# Electronic Supplementary Material (ESI) for New Journal of Chemistry.
# This journal is © The Royal Society of Chemistry and the Centre National de la Recherche Scientifique 2019

####################################################################### 
# 
# 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_3a_PhO-PhS-Nap
_database_code_depnum_ccdc_archive 'CCDC 1911823'
loop_
_audit_author_name
_audit_author_address
'Satoko Hayashi'
;Wakayama University
Japan
;
_audit_update_record             
;
2019-07-25 deposited with the CCDC.	2019-08-08 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C22 H16 O S'
_chemical_formula_sum            'C22 H16 O S'
_chemical_formula_weight         328.41

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'
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                   8.2047(2)
_cell_length_b                   15.2729(3)
_cell_length_c                   13.0590(3)
_cell_angle_alpha                90
_cell_angle_beta                 92.9933(8)
_cell_angle_gamma                90
_cell_volume                     1634.18(6)
_cell_formula_units_Z            4
_cell_measurement_temperature    103(2)
_cell_measurement_reflns_used    14140
_cell_measurement_theta_min      2.82
_cell_measurement_theta_max      25.5

_exptl_crystal_description       prismatic
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.335
_exptl_crystal_F_000             688
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.300
_exptl_crystal_size_mid          0.200
_exptl_crystal_size_min          0.100
_exptl_absorpt_coefficient_mu    0.203
_shelx_estimated_absorpt_T_min   0.942
_shelx_estimated_absorpt_T_max   0.980
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.942
_exptl_absorpt_correction_T_max  0.980
_exptl_absorpt_process_details   'Jacobson, R. (1998) Private communication'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      103(2)
_diffrn_radiation_wavelength     0.71069
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Rigaku Mercury'
_diffrn_measurement_method       ω
_diffrn_detector_area_resol_mean 7.31
_diffrn_reflns_number            14140
_diffrn_reflns_av_unetI/netI     0.0244
_diffrn_reflns_av_R_equivalents  0.0340
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_theta_min         2.821
_diffrn_reflns_theta_max         25.496
_diffrn_reflns_theta_full        25.240
_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             3020
_reflns_number_gt                2668
_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
_computing_cell_refinement       CrystalClear
_computing_data_reduction        CrystalClear
_computing_structure_solution    'SHELXT-2014/7 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    'Yadokari-XG 2011 (Wakita Nemoto et al., 2011)'
_computing_publication_material  
;Yadokari-XG 2011 (Wakita,Nemoto et al., 2011)
;
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0503P)²+0.8980P] 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         3020
_refine_ls_number_parameters     217
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0404
_refine_ls_R_factor_gt           0.0357
_refine_ls_wR_factor_ref         0.0993
_refine_ls_wR_factor_gt          0.0966
_refine_ls_goodness_of_fit_ref   1.083
_refine_ls_restrained_S_all      1.083
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
S1 S 0.13262(5) -0.09088(3) 0.68400(3) 0.01923(14) Uani 1 1 d . . . . .
C1 C 0.18314(19) -0.16955(10) 0.59061(12) 0.0183(3) Uani 1 1 d . . . . .
C2 C 0.0952(2) -0.17571(11) 0.49649(13) 0.0210(4) Uani 1 1 d . . . . .
H1 H 0.0145 -0.1332 0.4778 0.025 Uiso 1 1 calc R U . . .
C3 C 0.1259(2) -0.24422(11) 0.43015(13) 0.0247(4) Uani 1 1 d . . . . .
H2 H 0.0681 -0.2477 0.3653 0.030 Uiso 1 1 calc R U . . .
C4 C 0.2411(2) -0.30763(11) 0.45856(14) 0.0267(4) Uani 1 1 d . . . . .
H3 H 0.2607 -0.3550 0.4136 0.032 Uiso 1 1 calc R U . . .
C5 C 0.3271(2) -0.30188(11) 0.55211(14) 0.0267(4) Uani 1 1 d . . . . .
H4 H 0.4053 -0.3455 0.5714 0.032 Uiso 1 1 calc R U . . .
C6 C 0.2999(2) -0.23269(11) 0.61808(13) 0.0225(4) Uani 1 1 d . . . . .
H5 H 0.3608 -0.2284 0.6818 0.027 Uiso 1 1 calc R U . . .
C7 C 0.21122(19) 0.00929(10) 0.63551(12) 0.0169(3) Uani 1 1 d . . . . .
C8 C 0.28363(19) 0.01309(11) 0.54270(12) 0.0197(3) Uani 1 1 d . . . . .
H6 H 0.2878 -0.0383 0.5020 0.024 Uiso 1 1 calc R U . . .
C9 C 0.3517(2) 0.09120(11) 0.50659(13) 0.0213(4) Uani 1 1 d . . . . .
H7 H 0.3994 0.0919 0.4418 0.026 Uiso 1 1 calc R U . . .
C10 C 0.34968(19) 0.16571(11) 0.56379(13) 0.0208(4) Uani 1 1 d . . . . .
H8 H 0.3987 0.2176 0.5396 0.025 Uiso 1 1 calc R U . . .
C11 C 0.27455(18) 0.16622(10) 0.65949(12) 0.0178(3) Uani 1 1 d . . . . .
C12 C 0.2699(2) 0.24443(11) 0.71778(13) 0.0217(4) Uani 1 1 d . . . . .
H9 H 0.3214 0.2956 0.6937 0.026 Uiso 1 1 calc R U . . .
C13 C 0.1928(2) 0.24758(11) 0.80788(13) 0.0227(4) Uani 1 1 d . . . . .
H10 H 0.1901 0.3006 0.8458 0.027 Uiso 1 1 calc R U . . .
C14 C 0.1173(2) 0.17185(11) 0.84424(12) 0.0208(4) Uani 1 1 d . . . . .
H11 H 0.0621 0.1740 0.9063 0.025 Uiso 1 1 calc R U . . .
C15 C 0.12313(19) 0.09516(10) 0.79070(12) 0.0173(3) Uani 1 1 d . . . . .
C16 C 0.20138(18) 0.08792(10) 0.69601(12) 0.0162(3) Uani 1 1 d . . . . .
O1 O 0.05685(13) 0.02008(7) 0.83448(8) 0.0190(3) Uani 1 1 d . . . . .
C17 C -0.11347(19) 0.01262(10) 0.83080(12) 0.0175(3) Uani 1 1 d . . . . .
C18 C -0.2122(2) 0.04544(11) 0.75077(12) 0.0220(4) Uani 1 1 d . . . . .
H12 H -0.1664 0.0771 0.6967 0.026 Uiso 1 1 calc R U . . .
C19 C -0.3795(2) 0.03142(11) 0.75069(13) 0.0244(4) Uani 1 1 d . . . . .
H13 H -0.4483 0.0533 0.6958 0.029 Uiso 1 1 calc R U . . .
C20 C -0.4472(2) -0.01428(11) 0.83008(14) 0.0243(4) Uani 1 1 d . . . . .
H14 H -0.5618 -0.0235 0.8297 0.029 Uiso 1 1 calc R U . . .
C21 C -0.3461(2) -0.04637(11) 0.90991(13) 0.0239(4) Uani 1 1 d . . . . .
H15 H -0.3918 -0.0773 0.9646 0.029 Uiso 1 1 calc R U . . .
C22 C -0.1785(2) -0.03355(10) 0.91041(12) 0.0204(3) Uani 1 1 d . . . . .
H16 H -0.1092 -0.0562 0.9647 0.024 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
S1 C1 1.7765(16) . ?
S1 C7 1.7889(16) . ?
C1 C6 1.393(2) . ?
C1 C2 1.396(2) . ?
C2 C3 1.390(2) . ?
C2 H1 0.9500 . ?
C3 C4 1.390(3) . ?
C3 H2 0.9500 . ?
C4 C5 1.381(3) . ?
C4 H3 0.9500 . ?
C5 C6 1.389(2) . ?
C5 H4 0.9500 . ?
C6 H5 0.9500 . ?
C7 C8 1.378(2) . ?
C7 C16 1.442(2) . ?
C8 C9 1.409(2) . ?
C8 H6 0.9500 . ?
C9 C10 1.362(2) . ?
C9 H7 0.9500 . ?
C10 C11 1.422(2) . ?
C10 H8 0.9500 . ?
C11 C12 1.418(2) . ?
C11 C16 1.431(2) . ?
C12 C13 1.366(3) . ?
C12 H9 0.9500 . ?
C13 C14 1.406(2) . ?
C13 H10 0.9500 . ?
C14 C15 1.366(2) . ?
C14 H11 0.9500 . ?
C15 O1 1.4035(19) . ?
C15 C16 1.427(2) . ?
O1 C17 1.4004(19) . ?
C17 C18 1.383(2) . ?
C17 C22 1.386(2) . ?
C18 C19 1.389(2) . ?
C18 H12 0.9500 . ?
C19 C20 1.390(3) . ?
C19 H13 0.9500 . ?
C20 C21 1.388(3) . ?
C20 H14 0.9500 . ?
C21 C22 1.388(2) . ?
C21 H15 0.9500 . ?
C22 H16 0.9500 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C1 S1 C7 103.54(7) . . ?
C6 C1 C2 119.82(15) . . ?
C6 C1 S1 118.25(12) . . ?
C2 C1 S1 121.45(13) . . ?
C3 C2 C1 119.84(15) . . ?
C3 C2 H1 120.1 . . ?
C1 C2 H1 120.1 . . ?
C2 C3 C4 120.06(16) . . ?
C2 C3 H2 120.0 . . ?
C4 C3 H2 120.0 . . ?
C5 C4 C3 120.04(16) . . ?
C5 C4 H3 120.0 . . ?
C3 C4 H3 120.0 . . ?
C4 C5 C6 120.40(16) . . ?
C4 C5 H4 119.8 . . ?
C6 C5 H4 119.8 . . ?
C5 C6 C1 119.83(16) . . ?
C5 C6 H5 120.1 . . ?
C1 C6 H5 120.1 . . ?
C8 C7 C16 119.06(14) . . ?
C8 C7 S1 121.82(12) . . ?
C16 C7 S1 119.12(12) . . ?
C7 C8 C9 121.77(15) . . ?
C7 C8 H6 119.1 . . ?
C9 C8 H6 119.1 . . ?
C10 C9 C8 120.51(15) . . ?
C10 C9 H7 119.7 . . ?
C8 C9 H7 119.7 . . ?
C9 C10 C11 120.32(15) . . ?
C9 C10 H8 119.8 . . ?
C11 C10 H8 119.8 . . ?
C12 C11 C10 120.10(14) . . ?
C12 C11 C16 120.10(15) . . ?
C10 C11 C16 119.80(14) . . ?
C13 C12 C11 121.26(15) . . ?
C13 C12 H9 119.4 . . ?
C11 C12 H9 119.4 . . ?
C12 C13 C14 119.59(15) . . ?
C12 C13 H10 120.2 . . ?
C14 C13 H10 120.2 . . ?
C15 C14 C13 120.31(16) . . ?
C15 C14 H11 119.8 . . ?
C13 C14 H11 119.8 . . ?
C14 C15 O1 117.86(14) . . ?
C14 C15 C16 122.63(14) . . ?
O1 C15 C16 119.41(13) . . ?
C15 C16 C11 116.08(14) . . ?
C15 C16 C7 125.44(14) . . ?
C11 C16 C7 118.48(14) . . ?
C17 O1 C15 117.37(12) . . ?
C18 C17 C22 121.21(15) . . ?
C18 C17 O1 122.74(14) . . ?
C22 C17 O1 115.99(14) . . ?
C17 C18 C19 118.99(16) . . ?
C17 C18 H12 120.5 . . ?
C19 C18 H12 120.5 . . ?
C18 C19 C20 120.69(16) . . ?
C18 C19 H13 119.7 . . ?
C20 C19 H13 119.7 . . ?
C21 C20 C19 119.41(16) . . ?
C21 C20 H14 120.3 . . ?
C19 C20 H14 120.3 . . ?
C20 C21 C22 120.47(16) . . ?
C20 C21 H15 119.8 . . ?
C22 C21 H15 119.8 . . ?
C17 C22 C21 119.22(15) . . ?
C17 C22 H16 120.4 . . ?
C21 C22 H16 120.4 . . ?

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
C7 S1 C1 C6 111.69(13) . . . . ?
C7 S1 C1 C2 -76.27(15) . . . . ?
C6 C1 C2 C3 -0.8(2) . . . . ?
S1 C1 C2 C3 -172.67(13) . . . . ?
C1 C2 C3 C4 1.6(3) . . . . ?
C2 C3 C4 C5 -1.0(3) . . . . ?
C3 C4 C5 C6 -0.4(3) . . . . ?
C4 C5 C6 C1 1.2(3) . . . . ?
C2 C1 C6 C5 -0.6(2) . . . . ?
S1 C1 C6 C5 171.55(13) . . . . ?
C1 S1 C7 C8 2.81(15) . . . . ?
C1 S1 C7 C16 -176.00(12) . . . . ?
C16 C7 C8 C9 1.6(2) . . . . ?
S1 C7 C8 C9 -177.26(12) . . . . ?
C7 C8 C9 C10 0.9(2) . . . . ?
C8 C9 C10 C11 -1.8(2) . . . . ?
C9 C10 C11 C12 -178.73(15) . . . . ?
C9 C10 C11 C16 0.3(2) . . . . ?
C10 C11 C12 C13 177.32(15) . . . . ?
C16 C11 C12 C13 -1.7(2) . . . . ?
C11 C12 C13 C14 0.5(2) . . . . ?
C12 C13 C14 C15 1.0(2) . . . . ?
C13 C14 C15 O1 175.16(14) . . . . ?
C13 C14 C15 C16 -1.2(2) . . . . ?
C14 C15 C16 C11 0.0(2) . . . . ?
O1 C15 C16 C11 -176.32(13) . . . . ?
C14 C15 C16 C7 -179.68(15) . . . . ?
O1 C15 C16 C7 4.0(2) . . . . ?
C12 C11 C16 C15 1.4(2) . . . . ?
C10 C11 C16 C15 -177.60(14) . . . . ?
C12 C11 C16 C7 -178.88(14) . . . . ?
C10 C11 C16 C7 2.1(2) . . . . ?
C8 C7 C16 C15 176.69(15) . . . . ?
S1 C7 C16 C15 -4.5(2) . . . . ?
C8 C7 C16 C11 -3.0(2) . . . . ?
S1 C7 C16 C11 175.84(11) . . . . ?
C14 C15 O1 C17 76.08(17) . . . . ?
C16 C15 O1 C17 -107.41(16) . . . . ?
C15 O1 C17 C18 32.7(2) . . . . ?
C15 O1 C17 C22 -150.15(14) . . . . ?
C22 C17 C18 C19 -0.1(2) . . . . ?
O1 C17 C18 C19 176.86(15) . . . . ?
C17 C18 C19 C20 0.5(3) . . . . ?
C18 C19 C20 C21 -0.2(3) . . . . ?
C19 C20 C21 C22 -0.4(3) . . . . ?
C18 C17 C22 C21 -0.5(2) . . . . ?
O1 C17 C22 C21 -177.68(14) . . . . ?
C20 C21 C22 C17 0.8(2) . . . . ?

