# Electronic Supplementary Material (ESI) for Organic & Biomolecular Chemistry.
# 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_324
_database_code_depnum_ccdc_archive 'CCDC 1472930'
_audit_update_record             
;
2016-04-08 deposited with the CCDC.
2016-04-21 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C23 H32 O3'
_chemical_formula_sum            'C23 H32 O3'
_chemical_formula_weight         356.49

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'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           triclinic
_symmetry_space_group_name_H-M   'P -1'

loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   8.0136(16)
_cell_length_b                   10.278(2)
_cell_length_c                   13.463(3)
_cell_angle_alpha                70.38(3)
_cell_angle_beta                 86.42(3)
_cell_angle_gamma                78.55(3)
_cell_volume                     1023.7(4)
_cell_formula_units_Z            2
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    3850
_cell_measurement_theta_min      4.65
_cell_measurement_theta_max      66.93

_exptl_crystal_description       plate
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.31
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.16
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.157
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             388
_exptl_absorpt_coefficient_mu    0.586
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.6742
_exptl_absorpt_correction_T_max  0.7529
_exptl_absorpt_process_details   SADABS

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      296(2)
_diffrn_radiation_wavelength     1.54178
_diffrn_radiation_type           CuK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         0
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            5726
_diffrn_reflns_av_R_equivalents  0.0163
_diffrn_reflns_av_sigmaI/netI    0.0236
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_theta_min         4.65
_diffrn_reflns_theta_max         65.93
_reflns_number_total             3136
_reflns_number_gt                2942
_reflns_threshold_expression     >2sigma(I)

_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-97 (Sheldrick, 2008)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'


