# Electronic Supplementary Material (ESI) for Organic & Biomolecular Chemistry.
# This journal is © The Royal Society of Chemistry 2016

####################################################################### 
# 
# 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_s2318b
_database_code_depnum_ccdc_archive 'CCDC 1473670'
_audit_update_record             
;
2016-04-12 deposited with the CCDC.
2016-05-23 downloaded from the CCDC.
;
_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C48 H76'
_chemical_formula_weight         653.09

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'

_symmetry_cell_setting           Monoclinic
_symmetry_space_group_name_H-M   P2(1)/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                   17.926(12)
_cell_length_b                   14.393(10)
_cell_length_c                   8.191(6)
_cell_angle_alpha                90.00
_cell_angle_beta                 93.891(14)
_cell_angle_gamma                90.00
_cell_volume                     2109(3)
_cell_formula_units_Z            2
_cell_measurement_temperature    230(2)
_cell_measurement_reflns_used    2386
_cell_measurement_theta_min      2.28
_cell_measurement_theta_max      26.24

_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.60
_exptl_crystal_size_mid          0.60
_exptl_crystal_size_min          0.60
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.029
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             728
_exptl_absorpt_coefficient_mu    0.057
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.9667
_exptl_absorpt_correction_T_max  0.9667
_exptl_absorpt_process_details   TWINABS

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      230(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            6592
_diffrn_reflns_av_R_equivalents  0.0000
_diffrn_reflns_av_sigmaI/netI    0.0290
_diffrn_reflns_limit_h_min       0
_diffrn_reflns_limit_h_max       21
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_k_max       0
_diffrn_reflns_limit_l_min       -9
_diffrn_reflns_limit_l_max       9
_diffrn_reflns_theta_min         1.82
_diffrn_reflns_theta_max         25.03
_reflns_number_total             6592
_reflns_number_gt                4726
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Bruker SMART'
_computing_cell_refinement       'Bruker SMART'
_computing_data_reduction        'Bruker SAINT'
_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          Twin

_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)+(0.1064P)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     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         6592
_refine_ls_number_parameters     220
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0719
_refine_ls_R_factor_gt           0.0538
_refine_ls_wR_factor_ref         0.1546
_refine_ls_wR_factor_gt          0.1449
_refine_ls_goodness_of_fit_ref   0.958
_refine_ls_restrained_S_all      0.958
_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
C1 C 0.48750(7) 0.36490(8) 0.51230(15) 0.0371(3) Uani 1 1 d . . .
C2 C 0.55606(7) 0.37626(8) 0.44455(15) 0.0395(3) Uani 1 1 d . . .
H2 H 0.5977 0.3414 0.4886 0.047 Uiso 1 1 calc R . .
C3 C 0.56620(7) 0.43667(8) 0.31470(15) 0.0379(3) Uani 1 1 d . . .
C4 C 0.50512(7) 0.49088(9) 0.25840(13) 0.0373(3) Uani 1 1 d . . .
C5 C 0.43481(7) 0.46211(9) 0.29869(14) 0.0393(3) Uani 1 1 d . . .
H5 H 0.3921 0.4875 0.2396 0.047 Uiso 1 1 calc R . .
C6 C 0.42398(6) 0.39775(8) 0.42180(14) 0.0359(3) Uani 1 1 d . . .
C7 C 0.48349(7) 0.34216(9) 0.69078(16) 0.0434(3) Uani 1 1 d . . .
H7 H 0.4798 0.2794 0.7255 0.052 Uiso 1 1 calc R . .
C8 C 0.48517(7) 0.41135(10) 0.80001(16) 0.0443(3) Uani 1 1 d . . .
H8 H 0.4803 0.3988 0.9126 0.053 Uiso 1 1 calc R . .
C9 C 0.64138(7) 0.44677(9) 0.24550(15) 0.0427(3) Uani 1 1 d . . .
H9A H 0.6810 0.4383 0.3344 0.051 Uiso 1 1 calc R . .
