# Electronic Supplementary Material (ESI) for Organic Chemistry Frontiers.
# This journal is © the Partner Organisations 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_I
_database_code_depnum_ccdc_archive 'CCDC 1404951'
_audit_update_record             
;
2015-06-04 deposited with the CCDC.
2015-12-03 downloaded from the CCDC.
;
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C36 H29 Cl O6'
_chemical_formula_iupac          ?
_chemical_formula_weight         593.04
_chemical_absolute_configuration ad

_chemical_melting_point          ?

_space_group_crystal_system      orthorhombic
_space_group_name_H-M_alt        'P 21 21 21'
_space_group_name_Hall           'P 2ac 2ab'
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                   6.2154(3)
_cell_length_b                   20.2473(13)
_cell_length_c                   22.9882(17)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     2893.0(3)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    1445
_cell_measurement_theta_min      2.8422
_cell_measurement_theta_max      21.7907
_cell_measurement_temperature    103.(2)

_exptl_crystal_description       needle
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.420
_exptl_crystal_size_mid          0.100
_exptl_crystal_size_min          0.080
_exptl_crystal_density_diffrn    1.362
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1240

_exptl_absorpt_coefficient_mu    0.180
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS V2014/4 (Bruker AXS Inc.)'
_exptl_absorpt_correction_T_min  0.82
_exptl_absorpt_correction_T_max  0.99

_exptl_special_details           
;
;

_diffrn_ambient_temperature      103.(2)

_diffrn_source                   'fine-focus sealed tube'
_diffrn_source_type              ?

_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean 8.3333
_diffrn_reflns_number            4464
_diffrn_reflns_av_R_equivalents  0.0782
_diffrn_reflns_av_unetI/netI     0.0750
_diffrn_reflns_theta_min         3.15
_diffrn_reflns_theta_max         29.29
_diffrn_reflns_theta_full        29.29
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measured_fraction_theta_full 0.995
_diffrn_reflns_limit_h_min       -5
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_k_min       -26
_diffrn_reflns_limit_k_max       27
_diffrn_reflns_limit_l_min       -26
_diffrn_reflns_limit_l_max       31

_refine_special_details          
;
;

_reflns_number_total             4464
_reflns_number_gt                3394
_reflns_threshold_expression     'I > 2σ(I)'

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_R_factor_all          0.0801
_refine_ls_R_factor_gt           0.0507
_refine_ls_wR_factor_gt          0.1004
_refine_ls_wR_factor_ref         0.1167
_refine_ls_goodness_of_fit_ref   1.021
_refine_ls_restrained_S_all      1.021
_refine_ls_number_reflns         4464
_refine_ls_number_parameters     388
_refine_ls_number_restraints     0
_refine_ls_number_constraints    ?
_refine_ls_hydrogen_treatment    constr
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0460P)²+1.0074P] where P=(Fo²+2Fc²)/3'

_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?

_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_diff_density_max         0.282
_refine_diff_density_min         -0.298
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_abs_structure_details 
'No quotients, so Flack parameter determined by classical intensity fit'
_refine_ls_abs_structure_Flack   0.44(9)

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'
Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_computing_data_collection       'APEX2 (Bruker AXS Inc., 2014)'
_computing_cell_refinement       'SAINT V8.34A (Bruker AXS Inc., 2013)'
_computing_data_reduction        'SAINT V8.34A (Bruker AXS Inc., 2013)'
_computing_structure_solution    ?
_computing_structure_refinement  'SHELXL-2014/6 (Sheldrick, 2014)'
_computing_molecular_graphics    'XP (Bruker AXS Inc., 2014)'
_computing_publication_material  'APEX2 (Bruker AXS Inc., 2014)'

