# Electronic Supplementary Material (ESI) for Journal of Materials Chemistry C.
# This journal is © The Royal Society of Chemistry 2015

####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_a
_database_code_depnum_ccdc_archive 'CCDC 1415294'
_audit_update_record             
;
2015-07-26 deposited with the CCDC.
2015-09-08 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C22 H14'
_chemical_formula_weight         278.33

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           Triclinic
_symmetry_space_group_name_H-M   'P-1   '

loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   6.055(3)
_cell_length_b                   9.804(4)
_cell_length_c                   13.814(2)
_cell_angle_alpha                90.34
_cell_angle_beta                 94.20
_cell_angle_gamma                103.93
_cell_volume                     793.5(5)
_cell_formula_units_Z            2
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    660
_cell_measurement_theta_min      2.96
_cell_measurement_theta_max      23.16

_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.26
_exptl_crystal_size_mid          0.21
_exptl_crystal_size_min          0.17
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.165
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             292
_exptl_absorpt_coefficient_mu    0.066
_exptl_absorpt_correction_type   Multi-scan
_exptl_absorpt_correction_T_min  0.9831
_exptl_absorpt_correction_T_max  0.9889
_exptl_absorpt_process_details   SADABS

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            4003
_diffrn_reflns_av_R_equivalents  0.0208
_diffrn_reflns_av_sigmaI/netI    0.0438
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_theta_min         2.14
_diffrn_reflns_theta_max         25.00
_reflns_number_total             2761
_reflns_number_gt                1239
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'

_refine_special_details          
; 
 Refinement of F² against ALL reflections.  The weighted R-factor wR and 
 goodness of fit S are based on F², conventional R-factors R are based 
 on F, with F set to zero for negative F². The threshold expression of 
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is 
 not relevant to the choice of reflections for refinement.  R-factors based 
 on F² are statistically about twice as large as those based on F, and R- 
 factors based on ALL data will be even larger. 
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0365P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         2761
_refine_ls_number_parameters     199
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1232
_refine_ls_R_factor_gt           0.0494
_refine_ls_wR_factor_ref         0.1090
_refine_ls_wR_factor_gt          0.0931
_refine_ls_goodness_of_fit_ref   1.015
_refine_ls_restrained_S_all      1.015
_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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 0.5056(4) 0.7534(2) 0.13391(17) 0.0719(7) Uani 1 1 d . . .
H1 H 0.3518 0.7213 0.1135 0.086 Uiso 1 1 calc R . .
C2 C 0.6616(5) 0.8105(2) 0.06791(16) 0.0841(8) Uani 1 1 d . . .
H2 H 0.6124 0.8171 0.0031 0.101 Uiso 1 1 calc R . .
C3 C 0.8891(5) 0.8577(2) 0.09787(19) 0.0812(8) Uani 1 1 d . . .
H3 H 0.9937 0.8950 0.0532 0.097 Uiso 1 1 calc R . .
C4 C 0.9616(4) 0.8498(2) 0.19318(19) 0.0743(7) Uani 1 1 d . . .
H4 H 1.1156 0.8819 0.2132 0.089 Uiso 1 1 calc R . .
C5 C 0.8083(4) 0.7945(2) 0.25980(15) 0.0636(6) Uani 1 1 d . . .
H5 H 0.8588 0.7910 0.3247 0.076 Uiso 1 1 calc R . .
C6 C 0.5794(4) 0.7441(2) 0.23082(15) 0.0567(6) Uani 1 1 d . . .
C7 C 0.4235(4) 0.6809(2) 0.30061(15) 0.0630(6) Uani 1 1 d . . .
C8 C 0.2990(4) 0.6252(2) 0.35944(15) 0.0607(6) Uani 1 1 d . . .
C9 C 0.1484(4) 0.5611(2) 0.43064(15) 0.0536(5) Uani 1 1 d . . .
C10 C 0.2287(4) 0.55242(19) 0.52663(16) 0.0600(6) Uani 1 1 d . . .
H10 H 0.3831 0.5872 0.5450 0.072 Uiso 1 1 calc R . .
C11 C -0.0827(4) 0.5070(2) 0.40510(14) 0.0605(6) Uani 1 1 d . . .
H11 H -0.1393 0.5110 0.3410 0.073 Uiso 1 1 calc R . .
C12 C 0.5704(4) 0.3675(2) 0.18689(14) 0.0628(6) Uani 1 1 d . . .
H12 H 0.4549 0.4110 0.2000 0.075 Uiso 1 1 calc R . .
C13 C 0.7303(4) 0.4276(2) 0.12456(15) 0.0735(7) Uani 1 1 d . . .
H13 H 0.7220 0.5117 0.0954 0.088 Uiso 1 1 calc R . .
C14 C 0.9018(4) 0.3655(3) 0.10475(16) 0.0803(7) Uani 1 1 d . . .
H14 H 1.0115 0.4079 0.0634 0.096 Uiso 1 1 calc R . .
C15 C 0.9106(4) 0.2398(2) 0.14640(16) 0.0788(7) Uani 1 1 d . . .
H15 H 1.0253 0.1963 0.1321 0.095 Uiso 1 1 calc R . .
C16 C 0.7520(4) 0.1779(2) 0.20879(14) 0.0665(6) Uani 1 1 d . . .
H16 H 0.7597 0.0929 0.2366 0.080 Uiso 1 1 calc R . .
C17 C 0.5809(4) 0.2414(2) 0.23051(14) 0.0548(6) Uani 1 1 d . . .
C18 C 0.4225(4) 0.1793(2) 0.29980(15) 0.0605(6) Uani 1 1 d . . .
C19 C 0.2998(4) 0.1276(2) 0.36065(15) 0.0604(6) Uani 1 1 d . . .
C20 C 0.1492(4) 0.0641(2) 0.43183(14) 0.0530(5) Uani 1 1 d . . .
C21 C -0.0288(4) 0.1208(2) 0.45596(14) 0.0607(6) Uani 1 1 d . . .
H21 H -0.0491 0.2024 0.4265 0.073 Uiso 1 1 calc R . .
C22 C 0.1757(3) -0.0581(2) 0.47722(14) 0.0594(6) Uani 1 1 d . . .
H22 H 0.2943 -0.0976 0.4621 0.071 Uiso 1 1 calc R . .


