# Electronic Supplementary Material (ESI) for Chemical Science.
# This journal is © The Royal Society of Chemistry 2018

####################################################################### 
# 
# 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_a
_audit_block_doi                 10.5517/ccdc.csd.cc1q0d59
_database_code_depnum_ccdc_archive 'CCDC 1579300'
_audit_update_record             
;
2017-10-11 deposited with the CCDC.
2018-04-11 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C19 H21 O2 S'
_chemical_formula_sum            'C19 H21 O2 S'
_chemical_formula_weight         313.42

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 '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 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.3331 0.5567 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      monoclinic
_space_group_IT_number           4
_space_group_name_H-M_alt        'P 21'
_space_group_name_Hall           'P 2yb'

_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'

_cell_length_a                   6.6120(6)
_cell_length_b                   7.8997(7)
_cell_length_c                   15.4119(13)
_cell_angle_alpha                90
_cell_angle_beta                 92.455(3)
_cell_angle_gamma                90
_cell_volume                     804.27(12)
_cell_formula_units_Z            2
_cell_measurement_temperature    173(2)
_cell_measurement_reflns_used    9254
_cell_measurement_theta_min      2.87
_cell_measurement_theta_max      66.67

_exptl_crystal_description       block
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.294
_exptl_crystal_F_000             608
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.05
_exptl_crystal_size_mid          0.04
_exptl_crystal_size_min          0.03
_exptl_absorpt_coefficient_mu    1.815
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   none
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      173(2)
_diffrn_radiation_wavelength     1.54178
_diffrn_radiation_type           CuK\a
_diffrn_source                   'sealed tube'
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            10232
_diffrn_reflns_av_unetI/netI     0.0355
_diffrn_reflns_av_R_equivalents  0.0340
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_theta_min         2.870
_diffrn_reflns_theta_max         66.577
_diffrn_reflns_theta_full        66.577
_diffrn_measured_fraction_theta_max 0.992
_diffrn_measured_fraction_theta_full 0.992
_diffrn_reflns_Laue_measured_fraction_max 0.992
_diffrn_reflns_Laue_measured_fraction_full 0.992
_diffrn_reflns_point_group_measured_fraction_max 0.978
_diffrn_reflns_point_group_measured_fraction_full 0.978
_reflns_number_total             2796
_reflns_number_gt                2737
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.827
_reflns_Friedel_fraction_max     0.961
_reflns_Friedel_fraction_full    0.961

