# Supplementary Material (ESI) for Chemical Communications
# This journal is (c) The Royal Society of Chemistry 2007

data_global
_journal_name_full               Chem.Commun.

_journal_coden_Cambridge         0182

_publ_contact_author_name        'Rai-Shung Liu'
_publ_contact_author_address     
;
Chemistry
National Tsing Hua university
101, Section 2
Kuang Fu Road
Hsinchu
30013
TAIWAN
;

_publ_contact_author_email       RSLIU@MX.NTHU.EDU.TW

_publ_section_title              
;
Gold-catalyzed Cycloisomerization of
1,6-Diyne-4-en-3-ols to form Naphthyl Ketone Derivatives.
;
loop_
_publ_author_name
'Rai-Shung Liu'
'Jian-Jou Lian'

data_06mr53m
_database_code_depnum_ccdc_archive 'CCDC 630914'

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C23 H16 O'
_chemical_formula_weight         308.36

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'
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                   9.3540(17)
_cell_length_b                   9.4771(18)
_cell_length_c                   10.2788(19)
_cell_angle_alpha                92.763(3)
_cell_angle_beta                 116.301(3)
_cell_angle_gamma                91.150(3)
_cell_volume                     815.1(3)
_cell_formula_units_Z            2
_cell_measurement_temperature    294(2)
_cell_measurement_reflns_used    1994
_cell_measurement_theta_min      2.5
_cell_measurement_theta_max      25

_exptl_crystal_description       lump
_exptl_crystal_colour            yellow
_exptl_crystal_size_max          0.98
_exptl_crystal_size_mid          0.8
_exptl_crystal_size_min          0.09
_exptl_crystal_density_meas      'not measured'
_exptl_crystal_density_diffrn    1.256
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             324
_exptl_absorpt_coefficient_mu    0.075
_exptl_absorpt_correction_type   Empirical
_exptl_absorpt_correction_T_min  0.83150
_exptl_absorpt_correction_T_max  0.94704
_exptl_absorpt_process_details   ?

_exptl_special_details           
;
?
;

