# Electronic Supplementary Material (ESI) for Organic & Biomolecular Chemistry.
# This journal is © The Royal Society of Chemistry 2016

####################################################################### 
# 
# 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_compound9a
_database_code_depnum_ccdc_archive 'CCDC 1453189'
_audit_update_record             
;
2016-02-13 deposited with the CCDC.
2016-04-08 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C31 H22 N2 O2'
_chemical_formula_sum            'C31 H22 N2 O2'
_chemical_formula_weight         454.51

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           triclinic
_symmetry_space_group_name_H-M   P-1

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

_cell_length_a                   9.4276(5)
_cell_length_b                   11.2761(9)
_cell_length_c                   11.6981(10)
_cell_angle_alpha                112.674(8)
_cell_angle_beta                 90.151(5)
_cell_angle_gamma                96.976(5)
_cell_volume                     1137.32(14)
_cell_formula_units_Z            2
_cell_measurement_temperature    298(2)
_cell_measurement_reflns_used    2708
_cell_measurement_theta_min      4.1000
_cell_measurement_theta_max      71.8710

_exptl_crystal_description       needle
_exptl_crystal_colour            red
_exptl_crystal_size_max          0.36
_exptl_crystal_size_mid          0.24
_exptl_crystal_size_min          0.12
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.327
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             476
_exptl_absorpt_coefficient_mu    0.660
_exptl_absorpt_correction_type   empirical
_exptl_absorpt_correction_T_min  0.827
_exptl_absorpt_correction_T_max  0.924
_exptl_absorpt_process_details   'SADABS, SHELDRICK (1996)'

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      298(2)
_diffrn_radiation_wavelength     1.54184
_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            7843
_diffrn_reflns_av_R_equivalents  0.0220
_diffrn_reflns_av_sigmaI/netI    0.0333
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_theta_min         4.29
_diffrn_reflns_theta_max         71.73
_reflns_number_total             4333
_reflns_number_gt                3382
_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)+(0.0674P)²+0.0934P] 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         4333
_refine_ls_number_parameters     317
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0579
_refine_ls_R_factor_gt           0.0449
_refine_ls_wR_factor_ref         0.1290
_refine_ls_wR_factor_gt          0.1166
_refine_ls_goodness_of_fit_ref   1.029
_refine_ls_restrained_S_all      1.029
_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
N2 N 0.14879(14) 0.29952(12) 0.82227(12) 0.0427(3) Uani 1 1 d . . .
N1 N 0.40279(15) 0.31514(14) 1.05752(13) 0.0467(3) Uani 1 1 d . . .
O1 O 0.22540(14) 0.10562(11) 0.80706(13) 0.0589(3) Uani 1 1 d . . .
C8 C 0.30357(17) 0.31744(16) 0.97430(15) 0.0439(3) Uani 1 1 d . . .
C10 C 0.17711(16) 0.43232(14) 0.89812(14) 0.0397(3) Uani 1 1 d . . .
O2 O -0.24022(16) 0.30383(15) 0.47548(13) 0.0689(4) Uani 1 1 d . . .
C18 C 0.02618(16) 0.40485(15) 0.73614(14) 0.0416(3) Uani 1 1 d . . .
C7 C 0.27732(16) 0.44151(15) 0.99707(15) 0.0416(3) Uani 1 1 d . . .
C23 C 0.05548(17) 0.28106(15) 0.72244(14) 0.0426(3) Uani 1 1 d . . .
C1 C 0.36544(16) 0.52557(16) 1.10490(14) 0.0432(3) Uani 1 1 d . . .
C9 C 0.22614(17) 0.22145(15) 0.86062(15) 0.0441(4) Uani 1 1 d . . .
C12 C 0.11388(15) 0.64176(15) 0.89031(15) 0.0409(3) Uani 1 1 d . . .
C19 C -0.07300(17) 0.41678(17) 0.65375(15) 0.0471(4) Uani 1 1 d . . .
H19 H -0.0945 0.4978 0.6617 0.057 Uiso 1 1 calc R . .
C17 C 0.12034(17) 0.70110(16) 0.80518(17) 0.0479(4) Uani 1 1 d . . .
H17 H 0.1156 0.6502 0.7207 0.058 Uiso 1 1 calc R . .
C20 C -0.13868(18) 0.30495(18) 0.55982(15) 0.0514(4) Uani 1 1 d . . .
C11 C 0.10636(16) 0.50054(15) 0.84762(14) 0.0400(3) Uani 1 1 d . . .
