# 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_sp1
_database_code_depnum_ccdc_archive 'CCDC 940456'
_audit_update_record             
;
2013-11-27 deposited with the CCDC.
2015-02-02 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C28 H24 N2 O3'
_chemical_formula_weight         436.49

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   C2/c

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

_cell_length_a                   20.4475(13)
_cell_length_b                   14.4995(10)
_cell_length_c                   13.9270(9)
_cell_angle_alpha                90.00
_cell_angle_beta                 106.072(2)
_cell_angle_gamma                90.00
_cell_volume                     3967.7(5)
_cell_formula_units_Z            7
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    ?
_cell_measurement_theta_min      ?
_cell_measurement_theta_max      ?

_exptl_crystal_description       needle
_exptl_crystal_colour            yellow
_exptl_crystal_size_max          0.4
_exptl_crystal_size_mid          0.3
_exptl_crystal_size_min          0.2
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.279
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1610
_exptl_absorpt_coefficient_mu    0.084
_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            24613
_diffrn_reflns_av_R_equivalents  0.0387
_diffrn_reflns_av_sigmaI/netI    0.0331
_diffrn_reflns_limit_h_min       -26
_diffrn_reflns_limit_h_max       26
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_theta_min         1.75
_diffrn_reflns_theta_max         27.60
_reflns_number_total             4530
_reflns_number_gt                2909
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    ?
_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)+(0.0571P)²+0.4461P] 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         4530
_refine_ls_number_parameters     350
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0761
_refine_ls_R_factor_gt           0.0438
_refine_ls_wR_factor_ref         0.1182
_refine_ls_wR_factor_gt          0.1043
_refine_ls_goodness_of_fit_ref   1.034
_refine_ls_restrained_S_all      1.034
_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 0.77237(5) 0.36541(7) 0.81889(7) 0.0504(3) Uani 1 1 d . . .
N1 N 0.74891(6) 0.46711(8) 1.03806(8) 0.0430(3) Uani 1 1 d . . .
O1 O 0.73583(7) 0.24200(9) 0.72878(9) 0.0778(4) Uani 1 1 d . . .
O3 O 0.88178(6) 0.51847(8) 0.82636(9) 0.0665(3) Uani 1 1 d . . .
C1 C 0.73324(7) 0.39949(10) 0.96320(9) 0.0418(3) Uani 1 1 d . . .
C15 C 0.79507(7) 0.52592(10) 1.01876(10) 0.0447(3) Uani 1 1 d . . .
C7 C 0.68521(7) 0.27016(10) 0.86037(10) 0.0476(4) Uani 1 1 d . . .
C10 C 0.81148(7) 0.49819(10) 0.93275(10) 0.0450(3) Uani 1 1 d . . .
C2 C 0.68543(7) 0.32466(9) 0.94467(10) 0.0435(3) Uani 1 1 d . . .
C17 C 0.66169(7) 0.51532(10) 1.12400(11) 0.0459(3) Uani 1 1 d . . .
C3 C 0.63944(8) 0.30160(11) 0.99910(12) 0.0525(4) Uani 1 1 d . . .
C9 C 0.77225(7) 0.41823(10) 0.90058(9) 0.0431(3) Uani 1 1 d . . .
C16 C 0.72857(8) 0.46875(12) 1.13070(10) 0.0459(3) Uani 1 1 d . . .
C22 C 0.63799(8) 0.51238(13) 1.20776(13) 0.0597(4) Uani 1 1 d . . .
C11 C 0.86434(8) 0.54360(11) 0.89983(11) 0.0523(4) Uani 1 1 d . . .
C8 C 0.73101(8) 0.28884(11) 0.79791(11) 0.0532(4) Uani 1 1 d . . .
C14 C 0.82422(10) 0.60735(12) 1.08033(12) 0.0577(4) Uani 1 1 d . . .
C6 C 0.64012(9) 0.19612(11) 0.83363(13) 0.0586(4) Uani 1 1 d . . .
C26 C 0.5000 0.85964(17) 0.7500 0.0573(6) Uani 1 2 d S . .
N2 N 0.5000 0.95439(17) 0.7500 0.0874(8) Uani 1 2 d S . .
C18 C 0.62511(9) 0.56278(13) 1.04160(15) 0.0701(5) Uani 1 1 d . . .
C5 C 0.59632(8) 0.22738(12) 0.97185(13) 0.0610(4) Uani 1 1 d . . .
C4 C 0.59631(9) 0.17467(12) 0.88911(14) 0.0648(5) Uani 1 1 d . . .
C25 C 0.54789(9) 0.81094(14) 0.71649(12) 0.0653(5) Uani 1 1 d . . .
C13 C 0.85378(12) 0.67278(13) 1.01781(15) 0.0720(5) Uani 1 1 d . . .
C21 C 0.57967(10) 0.55799(15) 1.21036(18) 0.0785(6) Uani 1 1 d . . .
C12 C 0.89870(11) 0.62338(16) 0.96414(16) 0.0741(5) Uani 1 1 d . . .
C19 C 0.56522(11) 0.60807(16) 1.0444(2) 0.0937(7) Uani 1 1 d . . .
C24 C 0.54719(14) 0.71646(16) 0.71712(16) 0.0903(7) Uani 1 1 d . . .
C20 C 0.54369(11) 0.60538(16) 1.1287(2) 0.0915(7) Uani 1 1 d . . .
C23 C 0.5000 0.6688(3) 0.7500 0.1115(13) Uani 1 2 d S . .
H16B H 0.7665(7) 0.5026(10) 1.1801(11) 0.051(4) Uiso 1 1 d . . .
H16A H 0.7276(7) 0.4057(12) 1.1534(11) 0.055(4) Uiso 1 1 d . . .
H3 H 0.6366(8) 0.3390(11) 1.0569(12) 0.063(4) Uiso 1 1 d . . .
H14B H 0.8589(9) 0.5863(11) 1.1368(13) 0.063(5) Uiso 1 1 d . . .
H4 H 0.5632(8) 0.2118(11) 1.0115(12) 0.065(5) Uiso 1 1 d . . .
H6 H 0.6413(8) 0.1603(12) 0.7756(13) 0.067(5) Uiso 1 1 d . . .
H14A H 0.7903(9) 0.6372(12) 1.1043(13) 0.069(5) Uiso 1 1 d . . .
H5 H 0.5655(9) 0.1195(14) 0.8715(13) 0.087(6) Uiso 1 1 d . . .
H12A H 0.9164(9) 0.6645(13) 0.9220(14) 0.080(5) Uiso 1 1 d . . .
H13B H 0.8789(9) 0.7215(13) 1.0598(14) 0.080(5) Uiso 1 1 d . . .
H18 H 0.6419(8) 0.5627(11) 0.9815(12) 0.063(5) Uiso 1 1 d . . .
H12B H 0.9371(11) 0.5978(15) 1.0129(16) 0.094(7) Uiso 1 1 d . . .
H13A H 0.8151(10) 0.7028(13) 0.9657(15) 0.086(6) Uiso 1 1 d . . .
H22 H 0.6639(9) 0.4758(13) 1.2690(13) 0.081(6) Uiso 1 1 d . . .
H21 H 0.5636(10) 0.5570(14) 1.2713(16) 0.099(7) Uiso 1 1 d . . .
H19 H 0.5437(11) 0.6364(17) 0.9833(18) 0.112(8) Uiso 1 1 d . . .
H20 H 0.5027(12) 0.6389(16) 1.1296(17) 0.116(7) Uiso 1 1 d . . .
H30 H 0.5298(9) 0.9843(13) 0.7255(13) 0.074(5) Uiso 1 1 d . . .
H25 H 0.5824(9) 0.8467(12) 0.6909(13) 0.079(5) Uiso 1 1 d . . .
H24 H 0.5837(13) 0.6843(18) 0.6964(19) 0.126(8) Uiso 1 1 d . . .
H23 H 0.5000 0.606(3) 0.7500 0.138(14) Uiso 1 2 d S . .


