# Electronic Supplementary Material (ESI) for RSC Advances.
# 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_shelxl
_audit_block_doi                 10.5517/ccz7wy0
_database_code_depnum_ccdc_archive 'CCDC 901323'
_audit_update_record             
;
2015-02-01 deposited with the CCDC.
2015-04-10 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C22 H21 N O3'
_chemical_formula_weight         347.40

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           ?
_symmetry_space_group_name_H-M   ?

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                   9.3400(3)
_cell_length_b                   22.1653(8)
_cell_length_c                   8.7044(3)
_cell_angle_alpha                90.00
_cell_angle_beta                 105.5490(10)
_cell_angle_gamma                90.00
_cell_volume                     1736.07(10)
_cell_formula_units_Z            4
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    ?
_cell_measurement_theta_min      ?
_cell_measurement_theta_max      ?

_exptl_crystal_description       ?
_exptl_crystal_colour            ?
_exptl_crystal_size_max          ?
_exptl_crystal_size_mid          ?
_exptl_crystal_size_min          ?
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.329
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             736
_exptl_absorpt_coefficient_mu    0.088
_exptl_absorpt_correction_type   ?
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?

_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  ?
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            13468
_diffrn_reflns_av_R_equivalents  0.0293
_diffrn_reflns_av_sigmaI/netI    0.0205
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -23
_diffrn_reflns_limit_k_max       24
_diffrn_reflns_limit_l_min       -7
_diffrn_reflns_limit_l_max       9
_diffrn_reflns_theta_min         1.84
_diffrn_reflns_theta_max         23.20
_reflns_number_total             2471
_reflns_number_gt                2020
_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)+(0.0575P)²+0.7077P] 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         2471
_refine_ls_number_parameters     235
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0541
_refine_ls_R_factor_gt           0.0429
_refine_ls_wR_factor_ref         0.1217
_refine_ls_wR_factor_gt          0.1100
_refine_ls_goodness_of_fit_ref   1.068
_refine_ls_restrained_S_all      1.068
_refine_ls_shift/su_max          0.002
_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
O21 O 0.28854(19) 0.29181(6) 0.06272(19) 0.0557(4) Uani 1 1 d . . .
O11 O 0.71530(16) 0.00844(7) 0.09935(17) 0.0521(4) Uani 1 1 d . . .
N16 N 0.5462(2) 0.11727(8) 0.4014(2) 0.0449(5) Uani 1 1 d . . .
H16 H 0.5448 0.1478 0.4620 0.054 Uiso 1 1 calc R . .
C15 C 0.4653(2) 0.11763(9) 0.2338(2) 0.0390(5) Uani 1 1 d . . .
H15 H 0.3830 0.0888 0.2181 0.047 Uiso 1 1 calc R . .
C17 C 0.6268(2) 0.06494(9) 0.4600(2) 0.0399(5) Uani 1 1 d . . .
O22 O 0.4670(2) 0.33618(7) 0.2439(2) 0.0742(6) Uani 1 1 d . . .
C22 C 0.6631(2) 0.02270(9) 0.3580(2) 0.0402(5) Uani 1 1 d . . .
C22A C 0.6108(2) 0.03117(9) 0.1792(2) 0.0414(5) Uani 1 1 d . . .
H22 H 0.5198 0.0073 0.1414 0.050 Uiso 1 1 calc R . .
C23 C 0.4102(3) 0.28893(10) 0.1922(3) 0.0530(6) Uani 1 1 d . . .
C29A C 0.2196(3) 0.24033(9) -0.0100(3) 0.0463(6) Uani 1 1 d . . .
C25A C 0.2729(2) 0.18324(9) 0.0422(2) 0.0411(5) Uani 1 1 d . . .
C24 C 0.4616(3) 0.23006(9) 0.2514(3) 0.0480(6) Uani 1 1 d . . .
H24 H 0.5398 0.2273 0.3434 0.058 Uiso 1 1 calc R . .
C25 C 0.4017(2) 0.17888(9) 0.1797(2) 0.0409(5) Uani 1 1 d . . .
C14A C 0.5697(2) 0.09650(9) 0.1340(2) 0.0393(5) Uani 1 1 d . . .
H14 H 0.5141 0.0976 0.0212 0.047 Uiso 1 1 calc R . .
