# Electronic Supplementary Material (ESI) for Chemical Science.
# 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.
#
#  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
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#  data retrieval see:
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#  from this site to visualise CIF-encoded structures and 
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data_c449a

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C46 H58 Cl6 N2'
_chemical_formula_weight         851.64

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           Monoclinic
_symmetry_space_group_name_H-M   P2(1)/c

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

_cell_length_a                   13.6043(18)
_cell_length_b                   29.340(4)
_cell_length_c                   11.7173(15)
_cell_angle_alpha                90.00
_cell_angle_beta                 101.006(3)
_cell_angle_gamma                90.00
_cell_volume                     4590.9(10)
_cell_formula_units_Z            4
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    931
_cell_measurement_theta_min      3.17
_cell_measurement_theta_max      26.43

_exptl_crystal_description       Block
_exptl_crystal_colour            Colourless
_exptl_crystal_size_max          0.51
_exptl_crystal_size_mid          0.50
_exptl_crystal_size_min          0.42
_exptl_crystal_density_meas      'Not Measured'
_exptl_crystal_density_diffrn    1.232
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1800
_exptl_absorpt_coefficient_mu    0.407
_exptl_absorpt_correction_type   Multi-scan
_exptl_absorpt_correction_T_min  0.6424
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_process_details   'Sadabs, (Sheldrick 2008)'

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            32323
_diffrn_reflns_av_R_equivalents  0.0324
_diffrn_reflns_av_sigmaI/netI    0.0391
_diffrn_reflns_limit_h_min       -17
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -37
_diffrn_reflns_limit_k_max       38
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_theta_min         1.39
_diffrn_reflns_theta_max         27.50
_reflns_number_total             10529
_reflns_number_gt                8377
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Bruker SMART'
_computing_cell_refinement       'Bruker SMART'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'

