# 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/. 
# 
# Audit and citation data items have may 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_jbs10
_audit_block_doi                 10.5517/ccykfqm
_database_code_depnum_ccdc_archive 'CCDC 880701'
loop_
_citation_id
_citation_doi
_citation_year
1 10.1021/ja3015764 2012
_audit_update_record             
;
2012-05-08 deposited with the CCDC.
2014-11-20 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C36 H58 Cl N3 O2'
_chemical_formula_weight         600.30
_chemical_absolute_configuration ad

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'
N N 0.0061 0.0033 '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'

_symmetry_cell_setting           Trigonal
_symmetry_space_group_name_H-M   P3(2)

loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-y, x-y, z+2/3'
'-x+y, -x, z+1/3'

_cell_length_a                   15.8650(10)
_cell_length_b                   15.8650(10)
_cell_length_c                   11.7214(8)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                120.00
_cell_volume                     2555.0(3)
_cell_formula_units_Z            3
_cell_measurement_temperature    150(2)
_cell_measurement_reflns_used    9941
_cell_measurement_theta_min      2.28
_cell_measurement_theta_max      31.79

_exptl_crystal_description       BLOCK
_exptl_crystal_colour            COLORLESS
_exptl_crystal_size_max          0.36
_exptl_crystal_size_mid          0.36
_exptl_crystal_size_min          0.36
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.170
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             984
_exptl_absorpt_coefficient_mu    0.147
_exptl_absorpt_correction_type   EMPIRICAL
_exptl_absorpt_correction_T_min  0.9490
_exptl_absorpt_correction_T_max  0.9490
_exptl_absorpt_process_details   SADABS

_exptl_special_details           
;
?
;

_diffrn_ambient_temperature      150(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  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            44296
_diffrn_reflns_av_R_equivalents  0.0294
_diffrn_reflns_av_sigmaI/netI    0.0305
_diffrn_reflns_limit_h_min       -23
_diffrn_reflns_limit_h_max       23
_diffrn_reflns_limit_k_min       -23
_diffrn_reflns_limit_k_max       23
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_theta_min         1.48
_diffrn_reflns_theta_max         31.96
_reflns_number_total             11637
_reflns_number_gt                9620
_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.

O2 is refined as an oxygen atom based on the synthetic chemists
experimental procedure which used H2O. However, the hydrogen atoms on O2
were not located or refined.
;

