# Electronic Supplementary Material (ESI) for Organic Chemistry Frontiers.
# This journal is © the Partner Organisations 2016

####################################################################### 
# 
# 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_76
_database_code_depnum_ccdc_archive 'CCDC 1483915'
_audit_update_record             
;
2016-09-12 deposited with the CCDC.
2016-09-22 downloaded from the CCDC.
;

_database_code_CSD               'CCDC 1483915'

#RX1263


_audit_creation_method           SHELXL-2014/7
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_formula_moiety         'C50 H50 N2 O6 S2'
_chemical_formula_sum            'C50 H50 N2 O6 S2'
_chemical_melting_point          ?

_exptl_crystal_description       bloc
_exptl_crystal_colour            colorless
_diffrn_ambient_temperature      100(1)
_chemical_formula_weight         839.04

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0031 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 0.0109 0.0061 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.1250 0.1239 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 21/c'
_space_group_name_Hall           '-P 2ybc'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;

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

_cell_length_a                   12.0255(7)
_cell_length_b                   18.0910(12)
_cell_length_c                   10.1121(7)
_cell_angle_alpha                90
_cell_angle_beta                 105.935(2)
_cell_angle_gamma                90
_cell_volume                     2115.4(2)
_cell_formula_units_Z            2
_cell_measurement_temperature    100(1)
_cell_measurement_reflns_used    5270
_cell_measurement_theta_min      2.38
_cell_measurement_theta_max      30.29
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.317
_exptl_crystal_F_000             888
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.210
_exptl_crystal_size_mid          0.170
_exptl_crystal_size_min          0.090
_exptl_absorpt_coefficient_mu    0.180
_shelx_estimated_absorpt_T_min   0.970
_shelx_estimated_absorpt_T_max   0.987
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.9452
_exptl_absorpt_correction_T_max  0.9912
_exptl_absorpt_process_details   SADABS
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            25809
_diffrn_reflns_av_unetI/netI     0.0529
_diffrn_reflns_av_R_equivalents  0.0506
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_k_min       -25
_diffrn_reflns_limit_k_max       25
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_theta_min         1.761
_diffrn_reflns_theta_max         30.561
_diffrn_reflns_theta_full        25.000
_diffrn_measured_fraction_theta_max 0.933
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.933
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.933
_diffrn_reflns_point_group_measured_fraction_full 0.999
_reflns_number_total             6061
_reflns_number_gt                4268
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;