C6 C 0.44168(17) 0.44224(17) 1.13936(15) 0.0462(4) Uani 1 1 d . . .
C13 C 0.11929(17) 0.71982(16) 1.01599(16) 0.0480(4) Uani 1 1 d . . .
H13 H 0.1138 0.6819 1.0740 0.058 Uiso 1 1 calc R . .
C25 C 0.39776(18) 0.17855(16) 1.18130(15) 0.0475(4) Uani 1 1 d . . .
C5 C 0.54139(19) 0.4877(2) 1.23938(16) 0.0545(4) Uani 1 1 d . . .
H5 H 0.5910 0.4313 1.2595 0.065 Uiso 1 1 calc R . .
C2 C 0.39234(19) 0.65922(18) 1.17645(16) 0.0520(4) Uani 1 1 d . . .
H2 H 0.3452 0.7171 1.1564 0.062 Uiso 1 1 calc R . .
C24 C 0.4508(2) 0.20150(18) 1.06812(17) 0.0529(4) Uani 1 1 d . . .
H24A H 0.5546 0.2121 1.0722 0.064 Uiso 1 1 calc R . .
H24B H 0.4174 0.1257 0.9942 0.064 Uiso 1 1 calc R . .
C15 C 0.14019(19) 0.91078(17) 0.9699(2) 0.0601(5) Uani 1 1 d . . .
H15 H 0.1496 1.0006 0.9965 0.072 Uiso 1 1 calc R . .
C22 C -0.00883(19) 0.16945(16) 0.62815(16) 0.0514(4) Uani 1 1 d . . .
H22 H 0.0123 0.0882 0.6200 0.062 Uiso 1 1 calc R . .
C16 C 0.13362(19) 0.83443(18) 0.8448(2) 0.0571(4) Uani 1 1 d . . .
H16 H 0.1381 0.8727 0.7871 0.069 Uiso 1 1 calc R . .
C21 C -0.1058(2) 0.18275(18) 0.54628(17) 0.0563(4) Uani 1 1 d . . .
H21 H -0.1498 0.1093 0.4813 0.068 Uiso 1 1 calc R . .
C14 C 0.13282(19) 0.85357(17) 1.05587(19) 0.0579(5) Uani 1 1 d . . .
H14 H 0.1369 0.9049 1.1402 0.070 Uiso 1 1 calc R . .
C30 C 0.4781(2) 0.1177(2) 1.2356(2) 0.0654(5) Uani 1 1 d . . .
H30 H 0.5657 0.0941 1.2049 0.079 Uiso 1 1 calc R . .
C4 C 0.5637(2) 0.6187(2) 1.30729(17) 0.0609(5) Uani 1 1 d . . .
H4 H 0.6295 0.6520 1.3750 0.073 Uiso 1 1 calc R . .
C26 C 0.2679(2) 0.2130(2) 1.22883(19) 0.0603(5) Uani 1 1 d . . .
H26 H 0.2128 0.2539 1.1930 0.072 Uiso 1 1 calc R . .
C3 C 0.4894(2) 0.7034(2) 1.27661(17) 0.0602(5) Uani 1 1 d . . .
H3 H 0.5059 0.7917 1.3252 0.072 Uiso 1 1 calc R . .
C29 C 0.4277(3) 0.0918(3) 1.3365(2) 0.0867(8) Uani 1 1 d . . .
H29 H 0.4822 0.0509 1.3728 0.104 Uiso 1 1 calc R . .
C31 C -0.2949(2) 0.4212(3) 0.4967(2) 0.0737(6) Uani 1 1 d . . .
H31A H -0.3216 0.4582 0.5812 0.111 Uiso 1 1 calc R . .
H31B H -0.3774 0.4046 0.4418 0.111 Uiso 1 1 calc R . .
H31C H -0.2230 0.4807 0.4817 0.111 Uiso 1 1 calc R . .
C28 C 0.2982(3) 0.1261(2) 1.3827(2) 0.0829(7) Uani 1 1 d . . .
H28 H 0.2646 0.1080 1.4497 0.099 Uiso 1 1 calc R . .
C27 C 0.2194(3) 0.1870(2) 1.3296(2) 0.0774(6) Uani 1 1 d . . .
H27 H 0.1323 0.2113 1.3613 0.093 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
N2 C23 1.394(2) . ?
N2 C9 1.402(2) . ?
N2 C10 1.4065(19) . ?
N1 C8 1.358(2) . ?
N1 C6 1.385(2) . ?
