# Supplementary Material (ESI) for Chemical Communications
# This journal is © The Royal Society of Chemistry 2005



data_global
_journal_name_full               Chem.Commun.

_journal_coden_Cambridge         0182

_publ_contact_author_name        'Yoshihiko Yamamoto'
_publ_contact_author_address     
;
Department of Applied Chemistry
Graduate School of Engineering
Chikusa
Nagoya
464-8603
JAPAN
;

_publ_contact_author_email       YAMAMOTO@APCHEM.NAGOYA-U.AC.JP

_publ_section_title              
;
Synthesis of bi- and tricyclic arylboronates via
Cp*RuCl-catalyzed cycloaddition of ?,?-diynes with ethynylboronate
;
loop_
_publ_author_name
'Yoshihiko Yamamoto'
'Kozo Hattori'
'Jun-ichi Ishii'
'Keiji Itoh'
'Hisao Nishiyama'

data_yh1
_database_code_depnum_ccdc_archive 'CCDC 271948'

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C18 H23 B O6'
_chemical_formula_weight         346.17

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'

_symmetry_cell_setting           Triclinic
_symmetry_space_group_name_H-M   P-1

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

_cell_length_a                   6.0252(4)
_cell_length_b                   12.4955(9)
_cell_length_c                   13.2849(9)
_cell_angle_alpha                62.7990(10)
_cell_angle_beta                 84.221(2)
_cell_angle_gamma                84.2950(10)
_cell_volume                     883.45(11)
_cell_formula_units_Z            2
_cell_measurement_temperature    173(2)
_cell_measurement_reflns_used    ?
_cell_measurement_theta_min      ?
_cell_measurement_theta_max      ?

_exptl_crystal_description       plate
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.05
_exptl_crystal_size_mid          0.6
_exptl_crystal_size_min          0.8
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.301
_exptl_crystal_density_method    ?
_exptl_crystal_F_000             368
_exptl_absorpt_coefficient_mu    0.096
_exptl_absorpt_correction_type   'empirical (SADABS)'
_exptl_absorpt_correction_T_min  0.115529
_exptl_absorpt_correction_T_max  1.000000
_exptl_absorpt_process_details   ?

_exptl_special_details           
;
?
;

_diffrn_ambient_temperature      173(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            6887
_diffrn_reflns_av_R_equivalents  0.0307
_diffrn_reflns_av_sigmaI/netI    0.0297
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_theta_min         1.73
_diffrn_reflns_theta_max         29.13
_reflns_number_total             4645
_reflns_number_gt                3876
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Bruker SMART'
_computing_cell_refinement       'Bruker SMART'
_computing_data_reduction        'Bruker SHELXTL'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_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^)+(0.2000P)^2^+0.0000P] 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    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         4645
_refine_ls_number_parameters     230
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0790
_refine_ls_R_factor_gt           0.0726
_refine_ls_wR_factor_ref         0.2337
_refine_ls_wR_factor_gt          0.2234
_refine_ls_goodness_of_fit_ref   0.991
_refine_ls_restrained_S_all      0.991
_refine_ls_shift/su_max          0.123
_refine_ls_shift/su_mean         0.022

