# Electronic Supplementary Material (ESI) for Organic Chemistry Frontiers.
# This journal is © the Partner Organisations 2017

####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_a
_audit_block_doi                 10.5517/ccdc.csd.cc1ntgzx
_database_code_depnum_ccdc_archive 'CCDC 1543830'
_audit_update_record             
;
2017-04-13 deposited with the CCDC.
2017-09-22 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
9b-(2-bromobenzyl)-5-methyl-5,9b-dihydropyrrolizino[3,2-b]indol-10(4aH)-one
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C21 H17 Br N2 O'
_chemical_formula_weight         196.64

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Br Br -0.2901 2.4595 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

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

_cell_length_a                   8.7889(18)
_cell_length_b                   8.9182(18)
_cell_length_c                   22.444(5)
_cell_angle_alpha                90.00
_cell_angle_beta                 91.02(3)
_cell_angle_gamma                90.00
_cell_volume                     1758.9(6)
_cell_formula_units_Z            8
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    3402
_cell_measurement_theta_min      2.4574
_cell_measurement_theta_max      27.9404
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          ?
_exptl_crystal_size_mid          ?
_exptl_crystal_size_min          ?
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.485
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             800
_exptl_absorpt_coefficient_mu    2.348
_exptl_absorpt_correction_type   ?
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?