C26 C 0.1966(2) 0.13421(10) -0.0436(3) 0.0463(5) Uani 1 1 d . . .
H26 H 0.2302 0.0953 -0.0149 0.056 Uiso 1 1 calc R . .
C18 C 0.6729(2) 0.05517(10) 0.6241(3) 0.0490(6) Uani 1 1 d . . .
H18 H 0.6490 0.0831 0.6929 0.059 Uiso 1 1 calc R . .
C21 C 0.7415(2) -0.02857(10) 0.4229(3) 0.0502(6) Uani 1 1 d . . .
H21 H 0.7638 -0.0574 0.3551 0.060 Uiso 1 1 calc R . .
C28 C 0.0198(3) 0.19983(11) -0.2175(3) 0.0533(6) Uani 1 1 d . . .
C19 C 0.7530(3) 0.00481(11) 0.6850(3) 0.0542(6) Uani 1 1 d . . .
H19 H 0.7846 -0.0007 0.7948 0.065 Uiso 1 1 calc R . .
C14 C 0.7063(2) 0.13616(11) 0.1558(3) 0.0516(6) Uani 1 1 d . . .
H14A H 0.7529 0.1417 0.2687 0.062 Uiso 1 1 calc R . .
H14B H 0.6769 0.1755 0.1090 0.062 Uiso 1 1 calc R . .
C27 C 0.0734(3) 0.14253(11) -0.1691(3) 0.0515(6) Uani 1 1 d . . .
H27 H 0.0246 0.1090 -0.2230 0.062 Uiso 1 1 calc R . .
C13 C 0.8167(3) 0.10753(13) 0.0770(3) 0.0617(7) Uani 1 1 d . . .
H13C H 0.7764 0.1082 -0.0379 0.074 Uiso 1 1 calc R . .
H13D H 0.9084 0.1305 0.1035 0.074 Uiso 1 1 calc R . .
C29 C 0.0954(3) 0.24860(11) -0.1369(3) 0.0559(6) Uani 1 1 d . . .
H29 H 0.0627 0.2875 -0.1680 0.067 Uiso 1 1 calc R . .
C20 C 0.7871(3) -0.03779(11) 0.5849(3) 0.0557(6) Uani 1 1 d . . .
H20 H 0.8402 -0.0723 0.6265 0.067 Uiso 1 1 calc R . .
C12 C 0.8482(3) 0.04335(13) 0.1330(3) 0.0627(7) Uani 1 1 d . . .
H12E H 0.9171 0.0254 0.0804 0.075 Uiso 1 1 calc R . .
H12F H 0.8945 0.0431 0.2469 0.075 Uiso 1 1 calc R . .
C30 C -0.1185(3) 0.20765(14) -0.3529(3) 0.0772(8) Uani 1 1 d . . .
H30A H -0.1551 0.1688 -0.3939 0.116 Uiso 1 1 calc R . .
H30B H -0.0954 0.2310 -0.4361 0.116 Uiso 1 1 calc R . .
H30C H -0.1929 0.2281 -0.3150 0.116 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
O21 C23 1.371(3) . ?
O21 C29A 1.378(3) . ?
O11 C12 1.425(3) . ?
O11 C22A 1.433(2) . ?
N16 C17 1.402(3) . ?
N16 C15 1.452(3) . ?
C15 C25 1.506(3) . ?
C15 C14A 1.543(3) . ?
C17 C22 1.394(3) . ?
C17 C18 1.394(3) . ?
O22 C23 1.205(3) . ?
C22 C21 1.388(3) . ?
C22 C22A 1.513(3) . ?
C22A C14A 1.523(3) . ?
C23 C24 1.437(3) . ?
C29A C29 1.382(3) . ?
C29A C25A 1.391(3) . ?
C25A C26 1.400(3) . ?
C25A C25 1.455(3) . ?
C24 C25 1.343(3) . ?
C14A C14 1.519(3) . ?
C26 C27 1.370(3) . ?
C18 C19 1.369(3) . ?
C21 C20 1.375(3) . ?
C28 C29 1.376(3) . ?
C28 C27 1.389(3) . ?
C28 C30 1.507(3) . ?
C19 C20 1.378(3) . ?
C14 C13 1.522(3) . ?
C13 C12 1.507(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 O21 C29A 121.43(17) . . ?
C12 O11 C22A 112.24(16) . . ?
C17 N16 C15 117.01(16) . . ?
N16 C15 C25 112.01(16) . . ?
N16 C15 C14A 109.07(16) . . ?
C25 C15 C14A 110.69(16) . . ?
C22 C17 C18 119.2(2) . . ?
C22 C17 N16 121.49(18) . . ?
C18 C17 N16 119.32(19) . . ?
C21 C22 C17 118.87(19) . . ?
C21 C22 C22A 120.67(19) . . ?
C17 C22 C22A 120.38(18) . . ?
O11 C22A C22 112.41(16) . . ?
O11 C22A C14A 111.49(17) . . ?
C22 C22A C14A 111.93(16) . . ?
O22 C23 O21 116.8(2) . . ?
O22 C23 C24 125.7(2) . . ?
O21 C23 C24 117.4(2) . . ?
O21 C29A C29 116.48(19) . . ?
O21 C29A C25A 121.4(2) . . ?
C29 C29A C25A 122.1(2) . . ?
C29A C25A C26 116.4(2) . . ?
C29A C25A C25 118.27(19) . . ?
C26 C25A C25 125.28(19) . . ?
C25 C24 C23 122.9(2) . . ?
C24 C25 C25A 118.44(19) . . ?
C24 C25 C15 122.4(2) . . ?
C25A C25 C15 119.14(18) . . ?
C14 C14A C22A 111.90(17) . . ?
C14 C14A C15 112.99(17) . . ?
C22A C14A C15 107.27(16) . . ?
C27 C26 C25A 121.3(2) . . ?
C19 C18 C17 120.7(2) . . ?
C20 C21 C22 121.6(2) . . ?
C29 C28 C27 118.0(2) . . ?
C29 C28 C30 121.6(2) . . ?
C27 C28 C30 120.4(2) . . ?
C18 C19 C20 120.6(2) . . ?
C14A C14 C13 110.52(19) . . ?
C26 C27 C28 121.5(2) . . ?
C12 C13 C14 110.2(2) . . ?
C28 C29 C29A 120.6(2) . . ?
C21 C20 C19 119.1(2) . . ?
O11 C12 C13 111.25(19) . . ?

