# Electronic Supplementary Material (ESI) for ChemComm.
# This journal is © The Royal Society of Chemistry 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_shelxl
_database_code_depnum_ccdc_archive 'CCDC 911403'
_audit_update_record             
;
2012-11-19 deposited with the CCDC.
2016-07-06 downloaded from the CCDC.
;
#TrackingRef 'wts-2.cif'


_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C21 H19 B O2'
_chemical_formula_weight         314.17

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'
B B 0.0090 0.0039 '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'

_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_H-M   'P 21/a'

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

_cell_length_a                   14.9097(4)
_cell_length_b                   6.6345(2)
_cell_length_c                   16.6553(4)
_cell_angle_alpha                90.00
_cell_angle_beta                 92.822(2)
_cell_angle_gamma                90.00
_cell_volume                     1645.52(8)
_cell_formula_units_Z            4
_cell_measurement_temperature    290(2)
_cell_measurement_reflns_used    4221
_cell_measurement_theta_min      3.8821
_cell_measurement_theta_max      62.6143

_exptl_crystal_description       ?
_exptl_crystal_colour            ?
_exptl_crystal_size_max          0.39
_exptl_crystal_size_mid          0.35
_exptl_crystal_size_min          0.30
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.268
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             664
_exptl_absorpt_coefficient_mu    0.620
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.7941
_exptl_absorpt_correction_T_max  0.8359
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.21 (release 14-08-2012 CrysAlis171 .NET)
(compiled Sep 14 2012,17:21:16)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;

_exptl_special_details           
;
?
;

_diffrn_ambient_temperature      290(2)
_diffrn_radiation_wavelength     1.54184
_diffrn_radiation_type           CuK\a
_diffrn_radiation_source         'Enhance Ultra (Cu) X-ray Source'
_diffrn_radiation_monochromator  mirror
_diffrn_measurement_device_type  'Gemini S Ultra, Agilent Technologies'
_diffrn_measurement_method       'ω scans'
_diffrn_detector_area_resol_mean 15.9149
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            8630
_diffrn_reflns_av_R_equivalents  0.0262
_diffrn_reflns_av_sigmaI/netI    0.0229
_diffrn_reflns_limit_h_min       -17
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_theta_min         6.39
_diffrn_reflns_theta_max         62.71
_reflns_number_total             2626
_reflns_number_gt                2239
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'CrysAlisPro (Agilent Technologies)'
_computing_cell_refinement       'CrysAlisPro (Agilent Technologies)'
_computing_data_reduction        'CrysAlisPro (Agilent Technologies)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1997)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    'Ortep-3 (L. J. Farrugia, 2001)'
_computing_publication_material  SHELXL-97

