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

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#
#                 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
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#  data retrieval see:
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#  from this site to visualise CIF-encoded structures and 
#  to carry out CIF format checking respectively.
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data_sw100891

_audit_creation_method           SHELXL-97
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_formula_moiety         'C12 H17 B O2 Se'
_chemical_formula_sum            'C12 H17 B O2 Se'
_exptl_crystal_recrystallization_method Et2O
_chemical_melting_point          ?

_exptl_crystal_description       Irregular
_exptl_crystal_colour            Colourless

_diffrn_ambient_temperature      213(1)
_chemical_formula_weight         283.03

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'
B B 0.0013 0.0007 '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           orthorhombic
_symmetry_space_group_name_H-M   'P b c a'
_symmetry_space_group_name_Hall  '-P 2ac 2ab'
_symmetry_int_tables_number      61
_chemical_absolute_configuration ?

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

_cell_length_a                   12.6814(12)
_cell_length_b                   13.1877(13)
_cell_length_c                   16.1788(16)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_volume                     2705.7(5)
_cell_formula_units_Z            8
_cell_measurement_temperature    213(1)
_cell_measurement_reflns_used    5892
_cell_measurement_theta_min      2.558
_cell_measurement_theta_max      26.9975
_exptl_crystal_size_max          0.30
_exptl_crystal_size_mid          0.25
_exptl_crystal_size_min          0.15
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.390
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1152
_exptl_absorpt_coefficient_mu    2.759
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.4916
_exptl_absorpt_correction_T_max  0.6824
_exptl_absorpt_process_details   'SADABS (Sheldrick, 2008)'

_exptl_special_details           
; 
Crystal decay was monitored by repeating the initial 50 frames
at the end of the data collection and analyzing duplicate
reflections
;
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'fine-focus sealed tube'
_diffrn_source_type              K760
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Bruker AXS SMART1000/P4'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         0
_diffrn_standards_interval_count 0
_diffrn_standards_interval_time  0
_diffrn_standards_decay_%        0
_diffrn_reflns_number            17722
_diffrn_reflns_av_R_equivalents  0.0404
_diffrn_reflns_av_sigmaI/netI    0.0304
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_theta_min         2.52
_diffrn_reflns_theta_max         27.50
_reflns_number_total             3075
_reflns_number_gt                2104
_reflns_threshold_expression     'I > 2σ(I)'

