# Electronic Supplementary Material (ESI) for Chemical Science.
# This journal is © The Royal Society of Chemistry 2017

####################################################################### 
# 
# 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_yoshi43s
_database_code_depnum_ccdc_archive 'CCDC 1523264'
_audit_update_record             
;
2016-12-18 deposited with the CCDC.
2017-04-07 downloaded from the CCDC.
;
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C14 H8 S Te'
_chemical_formula_iupac          ?
_chemical_formula_weight         335.86

_chemical_melting_point          ?

_space_group_crystal_system      monoclinic
_space_group_name_H-M_alt        'P 1 21/c 1'
_space_group_name_Hall           '-P 2ybc'
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                   8.8331(14)
_cell_length_b                   8.9989(16)
_cell_length_c                   14.460(2)
_cell_angle_alpha                90
_cell_angle_beta                 95.546(5)
_cell_angle_gamma                90
_cell_volume                     1144.0(3)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    4518
_cell_measurement_theta_min      2.2631
_cell_measurement_theta_max      25.4883
_cell_measurement_temperature    103.(2)

_exptl_crystal_description       plate
_exptl_crystal_colour            yellow
_exptl_crystal_size_max          0.380
_exptl_crystal_size_mid          0.340
_exptl_crystal_size_min          0.040
_exptl_crystal_density_diffrn    1.950
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             640

_exptl_absorpt_coefficient_mu    2.747
_exptl_absorpt_correction_type   Multi-Scan
_exptl_absorpt_process_details   
;
SADABS-2014/5 - Bruker AXS area detector scaling and absorption correction
;
_exptl_absorpt_correction_T_min  0.61
_exptl_absorpt_correction_T_max  0.90

_exptl_special_details           
;
;

_diffrn_ambient_temperature      103.(2)

_diffrn_source                   'fine-focus sealed tube'
_diffrn_source_type              'Bruker KappaCCD'

_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_monochromator  graphite

_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'

_diffrn_detector_area_resol_mean 8.3333

_diffrn_reflns_number            11206
_diffrn_reflns_av_R_equivalents  0.0643
_diffrn_reflns_av_unetI/netI     0.0497
_diffrn_reflns_theta_min         2.32
_diffrn_reflns_theta_max         25.49
_diffrn_reflns_theta_full        25.49
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measured_fraction_theta_full 0.997
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_limit_l_max       17

_refine_special_details          
;


Refined as a 2-component twin.
;

_reflns_number_total             2117
_reflns_number_gt                1827
_reflns_threshold_expression     'I > 2σ(I)'

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_R_factor_all          0.0965
_refine_ls_R_factor_gt           0.0852
_refine_ls_wR_factor_gt          0.1814
_refine_ls_wR_factor_ref         0.1864
_refine_ls_goodness_of_fit_ref   1.303
_refine_ls_restrained_S_all      1.264
_refine_ls_number_reflns         2117
_refine_ls_number_parameters     164
_refine_ls_number_restraints     177
_refine_ls_number_constraints    ?
_refine_ls_hydrogen_treatment    constr
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+27.7820P] where P=(Fo²+2Fc²)/3'

_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?

_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_diff_density_max         1.941
_refine_diff_density_min         -1.862
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?

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'
Te Te -0.5308 1.6751 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_computing_data_collection       'APEX3 (Bruker AXS Inc., 2015)'
_computing_cell_refinement       'SAINT V8.35A (Bruker AXS Inc., 2015)'
_computing_data_reduction        'SAINT V8.35A (Bruker AXS Inc., 2015)'
_computing_structure_solution    'XT, VERSION 2014/4'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    'XP (Bruker AXS Inc., 2015)'
_computing_publication_material  'APEX3 (Bruker AXS Inc., 2015)'

