# Electronic Supplementary Material (ESI) for Chemical Communications
# This journal is © The Royal Society of Chemistry 2011


data_global
_journal_name_full               Chem.Commun.

_journal_coden_Cambridge         0182
_journal_volume                  ?
_journal_page_first              ?
_journal_year                    ?

_publ_contact_author_name        'Dr Guigen Li'
_publ_contact_author_email       guigen.li@ttu.edu

_publ_section_title              
;
A Multi-component Domino Reaction for the
Direct Access to Polyfunctionalized indoles via
Intermolecular Allylic sp3-C-H Esterification and Indolation
;
loop_
_publ_author_name
'Bo Jiang'
'Mian-Shuai Yi'
'Feng Shi'
'Shujiang Tu'
S.Pindi
P.Mcdowell
'Gguigen Li'

# Attachment '- 4a.cif'

data_100823d
_database_code_depnum_ccdc_archive 'CCDC 846865'
#TrackingRef '- 4a.cif'

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C25 H25 N O3'
_chemical_formula_weight         387.46

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           Monoclinic
_symmetry_space_group_name_H-M   P2(1)

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

_cell_length_a                   8.6760(8)
_cell_length_b                   12.8793(13)
_cell_length_c                   9.4794(11)
_cell_angle_alpha                90.00
_cell_angle_beta                 99.1580(10)
_cell_angle_gamma                90.00
_cell_volume                     1045.73(19)
_cell_formula_units_Z            2
_cell_measurement_temperature    298(2)
_cell_measurement_reflns_used    1086
_cell_measurement_theta_min      2.378
_cell_measurement_theta_max      20.458

_exptl_crystal_description       block
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.40
_exptl_crystal_size_mid          0.21
_exptl_crystal_size_min          0.12
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.231
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             412
_exptl_absorpt_coefficient_mu    0.080
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.9686
_exptl_absorpt_correction_T_max  0.9904
_exptl_absorpt_process_details   sadabs

_exptl_special_details           
;
?
;

_diffrn_ambient_temperature      298(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            5349
_diffrn_reflns_av_R_equivalents  0.0428
_diffrn_reflns_av_sigmaI/netI    0.0559
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_theta_min         2.18
_diffrn_reflns_theta_max         25.02
_reflns_number_total             1936
_reflns_number_gt                1280
_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 F^2^ against ALL reflections. The weighted R-factor wR and
goodness of fit S are based on F^2^, conventional R-factors R are based
on F, with F set to zero for negative F^2^. The threshold expression of
F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is
not relevant to the choice of reflections for refinement. R-factors based
on F^2^ are statistically about twice as large as those based on F, and R-
factors based on ALL data will be even larger.
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[\s^2^(Fo^2^)+(0.0126P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/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   -0.9(15)
_refine_ls_number_reflns         1936
_refine_ls_number_parameters     266
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0638
_refine_ls_R_factor_gt           0.0373
_refine_ls_wR_factor_ref         0.0607
_refine_ls_wR_factor_gt          0.0564
_refine_ls_goodness_of_fit_ref   1.009
_refine_ls_restrained_S_all      1.009
_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 0.4584(3) 0.6454(2) 0.2635(3) 0.0459(7) Uani 1 1 d . . .
O1 O 0.4573(3) 0.99589(18) 0.1814(3) 0.0746(8) Uani 1 1 d . . .
O2 O 0.7184(2) 0.75378(16) 0.5002(2) 0.0574(6) Uani 1 1 d . . .
O3 O 0.9106(3) 0.6387(2) 0.5694(3) 0.0908(9) Uani 1 1 d . . .
C1 C 0.5330(4) 0.9190(3) 0.2262(3) 0.0539(9) Uani 1 1 d . . .
C2 C 0.7034(4) 0.9256(3) 0.2913(4) 0.0590(10) Uani 1 1 d . . .
H2A H 0.7099 0.9456 0.3908 0.071 Uiso 1 1 calc R . .
H2B H 0.7512 0.9807 0.2434 0.071 Uiso 1 1 calc R . .
C3 C 0.8004(4) 0.8255(3) 0.2845(4) 0.0549(9) Uani 1 1 d . . .
C4 C 0.7194(3) 0.7352(3) 0.3484(3) 0.0493(8) Uani 1 1 d . . .
H4 H 0.7717 0.6694 0.3343 0.059 Uiso 1 1 calc R . .
C5 C 0.5517(3) 0.7312(3) 0.2802(3) 0.0419(8) Uani 1 1 d . . .
C6 C 0.4669(4) 0.8155(3) 0.2234(3) 0.0480(9) Uani 1 1 d . . .
C7 C 0.3152(4) 0.7783(3) 0.1692(3) 0.0524(9) Uani 1 1 d . . .
H7 H 0.2323 0.8186 0.1253 0.063 Uiso 1 1 calc R . .
C8 C 0.3107(4) 0.6746(3) 0.1917(3) 0.0491(9) Uani 1 1 d . . .
C9 C 0.1776(4) 0.6028(2) 0.1620(4) 0.0507(9) Uani 1 1 d . . .
C10 C 0.1034(4) 0.5926(3) 0.0211(4) 0.0634(10) Uani 1 1 d . . .
H10 H 0.1433 0.6255 -0.0526 0.076 Uiso 1 1 calc R . .
C11 C -0.0310(5) 0.5326(3) -0.0078(5) 0.0753(12) Uani 1 1 d . . .
H11 H -0.0801 0.5247 -0.1019 0.090 Uiso 1 1 calc R . .
C12 C -0.0914(5) 0.4856(3) 0.0978(6) 0.0807(13) Uani 1 1 d . . .
H12 H -0.1818 0.4460 0.0764 0.097 Uiso 1 1 calc R . .
C13 C -0.0196(5) 0.4960(3) 0.2374(5) 0.0851(13) Uani 1 1 d . . .
H13 H -0.0623 0.4648 0.3108 0.102 Uiso 1 1 calc R . .
C14 C 0.1166(4) 0.5533(3) 0.2677(4) 0.0743(12) Uani 1 1 d . . .
H14 H 0.1672 0.5582 0.3617 0.089 Uiso 1 1 calc R . .
C15 C 0.8137(4) 0.7995(3) 0.1294(3) 0.0668(11) Uani 1 1 d . . .
H15A H 0.8634 0.8560 0.0881 0.100 Uiso 1 1 calc R . .
H15B H 0.7113 0.7886 0.0761 0.100 Uiso 1 1 calc R . .
H15C H 0.8748 0.7376 0.1268 0.100 Uiso 1 1 calc R . .
C16 C 0.9653(4) 0.8444(3) 0.3679(4) 0.0734(12) Uani 1 1 d . . .
H16A H 1.0290 0.7844 0.3602 0.110 Uiso 1 1 calc R . .
H16B H 0.9588 0.8569 0.4667 0.110 Uiso 1 1 calc R . .
H16C H 1.0108 0.9037 0.3290 0.110 Uiso 1 1 calc R . .
C17 C 0.8198(4) 0.7027(3) 0.5987(4) 0.0678(12) Uani 1 1 d . . .
C18 C 0.8013(5) 0.7339(4) 0.7458(4) 0.0949(13) Uani 1 1 d . . .
H18A H 0.7187 0.6943 0.7760 0.142 Uiso 1 1 calc R . .
H18B H 0.7762 0.8065 0.7470 0.142 Uiso 1 1 calc R . .
H18C H 0.8970 0.7213 0.8096 0.142 Uiso 1 1 calc R . .
C19 C 0.5107(3) 0.5396(2) 0.2877(4) 0.0450(9) Uani 1 1 d . . .
C20 C 0.5052(4) 0.4732(3) 0.1749(4) 0.0555(10) Uani 1 1 d . . .
H20 H 0.4666 0.4959 0.0829 0.067 Uiso 1 1 calc R . .
C21 C 0.5576(4) 0.3717(3) 0.1978(4) 0.0616(11) Uani 1 1 d . . .
H21 H 0.5528 0.3264 0.1209 0.074 Uiso 1 1 calc R . .
C22 C 0.6166(4) 0.3375(3) 0.3334(4) 0.0563(10) Uani 1 1 d . . .
C23 C 0.6223(4) 0.4061(3) 0.4450(4) 0.0595(10) Uani 1 1 d . . .
H23 H 0.6636 0.3842 0.5367 0.071 Uiso 1 1 calc R . .
C24 C 0.5687(4) 0.5062(3) 0.4249(3) 0.0535(9) Uani 1 1 d . . .
H24 H 0.5714 0.5510 0.5022 0.064 Uiso 1 1 calc R . .
C25 C 0.6734(4) 0.2259(3) 0.3577(4) 0.0878(13) Uani 1 1 d . . .
H25A H 0.7843 0.2234 0.3601 0.132 Uiso 1 1 calc R . .
H25B H 0.6230 0.1828 0.2814 0.132 Uiso 1 1 calc R . .
H25C H 0.6486 0.2012 0.4470 0.132 Uiso 1 1 calc R . .

loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
N1 0.0413(17) 0.0445(18) 0.0506(18) 0.0041(15) 0.0035(13) 0.0007(15)
O1 0.0824(19) 0.0476(16) 0.090(2) 0.0100(15) 0.0014(15) 0.0102(15)
O2 0.0528(14) 0.0656(17) 0.0518(15) 0.0028(13) 0.0020(11) 0.0069(12)
O3 0.074(2) 0.100(2) 0.094(2) 0.0042(18) -0.0006(16) 0.0299(17)
C1 0.059(3) 0.052(2) 0.053(2) 0.000(2) 0.0147(18) 0.000(2)
C2 0.062(3) 0.049(2) 0.067(3) -0.0023(19) 0.0148(19) -0.0041(19)
C3 0.045(2) 0.055(2) 0.066(3) -0.002(2) 0.0116(18) -0.004(2)
C4 0.046(2) 0.050(2) 0.051(2) -0.0033(19) 0.0056(16) 0.0019(19)
C5 0.0395(19) 0.0436(19) 0.0429(19) -0.0002(18) 0.0076(15) 0.0001(19)
C6 0.050(2) 0.047(2) 0.048(2) 0.0026(17) 0.0101(17) 0.002(2)
C7 0.046(2) 0.055(2) 0.055(2) 0.0081(18) 0.0039(17) 0.0120(18)
C8 0.043(2) 0.050(2) 0.053(2) 0.0042(18) 0.0055(18) 0.0059(19)
C9 0.043(2) 0.047(2) 0.062(3) 0.0053(19) 0.0089(19) 0.0033(18)
C10 0.056(3) 0.065(3) 0.067(3) -0.006(2) 0.005(2) 0.005(2)
C11 0.059(3) 0.073(3) 0.089(3) -0.024(3) -0.004(2) 0.004(2)
C12 0.052(3) 0.069(3) 0.119(4) -0.019(3) 0.008(3) -0.004(2)
C13 0.073(3) 0.078(3) 0.109(4) 0.009(3) 0.027(3) -0.017(3)
C14 0.061(3) 0.078(3) 0.081(3) 0.011(2) 0.004(2) -0.013(2)
C15 0.070(3) 0.067(3) 0.068(3) 0.003(2) 0.026(2) -0.001(2)
C16 0.053(2) 0.074(3) 0.091(3) 0.001(2) 0.005(2) -0.009(2)
C17 0.055(3) 0.071(3) 0.073(3) 0.007(2) -0.002(2) 0.000(2)
C18 0.100(3) 0.131(4) 0.051(3) 0.011(3) 0.004(2) 0.014(3)
C19 0.039(2) 0.040(2) 0.055(2) -0.0001(18) 0.0047(16) 0.0012(16)
C20 0.057(2) 0.053(2) 0.055(2) 0.003(2) 0.0034(18) 0.005(2)
C21 0.062(3) 0.054(2) 0.067(3) -0.012(2) 0.004(2) 0.0001(19)
C22 0.044(2) 0.048(2) 0.077(3) 0.006(2) 0.011(2) -0.0005(19)
C23 0.056(2) 0.057(3) 0.064(3) 0.014(2) 0.0082(18) 0.006(2)
C24 0.056(2) 0.057(2) 0.049(2) 0.0034(18) 0.0111(18) 0.0007(18)
C25 0.078(3) 0.050(2) 0.132(4) 0.007(3) 0.006(2) 0.006(2)

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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
N1 C5 1.364(4) . ?
N1 C8 1.403(3) . ?
N1 C19 1.443(4) . ?
O1 C1 1.226(4) . ?
O2 C17 1.348(4) . ?
O2 C4 1.460(3) . ?
O3 C17 1.203(4) . ?
C1 C6 1.450(4) . ?
C1 C2 1.511(4) . ?
C2 C3 1.547(4) . ?
C2 H2A 0.9700 . ?
C2 H2B 0.9700 . ?
C3 C15 1.530(4) . ?
C3 C4 1.533(4) . ?
C3 C16 1.540(4) . ?
C4 C5 1.496(3) . ?
C4 H4 0.9800 . ?
C5 C6 1.372(4) . ?
C6 C7 1.417(4) . ?
C7 C8 1.355(4) . ?
C7 H7 0.9300 . ?
C8 C9 1.470(4) . ?
C9 C14 1.364(4) . ?
C9 C10 1.394(4) . ?
C10 C11 1.389(4) . ?
C10 H10 0.9300 . ?
C11 C12 1.346(6) . ?
C11 H11 0.9300 . ?
C12 C13 1.377(5) . ?
C12 H12 0.9300 . ?
C13 C14 1.384(5) . ?
C13 H13 0.9300 . ?
C14 H14 0.9300 . ?
C15 H15A 0.9600 . ?
C15 H15B 0.9600 . ?
C15 H15C 0.9600 . ?
C16 H16A 0.9600 . ?
C16 H16B 0.9600 . ?
C16 H16C 0.9600 . ?
C17 C18 1.485(5) . ?
C18 H18A 0.9600 . ?
C18 H18B 0.9600 . ?
C18 H18C 0.9600 . ?
C19 C20 1.364(4) . ?
C19 C24 1.386(4) . ?
C20 C21 1.390(4) . ?
C20 H20 0.9300 . ?
C21 C22 1.378(4) . ?
C21 H21 0.9300 . ?
C22 C23 1.373(4) . ?
C22 C25 1.525(5) . ?
C23 C24 1.374(4) . ?
C23 H23 0.9300 . ?
C24 H24 0.9300 . ?
C25 H25A 0.9600 . ?
C25 H25B 0.9600 . ?
C25 H25C 0.9600 . ?