_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 C9 1.3720(15) . ?
O2 C8 1.3770(18) . ?
N1 C15 1.3530(17) . ?
N1 C1 1.4021(17) . ?
N1 C16 1.4613(17) . ?
O1 C8 1.2043(17) . ?
O3 C11 1.2283(17) . ?
C1 C9 1.3624(18) . ?
C1 C2 1.435(2) . ?
C15 C10 1.3898(19) . ?
C15 C14 1.484(2) . ?
C7 C6 1.397(2) . ?
C7 C2 1.4142(19) . ?
C7 C8 1.469(2) . ?
C10 C9 1.410(2) . ?
C10 C11 1.444(2) . ?
C2 C3 1.402(2) . ?
C17 C18 1.369(2) . ?
C17 C22 1.382(2) . ?
C17 C16 1.505(2) . ?
C3 C5 1.376(2) . ?
C22 C21 1.373(3) . ?
C11 C12 1.512(3) . ?
C14 C13 1.522(2) . ?
C6 C4 1.371(2) . ?
C26 N2 1.374(3) . ?
C26 C25 1.389(2) 2_656 ?
C26 C25 1.389(2) . ?
C18 C19 1.399(3) . ?
C5 C4 1.383(2) . ?
C25 C24 1.370(3) . ?
C13 C12 1.515(3) . ?
C21 C20 1.358(3) . ?
C19 C20 1.364(3) . ?
C24 C23 1.365(3) . ?
C23 C24 1.365(3) 2_656 ?

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
C9 O2 C8 118.95(11) . . ?
C15 N1 C1 108.75(10) . . ?
C15 N1 C16 123.36(12) . . ?
C1 N1 C16 127.26(12) . . ?
C9 C1 N1 106.42(12) . . ?
C9 C1 C2 121.74(12) . . ?
N1 C1 C2 131.80(12) . . ?
N1 C15 C10 109.70(12) . . ?
N1 C15 C14 125.27(13) . . ?
C10 C15 C14 125.04(13) . . ?
C6 C7 C2 120.06(14) . . ?
C6 C7 C8 117.76(14) . . ?
C2 C7 C8 122.17(13) . . ?
C15 C10 C9 105.06(12) . . ?
C15 C10 C11 121.48(13) . . ?
C9 C10 C11 133.12(13) . . ?
C3 C2 C7 117.85(14) . . ?
C3 C2 C1 127.48(13) . . ?
C7 C2 C1 114.66(12) . . ?
C18 C17 C22 119.02(15) . . ?
C18 C17 C16 123.63(13) . . ?
C22 C17 C16 117.31(14) . . ?
C5 C3 C2 120.79(15) . . ?
C1 C9 O2 123.73(13) . . ?
C1 C9 C10 110.05(12) . . ?
O2 C9 C10 126.22(12) . . ?
N1 C16 C17 115.37(12) . . ?
C21 C22 C17 121.16(19) . . ?
O3 C11 C10 122.99(15) . . ?
O3 C11 C12 121.73(14) . . ?
C10 C11 C12 115.25(14) . . ?
O1 C8 O2 116.29(14) . . ?
O1 C8 C7 125.17(15) . . ?
O2 C8 C7 118.54(12) . . ?
C15 C14 C13 108.97(13) . . ?
C4 C6 C7 120.68(16) . . ?
N2 C26 C25 120.57(12) . 2_656 ?
N2 C26 C25 120.57(12) . . ?
C25 C26 C25 118.9(2) 2_656 . ?
C17 C18 C19 119.47(19) . . ?
C3 C5 C4 120.95(16) . . ?
C6 C4 C5 119.66(16) . . ?
C24 C25 C26 119.8(2) . . ?
C12 C13 C14 112.25(17) . . ?
C20 C21 C22 119.7(2) . . ?
C11 C12 C13 114.09(16) . . ?
C20 C19 C18 120.2(2) . . ?
C23 C24 C25 121.2(2) . . ?
C21 C20 C19 120.4(2) . . ?
C24 C23 C24 119.2(3) . 2_656 ?

_diffrn_measured_fraction_theta_max 0.983
_diffrn_reflns_theta_full        27.60
_diffrn_measured_fraction_theta_full 0.983
_refine_diff_density_max         0.138
_refine_diff_density_min         -0.148
_refine_diff_density_rms         0.031
####################################################################### 
# 
# 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_sp1
_database_code_depnum_ccdc_archive 'CCDC 940457'
_audit_update_record             
;
2013-11-27 deposited with the CCDC.
2015-02-02 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 H16 N O3'
_chemical_formula_weight         342.36

