# Supplementary Material (ESI) for Chemical Communications
# This journal is © The Royal Society of Chemistry 2007

data_global
_journal_coden_Cambridge         0182
_audit_update_record             
;
2007-11-05 # Formatted by publCIF
;

_publ_contact_author             'Jorgensen, Karl Anker'
_publ_contact_author_email       kaj@chem.au.dk

loop_
_publ_author_name
'K. Jorgensen'
'Jose Aleman'
'Kim Frisch'
'Christian Borch Jacobsen'
'Jacob Overgaard'

_publ_requested_journal          'Chemical Communications'

_publ_section_title              
;
Organocatalytic Asymmetric Vinylogous Addition to
Quinones - Formation of Optically Active alpha-Aryl Ketones
;

data_07jo0045_0m
_database_code_depnum_ccdc_archive 'CCDC 666377'

_audit_creation_date             2007-10-24T15:13:13-00:00
_audit_creation_method           'WinGX routine CIF_UPDATE'

#----------------------------------------------------------------------------#
# CHEMICAL INFORMATION #
#----------------------------------------------------------------------------#

_chemical_name_systematic        
;
?
;
_chemical_formula_moiety         'C26 H16 N2 O2 S, C3 H6 O'
_chemical_formula_sum            'C29 H22 N2 O3 S'
_chemical_formula_weight         478.55
_chemical_compound_source        'synthesis as described'

#----------------------------------------------------------------------------#
# UNIT CELL INFORMATION #
#----------------------------------------------------------------------------#

_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_H-M   'P 1 21/n 1'
_symmetry_space_group_name_Hall  '-P 2yn'
_symmetry_Int_Tables_number      14
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -y-1/2, z-1/2'

_cell_length_a                   8.6648(7)
_cell_length_b                   13.1089(10)
_cell_length_c                   20.6600(15)
_cell_angle_alpha                90
_cell_angle_beta                 90.731(3)
_cell_angle_gamma                90
_cell_volume                     2346.5(3)
_cell_formula_units_Z            4
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    2435
_cell_measurement_theta_min      2.51
_cell_measurement_theta_max      23.86
_cell_measurement_wavelength     0.71073

#----------------------------------------------------------------------------#
# CRYSTAL INFORMATION #
#----------------------------------------------------------------------------#

_exptl_crystal_description       block
_exptl_crystal_colour            yellow
_exptl_crystal_size_max          0.1
_exptl_crystal_size_mid          0.08
_exptl_crystal_size_min          0.05
_exptl_crystal_density_diffrn    1.355
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1000
_exptl_special_details           
;
The crystal was tiny and it was not possible to collect data to higher angle.
;

#----------------------------------------------------------------------------#
# ABSORPTION CORRECTION #
#----------------------------------------------------------------------------#

_exptl_absorpt_coefficient_mu    0.173
_exptl_absorpt_correction_type   none

#----------------------------------------------------------------------------#
# DATA COLLECTION #
#----------------------------------------------------------------------------#

_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_source                   'fine-focus sealed tube'
_diffrn_source_type              ?
_diffrn_measurement_device_type  'Bruker X8 APEX-II diffractometer'
_diffrn_measurement_method       '\f-scans and \w-scans'
_diffrn_detector_area_resol_mean 8.333
_diffrn_standards_number         0
_diffrn_reflns_av_R_equivalents  0.0734
_diffrn_reflns_av_unetI/netI     0.0804
_diffrn_reflns_number            15400
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_theta_min         3.68
_diffrn_reflns_theta_max         21.96
_diffrn_reflns_theta_full        21.96
_diffrn_measured_fraction_theta_full 0.995
_diffrn_measured_fraction_theta_max 0.995
_reflns_number_total             2858
_reflns_number_gt                1829
_reflns_threshold_expression     >2sigma(I)

#----------------------------------------------------------------------------#
# COMPUTER PROGRAMS USED #
#----------------------------------------------------------------------------#