_exptl_special_details           
; 
 ? 
;
_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  Multi-scan
_diffrn_measurement_method       dtprofit.ref
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            20845
_diffrn_reflns_av_R_equivalents  0.0557
_diffrn_reflns_av_sigmaI/netI    0.0505
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_l_min       -27
_diffrn_reflns_limit_l_max       29
_diffrn_reflns_theta_min         2.46
_diffrn_reflns_theta_max         28.02
_reflns_number_total             4152
_reflns_number_gt                2752
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    ?
_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)+(0.1483P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         4152
_refine_ls_number_parameters     227
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1190
_refine_ls_R_factor_gt           0.0742
_refine_ls_wR_factor_ref         0.2675
_refine_ls_wR_factor_gt          0.2136
_refine_ls_goodness_of_fit_ref   1.095
_refine_ls_restrained_S_all      1.095
_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
Br1 Br 0.41630(8) 1.12294(7) 0.10020(3) 0.0717(3) Uani 1 1 d . . .
O1 O 0.6074(4) 0.4762(4) 0.07638(14) 0.0482(8) Uani 1 1 d . . .
N1 N 0.2794(5) 0.7463(5) 0.19323(17) 0.0479(10) Uani 1 1 d . . .
N2 N 0.5261(4) 0.6305(4) 0.21381(18) 0.0402(9) Uani 1 1 d . . .
C1 C 0.1968(5) 0.6476(5) 0.1578(2) 0.0403(10) Uani 1 1 d . . .
C2 C 0.0483(6) 0.5970(6) 0.1626(3) 0.0554(13) Uani 1 1 d . . .
H2 H -0.0121 0.6277 0.1939 0.067 Uiso 1 1 calc R . .
C3 C -0.0074(6) 0.5000(7) 0.1197(3) 0.0611(14) Uani 1 1 d . . .
H3 H -0.1062 0.4639 0.1229 0.073 Uiso 1 1 calc R . .
C4 C 0.0780(6) 0.4546(7) 0.0722(3) 0.0594(14) Uani 1 1 d . . .
H4 H 0.0361 0.3913 0.0433 0.071 Uiso 1 1 calc R . .
C5 C 0.2260(6) 0.5036(6) 0.0676(2) 0.0498(11) Uani 1 1 d . . .
H5 H 0.2853 0.4718 0.0361 0.060 Uiso 1 1 calc R . .
C6 C 0.2855(5) 0.5995(5) 0.1098(2) 0.0380(9) Uani 1 1 d . . .
C7 C 0.4382(5) 0.7408(5) 0.17836(19) 0.0411(10) Uani 1 1 d . . .
H7 H 0.4854 0.8403 0.1794 0.049 Uiso 1 1 calc R . .
C8 C 0.4401(5) 0.6701(5) 0.11451(19) 0.0392(10) Uani 1 1 d . . .
C9 C 0.5582(5) 0.5440(5) 0.11837(19) 0.0384(9) Uani 1 1 d . . .
C10 C 0.5927(5) 0.5200(5) 0.18127(19) 0.0417(10) Uani 1 1 d . . .
C11 C 0.6727(6) 0.4259(7) 0.2192(2) 0.0540(12) Uani 1 1 d . . .
H11 H 0.7291 0.3420 0.2087 0.065 Uiso 1 1 calc R . .
C12 C 0.6514(6) 0.4829(7) 0.2769(2) 0.0586(13) Uani 1 1 d . . .
H12 H 0.6913 0.4426 0.3120 0.070 Uiso 1 1 calc R . .
C13 C 0.5613(6) 0.6085(6) 0.2723(2) 0.0498(12) Uani 1 1 d . . .
H13 H 0.5300 0.6680 0.3037 0.060 Uiso 1 1 calc R . .
C14 C 0.2285(7) 0.8006(9) 0.2494(3) 0.0762(18) Uani 1 1 d . . .
H14A H 0.1250 0.8340 0.2454 0.114 Uiso 1 1 calc R . .
H14B H 0.2917 0.8827 0.2622 0.114 Uiso 1 1 calc R . .
H14C H 0.2346 0.7214 0.2784 0.114 Uiso 1 1 calc R . .
C15 C 0.4684(5) 0.7785(5) 0.06297(19) 0.0415(10) Uani 1 1 d . . .
H15A H 0.4755 0.7202 0.0266 0.050 Uiso 1 1 calc R . .
H15B H 0.3803 0.8432 0.0586 0.050 Uiso 1 1 calc R . .
C16 C 0.6067(6) 0.8753(5) 0.0681(2) 0.0429(10) Uani 1 1 d . . .
C17 C 0.7497(6) 0.8162(6) 0.0573(2) 0.0516(12) Uani 1 1 d . . .
H17 H 0.7579 0.7148 0.0483 0.062 Uiso 1 1 calc R . .
C18 C 0.8804(7) 0.9023(7) 0.0595(3) 0.0604(14) Uani 1 1 d . . .
H18 H 0.9749 0.8578 0.0543 0.072 Uiso 1 1 calc R . .
C19 C 0.8702(7) 1.0554(7) 0.0694(3) 0.0636(14) Uani 1 1 d . . .
H19 H 0.9572 1.1145 0.0683 0.076 Uiso 1 1 calc R . .
C20 C 0.7335(8) 1.1191(6) 0.0807(2) 0.0598(15) Uani 1 1 d . . .
H20 H 0.7265 1.2214 0.0881 0.072 Uiso 1 1 calc R . .
C21 C 0.6024(6) 1.0284(6) 0.0810(2) 0.0523(12) Uani 1 1 d . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Br1 C21 1.897(6) . ?
O1 C9 1.206(5) . ?
N1 C1 1.384(6) . ?
N1 C14 1.430(7) . ?
N1 C7 1.442(6) . ?
N2 C13 1.357(6) . ?
N2 C10 1.365(6) . ?
N2 C7 1.474(6) . ?
C1 C2 1.387(7) . ?
C1 C6 1.408(6) . ?
C2 C3 1.378(8) . ?
C3 C4 1.375(8) . ?
C4 C5 1.378(7) . ?
C5 C6 1.372(6) . ?
C6 C8 1.500(6) . ?
C7 C8 1.566(6) . ?
C8 C15 1.531(6) . ?
C8 C9 1.532(6) . ?
C9 C10 1.454(6) . ?
C10 C11 1.379(7) . ?
C11 C12 1.407(8) . ?
C12 C13 1.374(8) . ?
C15 C16 1.493(6) . ?
C16 C17 1.388(7) . ?
C16 C21 1.396(6) . ?
C17 C18 1.382(8) . ?
C18 C19 1.386(8) . ?
C19 C20 1.356(9) . ?
C20 C21 1.408(8) . ?

