# Electronic Supplementary Material (ESI) for Chemical Communications
# This journal is © The Royal Society of Chemistry 2013

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#
#                 Cambridge Crystallographic Data Centre
#                                CCDC 
# 
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# 
#  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.
#
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#  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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#  data retrieval see:
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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_z

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

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

_symmetry_cell_setting           Monoclinic
_symmetry_space_group_name_H-M   P2(1)/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                   10.0938(5)
_cell_length_b                   19.9876(10)
_cell_length_c                   11.2239(6)
_cell_angle_alpha                90.00
_cell_angle_beta                 115.150(2)
_cell_angle_gamma                90.00
_cell_volume                     2049.76(18)
_cell_formula_units_Z            4
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    ?
_cell_measurement_theta_min      ?
_cell_measurement_theta_max      ?

_exptl_crystal_description       block
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.24
_exptl_crystal_size_mid          0.19
_exptl_crystal_size_min          0.12
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.256
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             824
_exptl_absorpt_coefficient_mu    0.082
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.9806
_exptl_absorpt_correction_T_max  0.9902
_exptl_absorpt_process_details   ?

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      296(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  ?
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            23363
_diffrn_reflns_av_R_equivalents  0.0477
_diffrn_reflns_av_sigmaI/netI    0.0305
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_k_min       -23
_diffrn_reflns_limit_k_max       23
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_theta_min         2.23
_diffrn_reflns_theta_max         25.01
_reflns_number_total             3577
_reflns_number_gt                2449
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_molecular_graphics    ?
_computing_publication_material  ?

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

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[\s^2^(Fo^2^)+(0.1017P)^2^+1.3324P] where P=(Fo^2^+2Fc^2^)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         3577
_refine_ls_number_parameters     262
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0930
_refine_ls_R_factor_gt           0.0639
_refine_ls_wR_factor_ref         0.2001
_refine_ls_wR_factor_gt          0.1741
_refine_ls_goodness_of_fit_ref   1.022
_refine_ls_restrained_S_all      1.022
_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
O1 O 0.3831(2) 0.53552(10) 0.8917(2) 0.0624(6) Uani 1 1 d . . .
H1A H 0.4581 0.5201 0.9495 0.094 Uiso 1 1 calc R . .
O2 O 0.4809(3) 0.56441(13) 0.6428(3) 0.0780(8) Uani 1 1 d . . .
O3 O 0.6360(3) 0.56945(12) 0.8529(3) 0.0753(8) Uani 1 1 d . . .
N1 N 0.2746(2) 0.63987(11) 0.6756(2) 0.0402(5) Uani 1 1 d . . .
C1 C 0.2295(3) 0.62972(13) 0.8581(3) 0.0424(6) Uani 1 1 d . . .
C2 C 0.1446(4) 0.63184(18) 0.9266(3) 0.0603(9) Uani 1 1 d . . .
H2A H 0.1842 0.6214 1.0158 0.072 Uiso 1 1 calc R . .
C3 C -0.0018(4) 0.64997(19) 0.8598(4) 0.0683(10) Uani 1 1 d . . .
H3A H -0.0610 0.6515 0.9045 0.082 Uiso 1 1 calc R . .
C4 C -0.0593(3) 0.66547(17) 0.7289(4) 0.0601(8) Uani 1 1 d . . .
H4A H -0.1576 0.6770 0.6857 0.072 Uiso 1 1 calc R . .
C5 C 0.0255(3) 0.66434(14) 0.6595(3) 0.0481(7) Uani 1 1 d . . .
H5A H -0.0139 0.6759 0.5708 0.058 Uiso 1 1 calc R . .
C6 C 0.1703(3) 0.64566(12) 0.7252(3) 0.0385(6) Uani 1 1 d . . .
C7 C 0.1443(3) 0.63182(14) 0.4331(3) 0.0445(7) Uani 1 1 d . . .
C8 C 0.1239(4) 0.56425(16) 0.4358(3) 0.0565(8) Uani 1 1 d . . .
H8A H 0.1757 0.5404 0.5129 0.068 Uiso 1 1 calc R . .
C9 C 0.0260(4) 0.53075(19) 0.3239(4) 0.0708(10) Uani 1 1 d . . .
H9A H 0.0127 0.4849 0.3271 0.085 Uiso 1 1 calc R . .
C10 C -0.0495(4) 0.5645(3) 0.2108(4) 0.0819(12) Uani 1 1 d . . .
H10A H -0.1137 0.5421 0.1359 0.098 Uiso 1 1 calc R . .
C11 C -0.0303(4) 0.6328(2) 0.2079(4) 0.0802(12) Uani 1 1 d . . .
H11A H -0.0832 0.6564 0.1308 0.096 Uiso 1 1 calc R . .
C12 C 0.0650(4) 0.66602(19) 0.3163(3) 0.0619(9) Uani 1 1 d . . .
H12A H 0.0772 0.7120 0.3123 0.074 Uiso 1 1 calc R . .
C13 C 0.4938(3) 0.70583(13) 0.8145(3) 0.0418(6) Uani 1 1 d . . .
C14 C 0.4211(4) 0.75986(15) 0.8347(4) 0.0592(9) Uani 1 1 d . . .
H14A H 0.3278 0.7540 0.8305 0.071 Uiso 1 1 calc R . .
C15 C 0.4846(4) 0.82299(15) 0.8612(3) 0.0600(9) Uani 1 1 d . . .
H15A H 0.4333 0.8583 0.8756 0.072 Uiso 1 1 calc R . .
C16 C 0.6214(3) 0.83455(15) 0.8666(3) 0.0508(7) Uani 1 1 d . . .
C17 C 0.6912(3) 0.78076(17) 0.8426(4) 0.0661(9) Uani 1 1 d . . .
H17A H 0.7828 0.7870 0.8432 0.079 Uiso 1 1 calc R . .
C18 C 0.6295(3) 0.71803(16) 0.8175(4) 0.0599(9) Uani 1 1 d . . .
H18A H 0.6808 0.6829 0.8023 0.072 Uiso 1 1 calc R . .
C19 C 0.4209(3) 0.63632(13) 0.7855(3) 0.0427(7) Uani 1 1 d . . .
C20 C 0.3859(3) 0.60759(14) 0.9013(3) 0.0451(7) Uani 1 1 d . . .
C21 C 0.2502(3) 0.67061(14) 0.5510(3) 0.0472(7) Uani 1 1 d . . .
H21A H 0.3431 0.6744 0.5452 0.057 Uiso 1 1 calc R . .
H21B H 0.2125 0.7155 0.5484 0.057 Uiso 1 1 calc R . .
C22 C 0.4913(4) 0.62835(19) 1.0372(3) 0.0664(9) Uani 1 1 d . . .
H22A H 0.4625 0.6087 1.1006 0.100 Uiso 1 1 calc R . .
H22B H 0.4910 0.6762 1.0442 0.100 Uiso 1 1 calc R . .
H22C H 0.5880 0.6134 1.0537 0.100 Uiso 1 1 calc R . .
C23 C 0.6891(4) 0.90312(17) 0.8930(4) 0.0705(10) Uani 1 1 d . . .
H23A H 0.7842 0.9011 0.8930 0.106 Uiso 1 1 calc R . .
H23B H 0.6984 0.9186 0.9772 0.106 Uiso 1 1 calc R . .
H23C H 0.6281 0.9334 0.8257 0.106 Uiso 1 1 calc R . .
C24 C 0.5141(4) 0.58599(16) 0.7516(5) 0.0656(10) Uani 1 1 d . . .
C25 C 0.7222(5) 0.5208(3) 0.8142(6) 0.1139(17) Uani 1 1 d . . .
H25A H 0.8102 0.5094 0.8900 0.171 Uiso 1 1 calc R . .
H25B H 0.7471 0.5405 0.7484 0.171 Uiso 1 1 calc R . .
H25C H 0.6651 0.4812 0.7794 0.171 Uiso 1 1 calc R . .

loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
O1 0.0541(13) 0.0420(12) 0.0739(15) 0.0151(10) 0.0107(11) 0.0028(10)
O2 0.0803(17) 0.0626(16) 0.108(2) -0.0256(15) 0.0561(16) 0.0030(12)
O3 0.0533(14) 0.0599(15) 0.108(2) -0.0046(13) 0.0297(14) 0.0163(11)
N1 0.0410(12) 0.0429(13) 0.0375(12) -0.0014(10) 0.0174(10) -0.0025(10)
C1 0.0448(15) 0.0378(15) 0.0458(15) 0.0017(12) 0.0204(13) -0.0002(12)
C2 0.066(2) 0.071(2) 0.0517(18) 0.0045(16) 0.0324(17) 0.0002(17)
C3 0.058(2) 0.086(3) 0.078(3) -0.007(2) 0.0449(19) 0.0009(18)
C4 0.0404(16) 0.069(2) 0.070(2) -0.0077(17) 0.0223(16) 0.0030(15)
C5 0.0457(16) 0.0473(17) 0.0457(16) -0.0056(13) 0.0139(13) 0.0025(13)
C6 0.0408(15) 0.0316(13) 0.0433(15) -0.0030(11) 0.0182(12) -0.0010(11)
C7 0.0520(17) 0.0460(16) 0.0403(15) -0.0015(12) 0.0240(14) 0.0002(13)
C8 0.066(2) 0.0447(18) 0.0547(18) -0.0051(14) 0.0211(16) -0.0002(14)
C9 0.070(2) 0.058(2) 0.076(3) -0.0245(19) 0.023(2) -0.0048(17)
C10 0.066(2) 0.109(4) 0.059(2) -0.033(2) 0.0160(19) -0.015(2)
C11 0.071(2) 0.112(4) 0.045(2) 0.005(2) 0.0116(18) -0.007(2)
C12 0.068(2) 0.068(2) 0.0507(19) 0.0092(16) 0.0262(17) -0.0027(17)
C13 0.0406(15) 0.0386(15) 0.0443(15) -0.0027(12) 0.0163(12) -0.0006(12)
C14 0.0571(19) 0.0447(18) 0.092(2) -0.0084(16) 0.0475(19) -0.0040(14)
C15 0.075(2) 0.0382(17) 0.080(2) -0.0074(15) 0.0452(19) -0.0015(15)
C16 0.0544(18) 0.0445(17) 0.0436(16) -0.0003(13) 0.0114(14) -0.0102(14)
C17 0.0404(17) 0.058(2) 0.094(3) -0.0020(18) 0.0229(17) -0.0054(15)
C18 0.0406(17) 0.0470(18) 0.092(2) -0.0099(17) 0.0284(17) -0.0018(13)
C19 0.0380(14) 0.0372(15) 0.0514(16) -0.0024(12) 0.0176(13) 0.0009(12)
C20 0.0442(16) 0.0386(16) 0.0461(16) 0.0037(12) 0.0129(13) -0.0012(12)
C21 0.0595(18) 0.0415(15) 0.0444(16) -0.0018(12) 0.0258(14) -0.0052(13)
C22 0.060(2) 0.074(2) 0.0503(19) 0.0114(16) 0.0095(16) -0.0049(17)
C23 0.067(2) 0.050(2) 0.074(2) -0.0032(17) 0.0098(19) -0.0148(16)
C24 0.056(2) 0.0395(17) 0.116(3) -0.0087(19) 0.052(2) -0.0017(15)
C25 0.094(3) 0.091(3) 0.163(5) 0.003(3) 0.061(4) 0.026(3)

