# Electronic Supplementary Material (ESI) for Chemical Science.
# This journal is © The Royal Society of Chemistry 2015

####################################################################### 
# 
# 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_cd21401
_database_code_depnum_ccdc_archive 'CCDC 980558'
_audit_update_record             
;
2014-01-08 deposited with the CCDC.
2015-06-23 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C20 H16 Br2 O'
_chemical_formula_weight         432.15

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'
Br Br -0.2901 2.4595 '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                   7.1574(15)
_cell_length_b                   11.250(2)
_cell_length_c                   22.434(5)
_cell_angle_alpha                84.231(5)
_cell_angle_beta                 84.177(5)
_cell_angle_gamma                89.834(5)
_cell_volume                     1787.9(6)
_cell_formula_units_Z            4
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    2079
_cell_measurement_theta_min      4.901
_cell_measurement_theta_max      40.883

_exptl_crystal_description       prismatic
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.186
_exptl_crystal_size_mid          0.145
_exptl_crystal_size_min          0.121
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.605
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             856
_exptl_absorpt_coefficient_mu    4.536
_exptl_absorpt_correction_type   empirical
_exptl_absorpt_correction_T_min  0.11579
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_process_details   sadabs

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      293(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  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            10743
_diffrn_reflns_av_R_equivalents  0.0383
_diffrn_reflns_av_sigmaI/netI    0.0912
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_l_min       -27
_diffrn_reflns_limit_l_max       25
_diffrn_reflns_theta_min         0.92
_diffrn_reflns_theta_max         26.00
_reflns_number_total             6983
_reflns_number_gt                4295
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Bruker SMART'
_computing_cell_refinement       'Bruker SMART'
_computing_data_reduction        'Bruker SHELXTL'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_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)+(0.1075P)²+5.6999P] 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       ?
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         6983
_refine_ls_number_parameters     416
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.1242
_refine_ls_R_factor_gt           0.0788
_refine_ls_wR_factor_ref         0.2416
_refine_ls_wR_factor_gt          0.2136
_refine_ls_goodness_of_fit_ref   1.032
_refine_ls_restrained_S_all      1.032
_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
Br1 Br 0.43934(18) -0.36523(10) 0.12019(6) 0.0828(4) Uani 1 1 d . . .
Br2 Br 1.00692(17) 0.47092(11) 0.09980(6) 0.0858(4) Uani 1 1 d . . .
Br3 Br 0.57052(17) 0.18148(9) 0.38048(5) 0.0757(4) Uani 1 1 d . . .
Br4 Br -0.03291(14) 0.99081(10) 0.41003(4) 0.0665(3) Uani 1 1 d . . .
O1 O 0.2582(10) 0.1181(7) 0.2009(3) 0.0722(19) Uani 1 1 d . . .
O2 O 0.7476(9) 0.7004(6) 0.3003(3) 0.0672(18) Uani 1 1 d . . .
C1 C 0.2976(11) 0.0087(8) 0.1859(4) 0.050(2) Uani 1 1 d . . .
C2 C 0.2854(13) -0.0958(11) 0.2254(4) 0.069(3) Uani 1 1 d . . .
H2 H 0.2504 -0.0902 0.2661 0.083 Uiso 1 1 calc R . .
C3 C 0.3229(13) -0.2058(9) 0.2066(5) 0.064(3) Uani 1 1 d . . .
H3 H 0.3109 -0.2740 0.2338 0.077 Uiso 1 1 calc R . .
C4 C 0.3790(11) -0.2140(9) 0.1463(4) 0.057(2) Uani 1 1 d . . .
C5 C 0.3970(11) -0.1142(8) 0.1058(3) 0.049(2) Uani 1 1 d . . .
H5 H 0.4351 -0.1214 0.0654 0.059 Uiso 1 1 calc R . .
C6 C 0.3573(11) 0.0004(9) 0.1253(4) 0.053(2) Uani 1 1 d . . .
C7 C 0.3731(10) 0.1095(7) 0.0817(3) 0.0425(18) Uani 1 1 d . . .
C8 C 0.5245(10) 0.1984(7) 0.0879(3) 0.0433(18) Uani 1 1 d . . .
C9 C 0.5280(12) 0.3102(8) 0.0568(4) 0.057(2) Uani 1 1 d . . .
H9 H 0.4316 0.3311 0.0330 0.068 Uiso 1 1 calc R . .
C10 C 0.6679(13) 0.3927(8) 0.0593(4) 0.062(2) Uani 1 1 d . . .
H10 H 0.6666 0.4677 0.0378 0.074 Uiso 1 1 calc R . .
C11 C 0.8112(13) 0.3603(8) 0.0951(4) 0.058(2) Uani 1 1 d . . .
C12 C 0.8098(12) 0.2508(8) 0.1284(4) 0.052(2) Uani 1 1 d . . .
H12 H 0.9048 0.2308 0.1529 0.063 Uiso 1 1 calc R . .
C13 C 0.6660(11) 0.1707(8) 0.1252(4) 0.050(2) Uani 1 1 d . . .
H13 H 0.6637 0.0972 0.1484 0.060 Uiso 1 1 calc R . .
C14 C 0.2626(11) 0.1250(8) 0.0389(4) 0.049(2) Uani 1 1 d . . .
C15 C 0.1557(12) 0.1430(8) -0.0033(4) 0.050(2) Uani 1 1 d . . .
C16 C 0.1132(12) 0.1293(9) -0.0646(4) 0.059(2) Uani 1 1 d . . .
H16A H 0.0778 0.0504 -0.0736 0.070 Uiso 1 1 calc R . .
H16B H 0.1852 0.1770 -0.0974 0.070 Uiso 1 1 calc R . .
C17 C -0.0221(13) 0.1933(10) -0.0229(4) 0.064(2) Uani 1 1 d . . .
H17A H -0.0309 0.2794 -0.0305 0.076 Uiso 1 1 calc R . .
H17B H -0.1384 0.1527 -0.0067 0.076 Uiso 1 1 calc R . .
C18 C 0.2090(18) 0.1348(12) 0.2626(5) 0.086(3) Uani 1 1 d . . .
H18A H 0.3069 0.1020 0.2862 0.103 Uiso 1 1 calc R . .
H18B H 0.0936 0.0914 0.2769 0.103 Uiso 1 1 calc R . .
C19 C 0.184(2) 0.2587(16) 0.2718(6) 0.108(5) Uani 1 1 d D . .
H19 H 0.1193 0.2760 0.3080 0.130 Uiso 1 1 calc R . .
C20 C 0.244(2) 0.3489(15) 0.2338(8) 0.126(5) Uani 1 1 d D . .
H20A H 0.3095 0.3355 0.1971 0.151 Uiso 1 1 calc R . .
H20B H 0.2220 0.4266 0.2433 0.151 Uiso 1 1 calc R . .
C21 C 0.7116(11) 0.5811(8) 0.3155(4) 0.051(2) Uani 1 1 d . . .
C22 C 0.7301(14) 0.4955(10) 0.2754(4) 0.066(3) Uani 1 1 d . . .
H22 H 0.7686 0.5181 0.2350 0.079 Uiso 1 1 calc R . .
C23 C 0.6921(14) 0.3757(9) 0.2947(4) 0.061(2) Uani 1 1 d . . .
H23 H 0.7081 0.3178 0.2678 0.073 Uiso 1 1 calc R . .
C24 C 0.6310(11) 0.3451(7) 0.3536(4) 0.0487(19) Uani 1 1 d . . .
C25 C 0.6144(10) 0.4288(8) 0.3943(4) 0.0459(19) Uani 1 1 d . . .
H25 H 0.5784 0.4051 0.4348 0.055 Uiso 1 1 calc R . .
C26 C 0.6508(10) 0.5473(7) 0.3756(3) 0.0411(18) Uani 1 1 d . . .
C27 C 0.6269(10) 0.6386(7) 0.4200(3) 0.0373(16) Uani 1 1 d . . .
C28 C 0.4721(9) 0.7268(7) 0.4147(3) 0.0386(17) Uani 1 1 d . . .
C29 C 0.4685(11) 0.8291(7) 0.4453(4) 0.0461(19) Uani 1 1 d . . .
H29 H 0.5672 0.8442 0.4675 0.055 Uiso 1 1 calc R . .
C30 C 0.3214(12) 0.9080(7) 0.4431(4) 0.049(2) Uani 1 1 d . . .
H30 H 0.3214 0.9767 0.4630 0.059 Uiso 1 1 calc R . .
C31 C 0.1726(11) 0.8830(7) 0.4108(3) 0.0459(19) Uani 1 1 d . . .
C32 C 0.1713(11) 0.7851(8) 0.3804(4) 0.049(2) Uani 1 1 d . . .
H32 H 0.0714 0.7704 0.3586 0.059 Uiso 1 1 calc R . .
C33 C 0.3220(10) 0.7066(7) 0.3822(3) 0.0413(17) Uani 1 1 d . . .
H33 H 0.3222 0.6394 0.3612 0.050 Uiso 1 1 calc R . .
C34 C 0.7354(11) 0.6381(7) 0.4636(3) 0.0437(18) Uani 1 1 d . . .
C35 C 0.8394(10) 0.6369(7) 0.5069(3) 0.0435(18) Uani 1 1 d . . .
C36 C 0.8794(12) 0.5953(8) 0.5681(4) 0.053(2) Uani 1 1 d . . .
H36A H 0.9225 0.5138 0.5756 0.063 Uiso 1 1 calc R . .
H36B H 0.8007 0.6244 0.6013 0.063 Uiso 1 1 calc R . .
C37 C 1.0093(12) 0.6832(9) 0.5294(4) 0.059(2) Uani 1 1 d . . .
H37A H 1.0084 0.7653 0.5391 0.071 Uiso 1 1 calc R . .
H37B H 1.1303 0.6546 0.5134 0.071 Uiso 1 1 calc R . .
C38 C 0.8063(14) 0.7395(9) 0.2396(4) 0.062(2) Uani 1 1 d . . .
H38A H 0.7217 0.7092 0.2134 0.075 Uiso 1 1 calc R . .
H38B H 0.9318 0.7110 0.2285 0.075 Uiso 1 1 calc R . .
C39 C 0.8041(15) 0.8739(10) 0.2337(4) 0.071(3) Uani 1 1 d . . .
H39 H 0.8600 0.9122 0.1976 0.085 Uiso 1 1 calc R . .
C40 C 0.7344(16) 0.9407(10) 0.2725(5) 0.079(3) Uani 1 1 d . . .
H40A H 0.6768 0.9070 0.3094 0.095 Uiso 1 1 calc R . .
H40B H 0.7409 1.0234 0.2641 0.095 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
Br1 C4 1.890(10) . ?
Br2 C11 1.894(9) . ?
Br3 C24 1.915(9) . ?
Br4 C31 1.904(8) . ?
O1 C1 1.330(11) . ?
O1 C18 1.425(12) . ?
O2 C21 1.369(11) . ?
O2 C38 1.411(10) . ?
