# Electronic Supplementary Material (ESI) for Chemical Communications.
# 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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# 
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#  data retrieval see:
#                         www.ccdc.cam.ac.uk
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#  from this site to visualise CIF-encoded structures and 
#  to carry out CIF format checking respectively.
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data_9APDMAD

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
'Dimethyl 8-t-butyl-2a,13b-dihydrobenzo[7,8]indolizino[6,5,4,3-def]phenanthridine-1,2-dicarboxylate'
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C30 H27 N O4'
_chemical_formula_sum            'C30 H27 N O4'
_chemical_formula_weight         465.53

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   P21/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                   16.322(6)
_cell_length_b                   9.073(3)
_cell_length_c                   16.857(6)
_cell_angle_alpha                90.00
_cell_angle_beta                 114.032(4)
_cell_angle_gamma                90.00
_cell_volume                     2280.0(14)
_cell_formula_units_Z            4
_cell_measurement_temperature    93
_cell_measurement_reflns_used    6221
_cell_measurement_theta_min      2.9
_cell_measurement_theta_max      31.7

_exptl_crystal_description       Block
_exptl_crystal_colour            Yellow
_exptl_crystal_size_max          0.30
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.10
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.356
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             984
_exptl_absorpt_coefficient_mu    0.090
_exptl_absorpt_correction_type   Multi-scan
_exptl_absorpt_correction_T_min  0.9736
_exptl_absorpt_correction_T_max  0.9911
_exptl_absorpt_process_details   'Jacobson, R. (1998) Private communication'

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      93(2)
_diffrn_radiation_wavelength     0.71075
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Rigaku Saturn724 CCD'
_diffrn_measurement_method       'omega scans'
_diffrn_detector_area_resol_mean 28.5714
_diffrn_reflns_number            14803
_diffrn_reflns_av_R_equivalents  0.0586
_diffrn_reflns_av_sigmaI/netI    0.0526
_diffrn_reflns_limit_h_min       -19
_diffrn_reflns_limit_h_max       19
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_theta_min         2.93
_diffrn_reflns_theta_max         25.00
_reflns_number_total             4011
_reflns_number_gt                3445
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'RIGAKU CrystalClear'
_computing_cell_refinement       'RIGAKU CrystalClear'
_computing_data_reduction        'RIGAKU CrystalClear'
_computing_structure_solution    SIR-97
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    ORTEP-III
_computing_publication_material  ?

_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)+(0.0346P)²+2.3373P] 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_number_reflns         4011
_refine_ls_number_parameters     321
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0820
_refine_ls_R_factor_gt           0.0676
_refine_ls_wR_factor_ref         0.1310
_refine_ls_wR_factor_gt          0.1240
_refine_ls_goodness_of_fit_ref   1.167
_refine_ls_restrained_S_all      1.167
_refine_ls_shift/su_max          0.003
_refine_ls_shift/su_mean         0.001