_geom_special_details            
; 
 All esds (except the esd in the dihedral angle between two l.s. planes) 
 are estimated using the full covariance matrix.  The cell esds are taken 
 into account individually in the estimation of esds in distances, angles 
 and torsion angles; correlations between esds in cell parameters are only 
 used when they are defined by crystal symmetry.  An approximate (isotropic) 
 treatment of cell esds is used for estimating esds involving l.s. planes. 
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C1 C2 1.384(3) . ?
C1 C6 1.390(3) . ?
C1 H1 0.9300 . ?
C2 C3 1.375(3) . ?
C2 H2 0.9300 . ?
C3 C4 1.366(3) . ?
C3 H3 0.9300 . ?
C4 C5 1.375(3) . ?
C4 H4 0.9300 . ?
C5 C6 1.383(3) . ?
C5 H5 0.9300 . ?
C6 C7 1.436(3) . ?
C7 C8 1.193(2) . ?
C8 C9 1.434(3) . ?
C9 C10 1.389(2) . ?
C9 C11 1.390(3) . ?
C10 C11 1.375(3) 2_566 ?
C10 H10 0.9300 . ?
C11 C10 1.375(3) 2_566 ?
C11 H11 0.9300 . ?
C12 C13 1.371(3) . ?
C12 C17 1.392(2) . ?
C12 H12 0.9300 . ?
C13 C14 1.367(3) . ?
C13 H13 0.9300 . ?
C14 C15 1.374(3) . ?
C14 H14 0.9300 . ?
C15 C16 1.371(3) . ?
C15 H15 0.9300 . ?
C16 C17 1.380(3) . ?
C16 H16 0.9300 . ?
C17 C18 1.438(3) . ?
C18 C19 1.196(2) . ?
C19 C20 1.432(3) . ?
C20 C21 1.386(2) . ?
C20 C22 1.393(2) . ?
C21 C22 1.373(3) 2_556 ?
C21 H21 0.9300 . ?
C22 C21 1.373(3) 2_556 ?
C22 H22 0.9300 . ?

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 119.8(2) . . ?
C2 C1 H1 120.1 . . ?
C6 C1 H1 120.1 . . ?
C3 C2 C1 120.2(2) . . ?
C3 C2 H2 119.9 . . ?
C1 C2 H2 119.9 . . ?
C4 C3 C2 120.1(2) . . ?
C4 C3 H3 120.0 . . ?
C2 C3 H3 120.0 . . ?
C3 C4 C5 120.4(2) . . ?
C3 C4 H4 119.8 . . ?
C5 C4 H4 119.8 . . ?
C4 C5 C6 120.4(2) . . ?
C4 C5 H5 119.8 . . ?
C6 C5 H5 119.8 . . ?
C5 C6 C1 119.1(2) . . ?
C5 C6 C7 119.6(2) . . ?
C1 C6 C7 121.3(2) . . ?
C8 C7 C6 177.6(2) . . ?
C7 C8 C9 178.7(2) . . ?
C10 C9 C11 118.36(19) . . ?
C10 C9 C8 121.1(2) . . ?
C11 C9 C8 120.6(2) . . ?
C11 C10 C9 120.8(2) 2_566 . ?
C11 C10 H10 119.6 2_566 . ?
C9 C10 H10 119.6 . . ?
C10 C11 C9 120.8(2) 2_566 . ?
C10 C11 H11 119.6 2_566 . ?
C9 C11 H11 119.6 . . ?
C13 C12 C17 120.0(2) . . ?
C13 C12 H12 120.0 . . ?
C17 C12 H12 120.0 . . ?
C14 C13 C12 120.8(2) . . ?
C14 C13 H13 119.6 . . ?
C12 C13 H13 119.6 . . ?
C13 C14 C15 119.4(2) . . ?
C13 C14 H14 120.3 . . ?
C15 C14 H14 120.3 . . ?
C16 C15 C14 120.7(2) . . ?
C16 C15 H15 119.7 . . ?
C14 C15 H15 119.7 . . ?
C15 C16 C17 120.3(2) . . ?
C15 C16 H16 119.9 . . ?
C17 C16 H16 119.9 . . ?
C16 C17 C12 118.90(19) . . ?
C16 C17 C18 119.8(2) . . ?
C12 C17 C18 121.3(2) . . ?
C19 C18 C17 176.7(2) . . ?
C18 C19 C20 178.7(2) . . ?
C21 C20 C22 118.33(18) . . ?
C21 C20 C19 121.0(2) . . ?
C22 C20 C19 120.6(2) . . ?
C22 C21 C20 120.88(19) 2_556 . ?
C22 C21 H21 119.6 2_556 . ?
C20 C21 H21 119.6 . . ?
C21 C22 C20 120.79(19) 2_556 . ?
C21 C22 H22 119.6 2_556 . ?
C20 C22 H22 119.6 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C6 C1 C2 C3 0.2(3) . . . . ?
C1 C2 C3 C4 -0.8(3) . . . . ?
C2 C3 C4 C5 0.1(3) . . . . ?
C3 C4 C5 C6 1.1(3) . . . . ?
C4 C5 C6 C1 -1.6(3) . . . . ?
C4 C5 C6 C7 177.13(18) . . . . ?
C2 C1 C6 C5 1.0(3) . . . . ?
C2 C1 C6 C7 -177.74(18) . . . . ?
C5 C6 C7 C8 -54(6) . . . . ?
C1 C6 C7 C8 125(5) . . . . ?
C6 C7 C8 C9 144(9) . . . . ?
C7 C8 C9 C10 -90(11) . . . . ?
C7 C8 C9 C11 90(11) . . . . ?
C11 C9 C10 C11 -0.7(3) . . . 2_566 ?
C8 C9 C10 C11 178.86(17) . . . 2_566 ?
C10 C9 C11 C10 0.7(3) . . . 2_566 ?
C8 C9 C11 C10 -178.86(17) . . . 2_566 ?
C17 C12 C13 C14 -0.3(3) . . . . ?
C12 C13 C14 C15 1.3(3) . . . . ?
C13 C14 C15 C16 -1.2(3) . . . . ?
C14 C15 C16 C17 0.0(3) . . . . ?
C15 C16 C17 C12 1.0(3) . . . . ?
C15 C16 C17 C18 -176.8(2) . . . . ?
C13 C12 C17 C16 -0.9(3) . . . . ?
C13 C12 C17 C18 176.9(2) . . . . ?
C16 C17 C18 C19 53(4) . . . . ?
C12 C17 C18 C19 -125(3) . . . . ?
C17 C18 C19 C20 -149(9) . . . . ?
C18 C19 C20 C21 -82(10) . . . . ?
C18 C19 C20 C22 97(10) . . . . ?
C22 C20 C21 C22 -0.1(3) . . . 2_556 ?
C19 C20 C21 C22 178.68(19) . . . 2_556 ?
C21 C20 C22 C21 0.1(3) . . . 2_556 ?
C19 C20 C22 C21 -178.68(19) . . . 2_556 ?

