 C36(H36A,H36B), C37(H37A,H37B), C38(H38A,H38B)
5.c Aromatic/amide H refined with riding coordinates:
 C6(H6), C7(H7), C8(H8), C9(H9), C10(H10), C18(H18), C19(H19), C20(H20),
 C21(H21), C22(H22), C28(H28), C29(H29), C30(H30), C31(H31), C32(H32), C44(H44),
  C43(H43), C42(H42), C41(H41), C40(H40)
5.d Fitted hexagon refined as free rotating group:
 C44(C43,C42,C41,C40,C39)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Au1 Au 0.33803(4) 0.81477(9) 0.03772(4) 0.0542(3) Uani 1 1 d . U . . .
Au2 Au 0.45591(4) 0.68377(9) 0.66048(5) 0.0558(3) Uani 1 1 d . U . . .
Cl1 Cl 0.2461(2) 0.8786(4) -0.0563(2) 0.0462(9) Uani 1 1 d . U . . .
Cl2 Cl 0.55322(19) 0.6277(4) 0.7523(2) 0.0460(9) Uani 1 1 d . U . . .
N1 N 0.4832(9) 0.7705(19) 0.1172(10) 0.058(3) Uani 1 1 d . U . . .
N2 N 0.4037(10) 0.7604(19) 0.1842(9) 0.058(3) Uani 1 1 d . U . . .
N3 N 0.3082(9) 0.7483(19) 0.5943(9) 0.056(3) Uani 1 1 d . U . . .
N4 N 0.3806(10) 0.744(2) 0.5181(9) 0.062(3) Uani 1 1 d . U . . .
C1 C 0.4169(10) 0.7718(16) 0.1206(10) 0.045(3) Uani 1 1 d . U . . .
C2 C 0.5451(13) 0.750(3) 0.1773(14) 0.075(2) Uani 1 1 d . U . . .
H2 H 0.5847 0.7970 0.1690 0.090 Uiso 1 1 calc R U . . .
C3 C 0.5318(15) 0.797(3) 0.2433(15) 0.078(2) Uani 1 1 d . U . . .
C4 C 0.4578(14) 0.755(3) 0.2509(13) 0.074(2) Uani 1 1 d . U . . .
H4 H 0.4610 0.6705 0.2693 0.089 Uiso 1 1 calc R U . . .
C5 C 0.4970(12) 0.775(2) 0.0487(13) 0.063(3) Uani 1 1 d . U . . .
C6 C 0.5387(14) 0.867(3) 0.0345(14) 0.072(4) Uani 1 1 d . U . . .
H6 H 0.5570 0.9282 0.0670 0.086 Uiso 1 1 calc R U . . .
C7 C 0.5527(15) 0.866(3) -0.0285(14) 0.078(5) Uani 1 1 d . U . . .
H7 H 0.5827 0.9268 -0.0378 0.093 Uiso 1 1 calc R U . . .
C8 C 0.5246(16) 0.781(3) -0.0791(17) 0.087(6) Uani 1 1 d . U . . .
H8 H 0.5321 0.7892 -0.1229 0.105 Uiso 1 1 calc R U . . .
C9 C 0.4851(19) 0.683(3) -0.0651(18) 0.093(6) Uani 1 1 d . U . . .
H9 H 0.4678 0.6219 -0.0979 0.111 Uiso 1 1 calc R U . . .
C10 C 0.4718(15) 0.680(3) 0.0031(14) 0.076(5) Uani 1 1 d . U . . .
H10 H 0.4468 0.6146 0.0156 0.091 Uiso 1 1 calc R U . . .
C11 C 0.5694(15) 0.618(3) 0.1932(14) 0.078(3) Uani 1 1 d . U . . .
H11A H 0.5294 0.5629 0.1877 0.093 Uiso 1 1 calc R U . . .
H11B H 0.5978 0.5910 0.1631 0.093 Uiso 1 1 calc R U . . .
C12 C 0.6123(15) 0.622(3) 0.2674(15) 0.080(3) Uani 1 1 d . U . . .
H12A H 0.6070 0.5453 0.2905 0.096 Uiso 1 1 calc R U . . .
H12B H 0.6618 0.6331 0.2696 0.096 Uiso 1 1 calc R U . . .
C13 C 0.5910(16) 0.710(3) 0.2963(15) 0.080(3) Uani 1 1 d . U . . .
H13A H 0.6310 0.7618 0.3187 0.096 Uiso 1 1 calc R U . . .
H13B H 0.5709 0.6782 0.3321 0.096 Uiso 1 1 calc R U . . .
C14 C 0.5248(14) 0.934(3) 0.2510(14) 0.081(3) Uani 1 1 d D U . . .
H14A H 0.5126 0.9711 0.2053 0.098 Uiso 1 1 calc R U . . .
H14B H 0.5700 0.9669 0.2766 0.098 Uiso 1 1 calc R U . . .
C15 C 0.4684(13) 0.970(2) 0.2889(14) 0.082(3) Uani 1 1 d D U . . .
H15A H 0.4896 1.0119 0.3324 0.099 Uiso 1 1 calc R U . . .
H15B H 0.4325 1.0232 0.2602 0.099 Uiso 1 1 calc R U . . .
C16 C 0.4374(16) 0.843(2) 0.3013(15) 0.079(3) Uani 1 1 d D U . . .
H16A H 0.4570 0.8160 0.3487 0.094 Uiso 1 1 calc R U . . .
H16B H 0.3865 0.8481 0.2923 0.094 Uiso 1 1 calc R U . . .
C17 C 0.3327(12) 0.743(2) 0.1866(11) 0.059(3) Uani 1 1 d . U . . .
C18 C 0.2841(13) 0.841(2) 0.1745(13) 0.066(4) Uani 1 1 d . U . . .
H18 H 0.2984 0.9201 0.1657 0.079 Uiso 1 1 calc R U . . .
C19 C 0.2172(14) 0.821(3) 0.1758(14) 0.069(4) Uani 1 1 d . U . . .
H19 H 0.1860 0.8874 0.1669 0.083 Uiso 1 1 calc R U . . .
C20 C 0.1919(14) 0.708(3) 0.1895(14) 0.074(5) Uani 1 1 d . U . . .
H20 H 0.1451 0.6963 0.1897 0.088 Uiso 1 1 calc R U . . .
C21 C 0.2406(13) 0.613(3) 0.2029(15) 0.074(5) Uani 1 1 d . U . . .
H21 H 0.2263 0.5358 0.2150 0.089 Uiso 1 1 calc R U . . .
C22 C 0.3112(13) 0.627(2) 0.1992(13) 0.066(4) Uani 1 1 d . U . . .
H22 H 0.3417 0.5594 0.2051 0.080 Uiso 1 1 calc R U . . .
C23 C 0.3710(10) 0.734(2) 0.5816(10) 0.050(3) Uani 1 1 d . U . . .
C24 C 0.2445(12) 0.772(3) 0.5392(12) 0.062(2) Uani 1 1 d . U . . .
H24 H 0.2173 0.6954 0.5268 0.075 Uiso 1 1 calc R U . . .
C25 C 0.2580(13) 0.830(2) 0.4758(13) 0.063(2) Uani 1 1 d . U . . .
C26 C 0.3205(12) 0.771(3) 0.4573(12) 0.063(2) Uani 1 1 d . U . . .
H26 H 0.3364 0.8244 0.4248 0.076 Uiso 1 1 calc R U . . .
C27 C 0.2999(11) 0.732(2) 0.6627(11) 0.055(3) Uani 1 1 d . U . . .
C28 C 0.2616(14) 0.634(3) 0.6761(14) 0.073(5) Uani 1 1 d . U . . .
H28 H 0.2389 0.5796 0.6414 0.087 Uiso 1 1 calc R U . . .
C29 C 0.2579(16) 0.620(3) 0.7471(14) 0.079(5) Uani 1 1 d . U . . .
H29 H 0.2308 0.5558 0.7573 0.095 Uiso 1 1 calc R U . . .
C30 C 0.2897(16) 0.691(3) 0.7961(15) 0.077(5) Uani 1 1 d . U . . .
H30 H 0.2897 0.6742 0.8417 0.093 Uiso 1 1 calc R U . . .
C31 C 0.3238(16) 0.792(3) 0.7802(15) 0.079(5) Uani 1 1 d . U . . .
H31 H 0.3397 0.8519 0.8141 0.095 Uiso 1 1 calc R U . . .
C32 C 0.3363(15) 0.810(3) 0.7130(13) 0.072(5) Uani 1 1 d . U . . .
H32 H 0.3670 0.8695 0.7046 0.086 Uiso 1 1 calc R U . . .
C33 C 0.1992(12) 0.8715(19) 0.5609(13) 0.066(2) Uani 1 1 d D U . . .
H33A H 0.1992 0.8604 0.6090 0.079 Uiso 1 1 calc R U . . .
H33B H 0.1509 0.8665 0.5324 0.079 Uiso 1 1 calc R U . . .
C34 C 0.2317(12) 0.9986(19) 0.5509(12) 0.070(3) Uani 1 1 d D U . . .
H34A H 0.2632 1.0281 0.5938 0.084 Uiso 1 1 calc R U . . .
H34B H 0.1954 1.0602 0.5334 0.084 Uiso 1 1 calc R U . . .
C35 C 0.2725(12) 0.967(2) 0.4965(11) 0.067(2) Uani 1 1 d D U . . .
H35A H 0.2567 1.0201 0.4561 0.080 Uiso 1 1 calc R U . . .
H35B H 0.3227 0.9805 0.5160 0.080 Uiso 1 1 calc R U . . .
C36 C 0.2005(13) 0.817(2) 0.4111(13) 0.062(3) Uani 1 1 d . U . . .
H36A H 0.2042 0.8799 0.3775 0.075 Uiso 1 1 calc R U . . .
H36B H 0.1546 0.8237 0.4204 0.075 Uiso 1 1 calc R U . . .
C37 C 0.2130(14) 0.672(3) 0.3816(14) 0.073(3) Uani 1 1 d . U . . .
H37A H 0.1818 0.6116 0.3939 0.087 Uiso 1 1 calc R U . . .
H37B H 0.2065 0.6710 0.3318 0.087 Uiso 1 1 calc R U . . .
C38 C 0.2848(13) 0.651(3) 0.4182(14) 0.070(3) Uani 1 1 d . U . . .
H38A H 0.3108 0.6242 0.3858 0.084 Uiso 1 1 calc R U . . .
H38B H 0.2870 0.5849 0.4516 0.084 Uiso 1 1 calc R U . . .
C44 C 0.4704(9) 0.6435(15) 0.4729(9) 0.081(5) Uani 1 1 d G U . . .
H44 H 0.4394 0.5792 0.4552 0.097 Uiso 1 1 calc R U . . .
C43 C 0.5381(10) 0.6431(18) 0.4639(11) 0.092(6) Uani 1 1 d G U . . .
H43 H 0.5525 0.5784 0.4401 0.110 Uiso 1 1 calc R U . . .
C42 C 0.5843(7) 0.739(2) 0.4904(11) 0.097(6) Uani 1 1 d G U . . .
H42 H 0.6296 0.7389 0.4844 0.116 Uiso 1 1 calc R U . . .
C41 C 0.5628(9) 0.8359(18) 0.5259(11) 0.088(5) Uani 1 1 d G U . . .
H41 H 0.5938 0.9002 0.5437 0.105 Uiso 1 1 calc R U . . .
C40 C 0.4951(9) 0.8363(15) 0.5349(9) 0.081(5) Uani 1 1 d G U . . .
H40 H 0.4807 0.9010 0.5587 0.097 Uiso 1 1 calc R U . . .
C39 C 0.4489(7) 0.7402(17) 0.5084(9) 0.065(4) Uani 1 1 d G U . . .


_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
Au1 Cl1 2.341(4) . ?
Au1 C1 2.002(19) . ?
Au2 Cl2 2.354(4) . ?
Au2 C23 2.042(19) . ?
N1 C1 1.32(2) . ?
N1 C2 1.48(3) . ?
N1 C5 1.47(3) . ?
N2 C1 1.37(2) . ?
N2 C4 1.47(3) . ?
N2 C17 1.42(3) . ?
N3 C23 1.33(2) . ?
N3 C24 1.45(3) . ?
N3 C27 1.43(3) . ?
N4 C23 1.34(3) . ?
N4 C26 1.48(3) . ?
N4 C39 1.41(2) . ?
C2 C3 1.50(4) . ?
C2 C11 1.51(4) . ?
C3 C4 1.57(4) . ?
C3 C13 1.64(4) . ?
C3 C14 1.49(4) . ?
C4 C16 1.52(4) . ?
C5 C6 1.37(4) . ?
C5 C10 1.38(4) . ?
C6 C7 1.36(4) . ?
C7 C8 1.37(4) . ?
C8 C9 1.39(4) . ?
C9 C10 1.45(4) . ?
C11 C12 1.50(4) . ?
C12 C13 1.24(4) . ?
C14 C15 1.550(5) . ?
C15 C16 1.549(5) . ?
C17 C18 1.41(3) . ?
C17 C22 1.37(4) . ?
C18 C19 1.34(3) . ?
C19 C20 1.37(4) . ?
C20 C21 1.38(4) . ?
C21 C22 1.42(3) . ?
C24 C25 1.50(3) . ?
C24 C33 1.53(3) . ?
C25 C26 1.52(3) . ?
C25 C35 1.55(3) . ?
C25 C36 1.48(3) . ?
C26 C38 1.58(4) . ?
C27 C28 1.36(4) . ?
C27 C32 1.36(3) . ?
C28 C29 1.45(4) . ?
C29 C30 1.27(4) . ?
C30 C31 1.36(4) . ?
C31 C32 1.44(4) . ?
C33 C34 1.550(5) . ?
C34 C35 1.551(5) . ?
C36 C37 1.72(3) . ?
C37 C38 1.42(4) . ?
C44 C43 1.3900 . ?
C44 C39 1.3900 . ?
C43 C42 1.3900 . ?
C42 C41 1.3900 . ?
C41 C40 1.3900 . ?
C40 C39 1.3900 . ?

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 Au1 Cl1 176.2(5) . . ?
C23 Au2 Cl2 179.3(6) . . ?
C1 N1 C2 124.6(19) . . ?
C1 N1 C5 118.5(18) . . ?
C5 N1 C2 116.5(18) . . ?
C1 N2 C4 125.1(18) . . ?
C1 N2 C17 118.2(18) . . ?
C17 N2 C4 116.4(18) . . ?
C23 N3 C24 122.2(18) . . ?
C23 N3 C27 120.8(18) . . ?
C27 N3 C24 116.9(17) . . ?
C23 N4 C26 121.0(18) . . ?
C23 N4 C39 120.5(18) . . ?
C39 N4 C26 118.3(17) . . ?
N1 C1 Au1 121.1(14) . . ?
N1 C1 N2 118.7(18) . . ?
N2 C1 Au1 119.6(14) . . ?
N1 C2 C3 111(2) . . ?
N1 C2 C11 117(2) . . ?
C3 C2 C11 105(2) . . ?
C2 C3 C4 112(2) . . ?
C2 C3 C13 97(2) . . ?
C4 C3 C13 107(2) . . ?
C14 C3 C2 118(3) . . ?
C14 C3 C4 99(2) . . ?
C14 C3 C13 124(2) . . ?
N2 C4 C3 112(2) . . ?
N2 C4 C16 109(2) . . ?
C16 C4 C3 107(2) . . ?
C6 C5 N1 119(2) . . ?
C6 C5 C10 123(2) . . ?
C10 C5 N1 118(2) . . ?
C7 C6 C5 118(3) . . ?
C6 C7 C8 123(3) . . ?
C7 C8 C9 120(3) . . ?
C8 C9 C10 117(3) . . ?
C5 C10 C9 119(3) . . ?
C12 C11 C2 104(3) . . ?
C13 C12 C11 108(3) . . ?
C12 C13 C3 114(3) . . ?
C3 C14 C15 114(2) . . ?
C16 C15 C14 102(2) . . ?
C4 C16 C15 105(2) . . ?
C18 C17 N2 121(2) . . ?
C22 C17 N2 119(2) . . ?
C22 C17 C18 120(2) . . ?
C19 C18 C17 120(2) . . ?
C18 C19 C20 124(3) . . ?
C19 C20 C21 116(2) . . ?
C20 C21 C22 123(3) . . ?
C17 C22 C21 117(2) . . ?
N3 C23 Au2 119.6(15) . . ?
N3 C23 N4 122.7(19) . . ?
N4 C23 Au2 117.7(14) . . ?
N3 C24 C25 113.8(19) . . ?
N3 C24 C33 111(2) . . ?
C25 C24 C33 101(2) . . ?
C24 C25 C26 111(2) . . ?
C24 C25 C35 104(2) . . ?
C26 C25 C35 111(2) . . ?
C36 C25 C24 116(2) . . ?
C36 C25 C26 103(2) . . ?
C36 C25 C35 112(2) . . ?
N4 C26 C25 113.8(19) . . ?
N4 C26 C38 114(2) . . ?
C25 C26 C38 100.6(19) . . ?
C28 C27 N3 120(2) . . ?
C32 C27 N3 117(2) . . ?
C32 C27 C28 123(2) . . ?
C27 C28 C29 117(3) . . ?
C30 C29 C28 123(3) . . ?
C29 C30 C31 118(3) . . ?
C30 C31 C32 123(3) . . ?
C27 C32 C31 115(3) . . ?
C24 C33 C34 107.2(18) . . ?
C33 C34 C35 101.9(17) . . ?
C25 C35 C34 107.6(19) . . ?
C25 C36 C37 104(2) . . ?
C38 C37 C36 101(2) . . ?
C37 C38 C26 112(2) . . ?
C43 C44 C39 120.0 . . ?
C44 C43 C42 120.0 . . ?
C43 C42 C41 120.0 . . ?
C40 C41 C42 120.0 . . ?
C41 C40 C39 120.0 . . ?
C44 C39 N4 121.7(15) . . ?
C40 C39 N4 118.3(15) . . ?
C40 C39 C44 120.0 . . ?

