# 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. 
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data_mo_CV438_0m
_database_code_depnum_ccdc_archive 'CCDC 1046068'
_audit_update_record             
;
2015-01-28 deposited with the CCDC.
2015-04-27 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C28 H27 Br O4'
_chemical_formula_weight         507.40
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'
Br Br -0.2901 2.4595 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           Orthorhombic
_space_group_IT_number           19
_symmetry_space_group_name_H-M   P2(1)2(1)2(1)
_space_group_name_Hall           'P 2ac 2ab'

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

_cell_length_a                   8.7857(6)
_cell_length_b                   16.2342(7)
_cell_length_c                   17.0357(10)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     2429.8(2)
_cell_formula_units_Z            4
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    4597
_cell_measurement_theta_min      2.61
_cell_measurement_theta_max      30.04

_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.387
_exptl_crystal_F_000             1048
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.15
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.10
_exptl_absorpt_coefficient_mu    1.723
_shelx_estimated_absorpt_T_min   0.782
_shelx_estimated_absorpt_T_max   0.847
_exptl_absorpt_correction_type   empirical
_exptl_absorpt_correction_T_min  0.788
_exptl_absorpt_correction_T_max  0.847
_exptl_absorpt_process_details   
; 
 SADABS Version 2008/1 Bruker-Nonius
 Blessing, Acta Cryst. (1995) A51 33-38
;
_exptl_special_details           
; 
 It should be noted that the esd's of the cell dimensions are probably too low;
 they should be multiplied by a factor of 2 to 10
;
_diffrn_ambient_temperature      100(2)
_diffrn_measurement_specimen_support 'magnetic support with MicroMount'
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'Microfocus source E025 IuS'
_diffrn_source_type              'Bruker APEX DUO'
_diffrn_source_power             50
_diffrn_source_current           0.6
_diffrn_source_size              '0.2 mm x 0.2 mm fine focus'
_diffrn_radiation_monochromator  'Quazar MX Multilayer Optics'
_diffrn_detector_type            '4K CCD area detector APEX II'
_diffrn_measurement_device_type  'APEX DUO Kappa 4-axis goniometer'
_diffrn_measurement_method       
;
 Fullsphere data collection, phi and omega scans
;
_diffrn_detector_area_resol_mean 512
_diffrn_reflns_number            14745
_diffrn_reflns_av_unetI/netI     0.0507
_diffrn_reflns_av_R_equivalents  0.0289
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_k_min       -22
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_limit_l_max       25
_diffrn_reflns_theta_min         1.733
_diffrn_reflns_theta_max         32.555
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.865
_diffrn_measured_fraction_theta_full 0.988
_diffrn_reflns_Laue_measured_fraction_max 0.865
_diffrn_reflns_Laue_measured_fraction_full 0.988
_diffrn_reflns_point_group_measured_fraction_max 0.829
_diffrn_reflns_point_group_measured_fraction_full 0.981
_reflns_number_total             7325
_reflns_number_gt                6317
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.723
_reflns_Friedel_fraction_max     0.784
_reflns_Friedel_fraction_full    0.972

_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 APEX2 v2011.4-0'
_computing_cell_refinement       'Bruker APEX2 v2011.4-0'
_computing_data_reduction        'Bruker SAINT V7.60A'
_computing_structure_solution    Sir2011
_computing_structure_refinement  'SHELXL-2014 (Sheldrick, 2014)'
_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)+(0.0335P)²+0.0062P] 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_abs_structure_details 
;
 Flack x determined using 2425 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_chemical_absolute_configuration ad
_refine_ls_abs_structure_Flack   -0.007(4)
_refine_ls_number_reflns         7325
_refine_ls_number_parameters     316
_refine_ls_number_restraints     56
_refine_ls_R_factor_all          0.0456
_refine_ls_R_factor_gt           0.0345
_refine_ls_wR_factor_ref         0.0727
_refine_ls_wR_factor_gt          0.0694
_refine_ls_goodness_of_fit_ref   1.037
_refine_ls_restrained_S_all      1.037
_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
Br1 Br 0.08017(3) 1.11282(2) -0.27006(2) 0.01988(7) Uani 1 1 d . . . . .
O1 O 0.6579(2) 0.69974(11) 0.07712(10) 0.0175(4) Uani 1 1 d . . . . .
O2 O 0.6817(2) 1.04113(12) -0.14486(11) 0.0200(4) Uani 1 1 d . . . . .
O3 O 0.6462(2) 1.08465(12) 0.05206(13) 0.0238(5) Uani 1 1 d D . . . .
O4 O 0.8416(2) 0.99724(13) 0.03177(13) 0.0242(5) Uani 1 1 d . . . . .
C1 C 0.7231(3) 0.72599(17) 0.21247(14) 0.0174(6) Uani 1 1 d . . . . .
C2 C 0.7063(4) 0.64209(16) 0.22951(17) 0.0227(6) Uani 1 1 d . . . . .
H2 H 0.6745 0.6049 0.1897 0.027 Uiso 1 1 calc R U . . .
C3 C 0.7363(4) 0.6135(2) 0.30491(16) 0.0269(7) Uani 1 1 d . . . . .
H3 H 0.7242 0.5566 0.3164 0.032 Uiso 1 1 calc R U . . .
C4 C 0.7835(4) 0.66658(19) 0.36315(16) 0.0251(7) Uani 1 1 d . . . . .
H4 H 0.8035 0.6465 0.4145 0.030 Uiso 1 1 calc R U . . .
