# Electronic Supplementary Material (ESI) for ChemComm.
# This journal is © The Royal Society of Chemistry 2014

#######################################################################
#
#                 Cambridge Crystallographic Data Centre
#                                CCDC 
# 
#######################################################################
# 
#  This CIF contains data from an original supplementary publication
#  deposited with the CCDC, and may include chemical, crystal,
#  experimental, refinement, atomic coordinates,
#  anisotropic displacement parameters and molecular geometry data,
#  as required by the journal to which it was submitted.
#
#  This CIF is provided on the understanding that it is used for bona
#  fide research purposes only. It may contain copyright material
#  of the CCDC or of third parties, and may not be copied or further
#  disseminated in any form, whether machine-readable or not,
#  except for the purpose of generating routine backup copies
#  on your local computer system.
# 
#  For further information on the CCDC, data deposition and
#  data retrieval see:
#                         www.ccdc.cam.ac.uk
#
#  Bona fide researchers may freely download Mercury and enCIFer
#  from this site to visualise CIF-encoded structures and 
#  to carry out CIF format checking respectively.
#
data_z

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C19 H21 B O3'
_chemical_formula_weight         308.17

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 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           ?
_symmetry_space_group_name_H-M   ?

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                   11.2927(10)
_cell_length_b                   10.9965(10)
_cell_length_c                   13.6864(13)
_cell_angle_alpha                90.00
_cell_angle_beta                 107.263(3)
_cell_angle_gamma                90.00
_cell_volume                     1623.0(3)
_cell_formula_units_Z            4
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    ?
_cell_measurement_theta_min      ?
_cell_measurement_theta_max      ?

_exptl_crystal_description       ?
_exptl_crystal_colour            ?
_exptl_crystal_size_max          0.46
_exptl_crystal_size_mid          0.32
_exptl_crystal_size_min          0.26
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.261
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             656
_exptl_absorpt_coefficient_mu    0.083
_exptl_absorpt_correction_type   ?
_exptl_absorpt_correction_T_min  0.9629
_exptl_absorpt_correction_T_max  0.9788
_exptl_absorpt_process_details   ?

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      296(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  ?
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            18296
_diffrn_reflns_av_R_equivalents  0.0373
_diffrn_reflns_av_sigmaI/netI    0.0250
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_theta_min         2.42
_diffrn_reflns_theta_max         25.01
_reflns_number_total             2843
_reflns_number_gt                1969
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_molecular_graphics    ?
_computing_publication_material  ?