_database_code_depnum_ccdc_archive 'CCDC 973598'
#######################################################################
#
#                 Cambridge Crystallographic Data Centre
#                                CCDC 
# 
#######################################################################
# 
#  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.
#
#  This CIF is provided on the understanding that it is used for bona
#  fide research purposes only. It may contain copyright material
#  of the CCDC or of third parties, and may not be copied or further
#  disseminated in any form, whether machine-readable or not,
#  except for the purpose of generating routine backup copies
#  on your local computer system.
# 
#  For further information on the CCDC, data deposition and
#  data retrieval see:
#                         www.ccdc.cam.ac.uk
#
#  Bona fide researchers may freely download Mercury and enCIFer
#  from this site to visualise CIF-encoded structures and 
#  to carry out CIF format checking respectively.
#
data_tuyq0320
_audit_creation_date             2013-03-21
_audit_creation_method           
;
  Olex2 1.2
  (compiled Dec  5 2012 16:20:19, GUI svn.r4385)
;
_chemical_name_common            ?
_chemical_name_systematic        
;
 ? 
;
_chemical_formula_moiety         'C22 H24 B F3 N2'
_chemical_formula_sum            'C22 H24 B F3 N2'
_chemical_formula_weight         384.24
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 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'
F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
B B 0.0013 0.0007 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 1 21/n 1'
_space_group_name_Hall           '-P 2yn'
loop_
_space_group_symop_id
_space_group_symop_operation_xyz
1 'x, y, z'
2 '-x+1/2, y+1/2, -z+1/2'
3 '-x, -y, -z'
4 'x-1/2, -y-1/2, z-1/2'

_cell_length_a                   8.8224(2)
_cell_length_b                   14.8677(5)
_cell_length_c                   14.6800(6)
_cell_angle_alpha                90.00
_cell_angle_beta                 96.474(3)
_cell_angle_gamma                90.00
_cell_volume                     1913.28(11)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    3063
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      27.8070
_cell_measurement_theta_min      3.1550
_exptl_absorpt_coefficient_mu    0.098
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.89157
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.24 (release 03-12-2012 CrysAlis171 .NET)
(compiled Dec  3 2012,18:21:49)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            'clear light colourless'
_exptl_crystal_density_diffrn    1.334
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             808
_exptl_crystal_size_max          0.35
_exptl_crystal_size_mid          0.32
_exptl_crystal_size_min          0.22
_exptl_special_details           
;
 ? 
;
_diffrn_reflns_av_R_equivalents  0.0234
_diffrn_reflns_av_unetI/netI     0.0379
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            8341
_diffrn_reflns_theta_full        25.50
_diffrn_reflns_theta_max         26.37
_diffrn_reflns_theta_min         3.08
_diffrn_ambient_temperature      293(2)
_diffrn_detector_area_resol_mean 16.0733
_diffrn_measured_fraction_theta_full 0.9975
_diffrn_measured_fraction_theta_max 0.8955
_diffrn_measurement_details      
;
#__ type_ start__ end____ width___ exp.time_
  1 omega  -53.00   -7.40   1.2000   14.0000
omega____ theta____ kappa____ phi______ frames
    -      -19.3700   77.0000  150.0000 38

#__ type_ start__ end____ width___ exp.time_
  2 omega  -17.00   10.60   1.2000   14.0000
omega____ theta____ kappa____ phi______ frames
    -      -19.3700  -99.0000   90.0000 23

#__ type_ start__ end____ width___ exp.time_
  3 omega   -1.00   65.00   1.2000   14.0000
omega____ theta____ kappa____ phi______ frames
    -       22.6512  -99.0000    0.0000 55

#__ type_ start__ end____ width___ exp.time_
  4 omega  -29.00   95.80   1.2000   14.0000
omega____ theta____ kappa____ phi______ frames
    -       22.6512   19.0000  -60.0000 104
;
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, Eos'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_UB_11      0.0537733000
_diffrn_orient_matrix_UB_12      0.0092247000
_diffrn_orient_matrix_UB_13      0.0385003000
_diffrn_orient_matrix_UB_21      0.0155993000
_diffrn_orient_matrix_UB_22      -0.0466401000
_diffrn_orient_matrix_UB_23      0.0051439000
_diffrn_orient_matrix_UB_31      0.0584020000
_diffrn_orient_matrix_UB_32      0.0039665000
_diffrn_orient_matrix_UB_33      -0.0292574000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.7107
_diffrn_source                   'SuperNova (Mo) X-ray Source'
_diffrn_standards_decay_%        ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_number         ?
_reflns_number_gt                2937
_reflns_number_total             3903
_reflns_odcompleteness_completeness 99.75
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     26.32
_reflns_threshold_expression     >2sigma(I)
_computing_cell_refinement       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.24 (release 03-12-2012 CrysAlis171 .NET)
(compiled Dec  3 2012,18:21:49)
;
_computing_data_collection       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.24 (release 03-12-2012 CrysAlis171 .NET)
(compiled Dec  3 2012,18:21:49)
;
_computing_data_reduction        
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.24 (release 03-12-2012 CrysAlis171 .NET)
(compiled Dec  3 2012,18:21:49)
;
_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-97 (Sheldrick, 1990)'
_refine_diff_density_max         0.236
_refine_diff_density_min         -0.159
_refine_diff_density_rms         0.038
_refine_ls_extinction_coef       ?
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.063
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     253
_refine_ls_number_reflns         3903
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0655
_refine_ls_R_factor_gt           0.0467
_refine_ls_restrained_S_all      1.063
_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/[σ²(Fo²)+(0.0286P)²+0.7615P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0985
_refine_ls_wR_factor_ref         0.1089
_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. 
;
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  H22 of C22, H21 of C21, H20 of C20, H19 of C19, {H4A,H4B} of C4, {H3A,H3B}
  of C3, {H2A,H2B} of C2, H1 of C1, {H6A,H6B} of C6, {H7A,H7B} of C7, {H8A,H8B}
  of C8, H9 of C9, H12 of C12, H13 of C13, H14 of C14, H15 of C15, H16 of C16,
  H18 of C18
2.a Ternary CH refined with riding coordinates:
 C1(H1), C9(H9)
2.b Secondary CH2 refined with riding coordinates:
 C2(H2A,H2B), C3(H3A,H3B), C4(H4A,H4B), C6(H6A,H6B), C7(H7A,H7B), C8(H8A,H8B)
2.c Aromatic/amide H refined with riding coordinates:
 C12(H12), C13(H13), C14(H14), C15(H15), C16(H16), C18(H18), C19(H19),
 C20(H20), C21(H21), C22(H22)
;
_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
F1 F 0.65816(12) 0.40161(8) 0.59203(8) 0.0486(3) Uani 1 1 d . . .
F2 F 0.74668(12) 0.48980(8) 0.70990(8) 0.0515(3) Uani 1 1 d . . .
F3 F 0.66010(13) 0.34937(8) 0.73802(9) 0.0563(3) Uani 1 1 d . . .
N1 N 0.44500(15) 0.54229(10) 0.73420(10) 0.0316(3) Uani 1 1 d . . .
N2 N 0.34425(15) 0.43664(10) 0.63009(10) 0.0302(3) Uani 1 1 d . . .
C1 C 0.30719(19) 0.59802(12) 0.71783(13) 0.0331(4) Uani 1 1 d . . .
H1 H 0.2985 0.6345 0.7726 0.040 Uiso 1 1 calc R . .
C2 C 0.3016(2) 0.66074(13) 0.63475(15) 0.0430(5) Uani 1 1 d . . .
H2A H 0.3396 0.6309 0.5832 0.052 Uiso 1 1 calc R . .
H2B H 0.3610 0.7148 0.6494 0.052 Uiso 1 1 calc R . .
C3 C 0.1308(2) 0.68279(16) 0.61399(17) 0.0560(6) Uani 1 1 d . . .
H3A H 0.1096 0.7423 0.6365 0.067 Uiso 1 1 calc R . .
H3B H 0.1000 0.6809 0.5485 0.067 Uiso 1 1 calc R . .
C4 C 0.0453(2) 0.61104(14) 0.66327(15) 0.0444(5) Uani 1 1 d . . .
H4A H -0.0014 0.6376 0.7136 0.053 Uiso 1 1 calc R . .
H4B H -0.0340 0.5836 0.6211 0.053 Uiso 1 1 calc R . .
C5 C 0.16437(19) 0.54071(12) 0.69918(12) 0.0336(4) Uani 1 1 d . . .
C6 C 0.1230(2) 0.48411(15) 0.78073(14) 0.0474(5) Uani 1 1 d . . .
H6A H 0.2066 0.4841 0.8297 0.057 Uiso 1 1 calc R . .
H6B H 0.0332 0.5085 0.8044 0.057 Uiso 1 1 calc R . .
C7 C 0.0917(3) 0.38880(15) 0.74485(18) 0.0598(7) Uani 1 1 d . . .
H7A H 0.1768 0.3494 0.7644 0.072 Uiso 1 1 calc R . .
H7B H 0.0002 0.3646 0.7666 0.072 Uiso 1 1 calc R . .
C8 C 0.0714(2) 0.39856(14) 0.64160(17) 0.0519(6) Uani 1 1 d . . .
H8A H -0.0323 0.4160 0.6197 0.062 Uiso 1 1 calc R . .
H8B H 0.0954 0.3428 0.6121 0.062 Uiso 1 1 calc R . .
C9 C 0.18394(19) 0.47245(12) 0.62349(13) 0.0354(4) Uani 1 1 d . . .
H9 H 0.1554 0.4995 0.5631 0.043 Uiso 1 1 calc R . .
C10 C 0.46405(18) 0.46814(12) 0.68446(12) 0.0298(4) Uani 1 1 d . . .
C11 C 0.55028(18) 0.56520(12) 0.81306(12) 0.0320(4) Uani 1 1 d . . .
C12 C 0.6051(2) 0.65245(13) 0.82347(14) 0.0413(5) Uani 1 1 d . . .
H12 H 0.5774 0.6953 0.7786 0.050 Uiso 1 1 calc R . .
C13 C 0.7011(2) 0.67531(16) 0.90087(16) 0.0532(6) Uani 1 1 d . . .
H13 H 0.7389 0.7336 0.9077 0.064 Uiso 1 1 calc R . .
C14 C 0.7413(2) 0.61236(17) 0.96793(16) 0.0563(6) Uani 1 1 d . . .
H14 H 0.8059 0.6280 1.0200 0.068 Uiso 1 1 calc R . .
C15 C 0.6853(2) 0.52603(16) 0.95760(15) 0.0523(6) Uani 1 1 d . . .
H15 H 0.7128 0.4833 1.0027 0.063 Uiso 1 1 calc R . .
C16 C 0.5881(2) 0.50237(14) 0.88037(13) 0.0412(5) Uani 1 1 d . . .
H16 H 0.5489 0.4444 0.8742 0.049 Uiso 1 1 calc R . .
C17 C 0.35642(18) 0.35851(12) 0.57210(12) 0.0317(4) Uani 1 1 d . . .
C18 C 0.3851(2) 0.27464(13) 0.61022(14) 0.0410(5) Uani 1 1 d . . .
H18 H 0.4069 0.2682 0.6734 0.049 Uiso 1 1 calc R . .
C19 C 0.3811(2) 0.20004(14) 0.55361(17) 0.0535(6) Uani 1 1 d . . .
H19 H 0.4033 0.1435 0.5787 0.064 Uiso 1 1 calc R . .
C20 C 0.3444(2) 0.20901(16) 0.45998(17) 0.0551(6) Uani 1 1 d . . .
H20 H 0.3390 0.1585 0.4223 0.066 Uiso 1 1 calc R . .
C21 C 0.3158(2) 0.29280(16) 0.42295(15) 0.0497(6) Uani 1 1 d . . .
H21 H 0.2912 0.2989 0.3600 0.060 Uiso 1 1 calc R . .
C22 C 0.3234(2) 0.36838(14) 0.47836(13) 0.0381(4) Uani 1 1 d . . .
H22 H 0.3065 0.4252 0.4528 0.046 Uiso 1 1 calc R . .
B1 B 0.6403(2) 0.42415(15) 0.68200(15) 0.0360(5) 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
F1 B1 1.389(2) . ?
F2 B1 1.384(2) . ?
F3 B1 1.382(2) . ?
N1 C1 1.469(2) . ?
N1 C10 1.343(2) . ?
N1 C11 1.441(2) . ?
N2 C9 1.504(2) . ?
N2 C10 1.335(2) . ?
N2 C17 1.451(2) . ?
C1 H1 0.9800 . ?
C1 C2 1.532(3) . ?
C1 C5 1.520(2) . ?
C2 H2A 0.9700 . ?
C2 H2B 0.9700 . ?
C2 C3 1.538(3) . ?
C3 H3A 0.9700 . ?
C3 H3B 0.9700 . ?
C3 C4 1.534(3) . ?
C4 H4A 0.9700 . ?
C4 H4B 0.9700 . ?
C4 C5 1.533(3) . ?
C5 C6 1.541(3) . ?
C5 C9 1.529(2) . ?
C6 H6A 0.9700 . ?
C6 H6B 0.9700 . ?
C6 C7 1.526(3) . ?
C7 H7A 0.9700 . ?
C7 H7B 0.9700 . ?
C7 C8 1.513(3) . ?
C8 H8A 0.9700 . ?
C8 H8B 0.9700 . ?
C8 C9 1.524(3) . ?
C9 H9 0.9800 . ?
C10 B1 1.691(3) . ?
C11 C12 1.387(3) . ?
C11 C16 1.373(3) . ?
C12 H12 0.9300 . ?
C12 C13 1.381(3) . ?
C13 H13 0.9300 . ?
C13 C14 1.375(3) . ?
C14 H14 0.9300 . ?
C14 C15 1.377(3) . ?
C15 H15 0.9300 . ?
C15 C16 1.387(3) . ?
C16 H16 0.9300 . ?
C17 C18 1.379(3) . ?
C17 C22 1.382(3) . ?
C18 H18 0.9300 . ?
C18 C19 1.384(3) . ?
C19 H19 0.9300 . ?
C19 C20 1.383(3) . ?
C20 H20 0.9300 . ?
C20 C21 1.371(3) . ?
C21 H21 0.9300 . ?
C21 C22 1.384(3) . ?
C22 H22 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
C10 N1 C1 121.74(14) . . ?
C10 N1 C11 121.46(14) . . ?
C11 N1 C1 116.42(14) . . ?
C10 N2 C9 126.12(14) . . ?
C10 N2 C17 121.70(14) . . ?
C17 N2 C9 112.13(13) . . ?
N1 C1 H1 108.5 . . ?
N1 C1 C2 115.19(14) . . ?
N1 C1 C5 111.55(14) . . ?
C2 C1 H1 108.5 . . ?
C5 C1 H1 108.5 . . ?
C5 C1 C2 104.25(15) . . ?
C1 C2 H2A 111.1 . . ?
C1 C2 H2B 111.1 . . ?
C1 C2 C3 103.33(16) . . ?
H2A C2 H2B 109.1 . . ?
C3 C2 H2A 111.1 . . ?
C3 C2 H2B 111.1 . . ?
C2 C3 H3A 110.5 . . ?
C2 C3 H3B 110.5 . . ?
H3A C3 H3B 108.7 . . ?
C4 C3 C2 106.34(16) . . ?
C4 C3 H3A 110.5 . . ?
C4 C3 H3B 110.5 . . ?
C3 C4 H4A 110.5 . . ?
C3 C4 H4B 110.5 . . ?
H4A C4 H4B 108.6 . . ?
C5 C4 C3 106.35(15) . . ?
C5 C4 H4A 110.5 . . ?
C5 C4 H4B 110.5 . . ?
C1 C5 C4 101.63(15) . . ?
C1 C5 C6 115.51(16) . . ?
C1 C5 C9 110.11(14) . . ?
C4 C5 C6 115.23(15) . . ?
C9 C5 C4 109.39(15) . . ?
C9 C5 C6 104.97(16) . . ?
C5 C6 H6A 110.4 . . ?
C5 C6 H6B 110.4 . . ?
H6A C6 H6B 108.6 . . ?
C7 C6 C5 106.76(17) . . ?
C7 C6 H6A 110.4 . . ?
C7 C6 H6B 110.4 . . ?
C6 C7 H7A 110.8 . . ?
C6 C7 H7B 110.8 . . ?
H7A C7 H7B 108.9 . . ?
C8 C7 C6 104.66(18) . . ?
C8 C7 H7A 110.8 . . ?
C8 C7 H7B 110.8 . . ?
C7 C8 H8A 111.0 . . ?
C7 C8 H8B 111.0 . . ?
C7 C8 C9 103.76(17) . . ?
H8A C8 H8B 109.0 . . ?
C9 C8 H8A 111.0 . . ?
C9 C8 H8B 111.0 . . ?
N2 C9 C5 111.75(14) . . ?
N2 C9 C8 111.10(15) . . ?
N2 C9 H9 110.3 . . ?
C5 C9 H9 110.3 . . ?
C8 C9 C5 102.85(15) . . ?
C8 C9 H9 110.3 . . ?
N1 C10 B1 120.05(15) . . ?
N2 C10 N1 118.27(15) . . ?
N2 C10 B1 121.29(15) . . ?
C12 C11 N1 119.66(17) . . ?
C16 C11 N1 119.98(16) . . ?
C16 C11 C12 120.22(18) . . ?
C11 C12 H12 120.2 . . ?
C13 C12 C11 119.7(2) . . ?
C13 C12 H12 120.2 . . ?
C12 C13 H13 119.8 . . ?
C14 C13 C12 120.4(2) . . ?
C14 C13 H13 119.8 . . ?
C13 C14 H14 120.2 . . ?
C13 C14 C15 119.7(2) . . ?
C15 C14 H14 120.2 . . ?
C14 C15 H15 119.8 . . ?
C14 C15 C16 120.5(2) . . ?
C16 C15 H15 119.8 . . ?
C11 C16 C15 119.55(19) . . ?
C11 C16 H16 120.2 . . ?
C15 C16 H16 120.2 . . ?
C18 C17 N2 120.54(16) . . ?
C18 C17 C22 120.58(18) . . ?
C22 C17 N2 118.56(17) . . ?
C17 C18 H18 120.3 . . ?
C17 C18 C19 119.34(19) . . ?
C19 C18 H18 120.3 . . ?
C18 C19 H19 119.8 . . ?
C20 C19 C18 120.5(2) . . ?
C20 C19 H19 119.8 . . ?
C19 C20 H20 120.2 . . ?
C21 C20 C19 119.6(2) . . ?
C21 C20 H20 120.2 . . ?
C20 C21 H21 119.7 . . ?
C20 C21 C22 120.7(2) . . ?
C22 C21 H21 119.7 . . ?
C17 C22 C21 119.33(19) . . ?
C17 C22 H22 120.3 . . ?
C21 C22 H22 120.3 . . ?
F1 B1 C10 108.47(15) . . ?
F2 B1 F1 107.82(16) . . ?
F2 B1 C10 108.39(15) . . ?
F3 B1 F1 110.59(17) . . ?
F3 B1 F2 110.82(17) . . ?
F3 B1 C10 110.67(15) . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
N1 C1 C2 C3 160.26(16) . . . . ?
N1 C1 C5 C4 -167.59(15) . . . . ?
N1 C1 C5 C6 66.9(2) . . . . ?
N1 C1 C5 C9 -51.7(2) . . . . ?
N1 C10 B1 F1 -136.04(17) . . . . ?
N1 C10 B1 F2 -19.2(2) . . . . ?
N1 C10 B1 F3 102.48(19) . . . . ?
N1 C11 C12 C13 177.38(17) . . . . ?
N1 C11 C16 C15 -177.68(17) . . . . ?
N2 C10 B1 F1 36.6(2) . . . . ?
N2 C10 B1 F2 153.42(16) . . . . ?
N2 C10 B1 F3 -84.9(2) . . . . ?
N2 C17 C18 C19 173.61(17) . . . . ?
N2 C17 C22 C21 -172.01(16) . . . . ?
C1 N1 C10 N2 -11.5(2) . . . . ?
C1 N1 C10 B1 161.38(16) . . . . ?
C1 N1 C11 C12 -54.0(2) . . . . ?
C1 N1 C11 C16 121.81(18) . . . . ?
C1 C2 C3 C4 -17.6(2) . . . . ?
C1 C5 C6 C7 -131.46(17) . . . . ?
C1 C5 C9 N2 37.2(2) . . . . ?
C1 C5 C9 C8 156.44(15) . . . . ?
C2 C1 C5 C4 -42.67(17) . . . . ?
C2 C1 C5 C6 -168.15(16) . . . . ?
C2 C1 C5 C9 73.20(18) . . . . ?
C2 C3 C4 C5 -8.5(2) . . . . ?
C3 C4 C5 C1 31.2(2) . . . . ?
C3 C4 C5 C6 156.91(18) . . . . ?
C3 C4 C5 C9 -85.15(19) . . . . ?
C4 C5 C6 C7 110.38(19) . . . . ?
C4 C5 C9 N2 148.08(15) . . . . ?
C4 C5 C9 C8 -92.68(18) . . . . ?
C5 C1 C2 C3 37.70(19) . . . . ?
C5 C6 C7 C8 -15.6(2) . . . . ?
C6 C5 C9 N2 -87.74(17) . . . . ?
C6 C5 C9 C8 31.51(18) . . . . ?
C6 C7 C8 C9 35.5(2) . . . . ?
C7 C8 C9 N2 77.98(19) . . . . ?
C7 C8 C9 C5 -41.71(19) . . . . ?
C9 N2 C10 N1 -4.7(3) . . . . ?
C9 N2 C10 B1 -177.46(16) . . . . ?
C9 N2 C17 C18 -110.80(18) . . . . ?
C9 N2 C17 C22 62.7(2) . . . . ?
C9 C5 C6 C7 -10.0(2) . . . . ?
C10 N1 C1 C2 -77.8(2) . . . . ?
C10 N1 C1 C5 40.8(2) . . . . ?
C10 N1 C11 C12 133.02(18) . . . . ?
C10 N1 C11 C16 -51.2(2) . . . . ?
C10 N2 C9 C5 -10.0(2) . . . . ?
C10 N2 C9 C8 -124.20(19) . . . . ?
C10 N2 C17 C18 66.8(2) . . . . ?
C10 N2 C17 C22 -119.72(18) . . . . ?
C11 N1 C1 C2 109.19(18) . . . . ?
C11 N1 C1 C5 -132.23(16) . . . . ?
C11 N1 C10 N2 161.14(15) . . . . ?
C11 N1 C10 B1 -26.0(2) . . . . ?
C11 C12 C13 C14 -0.7(3) . . . . ?
C12 C11 C16 C15 -1.9(3) . . . . ?
C12 C13 C14 C15 0.1(3) . . . . ?
C13 C14 C15 C16 -0.4(3) . . . . ?
C14 C15 C16 C11 1.3(3) . . . . ?
C16 C11 C12 C13 1.6(3) . . . . ?
C17 N2 C9 C5 167.47(15) . . . . ?
C17 N2 C9 C8 53.2(2) . . . . ?
C17 N2 C10 N1 178.12(15) . . . . ?
C17 N2 C10 B1 5.3(2) . . . . ?
C17 C18 C19 C20 -1.9(3) . . . . ?
C18 C17 C22 C21 1.5(3) . . . . ?
C18 C19 C20 C21 1.8(3) . . . . ?
C19 C20 C21 C22 0.0(3) . . . . ?
C20 C21 C22 C17 -1.6(3) . . . . ?
C22 C17 C18 C19 0.2(3) . . . . ?