H9B H 0.6461 0.5104 0.2015 0.051 Uiso 1 1 calc R . .
C10 C 0.65298(7) 0.37667(9) 0.11001(15) 0.0403(3) Uani 1 1 d . . .
H10A H 0.6513 0.3133 0.1565 0.048 Uiso 1 1 calc R . .
H10B H 0.6111 0.3823 0.0255 0.048 Uiso 1 1 calc R . .
C11 C 0.72591(7) 0.38837(9) 0.02890(16) 0.0432(3) Uani 1 1 d . . .
H11A H 0.7679 0.3828 0.1133 0.052 Uiso 1 1 calc R . .
H11B H 0.7276 0.4517 -0.0181 0.052 Uiso 1 1 calc R . .
C12 C 0.73685(8) 0.31805(9) -0.10549(17) 0.0489(4) Uani 1 1 d . . .
H12A H 0.6931 0.3211 -0.1859 0.059 Uiso 1 1 calc R . .
H12B H 0.7378 0.2551 -0.0567 0.059 Uiso 1 1 calc R . .
C13 C 0.80754(8) 0.33120(10) -0.19603(17) 0.0525(4) Uani 1 1 d . . .
H13A H 0.8507 0.3366 -0.1144 0.063 Uiso 1 1 calc R . .
H13B H 0.8153 0.2749 -0.2623 0.063 Uiso 1 1 calc R . .
C14 C 0.80692(8) 0.41553(10) -0.30797(18) 0.0547(4) Uani 1 1 d . . .
H14A H 0.7616 0.4129 -0.3838 0.066 Uiso 1 1 calc R . .
H14B H 0.8035 0.4722 -0.2405 0.066 Uiso 1 1 calc R . .
C15 C 0.87438(10) 0.42374(12) -0.4072(2) 0.0703(5) Uani 1 1 d . . .
H15A H 0.8791 0.3659 -0.4712 0.084 Uiso 1 1 calc R . .
H15B H 0.9196 0.4290 -0.3313 0.084 Uiso 1 1 calc R . .
C16 C 0.87237(10) 0.50550(13) -0.5236(2) 0.0812(5) Uani 1 1 d . . .
H16A H 0.8284 0.5004 -0.6011 0.122 Uiso 1 1 calc R . .
H16B H 0.9178 0.5056 -0.5838 0.122 Uiso 1 1 calc R . .
H16C H 0.8696 0.5634 -0.4614 0.122 Uiso 1 1 calc R . .
C17 C 0.34645(7) 0.37301(8) 0.46624(16) 0.0391(3) Uani 1 1 d . . .
H17A H 0.3100 0.4120 0.4011 0.047 Uiso 1 1 calc R . .
H17B H 0.3418 0.3877 0.5832 0.047 Uiso 1 1 calc R . .
C18 C 0.32671(6) 0.27140(8) 0.43729(15) 0.0385(3) Uani 1 1 d . . .
H18A H 0.3372 0.2544 0.3240 0.046 Uiso 1 1 calc R . .
H18B H 0.3589 0.2325 0.5128 0.046 Uiso 1 1 calc R . .
C19 C 0.24555(6) 0.25066(8) 0.46286(15) 0.0377(3) Uani 1 1 d . . .
H19A H 0.2136 0.2839 0.3785 0.045 Uiso 1 1 calc R . .
H19B H 0.2336 0.2749 0.5711 0.045 Uiso 1 1 calc R . .
C20 C 0.22679(7) 0.14797(9) 0.45448(17) 0.0469(3) Uani 1 1 d . . .
H20A H 0.2494 0.1210 0.3583 0.056 Uiso 1 1 calc R . .
H20B H 0.2503 0.1173 0.5532 0.056 Uiso 1 1 calc R . .
C21 C 0.14413(8) 0.12535(10) 0.44264(18) 0.0523(4) Uani 1 1 d . . .
H21A H 0.1216 0.1501 0.3378 0.063 Uiso 1 1 calc R . .
H21B H 0.1382 0.0570 0.4398 0.063 Uiso 1 1 calc R . .
