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

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#                                CCDC 
# 
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# 
#  This CIF contains data from an original supplementary publication
#  deposited with the CCDC, and may include chemical, crystal,
#  experimental, refinement, atomic coordinates,
#  anisotropic displacement parameters and molecular geometry data,
#  as required by the journal to which it was submitted.
#
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#  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_mo_dm13272_0m

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C48 H39 N O4'
_chemical_formula_weight         693.80

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           Orthorhombic
_symmetry_space_group_name_H-M   P2(1)2(1)2(1)

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

_cell_length_a                   11.0511(18)
_cell_length_b                   14.426(2)
_cell_length_c                   22.603(4)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_volume                     3603.5(10)
_cell_formula_units_Z            4
_cell_measurement_temperature    140(2)
_cell_measurement_reflns_used    2745
_cell_measurement_theta_min      2.29
_cell_measurement_theta_max      20.52

_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.23
_exptl_crystal_size_mid          0.13
_exptl_crystal_size_min          0.08
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.279
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1464
_exptl_absorpt_coefficient_mu    0.081
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.9817
_exptl_absorpt_correction_T_max  0.9936
_exptl_absorpt_process_details   sadabs

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      140(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            29121
_diffrn_reflns_av_R_equivalents  0.0943
_diffrn_reflns_av_sigmaI/netI    0.0969
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_l_min       -26
_diffrn_reflns_limit_l_max       29
_diffrn_reflns_theta_min         1.67
_diffrn_reflns_theta_max         27.48
_reflns_number_total             8265
_reflns_number_gt                5379
_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)+(0.0501P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   1.9(14)
_refine_ls_number_reflns         8265
_refine_ls_number_parameters     481
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1024
_refine_ls_R_factor_gt           0.0544
_refine_ls_wR_factor_ref         0.1184
_refine_ls_wR_factor_gt          0.1027
_refine_ls_goodness_of_fit_ref   0.975
_refine_ls_restrained_S_all      0.975
_refine_ls_shift/su_max          0.002
_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 0.9434(2) 0.57510(16) 0.24694(10) 0.0324(6) Uani 1 1 d . . .
O1 O 0.9354(2) 0.64656(15) 0.28182(9) 0.0463(6) Uani 1 1 d . . .
O2 O 0.65492(18) 0.56989(12) 0.20707(9) 0.0358(5) Uani 1 1 d . . .
O3 O 0.4414(2) 0.39643(15) 0.24338(11) 0.0525(6) Uani 1 1 d . . .
O4 O 0.44539(19) 0.29351(14) 0.17032(10) 0.0437(5) Uani 1 1 d . . .
C1 C 1.0039(3) 0.4965(2) 0.26769(14) 0.0432(8) Uani 1 1 d . . .
H1A H 1.0428 0.4988 0.3052 0.052 Uiso 1 1 calc R . .
C2 C 1.0086(3) 0.4179(2) 0.23602(16) 0.0442(9) Uani 1 1 d . . .
H2 H 1.0486 0.3651 0.2518 0.053 Uiso 1 1 calc R . .
C3 C 0.9547(3) 0.41259(18) 0.17952(14) 0.0336(7) Uani 1 1 d . . .
C4 C 0.9510(3) 0.3299(2) 0.14552(19) 0.0503(10) Uani 1 1 d . . .
H4 H 0.9853 0.2745 0.1607 0.060 Uiso 1 1 calc R . .
C5 C 0.8979(3) 0.3303(2) 0.09091(19) 0.0520(10) Uani 1 1 d . . .
H5 H 0.8946 0.2746 0.0685 0.062 Uiso 1 1 calc R . .
C6 C 0.8491(3) 0.4103(2) 0.06799(16) 0.0471(9) Uani 1 1 d . . .
H6 H 0.8154 0.4097 0.0293 0.057 Uiso 1 1 calc R . .
C7 C 0.8484(2) 0.49144(19) 0.10037(13) 0.0313(7) Uani 1 1 d . . .
H7 H 0.8132 0.5459 0.0842 0.038 Uiso 1 1 calc R . .
C8 C 0.8999(2) 0.49344(17) 0.15741(12) 0.0250(6) Uani 1 1 d . . .
C9 C 0.8957(2) 0.57532(17) 0.19246(12) 0.0228(6) Uani 1 1 d . . .
C10 C 0.8245(2) 0.65793(17) 0.17424(12) 0.0216(6) Uani 1 1 d . . .
C11 C 0.7011(2) 0.65096(17) 0.18318(13) 0.0281(7) Uani 1 1 d . . .
C12 C 0.6203(3) 0.72098(18) 0.16663(13) 0.0316(7) Uani 1 1 d . . .
H12 H 0.5358 0.7135 0.1728 0.038 Uiso 1 1 calc R . .
C13 C 0.6643(2) 0.80009(18) 0.14157(12) 0.0252(6) Uani 1 1 d . . .
H13 H 0.6100 0.8489 0.1320 0.030 Uiso 1 1 calc R . .
C14 C 0.7895(2) 0.81108(16) 0.12948(11) 0.0206(6) Uani 1 1 d . . .
C15 C 0.8305(2) 0.89084(17) 0.09807(11) 0.0189(5) Uani 1 1 d . . .
C16 C 0.9498(2) 0.89588(16) 0.07928(11) 0.0187(5) Uani 1 1 d . . .