_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)+(0.1889P)²+4.3334P] 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         2843
_refine_ls_number_parameters     208
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1693
_refine_ls_R_factor_gt           0.1364
_refine_ls_wR_factor_ref         0.3979
_refine_ls_wR_factor_gt          0.3608
_refine_ls_goodness_of_fit_ref   1.093
_refine_ls_restrained_S_all      1.093
_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 0.8917(5) 0.8299(4) 0.2502(3) 0.0858(16) Uani 1 1 d . . .
O2 O 0.9049(4) 0.8726(4) 0.0914(3) 0.0657(12) Uani 1 1 d . . .
O3 O 0.8689(6) 0.6782(5) 0.0300(4) 0.0887(16) Uani 1 1 d . . .
B1 B 0.9385(7) 0.9041(6) 0.1914(5) 0.0623(17) Uani 1 1 d . . .
C1 C 1.1404(5) 1.1408(5) 0.3791(4) 0.0549(14) Uani 1 1 d . . .
C2 C 1.1859(7) 1.1621(7) 0.4855(5) 0.0778(19) Uani 1 1 d . . .
H2A H 1.1738 1.1054 0.5321 0.093 Uiso 1 1 calc R . .
C3 C 1.2476(7) 1.2673(8) 0.5180(6) 0.086(2) Uani 1 1 d . . .
H3A H 1.2763 1.2831 0.5878 0.103 Uiso 1 1 calc R . .
C4 C 1.2698(6) 1.3539(6) 0.4489(6) 0.078(2) Uani 1 1 d . . .
H4A H 1.3127 1.4249 0.4743 0.094 Uiso 1 1 calc R . .
C5 C 1.2307(5) 1.3355(6) 0.3487(6) 0.0720(19) Uani 1 1 d . . .
H5A H 1.2461 1.3928 0.3041 0.086 Uiso 1 1 calc R . .
C6 C 1.1632(5) 1.2242(5) 0.3095(4) 0.0563(14) Uani 1 1 d . . .
C7 C 1.1220(5) 1.2018(5) 0.2035(5) 0.0589(15) Uani 1 1 d . . .
H7A H 1.1400 1.2569 0.1584 0.071 Uiso 1 1 calc R . .
C8 C 1.0564(5) 1.1006(5) 0.1674(4) 0.0544(14) Uani 1 1 d . . .
H8A H 1.0310 1.0860 0.0973 0.065 Uiso 1 1 calc R . .
C9 C 1.0251(5) 1.0157(5) 0.2341(4) 0.0555(14) Uani 1 1 d . . .
C10 C 1.0686(5) 1.0347(5) 0.3370(4) 0.0592(15) Uani 1 1 d . . .
H10A H 1.0515 0.9777 0.3812 0.071 Uiso 1 1 calc R . .
C11 C 0.8262(7) 0.7679(5) 0.0755(5) 0.075(2) Uani 1 1 d . . .
C12 C 0.6973(8) 0.8057(9) 0.0073(6) 0.115(4) Uani 1 1 d . . .
H12A H 0.6544 0.7362 -0.0310 0.138 Uiso 1 1 calc R . .
H12B H 0.7047 0.8678 -0.0408 0.138 Uiso 1 1 calc R . .
C13 C 0.6247(8) 0.8555(9) 0.0785(8) 0.110(3) Uani 1 1 d . . .
H13A H 0.6430 0.9410 0.0929 0.132 Uiso 1 1 calc R . .
H13B H 0.5361 0.8465 0.0468 0.132 Uiso 1 1 calc R . .
C14 C 0.6665(6) 0.7816(6) 0.1756(7) 0.081(2) Uani 1 1 d . . .
H14A H 0.6150 0.7100 0.1712 0.097 Uiso 1 1 calc R . .
H14B H 0.6636 0.8295 0.2343 0.097 Uiso 1 1 calc R . .
C15 C 0.8097(8) 0.7435(7) 0.1835(5) 0.088(2) Uani 1 1 d . . .
C16 C 0.8322(10) 0.6252(8) 0.2272(6) 0.103(3) Uani 1 1 d . . .
H16A H 0.7746 0.5683 0.1836 0.123 Uiso 1 1 calc R . .
H16B H 0.8173 0.6257 0.2934 0.123 Uiso 1 1 calc R . .
C17 C 0.9686(6) 0.5811(6) 0.2407(6) 0.0751(19) Uani 1 1 d . . .
H17A H 1.0237 0.6432 0.2796 0.090 Uiso 1 1 calc R . .
H17B H 0.9817 0.5088 0.2832 0.090 Uiso 1 1 calc R . .
C18 C 1.0102(8) 0.5531(8) 0.1535(6) 0.098(3) Uani 1 1 d . . .
H18A H 1.0987 0.5377 0.1778 0.117 Uiso 1 1 calc R . .
H18B H 0.9705 0.4781 0.1236 0.117 Uiso 1 1 calc R . .
C19 C 0.9882(7) 0.6424(6) 0.0742(6) 0.0741(19) Uani 1 1 d . . .
H19B H 1.0367 0.7140 0.1021 0.089 Uiso 1 1 calc R . .
H19A H 1.0200 0.6108 0.0207 0.089 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 1.358(8) . ?
O1 C15 1.446(8) . ?
O2 B1 1.352(8) . ?
O2 C11 1.432(7) . ?
