# 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_BB25m
_database_code_depnum_ccdc_archive 'CCDC 1440306'
_audit_update_record             
;
2015-12-03 deposited with the CCDC.
2016-02-10 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         'C23 H22 O2'
_chemical_formula_sum            'C23 H22 O2'
_chemical_formula_weight         330.40

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

_space_group_crystal_system      monoclinic
_space_group_IT_number           15
_space_group_name_H-M_alt        'C 2/c'
_space_group_name_Hall           '-C 2yc'

_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, -z+1/2'
'x+1/2, y+1/2, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y, z-1/2'
'-x+1/2, -y+1/2, -z'
'x+1/2, -y+1/2, z-1/2'

_cell_length_a                   28.1542(16)
_cell_length_b                   8.5012(5)
_cell_length_c                   17.4613(10)
_cell_angle_alpha                90
_cell_angle_beta                 122.609(1)
_cell_angle_gamma                90
_cell_volume                     3520.5(4)
_cell_formula_units_Z            8
_cell_measurement_temperature    294(2)
_cell_measurement_reflns_used    7804
_cell_measurement_theta_min      2.34
_cell_measurement_theta_max      28.07

_exptl_crystal_description       block
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.247
_exptl_crystal_F_000             1408
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.180
_exptl_crystal_size_mid          0.090
_exptl_crystal_size_min          0.060
_exptl_absorpt_coefficient_mu    0.078
_shelx_estimated_absorpt_T_min   0.986
_shelx_estimated_absorpt_T_max   0.995
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.92
_exptl_absorpt_correction_T_max  0.98
_exptl_absorpt_process_details   'SADABS; Bruker,2001'

_diffrn_ambient_temperature      294(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_measurement_device_type  'Bruker SMART APEX CCD area-detector'
_diffrn_measurement_method       ω
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            19985
_diffrn_reflns_av_unetI/netI     0.0177
_diffrn_reflns_av_R_equivalents  0.0232
_diffrn_reflns_limit_h_min       -36
_diffrn_reflns_limit_h_max       37
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_theta_min         1.717
_diffrn_reflns_theta_max         28.268
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.978
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.978
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.978
_diffrn_reflns_point_group_measured_fraction_full 1.000
_reflns_number_total             4266
_reflns_number_gt                3396
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

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

_computing_data_collection       'SMART (Bruker, 2001)'
_computing_cell_refinement       'SAINT (Bruker, 2001)'
_computing_data_reduction        'SAINT (Bruker, 2001)'
_computing_structure_solution    'SHELXL-2014/7 (Sheldrick, 2015)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2015)'
_computing_molecular_graphics    'SHELXL2014 (Sheldrick, 2015)'
_computing_publication_material  'SHELXL2014 (Sheldrick, 2015)'