_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)+(0.0698P)²+0.1617P] 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_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.01(4)
_refine_ls_number_reflns         11637
_refine_ls_number_parameters     381
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0598
_refine_ls_R_factor_gt           0.0448
_refine_ls_wR_factor_ref         0.1195
_refine_ls_wR_factor_gt          0.1095
_refine_ls_goodness_of_fit_ref   1.015
_refine_ls_restrained_S_all      1.015
_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 0.76815(10) 0.38930(10) 0.21305(12) 0.0445(3) Uani 1 1 d . . .
H1A H 0.8141 0.4421 0.1884 0.067 Uiso 1 1 calc R . .
N1 N 0.93653(8) 0.36825(8) 0.25000(10) 0.0255(2) Uani 1 1 d . . .
H1B H 0.9858 0.4206 0.2799 0.031 Uiso 1 1 calc R . .
N2 N 0.82798(8) 0.21424(9) -0.00082(11) 0.0270(2) Uani 1 1 d . . .
N3 N 1.09847(8) 0.38564(9) 0.02062(10) 0.0253(2) Uani 1 1 d . . .
C1 C 0.94704(9) 0.34157(9) 0.14659(12) 0.0230(2) Uani 1 1 d . . .
C2 C 0.90784(9) 0.28259(9) 0.05148(11) 0.0228(2) Uani 1 1 d . . .
C3 C 1.00779(9) 0.34760(9) 0.05821(11) 0.0228(2) Uani 1 1 d . . .
C11 C 0.79159(12) 0.37076(13) 0.32261(16) 0.0377(3) Uani 1 1 d . . .
H11A H 0.7309 0.3322 0.3668 0.045 Uiso 1 1 calc R . .
H11B H 0.8316 0.4333 0.3629 0.045 Uiso 1 1 calc R . .
C12 C 0.84736(10) 0.31550(10) 0.31745(12) 0.0281(3) Uani 1 1 d . . .
H12A H 0.8048 0.2510 0.2805 0.034 Uiso 1 1 calc R . .
C13 C 0.87364(12) 0.29791(12) 0.43719(13) 0.0351(3) Uani 1 1 d . . .
H13A H 0.9161 0.3615 0.4742 0.042 Uiso 1 1 calc R . .
H13B H 0.8134 0.2632 0.4831 0.042 Uiso 1 1 calc R . .
C14 C 0.92484(12) 0.23952(12) 0.43709(12) 0.0332(3) Uani 1 1 d . . .
C15 C 0.87823(13) 0.14417(13) 0.39855(15) 0.0379(3) Uani 1 1 d . . .
H15A H 0.8132 0.1156 0.3714 0.046 Uiso 1 1 calc R . .
C16 C 0.92437(15) 0.08966(15) 0.39871(18) 0.0472(4) Uani 1 1 d . . .
H16A H 0.8911 0.0245 0.3716 0.057 Uiso 1 1 calc R . .
C17 C 1.01917(15) 0.12998(17) 0.43845(17) 0.0488(5) Uani 1 1 d . . .
H17A H 1.0510 0.0928 0.4391 0.059 Uiso 1 1 calc R . .
C18 C 1.06625(14) 0.22429(17) 0.47678(16) 0.0492(5) Uani 1 1 d . . .
H18A H 1.1311 0.2523 0.5043 0.059 Uiso 1 1 calc R . .
C19 C 1.02048(13) 0.27906(14) 0.47580(14) 0.0418(4) Uani 1 1 d . . .
H19A H 1.0546 0.3445 0.5018 0.050 Uiso 1 1 calc R . .
C21 C 0.73470(9) 0.18740(10) 0.05608(12) 0.0251(2) Uani 1 1 d . . .
H21A H 0.7478 0.2418 0.1094 0.030 Uiso 1 1 calc R . .
C22 C 0.69850(11) 0.09572(11) 0.12924(14) 0.0309(3) Uani 1 1 d . . .
H22A H 0.7501 0.1045 0.1835 0.037 Uiso 1 1 calc R . .
H22B H 0.6836 0.0394 0.0797 0.037 Uiso 1 1 calc R . .
C23 C 0.60643(12) 0.07564(13) 0.19570(16) 0.0397(4) Uani 1 1 d . . .
H23A H 0.5811 0.0138 0.2384 0.048 Uiso 1 1 calc R . .
H23B H 0.6232 0.1285 0.2515 0.048 Uiso 1 1 calc R . .
C24 C 0.52863(12) 0.06915(14) 0.11514(17) 0.0428(4) Uani 1 1 d . . .
H24A H 0.4719 0.0606 0.1598 0.051 Uiso 1 1 calc R . .
H24B H 0.5066 0.0117 0.0650 0.051 Uiso 1 1 calc R . .
C25 C 0.56730(11) 0.16057(14) 0.04227(14) 0.0358(3) Uani 1 1 d . . .
H25A H 0.5849 0.2174 0.0921 0.043 Uiso 1 1 calc R . .
H25B H 0.5156 0.1539 -0.0106 0.043 Uiso 1 1 calc R . .
C26 C 0.65621(11) 0.17798(12) -0.02623(13) 0.0317(3) Uani 1 1 d . . .
H26A H 0.6385 0.1229 -0.0791 0.038 Uiso 1 1 calc R . .
H26B H 0.6807 0.2382 -0.0719 0.038 Uiso 1 1 calc R . .
C31 C 0.83107(11) 0.14536(10) -0.08295(12) 0.0279(3) Uani 1 1 d . . .
H31A H 0.7674 0.0835 -0.0756 0.034 Uiso 1 1 calc R . .
C32 C 0.83812(13) 0.17725(12) -0.20628(13) 0.0355(3) Uani 1 1 d . . .
H32A H 0.9004 0.2385 -0.2186 0.043 Uiso 1 1 calc R . .
H32B H 0.7842 0.1897 -0.2237 0.043 Uiso 1 1 calc R . .
C33 C 0.83255(14) 0.09817(13) -0.28566(14) 0.0396(4) Uani 1 1 d . . .
H33A H 0.7672 0.0396 -0.2795 0.048 Uiso 1 1 calc R . .