_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 (Sheldrick, 2014)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_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)+(0.1354P)²+1.7916P] 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_abs_structure_details 
;
 Flack x determined using 1201 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.123(9)
_chemical_absolute_configuration ad
_refine_ls_number_reflns         2796
_refine_ls_number_parameters     203
_refine_ls_number_restraints     193
_refine_ls_R_factor_all          0.0840
_refine_ls_R_factor_gt           0.0824
_refine_ls_wR_factor_ref         0.2279
_refine_ls_wR_factor_gt          0.2256
_refine_ls_goodness_of_fit_ref   1.044
_refine_ls_restrained_S_all      1.057
_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 0.0255(3) 0.2085(3) 0.72576(12) 0.0501(6) Uani 1 1 d . U . . .
O1 O 0.3499(7) 0.5300(6) 0.9675(3) 0.0330(11) Uani 1 1 d . U . . .
H1 H 0.4558 0.4723 0.9754 0.049 Uiso 1 1 calc R U . . .
C1 C 0.3269(10) 0.3234(8) 0.8490(4) 0.0271(13) Uani 1 1 d . U . . .
O2 O 0.6426(7) 0.3204(6) 0.9443(3) 0.0338(11) Uani 1 1 d . U . . .
H2 H 0.6706 0.2268 0.9677 0.051 Uiso 1 1 calc R U . . .
C2 C 0.2683(9) 0.2922(8) 0.7534(4) 0.0247(13) Uani 1 1 d . U . . .
C3 C 0.4302(10) 0.3259(9) 0.6766(4) 0.0295(13) Uani 1 1 d . U . . .
H3A H 0.4597 0.4474 0.6678 0.035 Uiso 1 1 calc R U . . .
H3B H 0.5576 0.2610 0.6854 0.035 Uiso 1 1 calc R U . . .
C5 C 0.0888(11) 0.1930(9) 0.6185(4) 0.0344(14) Uani 1 1 d . U . . .
C4 C 0.2813(12) 0.2479(8) 0.6019(4) 0.0343(15) Uani 1 1 d . U . . .
C6 C -0.0396(14) 0.1237(11) 0.5523(6) 0.0461(19) Uani 1 1 d . U . . .
H6 H -0.1729 0.0875 0.5638 0.055 Uiso 1 1 calc R U . . .
C7 C 0.0341(15) 0.1103(11) 0.4708(5) 0.050(2) Uani 1 1 d . U . . .
H7 H -0.0494 0.0616 0.4257 0.061 Uiso 1 1 calc R U . . .
C9 C 0.3500(12) 0.2350(10) 0.5156(5) 0.0424(17) Uani 1 1 d . U . . .
H9 H 0.4806 0.2743 0.5020 0.051 Uiso 1 1 calc R U . . .
C8 C 0.2224(15) 0.1642(11) 0.4524(5) 0.051(2) Uani 1 1 d . U . . .
H8 H 0.2672 0.1529 0.3949 0.061 Uiso 1 1 calc R U . . .
C10 C 0.2234(10) 0.1936(10) 0.9050(4) 0.0351(15) Uani 1 1 d . U . . .
H10A H 0.2710 0.0799 0.8906 0.053 Uiso 1 1 calc R U . . .
H10B H 0.0765 0.1999 0.8939 0.053 Uiso 1 1 calc R U . . .
H10C H 0.2560 0.2173 0.9664 0.053 Uiso 1 1 calc R U . . .
C11 C 0.5584(10) 0.2927(9) 0.8579(4) 0.0290(14) Uani 1 1 d . U . . .
H11A H 0.5870 0.1748 0.8405 0.035 Uiso 1 1 calc R U . . .
H11B H 0.6265 0.3689 0.8174 0.035 Uiso 1 1 calc R U . . .
C12 C 0.2726(9) 0.5091(9) 0.8782(4) 0.0276(13) Uani 1 1 d . U . . .
C13 C 0.0473(10) 0.5386(11) 0.8836(5) 0.0384(17) Uani 1 1 d . U . . .
H13A H -0.0063 0.4648 0.9283 0.058 Uiso 1 1 calc R U . . .
H13B H -0.0205 0.5129 0.8273 0.058 Uiso 1 1 calc R U . . .
H13C H 0.0227 0.6571 0.8987 0.058 Uiso 1 1 calc R U . . .
C14 C 0.3661(10) 0.6423(8) 0.8204(4) 0.0280(13) Uani 1 1 d . U . . .
C15 C 0.5581(10) 0.7079(10) 0.8413(4) 0.0317(13) Uani 1 1 d . U . . .
H15 H 0.6308 0.6691 0.8920 0.038 Uiso 1 1 calc R U . . .
C16 C 0.6447(12) 0.8296(9) 0.7889(5) 0.0401(17) Uani 1 1 d . U . . .
H16 H 0.7757 0.8728 0.8038 0.048 Uiso 1 1 calc R U . . .
C17 C 0.5399(14) 0.8870(10) 0.7155(5) 0.0468(19) Uani 1 1 d . U . . .
H17 H 0.5984 0.9707 0.6801 0.056 Uiso 1 1 calc R U . . .
C18 C 0.3504(13) 0.8235(10) 0.6933(5) 0.0421(17) Uani 1 1 d . U . . .
H18 H 0.2787 0.8619 0.6423 0.051 Uiso 1 1 calc R U . . .
C19 C 0.2659(11) 0.7033(10) 0.7458(4) 0.0359(15) Uani 1 1 d . U . . .
H19 H 0.1348 0.6610 0.7304 0.043 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
S1 C5 1.726(7) . ?
S1 C2 1.771(7) . ?
O1 C12 1.457(8) . ?
O1 H1 0.8400 . ?
C1 C10 1.522(9) . ?
C1 C2 1.526(8) . ?
C1 C11 1.550(9) . ?
C1 C12 1.580(9) . ?
O2 C11 1.438(8) . ?
O2 H2 0.8400 . ?
C2 C3 1.652(9) . ?
C3 C4 1.605(9) . ?
C3 H3A 0.9900 . ?
C3 H3B 0.9900 . ?
C5 C4 1.379(11) . ?
C5 C6 1.410(11) . ?
C4 C9 1.427(10) . ?
C6 C7 1.371(12) . ?
C6 H6 0.9500 . ?
C7 C8 1.357(13) . ?
C7 H7 0.9500 . ?
C9 C8 1.380(12) . ?
C9 H9 0.9500 . ?
C8 H8 0.9500 . ?
C10 H10A 0.9800 . ?
C10 H10B 0.9800 . ?
C10 H10C 0.9800 . ?
C11 H11A 0.9900 . ?
C11 H11B 0.9900 . ?
C12 C13 1.514(9) . ?
C12 C14 1.526(9) . ?
C13 H13A 0.9800 . ?
C13 H13B 0.9800 . ?
C13 H13C 0.9800 . ?
C14 C19 1.388(9) . ?
C14 C15 1.396(9) . ?
C15 C16 1.394(10) . ?
C15 H15 0.9500 . ?
C16 C17 1.378(12) . ?
C16 H16 0.9500 . ?
C17 C18 1.380(13) . ?
C17 H17 0.9500 . ?
C18 C19 1.381(11) . ?
C18 H18 0.9500 . ?
C19 H19 0.9500 . ?