_diffrn_measured_fraction_theta_max 0.996
_diffrn_reflns_theta_full        23.20
_diffrn_measured_fraction_theta_full 0.996
_refine_diff_density_max         0.378
_refine_diff_density_min         -0.417
_refine_diff_density_rms         0.046
####################################################################### 
# 
# 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_shelxl
_audit_block_doi                 10.5517/ccz7wz1
_database_code_depnum_ccdc_archive 'CCDC 901324'
_audit_update_record             
;
2015-02-01 deposited with the CCDC.
2015-04-10 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C22 H21 N O3'
_chemical_formula_sum            'C22 H21 N O3'
_chemical_formula_weight         347.40

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           triclinic
_symmetry_space_group_name_H-M   P-1

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

_cell_length_a                   7.7529(4)
_cell_length_b                   11.2790(7)
_cell_length_c                   11.7563(11)
_cell_angle_alpha                117.232(3)
_cell_angle_beta                 98.475(3)
_cell_angle_gamma                101.301(2)
_cell_volume                     862.60(11)
_cell_formula_units_Z            2
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    30
_cell_measurement_theta_min      20
_cell_measurement_theta_max      25

_exptl_crystal_description       ?
_exptl_crystal_colour            ?
_exptl_crystal_size_max          0.20
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.15
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.338
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             368
_exptl_absorpt_coefficient_mu    0.089
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.982
_exptl_absorpt_correction_T_max  0.987
_exptl_absorpt_process_details   'SADABS (Bruker 1999)'