_computing_data_collection       'Apex2 (Bruker-Nonius, 2006)'
_computing_cell_refinement       'Saint+ (Bruker-Nonius, 2006)'
_computing_data_reduction        'Saint+ (Bruker-Nonius, 2006)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1997)'
_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^)+(0.0510P)^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    constr
_refine_ls_extinction_method     none
_refine_ls_number_reflns         2858
_refine_ls_number_parameters     316
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0704
_refine_ls_R_factor_gt           0.0333
_refine_ls_wR_factor_ref         0.0683
_refine_ls_wR_factor_gt          0.0627
_refine_ls_goodness_of_fit_ref   0.846
_refine_ls_restrained_S_all      0.846
_refine_ls_shift/su_max          0
_refine_ls_shift/su_mean         0
_refine_diff_density_max         0.17
_refine_diff_density_min         -0.213
_refine_diff_density_rms         0.043

#----------------------------------------------------------------------------#
# 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
O11 O 0.1195(2) 0.52529(16) 0.42065(10) 0.0424(6) Uani 1 1 d . . .
C97 C 0.1679(3) 0.5532(2) 0.47337(15) 0.0298(8) Uani 1 1 d . . .
C99 C 0.1153(4) 0.6502(2) 0.50394(15) 0.0400(9) Uani 1 1 d . . .
H99A H 0.0403 0.684 0.4753 0.06 Uiso 1 1 calc R . .
H99B H 0.2042 0.6952 0.5111 0.06 Uiso 1 1 calc R . .
H99C H 0.0669 0.635 0.5455 0.06 Uiso 1 1 calc R . .
C98 C 0.2829(4) 0.4923(3) 0.51028(15) 0.0491(10) Uani 1 1 d . . .
H98A H 0.3087 0.4308 0.4857 0.074 Uiso 1 1 calc R . .
H98B H 0.2397 0.4727 0.5521 0.074 Uiso 1 1 calc R . .
H98C H 0.3764 0.533 0.5175 0.074 Uiso 1 1 calc R . .
C1 C 0.7934(3) 0.8949(2) 0.62405(13) 0.0272(8) Uani 1 1 d . . .
H1 H 0.7566 0.8337 0.6431 0.033 Uiso 1 1 calc R . .
C2 C 0.8905(3) 0.9562(2) 0.65803(14) 0.0280(8) Uani 1 1 d . . .
H2 H 0.9209 0.9377 0.7008 0.034 Uiso 1 1 calc R . .
C3 C 0.9467(3) 1.0467(2) 0.63099(14) 0.0275(8) Uani 1 1 d . . .
H3 H 1.015 1.0889 0.6554 0.033 Uiso 1 1 calc R . .
C4 C 0.9038(3) 1.0747(2) 0.56954(13) 0.0248(8) Uani 1 1 d . . .
H4 H 0.9432 1.1359 0.5515 0.03 Uiso 1 1 calc R . .
C5 C 0.8013(3) 1.0134(2) 0.53268(13) 0.0193(7) Uani 1 1 d . . .
C6 C 0.7461(3) 0.9212(2) 0.56012(13) 0.0199(7) Uani 1 1 d . . .