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 C14 123.6(5) . . ?
C1 N1 C7 110.2(3) . . ?
C14 N1 C7 122.3(4) . . ?
C13 N2 C10 108.7(4) . . ?
C13 N2 C7 136.6(4) . . ?
C10 N2 C7 114.7(4) . . ?
N1 C1 C2 130.4(5) . . ?
N1 C1 C6 110.0(4) . . ?
C2 C1 C6 119.6(4) . . ?
C3 C2 C1 118.3(5) . . ?
C4 C3 C2 122.3(5) . . ?
C3 C4 C5 119.6(5) . . ?
C6 C5 C4 119.7(5) . . ?
C5 C6 C1 120.6(4) . . ?
C5 C6 C8 130.1(4) . . ?
C1 C6 C8 109.3(4) . . ?
N1 C7 N2 113.5(4) . . ?
N1 C7 C8 104.6(4) . . ?
N2 C7 C8 102.2(3) . . ?
C6 C8 C15 111.8(4) . . ?
C6 C8 C9 107.9(4) . . ?
C15 C8 C9 112.8(4) . . ?
C6 C8 C7 102.1(3) . . ?
C15 C8 C7 116.2(4) . . ?
C9 C8 C7 105.2(3) . . ?
O1 C9 C10 127.8(4) . . ?
O1 C9 C8 125.1(4) . . ?
C10 C9 C8 107.0(4) . . ?
N2 C10 C11 109.2(4) . . ?
N2 C10 C9 109.2(4) . . ?
C11 C10 C9 141.6(5) . . ?
C10 C11 C12 105.9(5) . . ?
C13 C12 C11 108.1(4) . . ?
N2 C13 C12 108.2(4) . . ?
C16 C15 C8 116.7(4) . . ?
C17 C16 C21 115.8(5) . . ?
C17 C16 C15 120.3(4) . . ?
C21 C16 C15 123.8(5) . . ?
C18 C17 C16 122.5(5) . . ?
C17 C18 C19 119.8(6) . . ?
C20 C19 C18 120.2(5) . . ?
C19 C20 C21 119.2(5) . . ?
C16 C21 C20 122.4(5) . . ?
C16 C21 Br1 120.5(4) . . ?
C20 C21 Br1 117.1(4) . . ?

_diffrn_measured_fraction_theta_max 0.976
_diffrn_reflns_theta_full        28.02
_diffrn_measured_fraction_theta_full 0.976
_refine_diff_density_max         0.591
_refine_diff_density_min         -0.711
_refine_diff_density_rms         0.123
_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: Dichloromethane / hexane'
####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_a_CCDC1
_database_code_depnum_ccdc_archive 'CCDC 1542588'
_audit_update_record             
;
2017-04-06 deposited with the CCDC.
2017-09-22 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C30 H28 N4 O2'
_chemical_formula_weight         476.56

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 '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)/n  '

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

_cell_length_a                   9.8465(5)
_cell_length_b                   26.3558(14)
_cell_length_c                   9.9725(5)
_cell_angle_alpha                90.00
_cell_angle_beta                 104.267(2)
_cell_angle_gamma                90.00
_cell_volume                     2508.2(2)
_cell_formula_units_Z            4
_cell_measurement_temperature    292(2)
_cell_measurement_reflns_used    9988
_cell_measurement_theta_min      3.35
_cell_measurement_theta_max      68.37

_exptl_crystal_description       block
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.20
_exptl_crystal_size_mid          0.18
_exptl_crystal_size_min          0.16
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.262
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1008
_exptl_absorpt_coefficient_mu    0.640
_exptl_absorpt_correction_type   none
_exptl_absorpt_correction_T_min  0.8826
_exptl_absorpt_correction_T_max  0.9045
_exptl_absorpt_process_details   ?

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      292(2)
_diffrn_radiation_wavelength     1.54178
_diffrn_radiation_type           CuK\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            27797
_diffrn_reflns_av_R_equivalents  0.0304
_diffrn_reflns_av_sigmaI/netI    0.0192
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -31
_diffrn_reflns_limit_k_max       31
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_theta_min         3.35
_diffrn_reflns_theta_max         68.42
_reflns_number_total             4559
_reflns_number_gt                4017
_reflns_threshold_expression     >2sigma(I)