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
O3 O 0.19959(12) 0.0534(2) 0.03282(12) 0.0187(4) Uani 1 1 d . . .
O2 O 0.29801(12) -0.0634(2) -0.12754(12) 0.0200(5) Uani 1 1 d . . .
N1 N 0.35158(14) 0.3915(2) -0.01969(13) 0.0139(5) Uani 1 1 d . . .
O4 O 0.31154(12) -0.10036(19) 0.04219(12) 0.0160(4) Uani 1 1 d . . .
C17 C 0.35728(17) 0.4194(3) -0.18428(16) 0.0135(6) Uani 1 1 d . . .
C4 C 0.33567(17) 0.3062(3) 0.04765(16) 0.0120(6) Uani 1 1 d . . .
H2 H 0.3924 0.3081 0.1017 0.014 Uiso 1 1 calc R . .
C5 C 0.26297(17) 0.3695(3) 0.06950(16) 0.0131(6) Uani 1 1 d . . .
O1 O 0.44327(13) -0.0229(2) -0.09976(13) 0.0258(5) Uani 1 1 d . . .
C9 C 0.12194(17) 0.4954(3) 0.02435(17) 0.0155(6) Uani 1 1 d . . .
H6 H 0.0720 0.5428 -0.0193 0.019 Uiso 1 1 calc R . .
C23 C 0.37593(18) 0.0104(3) -0.09148(17) 0.0166(6) Uani 1 1 d . . .
C1 C 0.41067(17) 0.2908(3) -0.04125(16) 0.0129(6) Uani 1 1 d . . .
H1 H 0.4703 0.2905 0.0094 0.015 Uiso 1 1 calc R . .
C3 C 0.32394(16) 0.1485(3) 0.01009(16) 0.0118(5) Uani 1 1 d . . .
C14 C 0.19135(17) 0.4624(3) -0.24842(16) 0.0140(6) Uani 1 1 d . . .
H8 H 0.1926 0.4677 -0.3042 0.017 Uiso 1 1 calc R . .
C11 C 0.18926(17) 0.4431(3) -0.08436(16) 0.0130(6) Uani 1 1 d . . .
C16 C 0.26973(17) 0.4211(3) -0.09349(16) 0.0115(5) Uani 1 1 d . . .
C15 C 0.27122(17) 0.4354(3) -0.17604(16) 0.0127(6) Uani 1 1 d . . .
C10 C 0.18944(17) 0.4350(3) 0.00346(16) 0.0132(6) Uani 1 1 d . . .
C2 C 0.36640(17) 0.1402(3) -0.04262(16) 0.0142(6) Uani 1 1 d . . .
C25 C 0.27140(17) 0.0315(3) 0.02960(16) 0.0132(6) Uani 1 1 d . . .
C28 C 0.03519(19) 0.6512(3) -0.36726(18) 0.0230(7) Uani 1 1 d . . .
H19 H -0.0195 0.6702 -0.4195 0.034 Uiso 1 1 calc R . .
H20 H 0.0862 0.6404 -0.3834 0.034 Uiso 1 1 calc R . .
H21 H 0.0463 0.7338 -0.3267 0.034 Uiso 1 1 calc R . .
C13 C 0.10988(17) 0.4819(3) -0.24133(16) 0.0132(6) Uani 1 1 d . . .
C19 C 0.45454(18) 0.4547(3) -0.25932(18) 0.0189(6) Uani 1 1 d . . .
H10 H 0.4648 0.4953 -0.3064 0.023 Uiso 1 1 calc R . .
C22 C 0.42570(17) 0.3409(3) -0.11919(17) 0.0139(6) Uani 1 1 d . . .
C21 C 0.50673(18) 0.3162(3) -0.12576(18) 0.0194(6) Uani 1 1 d . . .
H12 H 0.5528 0.2621 -0.0818 0.023 Uiso 1 1 calc R . .
C27 C 0.02365(18) 0.5092(3) -0.32379(17) 0.0158(6) Uani 1 1 d . . .
C6 C 0.26877(18) 0.3640(3) 0.15413(17) 0.0150(6) Uani 1 1 d . . .
H3 H 0.3202 0.3222 0.1989 0.018 Uiso 1 1 calc R . .
C8 C 0.12732(18) 0.4864(3) 0.10822(17) 0.0158(6) Uani 1 1 d . . .
H5 H 0.0806 0.5270 0.1214 0.019 Uiso 1 1 calc R . .
C20 C 0.52046(18) 0.3704(3) -0.19656(18) 0.0214(6) Uani 1 1 d . . .
H11 H 0.5750 0.3499 -0.2021 0.026 Uiso 1 1 calc R . .
C12 C 0.11095(17) 0.4731(3) -0.15856(16) 0.0136(6) Uani 1 1 d . . .
H7 H 0.0564 0.4879 -0.1520 0.016 Uiso 1 1 calc R . .
C18 C 0.37389(17) 0.4788(3) -0.25267(17) 0.0145(6) Uani 1 1 d . . .
H9 H 0.3290 0.5368 -0.2954 0.017 Uiso 1 1 calc R . .
C26 C 0.25577(19) -0.2228(3) 0.04340(19) 0.0225(7) Uani 1 1 d . . .
H16 H 0.2383 -0.2116 0.0922 0.034 Uiso 1 1 calc R . .
H17 H 0.2892 -0.3150 0.0500 0.034 Uiso 1 1 calc R . .
H18 H 0.2019 -0.2252 -0.0112 0.034 Uiso 1 1 calc R . .
C7 C 0.19977(18) 0.4192(3) 0.17339(17) 0.0179(6) Uani 1 1 d . . .
H4 H 0.2021 0.4110 0.2305 0.021 Uiso 1 1 calc R . .
C30 C 0.00778(19) 0.3798(3) -0.38699(18) 0.0228(7) Uani 1 1 d . . .
H25 H -0.0027 0.2896 -0.3605 0.034 Uiso 1 1 calc R . .
H26 H 0.0606 0.3667 -0.4000 0.034 Uiso 1 1 calc R . .
H27 H -0.0447 0.4005 -0.4409 0.034 Uiso 1 1 calc R . .
C29 C -0.05896(18) 0.5271(4) -0.30393(18) 0.0234(7) Uani 1 1 d . . .
H22 H -0.0500 0.6102 -0.2641 0.035 Uiso 1 1 calc R . .
H23 H -0.0684 0.4368 -0.2769 0.035 Uiso 1 1 calc R . .
H24 H -0.1116 0.5459 -0.3580 0.035 Uiso 1 1 calc R . .
C24 C 0.3017(2) -0.1997(3) -0.1700(2) 0.0307(8) Uani 1 1 d . . .
H13 H 0.3187 -0.1793 -0.2183 0.046 Uiso 1 1 calc R . .
H14 H 0.2427 -0.2472 -0.1922 0.046 Uiso 1 1 calc R . .
H15 H 0.3462 -0.2653 -0.1283 0.046 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
O3 C25 1.212(3) . ?
O2 C23 1.344(3) . ?
O2 C24 1.442(3) . ?
N1 C16 1.432(3) . ?
N1 C1 1.477(3) . ?
N1 C4 1.481(3) . ?
O4 C25 1.339(3) . ?
O4 C26 1.442(3) . ?
C17 C18 1.396(4) . ?
C17 C22 1.400(4) . ?
C17 C15 1.474(4) . ?
C4 C5 1.493(3) . ?
C4 C3 1.545(4) . ?
C4 H2 1.0000 . ?
C5 C6 1.392(4) . ?
C5 C10 1.395(4) . ?
O1 C23 1.201(3) . ?
C9 C8 1.383(4) . ?
C9 C10 1.398(4) . ?
C9 H6 0.9500 . ?
C23 C2 1.482(4) . ?
C1 C22 1.502(3) . ?
C1 C2 1.541(4) . ?
C1 H1 1.0000 . ?
C3 C2 1.333(4) . ?
C3 C25 1.483(4) . ?
C14 C13 1.394(4) . ?
C14 C15 1.398(4) . ?
C14 H8 0.9500 . ?
C11 C16 1.398(4) . ?
C11 C12 1.404(4) . ?
C11 C10 1.481(4) . ?
C16 C15 1.407(4) . ?
C28 C27 1.531(4) . ?
C28 H19 0.9800 . ?
C28 H20 0.9800 . ?
C28 H21 0.9800 . ?
C13 C12 1.390(4) . ?
C13 C27 1.543(4) . ?
C19 C18 1.383(4) . ?
C19 C20 1.391(4) . ?
C19 H10 0.9500 . ?
C22 C21 1.390(4) . ?
C21 C20 1.391(4) . ?
C21 H12 0.9500 . ?
C27 C29 1.525(4) . ?
C27 C30 1.535(4) . ?
C6 C7 1.387(4) . ?
C6 H3 0.9500 . ?
C8 C7 1.385(4) . ?
C8 H5 0.9500 . ?
C20 H11 0.9500 . ?
C12 H7 0.9500 . ?
C18 H9 0.9500 . ?
C26 H16 0.9800 . ?
C26 H17 0.9800 . ?
C26 H18 0.9800 . ?
C7 H4 0.9500 . ?
C30 H25 0.9800 . ?
C30 H26 0.9800 . ?
C30 H27 0.9800 . ?
C29 H22 0.9800 . ?
C29 H23 0.9800 . ?
C29 H24 0.9800 . ?
C24 H13 0.9800 . ?
C24 H14 0.9800 . ?
C24 H15 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
C23 O2 C24 115.4(2) . . ?
C16 N1 C1 112.0(2) . . ?
C16 N1 C4 111.8(2) . . ?
C1 N1 C4 101.64(19) . . ?
C25 O4 C26 114.8(2) . . ?
C18 C17 C22 118.8(2) . . ?
C18 C17 C15 123.6(2) . . ?
C22 C17 C15 117.6(2) . . ?
N1 C4 C5 113.2(2) . . ?
N1 C4 C3 101.58(19) . . ?
C5 C4 C3 118.6(2) . . ?
N1 C4 H2 107.6 . . ?
C5 C4 H2 107.6 . . ?
C3 C4 H2 107.6 . . ?
C6 C5 C10 120.7(2) . . ?
C6 C5 C4 120.7(2) . . ?
C10 C5 C4 118.6(2) . . ?
C8 C9 C10 120.4(2) . . ?
C8 C9 H6 119.8 . . ?
C10 C9 H6 119.8 . . ?
O1 C23 O2 124.4(3) . . ?
O1 C23 C2 124.9(3) . . ?
O2 C23 C2 110.7(2) . . ?
N1 C1 C22 112.6(2) . . ?
N1 C1 C2 101.7(2) . . ?
C22 C1 C2 119.9(2) . . ?
N1 C1 H1 107.3 . . ?
C22 C1 H1 107.3 . . ?
C2 C1 H1 107.3 . . ?
C2 C3 C25 127.7(2) . . ?
C2 C3 C4 108.3(2) . . ?
C25 C3 C4 124.0(2) . . ?
C13 C14 C15 122.0(2) . . ?
C13 C14 H8 119.0 . . ?
C15 C14 H8 119.0 . . ?
C16 C11 C12 119.0(2) . . ?
C16 C11 C10 118.9(2) . . ?
C12 C11 C10 122.1(2) . . ?
C11 C16 C15 119.4(2) . . ?
C11 C16 N1 121.1(2) . . ?
C15 C16 N1 119.4(2) . . ?
C14 C15 C16 119.6(2) . . ?
C14 C15 C17 121.4(2) . . ?
C16 C15 C17 119.0(2) . . ?
C5 C10 C9 118.4(2) . . ?
C5 C10 C11 118.0(2) . . ?
C9 C10 C11 123.5(2) . . ?
C3 C2 C23 128.0(3) . . ?
C3 C2 C1 107.9(2) . . ?
C23 C2 C1 124.0(2) . . ?
O3 C25 O4 124.0(2) . . ?
O3 C25 C3 123.3(2) . . ?
O4 C25 C3 112.6(2) . . ?
C27 C28 H19 109.5 . . ?
C27 C28 H20 109.5 . . ?
H19 C28 H20 109.5 . . ?
C27 C28 H21 109.5 . . ?
H19 C28 H21 109.5 . . ?
H20 C28 H21 109.5 . . ?
C12 C13 C14 117.1(2) . . ?
C12 C13 C27 123.2(2) . . ?
C14 C13 C27 119.7(2) . . ?
C18 C19 C20 119.5(3) . . ?
C18 C19 H10 120.3 . . ?
C20 C19 H10 120.3 . . ?
C21 C22 C17 120.1(2) . . ?
C21 C22 C1 121.4(2) . . ?
C17 C22 C1 118.5(2) . . ?
C22 C21 C20 120.2(3) . . ?
C22 C21 H12 119.9 . . ?
C20 C21 H12 119.9 . . ?
C29 C27 C28 107.9(2) . . ?
C29 C27 C30 108.6(2) . . ?
C28 C27 C30 109.3(2) . . ?
C29 C27 C13 112.5(2) . . ?
C28 C27 C13 108.7(2) . . ?
C30 C27 C13 109.7(2) . . ?
C7 C6 C5 120.3(2) . . ?
C7 C6 H3 119.9 . . ?
C5 C6 H3 119.9 . . ?
C9 C8 C7 121.0(3) . . ?
C9 C8 H5 119.5 . . ?
C7 C8 H5 119.5 . . ?
C19 C20 C21 120.1(3) . . ?
C19 C20 H11 119.9 . . ?
C21 C20 H11 119.9 . . ?
C13 C12 C11 122.7(2) . . ?
C13 C12 H7 118.6 . . ?
C11 C12 H7 118.6 . . ?
C19 C18 C17 121.1(2) . . ?
C19 C18 H9 119.4 . . ?
C17 C18 H9 119.4 . . ?
O4 C26 H16 109.5 . . ?
O4 C26 H17 109.5 . . ?
H16 C26 H17 109.5 . . ?
O4 C26 H18 109.5 . . ?
H16 C26 H18 109.5 . . ?
H17 C26 H18 109.5 . . ?
C8 C7 C6 119.1(2) . . ?
C8 C7 H4 120.5 . . ?
C6 C7 H4 120.5 . . ?
C27 C30 H25 109.5 . . ?
C27 C30 H26 109.5 . . ?
H25 C30 H26 109.5 . . ?
C27 C30 H27 109.5 . . ?
H25 C30 H27 109.5 . . ?
H26 C30 H27 109.5 . . ?
C27 C29 H22 109.5 . . ?
C27 C29 H23 109.5 . . ?
H22 C29 H23 109.5 . . ?
C27 C29 H24 109.5 . . ?
H22 C29 H24 109.5 . . ?
H23 C29 H24 109.5 . . ?
O2 C24 H13 109.5 . . ?
O2 C24 H14 109.5 . . ?
H13 C24 H14 109.5 . . ?
O2 C24 H15 109.5 . . ?
H13 C24 H15 109.5 . . ?
H14 C24 H15 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
C16 N1 C4 C5 -49.2(3) . . . . ?
C1 N1 C4 C5 -168.8(2) . . . . ?
C16 N1 C4 C3 79.1(2) . . . . ?
C1 N1 C4 C3 -40.5(2) . . . . ?
N1 C4 C5 C6 -144.5(2) . . . . ?
C3 C4 C5 C6 96.7(3) . . . . ?
N1 C4 C5 C10 35.1(3) . . . . ?
C3 C4 C5 C10 -83.7(3) . . . . ?
C24 O2 C23 O1 7.2(4) . . . . ?
C24 O2 C23 C2 -174.5(2) . . . . ?
C16 N1 C1 C22 51.5(3) . . . . ?
C4 N1 C1 C22 170.9(2) . . . . ?
C16 N1 C1 C2 -78.1(2) . . . . ?
C4 N1 C1 C2 41.4(2) . . . . ?
N1 C4 C3 C2 24.6(3) . . . . ?
C5 C4 C3 C2 149.3(2) . . . . ?
N1 C4 C3 C25 -153.8(2) . . . . ?
C5 C4 C3 C25 -29.1(3) . . . . ?
C12 C11 C16 C15 2.6(4) . . . . ?
C10 C11 C16 C15 -177.0(2) . . . . ?
C12 C11 C16 N1 179.5(2) . . . . ?
C10 C11 C16 N1 -0.2(4) . . . . ?
C1 N1 C16 C11 146.1(2) . . . . ?
C4 N1 C16 C11 32.9(3) . . . . ?
C1 N1 C16 C15 -37.0(3) . . . . ?
C4 N1 C16 C15 -150.3(2) . . . . ?
C13 C14 C15 C16 2.7(4) . . . . ?
C13 C14 C15 C17 -178.2(2) . . . . ?
C11 C16 C15 C14 -3.9(4) . . . . ?
N1 C16 C15 C14 179.2(2) . . . . ?
C11 C16 C15 C17 176.9(2) . . . . ?
N1 C16 C15 C17 0.0(4) . . . . ?
C18 C17 C15 C14 23.7(4) . . . . ?
C22 C17 C15 C14 -156.7(2) . . . . ?
C18 C17 C15 C16 -157.1(2) . . . . ?
C22 C17 C15 C16 22.4(4) . . . . ?
C6 C5 C10 C9 0.2(4) . . . . ?
C4 C5 C10 C9 -179.4(2) . . . . ?
C6 C5 C10 C11 177.3(2) . . . . ?
C4 C5 C10 C11 -2.2(4) . . . . ?
C8 C9 C10 C5 -1.6(4) . . . . ?
C8 C9 C10 C11 -178.6(2) . . . . ?
C16 C11 C10 C5 -16.2(4) . . . . ?
C12 C11 C10 C5 164.2(2) . . . . ?
C16 C11 C10 C9 160.8(2) . . . . ?
C12 C11 C10 C9 -18.8(4) . . . . ?
C25 C3 C2 C23 -3.5(4) . . . . ?
C4 C3 C2 C23 178.2(2) . . . . ?
C25 C3 C2 C1 179.7(2) . . . . ?
C4 C3 C2 C1 1.4(3) . . . . ?
O1 C23 C2 C3 -139.0(3) . . . . ?
O2 C23 C2 C3 42.7(4) . . . . ?
O1 C23 C2 C1 37.3(4) . . . . ?
O2 C23 C2 C1 -141.0(2) . . . . ?
N1 C1 C2 C3 -27.0(3) . . . . ?
C22 C1 C2 C3 -151.8(2) . . . . ?
N1 C1 C2 C23 156.0(2) . . . . ?
C22 C1 C2 C23 31.2(4) . . . . ?
C26 O4 C25 O3 11.6(4) . . . . ?
C26 O4 C25 C3 -167.7(2) . . . . ?
C2 C3 C25 O3 -136.3(3) . . . . ?
C4 C3 C25 O3 41.8(4) . . . . ?
C2 C3 C25 O4 43.0(4) . . . . ?
C4 C3 C25 O4 -138.9(2) . . . . ?
C15 C14 C13 C12 -0.1(4) . . . . ?
C15 C14 C13 C27 -179.1(2) . . . . ?
C18 C17 C22 C21 -3.6(4) . . . . ?
C15 C17 C22 C21 176.8(2) . . . . ?
C18 C17 C22 C1 173.8(2) . . . . ?
C15 C17 C22 C1 -5.8(4) . . . . ?
N1 C1 C22 C21 146.5(2) . . . . ?
C2 C1 C22 C21 -94.0(3) . . . . ?
N1 C1 C22 C17 -30.8(3) . . . . ?
C2 C1 C22 C17 88.6(3) . . . . ?
C17 C22 C21 C20 0.6(4) . . . . ?
C1 C22 C21 C20 -176.7(2) . . . . ?
C12 C13 C27 C29 0.7(4) . . . . ?
C14 C13 C27 C29 179.7(2) . . . . ?
C12 C13 C27 C28 120.2(3) . . . . ?
C14 C13 C27 C28 -60.8(3) . . . . ?
C12 C13 C27 C30 -120.3(3) . . . . ?
C14 C13 C27 C30 58.6(3) . . . . ?
C10 C5 C6 C7 2.3(4) . . . . ?
C4 C5 C6 C7 -178.2(2) . . . . ?
C10 C9 C8 C7 0.7(4) . . . . ?
C18 C19 C20 C21 -2.7(4) . . . . ?
C22 C21 C20 C19 2.6(4) . . . . ?
C14 C13 C12 C11 -1.2(4) . . . . ?
C27 C13 C12 C11 177.7(2) . . . . ?
C16 C11 C12 C13 0.0(4) . . . . ?
C10 C11 C12 C13 179.6(2) . . . . ?
C20 C19 C18 C17 -0.3(4) . . . . ?
C22 C17 C18 C19 3.5(4) . . . . ?
C15 C17 C18 C19 -177.0(2) . . . . ?
C9 C8 C7 C6 1.8(4) . . . . ?
C5 C6 C7 C8 -3.2(4) . . . . ?