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
C5 S1 C2 90.1(3) . . ?
C12 O1 H1 109.5 . . ?
C10 C1 C2 109.7(5) . . ?
C10 C1 C11 108.1(5) . . ?
C2 C1 C11 105.6(5) . . ?
C10 C1 C12 110.5(6) . . ?
C2 C1 C12 111.9(5) . . ?
C11 C1 C12 110.8(5) . . ?
C11 O2 H2 109.5 . . ?
C1 C2 C3 121.3(5) . . ?
C1 C2 S1 118.9(4) . . ?
C3 C2 S1 119.7(4) . . ?
C4 C3 C2 93.2(5) . . ?
C4 C3 H3A 113.1 . . ?
C2 C3 H3A 113.1 . . ?
C4 C3 H3B 113.1 . . ?
C2 C3 H3B 113.1 . . ?
H3A C3 H3B 110.5 . . ?
C4 C5 C6 121.3(7) . . ?
C4 C5 S1 114.8(5) . . ?
C6 C5 S1 123.9(6) . . ?
C5 C4 C9 118.9(7) . . ?
C5 C4 C3 122.0(6) . . ?
C9 C4 C3 119.1(7) . . ?
C7 C6 C5 117.8(8) . . ?
C7 C6 H6 121.1 . . ?
C5 C6 H6 121.1 . . ?
C8 C7 C6 122.2(8) . . ?
C8 C7 H7 118.9 . . ?
C6 C7 H7 118.9 . . ?
C8 C9 C4 118.6(7) . . ?
C8 C9 H9 120.7 . . ?
C4 C9 H9 120.7 . . ?
C7 C8 C9 121.2(7) . . ?
C7 C8 H8 119.4 . . ?
C9 C8 H8 119.4 . . ?
C1 C10 H10A 109.5 . . ?
C1 C10 H10B 109.5 . . ?
H10A C10 H10B 109.5 . . ?
C1 C10 H10C 109.5 . . ?
H10A C10 H10C 109.5 . . ?
H10B C10 H10C 109.5 . . ?
O2 C11 C1 113.6(5) . . ?
O2 C11 H11A 108.8 . . ?
C1 C11 H11A 108.8 . . ?
O2 C11 H11B 108.8 . . ?
C1 C11 H11B 108.8 . . ?
H11A C11 H11B 107.7 . . ?
O1 C12 C13 103.7(5) . . ?
O1 C12 C14 109.8(5) . . ?
C13 C12 C14 110.5(6) . . ?
O1 C12 C1 107.4(5) . . ?
C13 C12 C1 113.2(5) . . ?
C14 C12 C1 111.8(5) . . ?
C12 C13 H13A 109.5 . . ?
C12 C13 H13B 109.5 . . ?
H13A C13 H13B 109.5 . . ?
C12 C13 H13C 109.5 . . ?
H13A C13 H13C 109.5 . . ?
H13B C13 H13C 109.5 . . ?
C19 C14 C15 117.3(7) . . ?
C19 C14 C12 122.1(6) . . ?
C15 C14 C12 120.6(6) . . ?
C16 C15 C14 121.0(6) . . ?
C16 C15 H15 119.5 . . ?
C14 C15 H15 119.5 . . ?
C17 C16 C15 119.9(7) . . ?
C17 C16 H16 120.1 . . ?
C15 C16 H16 120.1 . . ?
C16 C17 C18 120.3(7) . . ?
C16 C17 H17 119.9 . . ?
C18 C17 H17 119.9 . . ?
C17 C18 C19 119.3(7) . . ?
C17 C18 H18 120.3 . . ?
C19 C18 H18 120.3 . . ?
C18 C19 C14 122.3(7) . . ?
C18 C19 H19 118.9 . . ?
C14 C19 H19 118.9 . . ?