N1 C24 1.458(2) . ?
O1 C9 1.211(2) . ?
C8 C7 1.374(2) . ?
C8 C9 1.472(2) . ?
C10 C11 1.363(2) . ?
C10 C7 1.456(2) . ?
O2 C20 1.368(2) . ?
O2 C31 1.411(3) . ?
C18 C19 1.395(2) . ?
C18 C23 1.404(2) . ?
C18 C11 1.466(2) . ?
C7 C1 1.436(2) . ?
C23 C22 1.382(2) . ?
C1 C2 1.403(2) . ?
C1 C6 1.420(2) . ?
C12 C13 1.389(2) . ?
C12 C17 1.395(2) . ?
C12 C11 1.466(2) . ?
C19 C20 1.385(2) . ?
C17 C16 1.381(2) . ?
C20 C21 1.398(3) . ?
C6 C5 1.389(2) . ?
C13 C14 1.385(2) . ?
C25 C30 1.381(3) . ?
C25 C26 1.383(3) . ?
C25 C24 1.519(2) . ?
C5 C4 1.370(3) . ?
C2 C3 1.375(3) . ?
C15 C16 1.379(3) . ?
C15 C14 1.387(3) . ?
C22 C21 1.384(3) . ?
C30 C29 1.392(3) . ?
C4 C3 1.399(3) . ?
C26 C27 1.387(3) . ?
C29 C28 1.375(4) . ?
C28 C27 1.363(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
C23 N2 C9 136.35(14) . . ?
C23 N2 C10 109.92(13) . . ?
C9 N2 C10 113.59(13) . . ?
C8 N1 C6 106.83(14) . . ?
C8 N1 C24 127.49(15) . . ?
C6 N1 C24 125.44(15) . . ?
N1 C8 C7 111.73(15) . . ?
N1 C8 C9 135.71(15) . . ?
C7 C8 C9 112.34(14) . . ?
C11 C10 N2 109.05(14) . . ?
C11 C10 C7 145.19(15) . . ?
N2 C10 C7 105.66(13) . . ?
C20 O2 C31 117.39(16) . . ?
C19 C18 C23 119.50(15) . . ?
C19 C18 C11 132.05(15) . . ?
C23 C18 C11 108.31(14) . . ?
C8 C7 C1 106.69(14) . . ?
C8 C7 C10 106.63(14) . . ?
C1 C7 C10 146.57(15) . . ?
C22 C23 N2 131.42(15) . . ?
C22 C23 C18 122.22(16) . . ?
N2 C23 C18 106.26(14) . . ?
C2 C1 C6 117.88(15) . . ?
C2 C1 C7 136.95(16) . . ?
C6 C1 C7 105.17(14) . . ?
O1 C9 N2 125.80(16) . . ?
O1 C9 C8 132.48(16) . . ?
N2 C9 C8 101.71(13) . . ?
C13 C12 C17 118.47(15) . . ?
C13 C12 C11 121.02(15) . . ?
C17 C12 C11 120.48(15) . . ?
C20 C19 C18 118.40(16) . . ?
C16 C17 C12 120.84(17) . . ?
O2 C20 C19 123.84(18) . . ?
O2 C20 C21 114.95(16) . . ?
C19 C20 C21 121.20(16) . . ?
C10 C11 C18 106.43(13) . . ?
C10 C11 C12 127.64(14) . . ?
C18 C11 C12 125.84(14) . . ?
N1 C6 C5 127.58(17) . . ?
N1 C6 C1 109.57(14) . . ?
C5 C6 C1 122.83(17) . . ?
C14 C13 C12 120.72(17) . . ?
C30 C25 C26 118.97(18) . . ?
C30 C25 C24 119.56(17) . . ?
C26 C25 C24 121.43(16) . . ?
C4 C5 C6 117.42(18) . . ?
C3 C2 C1 119.01(18) . . ?
N1 C24 C25 113.16(14) . . ?
C16 C15 C14 119.93(16) . . ?
C23 C22 C21 117.69(16) . . ?
C15 C16 C17 120.07(18) . . ?
C22 C21 C20 120.98(16) . . ?
C13 C14 C15 119.95(17) . . ?
C25 C30 C29 120.0(2) . . ?
C5 C4 C3 121.20(18) . . ?
C25 C26 C27 120.4(2) . . ?
C2 C3 C4 121.65(19) . . ?
C28 C29 C30 120.6(2) . . ?
C27 C28 C29 119.4(2) . . ?