loop_
_atom_site_type_symbol
_atom_site_label
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_calc_flag
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_refinement_flags_posn
_atom_site_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
C C1 0.9318(6) 0.04268(14) 0.98206(15) 0.0177(7) Uani d . . . 1 . .
C C2 0.8204(5) 0.10124(14) 0.95474(14) 0.0145(6) Uani d . . . 1 . .
H H2 0.7941 0.1342 0.9864 0.017 Uiso calc U . R 1 . .
C C3 0.9699(5) 0.13465(14) 0.90942(14) 0.0145(6) Uani d . . . 1 . .
H H3 1.1177 0.1155 0.9127 0.017 Uiso calc U . R 1 . .
C C4 0.8679(5) 0.11312(14) 0.85047(14) 0.0149(6) Uani d . . . 1 . .
C C5 0.6264(5) 0.11784(15) 0.86237(14) 0.0151(6) Uani d . . . 1 . .
H H5A 0.5435 0.0919 0.8335 0.018 Uiso calc U . R 1 . .
H H5B 0.5771 0.1643 0.8612 0.018 Uiso calc U . R 1 . .
C C6 0.6012(5) 0.08843(14) 0.92429(15) 0.0158(6) Uani d . . . 1 . .
H H6 0.4849 0.1126 0.9455 0.019 Uiso calc U . R 1 . .
C C7 0.5458(5) 0.01688(14) 0.92116(14) 0.0169(6) Uani d . . . 1 . .
H H7 0.4211 0.0047 0.8998 0.02 Uiso calc U . R 1 . .
C C8 0.6579(5) -0.03084(14) 0.94602(14) 0.0151(6) Uani d . . . 1 . .
C C9 0.9827(5) 0.20955(14) 0.91534(14) 0.0139(6) Uani d . . . 1 . .
C C10 0.8215(5) 0.24867(14) 0.93867(14) 0.0153(6) Uani d . . . 1 . .
H H10 0.6953 0.2284 0.9536 0.018 Uiso calc U . R 1 . .
C C11 0.8408(5) 0.31754(15) 0.94065(15) 0.0177(7) Uani d . . . 1 . .
H H11 0.7289 0.3439 0.9565 0.021 Uiso calc U . R 1 . .
C C12 1.0258(5) 0.34637(14) 0.91905(14) 0.0146(6) Uani d . . . 1 . .
C C13 1.1917(5) 0.30909(15) 0.89619(14) 0.0174(7) Uani d . . . 1 . .
H H13 1.3178 0.3297 0.8815 0.021 Uiso calc U . R 1 . .
C C14 1.1702(5) 0.24084(15) 0.89512(15) 0.0177(7) Uani d . . . 1 . .
H H14 1.2848 0.2147 0.8804 0.021 Uiso calc U . R 1 . .
C C15 0.9357(5) 0.15589(14) 0.79924(14) 0.0155(6) Uani d . . . 1 . .
C C16 1.2404(6) 0.18519(15) 0.74102(15) 0.0201(7) Uani d . . . 1 . .
H H16A 1.3932 0.1942 0.7503 0.024 Uiso calc U . R 1 . .
H H16B 1.1644 0.228 0.7382 0.024 Uiso calc U . R 1 . .
C C17 1.2260(6) 0.14965(15) 0.68376(15) 0.0201(7) Uani d . . . 1 . .
C C18 1.0414(6) 0.15433(18) 0.64926(16) 0.0257(8) Uani d . . . 1 . .
H H18 0.9235 0.1805 0.6619 0.031 Uiso calc U . R 1 . .
C C19 1.0296(6) 0.12108(18) 0.59664(17) 0.0290(8) Uani d . . . 1 . .
H H19 0.903 0.124 0.5736 0.035 Uiso calc U . R 1 . .
C C20 1.2018(6) 0.08372(16) 0.57765(17) 0.0277(8) Uani d . . . 1 . .