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
C5 N1 C8 108.6(3) . . ?
C5 N1 C19 125.5(3) . . ?
C8 N1 C19 124.7(3) . . ?
C17 O2 C4 119.8(3) . . ?
O1 C1 C6 123.2(3) . . ?
O1 C1 C2 122.0(3) . . ?
C6 C1 C2 114.7(3) . . ?
C1 C2 C3 116.0(3) . . ?
C1 C2 H2A 108.3 . . ?
C3 C2 H2A 108.3 . . ?
C1 C2 H2B 108.3 . . ?
C3 C2 H2B 108.3 . . ?
H2A C2 H2B 107.4 . . ?
C15 C3 C4 108.8(3) . . ?
C15 C3 C16 108.8(3) . . ?
C4 C3 C16 111.3(3) . . ?
C15 C3 C2 110.3(3) . . ?
C4 C3 C2 109.2(3) . . ?
C16 C3 C2 108.3(3) . . ?
O2 C4 C5 105.9(2) . . ?
O2 C4 C3 109.9(3) . . ?
C5 C4 C3 109.3(3) . . ?
O2 C4 H4 110.6 . . ?
C5 C4 H4 110.6 . . ?
C3 C4 H4 110.6 . . ?
N1 C5 C6 108.9(3) . . ?
N1 C5 C4 126.6(3) . . ?
C6 C5 C4 124.5(3) . . ?
C5 C6 C7 106.5(3) . . ?
C5 C6 C1 122.3(3) . . ?
C7 C6 C1 131.2(3) . . ?
C8 C7 C6 108.9(3) . . ?
C8 C7 H7 125.5 . . ?
C6 C7 H7 125.5 . . ?
C7 C8 N1 107.0(3) . . ?
C7 C8 C9 129.2(3) . . ?
N1 C8 C9 123.6(3) . . ?
C14 C9 C10 119.0(3) . . ?
C14 C9 C8 122.5(3) . . ?
C10 C9 C8 118.2(3) . . ?
C11 C10 C9 119.2(4) . . ?
C11 C10 H10 120.4 . . ?
C9 C10 H10 120.4 . . ?
C12 C11 C10 121.1(4) . . ?
C12 C11 H11 119.4 . . ?
C10 C11 H11 119.4 . . ?
C11 C12 C13 120.1(4) . . ?
C11 C12 H12 120.0 . . ?
C13 C12 H12 120.0 . . ?
C12 C13 C14 119.5(4) . . ?
C12 C13 H13 120.2 . . ?
C14 C13 H13 120.2 . . ?
C9 C14 C13 121.0(4) . . ?
C9 C14 H14 119.5 . . ?
C13 C14 H14 119.5 . . ?
C3 C15 H15A 109.5 . . ?
C3 C15 H15B 109.5 . . ?
H15A C15 H15B 109.5 . . ?
C3 C15 H15C 109.5 . . ?
H15A C15 H15C 109.5 . . ?
H15B C15 H15C 109.5 . . ?
C3 C16 H16A 109.5 . . ?
C3 C16 H16B 109.5 . . ?
H16A C16 H16B 109.5 . . ?
C3 C16 H16C 109.5 . . ?
H16A C16 H16C 109.5 . . ?
H16B C16 H16C 109.5 . . ?
O3 C17 O2 123.6(4) . . ?
O3 C17 C18 125.1(4) . . ?
O2 C17 C18 111.2(4) . . ?
C17 C18 H18A 109.5 . . ?
C17 C18 H18B 109.5 . . ?
H18A C18 H18B 109.5 . . ?
C17 C18 H18C 109.5 . . ?
H18A C18 H18C 109.5 . . ?
H18B C18 H18C 109.5 . . ?
C20 C19 C24 120.3(3) . . ?
C20 C19 N1 119.7(3) . . ?
C24 C19 N1 120.0(3) . . ?
C19 C20 C21 119.8(3) . . ?
C19 C20 H20 120.1 . . ?
C21 C20 H20 120.1 . . ?
C22 C21 C20 120.7(3) . . ?
C22 C21 H21 119.7 . . ?
C20 C21 H21 119.7 . . ?
C23 C22 C21 118.4(3) . . ?
C23 C22 C25 121.3(3) . . ?
C21 C22 C25 120.3(4) . . ?
C22 C23 C24 121.8(3) . . ?
C22 C23 H23 119.1 . . ?
C24 C23 H23 119.1 . . ?
C23 C24 C19 119.0(3) . . ?
C23 C24 H24 120.5 . . ?
C19 C24 H24 120.5 . . ?
C22 C25 H25A 109.5 . . ?
C22 C25 H25B 109.5 . . ?
H25A C25 H25B 109.5 . . ?
C22 C25 H25C 109.5 . . ?
H25A C25 H25C 109.5 . . ?
H25B C25 H25C 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 C1 C2 C3 -155.1(3) . . . . ?
C6 C1 C2 C3 25.8(4) . . . . ?
C1 C2 C3 C15 66.3(4) . . . . ?
C1 C2 C3 C4 -53.3(4) . . . . ?
C1 C2 C3 C16 -174.7(3) . . . . ?
C17 O2 C4 C5 138.9(3) . . . . ?
C17 O2 C4 C3 -103.1(3) . . . . ?
C15 C3 C4 O2 174.7(2) . . . . ?
C16 C3 C4 O2 54.8(3) . . . . ?
C2 C3 C4 O2 -64.8(3) . . . . ?
C15 C3 C4 C5 -69.5(3) . . . . ?
C16 C3 C4 C5 170.6(3) . . . . ?
C2 C3 C4 C5 51.0(3) . . . . ?
C8 N1 C5 C6 1.2(3) . . . . ?
C19 N1 C5 C6 169.2(3) . . . . ?
C8 N1 C5 C4 -178.7(3) . . . . ?
C19 N1 C5 C4 -10.7(5) . . . . ?
O2 C4 C5 N1 -89.1(4) . . . . ?
C3 C4 C5 N1 152.6(3) . . . . ?
O2 C4 C5 C6 91.1(3) . . . . ?
C3 C4 C5 C6 -27.2(4) . . . . ?
N1 C5 C6 C7 -0.3(3) . . . . ?
C4 C5 C6 C7 179.5(3) . . . . ?
N1 C5 C6 C1 179.2(3) . . . . ?
C4 C5 C6 C1 -1.0(5) . . . . ?
O1 C1 C6 C5 -176.8(3) . . . . ?
C2 C1 C6 C5 2.3(4) . . . . ?
O1 C1 C6 C7 2.4(6) . . . . ?
C2 C1 C6 C7 -178.5(3) . . . . ?
C5 C6 C7 C8 -0.7(4) . . . . ?
C1 C6 C7 C8 179.9(3) . . . . ?
C6 C7 C8 N1 1.4(4) . . . . ?
C6 C7 C8 C9 176.1(3) . . . . ?
C5 N1 C8 C7 -1.6(4) . . . . ?
C19 N1 C8 C7 -169.7(3) . . . . ?
C5 N1 C8 C9 -176.6(3) . . . . ?
C19 N1 C8 C9 15.2(5) . . . . ?
C7 C8 C9 C14 -113.6(4) . . . . ?
N1 C8 C9 C14 60.3(5) . . . . ?
C7 C8 C9 C10 60.7(5) . . . . ?
N1 C8 C9 C10 -125.4(3) . . . . ?
C14 C9 C10 C11 0.2(5) . . . . ?
C8 C9 C10 C11 -174.2(3) . . . . ?
C9 C10 C11 C12 0.9(5) . . . . ?
C10 C11 C12 C13 -0.3(6) . . . . ?
C11 C12 C13 C14 -1.3(6) . . . . ?
C10 C9 C14 C13 -1.8(5) . . . . ?
C8 C9 C14 C13 172.3(3) . . . . ?
C12 C13 C14 C9 2.4(6) . . . . ?
C4 O2 C17 O3 -2.4(5) . . . . ?
C4 O2 C17 C18 179.1(3) . . . . ?
C5 N1 C19 C20 -111.3(3) . . . . ?
C8 N1 C19 C20 54.9(4) . . . . ?
C5 N1 C19 C24 67.6(4) . . . . ?
C8 N1 C19 C24 -126.2(3) . . . . ?
C24 C19 C20 C21 0.2(5) . . . . ?
N1 C19 C20 C21 179.1(3) . . . . ?
C19 C20 C21 C22 -0.6(5) . . . . ?
C20 C21 C22 C23 0.0(5) . . . . ?
C20 C21 C22 C25 179.8(3) . . . . ?
C21 C22 C23 C24 1.1(5) . . . . ?
C25 C22 C23 C24 -178.7(3) . . . . ?
C22 C23 C24 C19 -1.6(5) . . . . ?
C20 C19 C24 C23 0.8(5) . . . . ?
N1 C19 C24 C23 -178.1(3) . . . . ?