C22 C 0.10110(7) 0.16312(10) 0.57966(18) 0.0521(4) Uani 1 1 d . . .
H22A H 0.1018 0.2318 0.5743 0.062 Uiso 1 1 calc R . .
H22B H 0.1271 0.1446 0.6852 0.062 Uiso 1 1 calc R . .
C23 C 0.02074(8) 0.13104(12) 0.5775(2) 0.0648(4) Uani 1 1 d . . .
H23A H -0.0048 0.1473 0.4703 0.078 Uiso 1 1 calc R . .
H23B H 0.0200 0.0625 0.5876 0.078 Uiso 1 1 calc R . .
C24 C -0.02234(10) 0.17189(15) 0.7102(3) 0.0887(6) Uani 1 1 d . . .
H24A H 0.0017 0.1549 0.8170 0.133 Uiso 1 1 calc R . .
H24B H -0.0736 0.1479 0.7011 0.133 Uiso 1 1 calc R . .
H24C H -0.0233 0.2397 0.6994 0.133 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
C1 C2 1.3921(18) . ?
C1 C6 1.3981(18) . ?
C1 C7 1.505(2) . ?
C2 C3 1.3951(18) . ?
C2 H2 0.9500 . ?
C3 C4 1.3970(18) . ?
C3 C9 1.5043(18) . ?
C4 C5 1.3876(18) . ?
C4 C8 1.500(2) 3_666 ?
C5 C6 1.3925(18) . ?
C5 H5 0.9500 . ?
C6 C17 1.5033(18) . ?
C7 C8 1.338(2) . ?
C7 H7 0.9500 . ?
C8 C4 1.500(2) 3_666 ?
C8 H8 0.9500 . ?
C9 C10 1.5246(18) . ?
C9 H9A 0.9900 . ?
C9 H9B 0.9900 . ?
C10 C11 1.5156(18) . ?
C10 H10A 0.9900 . ?
C10 H10B 0.9900 . ?
C11 C12 1.5179(19) . ?
C11 H11A 0.9900 . ?
C11 H11B 0.9900 . ?
C12 C13 1.523(2) . ?
C12 H12A 0.9900 . ?
C12 H12B 0.9900 . ?
C13 C14 1.521(2) . ?
C13 H13A 0.9900 . ?
C13 H13B 0.9900 . ?
C14 C15 1.507(2) . ?
C14 H14A 0.9900 . ?
C14 H14B 0.9900 . ?
C15 C16 1.513(2) . ?
C15 H15A 0.9900 . ?
C15 H15B 0.9900 . ?
C16 H16A 0.9800 . ?
C16 H16B 0.9800 . ?
C16 H16C 0.9800 . ?
C17 C18 1.5194(19) . ?
C17 H17A 0.9900 . ?
C17 H17B 0.9900 . ?
C18 C19 1.5136(18) . ?
C18 H18A 0.9900 . ?
C18 H18B 0.9900 . ?
C19 C20 1.5163(19) . ?
C19 H19A 0.9900 . ?
C19 H19B 0.9900 . ?
C20 C21 1.514(2) . ?
C20 H20A 0.9900 . ?
C20 H20B 0.9900 . ?
C21 C22 1.506(2) . ?
C21 H21A 0.9900 . ?
C21 H21B 0.9900 . ?
C22 C23 1.512(2) . ?
C22 H22A 0.9900 . ?
C22 H22B 0.9900 . ?
C23 C24 1.496(2) . ?
C23 H23A 0.9900 . ?
C23 H23B 0.9900 . ?
C24 H24A 0.9800 . ?
C24 H24B 0.9800 . ?
C24 H24C 0.9800 . ?

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
C2 C1 C6 117.27(12) . . ?
C2 C1 C7 120.97(11) . . ?
C6 C1 C7 119.86(11) . . ?
C1 C2 C3 122.77(12) . . ?
C1 C2 H2 118.6 . . ?
C3 C2 H2 118.6 . . ?
C2 C3 C4 117.39(11) . . ?