H33B H 0.8416 0.1215 -0.3655 0.048 Uiso 1 1 calc R . .
C34 C 0.90914(15) 0.07113(14) -0.25698(17) 0.0445(4) Uani 1 1 d . . .
H34A H 0.8990 0.0158 -0.3055 0.053 Uiso 1 1 calc R . .
H34B H 0.9743 0.1269 -0.2748 0.053 Uiso 1 1 calc R . .
C35 C 0.90655(12) 0.04362(12) -0.13353(16) 0.0374(3) Uani 1 1 d . . .
H35A H 0.9630 0.0349 -0.1174 0.045 Uiso 1 1 calc R . .
H35B H 0.8466 -0.0193 -0.1192 0.045 Uiso 1 1 calc R . .
C36 C 0.90907(11) 0.12036(11) -0.05301(13) 0.0298(3) Uani 1 1 d . . .
H36A H 0.8992 0.0958 0.0263 0.036 Uiso 1 1 calc R . .
H36B H 0.9738 0.1799 -0.0573 0.036 Uiso 1 1 calc R . .
C41 C 1.11863(9) 0.38049(10) -0.10113(12) 0.0238(2) Uani 1 1 d . . .
H41A H 1.0546 0.3429 -0.1410 0.029 Uiso 1 1 calc R . .
C42 C 1.17195(12) 0.48180(11) -0.15404(14) 0.0326(3) Uani 1 1 d . . .
H42A H 1.2354 0.5213 -0.1154 0.039 Uiso 1 1 calc R . .
H42B H 1.1332 0.5143 -0.1428 0.039 Uiso 1 1 calc R . .
C43 C 1.18852(16) 0.47575(13) -0.28139(15) 0.0441(4) Uani 1 1 d . . .
H43A H 1.1249 0.4418 -0.3209 0.053 Uiso 1 1 calc R . .
H43B H 1.2259 0.5423 -0.3132 0.053 Uiso 1 1 calc R . .
C44 C 1.24318(14) 0.42216(12) -0.30294(17) 0.0440(4) Uani 1 1 d . . .
H44A H 1.3096 0.4599 -0.2708 0.053 Uiso 1 1 calc R . .
H44B H 1.2491 0.4158 -0.3862 0.053 Uiso 1 1 calc R . .
C45 C 1.19124(12) 0.32213(12) -0.24919(15) 0.0354(3) Uani 1 1 d . . .
H45A H 1.2301 0.2898 -0.2613 0.043 Uiso 1 1 calc R . .
H45B H 1.1274 0.2823 -0.2869 0.043 Uiso 1 1 calc R . .
C46 C 1.17555(11) 0.32749(11) -0.12142(14) 0.0300(3) Uani 1 1 d . . .
H46A H 1.2393 0.3626 -0.0823 0.036 Uiso 1 1 calc R . .
H46B H 1.1391 0.2609 -0.0894 0.036 Uiso 1 1 calc R . .
C51 C 1.17954(9) 0.43225(10) 0.10359(12) 0.0246(2) Uani 1 1 d . . .
H51A H 1.2411 0.4494 0.0619 0.029 Uiso 1 1 calc R . .
C52 C 1.16658(11) 0.35961(11) 0.19668(14) 0.0307(3) Uani 1 1 d . . .
H52A H 1.1647 0.3019 0.1616 0.037 Uiso 1 1 calc R . .
H52B H 1.1038 0.3377 0.2362 0.037 Uiso 1 1 calc R . .
C53 C 1.24932(12) 0.40478(14) 0.28329(15) 0.0382(4) Uani 1 1 d . . .
H53A H 1.2371 0.3574 0.3450 0.046 Uiso 1 1 calc R . .
H53B H 1.3113 0.4205 0.2455 0.046 Uiso 1 1 calc R . .
C54 C 1.25772(13) 0.49656(14) 0.33389(15) 0.0429(4) Uani 1 1 d . . .
H54A H 1.1976 0.4801 0.3766 0.052 Uiso 1 1 calc R . .
H54B H 1.3130 0.5258 0.3881 0.052 Uiso 1 1 calc R . .
C55 C 1.27340(13) 0.56936(12) 0.24100(16) 0.0424(4) Uani 1 1 d . . .
H55A H 1.3361 0.5894 0.2021 0.051 Uiso 1 1 calc R . .
H55B H 1.2770 0.6280 0.2756 0.051 Uiso 1 1 calc R . .
C56 C 1.19052(11) 0.52586(10) 0.15304(14) 0.0310(3) Uani 1 1 d . . .
H56A H 1.1288 0.5122 0.1900 0.037 Uiso 1 1 calc R . .
H56B H 1.2046 0.5734 0.0909 0.037 Uiso 1 1 calc R . .
Cl Cl 1.04713(4) 0.57032(3) 0.37761(4) 0.04757(11) Uani 1 1 d . . .
O2 O 0.93111(13) 0.57236(12) 0.17096(17) 0.0663(4) 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
O1 C11 1.408(2) . ?
N1 C1 1.3217(18) . ?
N1 C12 1.4638(18) . ?
N2 C2 1.3354(17) . ?
N2 C31 1.4754(18) . ?
N2 C21 1.4785(17) . ?
N3 C3 1.3266(17) . ?
N3 C41 1.4737(18) . ?
N3 C51 1.4818(17) . ?
C1 C3 1.3852(18) . ?
C1 C2 1.3867(18) . ?
C2 C3 1.3960(18) . ?
C11 C12 1.527(2) . ?
C12 C13 1.529(2) . ?
C13 C14 1.507(3) . ?
C14 C15 1.386(2) . ?
C14 C19 1.396(2) . ?
C15 C16 1.384(3) . ?
C16 C17 1.388(3) . ?
C17 C18 1.371(3) . ?
C18 C19 1.383(3) . ?
C21 C26 1.522(2) . ?
C21 C22 1.531(2) . ?
C22 C23 1.542(2) . ?
C23 C24 1.516(3) . ?
C24 C25 1.523(3) . ?
C25 C26 1.523(2) . ?
C31 C36 1.517(2) . ?
C31 C32 1.517(2) . ?
C32 C33 1.529(2) . ?
C33 C34 1.515(3) . ?
C34 C35 1.506(3) . ?
C35 C36 1.525(2) . ?
C41 C42 1.5243(19) . ?
C41 C46 1.5292(19) . ?
C42 C43 1.527(2) . ?
C43 C44 1.509(3) . ?
C44 C45 1.512(2) . ?
C45 C46 1.527(2) . ?
C51 C56 1.521(2) . ?
C51 C52 1.524(2) . ?
C52 C53 1.525(2) . ?
C53 C54 1.515(3) . ?
C54 C55 1.515(3) . ?
C55 C56 1.537(2) . ?

