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


#######################################################################
#
#                 Cambridge Crystallographic Data Centre
#                                CCDC 
# 
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# 
#  This CIF contains data from an original supplementary publication 
#  deposited with the CCDC, and may include chemical, crystal,   
#  experimental, refinement, atomic coordinates, 
#  anisotropic displacement parameters and molecular geometry data,
#  as required by the journal to which it was submitted. 
# 
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#  fide research purposes only. It may contain copyright material 
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data_jb73y
_database_code_depnum_ccdc_archive 'CCDC 912142'
#TrackingRef 'archive_jb73.cif'
_audit_creation_date             2010-07-22T11:33:29-00:00
_audit_creation_method           'WinGX routine CIF_UPDATE'
_audit_conform_dict_name         cif_core.dic
_audit_conform_dict_version      2.4
_audit_conform_dict_location     ftp://ftp.iucr.org/pub/cif_core.dic
#----------------------------------------------------------------------------#
# CHEMICAL INFORMATION #
#----------------------------------------------------------------------------#
_chemical_name_systematic        
;
?
;
_chemical_formula_moiety         'C19 H22 N2 O4'
_chemical_formula_sum            'C19 H22 N2 O4'
_chemical_formula_weight         342.39
_chemical_compound_source        'synthesis as described'
_chemical_absolute_configuration syn
#----------------------------------------------------------------------------#
# UNIT CELL INFORMATION #
#----------------------------------------------------------------------------#
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_H-M   'C 2'
_symmetry_space_group_name_Hall  'C 2y'
_symmetry_Int_Tables_number      5
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y, -z'
'x+1/2, y+1/2, z'
'-x+1/2, y+1/2, -z'
_cell_length_a                   19.372(8)
_cell_length_b                   6.401(3)
_cell_length_c                   14.653(8)
_cell_angle_alpha                90
_cell_angle_beta                 96.56(5)
_cell_angle_gamma                90
_cell_volume                     1805.2(15)
_cell_formula_units_Z            4
_cell_measurement_temperature    294(2)
_cell_measurement_reflns_used    0
_cell_measurement_theta_min      0
_cell_measurement_theta_max      0
_cell_measurement_wavelength     0.71073
#----------------------------------------------------------------------------#
# CRYSTAL INFORMATION #
#----------------------------------------------------------------------------#
_exptl_crystal_description       prism
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.41
_exptl_crystal_size_mid          0.24
_exptl_crystal_size_min          0.24
_exptl_crystal_density_diffrn    1.26
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             728
_exptl_special_details           
;
?
;
#----------------------------------------------------------------------------#
# ABSORPTION CORRECTION #
#----------------------------------------------------------------------------#
_exptl_absorpt_coefficient_mu    0.089
_exptl_absorpt_correction_type   none
#----------------------------------------------------------------------------#
# DATA COLLECTION #
#----------------------------------------------------------------------------#
_diffrn_source                   'Enraf Nonius FR590'
_diffrn_ambient_temperature      294(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_detector                 'scintillation LiI'
_diffrn_detector_dtime           1.195
_diffrn_orient_matrix_type       
;
x-axis points to radiation source
the matrix is specified in reciprocal space
;
_diffrn_orient_matrix_ub_11      0.09929
_diffrn_orient_matrix_ub_12      -0.093612
_diffrn_orient_matrix_ub_13      -0.011898
_diffrn_orient_matrix_ub_21      -0.004512
_diffrn_orient_matrix_ub_22      -0.03509
_diffrn_orient_matrix_ub_23      0.066231
_diffrn_orient_matrix_ub_31      -0.131188
_diffrn_orient_matrix_ub_32      -0.028519
_diffrn_orient_matrix_ub_33      -0.013972
_diffrn_measurement_device       '\k-geometry diffractometer'
_diffrn_measurement_device_type  'Enraf Nonius CAD4'
_diffrn_measurement_method       'non-profiled omega scans'
_diffrn_standards_number         2
_diffrn_standards_interval_time  60
_diffrn_standards_decay_%        0
loop_
_diffrn_standard_refln_index_h
_diffrn_standard_refln_index_k
_diffrn_standard_refln_index_l
1 1 3
-1 -1 1
_diffrn_reflns_av_R_equivalents  0.1054
_diffrn_reflns_av_unetI/netI     0.0871
_diffrn_reflns_number            3663
_diffrn_reflns_limit_h_min       -23
_diffrn_reflns_limit_h_max       23
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_l_min       0
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_theta_min         1.4
_diffrn_reflns_theta_max         26.03
_diffrn_reflns_theta_full        26.03
_diffrn_measured_fraction_theta_full 0.993
_diffrn_measured_fraction_theta_max 0.993
_reflns_number_total             3522
_reflns_number_gt                2130
_reflns_threshold_expression     >2sigma(I)
#----------------------------------------------------------------------------#
# COMPUTER PROGRAMS USED #
#----------------------------------------------------------------------------#
_computing_data_collection       'CAD4 Express (Enraf Nonius, 1994)'
_computing_cell_refinement       'CAD4 Express (Enraf Nonius, 1994)'
_computing_data_reduction        'XCAD4 (Harms & Wocadlo, 1995)'
_computing_structure_solution    'SHELXS-86 (Sheldrick, 1986)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    'Ortep-3 for Windows (Farrugia, 1997)'
_computing_publication_material  'WinGX publication routines (Farrugia, 1999)'
#----------------------------------------------------------------------------#
# STRUCTURE SOLUTION
#----------------------------------------------------------------------------#
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
#----------------------------------------------------------------------------#
# REFINEMENT INFORMATION #
#----------------------------------------------------------------------------#
_refine_special_details          
;
Refinement of F^2^ against ALL reflections. The weighted R-factor wR and
goodness of fit S are based on F^2^, conventional R-factors R are based
on F, with F set to zero for negative F^2^. The threshold expression of
F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is
not relevant to the choice of reflections for refinement. R-factors based
on F^2^ are statistically about twice as large as those based on F, and R-
factors based on ALL data will be even larger.
