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

#######################################################################
#
#                 Cambridge Crystallographic Data Centre
#                                CCDC 
# 
#######################################################################
# 
#  This CIF contains data from an original supplementary publication
#  deposited with the CCDC, and may include chemical, crystal,
#  experimental, refinement, atomic coordinates,
#  anisotropic displacement parameters and molecular geometry data,
#  as required by the journal to which it was submitted.
#
#  This CIF is provided on the understanding that it is used for bona
#  fide research purposes only. It may contain copyright material
#  of the CCDC or of third parties, and may not be copied or further
#  disseminated in any form, whether machine-readable or not,
#  except for the purpose of generating routine backup copies
#  on your local computer system.
# 
#  For further information on the CCDC, data deposition and
#  data retrieval see:
#                         www.ccdc.cam.ac.uk
#
#  Bona fide researchers may freely download Mercury and enCIFer
#  from this site to visualise CIF-encoded structures and 
#  to carry out CIF format checking respectively.
#
data_Compound_2b

_audit_creation_method           
'SHELXL-2012 & Rigaku CrystalClear-SM Expert 2.0 r4'

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'
F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_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                   15.9782(6)
_cell_length_b                   7.2762(2)
_cell_length_c                   13.9814(6)
_cell_angle_alpha                90
_cell_angle_beta                 102.701(2)
_cell_angle_gamma                90
_cell_volume                     1585.71(10)
_cell_formula_units_Z            2
_cell_measurement_temperature    123(2)
_cell_measurement_reflns_used    8235
_cell_measurement_theta_min      1.8
_cell_measurement_theta_max      27.5

_exptl_crystal_F_000             688
_exptl_crystal_description       Prism
_exptl_crystal_colour            Orange
_exptl_crystal_size_max          0.35
_exptl_crystal_size_mid          0.28
_exptl_crystal_size_min          0.10
_chemical_formula_weight         668.68
_chemical_formula_analytical     ?
_chemical_formula_sum            'C44 H26 F6 '
_exptl_absorpt_coefficient_mu    0.105
_exptl_absorpt_correction_type   Numerical
_exptl_absorpt_correction_T_max  0.992
_exptl_absorpt_correction_T_min  0.971
_exptl_absorpt_process_details   
;
'CrystalClear-SM Expert 2.0 r4 (Rigaku, 2009)'
;

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      123(2)
_diffrn_source_power             1.8
_diffrn_source_voltage           50.0
_diffrn_source_current           35.0
_diffrn_radiation_wavelength     0.71075
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  'Graphite Monochromator'
_diffrn_measurement_device       'Crystal Goniometer'
_diffrn_measurement_device_type  'Rigaku RAXIS II'
_diffrn_measurement_specimen_support Fiber
_diffrn_detector                 'Curved image plate'
_diffrn_measurement_method       'profile data from ω-scans'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_reflns_number            15137
_diffrn_reflns_av_unetI/netI     0.0494
_diffrn_reflns_av_R_equivalents  0.0505
_diffrn_reflns_limit_h_min       -20
_diffrn_reflns_limit_h_max       20
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_theta_min         2.987
_diffrn_reflns_theta_max         27.502
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measured_fraction_theta_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_point_group_measured_fraction_full 0.997
_reflns_number_total             3643
_reflns_number_gt                3222
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_computing_data_collection       
;
CrystalClear-SM Expert 2.0 r4 (Rigaku, 2009)
;
_computing_cell_refinement       
;
CrystalClear-SM Expert 2.0 r4 (Rigaku, 2009)
;
_computing_data_reduction        
;
CrystalClear-SM Expert 2.0 r4 (Rigaku, 2009)
;
_computing_structure_solution    'SHELXS-2013 (Sheldrick, 2013)'
_computing_structure_refinement  'SHELXL-2013 (Sheldrick, 2013)'
_computing_molecular_graphics    ?
_computing_publication_material  ?

_refine_special_details          
;
'Refinement of F² against ALL reflections.  The weighted R-factor wR and
 goodness of fit S are based on F², conventional R-factors R are based
 on F, with F set to zero for negative F². The threshold expression of
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is
 not relevant to the choice of reflections for refinement.  R-factors based
 on F² are statistically about twice as large as those based on F, and R-
 factors based on ALL data will be even larger.'
;
_diffrn_measurement_details      
;
scan:
	Number of images: 50
	           Slice: 20.0000 - 170.0000
	     Image width: 3.0000
	        Exp time: 360.0000
	   Rotation axis: Omega
	           Omega: 0.0000
	             Chi: 30.0000
	             Phi: 180.0000
	             XTD: 127.4000
	          2theta: -0.0229
scan:
	Number of images: 25
	           Slice: 95.0000 - 170.0000
	     Image width: 3.0000
	        Exp time: 360.0000
	   Rotation axis: Omega
	           Omega: 0.0000
	             Chi: 0.0000
	             Phi: 0.0000
	             XTD: 127.4000
	          2theta: -0.0229
;
_diffrn_orient_matrix_UB_11      0.001006
_diffrn_orient_matrix_UB_12      -0.064417
_diffrn_orient_matrix_UB_13      -0.034999
_diffrn_orient_matrix_UB_21      -0.106536
_diffrn_orient_matrix_UB_22      -0.042728
_diffrn_orient_matrix_UB_23      0.075581
_diffrn_orient_matrix_UB_31      -0.039335
_diffrn_orient_matrix_UB_32      0.010294
_diffrn_orient_matrix_UB_33      -0.049625
_diffrn_orient_matrix_type       d*Trek

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0244P)²+1.4827P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     SHELXL
_refine_ls_extinction_coef       0.0048(11)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         3643
_refine_ls_number_parameters     197
_refine_ls_number_restraints     183
_refine_ls_R_factor_all          0.0763
_refine_ls_R_factor_gt           0.0659
_refine_ls_wR_factor_ref         0.1354
_refine_ls_wR_factor_gt          0.1299
_refine_ls_goodness_of_fit_ref   1.108
_refine_ls_restrained_S_all      1.110
_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
C1 C 0.18597(5) -0.14438(12) 0.97899(6) 0.0226(4) Uani 1 1 d G U . . .
C2 C 0.24601(6) -0.24679(9) 1.04470(6) 0.0284(5) Uani 1 1 d G U . . .
H2 H 0.2288 -0.3170 1.0925 0.034 Uiso 1 1 calc R U . . .
C3 C 0.33174(6) -0.24421(11) 1.03891(7) 0.0359(5) Uani 1 1 d G U . . .
H3 H 0.3719 -0.3127 1.0829 0.043 Uiso 1 1 calc R U . . .
C4 C 0.35743(6) -0.13922(15) 0.96741(7) 0.0390(6) Uani 1 1 d G U . . .
H4 H 0.4148 -0.1375 0.9635 0.047 Uiso 1 1 calc R U . . .
C5 C 0.29740(7) -0.03680(15) 0.90170(6) 0.0361(5) Uani 1 1 d G U . . .
H5 H 0.3146 0.0335 0.8539 0.043 Uiso 1 1 calc R U . . .
C6 C 0.21167(6) -0.03938(14) 0.90749(5) 0.0280(4) Uani 1 1 d G U . . .
H6 H 0.1715 0.0291 0.8635 0.034 Uiso 1 1 calc R U . . .
C7 C 0.18603(5) 0.12510(12) 1.12563(6) 0.0221(4) Uani 1 1 d G U . . .
C8 C 0.20497(6) 0.02091(13) 1.21099(6) 0.0260(4) Uani 1 1 d G U . . .
H8 H 0.1618 -0.0446 1.2309 0.031 Uiso 1 1 calc R U . . .
C9 C 0.28849(7) 0.01456(14) 1.26666(5) 0.0301(5) Uani 1 1 d G U . . .
H9 H 0.3012 -0.0552 1.3238 0.036 Uiso 1 1 calc R U . . .
C10 C 0.35306(5) 0.11241(14) 1.23697(6) 0.0309(5) Uani 1 1 d G U . . .
C11 C 0.33412(6) 0.21660(11) 1.15161(7) 0.0304(5) Uani 1 1 d G U . . .
H11 H 0.3773 0.2821 1.1317 0.036 Uiso 1 1 calc R U . . .
C12 C 0.25060(6) 0.22295(8) 1.09593(6) 0.0261(4) Uani 1 1 d G U . . .
H12 H 0.2379 0.2927 1.0388 0.031 Uiso 1 1 calc R U . . .
C13 C 0.09073(11) -0.1505(3) 0.97772(14) 0.0211(4) Uani 1 1 d . U . . .
C14 C 0.04716(11) -0.0020(3) 1.01322(13) 0.0200(4) Uani 1 1 d . U . . .
C15 C 0.09214(11) 0.1403(3) 1.07337(14) 0.0202(4) Uani 1 1 d . U . . .
C16 C 0.04793(12) 0.2929(3) 1.09877(14) 0.0209(4) Uani 1 1 d . U . . .
C17 C 0.09151(13) 0.4412(3) 1.15732(14) 0.0240(4) Uani 1 1 d . U . . .
H17 H 0.1510 0.4380 1.1771 0.029 Uiso 1 1 calc R U . . .
C18 C 0.04821(13) 0.5857(3) 1.18443(15) 0.0269(4) Uani 1 1 d . U . . .
H18 H 0.0783 0.6800 1.2218 0.032 Uiso 1 1 calc R U . . .
C19 C -0.04255(13) 0.5939(3) 1.15618(15) 0.0270(4) Uani 1 1 d . U . . .
H19 H -0.0717 0.6945 1.1739 0.032 Uiso 1 1 calc R U . . .
C20 C -0.08696(13) 0.4547(3) 1.10322(14) 0.0246(4) Uani 1 1 d . U . . .
H20 H -0.1465 0.4604 1.0868 0.029 Uiso 1 1 calc R U . . .
C21 C 0.04465(12) -0.2987(3) 0.92823(14) 0.0211(4) Uani 1 1 d . U . . .
C22 C 0.44252(14) 0.1128(3) 1.2993(2) 0.0402(6) Uani 1 1 d . U . . .
F1 F 0.46000(10) -0.0327(3) 1.35651(16) 0.0779(7) Uani 1 1 d . U . . .
F2 F 0.50261(9) 0.1150(3) 1.24718(15) 0.0735(6) Uani 1 1 d . U . . .
F3 F 0.45791(10) 0.2595(3) 1.35632(16) 0.0861(8) Uani 1 1 d . 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
C1 C2 1.3900 . ?
C1 C6 1.3900 . ?
C1 C13 1.5186(19) . ?
C2 C3 1.3900 . ?
C3 C4 1.3900 . ?
C4 C5 1.3900 . ?
C5 C6 1.3900 . ?
C7 C8 1.3900 . ?
C7 C12 1.3900 . ?
C7 C15 1.5213(19) . ?
C8 C9 1.3900 . ?
C9 C10 1.3900 . ?
C10 C11 1.3900 . ?
C10 C22 1.501(2) . ?
C11 C12 1.3900 . ?
C13 C21 1.400(3) . ?
C13 C14 1.432(3) . ?
C14 C15 1.425(3) . ?
C14 C14 1.471(3) 3_557 ?
C15 C16 1.403(3) . ?
C16 C17 1.438(3) . ?
C16 C21 1.445(3) 3_557 ?
C17 C18 1.358(3) . ?
C18 C19 1.418(3) . ?
C19 C20 1.359(3) . ?
C20 C21 1.438(3) 3_557 ?
C21 C20 1.438(3) 3_557 ?
C21 C16 1.445(3) 3_557 ?
C22 F1 1.320(3) . ?
C22 F3 1.323(3) . ?
C22 F2 1.327(3) . ?

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 120.0 . . ?
C2 C1 C13 122.43(9) . . ?
C6 C1 C13 117.47(9) . . ?
C1 C2 C3 120.0 . . ?
C4 C3 C2 120.0 . . ?
C5 C4 C3 120.0 . . ?
C4 C5 C6 120.0 . . ?
C5 C6 C1 120.0 . . ?
C8 C7 C12 120.0 . . ?
C8 C7 C15 117.22(9) . . ?
C12 C7 C15 122.53(9) . . ?
C9 C8 C7 120.0 . . ?
C8 C9 C10 120.0 . . ?
C11 C10 C9 120.0 . . ?
C11 C10 C22 119.80(12) . . ?
C9 C10 C22 120.14(12) . . ?
C12 C11 C10 120.0 . . ?
C11 C12 C7 120.0 . . ?
C21 C13 C14 120.63(16) . . ?
C21 C13 C1 116.43(15) . . ?
C14 C13 C1 122.43(15) . . ?
C15 C14 C13 122.16(16) . . ?
C15 C14 C14 119.3(2) . 3_557 ?
C13 C14 C14 118.5(2) . 3_557 ?
C16 C15 C14 120.52(16) . . ?
C16 C15 C7 115.72(15) . . ?
C14 C15 C7 123.16(15) . . ?
C15 C16 C17 122.02(17) . . ?
C15 C16 C21 120.05(17) . 3_557 ?
C17 C16 C21 117.80(17) . 3_557 ?
C18 C17 C16 121.82(18) . . ?
C17 C18 C19 120.50(19) . . ?
C20 C19 C18 120.00(19) . . ?
C19 C20 C21 122.04(18) . 3_557 ?
C13 C21 C20 121.83(17) . 3_557 ?
C13 C21 C16 120.23(17) . 3_557 ?
C20 C21 C16 117.80(17) 3_557 3_557 ?
F1 C22 F3 107.2(2) . . ?
F1 C22 F2 105.1(2) . . ?
F3 C22 F2 105.1(2) . . ?
F1 C22 C10 113.44(19) . . ?
F3 C22 C10 112.24(18) . . ?
F2 C22 C10 113.1(2) . . ?

_refine_diff_density_max         0.370
_refine_diff_density_min         -0.297
_refine_diff_density_rms         0.048

_shelxl_version_number           2013-3
_database_code_depnum_ccdc_archive 'CCDC 970522'
#######################################################################
#
#                 Cambridge Crystallographic Data Centre
#                                CCDC 
# 
#######################################################################
# 
#  This CIF contains data from an original supplementary publication
#  deposited with the CCDC, and may include chemical, crystal,
#  experimental, refinement, atomic coordinates,
#  anisotropic displacement parameters and molecular geometry data,
#  as required by the journal to which it was submitted.
#
#  This CIF is provided on the understanding that it is used for bona
#  fide research purposes only. It may contain copyright material
#  of the CCDC or of third parties, and may not be copied or further
#  disseminated in any form, whether machine-readable or not,
#  except for the purpose of generating routine backup copies
#  on your local computer system.
# 
#  For further information on the CCDC, data deposition and
#  data retrieval see:
#                         www.ccdc.cam.ac.uk
#
#  Bona fide researchers may freely download Mercury and enCIFer
#  from this site to visualise CIF-encoded structures and 
#  to carry out CIF format checking respectively.
#
data_Compound_2c

_audit_creation_method           
'SHELXL-2012 & Rigaku CrystalClear-SM Expert 2.0 r4'

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'

_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                   14.9125(6)
_cell_length_b                   7.1151(2)
_cell_length_c                   14.4263(4)
_cell_angle_alpha                90
_cell_angle_beta                 98.099(2)
_cell_angle_gamma                90
_cell_volume                     1515.42(9)
_cell_formula_units_Z            2
_cell_measurement_temperature    120(2)
_cell_measurement_reflns_used    4325
_cell_measurement_theta_min      1.8
_cell_measurement_theta_max      27.5

_exptl_crystal_F_000             608
_exptl_crystal_description       Prism
_exptl_crystal_colour            Red
_exptl_crystal_size_max          0.34
_exptl_crystal_size_mid          0.34
_exptl_crystal_size_min          0.06
_chemical_formula_weight         582.70
_chemical_formula_analytical     ?
_chemical_formula_sum            'C44 H26 N2 '
_exptl_absorpt_coefficient_mu    0.074
_exptl_absorpt_correction_type   Numerical
_exptl_absorpt_correction_T_max  0.996
_exptl_absorpt_correction_T_min  0.983
_exptl_absorpt_process_details   
;
'CrystalClear-SM Expert 2.0 r4 (Rigaku, 2009)'
;

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      120(2)
_diffrn_source_power             1.8
_diffrn_source_voltage           50.0
_diffrn_source_current           35.0
_diffrn_radiation_wavelength     0.71075
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  'Graphite Monochromator'
_diffrn_measurement_device       'Crystal Goniometer'
_diffrn_measurement_device_type  'Rigaku RAXIS II'
_diffrn_measurement_specimen_support Fiber
_diffrn_detector                 'Curved image plate'
_diffrn_measurement_method       'profile data from ω-scans'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_reflns_number            14179
_diffrn_reflns_av_unetI/netI     0.0947
_diffrn_reflns_av_R_equivalents  0.1059
_diffrn_reflns_limit_h_min       -18
_diffrn_reflns_limit_h_max       19
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_theta_min         3.178
_diffrn_reflns_theta_max         27.511
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.994
_diffrn_measured_fraction_theta_full 0.994
_diffrn_reflns_Laue_measured_fraction_max 0.994
_diffrn_reflns_Laue_measured_fraction_full 0.994
_diffrn_reflns_point_group_measured_fraction_max 0.994
_diffrn_reflns_point_group_measured_fraction_full 0.994
_reflns_number_total             3472
_reflns_number_gt                2336
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .
_computing_data_collection       
;
CrystalClear-SM Expert 2.0 r4 (Rigaku, 2009)
;
_computing_cell_refinement       
;
CrystalClear-SM Expert 2.0 r4 (Rigaku, 2009)
;
_computing_data_reduction        
;
CrystalClear-SM Expert 2.0 r4 (Rigaku, 2009)
;
_computing_structure_solution    'SHELXS-2013 (Sheldrick, 2013)'
_computing_structure_refinement  'SHELXL-2013 (Sheldrick, 2013)'
_computing_molecular_graphics    ?
_computing_publication_material  ?

