# 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_seh_bac_a
_database_code_depnum_ccdc_archive 'CCDC 1031859'
_audit_update_record             
;
2014-10-31 deposited with the CCDC.
2015-03-31 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/6
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C46 H46 N2 S2'
_chemical_formula_weight         690.97

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0040 0.0020
'XDISP Program in WinGX L.Kissel & R.H.Pratt Acta Cryst A46 170 1990'
H H 0.0000 0.0000
'XDISP Program in WinGX L.Kissel & R.H.Pratt Acta Cryst A46 170 1990'
N N 0.0076 0.0040
'XDISP Program in WinGX L.Kissel & R.H.Pratt Acta Cryst A46 170 1990'
S S 0.1431 0.1480
'XDISP Program in WinGX L.Kissel & R.H.Pratt Acta Cryst A46 170 1990'

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 21/c'
_space_group_name_Hall           '-P 2ybc'

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

_cell_length_a                   23.6399(19)
_cell_length_b                   5.2070(3)
_cell_length_c                   15.0420(10)
_cell_angle_alpha                90
_cell_angle_beta                 107.545(5)
_cell_angle_gamma                90
_cell_volume                     1765.4(2)
_cell_formula_units_Z            2
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    5749
_cell_measurement_theta_min      2.85
_cell_measurement_theta_max      29.87