_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)+(0.0657P)²+0.1983P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     SHELXL
_refine_ls_extinction_coef       0.0152(14)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         3136
_refine_ls_number_parameters     236
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0459
_refine_ls_R_factor_gt           0.0441
_refine_ls_wR_factor_ref         0.1250
_refine_ls_wR_factor_gt          0.1229
_refine_ls_goodness_of_fit_ref   1.053
_refine_ls_restrained_S_all      1.053
_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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
O1 O -0.14167(16) 0.59737(13) 0.82304(10) 0.0711(4) Uani 1 1 d . . .
O2 O 0.18886(13) 0.89242(11) 0.58667(8) 0.0547(3) Uani 1 1 d . . .
H2A H 0.2785 0.8749 0.5567 0.082 Uiso 1 1 calc R . .
O3 O 0.48818(15) 0.72540(15) 0.56218(11) 0.0800(4) Uani 1 1 d . . .
C1 C -0.05325(17) 0.68479(15) 0.80730(12) 0.0476(4) Uani 1 1 d . . .
C2 C 0.0309(2) 0.70443(17) 0.89694(12) 0.0547(4) Uani 1 1 d . . .
H2B H 0.0081 0.6337 0.9624 0.066 Uiso 1 1 calc R . .
H2C H -0.0186 0.7960 0.9022 0.066 Uiso 1 1 calc R . .
C3 C 0.22469(19) 0.69354(16) 0.88312(12) 0.0520(4) Uani 1 1 d . . .
C4 C 0.26340(17) 0.78382(14) 0.77072(12) 0.0472(4) Uani 1 1 d . . .
H4A H 0.3849 0.7605 0.7596 0.057 Uiso 1 1 calc R . .
H4B H 0.2381 0.8814 0.7677 0.057 Uiso 1 1 calc R . .
C5 C 0.17143(16) 0.77353(14) 0.67706(11) 0.0420(3) Uani 1 1 d . . .
C6 C 0.24821(17) 0.63642(15) 0.65319(11) 0.0451(3) Uani 1 1 d . . .
H6A H 0.2375 0.5566 0.7168 0.054 Uiso 1 1 calc R . .
C7 C 0.1562(2) 0.61995(19) 0.56252(13) 0.0574(4) Uani 1 1 d . . .
H7A H 0.1662 0.6970 0.4981 0.069 Uiso 1 1 calc R . .
H7B H 0.2081 0.5326 0.5509 0.069 Uiso 1 1 calc R . .
C8 C -0.03026(19) 0.61953(19) 0.59042(14) 0.0578(4) Uani 1 1 d . . .
H8A H -0.0892 0.6109 0.5328 0.069 Uiso 1 1 calc R . .
H8B H -0.0398 0.5392 0.6526 0.069 Uiso 1 1 calc R . .
C9 C -0.11269(18) 0.75382(17) 0.61134(13) 0.0525(4) Uani 1 1 d . . .
H9A H -0.2301 0.7486 0.6317 0.063 Uiso 1 1 calc R . .
H9B H -0.1139 0.8321 0.5462 0.063 Uiso 1 1 calc R . .
C10 C -0.02488(16) 0.78447(14) 0.69724(11) 0.0428(3) Uani 1 1 d . . .
C11 C -0.10566(18) 0.93641(15) 0.69486(13) 0.0508(4) Uani 1 1 d . . .
H11A H -0.0393 0.9623 0.7406 0.061 Uiso 1 1 calc R . .
H11B H -0.0967 1.0003 0.6237 0.061 Uiso 1 1 calc R . .
C12 C -0.29164(19) 0.95779(16) 0.72851(14) 0.0576(4) Uani 1 1 d . . .
H12A H -0.3600 0.9333 0.6829 0.069 Uiso 1 1 calc R . .
H12B H -0.3024 0.8959 0.8001 0.069 Uiso 1 1 calc R . .
C13 C -0.3576(2) 1.10901(18) 0.72290(18) 0.0700(5) Uani 1 1 d . . .
H13A H -0.2839 1.1337 0.7654 0.084 Uiso 1 1 calc R . .
H13B H -0.3493 1.1694 0.6505 0.084 Uiso 1 1 calc R . .
C14 C -0.5379(2) 1.13968(15) 0.75914(14) 0.0564(4) Uani 1 1 d . . .
C15 C -0.5725(3) 1.1390(2) 0.86062(16) 0.0777(5) Uani 1 1 d . . .
H15A H -0.4834 1.1166 0.9081 0.093 Uiso 1 1 calc R . .
C16 C -0.7365(4) 1.1709(3) 0.8927(2) 0.1012(8) Uani 1 1 d . . .
H16A H -0.7574 1.1697 0.9617 0.121 Uiso 1 1 calc R . .
C17 C -0.8695(3) 1.2045(3) 0.8246(3) 0.1008(8) Uani 1 1 d . . .
H17A H -0.9806 1.2272 0.8465 0.121 Uiso 1 1 calc R . .
C18 C -0.8379(3) 1.2044(2) 0.7238(2) 0.0846(6) Uani 1 1 d . . .
H18A H -0.9281 1.2263 0.6772 0.102 Uiso 1 1 calc R . .
C19 C -0.6737(2) 1.17213(18) 0.69077(16) 0.0665(5) Uani 1 1 d . . .
H19A H -0.6537 1.1721 0.6220 0.080 Uiso 1 1 calc R . .
C20 C 0.43571(18) 0.62629(18) 0.62419(13) 0.0546(4) Uani 1 1 d . . .