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

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0631P)²+2.2904P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         10529
_refine_ls_number_parameters     510
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0632
_refine_ls_R_factor_gt           0.0489
_refine_ls_wR_factor_ref         0.1279
_refine_ls_wR_factor_gt          0.1210
_refine_ls_goodness_of_fit_ref   1.049
_refine_ls_restrained_S_all      1.049
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
N1 N 0.58442(10) 0.07798(5) 1.09427(12) 0.0143(3) Uani 1 1 d . . .
H1N H 0.5642(16) 0.0626(7) 1.1473(19) 0.023(5) Uiso 1 1 d . . .
N2 N 0.27749(10) 0.11288(5) 0.80119(11) 0.0132(3) Uani 1 1 d . . .
H2N H 0.2304(17) 0.0960(8) 0.8176(19) 0.028(6) Uiso 1 1 d . . .
C1 C 0.52066(12) 0.09637(5) 0.99855(13) 0.0127(3) Uani 1 1 d . . .
C2 C 0.57758(12) 0.12645(5) 0.94178(14) 0.0136(3) Uani 1 1 d . . .
C3 C 0.53306(12) 0.14963(5) 0.84205(13) 0.0136(3) Uani 1 1 d . . .
H3 H 0.5704 0.1698 0.8032 0.016 Uiso 1 1 calc R . .
C4 C 0.43164(12) 0.14221(5) 0.80134(13) 0.0131(3) Uani 1 1 d . . .
C5 C 0.37603(12) 0.11278(5) 0.86103(13) 0.0129(3) Uani 1 1 d . . .
C6 C 0.41783(12) 0.08891(5) 0.96247(13) 0.0130(3) Uani 1 1 d . . .
C7 C 0.67797(12) 0.12721(5) 1.01051(14) 0.0144(3) Uani 1 1 d . . .
C8 C 0.76264(12) 0.15277(6) 1.00050(14) 0.0149(3) Uani 1 1 d . . .
H8 H 0.7607 0.1734 0.9376 0.018 Uiso 1 1 calc R . .
C9 C 0.84949(12) 0.14767(6) 1.08353(14) 0.0157(3) Uani 1 1 d . . .
C10 C 0.84972(12) 0.11525(6) 1.17249(14) 0.0164(3) Uani 1 1 d . . .
H10 H 0.9100 0.1114 1.2277 0.020 Uiso 1 1 calc R . .
C11 C 0.76802(12) 0.08848(5) 1.18530(13) 0.0145(3) Uani 1 1 d . . .
C12 C 0.67996(12) 0.09668(5) 1.10323(14) 0.0140(3) Uani 1 1 d . . .
C13 C 0.36248(12) 0.16062(5) 0.70328(13) 0.0131(3) Uani 1 1 d . . .
C14 C 0.37618(12) 0.19154(5) 0.61713(13) 0.0140(3) Uani 1 1 d . . .
H14 H 0.4401 0.2048 0.6182 0.017 Uiso 1 1 calc R . .
C15 C 0.29597(13) 0.20276(5) 0.53023(14) 0.0153(3) Uani 1 1 d . . .
C16 C 0.20149(12) 0.18377(6) 0.53537(14) 0.0160(3) Uani 1 1 d . . .
H16 H 0.1465 0.1921 0.4762 0.019 Uiso 1 1 calc R . .
C17 C 0.18318(12) 0.15371(5) 0.62098(13) 0.0138(3) Uani 1 1 d . . .
C18 C 0.26786(12) 0.14162(5) 0.70462(13) 0.0129(3) Uani 1 1 d . . .
C19 C 0.35767(12) 0.06007(5) 1.02779(13) 0.0133(3) Uani 1 1 d . . .
C20 C 0.39203(12) 0.01798(5) 1.07520(13) 0.0148(3) Uani 1 1 d . . .
H20 H 0.4563 0.0075 1.0665 0.018 Uiso 1 1 calc R . .
C21 C 0.33447(13) -0.00896(5) 1.13488(14) 0.0161(3) Uani 1 1 d . . .
H21 H 0.3601 -0.0374 1.1659 0.019 Uiso 1 1 calc R . .
C22 C 0.24012(13) 0.00497(6) 1.15003(14) 0.0168(3) Uani 1 1 d . . .
C23 C 0.20588(13) 0.04720(6) 1.10300(14) 0.0181(3) Uani 1 1 d . . .
H23 H 0.1416 0.0576 1.1118 0.022 Uiso 1 1 calc R . .
C24 C 0.26320(12) 0.07426(6) 1.04387(14) 0.0161(3) Uani 1 1 d . . .
H24 H 0.2378 0.1029 1.0138 0.019 Uiso 1 1 calc R . .
C25 C 0.94347(12) 0.17669(6) 1.08297(15) 0.0181(3) Uani 1 1 d . . .
C26 C 0.93459(14) 0.20517(6) 0.97207(16) 0.0236(4) Uani 1 1 d . . .
H26A H 0.9220 0.1850 0.9041 0.035 Uiso 1 1 calc R . .
H26B H 0.9970 0.2220 0.9734 0.035 Uiso 1 1 calc R . .
H26C H 0.8790 0.2268 0.9676 0.035 Uiso 1 1 calc R . .
C27 C 1.03643(13) 0.14617(6) 1.09221(19) 0.0269(4) Uani 1 1 d . . .
H27A H 1.0270 0.1249 1.0266 0.040 Uiso 1 1 calc R . .
H27B H 1.0462 0.1290 1.1652 0.040 Uiso 1 1 calc R . .
H27C H 1.0954 0.1652 1.0907 0.040 Uiso 1 1 calc R . .
C28 C 0.95810(15) 0.20944(7) 1.18748(17) 0.0260(4) Uani 1 1 d . . .
H28A H 1.0186 0.2277 1.1887 0.039 Uiso 1 1 calc R . .
H28B H 0.9650 0.1918 1.2596 0.039 Uiso 1 1 calc R . .
H28C H 0.8999 0.2297 1.1807 0.039 Uiso 1 1 calc R . .
C29 C 0.77296(12) 0.05260(5) 1.28154(14) 0.0157(3) Uani 1 1 d . . .
C30 C 0.87976(14) 0.04574(6) 1.34928(15) 0.0225(4) Uani 1 1 d . . .
H30A H 0.9234 0.0368 1.2955 0.034 Uiso 1 1 calc R . .
H30B H 0.8801 0.0218 1.4076 0.034 Uiso 1 1 calc R . .
H30C H 0.9042 0.0743 1.3881 0.034 Uiso 1 1 calc R . .
C31 C 0.73752(14) 0.00626(6) 1.22692(15) 0.0198(4) Uani 1 1 d . . .
H31A H 0.6680 0.0088 1.1856 0.030 Uiso 1 1 calc R . .
H31B H 0.7419 -0.0168 1.2883 0.030 Uiso 1 1 calc R . .
H31C H 0.7801 -0.0028 1.1721 0.030 Uiso 1 1 calc R . .
C32 C 0.70717(14) 0.06750(6) 1.36791(15) 0.0224(4) Uani 1 1 d . . .
H32A H 0.7319 0.0965 1.4038 0.034 Uiso 1 1 calc R . .
H32B H 0.7097 0.0442 1.4284 0.034 Uiso 1 1 calc R . .
H32C H 0.6379 0.0713 1.3266 0.034 Uiso 1 1 calc R . .
C33 C 0.30618(13) 0.23563(6) 0.43145(15) 0.0204(4) Uani 1 1 d . . .
C34 C 0.41508(14) 0.24713(7) 0.43052(16) 0.0254(4) Uani 1 1 d . . .
H34A H 0.4435 0.2641 0.5012 0.038 Uiso 1 1 calc R . .
H34B H 0.4189 0.2658 0.3622 0.038 Uiso 1 1 calc R . .
H34C H 0.4530 0.2189 0.4275 0.038 Uiso 1 1 calc R . .
C35 C 0.2630(2) 0.21386(10) 0.31333(18) 0.0492(7) Uani 1 1 d . . .
H35A H 0.2696 0.2352 0.2509 0.074 Uiso 1 1 calc R . .
H35B H 0.1920 0.2067 0.3096 0.074 Uiso 1 1 calc R . .
H35C H 0.2996 0.1858 0.3042 0.074 Uiso 1 1 calc R . .
C36 C 0.25002(19) 0.27968(8) 0.4470(2) 0.0484(7) Uani 1 1 d . . .
H36A H 0.2796 0.2938 0.5214 0.073 Uiso 1 1 calc R . .
H36B H 0.1794 0.2727 0.4459 0.073 Uiso 1 1 calc R . .
H36C H 0.2551 0.3008 0.3834 0.073 Uiso 1 1 calc R . .
C37 C 0.07800(12) 0.13546(6) 0.62400(14) 0.0155(3) Uani 1 1 d . . .
C38 C 0.07600(13) 0.08341(6) 0.61036(15) 0.0200(4) Uani 1 1 d . . .
H38A H 0.1213 0.0696 0.6764 0.030 Uiso 1 1 calc R . .
H38B H 0.0976 0.0752 0.5379 0.030 Uiso 1 1 calc R . .
H38C H 0.0078 0.0722 0.6081 0.030 Uiso 1 1 calc R . .
C39 C 0.04761(13) 0.14927(6) 0.73882(15) 0.0202(4) Uani 1 1 d . . .
H39A H -0.0195 0.1375 0.7406 0.030 Uiso 1 1 calc R . .