_refine_special_details          
;
Refinement of F² against ALL reflections. The weighted R-factor wR and
goodness of fit S are based on F², conventional R-factors R are based
on F, with F set to zero for negative F². The threshold expression of
F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is
not relevant to the choice of reflections for refinement. R-factors based
on F² are statistically about twice as large as those based on F, and R-
factors based on ALL data will be even larger.
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0840P)²+0.1181P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         2626
_refine_ls_number_parameters     219
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0520
_refine_ls_R_factor_gt           0.0457
_refine_ls_wR_factor_ref         0.1389
_refine_ls_wR_factor_gt          0.1299
_refine_ls_goodness_of_fit_ref   1.048
_refine_ls_restrained_S_all      1.048
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
O2 O 0.87080(7) 0.38114(17) 0.71134(6) 0.0698(3) Uani 1 1 d . . .
C10 C 0.73912(8) 0.9372(2) 0.81381(8) 0.0522(4) Uani 1 1 d . . .
C11 C 0.78544(8) 0.7653(2) 0.78596(8) 0.0507(3) Uani 1 1 d . . .
O1 O 0.73291(7) 0.3358(2) 0.63800(8) 0.0859(4) Uani 1 1 d . . .
C16 C 0.60644(9) 0.8359(3) 0.73449(10) 0.0684(5) Uani 1 1 d . . .
H16 H 0.5469 0.8561 0.7172 0.082 Uiso 1 1 calc R . .
C4 C 0.87397(9) 1.0472(2) 0.89383(8) 0.0559(4) Uani 1 1 d . . .
C9 C 0.64770(9) 0.9716(2) 0.78794(9) 0.0604(4) Uani 1 1 d . . .
C5 C 0.78318(9) 1.0789(2) 0.86678(8) 0.0530(4) Uani 1 1 d . . .
C12 C 0.87669(9) 0.7378(2) 0.81632(8) 0.0555(4) Uani 1 1 d . . .
H12 H 0.9081 0.6245 0.8006 0.067 Uiso 1 1 calc R . .
C3 C 0.91542(11) 1.1885(3) 0.94558(9) 0.0662(4) Uani 1 1 d . . .
H3 H 0.9749 1.1692 0.9634 0.079 Uiso 1 1 calc R . .
C14 C 0.74217(9) 0.6303(2) 0.73063(9) 0.0558(4) Uani 1 1 d . . .
C13 C 0.91802(9) 0.8712(2) 0.86677(9) 0.0584(4) Uani 1 1 d . . .
H13 H 0.9772 0.8474 0.8845 0.070 Uiso 1 1 calc R . .
C6 C 0.73731(10) 1.2531(2) 0.89291(9) 0.0613(4) Uani 1 1 d . . .
C8 C 0.60287(11) 1.1462(3) 0.81690(10) 0.0715(5) Uani 1 1 d . . .
H8 H 0.5428 1.1671 0.8016 0.086 Uiso 1 1 calc R . .
C2 C 0.86995(12) 1.3560(3) 0.97077(10) 0.0729(5) Uani 1 1 d . . .
H2 H 0.8986 1.4474 1.0057 0.088 Uiso 1 1 calc R . .
C18 C 0.86596(11) 0.1560(2) 0.59440(9) 0.0655(4) Uani 1 1 d . . .
C19 C 0.90616(11) 0.2008(3) 0.67733(10) 0.0703(5) Uani 1 1 d . . .
H19A H 0.8946 0.0880 0.7124 0.084 Uiso 1 1 calc R . .
H19B H 0.9707 0.2143 0.6746 0.084 Uiso 1 1 calc R . .
C15 C 0.65227(9) 0.6720(3) 0.70672(10) 0.0656(4) Uani 1 1 d . . .
H15 H 0.6225 0.5850 0.6706 0.079 Uiso 1 1 calc R . .
C7 C 0.64534(11) 1.2800(3) 0.86538(10) 0.0712(5) Uani 1 1 d . . .
H7 H 0.6144 1.3934 0.8817 0.085 Uiso 1 1 calc R . .
B1 B 0.78537(11) 0.4392(3) 0.69233(10) 0.0585(4) Uani 1 1 d . . .
C21 C 0.89614(14) -0.0535(3) 0.56933(12) 0.0859(5) Uani 1 1 d . . .
H21A H 0.8739 -0.1521 0.6056 0.129 Uiso 1 1 calc R . .
H21B H 0.9605 -0.0588 0.5709 0.129 Uiso 1 1 calc R . .
H21C H 0.8729 -0.0816 0.5157 0.129 Uiso 1 1 calc R . .
C1 C 0.78175(12) 1.3886(3) 0.94423(9) 0.0700(5) Uani 1 1 d . . .
H1 H 0.7519 1.5030 0.9611 0.084 Uiso 1 1 calc R . .
C20 C 0.89405(17) 0.3132(3) 0.53470(12) 0.1002(7) Uani 1 1 d . . .
H20A H 0.8689 0.2801 0.4822 0.150 Uiso 1 1 calc R . .
H20B H 0.9584 0.3159 0.5337 0.150 Uiso 1 1 calc R . .
H20C H 0.8727 0.4431 0.5504 0.150 Uiso 1 1 calc R . .
C17 C 0.76505(12) 0.1557(3) 0.60192(13) 0.0842(5) Uani 1 1 d . . .
H17A H 0.7360 0.1404 0.5489 0.101 Uiso 1 1 calc R . .
H17B H 0.7486 0.0407 0.6340 0.101 Uiso 1 1 calc R . .


_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 B1 1.353(2) . ?
O2 C19 1.4353(18) . ?
C10 C11 1.423(2) . ?
C10 C5 1.427(2) . ?
C10 C9 1.4274(19) . ?
C11 C14 1.417(2) . ?
C11 C12 1.4396(19) . ?
O1 B1 1.353(2) . ?
O1 C17 1.431(2) . ?
C16 C15 1.377(2) . ?
C16 C9 1.388(2) . ?
C16 H16 0.9300 . ?
C4 C3 1.397(2) . ?
C4 C5 1.4212(19) . ?
C4 C13 1.424(2) . ?
C9 C8 1.433(2) . ?
C5 C6 1.422(2) . ?
C12 C13 1.348(2) . ?
C12 H12 0.9300 . ?
C3 C2 1.378(2) . ?
C3 H3 0.9300 . ?
C14 C15 1.407(2) . ?
C14 B1 1.572(2) . ?
C13 H13 0.9300 . ?
C6 C1 1.386(2) . ?
C6 C7 1.436(2) . ?
C8 C7 1.338(3) . ?
C8 H8 0.9300 . ?
C2 C1 1.384(2) . ?
C2 H2 0.9300 . ?
C18 C19 1.508(2) . ?
C18 C20 1.514(3) . ?
C18 C17 1.516(2) . ?
C18 C21 1.526(2) . ?
C19 H19A 0.9700 . ?
C19 H19B 0.9700 . ?
C15 H15 0.9300 . ?
C7 H7 0.9300 . ?
C21 H21A 0.9600 . ?
C21 H21B 0.9600 . ?
C21 H21C 0.9600 . ?
C1 H1 0.9300 . ?
C20 H20A 0.9600 . ?
C20 H20B 0.9600 . ?
C20 H20C 0.9600 . ?
C17 H17A 0.9700 . ?
C17 H17B 0.9700 . ?