C1 C2 1.396(13) . ?
C1 C6 1.396(11) . ?
C2 C3 1.365(15) . ?
C2 H2 0.9300 . ?
C3 C4 1.383(14) . ?
C3 H3 0.9300 . ?
C4 C5 1.370(13) . ?
C5 C6 1.421(12) . ?
C5 H5 0.9300 . ?
C6 C7 1.487(12) . ?
C7 C14 1.303(11) . ?
C7 C8 1.503(10) . ?
C8 C9 1.376(12) . ?
C8 C13 1.394(11) . ?
C9 C10 1.376(12) . ?
C9 H9 0.9300 . ?
C10 C11 1.392(13) . ?
C10 H10 0.9300 . ?
C11 C12 1.374(12) . ?
C12 C13 1.382(11) . ?
C12 H12 0.9300 . ?
C13 H13 0.9300 . ?
C14 C15 1.278(11) . ?
C15 C16 1.460(11) . ?
C15 C17 1.480(12) . ?
C16 C17 1.509(14) . ?
C16 H16A 0.9700 . ?
C16 H16B 0.9700 . ?
C17 H17A 0.9700 . ?
C17 H17B 0.9700 . ?
C18 C19 1.437(19) . ?
C18 H18A 0.9700 . ?
C18 H18B 0.9700 . ?
C19 C20 1.303(15) . ?
C19 H19 0.9300 . ?
C20 H20A 0.9300 . ?
C20 H20B 0.9300 . ?
C21 C22 1.379(13) . ?
C21 C26 1.390(11) . ?
C22 C23 1.393(14) . ?
C22 H22 0.9300 . ?
C23 C24 1.360(12) . ?
C23 H23 0.9300 . ?
C24 C25 1.372(11) . ?
C25 C26 1.375(11) . ?
C25 H25 0.9300 . ?
C26 C27 1.498(10) . ?
C27 C34 1.309(10) . ?
C27 C28 1.491(10) . ?
C28 C33 1.390(10) . ?
C28 C29 1.397(11) . ?
C29 C30 1.376(11) . ?
C29 H29 0.9300 . ?
C30 C31 1.393(11) . ?
C30 H30 0.9300 . ?
C31 C32 1.353(11) . ?
C32 C33 1.393(11) . ?
C32 H32 0.9300 . ?
C33 H33 0.9300 . ?
C34 C35 1.282(11) . ?
C35 C36 1.461(11) . ?
C35 C37 1.477(11) . ?
C36 C37 1.506(13) . ?
C36 H36A 0.9700 . ?
C36 H36B 0.9700 . ?
C37 H37A 0.9700 . ?
C37 H37B 0.9700 . ?
C38 C39 1.504(15) . ?
C38 H38A 0.9700 . ?
C38 H38B 0.9700 . ?
C39 C40 1.271(15) . ?
C39 H39 0.9300 . ?
C40 H40A 0.9300 . ?
C40 H40B 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
C1 O1 C18 119.1(8) . . ?
C21 O2 C38 118.3(7) . . ?
O1 C1 C2 125.7(8) . . ?
O1 C1 C6 115.8(8) . . ?
C2 C1 C6 118.6(9) . . ?
C3 C2 C1 122.5(9) . . ?
C3 C2 H2 118.7 . . ?
C1 C2 H2 118.7 . . ?
C2 C3 C4 118.8(9) . . ?
C2 C3 H3 120.6 . . ?
C4 C3 H3 120.6 . . ?
C5 C4 C3 121.2(9) . . ?
C5 C4 Br1 119.6(7) . . ?
C3 C4 Br1 119.2(7) . . ?
C4 C5 C6 120.0(8) . . ?
C4 C5 H5 120.0 . . ?
C6 C5 H5 120.0 . . ?
C1 C6 C5 118.9(8) . . ?
C1 C6 C7 120.4(8) . . ?
C5 C6 C7 120.7(7) . . ?
C14 C7 C6 120.8(7) . . ?
C14 C7 C8 121.7(7) . . ?
C6 C7 C8 117.5(7) . . ?
C9 C8 C13 117.6(7) . . ?
C9 C8 C7 121.0(7) . . ?
C13 C8 C7 121.4(7) . . ?
C10 C9 C8 122.9(8) . . ?
C10 C9 H9 118.5 . . ?
C8 C9 H9 118.5 . . ?
C9 C10 C11 117.9(8) . . ?
C9 C10 H10 121.0 . . ?
C11 C10 H10 121.0 . . ?
C12 C11 C10 121.0(8) . . ?
C12 C11 Br2 119.6(7) . . ?
C10 C11 Br2 119.4(7) . . ?
C11 C12 C13 119.5(8) . . ?
C11 C12 H12 120.2 . . ?
C13 C12 H12 120.2 . . ?
C12 C13 C8 121.0(8) . . ?
C12 C13 H13 119.5 . . ?
C8 C13 H13 119.5 . . ?
C15 C14 C7 178.6(9) . . ?
C14 C15 C16 150.7(9) . . ?
C14 C15 C17 147.6(9) . . ?
C16 C15 C17 61.8(6) . . ?
C15 C16 C17 59.8(6) . . ?
C15 C16 H16A 117.8 . . ?
C17 C16 H16A 117.8 . . ?
C15 C16 H16B 117.8 . . ?
C17 C16 H16B 117.8 . . ?
H16A C16 H16B 114.9 . . ?
C15 C17 C16 58.5(6) . . ?
C15 C17 H17A 117.9 . . ?
C16 C17 H17A 117.9 . . ?
C15 C17 H17B 117.9 . . ?
C16 C17 H17B 117.9 . . ?
H17A C17 H17B 115.1 . . ?
O1 C18 C19 112.2(11) . . ?
O1 C18 H18A 109.2 . . ?
C19 C18 H18A 109.2 . . ?
O1 C18 H18B 109.2 . . ?
C19 C18 H18B 109.2 . . ?
H18A C18 H18B 107.9 . . ?
C20 C19 C18 125.5(15) . . ?
C20 C19 H19 117.3 . . ?
C18 C19 H19 117.3 . . ?
C19 C20 H20A 120.0 . . ?
C19 C20 H20B 120.0 . . ?
H20A C20 H20B 120.0 . . ?
O2 C21 C22 124.4(8) . . ?
O2 C21 C26 116.2(7) . . ?
C22 C21 C26 119.4(9) . . ?
C21 C22 C23 120.8(9) . . ?
C21 C22 H22 119.6 . . ?
C23 C22 H22 119.6 . . ?
C24 C23 C22 118.6(8) . . ?
C24 C23 H23 120.7 . . ?
C22 C23 H23 120.7 . . ?
C23 C24 C25 121.3(8) . . ?
C23 C24 Br3 119.2(6) . . ?
C25 C24 Br3 119.5(7) . . ?
C24 C25 C26 120.4(7) . . ?
C24 C25 H25 119.8 . . ?
C26 C25 H25 119.8 . . ?
C25 C26 C21 119.4(7) . . ?
C25 C26 C27 120.1(7) . . ?
C21 C26 C27 120.5(7) . . ?
C34 C27 C28 120.9(7) . . ?
C34 C27 C26 120.6(7) . . ?
C28 C27 C26 118.4(6) . . ?
C33 C28 C29 117.9(7) . . ?
C33 C28 C27 121.2(7) . . ?
C29 C28 C27 120.7(6) . . ?
C30 C29 C28 121.2(7) . . ?
C30 C29 H29 119.4 . . ?
C28 C29 H29 119.4 . . ?
C29 C30 C31 118.9(7) . . ?
C29 C30 H30 120.6 . . ?
C31 C30 H30 120.6 . . ?
C32 C31 C30 121.7(7) . . ?
C32 C31 Br4 119.9(6) . . ?
C30 C31 Br4 118.3(6) . . ?
C31 C32 C33 119.0(7) . . ?
C31 C32 H32 120.5 . . ?
C33 C32 H32 120.5 . . ?
C28 C33 C32 121.3(7) . . ?
C28 C33 H33 119.3 . . ?
C32 C33 H33 119.3 . . ?
C35 C34 C27 179.0(8) . . ?
C34 C35 C36 150.9(8) . . ?
C34 C35 C37 147.5(8) . . ?
C36 C35 C37 61.6(6) . . ?
C35 C36 C37 59.7(5) . . ?
C35 C36 H36A 117.8 . . ?
C37 C36 H36A 117.8 . . ?
C35 C36 H36B 117.8 . . ?
C37 C36 H36B 117.8 . . ?
H36A C36 H36B 114.9 . . ?
C35 C37 C36 58.7(5) . . ?
C35 C37 H37A 117.9 . . ?
C36 C37 H37A 117.9 . . ?
C35 C37 H37B 117.9 . . ?
C36 C37 H37B 117.9 . . ?
H37A C37 H37B 115.1 . . ?
O2 C38 C39 107.1(8) . . ?
O2 C38 H38A 110.3 . . ?
C39 C38 H38A 110.3 . . ?
O2 C38 H38B 110.3 . . ?
C39 C38 H38B 110.3 . . ?
H38A C38 H38B 108.5 . . ?
C40 C39 C38 127.2(10) . . ?
C40 C39 H39 116.4 . . ?
C38 C39 H39 116.4 . . ?
C39 C40 H40A 120.0 . . ?
C39 C40 H40B 120.0 . . ?
H40A C40 H40B 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
C18 O1 C1 C2 3.8(14) . . . . ?
C18 O1 C1 C6 -175.7(9) . . . . ?
O1 C1 C2 C3 178.1(9) . . . . ?
C6 C1 C2 C3 -2.5(14) . . . . ?
C1 C2 C3 C4 1.4(14) . . . . ?
C2 C3 C4 C5 -0.1(13) . . . . ?
C2 C3 C4 Br1 177.9(7) . . . . ?
C3 C4 C5 C6 -0.1(12) . . . . ?
Br1 C4 C5 C6 -178.1(6) . . . . ?
O1 C1 C6 C5 -178.3(7) . . . . ?
C2 C1 C6 C5 2.2(12) . . . . ?
O1 C1 C6 C7 -0.2(11) . . . . ?
C2 C1 C6 C7 -179.7(8) . . . . ?
C4 C5 C6 C1 -0.9(12) . . . . ?
C4 C5 C6 C7 -179.0(7) . . . . ?
C1 C6 C7 C14 -113.3(10) . . . . ?
C5 C6 C7 C14 64.7(11) . . . . ?
C1 C6 C7 C8 68.5(10) . . . . ?
C5 C6 C7 C8 -113.5(9) . . . . ?
C14 C7 C8 C9 13.4(12) . . . . ?
C6 C7 C8 C9 -168.4(8) . . . . ?
C14 C7 C8 C13 -166.5(8) . . . . ?
C6 C7 C8 C13 11.6(11) . . . . ?
C13 C8 C9 C10 2.6(13) . . . . ?
C7 C8 C9 C10 -177.4(8) . . . . ?
C8 C9 C10 C11 0.0(15) . . . . ?
C9 C10 C11 C12 -2.0(14) . . . . ?
C9 C10 C11 Br2 179.9(7) . . . . ?
C10 C11 C12 C13 1.4(14) . . . . ?
Br2 C11 C12 C13 179.5(7) . . . . ?
C11 C12 C13 C8 1.3(13) . . . . ?
C9 C8 C13 C12 -3.2(13) . . . . ?
C7 C8 C13 C12 176.8(8) . . . . ?
C6 C7 C14 C15 168(36) . . . . ?
C8 C7 C14 C15 -14(37) . . . . ?
C7 C14 C15 C16 104(36) . . . . ?
C7 C14 C15 C17 -78(36) . . . . ?
C14 C15 C16 C17 178.7(18) . . . . ?
C14 C15 C17 C16 -178.8(17) . . . . ?
C1 O1 C18 C19 175.8(10) . . . . ?
O1 C18 C19 C20 -17(2) . . . . ?
C38 O2 C21 C22 0.6(13) . . . . ?
C38 O2 C21 C26 -178.8(7) . . . . ?
O2 C21 C22 C23 179.4(9) . . . . ?
C26 C21 C22 C23 -1.2(14) . . . . ?
C21 C22 C23 C24 1.8(15) . . . . ?
C22 C23 C24 C25 -2.8(13) . . . . ?
C22 C23 C24 Br3 178.1(7) . . . . ?
C23 C24 C25 C26 3.2(12) . . . . ?
Br3 C24 C25 C26 -177.7(6) . . . . ?
C24 C25 C26 C21 -2.5(11) . . . . ?
C24 C25 C26 C27 178.2(7) . . . . ?
O2 C21 C26 C25 -179.1(7) . . . . ?
C22 C21 C26 C25 1.5(12) . . . . ?
O2 C21 C26 C27 0.2(11) . . . . ?
C22 C21 C26 C27 -179.2(8) . . . . ?
C25 C26 C27 C34 65.8(10) . . . . ?
C21 C26 C27 C34 -113.5(9) . . . . ?
C25 C26 C27 C28 -111.7(8) . . . . ?
C21 C26 C27 C28 69.0(9) . . . . ?
C34 C27 C28 C33 -159.4(7) . . . . ?
C26 C27 C28 C33 18.2(10) . . . . ?
C34 C27 C28 C29 17.0(11) . . . . ?
C26 C27 C28 C29 -165.4(7) . . . . ?
C33 C28 C29 C30 -0.3(11) . . . . ?
C27 C28 C29 C30 -176.7(7) . . . . ?
C28 C29 C30 C31 1.3(12) . . . . ?
C29 C30 C31 C32 -1.7(12) . . . . ?
C29 C30 C31 Br4 178.4(6) . . . . ?
C30 C31 C32 C33 0.8(12) . . . . ?
Br4 C31 C32 C33 -179.2(6) . . . . ?
C29 C28 C33 C32 -0.6(11) . . . . ?
C27 C28 C33 C32 175.8(7) . . . . ?
C31 C32 C33 C28 0.3(12) . . . . ?
C28 C27 C34 C35 69(53) . . . . ?
C26 C27 C34 C35 -109(53) . . . . ?
C27 C34 C35 C36 21(54) . . . . ?
C27 C34 C35 C37 -157(52) . . . . ?
C34 C35 C36 C37 -178.7(17) . . . . ?
C34 C35 C37 C36 178.8(16) . . . . ?
C21 O2 C38 C39 170.7(7) . . . . ?
O2 C38 C39 C40 -10.6(15) . . . . ?