C17 C 1.0338(2) 0.82642(16) 0.09708(11) 0.0177(5) Uani 1 1 d . . .
C18 C 0.9978(2) 0.75071(16) 0.13068(11) 0.0186(5) Uani 1 1 d . . .
C19 C 0.8729(2) 0.73921(17) 0.14581(11) 0.0191(5) Uani 1 1 d . . .
C20 C 0.6140(3) 0.5783(2) 0.26628(14) 0.0496(9) Uani 1 1 d . . .
H20A H 0.6821 0.5951 0.2919 0.074 Uiso 1 1 calc R . .
H20B H 0.5798 0.5191 0.2794 0.074 Uiso 1 1 calc R . .
H20C H 0.5517 0.6265 0.2685 0.074 Uiso 1 1 calc R . .
C21 C 0.7442(2) 0.96794(16) 0.08377(11) 0.0196(5) Uani 1 1 d . . .
C22 C 0.6960(2) 1.02278(17) 0.12819(12) 0.0262(6) Uani 1 1 d . . .
H22 H 0.7150 1.0099 0.1683 0.031 Uiso 1 1 calc R . .
C23 C 0.6204(2) 1.09628(18) 0.11451(14) 0.0303(7) Uani 1 1 d . . .
H23 H 0.5893 1.1343 0.1453 0.036 Uiso 1 1 calc R . .
C24 C 0.5898(2) 1.11460(19) 0.05634(14) 0.0307(7) Uani 1 1 d . . .
H24 H 0.5375 1.1648 0.0471 0.037 Uiso 1 1 calc R . .
C25 C 0.6355(2) 1.05986(19) 0.01220(13) 0.0302(7) Uani 1 1 d . . .
H25 H 0.6147 1.0722 -0.0278 0.036 Uiso 1 1 calc R . .
C26 C 0.7121(2) 0.98653(17) 0.02546(12) 0.0241(6) Uani 1 1 d . . .
H26 H 0.7427 0.9487 -0.0055 0.029 Uiso 1 1 calc R . .
C27 C 0.9894(2) 0.97112(16) 0.03755(12) 0.0203(6) Uani 1 1 d . . .
C28 C 1.0133(2) 1.06088(18) 0.05609(13) 0.0270(6) Uani 1 1 d . . .
H28 H 1.0080 1.0763 0.0969 0.032 Uiso 1 1 calc R . .
C29 C 1.0447(3) 1.12818(18) 0.01507(13) 0.0317(7) Uani 1 1 d . . .
H29 H 1.0613 1.1895 0.0280 0.038 Uiso 1 1 calc R . .
C30 C 1.0521(3) 1.1068(2) -0.04446(13) 0.0335(7) Uani 1 1 d . . .
H30 H 1.0718 1.1537 -0.0724 0.040 Uiso 1 1 calc R . .
C31 C 1.0310(3) 1.01749(19) -0.06323(13) 0.0325(7) Uani 1 1 d . . .
H31 H 1.0374 1.0024 -0.1040 0.039 Uiso 1 1 calc R . .
C32 C 1.0004(2) 0.94960(19) -0.02242(12) 0.0264(6) Uani 1 1 d . . .
H32 H 0.9866 0.8879 -0.0354 0.032 Uiso 1 1 calc R . .
C33 C 1.1642(2) 0.83826(17) 0.07998(11) 0.0193(5) Uani 1 1 d . . .
C34 C 1.2370(2) 0.9009(2) 0.10990(13) 0.0323(7) Uani 1 1 d . . .
H34 H 1.2047 0.9343 0.1425 0.039 Uiso 1 1 calc R . .
C35 C 1.3557(3) 0.9158(2) 0.09317(14) 0.0390(8) Uani 1 1 d . . .
H35 H 1.4044 0.9589 0.1143 0.047 Uiso 1 1 calc R . .
C36 C 1.4034(3) 0.8679(2) 0.04573(13) 0.0340(7) Uani 1 1 d . . .
H36 H 1.4850 0.8779 0.0342 0.041 Uiso 1 1 calc R . .
C37 C 1.3328(2) 0.80571(19) 0.01524(12) 0.0295(6) Uani 1 1 d . . .
H37 H 1.3656 0.7725 -0.0173 0.035 Uiso 1 1 calc R . .
C38 C 1.2129(2) 0.79152(18) 0.03215(12) 0.0255(6) Uani 1 1 d . . .
H38 H 1.1640 0.7492 0.0105 0.031 Uiso 1 1 calc R . .
C39 C 1.0953(2) 0.68523(16) 0.15096(11) 0.0190(6) Uani 1 1 d . . .
C40 C 1.1321(2) 0.61115(17) 0.11574(12) 0.0237(6) Uani 1 1 d . . .
H40 H 1.0911 0.5989 0.0796 0.028 Uiso 1 1 calc R . .
C41 C 1.2273(3) 0.55545(19) 0.13273(13) 0.0324(7) Uani 1 1 d . . .
H41 H 1.2515 0.5052 0.1083 0.039 Uiso 1 1 calc R . .
C42 C 1.2876(3) 0.5724(2) 0.18526(14) 0.0386(8) Uani 1 1 d . . .
H42 H 1.3532 0.5341 0.1970 0.046 Uiso 1 1 calc R . .
C43 C 1.2517(3) 0.6451(2) 0.22011(14) 0.0398(8) Uani 1 1 d . . .
H43 H 1.2924 0.6568 0.2564 0.048 Uiso 1 1 calc R . .
C44 C 1.1560(2) 0.70222(19) 0.20291(12) 0.0291(6) Uani 1 1 d . . .
H44 H 1.1328 0.7530 0.2272 0.035 Uiso 1 1 calc R . .
C45 C 0.6329(3) 0.3451(2) 0.20773(17) 0.0478(9) Uani 1 1 d . . .
H45A H 0.6642 0.4053 0.1946 0.072 Uiso 1 1 calc R . .
H45B H 0.6586 0.2969 0.1799 0.072 Uiso 1 1 calc R . .
H45C H 0.6646 0.3310 0.2472 0.072 Uiso 1 1 calc R . .
C46 C 0.4968(3) 0.3485(2) 0.20988(15) 0.0376(8) Uani 1 1 d . . .
C47 C 0.3133(3) 0.2959(2) 0.16738(16) 0.0464(9) Uani 1 1 d . . .
H47A H 0.2841 0.3608 0.1658 0.056 Uiso 1 1 calc R . .
H47B H 0.2777 0.2654 0.2025 0.056 Uiso 1 1 calc R . .
C48 C 0.2786(3) 0.2444(3) 0.11144(16) 0.0611(10) Uani 1 1 d . . .
H48A H 0.3151 0.2752 0.0772 0.092 Uiso 1 1 calc R . .
H48B H 0.1904 0.2443 0.1072 0.092 Uiso 1 1 calc R . .
H48C H 0.3080 0.1804 0.1138 0.092 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
N1 O1 1.301(3) . ?
N1 C9 1.340(3) . ?
N1 C1 1.397(4) . ?
O2 C11 1.386(3) . ?
O2 C20 1.418(4) . ?
O3 C46 1.194(3) . ?
O4 C46 1.324(4) . ?
O4 C47 1.462(4) . ?
C1 C2 1.342(4) . ?
C1 H1A 0.9500 . ?
C2 C3 1.411(5) . ?
C2 H2 0.9500 . ?
C3 C8 1.406(4) . ?
C3 C4 1.419(4) . ?
C4 C5 1.367(5) . ?
C4 H4 0.9500 . ?
C5 C6 1.374(5) . ?
C5 H5 0.9500 . ?
C6 C7 1.381(4) . ?
C6 H6 0.9500 . ?
C7 C8 1.409(4) . ?
C7 H7 0.9500 . ?
C8 C9 1.423(4) . ?
C9 C10 1.486(3) . ?
C10 C11 1.383(4) . ?
C10 C19 1.440(3) . ?
C11 C12 1.399(4) . ?
C12 C13 1.364(4) . ?
C12 H12 0.9500 . ?
C13 C14 1.419(3) . ?
C13 H13 0.9500 . ?
C14 C15 1.426(3) . ?
C14 C19 1.435(3) . ?
C15 C16 1.387(3) . ?
C15 C21 1.500(3) . ?
C16 C17 1.424(3) . ?
C16 C27 1.503(3) . ?
C17 C18 1.389(3) . ?
C17 C33 1.502(3) . ?
C18 C19 1.432(3) . ?
C18 C39 1.505(3) . ?