_database_code_depnum_ccdc_archive 'CCDC 973599'
#######################################################################
#
#                 Cambridge Crystallographic Data Centre
#                                CCDC 
# 
#######################################################################
# 
#  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.
#
#  This CIF is provided on the understanding that it is used for bona
#  fide research purposes only. It may contain copyright material
#  of the CCDC or of third parties, and may not be copied or further
#  disseminated in any form, whether machine-readable or not,
#  except for the purpose of generating routine backup copies
#  on your local computer system.
# 
#  For further information on the CCDC, data deposition and
#  data retrieval see:
#                         www.ccdc.cam.ac.uk
#
#  Bona fide researchers may freely download Mercury and enCIFer
#  from this site to visualise CIF-encoded structures and 
#  to carry out CIF format checking respectively.
#
data_yangbm0909
_audit_creation_date             2013-09-13
_audit_creation_method           
;
  Olex2 1.2
  (compiled Apr 23 2013 17:54:37, GUI svn.r4466)
;
_chemical_name_common            ?
_chemical_name_systematic        
;
 ?
;
_chemical_formula_moiety         'C44 H48 Cu N4, Cl2 Cu, C4 H8 O'
_chemical_formula_sum            'C48 H56 Cl2 Cu2 N4 O'
_chemical_formula_weight         902.94
_chemical_absolute_configuration ?
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 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'
Cu Cu 0.3201 1.2651 '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'

_space_group_crystal_system      orthorhombic
_space_group_IT_number           33
_space_group_name_H-M_alt        'P n a 21'
_space_group_name_Hall           'P 2c -2n'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, z+1/2'
'-x+1/2, y+1/2, z+1/2'
'x+1/2, -y+1/2, z'

_cell_length_a                   22.4845(5)
_cell_length_b                   15.3897(5)
_cell_length_c                   12.7631(3)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     4416.4(2)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    5442
_cell_measurement_temperature    150.00(10)
_cell_measurement_theta_max      28.2640
_cell_measurement_theta_min      3.6320
_exptl_absorpt_coefficient_mu    1.124
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.50497
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET)
(compiled Feb  1 2013,16:14:44)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            'clear light colourless'
_exptl_crystal_density_diffrn    1.358
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             1888
_exptl_crystal_size_max          0.33
_exptl_crystal_size_mid          0.3
_exptl_crystal_size_min          0.25
_exptl_special_details           
;
 ?
;
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0289
_diffrn_reflns_av_unetI/netI     0.0389
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       27
_diffrn_reflns_limit_h_min       -27
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       8
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            12313
_diffrn_reflns_point_group_measured_fraction_full 0.737
_diffrn_reflns_point_group_measured_fraction_max 0.733
_diffrn_reflns_theta_full        25.500
_diffrn_reflns_theta_max         26.020
_diffrn_reflns_theta_min         3.023
_diffrn_ambient_temperature      150.00(10)
_diffrn_detector_area_resol_mean 16.0733
_diffrn_measured_fraction_theta_full 0.9972
_diffrn_measured_fraction_theta_max 0.6418
_diffrn_measurement_details      
;
#__ type_ start__ end____ width___ exp.time_
  1 omega -100.00  -62.00   1.0000   10.0000
omega____ theta____ kappa____ phi______ frames
    -      -19.5262  178.0000   60.0000 38

#__ type_ start__ end____ width___ exp.time_
  2 omega  -19.00   29.00   1.0000   10.0000
omega____ theta____ kappa____ phi______ frames
    -       22.8075  -99.0000   90.0000 48