_diffrn_measured_fraction_theta_max 0.993
_diffrn_reflns_theta_full        26.00
_diffrn_measured_fraction_theta_full 0.993
_refine_diff_density_max         1.180
_refine_diff_density_min         -0.621
_refine_diff_density_rms         0.136
####################################################################### 
# 
# 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_213
_database_code_depnum_ccdc_archive 'CCDC 996499'
_audit_update_record             
;
2014-04-10 deposited with the CCDC.
2015-06-23 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C25 H36 O'
_chemical_formula_sum            'C25 H36 O'
_chemical_formula_weight         352.54

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           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                   14.4666(5)
_cell_length_b                   10.0707(3)
_cell_length_c                   16.4037(6)
_cell_angle_alpha                90.00
_cell_angle_beta                 109.5080(10)
_cell_angle_gamma                90.00
_cell_volume                     2252.65(13)
_cell_formula_units_Z            4
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    9949
_cell_measurement_theta_min      4.39
_cell_measurement_theta_max      66.97

_exptl_crystal_description       block
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.50
_exptl_crystal_size_mid          0.32
_exptl_crystal_size_min          0.24
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.039
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             776
_exptl_absorpt_coefficient_mu    0.457
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.6009
_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            14329
_diffrn_reflns_av_R_equivalents  0.0267
_diffrn_reflns_av_sigmaI/netI    0.0292
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_theta_min         5.24
_diffrn_reflns_theta_max         66.47
_reflns_number_total             3911
_reflns_number_gt                3717
_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)+(0.0968P)²+0.4510P] 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       0.0161(12)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         3911
_refine_ls_number_parameters     236
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0599
_refine_ls_R_factor_gt           0.0584
_refine_ls_wR_factor_ref         0.1702
_refine_ls_wR_factor_gt          0.1683
_refine_ls_goodness_of_fit_ref   1.062
_refine_ls_restrained_S_all      1.062
_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 0.57659(8) 0.52269(10) 0.19270(7) 0.0551(3) Uani 1 1 d . . .
C1 C 0.72609(11) 0.63911(15) 0.26284(9) 0.0502(4) Uani 1 1 d . . .
C2 C 0.78323(11) 0.74979(16) 0.26212(9) 0.0529(4) Uani 1 1 d . . .
H2A H 0.8436 0.7576 0.3058 0.064 Uiso 1 1 calc R . .
C3 C 0.75554(11) 0.84959(16) 0.20008(10) 0.0529(4) Uani 1 1 d . . .
C4 C 0.66659(11) 0.83476(16) 0.13418(10) 0.0528(4) Uani 1 1 d . . .
H4A H 0.6470 0.8992 0.0912 0.063 Uiso 1 1 calc R . .
C5 C 0.60575(10) 0.72627(15) 0.13041(9) 0.0485(4) Uani 1 1 d . . .
C6 C 0.51468(11) 0.70116(16) 0.05636(10) 0.0539(4) Uani 1 1 d . . .
C7 C 0.45124(11) 0.61076(17) 0.06557(11) 0.0555(4) Uani 1 1 d . . .
C8 C 0.47450(11) 0.55073(17) 0.15311(11) 0.0575(4) Uani 1 1 d . . .
C9 C 0.63547(10) 0.63132(14) 0.19625(9) 0.0477(4) Uani 1 1 d . . .
C10 C 0.35908(12) 0.56732(19) -0.00537(12) 0.0641(5) Uani 1 1 d . . .
H10A H 0.3663 0.5867 -0.0609 0.077 Uiso 1 1 calc R . .
H10B H 0.3523 0.4719 -0.0017 0.077 Uiso 1 1 calc R . .
C11 C 0.26694(11) 0.63234(17) -0.00219(11) 0.0599(4) Uani 1 1 d . . .
H11A H 0.2733 0.7188 0.0189 0.072 Uiso 1 1 calc R . .
C12 C 0.17862(12) 0.58125(19) -0.02570(12) 0.0635(5) Uani 1 1 d . . .
C13 C 0.15643(18) 0.4424(3) -0.0591(2) 0.1192(11) Uani 1 1 d . . .
H13A H 0.2160 0.3996 -0.0585 0.179 Uiso 1 1 calc R . .
H13B H 0.1112 0.4446 -0.1172 0.179 Uiso 1 1 calc R . .
H13C H 0.1279 0.3939 -0.0230 0.179 Uiso 1 1 calc R . .
C14 C 0.09221(13) 0.6612(3) -0.02308(15) 0.0851(6) Uani 1 1 d . . .
H14A H 0.1137 0.7480 -0.0006 0.128 Uiso 1 1 calc R . .
H14B H 0.0618 0.6177 0.0135 0.128 Uiso 1 1 calc R . .
H14C H 0.0457 0.6689 -0.0805 0.128 Uiso 1 1 calc R . .
C15 C 0.42343(15) 0.5942(2) 0.21478(15) 0.0784(6) Uani 1 1 d . . .
H15A H 0.4629 0.6063 0.2750 0.094 Uiso 1 1 calc R . .
H15B H 0.3685 0.6548 0.1934 0.094 Uiso 1 1 calc R . .
C16 C 0.41112(16) 0.4555(2) 0.17903(15) 0.0802(6) Uani 1 1 d . . .
H16A H 0.4429 0.3840 0.2179 0.096 Uiso 1 1 calc R . .
H16B H 0.3485 0.4325 0.1363 0.096 Uiso 1 1 calc R . .
C17 C 0.50134(13) 0.7751(2) -0.02674(12) 0.0718(5) Uani 1 1 d . . .
H17A H 0.4401 0.7501 -0.0691 0.108 Uiso 1 1 calc R . .
H17B H 0.5541 0.7535 -0.0476 0.108 Uiso 1 1 calc R . .
H17C H 0.5014 0.8689 -0.0164 0.108 Uiso 1 1 calc R . .
C18 C 0.82453(13) 0.96743(19) 0.20559(12) 0.0652(5) Uani 1 1 d . . .
C19 C 0.7733(2) 1.0807(3) 0.14580(16) 0.1106(10) Uani 1 1 d . . .
H19A H 0.7513 1.0501 0.0870 0.166 Uiso 1 1 calc R . .
H19B H 0.8184 1.1530 0.1519 0.166 Uiso 1 1 calc R . .
H19C H 0.7181 1.1102 0.1609 0.166 Uiso 1 1 calc R . .
C20 C 0.85680(15) 1.0276(2) 0.29706(14) 0.0781(6) Uani 1 1 d . . .
H20A H 0.8004 1.0604 0.3090 0.117 Uiso 1 1 calc R . .
H20B H 0.9017 1.0993 0.3006 0.117 Uiso 1 1 calc R . .
H20C H 0.8885 0.9606 0.3386 0.117 Uiso 1 1 calc R . .
C21 C 0.9145(2) 0.9180(3) 0.1871(3) 0.1358(14) Uani 1 1 d . . .
H21A H 0.8951 0.8805 0.1300 0.204 Uiso 1 1 calc R . .
H21B H 0.9468 0.8515 0.2287 0.204 Uiso 1 1 calc R . .
H21C H 0.9585 0.9909 0.1907 0.204 Uiso 1 1 calc R . .
C22 C 0.76128(14) 0.53033(17) 0.33249(11) 0.0624(5) Uani 1 1 d . . .
C23 C 0.68845(19) 0.5154(3) 0.38148(14) 0.0901(7) Uani 1 1 d . . .
H23A H 0.6247 0.4947 0.3414 0.135 Uiso 1 1 calc R . .
H23B H 0.6853 0.5970 0.4107 0.135 Uiso 1 1 calc R . .
H23C H 0.7096 0.4450 0.4231 0.135 Uiso 1 1 calc R . .
C24 C 0.77116(17) 0.39933(19) 0.28928(15) 0.0822(6) Uani 1 1 d . . .
H24A H 0.7089 0.3755 0.2479 0.123 Uiso 1 1 calc R . .
H24B H 0.7922 0.3310 0.3324 0.123 Uiso 1 1 calc R . .
H24C H 0.8186 0.4091 0.2605 0.123 Uiso 1 1 calc R . .
C25 C 0.86197(17) 0.5640(2) 0.39861(14) 0.0870(7) Uani 1 1 d . . .
H25A H 0.9089 0.5745 0.3693 0.130 Uiso 1 1 calc R . .
H25B H 0.8825 0.4935 0.4401 0.130 Uiso 1 1 calc R . .