_diffrn_measured_fraction_theta_max 0.998
_diffrn_reflns_theta_full        25.00
_diffrn_measured_fraction_theta_full 0.998
_refine_diff_density_max         0.197
_refine_diff_density_min         -0.232
_refine_diff_density_rms         0.054
_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: dichloromethane'
_database_code_depnum_ccdc_archive 'CCDC 1019909'
#######################################################################
#
#                 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_9APPHA

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
8-t-Butyl-1,2-diphenylbenzo[7,8]indolizino[6,5,4,3-def]phenanthridine
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C38 H29 N'
_chemical_formula_sum            'C38 H29 N'
_chemical_formula_weight         499.62

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           orthorhombic
_symmetry_space_group_name_H-M   Pbca

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

_cell_length_a                   8.784(2)
_cell_length_b                   20.520(5)
_cell_length_c                   29.114(7)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_volume                     5248(2)
_cell_formula_units_Z            8
_cell_measurement_temperature    93
_cell_measurement_reflns_used    12512
_cell_measurement_theta_min      2.7
_cell_measurement_theta_max      31.4

_exptl_crystal_description       Block
_exptl_crystal_colour            Yellow
_exptl_crystal_size_max          0.20
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.10
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.265
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             2112
_exptl_absorpt_coefficient_mu    0.072
_exptl_absorpt_correction_type   Multi-scan
_exptl_absorpt_correction_T_min  0.9857
_exptl_absorpt_correction_T_max  0.9928
_exptl_absorpt_process_details   'Jacobson, R. (1998) Private communication'

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      93(2)
_diffrn_radiation_wavelength     0.71075
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Rigaku Saturn724 CCD'
_diffrn_measurement_method       'omega scans'
_diffrn_detector_area_resol_mean 28.5714
_diffrn_reflns_number            32588
_diffrn_reflns_av_R_equivalents  0.0671
_diffrn_reflns_av_sigmaI/netI    0.0369
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -24
_diffrn_reflns_limit_k_max       24
_diffrn_reflns_limit_l_min       -32
_diffrn_reflns_limit_l_max       34
_diffrn_reflns_theta_min         2.71
_diffrn_reflns_theta_max         25.00
_reflns_number_total             4631
_reflns_number_gt                3997
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'RIGAKU CrystalClear'
_computing_cell_refinement       'RIGAKU CrystalClear'
_computing_data_reduction        'RIGAKU CrystalClear'
_computing_structure_solution    SIR-97
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    ORTEP-III
_computing_publication_material  ?

_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)+(0.0439P)²+3.2311P] 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_number_reflns         4631
_refine_ls_number_parameters     355
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0723
_refine_ls_R_factor_gt           0.0592
_refine_ls_wR_factor_ref         0.1272
_refine_ls_wR_factor_gt          0.1202
_refine_ls_goodness_of_fit_ref   1.143
_refine_ls_restrained_S_all      1.143
_refine_ls_shift/su_max          0.009
_refine_ls_shift/su_mean         0.002