C28 C27 C26 120.7(2) . . ?

_diffrn_measured_fraction_theta_max 0.971
_diffrn_reflns_theta_full        71.73
_diffrn_measured_fraction_theta_full 0.971
_refine_diff_density_max         0.158
_refine_diff_density_min         -0.197
_refine_diff_density_rms         0.040
_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_compound10h
_database_code_depnum_ccdc_archive 'CCDC 1453190'
_audit_update_record             
;
2016-02-13 deposited with the CCDC.
2016-04-08 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C26 H22 N2 O2'
_chemical_formula_sum            'C26 H22 N2 O2'
_chemical_formula_weight         394.46

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 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           triclinic
_symmetry_space_group_name_H-M   P-1

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

_cell_length_a                   11.5059(4)
_cell_length_b                   12.8459(6)
_cell_length_c                   15.6020(8)
_cell_angle_alpha                106.081(4)
_cell_angle_beta                 93.226(4)
_cell_angle_gamma                109.728(4)
_cell_volume                     2056.95(16)
_cell_formula_units_Z            4
_cell_measurement_temperature    298(2)
_cell_measurement_reflns_used    5424
_cell_measurement_theta_min      4.1460
_cell_measurement_theta_max      71.9390

_exptl_crystal_description       block
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.18
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.07
_exptl_crystal_density_meas      none
_exptl_crystal_density_diffrn    1.274
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             858
_exptl_absorpt_coefficient_mu    0.643
_exptl_absorpt_correction_type   empirical
_exptl_absorpt_correction_T_min  0.71755
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_process_details   'SADABS, SHELDRICK (1996)'

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      298(2)
_diffrn_radiation_wavelength     1.54184
_diffrn_radiation_type           CuK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Xcalibur, Eos, Gemini'
_diffrn_measurement_method       'ω scans'
_diffrn_detector_area_resol_mean 16.3291
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            14639
_diffrn_reflns_av_R_equivalents  0.0214
_diffrn_reflns_av_sigmaI/netI    0.0290
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_theta_min         3.85
_diffrn_reflns_theta_max         72.00
_reflns_number_total             7879
_reflns_number_gt                6320
_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)+(0.0721P)²+0.2922P] 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         7879
_refine_ls_number_parameters     547
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0600
_refine_ls_R_factor_gt           0.0488
_refine_ls_wR_factor_ref         0.1402
_refine_ls_wR_factor_gt          0.1277
_refine_ls_goodness_of_fit_ref   1.034
_refine_ls_restrained_S_all      1.034
_refine_ls_shift/su_max          0.018
_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
O3 O 0.26230(13) 0.10445(13) 0.33572(8) 0.0633(3) Uani 1 1 d . . .
N4 N 0.21335(12) 0.14222(11) 0.47866(9) 0.0423(3) Uani 1 1 d . . .
C34 C 0.29775(13) -0.02113(13) 0.51263(11) 0.0430(3) Uani 1 1 d . . .
C37 C 0.26135(14) 0.08374(14) 0.40826(11) 0.0453(3) Uani 1 1 d . . .
N3 N 0.35624(13) -0.07003(13) 0.37539(10) 0.0499(3) Uani 1 1 d . . .
C36 C 0.20863(13) 0.12369(13) 0.56318(10) 0.0414(3) Uani 1 1 d . . .
C33 C 0.30537(14) 0.00098(14) 0.43084(11) 0.0440(3) Uani 1 1 d . . .
O4 O 0.01814(13) 0.44710(12) 0.38753(10) 0.0643(3) Uani 1 1 d . . .
C45 C 0.16373(14) 0.22425(13) 0.45880(10) 0.0413(3) Uani 1 1 d . . .
C32 C 0.38098(14) -0.13909(14) 0.42175(12) 0.0495(4) Uani 1 1 d . . .
C49 C 0.18546(15) 0.41997(14) 0.46998(11) 0.0466(3) Uani 1 1 d . . .
H49 H 0.2315 0.4996 0.4924 0.056 Uiso 1 1 calc R . .
C48 C 0.07073(15) 0.37835(15) 0.41446(11) 0.0467(3) Uani 1 1 d . . .
C35 C 0.24978(14) 0.04360(14) 0.58081(11) 0.0440(3) Uani 1 1 d . . .
H35 H 0.2467 0.0312 0.6367 0.053 Uiso 1 1 calc R . .
C38 C 0.15510(14) 0.19405(13) 0.63001(10) 0.0419(3) Uani 1 1 d . . .