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

_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)+(0.0316P)²+1.8528P] 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         3075
_refine_ls_number_parameters     149
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0630
_refine_ls_R_factor_gt           0.0331
_refine_ls_wR_factor_ref         0.0840
_refine_ls_wR_factor_gt          0.0712
_refine_ls_goodness_of_fit_ref   1.027
_refine_ls_restrained_S_all      1.027
_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
Se1 Se 0.45254(2) 0.20705(2) 0.472741(18) 0.05035(12) Uani 1 1 d . . .
B1 B 0.5228(2) 0.1690(2) 0.37010(18) 0.0378(7) Uani 1 1 d . . .
O1 O 0.49461(15) 0.09318(14) 0.31868(10) 0.0450(4) Uani 1 1 d . . .
O2 O 0.60716(15) 0.22360(14) 0.34569(12) 0.0517(5) Uani 1 1 d . . .
C1 C 0.3413(2) 0.10875(19) 0.48319(14) 0.0389(6) Uani 1 1 d . . .
C2 C 0.3494(2) 0.00920(19) 0.45660(16) 0.0484(7) Uani 1 1 d . . .
H2 H 0.4109 -0.0133 0.4298 0.058 Uiso 1 1 calc R . .
C3 C 0.2667(3) -0.0567(2) 0.46980(17) 0.0539(8) Uani 1 1 d . . .
H3 H 0.2719 -0.1240 0.4511 0.065 Uiso 1 1 calc R . .
C4 C 0.1770(2) -0.0255(2) 0.50988(17) 0.0498(7) Uani 1 1 d . . .
H4 H 0.1210 -0.0710 0.5185 0.060 Uiso 1 1 calc R . .
C5 C 0.1698(2) 0.0735(2) 0.53751(17) 0.0480(7) Uani 1 1 d . . .
H5 H 0.1091 0.0952 0.5657 0.058 Uiso 1 1 calc R . .
C6 C 0.2513(2) 0.14035(19) 0.52379(15) 0.0424(6) Uani 1 1 d . . .
H6 H 0.2457 0.2078 0.5421 0.051 Uiso 1 1 calc R . .
C7 C 0.5797(2) 0.0858(2) 0.25674(16) 0.0441(6) Uani 1 1 d . . .
C8 C 0.6320(2) 0.1918(2) 0.26121(17) 0.0460(7) Uani 1 1 d . . .
C9 C 0.5295(3) 0.0606(3) 0.17485(19) 0.0817(12) Uani 1 1 d . . .
H9A H 0.4961 -0.0055 0.1782 0.123 Uiso 1 1 calc R . .
H9B H 0.5831 0.0596 0.1321 0.123 Uiso 1 1 calc R . .
H9C H 0.4768 0.1114 0.1616 0.123 Uiso 1 1 calc R . .
C10 C 0.6503(3) 0.0005(2) 0.2857(2) 0.0748(10) Uani 1 1 d . . .
H10A H 0.6828 0.0191 0.3379 0.112 Uiso 1 1 calc R . .
H10B H 0.7048 -0.0117 0.2448 0.112 Uiso 1 1 calc R . .
H10C H 0.6087 -0.0605 0.2931 0.112 Uiso 1 1 calc R . .
C11 C 0.5796(3) 0.2696(3) 0.2049(2) 0.0853(12) Uani 1 1 d . . .
H11A H 0.5038 0.2674 0.2128 0.128 Uiso 1 1 calc R . .
H11B H 0.5961 0.2540 0.1478 0.128 Uiso 1 1 calc R . .
H11C H 0.6055 0.3368 0.2183 0.128 Uiso 1 1 calc R . .
C12 C 0.7500(3) 0.1929(3) 0.2506(3) 0.0821(12) Uani 1 1 d . . .
H12A H 0.7752 0.2623 0.2517 0.123 Uiso 1 1 calc R . .
H12B H 0.7683 0.1620 0.1982 0.123 Uiso 1 1 calc R . .
H12C H 0.7826 0.1550 0.2953 0.123 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
Se1 0.0578(2) 0.04514(17) 0.04816(18) -0.01483(12) 0.01457(14) -0.00469(14)
B1 0.0370(17) 0.0416(15) 0.0349(15) -0.0016(12) -0.0012(13) 0.0032(13)
O1 0.0468(10) 0.0531(11) 0.0350(10) -0.0077(8) 0.0045(9) -0.0097(9)
O2 0.0479(11) 0.0542(12) 0.0531(12) -0.0165(9) 0.0104(10) -0.0127(9)
C1 0.0480(15) 0.0393(13) 0.0294(13) 0.0024(10) 0.0061(12) 0.0043(12)
C2 0.0605(18) 0.0386(14) 0.0460(16) -0.0020(11) 0.0183(14) 0.0071(14)
C3 0.078(2) 0.0369(15) 0.0464(16) -0.0004(12) 0.0141(16) -0.0020(15)
C4 0.0554(18) 0.0510(17) 0.0432(16) 0.0071(13) 0.0030(14) -0.0058(14)
C5 0.0470(16) 0.0517(16) 0.0454(16) 0.0051(13) 0.0082(13) 0.0080(14)
C6 0.0528(15) 0.0363(13) 0.0381(14) 0.0018(11) 0.0072(13) 0.0078(12)
C7 0.0428(15) 0.0553(16) 0.0343(13) -0.0087(12) 0.0007(12) -0.0004(13)
C8 0.0430(15) 0.0537(17) 0.0413(15) -0.0021(12) 0.0092(13) -0.0009(13)
C9 0.082(3) 0.122(3) 0.0409(17) -0.0239(19) 0.0051(18) -0.026(2)
C10 0.088(3) 0.057(2) 0.079(2) -0.0034(18) 0.012(2) 0.018(2)
C11 0.097(3) 0.079(3) 0.080(3) 0.032(2) 0.013(2) 0.008(2)
C12 0.0463(18) 0.099(3) 0.101(3) -0.022(2) 0.0248(19) -0.016(2)