_refine_diff_density_max         0.605
_refine_diff_density_min         -0.424
_refine_diff_density_rms         0.061

####################################################################### 
# 
# 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_3e_PhS-PhTe-Nap
_database_code_depnum_ccdc_archive 'CCDC 1911827'
loop_
_audit_author_name
_audit_author_address
'Satoko Hayashi'
;Wakayama University
Japan
;
_audit_update_record             
;
2019-07-25 deposited with the CCDC.	2019-08-08 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C22 H16 S Te'
_chemical_formula_sum            'C22 H16 S Te'
_chemical_formula_weight         440.01

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 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'

_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'

_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                   9.941(2)
_cell_length_b                   11.200(2)
_cell_length_c                   17.991(4)
_cell_angle_alpha                73.943(8)
_cell_angle_beta                 87.143(9)
_cell_angle_gamma                66.842(7)
_cell_volume                     1766.0(7)
_cell_formula_units_Z            4
_cell_measurement_temperature    103(2)
_cell_measurement_reflns_used    5321
_cell_measurement_theta_min      2.4449
_cell_measurement_theta_max      29.1292

_exptl_crystal_description       prism
_exptl_crystal_colour            yellow
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.655
_exptl_crystal_F_000             864
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.250
_exptl_crystal_size_mid          0.150
_exptl_crystal_size_min          0.100
_exptl_absorpt_coefficient_mu    1.802
_shelx_estimated_absorpt_T_min   0.662
_shelx_estimated_absorpt_T_max   0.840
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.662
_exptl_absorpt_correction_T_max  0.840
_exptl_absorpt_process_details   'Jacobson, R. (1998) Private communication'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      103(2)
_diffrn_radiation_wavelength     0.7107
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Rigaku Mercury'
_diffrn_measurement_method       ω
_diffrn_detector_area_resol_mean 7.31
_diffrn_reflns_number            11921
_diffrn_reflns_av_unetI/netI     0.0297
_diffrn_reflns_av_R_equivalents  0.0181
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_theta_min         2.445
_diffrn_reflns_theta_max         25.499
_diffrn_reflns_theta_full        25.241
_diffrn_measured_fraction_theta_max 0.971
_diffrn_measured_fraction_theta_full 0.973
_diffrn_reflns_Laue_measured_fraction_max 0.971
_diffrn_reflns_Laue_measured_fraction_full 0.973
_diffrn_reflns_point_group_measured_fraction_max 0.971
_diffrn_reflns_point_group_measured_fraction_full 0.973
_reflns_number_total             6382
_reflns_number_gt                5744
_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
_computing_cell_refinement       CrystalClear
_computing_data_reduction        CrystalClear
_computing_structure_solution    'SHELXT-2014/7 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    'Yadokari-XG 2011 (Wakita Nemoto et al., 2011)'
_computing_publication_material  
;Yadokari-XG 2011 (Wakita,Nemoto et al., 2011)
;
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+5.6119P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   difmap
_refine_ls_hydrogen_treatment    refall
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         6382
_refine_ls_number_parameters     561
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0368
_refine_ls_R_factor_gt           0.0310
_refine_ls_wR_factor_ref         0.0630
_refine_ls_wR_factor_gt          0.0608
_refine_ls_goodness_of_fit_ref   1.176
_refine_ls_restrained_S_all      1.176
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_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
Te1 Te 1.15557(3) 0.60249(3) -0.37275(2) 0.01610(7) Uani 1 1 d . . . . .
C1 C 1.0966(4) 0.6381(4) -0.4919(2) 0.0146(8) Uani 1 1 d . . . . .
C2 C 1.1598(4) 0.5291(4) -0.5228(2) 0.0172(8) Uani 1 1 d . . . . .
H1 H 1.214(4) 0.439(4) -0.489(2) 0.006(9) Uiso 1 1 d . . . . .
C3 C 1.1438(4) 0.5438(4) -0.6022(2) 0.0205(9) Uani 1 1 d . . . . .
H2 H 1.191(5) 0.471(5) -0.622(3) 0.031(13) Uiso 1 1 d . . . . .
C4 C 1.0666(4) 0.6681(4) -0.6519(2) 0.0189(8) Uani 1 1 d . . . . .
H3 H 1.058(4) 0.676(4) -0.705(2) 0.016(10) Uiso 1 1 d . . . . .
C5 C 0.9963(4) 0.7810(4) -0.6232(2) 0.0155(8) Uani 1 1 d . . . . .
C6 C 0.9140(4) 0.9085(4) -0.6758(2) 0.0210(9) Uani 1 1 d . . . . .
H4 H 0.914(5) 0.914(4) -0.730(3) 0.027(12) Uiso 1 1 d . . . . .
C7 C 0.8428(4) 1.0211(4) -0.6511(2) 0.0205(9) Uani 1 1 d . . . . .
H5 H 0.788(5) 1.105(4) -0.688(2) 0.020(11) Uiso 1 1 d . . . . .
C8 C 0.8455(4) 1.0087(4) -0.5712(2) 0.0197(9) Uani 1 1 d . . . . .
H6 H 0.790(4) 1.083(4) -0.554(2) 0.015(10) Uiso 1 1 d . . . . .
C9 C 0.9207(4) 0.8867(4) -0.5181(2) 0.0162(8) Uani 1 1 d . . . . .
C10 C 1.0063(4) 0.7674(4) -0.5416(2) 0.0138(8) Uani 1 1 d . . . . .
S1 S 0.88999(10) 0.88004(9) -0.41908(6) 0.0160(2) Uani 1 1 d . . . . .
C11 C 1.3370(4) 0.4143(4) -0.3640(2) 0.0164(8) Uani 1 1 d . . . . .
C12 C 1.3267(5) 0.2938(4) -0.3230(2) 0.0240(9) Uani 1 1 d . . . . .
H7 H 1.235(5) 0.293(4) -0.305(3) 0.025(12) Uiso 1 1 d . . . . .
C13 C 1.4457(5) 0.1716(5) -0.3128(3) 0.0277(10) Uani 1 1 d . . . . .
H8 H 1.441(6) 0.091(5) -0.289(3) 0.047(16) Uiso 1 1 d . . . . .
C14 C 1.5772(5) 0.1688(5) -0.3435(3) 0.0277(10) Uani 1 1 d . . . . .
H9 H 1.663(5) 0.082(4) -0.341(2) 0.020(11) Uiso 1 1 d . . . . .
C15 C 1.5885(5) 0.2887(5) -0.3848(3) 0.0248(10) Uani 1 1 d . . . . .
H10 H 1.676(5) 0.285(5) -0.403(3) 0.035(14) Uiso 1 1 d . . . . .
C16 C 1.4695(4) 0.4108(4) -0.3947(2) 0.0205(9) Uani 1 1 d . . . . .
H11 H 1.479(4) 0.492(4) -0.425(2) 0.020(11) Uiso 1 1 d . . . . .
C17 C 0.7397(4) 0.8289(4) -0.4064(2) 0.0159(8) Uani 1 1 d . . . . .
C18 C 0.6619(4) 0.8243(4) -0.4663(2) 0.0174(8) Uani 1 1 d . . . . .
H12 H 0.684(4) 0.848(4) -0.515(2) 0.013(10) Uiso 1 1 d . . . . .
C19 C 0.5467(5) 0.7826(4) -0.4507(2) 0.0209(9) Uani 1 1 d . . . . .
H13 H 0.497(5) 0.779(5) -0.493(3) 0.033(13) Uiso 1 1 d . . . . .
C20 C 0.5072(5) 0.7477(4) -0.3755(3) 0.0220(9) Uani 1 1 d . . . . .
H14 H 0.433(5) 0.722(5) -0.370(3) 0.031(13) Uiso 1 1 d . . . . .
C21 C 0.5835(5) 0.7545(4) -0.3157(2) 0.0219(9) Uani 1 1 d . . . . .
H15 H 0.559(5) 0.727(5) -0.264(3) 0.033(13) Uiso 1 1 d . . . . .
C22 C 0.7002(4) 0.7939(4) -0.3303(2) 0.0189(8) Uani 1 1 d . . . . .
H16 H 0.753(4) 0.791(4) -0.289(2) 0.009(9) Uiso 1 1 d . . . . .
Te2 Te 0.86287(3) 0.78799(2) 0.11041(2) 0.01621(7) Uani 1 1 d . . . . .
C23 C 0.9065(4) 0.8516(4) -0.0091(2) 0.0140(8) Uani 1 1 d . . . . .
C24 C 0.8368(4) 0.9865(4) -0.0473(2) 0.0181(8) Uani 1 1 d . . . . .
H17 H 0.785(4) 1.044(4) -0.020(2) 0.013(10) Uiso 1 1 d . . . . .
C25 C 0.8338(4) 1.0368(4) -0.1282(2) 0.0197(9) Uani 1 1 d . . . . .
H18 H 0.781(5) 1.126(5) -0.150(3) 0.034(13) Uiso 1 1 d . . . . .
C26 C 0.8999(4) 0.9490(4) -0.1713(2) 0.0183(8) Uani 1 1 d . . . . .
H19 H 0.896(4) 0.976(4) -0.225(2) 0.004(9) Uiso 1 1 d . . . . .
C27 C 0.9814(4) 0.8105(4) -0.1354(2) 0.0150(8) Uani 1 1 d . . . . .
C28 C 1.0551(4) 0.7225(4) -0.1806(2) 0.0183(8) Uani 1 1 d . . . . .
H20 H 1.040(5) 0.760(5) -0.235(3) 0.037(14) Uiso 1 1 d . . . . .
C29 C 1.1420(5) 0.5906(4) -0.1484(2) 0.0195(9) Uani 1 1 d . . . . .
H21 H 1.196(5) 0.536(5) -0.178(3) 0.029(12) Uiso 1 1 d . . . . .
C30 C 1.1586(4) 0.5399(4) -0.0672(2) 0.0176(8) Uani 1 1 d . . . . .
H22 H 1.223(5) 0.444(5) -0.039(3) 0.037(14) Uiso 1 1 d . . . . .
C31 C 1.0866(4) 0.6198(4) -0.0202(2) 0.0148(8) Uani 1 1 d . . . . .
C32 C 0.9910(4) 0.7596(4) -0.0522(2) 0.0139(8) Uani 1 1 d . . . . .
S2 S 1.11855(10) 0.54243(9) 0.08133(5) 0.0158(2) Uani 1 1 d . . . . .
C33 C 0.6920(4) 0.9772(4) 0.1109(2) 0.0142(8) Uani 1 1 d . . . . .
C34 C 0.5454(4) 0.9993(4) 0.0984(2) 0.0181(8) Uani 1 1 d . . . . .
H23 H 0.518(4) 0.938(4) 0.085(2) 0.005(9) Uiso 1 1 d . . . . .
C35 C 0.4356(5) 1.1204(4) 0.1031(2) 0.0216(9) Uani 1 1 d . . . . .
H24 H 0.342(6) 1.135(5) 0.091(3) 0.038(14) Uiso 1 1 d . . . . .
C36 C 0.4710(5) 1.2178(4) 0.1206(2) 0.0217(9) Uani 1 1 d . . . . .
H25 H 0.398(5) 1.295(5) 0.122(3) 0.026(12) Uiso 1 1 d . . . . .
C37 C 0.6143(5) 1.1959(4) 0.1341(2) 0.0209(9) Uani 1 1 d . . . . .
H26 H 0.638(5) 1.253(5) 0.152(3) 0.031(13) Uiso 1 1 d . . . . .
C38 C 0.7245(4) 1.0766(4) 0.1292(2) 0.0174(8) Uani 1 1 d . . . . .
H27 H 0.829(5) 1.061(4) 0.141(2) 0.016(10) Uiso 1 1 d . . . . .
C39 C 1.2589(4) 0.5864(4) 0.1081(2) 0.0162(8) Uani 1 1 d . . . . .
C40 C 1.2879(5) 0.5590(4) 0.1872(2) 0.0219(9) Uani 1 1 d . . . . .
H28 H 1.230(5) 0.520(4) 0.225(3) 0.028(12) Uiso 1 1 d . . . . .
C41 C 1.3992(5) 0.5849(4) 0.2131(3) 0.0286(10) Uani 1 1 d . . . . .
H29 H 1.410(5) 0.564(4) 0.265(3) 0.026(12) Uiso 1 1 d . . . . .
C42 C 1.4804(5) 0.6400(4) 0.1620(3) 0.0263(10) Uani 1 1 d . . . . .
H30 H 1.553(5) 0.659(4) 0.180(2) 0.018(11) Uiso 1 1 d . . . . .
C43 C 1.4512(5) 0.6690(4) 0.0824(3) 0.0237(9) Uani 1 1 d . . . . .
H31 H 1.503(5) 0.702(4) 0.049(3) 0.022(12) Uiso 1 1 d . . . . .
C44 C 1.3415(4) 0.6411(4) 0.0552(2) 0.0196(8) Uani 1 1 d . . . . .
H32 H 1.326(4) 0.660(4) 0.002(3) 0.018(11) Uiso 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
Te1 C1 2.136(4) . ?
Te1 C11 2.139(4) . ?
C1 C2 1.390(5) . ?
C1 C10 1.430(5) . ?
C2 C3 1.403(6) . ?
C2 H1 0.98(4) . ?
C3 C4 1.366(6) . ?
C3 H2 0.93(5) . ?
C4 C5 1.409(5) . ?
C4 H3 0.94(4) . ?
C5 C6 1.420(6) . ?
C5 C10 1.438(5) . ?
C6 C7 1.365(6) . ?
C6 H4 0.97(5) . ?
C7 C8 1.406(6) . ?
C7 H5 0.96(4) . ?
C8 C9 1.373(6) . ?
C8 H6 0.93(4) . ?
C9 C10 1.439(5) . ?
C9 S1 1.778(4) . ?
S1 C17 1.783(4) . ?
C11 C12 1.389(6) . ?
C11 C16 1.393(6) . ?
C12 C13 1.384(6) . ?
C12 H7 0.96(5) . ?
C13 C14 1.387(7) . ?
C13 H8 0.91(5) . ?
C14 C15 1.387(6) . ?
C14 H9 1.00(4) . ?
C15 C16 1.384(6) . ?
C15 H10 0.90(5) . ?
C16 H11 0.96(4) . ?
C17 C18 1.381(5) . ?
C17 C22 1.397(5) . ?
C18 C19 1.387(6) . ?
C18 H12 0.88(4) . ?
C19 C20 1.383(6) . ?
C19 H13 0.95(5) . ?
C20 C21 1.384(6) . ?
C20 H14 0.88(5) . ?
C21 C22 1.385(6) . ?
C21 H15 0.95(5) . ?
C22 H16 0.92(4) . ?
Te2 C33 2.134(4) . ?
Te2 C23 2.149(4) . ?
C23 C24 1.373(5) . ?
C23 C32 1.438(5) . ?
C24 C25 1.405(6) . ?
C24 H17 0.90(4) . ?
C25 C26 1.365(6) . ?
C25 H18 0.90(5) . ?
C26 C27 1.410(6) . ?
C26 H19 0.93(4) . ?
C27 C28 1.410(5) . ?
C27 C32 1.440(5) . ?
C28 C29 1.355(6) . ?
C28 H20 0.95(5) . ?
C29 C30 1.406(6) . ?
C29 H21 0.91(5) . ?
C30 C31 1.372(5) . ?
C30 H22 1.00(5) . ?
C31 C32 1.438(5) . ?
C31 S2 1.777(4) . ?
S2 C39 1.777(4) . ?
C33 C38 1.396(5) . ?
C33 C34 1.398(5) . ?
C34 C35 1.388(6) . ?
C34 H23 0.92(4) . ?
C35 C36 1.386(6) . ?
C35 H24 0.91(5) . ?
C36 C37 1.369(6) . ?
C36 H25 0.89(5) . ?
C37 C38 1.378(6) . ?
C37 H26 0.90(5) . ?
C38 H27 1.01(4) . ?
C39 C40 1.390(5) . ?
C39 C44 1.397(6) . ?
C40 C41 1.380(6) . ?
C40 H28 0.99(5) . ?
C41 C42 1.372(7) . ?
C41 H29 0.89(5) . ?
C42 C43 1.396(6) . ?
C42 H30 0.93(4) . ?
C43 C44 1.391(6) . ?
C43 H31 0.87(4) . ?
C44 H32 0.93(4) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C1 Te1 C11 94.96(14) . . ?
C2 C1 C10 119.2(3) . . ?
C2 C1 Te1 116.6(3) . . ?
C10 C1 Te1 124.1(3) . . ?
C1 C2 C3 121.8(4) . . ?
C1 C2 H1 120(2) . . ?
C3 C2 H1 118(2) . . ?
C4 C3 C2 120.2(4) . . ?
C4 C3 H2 119(3) . . ?
C2 C3 H2 120(3) . . ?
C3 C4 C5 120.2(4) . . ?
C3 C4 H3 119(2) . . ?
C5 C4 H3 121(2) . . ?
C4 C5 C6 119.1(4) . . ?
C4 C5 C10 120.6(3) . . ?
C6 C5 C10 120.2(4) . . ?
C7 C6 C5 121.7(4) . . ?
C7 C6 H4 121(3) . . ?
C5 C6 H4 118(3) . . ?
C6 C7 C8 119.0(4) . . ?
C6 C7 H5 119(3) . . ?
C8 C7 H5 122(3) . . ?
C9 C8 C7 121.3(4) . . ?
C9 C8 H6 119(3) . . ?
C7 C8 H6 119(3) . . ?
C8 C9 C10 121.7(4) . . ?
C8 C9 S1 116.2(3) . . ?
C10 C9 S1 121.7(3) . . ?
C1 C10 C5 117.7(3) . . ?
C1 C10 C9 126.5(3) . . ?
C5 C10 C9 115.8(3) . . ?
C9 S1 C17 100.86(18) . . ?
C12 C11 C16 119.0(4) . . ?
C12 C11 Te1 119.9(3) . . ?
C16 C11 Te1 121.0(3) . . ?
C13 C12 C11 120.7(4) . . ?
C13 C12 H7 119(3) . . ?
C11 C12 H7 121(3) . . ?
C12 C13 C14 120.0(4) . . ?
C12 C13 H8 123(3) . . ?
C14 C13 H8 117(3) . . ?
C13 C14 C15 119.7(4) . . ?
C13 C14 H9 122(2) . . ?
C15 C14 H9 118(2) . . ?
C16 C15 C14 120.2(4) . . ?
C16 C15 H10 121(3) . . ?
C14 C15 H10 118(3) . . ?
C15 C16 C11 120.3(4) . . ?
C15 C16 H11 119(3) . . ?
C11 C16 H11 121(3) . . ?
C18 C17 C22 119.8(4) . . ?
C18 C17 S1 124.1(3) . . ?
C22 C17 S1 116.1(3) . . ?
C17 C18 C19 120.0(4) . . ?
C17 C18 H12 121(3) . . ?
C19 C18 H12 119(3) . . ?
C20 C19 C18 120.4(4) . . ?
C20 C19 H13 122(3) . . ?
C18 C19 H13 118(3) . . ?
C19 C20 C21 119.5(4) . . ?
C19 C20 H14 116(3) . . ?
C21 C20 H14 125(3) . . ?
C20 C21 C22 120.6(4) . . ?
C20 C21 H15 119(3) . . ?
C22 C21 H15 120(3) . . ?
C21 C22 C17 119.6(4) . . ?
C21 C22 H16 119(2) . . ?
C17 C22 H16 122(2) . . ?
C33 Te2 C23 95.47(14) . . ?
C24 C23 C32 119.0(3) . . ?
C24 C23 Te2 117.1(3) . . ?
C32 C23 Te2 123.6(3) . . ?
C23 C24 C25 122.5(4) . . ?
C23 C24 H17 119(3) . . ?
C25 C24 H17 119(3) . . ?
C26 C25 C24 119.4(4) . . ?
C26 C25 H18 123(3) . . ?
C24 C25 H18 118(3) . . ?
C25 C26 C27 120.9(4) . . ?
C25 C26 H19 123(2) . . ?
C27 C26 H19 116(2) . . ?
C28 C27 C26 120.2(4) . . ?
C28 C27 C32 120.1(4) . . ?
C26 C27 C32 119.8(4) . . ?
C29 C28 C27 122.1(4) . . ?
C29 C28 H20 121(3) . . ?
C27 C28 H20 116(3) . . ?
C28 C29 C30 118.9(4) . . ?
C28 C29 H21 122(3) . . ?
C30 C29 H21 119(3) . . ?
C31 C30 C29 121.5(4) . . ?
C31 C30 H22 115(3) . . ?
C29 C30 H22 123(3) . . ?
C30 C31 C32 121.3(4) . . ?
C30 C31 S2 116.6(3) . . ?
C32 C31 S2 122.1(3) . . ?
C23 C32 C31 126.2(3) . . ?
C23 C32 C27 117.8(3) . . ?
C31 C32 C27 116.0(3) . . ?
C39 S2 C31 103.74(18) . . ?
C38 C33 C34 119.2(3) . . ?
C38 C33 Te2 120.4(3) . . ?
C34 C33 Te2 120.3(3) . . ?
C35 C34 C33 119.4(4) . . ?
C35 C34 H23 118(2) . . ?
C33 C34 H23 123(2) . . ?
C36 C35 C34 120.2(4) . . ?
C36 C35 H24 122(3) . . ?
C34 C35 H24 118(3) . . ?
C37 C36 C35 120.6(4) . . ?
C37 C36 H25 121(3) . . ?
C35 C36 H25 118(3) . . ?
C36 C37 C38 119.8(4) . . ?
C36 C37 H26 121(3) . . ?
C38 C37 H26 119(3) . . ?
C37 C38 C33 120.8(4) . . ?
C37 C38 H27 119(2) . . ?
C33 C38 H27 120(2) . . ?
C40 C39 C44 119.9(4) . . ?
C40 C39 S2 116.0(3) . . ?
C44 C39 S2 124.1(3) . . ?
C41 C40 C39 119.8(4) . . ?
C41 C40 H28 119(3) . . ?
C39 C40 H28 121(3) . . ?
C42 C41 C40 121.1(4) . . ?
C42 C41 H29 125(3) . . ?
C40 C41 H29 114(3) . . ?
C41 C42 C43 119.5(4) . . ?
C41 C42 H30 120(3) . . ?
C43 C42 H30 120(3) . . ?
C44 C43 C42 120.3(4) . . ?
C44 C43 H31 119(3) . . ?
C42 C43 H31 121(3) . . ?
C43 C44 C39 119.4(4) . . ?
C43 C44 H32 118(3) . . ?
C39 C44 H32 122(3) . . ?