_computing_data_collection       'Bruker SMART'
_computing_cell_refinement       'Bruker SMART'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    ?
_computing_publication_material  ?
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0488P)²+1.2783P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         6061
_refine_ls_number_parameters     273
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0786
_refine_ls_R_factor_gt           0.0468
_refine_ls_wR_factor_ref         0.1223
_refine_ls_wR_factor_gt          0.1069
_refine_ls_goodness_of_fit_ref   1.023
_refine_ls_restrained_S_all      1.023
_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_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
S1 S 0.31605(3) 0.42971(2) 0.16028(4) 0.01874(11) Uani 1 1 d . . . . .
O1 O 0.32946(10) 0.38374(7) 0.27881(13) 0.0259(3) Uani 1 1 d . . . . .
O2 O 0.36459(10) 0.40714(7) 0.05217(13) 0.0252(3) Uani 1 1 d . . . . .
C1 C 0.37319(12) 0.51687(9) 0.22054(17) 0.0175(3) Uani 1 1 d . . . . .
C5 C 0.43522(16) 0.63810(11) 0.17640(19) 0.0263(4) Uani 1 1 d . . . . .
H5 H 0.4489 0.6728 0.1148 0.032 Uiso 1 1 calc R U . . .
C2 C 0.39396(13) 0.53428(10) 0.35886(17) 0.0215(4) Uani 1 1 d . . . . .
H2 H 0.3792 0.4998 0.4202 0.026 Uiso 1 1 calc R U . . .
C6 C 0.39350(15) 0.56864(10) 0.12882(18) 0.0234(4) Uani 1 1 d . . . . .
H6 H 0.3793 0.5570 0.0361 0.028 Uiso 1 1 calc R U . . .
C4 C 0.45688(14) 0.65669(10) 0.31496(19) 0.0230(4) Uani 1 1 d . . . . .
C3 C 0.43693(14) 0.60366(11) 0.40475(18) 0.0247(4) Uani 1 1 d . . . . .
H3 H 0.4527 0.6148 0.4978 0.030 Uiso 1 1 calc R U . . .
N1 N 0.17745(10) 0.44061(8) 0.09128(14) 0.0162(3) Uani 1 1 d . . . . .
C17 C 0.10350(13) 0.29858(9) -0.16361(17) 0.0175(3) Uani 1 1 d . . . . .
C12 C 0.02779(13) 0.33977(9) -0.10877(16) 0.0153(3) Uani 1 1 d . . . . .
C13 C -0.04497(13) 0.30183(9) -0.04656(16) 0.0178(3) Uani 1 1 d . . . . .
H13 H -0.0955 0.3287 -0.0101 0.021 Uiso 1 1 calc R U . . .
C7 C 0.10514(13) 0.46328(9) 0.18102(16) 0.0173(3) Uani 1 1 d . . . . .
H7A H 0.1447 0.4506 0.2755 0.021 Uiso 1 1 calc R U . . .
H7B H 0.0329 0.4360 0.1551 0.021 Uiso 1 1 calc R U . . .
C11 C 0.02234(13) 0.42212(9) -0.11710(16) 0.0154(3) Uani 1 1 d . . . . .
C14 C -0.04485(14) 0.22489(10) -0.03692(17) 0.0194(3) Uani 1 1 d . . . . .
C9 C 0.13476(13) 0.46237(9) -0.05440(16) 0.0165(3) Uani 1 1 d . . . . .
H9A H 0.1913 0.4495 -0.1030 0.020 Uiso 1 1 calc R U . . .
H9B H 0.1223 0.5154 -0.0615 0.020 Uiso 1 1 calc R U . . .
C21 C -0.15084(15) 0.05012(10) -0.03173(18) 0.0226(4) Uani 1 1 d . . . . .
H21 H -0.0840 0.0394 0.0376 0.027 Uiso 1 1 calc R U . . .
C8 C 0.07948(13) 0.54452(9) 0.17211(16) 0.0169(3) Uani 1 1 d . . . . .
H8 H 0.1418 0.5756 0.2093 0.020 Uiso 1 1 calc R U . . .
C16 C 0.10540(15) 0.22204(10) -0.15405(18) 0.0217(4) Uani 1 1 d . . . . .
H16 H 0.1564 0.1949 -0.1893 0.026 Uiso 1 1 calc R U . . .
C25 C -0.28912(15) 0.13744(11) -0.15812(18) 0.0253(4) Uani 1 1 d . . . . .
H25 H -0.3153 0.1858 -0.1748 0.030 Uiso 1 1 calc R U . . .
C24 C -0.34964(15) 0.08059(12) -0.23888(19) 0.0284(4) Uani 1 1 d . . . . .
H24 H -0.4164 0.0911 -0.3084 0.034 Uiso 1 1 calc R U . . .
C18 C 0.25372(15) 0.29813(11) -0.2752(2) 0.0267(4) Uani 1 1 d . . . . .