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

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

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0581P)²+0.4497P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         4559
_refine_ls_number_parameters     329
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0474
_refine_ls_R_factor_gt           0.0420
_refine_ls_wR_factor_ref         0.1155
_refine_ls_wR_factor_gt          0.1109
_refine_ls_goodness_of_fit_ref   1.033
_refine_ls_restrained_S_all      1.033
_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
C14 C 0.02002(15) 0.04272(6) 0.19698(18) 0.0644(4) Uani 1 1 d . . .
H14A H -0.0571 0.0606 0.1383 0.097 Uiso 1 1 calc R . .
H14B H -0.0045 0.0328 0.2806 0.097 Uiso 1 1 calc R . .
H14C H 0.0410 0.0131 0.1499 0.097 Uiso 1 1 calc R . .
O1 O 0.31332(12) 0.00729(4) 0.29544(12) 0.0697(3) Uani 1 1 d . . .
O2 O 0.23612(15) 0.76317(4) 0.83293(14) 0.0848(4) Uani 1 1 d . . .
N1 N 0.12507(13) 0.16728(4) 0.21998(13) 0.0571(3) Uani 1 1 d . . .
N2 N 0.26027(11) 0.12542(4) 0.42850(11) 0.0488(3) Uani 1 1 d . . .
N3 N 0.33682(16) 0.92348(5) 0.71340(16) 0.0713(4) Uani 1 1 d . . .
N4 N 0.33209(12) 0.88612(4) 0.93620(12) 0.0558(3) Uani 1 1 d . . .
C1 C 0.20656(16) 0.18092(6) 0.00429(16) 0.0661(4) Uani 1 1 d . . .
H1 H 0.1981 0.2161 0.0045 0.079 Uiso 1 1 calc R . .
C2 C 0.25180(19) 0.15630(8) -0.09950(17) 0.0776(5) Uani 1 1 d . . .
H2 H 0.2745 0.1754 -0.1694 0.093 Uiso 1 1 calc R . .
C3 C 0.26399(19) 0.10448(8) -0.10187(16) 0.0747(5) Uani 1 1 d . . .
H3 H 0.2947 0.0889 -0.1728 0.090 Uiso 1 1 calc R . .
C4 C 0.23061(16) 0.07519(6) 0.00145(15) 0.0600(4) Uani 1 1 d . . .
H4 H 0.2376 0.0400 -0.0003 0.072 Uiso 1 1 calc R . .
C5 C 0.18687(12) 0.09914(5) 0.10667(13) 0.0458(3) Uani 1 1 d . . .
C6 C 0.17415(13) 0.15167(5) 0.10801(14) 0.0494(3) Uani 1 1 d . . .
C7 C 0.14812(12) 0.07724(5) 0.23228(13) 0.0449(3) Uani 1 1 d . . .
C8 C 0.27745(13) 0.04963(5) 0.32146(14) 0.0477(3) Uani 1 1 d . . .
C9 C 0.34204(13) 0.08272(5) 0.43262(13) 0.0477(3) Uani 1 1 d . . .
C10 C 0.13164(13) 0.12604(5) 0.31486(14) 0.0487(3) Uani 1 1 d . . .
H10 H 0.0473 0.1245 0.3503 0.058 Uiso 1 1 calc R . .
C11 C 0.45629(15) 0.08726(6) 0.54558(15) 0.0585(4) Uani 1 1 d . . .
H11 H 0.5290 0.0641 0.5739 0.070 Uiso 1 1 calc R . .
C12 C 0.44060(18) 0.13332(7) 0.60804(16) 0.0679(4) Uani 1 1 d . . .