C39 C 0.02679(15) 0.16449(14) 0.62411(11) 0.0487(4) Uani 1 1 d . . .
H39 H -0.0266 0.1004 0.5772 0.058 Uiso 1 1 calc R . .
C50 C 0.23132(14) 0.34188(14) 0.49200(11) 0.0452(3) Uani 1 1 d . . .
H50 H 0.3082 0.3694 0.5294 0.054 Uiso 1 1 calc R . .
C27 C 0.34542(14) -0.11187(14) 0.50764(12) 0.0468(4) Uani 1 1 d . . .
C46 C 0.04784(15) 0.18279(14) 0.40474(11) 0.0490(4) Uani 1 1 d . . .
H46 H 0.0015 0.1031 0.3831 0.059 Uiso 1 1 calc R . .
C47 C 0.00124(15) 0.25949(16) 0.38304(12) 0.0526(4) Uani 1 1 d . . .
H47 H -0.0770 0.2317 0.3473 0.063 Uiso 1 1 calc R . .
C40 C -0.02264(17) 0.22883(16) 0.68673(13) 0.0547(4) Uani 1 1 d . . .
H40 H -0.1091 0.2072 0.6816 0.066 Uiso 1 1 calc R . .
C43 C 0.23178(17) 0.28982(16) 0.70057(12) 0.0558(4) Uani 1 1 d . . .
H43 H 0.3182 0.3111 0.7062 0.067 Uiso 1 1 calc R . .
C41 C 0.05368(19) 0.32509(16) 0.75720(12) 0.0561(4) Uani 1 1 d . . .
C31 C 0.43443(16) -0.22319(16) 0.39432(15) 0.0602(5) Uani 1 1 d . . .
H31 H 0.4569 -0.2413 0.3373 0.072 Uiso 1 1 calc R . .
C28 C 0.36324(16) -0.17102(16) 0.56759(14) 0.0577(4) Uani 1 1 d . . .
H28 H 0.3391 -0.1555 0.6242 0.069 Uiso 1 1 calc R . .
C30 C 0.45237(18) -0.27796(17) 0.45500(18) 0.0690(6) Uani 1 1 d . . .
H30 H 0.4889 -0.3336 0.4389 0.083 Uiso 1 1 calc R . .
C42 C 0.18117(19) 0.35423(16) 0.76292(13) 0.0610(5) Uani 1 1 d . . .
H42 H 0.2344 0.4186 0.8097 0.073 Uiso 1 1 calc R . .
C29 C 0.41729(19) -0.25248(17) 0.54026(17) 0.0685(5) Uani 1 1 d . . .
H29 H 0.4309 -0.2916 0.5795 0.082 Uiso 1 1 calc R . .
C52 C 0.3862(2) -0.0709(2) 0.28635(14) 0.0694(5) Uani 1 1 d . . .
H52A H 0.4713 -0.0656 0.2851 0.104 Uiso 1 1 calc R . .
H52B H 0.3760 -0.0058 0.2727 0.104 Uiso 1 1 calc R . .
H52C H 0.3312 -0.1420 0.2422 0.104 Uiso 1 1 calc R . .
C51 C 0.0907(2) 0.56758(19) 0.41113(18) 0.0739(6) Uani 1 1 d . . .
H51A H 0.1170 0.5992 0.4755 0.111 Uiso 1 1 calc R . .
H51B H 0.0413 0.6068 0.3922 0.111 Uiso 1 1 calc R . .
H51C H 0.1629 0.5784 0.3817 0.111 Uiso 1 1 calc R . .
C44 C -0.0017(3) 0.3969(2) 0.82375(17) 0.0855(7) Uani 1 1 d . . .
H44A H -0.0135 0.4553 0.8009 0.128 Uiso 1 1 calc R . .
H44B H 0.0541 0.4337 0.8806 0.128 Uiso 1 1 calc R . .
H44C H -0.0810 0.3472 0.8321 0.128 Uiso 1 1 calc R . .
N2 N 0.72226(12) 0.13726(12) 0.09389(9) 0.0461(3) Uani 1 1 d . . .
N1 N 0.86015(14) -0.08505(12) 0.08764(9) 0.0512(3) Uani 1 1 d . . .
C7 C 0.79740(14) -0.02275(14) -0.02264(11) 0.0440(3) Uani 1 1 d . . .
O1 O 0.76429(14) 0.07585(12) 0.21264(8) 0.0647(3) Uani 1 1 d . . .