loop_
_atom_site_type_symbol
_atom_site_label
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_calc_flag
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_refinement_flags_posn
_atom_site_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
S S1 0.6314(8) 0.5126(9) 0.6694(5) 0.0183(15) Uani d U P . 0.619(4) A 1
Te Te1 0.2186(2) 0.7827(2) 0.57096(13) 0.0210(5) Uani d U P . 0.619(4) A 1
S S1A 0.2555(12) 0.7462(12) 0.5952(8) 0.020(2) Uani d U P . 0.381(4) A 2
Te Te1A 0.6726(4) 0.4702(4) 0.6806(2) 0.0177(8) Uani d U P . 0.381(4) A 2
C C1 0.6818(11) 0.6063(11) 0.5693(7) 0.0177(19) Uani d U . . 1.0 . .
C C2 0.8171(13) 0.6045(13) 0.5253(9) 0.030(2) Uani d U . . 1.0 . .
H H2 0.9017 0.547 0.55 0.036 Uiso calc U . R 1.0 . .
C C3 0.8251(16) 0.6857(15) 0.4475(9) 0.039(3) Uani d U . . 1.0 . .
H H3 0.9144 0.6806 0.4159 0.047 Uiso calc U . R 1.0 . .
C C4 0.7092(16) 0.7741(15) 0.4135(9) 0.039(3) Uani d U . . 1.0 . .
H H4 0.7198 0.8344 0.3606 0.047 Uiso calc U . R 1.0 . .
C C5 0.5724(15) 0.7771(14) 0.4562(8) 0.035(2) Uani d U . . 1.0 . .
H H5 0.4903 0.8376 0.4312 0.042 Uiso calc U . R 1.0 . .
C C6 0.5577(12) 0.6922(11) 0.5345(7) 0.0205(19) Uani d U . . 1.0 . .
C C7 0.4322(12) 0.6801(13) 0.5885(8) 0.026(2) Uani d U . . 1.0 . .
C C8 0.4538(12) 0.5835(12) 0.6634(8) 0.024(2) Uani d U . . 1.0 . .
C C9 0.3303(12) 0.5642(12) 0.7207(8) 0.022(2) Uani d U . . 1.0 . .
C C10 0.2026(12) 0.6519(11) 0.6912(7) 0.0198(19) Uani d U . . 1.0 . .
C C11 0.0732(13) 0.6472(11) 0.7390(8) 0.023(2) Uani d U . . 1.0 . .
H H11 -0.0133 0.7054 0.7185 0.028 Uiso calc U . R 1.0 . .
C C12 0.0714(12) 0.5572(11) 0.8164(7) 0.021(2) Uani d U . . 1.0 . .
H H12 -0.0163 0.5543 0.8495 0.025 Uiso calc U . R 1.0 . .
C C13 0.1988(13) 0.4702(12) 0.8461(8) 0.023(2) Uani d U . . 1.0 . .
H H13 0.1969 0.4083 0.8992 0.028 Uiso calc U . R 1.0 . .
C C14 0.3243(12) 0.4742(12) 0.7995(7) 0.022(2) Uani d U . . 1.0 . .
H H14 0.4099 0.415 0.8204 0.026 Uiso calc U . R 1.0 . .


_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_site_symmetry_2
_geom_bond_distance
_geom_bond_publ_flag
S1 C8 . 1.688(13) ?
S1 C1 . 1.769(13) ?
Te1 C7 . 2.093(11) ?
Te1 C10 . 2.116(11) ?
S1A C7 . 1.682(15) ?
S1A C10 . 1.730(15) ?
Te1A C1 . 2.030(11) ?
Te1A C8 . 2.177(11) ?
C1 C6 . 1.395(14) ?
C1 C2 . 1.407(15) ?
C2 C3 . 1.349(18) ?
C3 C4 . 1.35(2) ?
C4 C5 . 1.409(19) ?
C5 C6 . 1.383(16) ?
C6 C7 . 1.420(16) ?
C7 C8 . 1.388(16) ?
C8 C9 . 1.444(16) ?
C9 C14 . 1.402(16) ?
C9 C10 . 1.409(15) ?
C10 C11 . 1.391(15) ?
C11 C12 . 1.383(15) ?
C12 C13 . 1.404(15) ?
C13 C14 . 1.352(16) ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle
_geom_angle_publ_flag
C8 S1 C1 . . 94.8(6) ?
C7 Te1 C10 . . 77.7(4) ?
C7 S1A C10 . . 101.4(8) ?
C1 Te1A C8 . . 74.4(4) ?
C6 C1 C2 . . 121.0(10) ?
C6 C1 S1 . . 107.9(8) ?
C2 C1 S1 . . 131.1(9) ?
C6 C1 Te1A . . 122.0(8) ?
C2 C1 Te1A . . 116.9(8) ?
C3 C2 C1 . . 119.1(12) ?
C2 C3 C4 . . 121.6(13) ?
C3 C4 C5 . . 120.2(13) ?
C6 C5 C4 . . 120.1(12) ?
C5 C6 C1 . . 117.9(11) ?
C5 C6 C7 . . 129.2(11) ?
C1 C6 C7 . . 112.8(10) ?
C8 C7 C6 . . 114.9(10) ?
C8 C7 S1A . . 103.6(9) ?
C6 C7 S1A . . 141.5(10) ?
C8 C7 Te1 . . 115.2(8) ?
C6 C7 Te1 . . 129.9(9) ?
C7 C8 C9 . . 118.0(10) ?
C7 C8 S1 . . 109.5(9) ?
C9 C8 S1 . . 132.5(9) ?
C7 C8 Te1A . . 115.9(8) ?
C9 C8 Te1A . . 126.2(8) ?
C14 C9 C10 . . 118.5(10) ?
C14 C9 C8 . . 128.7(10) ?
C10 C9 C8 . . 112.7(10) ?
C11 C10 C9 . . 120.3(10) ?
C11 C10 S1A . . 135.4(9) ?
C9 C10 S1A . . 104.3(9) ?
C11 C10 Te1 . . 123.2(8) ?
C9 C10 Te1 . . 116.4(8) ?
C12 C11 C10 . . 119.6(10) ?
C11 C12 C13 . . 120.2(11) ?
C14 C13 C12 . . 120.3(10) ?
C13 C14 C9 . . 121.1(10) ?