#__ type_ start__ end____ width___ exp.time_
  3 omega  -48.00   42.00   1.0000   10.0000
omega____ theta____ kappa____ phi______ frames
    -       22.8075  -77.0000  -60.0000 90
;
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, Eos'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_UB_11      0.0004266000
_diffrn_orient_matrix_UB_12      0.0384386000
_diffrn_orient_matrix_UB_13      0.0306848000
_diffrn_orient_matrix_UB_21      0.0293479000
_diffrn_orient_matrix_UB_22      -0.0097863000
_diffrn_orient_matrix_UB_23      0.0166201000
_diffrn_orient_matrix_UB_31      0.0115426000
_diffrn_orient_matrix_UB_32      0.0234458000
_diffrn_orient_matrix_UB_33      -0.0432877000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.7107
_diffrn_source                   'SuperNova (Mo) X-ray Source'
_reflns_Friedel_coverage         0.402
_reflns_Friedel_fraction_full    0.449
_reflns_Friedel_fraction_max     0.441
_reflns_number_gt                5718
_reflns_number_total             6372
_reflns_odcompleteness_completeness 99.72
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     26.32
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET)
(compiled Feb  1 2013,16:14:44)
;
_computing_data_collection       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET)
(compiled Feb  1 2013,16:14:44)
;
_computing_data_reduction        
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET)
(compiled Feb  1 2013,16:14:44)
;
_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    'SUPERFLIP, J. Appl. Cryst. (2007) 40, 786-790'
_refine_diff_density_max         0.378
_refine_diff_density_min         -0.583
_refine_diff_density_rms         0.059
_refine_ls_abs_structure_details 
;
 Flack x determined using 1550 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons and Flack (2004), Acta Cryst. A60, s61).
;
_refine_ls_abs_structure_Flack   0.017(10)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.059
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     523
_refine_ls_number_reflns         6372
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0457
_refine_ls_R_factor_gt           0.0385
_refine_ls_restrained_S_all      1.059
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
;
 w=1/[σ²(Fo²)+(0.0565P)²+0.4435P]
 where P=(Fo²+2Fc²)/3
;
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0964
_refine_ls_wR_factor_ref         0.1018
_refine_special_details          
;
 ?
;
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All C(H,H,H,H) groups
2. Others
 Fixed Sof: H45A(0.5) H45B(0.5) H45C(0.5) H45D(0.5) H47A(0.5) H47B(0.5)
 H47C(0.5) H47D(0.5) C1A(0.5) H1AA(0.5) H1AB(0.5) C1B(0.5) H1BA(0.5) H1BB(0.5)
3.a Ternary CH refined with riding coordinates:
 C7(H7), C15(H15), C29(H29), C37(H37)
3.b Secondary CH2 refined with riding coordinates:
 C8(H8A,H8B), C9(H9A,H9B), C10(H10A,H10B), C12(H12A,H12B), C13(H13A,H13B),
 C14(H14A,H14B), C30(H30A,H30B), C31(H31A,H31B), C32(H32A,H32B), C34(H34A,H34B),
  C35(H35A,H35B), C36(H36A,H36B), C45(H45A,H45B), C45(H45C,H45D), C47(H47A,
 H47B), C47(H47C,H47D), C48(H48A,H48B), C1A(H1AA,H1AB), C1B(H1BA,H1BB)
3.c Aromatic/amide H refined with riding coordinates:
 C1(H1), C2(H2), C3(H3), C4(H4), C5(H5), C17(H17), C18(H18), C19(H19),
 C20(H20), C21(H21), C23(H23), C24(H24), C25(H25), C26(H26), C27(H27), C40(H40),
  C41(H41), C42(H42), C43(H43), C44(H44)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     iterative
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Cu1 Cu 0.59209(2) 0.69465(3) 0.58889(5) 0.02634(14) Uani 1 1 d . . . . .
Cu2 Cu 0.36434(3) 0.83686(5) 0.29678(6) 0.0485(2) Uani 1 1 d . . . . .
Cl1 Cl 0.36273(7) 0.97202(10) 0.31835(14) 0.0609(5) Uani 1 1 d . . . . .
Cl2 Cl 0.36639(8) 0.70119(10) 0.27998(16) 0.0647(5) Uani 1 1 d . . . . .
O1 O 0.29648(17) 0.4295(3) 0.5528(4) 0.0670(13) Uani 1 1 d . . . . .
N1 N 0.61303(15) 0.5144(2) 0.5546(3) 0.0282(9) Uani 1 1 d . . . . .
N2 N 0.69839(15) 0.5970(2) 0.5667(3) 0.0295(9) Uani 1 1 d . . . . .
N3 N 0.53507(16) 0.8454(2) 0.5128(3) 0.0257(8) Uani 1 1 d . . . . .
N4 N 0.52365(17) 0.8256(2) 0.6903(3) 0.0256(8) Uani 1 1 d . . . . .
C1 C 0.5165(2) 0.5671(3) 0.4945(5) 0.0385(13) Uani 1 1 d . . . . .
H1 H 0.5356 0.5967 0.4407 0.046 Uiso 1 1 calc R U . . .
C2 C 0.4555(2) 0.5753(3) 0.5068(5) 0.0472(15) Uani 1 1 d . . . . .
H2 H 0.4336 0.6113 0.4627 0.057 Uiso 1 1 calc R U . . .
C3 C 0.4276(2) 0.5289(3) 0.5860(7) 0.0560(17) Uani 1 1 d . . . . .
H3 H 0.3867 0.5341 0.5950 0.067 Uiso 1 1 calc R U . . .
C4 C 0.4594(2) 0.4757(3) 0.6510(6) 0.0481(15) Uani 1 1 d . . . . .
H4 H 0.4398 0.4446 0.7031 0.058 Uiso 1 1 calc R U . . .
C5 C 0.5211(2) 0.4675(3) 0.6401(5) 0.0413(13) Uani 1 1 d . . . . .
H5 H 0.5428 0.4312 0.6839 0.050 Uiso 1 1 calc R U . . .
C6 C 0.54897(18) 0.5152(3) 0.5619(4) 0.0312(11) Uani 1 1 d . . . . .
C7 C 0.64468(18) 0.4306(3) 0.5386(4) 0.0314(11) Uani 1 1 d . . . . .
H7 H 0.6488 0.3984 0.6045 0.038 Uiso 1 1 calc R U . . .
C8 C 0.6144(2) 0.3756(3) 0.4546(5) 0.0459(15) Uani 1 1 d . . . . .
H8A H 0.6242 0.3147 0.4638 0.055 Uiso 1 1 calc R U . . .
H8B H 0.5716 0.3821 0.4585 0.055 Uiso 1 1 calc R U . . .
C9 C 0.6375(3) 0.4085(6) 0.3500(6) 0.074(2) Uani 1 1 d . . . . .
H9A H 0.6067 0.4401 0.3130 0.089 Uiso 1 1 calc R U . . .
H9B H 0.6505 0.3603 0.3066 0.089 Uiso 1 1 calc R U . . .
C10 C 0.6897(2) 0.4683(4) 0.3752(4) 0.0432(13) Uani 1 1 d . . . . .
H10A H 0.6784 0.5287 0.3658 0.052 Uiso 1 1 calc R U . . .
H10B H 0.7232 0.4557 0.3300 0.052 Uiso 1 1 calc R U . . .
C11 C 0.7055(2) 0.4504(3) 0.4898(4) 0.0327(11) Uani 1 1 d . . . . .
C12 C 0.7489(2) 0.3745(4) 0.5053(5) 0.0464(14) Uani 1 1 d . . . . .
H12A H 0.7809 0.3772 0.4545 0.056 Uiso 1 1 calc R U . . .
H12B H 0.7285 0.3193 0.4977 0.056 Uiso 1 1 calc R U . . .
C13 C 0.7730(2) 0.3854(3) 0.6173(5) 0.0457(14) Uani 1 1 d . . . . .
H13A H 0.8153 0.3731 0.6194 0.055 Uiso 1 1 calc R U . . .
H13B H 0.7528 0.3461 0.6649 0.055 Uiso 1 1 calc R U . . .
C14 C 0.7610(2) 0.4808(3) 0.6485(5) 0.0410(13) Uani 1 1 d . . . . .
H14A H 0.7318 0.4841 0.7042 0.049 Uiso 1 1 calc R U . . .
H14B H 0.7973 0.5090 0.6716 0.049 Uiso 1 1 calc R U . . .
C15 C 0.73740(19) 0.5228(3) 0.5475(4) 0.0306(11) Uani 1 1 d . . . . .
H15 H 0.7712 0.5421 0.5051 0.037 Uiso 1 1 calc R U . . .
C16 C 0.72400(17) 0.6811(3) 0.5885(5) 0.0289(9) Uani 1 1 d . . . . .
C17 C 0.7637(2) 0.7179(3) 0.5167(4) 0.0338(11) Uani 1 1 d . . . . .
H17 H 0.7762 0.6868 0.4582 0.041 Uiso 1 1 calc R U . . .
C18 C 0.7840(2) 0.8019(3) 0.5345(5) 0.0404(13) Uani 1 1 d . . . . .
H18 H 0.8106 0.8271 0.4876 0.048 Uiso 1 1 calc R U . . .
C19 C 0.7655(2) 0.8480(3) 0.6199(5) 0.0459(15) Uani 1 1 d . . . . .
H19 H 0.7789 0.9046 0.6302 0.055 Uiso 1 1 calc R U . . .
C20 C 0.7264(2) 0.8102(3) 0.6919(5) 0.0428(13) Uani 1 1 d . . . . .
H20 H 0.7138 0.8416 0.7501 0.051 Uiso 1 1 calc R U . . .
C21 C 0.7064(2) 0.7260(3) 0.6766(4) 0.0349(11) Uani 1 1 d . . . . .
H21 H 0.6813 0.7001 0.7253 0.042 Uiso 1 1 calc R U . . .
C22 C 0.63875(17) 0.5929(3) 0.5688(4) 0.0285(10) Uani 1 1 d . . . . .
C23 C 0.6229(2) 0.8080(3) 0.4100(4) 0.0330(11) Uani 1 1 d . . . . .
H23 H 0.6469 0.8283 0.4642 0.040 Uiso 1 1 calc R U . . .
C24 C 0.6482(2) 0.7705(4) 0.3212(4) 0.0418(13) Uani 1 1 d . . . . .
H24 H 0.6893 0.7644 0.3165 0.050 Uiso 1 1 calc R U . . .
C25 C 0.6122(3) 0.7425(4) 0.2402(4) 0.0399(13) Uani 1 1 d . . . . .
H25 H 0.6292 0.7172 0.1812 0.048 Uiso 1 1 calc R U . . .
C26 C 0.5516(2) 0.7516(3) 0.2462(4) 0.0362(11) Uani 1 1 d . . . . .
H26 H 0.5277 0.7333 0.1910 0.043 Uiso 1 1 calc R U . . .
C27 C 0.5258(2) 0.7884(3) 0.3355(4) 0.0319(11) Uani 1 1 d . . . . .
H27 H 0.4848 0.7949 0.3399 0.038 Uiso 1 1 calc R U . . .
C28 C 0.5616(2) 0.8146(3) 0.4165(4) 0.0270(10) Uani 1 1 d . . . . .
C29 C 0.5039(2) 0.9290(3) 0.5150(4) 0.0305(10) Uani 1 1 d . . . . .
H29 H 0.4836 0.9379 0.4479 0.037 Uiso 1 1 calc R U . . .
C30 C 0.5459(2) 1.0063(3) 0.5362(5) 0.0390(12) Uani 1 1 d . . . . .
H30A H 0.5775 0.9900 0.5841 0.047 Uiso 1 1 calc R U . . .
H30B H 0.5635 1.0274 0.4716 0.047 Uiso 1 1 calc R U . . .
C31 C 0.5053(2) 1.0754(3) 0.5853(5) 0.0429(12) Uani 1 1 d . . . . .
H31A H 0.5001 1.1239 0.5377 0.051 Uiso 1 1 calc R U . . .
H31B H 0.5223 1.0968 0.6502 0.051 Uiso 1 1 calc R U . . .
C32 C 0.4453(2) 1.0304(3) 0.6063(5) 0.0405(13) Uani 1 1 d . . . . .
H32A H 0.4298 1.0468 0.6744 0.049 Uiso 1 1 calc R U . . .
H32B H 0.4164 1.0460 0.5530 0.049 Uiso 1 1 calc R U . . .
C33 C 0.45887(18) 0.9326(3) 0.6026(4) 0.0302(10) Uani 1 1 d . . . . .
C34 C 0.40404(19) 0.8731(3) 0.5866(5) 0.0374(10) Uani 1 1 d . . . . .
H34A H 0.3698 0.9074 0.5661 0.045 Uiso 1 1 calc R U . . .
H34B H 0.4119 0.8308 0.5321 0.045 Uiso 1 1 calc R U . . .
C35 C 0.3920(2) 0.8272(4) 0.6910(5) 0.0412(13) Uani 1 1 d . . . . .
H35A H 0.3502 0.8304 0.7093 0.049 Uiso 1 1 calc R U . . .
H35B H 0.4038 0.7666 0.6876 0.049 Uiso 1 1 calc R U . . .
C36 C 0.42992(19) 0.8765(4) 0.7707(4) 0.0378(12) Uani 1 1 d . . . . .
H36A H 0.4091 0.9274 0.7966 0.045 Uiso 1 1 calc R U . . .
H36B H 0.4405 0.8396 0.8294 0.045 Uiso 1 1 calc R U . . .
C37 C 0.4847(2) 0.9023(3) 0.7083(4) 0.0298(10) Uani 1 1 d . . . . .
H37 H 0.5065 0.9493 0.7431 0.036 Uiso 1 1 calc R U . . .
C38 C 0.54582(17) 0.7986(3) 0.5993(4) 0.0262(9) Uani 1 1 d . . . . .
C39 C 0.54119(18) 0.7750(3) 0.7806(4) 0.0254(9) Uani 1 1 d . . . . .
C40 C 0.5750(2) 0.8130(3) 0.8583(4) 0.0339(11) Uani 1 1 d . . . . .
H40 H 0.5837 0.8720 0.8551 0.041 Uiso 1 1 calc R U . . .
C41 C 0.5958(2) 0.7635(4) 0.9406(5) 0.0387(13) Uani 1 1 d . . . . .
H41 H 0.6186 0.7893 0.9927 0.046 Uiso 1 1 calc R U . . .
C42 C 0.5827(2) 0.6756(4) 0.9459(5) 0.0411(13) Uani 1 1 d . . . . .
H42 H 0.5975 0.6420 1.0006 0.049 Uiso 1 1 calc R U . . .
C43 C 0.5475(2) 0.6381(3) 0.8694(4) 0.0386(12) Uani 1 1 d . . . . .
H43 H 0.5379 0.5794 0.8735 0.046 Uiso 1 1 calc R U . . .
C44 C 0.5264(2) 0.6879(3) 0.7861(4) 0.0331(11) Uani 1 1 d . . . . .
H44 H 0.5027 0.6628 0.7347 0.040 Uiso 1 1 calc R U . . .
C45 C 0.2787(3) 0.4451(6) 0.4479(7) 0.081(2) Uani 1 1 d . . . . .
H45A H 0.2942 0.4001 0.4023 0.098 Uiso 0.5 1 calc R U P A 1
H45B H 0.2939 0.5007 0.4242 0.098 Uiso 0.5 1 calc R U P A 1
H45C H 0.3086 0.4245 0.3991 0.098 Uiso 0.5 1 calc R U P A 2
H45D H 0.2722 0.5066 0.4360 0.098 Uiso 0.5 1 calc R U P A 2
C47 C 0.1968(3) 0.3899(6) 0.5390(7) 0.085(3) Uani 1 1 d . . . . .
H47A H 0.1651 0.4175 0.5782 0.102 Uiso 0.5 1 calc R U P B 1
H47B H 0.1834 0.3329 0.5164 0.102 Uiso 0.5 1 calc R U P B 1
H47C H 0.1713 0.3396 0.5478 0.102 Uiso 0.5 1 calc R U P B 2
H47D H 0.1746 0.4420 0.5560 0.102 Uiso 0.5 1 calc R U P B 2
C48 C 0.2521(3) 0.3824(4) 0.6049(7) 0.068(2) Uani 1 1 d . . . . .
H48A H 0.2452 0.4063 0.6741 0.082 Uiso 1 1 calc R U . . .
H48B H 0.2637 0.3220 0.6121 0.082 Uiso 1 1 calc R U . . .
C1A C 0.2145(7) 0.4452(12) 0.4451(17) 0.068(5) Uani 0.5 1 d . . P C 1
H1AA H 0.1999 0.4199 0.3804 0.082 Uiso 0.5 1 calc R U P C 1
H1AB H 0.1990 0.5038 0.4517 0.082 Uiso 0.5 1 calc R U P C 1
C1B C 0.2205(9) 0.3940(12) 0.4353(17) 0.073(5) Uani 0.5 1 d . . P C 2
H1BA H 0.1934 0.4239 0.3885 0.087 Uiso 0.5 1 calc R U P C 2
H1BB H 0.2282 0.3362 0.4080 0.087 Uiso 0.5 1 calc R U P C 2


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Cu1 C22 1.902(4) . ?
Cu1 C38 1.913(4) . ?
Cu2 Cl1 2.0986(17) . ?
Cu2 Cl2 2.0993(17) . ?
O1 C45 1.417(10) . ?
O1 C48 1.402(8) . ?
N1 C6 1.443(5) . ?
N1 C7 1.488(5) . ?
N1 C22 1.352(5) . ?
N2 C15 1.461(5) . ?
N2 C16 1.445(5) . ?
N2 C22 1.343(5) . ?
N3 C28 1.446(6) . ?
N3 C29 1.464(5) . ?
N3 C38 1.341(6) . ?
N4 C37 1.487(5) . ?
N4 C38 1.330(6) . ?
N4 C39 1.446(6) . ?
C1 H1 0.9300 . ?
C1 C2 1.386(7) . ?
C1 C6 1.383(7) . ?
C2 H2 0.9300 . ?
C2 C3 1.387(10) . ?
C3 H3 0.9300 . ?
C3 C4 1.368(9) . ?
C4 H4 0.9300 . ?
C4 C5 1.400(7) . ?
C5 H5 0.9300 . ?
C5 C6 1.387(7) . ?
C7 H7 0.9800 . ?
C7 C8 1.526(8) . ?
C7 C11 1.534(7) . ?
C8 H8A 0.9700 . ?
C8 H8B 0.9700 . ?
C8 C9 1.521(10) . ?
C9 H9A 0.9700 . ?
C9 H9B 0.9700 . ?
C9 C10 1.525(9) . ?
C10 H10A 0.9700 . ?
C10 H10B 0.9700 . ?
C10 C11 1.531(7) . ?
C11 C12 1.535(6) . ?
C11 C15 1.515(7) . ?
C12 H12A 0.9700 . ?
C12 H12B 0.9700 . ?
C12 C13 1.539(9) . ?
C13 H13A 0.9700 . ?
C13 H13B 0.9700 . ?
C13 C14 1.544(7) . ?
C14 H14A 0.9700 . ?
C14 H14B 0.9700 . ?
C14 C15 1.538(7) . ?
C15 H15 0.9800 . ?
C16 C17 1.399(7) . ?
C16 C21 1.378(8) . ?
C17 H17 0.9300 . ?
C17 C18 1.390(7) . ?
C18 H18 0.9300 . ?
C18 C19 1.365(8) . ?
C19 H19 0.9300 . ?
C19 C20 1.399(8) . ?
C20 H20 0.9300 . ?
C20 C21 1.385(7) . ?
C21 H21 0.9300 . ?
C23 H23 0.9300 . ?
C23 C24 1.393(7) . ?
C23 C28 1.385(7) . ?
C24 H24 0.9300 . ?
C24 C25 1.383(8) . ?
C25 H25 0.9300 . ?
C25 C26 1.372(8) . ?
C26 H26 0.9300 . ?
C26 C27 1.398(7) . ?
C27 H27 0.9300 . ?
C27 C28 1.371(7) . ?
C29 H29 0.9800 . ?
C29 C30 1.543(7) . ?
C29 C33 1.510(7) . ?
C30 H30A 0.9700 . ?
C30 H30B 0.9700 . ?
C30 C31 1.535(7) . ?
C31 H31A 0.9700 . ?
C31 H31B 0.9700 . ?
C31 C32 1.540(7) . ?
C32 H32A 0.9700 . ?
C32 H32B 0.9700 . ?
C32 C33 1.536(6) . ?
C33 C34 1.549(6) . ?
C33 C37 1.541(7) . ?
C34 H34A 0.9700 . ?
C34 H34B 0.9700 . ?
C34 C35 1.532(9) . ?
C35 H35A 0.9700 . ?
C35 H35B 0.9700 . ?
C35 C36 1.528(7) . ?
C36 H36A 0.9700 . ?
C36 H36B 0.9700 . ?
C36 C37 1.520(7) . ?
C37 H37 0.9800 . ?
C39 C40 1.379(7) . ?
C39 C44 1.382(6) . ?
C40 H40 0.9300 . ?
C40 C41 1.379(7) . ?
C41 H41 0.9300 . ?
C41 C42 1.386(8) . ?
C42 H42 0.9300 . ?
C42 C43 1.384(8) . ?
C43 H43 0.9300 . ?
C43 C44 1.394(7) . ?
C44 H44 0.9300 . ?
C45 H45A 0.9700 . ?
C45 H45B 0.9700 . ?
C45 H45C 0.9700 . ?
C45 H45D 0.9700 . ?
C45 C1A 1.444(18) . ?
C45 C1B 1.53(2) . ?
C47 H47A 0.9700 . ?
C47 H47B 0.9700 . ?
C47 H47C 0.9700 . ?
C47 H47D 0.9700 . ?
C47 C48 1.505(9) . ?
C47 C1A 1.52(2) . ?
C47 C1B 1.43(2) . ?
C48 H48A 0.9700 . ?
C48 H48B 0.9700 . ?
C1A H1AA 0.9700 . ?
C1A H1AB 0.9700 . ?
C1B H1BA 0.9700 . ?
C1B H1BB 0.9700 . ?