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
C10 C1 C2 C3 3.4(6) . . . . ?
Te1 C1 C2 C3 -172.2(3) . . . . ?
C1 C2 C3 C4 1.1(6) . . . . ?
C2 C3 C4 C5 -3.2(6) . . . . ?
C3 C4 C5 C6 -178.6(4) . . . . ?
C3 C4 C5 C10 0.8(6) . . . . ?
C4 C5 C6 C7 179.5(4) . . . . ?
C10 C5 C6 C7 0.2(6) . . . . ?
C5 C6 C7 C8 -3.1(6) . . . . ?
C6 C7 C8 C9 1.5(6) . . . . ?
C7 C8 C9 C10 3.1(6) . . . . ?
C7 C8 C9 S1 -170.0(3) . . . . ?
C2 C1 C10 C5 -5.6(5) . . . . ?
Te1 C1 C10 C5 169.6(3) . . . . ?
C2 C1 C10 C9 173.1(4) . . . . ?
Te1 C1 C10 C9 -11.7(5) . . . . ?
C4 C5 C10 C1 3.7(5) . . . . ?
C6 C5 C10 C1 -177.0(3) . . . . ?
C4 C5 C10 C9 -175.2(3) . . . . ?
C6 C5 C10 C9 4.2(5) . . . . ?
C8 C9 C10 C1 175.4(4) . . . . ?
S1 C9 C10 C1 -11.8(5) . . . . ?
C8 C9 C10 C5 -5.8(5) . . . . ?
S1 C9 C10 C5 166.9(3) . . . . ?
C8 C9 S1 C17 90.3(3) . . . . ?
C10 C9 S1 C17 -82.8(3) . . . . ?
C16 C11 C12 C13 -0.2(6) . . . . ?
Te1 C11 C12 C13 -176.1(3) . . . . ?
C11 C12 C13 C14 0.1(7) . . . . ?
C12 C13 C14 C15 -0.3(7) . . . . ?
C13 C14 C15 C16 0.6(6) . . . . ?
C14 C15 C16 C11 -0.7(6) . . . . ?
C12 C11 C16 C15 0.5(6) . . . . ?
Te1 C11 C16 C15 176.3(3) . . . . ?
C9 S1 C17 C18 -10.1(4) . . . . ?
C9 S1 C17 C22 170.8(3) . . . . ?
C22 C17 C18 C19 -1.2(6) . . . . ?
S1 C17 C18 C19 179.8(3) . . . . ?
C17 C18 C19 C20 1.1(6) . . . . ?
C18 C19 C20 C21 0.0(6) . . . . ?
C19 C20 C21 C22 -1.0(6) . . . . ?
C20 C21 C22 C17 0.9(6) . . . . ?
C18 C17 C22 C21 0.2(6) . . . . ?
S1 C17 C22 C21 179.3(3) . . . . ?
C32 C23 C24 C25 5.9(6) . . . . ?
Te2 C23 C24 C25 -167.8(3) . . . . ?
C23 C24 C25 C26 1.3(6) . . . . ?
C24 C25 C26 C27 -5.4(6) . . . . ?
C25 C26 C27 C28 -176.7(4) . . . . ?
C25 C26 C27 C32 2.3(6) . . . . ?
C26 C27 C28 C29 175.9(4) . . . . ?
C32 C27 C28 C29 -3.1(6) . . . . ?
C27 C28 C29 C30 0.2(6) . . . . ?
C28 C29 C30 C31 1.5(6) . . . . ?
C29 C30 C31 C32 -0.2(6) . . . . ?
C29 C30 C31 S2 -179.7(3) . . . . ?
C24 C23 C32 C31 170.9(4) . . . . ?
Te2 C23 C32 C31 -15.9(5) . . . . ?
C24 C23 C32 C27 -8.7(5) . . . . ?
Te2 C23 C32 C27 164.5(3) . . . . ?
C30 C31 C32 C23 177.9(4) . . . . ?
S2 C31 C32 C23 -2.7(5) . . . . ?
C30 C31 C32 C27 -2.6(5) . . . . ?
S2 C31 C32 C27 176.9(3) . . . . ?
C28 C27 C32 C23 -176.2(3) . . . . ?
C26 C27 C32 C23 4.8(5) . . . . ?
C28 C27 C32 C31 4.2(5) . . . . ?
C26 C27 C32 C31 -174.8(3) . . . . ?
C30 C31 S2 C39 95.9(3) . . . . ?
C32 C31 S2 C39 -83.6(3) . . . . ?
C38 C33 C34 C35 1.1(6) . . . . ?
Te2 C33 C34 C35 176.6(3) . . . . ?
C33 C34 C35 C36 -0.6(6) . . . . ?
C34 C35 C36 C37 -0.4(6) . . . . ?
C35 C36 C37 C38 0.8(6) . . . . ?
C36 C37 C38 C33 -0.3(6) . . . . ?
C34 C33 C38 C37 -0.7(6) . . . . ?
Te2 C33 C38 C37 -176.2(3) . . . . ?
C31 S2 C39 C40 169.0(3) . . . . ?
C31 S2 C39 C44 -13.1(4) . . . . ?
C44 C39 C40 C41 -0.6(6) . . . . ?
S2 C39 C40 C41 177.4(3) . . . . ?
C39 C40 C41 C42 1.3(6) . . . . ?
C40 C41 C42 C43 -0.7(7) . . . . ?
C41 C42 C43 C44 -0.6(6) . . . . ?
C42 C43 C44 C39 1.3(6) . . . . ?
C40 C39 C44 C43 -0.7(6) . . . . ?
S2 C39 C44 C43 -178.6(3) . . . . ?