H39B H 0.0473 0.1826 0.7450 0.030 Uiso 1 1 calc R . .
H39C H 0.0956 0.1366 0.8041 0.030 Uiso 1 1 calc R . .
C40 C -0.00121(13) 0.15523(6) 0.52533(16) 0.0220(4) Uani 1 1 d . . .
H40A H -0.0673 0.1432 0.5311 0.033 Uiso 1 1 calc R . .
H40B H 0.0149 0.1466 0.4502 0.033 Uiso 1 1 calc R . .
H40C H -0.0017 0.1885 0.5317 0.033 Uiso 1 1 calc R . .
C41 C 0.17480(13) -0.02296(6) 1.21734(15) 0.0204(4) Uani 1 1 d . . .
C42 C 0.22542(16) -0.06755(7) 1.26410(18) 0.0301(4) Uani 1 1 d . . .
H42A H 0.2381 -0.0862 1.1991 0.045 Uiso 1 1 calc R . .
H42B H 0.1816 -0.0842 1.3069 0.045 Uiso 1 1 calc R . .
H42C H 0.2890 -0.0608 1.3163 0.045 Uiso 1 1 calc R . .
C43 C 0.15513(15) 0.00521(7) 1.32078(17) 0.0278(4) Uani 1 1 d . . .
H43A H 0.1120 -0.0121 1.3632 0.042 Uiso 1 1 calc R . .
H43B H 0.1220 0.0338 1.2925 0.042 Uiso 1 1 calc R . .
H43C H 0.2189 0.0119 1.3728 0.042 Uiso 1 1 calc R . .
C44 C 0.07510(16) -0.03417(8) 1.13639(18) 0.0359(5) Uani 1 1 d . . .
H44A H 0.0880 -0.0518 1.0698 0.054 Uiso 1 1 calc R . .
H44B H 0.0406 -0.0058 1.1088 0.054 Uiso 1 1 calc R . .
H44C H 0.0330 -0.0521 1.1789 0.054 Uiso 1 1 calc R . .
C1S C 0.66803(16) 0.20301(7) 0.24118(17) 0.0285(4) Uani 1 1 d . . .
H1S H 0.7101 0.1812 0.2058 0.034 Uiso 1 1 calc R . .
Cl1 Cl 0.40431(5) 0.07914(3) 0.34622(6) 0.0618(2) Uani 1 1 d . . .
Cl2 Cl 0.54903(4) 0.121277(19) 0.52689(4) 0.03422(13) Uani 1 1 d . . .
Cl3 Cl 0.43051(11) 0.04609(3) 0.58147(9) 0.1043(4) Uani 1 1 d . . .
C2S C 0.43264(18) 0.09399(7) 0.49411(19) 0.0352(5) Uani 1 1 d . . .
H2S H 0.3803 0.1158 0.5101 0.042 Uiso 1 1 calc R . .
Cl4 Cl 0.71694(6) 0.20677(3) 0.39099(5) 0.0630(2) Uani 1 1 d . . .
Cl5 Cl 0.54509(4) 0.182184(19) 0.21783(5) 0.03698(14) Uani 1 1 d . . .
Cl6 Cl 0.67310(5) 0.25654(2) 0.17507(6) 0.05058(18) 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
N1 C1 1.389(2) . ?
N1 C12 1.396(2) . ?
N2 C5 1.389(2) . ?
N2 C18 1.397(2) . ?
C1 C6 1.399(2) . ?
C1 C2 1.420(2) . ?
C2 C3 1.387(2) . ?
C2 C7 1.447(2) . ?
C3 C4 1.388(2) . ?
C4 C5 1.417(2) . ?
C4 C13 1.444(2) . ?
C5 C6 1.403(2) . ?
C6 C19 1.487(2) . ?
C7 C8 1.398(2) . ?
C7 C12 1.404(2) . ?
C8 C9 1.388(2) . ?
C9 C10 1.411(2) . ?
C9 C25 1.537(2) . ?
C10 C11 1.392(2) . ?
C11 C12 1.406(2) . ?
C11 C29 1.535(2) . ?
C13 C14 1.396(2) . ?
C13 C18 1.406(2) . ?
C14 C15 1.383(2) . ?
C15 C16 1.413(2) . ?
C15 C33 1.533(2) . ?
C16 C17 1.393(2) . ?
C17 C18 1.408(2) . ?
C17 C37 1.534(2) . ?
C19 C20 1.397(2) . ?
C19 C24 1.398(2) . ?
C20 C21 1.391(2) . ?
C21 C22 1.390(2) . ?
C22 C23 1.399(2) . ?
C22 C41 1.533(2) . ?
C23 C24 1.387(2) . ?
C25 C26 1.530(2) . ?
C25 C27 1.536(2) . ?
C25 C28 1.539(2) . ?
C29 C30 1.530(2) . ?
C29 C32 1.537(2) . ?
C29 C31 1.540(2) . ?
C33 C34 1.521(2) . ?
C33 C36 1.530(3) . ?
C33 C35 1.536(3) . ?
C37 C38 1.535(2) . ?
C37 C39 1.535(2) . ?
C37 C40 1.536(2) . ?
C41 C42 1.530(3) . ?
C41 C43 1.532(3) . ?
C41 C44 1.535(3) . ?
C1S Cl5 1.752(2) . ?
C1S Cl4 1.758(2) . ?
C1S Cl6 1.758(2) . ?
Cl1 C2S 1.757(2) . ?
Cl2 C2S 1.750(2) . ?
Cl3 C2S 1.742(2) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C1 N1 C12 109.70(13) . . ?
C5 N2 C18 110.02(13) . . ?
N1 C1 C6 128.13(14) . . ?
N1 C1 C2 107.88(14) . . ?
C6 C1 C2 123.97(14) . . ?
C3 C2 C1 120.64(15) . . ?
C3 C2 C7 132.45(15) . . ?
C1 C2 C7 106.86(14) . . ?
C2 C3 C4 117.25(15) . . ?
C3 C4 C5 121.01(14) . . ?
C3 C4 C13 131.96(15) . . ?
C5 C4 C13 107.00(14) . . ?
N2 C5 C6 128.65(15) . . ?
N2 C5 C4 107.71(13) . . ?
C6 C5 C4 123.64(15) . . ?
C1 C6 C5 113.45(14) . . ?
C1 C6 C19 123.39(14) . . ?
C5 C6 C19 123.11(14) . . ?
C8 C7 C12 120.83(15) . . ?
C8 C7 C2 131.82(15) . . ?
C12 C7 C2 107.30(14) . . ?
C9 C8 C7 119.22(15) . . ?
C8 C9 C10 118.18(15) . . ?
C8 C9 C25 122.33(15) . . ?
C10 C9 C25 119.48(14) . . ?
C11 C10 C9 124.81(15) . . ?
C10 C11 C12 115.02(15) . . ?
C10 C11 C29 122.84(14) . . ?
C12 C11 C29 122.13(15) . . ?
N1 C12 C7 108.20(14) . . ?
N1 C12 C11 130.05(15) . . ?
C7 C12 C11 121.75(15) . . ?
C14 C13 C18 120.99(14) . . ?
C14 C13 C4 131.45(15) . . ?
C18 C13 C4 107.57(14) . . ?
C15 C14 C13 119.45(15) . . ?
C14 C15 C16 118.12(15) . . ?
C14 C15 C33 122.22(15) . . ?
C16 C15 C33 119.64(14) . . ?
C17 C16 C15 124.71(15) . . ?
C16 C17 C18 115.19(15) . . ?
C16 C17 C37 122.21(14) . . ?
C18 C17 C37 122.60(14) . . ?
N2 C18 C13 107.69(14) . . ?
N2 C18 C17 130.81(15) . . ?
C13 C18 C17 121.45(14) . . ?
C20 C19 C24 117.14(15) . . ?
C20 C19 C6 122.16(15) . . ?
C24 C19 C6 120.71(14) . . ?
C21 C20 C19 121.61(15) . . ?
C22 C21 C20 121.27(15) . . ?
C21 C22 C23 117.13(15) . . ?
C21 C22 C41 123.26(15) . . ?
C23 C22 C41 119.59(15) . . ?
C24 C23 C22 121.80(16) . . ?
C23 C24 C19 121.05(15) . . ?
C26 C25 C27 107.98(15) . . ?
C26 C25 C9 112.03(14) . . ?
C27 C25 C9 110.54(14) . . ?
C26 C25 C28 108.18(15) . . ?
C27 C25 C28 109.15(15) . . ?
C9 C25 C28 108.88(14) . . ?
C30 C29 C11 112.05(14) . . ?
C30 C29 C32 108.09(14) . . ?
C11 C29 C32 109.84(13) . . ?
C30 C29 C31 106.88(14) . . ?
C11 C29 C31 109.50(13) . . ?
C32 C29 C31 110.44(14) . . ?
C34 C33 C36 108.83(17) . . ?
C34 C33 C15 111.93(14) . . ?
C36 C33 C15 108.82(15) . . ?
C34 C33 C35 106.95(16) . . ?
C36 C33 C35 110.15(19) . . ?
C15 C33 C35 110.14(16) . . ?
C17 C37 C38 110.04(14) . . ?
C17 C37 C39 109.66(13) . . ?
C38 C37 C39 110.56(14) . . ?
C17 C37 C40 111.99(13) . . ?
C38 C37 C40 107.54(14) . . ?
C39 C37 C40 107.00(14) . . ?
C42 C41 C43 108.21(15) . . ?
C42 C41 C22 112.06(15) . . ?
C43 C41 C22 108.94(15) . . ?
C42 C41 C44 108.80(16) . . ?
C43 C41 C44 109.71(17) . . ?
C22 C41 C44 109.10(14) . . ?
Cl5 C1S Cl4 110.23(11) . . ?
Cl5 C1S Cl6 111.05(11) . . ?
Cl4 C1S Cl6 110.16(11) . . ?
Cl3 C2S Cl2 110.84(14) . . ?
Cl3 C2S Cl1 110.77(12) . . ?
Cl2 C2S Cl1 110.41(12) . . ?