_exptl_crystal_description       plate
_exptl_crystal_colour            yellow
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.300
_exptl_crystal_F_000             736
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.150
_exptl_crystal_size_mid          0.110
_exptl_crystal_size_min          0.005
_exptl_absorpt_coefficient_mu    0.233
_shelx_estimated_absorpt_T_min   0.966
_shelx_estimated_absorpt_T_max   0.999
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.774
_exptl_absorpt_correction_T_max  0.999
_exptl_absorpt_process_details   'SADABS 2014/3 Bruker AXS Madison WI USA'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.7749
_diffrn_radiation_type           synchrotron
_diffrn_source                   'Advanced Light Source station 11.3.1'
_diffrn_measurement_device_type  'Bruker D8 with PHOTON 100 detector'
_diffrn_measurement_method       'ω/θ shutterless scans'
_diffrn_detector_area_resol_mean 10.42
_diffrn_reflns_number            16462
_diffrn_reflns_av_unetI/netI     0.0398
_diffrn_reflns_av_R_equivalents  0.0592
_diffrn_reflns_limit_h_min       -25
_diffrn_reflns_limit_h_max       25
_diffrn_reflns_limit_k_min       -5
_diffrn_reflns_limit_k_max       5
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_theta_min         2.953
_diffrn_reflns_theta_max         25.011
_diffrn_reflns_theta_full        25.011
_diffrn_measured_fraction_theta_max 0.991
_diffrn_measured_fraction_theta_full 0.991
_diffrn_reflns_Laue_measured_fraction_max 0.991
_diffrn_reflns_Laue_measured_fraction_full 0.991
_diffrn_reflns_point_group_measured_fraction_max 0.991
_diffrn_reflns_point_group_measured_fraction_full 0.991
_reflns_number_total             2388
_reflns_number_gt                1666
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_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 APEX 2'
_computing_cell_refinement       'Bruker SAINT v8.34a'
_computing_data_reduction        'Bruker SAINT v8.34a'
_computing_structure_solution    'Bruker SHELXTL 2014/3 beta'
_computing_structure_refinement  'SHELXL-2014/6 (Sheldrick, 2014)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL & local programs'
_refine_special_details          
; 
 The data were cut to 0.92 Angstroms as at that point I/sigma(I) <2
 and therefore the data above this was unobserved. The crystal was
 a very thin plate which explains the displacement parameters all
 pointing in the same direction. All non-hydrogen atoms were refined
 anisotropically. Hydrogen atoms were placed geometrically and
 constrained and refined using a riding model. Displacement parameter
 restrains were used in modelling the disorder in the alkyl chain.
;
_vrf_THETM01_seh_bac_a           
;
PROBLEM: The value of sine(theta_max)/wavelength is less than 0.550
RESPONSE: The data were cut to 0.92 Angstroms as at that point
 I/sigma(I) <2 and therefore the data above this was unobserved.
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0520P)²+3.6058P] 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       0.0061(14)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         2388
_refine_ls_number_parameters     247
_refine_ls_number_restraints     38
_refine_ls_R_factor_all          0.0986
_refine_ls_R_factor_gt           0.0661
_refine_ls_wR_factor_ref         0.1749
_refine_ls_wR_factor_gt          0.1554
_refine_ls_goodness_of_fit_ref   1.084
_refine_ls_restrained_S_all      1.102
_refine_ls_shift/su_max          0.000
_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
S1 S 0.73630(7) 0.1925(2) 0.64656(9) 0.0672(5) Uani 1 1 d . . . . .
N1 N 0.6400(2) 0.3561(6) 0.5267(3) 0.0532(11) Uani 1 1 d . . . . .
C1 C 0.6591(2) 0.1879(8) 0.5939(3) 0.0535(13) Uani 1 1 d . . . . .
C2 C 0.6195(3) 0.0057(7) 0.6196(3) 0.0495(13) Uani 1 1 d . . . . .
C3 C 0.5610(2) -0.0002(7) 0.5614(3) 0.0477(13) Uani 1 1 d . . . . .
C4 C 0.5415(2) 0.1774(7) 0.4868(3) 0.0469(13) Uani 1 1 d . . . . .
C5 C 0.4823(2) 0.1818(7) 0.4264(3) 0.0475(13) Uani 1 1 d . . . . .
C6 C 0.4642(2) 0.3671(7) 0.3554(3) 0.0487(13) Uani 1 1 d . . . . .
C7 C 0.5072(3) 0.5492(8) 0.3462(3) 0.0511(14) Uani 1 1 d . . . . .
H7A H 0.4958 0.6768 0.2990 0.061 Uiso 1 1 calc R U . . .
C8 C 0.5635(3) 0.5449(8) 0.4025(3) 0.0526(14) Uani 1 1 d . . . . .
H8A H 0.5909 0.6690 0.3943 0.063 Uiso 1 1 calc R U . . .
C9 C 0.5826(3) 0.3582(7) 0.4742(3) 0.0483(13) Uani 1 1 d . . . . .
C10 C 0.4048(3) 0.3634(7) 0.2934(3) 0.0511(14) Uani 1 1 d . . . . .
C11 C 0.3857(3) 0.5424(8) 0.2196(3) 0.0569(14) Uani 1 1 d . . . . .
H11A H 0.4120 0.6762 0.2149 0.068 Uiso 1 1 calc R U . . .
C12 C 0.3313(3) 0.5308(9) 0.1553(4) 0.0618(15) Uani 1 1 d . . . . .
H12A H 0.3200 0.6576 0.1078 0.074 Uiso 1 1 calc R U . . .
C13 C 0.2919(3) 0.3342(9) 0.1584(3) 0.0633(14) Uani 1 1 d . . . . .
H13A H 0.2546 0.3205 0.1119 0.076 Uiso 1 1 calc R U . . .
C14 C 0.3085(3) 0.1600(9) 0.2307(3) 0.0595(14) Uani 1 1 d . . . . .
H14A H 0.2817 0.0261 0.2330 0.071 Uiso 1 1 calc R U . . .
C15 C 0.3631(2) 0.1713(8) 0.3012(3) 0.0523(13) Uani 1 1 d . . . . .
C16 C 0.7586(3) 0.4529(11) 0.5847(3) 0.0767(17) Uani 1 1 d . . . . .
H16C H 0.7431 0.4226 0.5166 0.092 Uiso 0.4 1 calc R U P A 2
H16D H 0.7419 0.6168 0.5988 0.092 Uiso 0.4 1 calc R U P A 2
H16A H 0.7431 0.4226 0.5166 0.092 Uiso 0.6 1 calc R U P B 1
H16B H 0.7419 0.6168 0.5988 0.092 Uiso 0.6 1 calc R U P B 1
C17 C 0.8257(3) 0.4693(15) 0.6141(4) 0.097(2) Uani 1 1 d . . . . .
H17B H 0.8295 0.6328 0.5815 0.116 Uiso 0.4 1 calc R U P C 2
H17A H 0.8368 0.2835 0.6207 0.116 Uiso 0.6 1 calc R U P D 1
C18 C 0.8508(3) 0.5607(13) 0.7120(4) 0.095(2) Uani 1 1 d . U . . .
H18A H 0.8334 0.7320 0.7152 0.114 Uiso 1 1 calc R U . . .
H18B H 0.8353 0.4448 0.7514 0.114 Uiso 1 1 calc R U . . .
C19 C 0.9124(4) 0.584(2) 0.7561(5) 0.156(3) Uani 1 1 d . U . . .
H19A H 0.9296 0.4152 0.7477 0.187 Uiso 1 1 calc R U . . .
H19B H 0.9268 0.7076 0.7180 0.187 Uiso 1 1 calc R U . . .
C20 C 0.9400(4) 0.653(2) 0.8491(5) 0.148(3) Uani 1 1 d D U . . .
H20C H 0.9173 0.5729 0.8874 0.177 Uiso 0.4 1 calc R U P E 2
H20D H 0.9356 0.8415 0.8537 0.177 Uiso 0.4 1 calc R U P E 2
H20A H 0.9494 0.4877 0.8826 0.177 Uiso 0.6 1 calc R U P F 1
H20B H 0.9078 0.7303 0.8698 0.177 Uiso 0.6 1 calc R U P F 1
C21 C 0.9909(11) 0.813(6) 0.891(2) 0.196(12) Uani 0.4 1 d D U P G 1
H21A H 0.9978 0.8197 0.9587 0.294 Uiso 0.4 1 calc R U P G 1
H21B H 1.0258 0.7403 0.8782 0.294 Uiso 0.4 1 calc R U P G 1
H21C H 0.9836 0.9865 0.8652 0.294 Uiso 0.4 1 calc R U P G 1
C21' C 1.0024(6) 0.591(4) 0.8922(13) 0.170(8) Uani 0.6 1 d D U P G 2
H21D H 1.0150 0.6525 0.9568 0.256 Uiso 0.6 1 calc R U P G 2
H21E H 1.0079 0.4050 0.8913 0.256 Uiso 0.6 1 calc R U P G 2
H21F H 1.0263 0.6752 0.8574 0.256 Uiso 0.6 1 calc R U P G 2
C22 C 0.8519(5) 0.553(2) 0.5373(6) 0.085(3) Uani 0.6 1 d . . P H 1
H22A H 0.8956 0.5677 0.5639 0.102 Uiso 0.6 1 calc R U P H 1
H22B H 0.8363 0.7251 0.5144 0.102 Uiso 0.6 1 calc R U P H 1
C22' C 0.8483(7) 0.321(3) 0.5694(11) 0.084(5) Uani 0.4 1 d . . P H 2
H22C H 0.8343 0.1459 0.5773 0.101 Uiso 0.4 1 calc R U P H 2
H22D H 0.8917 0.3232 0.6002 0.101 Uiso 0.4 1 calc R U P H 2
C23 C 0.8375(3) 0.3646(16) 0.4544(5) 0.124(3) Uani 1 1 d . . . . .
H23D H 0.8585 0.2305 0.4313 0.187 Uiso 0.4 1 calc R U P H 2
H23E H 0.7950 0.3549 0.4210 0.187 Uiso 0.4 1 calc R U P H 2
H23F H 0.8527 0.5334 0.4441 0.187 Uiso 0.4 1 calc R U P H 2
H23A H 0.8553 0.4269 0.4074 0.187 Uiso 0.6 1 calc R U P H 1
H23B H 0.8536 0.1948 0.4763 0.187 Uiso 0.6 1 calc R U P H 1
H23C H 0.7944 0.3522 0.4268 0.187 Uiso 0.6 1 calc R U P H 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_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
S1 C1 1.758(5) . ?
S1 C16 1.810(5) . ?
N1 C1 1.310(5) . ?
N1 C9 1.348(6) . ?
C1 C2 1.464(6) . ?
C2 C3 1.396(6) . ?
C2 C15 1.463(6) 3_656 ?
C3 C4 1.420(6) . ?
C3 C5 1.445(6) 3_656 ?
C4 C9 1.406(6) . ?
C4 C5 1.420(6) . ?
C5 C6 1.407(6) . ?
C5 C3 1.445(6) 3_656 ?
C6 C7 1.427(6) . ?
C6 C10 1.433(7) . ?
C7 C8 1.345(6) . ?
C7 H7A 0.9500 . ?
C8 C9 1.420(6) . ?
C8 H8A 0.9500 . ?
C10 C11 1.415(6) . ?
C10 C15 1.434(6) . ?
C11 C12 1.358(7) . ?
C11 H11A 0.9500 . ?
C12 C13 1.394(7) . ?
C12 H12A 0.9500 . ?
C13 C14 1.379(6) . ?
C13 H13A 0.9500 . ?
C14 C15 1.403(7) . ?
C14 H14A 0.9500 . ?
C15 C2 1.464(6) 3_656 ?
C16 C17 1.515(8) . ?
C16 H16C 0.9900 . ?
C16 H16D 0.9900 . ?
C16 H16A 0.9900 . ?
C16 H16B 0.9900 . ?
C17 C22' 1.244(13) . ?
C17 C18 1.490(8) . ?
C17 C22 1.531(10) . ?
C17 H17B 1.0000 . ?
C17 H17A 1.0000 . ?
C18 C19 1.410(9) . ?
C18 H18A 0.9900 . ?
C18 H18B 0.9900 . ?
C19 C20 1.402(9) . ?
C19 H19A 0.9900 . ?
C19 H19B 0.9900 . ?
C20 C21 1.441(13) . ?
C20 C21' 1.457(12) . ?
C20 H20C 0.9900 . ?
C20 H20D 0.9900 . ?
C20 H20A 0.9900 . ?
C20 H20B 0.9900 . ?
C21 H21A 0.9800 . ?
C21 H21B 0.9800 . ?
C21 H21C 0.9800 . ?
C21' H21D 0.9800 . ?
C21' H21E 0.9800 . ?
C21' H21F 0.9800 . ?
C22 C23 1.542(11) . ?
C22 H22A 0.9900 . ?
C22 H22B 0.9900 . ?
C22' C23 1.686(15) . ?
C22' H22C 0.9900 . ?
C22' H22D 0.9900 . ?
C23 H23D 0.9800 . ?
C23 H23E 0.9800 . ?
C23 H23F 0.9800 . ?
C23 H23A 0.9800 . ?
C23 H23B 0.9800 . ?
C23 H23C 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
C1 S1 C16 101.6(2) . . ?
C1 N1 C9 120.6(4) . . ?
N1 C1 C2 122.6(5) . . ?
N1 C1 S1 114.1(4) . . ?
C2 C1 S1 123.3(4) . . ?
C3 C2 C15 118.6(4) . 3_656 ?
C3 C2 C1 116.0(4) . . ?
C15 C2 C1 125.3(5) 3_656 . ?
C2 C3 C4 120.4(4) . . ?
C2 C3 C5 122.7(4) . 3_656 ?
C4 C3 C5 116.9(5) . 3_656 ?
C9 C4 C3 118.0(5) . . ?
C9 C4 C5 119.4(4) . . ?
C3 C4 C5 122.6(4) . . ?
C6 C5 C4 120.7(4) . . ?
C6 C5 C3 118.7(5) . 3_656 ?
C4 C5 C3 120.5(4) . 3_656 ?
C5 C6 C7 117.9(5) . . ?
C5 C6 C10 119.9(4) . . ?
C7 C6 C10 122.2(4) . . ?
C8 C7 C6 121.7(4) . . ?
C8 C7 H7A 119.1 . . ?
C6 C7 H7A 119.1 . . ?
C7 C8 C9 121.2(5) . . ?
C7 C8 H8A 119.4 . . ?
C9 C8 H8A 119.4 . . ?
N1 C9 C4 122.0(4) . . ?
N1 C9 C8 119.0(4) . . ?
C4 C9 C8 119.0(5) . . ?
C11 C10 C6 121.4(4) . . ?
C11 C10 C15 117.3(5) . . ?
C6 C10 C15 121.3(4) . . ?
C12 C11 C10 122.6(5) . . ?
C12 C11 H11A 118.7 . . ?
C10 C11 H11A 118.7 . . ?
C11 C12 C13 120.5(5) . . ?
C11 C12 H12A 119.8 . . ?
C13 C12 H12A 119.8 . . ?
C14 C13 C12 118.4(5) . . ?
C14 C13 H13A 120.8 . . ?
C12 C13 H13A 120.8 . . ?
C13 C14 C15 123.1(5) . . ?
C13 C14 H14A 118.5 . . ?
C15 C14 H14A 118.5 . . ?
C14 C15 C10 117.8(4) . . ?
C14 C15 C2 123.8(4) . 3_656 ?
C10 C15 C2 118.3(5) . 3_656 ?
C17 C16 S1 109.5(4) . . ?
C17 C16 H16C 109.8 . . ?
S1 C16 H16C 109.8 . . ?
C17 C16 H16D 109.8 . . ?
S1 C16 H16D 109.8 . . ?
H16C C16 H16D 108.2 . . ?
C17 C16 H16A 109.8 . . ?
S1 C16 H16A 109.8 . . ?
C17 C16 H16B 109.8 . . ?
S1 C16 H16B 109.8 . . ?
H16A C16 H16B 108.2 . . ?
C22' C17 C18 128.6(11) . . ?
C22' C17 C16 112.9(9) . . ?
C18 C17 C16 112.2(5) . . ?
C18 C17 C22 121.6(6) . . ?
C16 C17 C22 115.0(6) . . ?
C22' C17 H17B 98.4 . . ?
C18 C17 H17B 98.4 . . ?
C16 C17 H17B 98.4 . . ?
C18 C17 H17A 101.3 . . ?
C16 C17 H17A 101.3 . . ?
C22 C17 H17A 101.3 . . ?
C19 C18 C17 122.6(6) . . ?
C19 C18 H18A 106.7 . . ?
C17 C18 H18A 106.7 . . ?
C19 C18 H18B 106.7 . . ?
C17 C18 H18B 106.7 . . ?
H18A C18 H18B 106.6 . . ?
C20 C19 C18 126.5(8) . . ?
C20 C19 H19A 105.7 . . ?
C18 C19 H19A 105.7 . . ?
C20 C19 H19B 105.7 . . ?
C18 C19 H19B 105.7 . . ?
H19A C19 H19B 106.1 . . ?
C19 C20 C21 131.6(17) . . ?
C19 C20 C21' 119.4(12) . . ?
C19 C20 H20C 107.5 . . ?
C21' C20 H20C 107.5 . . ?
C19 C20 H20D 107.5 . . ?
C21' C20 H20D 107.5 . . ?
H20C C20 H20D 107.0 . . ?
C19 C20 H20A 104.4 . . ?
C21 C20 H20A 104.4 . . ?
C19 C20 H20B 104.4 . . ?
C21 C20 H20B 104.4 . . ?
H20A C20 H20B 105.6 . . ?
C20 C21 H21A 109.5 . . ?
C20 C21 H21B 109.5 . . ?
H21A C21 H21B 109.5 . . ?
C20 C21 H21C 109.5 . . ?
H21A C21 H21C 109.5 . . ?
H21B C21 H21C 109.5 . . ?
C20 C21' H21D 109.5 . . ?
C20 C21' H21E 109.5 . . ?
H21D C21' H21E 109.5 . . ?
C20 C21' H21F 109.5 . . ?
H21D C21' H21F 109.5 . . ?
H21E C21' H21F 109.5 . . ?
C17 C22 C23 112.8(8) . . ?
C17 C22 H22A 109.0 . . ?
C23 C22 H22A 109.0 . . ?
C17 C22 H22B 109.0 . . ?
C23 C22 H22B 109.0 . . ?
H22A C22 H22B 107.8 . . ?
C17 C22' C23 121.0(12) . . ?
C17 C22' H22C 107.1 . . ?
C23 C22' H22C 107.1 . . ?
C17 C22' H22D 107.1 . . ?
C23 C22' H22D 107.1 . . ?
H22C C22' H22D 106.8 . . ?
C22' C23 H23D 109.5 . . ?
C22' C23 H23E 109.5 . . ?
H23D C23 H23E 109.5 . . ?
C22' C23 H23F 109.5 . . ?
H23D C23 H23F 109.5 . . ?
H23E C23 H23F 109.5 . . ?
C22 C23 H23A 109.5 . . ?
C22 C23 H23B 109.5 . . ?
H23A C23 H23B 109.5 . . ?
C22 C23 H23C 109.5 . . ?
H23A C23 H23C 109.5 . . ?
H23B C23 H23C 109.5 . . ?