_diffrn_ambient_temperature      273(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            9686
_diffrn_reflns_av_R_equivalents  0.0395
_diffrn_reflns_av_sigmaI/netI    0.0479
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_theta_min         2.15
_diffrn_reflns_theta_max         28.34
_reflns_number_total             4060
_reflns_number_gt                2255
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Bruker SMART'
_computing_cell_refinement       'Bruker SMART'
_computing_data_reduction        'Bruker SAINT'
_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^)+(0.0592P)^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    contr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         4060
_refine_ls_number_parameters     217
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0930
_refine_ls_R_factor_gt           0.0490
_refine_ls_wR_factor_ref         0.1294
_refine_ls_wR_factor_gt          0.1121
_refine_ls_goodness_of_fit_ref   0.914
_refine_ls_restrained_S_all      0.914
_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
O1 O 0.06471(12) 0.90339(12) 0.30666(12) 0.0686(3) Uani 1 1 d . . .
C1 C 0.13914(16) 0.80307(16) 0.29597(15) 0.0509(4) Uani 1 1 d . . .
C2 C 0.19681(16) 0.79995(14) 0.18008(15) 0.0495(4) Uani 1 1 d . . .
C3 C 0.36172(16) 0.83331(15) 0.22268(16) 0.0509(4) Uani 1 1 d . . .
C4 C 0.47457(17) 0.85986(16) 0.37010(17) 0.0586(4) Uani 1 1 d . . .
C5 C 0.63145(18) 0.89417(17) 0.40668(19) 0.0663(5) Uani 1 1 d . . .
C6 C 0.68371(19) 0.90139(17) 0.2982(2) 0.0709(5) Uani 1 1 d . . .
C7 C 0.5786(2) 0.87591(17) 0.1562(2) 0.0673(5) Uani 1 1 d . . .
C8 C 0.41570(18) 0.84368(15) 0.11434(18) 0.0569(4) Uani 1 1 d . . .
C9 C 0.3016(2) 0.82464(16) -0.03394(18) 0.0639(4) Uani 1 1 d . . .
C10 C 0.1461(2) 0.79484(17) -0.07098(17) 0.0630(4) Uani 1 1 d . . .
C11 C 0.08964(17) 0.77959(15) 0.03503(16) 0.0520(4) Uani 1 1 d . . .
C12 C -0.08200(17) 0.73816(16) -0.01660(15) 0.0532(4) Uani 1 1 d . . .
C13 C -0.19875(19) 0.81137(17) -0.12560(17) 0.0661(5) Uani 1 1 d . . .
C14 C -0.3577(2) 0.7658(2) -0.18047(18) 0.0798(6) Uani 1 1 d . . .
C15 C -0.4015(2) 0.6493(2) -0.1301(2) 0.0802(6) Uani 1 1 d . . .
C16 C -0.2875(2) 0.57799(18) -0.0220(2) 0.0738(5) Uani 1 1 d . . .
C17 C -0.12861(17) 0.62171(17) 0.03474(17) 0.0611(4) Uani 1 1 d . . .
C18 C 0.17714(16) 0.68716(16) 0.39633(15) 0.0505(4) Uani 1 1 d . . .
C19 C 0.24763(18) 0.56655(18) 0.37515(17) 0.0619(4) Uani 1 1 d . . .
C20 C 0.2809(2) 0.45985(18) 0.4689(2) 0.0715(5) Uani 1 1 d . . .
C21 C 0.2441(2) 0.4711(2) 0.58389(19) 0.0731(5) Uani 1 1 d . . .
C22 C 0.1743(2) 0.5904(2) 0.60620(17) 0.0706(5) Uani 1 1 d . . .
C23 C 0.14140(17) 0.69872(17) 0.51426(17) 0.0596(4) Uani 1 1 d . . .
H4A H 0.4322 0.8615 0.4518 0.080 Uiso 1 1 d . . .
H9A H 0.3431 0.8336 -0.1126 0.080 Uiso 1 1 d . . .
H19A H 0.2711 0.5614 0.2913 0.080 Uiso 1 1 d . . .
H17A H -0.0425 0.5724 0.1200 0.080 Uiso 1 1 d . . .
H6A H 0.7992 0.9251 0.3254 0.080 Uiso 1 1 d . . .
H5A H 0.7109 0.9090 0.5171 0.080 Uiso 1 1 d . . .
H23A H 0.0863 0.7941 0.5170 0.080 Uiso 1 1 d . . .