C11 C 0.80988(15) -0.00887(14) 0.06904(11) 0.0452(3) Uani 1 1 d . . .
C6 C 0.84217(14) -0.11323(14) -0.06351(11) 0.0458(3) Uani 1 1 d . . .
C9 C 0.71359(14) 0.12809(14) 0.00163(11) 0.0457(3) Uani 1 1 d . . .
O2 O 0.54269(14) 0.43853(12) 0.32773(11) 0.0735(4) Uani 1 1 d . . .
C10 C 0.76696(16) 0.06869(14) 0.13251(11) 0.0485(4) Uani 1 1 d . . .
C19 C 0.67406(15) 0.21472(14) 0.15346(11) 0.0472(3) Uani 1 1 d . . .
C22 C 0.58077(17) 0.36153(15) 0.26776(12) 0.0547(4) Uani 1 1 d . . .
C20 C 0.75529(16) 0.31282(15) 0.22030(12) 0.0514(4) Uani 1 1 d . . .
H20 H 0.8411 0.3293 0.2267 0.062 Uiso 1 1 calc R . .
C1 C 0.87990(15) -0.14930(14) 0.00728(11) 0.0487(4) Uani 1 1 d . . .
C12 C 0.66930(15) 0.21112(15) -0.02802(11) 0.0487(4) Uani 1 1 d . . .
C8 C 0.74865(15) 0.04880(15) -0.05633(11) 0.0479(4) Uani 1 1 d . . .
H8 H 0.7409 0.0412 -0.1176 0.057 Uiso 1 1 calc R . .
C5 C 0.85333(17) -0.16754(16) -0.15210(12) 0.0556(4) Uani 1 1 d . . .
H5 H 0.8294 -0.1449 -0.1998 0.067 Uiso 1 1 calc R . .
C21 C 0.70852(17) 0.38581(15) 0.27724(12) 0.0570(4) Uani 1 1 d . . .
H21 H 0.7628 0.4517 0.3223 0.068 Uiso 1 1 calc R . .
C3 C 0.93729(19) -0.28956(18) -0.09630(15) 0.0653(5) Uani 1 1 d . . .
H3 H 0.9683 -0.3493 -0.1087 0.078 Uiso 1 1 calc R . .
C2 C 0.92881(18) -0.23706(16) -0.00843(14) 0.0596(4) Uani 1 1 d . . .
H2 H 0.9548 -0.2594 0.0388 0.072 Uiso 1 1 calc R . .
C26 C 0.9047(2) -0.0860(2) 0.17646(14) 0.0758(6) Uani 1 1 d . . .
H26A H 0.8534 -0.1567 0.1862 0.114 Uiso 1 1 calc R . .
H26B H 0.9001 -0.0203 0.2221 0.114 Uiso 1 1 calc R . .
H26C H 0.9899 -0.0815 0.1797 0.114 Uiso 1 1 calc R . .
C23 C 0.49999(18) 0.26299(18) 0.20161(14) 0.0653(5) Uani 1 1 d . . .
H23 H 0.4141 0.2459 0.1952 0.078 Uiso 1 1 calc R . .
C13 C 0.55040(19) 0.1770(2) -0.07542(16) 0.0695(5) Uani 1 1 d . . .
H13 H 0.4952 0.1004 -0.0885 0.083 Uiso 1 1 calc R . .
C4 C 0.90036(19) -0.25505(18) -0.16713(14) 0.0649(5) Uani 1 1 d . . .
H4 H 0.9077 -0.2920 -0.2258 0.078 Uiso 1 1 calc R . .
C17 C 0.7482(2) 0.32479(19) -0.01169(17) 0.0728(6) Uani 1 1 d . . .
H17 H 0.8290 0.3502 0.0196 0.087 Uiso 1 1 calc R . .
C24 C 0.54782(17) 0.18996(17) 0.14501(14) 0.0618(5) Uani 1 1 d . . .
H24 H 0.4936 0.1232 0.1007 0.074 Uiso 1 1 calc R . .
C15 C 0.5911(2) 0.3687(2) -0.08657(15) 0.0735(6) Uani 1 1 d . . .
C14 C 0.5124(2) 0.2553(2) -0.10360(17) 0.0825(7) Uani 1 1 d . . .
H14 H 0.4317 0.2305 -0.1348 0.099 Uiso 1 1 calc R . .
C16 C 0.7097(2) 0.4019(2) -0.04077(19) 0.0851(7) Uani 1 1 d . . .
H16 H 0.7654 0.4781 -0.0291 0.102 Uiso 1 1 calc R . .