_refine_diff_density_max         0.256
_refine_diff_density_min         -0.260
_refine_diff_density_rms         0.050

_shelxl_version_number           2014/6



####################################################################### 
# 
# 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_seh_tac_a
_database_code_depnum_ccdc_archive 'CCDC 1031861'
_audit_update_record             
;
2014-10-31 deposited with the CCDC.
2015-03-31 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/6
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C42 H42 N2 S4'
_chemical_formula_weight         703.01

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0040 0.0020
'XDISP Program in WinGX L.Kissel & R.H.Pratt Acta Cryst A46 170 1990'
H H 0.0000 0.0000
'XDISP Program in WinGX L.Kissel & R.H.Pratt Acta Cryst A46 170 1990'
N N 0.0076 0.0040
'XDISP Program in WinGX L.Kissel & R.H.Pratt Acta Cryst A46 170 1990'
S S 0.1431 0.1480
'XDISP Program in WinGX L.Kissel & R.H.Pratt Acta Cryst A46 170 1990'

_space_group_crystal_system      trigonal
_space_group_IT_number           148
_space_group_name_H-M_alt        'R -3 :H'
_space_group_name_Hall           '-R 3'

_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'
'-y, x-y, z'
'-x+y, -x, z'
'x+2/3, y+1/3, z+1/3'
'-y+2/3, x-y+1/3, z+1/3'
'-x+y+2/3, -x+1/3, z+1/3'
'x+1/3, y+2/3, z+2/3'
'-y+1/3, x-y+2/3, z+2/3'
'-x+y+1/3, -x+2/3, z+2/3'
'-x, -y, -z'
'y, -x+y, -z'
'x-y, x, -z'
'-x+2/3, -y+1/3, -z+1/3'
'y+2/3, -x+y+1/3, -z+1/3'
'x-y+2/3, x+1/3, -z+1/3'
'-x+1/3, -y+2/3, -z+2/3'
'y+1/3, -x+y+2/3, -z+2/3'
'x-y+1/3, x+2/3, -z+2/3'

_cell_length_a                   43.2109(16)
_cell_length_b                   43.2109(16)
_cell_length_c                   5.0578(2)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                120
_cell_volume                     8178.6(7)
_cell_formula_units_Z            9
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    9986
_cell_measurement_theta_min      2.72
_cell_measurement_theta_max      33.69