H18A H 0.3046 0.2733 -0.1980 0.040 Uiso 1 1 calc R U . . .
H18B H 0.2975 0.3319 -0.3144 0.040 Uiso 1 1 calc R U . . .
H18C H 0.2166 0.2623 -0.3431 0.040 Uiso 1 1 calc R U . . .
C15 C 0.03139(15) 0.18620(10) -0.09195(18) 0.0219(4) Uani 1 1 d . . . . .
H15 H 0.0328 0.1349 -0.0870 0.026 Uiso 1 1 calc R U . . .
C23 C -0.31144(15) 0.00913(11) -0.21664(19) 0.0273(4) Uani 1 1 d . . . . .
H23 H -0.3526 -0.0289 -0.2703 0.033 Uiso 1 1 calc R U . . .
C20 C -0.18987(14) 0.12284(10) -0.05255(17) 0.0212(4) Uani 1 1 d . . . . .
C22 C -0.21088(17) -0.00633(11) -0.1136(2) 0.0279(4) Uani 1 1 d . . . . .
H22 H -0.1839 -0.0547 -0.0995 0.034 Uiso 1 1 calc R U . . .
C19 C -0.12429(15) 0.18519(10) 0.03316(18) 0.0239(4) Uani 1 1 d . . . . .
H19A H -0.0787 0.1657 0.1206 0.029 Uiso 1 1 calc R U . . .
H19B H -0.1790 0.2204 0.0517 0.029 Uiso 1 1 calc R U . . .
C10 C 0.50118(16) 0.73196(11) 0.3683(2) 0.0318(4) Uani 1 1 d . . . . .
H10A H 0.4404 0.7593 0.3907 0.048 Uiso 1 1 calc R U . . .
H10B H 0.5264 0.7580 0.2990 0.048 Uiso 1 1 calc R U . . .
H10C H 0.5649 0.7265 0.4491 0.048 Uiso 1 1 calc R U . . .
O3 O 0.16810(10) 0.33812(7) -0.23061(12) 0.0209(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
S1 O1 1.4311(13) . ?
S1 O2 1.4329(13) . ?
S1 N1 1.6326(13) . ?
S1 C1 1.7607(17) . ?
C1 C6 1.386(2) . ?
C1 C2 1.388(2) . ?
C5 C6 1.389(3) . ?
C5 C4 1.394(3) . ?
C2 C3 1.388(3) . ?
C4 C3 1.386(3) . ?
C4 C10 1.507(3) . ?
N1 C9 1.474(2) . ?
N1 C7 1.477(2) . ?
C17 O3 1.365(2) . ?
C17 C16 1.388(2) . ?
C17 C12 1.403(2) . ?
C12 C13 1.391(2) . ?
C12 C11 1.493(2) . ?
C13 C14 1.395(2) . ?
C7 C8 1.499(2) . ?
C11 C8 1.341(2) 3_565 ?
C11 C9 1.513(2) . ?
C14 C15 1.386(2) . ?
C14 C19 1.517(2) . ?
C21 C22 1.386(3) . ?
C21 C20 1.393(3) . ?
C8 C11 1.341(2) 3_565 ?
C16 C15 1.383(2) . ?
C25 C24 1.389(3) . ?
C25 C20 1.391(2) . ?
C24 C23 1.370(3) . ?
C18 O3 1.429(2) . ?
C23 C22 1.391(3) . ?
C20 C19 1.507(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
O1 S1 O2 119.84(8) . . ?
O1 S1 N1 107.17(7) . . ?
O2 S1 N1 106.87(7) . . ?
O1 S1 C1 106.69(8) . . ?
O2 S1 C1 108.50(8) . . ?
N1 S1 C1 107.18(7) . . ?
C6 C1 C2 120.33(16) . . ?
C6 C1 S1 119.82(13) . . ?
C2 C1 S1 119.81(13) . . ?
C6 C5 C4 121.09(17) . . ?
C1 C2 C3 119.32(16) . . ?
C1 C6 C5 119.51(16) . . ?
C3 C4 C5 118.24(17) . . ?
C3 C4 C10 119.90(17) . . ?
C5 C4 C10 121.86(17) . . ?
C4 C3 C2 121.49(16) . . ?
C9 N1 C7 115.95(12) . . ?
C9 N1 S1 119.59(10) . . ?
C7 N1 S1 118.37(10) . . ?
O3 C17 C16 123.83(15) . . ?
O3 C17 C12 115.93(15) . . ?
C16 C17 C12 120.15(15) . . ?
C13 C12 C17 118.27(15) . . ?
C13 C12 C11 119.65(14) . . ?
C17 C12 C11 122.07(14) . . ?
C12 C13 C14 122.36(15) . . ?
N1 C7 C8 112.42(13) . . ?
C8 C11 C12 119.56(14) 3_565 . ?
C8 C11 C9 124.50(15) 3_565 . ?
C12 C11 C9 115.87(13) . . ?
C15 C14 C13 117.65(15) . . ?
C15 C14 C19 121.28(16) . . ?
C13 C14 C19 121.07(15) . . ?
N1 C9 C11 108.43(13) . . ?
C22 C21 C20 120.46(17) . . ?
C11 C8 C7 127.97(15) 3_565 . ?
C15 C16 C17 119.94(16) . . ?
C24 C25 C20 120.77(18) . . ?
C23 C24 C25 120.30(17) . . ?
C16 C15 C14 121.63(17) . . ?
C24 C23 C22 119.75(17) . . ?
C25 C20 C21 118.54(16) . . ?
C25 C20 C19 120.17(17) . . ?
C21 C20 C19 121.24(16) . . ?
C21 C22 C23 120.16(18) . . ?
C20 C19 C14 112.52(14) . . ?
C17 O3 C18 116.67(13) . . ?