_diffrn_measured_fraction_theta_max 0.999
_diffrn_reflns_theta_full        27.50
_diffrn_measured_fraction_theta_full 0.999
_refine_diff_density_max         0.682
_refine_diff_density_min         -0.606
_refine_diff_density_rms         0.063
_database_code_depnum_ccdc_archive 'CCDC 1009378'
#######################################################################
#
#                 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_c262

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C42 H48 N2'
_chemical_formula_weight         580.82

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           Monoclinic
_symmetry_space_group_name_H-M   C2/c

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

_cell_length_a                   18.183(5)
_cell_length_b                   17.083(5)
_cell_length_c                   10.329(3)
_cell_angle_alpha                90.00
_cell_angle_beta                 97.513(5)
_cell_angle_gamma                90.00
_cell_volume                     3181.0(15)
_cell_formula_units_Z            4
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    1937
_cell_measurement_theta_min      2.26
_cell_measurement_theta_max      27.99

_exptl_crystal_description       Yellow
_exptl_crystal_colour            Red
_exptl_crystal_size_max          0.60
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.16
_exptl_crystal_density_meas      'Not Measured'
_exptl_crystal_density_diffrn    1.213
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1256
_exptl_absorpt_coefficient_mu    0.069
_exptl_absorpt_correction_type   Multi-scan
_exptl_absorpt_correction_T_min  0.6215
_exptl_absorpt_correction_T_max  0.7457
_exptl_absorpt_process_details   'Sadabs, (Sheldrick 2008)'

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            11189
_diffrn_reflns_av_R_equivalents  0.0416
_diffrn_reflns_av_sigmaI/netI    0.0459
_diffrn_reflns_limit_h_min       -23
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_k_min       -22
_diffrn_reflns_limit_k_max       22
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_theta_min         2.26
_diffrn_reflns_theta_max         27.50
_reflns_number_total             3649
_reflns_number_gt                2780
_reflns_threshold_expression     >2sigma(I)

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

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

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0608P)²+1.6016P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         3649
_refine_ls_number_parameters     210
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0676
_refine_ls_R_factor_gt           0.0488
_refine_ls_wR_factor_ref         0.1260
_refine_ls_wR_factor_gt          0.1163
_refine_ls_goodness_of_fit_ref   1.016
_refine_ls_restrained_S_all      1.016
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
N1 N 0.40269(7) -0.07531(7) 0.89568(12) 0.0155(3) Uani 1 1 d . . .
C1 C 0.5000 -0.09169(11) 0.7500 0.0145(4) Uani 1 2 d S . .
H1 H 0.5000 -0.1473 0.7500 0.017 Uiso 1 2 calc SR . .
C2 C 0.45479(8) -0.04822(8) 0.82047(14) 0.0149(3) Uani 1 1 d . . .
C3 C 0.45633(8) 0.03485(8) 0.82810(13) 0.0140(3) Uani 1 1 d . . .
C4 C 0.5000 0.07636(11) 0.7500 0.0135(4) Uani 1 2 d S . .
H4 H 0.5000 0.1320 0.7500 0.016 Uiso 1 2 calc SR . .
C5 C 0.37124(8) -0.01300(8) 0.95496(13) 0.0144(3) Uani 1 1 d . . .
C6 C 0.40492(7) 0.05634(8) 0.91865(13) 0.0142(3) Uani 1 1 d . . .
C7 C 0.38664(8) 0.12887(8) 0.97502(13) 0.0138(3) Uani 1 1 d . . .
C8 C 0.33163(8) 0.12749(8) 1.06084(13) 0.0150(3) Uani 1 1 d . . .
C9 C 0.29660(8) 0.05577(8) 1.08740(14) 0.0156(3) Uani 1 1 d . . .
H9 H 0.2587 0.0572 1.1425 0.019 Uiso 1 1 calc R . .
C10 C 0.31443(8) -0.01504(8) 1.03807(13) 0.0145(3) Uani 1 1 d . . .
C11 C 0.31307(8) 0.19802(9) 1.11916(14) 0.0179(3) Uani 1 1 d . . .
H11 H 0.2753 0.1978 1.1746 0.022 Uiso 1 1 calc R . .
C12 C 0.34807(8) 0.26685(8) 1.09788(14) 0.0182(3) Uani 1 1 d . . .
H12 H 0.3343 0.3134 1.1389 0.022 Uiso 1 1 calc R . .
C13 C 0.40436(8) 0.26970(8) 1.01588(13) 0.0149(3) Uani 1 1 d . . .
C14 C 0.42183(8) 0.20124(8) 0.95525(13) 0.0149(3) Uani 1 1 d . . .
H14 H 0.4588 0.2027 0.8982 0.018 Uiso 1 1 calc R . .
C15 C 0.27110(8) -0.08994(8) 1.06204(14) 0.0160(3) Uani 1 1 d . . .
C16 C 0.21731(9) -0.07629(9) 1.16260(15) 0.0215(3) Uani 1 1 d . . .
H16A H 0.1826 -0.0343 1.1320 0.032 Uiso 1 1 calc R . .
H16B H 0.2454 -0.0613 1.2464 0.032 Uiso 1 1 calc R . .
H16C H 0.1896 -0.1245 1.1736 0.032 Uiso 1 1 calc R . .
C17 C 0.32213(9) -0.15779(9) 1.11461(16) 0.0219(3) Uani 1 1 d . . .
H17A H 0.2919 -0.2018 1.1380 0.033 Uiso 1 1 calc R . .
H17B H 0.3549 -0.1403 1.1921 0.033 Uiso 1 1 calc R . .