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 0.61572(19) -0.05274(8) 0.37872(6) 0.0177(4) Uani 1 1 d . . .
C22 C 0.6246(2) 0.04706(10) 0.33355(7) 0.0187(5) Uani 1 1 d . . .
C13 C 1.0160(2) -0.12599(10) 0.31995(7) 0.0210(5) Uani 1 1 d . . .
C2 C 0.4228(2) 0.01411(9) 0.39622(7) 0.0194(5) Uani 1 1 d . . .
C21 C 0.5698(3) 0.10959(10) 0.32220(7) 0.0225(5) Uani 1 1 d . . .
H10 H 0.4844 0.1267 0.3382 0.027 Uiso 1 1 calc R . .
C3 C 0.4098(2) -0.04292(10) 0.42400(7) 0.0203(5) Uani 1 1 d . . .
C16 C 0.7466(2) -0.07766(10) 0.35840(6) 0.0176(4) Uani 1 1 d . . .
C10 C 0.7157(2) -0.17481(10) 0.40811(7) 0.0195(5) Uani 1 1 d . . .
C18 C 0.8200(3) 0.06074(10) 0.27546(7) 0.0233(5) Uani 1 1 d . . .
H7 H 0.9052 0.0443 0.2591 0.028 Uiso 1 1 calc R . .
C9 C 0.7648(3) -0.23663(10) 0.42398(7) 0.0238(5) Uani 1 1 d . . .
H4 H 0.8524 -0.2561 0.4107 0.029 Uiso 1 1 calc R . .
C24 C 0.3387(3) 0.12421(10) 0.42391(7) 0.0240(5) Uani 1 1 d . . .
H11 H 0.4222 0.1247 0.4447 0.029 Uiso 1 1 calc R . .
C15 C 0.8207(2) -0.04062(10) 0.32432(7) 0.0193(5) Uani 1 1 d . . .
C34 C 0.1436(3) -0.07862(10) 0.44279(7) 0.0251(5) Uani 1 1 d . . .
H20 H 0.1287 -0.0878 0.4111 0.030 Uiso 1 1 calc R . .
C1 C 0.5515(2) 0.00740(9) 0.36837(7) 0.0189(5) Uani 1 1 d . . .
C4 C 0.5313(2) -0.08395(9) 0.41270(7) 0.0188(5) Uani 1 1 d . . .
C11 C 0.7998(2) -0.13904(10) 0.37255(7) 0.0193(5) Uani 1 1 d . . .
C32 C 0.0442(2) -0.07480(10) 0.51951(7) 0.0226(5) Uani 1 1 d . . .
H18 H -0.0379 -0.0809 0.5403 0.027 Uiso 1 1 calc R . .
C31 C 0.1846(3) -0.05138(10) 0.53519(7) 0.0259(5) Uani 1 1 d . . .
H17 H 0.1992 -0.0424 0.5669 0.031 Uiso 1 1 calc R . .
C27 C 0.0918(3) 0.12309(11) 0.36448(8) 0.0277(5) Uani 1 1 d . . .
H14 H 0.0073 0.1227 0.3441 0.033 Uiso 1 1 calc R . .
C14 C 0.9556(2) -0.06625(10) 0.30588(7) 0.0208(5) Uani 1 1 d . . .
H6 H 1.0078 -0.0421 0.2829 0.025 Uiso 1 1 calc R . .
C35 C 1.1688(2) -0.14965(10) 0.30020(7) 0.0236(5) Uani 1 1 d . . .
C19 C 0.7624(3) 0.12140(10) 0.26420(7) 0.0253(5) Uani 1 1 d . . .
H8 H 0.8073 0.1460 0.2401 0.030 Uiso 1 1 calc R . .
C28 C 0.1881(2) 0.06950(10) 0.36664(7) 0.0244(5) Uani 1 1 d . . .
H15 H 0.1682 0.0324 0.3481 0.029 Uiso 1 1 calc R . .
C29 C 0.2843(2) -0.05472(9) 0.45749(7) 0.0200(5) Uani 1 1 d . . .
C17 C 0.7551(2) 0.02295(10) 0.31064(7) 0.0196(5) Uani 1 1 d . . .
C7 C 0.5577(3) -0.24159(10) 0.47791(7) 0.0239(5) Uani 1 1 d . . .
H2 H 0.5048 -0.2641 0.5016 0.029 Uiso 1 1 calc R . .
C8 C 0.6881(3) -0.26895(10) 0.45823(7) 0.0254(5) Uani 1 1 d . . .
H3 H 0.7238 -0.3101 0.4686 0.030 Uiso 1 1 calc R . .
C20 C 0.6382(3) 0.14631(10) 0.28825(8) 0.0252(5) Uani 1 1 d . . .
H9 H 0.6005 0.1886 0.2813 0.030 Uiso 1 1 calc R . .
C6 C 0.5064(3) -0.18185(10) 0.46282(7) 0.0220(5) Uani 1 1 d . . .
H1 H 0.4172 -0.1636 0.4761 0.026 Uiso 1 1 calc R . .
C25 C 0.2426(3) 0.17724(10) 0.42162(7) 0.0250(5) Uani 1 1 d . . .
H12 H 0.2612 0.2142 0.4405 0.030 Uiso 1 1 calc R . .
C26 C 0.1181(3) 0.17699(10) 0.39180(7) 0.0240(5) Uani 1 1 d . . .
H13 H 0.0520 0.2136 0.3903 0.029 Uiso 1 1 calc R . .
C12 C 0.9353(2) -0.16172(10) 0.35264(7) 0.0216(5) Uani 1 1 d . . .
H5 H 0.9735 -0.2030 0.3618 0.026 Uiso 1 1 calc R . .
C23 C 0.3144(2) 0.06970(10) 0.39595(7) 0.0196(5) Uani 1 1 d . . .
C30 C 0.3015(3) -0.04146(10) 0.50437(7) 0.0250(5) Uani 1 1 d . . .
H16 H 0.3961 -0.0252 0.5152 0.030 Uiso 1 1 calc R . .
C36 C 1.2870(3) -0.09502(11) 0.30470(8) 0.0284(5) Uani 1 1 d . . .
H21 H 1.3856 -0.1104 0.2932 0.043 Uiso 1 1 calc R . .
H22 H 1.2969 -0.0825 0.3370 0.043 Uiso 1 1 calc R . .
H23 H 1.2542 -0.0572 0.2867 0.043 Uiso 1 1 calc R . .
C37 C 1.1505(3) -0.16828(11) 0.24950(8) 0.0295(5) Uani 1 1 d . . .
H24 H 1.2476 -0.1848 0.2377 0.044 Uiso 1 1 calc R . .
H25 H 1.1197 -0.1298 0.2318 0.044 Uiso 1 1 calc R . .
H26 H 1.0725 -0.2022 0.2466 0.044 Uiso 1 1 calc R . .
C5 C 0.5832(2) -0.14726(9) 0.42814(7) 0.0190(5) Uani 1 1 d . . .
C33 C 0.0267(3) -0.08904(10) 0.47297(8) 0.0253(5) Uani 1 1 d . . .
H19 H -0.0672 -0.1061 0.4621 0.030 Uiso 1 1 calc R . .
C38 C 1.2300(3) -0.20920(12) 0.32572(8) 0.0350(6) Uani 1 1 d . . .
H27 H 1.1594 -0.2458 0.3218 0.052 Uiso 1 1 calc R . .
H28 H 1.2398 -0.1990 0.3585 0.052 Uiso 1 1 calc R . .
H29 H 1.3299 -0.2210 0.3133 0.052 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 C1 1.390(2) . ?
N1 C16 1.391(3) . ?
N1 C4 1.392(3) . ?
C22 C21 1.410(3) . ?
C22 C17 1.415(3) . ?
C22 C1 1.450(3) . ?
C13 C12 1.395(3) . ?
C13 C14 1.397(3) . ?
C13 C35 1.539(3) . ?
C2 C1 1.398(3) . ?
C2 C3 1.427(3) . ?
C2 C23 1.486(3) . ?
C21 C20 1.380(3) . ?
C21 H10 0.9500 . ?
C3 C4 1.399(3) . ?
C3 C29 1.492(3) . ?
C16 C11 1.405(3) . ?
C16 C15 1.409(3) . ?
C10 C9 1.417(3) . ?
C10 C5 1.419(3) . ?
C10 C11 1.469(3) . ?
C18 C19 1.383(3) . ?
C18 C17 1.405(3) . ?
C18 H7 0.9500 . ?
C9 C8 1.374(3) . ?
C9 H4 0.9500 . ?
C24 C25 1.379(3) . ?
C24 C23 1.400(3) . ?
C24 H11 0.9500 . ?
C15 C14 1.403(3) . ?
C15 C17 1.481(3) . ?
C34 C33 1.368(3) . ?
C34 C29 1.397(3) . ?
C34 H20 0.9500 . ?
C4 C5 1.448(3) . ?
C11 C12 1.403(3) . ?
C32 C33 1.395(3) . ?
C32 C31 1.400(3) . ?
C32 H18 0.9500 . ?
C31 C30 1.378(3) . ?
C31 H17 0.9500 . ?
C27 C26 1.382(3) . ?
C27 C28 1.389(3) . ?
C27 H14 0.9500 . ?
C14 H6 0.9500 . ?
C35 C38 1.528(3) . ?
C35 C37 1.533(3) . ?
C35 C36 1.533(3) . ?
C19 C20 1.394(3) . ?
C19 H8 0.9500 . ?
C28 C23 1.400(3) . ?
C28 H15 0.9500 . ?
C29 C30 1.400(3) . ?
C7 C6 1.378(3) . ?
C7 C8 1.398(3) . ?
C7 H2 0.9500 . ?
C8 H3 0.9500 . ?
C20 H9 0.9500 . ?
C6 C5 1.407(3) . ?
C6 H1 0.9500 . ?
C25 C26 1.396(3) . ?
C25 H12 0.9500 . ?
C26 H13 0.9500 . ?
C12 H5 0.9500 . ?
C30 H16 0.9500 . ?
C36 H21 0.9800 . ?
C36 H22 0.9800 . ?
C36 H23 0.9800 . ?
C37 H24 0.9800 . ?
C37 H25 0.9800 . ?
C37 H26 0.9800 . ?
C33 H19 0.9500 . ?
C38 H27 0.9800 . ?
C38 H28 0.9800 . ?
C38 H29 0.9800 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C1 N1 C16 124.73(17) . . ?
C1 N1 C4 110.28(16) . . ?
C16 N1 C4 124.99(17) . . ?
C21 C22 C17 118.98(19) . . ?
C21 C22 C1 121.56(19) . . ?
C17 C22 C1 119.46(18) . . ?
C12 C13 C14 117.91(19) . . ?
C12 C13 C35 122.18(19) . . ?
C14 C13 C35 119.89(19) . . ?
C1 C2 C3 108.22(18) . . ?
C1 C2 C23 126.21(18) . . ?
C3 C2 C23 125.53(19) . . ?
C20 C21 C22 121.1(2) . . ?
C20 C21 H10 119.5 . . ?
C22 C21 H10 119.5 . . ?
C4 C3 C2 107.41(18) . . ?
C4 C3 C29 128.32(18) . . ?
C2 C3 C29 124.24(18) . . ?
N1 C16 C11 118.67(18) . . ?
N1 C16 C15 118.89(18) . . ?
C11 C16 C15 122.44(19) . . ?
C9 C10 C5 118.18(19) . . ?
C9 C10 C11 121.59(19) . . ?