####################################################################### 
# 
# 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_yoshi42s
_database_code_depnum_ccdc_archive 'CCDC 1523263'
_audit_update_record             
;
2016-12-18 deposited with the CCDC.
2017-04-07 downloaded from the CCDC.
;
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C14 H8 S Te'
_chemical_formula_iupac          ?
_chemical_formula_weight         335.86
_chemical_absolute_configuration ?

_chemical_melting_point          ?

_space_group_crystal_system      monoclinic
_space_group_name_H-M_alt        'P 1 21 1'
_space_group_name_Hall           'P 2yb'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z'

_cell_length_a                   9.6238(13)
_cell_length_b                   4.2326(6)
_cell_length_c                   13.660(2)
_cell_angle_alpha                90
_cell_angle_beta                 98.795(5)
_cell_angle_gamma                90
_cell_volume                     549.88(14)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    2821
_cell_measurement_theta_min      2.4237
_cell_measurement_theta_max      29.6202
_cell_measurement_temperature    103.(2)

_exptl_crystal_description       needle
_exptl_crystal_colour            yellow
_exptl_crystal_size_max          0.240
_exptl_crystal_size_mid          0.060
_exptl_crystal_size_min          0.040
_exptl_crystal_density_diffrn    2.028
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             320

_exptl_absorpt_coefficient_mu    2.858
_exptl_absorpt_correction_type   Multi-Scan
_exptl_absorpt_process_details   
;
SADABS-2014/5 - Bruker AXS area detector scaling and absorption correction
;
_exptl_absorpt_correction_T_min  0.64
_exptl_absorpt_correction_T_max  0.89

_exptl_special_details           
;
;

_diffrn_ambient_temperature      103.(2)

_diffrn_source                   'fine-focus sealed tube'
_diffrn_source_type              'Bruker KappaCCD'

_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_monochromator  graphite

_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'

_diffrn_detector_area_resol_mean 8.3333

_diffrn_reflns_number            8540
_diffrn_reflns_av_R_equivalents  0.0404
_diffrn_reflns_av_unetI/netI     0.0588
_diffrn_reflns_theta_min         1.51
_diffrn_reflns_theta_max         31.02
_diffrn_reflns_theta_full        31.02
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_k_min       -6
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_limit_l_max       19

_refine_special_details          
;
;

_reflns_number_total             3486
_reflns_number_gt                3132
_reflns_threshold_expression     'I > 2σ(I)'

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_R_factor_all          0.0385
_refine_ls_R_factor_gt           0.0325
_refine_ls_wR_factor_gt          0.0669
_refine_ls_wR_factor_ref         0.0692
_refine_ls_goodness_of_fit_ref   1.058
_refine_ls_restrained_S_all      1.056
_refine_ls_number_reflns         3486
_refine_ls_number_parameters     164
_refine_ls_number_restraints     40
_refine_ls_number_constraints    ?
_refine_ls_hydrogen_treatment    constr
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0254P)²] where P=(Fo²+2Fc²)/3'

_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?

