# Electronic Supplementary Material (ESI) for RSC Advances.
# This journal is © The Royal Society of Chemistry 2014

#######################################################################
#
#                 Cambridge Crystallographic Data Centre
#                                CCDC 
# 
#######################################################################
# 
#  This CIF contains data from an original supplementary publication
#  deposited with the CCDC, and may include chemical, crystal,
#  experimental, refinement, atomic coordinates,
#  anisotropic displacement parameters and molecular geometry data,
#  as required by the journal to which it was submitted.
#
#  This CIF is provided on the understanding that it is used for bona
#  fide research purposes only. It may contain copyright material
#  of the CCDC or of third parties, and may not be copied or further
#  disseminated in any form, whether machine-readable or not,
#  except for the purpose of generating routine backup copies
#  on your local computer system.
# 
#  For further information on the CCDC, data deposition and
#  data retrieval see:
#                         www.ccdc.cam.ac.uk
#
#  Bona fide researchers may freely download Mercury and enCIFer
#  from this site to visualise CIF-encoded structures and 
#  to carry out CIF format checking respectively.
#
data_phcptph1

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          403K
_chemical_formula_moiety         'C23 H24 O2 S'
_chemical_formula_sum            'C23 H24 O2 S'
_chemical_formula_weight         364.49

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'

_symmetry_cell_setting           Monoclinic
_symmetry_space_group_name_H-M   C2/c
_symmetry_space_group_name_Hall  '-C 2yc'
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y, -z+1/2'
'x+1/2, y+1/2, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y, z-1/2'
'-x+1/2, -y+1/2, -z'
'x+1/2, -y+1/2, z-1/2'

_cell_length_a                   40.4991(18)
_cell_length_b                   5.92780(10)
_cell_length_c                   16.1917(6)
_cell_angle_alpha                90.00
_cell_angle_beta                 106.414(6)
_cell_angle_gamma                90.00
_cell_volume                     3728.7(2)
_cell_formula_units_Z            8
_cell_measurement_temperature    153(2)
_cell_measurement_reflns_used    3279
_cell_measurement_theta_min      2.62
_cell_measurement_theta_max      31.41

_exptl_crystal_description       needle
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.39
_exptl_crystal_size_mid          0.31
_exptl_crystal_size_min          0.20
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.299
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1552
_exptl_absorpt_coefficient_mu    0.188
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.463
_exptl_absorpt_correction_T_max  0.592
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.31 (release 14-01-2014 CrysAlis171 .NET)
(compiled Jan 14 2014,18:38:05)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      153(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  ?
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            15721
_diffrn_reflns_av_R_equivalents  0.0339
_diffrn_reflns_av_sigmaI/netI    0.0215
_diffrn_reflns_limit_h_min       -47
_diffrn_reflns_limit_h_max       48
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_theta_min         2.86
_diffrn_reflns_theta_max         25.00
_reflns_number_total             3273
_reflns_number_gt                3049
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_molecular_graphics    ?
_computing_publication_material  ?