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
B1 B 0.0531(3) 0.58373(14) 1.09145(13) 0.0269(3) Uani 1 1 d . . .
C1 C -0.3206(2) 0.88187(12) 0.97679(11) 0.0253(3) Uani 1 1 d . . .
H1 H -0.4679 0.9077 0.9861 0.030 Uiso 1 1 calc R . .
C2 C -0.1690(2) 0.96324(12) 0.90170(10) 0.0233(3) Uani 1 1 d . . .
C3 C -0.2027(2) 1.09744(11) 0.82916(10) 0.0240(3) Uani 1 1 d . . .
H3A H -0.1948 1.1412 0.8729 0.029 Uiso 1 1 calc R . .
H3B H -0.3450 1.1184 0.7945 0.029 Uiso 1 1 calc R . .
C4 C -0.0046(2) 1.12327(11) 0.73901(11) 0.0227(3) Uani 1 1 d . . .
C5 C 0.1821(2) 1.02831(12) 0.80208(11) 0.0257(3) Uani 1 1 d . . .
H5A H 0.2783 1.0061 0.7506 0.031 Uiso 1 1 calc R . .
H5B H 0.2722 1.0576 0.8398 0.031 Uiso 1 1 calc R . .
C6 C 0.0510(2) 0.92369(12) 0.88674(11) 0.0234(3) Uani 1 1 d . . .
C7 C 0.1220(2) 0.80326(12) 0.94753(11) 0.0253(3) Uani 1 1 d . . .
H7 H 0.2689 0.7777 0.9370 0.030 Uiso 1 1 calc R . .
C8 C -0.0280(2) 0.71998(12) 1.02504(11) 0.0256(3) Uani 1 1 d . . .
C9 C -0.2486(2) 0.76110(12) 1.03792(11) 0.0266(3) Uani 1 1 d . . .
H9 H -0.3495 0.7067 1.0884 0.032 Uiso 1 1 calc R . .
C10 C -0.0606(2) 1.10598(12) 0.63719(11) 0.0256(3) Uani 1 1 d . . .
C11 C -0.3427(3) 1.11327(17) 0.52397(13) 0.0392(4) Uani 1 1 d . . .
H11A H -0.2928 1.1819 0.4567 0.059 Uiso 1 1 calc R . .
H11B H -0.5026 1.1131 0.5273 0.059 Uiso 1 1 calc R . .
H11C H -0.2773 1.0407 0.5224 0.059 Uiso 1 1 calc R . .
C12 C 0.0559(2) 1.25460(12) 0.68917(12) 0.0275(3) Uani 1 1 d . . .
C13 C 0.3428(3) 1.38797(16) 0.62648(18) 0.0490(5) Uani 1 1 d . . .
H13A H 0.2848 1.4348 0.5531 0.074 Uiso 1 1 calc R . .
H13B H 0.5031 1.3868 0.6194 0.074 Uiso 1 1 calc R . .
H13C H 0.2870 1.4233 0.6755 0.074 Uiso 1 1 calc R . .
C14 C -0.0276(3) 0.37757(13) 1.21850(13) 0.0335(3) Uani 1 1 d . . .
H14A H -0.0620 0.3393 1.1732 0.040 Uiso 1 1 calc R . .
H14B H -0.1122 0.3402 1.2909 0.040 Uiso 1 1 calc R . .
C15 C 0.2213(3) 0.35541(13) 1.23848(12) 0.0293(3) Uani 1 1 d . . .
C16 C 0.3467(3) 0.42747(13) 1.12538(13) 0.0332(3) Uani 1 1 d . . .
H16A H 0.5047 0.4216 1.1370 0.040 Uiso 1 1 calc R . .
H16B H 0.3289 0.3928 1.0748 0.040 Uiso 1 1 calc R . .
C17 C 0.2847(3) 0.22106(14) 1.27771(14) 0.0384(4) Uani 1 1 d . . .
H17A H 0.2461 0.1983 1.2220 0.058 Uiso 1 1 calc R . .
H17B H 0.2050 0.1746 1.3488 0.058 Uiso 1 1 calc R . .
H17C H 0.4425 0.2061 1.2869 0.058 Uiso 1 1 calc R . .
C18 C 0.2744(4) 0.39393(16) 1.32685(15) 0.0447(4) Uani 1 1 d . . .
H18A H 0.4329 0.3849 1.3344 0.067 Uiso 1 1 calc R . .
H18B H 0.1999 0.3443 1.3985 0.067 Uiso 1 1 calc R . .
H18C H 0.2239 0.4768 1.3031 0.067 Uiso 1 1 calc R . .
O1 O -0.09689(17) 0.50344(9) 1.16203(9) 0.0329(3) Uani 1 1 d . . .
O2 O 0.26910(18) 0.55234(9) 1.07302(9) 0.0354(3) Uani 1 1 d . . .
O3 O 0.0780(2) 1.08721(17) 0.57511(13) 0.0601(5) Uani 1 1 d . . .
O4 O -0.27571(19) 1.11937(12) 0.62261(9) 0.0388(3) Uani 1 1 d . . .
O5 O -0.0806(2) 1.33713(11) 0.66569(16) 0.0629(5) Uani 1 1 d . . .
O6 O 0.27272(19) 1.26603(10) 0.67393(11) 0.0409(3) 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
B1 0.0276(8) 0.0281(7) 0.0219(7) -0.0091(6) -0.0011(6) 0.0006(5)
C1 0.0233(6) 0.0305(7) 0.0209(6) -0.0118(5) 0.0036(5) 0.0004(5)
C2 0.0239(6) 0.0283(6) 0.0185(6) -0.0121(5) 0.0005(5) 0.0007(5)
C3 0.0238(6) 0.0269(6) 0.0197(6) -0.0104(5) 0.0028(5) 0.0007(5)
C4 0.0213(6) 0.0251(6) 0.0207(6) -0.0102(5) 0.0016(4) -0.0010(4)
C5 0.0198(6) 0.0272(6) 0.0253(6) -0.0083(5) 0.0004(5) -0.0007(4)
C6 0.0226(6) 0.0272(6) 0.0192(6) -0.0096(5) -0.0010(4) -0.0010(5)
C7 0.0222(6) 0.0282(6) 0.0241(6) -0.0113(5) -0.0013(5) 0.0015(5)
C8 0.0266(7) 0.0285(6) 0.0208(6) -0.0108(5) -0.0012(5) -0.0002(5)
C9 0.0267(7) 0.0292(7) 0.0206(6) -0.0090(5) 0.0030(5) -0.0033(5)
C10 0.0247(6) 0.0292(6) 0.0210(6) -0.0104(5) 0.0029(5) -0.0023(5)
C11 0.0377(8) 0.0539(10) 0.0286(7) -0.0204(7) -0.0092(6) 0.0013(7)
C12 0.0259(7) 0.0281(7) 0.0274(7) -0.0120(5) 0.0015(5) -0.0023(5)
C13 0.0406(9) 0.0338(8) 0.0606(11) -0.0102(8) 0.0063(8) -0.0158(7)
C14 0.0329(8) 0.0266(7) 0.0321(7) -0.0066(6) 0.0033(6) -0.0023(5)
C15 0.0351(8) 0.0272(6) 0.0225(6) -0.0094(5) -0.0019(5) 0.0029(5)
C16 0.0314(7) 0.0292(7) 0.0322(7) -0.0100(6) 0.0022(6) 0.0037(5)
C17 0.0503(10) 0.0283(7) 0.0312(8) -0.0102(6) -0.0027(7) 0.0062(6)
C18 0.0617(12) 0.0418(9) 0.0353(8) -0.0217(7) -0.0162(8) 0.0121(8)
O1 0.0263(5) 0.0273(5) 0.0355(6) -0.0067(4) 0.0017(4) -0.0007(4)
O2 0.0303(6) 0.0276(5) 0.0347(6) -0.0047(4) 0.0070(4) 0.0014(4)
O3 0.0299(6) 0.1224(14) 0.0574(8) -0.0680(10) 0.0045(6) -0.0014(7)
O4 0.0271(6) 0.0650(8) 0.0331(6) -0.0308(6) -0.0073(4) 0.0087(5)
O5 0.0325(7) 0.0290(6) 0.1128(13) -0.0211(7) 0.0010(7) -0.0002(5)
O6 0.0285(6) 0.0288(6) 0.0538(7) -0.0095(5) 0.0071(5) -0.0073(4)