_exptl_crystal_description       needle
_exptl_crystal_colour            yellow
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.285
_exptl_crystal_F_000             3348
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.300
_exptl_crystal_size_mid          0.050
_exptl_crystal_size_min          0.040
_exptl_absorpt_coefficient_mu    0.368
_shelx_estimated_absorpt_T_min   0.898
_shelx_estimated_absorpt_T_max   0.985
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.888
_exptl_absorpt_correction_T_max  0.985
_exptl_absorpt_process_details   'SADABS 2014/3 Bruker AXS Madison WI USA'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.7749
_diffrn_radiation_type           synchrotron
_diffrn_source                   'Advanced Light Source station 11.3.1'
_diffrn_measurement_device_type  'Bruker D8 with PHOTON 100 detector'
_diffrn_measurement_method       'ω/θ shutterless scans'
_diffrn_detector_area_resol_mean 10.42
_diffrn_reflns_number            46645
_diffrn_reflns_av_unetI/netI     0.0310
_diffrn_reflns_av_R_equivalents  0.0475
_diffrn_reflns_limit_h_min       -61
_diffrn_reflns_limit_h_max       61
_diffrn_reflns_limit_k_min       -61
_diffrn_reflns_limit_k_max       61
_diffrn_reflns_limit_l_min       -7
_diffrn_reflns_limit_l_max       7
_diffrn_reflns_theta_min         2.719
_diffrn_reflns_theta_max         33.641
_diffrn_reflns_theta_full        27.706
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measured_fraction_theta_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_point_group_measured_fraction_full 0.998
_reflns_number_total             5560
_reflns_number_gt                4614
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_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 APEX 2'
_computing_cell_refinement       'Bruker SAINT v8.34a'
_computing_data_reduction        'Bruker SAINT v8.34a'
_computing_structure_solution    'Bruker SHELXTL 2014/3 beta'
_computing_structure_refinement  'SHELXL-2014/6 (Sheldrick, 2014)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL & local programs'
_refine_special_details          
; 
 All non-hydrogen atoms were refined anisotropically, except for
 the 20% occupied alkyl chain. Hydrogen atoms were placed
 geometrically and constrained. All hydrogen atoms were refined
 using a riding model. Displacement parameter restrains were used
 in modelling the disorder in the alkyl chain.
;
_vrf_PLAT222_seh_tac_a           
;
PROBLEM: Large Non-Solvent    H    Uiso(max)/Uiso(min) ..       10.0 Ratio 
RESPONSE: The carbon atoms at the end of the alkyl chain shows disorder
 in the form of a larger than ideal displacement parameter, the hydrogen
 is attached to this. 
;
_vrf_PLAT220_seh_tac_a           
;
PROBLEM: Large Non-Solvent  C     Ueq(max)/Ueq(min) Range       10.0 Ratio 
RESPONSE: The carbon atoms at the end of the alkyl chain shows disorder
 in the form of a larger than ideal displacement parameter.
;
_vrf_PLAT601_seh_tac_a           
;
PROBLEM: Structure Contains Solvent Accessible VOIDS of .        127 Ang3  
RESPONSE: Less than 0.5 electrons per cubic angstrom were observed in this
 void, and nothing that looked like a toluene solvent molecule.
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0583P)²+32.4510P] 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         5560
_refine_ls_number_parameters     245
_refine_ls_number_restraints     178
_refine_ls_R_factor_all          0.0707
_refine_ls_R_factor_gt           0.0583
_refine_ls_wR_factor_ref         0.1560
_refine_ls_wR_factor_gt          0.1502
_refine_ls_goodness_of_fit_ref   1.099
_refine_ls_restrained_S_all      1.111
_refine_ls_shift/su_max          0.013
_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_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
S1 S 0.61563(2) 0.61379(2) 1.45286(10) 0.02436(13) Uani 1 1 d . . . . .
N1 N 0.44888(5) 0.51080(5) 0.4518(3) 0.0220(3) Uani 1 1 d . . . . .
C1 C 0.43029(5) 0.47606(6) 0.4878(4) 0.0209(4) Uani 1 1 d . . . . .
S2 S 0.39182(2) 0.45209(2) 0.29103(11) 0.02644(14) Uani 1 1 d . . . . .
C2 C 0.43917(5) 0.45694(5) 0.6783(4) 0.0194(4) Uani 1 1 d . . . . .
C3 C 0.46927(5) 0.47782(5) 0.8390(4) 0.0183(4) Uani 1 1 d . . . . .
C4 C 0.48910(5) 0.51554(5) 0.8037(4) 0.0187(4) Uani 1 1 d . . . . .
C5 C 0.51952(5) 0.53784(5) 0.9617(4) 0.0187(4) Uani 1 1 d . . . . .
C6 C 0.53848(5) 0.57507(5) 0.9196(4) 0.0207(4) Uani 1 1 d . . . . .
C7 C 0.52671(6) 0.58960(6) 0.7168(4) 0.0235(4) Uani 1 1 d . . . . .
H7A H 0.5393 0.6147 0.6864 0.028 Uiso 1 1 calc R U . . .
C8 C 0.49763(6) 0.56821(6) 0.5651(4) 0.0231(4) Uani 1 1 d . . . . .
H8A H 0.4904 0.5785 0.4302 0.028 Uiso 1 1 calc R U . . .
C9 C 0.47814(5) 0.53086(5) 0.6062(4) 0.0203(4) Uani 1 1 d . . . . .
C10 C 0.61599(6) 0.64718(6) 1.2652(4) 0.0269(4) Uani 1 1 d . . . . .
H10A H 0.6326 0.6719 1.2902 0.032 Uiso 1 1 calc R U . . .
C11 C 0.59025(6) 0.63462(6) 1.0789(4) 0.0248(4) Uani 1 1 d . . . . .
H11A H 0.5869 0.6495 0.9575 0.030 Uiso 1 1 calc R U . . .
C12 C 0.56849(6) 0.59649(5) 1.0835(4) 0.0213(4) Uani 1 1 d . . . . .
C13 C 0.57932(5) 0.58090(5) 1.2795(4) 0.0209(4) Uani 1 1 d . . . . .
C14 C 0.39297(7) 0.48677(7) 0.0847(5) 0.0310(5) Uani 1 1 d D U . . .
H14C H 0.4179 0.5069 0.0814 0.037 Uiso 0.2 1 calc R U P A 2
H14D H 0.3869 0.4773 -0.0977 0.037 Uiso 0.2 1 calc R U P A 2
H14A H 0.4177 0.5022 0.0212 0.037 Uiso 0.8 1 calc R U P B 1
H14B H 0.3777 0.4755 -0.0721 0.037 Uiso 0.8 1 calc R U P B 1
C15 C 0.38035(9) 0.51058(9) 0.2226(7) 0.0349(7) Uani 0.8 1 d D U P C 1
H15A H 0.3968 0.5228 0.3746 0.042 Uiso 0.8 1 calc R U P C 1
C16 C 0.38434(11) 0.53922(10) 0.0284(9) 0.0512(9) Uani 0.8 1 d D U P C 1
H16A H 0.3731 0.5276 -0.1412 0.061 Uiso 0.8 1 calc R U P C 1
H16B H 0.3712 0.5508 0.0981 0.061 Uiso 0.8 1 calc R U P C 1
C17 C 0.42105(14) 0.56648(14) -0.0216(12) 0.0698(13) Uani 0.8 1 d D U P C 1
H17A H 0.4340 0.5549 -0.0948 0.084 Uiso 0.8 1 calc R U P C 1
H17B H 0.4325 0.5777 0.1487 0.084 Uiso 0.8 1 calc R U P C 1
C18 C 0.4253(2) 0.59639(18) -0.2161(15) 0.105(2) Uani 0.8 1 d D U P C 1
H18A H 0.4510 0.6123 -0.2541 0.126 Uiso 0.8 1 calc R U P C 1
H18B H 0.4133 0.5853 -0.3847 0.126 Uiso 0.8 1 calc R U P C 1
C19 C 0.4108(3) 0.6173(3) -0.115(3) 0.192(5) Uani 0.8 1 d D U P C 1
H19A H 0.4143 0.6356 -0.2451 0.288 Uiso 0.8 1 calc R U P C 1
H19B H 0.3853 0.6018 -0.0809 0.288 Uiso 0.8 1 calc R U P C 1
H19C H 0.4230 0.6288 0.0497 0.288 Uiso 0.8 1 calc R U P C 1
C20 C 0.34219(9) 0.48899(10) 0.3329(7) 0.0376(7) Uani 0.8 1 d D U P C 1
H20A H 0.3417 0.4719 0.4660 0.045 Uiso 0.8 1 calc R U P C 1
H20B H 0.3364 0.5056 0.4253 0.045 Uiso 0.8 1 calc R U P C 1
C21 C 0.31339(10) 0.46830(11) 0.1297(8) 0.0441(8) Uani 0.8 1 d D U P C 1
H21A H 0.2901 0.4555 0.2179 0.066 Uiso 0.8 1 calc R U P C 1
H21B H 0.3130 0.4849 -0.0005 0.066 Uiso 0.8 1 calc R U P C 1