_diffrn_measured_fraction_theta_max 0.999
_diffrn_reflns_theta_full        25.02
_diffrn_measured_fraction_theta_full 0.999
_refine_diff_density_max         0.098
_refine_diff_density_min         -0.111
_refine_diff_density_rms         0.025

# Attachment '- 5a.cif'

data_101109a
_database_code_depnum_ccdc_archive 'CCDC 846866'
#TrackingRef '- 5a.cif'

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C42 H34 N2 O2'
_chemical_formula_weight         598.71

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           Triclinic
_symmetry_space_group_name_H-M   P-1

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

_cell_length_a                   10.0878(13)
_cell_length_b                   11.1881(13)
_cell_length_c                   15.2089(16)
_cell_angle_alpha                106.600(2)
_cell_angle_beta                 100.541(2)
_cell_angle_gamma                95.9650(10)
_cell_volume                     1594.8(3)
_cell_formula_units_Z            2
_cell_measurement_temperature    298(2)
_cell_measurement_reflns_used    1423
_cell_measurement_theta_min      2.57
_cell_measurement_theta_max      28.085

_exptl_crystal_description       block
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.15
_exptl_crystal_size_mid          0.11
_exptl_crystal_size_min          0.07
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.247
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             632
_exptl_absorpt_coefficient_mu    0.076
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.9886
_exptl_absorpt_correction_T_max  0.9947
_exptl_absorpt_process_details   sadabs

_exptl_special_details           
;
?
;