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)/n

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

_cell_length_a                   13.5527(18)
_cell_length_b                   8.7440(12)
_cell_length_c                   14.7881(19)
_cell_angle_alpha                90.00
_cell_angle_beta                 104.612(4)
_cell_angle_gamma                90.00
_cell_volume                     1695.8(4)
_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       needle
_exptl_crystal_colour            yellow
_exptl_crystal_size_max          0.4
_exptl_crystal_size_mid          0.3
_exptl_crystal_size_min          0.2
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.341
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             716
_exptl_absorpt_coefficient_mu    0.090
_exptl_absorpt_correction_type   ?
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_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            20680
_diffrn_reflns_av_R_equivalents  0.0268
_diffrn_reflns_av_sigmaI/netI    0.0219
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_theta_min         1.82
_diffrn_reflns_theta_max         27.67
_reflns_number_total             3875
_reflns_number_gt                3023
_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 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)+(0.1107P)²+1.4747P] 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         3875
_refine_ls_number_parameters     236
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0881
_refine_ls_R_factor_gt           0.0719
_refine_ls_wR_factor_ref         0.2143
_refine_ls_wR_factor_gt          0.2021
_refine_ls_goodness_of_fit_ref   0.975
_refine_ls_restrained_S_all      0.975
_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 0.54409(15) 0.9299(3) 1.13402(14) 0.0652(6) Uani 1 1 d . . .
O2 O 0.49125(12) 0.7847(2) 1.01000(12) 0.0475(4) Uani 1 1 d . . .
O3 O 0.5060(2) 0.7841(3) 0.77889(19) 0.0857(8) Uani 1 1 d . . .
H3 H 0.4914 0.8485 0.8137 0.129 Uiso 1 1 calc R . .
N1 N 0.26719(14) 0.5822(2) 0.90110(13) 0.0435(5) Uani 1 1 d . . .
C1 C 0.47696(18) 0.8482(3) 1.09029(17) 0.0461(5) Uani 1 1 d . . .
C2 C 0.41473(17) 0.6991(3) 0.95451(15) 0.0401(5) Uani 1 1 d . . .
C3 C 0.32378(16) 0.6679(3) 0.97545(15) 0.0399(5) Uani 1 1 d . . .
C4 C 0.16522(17) 0.5200(3) 0.89112(18) 0.0469(6) Uani 1 1 d . . .
H4A H 0.1364 0.4939 0.8261 0.056 Uiso 1 1 calc R . .
H4B H 0.1225 0.5984 0.9080 0.056 Uiso 1 1 calc R . .
C5 C 0.16283(17) 0.3800(3) 0.95033(16) 0.0414(5) Uani 1 1 d . . .
C6 C 0.2483(2) 0.2949(3) 0.9879(2) 0.0598(7) Uani 1 1 d . . .
H6 H 0.3109 0.3246 0.9787 0.072 Uiso 1 1 calc R . .
C7 C 0.2420(3) 0.1652(4) 1.0395(3) 0.0795(10) Uani 1 1 d . . .
H7 H 0.3005 0.1084 1.0650 0.095 Uiso 1 1 calc R . .
C8 C 0.1499(3) 0.1197(4) 1.0533(2) 0.0765(10) Uani 1 1 d . . .
H8 H 0.1459 0.0318 1.0876 0.092 Uiso 1 1 calc R . .
C9 C 0.0648(3) 0.2033(4) 1.0167(2) 0.0677(8) Uani 1 1 d . . .
H9 H 0.0025 0.1728 1.0263 0.081 Uiso 1 1 calc R . .
C10 C 0.0704(2) 0.3330(3) 0.96547(19) 0.0533(6) Uani 1 1 d . . .
H10 H 0.0118 0.3896 0.9407 0.064 Uiso 1 1 calc R . .
C11 C 0.32449(18) 0.5590(3) 0.83808(15) 0.0434(5) Uani 1 1 d . . .
C12 C 0.41735(17) 0.6313(3) 0.86888(15) 0.0423(5) Uani 1 1 d . . .
C13 C 0.49703(19) 0.6350(3) 0.81532(18) 0.0500(6) Uani 1 1 d . . .
H13 H 0.5628 0.6048 0.8565 0.060 Uiso 1 1 calc R . .
C16 C 0.2935(2) 0.4673(3) 0.75066(18) 0.0554(6) Uani 1 1 d . . .
H16A H 0.2904 0.3598 0.7658 0.066 Uiso 1 1 calc R . .
H16B H 0.2265 0.4991 0.7147 0.066 Uiso 1 1 calc R . .
C17 C 0.30495(17) 0.7188(2) 1.06172(16) 0.0406(5) Uani 1 1 d . . .
C18 C 0.2206(2) 0.6844(3) 1.09666(19) 0.0509(6) Uani 1 1 d . . .
H18 H 0.1686 0.6234 1.0617 0.061 Uiso 1 1 calc R . .
C19 C 0.2135(2) 0.7394(3) 1.1819(2) 0.0591(7) Uani 1 1 d . . .
H19 H 0.1567 0.7152 1.2036 0.071 Uiso 1 1 calc R . .
C20 C 0.2897(2) 0.8303(3) 1.2359(2) 0.0596(7) Uani 1 1 d . . .
H20 H 0.2839 0.8676 1.2932 0.071 Uiso 1 1 calc R . .
C21 C 0.3734(2) 0.8648(3) 1.20416(17) 0.0522(6) Uani 1 1 d . . .
H21 H 0.4246 0.9258 1.2403 0.063 Uiso 1 1 calc R . .
C22 C 0.38309(18) 0.8095(3) 1.11817(16) 0.0421(5) Uani 1 1 d . . .
C15 C 0.3696(3) 0.4911(8) 0.6950(3) 0.124(2) Uani 1 1 d . . .
H15A H 0.3701 0.3981 0.6592 0.149 Uiso 1 1 calc R . .
H15B H 0.3426 0.5710 0.6501 0.149 Uiso 1 1 calc R . .
C14 C 0.4698(3) 0.5276(5) 0.7343(3) 0.0880(12) Uani 1 1 d . . .
H14A H 0.4973 0.5700 0.6852 0.106 Uiso 1 1 calc R . .
H14B H 0.5059 0.4326 0.7538 0.106 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
O1 C1 1.208(3) . ?
O2 C1 1.368(3) . ?
O2 C2 1.371(3) . ?
O3 C13 1.427(3) . ?
O3 H3 0.8200 . ?
N1 C11 1.370(3) . ?
N1 C3 1.391(3) . ?
N1 C4 1.458(3) . ?
C1 C22 1.472(3) . ?
C2 C3 1.372(3) . ?
C2 C12 1.407(3) . ?
C3 C17 1.434(3) . ?
C4 C5 1.510(3) . ?
C4 H4A 0.9700 . ?
C4 H4B 0.9700 . ?
C5 C6 1.371(4) . ?
C5 C10 1.389(3) . ?
C6 C7 1.381(4) . ?
C6 H6 0.9300 . ?
C7 C8 1.373(5) . ?
C7 H7 0.9300 . ?
C8 C9 1.358(5) . ?
C8 H8 0.9300 . ?
C9 C10 1.376(4) . ?
C9 H9 0.9300 . ?
C10 H10 0.9300 . ?
C11 C12 1.379(3) . ?
C11 C16 1.489(3) . ?
C12 C13 1.492(3) . ?
C13 C14 1.493(4) . ?
C13 H13 0.9800 . ?
C16 C15 1.488(5) . ?
C16 H16A 0.9700 . ?
C16 H16B 0.9700 . ?
C17 C18 1.401(3) . ?
C17 C22 1.414(3) . ?
C18 C19 1.375(4) . ?
C18 H18 0.9300 . ?
C19 C20 1.386(4) . ?
C19 H19 0.9300 . ?
C20 C21 1.366(4) . ?
C20 H20 0.9300 . ?
C21 C22 1.397(3) . ?
C21 H21 0.9300 . ?
C15 C14 1.374(5) . ?
C15 H15A 0.9700 . ?
C15 H15B 0.9700 . ?
C14 H14A 0.9700 . ?
C14 H14B 0.9700 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C1 O2 C2 119.32(18) . . ?
C13 O3 H3 109.5 . . ?
C11 N1 C3 108.86(18) . . ?
C11 N1 C4 124.2(2) . . ?
C3 N1 C4 126.9(2) . . ?
O1 C1 O2 116.9(2) . . ?
O1 C1 C22 125.0(2) . . ?
O2 C1 C22 118.1(2) . . ?
O2 C2 C3 124.1(2) . . ?
O2 C2 C12 125.6(2) . . ?
C3 C2 C12 110.3(2) . . ?
C2 C3 N1 106.04(19) . . ?
C2 C3 C17 120.7(2) . . ?
N1 C3 C17 133.2(2) . . ?
N1 C4 C5 113.72(19) . . ?
N1 C4 H4A 108.8 . . ?
C5 C4 H4A 108.8 . . ?
N1 C4 H4B 108.8 . . ?
C5 C4 H4B 108.8 . . ?
H4A C4 H4B 107.7 . . ?
C6 C5 C10 118.5(2) . . ?
C6 C5 C4 122.4(2) . . ?
C10 C5 C4 119.1(2) . . ?
C5 C6 C7 120.4(3) . . ?
C5 C6 H6 119.8 . . ?
C7 C6 H6 119.8 . . ?
C8 C7 C6 120.3(3) . . ?
C8 C7 H7 119.8 . . ?
C6 C7 H7 119.8 . . ?
C9 C8 C7 119.8(3) . . ?
C9 C8 H8 120.1 . . ?
C7 C8 H8 120.1 . . ?
C8 C9 C10 120.3(3) . . ?
C8 C9 H9 119.9 . . ?
C10 C9 H9 119.9 . . ?
C9 C10 C5 120.7(3) . . ?
C9 C10 H10 119.7 . . ?
C5 C10 H10 119.7 . . ?
N1 C11 C12 109.5(2) . . ?
N1 C11 C16 125.9(2) . . ?
C12 C11 C16 124.6(2) . . ?
C11 C12 C2 105.2(2) . . ?
C11 C12 C13 123.9(2) . . ?
C2 C12 C13 130.9(2) . . ?
O3 C13 C12 111.2(2) . . ?
O3 C13 C14 107.4(3) . . ?
C12 C13 C14 110.3(2) . . ?
O3 C13 H13 109.3 . . ?
C12 C13 H13 109.3 . . ?
C14 C13 H13 109.3 . . ?
C15 C16 C11 108.8(2) . . ?
C15 C16 H16A 109.9 . . ?
C11 C16 H16A 109.9 . . ?
C15 C16 H16B 109.9 . . ?
C11 C16 H16B 109.9 . . ?
H16A C16 H16B 108.3 . . ?
C18 C17 C22 117.5(2) . . ?
C18 C17 C3 127.3(2) . . ?
C22 C17 C3 115.1(2) . . ?
C19 C18 C17 121.0(3) . . ?
C19 C18 H18 119.5 . . ?
C17 C18 H18 119.5 . . ?
C18 C19 C20 120.9(3) . . ?
C18 C19 H19 119.5 . . ?
C20 C19 H19 119.5 . . ?
C21 C20 C19 119.5(2) . . ?
C21 C20 H20 120.3 . . ?
C19 C20 H20 120.3 . . ?
C20 C21 C22 120.8(3) . . ?
C20 C21 H21 119.6 . . ?
C22 C21 H21 119.6 . . ?
C21 C22 C17 120.2(2) . . ?
C21 C22 C1 117.5(2) . . ?
C17 C22 C1 122.3(2) . . ?
C14 C15 C16 123.2(3) . . ?
C14 C15 H15A 106.5 . . ?
C16 C15 H15A 106.5 . . ?
C14 C15 H15B 106.5 . . ?
C16 C15 H15B 106.5 . . ?
H15A C15 H15B 106.5 . . ?
C15 C14 C13 120.3(3) . . ?
C15 C14 H14A 107.3 . . ?
C13 C14 H14A 107.3 . . ?
C15 C14 H14B 107.3 . . ?
C13 C14 H14B 107.3 . . ?
H14A C14 H14B 106.9 . . ?

