# Electronic Supplementary Material (ESI) for RSC Advances.
# This journal is © The Royal Society of Chemistry 2016

####################################################################### 
# 
# 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_2007slh0123_Se4
_database_code_depnum_ccdc_archive 'CCDC 1489811'
_audit_update_record             
;
2016-07-04 deposited with the CCDC.
2016-09-21 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
"bis[8-(methylselanyl)naphthyl] 1,1'-diselenide"
_chemical_name_common            ?
_chemical_melting_point          '405.7--406.4 K'
_chemical_formula_moiety         ?
_chemical_formula_sum            'C22 H18 Se4'
_chemical_formula_weight         598.20

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

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                   24.6455(8)
_cell_length_b                   10.5901(4)
_cell_length_c                   7.9658(2)
_cell_angle_alpha                90.00
_cell_angle_beta                 106.662(2)
_cell_angle_gamma                90.00
_cell_volume                     1991.77(11)
_cell_formula_units_Z            4
_cell_measurement_temperature    120(2)
_cell_measurement_reflns_used    8215
_cell_measurement_theta_min      2.91
_cell_measurement_theta_max      27.48

_exptl_crystal_description       prisms
_exptl_crystal_colour            'light yellow'
_exptl_crystal_size_max          0.20
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.20
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.995
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1144
_exptl_absorpt_coefficient_mu    7.371
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.3203
_exptl_absorpt_correction_T_max  0.3203
#Note that T_min and T_max were calculated based on 
#the reported crystal dimension. The experimental 
#ratio of minimum and maximum transmission is 0.768183
_exptl_absorpt_process_details   'SADABS V2.10 (Sheldrick, G.M., 2003)'

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      120(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_source         'Bruker-Nonius FR591 rotating anode'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Bruker-Nonius 95mm CCD camera on'
_diffrn_measurement_method       '_f & _w scans'
_diffrn_detector_area_resol_mean 9.091
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            11312
_diffrn_reflns_av_R_equivalents  0.0339
_diffrn_reflns_av_sigmaI/netI    0.0294
_diffrn_reflns_limit_h_min       -32
_diffrn_reflns_limit_h_max       31
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_limit_l_max       9
_diffrn_reflns_theta_min         3.20
_diffrn_reflns_theta_max         27.50
_reflns_number_total             2291
_reflns_number_gt                2124
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'COLLECT (Hooft, R.W.W., 1998)'
_computing_cell_refinement       
'DENZO (Otwinowski & Minor, 1997) & COLLECT (Hooft, R.W.W., 1998)'
#Although determined using DirAx, the cell is refined in the HKL
#package during data reduction
_computing_data_reduction        
'DENZO (Otwinowski & Minor, 1997) & COLLECT (Hooft, R.W.W., 1998)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1997)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_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/[_s²(Fo²)+(0.0083P)²+3.2063P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     SHELXL
_refine_ls_extinction_coef       0.00116(9)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²_l³/sin(2_q)]^-1/4^
_refine_ls_number_reflns         2291
_refine_ls_number_parameters     120
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0238
_refine_ls_R_factor_gt           0.0201
_refine_ls_wR_factor_ref         0.0437
_refine_ls_wR_factor_gt          0.0423
_refine_ls_goodness_of_fit_ref   1.080
_refine_ls_restrained_S_all      1.080
_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 0.08548(8) 0.26083(19) 0.7996(3) 0.0128(4) Uani 1 1 d . . .
C2 C 0.06424(8) 0.3403(2) 0.9017(3) 0.0151(4) Uani 1 1 d . . .
H2 H 0.0267 0.3275 0.9075 0.018 Uiso 1 1 calc R . .
C3 C 0.09634(9) 0.4400(2) 0.9980(3) 0.0188(5) Uani 1 1 d . . .
H3 H 0.0801 0.4948 1.0649 0.023 Uiso 1 1 calc R . .
C4 C 0.15088(9) 0.4573(2) 0.9949(3) 0.0165(4) Uani 1 1 d . . .
H4 H 0.1729 0.5233 1.0621 0.020 Uiso 1 1 calc R . .
C5 C 0.17487(9) 0.37822(19) 0.8927(2) 0.0133(4) Uani 1 1 d . . .
C6 C 0.23232(9) 0.3971(2) 0.8971(3) 0.0156(4) Uani 1 1 d . . .
H6 H 0.2536 0.4620 0.9690 0.019 Uiso 1 1 calc R . .
C7 C 0.25745(8) 0.3241(2) 0.8000(3) 0.0178(4) Uani 1 1 d . . .
H7 H 0.2963 0.3358 0.8072 0.021 Uiso 1 1 calc R . .
C8 C 0.22531(8) 0.2311(2) 0.6891(3) 0.0159(4) Uani 1 1 d . . .
H8 H 0.2426 0.1818 0.6188 0.019 Uiso 1 1 calc R . .
C9 C 0.16948(8) 0.20962(19) 0.6798(3) 0.0134(4) Uani 1 1 d . . .
C10 C 0.14213(8) 0.27959(19) 0.7869(2) 0.0114(4) Uani 1 1 d . . .
C11 C 0.09340(10) 0.2091(2) 0.3246(3) 0.0266(5) Uani 1 1 d . . .
H11A H 0.0647 0.2563 0.3620 0.040 Uiso 1 1 calc R . .
H11B H 0.0753 0.1640 0.2155 0.040 Uiso 1 1 calc R . .
H11C H 0.1217 0.2679 0.3051 0.040 Uiso 1 1 calc R . .
Se1 Se 0.130348(8) 0.08778(2) 0.50642(3) 0.01443(8) Uani 1 1 d . . .
Se2 Se 0.037070(8) 0.121370(19) 0.68108(2) 0.01261(8) Uani 1 1 d . . .

loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
C1 0.0132(9) 0.0102(10) 0.0125(10) 0.0012(8) -0.0001(7) -0.0004(7)
C2 0.0159(10) 0.0147(11) 0.0153(10) -0.0007(8) 0.0057(8) -0.0009(8)
C3 0.0231(11) 0.0177(11) 0.0170(11) -0.0037(9) 0.0081(8) -0.0010(9)
C4 0.0211(11) 0.0132(10) 0.0130(10) -0.0012(8) 0.0014(8) -0.0039(8)
C5 0.0165(10) 0.0116(10) 0.0104(10) 0.0040(8) 0.0014(8) -0.0011(8)
C6 0.0169(10) 0.0150(11) 0.0129(10) 0.0039(8) 0.0010(8) -0.0041(8)
C7 0.0132(9) 0.0176(11) 0.0213(11) 0.0079(9) 0.0028(8) -0.0022(8)
C8 0.0163(10) 0.0152(11) 0.0168(10) 0.0053(8) 0.0054(8) 0.0037(8)
C9 0.0135(9) 0.0124(10) 0.0134(10) 0.0039(8) 0.0022(7) 0.0013(8)
C10 0.0121(9) 0.0105(10) 0.0103(9) 0.0023(8) 0.0010(7) 0.0006(7)
C11 0.0337(13) 0.0232(13) 0.0174(11) 0.0030(10) -0.0015(9) 0.0014(10)
Se1 0.01522(12) 0.01289(13) 0.01566(12) -0.00190(8) 0.00521(8) 0.00143(8)
Se2 0.01102(11) 0.01086(12) 0.01547(12) -0.00177(8) 0.00305(8) -0.00038(7)

_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 1.374(3) . ?
C1 C10 1.442(3) . ?
C1 Se2 1.962(2) . ?
C2 C3 1.407(3) . ?
C2 H2 0.9500 . ?
C3 C4 1.364(3) . ?
C3 H3 0.9500 . ?
C4 C5 1.411(3) . ?
C4 H4 0.9500 . ?
C5 C6 1.421(3) . ?
C5 C10 1.436(3) . ?
C6 C7 1.362(3) . ?
C6 H6 0.9500 . ?
C7 C8 1.406(3) . ?
C7 H7 0.9500 . ?
C8 C9 1.375(3) . ?
C8 H8 0.9500 . ?
C9 C10 1.436(3) . ?
C9 Se1 1.933(2) . ?
C11 Se1 1.955(2) . ?
C11 H11A 0.9800 . ?
C11 H11B 0.9800 . ?
C11 H11C 0.9800 . ?
Se2 Se2 2.3864(4) 2_556 ?

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 C10 119.86(18) . . ?
C2 C1 Se2 117.61(15) . . ?
C10 C1 Se2 122.51(15) . . ?
C1 C2 C3 122.14(19) . . ?
C1 C2 H2 118.9 . . ?
C3 C2 H2 118.9 . . ?
C4 C3 C2 119.6(2) . . ?
C4 C3 H3 120.2 . . ?
C2 C3 H3 120.2 . . ?
C3 C4 C5 120.57(19) . . ?
C3 C4 H4 119.7 . . ?
C5 C4 H4 119.7 . . ?
C4 C5 C6 118.80(19) . . ?
C4 C5 C10 120.85(19) . . ?
C6 C5 C10 120.35(19) . . ?
C7 C6 C5 121.22(19) . . ?
C7 C6 H6 119.4 . . ?
C5 C6 H6 119.4 . . ?
C6 C7 C8 119.26(19) . . ?
C6 C7 H7 120.4 . . ?
C8 C7 H7 120.4 . . ?
C9 C8 C7 121.6(2) . . ?
C9 C8 H8 119.2 . . ?
C7 C8 H8 119.2 . . ?
C8 C9 C10 121.03(18) . . ?
C8 C9 Se1 115.79(15) . . ?
C10 C9 Se1 123.09(14) . . ?
C9 C10 C5 116.34(17) . . ?
C9 C10 C1 126.82(18) . . ?
C5 C10 C1 116.84(18) . . ?
Se1 C11 H11A 109.5 . . ?
Se1 C11 H11B 109.5 . . ?
H11A C11 H11B 109.5 . . ?
Se1 C11 H11C 109.5 . . ?
H11A C11 H11C 109.5 . . ?
H11B C11 H11C 109.5 . . ?
C9 Se1 C11 96.98(9) . . ?
C1 Se2 Se2 102.64(6) . 2_556 ?

_diffrn_measured_fraction_theta_max 0.998
_diffrn_reflns_theta_full        27.50
_diffrn_measured_fraction_theta_full 0.998
_refine_diff_density_max         0.379
_refine_diff_density_min         -0.419
_refine_diff_density_rms         0.083


_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: hexane'
