# Electronic Supplementary Material (ESI) for Organic & Biomolecular Chemistry.
# 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_test5
_database_code_depnum_ccdc_archive 'CCDC 1495950'
_audit_update_record             
;
2016-07-25 deposited with the CCDC.
2016-10-12 downloaded from the CCDC.
;

_audit_creation_date             2016-07-22T11:10:19-00:00
_audit_creation_method           'WinGX routine CIF_UPDATE'
_audit_conform_dict_name         cif_core.dic
_audit_conform_dict_version      2.4
_audit_conform_dict_location     ftp://ftp.iucr.org/pub/cif_core.dic

#----------------------------------------------------------------------------#
#                   CHEMICAL INFORMATION                                     #
#----------------------------------------------------------------------------#

_chemical_name_systematic        
'butyl(10- iodo-7- methylphenanthren-9- yl) selane'
_chemical_name_common            'butyl iodo methylphenanthren yl selane'
_chemical_formula_moiety         'C19 H19 I Se'
_chemical_formula_sum            'C19 H19 I Se'
_chemical_formula_weight         453.2
_chemical_melting_point          none
_chemical_absolute_configuration rmad
_space_group_crystal_system      triclinic
_space_group_name_H-M_alt        'P 1'
_space_group_name_Hall           'P 1'

#----------------------------------------------------------------------------#
#                   UNIT CELL INFORMATION                                    #
#----------------------------------------------------------------------------#

loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'

_cell_length_a                   8.4221(3)
_cell_length_b                   9.7770(3)
_cell_length_c                   11.8865(4)
_cell_angle_alpha                101.4230(10)
_cell_angle_beta                 98.2310(10)
_cell_angle_gamma                110.9600(10)
_cell_volume                     871.07(5)
_cell_formula_units_Z            2
_cell_measurement_temperature    290(2)
_cell_measurement_reflns_used    8563
_cell_measurement_theta_min      2.663
_cell_measurement_theta_max      25.143

#----------------------------------------------------------------------------#
#                   CRYSTAL INFORMATION                                      #
#----------------------------------------------------------------------------#

_exptl_crystal_description       tabular
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.416
_exptl_crystal_size_mid          0.363
_exptl_crystal_size_min          0.141
_exptl_crystal_density_meas      none
_exptl_crystal_density_diffrn    1.728
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             440
_exptl_special_details           
;
 ?
;

#----------------------------------------------------------------------------#
#                   ABSORPTION CORRECTION                                    #
#----------------------------------------------------------------------------#

_exptl_absorpt_coefficient_mu    3.919
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS (version 2012/1; Bruker, 2012) was used to perform the numerical
        absorption correction based on the indexed faces of the crystal.
;
_exptl_absorpt_correction_T_min  0.2402
_exptl_absorpt_correction_T_max  0.6656

#----------------------------------------------------------------------------#
#                   DATA COLLECTION                                          #
#----------------------------------------------------------------------------#

_diffrn_source                   'micro-focus tube'
_diffrn_ambient_temperature      290(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_monochromator  graphite
_diffrn_detector_area_resol_mean 10.4167
_diffrn_measurement_device_type  'Bruker D8 Quest Photon 100 diffractometer'
_diffrn_measurement_method       '2° φ & ω scans'
_diffrn_standards_number         none
_diffrn_standards_interval_count none
_diffrn_standards_interval_time  none
_diffrn_standards_decay_%        none
_diffrn_reflns_av_R_equivalents  0.0223
_diffrn_reflns_av_unetI/netI     0.0279
_diffrn_reflns_number            21065
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_theta_min         1.8
_diffrn_reflns_theta_max         27.51
_diffrn_reflns_theta_full        27.51
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.996
_reflns_number_total             6394
_reflns_number_gt                4982
_reflns_threshold_expression     >2σ(I)

#----------------------------------------------------------------------------#
#                   COMPUTER PROGRAMS USED                                   #
#----------------------------------------------------------------------------#

