# Electronic Supplementary Material (ESI) for Organic & Biomolecular Chemistry.
# This journal is © The Royal Society of Chemistry 2015

####################################################################### 
# 
# 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_ar22411b
_database_code_depnum_ccdc_archive 'CCDC 1036521'
_audit_update_record             
;
2014-11-27 deposited with the CCDC.
2015-01-06 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
'Ethyl 7-Methylene-6-oxo-6,7-dihydrobenzo[2,3]azepino[4,5-b]indole-12(5H)-carboxylate'
_chemical_name_common            ?
_chemical_melting_point          478
_chemical_formula_moiety         ?
_chemical_formula_sum            'C20 H16 N2 O3'
_chemical_formula_weight         332.35

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

_symmetry_cell_setting           Monoclinic
_symmetry_space_group_name_H-M   P2(1)/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                   9.2474(15)
_cell_length_b                   21.492(3)
_cell_length_c                   8.1455(13)
_cell_angle_alpha                90.00
_cell_angle_beta                 93.323(3)
_cell_angle_gamma                90.00
_cell_volume                     1616.2(4)
_cell_formula_units_Z            4
_cell_measurement_temperature    293
_cell_measurement_reflns_used    5485
_cell_measurement_theta_min      2.40
_cell_measurement_theta_max      24.93

_exptl_crystal_description       prism
_exptl_crystal_colour            'pale yellow'
_exptl_crystal_size_max          0.49
_exptl_crystal_size_mid          0.48
_exptl_crystal_size_min          0.23
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.366
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             696
_exptl_absorpt_coefficient_mu    0.093
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.6754
_exptl_absorpt_correction_T_max  0.7452
_exptl_absorpt_process_details   'SADABS V 2008/1, Sheldrick, G. M. (2008)'

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      293
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Bruker SMART 1000 CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            12062
_diffrn_reflns_av_R_equivalents  0.0223
_diffrn_reflns_av_sigmaI/netI    0.0179
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -25
_diffrn_reflns_limit_k_max       25
_diffrn_reflns_limit_l_min       -9
_diffrn_reflns_limit_l_max       9
_diffrn_reflns_theta_min         1.90
_diffrn_reflns_theta_max         25.07
_reflns_number_total             2852
_reflns_number_gt                2361
_reflns_threshold_expression     >2sigma(I)