_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
O1 C20 1.444(3) . ?
O1 H1A 0.8200 . ?
O2 C24 1.201(5) . ?
O3 C24 1.314(5) . ?
O3 C25 1.487(5) . ?
N1 C6 1.390(3) . ?
N1 C21 1.449(3) . ?
N1 C19 1.469(3) . ?
C1 C2 1.374(4) . ?
C1 C6 1.387(4) . ?
C1 C20 1.508(4) . ?
C2 C3 1.391(5) . ?
C2 H2A 0.9300 . ?
C3 C4 1.366(5) . ?
C3 H3A 0.9300 . ?
C4 C5 1.381(4) . ?
C4 H4A 0.9300 . ?
C5 C6 1.380(4) . ?
C5 H5A 0.9300 . ?
C7 C8 1.368(4) . ?
C7 C12 1.391(4) . ?
C7 C21 1.514(4) . ?
C8 C9 1.395(5) . ?
C8 H8A 0.9300 . ?
C9 C10 1.351(6) . ?
C9 H9A 0.9300 . ?
C10 C11 1.380(6) . ?
C10 H10A 0.9300 . ?
C11 C12 1.361(5) . ?
C11 H11A 0.9300 . ?
C12 H12A 0.9300 . ?
C13 C14 1.377(4) . ?
C13 C18 1.378(4) . ?
C13 C19 1.541(4) . ?
C14 C15 1.389(4) . ?
C14 H14A 0.9300 . ?
C15 C16 1.375(4) . ?
C15 H15A 0.9300 . ?
C16 C17 1.374(5) . ?
C16 C23 1.504(4) . ?
C17 C18 1.375(5) . ?
C17 H17A 0.9300 . ?
C18 H18A 0.9300 . ?
C19 C24 1.532(4) . ?
C19 C20 1.591(4) . ?
C20 C22 1.500(4) . ?
C21 H21A 0.9700 . ?
C21 H21B 0.9700 . ?
C22 H22A 0.9600 . ?
C22 H22B 0.9600 . ?
C22 H22C 0.9600 . ?
C23 H23A 0.9600 . ?
C23 H23B 0.9600 . ?
C23 H23C 0.9600 . ?
C25 H25A 0.9600 . ?
C25 H25B 0.9600 . ?
C25 H25C 0.9600 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C20 O1 H1A 109.5 . . ?
C24 O3 C25 111.2(3) . . ?
C6 N1 C21 120.3(2) . . ?
C6 N1 C19 109.2(2) . . ?
C21 N1 C19 121.9(2) . . ?
C2 C1 C6 120.6(3) . . ?
C2 C1 C20 130.2(3) . . ?
C6 C1 C20 109.1(2) . . ?
C1 C2 C3 118.6(3) . . ?
C1 C2 H2A 120.7 . . ?
C3 C2 H2A 120.7 . . ?
C4 C3 C2 120.5(3) . . ?
C4 C3 H3A 119.8 . . ?
C2 C3 H3A 119.8 . . ?
C3 C4 C5 121.4(3) . . ?
C3 C4 H4A 119.3 . . ?
C5 C4 H4A 119.3 . . ?
C6 C5 C4 118.2(3) . . ?
C6 C5 H5A 120.9 . . ?
C4 C5 H5A 120.9 . . ?
C5 C6 C1 120.7(3) . . ?
C5 C6 N1 128.2(2) . . ?
C1 C6 N1 111.0(2) . . ?
C8 C7 C12 118.3(3) . . ?
C8 C7 C21 122.9(3) . . ?
C12 C7 C21 118.8(3) . . ?
C7 C8 C9 120.6(3) . . ?
C7 C8 H8A 119.7 . . ?
C9 C8 H8A 119.7 . . ?
C10 C9 C8 120.4(4) . . ?
C10 C9 H9A 119.8 . . ?
C8 C9 H9A 119.8 . . ?
C9 C10 C11 119.2(3) . . ?
C9 C10 H10A 120.4 . . ?
C11 C10 H10A 120.4 . . ?
C12 C11 C10 121.0(4) . . ?
C12 C11 H11A 119.5 . . ?
C10 C11 H11A 119.5 . . ?
C11 C12 C7 120.5(4) . . ?
C11 C12 H12A 119.7 . . ?
C7 C12 H12A 119.7 . . ?
C14 C13 C18 116.8(3) . . ?
C14 C13 C19 120.1(2) . . ?
C18 C13 C19 123.1(2) . . ?
C13 C14 C15 121.2(3) . . ?
C13 C14 H14A 119.4 . . ?
C15 C14 H14A 119.4 . . ?
C16 C15 C14 121.7(3) . . ?
C16 C15 H15A 119.2 . . ?
C14 C15 H15A 119.2 . . ?
C17 C16 C15 116.7(3) . . ?
C17 C16 C23 121.6(3) . . ?
C15 C16 C23 121.7(3) . . ?
C16 C17 C18 121.9(3) . . ?
C16 C17 H17A 119.0 . . ?
C18 C17 H17A 119.0 . . ?
C17 C18 C13 121.7(3) . . ?
C17 C18 H18A 119.1 . . ?
C13 C18 H18A 119.1 . . ?
N1 C19 C24 109.1(3) . . ?
N1 C19 C13 110.7(2) . . ?
C24 C19 C13 110.8(2) . . ?
N1 C19 C20 102.2(2) . . ?
C24 C19 C20 109.8(2) . . ?
C13 C19 C20 113.9(2) . . ?
O1 C20 C22 109.6(2) . . ?
O1 C20 C1 106.5(2) . . ?
C22 C20 C1 116.1(3) . . ?
O1 C20 C19 107.7(2) . . ?
C22 C20 C19 115.0(2) . . ?
C1 C20 C19 101.3(2) . . ?
N1 C21 C7 113.2(2) . . ?
N1 C21 H21A 108.9 . . ?