H H20 1.1936 0.0614 0.5414 0.033 Uiso calc U . R 1 . .
C C21 1.3860(7) 0.07863(17) 0.61107(17) 0.0292(9) Uani d . . . 1 . .
H H21 1.5043 0.053 0.5979 0.035 Uiso calc U . R 1 . .
C C22 1.3965(6) 0.11142(17) 0.66424(16) 0.0244(8) Uani d . . . 1 . .
H H22 1.5223 0.1076 0.6875 0.029 Uiso calc U . R 1 . .
C C23 0.9367(5) 0.04180(14) 0.83733(14) 0.0147(6) Uani d . . . 1 . .
C C24 0.8990(7) -0.04702(18) 0.7706(2) 0.0380(11) Uani d . . . 1 . .
H H24A 0.9644 -0.0718 0.8033 0.046 Uiso calc U . R 1 . .
H H24B 1.0046 -0.045 0.7384 0.046 Uiso calc U . R 1 . .
C C25 0.6980(6) -0.08084(15) 0.75066(16) 0.0236(8) Uani d . . . 1 . .
C C26 0.6165(7) -0.13527(17) 0.77961(17) 0.0297(9) Uani d . . . 1 . .
H H26 0.6868 -0.1512 0.8135 0.036 Uiso calc U . R 1 . .
C C27 0.4315(7) -0.16707(17) 0.75940(18) 0.0326(9) Uani d . . . 1 . .
H H27 0.3773 -0.2047 0.7793 0.039 Uiso calc U . R 1 . .
C C28 0.3282(6) -0.14390(17) 0.71071(17) 0.0272(8) Uani d . . . 1 . .
H H28 0.2033 -0.1658 0.6968 0.033 Uiso calc U . R 1 . .
C C29 0.4046(6) -0.08905(17) 0.68195(17) 0.0255(8) Uani d . . . 1 . .
H H29 0.3306 -0.0726 0.6488 0.031 Uiso calc U . R 1 . .
C C30 0.5901(6) -0.05786(16) 0.70147(16) 0.0236(8) Uani d . . . 1 . .
H H30 0.6439 -0.0205 0.6811 0.028 Uiso calc U . R 1 . .
C C31 0.6151(5) -0.10256(15) 0.94156(15) 0.0178(7) Uani d . . . 1 . .
C C32 0.7762(6) -0.14832(16) 0.95238(16) 0.0220(7) Uani d . . . 1 . .
H H32 0.9144 -0.1338 0.9645 0.026 Uiso calc U . R 1 . .
C C33 0.7359(6) -0.21573(16) 0.94553(16) 0.0255(8) Uani d . . . 1 . .
H H33 0.8469 -0.2469 0.9529 0.031 Uiso calc U . R 1 . .
C C34 0.5365(6) -0.23717(16) 0.92817(16) 0.0278(8) Uani d . . . 1 . .
H H34 0.5107 -0.283 0.923 0.033 Uiso calc U . R 1 . .
C C35 0.3723(6) -0.19207(16) 0.91815(16) 0.0270(8) Uani d . . . 1 . .
H H35 0.2338 -0.2072 0.9068 0.032 Uiso calc U . R 1 . .
C C36 0.4103(5) -0.12470(15) 0.92470(15) 0.0213(7) Uani d . . . 1 . .
H H36 0.298 -0.0938 0.9178 0.026 Uiso calc U . R 1 . .
Cl Cl1 1.04957(13) 0.43206(3) 0.91983(4) 0.01984(18) Uani d . . . 1 . .
O O1 1.0973(4) 0.04820(11) 1.00814(11) 0.0256(6) Uani d . . . 1 . .
O O2 0.8425(4) -0.01856(10) 0.97916(10) 0.0175(5) Uani d . . . 1 . .
O O3 0.8211(4) 0.19375(11) 0.77431(11) 0.0227(5) Uani d . . . 1 . .
O O4 1.1445(4) 0.14550(11) 0.78770(10) 0.0174(5) Uani d . . . 1 . .
O O5 1.0609(4) 0.01034(10) 0.86659(10) 0.0197(5) Uani d . . . 1 . .
O O6 0.8416(4) 0.02009(11) 0.78948(11) 0.0245(6) Uani d . . . 1 . .