_diffrn_measured_fraction_theta_max 0.987
_diffrn_reflns_theta_full        25.00
_diffrn_measured_fraction_theta_full 0.987
_refine_diff_density_max         0.111
_refine_diff_density_min         -0.121
_refine_diff_density_rms         0.029
####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_a
_database_code_depnum_ccdc_archive 'CCDC 1415295'
_audit_update_record             
;
2015-07-26 deposited with the CCDC.
2015-09-08 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C46 H62 B4 O8'
_chemical_formula_weight         786.20

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'
B B 0.0013 0.0007 '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'

_symmetry_cell_setting           Monoclinic
_symmetry_space_group_name_H-M   'P2(1)/c  '

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

_cell_length_a                   6.668(2)
_cell_length_b                   11.794(3)
_cell_length_c                   28.968(9)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.446(5)
_cell_angle_gamma                90.00
_cell_volume                     2278.1(12)
_cell_formula_units_Z            2
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    3520
_cell_measurement_theta_min      2.73
_cell_measurement_theta_max      24.61

_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.26
_exptl_crystal_size_mid          0.24
_exptl_crystal_size_min          0.21
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.146
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             844
_exptl_absorpt_coefficient_mu    0.075
_exptl_absorpt_correction_type   Multi-scan
_exptl_absorpt_correction_T_min  0.9808
_exptl_absorpt_correction_T_max  0.9844
_exptl_absorpt_process_details   SADABS

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      296(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            11265
_diffrn_reflns_av_R_equivalents  0.0220
_diffrn_reflns_av_sigmaI/netI    0.0240
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_l_min       -34
_diffrn_reflns_limit_l_max       34
_diffrn_reflns_theta_min         1.86
_diffrn_reflns_theta_max         25.00
_reflns_number_total             3976
_reflns_number_gt                2880
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'

_refine_special_details          
; 
 Refinement of F² against ALL reflections.  The weighted R-factor wR and 
 goodness of fit S are based on F², conventional R-factors R are based 
 on F, with F set to zero for negative F². The threshold expression of 
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is 
 not relevant to the choice of reflections for refinement.  R-factors based 
 on F² are statistically about twice as large as those based on F, and R- 
 factors based on ALL data will be even larger. 
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0500P)²+2.6000P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         3976
_refine_ls_number_parameters     270
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1003
_refine_ls_R_factor_gt           0.0757
_refine_ls_wR_factor_ref         0.1804
_refine_ls_wR_factor_gt          0.1694
_refine_ls_goodness_of_fit_ref   1.056
_refine_ls_restrained_S_all      1.056
_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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
B1 B 0.7160(5) 0.3118(3) 0.09124(10) 0.0443(7) Uani 1 1 d . . .
B2 B 0.5364(5) 0.4085(3) 0.17850(10) 0.0447(7) Uani 1 1 d . . .
C1 C 0.1411(5) 0.5376(3) 0.14199(10) 0.0547(8) Uani 1 1 d . . .
H1 H 0.1052 0.4681 0.1546 0.066 Uiso 1 1 calc R . .
C2 C -0.0008(6) 0.6218(3) 0.13783(13) 0.0734(10) Uani 1 1 d . . .
H2 H -0.1319 0.6085 0.1471 0.088 Uiso 1 1 calc R . .
C3 C 0.0507(7) 0.7243(3) 0.12012(14) 0.0816(12) Uani 1 1 d . . .
H3 H -0.0453 0.7811 0.1172 0.098 Uiso 1 1 calc R . .
C4 C 0.2445(7) 0.7441(3) 0.10646(12) 0.0732(11) Uani 1 1 d . . .
H4 H 0.2799 0.8145 0.0946 0.088 Uiso 1 1 calc R . .
C5 C 0.3871(5) 0.6593(3) 0.11031(10) 0.0582(8) Uani 1 1 d . . .
H5 H 0.5181 0.6731 0.1011 0.070 Uiso 1 1 calc R . .
C6 C 0.3362(4) 0.5546(2) 0.12774(8) 0.0447(7) Uani 1 1 d . . .
C7 C 0.4843(4) 0.4596(2) 0.13048(9) 0.0430(6) Uani 1 1 d . . .
C8 C 0.5767(4) 0.4192(2) 0.09267(8) 0.0410(6) Uani 1 1 d . . .
C9 C 0.5353(4) 0.4625(2) 0.04514(8) 0.0399(6) Uani 1 1 d . . .
C10 C 0.6923(4) 0.4946(2) 0.01701(9) 0.0448(7) Uani 1 1 d . . .
H10 H 0.8231 0.4906 0.0283 0.054 Uiso 1 1 calc R . .
C11 C 0.3418(4) 0.4677(2) 0.02729(9) 0.0439(6) Uani 1 1 d . . .
H11 H 0.2342 0.4455 0.0454 0.053 Uiso 1 1 calc R . .
C12 C 0.7866(5) 0.1326(3) 0.07152(14) 0.0726(10) Uani 1 1 d . . .
C13 C 0.7686(10) 0.0191(4) 0.0907(3) 0.185(4) Uani 1 1 d . . .
H13A H 0.7847 0.0224 0.1237 0.278 Uiso 1 1 calc R . .
H13B H 0.8704 -0.0289 0.0780 0.278 Uiso 1 1 calc R . .
H13C H 0.6387 -0.0112 0.0833 0.278 Uiso 1 1 calc R . .
C14 C 0.7334(8) 0.1290(5) 0.01893(18) 0.132(2) Uani 1 1 d . . .
H14A H 0.5932 0.1130 0.0150 0.198 Uiso 1 1 calc R . .
H14B H 0.8107 0.0708 0.0042 0.198 Uiso 1 1 calc R . .
H14C H 0.7637 0.2010 0.0052 0.198 Uiso 1 1 calc R . .
C15 C 0.9816(5) 0.1966(3) 0.07875(13) 0.0686(10) Uani 1 1 d . . .
C16 C 1.0823(10) 0.1711(5) 0.1252(2) 0.160(3) Uani 1 1 d . . .
H16A H 1.1518 0.2375 0.1360 0.240 Uiso 1 1 calc R . .
H16B H 1.1762 0.1101 0.1216 0.240 Uiso 1 1 calc R . .
H16C H 0.9823 0.1498 0.1473 0.240 Uiso 1 1 calc R . .
C17 C 1.1376(7) 0.1866(4) 0.0430(2) 0.1167(18) Uani 1 1 d . . .
H17A H 1.0840 0.2110 0.0138 0.175 Uiso 1 1 calc R . .
H17B H 1.1800 0.1090 0.0408 0.175 Uiso 1 1 calc R . .
H17C H 1.2502 0.2333 0.0513 0.175 Uiso 1 1 calc R . .
C18 C 0.7179(7) 0.3263(4) 0.23571(12) 0.0827(12) Uani 1 1 d . . .
C19 C 0.8031(7) 0.2122(3) 0.24545(14) 0.0880(13) Uani 1 1 d . . .
H19A H 0.7233 0.1555 0.2302 0.132 Uiso 1 1 calc R . .
H19B H 0.8027 0.1987 0.2781 0.132 Uiso 1 1 calc R . .
H19C H 0.9382 0.2086 0.2343 0.132 Uiso 1 1 calc R . .
C20 C 0.8633(7) 0.4236(4) 0.25366(16) 0.1084(16) Uani 1 1 d . . .
H20A H 0.9819 0.4250 0.2351 0.163 Uiso 1 1 calc R . .
H20B H 0.8997 0.4092 0.2853 0.163 Uiso 1 1 calc R . .
H20C H 0.7962 0.4954 0.2515 0.163 Uiso 1 1 calc R . .
C21 C 0.5177(8) 0.3524(5) 0.25259(13) 0.1030(17) Uani 1 1 d . . .
C22 C 0.3872(7) 0.2361(5) 0.2495(2) 0.138(2) Uani 1 1 d . . .
H22A H 0.4167 0.1975 0.2212 0.207 Uiso 1 1 calc R . .
H22B H 0.2469 0.2541 0.2504 0.207 Uiso 1 1 calc R . .
H22C H 0.4209 0.1881 0.2752 0.207 Uiso 1 1 calc R . .
C23 C 0.4860(8) 0.4080(5) 0.29801(12) 0.129(2) Uani 1 1 d . . .
H23A H 0.5269 0.3575 0.3223 0.194 Uiso 1 1 calc R . .
H23B H 0.3465 0.4261 0.3014 0.194 Uiso 1 1 calc R . .
H23C H 0.5640 0.4763 0.2997 0.194 Uiso 1 1 calc R . .
O1 O 0.6371(3) 0.20698(18) 0.09043(9) 0.0682(7) Uani 1 1 d . . .
O2 O 0.9149(3) 0.31349(17) 0.08198(8) 0.0625(6) Uani 1 1 d . . .
O3 O 0.6937(4) 0.3408(2) 0.18587(7) 0.0863(9) Uani 1 1 d . . .
O4 O 0.4359(4) 0.4290(3) 0.21704(7) 0.0957(10) Uani 1 1 d . . .