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
B1 O2 C19 120.31(12) . . ?
C11 C10 C5 120.91(12) . . ?
C11 C10 C9 120.08(13) . . ?
C5 C10 C9 119.00(13) . . ?
C14 C11 C10 120.39(12) . . ?
C14 C11 C12 122.72(13) . . ?
C10 C11 C12 116.90(13) . . ?
B1 O1 C17 120.63(13) . . ?
C15 C16 C9 121.07(13) . . ?
C15 C16 H16 119.5 . . ?
C9 C16 H16 119.5 . . ?
C3 C4 C5 118.80(14) . . ?
C3 C4 C13 123.29(13) . . ?
C5 C4 C13 117.90(13) . . ?
C16 C9 C10 118.45(14) . . ?
C16 C9 C8 122.73(14) . . ?
C10 C9 C8 118.81(15) . . ?
C4 C5 C6 119.22(14) . . ?
C4 C5 C10 120.05(13) . . ?
C6 C5 C10 120.73(13) . . ?
C13 C12 C11 122.07(13) . . ?
C13 C12 H12 119.0 . . ?
C11 C12 H12 119.0 . . ?
C2 C3 C4 121.32(15) . . ?
C2 C3 H3 119.3 . . ?
C4 C3 H3 119.3 . . ?
C15 C14 C11 117.18(14) . . ?
C15 C14 B1 116.58(14) . . ?
C11 C14 B1 126.24(12) . . ?
C12 C13 C4 122.13(13) . . ?
C12 C13 H13 118.9 . . ?
C4 C13 H13 118.9 . . ?
C1 C6 C5 119.56(14) . . ?
C1 C6 C7 122.44(15) . . ?
C5 C6 C7 117.99(15) . . ?
C7 C8 C9 121.65(14) . . ?
C7 C8 H8 119.2 . . ?
C9 C8 H8 119.2 . . ?
C3 C2 C1 120.21(15) . . ?
C3 C2 H2 119.9 . . ?
C1 C2 H2 119.9 . . ?
C19 C18 C20 110.83(15) . . ?
C19 C18 C17 106.02(14) . . ?
C20 C18 C17 111.29(16) . . ?
C19 C18 C21 108.71(14) . . ?
C20 C18 C21 110.67(14) . . ?
C17 C18 C21 109.18(14) . . ?
O2 C19 C18 112.86(13) . . ?
O2 C19 H19A 109.0 . . ?
C18 C19 H19A 109.0 . . ?
O2 C19 H19B 109.0 . . ?
C18 C19 H19B 109.0 . . ?
H19A C19 H19B 107.8 . . ?
C16 C15 C14 122.81(15) . . ?
C16 C15 H15 118.6 . . ?
C14 C15 H15 118.6 . . ?
C8 C7 C6 121.78(15) . . ?
C8 C7 H7 119.1 . . ?
C6 C7 H7 119.1 . . ?
O2 B1 O1 121.25(15) . . ?
O2 B1 C14 122.31(13) . . ?
O1 B1 C14 116.43(13) . . ?
C18 C21 H21A 109.5 . . ?
C18 C21 H21B 109.5 . . ?
H21A C21 H21B 109.5 . . ?
C18 C21 H21C 109.5 . . ?
H21A C21 H21C 109.5 . . ?
H21B C21 H21C 109.5 . . ?
C2 C1 C6 120.89(15) . . ?
C2 C1 H1 119.6 . . ?
C6 C1 H1 119.6 . . ?
C18 C20 H20A 109.5 . . ?
C18 C20 H20B 109.5 . . ?
H20A C20 H20B 109.5 . . ?
C18 C20 H20C 109.5 . . ?
H20A C20 H20C 109.5 . . ?
H20B C20 H20C 109.5 . . ?
O1 C17 C18 112.82(14) . . ?
O1 C17 H17A 109.0 . . ?
C18 C17 H17A 109.0 . . ?
O1 C17 H17B 109.0 . . ?
C18 C17 H17B 109.0 . . ?
H17A C17 H17B 107.8 . . ?