_computing_data_collection       'Bruker Instrument Service v4.2.7'
_computing_cell_refinement       'SAINT V8.34A (Bruker AXS Inc., 2013)'
_computing_data_reduction        'SAINT V8.34A (Bruker AXS Inc., 2013)'
_computing_structure_solution    'SHELXL-2008 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_molecular_graphics    'Diamond (version 3.2i; Crystal Impact GbR, Bo'

#----------------------------------------------------------------------------#
#                   STRUCTURE SOLUTION
#----------------------------------------------------------------------------#

_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom

#----------------------------------------------------------------------------#
#                   REFINEMENT INFORMATION                                   #
#----------------------------------------------------------------------------#

_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 > 2σ(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)+(0.0455P)²+0.3404P] where P=(Fo²+2Fc²)/3'
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       none
_refine_ls_number_reflns         6394
_refine_ls_number_parameters     379
_refine_ls_number_restraints     3
_refine_ls_R_factor_all          0.052
_refine_ls_R_factor_gt           0.036
_refine_ls_wR_factor_ref         0.0919
_refine_ls_wR_factor_gt          0.0847
_refine_ls_goodness_of_fit_ref   1.025
_refine_ls_restrained_S_all      1.025
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.00(2)
_refine_diff_density_max         0.496
_refine_diff_density_min         -0.374
_refine_diff_density_rms         0.063

#----------------------------------------------------------------------------#
#                   ATOMIC TYPES, COORDINATES AND THERMAL PARAMETERS         #
#----------------------------------------------------------------------------#

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 0 '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'
I I -0.4742 1.8119 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