H12 H 0.5022 0.1466 0.6862 0.082 Uiso 1 1 calc R . .
C13 C 0.31893(17) 0.15605(6) 0.53507(15) 0.0633(4) Uani 1 1 d . . .
H13 H 0.2836 0.1870 0.5557 0.076 Uiso 1 1 calc R . .
C15 C 0.11793(19) 0.21965(6) 0.2598(2) 0.0782(5) Uani 1 1 d . . .
H15A H 0.2111 0.2330 0.2917 0.117 Uiso 1 1 calc R . .
H15B H 0.0701 0.2219 0.3327 0.117 Uiso 1 1 calc R . .
H15C H 0.0679 0.2390 0.1815 0.117 Uiso 1 1 calc R . .
C16 C 0.1451(2) 0.92596(8) 0.4955(2) 0.0826(6) Uani 1 1 d . . .
H16 H 0.1437 0.9611 0.4865 0.099 Uiso 1 1 calc R . .
C17 C 0.0566(2) 0.89569(11) 0.3990(2) 0.0946(7) Uani 1 1 d . . .
H17 H -0.0050 0.9109 0.3239 0.113 Uiso 1 1 calc R . .
C18 C 0.05687(19) 0.84409(10) 0.41078(18) 0.0867(6) Uani 1 1 d . . .
H18 H -0.0042 0.8248 0.3442 0.104 Uiso 1 1 calc R . .
C19 C 0.14816(15) 0.82012(7) 0.52203(16) 0.0659(4) Uani 1 1 d . . .
H19 H 0.1484 0.7850 0.5306 0.079 Uiso 1 1 calc R . .
C20 C 0.23807(13) 0.84965(5) 0.61902(14) 0.0513(3) Uani 1 1 d . . .
C21 C 0.23667(15) 0.90215(6) 0.60677(16) 0.0587(4) Uani 1 1 d . . .
C22 C 0.34746(13) 0.83404(5) 0.74728(14) 0.0503(3) Uani 1 1 d . . .
C23 C 0.27462(15) 0.80702(5) 0.84670(15) 0.0569(3) Uani 1 1 d . . .
C24 C 0.26213(15) 0.84269(6) 0.95212(15) 0.0580(4) Uani 1 1 d . . .
C25 C 0.20962(19) 0.84869(8) 1.06835(17) 0.0767(5) Uani 1 1 d . . .
H25 H 0.1572 0.8252 1.1037 0.092 Uiso 1 1 calc R . .
C26 C 0.2504(2) 0.89643(8) 1.12147(18) 0.0833(5) Uani 1 1 d . . .
H26 H 0.2296 0.9108 1.1993 0.100 Uiso 1 1 calc R . .
C27 C 0.32667(18) 0.91898(7) 1.03973(18) 0.0731(5) Uani 1 1 d . . .
H27 H 0.3674 0.9510 1.0529 0.088 Uiso 1 1 calc R . .
C28 C 0.3583(2) 0.97701(6) 0.7354(3) 0.0956(7) Uani 1 1 d . . .
H28A H 0.3618 0.9931 0.6499 0.143 Uiso 1 1 calc R . .
H28B H 0.4451 0.9827 0.8029 0.143 Uiso 1 1 calc R . .
H28C H 0.2825 0.9911 0.7682 0.143 Uiso 1 1 calc R . .
C29 C 0.46592(16) 0.80226(6) 0.71632(18) 0.0702(4) Uani 1 1 d . . .
H29A H 0.4292 0.7703 0.6771 0.105 Uiso 1 1 calc R . .
H29B H 0.5363 0.7964 0.8005 0.105 Uiso 1 1 calc R . .
H29C H 0.5067 0.8201 0.6519 0.105 Uiso 1 1 calc R . .
C30 C 0.39450(14) 0.88615(5) 0.81556(16) 0.0573(4) Uani 1 1 d . . .
H30 H 0.4969 0.8887 0.8446 0.069 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
C14 C7 1.5244(18) . ?
C14 H14A 0.9600 . ?
C14 H14B 0.9600 . ?
C14 H14C 0.9600 . ?
O1 C8 1.2174(16) . ?