C2 C3 C9 120.92(11) . . ?
C4 C3 C9 121.59(12) . . ?
C5 C4 C3 117.32(12) . . ?
C5 C4 C8 118.87(11) . 3_666 ?
C3 C4 C8 121.59(11) . 3_666 ?
C4 C5 C6 122.97(11) . . ?
C4 C5 H5 118.5 . . ?
C6 C5 H5 118.5 . . ?
C5 C6 C1 117.41(11) . . ?
C5 C6 C17 120.63(11) . . ?
C1 C6 C17 121.64(12) . . ?
C8 C7 C1 119.18(12) . . ?
C8 C7 H7 120.4 . . ?
C1 C7 H7 120.4 . . ?
C7 C8 C4 118.87(12) . 3_666 ?
C7 C8 H8 120.6 . . ?
C4 C8 H8 120.6 3_666 . ?
C3 C9 C10 112.35(10) . . ?
C3 C9 H9A 109.1 . . ?
C10 C9 H9A 109.1 . . ?
C3 C9 H9B 109.1 . . ?
C10 C9 H9B 109.1 . . ?
H9A C9 H9B 107.9 . . ?
C11 C10 C9 114.20(10) . . ?
C11 C10 H10A 108.7 . . ?
C9 C10 H10A 108.7 . . ?
C11 C10 H10B 108.7 . . ?
C9 C10 H10B 108.7 . . ?
H10A C10 H10B 107.6 . . ?
C10 C11 C12 113.67(11) . . ?
C10 C11 H11A 108.8 . . ?
C12 C11 H11A 108.8 . . ?
C10 C11 H11B 108.8 . . ?
C12 C11 H11B 108.8 . . ?
H11A C11 H11B 107.7 . . ?
C11 C12 C13 115.03(11) . . ?
C11 C12 H12A 108.5 . . ?
C13 C12 H12A 108.5 . . ?
C11 C12 H12B 108.5 . . ?
C13 C12 H12B 108.5 . . ?
H12A C12 H12B 107.5 . . ?
C14 C13 C12 114.87(12) . . ?
C14 C13 H13A 108.5 . . ?
C12 C13 H13A 108.5 . . ?
C14 C13 H13B 108.5 . . ?
C12 C13 H13B 108.5 . . ?
H13A C13 H13B 107.5 . . ?
C15 C14 C13 114.49(12) . . ?
C15 C14 H14A 108.6 . . ?
C13 C14 H14A 108.6 . . ?
C15 C14 H14B 108.6 . . ?
C13 C14 H14B 108.6 . . ?
H14A C14 H14B 107.6 . . ?
C14 C15 C16 114.53(14) . . ?
C14 C15 H15A 108.6 . . ?
C16 C15 H15A 108.6 . . ?
C14 C15 H15B 108.6 . . ?
C16 C15 H15B 108.6 . . ?
H15A C15 H15B 107.6 . . ?
C15 C16 H16A 109.5 . . ?
C15 C16 H16B 109.5 . . ?
H16A C16 H16B 109.5 . . ?
C15 C16 H16C 109.5 . . ?
H16A C16 H16C 109.5 . . ?
H16B C16 H16C 109.5 . . ?
C6 C17 C18 113.55(10) . . ?
C6 C17 H17A 108.9 . . ?
C18 C17 H17A 108.9 . . ?
C6 C17 H17B 108.9 . . ?
C18 C17 H17B 108.9 . . ?
H17A C17 H17B 107.7 . . ?
C19 C18 C17 112.59(10) . . ?
C19 C18 H18A 109.1 . . ?
C17 C18 H18A 109.1 . . ?
C19 C18 H18B 109.1 . . ?
C17 C18 H18B 109.1 . . ?
H18A C18 H18B 107.8 . . ?
C18 C19 C20 113.47(10) . . ?
C18 C19 H19A 108.9 . . ?
C20 C19 H19A 108.9 . . ?
C18 C19 H19B 108.9 . . ?
C20 C19 H19B 108.9 . . ?
H19A C19 H19B 107.7 . . ?