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
C7 C 0.5265(7) 0.2740(6) 0.2161(5) 0.0591(14) Uani 1 1 d . . .
C12 C 0.6362(7) 0.1953(6) 0.2138(5) 0.0587(14) Uani 1 1 d . . .
C37 C 0.1851(6) 0.4622(6) 0.7997(5) 0.0554(12) Uani 1 1 d . . .
C31 C 0.0661(7) 0.5092(7) 0.6165(5) 0.0573(14) Uani 1 1 d . . .
C11 C 0.7484(8) 0.2128(7) 0.1377(5) 0.0673(15) Uani 1 1 d . . .
H11 H 0.8215 0.1606 0.1364 0.081 Uiso 1 1 calc R . .
C26 C 0.1737(7) 0.6656(7) 0.6597(5) 0.0544(13) Uani 1 1 d . . .
C24 C 0.3010(6) 0.6215(6) 0.8420(4) 0.0523(12) Uani 1 1 d . . .
C19 C 0.5879(12) -0.2174(10) 0.5075(8) 0.095(2) Uani 1 1 d . . .
H19A H 0.6707 -0.2627 0.497 0.142 Uiso 1 1 calc R . .
H19B H 0.4716 -0.2952 0.4826 0.142 Uiso 1 1 calc R . .
H19C H 0.6102 -0.1657 0.5893 0.142 Uiso 1 1 calc R . .
C27 C 0.1603(8) 0.7629(7) 0.5903(6) 0.0699(15) Uani 1 1 d . . .
H27 H 0.2296 0.8664 0.6188 0.084 Uiso 1 1 calc R . .
C8 C 0.5383(9) 0.3702(8) 0.1395(7) 0.0779(18) Uani 1 1 d . . .
H8 H 0.4676 0.4247 0.1398 0.093 Uiso 1 1 calc R . .
C25 C 0.2960(6) 0.7168(6) 0.7738(5) 0.0536(12) Uani 1 1 d . . .
C13 C 0.6300(7) 0.0963(6) 0.2928(5) 0.0541(13) Uani 1 1 d . . .
C30 C -0.0509(8) 0.4615(8) 0.5032(6) 0.0728(17) Uani 1 1 d . . .
H30 H -0.1272 0.3598 0.4737 0.087 Uiso 1 1 calc R . .
C35 C 0.0746(11) 0.2091(9) 0.8302(8) 0.079(2) Uani 1 1 d . . .
C18 C 0.5108(6) 0.0795(6) 0.3663(4) 0.0554(13) Uani 1 1 d . . .
C5 C 0.4028(6) 0.1656(6) 0.3677(4) 0.0534(12) Uani 1 1 d . . .
C32 C 0.0677(7) 0.4055(7) 0.6874(5) 0.0612(15) Uani 1 1 d . . .
C16 C 0.6056(9) -0.1062(7) 0.4354(6) 0.0628(16) Uani 1 1 d . . .
C22 C 0.1992(18) 0.770(2) 1.0786(9) 0.204(9) Uani 1 1 d . . .
H22A H 0.1276 0.7244 0.9987 0.244 Uiso 1 1 calc R . .
H22B H 0.2652 0.8767 1.0853 0.244 Uiso 1 1 calc R . .
C6 C 0.4078(6) 0.2548(6) 0.2946(5) 0.0582(13) Uani 1 1 d . . .
C21 C 0.0789(14) 0.7619(17) 1.1608(9) 0.150(5) Uani 1 1 d . . .
H21A H 0.0015 0.6572 1.1513 0.18 Uiso 1 1 calc R . .
H21B H 0.145 0.8058 1.2422 0.18 Uiso 1 1 calc R . .
C17 C 0.5005(8) -0.0248(6) 0.4345(5) 0.0632(14) Uani 1 1 d . . .
H17 H 0.4193 -0.0396 0.4811 0.076 Uiso 1 1 calc R . .
C15 C 0.7230(9) -0.0828(8) 0.3638(6) 0.0785(18) Uani 1 1 d . . .
H15 H 0.7961 -0.1351 0.3627 0.094 Uiso 1 1 calc R . .
C14 C 0.7344(8) 0.0131(8) 0.2960(6) 0.0719(16) Uani 1 1 d . . .
H14 H 0.8152 0.0248 0.2491 0.086 Uiso 1 1 calc R . .
C36 C 0.1837(9) 0.3573(7) 0.8681(6) 0.0679(15) Uani 1 1 d . . .
H36 H 0.2612 0.3925 0.9416 0.082 Uiso 1 1 calc R . .
C3 C 0.5268(10) 0.4151(8) 0.6363(6) 0.0695(16) Uani 1 1 d . . .
H3A H 0.4495 0.4683 0.6317 0.083 Uiso 1 1 calc R . .
H3B H 0.585 0.4243 0.5717 0.083 Uiso 1 1 calc R . .
C28 C 0.0485(8) 0.7098(9) 0.4826(6) 0.0808(18) Uani 1 1 d . . .
H28 H 0.0419 0.7771 0.4386 0.097 Uiso 1 1 calc R . .
C33 C -0.0420(8) 0.2510(7) 0.6499(6) 0.0766(17) Uani 1 1 d . . .
H33 H -0.1169 0.212 0.5752 0.092 Uiso 1 1 calc R . .
C4 C 0.4211(11) 0.2515(9) 0.6225(7) 0.083(2) Uani 1 1 d . . .
H4A H 0.3618 0.2435 0.6866 0.1 Uiso 1 1 calc R . .
H4B H 0.4998 0.2 0.6301 0.1 Uiso 1 1 calc R . .
C9 C 0.6474(11) 0.3851(9) 0.0671(7) 0.090(2) Uani 1 1 d . . .
H9 H 0.6519 0.4493 0.0184 0.108 Uiso 1 1 calc R . .
C29 C -0.0546(9) 0.5578(10) 0.4379(6) 0.086(2) Uani 1 1 d . . .
H29 H -0.1271 0.5217 0.3624 0.103 Uiso 1 1 calc R . .
C10 C 0.7533(10) 0.3054(9) 0.0646(6) 0.086(2) Uani 1 1 d . . .
H10 H 0.8279 0.3145 0.0134 0.103 Uiso 1 1 calc R . .
C2 C 0.6643(11) 0.4904(10) 0.7537(6) 0.090(2) Uani 1 1 d . . .
H2A H 0.6064 0.48 0.8184 0.108 Uiso 1 1 calc R . .
H2B H 0.743 0.4385 0.7579 0.108 Uiso 1 1 calc R . .
C23 C 0.3113(13) 0.7061(17) 1.0921(6) 0.150(5) Uani 1 1 d . . .
H23A H 0.2432 0.6023 1.0919 0.18 Uiso 1 1 calc R . .
H23B H 0.3842 0.7565 1.1714 0.18 Uiso 1 1 calc R . .
C34 C -0.0423(9) 0.1559(8) 0.7194(7) 0.090(2) Uani 1 1 d . . .
H34 H -0.1208 0.0547 0.6931 0.108 Uiso 1 1 calc R . .
C1 C 0.7690(11) 0.6572(9) 0.7676(7) 0.094(2) Uani 1 1 d . . .
H1A H 0.8531 0.7003 0.842 0.142 Uiso 1 1 calc R . .
H1B H 0.6917 0.7094 0.7649 0.142 Uiso 1 1 calc R . .
H1C H 0.8285 0.6679 0.7047 0.142 Uiso 1 1 calc R . .
C38 C 0.0669(15) 0.1015(10) 0.9050(9) 0.114(3) Uani 1 1 d . . .
H38A H -0.0188 0.002 0.8624 0.171 Uiso 1 1 calc R . .
H38B H 0.0354 0.1363 0.9764 0.171 Uiso 1 1 calc R . .
H38C H 0.1794 0.0971 0.9241 0.171 Uiso 1 1 calc R . .
C20 C -0.016(2) 0.845(2) 1.1297(16) 0.210(9) Uani 1 1 d . . .
H20A H -0.0983 0.8426 1.1786 0.316 Uiso 1 1 calc R . .
H20B H -0.0784 0.8018 1.0484 0.316 Uiso 1 1 calc R . .
H20C H 0.0621 0.9487 1.1409 0.316 Uiso 1 1 calc R . .
Se2 Se 0.46625(7) 0.69403(7) 0.99251(5) 0.07284(19) Uani 1 1 d . . .
Se1 Se 0.24623(8) 0.14548(7) 0.47279(6) 0.0776(2) Uani 1 1 d . . .
I2 I 0.46405(5) 0.94902(4) 0.83373(4) 0.08283(17) Uani 1 1 d . . .
I1 I 0.24109(5) 0.37236(5) 0.29076(5) 0.09388(19) Uani 1 1 d . . .