_refine_diff_density_max         0.465
_refine_diff_density_min         -0.417
_refine_diff_density_rms         0.064


_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_h-m   'P 21/c'
_symmetry_int_tables_number      14
_chemical_absolute_configuration .

####################################################################### 
# 
# 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_66
_database_code_depnum_ccdc_archive 'CCDC 1483916'
_audit_update_record             
;
2016-09-12 deposited with the CCDC.
2016-09-22 downloaded from the CCDC.
;

_database_code_CSD               'CCDC 1483916'



#v101GuillotICMMO



_audit_creation_method           SHELXL-2014/7
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_formula_moiety         'C18 H22 O4'
_chemical_formula_sum            'C18 H22 O4'
_chemical_melting_point          ?

_exptl_crystal_description       plate
_exptl_crystal_colour            colorless
_diffrn_ambient_temperature      100(1)
_chemical_formula_weight         302.35

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      orthorhombic
_space_group_IT_number           61
_space_group_name_H-M_alt        'P b c a'
_space_group_name_Hall           '-P 2ac 2ab'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;

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

_cell_length_a                   7.6825(3)
_cell_length_b                   17.5861(8)
_cell_length_c                   22.9639(11)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     3102.5(2)
_cell_formula_units_Z            8
_cell_measurement_temperature    100(1)
_cell_measurement_reflns_used    9068
_cell_measurement_theta_min      2.48
_cell_measurement_theta_max      33.48
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.295
_exptl_crystal_F_000             1296
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.110
_exptl_crystal_size_mid          0.100
_exptl_crystal_size_min          0.030
_exptl_absorpt_coefficient_mu    0.090
_shelx_estimated_absorpt_T_min   0.990
_shelx_estimated_absorpt_T_max   0.997
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.9711
_exptl_absorpt_correction_T_max  0.9941
_exptl_absorpt_process_details   SADABS
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker PHOTON100 CMOS'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            33166
_diffrn_reflns_av_unetI/netI     0.0362
_diffrn_reflns_av_R_equivalents  0.0423
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -24
_diffrn_reflns_limit_k_max       27
_diffrn_reflns_limit_l_min       -33
_diffrn_reflns_limit_l_max       28
_diffrn_reflns_theta_min         2.918
_diffrn_reflns_theta_max         33.765
_diffrn_reflns_theta_full        25.000
_diffrn_measured_fraction_theta_max 0.912
_diffrn_measured_fraction_theta_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.912
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.912
_diffrn_reflns_point_group_measured_fraction_full 0.997
_reflns_number_total             5651
_reflns_number_gt                4920
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;