_refine_special_details          
;
'Refinement of F² against ALL reflections.  The weighted R-factor wR and
 goodness of fit S are based on F², conventional R-factors R are based
 on F, with F set to zero for negative F². The threshold expression of
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is
 not relevant to the choice of reflections for refinement.  R-factors based
 on F² are statistically about twice as large as those based on F, and R-
 factors based on ALL data will be even larger.'
;
_diffrn_measurement_details      
;
scan:
	Number of images: 24
	           Slice: 50.0000 - 170.0000
	     Image width: 5.0000
	        Exp time: 180.0000
	   Rotation axis: Omega
	           Omega: 0.0000
	             Chi: 45.0000
	             Phi: 90.0000
	             XTD: 127.4000
	          2theta: -0.0386
scan:
	Number of images: 21
	           Slice: 72.0000 - 177.0000
	     Image width: 5.0000
	        Exp time: 180.0000
	   Rotation axis: Omega
	           Omega: 0.0000
	             Chi: 0.0000
	             Phi: 0.0000
	             XTD: 127.4000
	          2theta: -0.0386

;
_diffrn_orient_matrix_UB_11      -0.042459
_diffrn_orient_matrix_UB_12      0.054924
_diffrn_orient_matrix_UB_13      -0.009102
_diffrn_orient_matrix_UB_21      0.111404
_diffrn_orient_matrix_UB_22      0.085638
_diffrn_orient_matrix_UB_23      -0.002912
_diffrn_orient_matrix_UB_31      -0.001565
_diffrn_orient_matrix_UB_32      -0.000267
_diffrn_orient_matrix_UB_33      -0.067715
_diffrn_orient_matrix_type       d*Trek

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0408P)²+0.4282P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     SHELXL
_refine_ls_extinction_coef       0.033(4)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         3472
_refine_ls_number_parameters     179
_refine_ls_number_restraints     171
_refine_ls_R_factor_all          0.1016
_refine_ls_R_factor_gt           0.0665
_refine_ls_wR_factor_ref         0.1538
_refine_ls_wR_factor_gt          0.1352
_refine_ls_goodness_of_fit_ref   1.038
_refine_ls_restrained_S_all      1.017
_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
N N 0.53603(13) 0.6012(3) 0.78506(14) 0.0476(6) Uani 1 1 d . U . . .
C1 C 0.19763(5) 0.36233(14) 0.46089(6) 0.0313(5) Uani 1 1 d G U . . .
C2 C 0.26292(7) 0.26398(10) 0.52005(6) 0.0352(5) Uani 1 1 d G U . . .
H2 H 0.2458 0.1913 0.5700 0.042 Uiso 1 1 calc R U . . .
C3 C 0.35321(7) 0.27196(13) 0.50618(6) 0.0409(6) Uani 1 1 d G U . . .
H3 H 0.3978 0.2047 0.5466 0.049 Uiso 1 1 calc R U . . .
C4 C 0.37821(6) 0.37828(18) 0.43315(6) 0.0453(6) Uani 1 1 d G U . . .
H4 H 0.4399 0.3837 0.4237 0.054 Uiso 1 1 calc R U . . .
C5 C 0.31292(7) 0.47663(17) 0.37398(5) 0.0415(6) Uani 1 1 d G U . . .
H5 H 0.3300 0.5493 0.3241 0.050 Uiso 1 1 calc R U . . .
C6 C 0.22263(7) 0.46866(16) 0.38785(5) 0.0354(5) Uani 1 1 d G U . . .
H6 H 0.1780 0.5359 0.3474 0.042 Uiso 1 1 calc R U . . .
C7 C 0.19459(5) 0.62948(14) 0.60653(6) 0.0312(5) Uani 1 1 d G U . . .
C8 C 0.21545(7) 0.51868(16) 0.68599(5) 0.0346(5) Uani 1 1 d G U . . .
H8 H 0.1693 0.4479 0.7090 0.042 Uiso 1 1 calc R U . . .
C9 C 0.30387(7) 0.51147(16) 0.73178(4) 0.0369(5) Uani 1 1 d G U . . .
H9 H 0.3181 0.4357 0.7861 0.044 Uiso 1 1 calc R U . . .
C10 C 0.37142(6) 0.61508(16) 0.69811(6) 0.0341(5) Uani 1 1 d G U . . .
C11 C 0.35056(7) 0.72589(12) 0.61865(6) 0.0353(5) Uani 1 1 d G U . . .
H11 H 0.3967 0.7967 0.5956 0.042 Uiso 1 1 calc R U . . .
C12 C 0.26214(7) 0.73309(10) 0.57286(6) 0.0336(5) Uani 1 1 d G U . . .
H12 H 0.2479 0.8088 0.5185 0.040 Uiso 1 1 calc R U . . .
C13 C 0.09717(13) 0.3523(3) 0.46884(13) 0.0293(5) Uani 1 1 d . U . . .
C14 C 0.04965(13) 0.4988(3) 0.50865(13) 0.0288(5) Uani 1 1 d . U . . .
C15 C 0.09566(13) 0.6437(3) 0.56464(13) 0.0295(5) Uani 1 1 d . U . . .
C16 C 0.04778(14) 0.7966(3) 0.59454(13) 0.0300(5) Uani 1 1 d . U . . .
C17 C 0.09275(15) 0.9483(3) 0.64913(14) 0.0349(5) Uani 1 1 d . U . . .
H17 H 0.1570 0.9483 0.6624 0.042 Uiso 1 1 calc R U . . .
C18 C 0.04552(15) 1.0906(3) 0.68191(14) 0.0360(5) Uani 1 1 d . U . . .
H18 H 0.0770 1.1885 0.7176 0.043 Uiso 1 1 calc R U . . .
C19 C -0.05015(15) 1.0946(3) 0.66346(14) 0.0359(5) Uani 1 1 d . U . . .
H19 H -0.0826 1.1959 0.6859 0.043 Uiso 1 1 calc R U . . .
C20 C -0.09562(15) 0.9540(3) 0.61375(14) 0.0340(5) Uani 1 1 d . U . . .
H20 H -0.1599 0.9578 0.6029 0.041 Uiso 1 1 calc R U . . .
C21 C -0.04969(14) 0.7999(3) 0.57710(13) 0.0297(5) Uani 1 1 d . U . . .
C22 C 0.46299(15) 0.6077(3) 0.74632(15) 0.0389(6) Uani 1 1 d . 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
N C22 1.153(3) . ?
C1 C2 1.3900 . ?
C1 C6 1.3900 . ?
C1 C13 1.520(2) . ?
C2 C3 1.3900 . ?
C3 C4 1.3900 . ?
C4 C5 1.3900 . ?
C5 C6 1.3900 . ?
C7 C8 1.3900 . ?
C7 C12 1.3900 . ?
C7 C15 1.517(2) . ?
C8 C9 1.3900 . ?
C9 C10 1.3900 . ?
C10 C11 1.3900 . ?
C10 C22 1.443(2) . ?
C11 C12 1.3900 . ?
C13 C21 1.407(3) 3_566 ?
C13 C14 1.426(3) . ?
C14 C15 1.425(3) . ?
C14 C14 1.467(4) 3_566 ?
C15 C16 1.402(3) . ?
C16 C21 1.440(3) . ?
C16 C17 1.444(3) . ?
C17 C18 1.356(3) . ?
C18 C19 1.414(3) . ?
C19 C20 1.355(3) . ?
C20 C21 1.433(3) . ?
C21 C13 1.407(3) 3_566 ?

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 120.0 . . ?
C2 C1 C13 122.85(9) . . ?
C6 C1 C13 117.08(9) . . ?
C3 C2 C1 120.0 . . ?
C2 C3 C4 120.0 . . ?
C5 C4 C3 120.0 . . ?
C4 C5 C6 120.0 . . ?
C5 C6 C1 120.0 . . ?
C8 C7 C12 120.0 . . ?
C8 C7 C15 117.30(10) . . ?
C12 C7 C15 122.51(10) . . ?
C9 C8 C7 120.0 . . ?
C10 C9 C8 120.0 . . ?
C11 C10 C9 120.0 . . ?
C11 C10 C22 120.30(12) . . ?
C9 C10 C22 119.70(12) . . ?
C10 C11 C12 120.0 . . ?
C11 C12 C7 120.0 . . ?
C21 C13 C14 120.42(18) 3_566 . ?
C21 C13 C1 115.88(17) 3_566 . ?
C14 C13 C1 123.16(17) . . ?
C15 C14 C13 122.04(18) . . ?
C15 C14 C14 118.8(2) . 3_566 ?
C13 C14 C14 119.2(2) . 3_566 ?
C16 C15 C14 120.70(18) . . ?
C16 C15 C7 115.98(16) . . ?
C14 C15 C7 122.75(17) . . ?
C15 C16 C21 120.25(18) . . ?
C15 C16 C17 122.01(19) . . ?
C21 C16 C17 117.59(19) . . ?
C18 C17 C16 121.6(2) . . ?
C17 C18 C19 120.6(2) . . ?
C20 C19 C18 120.1(2) . . ?
C19 C20 C21 122.0(2) . . ?
C13 C21 C20 121.84(19) 3_566 . ?
C13 C21 C16 119.91(19) 3_566 . ?
C20 C21 C16 118.09(19) . . ?
N C22 C10 179.7(3) . . ?

_refine_diff_density_max         0.323
_refine_diff_density_min         -0.193
_refine_diff_density_rms         0.046

_shelxl_version_number           2013-3
_database_code_depnum_ccdc_archive 'CCDC 970523'
#######################################################################
#
#                 Cambridge Crystallographic Data Centre
#                                CCDC 
# 
#######################################################################
# 
#  This CIF contains data from an original supplementary publication
#  deposited with the CCDC, and may include chemical, crystal,
#  experimental, refinement, atomic coordinates,
#  anisotropic displacement parameters and molecular geometry data,
#  as required by the journal to which it was submitted.
#
#  This CIF is provided on the understanding that it is used for bona
#  fide research purposes only. It may contain copyright material
#  of the CCDC or of third parties, and may not be copied or further
#  disseminated in any form, whether machine-readable or not,
#  except for the purpose of generating routine backup copies
#  on your local computer system.
# 
#  For further information on the CCDC, data deposition and
#  data retrieval see:
#                         www.ccdc.cam.ac.uk
#
#  Bona fide researchers may freely download Mercury and enCIFer
#  from this site to visualise CIF-encoded structures and 
#  to carry out CIF format checking respectively.
#
data_Compound_2d

_audit_creation_method           
'SHELXL-2012 & Rigaku CrystalClear-SM Expert 2.0 r4'

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'
S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_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                   13.5679(5)
_cell_length_b                   7.0143(2)
_cell_length_c                   14.3020(7)
_cell_angle_alpha                90
_cell_angle_beta                 103.954(2)
_cell_angle_gamma                90
_cell_volume                     1320.94(9)
_cell_formula_units_Z            2
_cell_measurement_temperature    120(2)
_cell_measurement_reflns_used    5373
_cell_measurement_theta_min      2.4
_cell_measurement_theta_max      27.5

_exptl_crystal_F_000             568
_exptl_crystal_description       Prism
_exptl_crystal_colour            Red
_exptl_crystal_size_max          0.35
_exptl_crystal_size_mid          0.14
_exptl_crystal_size_min          0.10
_chemical_formula_weight         544.73
_chemical_formula_analytical     ?
_chemical_formula_sum            'C38 H24 S2 '
_exptl_absorpt_coefficient_mu    0.23
_exptl_absorpt_correction_type   Numerical
_exptl_absorpt_correction_T_max  0.982
_exptl_absorpt_correction_T_min  0.948
_exptl_absorpt_process_details   
;
'CrystalClear-SM Expert 2.0 r4 (Rigaku, 2009)'
;
_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      120(2)
_diffrn_source_power             1.8
_diffrn_source_voltage           50.0
_diffrn_source_current           35.0
_diffrn_radiation_wavelength     0.71075
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  'Graphite Monochromator'
_diffrn_measurement_device       'Crystal Goniometer'
_diffrn_measurement_device_type  'Rigaku RAXIS II'
_diffrn_measurement_specimen_support Fiber
_diffrn_detector                 'Curved image plate'
_diffrn_measurement_method       'profile data from ω-scans'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_reflns_number            12413
_diffrn_reflns_av_unetI/netI     0.0867
_diffrn_reflns_av_R_equivalents  0.0890
_diffrn_reflns_limit_h_min       -17
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_theta_min         2.935
_diffrn_reflns_theta_max         27.493
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measured_fraction_theta_full 0.995
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_Laue_measured_fraction_full 0.995
_diffrn_reflns_point_group_measured_fraction_max 0.996
_diffrn_reflns_point_group_measured_fraction_full 0.995
_reflns_number_total             3015
_reflns_number_gt                2352
_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       
;
CrystalClear-SM Expert 2.0 r4 (Rigaku, 2009)
;
_computing_cell_refinement       
;
CrystalClear-SM Expert 2.0 r4 (Rigaku, 2009)
;
_computing_data_reduction        
;
CrystalClear-SM Expert 2.0 r4 (Rigaku, 2009)
;
_computing_structure_solution    'SHELXS-2013 (Sheldrick, 2013)'
_computing_structure_refinement  'SHELXL-2013 (Sheldrick, 2013)'
_computing_molecular_graphics    ?
_computing_publication_material  ?

_refine_special_details          
;
'Refinement of F² against ALL reflections.  The weighted R-factor wR and
 goodness of fit S are based on F², conventional R-factors R are based
 on F, with F set to zero for negative F². The threshold expression of
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is
 not relevant to the choice of reflections for refinement.  R-factors based
 on F² are statistically about twice as large as those based on F, and R-
 factors based on ALL data will be even larger.'
;
_diffrn_measurement_details      
;
scan:
	Number of images: 37
	           Slice: 20.0000 - 170.0000
	     Image width: 4.0000
	        Exp time: 180.0000
	   Rotation axis: Omega
	           Omega: 0.0000
	             Chi: 45.0000
	             Phi: 0.0000
	             XTD: 127.4000
	          2theta: -0.0285
scan:
	Number of images: 19
	           Slice: 94.0000 - 170.0000
	     Image width: 4.0000
	        Exp time: 180.0000
	   Rotation axis: Omega
	           Omega: 0.0000
	             Chi: 0.0000
	             Phi: 0.0000
	             XTD: 127.4000
	          2theta: -0.0285

;
_diffrn_orient_matrix_UB_11      -0.010133
_diffrn_orient_matrix_UB_12      0.002982
_diffrn_orient_matrix_UB_13      0.075206
_diffrn_orient_matrix_UB_21      -0.139237
_diffrn_orient_matrix_UB_22      0.023461
_diffrn_orient_matrix_UB_23      -0.019691
_diffrn_orient_matrix_UB_31      -0.014092
_diffrn_orient_matrix_UB_32      -0.068230
_diffrn_orient_matrix_UB_33      0.018351
_diffrn_orient_matrix_type       d*Trek

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0392P)²+0.9584P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     SHELXL
_refine_ls_extinction_coef       0.014(3)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         3015
_refine_ls_number_parameters     186
_refine_ls_number_restraints     192
_refine_ls_R_factor_all          0.0897
_refine_ls_R_factor_gt           0.0687
_refine_ls_wR_factor_ref         0.1625
_refine_ls_wR_factor_gt          0.1501
_refine_ls_goodness_of_fit_ref   1.100
_refine_ls_restrained_S_all      1.073
_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
C1 C 0.22060(9) 0.6473(2) 0.62124(11) 0.0284(6) Uani 1 1 d G U . . .
C2 C 0.28999(12) 0.7544(2) 0.58608(10) 0.0315(6) Uani 1 1 d G U . . .
H2 H 0.2686 0.8208 0.5268 0.038 Uiso 1 1 calc R U . . .
C3 C 0.39075(10) 0.7643(3) 0.63771(13) 0.0398(7) Uani 1 1 d G U . . .
H3 H 0.4382 0.8375 0.6137 0.048 Uiso 1 1 calc R U . . .
C4 C 0.42212(9) 0.6671(3) 0.72450(12) 0.0455(8) Uani 1 1 d G U . . .
H4 H 0.4910 0.6738 0.7598 0.055 Uiso 1 1 calc R U . . .
C5 C 0.35273(12) 0.5599(3) 0.75967(10) 0.0438(7) Uani 1 1 d G U . . .
H5 H 0.3742 0.4935 0.8190 0.053 Uiso 1 1 calc R U . . .
C6 C 0.25197(11) 0.5500(2) 0.70804(11) 0.0311(6) Uani 1 1 d G U . . .
H6 H 0.2046 0.4768 0.7321 0.037 Uiso 1 1 calc R U . . .
C11 C 0.10722(17) 0.6512(3) 0.57245(17) 0.0253(5) Uani 1 1 d . U . . .
C12 C 0.05572(17) 0.5009(3) 0.51275(17) 0.0245(5) Uani 1 1 d . U . . .
C13 C 0.10892(17) 0.3539(3) 0.47691(17) 0.0256(5) Uani 1 1 d D U . . .
C14 C 0.05618(18) 0.1986(4) 0.42570(17) 0.0263(5) Uani 1 1 d . U . . .
C15 C 0.10836(19) 0.0441(4) 0.39208(18) 0.0289(6) Uani 1 1 d . U . . .
H15 H 0.1804 0.0456 0.4059 0.035 Uiso 1 1 calc R U . . .
C16 C 0.0574(2) -0.1031(4) 0.34133(18) 0.0324(6) Uani 1 1 d . U . . .
H16 H 0.0941 -0.2043 0.3213 0.039 Uiso 1 1 calc R U . . .
C17 C -0.0496(2) -0.1076(4) 0.31794(18) 0.0330(6) Uani 1 1 d . U . . .
H17 H -0.0847 -0.2120 0.2826 0.040 Uiso 1 1 calc R U . . .
C18 C 0.05252(18) 0.8045(4) 0.59891(17) 0.0269(5) Uani 1 1 d . U . . .
C19 C 0.10295(19) 0.9629(4) 0.65413(18) 0.0303(6) Uani 1 1 d . U . . .
H19 H 0.1751 0.9667 0.6715 0.036 Uiso 1 1 calc R U . . .
S1A S 0.25983(10) 0.4734(2) 0.39012(8) 0.0348(3) Uani 0.784(3) 1 d D U P A 1
C7A C 0.2200(4) 0.3572(16) 0.4795(8) 0.0271(15) Uani 0.784(3) 1 d D U P A 1
C8A C 0.2988(9) 0.270(2) 0.5424(11) 0.0413(12) Uani 0.784(3) 1 d D U P A 1
H8A H 0.2911 0.2010 0.5974 0.050 Uiso 0.784(3) 1 calc R U P A 1
C9A C 0.3937(5) 0.2918(10) 0.5175(4) 0.0359(10) Uani 0.784(3) 1 d D U P A 1
H9A H 0.4557 0.2381 0.5530 0.043 Uiso 0.784(3) 1 calc R U P A 1
C10A C 0.3842(3) 0.4008(9) 0.4357(4) 0.0377(10) Uani 0.784(3) 1 d D U P A 1
H10A H 0.4390 0.4322 0.4077 0.045 Uiso 0.784(3) 1 calc R U P A 1
C7B C 0.2187(12) 0.381(7) 0.485(3) 0.0271(15) Uani 0.216(3) 1 d D U P A 2
C8B C 0.2545(16) 0.447(4) 0.4111(16) 0.0348(3) Uani 0.216(3) 1 d D U P A 2
H8B H 0.2100 0.5040 0.3569 0.042 Uiso 0.216(3) 1 calc R U P A 2
C9B C 0.3610(14) 0.428(4) 0.4155(17) 0.0377(10) Uani 0.216(3) 1 d D U P A 2
H9B H 0.3971 0.4830 0.3729 0.045 Uiso 0.216(3) 1 calc R U P A 2
C10B C 0.3996(18) 0.316(4) 0.4939(17) 0.0359(10) Uani 0.216(3) 1 d D U P A 2
H10B H 0.4688 0.2774 0.5121 0.043 Uiso 0.216(3) 1 calc R U P A 2
S1B S 0.3116(9) 0.250(2) 0.5563(10) 0.0413(12) Uani 0.216(3) 1 d D U P A 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
C1 C2 1.3900 . ?
C1 C6 1.3900 . ?
C1 C11 1.529(2) . ?
C2 C3 1.3900 . ?
C3 C4 1.3900 . ?
C4 C5 1.3900 . ?
C5 C6 1.3900 . ?
C11 C18 1.409(3) . ?
C11 C12 1.429(3) . ?
C12 C13 1.423(3) . ?
C12 C12 1.467(4) 3_566 ?
C13 C14 1.408(3) . ?
C13 C7B 1.478(16) . ?
C13 C7A 1.498(5) . ?
C14 C18 1.431(3) 3_566 ?
C14 C15 1.439(3) . ?
C15 C16 1.352(4) . ?
C16 C17 1.411(4) . ?
C17 C19 1.361(4) 3_566 ?
C18 C14 1.431(3) 3_566 ?
C18 C19 1.437(3) . ?
C19 C17 1.361(4) 3_566 ?
S1A C7A 1.710(8) . ?
S1A C10A 1.733(4) . ?
C7A C8A 1.365(12) . ?
C8A C9A 1.424(13) . ?
C9A C10A 1.378(6) . ?
C7B C8B 1.35(2) . ?
C7B S1B 1.69(2) . ?
C8B C9B 1.44(2) . ?
C9B C10B 1.368(16) . ?
C10B S1B 1.718(17) . ?