#----------------------------------------------------------------------------#
#                   MOLECULAR GEOMETRY                                       #
#----------------------------------------------------------------------------#

_geom_special_details            
;
 All s.u.'s (except the s.u. in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell s.u.'s are taken
 into account individually in the estimation of s.u.'s in distances, angles
 and torsion angles; correlations between s.u.'s in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell s.u.'s is used for estimating s.u.'s 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
C7 C12 1.397(8) . ?
C7 C8 1.423(9) . ?
C7 C6 1.452(8) . ?
C12 C11 1.390(8) . ?
C12 C13 1.469(9) . ?
C37 C32 1.415(8) . ?
C37 C36 1.428(8) . ?
C37 C24 1.447(7) . ?
C31 C26 1.410(8) . ?
C31 C30 1.430(8) . ?
C31 C32 1.444(9) . ?
C11 C10 1.367(10) . ?
C26 C27 1.400(9) . ?
C26 C25 1.453(7) . ?
C24 C25 1.358(8) . ?
C24 Se2 1.928(5) . ?
C19 C16 1.492(10) . ?
C27 C28 1.356(9) . ?
C8 C9 1.337(10) . ?
C25 I2 2.107(5) . ?
C13 C14 1.397(8) . ?
C13 C18 1.410(8) . ?
C30 C29 1.339(10) . ?
C35 C36 1.348(10) . ?
C35 C34 1.402(11) . ?
C35 C38 1.496(12) . ?
C18 C17 1.410(8) . ?
C18 C5 1.443(8) . ?
C5 C6 1.342(8) . ?
C5 Se1 1.929(5) . ?
C32 C33 1.396(9) . ?
C16 C15 1.382(10) . ?
C16 C17 1.387(9) . ?
C22 C23 1.314(16) . ?
C22 C21 1.498(15) . ?
C6 I1 2.110(5) . ?
C21 C20 1.395(18) . ?
C15 C14 1.340(9) . ?
C3 C4 1.487(10) . ?
C3 C2 1.534(10) . ?
C28 C29 1.370(11) . ?
C33 C34 1.360(10) . ?
C4 Se1 1.959(8) . ?
C9 C10 1.378(12) . ?
C2 C1 1.513(12) . ?
C23 Se2 1.902(10) . ?