_diffrn_ambient_temperature      298(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            8283
_diffrn_reflns_av_R_equivalents  0.1165
_diffrn_reflns_av_sigmaI/netI    0.1939
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_theta_min         2.59
_diffrn_reflns_theta_max         25.02
_reflns_number_total             5520
_reflns_number_gt                2007
_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 F^2^ against ALL reflections. The weighted R-factor wR and
goodness of fit S are based on F^2^, conventional R-factors R are based
on F, with F set to zero for negative F^2^. The threshold expression of
F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is
not relevant to the choice of reflections for refinement. R-factors based
on F^2^ are statistically about twice as large as those based on F, and R-
factors based on ALL data will be even larger.
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[\s^2^(Fo^2^)+(0.0530P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         5520
_refine_ls_number_parameters     417
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.2184
_refine_ls_R_factor_gt           0.1000
_refine_ls_wR_factor_ref         0.2288
_refine_ls_wR_factor_gt          0.1950
_refine_ls_goodness_of_fit_ref   1.044
_refine_ls_restrained_S_all      1.044
_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 0.3499(5) 1.2756(4) 0.8534(3) 0.0521(13) Uani 1 1 d . . .
N2 N 0.1915(5) 1.4132(5) 0.5767(3) 0.0533(13) Uani 1 1 d . . .
O1 O 0.4930(4) 1.3490(4) 0.6000(3) 0.0690(13) Uani 1 1 d . . .
H1 H 0.5275 1.3177 0.5558 0.103 Uiso 1 1 calc R . .
O2 O 0.4954(5) 1.7491(4) 0.5791(3) 0.0755(14) Uani 1 1 d . . .
C1 C 0.4774(6) 1.2669(6) 0.6481(4) 0.0517(16) Uani 1 1 d . . .
C2 C 0.5134(6) 1.1469(6) 0.6222(4) 0.0604(17) Uani 1 1 d . . .
H2 H 0.5503 1.1213 0.5694 0.072 Uiso 1 1 calc R . .
C3 C 0.4952(6) 1.0651(6) 0.6740(4) 0.0643(18) Uani 1 1 d . . .
H3 H 0.5181 0.9848 0.6547 0.077 Uiso 1 1 calc R . .
C4 C 0.4432(6) 1.1012(6) 0.7543(4) 0.0572(17) Uani 1 1 d . . .
H4 H 0.4315 1.0469 0.7895 0.069 Uiso 1 1 calc R . .
C5 C 0.4095(6) 1.2206(5) 0.7797(4) 0.0483(15) Uani 1 1 d . . .
C6 C 0.4197(6) 1.3040(5) 0.7271(4) 0.0485(15) Uani 1 1 d . . .
C7 C 0.3586(6) 1.4106(6) 0.7682(4) 0.0517(15) Uani 1 1 d . . .
C8 C 0.3208(6) 1.3912(6) 0.8457(4) 0.0536(16) Uani 1 1 d . . .
C9 C 0.2627(6) 1.4778(5) 0.9193(4) 0.0521(16) Uani 1 1 d . . .
C10 C 0.3243(6) 1.5053(6) 1.0147(4) 0.0581(17) Uani 1 1 d . . .
H10 H 0.3995 1.4686 1.0316 0.070 Uiso 1 1 calc R . .
C11 C 0.2761(7) 1.5848(6) 1.0833(4) 0.0673(19) Uani 1 1 d . . .
H11 H 0.3179 1.6018 1.1463 0.081 Uiso 1 1 calc R . .
C12 C 0.1652(8) 1.6395(6) 1.0583(5) 0.075(2) Uani 1 1 d . . .
H12 H 0.1320 1.6937 1.1049 0.090 Uiso 1 1 calc R . .
C13 C 0.1030(7) 1.6152(6) 0.9658(5) 0.074(2) Uani 1 1 d . . .
H13 H 0.0284 1.6528 0.9493 0.089 Uiso 1 1 calc R . .
C14 C 0.1527(7) 1.5335(6) 0.8966(4) 0.0652(18) Uani 1 1 d . . .
H14 H 0.1103 1.5165 0.8337 0.078 Uiso 1 1 calc R . .
C15 C 0.3204(7) 1.2142(5) 0.9192(4) 0.0504(15) Uani 1 1 d . . .
C16 C 0.4236(6) 1.1778(5) 0.9721(4) 0.0575(17) Uani 1 1 d . . .
H16 H 0.5136 1.1980 0.9681 0.069 Uiso 1 1 calc R . .
C17 C 0.3936(7) 1.1105(6) 1.0317(4) 0.0601(17) Uani 1 1 d . . .
H17 H 0.4647 1.0851 1.0665 0.072 Uiso 1 1 calc R . .
C18 C 0.2640(8) 1.0804(6) 1.0411(4) 0.0612(17) Uani 1 1 d . . .
C19 C 0.1621(7) 1.1227(6) 0.9899(4) 0.0657(18) Uani 1 1 d . . .
H19 H 0.0729 1.1062 0.9966 0.079 Uiso 1 1 calc R . .
C20 C 0.1879(7) 1.1887(6) 0.9287(4) 0.0623(17) Uani 1 1 d . . .
H20 H 0.1172 1.2155 0.8946 0.075 Uiso 1 1 calc R . .
C21 C 0.2327(7) 1.0025(6) 1.1027(5) 0.090(2) Uani 1 1 d . . .
H21A H 0.2078 0.9150 1.0656 0.135 Uiso 1 1 calc R . .
H21B H 0.1582 1.0298 1.1302 0.135 Uiso 1 1 calc R . .
H21C H 0.3119 1.0129 1.1517 0.135 Uiso 1 1 calc R . .
C22 C 0.4496(7) 1.6836(6) 0.6232(4) 0.0560(17) Uani 1 1 d . . .
C23 C 0.5004(7) 1.7201(5) 0.7277(4) 0.0625(18) Uani 1 1 d . . .
H23A H 0.4450 1.7776 0.7583 0.075 Uiso 1 1 calc R . .
H23B H 0.5938 1.7643 0.7448 0.075 Uiso 1 1 calc R . .
C24 C 0.4955(7) 1.6058(5) 0.7636(4) 0.0614(18) Uani 1 1 d . . .
H24A H 0.5584 1.5529 0.7380 0.074 Uiso 1 1 calc R . .
H24B H 0.5268 1.6351 0.8316 0.074 Uiso 1 1 calc R . .
C25 C 0.3546(6) 1.5263(5) 0.7380(4) 0.0532(16) Uani 1 1 d . . .
H25 H 0.2978 1.5776 0.7741 0.064 Uiso 1 1 calc R . .
C26 C 0.2937(6) 1.5060(6) 0.6343(4) 0.0511(16) Uani 1 1 d . . .
C27 C 0.3460(6) 1.5758(6) 0.5823(4) 0.0511(16) Uani 1 1 d . . .
C28 C 0.2687(7) 1.5174(6) 0.4874(4) 0.0614(18) Uani 1 1 d . . .
H28 H 0.2811 1.5432 0.4361 0.074 Uiso 1 1 calc R . .
C29 C 0.1764(7) 1.4207(6) 0.4839(4) 0.0547(17) Uani 1 1 d . . .
C30 C 0.0786(8) 1.3355(6) 0.4010(4) 0.0624(18) Uani 1 1 d . . .
C31 C -0.0495(8) 1.2788(6) 0.4020(4) 0.073(2) Uani 1 1 d . . .
H31 H -0.0774 1.2941 0.4586 0.087 Uiso 1 1 calc R . .
C32 C -0.1371(8) 1.1994(7) 0.3197(5) 0.093(2) Uani 1 1 d . . .
H32 H -0.2206 1.1580 0.3220 0.112 Uiso 1 1 calc R . .
C33 C -0.0999(10) 1.1821(8) 0.2347(6) 0.098(3) Uani 1 1 d . . .
H33 H -0.1594 1.1317 0.1791 0.118 Uiso 1 1 calc R . .
C34 C 0.0244(10) 1.2396(8) 0.2331(5) 0.090(2) Uani 1 1 d . . .
H34 H 0.0491 1.2278 0.1756 0.108 Uiso 1 1 calc R . .
C35 C 0.1153(7) 1.3150(6) 0.3141(5) 0.075(2) Uani 1 1 d . . .
H35 H 0.2005 1.3521 0.3110 0.090 Uiso 1 1 calc R . .
C36 C 0.1124(6) 1.3227(6) 0.6042(4) 0.0522(16) Uani 1 1 d . . .
C37 C 0.1346(6) 1.1998(6) 0.5830(4) 0.0602(17) Uani 1 1 d . . .
H37 H 0.2016 1.1751 0.5503 0.072 Uiso 1 1 calc R . .
C38 C 0.0581(7) 1.1126(6) 0.6100(5) 0.0686(19) Uani 1 1 d . . .
H38 H 0.0760 1.0303 0.5971 0.082 Uiso 1 1 calc R . .
C39 C -0.0454(7) 1.1466(7) 0.6562(5) 0.0661(19) Uani 1 1 d . . .
C40 C -0.0663(7) 1.2702(7) 0.6751(4) 0.0688(19) Uani 1 1 d . . .
H40 H -0.1345 1.2952 0.7066 0.083 Uiso 1 1 calc R . .
C41 C 0.0092(7) 1.3571(6) 0.6495(4) 0.0610(17) Uani 1 1 d . . .
H41 H -0.0087 1.4395 0.6625 0.073 Uiso 1 1 calc R . .
C42 C -0.1304(8) 1.0490(7) 0.6835(5) 0.101(3) Uani 1 1 d . . .
H42A H -0.0714 1.0126 0.7219 0.151 Uiso 1 1 calc R . .
H42B H -0.1807 0.9838 0.6277 0.151 Uiso 1 1 calc R . .
H42C H -0.1931 1.0888 0.7181 0.151 Uiso 1 1 calc R . .

loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
N1 0.071(4) 0.061(3) 0.032(3) 0.028(3) 0.012(3) 0.010(3)
N2 0.074(4) 0.055(3) 0.033(3) 0.022(3) 0.007(3) 0.006(3)
O1 0.106(4) 0.072(3) 0.048(3) 0.033(2) 0.036(2) 0.024(3)
O2 0.122(4) 0.063(3) 0.048(3) 0.027(2) 0.030(3) -0.001(3)
C1 0.063(4) 0.060(4) 0.038(4) 0.023(3) 0.014(3) 0.008(3)
C2 0.073(5) 0.070(5) 0.041(4) 0.018(4) 0.019(3) 0.012(4)
C3 0.075(5) 0.068(4) 0.054(4) 0.020(4) 0.017(4) 0.020(4)
C4 0.082(5) 0.056(4) 0.042(4) 0.025(3) 0.020(3) 0.011(4)
C5 0.063(4) 0.053(4) 0.037(4) 0.026(3) 0.011(3) 0.011(3)
C6 0.059(4) 0.058(4) 0.032(3) 0.018(3) 0.012(3) 0.011(3)
C7 0.061(4) 0.065(4) 0.031(3) 0.018(3) 0.010(3) 0.010(3)
C8 0.068(4) 0.069(4) 0.030(4) 0.028(3) 0.007(3) 0.010(3)
C9 0.067(4) 0.064(4) 0.031(4) 0.024(3) 0.009(3) 0.013(3)
C10 0.073(5) 0.076(5) 0.031(4) 0.025(3) 0.011(3) 0.014(4)
C11 0.076(5) 0.086(5) 0.036(4) 0.016(4) 0.010(4) 0.010(4)
C12 0.094(6) 0.089(5) 0.044(4) 0.018(4) 0.024(4) 0.019(4)
C13 0.091(5) 0.086(5) 0.053(5) 0.024(4) 0.017(4) 0.036(4)
C14 0.084(5) 0.076(5) 0.038(4) 0.024(4) 0.006(3) 0.024(4)
C15 0.067(4) 0.060(4) 0.034(4) 0.025(3) 0.011(3) 0.020(3)
C16 0.070(4) 0.070(4) 0.040(4) 0.028(4) 0.012(3) 0.018(4)
C17 0.078(5) 0.073(5) 0.037(4) 0.030(4) 0.006(3) 0.024(4)
C18 0.082(5) 0.068(4) 0.039(4) 0.026(4) 0.011(4) 0.013(4)
C19 0.074(5) 0.075(5) 0.050(4) 0.030(4) 0.011(4) -0.002(4)
C20 0.071(5) 0.079(5) 0.043(4) 0.032(4) 0.003(3) 0.018(4)
C21 0.123(6) 0.099(6) 0.065(5) 0.053(5) 0.024(4) 0.005(5)
C22 0.086(5) 0.044(4) 0.042(4) 0.021(3) 0.012(4) 0.011(4)
C23 0.087(5) 0.054(4) 0.041(4) 0.018(3) 0.007(3) -0.005(3)
C24 0.084(5) 0.066(4) 0.033(4) 0.021(3) 0.003(3) 0.007(4)
C25 0.075(5) 0.059(4) 0.031(3) 0.023(3) 0.009(3) 0.010(4)
C26 0.071(5) 0.054(4) 0.032(4) 0.022(3) 0.008(3) 0.009(3)
C27 0.073(4) 0.051(4) 0.036(4) 0.025(3) 0.013(3) 0.010(3)
C28 0.086(5) 0.069(5) 0.033(4) 0.025(4) 0.008(3) 0.016(4)
C29 0.079(5) 0.057(4) 0.032(4) 0.020(3) 0.010(3) 0.014(4)
C30 0.083(5) 0.068(5) 0.035(4) 0.017(4) 0.007(4) 0.016(4)
C31 0.081(5) 0.083(5) 0.044(5) 0.010(4) 0.002(4) 0.021(4)
C32 0.090(6) 0.102(6) 0.061(6) 0.001(5) -0.007(5) 0.014(5)
C33 0.105(7) 0.112(7) 0.048(5) -0.002(5) -0.018(5) 0.029(6)
C34 0.115(7) 0.101(7) 0.044(5) 0.014(5) 0.000(5) 0.031(6)
C35 0.093(5) 0.086(5) 0.042(4) 0.015(4) 0.011(4) 0.018(4)
C36 0.069(5) 0.055(4) 0.037(4) 0.027(3) 0.006(3) 0.004(4)
C37 0.074(5) 0.062(5) 0.044(4) 0.020(4) 0.009(3) 0.006(4)
C38 0.083(5) 0.061(4) 0.060(5) 0.028(4) 0.002(4) 0.002(4)
C39 0.078(5) 0.067(5) 0.054(5) 0.033(4) 0.003(4) -0.006(4)
C40 0.079(5) 0.080(5) 0.055(4) 0.034(4) 0.018(4) 0.002(4)
C41 0.076(5) 0.065(4) 0.043(4) 0.022(4) 0.008(4) 0.012(4)
C42 0.110(7) 0.105(6) 0.095(6) 0.048(5) 0.028(5) -0.002(5)

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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
N1 C8 1.388(6) . ?
N1 C5 1.389(6) . ?
N1 C15 1.421(6) . ?
N2 C26 1.355(7) . ?
N2 C29 1.420(6) . ?
N2 C36 1.426(7) . ?
O1 C1 1.341(6) . ?
O1 H1 0.8200 . ?
O2 C22 1.235(6) . ?
C1 C2 1.394(7) . ?
C1 C6 1.406(7) . ?
C2 C3 1.387(7) . ?
C2 H2 0.9300 . ?
C3 C4 1.387(7) . ?
C3 H3 0.9300 . ?
C4 C5 1.377(7) . ?
C4 H4 0.9300 . ?
C5 C6 1.398(7) . ?
C6 C7 1.435(7) . ?
C7 C8 1.370(7) . ?
C7 C25 1.495(7) . ?
C8 C9 1.508(7) . ?
C9 C14 1.366(7) . ?
C9 C10 1.400(7) . ?
C10 C11 1.364(8) . ?
C10 H10 0.9300 . ?
C11 C12 1.375(8) . ?
C11 H11 0.9300 . ?
C12 C13 1.368(8) . ?
C12 H12 0.9300 . ?
C13 C14 1.390(8) . ?
C13 H13 0.9300 . ?
C14 H14 0.9300 . ?
C15 C16 1.366(7) . ?
C15 C20 1.379(8) . ?
C16 C17 1.387(7) . ?
C16 H16 0.9300 . ?
C17 C18 1.359(8) . ?
C17 H17 0.9300 . ?
C18 C19 1.381(8) . ?
C18 C21 1.502(8) . ?
C19 C20 1.386(7) . ?
C19 H19 0.9300 . ?
C20 H20 0.9300 . ?
C21 H21A 0.9600 . ?
C21 H21B 0.9600 . ?
C21 H21C 0.9600 . ?
C22 C27 1.416(8) . ?
C22 C23 1.498(8) . ?
C23 C24 1.526(7) . ?
C23 H23A 0.9700 . ?
C23 H23B 0.9700 . ?
C24 C25 1.517(8) . ?
C24 H24A 0.9700 . ?
C24 H24B 0.9700 . ?
C25 C26 1.526(7) . ?
C25 H25 0.9800 . ?
C26 C27 1.391(7) . ?
C27 C28 1.435(8) . ?
C28 C29 1.334(7) . ?
C28 H28 0.9300 . ?
C29 C30 1.461(8) . ?
C30 C31 1.383(8) . ?
C30 C35 1.400(8) . ?
C31 C32 1.391(9) . ?
C31 H31 0.9300 . ?
C32 C33 1.377(10) . ?
C32 H32 0.9300 . ?
C33 C34 1.357(10) . ?
C33 H33 0.9300 . ?
C34 C35 1.380(9) . ?
C34 H34 0.9300 . ?
C35 H35 0.9300 . ?
C36 C37 1.372(7) . ?
C36 C41 1.378(8) . ?
C37 C38 1.380(8) . ?
C37 H37 0.9300 . ?
C38 C39 1.387(9) . ?
C38 H38 0.9300 . ?
C39 C40 1.377(8) . ?
C39 C42 1.514(8) . ?
C40 C41 1.359(7) . ?
C40 H40 0.9300 . ?
C41 H41 0.9300 . ?
C42 H42A 0.9600 . ?
C42 H42B 0.9600 . ?
C42 H42C 0.9600 . ?