_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_diff_density_max         0.514
_refine_diff_density_min         -0.888
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_abs_structure_details 
;

Flack x determined using 1210 quotients [(I+)-(I-)]/[(I+)+(I-)]
(Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.03(2)

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'
Te Te -0.5308 1.6751 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_computing_data_collection       'APEX3 (Bruker AXS Inc., 2015)'
_computing_cell_refinement       'SAINT V8.35A (Bruker AXS Inc., 2015)'
_computing_data_reduction        'SAINT V8.35A (Bruker AXS Inc., 2015)'
_computing_structure_solution    'XS, VERSION 2013/1'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    'XP (Bruker AXS Inc., 2015)'
_computing_publication_material  'APEX3 (Bruker AXS Inc., 2015)'

loop_
_atom_site_type_symbol
_atom_site_label
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_calc_flag
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_refinement_flags_posn
_atom_site_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Te Te1 0.36577(5) 1.25965(13) 0.04631(3) 0.01222(10) Uani d U P D 0.9139(13) A
1
S S1 0.6918(4) 1.2466(13) 0.1901(3) 0.0152(6) Uani d U P D 0.9139(13) A 1
Te Te1A 0.7158(11) 1.277(4) 0.1765(8) 0.0180(18) Uani d U P D 0.0861(13) A 2
S S1A 0.372(2) 1.219(6) 0.0714(14) 0.013(2) Uani d U P D 0.0861(13) A 2
C C1 0.2417(5) 1.0154(12) 0.1335(4) 0.0128(10) Uani d . . D 1.0 . .
C C2 0.0984(6) 0.9579(13) 0.1078(4) 0.0175(11) Uani d . . . 1.0 . .
H H2 0.0491 1.0363 0.0471 0.021 Uiso calc U . R 1.0 . .
C C3 0.0287(5) 0.788(3) 0.1704(4) 0.0205(14) Uani d . . . 1.0 . .
H H3 -0.0694 0.7511 0.1534 0.025 Uiso calc U . R 1.0 . .
C C4 0.1013(6) 0.6688(13) 0.2590(5) 0.0212(13) Uani d . . . 1.0 . .
H H4 0.0531 0.5455 0.3012 0.025 Uiso calc U . R 1.0 . .
C C5 0.2439(5) 0.730(3) 0.2856(4) 0.0158(15) Uani d . . . 1.0 . .
H H5 0.2918 0.6521 0.3468 0.019 Uiso calc U . R 1.0 . .
C C6 0.3182(5) 0.9041(12) 0.2237(4) 0.0121(10) Uani d . . . 1.0 . .
C C7 0.4666(6) 0.9869(13) 0.2413(4) 0.0127(10) Uani d . . . 1.0 . .
C C8 0.5142(5) 1.1554(12) 0.1664(4) 0.0131(10) Uani d . . D 1.0 . .
C C9 0.5795(5) 0.9222(12) 0.3220(4) 0.0106(10) Uani d . . . 1.0 . .
C C10 0.7078(6) 1.0479(12) 0.3046(4) 0.0139(10) Uani d . . D 1.0 . .
C C11 0.8321(6) 1.0137(13) 0.3718(4) 0.0175(11) Uani d . . . 1.0 . .
H H11 0.9184 1.0981 0.3577 0.021 Uiso calc U . R 1.0 . .
C C12 0.8259(6) 0.8553(12) 0.4583(4) 0.0188(12) Uani d . . . 1.0 . .
H H12 0.9087 0.8325 0.5055 0.023 Uiso calc U . R 1.0 . .
C C13 0.7006(6) 0.728(3) 0.4779(4) 0.0204(16) Uani d . . . 1.0 . .
H H13 0.6988 0.6146 0.5377 0.025 Uiso calc U . R 1.0 . .
C C14 0.5779(5) 0.763(4) 0.4115(3) 0.0163(9) Uani d . . . 1.0 . .
H H14 0.4923 0.6793 0.4268 0.02 Uiso calc U . R 1.0 . .