C5 C 0.8016(4) 0.74971(19) 0.34621(16) 0.0231(7) Uani 1 1 d . . . . .
H5 H 0.8343 0.7865 0.3861 0.028 Uiso 1 1 calc R U . . .
C6 C 0.7722(3) 0.77913(16) 0.27155(16) 0.0188(5) Uani 1 1 d . . . . .
H6 H 0.7856 0.8360 0.2604 0.023 Uiso 1 1 calc R U . . .
C7 C 0.6945(3) 0.75731(17) 0.13362(15) 0.0156(6) Uani 1 1 d . . . . .
C8 C 0.7014(3) 0.83349(16) 0.10066(14) 0.0137(5) Uani 1 1 d . . . . .
H8 H 0.7236 0.8837 0.1270 0.016 Uiso 1 1 calc R U . . .
C9 C 0.6687(3) 0.82383(17) 0.01843(14) 0.0146(5) Uani 1 1 d . . . . .
C10 C 0.6433(3) 0.74237(18) 0.00726(15) 0.0160(6) Uani 1 1 d . . . . .
C11 C 0.6044(4) 0.69693(17) -0.06589(14) 0.0185(6) Uani 1 1 d . . . . .
H11A H 0.4971 0.6785 -0.0643 0.022 Uiso 1 1 calc R U . . .
H11B H 0.6705 0.6479 -0.0716 0.022 Uiso 1 1 calc R U . . .
C12 C 0.6293(4) 0.75636(18) -0.13485(16) 0.0205(6) Uani 1 1 d . . . . .
H12A H 0.7393 0.7594 -0.1471 0.025 Uiso 1 1 calc R U . . .
H12B H 0.5760 0.7350 -0.1818 0.025 Uiso 1 1 calc R U . . .
C13 C 0.5701(4) 0.84290(16) -0.11594(13) 0.0186(6) Uani 1 1 d . . . . .
H13A H 0.4618 0.8394 -0.1002 0.022 Uiso 1 1 calc R U . . .
H13B H 0.5763 0.8776 -0.1636 0.022 Uiso 1 1 calc R U . . .
C14 C 0.6619(3) 0.88357(17) -0.04955(13) 0.0141(5) Uani 1 1 d . . . . .
H14 H 0.7681 0.8923 -0.0690 0.017 Uiso 1 1 calc R U . . .
C15 C 0.5962(3) 0.96868(15) -0.02615(13) 0.0124(5) Uani 1 1 d . . . . .
C16 C 0.5772(4) 1.01942(15) -0.10336(13) 0.0140(5) Uani 1 1 d . . . . .
C17 C 0.4131(4) 1.03355(15) -0.11576(13) 0.0130(5) Uani 1 1 d . . . . .
C18 C 0.3421(3) 1.06852(16) -0.18150(15) 0.0150(5) Uani 1 1 d . . . . .
H18 H 0.3994 1.0890 -0.2246 0.018 Uiso 1 1 calc R U . . .
C19 C 0.1852(3) 1.07188(16) -0.18080(15) 0.0154(5) Uani 1 1 d . . . . .
C20 C 0.0996(3) 1.04428(16) -0.11669(15) 0.0163(6) Uani 1 1 d . . . . .
H20 H -0.0082 1.0489 -0.1174 0.020 Uiso 1 1 calc R U . . .
C21 C 0.1727(3) 1.00989(16) -0.05149(15) 0.0149(5) Uani 1 1 d . . . . .
H21 H 0.1155 0.9913 -0.0076 0.018 Uiso 1 1 calc R U . . .
C22 C 0.3313(3) 1.00335(16) -0.05211(14) 0.0118(5) Uani 1 1 d . . . . .
C23 C 0.4334(3) 0.96472(16) 0.00870(13) 0.0135(5) Uani 1 1 d . . . . .
H23A H 0.4032 0.9069 0.0186 0.016 Uiso 1 1 calc R U . . .
H23B H 0.4281 0.9957 0.0587 0.016 Uiso 1 1 calc R U . . .
C24 C 0.7109(3) 1.01653(17) 0.02316(15) 0.0148(5) Uani 1 1 d . . . . .