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
C8 N1 C5 107.9(4) . . ?
C8 N1 C15 129.1(5) . . ?
C5 N1 C15 122.9(5) . . ?
C26 N2 C29 108.5(5) . . ?
C26 N2 C36 126.0(5) . . ?
C29 N2 C36 125.5(5) . . ?
C1 O1 H1 109.5 . . ?
O1 C1 C2 123.0(5) . . ?
O1 C1 C6 117.9(5) . . ?
C2 C1 C6 119.1(5) . . ?
C3 C2 C1 120.9(6) . . ?
C3 C2 H2 119.5 . . ?
C1 C2 H2 119.5 . . ?
C4 C3 C2 121.0(6) . . ?
C4 C3 H3 119.5 . . ?
C2 C3 H3 119.5 . . ?
C5 C4 C3 117.4(5) . . ?
C5 C4 H4 121.3 . . ?
C3 C4 H4 121.3 . . ?
C4 C5 N1 128.1(5) . . ?
C4 C5 C6 123.6(5) . . ?
N1 C5 C6 108.0(5) . . ?
C5 C6 C1 117.7(5) . . ?
C5 C6 C7 107.4(5) . . ?
C1 C6 C7 134.8(5) . . ?
C8 C7 C6 106.6(5) . . ?
C8 C7 C25 127.4(5) . . ?
C6 C7 C25 125.6(5) . . ?
C7 C8 N1 110.0(5) . . ?
C7 C8 C9 129.2(5) . . ?
N1 C8 C9 120.7(5) . . ?
C14 C9 C10 118.0(6) . . ?
C14 C9 C8 122.4(5) . . ?
C10 C9 C8 119.6(5) . . ?
C11 C10 C9 121.4(6) . . ?
C11 C10 H10 119.3 . . ?
C9 C10 H10 119.3 . . ?
C10 C11 C12 119.4(6) . . ?
C10 C11 H11 120.3 . . ?
C12 C11 H11 120.3 . . ?
C13 C12 C11 120.8(7) . . ?
C13 C12 H12 119.6 . . ?
C11 C12 H12 119.6 . . ?
C12 C13 C14 119.3(7) . . ?
C12 C13 H13 120.4 . . ?
C14 C13 H13 120.4 . . ?
C9 C14 C13 121.2(6) . . ?
C9 C14 H14 119.4 . . ?
C13 C14 H14 119.4 . . ?
C16 C15 C20 119.7(5) . . ?
C16 C15 N1 119.8(6) . . ?
C20 C15 N1 120.5(5) . . ?
C15 C16 C17 119.8(6) . . ?
C15 C16 H16 120.1 . . ?
C17 C16 H16 120.1 . . ?
C18 C17 C16 122.3(6) . . ?
C18 C17 H17 118.8 . . ?
C16 C17 H17 118.8 . . ?
C17 C18 C19 116.9(6) . . ?
C17 C18 C21 121.6(6) . . ?
C19 C18 C21 121.5(6) . . ?
C18 C19 C20 122.4(6) . . ?
C18 C19 H19 118.8 . . ?
C20 C19 H19 118.8 . . ?
C15 C20 C19 118.9(6) . . ?
C15 C20 H20 120.6 . . ?
C19 C20 H20 120.6 . . ?
C18 C21 H21A 109.5 . . ?
C18 C21 H21B 109.5 . . ?
H21A C21 H21B 109.5 . . ?
C18 C21 H21C 109.5 . . ?
H21A C21 H21C 109.5 . . ?
H21B C21 H21C 109.5 . . ?
O2 C22 C27 124.4(6) . . ?
O2 C22 C23 119.7(6) . . ?
C27 C22 C23 115.9(5) . . ?
C22 C23 C24 112.4(5) . . ?
C22 C23 H23A 109.1 . . ?
C24 C23 H23A 109.1 . . ?
C22 C23 H23B 109.1 . . ?
C24 C23 H23B 109.1 . . ?
H23A C23 H23B 107.9 . . ?
C25 C24 C23 113.8(5) . . ?
C25 C24 H24A 108.8 . . ?
C23 C24 H24A 108.8 . . ?
C25 C24 H24B 108.8 . . ?
C23 C24 H24B 108.8 . . ?
H24A C24 H24B 107.7 . . ?
C7 C25 C24 111.2(5) . . ?
C7 C25 C26 116.8(5) . . ?
C24 C25 C26 108.1(5) . . ?
C7 C25 H25 106.7 . . ?
C24 C25 H25 106.7 . . ?
C26 C25 H25 106.7 . . ?
N2 C26 C27 109.4(5) . . ?
N2 C26 C25 126.9(5) . . ?
C27 C26 C25 123.5(6) . . ?
C26 C27 C22 123.1(6) . . ?
C26 C27 C28 105.1(6) . . ?
C22 C27 C28 131.8(5) . . ?
C29 C28 C27 109.9(5) . . ?
C29 C28 H28 125.1 . . ?
C27 C28 H28 125.1 . . ?
C28 C29 N2 107.2(5) . . ?
C28 C29 C30 127.5(6) . . ?
N2 C29 C30 125.3(6) . . ?
C31 C30 C35 118.1(6) . . ?
C31 C30 C29 124.6(6) . . ?
C35 C30 C29 117.2(7) . . ?
C30 C31 C32 121.0(7) . . ?
C30 C31 H31 119.5 . . ?
C32 C31 H31 119.5 . . ?
C33 C32 C31 119.9(8) . . ?
C33 C32 H32 120.1 . . ?
C31 C32 H32 120.1 . . ?
C34 C33 C32 119.2(8) . . ?
C34 C33 H33 120.4 . . ?
C32 C33 H33 120.4 . . ?
C33 C34 C35 122.0(8) . . ?
C33 C34 H34 119.0 . . ?
C35 C34 H34 119.0 . . ?
C34 C35 C30 119.7(7) . . ?
C34 C35 H35 120.2 . . ?
C30 C35 H35 120.2 . . ?
C37 C36 C41 119.3(6) . . ?
C37 C36 N2 120.6(6) . . ?
C41 C36 N2 120.0(6) . . ?
C36 C37 C38 120.3(6) . . ?
C36 C37 H37 119.8 . . ?
C38 C37 H37 119.8 . . ?
C37 C38 C39 120.7(6) . . ?
C37 C38 H38 119.6 . . ?
C39 C38 H38 119.6 . . ?
C40 C39 C38 117.4(6) . . ?
C40 C39 C42 122.6(7) . . ?
C38 C39 C42 120.0(7) . . ?
C41 C40 C39 122.4(7) . . ?
C41 C40 H40 118.8 . . ?
C39 C40 H40 118.8 . . ?
C40 C41 C36 119.8(6) . . ?
C40 C41 H41 120.1 . . ?
C36 C41 H41 120.1 . . ?
C39 C42 H42A 109.5 . . ?
C39 C42 H42B 109.5 . . ?
H42A C42 H42B 109.5 . . ?
C39 C42 H42C 109.5 . . ?
H42A C42 H42C 109.5 . . ?
H42B C42 H42C 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 C1 C2 C3 -179.9(6) . . . . ?
C6 C1 C2 C3 -1.1(9) . . . . ?
C1 C2 C3 C4 -1.3(10) . . . . ?
C2 C3 C4 C5 0.6(9) . . . . ?