H21C H 0.3184 0.4512 0.0402 0.066 Uiso 0.8 1 calc R U P C 1
C15' C 0.3687(4) 0.5021(4) 0.157(4) 0.047(3) Uiso 0.2 1 d D U P C 2
H15' H 0.3680 0.5146 -0.0073 0.057 Uiso 0.2 1 calc R U P C 2
C16' C 0.3881(6) 0.5320(5) 0.354(4) 0.082(4) Uiso 0.2 1 d D U P C 2
H16C H 0.3786 0.5211 0.5290 0.099 Uiso 0.2 1 calc R U P C 2
H16D H 0.4132 0.5373 0.3501 0.099 Uiso 0.2 1 calc R U P C 2
C17' C 0.3904(9) 0.5671(6) 0.362(5) 0.113(7) Uiso 0.2 1 d D U P C 2
H17C H 0.4140 0.5855 0.4298 0.135 Uiso 0.2 1 calc R U P C 2
H17D H 0.3716 0.5663 0.4793 0.135 Uiso 0.2 1 calc R U P C 2
C18' C 0.3850(8) 0.5756(7) 0.079(5) 0.092(5) Uiso 0.2 1 d D U P C 2
H18C H 0.4044 0.5774 -0.0364 0.110 Uiso 0.2 1 calc R U P C 2
H18D H 0.3618 0.5566 0.0089 0.110 Uiso 0.2 1 calc R U P C 2
C19' C 0.386(2) 0.6095(12) 0.090(12) 0.250(17) Uiso 0.2 1 d D U P C 2
H19D H 0.3823 0.6163 -0.0878 0.375 Uiso 0.2 1 calc R U P C 2
H19E H 0.3664 0.6072 0.2058 0.375 Uiso 0.2 1 calc R U P C 2
H19F H 0.4087 0.6279 0.1607 0.375 Uiso 0.2 1 calc R U P C 2
C20' C 0.3301(4) 0.4745(4) 0.205(4) 0.047(3) Uiso 0.2 1 d D U P C 2
H20C H 0.3221 0.4578 0.0529 0.057 Uiso 0.2 1 calc R U P C 2
H20D H 0.3294 0.4605 0.3625 0.057 Uiso 0.2 1 calc R U P C 2
C21' C 0.3029(6) 0.4857(7) 0.246(5) 0.087(6) Uiso 0.2 1 d D U P C 2
H21D H 0.2794 0.4646 0.2744 0.130 Uiso 0.2 1 calc R U P C 2
H21E H 0.3095 0.5014 0.4014 0.130 Uiso 0.2 1 calc R U P C 2
H21F H 0.3021 0.4987 0.0899 0.130 Uiso 0.2 1 calc R U P C 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
S1 C10 1.721(2) . ?
S1 C13 1.738(2) . ?
N1 C1 1.314(3) . ?
N1 C9 1.366(3) . ?
C1 C2 1.440(3) . ?
C1 S2 1.762(2) . ?
S2 C14 1.806(2) . ?
C2 C3 1.412(3) . ?
C2 C13 1.432(3) 10_667 ?
C3 C4 1.423(3) . ?
C3 C5 1.427(3) 10_667 ?
C4 C9 1.405(3) . ?
C4 C5 1.424(3) . ?
C5 C6 1.409(3) . ?
C5 C3 1.427(3) 10_667 ?
C6 C7 1.423(3) . ?
C6 C12 1.423(3) . ?
C7 C8 1.364(3) . ?
C7 H7A 0.9500 . ?
C8 C9 1.414(3) . ?
C8 H8A 0.9500 . ?
C10 C11 1.347(3) . ?
C10 H10A 0.9500 . ?
C11 C12 1.432(3) . ?
C11 H11A 0.9500 . ?
C12 C13 1.404(3) . ?
C13 C2 1.432(3) 10_667 ?
C14 C15' 1.540(13) . ?
C14 C15 1.550(4) . ?
C14 H14C 0.9900 . ?
C14 H14D 0.9900 . ?
C14 H14A 0.9900 . ?
C14 H14B 0.9900 . ?
C15 C16 1.520(5) . ?
C15 C20 1.537(5) . ?
C15 H15A 1.0000 . ?
C16 C17 1.449(7) . ?
C16 H16A 0.9900 . ?
C16 H16B 0.9900 . ?
C17 C18 1.560(8) . ?
C17 H17A 0.9900 . ?
C17 H17B 0.9900 . ?
C18 C19 1.425(12) . ?
C18 H18A 0.9900 . ?
C18 H18B 0.9900 . ?
C19 H19A 0.9800 . ?
C19 H19B 0.9800 . ?
C19 H19C 0.9800 . ?
C20 C21 1.514(4) . ?
C20 H20A 0.9900 . ?
C20 H20B 0.9900 . ?
C21 H21A 0.9800 . ?
C21 H21B 0.9800 . ?
C21 H21C 0.9800 . ?
C15' C20' 1.508(15) . ?
C15' C16' 1.509(16) . ?
C15' H15' 1.0000 . ?
C16' C17' 1.471(18) . ?
C16' H16C 0.9900 . ?
C16' H16D 0.9900 . ?
C17' C18' 1.525(19) . ?
C17' H17C 0.9900 . ?
C17' H17D 0.9900 . ?
C18' C19' 1.45(2) . ?
C18' H18C 0.9900 . ?
C18' H18D 0.9900 . ?
C19' H19D 0.9800 . ?
C19' H19E 0.9800 . ?
C19' H19F 0.9800 . ?
C20' C21' 1.495(16) . ?
C20' H20C 0.9900 . ?
C20' H20D 0.9900 . ?
C21' H21D 0.9800 . ?
C21' H21E 0.9800 . ?
C21' H21F 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
C10 S1 C13 91.90(10) . . ?
C1 N1 C9 119.27(17) . . ?
N1 C1 C2 124.20(18) . . ?
N1 C1 S2 116.81(15) . . ?
C2 C1 S2 118.98(15) . . ?
C1 S2 C14 102.26(11) . . ?
C3 C2 C13 116.96(18) . 10_667 ?
C3 C2 C1 116.32(18) . . ?
C13 C2 C1 126.72(18) 10_667 . ?
C2 C3 C4 119.61(18) . . ?
C2 C3 C5 121.77(18) . 10_667 ?
C4 C3 C5 118.62(17) . 10_667 ?
C9 C4 C3 118.50(18) . . ?
C9 C4 C5 119.64(18) . . ?
C3 C4 C5 121.86(17) . . ?
C6 C5 C4 120.06(18) . . ?
C6 C5 C3 120.42(18) . 10_667 ?
C4 C5 C3 119.52(17) . 10_667 ?
C5 C6 C7 118.71(19) . . ?
C5 C6 C12 118.37(18) . . ?
C7 C6 C12 122.92(19) . . ?
C8 C7 C6 121.20(19) . . ?
C8 C7 H7A 119.4 . . ?
C6 C7 H7A 119.4 . . ?
C7 C8 C9 120.79(19) . . ?
C7 C8 H8A 119.6 . . ?
C9 C8 H8A 119.6 . . ?
N1 C9 C4 122.06(18) . . ?
N1 C9 C8 118.33(18) . . ?
C4 C9 C8 119.60(19) . . ?
C11 C10 S1 112.86(17) . . ?
C11 C10 H10A 123.6 . . ?
S1 C10 H10A 123.6 . . ?
C10 C11 C12 112.8(2) . . ?
C10 C11 H11A 123.6 . . ?
C12 C11 H11A 123.6 . . ?
C13 C12 C6 120.87(18) . . ?
C13 C12 C11 112.27(19) . . ?
C6 C12 C11 126.84(19) . . ?
C12 C13 C2 121.58(18) . 10_667 ?
C12 C13 S1 110.19(15) . . ?
C2 C13 S1 128.20(16) 10_667 . ?
C15' C14 S2 118.5(7) . . ?
C15 C14 S2 114.7(2) . . ?
C15' C14 H14C 107.7 . . ?
S2 C14 H14C 107.7 . . ?
C15' C14 H14D 107.7 . . ?
S2 C14 H14D 107.7 . . ?
H14C C14 H14D 107.1 . . ?
C15 C14 H14A 108.6 . . ?
S2 C14 H14A 108.6 . . ?
C15 C14 H14B 108.6 . . ?
S2 C14 H14B 108.6 . . ?
H14A C14 H14B 107.6 . . ?
C16 C15 C20 112.3(3) . . ?
C16 C15 C14 108.4(3) . . ?
C20 C15 C14 112.8(3) . . ?
C16 C15 H15A 107.7 . . ?
C20 C15 H15A 107.7 . . ?
C14 C15 H15A 107.7 . . ?
C17 C16 C15 114.0(4) . . ?
C17 C16 H16A 108.7 . . ?
C15 C16 H16A 108.7 . . ?
C17 C16 H16B 108.7 . . ?
C15 C16 H16B 108.7 . . ?
H16A C16 H16B 107.6 . . ?
C16 C17 C18 114.3(5) . . ?
C16 C17 H17A 108.7 . . ?
C18 C17 H17A 108.7 . . ?
C16 C17 H17B 108.7 . . ?
C18 C17 H17B 108.7 . . ?
H17A C17 H17B 107.6 . . ?
C19 C18 C17 113.0(8) . . ?
C19 C18 H18A 109.0 . . ?
C17 C18 H18A 109.0 . . ?
C19 C18 H18B 109.0 . . ?
C17 C18 H18B 109.0 . . ?
H18A C18 H18B 107.8 . . ?
C18 C19 H19A 109.5 . . ?
C18 C19 H19B 109.5 . . ?
H19A C19 H19B 109.5 . . ?
C18 C19 H19C 109.5 . . ?
H19A C19 H19C 109.5 . . ?
H19B C19 H19C 109.5 . . ?
C21 C20 C15 115.3(3) . . ?
C21 C20 H20A 108.4 . . ?
C15 C20 H20A 108.4 . . ?
C21 C20 H20B 108.4 . . ?
C15 C20 H20B 108.4 . . ?
H20A C20 H20B 107.5 . . ?
C20 C21 H21A 109.5 . . ?
C20 C21 H21B 109.5 . . ?
H21A C21 H21B 109.5 . . ?
C20 C21 H21C 109.5 . . ?
H21A C21 H21C 109.5 . . ?
H21B C21 H21C 109.5 . . ?
C20' C15' C16' 119.6(15) . . ?
C20' C15' C14 114.7(11) . . ?
C16' C15' C14 108.5(13) . . ?
C20' C15' H15' 104.0 . . ?
C16' C15' H15' 104.0 . . ?
C14 C15' H15' 104.0 . . ?
C17' C16' C15' 128.5(18) . . ?
C17' C16' H16C 105.2 . . ?
C15' C16' H16C 105.2 . . ?
C17' C16' H16D 105.2 . . ?
C15' C16' H16D 105.2 . . ?
H16C C16' H16D 105.9 . . ?
C16' C17' C18' 106.3(18) . . ?
C16' C17' H17C 110.5 . . ?
C18' C17' H17C 110.5 . . ?
C16' C17' H17D 110.5 . . ?
C18' C17' H17D 110.5 . . ?
H17C C17' H17D 108.7 . . ?
C19' C18' C17' 106(2) . . ?
C19' C18' H18C 110.5 . . ?
C17' C18' H18C 110.5 . . ?
C19' C18' H18D 110.5 . . ?
C17' C18' H18D 110.5 . . ?
H18C C18' H18D 108.7 . . ?
C18' C19' H19D 109.5 . . ?
C18' C19' H19E 109.5 . . ?
H19D C19' H19E 109.5 . . ?
C18' C19' H19F 109.5 . . ?
H19D C19' H19F 109.5 . . ?
H19E C19' H19F 109.5 . . ?
C21' C20' C15' 120.1(15) . . ?
C21' C20' H20C 107.3 . . ?
C15' C20' H20C 107.3 . . ?
C21' C20' H20D 107.3 . . ?
C15' C20' H20D 107.3 . . ?
H20C C20' H20D 106.9 . . ?
C20' C21' H21D 109.5 . . ?
C20' C21' H21E 109.5 . . ?
H21D C21' H21E 109.5 . . ?
C20' C21' H21F 109.5 . . ?
H21D C21' H21F 109.5 . . ?
H21E C21' H21F 109.5 . . ?