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0688P)²+0.8190P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         4266
_refine_ls_number_parameters     226
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0577
_refine_ls_R_factor_gt           0.0471
_refine_ls_wR_factor_ref         0.1348
_refine_ls_wR_factor_gt          0.1251
_refine_ls_goodness_of_fit_ref   1.040
_refine_ls_restrained_S_all      1.040
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 0.21780(4) 0.39707(14) 1.08269(8) 0.0512(3) Uani 1 1 d . . . . .
C2 C 0.20127(5) 0.52673(15) 1.02527(9) 0.0561(3) Uani 1 1 d . . . . .
C3 C 0.22375(6) 0.67261(17) 1.06490(12) 0.0720(4) Uani 1 1 d . . . . .
H3 H 0.2133 0.7609 1.0278 0.086 Uiso 1 1 calc R U . . .
C4 C 0.26083(7) 0.6902(2) 1.15685(14) 0.0855(5) Uani 1 1 d . . . . .
H4 H 0.2748 0.7891 1.1815 0.103 Uiso 1 1 calc R U . . .
C5 C 0.27692(7) 0.5608(2) 1.21165(12) 0.0833(5) Uani 1 1 d . . . . .
H5 H 0.3022 0.5719 1.2740 0.100 Uiso 1 1 calc R U . . .
C6 C 0.25611(5) 0.41394(19) 1.17561(9) 0.0661(4) Uani 1 1 d . . . . .
H6 H 0.2677 0.3263 1.2134 0.079 Uiso 1 1 calc R U . . .
C7 C 0.14983(4) 0.22966(15) 0.96111(8) 0.0516(3) Uani 1 1 d . . . . .
C8 C 0.15668(5) 0.33624(18) 0.89742(9) 0.0636(3) Uani 1 1 d . . . . .
H8A H 0.1902 0.3053 0.8983 0.076 Uiso 1 1 calc R U . . .
H8B H 0.1244 0.3233 0.8358 0.076 Uiso 1 1 calc R U . . .
C9 C 0.16166(5) 0.50744(17) 0.92465(10) 0.0679(4) Uani 1 1 d . . . . .
H9A H 0.1753 0.5683 0.8933 0.081 Uiso 1 1 calc R U . . .
H9B H 0.1248 0.5474 0.9066 0.081 Uiso 1 1 calc R U . . .
C10 C 0.14872(6) 0.05627(17) 0.93959(11) 0.0690(4) Uani 1 1 d . . . . .
H10A H 0.1785 0.0343 0.9289 0.083 Uiso 1 1 calc R U . . .
H10B H 0.1559 -0.0057 0.9915 0.083 Uiso 1 1 calc R U . . .
C11 C 0.09252(6) 0.0082(2) 0.85676(12) 0.0825(5) Uani 1 1 d . . . . .
H11A H 0.0873 0.0612 0.8035 0.099 Uiso 1 1 calc R U . . .
H11B H 0.0926 -0.1042 0.8473 0.099 Uiso 1 1 calc R U . . .
C12 C 0.04367(5) 0.21099(15) 0.87770(8) 0.0540(3) Uani 1 1 d . . . . .
H12 H 0.0401 0.2656 0.8254 0.065 Uiso 1 1 calc R U . . .
C13 C 0.09777(4) 0.26599(14) 0.96424(7) 0.0463(3) Uani 1 1 d . . . . .
H13A H 0.0957 0.3784 0.9714 0.056 Uiso 1 1 calc R U . . .
H13B H 0.1012 0.2141 1.0165 0.056 Uiso 1 1 calc R U . . .
C14 C -0.00826(5) 0.24420(15) 0.88047(8) 0.0544(3) Uani 1 1 d . . . . .
C15 C -0.03260(6) 0.12688(18) 0.90104(11) 0.0735(4) Uani 1 1 d . . . . .
H15 H -0.0170 0.0265 0.9134 0.088 Uiso 1 1 calc R U . . .
C16 C -0.08093(7) 0.1552(2) 0.90380(13) 0.0872(5) Uani 1 1 d . . . . .
H16 H -0.0963 0.0741 0.9194 0.105 Uiso 1 1 calc R U . . .
C17 C -0.10525(6) 0.2989(2) 0.88397(11) 0.0770(4) Uani 1 1 d . . . . .
H17 H -0.1377 0.3150 0.8846 0.092 Uiso 1 1 calc R U . . .
C18 C -0.08196(5) 0.42454(17) 0.86232(8) 0.0585(3) Uani 1 1 d . . . . .
C19 C -0.10668(6) 0.5759(2) 0.84049(10) 0.0702(4) Uani 1 1 d . . . . .
H19 H -0.1399 0.5926 0.8388 0.084 Uiso 1 1 calc R U . . .
C20 C -0.08322(6) 0.6967(2) 0.82208(11) 0.0775(4) Uani 1 1 d . . . . .
H20 H -0.1001 0.7955 0.8085 0.093 Uiso 1 1 calc R U . . .
C21 C -0.03364(6) 0.67331(19) 0.82349(11) 0.0726(4) Uani 1 1 d . . . . .
H21 H -0.0172 0.7571 0.8117 0.087 Uiso 1 1 calc R U . . .
C22 C -0.00925(5) 0.52844(16) 0.84199(9) 0.0586(3) Uani 1 1 d . . . . .
H22 H 0.0234 0.5149 0.8416 0.070 Uiso 1 1 calc R U . . .
C23 C -0.03206(4) 0.39803(15) 0.86171(7) 0.0507(3) Uani 1 1 d . . . . .
O1 O 0.19938(3) 0.24714(10) 1.05261(5) 0.0561(2) Uani 1 1 d . . . . .