O2 C23 1.2133(17) . ?
N1 C6 1.3841(18) . ?
N1 C10 1.4320(17) . ?
N1 C15 1.4427(19) . ?
N2 C13 1.3461(18) . ?
N2 C9 1.3785(16) . ?
N2 C10 1.4769(17) . ?
N3 C21 1.379(2) . ?
N3 C30 1.429(2) . ?
N3 C28 1.436(2) . ?
N4 C27 1.3587(19) . ?
N4 C24 1.3652(19) . ?
N4 C30 1.4797(19) . ?
C1 C2 1.385(3) . ?
C1 C6 1.389(2) . ?
C1 H1 0.9300 . ?
C2 C3 1.372(3) . ?
C2 H2 0.9300 . ?
C3 C4 1.390(2) . ?
C3 H3 0.9300 . ?
C4 C5 1.381(2) . ?
C4 H4 0.9300 . ?
C5 C6 1.3904(19) . ?
C5 C7 1.5111(17) . ?
C7 C8 1.5441(17) . ?
C7 C10 1.5571(18) . ?
C8 C9 1.4307(19) . ?
C9 C11 1.3872(19) . ?
C10 H10 0.9800 . ?
C11 C12 1.390(2) . ?
C11 H11 0.9300 . ?
C12 C13 1.376(2) . ?
C12 H12 0.9300 . ?
C13 H13 0.9300 . ?
C15 H15A 0.9600 . ?
C15 H15B 0.9600 . ?
C15 H15C 0.9600 . ?
C16 C17 1.381(3) . ?
C16 C21 1.395(2) . ?
C16 H16 0.9300 . ?
C17 C18 1.365(3) . ?
C17 H17 0.9300 . ?
C18 C19 1.395(2) . ?
C18 H18 0.9300 . ?
C19 C20 1.379(2) . ?
C19 H19 0.9300 . ?
C20 C21 1.389(2) . ?
C20 C22 1.5121(19) . ?
C22 C29 1.5281(19) . ?
C22 C23 1.5346(19) . ?
C22 C30 1.5521(19) . ?
C23 C24 1.438(2) . ?
C24 C25 1.390(2) . ?
C25 C26 1.385(3) . ?
C25 H25 0.9300 . ?
C26 C27 1.373(3) . ?
C26 H26 0.9300 . ?
C27 H27 0.9300 . ?
C28 H28A 0.9600 . ?
C28 H28B 0.9600 . ?
C28 H28C 0.9600 . ?
C29 H29A 0.9600 . ?
C29 H29B 0.9600 . ?
C29 H29C 0.9600 . ?
C30 H30 0.9800 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C7 C14 H14A 109.5 . . ?
C7 C14 H14B 109.5 . . ?
H14A C14 H14B 109.5 . . ?
C7 C14 H14C 109.5 . . ?
H14A C14 H14C 109.5 . . ?
H14B C14 H14C 109.5 . . ?
C6 N1 C10 109.84(10) . . ?
C6 N1 C15 123.84(13) . . ?
C10 N1 C15 122.79(13) . . ?
C13 N2 C9 109.40(12) . . ?
C13 N2 C10 135.98(11) . . ?
C9 N2 C10 114.59(10) . . ?
C21 N3 C30 110.60(12) . . ?
C21 N3 C28 124.68(16) . . ?
C30 N3 C28 123.35(16) . . ?
C27 N4 C24 109.31(14) . . ?
C27 N4 C30 136.01(14) . . ?
C24 N4 C30 114.68(11) . . ?
C2 C1 C6 118.14(15) . . ?
C2 C1 H1 120.9 . . ?
C6 C1 H1 120.9 . . ?
C3 C2 C1 121.67(15) . . ?
C3 C2 H2 119.2 . . ?
C1 C2 H2 119.2 . . ?
C2 C3 C4 120.17(16) . . ?
C2 C3 H3 119.9 . . ?
C4 C3 H3 119.9 . . ?
C5 C4 C3 118.95(15) . . ?
C5 C4 H4 120.5 . . ?
C3 C4 H4 120.5 . . ?
C4 C5 C6 120.54(13) . . ?
C4 C5 C7 130.16(12) . . ?
C6 C5 C7 109.30(11) . . ?
N1 C6 C1 128.73(13) . . ?
N1 C6 C5 110.73(11) . . ?
C1 C6 C5 120.52(14) . . ?
C5 C7 C14 113.59(11) . . ?
