# Supplementary Material (ESI) for Chemical Communications
# This journal is (c) The Royal Society of Chemistry 2010


data_global

_journal_coden_Cambridge         182

loop_
_publ_author_name
'Lepeltier, Marc'
'Lukoyanova, Olena'
'Jacobson, Alex'
'Jeeva, Shehzad'
'Perepichka, Dmitrii'

_publ_contact_author_name        'Perepichka, Dmitrii'
_publ_contact_author_email       dmitrii.perepichka@mcgill.ca

_publ_section_title              
;
New azaborine-thiophene heteroacenes
;

# Attachment '- 1a.cif'

data_perep7
_database_code_depnum_ccdc_archive 'CCDC 782155'
#TrackingRef '- 1a.cif'

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C24 H16 B2 N2 S3, C3 H6 O '
_chemical_formula_sum            'C27 H22 B2 N2 O S3'
_chemical_formula_weight         508.27
_chemical_compound_source        'Synthesized by the authors. See text'

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 '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 0.0090 0.0039 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.3331 0.5567 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           Monoclinic
_symmetry_space_group_name_H-M   P2/c
_symmetry_space_group_name_hall  '-P 2yc'

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

_cell_length_a                   22.2919(7)
_cell_length_b                   11.7457(4)
_cell_length_c                   9.6074(4)
_cell_angle_alpha                90.00
_cell_angle_beta                 101.837(2)
_cell_angle_gamma                90.00
_cell_volume                     2462.05(15)
_cell_formula_units_Z            4
_cell_measurement_temperature    150
_cell_measurement_reflns_used    16607
_cell_measurement_theta_min      7.5
_cell_measurement_theta_max      133.4

_exptl_crystal_description       chunk
_exptl_crystal_colour            Colorless
_exptl_crystal_size_max          0.16
_exptl_crystal_size_mid          0.05
_exptl_crystal_size_min          0.04
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.371
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1056
_exptl_absorpt_coefficient_mu    2.938
_exptl_absorpt_correction_Type   multi-scan
_exptl_absorpt_correction_T_min  0.4500
_exptl_absorpt_correction_T_max  0.9200
_exptl_absorpt_process_details   'Sadabs (Sheldrick,1996)'

_diffrn_ambient_temperature      150
_diffrn_radiation_wavelength     1.54178
_diffrn_radiation_type           CuK\a
_diffrn_radiation_source         'Micro source'
_diffrn_radiation_monochromator  'Helios optics'
_diffrn_measurement_device_type  'Bruker Microstar'
_diffrn_measurement_method       \w
_diffrn_detector_area_resol_mean 5.5
_diffrn_standards_number         5
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        0.00
_diffrn_reflns_number            33448
_diffrn_reflns_av_R_equivalents  0.055
_diffrn_reflns_av_sigmaI/netI    0.0247
_diffrn_reflns_limit_h_min       -26
_diffrn_reflns_limit_h_max       26
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_theta_min         2.02
_diffrn_reflns_theta_max         67.17
_reflns_number_total             4015
_reflns_number_gt                3654
_reflns_threshold_expression     I>2\s(I)

_computing_data_collection       'APEX2(Bruker, 2006)'
_computing_cell_refinement       'APEX2(Bruker, 2006)'
_computing_data_reduction        'SAINT (Bruker, 2006)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 1997)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 1997)'
_computing_molecular_graphics    'SHELXTL (Bruker, 1997)'
_computing_publication_material  'UdMX (local program)'

_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^)+(0.1024P)^2^+9.8705P] 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         4015
_refine_ls_number_parameters     330
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0877
_refine_ls_R_factor_gt           0.0822
_refine_ls_wR_factor_ref         0.2192
_refine_ls_wR_factor_gt          0.2141
_refine_ls_goodness_of_fit_ref   1.096
_refine_ls_restrained_S_all      1.096
_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
S11 S 0.0000 0.66747(15) 0.2500 0.0316(5) Uani 1 2 d S . .
C11 C -0.0411(2) 0.5642(4) 0.1400(6) 0.0275(12) Uani 1 1 d . . .
C12 C -0.0246(2) 0.4552(4) 0.1864(6) 0.0235(11) Uani 1 1 d . . .
N13 N -0.05339(19) 0.3623(4) 0.1144(5) 0.0247(10) Uani 1 1 d . . .
H13 H -0.0413 0.2939 0.1455 0.030 Uiso 1 1 calc R . .
B14 B -0.1029(3) 0.3713(5) -0.0108(7) 0.0275(13) Uani 1 1 d . . .
C15 C -0.1201(2) 0.4922(5) -0.0616(7) 0.0338(14) Uani 1 1 d . . .
C16 C -0.0879(2) 0.5827(5) 0.0134(6) 0.0277(12) Uani 1 1 d . . .
S17 S -0.11141(7) 0.71366(12) -0.05886(18) 0.0374(4) Uani 1 1 d . . .
C18 C -0.1655(3) 0.6513(5) -0.1951(7) 0.0379(14) Uani 1 1 d . . .
H18 H -0.1920 0.6924 -0.2679 0.046 Uiso 1 1 calc R . .
C19 C -0.1645(3) 0.5344(5) -0.1823(7) 0.0343(13) Uani 1 1 d . . .
H19 H -0.1905 0.4857 -0.2470 0.041 Uiso 1 1 calc R . .
C141 C -0.1371(3) 0.2595(5) -0.0700(7) 0.0354(14) Uani 1 1 d . . .
C142 C -0.1685(3) 0.2506(5) -0.2159(7) 0.0350(13) Uani 1 1 d . . .
H142 H -0.1667 0.3130 -0.2779 0.042 Uiso 1 1 calc R . .
C143 C -0.2016(3) 0.1541(6) -0.2703(7) 0.0413(15) Uani 1 1 d . . .
H143 H -0.2218 0.1517 -0.3674 0.050 Uiso 1 1 calc R . .
C144 C -0.2051(3) 0.0623(6) -0.1831(8) 0.0457(17) Uani 1 1 d . . .
H144 H -0.2277 -0.0036 -0.2193 0.055 Uiso 1 1 calc R . .
C145 C -0.1748(3) 0.0674(6) -0.0408(8) 0.0434(16) Uani 1 1 d . . .
H145 H -0.1764 0.0041 0.0199 0.052 Uiso 1 1 calc R . .
C146 C -0.1420(3) 0.1657(5) 0.0133(7) 0.0338(13) Uani 1 1 d . . .
H146 H -0.1225 0.1675 0.1110 0.041 Uiso 1 1 calc R . .
S21 S 0.5000 1.17354(16) 0.2500 0.0328(5) Uani 1 2 d S . .
C21 C 0.4587(2) 1.0699(5) 0.3168(6) 0.0280(12) Uani 1 1 d . . .
C22 C 0.4752(2) 0.9611(4) 0.2870(6) 0.0259(12) Uani 1 1 d . . .
N23 N 0.44643(19) 0.8682(4) 0.3275(5) 0.0257(10) Uani 1 1 d . . .
H23 H 0.4596 0.8001 0.3101 0.031 Uiso 1 1 calc R . .
B24 B 0.3966(3) 0.8767(5) 0.3958(7) 0.0255(13) Uani 1 1 d . . .
C25 C 0.3790(2) 0.9970(5) 0.4319(6) 0.0244(11) Uani 1 1 d . . .
C26 C 0.4107(2) 1.0886(5) 0.3893(6) 0.0274(12) Uani 1 1 d . . .
S27 S 0.38567(7) 1.21870(12) 0.43511(18) 0.0390(4) Uani 1 1 d . . .
C28 C 0.3298(3) 1.1539(5) 0.5058(7) 0.0400(15) Uani 1 1 d . . .
H28 H 0.3007 1.1938 0.5472 0.048 Uiso 1 1 calc R . .
C29 C 0.3320(3) 1.0395(5) 0.4955(7) 0.0377(14) Uani 1 1 d . . .
H29 H 0.3038 0.9910 0.5289 0.045 Uiso 1 1 calc R . .
C241 C 0.3645(3) 0.7653(5) 0.4272(6) 0.0319(13) Uani 1 1 d . . .
C242 C 0.3361(3) 0.7562(6) 0.5438(7) 0.0395(15) Uani 1 1 d . . .
H242 H 0.3394 0.8180 0.6086 0.047 Uiso 1 1 calc R . .
C243 C 0.3035(3) 0.6613(6) 0.5685(8) 0.0451(17) Uani 1 1 d . . .
H243 H 0.2856 0.6583 0.6501 0.054 Uiso 1 1 calc R . .
C244 C 0.2966(3) 0.5695(6) 0.4742(8) 0.0497(19) Uani 1 1 d . . .
H244 H 0.2737 0.5044 0.4902 0.060 Uiso 1 1 calc R . .
C245 C 0.3234(3) 0.5746(6) 0.3586(8) 0.0471(18) Uani 1 1 d . . .
H245 H 0.3195 0.5123 0.2944 0.057 Uiso 1 1 calc R . .
C246 C 0.3564(3) 0.6707(5) 0.3345(7) 0.0352(14) Uani 1 1 d . . .
H246 H 0.3741 0.6727 0.2526 0.042 Uiso 1 1 calc R . .
C31 C 0.5000 0.5415(7) 0.2500 0.048(3) Uani 1 2 d S . .
O31 O 0.5000 0.6445(5) 0.2500 0.0520(18) Uani 1 2 d S A .
C32 C 0.447(2) 0.474(4) 0.170(4) 0.076(11) Uani 0.50 1 d P A -1
H32A H 0.4151 0.5256 0.1225 0.113 Uiso 0.50 1 calc PR A -1
H32B H 0.4310 0.4253 0.2369 0.113 Uiso 0.50 1 calc PR A -1
H32C H 0.4611 0.4261 0.0994 0.113 Uiso 0.50 1 calc PR A -1
C33 C 0.464(2) 0.479(4) 0.120(4) 0.076(11) Uani 0.50 1 d P A -2
H33A H 0.4312 0.4349 0.1467 0.113 Uiso 0.50 1 calc PR A -2
H33B H 0.4920 0.4280 0.0826 0.113 Uiso 0.50 1 calc PR A -2
H33C H 0.4469 0.5348 0.0466 0.113 Uiso 0.50 1 calc PR A -2
C41 C 0.0000 0.0338(7) 0.2500 0.044(2) Uani 1 2 d S . .
O41 O 0.0000 0.1392(5) 0.2500 0.0551(19) Uani 1 2 d S B .
C42 C 0.052(2) -0.029(3) 0.228(3) 0.068(7) Uani 0.50 1 d P B -1
H42A H 0.0821 0.0230 0.2009 0.102 Uiso 0.50 1 calc PR B -1
H42B H 0.0391 -0.0848 0.1511 0.102 Uiso 0.50 1 calc PR B -1
H42C H 0.0707 -0.0694 0.3153 0.102 Uiso 0.50 1 calc PR B -1
C43 C 0.038(2) -0.031(3) 0.159(3) 0.068(7) Uani 0.50 1 d P B -2
H43A H 0.0105 -0.0776 0.0884 0.102 Uiso 0.50 1 calc PR B -2
H43B H 0.0677 -0.0800 0.2199 0.102 Uiso 0.50 1 calc PR B -2
H43C H 0.0595 0.0237 0.1096 0.102 Uiso 0.50 1 calc PR B -2