_refine_diff_density_max         0.608
_refine_diff_density_min         -0.459
_refine_diff_density_rms         0.089

####################################################################### 
# 
# 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_3d_PhS-PhSe-Nap
_database_code_depnum_ccdc_archive 'CCDC 1911826'
loop_
_audit_author_name
_audit_author_address
'Satoko Hayashi'
;Wakayama University
Japan
;
_audit_update_record             
;
2019-07-25 deposited with the CCDC.	2019-08-08 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C22 H16 S Se'
_chemical_formula_sum            'C22 H16 S Se'
_chemical_formula_weight         391.37

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'
Se Se -0.0929 2.2259 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      orthorhombic
_space_group_IT_number           19
_space_group_name_H-M_alt        'P 21 21 21'
_space_group_name_Hall           'P 2ac 2ab'

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

_cell_length_a                   5.9551(14)
_cell_length_b                   16.121(4)
_cell_length_c                   17.821(4)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     1710.8(7)
_cell_formula_units_Z            4
_cell_measurement_temperature    103(2)
_cell_measurement_reflns_used    5712
_cell_measurement_theta_min      2.5
_cell_measurement_theta_max      25.5

_exptl_crystal_description       prism
_exptl_crystal_colour            yellow
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.519
_exptl_crystal_F_000             792
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.200
_exptl_crystal_size_mid          0.100
_exptl_crystal_size_min          0.100
_exptl_absorpt_coefficient_mu    2.316
_shelx_estimated_absorpt_T_min   0.654
_shelx_estimated_absorpt_T_max   0.801
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.654
_exptl_absorpt_correction_T_max  0.801
_exptl_absorpt_process_details   'Jacobson, R. (1998) Private communication'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      103(2)
_diffrn_radiation_wavelength     0.7107
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Rigaku Mercury'
_diffrn_measurement_method       ω
_diffrn_detector_area_resol_mean 7.31
_diffrn_reflns_number            11625
_diffrn_reflns_av_unetI/netI     0.0359
_diffrn_reflns_av_R_equivalents  0.0262
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_k_min       -19
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_theta_min         2.527
_diffrn_reflns_theta_max         25.500
_diffrn_reflns_theta_full        25.241
_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 0.996
_diffrn_reflns_point_group_measured_fraction_full 0.996
_reflns_number_total             3163
_reflns_number_gt                3076
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.710
_reflns_Friedel_fraction_max     0.996
_reflns_Friedel_fraction_full    0.996

_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
_computing_cell_refinement       CrystalClear
_computing_data_reduction        CrystalClear
_computing_structure_solution    'SHELXT-2014/7 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    'Yadokari-XG 2011 (Wakita Nemoto et al., 2011)'
_computing_publication_material  
;Yadokari-XG 2011 (Wakita,Nemoto et al., 2011)
;
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0259P)²] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   difmap
_refine_ls_hydrogen_treatment    refall
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_abs_structure_details 
;
 Flack x determined using 1240 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.043(4)
_chemical_absolute_configuration ?
_refine_ls_number_reflns         3163
_refine_ls_number_parameters     281
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0233
_refine_ls_R_factor_gt           0.0223
_refine_ls_wR_factor_ref         0.0542
_refine_ls_wR_factor_gt          0.0536
_refine_ls_goodness_of_fit_ref   1.061
_refine_ls_restrained_S_all      1.061
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_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
Se1 Se -0.02930(5) 0.99294(2) 0.35994(2) 0.01723(10) Uani 1 1 d . . . . .
S1 S -0.31186(14) 0.85633(5) 0.29126(5) 0.01229(18) Uani 1 1 d . . . . .
C1 C 0.1383(6) 0.8967(2) 0.39274(18) 0.0128(7) Uani 1 1 d . . . . .
C2 C 0.3050(6) 0.9102(2) 0.44439(19) 0.0161(8) Uani 1 1 d . . . . .
H1 H 0.343(6) 0.967(2) 0.4616(19) 0.013(9) Uiso 1 1 d . . . . .
C3 C 0.4517(6) 0.8464(2) 0.4672(2) 0.0199(8) Uani 1 1 d . . . . .
H2 H 0.573(6) 0.857(2) 0.505(2) 0.020(10) Uiso 1 1 d . . . . .
C4 C 0.4290(6) 0.7688(2) 0.4371(2) 0.0188(8) Uani 1 1 d . . . . .
H3 H 0.532(7) 0.727(2) 0.447(2) 0.027(11) Uiso 1 1 d . . . . .
C5 C 0.2302(6) 0.6700(2) 0.3572(2) 0.0204(8) Uani 1 1 d . . . . .
H4 H 0.324(7) 0.631(2) 0.368(2) 0.033(12) Uiso 1 1 d . . . . .
C6 C 0.0584(8) 0.6490(2) 0.3120(2) 0.0247(9) Uani 1 1 d . . . . .
H5 H 0.041(8) 0.600(3) 0.295(2) 0.040(13) Uiso 1 1 d . . . . .
C7 C -0.1011(7) 0.7085(2) 0.2922(2) 0.0202(8) Uani 1 1 d . . . . .
H6 H -0.219(6) 0.699(2) 0.2621(19) 0.007(9) Uiso 1 1 d . . . . .
C8 C -0.0827(6) 0.7897(2) 0.31614(18) 0.0155(8) Uani 1 1 d . . . . .
C9 C 0.0983(5) 0.81487(19) 0.36368(19) 0.0130(7) Uani 1 1 d . . . . .
C10 C 0.2547(6) 0.7516(2) 0.38620(18) 0.0160(8) Uani 1 1 d . . . . .
C11 C 0.1910(6) 1.0776(2) 0.37823(18) 0.0145(7) Uani 1 1 d . . . . .
C12 C 0.1303(6) 1.1463(2) 0.4216(2) 0.0174(8) Uani 1 1 d . . . . .
H7 H -0.023(6) 1.148(2) 0.4449(19) 0.016(9) Uiso 1 1 d . . . . .
C13 C 0.2758(7) 1.2133(2) 0.4281(2) 0.0207(8) Uani 1 1 d . . . . .
H8 H 0.227(6) 1.260(2) 0.451(2) 0.023(11) Uiso 1 1 d . . . . .
C14 C 0.4811(7) 1.2127(2) 0.3922(2) 0.0208(8) Uani 1 1 d . . . . .
H9 H 0.578(6) 1.259(2) 0.3971(19) 0.013(9) Uiso 1 1 d . . . . .
C15 C 0.5423(6) 1.1451(2) 0.3494(2) 0.0202(8) Uani 1 1 d . . . . .
H10 H 0.691(6) 1.146(2) 0.317(2) 0.018(10) Uiso 1 1 d . . . . .
C16 C 0.3988(6) 1.0775(2) 0.34222(19) 0.0172(8) Uani 1 1 d . . . . .
H11 H 0.445(7) 1.033(2) 0.317(2) 0.023(10) Uiso 1 1 d . . . . .
C17 C -0.2382(6) 0.8913(2) 0.19965(19) 0.0154(7) Uani 1 1 d . . . . .
C18 C -0.0297(7) 0.8801(2) 0.1670(2) 0.0177(8) Uani 1 1 d . . . . .
H12 H 0.069(7) 0.851(2) 0.190(2) 0.025(12) Uiso 1 1 d . . . . .
C19 C 0.0081(7) 0.9069(2) 0.0938(2) 0.0212(8) Uani 1 1 d . . . . .
H13 H 0.144(6) 0.898(2) 0.070(2) 0.020(10) Uiso 1 1 d . . . . .
C20 C -0.1619(7) 0.9460(2) 0.0541(2) 0.0232(9) Uani 1 1 d . . . . .
H14 H -0.138(7) 0.964(2) 0.006(2) 0.028(11) Uiso 1 1 d . . . . .
C21 C -0.3673(7) 0.9592(2) 0.0875(2) 0.0216(8) Uani 1 1 d . . . . .
H15 H -0.489(6) 0.987(2) 0.062(2) 0.018(9) Uiso 1 1 d . . . . .
C22 C -0.4061(6) 0.9325(2) 0.1601(2) 0.0185(8) Uani 1 1 d . . . . .
H16 H -0.538(6) 0.942(2) 0.1808(19) 0.010(9) Uiso 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
Se1 C11 1.921(3) . ?
Se1 C1 1.935(3) . ?
S1 C17 1.782(4) . ?
S1 C8 1.792(4) . ?
C1 C2 1.371(5) . ?
C1 C9 1.437(5) . ?
C2 C3 1.410(5) . ?
C2 H1 0.99(3) . ?
C3 C4 1.367(5) . ?
C3 H2 1.00(4) . ?
C4 C10 1.406(5) . ?
C4 H3 0.92(4) . ?
C5 C6 1.345(6) . ?
C5 C10 1.421(5) . ?
C5 H4 0.86(4) . ?
C6 C7 1.396(6) . ?
C6 H5 0.85(4) . ?
C7 C8 1.381(5) . ?
C7 H6 0.89(3) . ?
C8 C9 1.430(5) . ?
C9 C10 1.438(5) . ?
C11 C16 1.394(5) . ?
C11 C12 1.398(5) . ?
C12 C13 1.390(5) . ?
C12 H7 1.00(4) . ?
C13 C14 1.380(5) . ?
C13 H8 0.91(4) . ?
C14 C15 1.380(5) . ?
C14 H9 0.95(3) . ?
C15 C16 1.391(5) . ?
C15 H10 1.05(4) . ?
C16 H11 0.89(4) . ?
C17 C18 1.383(5) . ?
C17 C22 1.392(5) . ?
C18 C19 1.392(5) . ?
C18 H12 0.85(4) . ?
C19 C20 1.387(6) . ?
C19 H13 0.93(4) . ?
C20 C21 1.377(6) . ?
C20 H14 0.92(4) . ?
C21 C22 1.384(5) . ?
C21 H15 0.97(4) . ?
C22 H16 0.88(4) . ?