_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 axs kappa apex2 CCD Diffractometer'
_diffrn_measurement_method       'ω and φ scan'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            18945
_diffrn_reflns_av_R_equivalents  0.0303
_diffrn_reflns_av_sigmaI/netI    0.0259
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_theta_min         2.02
_diffrn_reflns_theta_max         30.18
_reflns_number_total             5009
_reflns_number_gt                3544
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'APEX2 (Bruker, 2004)'
_computing_cell_refinement       'APEX2/SAINT (Bruker, 2004)'
_computing_data_reduction        'SAINT/XPREP (Bruker, 2004)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_molecular_graphics    
'ORTEP3 (Farrugia, 1997) and Mercury (Bruno et al., 2002)'
_computing_publication_material  'PLATON (Spek, 2009)'
_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)+(0.0827P)²+0.3447P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         5009
_refine_ls_number_parameters     235
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0790
_refine_ls_R_factor_gt           0.0545
_refine_ls_wR_factor_ref         0.1764
_refine_ls_wR_factor_gt          0.1483
_refine_ls_goodness_of_fit_ref   1.033
_refine_ls_restrained_S_all      1.033
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
O2 O 0.69639(15) 0.63713(13) 0.02296(11) 0.0385(3) Uani 1 1 d . . .
C7 C 0.9273(2) 0.64223(15) -0.13810(14) 0.0305(3) Uani 1 1 d . . .
C8 C 1.0013(2) 0.66621(15) -0.00600(14) 0.0306(3) Uani 1 1 d . . .
N1 N 0.95359(19) 0.59869(13) -0.35976(12) 0.0343(3) Uani 1 1 d . . .
H H 0.9425 0.5149 -0.4199 0.041 Uiso 1 1 calc R . .
C4 C 0.8806(2) 0.66458(16) 0.07070(15) 0.0321(3) Uani 1 1 d . . .
C6 C 0.7463(2) 0.61512(17) -0.18119(16) 0.0363(3) Uani 1 1 d . . .
H6 H 0.6982 0.5978 -0.2665 0.044 Uiso 1 1 calc R . .
C11 C 1.0532(2) 0.65038(16) -0.22402(14) 0.0320(3) Uani 1 1 d . . .
H11 H 1.1325 0.5922 -0.2253 0.038 Uiso 1 1 calc R . .
C12 C 0.8757(2) 0.68235(16) -0.39430(14) 0.0315(3) Uani 1 1 d . . .
C3 C 0.9383(2) 0.69114(17) 0.19930(16) 0.0377(3) Uani 1 1 d . . .
H3 H 0.8538 0.6898 0.2476 0.045 Uiso 1 1 calc R . .
C2 C 1.1206(2) 0.71958(17) 0.25612(16) 0.0375(3) Uani 1 1 d . . .
C10 C 1.2429(2) 0.71608(18) 0.17925(17) 0.0394(4) Uani 1 1 d . . .
H011 H 1.3659 0.7322 0.2154 0.047 Uiso 1 1 calc R . .
C9 C 1.1850(2) 0.68931(18) 0.05130(16) 0.0372(3) Uani 1 1 d . . .
H9 H 1.2691 0.6865 0.0020 0.045 Uiso 1 1 calc R . .
O3 O 1.16897(19) 1.03131(13) -0.12889(13) 0.0526(4) Uani 1 1 d . . .
C19 C 1.1758(2) 0.80019(17) -0.16807(15) 0.0363(3) Uani 1 1 d . . .
H19 H 1.2389 0.8366 -0.0748 0.044 Uiso 1 1 calc R . .
O1 O 0.45952(18) 0.58805(17) -0.13623(15) 0.0564(4) Uani 1 1 d . . .
C5 C 0.6228(2) 0.61153(18) -0.10156(17) 0.0377(3) Uani 1 1 d . . .
C18 C 1.0589(2) 0.89261(16) -0.17287(16) 0.0384(4) Uani 1 1 d . . .
H18 H 0.9858 0.9001 -0.1100 0.046 Uiso 1 1 calc R . .
C17 C 0.9262(2) 0.82680(16) -0.30839(16) 0.0359(3) Uani 1 1 d . . .
C20 C 1.3203(2) 0.8037(2) -0.24303(18) 0.0419(4) Uani 1 1 d . . .
H20A H 1.4040 0.7555 -0.2280 0.050 Uiso 1 1 calc R . .
H20B H 1.2614 0.7557 -0.3376 0.050 Uiso 1 1 calc R . .