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
S11 0.0379(10) 0.0196(9) 0.0373(12) 0.000 0.0077(9) 0.000
C11 0.030(3) 0.025(3) 0.033(3) -0.002(2) 0.017(2) -0.003(2)
C12 0.028(2) 0.021(2) 0.024(3) 0.000(2) 0.012(2) 0.0007(19)
N13 0.026(2) 0.023(2) 0.026(3) 0.0041(18) 0.0073(19) 0.0024(17)
B14 0.024(3) 0.033(3) 0.028(4) 0.000(3) 0.012(3) 0.003(2)
C15 0.018(2) 0.028(3) 0.056(4) 0.006(3) 0.008(3) 0.001(2)
C16 0.028(3) 0.029(3) 0.029(3) -0.001(2) 0.013(2) 0.002(2)
S17 0.0422(8) 0.0286(7) 0.0418(10) 0.0104(6) 0.0093(7) 0.0044(6)
C18 0.035(3) 0.040(3) 0.038(4) 0.014(3) 0.006(3) 0.009(3)
C19 0.031(3) 0.042(3) 0.029(3) 0.003(3) 0.006(3) 0.000(2)
C141 0.033(3) 0.035(3) 0.041(4) 0.006(3) 0.015(3) 0.011(2)
C142 0.035(3) 0.036(3) 0.034(3) -0.006(3) 0.005(3) 0.005(2)
C143 0.037(3) 0.049(4) 0.035(4) -0.011(3) 0.002(3) 0.002(3)
C144 0.038(3) 0.048(4) 0.052(4) -0.021(3) 0.011(3) -0.015(3)
C145 0.045(3) 0.037(3) 0.052(4) -0.009(3) 0.018(3) -0.013(3)
C146 0.031(3) 0.036(3) 0.035(4) -0.006(3) 0.009(3) -0.005(2)
S21 0.0397(10) 0.0231(9) 0.0371(12) 0.000 0.0112(9) 0.000
C21 0.030(3) 0.030(3) 0.024(3) 0.001(2) 0.003(2) -0.004(2)
C22 0.027(2) 0.022(3) 0.026(3) -0.005(2) 0.001(2) 0.001(2)
N23 0.025(2) 0.025(2) 0.026(3) 0.0001(18) 0.0029(19) 0.0014(17)
B24 0.027(3) 0.036(3) 0.015(3) -0.003(2) 0.006(2) 0.004(2)
C25 0.024(2) 0.037(3) 0.012(3) -0.002(2) 0.004(2) 0.000(2)
C26 0.033(3) 0.029(3) 0.019(3) -0.003(2) 0.004(2) -0.001(2)
S27 0.0484(9) 0.0321(8) 0.0382(9) -0.0081(6) 0.0130(7) 0.0033(6)
C28 0.039(3) 0.047(4) 0.034(4) -0.014(3) 0.008(3) 0.006(3)
C29 0.033(3) 0.048(4) 0.032(4) -0.010(3) 0.007(3) -0.002(3)
C241 0.040(3) 0.033(3) 0.026(3) 0.010(2) 0.014(3) 0.007(2)
C242 0.033(3) 0.042(3) 0.041(4) 0.007(3) 0.003(3) 0.002(3)
C243 0.035(3) 0.061(4) 0.040(4) 0.016(3) 0.009(3) -0.005(3)
C244 0.044(4) 0.059(4) 0.045(5) 0.016(3) 0.005(3) -0.022(3)
C245 0.055(4) 0.044(4) 0.038(4) -0.003(3) -0.001(3) -0.021(3)
C246 0.036(3) 0.035(3) 0.034(3) -0.001(2) 0.007(3) -0.006(2)
C31 0.033(4) 0.023(4) 0.082(8) 0.000 -0.002(5) 0.000
O31 0.049(4) 0.026(3) 0.083(5) 0.000 0.016(4) 0.000
C32 0.09(2) 0.048(6) 0.07(3) 0.005(14) -0.024(15) -0.002(12)
C33 0.09(2) 0.048(6) 0.07(3) 0.005(14) -0.024(15) -0.002(12)
C41 0.034(4) 0.028(4) 0.070(7) 0.000 0.013(5) 0.000
O41 0.049(4) 0.021(3) 0.090(6) 0.000 0.004(4) 0.000
C42 0.081(18) 0.049(5) 0.09(2) -0.016(16) 0.051(18) 0.001(9)
C43 0.081(18) 0.049(5) 0.09(2) -0.016(16) 0.051(18) 0.001(9)