C20 H20A 0.9800 . ?
C20 H20B 0.9800 . ?
C20 H20C 0.9800 . ?
C21 C22 1.385(3) . ?
C21 C26 1.391(4) . ?
C22 C23 1.385(4) . ?
C22 H22 0.9500 . ?
C23 C24 1.383(4) . ?
C23 H23 0.9500 . ?
C24 C25 1.369(4) . ?
C24 H24 0.9500 . ?
C25 C26 1.387(4) . ?
C25 H25 0.9500 . ?
C26 H26 0.9500 . ?
C27 C28 1.386(4) . ?
C27 C32 1.396(4) . ?
C28 C29 1.387(4) . ?
C28 H28 0.9500 . ?
C29 C30 1.383(4) . ?
C29 H29 0.9500 . ?
C30 C31 1.376(4) . ?
C30 H30 0.9500 . ?
C31 C32 1.387(4) . ?
C31 H31 0.9500 . ?
C32 H32 0.9500 . ?
C33 C38 1.383(3) . ?
C33 C34 1.387(4) . ?
C34 C35 1.382(4) . ?
C34 H34 0.9500 . ?
C35 C36 1.380(4) . ?
C35 H35 0.9500 . ?
C36 C37 1.374(4) . ?
C36 H36 0.9500 . ?
C37 C38 1.394(4) . ?
C37 H37 0.9500 . ?
C38 H38 0.9500 . ?
C39 C44 1.375(4) . ?
C39 C40 1.393(3) . ?
C40 C41 1.379(4) . ?
C40 H40 0.9500 . ?
C41 C42 1.384(4) . ?
C41 H41 0.9500 . ?
C42 C43 1.370(4) . ?
C42 H42 0.9500 . ?
C43 C44 1.396(4) . ?
C43 H43 0.9500 . ?
C44 H44 0.9500 . ?
C45 C46 1.506(5) . ?
C45 H45A 0.9800 . ?
C45 H45B 0.9800 . ?
C45 H45C 0.9800 . ?
C47 C48 1.516(5) . ?
C47 H47A 0.9900 . ?
C47 H47B 0.9900 . ?
C48 H48A 0.9800 . ?
C48 H48B 0.9800 . ?
C48 H48C 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
O1 N1 C9 121.9(2) . . ?
O1 N1 C1 118.2(2) . . ?
C9 N1 C1 119.9(3) . . ?
C11 O2 C20 114.4(2) . . ?
C46 O4 C47 116.4(3) . . ?
C2 C1 N1 121.7(3) . . ?
C2 C1 H1A 119.2 . . ?
N1 C1 H1A 119.2 . . ?
C1 C2 C3 120.8(3) . . ?
C1 C2 H2 119.6 . . ?
C3 C2 H2 119.6 . . ?
C8 C3 C2 117.3(3) . . ?
C8 C3 C4 119.5(3) . . ?
C2 C3 C4 123.2(3) . . ?
C5 C4 C3 119.9(3) . . ?
C5 C4 H4 120.1 . . ?
C3 C4 H4 120.1 . . ?
C4 C5 C6 120.8(3) . . ?
C4 C5 H5 119.6 . . ?
C6 C5 H5 119.6 . . ?
C5 C6 C7 121.0(3) . . ?
C5 C6 H6 119.5 . . ?
C7 C6 H6 119.5 . . ?
C6 C7 C8 120.0(3) . . ?
C6 C7 H7 120.0 . . ?
C8 C7 H7 120.0 . . ?
C3 C8 C7 118.8(3) . . ?
C3 C8 C9 120.3(3) . . ?
C7 C8 C9 120.9(2) . . ?
N1 C9 C8 119.8(2) . . ?
N1 C9 C10 117.7(2) . . ?
C8 C9 C10 121.9(2) . . ?
C11 C10 C19 119.4(2) . . ?
C11 C10 C9 115.1(2) . . ?
C19 C10 C9 125.5(2) . . ?
C10 C11 O2 118.8(2) . . ?
C10 C11 C12 122.5(2) . . ?
O2 C11 C12 118.6(2) . . ?
C13 C12 C11 119.2(2) . . ?
C13 C12 H12 120.4 . . ?
C11 C12 H12 120.4 . . ?
C12 C13 C14 121.4(2) . . ?
C12 C13 H13 119.3 . . ?
C14 C13 H13 119.3 . . ?
C13 C14 C15 119.7(2) . . ?
C13 C14 C19 119.7(2) . . ?
C15 C14 C19 120.5(2) . . ?
C16 C15 C14 119.8(2) . . ?
C16 C15 C21 119.9(2) . . ?
C14 C15 C21 120.2(2) . . ?
C15 C16 C17 119.7(2) . . ?
C15 C16 C27 120.4(2) . . ?
C17 C16 C27 119.7(2) . . ?
C18 C17 C16 121.4(2) . . ?
C18 C17 C33 120.4(2) . . ?
C16 C17 C33 118.2(2) . . ?
C17 C18 C19 119.9(2) . . ?
C17 C18 C39 117.1(2) . . ?
C19 C18 C39 123.0(2) . . ?
C18 C19 C14 118.3(2) . . ?
C18 C19 C10 124.0(2) . . ?
C14 C19 C10 117.7(2) . . ?
O2 C20 H20A 109.5 . . ?
O2 C20 H20B 109.5 . . ?
H20A C20 H20B 109.5 . . ?
O2 C20 H20C 109.5 . . ?
H20A C20 H20C 109.5 . . ?
H20B C20 H20C 109.5 . . ?
C22 C21 C26 118.6(2) . . ?
C22 C21 C15 120.8(2) . . ?
C26 C21 C15 120.6(2) . . ?
C21 C22 C23 120.5(3) . . ?
C21 C22 H22 119.7 . . ?
C23 C22 H22 119.7 . . ?
C24 C23 C22 120.4(3) . . ?
C24 C23 H23 119.8 . . ?
C22 C23 H23 119.8 . . ?
C25 C24 C23 119.5(2) . . ?
C25 C24 H24 120.2 . . ?
C23 C24 H24 120.2 . . ?
C24 C25 C26 120.5(3) . . ?
C24 C25 H25 119.8 . . ?
C26 C25 H25 119.8 . . ?
C25 C26 C21 120.5(3) . . ?
C25 C26 H26 119.7 . . ?
C21 C26 H26 119.7 . . ?
C28 C27 C32 119.0(2) . . ?
C28 C27 C16 122.7(2) . . ?
C32 C27 C16 118.3(2) . . ?
C27 C28 C29 120.0(3) . . ?
C27 C28 H28 120.0 . . ?
C29 C28 H28 120.0 . . ?
C30 C29 C28 120.6(3) . . ?
C30 C29 H29 119.7 . . ?
C28 C29 H29 119.7 . . ?
C31 C30 C29 119.9(3) . . ?
C31 C30 H30 120.0 . . ?
C29 C30 H30 120.0 . . ?
C30 C31 C32 119.8(3) . . ?
C30 C31 H31 120.1 . . ?
C32 C31 H31 120.1 . . ?
C31 C32 C27 120.7(3) . . ?
C31 C32 H32 119.7 . . ?
C27 C32 H32 119.7 . . ?
C38 C33 C34 118.2(2) . . ?
C38 C33 C17 121.3(2) . . ?
C34 C33 C17 120.4(2) . . ?
C35 C34 C33 121.2(3) . . ?
C35 C34 H34 119.4 . . ?
C33 C34 H34 119.4 . . ?
C36 C35 C34 119.8(3) . . ?
C36 C35 H35 120.1 . . ?
C34 C35 H35 120.1 . . ?
C37 C36 C35 120.0(3) . . ?
C37 C36 H36 120.0 . . ?
C35 C36 H36 120.0 . . ?
C36 C37 C38 119.9(3) . . ?
C36 C37 H37 120.1 . . ?
C38 C37 H37 120.1 . . ?
C33 C38 C37 120.8(3) . . ?
C33 C38 H38 119.6 . . ?
C37 C38 H38 119.6 . . ?
C44 C39 C40 118.8(2) . . ?
C44 C39 C18 119.9(2) . . ?
C40 C39 C18 121.1(2) . . ?
C41 C40 C39 120.7(3) . . ?
C41 C40 H40 119.7 . . ?
C39 C40 H40 119.7 . . ?
C40 C41 C42 120.2(3) . . ?
C40 C41 H41 119.9 . . ?
C42 C41 H41 119.9 . . ?
C43 C42 C41 119.3(3) . . ?
C43 C42 H42 120.4 . . ?
C41 C42 H42 120.4 . . ?
C42 C43 C44 120.7(3) . . ?
C42 C43 H43 119.6 . . ?