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
C11 Se1 C1 99.55(15) . . ?
C17 S1 C8 103.23(16) . . ?
C2 C1 C9 120.5(3) . . ?
C2 C1 Se1 116.7(3) . . ?
C9 C1 Se1 122.8(3) . . ?
C1 C2 C3 121.8(3) . . ?
C1 C2 H1 121.2(19) . . ?
C3 C2 H1 116(2) . . ?
C4 C3 C2 119.5(3) . . ?
C4 C3 H2 120(2) . . ?
C2 C3 H2 121(2) . . ?
C3 C4 C10 120.5(3) . . ?
C3 C4 H3 122(2) . . ?
C10 C4 H3 118(2) . . ?
C6 C5 C10 121.9(4) . . ?
C6 C5 H4 116(3) . . ?
C10 C5 H4 122(3) . . ?
C5 C6 C7 119.8(3) . . ?
C5 C6 H5 123(3) . . ?
C7 C6 H5 117(3) . . ?
C8 C7 C6 121.3(4) . . ?
C8 C7 H6 114(2) . . ?
C6 C7 H6 125(2) . . ?
C7 C8 C9 120.8(3) . . ?
C7 C8 S1 115.5(3) . . ?
C9 C8 S1 123.4(3) . . ?
C8 C9 C1 126.8(3) . . ?
C8 C9 C10 116.9(3) . . ?
C1 C9 C10 116.3(3) . . ?
C4 C10 C5 119.6(3) . . ?
C4 C10 C9 121.2(3) . . ?
C5 C10 C9 119.3(3) . . ?
C16 C11 C12 119.1(3) . . ?
C16 C11 Se1 121.8(3) . . ?
C12 C11 Se1 118.7(3) . . ?
C13 C12 C11 120.0(4) . . ?
C13 C12 H7 121.1(19) . . ?
C11 C12 H7 118.8(19) . . ?
C14 C13 C12 120.6(3) . . ?
C14 C13 H8 120(3) . . ?
C12 C13 H8 119(3) . . ?
C15 C14 C13 119.7(3) . . ?
C15 C14 H9 121(2) . . ?
C13 C14 H9 120(2) . . ?
C14 C15 C16 120.5(3) . . ?
C14 C15 H10 121.1(19) . . ?
C16 C15 H10 118.1(19) . . ?
C15 C16 C11 120.1(3) . . ?
C15 C16 H11 119(3) . . ?
C11 C16 H11 121(3) . . ?
C18 C17 C22 119.6(3) . . ?
C18 C17 S1 124.4(3) . . ?
C22 C17 S1 116.0(3) . . ?
C17 C18 C19 119.9(4) . . ?
C17 C18 H12 119(3) . . ?
C19 C18 H12 121(3) . . ?
C20 C19 C18 120.1(4) . . ?
C20 C19 H13 118(2) . . ?
C18 C19 H13 122(2) . . ?
C21 C20 C19 119.9(4) . . ?
C21 C20 H14 120(3) . . ?
C19 C20 H14 121(3) . . ?
C20 C21 C22 120.3(4) . . ?
C20 C21 H15 122(2) . . ?
C22 C21 H15 118(2) . . ?
C21 C22 C17 120.1(4) . . ?
C21 C22 H16 119(2) . . ?
C17 C22 H16 121(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
C9 C1 C2 C3 4.2(5) . . . . ?
Se1 C1 C2 C3 -174.1(3) . . . . ?
C1 C2 C3 C4 0.3(6) . . . . ?
C2 C3 C4 C10 -2.9(6) . . . . ?
C10 C5 C6 C7 0.4(6) . . . . ?
C5 C6 C7 C8 2.1(6) . . . . ?
C6 C7 C8 C9 -1.5(5) . . . . ?
C6 C7 C8 S1 -175.7(3) . . . . ?
C17 S1 C8 C7 -85.9(3) . . . . ?
C17 S1 C8 C9 100.0(3) . . . . ?
C7 C8 C9 C1 180.0(3) . . . . ?
S1 C8 C9 C1 -6.2(5) . . . . ?
C7 C8 C9 C10 -1.4(5) . . . . ?
S1 C8 C9 C10 172.4(2) . . . . ?
C2 C1 C9 C8 172.8(3) . . . . ?
Se1 C1 C9 C8 -9.1(5) . . . . ?
C2 C1 C9 C10 -5.8(5) . . . . ?
Se1 C1 C9 C10 172.3(2) . . . . ?
C3 C4 C10 C5 -178.2(3) . . . . ?
C3 C4 C10 C9 0.9(5) . . . . ?
C6 C5 C10 C4 175.9(4) . . . . ?
C6 C5 C10 C9 -3.3(5) . . . . ?
C8 C9 C10 C4 -175.5(3) . . . . ?
C1 C9 C10 C4 3.3(5) . . . . ?
C8 C9 C10 C5 3.7(5) . . . . ?
C1 C9 C10 C5 -177.6(3) . . . . ?
C16 C11 C12 C13 0.4(5) . . . . ?
Se1 C11 C12 C13 -171.9(3) . . . . ?
C11 C12 C13 C14 -0.3(5) . . . . ?
C12 C13 C14 C15 0.2(5) . . . . ?
C13 C14 C15 C16 -0.1(5) . . . . ?
C14 C15 C16 C11 0.1(5) . . . . ?
C12 C11 C16 C15 -0.3(5) . . . . ?
Se1 C11 C16 C15 171.8(3) . . . . ?
C8 S1 C17 C18 -11.5(3) . . . . ?
C8 S1 C17 C22 168.6(3) . . . . ?
C22 C17 C18 C19 -2.7(5) . . . . ?
S1 C17 C18 C19 177.5(3) . . . . ?
C17 C18 C19 C20 1.0(5) . . . . ?
C18 C19 C20 C21 0.9(6) . . . . ?
C19 C20 C21 C22 -1.1(6) . . . . ?
C20 C21 C22 C17 -0.7(5) . . . . ?
C18 C17 C22 C21 2.6(5) . . . . ?
S1 C17 C22 C21 -177.6(3) . . . . ?

_refine_diff_density_max         0.312
_refine_diff_density_min         -0.411
_refine_diff_density_rms         0.054

####################################################################### 
# 
# 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_3c_PhO-PhTe-Nap
_database_code_depnum_ccdc_archive 'CCDC 1911825'
loop_
_audit_author_name
_audit_author_address
'Satoko Hayashi'
;Wakayama University
Japan
;
_audit_update_record             
;
2019-07-25 deposited with the CCDC.	2019-08-08 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C22 H16 O Te'
_chemical_formula_weight         423.95

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'

_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'

_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                   9.529(4)
_cell_length_b                   10.002(5)
_cell_length_c                   11.385(5)
_cell_angle_alpha                91.7130(10)
_cell_angle_beta                 113.071(6)
_cell_angle_gamma                117.707(5)
_cell_volume                     853.3(7)
_cell_formula_units_Z            2
_cell_measurement_temperature    93(2)
_cell_measurement_reflns_used    2942
_cell_measurement_theta_min      2.52
_cell_measurement_theta_max      31.18

_exptl_crystal_description       prism
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.650
_exptl_crystal_F_000             416
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.190
_exptl_crystal_size_mid          0.150
_exptl_crystal_size_min          0.060
_exptl_absorpt_coefficient_mu    1.747
_shelx_estimated_absorpt_T_min   0.732
_shelx_estimated_absorpt_T_max   0.902
_exptl_absorpt_correction_type   numerical
_exptl_absorpt_correction_T_min  0.830
_exptl_absorpt_correction_T_max  0.900
_exptl_absorpt_process_details   'NUMABS (Rigaku, 1999)'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      93(2)
_diffrn_radiation_wavelength     0.71075
_diffrn_radiation_type           MoK\a
_diffrn_source                   'Mo K\a'
_diffrn_measurement_device_type  'Rigaku Saturn724'
_diffrn_measurement_method       ω
_diffrn_detector_area_resol_mean 7.111
_diffrn_reflns_number            5359
_diffrn_reflns_av_unetI/netI     0.0235
_diffrn_reflns_av_R_equivalents  0.0241
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_theta_min         3.596
_diffrn_reflns_theta_max         27.478
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.840
_diffrn_measured_fraction_theta_full 0.831
_diffrn_reflns_Laue_measured_fraction_max 0.840
_diffrn_reflns_Laue_measured_fraction_full 0.831
_diffrn_reflns_point_group_measured_fraction_max 0.840
_diffrn_reflns_point_group_measured_fraction_full 0.831
_reflns_number_total             3279
_reflns_number_gt                3224
_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 (Rigaku Inc., 2008)'
_computing_cell_refinement       'CrystalClear (Rigaku Inc., 2008)'
_computing_data_reduction        'CrystalClear (Rigaku Inc., 2008)'
_computing_structure_solution    'SHELXT-2014/7 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    'CrystalStructure 4.0 (Rigaku, 2010)'
_computing_publication_material  'CrystalStructure 4.0 (Rigaku, 2010)'
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0601P)²+1.0124P] 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         3279
_refine_ls_number_parameters     217
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0287
_refine_ls_R_factor_gt           0.0284
_refine_ls_wR_factor_ref         0.0931
_refine_ls_wR_factor_gt          0.0928
_refine_ls_goodness_of_fit_ref   1.158
_refine_ls_restrained_S_all      1.158
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_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
Te1 Te 0.78845(2) 0.59930(2) 0.06472(2) 0.01391(11) Uani 1 1 d . . . . .
O4 O 1.0470(3) 0.7813(3) -0.0071(2) 0.0208(4) Uani 1 1 d . . . . .
C3 C 1.5338(4) 0.9044(3) 0.3071(3) 0.0164(5) Uani 1 1 d . . . . .
H3 H 1.6450 0.9352 0.3804 0.020 Uiso 1 1 calc R U . . .
C5 C 0.6470(4) 0.5003(3) 0.1753(3) 0.0141(5) Uani 1 1 d . . . . .
C6 C 1.2073(4) 0.7812(3) 0.2121(3) 0.0121(5) Uani 1 1 d . . . . .
C7 C 1.0286(4) 0.8043(3) -0.1316(3) 0.0148(5) Uani 1 1 d . . . . .
C8 C 1.3751(4) 0.8290(3) 0.3215(3) 0.0130(5) Uani 1 1 d . . . . .
C9 C 0.6148(4) 0.5917(3) 0.2437(3) 0.0163(5) Uani 1 1 d . . . . .
H9 H 0.6632 0.6995 0.2461 0.020 Uiso 1 1 calc R U . . .
C10 C 1.0637(4) 0.6767(3) 0.3506(3) 0.0147(5) Uani 1 1 d . . . . .
H10 H 0.9592 0.6248 0.3620 0.018 Uiso 1 1 calc R U . . .
C11 C 1.3838(4) 0.8016(3) 0.4451(3) 0.0157(5) Uani 1 1 d . . . . .
H11 H 1.4956 0.8338 0.5183 0.019 Uiso 1 1 calc R U . . .
C12 C 1.2094(4) 0.8186(3) 0.0919(3) 0.0134(5) Uani 1 1 d . . . . .
C13 C 1.2308(4) 0.7287(3) 0.4588(3) 0.0158(5) Uani 1 1 d . . . . .
H13 H 1.2377 0.7130 0.5423 0.019 Uiso 1 1 calc R U . . .
C14 C 0.9930(4) 0.6866(3) -0.2261(3) 0.0185(6) Uani 1 1 d . . . . .
H14 H 0.9916 0.5952 -0.2045 0.022 Uiso 1 1 calc R U . . .
C15 C 0.4709(4) 0.2756(3) 0.2354(3) 0.0168(5) Uani 1 1 d . . . . .
H15 H 0.4202 0.1673 0.2315 0.020 Uiso 1 1 calc R U . . .
C16 C 1.3640(4) 0.8905(3) 0.0798(3) 0.0159(5) Uani 1 1 d . . . . .
H16 H 1.3607 0.9115 -0.0017 0.019 Uiso 1 1 calc R U . . .
C17 C 0.9602(4) 0.8388(4) -0.3847(3) 0.0178(5) Uani 1 1 d . . . . .
H17 H 0.9358 0.8503 -0.4718 0.021 Uiso 1 1 calc R U . . .
C18 C 0.5758(4) 0.3420(3) 0.1725(3) 0.0158(5) Uani 1 1 d . . . . .
H18 H 0.5991 0.2796 0.1274 0.019 Uiso 1 1 calc R U . . .
C19 C 0.5118(4) 0.5253(4) 0.3084(3) 0.0182(5) Uani 1 1 d . . . . .
H19 H 0.4908 0.5881 0.3554 0.022 Uiso 1 1 calc R U . . .
C20 C 0.9971(4) 0.9555(3) -0.2884(3) 0.0188(6) Uani 1 1 d . . . . .
H20 H 0.9986 1.0471 -0.3099 0.023 Uiso 1 1 calc R U . . .
C21 C 1.5283(4) 0.9331(4) 0.1893(3) 0.0174(5) Uani 1 1 d . . . . .
H21 H 1.6351 0.9818 0.1808 0.021 Uiso 1 1 calc R U . . .
C22 C 0.9591(4) 0.7050(4) -0.3533(3) 0.0202(6) Uani 1 1 d . . . . .
H22 H 0.9352 0.6258 -0.4190 0.024 Uiso 1 1 calc R U . . .
C24 C 1.0480(4) 0.6997(3) 0.2274(3) 0.0118(5) Uani 1 1 d . . . . .
C27 C 0.4398(4) 0.3675(4) 0.3044(3) 0.0179(5) Uani 1 1 d . . . . .
H27 H 0.3695 0.3223 0.3486 0.022 Uiso 1 1 calc R U . . .
C28 C 1.0318(4) 0.9393(3) -0.1608(3) 0.0182(6) Uani 1 1 d . . . . .
H28 H 1.0572 1.0191 -0.0948 0.022 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
Te1 C24 2.132(3) . ?
Te1 C5 2.132(3) . ?
O4 C12 1.370(3) . ?
O4 C7 1.399(3) . ?
C3 C21 1.366(4) . ?
C3 C8 1.423(4) . ?
C3 H3 0.9500 . ?
C5 C9 1.393(4) . ?
C5 C18 1.397(4) . ?
C6 C8 1.424(4) . ?
C6 C12 1.435(4) . ?
C6 C24 1.437(4) . ?
C7 C14 1.387(4) . ?
C7 C28 1.389(4) . ?
C8 C11 1.420(4) . ?
C9 C19 1.392(4) . ?
C9 H9 0.9500 . ?
C10 C24 1.389(4) . ?
C10 C13 1.407(4) . ?
C10 H10 0.9500 . ?
C11 C13 1.370(4) . ?
C11 H11 0.9500 . ?
C12 C16 1.373(4) . ?
C13 H13 0.9500 . ?
C14 C22 1.393(4) . ?
C14 H14 0.9500 . ?
C15 C18 1.388(4) . ?
C15 C27 1.393(4) . ?
C15 H15 0.9500 . ?
C16 C21 1.415(4) . ?
C16 H16 0.9500 . ?
C17 C20 1.388(4) . ?
C17 C22 1.392(4) . ?
C17 H17 0.9500 . ?
C18 H18 0.9500 . ?
C19 C27 1.389(4) . ?
C19 H19 0.9500 . ?
C20 C28 1.391(4) . ?
C20 H20 0.9500 . ?
C21 H21 0.9500 . ?
C22 H22 0.9500 . ?
C27 H27 0.9500 . ?
C28 H28 0.9500 . ?