H25C H 0.8574 0.6452 0.4277 0.130 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 C9 1.3757(18) . ?
O1 C8 1.4291(19) . ?
C1 C2 1.390(2) . ?
C1 C9 1.401(2) . ?
C1 C22 1.542(2) . ?
C2 C3 1.391(2) . ?
C2 H2A 0.9300 . ?
C3 C4 1.385(2) . ?
C3 C18 1.534(2) . ?
C4 C5 1.391(2) . ?
C4 H4A 0.9300 . ?
C5 C9 1.398(2) . ?
C5 C6 1.485(2) . ?
C6 C7 1.337(2) . ?
C6 C17 1.508(2) . ?
C7 C8 1.489(2) . ?
C7 C10 1.512(2) . ?
C8 C16 1.483(2) . ?
C8 C15 1.503(2) . ?
C10 C11 1.502(2) . ?
C10 H10A 0.9700 . ?
C10 H10B 0.9700 . ?
C11 C12 1.310(2) . ?
C11 H11A 0.9300 . ?
C12 C13 1.497(3) . ?
C12 C14 1.499(3) . ?
C13 H13A 0.9600 . ?
C13 H13B 0.9600 . ?
C13 H13C 0.9600 . ?
C14 H14A 0.9600 . ?
C14 H14B 0.9600 . ?
C14 H14C 0.9600 . ?
C15 C16 1.502(3) . ?
C15 H15A 0.9700 . ?
C15 H15B 0.9700 . ?
C16 H16A 0.9700 . ?
C16 H16B 0.9700 . ?
C17 H17A 0.9600 . ?
C17 H17B 0.9600 . ?
C17 H17C 0.9600 . ?
C18 C21 1.516(3) . ?
C18 C19 1.525(3) . ?
C18 C20 1.539(3) . ?
C19 H19A 0.9600 . ?
C19 H19B 0.9600 . ?
C19 H19C 0.9600 . ?
C20 H20A 0.9600 . ?
C20 H20B 0.9600 . ?
C20 H20C 0.9600 . ?
C21 H21A 0.9600 . ?
C21 H21B 0.9600 . ?
C21 H21C 0.9600 . ?
C22 C24 1.527(3) . ?
C22 C23 1.531(3) . ?
C22 C25 1.536(3) . ?
C23 H23A 0.9600 . ?
C23 H23B 0.9600 . ?
C23 H23C 0.9600 . ?
C24 H24A 0.9600 . ?
C24 H24B 0.9600 . ?
C24 H24C 0.9600 . ?
C25 H25A 0.9600 . ?
C25 H25B 0.9600 . ?
C25 H25C 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
C9 O1 C8 113.17(12) . . ?
C2 C1 C9 116.28(13) . . ?
C2 C1 C22 121.73(14) . . ?
C9 C1 C22 121.99(14) . . ?
C1 C2 C3 123.98(14) . . ?
C1 C2 H2A 118.0 . . ?
C3 C2 H2A 118.0 . . ?
C4 C3 C2 117.31(14) . . ?
C4 C3 C18 123.11(14) . . ?
C2 C3 C18 119.55(14) . . ?
C3 C4 C5 121.90(14) . . ?
C3 C4 H4A 119.0 . . ?
C5 C4 H4A 119.0 . . ?
C4 C5 C9 118.41(13) . . ?
C4 C5 C6 123.04(14) . . ?
C9 C5 C6 118.37(13) . . ?
C7 C6 C5 118.58(14) . . ?
C7 C6 C17 123.59(14) . . ?
C5 C6 C17 117.77(14) . . ?
C6 C7 C8 116.29(14) . . ?
C6 C7 C10 124.90(16) . . ?
C8 C7 C10 118.80(14) . . ?
O1 C8 C16 112.71(15) . . ?
O1 C8 C7 112.63(13) . . ?
C16 C8 C7 125.19(16) . . ?
O1 C8 C15 114.67(15) . . ?
C16 C8 C15 60.38(14) . . ?
C7 C8 C15 121.80(16) . . ?
O1 C9 C5 118.99(13) . . ?
O1 C9 C1 118.86(13) . . ?
C5 C9 C1 122.03(13) . . ?
C11 C10 C7 114.32(14) . . ?
C11 C10 H10A 108.7 . . ?
C7 C10 H10A 108.7 . . ?
C11 C10 H10B 108.7 . . ?
C7 C10 H10B 108.7 . . ?
H10A C10 H10B 107.6 . . ?
C12 C11 C10 127.46(16) . . ?
C12 C11 H11A 116.3 . . ?
C10 C11 H11A 116.3 . . ?
C11 C12 C13 122.91(18) . . ?
C11 C12 C14 121.41(18) . . ?
C13 C12 C14 115.65(17) . . ?
C12 C13 H13A 109.5 . . ?
C12 C13 H13B 109.5 . . ?
H13A C13 H13B 109.5 . . ?
C12 C13 H13C 109.5 . . ?
H13A C13 H13C 109.5 . . ?
H13B C13 H13C 109.5 . . ?
C12 C14 H14A 109.5 . . ?
C12 C14 H14B 109.5 . . ?
H14A C14 H14B 109.5 . . ?
C12 C14 H14C 109.5 . . ?
H14A C14 H14C 109.5 . . ?
H14B C14 H14C 109.5 . . ?
C16 C15 C8 59.16(12) . . ?
C16 C15 H15A 117.9 . . ?
C8 C15 H15A 117.9 . . ?
C16 C15 H15B 117.9 . . ?
C8 C15 H15B 117.9 . . ?
H15A C15 H15B 115.0 . . ?
C8 C16 C15 60.47(12) . . ?
C8 C16 H16A 117.7 . . ?
C15 C16 H16A 117.7 . . ?
C8 C16 H16B 117.7 . . ?
C15 C16 H16B 117.7 . . ?
H16A C16 H16B 114.8 . . ?
C6 C17 H17A 109.5 . . ?
C6 C17 H17B 109.5 . . ?
H17A C17 H17B 109.5 . . ?
C6 C17 H17C 109.5 . . ?
H17A C17 H17C 109.5 . . ?
H17B C17 H17C 109.5 . . ?
C21 C18 C19 112.4(2) . . ?
C21 C18 C3 108.64(17) . . ?
C19 C18 C3 111.96(16) . . ?
C21 C18 C20 108.9(2) . . ?
C19 C18 C20 104.87(18) . . ?
C3 C18 C20 109.98(15) . . ?
C18 C19 H19A 109.5 . . ?
C18 C19 H19B 109.5 . . ?
H19A C19 H19B 109.5 . . ?
C18 C19 H19C 109.5 . . ?
H19A C19 H19C 109.5 . . ?
H19B C19 H19C 109.5 . . ?
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 . . ?
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 . . ?
C24 C22 C23 110.25(18) . . ?
C24 C22 C25 107.77(16) . . ?
C23 C22 C25 107.93(17) . . ?
C24 C22 C1 109.20(14) . . ?
C23 C22 C1 110.13(15) . . ?
C25 C22 C1 111.53(15) . . ?
C22 C23 H23A 109.5 . . ?
C22 C23 H23B 109.5 . . ?
H23A C23 H23B 109.5 . . ?
C22 C23 H23C 109.5 . . ?
H23A C23 H23C 109.5 . . ?
H23B C23 H23C 109.5 . . ?
C22 C24 H24A 109.5 . . ?
C22 C24 H24B 109.5 . . ?
H24A C24 H24B 109.5 . . ?
C22 C24 H24C 109.5 . . ?
H24A C24 H24C 109.5 . . ?
H24B C24 H24C 109.5 . . ?
C22 C25 H25A 109.5 . . ?
C22 C25 H25B 109.5 . . ?
H25A C25 H25B 109.5 . . ?
C22 C25 H25C 109.5 . . ?
H25A C25 H25C 109.5 . . ?
H25B C25 H25C 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
C9 C1 C2 C3 -0.3(2) . . . . ?
C22 C1 C2 C3 179.00(15) . . . . ?
C1 C2 C3 C4 -1.7(2) . . . . ?
C1 C2 C3 C18 -179.97(15) . . . . ?
C2 C3 C4 C5 1.3(2) . . . . ?
C18 C3 C4 C5 179.49(15) . . . . ?
C3 C4 C5 C9 1.0(2) . . . . ?
C3 C4 C5 C6 -174.03(14) . . . . ?
C4 C5 C6 C7 -166.91(15) . . . . ?
C9 C5 C6 C7 18.0(2) . . . . ?
C4 C5 C6 C17 15.9(2) . . . . ?
C9 C5 C6 C17 -159.23(15) . . . . ?
C5 C6 C7 C8 4.9(2) . . . . ?
C17 C6 C7 C8 -178.06(16) . . . . ?
C5 C6 C7 C10 -175.62(14) . . . . ?
C17 C6 C7 C10 1.4(3) . . . . ?
C9 O1 C8 C16 -157.41(15) . . . . ?
C9 O1 C8 C7 54.23(17) . . . . ?
C9 O1 C8 C15 -90.83(17) . . . . ?
C6 C7 C8 O1 -40.5(2) . . . . ?
C10 C7 C8 O1 139.92(14) . . . . ?
C6 C7 C8 C16 175.78(18) . . . . ?
C10 C7 C8 C16 -3.8(3) . . . . ?
C6 C7 C8 C15 101.71(19) . . . . ?
C10 C7 C8 C15 -77.8(2) . . . . ?
C8 O1 C9 C5 -32.09(18) . . . . ?
C8 O1 C9 C1 151.81(14) . . . . ?
C4 C5 C9 O1 -179.17(13) . . . . ?
C6 C5 C9 O1 -3.9(2) . . . . ?
C4 C5 C9 C1 -3.2(2) . . . . ?
C6 C5 C9 C1 172.12(13) . . . . ?
C2 C1 C9 O1 178.77(12) . . . . ?
C22 C1 C9 O1 -0.5(2) . . . . ?
C2 C1 C9 C5 2.8(2) . . . . ?
C22 C1 C9 C5 -176.50(14) . . . . ?
C6 C7 C10 C11 -99.4(2) . . . . ?
C8 C7 C10 C11 80.1(2) . . . . ?
C7 C10 C11 C12 -147.80(19) . . . . ?
C10 C11 C12 C13 1.4(3) . . . . ?
C10 C11 C12 C14 -176.76(19) . . . . ?
O1 C8 C15 C16 -103.15(18) . . . . ?
C7 C8 C15 C16 115.31(19) . . . . ?
O1 C8 C16 C15 106.41(18) . . . . ?
C7 C8 C16 C15 -109.9(2) . . . . ?
C4 C3 C18 C21 -109.9(2) . . . . ?
C2 C3 C18 C21 68.3(3) . . . . ?
C4 C3 C18 C19 14.9(3) . . . . ?
C2 C3 C18 C19 -166.9(2) . . . . ?
C4 C3 C18 C20 131.07(17) . . . . ?
C2 C3 C18 C20 -50.8(2) . . . . ?
C2 C1 C22 C24 -117.27(18) . . . . ?
C9 C1 C22 C24 62.0(2) . . . . ?
C2 C1 C22 C23 121.54(18) . . . . ?
C9 C1 C22 C23 -59.2(2) . . . . ?
C2 C1 C22 C25 1.7(2) . . . . ?
C9 C1 C22 C25 -179.02(16) . . . . ?