_geom_special_details            
; 
 All esds (except the esd in the dihedral angle between two l.s. planes) 
 are estimated using the full covariance matrix.  The cell esds are taken 
 into account individually in the estimation of esds in distances, angles 
 and torsion angles; correlations between esds in cell parameters are only 
 used when they are defined by crystal symmetry.  An approximate (isotropic) 
 treatment of cell esds is used for estimating esds involving l.s. planes. 
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
B1 O1 1.344(4) . ?
B1 O2 1.355(4) . ?
B1 C8 1.572(4) . ?
B2 O4 1.329(4) . ?
B2 O3 1.334(4) . ?
B2 C7 1.553(4) . ?
C1 C2 1.376(4) . ?
C1 C6 1.382(4) . ?
C1 H1 0.9300 . ?
C2 C3 1.358(6) . ?
C2 H2 0.9300 . ?
C3 C4 1.375(6) . ?
C3 H3 0.9300 . ?
C4 C5 1.384(5) . ?
C4 H4 0.9300 . ?
C5 C6 1.377(4) . ?
C5 H5 0.9300 . ?
C6 C7 1.495(4) . ?
C7 C8 1.348(4) . ?
C8 C9 1.492(3) . ?
C9 C10 1.384(4) . ?
C9 C11 1.388(4) . ?
C10 C11 1.375(4) 3_665 ?
C10 H10 0.9300 . ?
C11 C10 1.375(4) 3_665 ?
C11 H11 0.9300 . ?
C12 O1 1.440(4) . ?
C12 C13 1.455(6) . ?
C12 C15 1.516(5) . ?
C12 C14 1.562(6) . ?
C13 H13A 0.9600 . ?
C13 H13B 0.9600 . ?
C13 H13C 0.9600 . ?
C14 H14A 0.9600 . ?
C14 H14B 0.9600 . ?
C14 H14C 0.9600 . ?
C15 O2 1.452(4) . ?
C15 C17 1.477(5) . ?
C15 C16 1.530(6) . ?
C16 H16A 0.9600 . ?
C16 H16B 0.9600 . ?
C16 H16C 0.9600 . ?
C17 H17A 0.9600 . ?
C17 H17B 0.9600 . ?
C17 H17C 0.9600 . ?
C18 C21 1.458(6) . ?
C18 O3 1.462(4) . ?
C18 C19 1.487(5) . ?
C18 C20 1.587(6) . ?
C19 H19A 0.9600 . ?
C19 H19B 0.9600 . ?
C19 H19C 0.9600 . ?
C20 H20A 0.9600 . ?
C20 H20B 0.9600 . ?
C20 H20C 0.9600 . ?
C21 O4 1.471(4) . ?
C21 C23 1.487(6) . ?
C21 C22 1.626(7) . ?
C22 H22A 0.9600 . ?
C22 H22B 0.9600 . ?
C22 H22C 0.9600 . ?
C23 H23A 0.9600 . ?
C23 H23B 0.9600 . ?
C23 H23C 0.9600 . ?