C13 C 0.7472(2) 0.62255(19) -0.51719(17) 0.0415(4) Uani 1 1 d . . .
H13 H 0.7121 0.5264 -0.5744 0.050 Uiso 1 1 calc R . .
C1 C 1.1856(3) 0.7542(2) 0.39765(18) 0.0518(5) Uani 1 1 d . . .
H1A H 1.3155 0.7708 0.4209 0.078 Uiso 1 1 calc R . .
H1B H 1.1261 0.6775 0.4072 0.078 Uiso 1 1 calc R . .
H1C H 1.1568 0.8366 0.4554 0.078 Uiso 1 1 calc R . .
C22 C 1.2970(3) 1.03446(19) -0.2043(2) 0.0537(5) Uani 1 1 d . . .
H22A H 1.3662 1.1307 -0.1712 0.064 Uiso 1 1 calc R . .
H22B H 1.2311 0.9952 -0.2965 0.064 Uiso 1 1 calc R . .
C16 C 0.8472(3) 0.9065(2) -0.3492(2) 0.0514(5) Uani 1 1 d . . .
H16 H 0.8796 1.0026 -0.2928 0.062 Uiso 1 1 calc R . .
C15 C 0.7226(3) 0.8466(3) -0.4707(3) 0.0616(6) Uani 1 1 d . . .
H15 H 0.6724 0.9019 -0.4964 0.074 Uiso 1 1 calc R . .
C14 C 0.6725(3) 0.7046(2) -0.5541(2) 0.0542(5) Uani 1 1 d . . .
H14 H 0.5874 0.6638 -0.6362 0.065 Uiso 1 1 calc R . .
C21 C 1.4262(3) 0.9538(2) -0.1964(2) 0.0541(5) Uani 1 1 d . . .
H21A H 1.5002 0.9976 -0.1055 0.065 Uiso 1 1 calc R . .
H21B H 1.5073 0.9547 -0.2517 0.065 Uiso 1 1 calc R . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O2 C5 1.362(2) . ?
O2 C4 1.3720(19) . ?
C7 C6 1.342(2) . ?
C7 C8 1.451(2) . ?
C7 C11 1.5237(19) . ?
C8 C4 1.3948(19) . ?
C8 C9 1.401(2) . ?
N1 C12 1.386(2) . ?
N1 C11 1.4463(19) . ?
C4 C3 1.382(2) . ?
C6 C5 1.442(2) . ?
C11 C19 1.536(2) . ?
C12 C13 1.398(2) . ?
C12 C17 1.398(2) . ?
C3 C2 1.377(2) . ?
C2 C10 1.397(2) . ?
C2 C1 1.502(2) . ?
C10 C9 1.374(2) . ?
O3 C22 1.431(2) . ?
O3 C18 1.4316(19) . ?
C19 C18 1.523(2) . ?
C19 C20 1.529(2) . ?
O1 C5 1.207(2) . ?
C18 C17 1.511(2) . ?
C17 C16 1.391(2) . ?
C20 C21 1.522(3) . ?
C13 C14 1.373(3) . ?
C22 C21 1.499(3) . ?
C16 C15 1.373(3) . ?
C15 C14 1.372(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
C5 O2 C4 121.40(12) . . ?
C6 C7 C8 118.25(13) . . ?
C6 C7 C11 121.18(13) . . ?
C8 C7 C11 120.56(13) . . ?
C4 C8 C9 116.62(13) . . ?
C4 C8 C7 117.98(13) . . ?
C9 C8 C7 125.39(13) . . ?
C12 N1 C11 120.93(12) . . ?
O2 C4 C3 115.72(13) . . ?
O2 C4 C8 121.83(13) . . ?
C3 C4 C8 122.45(15) . . ?
C7 C6 C5 123.12(14) . . ?
N1 C11 C7 112.47(12) . . ?
N1 C11 C19 108.27(12) . . ?
C7 C11 C19 112.04(12) . . ?
N1 C12 C13 119.91(14) . . ?
N1 C12 C17 120.76(14) . . ?
C13 C12 C17 119.33(15) . . ?
C2 C3 C4 120.12(14) . . ?
C3 C2 C10 118.39(14) . . ?
C3 C2 C1 120.50(15) . . ?
C10 C2 C1 121.10(16) . . ?
C9 C10 C2 121.31(15) . . ?
C10 C9 C8 120.98(14) . . ?
C22 O3 C18 112.87(13) . . ?
C18 C19 C20 110.95(13) . . ?
C18 C19 C11 109.85(13) . . ?
C20 C19 C11 111.42(13) . . ?
O1 C5 O2 117.36(14) . . ?
O1 C5 C6 125.26(16) . . ?
O2 C5 C6 117.37(14) . . ?
O3 C18 C17 112.52(14) . . ?
O3 C18 C19 111.57(14) . . ?
C17 C18 C19 111.58(12) . . ?
C16 C17 C12 118.48(16) . . ?
C16 C17 C18 121.39(15) . . ?
C12 C17 C18 120.10(14) . . ?
C21 C20 C19 110.52(15) . . ?
C14 C13 C12 120.53(17) . . ?
O3 C22 C21 111.81(16) . . ?
C15 C16 C17 121.58(18) . . ?
C14 C15 C16 119.68(18) . . ?
C15 C14 C13 120.39(18) . . ?
C22 C21 C20 110.22(15) . . ?

_diffrn_measured_fraction_theta_max 0.981
_diffrn_reflns_theta_full        25.00
_diffrn_measured_fraction_theta_full 0.994
_refine_diff_density_max         0.409
_refine_diff_density_min         -0.270
_refine_diff_density_rms         0.054