_diffrn_measured_fraction_theta_max 0.988
_diffrn_reflns_theta_full        66.47
_diffrn_measured_fraction_theta_full 0.988
_refine_diff_density_max         0.268
_refine_diff_density_min         -0.220
_refine_diff_density_rms         0.051
####################################################################### 
# 
# 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_cd214202
_database_code_depnum_ccdc_archive 'CCDC 996502'
_audit_update_record             
;
2014-04-10 deposited with the CCDC.
2015-06-23 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2013
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C28 H34 O'
_chemical_formula_weight         386.55

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                   23.302(4)
_cell_length_b                   11.4445(17)
_cell_length_c                   18.904(3)
_cell_angle_alpha                90
_cell_angle_beta                 104.415(6)
_cell_angle_gamma                90
_cell_volume                     4882.7(14)
_cell_formula_units_Z            8
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    1100
_cell_measurement_theta_min      4.450
_cell_measurement_theta_max      38.031

_exptl_crystal_description       prismatic
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.052
_exptl_crystal_F_000             1680
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.211
_exptl_crystal_size_mid          0.165
_exptl_crystal_size_min          0.123
_exptl_absorpt_coefficient_mu    0.062
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.5492
_exptl_absorpt_correction_T_max  0.7457
_exptl_absorpt_process_details   sadabs

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            13918
_diffrn_reflns_av_unetI/netI     0.0658
_diffrn_reflns_av_R_equivalents  0.0626
_diffrn_reflns_limit_h_min       -28
_diffrn_reflns_limit_h_max       28
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_theta_min         1.805
_diffrn_reflns_theta_max         25.489
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 1.000
_diffrn_reflns_point_group_measured_fraction_full 1.000
_reflns_number_total             4543
_reflns_number_gt                2529
_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       'Bruker SMART'
_computing_cell_refinement       'Bruker SMART'
_computing_data_reduction        'Bruker SHELXTL'
_computing_structure_solution    'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-2013 (Sheldrick, 2013)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'

_refine_special_details          
; 
 ? 
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0912P)²+2.1228P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     SHELXL
_refine_ls_extinction_coef       0.0016(4)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         4543
_refine_ls_number_parameters     317
_refine_ls_number_restraints     70
_refine_ls_R_factor_all          0.1226
_refine_ls_R_factor_gt           0.0669
_refine_ls_wR_factor_ref         0.2100
_refine_ls_wR_factor_gt          0.1756
_refine_ls_goodness_of_fit_ref   1.029
_refine_ls_restrained_S_all      1.055
_refine_ls_shift/su_max          0.017
_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
O1 O 0.44108(8) 0.75800(16) 0.10506(9) 0.0599(5) Uani 1 1 d . . . . .
C1 C 0.40758(10) 0.7984(2) 0.15124(13) 0.0472(6) Uani 1 1 d . . . . .
C2 C 0.40131(11) 0.9188(2) 0.15944(14) 0.0510(7) Uani 1 1 d . . . . .
C3 C 0.36769(11) 0.9531(2) 0.20715(14) 0.0549(7) Uani 1 1 d . . . . .
H3 H 0.3631 1.0328 0.2138 0.066 Uiso 1 1 calc R U . . .
C4 C 0.34055(11) 0.8766(2) 0.24546(14) 0.0515(7) Uani 1 1 d . . . . .
C5 C 0.34594(11) 0.7592(2) 0.23270(14) 0.0532(7) Uani 1 1 d . . . . .
H5 H 0.3272 0.7057 0.2565 0.064 Uiso 1 1 calc R U . . .
C6 C 0.37831(10) 0.7179(2) 0.18550(13) 0.0471(6) Uani 1 1 d . . . . .
C7 C 0.37810(11) 0.5894(2) 0.17003(15) 0.0513(7) Uani 1 1 d . . . . .
C8 C 0.39889(12) 0.5166(2) 0.22437(16) 0.0557(7) Uani 1 1 d . . . . .
C9 C 0.41759(13) 0.4462(3) 0.27743(17) 0.0658(8) Uani 1 1 d . . . . .
C10 C 0.46626(16) 0.3781(3) 0.3239(2) 0.0952(12) Uani 1 1 d . . . . .
H10A H 0.4978 0.4207 0.3571 0.114 Uiso 1 1 calc R U . . .
H10B H 0.4787 0.3075 0.3036 0.114 Uiso 1 1 calc R U . . .
C11 C 0.40586(16) 0.3788(3) 0.3391(2) 0.0907(11) Uani 1 1 d . . . . .
H11A H 0.3819 0.3087 0.3278 0.109 Uiso 1 1 calc R U . . .
H11B H 0.4010 0.4219 0.3814 0.109 Uiso 1 1 calc R U . . .
C12 C 0.34857(12) 0.5460(2) 0.09573(16) 0.0566(7) Uani 1 1 d . . . . .
C13 C 0.31640(15) 0.6193(3) 0.04215(19) 0.0839(10) Uani 1 1 d . . . . .
H13 H 0.3149 0.6989 0.0514 0.101 Uiso 1 1 calc R U . . .
C14 C 0.28646(18) 0.5755(4) -0.0249(2) 0.1041(13) Uani 1 1 d . . . . .
H14 H 0.2651 0.6260 -0.0603 0.125 Uiso 1 1 calc R U . . .
C15 C 0.28785(19) 0.4595(4) -0.0398(2) 0.1020(13) Uani 1 1 d . . . . .
H15 H 0.2673 0.4304 -0.0850 0.122 Uiso 1 1 calc R U . . .
C16 C 0.3199(2) 0.3859(4) 0.0125(2) 0.1023(13) Uani 1 1 d . . . . .
H16 H 0.3213 0.3065 0.0028 0.123 Uiso 1 1 calc R U . . .
C17 C 0.35011(16) 0.4288(3) 0.07912(18) 0.0778(9) Uani 1 1 d . . . . .
H17 H 0.3721 0.3778 0.1138 0.093 Uiso 1 1 calc R U . . .
C18 C 0.49646(13) 0.7052(3) 0.14270(18) 0.0775(10) Uani 1 1 d D . . . .
H18A H 0.4889 0.6389 0.1710 0.093 Uiso 1 1 d R U . A 1
H18B H 0.5197 0.7617 0.1761 0.093 Uiso 1 1 d R U . A 1
C19 C 0.5301(5) 0.6671(12) 0.0917(6) 0.094(2) Uani 0.7 1 d D U P B 1
H19 H 0.5648 0.6260 0.1118 0.112 Uiso 0.7 1 calc R U P B 1
C20 C 0.5181(3) 0.6829(6) 0.0230(3) 0.1074(19) Uani 0.7 1 d D U P B 1
H20A H 0.4840 0.7233 -0.0003 0.129 Uiso 0.7 1 calc R U P B 1
H20B H 0.5433 0.6540 -0.0040 0.129 Uiso 0.7 1 calc R U P B 1
C19' C 0.5373(12) 0.686(3) 0.0920(14) 0.101(3) Uani 0.3 1 d D U P B 2
H19' H 0.5765 0.7086 0.0974 0.121 Uiso 0.3 1 calc R U P B 2
C20' C 0.5021(8) 0.6282(15) 0.0392(10) 0.113(3) Uani 0.3 1 d D U P B 2
H20C H 0.4635 0.6115 0.0414 0.136 Uiso 0.3 1 calc R U P B 2
H20D H 0.5155 0.6038 -0.0008 0.136 Uiso 0.3 1 calc R U P B 2
C21 C 0.42713(13) 1.0088(3) 0.11533(17) 0.0658(8) Uani 1 1 d . . . . .
C22 C 0.41122(19) 1.1349(3) 0.1331(3) 0.1076(13) Uani 1 1 d . . . . .
H22A H 0.4274 1.1893 0.1045 0.161 Uiso 1 1 calc R U . . .
H22B H 0.4275 1.1504 0.1841 0.161 Uiso 1 1 calc R U . . .
H22C H 0.3689 1.1434 0.1217 0.161 Uiso 1 1 calc R U . . .
C23 C 0.49464(15) 1.0015(3) 0.1317(2) 0.0913(11) Uani 1 1 d . . . . .
H23A H 0.5058 0.9309 0.1112 0.137 Uiso 1 1 calc R U . . .
H23B H 0.5110 1.0014 0.1836 0.137 Uiso 1 1 calc R U . . .
H23C H 0.5095 1.0677 0.1106 0.137 Uiso 1 1 calc R U . . .
C24 C 0.40018(18) 0.9892(3) 0.03412(19) 0.1001(13) Uani 1 1 d . . . . .
H24A H 0.4164 1.0448 0.0064 0.150 Uiso 1 1 calc R U . . .
H24B H 0.3580 0.9991 0.0237 0.150 Uiso 1 1 calc R U . . .
H24C H 0.4091 0.9115 0.0211 0.150 Uiso 1 1 calc R U . . .
C25 C 0.30323(13) 0.9201(3) 0.29611(16) 0.0640(8) Uani 1 1 d . . . . .
C26 C 0.3187(3) 0.8485(8) 0.3688(3) 0.088(2) Uani 0.6 1 d . U P C 1
H26A H 0.3598 0.8588 0.3927 0.132 Uiso 0.6 1 calc R U P C 1
H26B H 0.3108 0.7672 0.3582 0.132 Uiso 0.6 1 calc R U P C 1
H26C H 0.2949 0.8757 0.4003 0.132 Uiso 0.6 1 calc R U P C 1
C27 C 0.2374(3) 0.8963(7) 0.2574(4) 0.101(2) Uani 0.6 1 d . U P C 1
H27A H 0.2125 0.9259 0.2868 0.151 Uiso 0.6 1 calc R U P C 1
H27B H 0.2313 0.8137 0.2506 0.151 Uiso 0.6 1 calc R U P C 1
H27C H 0.2277 0.9346 0.2107 0.151 Uiso 0.6 1 calc R U P C 1
C28 C 0.3110(4) 1.0484(9) 0.3168(6) 0.110(3) Uani 0.6 1 d . U P C 1
H28A H 0.3523 1.0649 0.3362 0.166 Uiso 0.6 1 calc R U P C 1
H28B H 0.2898 1.0657 0.3529 0.166 Uiso 0.6 1 calc R U P C 1
H28C H 0.2959 1.0956 0.2742 0.166 Uiso 0.6 1 calc R U P C 1
C26' C 0.2857(6) 0.8303(14) 0.3409(8) 0.110(3) Uani 0.4 1 d . U P C 2
H26D H 0.2535 0.7857 0.3117 0.166 Uiso 0.4 1 calc R U P C 2
H26E H 0.2733 0.8662 0.3805 0.166 Uiso 0.4 1 calc R U P C 2
H26F H 0.3187 0.7795 0.3600 0.166 Uiso 0.4 1 calc R U P C 2
C27' C 0.2499(5) 0.9869(12) 0.2497(7) 0.116(3) Uani 0.4 1 d . U P C 2
H27D H 0.2405 0.9574 0.2007 0.174 Uiso 0.4 1 calc R U P C 2
H27E H 0.2593 1.0685 0.2494 0.174 Uiso 0.4 1 calc R U P C 2
H27F H 0.2164 0.9766 0.2701 0.174 Uiso 0.4 1 calc R U P C 2
C28' C 0.3407(7) 1.0176(15) 0.3454(9) 0.120(4) Uani 0.4 1 d . U P C 2
H28D H 0.3145 1.0742 0.3581 0.180 Uiso 0.4 1 calc R U P C 2
H28E H 0.3659 1.0553 0.3192 0.180 Uiso 0.4 1 calc R U P C 2
H28F H 0.3646 0.9828 0.3891 0.180 Uiso 0.4 1 calc R U P C 2


