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

####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_shelxl
_audit_block_doi                 10.5517/cctn6yl
_database_code_depnum_ccdc_archive 'CCDC 764210'
loop_
_citation_id
_citation_doi
_citation_year
1 10.1055/s-0031-1289704 2012
_audit_update_record             
;
2010-02-01 deposited with the CCDC.
2014-12-22 downloaded from the CCDC.
;
#TrackingRef 'DK-IV-32.cif'


_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C26 H22 N2 O3'
_chemical_formula_weight         410.46

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           triclinic
_symmetry_space_group_name_H-M   P-1

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

_cell_length_a                   8.9280(4)
_cell_length_b                   10.0923(4)
_cell_length_c                   11.9044(5)
_cell_angle_alpha                95.0270(10)
_cell_angle_beta                 93.1720(10)
_cell_angle_gamma                98.991(2)
_cell_volume                     1052.78(8)
_cell_formula_units_Z            2
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    8834
_cell_measurement_theta_min      2.05
_cell_measurement_theta_max      31.20

_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.25
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.20
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.295
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             432
_exptl_absorpt_coefficient_mu    0.085
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.9790
_exptl_absorpt_correction_T_max  0.9831
_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_%        0
_diffrn_reflns_number            28847
_diffrn_reflns_av_R_equivalents  0.0277
_diffrn_reflns_av_sigmaI/netI    0.0286
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_theta_min         2.05
_diffrn_reflns_theta_max         32.28
_reflns_number_total             7433
_reflns_number_gt                4947
_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    'SIR92 (Altornare et al., 1993)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    
'ORTEP3 (Farrugia, 1997) and Mercury (Bruno et al., 2002)'
_computing_publication_material  'SHELXL-97 (Sheldrick, 1997)'

_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)+(0.0895P)²+0.2365P] 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         7433
_refine_ls_number_parameters     289
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0948
_refine_ls_R_factor_gt           0.0626
_refine_ls_wR_factor_ref         0.1904
_refine_ls_wR_factor_gt          0.1658
_refine_ls_goodness_of_fit_ref   1.049
_refine_ls_restrained_S_all      1.049
_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 0.18688(14) 0.30903(14) 0.18304(10) 0.0327(3) Uani 1 1 d . . .
C2 C 0.09250(16) 0.38274(17) 0.10248(12) 0.0418(3) Uani 1 1 d . . .
C3 C 0.31829(16) 0.52072(17) 0.14566(12) 0.0419(3) Uani 1 1 d . . .
C4 C 0.4325(2) 0.6297(2) 0.14951(17) 0.0582(5) Uani 1 1 d . . .
H4 H 0.4204 0.7049 0.1122 0.070 Uiso 1 1 calc R . .
C5 C 0.5666(2) 0.6226(2) 0.21141(18) 0.0635(5) Uani 1 1 d . . .
H5 H 0.6454 0.6955 0.2173 0.076 Uiso 1 1 calc R . .
C6 C 0.58552(19) 0.5102(2) 0.26430(17) 0.0587(5) Uani 1 1 d . . .
H6 H 0.6775 0.5074 0.3040 0.070 Uiso 1 1 calc R . .
C7 C 0.46918(17) 0.40086(17) 0.25926(13) 0.0452(3) Uani 1 1 d . . .
H7 H 0.4828 0.3241 0.2940 0.054 Uiso 1 1 calc R . .
C8 C 0.33290(15) 0.40837(15) 0.20164(11) 0.0351(3) Uani 1 1 d . . .
C9 C 0.09670(14) 0.27119(13) 0.28914(10) 0.0317(3) Uani 1 1 d . . .
C10 C 0.21315(19) 0.27681(17) 0.39002(12) 0.0461(4) Uani 1 1 d . . .
C11 C 0.2129(2) 0.51265(18) 0.42028(13) 0.0525(4) Uani 1 1 d . . .
C12 C 0.3071(3) 0.6340(2) 0.45399(17) 0.0697(6) Uani 1 1 d . . .
H12 H 0.3998 0.6361 0.4943 0.084 Uiso 1 1 calc R . .
C13 C 0.2604(3) 0.7499(2) 0.4267(2) 0.0862(8) Uani 1 1 d . . .
H13 H 0.3221 0.8322 0.4486 0.103 Uiso 1 1 calc R . .
C14 C 0.1256(3) 0.7471(2) 0.3680(3) 0.0917(9) Uani 1 1 d . . .
H14 H 0.0953 0.8274 0.3507 0.110 Uiso 1 1 calc R . .
C15 C 0.0312(2) 0.62413(19) 0.3332(2) 0.0744(7) Uani 1 1 d . . .
H15 H -0.0610 0.6228 0.2923 0.089 Uiso 1 1 calc R . .
C16 C 0.0758(2) 0.50551(16) 0.35981(15) 0.0513(4) Uani 1 1 d . . .
C17 C -0.01337(17) 0.36729(14) 0.32385(14) 0.0421(3) Uani 1 1 d . . .
H17A H -0.0853 0.3718 0.2607 0.051 Uiso 1 1 calc R . .
H17B H -0.0699 0.3344 0.3858 0.051 Uiso 1 1 calc R . .
C18 C 0.02149(16) 0.12015(14) 0.25787(12) 0.0367(3) Uani 1 1 d . . .
C19 C -0.14732(17) 0.08374(14) 0.26735(12) 0.0383(3) Uani 1 1 d . . .
C20 C -0.2008(2) 0.00358(17) 0.34999(15) 0.0493(4) Uani 1 1 d . . .
H20 H -0.1316 -0.0238 0.4008 0.059 Uiso 1 1 calc R . .
C21 C -0.3542(2) -0.0364(2) 0.35854(19) 0.0636(5) Uani 1 1 d . . .
H21 H -0.3876 -0.0909 0.4142 0.076 Uiso 1 1 calc R . .
C22 C -0.4578(2) 0.0044(2) 0.2848(2) 0.0648(5) Uani 1 1 d . . .
H22 H -0.5615 -0.0213 0.2909 0.078 Uiso 1 1 calc R . .
C23 C -0.4073(2) 0.08315(19) 0.20232(18) 0.0577(4) Uani 1 1 d . . .
H23 H -0.4772 0.1106 0.1522 0.069 Uiso 1 1 calc R . .
C24 C -0.25367(19) 0.12229(17) 0.19277(14) 0.0484(4) Uani 1 1 d . . .
H24 H -0.2212 0.1750 0.1358 0.058 Uiso 1 1 calc R . .
C25 C 0.07155(18) 0.08433(17) 0.14028(14) 0.0472(4) Uani 1 1 d . . .
H25A H 0.0900 -0.0081 0.1317 0.057 Uiso 1 1 calc R . .
H25B H -0.0051 0.0957 0.0825 0.057 Uiso 1 1 calc R . .
C26 C 0.2647(2) 0.1770(2) 0.01946(15) 0.0658(5) Uani 1 1 d . . .
H26A H 0.2859 0.0889 -0.0045 0.099 Uiso 1 1 calc R . .
H26B H 0.3558 0.2419 0.0201 0.099 Uiso 1 1 calc R . .
H26C H 0.1881 0.1996 -0.0319 0.099 Uiso 1 1 calc R . .
N1 N 0.21084(14) 0.17778(14) 0.13261(10) 0.0428(3) Uani 1 1 d . . .
N2 N 0.17482(15) 0.50215(16) 0.08736(12) 0.0505(4) Uani 1 1 d . . .
O1 O -0.03426(13) 0.33760(14) 0.05740(10) 0.0572(3) Uani 1 1 d . . .
O2 O 0.26613(17) 0.18314(15) 0.41917(12) 0.0730(4) Uani 1 1 d . . .
O3 O 0.26132(16) 0.39709(13) 0.45070(9) 0.0581(3) Uani 1 1 d . . .
H18 H 0.073(2) 0.0690(19) 0.3078(16) 0.053(5) Uiso 1 1 d . . .
H2 H 0.141(3) 0.561(3) 0.043(2) 0.082(7) 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
C1 N1 1.4576(19) . ?
C1 C8 1.5081(19) . ?
C1 C2 1.5538(18) . ?
C1 C9 1.5780(17) . ?
C2 O1 1.2269(17) . ?
C2 N2 1.342(2) . ?
C3 C4 1.374(2) . ?
C3 C8 1.384(2) . ?
C3 N2 1.4004(18) . ?
C4 C5 1.385(3) . ?
C4 H4 0.9300 . ?
C5 C6 1.373(3) . ?
C5 H5 0.9300 . ?
C6 C7 1.387(2) . ?
C6 H6 0.9300 . ?
C7 C8 1.3791(18) . ?
C7 H7 0.9300 . ?
C9 C17 1.5329(19) . ?
C9 C10 1.5355(18) . ?
C9 C18 1.5703(19) . ?
C10 O2 1.190(2) . ?
C10 O3 1.352(2) . ?
C11 C16 1.374(3) . ?
C11 O3 1.376(2) . ?
C11 C12 1.386(3) . ?
C12 C13 1.361(4) . ?
C12 H12 0.9300 . ?
C13 C14 1.352(4) . ?
C13 H13 0.9300 . ?
C14 C15 1.403(3) . ?
C14 H14 0.9300 . ?
C15 C16 1.376(3) . ?
C15 H15 0.9300 . ?
C16 C17 1.508(2) . ?
C17 H17A 0.9700 . ?
C17 H17B 0.9700 . ?
C18 C19 1.507(2) . ?
C18 C25 1.524(2) . ?
C18 H18 0.963(19) . ?
C19 C20 1.386(2) . ?
C19 C24 1.387(2) . ?
C20 C21 1.378(3) . ?
C20 H20 0.9300 . ?
C21 C22 1.374(3) . ?
C21 H21 0.9300 . ?
C22 C23 1.369(3) . ?
C22 H22 0.9300 . ?
C23 C24 1.381(2) . ?
C23 H23 0.9300 . ?
C24 H24 0.9300 . ?
C25 N1 1.451(2) . ?
C25 H25A 0.9700 . ?
C25 H25B 0.9700 . ?
C26 N1 1.455(2) . ?
C26 H26A 0.9600 . ?
C26 H26B 0.9600 . ?
C26 H26C 0.9600 . ?
N2 H2 0.90(2) . ?