_refine_diff_density_max         0.463
_refine_diff_density_min         -0.548
_refine_diff_density_rms         0.079

_shelxl_version_number           2014/6



####################################################################### 
# 
# 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_eh_bac_2_a
_database_code_depnum_ccdc_archive 'CCDC 1032434'
_audit_update_record             
;
2014-11-03 deposited with the CCDC.
2015-03-31 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C46 H46 N2 O2'
_chemical_formula_weight         658.85

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0040 0.0020
'XDISP Program in WinGX L.Kissel & R.H.Pratt Acta Cryst A46 170 1990'
H H 0.0000 0.0000
'XDISP Program in WinGX L.Kissel & R.H.Pratt Acta Cryst A46 170 1990'
N N 0.0076 0.0040
'XDISP Program in WinGX L.Kissel & R.H.Pratt Acta Cryst A46 170 1990'
O O 0.0132 0.0074
'XDISP Program in WinGX L.Kissel & R.H.Pratt Acta Cryst A46 170 1990'

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 21/c'
_space_group_name_Hall           '-P 2ybc'

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

_cell_length_a                   15.3148(9)
_cell_length_b                   5.2027(3)
_cell_length_c                   21.5181(12)
_cell_angle_alpha                90
_cell_angle_beta                 93.605(4)
_cell_angle_gamma                90
_cell_volume                     1711.13(17)
_cell_formula_units_Z            2
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    3242
_cell_measurement_theta_min      2.86
_cell_measurement_theta_max      28.32

_exptl_crystal_description       lath
_exptl_crystal_colour            yellow
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.279
_exptl_crystal_F_000             704
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.300
_exptl_crystal_size_mid          0.060
_exptl_crystal_size_min          0.010
_exptl_absorpt_coefficient_mu    0.092
_shelx_estimated_absorpt_T_min   0.973
_shelx_estimated_absorpt_T_max   0.999
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.902
_exptl_absorpt_correction_T_max  0.999
_exptl_absorpt_process_details   'SADABS 2012/1 Bruker AXS Madison WI USA'

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.7749
_diffrn_radiation_type           synchrotron
_diffrn_source                   'Advanced Light Source station 11.3.1'
_diffrn_measurement_device_type  'Bruker APEX II CCD diffractometer'
_diffrn_measurement_method       'ω/θ scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            14784
_diffrn_reflns_av_unetI/netI     0.0646
_diffrn_reflns_av_R_equivalents  0.0624
_diffrn_reflns_limit_h_min       -19
_diffrn_reflns_limit_h_max       19
_diffrn_reflns_limit_k_min       -6
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_l_min       -27
_diffrn_reflns_limit_l_max       27
_diffrn_reflns_theta_min         2.451
_diffrn_reflns_theta_max         29.432
_diffrn_reflns_theta_full        27.706
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.996
_diffrn_reflns_point_group_measured_fraction_full 0.999
_reflns_number_total             3651
_reflns_number_gt                2417
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_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 APEX 2'
_computing_cell_refinement       'Bruker SAINT v8.34a'
_computing_data_reduction        'Bruker SAINT v8.34a'
_computing_structure_solution    'Bruker SHELXT 2014/3 (beta test)'
_computing_structure_refinement  'SHELXL-2014 (Sheldrick, 2014)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL & local programs'

_refine_special_details          
;
 All non-hydrogen atoms were refined anisotropically. Hydrogen atoms
 were place geometrically and refined using a riding model. The 
 disordered in the alkyl chain was modelled with geometrical restraints 
 (DFIX for C18' C19' of 1.54(1) and SAME for chains) and displacement
 parameter restraints (RIGU).