H17C H 0.3521 -0.1744 1.0472 0.033 Uiso 1 1 calc R . .
C18 C 0.22512(8) -0.11351(9) 0.93254(14) 0.0203(3) Uani 1 1 d . . .
H18A H 0.1913 -0.0708 0.9019 0.030 Uiso 1 1 calc R . .
H18B H 0.1963 -0.1606 0.9459 0.030 Uiso 1 1 calc R . .
H18C H 0.2584 -0.1242 0.8673 0.030 Uiso 1 1 calc R . .
C19 C 0.44397(8) 0.34659(8) 0.99041(14) 0.0176(3) Uani 1 1 d . . .
C20 C 0.42314(9) 0.41344(9) 1.07824(16) 0.0232(3) Uani 1 1 d . . .
H20A H 0.3698 0.4238 1.0598 0.035 Uiso 1 1 calc R . .
H20B H 0.4507 0.4607 1.0609 0.035 Uiso 1 1 calc R . .
H20C H 0.4356 0.3984 1.1701 0.035 Uiso 1 1 calc R . .
C21 C 0.42040(9) 0.37069(9) 0.84752(15) 0.0230(3) Uani 1 1 d . . .
H21A H 0.4344 0.3295 0.7894 0.035 Uiso 1 1 calc R . .
H21B H 0.4452 0.4197 0.8295 0.035 Uiso 1 1 calc R . .
H21C H 0.3665 0.3783 0.8326 0.035 Uiso 1 1 calc R . .
C22 C 0.52823(9) 0.33495(9) 1.01504(17) 0.0248(4) Uani 1 1 d . . .
H22A H 0.5426 0.3173 1.1051 0.037 Uiso 1 1 calc R . .
H22B H 0.5531 0.3846 1.0013 0.037 Uiso 1 1 calc R . .
H22C H 0.5429 0.2955 0.9545 0.037 Uiso 1 1 calc R . .
H1N H 0.3929(11) -0.1256(13) 0.900(2) 0.041(6) Uiso 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
N1 C2 1.3811(19) . ?
N1 C5 1.3880(18) . ?
N1 H1N 0.88(2) . ?
C1 C2 1.3833(18) 2_656 ?
C1 C2 1.3833(18) . ?
C1 H1 0.9500 . ?
C2 C3 1.421(2) . ?
C3 C4 1.3970(17) . ?
C3 C6 1.453(2) . ?
C4 C3 1.3970(17) 2_656 ?
C4 H4 0.9500 . ?
C5 C6 1.4068(19) . ?
C5 C10 1.427(2) . ?
C6 C7 1.4267(19) . ?
C7 C8 1.421(2) . ?
C7 C14 1.419(2) . ?
C8 C11 1.408(2) . ?
C8 C9 1.424(2) . ?
C9 C10 1.368(2) . ?
C9 H9 0.9500 . ?
C10 C15 1.540(2) . ?
C11 C12 1.368(2) . ?
C11 H11 0.9500 . ?
C12 C13 1.412(2) . ?
C12 H12 0.9500 . ?
C13 C14 1.383(2) . ?
C13 C19 1.537(2) . ?
C14 H14 0.9500 . ?
C15 C16 1.535(2) . ?
C15 C18 1.536(2) . ?
C15 C17 1.539(2) . ?
C16 H16A 0.9800 . ?
C16 H16B 0.9800 . ?
C16 H16C 0.9800 . ?
C17 H17A 0.9800 . ?
C17 H17B 0.9800 . ?
C17 H17C 0.9800 . ?
C18 H18A 0.9800 . ?
C18 H18B 0.9800 . ?
C18 H18C 0.9800 . ?
C19 C22 1.533(2) . ?
C19 C21 1.538(2) . ?
C19 C20 1.536(2) . ?
C20 H20A 0.9800 . ?
C20 H20B 0.9800 . ?
C20 H20C 0.9800 . ?
C21 H21A 0.9800 . ?
C21 H21B 0.9800 . ?
C21 H21C 0.9800 . ?
C22 H22A 0.9800 . ?
C22 H22B 0.9800 . ?
C22 H22C 0.9800 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C2 N1 C5 110.09(12) . . ?
C2 N1 H1N 120.8(14) . . ?
C5 N1 H1N 129.1(14) . . ?
C2 C1 C2 115.06(18) 2_656 . ?
C2 C1 H1 122.5 2_656 . ?
C2 C1 H1 122.5 . . ?
C1 C2 N1 127.91(13) . . ?
C1 C2 C3 123.81(14) . . ?
N1 C2 C3 108.27(12) . . ?
C4 C3 C2 118.90(14) . . ?
C4 C3 C6 134.86(14) . . ?
C2 C3 C6 106.15(12) . . ?
C3 C4 C3 118.99(18) 2_656 . ?
C3 C4 H4 120.5 2_656 . ?
C3 C4 H4 120.5 . . ?
N1 C5 C6 108.02(12) . . ?
N1 C5 C10 128.24(13) . . ?
C6 C5 C10 123.73(13) . . ?
C5 C6 C7 119.33(13) . . ?
C5 C6 C3 107.33(12) . . ?
C7 C6 C3 133.30(13) . . ?
C8 C7 C14 118.15(12) . . ?
C8 C7 C6 117.43(12) . . ?
C14 C7 C6 124.36(13) . . ?
C11 C8 C7 118.72(13) . . ?
C11 C8 C9 121.04(13) . . ?
C7 C8 C9 120.24(13) . . ?
C10 C9 C8 123.74(13) . . ?
C10 C9 H9 118.1 . . ?
C8 C9 H9 118.1 . . ?
C9 C10 C5 115.33(13) . . ?
C9 C10 C15 121.59(13) . . ?
C5 C10 C15 122.88(12) . . ?
C12 C11 C8 121.61(13) . . ?
C12 C11 H11 119.2 . . ?
C8 C11 H11 119.2 . . ?
C11 C12 C13 120.98(13) . . ?
C11 C12 H12 119.5 . . ?
C13 C12 H12 119.5 . . ?
C14 C13 C12 118.02(13) . . ?
C14 C13 C19 120.30(13) . . ?
C12 C13 C19 121.65(12) . . ?
C13 C14 C7 122.47(13) . . ?
C13 C14 H14 118.8 . . ?
C7 C14 H14 118.8 . . ?
C16 C15 C18 107.87(12) . . ?
C16 C15 C10 111.55(12) . . ?
C18 C15 C10 108.04(11) . . ?
C16 C15 C17 106.49(12) . . ?
C18 C15 C17 110.14(12) . . ?
C10 C15 C17 112.65(12) . . ?
C15 C16 H16A 109.5 . . ?
C15 C16 H16B 109.5 . . ?
H16A C16 H16B 109.5 . . ?
C15 C16 H16C 109.5 . . ?
H16A C16 H16C 109.5 . . ?
H16B C16 H16C 109.5 . . ?
C15 C17 H17A 109.5 . . ?
C15 C17 H17B 109.5 . . ?
H17A C17 H17B 109.5 . . ?
C15 C17 H17C 109.5 . . ?
H17A C17 H17C 109.5 . . ?
H17B C17 H17C 109.5 . . ?
C15 C18 H18A 109.5 . . ?
C15 C18 H18B 109.5 . . ?
H18A C18 H18B 109.5 . . ?
C15 C18 H18C 109.5 . . ?
H18A C18 H18C 109.5 . . ?
H18B C18 H18C 109.5 . . ?
C22 C19 C21 109.94(13) . . ?
C22 C19 C20 108.46(12) . . ?
C21 C19 C20 107.96(13) . . ?
C22 C19 C13 109.95(12) . . ?
C21 C19 C13 108.36(12) . . ?
C20 C19 C13 112.14(12) . . ?
C19 C20 H20A 109.5 . . ?
C19 C20 H20B 109.5 . . ?
H20A C20 H20B 109.5 . . ?
C19 C20 H20C 109.5 . . ?
H20A C20 H20C 109.5 . . ?
H20B C20 H20C 109.5 . . ?
C19 C21 H21A 109.5 . . ?
C19 C21 H21B 109.5 . . ?
H21A C21 H21B 109.5 . . ?
C19 C21 H21C 109.5 . . ?
H21A C21 H21C 109.5 . . ?
H21B C21 H21C 109.5 . . ?
C19 C22 H22A 109.5 . . ?
C19 C22 H22B 109.5 . . ?
H22A C22 H22B 109.5 . . ?
C19 C22 H22C 109.5 . . ?
H22A C22 H22C 109.5 . . ?
H22B C22 H22C 109.5 . . ?