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 N1 C12 123.57(11) . . ?
C2 N2 C31 122.11(11) . . ?
C2 N2 C21 115.69(11) . . ?
C31 N2 C21 118.70(11) . . ?
C3 N3 C41 120.83(11) . . ?
C3 N3 C51 118.84(11) . . ?
C41 N3 C51 120.33(10) . . ?
N1 C1 C3 149.15(12) . . ?
N1 C1 C2 150.17(13) . . ?
C3 C1 C2 60.48(9) . . ?
N2 C2 C1 147.17(13) . . ?
N2 C2 C3 153.12(13) . . ?
C1 C2 C3 59.71(9) . . ?
N3 C3 C1 146.99(13) . . ?
N3 C3 C2 152.89(13) . . ?
C1 C3 C2 59.81(9) . . ?
O1 C11 C12 111.92(13) . . ?
N1 C12 C11 111.41(12) . . ?
N1 C12 C13 109.05(12) . . ?
C11 C12 C13 110.96(12) . . ?
C14 C13 C12 113.05(12) . . ?
C15 C14 C19 117.59(17) . . ?
C15 C14 C13 120.93(15) . . ?
C19 C14 C13 121.48(15) . . ?
C16 C15 C14 121.42(17) . . ?
C15 C16 C17 120.14(19) . . ?
C18 C17 C16 119.11(19) . . ?
C17 C18 C19 120.79(18) . . ?
C18 C19 C14 120.95(18) . . ?
N2 C21 C26 113.22(12) . . ?
N2 C21 C22 111.85(12) . . ?
C26 C21 C22 111.21(12) . . ?
C21 C22 C23 110.24(12) . . ?
C24 C23 C22 110.75(14) . . ?
C23 C24 C25 110.98(14) . . ?
C24 C25 C26 111.34(14) . . ?
C21 C26 C25 108.76(12) . . ?
N2 C31 C36 112.10(12) . . ?
N2 C31 C32 113.51(12) . . ?
C36 C31 C32 111.95(13) . . ?
C31 C32 C33 109.99(13) . . ?
C34 C33 C32 111.84(14) . . ?
C35 C34 C33 112.69(14) . . ?
C34 C35 C36 112.16(14) . . ?
C31 C36 C35 111.49(12) . . ?
N3 C41 C42 110.91(11) . . ?
N3 C41 C46 112.66(12) . . ?
C42 C41 C46 110.34(11) . . ?
C41 C42 C43 110.71(13) . . ?
C44 C43 C42 111.38(15) . . ?
C43 C44 C45 110.89(14) . . ?
C44 C45 C46 111.62(13) . . ?
C45 C46 C41 109.91(13) . . ?
N3 C51 C56 112.60(11) . . ?
N3 C51 C52 109.70(11) . . ?
C56 C51 C52 111.82(12) . . ?
C51 C52 C53 111.23(12) . . ?
C54 C53 C52 110.70(13) . . ?
C55 C54 C53 110.70(15) . . ?
C54 C55 C56 111.25(13) . . ?
C51 C56 C55 110.41(13) . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
O1 H1A O2 0.84 1.98 2.802(2) 165.8 .
N1 H1B Cl 0.88 2.36 3.1572(12) 150.0 .

_diffrn_measured_fraction_theta_max 0.995
_diffrn_reflns_theta_full        31.96
_diffrn_measured_fraction_theta_full 0.995
_refine_diff_density_max         0.423
_refine_diff_density_min         -0.159
_refine_diff_density_rms         0.044