C7 C 0.6469(3) 0.8582(2) 0.52315(13) 0.0202(7) Uani 1 1 d . . .
H7 H 0.6081 0.7973 0.5418 0.024 Uiso 1 1 calc R . .
C8 C 0.6054(3) 0.88274(19) 0.46100(13) 0.0173(7) Uani 1 1 d . . .
C9 C 0.6585(3) 0.9753(2) 0.43392(12) 0.0166(7) Uani 1 1 d . . .
C10 C 0.7527(3) 1.0393(2) 0.46920(13) 0.0195(7) Uani 1 1 d . . .
H10 H 0.7856 1.1019 0.4507 0.023 Uiso 1 1 calc R . .
C11 C 0.6165(3) 1.0029(2) 0.36603(13) 0.0195(7) Uani 1 1 d . . .
C12 C 0.5713(3) 0.91663(18) 0.32146(12) 0.0156(7) Uani 1 1 d . . .
H12 H 0.6671 0.8772 0.3119 0.019 Uiso 1 1 calc R . .
C13 C 0.4592(3) 0.84367(19) 0.35531(12) 0.0184(7) Uani 1 1 d . . .
H13A H 0.3562 0.8762 0.3561 0.022 Uiso 1 1 calc R . .
H13B H 0.4498 0.7809 0.3289 0.022 Uiso 1 1 calc R . .
C14 C 0.5030(3) 0.8135(2) 0.42336(13) 0.0196(7) Uani 1 1 d . . .
C15 C 0.5041(3) 0.95433(18) 0.25651(12) 0.0164(7) Uani 1 1 d . . .
H15 H 0.4077 0.9934 0.2658 0.02 Uiso 1 1 calc R . .
C16 C 0.6098(3) 1.02321(19) 0.21862(12) 0.0141(6) Uani 1 1 d . . .
C17 C 0.7568(3) 0.98091(19) 0.19748(12) 0.0144(6) Uani 1 1 d . . .
C18 C 0.7721(3) 0.87579(19) 0.18420(12) 0.0164(7) Uani 1 1 d . . .
C19 C 0.4616(3) 0.86742(19) 0.20956(12) 0.0190(7) Uani 1 1 d . . .
H19A H 0.422 0.8971 0.1685 0.023 Uiso 1 1 calc R . .
H19B H 0.3779 0.8261 0.2285 0.023 Uiso 1 1 calc R . .
C20 C 0.5580(3) 1.11622(19) 0.19899(12) 0.0154(7) Uani 1 1 d . . .
C21 C 0.4116(4) 1.15698(19) 0.21910(13) 0.0196(7) Uani 1 1 d . . .
C22 C 0.6335(3) 1.1816(2) 0.15370(14) 0.0193(7) Uani 1 1 d . . .
C23 C 0.8863(3) 1.0433(2) 0.18909(12) 0.0183(7) Uani 1 1 d . . .
H23 H 0.8787 1.1139 0.1989 0.022 Uiso 1 1 calc R . .
C24 C 1.0248(3) 1.0054(2) 0.16692(12) 0.0206(7) Uani 1 1 d . . .
H24 H 1.1105 1.0495 0.1608 0.025 Uiso 1 1 calc R . .
C25 C 1.0367(3) 0.9027(2) 0.15379(13) 0.0225(7) Uani 1 1 d . . .
H25 H 1.1315 0.876 0.1386 0.027 Uiso 1 1 calc R . .
C26 C 0.9134(3) 0.8383(2) 0.16237(13) 0.0227(7) Uani 1 1 d . . .
H26 H 0.9243 0.7676 0.1534 0.027 Uiso 1 1 calc R . .
N1 N 0.2958(3) 1.19187(17) 0.23308(11) 0.0285(6) Uani 1 1 d . . .
N2 N 0.6857(3) 1.23824(18) 0.11778(12) 0.0294(6) Uani 1 1 d . . .
O1 O 0.6231(2) 1.09124(14) 0.34711(9) 0.0314(5) Uani 1 1 d . . .
O2 O 0.4525(2) 0.73484(14) 0.44670(8) 0.0291(5) Uani 1 1 d . . .
S1 S 0.62329(8) 0.78536(5) 0.19231(3) 0.0215(2) Uani 1 1 d . . .