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
C5 C10 C11 C14 -177.24(12) . . . . ?
C9 C10 C11 C14 1.8(2) . . . . ?
C5 C10 C11 C12 2.51(19) . . . . ?
C9 C10 C11 C12 -178.39(12) . . . . ?
C15 C16 C9 C10 -0.1(2) . . . . ?
C15 C16 C9 C8 178.66(14) . . . . ?
C11 C10 C9 C16 -1.1(2) . . . . ?
C5 C10 C9 C16 178.06(13) . . . . ?
C11 C10 C9 C8 -179.88(13) . . . . ?
C5 C10 C9 C8 -0.8(2) . . . . ?
C3 C4 C5 C6 0.1(2) . . . . ?
C13 C4 C5 C6 179.86(12) . . . . ?
C3 C4 C5 C10 179.93(12) . . . . ?
C13 C4 C5 C10 -0.35(19) . . . . ?
C11 C10 C5 C4 -1.3(2) . . . . ?
C9 C10 C5 C4 179.55(12) . . . . ?
C11 C10 C5 C6 178.44(11) . . . . ?
C9 C10 C5 C6 -0.7(2) . . . . ?
C14 C11 C12 C13 177.64(13) . . . . ?
C10 C11 C12 C13 -2.1(2) . . . . ?
C5 C4 C3 C2 0.3(2) . . . . ?
C13 C4 C3 C2 -179.45(14) . . . . ?
C10 C11 C14 C15 -1.4(2) . . . . ?
C12 C11 C14 C15 178.84(13) . . . . ?
C10 C11 C14 B1 177.75(13) . . . . ?
C12 C11 C14 B1 -2.0(2) . . . . ?
C11 C12 C13 C4 0.5(2) . . . . ?
C3 C4 C13 C12 -179.50(14) . . . . ?
C5 C4 C13 C12 0.8(2) . . . . ?
C4 C5 C6 C1 -0.1(2) . . . . ?
C10 C5 C6 C1 -179.86(13) . . . . ?
C4 C5 C6 C7 -179.28(12) . . . . ?
C10 C5 C6 C7 0.9(2) . . . . ?
C16 C9 C8 C7 -176.75(15) . . . . ?
C10 C9 C8 C7 2.0(2) . . . . ?
C4 C3 C2 C1 -0.7(2) . . . . ?
B1 O2 C19 C18 31.1(2) . . . . ?
C20 C18 C19 O2 67.17(18) . . . . ?
C17 C18 C19 O2 -53.73(19) . . . . ?
C21 C18 C19 O2 -170.99(14) . . . . ?
C9 C16 C15 C14 0.5(2) . . . . ?
C11 C14 C15 C16 0.2(2) . . . . ?
B1 C14 C15 C16 -179.01(14) . . . . ?
C9 C8 C7 C6 -1.8(3) . . . . ?
C1 C6 C7 C8 -178.88(15) . . . . ?
C5 C6 C7 C8 0.3(2) . . . . ?
C19 O2 B1 O1 -3.5(2) . . . . ?
C19 O2 B1 C14 177.41(13) . . . . ?
C17 O1 B1 O2 3.1(3) . . . . ?
C17 O1 B1 C14 -177.78(15) . . . . ?
C15 C14 B1 O2 -178.94(14) . . . . ?
C11 C14 B1 O2 1.9(2) . . . . ?
C15 C14 B1 O1 2.0(2) . . . . ?
C11 C14 B1 O1 -177.22(14) . . . . ?
C3 C2 C1 C6 0.8(2) . . . . ?
C5 C6 C1 C2 -0.4(2) . . . . ?
C7 C6 C1 C2 178.78(14) . . . . ?
B1 O1 C17 C18 -30.1(2) . . . . ?
C19 C18 C17 O1 53.3(2) . . . . ?
C20 C18 C17 O1 -67.3(2) . . . . ?
C21 C18 C17 O1 170.21(15) . . . . ?

_diffrn_measured_fraction_theta_max 0.993
_diffrn_reflns_theta_full        62.71
_diffrn_measured_fraction_theta_full 0.993
_refine_diff_density_max         0.167
_refine_diff_density_min         -0.162
_refine_diff_density_rms         0.030
####################################################################### 
# 
# 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_shelxl2
_database_code_depnum_ccdc_archive 'CCDC 911404'
_audit_update_record             
;
2012-11-19 deposited with the CCDC.
2016-07-06 downloaded from the CCDC.
;
#TrackingRef 'wts1.cif'


_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C22 H21 B O2'
_chemical_formula_weight         328.20

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'
B B 0.0013 0.0007 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_H-M   'P 21/c'