_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_site_symmetry_1
_geom_bond_site_symmetry_2
_geom_bond_distance
_geom_bond_publ_flag
S11 C11 . . 1.741(5) Y
S11 C11 . 2 1.741(5) Y
C11 C12 . . 1.380(7) Y
C11 C16 . . 1.447(8) Y
C12 N13 . . 1.378(7) Y
C12 C12 . 2 1.466(11) Y
N13 B14 . . 1.459(8) Y
N13 H13 . . 0.88 ?
B14 C15 . . 1.525(8) Y
B14 C141 . . 1.565(9) Y
C15 C16 . . 1.397(8) Y
C15 C19 . . 1.448(8) Y
C16 S17 . . 1.724(5) Y
S17 C18 . . 1.748(7) Y
C18 C19 . . 1.379(9) Y
C18 H18 . . 0.95 ?
C19 H19 . . 0.95 ?
C141 C146 . . 1.380(8) Y
C141 C142 . . 1.437(9) Y
C142 C143 . . 1.394(9) Y
C142 H142 . . 0.95 ?
C143 C144 . . 1.377(10) Y
C143 H143 . . 0.95 ?
C144 C145 . . 1.396(10) Y
C144 H144 . . 0.95 ?
C145 C146 . . 1.407(8) Y
C145 H145 . . 0.95 ?
C146 H146 . . 0.95 ?
S21 C21 . 2_655 1.727(6) Y
S21 C21 . . 1.727(6) Y
C21 C22 . . 1.376(7) Y
C21 C26 . . 1.409(8) Y
C22 N23 . . 1.362(7) Y
C22 C22 . 2_655 1.433(11) Y
N23 B24 . . 1.404(8) Y
N23 H23 . . 0.88 ?
B24 C25 . . 1.527(8) Y
B24 C241 . . 1.551(8) Y
C25 C26 . . 1.394(8) Y
C25 C29 . . 1.408(8) Y
C26 S27 . . 1.714(6) Y
S27 C28 . . 1.715(7) Y
C28 C29 . . 1.350(9) Y
C28 H28 . . 0.95 ?
C29 H29 . . 0.95 ?
C241 C242 . . 1.399(9) Y
C241 C246 . . 1.412(8) Y
C242 C243 . . 1.377(9) Y
C242 H242 . . 0.95 ?
C243 C244 . . 1.397(11) Y
C243 H243 . . 0.95 ?
C244 C245 . . 1.365(11) Y
C244 H244 . . 0.95 ?
C245 C246 . . 1.392(9) Y
C245 H245 . . 0.95 ?
C246 H246 . . 0.95 ?
C31 O31 . . 1.211(10) Y
C31 C32 . 2_655 1.49(5) Y
C31 C32 . . 1.49(5) Y
C31 C33 . . 1.52(5) Y
C31 C33 . 2_655 1.52(5) Y
C32 H32a . . 0.98 ?
C32 H32b . . 0.98 ?
C32 H32c . . 0.98 ?
C33 H33a . . 0.98 ?
C33 H33b . . 0.98 ?
C33 H33c . . 0.98 ?
C41 O41 . . 1.238(10) Y
C41 C42 . . 1.43(4) Y
C41 C42 . 2 1.43(4) Y
C41 C43 . . 1.54(4) Y
C41 C43 . 2 1.54(4) Y
C42 H42a . . 0.98 ?
C42 H42b . . 0.98 ?
C42 H42c . . 0.98 ?
C43 H43a . . 0.98 ?
C43 H43b . . 0.98 ?
C43 H43c . . 0.98 ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_2
_geom_angle_site_symmetry_3
_geom_angle
_geom_angle_publ_flag
C11 S11 C11 . . 2 91.6(4) Y
C12 C11 C16 . . . 120.6(5) Y
C12 C11 S11 . . . 112.2(4) Y
C16 C11 S11 . . . 127.2(4) Y
N13 C12 C11 . . . 120.5(5) Y
N13 C12 C12 . . 2 127.6(3) Y
C11 C12 C12 . . 2 111.9(3) Y
C12 N13 B14 . . . 123.4(4) Y
C12 N13 H13 . . . 118.3 ?
B14 N13 H13 . . . 118.3 ?
N13 B14 C15 . . . 115.4(5) Y
N13 B14 C141 . . . 117.9(5) Y
C15 B14 C141 . . . 126.4(5) Y
C16 C15 C19 . . . 110.3(5) Y
C16 C15 B14 . . . 118.3(5) Y
C19 C15 B14 . . . 131.3(5) Y
C15 C16 C11 . . . 121.6(5) Y
C15 C16 S17 . . . 112.9(4) Y
C11 C16 S17 . . . 125.5(4) Y
C16 S17 C18 . . . 92.0(3) Y
C19 C18 S17 . . . 110.7(4) Y
C19 C18 H18 . . . 124.6 ?
S17 C18 H18 . . . 124.6 ?
C18 C19 C15 . . . 114.1(5) Y
C18 C19 H19 . . . 123 ?
C15 C19 H19 . . . 123 ?
C146 C141 C142 . . . 115.3(6) Y
C146 C141 B14 . . . 123.3(6) Y
C142 C141 B14 . . . 121.3(5) Y
C143 C142 C141 . . . 122.6(6) Y
C143 C142 H142 . . . 118.7 ?
C141 C142 H142 . . . 118.7 ?
C144 C143 C142 . . . 120.0(6) Y
C144 C143 H143 . . . 120 ?
C142 C143 H143 . . . 120 ?
C143 C144 C145 . . . 119.1(6) Y
C143 C144 H144 . . . 120.5 ?
C145 C144 H144 . . . 120.5 ?
C144 C145 C146 . . . 120.4(6) Y
C144 C145 H145 . . . 119.8 ?
C146 C145 H145 . . . 119.8 ?
C141 C146 C145 . . . 122.6(6) Y
C141 C146 H146 . . . 118.7 ?
C145 C146 H146 . . . 118.7 ?
C21 S21 C21 2_655 . . 90.4(4) Y
C22 C21 C26 . . . 120.7(5) Y
C22 C21 S21 . . . 113.1(5) Y
C26 C21 S21 . . . 126.2(4) Y
N23 C22 C21 . . . 121.6(5) Y
N23 C22 C22 . . 2_655 126.7(3) Y
C21 C22 C22 . . 2_655 111.7(3) Y
C22 N23 B24 . . . 122.7(5) Y
C22 N23 H23 . . . 118.7 ?
B24 N23 H23 . . . 118.7 ?
N23 B24 C25 . . . 115.9(5) Y
N23 B24 C241 . . . 118.2(5) Y
C25 B24 C241 . . . 125.9(5) Y
C26 C25 C29 . . . 108.8(5) Y
C26 C25 B24 . . . 118.5(5) Y
C29 C25 B24 . . . 132.5(5) Y
C25 C26 C21 . . . 120.5(5) Y
C25 C26 S27 . . . 113.6(4) Y
C21 C26 S27 . . . 125.9(4) Y
C26 S27 C28 . . . 90.4(3) Y
C29 C28 S27 . . . 111.9(5) Y
C29 C28 H28 . . . 124.1 ?
S27 C28 H28 . . . 124.1 ?
C28 C29 C25 . . . 115.2(6) Y
C28 C29 H29 . . . 122.4 ?
C25 C29 H29 . . . 122.4 ?
C242 C241 C246 . . . 115.1(6) Y
C242 C241 B24 . . . 121.6(6) Y
C246 C241 B24 . . . 123.1(5) Y
C243 C242 C241 . . . 122.8(7) Y
C243 C242 H242 . . . 118.6 ?
C241 C242 H242 . . . 118.6 ?
C242 C243 C244 . . . 120.2(7) Y