_diffrn_measured_fraction_theta_max 0.999
_diffrn_reflns_theta_full        27.50
_diffrn_measured_fraction_theta_full 0.999
_refine_diff_density_max         0.405
_refine_diff_density_min         -0.225
_refine_diff_density_rms         0.050
_database_code_depnum_ccdc_archive 'CCDC 1009379'
#######################################################################
#
#                 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_c322

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C66 H76 N2'
_chemical_formula_weight         897.29

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'

_symmetry_cell_setting           Monoclinic
_symmetry_space_group_name_H-M   C2/c

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

_cell_length_a                   25.799(6)
_cell_length_b                   18.171(4)
_cell_length_c                   11.441(3)
_cell_angle_alpha                90.00
_cell_angle_beta                 103.053(4)
_cell_angle_gamma                90.00
_cell_volume                     5225(2)
_cell_formula_units_Z            4
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    1358
_cell_measurement_theta_min      2.43
_cell_measurement_theta_max      21.15

_exptl_crystal_description       Block
_exptl_crystal_colour            Yellow
_exptl_crystal_size_max          0.50
_exptl_crystal_size_mid          0.30
_exptl_crystal_size_min          0.20
_exptl_crystal_density_meas      'Not Measured'
_exptl_crystal_density_diffrn    1.141
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1944
_exptl_absorpt_coefficient_mu    0.065
_exptl_absorpt_correction_type   Multi-scan
_exptl_absorpt_correction_T_min  0.5694
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_process_details   'Sadabs, (Sheldrick 2008)'