_refine_diff_density_max         1.824
_refine_diff_density_min         -0.411
_refine_diff_density_rms         0.093



####################################################################### 
# 
# 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_A
_audit_block_doi                 10.5517/ccdc.csd.cc1q0cz2
_database_code_depnum_ccdc_archive 'CCDC 1579294'
_audit_update_record             
;
2017-10-11 deposited with the CCDC.
2018-04-11 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C24 H27 B O4'
_chemical_formula_sum            'C24 H27 B O4'
_chemical_formula_weight         390.27

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 '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 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
B B 0.0090 0.0039 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      monoclinic
_space_group_IT_number           4
_space_group_name_H-M_alt        'P 21'
_space_group_name_Hall           'P 2yb'

_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'

_cell_length_a                   12.5495(6)
_cell_length_b                   6.3424(3)
_cell_length_c                   13.2506(6)
_cell_angle_alpha                90
_cell_angle_beta                 92.671(2)
_cell_angle_gamma                90
_cell_volume                     1053.52(9)
_cell_formula_units_Z            2
_cell_measurement_temperature    173(2)
_cell_measurement_reflns_used    9902
_cell_measurement_theta_min      3.34
_cell_measurement_theta_max      66.61

_exptl_crystal_description       block
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.230
_exptl_crystal_F_000             567
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.05
_exptl_crystal_size_mid          0.04
_exptl_crystal_size_min          0.03
_exptl_absorpt_coefficient_mu    0.652
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   none
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      173(2)
_diffrn_radiation_wavelength     1.54178
_diffrn_radiation_type           CuK\a
_diffrn_source                   'sealed tube'
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            13476
_diffrn_reflns_av_unetI/netI     0.0187
_diffrn_reflns_av_R_equivalents  0.0218
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_theta_min         3.339
_diffrn_reflns_theta_max         66.732
_diffrn_reflns_theta_full        66.732
_diffrn_measured_fraction_theta_max 0.992
_diffrn_measured_fraction_theta_full 0.992
_diffrn_reflns_Laue_measured_fraction_max 0.992
_diffrn_reflns_Laue_measured_fraction_full 0.992
_diffrn_reflns_point_group_measured_fraction_max 0.976
_diffrn_reflns_point_group_measured_fraction_full 0.976
_reflns_number_total             3646
_reflns_number_gt                3560
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.791
_reflns_Friedel_fraction_max     0.957
_reflns_Friedel_fraction_full    0.957