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
O11 0.0474(15) 0.0533(15) 0.0263(14) -0.0047(12) -0.0102(12) -0.0024(12)
C97 0.027(2) 0.041(2) 0.021(2) 0.0039(17) -0.0013(16) -0.0083(17)
C99 0.044(2) 0.041(2) 0.035(2) 0.0009(17) -0.0028(17) -0.0072(18)
C98 0.044(2) 0.065(2) 0.038(2) -0.0067(19) -0.0082(18) 0.009(2)
C1 0.0301(19) 0.0295(18) 0.0220(18) 0.0029(15) -0.0007(15) 0.0048(17)
C2 0.0258(19) 0.039(2) 0.0195(18) -0.0002(16) -0.0068(15) 0.0070(16)
C3 0.0194(18) 0.040(2) 0.0227(19) -0.0089(16) -0.0049(14) 0.0026(16)
C4 0.0195(18) 0.0305(18) 0.0244(19) -0.0033(15) 0.0022(15) 0.0006(15)
C5 0.0155(17) 0.0219(17) 0.0205(18) -0.0058(14) 0.0006(14) 0.0044(14)
C6 0.0166(17) 0.0266(18) 0.0165(17) -0.0022(14) 0.0022(14) 0.0067(15)
C7 0.0213(18) 0.0199(16) 0.0194(18) 0.0012(14) 0.0033(14) 0.0012(15)
C8 0.0166(16) 0.0194(16) 0.0160(17) -0.0021(14) 0.0031(13) 0.0022(14)
C9 0.0133(16) 0.0206(16) 0.0160(16) -0.0015(14) 0.0039(13) 0.0051(14)
C10 0.0193(17) 0.0189(16) 0.0203(18) -0.0008(14) 0.0043(14) 0.0021(14)
C11 0.0175(17) 0.0211(18) 0.0200(18) 0.0020(14) 0.0020(14) 0.0007(14)
C12 0.0139(16) 0.0183(16) 0.0147(16) 0.0000(13) 0.0009(13) 0.0004(13)
C13 0.0169(17) 0.0191(16) 0.0193(17) 0.0003(13) 0.0010(13) -0.0007(14)
C14 0.0161(17) 0.0220(18) 0.0208(17) 0.0013(14) 0.0041(14) 0.0046(15)
C15 0.0154(16) 0.0148(15) 0.0190(16) 0.0026(13) 0.0000(13) 0.0028(13)
C16 0.0166(17) 0.0148(15) 0.0107(15) -0.0036(12) -0.0091(13) -0.0029(14)
C17 0.0147(16) 0.0153(16) 0.0133(16) 0.0008(12) -0.0043(13) 0.0012(14)
C18 0.0181(17) 0.0192(16) 0.0118(15) 0.0005(13) -0.0046(13) -0.0017(14)
C19 0.0153(16) 0.0200(16) 0.0215(17) 0.0043(13) -0.0012(13) -0.0036(13)
C20 0.0123(16) 0.0185(16) 0.0153(16) -0.0007(13) -0.0018(13) -0.0016(14)
C21 0.031(2) 0.0115(15) 0.0166(17) 0.0061(13) -0.0068(15) -0.0043(16)
C22 0.0185(17) 0.0174(16) 0.0218(18) 0.0000(14) -0.0073(15) 0.0010(14)
C23 0.0240(18) 0.0162(15) 0.0147(16) 0.0002(13) -0.0040(14) -0.0018(15)
C24 0.0140(17) 0.0271(18) 0.0206(17) -0.0018(14) -0.0024(13) -0.0038(15)
C25 0.0157(17) 0.0303(18) 0.0216(18) -0.0038(15) 0.0010(14) 0.0060(16)
C26 0.0244(19) 0.0202(16) 0.0236(17) -0.0008(13) -0.0025(14) 0.0047(15)
N1 0.0313(17) 0.0267(15) 0.0276(16) 0.0047(12) 0.0001(13) 0.0067(13)
N2 0.0277(16) 0.0287(15) 0.0319(16) 0.0084(13) -0.0034(13) -0.0025(13)
O1 0.0529(15) 0.0170(12) 0.0239(12) 0.0025(10) -0.0101(10) -0.0052(11)
O2 0.0365(13) 0.0255(12) 0.0252(12) 0.0082(10) -0.0017(10) -0.0117(11)
S1 0.0252(5) 0.0173(4) 0.0218(4) -0.0007(4) -0.0002(3) -0.0040(4)