C21 C 0.5540(2) 0.4897(2) 0.6712(2) 0.0872(7) Uani 1 1 d . . .
H21A H 0.6673 0.4986 0.6458 0.131 Uiso 1 1 calc R . .
H21B H 0.5182 0.4180 0.6514 0.131 Uiso 1 1 calc R . .
H21C H 0.5529 0.4645 0.7466 0.131 Uiso 1 1 calc R . .
C22 C 0.2926(3) 0.7514(2) 0.96063(16) 0.0770(6) Uani 1 1 d . . .
H22A H 0.4134 0.7455 0.9519 0.116 Uiso 1 1 calc R . .
H22B H 0.2686 0.6970 1.0315 0.116 Uiso 1 1 calc R . .
H22C H 0.2382 0.8478 0.9469 0.116 Uiso 1 1 calc R . .
C23 C 0.3083(2) 0.53808(18) 0.91197(14) 0.0644(4) Uani 1 1 d . . .
H23A H 0.4294 0.5299 0.9033 0.097 Uiso 1 1 calc R . .
H23B H 0.2649 0.4975 0.8667 0.097 Uiso 1 1 calc R . .
H23C H 0.2832 0.4893 0.9840 0.097 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 C1 1.2086(18) . ?
O2 C5 1.4287(17) . ?
O2 H2A 0.8200 . ?
O3 C20 1.211(2) . ?
C1 C2 1.507(2) . ?
C1 C10 1.526(2) . ?
C2 C3 1.538(2) . ?
C2 H2B 0.9700 . ?
C2 H2C 0.9700 . ?
C3 C23 1.531(2) . ?
C3 C22 1.535(2) . ?
C3 C4 1.536(2) . ?
C4 C5 1.5431(18) . ?
C4 H4A 0.9700 . ?
C4 H4B 0.9700 . ?
C5 C6 1.550(2) . ?
C5 C10 1.5679(18) . ?
C6 C20 1.5208(19) . ?
C6 C7 1.537(2) . ?
C6 H6A 0.9800 . ?
C7 C8 1.518(2) . ?
C7 H7A 0.9700 . ?
C7 H7B 0.9700 . ?
C8 C9 1.515(2) . ?
C8 H8A 0.9700 . ?
C8 H8B 0.9700 . ?
C9 C10 1.5382(19) . ?
C9 H9A 0.9700 . ?
C9 H9B 0.9700 . ?
C10 C11 1.5577(19) . ?
C11 C12 1.525(2) . ?
C11 H11A 0.9700 . ?
C11 H11B 0.9700 . ?
C12 C13 1.517(2) . ?
C12 H12A 0.9700 . ?
C12 H12B 0.9700 . ?
C13 C14 1.503(2) . ?
C13 H13A 0.9700 . ?
C13 H13B 0.9700 . ?
C14 C15 1.375(3) . ?
C14 C19 1.385(3) . ?
C15 C16 1.368(3) . ?
C15 H15A 0.9300 . ?
C16 C17 1.364(4) . ?
C16 H16A 0.9300 . ?
C17 C18 1.364(4) . ?
C17 H17A 0.9300 . ?
C18 C19 1.376(3) . ?
C18 H18A 0.9300 . ?
C19 H19A 0.9300 . ?
C20 C21 1.490(3) . ?
C21 H21A 0.9600 . ?
C21 H21B 0.9600 . ?
C21 H21C 0.9600 . ?
C22 H22A 0.9600 . ?
C22 H22B 0.9600 . ?
C22 H22C 0.9600 . ?
C23 H23A 0.9600 . ?
C23 H23B 0.9600 . ?
C23 H23C 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
C5 O2 H2A 109.5 . . ?
O1 C1 C2 121.32(15) . . ?
O1 C1 C10 122.53(14) . . ?
C2 C1 C10 116.12(12) . . ?
C1 C2 C3 112.81(12) . . ?
C1 C2 H2B 109.0 . . ?
C3 C2 H2B 109.0 . . ?
C1 C2 H2C 109.0 . . ?
C3 C2 H2C 109.0 . . ?
H2B C2 H2C 107.8 . . ?
C23 C3 C22 107.31(14) . . ?
C23 C3 C4 114.10(13) . . ?
C22 C3 C4 108.03(14) . . ?
C23 C3 C2 108.70(14) . . ?
C22 C3 C2 109.13(14) . . ?
C4 C3 C2 109.45(12) . . ?
C3 C4 C5 118.89(11) . . ?
C3 C4 H4A 107.6 . . ?
C5 C4 H4A 107.6 . . ?
C3 C4 H4B 107.6 . . ?
C5 C4 H4B 107.6 . . ?
H4A C4 H4B 107.0 . . ?
O2 C5 C4 108.28(10) . . ?
O2 C5 C6 109.53(11) . . ?
C4 C5 C6 111.29(11) . . ?
O2 C5 C10 105.64(11) . . ?
C4 C5 C10 111.22(11) . . ?
C6 C5 C10 110.68(10) . . ?
C20 C6 C7 106.92(12) . . ?
C20 C6 C5 112.82(11) . . ?
C7 C6 C5 112.89(12) . . ?
C20 C6 H6A 108.0 . . ?
C7 C6 H6A 108.0 . . ?
C5 C6 H6A 108.0 . . ?
C8 C7 C6 109.31(12) . . ?
C8 C7 H7A 109.8 . . ?
C6 C7 H7A 109.8 . . ?
C8 C7 H7B 109.8 . . ?
C6 C7 H7B 109.8 . . ?
H7A C7 H7B 108.3 . . ?
C9 C8 C7 110.61(12) . . ?
C9 C8 H8A 109.5 . . ?
C7 C8 H8A 109.5 . . ?
C9 C8 H8B 109.5 . . ?
C7 C8 H8B 109.5 . . ?
H8A C8 H8B 108.1 . . ?
C8 C9 C10 114.80(12) . . ?
C8 C9 H9A 108.6 . . ?
C10 C9 H9A 108.6 . . ?
C8 C9 H9B 108.6 . . ?
C10 C9 H9B 108.6 . . ?
H9A C9 H9B 107.5 . . ?
C1 C10 C9 112.05(11) . . ?
C1 C10 C11 107.39(12) . . ?
C9 C10 C11 107.79(12) . . ?
C1 C10 C5 108.85(11) . . ?
C9 C10 C5 111.13(12) . . ?
C11 C10 C5 109.53(11) . . ?
C12 C11 C10 115.50(12) . . ?
C12 C11 H11A 108.4 . . ?
C10 C11 H11A 108.4 . . ?
C12 C11 H11B 108.4 . . ?
C10 C11 H11B 108.4 . . ?