C44 C43 H43 119.6 . . ?
C39 C44 C43 120.2(3) . . ?
C39 C44 H44 119.9 . . ?
C43 C44 H44 119.9 . . ?
C46 C45 H45A 109.5 . . ?
C46 C45 H45B 109.5 . . ?
H45A C45 H45B 109.5 . . ?
C46 C45 H45C 109.5 . . ?
H45A C45 H45C 109.5 . . ?
H45B C45 H45C 109.5 . . ?
O3 C46 O4 123.7(3) . . ?
O3 C46 C45 123.5(3) . . ?
O4 C46 C45 112.8(3) . . ?
O4 C47 C48 106.2(3) . . ?
O4 C47 H47A 110.5 . . ?
C48 C47 H47A 110.5 . . ?
O4 C47 H47B 110.5 . . ?
C48 C47 H47B 110.5 . . ?
H47A C47 H47B 108.7 . . ?
C47 C48 H48A 109.5 . . ?
C47 C48 H48B 109.5 . . ?
H48A C48 H48B 109.5 . . ?
C47 C48 H48C 109.5 . . ?
H48A C48 H48C 109.5 . . ?
H48B C48 H48C 109.5 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
O1 N1 C1 C2 175.2(3) . . . . ?
C9 N1 C1 C2 -4.8(4) . . . . ?
N1 C1 C2 C3 1.7(5) . . . . ?
C1 C2 C3 C8 1.9(4) . . . . ?
C1 C2 C3 C4 -176.4(3) . . . . ?
C8 C3 C4 C5 2.2(4) . . . . ?
C2 C3 C4 C5 -179.6(3) . . . . ?
C3 C4 C5 C6 0.8(5) . . . . ?
C4 C5 C6 C7 -2.5(5) . . . . ?
C5 C6 C7 C8 1.0(4) . . . . ?
C2 C3 C8 C7 178.1(2) . . . . ?
C4 C3 C8 C7 -3.5(4) . . . . ?
C2 C3 C8 C9 -2.5(4) . . . . ?
C4 C3 C8 C9 175.9(3) . . . . ?
C6 C7 C8 C3 2.0(4) . . . . ?
C6 C7 C8 C9 -177.4(3) . . . . ?
O1 N1 C9 C8 -175.9(2) . . . . ?
C1 N1 C9 C8 4.1(4) . . . . ?
O1 N1 C9 C10 -4.5(4) . . . . ?
C1 N1 C9 C10 175.6(2) . . . . ?
C3 C8 C9 N1 -0.5(4) . . . . ?
C7 C8 C9 N1 178.9(2) . . . . ?
C3 C8 C9 C10 -171.6(2) . . . . ?
C7 C8 C9 C10 7.8(4) . . . . ?
N1 C9 C10 C11 -94.1(3) . . . . ?
C8 C9 C10 C11 77.2(3) . . . . ?
N1 C9 C10 C19 89.7(3) . . . . ?
C8 C9 C10 C19 -99.1(3) . . . . ?
C19 C10 C11 O2 175.9(2) . . . . ?
C9 C10 C11 O2 -0.6(4) . . . . ?
C19 C10 C11 C12 -1.3(4) . . . . ?
C9 C10 C11 C12 -177.7(3) . . . . ?
C20 O2 C11 C10 108.1(3) . . . . ?
C20 O2 C11 C12 -74.7(4) . . . . ?
C10 C11 C12 C13 -1.1(5) . . . . ?
O2 C11 C12 C13 -178.2(3) . . . . ?
C11 C12 C13 C14 2.9(4) . . . . ?
C12 C13 C14 C15 173.9(2) . . . . ?
C12 C13 C14 C19 -2.3(4) . . . . ?
C13 C14 C15 C16 -171.4(2) . . . . ?
C19 C14 C15 C16 4.8(4) . . . . ?
C13 C14 C15 C21 6.8(4) . . . . ?
C19 C14 C15 C21 -176.9(2) . . . . ?
C14 C15 C16 C17 -7.0(4) . . . . ?
C21 C15 C16 C17 174.8(2) . . . . ?
C14 C15 C16 C27 169.6(2) . . . . ?
C21 C15 C16 C27 -8.6(3) . . . . ?
C15 C16 C17 C18 3.2(4) . . . . ?
C27 C16 C17 C18 -173.4(2) . . . . ?
C15 C16 C17 C33 -175.2(2) . . . . ?
C27 C16 C17 C33 8.3(3) . . . . ?
C16 C17 C18 C19 2.9(4) . . . . ?
C33 C17 C18 C19 -178.8(2) . . . . ?
C16 C17 C18 C39 -175.5(2) . . . . ?
C33 C17 C18 C39 2.8(3) . . . . ?
C17 C18 C19 C14 -4.9(3) . . . . ?
C39 C18 C19 C14 173.4(2) . . . . ?
C17 C18 C19 C10 172.3(2) . . . . ?
C39 C18 C19 C10 -9.4(4) . . . . ?
C13 C14 C19 C18 177.3(2) . . . . ?
C15 C14 C19 C18 1.1(3) . . . . ?
C13 C14 C19 C10 -0.1(3) . . . . ?
C15 C14 C19 C10 -176.3(2) . . . . ?
C11 C10 C19 C18 -175.5(3) . . . . ?
C9 C10 C19 C18 0.6(4) . . . . ?
C11 C10 C19 C14 1.8(4) . . . . ?
C9 C10 C19 C14 177.8(2) . . . . ?
C16 C15 C21 C22 -113.9(3) . . . . ?
C14 C15 C21 C22 67.8(3) . . . . ?
C16 C15 C21 C26 65.3(3) . . . . ?
C14 C15 C21 C26 -112.9(3) . . . . ?
C26 C21 C22 C23 -2.0(4) . . . . ?
C15 C21 C22 C23 177.3(2) . . . . ?
C21 C22 C23 C24 1.4(4) . . . . ?
C22 C23 C24 C25 -0.4(4) . . . . ?
C23 C24 C25 C26 -0.1(4) . . . . ?
C24 C25 C26 C21 -0.5(4) . . . . ?
C22 C21 C26 C25 1.5(4) . . . . ?
C15 C21 C26 C25 -177.8(2) . . . . ?
C15 C16 C27 C28 79.1(3) . . . . ?
C17 C16 C27 C28 -104.3(3) . . . . ?
C15 C16 C27 C32 -99.7(3) . . . . ?
C17 C16 C27 C32 76.9(3) . . . . ?
C32 C27 C28 C29 1.4(4) . . . . ?
C16 C27 C28 C29 -177.4(2) . . . . ?
C27 C28 C29 C30 0.3(4) . . . . ?
C28 C29 C30 C31 -1.6(4) . . . . ?
C29 C30 C31 C32 1.1(4) . . . . ?
C30 C31 C32 C27 0.7(4) . . . . ?
C28 C27 C32 C31 -1.9(4) . . . . ?
C16 C27 C32 C31 176.9(2) . . . . ?
C18 C17 C33 C38 81.7(3) . . . . ?
C16 C17 C33 C38 -100.0(3) . . . . ?
C18 C17 C33 C34 -102.2(3) . . . . ?
C16 C17 C33 C34 76.2(3) . . . . ?
C38 C33 C34 C35 -0.9(4) . . . . ?
C17 C33 C34 C35 -177.1(3) . . . . ?
C33 C34 C35 C36 0.2(5) . . . . ?
C34 C35 C36 C37 0.1(5) . . . . ?
C35 C36 C37 C38 0.3(4) . . . . ?
C34 C33 C38 C37 1.3(4) . . . . ?
C17 C33 C38 C37 177.5(2) . . . . ?
C36 C37 C38 C33 -1.0(4) . . . . ?
C17 C18 C39 C44 87.0(3) . . . . ?
C19 C18 C39 C44 -91.3(3) . . . . ?
C17 C18 C39 C40 -87.9(3) . . . . ?
C19 C18 C39 C40 93.8(3) . . . . ?
C44 C39 C40 C41 0.3(4) . . . . ?
C18 C39 C40 C41 175.3(2) . . . . ?
C39 C40 C41 C42 0.1(4) . . . . ?
C40 C41 C42 C43 0.0(4) . . . . ?
C41 C42 C43 C44 -0.5(4) . . . . ?
C40 C39 C44 C43 -0.9(4) . . . . ?
C18 C39 C44 C43 -175.9(2) . . . . ?
C42 C43 C44 C39 1.0(4) . . . . ?
C47 O4 C46 O3 2.2(4) . . . . ?
C47 O4 C46 C45 -177.1(3) . . . . ?
C46 O4 C47 C48 168.2(2) . . . . ?