C242 C243 H243 . . . 119.9 ?
C244 C243 H243 . . . 119.9 ?
C245 C244 C243 . . . 119.1(6) Y
C245 C244 H244 . . . 120.5 ?
C243 C244 H244 . . . 120.5 ?
C244 C245 C246 . . . 120.3(7) Y
C244 C245 H245 . . . 119.8 ?
C246 C245 H245 . . . 119.8 ?
C245 C246 C241 . . . 122.4(6) Y
C245 C246 H246 . . . 118.8 ?
C241 C246 H246 . . . 118.8 ?
O31 C31 C32 . . 2_655 122.10(18) Y
O31 C31 C32 . . . 122.10(18) Y
C32 C31 C32 2_655 . . 116(4) Y
O31 C31 C33 . . . 118.70(16) Y
C32 C31 C33 2_655 . . 112.80(11) Y
O31 C31 C33 . . 2_655 118.70(16) Y
C32 C31 C33 . . 2_655 112.80(11) Y
C33 C31 C33 . . 2_655 123(3) Y
C31 C32 H32A . . . 109.5 ?
C31 C32 H32B . . . 109.5 ?
C31 C32 H32C . . . 109.5 ?
C31 C33 H33A . . . 109.5 ?
C31 C33 H33B . . . 109.5 ?
H33A C33 H33B . . . 109.5 ?
C31 C33 H33C . . . 109.5 ?
H33A C33 H33C . . . 109.5 ?
H33B C33 H33C . . . 109.5 ?
O41 C41 C42 . . . 121.20(17) Y
O41 C41 C42 . . 2 121.20(17) Y
C42 C41 C42 . . 2 118(3) Y
O41 C41 C43 . . . 119.60(16) Y
C42 C41 C43 2 . . 112.8(1) Y
O41 C41 C43 . . 2 119.60(16) Y
C42 C41 C43 . . 2 112.8(1) Y
C43 C41 C43 . . 2 121(3) Y
C41 C42 H42A . . . 109.5 ?
C41 C42 H42B . . . 109.5 ?
C41 C42 H42C . . . 109.5 ?
C41 C43 H43A . . . 109.5 ?
C41 C43 H43B . . . 109.5 ?
H43A C43 H43B . . . 109.5 ?
C41 C43 H43C . . . 109.5 ?
H43A C43 H43C . . . 109.5 ?
H43B C43 H43C . . . 109.5 ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion
_geom_torsion_publ_flag
C11 S11 C11 C12 2 . . . 0.7(3) Y
C11 S11 C11 C16 2 . . . -179.5(6) Y
C16 C11 C12 N13 . . . . -1.4(8) Y
S11 C11 C12 N13 . . . . 178.4(4) Y
C16 C11 C12 C12 . . . 2 178.4(6) Y
S11 C11 C12 C12 . . . 2 -1.8(7) Y
C11 C12 N13 B14 . . . . -1.3(8) Y
C12 C12 N13 B14 2 . . . 178.9(6) Y
C12 N13 B14 C15 . . . . 1.9(8) Y
C12 N13 B14 C141 . . . . -172.2(5) Y
N13 B14 C15 C16 . . . . 0.2(8) Y
C141 B14 C15 C16 . . . . 173.7(6) Y
N13 B14 C15 C19 . . . . 177.6(6) Y
C141 B14 C15 C19 . . . . -8.90(11) Y
C19 C15 C16 C11 . . . . 179.3(5) Y
B14 C15 C16 C11 . . . . -2.7(8) Y
C19 C15 C16 S17 . . . . 0.8(6) Y
B14 C15 C16 S17 . . . . 178.7(4) Y
C12 C11 C16 C15 . . . . 3.5(8) Y
S11 C11 C16 C15 . . . . -176.3(4) Y
C12 C11 C16 S17 . . . . -178.2(4) Y
S11 C11 C16 S17 . . . . 2.1(8) Y
C15 C16 S17 C18 . . . . -0.5(5) Y
C11 C16 S17 C18 . . . . -179.0(5) Y
C16 S17 C18 C19 . . . . 0.1(5) Y
S17 C18 C19 C15 . . . . 0.3(7) Y
C16 C15 C19 C18 . . . . -0.7(8) Y
B14 C15 C19 C18 . . . . -178.3(6) Y
N13 B14 C141 C146 . . . . 27.2(8) Y
C15 B14 C141 C146 . . . . -146.2(6) Y
N13 B14 C141 C142 . . . . -156.1(5) Y
C15 B14 C141 C142 . . . . 30.5(9) Y
C146 C141 C142 C143 . . . . -0.2(9) Y
B14 C141 C142 C143 . . . . -177.1(5) Y
C141 C142 C143 C144 . . . . 0.0(1) Y
C142 C143 C144 C145 . . . . -0.3(1) Y
C143 C144 C145 C146 . . . . 1.0(1) Y
C142 C141 C146 C145 . . . . 0.8(9) Y
B14 C141 C146 C145 . . . . 177.7(5) Y
C144 C145 C146 C141 . . . . -1.2(1) Y
C21 S21 C21 C22 2_655 . . . -1.0(3) Y
C21 S21 C21 C26 2_655 . . . -178.2(6) Y
C26 C21 C22 N23 . . . . -0.8(8) Y
S21 C21 C22 N23 . . . . -178.1(4) Y
C26 C21 C22 C22 . . . 2_655 -180.0(5) Y
S21 C21 C22 C22 . . . 2_655 2.7(8) Y
C21 C22 N23 B24 . . . . 3.1(8) Y
C22 C22 N23 B24 2_655 . . . -177.9(6) Y
C22 N23 B24 C25 . . . . -4.1(7) Y
C22 N23 B24 C241 . . . . 175.6(5) Y
N23 B24 C25 C26 . . . . 3.0(7) Y
C241 B24 C25 C26 . . . . -176.6(5) Y
N23 B24 C25 C29 . . . . 178.2(5) Y
C241 B24 C25 C29 . . . . -1.4(1) Y
C29 C25 C26 C21 . . . . -177.3(5) Y
B24 C25 C26 C21 . . . . -1.1(7) Y
C29 C25 C26 S27 . . . . 3.1(6) Y
B24 C25 C26 S27 . . . . 179.4(4) Y
C22 C21 C26 C25 . . . . -0.1(8) Y
S21 C21 C26 C25 . . . . 176.8(4) Y
C22 C21 C26 S27 . . . . 179.4(4) Y
S21 C21 C26 S27 . . . . -3.7(8) Y
C25 C26 S27 C28 . . . . -2.4(4) Y
C21 C26 S27 C28 . . . . 178.0(5) Y
C26 S27 C28 C29 . . . . 1.0(5) Y
S27 C28 C29 C25 . . . . 0.6(7) Y
C26 C25 C29 C28 . . . . -2.4(7) Y
B24 C25 C29 C28 . . . . -177.9(6) Y
N23 B24 C241 C242 . . . . 150.3(5) Y
C25 B24 C241 C242 . . . . -30.1(9) Y
N23 B24 C241 C246 . . . . -36.0(8) Y
C25 B24 C241 C246 . . . . 143.6(6) Y
C246 C241 C242 C243 . . . . 1.1(9) Y
B24 C241 C242 C243 . . . . 175.3(6) Y
C241 C242 C243 C244 . . . . -1.1(1) Y
C242 C243 C244 C245 . . . . 0.9(1) Y
C243 C244 C245 C246 . . . . -0.80(11) Y
C244 C245 C246 C241 . . . . 0.9(1) Y
C242 C241 C246 C245 . . . . -1.0(9) Y
B24 C241 C246 C245 . . . . -175.0(6) Y