H11A C11 H11B 107.5 . . ?
C13 C12 C11 111.16(13) . . ?
C13 C12 H12A 109.4 . . ?
C11 C12 H12A 109.4 . . ?
C13 C12 H12B 109.4 . . ?
C11 C12 H12B 109.4 . . ?
H12A C12 H12B 108.0 . . ?
C14 C13 C12 115.32(14) . . ?
C14 C13 H13A 108.4 . . ?
C12 C13 H13A 108.4 . . ?
C14 C13 H13B 108.4 . . ?
C12 C13 H13B 108.4 . . ?
H13A C13 H13B 107.5 . . ?
C15 C14 C19 118.08(17) . . ?
C15 C14 C13 120.91(17) . . ?
C19 C14 C13 120.99(17) . . ?
C16 C15 C14 120.9(2) . . ?
C16 C15 H15A 119.6 . . ?
C14 C15 H15A 119.6 . . ?
C17 C16 C15 120.8(2) . . ?
C17 C16 H16A 119.6 . . ?
C15 C16 H16A 119.6 . . ?
C16 C17 C18 119.3(2) . . ?
C16 C17 H17A 120.4 . . ?
C18 C17 H17A 120.4 . . ?
C17 C18 C19 120.5(2) . . ?
C17 C18 H18A 119.7 . . ?
C19 C18 H18A 119.7 . . ?
C18 C19 C14 120.5(2) . . ?
C18 C19 H19A 119.7 . . ?
C14 C19 H19A 119.7 . . ?
O3 C20 C21 120.20(15) . . ?
O3 C20 C6 121.20(15) . . ?
C21 C20 C6 118.57(15) . . ?
C20 C21 H21A 109.5 . . ?
C20 C21 H21B 109.5 . . ?
H21A C21 H21B 109.5 . . ?
C20 C21 H21C 109.5 . . ?
H21A C21 H21C 109.5 . . ?
H21B C21 H21C 109.5 . . ?
C3 C22 H22A 109.5 . . ?
C3 C22 H22B 109.5 . . ?
H22A C22 H22B 109.5 . . ?
C3 C22 H22C 109.5 . . ?
H22A C22 H22C 109.5 . . ?
H22B C22 H22C 109.5 . . ?
C3 C23 H23A 109.5 . . ?
C3 C23 H23B 109.5 . . ?
H23A C23 H23B 109.5 . . ?
C3 C23 H23C 109.5 . . ?
H23A C23 H23C 109.5 . . ?
H23B C23 H23C 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
O1 C1 C2 C3 125.42(16) . . . . ?
C10 C1 C2 C3 -56.56(17) . . . . ?
C1 C2 C3 C23 -77.68(16) . . . . ?
C1 C2 C3 C22 165.58(14) . . . . ?
C1 C2 C3 C4 47.54(16) . . . . ?
C23 C3 C4 C5 75.80(17) . . . . ?
C22 C3 C4 C5 -164.96(13) . . . . ?
C2 C3 C4 C5 -46.23(17) . . . . ?
C3 C4 C5 O2 163.57(12) . . . . ?
C3 C4 C5 C6 -75.99(15) . . . . ?
C3 C4 C5 C10 47.92(16) . . . . ?
O2 C5 C6 C20 59.23(15) . . . . ?
C4 C5 C6 C20 -60.47(16) . . . . ?
C10 C5 C6 C20 175.31(11) . . . . ?
O2 C5 C6 C7 -62.13(14) . . . . ?
C4 C5 C6 C7 178.17(12) . . . . ?
C10 C5 C6 C7 53.95(15) . . . . ?
C20 C6 C7 C8 176.29(13) . . . . ?
C5 C6 C7 C8 -59.07(17) . . . . ?
C6 C7 C8 C9 58.15(18) . . . . ?
C7 C8 C9 C10 -55.97(18) . . . . ?
O1 C1 C10 C9 -3.21(19) . . . . ?
C2 C1 C10 C9 178.80(12) . . . . ?
O1 C1 C10 C11 114.97(15) . . . . ?
C2 C1 C10 C11 -63.02(14) . . . . ?
O1 C1 C10 C5 -126.54(15) . . . . ?
C2 C1 C10 C5 55.47(15) . . . . ?
C8 C9 C10 C1 -71.61(16) . . . . ?
C8 C9 C10 C11 170.45(12) . . . . ?
C8 C9 C10 C5 50.42(17) . . . . ?
O2 C5 C10 C1 -165.53(11) . . . . ?
C4 C5 C10 C1 -48.27(14) . . . . ?
C6 C5 C10 C1 75.99(14) . . . . ?
O2 C5 C10 C9 70.60(13) . . . . ?
C4 C5 C10 C9 -172.14(11) . . . . ?
C6 C5 C10 C9 -47.88(15) . . . . ?
O2 C5 C10 C11 -48.39(14) . . . . ?
C4 C5 C10 C11 68.88(14) . . . . ?
C6 C5 C10 C11 -166.86(11) . . . . ?
C1 C10 C11 C12 -53.70(16) . . . . ?
C9 C10 C11 C12 67.21(17) . . . . ?
C5 C10 C11 C12 -171.76(12) . . . . ?
C10 C11 C12 C13 -179.78(14) . . . . ?
C11 C12 C13 C14 -177.42(15) . . . . ?
C12 C13 C14 C15 95.7(2) . . . . ?
C12 C13 C14 C19 -85.6(2) . . . . ?
C19 C14 C15 C16 -0.6(3) . . . . ?
C13 C14 C15 C16 178.10(19) . . . . ?
C14 C15 C16 C17 -0.2(4) . . . . ?
C15 C16 C17 C18 0.8(4) . . . . ?
C16 C17 C18 C19 -0.6(4) . . . . ?
C17 C18 C19 C14 -0.2(3) . . . . ?
C15 C14 C19 C18 0.8(3) . . . . ?
C13 C14 C19 C18 -177.93(16) . . . . ?
C7 C6 C20 O3 79.01(18) . . . . ?
C5 C6 C20 O3 -45.7(2) . . . . ?
C7 C6 C20 C21 -99.04(19) . . . . ?
C5 C6 C20 C21 136.27(17) . . . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
O2 H2A O3 0.82 2.03 2.7304(19) 143.7 .