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
N1 C1 C8 112.08(11) . . ?
N1 C1 C2 112.81(11) . . ?
C8 C1 C2 100.71(11) . . ?
N1 C1 C9 102.40(10) . . ?
C8 C1 C9 118.45(10) . . ?
C2 C1 C9 110.83(10) . . ?
O1 C2 N2 125.61(13) . . ?
O1 C2 C1 125.71(13) . . ?
N2 C2 C1 108.65(11) . . ?
C4 C3 C8 122.53(14) . . ?
C4 C3 N2 128.00(15) . . ?
C8 C3 N2 109.47(13) . . ?
C3 C4 C5 117.08(17) . . ?
C3 C4 H4 121.5 . . ?
C5 C4 H4 121.5 . . ?
C6 C5 C4 121.37(17) . . ?
C6 C5 H5 119.3 . . ?
C4 C5 H5 119.3 . . ?
C5 C6 C7 120.81(16) . . ?
C5 C6 H6 119.6 . . ?
C7 C6 H6 119.6 . . ?
C8 C7 C6 118.55(15) . . ?
C8 C7 H7 120.7 . . ?
C6 C7 H7 120.7 . . ?
C7 C8 C3 119.56(13) . . ?
C7 C8 C1 130.97(13) . . ?
C3 C8 C1 109.44(11) . . ?
C17 C9 C10 106.84(12) . . ?
C17 C9 C18 115.14(11) . . ?
C10 C9 C18 108.11(11) . . ?
C17 C9 C1 114.41(10) . . ?
C10 C9 C1 107.83(11) . . ?
C18 C9 C1 104.19(10) . . ?
O2 C10 O3 116.72(14) . . ?
O2 C10 C9 125.09(15) . . ?
O3 C10 C9 118.19(14) . . ?
C16 C11 O3 120.30(15) . . ?
C16 C11 C12 122.4(2) . . ?
O3 C11 C12 117.26(19) . . ?
C13 C12 C11 118.4(2) . . ?
C13 C12 H12 120.8 . . ?
C11 C12 H12 120.8 . . ?
C14 C13 C12 121.0(2) . . ?
C14 C13 H13 119.5 . . ?
C12 C13 H13 119.5 . . ?
C13 C14 C15 120.6(2) . . ?
C13 C14 H14 119.7 . . ?
C15 C14 H14 119.7 . . ?
C16 C15 C14 119.6(2) . . ?
C16 C15 H15 120.2 . . ?
C14 C15 H15 120.2 . . ?
C11 C16 C15 118.10(18) . . ?
C11 C16 C17 117.49(15) . . ?
C15 C16 C17 124.38(19) . . ?
C16 C17 C9 109.17(12) . . ?
C16 C17 H17A 109.8 . . ?
C9 C17 H17A 109.8 . . ?
C16 C17 H17B 109.8 . . ?
C9 C17 H17B 109.8 . . ?
H17A C17 H17B 108.3 . . ?
C19 C18 C25 113.59(12) . . ?
C19 C18 C9 117.93(11) . . ?
C25 C18 C9 104.50(11) . . ?
C19 C18 H18 108.4(11) . . ?
C25 C18 H18 105.9(11) . . ?
C9 C18 H18 105.6(11) . . ?
C20 C19 C24 117.72(15) . . ?
C20 C19 C18 119.68(13) . . ?
C24 C19 C18 122.54(13) . . ?
C21 C20 C19 121.44(16) . . ?
C21 C20 H20 119.3 . . ?
C19 C20 H20 119.3 . . ?
C22 C21 C20 119.96(17) . . ?
C22 C21 H21 120.0 . . ?
C20 C21 H21 120.0 . . ?
C23 C22 C21 119.50(17) . . ?
C23 C22 H22 120.2 . . ?
C21 C22 H22 120.2 . . ?
C22 C23 C24 120.71(17) . . ?
C22 C23 H23 119.6 . . ?
C24 C23 H23 119.6 . . ?
C23 C24 C19 120.66(16) . . ?
C23 C24 H24 119.7 . . ?
C19 C24 H24 119.7 . . ?
N1 C25 C18 104.63(12) . . ?
N1 C25 H25A 110.8 . . ?
C18 C25 H25A 110.8 . . ?
N1 C25 H25B 110.8 . . ?
C18 C25 H25B 110.8 . . ?
H25A C25 H25B 108.9 . . ?
N1 C26 H26A 109.5 . . ?
N1 C26 H26B 109.5 . . ?
H26A C26 H26B 109.5 . . ?
N1 C26 H26C 109.5 . . ?
H26A C26 H26C 109.5 . . ?
H26B C26 H26C 109.5 . . ?
C25 N1 C26 113.77(13) . . ?
C25 N1 C1 107.07(11) . . ?
C26 N1 C1 115.04(14) . . ?
C2 N2 C3 111.66(12) . . ?
C2 N2 H2 123.0(16) . . ?
C3 N2 H2 125.4(16) . . ?
C10 O3 C11 121.15(13) . . ?