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         0
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            15119
_diffrn_reflns_av_R_equivalents  0.0838
_diffrn_reflns_av_sigmaI/netI    0.1000
_diffrn_reflns_limit_h_min       -25
_diffrn_reflns_limit_h_max       30
_diffrn_reflns_limit_k_min       -21
_diffrn_reflns_limit_k_max       21
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_theta_min         1.62
_diffrn_reflns_theta_max         24.99
_reflns_number_total             4603
_reflns_number_gt                2999
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'

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

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.1425P)²+3.1074P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         4603
_refine_ls_number_parameters     344
_refine_ls_number_restraints     108
_refine_ls_R_factor_all          0.1196
_refine_ls_R_factor_gt           0.0839
_refine_ls_wR_factor_ref         0.2628
_refine_ls_wR_factor_gt          0.2355
_refine_ls_goodness_of_fit_ref   1.048
_refine_ls_restrained_S_all      1.075
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
C23 C 0.5018(5) -0.05607(13) 0.2426(11) 0.0207(5) Uani 0.50 1 d PGU A -1
C24 C 0.5180(4) -0.0966(4) 0.3475(8) 0.028(2) Uani 0.50 1 d PGU A -1
H24 H 0.5274 -0.0721 0.4227 0.034 Uiso 0.50 1 calc PR A -1
C25 C 0.5205(3) -0.1729(4) 0.3424(6) 0.029(2) Uani 0.50 1 d PGU A -1
H25 H 0.5317 -0.2006 0.4142 0.035 Uiso 0.50 1 calc PR A -1
C26 C 0.5068(4) -0.20868(13) 0.2324(8) 0.034(3) Uani 0.50 1 d PGU A -1
C27 C 0.4906(4) -0.1682(4) 0.1275(6) 0.049(3) Uani 0.50 1 d PGU A -1
H27 H 0.4812 -0.1926 0.0523 0.059 Uiso 0.50 1 calc PR A -1
C28 C 0.4880(4) -0.0919(4) 0.1325(8) 0.038(3) Uani 0.50 1 d PGU A -1
H28 H 0.4769 -0.0642 0.0608 0.046 Uiso 0.50 1 calc PR A -1
C29 C 0.5076(4) -0.2949(4) 0.2214(7) 0.051(3) Uani 0.50 1 d PDU A -1
C30 C 0.5340(4) -0.3178(4) 0.1245(8) 0.081(3) Uani 0.50 1 d PDU A -1
H30A H 0.5719 -0.3053 0.1473 0.121 Uiso 0.50 1 calc PR A -1
H30B H 0.5175 -0.2921 0.0500 0.121 Uiso 0.50 1 calc PR A -1
H30C H 0.5300 -0.3710 0.1120 0.121 Uiso 0.50 1 calc PR A -1
C31 C 0.5339(5) -0.3296(7) 0.3414(8) 0.049(3) Uani 0.50 1 d PDU A -1
H31A H 0.5376 -0.3828 0.3309 0.074 Uiso 0.50 1 calc PR A -1
H31B H 0.5118 -0.3207 0.3993 0.074 Uiso 0.50 1 calc PR A -1
H31C H 0.5691 -0.3078 0.3711 0.074 Uiso 0.50 1 calc PR A -1
C32 C 0.4486(4) -0.3246(8) 0.1897(12) 0.063(4) Uani 0.50 1 d PDU A -1
H32A H 0.4295 -0.3032 0.1135 0.094 Uiso 0.50 1 calc PR A -1
H32B H 0.4307 -0.3106 0.2534 0.094 Uiso 0.50 1 calc PR A -1
H32C H 0.4489 -0.3783 0.1826 0.094 Uiso 0.50 1 calc PR A -1
N1 N 0.42044(10) 0.04346(14) 0.3360(2) 0.0236(6) Uani 1 1 d . . .
H1N H 0.4128(13) -0.0003(18) 0.340(3) 0.028 Uiso 1 1 d . . .
C1 C 0.5000 0.1863(2) 0.2500 0.0223(9) Uani 1 2 d S . .
H1 H 0.5000 0.2385 0.2500 0.027 Uiso 1 2 calc SR . .
C2 C 0.46004(10) 0.14709(15) 0.2885(3) 0.0208(7) Uani 1 1 d . . .
C3 C 0.46214(11) 0.06886(15) 0.2903(3) 0.0207(5) Uani 1 1 d . A .
C4 C 0.5000 0.0270(2) 0.2500 0.0207(5) Uani 1 2 d S . .
C5 C 0.41296(11) 0.16699(15) 0.3320(3) 0.0219(7) Uani 1 1 d . . .
C6 C 0.38855(11) 0.23641(17) 0.3469(3) 0.0255(7) Uani 1 1 d . . .
C7 C 0.40518(12) 0.30571(16) 0.3145(3) 0.0269(7) Uani 1 1 d . . .
H7 H 0.4358 0.3080 0.2817 0.032 Uiso 1 1 calc R . .
C8 C 0.37933(12) 0.37053(17) 0.3280(3) 0.0305(8) Uani 1 1 d . . .
C9 C 0.33482(14) 0.36615(19) 0.3792(3) 0.0401(9) Uani 1 1 d . . .
H9 H 0.3164 0.4100 0.3903 0.048 Uiso 1 1 calc R . .
C10 C 0.31748(13) 0.30059(19) 0.4132(3) 0.0413(9) Uani 1 1 d . . .
H10 H 0.2876 0.2998 0.4489 0.050 Uiso 1 1 calc R . .
C11 C 0.34273(12) 0.23335(17) 0.3967(3) 0.0311(8) Uani 1 1 d . . .
C12 C 0.32259(12) 0.16546(18) 0.4265(3) 0.0333(8) Uani 1 1 d . . .
H12 H 0.2924 0.1664 0.4611 0.040 Uiso 1 1 calc R . .
C13 C 0.34357(11) 0.09839(17) 0.4090(3) 0.0276(7) Uani 1 1 d . . .
C14 C 0.39018(11) 0.10136(16) 0.3604(3) 0.0244(7) Uani 1 1 d . . .
C15 C 0.39888(13) 0.44392(17) 0.2884(3) 0.0357(8) Uani 1 1 d . . .
C16 C 0.39938(17) 0.4401(2) 0.1555(4) 0.0521(10) Uani 1 1 d . . .
H16A H 0.4241 0.4016 0.1428 0.078 Uiso 1 1 calc R . .
H16B H 0.4108 0.4876 0.1295 0.078 Uiso 1 1 calc R . .
H16C H 0.3635 0.4286 0.1089 0.078 Uiso 1 1 calc R . .
C17 C 0.45473(15) 0.4586(2) 0.3625(4) 0.0498(10) Uani 1 1 d . . .
H17A H 0.4536 0.4644 0.4470 0.075 Uiso 1 1 calc R . .
H17B H 0.4686 0.5038 0.3340 0.075 Uiso 1 1 calc R . .
H17C H 0.4779 0.4172 0.3541 0.075 Uiso 1 1 calc R . .
C18 C 0.36351(16) 0.5090(2) 0.3052(4) 0.0566(12) Uani 1 1 d . . .
H18A H 0.3276 0.5017 0.2554 0.085 Uiso 1 1 calc R . .
H18B H 0.3785 0.5546 0.2811 0.085 Uiso 1 1 calc R . .
H18C H 0.3617 0.5124 0.3897 0.085 Uiso 1 1 calc R . .
C19 C 0.31946(12) 0.02591(18) 0.4399(3) 0.0307(8) Uani 1 1 d . . .
C20 C 0.26948(13) 0.0404(2) 0.4890(3) 0.0406(9) Uani 1 1 d . . .
H20A H 0.2791 0.0705 0.5618 0.061 Uiso 1 1 calc R . .
H20B H 0.2546 -0.0066 0.5080 0.061 Uiso 1 1 calc R . .
H20C H 0.2429 0.0666 0.4284 0.061 Uiso 1 1 calc R . .
C21 C 0.35978(14) -0.01502(19) 0.5367(3) 0.0381(9) Uani 1 1 d . . .
H21A H 0.3908 -0.0285 0.5052 0.057 Uiso 1 1 calc R . .
H21B H 0.3433 -0.0596 0.5600 0.057 Uiso 1 1 calc R . .
H21C H 0.3711 0.0169 0.6069 0.057 Uiso 1 1 calc R . .
C22 C 0.30181(14) -0.0212(2) 0.3265(3) 0.0406(9) Uani 1 1 d . . .
H22A H 0.2755 0.0061 0.2669 0.061 Uiso 1 1 calc R . .
H22B H 0.2859 -0.0670 0.3468 0.061 Uiso 1 1 calc R . .
H22C H 0.3327 -0.0326 0.2933 0.061 Uiso 1 1 calc R . .
C1S C 0.8088(3) 0.7863(3) 0.8996(7) 0.0940(19) Uani 1 1 d U . .
C2S C 0.8097(2) 0.7639(3) 0.7864(6) 0.0929(18) Uani 1 1 d U . .
H2S H 0.7846 0.7846 0.7209 0.111 Uiso 1 1 calc R . .
C3S C 0.8451(3) 0.7130(4) 0.7628(7) 0.103(2) Uani 1 1 d U . .
H3S H 0.8431 0.6986 0.6821 0.124 Uiso 1 1 calc R . .
C4S C 0.8821(3) 0.6832(4) 0.8495(10) 0.126(3) Uani 1 1 d U . .
H4S H 0.9070 0.6488 0.8320 0.151 Uiso 1 1 calc R . .
C5S C 0.8832(4) 0.7037(5) 0.9641(10) 0.149(4) Uani 1 1 d U . .
H5S H 0.9100 0.6843 1.0276 0.179 Uiso 1 1 calc R . .
C6S C 0.8452(4) 0.7533(4) 0.9911(6) 0.125(3) Uani 1 1 d U . .
H6S H 0.8449 0.7638 1.0723 0.150 Uiso 1 1 calc R . .
C7S C 0.7698(4) 0.8375(5) 0.9194(11) 0.184(4) Uani 1 1 d U . .
H7S1 H 0.7684 0.8794 0.8650 0.277 Uiso 1 1 calc R . .
H7S2 H 0.7793 0.8548 1.0027 0.277 Uiso 1 1 calc R . .
H7S3 H 0.7349 0.8134 0.9043 0.277 Uiso 1 1 calc R . .