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
C22 Cu1 C38 176.2(2) . . ?
Cl1 Cu2 Cl2 178.30(9) . . ?
C48 O1 C45 109.5(5) . . ?
C6 N1 C7 119.6(3) . . ?
C22 N1 C6 114.2(3) . . ?
C22 N1 C7 126.1(3) . . ?
C16 N2 C15 119.6(3) . . ?
C22 N2 C15 124.5(4) . . ?
C22 N2 C16 115.8(3) . . ?
C28 N3 C29 120.1(4) . . ?
C38 N3 C28 116.7(3) . . ?
C38 N3 C29 122.8(4) . . ?
C38 N4 C37 127.1(4) . . ?
C38 N4 C39 115.2(4) . . ?
C39 N4 C37 117.7(4) . . ?
C2 C1 H1 119.8 . . ?
C6 C1 H1 119.8 . . ?
C6 C1 C2 120.4(6) . . ?
C1 C2 H2 120.6 . . ?
C1 C2 C3 118.9(5) . . ?
C3 C2 H2 120.6 . . ?
C2 C3 H3 119.6 . . ?
C4 C3 C2 120.9(5) . . ?
C4 C3 H3 119.6 . . ?
C3 C4 H4 119.6 . . ?
C3 C4 C5 120.8(6) . . ?
C5 C4 H4 119.6 . . ?
C4 C5 H5 120.9 . . ?
C6 C5 C4 118.1(5) . . ?
C6 C5 H5 120.9 . . ?
C1 C6 N1 119.5(4) . . ?
C1 C6 C5 120.9(4) . . ?
C5 C6 N1 119.5(4) . . ?
N1 C7 H7 111.4 . . ?
N1 C7 C8 111.4(4) . . ?
N1 C7 C11 108.0(4) . . ?
C8 C7 H7 111.4 . . ?
C8 C7 C11 102.9(4) . . ?
C11 C7 H7 111.4 . . ?
C7 C8 H8A 110.5 . . ?
C7 C8 H8B 110.5 . . ?
H8A C8 H8B 108.7 . . ?
C9 C8 C7 106.2(4) . . ?
C9 C8 H8A 110.5 . . ?
C9 C8 H8B 110.5 . . ?
C8 C9 H9A 110.5 . . ?
C8 C9 H9B 110.5 . . ?
C8 C9 C10 106.2(5) . . ?
H9A C9 H9B 108.7 . . ?
C10 C9 H9A 110.5 . . ?
C10 C9 H9B 110.5 . . ?
C9 C10 H10A 110.6 . . ?
C9 C10 H10B 110.6 . . ?
C9 C10 C11 105.8(5) . . ?
H10A C10 H10B 108.7 . . ?
C11 C10 H10A 110.6 . . ?
C11 C10 H10B 110.6 . . ?
C7 C11 C12 111.3(4) . . ?
C10 C11 C7 102.5(4) . . ?
C10 C11 C12 114.0(4) . . ?
C15 C11 C7 111.8(4) . . ?
C15 C11 C10 116.2(4) . . ?
C15 C11 C12 101.4(4) . . ?
C11 C12 H12A 110.7 . . ?
C11 C12 H12B 110.7 . . ?
C11 C12 C13 105.0(5) . . ?
H12A C12 H12B 108.8 . . ?
C13 C12 H12A 110.7 . . ?
C13 C12 H12B 110.7 . . ?
C12 C13 H13A 110.4 . . ?
C12 C13 H13B 110.4 . . ?
C12 C13 C14 106.4(4) . . ?
H13A C13 H13B 108.6 . . ?
C14 C13 H13A 110.4 . . ?
C14 C13 H13B 110.4 . . ?
C13 C14 H14A 110.9 . . ?
C13 C14 H14B 110.9 . . ?
H14A C14 H14B 109.0 . . ?
C15 C14 C13 104.1(4) . . ?
C15 C14 H14A 110.9 . . ?
C15 C14 H14B 110.9 . . ?
N2 C15 C11 111.8(4) . . ?
N2 C15 C14 113.3(4) . . ?
N2 C15 H15 108.8 . . ?
C11 C15 C14 105.2(4) . . ?
C11 C15 H15 108.8 . . ?
C14 C15 H15 108.8 . . ?
C17 C16 N2 119.4(5) . . ?
C21 C16 N2 119.5(5) . . ?
C21 C16 C17 121.0(4) . . ?
C16 C17 H17 120.7 . . ?
C18 C17 C16 118.6(5) . . ?
C18 C17 H17 120.7 . . ?
C17 C18 H18 119.5 . . ?
C19 C18 C17 120.9(5) . . ?
C19 C18 H18 119.5 . . ?
C18 C19 H19 120.0 . . ?
C18 C19 C20 119.9(5) . . ?
C20 C19 H19 120.0 . . ?
C19 C20 H20 120.0 . . ?
C21 C20 C19 120.1(5) . . ?
C21 C20 H20 120.0 . . ?
C16 C21 C20 119.4(5) . . ?
C16 C21 H21 120.3 . . ?
C20 C21 H21 120.3 . . ?
N1 C22 Cu1 121.2(3) . . ?
N2 C22 Cu1 121.0(3) . . ?
N2 C22 N1 117.8(4) . . ?
C24 C23 H23 120.5 . . ?
C28 C23 H23 120.5 . . ?
C28 C23 C24 119.0(5) . . ?
C23 C24 H24 120.0 . . ?
C25 C24 C23 119.9(5) . . ?
C25 C24 H24 120.0 . . ?
C24 C25 H25 119.7 . . ?
C26 C25 C24 120.5(5) . . ?
C26 C25 H25 119.7 . . ?
C25 C26 H26 120.0 . . ?
C25 C26 C27 119.9(5) . . ?
C27 C26 H26 120.0 . . ?
C26 C27 H27 120.3 . . ?
C28 C27 C26 119.4(4) . . ?
C28 C27 H27 120.3 . . ?
C23 C28 N3 119.1(4) . . ?
C27 C28 N3 119.7(4) . . ?
C27 C28 C23 121.2(5) . . ?
N3 C29 H29 109.2 . . ?
N3 C29 C30 112.8(4) . . ?
N3 C29 C33 111.6(4) . . ?
C30 C29 H29 109.2 . . ?
C33 C29 H29 109.2 . . ?
C33 C29 C30 104.6(4) . . ?
C29 C30 H30A 111.0 . . ?
C29 C30 H30B 111.0 . . ?
H30A C30 H30B 109.0 . . ?
C31 C30 C29 104.0(4) . . ?
C31 C30 H30A 111.0 . . ?
C31 C30 H30B 111.0 . . ?
C30 C31 H31A 110.5 . . ?
C30 C31 H31B 110.5 . . ?
C30 C31 C32 106.3(4) . . ?
H31A C31 H31B 108.7 . . ?
C32 C31 H31A 110.5 . . ?
C32 C31 H31B 110.5 . . ?
C31 C32 H32A 110.7 . . ?
C31 C32 H32B 110.7 . . ?
H32A C32 H32B 108.8 . . ?
C33 C32 C31 105.1(4) . . ?
C33 C32 H32A 110.7 . . ?
C33 C32 H32B 110.7 . . ?
C29 C33 C32 101.1(4) . . ?
C29 C33 C34 114.5(4) . . ?
C29 C33 C37 112.6(3) . . ?
C32 C33 C34 115.1(4) . . ?
C32 C33 C37 110.2(4) . . ?
C37 C33 C34 103.6(4) . . ?
C33 C34 H34A 110.2 . . ?
C33 C34 H34B 110.2 . . ?
H34A C34 H34B 108.5 . . ?
C35 C34 C33 107.4(5) . . ?
C35 C34 H34A 110.2 . . ?
C35 C34 H34B 110.2 . . ?
C34 C35 H35A 110.8 . . ?
C34 C35 H35B 110.8 . . ?
H35A C35 H35B 108.9 . . ?
C36 C35 C34 104.5(4) . . ?
C36 C35 H35A 110.8 . . ?
C36 C35 H35B 110.8 . . ?
C35 C36 H36A 111.1 . . ?
C35 C36 H36B 111.1 . . ?
H36A C36 H36B 109.0 . . ?
C37 C36 C35 103.5(4) . . ?
C37 C36 H36A 111.1 . . ?
C37 C36 H36B 111.1 . . ?
N4 C37 C33 109.1(4) . . ?
N4 C37 C36 110.6(4) . . ?
N4 C37 H37 111.2 . . ?
C33 C37 H37 111.2 . . ?
C36 C37 C33 103.4(4) . . ?
C36 C37 H37 111.2 . . ?
N3 C38 Cu1 119.3(3) . . ?
N4 C38 Cu1 121.7(4) . . ?
N4 C38 N3 118.9(4) . . ?
C40 C39 N4 119.6(4) . . ?
C40 C39 C44 120.5(5) . . ?
C44 C39 N4 119.8(4) . . ?
C39 C40 H40 120.0 . . ?
C39 C40 C41 120.0(4) . . ?
C41 C40 H40 120.0 . . ?
C40 C41 H41 119.8 . . ?
C40 C41 C42 120.3(5) . . ?
C42 C41 H41 119.8 . . ?
C41 C42 H42 120.2 . . ?
C43 C42 C41 119.6(5) . . ?
C43 C42 H42 120.2 . . ?
C42 C43 H43 119.9 . . ?
C42 C43 C44 120.2(5) . . ?
C44 C43 H43 119.9 . . ?
C39 C44 C43 119.3(5) . . ?
C39 C44 H44 120.3 . . ?
C43 C44 H44 120.3 . . ?
O1 C45 H45A 110.1 . . ?
O1 C45 H45B 110.1 . . ?
O1 C45 H45C 110.8 . . ?
O1 C45 H45D 110.8 . . ?
O1 C45 C1A 107.8(10) . . ?
O1 C45 C1B 104.6(10) . . ?
H45A C45 H45B 108.5 . . ?
H45C C45 H45D 108.9 . . ?
C1A C45 H45A 110.1 . . ?
C1A C45 H45B 110.1 . . ?
C1B C45 H45C 110.8 . . ?
C1B C45 H45D 110.8 . . ?
H47A C47 H47B 108.8 . . ?
H47C C47 H47D 109.2 . . ?
C48 C47 H47A 110.6 . . ?
C48 C47 H47B 110.6 . . ?
C48 C47 H47C 111.3 . . ?
C48 C47 H47D 111.3 . . ?
C48 C47 C1A 105.5(8) . . ?
C1A C47 H47A 110.6 . . ?
C1A C47 H47B 110.6 . . ?
C1B C47 H47C 111.3 . . ?
C1B C47 H47D 111.3 . . ?
C1B C47 C48 102.3(10) . . ?
O1 C48 C47 106.5(6) . . ?
O1 C48 H48A 110.4 . . ?
O1 C48 H48B 110.4 . . ?
C47 C48 H48A 110.4 . . ?
C47 C48 H48B 110.4 . . ?
H48A C48 H48B 108.6 . . ?
C45 C1A C47 103.9(13) . . ?
C45 C1A H1AA 111.0 . . ?
C45 C1A H1AB 111.0 . . ?
C47 C1A H1AA 111.0 . . ?
C47 C1A H1AB 111.0 . . ?
H1AA C1A H1AB 109.0 . . ?
C45 C1B H1BA 110.9 . . ?
C45 C1B H1BB 110.9 . . ?
C47 C1B C45 104.1(12) . . ?
C47 C1B H1BA 110.9 . . ?
C47 C1B H1BB 110.9 . . ?
H1BA C1B H1BB 109.0 . . ?

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
O1 C45 C1A C47 -25.0(15) . . . . ?
O1 C45 C1B C47 26.6(15) . . . . ?
N1 C7 C8 C9 83.2(6) . . . . ?
N1 C7 C11 C10 -77.4(5) . . . . ?
N1 C7 C11 C12 160.4(4) . . . . ?
N1 C7 C11 C15 47.8(5) . . . . ?
N2 C16 C17 C18 174.7(4) . . . . ?
N2 C16 C21 C20 -173.6(5) . . . . ?
N3 C29 C30 C31 -154.4(4) . . . . ?
N3 C29 C33 C32 165.9(4) . . . . ?
N3 C29 C33 C34 -69.7(5) . . . . ?
N3 C29 C33 C37 48.3(5) . . . . ?
N4 C39 C40 C41 -175.0(4) . . . . ?
N4 C39 C44 C43 174.9(4) . . . . ?
C1 C2 C3 C4 -0.2(8) . . . . ?
C2 C1 C6 N1 -173.7(4) . . . . ?
C2 C1 C6 C5 2.7(7) . . . . ?
C2 C3 C4 C5 0.8(9) . . . . ?
C3 C4 C5 C6 0.3(8) . . . . ?
C4 C5 C6 N1 174.4(5) . . . . ?
C4 C5 C6 C1 -2.1(7) . . . . ?
C6 N1 C7 C8 44.8(6) . . . . ?
C6 N1 C7 C11 157.1(4) . . . . ?
C6 N1 C22 Cu1 -3.2(6) . . . . ?
C6 N1 C22 N2 177.8(4) . . . . ?
C6 C1 C2 C3 -1.6(8) . . . . ?
C7 N1 C6 C1 -124.2(5) . . . . ?
C7 N1 C6 C5 59.3(6) . . . . ?
C7 N1 C22 Cu1 -179.8(4) . . . . ?
C7 N1 C22 N2 1.3(8) . . . . ?
C7 C8 C9 C10 11.4(7) . . . . ?
C7 C11 C12 C13 -81.4(5) . . . . ?
C7 C11 C15 N2 -47.1(5) . . . . ?
C7 C11 C15 C14 76.3(5) . . . . ?
C8 C7 C11 C10 40.5(5) . . . . ?
C8 C7 C11 C12 -81.7(5) . . . . ?
C8 C7 C11 C15 165.7(4) . . . . ?
C8 C9 C10 C11 14.2(7) . . . . ?
C9 C10 C11 C7 -34.0(6) . . . . ?
C9 C10 C11 C12 86.4(6) . . . . ?
C9 C10 C11 C15 -156.2(5) . . . . ?
C10 C11 C12 C13 163.3(5) . . . . ?
C10 C11 C15 N2 70.0(5) . . . . ?
C10 C11 C15 C14 -166.6(4) . . . . ?
C11 C7 C8 C9 -32.4(5) . . . . ?
C11 C12 C13 C14 -19.3(6) . . . . ?
C12 C11 C15 N2 -165.8(4) . . . . ?
C12 C11 C15 C14 -42.4(5) . . . . ?
C12 C13 C14 C15 -6.6(5) . . . . ?
C13 C14 C15 N2 153.1(4) . . . . ?
C13 C14 C15 C11 30.6(5) . . . . ?
C15 N2 C16 C17 56.4(7) . . . . ?
C15 N2 C16 C21 -127.3(5) . . . . ?
C15 N2 C22 Cu1 -177.4(4) . . . . ?
C15 N2 C22 N1 1.5(7) . . . . ?
C15 C11 C12 C13 37.7(5) . . . . ?
C16 N2 C15 C11 -159.8(5) . . . . ?
C16 N2 C15 C14 81.5(6) . . . . ?
C16 N2 C22 Cu1 4.6(6) . . . . ?
C16 N2 C22 N1 -176.4(5) . . . . ?
C16 C17 C18 C19 -0.3(8) . . . . ?
C17 C16 C21 C20 2.7(7) . . . . ?
C17 C18 C19 C20 1.2(8) . . . . ?
C18 C19 C20 C21 0.0(8) . . . . ?
C19 C20 C21 C16 -1.9(8) . . . . ?
C21 C16 C17 C18 -1.7(7) . . . . ?
C22 N1 C6 C1 59.0(6) . . . . ?
C22 N1 C6 C5 -117.5(5) . . . . ?
C22 N1 C7 C8 -138.9(5) . . . . ?
C22 N1 C7 C11 -26.5(7) . . . . ?
C22 N2 C15 C11 22.3(7) . . . . ?
C22 N2 C15 C14 -96.4(6) . . . . ?
C22 N2 C16 C17 -125.5(5) . . . . ?
C22 N2 C16 C21 50.8(6) . . . . ?
C23 C24 C25 C26 0.3(8) . . . . ?
C24 C23 C28 N3 173.9(4) . . . . ?
C24 C23 C28 C27 -2.8(7) . . . . ?
C24 C25 C26 C27 -1.0(8) . . . . ?
C25 C26 C27 C28 -0.3(7) . . . . ?
C26 C27 C28 N3 -174.5(4) . . . . ?
C26 C27 C28 C23 2.2(7) . . . . ?
C28 N3 C29 C30 -86.7(5) . . . . ?
C28 N3 C29 C33 155.8(4) . . . . ?
C28 N3 C38 Cu1 -2.1(5) . . . . ?
C28 N3 C38 N4 178.3(4) . . . . ?
C28 C23 C24 C25 1.5(8) . . . . ?
C29 N3 C28 C23 113.2(5) . . . . ?
C29 N3 C28 C27 -70.1(6) . . . . ?
C29 N3 C38 Cu1 -175.3(3) . . . . ?
C29 N3 C38 N4 5.0(6) . . . . ?
C29 C30 C31 C32 8.8(6) . . . . ?
C29 C33 C34 C35 135.6(4) . . . . ?
C29 C33 C37 N4 -40.4(5) . . . . ?
C29 C33 C37 C36 -158.1(4) . . . . ?
C30 C29 C33 C32 43.6(5) . . . . ?
C30 C29 C33 C34 168.0(4) . . . . ?
C30 C29 C33 C37 -74.0(4) . . . . ?
C30 C31 C32 C33 17.8(6) . . . . ?
C31 C32 C33 C29 -37.6(5) . . . . ?
C31 C32 C33 C34 -161.6(5) . . . . ?
C31 C32 C33 C37 81.6(5) . . . . ?
C32 C33 C34 C35 -107.8(5) . . . . ?
C32 C33 C37 N4 -152.4(4) . . . . ?
C32 C33 C37 C36 89.9(4) . . . . ?
C33 C29 C30 C31 -32.9(5) . . . . ?
C33 C34 C35 C36 13.1(5) . . . . ?
C34 C33 C37 N4 83.9(4) . . . . ?
C34 C33 C37 C36 -33.8(4) . . . . ?
C34 C35 C36 C37 -34.4(5) . . . . ?
C35 C36 C37 N4 -74.0(5) . . . . ?
C35 C36 C37 C33 42.7(5) . . . . ?
C37 N4 C38 Cu1 -176.7(3) . . . . ?
C37 N4 C38 N3 2.9(7) . . . . ?
C37 N4 C39 C40 -62.7(5) . . . . ?
C37 N4 C39 C44 120.5(5) . . . . ?
C37 C33 C34 C35 12.6(5) . . . . ?
C38 N3 C28 C23 -60.2(6) . . . . ?
C38 N3 C28 C27 116.5(5) . . . . ?
C38 N3 C29 C30 86.3(5) . . . . ?
C38 N3 C29 C33 -31.2(6) . . . . ?
C38 N4 C37 C33 15.7(6) . . . . ?
C38 N4 C37 C36 128.8(5) . . . . ?
C38 N4 C39 C40 115.8(5) . . . . ?
C38 N4 C39 C44 -61.0(5) . . . . ?
C39 N4 C37 C33 -166.0(4) . . . . ?
C39 N4 C37 C36 -52.9(5) . . . . ?
C39 N4 C38 Cu1 4.9(5) . . . . ?
C39 N4 C38 N3 -175.4(4) . . . . ?
C39 C40 C41 C42 -0.2(8) . . . . ?
C40 C39 C44 C43 -1.9(7) . . . . ?
C40 C41 C42 C43 -1.5(8) . . . . ?
C41 C42 C43 C44 1.4(8) . . . . ?
C42 C43 C44 C39 0.2(8) . . . . ?
C44 C39 C40 C41 1.9(7) . . . . ?
C45 O1 C48 C47 -16.0(9) . . . . ?
C48 O1 C45 C1A 26.6(12) . . . . ?
C48 O1 C45 C1B -5.9(11) . . . . ?
C48 C47 C1A C45 14.9(16) . . . . ?
C48 C47 C1B C45 -35.1(14) . . . . ?
C1A C45 C1B C47 -74(3) . . . . ?
C1A C47 C48 O1 0.2(12) . . . . ?
C1A C47 C1B C45 64.5(19) . . . . ?
C1B C45 C1A C47 64(2) . . . . ?
C1B C47 C48 O1 32.7(12) . . . . ?
C1B C47 C1A C45 -73(2) . . . . ?