_diffrn_measured_fraction_theta_max 0.976
_diffrn_reflns_theta_full        27.67
_diffrn_measured_fraction_theta_full 0.976
_refine_diff_density_max         0.693
_refine_diff_density_min         -0.685
_refine_diff_density_rms         0.053
####################################################################### 
# 
# 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_apd42_0m
_database_code_depnum_ccdc_archive 'CCDC 940458'
_audit_update_record             
;
2013-11-27 deposited with the CCDC.
2015-02-02 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C24 H21 N O4 S'
_chemical_formula_weight         419.48

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'
S S 0.1246 0.1234 '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                   9.8359(7)
_cell_length_b                   9.8990(7)
_cell_length_c                   11.8318(8)
_cell_angle_alpha                98.474(2)
_cell_angle_beta                 91.399(2)
_cell_angle_gamma                112.007(2)
_cell_volume                     1052.42(13)
_cell_formula_units_Z            2
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    ?
_cell_measurement_theta_min      ?
_cell_measurement_theta_max      ?

_exptl_crystal_description       needle
_exptl_crystal_colour            yellow
_exptl_crystal_size_max          0.4
_exptl_crystal_size_mid          0.3
_exptl_crystal_size_min          0.2
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.324
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             440
_exptl_absorpt_coefficient_mu    0.184
_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            10390
_diffrn_reflns_av_R_equivalents  0.0224
_diffrn_reflns_av_sigmaI/netI    0.0245
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_theta_min         1.75
_diffrn_reflns_theta_max         23.33
_reflns_number_total             3023
_reflns_number_gt                2483
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    ?
_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)+(0.1424P)²+1.1653P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constrain
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         3023
_refine_ls_number_parameters     275
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0900
_refine_ls_R_factor_gt           0.0783
_refine_ls_wR_factor_ref         0.2455
_refine_ls_wR_factor_gt          0.2300
_refine_ls_goodness_of_fit_ref   1.051
_refine_ls_restrained_S_all      1.051
_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
S S 0.81469(17) 0.26472(18) 1.04880(12) 0.0961(6) Uani 1 1 d . . .
O2 O 0.6862(3) -0.0055(3) 0.3565(2) 0.0583(7) Uani 1 1 d . . .
O1 O 0.3944(4) -0.2069(3) 0.2185(3) 0.0682(9) Uani 1 1 d . . .
N N 0.5598(4) -0.1906(3) 0.5917(3) 0.0530(8) Uani 1 1 d . . .
O3 O 0.8841(4) 0.1748(4) 0.3211(3) 0.0851(10) Uani 1 1 d . . .
C10 C 0.4689(4) -0.2061(4) 0.4097(3) 0.0474(9) Uani 1 1 d . . .
C16 C 0.5717(4) -0.2228(4) 0.7048(3) 0.0511(9) Uani 1 1 d . . .
C15 C 0.4395(4) -0.2647(4) 0.5121(3) 0.0507(9) Uani 1 1 d . . .
C2 C 0.8119(4) 0.0205(4) 0.5840(3) 0.0514(9) Uani 1 1 d . . .
O4 O 0.8250(5) 0.3348(5) 0.9419(3) 0.1243(17) Uani 1 1 d . . .
C11 C 0.3615(4) -0.2635(4) 0.3166(3) 0.0524(10) Uani 1 1 d . . .
C1 C 0.6668(4) -0.0837(4) 0.5408(3) 0.0485(9) Uani 1 1 d . . .
C7 C 0.8890(4) 0.1097(4) 0.5056(4) 0.0563(10) Uani 1 1 d . . .
C12 C 0.2294(5) -0.3727(4) 0.3301(4) 0.0596(10) Uani 1 1 d . . .
H12 H 0.1563 -0.4106 0.2694 0.072 Uiso 1 1 calc R . .
C8 C 0.8251(5) 0.0989(5) 0.3903(4) 0.0614(11) Uani 1 1 d . . .
C9 C 0.6118(4) -0.0941(4) 0.4322(3) 0.0487(9) Uani 1 1 d . . .
C14 C 0.3055(5) -0.3776(4) 0.5241(4) 0.0596(11) Uani 1 1 d . . .
H14 H 0.2873 -0.4169 0.5915 0.072 Uiso 1 1 calc R . .
C22 C 0.5472(5) -0.1374(4) 0.7972(3) 0.0605(11) Uani 1 1 d . . .
H22 H 0.5165 -0.0615 0.7870 0.073 Uiso 1 1 calc R . .
C21 C 0.5687(5) -0.1652(5) 0.9071(4) 0.0648(11) Uani 1 1 d . . .
H21 H 0.5534 -0.1059 0.9701 0.078 Uiso 1 1 calc R . .
C19 C 0.6118(5) -0.2776(5) 0.9248(3) 0.0616(11) Uani 1 1 d . . .
C13 C 0.2027(5) -0.4274(4) 0.4321(4) 0.0615(11) Uani 1 1 d . . .
H13 H 0.1116 -0.5006 0.4381 0.074 Uiso 1 1 calc R . .
C3 C 0.8831(5) 0.0403(5) 0.6919(4) 0.0673(11) Uani 1 1 d . . .
H3 H 0.8341 -0.0162 0.7456 0.081 Uiso 1 1 calc R . .
C17 C 0.6097(5) -0.3396(5) 0.7199(4) 0.0675(12) Uani 1 1 d . . .
H17 H 0.6223 -0.4008 0.6569 0.081 Uiso 1 1 calc R . .
C18 C 0.6288(6) -0.3652(6) 0.8302(4) 0.0744(13) Uani 1 1 d . . .
H18 H 0.6541 -0.4445 0.8401 0.089 Uiso 1 1 calc R . .
C6 C 1.0328(5) 0.2106(4) 0.5372(5) 0.0690(13) Uani 1 1 d . . .
H6 H 1.0842 0.2683 0.4850 0.083 Uiso 1 1 calc R . .
C4 C 1.0232(5) 0.1407(6) 0.7203(4) 0.0781(14) Uani 1 1 d . . .
H4 H 1.0683 0.1519 0.7929 0.094 Uiso 1 1 calc R . .
C5 C 1.0991(5) 0.2258(5) 0.6428(5) 0.0781(14) Uani 1 1 d . . .
H5 H 1.1952 0.2934 0.6627 0.094 Uiso 1 1 calc R . .
C20 C 0.6370(7) -0.3036(7) 1.0454(4) 0.0942(17) Uani 1 1 d . . .
H20A H 0.6195 -0.2311 1.0999 0.141 Uiso 1 1 calc R . .
H20B H 0.7367 -0.2955 1.0586 0.141 Uiso 1 1 calc R . .
H20C H 0.5707 -0.4007 1.0540 0.141 Uiso 1 1 calc R . .
C029 C 0.8338(7) 0.4069(6) 1.1616(4) 0.0877(15) Uani 1 1 d . . .
H02A H 0.7423 0.4204 1.1669 0.132 Uiso 1 1 calc R . .
H02B H 0.9093 0.4968 1.1480 0.132 Uiso 1 1 calc R . .
H02C H 0.8603 0.3820 1.2321 0.132 Uiso 1 1 calc R . .
C031 C 0.9734(9) 0.2918(12) 1.0592(6) 0.239(8) Uani 1 1 d . . .
H03A H 0.9923 0.2214 1.0035 0.359 Uiso 1 1 calc R . .
H03B H 1.0012 0.2815 1.1348 0.359 Uiso 1 1 calc R . .
H03C H 1.0297 0.3900 1.0460 0.359 Uiso 1 1 calc R . .
H1 H 0.328(6) -0.234(6) 0.163(5) 0.094(18) Uiso 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
S C031 1.480(11) . ?
S O4 1.518(4) . ?
S C029 1.742(6) . ?
O2 C8 1.374(5) . ?
O2 C9 1.375(4) . ?
O1 C11 1.357(5) . ?
N C15 1.384(5) . ?
N C1 1.405(5) . ?
N C16 1.433(5) . ?
O3 C8 1.204(5) . ?
C10 C11 1.400(5) . ?
C10 C15 1.409(5) . ?
C10 C9 1.415(5) . ?
C16 C22 1.364(5) . ?
C16 C17 1.375(6) . ?
C15 C14 1.400(6) . ?
C2 C3 1.392(6) . ?
C2 C7 1.410(5) . ?
C2 C1 1.439(6) . ?
C11 C12 1.375(6) . ?
C1 C9 1.357(5) . ?
C7 C6 1.394(6) . ?
C7 C8 1.460(6) . ?
C12 C13 1.385(6) . ?
C14 C13 1.366(6) . ?
C22 C21 1.396(6) . ?
C21 C19 1.371(6) . ?
C19 C18 1.365(6) . ?
C19 C20 1.517(6) . ?
C3 C4 1.360(7) . ?
C17 C18 1.387(6) . ?
C6 C5 1.356(7) . ?
C4 C5 1.378(7) . ?