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 120.0 . . ?
C2 C1 C11 121.32(13) . . ?
C6 C1 C11 118.32(13) . . ?
C3 C2 C1 120.0 . . ?
C2 C3 C4 120.0 . . ?
C5 C4 C3 120.0 . . ?
C4 C5 C6 120.0 . . ?
C5 C6 C1 120.0 . . ?
C18 C11 C12 120.7(2) . . ?
C18 C11 C1 115.37(19) . . ?
C12 C11 C1 123.6(2) . . ?
C13 C12 C11 122.2(2) . . ?
C13 C12 C12 119.1(3) . 3_566 ?
C11 C12 C12 118.8(3) . 3_566 ?
C14 C13 C12 120.6(2) . . ?
C14 C13 C7B 121(2) . . ?
C12 C13 C7B 118(2) . . ?
C14 C13 C7A 114.0(6) . . ?
C12 C13 C7A 125.0(5) . . ?
C13 C14 C18 120.3(2) . 3_566 ?
C13 C14 C15 121.8(2) . . ?
C18 C14 C15 117.9(2) 3_566 . ?
C16 C15 C14 121.7(2) . . ?
C15 C16 C17 120.5(2) . . ?
C19 C17 C16 120.2(2) 3_566 . ?
C11 C18 C14 120.0(2) . 3_566 ?
C11 C18 C19 121.7(2) . . ?
C14 C18 C19 118.2(2) 3_566 . ?
C17 C19 C18 121.4(2) 3_566 . ?
C7A S1A C10A 92.0(3) . . ?
C8A C7A C13 129.2(9) . . ?
C8A C7A S1A 111.6(7) . . ?
C13 C7A S1A 119.1(5) . . ?
C7A C8A C9A 113.5(11) . . ?
C10A C9A C8A 111.6(7) . . ?
C9A C10A S1A 111.4(5) . . ?
C8B C7B C13 122(2) . . ?
C8B C7B S1B 107.6(16) . . ?
C13 C7B S1B 124.8(19) . . ?
C7B C8B C9B 119(2) . . ?
C10B C9B C8B 106(2) . . ?
C9B C10B S1B 114(2) . . ?
C7B S1B C10B 93.0(14) . . ?

_refine_diff_density_max         0.481
_refine_diff_density_min         -0.357
_refine_diff_density_rms         0.062

_shelxl_version_number           2013-3
_database_code_depnum_ccdc_archive 'CCDC 970524'
#######################################################################
#
#                 Cambridge Crystallographic Data Centre
#                                CCDC 
# 
#######################################################################
# 
#  This CIF contains data from an original supplementary publication
#  deposited with the CCDC, and may include chemical, crystal,
#  experimental, refinement, atomic coordinates,
#  anisotropic displacement parameters and molecular geometry data,
#  as required by the journal to which it was submitted.
#
#  This CIF is provided on the understanding that it is used for bona
#  fide research purposes only. It may contain copyright material
#  of the CCDC or of third parties, and may not be copied or further
#  disseminated in any form, whether machine-readable or not,
#  except for the purpose of generating routine backup copies
#  on your local computer system.
# 
#  For further information on the CCDC, data deposition and
#  data retrieval see:
#                         www.ccdc.cam.ac.uk
#
#  Bona fide researchers may freely download Mercury and enCIFer
#  from this site to visualise CIF-encoded structures and 
#  to carry out CIF format checking respectively.
#
data_Compound_E

_audit_creation_method           
'SHELXL-2012 & Rigaku CrystalClear-SM Expert 2.0 r4'

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'
S S 0.1246 0.1234 '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'

_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                   10.5166(2)
_cell_length_b                   17.9901(4)
_cell_length_c                   15.6600(4)
_cell_angle_alpha                90
_cell_angle_beta                 105.5490(10)
_cell_angle_gamma                90
_cell_volume                     2854.35(11)
_cell_formula_units_Z            4
_cell_measurement_temperature    253(2)
_cell_measurement_reflns_used    13126
_cell_measurement_theta_min      1.8
_cell_measurement_theta_max      27.5

_exptl_crystal_description       Prism
_exptl_crystal_colour            Red
_exptl_crystal_size_max          0.80
_exptl_crystal_size_mid          0.50
_exptl_crystal_size_min          0.24
_chemical_formula_weight         581.19
_chemical_formula_analytical     ?
_chemical_formula_sum            'C38 H25 Cl1 S2 '
_exptl_absorpt_coefficient_mu    0.31
_exptl_absorpt_correction_type   Numerical
_exptl_absorpt_correction_T_max  0.903
_exptl_absorpt_correction_T_min  0.851
_exptl_crystal_F_000             1208
_exptl_absorpt_process_details   
;
'CrystalClear-SM Expert 2.0 r4 (Rigaku, 2009)'
;

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      253(2)
_diffrn_source_power             1.8
_diffrn_source_voltage           50.0
_diffrn_source_current           35.0
_diffrn_radiation_wavelength     0.71075
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  'Graphite Monochromator'
_diffrn_measurement_device       'Crystal Goniometer'
_diffrn_measurement_device_type  'Rigaku RAXIS II'
_diffrn_measurement_specimen_support Fiber
_diffrn_detector                 'Curved image plate'
_diffrn_measurement_method       'profile data from ω-scans'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_reflns_number            16313
_diffrn_reflns_av_unetI/netI     0.0390
_diffrn_reflns_av_R_equivalents  0.0282
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_k_min       -22
_diffrn_reflns_limit_k_max       23
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_theta_min         2.264
_diffrn_reflns_theta_max         27.495
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.993
_diffrn_measured_fraction_theta_full 0.991
_diffrn_reflns_Laue_measured_fraction_max 0.993
_diffrn_reflns_Laue_measured_fraction_full 0.991
_diffrn_reflns_point_group_measured_fraction_max 0.993
_diffrn_reflns_point_group_measured_fraction_full 0.991
_reflns_number_total             6500
_reflns_number_gt                5783
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .
_computing_data_collection       
;
CrystalClear-SM Expert 2.0 r4 (Rigaku, 2009)
;
_computing_cell_refinement       
;
CrystalClear-SM Expert 2.0 r4 (Rigaku, 2009)
;
_computing_data_reduction        
;
CrystalClear-SM Expert 2.0 r4 (Rigaku, 2009)
;
_computing_structure_solution    'SHELXS-2013 (Sheldrick, 2013)'
_computing_structure_refinement  'SHELXL-2013 (Sheldrick, 2013)'
_computing_molecular_graphics    ?
_computing_publication_material  ?

_refine_special_details          
;
'Refinement of F² against ALL reflections.  The weighted R-factor wR and
 goodness of fit S are based on F², conventional R-factors R are based
 on F, with F set to zero for negative F². The threshold expression of
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is
 not relevant to the choice of reflections for refinement.  R-factors based
 on F² are statistically about twice as large as those based on F, and R-
 factors based on ALL data will be even larger.'
;
_diffrn_measurement_details      
;
scan:
	Number of images: 44
	           Slice: 24.0000 - 156.0000
	     Image width: 3.0000
	        Exp time: 180.0000
	   Rotation axis: Omega
	           Omega: 0.0000
	             Chi: 0.0000
	             Phi: 180.0000
	             XTD: 127.4000
	          2theta: -0.0434

;
_diffrn_orient_matrix_UB_11      0.064552
_diffrn_orient_matrix_UB_12      0.012905
_diffrn_orient_matrix_UB_13      -0.073541
_diffrn_orient_matrix_UB_21      -0.036888
_diffrn_orient_matrix_UB_22      0.031793
_diffrn_orient_matrix_UB_23      -0.026800
_diffrn_orient_matrix_UB_31      0.034809
_diffrn_orient_matrix_UB_32      0.054034
_diffrn_orient_matrix_UB_33      0.016189
_diffrn_orient_matrix_type       d*Trek

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0434P)²+1.4729P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         6499
_refine_ls_number_parameters     386
_refine_ls_number_restraints     407
_refine_ls_R_factor_all          0.0530
_refine_ls_R_factor_gt           0.0459
_refine_ls_wR_factor_ref         0.1131
_refine_ls_wR_factor_gt          0.1080
_refine_ls_goodness_of_fit_ref   1.014
_refine_ls_restrained_S_all      0.994
_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
C1 C 0.26123(17) 0.03236(10) 0.38676(12) 0.0339(4) Uani 1 1 d . U . . .
C2 C 0.22629(19) -0.00248(10) 0.45666(14) 0.0410(4) Uani 1 1 d . U . . .
H2 H 0.2793 0.0033 0.5142 0.049 Uiso 1 1 calc R U . . .
C3 C 0.1132(2) -0.04574(12) 0.44121(17) 0.0528(5) Uani 1 1 d . U . . .
H3 H 0.0902 -0.0683 0.4884 0.063 Uiso 1 1 calc R U . . .
C4 C 0.0347(2) -0.05527(13) 0.35573(19) 0.0597(6) Uani 1 1 d . U . . .
H4 H -0.0419 -0.0836 0.3455 0.072 Uiso 1 1 calc R U . . .
C5 C 0.0698(2) -0.02292(13) 0.28576(17) 0.0560(6) Uani 1 1 d . U . . .
H5 H 0.0177 -0.0303 0.2283 0.067 Uiso 1 1 calc R U . . .
C6 C 0.18260(19) 0.02073(11) 0.30031(14) 0.0436(4) Uani 1 1 d . U . . .
H6 H 0.2059 0.0422 0.2526 0.052 Uiso 1 1 calc R U . . .
C7 C 0.64539(16) 0.27376(9) 0.60038(11) 0.0305(3) Uani 1 1 d . U . . .
C8 C 0.70572(18) 0.34258(10) 0.59972(12) 0.0364(4) Uani 1 1 d . U . . .
H8 H 0.6587 0.3813 0.5662 0.044 Uiso 1 1 calc R U . . .
C9 C 0.83572(19) 0.35401(12) 0.64878(14) 0.0451(5) Uani 1 1 d . U . . .
H9 H 0.8751 0.4000 0.6465 0.054 Uiso 1 1 calc R U . . .
C10 C 0.90672(18) 0.29849(13) 0.70040(13) 0.0463(5) Uani 1 1 d . U . . .
H10 H 0.9926 0.3071 0.7343 0.056 Uiso 1 1 calc R U . . .
C11 C 0.84924(19) 0.22993(13) 0.70137(13) 0.0453(5) Uani 1 1 d . U . . .
H11 H 0.8969 0.1918 0.7357 0.054 Uiso 1 1 calc R U . . .
C12 C 0.72076(17) 0.21725(11) 0.65155(12) 0.0379(4) Uani 1 1 d . U . . .
H12 H 0.6839 0.1703 0.6521 0.045 Uiso 1 1 calc R U . . .
C13 C 0.42044(16) 0.32711(9) 0.50939(12) 0.0329(4) Uani 1 1 d . U . . .
C14 C 0.4185(2) 0.38961(11) 0.56206(15) 0.0459(5) Uani 1 1 d . U . . .
H14 H 0.4719 0.3909 0.6200 0.055 Uiso 1 1 calc R U . . .
C15 C 0.3381(3) 0.44959(13) 0.5290(2) 0.0691(7) Uani 1 1 d . U . . .
H15 H 0.3386 0.4910 0.5647 0.083 Uiso 1 1 calc R U . . .
C16 C 0.2576(3) 0.44872(15) 0.4442(2) 0.0790(8) Uani 1 1 d . U . . .
H16 H 0.2024 0.4888 0.4230 0.095 Uiso 1 1 calc R U . . .
C17 C 0.2586(2) 0.38818(14) 0.39029(19) 0.0641(6) Uani 1 1 d . U . . .
H17 H 0.2052 0.3877 0.3324 0.077 Uiso 1 1 calc R U . . .
C18 C 0.33969(18) 0.32794(11) 0.42281(14) 0.0420(4) Uani 1 1 d . U . . .
H18 H 0.3401 0.2874 0.3861 0.050 Uiso 1 1 calc R U . . .
C19 C 0.58661(15) 0.18849(9) 0.42938(10) 0.0283(3) Uani 1 1 d . U . . .
C20 C 0.58605(16) 0.12262(9) 0.37635(11) 0.0300(3) Uani 1 1 d . U . . .
C21 C 0.68684(18) 0.10832(10) 0.33328(12) 0.0366(4) Uani 1 1 d . U . . .
H21 H 0.7515 0.1440 0.3351 0.044 Uiso 1 1 calc R U . . .
C22 C 0.6899(2) 0.04281(11) 0.28924(14) 0.0448(5) Uani 1 1 d . U . . .
H22 H 0.7573 0.0343 0.2623 0.054 Uiso 1 1 calc R U . . .
C23 C 0.5930(2) -0.01123(11) 0.28439(14) 0.0466(5) Uani 1 1 d . U . . .
H23 H 0.5975 -0.0561 0.2558 0.056 Uiso 1 1 calc R U . . .
C24 C 0.49122(19) 0.00177(10) 0.32162(13) 0.0404(4) Uani 1 1 d . U . . .
H24 H 0.4258 -0.0340 0.3168 0.049 Uiso 1 1 calc R U . . .
C25 C 0.48419(17) 0.06918(9) 0.36749(11) 0.0316(3) Uani 1 1 d . U . . .
C26 C 0.37598(16) 0.08430(9) 0.40432(11) 0.0302(3) Uani 1 1 d . U . . .
C27 C 0.38004(15) 0.14713(9) 0.45651(11) 0.0282(3) Uani 1 1 d . U . . .
C28 C 0.26802(15) 0.16879(9) 0.49162(11) 0.0306(3) Uani 1 1 d . U . . .
C29 C 0.29192(16) 0.20315(9) 0.56940(11) 0.0313(3) Uani 1 1 d . U . . .
C30 C 0.43218(16) 0.22163(9) 0.61712(11) 0.0304(3) Uani 1 1 d . U . . .
H30 H 0.4783 0.1753 0.6391 0.036 Uiso 1 1 calc R U . . .
C31 C 0.50067(15) 0.25764(9) 0.54842(11) 0.0275(3) Uani 1 1 d . U . . .
C32 C 0.49279(15) 0.19670(9) 0.47638(10) 0.0265(3) Uani 1 1 d . U . . .
C33 C 0.42519(19) 0.26824(11) 0.69557(12) 0.0399(4) Uani 1 1 d . U . . .
H33 H 0.4999 0.2880 0.7350 0.048 Uiso 1 1 calc R U . . .
C34 C 0.3046(2) 0.27904(12) 0.70427(13) 0.0451(5) Uani 1 1 d . U . . .
H34 H 0.2889 0.3057 0.7513 0.054 Uiso 1 1 calc R U . . .
S2 S 0.17624(5) 0.23924(3) 0.62045(3) 0.04500(14) Uani 1 1 d . U . . .
C35A C 0.6880(7) 0.2486(6) 0.4274(12) 0.0301(6) Uani 0.751(3) 1 d D U P A 1
C36A C 0.8220(9) 0.2464(7) 0.4625(9) 0.0412(9) Uani 0.751(3) 1 d D U P A 1
H36A H 0.8666 0.2064 0.4945 0.049 Uiso 0.751(3) 1 calc R U P A 1
C37A C 0.8859(6) 0.3128(3) 0.4444(5) 0.0414(8) Uani 0.751(3) 1 d D U P A 1
H37A H 0.9764 0.3210 0.4633 0.050 Uiso 0.751(3) 1 calc R U P A 1
C38A C 0.7971(3) 0.3625(2) 0.3959(3) 0.0418(8) Uani 0.751(3) 1 d D U P A 1
H38A H 0.8203 0.4086 0.3778 0.050 Uiso 0.751(3) 1 calc R U P A 1
S1A S 0.63749(8) 0.32996(4) 0.37204(6) 0.0384(2) Uani 0.751(3) 1 d D U P A 1
C35B C 0.677(2) 0.244(2) 0.428(4) 0.0301(6) Uani 0.249(3) 1 d D U P A 2
S1B S 0.8454(6) 0.2389(5) 0.4690(7) 0.0412(9) Uani 0.249(3) 1 d D U P A 2
C38B C 0.870(2) 0.3251(11) 0.4297(17) 0.0414(8) Uani 0.249(3) 1 d D U P A 2
H38B H 0.9521 0.3472 0.4387 0.050 Uiso 0.249(3) 1 calc R U P A 2
C37B C 0.7558(11) 0.3576(9) 0.3840(11) 0.0418(8) Uani 0.249(3) 1 d D U P A 2
H37B H 0.7488 0.4040 0.3571 0.050 Uiso 0.249(3) 1 calc R U P A 2
C36B C 0.6496(13) 0.3099(6) 0.3837(9) 0.0384(2) Uani 0.249(3) 1 d D U P A 2
H36B H 0.5634 0.3228 0.3542 0.046 Uiso 0.249(3) 1 calc R U P A 2
Cl Cl 0.10641(4) 0.16318(3) 0.42514(3) 0.04508(13) Uani 1 1 d . 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
C1 C2 1.393(3) . ?
C1 C6 1.400(3) . ?
C1 C26 1.492(2) . ?
C2 C3 1.387(3) . ?
C3 C4 1.382(4) . ?
C4 C5 1.376(4) . ?
C5 C6 1.389(3) . ?
C7 C8 1.392(2) . ?
C7 C12 1.401(3) . ?
C7 C31 1.549(2) . ?
C8 C9 1.392(3) . ?
C9 C10 1.373(3) . ?
C10 C11 1.376(3) . ?
C11 C12 1.386(3) . ?
C13 C18 1.394(3) . ?
C13 C14 1.398(3) . ?
C13 C31 1.540(2) . ?
C14 C15 1.383(3) . ?
C15 C16 1.370(4) . ?
C16 C17 1.380(4) . ?
C17 C18 1.389(3) . ?
C19 C35B 1.38(2) . ?
C19 C32 1.388(2) . ?
C19 C20 1.446(2) . ?
C19 C35A 1.525(6) . ?
C20 C25 1.418(2) . ?
C20 C21 1.424(2) . ?
C21 C22 1.370(3) . ?
C22 C23 1.396(3) . ?
C23 C24 1.369(3) . ?
C24 C25 1.422(2) . ?
C25 C26 1.433(2) . ?
C26 C27 1.389(2) . ?
C27 C32 1.449(2) . ?
C27 C28 1.480(2) . ?
C28 C29 1.328(2) . ?
C28 Cl 1.7417(17) . ?
C29 C30 1.501(2) . ?
C29 S2 1.7498(16) . ?
C30 C33 1.505(2) . ?
C30 C31 1.585(2) . ?
C31 C32 1.559(2) . ?
C33 C34 1.325(3) . ?
C34 S2 1.763(2) . ?
C35A C36A 1.369(12) . ?
C35A S1A 1.711(9) . ?
C36A C37A 1.435(12) . ?
C37A C38A 1.366(5) . ?
C38A S1A 1.722(3) . ?
C35B C36B 1.37(2) . ?
C35B S1B 1.71(2) . ?
S1B C38B 1.712(16) . ?
C38B C37B 1.350(14) . ?
C37B C36B 1.407(14) . ?