C7 C21 H21A 108.9 . . ?
N1 C21 H21B 108.9 . . ?
C7 C21 H21B 108.9 . . ?
H21A C21 H21B 107.8 . . ?
C20 C22 H22A 109.5 . . ?
C20 C22 H22B 109.5 . . ?
H22A C22 H22B 109.5 . . ?
C20 C22 H22C 109.5 . . ?
H22A C22 H22C 109.5 . . ?
H22B C22 H22C 109.5 . . ?
C16 C23 H23A 109.5 . . ?
C16 C23 H23B 109.5 . . ?
H23A C23 H23B 109.5 . . ?
C16 C23 H23C 109.5 . . ?
H23A C23 H23C 109.5 . . ?
H23B C23 H23C 109.5 . . ?
O2 C24 O3 122.9(3) . . ?
O2 C24 C19 123.6(4) . . ?
O3 C24 C19 113.5(3) . . ?
O3 C25 H25A 109.5 . . ?
O3 C25 H25B 109.5 . . ?
H25A C25 H25B 109.5 . . ?
O3 C25 H25C 109.5 . . ?
H25A C25 H25C 109.5 . . ?
H25B C25 H25C 109.5 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C6 C1 C2 C3 0.3(5) . . . . ?
C20 C1 C2 C3 -175.3(3) . . . . ?
C1 C2 C3 C4 -0.2(5) . . . . ?
C2 C3 C4 C5 -0.6(6) . . . . ?
C3 C4 C5 C6 1.3(5) . . . . ?
C4 C5 C6 C1 -1.2(4) . . . . ?
C4 C5 C6 N1 178.9(3) . . . . ?
C2 C1 C6 C5 0.4(4) . . . . ?
C20 C1 C6 C5 176.8(2) . . . . ?
C2 C1 C6 N1 -179.7(3) . . . . ?
C20 C1 C6 N1 -3.2(3) . . . . ?
C21 N1 C6 C5 16.5(4) . . . . ?
C19 N1 C6 C5 165.0(3) . . . . ?
C21 N1 C6 C1 -163.4(2) . . . . ?
C19 N1 C6 C1 -14.9(3) . . . . ?
C12 C7 C8 C9 0.1(5) . . . . ?
C21 C7 C8 C9 -179.3(3) . . . . ?
C7 C8 C9 C10 0.4(5) . . . . ?
C8 C9 C10 C11 -0.9(6) . . . . ?
C9 C10 C11 C12 1.0(6) . . . . ?
C10 C11 C12 C7 -0.6(6) . . . . ?
C8 C7 C12 C11 0.1(5) . . . . ?
C21 C7 C12 C11 179.4(3) . . . . ?
C18 C13 C14 C15 -2.1(5) . . . . ?
C19 C13 C14 C15 179.9(3) . . . . ?
C13 C14 C15 C16 0.9(5) . . . . ?
C14 C15 C16 C17 1.0(5) . . . . ?
C14 C15 C16 C23 178.9(3) . . . . ?
C15 C16 C17 C18 -1.6(5) . . . . ?
C23 C16 C17 C18 -179.6(3) . . . . ?
C16 C17 C18 C13 0.4(6) . . . . ?
C14 C13 C18 C17 1.5(5) . . . . ?
C19 C13 C18 C17 179.4(3) . . . . ?
C6 N1 C19 C24 141.3(2) . . . . ?
C21 N1 C19 C24 -70.8(3) . . . . ?
C6 N1 C19 C13 -96.4(2) . . . . ?
C21 N1 C19 C13 51.4(3) . . . . ?
C6 N1 C19 C20 25.1(3) . . . . ?
C21 N1 C19 C20 173.0(2) . . . . ?
C14 C13 C19 N1 52.5(4) . . . . ?
C18 C13 C19 N1 -125.3(3) . . . . ?
C14 C13 C19 C24 173.7(3) . . . . ?
C18 C13 C19 C24 -4.1(4) . . . . ?
C14 C13 C19 C20 -61.9(4) . . . . ?
C18 C13 C19 C20 120.2(3) . . . . ?
C2 C1 C20 O1 81.5(4) . . . . ?
C6 C1 C20 O1 -94.5(3) . . . . ?
C2 C1 C20 C22 -40.7(4) . . . . ?
C6 C1 C20 C22 143.3(3) . . . . ?
C2 C1 C20 C19 -166.0(3) . . . . ?
C6 C1 C20 C19 18.0(3) . . . . ?
N1 C19 C20 O1 86.3(2) . . . . ?
C24 C19 C20 O1 -29.4(3) . . . . ?
C13 C19 C20 O1 -154.3(2) . . . . ?
N1 C19 C20 C22 -151.2(3) . . . . ?
C24 C19 C20 C22 93.1(3) . . . . ?
C13 C19 C20 C22 -31.9(3) . . . . ?
N1 C19 C20 C1 -25.2(2) . . . . ?
C24 C19 C20 C1 -140.9(3) . . . . ?
C13 C19 C20 C1 94.2(3) . . . . ?
C6 N1 C21 C7 -76.9(3) . . . . ?
C19 N1 C21 C7 138.6(3) . . . . ?
C8 C7 C21 N1 -27.0(4) . . . . ?
C12 C7 C21 N1 153.7(3) . . . . ?
C25 O3 C24 O2 -0.9(5) . . . . ?
C25 O3 C24 C19 -179.7(3) . . . . ?
N1 C19 C24 O2 13.9(4) . . . . ?
C13 C19 C24 O2 -108.2(3) . . . . ?
C20 C19 C24 O2 125.1(3) . . . . ?
N1 C19 C24 O3 -167.3(2) . . . . ?
C13 C19 C24 O3 70.5(3) . . . . ?
C20 C19 C24 O3 -56.1(3) . . . . ?