_geom_special_details            
; 
 All esds (except the esd in the dihedral angle between two l.s. planes) 
 are estimated using the full covariance matrix.  The cell esds are taken 
 into account individually in the estimation of esds in distances, angles 
 and torsion angles; correlations between esds in cell parameters are only 
 used when they are defined by crystal symmetry.  An approximate (isotropic) 
 treatment of cell esds is used for estimating esds involving l.s. planes. 
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C23 C24 1.3900 . ?
C23 C28 1.3900 . ?
C23 C4 1.513(4) . ?
C24 C25 1.3900 . ?
C24 H24 0.9500 . ?
C25 C26 1.3900 . ?
C25 H25 0.9500 . ?
C26 C27 1.3900 . ?
C26 C29 1.573(7) . ?
C27 C28 1.3900 . ?
C27 H27 0.9500 . ?
C28 H28 0.9500 . ?
C29 C30 1.485(10) . ?
C29 C31 1.524(11) . ?
C29 C32 1.579(12) . ?
C30 H30A 0.9800 . ?
C30 H30B 0.9800 . ?
C30 H30C 0.9800 . ?
C31 H31A 0.9800 . ?
C31 H31B 0.9800 . ?
C31 H31C 0.9800 . ?
C32 H32A 0.9800 . ?
C32 H32B 0.9800 . ?
C32 H32C 0.9800 . ?
N1 C14 1.376(4) . ?
N1 C3 1.377(4) . ?
N1 H1N 0.82(3) . ?
C1 C2 1.403(3) 2_655 ?
C1 C2 1.403(3) . ?
C1 H1 0.9500 . ?
C2 C3 1.423(4) . ?
C2 C5 1.459(4) . ?
C3 C4 1.396(3) . ?
C4 C3 1.396(3) 2_655 ?
C4 C23 1.513(4) 2_655 ?
C5 C14 1.400(4) . ?
C5 C6 1.437(4) . ?
C6 C7 1.406(4) . ?
C6 C11 1.425(4) . ?
C7 C8 1.379(4) . ?
C7 H7 0.9500 . ?
C8 C9 1.404(5) . ?
C8 C15 1.530(5) . ?
C9 C10 1.360(5) . ?
C9 H9 0.9500 . ?
C10 C11 1.417(4) . ?
C10 H10 0.9500 . ?
C11 C12 1.410(4) . ?
C12 C13 1.367(4) . ?
C12 H12 0.9500 . ?
C13 C14 1.436(4) . ?
C13 C19 1.531(4) . ?
C15 C17 1.521(5) . ?
C15 C16 1.525(5) . ?
C15 C18 1.532(5) . ?
C16 H16A 0.9800 . ?
C16 H16B 0.9800 . ?
C16 H16C 0.9800 . ?
C17 H17A 0.9800 . ?
C17 H17B 0.9800 . ?
C17 H17C 0.9800 . ?
C18 H18A 0.9800 . ?
C18 H18B 0.9800 . ?
C18 H18C 0.9800 . ?
C19 C21 1.530(5) . ?
C19 C22 1.535(5) . ?
C19 C20 1.541(4) . ?
C20 H20A 0.9800 . ?
C20 H20B 0.9800 . ?
C20 H20C 0.9800 . ?
C21 H21A 0.9800 . ?
C21 H21B 0.9800 . ?
C21 H21C 0.9800 . ?
C22 H22A 0.9800 . ?
C22 H22B 0.9800 . ?
C22 H22C 0.9800 . ?
C1S C2S 1.362(9) . ?
C1S C6S 1.376(10) . ?
C1S C7S 1.425(9) . ?
C2S C3S 1.370(9) . ?
C2S H2S 0.9500 . ?
C3S C4S 1.326(10) . ?
C3S H3S 0.9500 . ?
C4S C5S 1.357(12) . ?
C4S H4S 0.9500 . ?
C5S C6S 1.416(12) . ?
C5S H5S 0.9500 . ?
C6S H6S 0.9500 . ?
C7S H7S1 0.9800 . ?
C7S H7S2 0.9800 . ?
C7S H7S3 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
C24 C23 C28 120.0 . . ?
C24 C23 C4 119.1(8) . . ?
C28 C23 C4 120.9(8) . . ?
C25 C24 C23 120.0 . . ?
C25 C24 H24 120.0 . . ?
C23 C24 H24 120.0 . . ?
C24 C25 C26 120.0 . . ?
C24 C25 H25 120.0 . . ?
C26 C25 H25 120.0 . . ?
C27 C26 C25 120.0 . . ?
C27 C26 C29 117.7(7) . . ?
C25 C26 C29 122.3(7) . . ?
C26 C27 C28 120.0 . . ?
C26 C27 H27 120.0 . . ?
C28 C27 H27 120.0 . . ?
C27 C28 C23 120.0 . . ?
C27 C28 H28 120.0 . . ?
C23 C28 H28 120.0 . . ?
C30 C29 C31 111.8(7) . . ?
C30 C29 C26 110.8(6) . . ?
C31 C29 C26 110.6(8) . . ?
C30 C29 C32 108.3(7) . . ?
C31 C29 C32 106.0(5) . . ?
C26 C29 C32 109.2(8) . . ?
C14 N1 C3 110.4(2) . . ?
C14 N1 H1N 125(2) . . ?
C3 N1 H1N 124(2) . . ?
C2 C1 C2 119.0(4) 2_655 . ?
C2 C1 H1 120.5 2_655 . ?
C2 C1 H1 120.5 . . ?
C1 C2 C3 118.9(3) . . ?
C1 C2 C5 135.2(3) . . ?
C3 C2 C5 105.9(2) . . ?
N1 C3 C4 127.4(3) . . ?
N1 C3 C2 108.1(2) . . ?
C4 C3 C2 124.5(3) . . ?
C3 C4 C3 113.9(3) 2_655 . ?
C3 C4 C23 126.5(4) 2_655 2_655 ?
C3 C4 C23 119.5(4) . 2_655 ?
C3 C4 C23 119.5(4) 2_655 . ?
C3 C4 C23 126.5(4) . . ?
C23 C4 C23 8.0(7) 2_655 . ?
C14 C5 C6 120.2(2) . . ?
C14 C5 C2 107.1(2) . . ?
C6 C5 C2 132.8(3) . . ?
C7 C6 C11 118.0(3) . . ?
C7 C6 C5 125.9(3) . . ?
C11 C6 C5 116.0(3) . . ?
C8 C7 C6 123.5(3) . . ?
C8 C7 H7 118.3 . . ?
C6 C7 H7 118.3 . . ?
C7 C8 C9 117.4(3) . . ?
C7 C8 C15 120.7(3) . . ?
C9 C8 C15 121.9(3) . . ?
C10 C9 C8 121.4(3) . . ?
C10 C9 H9 119.3 . . ?
C8 C9 H9 119.3 . . ?
C9 C10 C11 121.8(3) . . ?
C9 C10 H10 119.1 . . ?
C11 C10 H10 119.1 . . ?
C12 C11 C10 121.1(3) . . ?
C12 C11 C6 121.0(3) . . ?
C10 C11 C6 117.9(3) . . ?
C13 C12 C11 124.4(3) . . ?
C13 C12 H12 117.8 . . ?
C11 C12 H12 117.8 . . ?
C12 C13 C14 114.7(3) . . ?
C12 C13 C19 122.6(3) . . ?
C14 C13 C19 122.8(3) . . ?
N1 C14 C5 108.5(2) . . ?
N1 C14 C13 127.8(3) . . ?
C5 C14 C13 123.7(3) . . ?
C17 C15 C16 110.1(3) . . ?
C17 C15 C8 108.8(3) . . ?
C16 C15 C8 109.4(3) . . ?
C17 C15 C18 108.1(3) . . ?
C16 C15 C18 107.4(3) . . ?
C8 C15 C18 113.0(3) . . ?
C15 C16 H16A 109.5 . . ?
C15 C16 H16B 109.5 . . ?
H16A C16 H16B 109.5 . . ?
C15 C16 H16C 109.5 . . ?
H16A C16 H16C 109.5 . . ?
H16B C16 H16C 109.5 . . ?
C15 C17 H17A 109.5 . . ?
C15 C17 H17B 109.5 . . ?
H17A C17 H17B 109.5 . . ?
C15 C17 H17C 109.5 . . ?
H17A C17 H17C 109.5 . . ?
H17B C17 H17C 109.5 . . ?
C15 C18 H18A 109.5 . . ?
C15 C18 H18B 109.5 . . ?
H18A C18 H18B 109.5 . . ?
C15 C18 H18C 109.5 . . ?
H18A C18 H18C 109.5 . . ?
H18B C18 H18C 109.5 . . ?
C21 C19 C13 109.9(3) . . ?
C21 C19 C22 111.4(3) . . ?
C13 C19 C22 110.1(3) . . ?
C21 C19 C20 107.9(3) . . ?
C13 C19 C20 110.7(3) . . ?
C22 C19 C20 106.9(3) . . ?
C19 C20 H20A 109.5 . . ?
C19 C20 H20B 109.5 . . ?
H20A C20 H20B 109.5 . . ?
C19 C20 H20C 109.5 . . ?
H20A C20 H20C 109.5 . . ?
H20B C20 H20C 109.5 . . ?
C19 C21 H21A 109.5 . . ?
C19 C21 H21B 109.5 . . ?
H21A C21 H21B 109.5 . . ?
C19 C21 H21C 109.5 . . ?
H21A C21 H21C 109.5 . . ?
H21B C21 H21C 109.5 . . ?
C19 C22 H22A 109.5 . . ?
C19 C22 H22B 109.5 . . ?
H22A C22 H22B 109.5 . . ?
C19 C22 H22C 109.5 . . ?
H22A C22 H22C 109.5 . . ?
H22B C22 H22C 109.5 . . ?
C2S C1S C6S 116.0(6) . . ?
C2S C1S C7S 120.7(8) . . ?
C6S C1S C7S 123.3(8) . . ?
C1S C2S C3S 123.0(6) . . ?
C1S C2S H2S 118.5 . . ?
C3S C2S H2S 118.5 . . ?
C4S C3S C2S 121.9(7) . . ?
C4S C3S H3S 119.1 . . ?
C2S C3S H3S 119.1 . . ?
C3S C4S C5S 117.7(8) . . ?
C3S C4S H4S 121.1 . . ?
C5S C4S H4S 121.1 . . ?
C4S C5S C6S 121.4(7) . . ?
C4S C5S H5S 119.3 . . ?
C6S C5S H5S 119.3 . . ?
C1S C6S C5S 119.9(7) . . ?
C1S C6S H6S 120.0 . . ?
C5S C6S H6S 120.0 . . ?
C1S C7S H7S1 109.5 . . ?
C1S C7S H7S2 109.5 . . ?
H7S1 C7S H7S2 109.5 . . ?
C1S C7S H7S3 109.5 . . ?
H7S1 C7S H7S3 109.5 . . ?
H7S2 C7S H7S3 109.5 . . ?

_diffrn_measured_fraction_theta_max 1.000
_diffrn_reflns_theta_full        24.99
_diffrn_measured_fraction_theta_full 1.000
_refine_diff_density_max         0.652
_refine_diff_density_min         -0.504
_refine_diff_density_rms         0.068
_database_code_depnum_ccdc_archive 'CCDC 1009380'