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
N13 H13 O41 0.88 2.19 3.057(6) 170.3 .
N23 H23 O31 0.88 2.17 3.041(7) 172 .

_diffrn_measured_fraction_theta_max 0.912
_diffrn_reflns_theta_full        67.17
_diffrn_measured_fraction_theta_full 0.912
_refine_diff_density_max         1.386
_refine_diff_density_min         -0.819
_refine_diff_density_rms         0.154

# start Validation Reply Form
_vrf_PLAT029_perep7              
;
PROBLEM: _diffrn_measured_fraction_theta_full Low ....... 0.91
RESPONSE: All available geometric data up to given 2theta-limit was collected
with an optimized data collection strategy. Missing data is due to geometric
restraints of the instruments.
;
_vrf_PLAT733_perep7              
;
PROBLEM: Torsion Calc -8.9(10), Rep -8.90(11) ...... 9.09 su-Ra
RESPONSE: Su from SHELX were calculated with full matrix, not with PLATON
;
# start Validation Reply Form
_vrf_DIFMX01_PEREP7              
;
PROBLEM: The maximum difference density is > 0.1*ZMAX*0.75
_refine_diff_density_max given = 1.450
RESPONSE: Undefined twinning might be cause errors in the intensities of some
reflections and residual electron density larger than expected.
;
_vrf_PLAT318_PEREP7              
;
PROBLEM: Check Hybridisation of N13 in Main Residue .
RESPONSE: Hydrogen of N13 were calculated as N13 and N43 are sp2 and were
involved in good hydrogen bonds. The angles N-H---O were around 170 degrees.
;
_vrf_ABSTM02_PEREP7              
;
PROBLEM:The ratio of expected to reported Tmax/Tmin(RR') is < 0.75
RESPONSE: Most likely due to small errors in the determination of crystal
dimensions
;
_vrf_PLAT244_PEREP7              
;
PROBLEM: Low 'Solvent' Ueq as Compared to Neighbors for C31, c41
RESPONSE: Error messages related to the observed disorder in acetone.
;

# end Validation Reply Form

# Attachment '- perep8.cif'

data_perep8
_database_code_depnum_ccdc_archive 'CCDC 782156'
#TrackingRef '- perep8.cif'

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_sum            'C26 H18 B2 N2 S3'
_chemical_formula_weight         476.22
_chemical_compound_source        'Synthesized by the authors. See text'

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 '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 0.0090 0.0039 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.3331 0.5567 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           Triclinic
_symmetry_space_group_name_H-M   P-1
_symmetry_space_group_name_hall  '-P 1'

loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   9.1410(3)
_cell_length_b                   10.7737(4)
_cell_length_c                   12.6073(5)
_cell_angle_alpha                105.745(2)
_cell_angle_beta                 107.589(2)
_cell_angle_gamma                92.225(2)
_cell_volume                     1129.22(7)
_cell_formula_units_Z            2
_cell_measurement_temperature    150
_cell_measurement_reflns_used    6245
_cell_measurement_theta_min      3.85
_cell_measurement_theta_max      70.62

_exptl_crystal_description       CHUNK
_exptl_crystal_colour            'YELLOW PALE'
_exptl_crystal_size_max          0.15
_exptl_crystal_size_mid          0.08
_exptl_crystal_size_min          0.03
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.401
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             492
_exptl_absorpt_coefficient_mu    3.133
_exptl_absorpt_correction_Type   multi-scan
_exptl_absorpt_correction_T_min  0.5884
_exptl_absorpt_correction_T_max  0.9103
_exptl_absorpt_process_details   'Sadabs (Sheldrick, 1996)'

_exptl_special_details           
;
X-ray crystallographic data for I were collected from a single crystal
sample, which was mounted on a loop fiber. Data were collected using
a Bruker Platform diffractometer, equipped with a Bruker SMART 4K
Charged-Coupled Device (CCD) Area Detector using the program APEX2 and
a Nonius FR591 rotating anode equiped with a Montel 200 optics
The crystal-to-detector distance was 5.0 cm, and the data collection
was carried out in 512 x 512 pixel mode.
The initial unit cell parameters were determined by a least-squares fit
of the angular setting of strong reflections, collected by a 10.0 degree
scan in 33 frames over four different parts of the reciprocal space
(132 frames total). One complete sphere of data was collected, to
better than 0.80\%A resolution.
;

_diffrn_ambient_temperature      150
_diffrn_radiation_wavelength     1.54178
_diffrn_radiation_type           CuK\a
_diffrn_radiation_source         'Rotating Anode'
_diffrn_radiation_monochromator  'Montel 200 optics'
_diffrn_measurement_device_type  'Bruker Smart 6000'
_diffrn_measurement_method       \w
_diffrn_detector_area_resol_mean 5.5
_diffrn_standards_number         108
_diffrn_standards_interval_time  1380
_diffrn_standards_decay_%        1.10
_diffrn_reflns_number            13485
_diffrn_reflns_av_R_equivalents  0.036
_diffrn_reflns_av_sigmaI/netI    0.0328
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_theta_min         3.85
_diffrn_reflns_theta_max         71.06
_reflns_number_total             4168
_reflns_number_gt                3609
_reflns_threshold_expression     I>2\s(I)

_computing_data_collection       'APEX2 v2.1-0 (Bruker AXS, 2006a)'
_computing_cell_refinement       'SAINT V7.34A (Bruker AXS, 2006b)'
_computing_data_reduction        'SAINT V7.34A (Bruker AXS, 2006b)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 2008)'
_computing_molecular_graphics    'SHELXTL v6.12 (Bruker AXS, 2001)'
_computing_publication_material  'UdMX (Maris, 2004)'