_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 1.387(3) . ?
O1 C18 1.442(3) . ?
C1 C6 1.397(3) . ?
C1 C2 1.399(4) . ?
C2 C3 1.390(4) . ?
C2 C21 1.539(4) . ?
C3 C4 1.385(4) . ?
C3 H3 0.9300 . ?
C4 C5 1.377(4) . ?
C4 C25 1.528(4) . ?
C5 C6 1.387(3) . ?
C5 H5 0.9300 . ?
C6 C7 1.500(4) . ?
C7 C8 1.318(4) . ?
C7 C12 1.487(4) . ?
C8 C9 1.275(4) . ?
C9 C10 1.473(4) . ?
C9 C11 1.479(4) . ?
C10 C11 1.505(5) . ?
C10 H10A 0.9700 . ?
C10 H10B 0.9700 . ?
C11 H11A 0.9700 . ?
C11 H11B 0.9700 . ?
C12 C17 1.380(4) . ?
C12 C13 1.383(4) . ?
C13 C14 1.380(5) . ?
C13 H13 0.9300 . ?
C14 C15 1.360(5) . ?
C14 H14 0.9300 . ?
C15 C16 1.371(5) . ?
C15 H15 0.9300 . ?
C16 C17 1.371(5) . ?
C16 H16 0.9300 . ?
C17 H17 0.9300 . ?
C18 C19 1.454(9) . ?
C18 C19' 1.526(19) . ?
C18 H18A 0.9700 . ?
C18 H18B 0.9700 . ?
C19 C20 1.271(12) . ?
C19 H19 0.9300 . ?
C20 H20A 0.9300 . ?
C20 H20B 0.9300 . ?
C19' C20' 1.304(19) . ?
C19' H19' 0.9300 . ?
C20' H20C 0.9300 . ?
C20' H20D 0.9300 . ?
C21 C24 1.524(5) . ?
C21 C23 1.528(4) . ?
C21 C22 1.548(5) . ?
C22 H22A 0.9600 . ?
C22 H22B 0.9600 . ?
C22 H22C 0.9600 . ?
C23 H23A 0.9600 . ?
C23 H23B 0.9600 . ?
C23 H23C 0.9600 . ?
C24 H24A 0.9600 . ?
C24 H24B 0.9600 . ?
C24 H24C 0.9600 . ?
C25 C26' 1.453(15) . ?
C25 C28 1.518(10) . ?
C25 C27' 1.535(12) . ?
C25 C27 1.551(7) . ?
C25 C26 1.563(8) . ?
C25 C28' 1.572(16) . ?
C26 H26A 0.9600 . ?
C26 H26B 0.9600 . ?
C26 H26C 0.9600 . ?
C27 H27A 0.9600 . ?
C27 H27B 0.9600 . ?
C27 H27C 0.9600 . ?
C28 H28A 0.9600 . ?
C28 H28B 0.9600 . ?
C28 H28C 0.9600 . ?
C26' H26D 0.9600 . ?
C26' H26E 0.9600 . ?
C26' H26F 0.9600 . ?
C27' H27D 0.9600 . ?
C27' H27E 0.9600 . ?
C27' H27F 0.9600 . ?
C28' H28D 0.9600 . ?
C28' H28E 0.9600 . ?
C28' H28F 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
C1 O1 C18 113.81(19) . . ?
O1 C1 C6 119.2(2) . . ?
O1 C1 C2 119.3(2) . . ?
C6 C1 C2 121.4(2) . . ?
C3 C2 C1 116.2(2) . . ?
C3 C2 C21 121.5(2) . . ?
C1 C2 C21 122.2(2) . . ?
C4 C3 C2 124.4(3) . . ?
C4 C3 H3 117.8 . . ?
C2 C3 H3 117.8 . . ?
C5 C4 C3 116.9(2) . . ?
C5 C4 C25 121.2(2) . . ?
C3 C4 C25 121.8(2) . . ?
C4 C5 C6 122.2(2) . . ?
C4 C5 H5 118.9 . . ?
C6 C5 H5 118.9 . . ?
C5 C6 C1 118.7(2) . . ?
C5 C6 C7 118.9(2) . . ?
C1 C6 C7 122.3(2) . . ?
C8 C7 C12 121.3(2) . . ?
C8 C7 C6 119.0(2) . . ?
C12 C7 C6 119.3(2) . . ?
C9 C8 C7 178.4(3) . . ?
C8 C9 C10 149.9(3) . . ?
C8 C9 C11 148.8(3) . . ?
C10 C9 C11 61.3(2) . . ?
C9 C10 C11 59.6(2) . . ?
C9 C10 H10A 117.8 . . ?
C11 C10 H10A 117.8 . . ?
C9 C10 H10B 117.8 . . ?
C11 C10 H10B 117.8 . . ?
H10A C10 H10B 115.0 . . ?
C9 C11 C10 59.2(2) . . ?
C9 C11 H11A 117.9 . . ?
C10 C11 H11A 117.9 . . ?
C9 C11 H11B 117.9 . . ?
C10 C11 H11B 117.9 . . ?
H11A C11 H11B 115.0 . . ?
C17 C12 C13 117.6(3) . . ?
C17 C12 C7 120.5(3) . . ?
C13 C12 C7 121.9(3) . . ?
C14 C13 C12 120.7(3) . . ?
C14 C13 H13 119.6 . . ?
C12 C13 H13 119.6 . . ?
C15 C14 C13 120.8(4) . . ?
C15 C14 H14 119.6 . . ?
C13 C14 H14 119.6 . . ?
C14 C15 C16 119.1(4) . . ?
C14 C15 H15 120.4 . . ?
C16 C15 H15 120.4 . . ?
C17 C16 C15 120.4(4) . . ?
C17 C16 H16 119.8 . . ?
C15 C16 H16 119.8 . . ?
C16 C17 C12 121.3(3) . . ?
C16 C17 H17 119.3 . . ?
C12 C17 H17 119.3 . . ?
O1 C18 C19 111.3(6) . . ?
O1 C18 C19' 111.9(14) . . ?
O1 C18 H18A 109.7 . . ?
C19 C18 H18A 109.5 . . ?
O1 C18 H18B 109.1 . . ?
C19 C18 H18B 109.1 . . ?
H18A C18 H18B 108.1 . . ?
C20 C19 C18 128.0(12) . . ?
C20 C19 H19 116.0 . . ?
C18 C19 H19 116.0 . . ?
C19 C20 H20A 120.0 . . ?
C19 C20 H20B 120.0 . . ?
H20A C20 H20B 120.0 . . ?
C20' C19' C18 100.5(17) . . ?
C20' C19' H19' 129.7 . . ?
C18 C19' H19' 129.7 . . ?
C19' C20' H20C 120.0 . . ?
C19' C20' H20D 120.0 . . ?
H20C C20' H20D 120.0 . . ?
C24 C21 C23 110.0(3) . . ?
C24 C21 C2 109.2(2) . . ?
C23 C21 C2 112.1(2) . . ?
C24 C21 C22 107.1(3) . . ?
C23 C21 C22 107.3(3) . . ?
C2 C21 C22 111.1(3) . . ?
C21 C22 H22A 109.5 . . ?
C21 C22 H22B 109.5 . . ?
H22A C22 H22B 109.5 . . ?
C21 C22 H22C 109.5 . . ?
H22A C22 H22C 109.5 . . ?
H22B C22 H22C 109.5 . . ?
C21 C23 H23A 109.5 . . ?
C21 C23 H23B 109.5 . . ?
H23A C23 H23B 109.5 . . ?
C21 C23 H23C 109.5 . . ?
H23A C23 H23C 109.5 . . ?
H23B C23 H23C 109.5 . . ?
C21 C24 H24A 109.5 . . ?
C21 C24 H24B 109.5 . . ?
H24A C24 H24B 109.5 . . ?
C21 C24 H24C 109.5 . . ?
H24A C24 H24C 109.5 . . ?
H24B C24 H24C 109.5 . . ?
C26' C25 C4 114.9(6) . . ?
C28 C25 C4 115.2(5) . . ?
C26' C25 C27' 112.3(8) . . ?
C4 C25 C27' 108.1(5) . . ?
C28 C25 C27 109.4(5) . . ?
C4 C25 C27 107.3(3) . . ?
C28 C25 C26 107.1(5) . . ?
C4 C25 C26 109.8(3) . . ?
C27 C25 C26 107.9(5) . . ?
C26' C25 C28' 110.6(9) . . ?
C4 C25 C28' 106.5(6) . . ?
C27' C25 C28' 103.7(8) . . ?
C25 C26 H26A 109.5 . . ?
C25 C26 H26B 109.5 . . ?
H26A C26 H26B 109.5 . . ?
C25 C26 H26C 109.5 . . ?
H26A C26 H26C 109.5 . . ?
H26B C26 H26C 109.5 . . ?
C25 C27 H27A 109.5 . . ?
C25 C27 H27B 109.5 . . ?
H27A C27 H27B 109.5 . . ?
C25 C27 H27C 109.5 . . ?
H27A C27 H27C 109.5 . . ?
H27B C27 H27C 109.5 . . ?
C25 C28 H28A 109.5 . . ?
C25 C28 H28B 109.5 . . ?
H28A C28 H28B 109.5 . . ?
C25 C28 H28C 109.5 . . ?
H28A C28 H28C 109.5 . . ?
H28B C28 H28C 109.5 . . ?
C25 C26' H26D 109.5 . . ?
C25 C26' H26E 109.5 . . ?
H26D C26' H26E 109.5 . . ?
C25 C26' H26F 109.5 . . ?
H26D C26' H26F 109.5 . . ?
H26E C26' H26F 109.5 . . ?
C25 C27' H27D 109.5 . . ?
C25 C27' H27E 109.5 . . ?
H27D C27' H27E 109.5 . . ?
C25 C27' H27F 109.5 . . ?
H27D C27' H27F 109.5 . . ?
H27E C27' H27F 109.5 . . ?
C25 C28' H28D 109.5 . . ?
C25 C28' H28E 109.5 . . ?
H28D C28' H28E 109.5 . . ?
C25 C28' H28F 109.5 . . ?
H28D C28' H28F 109.5 . . ?
H28E C28' H28F 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
C18 O1 C1 C6 -73.9(3) . . . . ?
C18 O1 C1 C2 109.5(3) . . . . ?
O1 C1 C2 C3 -179.3(2) . . . . ?
C6 C1 C2 C3 4.1(4) . . . . ?
O1 C1 C2 C21 3.9(4) . . . . ?
C6 C1 C2 C21 -172.7(2) . . . . ?
C1 C2 C3 C4 -0.5(4) . . . . ?
C21 C2 C3 C4 176.4(2) . . . . ?
C2 C3 C4 C5 -2.5(4) . . . . ?
C2 C3 C4 C25 -178.9(2) . . . . ?
C3 C4 C5 C6 1.8(4) . . . . ?
C25 C4 C5 C6 178.3(2) . . . . ?
C4 C5 C6 C1 1.6(4) . . . . ?
C4 C5 C6 C7 -175.2(2) . . . . ?
O1 C1 C6 C5 178.7(2) . . . . ?
C2 C1 C6 C5 -4.7(4) . . . . ?
O1 C1 C6 C7 -4.5(4) . . . . ?
C2 C1 C6 C7 172.0(2) . . . . ?
C5 C6 C7 C8 -61.3(3) . . . . ?
C1 C6 C7 C8 122.0(3) . . . . ?
C5 C6 C7 C12 112.1(3) . . . . ?
C1 C6 C7 C12 -64.7(3) . . . . ?
C8 C9 C10 C11 177.0(6) . . . . ?
C8 C9 C11 C10 -177.1(6) . . . . ?
C8 C7 C12 C17 -9.8(4) . . . . ?
C6 C7 C12 C17 177.0(3) . . . . ?
C8 C7 C12 C13 167.0(3) . . . . ?
C6 C7 C12 C13 -6.2(4) . . . . ?
C17 C12 C13 C14 0.9(5) . . . . ?
C7 C12 C13 C14 -176.0(3) . . . . ?
C12 C13 C14 C15 0.0(6) . . . . ?
C13 C14 C15 C16 -0.6(7) . . . . ?
C14 C15 C16 C17 0.2(7) . . . . ?
C15 C16 C17 C12 0.8(6) . . . . ?
C13 C12 C17 C16 -1.3(5) . . . . ?
C7 C12 C17 C16 175.7(3) . . . . ?
C1 O1 C18 C19 -178.7(5) . . . . ?
C1 O1 C18 C19' -167.9(13) . . . . ?
O1 C18 C19 C20 5.4(13) . . . . ?
C19' C18 C19 C20 -90(12) . . . . ?
O1 C18 C19' C20' -53(3) . . . . ?
C19 C18 C19' C20' 36(9) . . . . ?
C3 C2 C21 C24 -117.0(3) . . . . ?
C1 C2 C21 C24 59.6(4) . . . . ?
C3 C2 C21 C23 120.9(3) . . . . ?
C1 C2 C21 C23 -62.5(4) . . . . ?
C3 C2 C21 C22 0.9(4) . . . . ?
C1 C2 C21 C22 177.6(3) . . . . ?
C5 C4 C25 C26' 13.0(7) . . . . ?
C3 C4 C25 C26' -170.7(7) . . . . ?
C5 C4 C25 C28 168.4(5) . . . . ?
C3 C4 C25 C28 -15.3(5) . . . . ?
C5 C4 C25 C27' -113.3(7) . . . . ?
C3 C4 C25 C27' 63.0(7) . . . . ?
C5 C4 C25 C27 -69.5(5) . . . . ?
C3 C4 C25 C27 106.8(4) . . . . ?
C5 C4 C25 C26 47.5(5) . . . . ?
C3 C4 C25 C26 -136.2(4) . . . . ?
C5 C4 C25 C28' 135.8(7) . . . . ?
C3 C4 C25 C28' -47.9(7) . . . . ?

