# Supplementary Material (ESI) for Chemical Communications
# This journal is (c) The Royal Society of Chemistry 2009


data_global
_journal_name_full               Chem.Commun.

_journal_coden_Cambridge         0182

_publ_contact_author_name        'Jaesook Yun'
_publ_contact_author_email       JAESOOK@SKKU.EDU

_publ_section_title              
;
Bis(imidazoline-2-thione)-copper(I) catalyzed
regioselective boron addition to internal alkynes
;
loop_
_publ_author_name
'Jaesook Yun'
'Kwonho Jang'
'Il Jung'
'Hye Kim'
'Eun Lee'
'Seung Son'
'Kihyun Yoo'

# Attachment 'IMS-CIF.txt'

data_yjscu
_database_code_depnum_ccdc_archive 'CCDC 747950'
#TrackingRef 'IMS-CIF.txt'

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C10 H16 Cl Cu N4 S2'
_chemical_formula_sum            'C10 H16 Cl Cu N4 S2'
_chemical_formula_weight         355.38

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'
Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cu Cu 0.3201 1.2651 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 '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  '-C2 yc'

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                   10.437(2)
_cell_length_b                   9.403(2)
_cell_length_c                   16.115(3)
_cell_angle_alpha                90.00
_cell_angle_beta                 106.320(14)
_cell_angle_gamma                90.00
_cell_volume                     1517.7(6)
_cell_formula_units_Z            4
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    ?
_cell_measurement_theta_min      ?
_cell_measurement_theta_max      ?

_exptl_crystal_description       cubic
_exptl_crystal_colour            'pale yellow'
_exptl_crystal_size_max          0.25
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.20
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.555
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             728
_exptl_absorpt_coefficient_mu    1.878
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.644
_exptl_absorpt_correction_T_max  0.687
_exptl_absorpt_process_details   ?

_exptl_special_details           
;
?
;

_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Bruker P4'
_diffrn_measurement_method       '\w scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            5923
_diffrn_reflns_av_R_equivalents  0.0284
_diffrn_reflns_av_sigmaI/netI    0.0361
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_theta_min         2.63
_diffrn_reflns_theta_max         28.30
_reflns_number_total             1838
_reflns_number_gt                1285
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Bruker XSCANS'
_computing_cell_refinement       'Bruker XSCANS'
_computing_data_reduction        'Bruker SHELXTL'
_computing_structure_solution    'Bruker SHELXTL'
_computing_structure_refinement  'Bruker SHELXTL'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'

_refine_special_details          
;
Refinement of F^2^ against ALL reflections. The weighted R-factor wR and
goodness of fit S are based on F^2^, conventional R-factors R are based
on F, with F set to zero for negative F^2^. The threshold expression of
F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is
not relevant to the choice of reflections for refinement. R-factors based
on F^2^ 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/[\s^2^(Fo^2^)+(0.0377P)^2^+0.6572P] where P=(Fo^2^+2Fc^2^)/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         1838
_refine_ls_number_parameters     83
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0620
_refine_ls_R_factor_gt           0.0349
_refine_ls_wR_factor_ref         0.0855
_refine_ls_wR_factor_gt          0.0757
_refine_ls_goodness_of_fit_ref   1.021
_refine_ls_restrained_S_all      1.021
_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
Cu2 Cu 0.5000 0.21723(5) 0.2500 0.05044(18) Uani 1 2 d S . .
S2 S 0.46608(8) 0.33950(8) 0.36079(4) 0.0559(2) Uani 1 1 d . . .
Cl3 Cl 0.5000 -0.02113(11) 0.2500 0.0618(3) Uani 1 2 d S . .
N2 N 0.4500(2) 0.1940(2) 0.50415(12) 0.0425(5) Uani 1 1 d . . .
C5 C 0.4022(2) 0.2209(3) 0.41894(15) 0.0389(6) Uani 1 1 d . . .
C3 C 0.3693(3) 0.0965(3) 0.52864(17) 0.0528(7) Uani 1 1 d . . .
H3 H 0.3805 0.0609 0.5841 0.063 Uiso 1 1 calc R . .
N1 N 0.29232(19) 0.1398(2) 0.39061(13) 0.0428(5) Uani 1 1 d . . .
C2 C 0.2720(3) 0.0626(3) 0.45813(18) 0.0523(7) Uani 1 1 d . . .
H2 H 0.2030 -0.0015 0.4552 0.063 Uiso 1 1 calc R . .
C4 C 0.5677(3) 0.2606(3) 0.56200(18) 0.0621(8) Uani 1 1 d . . .
H4A H 0.5816 0.2238 0.6194 0.093 Uiso 1 1 calc R . .
H4B H 0.5547 0.3616 0.5624 0.093 Uiso 1 1 calc R . .
H4C H 0.6444 0.2402 0.5423 0.093 Uiso 1 1 calc R . .
C1 C 0.2057(3) 0.1361(3) 0.30219(18) 0.0619(8) Uani 1 1 d . . .
H1A H 0.1344 0.0697 0.2985 0.093 Uiso 1 1 calc R . .
H1B H 0.2564 0.1070 0.2638 0.093 Uiso 1 1 calc R . .
H1C H 0.1691 0.2290 0.2860 0.093 Uiso 1 1 calc R . .