_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_shelxl_version_number           2013-2
_database_code_depnum_ccdc_archive 'CCDC 973600'
#######################################################################
#
#                 Cambridge Crystallographic Data Centre
#                                CCDC 
# 
#######################################################################
# 
#  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.
#
#  This CIF is provided on the understanding that it is used for bona
#  fide research purposes only. It may contain copyright material
#  of the CCDC or of third parties, and may not be copied or further
#  disseminated in any form, whether machine-readable or not,
#  except for the purpose of generating routine backup copies
#  on your local computer system.
# 
#  For further information on the CCDC, data deposition and
#  data retrieval see:
#                         www.ccdc.cam.ac.uk
#
#  Bona fide researchers may freely download Mercury and enCIFer
#  from this site to visualise CIF-encoded structures and 
#  to carry out CIF format checking respectively.
#
data_tuyq0320
_audit_creation_date             2013-10-30
_audit_creation_method           
;
Olex2 1.2
(compiled 2013.09.17 svn.r2790 for OlexSys, GUI svn.r4601)
;
_shelxl_version_number           2013-2
_chemical_name_common            ?
_chemical_name_systematic        
;
 ?
;
_chemical_formula_moiety         'C22 H24 N2'
_chemical_formula_sum            'C22 H24 N2'
_chemical_formula_weight         316.43
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 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'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      orthorhombic
_space_group_IT_number           61
_space_group_name_H-M_alt        'P b c a'
_space_group_name_Hall           '-P 2ac 2ab'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'x+1/2, -y+1/2, -z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, y, -z-1/2'
'-x-1/2, y-1/2, z'
'x, -y-1/2, z-1/2'

_cell_length_a                   12.4457(9)
_cell_length_b                   9.7837(5)
_cell_length_c                   28.322(2)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     3448.7(4)
_cell_formula_units_Z            8
_cell_measurement_reflns_used    1430
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      22.4160
_cell_measurement_theta_min      3.8730
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.071
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.97075
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.24 (release 03-12-2012 CrysAlis171 .NET)
(compiled Dec  3 2012,18:21:49)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            'clear light colourless'
_exptl_crystal_density_diffrn    1.219
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             1360
_exptl_crystal_size_max          0.3500
_exptl_crystal_size_mid          0.3200
_exptl_crystal_size_min          0.2200
_exptl_special_details           
;
 ?
;
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0860
_diffrn_reflns_av_unetI/netI     0.1314
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       27
_diffrn_reflns_limit_l_min       -35
_diffrn_reflns_number            9440
_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_theta_full        25.500
_diffrn_reflns_theta_max         26.363
_diffrn_reflns_theta_min         3.014
_diffrn_ambient_temperature      293(2)
_diffrn_detector_area_resol_mean 16.0733
_diffrn_measured_fraction_theta_full 0.9940
_diffrn_measured_fraction_theta_max 0.9021
_diffrn_measurement_details      
;
#__ type_ start__ end____ width___ exp.time_
  1 omega -103.00  -62.20   1.2000   24.0000
omega____ theta____ kappa____ phi______ frames
    -      -19.2137  178.0000  -90.0000 34

#__ type_ start__ end____ width___ exp.time_
  2 omega  -52.00   60.80   1.2000   24.0000
omega____ theta____ kappa____ phi______ frames
    -       22.6512  -19.0000   30.0000 94

#__ type_ start__ end____ width___ exp.time_
  3 omega   29.00   56.60   1.2000   24.0000
omega____ theta____ kappa____ phi______ frames
    -       22.6512  -38.0000  120.0000 23
;
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, Eos'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_UB_11      -0.0392179000
_diffrn_orient_matrix_UB_12      -0.0178040000
_diffrn_orient_matrix_UB_13      0.0170754000
_diffrn_orient_matrix_UB_21      -0.0370983000
_diffrn_orient_matrix_UB_22      -0.0147447000
_diffrn_orient_matrix_UB_23      -0.0183120000
_diffrn_orient_matrix_UB_31      0.0181895000
_diffrn_orient_matrix_UB_32      -0.0687505000
_diffrn_orient_matrix_UB_33      -0.0005000000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.7107
_diffrn_source                   'SuperNova (Mo) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                1789
_reflns_number_total             3515
_reflns_odcompleteness_completeness 99.40
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     26.32
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.24 (release 03-12-2012 CrysAlis171 .NET)
(compiled Dec  3 2012,18:21:49)
;
_computing_data_collection       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.24 (release 03-12-2012 CrysAlis171 .NET)
(compiled Dec  3 2012,18:21:49)
;
_computing_data_reduction        
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.24 (release 03-12-2012 CrysAlis171 .NET)
(compiled Dec  3 2012,18:21:49)
;
_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  
;
SHELX, G.M. Sheldrick, Acta Cryst.
(2008). A64, 112-122
;
_computing_structure_solution    'SUPERFLIP, J. Appl. Cryst. (2007) 40, 786-790'
_refine_diff_density_max         0.292
_refine_diff_density_min         -0.238
_refine_diff_density_rms         0.061
_refine_ls_extinction_coef       0.0048(9)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_ref   1.025
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     225
_refine_ls_number_reflns         3515
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1496
_refine_ls_R_factor_gt           0.0734
_refine_ls_restrained_S_all      1.025
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
;
 w=1/[σ²(Fo²)+(0.0689P)²]
 where P=(Fo²+2Fc²)/3
;
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1593
_refine_ls_wR_factor_ref         0.2098
_refine_special_details          
;
 ?
;
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
2.a Ternary CH refined with riding coordinates:
 C2(H2), C4(H4)
2.b Secondary CH2 refined with riding coordinates:
 C11(H11A,H11B), C12(H12A,H12B), C14(H14A,H14B), C15(H15A,H15B), C16(H16A,H16B)
2.c Aromatic/amide H refined with riding coordinates:
 C6(H6), C7(H7), C8(H8), C9(H9), C10(H10), C18(H18), C19(H19), C20(H20),
 C21(H21), C22(H22)
;
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     iterative
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
N1 N 0.3228(2) 0.9028(2) 0.65634(9) 0.0258(7) Uani 1 1 d . . . . .
N2 N 0.4613(2) 0.8269(2) 0.60976(9) 0.0271(7) Uani 1 1 d . . . . .
C1 C 0.3901(2) 0.7992(3) 0.64472(11) 0.0255(8) Uani 1 1 d . . . . .
C2 C 0.3164(3) 1.0341(3) 0.63106(11) 0.0279(8) Uani 1 1 d . . . . .
H2 H 0.2896 1.1045 0.6527 0.034 Uiso 1 1 calc R U . . .
C3 C 0.4276(3) 1.0761(3) 0.61319(11) 0.0275(8) Uani 1 1 d . . . . .
C4 C 0.4792(3) 0.9598(3) 0.58517(12) 0.0289(8) Uani 1 1 d . . . . .
H4 H 0.4512 0.9569 0.5528 0.035 Uiso 1 1 calc R U . . .
C5 C 0.2467(3) 0.8782(3) 0.69342(10) 0.0256(8) Uani 1 1 d . . . . .
C6 C 0.1504(3) 0.9489(3) 0.69497(11) 0.0308(8) Uani 1 1 d . . . . .
H6 H 0.1355 1.0150 0.6723 0.037 Uiso 1 1 calc R U . . .
C7 C 0.0765(3) 0.9214(3) 0.73008(12) 0.0366(9) Uani 1 1 d . . . . .
H7 H 0.0122 0.9698 0.7308 0.044 Uiso 1 1 calc R U . . .
C8 C 0.0963(3) 0.8238(3) 0.76403(13) 0.0392(9) Uani 1 1 d . . . . .
H8 H 0.0452 0.8043 0.7870 0.047 Uiso 1 1 calc R U . . .
C9 C 0.1936(3) 0.7552(4) 0.76322(12) 0.0380(9) Uani 1 1 d . . . . .
H9 H 0.2085 0.6900 0.7862 0.046 Uiso 1 1 calc R U . . .
C10 C 0.2691(3) 0.7824(3) 0.72855(12) 0.0324(9) Uani 1 1 d . . . . .
H10 H 0.3347 0.7369 0.7287 0.039 Uiso 1 1 calc R U . . .
C11 C 0.2465(3) 1.0332(3) 0.58646(11) 0.0304(8) Uani 1 1 d . . . . .
H11A H 0.1722 1.0528 0.5942 0.036 Uiso 1 1 calc R U . . .
H11B H 0.2501 0.9449 0.5710 0.036 Uiso 1 1 calc R U . . .
C12 C 0.2933(3) 1.1455(3) 0.55443(12) 0.0352(9) Uani 1 1 d . . . . .
H12A H 0.2430 1.2207 0.5511 0.042 Uiso 1 1 calc R U . . .
H12B H 0.3096 1.1095 0.5233 0.042 Uiso 1 1 calc R U . . .
C13 C 0.3968(3) 1.1931(3) 0.57968(12) 0.0299(8) Uani 1 1 d . . . . .
H13A H 0.380(3) 1.275(3) 0.5992(12) 0.036 Uiso 1 1 d . U . . .
H13B H 0.455(2) 1.221(3) 0.5559(11) 0.021(8) Uiso 1 1 d . . . . .
C14 C 0.5094(3) 1.1137(3) 0.65140(13) 0.0344(9) Uani 1 1 d . . . . .
H14A H 0.5068 1.2109 0.6580 0.041 Uiso 1 1 calc R U . . .
H14B H 0.4947 1.0641 0.6803 0.041 Uiso 1 1 calc R U . . .
C15 C 0.6176(3) 1.0746(4) 0.63195(14) 0.0498(11) Uani 1 1 d . . . . .
H15A H 0.6551 1.0160 0.6541 0.060 Uiso 1 1 calc R U . . .
H15B H 0.6608 1.1557 0.6266 0.060 Uiso 1 1 calc R U . . .
C16 C 0.5994(3) 0.9991(3) 0.58547(13) 0.0371(9) Uani 1 1 d . . . . .
H16A H 0.6441 0.9181 0.5838 0.045 Uiso 1 1 calc R U . . .
H16B H 0.6162 1.0578 0.5589 0.045 Uiso 1 1 calc R U . . .
C17 C 0.5213(3) 0.7103(3) 0.59356(12) 0.0274(8) Uani 1 1 d . . . . .
C18 C 0.5447(3) 0.6948(3) 0.54590(12) 0.0345(9) Uani 1 1 d . . . . .
H18 H 0.5244 0.7620 0.5245 0.041 Uiso 1 1 calc R U . . .
C19 C 0.5981(3) 0.5793(3) 0.53031(13) 0.0393(10) Uani 1 1 d . . . . .
H19 H 0.6141 0.5703 0.4984 0.047 Uiso 1 1 calc R U . . .
C20 C 0.6278(3) 0.4781(3) 0.56104(13) 0.0379(9) Uani 1 1 d . . . . .
H20 H 0.6616 0.3995 0.5500 0.045 Uiso 1 1 calc R U . . .
C21 C 0.6069(3) 0.4945(3) 0.60879(13) 0.0329(9) Uani 1 1 d . . . . .
H21 H 0.6279 0.4271 0.6300 0.040 Uiso 1 1 calc R U . . .
C22 C 0.5548(3) 0.6104(3) 0.62515(12) 0.0297(8) Uani 1 1 d . . . . .
H22 H 0.5423 0.6213 0.6573 0.036 Uiso 1 1 calc R U . . .


_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
N1 C1 1.356(4) . ?
N1 C2 1.473(4) . ?
N1 C5 1.435(4) . ?
N2 C1 1.357(4) . ?
N2 C4 1.492(4) . ?
N2 C17 1.438(4) . ?
C2 H2 0.9800 . ?
C2 C3 1.530(4) . ?
C2 C11 1.533(4) . ?
C3 C4 1.529(4) . ?
C3 C13 1.535(4) . ?
C3 C14 1.531(5) . ?
C4 H4 0.9800 . ?
C4 C16 1.544(5) . ?
C5 C6 1.384(4) . ?
C5 C10 1.395(4) . ?
C6 H6 0.9300 . ?
C6 C7 1.381(5) . ?
C7 H7 0.9300 . ?
C7 C8 1.378(5) . ?
C8 H8 0.9300 . ?
C8 C9 1.386(5) . ?
C9 H9 0.9300 . ?
C9 C10 1.385(5) . ?
C10 H10 0.9300 . ?
C11 H11A 0.9700 . ?
C11 H11B 0.9700 . ?
C11 C12 1.539(4) . ?
C12 H12A 0.9700 . ?
C12 H12B 0.9700 . ?
C12 C13 1.546(5) . ?
C13 H13A 0.99(3) . ?
C13 H13B 1.02(3) . ?
C14 H14A 0.9700 . ?
C14 H14B 0.9700 . ?
C14 C15 1.504(5) . ?
C15 H15A 0.9700 . ?
C15 H15B 0.9700 . ?
C15 C16 1.526(5) . ?
C16 H16A 0.9700 . ?
C16 H16B 0.9700 . ?
C17 C18 1.389(4) . ?
C17 C22 1.390(4) . ?
C18 H18 0.9300 . ?
C18 C19 1.383(4) . ?
C19 H19 0.9300 . ?
C19 C20 1.369(5) . ?
C20 H20 0.9300 . ?
C20 C21 1.387(5) . ?
C21 H21 0.9300 . ?
C21 C22 1.385(4) . ?
C22 H22 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
C1 N1 C2 124.6(3) . . ?
C1 N1 C5 117.4(2) . . ?
C5 N1 C2 117.8(2) . . ?
C1 N2 C4 127.8(2) . . ?
C1 N2 C17 114.4(2) . . ?
C17 N2 C4 117.7(2) . . ?
N1 C1 N2 115.6(3) . . ?
N1 C2 H2 109.1 . . ?
N1 C2 C3 110.2(3) . . ?
N1 C2 C11 115.2(3) . . ?
C3 C2 H2 109.1 . . ?
C3 C2 C11 104.0(3) . . ?
C11 C2 H2 109.1 . . ?
C2 C3 C13 100.3(3) . . ?
C2 C3 C14 115.6(3) . . ?
C4 C3 C2 110.7(2) . . ?
C4 C3 C13 109.8(3) . . ?
C4 C3 C14 105.5(3) . . ?
C14 C3 C13 115.0(3) . . ?
N2 C4 C3 110.1(2) . . ?
N2 C4 H4 110.9 . . ?
N2 C4 C16 111.1(3) . . ?
C3 C4 H4 110.9 . . ?
C3 C4 C16 102.6(2) . . ?
C16 C4 H4 110.9 . . ?
C6 C5 N1 120.7(3) . . ?
C6 C5 C10 119.1(3) . . ?
C10 C5 N1 120.2(3) . . ?
C5 C6 H6 119.9 . . ?
C7 C6 C5 120.2(3) . . ?
C7 C6 H6 119.9 . . ?
C6 C7 H7 119.4 . . ?
C8 C7 C6 121.2(3) . . ?
C8 C7 H7 119.4 . . ?
C7 C8 H8 120.6 . . ?
C7 C8 C9 118.7(3) . . ?
C9 C8 H8 120.6 . . ?
C8 C9 H9 119.6 . . ?
C10 C9 C8 120.8(3) . . ?
C10 C9 H9 119.6 . . ?
C5 C10 H10 120.0 . . ?
C9 C10 C5 120.0(3) . . ?
C9 C10 H10 120.0 . . ?
C2 C11 H11A 110.6 . . ?
C2 C11 H11B 110.6 . . ?
C2 C11 C12 105.5(3) . . ?
H11A C11 H11B 108.8 . . ?
C12 C11 H11A 110.6 . . ?
C12 C11 H11B 110.6 . . ?
C11 C12 H12A 110.8 . . ?
C11 C12 H12B 110.8 . . ?
C11 C12 C13 104.9(3) . . ?
H12A C12 H12B 108.8 . . ?
C13 C12 H12A 110.8 . . ?
C13 C12 H12B 110.8 . . ?
C3 C13 C12 105.7(3) . . ?
C3 C13 H13A 108.0(19) . . ?
C3 C13 H13B 115.3(16) . . ?
C12 C13 H13A 108.8(19) . . ?
C12 C13 H13B 111.3(16) . . ?
H13A C13 H13B 108(2) . . ?
C3 C14 H14A 110.5 . . ?
C3 C14 H14B 110.5 . . ?
H14A C14 H14B 108.7 . . ?
C15 C14 C3 106.0(3) . . ?
C15 C14 H14A 110.5 . . ?
C15 C14 H14B 110.5 . . ?
C14 C15 H15A 110.1 . . ?
C14 C15 H15B 110.1 . . ?
C14 C15 C16 107.8(3) . . ?
H15A C15 H15B 108.5 . . ?
C16 C15 H15A 110.1 . . ?
C16 C15 H15B 110.1 . . ?
C4 C16 H16A 110.6 . . ?
C4 C16 H16B 110.6 . . ?
C15 C16 C4 105.6(3) . . ?
C15 C16 H16A 110.6 . . ?
C15 C16 H16B 110.6 . . ?
H16A C16 H16B 108.7 . . ?
C18 C17 N2 120.4(3) . . ?
C18 C17 C22 119.1(3) . . ?
C22 C17 N2 120.6(3) . . ?
C17 C18 H18 120.0 . . ?
C19 C18 C17 120.0(3) . . ?
C19 C18 H18 120.0 . . ?
C18 C19 H19 119.4 . . ?
C20 C19 C18 121.2(3) . . ?
C20 C19 H19 119.4 . . ?
C19 C20 H20 120.5 . . ?
C19 C20 C21 119.0(3) . . ?
C21 C20 H20 120.5 . . ?
C20 C21 H21 119.7 . . ?
C22 C21 C20 120.6(3) . . ?
C22 C21 H21 119.7 . . ?
C17 C22 H22 120.0 . . ?
C21 C22 C17 120.0(3) . . ?
C21 C22 H22 120.0 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
N1 C2 C3 C4 51.9(3) . . . . ?
N1 C2 C3 C13 167.8(2) . . . . ?
N1 C2 C3 C14 -67.8(3) . . . . ?
N1 C2 C11 C12 -152.7(3) . . . . ?
N1 C5 C6 C7 178.2(3) . . . . ?
N1 C5 C10 C9 -177.5(3) . . . . ?
N2 C4 C16 C15 -86.4(3) . . . . ?
N2 C17 C18 C19 -177.0(3) . . . . ?
N2 C17 C22 C21 176.1(3) . . . . ?
C1 N1 C2 C3 -34.7(4) . . . . ?
C1 N1 C2 C11 82.5(4) . . . . ?
C1 N1 C5 C6 -153.2(3) . . . . ?
C1 N1 C5 C10 27.0(4) . . . . ?
C1 N2 C4 C3 15.5(4) . . . . ?
C1 N2 C4 C16 128.4(3) . . . . ?
C1 N2 C17 C18 141.6(3) . . . . ?
C1 N2 C17 C22 -37.2(4) . . . . ?
C2 N1 C1 N2 5.8(4) . . . . ?
C2 N1 C5 C6 21.9(4) . . . . ?
C2 N1 C5 C10 -158.0(3) . . . . ?
C2 C3 C4 N2 -42.8(4) . . . . ?
C2 C3 C4 C16 -161.1(3) . . . . ?
C2 C3 C13 C12 -39.6(3) . . . . ?
C2 C3 C14 C15 149.1(3) . . . . ?
C2 C11 C12 C13 7.0(3) . . . . ?
C3 C2 C11 C12 -32.0(3) . . . . ?
C3 C4 C16 C15 31.2(3) . . . . ?
C3 C14 C15 C16 -6.6(4) . . . . ?
C4 N2 C1 N1 4.6(4) . . . . ?
C4 N2 C17 C18 -35.2(4) . . . . ?
C4 N2 C17 C22 146.1(3) . . . . ?
C4 C3 C13 C12 76.9(3) . . . . ?
C4 C3 C14 C15 26.5(3) . . . . ?
C5 N1 C1 N2 -179.5(3) . . . . ?
C5 N1 C2 C3 150.7(3) . . . . ?
C5 N1 C2 C11 -92.1(3) . . . . ?
C5 C6 C7 C8 -0.2(5) . . . . ?
C6 C5 C10 C9 2.6(5) . . . . ?
C6 C7 C8 C9 1.7(5) . . . . ?
C7 C8 C9 C10 -1.0(5) . . . . ?
C8 C9 C10 C5 -1.2(5) . . . . ?
C10 C5 C6 C7 -2.0(5) . . . . ?
C11 C2 C3 C4 -72.1(3) . . . . ?
C11 C2 C3 C13 43.8(3) . . . . ?
C11 C2 C3 C14 168.1(3) . . . . ?
C11 C12 C13 C3 20.5(3) . . . . ?
C13 C3 C4 N2 -152.6(3) . . . . ?
C13 C3 C4 C16 89.1(3) . . . . ?
C13 C3 C14 C15 -94.6(3) . . . . ?
C14 C3 C4 N2 82.9(3) . . . . ?
C14 C3 C4 C16 -35.4(3) . . . . ?
C14 C3 C13 C12 -164.3(3) . . . . ?
C14 C15 C16 C4 -15.5(4) . . . . ?
C17 N2 C1 N1 -171.7(3) . . . . ?
C17 N2 C4 C3 -168.3(3) . . . . ?
C17 N2 C4 C16 -55.3(3) . . . . ?
C17 C18 C19 C20 0.7(5) . . . . ?
C18 C17 C22 C21 -2.6(5) . . . . ?
C18 C19 C20 C21 -2.1(5) . . . . ?
C19 C20 C21 C22 1.2(5) . . . . ?
C20 C21 C22 C17 1.2(5) . . . . ?
C22 C17 C18 C19 1.7(5) . . . . ?