O3 C11 1.330(8) . ?
O3 C19 1.361(9) . ?
B1 C9 1.570(9) . ?
C1 C6 1.400(8) . ?
C1 C2 1.413(8) . ?
C1 C10 1.440(8) . ?
C2 C3 1.356(10) . ?
C2 H2A 0.9300 . ?
C3 C4 1.415(11) . ?
C3 H3A 0.9300 . ?
C4 C5 1.325(10) . ?
C4 H4A 0.9300 . ?
C5 C6 1.457(8) . ?
C5 H5A 0.9300 . ?
C6 C7 1.408(8) . ?
C7 C8 1.347(8) . ?
C7 H7A 0.9300 . ?
C8 C9 1.423(8) . ?
C8 H8A 0.9300 . ?
C9 C10 1.363(8) . ?
C10 H10A 0.9300 . ?
C11 C12 1.535(12) . ?
C11 C15 1.568(9) . ?
C12 C13 1.548(14) . ?
C12 H12A 0.9700 . ?
C12 H12B 0.9700 . ?
C13 C14 1.509(13) . ?
C13 H13A 0.9700 . ?
C13 H13B 0.9700 . ?
C14 C15 1.643(11) . ?
C14 H14A 0.9700 . ?
C14 H14B 0.9700 . ?
C15 C16 1.423(11) . ?
C16 C17 1.573(12) . ?
C16 H16A 0.9700 . ?
C16 H16B 0.9700 . ?
C17 C18 1.439(10) . ?
C17 H17A 0.9700 . ?
C17 H17B 0.9700 . ?
C18 C19 1.430(11) . ?
C18 H18A 0.9700 . ?
C18 H18B 0.9700 . ?
C19 H19B 0.9700 . ?
C19 H19A 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 O1 C15 108.0(5) . . ?
B1 O2 C11 109.6(5) . . ?
C11 O3 C19 117.1(6) . . ?
O2 B1 O1 113.9(5) . . ?
O2 B1 C9 122.3(5) . . ?
O1 B1 C9 123.9(6) . . ?
C6 C1 C2 120.6(6) . . ?
C6 C1 C10 117.0(5) . . ?
C2 C1 C10 122.4(6) . . ?
C3 C2 C1 118.2(7) . . ?
C3 C2 H2A 120.9 . . ?
C1 C2 H2A 120.9 . . ?
C2 C3 C4 122.1(7) . . ?
C2 C3 H3A 119.0 . . ?
C4 C3 H3A 119.0 . . ?
C5 C4 C3 121.2(6) . . ?
C5 C4 H4A 119.4 . . ?
C3 C4 H4A 119.4 . . ?
C4 C5 C6 119.1(7) . . ?
C4 C5 H5A 120.4 . . ?
C6 C5 H5A 120.4 . . ?
C1 C6 C7 121.0(5) . . ?
C1 C6 C5 118.8(5) . . ?
C7 C6 C5 120.2(6) . . ?
C8 C7 C6 120.0(5) . . ?
C8 C7 H7A 120.0 . . ?
C6 C7 H7A 120.0 . . ?
C7 C8 C9 121.4(5) . . ?
C7 C8 H8A 119.3 . . ?
C9 C8 H8A 119.3 . . ?
C10 C9 C8 118.7(5) . . ?
C10 C9 B1 119.9(5) . . ?
C8 C9 B1 121.3(5) . . ?
C9 C10 C1 121.7(5) . . ?
C9 C10 H10A 119.2 . . ?
C1 C10 H10A 119.2 . . ?
O3 C11 O2 111.9(6) . . ?
O3 C11 C12 109.1(7) . . ?
O2 C11 C12 108.0(5) . . ?
O3 C11 C15 118.4(6) . . ?
O2 C11 C15 103.7(5) . . ?
C12 C11 C15 105.2(7) . . ?
C11 C12 C13 107.3(6) . . ?
C11 C12 H12A 110.3 . . ?
C13 C12 H12A 110.3 . . ?
C11 C12 H12B 110.3 . . ?
C13 C12 H12B 110.3 . . ?
H12A C12 H12B 108.5 . . ?
C14 C13 C12 106.1(6) . . ?
C14 C13 H13A 110.5 . . ?
C12 C13 H13A 110.5 . . ?
C14 C13 H13B 110.5 . . ?
C12 C13 H13B 110.5 . . ?
H13A C13 H13B 108.7 . . ?
C13 C14 C15 103.9(6) . . ?
C13 C14 H14A 111.0 . . ?
C15 C14 H14A 111.0 . . ?
C13 C14 H14B 111.0 . . ?
C15 C14 H14B 111.0 . . ?
H14A C14 H14B 109.0 . . ?
C16 C15 O1 109.5(7) . . ?
C16 C15 C11 119.7(7) . . ?
O1 C15 C11 104.5(5) . . ?
C16 C15 C14 108.1(6) . . ?
O1 C15 C14 108.0(6) . . ?
C11 C15 C14 106.5(6) . . ?
C15 C16 C17 112.2(7) . . ?
C15 C16 H16A 109.2 . . ?
C17 C16 H16A 109.2 . . ?
C15 C16 H16B 109.2 . . ?
C17 C16 H16B 109.2 . . ?
H16A C16 H16B 107.9 . . ?
C18 C17 C16 121.2(7) . . ?
C18 C17 H17A 107.0 . . ?
C16 C17 H17A 107.0 . . ?
C18 C17 H17B 107.0 . . ?
C16 C17 H17B 107.0 . . ?
H17A C17 H17B 106.8 . . ?
C19 C18 C17 117.2(6) . . ?
C19 C18 H18A 108.0 . . ?
C17 C18 H18A 108.0 . . ?
C19 C18 H18B 108.0 . . ?
C17 C18 H18B 108.0 . . ?
H18A C18 H18B 107.2 . . ?
O3 C19 C18 117.5(6) . . ?
O3 C19 H19B 107.9 . . ?
C18 C19 H19B 107.9 . . ?
O3 C19 H19A 107.9 . . ?
C18 C19 H19A 107.9 . . ?
H19B C19 H19A 107.2 . . ?