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

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

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0443P)²+0.4868P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   'geom & difmap'
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         2852
_refine_ls_number_parameters     231
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0444
_refine_ls_R_factor_gt           0.0339
_refine_ls_wR_factor_ref         0.0959
_refine_ls_wR_factor_gt          0.0859
_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
N1 N 0.90593(13) 0.44671(6) 0.13577(17) 0.0399(3) Uani 1 1 d . . .
H1 H 0.8979(18) 0.4706(8) 0.047(2) 0.047(5) Uiso 1 1 d . . .
C2 C 1.03709(16) 0.44868(7) 0.21743(19) 0.0398(3) Uani 1 1 d . . .
C3 C 1.05945(16) 0.41236(7) 0.37330(19) 0.0405(4) Uani 1 1 d . . .
C4 C 1.1338(2) 0.43783(9) 0.4997(2) 0.0609(5) Uani 1 1 d . . .
H4A H 1.1581 0.4142 0.5929 0.073 Uiso 1 1 calc R . .
H4B H 1.1617 0.4793 0.4953 0.073 Uiso 1 1 calc R . .
N5 N 0.87785(12) 0.26094(5) 0.31165(15) 0.0364(3) Uani 1 1 d . . .
C6 C 0.87962(15) 0.32650(6) 0.30105(17) 0.0341(3) Uani 1 1 d . . .
C7 C 1.00989(15) 0.34742(7) 0.36694(17) 0.0364(3) Uani 1 1 d . . .
C7B C 1.09475(16) 0.29432(7) 0.42160(18) 0.0385(3) Uani 1 1 d . . .
C8 C 1.23524(17) 0.28821(8) 0.4935(2) 0.0482(4) Uani 1 1 d . . .
H8 H 1.2910 0.3233 0.5187 0.058 Uiso 1 1 calc R . .
C9 C 1.28959(19) 0.22994(8) 0.5262(2) 0.0573(5) Uani 1 1 d . . .
H9 H 1.3828 0.2254 0.5739 0.069 Uiso 1 1 calc R . .
C10 C 1.20617(19) 0.17748(8) 0.4883(2) 0.0582(5) Uani 1 1 d . . .
H10 H 1.2453 0.1384 0.5111 0.070 Uiso 1 1 calc R . .
C11 C 1.06747(18) 0.18164(8) 0.4182(2) 0.0502(4) Uani 1 1 d . . .
H11 H 1.0128 0.1462 0.3933 0.060 Uiso 1 1 calc R . .
C11B C 1.01196(15) 0.24112(7) 0.38600(18) 0.0383(3) Uani 1 1 d . . .
C12 C 0.77161(15) 0.42473(7) 0.18972(17) 0.0356(3) Uani 1 1 d . . .
C13 C 0.75307(15) 0.36571(6) 0.25798(17) 0.0339(3) Uani 1 1 d . . .
C14 C 0.61263(15) 0.34913(7) 0.29866(18) 0.0391(3) Uani 1 1 d . . .
H14 H 0.5974 0.3104 0.3455 0.047 Uiso 1 1 calc R . .
C15 C 0.49687(16) 0.38895(8) 0.27073(19) 0.0455(4) Uani 1 1 d . . .
H15 H 0.4048 0.3767 0.2978 0.055 Uiso 1 1 calc R . .
C16 C 0.51703(16) 0.44690(8) 0.2028(2) 0.0486(4) Uani 1 1 d . . .
H16 H 0.4390 0.4738 0.1844 0.058 Uiso 1 1 calc R . .
C17 C 0.65369(16) 0.46461(7) 0.1624(2) 0.0446(4) Uani 1 1 d . . .
H17 H 0.6675 0.5036 0.1165 0.054 Uiso 1 1 calc R . .
C18 C 0.77386(16) 0.22255(7) 0.23176(18) 0.0389(3) Uani 1 1 d . . .
O19 O 0.78112(12) 0.16577(5) 0.29631(14) 0.0508(3) Uani 1 1 d . . .
C20 C 0.6830(2) 0.11958(8) 0.2226(2) 0.0571(5) Uani 1 1 d . . .
H20A H 0.7183 0.0783 0.2512 0.068 Uiso 1 1 calc R . .
H20B H 0.6799 0.1236 0.1038 0.068 Uiso 1 1 calc R . .
C21 C 0.5346(2) 0.12760(10) 0.2808(3) 0.0792(7) Uani 1 1 d . . .
H21A H 0.5381 0.1250 0.3986 0.119 Uiso 1 1 calc R . .
H21B H 0.4726 0.0954 0.2349 0.119 Uiso 1 1 calc R . .
H21C H 0.4973 0.1675 0.2465 0.119 Uiso 1 1 calc R . .
O22 O 0.69198(12) 0.23940(5) 0.12173(13) 0.0491(3) Uani 1 1 d . . .
O23 O 1.13678(12) 0.47902(5) 0.16179(15) 0.0543(3) Uani 1 1 d . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
N1 C2 1.3497(19) . ?
N1 C12 1.4221(18) . ?
C2 O23 1.2365(18) . ?
C2 C3 1.495(2) . ?
C3 C4 1.323(2) . ?
C3 C7 1.469(2) . ?
N5 C18 1.3987(19) . ?
N5 C6 1.4117(18) . ?
N5 C11B 1.4139(18) . ?
C6 C7 1.3662(19) . ?
C6 C13 1.4681(19) . ?
C7 C7B 1.441(2) . ?
C7B C11B 1.397(2) . ?
C7B C8 1.400(2) . ?
C8 C9 1.370(2) . ?
C9 C10 1.391(3) . ?
C10 C11 1.376(2) . ?
C11 C11B 1.397(2) . ?
C12 C17 1.395(2) . ?
C12 C13 1.400(2) . ?
C13 C14 1.405(2) . ?
C14 C15 1.379(2) . ?
C15 C16 1.380(2) . ?
C16 C17 1.378(2) . ?
C18 O22 1.1954(18) . ?
C18 O19 1.3290(18) . ?
O19 C20 1.4512(19) . ?
C20 C21 1.488(3) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C2 N1 C12 129.36(13) . . ?
O23 C2 N1 120.25(14) . . ?
O23 C2 C3 121.16(13) . . ?
N1 C2 C3 118.58(13) . . ?
C4 C3 C7 124.58(15) . . ?
C4 C3 C2 119.01(15) . . ?
C7 C3 C2 116.03(12) . . ?
C18 N5 C6 124.77(12) . . ?
C18 N5 C11B 125.72(12) . . ?
C6 N5 C11B 108.30(11) . . ?
C7 C6 N5 108.51(12) . . ?
C7 C6 C13 125.27(13) . . ?
N5 C6 C13 125.15(12) . . ?
C6 C7 C7B 108.23(13) . . ?
C6 C7 C3 126.35(13) . . ?
C7B C7 C3 125.34(13) . . ?
C11B C7B C8 119.61(14) . . ?
C11B C7B C7 107.58(12) . . ?
C8 C7B C7 132.78(14) . . ?
C9 C8 C7B 119.22(16) . . ?
C8 C9 C10 120.37(16) . . ?
C11 C10 C9 122.08(16) . . ?
C10 C11 C11B 117.44(16) . . ?
C11 C11B C7B 121.27(14) . . ?
C11 C11B N5 131.30(14) . . ?
C7B C11B N5 107.38(12) . . ?
C17 C12 C13 120.51(13) . . ?
C17 C12 N1 115.82(13) . . ?
C13 C12 N1 123.58(13) . . ?
C12 C13 C14 117.38(13) . . ?
C12 C13 C6 120.06(12) . . ?
C14 C13 C6 122.21(13) . . ?
C15 C14 C13 121.54(14) . . ?
C14 C15 C16 120.31(14) . . ?
C17 C16 C15 119.48(14) . . ?
C16 C17 C12 120.79(14) . . ?
O22 C18 O19 126.15(14) . . ?
O22 C18 N5 123.97(13) . . ?
O19 C18 N5 109.88(12) . . ?
C18 O19 C20 116.64(12) . . ?
O19 C20 C21 110.80(16) . . ?