#----------------------------------------------------------------------------#
# 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
O11 C97 1.218(3) . ?
C97 C98 1.481(4) . ?
C97 C99 1.494(4) . ?
C99 H99A 0.98 . ?
C99 H99B 0.98 . ?
C99 H99C 0.98 . ?
C98 H98A 0.98 . ?
C98 H98B 0.98 . ?
C98 H98C 0.98 . ?
C1 C2 1.353(4) . ?
C1 C6 1.421(4) . ?
C1 H1 0.95 . ?
C2 C3 1.402(4) . ?
C2 H2 0.95 . ?
C3 C4 1.369(4) . ?
C3 H3 0.95 . ?
C4 C5 1.413(4) . ?
C4 H4 0.95 . ?
C5 C10 1.414(4) . ?
C5 C6 1.421(4) . ?
C6 C7 1.409(4) . ?
C7 C8 1.368(3) . ?
C7 H7 0.95 . ?
C8 C9 1.416(3) . ?
C8 C14 1.482(4) . ?
C9 C10 1.373(4) . ?
C9 C11 1.489(4) . ?
C10 H10 0.95 . ?
C11 O1 1.224(3) . ?
C11 C12 1.507(3) . ?
C12 C15 1.538(3) . ?
C12 C13 1.538(3) . ?
C12 H12 1 . ?
C13 C14 1.504(4) . ?
C13 H13A 0.99 . ?
C13 H13B 0.99 . ?
C14 O2 1.222(3) . ?
C15 C16 1.512(3) . ?
C15 C19 1.538(3) . ?
C15 H15 1 . ?
C16 C20 1.359(3) . ?
C16 C17 1.461(3) . ?
C17 C23 1.402(3) . ?
C17 C18 1.412(3) . ?
C18 C26 1.400(4) . ?
C18 S1 1.761(3) . ?
C19 S1 1.806(3) . ?
C19 H19A 0.99 . ?
C19 H19B 0.99 . ?
C20 C21 1.443(4) . ?
C20 C22 1.433(4) . ?
C21 N1 1.143(3) . ?
C22 N2 1.147(3) . ?
C23 C24 1.382(3) . ?
C23 H23 0.95 . ?
C24 C25 1.377(3) . ?
C24 H24 0.95 . ?
C25 C26 1.375(4) . ?
C25 H25 0.95 . ?
C26 H26 0.95 . ?