_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
B1 O2 1.3527(19) . ?
B1 O1 1.3609(19) . ?
B1 C8 1.570(2) . ?
C1 C2 1.3915(19) . ?
C1 C9 1.3946(18) . ?
C2 C6 1.3959(18) . ?
C2 C3 1.5088(17) . ?
C3 C4 1.5486(17) . ?
C4 C12 1.5302(18) . ?
C4 C10 1.5374(18) . ?
C4 C5 1.5464(17) . ?
C5 C6 1.5100(18) . ?
C6 C7 1.3893(17) . ?
C7 C8 1.407(2) . ?
C8 C9 1.3998(19) . ?
C10 O3 1.1966(18) . ?
C10 O4 1.3128(18) . ?
C11 O4 1.4457(17) . ?
C12 O5 1.1943(18) . ?
C12 O6 1.3137(18) . ?
C13 O6 1.4470(19) . ?
C14 O1 1.4370(17) . ?
C14 C15 1.525(2) . ?
C15 C16 1.520(2) . ?
C15 C18 1.528(2) . ?
C15 C17 1.5325(19) . ?
C16 O2 1.4371(17) . ?

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
O2 B1 O1 123.55(13) . . ?
O2 B1 C8 117.62(13) . . ?
O1 B1 C8 118.81(13) . . ?
C2 C1 C9 119.15(12) . . ?
C1 C2 C6 120.20(12) . . ?
C1 C2 C3 129.38(12) . . ?
C6 C2 C3 110.41(11) . . ?
C2 C3 C4 102.21(10) . . ?
C12 C4 C10 105.31(10) . . ?
C12 C4 C3 110.88(10) . . ?
C10 C4 C3 112.43(10) . . ?
C12 C4 C5 115.21(11) . . ?
C10 C4 C5 108.94(10) . . ?
C3 C4 C5 104.27(10) . . ?
C6 C5 C4 102.41(10) . . ?
C7 C6 C2 120.51(12) . . ?
C7 C6 C5 129.28(12) . . ?
C2 C6 C5 110.19(11) . . ?
C6 C7 C8 120.09(12) . . ?
C9 C8 C7 118.56(12) . . ?
C9 C8 B1 121.84(13) . . ?
C7 C8 B1 119.57(12) . . ?
C1 C9 C8 121.48(13) . . ?
O3 C10 O4 123.58(13) . . ?
O3 C10 C4 123.50(13) . . ?
O4 C10 C4 112.85(11) . . ?
O5 C12 O6 124.21(14) . . ?
O5 C12 C4 123.16(14) . . ?
O6 C12 C4 112.63(11) . . ?
O1 C14 C15 112.91(12) . . ?
C16 C15 C14 107.35(12) . . ?
C16 C15 C18 110.95(14) . . ?
C14 C15 C18 110.52(13) . . ?
C16 C15 C17 108.75(12) . . ?
C14 C15 C17 108.30(13) . . ?
C18 C15 C17 110.85(12) . . ?
O2 C16 C15 112.39(12) . . ?
B1 O1 C14 119.29(12) . . ?
B1 O2 C16 119.59(12) . . ?
C10 O4 C11 116.71(12) . . ?
C12 O6 C13 115.80(13) . . ?

_diffrn_measured_fraction_theta_max 0.975
_diffrn_reflns_theta_full        29.13
_diffrn_measured_fraction_theta_full 0.975
_refine_diff_density_max         0.695
_refine_diff_density_min         -0.421
_refine_diff_density_rms         0.089