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[\s^2^(Fo^2^)+(0.1270P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     SHELXL
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_extinction_coef       0.0030(14)
_refine_ls_number_reflns         3522
_refine_ls_number_parameters     248
_refine_ls_number_restraints     236
_refine_ls_R_factor_all          0.1481
_refine_ls_R_factor_gt           0.0763
_refine_ls_wR_factor_ref         0.2214
_refine_ls_wR_factor_gt          0.1875
_refine_ls_goodness_of_fit_ref   1.017
_refine_ls_restrained_S_all      0.989
_refine_ls_shift/su_max          0
_refine_ls_shift/su_mean         0
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   3(3)
_refine_diff_density_max         0.266
_refine_diff_density_min         -0.218
_refine_diff_density_rms         0.041
#----------------------------------------------------------------------------#
# ATOMIC TYPES, COORDINATES AND THERMAL PARAMETERS #
#----------------------------------------------------------------------------#
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 0 '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 0.006 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
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 0.60147(18) 1.3554(5) 0.2880(2) 0.0618(10) Uani 1 1 d U . .
O7 O 0.51217(17) 0.7677(5) 0.3886(2) 0.0576(9) Uani 1 1 d U . .
O42 O 0.4076(5) 1.1698(15) -0.0240(5) 0.193(4) Uani 1 1 d U A .
O43A O 0.380(2) 1.433(3) 0.0484(9) 0.151(11) Uani 0.55(4) 1 d PU A 1
O43B O 0.3302(14) 1.347(6) 0.0217(19) 0.139(10) Uani 0.45(4) 1 d PU A 2
N1 N 0.55655(17) 1.0487(5) 0.3270(3) 0.0420(9) Uani 1 1 d U . .
N93 N 0.76555(19) 0.9885(6) 0.6331(3) 0.0539(10) Uani 1 1 d U . .
H93 H 0.7998 0.9052 0.6484 0.065 Uiso 1 1 calc R . .
C2 C 0.5560(2) 1.2221(8) 0.2751(3) 0.0481(11) Uani 1 1 d U . .
C3 C 0.4936(3) 1.2539(9) 0.2057(4) 0.0623(13) Uani 1 1 d U . .
H3A H 0.5093 1.315 0.1512 0.075 Uiso 1 1 calc R . .
H3B H 0.4635 1.3554 0.2305 0.075 Uiso 1 1 calc R . .
C4 C 0.4502(2) 1.0625(9) 0.1765(3) 0.0591(13) Uani 1 1 d U . .
H4 H 0.4752 0.9822 0.1337 0.071 Uiso 1 1 calc R . .
C5 C 0.4429(2) 0.9246(9) 0.2598(4) 0.0600(14) Uani 1 1 d U . .
H5A H 0.418 0.9994 0.3034 0.072 Uiso 1 1 calc R . .
H5B H 0.4168 0.7997 0.2408 0.072 Uiso 1 1 calc R . .
C6 C 0.5128(2) 0.8663(7) 0.3036(3) 0.0488(11) Uani 1 1 d U . .
H6 H 0.5354 0.7752 0.2622 0.059 Uiso 1 1 calc R . .
C8 C 0.5821(2) 0.7817(8) 0.4303(4) 0.0536(12) Uani 1 1 d U . .
H8A H 0.6104 0.6739 0.4067 0.064 Uiso 1 1 calc R . .
H8B H 0.5842 0.766 0.4964 0.064 Uiso 1 1 calc R . .
C9 C 0.6078(2) 1.0012(6) 0.4054(3) 0.0420(10) Uani 1 1 d U . .
H9 H 0.6543 0.9916 0.3856 0.05 Uiso 1 1 calc R . .
C41 C 0.3793(3) 1.1184(11) 0.1272(4) 0.0777(17) Uani 1 1 d U A .
H41A H 0.3535 0.9905 0.1125 0.093 Uiso 1 1 calc R . .
H41B H 0.354 1.1987 0.1687 0.093 Uiso 1 1 calc R . .
C42 C 0.3816(4) 1.2385(15) 0.0424(5) 0.095(2) Uani 1 1 d U . .
C43A C 0.380(3) 1.562(5) -0.032(2) 0.197(18) Uani 0.55(4) 1 d PU A 1
H43A H 0.4269 1.6086 -0.0368 0.295 Uiso 0.55(4) 1 calc PR A 1
H43B H 0.3508 1.6809 -0.0265 0.295 Uiso 0.55(4) 1 calc PR A 1
H43C H 0.3635 1.4832 -0.0855 0.295 Uiso 0.55(4) 1 calc PR A 1
C43B C 0.323(2) 1.472(5) -0.0588(19) 0.138(12) Uani 0.45(4) 1 d PU A 2
H43D H 0.367 1.4792 -0.0832 0.207 Uiso 0.45(4) 1 calc PR A 2
H43E H 0.3085 1.6097 -0.0441 0.207 Uiso 0.45(4) 1 calc PR A 2
H43F H 0.2891 1.4103 -0.1036 0.207 Uiso 0.45(4) 1 calc PR A 2
C91 C 0.6081(2) 1.1545(7) 0.4844(3) 0.0466(11) Uani 1 1 d U . .
H91A H 0.609 1.2959 0.4608 0.056 Uiso 1 1 calc R . .
H91B H 0.5657 1.1378 0.513 0.056 Uiso 1 1 calc R . .
C92 C 0.6692(2) 1.1225(6) 0.5550(3) 0.0403(10) Uani 1 1 d U . .
C93 C 0.7153(2) 0.9610(8) 0.5610(3) 0.0496(11) Uani 1 1 d U . .
H93A H 0.7128 0.8473 0.5213 0.06 Uiso 1 1 calc R . .
C94 C 0.7527(2) 1.1698(7) 0.6771(3) 0.0450(11) Uani 1 1 d U . .
C95 C 0.7903(2) 1.2661(9) 0.7517(3) 0.0522(12) Uani 1 1 d U . .
H95 H 0.8299 1.204 0.7818 0.063 Uiso 1 1 calc R . .
C96 C 0.7673(3) 1.4545(10) 0.7798(4) 0.0628(14) Uani 1 1 d U . .
H96 H 0.7914 1.5219 0.8299 0.075 Uiso 1 1 calc R . .