_diffrn_measured_fraction_theta_max 0.999
_diffrn_reflns_theta_full        27.48
_diffrn_measured_fraction_theta_full 0.999
_refine_diff_density_max         0.219
_refine_diff_density_min         -0.228
_refine_diff_density_rms         0.049
_database_code_depnum_ccdc_archive 'CCDC 997510'
#######################################################################
#
#                 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_cd213199

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C47 H32 Cl N'
_chemical_formula_weight         646.19

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           Triclinic
_symmetry_space_group_name_H-M   P-1

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

_cell_length_a                   8.7922(9)
_cell_length_b                   9.5339(10)
_cell_length_c                   21.234(2)
_cell_angle_alpha                96.760(2)
_cell_angle_beta                 99.441(3)
_cell_angle_gamma                90.583(2)
_cell_volume                     1742.8(3)
_cell_formula_units_Z            2
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    1918
_cell_measurement_theta_min      4.699
_cell_measurement_theta_max      46.603

_exptl_crystal_description       prismatic
_exptl_crystal_colour            green
_exptl_crystal_size_max          0.211
_exptl_crystal_size_mid          0.148
_exptl_crystal_size_min          0.112
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.231
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             676
_exptl_absorpt_coefficient_mu    0.144
_exptl_absorpt_correction_type   empirical
_exptl_absorpt_correction_T_min  0.37002
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_process_details   sadabs