_database_code_depnum_ccdc_archive 'CCDC 973601'
#######################################################################
#
#                 Cambridge Crystallographic Data Centre
#                                CCDC 
# 
#######################################################################
# 
#  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.
#
#  This CIF is provided on the understanding that it is used for bona
#  fide research purposes only. It may contain copyright material
#  of the CCDC or of third parties, and may not be copied or further
#  disseminated in any form, whether machine-readable or not,
#  except for the purpose of generating routine backup copies
#  on your local computer system.
# 
#  For further information on the CCDC, data deposition and
#  data retrieval see:
#                         www.ccdc.cam.ac.uk
#
#  Bona fide researchers may freely download Mercury and enCIFer
#  from this site to visualise CIF-encoded structures and 
#  to carry out CIF format checking respectively.
#
data_yangbm0304
_audit_creation_date             2013-10-30
_audit_creation_method           
;
Olex2 1.2
(compiled 2013.09.17 svn.r2790 for OlexSys, GUI svn.r4601)
;
_shelxl_version_number           2013-2
_chemical_name_common            ?
_chemical_name_systematic        
;
 ?
;
_chemical_formula_moiety         'C30 H36 Cl N2 Rh'
_chemical_formula_sum            'C30 H36 Cl N2 Rh'
_chemical_formula_weight         562.97
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 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'
Rh Rh -1.1178 0.9187 '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'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 1 21/n 1'
_space_group_name_Hall           '-P 2yn'
loop_
_space_group_symop_operation_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                   11.1034(3)
_cell_length_b                   19.4323(4)
_cell_length_c                   13.1451(3)
_cell_angle_alpha                90
_cell_angle_beta                 112.161(3)
_cell_angle_gamma                90
_cell_volume                     2626.73(12)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    5300
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      28.0870
_cell_measurement_theta_min      3.5560
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.773
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.89831
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.24 (release 03-12-2012 CrysAlis171 .NET)
(compiled Dec  3 2012,18:21:49)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_density_diffrn    1.424
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_F_000             1168
_exptl_crystal_size_max          ?
_exptl_crystal_size_mid          ?
_exptl_crystal_size_min          ?
_exptl_special_details           
;
 ?
;
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0288
_diffrn_reflns_av_unetI/netI     0.0445
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       24
_diffrn_reflns_limit_k_min       -21
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            12015
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_theta_full        25.500
_diffrn_reflns_theta_max         26.370
_diffrn_reflns_theta_min         3.037
_diffrn_ambient_temperature      293(2)
_diffrn_detector_area_resol_mean 16.0733
_diffrn_measured_fraction_theta_full 0.9977
_diffrn_measured_fraction_theta_max 0.8890
_diffrn_measurement_details      
;
#__ type_ start__ end____ width___ exp.time_
  1 omega  -20.00    6.00   1.0000   20.0000
omega____ theta____ kappa____ phi______ frames
    -      -19.2137  -99.0000   60.0000 26

#__ type_ start__ end____ width___ exp.time_
  2 omega   -3.00   89.00   1.0000   20.0000
omega____ theta____ kappa____ phi______ frames
    -       22.6512   57.0000  120.0000 92

#__ type_ start__ end____ width___ exp.time_
  3 omega   63.00   93.00   1.0000   20.0000
omega____ theta____ kappa____ phi______ frames
    -       22.6512   57.0000  150.0000 30

#__ type_ start__ end____ width___ exp.time_
  4 omega   -2.00   93.00   1.0000   20.0000
omega____ theta____ kappa____ phi______ frames
    -       22.6512   77.0000  -30.0000 95

#__ type_ start__ end____ width___ exp.time_
  5 omega   42.00   69.00   1.0000   20.0000
omega____ theta____ kappa____ phi______ frames
    -       22.6512  -99.0000  120.0000 27
;
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, Eos'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_UB_11      0.0670486000
_diffrn_orient_matrix_UB_12      -0.0063864000
_diffrn_orient_matrix_UB_13      0.0131294000
_diffrn_orient_matrix_UB_21      -0.0114928000
_diffrn_orient_matrix_UB_22      -0.0358947000
_diffrn_orient_matrix_UB_23      0.0004052000
_diffrn_orient_matrix_UB_31      -0.0113394000
_diffrn_orient_matrix_UB_32      -0.0017380000
_diffrn_orient_matrix_UB_33      -0.0567962000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.7107
_diffrn_source                   'SuperNova (Mo) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                4367
_reflns_number_total             5352
_reflns_odcompleteness_completeness 99.77
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     26.32
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.24 (release 03-12-2012 CrysAlis171 .NET)
(compiled Dec  3 2012,18:21:49)
;
_computing_data_collection       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.24 (release 03-12-2012 CrysAlis171 .NET)
(compiled Dec  3 2012,18:21:49)
;
_computing_data_reduction        
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.24 (release 03-12-2012 CrysAlis171 .NET)
(compiled Dec  3 2012,18:21:49)
;
_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  
;
SHELX, G.M. Sheldrick, Acta Cryst.
(2008). A64, 112-122
;
_computing_structure_solution    'SUPERFLIP, J. Appl. Cryst. (2007) 40, 786-790'
_refine_diff_density_max         0.405
_refine_diff_density_min         -0.491
_refine_diff_density_rms         0.063
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.032
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     307
_refine_ls_number_reflns         5352
_refine_ls_number_restraints     24
_refine_ls_R_factor_all          0.0485
_refine_ls_R_factor_gt           0.0356
_refine_ls_restrained_S_all      1.038
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
;
 w=1/[σ²(Fo²)+(0.0265P)²+0.9406P]
 where P=(Fo²+2Fc²)/3
;
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0710
_refine_ls_wR_factor_ref         0.0771
_refine_special_details          
;
 ?
;
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
2. Uiso/Uaniso restraints and constraints
Uanis(C14) \\sim Ueq, Uanis(C15) \\sim Ueq, Uanis(C16) \\sim Ueq, Uanis(C4)
\\sim Ueq: with sigma of 0.01 and sigma for terminal atoms of 0.02
3.a Ternary CH refined with riding coordinates:
 C2(H2), C4(H4), C23(H23), C26(H26), C27(H27), C30(H30)
3.b Secondary CH2 refined with riding coordinates:
 C11(H11A,H11B), C12(H12A,H12B), C13(H13A,H13B), C14(H14A,H14B), C15(H15A,
 H15B), C16(H16A,H16B), C24(H24A,H24B), C25(H25A,H25B), C28(H28A,H28B),
 C29(H29A,H29B)
3.c Aromatic/amide H refined with riding coordinates:
 C6(H6), C7(H7), C8(H8), C9(H9), C10(H10), C18(H18), C19(H19), C20(H20),
 C21(H21), C22(H22)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     iterative
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Rh1 Rh 0.11808(2) 0.64513(2) 0.29790(2) 0.03004(8) Uani 1 1 d . . . . .
Cl1 Cl 0.25704(8) 0.65311(4) 0.48998(6) 0.0510(2) Uani 1 1 d . . . . .
N1 N -0.0940(2) 0.72373(11) 0.33832(17) 0.0288(5) Uani 1 1 d . . . . .
N2 N 0.0477(2) 0.79117(11) 0.29162(18) 0.0319(5) Uani 1 1 d . . . . .
C1 C 0.0112(2) 0.72809(14) 0.3114(2) 0.0290(6) Uani 1 1 d . . . . .
C2 C -0.1707(3) 0.78359(13) 0.3477(2) 0.0337(6) Uani 1 1 d . . . . .
H2 H -0.2009 0.7746 0.4075 0.040 Uiso 1 1 calc R U . . .
C3 C -0.0910(3) 0.84891(14) 0.3746(2) 0.0348(7) Uani 1 1 d . . . . .
C4 C -0.0163(3) 0.85778(13) 0.2988(3) 0.0371(7) Uani 1 1 d . U . . .
H4 H -0.0737 0.8738 0.2259 0.045 Uiso 1 1 calc R U . . .
C5 C -0.1405(3) 0.65851(14) 0.3606(2) 0.0340(7) Uani 1 1 d . . . . .
C6 C -0.2639(3) 0.63603(16) 0.2942(3) 0.0492(8) Uani 1 1 d . . . . .
H6 H -0.3132 0.6616 0.2327 0.059 Uiso 1 1 calc R U . . .
C7 C -0.3139(4) 0.57601(18) 0.3188(3) 0.0617(10) Uani 1 1 d . . . . .
H7 H -0.3968 0.5616 0.2738 0.074 Uiso 1 1 calc R U . . .
C8 C -0.2431(4) 0.53778(18) 0.4083(3) 0.0639(11) Uani 1 1 d . . . . .
H8 H -0.2771 0.4974 0.4246 0.077 Uiso 1 1 calc R U . . .
C9 C -0.1203(4) 0.55974(17) 0.4742(3) 0.0572(10) Uani 1 1 d . . . . .
H9 H -0.0715 0.5339 0.5354 0.069 Uiso 1 1 calc R U . . .
C10 C -0.0685(3) 0.61994(16) 0.4505(2) 0.0421(7) Uani 1 1 d . . . . .
H10 H 0.0146 0.6340 0.4954 0.051 Uiso 1 1 calc R U . . .
C11 C -0.2892(3) 0.80111(15) 0.2446(3) 0.0463(8) Uani 1 1 d . . . . .
H11A H -0.3638 0.7739 0.2412 0.056 Uiso 1 1 calc R U . . .
H11B H -0.2713 0.7924 0.1789 0.056 Uiso 1 1 calc R U . . .
C12 C -0.3142(3) 0.87779(17) 0.2551(3) 0.0588(10) Uani 1 1 d . . . . .
H12A H -0.3236 0.9019 0.1879 0.071 Uiso 1 1 calc R U . . .
H12B H -0.3929 0.8842 0.2695 0.071 Uiso 1 1 calc R U . . .
C13 C -0.1968(3) 0.90459(15) 0.3505(2) 0.0434(7) Uani 1 1 d . . . . .
H13A H -0.2187 0.9122 0.4144 0.052 Uiso 1 1 calc R U . . .
H13B H -0.1668 0.9477 0.3310 0.052 Uiso 1 1 calc R U . . .
C14 C 0.0156(4) 0.85307(18) 0.4892(3) 0.0589(10) Uani 1 1 d . U . . .
H14A H -0.0182 0.8725 0.5411 0.071 Uiso 1 1 calc R U . . .
H14B H 0.0506 0.8077 0.5146 0.071 Uiso 1 1 calc R U . . .
C15 C 0.1192(5) 0.8993(3) 0.4771(4) 0.1077(17) Uani 1 1 d . U . . .
H15A H 0.1227 0.9425 0.5150 0.129 Uiso 1 1 calc R U . . .
H15B H 0.2037 0.8773 0.5088 0.129 Uiso 1 1 calc R U . . .
C16 C 0.0854(3) 0.91197(18) 0.3577(3) 0.0647(10) Uani 1 1 d . U . . .
H16A H 0.1615 0.9071 0.3390 0.078 Uiso 1 1 calc R U . . .
H16B H 0.0502 0.9579 0.3378 0.078 Uiso 1 1 calc R U . . .
C17 C 0.1498(3) 0.79630(14) 0.2490(2) 0.0360(7) Uani 1 1 d . . . . .
C18 C 0.1198(3) 0.81797(16) 0.1425(2) 0.0461(8) Uani 1 1 d . . . . .
H18 H 0.0347 0.8296 0.0987 0.055 Uiso 1 1 calc R U . . .
C19 C 0.2170(4) 0.82240(19) 0.1010(3) 0.0583(9) Uani 1 1 d . . . . .
H19 H 0.1966 0.8367 0.0289 0.070 Uiso 1 1 calc R U . . .
C20 C 0.3431(3) 0.80596(18) 0.1650(3) 0.0580(9) Uani 1 1 d . . . . .
H20 H 0.4079 0.8083 0.1364 0.070 Uiso 1 1 calc R U . . .
C21 C 0.3725(3) 0.78596(18) 0.2720(3) 0.0554(9) Uani 1 1 d . . . . .
H21 H 0.4580 0.7751 0.3159 0.066 Uiso 1 1 calc R U . . .
C22 C 0.2773(3) 0.78172(15) 0.3154(3) 0.0451(8) Uani 1 1 d . . . . .
H22 H 0.2986 0.7692 0.3884 0.054 Uiso 1 1 calc R U . . .
C23 C -0.0394(3) 0.60624(16) 0.1657(2) 0.0438(7) Uani 1 1 d . . . . .
H23 H -0.1227 0.6266 0.1590 0.053 Uiso 1 1 calc R U . . .
C24 C -0.0402(4) 0.52904(17) 0.1673(3) 0.0615(10) Uani 1 1 d . . . . .
H24A H -0.0927 0.5125 0.0943 0.074 Uiso 1 1 calc R U . . .
H24B H -0.0810 0.5137 0.2169 0.074 Uiso 1 1 calc R U . . .
C25 C 0.0931(4) 0.49745(17) 0.2025(3) 0.0683(11) Uani 1 1 d . . . . .
H25A H 0.1168 0.4927 0.1389 0.082 Uiso 1 1 calc R U . . .
H25B H 0.0913 0.4518 0.2317 0.082 Uiso 1 1 calc R U . . .
C26 C 0.1951(3) 0.54044(16) 0.2888(3) 0.0510(9) Uani 1 1 d . . . . .
H26 H 0.2375 0.5176 0.3598 0.061 Uiso 1 1 calc R U . . .
C27 C 0.2702(3) 0.58911(16) 0.2642(3) 0.0483(8) Uani 1 1 d . . . . .
H27 H 0.3575 0.5946 0.3209 0.058 Uiso 1 1 calc R U . . .
C28 C 0.2610(4) 0.6071(2) 0.1504(3) 0.0648(10) Uani 1 1 d . . . . .
H28A H 0.2946 0.5689 0.1215 0.078 Uiso 1 1 calc R U . . .
H28B H 0.3162 0.6466 0.1548 0.078 Uiso 1 1 calc R U . . .
C29 C 0.1243(4) 0.6234(2) 0.0701(3) 0.0625(10) Uani 1 1 d . . . . .
H29A H 0.1295 0.6583 0.0191 0.075 Uiso 1 1 calc R U . . .
H29B H 0.0872 0.5823 0.0280 0.075 Uiso 1 1 calc R U . . .
C30 C 0.0341(3) 0.64865(15) 0.1243(2) 0.0430(7) Uani 1 1 d . . . . .
H30 H -0.0081 0.6926 0.0951 0.052 Uiso 1 1 calc R U . . .