C97 C 0.7081(3) 1.5468(9) 0.7338(4) 0.0626(14) Uani 1 1 d U . .
H97 H 0.6935 1.6753 0.7541 0.075 Uiso 1 1 calc R . .
C98 C 0.6709(2) 1.4548(8) 0.6601(3) 0.0521(12) Uani 1 1 d U . .
H98 H 0.6317 1.5198 0.6304 0.063 Uiso 1 1 calc R . .
C99 C 0.6928(2) 1.2595(7) 0.6297(3) 0.0422(10) Uani 1 1 d U . .
loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
O2 0.067(2) 0.0477(19) 0.066(2) 0.0092(18) -0.0152(17) -0.0184(17)
O7 0.0592(19) 0.0464(18) 0.068(2) 0.0105(18) 0.0088(16) -0.0092(16)
O42 0.258(9) 0.219(8) 0.114(5) 0.038(5) 0.064(5) 0.071(8)
O43A 0.24(3) 0.133(7) 0.070(7) 0.039(6) -0.008(10) 0.050(12)
O43B 0.116(14) 0.20(2) 0.097(12) 0.085(13) 0.011(10) 0.050(14)
N1 0.044(2) 0.0342(18) 0.047(2) 0.0004(16) 0.0011(17) -0.0087(15)
N93 0.048(2) 0.044(2) 0.067(3) 0.0049(19) -0.005(2) 0.0098(18)
C2 0.044(3) 0.055(3) 0.044(3) -0.002(2) -0.002(2) -0.006(2)
C3 0.066(3) 0.064(3) 0.053(3) 0.011(3) -0.009(2) -0.010(3)
C4 0.052(3) 0.073(3) 0.051(3) -0.004(2) -0.003(2) -0.011(2)
C5 0.048(3) 0.070(4) 0.061(3) 0.000(3) -0.002(2) -0.015(2)
C6 0.051(3) 0.041(2) 0.054(3) -0.006(2) 0.008(2) -0.008(2)
C8 0.055(3) 0.041(2) 0.065(3) 0.009(2) 0.006(2) 0.001(2)
C9 0.039(2) 0.034(2) 0.052(2) 0.0013(19) 0.0023(19) 0.0030(18)
C41 0.060(3) 0.104(5) 0.063(3) 0.005(3) -0.017(3) -0.009(3)
C42 0.077(4) 0.140(7) 0.064(4) 0.014(4) -0.014(3) 0.006(4)
C43A 0.30(5) 0.175(19) 0.122(18) 0.078(17) 0.07(3) 0.11(3)
C43B 0.15(2) 0.16(2) 0.110(16) 0.067(16) 0.026(15) 0.050(17)
C91 0.046(2) 0.043(2) 0.049(3) 0.000(2) 0.000(2) 0.013(2)
C92 0.038(2) 0.042(2) 0.041(2) 0.0045(19) 0.0028(18) 0.0042(19)
C93 0.044(2) 0.046(3) 0.057(3) 0.000(2) -0.003(2) 0.009(2)
C94 0.044(2) 0.042(2) 0.049(3) 0.010(2) 0.004(2) -0.001(2)
C95 0.044(2) 0.067(3) 0.043(2) 0.010(2) -0.003(2) 0.002(2)
C96 0.060(3) 0.076(4) 0.051(3) -0.013(3) 0.004(2) -0.001(3)
C97 0.071(3) 0.052(3) 0.063(3) -0.014(3) 0.003(3) 0.008(3)
C98 0.053(3) 0.052(3) 0.050(3) 0.003(2) 0.001(2) 0.013(2)
C99 0.042(2) 0.046(2) 0.039(2) 0.005(2) 0.0043(19) 0.006(2)
#----------------------------------------------------------------------------#
# MOLECULAR GEOMETRY #
#----------------------------------------------------------------------------#
_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 C2 1.226(5) . ?
O7 C6 1.398(6) . ?
O7 C8 1.424(6) . ?
O42 C42 1.228(10) . ?
O43A C42 1.246(18) . ?
O43A C43A 1.44(2) . ?
O43B C42 1.225(16) . ?
O43B C43B 1.42(3) . ?
N1 C2 1.345(6) . ?
N1 C6 1.460(6) . ?
N1 C9 1.462(6) . ?
N93 C94 1.364(6) . ?
N93 C93 1.364(6) . ?
C2 C3 1.501(6) . ?
C3 C4 1.519(7) . ?
C4 C41 1.520(7) . ?
C4 C5 1.527(7) . ?
C5 C6 1.478(6) . ?
C8 C9 1.548(6) . ?
C9 C91 1.517(6) . ?
C41 C42 1.466(9) . ?
C91 C92 1.495(6) . ?
C92 C93 1.361(6) . ?
C92 C99 1.436(6) . ?
C94 C95 1.388(6) . ?
C94 C99 1.404(6) . ?
C95 C96 1.365(7) . ?
C96 C97 1.394(7) . ?
C97 C98 1.361(7) . ?
C98 C99 1.409(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
C6 O7 C8 104.4(3) . . ?
C42 O43A C43A 121.0(17) . . ?
C42 O43B C43B 121.6(17) . . ?
C2 N1 C6 124.0(4) . . ?
C2 N1 C9 125.2(4) . . ?
C6 N1 C9 110.0(3) . . ?
C94 N93 C93 108.8(4) . . ?
O2 C2 N1 121.9(4) . . ?
O2 C2 C3 121.2(4) . . ?
N1 C2 C3 116.7(4) . . ?
C2 C3 C4 117.3(5) . . ?
C3 C4 C41 112.7(5) . . ?
C3 C4 C5 109.8(4) . . ?
C41 C4 C5 110.8(4) . . ?
C6 C5 C4 109.2(4) . . ?
O7 C6 N1 102.5(4) . . ?
O7 C6 C5 113.6(4) . . ?
N1 C6 C5 112.2(4) . . ?
O7 C8 C9 105.8(4) . . ?
N1 C9 C91 114.1(3) . . ?
N1 C9 C8 99.5(3) . . ?
C91 C9 C8 112.4(4) . . ?