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
Cu2 0.0633(3) 0.0526(3) 0.0392(3) 0.000 0.0205(2) 0.000
S2 0.0860(6) 0.0429(4) 0.0478(4) -0.0089(3) 0.0338(4) -0.0169(4)
Cl3 0.0874(8) 0.0475(6) 0.0479(5) 0.000 0.0148(5) 0.000
N2 0.0502(12) 0.0419(13) 0.0357(10) -0.0053(9) 0.0128(9) 0.0016(10)
C5 0.0483(14) 0.0341(14) 0.0382(12) -0.0061(10) 0.0188(11) 0.0008(12)
C3 0.0691(18) 0.0494(17) 0.0462(15) 0.0106(13) 0.0263(14) 0.0059(15)
N1 0.0435(12) 0.0426(12) 0.0429(11) -0.0026(10) 0.0131(9) -0.0003(10)
C2 0.0566(17) 0.0449(17) 0.0619(18) 0.0049(13) 0.0276(15) -0.0024(13)
C4 0.068(2) 0.063(2) 0.0480(16) -0.0118(14) 0.0049(14) -0.0030(15)
C1 0.0559(17) 0.069(2) 0.0528(17) -0.0052(15) 0.0017(14) -0.0053(15)

_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
Cu2 S2 2.2339(8) . ?
Cu2 S2 2.2339(8) 2_655 ?
Cu2 Cl3 2.2412(12) . ?
S2 C5 1.708(2) . ?
N2 C5 1.346(3) . ?
N2 C3 1.376(3) . ?
N2 C4 1.459(3) . ?
C5 N1 1.346(3) . ?
C3 C2 1.333(4) . ?
N1 C2 1.373(3) . ?
N1 C1 1.458(3) . ?

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
S2 Cu2 S2 118.05(4) . 2_655 ?
S2 Cu2 Cl3 120.98(2) . . ?
S2 Cu2 Cl3 120.98(2) 2_655 . ?
C5 S2 Cu2 106.03(8) . . ?
C5 N2 C3 109.7(2) . . ?
C5 N2 C4 125.1(2) . . ?
C3 N2 C4 125.2(2) . . ?
N1 C5 N2 106.0(2) . . ?
N1 C5 S2 127.63(18) . . ?
N2 C5 S2 126.3(2) . . ?
C2 C3 N2 107.2(2) . . ?
C5 N1 C2 109.7(2) . . ?
C5 N1 C1 125.5(2) . . ?
C2 N1 C1 124.7(2) . . ?
C3 C2 N1 107.4(2) . . ?

_diffrn_measured_fraction_theta_max 0.968
_diffrn_reflns_theta_full        28.30
_diffrn_measured_fraction_theta_full 0.968
_refine_diff_density_max         0.306
_refine_diff_density_min         -0.310
_refine_diff_density_rms         0.057