_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_site_symmetry_2
_geom_bond_distance
_geom_bond_publ_flag
C1 O1 . 1.196(4) ?
C1 O2 . 1.360(4) ?
C1 C2 . 1.510(4) ?
C2 C3 . 1.551(4) ?
C2 C6 . 1.553(4) ?
C2 H2 . 1.0 ?
C3 C9 . 1.525(4) ?
C3 C4 . 1.558(4) ?
C3 H3 . 1.0 ?
C4 C15 . 1.522(4) ?
C4 C5 . 1.529(4) ?
C4 C23 . 1.536(4) ?
C5 C6 . 1.551(4) ?
C5 H5A . 0.99 ?
C5 H5B . 0.99 ?
C6 C7 . 1.491(4) ?
C6 H6 . 1.0 ?
C7 C8 . 1.322(4) ?
C7 H7 . 0.95 ?
C8 O2 . 1.400(4) ?
C8 C31 . 1.480(4) ?
C9 C10 . 1.385(4) ?
C9 C14 . 1.405(4) ?
C10 C11 . 1.400(4) ?
C10 H10 . 0.95 ?
C11 C12 . 1.382(5) ?
C11 H11 . 0.95 ?
C12 C13 . 1.381(4) ?
C12 Cl1 . 1.741(3) ?
C13 C14 . 1.388(4) ?
C13 H13 . 0.95 ?
C14 H14 . 0.95 ?
C15 O3 . 1.193(4) ?
C15 O4 . 1.341(4) ?
C16 O4 . 1.467(4) ?
C16 C17 . 1.503(5) ?
C16 H16A . 0.99 ?
C16 H16B . 0.99 ?
C17 C22 . 1.387(5) ?
C17 C18 . 1.398(5) ?
C18 C19 . 1.386(5) ?
C18 H18 . 0.95 ?
C19 C20 . 1.381(5) ?
C19 H19 . 0.95 ?
C20 C21 . 1.383(6) ?
C20 H20 . 0.95 ?
C21 C22 . 1.392(5) ?
C21 H21 . 0.95 ?
C22 H22 . 0.95 ?
C23 O5 . 1.206(4) ?
C23 O6 . 1.324(4) ?
C24 O6 . 1.470(4) ?
C24 C25 . 1.496(5) ?
C24 H24A . 0.99 ?
C24 H24B . 0.99 ?
C25 C26 . 1.384(5) ?
C25 C30 . 1.395(5) ?
C26 C27 . 1.397(6) ?
C26 H26 . 0.95 ?
C27 C28 . 1.373(5) ?
C27 H27 . 0.95 ?
C28 C29 . 1.377(5) ?
C28 H28 . 0.95 ?
C29 C30 . 1.389(5) ?
C29 H29 . 0.95 ?
C30 H30 . 0.95 ?
C31 C32 . 1.386(5) ?
C31 C36 . 1.405(5) ?
C32 C33 . 1.396(4) ?
C32 H32 . 0.95 ?
C33 C34 . 1.373(5) ?
C33 H33 . 0.95 ?
C34 C35 . 1.389(5) ?
C34 H34 . 0.95 ?
C35 C36 . 1.393(4) ?
C35 H35 . 0.95 ?
C36 H36 . 0.95 ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle
_geom_angle_publ_flag
O1 C1 O2 . . 117.4(3) ?
O1 C1 C2 . . 122.0(3) ?
O2 C1 C2 . . 120.6(3) ?
C1 C2 C3 . . 110.3(3) ?
C1 C2 C6 . . 117.3(2) ?
C3 C2 C6 . . 107.2(3) ?
C1 C2 H2 . . 107.2 ?
C3 C2 H2 . . 107.2 ?
C6 C2 H2 . . 107.2 ?
C9 C3 C2 . . 113.9(2) ?
C9 C3 C4 . . 112.2(3) ?
C2 C3 C4 . . 102.6(2) ?
C9 C3 H3 . . 109.3 ?
C2 C3 H3 . . 109.3 ?
C4 C3 H3 . . 109.3 ?
C15 C4 C5 . . 112.0(3) ?
C15 C4 C23 . . 107.8(2) ?
C5 C4 C23 . . 111.6(3) ?
C15 C4 C3 . . 113.7(2) ?
C5 C4 C3 . . 103.1(3) ?
C23 C4 C3 . . 108.7(3) ?
C4 C5 C6 . . 103.8(3) ?
C4 C5 H5A . . 111.0 ?
C6 C5 H5A . . 111.0 ?
C4 C5 H5B . . 111.0 ?
C6 C5 H5B . . 111.0 ?
H5A C5 H5B . . 109.0 ?
C7 C6 C5 . . 110.6(3) ?
C7 C6 C2 . . 112.7(2) ?
C5 C6 C2 . . 105.1(2) ?
C7 C6 H6 . . 109.4 ?
C5 C6 H6 . . 109.4 ?
C2 C6 H6 . . 109.4 ?
C8 C7 C6 . . 124.6(3) ?
C8 C7 H7 . . 117.7 ?