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      293(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            10628
_diffrn_reflns_av_R_equivalents  0.0275
_diffrn_reflns_av_sigmaI/netI    0.0590
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_limit_l_max       26
_diffrn_reflns_theta_min         1.96
_diffrn_reflns_theta_max         26.00
_reflns_number_total             6824
_reflns_number_gt                4369
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Bruker SMART'
_computing_cell_refinement       'Bruker SMART'
_computing_data_reduction        'Bruker SHELXTL'
_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)+(0.0627P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         6824
_refine_ls_number_parameters     446
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0842
_refine_ls_R_factor_gt           0.0511
_refine_ls_wR_factor_ref         0.1402
_refine_ls_wR_factor_gt          0.1238
_refine_ls_goodness_of_fit_ref   1.037
_refine_ls_restrained_S_all      1.039
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
Cl1 Cl 0.38740(7) 0.64699(6) 0.06981(3) 0.0646(2) Uani 1 1 d . . .
N1 N 0.3050(2) 0.35163(18) 0.07638(8) 0.0450(4) Uani 1 1 d D . .
C1 C 0.1647(2) 0.1707(2) 0.11045(10) 0.0424(5) Uani 1 1 d . . .
C2 C 0.0708(3) 0.1226(2) 0.15141(13) 0.0597(6) Uani 1 1 d . . .
H2 H 0.0412 0.1852 0.1839 0.072 Uiso 1 1 calc R . .
C3 C 0.0234(3) -0.0148(3) 0.14374(15) 0.0772(8) Uani 1 1 d . . .
H3 H -0.0392 -0.0462 0.1709 0.093 Uiso 1 1 calc R . .
C4 C 0.0680(3) -0.1098(3) 0.09524(16) 0.0802(9) Uani 1 1 d . . .
H4 H 0.0373 -0.2044 0.0915 0.096 Uiso 1 1 calc R . .
C5 C 0.1541(3) -0.0674(2) 0.05408(13) 0.0675(7) Uani 1 1 d . . .
H5 H 0.1806 -0.1321 0.0216 0.081 Uiso 1 1 calc R . .
C6 C 0.2048(2) 0.0756(2) 0.05984(11) 0.0513(6) Uani 1 1 d . . .
C7 C 0.2947(3) 0.1265(2) 0.01871(11) 0.0616(7) Uani 1 1 d . . .
H7 H 0.3227 0.0651 -0.0145 0.074 Uiso 1 1 calc R . .
C8 C 0.3418(3) 0.2639(2) 0.02642(10) 0.0572(6) Uani 1 1 d . . .
H8 H 0.3987 0.2977 -0.0022 0.069 Uiso 1 1 calc R . .
C9 C 0.2247(2) 0.3103(2) 0.11878(9) 0.0393(5) Uani 1 1 d . . .
C10 C 0.1995(2) 0.41956(19) 0.17207(9) 0.0380(5) Uani 1 1 d . . .
C11 C 0.0606(2) 0.4913(2) 0.16184(10) 0.0422(5) Uani 1 1 d . . .
C12 C -0.0560(2) 0.4564(2) 0.10691(11) 0.0524(6) Uani 1 1 d . . .
H12 H -0.0379 0.3873 0.0744 0.063 Uiso 1 1 calc R . .
C13 C -0.1923(3) 0.5217(2) 0.10114(12) 0.0589(6) Uani 1 1 d . . .
H13 H -0.2672 0.4958 0.0652 0.071 Uiso 1 1 calc R . .
C14 C -0.2223(3) 0.6279(2) 0.14856(12) 0.0592(6) Uani 1 1 d . . .
H14 H -0.3178 0.6700 0.1445 0.071 Uiso 1 1 calc R . .
C15 C -0.1135(2) 0.6694(2) 0.20017(11) 0.0532(6) Uani 1 1 d . . .
H15 H -0.1336 0.7423 0.2306 0.064 Uiso 1 1 calc R . .
C16 C 0.0320(2) 0.6032(2) 0.20874(10) 0.0423(5) Uani 1 1 d . . .
C17 C 0.1459(2) 0.6434(2) 0.26123(10) 0.0447(5) Uani 1 1 d . . .
H17 H 0.1285 0.7191 0.2908 0.054 Uiso 1 1 calc R . .
C18 C 0.2852(2) 0.57516(19) 0.27161(9) 0.0385(5) Uani 1 1 d . . .
C19 C 0.3117(2) 0.45457(19) 0.22792(9) 0.0364(4) Uani 1 1 d . . .
C20 C 0.4502(2) 0.37787(19) 0.24446(9) 0.0369(4) Uani 1 1 d . . .
C21 C 0.5576(2) 0.42607(19) 0.29735(9) 0.0387(5) Uani 1 1 d . . .
C22 C 0.5356(2) 0.5539(2) 0.33750(9) 0.0401(5) Uani 1 1 d . . .
C23 C 0.4014(2) 0.62441(19) 0.32588(9) 0.0401(5) Uani 1 1 d . . .
C24 C 0.3729(2) 0.7513(2) 0.36999(9) 0.0427(5) Uani 1 1 d . . .
C25 C 0.3813(3) 0.8858(2) 0.35325(12) 0.0631(6) Uani 1 1 d . . .
H25 H 0.4064 0.8993 0.3135 0.076 Uiso 1 1 calc R . .
C26 C 0.3530(3) 1.0004(3) 0.39479(17) 0.0804(9) Uani 1 1 d . . .
H26 H 0.3588 1.0906 0.3826 0.096 Uiso 1 1 calc R . .
C27 C 0.3168(3) 0.9848(3) 0.45307(16) 0.0844(10) Uani 1 1 d . . .
H27 H 0.2978 1.0631 0.4808 0.101 Uiso 1 1 calc R . .
C28 C 0.3087(3) 0.8524(4) 0.47040(13) 0.0842(9) Uani 1 1 d . . .
H28 H 0.2843 0.8403 0.5104 0.101 Uiso 1 1 calc R . .
C29 C 0.3363(3) 0.7365(3) 0.42934(11) 0.0635(6) Uani 1 1 d . . .
H29 H 0.3302 0.6467 0.4419 0.076 Uiso 1 1 calc R . .
C30 C 0.6636(2) 0.6090(2) 0.39042(9) 0.0445(5) Uani 1 1 d . . .
C31 C 0.7590(3) 0.7176(2) 0.38238(11) 0.0584(6) Uani 1 1 d . . .
H31 H 0.7395 0.7606 0.3449 0.070 Uiso 1 1 calc R . .
C32 C 0.8837(3) 0.7646(3) 0.42900(14) 0.0722(7) Uani 1 1 d . . .
H32 H 0.9480 0.8375 0.4224 0.087 Uiso 1 1 calc R . .
C33 C 0.9121(3) 0.7042(3) 0.48434(14) 0.0768(8) Uani 1 1 d . . .
H33 H 0.9965 0.7349 0.5156 0.092 Uiso 1 1 calc R . .
C34 C 0.8163(3) 0.5983(3) 0.49387(13) 0.0812(8) Uani 1 1 d . . .
H34 H 0.8341 0.5583 0.5322 0.097 Uiso 1 1 calc R . .
C35 C 0.6931(3) 0.5498(3) 0.44700(11) 0.0662(7) Uani 1 1 d . . .
H35 H 0.6294 0.4765 0.4538 0.079 Uiso 1 1 calc R . .
C36 C 0.7000(2) 0.3441(2) 0.31423(9) 0.0414(5) Uani 1 1 d . . .
C37 C 0.6929(3) 0.2194(2) 0.34046(11) 0.0557(6) Uani 1 1 d . . .
H37 H 0.5995 0.1873 0.3495 0.067 Uiso 1 1 calc R . .
C38 C 0.8236(3) 0.1413(3) 0.35356(13) 0.0751(8) Uani 1 1 d . . .
H38 H 0.8174 0.0572 0.3713 0.090 Uiso 1 1 calc R . .
C39 C 0.9610(3) 0.1869(3) 0.34074(14) 0.0787(8) Uani 1 1 d . . .
H39 H 1.0483 0.1333 0.3490 0.094 Uiso 1 1 calc R . .
C40 C 0.9703(3) 0.3112(3) 0.31576(13) 0.0725(7) Uani 1 1 d . . .
H40 H 1.0645 0.3432 0.3074 0.087 Uiso 1 1 calc R . .
C41 C 0.8408(2) 0.3897(2) 0.30275(11) 0.0564(6) Uani 1 1 d . . .
H41 H 0.8487 0.4748 0.2860 0.068 Uiso 1 1 calc R . .
C42 C 0.4853(2) 0.2420(2) 0.20713(9) 0.0412(5) Uani 1 1 d . . .