_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^)+(0.0913P)^2^] 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     SHELXL
_refine_ls_extinction_coef       0.0050(6)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_number_reflns         4168
_refine_ls_number_parameters     299
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0419
_refine_ls_R_factor_gt           0.0365
_refine_ls_wR_factor_ref         0.1172
_refine_ls_wR_factor_gt          0.1115
_refine_ls_goodness_of_fit_ref   1.009
_refine_ls_restrained_S_all      1.009
_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
S1 S 0.16148(5) 0.42320(4) -0.12399(4) 0.02658(15) Uani 1 1 d . . .
C11 C 0.29679(19) 0.55642(16) -0.03087(15) 0.0241(4) Uani 1 1 d . . .
C12 C 0.32189(18) 0.56508(16) 0.08483(15) 0.0226(4) Uani 1 1 d . . .
C13 C 0.39307(19) 0.66910(16) 0.28878(14) 0.0240(4) Uani 1 1 d . . .
H13A H 0.2989 0.7089 0.2946 0.029 Uiso 1 1 calc R . .
H13B H 0.4826 0.7235 0.3536 0.029 Uiso 1 1 calc R . .
N13 N 0.41368(15) 0.66861(13) 0.17658(11) 0.0221(3) Uani 1 1 d . . .
B14 B 0.4967(2) 0.76982(19) 0.15668(17) 0.0231(4) Uani 1 1 d . . .
C15 C 0.47913(19) 0.75410(17) 0.02815(15) 0.0241(4) Uani 1 1 d . . .
C16 C 0.3741(2) 0.65312(17) -0.05941(15) 0.0246(4) Uani 1 1 d . . .
S17 S 0.34730(5) 0.66777(4) -0.19694(4) 0.03052(15) Uani 1 1 d . . .
C18 C 0.4797(2) 0.80703(18) -0.14006(16) 0.0336(4) Uani 1 1 d . . .
H18 H 0.5080 0.8543 -0.1860 0.040 Uiso 1 1 calc R . .
C19 C 0.5384(2) 0.84100(18) -0.02235(16) 0.0297(4) Uani 1 1 d . . .
H19 H 0.6122 0.9156 0.0228 0.036 Uiso 1 1 calc R . .
C141 C 0.58496(19) 0.89754(17) 0.25634(14) 0.0245(4) Uani 1 1 d . . .
C142 C 0.7351(2) 0.94626(19) 0.26809(17) 0.0323(4) Uani 1 1 d . . .
H142 H 0.7866 0.8979 0.2185 0.039 Uiso 1 1 calc R . .
C143 C 0.8110(2) 1.0631(2) 0.34999(18) 0.0419(5) Uani 1 1 d . . .
H143 H 0.9129 1.0936 0.3559 0.050 Uiso 1 1 calc R . .
C144 C 0.7381(2) 1.1352(2) 0.42319(17) 0.0405(5) Uani 1 1 d . . .
H144 H 0.7901 1.2150 0.4797 0.049 Uiso 1 1 calc R . .
C145 C 0.5898(2) 1.09061(18) 0.41348(16) 0.0333(4) Uani 1 1 d . . .
H145 H 0.5389 1.1404 0.4627 0.040 Uiso 1 1 calc R . .
C146 C 0.5144(2) 0.97317(16) 0.33208(14) 0.0263(4) Uani 1 1 d . . .
H146 H 0.4129 0.9432 0.3274 0.032 Uiso 1 1 calc R . .
C21 C 0.1416(2) 0.37791(17) -0.00560(15) 0.0247(4) Uani 1 1 d . . .
C22 C 0.23667(19) 0.46162(16) 0.09865(15) 0.0238(4) Uani 1 1 d . . .
C23 C 0.37859(19) 0.53327(16) 0.30171(14) 0.0249(4) Uani 1 1 d . . .
H23A H 0.4760 0.4960 0.3022 0.030 Uiso 1 1 calc R . .
H23B H 0.3632 0.5390 0.3772 0.030 Uiso 1 1 calc R . .
N23 N 0.24796(16) 0.44579(14) 0.20623(12) 0.0238(3) Uani 1 1 d . . .
B24 B 0.1535(2) 0.34232(19) 0.21478(18) 0.0245(4) Uani 1 1 d . . .
C25 C 0.04099(19) 0.25380(16) 0.09925(15) 0.0245(4) Uani 1 1 d . . .
C26 C 0.04307(19) 0.27268(16) -0.00570(15) 0.0246(4) Uani 1 1 d . . .
S27 S -0.08869(5) 0.16136(4) -0.12563(4) 0.02857(15) Uani 1 1 d . . .
C28 C -0.1521(2) 0.09024(17) -0.03749(16) 0.0297(4) Uani 1 1 d . . .
H28 H -0.2326 0.0192 -0.0662 0.036 Uiso 1 1 calc R . .
C29 C -0.0742(2) 0.14709(17) 0.07750(16) 0.0279(4) Uani 1 1 d . . .
H29 H -0.0939 0.1190 0.1377 0.033 Uiso 1 1 calc R . .
C241 C 0.17025(19) 0.32082(17) 0.33664(15) 0.0256(4) Uani 1 1 d . . .
C242 C 0.20300(19) 0.20161(17) 0.35663(16) 0.0291(4) Uani 1 1 d . . .
H242 H 0.2174 0.1336 0.2960 0.035 Uiso 1 1 calc R . .
C243 C 0.2150(2) 0.1802(2) 0.46198(18) 0.0368(5) Uani 1 1 d . . .
H243 H 0.2391 0.0987 0.4732 0.044 Uiso 1 1 calc R . .
C244 C 0.1921(2) 0.2765(2) 0.55102(17) 0.0401(5) Uani 1 1 d . . .
H244 H 0.1994 0.2612 0.6231 0.048 Uiso 1 1 calc R . .
C245 C 0.1586(2) 0.3951(2) 0.53439(17) 0.0402(5) Uani 1 1 d . . .
H245 H 0.1420 0.4616 0.5950 0.048 Uiso 1 1 calc R . .
C246 C 0.1492(2) 0.41704(18) 0.42902(16) 0.0330(4) Uani 1 1 d . . .
H246 H 0.1278 0.4996 0.4193 0.040 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
S1 0.0305(2) 0.0256(2) 0.0201(2) 0.00491(17) 0.00529(18) -0.00074(18)
C11 0.0257(8) 0.0236(9) 0.0222(9) 0.0057(7) 0.0076(7) 0.0026(7)
C12 0.0209(8) 0.0238(8) 0.0226(9) 0.0068(7) 0.0062(7) 0.0029(7)
C13 0.0244(8) 0.0272(9) 0.0197(8) 0.0069(7) 0.0067(7) -0.0004(7)
N13 0.0219(7) 0.0251(7) 0.0175(7) 0.0056(6) 0.0046(6) 0.0003(6)
B14 0.0202(9) 0.0253(9) 0.0239(10) 0.0070(8) 0.0073(7) 0.0029(7)
C15 0.0236(8) 0.0260(9) 0.0242(9) 0.0076(7) 0.0098(7) 0.0044(7)
C16 0.0280(8) 0.0251(9) 0.0218(8) 0.0071(7) 0.0095(7) 0.0042(7)
S17 0.0403(3) 0.0300(3) 0.0214(2) 0.00693(18) 0.0112(2) 0.00140(19)
C18 0.0431(11) 0.0313(10) 0.0300(10) 0.0111(8) 0.0159(8) -0.0002(8)
C19 0.0338(9) 0.0287(9) 0.0278(9) 0.0084(7) 0.0124(8) -0.0004(7)
C141 0.0236(8) 0.0289(9) 0.0213(9) 0.0105(7) 0.0056(7) -0.0003(7)
C142 0.0263(9) 0.0400(11) 0.0287(9) 0.0097(8) 0.0076(7) -0.0031(8)
C143 0.0296(10) 0.0500(12) 0.0389(11) 0.0120(10) 0.0045(9) -0.0149(9)
C144 0.0452(11) 0.0362(11) 0.0272(10) 0.0022(8) 0.0023(8) -0.0146(9)
C145 0.0409(10) 0.0312(10) 0.0239(9) 0.0050(8) 0.0086(8) -0.0003(8)
C146 0.0252(8) 0.0280(9) 0.0241(9) 0.0082(7) 0.0060(7) -0.0008(7)
C21 0.0251(8) 0.0250(9) 0.0220(9) 0.0057(7) 0.0061(7) 0.0019(7)
C22 0.0217(8) 0.0257(9) 0.0225(9) 0.0069(7) 0.0051(7) 0.0023(7)
C23 0.0230(8) 0.0282(9) 0.0201(8) 0.0072(7) 0.0025(7) -0.0021(7)
N23 0.0223(7) 0.0261(7) 0.0201(7) 0.0063(6) 0.0036(6) 0.0002(6)
B24 0.0222(9) 0.0252(10) 0.0270(10) 0.0084(8) 0.0084(8) 0.0038(8)
C25 0.0220(8) 0.0226(8) 0.0282(9) 0.0073(7) 0.0076(7) 0.0033(7)
C26 0.0211(8) 0.0233(8) 0.0258(9) 0.0052(7) 0.0048(7) 0.0008(7)
S27 0.0255(2) 0.0271(2) 0.0260(3) 0.00383(18) 0.00272(18) -0.00227(17)
C28 0.0231(8) 0.0275(9) 0.0353(10) 0.0066(8) 0.0080(7) -0.0015(7)
C29 0.0233(8) 0.0266(9) 0.0321(10) 0.0072(7) 0.0082(7) 0.0017(7)
C241 0.0191(8) 0.0295(9) 0.0262(9) 0.0075(7) 0.0057(7) -0.0020(7)
C242 0.0238(8) 0.0315(9) 0.0306(10) 0.0106(8) 0.0061(7) 0.0008(7)
C243 0.0254(9) 0.0463(11) 0.0410(11) 0.0249(9) 0.0039(8) 0.0027(8)
C244 0.0254(9) 0.0686(14) 0.0265(10) 0.0213(10) 0.0031(8) 0.0013(9)
C245 0.0316(10) 0.0561(13) 0.0265(10) 0.0031(9) 0.0096(8) -0.0009(9)
C246 0.0310(9) 0.0329(10) 0.0327(10) 0.0056(8) 0.0110(8) 0.0013(8)