C5 C7 C8 108.46(10) . . ?
C14 C7 C8 111.69(11) . . ?
C5 C7 C10 101.74(10) . . ?
C14 C7 C10 115.28(11) . . ?
C8 C7 C10 105.27(10) . . ?
O1 C8 C9 128.83(12) . . ?
O1 C8 C7 123.42(12) . . ?
C9 C8 C7 107.75(10) . . ?
N2 C9 C11 107.74(12) . . ?
N2 C9 C8 109.26(11) . . ?
C11 C9 C8 142.99(13) . . ?
N1 C10 N2 113.96(11) . . ?
N1 C10 C7 105.73(11) . . ?
N2 C10 C7 102.43(9) . . ?
N1 C10 H10 111.4 . . ?
N2 C10 H10 111.4 . . ?
C7 C10 H10 111.4 . . ?
C9 C11 C12 106.36(13) . . ?
C9 C11 H11 126.8 . . ?
C12 C11 H11 126.8 . . ?
C13 C12 C11 108.75(14) . . ?
C13 C12 H12 125.6 . . ?
C11 C12 H12 125.6 . . ?
N2 C13 C12 107.74(13) . . ?
N2 C13 H13 126.1 . . ?
C12 C13 H13 126.1 . . ?
N1 C15 H15A 109.5 . . ?
N1 C15 H15B 109.5 . . ?
H15A C15 H15B 109.5 . . ?
N1 C15 H15C 109.5 . . ?
H15A C15 H15C 109.5 . . ?
H15B C15 H15C 109.5 . . ?
C17 C16 C21 117.88(18) . . ?
C17 C16 H16 121.1 . . ?
C21 C16 H16 121.1 . . ?
C18 C17 C16 121.86(18) . . ?
C18 C17 H17 119.1 . . ?
C16 C17 H17 119.1 . . ?
C17 C18 C19 120.45(19) . . ?
C17 C18 H18 119.8 . . ?
C19 C18 H18 119.8 . . ?
C20 C19 C18 118.59(18) . . ?
C20 C19 H19 120.7 . . ?
C18 C19 H19 120.7 . . ?
C19 C20 C21 120.64(14) . . ?
C19 C20 C22 129.78(14) . . ?
C21 C20 C22 109.58(12) . . ?
N3 C21 C20 110.40(13) . . ?
N3 C21 C16 129.00(16) . . ?
C20 C21 C16 120.57(16) . . ?
C20 C22 C29 113.47(12) . . ?
C20 C22 C23 108.90(11) . . ?
C29 C22 C23 112.19(12) . . ?
C20 C22 C30 101.75(11) . . ?
C29 C22 C30 114.43(12) . . ?
C23 C22 C30 105.29(11) . . ?
O2 C23 C24 128.67(15) . . ?
O2 C23 C22 123.47(14) . . ?
C24 C23 C22 107.86(11) . . ?
N4 C24 C25 107.67(14) . . ?
N4 C24 C23 109.06(13) . . ?
C25 C24 C23 143.19(16) . . ?
C26 C25 C24 106.86(17) . . ?
C26 C25 H25 126.6 . . ?
C24 C25 H25 126.6 . . ?
C27 C26 C25 108.39(16) . . ?
C27 C26 H26 125.8 . . ?
C25 C26 H26 125.8 . . ?
N4 C27 C26 107.75(16) . . ?
N4 C27 H27 126.1 . . ?
C26 C27 H27 126.1 . . ?
N3 C28 H28A 109.5 . . ?
N3 C28 H28B 109.5 . . ?
H28A C28 H28B 109.5 . . ?
N3 C28 H28C 109.5 . . ?
H28A C28 H28C 109.5 . . ?
H28B C28 H28C 109.5 . . ?
C22 C29 H29A 109.5 . . ?
C22 C29 H29B 109.5 . . ?
H29A C29 H29B 109.5 . . ?
C22 C29 H29C 109.5 . . ?
H29A C29 H29C 109.5 . . ?
H29B C29 H29C 109.5 . . ?
N3 C30 N4 114.09(12) . . ?
N3 C30 C22 105.86(12) . . ?
N4 C30 C22 102.56(11) . . ?
N3 C30 H30 111.3 . . ?
N4 C30 H30 111.3 . . ?
C22 C30 H30 111.3 . . ?