C42 C41 C4 114.4(5) . . ?
O43B C42 O42 113.7(15) . . ?
O43B C42 O43A 54.9(10) . . ?
O42 C42 O43A 115.4(14) . . ?
O43B C42 C41 113.9(9) . . ?
O42 C42 C41 122.7(9) . . ?
O43A C42 C41 117.4(9) . . ?
C92 C91 C9 111.9(4) . . ?
C93 C92 C99 105.4(4) . . ?
C93 C92 C91 127.6(4) . . ?
C99 C92 C91 127.0(4) . . ?
C92 C93 N93 110.9(4) . . ?
N93 C94 C95 130.0(4) . . ?
N93 C94 C99 107.5(4) . . ?
C95 C94 C99 122.5(4) . . ?
C96 C95 C94 118.1(4) . . ?
C95 C96 C97 120.5(5) . . ?
C98 C97 C96 122.1(5) . . ?
C97 C98 C99 118.9(4) . . ?
C94 C99 C98 117.9(4) . . ?
C94 C99 C92 107.5(4) . . ?
C98 C99 C92 134.6(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
C6 N1 C2 O2 -166.7(4) . . . . ?
C9 N1 C2 O2 2.7(7) . . . . ?
C6 N1 C2 C3 18.4(7) . . . . ?
C9 N1 C2 C3 -172.2(4) . . . . ?
O2 C2 C3 C4 164.4(5) . . . . ?
N1 C2 C3 C4 -20.7(7) . . . . ?
C2 C3 C4 C41 164.6(5) . . . . ?
C2 C3 C4 C5 40.5(6) . . . . ?
C3 C4 C5 C6 -57.2(6) . . . . ?
C41 C4 C5 C6 177.6(5) . . . . ?
C8 O7 C6 N1 -41.9(4) . . . . ?
C8 O7 C6 C5 -163.2(4) . . . . ?
C2 N1 C6 O7 -159.0(4) . . . . ?
C9 N1 C6 O7 30.1(5) . . . . ?
C2 N1 C6 C5 -36.9(6) . . . . ?
C9 N1 C6 C5 152.3(4) . . . . ?
C4 C5 C6 O7 170.5(4) . . . . ?
C4 C5 C6 N1 54.8(5) . . . . ?
C6 O7 C8 C9 39.1(4) . . . . ?
C2 N1 C9 C91 63.0(6) . . . . ?
C6 N1 C9 C91 -126.3(4) . . . . ?
C2 N1 C9 C8 -177.2(4) . . . . ?
C6 N1 C9 C8 -6.5(4) . . . . ?
O7 C8 C9 N1 -19.1(4) . . . . ?
O7 C8 C9 C91 102.0(4) . . . . ?
C3 C4 C41 C42 60.6(8) . . . . ?
C5 C4 C41 C42 -175.8(6) . . . . ?
C43B O43B C42 O42 -32(4) . . . . ?
C43B O43B C42 O43A 73(2) . . . . ?
C43B O43B C42 C41 -179(2) . . . . ?
C43A O43A C42 O43B -77(2) . . . . ?
C43A O43A C42 O42 25(3) . . . . ?
C43A O43A C42 C41 -178.4(19) . . . . ?
C4 C41 C42 O43B -154(3) . . . . ?
C4 C41 C42 O42 62.0(11) . . . . ?
C4 C41 C42 O43A -93(2) . . . . ?
N1 C9 C91 C92 -169.6(4) . . . . ?
C8 C9 C91 C92 78.1(5) . . . . ?
C9 C91 C92 C93 -10.0(6) . . . . ?
C9 C91 C92 C99 168.2(4) . . . . ?
C99 C92 C93 N93 -0.4(5) . . . . ?
C91 C92 C93 N93 178.2(4) . . . . ?
C94 N93 C93 C92 0.8(5) . . . . ?
C93 N93 C94 C95 -177.7(5) . . . . ?
C93 N93 C94 C99 -0.9(5) . . . . ?
N93 C94 C95 C96 176.8(5) . . . . ?
C99 C94 C95 C96 0.4(7) . . . . ?
C94 C95 C96 C97 -0.4(7) . . . . ?
C95 C96 C97 C98 0.0(9) . . . . ?
C96 C97 C98 C99 0.4(8) . . . . ?
N93 C94 C99 C98 -177.1(4) . . . . ?
C95 C94 C99 C98 0.0(6) . . . . ?
N93 C94 C99 C92 0.6(5) . . . . ?
C95 C94 C99 C92 177.8(4) . . . . ?
C97 C98 C99 C94 -0.4(6) . . . . ?
C97 C98 C99 C92 -177.4(5) . . . . ?
C93 C92 C99 C94 -0.2(5) . . . . ?
C91 C92 C99 C94 -178.7(4) . . . . ?
C93 C92 C99 C98 177.0(5) . . . . ?
C91 C92 C99 C98 -1.5(8) . . . . ?


data_jb84
_database_code_depnum_ccdc_archive 'CCDC 912143'
#TrackingRef 'archive_jb84.cif'
_audit_creation_date             2010-06-10T10:00:53-00:00
_audit_creation_method           'WinGX routine CIF_UPDATE'
_audit_conform_dict_name         cif_core.dic
_audit_conform_dict_version      2.3
_audit_conform_dict_location     ftp://ftp.iucr.org/pub/cif_core.dic
#----------------------------------------------------------------------------#
# CHEMICAL INFORMATION #
#----------------------------------------------------------------------------#
_chemical_name_systematic        
;
?