;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.1158P)²+1.2462P] 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         3651
_refine_ls_number_parameters     262
_refine_ls_number_restraints     64
_refine_ls_R_factor_all          0.1069
_refine_ls_R_factor_gt           0.0748
_refine_ls_wR_factor_ref         0.2409
_refine_ls_wR_factor_gt          0.2130
_refine_ls_goodness_of_fit_ref   1.050
_refine_ls_restrained_S_all      1.072
_refine_ls_shift/su_max          0.000
_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
N1 N 0.28224(14) 0.5610(4) 0.56474(9) 0.0338(5) Uani 1 1 d . . . . .
C1 C 0.32604(17) 0.7425(5) 0.59462(11) 0.0329(6) Uani 1 1 d . . . . .
C2 C 0.41593(16) 0.8094(5) 0.58753(10) 0.0296(5) Uani 1 1 d . . . . .
C3 C 0.45800(16) 0.6579(4) 0.54459(10) 0.0283(5) Uani 1 1 d . . . . .
C4 C 0.41154(16) 0.4594(4) 0.51063(10) 0.0285(5) Uani 1 1 d . . . . .
C5 C 0.32370(16) 0.4201(5) 0.52223(11) 0.0309(6) Uani 1 1 d . . . . .
C6 C 0.27616(17) 0.2242(5) 0.48966(12) 0.0350(6) Uani 1 1 d . . . . .
H6 H 0.2166 0.1956 0.4977 0.042 Uiso 1 1 calc R U . . .
C7 C 0.31433(16) 0.0765(5) 0.44706(11) 0.0336(6) Uani 1 1 d . . . . .
H7 H 0.2807 -0.0523 0.4253 0.040 Uiso 1 1 calc R U . . .
C8 C 0.40336(16) 0.1098(5) 0.43417(10) 0.0300(5) Uani 1 1 d . . . . .
C9 C 0.45149(16) 0.3021(4) 0.46660(10) 0.0278(5) Uani 1 1 d . . . . .
C10 C 0.44598(16) -0.0494(5) 0.38970(10) 0.0304(6) Uani 1 1 d . . . . .
C11 C 0.39902(18) -0.2467(5) 0.35719(11) 0.0342(6) Uani 1 1 d . . . . .
H11 H 0.3388 -0.2704 0.3639 0.041 Uiso 1 1 calc R U . . .
C12 C 0.43810(17) -0.4046(5) 0.31631(11) 0.0352(6) Uani 1 1 d . . . . .
H12 H 0.4052 -0.5354 0.2948 0.042 Uiso 1 1 calc R U . . .
C13 C 0.52601(18) -0.3724(5) 0.30657(11) 0.0355(6) Uani 1 1 d . . . . .
H13 H 0.5535 -0.4831 0.2786 0.043 Uiso 1 1 calc R U . . .
C14 C 0.57351(17) -0.1829(5) 0.33674(11) 0.0329(6) Uani 1 1 d . . . . .
H14 H 0.6336 -0.1642 0.3291 0.040 Uiso 1 1 calc R U . . .
C15 C 0.53582(16) -0.0138(5) 0.37900(10) 0.0303(6) Uani 1 1 d . . . . .
O1 O 0.28259(12) 0.8771(4) 0.63659(8) 0.0396(5) Uani 1 1 d . . . . .
C16 C 0.19180(19) 0.8237(7) 0.63987(17) 0.0597(10) Uani 1 1 d D U . . .
H16C H 0.1831 0.6352 0.6404 0.072 Uiso 0.25 1 calc R U P A 2
H16D H 0.1596 0.8921 0.6021 0.072 Uiso 0.25 1 calc R U P A 2
H16A H 0.1831 0.6488 0.6565 0.072 Uiso 0.75 1 calc R U P B 1
H16B H 0.1611 0.8363 0.5981 0.072 Uiso 0.75 1 calc R U P B 1
C17 C 0.1573(4) 1.0268(10) 0.6838(2) 0.0401(12) Uani 0.75 1 d D U P C 1
H17A H 0.1787 1.1991 0.6709 0.048 Uiso 0.75 1 calc R U P C 1
C18 C 0.0577(3) 1.0278(10) 0.6768(2) 0.0559(12) Uani 0.75 1 d D U P C 1
H18A H 0.0338 1.1054 0.7142 0.067 Uiso 0.75 1 calc R U P C 1
H18B H 0.0356 0.8494 0.6727 0.067 Uiso 0.75 1 calc R U P C 1
C19 C 0.0264(4) 1.1912(13) 0.6160(3) 0.0625(15) Uani 0.75 1 d D U P C 1
H19A H 0.0407 1.3746 0.6234 0.075 Uiso 0.75 1 calc R U P C 1
H19B H 0.0592 1.1323 0.5804 0.075 Uiso 0.75 1 calc R U P C 1
C20 C -0.0675(3) 1.1672(12) 0.5995(3) 0.0756(15) Uani 0.75 1 d D U P C 1
H20A H -0.0825 0.9842 0.5922 0.091 Uiso 0.75 1 calc R U P C 1
H20B H -0.1009 1.2295 0.6345 0.091 Uiso 0.75 1 calc R U P C 1
C21 C -0.0917(3) 1.3153(10) 0.5440(2) 0.0863(13) Uani 1 1 d D U . . .
H21D H -0.0986 1.4835 0.5238 0.129 Uiso 0.25 1 calc R U P C 2
H21E H -0.0869 1.1819 0.5122 0.129 Uiso 0.25 1 calc R U P C 2
H21F H -0.1427 1.2804 0.5680 0.129 Uiso 0.25 1 calc R U P C 2
H21A H -0.1547 1.2973 0.5336 0.129 Uiso 0.75 1 calc R U P C 1
H21B H -0.0776 1.4968 0.5515 0.129 Uiso 0.75 1 calc R U P C 1
H21C H -0.0593 1.2519 0.5093 0.129 Uiso 0.75 1 calc R U P C 1
C17' C 0.1533(12) 0.942(3) 0.6978(7) 0.047(4) Uani 0.25 1 d D U P C 2
H17B H 0.1064 0.8168 0.7075 0.057 Uiso 0.25 1 calc R U P C 2
C18' C 0.1044(11) 1.150(3) 0.6652(7) 0.082(5) Uani 0.25 1 d D U P C 2
H18C H 0.1443 1.2350 0.6372 0.098 Uiso 0.25 1 calc R U P C 2
H18D H 0.0891 1.2782 0.6966 0.098 Uiso 0.25 1 calc R U P C 2
C19' C 0.0173(13) 1.078(3) 0.6250(10) 0.084(6) Uani 0.25 1 d D U P C 2
H19C H 0.0275 0.9325 0.5967 0.101 Uiso 0.25 1 calc R U P C 2
H19D H -0.0298 1.0297 0.6523 0.101 Uiso 0.25 1 calc R U P C 2
C20' C -0.0063(9) 1.316(3) 0.5891(8) 0.072(4) Uani 0.25 1 d D U P C 2
H20C H 0.0436 1.3588 0.5639 0.086 Uiso 0.25 1 calc R U P C 2
H20D H -0.0119 1.4569 0.6194 0.086 Uiso 0.25 1 calc R U P C 2
C22 C 0.1967(2) 0.9696(7) 0.75102(14) 0.0590(9) Uani 1 1 d . . . . .
H22C H 0.2591 0.9701 0.7416 0.071 Uiso 0.25 1 calc R U P C 2
H22D H 0.1874 0.8084 0.7741 0.071 Uiso 0.25 1 calc R U P C 2
H22A H 0.1681 0.8137 0.7666 0.071 Uiso 0.75 1 calc R U P C 1
H22B H 0.2597 0.9303 0.7488 0.071 Uiso 0.75 1 calc R U P C 1
C23 C 0.1877(3) 1.1795(9) 0.79689(18) 0.0872(14) Uani 1 1 d . . . . .
H23A H 0.2289 1.1513 0.8329 0.131 Uiso 1 1 calc R U . . .
H23B H 0.2003 1.3448 0.7775 0.131 Uiso 1 1 calc R U . . .
H23C H 0.1278 1.1812 0.8105 0.131 Uiso 1 1 calc R U . . .