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
C24 Te1 C5 95.73(11) . . ?
C12 O4 C7 120.6(2) . . ?
C21 C3 C8 120.9(3) . . ?
C21 C3 H3 119.6 . . ?
C8 C3 H3 119.6 . . ?
C9 C5 C18 119.6(2) . . ?
C9 C5 Te1 119.7(2) . . ?
C18 C5 Te1 120.5(2) . . ?
C8 C6 C12 116.8(2) . . ?
C8 C6 C24 119.2(2) . . ?
C12 C6 C24 124.0(2) . . ?
C14 C7 C28 121.7(3) . . ?
C14 C7 O4 119.3(3) . . ?
C28 C7 O4 118.8(3) . . ?
C11 C8 C3 120.0(3) . . ?
C11 C8 C6 119.9(3) . . ?
C3 C8 C6 120.1(3) . . ?
C19 C9 C5 120.1(3) . . ?
C19 C9 H9 119.9 . . ?
C5 C9 H9 119.9 . . ?
C24 C10 C13 121.5(3) . . ?
C24 C10 H10 119.3 . . ?
C13 C10 H10 119.3 . . ?
C13 C11 C8 120.0(3) . . ?
C13 C11 H11 120.0 . . ?
C8 C11 H11 120.0 . . ?
O4 C12 C16 123.2(2) . . ?
O4 C12 C6 114.7(2) . . ?
C16 C12 C6 122.1(3) . . ?
C11 C13 C10 120.7(3) . . ?
C11 C13 H13 119.6 . . ?
C10 C13 H13 119.6 . . ?
C7 C14 C22 118.8(3) . . ?
C7 C14 H14 120.6 . . ?
C22 C14 H14 120.6 . . ?
C18 C15 C27 120.2(3) . . ?
C18 C15 H15 119.9 . . ?
C27 C15 H15 119.9 . . ?
C12 C16 C21 119.8(3) . . ?
C12 C16 H16 120.1 . . ?
C21 C16 H16 120.1 . . ?
C20 C17 C22 119.9(3) . . ?
C20 C17 H17 120.0 . . ?
C22 C17 H17 120.0 . . ?
C15 C18 C5 120.1(2) . . ?
C15 C18 H18 119.9 . . ?
C5 C18 H18 119.9 . . ?
C27 C19 C9 120.2(3) . . ?
C27 C19 H19 119.9 . . ?
C9 C19 H19 119.9 . . ?
C17 C20 C28 120.4(3) . . ?
C17 C20 H20 119.8 . . ?
C28 C20 H20 119.8 . . ?
C3 C21 C16 120.3(3) . . ?
C3 C21 H21 119.9 . . ?
C16 C21 H21 119.9 . . ?
C17 C22 C14 120.4(3) . . ?
C17 C22 H22 119.8 . . ?
C14 C22 H22 119.8 . . ?
C10 C24 C6 118.7(2) . . ?
C10 C24 Te1 119.0(2) . . ?
C6 C24 Te1 122.21(19) . . ?
C19 C27 C15 119.8(3) . . ?
C19 C27 H27 120.1 . . ?
C15 C27 H27 120.1 . . ?
C7 C28 C20 118.8(3) . . ?
C7 C28 H28 120.6 . . ?
C20 C28 H28 120.6 . . ?

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
C12 O4 C7 C14 87.8(3) . . . . ?
C12 O4 C7 C28 -97.6(3) . . . . ?
C21 C3 C8 C11 -179.4(3) . . . . ?
C21 C3 C8 C6 0.5(4) . . . . ?
C12 C6 C8 C11 177.4(2) . . . . ?
C24 C6 C8 C11 -2.6(4) . . . . ?
C12 C6 C8 C3 -2.5(3) . . . . ?
C24 C6 C8 C3 177.5(2) . . . . ?
C18 C5 C9 C19 -0.2(4) . . . . ?
Te1 C5 C9 C19 175.5(2) . . . . ?
C3 C8 C11 C13 -179.9(3) . . . . ?
C6 C8 C11 C13 0.2(4) . . . . ?
C7 O4 C12 C16 5.2(4) . . . . ?
C7 O4 C12 C6 -176.8(2) . . . . ?
C8 C6 C12 O4 -175.1(2) . . . . ?
C24 C6 C12 O4 4.9(4) . . . . ?
C8 C6 C12 C16 3.0(4) . . . . ?
C24 C6 C12 C16 -177.0(2) . . . . ?
C8 C11 C13 C10 1.6(4) . . . . ?
C24 C10 C13 C11 -1.1(4) . . . . ?
C28 C7 C14 C22 -0.2(5) . . . . ?
O4 C7 C14 C22 174.3(3) . . . . ?
O4 C12 C16 C21 176.4(3) . . . . ?
C6 C12 C16 C21 -1.5(4) . . . . ?
C27 C15 C18 C5 -1.5(4) . . . . ?
C9 C5 C18 C15 1.2(4) . . . . ?
Te1 C5 C18 C15 -174.4(2) . . . . ?
C5 C9 C19 C27 -0.4(4) . . . . ?
C22 C17 C20 C28 -0.4(5) . . . . ?
C8 C3 C21 C16 1.1(4) . . . . ?
C12 C16 C21 C3 -0.7(4) . . . . ?
C20 C17 C22 C14 0.7(5) . . . . ?
C7 C14 C22 C17 -0.4(5) . . . . ?
C13 C10 C24 C6 -1.3(4) . . . . ?
C13 C10 C24 Te1 174.5(2) . . . . ?
C8 C6 C24 C10 3.0(4) . . . . ?
C12 C6 C24 C10 -176.9(2) . . . . ?
C8 C6 C24 Te1 -172.61(18) . . . . ?
C12 C6 C24 Te1 7.4(3) . . . . ?
C9 C19 C27 C15 0.0(4) . . . . ?
C18 C15 C27 C19 0.9(4) . . . . ?
C14 C7 C28 C20 0.4(5) . . . . ?
O4 C7 C28 C20 -174.1(3) . . . . ?
C17 C20 C28 C7 -0.1(5) . . . . ?

_refine_diff_density_max         1.673
_refine_diff_density_min         -0.889
_refine_diff_density_rms         0.151

####################################################################### 
# 
# 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_3b_PhO-PhSe-Nap
_database_code_depnum_ccdc_archive 'CCDC 1911824'
loop_
_audit_author_name
_audit_author_address
'Satoko Hayashi'
;Wakayama University
Japan
;
_audit_update_record             
;
2019-07-25 deposited with the CCDC.	2019-08-08 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C22 H16 O Se'
_chemical_formula_sum            'C22 H16 O Se'
_chemical_formula_weight         375.31

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'
Se Se -0.0929 2.2259 '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                   8.16210(10)
_cell_length_b                   15.6390(3)
_cell_length_c                   13.0768(3)
_cell_angle_alpha                90
_cell_angle_beta                 92.5953(7)
_cell_angle_gamma                90
_cell_volume                     1667.50(5)
_cell_formula_units_Z            4
_cell_measurement_temperature    103(2)
_cell_measurement_reflns_used    11504
_cell_measurement_theta_min      2.82
_cell_measurement_theta_max      25.49

_exptl_crystal_description       prismatic
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.495
_exptl_crystal_F_000             760
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.250
_exptl_crystal_size_mid          0.200
_exptl_crystal_size_min          0.150
_exptl_absorpt_coefficient_mu    2.256
_shelx_estimated_absorpt_T_min   0.602
_shelx_estimated_absorpt_T_max   0.728
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.602
_exptl_absorpt_correction_T_max  0.728
_exptl_absorpt_process_details   'Jacobson, R. (1998) Private communication'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      103(2)
_diffrn_radiation_wavelength     0.71069
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Rigaku Mercury'
_diffrn_measurement_method       ω
_diffrn_detector_area_resol_mean 7.31
_diffrn_reflns_number            11504
_diffrn_reflns_av_unetI/netI     0.0363
_diffrn_reflns_av_R_equivalents  0.0507
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_theta_min         2.498
_diffrn_reflns_theta_max         25.494
_diffrn_reflns_theta_full        25.240
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 1.000
_diffrn_reflns_point_group_measured_fraction_full 1.000
_reflns_number_total             3092
_reflns_number_gt                2711
_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
_computing_cell_refinement       CrystalClear
_computing_data_reduction        CrystalClear
_computing_structure_solution    'SHELXT-2014/7 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    'Yadokari-XG 2011 (Wakita Nemoto et al., 2011)'
_computing_publication_material  
;Yadokari-XG 2011 (Wakita,Nemoto et al., 2011)
;
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0757P)²+0.2829P] 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         3092
_refine_ls_number_parameters     217
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0437
_refine_ls_R_factor_gt           0.0379
_refine_ls_wR_factor_ref         0.1213
_refine_ls_wR_factor_gt          0.1130
_refine_ls_goodness_of_fit_ref   1.203
_refine_ls_restrained_S_all      1.203
_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
Se1 Se 0.12481(4) -0.09271(2) 0.69061(2) 0.01619(16) Uani 1 1 d . . . . .
C1 C 0.1857(4) -0.17365(19) 0.5886(2) 0.0173(7) Uani 1 1 d . . . . .
C2 C 0.1009(4) -0.1795(2) 0.4941(2) 0.0198(7) Uani 1 1 d . . . . .
H1 H 0.0203 -0.1380 0.4749 0.024 Uiso 1 1 calc R U . . .
C3 C 0.1338(4) -0.2456(2) 0.4282(2) 0.0229(7) Uani 1 1 d . . . . .
H2 H 0.0775 -0.2487 0.3631 0.027 Uiso 1 1 calc R U . . .
C4 C 0.2491(4) -0.3076(2) 0.4566(3) 0.0241(7) Uani 1 1 d . . . . .
H3 H 0.2708 -0.3532 0.4112 0.029 Uiso 1 1 calc R U . . .
C5 C 0.3321(4) -0.3029(2) 0.5509(3) 0.0232(7) Uani 1 1 d . . . . .
H4 H 0.4091 -0.3460 0.5708 0.028 Uiso 1 1 calc R U . . .
C6 C 0.3032(4) -0.2350(2) 0.6170(2) 0.0196(7) Uani 1 1 d . . . . .
H5 H 0.3631 -0.2306 0.6807 0.024 Uiso 1 1 calc R U . . .
C7 C 0.2088(4) 0.01266(19) 0.6360(2) 0.0157(6) Uani 1 1 d . . . . .
C8 C 0.2790(4) 0.0140(2) 0.5422(2) 0.0190(7) Uani 1 1 d . . . . .
H6 H 0.2808 -0.0370 0.5027 0.023 Uiso 1 1 calc R U . . .
C9 C 0.3482(4) 0.08907(19) 0.5036(3) 0.0208(7) Uani 1 1 d . . . . .
H7 H 0.3954 0.0882 0.4385 0.025 Uiso 1 1 calc R U . . .
C10 C 0.3480(4) 0.1636(2) 0.5590(3) 0.0218(7) Uani 1 1 d . . . . .
H8 H 0.3971 0.2137 0.5329 0.026 Uiso 1 1 calc R U . . .
C11 C 0.2742(4) 0.16594(19) 0.6555(2) 0.0169(6) Uani 1 1 d . . . . .
C12 C 0.2727(4) 0.2425(2) 0.7127(3) 0.0219(7) Uani 1 1 d . . . . .
H9 H 0.3235 0.2922 0.6867 0.026 Uiso 1 1 calc R U . . .
C13 C 0.1999(4) 0.2468(2) 0.8046(3) 0.0228(7) Uani 1 1 d . . . . .
H10 H 0.2015 0.2987 0.8423 0.027 Uiso 1 1 calc R U . . .
C14 C 0.1230(4) 0.1745(2) 0.8430(2) 0.0206(7) Uani 1 1 d . . . . .
H11 H 0.0693 0.1780 0.9058 0.025 Uiso 1 1 calc R U . . .
C15 C 0.1246(4) 0.09852(18) 0.7905(2) 0.0160(7) Uani 1 1 d . . . . .
C16 C 0.2011(4) 0.09017(17) 0.6948(2) 0.0154(7) Uani 1 1 d . . . . .
O1 O 0.0577(2) 0.02646(13) 0.83468(15) 0.0165(5) Uani 1 1 d . . . . .
C17 C -0.1135(4) 0.0183(2) 0.8316(2) 0.0164(6) Uani 1 1 d . . . . .
C18 C -0.2122(4) 0.0524(2) 0.7525(2) 0.0204(7) Uani 1 1 d . . . . .
H12 H -0.1663 0.0854 0.7000 0.024 Uiso 1 1 calc R U . . .
C19 C -0.3805(4) 0.0368(2) 0.7522(2) 0.0229(7) Uani 1 1 d . . . . .
H13 H -0.4499 0.0593 0.6985 0.027 Uiso 1 1 calc R U . . .
C20 C -0.4480(4) -0.0107(2) 0.8286(3) 0.0241(7) Uani 1 1 d . . . . .
H14 H -0.5629 -0.0206 0.8276 0.029 Uiso 1 1 calc R U . . .
C21 C -0.3462(4) -0.0439(2) 0.9071(3) 0.0238(7) Uani 1 1 d . . . . .
H15 H -0.3923 -0.0762 0.9602 0.029 Uiso 1 1 calc R U . . .
C22 C -0.1776(4) -0.03035(19) 0.9087(2) 0.0193(7) Uani 1 1 d . . . . .
H16 H -0.1079 -0.0540 0.9615 0.023 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
Se1 C1 1.920(3) . ?
Se1 C7 1.934(3) . ?
C1 C2 1.393(4) . ?
C1 C6 1.395(4) . ?
C2 C3 1.379(4) . ?
C2 H1 0.9500 . ?
C3 C4 1.391(5) . ?
C3 H2 0.9500 . ?
C4 C5 1.381(5) . ?
C4 H3 0.9500 . ?
C5 C6 1.396(5) . ?
C5 H4 0.9500 . ?
C6 H5 0.9500 . ?
C7 C8 1.378(4) . ?
C7 C16 1.439(4) . ?
C8 C9 1.407(4) . ?
C8 H6 0.9500 . ?
C9 C10 1.373(5) . ?
C9 H7 0.9500 . ?
C10 C11 1.423(4) . ?
C10 H8 0.9500 . ?
C11 C12 1.412(4) . ?
C11 C16 1.433(4) . ?
C12 C13 1.366(5) . ?
C12 H9 0.9500 . ?
C13 C14 1.397(5) . ?
C13 H10 0.9500 . ?
C14 C15 1.373(4) . ?
C14 H11 0.9500 . ?
C15 O1 1.389(4) . ?
C15 C16 1.429(5) . ?
O1 C17 1.402(3) . ?
C17 C22 1.384(4) . ?
C17 C18 1.388(4) . ?
C18 C19 1.395(5) . ?
C18 H12 0.9500 . ?
C19 C20 1.379(5) . ?
C19 H13 0.9500 . ?
C20 C21 1.393(5) . ?
C20 H14 0.9500 . ?
C21 C22 1.392(5) . ?
C21 H15 0.9500 . ?
C22 H16 0.9500 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C1 Se1 C7 101.44(13) . . ?
C2 C1 C6 119.9(3) . . ?
C2 C1 Se1 121.8(2) . . ?
C6 C1 Se1 117.7(2) . . ?
C3 C2 C1 120.1(3) . . ?
C3 C2 H1 119.9 . . ?
C1 C2 H1 119.9 . . ?
C2 C3 C4 120.2(3) . . ?
C2 C3 H2 119.9 . . ?
C4 C3 H2 119.9 . . ?
C5 C4 C3 120.0(3) . . ?
C5 C4 H3 120.0 . . ?
C3 C4 H3 120.0 . . ?
C4 C5 C6 120.2(3) . . ?
C4 C5 H4 119.9 . . ?
C6 C5 H4 119.9 . . ?
C1 C6 C5 119.5(3) . . ?
C1 C6 H5 120.2 . . ?
C5 C6 H5 120.2 . . ?
C8 C7 C16 119.6(3) . . ?
C8 C7 Se1 120.7(2) . . ?
C16 C7 Se1 119.7(2) . . ?
C7 C8 C9 121.5(3) . . ?
C7 C8 H6 119.3 . . ?
C9 C8 H6 119.3 . . ?
C10 C9 C8 120.6(3) . . ?
C10 C9 H7 119.7 . . ?
C8 C9 H7 119.7 . . ?
C9 C10 C11 120.0(3) . . ?
C9 C10 H8 120.0 . . ?
C11 C10 H8 120.0 . . ?
C12 C11 C10 120.3(3) . . ?
C12 C11 C16 119.9(3) . . ?
C10 C11 C16 119.8(3) . . ?
C13 C12 C11 121.4(3) . . ?
C13 C12 H9 119.3 . . ?
C11 C12 H9 119.3 . . ?
C12 C13 C14 119.8(3) . . ?
C12 C13 H10 120.1 . . ?
C14 C13 H10 120.1 . . ?
C15 C14 C13 120.4(3) . . ?
C15 C14 H11 119.8 . . ?
C13 C14 H11 119.8 . . ?
C14 C15 O1 118.8(3) . . ?
C14 C15 C16 122.1(3) . . ?
O1 C15 C16 119.0(3) . . ?
C15 C16 C11 116.4(3) . . ?
C15 C16 C7 125.2(3) . . ?
C11 C16 C7 118.4(3) . . ?
C15 O1 C17 118.1(2) . . ?
C22 C17 C18 121.8(3) . . ?
C22 C17 O1 116.0(3) . . ?
C18 C17 O1 122.1(3) . . ?
C17 C18 C19 118.3(3) . . ?
C17 C18 H12 120.9 . . ?
C19 C18 H12 120.9 . . ?
C20 C19 C18 121.2(3) . . ?
C20 C19 H13 119.4 . . ?
C18 C19 H13 119.4 . . ?
C19 C20 C21 119.4(3) . . ?
C19 C20 H14 120.3 . . ?
C21 C20 H14 120.3 . . ?
C22 C21 C20 120.7(3) . . ?
C22 C21 H15 119.6 . . ?
C20 C21 H15 119.6 . . ?
C17 C22 C21 118.7(3) . . ?
C17 C22 H16 120.7 . . ?
C21 C22 H16 120.7 . . ?