;
_chemical_formula_moiety         'C24 H26 N2 O5 S1'
_chemical_formula_sum            'C24 H26 N2 O5 S'
_chemical_formula_weight         454.53
_chemical_compound_source        'synthesis as described'
_chemical_absolute_configuration ad
#----------------------------------------------------------------------------#
# UNIT CELL INFORMATION #
#----------------------------------------------------------------------------#
_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_H-M   'P 21 21 21'
_symmetry_space_group_name_Hall  'P 2ac 2ab'
_symmetry_Int_Tables_number      19
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'x+1/2, -y+1/2, -z'
'-x, y+1/2, -z+1/2'
_cell_length_a                   7.490(3)
_cell_length_b                   16.436(18)
_cell_length_c                   17.817(11)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     2193.4(3)
_cell_formula_units_Z            4
_cell_measurement_temperature    294(2)
_cell_measurement_reflns_used    25
_cell_measurement_theta_min      10.6
_cell_measurement_theta_max      21.8
_cell_measurement_wavelength     0.71073
#----------------------------------------------------------------------------#
# CRYSTAL INFORMATION #
#----------------------------------------------------------------------------#
_exptl_crystal_description       prism
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.41
_exptl_crystal_size_mid          0.29
_exptl_crystal_size_min          0.12
_exptl_crystal_density_diffrn    1.376
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             960
_exptl_special_details           
;
?
;
#----------------------------------------------------------------------------#
# ABSORPTION CORRECTION #
#----------------------------------------------------------------------------#
_exptl_absorpt_coefficient_mu    0.187
_exptl_absorpt_correction_type   refdelf
_exptl_absorpt_process_details   
;
Walker, N. & Stuart, D (1983) Acta. Cryst. A39, 158-166
;
_exptl_absorpt_correction_T_min  0.9053
_exptl_absorpt_correction_T_max  0.9597
#----------------------------------------------------------------------------#
# DATA COLLECTION #
#----------------------------------------------------------------------------#
_diffrn_source                   'Enraf Nonius FR590'
_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_detector                 'scintillation LiI'
_diffrn_detector_dtime           1.195
_diffrn_orient_matrix_type       
;
x-axis points to radiation source
the matrix is specified in reciprocal space
;
_diffrn_orient_matrix_ub_11      0.001695
_diffrn_orient_matrix_ub_12      -0.038368
_diffrn_orient_matrix_ub_13      0.043653
_diffrn_orient_matrix_ub_21      0.005492
_diffrn_orient_matrix_ub_22      0.047186
_diffrn_orient_matrix_ub_23      0.035275
_diffrn_orient_matrix_ub_31      -0.133386
_diffrn_orient_matrix_ub_32      0.001376
_diffrn_orient_matrix_ub_33      0.001938
_diffrn_measurement_device       '\k-geometry diffractometer'
_diffrn_measurement_device_type  'Enraf Nonius CAD4'
_diffrn_measurement_method       'non-profiled omega scans'
_diffrn_standards_number         0
_diffrn_standards_interval_time  60
_diffrn_standards_decay_%        0
_diffrn_reflns_av_R_equivalents  0
_diffrn_reflns_av_unetI/netI     0.2342
_diffrn_reflns_number            2460
_diffrn_reflns_limit_h_min       0
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       0
_diffrn_reflns_limit_k_max       20
_diffrn_reflns_limit_l_min       0
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_theta_min         1.69
_diffrn_reflns_theta_max         25.97
_diffrn_reflns_theta_full        25.97
_diffrn_measured_fraction_theta_full 1
_diffrn_measured_fraction_theta_max 1
_reflns_number_total             2460
_reflns_number_gt                772
_reflns_threshold_expression     >2sigma(I)
#----------------------------------------------------------------------------#
# COMPUTER PROGRAMS USED #
#----------------------------------------------------------------------------#
_computing_data_collection       'CAD4 Express (Enraf Nonius, 1994)'
_computing_cell_refinement       'CAD4 Express (Enraf Nonius, 1994)'
_computing_data_reduction        'XCAD4 (Harms & Wocadlo, 1995)'
_computing_structure_solution    'SHELXS-86 (Sheldrick, 1986)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    'Ortep-3 for Windows (Farrugia, 1997)'
_computing_publication_material  'WinGX publication routines (Farrugia, 1999)'
#----------------------------------------------------------------------------#
# REFINEMENT INFORMATION #
#----------------------------------------------------------------------------#
_refine_special_details          
;
Refinement of F^2^ against ALL reflections. The weighted R-factor wR and
goodness of fit S are based on F^2^, conventional R-factors R are based
on F, with F set to zero for negative F^2^. The threshold expression of
F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is
not relevant to the choice of reflections for refinement. R-factors based
on F^2^ are statistically about twice as large as those based on F, and R-
factors based on ALL data will be even larger.
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[\s^2^(Fo^2^)+(0.0362P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    calcd
_refine_ls_extinction_method     none
_refine_ls_number_reflns         2460
_refine_ls_number_parameters     290
_refine_ls_number_restraints     91
_refine_ls_R_factor_all          0.2321
_refine_ls_R_factor_gt           0.0737
_refine_ls_wR_factor_ref         0.1463
_refine_ls_wR_factor_gt          0.1141
_refine_ls_goodness_of_fit_ref   0.859
_refine_ls_restrained_S_all      0.85
_refine_ls_shift/su_max          0
_refine_ls_shift/su_mean         0
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.0(3)
_refine_diff_density_max         0.216
_refine_diff_density_min         -0.29
_refine_diff_density_rms         0.057
#----------------------------------------------------------------------------#
# ATOMIC TYPES, COORDINATES AND THERMAL PARAMETERS #
#----------------------------------------------------------------------------#
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 0 '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 0.006 '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'
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
S1 S 0.3238(3) 0.8304(2) 0.82260(19) 0.0670(9) Uani 1 1 d U . .
O2 O 1.0907(8) 0.4965(5) 0.9220(4) 0.095(3) Uani 1 1 d U . .
O11 O 0.2248(9) 0.8510(5) 0.8907(5) 0.086(3) Uani 1 1 d U . .
O12 O 0.2473(8) 0.8427(5) 0.7495(4) 0.083(2) Uani 1 1 d U . .
O42 O 0.6423(14) 0.2396(6) 0.9975(5) 0.117(4) Uani 1 1 d U . .
O43 O 0.5373(10) 0.3155(5) 1.0877(5) 0.086(3) Uani 1 1 d U . .
N1 N 0.8487(9) 0.5723(6) 0.9237(5) 0.056(2) Uani 1 1 d U . .
N11 N 0.3673(9) 0.7310(5) 0.8289(5) 0.058(2) Uani 1 1 d U . .