C25 C 0.4116(2) 0.4067(2) 0.3265(2) 0.0935(9) Uani 1 1 d . . .
H25A H 0.3732 0.4089 0.2711 0.140 Uiso 1 1 calc R . .
H25B H 0.3963 0.4603 0.3769 0.140 Uiso 1 1 calc R . .
H25C H 0.3769 0.3293 0.3306 0.140 Uiso 1 1 calc R . .
C18 C 0.5505(3) 0.4544(3) -0.1186(2) 0.1147(11) Uani 1 1 d . . .
H18A H 0.6034 0.5326 -0.0837 0.172 Uiso 1 1 calc R . .
H18B H 0.4652 0.4424 -0.1109 0.172 Uiso 1 1 calc R . .
H18C H 0.5572 0.4425 -0.1813 0.172 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 C37 1.232(2) . ?
N4 C37 1.402(2) . ?
N4 C36 1.4041(19) . ?
N4 C45 1.4490(18) . ?
C34 C33 1.383(2) . ?
C34 C35 1.419(2) . ?
C34 C27 1.432(2) . ?
C37 C33 1.436(2) . ?
N3 C32 1.376(2) . ?
N3 C33 1.380(2) . ?
N3 C52 1.448(2) . ?
C36 C35 1.352(2) . ?
C36 C38 1.486(2) . ?
O4 C48 1.3640(19) . ?
O4 C51 1.416(3) . ?
C45 C50 1.373(2) . ?
C45 C46 1.385(2) . ?
C32 C31 1.397(2) . ?
C32 C27 1.409(2) . ?
C49 C48 1.385(2) . ?
C49 C50 1.390(2) . ?
C48 C47 1.388(2) . ?
C38 C43 1.383(2) . ?
C38 C39 1.385(2) . ?
C39 C40 1.376(2) . ?
C27 C28 1.404(2) . ?
C46 C47 1.376(2) . ?
C40 C41 1.383(3) . ?
C43 C42 1.383(3) . ?
C41 C42 1.377(3) . ?
C41 C44 1.508(3) . ?
C31 C30 1.371(3) . ?
C28 C29 1.373(3) . ?
C30 C29 1.396(3) . ?
N2 C10 1.403(2) . ?
N2 C9 1.406(2) . ?
N2 C19 1.442(2) . ?
N1 C1 1.375(2) . ?
N1 C11 1.377(2) . ?
N1 C26 1.455(2) . ?
C7 C11 1.385(2) . ?
C7 C8 1.421(2) . ?
C7 C6 1.433(2) . ?
O1 C10 1.231(2) . ?
C11 C10 1.434(2) . ?
C6 C5 1.400(2) . ?
C6 C1 1.410(2) . ?
C9 C8 1.351(2) . ?
C9 C12 1.492(2) . ?
O2 C22 1.368(2) . ?
O2 C25 1.420(3) . ?
C19 C24 1.368(2) . ?
C19 C20 1.384(2) . ?
C22 C23 1.380(3) . ?
C22 C21 1.386(3) . ?
C20 C21 1.375(2) . ?
C1 C2 1.392(2) . ?
C12 C17 1.376(3) . ?
C12 C13 1.383(2) . ?
C5 C4 1.375(3) . ?
C3 C2 1.375(3) . ?
C3 C4 1.394(3) . ?
C23 C24 1.381(3) . ?
C13 C14 1.385(3) . ?
C17 C16 1.381(3) . ?
C15 C14 1.370(4) . ?
C15 C16 1.373(3) . ?
C15 C18 1.519(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
C37 N4 C36 124.35(13) . . ?
C37 N4 C45 115.58(12) . . ?
C36 N4 C45 120.06(12) . . ?
C33 C34 C35 119.82(14) . . ?
C33 C34 C27 106.66(14) . . ?
C35 C34 C27 133.52(15) . . ?
O3 C37 N4 120.76(14) . . ?
O3 C37 C33 126.19(15) . . ?
N4 C37 C33 113.05(13) . . ?
C32 N3 C33 107.57(14) . . ?
C32 N3 C52 124.28(15) . . ?
C33 N3 C52 128.07(15) . . ?
C35 C36 N4 120.40(14) . . ?
C35 C36 C38 122.59(14) . . ?
N4 C36 C38 117.01(13) . . ?
N3 C33 C34 110.20(14) . . ?
N3 C33 C37 126.38(15) . . ?
C34 C33 C37 123.39(14) . . ?