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
C12 C7 C8 117.1(6) . . ?
C12 C7 C6 119.7(5) . . ?
C8 C7 C6 123.3(6) . . ?
C11 C12 C7 119.5(6) . . ?
C11 C12 C13 121.7(6) . . ?
C7 C12 C13 118.8(5) . . ?
C32 C37 C36 117.7(5) . . ?
C32 C37 C24 120.3(5) . . ?
C36 C37 C24 122.1(5) . . ?
C26 C31 C30 116.7(6) . . ?
C26 C31 C32 120.9(5) . . ?
C30 C31 C32 122.3(6) . . ?
C10 C11 C12 121.3(7) . . ?
C27 C26 C31 118.8(5) . . ?
C27 C26 C25 123.4(5) . . ?
C31 C26 C25 117.8(5) . . ?
C25 C24 C37 119.7(5) . . ?
C25 C24 Se2 120.9(4) . . ?
C37 C24 Se2 119.4(4) . . ?
C28 C27 C26 121.5(6) . . ?
C9 C8 C7 122.3(7) . . ?
C24 C25 C26 122.3(5) . . ?
C24 C25 I2 120.3(4) . . ?
C26 C25 I2 117.4(4) . . ?
C14 C13 C18 117.8(5) . . ?
C14 C13 C12 122.6(5) . . ?
C18 C13 C12 119.5(5) . . ?
C29 C30 C31 122.5(6) . . ?
C36 C35 C34 118.7(7) . . ?
C36 C35 C38 122.3(8) . . ?
C34 C35 C38 118.9(7) . . ?
C17 C18 C13 117.6(5) . . ?
C17 C18 C5 122.6(5) . . ?
C13 C18 C5 119.7(5) . . ?
C6 C5 C18 120.5(5) . . ?
C6 C5 Se1 120.6(4) . . ?
C18 C5 Se1 118.9(4) . . ?
C33 C32 C37 118.4(6) . . ?
C33 C32 C31 122.7(6) . . ?
C37 C32 C31 118.8(5) . . ?
C15 C16 C17 116.8(6) . . ?
C15 C16 C19 121.9(6) . . ?
C17 C16 C19 121.2(7) . . ?
C23 C22 C21 118.3(14) . . ?
C5 C6 C7 121.7(5) . . ?
C5 C6 I1 120.5(4) . . ?
C7 C6 I1 117.8(4) . . ?
C20 C21 C22 105.4(14) . . ?
C16 C17 C18 123.1(6) . . ?
C14 C15 C16 121.8(6) . . ?
C15 C14 C13 122.7(6) . . ?
C35 C36 C37 122.6(6) . . ?
C4 C3 C2 112.4(6) . . ?
C27 C28 C29 120.6(7) . . ?
C34 C33 C32 121.9(6) . . ?
C3 C4 Se1 114.9(5) . . ?
C8 C9 C10 120.1(7) . . ?
C30 C29 C28 119.8(6) . . ?
C11 C10 C9 119.8(7) . . ?
C1 C2 C3 111.9(6) . . ?
C22 C23 Se2 125.0(10) . . ?
C33 C34 C35 120.6(6) . . ?
C23 Se2 C24 98.6(3) . . ?
C5 Se1 C4 98.5(3) . . ?

# END of CIF
_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: DMSO/CH3OH'