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 118.73(17) . . ?
C2 C1 C26 120.49(16) . . ?
C6 C1 C26 120.70(17) . . ?
C3 C2 C1 120.6(2) . . ?
C4 C3 C2 120.0(2) . . ?
C5 C4 C3 120.0(2) . . ?
C4 C5 C6 120.5(2) . . ?
C5 C6 C1 120.0(2) . . ?
C8 C7 C12 117.41(16) . . ?
C8 C7 C31 123.24(15) . . ?
C12 C7 C31 119.35(15) . . ?
C9 C8 C7 120.61(18) . . ?
C10 C9 C8 121.07(19) . . ?
C9 C10 C11 119.18(18) . . ?
C10 C11 C12 120.42(19) . . ?
C11 C12 C7 121.27(18) . . ?
C18 C13 C14 117.65(17) . . ?
C18 C13 C31 121.40(16) . . ?
C14 C13 C31 120.78(16) . . ?
C15 C14 C13 120.7(2) . . ?
C16 C15 C14 120.7(2) . . ?
C15 C16 C17 119.9(2) . . ?
C16 C17 C18 119.8(2) . . ?
C17 C18 C13 121.3(2) . . ?
C35B C19 C32 121(3) . . ?
C35B C19 C20 119(3) . . ?
C32 C19 C20 119.85(15) . . ?
C32 C19 C35A 122.4(8) . . ?
C20 C19 C35A 117.7(8) . . ?
C25 C20 C21 118.02(15) . . ?
C25 C20 C19 119.89(14) . . ?
C21 C20 C19 122.08(15) . . ?
C22 C21 C20 120.97(17) . . ?
C21 C22 C23 120.75(17) . . ?
C24 C23 C22 120.03(18) . . ?
C23 C24 C25 120.90(18) . . ?
C20 C25 C24 119.18(15) . . ?
C20 C25 C26 119.50(15) . . ?
C24 C25 C26 121.32(16) . . ?
C27 C26 C25 119.27(15) . . ?
C27 C26 C1 120.92(14) . . ?
C25 C26 C1 119.81(15) . . ?
C26 C27 C32 121.43(14) . . ?
C26 C27 C28 122.07(15) . . ?
C32 C27 C28 116.44(14) . . ?
C29 C28 C27 119.30(15) . . ?
C29 C28 Cl 119.30(13) . . ?
C27 C28 Cl 120.61(12) . . ?
C28 C29 C30 118.59(14) . . ?
C28 C29 S2 127.42(13) . . ?
C30 C29 S2 113.65(12) . . ?
C29 C30 C33 105.85(14) . . ?
C29 C30 C31 108.50(13) . . ?
C33 C30 C31 117.18(14) . . ?
C13 C31 C7 114.41(13) . . ?
C13 C31 C32 111.49(13) . . ?
C7 C31 C32 111.47(12) . . ?
C13 C31 C30 107.51(13) . . ?
C7 C31 C30 106.34(13) . . ?
C32 C31 C30 104.95(12) . . ?
C19 C32 C27 118.53(14) . . ?
C19 C32 C31 123.44(14) . . ?
C27 C32 C31 118.02(13) . . ?
C34 C33 C30 115.02(17) . . ?
C33 C34 S2 115.26(15) . . ?
C29 S2 C34 90.19(9) . . ?
C36A C35A C19 128.4(8) . . ?
C36A C35A S1A 112.0(6) . . ?
C19 C35A S1A 119.6(5) . . ?
C35A C36A C37A 112.5(9) . . ?
C38A C37A C36A 111.6(6) . . ?
C37A C38A S1A 112.3(4) . . ?
C35A S1A C38A 91.6(3) . . ?
C36B C35B C19 125.3(19) . . ?
C36B C35B S1B 106.8(13) . . ?
C19 C35B S1B 127.4(19) . . ?
C38B S1B C35B 93.4(12) . . ?
C37B C38B S1B 112.7(15) . . ?
C38B C37B C36B 109.2(15) . . ?
C35B C36B C37B 117.9(14) . . ?

_refine_diff_density_max         0.254
_refine_diff_density_min         -0.310
_refine_diff_density_rms         0.041

_shelxl_version_number           2013-3
_database_code_depnum_ccdc_archive 'CCDC 970525'
#######################################################################
#
#                 Cambridge Crystallographic Data Centre
#                                CCDC 
# 
#######################################################################
# 
#  This CIF contains data from an original supplementary publication
#  deposited with the CCDC, and may include chemical, crystal,
#  experimental, refinement, atomic coordinates,
#  anisotropic displacement parameters and molecular geometry data,
#  as required by the journal to which it was submitted.
#
#  This CIF is provided on the understanding that it is used for bona
#  fide research purposes only. It may contain copyright material
#  of the CCDC or of third parties, and may not be copied or further
#  disseminated in any form, whether machine-readable or not,
#  except for the purpose of generating routine backup copies
#  on your local computer system.
# 
#  For further information on the CCDC, data deposition and
#  data retrieval see:
#                         www.ccdc.cam.ac.uk
#
#  Bona fide researchers may freely download Mercury and enCIFer
#  from this site to visualise CIF-encoded structures and 
#  to carry out CIF format checking respectively.
#
data_Compound_H

_audit_creation_method           
'SHELXL-2013 & Rigaku CrystalClear-SM Expert 2.0 r15'

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_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, -z'

_cell_length_a                   9.4762(2)
_cell_length_b                   11.5861(4)
_cell_length_c                   13.4449(5)
_cell_angle_alpha                82.999(9)
_cell_angle_beta                 79.945(8)
_cell_angle_gamma                77.745(8)
_cell_volume                     1414.82(10)
_cell_formula_units_Z            2
_cell_measurement_temperature    203
_cell_measurement_reflns_used    10627
_cell_measurement_theta_min      3.1
_cell_measurement_theta_max      26.5
_symmetry_cell_setting           triclinic
_symmetry_space_group_name_H-M   'P -1'
_symmetry_Int_Tables_number      2

_exptl_crystal_description       Prism
_exptl_crystal_colour            Colorless
_exptl_crystal_size_max          0.25
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.10
_chemical_formula_weight         581.19
_chemical_formula_analytical     ?
_chemical_formula_sum            'C38 H25 Cl1 S2 '
_exptl_absorpt_coefficient_mu    0.31
_exptl_absorpt_correction_type   Numerical
_exptl_absorpt_correction_T_max  0.975
_exptl_absorpt_correction_T_min  0.941
_exptl_crystal_F_000             604
_exptl_absorpt_process_details   
;
'CrystalClear-SM Expert 2.0 r4 (Rigaku, 2009)'
;

_diffrn_ambient_temperature      203(2)
_diffrn_source_power             1.8
_diffrn_source_voltage           50.0
_diffrn_source_current           35.0
_diffrn_radiation_wavelength     0.71075
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  'Graphite Monochromator'
_diffrn_measurement_device       'Crystal Goniometer'
_diffrn_measurement_device_type  'Rigaku RAXIS II'
_diffrn_measurement_specimen_support Fiber
_diffrn_detector                 'Curved image plate'
_diffrn_measurement_method       'profile data from ω-scans'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_reflns_number            22554
_diffrn_reflns_av_unetI/netI     0.1186
_diffrn_reflns_av_R_equivalents  0.1430
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_theta_min         3.090
_diffrn_reflns_theta_max         26.023
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measured_fraction_theta_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_point_group_measured_fraction_full 0.997
_reflns_number_total             5569
_reflns_number_gt                3092
_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.
;
_diffrn_measurement_details      
;
scan:
        Number of images: 50
                   Slice: 20.0000 - 170.0000
             Image width: 3.0000
                Exp time: 240.0000
           Rotation axis: Omega
                   Omega: 0.0000
                     Chi: 54.0000
                     Phi: 90.0000
                     XTD: 127.4000
                  2theta: -0.0319
scan:
        Number of images: 44
                   Slice: 20.0000 - 152.0000
             Image width: 3.0000
                Exp time: 240.0000
           Rotation axis: Omega
                   Omega: 0.0000
                     Chi: 30.0000
                     Phi: 270.0000
                     XTD: 127.4000
                  2theta: -0.0319
scan:
        Number of images: 40
                   Slice: 50.0000 - 170.0000
             Image width: 3.0000
                Exp time: 240.0000
           Rotation axis: Omega
                   Omega: 0.0000
                     Chi: 0.0000
                     Phi: 0.0000
                     XTD: 127.4000
                  2theta: -0.0319

;
_diffrn_orient_matrix_UB_11      0.087760
_diffrn_orient_matrix_UB_12      -0.035072
_diffrn_orient_matrix_UB_13      -0.047805
_diffrn_orient_matrix_UB_21      0.050927
_diffrn_orient_matrix_UB_22      -0.036163
_diffrn_orient_matrix_UB_23      0.059047
_diffrn_orient_matrix_UB_31      -0.041133
_diffrn_orient_matrix_UB_32      -0.073251
_diffrn_orient_matrix_UB_33      0.001969
_diffrn_orient_matrix_type       FS_PROCESS
_computing_data_collection       
;
CrystalClear-SM Expert 2.0 r4 (Rigaku, 2009)
;
_computing_cell_refinement       
;
CrystalClear-SM Expert 2.0 r4 (Rigaku, 2009)
;
_computing_data_reduction        
;
CrystalClear-SM Expert 2.0 r4 (Rigaku, 2009)
;
_computing_structure_solution    'SHELXS-2013 (Sheldrick, 2013)'
_computing_structure_refinement  'SHELXL-2013 (Sheldrick, 2013)'
_computing_molecular_graphics    ?
_computing_publication_material  ?

_refine_special_details          
;
'Refinement of F² against ALL reflections.  The weighted R-factor wR and
 goodness of fit S are based on F², conventional R-factors R are based
 on F, with F set to zero for negative F². The threshold expression of
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is
 not relevant to the choice of reflections for refinement.  R-factors based
 on F² are statistically about twice as large as those based on F, and R-
 factors based on ALL data will be even larger.'
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0590P)²] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         5747
_refine_ls_number_parameters     386
_refine_ls_number_restraints     408
_refine_ls_R_factor_all          0.1424
_refine_ls_R_factor_gt           0.0737
_refine_ls_wR_factor_ref         0.1773
_refine_ls_wR_factor_gt          0.1455
_refine_ls_goodness_of_fit_ref   1.016
_refine_ls_restrained_S_all      0.990
_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
Cl1 Cl 0.07716(10) 0.12323(9) 0.40447(7) 0.0581(3) Uani 1 1 d . U . . .
S2 S 0.27117(11) -0.14132(9) 0.45391(7) 0.0574(3) Uani 1 1 d . U . . .
C1 C 0.2510(4) 0.3799(3) 0.2976(3) 0.0439(9) Uani 1 1 d . U . . .
C2 C 0.1457(4) 0.4791(3) 0.2760(3) 0.0520(10) Uani 1 1 d . U . . .
H2 H 0.1066 0.4867 0.2162 0.062 Uiso 1 1 calc R U . . .
C3 C 0.0982(4) 0.5674(4) 0.3429(3) 0.0632(12) Uani 1 1 d . U . . .
H3 H 0.0287 0.6337 0.3270 0.076 Uiso 1 1 calc R U . . .
C4 C 0.1538(5) 0.5566(4) 0.4323(3) 0.0654(12) Uani 1 1 d . U . . .
H4 H 0.1225 0.6158 0.4767 0.078 Uiso 1 1 calc R U . . .
C5 C 0.2573(4) 0.4565(4) 0.4558(3) 0.0636(12) Uani 1 1 d . U . . .
H5 H 0.2954 0.4487 0.5160 0.076 Uiso 1 1 calc R U . . .
C6 C 0.3033(4) 0.3687(4) 0.3897(3) 0.0549(10) Uani 1 1 d . U . . .
H6 H 0.3702 0.3012 0.4069 0.066 Uiso 1 1 calc R U . . .
C7 C 0.2190(4) 0.2958(3) 0.1399(3) 0.0422(9) Uani 1 1 d . U . . .
C8 C 0.2367(4) 0.3826(3) 0.0588(3) 0.0469(9) Uani 1 1 d . U . . .
H8 H 0.3043 0.4305 0.0580 0.056 Uiso 1 1 calc R U . . .
C9 C 0.1573(4) 0.3987(4) -0.0190(3) 0.0548(10) Uani 1 1 d . U . . .
H9 H 0.1694 0.4580 -0.0712 0.066 Uiso 1 1 calc R U . . .
C10 C 0.0579(4) 0.3259(4) -0.0201(3) 0.0617(11) Uani 1 1 d . U . . .
H10 H 0.0061 0.3344 -0.0741 0.074 Uiso 1 1 calc R U . . .
C11 C 0.0370(4) 0.2414(4) 0.0595(3) 0.0604(11) Uani 1 1 d . U . . .
H11 H -0.0324 0.1951 0.0605 0.073 Uiso 1 1 calc R U . . .
C12 C 0.1176(4) 0.2248(4) 0.1376(3) 0.0513(10) Uani 1 1 d . U . . .
H12 H 0.1045 0.1655 0.1896 0.062 Uiso 1 1 calc R U . . .
C13 C 0.5422(4) 0.2361(3) 0.0725(2) 0.0385(8) Uani 1 1 d . U . . .
C14 C 0.6423(4) 0.2989(3) 0.0147(3) 0.0437(9) Uani 1 1 d . U . . .
H14 H 0.6809 0.3506 0.0451 0.052 Uiso 1 1 calc R U . . .
C15 C 0.6851(4) 0.2855(3) -0.0878(3) 0.0497(10) Uani 1 1 d . U . . .
H15 H 0.7526 0.3280 -0.1253 0.060 Uiso 1 1 calc R U . . .
C16 C 0.6292(4) 0.2103(3) -0.1348(3) 0.0516(10) Uani 1 1 d . U . . .
H16 H 0.6583 0.2022 -0.2037 0.062 Uiso 1 1 calc R U . . .
C17 C 0.5303(4) 0.1473(3) -0.0795(3) 0.0491(10) Uani 1 1 d . U . . .
H17 H 0.4913 0.0968 -0.1111 0.059 Uiso 1 1 calc R U . . .
C18 C 0.4884(4) 0.1587(3) 0.0235(3) 0.0462(9) Uani 1 1 d . U . . .
H18 H 0.4232 0.1140 0.0607 0.055 Uiso 1 1 calc R U . . .
C19 C 0.5756(4) 0.3272(3) 0.2267(2) 0.0414(9) Uani 1 1 d . U . . .
C20 C 0.6912(4) 0.2809(3) 0.2780(3) 0.0486(10) Uani 1 1 d . U . . .
H20 H 0.7165 0.1994 0.2931 0.058 Uiso 1 1 calc R U . . .
C21 C 0.7710(4) 0.3563(4) 0.3077(3) 0.0543(10) Uani 1 1 d . U . . .
H21 H 0.8502 0.3245 0.3414 0.065 Uiso 1 1 calc R U . . .
C22 C 0.7324(4) 0.4777(4) 0.2870(3) 0.0542(10) Uani 1 1 d . U . . .
H22 H 0.7856 0.5273 0.3070 0.065 Uiso 1 1 calc R U . . .
C23 C 0.6159(4) 0.5254(4) 0.2372(3) 0.0521(10) Uani 1 1 d . U . . .
H23 H 0.5891 0.6071 0.2242 0.063 Uiso 1 1 calc R U . . .
C24 C 0.5381(4) 0.4508(3) 0.2062(3) 0.0469(9) Uani 1 1 d . U . . .
H24 H 0.4601 0.4831 0.1715 0.056 Uiso 1 1 calc R U . . .
C25 C 0.3077(4) 0.2816(3) 0.2256(2) 0.0412(8) Uani 1 1 d . U . . .
C26 C 0.4920(4) 0.2479(3) 0.1864(2) 0.0402(8) Uani 1 1 d . U . . .
C27 C 0.4816(4) 0.1287(3) 0.2489(2) 0.0396(8) Uani 1 1 d . U . . .
C28 C 0.5674(4) 0.0194(3) 0.2758(2) 0.0407(8) Uani 1 1 d . U . . .
C29 C 0.4911(4) -0.0624(3) 0.3407(2) 0.0432(9) Uani 1 1 d . U . . .
C30 C 0.3394(4) -0.0273(3) 0.3774(2) 0.0415(9) Uani 1 1 d . U . . .
C31 C 0.2594(4) 0.0846(3) 0.3508(2) 0.0439(9) Uani 1 1 d . U . . .
C32 C 0.3320(4) 0.1586(3) 0.2824(2) 0.0402(8) Uani 1 1 d . U . . .
C33 C 0.5439(4) -0.1832(3) 0.3754(3) 0.0493(10) Uani 1 1 d . U . . .
H33 H 0.6403 -0.2221 0.3588 0.059 Uiso 1 1 calc R U . . .
C34 C 0.4401(4) -0.2353(4) 0.4347(3) 0.0561(10) Uani 1 1 d . U . . .
H34 H 0.4576 -0.3137 0.4623 0.067 Uiso 1 1 calc R U . . .
C35A C 0.7287(8) -0.0148(12) 0.2448(7) 0.0431(12) Uani 0.804(3) 1 d D U P A 1
C36A C 0.8334(9) -0.0619(8) 0.3047(5) 0.0531(18) Uani 0.804(3) 1 d D U P A 1
H36A H 0.8106 -0.0730 0.3749 0.064 Uiso 0.804(3) 1 calc R U P A 1
C37A C 0.9770(10) -0.0925(9) 0.2544(7) 0.0559(18) Uani 0.804(3) 1 d D U P A 1
H37A H 1.0590 -0.1240 0.2854 0.067 Uiso 0.804(3) 1 calc R U P A 1
C38A C 0.9765(8) -0.0685(7) 0.1528(7) 0.0544(19) Uani 0.804(3) 1 d D U P A 1
H38A H 1.0607 -0.0832 0.1053 0.065 Uiso 0.804(3) 1 calc R U P A 1
S1A S 0.8076(2) -0.0091(2) 0.12002(10) 0.0597(6) Uani 0.804(3) 1 d D U P A 1
C35B C 0.721(3) -0.022(5) 0.246(3) 0.0431(12) Uani 0.196(3) 1 d D U P A 2
S1B S 0.8357(11) -0.0721(12) 0.3339(6) 0.0597(6) Uani 0.196(3) 1 d D U P A 2
C37B C 0.983(4) -0.073(4) 0.237(3) 0.0544(19) Uani 0.196(3) 1 d D U P A 2
H37B H 1.0783 -0.0957 0.2521 0.065 Uiso 0.196(3) 1 calc R U P A 2
C38B C 0.960(4) -0.040(4) 0.141(4) 0.0559(18) Uani 0.196(3) 1 d D U P A 2
H38B H 1.0275 -0.0368 0.0819 0.067 Uiso 0.196(3) 1 calc R U P A 2
C36B C 0.808(3) -0.012(3) 0.154(2) 0.0531(18) Uani 0.196(3) 1 d D U P A 2
H36B H 0.7631 0.0149 0.0966 0.064 Uiso 0.196(3) 1 calc R U P A 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
Cl1 C31 1.738(3) . ?
S2 C34 1.732(4) . ?
S2 C30 1.737(3) . ?
C1 C2 1.391(5) . ?
C1 C6 1.394(5) . ?
C1 C25 1.533(5) . ?
C2 C3 1.394(5) . ?
C3 C4 1.376(5) . ?
C4 C5 1.394(6) . ?
C5 C6 1.382(5) . ?
C7 C12 1.398(5) . ?
C7 C8 1.404(5) . ?
C7 C25 1.515(5) . ?
C8 C9 1.365(5) . ?
C9 C10 1.393(5) . ?
C10 C11 1.378(5) . ?
C11 C12 1.375(5) . ?
C13 C14 1.390(4) . ?
C13 C18 1.398(5) . ?
C13 C26 1.536(4) . ?
C14 C15 1.385(5) . ?
C15 C16 1.373(5) . ?
C16 C17 1.372(4) . ?
C17 C18 1.387(5) . ?
C19 C20 1.374(5) . ?
C19 C24 1.404(5) . ?
C19 C26 1.531(4) . ?
C20 C21 1.401(5) . ?
C21 C22 1.383(5) . ?
C22 C23 1.372(5) . ?
C23 C24 1.388(5) . ?
C25 C32 1.524(5) . ?
C25 C26 1.709(4) . ?
C26 C27 1.539(4) . ?
C27 C32 1.392(4) . ?
C27 C28 1.396(5) . ?
C28 C29 1.433(4) . ?
C28 C35B 1.44(3) . ?
C28 C35A 1.493(8) . ?
C29 C30 1.424(5) . ?
C29 C33 1.433(5) . ?
C30 C31 1.396(5) . ?
C31 C32 1.376(4) . ?
C33 C34 1.352(5) . ?
C35A C36A 1.369(10) . ?
C35A S1A 1.713(9) . ?
C36A C37A 1.403(10) . ?
C37A C38A 1.361(6) . ?
C38A S1A 1.713(7) . ?
C35B C36B 1.37(2) . ?
C35B S1B 1.71(2) . ?
S1B C37B 1.734(19) . ?
C37B C38B 1.349(18) . ?
C38B C36B 1.39(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
C34 S2 C30 91.15(18) . . ?
C2 C1 C6 118.2(4) . . ?
C2 C1 C25 122.5(3) . . ?
C6 C1 C25 119.2(3) . . ?
C1 C2 C3 120.8(4) . . ?
C4 C3 C2 120.3(4) . . ?
C3 C4 C5 119.5(4) . . ?
C6 C5 C4 120.1(4) . . ?
C5 C6 C1 121.0(4) . . ?
C12 C7 C8 117.4(3) . . ?
C12 C7 C25 122.4(3) . . ?
C8 C7 C25 120.2(3) . . ?
C9 C8 C7 121.7(4) . . ?
C8 C9 C10 119.8(4) . . ?
C11 C10 C9 119.5(4) . . ?
C12 C11 C10 120.6(4) . . ?
C11 C12 C7 120.9(4) . . ?
C14 C13 C18 117.5(3) . . ?
C14 C13 C26 122.5(3) . . ?
C18 C13 C26 120.0(3) . . ?
C15 C14 C13 120.8(3) . . ?
C16 C15 C14 120.8(3) . . ?
C17 C16 C15 119.6(3) . . ?
C16 C17 C18 120.0(3) . . ?
C17 C18 C13 121.3(3) . . ?
C20 C19 C24 118.8(3) . . ?
C20 C19 C26 121.9(3) . . ?
C24 C19 C26 119.2(3) . . ?
C19 C20 C21 120.2(4) . . ?
C22 C21 C20 120.2(4) . . ?
C23 C22 C21 120.3(4) . . ?
C22 C23 C24 119.6(4) . . ?
C23 C24 C19 120.9(4) . . ?
C7 C25 C32 115.3(3) . . ?
C7 C25 C1 112.1(3) . . ?
C32 C25 C1 112.2(3) . . ?
C7 C25 C26 113.3(3) . . ?
C32 C25 C26 83.9(2) . . ?
C1 C25 C26 117.3(3) . . ?
C19 C26 C13 111.4(3) . . ?
C19 C26 C27 116.0(3) . . ?
C13 C26 C27 113.5(3) . . ?
C19 C26 C25 112.9(3) . . ?
C13 C26 C25 116.5(3) . . ?
C27 C26 C25 84.2(2) . . ?
C32 C27 C28 123.3(3) . . ?
C32 C27 C26 95.2(3) . . ?
C28 C27 C26 141.5(3) . . ?
C27 C28 C29 115.5(3) . . ?
C27 C28 C35B 128.5(19) . . ?
C29 C28 C35B 116(2) . . ?
C27 C28 C35A 125.2(5) . . ?
C29 C28 C35A 119.4(5) . . ?
C30 C29 C33 110.8(3) . . ?
C30 C29 C28 119.9(3) . . ?
C33 C29 C28 129.3(3) . . ?
C31 C30 C29 122.3(3) . . ?
C31 C30 S2 126.2(3) . . ?
C29 C30 S2 111.5(3) . . ?
C32 C31 C30 116.9(3) . . ?
C32 C31 Cl1 123.7(3) . . ?
C30 C31 Cl1 119.4(3) . . ?
C31 C32 C27 121.8(3) . . ?
C31 C32 C25 141.4(3) . . ?
C27 C32 C25 96.7(3) . . ?
C34 C33 C29 113.4(4) . . ?
C33 C34 S2 113.1(3) . . ?
C36A C35A C28 128.3(7) . . ?
C36A C35A S1A 109.6(5) . . ?
C28 C35A S1A 121.9(5) . . ?
C35A C36A C37A 116.3(8) . . ?
C38A C37A C36A 108.7(9) . . ?
C37A C38A S1A 114.3(8) . . ?
C35A S1A C38A 91.1(4) . . ?
C36B C35B C28 131(2) . . ?
C36B C35B S1B 107(2) . . ?
C28 C35B S1B 121(2) . . ?
C35B S1B C37B 89(2) . . ?
C38B C37B S1B 120(4) . . ?
C37B C38B C36B 101(4) . . ?
C35B C36B C38B 123(3) . . ?