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

_cell_length_a                   11.7096(13)
_cell_length_b                   10.8168(11)
_cell_length_c                   14.2151(15)
_cell_angle_alpha                90.00
_cell_angle_beta                 91.551(10)
_cell_angle_gamma                90.00
_cell_volume                     1799.8(3)
_cell_formula_units_Z            4
_cell_measurement_temperature    290(2)
_cell_measurement_reflns_used    2575
_cell_measurement_theta_min      3.3068
_cell_measurement_theta_max      29.0397

_exptl_crystal_description       ?
_exptl_crystal_colour            ?
_exptl_crystal_size_max          0.42
_exptl_crystal_size_mid          0.38
_exptl_crystal_size_min          0.32
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.211
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             696
_exptl_absorpt_coefficient_mu    0.075
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.9692
_exptl_absorpt_correction_T_max  0.9764
_exptl_absorpt_process_details   
;
CrysAlisPro, Oxford Diffraction Ltd.,
Version 1.171.34.40 (release 27-08-2010 CrysAlis171 .NET)
(compiled Aug 27 2010,11:50:40)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;

_exptl_special_details           
;
?
;

_diffrn_ambient_temperature      290(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'Enhance (Mo) X-ray Source'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Xcalibur, Sapphire3, Gemini ultra'
_diffrn_measurement_method       'ω scans'
_diffrn_detector_area_resol_mean 15.9149
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            8407
_diffrn_reflns_av_R_equivalents  0.0327
_diffrn_reflns_av_sigmaI/netI    0.0386
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_theta_min         3.31
_diffrn_reflns_theta_max         26.37
_reflns_number_total             3638
_reflns_number_gt                2137
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'CrysAlisPro (Oxford Diffraction Ltd.)'
_computing_cell_refinement       'CrysAlisPro (Oxford Diffraction Ltd.)'
_computing_data_reduction        'CrysAlisPro (Oxford Diffraction Ltd.)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1997)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    'Ortep-3 (L. J. Farrugia, 2001)'
_computing_publication_material  SHELXL-97