_diffrn_measured_fraction_theta_max 0.990
_diffrn_reflns_theta_full        25.01
_diffrn_measured_fraction_theta_full 0.990
_refine_diff_density_max         1.183
_refine_diff_density_min         -0.272
_refine_diff_density_rms         0.048
_database_code_depnum_ccdc_archive 'CCDC 957673'
#######################################################################
#
#                 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_z

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C24 H21 N O3'
_chemical_formula_weight         371.42

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

_cell_length_a                   10.7586(6)
_cell_length_b                   16.5601(10)
_cell_length_c                   21.4710(13)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_volume                     3825.3(4)
_cell_formula_units_Z            8
_cell_measurement_temperature    173(2)
_cell_measurement_reflns_used    ?
_cell_measurement_theta_min      ?
_cell_measurement_theta_max      ?

_exptl_crystal_description       block
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.55
_exptl_crystal_size_mid          0.45
_exptl_crystal_size_min          0.24
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.290
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1568
_exptl_absorpt_coefficient_mu    0.085
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.9548
_exptl_absorpt_correction_T_max  0.9799
_exptl_absorpt_process_details   ?

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      173(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  ?
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            41206
_diffrn_reflns_av_R_equivalents  0.0502
_diffrn_reflns_av_sigmaI/netI    0.0195
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_k_min       -19
_diffrn_reflns_limit_k_max       19
_diffrn_reflns_limit_l_min       -25
_diffrn_reflns_limit_l_max       25
_diffrn_reflns_theta_min         1.90
_diffrn_reflns_theta_max         25.01
_reflns_number_total             3370
_reflns_number_gt                2837
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_molecular_graphics    ?
_computing_publication_material  ?

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

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[\s^2^(Fo^2^)+(0.0630P)^2^+2.7536P] where P=(Fo^2^+2Fc^2^)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         3370
_refine_ls_number_parameters     253
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0550
_refine_ls_R_factor_gt           0.0460
_refine_ls_wR_factor_ref         0.1283
_refine_ls_wR_factor_gt          0.1189
_refine_ls_goodness_of_fit_ref   1.026
_refine_ls_restrained_S_all      1.026
_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
O1 O 1.08138(12) 0.00005(9) 0.72767(6) 0.0383(4) Uani 1 1 d . . .
O2 O 0.87772(12) 0.01662(8) 0.71679(6) 0.0333(3) Uani 1 1 d . . .
O3 O 1.16369(11) -0.08369(8) 0.82792(6) 0.0303(3) Uani 1 1 d . . .
H3B H 1.1710 -0.0587 0.7941 0.046 Uiso 1 1 calc R . .
N1 N 0.82783(13) -0.05725(9) 0.82380(6) 0.0247(3) Uani 1 1 d . . .
H1B H 0.7512 -0.0741 0.8177 0.030 Uiso 1 1 calc R . .
C1 C 1.19665(19) -0.31506(12) 0.97044(9) 0.0340(5) Uani 1 1 d . . .
H1A H 1.2766 -0.2979 0.9571 0.041 Uiso 1 1 calc R . .
C2 C 1.1869(2) -0.37612(13) 1.01422(10) 0.0405(5) Uani 1 1 d . . .
H2A H 1.2598 -0.4002 1.0308 0.049 Uiso 1 1 calc R . .
C3 C 1.0717(2) -0.40189(14) 1.03372(11) 0.0466(6) Uani 1 1 d . . .
H3A H 1.0650 -0.4432 1.0642 0.056 Uiso 1 1 calc R . .
C4 C 0.9654(2) -0.36742(14) 1.00875(12) 0.0482(6) Uani 1 1 d . . .
H4A H 0.8857 -0.3857 1.0216 0.058 Uiso 1 1 calc R . .
C5 C 0.9755(2) -0.30648(12) 0.96514(10) 0.0388(5) Uani 1 1 d . . .
H5A H 0.9022 -0.2833 0.9481 0.047 Uiso 1 1 calc R . .
C6 C 1.09124(17) -0.27835(11) 0.94567(8) 0.0271(4) Uani 1 1 d . . .
C7 C 1.10640(17) -0.21047(11) 0.90211(8) 0.0279(4) Uani 1 1 d . . .
H7A H 1.1868 -0.2024 0.8849 0.034 Uiso 1 1 calc R . .
C8 C 1.01811(17) -0.15976(11) 0.88487(8) 0.0251(4) Uani 1 1 d . . .
H8A H 0.9358 -0.1710 0.8983 0.030 Uiso 1 1 calc R . .
C9 C 1.03787(16) -0.08542(10) 0.84554(8) 0.0244(4) Uani 1 1 d . . .
C10 C 0.99262(17) -0.01255(10) 0.88217(8) 0.0247(4) Uani 1 1 d . . .
C11 C 0.86773(17) -0.00014(10) 0.86783(8) 0.0244(4) Uani 1 1 d . . .
C12 C 0.80003(18) 0.06076(11) 0.89621(8) 0.0296(4) Uani 1 1 d . . .
H12A H 0.7149 0.0693 0.8866 0.035 Uiso 1 1 calc R . .
C13 C 0.86169(19) 0.10901(11) 0.93942(9) 0.0329(4) Uani 1 1 d . . .
H13A H 0.8175 0.1512 0.9597 0.039 Uiso 1 1 calc R . .
C14 C 0.98591(19) 0.09691(11) 0.95359(8) 0.0317(4) Uani 1 1 d . . .
H14A H 1.0259 0.1312 0.9829 0.038 Uiso 1 1 calc R . .
C15 C 1.05259(18) 0.03506(11) 0.92535(8) 0.0285(4) Uani 1 1 d . . .
H15A H 1.1373 0.0259 0.9356 0.034 Uiso 1 1 calc R . .
C16 C 0.9993(2) -0.18348(14) 0.70664(10) 0.0433(5) Uani 1 1 d . . .
H16A H 1.0590 -0.1458 0.6918 0.052 Uiso 1 1 calc R . .
C17 C 0.9880(2) -0.25842(15) 0.67802(12) 0.0549(7) Uani 1 1 d . . .
H17A H 1.0396 -0.2716 0.6436 0.066 Uiso 1 1 calc R . .
C18 C 0.9032(2) -0.31323(13) 0.69917(12) 0.0506(6) Uani 1 1 d . . .
H18A H 0.8966 -0.3646 0.6797 0.061 Uiso 1 1 calc R . .
C19 C 0.8271(2) -0.29429(13) 0.74871(11) 0.0478(6) Uani 1 1 d . . .
H19A H 0.7680 -0.3325 0.7634 0.057 Uiso 1 1 calc R . .
C20 C 0.8369(2) -0.21929(12) 0.77712(9) 0.0366(5) Uani 1 1 d . . .
H20A H 0.7835 -0.2059 0.8108 0.044 Uiso 1 1 calc R . .
C21 C 0.92422(17) -0.16369(11) 0.75653(8) 0.0274(4) Uani 1 1 d . . .
C22 C 0.93924(16) -0.08330(10) 0.79000(8) 0.0236(4) Uani 1 1 d . . .
C23 C 0.97655(17) -0.01798(11) 0.74212(8) 0.0254(4) Uani 1 1 d . . .
C24 C 0.9022(2) 0.07519(14) 0.66791(10) 0.0427(5) Uani 1 1 d . . .
H24A H 0.8233 0.0970 0.6524 0.064 Uiso 1 1 calc R . .
H24B H 0.9467 0.0489 0.6337 0.064 Uiso 1 1 calc R . .
H24C H 0.9530 0.1193 0.6846 0.064 Uiso 1 1 calc R . .

loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
O1 0.0266(8) 0.0438(9) 0.0445(8) 0.0127(6) 0.0091(6) 0.0025(6)
O2 0.0285(7) 0.0391(8) 0.0322(7) 0.0106(6) -0.0019(6) 0.0015(6)
O3 0.0216(7) 0.0375(7) 0.0319(7) 0.0019(6) 0.0031(5) 0.0018(6)
N1 0.0178(7) 0.0263(8) 0.0299(8) -0.0027(6) 0.0033(6) -0.0010(6)
C1 0.0320(10) 0.0335(10) 0.0365(10) -0.0005(8) -0.0041(8) 0.0040(8)
C2 0.0419(12) 0.0383(12) 0.0414(11) 0.0060(9) -0.0101(9) 0.0087(9)
C3 0.0553(15) 0.0367(12) 0.0479(13) 0.0131(10) -0.0010(11) 0.0030(10)
C4 0.0400(13) 0.0427(13) 0.0620(15) 0.0148(11) 0.0024(11) -0.0017(10)
C5 0.0324(11) 0.0330(11) 0.0512(12) 0.0072(9) -0.0050(9) 0.0038(9)
C6 0.0305(10) 0.0222(9) 0.0287(9) -0.0053(7) -0.0045(8) 0.0037(7)
C7 0.0268(9) 0.0273(9) 0.0297(9) -0.0037(8) -0.0011(8) 0.0018(8)
C8 0.0243(9) 0.0248(9) 0.0260(9) -0.0029(7) -0.0004(7) -0.0007(7)
C9 0.0204(9) 0.0257(9) 0.0269(9) -0.0003(7) 0.0007(7) 0.0003(7)
C10 0.0291(10) 0.0215(9) 0.0235(8) 0.0038(7) 0.0032(7) -0.0005(7)
C11 0.0275(9) 0.0215(8) 0.0242(8) 0.0026(7) 0.0052(7) -0.0014(7)
C12 0.0286(10) 0.0268(10) 0.0333(10) 0.0020(8) 0.0074(8) 0.0012(8)
C13 0.0436(12) 0.0235(9) 0.0317(10) -0.0018(8) 0.0120(9) 0.0005(8)
C14 0.0437(12) 0.0258(9) 0.0256(9) -0.0017(7) 0.0034(8) -0.0079(8)
C15 0.0314(10) 0.0286(10) 0.0256(9) 0.0031(7) 0.0000(7) -0.0042(8)
C16 0.0402(12) 0.0407(12) 0.0489(12) -0.0154(10) 0.0092(10) -0.0009(10)
C17 0.0528(14) 0.0510(14) 0.0609(15) -0.0279(12) 0.0082(12) 0.0033(12)
C18 0.0625(16) 0.0315(11) 0.0580(14) -0.0181(10) -0.0140(12) 0.0074(11)
C19 0.0618(16) 0.0302(11) 0.0515(12) -0.0045(10) -0.0084(11) -0.0090(10)
C20 0.0417(12) 0.0307(11) 0.0376(10) -0.0040(8) -0.0028(9) -0.0028(9)
C21 0.0280(10) 0.0245(9) 0.0297(9) -0.0031(7) -0.0066(8) 0.0041(8)
C22 0.0215(9) 0.0240(9) 0.0253(8) -0.0012(7) 0.0012(7) 0.0019(7)
C23 0.0256(10) 0.0263(9) 0.0244(9) -0.0031(7) 0.0012(7) 0.0029(8)
C24 0.0414(12) 0.0492(13) 0.0376(11) 0.0177(10) 0.0020(9) 0.0068(10)