C25 C 0.735(2) 1.1494(5) 0.0932(7) 0.0277(10) Uani 0.6 1 d D U P A 1
C26 C 0.7856(15) 1.1138(7) 0.1721(6) 0.0344(17) Uani 0.6 1 d D U P A 1
H26A H 0.6961 1.0951 0.2015 0.052 Uiso 0.6 1 calc R U P A 1
H26B H 0.8388 1.1563 0.2023 0.052 Uiso 0.6 1 calc R U P A 1
H26C H 0.8541 1.0671 0.1631 0.052 Uiso 0.6 1 calc R U P A 1
C27 C 0.8655(11) 1.1770(6) 0.0408(7) 0.0310(13) Uani 0.6 1 d D U P A 1
H27A H 0.9403 1.1325 0.0363 0.046 Uiso 0.6 1 calc R U P A 1
H27B H 0.9143 1.2257 0.0638 0.046 Uiso 0.6 1 calc R U P A 1
H27C H 0.8262 1.1908 -0.0114 0.046 Uiso 0.6 1 calc R U P A 1
C28 C 0.6224(8) 1.2186(4) 0.1040(4) 0.0346(13) Uani 0.6 1 d D U P A 1
H28A H 0.5944 1.2411 0.0526 0.052 Uiso 0.6 1 calc R U P A 1
H28B H 0.6686 1.2620 0.1361 0.052 Uiso 0.6 1 calc R U P A 1
H28C H 0.5312 1.1976 0.1304 0.052 Uiso 0.6 1 calc R U P A 1
C25' C 0.739(3) 1.1413(7) 0.1024(10) 0.0277(10) Uani 0.4 1 d D U P A 2
C26' C 0.818(2) 1.0952(12) 0.1692(10) 0.0344(17) Uani 0.4 1 d D U P A 2
H26D H 0.7418 1.0691 0.2029 0.052 Uiso 0.4 1 calc R U P A 2
H26E H 0.8786 1.1341 0.2003 0.052 Uiso 0.4 1 calc R U P A 2
H26F H 0.8854 1.0528 0.1472 0.052 Uiso 0.4 1 calc R U P A 2
C27' C 0.6198(12) 1.2019(6) 0.1320(6) 0.0310(13) Uani 0.4 1 d D U P A 2
H27D H 0.5599 1.2225 0.0876 0.046 Uiso 0.4 1 calc R U P A 2
H27E H 0.6705 1.2482 0.1581 0.046 Uiso 0.4 1 calc R U P A 2
H27F H 0.5523 1.1741 0.1693 0.046 Uiso 0.4 1 calc R U P A 2
C28' C 0.8507(16) 1.1864(10) 0.0506(11) 0.0346(13) Uani 0.4 1 d D U P A 2
H28D H 0.9183 1.1465 0.0251 0.052 Uiso 0.4 1 calc R U P A 2
H28E H 0.9113 1.2244 0.0826 0.052 Uiso 0.4 1 calc R U P A 2
H28F H 0.7952 1.2175 0.0104 0.052 Uiso 0.4 1 calc R U P A 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
Br1 C19 1.899(3) . ?
O1 C7 1.380(3) . ?
O1 C10 1.383(3) . ?
O2 C16 1.211(3) . ?
O3 C24 1.337(3) . ?
O3 C25 1.485(7) . ?
O3 C25' 1.497(10) . ?
O4 C24 1.200(4) . ?
C1 C6 1.394(4) . ?
C1 C2 1.400(4) . ?
C1 C7 1.458(4) . ?
C2 C3 1.391(4) . ?
C3 C4 1.378(4) . ?
C4 C5 1.389(4) . ?
C5 C6 1.383(4) . ?
C7 C8 1.360(4) . ?
C8 C9 1.439(3) . ?
C9 C10 1.355(4) . ?
C9 C14 1.512(3) . ?
C10 C11 1.488(4) . ?
C11 C12 1.536(4) . ?
C12 C13 1.532(4) . ?
C13 C14 1.538(4) . ?
C14 C15 1.550(4) . ?
C15 C24 1.525(4) . ?
C15 C23 1.549(4) . ?
C15 C16 1.561(3) . ?
C16 C17 1.475(4) . ?
C17 C22 1.391(3) . ?
C17 C18 1.402(4) . ?
C18 C19 1.380(4) . ?
C19 C20 1.400(4) . ?
C20 C21 1.399(4) . ?
C21 C22 1.398(4) . ?
C22 C23 1.507(4) . ?
C25 C28 1.508(16) . ?
C25 C27 1.520(18) . ?
C25 C26 1.530(6) . ?
C25' C28' 1.511(18) . ?
C25' C27' 1.52(2) . ?
C25' C26' 1.532(7) . ?

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
C7 O1 C10 106.4(2) . . ?
C24 O3 C25 122.4(7) . . ?
C24 O3 C25' 119.2(9) . . ?
C6 C1 C2 119.0(2) . . ?
C6 C1 C7 120.2(2) . . ?
C2 C1 C7 120.8(3) . . ?
C3 C2 C1 119.8(3) . . ?
C4 C3 C2 120.8(3) . . ?
C3 C4 C5 119.5(3) . . ?
C6 C5 C4 120.3(3) . . ?
C5 C6 C1 120.5(2) . . ?
C8 C7 O1 109.8(2) . . ?
C8 C7 C1 133.6(3) . . ?
O1 C7 C1 116.5(2) . . ?
C7 C8 C9 107.1(2) . . ?
C10 C9 C8 106.0(2) . . ?
C10 C9 C14 120.8(2) . . ?
C8 C9 C14 133.2(2) . . ?
C9 C10 O1 110.6(2) . . ?
C9 C10 C11 129.8(2) . . ?
O1 C10 C11 119.6(2) . . ?
C10 C11 C12 107.2(2) . . ?
C13 C12 C11 111.5(2) . . ?
C12 C13 C14 111.7(2) . . ?
C9 C14 C13 108.0(2) . . ?
C9 C14 C15 112.94(19) . . ?
C13 C14 C15 112.1(2) . . ?
C24 C15 C23 114.8(2) . . ?
C24 C15 C14 110.5(2) . . ?
C23 C15 C14 113.9(2) . . ?
C24 C15 C16 105.4(2) . . ?
C23 C15 C16 104.3(2) . . ?
C14 C15 C16 107.06(18) . . ?
O2 C16 C17 127.7(2) . . ?
O2 C16 C15 124.4(3) . . ?
C17 C16 C15 107.9(2) . . ?
C22 C17 C18 122.4(3) . . ?
C22 C17 C16 109.8(2) . . ?
C18 C17 C16 127.8(2) . . ?
C19 C18 C17 117.0(3) . . ?
C18 C19 C20 122.1(3) . . ?
C18 C19 Br1 119.5(2) . . ?
C20 C19 Br1 118.4(2) . . ?