C5 C10 C11 120.22(18) . . ?
C19 C18 C17 121.4(2) . . ?
C19 C18 H7 119.3 . . ?
C17 C18 H7 119.3 . . ?
C8 C9 C10 121.3(2) . . ?
C8 C9 H4 119.4 . . ?
C10 C9 H4 119.4 . . ?
C25 C24 C23 120.6(2) . . ?
C25 C24 H11 119.7 . . ?
C23 C24 H11 119.7 . . ?
C14 C15 C16 117.21(19) . . ?
C14 C15 C17 123.78(19) . . ?
C16 C15 C17 119.01(18) . . ?
C33 C34 C29 121.5(2) . . ?
C33 C34 H20 119.3 . . ?
C29 C34 H20 119.3 . . ?
N1 C1 C2 106.84(17) . . ?
N1 C1 C22 118.06(18) . . ?
C2 C1 C22 135.10(19) . . ?
N1 C4 C3 107.24(17) . . ?
N1 C4 C5 117.76(18) . . ?
C3 C4 C5 134.99(19) . . ?
C12 C11 C16 117.27(18) . . ?
C12 C11 C10 123.53(18) . . ?
C16 C11 C10 119.17(19) . . ?
C33 C32 C31 119.1(2) . . ?
C33 C32 H18 120.5 . . ?
C31 C32 H18 120.5 . . ?
C30 C31 C32 119.6(2) . . ?
C30 C31 H17 120.2 . . ?
C32 C31 H17 120.2 . . ?
C26 C27 C28 120.4(2) . . ?
C26 C27 H14 119.8 . . ?
C28 C27 H14 119.8 . . ?
C13 C14 C15 122.50(19) . . ?
C13 C14 H6 118.7 . . ?
C15 C14 H6 118.7 . . ?
C38 C35 C37 107.80(18) . . ?
C38 C35 C36 107.77(19) . . ?
C37 C35 C36 109.61(18) . . ?
C38 C35 C13 112.15(18) . . ?
C37 C35 C13 110.30(18) . . ?
C36 C35 C13 109.16(17) . . ?
C18 C19 C20 119.8(2) . . ?
C18 C19 H8 120.1 . . ?
C20 C19 H8 120.1 . . ?
C27 C28 C23 120.5(2) . . ?
C27 C28 H15 119.7 . . ?
C23 C28 H15 119.7 . . ?
C34 C29 C30 117.55(19) . . ?
C34 C29 C3 120.72(18) . . ?
C30 C29 C3 121.72(19) . . ?
C18 C17 C22 118.62(19) . . ?
C18 C17 C15 121.61(19) . . ?
C22 C17 C15 119.77(18) . . ?
C6 C7 C8 119.6(2) . . ?
C6 C7 H2 120.2 . . ?
C8 C7 H2 120.2 . . ?
C9 C8 C7 120.3(2) . . ?
C9 C8 H3 119.8 . . ?
C7 C8 H3 119.8 . . ?
C21 C20 C19 120.0(2) . . ?
C21 C20 H9 120.0 . . ?
C19 C20 H9 120.0 . . ?
C7 C6 C5 121.4(2) . . ?
C7 C6 H1 119.3 . . ?
C5 C6 H1 119.3 . . ?
C24 C25 C26 120.5(2) . . ?
C24 C25 H12 119.8 . . ?
C26 C25 H12 119.8 . . ?
C27 C26 C25 119.5(2) . . ?
C27 C26 H13 120.3 . . ?
C25 C26 H13 120.3 . . ?
C13 C12 C11 122.59(19) . . ?
C13 C12 H5 118.7 . . ?
C11 C12 H5 118.7 . . ?
C28 C23 C24 118.55(19) . . ?
C28 C23 C2 120.59(18) . . ?
C24 C23 C2 120.84(19) . . ?
C31 C30 C29 121.7(2) . . ?
C31 C30 H16 119.2 . . ?
C29 C30 H16 119.2 . . ?
C35 C36 H21 109.5 . . ?
C35 C36 H22 109.5 . . ?
H21 C36 H22 109.5 . . ?
C35 C36 H23 109.5 . . ?
H21 C36 H23 109.5 . . ?
H22 C36 H23 109.5 . . ?
C35 C37 H24 109.5 . . ?
C35 C37 H25 109.5 . . ?
H24 C37 H25 109.5 . . ?
C35 C37 H26 109.5 . . ?
H24 C37 H26 109.5 . . ?
H25 C37 H26 109.5 . . ?
C6 C5 C10 119.16(19) . . ?
C6 C5 C4 121.64(19) . . ?
C10 C5 C4 119.19(18) . . ?
C34 C33 C32 120.5(2) . . ?
C34 C33 H19 119.7 . . ?
C32 C33 H19 119.7 . . ?
C35 C38 H27 109.5 . . ?
C35 C38 H28 109.5 . . ?
H27 C38 H28 109.5 . . ?
C35 C38 H29 109.5 . . ?
H27 C38 H29 109.5 . . ?
H28 C38 H29 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
C17 C22 C21 C20 2.2(3) . . . . ?
C1 C22 C21 C20 -178.5(2) . . . . ?
C1 C2 C3 C4 0.0(2) . . . . ?
C23 C2 C3 C4 177.92(19) . . . . ?
C1 C2 C3 C29 -178.46(18) . . . . ?
C23 C2 C3 C29 -0.5(3) . . . . ?
C1 N1 C16 C11 179.36(18) . . . . ?
C4 N1 C16 C11 0.2(3) . . . . ?
C1 N1 C16 C15 -0.9(3) . . . . ?
C4 N1 C16 C15 180.00(18) . . . . ?
C5 C10 C9 C8 -0.8(3) . . . . ?
C11 C10 C9 C8 178.03(19) . . . . ?
N1 C16 C15 C14 177.63(17) . . . . ?
C11 C16 C15 C14 -2.6(3) . . . . ?
N1 C16 C15 C17 -1.2(3) . . . . ?
C11 C16 C15 C17 178.58(18) . . . . ?
C16 N1 C1 C2 -179.71(17) . . . . ?
C4 N1 C1 C2 -0.5(2) . . . . ?
C16 N1 C1 C22 0.7(3) . . . . ?
C4 N1 C1 C22 179.94(17) . . . . ?
C3 C2 C1 N1 0.3(2) . . . . ?
C23 C2 C1 N1 -177.62(19) . . . . ?
C3 C2 C1 C22 179.8(2) . . . . ?
C23 C2 C1 C22 1.9(4) . . . . ?
C21 C22 C1 N1 -177.75(18) . . . . ?
C17 C22 C1 N1 1.6(3) . . . . ?
C21 C22 C1 C2 2.8(4) . . . . ?
C17 C22 C1 C2 -177.8(2) . . . . ?
C1 N1 C4 C3 0.5(2) . . . . ?
C16 N1 C4 C3 179.70(17) . . . . ?
C1 N1 C4 C5 -179.34(17) . . . . ?
C16 N1 C4 C5 -0.1(3) . . . . ?
C2 C3 C4 N1 -0.3(2) . . . . ?
C29 C3 C4 N1 178.09(19) . . . . ?
C2 C3 C4 C5 179.5(2) . . . . ?
C29 C3 C4 C5 -2.2(4) . . . . ?
N1 C16 C11 C12 -177.66(17) . . . . ?
C15 C16 C11 C12 2.6(3) . . . . ?
N1 C16 C11 C10 0.1(3) . . . . ?
C15 C16 C11 C10 -179.64(18) . . . . ?
C9 C10 C11 C12 -1.8(3) . . . . ?
C5 C10 C11 C12 177.04(18) . . . . ?
C9 C10 C11 C16 -179.44(19) . . . . ?
C5 C10 C11 C16 -0.6(3) . . . . ?
C33 C32 C31 C30 1.4(3) . . . . ?
C12 C13 C14 C15 1.9(3) . . . . ?
C35 C13 C14 C15 -176.78(18) . . . . ?
C16 C15 C14 C13 0.3(3) . . . . ?
C17 C15 C14 C13 179.04(19) . . . . ?
C12 C13 C35 C38 -8.9(3) . . . . ?
C14 C13 C35 C38 169.7(2) . . . . ?
C12 C13 C35 C37 111.2(2) . . . . ?
C14 C13 C35 C37 -70.1(2) . . . . ?
C12 C13 C35 C36 -128.3(2) . . . . ?
C14 C13 C35 C36 50.3(3) . . . . ?
C17 C18 C19 C20 0.5(3) . . . . ?
C26 C27 C28 C23 -1.0(3) . . . . ?
C33 C34 C29 C30 -0.3(3) . . . . ?
C33 C34 C29 C3 -179.27(19) . . . . ?
C4 C3 C29 C34 -96.4(3) . . . . ?
C2 C3 C29 C34 81.7(3) . . . . ?
C4 C3 C29 C30 84.6(3) . . . . ?
C2 C3 C29 C30 -97.2(3) . . . . ?
C19 C18 C17 C22 2.4(3) . . . . ?
C19 C18 C17 C15 -177.06(19) . . . . ?
C21 C22 C17 C18 -3.7(3) . . . . ?
C1 C22 C17 C18 176.98(19) . . . . ?
C21 C22 C17 C15 175.78(18) . . . . ?
C1 C22 C17 C15 -3.6(3) . . . . ?
C14 C15 C17 C18 4.1(3) . . . . ?
C16 C15 C17 C18 -177.17(19) . . . . ?
C14 C15 C17 C22 -175.32(19) . . . . ?
C16 C15 C17 C22 3.4(3) . . . . ?
C10 C9 C8 C7 0.8(3) . . . . ?
C6 C7 C8 C9 -0.1(3) . . . . ?
C22 C21 C20 C19 0.8(3) . . . . ?
C18 C19 C20 C21 -2.1(3) . . . . ?
C8 C7 C6 C5 -0.5(3) . . . . ?
C23 C24 C25 C26 0.9(3) . . . . ?
C28 C27 C26 C25 0.1(3) . . . . ?
C24 C25 C26 C27 0.0(3) . . . . ?
C14 C13 C12 C11 -2.0(3) . . . . ?
C35 C13 C12 C11 176.71(19) . . . . ?
C16 C11 C12 C13 -0.2(3) . . . . ?
C10 C11 C12 C13 -177.89(19) . . . . ?
C27 C28 C23 C24 1.8(3) . . . . ?
C27 C28 C23 C2 -176.25(19) . . . . ?
C25 C24 C23 C28 -1.8(3) . . . . ?
C25 C24 C23 C2 176.27(19) . . . . ?
C1 C2 C23 C28 88.9(3) . . . . ?
C3 C2 C23 C28 -88.7(3) . . . . ?
C1 C2 C23 C24 -89.2(3) . . . . ?
C3 C2 C23 C24 93.3(3) . . . . ?
C32 C31 C30 C29 -0.5(3) . . . . ?
C34 C29 C30 C31 -0.1(3) . . . . ?
C3 C29 C30 C31 178.92(19) . . . . ?
C7 C6 C5 C10 0.5(3) . . . . ?
C7 C6 C5 C4 -178.90(19) . . . . ?
C9 C10 C5 C6 0.2(3) . . . . ?
C11 C10 C5 C6 -178.68(18) . . . . ?
C9 C10 C5 C4 179.60(18) . . . . ?
C11 C10 C5 C4 0.7(3) . . . . ?
N1 C4 C5 C6 179.00(18) . . . . ?
C3 C4 C5 C6 -0.7(4) . . . . ?
N1 C4 C5 C10 -0.4(3) . . . . ?
C3 C4 C5 C10 179.9(2) . . . . ?
C29 C34 C33 C32 1.2(3) . . . . ?
C31 C32 C33 C34 -1.7(3) . . . . ?