O2 O 0.04690(4) 0.04633(12) 0.86689(8) 0.0758(3) Uani 1 1 d . . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C1 O1 1.3696(15) . ?
C1 C6 1.3893(18) . ?
C1 C2 1.3907(17) . ?
C2 C3 1.395(2) . ?
C2 C9 1.498(2) . ?
C3 C4 1.372(2) . ?
C3 H3 0.9300 . ?
C4 C5 1.365(3) . ?
C4 H4 0.9300 . ?
C5 C6 1.379(2) . ?
C5 H5 0.9300 . ?
C6 H6 0.9300 . ?
C7 O1 1.4556(13) . ?
C7 C10 1.5173(19) . ?
C7 C8 1.5252(17) . ?
C7 C13 1.5273(14) . ?
C8 C9 1.514(2) . ?
C8 H8A 0.9700 . ?
C8 H8B 0.9700 . ?
C9 H9A 0.9700 . ?
C9 H9B 0.9700 . ?
C10 C11 1.515(2) . ?
C10 H10A 0.9700 . ?
C10 H10B 0.9700 . ?
C11 O2 1.4254(17) . ?
C11 H11A 0.9700 . ?
C11 H11B 0.9700 . ?
C12 O2 1.4219(15) . ?
C12 C14 1.5151(16) . ?
C12 C13 1.5301(15) . ?
C12 H12 0.9800 . ?
C13 H13A 0.9700 . ?
C13 H13B 0.9700 . ?
C14 C15 1.3634(19) . ?
C14 C23 1.4248(18) . ?
C15 C16 1.408(2) . ?
C15 H15 0.9300 . ?
C16 C17 1.351(2) . ?
C16 H16 0.9300 . ?
C17 C18 1.407(2) . ?
C17 H17 0.9300 . ?
C18 C19 1.414(2) . ?
C18 C23 1.4285(15) . ?
C19 C20 1.350(2) . ?
C19 H19 0.9300 . ?
C20 C21 1.3970(19) . ?
C20 H20 0.9300 . ?
C21 C22 1.3615(19) . ?
C21 H21 0.9300 . ?
C22 C23 1.4137(17) . ?
C22 H22 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
O1 C1 C6 116.05(11) . . ?
O1 C1 C2 123.41(11) . . ?
C6 C1 C2 120.51(13) . . ?
C1 C2 C3 117.45(13) . . ?
C1 C2 C9 120.47(12) . . ?
C3 C2 C9 122.08(12) . . ?
C4 C3 C2 122.20(15) . . ?
C4 C3 H3 118.9 . . ?
C2 C3 H3 118.9 . . ?
C5 C4 C3 119.23(16) . . ?
C5 C4 H4 120.4 . . ?
C3 C4 H4 120.4 . . ?
C4 C5 C6 120.71(16) . . ?
C4 C5 H5 119.6 . . ?
C6 C5 H5 119.6 . . ?
C5 C6 C1 119.87(14) . . ?
C5 C6 H6 120.1 . . ?
C1 C6 H6 120.1 . . ?
O1 C7 C10 104.52(10) . . ?
O1 C7 C8 108.46(10) . . ?
C10 C7 C8 112.97(11) . . ?
O1 C7 C13 108.10(9) . . ?
C10 C7 C13 108.26(10) . . ?
C8 C7 C13 114.01(10) . . ?
C9 C8 C7 111.63(11) . . ?
C9 C8 H8A 109.3 . . ?
C7 C8 H8A 109.3 . . ?
C9 C8 H8B 109.3 . . ?
C7 C8 H8B 109.3 . . ?
H8A C8 H8B 108.0 . . ?
C2 C9 C8 110.97(10) . . ?
C2 C9 H9A 109.4 . . ?
C8 C9 H9A 109.4 . . ?
C2 C9 H9B 109.4 . . ?
C8 C9 H9B 109.4 . . ?
H9A C9 H9B 108.0 . . ?
C11 C10 C7 111.72(11) . . ?
C11 C10 H10A 109.3 . . ?
C7 C10 H10A 109.3 . . ?
C11 C10 H10B 109.3 . . ?
C7 C10 H10B 109.3 . . ?
H10A C10 H10B 107.9 . . ?
O2 C11 C10 111.56(12) . . ?
O2 C11 H11A 109.3 . . ?
C10 C11 H11A 109.3 . . ?
O2 C11 H11B 109.3 . . ?
C10 C11 H11B 109.3 . . ?
H11A C11 H11B 108.0 . . ?
O2 C12 C14 108.62(10) . . ?
O2 C12 C13 109.34(10) . . ?
C14 C12 C13 112.07(9) . . ?
O2 C12 H12 108.9 . . ?
C14 C12 H12 108.9 . . ?
C13 C12 H12 108.9 . . ?
C7 C13 C12 111.50(9) . . ?
C7 C13 H13A 109.3 . . ?
C12 C13 H13A 109.3 . . ?
C7 C13 H13B 109.3 . . ?
C12 C13 H13B 109.3 . . ?
H13A C13 H13B 108.0 . . ?
C15 C14 C23 119.40(12) . . ?
C15 C14 C12 120.18(12) . . ?
C23 C14 C12 120.41(11) . . ?
C14 C15 C16 121.07(15) . . ?
C14 C15 H15 119.5 . . ?
C16 C15 H15 119.5 . . ?
C17 C16 C15 120.77(15) . . ?
C17 C16 H16 119.6 . . ?
C15 C16 H16 119.6 . . ?
C16 C17 C18 120.65(13) . . ?
C16 C17 H17 119.7 . . ?
C18 C17 H17 119.7 . . ?
C17 C18 C19 122.01(12) . . ?
C17 C18 C23 118.99(13) . . ?
C19 C18 C23 119.00(12) . . ?
C20 C19 C18 121.58(12) . . ?
C20 C19 H19 119.2 . . ?
C18 C19 H19 119.2 . . ?
C19 C20 C21 119.97(14) . . ?
C19 C20 H20 120.0 . . ?
C21 C20 H20 120.0 . . ?
C22 C21 C20 120.29(14) . . ?
C22 C21 H21 119.9 . . ?
C20 C21 H21 119.9 . . ?
C21 C22 C23 122.00(12) . . ?
C21 C22 H22 119.0 . . ?
C23 C22 H22 119.0 . . ?
C22 C23 C14 123.82(10) . . ?
C22 C23 C18 117.11(11) . . ?
C14 C23 C18 119.07(11) . . ?
C1 O1 C7 117.18(9) . . ?
C12 O2 C11 111.52(11) . . ?