_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 2.4167(8) . ?
Rh1 C1 2.048(3) . ?
Rh1 C23 2.087(3) . ?
Rh1 C26 2.227(3) . ?
Rh1 C27 2.191(3) . ?
Rh1 C30 2.116(3) . ?
N1 C1 1.346(3) . ?
N1 C2 1.474(3) . ?
N1 C5 1.439(3) . ?
N2 C1 1.346(3) . ?
N2 C4 1.497(3) . ?
N2 C17 1.445(3) . ?
C2 H2 0.9800 . ?
C2 C3 1.510(4) . ?
C2 C11 1.529(4) . ?
C3 C4 1.527(4) . ?
C3 C13 1.539(4) . ?
C3 C14 1.527(4) . ?
C4 H4 0.9800 . ?
C4 C16 1.524(4) . ?
C5 C6 1.389(4) . ?
C5 C10 1.372(4) . ?
C6 H6 0.9300 . ?
C6 C7 1.381(4) . ?
C7 H7 0.9300 . ?
C7 C8 1.363(5) . ?
C8 H8 0.9300 . ?
C8 C9 1.378(5) . ?
C9 H9 0.9300 . ?
C9 C10 1.390(4) . ?
C10 H10 0.9300 . ?
C11 H11A 0.9700 . ?
C11 H11B 0.9700 . ?
C11 C12 1.531(4) . ?
C12 H12A 0.9700 . ?
C12 H12B 0.9700 . ?
C12 C13 1.520(4) . ?
C13 H13A 0.9700 . ?
C13 H13B 0.9700 . ?
C14 H14A 0.9700 . ?
C14 H14B 0.9700 . ?
C14 C15 1.515(6) . ?
C15 H15A 0.9700 . ?
C15 H15B 0.9700 . ?
C15 C16 1.489(6) . ?
C16 H16A 0.9700 . ?
C16 H16B 0.9700 . ?
C17 C18 1.378(4) . ?
C17 C22 1.383(4) . ?
C18 H18 0.9300 . ?
C18 C19 1.383(4) . ?
C19 H19 0.9300 . ?
C19 C20 1.372(5) . ?
C20 H20 0.9300 . ?
C20 C21 1.374(5) . ?
C21 H21 0.9300 . ?
C21 C22 1.380(4) . ?
C22 H22 0.9300 . ?
C23 H23 0.9800 . ?
C23 C24 1.501(4) . ?
C23 C30 1.405(4) . ?
C24 H24A 0.9700 . ?
C24 H24B 0.9700 . ?
C24 C25 1.506(5) . ?
C25 H25A 0.9700 . ?
C25 H25B 0.9700 . ?
C25 C26 1.515(5) . ?
C26 H26 0.9800 . ?
C26 C27 1.378(4) . ?
C27 H27 0.9800 . ?
C27 C28 1.502(4) . ?
C28 H28A 0.9700 . ?
C28 H28B 0.9700 . ?
C28 C29 1.520(5) . ?
C29 H29A 0.9700 . ?
C29 H29B 0.9700 . ?
C29 C30 1.513(4) . ?
C30 H30 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 Cl1 91.24(7) . . ?
C1 Rh1 C23 91.51(11) . . ?
C1 Rh1 C26 165.93(11) . . ?
C1 Rh1 C27 157.59(12) . . ?
C1 Rh1 C30 91.93(11) . . ?
C23 Rh1 Cl1 153.81(9) . . ?
C23 Rh1 C26 80.92(13) . . ?
C23 Rh1 C27 96.85(12) . . ?
C23 Rh1 C30 39.06(12) . . ?
C26 Rh1 Cl1 90.47(9) . . ?
C27 Rh1 Cl1 90.34(9) . . ?
C27 Rh1 C26 36.32(11) . . ?
C30 Rh1 Cl1 166.59(9) . . ?
C30 Rh1 C26 89.61(12) . . ?
C30 Rh1 C27 81.83(12) . . ?
C1 N1 C2 123.9(2) . . ?
C1 N1 C5 121.5(2) . . ?
C5 N1 C2 114.6(2) . . ?
C1 N2 C4 126.2(2) . . ?
C1 N2 C17 118.3(2) . . ?
C17 N2 C4 115.2(2) . . ?
N1 C1 Rh1 124.19(19) . . ?
N1 C1 N2 117.5(2) . . ?
N2 C1 Rh1 118.29(18) . . ?
N1 C2 H2 108.0 . . ?
N1 C2 C3 112.2(2) . . ?
N1 C2 C11 115.6(2) . . ?
C3 C2 H2 108.0 . . ?
C3 C2 C11 104.6(2) . . ?
C11 C2 H2 108.0 . . ?
C2 C3 C4 110.9(2) . . ?
C2 C3 C13 102.1(2) . . ?
C2 C3 C14 116.3(2) . . ?
C4 C3 C13 110.3(2) . . ?
C14 C3 C4 103.2(2) . . ?
C14 C3 C13 114.4(2) . . ?
N2 C4 C3 109.4(2) . . ?
N2 C4 H4 111.2 . . ?
N2 C4 C16 110.5(2) . . ?
C3 C4 H4 111.2 . . ?
C16 C4 C3 103.1(2) . . ?
C16 C4 H4 111.2 . . ?
C6 C5 N1 119.5(3) . . ?
C10 C5 N1 121.3(3) . . ?
C10 C5 C6 119.0(3) . . ?
C5 C6 H6 119.8 . . ?
C7 C6 C5 120.4(3) . . ?
C7 C6 H6 119.8 . . ?
C6 C7 H7 119.7 . . ?
C8 C7 C6 120.7(4) . . ?
C8 C7 H7 119.7 . . ?
C7 C8 H8 120.5 . . ?
C7 C8 C9 119.1(3) . . ?
C9 C8 H8 120.5 . . ?
C8 C9 H9 119.5 . . ?
C8 C9 C10 121.0(3) . . ?
C10 C9 H9 119.5 . . ?
C5 C10 C9 119.8(3) . . ?
C5 C10 H10 120.1 . . ?
C9 C10 H10 120.1 . . ?
C2 C11 H11A 110.7 . . ?
C2 C11 H11B 110.7 . . ?
C2 C11 C12 105.2(3) . . ?
H11A C11 H11B 108.8 . . ?
C12 C11 H11A 110.7 . . ?
C12 C11 H11B 110.7 . . ?
C11 C12 H12A 110.5 . . ?
C11 C12 H12B 110.5 . . ?
H12A C12 H12B 108.7 . . ?
C13 C12 C11 106.2(3) . . ?
C13 C12 H12A 110.5 . . ?
C13 C12 H12B 110.5 . . ?
C3 C13 H13A 110.5 . . ?
C3 C13 H13B 110.5 . . ?
C12 C13 C3 106.2(2) . . ?
C12 C13 H13A 110.5 . . ?
C12 C13 H13B 110.5 . . ?
H13A C13 H13B 108.7 . . ?
C3 C14 H14A 110.7 . . ?
C3 C14 H14B 110.7 . . ?
H14A C14 H14B 108.8 . . ?
C15 C14 C3 105.4(3) . . ?
C15 C14 H14A 110.7 . . ?
C15 C14 H14B 110.7 . . ?
C14 C15 H15A 110.1 . . ?
C14 C15 H15B 110.1 . . ?
H15A C15 H15B 108.4 . . ?
C16 C15 C14 108.0(3) . . ?
C16 C15 H15A 110.1 . . ?
C16 C15 H15B 110.1 . . ?
C4 C16 H16A 110.7 . . ?
C4 C16 H16B 110.7 . . ?
C15 C16 C4 105.4(3) . . ?
C15 C16 H16A 110.7 . . ?
C15 C16 H16B 110.7 . . ?
H16A C16 H16B 108.8 . . ?
C18 C17 N2 119.4(3) . . ?
C18 C17 C22 120.1(3) . . ?
C22 C17 N2 120.5(3) . . ?
C17 C18 H18 120.2 . . ?
C17 C18 C19 119.6(3) . . ?
C19 C18 H18 120.2 . . ?
C18 C19 H19 119.6 . . ?
C20 C19 C18 120.8(3) . . ?
C20 C19 H19 119.6 . . ?
C19 C20 H20 120.4 . . ?
C19 C20 C21 119.2(3) . . ?
C21 C20 H20 120.4 . . ?
C20 C21 H21 119.5 . . ?
C20 C21 C22 121.1(3) . . ?
C22 C21 H21 119.5 . . ?
C17 C22 H22 120.4 . . ?
C21 C22 C17 119.2(3) . . ?
C21 C22 H22 120.4 . . ?
Rh1 C23 H23 113.2 . . ?
C24 C23 Rh1 111.0(2) . . ?
C24 C23 H23 113.2 . . ?
C30 C23 Rh1 71.59(17) . . ?
C30 C23 H23 113.2 . . ?
C30 C23 C24 126.8(3) . . ?
C23 C24 H24A 108.8 . . ?
C23 C24 H24B 108.8 . . ?
C23 C24 C25 113.6(3) . . ?
H24A C24 H24B 107.7 . . ?
C25 C24 H24A 108.8 . . ?
C25 C24 H24B 108.8 . . ?
C24 C25 H25A 109.2 . . ?
C24 C25 H25B 109.2 . . ?
C24 C25 C26 112.1(3) . . ?
H25A C25 H25B 107.9 . . ?
C26 C25 H25A 109.2 . . ?
C26 C25 H25B 109.2 . . ?
Rh1 C26 H26 114.7 . . ?
C25 C26 Rh1 110.5(2) . . ?
C25 C26 H26 114.7 . . ?
C27 C26 Rh1 70.38(17) . . ?
C27 C26 C25 123.4(3) . . ?
C27 C26 H26 114.7 . . ?
Rh1 C27 H27 114.1 . . ?
C26 C27 Rh1 73.29(17) . . ?
C26 C27 H27 114.1 . . ?
C26 C27 C28 125.0(3) . . ?
C28 C27 Rh1 108.5(2) . . ?
C28 C27 H27 114.1 . . ?
C27 C28 H28A 108.6 . . ?
C27 C28 H28B 108.6 . . ?
C27 C28 C29 114.5(3) . . ?
H28A C28 H28B 107.6 . . ?
C29 C28 H28A 108.6 . . ?
C29 C28 H28B 108.6 . . ?
C28 C29 H29A 108.8 . . ?
C28 C29 H29B 108.8 . . ?
H29A C29 H29B 107.7 . . ?
C30 C29 C28 114.0(3) . . ?
C30 C29 H29A 108.8 . . ?
C30 C29 H29B 108.8 . . ?
Rh1 C30 H30 113.7 . . ?
C23 C30 Rh1 69.35(17) . . ?
C23 C30 C29 125.2(3) . . ?
C23 C30 H30 113.7 . . ?
C29 C30 Rh1 113.3(2) . . ?
C29 C30 H30 113.7 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
Rh1 C23 C24 C25 -38.5(4) . . . . ?
Rh1 C23 C30 C29 104.6(3) . . . . ?
Rh1 C26 C27 C28 -101.2(3) . . . . ?
Rh1 C27 C28 C29 -31.0(4) . . . . ?
N1 C2 C3 C4 48.6(3) . . . . ?
N1 C2 C3 C13 166.0(2) . . . . ?
N1 C2 C3 C14 -68.8(3) . . . . ?
N1 C2 C11 C12 -155.6(2) . . . . ?
N1 C5 C6 C7 -175.4(3) . . . . ?
N1 C5 C10 C9 175.2(2) . . . . ?
N2 C4 C16 C15 -83.2(4) . . . . ?
N2 C17 C18 C19 -179.5(3) . . . . ?
N2 C17 C22 C21 179.0(3) . . . . ?
C1 N1 C2 C3 -25.7(3) . . . . ?
C1 N1 C2 C11 94.1(3) . . . . ?
C1 N1 C5 C6 -117.8(3) . . . . ?
C1 N1 C5 C10 66.4(3) . . . . ?
C1 N2 C4 C3 23.0(4) . . . . ?
C1 N2 C4 C16 135.9(3) . . . . ?
C1 N2 C17 C18 110.3(3) . . . . ?
C1 N2 C17 C22 -71.7(4) . . . . ?
C2 N1 C1 Rh1 -179.89(18) . . . . ?
C2 N1 C1 N2 -0.2(4) . . . . ?
C2 N1 C5 C6 62.3(3) . . . . ?
C2 N1 C5 C10 -113.5(3) . . . . ?
C2 C3 C4 N2 -46.3(3) . . . . ?
C2 C3 C4 C16 -163.9(2) . . . . ?
C2 C3 C13 C12 -33.5(3) . . . . ?
C2 C3 C14 C15 151.1(3) . . . . ?
C2 C11 C12 C13 10.4(3) . . . . ?
C3 C2 C11 C12 -31.7(3) . . . . ?
C3 C4 C16 C15 33.6(4) . . . . ?
C3 C14 C15 C16 -9.0(5) . . . . ?
C4 N2 C1 Rh1 -179.0(2) . . . . ?
C4 N2 C1 N1 1.3(4) . . . . ?
C4 N2 C17 C18 -63.9(3) . . . . ?
C4 N2 C17 C22 114.1(3) . . . . ?
C4 C3 C13 C12 84.4(3) . . . . ?
C4 C3 C14 C15 29.6(4) . . . . ?
C5 N1 C1 Rh1 0.2(3) . . . . ?
C5 N1 C1 N2 179.9(2) . . . . ?
C5 N1 C2 C3 154.2(2) . . . . ?
C5 N1 C2 C11 -86.0(3) . . . . ?
C5 C6 C7 C8 -0.2(5) . . . . ?
C6 C5 C10 C9 -0.6(4) . . . . ?
C6 C7 C8 C9 -0.1(5) . . . . ?
C7 C8 C9 C10 0.0(5) . . . . ?
C8 C9 C10 C5 0.4(5) . . . . ?
C10 C5 C6 C7 0.5(5) . . . . ?
C11 C2 C3 C4 -77.5(3) . . . . ?
C11 C2 C3 C13 39.9(3) . . . . ?
C11 C2 C3 C14 165.1(3) . . . . ?
C11 C12 C13 C3 14.3(3) . . . . ?
C13 C3 C4 N2 -158.5(2) . . . . ?
C13 C3 C4 C16 83.8(3) . . . . ?
C13 C3 C14 C15 -90.2(4) . . . . ?
C14 C3 C4 N2 78.9(3) . . . . ?
C14 C3 C4 C16 -38.8(3) . . . . ?
C14 C3 C13 C12 -159.9(3) . . . . ?
C14 C15 C16 C4 -15.3(5) . . . . ?
C17 N2 C1 Rh1 7.5(3) . . . . ?
C17 N2 C1 N1 -172.2(2) . . . . ?
C17 N2 C4 C3 -163.3(2) . . . . ?
C17 N2 C4 C16 -50.4(3) . . . . ?
C17 C18 C19 C20 -0.5(5) . . . . ?
C18 C17 C22 C21 -3.1(5) . . . . ?
C18 C19 C20 C21 -1.0(6) . . . . ?
C19 C20 C21 C22 0.5(5) . . . . ?
C20 C21 C22 C17 1.6(5) . . . . ?
C22 C17 C18 C19 2.6(5) . . . . ?
C23 C24 C25 C26 34.7(4) . . . . ?
C24 C23 C30 Rh1 -102.9(3) . . . . ?
C24 C23 C30 C29 1.8(5) . . . . ?
C24 C25 C26 Rh1 -14.5(4) . . . . ?
C24 C25 C26 C27 -94.0(4) . . . . ?
C25 C26 C27 Rh1 102.2(3) . . . . ?
C25 C26 C27 C28 0.9(5) . . . . ?
C26 C27 C28 C29 51.3(5) . . . . ?
C27 C28 C29 C30 25.0(5) . . . . ?
C28 C29 C30 Rh1 -5.5(4) . . . . ?
C28 C29 C30 C23 -86.0(4) . . . . ?
C30 C23 C24 C25 43.8(5) . . . . ?

_database_code_depnum_ccdc_archive 'CCDC 973602'