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 -0.4(5) . . . . ?
Se1 C1 C2 C3 -171.4(2) . . . . ?
C1 C2 C3 C4 1.4(5) . . . . ?
C2 C3 C4 C5 -0.5(5) . . . . ?
C3 C4 C5 C6 -1.4(5) . . . . ?
C2 C1 C6 C5 -1.4(5) . . . . ?
Se1 C1 C6 C5 169.9(2) . . . . ?
C4 C5 C6 C1 2.3(5) . . . . ?
C16 C7 C8 C9 1.9(5) . . . . ?
Se1 C7 C8 C9 -176.8(2) . . . . ?
C7 C8 C9 C10 0.2(5) . . . . ?
C8 C9 C10 C11 -1.4(5) . . . . ?
C9 C10 C11 C12 -179.6(3) . . . . ?
C9 C10 C11 C16 0.4(5) . . . . ?
C10 C11 C12 C13 178.7(3) . . . . ?
C16 C11 C12 C13 -1.3(4) . . . . ?
C11 C12 C13 C14 -0.8(5) . . . . ?
C12 C13 C14 C15 2.0(5) . . . . ?
C13 C14 C15 O1 175.2(3) . . . . ?
C13 C14 C15 C16 -1.1(5) . . . . ?
C14 C15 C16 C11 -0.9(4) . . . . ?
O1 C15 C16 C11 -177.3(2) . . . . ?
C14 C15 C16 C7 179.5(3) . . . . ?
O1 C15 C16 C7 3.1(4) . . . . ?
C12 C11 C16 C15 2.1(4) . . . . ?
C10 C11 C16 C15 -177.9(3) . . . . ?
C12 C11 C16 C7 -178.3(3) . . . . ?
C10 C11 C16 C7 1.7(4) . . . . ?
C8 C7 C16 C15 176.7(3) . . . . ?
Se1 C7 C16 C15 -4.6(4) . . . . ?
C8 C7 C16 C11 -2.9(4) . . . . ?
Se1 C7 C16 C11 175.8(2) . . . . ?
C14 C15 O1 C17 77.6(3) . . . . ?
C16 C15 O1 C17 -105.9(3) . . . . ?
C15 O1 C17 C22 -153.7(3) . . . . ?
C15 O1 C17 C18 30.2(4) . . . . ?
C22 C17 C18 C19 0.3(5) . . . . ?
O1 C17 C18 C19 176.2(3) . . . . ?
C17 C18 C19 C20 0.4(5) . . . . ?
C18 C19 C20 C21 -0.3(5) . . . . ?
C19 C20 C21 C22 -0.6(5) . . . . ?
C18 C17 C22 C21 -1.1(5) . . . . ?
O1 C17 C22 C21 -177.2(3) . . . . ?
C20 C21 C22 C17 1.2(5) . . . . ?

_refine_diff_density_max         1.027
_refine_diff_density_min         -1.000
_refine_diff_density_rms         0.274

####################################################################### 
# 
# 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_3f_PhSe-PhTe-Nap
_database_code_depnum_ccdc_archive 'CCDC 1911828'
loop_
_audit_author_name
_audit_author_address
'Satoko Hayashi'
;Wakayama University
Japan
;
_audit_update_record             
;
2019-07-25 deposited with the CCDC.	2019-08-08 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C22 H16 Se Te'
_chemical_formula_weight         486.91

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'
Se Se -0.0929 2.2259 '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'

_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'

_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                   10.0676(4)
_cell_length_b                   11.2431(4)
_cell_length_c                   18.0510(8)
_cell_angle_alpha                73.8950(10)
_cell_angle_beta                 86.942(2)
_cell_angle_gamma                67.0670(10)
_cell_volume                     1804.41(13)
_cell_formula_units_Z            4
_cell_measurement_temperature    110(2)
_cell_measurement_reflns_used    9673
_cell_measurement_theta_min      2.43
_cell_measurement_theta_max      27.50

_exptl_crystal_description       block
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.792
_exptl_crystal_F_000             936
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.100
_exptl_crystal_size_mid          0.100
_exptl_crystal_size_min          0.100
_exptl_absorpt_coefficient_mu    3.665
_shelx_estimated_absorpt_T_min   0.711
_shelx_estimated_absorpt_T_max   0.711
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.4887
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_process_details   SADABS
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      110(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 10.42
_diffrn_reflns_number            51618
_diffrn_reflns_av_unetI/netI     0.0188
_diffrn_reflns_av_R_equivalents  0.0292
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_theta_min         2.349
_diffrn_reflns_theta_max         27.485
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.991
_diffrn_measured_fraction_theta_full 0.992
_diffrn_reflns_Laue_measured_fraction_max 0.991
_diffrn_reflns_Laue_measured_fraction_full 0.992
_diffrn_reflns_point_group_measured_fraction_max 0.991
_diffrn_reflns_point_group_measured_fraction_full 0.992
_reflns_number_total             8203
_reflns_number_gt                7770
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;

_computing_data_collection       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick 2008)'
_computing_structure_refinement  'SHELXL-2014 (Sheldrick 2014)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0184P)²+1.0970P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ShelxT
_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         8203
_refine_ls_number_parameters     433
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0234
_refine_ls_R_factor_gt           0.0215
_refine_ls_wR_factor_ref         0.0527
_refine_ls_wR_factor_gt          0.0516
_refine_ls_goodness_of_fit_ref   1.327
_refine_ls_restrained_S_all      1.327
_refine_ls_shift/su_max          0.003
_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
Te1 Te 0.34495(2) 0.39535(2) 0.87401(2) 0.01841(4) Uani 1 1 d . . . . .
C1 C 0.4039(2) 0.3610(2) 0.99255(12) 0.0162(4) Uani 1 1 d . . . . .
C2 C 0.3414(2) 0.4696(2) 1.02190(13) 0.0206(4) Uani 1 1 d . . . . .
H2A H 0.2861 0.5550 0.9878 0.025 Uiso 1 1 calc R U . . .
C3 C 0.3569(2) 0.4583(2) 1.10099(13) 0.0240(5) Uani 1 1 d . . . . .
H3A H 0.3140 0.5355 1.1194 0.029 Uiso 1 1 calc R U . . .
C4 C 0.4336(2) 0.3363(2) 1.15091(13) 0.0242(5) Uani 1 1 d . . . . .
H4A H 0.4400 0.3277 1.2046 0.029 Uiso 1 1 calc R U . . .
C5 C 0.5035(2) 0.2226(2) 1.12348(12) 0.0185(4) Uani 1 1 d . . . . .
C6 C 0.5860(2) 0.0977(2) 1.17688(13) 0.0234(5) Uani 1 1 d . . . . .
H6A H 0.5907 0.0924 1.2302 0.028 Uiso 1 1 calc R U . . .
C7 C 0.6582(2) -0.0145(2) 1.15351(14) 0.0261(5) Uani 1 1 d . . . . .
H7A H 0.7103 -0.0979 1.1902 0.031 Uiso 1 1 calc R U . . .
C8 C 0.6551(2) -0.0057(2) 1.07447(14) 0.0226(4) Uani 1 1 d . . . . .
H8A H 0.7070 -0.0836 1.0579 0.027 Uiso 1 1 calc R U . . .
C9 C 0.5785(2) 0.1133(2) 1.02068(12) 0.0172(4) Uani 1 1 d . . . . .
C10 C 0.4937(2) 0.2331(2) 1.04264(12) 0.0150(4) Uani 1 1 d . . . . .
Se1 Se 0.61292(2) 0.11185(2) 0.91534(2) 0.01840(5) Uani 1 1 d . . . . .
C11 C 0.1652(2) 0.5815(2) 0.86526(12) 0.0196(4) Uani 1 1 d . . . . .
C12 C 0.0349(2) 0.5848(3) 0.89648(13) 0.0236(5) Uani 1 1 d . . . . .
H12A H 0.0268 0.5037 0.9257 0.028 Uiso 1 1 calc R U . . .
C13 C -0.0834(3) 0.7065(3) 0.88507(15) 0.0311(6) Uani 1 1 d . . . . .
H13A H -0.1721 0.7084 0.9067 0.037 Uiso 1 1 calc R U . . .
C14 C -0.0724(3) 0.8253(3) 0.84219(15) 0.0360(6) Uani 1 1 d . . . . .
H14A H -0.1538 0.9081 0.8340 0.043 Uiso 1 1 calc R U . . .
C15 C 0.0570(3) 0.8231(3) 0.81143(16) 0.0379(6) Uani 1 1 d . . . . .
H15A H 0.0649 0.9045 0.7827 0.046 Uiso 1 1 calc R U . . .
C16 C 0.1758(3) 0.7013(2) 0.82270(14) 0.0288(5) Uani 1 1 d . . . . .
H16A H 0.2644 0.6999 0.8013 0.035 Uiso 1 1 calc R U . . .
C17 C 0.7709(2) 0.1701(2) 0.90348(12) 0.0165(4) Uani 1 1 d . . . . .
C18 C 0.8124(3) 0.2068(2) 0.82868(13) 0.0233(5) Uani 1 1 d . . . . .
H18A H 0.7628 0.2036 0.7864 0.028 Uiso 1 1 calc R U . . .
C19 C 0.9269(3) 0.2483(3) 0.81608(14) 0.0279(5) Uani 1 1 d . . . . .
H19A H 0.9566 0.2719 0.7651 0.034 Uiso 1 1 calc R U . . .
C20 C 0.9979(2) 0.2554(2) 0.87719(15) 0.0265(5) Uani 1 1 d . . . . .
H20A H 1.0742 0.2864 0.8681 0.032 Uiso 1 1 calc R U . . .
C21 C 0.9574(2) 0.2173(3) 0.95138(14) 0.0261(5) Uani 1 1 d . . . . .
H21A H 1.0075 0.2207 0.9934 0.031 Uiso 1 1 calc R U . . .
C22 C 0.8442(2) 0.1741(2) 0.96531(13) 0.0216(4) Uani 1 1 d . . . . .
H22A H 0.8172 0.1476 1.0166 0.026 Uiso 1 1 calc R U . . .
Te2 Te 0.36228(2) 0.78814(2) 0.60958(2) 0.01873(4) Uani 1 1 d . . . . .
C23 C 0.4061(2) 0.8504(2) 0.49054(12) 0.0165(4) Uani 1 1 d . . . . .
C24 C 0.3354(2) 0.9853(2) 0.45276(13) 0.0223(4) Uani 1 1 d . . . . .
H24A H 0.2865 1.0459 0.4823 0.027 Uiso 1 1 calc R U . . .
C25 C 0.3333(2) 1.0358(2) 0.37245(14) 0.0252(5) Uani 1 1 d . . . . .
H25A H 0.2856 1.1295 0.3486 0.030 Uiso 1 1 calc R U . . .
C26 C 0.3995(2) 0.9509(2) 0.32861(13) 0.0216(4) Uani 1 1 d . . . . .
H26A H 0.3911 0.9843 0.2739 0.026 Uiso 1 1 calc R U . . .
C27 C 0.4808(2) 0.8130(2) 0.36426(12) 0.0170(4) Uani 1 1 d . . . . .
C28 C 0.5564(2) 0.7281(2) 0.31744(13) 0.0225(5) Uani 1 1 d . . . . .
H28A H 0.5461 0.7638 0.2628 0.027 Uiso 1 1 calc R U . . .
C29 C 0.6431(3) 0.5970(3) 0.34910(14) 0.0263(5) Uani 1 1 d . . . . .
H29A H 0.6930 0.5416 0.3169 0.032 Uiso 1 1 calc R U . . .
C30 C 0.6584(2) 0.5439(2) 0.42992(14) 0.0231(5) Uani 1 1 d . . . . .
H30A H 0.7205 0.4526 0.4521 0.028 Uiso 1 1 calc R U . . .
C31 C 0.5849(2) 0.6218(2) 0.47741(12) 0.0173(4) Uani 1 1 d . . . . .
C32 C 0.4897(2) 0.7606(2) 0.44692(12) 0.0153(4) Uani 1 1 d . . . . .
Se2 Se 0.62098(2) 0.53291(2) 0.58587(2) 0.01884(5) Uani 1 1 d . . . . .
C33 C 0.1933(2) 0.9761(2) 0.61028(12) 0.0172(4) Uani 1 1 d . . . . .
C34 C 0.0492(2) 0.9980(2) 0.59867(13) 0.0227(5) Uani 1 1 d . . . . .
H34A H 0.0251 0.9316 0.5864 0.027 Uiso 1 1 calc R U . . .
C35 C -0.0597(2) 1.1172(3) 0.60507(14) 0.0283(5) Uani 1 1 d . . . . .
H35A H -0.1581 1.1325 0.5966 0.034 Uiso 1 1 calc R U . . .
C36 C -0.0250(3) 1.2131(3) 0.62365(14) 0.0283(5) Uani 1 1 d . . . . .
H36A H -0.0998 1.2941 0.6281 0.034 Uiso 1 1 calc R U . . .
C37 C 0.1181(3) 1.1921(2) 0.63580(13) 0.0244(5) Uani 1 1 d . . . . .
H37A H 0.1414 1.2584 0.6486 0.029 Uiso 1 1 calc R U . . .
C38 C 0.2277(2) 1.0734(2) 0.62913(12) 0.0198(4) Uani 1 1 d . . . . .
H38A H 0.3259 1.0586 0.6374 0.024 Uiso 1 1 calc R U . . .
C39 C 0.7694(2) 0.5861(2) 0.61004(12) 0.0181(4) Uani 1 1 d . . . . .
C40 C 0.8478(2) 0.6398(2) 0.55510(13) 0.0237(5) Uani 1 1 d . . . . .
H40A H 0.8276 0.6548 0.5017 0.028 Uiso 1 1 calc R U . . .
C41 C 0.9558(3) 0.6714(3) 0.57866(16) 0.0320(5) Uani 1 1 d . . . . .
H41A H 1.0079 0.7102 0.5411 0.038 Uiso 1 1 calc R U . . .
C42 C 0.9883(3) 0.6469(3) 0.65637(17) 0.0354(6) Uani 1 1 d . . . . .
H42A H 1.0631 0.6680 0.6721 0.042 Uiso 1 1 calc R U . . .
C43 C 0.9117(3) 0.5920(3) 0.71064(15) 0.0376(7) Uani 1 1 d . . . . .
H43A H 0.9347 0.5741 0.7640 0.045 Uiso 1 1 calc R U . . .
C44 C 0.8008(3) 0.5624(2) 0.68822(13) 0.0287(5) Uani 1 1 d . . . . .
H44A H 0.7470 0.5262 0.7260 0.034 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
Te1 C11 2.139(2) . ?
Te1 C1 2.140(2) . ?
C1 C2 1.376(3) . ?
C1 C10 1.433(3) . ?
C2 C3 1.409(3) . ?
C3 C4 1.361(3) . ?
C4 C5 1.409(3) . ?
C5 C6 1.420(3) . ?
C5 C10 1.437(3) . ?
C6 C7 1.358(4) . ?
C7 C8 1.404(3) . ?
C8 C9 1.372(3) . ?
C9 C10 1.437(3) . ?
C9 Se1 1.918(2) . ?
Se1 C17 1.924(2) . ?
C11 C12 1.390(3) . ?
C11 C16 1.395(3) . ?
C12 C13 1.391(3) . ?
C13 C14 1.388(4) . ?
C14 C15 1.382(4) . ?
C15 C16 1.393(4) . ?
C17 C18 1.390(3) . ?
C17 C22 1.391(3) . ?
C18 C19 1.389(3) . ?
C19 C20 1.383(4) . ?
C20 C21 1.379(3) . ?
C21 C22 1.390(3) . ?
Te2 C33 2.138(2) . ?
Te2 C23 2.146(2) . ?
C23 C24 1.382(3) . ?
C23 C32 1.434(3) . ?
C24 C25 1.401(3) . ?
C25 C26 1.359(3) . ?
C26 C27 1.415(3) . ?
C27 C28 1.420(3) . ?
C27 C32 1.438(3) . ?
C28 C29 1.358(3) . ?
C29 C30 1.406(3) . ?
C30 C31 1.376(3) . ?
C31 C32 1.439(3) . ?
C31 Se2 1.916(2) . ?
Se2 C39 1.921(2) . ?
C33 C34 1.391(3) . ?
C33 C38 1.395(3) . ?
C34 C35 1.392(3) . ?
C35 C36 1.380(4) . ?
C36 C37 1.386(3) . ?
C37 C38 1.393(3) . ?
C39 C40 1.388(3) . ?
C39 C44 1.391(3) . ?
C40 C41 1.387(3) . ?
C41 C42 1.384(4) . ?
C42 C43 1.375(4) . ?
C43 C44 1.390(4) . ?