_refine_special_details          
;
Refinement of F² against ALL reflections. The weighted R-factor wR and
goodness of fit S are based on F², conventional R-factors R are based
on F, with F set to zero for negative F². The threshold expression of
F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is
not relevant to the choice of reflections for refinement. R-factors based
on F² are statistically about twice as large as those based on F, and R-
factors based on ALL data will be even larger.
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0258P)²+0.8713P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         3638
_refine_ls_number_parameters     230
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.1076
_refine_ls_R_factor_gt           0.0627
_refine_ls_wR_factor_ref         0.1360
_refine_ls_wR_factor_gt          0.1164
_refine_ls_goodness_of_fit_ref   1.009
_refine_ls_restrained_S_all      1.010
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
O1 O 0.07211(14) 0.11781(17) 0.40496(12) 0.0775(6) Uani 1 1 d . . .
O2 O 0.05553(15) 0.23300(19) 0.27453(13) 0.0938(7) Uani 1 1 d . . .
C16 C 0.24029(17) 0.10161(19) 0.29724(15) 0.0498(5) Uani 1 1 d . . .
C9 C 0.29786(17) 0.13286(19) 0.21446(15) 0.0475(5) Uani 1 1 d . . .
C4 C 0.47083(18) 0.1221(2) 0.11908(17) 0.0540(6) Uani 1 1 d . . .
C10 C 0.41073(17) 0.08809(19) 0.20087(15) 0.0500(5) Uani 1 1 d . . .
C8 C 0.24710(19) 0.2078(2) 0.14085(16) 0.0564(6) Uani 1 1 d . . .
H8 H 0.1731 0.2372 0.1476 0.068 Uiso 1 1 calc R . .
C11 C 0.46360(18) 0.0088(2) 0.26890(17) 0.0576(6) Uani 1 1 d . . .
C5 C 0.4179(2) 0.1967(2) 0.04836(17) 0.0586(6) Uani 1 1 d . . .
C7 C 0.3035(2) 0.2368(2) 0.06254(17) 0.0619(6) Uani 1 1 d . . .
H7 H 0.2668 0.2843 0.0163 0.074 Uiso 1 1 calc R . .
C15 C 0.29501(19) 0.0215(2) 0.36129(16) 0.0576(6) Uani 1 1 d . . .
H15 H 0.2570 -0.0013 0.4152 0.069 Uiso 1 1 calc R . .
C14 C 0.4025(2) -0.0247(2) 0.34777(17) 0.0642(7) Uani 1 1 d . . .
H14 H 0.4350 -0.0789 0.3917 0.077 Uiso 1 1 calc R . .
C2 C 0.6400(2) 0.1114(3) 0.0247(2) 0.0824(9) Uani 1 1 d . . .
H2 H 0.7138 0.0830 0.0155 0.099 Uiso 1 1 calc R . .
C12 C 0.5768(2) -0.0337(3) 0.2533(2) 0.0758(8) Uani 1 1 d . . .
H12 H 0.6120 -0.0857 0.2974 0.091 Uiso 1 1 calc R . .
C1 C 0.5879(3) 0.1853(3) -0.0423(2) 0.0833(9) Uani 1 1 d . . .
H1 H 0.6273 0.2070 -0.0958 0.100 Uiso 1 1 calc R . .
C3 C 0.5836(2) 0.0782(2) 0.10625(19) 0.0658(7) Uani 1 1 d . . .
C18 C -0.0431(2) 0.1696(3) 0.40613(18) 0.0689(7) Uani 1 1 d U . .
C6 C 0.4782(2) 0.2278(2) -0.03146(18) 0.0727(7) Uani 1 1 d . . .
H6 H 0.4442 0.2776 -0.0776 0.087 Uiso 1 1 calc R . .
C13 C 0.6336(2) -0.0009(3) 0.1771(2) 0.0800(8) Uani 1 1 d . . .
H13 H 0.7076 -0.0300 0.1698 0.096 Uiso 1 1 calc R . .
C17 C -0.0399(2) 0.2713(3) 0.3315(2) 0.0851(9) Uani 1 1 d . . .
C20 C -0.1253(2) 0.0645(3) 0.3782(2) 0.1019(10) Uani 1 1 d U . .
H20B H -0.2027 0.0921 0.3840 0.153 Uiso 1 1 calc R . .
H20C H -0.1117 -0.0051 0.4188 0.153 Uiso 1 1 calc R . .
H20A H -0.1128 0.0407 0.3142 0.153 Uiso 1 1 calc R . .
C19 C -0.0649(3) 0.2087(3) 0.50582(18) 0.0944(10) Uani 1 1 d . . .
H19C H -0.0074 0.2667 0.5263 0.142 Uiso 1 1 calc R . .
H19B H -0.0625 0.1375 0.5462 0.142 Uiso 1 1 calc R . .
H19A H -0.1388 0.2469 0.5085 0.142 Uiso 1 1 calc R . .
B1 B 0.1212(2) 0.1516(2) 0.32396(18) 0.0521(6) Uani 1 1 d . . .
C21 C -0.1428(3) 0.2833(4) 0.2672(2) 0.1372(17) Uani 1 1 d . . .
H21B H -0.1293 0.3463 0.2212 0.206 Uiso 1 1 calc R . .
H21C H -0.2079 0.3053 0.3032 0.206 Uiso 1 1 calc R . .
H21A H -0.1570 0.2059 0.2359 0.206 Uiso 1 1 calc R . .
C22 C -0.0053(4) 0.3970(3) 0.3762(3) 0.158(2) Uani 1 1 d . . .
H22B H 0.0581 0.3850 0.4195 0.237 Uiso 1 1 calc R . .
H22C H -0.0688 0.4305 0.4090 0.237 Uiso 1 1 calc R . .
H22A H 0.0164 0.4533 0.3276 0.237 Uiso 1 1 calc R . .