_diffrn_measured_fraction_theta_max 0.999
_diffrn_reflns_theta_full        25.00
_diffrn_measured_fraction_theta_full 0.999
_refine_diff_density_max         0.244
_refine_diff_density_min         -0.233
_refine_diff_density_rms         0.044
_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: dichloromethane'
_database_code_depnum_ccdc_archive 'CCDC 1019910'
#######################################################################
#
#                 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_9APDMCPA

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
"Dimethyl 4,4'-(8-t-butylbenzo[7,8]indolizino[6,5,4,3-def]phenanthridine-1,2-diyl)dibenzoate"
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C42 H33 N O4'
_chemical_formula_weight         615.69

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   Pbca

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

_cell_length_a                   9.666(3)
_cell_length_b                   22.449(6)
_cell_length_c                   29.445(8)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_volume                     6389(3)
_cell_formula_units_Z            8
_cell_measurement_temperature    93
_cell_measurement_reflns_used    16492
_cell_measurement_theta_min      2.7
_cell_measurement_theta_max      31.6

_exptl_crystal_description       Block
_exptl_crystal_colour            Colorless
_exptl_crystal_size_max          0.30
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.10
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.280
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             2592
_exptl_absorpt_coefficient_mu    0.082
_exptl_absorpt_correction_type   Multi-scan
_exptl_absorpt_correction_T_min  0.9759
_exptl_absorpt_correction_T_max  0.9919
_exptl_absorpt_process_details   'Jacobson, R. (1998) Private communication'

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      93(2)
_diffrn_radiation_wavelength     0.71075
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Rigaku Saturn724 CCD'
_diffrn_measurement_method       'omega scans'
_diffrn_detector_area_resol_mean 28.5714
_diffrn_reflns_number            39918
_diffrn_reflns_av_R_equivalents  0.0851
_diffrn_reflns_av_sigmaI/netI    0.0454
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -23
_diffrn_reflns_limit_k_max       26
_diffrn_reflns_limit_l_min       -34
_diffrn_reflns_limit_l_max       35
_diffrn_reflns_theta_min         2.68
_diffrn_reflns_theta_max         25.00
_reflns_number_total             5622
_reflns_number_gt                5262
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'RIGAKU CrystalClear'
_computing_cell_refinement       'RIGAKU CrystalClear'
_computing_data_reduction        'RIGAKU CrystalClear'
_computing_structure_solution    SIR-97
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    ORTEP-III
_computing_publication_material  ?