C6 C7 H7 . . 117.7 ?
C7 C8 O2 . . 122.5(3) ?
C7 C8 C31 . . 126.4(3) ?
O2 C8 C31 . . 111.1(3) ?
C10 C9 C14 . . 118.0(3) ?
C10 C9 C3 . . 124.4(3) ?
C14 C9 C3 . . 117.5(3) ?
C9 C10 C11 . . 121.3(3) ?
C9 C10 H10 . . 119.3 ?
C11 C10 H10 . . 119.3 ?
C12 C11 C10 . . 118.7(3) ?
C12 C11 H11 . . 120.7 ?
C10 C11 H11 . . 120.7 ?
C13 C12 C11 . . 121.8(3) ?
C13 C12 Cl1 . . 119.0(2) ?
C11 C12 Cl1 . . 119.2(2) ?
C12 C13 C14 . . 118.6(3) ?
C12 C13 H13 . . 120.7 ?
C14 C13 H13 . . 120.7 ?
C13 C14 C9 . . 121.5(3) ?
C13 C14 H14 . . 119.3 ?
C9 C14 H14 . . 119.3 ?
O3 C15 O4 . . 125.7(3) ?
O3 C15 C4 . . 124.9(3) ?
O4 C15 C4 . . 109.4(3) ?
O4 C16 C17 . . 110.7(2) ?
O4 C16 H16A . . 109.5 ?
C17 C16 H16A . . 109.5 ?
O4 C16 H16B . . 109.5 ?
C17 C16 H16B . . 109.5 ?
H16A C16 H16B . . 108.1 ?
C22 C17 C18 . . 118.8(3) ?
C22 C17 C16 . . 120.3(3) ?
C18 C17 C16 . . 120.9(3) ?
C19 C18 C17 . . 120.4(4) ?
C19 C18 H18 . . 119.8 ?
C17 C18 H18 . . 119.8 ?
C20 C19 C18 . . 120.0(4) ?
C20 C19 H19 . . 120.0 ?
C18 C19 H19 . . 120.0 ?
C19 C20 C21 . . 120.5(3) ?
C19 C20 H20 . . 119.8 ?
C21 C20 H20 . . 119.8 ?
C20 C21 C22 . . 119.4(4) ?
C20 C21 H21 . . 120.3 ?
C22 C21 H21 . . 120.3 ?
C17 C22 C21 . . 120.9(4) ?
C17 C22 H22 . . 119.5 ?
C21 C22 H22 . . 119.5 ?
O5 C23 O6 . . 125.0(3) ?
O5 C23 C4 . . 124.4(3) ?
O6 C23 C4 . . 110.6(3) ?
O6 C24 C25 . . 108.1(3) ?
O6 C24 H24A . . 110.1 ?
C25 C24 H24A . . 110.1 ?
O6 C24 H24B . . 110.1 ?
C25 C24 H24B . . 110.1 ?
H24A C24 H24B . . 108.4 ?
C26 C25 C30 . . 118.6(3) ?
C26 C25 C24 . . 121.5(4) ?
C30 C25 C24 . . 119.8(3) ?
C25 C26 C27 . . 120.6(4) ?
C25 C26 H26 . . 119.7 ?
C27 C26 H26 . . 119.7 ?
C28 C27 C26 . . 119.9(4) ?
C28 C27 H27 . . 120.1 ?
C26 C27 H27 . . 120.1 ?
C27 C28 C29 . . 120.4(4) ?
C27 C28 H28 . . 119.8 ?
C29 C28 H28 . . 119.8 ?
C28 C29 C30 . . 119.8(4) ?
C28 C29 H29 . . 120.1 ?
C30 C29 H29 . . 120.1 ?
C29 C30 C25 . . 120.6(3) ?
C29 C30 H30 . . 119.7 ?
C25 C30 H30 . . 119.7 ?
C32 C31 C36 . . 119.4(3) ?
C32 C31 C8 . . 120.9(3) ?
C36 C31 C8 . . 119.7(3) ?
C31 C32 C33 . . 120.2(3) ?
C31 C32 H32 . . 119.9 ?
C33 C32 H32 . . 119.9 ?
C34 C33 C32 . . 120.3(3) ?
C34 C33 H33 . . 119.9 ?
C32 C33 H33 . . 119.9 ?
C33 C34 C35 . . 120.3(3) ?
C33 C34 H34 . . 119.9 ?
C35 C34 H34 . . 119.9 ?
C34 C35 C36 . . 120.1(3) ?
C34 C35 H35 . . 119.9 ?
C36 C35 H35 . . 119.9 ?
C35 C36 C31 . . 119.7(3) ?
C35 C36 H36 . . 120.1 ?
C31 C36 H36 . . 120.1 ?
C1 O2 C8 . . 121.5(2) ?
C15 O4 C16 . . 116.9(3) ?
C23 O6 C24 . . 116.3(3) ?