_diffrn_measured_fraction_theta_max 0.880
_diffrn_reflns_theta_full        65.93
_diffrn_measured_fraction_theta_full 0.880
_refine_diff_density_max         0.178
_refine_diff_density_min         -0.174
_refine_diff_density_rms         0.033
####################################################################### 
# 
# 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_343
_database_code_depnum_ccdc_archive 'CCDC 1472931'
_audit_update_record             
;
2016-04-08 deposited with the CCDC.
2016-04-21 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C15 H21 B O3'
_chemical_formula_sum            'C15 H21 B O3'
_chemical_formula_weight         260.13

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'
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'

_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                   10.555(2)
_cell_length_b                   7.2517(15)
_cell_length_c                   18.652(4)
_cell_angle_alpha                90.00
_cell_angle_beta                 101.90(3)
_cell_angle_gamma                90.00
_cell_volume                     1397.0(5)
_cell_formula_units_Z            4
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    4919
_cell_measurement_theta_min      2.41
_cell_measurement_theta_max      66.85

_exptl_crystal_description       column
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.32
_exptl_crystal_size_mid          0.21
_exptl_crystal_size_min          0.15
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.237
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             560
_exptl_absorpt_coefficient_mu    0.663
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.6526
_exptl_absorpt_correction_T_max  0.7529
_exptl_absorpt_process_details   SADABS

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      296(2)
_diffrn_radiation_wavelength     1.54178
_diffrn_radiation_type           CuK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         0
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            6044
_diffrn_reflns_av_R_equivalents  0.0213
_diffrn_reflns_av_sigmaI/netI    0.0255
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_theta_min         4.85
_diffrn_reflns_theta_max         67.57
_reflns_number_total             2375
_reflns_number_gt                2307
_reflns_threshold_expression     >2sigma(I)

_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-97 (Sheldrick, 2008)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'