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
N1 C1 C2 O1 55.8(2) . . . . ?
C8 C1 C2 O1 175.48(16) . . . . ?
C9 C1 C2 O1 -58.3(2) . . . . ?
N1 C1 C2 N2 -122.10(15) . . . . ?
C8 C1 C2 N2 -2.45(16) . . . . ?
C9 C1 C2 N2 123.75(14) . . . . ?
C8 C3 C4 C5 0.8(3) . . . . ?
N2 C3 C4 C5 -178.43(18) . . . . ?
C3 C4 C5 C6 1.5(3) . . . . ?
C4 C5 C6 C7 -1.4(3) . . . . ?
C5 C6 C7 C8 -1.2(3) . . . . ?
C6 C7 C8 C3 3.4(2) . . . . ?
C6 C7 C8 C1 -178.90(15) . . . . ?
C4 C3 C8 C7 -3.3(2) . . . . ?
N2 C3 C8 C7 176.04(14) . . . . ?
C4 C3 C8 C1 178.51(16) . . . . ?
N2 C3 C8 C1 -2.10(17) . . . . ?
N1 C1 C8 C7 -55.00(19) . . . . ?
C2 C1 C8 C7 -175.16(15) . . . . ?
C9 C1 C8 C7 63.9(2) . . . . ?
N1 C1 C8 C3 122.86(13) . . . . ?
C2 C1 C8 C3 2.69(14) . . . . ?
C9 C1 C8 C3 -118.24(13) . . . . ?
N1 C1 C9 C17 -149.91(11) . . . . ?
C8 C1 C9 C17 86.25(14) . . . . ?
C2 C1 C9 C17 -29.36(16) . . . . ?
N1 C1 C9 C10 91.39(12) . . . . ?
C8 C1 C9 C10 -32.45(16) . . . . ?
C2 C1 C9 C10 -148.06(12) . . . . ?
N1 C1 C9 C18 -23.33(12) . . . . ?
C8 C1 C9 C18 -147.17(12) . . . . ?
C2 C1 C9 C18 97.22(12) . . . . ?
C17 C9 C10 O2 142.82(18) . . . . ?
C18 C9 C10 O2 18.3(2) . . . . ?
C1 C9 C10 O2 -93.76(19) . . . . ?
C17 C9 C10 O3 -37.78(17) . . . . ?
C18 C9 C10 O3 -162.25(13) . . . . ?
C1 C9 C10 O3 85.65(16) . . . . ?
C16 C11 C12 C13 0.6(3) . . . . ?
O3 C11 C12 C13 -178.83(17) . . . . ?
C11 C12 C13 C14 0.0(3) . . . . ?
C12 C13 C14 C15 -0.5(4) . . . . ?
C13 C14 C15 C16 0.6(4) . . . . ?
O3 C11 C16 C15 178.85(16) . . . . ?
C12 C11 C16 C15 -0.6(3) . . . . ?
O3 C11 C16 C17 -3.1(2) . . . . ?
C12 C11 C16 C17 177.50(15) . . . . ?
C14 C15 C16 C11 0.0(3) . . . . ?
C14 C15 C16 C17 -177.93(19) . . . . ?
C11 C16 C17 C9 -38.46(19) . . . . ?
C15 C16 C17 C9 139.47(17) . . . . ?
C10 C9 C17 C16 55.64(15) . . . . ?
C18 C9 C17 C16 175.70(12) . . . . ?
C1 C9 C17 C16 -63.61(16) . . . . ?
C17 C9 C18 C19 -1.43(17) . . . . ?
C10 C9 C18 C19 117.93(13) . . . . ?
C1 C9 C18 C19 -127.55(12) . . . . ?
C17 C9 C18 C25 125.80(13) . . . . ?
C10 C9 C18 C25 -114.84(13) . . . . ?
C1 C9 C18 C25 -0.32(13) . . . . ?
C25 C18 C19 C20 125.64(16) . . . . ?
C9 C18 C19 C20 -111.63(15) . . . . ?
C25 C18 C19 C24 -51.34(19) . . . . ?
C9 C18 C19 C24 71.39(18) . . . . ?
C24 C19 C20 C21 -0.2(3) . . . . ?
C18 C19 C20 C21 -177.37(16) . . . . ?
C19 C20 C21 C22 -0.6(3) . . . . ?
C20 C21 C22 C23 0.9(3) . . . . ?
C21 C22 C23 C24 -0.2(3) . . . . ?
C22 C23 C24 C19 -0.7(3) . . . . ?
C20 C19 C24 C23 0.9(2) . . . . ?
C18 C19 C24 C23 177.93(15) . . . . ?
C19 C18 C25 N1 154.07(12) . . . . ?
C9 C18 C25 N1 24.21(15) . . . . ?
C18 C25 N1 C26 -169.91(15) . . . . ?
C18 C25 N1 C1 -41.67(15) . . . . ?
C8 C1 N1 C25 168.45(11) . . . . ?
C2 C1 N1 C25 -78.71(14) . . . . ?
C9 C1 N1 C25 40.46(13) . . . . ?
C8 C1 N1 C26 -64.05(15) . . . . ?
C2 C1 N1 C26 48.79(17) . . . . ?
C9 C1 N1 C26 167.96(12) . . . . ?
O1 C2 N2 C3 -176.54(17) . . . . ?
C1 C2 N2 C3 1.40(19) . . . . ?
C4 C3 N2 C2 179.75(18) . . . . ?
C8 C3 N2 C2 0.4(2) . . . . ?
O2 C10 O3 C11 176.59(16) . . . . ?
C9 C10 O3 C11 -2.9(2) . . . . ?
C16 C11 O3 C10 26.0(2) . . . . ?
C12 C11 O3 C10 -154.60(15) . . . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
N2 H2 O1 0.90(2) 1.94(2) 2.8362(16) 169(2) 2_565

_diffrn_measured_fraction_theta_max 0.992
_diffrn_reflns_theta_full        25.00
_diffrn_measured_fraction_theta_full 0.999
_refine_diff_density_max         0.453
_refine_diff_density_min         -0.402
_refine_diff_density_rms         0.062
####################################################################### 
# 
# 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_final
_audit_block_doi                 10.5517/ccwz948
_database_code_depnum_ccdc_archive 'CCDC 833470'
loop_
_citation_id
_citation_doi
_citation_year
1 10.1055/s-0031-1289704 2012
_audit_update_record             
;
2011-07-08 deposited with the CCDC.
2014-12-22 downloaded from the CCDC.
;
#TrackingRef 'DR.M.B. Cry.cif.txt'