H10A H 0.0701 0.7804 -0.1783 0.080 Uiso 1 1 d . . .
H21A H 0.2758 0.3932 0.6574 0.080 Uiso 1 1 d . . .
H22A H 0.1487 0.5920 0.6897 0.080 Uiso 1 1 d . . .
H7A H 0.6141 0.8814 0.0789 0.080 Uiso 1 1 d . . .
H13A H -0.1700 0.9071 -0.1672 0.080 Uiso 1 1 d . . .
H16A H -0.3176 0.4836 0.0079 0.080 Uiso 1 1 d . . .
H14A H -0.4372 0.8176 -0.2615 0.080 Uiso 1 1 d . . .
H15A H -0.5183 0.6043 -0.1758 0.080 Uiso 1 1 d . . .
H20A H 0.3197 0.3662 0.4480 0.080 Uiso 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
O1 0.0650(7) 0.0732(8) 0.0758(8) 0.0057(6) 0.0380(6) 0.0180(6)
C1 0.0394(7) 0.0574(9) 0.0535(9) -0.0020(7) 0.0190(7) 0.0015(7)
C2 0.0504(8) 0.0477(8) 0.0538(9) 0.0041(7) 0.0261(7) 0.0052(6)
C3 0.0524(9) 0.0449(8) 0.0595(9) 0.0020(7) 0.0285(8) 0.0034(7)
C4 0.0503(9) 0.0605(10) 0.0641(10) -0.0024(8) 0.0251(8) 0.0020(7)
C5 0.0509(9) 0.0636(11) 0.0795(12) -0.0028(9) 0.0252(9) 0.0016(8)
C6 0.0535(10) 0.0621(11) 0.1038(15) 0.0000(10) 0.0415(11) -0.0010(8)
C7 0.0708(11) 0.0571(10) 0.0912(13) 0.0019(9) 0.0523(11) -0.0011(8)
C8 0.0637(10) 0.0457(9) 0.0709(11) 0.0021(7) 0.0387(9) 0.0004(7)
C9 0.0807(12) 0.0589(10) 0.0661(11) 0.0051(8) 0.0453(10) 0.0005(9)
C10 0.0724(11) 0.0635(10) 0.0541(10) 0.0033(8) 0.0290(9) 0.0028(8)
C11 0.0573(9) 0.0458(8) 0.0530(9) 0.0038(7) 0.0245(8) 0.0051(7)
C12 0.0550(9) 0.0511(9) 0.0493(8) -0.0035(7) 0.0199(7) 0.0049(7)
C13 0.0685(11) 0.0658(11) 0.0544(9) 0.0025(8) 0.0182(9) 0.0153(9)
C14 0.0618(11) 0.0990(15) 0.0585(11) -0.0044(10) 0.0087(9) 0.0248(11)
C15 0.0552(11) 0.0882(14) 0.0806(13) -0.0242(11) 0.0184(10) -0.0024(10)
C16 0.0613(11) 0.0658(11) 0.0870(13) -0.0108(10) 0.0283(10) -0.0046(9)
C17 0.0531(9) 0.0596(10) 0.0637(10) -0.0001(8) 0.0202(8) 0.0004(8)
C18 0.0423(8) 0.0598(10) 0.0472(8) -0.0002(7) 0.0186(7) -0.0031(7)
C19 0.0634(10) 0.0684(11) 0.0580(10) 0.0090(8) 0.0300(8) 0.0093(8)
C20 0.0790(12) 0.0658(11) 0.0686(11) 0.0111(9) 0.0308(10) 0.0120(9)
C21 0.0759(12) 0.0746(12) 0.0572(10) 0.0108(9) 0.0187(9) -0.0031(10)
C22 0.0742(11) 0.0861(13) 0.0512(10) 0.0022(9) 0.0285(9) -0.0099(10)
C23 0.0551(9) 0.0679(11) 0.0540(9) -0.0027(8) 0.0237(8) -0.0057(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_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O1 C1 1.2187(16) . ?
C1 C18 1.482(2) . ?
C1 C2 1.509(2) . ?
C2 C11 1.3803(19) . ?
C2 C3 1.4281(19) . ?
C3 C4 1.4174(19) . ?
C3 C8 1.418(2) . ?
C4 C5 1.371(2) . ?
C4 H4A 1.0753 . ?
C5 C6 1.406(2) . ?
C5 H5A 1.0456 . ?
C6 C7 1.356(2) . ?
C6 H6A 1.0062 . ?
C7 C8 1.410(2) . ?
C7 H7A 0.9910 . ?
C8 C9 1.421(2) . ?
C9 C10 1.350(2) . ?
C9 H9A 1.0461 . ?
C10 C11 1.418(2) . ?
C10 H10A 1.0138 . ?
C11 C12 1.488(2) . ?
C12 C17 1.388(2) . ?
C12 C13 1.397(2) . ?
C13 C14 1.387(2) . ?
C13 H13A 1.0990 . ?
C14 C15 1.371(3) . ?
C14 H14A 0.9963 . ?
C15 C16 1.371(2) . ?
C15 H15A 1.0501 . ?
C16 C17 1.380(2) . ?
C16 H16A 1.0329 . ?
C17 H17A 1.0316 . ?
C18 C19 1.387(2) . ?
C18 C23 1.393(2) . ?
C19 C20 1.374(2) . ?
C19 H19A 0.9785 . ?
C20 C21 1.370(2) . ?
C20 H20A 1.0145 . ?
C21 C22 1.376(2) . ?
C21 H21A 1.0336 . ?
C22 C23 1.375(2) . ?
C22 H22A 0.9878 . ?
C23 H23A 1.0548 . ?