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
O1 B1 O2 113.2(3) . . ?
O1 B1 C8 120.7(3) . . ?
O2 B1 C8 125.0(3) . . ?
O4 B2 O3 112.0(3) . . ?
O4 B2 C7 124.8(3) . . ?
O3 B2 C7 123.1(3) . . ?
C2 C1 C6 121.1(3) . . ?
C2 C1 H1 119.4 . . ?
C6 C1 H1 119.4 . . ?
C3 C2 C1 120.0(4) . . ?
C3 C2 H2 120.0 . . ?
C1 C2 H2 120.0 . . ?
C2 C3 C4 120.0(3) . . ?
C2 C3 H3 120.0 . . ?
C4 C3 H3 120.0 . . ?
C3 C4 C5 120.1(4) . . ?
C3 C4 H4 120.0 . . ?
C5 C4 H4 120.0 . . ?
C6 C5 C4 120.4(3) . . ?
C6 C5 H5 119.8 . . ?
C4 C5 H5 119.8 . . ?
C5 C6 C1 118.4(3) . . ?
C5 C6 C7 121.8(3) . . ?
C1 C6 C7 119.9(3) . . ?
C8 C7 C6 121.9(2) . . ?
C8 C7 B2 119.3(2) . . ?
C6 C7 B2 118.8(2) . . ?
C7 C8 C9 123.1(2) . . ?
C7 C8 B1 125.5(2) . . ?
C9 C8 B1 110.9(2) . . ?
C10 C9 C11 118.3(2) . . ?
C10 C9 C8 120.1(2) . . ?
C11 C9 C8 121.6(2) . . ?
C11 C10 C9 121.2(2) 3_665 . ?
C11 C10 H10 119.4 3_665 . ?
C9 C10 H10 119.4 . . ?
C10 C11 C9 120.5(3) 3_665 . ?
C10 C11 H11 119.7 3_665 . ?
C9 C11 H11 119.7 . . ?
O1 C12 C13 110.8(3) . . ?
O1 C12 C15 103.9(3) . . ?
C13 C12 C15 118.6(4) . . ?
O1 C12 C14 103.6(3) . . ?
C13 C12 C14 109.2(5) . . ?
C15 C12 C14 109.6(4) . . ?
C12 C13 H13A 109.5 . . ?
C12 C13 H13B 109.5 . . ?
H13A C13 H13B 109.5 . . ?
C12 C13 H13C 109.5 . . ?
H13A C13 H13C 109.5 . . ?
H13B C13 H13C 109.5 . . ?
C12 C14 H14A 109.5 . . ?
C12 C14 H14B 109.5 . . ?
H14A C14 H14B 109.5 . . ?
C12 C14 H14C 109.5 . . ?
H14A C14 H14C 109.5 . . ?
H14B C14 H14C 109.5 . . ?
O2 C15 C17 109.8(3) . . ?
O2 C15 C12 102.7(2) . . ?
C17 C15 C12 118.1(3) . . ?
O2 C15 C16 105.2(3) . . ?
C17 C15 C16 107.1(4) . . ?
C12 C15 C16 113.2(4) . . ?
C15 C16 H16A 109.5 . . ?
C15 C16 H16B 109.5 . . ?
H16A C16 H16B 109.5 . . ?
C15 C16 H16C 109.5 . . ?
H16A C16 H16C 109.5 . . ?
H16B C16 H16C 109.5 . . ?
C15 C17 H17A 109.5 . . ?
C15 C17 H17B 109.5 . . ?
H17A C17 H17B 109.5 . . ?
C15 C17 H17C 109.5 . . ?
H17A C17 H17C 109.5 . . ?
H17B C17 H17C 109.5 . . ?
C21 C18 O3 102.3(3) . . ?
C21 C18 C19 118.5(4) . . ?
O3 C18 C19 109.4(3) . . ?
C21 C18 C20 107.2(4) . . ?
O3 C18 C20 107.5(3) . . ?
C19 C18 C20 111.2(3) . . ?
C18 C19 H19A 109.5 . . ?
C18 C19 H19B 109.5 . . ?
H19A C19 H19B 109.5 . . ?
C18 C19 H19C 109.5 . . ?
H19A C19 H19C 109.5 . . ?
H19B C19 H19C 109.5 . . ?
C18 C20 H20A 109.5 . . ?
C18 C20 H20B 109.5 . . ?
H20A C20 H20B 109.5 . . ?
C18 C20 H20C 109.5 . . ?
H20A C20 H20C 109.5 . . ?
H20B C20 H20C 109.5 . . ?
C18 C21 O4 103.3(3) . . ?
C18 C21 C23 121.8(4) . . ?
O4 C21 C23 107.1(4) . . ?
C18 C21 C22 107.1(4) . . ?
O4 C21 C22 106.5(4) . . ?
C23 C21 C22 109.9(5) . . ?
C21 C22 H22A 109.5 . . ?
C21 C22 H22B 109.5 . . ?
H22A C22 H22B 109.5 . . ?
C21 C22 H22C 109.5 . . ?
H22A C22 H22C 109.5 . . ?
H22B C22 H22C 109.5 . . ?
C21 C23 H23A 109.5 . . ?
C21 C23 H23B 109.5 . . ?
H23A C23 H23B 109.5 . . ?
C21 C23 H23C 109.5 . . ?
H23A C23 H23C 109.5 . . ?
H23B C23 H23C 109.5 . . ?
B1 O1 C12 107.1(2) . . ?
B1 O2 C15 107.4(3) . . ?
B2 O3 C18 108.0(2) . . ?
B2 O4 C21 106.8(3) . . ?

_diffrn_measured_fraction_theta_max 0.996
_diffrn_reflns_theta_full        25.00
_diffrn_measured_fraction_theta_full 0.996
_refine_diff_density_max         0.607
_refine_diff_density_min         -0.379
_refine_diff_density_rms         0.047
####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_a
_database_code_depnum_ccdc_archive 'CCDC 1415296'
_audit_update_record             
;
2015-07-26 deposited with the CCDC.
2015-09-08 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C14 H9 I'
_chemical_formula_weight         304.11

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'
I I -0.4742 1.8119 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           Orthorhombic
_symmetry_space_group_name_H-M   Pnma

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

_cell_length_a                   23.161(13)
_cell_length_b                   9.844(6)
_cell_length_c                   4.833(3)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_volume                     1101.9(11)
_cell_formula_units_Z            4
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    3901
_cell_measurement_theta_min      2.72
_cell_measurement_theta_max      28.55