C43 C 0.4258(3) 0.1143(2) 0.21814(10) 0.0529(6) Uani 1 1 d . . .
H43 H 0.3560 0.1122 0.2466 0.064 Uiso 1 1 calc R . .
C44 C 0.4702(3) -0.0114(2) 0.18668(12) 0.0707(8) Uani 1 1 d . . .
H44 H 0.4291 -0.0975 0.1936 0.085 Uiso 1 1 calc R . .
C45 C 0.5742(4) -0.0080(3) 0.14574(14) 0.0798(9) Uani 1 1 d . . .
H45 H 0.6046 -0.0919 0.1250 0.096 Uiso 1 1 calc R . .
C46 C 0.6339(3) 0.1180(3) 0.13497(13) 0.0746(8) Uani 1 1 d . . .
H46 H 0.7043 0.1197 0.1068 0.090 Uiso 1 1 calc R . .
C47 C 0.5902(2) 0.2420(2) 0.16558(10) 0.0548(6) Uani 1 1 d . . .
H47 H 0.6320 0.3274 0.1582 0.066 Uiso 1 1 calc R . .
H1 H 0.338(3) 0.4465(18) 0.0798(12) 0.077(8) Uiso 1 1 d 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 C9 1.323(2) . ?
N1 C8 1.356(3) . ?
N1 H1 0.937(16) . ?
C1 C2 1.403(3) . ?
C1 C9 1.407(3) . ?
C1 C6 1.415(3) . ?
C2 C3 1.354(3) . ?
C2 H2 0.9300 . ?
C3 C4 1.398(4) . ?
C3 H3 0.9300 . ?
C4 C5 1.339(4) . ?
C4 H4 0.9300 . ?
C5 C6 1.415(3) . ?
C5 H5 0.9300 . ?
C6 C7 1.393(3) . ?
C7 C8 1.353(3) . ?
C7 H7 0.9300 . ?
C8 H8 0.9300 . ?
C9 C10 1.491(3) . ?
C10 C11 1.404(3) . ?
C10 C19 1.417(3) . ?
C11 C16 1.425(3) . ?
C11 C12 1.425(3) . ?
C12 C13 1.350(3) . ?
C12 H12 0.9300 . ?
C13 C14 1.400(3) . ?
C13 H13 0.9300 . ?
C14 C15 1.349(3) . ?
C14 H14 0.9300 . ?
C15 C16 1.426(3) . ?
C15 H15 0.9300 . ?
C16 C17 1.385(3) . ?
C17 C18 1.391(3) . ?
C17 H17 0.9300 . ?
C18 C19 1.436(3) . ?
C18 C23 1.438(3) . ?
C19 C20 1.442(3) . ?
C20 C21 1.374(2) . ?
C20 C42 1.499(3) . ?
C21 C22 1.437(3) . ?
C21 C36 1.498(3) . ?
C22 C23 1.365(3) . ?
C22 C30 1.496(3) . ?
C23 C24 1.490(3) . ?
C24 C29 1.373(3) . ?
C24 C25 1.375(3) . ?
C25 C26 1.373(3) . ?
C25 H25 0.9300 . ?
C26 C27 1.351(4) . ?
C26 H26 0.9300 . ?
C27 C28 1.359(4) . ?
C27 H27 0.9300 . ?
C28 C29 1.375(3) . ?
C28 H28 0.9300 . ?
C29 H29 0.9300 . ?
C30 C31 1.369(3) . ?
C30 C35 1.374(3) . ?
C31 C32 1.383(3) . ?
C31 H31 0.9300 . ?
C32 C33 1.357(4) . ?
C32 H32 0.9300 . ?
C33 C34 1.362(4) . ?
C33 H33 0.9300 . ?
C34 C35 1.381(3) . ?
C34 H34 0.9300 . ?
C35 H35 0.9300 . ?
C36 C37 1.376(3) . ?
C36 C41 1.377(3) . ?
C37 C38 1.383(3) . ?
C37 H37 0.9300 . ?
C38 C39 1.359(4) . ?
C38 H38 0.9300 . ?
C39 C40 1.361(4) . ?
C39 H39 0.9300 . ?
C40 C41 1.377(3) . ?
C40 H40 0.9300 . ?
C41 H41 0.9300 . ?
C42 C47 1.377(3) . ?
C42 C43 1.381(3) . ?
C43 C44 1.394(3) . ?
C43 H43 0.9300 . ?
C44 C45 1.364(4) . ?
C44 H44 0.9300 . ?
C45 C46 1.364(4) . ?
C45 H45 0.9300 . ?
C46 C47 1.370(3) . ?
C46 H46 0.9300 . ?
C47 H47 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
C9 N1 C8 123.49(19) . . ?
C9 N1 H1 119.6(15) . . ?
C8 N1 H1 116.9(15) . . ?
C2 C1 C9 122.32(19) . . ?
C2 C1 C6 119.46(19) . . ?
C9 C1 C6 118.2(2) . . ?
C3 C2 C1 120.1(2) . . ?
C3 C2 H2 119.9 . . ?
C1 C2 H2 119.9 . . ?
C2 C3 C4 120.3(3) . . ?
C2 C3 H3 119.8 . . ?
C4 C3 H3 119.8 . . ?
C5 C4 C3 121.4(2) . . ?
C5 C4 H4 119.3 . . ?
C3 C4 H4 119.3 . . ?
C4 C5 C6 120.2(2) . . ?
C4 C5 H5 119.9 . . ?
C6 C5 H5 119.9 . . ?
C7 C6 C5 123.1(2) . . ?
C7 C6 C1 118.47(19) . . ?
C5 C6 C1 118.5(2) . . ?
C8 C7 C6 121.0(2) . . ?
C8 C7 H7 119.5 . . ?
C6 C7 H7 119.5 . . ?
C7 C8 N1 119.1(2) . . ?
C7 C8 H8 120.4 . . ?
N1 C8 H8 120.4 . . ?
N1 C9 C1 119.46(18) . . ?
N1 C9 C10 116.42(17) . . ?
C1 C9 C10 124.10(18) . . ?
C11 C10 C19 121.90(17) . . ?
C11 C10 C9 115.63(16) . . ?
C19 C10 C9 122.38(16) . . ?
C10 C11 C16 119.11(17) . . ?
C10 C11 C12 123.19(18) . . ?
C16 C11 C12 117.70(18) . . ?
C13 C12 C11 121.2(2) . . ?
C13 C12 H12 119.4 . . ?
C11 C12 H12 119.4 . . ?
C12 C13 C14 120.9(2) . . ?
C12 C13 H13 119.6 . . ?
C14 C13 H13 119.6 . . ?
C15 C14 C13 120.4(2) . . ?
C15 C14 H14 119.8 . . ?
C13 C14 H14 119.8 . . ?
C14 C15 C16 120.9(2) . . ?
C14 C15 H15 119.5 . . ?
C16 C15 H15 119.5 . . ?
C17 C16 C11 118.90(17) . . ?
C17 C16 C15 122.28(19) . . ?
C11 C16 C15 118.82(18) . . ?
C16 C17 C18 122.73(18) . . ?
C16 C17 H17 118.6 . . ?
C18 C17 H17 118.6 . . ?
C17 C18 C19 119.42(17) . . ?
C17 C18 C23 120.28(17) . . ?
C19 C18 C23 120.30(16) . . ?
C10 C19 C18 117.58(16) . . ?
C10 C19 C20 125.00(16) . . ?
C18 C19 C20 117.43(16) . . ?
C21 C20 C19 120.64(16) . . ?
C21 C20 C42 115.98(16) . . ?
C19 C20 C42 123.37(16) . . ?
C20 C21 C22 121.12(16) . . ?
C20 C21 C36 119.90(16) . . ?
C22 C21 C36 118.98(16) . . ?
C23 C22 C21 119.91(17) . . ?
C23 C22 C30 121.40(17) . . ?
C21 C22 C30 118.67(16) . . ?
C22 C23 C18 120.22(17) . . ?
C22 C23 C24 120.30(17) . . ?
C18 C23 C24 119.47(16) . . ?
C29 C24 C25 117.8(2) . . ?
C29 C24 C23 120.24(19) . . ?
C25 C24 C23 122.00(19) . . ?
C26 C25 C24 120.5(3) . . ?
C26 C25 H25 119.7 . . ?
C24 C25 H25 119.7 . . ?
C27 C26 C25 121.3(3) . . ?
C27 C26 H26 119.4 . . ?
C25 C26 H26 119.4 . . ?
C26 C27 C28 118.8(3) . . ?
C26 C27 H27 120.6 . . ?
C28 C27 H27 120.6 . . ?
C27 C28 C29 120.7(3) . . ?
C27 C28 H28 119.7 . . ?
C29 C28 H28 119.7 . . ?
C24 C29 C28 120.9(3) . . ?
C24 C29 H29 119.5 . . ?
C28 C29 H29 119.5 . . ?
C31 C30 C35 118.1(2) . . ?
C31 C30 C22 120.16(19) . . ?
C35 C30 C22 121.7(2) . . ?
C30 C31 C32 121.2(2) . . ?
C30 C31 H31 119.4 . . ?
C32 C31 H31 119.4 . . ?
C33 C32 C31 120.0(3) . . ?
C33 C32 H32 120.0 . . ?
C31 C32 H32 120.0 . . ?
C32 C33 C34 119.6(2) . . ?
C32 C33 H33 120.2 . . ?
C34 C33 H33 120.2 . . ?
C33 C34 C35 120.5(2) . . ?
C33 C34 H34 119.8 . . ?
C35 C34 H34 119.8 . . ?
C30 C35 C34 120.6(2) . . ?
C30 C35 H35 119.7 . . ?
C34 C35 H35 119.7 . . ?
C37 C36 C41 118.1(2) . . ?
C37 C36 C21 120.81(19) . . ?
C41 C36 C21 121.07(19) . . ?