_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           ?
_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                   11.0752(3)
_cell_length_b                   10.8473(2)
_cell_length_c                   18.1152(4)
_cell_angle_alpha                90.00
_cell_angle_beta                 103.625(2)
_cell_angle_gamma                90.00
_cell_volume                     2115.04(8)
_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    1.371
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             920
_exptl_absorpt_coefficient_mu    0.090
_exptl_absorpt_correction_type   none
_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            20021
_diffrn_reflns_av_R_equivalents  0.0380
_diffrn_reflns_av_sigmaI/netI    0.0446
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_l_min       -24
_diffrn_reflns_limit_l_max       24
_diffrn_reflns_theta_min         1.89
_diffrn_reflns_theta_max         28.36
_reflns_number_total             5270
_reflns_number_gt                3272
_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)+(0.0513P)²+0.2681P] 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         5270
_refine_ls_number_parameters     298
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0868
_refine_ls_R_factor_gt           0.0447
_refine_ls_wR_factor_ref         0.1184
_refine_ls_wR_factor_gt          0.0997
_refine_ls_goodness_of_fit_ref   1.014
_refine_ls_restrained_S_all      1.014
_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 0.94204(14) 0.32582(14) 0.12636(9) 0.0370(4) Uani 1 1 d . . .
C2 C 0.99338(16) 0.35009(17) 0.20177(10) 0.0500(4) Uani 1 1 d . . .
H2 H 1.0504 0.4136 0.2162 0.060 Uiso 1 1 calc R . .
C3 C 0.95762(17) 0.27721(18) 0.25555(10) 0.0525(5) Uani 1 1 d . . .
H3 H 0.9915 0.2913 0.3069 0.063 Uiso 1 1 calc R . .
C4 C 0.87236(17) 0.18401(16) 0.23382(9) 0.0479(4) Uani 1 1 d . . .
H4 H 0.8494 0.1356 0.2706 0.057 Uiso 1 1 calc R . .
C5 C 0.82045(15) 0.16152(15) 0.15776(9) 0.0410(4) Uani 1 1 d . . .
H5 H 0.7624 0.0988 0.1436 0.049 Uiso 1 1 calc R . .
C6 C 0.85517(14) 0.23257(13) 0.10274(8) 0.0330(3) Uani 1 1 d . . .
C7 C 0.81455(14) 0.23446(12) 0.01629(8) 0.0312(3) Uani 1 1 d . . .
C8 C 0.89388(14) 0.34383(13) -0.00240(9) 0.0353(4) Uani 1 1 d . . .
C9 C 0.66811(13) 0.25211(12) -0.02233(8) 0.0301(3) Uani 1 1 d . . .
C10 C 0.64335(14) 0.15097(13) -0.08479(8) 0.0319(3) Uani 1 1 d . . .
H10 H 0.6189 0.0769 -0.0609 0.038 Uiso 1 1 calc R . .
C11 C 0.77264(14) 0.12397(13) -0.09797(9) 0.0345(4) Uani 1 1 d . . .
H11 H 0.7969 0.1866 -0.1307 0.041 Uiso 1 1 calc R . .
C12 C 0.78852(17) -0.00565(14) -0.12690(10) 0.0458(4) Uani 1 1 d . . .
H12A H 0.7129 -0.0332 -0.1618 0.055 Uiso 1 1 calc R . .
H12B H 0.8562 -0.0084 -0.1525 0.055 Uiso 1 1 calc R . .
C13 C 0.81755(18) -0.08489(15) -0.05536(10) 0.0531(5) Uani 1 1 d . . .
H13A H 0.8907 -0.1350 -0.0537 0.064 Uiso 1 1 calc R . .
H13B H 0.7483 -0.1390 -0.0543 0.064 Uiso 1 1 calc R . .
C14 C 0.84037(16) 0.00367(13) 0.01193(9) 0.0430(4) Uani 1 1 d . . .
H14A H 0.7706 0.0035 0.0358 0.052 Uiso 1 1 calc R . .
H14B H 0.9149 -0.0189 0.0495 0.052 Uiso 1 1 calc R . .
C15 C 0.54307(14) 0.17205(13) -0.15594(8) 0.0347(4) Uani 1 1 d . . .
C16 C 0.43686(17) 0.10201(15) -0.16771(11) 0.0545(5) Uani 1 1 d . . .
H16 H 0.4259 0.0474 -0.1303 0.065 Uiso 1 1 calc R . .
C17 C 0.3458(2) 0.11169(18) -0.23462(13) 0.0751(7) Uani 1 1 d . . .
H17 H 0.2751 0.0627 -0.2418 0.090 Uiso 1 1 calc R . .
C18 C 0.3586(2) 0.19170(18) -0.28982(11) 0.0660(6) Uani 1 1 d . . .
H18 H 0.2968 0.1980 -0.3344 0.079 Uiso 1 1 calc R . .
C19 C 0.4628(2) 0.26278(18) -0.27950(10) 0.0560(5) Uani 1 1 d . . .
H19 H 0.4720 0.3183 -0.3169 0.067 Uiso 1 1 calc R . .
C20 C 0.55494(17) 0.25240(16) -0.21343(9) 0.0459(4) Uani 1 1 d . . .
H20 H 0.6263 0.3002 -0.2074 0.055 Uiso 1 1 calc R . .
C21 C 0.63305(15) 0.38439(13) -0.05079(8) 0.0361(4) Uani 1 1 d . . .
H21A H 0.6783 0.4073 -0.0885 0.043 Uiso 1 1 calc R . .
H21B H 0.5448 0.3890 -0.0741 0.043 Uiso 1 1 calc R . .
C22 C 0.59011(14) 0.22630(14) 0.03510(8) 0.0360(4) Uani 1 1 d . . .
C23 C 0.66522(15) 0.47058(13) 0.01575(9) 0.0381(4) Uani 1 1 d . . .
C24 C 0.64345(15) 0.42905(14) 0.08361(9) 0.0393(4) Uani 1 1 d . . .
C25 C 0.67621(17) 0.49490(17) 0.15018(10) 0.0516(5) Uani 1 1 d . . .
H25 H 0.6609 0.4639 0.1950 0.062 Uiso 1 1 calc R . .
C26 C 0.7320(2) 0.60759(18) 0.14891(12) 0.0643(6) Uani 1 1 d . . .
H26 H 0.7558 0.6534 0.1934 0.077 Uiso 1 1 calc R . .
C27 C 0.7530(2) 0.65307(17) 0.08191(12) 0.0678(6) Uani 1 1 d . . .
H27 H 0.7894 0.7302 0.0812 0.081 Uiso 1 1 calc R . .
C28 C 0.72006(18) 0.58473(15) 0.01603(10) 0.0531(5) Uani 1 1 d . . .
H28 H 0.7351 0.6160 -0.0288 0.064 Uiso 1 1 calc R . .
N1 N 0.96422(12) 0.38759(12) 0.06335(7) 0.0418(3) Uani 1 1 d . . .
H1 H 1.0167 0.4468 0.0661 0.050 Uiso 1 1 calc R . .
N2 N 0.85492(11) 0.12657(10) -0.02131(7) 0.0349(3) Uani 1 1 d . . .
O1 O 0.89551(11) 0.38302(10) -0.06553(6) 0.0458(3) Uani 1 1 d . . .
O2 O 0.53422(12) 0.13338(11) 0.03960(7) 0.0527(3) Uani 1 1 d . . .
O3 O 0.58260(10) 0.31720(10) 0.08553(6) 0.0435(3) Uani 1 1 d . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C1 C2 1.376(2) . ?
C1 C6 1.392(2) . ?
C1 N1 1.394(2) . ?
C2 C3 1.383(2) . ?
C2 H2 0.9300 . ?
C3 C4 1.376(3) . ?
C3 H3 0.9300 . ?
C4 C5 1.384(2) . ?
C4 H4 0.9300 . ?
C5 C6 1.384(2) . ?
C5 H5 0.9300 . ?
C6 C7 1.524(2) . ?
C7 N2 1.4755(18) . ?
C7 C8 1.560(2) . ?
C7 C9 1.619(2) . ?
C8 O1 1.2241(18) . ?
C8 N1 1.347(2) . ?
C9 C22 1.527(2) . ?
C9 C21 1.5431(19) . ?
C9 C10 1.5535(19) . ?
C10 C15 1.507(2) . ?
C10 C11 1.534(2) . ?
C10 H10 0.9800 . ?
C11 N2 1.4708(19) . ?
C11 C12 1.525(2) . ?
C11 H11 0.9800 . ?
C12 C13 1.525(2) . ?
C12 H12A 0.9700 . ?
C12 H12B 0.9700 . ?
C13 C14 1.526(2) . ?
C13 H13A 0.9700 . ?
C13 H13B 0.9700 . ?
C14 N2 1.4872(19) . ?
C14 H14A 0.9700 . ?
C14 H14B 0.9700 . ?
C15 C16 1.374(2) . ?
C15 C20 1.388(2) . ?
C16 C17 1.386(3) . ?
C16 H16 0.9300 . ?
C17 C18 1.357(3) . ?
C17 H17 0.9300 . ?
C18 C19 1.364(3) . ?
C18 H18 0.9300 . ?
C19 C20 1.382(2) . ?
C19 H19 0.9300 . ?
C20 H20 0.9300 . ?
C21 C23 1.500(2) . ?
C21 H21A 0.9700 . ?
C21 H21B 0.9700 . ?
C22 O2 1.1957(18) . ?
C22 O3 1.3599(18) . ?
C23 C28 1.379(2) . ?
C23 C24 1.383(2) . ?
C24 C25 1.375(2) . ?
C24 O3 1.3922(19) . ?
C25 C26 1.372(3) . ?
C25 H25 0.9300 . ?
C26 C27 1.379(3) . ?
C26 H26 0.9300 . ?
C27 C28 1.379(3) . ?
C27 H27 0.9300 . ?
C28 H28 0.9300 . ?
N1 H1 0.8600 . ?

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 C1 C6 122.57(15) . . ?
C2 C1 N1 127.56(15) . . ?
C6 C1 N1 109.86(13) . . ?
C1 C2 C3 118.04(16) . . ?
C1 C2 H2 121.0 . . ?
C3 C2 H2 121.0 . . ?
C4 C3 C2 120.64(16) . . ?
C4 C3 H3 119.7 . . ?
C2 C3 H3 119.7 . . ?
C3 C4 C5 120.69(16) . . ?
C3 C4 H4 119.7 . . ?
C5 C4 H4 119.7 . . ?
C4 C5 C6 119.88(15) . . ?
C4 C5 H5 120.1 . . ?
C6 C5 H5 120.1 . . ?
C5 C6 C1 118.18(14) . . ?
C5 C6 C7 133.04(14) . . ?
C1 C6 C7 108.75(12) . . ?
N2 C7 C6 114.55(11) . . ?
N2 C7 C8 104.80(11) . . ?
C6 C7 C8 100.85(11) . . ?
N2 C7 C9 106.02(11) . . ?
C6 C7 C9 117.95(12) . . ?
C8 C7 C9 111.98(11) . . ?
O1 C8 N1 124.82(14) . . ?
O1 C8 C7 126.85(14) . . ?
N1 C8 C7 108.30(13) . . ?
C22 C9 C21 105.07(12) . . ?
C22 C9 C10 109.62(12) . . ?
C21 C9 C10 115.21(12) . . ?
C22 C9 C7 110.73(11) . . ?
C21 C9 C7 113.70(11) . . ?
C10 C9 C7 102.60(11) . . ?
C15 C10 C11 114.99(12) . . ?
C15 C10 C9 118.93(12) . . ?
C11 C10 C9 103.71(11) . . ?
C15 C10 H10 106.1 . . ?
C11 C10 H10 106.1 . . ?
C9 C10 H10 106.1 . . ?
N2 C11 C12 104.25(12) . . ?
N2 C11 C10 104.06(12) . . ?
C12 C11 C10 114.63(13) . . ?
N2 C11 H11 111.2 . . ?
C12 C11 H11 111.2 . . ?
C10 C11 H11 111.2 . . ?
C13 C12 C11 104.24(13) . . ?
C13 C12 H12A 110.9 . . ?
C11 C12 H12A 110.9 . . ?
C13 C12 H12B 110.9 . . ?
C11 C12 H12B 110.9 . . ?
H12A C12 H12B 108.9 . . ?
C12 C13 C14 106.63(13) . . ?
C12 C13 H13A 110.4 . . ?
C14 C13 H13A 110.4 . . ?
C12 C13 H13B 110.4 . . ?
C14 C13 H13B 110.4 . . ?
H13A C13 H13B 108.6 . . ?
N2 C14 C13 104.73(13) . . ?
N2 C14 H14A 110.8 . . ?
C13 C14 H14A 110.8 . . ?
N2 C14 H14B 110.8 . . ?
C13 C14 H14B 110.8 . . ?
H14A C14 H14B 108.9 . . ?
C16 C15 C20 117.37(15) . . ?
C16 C15 C10 118.69(14) . . ?
C20 C15 C10 123.77(14) . . ?
C15 C16 C17 120.91(18) . . ?
C15 C16 H16 119.5 . . ?
C17 C16 H16 119.5 . . ?
C18 C17 C16 120.82(19) . . ?
C18 C17 H17 119.6 . . ?
C16 C17 H17 119.6 . . ?
C17 C18 C19 119.51(18) . . ?
C17 C18 H18 120.2 . . ?
C19 C18 H18 120.2 . . ?
C18 C19 C20 120.06(17) . . ?
C18 C19 H19 120.0 . . ?
C20 C19 H19 120.0 . . ?
C19 C20 C15 121.33(17) . . ?
C19 C20 H20 119.3 . . ?
C15 C20 H20 119.3 . . ?
C23 C21 C9 108.51(12) . . ?
C23 C21 H21A 110.0 . . ?
C9 C21 H21A 110.0 . . ?
C23 C21 H21B 110.0 . . ?
C9 C21 H21B 110.0 . . ?
H21A C21 H21B 108.4 . . ?
O2 C22 O3 116.80(14) . . ?
O2 C22 C9 125.89(14) . . ?
O3 C22 C9 117.31(13) . . ?
C28 C23 C24 117.27(15) . . ?
C28 C23 C21 125.71(15) . . ?
C24 C23 C21 116.94(14) . . ?
C25 C24 C23 123.05(16) . . ?
C25 C24 O3 117.40(15) . . ?
C23 C24 O3 119.53(14) . . ?
C26 C25 C24 118.35(18) . . ?
C26 C25 H25 120.8 . . ?
C24 C25 H25 120.8 . . ?
C25 C26 C27 120.20(18) . . ?
C25 C26 H26 119.9 . . ?
C27 C26 H26 119.9 . . ?
C28 C27 C26 120.29(18) . . ?
C28 C27 H27 119.9 . . ?
C26 C27 H27 119.9 . . ?
C23 C28 C27 120.83(17) . . ?
C23 C28 H28 119.6 . . ?
C27 C28 H28 119.6 . . ?
C8 N1 C1 112.20(13) . . ?
C8 N1 H1 123.9 . . ?
C1 N1 H1 123.9 . . ?
C11 N2 C7 105.27(11) . . ?
C11 N2 C14 105.25(11) . . ?
C7 N2 C14 116.78(12) . . ?
C22 O3 C24 120.57(12) . . ?