_computing_data_collection       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick 2008)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    ?
_computing_publication_material  ?
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0724P)²+2.7652P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         5651
_refine_ls_number_parameters     205
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0669
_refine_ls_R_factor_gt           0.0581
_refine_ls_wR_factor_ref         0.1604
_refine_ls_wR_factor_gt          0.1538
_refine_ls_goodness_of_fit_ref   1.041
_refine_ls_restrained_S_all      1.041
_refine_ls_shift/su_max          0.001
_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_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
O2 O 0.22726(12) 0.86007(5) 0.50652(4) 0.01541(18) Uani 1 1 d . . . . .
O4 O 0.44360(12) 0.87109(5) 0.39296(4) 0.01665(18) Uani 1 1 d . . . . .
O1 O -0.00892(13) 0.89912(6) 0.45723(5) 0.0221(2) Uani 1 1 d . . . . .
O3 O 0.46972(14) 0.75239(6) 0.42813(5) 0.0243(2) Uani 1 1 d . . . . .
C17 C 0.38082(15) 0.80467(6) 0.41253(5) 0.0126(2) Uani 1 1 d . . . . .
C15 C 0.12061(15) 0.86086(7) 0.46048(5) 0.0134(2) Uani 1 1 d . . . . .
C5 C 0.12904(15) 0.70255(7) 0.31651(5) 0.0139(2) Uani 1 1 d . . . . .
C13 C 0.18085(15) 0.80644(6) 0.41250(5) 0.0128(2) Uani 1 1 d . . . . .
C12 C 0.10898(16) 0.83270(7) 0.35445(5) 0.0145(2) Uani 1 1 d . . . . .
H12 H 0.0814 0.8838 0.3495 0.017 Uiso 1 1 calc R U . . .
C16 C 0.17197(18) 0.90657(7) 0.55547(5) 0.0178(2) Uani 1 1 d . . . . .
H16A H 0.1532 0.9578 0.5426 0.027 Uiso 1 1 calc R U . . .
H16B H 0.2605 0.9060 0.5850 0.027 Uiso 1 1 calc R U . . .
H16C H 0.0657 0.8865 0.5712 0.027 Uiso 1 1 calc R U . . .
C6 C 0.13338(15) 0.67379(7) 0.37404(5) 0.0134(2) Uani 1 1 d . . . . .
C7 C 0.15405(18) 0.56336(7) 0.44517(5) 0.0178(2) Uani 1 1 d . . . . .
H7A H 0.2562 0.5793 0.4659 0.027 Uiso 1 1 calc R U . . .
H7B H 0.1518 0.5089 0.4430 0.027 Uiso 1 1 calc R U . . .
H7C H 0.0522 0.5810 0.4653 0.027 Uiso 1 1 calc R U . . .
C2 C 0.18456(17) 0.54816(7) 0.33698(6) 0.0177(2) Uani 1 1 d . . . . .
H2 H 0.2001 0.4964 0.3435 0.021 Uiso 1 1 calc R U . . .
C10 C 0.08380(16) 0.78449(7) 0.30990(5) 0.0146(2) Uani 1 1 d . . . . .
C1 C 0.15719(16) 0.59608(7) 0.38465(5) 0.0147(2) Uani 1 1 d . . . . .
C11 C -0.00068(19) 0.81622(8) 0.25529(6) 0.0202(2) Uani 1 1 d . . . . .
H11A H -0.0748 0.8581 0.2655 0.030 Uiso 1 1 calc R U . . .
H11B H -0.0686 0.7772 0.2369 0.030 Uiso 1 1 calc R U . . .
H11C H 0.0880 0.8334 0.2289 0.030 Uiso 1 1 calc R U . . .
C3 C 0.18932(17) 0.57510(7) 0.28012(6) 0.0179(2) Uani 1 1 d . . . . .
C14 C 0.10661(17) 0.72736(7) 0.42513(5) 0.0153(2) Uani 1 1 d . . . . .
H14A H 0.1630 0.7065 0.4594 0.018 Uiso 1 1 calc R U . . .
H14B H -0.0168 0.7316 0.4334 0.018 Uiso 1 1 calc R U . . .
C4 C 0.16179(16) 0.65293(7) 0.26887(5) 0.0160(2) Uani 1 1 d . . . . .
C18 C 0.63106(18) 0.87883(9) 0.39525(6) 0.0241(3) Uani 1 1 d . . . . .
H18A H 0.6690 0.8768 0.4350 0.036 Uiso 1 1 calc R U . . .
H18B H 0.6644 0.9267 0.3785 0.036 Uiso 1 1 calc R U . . .
H18C H 0.6841 0.8381 0.3737 0.036 Uiso 1 1 calc R U . . .
C9 C 0.1723(2) 0.67834(8) 0.20609(6) 0.0223(3) Uani 1 1 d . . . . .
H9A H 0.2592 0.6490 0.1861 0.033 Uiso 1 1 calc R U . . .
H9B H 0.2030 0.7312 0.2046 0.033 Uiso 1 1 calc R U . . .
H9C H 0.0614 0.6710 0.1877 0.033 Uiso 1 1 calc R U . . .
C8 C 0.2218(2) 0.51944(8) 0.23116(7) 0.0266(3) Uani 1 1 d . . . . .
H8A H 0.2308 0.4689 0.2468 0.040 Uiso 1 1 calc R U . . .
H8B H 0.3283 0.5324 0.2117 0.040 Uiso 1 1 calc R U . . .
H8C H 0.1271 0.5216 0.2040 0.040 Uiso 1 1 calc R U . . .