C36 C37 C38 120.5(2) . . ?
C36 C37 H37 119.7 . . ?
C38 C37 H37 119.7 . . ?
C39 C38 C37 120.4(2) . . ?
C39 C38 H38 119.8 . . ?
C37 C38 H38 119.8 . . ?
C38 C39 C40 119.7(2) . . ?
C38 C39 H39 120.2 . . ?
C40 C39 H39 120.2 . . ?
C39 C40 C41 120.2(3) . . ?
C39 C40 H40 119.9 . . ?
C41 C40 H40 119.9 . . ?
C36 C41 C40 121.0(2) . . ?
C36 C41 H41 119.5 . . ?
C40 C41 H41 119.5 . . ?
C47 C42 C43 118.78(19) . . ?
C47 C42 C20 119.83(19) . . ?
C43 C42 C20 121.09(19) . . ?
C42 C43 C44 120.0(2) . . ?
C42 C43 H43 120.0 . . ?
C44 C43 H43 120.0 . . ?
C45 C44 C43 119.8(2) . . ?
C45 C44 H44 120.1 . . ?
C43 C44 H44 120.1 . . ?
C44 C45 C46 120.3(2) . . ?
C44 C45 H45 119.8 . . ?
C46 C45 H45 119.8 . . ?
C45 C46 C47 120.1(3) . . ?
C45 C46 H46 119.9 . . ?
C47 C46 H46 119.9 . . ?
C46 C47 C42 120.9(2) . . ?
C46 C47 H47 119.5 . . ?
C42 C47 H47 119.5 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C9 C1 C2 C3 -176.1(2) . . . . ?
C6 C1 C2 C3 2.1(3) . . . . ?
C1 C2 C3 C4 0.3(4) . . . . ?
C2 C3 C4 C5 -2.1(4) . . . . ?
C3 C4 C5 C6 1.4(4) . . . . ?
C4 C5 C6 C7 179.9(2) . . . . ?
C4 C5 C6 C1 1.1(3) . . . . ?
C2 C1 C6 C7 178.29(19) . . . . ?
C9 C1 C6 C7 -3.4(3) . . . . ?
C2 C1 C6 C5 -2.8(3) . . . . ?
C9 C1 C6 C5 175.50(18) . . . . ?
C5 C6 C7 C8 -179.4(2) . . . . ?
C1 C6 C7 C8 -0.5(3) . . . . ?
C6 C7 C8 N1 2.3(3) . . . . ?
C9 N1 C8 C7 0.1(3) . . . . ?
C8 N1 C9 C1 -4.1(3) . . . . ?
C8 N1 C9 C10 177.84(18) . . . . ?
C2 C1 C9 N1 -176.05(19) . . . . ?
C6 C1 C9 N1 5.7(3) . . . . ?
C2 C1 C9 C10 1.8(3) . . . . ?
C6 C1 C9 C10 -176.47(17) . . . . ?
N1 C9 C10 C11 94.3(2) . . . . ?
C1 C9 C10 C11 -83.6(2) . . . . ?
N1 C9 C10 C19 -82.3(2) . . . . ?
C1 C9 C10 C19 99.8(2) . . . . ?
C19 C10 C11 C16 0.4(3) . . . . ?
C9 C10 C11 C16 -176.20(17) . . . . ?
C19 C10 C11 C12 -178.49(19) . . . . ?
C9 C10 C11 C12 4.9(3) . . . . ?
C10 C11 C12 C13 175.4(2) . . . . ?
C16 C11 C12 C13 -3.6(3) . . . . ?
C11 C12 C13 C14 1.2(3) . . . . ?
C12 C13 C14 C15 1.8(4) . . . . ?
C13 C14 C15 C16 -2.2(3) . . . . ?
C10 C11 C16 C17 3.7(3) . . . . ?
C12 C11 C16 C17 -177.31(18) . . . . ?
C10 C11 C16 C15 -175.88(18) . . . . ?
C12 C11 C16 C15 3.1(3) . . . . ?
C14 C15 C16 C17 -179.9(2) . . . . ?
C14 C15 C16 C11 -0.3(3) . . . . ?
C11 C16 C17 C18 -2.7(3) . . . . ?
C15 C16 C17 C18 176.9(2) . . . . ?
C16 C17 C18 C19 -2.5(3) . . . . ?
C16 C17 C18 C23 177.95(18) . . . . ?
C11 C10 C19 C18 -5.4(3) . . . . ?
C9 C10 C19 C18 170.96(17) . . . . ?
C11 C10 C19 C20 174.18(18) . . . . ?
C9 C10 C19 C20 -9.4(3) . . . . ?
C17 C18 C19 C10 6.4(3) . . . . ?
C23 C18 C19 C10 -174.01(17) . . . . ?
C17 C18 C19 C20 -173.24(18) . . . . ?
C23 C18 C19 C20 6.3(3) . . . . ?
C10 C19 C20 C21 175.24(18) . . . . ?
C18 C19 C20 C21 -5.1(3) . . . . ?
C10 C19 C20 C42 -6.0(3) . . . . ?
C18 C19 C20 C42 173.67(18) . . . . ?
C19 C20 C21 C22 -0.2(3) . . . . ?
C42 C20 C21 C22 -179.05(17) . . . . ?
C19 C20 C21 C36 179.32(17) . . . . ?
C42 C20 C21 C36 0.4(3) . . . . ?
C20 C21 C22 C23 4.5(3) . . . . ?
C36 C21 C22 C23 -174.99(18) . . . . ?
C20 C21 C22 C30 -173.85(18) . . . . ?
C36 C21 C22 C30 6.7(3) . . . . ?
C21 C22 C23 C18 -3.2(3) . . . . ?
C30 C22 C23 C18 175.08(18) . . . . ?
C21 C22 C23 C24 175.64(18) . . . . ?
C30 C22 C23 C24 -6.1(3) . . . . ?
C17 C18 C23 C22 177.33(19) . . . . ?
C19 C18 C23 C22 -2.2(3) . . . . ?
C17 C18 C23 C24 -1.5(3) . . . . ?
C19 C18 C23 C24 178.89(17) . . . . ?
C22 C23 C24 C29 -74.4(3) . . . . ?
C18 C23 C24 C29 104.4(2) . . . . ?
C22 C23 C24 C25 105.8(2) . . . . ?
C18 C23 C24 C25 -75.3(3) . . . . ?
C29 C24 C25 C26 -0.4(3) . . . . ?
C23 C24 C25 C26 179.4(2) . . . . ?
C24 C25 C26 C27 0.3(4) . . . . ?
C25 C26 C27 C28 0.0(4) . . . . ?
C26 C27 C28 C29 -0.2(4) . . . . ?
C25 C24 C29 C28 0.2(3) . . . . ?
C23 C24 C29 C28 -179.6(2) . . . . ?
C27 C28 C29 C24 0.1(4) . . . . ?
C23 C22 C30 C31 -77.9(3) . . . . ?
C21 C22 C30 C31 100.4(2) . . . . ?
C23 C22 C30 C35 104.6(3) . . . . ?
C21 C22 C30 C35 -77.1(3) . . . . ?
C35 C30 C31 C32 1.6(3) . . . . ?
C22 C30 C31 C32 -176.0(2) . . . . ?
C30 C31 C32 C33 -1.0(4) . . . . ?
C31 C32 C33 C34 -0.6(4) . . . . ?
C32 C33 C34 C35 1.6(4) . . . . ?
C31 C30 C35 C34 -0.6(4) . . . . ?
C22 C30 C35 C34 177.0(2) . . . . ?
C33 C34 C35 C30 -1.0(4) . . . . ?
C20 C21 C36 C37 -73.5(3) . . . . ?
C22 C21 C36 C37 105.9(2) . . . . ?
C20 C21 C36 C41 105.1(2) . . . . ?
C22 C21 C36 C41 -75.4(2) . . . . ?
C41 C36 C37 C38 -1.3(3) . . . . ?
C21 C36 C37 C38 177.4(2) . . . . ?
C36 C37 C38 C39 0.1(4) . . . . ?
C37 C38 C39 C40 1.0(4) . . . . ?
C38 C39 C40 C41 -0.8(4) . . . . ?
C37 C36 C41 C40 1.5(3) . . . . ?
C21 C36 C41 C40 -177.2(2) . . . . ?
C39 C40 C41 C36 -0.4(4) . . . . ?
C21 C20 C42 C47 -78.2(2) . . . . ?
C19 C20 C42 C47 103.0(2) . . . . ?
C21 C20 C42 C43 95.5(2) . . . . ?
C19 C20 C42 C43 -83.3(2) . . . . ?
C47 C42 C43 C44 -1.0(3) . . . . ?
C20 C42 C43 C44 -174.70(18) . . . . ?
C42 C43 C44 C45 0.9(3) . . . . ?
C43 C44 C45 C46 -0.6(4) . . . . ?
C44 C45 C46 C47 0.4(4) . . . . ?
C45 C46 C47 C42 -0.4(4) . . . . ?
C43 C42 C47 C46 0.7(3) . . . . ?
C20 C42 C47 C46 174.6(2) . . . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
N1 H1 Cl1 0.937(16) 2.000(17) 2.9255(18) 169(2) .

_diffrn_measured_fraction_theta_max 0.998
_diffrn_reflns_theta_full        26.00
_diffrn_measured_fraction_theta_full 0.998
_refine_diff_density_max         0.213
_refine_diff_density_min         -0.177
_refine_diff_density_rms         0.038
_database_code_depnum_ccdc_archive 'CCDC 997511'