_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)+(0.0280P)²+8.0148P] 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_number_reflns         5622
_refine_ls_number_parameters     429
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0865
_refine_ls_R_factor_gt           0.0799
_refine_ls_wR_factor_ref         0.1455
_refine_ls_wR_factor_gt          0.1425
_refine_ls_goodness_of_fit_ref   1.301
_refine_ls_restrained_S_all      1.301
_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
O2 O 0.4770(2) 0.09850(9) 0.00932(6) 0.0214(5) Uani 1 1 d . . .
C36 C 0.5982(3) -0.09752(12) 0.17721(9) 0.0152(6) Uani 1 1 d . . .
H27 H 0.5062 -0.0829 0.1794 0.018 Uiso 1 1 calc R . .
O3 O 0.7003(2) -0.23922(9) 0.08961(7) 0.0273(5) Uani 1 1 d . . .
O4 O 0.9212(2) -0.23337(9) 0.11290(7) 0.0275(5) Uani 1 1 d . . .
O1 O 0.6578(2) 0.03769(9) -0.00385(7) 0.0232(5) Uani 1 1 d . . .
C14 C 0.6679(3) -0.04166(12) 0.36345(9) 0.0144(6) Uani 1 1 d . . .
C21 C 0.5690(3) 0.10207(12) 0.42504(9) 0.0137(6) Uani 1 1 d . . .
C27 C 0.6071(3) 0.04468(12) 0.16716(9) 0.0147(6) Uani 1 1 d . . .
C20 C 0.5365(3) 0.13749(13) 0.38759(9) 0.0172(6) Uani 1 1 d . . .
H9 H 0.5042 0.1769 0.3927 0.021 Uiso 1 1 calc R . .
C39 C 0.8669(3) -0.13937(13) 0.16995(10) 0.0196(7) Uani 1 1 d . . .
H29 H 0.9594 -0.1532 0.1671 0.023 Uiso 1 1 calc R . .
N1 N 0.6158(2) 0.03786(10) 0.29244(7) 0.0140(5) Uani 1 1 d . . .
C12 C 0.5970(3) 0.05866(12) 0.33665(9) 0.0147(6) Uani 1 1 d . . .
C18 C 0.7286(3) -0.11965(12) 0.30951(10) 0.0162(6) Uani 1 1 d . . .
H8 H 0.7434 -0.1322 0.2791 0.019 Uiso 1 1 calc R . .
C3 C 0.6668(3) -0.02153(12) 0.23428(9) 0.0138(6) Uani 1 1 d . . .
C15 C 0.6873(3) -0.08362(13) 0.39849(9) 0.0175(6) Uani 1 1 d . . .
H5 H 0.6736 -0.0718 0.4291 0.021 Uiso 1 1 calc R . .
C4 C 0.6641(3) -0.01856(12) 0.28136(9) 0.0132(6) Uani 1 1 d . . .
C26 C 0.6037(3) 0.08426(13) 0.51006(9) 0.0212(7) Uani 1 1 d . . .
H17 H 0.5376 0.0512 0.5097 0.032 Uiso 1 1 calc R . .
H18 H 0.6015 0.1037 0.5398 0.032 Uiso 1 1 calc R . .
H19 H 0.6970 0.0690 0.5042 0.032 Uiso 1 1 calc R . .
C37 C 0.6278(3) -0.14327(12) 0.14726(9) 0.0157(6) Uani 1 1 d . . .
H28 H 0.5563 -0.1600 0.1292 0.019 Uiso 1 1 calc R . .
C35 C 0.7019(3) -0.07247(12) 0.20437(9) 0.0132(6) Uani 1 1 d . . .
C16 C 0.7257(3) -0.14165(13) 0.38924(10) 0.0184(6) Uani 1 1 d . . .
H6 H 0.7376 -0.1692 0.4134 0.022 Uiso 1 1 calc R . .
C40 C 0.8361(3) -0.09389(12) 0.20022(10) 0.0176(6) Uani 1 1 d . . .
H30 H 0.9077 -0.0772 0.2183 0.021 Uiso 1 1 calc R . .
C23 C 0.5647(3) 0.12956(13) 0.47310(9) 0.0168(6) Uani 1 1 d . . .
C38 C 0.7626(3) -0.16475(12) 0.14367(9) 0.0163(6) Uani 1 1 d . . .
C1 C 0.5893(3) 0.07081(12) 0.25354(10) 0.0172(6) Uani 1 1 d . . .
C31 C 0.4694(3) 0.06403(12) 0.10012(10) 0.0177(6) Uani 1 1 d . . .
H22 H 0.3829 0.0740 0.0868 0.021 Uiso 1 1 calc R . .
C10 C 0.5206(3) 0.15507(13) 0.30280(10) 0.0204(7) Uani 1 1 d . . .
C24 C 0.6691(3) 0.18159(14) 0.47453(10) 0.0244(7) Uani 1 1 d . . .
H11 H 0.7619 0.1667 0.4674 0.037 Uiso 1 1 calc R . .
H12 H 0.6694 0.1993 0.5050 0.037 Uiso 1 1 calc R . .
H13 H 0.6424 0.2118 0.4522 0.037 Uiso 1 1 calc R . .
C32 C 0.4800(3) 0.05768(12) 0.14696(9) 0.0174(6) Uani 1 1 d . . .
H23 H 0.4001 0.0622 0.1654 0.021 Uiso 1 1 calc R . .
C29 C 0.7119(3) 0.04143(12) 0.09251(10) 0.0172(6) Uani 1 1 d . . .
H21 H 0.7907 0.0348 0.0739 0.021 Uiso 1 1 calc R . .
C19 C 0.6882(3) -0.06064(12) 0.31797(9) 0.0142(6) Uani 1 1 d . . .
C30 C 0.5852(3) 0.05576(12) 0.07271(9) 0.0157(6) Uani 1 1 d . . .
C13 C 0.6243(3) 0.01996(12) 0.37322(9) 0.0143(6) Uani 1 1 d . . .
C22 C 0.6109(3) 0.04331(12) 0.41732(9) 0.0153(6) Uani 1 1 d . . .
H10 H 0.6310 0.0185 0.4426 0.018 Uiso 1 1 calc R . .
C41 C 0.7887(3) -0.21556(13) 0.11247(10) 0.0194(7) Uani 1 1 d . . .
C11 C 0.5494(3) 0.11758(13) 0.34300(9) 0.0173(6) Uani 1 1 d . . .
C33 C 0.5789(3) 0.06186(12) 0.02248(10) 0.0175(6) Uani 1 1 d . . .
C17 C 0.7472(3) -0.15977(13) 0.34448(9) 0.0170(6) Uani 1 1 d . . .
H7 H 0.7745 -0.1996 0.3381 0.020 Uiso 1 1 calc R . .
C28 C 0.7229(3) 0.03687(13) 0.13948(10) 0.0179(6) Uani 1 1 d . . .
H20 H 0.8101 0.0284 0.1529 0.021 Uiso 1 1 calc R . .
C6 C 0.5235(4) 0.16932(14) 0.22103(10) 0.0284(8) Uani 1 1 d . . .
H1 H 0.5428 0.1546 0.1914 0.034 Uiso 1 1 calc R . .
C25 C 0.4189(3) 0.15322(13) 0.48363(10) 0.0219(7) Uani 1 1 d . . .
H14 H 0.3922 0.1824 0.4605 0.033 Uiso 1 1 calc R . .
H15 H 0.4188 0.1722 0.5136 0.033 Uiso 1 1 calc R . .
H16 H 0.3530 0.1201 0.4835 0.033 Uiso 1 1 calc R . .
C5 C 0.5439(3) 0.13207(13) 0.25875(9) 0.0190(7) Uani 1 1 d . . .
C34 C 0.4649(3) 0.10804(15) -0.03940(10) 0.0260(7) Uani 1 1 d . . .
H24 H 0.5552 0.1196 -0.0517 0.039 Uiso 1 1 calc R . .
H25 H 0.3976 0.1398 -0.0452 0.039 Uiso 1 1 calc R . .
H26 H 0.4339 0.0712 -0.0540 0.039 Uiso 1 1 calc R . .
C7 C 0.4760(4) 0.22656(15) 0.22613(11) 0.0380(10) Uani 1 1 d . . .
H2 H 0.4622 0.2510 0.2002 0.046 Uiso 1 1 calc R . .
C8 C 0.4481(4) 0.24884(15) 0.26923(11) 0.0396(10) Uani 1 1 d . . .
H3 H 0.4136 0.2882 0.2728 0.047 Uiso 1 1 calc R . .
C2 C 0.6188(3) 0.03374(12) 0.21681(9) 0.0160(6) Uani 1 1 d . . .
C9 C 0.4709(4) 0.21341(14) 0.30694(11) 0.0303(8) Uani 1 1 d . . .
H4 H 0.4524 0.2290 0.3363 0.036 Uiso 1 1 calc R . .
C42 C 0.9514(4) -0.28608(15) 0.08608(12) 0.0375(9) Uani 1 1 d . . .
H31 H 0.8928 -0.3191 0.0963 0.056 Uiso 1 1 calc R . .
H32 H 1.0489 -0.2969 0.0899 0.056 Uiso 1 1 calc R . .
H33 H 0.9327 -0.2778 0.0540 0.056 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
O2 C33 1.341(3) . ?
O2 C34 1.455(3) . ?
C36 C37 1.384(4) . ?
C36 C35 1.400(4) . ?
C36 H27 0.9500 . ?
O3 C41 1.211(4) . ?
O4 C41 1.341(4) . ?
O4 C42 1.452(4) . ?
O1 C33 1.215(3) . ?
C14 C15 1.410(4) . ?
C14 C19 1.419(4) . ?
C14 C13 1.474(4) . ?
C21 C20 1.395(4) . ?
C21 C22 1.399(4) . ?
C21 C23 1.544(4) . ?
C27 C28 1.395(4) . ?
C27 C32 1.396(4) . ?
C27 C2 1.487(4) . ?
C20 C11 1.393(4) . ?
C20 H9 0.9500 . ?
C39 C40 1.388(4) . ?
C39 C38 1.393(4) . ?
C39 H29 0.9500 . ?
N1 C1 1.387(4) . ?
N1 C4 1.389(3) . ?
N1 C12 1.395(3) . ?
C12 C13 1.408(4) . ?
C12 C11 1.413(4) . ?
C18 C17 1.380(4) . ?
C18 C19 1.403(4) . ?
C18 H8 0.9500 . ?
C3 C4 1.388(4) . ?
C3 C2 1.421(4) . ?
C3 C35 1.483(4) . ?
C15 C16 1.382(4) . ?
C15 H5 0.9500 . ?
C4 C19 1.452(4) . ?
C26 C23 1.537(4) . ?
C26 H17 0.9800 . ?
C26 H18 0.9800 . ?
C26 H19 0.9800 . ?
C37 C38 1.393(4) . ?
C37 H28 0.9500 . ?
C35 C40 1.389(4) . ?
C16 C17 1.395(4) . ?
C16 H6 0.9500 . ?
C40 H30 0.9500 . ?
C23 C25 1.537(4) . ?
C23 C24 1.545(4) . ?
C38 C41 1.486(4) . ?
C1 C2 1.394(4) . ?
C1 C5 1.452(4) . ?
C31 C32 1.390(4) . ?
C31 C30 1.393(4) . ?
C31 H22 0.9500 . ?
C10 C9 1.400(4) . ?
C10 C5 1.414(4) . ?
C10 C11 1.479(4) . ?
C24 H11 0.9800 . ?
C24 H12 0.9800 . ?
C24 H13 0.9800 . ?
C32 H23 0.9500 . ?
C29 C28 1.391(4) . ?
C29 C30 1.394(4) . ?
C29 H21 0.9500 . ?
C30 C33 1.487(4) . ?
C13 C22 1.406(4) . ?
C22 H10 0.9500 . ?
C17 H7 0.9500 . ?
C28 H20 0.9500 . ?
C6 C7 1.373(4) . ?
C6 C5 1.404(4) . ?
C6 H1 0.9500 . ?
C25 H14 0.9800 . ?
C25 H15 0.9800 . ?
C25 H16 0.9800 . ?
C34 H24 0.9800 . ?
C34 H25 0.9800 . ?
C34 H26 0.9800 . ?
C7 C8 1.390(4) . ?
C7 H2 0.9500 . ?
C8 C9 1.383(4) . ?
C8 H3 0.9500 . ?
C9 H4 0.9500 . ?
C42 H31 0.9800 . ?
C42 H32 0.9800 . ?
C42 H33 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
C33 O2 C34 115.7(2) . . ?
C37 C36 C35 121.0(3) . . ?
C37 C36 H27 119.5 . . ?
C35 C36 H27 119.5 . . ?
C41 O4 C42 115.4(3) . . ?
C15 C14 C19 118.1(3) . . ?
C15 C14 C13 121.5(3) . . ?
C19 C14 C13 120.4(2) . . ?
C20 C21 C22 118.3(3) . . ?
C20 C21 C23 119.4(2) . . ?
C22 C21 C23 122.3(2) . . ?
C28 C27 C32 118.9(3) . . ?
C28 C27 C2 119.5(3) . . ?
C32 C27 C2 121.4(3) . . ?
C11 C20 C21 122.8(3) . . ?
C11 C20 H9 118.6 . . ?
C21 C20 H9 118.6 . . ?
C40 C39 C38 120.2(3) . . ?
C40 C39 H29 119.9 . . ?
C38 C39 H29 119.9 . . ?