_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 C15 1.3377(15) . ?
O2 C16 1.4535(15) . ?
O4 C17 1.3412(14) . ?
O4 C18 1.4475(16) . ?
O1 C15 1.2035(15) . ?
O3 C17 1.2000(15) . ?
C17 C13 1.5366(17) . ?
C15 C13 1.5309(16) . ?
C5 C6 1.4150(16) . ?
C5 C4 1.4218(17) . ?
C5 C10 1.4901(17) . ?
C13 C12 1.5150(17) . ?
C13 C14 1.5308(16) . ?
C12 C10 1.3427(17) . ?
C12 H12 0.9300 . ?
C16 H16A 0.9600 . ?
C16 H16B 0.9600 . ?
C16 H16C 0.9600 . ?
C6 C1 1.4000(16) . ?
C6 C14 1.5188(17) . ?
C7 C1 1.5044(17) . ?
C7 H7A 0.9600 . ?
C7 H7B 0.9600 . ?
C7 H7C 0.9600 . ?
C2 C3 1.3896(19) . ?
C2 C1 1.3974(17) . ?
C2 H2 0.9300 . ?
C10 C11 1.5185(17) . ?
C11 H11A 0.9600 . ?
C11 H11B 0.9600 . ?
C11 H11C 0.9600 . ?
C3 C4 1.4088(18) . ?
C3 C8 1.5116(18) . ?
C14 H14A 0.9700 . ?
C14 H14B 0.9700 . ?
C4 C9 1.5115(18) . ?
C18 H18A 0.9600 . ?
C18 H18B 0.9600 . ?
C18 H18C 0.9600 . ?
C9 H9A 0.9600 . ?
C9 H9B 0.9600 . ?
C9 H9C 0.9600 . ?
C8 H8A 0.9600 . ?
C8 H8B 0.9600 . ?
C8 H8C 0.9600 . ?