_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_site_symmetry_2
_geom_bond_distance
_geom_bond_publ_flag
Te1 C8 . 2.051(5) ?
Te1 C1 . 2.085(5) ?
S1 C8 . 1.735(6) ?
S1 C10 . 1.761(7) ?
Te1A C8 . 1.992(12) ?
Te1A C10 . 2.013(13) ?
S1A C8 . 1.759(18) ?
S1A C1 . 1.830(19) ?
C1 C2 . 1.392(8) ?
C1 C6 . 1.416(7) ?
C2 C3 . 1.368(9) ?
C3 C4 . 1.396(9) ?
C4 C5 . 1.389(8) ?
C5 C6 . 1.397(9) ?
C6 C7 . 1.455(7) ?
C7 C8 . 1.381(7) ?
C7 C9 . 1.451(7) ?
C9 C14 . 1.398(9) ?
C9 C10 . 1.398(7) ?
C10 C11 . 1.400(8) ?
C11 C12 . 1.368(8) ?
C12 C13 . 1.384(9) ?
C13 C14 . 1.382(7) ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle
_geom_angle_publ_flag
C8 Te1 C1 . . 80.0(2) ?
C8 S1 C10 . . 90.5(3) ?
C8 Te1A C10 . . 76.6(4) ?
C8 S1A C1 . . 95.6(9) ?
C2 C1 C6 . . 121.7(5) ?
C2 C1 S1A . . 133.3(7) ?
C6 C1 S1A . . 105.0(7) ?
C2 C1 Te1 . . 125.1(4) ?
C6 C1 Te1 . . 113.3(4) ?
C3 C2 C1 . . 119.7(5) ?
C2 C3 C4 . . 120.2(5) ?
C5 C4 C3 . . 120.2(6) ?
C4 C5 C6 . . 121.1(6) ?
C5 C6 C1 . . 117.1(5) ?
C5 C6 C7 . . 127.4(5) ?
C1 C6 C7 . . 115.5(5) ?
C8 C7 C9 . . 111.5(5) ?
C8 C7 C6 . . 115.5(5) ?
C9 C7 C6 . . 133.0(5) ?
C7 C8 S1 . . 113.9(4) ?
C7 C8 S1A . . 108.4(7) ?
C7 C8 Te1A . . 120.8(5) ?
S1A C8 Te1A . . 130.8(7) ?
C7 C8 Te1 . . 115.7(4) ?
S1 C8 Te1 . . 130.3(3) ?
C14 C9 C10 . . 117.4(5) ?
C14 C9 C7 . . 130.5(5) ?
C10 C9 C7 . . 112.1(5) ?
C9 C10 C11 . . 122.5(5) ?
C9 C10 S1 . . 111.9(4) ?
C11 C10 S1 . . 125.5(4) ?
C9 C10 Te1A . . 118.9(5) ?
C11 C10 Te1A . . 118.5(5) ?
C12 C11 C10 . . 118.1(5) ?
C11 C12 C13 . . 120.8(6) ?
C14 C13 C12 . . 120.9(6) ?
C13 C14 C9 . . 120.3(5) ?

####################################################################### 
# 
# 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_I
_database_code_depnum_ccdc_archive 'CCDC 1523262'
_audit_update_record             
;
2016-12-18 deposited with the CCDC.
2017-04-07 downloaded from the CCDC.
;
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C25 H22 O2 Te'
_chemical_formula_iupac          ?
_chemical_formula_weight         482.02

_chemical_melting_point          ?

_space_group_crystal_system      monoclinic
_space_group_name_H-M_alt        'P 1 21/n 1'
_space_group_name_Hall           '-P 2yn'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -y-1/2, z-1/2'

_cell_length_a                   17.6341(18)
_cell_length_b                   5.3422(6)
_cell_length_c                   21.002(2)
_cell_angle_alpha                90
_cell_angle_beta                 90.578(2)
_cell_angle_gamma                90
_cell_volume                     1978.4(4)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    2966
_cell_measurement_theta_min      2.3100
_cell_measurement_theta_max      24.4130
_cell_measurement_temperature    103.(2)

_exptl_crystal_description       plate
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.420
_exptl_crystal_size_mid          0.200
_exptl_crystal_size_min          0.040
_exptl_crystal_density_diffrn    1.618
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             960

_exptl_absorpt_coefficient_mu    1.522
_exptl_absorpt_correction_type   Multi-Scan
_exptl_absorpt_process_details   
;
SADABS-2014/5 - Bruker AXS area detector scaling and absorption correction
;
_exptl_absorpt_correction_T_min  0.74
_exptl_absorpt_correction_T_max  0.94

_exptl_special_details           
;
;

_diffrn_ambient_temperature      103.(2)

_diffrn_source                   'fine-focus sealed tube'
_diffrn_source_type              'Bruker KappaCCD'