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 0.9(3) . . . . ?
N1 C1 C2 C3 179.66(16) . . . . ?
C1 C2 C3 C4 -0.5(3) . . . . ?
C2 C3 C4 C5 -0.2(3) . . . . ?
C3 C4 C5 C6 0.6(3) . . . . ?
C4 C5 C6 C1 -0.3(2) . . . . ?
C4 C5 C6 C7 -178.11(16) . . . . ?
C2 C1 C6 C5 -0.5(2) . . . . ?
N1 C1 C6 C5 -179.45(14) . . . . ?
C2 C1 C6 C7 177.87(15) . . . . ?
N1 C1 C6 C7 -1.11(17) . . . . ?
C5 C6 C7 N2 -70.0(2) . . . . ?
C1 C6 C7 N2 111.95(14) . . . . ?
C5 C6 C7 C8 178.02(17) . . . . ?
C1 C6 C7 C8 0.02(15) . . . . ?
C5 C6 C7 C9 55.8(2) . . . . ?
C1 C6 C7 C9 -122.19(13) . . . . ?
N2 C7 C8 O1 60.42(19) . . . . ?
C6 C7 C8 O1 179.64(15) . . . . ?
C9 C7 C8 O1 -54.06(19) . . . . ?
N2 C7 C8 N1 -118.12(13) . . . . ?
C6 C7 C8 N1 1.10(15) . . . . ?
C9 C7 C8 N1 127.40(13) . . . . ?
N2 C7 C9 C22 113.13(12) . . . . ?
C6 C7 C9 C22 -16.78(16) . . . . ?
C8 C7 C9 C22 -133.13(12) . . . . ?
N2 C7 C9 C21 -128.85(12) . . . . ?
C6 C7 C9 C21 101.23(14) . . . . ?
C8 C7 C9 C21 -15.12(16) . . . . ?
N2 C7 C9 C10 -3.76(13) . . . . ?
C6 C7 C9 C10 -133.68(12) . . . . ?
C8 C7 C9 C10 109.97(12) . . . . ?
C22 C9 C10 C15 91.87(15) . . . . ?
C21 C9 C10 C15 -26.35(19) . . . . ?
C7 C9 C10 C15 -150.44(12) . . . . ?
C22 C9 C10 C11 -138.95(12) . . . . ?
C21 C9 C10 C11 102.83(14) . . . . ?
C7 C9 C10 C11 -21.26(13) . . . . ?
C15 C10 C11 N2 171.47(11) . . . . ?
C9 C10 C11 N2 39.93(13) . . . . ?
C15 C10 C11 C12 -75.33(16) . . . . ?
C9 C10 C11 C12 153.13(12) . . . . ?
N2 C11 C12 C13 30.22(17) . . . . ?
C10 C11 C12 C13 -82.86(16) . . . . ?
C11 C12 C13 C14 -9.99(19) . . . . ?
C12 C13 C14 N2 -13.54(18) . . . . ?
C11 C10 C15 C16 125.68(16) . . . . ?
C9 C10 C15 C16 -110.51(17) . . . . ?
C11 C10 C15 C20 -49.57(19) . . . . ?
C9 C10 C15 C20 74.24(19) . . . . ?
C20 C15 C16 C17 0.1(3) . . . . ?
C10 C15 C16 C17 -175.41(17) . . . . ?
C15 C16 C17 C18 -0.8(3) . . . . ?
C16 C17 C18 C19 0.5(3) . . . . ?
C17 C18 C19 C20 0.5(3) . . . . ?
C18 C19 C20 C15 -1.2(3) . . . . ?
C16 C15 C20 C19 0.8(2) . . . . ?
C10 C15 C20 C19 176.14(15) . . . . ?
C22 C9 C21 C23 60.55(15) . . . . ?
C10 C9 C21 C23 -178.72(12) . . . . ?
C7 C9 C21 C23 -60.68(16) . . . . ?
C21 C9 C22 O2 135.79(16) . . . . ?
C10 C9 C22 O2 11.4(2) . . . . ?
C7 C9 C22 O2 -101.05(17) . . . . ?
C21 C9 C22 O3 -43.79(16) . . . . ?
C10 C9 C22 O3 -168.14(12) . . . . ?
C7 C9 C22 O3 79.37(15) . . . . ?
C9 C21 C23 C28 138.04(16) . . . . ?
C9 C21 C23 C24 -38.57(19) . . . . ?
C28 C23 C24 C25 -1.4(2) . . . . ?
C21 C23 C24 C25 175.51(15) . . . . ?
C28 C23 C24 O3 176.77(14) . . . . ?
C21 C23 C24 O3 -6.3(2) . . . . ?
C23 C24 C25 C26 0.6(3) . . . . ?
O3 C24 C25 C26 -177.56(16) . . . . ?
C24 C25 C26 C27 0.7(3) . . . . ?
C25 C26 C27 C28 -1.2(3) . . . . ?
C24 C23 C28 C27 0.9(3) . . . . ?
C21 C23 C28 C27 -175.75(18) . . . . ?
C26 C27 C28 C23 0.4(3) . . . . ?
O1 C8 N1 C1 179.53(15) . . . . ?
C7 C8 N1 C1 -1.89(17) . . . . ?
C2 C1 N1 C8 -176.97(16) . . . . ?
C6 C1 N1 C8 1.95(19) . . . . ?
C12 C11 N2 C7 -163.62(12) . . . . ?
C10 C11 N2 C7 -43.16(13) . . . . ?
C12 C11 N2 C14 -39.67(15) . . . . ?
C10 C11 N2 C14 80.78(13) . . . . ?
C6 C7 N2 C11 160.58(12) . . . . ?
C8 C7 N2 C11 -89.86(13) . . . . ?
C9 C7 N2 C11 28.73(13) . . . . ?
C6 C7 N2 C14 44.28(17) . . . . ?
C8 C7 N2 C14 153.84(12) . . . . ?
C9 C7 N2 C14 -87.57(14) . . . . ?
C13 C14 N2 C11 33.01(16) . . . . ?
C13 C14 N2 C7 149.32(13) . . . . ?
O2 C22 O3 C24 -179.13(14) . . . . ?
C9 C22 O3 C24 0.5(2) . . . . ?
C25 C24 O3 C22 -153.93(15) . . . . ?
C23 C24 O3 C22 27.8(2) . . . . ?