_refine_diff_density_max         0.267
_refine_diff_density_min         -0.283
_refine_diff_density_rms         0.059

_shelxl_version_number           2013-3
_database_code_depnum_ccdc_archive 'CCDC 970526'
#######################################################################
#
#                 Cambridge Crystallographic Data Centre
#                                CCDC 
# 
#######################################################################
# 
#  This CIF contains data from an original supplementary publication
#  deposited with the CCDC, and may include chemical, crystal,
#  experimental, refinement, atomic coordinates,
#  anisotropic displacement parameters and molecular geometry data,
#  as required by the journal to which it was submitted.
#
#  This CIF is provided on the understanding that it is used for bona
#  fide research purposes only. It may contain copyright material
#  of the CCDC or of third parties, and may not be copied or further
#  disseminated in any form, whether machine-readable or not,
#  except for the purpose of generating routine backup copies
#  on your local computer system.
# 
#  For further information on the CCDC, data deposition and
#  data retrieval see:
#                         www.ccdc.cam.ac.uk
#
#  Bona fide researchers may freely download Mercury and enCIFer
#  from this site to visualise CIF-encoded structures and 
#  to carry out CIF format checking respectively.
#
data_Compound_I

_audit_creation_method           
'SHELXL-2012 & Rigaku CrystalClear-SM Expert 2.0 r4'

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_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                   9.2392(2)
_cell_length_b                   20.2271(3)
_cell_length_c                   15.5813(4)
_cell_angle_alpha                90
_cell_angle_beta                 103.6380(10)
_cell_angle_gamma                90
_cell_volume                     2829.77(10)
_cell_formula_units_Z            4
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    13697
_cell_measurement_theta_min      1.7
_cell_measurement_theta_max      27.5

_exptl_crystal_F_000             1208
_exptl_crystal_description       Prism
_exptl_crystal_colour            Colorless
_exptl_crystal_size_max          0.40
_exptl_crystal_size_mid          0.22
_exptl_crystal_size_min          0.12
_chemical_formula_weight         581.19
_chemical_formula_analytical     ?
_chemical_formula_sum            'C38 H25 Cl1 S2 '
_exptl_absorpt_coefficient_mu    0.31
_exptl_absorpt_correction_type   Numerical
_exptl_absorpt_correction_T_max  0.974
_exptl_absorpt_correction_T_min  0.908
_exptl_absorpt_process_details   
;
'CrystalClear-SM Expert 2.0 r4 (Rigaku, 2009)'
;

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      293(2)
_diffrn_source_power             1.8
_diffrn_source_voltage           50.0
_diffrn_source_current           35.0
_diffrn_radiation_wavelength     0.71075
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  'Graphite Monochromator'
_diffrn_measurement_device       'Crystal Goniometer'
_diffrn_measurement_device_type  'Rigaku RAXIS II'
_diffrn_measurement_specimen_support Fiber
_diffrn_detector                 'Curved image plate'
_diffrn_measurement_method       'profile data from ω-scans'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_reflns_number            39024
_diffrn_reflns_av_unetI/netI     0.0442
_diffrn_reflns_av_R_equivalents  0.0640
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -26
_diffrn_reflns_limit_k_max       26
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_theta_min         2.268
_diffrn_reflns_theta_max         27.497
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measured_fraction_theta_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_point_group_measured_fraction_full 0.998
_reflns_number_total             6467
_reflns_number_gt                5149
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_computing_data_collection       
;
CrystalClear-SM Expert 2.0 r4 (Rigaku, 2009)
;
_computing_cell_refinement       
;
CrystalClear-SM Expert 2.0 r4 (Rigaku, 2009)
;
_computing_data_reduction        
;
CrystalClear-SM Expert 2.0 r4 (Rigaku, 2009)
;
_computing_structure_solution    'SHELXS-2013 (Sheldrick, 2013)'
_computing_structure_refinement  'SHELXL-2013 (Sheldrick, 2013)'
_computing_molecular_graphics    ?
_computing_publication_material  ?

_refine_special_details          
;
'Refinement of F² against ALL reflections.  The weighted R-factor wR and
 goodness of fit S are based on F², conventional R-factors R are based
 on F, with F set to zero for negative F². The threshold expression of
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is
 not relevant to the choice of reflections for refinement.  R-factors based
 on F² are statistically about twice as large as those based on F, and R-
 factors based on ALL data will be even larger.'
;
_diffrn_measurement_details      
;
scan:
	Number of images: 60
	           Slice: 20.0000 - 200.0000
	     Image width: 3.0000
	        Exp time: 300.0000
	   Rotation axis: Omega
	           Omega: 0.0000
	             Chi: 45.0000
	             Phi: 0.0000
	             XTD: 127.4000
	          2theta: -0.0284
scan:
	Number of images: 45
	           Slice: 53.0000 - 188.0000
	     Image width: 3.0000
	        Exp time: 300.0000
	   Rotation axis: Omega
	           Omega: 0.0000
	             Chi: 0.0000
	             Phi: 0.0000
	             XTD: 127.4000
	          2theta: -0.0284

;
_diffrn_orient_matrix_UB_11      -0.055431
_diffrn_orient_matrix_UB_12      0.029569
_diffrn_orient_matrix_UB_13      0.091965
_diffrn_orient_matrix_UB_21      -0.041260
_diffrn_orient_matrix_UB_22      0.005571
_diffrn_orient_matrix_UB_23      -0.026660
_diffrn_orient_matrix_UB_31      -0.022910
_diffrn_orient_matrix_UB_32      -0.057318
_diffrn_orient_matrix_UB_33      0.023479
_diffrn_orient_matrix_type       d*Trek


_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0357P)²+1.4942P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         6466
_refine_ls_number_parameters     350
_refine_ls_number_restraints     411
_refine_ls_R_factor_all          0.0773
_refine_ls_R_factor_gt           0.0592
_refine_ls_wR_factor_ref         0.1319
_refine_ls_wR_factor_gt          0.1231
_refine_ls_goodness_of_fit_ref   1.103
_refine_ls_restrained_S_all      1.088
_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
C1 C 0.68622(15) 0.69743(6) 0.70895(9) 0.0382(5) Uani 1 1 d G U . . .
C2 C 0.80618(16) 0.67477(6) 0.77383(10) 0.0435(5) Uani 1 1 d G U . . .
H2 H 0.8182 0.6297 0.7852 0.052 Uiso 1 1 calc R U . . .
C3 C 0.90825(14) 0.71946(8) 0.82177(10) 0.0548(7) Uani 1 1 d G U . . .
H3 H 0.9885 0.7043 0.8652 0.066 Uiso 1 1 calc R U . . .
C4 C 0.89036(17) 0.78680(8) 0.80483(11) 0.0609(7) Uani 1 1 d G U . . .
H4 H 0.9587 0.8167 0.8369 0.073 Uiso 1 1 calc R U . . .
C5 C 0.77040(19) 0.80946(5) 0.73994(12) 0.0593(7) Uani 1 1 d G U . . .
H5 H 0.7584 0.8545 0.7286 0.071 Uiso 1 1 calc R U . . .
C6 C 0.66833(16) 0.76478(7) 0.69200(10) 0.0467(6) Uani 1 1 d G U . . .
H6 H 0.5881 0.7799 0.6486 0.056 Uiso 1 1 calc R U . . .
C7 C 0.52758(15) 0.65448(7) 0.86694(9) 0.0379(5) Uani 1 1 d G U . . .
C8 C 0.63520(18) 0.62296(6) 0.93137(10) 0.0490(6) Uani 1 1 d G U . . .
H8 H 0.6417 0.5771 0.9321 0.059 Uiso 1 1 calc R U . . .
C9 C 0.73303(17) 0.66002(9) 0.99470(9) 0.0609(7) Uani 1 1 d G U . . .
H9 H 0.8050 0.6389 1.0378 0.073 Uiso 1 1 calc R U . . .
C10 C 0.72326(18) 0.72860(9) 0.99361(10) 0.0634(8) Uani 1 1 d G U . . .
H10 H 0.7887 0.7534 1.0360 0.076 Uiso 1 1 calc R U . . .
C11 C 0.6156(2) 0.76012(6) 0.92918(11) 0.0560(7) Uani 1 1 d G U . . .
H11 H 0.6091 0.8060 0.9285 0.067 Uiso 1 1 calc R U . . .
C12 C 0.51781(16) 0.72306(7) 0.86585(9) 0.0449(5) Uani 1 1 d G U . . .
H12 H 0.4458 0.7442 0.8227 0.054 Uiso 1 1 calc R U . . .
C13 C 0.29324(15) 0.58088(8) 0.83038(10) 0.0401(5) Uani 1 1 d G U . . .
C14 C 0.27186(18) 0.59673(8) 0.91332(9) 0.0504(6) Uani 1 1 d G U . . .
H14 H 0.3369 0.6257 0.9498 0.060 Uiso 1 1 calc R U . . .
C15 C 0.1533(2) 0.56934(10) 0.94176(10) 0.0674(8) Uani 1 1 d G U . . .
H15 H 0.1390 0.5799 0.9973 0.081 Uiso 1 1 calc R U . . .
C16 C 0.05613(18) 0.52611(10) 0.88728(13) 0.0736(9) Uani 1 1 d G U . . .
H16 H -0.0232 0.5078 0.9063 0.088 Uiso 1 1 calc R U . . .
C17 C 0.07751(18) 0.51026(9) 0.80434(12) 0.0658(8) Uani 1 1 d G U . . .
H17 H 0.0125 0.4813 0.7679 0.079 Uiso 1 1 calc R U . . .
C18 C 0.19607(18) 0.53764(8) 0.77589(9) 0.0520(6) Uani 1 1 d G U . . .
H18 H 0.2104 0.5270 0.7204 0.062 Uiso 1 1 calc R U . . .
C19 C 0.5690(2) 0.64893(10) 0.65517(14) 0.0360(5) Uani 1 1 d . U . . .
H19 H 0.5840 0.6479 0.5950 0.043 Uiso 1 1 calc R U . . .
C20 C 0.4113(2) 0.67287(10) 0.64840(14) 0.0364(5) Uani 1 1 d . U . . .
C21 C 0.3373(3) 0.71048(12) 0.57628(15) 0.0453(5) Uani 1 1 d . U . . .
H21 H 0.3826 0.7186 0.5300 0.054 Uiso 1 1 calc R U . . .
C22 C 0.1968(3) 0.73593(13) 0.57302(17) 0.0517(6) Uani 1 1 d . U . . .
H22 H 0.1478 0.7610 0.5248 0.062 Uiso 1 1 calc R U . . .
C23 C 0.1303(3) 0.72375(12) 0.64195(18) 0.0504(6) Uani 1 1 d . U . . .
H23 H 0.0376 0.7420 0.6412 0.060 Uiso 1 1 calc R U . . .
C24 C 0.2010(3) 0.68447(11) 0.71236(16) 0.0430(5) Uani 1 1 d . U . . .
H24 H 0.1541 0.6760 0.7579 0.052 Uiso 1 1 calc R U . . .
C25 C 0.3418(2) 0.65742(10) 0.71591(14) 0.0351(5) Uani 1 1 d . U . . .
C26 C 0.4202(2) 0.61276(11) 0.79398(14) 0.0353(5) Uani 1 1 d . U . . .
C27 C 0.5148(2) 0.55995(10) 0.75828(14) 0.0356(5) Uani 1 1 d . U . . .
C28 C 0.5405(2) 0.49591(11) 0.79144(15) 0.0400(5) Uani 1 1 d . U . . .
C29 C 0.6237(3) 0.45115(11) 0.75410(16) 0.0418(5) Uani 1 1 d . U . . .
C30 C 0.7601(3) 0.35999(13) 0.7057(2) 0.0671(8) Uani 1 1 d . U . . .
H30 H 0.8053 0.3204 0.6966 0.081 Uiso 1 1 calc R U . . .
C31 C 0.7628(3) 0.41394(12) 0.6559(2) 0.0553(7) Uani 1 1 d . U . . .
H31 H 0.8094 0.4157 0.6091 0.066 Uiso 1 1 calc R U . . .
C32 C 0.6852(2) 0.46874(11) 0.68346(16) 0.0408(5) Uani 1 1 d . U . . .
C33 C 0.6685(2) 0.53416(10) 0.65224(14) 0.0362(5) Uani 1 1 d D U . . .
C34 C 0.5851(2) 0.57851(10) 0.68928(14) 0.0336(4) Uani 1 1 d . U . . .
S2 S 0.66589(9) 0.37035(3) 0.78795(6) 0.0626(2) Uani 1 1 d . U . . .
Cl1 Cl 0.48307(8) 0.46380(3) 0.88221(4) 0.05620(19) Uani 1 1 d . U . . .
C35A C 0.7443(3) 0.55369(13) 0.58169(18) 0.0373(6) Uani 0.914(2) 1 d D U P A 1
C36A C 0.8752(7) 0.5830(3) 0.5857(4) 0.0697(3) Uani 0.914(2) 1 d D U P A 1
H36A H 0.9365 0.5957 0.6395 0.084 Uiso 0.914(2) 1 calc R U P A 1
C37A C 0.9163(4) 0.5941(2) 0.5071(2) 0.0612(9) Uani 0.914(2) 1 d D U P A 1
H37A H 1.0016 0.6167 0.5021 0.073 Uiso 0.914(2) 1 calc R U P A 1
C38A C 0.8165(4) 0.56763(18) 0.4391(2) 0.0630(9) Uani 0.914(2) 1 d D U P A 1
H38A H 0.8253 0.5684 0.3809 0.076 Uiso 0.914(2) 1 calc R U P A 1
S1A S 0.67085(12) 0.53223(5) 0.47274(6) 0.0697(3) Uani 0.914(2) 1 d D U P A 1
C35B C 0.714(2) 0.5525(8) 0.5696(13) 0.0373(6) Uani 0.086(2) 1 d D U P A 2
S1B S 0.8846(11) 0.5928(4) 0.5984(6) 0.0368(19) Uani 0.086(2) 1 d D U P A 2
C38B C 0.882(5) 0.584(3) 0.4867(16) 0.0612(9) Uani 0.086(2) 1 d D U P A 2
H38B H 0.9650 0.5909 0.4642 0.073 Uiso 0.086(2) 1 calc R U P A 2
C37B C 0.750(4) 0.565(2) 0.436(3) 0.0630(9) Uani 0.086(2) 1 d D U P A 2
H37B H 0.7304 0.5625 0.3746 0.076 Uiso 0.086(2) 1 calc R U P A 2
C36B C 0.644(4) 0.5506(16) 0.4841(17) 0.0368(19) Uani 0.086(2) 1 d D U P A 2
H36B H 0.5434 0.5414 0.4611 0.044 Uiso 0.086(2) 1 calc R U P A 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
C1 C2 1.3900 . ?
C1 C6 1.3900 . ?
C1 C19 1.552(2) . ?
C2 C3 1.3900 . ?
C3 C4 1.3900 . ?
C4 C5 1.3900 . ?
C5 C6 1.3900 . ?
C7 C8 1.3900 . ?
C7 C12 1.3900 . ?
C7 C26 1.568(2) . ?
C8 C9 1.3900 . ?
C9 C10 1.3900 . ?
C10 C11 1.3900 . ?
C11 C12 1.3900 . ?
C13 C14 1.3900 . ?
C13 C18 1.3900 . ?
C13 C26 1.558(2) . ?
C14 C15 1.3900 . ?
C15 C16 1.3900 . ?
C16 C17 1.3900 . ?
C17 C18 1.3900 . ?
C19 C20 1.515(3) . ?
C19 C34 1.515(3) . ?
C20 C25 1.391(3) . ?
C20 C21 1.395(3) . ?
C21 C22 1.386(3) . ?
C22 C23 1.379(4) . ?
C23 C24 1.387(3) . ?
C24 C25 1.401(3) . ?
C25 C26 1.551(3) . ?
C26 C27 1.563(3) . ?
C27 C28 1.394(3) . ?
C27 C34 1.431(3) . ?
C28 C29 1.400(3) . ?
C28 Cl1 1.749(2) . ?
C29 C32 1.399(3) . ?
C29 S2 1.733(2) . ?
C30 C31 1.343(4) . ?
C30 S2 1.724(3) . ?
C31 C32 1.440(3) . ?
C32 C33 1.406(3) . ?
C33 C34 1.394(3) . ?
C33 C35A 1.489(3) . ?
C33 C35B 1.493(18) . ?
C35A C36A 1.335(6) . ?
C35A S1A 1.728(3) . ?
C36A C37A 1.384(6) . ?
C37A C38A 1.340(4) . ?
C38A S1A 1.712(3) . ?
C35B C36B 1.34(2) . ?
C35B S1B 1.734(19) . ?
S1B C38B 1.74(2) . ?
C38B C37B 1.34(2) . ?
C37B C36B 1.40(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
C2 C1 C6 120.0 . . ?
C2 C1 C19 121.30(12) . . ?
C6 C1 C19 118.69(12) . . ?
C3 C2 C1 120.0 . . ?
C2 C3 C4 120.0 . . ?
C5 C4 C3 120.0 . . ?
C4 C5 C6 120.0 . . ?
C5 C6 C1 120.0 . . ?
C8 C7 C12 120.0 . . ?
C8 C7 C26 119.97(12) . . ?
C12 C7 C26 120.01(12) . . ?
C7 C8 C9 120.0 . . ?
C10 C9 C8 120.0 . . ?
C9 C10 C11 120.0 . . ?
C12 C11 C10 120.0 . . ?
C11 C12 C7 120.0 . . ?
C14 C13 C18 120.0 . . ?
C14 C13 C26 121.82(12) . . ?
C18 C13 C26 118.12(12) . . ?
C13 C14 C15 120.0 . . ?
C16 C15 C14 120.0 . . ?
C17 C16 C15 120.0 . . ?
C16 C17 C18 120.0 . . ?
C17 C18 C13 120.0 . . ?
C20 C19 C34 109.75(17) . . ?
C20 C19 C1 111.89(16) . . ?
C34 C19 C1 113.98(16) . . ?
C25 C20 C21 120.4(2) . . ?
C25 C20 C19 118.90(19) . . ?
C21 C20 C19 120.7(2) . . ?
C22 C21 C20 120.6(2) . . ?
C23 C22 C21 119.4(2) . . ?
C22 C23 C24 120.4(2) . . ?
C23 C24 C25 121.0(2) . . ?
C20 C25 C24 118.2(2) . . ?
C20 C25 C26 120.71(18) . . ?
C24 C25 C26 121.1(2) . . ?
C25 C26 C13 105.92(16) . . ?
C25 C26 C27 108.41(17) . . ?
C13 C26 C27 112.25(16) . . ?
C25 C26 C7 110.73(16) . . ?
C13 C26 C7 111.16(15) . . ?
C27 C26 C7 108.33(16) . . ?
C28 C27 C34 117.0(2) . . ?
C28 C27 C26 124.33(19) . . ?
C34 C27 C26 118.62(18) . . ?
C27 C28 C29 120.6(2) . . ?
C27 C28 Cl1 125.95(18) . . ?
C29 C28 Cl1 113.39(17) . . ?
C32 C29 C28 121.8(2) . . ?
C32 C29 S2 112.04(17) . . ?
C28 C29 S2 126.13(19) . . ?
C31 C30 S2 114.4(2) . . ?
C30 C31 C32 112.0(3) . . ?
C29 C32 C33 118.7(2) . . ?
C29 C32 C31 111.3(2) . . ?
C33 C32 C31 130.0(2) . . ?
C34 C33 C32 119.2(2) . . ?
C34 C33 C35A 122.5(2) . . ?
C32 C33 C35A 118.2(2) . . ?
C34 C33 C35B 119.6(7) . . ?
C32 C33 C35B 120.1(6) . . ?
C33 C34 C27 122.39(19) . . ?
C33 C34 C19 118.55(19) . . ?
C27 C34 C19 119.06(18) . . ?
C30 S2 C29 90.30(13) . . ?
C36A C35A C33 131.4(3) . . ?
C36A C35A S1A 107.4(3) . . ?
C33 C35A S1A 120.94(18) . . ?
C35A C36A C37A 117.7(4) . . ?
C38A C37A C36A 110.7(4) . . ?
C37A C38A S1A 111.7(3) . . ?
C38A S1A C35A 92.30(16) . . ?
C36B C35B C33 133(2) . . ?
C36B C35B S1B 118.0(19) . . ?
C33 C35B S1B 108.5(13) . . ?
C35B S1B C38B 83.8(16) . . ?
C37B C38B S1B 115(3) . . ?
C38B C37B C36B 113(4) . . ?
C35B C36B C37B 107(3) . . ?