_exptl_crystal_description       block
_exptl_crystal_colour            light-green
_exptl_crystal_size_max          0.32
_exptl_crystal_size_mid          0.28
_exptl_crystal_size_min          0.21
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.833
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             584
_exptl_absorpt_coefficient_mu    2.867
_exptl_absorpt_correction_type   Multi-scan
_exptl_absorpt_correction_T_min  0.4607
_exptl_absorpt_correction_T_max  0.5843
_exptl_absorpt_process_details   SADABS

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            4913
_diffrn_reflns_av_R_equivalents  0.0439
_diffrn_reflns_av_sigmaI/netI    0.0349
_diffrn_reflns_limit_h_min       -27
_diffrn_reflns_limit_h_max       23
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_l_min       -4
_diffrn_reflns_limit_l_max       5
_diffrn_reflns_theta_min         2.72
_diffrn_reflns_theta_max         24.99
_reflns_number_total             1026
_reflns_number_gt                974
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'

_refine_special_details          
; 
 Refinement of F² against ALL reflections.  The weighted R-factor wR and 
 goodness of fit S are based on F², conventional R-factors R are based 
 on F, with F set to zero for negative F². The threshold expression of 
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is 
 not relevant to the choice of reflections for refinement.  R-factors based 
 on F² are statistically about twice as large as those based on F, and R- 
 factors based on ALL data will be even larger. 
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0439P)²+1.3962P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     SHELXL
_refine_ls_extinction_coef       0.0233(17)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         1026
_refine_ls_number_parameters     80
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0349
_refine_ls_R_factor_gt           0.0334
_refine_ls_wR_factor_ref         0.0789
_refine_ls_wR_factor_gt          0.0778
_refine_ls_goodness_of_fit_ref   1.019
_refine_ls_restrained_S_all      1.019
_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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
I1 I -0.028665(13) 0.7500 -0.37660(6) 0.0530(2) Uani 1 2 d S . .
C1 C 0.34291(18) 0.7500 1.2398(9) 0.0399(10) Uani 1 2 d S . .
H1 H 0.3708 0.7500 1.3783 0.048 Uiso 1 2 calc SR . .
C2 C 0.32207(15) 0.6293(4) 1.1363(6) 0.0405(8) Uani 1 1 d . . .
H2 H 0.3361 0.5474 1.2049 0.049 Uiso 1 1 calc R . .
C3 C 0.28120(14) 0.6286(3) 0.9352(6) 0.0362(7) Uani 1 1 d . . .
H3 H 0.2676 0.5463 0.8663 0.043 Uiso 1 1 calc R . .
C4 C 0.25942(18) 0.7500 0.8313(8) 0.0291(8) Uani 1 2 d S . .
C5 C 0.21593(19) 0.7500 0.6260(8) 0.0333(9) Uani 1 2 d S . .
C6 C 0.17839(19) 0.7500 0.4562(9) 0.0341(9) Uani 1 2 d S . .
C7 C 0.13290(17) 0.7500 0.2567(9) 0.0346(9) Uani 1 2 d S . .
C8 C 0.11041(15) 0.6289(4) 0.1580(6) 0.0418(8) Uani 1 1 d . . .
H8 H 0.1257 0.5468 0.2190 0.050 Uiso 1 1 calc R . .
C9 C 0.06560(14) 0.6291(4) -0.0297(7) 0.0423(8) Uani 1 1 d . . .
H9 H 0.0504 0.5477 -0.0948 0.051 Uiso 1 1 calc R . .
C10 C 0.0438(2) 0.7500 -0.1187(8) 0.0395(10) Uani 1 2 d S . .


_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
I1 C10 2.091(5) . ?
C1 C2 1.377(4) . ?
C1 C2 1.377(4) 8_575 ?
C1 H1 0.9300 . ?
C2 C3 1.357(4) . ?
C2 H2 0.9300 . ?
C3 C4 1.391(4) . ?
C3 H3 0.9300 . ?
C4 C3 1.391(4) 8_575 ?
C4 C5 1.414(6) . ?
C5 C6 1.196(6) . ?
C6 C7 1.428(6) . ?
C7 C8 1.386(4) . ?
C7 C8 1.386(4) 8_575 ?
C8 C9 1.379(5) . ?
C8 H8 0.9300 . ?
C9 C10 1.363(4) . ?
C9 H9 0.9300 . ?
C10 C9 1.363(4) 8_575 ?

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 C2 119.4(4) . 8_575 ?
C2 C1 H1 120.3 . . ?
C2 C1 H1 120.3 8_575 . ?
C3 C2 C1 120.6(3) . . ?
C3 C2 H2 119.7 . . ?
C1 C2 H2 119.7 . . ?
C2 C3 C4 120.5(3) . . ?
C2 C3 H3 119.8 . . ?
C4 C3 H3 119.8 . . ?
C3 C4 C3 118.5(4) 8_575 . ?
C3 C4 C5 120.77(19) 8_575 . ?
C3 C4 C5 120.77(19) . . ?
C6 C5 C4 178.8(4) . . ?
C5 C6 C7 179.1(5) . . ?
C8 C7 C8 118.7(4) . 8_575 ?
C8 C7 C6 120.6(2) . . ?
C8 C7 C6 120.6(2) 8_575 . ?
C9 C8 C7 120.6(3) . . ?
C9 C8 H8 119.7 . . ?
C7 C8 H8 119.7 . . ?
C10 C9 C8 119.2(3) . . ?
C10 C9 H9 120.4 . . ?
C8 C9 H9 120.4 . . ?
C9 C10 C9 121.8(4) 8_575 . ?
C9 C10 I1 119.1(2) 8_575 . ?
C9 C10 I1 119.1(2) . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C2 C1 C2 C3 -0.3(6) 8_575 . . . ?
C1 C2 C3 C4 -0.4(5) . . . . ?
C2 C3 C4 C3 1.0(6) . . . 8_575 ?
C2 C3 C4 C5 -178.6(3) . . . . ?
C3 C4 C5 C6 -89.8(3) 8_575 . . . ?
C3 C4 C5 C6 89.8(3) . . . . ?
C4 C5 C6 C7 0.00(9) . . . . ?
C5 C6 C7 C8 -90.0(4) . . . . ?
C5 C6 C7 C8 90.0(4) . . . 8_575 ?
C8 C7 C8 C9 -1.5(7) 8_575 . . . ?
C6 C7 C8 C9 178.5(4) . . . . ?
C7 C8 C9 C10 0.4(6) . . . . ?
C8 C9 C10 C9 0.8(7) . . . 8_575 ?
C8 C9 C10 I1 -174.8(3) . . . . ?