_refine_diff_density_max         0.420
_refine_diff_density_min         -0.239
_refine_diff_density_rms         0.036

_shelxl_version_number           2013-4



####################################################################### 
# 
# 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_214
_database_code_depnum_ccdc_archive 'CCDC 997410'
_audit_update_record             
;
2014-04-15 deposited with the CCDC.
2015-06-23 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C20 H16 Br2 O'
_chemical_formula_sum            'C20 H16 Br2 O'
_chemical_formula_weight         432.15


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'
Br Br -0.6763 1.2805 '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                   6.06980(10)
_cell_length_b                   11.45890(10)
_cell_length_c                   13.8421(3)
_cell_angle_alpha                67.0270(10)
_cell_angle_beta                 85.3480(10)
_cell_angle_gamma                76.3370(10)
_cell_volume                     861.26(2)
_cell_formula_units_Z            2
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    4140
_cell_measurement_theta_min      3.47
_cell_measurement_theta_max      66.61

_exptl_crystal_description       prismatic
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.25
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.12
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.666
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             428
_exptl_absorpt_coefficient_mu    5.971
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.4926
_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            5017
_diffrn_reflns_av_R_equivalents  0.0199
_diffrn_reflns_av_sigmaI/netI    0.0278
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_theta_min         3.47
_diffrn_reflns_theta_max         66.95
_reflns_number_total             2759
_reflns_number_gt                2649
_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)+(0.0551P)²+0.7482P] 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     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         2759
_refine_ls_number_parameters     208
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0373
_refine_ls_R_factor_gt           0.0364
_refine_ls_wR_factor_ref         0.1015
_refine_ls_wR_factor_gt          0.1006
_refine_ls_goodness_of_fit_ref   1.058
_refine_ls_restrained_S_all      1.058
_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
Br1 Br -0.19319(7) 0.01024(4) 1.13335(3) 0.06232(16) Uani 1 1 d . . .
Br2 Br 0.22526(7) 0.08826(5) 0.53100(4) 0.07576(18) Uani 1 1 d . . .
O1 O -0.9288(4) 0.3979(2) 0.83271(17) 0.0508(5) Uani 1 1 d . . .
C1 C -0.4747(5) 0.3764(3) 0.7573(2) 0.0396(6) Uani 1 1 d . . .
C2 C -0.5558(6) 0.5039(3) 0.7145(2) 0.0469(7) Uani 1 1 d . . .
C3 C -0.6857(6) 0.6062(3) 0.7529(3) 0.0520(8) Uani 1 1 d . . .
C4 C -0.9054(6) 0.6174(4) 0.8114(3) 0.0568(8) Uani 1 1 d . . .
H4A H -0.9998 0.7059 0.7869 0.068 Uiso 1 1 calc R . .
C5 C -1.0409(6) 0.5138(4) 0.8484(3) 0.0572(8) Uani 1 1 d . . .
H5A H -1.0715 0.4920 0.9225 0.069 Uiso 1 1 calc R . .
H5B H -1.1854 0.5482 0.8112 0.069 Uiso 1 1 calc R . .
C6 C -0.7570(5) 0.3154(3) 0.9019(2) 0.0411(6) Uani 1 1 d . . .
C7 C -0.8084(6) 0.2440(3) 1.0045(3) 0.0515(8) Uani 1 1 d . . .
H7A H -0.9573 0.2575 1.0271 0.062 Uiso 1 1 calc R . .
C8 C -0.6414(6) 0.1533(3) 1.0733(2) 0.0507(8) Uani 1 1 d . . .
H8A H -0.6759 0.1062 1.1423 0.061 Uiso 1 1 calc R . .
C9 C -0.4230(5) 0.1340(3) 1.0379(2) 0.0428(6) Uani 1 1 d . . .
C10 C -0.3672(5) 0.2026(3) 0.9351(2) 0.0390(6) Uani 1 1 d . . .
H10A H -0.2188 0.1856 0.9126 0.047 Uiso 1 1 calc R . .
C11 C -0.5343(5) 0.2972(3) 0.8655(2) 0.0374(6) Uani 1 1 d . . .
C12 C -0.5231(8) 0.6089(4) 0.6084(3) 0.0763(13) Uani 1 1 d . . .
H12A H -0.6089 0.6105 0.5516 0.092 Uiso 1 1 calc R . .
H12B H -0.3654 0.6078 0.5896 0.092 Uiso 1 1 calc R . .
C13 C -0.6330(8) 0.7136(4) 0.6516(3) 0.0790(13) Uani 1 1 d . . .
H13A H -0.5277 0.7600 0.6614 0.095 Uiso 1 1 calc R . .
H13B H -0.7668 0.7735 0.6127 0.095 Uiso 1 1 calc R . .
C14 C -0.6882(6) 0.6044(4) 0.8622(3) 0.0563(8) Uani 1 1 d . . .
H14A H -0.6269 0.5223 0.9186 0.068 Uiso 1 1 calc R . .
H14B H -0.6625 0.6806 0.8703 0.068 Uiso 1 1 calc R . .
C15 C -0.3098(5) 0.3077(3) 0.7001(2) 0.0384(6) Uani 1 1 d . . .
C16 C -0.1177(5) 0.3531(3) 0.6551(2) 0.0451(7) Uani 1 1 d . . .
H16A H -0.0947 0.4285 0.6591 0.054 Uiso 1 1 calc R . .
C17 C 0.0401(5) 0.2885(3) 0.6043(2) 0.0481(7) Uani 1 1 d . . .
H17A H 0.1684 0.3195 0.5750 0.058 Uiso 1 1 calc R . .
C18 C 0.0036(5) 0.1777(3) 0.5982(2) 0.0466(7) Uani 1 1 d . . .
C19 C -0.1855(6) 0.1301(3) 0.6411(2) 0.0482(7) Uani 1 1 d . . .
H19A H -0.2089 0.0556 0.6355 0.058 Uiso 1 1 calc R . .
C20 C -0.3400(5) 0.1951(3) 0.6925(2) 0.0448(7) Uani 1 1 d . . .
H20A H -0.4666 0.1626 0.7227 0.054 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
Br1 C9 1.898(3) . ?
Br2 C18 1.901(3) . ?
O1 C6 1.374(4) . ?
O1 C5 1.431(4) . ?
C1 C2 1.327(4) . ?
C1 C11 1.485(4) . ?