C3 C4 C5 N1 176.4(6) . . . . ?
C3 C4 C5 C6 2.7(9) . . . . ?
C8 N1 C5 C4 -173.4(6) . . . . ?
C15 N1 C5 C4 3.5(9) . . . . ?
C8 N1 C5 C6 1.1(6) . . . . ?
C15 N1 C5 C6 178.0(5) . . . . ?
C4 C5 C6 C1 -5.1(9) . . . . ?
N1 C5 C6 C1 -179.9(5) . . . . ?
C4 C5 C6 C7 172.3(6) . . . . ?
N1 C5 C6 C7 -2.5(6) . . . . ?
O1 C1 C6 C5 -177.0(5) . . . . ?
C2 C1 C6 C5 4.1(8) . . . . ?
O1 C1 C6 C7 6.5(10) . . . . ?
C2 C1 C6 C7 -172.3(6) . . . . ?
C5 C6 C7 C8 3.0(7) . . . . ?
C1 C6 C7 C8 179.7(6) . . . . ?
C5 C6 C7 C25 176.1(6) . . . . ?
C1 C6 C7 C25 -7.2(11) . . . . ?
C6 C7 C8 N1 -2.4(7) . . . . ?
C25 C7 C8 N1 -175.3(5) . . . . ?
C6 C7 C8 C9 174.5(6) . . . . ?
C25 C7 C8 C9 1.6(10) . . . . ?
C5 N1 C8 C7 0.8(7) . . . . ?
C15 N1 C8 C7 -175.8(6) . . . . ?
C5 N1 C8 C9 -176.4(5) . . . . ?
C15 N1 C8 C9 7.1(9) . . . . ?
C7 C8 C9 C14 51.0(9) . . . . ?
N1 C8 C9 C14 -132.4(6) . . . . ?
C7 C8 C9 C10 -127.6(7) . . . . ?
N1 C8 C9 C10 49.0(8) . . . . ?
C14 C9 C10 C11 0.3(9) . . . . ?
C8 C9 C10 C11 178.9(5) . . . . ?
C9 C10 C11 C12 -0.2(10) . . . . ?
C10 C11 C12 C13 -0.1(10) . . . . ?
C11 C12 C13 C14 0.4(10) . . . . ?
C10 C9 C14 C13 0.0(9) . . . . ?
C8 C9 C14 C13 -178.6(6) . . . . ?
C12 C13 C14 C9 -0.3(10) . . . . ?
C8 N1 C15 C16 -124.9(6) . . . . ?
C5 N1 C15 C16 59.0(8) . . . . ?
C8 N1 C15 C20 56.5(9) . . . . ?
C5 N1 C15 C20 -119.7(6) . . . . ?
C20 C15 C16 C17 2.9(9) . . . . ?
N1 C15 C16 C17 -175.7(5) . . . . ?
C15 C16 C17 C18 -1.0(9) . . . . ?
C16 C17 C18 C19 -1.6(10) . . . . ?
C16 C17 C18 C21 177.2(6) . . . . ?
C17 C18 C19 C20 2.4(10) . . . . ?
C21 C18 C19 C20 -176.4(6) . . . . ?
C16 C15 C20 C19 -2.1(9) . . . . ?
N1 C15 C20 C19 176.5(5) . . . . ?
C18 C19 C20 C15 -0.6(9) . . . . ?
O2 C22 C23 C24 -150.4(5) . . . . ?
C27 C22 C23 C24 31.9(8) . . . . ?
C22 C23 C24 C25 -56.8(7) . . . . ?
C8 C7 C25 C24 101.5(7) . . . . ?
C6 C7 C25 C24 -70.1(7) . . . . ?
C8 C7 C25 C26 -133.8(6) . . . . ?
C6 C7 C25 C26 54.6(8) . . . . ?
C23 C24 C25 C7 175.4(5) . . . . ?
C23 C24 C25 C26 46.0(6) . . . . ?
C29 N2 C26 C27 0.6(6) . . . . ?
C36 N2 C26 C27 -179.6(5) . . . . ?
C29 N2 C26 C25 -173.8(5) . . . . ?
C36 N2 C26 C25 5.9(9) . . . . ?
C7 C25 C26 N2 32.7(9) . . . . ?
C24 C25 C26 N2 159.0(6) . . . . ?
C7 C25 C26 C27 -141.0(6) . . . . ?
C24 C25 C26 C27 -14.7(8) . . . . ?
N2 C26 C27 C22 176.7(5) . . . . ?
C25 C26 C27 C22 -8.6(9) . . . . ?
N2 C26 C27 C28 -0.7(6) . . . . ?
C25 C26 C27 C28 174.0(5) . . . . ?
O2 C22 C27 C26 -178.1(6) . . . . ?
C23 C22 C27 C26 -0.4(8) . . . . ?
O2 C22 C27 C28 -1.4(10) . . . . ?
C23 C22 C27 C28 176.2(6) . . . . ?
C26 C27 C28 C29 0.5(7) . . . . ?
C22 C27 C28 C29 -176.6(6) . . . . ?
C27 C28 C29 N2 -0.2(7) . . . . ?
C27 C28 C29 C30 -179.2(6) . . . . ?
C26 N2 C29 C28 -0.3(7) . . . . ?
C36 N2 C29 C28 180.0(5) . . . . ?
C26 N2 C29 C30 178.8(6) . . . . ?
C36 N2 C29 C30 -1.0(9) . . . . ?
C28 C29 C30 C31 -148.6(7) . . . . ?
N2 C29 C30 C31 32.6(10) . . . . ?
C28 C29 C30 C35 28.2(10) . . . . ?
N2 C29 C30 C35 -150.6(6) . . . . ?
C35 C30 C31 C32 2.7(10) . . . . ?
C29 C30 C31 C32 179.5(6) . . . . ?
C30 C31 C32 C33 -3.8(11) . . . . ?
C31 C32 C33 C34 2.4(12) . . . . ?
C32 C33 C34 C35 0.0(13) . . . . ?
C33 C34 C35 C30 -1.1(11) . . . . ?
C31 C30 C35 C34 -0.3(10) . . . . ?
C29 C30 C35 C34 -177.3(6) . . . . ?
C26 N2 C36 C37 -105.0(7) . . . . ?
C29 N2 C36 C37 74.7(8) . . . . ?
C26 N2 C36 C41 77.4(8) . . . . ?
C29 N2 C36 C41 -102.9(7) . . . . ?
C41 C36 C37 C38 -2.6(9) . . . . ?
N2 C36 C37 C38 179.8(5) . . . . ?
C36 C37 C38 C39 2.1(9) . . . . ?
C37 C38 C39 C40 -1.1(10) . . . . ?
C37 C38 C39 C42 178.7(6) . . . . ?
C38 C39 C40 C41 0.6(10) . . . . ?
C42 C39 C40 C41 -179.2(6) . . . . ?
C39 C40 C41 C36 -1.1(9) . . . . ?
C37 C36 C41 C40 2.0(9) . . . . ?
N2 C36 C41 C40 179.7(5) . . . . ?

_diffrn_measured_fraction_theta_max 0.982
_diffrn_reflns_theta_full        25.02
_diffrn_measured_fraction_theta_full 0.982
_refine_diff_density_max         0.255
_refine_diff_density_min         -0.295
_refine_diff_density_rms         0.064