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

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0328P)²+6.0268P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         3273
_refine_ls_number_parameters     237
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0381
_refine_ls_R_factor_gt           0.0356
_refine_ls_wR_factor_ref         0.0879
_refine_ls_wR_factor_gt          0.0860
_refine_ls_goodness_of_fit_ref   1.090
_refine_ls_restrained_S_all      1.090
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 0.15411(4) 0.3700(3) -0.07462(10) 0.0164(3) Uani 1 1 d . . .
H1 H 0.1711 0.3383 -0.0238 0.020 Uiso 1 1 calc R . .
C2 C 0.14793(4) 0.2186(3) -0.14217(11) 0.0185(3) Uani 1 1 d . . .
H2 H 0.1610 0.0876 -0.1370 0.022 Uiso 1 1 calc R . .
C3 C 0.12227(4) 0.2617(3) -0.21766(11) 0.0193(4) Uani 1 1 d . . .
H3 H 0.1179 0.1592 -0.2630 0.023 Uiso 1 1 calc R . .
C4 C 0.10312(4) 0.4591(3) -0.22518(10) 0.0181(3) Uani 1 1 d . . .
H4 H 0.0857 0.4876 -0.2755 0.022 Uiso 1 1 calc R . .
C5 C 0.10975(4) 0.6132(3) -0.15844(10) 0.0165(3) Uani 1 1 d . . .
H5 H 0.0972 0.7465 -0.1648 0.020 Uiso 1 1 calc R . .
C6 C 0.13520(4) 0.5709(3) -0.08142(10) 0.0147(3) Uani 1 1 d . . .
C7 C 0.14181(4) 0.7307(3) -0.00977(10) 0.0146(3) Uani 1 1 d . . .
C8 C 0.12243(4) 0.9052(3) 0.00743(10) 0.0142(3) Uani 1 1 d . . .
C9 C 0.13820(4) 1.0211(3) 0.08492(10) 0.0145(3) Uani 1 1 d . . .
C10 C 0.16972(4) 0.9379(3) 0.12960(10) 0.0153(3) Uani 1 1 d . . .
C11 C 0.19236(4) 0.9967(3) 0.21472(10) 0.0155(3) Uani 1 1 d . . .
C12 C 0.18913(4) 1.2042(3) 0.25320(11) 0.0187(4) Uani 1 1 d . . .
H12 H 0.1738 1.3118 0.2226 0.022 Uiso 1 1 calc R . .
C13 C 0.20868(4) 1.2503(3) 0.33665(11) 0.0216(4) Uani 1 1 d . . .
H13 H 0.2060 1.3874 0.3620 0.026 Uiso 1 1 calc R . .
C14 C 0.23213(4) 1.0935(3) 0.38246(11) 0.0227(4) Uani 1 1 d . . .
H14 H 0.2449 1.1240 0.4388 0.027 Uiso 1 1 calc R . .
C15 C 0.23647(4) 0.8910(3) 0.34409(11) 0.0217(4) Uani 1 1 d . . .
H15 H 0.2526 0.7872 0.3742 0.026 Uiso 1 1 calc R . .
C16 C 0.21683(4) 0.8428(3) 0.26126(10) 0.0189(4) Uani 1 1 d . . .
H16 H 0.2199 0.7063 0.2361 0.023 Uiso 1 1 calc R . .
C17 C 0.08746(4) 1.0028(3) -0.03549(10) 0.0154(3) Uani 1 1 d . . .
H17A H 0.0704 0.8845 -0.0538 0.019 Uiso 1 1 calc R . .
H17B H 0.0879 1.0934 -0.0850 0.019 Uiso 1 1 calc R . .
C18 C 0.11529(4) 1.2077(3) 0.09966(10) 0.0150(3) Uani 1 1 d . . .
H18A H 0.1234 1.3537 0.0868 0.018 Uiso 1 1 calc R . .
H18B H 0.1142 1.2077 0.1587 0.018 Uiso 1 1 calc R . .
C19 C 0.07960(4) 1.1511(3) 0.03605(10) 0.0148(3) Uani 1 1 d . . .
C20 C 0.06071(4) 1.3664(3) -0.00075(10) 0.0167(3) Uani 1 1 d . . .
H20A H 0.0567 1.4570 0.0453 0.020 Uiso 1 1 calc R . .
H20B H 0.0746 1.4538 -0.0291 0.020 Uiso 1 1 calc R . .
C21 C 0.01220(4) 1.5037(3) -0.10431(12) 0.0256(4) Uani 1 1 d . . .
H21A H 0.0092 1.6122 -0.0630 0.038 Uiso 1 1 calc R . .
H21B H -0.0099 1.4620 -0.1418 0.038 Uiso 1 1 calc R . .
H21C H 0.0260 1.5684 -0.1376 0.038 Uiso 1 1 calc R . .
C22 C 0.05830(4) 1.0128(3) 0.08206(10) 0.0158(3) Uani 1 1 d . . .
H22A H 0.0360 0.9789 0.0426 0.019 Uiso 1 1 calc R . .
H22B H 0.0699 0.8715 0.1022 0.019 Uiso 1 1 calc R . .
C23 C 0.03421(4) 1.0242(3) 0.19886(11) 0.0216(4) Uani 1 1 d . . .
H23A H 0.0121 0.9872 0.1603 0.032 Uiso 1 1 calc R . .
H23B H 0.0312 1.1192 0.2442 0.032 Uiso 1 1 calc R . .
H23C H 0.0458 0.8881 0.2232 0.032 Uiso 1 1 calc R . .
O1 O 0.02885(3) 1.30988(18) -0.06073(8) 0.0204(3) Uani 1 1 d . . .
O2 O 0.05416(3) 1.13925(19) 0.15301(7) 0.0189(3) Uani 1 1 d . . .
S1 S 0.180223(10) 0.71304(7) 0.07236(3) 0.01633(12) Uani 1 1 d . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C1 C2 1.382(2) . ?
C1 C6 1.403(2) . ?
C2 C3 1.386(2) . ?
C3 C4 1.390(2) . ?
C4 C5 1.383(2) . ?
C5 C6 1.398(2) . ?
C6 C7 1.463(2) . ?
C7 C8 1.373(2) . ?
C7 S1 1.7408(16) . ?
C8 C9 1.415(2) . ?
C8 C17 1.506(2) . ?
C9 C10 1.369(2) . ?
C9 C18 1.505(2) . ?
C10 C11 1.466(2) . ?
C10 S1 1.7433(16) . ?
C11 C16 1.400(2) . ?
C11 C12 1.402(2) . ?
C12 C13 1.387(2) . ?
C13 C14 1.385(3) . ?
C14 C15 1.385(2) . ?
C15 C16 1.382(2) . ?
C17 C19 1.557(2) . ?
C18 C19 1.556(2) . ?
C19 C20 1.520(2) . ?
C19 C22 1.528(2) . ?
C20 O1 1.4185(19) . ?
C21 O1 1.416(2) . ?
C22 O2 1.4205(18) . ?
C23 O2 1.4174(19) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C2 C1 C6 121.08(15) . . ?
C1 C2 C3 120.08(15) . . ?
C2 C3 C4 119.54(15) . . ?
C5 C4 C3 120.51(15) . . ?
C4 C5 C6 120.66(15) . . ?
C5 C6 C1 118.10(14) . . ?
C5 C6 C7 120.98(14) . . ?
C1 C6 C7 120.92(14) . . ?
C8 C7 C6 131.42(14) . . ?
C8 C7 S1 109.21(12) . . ?
C6 C7 S1 119.37(11) . . ?
C7 C8 C9 113.90(14) . . ?
C7 C8 C17 135.45(14) . . ?
C9 C8 C17 110.64(13) . . ?
C10 C9 C8 114.40(14) . . ?
C10 C9 C18 134.87(15) . . ?
C8 C9 C18 110.71(13) . . ?
C9 C10 C11 130.79(15) . . ?
C9 C10 S1 109.01(12) . . ?
C11 C10 S1 120.00(12) . . ?
C16 C11 C12 118.26(15) . . ?
C16 C11 C10 120.72(14) . . ?
C12 C11 C10 120.97(14) . . ?
C13 C12 C11 120.44(16) . . ?
C14 C13 C12 120.40(16) . . ?
C13 C14 C15 119.74(16) . . ?
C16 C15 C14 120.22(16) . . ?
C15 C16 C11 120.87(16) . . ?
C8 C17 C19 103.71(12) . . ?
C9 C18 C19 103.62(12) . . ?
C20 C19 C22 110.51(13) . . ?
C20 C19 C18 110.41(12) . . ?
C22 C19 C18 109.86(13) . . ?
C20 C19 C17 111.62(13) . . ?
C22 C19 C17 108.81(12) . . ?
C18 C19 C17 105.50(12) . . ?
O1 C20 C19 109.26(12) . . ?
O2 C22 C19 108.86(12) . . ?
C21 O1 C20 111.27(12) . . ?
C23 O2 C22 112.62(12) . . ?
C7 S1 C10 93.46(7) . . ?