_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
O1 B1 1.351(3) . ?
O1 C18 1.462(3) . ?
O2 B1 1.353(3) . ?
O2 C17 1.458(3) . ?
C16 C15 1.399(3) . ?
C16 C9 1.413(3) . ?
C16 B1 1.553(3) . ?
C9 C10 1.426(3) . ?
C9 C8 1.440(3) . ?
C4 C5 1.419(3) . ?
C4 C3 1.420(3) . ?
C4 C10 1.423(3) . ?
C10 C11 1.422(3) . ?
C8 C7 1.346(3) . ?
C8 H8 0.9300 . ?
C11 C14 1.394(3) . ?
C11 C12 1.426(3) . ?
C5 C6 1.394(3) . ?
C5 C7 1.428(3) . ?
C7 H7 0.9300 . ?
C15 C14 1.373(3) . ?
C15 H15 0.9300 . ?
C14 H14 0.9300 . ?
C2 C1 1.374(4) . ?
C2 C3 1.397(3) . ?
C2 H2 0.9300 . ?
C12 C13 1.335(3) . ?
C12 H12 0.9300 . ?
C1 C6 1.377(4) . ?
C1 H1 0.9300 . ?
C3 C13 1.434(4) . ?
C18 C19 1.507(3) . ?
C18 C17 1.529(3) . ?
C18 C20 1.535(4) . ?
C6 H6 0.9300 . ?
C13 H13 0.9300 . ?
C17 C21 1.498(4) . ?
C17 C22 1.550(5) . ?
C20 H20B 0.9600 . ?
C20 H20C 0.9600 . ?
C20 H20A 0.9600 . ?
C19 H19C 0.9600 . ?
C19 H19B 0.9600 . ?
C19 H19A 0.9600 . ?
C21 H21B 0.9600 . ?
C21 H21C 0.9600 . ?
C21 H21A 0.9600 . ?
C22 H22B 0.9600 . ?
C22 H22C 0.9600 . ?
C22 H22A 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
B1 O1 C18 108.66(19) . . ?
B1 O2 C17 109.23(18) . . ?
C15 C16 C9 118.0(2) . . ?
C15 C16 B1 117.1(2) . . ?
C9 C16 B1 124.9(2) . . ?
C16 C9 C10 119.8(2) . . ?
C16 C9 C8 122.91(19) . . ?
C10 C9 C8 117.31(19) . . ?
C5 C4 C3 119.3(2) . . ?
C5 C4 C10 120.6(2) . . ?
C3 C4 C10 120.0(2) . . ?
C11 C10 C4 119.7(2) . . ?
C11 C10 C9 120.1(2) . . ?
C4 C10 C9 120.2(2) . . ?
C7 C8 C9 122.0(2) . . ?
C7 C8 H8 119.0 . . ?
C9 C8 H8 119.0 . . ?
C14 C11 C10 118.7(2) . . ?
C14 C11 C12 122.7(2) . . ?
C10 C11 C12 118.6(2) . . ?
C6 C5 C4 119.5(2) . . ?
C6 C5 C7 122.7(2) . . ?
C4 C5 C7 117.8(2) . . ?
C8 C7 C5 121.9(2) . . ?
C8 C7 H7 119.0 . . ?
C5 C7 H7 119.0 . . ?
C14 C15 C16 122.7(2) . . ?
C14 C15 H15 118.7 . . ?
C16 C15 H15 118.7 . . ?
C15 C14 C11 120.7(2) . . ?
C15 C14 H14 119.7 . . ?
C11 C14 H14 119.7 . . ?
C1 C2 C3 121.0(3) . . ?
C1 C2 H2 119.5 . . ?
C3 C2 H2 119.5 . . ?
C13 C12 C11 121.7(3) . . ?
C13 C12 H12 119.1 . . ?
C11 C12 H12 119.1 . . ?
C2 C1 C6 121.0(3) . . ?
C2 C1 H1 119.5 . . ?
C6 C1 H1 119.5 . . ?
C2 C3 C4 118.9(3) . . ?
C2 C3 C13 122.9(3) . . ?
C4 C3 C13 118.2(2) . . ?
O1 C18 C19 107.4(2) . . ?
O1 C18 C17 103.16(19) . . ?
C19 C18 C17 117.3(2) . . ?
O1 C18 C20 106.5(2) . . ?
C19 C18 C20 109.3(2) . . ?
C17 C18 C20 112.4(2) . . ?
C1 C6 C5 120.4(3) . . ?
C1 C6 H6 119.8 . . ?
C5 C6 H6 119.8 . . ?
C12 C13 C3 121.8(2) . . ?
C12 C13 H13 119.1 . . ?
C3 C13 H13 119.1 . . ?
O2 C17 C21 107.5(2) . . ?
O2 C17 C18 102.4(2) . . ?
C21 C17 C18 116.8(3) . . ?
O2 C17 C22 106.3(3) . . ?
C21 C17 C22 111.8(3) . . ?
C18 C17 C22 111.0(3) . . ?
C18 C20 H20B 109.5 . . ?
C18 C20 H20C 109.5 . . ?
H20B C20 H20C 109.5 . . ?
C18 C20 H20A 109.5 . . ?
H20B C20 H20A 109.5 . . ?
H20C C20 H20A 109.5 . . ?
C18 C19 H19C 109.5 . . ?
C18 C19 H19B 109.5 . . ?
H19C C19 H19B 109.5 . . ?
C18 C19 H19A 109.5 . . ?
H19C C19 H19A 109.5 . . ?
H19B C19 H19A 109.5 . . ?
O1 B1 O2 111.7(2) . . ?
O1 B1 C16 121.3(2) . . ?
O2 B1 C16 126.9(2) . . ?
C17 C21 H21B 109.5 . . ?
C17 C21 H21C 109.5 . . ?
H21B C21 H21C 109.5 . . ?
C17 C21 H21A 109.5 . . ?
H21B C21 H21A 109.5 . . ?
H21C C21 H21A 109.5 . . ?
C17 C22 H22B 109.5 . . ?
C17 C22 H22C 109.5 . . ?
H22B C22 H22C 109.5 . . ?
C17 C22 H22A 109.5 . . ?
H22B C22 H22A 109.5 . . ?
H22C C22 H22A 109.5 . . ?