C21 C20 C19 120.0(3) . . ?
C22 C21 C20 118.8(3) . . ?
C17 C22 C21 119.7(2) . . ?
C17 C22 C23 112.0(2) . . ?
C21 C22 C23 128.3(2) . . ?
C22 C23 C15 105.59(19) . . ?
O4 C24 O3 125.3(3) . . ?
O4 C24 C15 124.6(3) . . ?
O3 C24 C15 110.1(2) . . ?
O3 C25 C28 103.9(9) . . ?
O3 C25 C27 109.2(10) . . ?
C28 C25 C27 110.3(5) . . ?
O3 C25 C26 107.4(7) . . ?
C28 C25 C26 111.4(10) . . ?
C27 C25 C26 114.1(10) . . ?
O3 C25' C28' 108.5(13) . . ?
O3 C25' C27' 102.4(12) . . ?
C28' C25' C27' 109.1(7) . . ?
O3 C25' C26' 111.9(11) . . ?
C28' C25' C26' 112.0(14) . . ?
C27' C25' C26' 112.6(13) . . ?

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
C6 C1 C2 C3 1.0(5) . . . . ?
C7 C1 C2 C3 179.1(3) . . . . ?
C1 C2 C3 C4 -0.4(5) . . . . ?
C2 C3 C4 C5 -0.2(5) . . . . ?
C3 C4 C5 C6 0.2(5) . . . . ?
C4 C5 C6 C1 0.4(5) . . . . ?
C2 C1 C6 C5 -1.0(5) . . . . ?
C7 C1 C6 C5 -179.1(3) . . . . ?
C10 O1 C7 C8 0.5(3) . . . . ?
C10 O1 C7 C1 -177.2(3) . . . . ?
C6 C1 C7 C8 -1.9(5) . . . . ?
C2 C1 C7 C8 -180.0(3) . . . . ?
C6 C1 C7 O1 175.0(3) . . . . ?
C2 C1 C7 O1 -3.0(4) . . . . ?
O1 C7 C8 C9 -0.5(3) . . . . ?
C1 C7 C8 C9 176.6(3) . . . . ?
C7 C8 C9 C10 0.4(3) . . . . ?
C7 C8 C9 C14 -178.6(3) . . . . ?
C8 C9 C10 O1 0.0(3) . . . . ?
C14 C9 C10 O1 179.0(2) . . . . ?
C8 C9 C10 C11 179.9(3) . . . . ?
C14 C9 C10 C11 -1.0(5) . . . . ?
C7 O1 C10 C9 -0.3(3) . . . . ?
C7 O1 C10 C11 179.8(3) . . . . ?
C9 C10 C11 C12 11.7(4) . . . . ?
O1 C10 C11 C12 -168.3(3) . . . . ?
C10 C11 C12 C13 -41.9(3) . . . . ?
C11 C12 C13 C14 65.8(3) . . . . ?
C10 C9 C14 C13 20.1(4) . . . . ?
C8 C9 C14 C13 -161.1(3) . . . . ?
C10 C9 C14 C15 144.7(3) . . . . ?
C8 C9 C14 C15 -36.5(4) . . . . ?
C12 C13 C14 C9 -51.1(3) . . . . ?
C12 C13 C14 C15 -176.1(2) . . . . ?
C9 C14 C15 C24 72.6(3) . . . . ?
C13 C14 C15 C24 -165.1(2) . . . . ?
C9 C14 C15 C23 -58.4(3) . . . . ?
C13 C14 C15 C23 63.9(3) . . . . ?
C9 C14 C15 C16 -173.1(2) . . . . ?
C13 C14 C15 C16 -50.8(3) . . . . ?
C24 C15 C16 O2 53.1(3) . . . . ?
C23 C15 C16 O2 174.4(2) . . . . ?
C14 C15 C16 O2 -64.6(3) . . . . ?
C24 C15 C16 C17 -127.9(2) . . . . ?
C23 C15 C16 C17 -6.6(3) . . . . ?
C14 C15 C16 C17 114.4(2) . . . . ?
O2 C16 C17 C22 -176.2(3) . . . . ?
C15 C16 C17 C22 4.8(3) . . . . ?
O2 C16 C17 C18 6.3(4) . . . . ?
C15 C16 C17 C18 -172.7(2) . . . . ?
C22 C17 C18 C19 -0.1(4) . . . . ?
C16 C17 C18 C19 177.1(2) . . . . ?
C17 C18 C19 C20 2.0(4) . . . . ?
C17 C18 C19 Br1 -176.58(18) . . . . ?
C18 C19 C20 C21 -1.8(4) . . . . ?
Br1 C19 C20 C21 176.80(19) . . . . ?
C19 C20 C21 C22 -0.4(4) . . . . ?
C18 C17 C22 C21 -2.1(4) . . . . ?
C16 C17 C22 C21 -179.7(2) . . . . ?
C18 C17 C22 C23 176.8(2) . . . . ?
C16 C17 C22 C23 -0.9(3) . . . . ?
C20 C21 C22 C17 2.3(4) . . . . ?
C20 C21 C22 C23 -176.4(2) . . . . ?
C17 C22 C23 C15 -3.4(3) . . . . ?
C21 C22 C23 C15 175.3(3) . . . . ?
C24 C15 C23 C22 120.8(2) . . . . ?
C14 C15 C23 C22 -110.4(2) . . . . ?
C16 C15 C23 C22 5.9(3) . . . . ?
C25 O3 C24 O4 5.7(7) . . . . ?