_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)+(0.0560P)²+0.3390P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     SHELXL
_refine_ls_extinction_coef       0.0100(8)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         2375
_refine_ls_number_parameters     173
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0405
_refine_ls_R_factor_gt           0.0398
_refine_ls_wR_factor_ref         0.1061
_refine_ls_wR_factor_gt          0.1055
_refine_ls_goodness_of_fit_ref   1.052
_refine_ls_restrained_S_all      1.052
_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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
O1 O 0.80373(10) 0.70248(15) 0.49460(5) 0.0516(3) Uani 1 1 d . . .
O2 O 0.74271(9) 0.58202(12) 0.23746(4) 0.0373(3) Uani 1 1 d . . .
O3 O 0.74823(11) 0.60501(15) 0.11302(5) 0.0543(3) Uani 1 1 d . . .
H3A H 0.7638 0.6807 0.0834 0.081 Uiso 1 1 calc R . .
B1 B 0.75032(14) 0.6888(2) 0.17759(8) 0.0386(3) Uani 1 1 d . . .
C1 C 0.73265(13) 0.68225(18) 0.43554(7) 0.0381(3) Uani 1 1 d . . .
C2 C 0.59152(14) 0.7258(2) 0.42529(8) 0.0518(4) Uani 1 1 d . . .
H2A H 0.5770 0.7992 0.4663 0.062 Uiso 1 1 calc R . .
H2B H 0.5431 0.6119 0.4246 0.062 Uiso 1 1 calc R . .
C3 C 0.54269(13) 0.8303(2) 0.35473(8) 0.0478(4) Uani 1 1 d . . .
H3B H 0.5802 0.9529 0.3585 0.057 Uiso 1 1 calc R . .
H3C H 0.4493 0.8429 0.3466 0.057 Uiso 1 1 calc R . .
C4 C 0.57902(12) 0.72879(19) 0.29042(7) 0.0390(3) Uani 1 1 d . . .
H4A H 0.5465 0.7979 0.2459 0.047 Uiso 1 1 calc R . .
H4B H 0.5367 0.6094 0.2854 0.047 Uiso 1 1 calc R . .
C5 C 0.72471(11) 0.70028(16) 0.29816(6) 0.0317(3) Uani 1 1 d . . .
C6 C 0.79017(12) 0.88548(17) 0.28393(6) 0.0358(3) Uani 1 1 d . . .
H6A H 0.7510 0.9892 0.3051 0.043 Uiso 1 1 calc R . .
C7 C 0.93732(13) 0.8878(2) 0.30914(8) 0.0471(4) Uani 1 1 d . . .
H7A H 0.9757 0.8182 0.2746 0.057 Uiso 1 1 calc R . .
H7B H 0.9679 1.0139 0.3092 0.057 Uiso 1 1 calc R . .
C8 C 0.98156(13) 0.8071(2) 0.38461(8) 0.0488(4) Uani 1 1 d . . .
H8A H 0.9489 0.8813 0.4201 0.059 Uiso 1 1 calc R . .
H8B H 1.0754 0.8078 0.3977 0.059 Uiso 1 1 calc R . .
C9 C 0.93227(12) 0.6110(2) 0.38602(7) 0.0428(3) Uani 1 1 d . . .
H9A H 0.9669 0.5573 0.4337 0.051 Uiso 1 1 calc R . .
H9B H 0.9637 0.5387 0.3496 0.051 Uiso 1 1 calc R . .
C10 C 0.78447(12) 0.60057(17) 0.37083(6) 0.0336(3) Uani 1 1 d . . .
C11 C 0.74065(15) 0.39395(18) 0.36593(7) 0.0433(3) Uani 1 1 d . . .
H11A H 0.6477 0.3897 0.3477 0.052 Uiso 1 1 calc R . .
H11B H 0.7810 0.3321 0.3303 0.052 Uiso 1 1 calc R . .
C12 C 0.77190(17) 0.2889(2) 0.43603(8) 0.0539(4) Uani 1 1 d . . .
H12A H 0.8588 0.2740 0.4579 0.065 Uiso 1 1 calc R . .
C13 C 0.6859(2) 0.2161(2) 0.46915(9) 0.0690(5) Uani 1 1 d . . .
H13A H 0.5981 0.2282 0.4489 0.083 Uiso 1 1 calc R . .
H13B H 0.7127 0.1523 0.5129 0.083 Uiso 1 1 calc R . .
C14 C 0.76024(12) 0.89669(18) 0.20107(7) 0.0385(3) Uani 1 1 d . . .
C15 C 0.74861(14) 1.0490(2) 0.16146(8) 0.0512(4) Uani 1 1 d . . .
H15C H 0.7591 1.1635 0.1844 0.061 Uiso 1 1 calc R . .
H15A H 0.7300 1.0419 0.1106 0.061 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 C1 1.2071(16) . ?
O2 B1 1.3747(17) . ?
O2 C5 1.4636(14) . ?
O3 B1 1.3449(18) . ?
O3 H3A 0.8200 . ?
B1 C14 1.568(2) . ?
C1 C2 1.496(2) . ?
C1 C10 1.5424(17) . ?
C2 C3 1.514(2) . ?
C2 H2A 0.9700 . ?
C2 H2B 0.9700 . ?
C3 C4 1.5224(19) . ?
C3 H3B 0.9700 . ?
C3 H3C 0.9700 . ?
C4 C5 1.5286(17) . ?
C4 H4A 0.9700 . ?
C4 H4B 0.9700 . ?
C5 C10 1.5510(16) . ?
C5 C6 1.5579(17) . ?
C6 C14 1.5146(17) . ?
C6 C7 1.5272(18) . ?
C6 H6A 0.9800 . ?
C7 C8 1.507(2) . ?
C7 H7A 0.9700 . ?
C7 H7B 0.9700 . ?
C8 C9 1.516(2) . ?
C8 H8A 0.9700 . ?
C8 H8B 0.9700 . ?
C9 C10 1.5289(17) . ?
C9 H9A 0.9700 . ?
C9 H9B 0.9700 . ?
C10 C11 1.5651(18) . ?
C11 C12 1.4901(19) . ?
C11 H11A 0.9700 . ?
C11 H11B 0.9700 . ?
C12 C13 1.310(3) . ?
C12 H12A 0.9300 . ?
C13 H13A 0.9300 . ?
C13 H13B 0.9300 . ?
C14 C15 1.321(2) . ?
C15 H15C 0.9300 . ?
C15 H15A 0.9300 . ?