_diffrn_measured_fraction_theta_max 0.998
_diffrn_reflns_theta_full        24.99
_diffrn_measured_fraction_theta_full 0.998
_refine_diff_density_max         0.854
_refine_diff_density_min         -1.165
_refine_diff_density_rms         0.145
####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_a
_database_code_depnum_ccdc_archive 'CCDC 1415297'
_audit_update_record             
;
2015-07-26 deposited with the CCDC.
2015-09-08 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C22 H16 S2'
_chemical_formula_weight         344.47

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'

_symmetry_cell_setting           Monoclinic
_symmetry_space_group_name_H-M   'P2(1)   '

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

_cell_length_a                   9.831(5)
_cell_length_b                   9.580(4)
_cell_length_c                   10.090(3)
_cell_angle_alpha                90.00
_cell_angle_beta                 105.875(19)
_cell_angle_gamma                90.00
_cell_volume                     914.1(6)
_cell_formula_units_Z            2
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    1010
_cell_measurement_theta_min      2.56
_cell_measurement_theta_max      19.17

_exptl_crystal_description       block
_exptl_crystal_colour            yellow
_exptl_crystal_size_max          0.26
_exptl_crystal_size_mid          0.21
_exptl_crystal_size_min          0.17
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.251
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             360
_exptl_absorpt_coefficient_mu    0.290
_exptl_absorpt_correction_type   Multi-scan
_exptl_absorpt_correction_T_min  0.9283
_exptl_absorpt_correction_T_max  0.9523
_exptl_absorpt_process_details   SADABS

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      296(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            4612
_diffrn_reflns_av_R_equivalents  0.0313
_diffrn_reflns_av_sigmaI/netI    0.0768
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_l_min       -7
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_theta_min         2.56
_diffrn_reflns_theta_max         25.00
_reflns_number_total             3082
_reflns_number_gt                1902
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'

_refine_special_details          
; 
 Refinement of F² against ALL reflections.  The weighted R-factor wR and 
 goodness of fit S are based on F², conventional R-factors R are based 
 on F, with F set to zero for negative F². The threshold expression of 
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is 
 not relevant to the choice of reflections for refinement.  R-factors based 
 on F² are statistically about twice as large as those based on F, and R- 
 factors based on ALL data will be even larger. 
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0200P)²+1.9000P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     SHELXL
_refine_ls_extinction_coef       0.066(8)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         3082
_refine_ls_number_parameters     218
_refine_ls_number_restraints     7
_refine_ls_R_factor_all          0.1483
_refine_ls_R_factor_gt           0.1002
_refine_ls_wR_factor_ref         0.2281
_refine_ls_wR_factor_gt          0.2058
_refine_ls_goodness_of_fit_ref   1.070
_refine_ls_restrained_S_all      1.091
_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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
S1 S 0.6607(4) 0.2524(5) -0.0645(3) 0.1483(16) Uani 1 1 d . . .
S2 S 0.8351(4) 0.5491(5) 0.0676(4) 0.1492(15) Uani 1 1 d . . .
C14 C 1.0070(5) 0.3538(7) 0.2021(5) 0.0372(12) Uani 1 1 d . . .
H14 H 1.0467 0.2814 0.2616 0.045 Uiso 1 1 calc R . .
C17 C 0.8203(7) 0.3587(8) 0.4106(7) 0.0596(18) Uani 1 1 d D . .
C11 C 0.4881(8) 0.4002(8) 0.3673(8) 0.069(2) Uani 1 1 d . . .
H11 H 0.5339 0.4860 0.3810 0.083 Uiso 1 1 calc R . .
C12 C 0.7601(7) 0.3676(8) 0.2587(7) 0.0627(19) Uani 1 1 d . . .
C5 C 0.6232(8) 0.3341(9) 0.1919(8) 0.070(2) Uani 1 1 d . . .
C10 C 0.3944(9) 0.3682(11) 0.4363(8) 0.079(2) Uani 1 1 d . . .
H10 H 0.3766 0.4327 0.4985 0.095 Uiso 1 1 calc R . .
C2 C 0.4093(7) 0.3623(8) -0.0395(6) 0.0565(18) Uani 1 1 d . . .
H2 H 0.3395 0.4037 -0.0064 0.068 Uiso 1 1 calc R . .
C6 C 0.5179(8) 0.3021(8) 0.2723(7) 0.0629(19) Uani 1 1 d . . .
C21 C 0.9719(10) 0.4501(11) 0.6199(9) 0.089(3) Uani 1 1 d D . .
H21 H 1.0312 0.5201 0.6671 0.107 Uiso 1 1 calc R . .
C22 C 0.9135(8) 0.4623(9) 0.4815(7) 0.069(2) Uani 1 1 d D . .
H22 H 0.9352 0.5387 0.4342 0.083 Uiso 1 1 calc R . .
C3 C 0.4072(11) 0.3131(12) -0.1883(9) 0.097(3) Uani 1 1 d . . .
H3 H 0.3260 0.3178 -0.2617 0.117 Uiso 1 1 calc R . .
C1 C 0.5702(8) 0.3188(8) 0.0386(7) 0.064(2) Uani 1 1 d . . .
C9 C 0.3230(8) 0.2428(13) 0.4186(9) 0.084(3) Uani 1 1 d . . .
H9 H 0.2576 0.2236 0.4675 0.101 Uiso 1 1 calc R . .
C13 C 0.8595(7) 0.4177(8) 0.1736(7) 0.0584(18) Uani 1 1 d . . .
C7 C 0.4443(9) 0.1744(9) 0.2536(8) 0.074(2) Uani 1 1 d . . .
H7 H 0.4600 0.1092 0.1911 0.089 Uiso 1 1 calc R . .
C18 C 0.7978(9) 0.2404(11) 0.4924(10) 0.085(3) Uani 1 1 d D . .
H18 H 0.7426 0.1653 0.4504 0.101 Uiso 1 1 calc R . .
C8 C 0.3495(10) 0.1460(10) 0.3277(9) 0.082(3) Uani 1 1 d . . .
H8 H 0.3026 0.0606 0.3165 0.099 Uiso 1 1 calc R . .
C15 C 1.0698(11) 0.4361(14) 0.1113(12) 0.109(4) Uani 1 1 d . . .
H15 H 1.1608 0.4180 0.1053 0.131 Uiso 1 1 calc R . .
C19 C 0.8501(12) 0.2406(12) 0.6123(13) 0.105(3) Uani 1 1 d D . .
H19 H 0.8252 0.1670 0.6611 0.126 Uiso 1 1 calc R . .
C4 C 0.5240(13) 0.2661(11) -0.2024(9) 0.096(3) Uani 1 1 d . . .
H4 H 0.5321 0.2401 -0.2887 0.115 Uiso 1 1 calc R . .
C20 C 0.9447(12) 0.3374(12) 0.6900(10) 0.106(4) Uani 1 1 d D . .
H20 H 0.9866 0.3255 0.7838 0.128 Uiso 1 1 calc R . .
C16 C 0.9897(14) 0.5408(14) 0.0357(11) 0.108(4) Uani 1 1 d . . .
H16 H 1.0189 0.5988 -0.0251 0.130 Uiso 1 1 calc R . .