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
C031 S O4 93.6(5) . . ?
C031 S C029 93.1(4) . . ?
O4 S C029 104.6(3) . . ?
C8 O2 C9 119.2(3) . . ?
C15 N C1 108.2(3) . . ?
C15 N C16 124.8(3) . . ?
C1 N C16 127.0(3) . . ?
C11 C10 C15 119.1(3) . . ?
C11 C10 C9 135.9(4) . . ?
C15 C10 C9 105.0(3) . . ?
C22 C16 C17 120.1(4) . . ?
C22 C16 N 120.4(3) . . ?
C17 C16 N 119.5(3) . . ?
N C15 C14 129.1(4) . . ?
N C15 C10 108.9(3) . . ?
C14 C15 C10 122.0(4) . . ?
C3 C2 C7 117.8(4) . . ?
C3 C2 C1 127.4(4) . . ?
C7 C2 C1 114.8(4) . . ?
O1 C11 C12 124.0(4) . . ?
O1 C11 C10 117.7(4) . . ?
C12 C11 C10 118.3(4) . . ?
C9 C1 N 107.3(3) . . ?
C9 C1 C2 121.4(3) . . ?
N C1 C2 131.2(3) . . ?
C6 C7 C2 119.5(4) . . ?
C6 C7 C8 117.9(4) . . ?
C2 C7 C8 122.5(4) . . ?
C11 C12 C13 121.4(4) . . ?
O3 C8 O2 116.3(4) . . ?
O3 C8 C7 125.4(4) . . ?
O2 C8 C7 118.3(3) . . ?
C1 C9 O2 123.7(4) . . ?
C1 C9 C10 110.6(3) . . ?
O2 C9 C10 125.7(3) . . ?
C13 C14 C15 116.8(4) . . ?
C16 C22 C21 119.3(4) . . ?
C19 C21 C22 121.7(4) . . ?
C18 C19 C21 117.5(4) . . ?
C18 C19 C20 121.9(4) . . ?
C21 C19 C20 120.6(4) . . ?
C14 C13 C12 122.4(4) . . ?
C4 C3 C2 121.2(5) . . ?
C16 C17 C18 119.1(4) . . ?
C19 C18 C17 122.2(4) . . ?
C5 C6 C7 121.0(5) . . ?
C3 C4 C5 120.9(5) . . ?
C6 C5 C4 119.6(4) . . ?

_diffrn_measured_fraction_theta_max 0.994
_diffrn_reflns_theta_full        23.33
_diffrn_measured_fraction_theta_full 0.994
_refine_diff_density_max         0.862
_refine_diff_density_min         -0.646
_refine_diff_density_rms         0.068
####################################################################### 
# 
# 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_sp1
_database_code_depnum_ccdc_archive 'CCDC 940459'
_audit_update_record             
;
2013-05-21 deposited with the CCDC.
2015-02-02 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 H19 N O4'
_chemical_formula_weight         361.38

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                   9.142(13)
_cell_length_b                   10.310(15)
_cell_length_c                   10.859(16)
_cell_angle_alpha                87.61(3)
_cell_angle_beta                 86.88(3)
_cell_angle_gamma                66.51(2)
_cell_volume                     937(2)
_cell_formula_units_Z            2
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    ?
_cell_measurement_theta_min      ?
_cell_measurement_theta_max      ?

_exptl_crystal_description       needle
_exptl_crystal_colour            yellow
_exptl_crystal_size_max          0.4
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.1
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.281
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             380
_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      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            11889
_diffrn_reflns_av_R_equivalents  0.1620
_diffrn_reflns_av_sigmaI/netI    0.3943
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_theta_min         1.88
_diffrn_reflns_theta_max         29.81
_reflns_number_total             4705
_reflns_number_gt                1579
_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 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)+(0.1202P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         4705
_refine_ls_number_parameters     264
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.2770
_refine_ls_R_factor_gt           0.0888
_refine_ls_wR_factor_ref         0.2803
_refine_ls_wR_factor_gt          0.2224
_refine_ls_goodness_of_fit_ref   0.867
_refine_ls_restrained_S_all      0.867
_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
O1S O 0.8483(5) -0.0833(4) 1.4772(3) 0.0935(12) Uani 1 1 d . . .
O1 O 0.7792(4) -0.2472(3) 1.1486(3) 0.0650(9) Uani 1 1 d . . .
O2 O 0.8330(3) -0.0561(3) 1.1490(2) 0.0490(8) Uani 1 1 d . . .
O2S O 0.7882(5) -0.3065(5) 1.4043(4) 0.1187(16) Uani 1 1 d . . .
O3 O 0.5584(4) 0.6225(3) 0.5561(3) 0.0655(9) Uani 1 1 d . . .
O4 O 0.9909(4) 0.0657(3) 1.3305(3) 0.0604(9) Uani 1 1 d . . .
H4 H 1.0157 0.0884 1.3952 0.091 Uiso 1 1 calc R . .
N1 N 0.7716(4) 0.2422(3) 0.9517(3) 0.0471(9) Uani 1 1 d . . .
C1 C 0.7718(5) -0.1401(5) 1.0915(4) 0.0503(11) Uani 1 1 d . . .
C2 C 0.8241(4) 0.0676(4) 1.0910(3) 0.0436(10) Uani 1 1 d . . .
C3 C 0.7597(5) 0.1142(4) 0.9791(4) 0.0436(10) Uani 1 1 d . . .
C4 C 0.7120(5) 0.3370(4) 0.8484(3) 0.0438(10) Uani 1 1 d . . .
C5 C 0.5509(5) 0.4196(4) 0.8403(4) 0.0562(12) Uani 1 1 d . . .
H5 H 0.4794 0.4107 0.9010 0.067 Uiso 1 1 calc R . .
C6 C 0.4939(5) 0.5162(4) 0.7426(4) 0.0531(11) Uani 1 1 d . . .
H6 H 0.3852 0.5705 0.7370 0.064 Uiso 1 1 calc R . .
C7 C 0.6011(5) 0.5294(4) 0.6550(3) 0.0476(11) Uani 1 1 d . . .
C8 C 0.3919(6) 0.7215(5) 0.5523(5) 0.0806(16) Uani 1 1 d . . .
H8A H 0.3246 0.6699 0.5537 0.121 Uiso 1 1 calc R . .
H8B H 0.3764 0.7786 0.4781 0.121 Uiso 1 1 calc R . .
H8C H 0.3651 0.7813 0.6226 0.121 Uiso 1 1 calc R . .
C9 C 0.8440(5) 0.2740(4) 1.0485(4) 0.0460(10) Uani 1 1 d . . .
C10 C 0.8799(4) 0.1652(4) 1.1383(3) 0.0431(10) Uani 1 1 d . . .
C11 C 0.7064(5) -0.0952(4) 0.9694(4) 0.0466(10) Uani 1 1 d . . .
C12 C 0.6995(5) 0.0303(4) 0.9108(3) 0.0447(10) Uani 1 1 d . . .
C13 C 0.6341(5) 0.0634(5) 0.7937(4) 0.0539(11) Uani 1 1 d . . .
H13 H 0.6282 0.1463 0.7528 0.065 Uiso 1 1 calc R . .
C14 C 0.5785(6) -0.0253(5) 0.7389(4) 0.0676(14) Uani 1 1 d . . .
H14 H 0.5357 -0.0024 0.6612 0.081 Uiso 1 1 calc R . .
C15 C 0.5864(6) -0.1491(5) 0.7998(5) 0.0674(14) Uani 1 1 d . . .
H15 H 0.5484 -0.2085 0.7625 0.081 Uiso 1 1 calc R . .
C16 C 0.6493(5) -0.1848(5) 0.9140(4) 0.0557(12) Uani 1 1 d . . .
H16 H 0.6539 -0.2677 0.9543 0.067 Uiso 1 1 calc R . .
C17 C 0.9544(5) 0.1757(4) 1.2473(4) 0.0472(10) Uani 1 1 d . . .
C18 C 0.9857(5) 0.2926(5) 1.2613(4) 0.0529(11) Uani 1 1 d . . .
H18 H 1.0339 0.3010 1.3320 0.064 Uiso 1 1 calc R . .
C19 C 0.9462(5) 0.4008(4) 1.1704(4) 0.0548(11) Uani 1 1 d . . .
H19 H 0.9675 0.4801 1.1832 0.066 Uiso 1 1 calc R . .
C20 C 0.8766(5) 0.3930(4) 1.0625(4) 0.0501(11) Uani 1 1 d . . .
H20 H 0.8528 0.4642 1.0020 0.060 Uiso 1 1 calc R . .
C21 C 0.8186(5) 0.3499(5) 0.7596(4) 0.0530(11) Uani 1 1 d . . .
H21 H 0.9269 0.2937 0.7644 0.064 Uiso 1 1 calc R . .
C22 C 0.7641(5) 0.4474(5) 0.6626(4) 0.0576(12) Uani 1 1 d . . .
H22 H 0.8361 0.4578 0.6031 0.069 Uiso 1 1 calc R . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O1 C1 1.222(5) . ?
O2 C2 1.374(4) . ?
O2 C1 1.387(5) . ?
O3 C7 1.374(5) . ?
O3 C8 1.458(6) . ?
O4 C17 1.364(5) . ?
O4 H4 0.8200 . ?
N1 C3 1.385(5) . ?
N1 C9 1.388(5) . ?
N1 C4 1.436(5) . ?
C1 C11 1.464(6) . ?
C2 C3 1.363(5) . ?
C2 C10 1.420(6) . ?
C3 C12 1.442(6) . ?
C4 C21 1.374(5) . ?
C4 C5 1.382(6) . ?
C5 C6 1.396(5) . ?
C5 H5 0.9300 . ?
C6 C7 1.371(5) . ?
C6 H6 0.9300 . ?
C7 C22 1.395(6) . ?
C8 H8A 0.9600 . ?
C8 H8B 0.9600 . ?
C8 H8C 0.9600 . ?
C9 C20 1.389(6) . ?
C9 C10 1.403(5) . ?
C10 C17 1.425(6) . ?
C11 C16 1.397(6) . ?
C11 C12 1.399(6) . ?
C12 C13 1.404(6) . ?
C13 C14 1.378(6) . ?
C13 H13 0.9300 . ?
C14 C15 1.391(7) . ?
C14 H14 0.9300 . ?
C15 C16 1.369(6) . ?
C15 H15 0.9300 . ?
C16 H16 0.9300 . ?
C17 C18 1.361(6) . ?
C18 C19 1.405(6) . ?
C18 H18 0.9300 . ?
C19 C20 1.384(6) . ?
C19 H19 0.9300 . ?
C20 H20 0.9300 . ?
C21 C22 1.393(6) . ?
C21 H21 0.9300 . ?
C22 H22 0.9300 . ?