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 -179.31(10) . . . . ?
C6 C1 C2 C3 -1.18(16) . . . . ?
O1 C1 C2 C9 -0.48(16) . . . . ?
C6 C1 C2 C9 177.66(11) . . . . ?
C1 C2 C3 C4 0.02(18) . . . . ?
C9 C2 C3 C4 -178.80(12) . . . . ?
C2 C3 C4 C5 0.8(2) . . . . ?
C3 C4 C5 C6 -0.4(2) . . . . ?
C4 C5 C6 C1 -0.8(2) . . . . ?
O1 C1 C6 C5 179.85(11) . . . . ?
C2 C1 C6 C5 1.58(18) . . . . ?
O1 C7 C8 C9 -60.70(12) . . . . ?
C10 C7 C8 C9 -176.08(10) . . . . ?
C13 C7 C8 C9 59.78(13) . . . . ?
C1 C2 C9 C8 -14.68(15) . . . . ?
C3 C2 C9 C8 164.10(11) . . . . ?
C7 C8 C9 C2 44.86(13) . . . . ?
O1 C7 C10 C11 166.00(12) . . . . ?
C8 C7 C10 C11 -76.29(15) . . . . ?
C13 C7 C10 C11 50.95(15) . . . . ?
C7 C10 C11 O2 -55.59(19) . . . . ?
O1 C7 C13 C12 -165.58(9) . . . . ?
C10 C7 C13 C12 -52.90(13) . . . . ?
C8 C7 C13 C12 73.74(14) . . . . ?
O2 C12 C13 C7 58.68(13) . . . . ?
C14 C12 C13 C7 179.18(10) . . . . ?
O2 C12 C14 C15 20.22(16) . . . . ?
C13 C12 C14 C15 -100.69(14) . . . . ?
O2 C12 C14 C23 -159.84(11) . . . . ?
C13 C12 C14 C23 79.25(14) . . . . ?
C23 C14 C15 C16 0.2(2) . . . . ?
C12 C14 C15 C16 -179.88(13) . . . . ?
C14 C15 C16 C17 1.6(3) . . . . ?
C15 C16 C17 C18 -1.6(3) . . . . ?
C16 C17 C18 C19 179.43(15) . . . . ?
C16 C17 C18 C23 -0.1(2) . . . . ?
C17 C18 C19 C20 178.27(14) . . . . ?
C23 C18 C19 C20 -2.2(2) . . . . ?
C18 C19 C20 C21 0.6(2) . . . . ?
C19 C20 C21 C22 1.0(2) . . . . ?
C20 C21 C22 C23 -1.0(2) . . . . ?
C21 C22 C23 C14 179.30(13) . . . . ?
C21 C22 C23 C18 -0.55(19) . . . . ?
C15 C14 C23 C22 178.33(12) . . . . ?
C12 C14 C23 C22 -1.61(17) . . . . ?
C15 C14 C23 C18 -1.82(17) . . . . ?
C12 C14 C23 C18 178.23(10) . . . . ?
C17 C18 C23 C22 -178.35(12) . . . . ?
C19 C18 C23 C22 2.11(16) . . . . ?
C17 C18 C23 C14 1.79(17) . . . . ?
C19 C18 C23 C14 -177.75(11) . . . . ?
C6 C1 O1 C7 165.41(10) . . . . ?
C2 C1 O1 C7 -16.38(15) . . . . ?
C10 C7 O1 C1 166.55(10) . . . . ?
C8 C7 O1 C1 45.79(13) . . . . ?
C13 C7 O1 C1 -78.29(12) . . . . ?
C14 C12 O2 C11 175.51(11) . . . . ?
C13 C12 O2 C11 -61.91(14) . . . . ?
C10 C11 O2 C12 61.06(18) . . . . ?

_refine_diff_density_max         0.163
_refine_diff_density_min         -0.220
_refine_diff_density_rms         0.043