_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_site_symmetry_1
_geom_bond_site_symmetry_2
_geom_bond_distance
_geom_bond_publ_flag
S1 C11 . . 1.7431(17) Y
S1 C21 . . 1.7469(18) Y
C11 C12 . . 1.383(2) Y
C11 C16 . . 1.419(2) Y
C12 N13 . . 1.388(2) Y
C12 C22 . . 1.414(2) Y
C13 N13 . . 1.4811(19) Y
C13 C23 . . 1.521(2) Y
C13 H13a . . 0.99 ?
C13 H13b . . 0.99 ?
N13 B14 . . 1.424(2) Y
B14 C15 . . 1.540(2) Y
B14 C141 . . 1.577(2) Y
C15 C16 . . 1.397(2) Y
C15 C19 . . 1.438(2) Y
C16 S17 . . 1.7281(17) Y
S17 C18 . . 1.726(2) Y
C18 C19 . . 1.354(3) Y
C18 H18 . . 0.95 ?
C19 H19 . . 0.95 ?
C141 C142 . . 1.400(2) Y
C141 C146 . . 1.408(2) Y
C142 C143 . . 1.387(3) Y
C142 H142 . . 0.95 ?
C143 C144 . . 1.386(3) Y
C143 H143 . . 0.95 ?
C144 C145 . . 1.379(3) Y
C144 H144 . . 0.95 ?
C145 C146 . . 1.389(2) Y
C145 H145 . . 0.95 ?
C146 H146 . . 0.95 ?
C21 C22 . . 1.379(2) Y
C21 C26 . . 1.420(2) Y
C22 N23 . . 1.386(2) Y
C23 N23 . . 1.480(2) Y
C23 H23a . . 0.99 ?
C23 H23b . . 0.99 ?
N23 B24 . . 1.430(2) Y
B24 C25 . . 1.534(2) Y
B24 C241 . . 1.578(2) Y
C25 C26 . . 1.398(2) Y
C25 C29 . . 1.437(2) Y
C26 S27 . . 1.7257(17) Y
S27 C28 . . 1.7247(19) Y
C28 C29 . . 1.358(3) Y
C28 H28 . . 0.95 ?
C29 H29 . . 0.95 ?
C241 C242 . . 1.401(2) Y
C241 C246 . . 1.402(2) Y
C242 C243 . . 1.382(2) Y
C242 H242 . . 0.95 ?
C243 C244 . . 1.381(3) Y
C243 H243 . . 0.95 ?
C244 C245 . . 1.381(3) Y
C244 H244 . . 0.95 ?
C245 C246 . . 1.390(3) Y
C245 H245 . . 0.95 ?
C246 H246 . . 0.95 ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_2
_geom_angle_site_symmetry_3
_geom_angle
_geom_angle_publ_flag
C11 S1 C21 . . . 91.11(8) Y
C12 C11 C16 . . . 119.53(16) Y
C12 C11 S1 . . . 111.63(13) Y
C16 C11 S1 . . . 128.79(14) Y
C11 C12 N13 . . . 123.18(15) Y
C11 C12 C22 . . . 112.63(15) Y
N13 C12 C22 . . . 124.09(15) Y
N13 C13 C23 . . . 112.57(13) Y
N13 C13 H13A . . . 109.1 ?
C23 C13 H13A . . . 109.1 ?
N13 C13 H13B . . . 109.1 ?
C23 C13 H13B . . . 109.1 ?
H13A C13 H13B . . . 107.8 ?
C12 N13 B14 . . . 121.29(14) Y
C12 N13 C13 . . . 111.98(13) Y
B14 N13 C13 . . . 126.06(14) Y
N13 B14 C15 . . . 115.35(15) Y
N13 B14 C141 . . . 122.84(15) Y
C15 B14 C141 . . . 121.44(15) Y
C16 C15 C19 . . . 110.08(15) Y
C16 C15 B14 . . . 119.57(16) Y
C19 C15 B14 . . . 129.61(16) Y
C15 C16 C11 . . . 120.60(16) Y
C15 C16 S17 . . . 112.50(13) Y
C11 C16 S17 . . . 126.83(14) Y
C18 S17 C16 . . . 91.28(9) Y
C19 C18 S17 . . . 112.12(14) Y
C19 C18 H18 . . . 123.9 ?
S17 C18 H18 . . . 123.9 ?
C18 C19 C15 . . . 114.00(17) Y
C18 C19 H19 . . . 123 ?
C15 C19 H19 . . . 123 ?
C142 C141 C146 . . . 116.59(16) Y
C142 C141 B14 . . . 120.91(15) Y
C146 C141 B14 . . . 122.35(15) Y
C143 C142 C141 . . . 121.91(18) Y
C143 C142 H142 . . . 119 ?
C141 C142 H142 . . . 119 ?
C144 C143 C142 . . . 120.06(18) Y
C144 C143 H143 . . . 120 ?
C142 C143 H143 . . . 120 ?
C145 C144 C143 . . . 119.58(18) Y
C145 C144 H144 . . . 120.2 ?
C143 C144 H144 . . . 120.2 ?
C144 C145 C146 . . . 120.32(18) Y
C144 C145 H145 . . . 119.8 ?
C146 C145 H145 . . . 119.8 ?
C145 C146 C141 . . . 121.54(16) Y
C145 C146 H146 . . . 119.2 ?
C141 C146 H146 . . . 119.2 ?
C22 C21 C26 . . . 119.86(16) Y
C22 C21 S1 . . . 111.30(13) Y
C26 C21 S1 . . . 128.84(14) Y
C21 C22 N23 . . . 123.39(16) Y
C21 C22 C12 . . . 113.26(15) Y
N23 C22 C12 . . . 123.35(15) Y
N23 C23 C13 . . . 111.98(13) Y
N23 C23 H23A . . . 109.2 ?
C13 C23 H23A . . . 109.2 ?
N23 C23 H23B . . . 109.2 ?
C13 C23 H23B . . . 109.2 ?
H23A C23 H23B . . . 107.9 ?
C22 N23 B24 . . . 120.68(15) Y
C22 N23 C23 . . . 112.37(14) Y
B24 N23 C23 . . . 126.41(14) Y
N23 B24 C25 . . . 115.90(16) Y
N23 B24 C241 . . . 120.86(16) Y
C25 B24 C241 . . . 123.22(15) Y
C26 C25 C29 . . . 110.36(15) Y
C26 C25 B24 . . . 119.55(15) Y
C29 C25 B24 . . . 130.09(16) Y
C25 C26 C21 . . . 120.43(15) Y
C25 C26 S27 . . . 112.53(12) Y
C21 C26 S27 . . . 126.98(14) Y
C28 S27 C26 . . . 91.17(8) Y
C29 C28 S27 . . . 112.47(14) Y
C29 C28 H28 . . . 123.8 ?
S27 C28 H28 . . . 123.8 ?
C28 C29 C25 . . . 113.44(17) Y
C28 C29 H29 . . . 123.3 ?
C25 C29 H29 . . . 123.3 ?
C242 C241 C246 . . . 116.40(16) Y
C242 C241 B24 . . . 121.08(15) Y
C246 C241 B24 . . . 122.50(16) Y
C243 C242 C241 . . . 121.87(17) Y
C243 C242 H242 . . . 119.1 ?
C241 C242 H242 . . . 119.1 ?
