# Electronic Supplementary Material (ESI) for Chemical Communications
# This journal is © The Royal Society of Chemistry 2013


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#                 Cambridge Crystallographic Data Centre
#                                CCDC 
# 
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# 
#  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. 
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#  fide research purposes only. It may contain copyright material 
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data_BeT2-a
_database_code_depnum_ccdc_archive 'CCDC 921520'
#TrackingRef '17157_web_deposit_cif_file_0_JunYeobLee_1358992055.BeTh.cif'
_audit_creation_method           SHELXTL
_chemical_name_systematic        
;
?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C18 H12 Be N2 O2 S2'
_chemical_formula_sum            'C18 H12 Be N2 O2 S2'
_chemical_formula_weight         361.43
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'
Be Be 0.0005 0.0002 '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'
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           Orthorhombic
_symmetry_space_group_name_H-M   Aba2
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, z'
'x+1/2, -y+1/2, z'
'-x+1/2, y+1/2, z'
'x, y+1/2, z+1/2'
'-x, -y+1/2, z+1/2'
'x+1/2, -y+1, z+1/2'
'-x+1/2, y+1, z+1/2'
_cell_length_a                   10.2336(15)
_cell_length_b                   14.137(2)
_cell_length_c                   11.2663(17)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_volume                     1629.9(4)
_cell_formula_units_Z            4
_cell_measurement_temperature    200(2)
_cell_measurement_reflns_used    4016
_cell_measurement_theta_min      2.31
_cell_measurement_theta_max      28.28
_exptl_crystal_description       block
_exptl_crystal_colour            'pale yellow'
_exptl_crystal_size_max          0.43
_exptl_crystal_size_mid          0.37
_exptl_crystal_size_min          0.13
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.473
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             744
_exptl_absorpt_coefficient_mu    0.340
_exptl_absorpt_correction_type   Multi-scan
_exptl_absorpt_correction_T_min  0.8675
_exptl_absorpt_correction_T_max  0.9571
_exptl_absorpt_process_details   'Bruker SADABS'
_exptl_special_details           
;
?
;
_diffrn_ambient_temperature      200(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  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            5372
_diffrn_reflns_av_R_equivalents  0.0158
_diffrn_reflns_av_sigmaI/netI    0.0196
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_theta_min         3.05
_diffrn_reflns_theta_max         28.31
_reflns_number_total             1888
_reflns_number_gt                1693
_reflns_threshold_expression     >2sigma(I)
_computing_data_collection       'Bruker SMART'
_computing_cell_refinement       'Bruker SMART'
_computing_data_reduction        'Bruker SAINT'
_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^)+(0.1097P)^2^+2.6942P] 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_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.03(19)
_refine_ls_number_reflns         1888
_refine_ls_number_parameters     114
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0603
_refine_ls_R_factor_gt           0.0455
_refine_ls_wR_factor_ref         0.2027
_refine_ls_wR_factor_gt          0.1338
_refine_ls_goodness_of_fit_ref   1.232
_refine_ls_restrained_S_all      1.232
_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
Be1 Be 0.5000 0.0000 0.4570(7) 0.0312(14) Uani 1 2 d S . .
O1 O 0.5431(3) 0.08812(19) 0.5327(3) 0.0340(6) Uani 1 1 d . . .
N1 N 0.3713(3) 0.0416(2) 0.3695(3) 0.0304(7) Uani 1 1 d . . .
C1 C 0.2984(4) -0.0104(3) 0.2885(5) 0.0392(9) Uani 1 1 d . . .
H1 H 0.3205 -0.0734 0.2671 0.047 Uiso 1 1 calc R . .
C2 C 0.1944(4) 0.0348(4) 0.2425(4) 0.0486(12) Uani 1 1 d . . .
H2 H 0.1339 0.0081 0.1880 0.058 Uiso 1 1 calc R . .
S1 S 0.18768(9) 0.14829(8) 0.29765(13) 0.0449(3) Uani 1 1 d . . .
C3 C 0.3261(4) 0.1280(3) 0.3828(4) 0.0311(8) Uani 1 1 d . . .
C4 C 0.3879(4) 0.2004(3) 0.4562(4) 0.0314(8) Uani 1 1 d . . .
C5 C 0.3414(5) 0.2932(3) 0.4551(4) 0.0432(10) Uani 1 1 d . . .
H5 H 0.2677 0.3087 0.4076 0.052 Uiso 1 1 calc R . .
C6 C 0.4010(6) 0.3631(3) 0.5223(6) 0.0508(12) Uani 1 1 d . . .