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 O2 C1 118.6(3) . . ?
C7 O3 C8 117.3(4) . . ?
C17 O4 H4 109.5 . . ?
C3 N1 C9 108.3(3) . . ?
C3 N1 C4 128.9(3) . . ?
C9 N1 C4 122.7(3) . . ?
O1 C1 O2 115.8(4) . . ?
O1 C1 C11 125.9(4) . . ?
O2 C1 C11 118.3(4) . . ?
C3 C2 O2 124.5(4) . . ?
C3 C2 C10 110.3(4) . . ?
O2 C2 C10 125.2(3) . . ?
C2 C3 N1 107.6(4) . . ?
C2 C3 C12 120.5(4) . . ?
N1 C3 C12 131.9(4) . . ?
C21 C4 C5 119.9(4) . . ?
C21 C4 N1 118.9(4) . . ?
C5 C4 N1 121.0(3) . . ?
C4 C5 C6 121.0(4) . . ?
C4 C5 H5 119.5 . . ?
C6 C5 H5 119.5 . . ?
C7 C6 C5 118.7(4) . . ?
C7 C6 H6 120.6 . . ?
C5 C6 H6 120.6 . . ?
C6 C7 O3 123.6(4) . . ?
C6 C7 C22 120.8(4) . . ?
O3 C7 C22 115.6(4) . . ?
O3 C8 H8A 109.5 . . ?
O3 C8 H8B 109.5 . . ?
H8A C8 H8B 109.5 . . ?
O3 C8 H8C 109.5 . . ?
H8A C8 H8C 109.5 . . ?
H8B C8 H8C 109.5 . . ?
N1 C9 C20 128.4(4) . . ?
N1 C9 C10 109.2(4) . . ?
C20 C9 C10 122.3(4) . . ?
C9 C10 C2 104.6(4) . . ?
C9 C10 C17 119.1(4) . . ?
C2 C10 C17 136.3(4) . . ?
C16 C11 C12 121.3(4) . . ?
C16 C11 C1 116.2(4) . . ?
C12 C11 C1 122.6(4) . . ?
C11 C12 C13 117.9(4) . . ?
C11 C12 C3 115.6(4) . . ?
C13 C12 C3 126.5(4) . . ?
C14 C13 C12 120.8(4) . . ?
C14 C13 H13 119.6 . . ?
C12 C13 H13 119.6 . . ?
C13 C14 C15 119.9(4) . . ?
C13 C14 H14 120.1 . . ?
C15 C14 H14 120.1 . . ?
C16 C15 C14 120.9(4) . . ?
C16 C15 H15 119.5 . . ?
C14 C15 H15 119.6 . . ?
C15 C16 C11 119.2(4) . . ?
C15 C16 H16 120.4 . . ?
C11 C16 H16 120.4 . . ?
C18 C17 O4 124.4(4) . . ?
C18 C17 C10 118.6(4) . . ?
O4 C17 C10 117.0(4) . . ?
C17 C18 C19 121.0(4) . . ?
C17 C18 H18 119.5 . . ?
C19 C18 H18 119.5 . . ?
C20 C19 C18 122.0(4) . . ?
C20 C19 H19 119.0 . . ?
C18 C19 H19 119.0 . . ?
C19 C20 C9 117.0(4) . . ?
C19 C20 H20 121.5 . . ?
C9 C20 H20 121.5 . . ?
C4 C21 C22 119.9(4) . . ?
C4 C21 H21 120.1 . . ?
C22 C21 H21 120.1 . . ?
C21 C22 C7 119.7(4) . . ?
C21 C22 H22 120.2 . . ?
C7 C22 H22 120.2 . . ?

_diffrn_measured_fraction_theta_max 0.875
_diffrn_reflns_theta_full        29.81
_diffrn_measured_fraction_theta_full 0.875
_refine_diff_density_max         0.433
_refine_diff_density_min         -0.342
_refine_diff_density_rms         0.086
####################################################################### 
# 
# 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_110702bm
_database_code_depnum_ccdc_archive 'CCDC 940478'
_audit_update_record             
;
2013-05-21 deposited with the CCDC.
2015-02-02 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C52 H40 O6'
_chemical_formula_weight         760.84

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'
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                   6.1935(9)
_cell_length_b                   19.541(3)
_cell_length_c                   16.698(3)
_cell_angle_alpha                90.00
_cell_angle_beta                 94.763(3)
_cell_angle_gamma                90.00
_cell_volume                     2014.0(5)
_cell_formula_units_Z            2
_cell_measurement_temperature    298(2)
_cell_measurement_reflns_used    989
_cell_measurement_theta_min      2.42
_cell_measurement_theta_max      20.72

_exptl_crystal_description       block
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.16
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.12
_exptl_crystal_density_meas      1.255
_exptl_crystal_density_diffrn    1.255
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             800
_exptl_absorpt_coefficient_mu    0.081
_exptl_absorpt_correction_type   none
_exptl_absorpt_correction_T_min  0.9871
_exptl_absorpt_correction_T_max  0.9903
_exptl_absorpt_process_details   ?