_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
Se1 C1 1.923(3) . ?
Se1 B1 1.950(3) . ?
B1 O2 1.349(4) . ?
B1 O1 1.349(3) . ?
O1 C7 1.476(3) . ?
O2 C8 1.464(3) . ?
C1 C6 1.381(4) . ?
C1 C2 1.385(3) . ?
C2 C3 1.379(4) . ?
C2 H2 0.9400 . ?
C3 C4 1.373(4) . ?
C3 H3 0.9400 . ?
C4 C5 1.383(4) . ?
C4 H4 0.9400 . ?
C5 C6 1.376(4) . ?
C5 H5 0.9400 . ?
C6 H6 0.9400 . ?
C7 C9 1.507(4) . ?
C7 C10 1.512(4) . ?
C7 C8 1.549(4) . ?
C8 C12 1.507(4) . ?
C8 C11 1.524(4) . ?
C9 H9A 0.9700 . ?
C9 H9B 0.9700 . ?
C9 H9C 0.9700 . ?
C10 H10A 0.9700 . ?
C10 H10B 0.9700 . ?
C10 H10C 0.9700 . ?
C11 H11A 0.9700 . ?
C11 H11B 0.9700 . ?
C11 H11C 0.9700 . ?
C12 H12A 0.9700 . ?
C12 H12B 0.9700 . ?
C12 H12C 0.9700 . ?

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
C1 Se1 B1 103.69(12) . . ?
O2 B1 O1 115.2(2) . . ?
O2 B1 Se1 118.3(2) . . ?
O1 B1 Se1 126.5(2) . . ?
B1 O1 C7 105.9(2) . . ?
B1 O2 C8 106.9(2) . . ?
C6 C1 C2 119.7(3) . . ?
C6 C1 Se1 116.40(19) . . ?
C2 C1 Se1 123.8(2) . . ?
C3 C2 C1 119.5(3) . . ?
C3 C2 H2 120.3 . . ?
C1 C2 H2 120.3 . . ?
C4 C3 C2 121.0(3) . . ?
C4 C3 H3 119.5 . . ?
C2 C3 H3 119.5 . . ?
C3 C4 C5 119.3(3) . . ?
C3 C4 H4 120.4 . . ?
C5 C4 H4 120.4 . . ?
C6 C5 C4 120.2(3) . . ?
C6 C5 H5 119.9 . . ?
C4 C5 H5 119.9 . . ?
C5 C6 C1 120.3(2) . . ?
C5 C6 H6 119.9 . . ?
C1 C6 H6 119.9 . . ?
O1 C7 C9 107.6(2) . . ?
O1 C7 C10 105.8(2) . . ?
C9 C7 C10 111.1(3) . . ?
O1 C7 C8 102.79(19) . . ?
C9 C7 C8 114.9(3) . . ?
C10 C7 C8 113.8(2) . . ?
O2 C8 C12 108.5(3) . . ?
O2 C8 C11 105.7(2) . . ?
C12 C8 C11 111.0(3) . . ?
O2 C8 C7 102.1(2) . . ?
C12 C8 C7 115.3(3) . . ?
C11 C8 C7 113.1(3) . . ?
C7 C9 H9A 109.5 . . ?
C7 C9 H9B 109.5 . . ?
H9A C9 H9B 109.5 . . ?
C7 C9 H9C 109.5 . . ?
H9A C9 H9C 109.5 . . ?
H9B C9 H9C 109.5 . . ?
C7 C10 H10A 109.5 . . ?
C7 C10 H10B 109.5 . . ?
H10A C10 H10B 109.5 . . ?
C7 C10 H10C 109.5 . . ?
H10A C10 H10C 109.5 . . ?
H10B C10 H10C 109.5 . . ?
C8 C11 H11A 109.5 . . ?
C8 C11 H11B 109.5 . . ?
H11A C11 H11B 109.5 . . ?
C8 C11 H11C 109.5 . . ?
H11A C11 H11C 109.5 . . ?
H11B C11 H11C 109.5 . . ?
C8 C12 H12A 109.5 . . ?
C8 C12 H12B 109.5 . . ?
H12A C12 H12B 109.5 . . ?
C8 C12 H12C 109.5 . . ?
H12A C12 H12C 109.5 . . ?
H12B C12 H12C 109.5 . . ?

_diffrn_measured_fraction_theta_max 0.990
_diffrn_reflns_theta_full        25.00
_diffrn_measured_fraction_theta_full 1.000
_refine_diff_density_max         0.673
_refine_diff_density_min         -0.509
_refine_diff_density_rms         0.058
_database_code_depnum_ccdc_archive 'CCDC 991941'