C2 C 0.9269(13) 0.5006(8) 0.9292(6) 0.063(3) Uani 1 1 d U . .
C3 C 0.8162(12) 0.4273(6) 0.9466(6) 0.060(3) Uani 1 1 d U . .
H3A H 0.8739 0.3977 0.987 0.072 Uiso 1 1 calc R . .
H3B H 0.8163 0.3922 0.9029 0.072 Uiso 1 1 calc R . .
C4 C 0.6254(12) 0.4425(6) 0.9688(5) 0.049(3) Uani 1 1 d U . .
H4 H 0.6239 0.4628 1.0206 0.059 Uiso 1 1 calc R . .
C5 C 0.5507(11) 0.5077(6) 0.9185(5) 0.048(3) Uani 1 1 d U . .
H5A H 0.4253 0.5162 0.9296 0.057 Uiso 1 1 calc R . .
H5B H 0.5611 0.4912 0.8664 0.057 Uiso 1 1 calc R . .
C6 C 0.6540(12) 0.5855(6) 0.9314(5) 0.051(2) Uani 1 1 d U . .
H6 H 0.6317 0.6024 0.9834 0.061 Uiso 1 1 calc R . .
C7 C 0.6204(12) 0.6600(7) 0.8812(5) 0.049(2) Uani 1 1 d U . .
C8 C 0.7880(12) 0.7076(6) 0.8922(6) 0.061(3) Uani 1 1 d U . .
H8A H 0.7802 0.7402 0.9375 0.073 Uiso 1 1 calc R . .
H8B H 0.8076 0.7438 0.8499 0.073 Uiso 1 1 calc R . .
C9 C 0.9433(12) 0.6454(7) 0.8986(6) 0.074(3) Uani 1 1 d U . .
H9A H 1.0011 0.6368 0.8505 0.088 Uiso 1 1 calc R . .
H9B H 1.0316 0.6628 0.935 0.088 Uiso 1 1 calc R . .
C10 C 0.4436(12) 0.7055(7) 0.9014(6) 0.064(3) Uani 1 1 d U . .
H10A H 0.3621 0.6696 0.9278 0.077 Uiso 1 1 calc R . .
H10B H 0.468 0.7524 0.9328 0.077 Uiso 1 1 calc R . .
C12 C 0.4520(12) 0.6849(8) 0.7697(6) 0.054(3) Uani 1 1 d U . .
C13 C 0.3950(12) 0.6840(7) 0.6978(6) 0.063(3) Uani 1 1 d U . .
H13 H 0.3025 0.7168 0.6806 0.076 Uiso 1 1 calc R . .
C14 C 0.4868(14) 0.6295(6) 0.6514(6) 0.073(3) Uani 1 1 d U . .
H14 H 0.4503 0.624 0.6018 0.087 Uiso 1 1 calc R . .
C15 C 0.6284(12) 0.5837(6) 0.6761(6) 0.059(3) Uani 1 1 d U . .
H15 H 0.6912 0.5507 0.6429 0.071 Uiso 1 1 calc R . .
C16 C 0.6766(14) 0.5875(7) 0.7516(5) 0.065(3) Uani 1 1 d U . .
H16 H 0.7667 0.5543 0.7704 0.078 Uiso 1 1 calc R . .
C17 C 0.5865(11) 0.6424(6) 0.7988(5) 0.048(3) Uani 1 1 d U . .
C18 C 0.5311(11) 0.8784(6) 0.8271(7) 0.056(3) Uani 1 1 d U . .
C19 C 0.5872(15) 0.9113(8) 0.8899(7) 0.074(4) Uani 1 1 d U . .
H19 H 0.5152 0.9083 0.9323 0.089 Uiso 1 1 calc R . .
C20 C 0.7509(16) 0.9505(7) 0.8948(8) 0.085(4) Uani 1 1 d U . .
H20 H 0.7916 0.9705 0.9406 0.103 Uiso 1 1 calc R . .
C21 C 0.8533(14) 0.9593(8) 0.8299(8) 0.092(4) Uani 1 1 d U . .
H21 H 0.963 0.9858 0.8317 0.111 Uiso 1 1 calc R . .
C22 C 0.7901(17) 0.9286(9) 0.7634(7) 0.103(5) Uani 1 1 d U . .
H22 H 0.8582 0.9334 0.72 0.124 Uiso 1 1 calc R . .
C23 C 0.6323(14) 0.8920(7) 0.7608(6) 0.068(3) Uani 1 1 d U . .
H23 H 0.5871 0.875 0.7148 0.082 Uiso 1 1 calc R . .
C41 C 0.5113(13) 0.3655(6) 0.9651(6) 0.069(3) Uani 1 1 d U . .
H41A H 0.3883 0.3795 0.9761 0.082 Uiso 1 1 calc R . .
H41B H 0.5155 0.3439 0.9144 0.082 Uiso 1 1 calc R . .
C42 C 0.5714(17) 0.3022(8) 1.0181(8) 0.070(4) Uani 1 1 d U . .
C43 C 0.5945(14) 0.2512(8) 1.1413(6) 0.113(5) Uani 1 1 d U . .
H43A H 0.5757 0.1987 1.1191 0.169 Uiso 1 1 calc R . .
H43B H 0.5258 0.2555 1.1866 0.169 Uiso 1 1 calc R . .