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      298(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  '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            11695
_diffrn_reflns_av_R_equivalents  0.1159
_diffrn_reflns_av_sigmaI/netI    0.1310
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_k_min       -23
_diffrn_reflns_limit_k_max       21
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_theta_min         2.08
_diffrn_reflns_theta_max         25.01
_reflns_number_total             3548
_reflns_number_gt                1906
_reflns_threshold_expression     >2sigma(I)

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

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

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0523P)²+3.3517P] 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         3548
_refine_ls_number_parameters     262
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.2186
_refine_ls_R_factor_gt           0.1286
_refine_ls_wR_factor_ref         0.2502
_refine_ls_wR_factor_gt          0.2204
_refine_ls_goodness_of_fit_ref   1.129
_refine_ls_restrained_S_all      1.129
_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
C1 C 0.4354(10) 0.3636(3) 0.0318(4) 0.0485(17) Uani 1 1 d . . .
C2 C 0.4649(9) 0.4222(3) 0.0786(3) 0.0400(15) Uani 1 1 d . . .
C3 C 0.6418(9) 0.4273(3) 0.1355(3) 0.0434(16) Uani 1 1 d . . .
H3 H 0.6634 0.4671 0.1657 0.052 Uiso 1 1 calc R . .
C4 C 0.7890(9) 0.3719(3) 0.1476(3) 0.0425(16) Uani 1 1 d . . .
C5 C 0.7500(9) 0.3133(3) 0.1004(4) 0.0441(16) Uani 1 1 d . . .
C6 C 0.5737(9) 0.3095(3) 0.0430(4) 0.0493(18) Uani 1 1 d . . .
H6 H 0.5503 0.2701 0.0124 0.059 Uiso 1 1 calc R . .
C7 C 0.8955(10) 0.2556(3) 0.1128(4) 0.0495(17) Uani 1 1 d . . .
C8 C 1.0105(10) 0.2076(3) 0.1246(4) 0.0469(17) Uani 1 1 d . . .
C9 C 1.1573(9) 0.1514(3) 0.1408(3) 0.0404(15) Uani 1 1 d . . .
C10 C 1.0935(11) 0.0845(3) 0.1301(5) 0.066(2) Uani 1 1 d . . .
H10 H 0.9530 0.0747 0.1093 0.080 Uiso 1 1 calc R . .
C11 C 1.2344(13) 0.0319(3) 0.1499(5) 0.079(2) Uani 1 1 d . . .
H11 H 1.1882 -0.0133 0.1444 0.094 Uiso 1 1 calc R . .
C12 C 1.4422(12) 0.0462(4) 0.1775(4) 0.068(2) Uani 1 1 d . . .
H12 H 1.5394 0.0106 0.1888 0.082 Uiso 1 1 calc R . .
C13 C 1.5091(11) 0.1115(4) 0.1888(4) 0.0595(19) Uani 1 1 d . . .
H13 H 1.6506 0.1205 0.2091 0.071 Uiso 1 1 calc R . .
C14 C 1.3686(10) 0.1645(3) 0.1703(4) 0.0536(18) Uani 1 1 d . . .
H14 H 1.4156 0.2094 0.1777 0.064 Uiso 1 1 calc R . .
C15 C 0.9636(10) 0.3756(3) 0.2080(4) 0.0496(17) Uani 1 1 d . . .
C16 C 1.1073(10) 0.3738(3) 0.2589(4) 0.0503(18) Uani 1 1 d . . .
C17 C 1.2802(9) 0.3690(3) 0.3221(4) 0.0421(16) Uani 1 1 d . . .
C18 C 1.2655(11) 0.3956(4) 0.3977(4) 0.064(2) Uani 1 1 d . . .
H18 H 1.1397 0.4182 0.4094 0.077 Uiso 1 1 calc R . .
C19 C 1.4333(15) 0.3894(4) 0.4559(4) 0.084(3) Uani 1 1 d . . .
H19 H 1.4211 0.4073 0.5069 0.101 Uiso 1 1 calc R . .
C20 C 1.6209(13) 0.3564(5) 0.4384(5) 0.083(3) Uani 1 1 d . . .
H20 H 1.7356 0.3520 0.4777 0.099 Uiso 1 1 calc R . .
C21 C 1.6373(11) 0.3309(4) 0.3655(5) 0.076(2) Uani 1 1 d . . .
H21 H 1.7655 0.3097 0.3541 0.092 Uiso 1 1 calc R . .
C22 C 1.4722(10) 0.3351(3) 0.3072(4) 0.0559(18) Uani 1 1 d . . .
H22 H 1.4862 0.3154 0.2572 0.067 Uiso 1 1 calc R . .
C23 C 0.2122(11) 0.3119(3) -0.0771(4) 0.062(2) Uani 1 1 d . . .
H23A H 0.1473 0.2750 -0.0486 0.074 Uiso 1 1 calc R . .
H23B H 0.3423 0.2947 -0.0987 0.074 Uiso 1 1 calc R . .
C24 C 0.0590(11) 0.3371(4) -0.1424(4) 0.074(2) Uani 1 1 d . . .
H24A H 0.1378 0.3693 -0.1733 0.089 Uiso 1 1 calc R . .
H24B H 0.0227 0.2984 -0.1774 0.089 Uiso 1 1 calc R . .
C25 C -0.1204(9) 0.4305(3) -0.0865(4) 0.0515(18) Uani 1 1 d . . .
H25A H 0.0078 0.4560 -0.0979 0.062 Uiso 1 1 calc R . .
H25B H -0.1154 0.4226 -0.0290 0.062 Uiso 1 1 calc R . .
C26 C 0.3184(9) 0.5307(3) 0.1140(4) 0.0499(18) Uani 1 1 d . . .
H26A H 0.4469 0.5582 0.1088 0.060 Uiso 1 1 calc R . .
H26B H 0.3148 0.5171 0.1697 0.060 Uiso 1 1 calc R . .
O1 O 0.2641(7) 0.3673(2) -0.0243(3) 0.0672(15) Uani 1 1 d . . .
O2 O -0.1277(7) 0.3672(2) -0.1282(3) 0.0761(16) Uani 1 1 d . . .
O3 O 0.3171(6) 0.4725(2) 0.0632(2) 0.0524(12) Uani 1 1 d . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C1 O1 1.357(6) . ?
C1 C6 1.363(7) . ?
C1 C2 1.391(8) . ?
C2 O3 1.352(6) . ?
C2 C3 1.393(7) . ?
C3 C4 1.419(7) . ?
C3 H3 0.9300 . ?
C4 C5 1.400(8) . ?
C4 C15 1.417(8) . ?
C5 C6 1.393(7) . ?
C5 C7 1.448(8) . ?
C6 H6 0.9300 . ?
C7 C8 1.184(7) . ?
C8 C9 1.437(8) . ?
C9 C10 1.374(8) . ?
C9 C14 1.384(8) . ?
C10 C11 1.371(9) . ?
C10 H10 0.9300 . ?
C11 C12 1.360(9) . ?
C11 H11 0.9300 . ?
C12 C13 1.349(9) . ?
C12 H12 0.9300 . ?
C13 C14 1.372(8) . ?
C13 H13 0.9300 . ?
C14 H14 0.9300 . ?
C15 C16 1.180(8) . ?
C16 C17 1.442(8) . ?
C17 C18 1.375(9) . ?
C17 C22 1.401(8) . ?
C18 C19 1.368(9) . ?
C18 H18 0.9300 . ?
C19 C20 1.381(11) . ?
C19 H19 0.9300 . ?
C20 C21 1.327(11) . ?
C20 H20 0.9300 . ?
C21 C22 1.354(9) . ?
C21 H21 0.9300 . ?
C22 H22 0.9300 . ?
C23 O1 1.415(6) . ?
C23 C24 1.470(8) . ?
C23 H23A 0.9700 . ?
C23 H23B 0.9700 . ?
C24 O2 1.336(7) . ?
C24 H24A 0.9700 . ?
C24 H24B 0.9700 . ?
C25 O2 1.417(6) . ?
C25 C26 1.482(7) 3_565 ?
C25 H25A 0.9700 . ?
C25 H25B 0.9700 . ?
C26 O3 1.420(6) . ?
C26 C25 1.482(7) 3_565 ?
C26 H26A 0.9700 . ?
C26 H26B 0.9700 . ?