C48 O4 C51 117.66(15) . . ?
C50 C45 C46 120.11(14) . . ?
C50 C45 N4 120.55(13) . . ?
C46 C45 N4 119.34(14) . . ?
N3 C32 C31 128.82(18) . . ?
N3 C32 C27 109.31(14) . . ?
C31 C32 C27 121.86(17) . . ?
C48 C49 C50 119.52(15) . . ?
O4 C48 C49 124.28(16) . . ?
O4 C48 C47 115.84(14) . . ?
C49 C48 C47 119.87(14) . . ?
C36 C35 C34 118.94(14) . . ?
C43 C38 C39 118.08(15) . . ?
C43 C38 C36 121.00(14) . . ?
C39 C38 C36 120.91(14) . . ?
C40 C39 C38 120.83(16) . . ?
C45 C50 C49 120.34(14) . . ?
C28 C27 C32 119.44(16) . . ?
C28 C27 C34 134.29(17) . . ?
C32 C27 C34 106.26(14) . . ?
C47 C46 C45 119.97(15) . . ?
C46 C47 C48 120.14(15) . . ?
C39 C40 C41 121.33(17) . . ?
C38 C43 C42 120.64(17) . . ?
C42 C41 C40 117.72(16) . . ?
C42 C41 C44 121.53(19) . . ?
C40 C41 C44 120.74(19) . . ?
C30 C31 C32 117.2(2) . . ?
C29 C28 C27 118.1(2) . . ?
C31 C30 C29 121.74(18) . . ?
C41 C42 C43 121.40(17) . . ?
C28 C29 C30 121.60(19) . . ?
C10 N2 C9 124.25(13) . . ?
C10 N2 C19 115.99(13) . . ?
C9 N2 C19 119.58(13) . . ?
C1 N1 C11 107.68(13) . . ?
C1 N1 C26 124.63(15) . . ?
C11 N1 C26 126.96(15) . . ?
C11 C7 C8 119.48(15) . . ?
C11 C7 C6 106.52(14) . . ?
C8 C7 C6 133.99(15) . . ?
N1 C11 C7 110.28(14) . . ?
N1 C11 C10 126.19(15) . . ?
C7 C11 C10 123.38(15) . . ?
C5 C6 C1 119.21(16) . . ?
C5 C6 C7 134.51(16) . . ?
C1 C6 C7 106.27(14) . . ?
C8 C9 N2 120.18(15) . . ?
C8 C9 C12 122.15(15) . . ?
N2 C9 C12 117.63(14) . . ?
C22 O2 C25 116.63(17) . . ?
O1 C10 N2 120.86(15) . . ?
O1 C10 C11 125.95(16) . . ?
N2 C10 C11 113.16(14) . . ?
C24 C19 C20 120.02(16) . . ?
C24 C19 N2 119.95(15) . . ?
C20 C19 N2 120.02(14) . . ?
O2 C22 C23 123.89(17) . . ?
O2 C22 C21 116.20(16) . . ?
C23 C22 C21 119.91(16) . . ?
C21 C20 C19 119.66(16) . . ?
N1 C1 C2 128.99(16) . . ?
N1 C1 C6 109.25(14) . . ?
C2 C1 C6 121.76(17) . . ?
C17 C12 C13 117.34(17) . . ?
C17 C12 C9 120.59(15) . . ?
C13 C12 C9 122.03(17) . . ?
C9 C8 C7 119.31(15) . . ?
C4 C5 C6 118.63(18) . . ?
C20 C21 C22 120.25(16) . . ?
C2 C3 C4 121.38(18) . . ?
C3 C2 C1 117.62(18) . . ?
C22 C23 C24 119.41(17) . . ?
C12 C13 C14 120.8(2) . . ?
C5 C4 C3 121.39(18) . . ?
C12 C17 C16 121.32(19) . . ?
C19 C24 C23 120.74(17) . . ?
C14 C15 C16 117.5(2) . . ?
C14 C15 C18 121.7(2) . . ?
C16 C15 C18 120.7(3) . . ?
C15 C14 C13 121.5(2) . . ?
C15 C16 C17 121.4(2) . . ?

_diffrn_measured_fraction_theta_max 0.974
_diffrn_reflns_theta_full        72.00
_diffrn_measured_fraction_theta_full 0.974
_refine_diff_density_max         0.193
_refine_diff_density_min         -0.260
_refine_diff_density_rms         0.064

_exptl_crystal_recrystallization_method 'Re-crystallisation from solvent: '