_diffrn_measured_fraction_theta_max 0.998
_diffrn_reflns_theta_full        25.00
_diffrn_measured_fraction_theta_full 0.998
_refine_diff_density_max         0.286
_refine_diff_density_min         -0.248
_refine_diff_density_rms         0.046
_database_code_depnum_ccdc_archive 'CCDC 995427'
#######################################################################
#
#                 Cambridge Crystallographic Data Centre
#                                CCDC 
# 
#######################################################################
# 
#  This CIF contains data from an original supplementary publication
#  deposited with the CCDC, and may include chemical, crystal,
#  experimental, refinement, atomic coordinates,
#  anisotropic displacement parameters and molecular geometry data,
#  as required by the journal to which it was submitted.
#
#  This CIF is provided on the understanding that it is used for bona
#  fide research purposes only. It may contain copyright material
#  of the CCDC or of third parties, and may not be copied or further
#  disseminated in any form, whether machine-readable or not,
#  except for the purpose of generating routine backup copies
#  on your local computer system.
# 
#  For further information on the CCDC, data deposition and
#  data retrieval see:
#                         www.ccdc.cam.ac.uk
#
#  Bona fide researchers may freely download Mercury and enCIFer
#  from this site to visualise CIF-encoded structures and 
#  to carry out CIF format checking respectively.
#
data_benzyl_1