_geom_special_details            
; 
 All esds (except the esd in the dihedral angle between two l.s. planes) 
 are estimated using the full covariance matrix.  The cell esds are taken 
 into account individually in the estimation of esds in distances, angles 
 and torsion angles; correlations between esds in cell parameters are only 
 used when they are defined by crystal symmetry.  An approximate (isotropic) 
 treatment of cell esds is used for estimating esds involving l.s. planes. 
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
S1 C4 1.654(10) . ?
S1 C1 1.669(8) . ?
S2 C13 1.626(8) . ?
S2 C16 1.640(12) . ?
C14 C15 1.467(14) . ?
C14 C13 1.527(8) . ?
C14 H14 0.9300 . ?
C17 C22 1.407(9) . ?
C17 C18 1.454(10) . ?
C17 C12 1.487(9) . ?
C11 C10 1.334(11) . ?
C11 C6 1.429(11) . ?
C11 H11 0.9300 . ?
C12 C5 1.368(10) . ?
C12 C13 1.543(9) . ?
C5 C1 1.498(10) . ?
C5 C6 1.512(11) . ?
C10 C9 1.378(13) . ?
C10 H10 0.9300 . ?
C2 C3 1.569(11) . ?
C2 C1 1.617(9) . ?
C2 H2 0.9300 . ?
C6 C7 1.407(11) . ?
C21 C20 1.356(12) . ?
C21 C22 1.362(10) . ?
C21 H21 0.9300 . ?
C22 H22 0.9300 . ?
C3 C4 1.277(14) . ?
C3 H3 0.9300 . ?
C9 C8 1.378(13) . ?
C9 H9 0.9300 . ?
C7 C8 1.373(12) . ?
C7 H7 0.9300 . ?
C18 C19 1.178(11) . ?
C18 H18 0.9300 . ?
C8 H8 0.9300 . ?
C15 C16 1.370(16) . ?
C15 H15 0.9300 . ?
C19 C20 1.394(12) . ?
C19 H19 0.9300 . ?
C4 H4 0.9300 . ?
C20 H20 0.9300 . ?
C16 H16 0.9300 . ?

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
C4 S1 C1 92.6(5) . . ?
C13 S2 C16 96.5(6) . . ?
C15 C14 C13 101.9(7) . . ?
C15 C14 H14 129.0 . . ?
C13 C14 H14 129.0 . . ?
C22 C17 C18 116.2(7) . . ?
C22 C17 C12 120.3(7) . . ?
C18 C17 C12 123.4(7) . . ?
C10 C11 C6 119.8(8) . . ?
C10 C11 H11 120.1 . . ?
C6 C11 H11 120.1 . . ?
C5 C12 C17 123.7(7) . . ?
C5 C12 C13 119.1(6) . . ?
C17 C12 C13 117.2(6) . . ?
C12 C5 C1 123.3(7) . . ?
C12 C5 C6 120.6(7) . . ?
C1 C5 C6 116.0(6) . . ?
C11 C10 C9 122.1(9) . . ?
C11 C10 H10 118.9 . . ?
C9 C10 H10 118.9 . . ?
C3 C2 C1 98.3(6) . . ?
C3 C2 H2 130.9 . . ?
C1 C2 H2 130.9 . . ?
C7 C6 C11 118.0(7) . . ?
C7 C6 C5 120.4(7) . . ?
C11 C6 C5 121.5(7) . . ?
C20 C21 C22 121.0(9) . . ?
C20 C21 H21 119.5 . . ?
C22 C21 H21 119.5 . . ?
C21 C22 C17 119.6(8) . . ?
C21 C22 H22 120.2 . . ?
C17 C22 H22 120.2 . . ?
C4 C3 C2 115.8(8) . . ?
C4 C3 H3 122.1 . . ?
C2 C3 H3 122.1 . . ?
C5 C1 C2 119.7(6) . . ?
C5 C1 S1 125.9(6) . . ?
C2 C1 S1 114.3(5) . . ?
C10 C9 C8 119.4(8) . . ?
C10 C9 H9 120.3 . . ?
C8 C9 H9 120.3 . . ?
C14 C13 C12 118.9(6) . . ?
C14 C13 S2 113.3(5) . . ?
C12 C13 S2 127.2(5) . . ?
C8 C7 C6 120.0(8) . . ?
C8 C7 H7 120.0 . . ?
C6 C7 H7 120.0 . . ?
C19 C18 C17 119.3(11) . . ?
C19 C18 H18 120.3 . . ?
C17 C18 H18 120.3 . . ?
C7 C8 C9 120.6(9) . . ?
C7 C8 H8 119.7 . . ?
C9 C8 H8 119.7 . . ?
C16 C15 C14 117.7(9) . . ?
C16 C15 H15 121.1 . . ?
C14 C15 H15 121.1 . . ?
C18 C19 C20 128.0(12) . . ?
C18 C19 H19 116.0 . . ?
C20 C19 H19 116.0 . . ?
C3 C4 S1 118.9(8) . . ?
C3 C4 H4 120.6 . . ?
S1 C4 H4 120.6 . . ?
C21 C20 C19 115.7(9) . . ?
C21 C20 H20 122.2 . . ?
C19 C20 H20 122.2 . . ?
C15 C16 S2 110.4(8) . . ?
C15 C16 H16 124.8 . . ?
S2 C16 H16 124.8 . . ?

_diffrn_measured_fraction_theta_max 0.990
_diffrn_reflns_theta_full        25.00
_diffrn_measured_fraction_theta_full 0.990
_refine_diff_density_max         0.336
_refine_diff_density_min         -0.373
_refine_diff_density_rms         0.073