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
C15 C16 C9 C10 -3.3(3) . . . . ?
B1 C16 C9 C10 175.4(2) . . . . ?
C15 C16 C9 C8 175.9(2) . . . . ?
B1 C16 C9 C8 -5.4(3) . . . . ?
C5 C4 C10 C11 177.2(2) . . . . ?
C3 C4 C10 C11 -0.8(3) . . . . ?
C5 C4 C10 C9 -2.5(3) . . . . ?
C3 C4 C10 C9 179.4(2) . . . . ?
C16 C9 C10 C11 2.2(3) . . . . ?
C8 C9 C10 C11 -177.0(2) . . . . ?
C16 C9 C10 C4 -178.08(19) . . . . ?
C8 C9 C10 C4 2.7(3) . . . . ?
C16 C9 C8 C7 179.9(2) . . . . ?
C10 C9 C8 C7 -0.9(3) . . . . ?
C4 C10 C11 C14 -179.1(2) . . . . ?
C9 C10 C11 C14 0.7(3) . . . . ?
C4 C10 C11 C12 0.6(3) . . . . ?
C9 C10 C11 C12 -179.7(2) . . . . ?
C3 C4 C5 C6 -1.4(3) . . . . ?
C10 C4 C5 C6 -179.5(2) . . . . ?
C3 C4 C5 C7 178.5(2) . . . . ?
C10 C4 C5 C7 0.5(3) . . . . ?
C9 C8 C7 C5 -1.1(4) . . . . ?
C6 C5 C7 C8 -178.7(2) . . . . ?
C4 C5 C7 C8 1.3(3) . . . . ?
C9 C16 C15 C14 1.7(3) . . . . ?
B1 C16 C15 C14 -177.1(2) . . . . ?
C16 C15 C14 C11 1.2(4) . . . . ?
C10 C11 C14 C15 -2.3(3) . . . . ?
C12 C11 C14 C15 178.0(2) . . . . ?
C14 C11 C12 C13 179.8(3) . . . . ?
C10 C11 C12 C13 0.1(4) . . . . ?
C3 C2 C1 C6 -0.7(4) . . . . ?
C1 C2 C3 C4 0.1(4) . . . . ?
C1 C2 C3 C13 178.6(3) . . . . ?
C5 C4 C3 C2 0.9(3) . . . . ?
C10 C4 C3 C2 179.0(2) . . . . ?
C5 C4 C3 C13 -177.7(2) . . . . ?
C10 C4 C3 C13 0.4(3) . . . . ?
B1 O1 C18 C19 -142.4(2) . . . . ?
B1 O1 C18 C17 -17.9(3) . . . . ?
B1 O1 C18 C20 100.6(2) . . . . ?
C2 C1 C6 C5 0.2(4) . . . . ?
C4 C5 C6 C1 0.8(4) . . . . ?
C7 C5 C6 C1 -179.1(2) . . . . ?
C11 C12 C13 C3 -0.5(4) . . . . ?
C2 C3 C13 C12 -178.3(3) . . . . ?
C4 C3 C13 C12 0.3(4) . . . . ?
B1 O2 C17 C21 -142.1(3) . . . . ?
B1 O2 C17 C18 -18.4(3) . . . . ?
B1 O2 C17 C22 98.1(3) . . . . ?
O1 C18 C17 O2 21.3(3) . . . . ?
C19 C18 C17 O2 139.0(2) . . . . ?
C20 C18 C17 O2 -93.0(3) . . . . ?
O1 C18 C17 C21 138.5(3) . . . . ?
C19 C18 C17 C21 -103.8(3) . . . . ?
C20 C18 C17 C21 24.1(4) . . . . ?
O1 C18 C17 C22 -91.8(3) . . . . ?
C19 C18 C17 C22 25.9(3) . . . . ?
C20 C18 C17 C22 153.9(3) . . . . ?
C18 O1 B1 O2 7.0(3) . . . . ?
C18 O1 B1 C16 -174.6(2) . . . . ?
C17 O2 B1 O1 8.0(3) . . . . ?
C17 O2 B1 C16 -170.4(3) . . . . ?
C15 C16 B1 O1 -0.8(3) . . . . ?
C9 C16 B1 O1 -179.5(2) . . . . ?
C15 C16 B1 O2 177.4(2) . . . . ?
C9 C16 B1 O2 -1.3(4) . . . . ?

_diffrn_measured_fraction_theta_max 0.989
_diffrn_reflns_theta_full        26.37
_diffrn_measured_fraction_theta_full 0.989
_refine_diff_density_max         0.273
_refine_diff_density_min         -0.159
_refine_diff_density_rms         0.034