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          '423 K'
_chemical_formula_moiety         'C23 H24 O2 Se'
_chemical_formula_sum            'C23 H24 O2 Se'
_chemical_formula_weight         411.38

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'

_symmetry_cell_setting           Monoclinic
_symmetry_space_group_name_H-M   C2/c
_symmetry_space_group_name_Hall  '-C 2yc'

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

_cell_length_a                   34.8342(19)
_cell_length_b                   5.7765(3)
_cell_length_c                   22.9523(12)
_cell_angle_alpha                90.00
_cell_angle_beta                 123.6070(10)
_cell_angle_gamma                90.00
_cell_volume                     3846.5(4)
_cell_formula_units_Z            8
_cell_measurement_temperature    273(2)
_cell_measurement_reflns_used    8348
_cell_measurement_theta_min      2.81
_cell_measurement_theta_max      33.71

_exptl_crystal_description       needle
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.40
_exptl_crystal_size_mid          0.31
_exptl_crystal_size_min          0.21
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.421
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1696
_exptl_absorpt_coefficient_mu    1.966
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.486
_exptl_absorpt_correction_T_max  0.662
_exptl_absorpt_process_details   'SADABS; BRUKER, 2008'
_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      273(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            20054
_diffrn_reflns_av_R_equivalents  0.0360
_diffrn_reflns_av_sigmaI/netI    0.0285
_diffrn_reflns_limit_h_min       -44
_diffrn_reflns_limit_h_max       44
_diffrn_reflns_limit_k_min       -6
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_l_min       -27
_diffrn_reflns_limit_l_max       29
_diffrn_reflns_theta_min         1.79
_diffrn_reflns_theta_max         27.00
_reflns_number_total             4203
_reflns_number_gt                3682
_reflns_threshold_expression     >2sigma(I)