_diffrn_measured_fraction_theta_max 0.995
_diffrn_reflns_theta_full        28.36
_diffrn_measured_fraction_theta_full 0.995
_refine_diff_density_max         0.233
_refine_diff_density_min         -0.224
_refine_diff_density_rms         0.039


####################################################################### 
# 
# 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
_database_code_depnum_ccdc_archive 'CCDC 976506'
_audit_update_record             
;
2013-12-11 deposited with the CCDC.
2014-12-22 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C32 H36 N2 O4 S'
_chemical_formula_weight         544.69

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                   10.3767(4)
_cell_length_b                   10.8064(4)
_cell_length_c                   15.0426(5)
_cell_angle_alpha                75.845(2)
_cell_angle_beta                 76.824(2)
_cell_angle_gamma                62.065(2)
_cell_volume                     1432.29(9)
_cell_formula_units_Z            2
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    7173
_cell_measurement_theta_min      2.12
_cell_measurement_theta_max      31.44

_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.35
_exptl_crystal_size_mid          0.35
_exptl_crystal_size_min          0.30
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.263
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             580
_exptl_absorpt_coefficient_mu    0.152
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.9086
_exptl_absorpt_correction_T_max  0.9557
_exptl_absorpt_process_details   'SADABS (Bruker, 2004)'

_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            28853
_diffrn_reflns_av_R_equivalents  0.0245
_diffrn_reflns_av_sigmaI/netI    0.0191
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_theta_min         2.16
_diffrn_reflns_theta_max         27.50
_reflns_number_total             6574
_reflns_number_gt                5487
_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    'SIR92 (Altomare et al., 1993)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_molecular_graphics    
'ORTEP3 (Farrugia, 1997) and Mercury (Macrae et al., 2008)'
_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)+(0.0661P)²+0.5189P] 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         6574
_refine_ls_number_parameters     356
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0545
_refine_ls_R_factor_gt           0.0448
_refine_ls_wR_factor_ref         0.1289
_refine_ls_wR_factor_gt          0.1190
_refine_ls_goodness_of_fit_ref   1.030
_refine_ls_restrained_S_all      1.030
_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 1.05080(17) 0.16279(16) 0.30942(10) 0.0341(3) Uani 1 1 d . . .
C2 C 0.9820(2) 0.1624(2) 0.40054(11) 0.0464(4) Uani 1 1 d . . .
H2 H 0.8837 0.1788 0.4133 0.056 Uiso 1 1 calc R . .
C3 C 1.0585(2) 0.1377(2) 0.47185(12) 0.0541(5) Uani 1 1 d . . .
H3 H 1.0114 0.1376 0.5324 0.065 Uiso 1 1 calc R . .
C4 C 1.2032(2) 0.1133(2) 0.45433(12) 0.0552(5) Uani 1 1 d . . .
H4 H 1.2546 0.0961 0.5026 0.066 Uiso 1 1 calc R . .
C5 C 1.2715(2) 0.1147(2) 0.36456(12) 0.0461(4) Uani 1 1 d . . .
H5 H 1.3699 0.0978 0.3528 0.055 Uiso 1 1 calc R . .
C6 C 1.19711(17) 0.14079(16) 0.29079(10) 0.0340(3) Uani 1 1 d . . .
C7 C 1.27721(15) 0.14620(15) 0.19401(10) 0.0302(3) Uani 1 1 d . . .
H7 H 1.3772 0.0691 0.1929 0.036 Uiso 1 1 calc R . .
C8 C 1.4079(2) 0.2944(2) 0.18320(13) 0.0493(4) Uani 1 1 d . . .
H8A H 1.4904 0.2018 0.1939 0.059 Uiso 1 1 calc R . .
H8B H 1.3785 0.3385 0.2380 0.059 Uiso 1 1 calc R . .
C9 C 1.4475(2) 0.3864(2) 0.09938(15) 0.0560(5) Uani 1 1 d . . .
H9A H 1.5484 0.3713 0.0952 0.067 Uiso 1 1 calc R . .
H9B H 1.3822 0.4861 0.1004 0.067 Uiso 1 1 calc R . .
C10 C 1.4273(2) 0.3354(2) 0.02074(14) 0.0558(5) Uani 1 1 d . . .
H10A H 1.5106 0.2470 0.0074 0.067 Uiso 1 1 calc R . .
H10B H 1.4139 0.4057 -0.0349 0.067 Uiso 1 1 calc R . .
C11 C 1.28837(17) 0.31456(16) 0.05833(10) 0.0350(3) Uani 1 1 d . . .
H11 H 1.2023 0.4033 0.0419 0.042 Uiso 1 1 calc R . .
C12 C 1.27846(15) 0.19219(14) 0.03101(9) 0.0291(3) Uani 1 1 d . . .
H12 H 1.3795 0.1178 0.0228 0.035 Uiso 1 1 calc R . .
C13 C 1.20020(14) 0.13708(14) 0.12206(9) 0.0272(3) Uani 1 1 d . . .
C14 C 1.03636(14) 0.23385(14) 0.14096(9) 0.0284(3) Uani 1 1 d . . .
H14A H 1.0214 0.3303 0.1379 0.034 Uiso 1 1 calc R . .
H14B H 0.9851 0.2336 0.0946 0.034 Uiso 1 1 calc R . .
C15 C 0.68460(16) 0.33133(17) 0.28796(10) 0.0364(3) Uani 1 1 d . . .
C16 C 0.6707(2) 0.4609(2) 0.23710(13) 0.0503(4) Uani 1 1 d . . .
H16 H 0.7345 0.4648 0.1830 0.060 Uiso 1 1 calc R . .
C17 C 0.5624(2) 0.5847(2) 0.26641(15) 0.0589(5) Uani 1 1 d . . .
H17 H 0.5545 0.6717 0.2323 0.071 Uiso 1 1 calc R . .
C18 C 0.4653(2) 0.5812(2) 0.34582(15) 0.0586(5) Uani 1 1 d . . .
C19 C 0.4795(2) 0.4512(3) 0.39490(14) 0.0650(6) Uani 1 1 d . . .
H19 H 0.4145 0.4475 0.4483 0.078 Uiso 1 1 calc R . .
C20 C 0.5880(2) 0.3256(2) 0.36688(13) 0.0524(4) Uani 1 1 d . . .
H20 H 0.5956 0.2386 0.4009 0.063 Uiso 1 1 calc R . .
C21 C 0.3480(3) 0.7174(3) 0.3779(2) 0.0947(9) Uani 1 1 d . . .
H21A H 0.2947 0.6956 0.4358 0.142 Uiso 1 1 calc R . .
H21B H 0.2815 0.7701 0.3326 0.142 Uiso 1 1 calc R . .
H21C H 0.3934 0.7731 0.3857 0.142 Uiso 1 1 calc R . .
C22 C 1.22872(17) -0.01392(15) 0.12108(10) 0.0337(3) Uani 1 1 d . . .
C23 C 1.1406(3) -0.1526(2) 0.07637(17) 0.0626(5) Uani 1 1 d . . .
H23A H 1.2043 -0.1833 0.0209 0.094 Uiso 1 1 calc R . .
H23B H 1.0451 -0.1443 0.0741 0.094 Uiso 1 1 calc R . .
H23C H 1.1809 -0.2207 0.1290 0.094 Uiso 1 1 calc R . .
C24 C 1.21829(15) 0.22452(14) -0.05832(9) 0.0288(3) Uani 1 1 d . . .
C25 C 1.09707(18) 0.34868(16) -0.08414(11) 0.0380(3) Uani 1 1 d . . .
H25 H 1.0457 0.4129 -0.0429 0.046 Uiso 1 1 calc R . .
C26 C 1.05001(19) 0.38010(17) -0.16931(11) 0.0420(4) Uani 1 1 d . . .
H26 H 0.9687 0.4649 -0.1844 0.050 Uiso 1 1 calc R . .
C27 C 1.12259(19) 0.28669(17) -0.23236(11) 0.0404(3) Uani 1 1 d . . .
C28 C 1.2399(2) 0.15966(19) -0.20548(12) 0.0477(4) Uani 1 1 d . . .
H28 H 1.2879 0.0932 -0.2454 0.057 Uiso 1 1 calc R . .
C29 C 1.28719(18) 0.12947(17) -0.12070(11) 0.0417(4) Uani 1 1 d . . .
H29 H 1.3670 0.0435 -0.1051 0.050 Uiso 1 1 calc R . .
C30 C 1.0801(3) 0.3210(2) -0.32853(12) 0.0582(5) Uani 1 1 d . . .
H30 H 1.1015 0.2310 -0.3460 0.070 Uiso 1 1 calc R . .
C31 C 1.1756(5) 0.3808(6) -0.39666(19) 0.1412(18) Uani 1 1 d . . .
H31A H 1.1602 0.3868 -0.4584 0.212 Uiso 1 1 calc R . .
H31B H 1.2771 0.3200 -0.3894 0.212 Uiso 1 1 calc R . .
H31C H 1.1505 0.4738 -0.3856 0.212 Uiso 1 1 calc R . .
C32 C 0.9206(4) 0.4160(5) -0.3346(2) 0.1284(15) Uani 1 1 d . . .
H32A H 0.8623 0.3749 -0.2910 0.193 Uiso 1 1 calc R . .
H32B H 0.9005 0.4270 -0.3960 0.193 Uiso 1 1 calc R . .
H32C H 0.8966 0.5071 -0.3208 0.193 Uiso 1 1 calc R . .
N1 N 0.97766(13) 0.18269(14) 0.23349(8) 0.0344(3) Uani 1 1 d . . .
N2 N 1.28432(14) 0.28224(13) 0.16012(9) 0.0341(3) Uani 1 1 d . . .
O1 O 0.82474(14) 0.05705(13) 0.31783(9) 0.0500(3) Uani 1 1 d . . .
O2 O 0.79381(13) 0.17923(14) 0.15760(8) 0.0471(3) Uani 1 1 d . . .
O3 O 1.3328(2) -0.11586(14) 0.14597(14) 0.0855(6) Uani 1 1 d . . .
O4 O 1.12766(14) -0.01694(12) 0.08404(10) 0.0499(3) Uani 1 1 d . . .
S1 S 0.82019(4) 0.17412(4) 0.24754(3) 0.03562(11) 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 C6 1.393(2) . ?
C1 C2 1.394(2) . ?
C1 N1 1.4314(18) . ?
C2 C3 1.379(2) . ?
C2 H2 0.9300 . ?
C3 C4 1.370(3) . ?
C3 H3 0.9300 . ?
C4 C5 1.375(3) . ?
C4 H4 0.9300 . ?
C5 C6 1.393(2) . ?
C5 H5 0.9300 . ?
C6 C7 1.505(2) . ?
C7 N2 1.4644(18) . ?
C7 C13 1.5296(18) . ?
C7 H7 0.9800 . ?
C8 N2 1.4716(19) . ?
C8 C9 1.510(3) . ?
C8 H8A 0.9700 . ?
C8 H8B 0.9700 . ?
C9 C10 1.513(3) . ?
C9 H9A 0.9700 . ?
C9 H9B 0.9700 . ?
C10 C11 1.522(2) . ?
C10 H10A 0.9700 . ?
C10 H10B 0.9700 . ?
C11 N2 1.4802(19) . ?
C11 C12 1.530(2) . ?
C11 H11 0.9800 . ?
C12 C24 1.5053(18) . ?
C12 C13 1.5611(19) . ?
C12 H12 0.9800 . ?
C13 C22 1.5192(19) . ?
C13 C14 1.5245(18) . ?
C14 N1 1.4720(18) . ?
C14 H14A 0.9700 . ?
C14 H14B 0.9700 . ?
C15 C20 1.377(2) . ?
C15 C16 1.380(2) . ?
C15 S1 1.7638(16) . ?
C16 C17 1.379(3) . ?
C16 H16 0.9300 . ?
C17 C18 1.381(3) . ?
C17 H17 0.9300 . ?
C18 C19 1.374(3) . ?
C18 C21 1.511(3) . ?
C19 C20 1.386(3) . ?
C19 H19 0.9300 . ?
C20 H20 0.9300 . ?
C21 H21A 0.9600 . ?
C21 H21B 0.9600 . ?
C21 H21C 0.9600 . ?
C22 O3 1.1784(19) . ?
C22 O4 1.3109(19) . ?
C23 O4 1.440(2) . ?
C23 H23A 0.9600 . ?
C23 H23B 0.9600 . ?
C23 H23C 0.9600 . ?
C24 C25 1.386(2) . ?
C24 C29 1.387(2) . ?
C25 C26 1.383(2) . ?
C25 H25 0.9300 . ?
C26 C27 1.384(2) . ?
C26 H26 0.9300 . ?
C27 C28 1.385(2) . ?
C27 C30 1.517(2) . ?
C28 C29 1.380(2) . ?
C28 H28 0.9300 . ?
C29 H29 0.9300 . ?
C30 C32 1.494(4) . ?
C30 C31 1.505(4) . ?
C30 H30 0.9800 . ?
C31 H31A 0.9600 . ?
C31 H31B 0.9600 . ?
C31 H31C 0.9600 . ?
C32 H32A 0.9600 . ?
C32 H32B 0.9600 . ?
C32 H32C 0.9600 . ?
N1 S1 1.6426(13) . ?
O1 S1 1.4259(13) . ?
O2 S1 1.4236(12) . ?