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
C11 O2 B1 O1 0.6(9) . . . . ?
C11 O2 B1 C9 -180.0(6) . . . . ?
C15 O1 B1 O2 -4.7(9) . . . . ?
C15 O1 B1 C9 175.9(7) . . . . ?
C6 C1 C2 C3 2.6(9) . . . . ?
C10 C1 C2 C3 -176.9(6) . . . . ?
C1 C2 C3 C4 -1.5(11) . . . . ?
C2 C3 C4 C5 0.1(11) . . . . ?
C3 C4 C5 C6 0.3(9) . . . . ?
C2 C1 C6 C7 177.7(5) . . . . ?
C10 C1 C6 C7 -2.7(8) . . . . ?
C2 C1 C6 C5 -2.2(8) . . . . ?
C10 C1 C6 C5 177.3(5) . . . . ?
C4 C5 C6 C1 0.8(8) . . . . ?
C4 C5 C6 C7 -179.2(6) . . . . ?
C1 C6 C7 C8 2.0(8) . . . . ?
C5 C6 C7 C8 -178.0(5) . . . . ?
C6 C7 C8 C9 1.2(9) . . . . ?
C7 C8 C9 C10 -3.6(8) . . . . ?
C7 C8 C9 B1 174.4(6) . . . . ?
O2 B1 C9 C10 -171.9(6) . . . . ?
O1 B1 C9 C10 7.4(10) . . . . ?
O2 B1 C9 C8 10.1(10) . . . . ?
O1 B1 C9 C8 -170.5(6) . . . . ?
C8 C9 C10 C1 2.8(8) . . . . ?
B1 C9 C10 C1 -175.2(5) . . . . ?
C6 C1 C10 C9 0.3(8) . . . . ?
C2 C1 C10 C9 179.8(6) . . . . ?
C19 O3 C11 O2 53.4(8) . . . . ?
C19 O3 C11 C12 172.8(6) . . . . ?
C19 O3 C11 C15 -67.0(8) . . . . ?
B1 O2 C11 O3 -125.4(6) . . . . ?
B1 O2 C11 C12 114.6(7) . . . . ?
B1 O2 C11 C15 3.4(8) . . . . ?
O3 C11 C12 C13 151.5(7) . . . . ?
O2 C11 C12 C13 -86.7(7) . . . . ?
C15 C11 C12 C13 23.5(8) . . . . ?
C11 C12 C13 C14 -34.5(9) . . . . ?
C12 C13 C14 C15 29.7(8) . . . . ?
B1 O1 C15 C16 135.7(7) . . . . ?
B1 O1 C15 C11 6.3(8) . . . . ?
B1 O1 C15 C14 -106.8(6) . . . . ?
O3 C11 C15 C16 -4.3(11) . . . . ?
O2 C11 C15 C16 -128.8(7) . . . . ?
C12 C11 C15 C16 117.9(8) . . . . ?
O3 C11 C15 O1 118.8(7) . . . . ?
O2 C11 C15 O1 -5.8(8) . . . . ?
C12 C11 C15 O1 -119.1(7) . . . . ?
O3 C11 C15 C14 -127.1(7) . . . . ?
O2 C11 C15 C14 108.3(6) . . . . ?
C12 C11 C15 C14 -5.0(7) . . . . ?
C13 C14 C15 C16 -145.3(7) . . . . ?
C13 C14 C15 O1 96.3(7) . . . . ?
C13 C14 C15 C11 -15.4(7) . . . . ?
O1 C15 C16 C17 -61.2(8) . . . . ?
C11 C15 C16 C17 59.3(9) . . . . ?
C14 C15 C16 C17 -178.6(6) . . . . ?
C15 C16 C17 C18 -68.8(9) . . . . ?
C16 C17 C18 C19 50.8(11) . . . . ?
C11 O3 C19 C18 86.3(8) . . . . ?
C17 C18 C19 O3 -57.1(10) . . . . ?

_diffrn_measured_fraction_theta_max 0.996
_diffrn_reflns_theta_full        25.01
_diffrn_measured_fraction_theta_full 0.996
_refine_diff_density_max         1.142
_refine_diff_density_min         -0.362
_refine_diff_density_rms         0.091
_database_code_depnum_ccdc_archive 'CCDC 988990'