H43C H 0.7189 0.258 1.1527 0.169 Uiso 1 1 calc R . .
loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
S1 0.0394(14) 0.081(2) 0.080(2) -0.006(2) -0.0133(19) 0.0178(17)
O2 0.027(3) 0.139(8) 0.120(8) 0.008(7) 0.010(5) 0.023(5)
O11 0.049(4) 0.104(7) 0.104(5) -0.010(6) 0.017(4) 0.032(5)
O12 0.065(5) 0.084(6) 0.099(5) 0.004(5) -0.048(4) 0.022(5)
O42 0.140(10) 0.096(8) 0.114(7) -0.023(6) -0.010(7) 0.038(7)
O43 0.070(5) 0.109(7) 0.078(5) 0.002(5) 0.000(5) -0.002(5)
N1 0.022(4) 0.075(5) 0.071(6) -0.006(6) 0.004(5) 0.008(4)
N11 0.037(5) 0.076(5) 0.063(5) 0.008(5) -0.007(5) 0.012(4)
C2 0.033(5) 0.084(7) 0.074(9) -0.015(8) 0.010(6) 0.015(5)
C3 0.039(5) 0.072(7) 0.069(8) -0.010(7) -0.002(6) 0.015(5)
C4 0.038(5) 0.061(6) 0.049(6) -0.007(5) 0.000(5) 0.008(5)
C5 0.029(5) 0.074(7) 0.041(7) 0.005(6) -0.007(5) 0.003(5)
C6 0.032(5) 0.066(6) 0.056(6) -0.006(6) 0.003(6) 0.009(4)
C7 0.028(4) 0.061(6) 0.059(6) -0.005(5) -0.006(5) -0.001(4)
C8 0.045(5) 0.085(7) 0.052(7) 0.000(6) 0.000(6) -0.007(5)
C9 0.036(5) 0.110(9) 0.074(8) 0.008(9) -0.002(6) -0.009(6)
C10 0.046(5) 0.088(9) 0.057(6) -0.003(6) 0.008(6) 0.022(6)
C12 0.022(5) 0.084(8) 0.054(5) 0.008(6) -0.005(4) -0.002(5)
C13 0.047(6) 0.079(9) 0.064(6) 0.002(6) -0.023(5) 0.016(6)
C14 0.061(7) 0.089(10) 0.069(8) -0.013(6) -0.006(6) -0.012(6)
C15 0.041(6) 0.080(8) 0.056(6) -0.018(7) 0.010(7) 0.000(5)
C16 0.043(6) 0.086(8) 0.066(6) -0.001(7) 0.014(6) 0.000(6)
C17 0.028(5) 0.075(8) 0.043(5) 0.006(5) 0.008(4) -0.009(5)
C18 0.027(4) 0.077(7) 0.063(6) 0.012(7) -0.012(5) 0.013(4)
C19 0.057(7) 0.102(11) 0.064(6) -0.010(8) -0.007(6) 0.010(7)
C20 0.077(8) 0.081(10) 0.099(9) -0.033(9) -0.023(7) 0.009(7)
C21 0.042(7) 0.096(10) 0.138(11) -0.014(11) -0.013(7) -0.001(7)
C22 0.064(8) 0.151(15) 0.094(9) 0.009(11) 0.020(8) -0.025(8)
C23 0.059(7) 0.091(10) 0.055(6) 0.007(7) -0.021(6) 0.000(6)
C41 0.050(6) 0.075(7) 0.081(8) -0.001(7) -0.006(7) -0.005(6)
C42 0.059(8) 0.065(8) 0.086(8) 0.000(7) 0.006(8) 0.002(7)
C43 0.074(9) 0.158(13) 0.106(10) 0.058(9) -0.033(8) -0.042(9)
#----------------------------------------------------------------------------#
# MOLECULAR GEOMETRY #
#----------------------------------------------------------------------------#
_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
S1 O12 1.437(6) . ?
S1 O11 1.461(7) . ?
S1 N11 1.671(8) . ?
S1 C18 1.744(9) . ?
O2 C2 1.235(9) . ?
O42 C42 1.214(12) . ?
O43 C42 1.286(13) . ?
O43 C43 1.486(11) . ?
N1 C2 1.320(12) . ?
N1 C9 1.466(12) . ?
N1 C6 1.481(11) . ?
N11 C12 1.446(11) . ?
N11 C10 1.473(11) . ?
C2 C3 1.495(13) . ?
C3 C4 1.504(12) . ?
C4 C5 1.505(11) . ?
C4 C41 1.529(13) . ?
C5 C6 1.513(12) . ?
C6 C7 1.537(13) . ?
C7 C8 1.492(12) . ?
C7 C17 1.519(12) . ?
C7 C10 1.563(12) . ?
C8 C9 1.553(12) . ?
C12 C17 1.331(12) . ?
C12 C13 1.349(11) . ?
C13 C14 1.400(12) . ?
C14 C15 1.372(12) . ?
C15 C16 1.394(12) . ?
C16 C17 1.406(12) . ?
C18 C19 1.312(14) . ?
C18 C23 1.420(13) . ?
C19 C20 1.388(14) . ?
C20 C21 1.395(14) . ?
C21 C22 1.373(14) . ?
C22 C23 1.327(14) . ?
C41 C42 1.476(14) . ?
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
O12 S1 O11 121.2(4) . . ?
O12 S1 N11 106.1(5) . . ?
O11 S1 N11 105.7(5) . . ?
O12 S1 C18 109.4(6) . . ?
O11 S1 C18 108.0(6) . . ?
N11 S1 C18 105.4(4) . . ?
C42 O43 C43 116.2(11) . . ?
C2 N1 C9 122.7(8) . . ?
C2 N1 C6 124.2(10) . . ?
C9 N1 C6 112.6(9) . . ?
C12 N11 C10 108.7(7) . . ?
C12 N11 S1 123.3(7) . . ?
C10 N11 S1 114.4(7) . . ?
O2 C2 N1 118.8(12) . . ?
O2 C2 C3 121.9(12) . . ?
N1 C2 C3 119.2(9) . . ?
C2 C3 C4 116.6(9) . . ?
C3 C4 C5 108.4(9) . . ?
C3 C4 C41 112.4(9) . . ?
C5 C4 C41 110.8(8) . . ?
C4 C5 C6 108.7(8) . . ?
N1 C6 C5 111.5(9) . . ?
N1 C6 C7 102.9(9) . . ?
C5 C6 C7 120.1(8) . . ?
C8 C7 C17 111.5(8) . . ?
C8 C7 C6 101.8(8) . . ?
C17 C7 C6 116.0(10) . . ?
C8 C7 C10 115.6(9) . . ?
C17 C7 C10 99.9(8) . . ?
C6 C7 C10 112.7(8) . . ?
C7 C8 C9 107.1(8) . . ?
N1 C9 C8 101.5(7) . . ?
N11 C10 C7 105.2(8) . . ?
C17 C12 C13 127.1(11) . . ?