_refine_diff_density_max         0.311
_refine_diff_density_min         -0.337
_refine_diff_density_rms         0.042

_shelxl_version_number           2013-3
_database_code_depnum_ccdc_archive 'CCDC 970527'
#######################################################################
#
#                 Cambridge Crystallographic Data Centre
#                                CCDC 
# 
#######################################################################
# 
#  This CIF contains data from an original supplementary publication
#  deposited with the CCDC, and may include chemical, crystal,
#  experimental, refinement, atomic coordinates,
#  anisotropic displacement parameters and molecular geometry data,
#  as required by the journal to which it was submitted.
#
#  This CIF is provided on the understanding that it is used for bona
#  fide research purposes only. It may contain copyright material
#  of the CCDC or of third parties, and may not be copied or further
#  disseminated in any form, whether machine-readable or not,
#  except for the purpose of generating routine backup copies
#  on your local computer system.
# 
#  For further information on the CCDC, data deposition and
#  data retrieval see:
#                         www.ccdc.cam.ac.uk
#
#  Bona fide researchers may freely download Mercury and enCIFer
#  from this site to visualise CIF-encoded structures and 
#  to carry out CIF format checking respectively.
#
data_Compound_L

_audit_creation_method           
'SHELXL-2012 & Rigaku CrystalClear-SM Expert 2.0 r4'

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'
S S 0.1246 0.1234 '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'

_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                   16.3862(10)
_cell_length_b                   8.9089(6)
_cell_length_c                   19.3895(14)
_cell_angle_alpha                90
_cell_angle_beta                 98.168(3)
_cell_angle_gamma                90
_cell_volume                     2801.8(3)
_cell_formula_units_Z            4
_cell_measurement_temperature    253(2)
_cell_measurement_reflns_used    13465
_cell_measurement_theta_min      2.1
_cell_measurement_theta_max      27.5

_exptl_crystal_description       Prism
_exptl_crystal_colour            Colorless
_exptl_crystal_size_max          0.50
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.18
_chemical_formula_weight         579.17
_chemical_formula_analytical     ?
_chemical_formula_sum            'C38 H23 Cl1 S2 '
_exptl_absorpt_coefficient_mu    0.313
_exptl_absorpt_correction_type   'Numerical integration'
_exptl_absorpt_correction_T_max  0.955
_exptl_absorpt_correction_T_min  0.891
_exptl_crystal_F_000             1200
_exptl_absorpt_process_details   
;
'CrystalClear-SM Expert 2.0 r4 (Rigaku, 2009)'
;

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      253(2)
_diffrn_source_power             1.8
_diffrn_source_voltage           50.0
_diffrn_source_current           35.0
_diffrn_radiation_wavelength     0.71075
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  'Graphite Monochromator'
_diffrn_measurement_device       'Crystal Goniometer'
_diffrn_measurement_device_type  'Rigaku RAXIS II'
_diffrn_measurement_specimen_support Fiber
_diffrn_detector                 'Curved image plate'
_diffrn_measurement_method       'profile data from ω-scans'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_reflns_number            26350
_diffrn_reflns_av_unetI/netI     0.0761
_diffrn_reflns_av_R_equivalents  0.0616
_diffrn_reflns_limit_h_min       -21
_diffrn_reflns_limit_h_max       21
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_l_min       -25
_diffrn_reflns_limit_l_max       25
_diffrn_reflns_theta_min         2.122
_diffrn_reflns_theta_max         27.510
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.992
_diffrn_measured_fraction_theta_full 0.995
_diffrn_reflns_Laue_measured_fraction_max 0.992
_diffrn_reflns_Laue_measured_fraction_full 0.995
_diffrn_reflns_point_group_measured_fraction_max 0.992
_diffrn_reflns_point_group_measured_fraction_full 0.995
_reflns_number_total             6404
_reflns_number_gt                4907
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_computing_data_collection       
;
CrystalClear-SM Expert 2.0 r4 (Rigaku, 2009)
;
_computing_cell_refinement       
;
CrystalClear-SM Expert 2.0 r4 (Rigaku, 2009)
;
_computing_data_reduction        
;
CrystalClear-SM Expert 2.0 r4 (Rigaku, 2009)
;
_computing_structure_solution    'SHELXS-2013 (Sheldrick, 2013)'
_computing_structure_refinement  'SHELXL-2013 (Sheldrick, 2013)'
_computing_molecular_graphics    ?
_computing_publication_material  ?

_diffrn_measurement_details      
;
scan:
	Number of images: 50
	           Slice: 20.0000 - 170.0000
	     Image width: 3.0000
	        Exp time: 300.0000
	   Rotation axis: Omega
	           Omega: 0.0000
	             Chi: 54.0000
	             Phi: 180.0000
	             XTD: 127.4000
	          2theta: -0.0313
scan:
	Number of images: 25
	           Slice: 95.0000 - 170.0000
	     Image width: 3.0000
	        Exp time: 300.0000
	   Rotation axis: Omega
	           Omega: 0.0000
	             Chi: 0.0000
	             Phi: 0.0000
	             XTD: 127.4000
	          2theta: -0.0313

;
_diffrn_orient_matrix_UB_11      0.051438
_diffrn_orient_matrix_UB_12      -0.061577
_diffrn_orient_matrix_UB_13      0.009642
_diffrn_orient_matrix_UB_21      -0.002517
_diffrn_orient_matrix_UB_22      0.006837
_diffrn_orient_matrix_UB_23      0.051098
_diffrn_orient_matrix_UB_31      -0.033917
_diffrn_orient_matrix_UB_32      -0.093893
_diffrn_orient_matrix_UB_33      -0.002603
_diffrn_orient_matrix_type       FS_PROCESS
_refine_special_details          
;
'Refinement of F² against ALL reflections.  The weighted R-factor wR and
 goodness of fit S are based on F², conventional R-factors R are based
 on F, with F set to zero for negative F². The threshold expression of
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is
 not relevant to the choice of reflections for refinement.  R-factors based
 on F² are statistically about twice as large as those based on F, and R-
 factors based on ALL data will be even larger.'
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0456P)²+1.7050P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     SHELXL
_refine_ls_extinction_coef       0.0097(11)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         6404
_refine_ls_number_parameters     371
_refine_ls_number_restraints     375
_refine_ls_R_factor_all          0.0948
_refine_ls_R_factor_gt           0.0704
_refine_ls_wR_factor_ref         0.1701
_refine_ls_wR_factor_gt          0.1477
_refine_ls_goodness_of_fit_ref   1.147
_refine_ls_restrained_S_all      1.133
_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
C1 C 0.26370(16) 0.8165(3) 0.35253(14) 0.0440(6) Uani 1 1 d . U . . .
C2 C 0.33527(18) 0.8889(3) 0.38183(16) 0.0538(7) Uani 1 1 d . U . . .
H2 H 0.3672 0.8473 0.4213 0.065 Uiso 1 1 calc R U . . .
C3 C 0.3608(2) 1.0221(4) 0.35387(19) 0.0627(8) Uani 1 1 d . U . . .
H3 H 0.4099 1.0689 0.3740 0.075 Uiso 1 1 calc R U . . .
C4 C 0.3139(2) 1.0850(4) 0.29651(18) 0.0650(9) Uani 1 1 d . U . . .
H4 H 0.3313 1.1738 0.2769 0.078 Uiso 1 1 calc R U . . .
C5 C 0.2416(2) 1.0173(4) 0.26822(17) 0.0604(8) Uani 1 1 d . U . . .
H5 H 0.2085 1.0621 0.2302 0.072 Uiso 1 1 calc R U . . .
C6 C 0.21667(19) 0.8823(3) 0.29543(15) 0.0512(7) Uani 1 1 d . U . . .
H6 H 0.1677 0.8358 0.2749 0.061 Uiso 1 1 calc R U . . .
C7 C 0.16361(16) 0.5972(3) 0.34077(15) 0.0462(6) Uani 1 1 d . U . . .
C8 C 0.08437(18) 0.6155(4) 0.35649(18) 0.0614(8) Uani 1 1 d . U . . .
H8 H 0.0756 0.6725 0.3955 0.074 Uiso 1 1 calc R U . . .
C9 C 0.0174(2) 0.5497(5) 0.3147(2) 0.0812(11) Uani 1 1 d . U . . .
H9 H -0.0360 0.5633 0.3261 0.097 Uiso 1 1 calc R U . . .
C10 C 0.0282(2) 0.4659(5) 0.2577(2) 0.0772(10) Uani 1 1 d . U . . .
H10 H -0.0172 0.4205 0.2305 0.093 Uiso 1 1 calc R U . . .
C11 C 0.1057(2) 0.4493(4) 0.24089(19) 0.0700(9) Uani 1 1 d . U . . .
H11 H 0.1136 0.3944 0.2010 0.084 Uiso 1 1 calc R U . . .
C12 C 0.17277(19) 0.5121(4) 0.28179(16) 0.0560(7) Uani 1 1 d . U . . .
H12 H 0.2258 0.4974 0.2697 0.067 Uiso 1 1 calc R U . . .
C13 C 0.17455(16) 0.3509(3) 0.46656(14) 0.0433(6) Uani 1 1 d . U . . .
C14 C 0.1041(2) 0.3604(4) 0.49867(18) 0.0640(9) Uani 1 1 d . U . . .
H14 H 0.1038 0.4235 0.5375 0.077 Uiso 1 1 calc R U . . .
C15 C 0.0342(2) 0.2776(4) 0.4741(2) 0.0761(11) Uani 1 1 d . U . . .
H15 H -0.0130 0.2855 0.4964 0.091 Uiso 1 1 calc R U . . .
C16 C 0.0334(2) 0.1843(4) 0.4176(2) 0.0670(9) Uani 1 1 d . U . . .
H16 H -0.0140 0.1284 0.4010 0.080 Uiso 1 1 calc R U . . .
C17 C 0.10284(18) 0.1740(3) 0.38569(18) 0.0557(7) Uani 1 1 d . U . . .
H17 H 0.1025 0.1114 0.3466 0.067 Uiso 1 1 calc R U . . .
C18 C 0.17335(16) 0.2541(3) 0.41019(15) 0.0472(6) Uani 1 1 d . U . . .
H18 H 0.2208 0.2430 0.3885 0.057 Uiso 1 1 calc R U . . .
C19 C 0.23104(15) 0.5977(3) 0.51427(14) 0.0412(6) Uani 1 1 d . U . . .
C20 C 0.21839(17) 0.6385(3) 0.58150(15) 0.0492(7) Uani 1 1 d . U . . .
H20 H 0.2258 0.5664 0.6173 0.059 Uiso 1 1 calc R U . . .
C21 C 0.19518(19) 0.7830(3) 0.59655(17) 0.0558(7) Uani 1 1 d . U . . .
H21 H 0.1877 0.8093 0.6422 0.067 Uiso 1 1 calc R U . . .
C22 C 0.18328(19) 0.8876(3) 0.54369(18) 0.0581(8) Uani 1 1 d . U . . .
H22 H 0.1661 0.9853 0.5530 0.070 Uiso 1 1 calc R U . . .
C23 C 0.19657(18) 0.8496(3) 0.47673(17) 0.0524(7) Uani 1 1 d . U . . .
H23 H 0.1886 0.9224 0.4413 0.063 Uiso 1 1 calc R U . . .
C24 C 0.22164(15) 0.7049(3) 0.46079(14) 0.0420(6) Uani 1 1 d . U . . .
C25 C 0.23958(15) 0.6679(3) 0.38528(14) 0.0413(6) Uani 1 1 d . U . . .
C26 C 0.31214(15) 0.5551(3) 0.39213(14) 0.0400(6) Uani 1 1 d . U . . .
C27 C 0.37608(17) 0.5476(3) 0.35087(15) 0.0466(6) Uani 1 1 d . U . . .
C28 C 0.44302(16) 0.4513(3) 0.36884(17) 0.0523(7) Uani 1 1 d . U . . .
C29 C 0.45143(16) 0.3610(3) 0.42892(17) 0.0533(7) Uani 1 1 d . U . . .
C30 C 0.38602(16) 0.3631(3) 0.46798(15) 0.0466(6) Uani 1 1 d . U . . .
C31 C 0.31705(15) 0.4526(3) 0.44667(14) 0.0406(6) Uani 1 1 d . U . . .
C32 C 0.25321(16) 0.4385(3) 0.49638(14) 0.0411(6) Uani 1 1 d . U . . .
C33 C 0.30001(19) 0.3381(3) 0.55321(15) 0.0506(7) Uani 1 1 d . U . . .
C34 C 0.2827(2) 0.2640(4) 0.61389(17) 0.0674(9) Uani 1 1 d . U . . .
H34 H 0.2345 0.2782 0.6343 0.081 Uiso 1 1 calc R U . . .
C35 C 0.3456(3) 0.1683(4) 0.6390(2) 0.0838(12) Uani 1 1 d . U . . .
H35 H 0.3456 0.1101 0.6795 0.101 Uiso 1 1 calc R U . . .
C36 C 0.37327(19) 0.2938(3) 0.53310(16) 0.0555(7) Uani 1 1 d . U . . .
C37 C 0.52722(19) 0.2767(4) 0.4373(2) 0.0725(10) Uani 1 1 d . U . . .
H37 H 0.5441 0.2121 0.4749 0.087 Uiso 1 1 calc R U . . .
C38 C 0.5710(2) 0.3017(5) 0.3847(2) 0.0839(12) Uani 1 1 d . U . . .
H38 H 0.6215 0.2540 0.3816 0.101 Uiso 1 1 calc R U . . .
S1 S 0.42407(7) 0.16546(11) 0.58964(6) 0.0820(3) Uani 1 1 d . U . . .
S2 S 0.52653(5) 0.42879(12) 0.32350(6) 0.0804(3) Uani 1 1 d . U . . .
Cl1 Cl 0.37806(5) 0.64610(9) 0.27352(4) 0.0662(3) Uani 1 1 d . 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
C1 C6 1.386(4) . ?
C1 C2 1.387(4) . ?
C1 C25 1.544(4) . ?
C2 C3 1.394(4) . ?
C3 C4 1.378(5) . ?
C4 C5 1.372(5) . ?
C5 C6 1.397(4) . ?
C7 C8 1.385(4) . ?
C7 C12 1.398(4) . ?
C7 C25 1.545(4) . ?
C8 C9 1.397(5) . ?
C9 C10 1.366(6) . ?
C10 C11 1.364(5) . ?
C11 C12 1.379(4) . ?
C13 C14 1.389(4) . ?
C13 C18 1.390(4) . ?
C13 C32 1.547(4) . ?
C14 C15 1.389(5) . ?
C15 C16 1.374(5) . ?
C16 C17 1.373(4) . ?
C17 C18 1.384(4) . ?
C19 C20 1.397(4) . ?
C19 C24 1.402(4) . ?
C19 C32 1.516(4) . ?
C20 C21 1.385(4) . ?
C21 C22 1.379(5) . ?
C22 C23 1.389(4) . ?
C23 C24 1.401(4) . ?
C24 C25 1.569(4) . ?
C25 C26 1.549(3) . ?
C26 C31 1.391(4) . ?
C26 C27 1.407(3) . ?
C27 C28 1.397(4) . ?
C27 Cl1 1.742(3) . ?
C28 C29 1.406(5) . ?
C28 S2 1.740(3) . ?
C29 C30 1.398(4) . ?
C29 C37 1.440(4) . ?
C30 C31 1.397(4) . ?
C30 C36 1.447(4) . ?
C31 C32 1.525(3) . ?
C32 C33 1.537(4) . ?
C33 C36 1.372(4) . ?
C33 C34 1.413(4) . ?
C34 C35 1.373(5) . ?
C35 S1 1.708(5) . ?
C36 S1 1.716(3) . ?
C37 C38 1.346(6) . ?
C38 S2 1.725(5) . ?