C25' O3 C24 O4 -2.8(9) . . . . ?
C25 O3 C24 C15 -171.4(6) . . . . ?
C25' O3 C24 C15 -179.9(9) . . . . ?
C23 C15 C24 O4 141.8(3) . . . . ?
C14 C15 C24 O4 11.3(3) . . . . ?
C16 C15 C24 O4 -104.0(3) . . . . ?
C23 C15 C24 O3 -41.0(3) . . . . ?
C14 C15 C24 O3 -171.5(2) . . . . ?
C16 C15 C24 O3 73.1(3) . . . . ?
C24 O3 C25 C28 171.7(5) . . . . ?
C25' O3 C25 C28 -120(13) . . . . ?
C24 O3 C25 C27 54.0(6) . . . . ?
C25' O3 C25 C27 123(13) . . . . ?
C24 O3 C25 C26 -70.2(13) . . . . ?
C25' O3 C25 C26 -2(12) . . . . ?
C24 O3 C25' C28' 72.7(9) . . . . ?
C25 O3 C25' C28' -43(12) . . . . ?
C24 O3 C25' C27' -172.0(5) . . . . ?
C25 O3 C25' C27' 72(12) . . . . ?
C24 O3 C25' C26' -51.3(18) . . . . ?
C25 O3 C25' C26' -167(14) . . . . ?

_refine_diff_density_max         0.480
_refine_diff_density_min         -0.321
_refine_diff_density_rms         0.068
_shelxl_version_number           2014-3
_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: hexane'
####################################################################### 
# 
# 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_CV469-1
_database_code_depnum_ccdc_archive 'CCDC 1046069'
_audit_update_record             
;
2015-01-28 deposited with the CCDC.
2015-04-27 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C14 H14 O2'
_chemical_formula_weight         214.25
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'

_symmetry_cell_setting           Monoclinic
_space_group_IT_number           5
_symmetry_space_group_name_H-M   C2
_space_group_name_Hall           'C 2y'

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

_cell_length_a                   22.183(11)
_cell_length_b                   7.950(3)
_cell_length_c                   15.744(8)
_cell_angle_alpha                90
_cell_angle_beta                 122.929(5)
_cell_angle_gamma                90
_cell_volume                     2330.6(19)
_cell_formula_units_Z            8
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    ?
_cell_measurement_theta_min      ?
_cell_measurement_theta_max      ?

_exptl_crystal_description       Prism
_exptl_crystal_colour            Colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.221
_exptl_crystal_F_000             912
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.20
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.20
_exptl_absorpt_coefficient_mu    0.081
_shelx_estimated_absorpt_T_min   0.984
_shelx_estimated_absorpt_T_max   0.984
_exptl_absorpt_correction_type   empirical
_exptl_absorpt_correction_T_min  0.757
_exptl_absorpt_correction_T_max  0.984
_exptl_absorpt_process_details   
; 
 SADABS Version 2008/1 Bruker-Nonius
 Blessing, Acta Cryst. (1995) A51 33-38
;
_exptl_special_details           
; 
 It should be noted that the esd's of the cell dimensions are probably too low;
 they should be multiplied by a factor of 2 to 10
;
_diffrn_ambient_temperature      100(2)
_diffrn_measurement_specimen_support 'magnetic support with MicroMount'
_diffrn_radiation_wavelength     0.7107
_diffrn_radiation_type           MoK\a
_diffrn_source                   'Microfocus rotating anode X-ray tube'
_diffrn_source_type              'Rigaku MicroMax-007HF'
_diffrn_source_power             50
_diffrn_source_current           24
_diffrn_source_size              '0.2 mm x 0.2 mm fine focus'
_diffrn_radiation_monochromator  'Confocal Max Flux optic'
_diffrn_detector_type            'PILATUS 200K'
_diffrn_measurement_device_type  '1/4chi goniometer'
_diffrn_measurement_method       
;
 Fullsphere data collection, phi and omega scans
;
_diffrn_detector_area_resol_mean 512
_diffrn_reflns_number            70335
_diffrn_reflns_av_unetI/netI     0.0254
_diffrn_reflns_av_R_equivalents  0.0226
_diffrn_reflns_limit_h_min       -48
_diffrn_reflns_limit_h_max       48
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_l_min       -34
_diffrn_reflns_limit_l_max       34
_diffrn_reflns_theta_min         3.291
_diffrn_reflns_theta_max         52.126
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.981
_diffrn_measured_fraction_theta_full 0.993
_diffrn_reflns_Laue_measured_fraction_max 0.981
_diffrn_reflns_Laue_measured_fraction_full 0.993
_diffrn_reflns_point_group_measured_fraction_max 0.943
_diffrn_reflns_point_group_measured_fraction_full 0.992
_reflns_number_total             25244
_reflns_number_gt                21456
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.844
_reflns_Friedel_fraction_max     0.901
_reflns_Friedel_fraction_full    0.991

_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 APEX2 v2011.4-0'
_computing_cell_refinement       'Bruker APEX2 v2011.4-0'
_computing_data_reduction        'Bruker SAINT V7.60A'
_computing_structure_solution    Sir2011
_computing_structure_refinement  'SHELXL-2014 (Sheldrick, 2014)'
_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)+(0.0631P)²+0.0391P] 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_abs_structure_details 
;
 Flack x determined using 8723 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_chemical_absolute_configuration ad
_refine_ls_abs_structure_Flack   0.09(10)
_refine_ls_number_reflns         25244
_refine_ls_number_parameters     292
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0497
_refine_ls_R_factor_gt           0.0373
_refine_ls_wR_factor_ref         0.1022
_refine_ls_wR_factor_gt          0.0947
_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_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 0.24547(3) 0.20804(6) 0.74456(3) 0.01193(6) Uani 1 1 d . . . . .