_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
N1 C1 1.304(3) . ?
N1 C5 1.360(3) . ?
C1 O1 1.351(3) . ?
C1 C2 1.437(3) . ?
C2 C3 1.402(3) . ?
C2 C15 1.459(3) 3_666 ?
C3 C4 1.429(3) . ?
C3 C9 1.437(3) 3_666 ?
C4 C5 1.399(3) . ?
C4 C9 1.420(3) . ?
C5 C6 1.413(3) . ?
C6 C7 1.357(4) . ?
C6 H6 0.9500 . ?
C7 C8 1.419(3) . ?
C7 H7 0.9500 . ?
C8 C9 1.402(3) . ?
C8 C10 1.451(3) . ?
C9 C3 1.437(3) 3_666 ?
C10 C11 1.413(3) . ?
C10 C15 1.421(4) . ?
C11 C12 1.368(4) . ?
C11 H11 0.9500 . ?
C12 C13 1.386(4) . ?
C12 H12 0.9500 . ?
C13 C14 1.365(3) . ?
C13 H13 0.9500 . ?
C14 C15 1.414(3) . ?
C14 H14 0.9500 . ?
C15 C2 1.459(3) 3_666 ?
O1 C16 1.424(3) . ?
C16 C17 1.534(5) . ?
C16 C17' 1.540(14) . ?
C16 H16C 0.9900 . ?
C16 H16D 0.9900 . ?
C16 H16A 0.9900 . ?
C16 H16B 0.9900 . ?
C17 C18 1.523(6) . ?
C17 C22 1.561(6) . ?
C17 H17A 1.0000 . ?
C18 C19 1.609(7) . ?
C18 H18A 0.9900 . ?
C18 H18B 0.9900 . ?
C19 C20 1.465(7) . ?
C19 H19A 0.9900 . ?
C19 H19B 0.9900 . ?
C20 C21 1.450(6) . ?
C20 H20A 0.9900 . ?
C20 H20B 0.9900 . ?
C21 C20' 1.579(12) . ?
C21 H21D 0.9800 . ?
C21 H21E 0.9800 . ?
C21 H21F 0.9800 . ?
C21 H21A 0.9800 . ?
C21 H21B 0.9800 . ?
C21 H21C 0.9800 . ?
C17' C22 1.295(16) . ?
C17' C18' 1.470(14) . ?
C17' H17B 1.0000 . ?
C18' C19' 1.587(9) . ?
C18' H18C 0.9900 . ?
C18' H18D 0.9900 . ?
C19' C20' 1.492(15) . ?
C19' H19C 0.9900 . ?
C19' H19D 0.9900 . ?
C20' H20C 0.9900 . ?
C20' H20D 0.9900 . ?
C22 C23 1.484(5) . ?
C22 H22C 0.9900 . ?
C22 H22D 0.9900 . ?
C22 H22A 0.9900 . ?
C22 H22B 0.9900 . ?
C23 H23A 0.9800 . ?
C23 H23B 0.9800 . ?
C23 H23C 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
C1 N1 C5 118.3(2) . . ?
N1 C1 O1 116.4(2) . . ?
N1 C1 C2 126.1(2) . . ?
O1 C1 C2 117.4(2) . . ?
C3 C2 C1 114.6(2) . . ?
C3 C2 C15 119.7(2) . 3_666 ?
C1 C2 C15 125.7(2) . 3_666 ?
C2 C3 C4 120.6(2) . . ?
C2 C3 C9 121.1(2) . 3_666 ?
C4 C3 C9 118.3(2) . 3_666 ?
C5 C4 C9 119.6(2) . . ?
C5 C4 C3 117.9(2) . . ?
C9 C4 C3 122.4(2) . . ?
N1 C5 C4 122.4(2) . . ?
N1 C5 C6 118.3(2) . . ?
C4 C5 C6 119.2(2) . . ?
C7 C6 C5 120.9(2) . . ?
C7 C6 H6 119.6 . . ?
C5 C6 H6 119.6 . . ?
C6 C7 C8 121.5(2) . . ?
C6 C7 H7 119.2 . . ?
C8 C7 H7 119.2 . . ?
C9 C8 C7 118.1(2) . . ?
C9 C8 C10 119.4(2) . . ?
C7 C8 C10 122.5(2) . . ?
C8 C9 C4 120.6(2) . . ?
C8 C9 C3 120.2(2) . 3_666 ?
C4 C9 C3 119.3(2) . 3_666 ?
C11 C10 C15 118.8(2) . . ?
C11 C10 C8 120.3(2) . . ?
C15 C10 C8 120.8(2) . . ?
C12 C11 C10 121.6(2) . . ?
C12 C11 H11 119.2 . . ?
C10 C11 H11 119.2 . . ?
C11 C12 C13 119.5(2) . . ?
C11 C12 H12 120.2 . . ?
C13 C12 H12 120.2 . . ?
C14 C13 C12 120.6(2) . . ?
C14 C13 H13 119.7 . . ?
C12 C13 H13 119.7 . . ?
C13 C14 C15 121.9(2) . . ?
C13 C14 H14 119.1 . . ?
C15 C14 H14 119.1 . . ?
C14 C15 C10 117.5(2) . . ?
C14 C15 C2 123.8(2) . 3_666 ?
C10 C15 C2 118.7(2) . 3_666 ?
C1 O1 C16 117.1(2) . . ?
O1 C16 C17 105.8(3) . . ?
O1 C16 C17' 112.8(8) . . ?
O1 C16 H16C 109.0 . . ?
C17' C16 H16C 109.0 . . ?
O1 C16 H16D 109.0 . . ?
C17' C16 H16D 109.0 . . ?
H16C C16 H16D 107.8 . . ?
O1 C16 H16A 110.6 . . ?
C17 C16 H16A 110.6 . . ?
O1 C16 H16B 110.6 . . ?
C17 C16 H16B 110.6 . . ?
H16A C16 H16B 108.7 . . ?
C18 C17 C16 108.9(4) . . ?
C18 C17 C22 114.8(4) . . ?
C16 C17 C22 108.1(4) . . ?
C18 C17 H17A 108.3 . . ?
C16 C17 H17A 108.3 . . ?
C22 C17 H17A 108.3 . . ?
C17 C18 C19 109.1(4) . . ?
C17 C18 H18A 109.9 . . ?
C19 C18 H18A 109.9 . . ?
C17 C18 H18B 109.9 . . ?
C19 C18 H18B 109.9 . . ?
H18A C18 H18B 108.3 . . ?
C20 C19 C18 112.9(5) . . ?
C20 C19 H19A 109.0 . . ?
C18 C19 H19A 109.0 . . ?
C20 C19 H19B 109.0 . . ?
C18 C19 H19B 109.0 . . ?
H19A C19 H19B 107.8 . . ?
C21 C20 C19 110.5(5) . . ?
C21 C20 H20A 109.6 . . ?
C19 C20 H20A 109.6 . . ?
C21 C20 H20B 109.6 . . ?
C19 C20 H20B 109.6 . . ?
H20A C20 H20B 108.1 . . ?
C20' C21 H21D 109.5 . . ?
C20' C21 H21E 109.5 . . ?
H21D C21 H21E 109.5 . . ?
C20' C21 H21F 109.5 . . ?
H21D C21 H21F 109.5 . . ?
H21E C21 H21F 109.5 . . ?
C20 C21 H21A 109.5 . . ?
C20 C21 H21B 109.5 . . ?
H21A C21 H21B 109.5 . . ?
C20 C21 H21C 109.5 . . ?
H21A C21 H21C 109.5 . . ?
H21B C21 H21C 109.5 . . ?
C22 C17' C18' 123.9(13) . . ?
C22 C17' C16 124.0(12) . . ?
C18' C17' C16 96.6(11) . . ?
C22 C17' H17B 103.0 . . ?
C18' C17' H17B 103.0 . . ?
C16 C17' H17B 103.0 . . ?
C17' C18' C19' 118.2(15) . . ?
C17' C18' H18C 107.8 . . ?
C19' C18' H18C 107.8 . . ?
C17' C18' H18D 107.8 . . ?
C19' C18' H18D 107.8 . . ?
H18C C18' H18D 107.1 . . ?
C20' C19' C18' 104.7(12) . . ?
C20' C19' H19C 110.8 . . ?
C18' C19' H19C 110.8 . . ?
C20' C19' H19D 110.8 . . ?
C18' C19' H19D 110.8 . . ?
H19C C19' H19D 108.9 . . ?
C19' C20' C21 118.8(11) . . ?
C19' C20' H20C 107.6 . . ?
C21 C20' H20C 107.6 . . ?
C19' C20' H20D 107.6 . . ?
C21 C20' H20D 107.6 . . ?
H20C C20' H20D 107.0 . . ?
C17' C22 C23 127.3(7) . . ?
C23 C22 C17 115.4(3) . . ?
C17' C22 H22C 105.5 . . ?
C23 C22 H22C 105.5 . . ?
C17' C22 H22D 105.5 . . ?
C23 C22 H22D 105.5 . . ?
H22C C22 H22D 106.1 . . ?
C23 C22 H22A 108.4 . . ?
C17 C22 H22A 108.4 . . ?
C23 C22 H22B 108.4 . . ?
C17 C22 H22B 108.4 . . ?
H22A C22 H22B 107.5 . . ?
C22 C23 H23A 109.5 . . ?
C22 C23 H23B 109.5 . . ?
H23A C23 H23B 109.5 . . ?
C22 C23 H23C 109.5 . . ?
H23A C23 H23C 109.5 . . ?
H23B C23 H23C 109.5 . . ?

_refine_diff_density_max         0.403
_refine_diff_density_min         -0.377
_refine_diff_density_rms         0.059

_shelxl_version_number           2014-3