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
O11 C97 C98 121.4(3) . . ?
O11 C97 C99 122.0(3) . . ?
C98 C97 C99 116.6(3) . . ?
C97 C99 H99A 109.5 . . ?
C97 C99 H99B 109.5 . . ?
H99A C99 H99B 109.5 . . ?
C97 C99 H99C 109.5 . . ?
H99A C99 H99C 109.5 . . ?
H99B C99 H99C 109.5 . . ?
C97 C98 H98A 109.5 . . ?
C97 C98 H98B 109.5 . . ?
H98A C98 H98B 109.5 . . ?
C97 C98 H98C 109.5 . . ?
H98A C98 H98C 109.5 . . ?
H98B C98 H98C 109.5 . . ?
C2 C1 C6 120.5(3) . . ?
C2 C1 H1 119.7 . . ?
C6 C1 H1 119.7 . . ?
C1 C2 C3 120.9(3) . . ?
C1 C2 H2 119.6 . . ?
C3 C2 H2 119.6 . . ?
C4 C3 C2 120.3(3) . . ?
C4 C3 H3 119.9 . . ?
C2 C3 H3 119.9 . . ?
C3 C4 C5 120.6(3) . . ?
C3 C4 H4 119.7 . . ?
C5 C4 H4 119.7 . . ?
C10 C5 C4 122.7(3) . . ?
C10 C5 C6 118.5(2) . . ?
C4 C5 C6 118.8(3) . . ?
C7 C6 C5 119.2(2) . . ?
C7 C6 C1 121.9(3) . . ?
C5 C6 C1 118.9(3) . . ?
C8 C7 C6 121.5(2) . . ?
C8 C7 H7 119.2 . . ?
C6 C7 H7 119.2 . . ?
C7 C8 C9 119.3(3) . . ?
C7 C8 C14 119.8(2) . . ?
C9 C8 C14 120.9(2) . . ?
C10 C9 C8 120.6(2) . . ?
C10 C9 C11 119.2(2) . . ?
C8 C9 C11 120.2(2) . . ?
C9 C10 C5 120.9(2) . . ?
C9 C10 H10 119.6 . . ?
C5 C10 H10 119.6 . . ?
O1 C11 C9 121.3(2) . . ?
O1 C11 C12 121.9(2) . . ?
C9 C11 C12 116.8(2) . . ?
C11 C12 C15 112.6(2) . . ?
C11 C12 C13 110.5(2) . . ?
C15 C12 C13 111.3(2) . . ?
C11 C12 H12 107.4 . . ?
C15 C12 H12 107.4 . . ?
C13 C12 H12 107.4 . . ?
C14 C13 C12 115.8(2) . . ?
C14 C13 H13A 108.3 . . ?
C12 C13 H13A 108.3 . . ?
C14 C13 H13B 108.3 . . ?
C12 C13 H13B 108.3 . . ?
H13A C13 H13B 107.4 . . ?
O2 C14 C8 121.7(3) . . ?
O2 C14 C13 120.2(2) . . ?
C8 C14 C13 118.1(2) . . ?
C16 C15 C12 114.8(2) . . ?
C16 C15 C19 104.9(2) . . ?
C12 C15 C19 113.4(2) . . ?
C16 C15 H15 107.8 . . ?
C12 C15 H15 107.8 . . ?
C19 C15 H15 107.8 . . ?
C20 C16 C17 122.5(2) . . ?
C20 C16 C15 119.4(2) . . ?
C17 C16 C15 117.7(2) . . ?
C23 C17 C18 117.9(2) . . ?
C23 C17 C16 121.2(2) . . ?
C18 C17 C16 120.9(2) . . ?
C26 C18 C17 119.4(2) . . ?
C26 C18 S1 116.0(2) . . ?
C17 C18 S1 124.6(2) . . ?
C15 C19 S1 112.68(18) . . ?
C15 C19 H19A 109.1 . . ?
S1 C19 H19A 109.1 . . ?
C15 C19 H19B 109.1 . . ?
S1 C19 H19B 109.1 . . ?
H19A C19 H19B 107.8 . . ?
C16 C20 C21 122.3(2) . . ?
C16 C20 C22 125.4(2) . . ?
C21 C20 C22 112.1(2) . . ?
N1 C21 C20 177.4(3) . . ?
N2 C22 C20 175.5(3) . . ?
C24 C23 C17 122.1(2) . . ?
C24 C23 H23 119 . . ?
C17 C23 H23 119 . . ?
C25 C24 C23 118.9(3) . . ?
C25 C24 H24 120.5 . . ?
C23 C24 H24 120.5 . . ?
C26 C25 C24 121.0(3) . . ?
C26 C25 H25 119.5 . . ?
C24 C25 H25 119.5 . . ?