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
O1 C1 C6 125.6(6) . . ?
O1 C1 C2 113.8(5) . . ?
C6 C1 C2 120.6(5) . . ?
O3 C2 C1 115.8(5) . . ?
O3 C2 C3 124.1(5) . . ?
C1 C2 C3 120.1(5) . . ?
C2 C3 C4 120.2(5) . . ?
C2 C3 H3 119.9 . . ?
C4 C3 H3 119.9 . . ?
C5 C4 C15 121.9(5) . . ?
C5 C4 C3 117.7(5) . . ?
C15 C4 C3 120.4(5) . . ?
C6 C5 C4 121.3(5) . . ?
C6 C5 C7 120.0(5) . . ?
C4 C5 C7 118.7(5) . . ?
C1 C6 C5 120.1(6) . . ?
C1 C6 H6 120.0 . . ?
C5 C6 H6 120.0 . . ?
C8 C7 C5 178.1(7) . . ?
C7 C8 C9 177.3(7) . . ?
C10 C9 C14 118.4(5) . . ?
C10 C9 C8 122.2(5) . . ?
C14 C9 C8 119.4(6) . . ?
C11 C10 C9 120.8(6) . . ?
C11 C10 H10 119.6 . . ?
C9 C10 H10 119.6 . . ?
C12 C11 C10 119.5(7) . . ?
C12 C11 H11 120.2 . . ?
C10 C11 H11 120.2 . . ?
C13 C12 C11 120.9(6) . . ?
C13 C12 H12 119.6 . . ?
C11 C12 H12 119.6 . . ?
C12 C13 C14 120.1(6) . . ?
C12 C13 H13 120.0 . . ?
C14 C13 H13 120.0 . . ?
C13 C14 C9 120.3(6) . . ?
C13 C14 H14 119.9 . . ?
C9 C14 H14 119.9 . . ?
C16 C15 C4 175.3(7) . . ?
C15 C16 C17 177.8(7) . . ?
C18 C17 C22 117.6(6) . . ?
C18 C17 C16 123.0(6) . . ?
C22 C17 C16 119.4(6) . . ?
C19 C18 C17 121.0(7) . . ?
C19 C18 H18 119.5 . . ?
C17 C18 H18 119.5 . . ?
C18 C19 C20 119.6(8) . . ?
C18 C19 H19 120.2 . . ?
C20 C19 H19 120.2 . . ?
C21 C20 C19 119.9(7) . . ?
C21 C20 H20 120.0 . . ?
C19 C20 H20 120.0 . . ?
C20 C21 C22 121.8(8) . . ?
C20 C21 H21 119.1 . . ?
C22 C21 H21 119.1 . . ?
C21 C22 C17 120.1(7) . . ?
C21 C22 H22 119.9 . . ?
C17 C22 H22 119.9 . . ?
O1 C23 C24 107.8(5) . . ?
O1 C23 H23A 110.1 . . ?
C24 C23 H23A 110.1 . . ?
O1 C23 H23B 110.1 . . ?
C24 C23 H23B 110.1 . . ?
H23A C23 H23B 108.5 . . ?
O2 C24 C23 122.1(7) . . ?
O2 C24 H24A 106.8 . . ?
C23 C24 H24A 106.8 . . ?
O2 C24 H24B 106.8 . . ?
C23 C24 H24B 106.8 . . ?
H24A C24 H24B 106.7 . . ?
O2 C25 C26 107.6(4) . 3_565 ?
O2 C25 H25A 110.2 . . ?
C26 C25 H25A 110.2 3_565 . ?
O2 C25 H25B 110.2 . . ?
C26 C25 H25B 110.2 3_565 . ?
H25A C25 H25B 108.5 . . ?
O3 C26 C25 105.2(4) . 3_565 ?
O3 C26 H26A 110.7 . . ?
C25 C26 H26A 110.7 3_565 . ?
O3 C26 H26B 110.7 . . ?
C25 C26 H26B 110.7 3_565 . ?
H26A C26 H26B 108.8 . . ?
C1 O1 C23 120.9(5) . . ?
C24 O2 C25 118.6(5) . . ?
C2 O3 C26 119.9(4) . . ?

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
O1 C1 C2 O3 1.9(8) . . . . ?
C6 C1 C2 O3 -179.2(6) . . . . ?
O1 C1 C2 C3 -176.3(6) . . . . ?
C6 C1 C2 C3 2.5(10) . . . . ?
O3 C2 C3 C4 -179.9(6) . . . . ?
C1 C2 C3 C4 -1.8(9) . . . . ?
C2 C3 C4 C5 0.4(9) . . . . ?
C2 C3 C4 C15 -177.1(6) . . . . ?
C15 C4 C5 C6 177.8(6) . . . . ?
C3 C4 C5 C6 0.4(9) . . . . ?
C15 C4 C5 C7 -1.3(9) . . . . ?
C3 C4 C5 C7 -178.7(6) . . . . ?
O1 C1 C6 C5 177.0(6) . . . . ?
C2 C1 C6 C5 -1.7(10) . . . . ?
C4 C5 C6 C1 0.2(10) . . . . ?
C7 C5 C6 C1 179.4(6) . . . . ?
C6 C5 C7 C8 -86(21) . . . . ?
C4 C5 C7 C8 93(21) . . . . ?
C5 C7 C8 C9 -110(23) . . . . ?
C7 C8 C9 C10 166(16) . . . . ?
C7 C8 C9 C14 -12(16) . . . . ?
C14 C9 C10 C11 1.4(11) . . . . ?
C8 C9 C10 C11 -176.8(7) . . . . ?
C9 C10 C11 C12 -2.5(12) . . . . ?
C10 C11 C12 C13 2.7(12) . . . . ?
C11 C12 C13 C14 -1.7(12) . . . . ?
C12 C13 C14 C9 0.6(11) . . . . ?
C10 C9 C14 C13 -0.4(10) . . . . ?
C8 C9 C14 C13 177.8(6) . . . . ?
C5 C4 C15 C16 -30(9) . . . . ?
C3 C4 C15 C16 147(9) . . . . ?
C4 C15 C16 C17 -16(26) . . . . ?
C15 C16 C17 C18 -95(20) . . . . ?
C15 C16 C17 C22 85(20) . . . . ?
C22 C17 C18 C19 0.3(10) . . . . ?
C16 C17 C18 C19 179.5(6) . . . . ?
C17 C18 C19 C20 0.5(11) . . . . ?
C18 C19 C20 C21 0.0(12) . . . . ?
C19 C20 C21 C22 -1.4(12) . . . . ?
C20 C21 C22 C17 2.2(11) . . . . ?
C18 C17 C22 C21 -1.7(9) . . . . ?
C16 C17 C22 C21 179.1(6) . . . . ?
O1 C23 C24 O2 -55.7(9) . . . . ?
C6 C1 O1 C23 1.0(10) . . . . ?
C2 C1 O1 C23 179.8(6) . . . . ?
C24 C23 O1 C1 -165.8(6) . . . . ?
C23 C24 O2 C25 64.6(9) . . . . ?
C26 C25 O2 C24 151.0(6) 3_565 . . . ?
C1 C2 O3 C26 172.5(6) . . . . ?
C3 C2 O3 C26 -9.3(9) . . . . ?
C25 C26 O3 C2 -172.5(5) 3_565 . . . ?

_diffrn_measured_fraction_theta_max 0.996
_diffrn_reflns_theta_full        25.01
_diffrn_measured_fraction_theta_full 0.996
_refine_diff_density_max         0.330
_refine_diff_density_min         -0.239
_refine_diff_density_rms         0.055