C1 C15 1.495(4) . ?
C2 C3 1.504(4) . ?
C2 C12 1.526(4) . ?
C3 C14 1.503(5) . ?
C3 C4 1.508(5) . ?
C3 C13 1.533(5) . ?
C4 C14 1.494(5) . ?
C4 C5 1.506(6) . ?
C4 H4A 0.9800 . ?
C5 H5A 0.9700 . ?
C5 H5B 0.9700 . ?
C6 C7 1.388(4) . ?
C6 C11 1.400(4) . ?
C7 C8 1.379(5) . ?
C7 H7A 0.9300 . ?
C8 C9 1.374(5) . ?
C8 H8A 0.9300 . ?
C9 C10 1.390(4) . ?
C10 C11 1.399(4) . ?
C10 H10A 0.9300 . ?
C12 C13 1.536(6) . ?
C12 H12A 0.9700 . ?
C12 H12B 0.9700 . ?
C13 H13A 0.9700 . ?
C13 H13B 0.9700 . ?
C14 H14A 0.9700 . ?
C14 H14B 0.9700 . ?
C15 C20 1.389(4) . ?
C15 C16 1.391(4) . ?
C16 C17 1.386(4) . ?
C16 H16A 0.9300 . ?
C17 C18 1.375(5) . ?
C17 H17A 0.9300 . ?
C18 C19 1.378(5) . ?
C19 C20 1.385(4) . ?
C19 H19A 0.9300 . ?
C20 H20A 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
C6 O1 C5 117.2(2) . . ?
C2 C1 C11 121.6(3) . . ?
C2 C1 C15 121.0(3) . . ?
C11 C1 C15 117.3(3) . . ?
C1 C2 C3 135.6(3) . . ?
C1 C2 C12 133.4(3) . . ?
C3 C2 C12 90.4(3) . . ?
C14 C3 C2 127.7(3) . . ?
C14 C3 C4 59.5(2) . . ?
C2 C3 C4 132.3(3) . . ?
C14 C3 C13 126.7(3) . . ?
C2 C3 C13 90.5(3) . . ?
C4 C3 C13 123.9(3) . . ?
C14 C4 C5 123.4(3) . . ?
C14 C4 C3 60.1(2) . . ?
C5 C4 C3 123.3(3) . . ?
C14 C4 H4A 113.3 . . ?
C5 C4 H4A 113.3 . . ?
C3 C4 H4A 113.3 . . ?
O1 C5 C4 113.3(3) . . ?
O1 C5 H5A 108.9 . . ?
C4 C5 H5A 108.9 . . ?
O1 C5 H5B 108.9 . . ?
C4 C5 H5B 108.9 . . ?
H5A C5 H5B 107.7 . . ?
O1 C6 C7 119.6(3) . . ?
O1 C6 C11 119.3(3) . . ?
C7 C6 C11 120.9(3) . . ?
C8 C7 C6 120.8(3) . . ?
C8 C7 H7A 119.6 . . ?
C6 C7 H7A 119.6 . . ?
C9 C8 C7 118.6(3) . . ?
C9 C8 H8A 120.7 . . ?
C7 C8 H8A 120.7 . . ?
C8 C9 C10 121.8(3) . . ?
C8 C9 Br1 118.4(2) . . ?
C10 C9 Br1 119.7(2) . . ?
C9 C10 C11 119.9(3) . . ?
C9 C10 H10A 120.0 . . ?
C11 C10 H10A 120.0 . . ?
C10 C11 C6 117.9(3) . . ?
C10 C11 C1 120.5(3) . . ?
C6 C11 C1 121.6(3) . . ?
C2 C12 C13 89.5(3) . . ?
C2 C12 H12A 113.7 . . ?
C13 C12 H12A 113.7 . . ?
C2 C12 H12B 113.7 . . ?
C13 C12 H12B 113.7 . . ?
H12A C12 H12B 111.0 . . ?
C3 C13 C12 89.0(3) . . ?
C3 C13 H13A 113.8 . . ?
C12 C13 H13A 113.8 . . ?
C3 C13 H13B 113.8 . . ?
C12 C13 H13B 113.8 . . ?
H13A C13 H13B 111.0 . . ?
C4 C14 C3 60.4(2) . . ?
C4 C14 H14A 117.7 . . ?
C3 C14 H14A 117.7 . . ?
C4 C14 H14B 117.7 . . ?
C3 C14 H14B 117.7 . . ?
H14A C14 H14B 114.8 . . ?
C20 C15 C16 118.0(3) . . ?
C20 C15 C1 121.3(3) . . ?
C16 C15 C1 120.7(3) . . ?
C17 C16 C15 121.4(3) . . ?
C17 C16 H16A 119.3 . . ?
C15 C16 H16A 119.3 . . ?
C18 C17 C16 118.8(3) . . ?
C18 C17 H17A 120.6 . . ?
C16 C17 H17A 120.6 . . ?
C17 C18 C19 121.5(3) . . ?
C17 C18 Br2 118.2(2) . . ?
C19 C18 Br2 120.3(2) . . ?
C18 C19 C20 118.9(3) . . ?
C18 C19 H19A 120.5 . . ?
C20 C19 H19A 120.5 . . ?
C19 C20 C15 121.4(3) . . ?
C19 C20 H20A 119.3 . . ?
C15 C20 H20A 119.3 . . ?

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 C1 C2 C3 9.7(6) . . . . ?
C15 C1 C2 C3 -167.1(4) . . . . ?
C11 C1 C2 C12 178.8(4) . . . . ?
C15 C1 C2 C12 2.0(6) . . . . ?
C1 C2 C3 C14 26.6(7) . . . . ?
C12 C2 C3 C14 -145.5(4) . . . . ?
C1 C2 C3 C4 -53.9(7) . . . . ?
C12 C2 C3 C4 134.0(4) . . . . ?
C1 C2 C3 C13 166.4(5) . . . . ?
C12 C2 C3 C13 -5.7(4) . . . . ?
C2 C3 C4 C14 115.1(4) . . . . ?
C13 C3 C4 C14 -116.1(4) . . . . ?
C14 C3 C4 C5 -112.4(4) . . . . ?
C2 C3 C4 C5 2.7(6) . . . . ?
C13 C3 C4 C5 131.5(4) . . . . ?
C6 O1 C5 C4 77.0(4) . . . . ?
C14 C4 C5 O1 -67.3(4) . . . . ?
C3 C4 C5 O1 6.4(5) . . . . ?
C5 O1 C6 C7 71.0(4) . . . . ?
C5 O1 C6 C11 -113.8(3) . . . . ?
O1 C6 C7 C8 175.1(3) . . . . ?
C11 C6 C7 C8 -0.1(5) . . . . ?
C6 C7 C8 C9 -0.6(5) . . . . ?
C7 C8 C9 C10 -0.4(5) . . . . ?
C7 C8 C9 Br1 179.4(2) . . . . ?
C8 C9 C10 C11 2.1(5) . . . . ?
Br1 C9 C10 C11 -177.7(2) . . . . ?
C9 C10 C11 C6 -2.7(4) . . . . ?
C9 C10 C11 C1 176.6(3) . . . . ?
O1 C6 C11 C10 -173.5(2) . . . . ?
C7 C6 C11 C10 1.7(4) . . . . ?
O1 C6 C11 C1 7.3(4) . . . . ?
C7 C6 C11 C1 -177.5(3) . . . . ?
C2 C1 C11 C10 -135.5(3) . . . . ?
C15 C1 C11 C10 41.5(4) . . . . ?
C2 C1 C11 C6 43.7(4) . . . . ?
C15 C1 C11 C6 -139.3(3) . . . . ?
C1 C2 C12 C13 -166.7(4) . . . . ?
C3 C2 C12 C13 5.7(4) . . . . ?
C14 C3 C13 C12 146.1(4) . . . . ?
C2 C3 C13 C12 5.7(3) . . . . ?
C4 C3 C13 C12 -139.1(4) . . . . ?
C2 C12 C13 C3 -5.6(3) . . . . ?
C5 C4 C14 C3 112.4(4) . . . . ?
C2 C3 C14 C4 -122.2(4) . . . . ?
C13 C3 C14 C4 111.6(4) . . . . ?
C2 C1 C15 C20 -131.9(3) . . . . ?
C11 C1 C15 C20 51.1(4) . . . . ?
C2 C1 C15 C16 49.8(4) . . . . ?
C11 C1 C15 C16 -127.2(3) . . . . ?
C20 C15 C16 C17 -0.2(5) . . . . ?
C1 C15 C16 C17 178.1(3) . . . . ?
C15 C16 C17 C18 0.5(5) . . . . ?
C16 C17 C18 C19 0.0(5) . . . . ?
C16 C17 C18 Br2 -178.6(2) . . . . ?
C17 C18 C19 C20 -0.8(5) . . . . ?
Br2 C18 C19 C20 177.9(2) . . . . ?
C18 C19 C20 C15 1.1(5) . . . . ?
C16 C15 C20 C19 -0.6(5) . . . . ?
C1 C15 C20 C19 -178.9(3) . . . . ?

_diffrn_measured_fraction_theta_max 0.901
_diffrn_reflns_theta_full        66.95
_diffrn_measured_fraction_theta_full 0.901
_refine_diff_density_max         0.452
_refine_diff_density_min         -0.522
_refine_diff_density_rms         0.075