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
C11 Te1 C1 95.22(8) . . ?
C2 C1 C10 119.55(19) . . ?
C2 C1 Te1 115.76(15) . . ?
C10 C1 Te1 124.54(15) . . ?
C1 C2 C3 122.1(2) . . ?
C4 C3 C2 119.7(2) . . ?
C3 C4 C5 120.4(2) . . ?
C4 C5 C6 119.0(2) . . ?
C4 C5 C10 120.7(2) . . ?
C6 C5 C10 120.4(2) . . ?
C7 C6 C5 121.5(2) . . ?
C6 C7 C8 119.2(2) . . ?
C9 C8 C7 121.3(2) . . ?
C8 C9 C10 121.8(2) . . ?
C8 C9 Se1 114.74(16) . . ?
C10 C9 Se1 123.04(15) . . ?
C1 C10 C5 117.32(19) . . ?
C1 C10 C9 127.01(19) . . ?
C5 C10 C9 115.66(19) . . ?
C9 Se1 C17 98.05(9) . . ?
C12 C11 C16 119.3(2) . . ?
C12 C11 Te1 121.37(17) . . ?
C16 C11 Te1 119.15(17) . . ?
C11 C12 C13 120.1(2) . . ?
C14 C13 C12 120.2(2) . . ?
C15 C14 C13 120.0(2) . . ?
C14 C15 C16 119.9(3) . . ?
C15 C16 C11 120.4(2) . . ?
C18 C17 C22 120.1(2) . . ?
C18 C17 Se1 116.59(16) . . ?
C22 C17 Se1 123.27(16) . . ?
C19 C18 C17 119.6(2) . . ?
C20 C19 C18 120.4(2) . . ?
C21 C20 C19 119.7(2) . . ?
C20 C21 C22 120.7(2) . . ?
C21 C22 C17 119.4(2) . . ?
C33 Te2 C23 95.77(8) . . ?
C24 C23 C32 118.89(19) . . ?
C24 C23 Te2 116.18(15) . . ?
C32 C23 Te2 124.58(15) . . ?
C23 C24 C25 122.3(2) . . ?
C26 C25 C24 120.1(2) . . ?
C25 C26 C27 120.2(2) . . ?
C26 C27 C28 119.1(2) . . ?
C26 C27 C32 120.29(19) . . ?
C28 C27 C32 120.59(19) . . ?
C29 C28 C27 121.4(2) . . ?
C28 C29 C30 119.4(2) . . ?
C31 C30 C29 121.1(2) . . ?
C30 C31 C32 121.8(2) . . ?
C30 C31 Se2 115.23(16) . . ?
C32 C31 Se2 122.99(15) . . ?
C23 C32 C31 126.64(19) . . ?
C23 C32 C27 117.73(18) . . ?
C31 C32 C27 115.62(18) . . ?
C31 Se2 C39 100.50(9) . . ?
C34 C33 C38 119.6(2) . . ?
C34 C33 Te2 120.81(17) . . ?
C38 C33 Te2 119.31(15) . . ?
C35 C34 C33 119.9(2) . . ?
C36 C35 C34 120.1(2) . . ?
C35 C36 C37 120.4(2) . . ?
C36 C37 C38 119.8(2) . . ?
C37 C38 C33 120.1(2) . . ?
C40 C39 C44 120.0(2) . . ?
C40 C39 Se2 123.98(16) . . ?
C44 C39 Se2 115.96(18) . . ?
C39 C40 C41 119.6(2) . . ?
C42 C41 C40 120.7(3) . . ?
C43 C42 C41 119.6(2) . . ?
C42 C43 C44 120.7(2) . . ?
C43 C44 C39 119.5(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
C10 C1 C2 C3 -3.2(3) . . . . ?
Te1 C1 C2 C3 172.62(18) . . . . ?
C1 C2 C3 C4 -1.2(4) . . . . ?
C2 C3 C4 C5 3.1(4) . . . . ?
C3 C4 C5 C6 178.2(2) . . . . ?
C3 C4 C5 C10 -0.7(3) . . . . ?
C4 C5 C6 C7 -178.5(2) . . . . ?
C10 C5 C6 C7 0.4(3) . . . . ?
C5 C6 C7 C8 2.1(4) . . . . ?
C6 C7 C8 C9 -1.1(4) . . . . ?
C7 C8 C9 C10 -2.3(3) . . . . ?
C7 C8 C9 Se1 170.29(17) . . . . ?
C2 C1 C10 C5 5.4(3) . . . . ?
Te1 C1 C10 C5 -170.03(15) . . . . ?
C2 C1 C10 C9 -173.3(2) . . . . ?
Te1 C1 C10 C9 11.3(3) . . . . ?
C4 C5 C10 C1 -3.5(3) . . . . ?
C6 C5 C10 C1 177.57(19) . . . . ?
C4 C5 C10 C9 175.3(2) . . . . ?
C6 C5 C10 C9 -3.6(3) . . . . ?
C8 C9 C10 C1 -176.7(2) . . . . ?
Se1 C9 C10 C1 11.3(3) . . . . ?
C8 C9 C10 C5 4.6(3) . . . . ?
Se1 C9 C10 C5 -167.42(15) . . . . ?
C16 C11 C12 C13 0.2(3) . . . . ?
Te1 C11 C12 C13 -175.28(16) . . . . ?
C11 C12 C13 C14 0.3(3) . . . . ?
C12 C13 C14 C15 -0.8(4) . . . . ?
C13 C14 C15 C16 0.8(4) . . . . ?
C14 C15 C16 C11 -0.4(4) . . . . ?
C12 C11 C16 C15 -0.1(4) . . . . ?
Te1 C11 C16 C15 175.43(19) . . . . ?
C22 C17 C18 C19 -0.4(3) . . . . ?
Se1 C17 C18 C19 -179.22(18) . . . . ?
C17 C18 C19 C20 -1.1(4) . . . . ?
C18 C19 C20 C21 1.9(4) . . . . ?
C19 C20 C21 C22 -1.2(4) . . . . ?
C20 C21 C22 C17 -0.3(4) . . . . ?
C18 C17 C22 C21 1.1(3) . . . . ?
Se1 C17 C22 C21 179.85(17) . . . . ?
C32 C23 C24 C25 5.0(3) . . . . ?
Te2 C23 C24 C25 -168.49(18) . . . . ?
C23 C24 C25 C26 1.6(4) . . . . ?
C24 C25 C26 C27 -5.2(4) . . . . ?
C25 C26 C27 C28 -176.0(2) . . . . ?
C25 C26 C27 C32 2.3(3) . . . . ?
C26 C27 C28 C29 175.8(2) . . . . ?
C32 C27 C28 C29 -2.4(3) . . . . ?
C27 C28 C29 C30 0.1(4) . . . . ?
C28 C29 C30 C31 1.2(4) . . . . ?
C29 C30 C31 C32 -0.1(3) . . . . ?
C29 C30 C31 Se2 -179.28(18) . . . . ?
C24 C23 C32 C31 171.3(2) . . . . ?
Te2 C23 C32 C31 -15.7(3) . . . . ?
C24 C23 C32 C27 -7.7(3) . . . . ?
Te2 C23 C32 C27 165.27(14) . . . . ?
C30 C31 C32 C23 178.9(2) . . . . ?
Se2 C31 C32 C23 -2.0(3) . . . . ?
C30 C31 C32 C27 -2.1(3) . . . . ?
Se2 C31 C32 C27 176.98(14) . . . . ?
C26 C27 C32 C23 4.2(3) . . . . ?
C28 C27 C32 C23 -177.55(19) . . . . ?
C26 C27 C32 C31 -174.94(19) . . . . ?
C28 C27 C32 C31 3.3(3) . . . . ?
C38 C33 C34 C35 0.7(3) . . . . ?
Te2 C33 C34 C35 175.20(18) . . . . ?
C33 C34 C35 C36 -0.6(4) . . . . ?
C34 C35 C36 C37 0.2(4) . . . . ?
C35 C36 C37 C38 0.1(4) . . . . ?
C36 C37 C38 C33 0.0(3) . . . . ?
C34 C33 C38 C37 -0.4(3) . . . . ?
Te2 C33 C38 C37 -174.96(17) . . . . ?
C44 C39 C40 C41 -1.0(3) . . . . ?
Se2 C39 C40 C41 -178.10(18) . . . . ?
C39 C40 C41 C42 1.5(4) . . . . ?
C40 C41 C42 C43 -0.6(4) . . . . ?
C41 C42 C43 C44 -0.8(4) . . . . ?
C42 C43 C44 C39 1.3(4) . . . . ?
C40 C39 C44 C43 -0.4(3) . . . . ?
Se2 C39 C44 C43 176.90(19) . . . . ?

_refine_diff_density_max         0.419
_refine_diff_density_min         -1.126
_refine_diff_density_rms         0.133