C2 C 0.32484(3) 0.16753(6) 0.78117(4) 0.01313(6) Uani 1 1 d . . . . .
C3 C 0.36480(3) 0.32741(7) 0.81025(4) 0.01385(7) Uani 1 1 d . . . . .
C4 C 0.43671(3) 0.35461(9) 0.84382(5) 0.01969(9) Uani 1 1 d . . . . .
H4 H 0.4670 0.2639 0.8508 0.024 Uiso 1 1 calc R U . . .
C5 C 0.46250(4) 0.51869(11) 0.86664(7) 0.02496(12) Uani 1 1 d . . . . .
H5 H 0.5113 0.5409 0.8905 0.030 Uiso 1 1 calc R U . . .
C6 C 0.41694(4) 0.65150(9) 0.85459(7) 0.02492(12) Uani 1 1 d . . . . .
H6 H 0.4352 0.7631 0.8693 0.030 Uiso 1 1 calc R U . . .
C7 C 0.34553(4) 0.62341(8) 0.82157(5) 0.01984(9) Uani 1 1 d . . . . .
H7 H 0.3150 0.7142 0.8137 0.024 Uiso 1 1 calc R U . . .
C8 C 0.31973(3) 0.45868(6) 0.80028(4) 0.01371(6) Uani 1 1 d . . . . .
C9 C 0.24600(3) 0.39679(6) 0.76748(4) 0.01375(7) Uani 1 1 d . . . . .
H9A H 0.2087 0.4577 0.7064 0.016 Uiso 1 1 calc R U . . .
H9B H 0.2370 0.4133 0.8220 0.016 Uiso 1 1 calc R U . . .
C10 C 0.21917(3) 0.09255(6) 0.79781(3) 0.01249(6) Uani 1 1 d . . . . .
H10 H 0.2223 -0.0266 0.7802 0.015 Uiso 1 1 calc R U . . .
C11 C 0.26353(3) 0.10796(6) 0.91155(3) 0.01263(6) Uani 1 1 d . . . . .
C12 C 0.33950(3) 0.09062(7) 0.98502(4) 0.01471(7) Uani 1 1 d . . . . .
H12 H 0.3759 0.0768 0.9712 0.018 Uiso 1 1 calc R U . . .
C13 C 0.34909(3) 0.09785(7) 1.07836(4) 0.01377(6) Uani 1 1 d . . . . .
C14 C 0.15545(3) 0.12602(9) 0.92931(4) 0.01723(8) Uani 1 1 d . . . . .
H14A H 0.1395 0.2424 0.9291 0.021 Uiso 1 1 calc R U . . .
H14B H 0.1469 0.0564 0.9739 0.021 Uiso 1 1 calc R U . . .
C15 C 0.11388(3) 0.05412(8) 0.82120(4) 0.01674(8) Uani 1 1 d . . . . .
H15A H 0.1204 -0.0694 0.8243 0.020 Uiso 1 1 calc R U . . .
H15B H 0.0620 0.0774 0.7888 0.020 Uiso 1 1 calc R U . . .
C16 C 0.13955(3) 0.13076(8) 0.75690(4) 0.01513(7) Uani 1 1 d . . . . .
H16A H 0.1328 0.2542 0.7540 0.018 Uiso 1 1 calc R U . . .
H16B H 0.1093 0.0868 0.6870 0.018 Uiso 1 1 calc R U . . .
C17 C 0.41024(3) 0.06762(7) 1.18119(4) 0.01437(7) Uani 1 1 d . . . . .
C18 C 0.47222(3) -0.01171(9) 1.19804(5) 0.01935(9) Uani 1 1 d . . . . .
H18 H 0.4764 -0.0359 1.1424 0.023 Uiso 1 1 calc R U . . .
C19 C 0.52778(4) -0.05544(10) 1.29567(5) 0.02367(11) Uani 1 1 d . . . . .
H19 H 0.5698 -0.1080 1.3062 0.028 Uiso 1 1 calc R U . . .
C20 C 0.52194(4) -0.02228(10) 1.37797(5) 0.02359(11) Uani 1 1 d . . . . .
H20 H 0.5590 -0.0557 1.4442 0.028 Uiso 1 1 calc R U . . .
C21 C 0.46115(4) 0.06044(10) 1.36191(4) 0.02142(10) Uani 1 1 d . . . . .
H21 H 0.4574 0.0857 1.4178 0.026 Uiso 1 1 calc R U . . .
C22 C 0.40586(3) 0.10634(8) 1.26460(4) 0.01662(8) Uani 1 1 d . . . . .
H22 H 0.3650 0.1641 1.2547 0.020 Uiso 1 1 calc R U . . .
C23 C 0.19936(3) 0.17568(7) 0.62945(4) 0.01444(7) Uani 1 1 d . . . . .
C24 C 0.15368(4) -0.05979(10) 0.50803(5) 0.02061(10) Uani 1 1 d . . . . .
C25 C 0.07432(4) -0.01844(14) 0.45597(7) 0.03183(16) Uani 1 1 d . . . . .
H25A H 0.0575 -0.0525 0.4995 0.048 Uiso 1 1 calc R U . . .