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 C1 C18 121.40(14) . . ?
O1 C1 C2 118.74(14) . . ?
C18 C1 C2 119.84(13) . . ?
C11 C2 C3 120.74(14) . . ?
C11 C2 C1 120.47(13) . . ?
C3 C2 C1 118.46(13) . . ?
C4 C3 C8 118.08(13) . . ?
C4 C3 C2 122.51(14) . . ?
C8 C3 C2 119.40(13) . . ?
C5 C4 C3 120.85(15) . . ?
C5 C4 H4A 120.7 . . ?
C3 C4 H4A 118.3 . . ?
C4 C5 C6 120.38(15) . . ?
C4 C5 H5A 117.9 . . ?
C6 C5 H5A 121.6 . . ?
C7 C6 C5 120.10(14) . . ?
C7 C6 H6A 119.6 . . ?
C5 C6 H6A 120.3 . . ?
C6 C7 C8 121.09(16) . . ?
C6 C7 H7A 120.7 . . ?
C8 C7 H7A 118.2 . . ?
C7 C8 C3 119.47(15) . . ?
C7 C8 C9 122.16(15) . . ?
C3 C8 C9 118.35(14) . . ?
C10 C9 C8 120.91(15) . . ?
C10 C9 H9A 121.6 . . ?
C8 C9 H9A 117.5 . . ?
C9 C10 C11 121.95(14) . . ?
C9 C10 H10A 117.7 . . ?
C11 C10 H10A 120.3 . . ?
C2 C11 C10 118.61(14) . . ?
C2 C11 C12 123.48(14) . . ?
C10 C11 C12 117.88(13) . . ?
C17 C12 C13 118.91(14) . . ?
C17 C12 C11 121.17(13) . . ?
C13 C12 C11 119.78(15) . . ?
C14 C13 C12 119.44(17) . . ?
C14 C13 H13A 118.2 . . ?
C12 C13 H13A 122.3 . . ?
C15 C14 C13 120.91(16) . . ?
C15 C14 H14A 121.7 . . ?
C13 C14 H14A 117.3 . . ?
C14 C15 C16 119.84(16) . . ?
C14 C15 H15A 123.7 . . ?
C16 C15 H15A 116.3 . . ?
C15 C16 C17 120.28(17) . . ?
C15 C16 H16A 120.2 . . ?
C17 C16 H16A 119.0 . . ?
C16 C17 C12 120.61(15) . . ?
C16 C17 H17A 120.9 . . ?
C12 C17 H17A 118.4 . . ?
C19 C18 C23 119.02(15) . . ?
C19 C18 C1 121.26(14) . . ?
C23 C18 C1 119.72(14) . . ?
C20 C19 C18 120.35(16) . . ?
C20 C19 H19A 122.5 . . ?
C18 C19 H19A 117.1 . . ?
C21 C20 C19 120.40(16) . . ?
C21 C20 H20A 118.0 . . ?
C19 C20 H20A 121.2 . . ?
C20 C21 C22 119.79(17) . . ?
C20 C21 H21A 119.8 . . ?
C22 C21 H21A 120.3 . . ?
C23 C22 C21 120.63(16) . . ?
C23 C22 H22A 123.1 . . ?
C21 C22 H22A 116.3 . . ?
C22 C23 C18 119.81(16) . . ?
C22 C23 H23A 128.6 . . ?
C18 C23 H23A 111.6 . . ?

_diffrn_measured_fraction_theta_max 0.994
_diffrn_reflns_theta_full        28.34
_diffrn_measured_fraction_theta_full 0.994
_refine_diff_density_max         0.149
_refine_diff_density_min         -0.134
_refine_diff_density_rms         0.028