_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean 8.3333
_diffrn_reflns_number            36444
_diffrn_reflns_av_R_equivalents  0.1142
_diffrn_reflns_av_unetI/netI     0.0764
_diffrn_reflns_theta_min         3.00
_diffrn_reflns_theta_max         29.58
_diffrn_reflns_theta_full        29.58
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measured_fraction_theta_full 0.998
_diffrn_reflns_limit_h_min       -24
_diffrn_reflns_limit_h_max       24
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_l_min       -27
_diffrn_reflns_limit_l_max       29

_reflns_number_total             5549
_reflns_number_gt                3744
_reflns_threshold_expression     'I > 2σ(I)'

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_R_factor_all          0.0795
_refine_ls_R_factor_gt           0.0431
_refine_ls_wR_factor_gt          0.0820
_refine_ls_wR_factor_ref         0.0943
_refine_ls_goodness_of_fit_ref   1.031
_refine_ls_restrained_S_all      1.019
_refine_ls_number_reflns         5549
_refine_ls_number_parameters     291
_refine_ls_number_restraints     144
_refine_ls_number_constraints    ?
_refine_ls_hydrogen_treatment    constr
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0292P)²+0.6408P] where P=(Fo²+2Fc²)/3'

_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?

_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_diff_density_max         0.736
_refine_diff_density_min         -1.371
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?

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'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Te Te -0.5308 1.6751 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_computing_data_collection       'APEX3 (Bruker AXS Inc., 2015)'
_computing_cell_refinement       'SAINT V8.34A (Bruker AXS Inc., 2013)'
_computing_data_reduction        'SAINT V8.34A (Bruker AXS Inc., 2013)'
_computing_structure_solution    'XT, VERSION 2014/4'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    'XP (Bruker AXS Inc., 2015)'
_computing_publication_material  'APEX3 (Bruker AXS Inc., 2015)'