_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 (Sheldrick, 2014)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_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)+(0.0401P)²+0.1041P] 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_abs_structure_details 
;
 Flack x determined using 1546 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.06(5)
_chemical_absolute_configuration ad
_refine_ls_number_reflns         3646
_refine_ls_number_parameters     267
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0267
_refine_ls_R_factor_gt           0.0260
_refine_ls_wR_factor_ref         0.0682
_refine_ls_wR_factor_gt          0.0676
_refine_ls_goodness_of_fit_ref   1.057
_refine_ls_restrained_S_all      1.057
_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
B1 B 0.21932(15) 0.3931(3) 0.91323(14) 0.0310(4) Uani 1 1 d . . . . .
C1 C 0.27045(13) 0.6288(3) 0.75500(12) 0.0275(4) Uani 1 1 d . . . . .
C2 C 0.18592(13) 0.4981(3) 0.80899(12) 0.0306(4) Uani 1 1 d . . . . .
H2A H 0.1609 0.3847 0.7623 0.037 Uiso 1 1 calc R U . . .
H2B H 0.1241 0.5912 0.8197 0.037 Uiso 1 1 calc R U . . .
C3 C 0.22079(12) 0.7140(3) 0.65829(12) 0.0269(3) Uani 1 1 d . . . . .
C4 C 0.30525(18) 0.3158(3) 1.06361(14) 0.0422(5) Uani 1 1 d . . . . .
C5 C 0.19478(18) 0.2056(3) 1.05616(14) 0.0432(5) Uani 1 1 d . . . . .
C6 C 0.1089(2) 0.3247(5) 1.11062(18) 0.0647(7) Uani 1 1 d . . . . .
H6A H 0.1110 0.4742 1.0921 0.097 Uiso 1 1 calc R U . . .
H6B H 0.1219 0.3102 1.1838 0.097 Uiso 1 1 calc R U . . .
H6C H 0.0387 0.2663 1.0909 0.097 Uiso 1 1 calc R U . . .
C7 C 0.1951(2) -0.0257(4) 1.08613(16) 0.0568(6) Uani 1 1 d . . . . .
H7A H 0.1224 -0.0818 1.0788 0.085 Uiso 1 1 calc R U . . .
H7B H 0.2215 -0.0398 1.1566 0.085 Uiso 1 1 calc R U . . .
H7C H 0.2416 -0.1047 1.0423 0.085 Uiso 1 1 calc R U . . .
C8 C 0.39747(18) 0.1710(4) 1.03920(17) 0.0534(6) Uani 1 1 d . . . . .
H8A H 0.3798 0.0949 0.9763 0.080 Uiso 1 1 calc R U . . .
H8B H 0.4100 0.0698 1.0943 0.080 Uiso 1 1 calc R U . . .
H8C H 0.4620 0.2554 1.0313 0.080 Uiso 1 1 calc R U . . .
C9 C 0.3315(2) 0.4351(4) 1.16141(16) 0.0635(7) Uani 1 1 d . . . . .
H9A H 0.3996 0.5089 1.1563 0.095 Uiso 1 1 calc R U . . .
H9B H 0.3367 0.3354 1.2179 0.095 Uiso 1 1 calc R U . . .
H9C H 0.2749 0.5378 1.1729 0.095 Uiso 1 1 calc R U . . .
C10 C 0.30917(15) 0.8131(3) 0.82261(13) 0.0329(4) Uani 1 1 d . . . . .
H10A H 0.3557 0.9050 0.7847 0.049 Uiso 1 1 calc R U . . .
H10B H 0.3489 0.7578 0.8823 0.049 Uiso 1 1 calc R U . . .
H10C H 0.2476 0.8939 0.8439 0.049 Uiso 1 1 calc R U . . .
C11 C 0.36607(13) 0.4848(3) 0.73487(12) 0.0297(4) Uani 1 1 d . . . . .
C12 C 0.45941(12) 0.5630(3) 0.67855(12) 0.0284(3) Uani 1 1 d . . . . .
C13 C 0.46174(14) 0.7561(3) 0.62779(13) 0.0311(4) Uani 1 1 d . . . . .
H13 H 0.4025 0.8490 0.6296 0.037 Uiso 1 1 calc R U . . .