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
C6 C1 C2 119.32(14) . . ?
C6 C1 N1 118.16(13) . . ?
C2 C1 N1 122.52(14) . . ?
C3 C2 C1 120.47(17) . . ?
C3 C2 H2 119.8 . . ?
C1 C2 H2 119.8 . . ?
C4 C3 C2 120.60(16) . . ?
C4 C3 H3 119.7 . . ?
C2 C3 H3 119.7 . . ?
C3 C4 C5 119.28(16) . . ?
C3 C4 H4 120.4 . . ?
C5 C4 H4 120.4 . . ?
C4 C5 C6 121.63(17) . . ?
C4 C5 H5 119.2 . . ?
C6 C5 H5 119.2 . . ?
C1 C6 C5 118.68(14) . . ?
C1 C6 C7 122.56(12) . . ?
C5 C6 C7 118.74(14) . . ?
N2 C7 C6 111.62(12) . . ?
N2 C7 C13 103.11(11) . . ?
C6 C7 C13 113.69(12) . . ?
N2 C7 H7 109.4 . . ?
C6 C7 H7 109.4 . . ?
C13 C7 H7 109.4 . . ?
N2 C8 C9 104.33(13) . . ?
N2 C8 H8A 110.9 . . ?
C9 C8 H8A 110.9 . . ?
N2 C8 H8B 110.9 . . ?
C9 C8 H8B 110.9 . . ?
H8A C8 H8B 108.9 . . ?
C8 C9 C10 102.27(15) . . ?
C8 C9 H9A 111.3 . . ?
C10 C9 H9A 111.3 . . ?
C8 C9 H9B 111.3 . . ?
C10 C9 H9B 111.3 . . ?
H9A C9 H9B 109.2 . . ?
C9 C10 C11 102.61(15) . . ?
C9 C10 H10A 111.2 . . ?
C11 C10 H10A 111.2 . . ?
C9 C10 H10B 111.2 . . ?
C11 C10 H10B 111.2 . . ?
H10A C10 H10B 109.2 . . ?
N2 C11 C10 105.55(12) . . ?
N2 C11 C12 105.69(11) . . ?
C10 C11 C12 117.58(14) . . ?
N2 C11 H11 109.2 . . ?
C10 C11 H11 109.2 . . ?
C12 C11 H11 109.2 . . ?
C24 C12 C11 116.12(11) . . ?
C24 C12 C13 118.84(11) . . ?
C11 C12 C13 102.11(11) . . ?
C24 C12 H12 106.3 . . ?
C11 C12 H12 106.3 . . ?
C13 C12 H12 106.3 . . ?
C22 C13 C14 111.83(11) . . ?
C22 C13 C7 112.77(11) . . ?
C14 C13 C7 107.95(11) . . ?
C22 C13 C12 109.72(11) . . ?
C14 C13 C12 113.51(11) . . ?
C7 C13 C12 100.59(11) . . ?
N1 C14 C13 109.09(11) . . ?
N1 C14 H14A 109.9 . . ?
C13 C14 H14A 109.9 . . ?
N1 C14 H14B 109.9 . . ?
C13 C14 H14B 109.9 . . ?
H14A C14 H14B 108.3 . . ?
C20 C15 C16 119.99(16) . . ?
C20 C15 S1 120.53(14) . . ?
C16 C15 S1 119.39(12) . . ?
C17 C16 C15 120.03(17) . . ?
C17 C16 H16 120.0 . . ?
C15 C16 H16 120.0 . . ?
C16 C17 C18 120.85(19) . . ?
C16 C17 H17 119.6 . . ?
C18 C17 H17 119.6 . . ?
C19 C18 C17 118.32(18) . . ?
C19 C18 C21 121.2(2) . . ?
C17 C18 C21 120.4(2) . . ?
C18 C19 C20 121.74(19) . . ?
C18 C19 H19 119.1 . . ?
C20 C19 H19 119.1 . . ?
C15 C20 C19 119.05(18) . . ?
C15 C20 H20 120.5 . . ?
C19 C20 H20 120.5 . . ?
C18 C21 H21A 109.5 . . ?
C18 C21 H21B 109.5 . . ?
H21A C21 H21B 109.5 . . ?
C18 C21 H21C 109.5 . . ?
H21A C21 H21C 109.5 . . ?
H21B C21 H21C 109.5 . . ?
O3 C22 O4 123.86(15) . . ?
O3 C22 C13 124.32(15) . . ?
O4 C22 C13 111.71(12) . . ?
O4 C23 H23A 109.5 . . ?
O4 C23 H23B 109.5 . . ?
H23A C23 H23B 109.5 . . ?
O4 C23 H23C 109.5 . . ?
H23A C23 H23C 109.5 . . ?
H23B C23 H23C 109.5 . . ?
C25 C24 C29 116.68(13) . . ?
C25 C24 C12 123.27(12) . . ?
C29 C24 C12 120.03(13) . . ?
C26 C25 C24 122.11(14) . . ?
C26 C25 H25 118.9 . . ?
C24 C25 H25 118.9 . . ?
C25 C26 C27 120.74(15) . . ?
C25 C26 H26 119.6 . . ?
C27 C26 H26 119.6 . . ?
C26 C27 C28 117.46(14) . . ?
C26 C27 C30 122.36(16) . . ?
C28 C27 C30 120.16(15) . . ?
C29 C28 C27 121.48(15) . . ?
C29 C28 H28 119.3 . . ?
C27 C28 H28 119.3 . . ?
C28 C29 C24 121.44(14) . . ?
C28 C29 H29 119.3 . . ?
C24 C29 H29 119.3 . . ?
C32 C30 C31 111.2(3) . . ?
C32 C30 C27 114.13(19) . . ?
C31 C30 C27 109.95(19) . . ?
C32 C30 H30 107.1 . . ?
C31 C30 H30 107.1 . . ?
C27 C30 H30 107.1 . . ?
C30 C31 H31A 109.5 . . ?
C30 C31 H31B 109.5 . . ?
H31A C31 H31B 109.5 . . ?
C30 C31 H31C 109.5 . . ?
H31A C31 H31C 109.5 . . ?
H31B C31 H31C 109.5 . . ?
C30 C32 H32A 109.5 . . ?
C30 C32 H32B 109.5 . . ?
H32A C32 H32B 109.5 . . ?
C30 C32 H32C 109.5 . . ?
H32A C32 H32C 109.5 . . ?
H32B C32 H32C 109.5 . . ?
C1 N1 C14 117.29(11) . . ?
C1 N1 S1 122.78(10) . . ?
C14 N1 S1 119.27(9) . . ?
C7 N2 C8 116.56(12) . . ?
C7 N2 C11 109.21(11) . . ?
C8 N2 C11 108.28(12) . . ?
C22 O4 C23 118.52(14) . . ?
O2 S1 O1 119.43(8) . . ?
O2 S1 N1 106.14(6) . . ?
O1 S1 N1 108.65(7) . . ?
O2 S1 C15 107.52(7) . . ?
O1 S1 C15 108.13(8) . . ?
N1 S1 C15 106.25(7) . . ?