loop_
_atom_site_type_symbol
_atom_site_label
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_calc_flag
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_refinement_flags_posn
_atom_site_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
C C1 0.4606(2) 0.0279(9) 0.80559(18) 0.0294(10) Uani d . . . 1.0 . .
H H1A 0.4322 -0.1217 0.8197 0.035 Uiso calc U . R 1.0 . .
H H1B 0.5097 0.033 0.8288 0.035 Uiso calc U . R 1.0 . .
C C2 0.4169(2) 0.1669(7) 0.71281(18) 0.0196(8) Uani d . . . 1.0 . .
C C3 0.3845(2) 0.3074(8) 0.76007(17) 0.0204(8) Uani d . . . 1.0 . .
C C4 0.3297(2) 0.4847(7) 0.74662(18) 0.0224(8) Uani d . . . 1.0 . .
H H4 0.3074 0.5816 0.7794 0.027 Uiso calc U . R 1.0 . .
C C5 0.3082(2) 0.5166(7) 0.68271(18) 0.0202(8) Uani d . . . 1.0 . .
H H5 0.2708 0.6382 0.6721 0.024 Uiso calc U . R 1.0 . .
C C6 0.3402(2) 0.3747(7) 0.63442(17) 0.0170(8) Uani d . . . 1.0 . .
C C7 0.3967(2) 0.1940(7) 0.64965(17) 0.0171(8) Uani d . . . 1.0 . .
C C8 0.3231(2) 0.3978(7) 0.56618(18) 0.0171(8) Uani d . . . 1.0 . .
C C9 0.2620(2) 0.5797(7) 0.54486(18) 0.0197(8) Uani d . . . 1.0 . .
H H9A 0.2659 0.6063 0.4984 0.024 Uiso calc U . R 1.0 . .
H H9B 0.2705 0.7429 0.5661 0.024 Uiso calc U . R 1.0 . .
C C10 0.1819(2) 0.4853(7) 0.56036(18) 0.0215(8) Uani d . . . 1.0 . .
H H10A 0.1794 0.447 0.6064 0.026 Uiso calc U . R 1.0 . .
H H10B 0.145 0.6207 0.5513 0.026 Uiso calc U . R 1.0 . .
C C11 0.1589(2) 0.2553(8) 0.52318(19) 0.0236(9) Uani d . . . 1.0 . .
H H11A 0.1951 0.1185 0.5329 0.028 Uiso calc U . R 1.0 . .
H H11B 0.1621 0.2922 0.4771 0.028 Uiso calc U . R 1.0 . .
C C12 0.0792(2) 0.1675(9) 0.5383(2) 0.0354(11) Uani d . . . 1.0 . .
H H12A 0.0767 0.1184 0.5832 0.053 Uiso calc U . R 1.0 . .
H H12B 0.0662 0.0237 0.5113 0.053 Uiso calc U . R 1.0 . .
H H12C 0.0432 0.3038 0.53 0.053 Uiso calc U . R 1.0 . .
C C13 0.36302(19) 0.2582(7) 0.52509(18) 0.0166(8) Uani d . . . 1.0 . .
C C14 0.3610(2) 0.2633(7) 0.45450(17) 0.0150(7) Uani d U . . 1.0 . .
C C17 0.3637(2) 0.2676(7) 0.31920(17) 0.0154(7) Uani d U . . 1.0 . .
C C15 0.4117(8) 0.417(3) 0.4221(7) 0.019(2) Uani d U P . 0.47(2) A 1
H H15 0.4452 0.5232 0.4454 0.022 Uiso calc U P R 0.47(2) A 1
C C16 0.4136(8) 0.416(3) 0.3556(7) 0.020(2) Uani d U P . 0.47(2) A 1
H H16 0.4497 0.5174 0.3345 0.024 Uiso calc U P R 0.47(2) A 1
C C18 0.3118(8) 0.117(2) 0.3536(6) 0.018(2) Uani d U P . 0.47(2) A 1
H H18 0.2764 0.0167 0.3307 0.022 Uiso calc U P R 0.47(2) A 1
C C19 0.3114(8) 0.113(2) 0.4195(6) 0.016(2) Uani d U P . 0.47(2) A 1
H H19 0.2769 0.006 0.4411 0.019 Uiso calc U P R 0.47(2) A 1
C C15A 0.3852(7) 0.471(2) 0.4207(5) 0.019(2) Uani d U P . 0.53(2) A 2
H H15A 0.4007 0.6163 0.4433 0.022 Uiso calc U P R 0.53(2) A 2
C C16A 0.3874(7) 0.471(2) 0.3541(6) 0.021(2) Uani d U P . 0.53(2) A 2
H H16A 0.4056 0.6155 0.3325 0.025 Uiso calc U P R 0.53(2) A 2
C C18A 0.3402(8) 0.0587(19) 0.3526(5) 0.018(2) Uani d U P . 0.53(2) A 2
H H18A 0.3243 -0.0861 0.3298 0.022 Uiso calc U P R 0.53(2) A 2
C C19A 0.3392(7) 0.056(2) 0.4184(5) 0.0170(19) Uani d U P . 0.53(2) A 2
H H19A 0.3232 -0.0915 0.4396 0.02 Uiso calc U P R 0.53(2) A 2
C C20 0.3636(2) 0.2690(7) 0.24822(17) 0.0163(8) Uani d . . . 1.0 . .
C C21 0.3237(2) 0.0921(8) 0.2136(2) 0.0290(10) Uani d . . . 1.0 . .
H H21 0.296 -0.0336 0.2354 0.035 Uiso calc U . R 1.0 . .
C C22 0.3232(2) 0.0944(9) 0.14747(19) 0.0299(10) Uani d . . . 1.0 . .
H H22 0.295 -0.0286 0.1247 0.036 Uiso calc U . R 1.0 . .
C C23 0.3631(2) 0.2731(8) 0.11456(19) 0.0247(9) Uani d . . . 1.0 . .
H H23 0.3628 0.274 0.0693 0.03 Uiso calc U . R 1.0 . .
C C24 0.4030(3) 0.4480(8) 0.1478(2) 0.0373(12) Uani d . . . 1.0 . .
H H24 0.4308 0.5719 0.1255 0.045 Uiso calc U . R 1.0 . .
C C25 0.4034(3) 0.4477(8) 0.2146(2) 0.0341(11) Uani d . . . 1.0 . .
H H25 0.4315 0.5719 0.2371 0.041 Uiso calc U . R 1.0 . .
O O1 0.47308(15) 0.0169(5) 0.73804(12) 0.0257(6) Uani d . . . 1.0 . .
O O2 0.41778(16) 0.2505(5) 0.81815(12) 0.0254(6) Uani d . . . 1.0 . .
Te Te1 0.44022(2) 0.01465(5) 0.57095(2) 0.01768(8) Uani d . . . 1.0 . .