H6 H 0.3700 0.4264 0.5206 0.061 Uiso 1 1 calc R . .
C7 C 0.5073(5) 0.3382(3) 0.5921(5) 0.0434(11) Uani 1 1 d . . .
H7 H 0.5489 0.3853 0.6387 0.052 Uiso 1 1 calc R . .
C8 C 0.5544(4) 0.2464(3) 0.5955(4) 0.0367(8) Uani 1 1 d . . .
H8 H 0.6275 0.2318 0.6442 0.044 Uiso 1 1 calc R . .
C9 C 0.4962(4) 0.1750(3) 0.5286(4) 0.0315(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
Be1 0.028(3) 0.031(3) 0.035(4) 0.000 0.000 -0.002(3)
O1 0.0339(14) 0.0349(13) 0.0332(14) -0.0012(12) -0.0102(12) 0.0038(11)
N1 0.0300(15) 0.0359(16) 0.0253(16) -0.0014(12) -0.0030(12) -0.0068(12)
C1 0.0408(19) 0.0392(19) 0.037(2) -0.012(2) -0.0048(19) -0.0132(15)
C2 0.037(2) 0.076(3) 0.032(2) -0.007(2) -0.0089(17) -0.020(2)
S1 0.0303(5) 0.0612(7) 0.0431(6) 0.0011(6) -0.0118(5) 0.0025(4)
C3 0.0237(17) 0.0378(19) 0.032(2) -0.0003(15) -0.0042(14) -0.0012(14)
C4 0.0234(16) 0.0361(17) 0.0348(19) -0.0033(14) -0.0016(13) 0.0011(14)
C5 0.040(2) 0.041(2) 0.048(3) 0.0001(19) -0.0042(19) 0.0125(18)
C6 0.061(3) 0.037(2) 0.054(3) -0.0105(19) -0.005(2) 0.014(2)
C7 0.047(3) 0.036(2) 0.047(3) 0.0004(19) -0.001(2) -0.0059(18)
C8 0.0324(18) 0.041(2) 0.0363(19) -0.0057(16) -0.0077(17) -0.0004(17)
C9 0.0319(19) 0.0271(17) 0.035(2) -0.0020(16) 0.0004(15) -0.0010(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
Be1 O1 1.573(5) . ?
Be1 O1 1.573(5) 2_655 ?
Be1 N1 1.747(5) . ?
Be1 N1 1.747(5) 2_655 ?
O1 C9 1.319(5) . ?
N1 C3 1.314(5) . ?
N1 C1 1.389(5) . ?
C1 C2 1.345(7) . ?
C2 S1 1.722(6) . ?
S1 C3 1.734(4) . ?
C3 C4 1.461(5) . ?
C4 C5 1.395(6) . ?
C4 C9 1.423(6) . ?
C5 C6 1.386(7) . ?
C6 C7 1.388(8) . ?
C7 C8 1.385(6) . ?
C8 C9 1.393(6) . ?
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
O1 Be1 O1 114.3(5) . 2_655 ?
O1 Be1 N1 104.54(14) . . ?
O1 Be1 N1 111.17(15) 2_655 . ?
O1 Be1 N1 111.17(15) . 2_655 ?
O1 Be1 N1 104.54(14) 2_655 2_655 ?
N1 Be1 N1 111.3(5) . 2_655 ?
C9 O1 Be1 128.0(3) . . ?
C3 N1 C1 112.1(3) . . ?
C3 N1 Be1 120.9(3) . . ?
C1 N1 Be1 126.7(3) . . ?
C2 C1 N1 115.3(4) . . ?
C1 C2 S1 109.5(3) . . ?
C2 S1 C3 90.7(2) . . ?
N1 C3 C4 124.3(3) . . ?
N1 C3 S1 112.3(3) . . ?
C4 C3 S1 123.4(3) . . ?
C5 C4 C9 120.6(4) . . ?
C5 C4 C3 120.4(4) . . ?
C9 C4 C3 119.0(3) . . ?
C6 C5 C4 121.0(4) . . ?
C5 C6 C7 118.3(4) . . ?
C8 C7 C6 121.8(5) . . ?
C7 C8 C9 121.0(4) . . ?
O1 C9 C8 120.0(4) . . ?
O1 C9 C4 122.6(4) . . ?
C8 C9 C4 117.4(4) . . ?
_diffrn_measured_fraction_theta_max 0.966
_diffrn_reflns_theta_full        28.31
_diffrn_measured_fraction_theta_full 0.966
_refine_diff_density_max         0.410
_refine_diff_density_min         -0.575
_refine_diff_density_rms         0.093