C244 C243 C242 . . . 120.40(18) Y
C244 C243 H243 . . . 119.8 ?
C242 C243 H243 . . . 119.8 ?
C243 C244 C245 . . . 119.44(18) Y
C243 C244 H244 . . . 120.3 ?
C245 C244 H244 . . . 120.3 ?
C244 C245 C246 . . . 120.02(18) Y
C244 C245 H245 . . . 120 ?
C246 C245 H245 . . . 120 ?
C245 C246 C241 . . . 121.85(18) Y
C245 C246 H246 . . . 119.1 ?
C241 C246 H246 . . . 119.1 ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion
_geom_torsion_publ_flag
C21 S1 C11 C12 . . . . -0.91(13) Y
C21 S1 C11 C16 . . . . -178.37(17) Y
C16 C11 C12 N13 . . . . 3.6(3) Y
S1 C11 C12 N13 . . . . -174.09(12) Y
C16 C11 C12 C22 . . . . -179.99(15) Y
S1 C11 C12 C22 . . . . 2.28(18) Y
C11 C12 N13 B14 . . . . -4.1(2) Y
C22 C12 N13 B14 . . . . 179.97(16) Y
C11 C12 N13 C13 . . . . 167.07(15) Y
C22 C12 N13 C13 . . . . -8.9(2) Y
C23 C13 N13 C12 . . . . 39.76(18) Y
C23 C13 N13 B14 . . . . -149.60(16) Y
C12 N13 B14 C15 . . . . -1.0(2) Y
C13 N13 B14 C15 . . . . -170.87(14) Y
C12 N13 B14 C141 . . . . 172.04(14) Y
C13 N13 B14 C141 . . . . 2.2(3) Y
N13 B14 C15 C16 . . . . 6.6(2) Y
C141 B14 C15 C16 . . . . -166.59(15) Y
N13 B14 C15 C19 . . . . 175.74(17) Y
C141 B14 C15 C19 . . . . 2.6(3) Y
C19 C15 C16 C11 . . . . -178.41(16) Y
B14 C15 C16 C11 . . . . -7.3(2) Y
C19 C15 C16 S17 . . . . -1.32(18) Y
B14 C15 C16 S17 . . . . 169.80(12) Y
C12 C11 C16 C15 . . . . 2.3(2) Y
S1 C11 C16 C15 . . . . 179.57(13) Y
C12 C11 C16 S17 . . . . -174.35(13) Y
S1 C11 C16 S17 . . . . 2.9(2) Y
C15 C16 S17 C18 . . . . 1.36(14) Y
C11 C16 S17 C18 . . . . 178.23(16) Y
C16 S17 C18 C19 . . . . -1.03(15) Y
S17 C18 C19 C15 . . . . 0.5(2) Y
C16 C15 C19 C18 . . . . 0.5(2) Y
B14 C15 C19 C18 . . . . -169.42(17) Y
N13 B14 C141 C142 . . . . 134.67(18) Y
C15 B14 C141 C142 . . . . -52.7(2) Y
N13 B14 C141 C146 . . . . -50.0(2) Y
C15 B14 C141 C146 . . . . 122.63(18) Y
C146 C141 C142 C143 . . . . 0.0(3) Y
B14 C141 C142 C143 . . . . 175.54(18) Y
C141 C142 C143 C144 . . . . 0.0(3) Y
C142 C143 C144 C145 . . . . -0.4(3) Y
C143 C144 C145 C146 . . . . 0.9(3) Y
C144 C145 C146 C141 . . . . -1.0(3) Y
C142 C141 C146 C145 . . . . 0.5(3) Y
B14 C141 C146 C145 . . . . -174.95(16) Y
C11 S1 C21 C22 . . . . -0.71(13) Y
C11 S1 C21 C26 . . . . 178.32(17) Y
C26 C21 C22 N23 . . . . 3.2(3) Y
S1 C21 C22 N23 . . . . -177.70(13) Y
C26 C21 C22 C12 . . . . -176.99(15) Y
S1 C21 C22 C12 . . . . 2.14(19) Y
C11 C12 C22 C21 . . . . -2.9(2) Y
N13 C12 C22 C21 . . . . 173.45(15) Y
C11 C12 C22 N23 . . . . 176.97(15) Y
N13 C12 C22 N23 . . . . -6.7(3) Y
N13 C13 C23 N23 . . . . -57.86(18) Y
C21 C22 N23 B24 . . . . -3.0(3) Y
C12 C22 N23 B24 . . . . 177.21(15) Y
C21 C22 N23 C23 . . . . 169.10(15) Y
C12 C22 N23 C23 . . . . -10.7(2) Y
C13 C23 N23 C22 . . . . 41.33(19) Y
C13 C23 N23 B24 . . . . -147.16(16) Y
C22 N23 B24 C25 . . . . -0.6(2) Y
C23 N23 B24 C25 . . . . -171.49(14) Y
C22 N23 B24 C241 . . . . 177.76(14) Y
C23 N23 B24 C241 . . . . 6.9(3) Y
N23 B24 C25 C26 . . . . 4.0(2) Y
C241 B24 C25 C26 . . . . -174.36(15) Y
N23 B24 C25 C29 . . . . -176.25(16) Y
C241 B24 C25 C29 . . . . 5.4(3) Y
C29 C25 C26 C21 . . . . 176.26(15) Y
B24 C25 C26 C21 . . . . -3.9(2) Y
C29 C25 C26 S27 . . . . -1.18(18) Y
B24 C25 C26 S27 . . . . 178.63(12) Y
C22 C21 C26 C25 . . . . 0.5(3) Y
S1 C21 C26 C25 . . . . -178.51(13) Y
C22 C21 C26 S27 . . . . 177.49(13) Y
S1 C21 C26 S27 . . . . -1.5(2) Y
C25 C26 S27 C28 . . . . 1.38(13) Y
C21 C26 S27 C28 . . . . -175.85(16) Y
C26 S27 C28 C29 . . . . -1.23(14) Y
S27 C28 C29 C25 . . . . 0.8(2) Y
C26 C25 C29 C28 . . . . 0.3(2) Y
B24 C25 C29 C28 . . . . -179.52(16) Y
N23 B24 C241 C242 . . . . -123.34(18) Y
C25 B24 C241 C242 . . . . 54.9(2) Y
N23 B24 C241 C246 . . . . 58.5(2) Y
C25 B24 C241 C246 . . . . -123.22(19) Y
C246 C241 C242 C243 . . . . -0.4(2) Y
B24 C241 C242 C243 . . . . -178.68(16) Y
C241 C242 C243 C244 . . . . 1.1(3) Y
C242 C243 C244 C245 . . . . -0.6(3) Y
C243 C244 C245 C246 . . . . -0.4(3) Y
C244 C245 C246 C241 . . . . 1.1(3) Y
C242 C241 C246 C245 . . . . -0.6(3) Y
B24 C241 C246 C245 . . . . 177.57(17) Y

_diffrn_measured_fraction_theta_max 0.952
_diffrn_reflns_theta_full        71.06
_diffrn_measured_fraction_theta_full 0.952
_refine_diff_density_max         0.268
_refine_diff_density_min         -0.327
_refine_diff_density_rms         0.076