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
C6 C1 C2 C3 0.4(2) . . . . ?
C1 C2 C3 C4 0.0(3) . . . . ?
C2 C3 C4 C5 -0.8(2) . . . . ?
C3 C4 C5 C6 1.1(2) . . . . ?
C3 C4 C5 C7 -178.23(13) . . . . ?
C10 N1 C6 C1 -168.82(13) . . . . ?
C15 N1 C6 C1 -9.6(2) . . . . ?
C10 N1 C6 C5 12.44(15) . . . . ?
C15 N1 C6 C5 171.70(14) . . . . ?
C2 C1 C6 N1 -178.73(14) . . . . ?
C2 C1 C6 C5 -0.1(2) . . . . ?
C4 C5 C6 N1 178.21(12) . . . . ?
C7 C5 C6 N1 -2.35(14) . . . . ?
C4 C5 C6 C1 -0.64(19) . . . . ?
C7 C5 C6 C1 178.79(12) . . . . ?
C4 C5 C7 C14 -63.62(18) . . . . ?
C6 C5 C7 C14 117.01(12) . . . . ?
C4 C5 C7 C8 61.19(17) . . . . ?
C6 C5 C7 C8 -118.17(11) . . . . ?
C4 C5 C7 C10 171.86(13) . . . . ?
C6 C5 C7 C10 -7.50(13) . . . . ?
C5 C7 C8 O1 -79.32(15) . . . . ?
C14 C7 C8 O1 46.61(18) . . . . ?
C10 C7 C8 O1 172.41(13) . . . . ?
C5 C7 C8 C9 100.08(12) . . . . ?
C14 C7 C8 C9 -133.99(12) . . . . ?
C10 C7 C8 C9 -8.19(13) . . . . ?
C13 N2 C9 C11 -0.43(15) . . . . ?
C10 N2 C9 C11 -178.78(11) . . . . ?
C13 N2 C9 C8 178.44(11) . . . . ?
C10 N2 C9 C8 0.10(15) . . . . ?
O1 C8 C9 N2 -175.42(14) . . . . ?
C7 C8 C9 N2 5.23(14) . . . . ?
O1 C8 C9 C11 2.8(3) . . . . ?
C7 C8 C9 C11 -176.56(17) . . . . ?
C6 N1 C10 N2 94.94(13) . . . . ?
C15 N1 C10 N2 -64.58(17) . . . . ?
C6 N1 C10 C7 -16.77(14) . . . . ?
C15 N1 C10 C7 -176.28(13) . . . . ?
C13 N2 C10 N1 63.36(19) . . . . ?
C9 N2 C10 N1 -118.88(12) . . . . ?
C13 N2 C10 C7 177.05(15) . . . . ?
C9 N2 C10 C7 -5.20(13) . . . . ?
C5 C7 C10 N1 14.29(12) . . . . ?
C14 C7 C10 N1 -109.09(13) . . . . ?
C8 C7 C10 N1 127.36(11) . . . . ?
C5 C7 C10 N2 -105.31(10) . . . . ?
C14 C7 C10 N2 131.31(12) . . . . ?
C8 C7 C10 N2 7.76(12) . . . . ?
N2 C9 C11 C12 0.00(16) . . . . ?
C8 C9 C11 C12 -178.23(17) . . . . ?
C9 C11 C12 C13 0.42(18) . . . . ?
C9 N2 C13 C12 0.69(17) . . . . ?
C10 N2 C13 C12 178.53(14) . . . . ?
C11 C12 C13 N2 -0.69(19) . . . . ?
C21 C16 C17 C18 0.2(3) . . . . ?
C16 C17 C18 C19 -0.1(3) . . . . ?
C17 C18 C19 C20 -0.3(2) . . . . ?
C18 C19 C20 C21 0.6(2) . . . . ?
C18 C19 C20 C22 -179.31(14) . . . . ?
C30 N3 C21 C20 -9.74(17) . . . . ?
C28 N3 C21 C20 -176.74(15) . . . . ?
C30 N3 C21 C16 172.22(15) . . . . ?
C28 N3 C21 C16 5.2(3) . . . . ?
C19 C20 C21 N3 -178.80(13) . . . . ?
C22 C20 C21 N3 1.16(15) . . . . ?
C19 C20 C21 C16 -0.6(2) . . . . ?
C22 C20 C21 C16 179.39(13) . . . . ?
C17 C16 C21 N3 178.00(16) . . . . ?
C17 C16 C21 C20 0.1(2) . . . . ?
C19 C20 C22 C29 63.39(19) . . . . ?
C21 C20 C22 C29 -116.56(13) . . . . ?
C19 C20 C22 C23 -62.34(17) . . . . ?
C21 C20 C22 C23 117.71(12) . . . . ?
C19 C20 C22 C30 -173.19(14) . . . . ?
C21 C20 C22 C30 6.86(14) . . . . ?
C20 C22 C23 O2 78.83(17) . . . . ?
C29 C22 C23 O2 -47.63(19) . . . . ?
C30 C22 C23 O2 -172.70(15) . . . . ?
C20 C22 C23 C24 -100.87(13) . . . . ?
C29 C22 C23 C24 132.67(13) . . . . ?
C30 C22 C23 C24 7.60(15) . . . . ?
C27 N4 C24 C25 0.74(17) . . . . ?
C30 N4 C24 C25 -179.70(12) . . . . ?
C27 N4 C24 C23 -176.93(12) . . . . ?
C30 N4 C24 C23 2.63(16) . . . . ?
O2 C23 C24 N4 173.89(16) . . . . ?
C22 C23 C24 N4 -6.44(16) . . . . ?
O2 C23 C24 C25 -2.4(3) . . . . ?
C22 C23 C24 C25 177.3(2) . . . . ?
N4 C24 C25 C26 -0.29(18) . . . . ?
C23 C24 C25 C26 176.0(2) . . . . ?
C24 C25 C26 C27 -0.3(2) . . . . ?
C24 N4 C27 C26 -0.91(18) . . . . ?
C30 N4 C27 C26 179.68(15) . . . . ?
C25 C26 C27 N4 0.7(2) . . . . ?
C21 N3 C30 N4 -98.19(14) . . . . ?
C28 N3 C30 N4 69.02(19) . . . . ?
C21 N3 C30 C22 13.81(16) . . . . ?
C28 N3 C30 C22 -178.99(15) . . . . ?
C27 N4 C30 N3 -64.4(2) . . . . ?
C24 N4 C30 N3 116.21(14) . . . . ?
C27 N4 C30 C22 -178.37(15) . . . . ?
C24 N4 C30 C22 2.24(15) . . . . ?
C20 C22 C30 N3 -12.09(14) . . . . ?
C29 C22 C30 N3 110.68(14) . . . . ?
C23 C22 C30 N3 -125.66(12) . . . . ?
C20 C22 C30 N4 107.77(11) . . . . ?
C29 C22 C30 N4 -129.46(13) . . . . ?
C23 C22 C30 N4 -5.80(13) . . . . ?

_diffrn_measured_fraction_theta_max 0.992
_diffrn_reflns_theta_full        68.42
_diffrn_measured_fraction_theta_full 0.992
_refine_diff_density_max         0.128
_refine_diff_density_min         -0.236
_refine_diff_density_rms         0.037