C17 C12 N11 108.8(9) . . ?
C13 C12 N11 124.0(10) . . ?
C12 C13 C14 114.3(10) . . ?
C15 C14 C13 122.7(11) . . ?
C14 C15 C16 119.0(11) . . ?
C15 C16 C17 118.7(11) . . ?
C12 C17 C16 117.9(10) . . ?
C12 C17 C7 113.8(10) . . ?
C16 C17 C7 128.3(10) . . ?
C19 C18 C23 118.2(10) . . ?
C19 C18 S1 120.7(10) . . ?
C23 C18 S1 120.5(9) . . ?
C18 C19 C20 121.9(13) . . ?
C19 C20 C21 118.7(13) . . ?
C22 C21 C20 119.2(11) . . ?
C23 C22 C21 120.2(13) . . ?
C22 C23 C18 121.2(12) . . ?
C42 C41 C4 112.7(9) . . ?
O42 C42 O43 121.5(14) . . ?
O42 C42 C41 122.6(14) . . ?
O43 C42 C41 115.9(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
O12 S1 N11 C12 45.3(8) . . . . ?
O11 S1 N11 C12 175.1(7) . . . . ?
C18 S1 N11 C12 -70.7(9) . . . . ?
O12 S1 N11 C10 -178.7(6) . . . . ?
O11 S1 N11 C10 -48.9(7) . . . . ?
C18 S1 N11 C10 65.3(8) . . . . ?
C9 N1 C2 O2 9.3(17) . . . . ?
C6 N1 C2 O2 -179.8(10) . . . . ?
C9 N1 C2 C3 -172.9(10) . . . . ?
C6 N1 C2 C3 -2.1(17) . . . . ?
O2 C2 C3 C4 168.4(10) . . . . ?
N1 C2 C3 C4 -9.3(16) . . . . ?
C2 C3 C4 C5 41.9(13) . . . . ?
C2 C3 C4 C41 164.7(9) . . . . ?
C3 C4 C5 C6 -63.2(11) . . . . ?
C41 C4 C5 C6 173.1(8) . . . . ?
C2 N1 C6 C5 -20.4(15) . . . . ?
C9 N1 C6 C5 151.3(9) . . . . ?
C2 N1 C6 C7 -150.4(10) . . . . ?
C9 N1 C6 C7 21.3(11) . . . . ?
C4 C5 C6 N1 52.8(11) . . . . ?
C4 C5 C6 C7 173.2(8) . . . . ?
N1 C6 C7 C8 -34.6(10) . . . . ?
C5 C6 C7 C8 -159.1(8) . . . . ?
N1 C6 C7 C17 86.7(10) . . . . ?
C5 C6 C7 C17 -37.8(12) . . . . ?
N1 C6 C7 C10 -159.0(8) . . . . ?
C5 C6 C7 C10 76.4(12) . . . . ?
C17 C7 C8 C9 -87.6(12) . . . . ?
C6 C7 C8 C9 36.7(10) . . . . ?
C10 C7 C8 C9 159.2(9) . . . . ?
C2 N1 C9 C8 172.7(10) . . . . ?
C6 N1 C9 C8 0.9(11) . . . . ?
C7 C8 C9 N1 -23.9(11) . . . . ?
C12 N11 C10 C7 16.8(10) . . . . ?
S1 N11 C10 C7 -125.4(7) . . . . ?
C8 C7 C10 N11 101.8(10) . . . . ?
C17 C7 C10 N11 -18.0(10) . . . . ?
C6 C7 C10 N11 -141.7(9) . . . . ?
C10 N11 C12 C17 -7.9(11) . . . . ?
S1 N11 C12 C17 130.2(8) . . . . ?
C10 N11 C12 C13 169.5(11) . . . . ?
S1 N11 C12 C13 -52.4(14) . . . . ?
C17 C12 C13 C14 2.5(18) . . . . ?
N11 C12 C13 C14 -174.4(9) . . . . ?
C12 C13 C14 C15 -3.0(16) . . . . ?
C13 C14 C15 C16 4.2(16) . . . . ?
C14 C15 C16 C17 -4.4(16) . . . . ?
C13 C12 C17 C16 -2.9(18) . . . . ?
N11 C12 C17 C16 174.3(8) . . . . ?
C13 C12 C17 C7 177.7(11) . . . . ?
N11 C12 C17 C7 -5.0(12) . . . . ?
C15 C16 C17 C12 3.8(16) . . . . ?
C15 C16 C17 C7 -177.0(10) . . . . ?
C8 C7 C17 C12 -108.0(10) . . . . ?
C6 C7 C17 C12 136.0(10) . . . . ?
C10 C7 C17 C12 14.6(12) . . . . ?
C8 C7 C17 C16 72.7(14) . . . . ?
C6 C7 C17 C16 -43.2(13) . . . . ?
C10 C7 C17 C16 -164.6(9) . . . . ?
O12 S1 C18 C19 146.0(10) . . . . ?
O11 S1 C18 C19 12.3(11) . . . . ?
N11 S1 C18 C19 -100.3(10) . . . . ?
O12 S1 C18 C23 -25.7(10) . . . . ?
O11 S1 C18 C23 -159.4(9) . . . . ?
N11 S1 C18 C23 88.0(10) . . . . ?
C23 C18 C19 C20 -7.5(17) . . . . ?
S1 C18 C19 C20 -179.4(10) . . . . ?
C18 C19 C20 C21 4(2) . . . . ?
C19 C20 C21 C22 -1(2) . . . . ?
C20 C21 C22 C23 1(2) . . . . ?
C21 C22 C23 C18 -5(2) . . . . ?
C19 C18 C23 C22 7.9(17) . . . . ?
S1 C18 C23 C22 179.9(10) . . . . ?
C3 C4 C41 C42 63.1(13) . . . . ?
C5 C4 C41 C42 -175.5(10) . . . . ?
C43 O43 C42 O42 1.8(19) . . . . ?
C43 O43 C42 C41 178.9(9) . . . . ?
C4 C41 C42 O42 -109.8(14) . . . . ?
C4 C41 C42 O43 73.1(14) . . . . ?