C14 C 0.55019(14) 0.8127(3) 0.57470(13) 0.0352(4) Uani 1 1 d . . . . .
H14 H 0.5511 0.9440 0.5402 0.042 Uiso 1 1 calc R U . . .
C15 C 0.63666(14) 0.6792(3) 0.57185(14) 0.0386(4) Uani 1 1 d . . . . .
H15 H 0.6966 0.7178 0.5346 0.046 Uiso 1 1 calc R U . . .
C16 C 0.63632(14) 0.4892(3) 0.62312(14) 0.0393(4) Uani 1 1 d . . . . .
H16 H 0.6965 0.3986 0.6220 0.047 Uiso 1 1 calc R U . . .
C17 C 0.54851(14) 0.4308(3) 0.67598(13) 0.0347(4) Uani 1 1 d . . . . .
H17 H 0.5487 0.2999 0.7108 0.042 Uiso 1 1 calc R U . . .
C18 C 0.17832(12) 0.9022(3) 0.63337(13) 0.0287(3) Uani 1 1 d . . . . .
H18 H 0.1751 1.0224 0.6759 0.034 Uiso 1 1 calc R U . . .
C19 C 0.13855(12) 0.8874(3) 0.52986(12) 0.0280(3) Uani 1 1 d . . . . .
C20 C 0.08689(13) 1.0250(3) 0.46120(14) 0.0339(4) Uani 1 1 d . . . . .
H20 H 0.0705 1.1655 0.4799 0.041 Uiso 1 1 calc R U . . .
C21 C 0.06052(13) 0.9507(3) 0.36540(14) 0.0385(4) Uani 1 1 d . . . . .
H21 H 0.0254 1.0419 0.3177 0.046 Uiso 1 1 calc R U . . .
C22 C 0.08437(15) 0.7433(3) 0.33667(14) 0.0387(4) Uani 1 1 d . . . . .
H22 H 0.0647 0.6971 0.2702 0.046 Uiso 1 1 calc R U . . .
C23 C 0.13615(13) 0.6047(3) 0.40375(13) 0.0337(4) Uani 1 1 d . . . . .
H23 H 0.1534 0.4647 0.3849 0.040 Uiso 1 1 calc R U . . .
C24 C 0.16114(12) 0.6821(3) 0.49935(12) 0.0281(4) Uani 1 1 d . . . . .
O1 O 0.29476(11) 0.4691(2) 0.98135(9) 0.0389(3) Uani 1 1 d . . . . .
O2 O 0.16551(10) 0.2224(2) 0.94809(9) 0.0389(3) Uani 1 1 d . . . . .
O3 O 0.21128(8) 0.57253(18) 0.57813(8) 0.0280(3) Uani 1 1 d . . . . .
O4 O 0.36714(11) 0.3064(2) 0.76832(12) 0.0474(4) 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
B1 O1 1.365(2) . ?
B1 O2 1.368(2) . ?
B1 C2 1.573(2) . ?
C1 C3 1.499(2) . ?
C1 C10 1.537(2) . ?
C1 C11 1.541(2) . ?
C1 C2 1.548(2) . ?
C2 H2A 0.9900 . ?
C2 H2B 0.9900 . ?
C3 C18 1.343(2) . ?
C3 O3 1.391(2) . ?
C4 O1 1.462(2) . ?
C4 C9 1.523(3) . ?
C4 C8 1.524(3) . ?
C4 C5 1.551(3) . ?
C5 O2 1.466(2) . ?
C5 C7 1.520(3) . ?
C5 C6 1.525(3) . ?
C6 H6A 0.9800 . ?
C6 H6B 0.9800 . ?
C6 H6C 0.9800 . ?
C7 H7A 0.9800 . ?
C7 H7B 0.9800 . ?
C7 H7C 0.9800 . ?
C8 H8A 0.9800 . ?
C8 H8B 0.9800 . ?
C8 H8C 0.9800 . ?
C9 H9A 0.9800 . ?
C9 H9B 0.9800 . ?
C9 H9C 0.9800 . ?
C10 H10A 0.9800 . ?
C10 H10B 0.9800 . ?
C10 H10C 0.9800 . ?
C11 O4 1.215(2) . ?
C11 C12 1.502(2) . ?
C12 C13 1.398(2) . ?
C12 C17 1.399(2) . ?
C13 C14 1.389(2) . ?
C13 H13 0.9500 . ?
C14 C15 1.378(3) . ?
C14 H14 0.9500 . ?
C15 C16 1.384(3) . ?
C15 H15 0.9500 . ?
C16 C17 1.384(3) . ?
C16 H16 0.9500 . ?
C17 H17 0.9500 . ?
C18 C19 1.441(2) . ?
C18 H18 0.9500 . ?
C19 C24 1.397(3) . ?
C19 C20 1.398(2) . ?
C20 C21 1.380(3) . ?
C20 H20 0.9500 . ?
C21 C22 1.405(3) . ?
C21 H21 0.9500 . ?
C22 C23 1.390(3) . ?
C22 H22 0.9500 . ?
C23 C24 1.381(2) . ?
C23 H23 0.9500 . ?
C24 O3 1.3810(19) . ?