_diffrn_measured_fraction_theta_max 0.994
_diffrn_reflns_theta_full        25.00
_diffrn_measured_fraction_theta_full 0.999
_refine_diff_density_max         0.171
_refine_diff_density_min         -0.173
_refine_diff_density_rms         0.032
_exptl_crystal_recrystallization_method 'Re-crystallisation from solvent: '
####################################################################### 
# 
# 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_ar22412s
_database_code_depnum_ccdc_archive 'CCDC 1036522'
_audit_update_record             
;
2014-11-27 deposited with the CCDC.
2015-01-06 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
'(Z)-Ethyl 7-(2-Ethoxy-2-oxoethylene)-6-oxo-6,7-dihydrobenzo[2,3]azepino[4,5-b]indole-12(5H)-carboxylate '
_chemical_name_common            ?
_chemical_melting_point          473
_chemical_formula_moiety         ?
_chemical_formula_sum            'C23 H20 N2 O5'
_chemical_formula_weight         404.41

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

_symmetry_cell_setting           Monoclinic
_symmetry_space_group_name_H-M   P2(1)/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                   10.7866(18)
_cell_length_b                   14.366(2)
_cell_length_c                   13.573(2)
_cell_angle_alpha                90.00
_cell_angle_beta                 111.734(3)
_cell_angle_gamma                90.00
_cell_volume                     1953.7(6)
_cell_formula_units_Z            4
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    3792
_cell_measurement_theta_min      2.48
_cell_measurement_theta_max      24.92

_exptl_crystal_description       prism
_exptl_crystal_colour            'pale yellow'
_exptl_crystal_size_max          0.52
_exptl_crystal_size_mid          0.38
_exptl_crystal_size_min          0.20
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.375
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             848
_exptl_absorpt_coefficient_mu    0.098
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.7142
_exptl_absorpt_correction_T_max  0.7452
_exptl_absorpt_process_details   'SADABS V. 2008/1, Sheldrick, G. M. (2008)'

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Bruker SMART 1000 CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            14633
_diffrn_reflns_av_R_equivalents  0.0305
_diffrn_reflns_av_sigmaI/netI    0.0263
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_theta_min         2.03
_diffrn_reflns_theta_max         25.02
_reflns_number_total             3447
_reflns_number_gt                2379
_reflns_threshold_expression     >2sigma(I)