_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_site_symmetry_2
_geom_bond_distance
_geom_bond_publ_flag
C1 O2 . 1.435(5) ?
C1 O1 . 1.439(5) ?
C2 C3 . 1.373(5) ?
C2 O1 . 1.376(4) ?
C2 C7 . 1.377(5) ?
C3 C4 . 1.380(5) ?
C3 O2 . 1.382(4) ?
C4 C5 . 1.401(5) ?
C5 C6 . 1.390(5) ?
C6 C7 . 1.421(5) ?
C6 C8 . 1.467(5) ?
C7 Te1 . 2.065(4) ?
C8 C13 . 1.345(5) ?
C8 C9 . 1.516(5) ?
C9 C10 . 1.539(5) ?
C10 C11 . 1.509(5) ?
C11 C12 . 1.519(5) ?
C13 C14 . 1.483(5) ?
C13 Te1 . 2.109(4) ?
C14 C15A . 1.386(12) ?
C14 C19 . 1.393(12) ?
C14 C19A . 1.394(10) ?
C14 C15 . 1.396(13) ?
C17 C16A . 1.375(12) ?
C17 C18A . 1.384(10) ?
C17 C16 . 1.405(14) ?
C17 C18 . 1.420(12) ?
C17 C20 . 1.491(5) ?
C15 C16 . 1.397(19) ?
C18 C19 . 1.385(16) ?
C15A C16A . 1.401(16) ?
C18A C19A . 1.382(14) ?
C20 C21 . 1.381(5) ?
C20 C25 . 1.383(5) ?
C21 C22 . 1.388(6) ?
C22 C23 . 1.376(6) ?
C23 C24 . 1.358(6) ?
C24 C25 . 1.404(6) ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle
_geom_angle_publ_flag
O2 C1 O1 . . 107.5(3) ?
C3 C2 O1 . . 110.1(3) ?
C3 C2 C7 . . 122.2(4) ?
O1 C2 C7 . . 127.6(3) ?
C2 C3 C4 . . 121.5(4) ?
C2 C3 O2 . . 110.0(3) ?
C4 C3 O2 . . 128.4(4) ?
C3 C4 C5 . . 117.5(4) ?
C6 C5 C4 . . 121.6(4) ?
C5 C6 C7 . . 119.7(3) ?
C5 C6 C8 . . 125.9(4) ?
C7 C6 C8 . . 114.4(3) ?
C2 C7 C6 . . 117.5(3) ?
C2 C7 Te1 . . 128.9(3) ?
C6 C7 Te1 . . 113.6(3) ?
C13 C8 C6 . . 118.5(3) ?
C13 C8 C9 . . 122.8(3) ?
C6 C8 C9 . . 118.7(3) ?
C8 C9 C10 . . 112.3(3) ?
C11 C10 C9 . . 113.5(3) ?
C10 C11 C12 . . 112.8(3) ?
C8 C13 C14 . . 128.6(3) ?
C8 C13 Te1 . . 112.9(3) ?
C14 C13 Te1 . . 118.5(2) ?
C15A C14 C19A . . 116.2(7) ?
C19 C14 C15 . . 119.1(8) ?
C15A C14 C13 . . 121.5(5) ?
C19 C14 C13 . . 121.7(6) ?
C19A C14 C13 . . 122.2(5) ?
C15 C14 C13 . . 119.2(7) ?
C16A C17 C18A . . 117.4(7) ?
C16 C17 C18 . . 116.4(8) ?
C16A C17 C20 . . 121.7(6) ?
C18A C17 C20 . . 120.9(5) ?
C16 C17 C20 . . 122.4(6) ?
C18 C17 C20 . . 121.1(6) ?
C14 C15 C16 . . 120.4(10) ?
C15 C16 C17 . . 121.7(10) ?
C19 C18 C17 . . 121.9(9) ?
C18 C19 C14 . . 120.4(9) ?
C14 C15A C16A . . 121.7(9) ?
C17 C16A C15A . . 121.3(9) ?
C19A C18A C17 . . 121.4(8) ?
C18A C19A C14 . . 122.0(8) ?
C21 C20 C25 . . 117.5(4) ?
C21 C20 C17 . . 121.3(3) ?
C25 C20 C17 . . 121.2(3) ?
C20 C21 C22 . . 121.2(4) ?
C23 C22 C21 . . 120.7(4) ?
C24 C23 C22 . . 119.0(4) ?
C23 C24 C25 . . 120.7(4) ?
C20 C25 C24 . . 120.9(4) ?
C2 O1 C1 . . 103.8(3) ?
C3 O2 C1 . . 103.9(3) ?
C7 Te1 C13 . . 80.56(15) ?