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 B1 O2 113.22(15) . . ?
O1 B1 C2 125.42(16) . . ?
O2 B1 C2 121.08(16) . . ?
C3 C1 C10 109.38(14) . . ?
C3 C1 C11 111.19(13) . . ?
C10 C1 C11 108.90(13) . . ?
C3 C1 C2 108.76(13) . . ?
C10 C1 C2 110.04(13) . . ?
C11 C1 C2 108.57(13) . . ?
C1 C2 B1 118.19(14) . . ?
C1 C2 H2A 107.8 . . ?
B1 C2 H2A 107.8 . . ?
C1 C2 H2B 107.8 . . ?
B1 C2 H2B 107.8 . . ?
H2A C2 H2B 107.1 . . ?
C18 C3 O3 111.52(14) . . ?
C18 C3 C1 132.45(16) . . ?
O3 C3 C1 115.96(14) . . ?
O1 C4 C9 108.18(17) . . ?
O1 C4 C8 106.58(16) . . ?
C9 C4 C8 110.11(18) . . ?
O1 C4 C5 101.71(15) . . ?
C9 C4 C5 115.76(19) . . ?
C8 C4 C5 113.62(18) . . ?
O2 C5 C7 108.84(17) . . ?
O2 C5 C6 106.02(17) . . ?
C7 C5 C6 110.3(2) . . ?
O2 C5 C4 102.24(14) . . ?
C7 C5 C4 115.3(2) . . ?
C6 C5 C4 113.3(2) . . ?
C5 C6 H6A 109.5 . . ?
C5 C6 H6B 109.5 . . ?
H6A C6 H6B 109.5 . . ?
C5 C6 H6C 109.5 . . ?
H6A C6 H6C 109.5 . . ?
H6B C6 H6C 109.5 . . ?
C5 C7 H7A 109.5 . . ?
C5 C7 H7B 109.5 . . ?
H7A C7 H7B 109.5 . . ?
C5 C7 H7C 109.5 . . ?
H7A C7 H7C 109.5 . . ?
H7B C7 H7C 109.5 . . ?
C4 C8 H8A 109.5 . . ?
C4 C8 H8B 109.5 . . ?
H8A C8 H8B 109.5 . . ?
C4 C8 H8C 109.5 . . ?
H8A C8 H8C 109.5 . . ?
H8B C8 H8C 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 . . ?
C1 C10 H10A 109.5 . . ?
C1 C10 H10B 109.5 . . ?
H10A C10 H10B 109.5 . . ?
C1 C10 H10C 109.5 . . ?
H10A C10 H10C 109.5 . . ?
H10B C10 H10C 109.5 . . ?
O4 C11 C12 119.55(16) . . ?
O4 C11 C1 118.96(15) . . ?
C12 C11 C1 121.44(14) . . ?
C13 C12 C17 118.59(15) . . ?
C13 C12 C11 124.24(15) . . ?
C17 C12 C11 117.16(16) . . ?
C14 C13 C12 120.37(16) . . ?
C14 C13 H13 119.8 . . ?
C12 C13 H13 119.8 . . ?
C15 C14 C13 120.25(18) . . ?
C15 C14 H14 119.9 . . ?
C13 C14 H14 119.9 . . ?
C14 C15 C16 120.07(17) . . ?
C14 C15 H15 120.0 . . ?
C16 C15 H15 120.0 . . ?
C17 C16 C15 120.18(17) . . ?
C17 C16 H16 119.9 . . ?
C15 C16 H16 119.9 . . ?
C16 C17 C12 120.53(17) . . ?
C16 C17 H17 119.7 . . ?
C12 C17 H17 119.7 . . ?
C3 C18 C19 106.98(15) . . ?
C3 C18 H18 126.5 . . ?
C19 C18 H18 126.5 . . ?
C24 C19 C20 119.21(16) . . ?
C24 C19 C18 105.70(14) . . ?
C20 C19 C18 135.10(17) . . ?
C21 C20 C19 117.99(18) . . ?
C21 C20 H20 121.0 . . ?
C19 C20 H20 121.0 . . ?
C20 C21 C22 121.61(17) . . ?
C20 C21 H21 119.2 . . ?
C22 C21 H21 119.2 . . ?
C23 C22 C21 121.20(17) . . ?
C23 C22 H22 119.4 . . ?
C21 C22 H22 119.4 . . ?
C24 C23 C22 116.18(18) . . ?
C24 C23 H23 121.9 . . ?
C22 C23 H23 121.9 . . ?
C23 C24 O3 126.19(17) . . ?
C23 C24 C19 123.82(16) . . ?
O3 C24 C19 109.99(14) . . ?
B1 O1 C4 107.08(15) . . ?
B1 O2 C5 106.40(14) . . ?
C24 O3 C3 105.81(13) . . ?

_refine_diff_density_max         0.122
_refine_diff_density_min         -0.136
_refine_diff_density_rms         0.029