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
C15 O2 C16 115.24(10) . . ?
C17 O4 C18 115.31(11) . . ?
O3 C17 O4 124.23(12) . . ?
O3 C17 C13 125.78(11) . . ?
O4 C17 C13 109.98(10) . . ?
O1 C15 O2 124.13(11) . . ?
O1 C15 C13 123.70(11) . . ?
O2 C15 C13 112.16(10) . . ?
C6 C5 C4 119.65(11) . . ?
C6 C5 C10 116.50(10) . . ?
C4 C5 C10 123.81(11) . . ?
C12 C13 C15 109.42(10) . . ?
C12 C13 C14 107.93(9) . . ?
C15 C13 C14 108.60(9) . . ?
C12 C13 C17 111.77(10) . . ?
C15 C13 C17 108.34(9) . . ?
C14 C13 C17 110.73(10) . . ?
C10 C12 C13 122.03(11) . . ?
C10 C12 H12 119.0 . . ?
C13 C12 H12 119.0 . . ?
O2 C16 H16A 109.5 . . ?
O2 C16 H16B 109.5 . . ?
H16A C16 H16B 109.5 . . ?
O2 C16 H16C 109.5 . . ?
H16A C16 H16C 109.5 . . ?
H16B C16 H16C 109.5 . . ?
C1 C6 C5 120.96(11) . . ?
C1 C6 C14 119.26(11) . . ?
C5 C6 C14 119.76(10) . . ?
C1 C7 H7A 109.5 . . ?
C1 C7 H7B 109.5 . . ?
H7A C7 H7B 109.5 . . ?
C1 C7 H7C 109.5 . . ?
H7A C7 H7C 109.5 . . ?
H7B C7 H7C 109.5 . . ?
C3 C2 C1 122.31(11) . . ?
C3 C2 H2 118.8 . . ?
C1 C2 H2 118.8 . . ?
C12 C10 C5 119.97(11) . . ?
C12 C10 C11 117.31(11) . . ?
C5 C10 C11 122.63(11) . . ?
C2 C1 C6 118.16(11) . . ?
C2 C1 C7 119.70(11) . . ?
C6 C1 C7 122.14(11) . . ?
C10 C11 H11A 109.5 . . ?
C10 C11 H11B 109.5 . . ?
H11A C11 H11B 109.5 . . ?
C10 C11 H11C 109.5 . . ?
H11A C11 H11C 109.5 . . ?
H11B C11 H11C 109.5 . . ?
C2 C3 C4 119.97(11) . . ?
C2 C3 C8 118.85(12) . . ?
C4 C3 C8 121.18(12) . . ?
C6 C14 C13 111.51(10) . . ?
C6 C14 H14A 109.3 . . ?
C13 C14 H14A 109.3 . . ?
C6 C14 H14B 109.3 . . ?
C13 C14 H14B 109.3 . . ?
H14A C14 H14B 108.0 . . ?
C3 C4 C5 118.80(11) . . ?
C3 C4 C9 117.01(11) . . ?
C5 C4 C9 124.18(12) . . ?
O4 C18 H18A 109.5 . . ?
O4 C18 H18B 109.5 . . ?
H18A C18 H18B 109.5 . . ?
O4 C18 H18C 109.5 . . ?
H18A C18 H18C 109.5 . . ?
H18B C18 H18C 109.5 . . ?
C4 C9 H9A 109.5 . . ?
C4 C9 H9B 109.5 . . ?
H9A C9 H9B 109.5 . . ?
C4 C9 H9C 109.5 . . ?
H9A C9 H9C 109.5 . . ?
H9B C9 H9C 109.5 . . ?
C3 C8 H8A 109.5 . . ?
C3 C8 H8B 109.5 . . ?
H8A C8 H8B 109.5 . . ?
C3 C8 H8C 109.5 . . ?
H8A C8 H8C 109.5 . . ?
H8B C8 H8C 109.5 . . ?

_refine_diff_density_max         0.735
_refine_diff_density_min         -0.324
_refine_diff_density_rms         0.067


_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_h-m   'P b c a'
_symmetry_int_tables_number      61
_chemical_absolute_configuration .