C21 C20 C19 115.19(11) . . ?
C21 C20 H20A 108.5 . . ?
C19 C20 H20A 108.5 . . ?
C21 C20 H20B 108.5 . . ?
C19 C20 H20B 108.5 . . ?
H20A C20 H20B 107.5 . . ?
C22 C21 C20 115.04(12) . . ?
C22 C21 H21A 108.5 . . ?
C20 C21 H21A 108.5 . . ?
C22 C21 H21B 108.5 . . ?
C20 C21 H21B 108.5 . . ?
H21A C21 H21B 107.5 . . ?
C21 C22 C23 114.63(12) . . ?
C21 C22 H22A 108.6 . . ?
C23 C22 H22A 108.6 . . ?
C21 C22 H22B 108.6 . . ?
C23 C22 H22B 108.6 . . ?
H22A C22 H22B 107.6 . . ?
C24 C23 C22 114.19(14) . . ?
C24 C23 H23A 108.7 . . ?
C22 C23 H23A 108.7 . . ?
C24 C23 H23B 108.7 . . ?
C22 C23 H23B 108.7 . . ?
H23A C23 H23B 107.6 . . ?
C23 C24 H24A 109.5 . . ?
C23 C24 H24B 109.5 . . ?
H24A C24 H24B 109.5 . . ?
C23 C24 H24C 109.5 . . ?
H24A C24 H24C 109.5 . . ?
H24B C24 H24C 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
C6 C1 C2 C3 15.72(17) . . . . ?
C7 C1 C2 C3 -148.55(12) . . . . ?
C1 C2 C3 C4 3.51(18) . . . . ?
C1 C2 C3 C9 179.94(10) . . . . ?
C2 C3 C4 C5 -19.01(17) . . . . ?
C9 C3 C4 C5 164.59(10) . . . . ?
C2 C3 C4 C8 143.84(12) . . . 3_666 ?
C9 C3 C4 C8 -32.56(17) . . . 3_666 ?
C3 C4 C5 C6 16.21(18) . . . . ?
C8 C4 C5 C6 -147.12(12) 3_666 . . . ?
C4 C5 C6 C1 3.06(18) . . . . ?
C4 C5 C6 C17 176.69(11) . . . . ?
C2 C1 C6 C5 -18.57(16) . . . . ?
C7 C1 C6 C5 145.87(12) . . . . ?
C2 C1 C6 C17 167.87(10) . . . . ?
C7 C1 C6 C17 -27.69(17) . . . . ?
C2 C1 C7 C8 86.01(15) . . . . ?
C6 C1 C7 C8 -77.85(15) . . . . ?
C1 C7 C8 C4 -3.04(17) . . . 3_666 ?
C2 C3 C9 C10 88.44(15) . . . . ?
C4 C3 C9 C10 -95.29(15) . . . . ?
C3 C9 C10 C11 176.15(11) . . . . ?
C9 C10 C11 C12 179.88(11) . . . . ?
C10 C11 C12 C13 176.72(11) . . . . ?
C11 C12 C13 C14 -70.91(17) . . . . ?
C12 C13 C14 C15 -175.33(12) . . . . ?
C13 C14 C15 C16 177.67(15) . . . . ?
C5 C6 C17 C18 117.65(13) . . . . ?
C1 C6 C17 C18 -68.99(15) . . . . ?
C6 C17 C18 C19 -172.93(10) . . . . ?
C17 C18 C19 C20 -173.14(11) . . . . ?
C18 C19 C20 C21 -167.36(11) . . . . ?
C19 C20 C21 C22 -57.33(17) . . . . ?
C20 C21 C22 C23 -173.27(13) . . . . ?
C21 C22 C23 C24 -177.71(15) . . . . ?

_diffrn_measured_fraction_theta_max 0.998
_diffrn_reflns_theta_full        25.03
_diffrn_measured_fraction_theta_full 0.998
_refine_diff_density_max         0.231
_refine_diff_density_min         -0.161
_refine_diff_density_rms         0.037

