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

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

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C27 H29 Cl O3'
_chemical_formula_weight         436.95

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'
Cl Cl 0.1484 0.1585 '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           Orthorhombic
_symmetry_space_group_name_H-M   Pbca

loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'x+1/2, -y+1/2, -z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, y, -z-1/2'
'-x-1/2, y-1/2, z'
'x, -y-1/2, z-1/2'

_cell_length_a                   8.310(6)
_cell_length_b                   8.664(6)
_cell_length_c                   65.12(4)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_volume                     4688(6)
_cell_formula_units_Z            8
_cell_measurement_temperature    283(2)
_cell_measurement_reflns_used    ?
_cell_measurement_theta_min      ?
_cell_measurement_theta_max      ?

_exptl_crystal_description       needle
_exptl_crystal_colour            yellow
_exptl_crystal_size_max          0.16
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.14
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.238
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1856
_exptl_absorpt_coefficient_mu    0.188
_exptl_absorpt_correction_type   ?
_exptl_absorpt_correction_T_min  0.9705
_exptl_absorpt_correction_T_max  0.9741
_exptl_absorpt_process_details   ?

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      283(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  ?
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            19076
_diffrn_reflns_av_R_equivalents  0.0681
_diffrn_reflns_av_sigmaI/netI    0.0659
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_l_min       -86
_diffrn_reflns_limit_l_max       70
_diffrn_reflns_theta_min         0.63
_diffrn_reflns_theta_max         28.16
_reflns_number_total             5205
_reflns_number_gt                2137
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    ?
_computing_publication_material  ?

_refine_special_details          
; 
 Refinement of F² against ALL reflections.  The weighted R-factor wR and 
 goodness of fit S are based on F², conventional R-factors R are based 
 on F, with F set to zero for negative F². The threshold expression of 
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is 
 not relevant to the choice of reflections for refinement.  R-factors based 
 on F² are statistically about twice as large as those based on F, and R- 
 factors based on ALL data will be even larger. 
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.1000P)²+0.0000P] 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       0.0036(8)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         5205
_refine_ls_number_parameters     282
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1715
_refine_ls_R_factor_gt           0.0776
_refine_ls_wR_factor_ref         0.2468
_refine_ls_wR_factor_gt          0.1805
_refine_ls_goodness_of_fit_ref   1.073
_refine_ls_restrained_S_all      1.073
_refine_ls_shift/su_max          0.029
_refine_ls_shift/su_mean         0.001