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

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

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0370P)²+0.9451P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   'geom & difmap'
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         3447
_refine_ls_number_parameters     277
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0676
_refine_ls_R_factor_gt           0.0376
_refine_ls_wR_factor_ref         0.1058
_refine_ls_wR_factor_gt          0.0853
_refine_ls_goodness_of_fit_ref   1.021
_refine_ls_restrained_S_all      1.021
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
N1 N 0.45811(17) 0.01707(13) 0.83461(14) 0.0463(4) Uani 1 1 d . . .
H1 H 0.520(2) -0.0215(17) 0.8731(18) 0.062(7) Uiso 1 1 d . . .
C2 C 0.3459(2) 0.01514(15) 0.85840(16) 0.0432(5) Uani 1 1 d . . .
O3 O 0.32824(15) -0.04704(11) 0.91282(13) 0.0599(4) Uani 1 1 d . . .
C4 C 0.24296(19) 0.08888(14) 0.81065(16) 0.0410(5) Uani 1 1 d . . .
C5 C 0.1796(2) 0.13243(15) 0.86549(16) 0.0459(5) Uani 1 1 d . . .
H5 H 0.1119 0.1734 0.8277 0.055 Uiso 1 1 calc R . .
C6 C 0.2058(2) 0.12232(14) 0.97958(17) 0.0447(5) Uani 1 1 d . . .
O7 O 0.31253(15) 0.11042(12) 1.04965(12) 0.0613(4) Uani 1 1 d . . .
O8 O 0.09249(14) 0.13170(12) 0.99601(11) 0.0579(4) Uani 1 1 d . . .
C9 C 0.1000(2) 0.1269(2) 1.10484(17) 0.0641(7) Uani 1 1 d . . .
H9A H 0.1528 0.1782 1.1457 0.077 Uiso 1 1 calc R . .
H9B H 0.1417 0.0690 1.1373 0.077 Uiso 1 1 calc R . .
C10 C -0.0368(3) 0.1320(2) 1.1030(2) 0.0801(9) Uani 1 1 d . . .
H10A H -0.0776 0.1890 1.0696 0.120 Uiso 1 1 calc R . .
H10B H -0.0347 0.1303 1.1743 0.120 Uiso 1 1 calc R . .
H10C H -0.0875 0.0802 1.0639 0.120 Uiso 1 1 calc R . .
N11 N 0.20612(15) 0.12828(12) 0.53349(12) 0.0419(4) Uani 1 1 d . . .
C12 C 0.28520(19) 0.11478(14) 0.64237(15) 0.0396(5) Uani 1 1 d . . .
C13 C 0.20151(19) 0.10192(14) 0.69585(16) 0.0412(5) Uani 1 1 d . . .
C13B C 0.06505(19) 0.10712(14) 0.62154(16) 0.0433(5) Uani 1 1 d . . .
C14 C -0.0581(2) 0.09723(15) 0.63232(18) 0.0511(6) Uani 1 1 d . . .
H14 H -0.0627 0.0853 0.6982 0.061 Uiso 1 1 calc R . .
C15 C -0.1724(2) 0.10548(16) 0.5434(2) 0.0574(6) Uani 1 1 d . . .
H15 H -0.2552 0.1004 0.5495 0.069 Uiso 1 1 calc R . .
C16 C -0.1659(2) 0.12122(16) 0.44455(19) 0.0573(6) Uani 1 1 d . . .
H16 H -0.2447 0.1256 0.3855 0.069 Uiso 1 1 calc R . .
C17 C -0.0454(2) 0.13062(16) 0.43157(18) 0.0525(6) Uani 1 1 d . . .
H17 H -0.0416 0.1411 0.3651 0.063 Uiso 1 1 calc R . .
C17B C 0.06952(19) 0.12384(14) 0.52155(17) 0.0441(5) Uani 1 1 d . . .
C18 C 0.50699(19) 0.08712(14) 0.78507(15) 0.0409(5) Uani 1 1 d . . .
C19 C 0.42870(19) 0.13168(13) 0.69041(15) 0.0390(5) Uani 1 1 d . . .
C20 C 0.4912(2) 0.19804(15) 0.64855(17) 0.0471(5) Uani 1 1 d . . .
H20 H 0.4403 0.2305 0.5877 0.056 Uiso 1 1 calc R . .
C21 C 0.6257(2) 0.21635(16) 0.69504(19) 0.0555(6) Uani 1 1 d . . .
H21 H 0.6652 0.2599 0.6651 0.067 Uiso 1 1 calc R . .
C22 C 0.7018(2) 0.16954(18) 0.7865(2) 0.0589(6) Uani 1 1 d . . .
H22 H 0.7932 0.1805 0.8174 0.071 Uiso 1 1 calc R . .
C23 C 0.6425(2) 0.10679(16) 0.83176(17) 0.0512(6) Uani 1 1 d . . .