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

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

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0188P)²+4.7352P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         4203
_refine_ls_number_parameters     237
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0307
_refine_ls_R_factor_gt           0.0239
_refine_ls_wR_factor_ref         0.0572
_refine_ls_wR_factor_gt          0.0547
_refine_ls_goodness_of_fit_ref   1.079
_refine_ls_restrained_S_all      1.079
_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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 0.11261(5) 0.4687(3) 0.46926(8) 0.0155(3) Uani 1 1 d . . .
C2 C 0.10035(6) 0.3253(3) 0.50550(10) 0.0243(4) Uani 1 1 d . . .
H2 H 0.0844 0.1887 0.4848 0.029 Uiso 1 1 calc R . .
C3 C 0.11154(7) 0.3829(4) 0.57160(11) 0.0326(5) Uani 1 1 d . . .
H3 H 0.1033 0.2844 0.5950 0.039 Uiso 1 1 calc R . .
C4 C 0.13475(8) 0.5855(4) 0.60297(11) 0.0341(5) Uani 1 1 d . . .
H4 H 0.1427 0.6227 0.6478 0.041 Uiso 1 1 calc R . .
C5 C 0.14608(8) 0.7329(4) 0.56733(11) 0.0336(5) Uani 1 1 d . . .
H5 H 0.1614 0.8708 0.5881 0.040 Uiso 1 1 calc R . .
C6 C 0.13468(7) 0.6765(3) 0.50085(10) 0.0239(4) Uani 1 1 d . . .
H6 H 0.1419 0.7790 0.4770 0.029 Uiso 1 1 calc R . .
C7 C 0.10436(5) 0.4005(3) 0.40189(8) 0.0138(3) Uani 1 1 d . . .
C8 C 0.12396(5) 0.4775(3) 0.36771(8) 0.0129(3) Uani 1 1 d . . .
C9 C 0.16049(5) 0.6556(3) 0.38413(8) 0.0130(3) Uani 1 1 d . . .
H9A H 0.1855 0.6506 0.4332 0.016 Uiso 1 1 calc R . .
H9B H 0.1476 0.8105 0.3726 0.016 Uiso 1 1 calc R . .
C10 C 0.17724(5) 0.5815(3) 0.33665(8) 0.0123(3) Uani 1 1 d . . .
C11 C 0.21492(5) 0.3983(3) 0.37357(8) 0.0135(3) Uani 1 1 d . . .
H11A H 0.2029 0.2641 0.3839 0.016 Uiso 1 1 calc R . .
H11B H 0.2245 0.3495 0.3431 0.016 Uiso 1 1 calc R . .
C12 C 0.28865(6) 0.3195(3) 0.47035(10) 0.0227(4) Uani 1 1 d . . .
H12A H 0.2765 0.1820 0.4780 0.034 Uiso 1 1 calc R . .
H12B H 0.3135 0.3788 0.5145 0.034 Uiso 1 1 calc R . .
H12C H 0.2998 0.2834 0.4414 0.034 Uiso 1 1 calc R . .
C13 C 0.19370(6) 0.7867(3) 0.31503(9) 0.0151(3) Uani 1 1 d . . .
H13A H 0.1705 0.9075 0.2957 0.018 Uiso 1 1 calc R . .
H13B H 0.2218 0.8489 0.3554 0.018 Uiso 1 1 calc R . .
C14 C 0.21917(7) 0.8952(3) 0.24358(12) 0.0293(4) Uani 1 1 d . . .
H14A H 0.1985 1.0247 0.2283 0.044 Uiso 1 1 calc R . .
H14B H 0.2216 0.8443 0.2059 0.044 Uiso 1 1 calc R . .
H14C H 0.2490 0.9409 0.2826 0.044 Uiso 1 1 calc R . .
C15 C 0.13489(5) 0.4613(3) 0.27304(8) 0.0128(3) Uani 1 1 d . . .
H15A H 0.1160 0.5716 0.2361 0.015 Uiso 1 1 calc R . .
H15B H 0.1444 0.3392 0.2546 0.015 Uiso 1 1 calc R . .
C16 C 0.10948(5) 0.3640(3) 0.30341(8) 0.0127(3) Uani 1 1 d . . .
C17 C 0.07840(5) 0.1893(3) 0.28347(8) 0.0136(3) Uani 1 1 d . . .
C18 C 0.05666(5) 0.0413(3) 0.22116(8) 0.0147(3) Uani 1 1 d . . .
C19 C 0.05277(6) 0.1153(3) 0.16018(9) 0.0191(4) Uani 1 1 d . . .