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
Cl1 Cl 0.39011(13) -0.47878(12) -0.411312(18) 0.1000(5) Uani 1 1 d . . .
O1 O 0.6037(3) -0.9578(3) -0.40798(4) 0.0688(7) Uani 1 1 d . . .
O3 O 0.5040(4) -1.5205(4) -0.30853(6) 0.1229(11) Uani 1 1 d . . .
O5 O 0.4933(3) -1.3030(3) -0.49122(4) 0.0772(7) Uani 1 1 d . . .
C1 C 0.6219(4) -0.8795(4) -0.42724(5) 0.0673(9) Uani 1 1 d . . .
H1 H 0.7326 -0.8412 -0.4283 0.081 Uiso 1 1 calc R . .
C2 C 0.5066(4) -0.7426(4) -0.42857(6) 0.0689(9) Uani 1 1 d . . .
H2A H 0.5263 -0.6858 -0.4412 0.083 Uiso 1 1 calc R . .
H2B H 0.3965 -0.7796 -0.4288 0.083 Uiso 1 1 calc R . .
C3 C 0.5298(4) -0.6377(4) -0.41043(5) 0.0692(10) Uani 1 1 d . . .
H3 H 0.6391 -0.5955 -0.4111 0.083 Uiso 1 1 calc R . .
C4 C 0.5133(4) -0.7261(4) -0.39074(6) 0.0734(10) Uani 1 1 d . . .
H4A H 0.4048 -0.7662 -0.3895 0.088 Uiso 1 1 calc R . .
H4B H 0.5340 -0.6586 -0.3792 0.088 Uiso 1 1 calc R . .
C5 C 0.6334(4) -0.8583(4) -0.39080(6) 0.0736(10) Uani 1 1 d . . .
H5 H 0.7414 -0.8145 -0.3924 0.088 Uiso 1 1 calc R . .
C6 C 0.5931(4) -0.9953(3) -0.44412(5) 0.0610(9) Uani 1 1 d . . .
C7 C 0.4731(4) -1.1060(4) -0.44259(6) 0.0775(11) Uani 1 1 d . . .
H7 H 0.4120 -1.1126 -0.4307 0.093 Uiso 1 1 calc R . .
C8 C 0.4440(4) -1.2055(4) -0.45849(6) 0.0748(10) Uani 1 1 d . . .
H8 H 0.3639 -1.2798 -0.4572 0.090 Uiso 1 1 calc R . .
C9 C 0.5319(4) -1.1969(4) -0.47649(5) 0.0624(9) Uani 1 1 d . . .
C10 C 0.6513(4) -1.0894(4) -0.47805(5) 0.0691(9) Uani 1 1 d . . .
H10 H 0.7119 -1.0826 -0.4900 0.083 Uiso 1 1 calc R . .
C11 C 0.6820(4) -0.9908(4) -0.46187(6) 0.0691(9) Uani 1 1 d . . .
H11 H 0.7651 -0.9194 -0.4630 0.083 Uiso 1 1 calc R . .
C12 C 0.5847(5) -1.3008(4) -0.50962(6) 0.0830(11) Uani 1 1 d . . .
H12A H 0.5461 -1.3795 -0.5187 0.125 Uiso 1 1 calc R . .
H12B H 0.6959 -1.3195 -0.5065 0.125 Uiso 1 1 calc R . .
H12C H 0.5741 -1.2017 -0.5161 0.125 Uiso 1 1 calc R . .
C13 C 0.6334(4) -0.9609(5) -0.37169(6) 0.0833(11) Uani 1 1 d . . .
H13A H 0.7127 -1.0419 -0.3735 0.100 Uiso 1 1 calc R . .
H13B H 0.6657 -0.8995 -0.3599 0.100 Uiso 1 1 calc R . .
C14 C 0.4757(5) -1.0324(6) -0.36731(7) 0.1053(14) Uani 1 1 d . . .
H14A H 0.4299 -1.0701 -0.3801 0.126 Uiso 1 1 calc R . .
H14B H 0.4038 -0.9542 -0.3619 0.126 Uiso 1 1 calc R . .
C15 C 0.4856(5) -1.1680(5) -0.35176(7) 0.0905(12) Uani 1 1 d . . .
C16 C 0.5495(7) -1.1493(6) -0.33243(7) 0.1276(18) Uani 1 1 d . . .
H16 H 0.5900 -1.0533 -0.3287 0.153 Uiso 1 1 calc R . .
C17 C 0.5552(7) -1.2682(6) -0.31855(8) 0.1290(18) Uani 1 1 d . . .
H17 H 0.5980 -1.2521 -0.3055 0.155 Uiso 1 1 calc R . .
C18 C 0.4979(5) -1.4107(5) -0.32391(7) 0.0907(12) Uani 1 1 d . . .
C19 C 0.4340(5) -1.4325(5) -0.34297(7) 0.0927(12) Uani 1 1 d . . .