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
C6 C1 C2 118.2(3) . . ?
C6 C1 C25 123.0(2) . . ?
C2 C1 C25 118.8(2) . . ?
C1 C2 C3 121.3(3) . . ?
C4 C3 C2 119.7(3) . . ?
C5 C4 C3 119.7(3) . . ?
C4 C5 C6 120.6(3) . . ?
C1 C6 C5 120.4(3) . . ?
C8 C7 C12 117.2(3) . . ?
C8 C7 C25 122.4(3) . . ?
C12 C7 C25 120.4(2) . . ?
C7 C8 C9 120.5(3) . . ?
C10 C9 C8 121.1(3) . . ?
C11 C10 C9 119.0(3) . . ?
C10 C11 C12 120.8(4) . . ?
C11 C12 C7 121.4(3) . . ?
C14 C13 C18 118.0(3) . . ?
C14 C13 C32 120.2(3) . . ?
C18 C13 C32 121.7(2) . . ?
C15 C14 C13 120.8(3) . . ?
C16 C15 C14 120.6(3) . . ?
C17 C16 C15 119.0(3) . . ?
C16 C17 C18 121.1(3) . . ?
C17 C18 C13 120.5(3) . . ?
C20 C19 C24 119.8(2) . . ?
C20 C19 C32 121.9(2) . . ?
C24 C19 C32 118.2(2) . . ?
C21 C20 C19 121.3(3) . . ?
C22 C21 C20 119.1(3) . . ?
C21 C22 C23 120.4(3) . . ?
C22 C23 C24 121.4(3) . . ?
C23 C24 C19 118.0(3) . . ?
C23 C24 C25 119.9(2) . . ?
C19 C24 C25 122.1(2) . . ?
C1 C25 C7 110.7(2) . . ?
C1 C25 C26 110.7(2) . . ?
C7 C25 C26 109.3(2) . . ?
C1 C25 C24 107.3(2) . . ?
C7 C25 C24 111.3(2) . . ?
C26 C25 C24 107.4(2) . . ?
C31 C26 C27 115.7(2) . . ?
C31 C26 C25 116.9(2) . . ?
C27 C26 C25 127.4(2) . . ?
C28 C27 C26 120.6(3) . . ?
C28 C27 Cl1 114.5(2) . . ?
C26 C27 Cl1 124.9(2) . . ?
C27 C28 C29 122.6(2) . . ?
C27 C28 S2 126.2(3) . . ?
C29 C28 S2 111.2(2) . . ?
C30 C29 C28 116.6(3) . . ?
C30 C29 C37 131.4(3) . . ?
C28 C29 C37 111.9(3) . . ?
C31 C30 C29 119.9(3) . . ?
C31 C30 C36 106.9(2) . . ?
C29 C30 C36 133.1(3) . . ?
C26 C31 C30 123.8(2) . . ?
C26 C31 C32 124.3(2) . . ?
C30 C31 C32 111.4(2) . . ?
C19 C32 C31 106.0(2) . . ?
C19 C32 C33 119.5(2) . . ?
C31 C32 C33 100.6(2) . . ?
C19 C32 C13 110.1(2) . . ?
C31 C32 C13 114.5(2) . . ?
C33 C32 C13 106.2(2) . . ?
C36 C33 C34 113.0(3) . . ?
C36 C33 C32 109.3(3) . . ?
C34 C33 C32 136.9(3) . . ?
C35 C34 C33 110.8(3) . . ?
C34 C35 S1 113.4(3) . . ?
C33 C36 C30 111.5(3) . . ?
C33 C36 S1 112.0(2) . . ?
C30 C36 S1 136.5(2) . . ?
C38 C37 C29 111.8(4) . . ?
C37 C38 S2 114.3(3) . . ?
C35 S1 C36 90.74(17) . . ?
C38 S2 C28 90.78(18) . . ?

_refine_diff_density_max         0.474
_refine_diff_density_min         -0.392
_refine_diff_density_rms         0.055

_shelxl_version_number           2013-3

_database_code_depnum_ccdc_archive 'CCDC 970528'
#######################################################################
#
#                 Cambridge Crystallographic Data Centre
#                                CCDC 
# 
#######################################################################
# 
#  This CIF contains data from an original supplementary publication
#  deposited with the CCDC, and may include chemical, crystal,
#  experimental, refinement, atomic coordinates,
#  anisotropic displacement parameters and molecular geometry data,
#  as required by the journal to which it was submitted.
#
#  This CIF is provided on the understanding that it is used for bona
#  fide research purposes only. It may contain copyright material
#  of the CCDC or of third parties, and may not be copied or further
#  disseminated in any form, whether machine-readable or not,
#  except for the purpose of generating routine backup copies
#  on your local computer system.
# 
#  For further information on the CCDC, data deposition and
#  data retrieval see:
#                         www.ccdc.cam.ac.uk
#
#  Bona fide researchers may freely download Mercury and enCIFer
#  from this site to visualise CIF-encoded structures and 
#  to carry out CIF format checking respectively.
#
data_Compound_N

_audit_creation_method           
'SHELXL-2012 & Rigaku CrystalClear-SM Expert 2.0 r4'

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'
S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      monoclinic
_space_group_IT_number           4
_space_group_name_H-M_alt        'P 21'
_space_group_name_Hall           'P 2yb'

_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'



_cell_length_a                   11.5180(6)
_cell_length_b                   6.0678(3)
_cell_length_c                   20.8427(10)
_cell_angle_alpha                90
_cell_angle_beta                 93.276(3)
_cell_angle_gamma                90
_cell_volume                     1454.29(12)
_cell_formula_units_Z            2
_cell_measurement_temperature    253(2)
_cell_measurement_reflns_used    4594
_cell_measurement_theta_min      2.0
_cell_measurement_theta_max      27.5

_exptl_crystal_F_000             572
_exptl_crystal_description       Needle
_exptl_crystal_colour            Yellow
_exptl_crystal_size_max          0.80
_exptl_crystal_size_mid          0.10
_exptl_crystal_size_min          0.08
_chemical_formula_weight         546.73
_chemical_formula_analytical     ?
_chemical_formula_sum            'C38 H26 S2 '
_exptl_absorpt_coefficient_mu    0.21
_exptl_absorpt_correction_type   Numerical
_exptl_absorpt_correction_T_max  0.988
_exptl_absorpt_correction_T_min  0.956
_exptl_absorpt_process_details   
;
'CrystalClear-SM Expert 2.0 r4 (Rigaku, 2009)'
;
_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      253(2)
_diffrn_source_power             1.8
_diffrn_source_voltage           50.0
_diffrn_source_current           35.0
_diffrn_radiation_wavelength     0.71075
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  'Graphite Monochromator'
_diffrn_measurement_device       'Crystal Goniometer'
_diffrn_measurement_device_type  'Rigaku RAXIS II'
_diffrn_measurement_specimen_support Fiber
_diffrn_detector                 'Curved image plate'
_diffrn_measurement_method       'profile data from ω-scans'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_reflns_number            14547
_diffrn_reflns_av_unetI/netI     0.0801
_diffrn_reflns_av_R_equivalents  0.0550
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_l_min       -27
_diffrn_reflns_limit_l_max       27
_diffrn_reflns_theta_min         2.714
_diffrn_reflns_theta_max         27.499
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measured_fraction_theta_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_point_group_measured_fraction_full 0.997
_reflns_number_total             6467
_reflns_number_gt                4379
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.828
_reflns_Friedel_fraction_max     0.998
_reflns_Friedel_fraction_full    0.998

_computing_data_collection       
;
CrystalClear-SM Expert 2.0 r4 (Rigaku, 2009)
;
_computing_cell_refinement       
;
CrystalClear-SM Expert 2.0 r4 (Rigaku, 2009)
;
_computing_data_reduction        
;
CrystalClear-SM Expert 2.0 r4 (Rigaku, 2009)
;
_computing_structure_solution    'SHELXS-2013 (Sheldrick, 2013)'
_computing_structure_refinement  'SHELXL-2013 (Sheldrick, 2013)'
_computing_molecular_graphics    ?
_computing_publication_material  ?

_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.
;

_refine_special_details          
;
Refined as a 2-component perfect inversion twin.
;
_diffrn_measurement_details      
;
scan:
	Number of images: 40
	           Slice: 50.0000 - 170.0000
	     Image width: 3.0000
	        Exp time: 420.0000
	   Rotation axis: Omega
	           Omega: 0.0000
	             Chi: 45.0000
	             Phi: 90.0000
	             XTD: 127.4000
	          2theta: -0.0074
scan:
	Number of images: 35
	           Slice: 72.0000 - 177.0000
	     Image width: 3.0000
	        Exp time: 420.0000
	   Rotation axis: Omega
	           Omega: 0.0000
	             Chi: 30.0000
	             Phi: 0.0000
	             XTD: 127.4000
	          2theta: -0.0074

;
_diffrn_orient_matrix_UB_11      -0.029364
_diffrn_orient_matrix_UB_12      0.015735
_diffrn_orient_matrix_UB_13      0.080329
_diffrn_orient_matrix_UB_21      -0.155105
_diffrn_orient_matrix_UB_22      -0.013300
_diffrn_orient_matrix_UB_23      -0.054093
_diffrn_orient_matrix_UB_31      -0.000200
_diffrn_orient_matrix_UB_32      -0.046530
_diffrn_orient_matrix_UB_33      0.012015
_diffrn_orient_matrix_type       d*Trek

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0480P)²+0.4083P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     SHELXL
_refine_ls_extinction_coef       0.032(4)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_abs_structure_details 
;
 Refined as a perfect inversion twin.
;
_refine_ls_abs_structure_Flack   0.5
_chemical_absolute_configuration ?
_refine_ls_number_reflns         6467
_refine_ls_number_parameters     334
_refine_ls_number_restraints     431
_refine_ls_R_factor_all          0.1057
_refine_ls_R_factor_gt           0.0704
_refine_ls_wR_factor_ref         0.1679
_refine_ls_wR_factor_gt          0.1454
_refine_ls_goodness_of_fit_ref   1.055
_refine_ls_restrained_S_all      1.038
_refine_ls_shift/su_max          0.017
_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
C1A C 0.7037(13) 0.566(4) 0.7152(14) 0.084(3) Uani 0.616(7) 1 d D U P A 1
H1A H 0.7842 0.5733 0.7210 0.101 Uiso 0.616(7) 1 calc R U P A 1
C2A C 0.6500(15) 0.407(4) 0.6812(15) 0.081(3) Uani 0.616(7) 1 d D U P A 1
H2A H 0.6868 0.2896 0.6622 0.097 Uiso 0.616(7) 1 calc R U P A 1
C3A C 0.518(2) 0.447(5) 0.6781(15) 0.0796(18) Uani 0.616(7) 1 d D U P A 1
H3AA H 0.4620 0.3582 0.6568 0.096 Uiso 0.616(7) 1 calc R U P A 1
C4A C 0.4962(17) 0.630(8) 0.711(3) 0.055(2) Uani 0.616(7) 1 d D U P A 1
S1A S 0.6228(4) 0.7391(9) 0.7446(3) 0.0853(13) Uani 0.616(7) 1 d D U P A 1
C2B C 0.6998(19) 0.507(6) 0.708(2) 0.084(3) Uani 0.384(7) 1 d D U P A 2
H2B H 0.7803 0.5025 0.7153 0.101 Uiso 0.384(7) 1 calc R U P A 2
C1B C 0.635(2) 0.368(8) 0.673(3) 0.081(3) Uani 0.384(7) 1 d D U P A 2
H1B H 0.6675 0.2532 0.6509 0.097 Uiso 0.384(7) 1 calc R U P A 2
S1B S 0.5048(10) 0.4041(18) 0.6699(6) 0.0796(18) Uani 0.384(7) 1 d D U P A 2
C4B C 0.503(3) 0.644(13) 0.714(5) 0.055(2) Uani 0.384(7) 1 d D U P A 2
C3B C 0.615(2) 0.682(6) 0.7361(19) 0.0853(13) Uani 0.384(7) 1 d D U P A 2
H3BA H 0.6379 0.7959 0.7637 0.102 Uiso 0.384(7) 1 calc R U P A 2
C7C C 0.3305(17) 0.925(7) 0.6113(7) 0.054(4) Uani 0.698(7) 1 d D U P B 1
C8C C 0.2516(19) 0.998(7) 0.5662(10) 0.087(2) Uani 0.698(7) 1 d D U P B 1
H8CA H 0.1738 1.0256 0.5729 0.104 Uiso 0.698(7) 1 calc R U P B 1
C9C C 0.3062(13) 1.027(4) 0.5051(7) 0.085(3) Uani 0.698(7) 1 d D U P B 1
H9C H 0.2652 1.0702 0.4675 0.102 Uiso 0.698(7) 1 calc R U P B 1
C10C C 0.4194(14) 0.985(4) 0.5080(6) 0.079(3) Uani 0.698(7) 1 d D U P B 1
H10C H 0.4656 0.9932 0.4729 0.094 Uiso 0.698(7) 1 calc R U P B 1
S2C S 0.4700(3) 0.9146(10) 0.58351(15) 0.0779(10) Uani 0.698(7) 1 d D U P B 1
C7D C 0.341(4) 0.951(19) 0.6153(17) 0.054(4) Uani 0.302(7) 1 d D U P B 2
S2D S 0.2353(11) 1.002(4) 0.5548(5) 0.087(2) Uani 0.302(7) 1 d D U P B 2
C10D C 0.330(3) 1.026(11) 0.4955(15) 0.085(3) Uani 0.302(7) 1 d D U P B 2
H10D H 0.3095 1.0517 0.4523 0.102 Uiso 0.302(7) 1 calc R U P B 2
C9D C 0.439(3) 1.001(11) 0.5218(16) 0.079(3) Uani 0.302(7) 1 d D U P B 2
H9D H 0.5046 1.0243 0.4986 0.094 Uiso 0.302(7) 1 calc R U P B 2
C8D C 0.448(3) 0.932(10) 0.5911(15) 0.0779(10) Uani 0.302(7) 1 d D U P B 2
H8DA H 0.5152 0.8841 0.6138 0.094 Uiso 0.302(7) 1 calc R U P B 2
C5 C 0.3865(4) 0.7443(9) 0.7199(2) 0.0516(11) Uani 1 1 d D U . . .
C6 C 0.3164(4) 0.8678(9) 0.67886(19) 0.0500(11) Uani 1 1 d D U . . .
C11 C 0.2246(4) 0.8910(9) 0.72719(19) 0.0474(11) Uani 1 1 d . U . . .
C12 C 0.1139(4) 0.9636(8) 0.7240(2) 0.0478(11) Uani 1 1 d . U . . .
C13 C 0.07176(18) 1.1133(3) 0.67089(9) 0.0519(12) Uani 1 1 d G U . . .
C14 C 0.1288(2) 1.3113(4) 0.66108(11) 0.0691(15) Uani 1 1 d G U . . .
H14 H 0.1949 1.3478 0.6865 0.083 Uiso 1 1 calc R U . . .
C15 C 0.0869(3) 1.4549(4) 0.61320(12) 0.091(2) Uani 1 1 d G U . . .
H15 H 0.1250 1.5874 0.6066 0.109 Uiso 1 1 calc R U . . .
C16 C -0.0120(3) 1.4005(5) 0.57514(11) 0.092(2) Uani 1 1 d G U . . .
H16 H -0.0400 1.4965 0.5431 0.110 Uiso 1 1 calc R U . . .
C17 C -0.0690(3) 1.2024(6) 0.58495(9) 0.0821(18) Uani 1 1 d G U . . .
H17 H -0.1351 1.1660 0.5595 0.099 Uiso 1 1 calc R U . . .
C18 C -0.0271(2) 1.0589(4) 0.63282(7) 0.0683(15) Uani 1 1 d G U . . .
H18 H -0.0653 0.9264 0.6394 0.082 Uiso 1 1 calc R U . . .
C19 C 0.02676(16) 0.9051(4) 0.77119(8) 0.0487(11) Uani 1 1 d G U . . .
C20 C -0.05668(19) 1.0608(4) 0.78508(8) 0.0592(13) Uani 1 1 d G U . . .
H20 H -0.0553 1.1997 0.7663 0.071 Uiso 1 1 calc R U . . .
C21 C -0.1421(2) 1.0090(5) 0.82707(10) 0.0694(15) Uani 1 1 d G U . . .
H21 H -0.1980 1.1132 0.8364 0.083 Uiso 1 1 calc R U . . .
C22 C -0.1441(2) 0.8014(6) 0.85518(10) 0.0687(15) Uani 1 1 d G U . . .
H22 H -0.2013 0.7667 0.8833 0.082 Uiso 1 1 calc R U . . .
C23 C -0.0607(2) 0.6456(5) 0.84130(11) 0.0609(13) Uani 1 1 d G U . . .
H23 H -0.0620 0.5067 0.8601 0.073 Uiso 1 1 calc R U . . .
C24 C 0.0247(2) 0.6975(4) 0.79930(11) 0.0529(12) Uani 1 1 d G U . . .
H24 H 0.0806 0.5933 0.7900 0.064 Uiso 1 1 calc R U . . .
C25 C 0.3067(4) 0.7642(8) 0.7735(2) 0.0483(11) Uani 1 1 d . U . . .
C26 C 0.3201(4) 0.7133(8) 0.8369(2) 0.0471(11) Uani 1 1 d . U . . .
C27 C 0.24477(15) 0.7999(3) 0.88730(8) 0.0447(10) Uani 1 1 d G U . . .
C28 C 0.1980(2) 1.0111(3) 0.88605(11) 0.0533(12) Uani 1 1 d G U . . .
H28 H 0.2118 1.1056 0.8522 0.064 Uiso 1 1 calc R U . . .
C29 C 0.1306(2) 1.0811(4) 0.93541(12) 0.0613(13) Uani 1 1 d G U . . .
H29 H 0.0993 1.2224 0.9346 0.074 Uiso 1 1 calc R U . . .
C30 C 0.11007(19) 0.9399(5) 0.98603(11) 0.0659(14) Uani 1 1 d G U . . .
H30 H 0.0650 0.9867 1.0191 0.079 Uiso 1 1 calc R U . . .
C31 C 0.15685(18) 0.7287(4) 0.98729(10) 0.0618(14) Uani 1 1 d G U . . .
H31 H 0.1431 0.6342 1.0212 0.074 Uiso 1 1 calc R U . . .
C32 C 0.22420(14) 0.6587(3) 0.93793(9) 0.0535(12) Uani 1 1 d G U . . .
H32 H 0.2555 0.5173 0.9388 0.064 Uiso 1 1 calc R U . . .
C33 C 0.41698(16) 0.5603(3) 0.86016(8) 0.0499(11) Uani 1 1 d G U . . .
C34 C 0.4302(2) 0.3560(4) 0.83131(10) 0.0578(13) Uani 1 1 d G U . . .
H34 H 0.3811 0.3150 0.7964 0.069 Uiso 1 1 calc R U . . .
C35 C 0.5170(2) 0.2130(4) 0.85464(13) 0.0679(15) Uani 1 1 d G U . . .
H35 H 0.5258 0.0763 0.8353 0.081 Uiso 1 1 calc R U . . .
C36 C 0.5904(2) 0.2743(5) 0.90681(12) 0.0727(16) Uani 1 1 d G U . . .
H36 H 0.6485 0.1786 0.9224 0.087 Uiso 1 1 calc R U . . .
C37 C 0.57721(16) 0.4786(5) 0.93567(11) 0.0664(15) Uani 1 1 d G U . . .
H37 H 0.6264 0.5196 0.9706 0.080 Uiso 1 1 calc R U . . .
C38 C 0.49047(13) 0.6216(4) 0.91234(10) 0.0570(13) Uani 1 1 d G U . . .
H38 H 0.4816 0.7583 0.9316 0.068 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
C1A C2A 1.328(13) . ?
C1A S1A 1.552(13) . ?
C2A C3A 1.54(3) . ?
C3A C4A 1.34(4) . ?
C4A C5 1.461(11) . ?
C4A S1A 1.71(3) . ?
C2B C1B 1.324(18) . ?
C2B C3B 1.58(3) . ?
C1B S1B 1.51(2) . ?
S1B C4B 1.73(5) . ?
C4B C3B 1.36(4) . ?
C4B C5 1.486(16) . ?
C7C C8C 1.34(3) . ?
C7C C6 1.469(9) . ?
C7C S2C 1.74(2) . ?
C8C C9C 1.46(2) . ?
C9C C10C 1.325(13) . ?
C10C S2C 1.702(12) . ?
C7D C8D 1.36(4) . ?
C7D C6 1.46(2) . ?
C7D S2D 1.73(4) . ?
S2D C10D 1.70(2) . ?
C10D C9D 1.36(2) . ?
C9D C8D 1.50(3) . ?
C5 C6 1.366(7) . ?
C5 C25 1.493(6) . ?
C6 C11 1.508(6) . ?
C11 C12 1.347(6) . ?
C11 C25 1.521(6) . ?
C12 C19 1.488(5) . ?
C12 C13 1.492(5) . ?
C13 C14 1.3900 . ?
C13 C18 1.3900 . ?
C14 C15 1.3900 . ?
C15 C16 1.3900 . ?
C16 C17 1.3900 . ?
C17 C18 1.3900 . ?
C19 C20 1.3900 . ?
C19 C24 1.3900 . ?
C20 C21 1.3900 . ?
C21 C22 1.3900 . ?
C22 C23 1.3900 . ?
C23 C24 1.3900 . ?
C25 C26 1.356(6) . ?
C26 C27 1.496(5) . ?
C26 C33 1.510(5) . ?
C27 C28 1.3900 . ?
C27 C32 1.3900 . ?
C28 C29 1.3900 . ?
C29 C30 1.3900 . ?
C30 C31 1.3900 . ?
C31 C32 1.3900 . ?
C33 C34 1.3900 . ?
C33 C38 1.3900 . ?
C34 C35 1.3900 . ?
C35 C36 1.3900 . ?
C36 C37 1.3900 . ?
C37 C38 1.3900 . ?