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 C5 109.70(10) . . ?
B1 O3 H3A 109.5 . . ?
O3 B1 O2 118.71(13) . . ?
O3 B1 C14 132.25(12) . . ?
O2 B1 C14 109.05(11) . . ?
O1 C1 C2 120.40(12) . . ?
O1 C1 C10 120.45(12) . . ?
C2 C1 C10 119.05(11) . . ?
C1 C2 C3 111.60(11) . . ?
C1 C2 H2A 109.3 . . ?
C3 C2 H2A 109.3 . . ?
C1 C2 H2B 109.3 . . ?
C3 C2 H2B 109.3 . . ?
H2A C2 H2B 108.0 . . ?
C2 C3 C4 110.31(12) . . ?
C2 C3 H3B 109.6 . . ?
C4 C3 H3B 109.6 . . ?
C2 C3 H3C 109.6 . . ?
C4 C3 H3C 109.6 . . ?
H3B C3 H3C 108.1 . . ?
C3 C4 C5 113.76(11) . . ?
C3 C4 H4A 108.8 . . ?
C5 C4 H4A 108.8 . . ?
C3 C4 H4B 108.8 . . ?
C5 C4 H4B 108.8 . . ?
H4A C4 H4B 107.7 . . ?
O2 C5 C4 107.14(9) . . ?
O2 C5 C10 107.97(9) . . ?
C4 C5 C10 111.44(10) . . ?
O2 C5 C6 103.91(9) . . ?
C4 C5 C6 109.89(10) . . ?
C10 C5 C6 115.85(10) . . ?
C14 C6 C7 107.37(11) . . ?
C14 C6 C5 102.33(10) . . ?
C7 C6 C5 114.56(11) . . ?
C14 C6 H6A 110.7 . . ?
C7 C6 H6A 110.7 . . ?
C5 C6 H6A 110.7 . . ?
C8 C7 C6 112.51(11) . . ?
C8 C7 H7A 109.1 . . ?
C6 C7 H7A 109.1 . . ?
C8 C7 H7B 109.1 . . ?
C6 C7 H7B 109.1 . . ?
H7A C7 H7B 107.8 . . ?
C7 C8 C9 109.81(11) . . ?
C7 C8 H8A 109.7 . . ?
C9 C8 H8A 109.7 . . ?
C7 C8 H8B 109.7 . . ?
C9 C8 H8B 109.7 . . ?
H8A C8 H8B 108.2 . . ?
C8 C9 C10 112.59(11) . . ?
C8 C9 H9A 109.1 . . ?
C10 C9 H9A 109.1 . . ?
C8 C9 H9B 109.1 . . ?
C10 C9 H9B 109.1 . . ?
H9A C9 H9B 107.8 . . ?
C9 C10 C1 110.42(10) . . ?
C9 C10 C5 110.75(10) . . ?
C1 C10 C5 111.03(10) . . ?
C9 C10 C11 109.65(11) . . ?
C1 C10 C11 105.38(10) . . ?
C5 C10 C11 109.47(10) . . ?
C12 C11 C10 115.38(11) . . ?
C12 C11 H11A 108.4 . . ?
C10 C11 H11A 108.4 . . ?
C12 C11 H11B 108.4 . . ?
C10 C11 H11B 108.4 . . ?
H11A C11 H11B 107.5 . . ?
C13 C12 C11 124.78(17) . . ?
C13 C12 H12A 117.6 . . ?
C11 C12 H12A 117.6 . . ?
C12 C13 H13A 120.0 . . ?
C12 C13 H13B 120.0 . . ?
H13A C13 H13B 120.0 . . ?
C15 C14 C6 126.27(13) . . ?
C15 C14 B1 130.94(12) . . ?
C6 C14 B1 102.78(10) . . ?
C14 C15 H15C 120.0 . . ?
C14 C15 H15A 120.0 . . ?
H15C C15 H15A 120.0 . . ?