H25B H 0.0471 -0.0790 0.3915 0.048 Uiso 1 1 calc R U . . .
H25C H 0.0672 0.1029 0.4434 0.048 Uiso 1 1 calc R U . . .
C26 C 0.18532(7) 0.00203(18) 0.44910(8) 0.0403(3) Uani 1 1 d . . . . .
H26A H 0.1781 0.1238 0.4388 0.060 Uiso 1 1 calc R U . . .
H26B H 0.1614 -0.0547 0.3833 0.060 Uiso 1 1 calc R U . . .
H26C H 0.2368 -0.0231 0.4872 0.060 Uiso 1 1 calc R U . . .
C27 C 0.16693(5) -0.24750(12) 0.53017(8) 0.03191(16) Uani 1 1 d . . . . .
H27A H 0.2187 -0.2688 0.5723 0.048 Uiso 1 1 calc R U . . .
H27B H 0.1461 -0.3095 0.4664 0.048 Uiso 1 1 calc R U . . .
H27C H 0.1445 -0.2849 0.5660 0.048 Uiso 1 1 calc R U . . .
C28 C 0.23284(3) 0.12433(7) 0.96610(4) 0.01361(6) Uani 1 1 d . . . . .
O2 O 0.34856(3) 0.02758(6) 0.78598(4) 0.01972(7) Uani 1 1 d . . . . .
O1 O 0.28379(2) 0.12063(6) 1.06785(3) 0.01461(6) Uani 1 1 d . . . . .
O3 O 0.19401(3) 0.01112(6) 0.61146(3) 0.01745(7) Uani 1 1 d . . . . .
O4 O 0.17299(3) 0.28551(7) 0.56622(4) 0.02388(9) 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 C9 1.5420(9) . ?
C1 C23 1.5432(10) . ?
C1 C10 1.5552(8) . ?
C1 C2 1.5596(11) . ?
C2 O2 1.2155(8) . ?
C2 C3 1.4730(9) . ?
C3 C8 1.3939(9) . ?
C3 C4 1.3979(11) . ?
C4 C5 1.3909(12) . ?
C5 C6 1.4014(13) . ?
C6 C7 1.3908(12) . ?
C7 C8 1.3952(9) . ?
C8 C9 1.5050(11) . ?
C10 C11 1.5080(10) . ?
C10 C16 1.5457(11) . ?
C11 C28 1.3616(8) . ?
C11 C12 1.4414(10) . ?
C12 C13 1.3669(10) . ?
C13 O1 1.3775(10) . ?
C13 C17 1.4599(9) . ?
C14 C28 1.4837(11) . ?
C14 C15 1.5388(11) . ?
C15 C16 1.5322(9) . ?
C17 C18 1.4009(10) . ?
C17 C22 1.4025(10) . ?
C18 C19 1.3939(10) . ?
C19 C20 1.3956(13) . ?
C20 C21 1.3944(13) . ?
C21 C22 1.3935(9) . ?
C23 O4 1.2094(8) . ?
C23 O3 1.3302(9) . ?
C24 O3 1.4786(10) . ?
C24 C26 1.5176(12) . ?
C24 C25 1.5200(14) . ?
C24 C27 1.5243(14) . ?
C28 O1 1.3697(9) . ?

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 C1 C23 110.67(4) . . ?
C9 C1 C10 113.94(4) . . ?
C23 C1 C10 109.35(5) . . ?
C9 C1 C2 104.53(4) . . ?
C23 C1 C2 107.10(4) . . ?
C10 C1 C2 110.97(4) . . ?
O2 C2 C3 127.13(6) . . ?
O2 C2 C1 125.14(5) . . ?
C3 C2 C1 107.72(5) . . ?
C8 C3 C4 121.88(6) . . ?
C8 C3 C2 109.72(6) . . ?
C4 C3 C2 128.41(5) . . ?
C5 C4 C3 117.86(6) . . ?
C4 C5 C6 120.44(7) . . ?
C7 C6 C5 121.38(7) . . ?
C6 C7 C8 118.40(6) . . ?
C3 C8 C7 120.02(6) . . ?
C3 C8 C9 111.90(5) . . ?
C7 C8 C9 128.07(5) . . ?
C8 C9 C1 105.49(4) . . ?
C11 C10 C16 109.82(4) . . ?
C11 C10 C1 113.47(5) . . ?
C16 C10 C1 109.74(5) . . ?
C28 C11 C12 105.68(6) . . ?
C28 C11 C10 121.97(6) . . ?
C12 C11 C10 131.97(4) . . ?
C13 C12 C11 106.83(5) . . ?
C12 C13 O1 109.72(4) . . ?
C12 C13 C17 133.88(6) . . ?
O1 C13 C17 115.93(5) . . ?
C28 C14 C15 107.40(4) . . ?
C16 C15 C14 111.63(6) . . ?
C15 C16 C10 113.41(5) . . ?
C18 C17 C22 118.81(5) . . ?
C18 C17 C13 120.58(6) . . ?
C22 C17 C13 120.45(6) . . ?
C19 C18 C17 120.63(6) . . ?
C18 C19 C20 120.28(8) . . ?
C21 C20 C19 119.30(6) . . ?
C22 C21 C20 120.62(7) . . ?
C21 C22 C17 120.30(7) . . ?
O4 C23 O3 125.99(6) . . ?
O4 C23 C1 124.16(6) . . ?
O3 C23 C1 109.85(4) . . ?
O3 C24 C26 110.23(7) . . ?
O3 C24 C25 109.97(6) . . ?