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
C2A C1A S1A 115.4(14) . . ?
C1A C2A C3A 109.8(17) . . ?
C4A C3A C2A 109(2) . . ?
C3A C4A C5 130(2) . . ?
C3A C4A S1A 110.6(13) . . ?
C5 C4A S1A 119.1(19) . . ?
C1A S1A C4A 95.4(9) . . ?
C1B C2B C3B 107(2) . . ?
C2B C1B S1B 118(2) . . ?
C1B S1B C4B 98.0(17) . . ?
C3B C4B C5 138(4) . . ?
C3B C4B S1B 106.4(17) . . ?
C5 C4B S1B 115(3) . . ?
C4B C3B C2B 111(2) . . ?
C8C C7C C6 129.8(17) . . ?
C8C C7C S2C 112.4(10) . . ?
C6 C7C S2C 117.7(13) . . ?
C7C C8C C9C 109.9(16) . . ?
C10C C9C C8C 114.1(14) . . ?
C9C C10C S2C 111.9(13) . . ?
C10C S2C C7C 91.4(7) . . ?
C8D C7D C6 122(4) . . ?
C8D C7D S2D 111.0(19) . . ?
C6 C7D S2D 124(3) . . ?
C10D S2D C7D 95.4(15) . . ?
C9D C10D S2D 108(3) . . ?
C10D C9D C8D 115(3) . . ?
C7D C8D C9D 109(2) . . ?
C6 C5 C4A 132(3) . . ?
C6 C5 C4B 133(5) . . ?
C6 C5 C25 93.2(4) . . ?
C4A C5 C25 135(3) . . ?
C4B C5 C25 134(5) . . ?
C5 C6 C7C 129.5(13) . . ?
C5 C6 C7D 128(3) . . ?
C5 C6 C11 92.6(4) . . ?
C7C C6 C11 137.6(12) . . ?
C7D C6 C11 139(3) . . ?
C12 C11 C6 134.1(4) . . ?
C12 C11 C25 138.5(4) . . ?
C6 C11 C25 86.7(3) . . ?
C11 C12 C19 124.2(4) . . ?
C11 C12 C13 120.2(4) . . ?
C19 C12 C13 115.6(3) . . ?
C14 C13 C18 120.0 . . ?
C14 C13 C12 119.9(2) . . ?
C18 C13 C12 120.0(2) . . ?
C13 C14 C15 120.0 . . ?
C16 C15 C14 120.0 . . ?
C15 C16 C17 120.0 . . ?
C18 C17 C16 120.0 . . ?
C17 C18 C13 120.0 . . ?
C20 C19 C24 120.0 . . ?
C20 C19 C12 118.4(2) . . ?
C24 C19 C12 121.5(2) . . ?
C21 C20 C19 120.0 . . ?
C20 C21 C22 120.0 . . ?
C23 C22 C21 120.0 . . ?
C24 C23 C22 120.0 . . ?
C23 C24 C19 120.0 . . ?
C26 C25 C5 132.1(4) . . ?
C26 C25 C11 139.9(4) . . ?
C5 C25 C11 87.3(3) . . ?
C25 C26 C27 124.5(4) . . ?
C25 C26 C33 119.6(4) . . ?
C27 C26 C33 115.9(3) . . ?
C28 C27 C32 120.0 . . ?
C28 C27 C26 123.4(2) . . ?
C32 C27 C26 116.6(2) . . ?
C27 C28 C29 120.0 . . ?
C28 C29 C30 120.0 . . ?
C31 C30 C29 120.0 . . ?
C32 C31 C30 120.0 . . ?
C31 C32 C27 120.0 . . ?
C34 C33 C38 120.0 . . ?
C34 C33 C26 120.4(2) . . ?
C38 C33 C26 119.5(2) . . ?
C35 C34 C33 120.0 . . ?
C34 C35 C36 120.0 . . ?
C37 C36 C35 120.0 . . ?
C38 C37 C36 120.0 . . ?
C37 C38 C33 120.0 . . ?

_refine_diff_density_max         0.265
_refine_diff_density_min         -0.250
_refine_diff_density_rms         0.038

_shelxl_version_number           2013-3
_database_code_depnum_ccdc_archive 'CCDC 970529'
#######################################################################
#
#                 Cambridge Crystallographic Data Centre
#                                CCDC 
# 
#######################################################################
# 
#  This CIF contains data from an original supplementary publication
#  deposited with the CCDC, and may include chemical, crystal,
#  experimental, refinement, atomic coordinates,
#  anisotropic displacement parameters and molecular geometry data,
#  as required by the journal to which it was submitted.
#
#  This CIF is provided on the understanding that it is used for bona
#  fide research purposes only. It may contain copyright material
#  of the CCDC or of third parties, and may not be copied or further
#  disseminated in any form, whether machine-readable or not,
#  except for the purpose of generating routine backup copies
#  on your local computer system.
# 
#  For further information on the CCDC, data deposition and
#  data retrieval see:
#                         www.ccdc.cam.ac.uk
#
#  Bona fide researchers may freely download Mercury and enCIFer
#  from this site to visualise CIF-encoded structures and 
#  to carry out CIF format checking respectively.
#
data_Compound_2a

_audit_creation_method           
'SHELXL-2012 & Rigaku CrystalClear-SM Expert 2.0 r4'

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'

_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                   15.0983(3)
_cell_length_b                   7.1706(2)
_cell_length_c                   14.2489(5)
_cell_angle_alpha                90
_cell_angle_beta                 100.6160(10)
_cell_angle_gamma                90
_cell_volume                     1516.24(7)
_cell_formula_units_Z            2
_cell_measurement_temperature    153(2)
_cell_measurement_reflns_used    5264
_cell_measurement_theta_min      1.4
_cell_measurement_theta_max      27.5

_exptl_crystal_description       Prism
_exptl_crystal_colour            Red
_exptl_crystal_size_max          0.25
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.12
_chemical_formula_weight         622.68
_chemical_formula_analytical     ?
_chemical_formula_sum            'C42 H26 N2 O4 '
_exptl_absorpt_coefficient_mu    0.088
_exptl_absorpt_correction_type   Numerical
_exptl_absorpt_correction_T_max  0.991
_exptl_absorpt_correction_T_min  0.984
_exptl_crystal_F_000             648
_exptl_absorpt_process_details   'CrystalClear-SM Expert 2.0 r4 (Rigaku, 2009)'

_exptl_special_details           
;
 ?
;
_diffrn_source_power             1.8
_diffrn_source_voltage           50.0
_diffrn_source_current           35.0
_diffrn_radiation_wavelength     0.71075
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  'Graphite Monochromator'
_diffrn_measurement_device       'Crystal Goniometer'
_diffrn_measurement_device_type  'Rigaku RAXIS II'
_diffrn_measurement_specimen_support Fiber
_diffrn_detector                 'Curved image plate'
_diffrn_measurement_method       'profile data from ω-scans'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_ambient_temperature      153(2)
_diffrn_reflns_number            14425
_diffrn_reflns_av_unetI/netI     0.0784
_diffrn_reflns_av_R_equivalents  0.0759
_diffrn_reflns_limit_h_min       -19
_diffrn_reflns_limit_h_max       19
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_theta_min         2.909
_diffrn_reflns_theta_max         27.507
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measured_fraction_theta_full 0.995
_diffrn_reflns_Laue_measured_fraction_max 0.995
_diffrn_reflns_Laue_measured_fraction_full 0.995
_diffrn_reflns_point_group_measured_fraction_max 0.995
_diffrn_reflns_point_group_measured_fraction_full 0.995
_reflns_number_total             3475
_reflns_number_gt                2771
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .
_diffrn_measurement_details      
;
scan:
	Number of images: 50
	           Slice: 20.0000 - 170.0000
	     Image width: 3.0000
	        Exp time: 180.0000
	   Rotation axis: Omega
	           Omega: 0.0000
	             Chi: 30.0000
	             Phi: 0.0000
	             XTD: 127.4000
	          2theta: -0.0234
scan:
	Number of images: 25
	           Slice: 95.0000 - 170.0000
	     Image width: 3.0000
	        Exp time: 180.0000
	   Rotation axis: Omega
	           Omega: 0.0000
	             Chi: 45.0000
	             Phi: 0.0000
	             XTD: 127.4000
	          2theta: -0.0234
;
_diffrn_orient_matrix_UB_11      0.066123
_diffrn_orient_matrix_UB_12      -0.011485
_diffrn_orient_matrix_UB_13      0.024378
_diffrn_orient_matrix_UB_21      0.010597
_diffrn_orient_matrix_UB_22      0.134657
_diffrn_orient_matrix_UB_23      0.034698
_diffrn_orient_matrix_UB_31      -0.012988
_diffrn_orient_matrix_UB_32      -0.015539
_diffrn_orient_matrix_UB_33      0.064271
_diffrn_orient_matrix_type       d*Trek

_computing_data_collection       
;
CrystalClear-SM Expert 2.0 r4 (Rigaku, 2009)
;
_computing_cell_refinement       
;
CrystalClear-SM Expert 2.0 r4 (Rigaku, 2009)
;
_computing_data_reduction        
;
CrystalClear-SM Expert 2.0 r4 (Rigaku, 2009)
;
_computing_structure_solution    'SHELXS-2013 (Sheldrick, 2013)'
_computing_structure_refinement  'SHELXL-2013 (Sheldrick, 2013)'
_computing_molecular_graphics    ?
_computing_publication_material  ?

_refine_special_details          
;
'Refinement of F² against ALL reflections.  The weighted R-factor wR and
 goodness of fit S are based on F², conventional R-factors R are based
 on F, with F set to zero for negative F². The threshold expression of
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is
 not relevant to the choice of reflections for refinement.  R-factors based
 on F² are statistically about twice as large as those based on F, and R-
 factors based on ALL data will be even larger.'
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0374P)²+1.1252P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     SHELXL
_refine_ls_extinction_coef       0.025(3)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         3475
_refine_ls_number_parameters     188
_refine_ls_number_restraints     180
_refine_ls_R_factor_all          0.0853
_refine_ls_R_factor_gt           0.0673
_refine_ls_wR_factor_ref         0.1543
_refine_ls_wR_factor_gt          0.1439
_refine_ls_goodness_of_fit_ref   1.068
_refine_ls_restrained_S_all      1.047
_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
C1 C 0.19529(5) 1.14297(13) 0.97104(6) 0.0262(4) Uani 1 1 d G U . . .
C2 C 0.25861(7) 1.24832(10) 1.03195(6) 0.0325(5) Uani 1 1 d G U . . .
H2 H 0.2404 1.3229 1.0801 0.039 Uiso 1 1 calc R U . . .
C3 C 0.34855(6) 1.24458(13) 1.02233(7) 0.0405(6) Uani 1 1 d G U . . .
H3 H 0.3918 1.3166 1.0640 0.049 Uiso 1 1 calc R U . . .
C4 C 0.37518(6) 1.13549(17) 0.95181(7) 0.0432(6) Uani 1 1 d G U . . .
H4 H 0.4366 1.1329 0.9452 0.052 Uiso 1 1 calc R U . . .
C5 C 0.31186(7) 1.03014(17) 0.89090(5) 0.0402(6) Uani 1 1 d G U . . .
H5 H 0.3301 0.9556 0.8427 0.048 Uiso 1 1 calc R U . . .
C6 C 0.22192(6) 1.03388(15) 0.90052(5) 0.0320(5) Uani 1 1 d G U . . .
H6 H 0.1786 0.9619 0.8589 0.038 Uiso 1 1 calc R U . . .
C7 C 0.19385(5) 0.87770(13) 1.11751(6) 0.0248(4) Uani 1 1 d G U . . .
C8 C 0.21080(6) 0.98589(15) 1.19981(5) 0.0299(5) Uani 1 1 d G U . . .
H8 H 0.1629 1.0508 1.2202 0.036 Uiso 1 1 calc R U . . .
C9 C 0.29784(7) 0.99904(16) 1.25222(5) 0.0329(5) Uani 1 1 d G U . . .
H9 H 0.3094 1.0730 1.3085 0.040 Uiso 1 1 calc R U . . .
C10 C 0.36794(6) 0.90400(16) 1.22232(6) 0.0314(5) Uani 1 1 d G U . . .
C11 C 0.35099(6) 0.79580(12) 1.14002(7) 0.0328(5) Uani 1 1 d G U . . .
H11 H 0.3989 0.7308 1.1196 0.039 Uiso 1 1 calc R U . . .
C12 C 0.26395(6) 0.78265(9) 1.08761(6) 0.0295(5) Uani 1 1 d G U . . .
H12 H 0.2524 0.7087 1.0314 0.035 Uiso 1 1 calc R U . . .
C13 C 0.09515(12) 1.1510(3) 0.97373(14) 0.0241(4) Uani 1 1 d . U . . .
C14 C 0.04961(12) 1.0027(3) 1.01090(14) 0.0234(4) Uani 1 1 d . U . . .
C15 C 0.09629(12) 0.8587(3) 1.06942(14) 0.0244(4) Uani 1 1 d . U . . .
C16 C 0.05024(13) 0.7055(3) 1.09680(13) 0.0242(4) Uani 1 1 d . U . . .
C17 C 0.09599(14) 0.5576(3) 1.15502(14) 0.0287(5) Uani 1 1 d . U . . .
H17 H 0.1598 0.5615 1.1730 0.034 Uiso 1 1 calc R U . . .
C18 C 0.05029(14) 0.4128(3) 1.18485(15) 0.0314(5) Uani 1 1 d . U . . .
H18 H 0.0824 0.3169 1.2226 0.038 Uiso 1 1 calc R U . . .
C19 C -0.04490(15) 0.4037(3) 1.16015(15) 0.0315(5) Uani 1 1 d . U . . .
H19 H -0.0762 0.3006 1.1804 0.038 Uiso 1 1 calc R U . . .
C20 C -0.09152(14) 0.5422(3) 1.10753(14) 0.0287(5) Uani 1 1 d . U . . .
H20 H -0.1554 0.5351 1.0925 0.034 Uiso 1 1 calc R U . . .
C21 C -0.04691(13) 0.6988(3) 1.07414(14) 0.0249(4) Uani 1 1 d . U . . .
N N 0.45827(12) 0.9208(3) 1.27714(15) 0.0402(5) Uani 1 1 d . U . . .
O O 0.46717(11) 0.9789(3) 1.35921(13) 0.0516(5) Uani 1 1 d . U . . .
O1 O 0.52149(11) 0.8755(4) 1.23951(15) 0.0633(7) Uani 1 1 d . 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
C1 C2 1.3900 . ?
C1 C6 1.3900 . ?
C1 C13 1.521(2) . ?
C2 C3 1.3900 . ?
C3 C4 1.3900 . ?
C4 C5 1.3900 . ?
C5 C6 1.3900 . ?
C7 C8 1.3900 . ?
C7 C12 1.3900 . ?
C7 C15 1.5120(19) . ?
C8 C9 1.3900 . ?
C9 C10 1.3900 . ?
C10 C11 1.3900 . ?
C10 N 1.4464(19) . ?
C11 C12 1.3900 . ?
C13 C21 1.404(3) 3_577 ?
C13 C14 1.421(3) . ?
C14 C15 1.429(3) . ?
C14 C14 1.473(4) 3_577 ?
C15 C16 1.394(3) . ?
C16 C17 1.442(3) . ?
C16 C21 1.443(3) . ?
C17 C18 1.357(3) . ?
C18 C19 1.417(3) . ?
C19 C20 1.360(3) . ?
C20 C21 1.435(3) . ?
C21 C13 1.404(3) 3_577 ?
N O1 1.222(3) . ?
N O 1.225(3) . ?

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 120.0 . . ?
C2 C1 C13 122.43(9) . . ?
C6 C1 C13 117.45(9) . . ?
C3 C2 C1 120.0 . . ?
C2 C3 C4 120.0 . . ?
C5 C4 C3 120.0 . . ?
C4 C5 C6 120.0 . . ?
C5 C6 C1 120.0 . . ?
C8 C7 C12 120.0 . . ?
C8 C7 C15 116.43(9) . . ?
C12 C7 C15 123.39(9) . . ?
C7 C8 C9 120.0 . . ?
C10 C9 C8 120.0 . . ?
C9 C10 C11 120.0 . . ?
C9 C10 N 119.28(11) . . ?
C11 C10 N 120.72(11) . . ?
C12 C11 C10 120.0 . . ?
C11 C12 C7 120.0 . . ?
C21 C13 C14 120.77(17) 3_577 . ?
C21 C13 C1 116.49(16) 3_577 . ?
C14 C13 C1 122.19(16) . . ?
C13 C14 C15 122.54(17) . . ?
C13 C14 C14 119.0(2) . 3_577 ?
C15 C14 C14 118.5(2) . 3_577 ?
C16 C15 C14 121.01(17) . . ?
C16 C15 C7 116.01(15) . . ?
C14 C15 C7 122.29(16) . . ?
C15 C16 C17 122.02(18) . . ?
C15 C16 C21 120.15(17) . . ?
C17 C16 C21 117.61(18) . . ?
C18 C17 C16 121.69(19) . . ?
C17 C18 C19 120.58(19) . . ?
C20 C19 C18 120.1(2) . . ?
C19 C20 C21 121.83(19) . . ?
C13 C21 C20 121.86(18) 3_577 . ?
C13 C21 C16 119.86(18) 3_577 . ?
C20 C21 C16 118.14(18) . . ?
O1 N O 123.51(19) . . ?
O1 N C10 118.43(18) . . ?
O N C10 118.06(18) . . ?

_refine_diff_density_max         0.408
_refine_diff_density_min         -0.267
_refine_diff_density_rms         0.056

_shelxl_version_number           2013-3
_database_code_depnum_ccdc_archive 'CCDC 970530'