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 -1.3(3) . . . . ?
N1 C1 C2 C3 177.65(16) . . . . ?
C1 C2 C3 C4 0.1(3) . . . . ?
C2 C3 C4 C5 0.5(3) . . . . ?
C3 C4 C5 C6 0.2(3) . . . . ?
C2 C1 C6 C5 1.9(2) . . . . ?
N1 C1 C6 C5 -177.04(14) . . . . ?
C2 C1 C6 C7 -177.18(15) . . . . ?
N1 C1 C6 C7 3.9(2) . . . . ?
C4 C5 C6 C1 -1.4(3) . . . . ?
C4 C5 C6 C7 177.70(17) . . . . ?
C1 C6 C7 N2 100.31(16) . . . . ?
C5 C6 C7 N2 -78.78(17) . . . . ?
C1 C6 C7 C13 -15.8(2) . . . . ?
C5 C6 C7 C13 165.09(14) . . . . ?
N2 C8 C9 C10 -38.0(2) . . . . ?
C8 C9 C10 C11 40.1(2) . . . . ?
C9 C10 C11 N2 -27.74(19) . . . . ?
C9 C10 C11 C12 -145.26(15) . . . . ?
N2 C11 C12 C24 155.46(11) . . . . ?
C10 C11 C12 C24 -87.09(17) . . . . ?
N2 C11 C12 C13 24.57(13) . . . . ?
C10 C11 C12 C13 142.02(14) . . . . ?
N2 C7 C13 C22 158.86(11) . . . . ?
C6 C7 C13 C22 -80.12(15) . . . . ?
N2 C7 C13 C14 -77.08(13) . . . . ?
C6 C7 C13 C14 43.93(15) . . . . ?
N2 C7 C13 C12 42.07(12) . . . . ?
C6 C7 C13 C12 163.08(11) . . . . ?
C24 C12 C13 C22 71.15(15) . . . . ?
C11 C12 C13 C22 -159.65(11) . . . . ?
C24 C12 C13 C14 -54.78(16) . . . . ?
C11 C12 C13 C14 74.43(13) . . . . ?
C24 C12 C13 C7 -169.82(11) . . . . ?
C11 C12 C13 C7 -40.61(12) . . . . ?
C22 C13 C14 N1 62.54(14) . . . . ?
C7 C13 C14 N1 -62.08(14) . . . . ?
C12 C13 C14 N1 -172.67(11) . . . . ?
C20 C15 C16 C17 1.5(3) . . . . ?
S1 C15 C16 C17 178.06(15) . . . . ?
C15 C16 C17 C18 -0.9(3) . . . . ?
C16 C17 C18 C19 0.0(3) . . . . ?
C16 C17 C18 C21 179.3(2) . . . . ?
C17 C18 C19 C20 0.3(3) . . . . ?
C21 C18 C19 C20 -179.0(2) . . . . ?
C16 C15 C20 C19 -1.2(3) . . . . ?
S1 C15 C20 C19 -177.71(16) . . . . ?
C18 C19 C20 C15 0.3(3) . . . . ?
C14 C13 C22 O3 -146.99(19) . . . . ?
C7 C13 C22 O3 -25.1(2) . . . . ?
C12 C13 C22 O3 86.1(2) . . . . ?
C14 C13 C22 O4 36.77(17) . . . . ?
C7 C13 C22 O4 158.66(13) . . . . ?
C12 C13 C22 O4 -90.11(15) . . . . ?
C11 C12 C24 C25 -42.95(19) . . . . ?
C13 C12 C24 C25 79.51(18) . . . . ?
C11 C12 C24 C29 135.22(15) . . . . ?
C13 C12 C24 C29 -102.32(16) . . . . ?
C29 C24 C25 C26 -2.7(2) . . . . ?
C12 C24 C25 C26 175.53(15) . . . . ?
C24 C25 C26 C27 0.6(3) . . . . ?
C25 C26 C27 C28 2.2(3) . . . . ?
C25 C26 C27 C30 -176.29(17) . . . . ?
C26 C27 C28 C29 -2.8(3) . . . . ?
C30 C27 C28 C29 175.72(18) . . . . ?
C27 C28 C29 C24 0.6(3) . . . . ?
C25 C24 C29 C28 2.1(2) . . . . ?
C12 C24 C29 C28 -176.21(16) . . . . ?
C26 C27 C30 C32 -30.3(3) . . . . ?
C28 C27 C30 C32 151.3(3) . . . . ?
C26 C27 C30 C31 95.5(3) . . . . ?
C28 C27 C30 C31 -83.0(3) . . . . ?
C6 C1 N1 C14 -23.38(19) . . . . ?
C2 C1 N1 C14 157.69(15) . . . . ?
C6 C1 N1 S1 166.00(12) . . . . ?
C2 C1 N1 S1 -12.9(2) . . . . ?
C13 C14 N1 C1 53.48(16) . . . . ?
C13 C14 N1 S1 -135.57(10) . . . . ?
C6 C7 N2 C8 86.52(16) . . . . ?
C13 C7 N2 C8 -151.07(13) . . . . ?
C6 C7 N2 C11 -150.42(12) . . . . ?
C13 C7 N2 C11 -28.01(14) . . . . ?
C9 C8 N2 C7 144.53(15) . . . . ?
C9 C8 N2 C11 20.99(19) . . . . ?
C10 C11 N2 C7 -123.54(14) . . . . ?
C12 C11 N2 C7 1.73(15) . . . . ?
C10 C11 N2 C8 4.33(17) . . . . ?
C12 C11 N2 C8 129.59(13) . . . . ?
O3 C22 O4 C23 2.6(3) . . . . ?
C13 C22 O4 C23 178.84(15) . . . . ?
C1 N1 S1 O2 -172.02(12) . . . . ?
C14 N1 S1 O2 17.55(13) . . . . ?
C1 N1 S1 O1 -42.41(14) . . . . ?
C14 N1 S1 O1 147.16(11) . . . . ?
C1 N1 S1 C15 73.73(13) . . . . ?
C14 N1 S1 C15 -96.70(12) . . . . ?
C20 C15 S1 O2 119.05(15) . . . . ?
C16 C15 S1 O2 -57.49(15) . . . . ?
C20 C15 S1 O1 -11.15(17) . . . . ?
C16 C15 S1 O1 172.30(14) . . . . ?
C20 C15 S1 N1 -127.64(14) . . . . ?
C16 C15 S1 N1 55.81(15) . . . . ?

_diffrn_measured_fraction_theta_max 1.000
_diffrn_reflns_theta_full        27.50
_diffrn_measured_fraction_theta_full 1.000
_refine_diff_density_max         0.391
_refine_diff_density_min         -0.362
_refine_diff_density_rms         0.054