C25 C26 C18 120.7(3) . . ?
C25 C26 H26 119.7 . . ?
C18 C26 H26 119.7 . . ?
C18 S1 C19 100.88(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 -0.1(4) . . . . ?
C1 C2 C3 C4 0.2(4) . . . . ?
C2 C3 C4 C5 0.5(4) . . . . ?
C3 C4 C5 C10 179.6(3) . . . . ?
C3 C4 C5 C6 -1.2(4) . . . . ?
C10 C5 C6 C7 0.9(4) . . . . ?
C4 C5 C6 C7 -178.4(2) . . . . ?
C10 C5 C6 C1 -179.5(2) . . . . ?
C4 C5 C6 C1 1.2(4) . . . . ?
C2 C1 C6 C7 179.1(2) . . . . ?
C2 C1 C6 C5 -0.6(4) . . . . ?
C5 C6 C7 C8 1.4(4) . . . . ?
C1 C6 C7 C8 -178.2(3) . . . . ?
C6 C7 C8 C9 -2.3(4) . . . . ?
C6 C7 C8 C14 178.9(2) . . . . ?
C7 C8 C9 C10 0.9(4) . . . . ?
C14 C8 C9 C10 179.6(2) . . . . ?
C7 C8 C9 C11 179.2(2) . . . . ?
C14 C8 C9 C11 -2.1(4) . . . . ?
C8 C9 C10 C5 1.4(4) . . . . ?
C11 C9 C10 C5 -176.9(2) . . . . ?
C4 C5 C10 C9 177.0(2) . . . . ?
C6 C5 C10 C9 -2.2(4) . . . . ?
C10 C9 C11 O1 -22.0(4) . . . . ?
C8 C9 C11 O1 159.7(2) . . . . ?
C10 C9 C11 C12 155.8(2) . . . . ?
C8 C9 C11 C12 -22.4(3) . . . . ?
O1 C11 C12 C15 -11.9(4) . . . . ?
C9 C11 C12 C15 170.3(2) . . . . ?
O1 C11 C12 C13 -137.0(3) . . . . ?
C9 C11 C12 C13 45.2(3) . . . . ?
C11 C12 C13 C14 -45.9(3) . . . . ?
C15 C12 C13 C14 -171.8(2) . . . . ?
C7 C8 C14 O2 0.9(4) . . . . ?
C9 C8 C14 O2 -177.8(2) . . . . ?
C7 C8 C14 C13 179.6(2) . . . . ?
C9 C8 C14 C13 0.9(4) . . . . ?
C12 C13 C14 O2 -157.2(2) . . . . ?
C12 C13 C14 C8 24.1(3) . . . . ?
C11 C12 C15 C16 57.7(3) . . . . ?
C13 C12 C15 C16 -177.6(2) . . . . ?
C11 C12 C15 C19 178.3(2) . . . . ?
C13 C12 C15 C19 -57.0(3) . . . . ?
C12 C15 C16 C20 -125.8(2) . . . . ?
C19 C15 C16 C20 109.0(3) . . . . ?
C12 C15 C16 C17 62.0(3) . . . . ?
C19 C15 C16 C17 -63.1(3) . . . . ?
C20 C16 C17 C23 36.9(4) . . . . ?
C15 C16 C17 C23 -151.2(2) . . . . ?
C20 C16 C17 C18 -142.4(3) . . . . ?
C15 C16 C17 C18 29.5(3) . . . . ?
C23 C17 C18 C26 -1.1(4) . . . . ?
C16 C17 C18 C26 178.3(2) . . . . ?
C23 C17 C18 S1 179.60(19) . . . . ?
C16 C17 C18 S1 -1.1(3) . . . . ?
C16 C15 C19 S1 68.8(2) . . . . ?
C12 C15 C19 S1 -57.2(3) . . . . ?
C17 C16 C20 C21 178.9(2) . . . . ?
C15 C16 C20 C21 7.1(4) . . . . ?
C17 C16 C20 C22 3.3(4) . . . . ?
C15 C16 C20 C22 -168.4(2) . . . . ?
C18 C17 C23 C24 1.7(4) . . . . ?
C16 C17 C23 C24 -177.7(2) . . . . ?
C17 C23 C24 C25 -1.2(4) . . . . ?
C23 C24 C25 C26 0.1(4) . . . . ?
C24 C25 C26 C18 0.6(4) . . . . ?
C17 C18 C26 C25 0.0(4) . . . . ?
S1 C18 C26 C25 179.4(2) . . . . ?
C26 C18 S1 C19 -172.3(2) . . . . ?
C17 C18 S1 C19 7.1(2) . . . . ?
C15 C19 S1 C18 -41.3(2) . . . . ?