H23 H 0.6938 0.0771 0.8945 0.061 Uiso 1 1 calc R . .
C24 C 0.2421(2) 0.11970(15) 0.44467(16) 0.0440(5) Uani 1 1 d . . .
O25 O 0.16971(15) 0.14293(12) 0.35774(12) 0.0611(4) Uani 1 1 d . . .
O26 O 0.36156(14) 0.08186(10) 0.46910(10) 0.0478(4) Uani 1 1 d . . .
C27 C 0.4089(3) 0.07510(19) 0.38143(18) 0.0638(7) Uani 1 1 d . . .
H27A H 0.3368 0.0530 0.3186 0.077 Uiso 1 1 calc R . .
H27B H 0.4808 0.0300 0.3993 0.077 Uiso 1 1 calc R . .
C28 C 0.4572(3) 0.1661(2) 0.3579(2) 0.0902(10) Uani 1 1 d . . .
H28A H 0.3842 0.2094 0.3342 0.135 Uiso 1 1 calc R . .
H28B H 0.4931 0.1581 0.3035 0.135 Uiso 1 1 calc R . .
H28C H 0.5254 0.1897 0.4209 0.135 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 C2 1.364(2) . ?
N1 C18 1.416(3) . ?
C2 O3 1.218(2) . ?
C2 C4 1.497(3) . ?
C4 C5 1.337(3) . ?
C4 C13 1.465(3) . ?
C5 C6 1.475(3) . ?
C6 O7 1.203(2) . ?
C6 O8 1.328(2) . ?
O8 C9 1.451(2) . ?
C9 C10 1.468(3) . ?
N11 C24 1.402(3) . ?
N11 C12 1.420(2) . ?
N11 C17B 1.423(2) . ?
C12 C13 1.364(3) . ?
C12 C19 1.460(3) . ?
C13 C13B 1.446(3) . ?
C13B C17B 1.397(3) . ?
C13B C14 1.397(3) . ?
C14 C15 1.374(3) . ?
C15 C16 1.387(3) . ?
C16 C17 1.381(3) . ?
C17 C17B 1.384(3) . ?
C18 C23 1.390(3) . ?
C18 C19 1.404(3) . ?
C19 C20 1.403(3) . ?
C20 C21 1.377(3) . ?
C21 C22 1.383(3) . ?
C22 C23 1.375(3) . ?
C24 O25 1.196(2) . ?
C24 O26 1.322(2) . ?
O26 C27 1.462(2) . ?
C27 C28 1.485(4) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C2 N1 C18 130.25(18) . . ?
O3 C2 N1 120.68(19) . . ?
O3 C2 C4 121.59(18) . . ?
N1 C2 C4 117.65(18) . . ?
C5 C4 C13 120.96(18) . . ?
C5 C4 C2 122.67(18) . . ?
C13 C4 C2 115.85(17) . . ?
C4 C5 C6 126.84(19) . . ?
O7 C6 O8 123.51(19) . . ?
O7 C6 C5 126.83(19) . . ?
O8 C6 C5 109.62(17) . . ?
C6 O8 C9 117.28(17) . . ?
O8 C9 C10 107.67(19) . . ?
C24 N11 C12 129.20(16) . . ?
C24 N11 C17B 120.19(16) . . ?
C12 N11 C17B 108.07(15) . . ?
C13 C12 N11 108.15(17) . . ?
C13 C12 C19 125.86(18) . . ?
N11 C12 C19 124.82(17) . . ?
C12 C13 C13B 108.97(17) . . ?
C12 C13 C4 125.57(18) . . ?
C13B C13 C4 125.41(17) . . ?
C17B C13B C14 119.72(19) . . ?
C17B C13B C13 107.12(17) . . ?
C14 C13B C13 133.15(19) . . ?
C15 C14 C13B 118.5(2) . . ?
C14 C15 C16 120.9(2) . . ?
C17 C16 C15 121.7(2) . . ?
C16 C17 C17B 117.3(2) . . ?
C17 C17B C13B 121.85(19) . . ?
C17 C17B N11 130.43(19) . . ?
C13B C17B N11 107.69(17) . . ?
C23 C18 C19 119.95(19) . . ?
C23 C18 N1 116.21(19) . . ?
C19 C18 N1 123.72(18) . . ?
C20 C19 C18 117.64(18) . . ?
C20 C19 C12 121.38(18) . . ?
C18 C19 C12 120.79(17) . . ?
C21 C20 C19 121.8(2) . . ?
C20 C21 C22 119.6(2) . . ?
C23 C22 C21 120.0(2) . . ?
C22 C23 C18 121.0(2) . . ?
O25 C24 O26 125.57(19) . . ?
O25 C24 N11 122.40(19) . . ?
O26 C24 N11 112.01(17) . . ?
C24 O26 C27 115.14(16) . . ?
O26 C27 C28 111.9(2) . . ?

_diffrn_measured_fraction_theta_max 0.998
_diffrn_reflns_theta_full        25.00
_diffrn_measured_fraction_theta_full 0.999
_refine_diff_density_max         0.272
_refine_diff_density_min         -0.181
_refine_diff_density_rms         0.035
_exptl_crystal_recrystallization_method 'Re-crystallisation from solvent: '