_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
O1 C23 1.207(2) . ?
O2 C23 1.325(2) . ?
O2 C24 1.453(2) . ?
O3 C9 1.406(2) . ?
O3 H3B 0.8400 . ?
N1 C11 1.404(2) . ?
N1 C22 1.466(2) . ?
N1 H1B 0.8800 . ?
C1 C2 1.385(3) . ?
C1 C6 1.392(3) . ?
C1 H1A 0.9500 . ?
C2 C3 1.376(3) . ?
C2 H2A 0.9500 . ?
C3 C4 1.386(3) . ?
C3 H3A 0.9500 . ?
C4 C5 1.381(3) . ?
C4 H4A 0.9500 . ?
C5 C6 1.394(3) . ?
C5 H5A 0.9500 . ?
C6 C7 1.471(3) . ?
C7 C8 1.321(3) . ?
C7 H7A 0.9500 . ?
C8 C9 1.508(2) . ?
C8 H8A 0.9500 . ?
C9 C10 1.520(2) . ?
C9 C22 1.597(2) . ?
C10 C15 1.377(3) . ?
C10 C11 1.394(3) . ?
C11 C12 1.385(2) . ?
C12 C13 1.393(3) . ?
C12 H12A 0.9500 . ?
C13 C14 1.385(3) . ?
C13 H13A 0.9500 . ?
C14 C15 1.390(3) . ?
C14 H14A 0.9500 . ?
C15 H15A 0.9500 . ?
C16 C21 1.381(3) . ?
C16 C17 1.390(3) . ?
C16 H16A 0.9500 . ?
C17 C18 1.365(4) . ?
C17 H17A 0.9500 . ?
C18 C19 1.379(4) . ?
C18 H18A 0.9500 . ?
C19 C20 1.388(3) . ?
C19 H19A 0.9500 . ?
C20 C21 1.388(3) . ?
C20 H20A 0.9500 . ?
C21 C22 1.521(2) . ?
C22 C23 1.545(2) . ?
C24 H24A 0.9800 . ?
C24 H24B 0.9800 . ?
C24 H24C 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 116.10(15) . . ?
C9 O3 H3B 109.5 . . ?
C11 N1 C22 106.35(13) . . ?
C11 N1 H1B 126.8 . . ?
C22 N1 H1B 126.8 . . ?
C2 C1 C6 121.1(2) . . ?
C2 C1 H1A 119.4 . . ?
C6 C1 H1A 119.4 . . ?
C3 C2 C1 120.08(19) . . ?
C3 C2 H2A 120.0 . . ?
C1 C2 H2A 120.0 . . ?
C2 C3 C4 119.8(2) . . ?
C2 C3 H3A 120.1 . . ?
C4 C3 H3A 120.1 . . ?
C5 C4 C3 119.9(2) . . ?
C5 C4 H4A 120.0 . . ?
C3 C4 H4A 120.0 . . ?
C4 C5 C6 121.17(19) . . ?
C4 C5 H5A 119.4 . . ?
C6 C5 H5A 119.4 . . ?
C1 C6 C5 117.86(18) . . ?
C1 C6 C7 119.09(18) . . ?
C5 C6 C7 123.02(17) . . ?
C8 C7 C6 125.74(18) . . ?
C8 C7 H7A 117.1 . . ?
C6 C7 H7A 117.1 . . ?
C7 C8 C9 125.07(17) . . ?
C7 C8 H8A 117.5 . . ?
C9 C8 H8A 117.5 . . ?
O3 C9 C8 107.64(14) . . ?
O3 C9 C10 115.55(14) . . ?
C8 C9 C10 108.24(14) . . ?
O3 C9 C22 116.01(14) . . ?
C8 C9 C22 110.03(14) . . ?
C10 C9 C22 98.98(13) . . ?
C15 C10 C11 121.05(17) . . ?
C15 C10 C9 130.73(17) . . ?
C11 C10 C9 108.15(15) . . ?
C12 C11 C10 121.14(17) . . ?
C12 C11 N1 128.73(17) . . ?
C10 C11 N1 110.12(15) . . ?
C11 C12 C13 117.41(18) . . ?
C11 C12 H12A 121.3 . . ?
C13 C12 H12A 121.3 . . ?
C14 C13 C12 121.53(17) . . ?
C14 C13 H13A 119.2 . . ?
C12 C13 H13A 119.2 . . ?
C13 C14 C15 120.58(18) . . ?
C13 C14 H14A 119.7 . . ?
C15 C14 H14A 119.7 . . ?
C10 C15 C14 118.28(18) . . ?
C10 C15 H15A 120.9 . . ?
C14 C15 H15A 120.9 . . ?
C21 C16 C17 120.2(2) . . ?
C21 C16 H16A 119.9 . . ?
C17 C16 H16A 119.9 . . ?
C18 C17 C16 120.3(2) . . ?
C18 C17 H17A 119.8 . . ?
C16 C17 H17A 119.8 . . ?
C17 C18 C19 120.2(2) . . ?
C17 C18 H18A 119.9 . . ?
C19 C18 H18A 119.9 . . ?
C18 C19 C20 119.8(2) . . ?
C18 C19 H19A 120.1 . . ?
C20 C19 H19A 120.1 . . ?
C19 C20 C21 120.3(2) . . ?
C19 C20 H20A 119.8 . . ?
C21 C20 H20A 119.8 . . ?
C16 C21 C20 119.06(18) . . ?
C16 C21 C22 120.78(17) . . ?
C20 C21 C22 120.13(17) . . ?
N1 C22 C21 113.85(14) . . ?
N1 C22 C23 109.62(14) . . ?