C1 N1 C4 110.8(2) . . ?
C1 N1 C12 124.6(2) . . ?
C4 N1 C12 124.6(2) . . ?
N1 C12 C13 118.9(2) . . ?
N1 C12 C11 118.6(2) . . ?
C13 C12 C11 122.5(3) . . ?
C17 C18 C19 121.3(3) . . ?
C17 C18 H8 119.3 . . ?
C19 C18 H8 119.3 . . ?
C4 C3 C2 108.3(2) . . ?
C4 C3 C35 129.4(3) . . ?
C2 C3 C35 122.2(2) . . ?
C16 C15 C14 121.4(3) . . ?
C16 C15 H5 119.3 . . ?
C14 C15 H5 119.3 . . ?
C3 C4 N1 106.5(2) . . ?
C3 C4 C19 135.0(3) . . ?
N1 C4 C19 118.2(2) . . ?
C23 C26 H17 109.5 . . ?
C23 C26 H18 109.5 . . ?
H17 C26 H18 109.5 . . ?
C23 C26 H19 109.5 . . ?
H17 C26 H19 109.5 . . ?
H18 C26 H19 109.5 . . ?
C36 C37 C38 119.9(3) . . ?
C36 C37 H28 120.0 . . ?
C38 C37 H28 120.0 . . ?
C40 C35 C36 118.6(3) . . ?
C40 C35 C3 122.2(2) . . ?
C36 C35 C3 119.0(2) . . ?
C15 C16 C17 120.1(3) . . ?
C15 C16 H6 120.0 . . ?
C17 C16 H6 120.0 . . ?
C39 C40 C35 120.8(3) . . ?
C39 C40 H30 119.6 . . ?
C35 C40 H30 119.6 . . ?
C26 C23 C25 108.1(2) . . ?
C26 C23 C21 112.2(2) . . ?
C25 C23 C21 110.3(2) . . ?
C26 C23 C24 108.7(2) . . ?
C25 C23 C24 109.4(2) . . ?
C21 C23 C24 108.0(2) . . ?
C39 C38 C37 119.6(3) . . ?
C39 C38 C41 122.3(3) . . ?
C37 C38 C41 118.1(3) . . ?
N1 C1 C2 106.5(2) . . ?
N1 C1 C5 118.3(2) . . ?
C2 C1 C5 135.2(3) . . ?
C32 C31 C30 120.1(3) . . ?
C32 C31 H22 119.9 . . ?
C30 C31 H22 119.9 . . ?
C9 C10 C5 118.4(3) . . ?
C9 C10 C11 121.8(3) . . ?
C5 C10 C11 119.7(3) . . ?
C23 C24 H11 109.5 . . ?
C23 C24 H12 109.5 . . ?
H11 C24 H12 109.5 . . ?
C23 C24 H13 109.5 . . ?
H11 C24 H13 109.5 . . ?
H12 C24 H13 109.5 . . ?
C31 C32 C27 120.6(3) . . ?
C31 C32 H23 119.7 . . ?
C27 C32 H23 119.7 . . ?
C28 C29 C30 120.0(3) . . ?
C28 C29 H21 120.0 . . ?
C30 C29 H21 120.0 . . ?
C18 C19 C14 119.3(3) . . ?
C18 C19 C4 121.8(3) . . ?
C14 C19 C4 118.9(2) . . ?
C31 C30 C29 119.7(3) . . ?
C31 C30 C33 122.1(3) . . ?
C29 C30 C33 118.3(3) . . ?
C22 C13 C12 117.3(2) . . ?
C22 C13 C14 123.8(2) . . ?
C12 C13 C14 118.9(2) . . ?
C21 C22 C13 121.9(3) . . ?
C21 C22 H10 119.1 . . ?
C13 C22 H10 119.1 . . ?
O3 C41 O4 123.3(3) . . ?
O3 C41 C38 124.1(3) . . ?
O4 C41 C38 112.6(3) . . ?
C20 C11 C12 117.0(3) . . ?
C20 C11 C10 123.7(3) . . ?
C12 C11 C10 119.2(2) . . ?
O1 C33 O2 123.4(3) . . ?
O1 C33 C30 124.6(3) . . ?
O2 C33 C30 112.0(2) . . ?
C18 C17 C16 119.7(3) . . ?
C18 C17 H7 120.2 . . ?
C16 C17 H7 120.2 . . ?
C29 C28 C27 120.7(3) . . ?
C29 C28 H20 119.6 . . ?
C27 C28 H20 119.6 . . ?
C7 C6 C5 121.2(3) . . ?
C7 C6 H1 119.4 . . ?
C5 C6 H1 119.4 . . ?
C23 C25 H14 109.5 . . ?
C23 C25 H15 109.5 . . ?
H14 C25 H15 109.5 . . ?
C23 C25 H16 109.5 . . ?
H14 C25 H16 109.5 . . ?
H15 C25 H16 109.5 . . ?
C6 C5 C10 119.0(3) . . ?
C6 C5 C1 121.5(3) . . ?
C10 C5 C1 119.4(3) . . ?
O2 C34 H24 109.5 . . ?
O2 C34 H25 109.5 . . ?
H24 C34 H25 109.5 . . ?
O2 C34 H26 109.5 . . ?
H24 C34 H26 109.5 . . ?
H25 C34 H26 109.5 . . ?
C6 C7 C8 120.1(3) . . ?
C6 C7 H2 120.0 . . ?
C8 C7 H2 120.0 . . ?
C9 C8 C7 119.7(3) . . ?
C9 C8 H3 120.2 . . ?
C7 C8 H3 120.2 . . ?
C1 C2 C3 107.9(2) . . ?
C1 C2 C27 130.4(3) . . ?
C3 C2 C27 121.7(2) . . ?
C8 C9 C10 121.5(3) . . ?
C8 C9 H4 119.3 . . ?
C10 C9 H4 119.3 . . ?
O4 C42 H31 109.5 . . ?
O4 C42 H32 109.5 . . ?
H31 C42 H32 109.5 . . ?
O4 C42 H33 109.5 . . ?
H31 C42 H33 109.5 . . ?
H32 C42 H33 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
C22 C21 C20 C11 -2.6(4) . . . . ?
C23 C21 C20 C11 174.3(3) . . . . ?
C1 N1 C12 C13 178.3(3) . . . . ?
C4 N1 C12 C13 -1.9(4) . . . . ?
C1 N1 C12 C11 -1.0(4) . . . . ?
C4 N1 C12 C11 178.8(3) . . . . ?
C19 C14 C15 C16 0.4(4) . . . . ?
C13 C14 C15 C16 178.8(3) . . . . ?
C2 C3 C4 N1 -0.3(3) . . . . ?
C35 C3 C4 N1 -176.1(3) . . . . ?
C2 C3 C4 C19 173.8(3) . . . . ?
C35 C3 C4 C19 -2.1(5) . . . . ?
C1 N1 C4 C3 -0.6(3) . . . . ?
C12 N1 C4 C3 179.6(2) . . . . ?
C1 N1 C4 C19 -175.8(2) . . . . ?
C12 N1 C4 C19 4.3(4) . . . . ?
C35 C36 C37 C38 -0.4(4) . . . . ?
C37 C36 C35 C40 0.9(4) . . . . ?
C37 C36 C35 C3 177.0(2) . . . . ?
C4 C3 C35 C40 -70.7(4) . . . . ?
C2 C3 C35 C40 114.0(3) . . . . ?
C4 C3 C35 C36 113.4(3) . . . . ?
C2 C3 C35 C36 -61.9(4) . . . . ?
C14 C15 C16 C17 0.4(4) . . . . ?
C38 C39 C40 C35 -0.9(4) . . . . ?
C36 C35 C40 C39 -0.3(4) . . . . ?
C3 C35 C40 C39 -176.2(3) . . . . ?
C20 C21 C23 C26 -179.8(3) . . . . ?
C22 C21 C23 C26 -3.0(4) . . . . ?
C20 C21 C23 C25 59.5(3) . . . . ?
C22 C21 C23 C25 -123.6(3) . . . . ?
C20 C21 C23 C24 -60.0(3) . . . . ?
C22 C21 C23 C24 116.8(3) . . . . ?
C40 C39 C38 C37 1.4(4) . . . . ?
C40 C39 C38 C41 -176.9(3) . . . . ?
C36 C37 C38 C39 -0.8(4) . . . . ?
C36 C37 C38 C41 177.6(2) . . . . ?
C4 N1 C1 C2 1.3(3) . . . . ?
C12 N1 C1 C2 -178.9(3) . . . . ?
C4 N1 C1 C5 -177.2(3) . . . . ?
C12 N1 C1 C5 2.6(4) . . . . ?
C30 C31 C32 C27 1.8(4) . . . . ?
C28 C27 C32 C31 -1.4(4) . . . . ?
C2 C27 C32 C31 -175.9(3) . . . . ?
C17 C18 C19 C14 0.8(4) . . . . ?
C17 C18 C19 C4 -178.0(3) . . . . ?
C15 C14 C19 C18 -1.0(4) . . . . ?
C13 C14 C19 C18 -179.4(3) . . . . ?
C15 C14 C19 C4 177.9(3) . . . . ?
C13 C14 C19 C4 -0.5(4) . . . . ?
C3 C4 C19 C18 2.4(5) . . . . ?
N1 C4 C19 C18 175.9(3) . . . . ?
C3 C4 C19 C14 -176.4(3) . . . . ?
N1 C4 C19 C14 -2.9(4) . . . . ?
C32 C31 C30 C29 -0.4(4) . . . . ?
C32 C31 C30 C33 179.8(3) . . . . ?
C28 C29 C30 C31 -1.6(4) . . . . ?
C28 C29 C30 C33 178.3(3) . . . . ?
N1 C12 C13 C22 176.8(2) . . . . ?
C11 C12 C13 C22 -4.0(4) . . . . ?
N1 C12 C13 C14 -1.8(4) . . . . ?
C11 C12 C13 C14 177.4(3) . . . . ?
C15 C14 C13 C22 6.0(4) . . . . ?
C19 C14 C13 C22 -175.6(3) . . . . ?
C15 C14 C13 C12 -175.5(3) . . . . ?
C19 C14 C13 C12 2.9(4) . . . . ?
C20 C21 C22 C13 1.6(4) . . . . ?
C23 C21 C22 C13 -175.3(3) . . . . ?
C12 C13 C22 C21 1.6(4) . . . . ?
C14 C13 C22 C21 -179.9(3) . . . . ?
C42 O4 C41 O3 -3.8(4) . . . . ?
C42 O4 C41 C38 175.0(3) . . . . ?
C39 C38 C41 O3 178.9(3) . . . . ?
C37 C38 C41 O3 0.7(4) . . . . ?
C39 C38 C41 O4 0.1(4) . . . . ?
C37 C38 C41 O4 -178.1(2) . . . . ?
C21 C20 C11 C12 0.4(4) . . . . ?
C21 C20 C11 C10 -177.7(3) . . . . ?
N1 C12 C11 C20 -177.8(3) . . . . ?
C13 C12 C11 C20 3.0(4) . . . . ?
N1 C12 C11 C10 0.4(4) . . . . ?
C13 C12 C11 C10 -178.8(3) . . . . ?
C9 C10 C11 C20 -3.2(5) . . . . ?
C5 C10 C11 C20 176.5(3) . . . . ?
C9 C10 C11 C12 178.8(3) . . . . ?
C5 C10 C11 C12 -1.5(4) . . . . ?
C34 O2 C33 O1 0.1(4) . . . . ?
C34 O2 C33 C30 178.8(2) . . . . ?
C31 C30 C33 O1 -155.0(3) . . . . ?
C29 C30 C33 O1 25.2(4) . . . . ?
C31 C30 C33 O2 26.4(4) . . . . ?
C29 C30 C33 O2 -153.5(3) . . . . ?
C19 C18 C17 C16 0.0(4) . . . . ?
C15 C16 C17 C18 -0.6(4) . . . . ?
C30 C29 C28 C27 2.0(4) . . . . ?
C32 C27 C28 C29 -0.6(4) . . . . ?
C2 C27 C28 C29 174.0(3) . . . . ?
C7 C6 C5 C10 -2.7(5) . . . . ?
C7 C6 C5 C1 177.7(3) . . . . ?
C9 C10 C5 C6 3.2(5) . . . . ?
C11 C10 C5 C6 -176.4(3) . . . . ?
C9 C10 C5 C1 -177.2(3) . . . . ?
C11 C10 C5 C1 3.2(4) . . . . ?
N1 C1 C5 C6 175.9(3) . . . . ?
C2 C1 C5 C6 -2.0(6) . . . . ?
N1 C1 C5 C10 -3.6(4) . . . . ?
C2 C1 C5 C10 178.4(3) . . . . ?
C5 C6 C7 C8 0.4(6) . . . . ?
C6 C7 C8 C9 1.2(6) . . . . ?
N1 C1 C2 C3 -1.4(3) . . . . ?
C5 C1 C2 C3 176.7(3) . . . . ?
N1 C1 C2 C27 178.7(3) . . . . ?
C5 C1 C2 C27 -3.1(6) . . . . ?
C4 C3 C2 C1 1.1(3) . . . . ?
C35 C3 C2 C1 177.3(3) . . . . ?
C4 C3 C2 C27 -179.0(3) . . . . ?
C35 C3 C2 C27 -2.8(4) . . . . ?
C28 C27 C2 C1 124.2(3) . . . . ?
C32 C27 C2 C1 -61.3(4) . . . . ?
C28 C27 C2 C3 -55.6(4) . . . . ?
C32 C27 C2 C3 118.8(3) . . . . ?
C7 C8 C9 C10 -0.6(6) . . . . ?
C5 C10 C9 C8 -1.7(5) . . . . ?
C11 C10 C9 C8 178.0(3) . . . . ?

_diffrn_measured_fraction_theta_max 0.999
_diffrn_reflns_theta_full        25.00
_diffrn_measured_fraction_theta_full 0.999
_refine_diff_density_max         0.226
_refine_diff_density_min         -0.268
_refine_diff_density_rms         0.051
_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: dichloromethane'
_database_code_depnum_ccdc_archive 'CCDC 1019911'