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 O2 B1 O3 -170.57(12) . . . . ?
C5 O2 B1 C14 9.42(14) . . . . ?
O1 C1 C2 C3 136.56(14) . . . . ?
C10 C1 C2 C3 -46.96(17) . . . . ?
C1 C2 C3 C4 52.14(16) . . . . ?
C2 C3 C4 C5 -58.77(15) . . . . ?
B1 O2 C5 C4 88.34(12) . . . . ?
B1 O2 C5 C10 -151.52(10) . . . . ?
B1 O2 C5 C6 -27.97(12) . . . . ?
C3 C4 C5 O2 173.01(10) . . . . ?
C3 C4 C5 C10 55.11(14) . . . . ?
C3 C4 C5 C6 -74.71(13) . . . . ?
O2 C5 C6 C14 35.06(11) . . . . ?
C4 C5 C6 C14 -79.31(11) . . . . ?
C10 C5 C6 C14 153.30(10) . . . . ?
O2 C5 C6 C7 -80.79(12) . . . . ?
C4 C5 C6 C7 164.85(10) . . . . ?
C10 C5 C6 C7 37.46(14) . . . . ?
C14 C6 C7 C8 -158.28(12) . . . . ?
C5 C6 C7 C8 -45.38(16) . . . . ?
C6 C7 C8 C9 57.61(16) . . . . ?
C7 C8 C9 C10 -63.19(15) . . . . ?
C8 C9 C10 C1 -69.55(13) . . . . ?
C8 C9 C10 C5 53.86(14) . . . . ?
C8 C9 C10 C11 174.77(11) . . . . ?
O1 C1 C10 C9 -17.52(16) . . . . ?
C2 C1 C10 C9 165.99(12) . . . . ?
O1 C1 C10 C5 -140.77(12) . . . . ?
C2 C1 C10 C5 42.75(16) . . . . ?
O1 C1 C10 C11 100.81(14) . . . . ?
C2 C1 C10 C11 -75.67(14) . . . . ?
O2 C5 C10 C9 75.20(12) . . . . ?
C4 C5 C10 C9 -167.40(10) . . . . ?
C6 C5 C10 C9 -40.78(14) . . . . ?
O2 C5 C10 C1 -161.75(9) . . . . ?
C4 C5 C10 C1 -44.34(13) . . . . ?
C6 C5 C10 C1 82.27(13) . . . . ?
O2 C5 C10 C11 -45.82(13) . . . . ?
C4 C5 C10 C11 71.58(13) . . . . ?
C6 C5 C10 C11 -161.80(10) . . . . ?
C9 C10 C11 C12 68.33(16) . . . . ?
C1 C10 C11 C12 -50.51(16) . . . . ?
C5 C10 C11 C12 -169.98(12) . . . . ?
C10 C11 C12 C13 117.19(17) . . . . ?
C7 C6 C14 C15 -86.85(16) . . . . ?
C5 C6 C14 C15 152.21(14) . . . . ?
C7 C6 C14 B1 92.19(12) . . . . ?
C5 C6 C14 B1 -28.75(12) . . . . ?
O3 B1 C14 C15 12.4(3) . . . . ?
O2 B1 C14 C15 -167.60(14) . . . . ?
O3 B1 C14 C6 -166.60(15) . . . . ?
O2 B1 C14 C6 13.42(14) . . . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
O3 H3A O1 0.82 1.98 2.7758(14) 163.2 4_575

_diffrn_measured_fraction_theta_max 0.942
_diffrn_reflns_theta_full        67.57
_diffrn_measured_fraction_theta_full 0.942
_refine_diff_density_max         0.184
_refine_diff_density_min         -0.171
_refine_diff_density_rms         0.042