C21 C22 C23 109.01(14) . . ?
N1 C22 C9 100.38(13) . . ?
C21 C22 C9 113.84(14) . . ?
C23 C22 C9 109.85(14) . . ?
O1 C23 O2 122.51(17) . . ?
O1 C23 C22 125.93(16) . . ?
O2 C23 C22 111.56(15) . . ?
O2 C24 H24A 109.5 . . ?
O2 C24 H24B 109.5 . . ?
H24A C24 H24B 109.5 . . ?
O2 C24 H24C 109.5 . . ?
H24A C24 H24C 109.5 . . ?
H24B C24 H24C 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
C6 C1 C2 C3 0.4(3) . . . . ?
C1 C2 C3 C4 1.0(3) . . . . ?
C2 C3 C4 C5 -1.0(4) . . . . ?
C3 C4 C5 C6 -0.3(4) . . . . ?
C2 C1 C6 C5 -1.7(3) . . . . ?
C2 C1 C6 C7 176.37(17) . . . . ?
C4 C5 C6 C1 1.6(3) . . . . ?
C4 C5 C6 C7 -176.36(19) . . . . ?
C1 C6 C7 C8 -165.43(18) . . . . ?
C5 C6 C7 C8 12.5(3) . . . . ?
C6 C7 C8 C9 173.24(16) . . . . ?
C7 C8 C9 O3 3.7(2) . . . . ?
C7 C8 C9 C10 -121.84(19) . . . . ?
C7 C8 C9 C22 130.99(18) . . . . ?
O3 C9 C10 C15 -34.6(3) . . . . ?
C8 C9 C10 C15 86.2(2) . . . . ?
C22 C9 C10 C15 -159.16(18) . . . . ?
O3 C9 C10 C11 148.57(15) . . . . ?
C8 C9 C10 C11 -90.68(16) . . . . ?
C22 C9 C10 C11 23.98(17) . . . . ?
C15 C10 C11 C12 0.4(3) . . . . ?
C9 C10 C11 C12 177.64(15) . . . . ?
C15 C10 C11 N1 -178.69(15) . . . . ?
C9 C10 C11 N1 -1.47(18) . . . . ?
C22 N1 C11 C12 156.36(17) . . . . ?
C22 N1 C11 C10 -24.62(18) . . . . ?
C10 C11 C12 C13 0.1(3) . . . . ?
N1 C11 C12 C13 179.04(16) . . . . ?
C11 C12 C13 C14 0.1(3) . . . . ?
C12 C13 C14 C15 -0.8(3) . . . . ?
C11 C10 C15 C14 -1.1(3) . . . . ?
C9 C10 C15 C14 -177.62(17) . . . . ?
C13 C14 C15 C10 1.3(3) . . . . ?
C21 C16 C17 C18 -0.4(4) . . . . ?
C16 C17 C18 C19 0.7(4) . . . . ?
C17 C18 C19 C20 0.0(4) . . . . ?
C18 C19 C20 C21 -1.0(3) . . . . ?
C17 C16 C21 C20 -0.6(3) . . . . ?
C17 C16 C21 C22 177.4(2) . . . . ?
C19 C20 C21 C16 1.3(3) . . . . ?
C19 C20 C21 C22 -176.77(18) . . . . ?
C11 N1 C22 C21 160.22(14) . . . . ?
C11 N1 C22 C23 -77.38(16) . . . . ?
C11 N1 C22 C9 38.20(16) . . . . ?
C16 C21 C22 N1 157.34(18) . . . . ?
C20 C21 C22 N1 -24.6(2) . . . . ?
C16 C21 C22 C23 34.6(2) . . . . ?
C20 C21 C22 C23 -147.37(17) . . . . ?
C16 C21 C22 C9 -88.4(2) . . . . ?
C20 C21 C22 C9 89.6(2) . . . . ?
O3 C9 C22 N1 -160.91(14) . . . . ?
C8 C9 C22 N1 76.61(16) . . . . ?
C10 C9 C22 N1 -36.66(15) . . . . ?
O3 C9 C22 C21 77.06(19) . . . . ?
C8 C9 C22 C21 -45.42(19) . . . . ?
C10 C9 C22 C21 -158.69(14) . . . . ?
O3 C9 C22 C23 -45.51(19) . . . . ?
C8 C9 C22 C23 -167.98(14) . . . . ?
C10 C9 C22 C23 78.75(15) . . . . ?
C24 O2 C23 O1 3.0(3) . . . . ?
C24 O2 C23 C22 -175.93(15) . . . . ?
N1 C22 C23 O1 144.52(18) . . . . ?
C21 C22 C23 O1 -90.2(2) . . . . ?
C9 C22 C23 O1 35.1(2) . . . . ?
N1 C22 C23 O2 -36.56(19) . . . . ?
C21 C22 C23 O2 88.68(17) . . . . ?
C9 C22 C23 O2 -145.95(15) . . . . ?

_diffrn_measured_fraction_theta_max 1.000
_diffrn_reflns_theta_full        25.01
_diffrn_measured_fraction_theta_full 1.000
_refine_diff_density_max         0.563
_refine_diff_density_min         -0.621
_refine_diff_density_rms         0.042
_database_code_depnum_ccdc_archive 'CCDC 957672'