H19 H 0.3932 -1.5284 -0.3467 0.111 Uiso 1 1 calc R . .
C20 C 0.4307(5) -1.3108(6) -0.35664(7) 0.0947(12) Uani 1 1 d . . .
H20 H 0.3891 -1.3273 -0.3697 0.114 Uiso 1 1 calc R . .
C21 C 0.4591(6) -1.6708(6) -0.31272(8) 0.1232(16) Uani 1 1 d . . .
H21A H 0.5228 -1.7109 -0.3240 0.148 Uiso 1 1 calc R . .
H21B H 0.3466 -1.6740 -0.3167 0.148 Uiso 1 1 calc R . .
C22 C 0.4851(7) -1.7677(6) -0.29385(8) 0.1059(14) Uani 1 1 d . . .
C23 C 0.6057(7) -1.7382(6) -0.28017(10) 0.1151(16) Uani 1 1 d . . .
H23 H 0.6690 -1.6505 -0.2818 0.138 Uiso 1 1 calc R . .
C24 C 0.6347(7) -1.8348(9) -0.26422(10) 0.1312(18) Uani 1 1 d . . .
H24 H 0.7159 -1.8121 -0.2549 0.157 Uiso 1 1 calc R . .
C25 C 0.5476(10) -1.9614(8) -0.26198(11) 0.137(2) Uani 1 1 d . . .
H25 H 0.5696 -2.0278 -0.2511 0.165 Uiso 1 1 calc R . .
C26 C 0.4295(10) -1.9957(7) -0.27490(13) 0.147(2) Uani 1 1 d . . .
H26 H 0.3697 -2.0853 -0.2730 0.177 Uiso 1 1 calc R . .
C27 C 0.3952(7) -1.9004(8) -0.29102(10) 0.1351(19) Uani 1 1 d . . .
H27 H 0.3121 -1.9245 -0.3000 0.162 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
Cl1 C3 1.802(4) . ?
O1 C5 1.434(4) . ?
O1 C1 1.434(4) . ?
O3 C21 1.382(5) . ?
O3 C18 1.382(5) . ?
O5 C9 1.367(4) . ?
O5 C12 1.419(4) . ?
C1 C6 1.507(4) . ?
C1 C2 1.527(4) . ?
C1 H1 0.9800 . ?
C2 C3 1.503(4) . ?
C2 H2A 0.9700 . ?
C2 H2B 0.9700 . ?
C3 C4 1.500(5) . ?
C3 H3 0.9800 . ?
C4 C5 1.519(5) . ?
C4 H4A 0.9700 . ?
C4 H4B 0.9700 . ?
C5 C13 1.529(5) . ?
C5 H5 0.9800 . ?
C6 C11 1.372(5) . ?
C6 C7 1.387(4) . ?
C7 C8 1.369(5) . ?
C7 H7 0.9300 . ?
C8 C9 1.383(5) . ?
C8 H8 0.9300 . ?
C9 C10 1.364(4) . ?
C10 C11 1.381(4) . ?
C10 H10 0.9300 . ?
C11 H11 0.9300 . ?
C12 H12A 0.9600 . ?
C12 H12B 0.9600 . ?
C12 H12C 0.9600 . ?
C13 C14 1.477(5) . ?
C13 H13A 0.9700 . ?
C13 H13B 0.9700 . ?
C14 C15 1.553(6) . ?
C14 H14A 0.9700 . ?
C14 H14B 0.9700 . ?
C15 C20 1.356(6) . ?
C15 C16 1.376(6) . ?
C16 C17 1.372(6) . ?
C16 H16 0.9300 . ?
C17 C18 1.369(6) . ?
C17 H17 0.9300 . ?
C18 C19 1.363(5) . ?
C19 C20 1.380(6) . ?
C19 H19 0.9300 . ?
C20 H20 0.9300 . ?
C21 C22 1.504(6) . ?
C21 H21A 0.9700 . ?
C21 H21B 0.9700 . ?
C22 C23 1.365(7) . ?
C22 C27 1.383(7) . ?
C23 C24 1.356(7) . ?
C23 H23 0.9300 . ?
C24 C25 1.322(8) . ?
C24 H24 0.9300 . ?
C25 C26 1.326(8) . ?
C25 H25 0.9300 . ?
C26 C27 1.365(8) . ?
C26 H26 0.9300 . ?
C27 H27 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
C5 O1 C1 112.3(3) . . ?
C21 O3 C18 119.7(4) . . ?
C9 O5 C12 117.2(3) . . ?
O1 C1 C6 107.8(3) . . ?
O1 C1 C2 110.5(3) . . ?
C6 C1 C2 112.1(3) . . ?
O1 C1 H1 108.8 . . ?
C6 C1 H1 108.8 . . ?
C2 C1 H1 108.8 . . ?
C3 C2 C1 110.2(3) . . ?
C3 C2 H2A 109.6 . . ?
C1 C2 H2A 109.6 . . ?
C3 C2 H2B 109.6 . . ?
C1 C2 H2B 109.6 . . ?