C26 C24 C25 112.66(9) . . ?
O3 C24 C27 101.27(6) . . ?
C26 C24 C27 111.17(8) . . ?
C25 C24 C27 110.97(7) . . ?
C11 C28 O1 110.98(6) . . ?
C11 C28 C14 128.58(5) . . ?
O1 C28 C14 120.06(4) . . ?
C28 O1 C13 106.78(5) . . ?
C23 O3 C24 122.69(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 O2 172.00(5) . . . . ?
C23 C1 C2 O2 -70.53(6) . . . . ?
C10 C1 C2 O2 48.75(7) . . . . ?
C9 C1 C2 C3 -6.75(5) . . . . ?
C23 C1 C2 C3 110.72(4) . . . . ?
C10 C1 C2 C3 -130.00(5) . . . . ?
O2 C2 C3 C8 -175.77(5) . . . . ?
C1 C2 C3 C8 2.95(5) . . . . ?
O2 C2 C3 C4 3.96(9) . . . . ?
C1 C2 C3 C4 -177.31(5) . . . . ?
C8 C3 C4 C5 -0.52(9) . . . . ?
C2 C3 C4 C5 179.77(6) . . . . ?
C3 C4 C5 C6 -0.89(11) . . . . ?
C4 C5 C6 C7 1.21(13) . . . . ?
C5 C6 C7 C8 -0.07(11) . . . . ?
C4 C3 C8 C7 1.67(8) . . . . ?
C2 C3 C8 C7 -178.58(5) . . . . ?
C4 C3 C8 C9 -177.44(5) . . . . ?
C2 C3 C8 C9 2.32(6) . . . . ?
C6 C7 C8 C3 -1.34(9) . . . . ?
C6 C7 C8 C9 177.61(6) . . . . ?
C3 C8 C9 C1 -6.60(6) . . . . ?
C7 C8 C9 C1 174.38(5) . . . . ?
C23 C1 C9 C8 -107.17(5) . . . . ?
C10 C1 C9 C8 129.13(5) . . . . ?
C2 C1 C9 C8 7.82(5) . . . . ?
C9 C1 C10 C11 -58.69(6) . . . . ?
C23 C1 C10 C11 176.90(4) . . . . ?
C2 C1 C10 C11 58.97(6) . . . . ?
C9 C1 C10 C16 64.59(6) . . . . ?
C23 C1 C10 C16 -59.83(5) . . . . ?
C2 C1 C10 C16 -177.75(4) . . . . ?
C16 C10 C11 C28 10.27(7) . . . . ?
C1 C10 C11 C28 133.50(5) . . . . ?
C16 C10 C11 C12 -177.85(6) . . . . ?
C1 C10 C11 C12 -54.62(8) . . . . ?
C28 C11 C12 C13 -0.03(6) . . . . ?
C10 C11 C12 C13 -172.88(5) . . . . ?
C11 C12 C13 O1 -0.69(6) . . . . ?
C11 C12 C13 C17 170.86(6) . . . . ?
C28 C14 C15 C16 -46.07(7) . . . . ?
C14 C15 C16 C10 62.31(7) . . . . ?
C11 C10 C16 C15 -41.16(7) . . . . ?
C1 C10 C16 C15 -166.55(4) . . . . ?
C12 C13 C17 C18 -12.87(10) . . . . ?
O1 C13 C17 C18 158.28(6) . . . . ?
C12 C13 C17 C22 171.82(6) . . . . ?
O1 C13 C17 C22 -17.03(8) . . . . ?
C22 C17 C18 C19 1.68(10) . . . . ?
C13 C17 C18 C19 -173.70(6) . . . . ?
C17 C18 C19 C20 0.72(11) . . . . ?
C18 C19 C20 C21 -2.31(12) . . . . ?
C19 C20 C21 C22 1.49(11) . . . . ?
C20 C21 C22 C17 0.92(10) . . . . ?
C18 C17 C22 C21 -2.49(9) . . . . ?
C13 C17 C22 C21 172.90(6) . . . . ?
C9 C1 C23 O4 6.33(8) . . . . ?
C10 C1 C23 O4 132.63(7) . . . . ?
C2 C1 C23 O4 -107.04(7) . . . . ?
C9 C1 C23 O3 -174.25(5) . . . . ?
C10 C1 C23 O3 -47.94(6) . . . . ?
C2 C1 C23 O3 72.38(5) . . . . ?
C12 C11 C28 O1 0.75(6) . . . . ?
C10 C11 C28 O1 174.48(5) . . . . ?
C12 C11 C28 C14 -172.10(6) . . . . ?
C10 C11 C28 C14 1.64(9) . . . . ?
C15 C14 C28 C11 16.49(9) . . . . ?
C15 C14 C28 O1 -155.79(5) . . . . ?
C11 C28 O1 C13 -1.17(6) . . . . ?
C14 C28 O1 C13 172.37(5) . . . . ?
C12 C13 O1 C28 1.13(6) . . . . ?
C17 C13 O1 C28 -172.10(5) . . . . ?
O4 C23 O3 C24 0.04(10) . . . . ?
C1 C23 O3 C24 -179.37(5) . . . . ?
C26 C24 O3 C23 60.20(10) . . . . ?
C25 C24 O3 C23 -64.60(8) . . . . ?
C27 C24 O3 C23 177.96(6) . . . . ?

_refine_diff_density_max         0.486
_refine_diff_density_min         -0.247
_refine_diff_density_rms         0.055
_shelxl_version_number           2014-3
_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: hexane'