H19 H 0.0653 0.2569 0.1598 0.023 Uiso 1 1 calc R . .
C20 C 0.03043(6) -0.0197(3) 0.10033(10) 0.0266(4) Uani 1 1 d . . .
H20 H 0.0285 0.0311 0.0603 0.032 Uiso 1 1 calc R . .
C21 C 0.01096(6) -0.2301(3) 0.09959(10) 0.0281(4) Uani 1 1 d . . .
H21 H -0.0046 -0.3189 0.0590 0.034 Uiso 1 1 calc R . .
C22 C 0.01494(6) -0.3062(3) 0.15963(10) 0.0226(4) Uani 1 1 d . . .
H22 H 0.0021 -0.4475 0.1595 0.027 Uiso 1 1 calc R . .
C23 C 0.03784(5) -0.1743(3) 0.22011(9) 0.0176(3) Uani 1 1 d . . .
H23 H 0.0408 -0.2293 0.2605 0.021 Uiso 1 1 calc R . .
O1 O 0.25330(4) 0.4886(2) 0.43659(6) 0.0183(3) Uani 1 1 d . . .
O2 O 0.20207(4) 0.7125(2) 0.26403(7) 0.0200(3) Uani 1 1 d . . .
Se1 Se 0.063139(5) 0.15652(3) 0.350207(9) 0.01544(6) Uani 1 1 d . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C1 C6 1.393(2) . ?
C1 C2 1.398(2) . ?
C1 C7 1.462(2) . ?
C2 C3 1.382(3) . ?
C3 C4 1.377(3) . ?
C4 C5 1.381(3) . ?
C5 C6 1.386(3) . ?
C7 C8 1.368(2) . ?
C7 Se1 1.8892(16) . ?
C8 C16 1.428(2) . ?
C8 C9 1.513(2) . ?
C9 C10 1.554(2) . ?
C10 C13 1.515(2) . ?
C10 C11 1.526(2) . ?
C10 C15 1.551(2) . ?
C11 O1 1.4182(18) . ?
C12 O1 1.4192(19) . ?
C13 O2 1.420(2) . ?
C14 O2 1.414(2) . ?
C15 C16 1.506(2) . ?
C16 C17 1.361(2) . ?
C17 C18 1.466(2) . ?
C17 Se1 1.8886(17) . ?
C18 C19 1.396(2) . ?
C18 C23 1.401(2) . ?
C19 C20 1.385(2) . ?
C20 C21 1.388(3) . ?
C21 C22 1.378(3) . ?
C22 C23 1.385(2) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C6 C1 C2 117.62(16) . . ?
C6 C1 C7 120.77(16) . . ?
C2 C1 C7 121.57(16) . . ?
C3 C2 C1 121.13(18) . . ?
C4 C3 C2 120.37(19) . . ?
C3 C4 C5 119.47(19) . . ?
C4 C5 C6 120.36(19) . . ?
C5 C6 C1 120.97(18) . . ?
C8 C7 C1 130.56(15) . . ?
C8 C7 Se1 109.25(12) . . ?
C1 C7 Se1 120.10(12) . . ?
C7 C8 C16 116.12(14) . . ?
C7 C8 C9 134.12(15) . . ?
C16 C8 C9 109.69(13) . . ?
C8 C9 C10 103.22(12) . . ?
C13 C10 C11 111.06(12) . . ?
C13 C10 C15 112.17(13) . . ?
C11 C10 C15 106.85(13) . . ?
C13 C10 C9 111.79(13) . . ?
C11 C10 C9 110.05(13) . . ?
C15 C10 C9 104.63(12) . . ?
O1 C11 C10 110.30(13) . . ?
O2 C13 C10 108.74(13) . . ?
C16 C15 C10 103.17(12) . . ?
C17 C16 C8 116.65(15) . . ?
C17 C16 C15 133.07(15) . . ?
C8 C16 C15 110.20(13) . . ?
C16 C17 C18 130.22(15) . . ?
C16 C17 Se1 109.28(12) . . ?
C18 C17 Se1 120.49(12) . . ?
C19 C18 C23 118.03(15) . . ?
C19 C18 C17 120.68(15) . . ?
C23 C18 C17 121.25(16) . . ?
C20 C19 C18 120.75(17) . . ?
C19 C20 C21 120.54(18) . . ?
C22 C21 C20 119.28(17) . . ?
C21 C22 C23 120.66(17) . . ?
C22 C23 C18 120.71(17) . . ?
C11 O1 C12 110.30(13) . . ?
C14 O2 C13 111.38(13) . . ?
C17 Se1 C7 88.70(7) . . ?

_diffrn_measured_fraction_theta_max 1.000
_diffrn_reflns_theta_full        27.00
_diffrn_measured_fraction_theta_full 1.000
_refine_diff_density_max         0.424
_refine_diff_density_min         -0.235
_refine_diff_density_rms         0.057
_database_code_depnum_ccdc_archive 'CCDC 998094'