H2A C2 H2B 108.1 . . ?
C4 C3 C2 110.6(3) . . ?
C4 C3 Cl1 111.0(2) . . ?
C2 C3 Cl1 110.8(2) . . ?
C4 C3 H3 108.1 . . ?
C2 C3 H3 108.1 . . ?
Cl1 C3 H3 108.1 . . ?
C3 C4 C5 108.9(3) . . ?
C3 C4 H4A 109.9 . . ?
C5 C4 H4A 109.9 . . ?
C3 C4 H4B 109.9 . . ?
C5 C4 H4B 109.9 . . ?
H4A C4 H4B 108.3 . . ?
O1 C5 C4 110.0(3) . . ?
O1 C5 C13 106.6(3) . . ?
C4 C5 C13 115.9(3) . . ?
O1 C5 H5 108.0 . . ?
C4 C5 H5 108.0 . . ?
C13 C5 H5 108.0 . . ?
C11 C6 C7 117.8(3) . . ?
C11 C6 C1 120.6(3) . . ?
C7 C6 C1 121.5(3) . . ?
C8 C7 C6 120.6(3) . . ?
C8 C7 H7 119.7 . . ?
C6 C7 H7 119.7 . . ?
C7 C8 C9 120.9(3) . . ?
C7 C8 H8 119.6 . . ?
C9 C8 H8 119.6 . . ?
C10 C9 O5 125.3(3) . . ?
C10 C9 C8 119.0(3) . . ?
O5 C9 C8 115.7(3) . . ?
C9 C10 C11 120.0(3) . . ?
C9 C10 H10 120.0 . . ?
C11 C10 H10 120.0 . . ?
C6 C11 C10 121.7(3) . . ?
C6 C11 H11 119.1 . . ?
C10 C11 H11 119.1 . . ?
O5 C12 H12A 109.5 . . ?
O5 C12 H12B 109.5 . . ?
H12A C12 H12B 109.5 . . ?
O5 C12 H12C 109.5 . . ?
H12A C12 H12C 109.5 . . ?
H12B C12 H12C 109.5 . . ?
C14 C13 C5 113.6(3) . . ?
C14 C13 H13A 108.8 . . ?
C5 C13 H13A 108.8 . . ?
C14 C13 H13B 108.8 . . ?
C5 C13 H13B 108.8 . . ?
H13A C13 H13B 107.7 . . ?
C13 C14 C15 113.3(3) . . ?
C13 C14 H14A 108.9 . . ?
C15 C14 H14A 108.9 . . ?
C13 C14 H14B 108.9 . . ?
C15 C14 H14B 108.9 . . ?
H14A C14 H14B 107.7 . . ?
C20 C15 C16 116.9(4) . . ?
C20 C15 C14 121.3(4) . . ?
C16 C15 C14 121.9(4) . . ?
C17 C16 C15 121.8(5) . . ?
C17 C16 H16 119.1 . . ?
C15 C16 H16 119.1 . . ?
C18 C17 C16 119.9(4) . . ?
C18 C17 H17 120.1 . . ?
C16 C17 H17 120.1 . . ?
C19 C18 C17 119.5(4) . . ?
C19 C18 O3 125.4(4) . . ?
C17 C18 O3 115.0(4) . . ?
C18 C19 C20 119.3(4) . . ?
C18 C19 H19 120.3 . . ?
C20 C19 H19 120.3 . . ?
C15 C20 C19 122.6(4) . . ?
C15 C20 H20 118.7 . . ?
C19 C20 H20 118.7 . . ?
O3 C21 C22 109.0(4) . . ?
O3 C21 H21A 109.9 . . ?
C22 C21 H21A 109.9 . . ?
O3 C21 H21B 109.9 . . ?
C22 C21 H21B 109.9 . . ?
H21A C21 H21B 108.3 . . ?
C23 C22 C27 117.7(5) . . ?
C23 C22 C21 122.3(6) . . ?
C27 C22 C21 119.7(6) . . ?
C24 C23 C22 121.0(5) . . ?
C24 C23 H23 119.5 . . ?
C22 C23 H23 119.5 . . ?
C25 C24 C23 119.9(6) . . ?
C25 C24 H24 120.0 . . ?
C23 C24 H24 120.0 . . ?
C24 C25 C26 121.4(7) . . ?
C24 C25 H25 119.3 . . ?
C26 C25 H25 119.3 . . ?
C25 C26 C27 120.4(6) . . ?
C25 C26 H26 119.8 . . ?
C27 C26 H26 119.8 . . ?
C26 C27 C22 119.5(6) . . ?
C26 C27 H27 120.3 . . ?
C22 C27 H27 120.3 . . ?

_diffrn_measured_fraction_theta_max 0.908
_diffrn_reflns_theta_full        25.00
_diffrn_measured_fraction_theta_full 0.967
_refine_diff_density_max         0.508
_refine_diff_density_min         -0.314
_refine_diff_density_rms         0.117
_database_code_depnum_ccdc_archive 'CCDC 1027342'
