# Supplementary Material (ESI) for Chemical Communications
# This journal is (c) The Royal Society of Chemistry 2011
data_global

_journal_coden_Cambridge         182

loop_
_publ_author_name
'Luo, Yong'
'Hong, Linxiang'
'Wu, Jie'

_publ_contact_author_name        'Wu, Jie'
_publ_contact_author_email       jie_wu@fudan.edu.cn

_publ_section_title              
;
Efficient generation of indeno[1,2-c]chromenes via Pd-catalyzed
reaction of 2-alkynylhalobenzene with 2-alkynylphenol
;

# Attachment '- Uv.cif'

data_a01222c
_database_code_depnum_ccdc_archive 'CCDC 815061'
#TrackingRef '- Uv.cif'

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C28 H18 O'
_chemical_formula_weight         370.42

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                   8.384(3)
_cell_length_b                   10.466(3)
_cell_length_c                   10.991(4)
_cell_angle_alpha                89.811(4)
_cell_angle_beta                 78.202(4)
_cell_angle_gamma                87.135(4)
_cell_volume                     942.8(5)
_cell_formula_units_Z            2
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    725
_cell_measurement_theta_min      2.799
_cell_measurement_theta_max      20.444

_exptl_crystal_description       column
_exptl_crystal_colour            red
_exptl_crystal_size_max          0.20
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.12
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.305
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             388
_exptl_absorpt_coefficient_mu    0.078
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.9847
_exptl_absorpt_correction_T_max  0.9908
_exptl_absorpt_process_details   sadabs

_exptl_special_details           
;
?
;

_diffrn_ambient_temperature      293(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            6462
_diffrn_reflns_av_R_equivalents  0.0253
_diffrn_reflns_av_sigmaI/netI    0.0430
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       10
_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         1.89
_diffrn_reflns_theta_max         26.00
_reflns_number_total             3648
_reflns_number_gt                2543
_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^)+(0.0580P)^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    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         3648
_refine_ls_number_parameters     262
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0734
_refine_ls_R_factor_gt           0.0484
_refine_ls_wR_factor_ref         0.1161
_refine_ls_wR_factor_gt          0.1067
_refine_ls_goodness_of_fit_ref   0.979
_refine_ls_restrained_S_all      0.979
_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 0.23390(14) 0.61102(12) -0.04487(11) 0.0532(3) Uani 1 1 d . . .
C1 C 0.2609(2) 0.56421(17) 0.06726(15) 0.0441(4) Uani 1 1 d . . .
C2 C 0.1649(2) 0.46536(17) 0.11574(16) 0.0500(5) Uani 1 1 d . . .
H2 H 0.0874 0.4362 0.0742 0.060 Uiso 1 1 calc R . .
C3 C 0.1844(2) 0.41073(18) 0.22490(17) 0.0530(5) Uani 1 1 d . . .
H3 H 0.1216 0.3431 0.2576 0.064 Uiso 1 1 calc R . .
C4 C 0.2980(2) 0.45637(18) 0.28671(17) 0.0542(5) Uani 1 1 d . . .
H4 H 0.3113 0.4194 0.3613 0.065 Uiso 1 1 calc R . .
C5 C 0.3913(2) 0.55589(17) 0.23876(15) 0.0481(4) Uani 1 1 d . . .
H5 H 0.4668 0.5855 0.2820 0.058 Uiso 1 1 calc R . .
C6 C 0.37597(19) 0.61395(16) 0.12662(14) 0.0400(4) Uani 1 1 d . . .
C7 C 0.47513(19) 0.71383(15) 0.06441(14) 0.0390(4) Uani 1 1 d . . .
C8 C 0.60346(19) 0.77688(16) 0.09063(14) 0.0401(4) Uani 1 1 d . . .
C9 C 0.6751(2) 0.76890(16) 0.20275(15) 0.0400(4) Uani 1 1 d . . .
C10 C 0.5817(2) 0.79898(18) 0.31984(15) 0.0505(5) Uani 1 1 d . . .
H10 H 0.4730 0.8266 0.3273 0.061 Uiso 1 1 calc R . .
C11 C 0.6468(2) 0.7887(2) 0.42455(16) 0.0603(5) Uani 1 1 d . . .
H11 H 0.5814 0.8079 0.5020 0.072 Uiso 1 1 calc R . .
C12 C 0.8081(2) 0.75026(19) 0.41560(17) 0.0597(5) Uani 1 1 d . . .
H12 H 0.8521 0.7437 0.4866 0.072 Uiso 1 1 calc R . .
C13 C 0.9033(2) 0.72175(18) 0.30095(17) 0.0562(5) Uani 1 1 d . . .
H13 H 1.0125 0.6959 0.2941 0.067 Uiso 1 1 calc R . .
C14 C 0.8378(2) 0.73124(17) 0.19596(16) 0.0489(5) Uani 1 1 d . . .
H14 H 0.9040 0.7120 0.1188 0.059 Uiso 1 1 calc R . .
C15 C 0.66800(19) 0.85484(16) -0.01654(14) 0.0408(4) Uani 1 1 d . . .
C16 C 0.7998(2) 0.93207(18) -0.03846(16) 0.0517(5) Uani 1 1 d . . .
H16 H 0.8596 0.9435 0.0229 0.062 Uiso 1 1 calc R . .
C17 C 0.8423(2) 0.99179(19) -0.15086(17) 0.0577(5) Uani 1 1 d . . .
H17 H 0.9308 1.0438 -0.1655 0.069 Uiso 1 1 calc R . .
C18 C 0.7537(2) 0.97496(19) -0.24283(17) 0.0586(5) Uani 1 1 d . . .
H18 H 0.7853 1.0142 -0.3194 0.070 Uiso 1 1 calc R . .
C19 C 0.6203(2) 0.90116(17) -0.22221(16) 0.0494(5) Uani 1 1 d . . .
H19 H 0.5610 0.8914 -0.2842 0.059 Uiso 1 1 calc R . .
C20 C 0.57415(19) 0.84129(16) -0.10887(14) 0.0400(4) Uani 1 1 d . . .
C21 C 0.44836(19) 0.75286(16) -0.05840(14) 0.0399(4) Uani 1 1 d . . .
C22 C 0.3295(2) 0.70267(17) -0.10699(15) 0.0425(4) Uani 1 1 d . . .
C23 C 0.28174(19) 0.72937(17) -0.22668(15) 0.0442(4) Uani 1 1 d . . .
C24 C 0.2575(2) 0.85277(19) -0.26626(17) 0.0548(5) Uani 1 1 d . . .
H24 H 0.2721 0.9214 -0.2169 0.066 Uiso 1 1 calc R . .
C25 C 0.2119(2) 0.8752(2) -0.37817(19) 0.0661(6) Uani 1 1 d . . .
H25 H 0.1957 0.9588 -0.4037 0.079 Uiso 1 1 calc R . .
C26 C 0.1905(2) 0.7753(3) -0.45200(18) 0.0690(6) Uani 1 1 d . . .
H26 H 0.1616 0.7908 -0.5282 0.083 Uiso 1 1 calc R . .
C27 C 0.2116(2) 0.6524(2) -0.41337(17) 0.0651(6) Uani 1 1 d . . .
H27 H 0.1957 0.5844 -0.4631 0.078 Uiso 1 1 calc R . .
C28 C 0.2562(2) 0.62850(19) -0.30110(16) 0.0538(5) Uani 1 1 d . . .
H28 H 0.2693 0.5446 -0.2752 0.065 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
O1 0.0505(7) 0.0682(9) 0.0457(7) 0.0050(6) -0.0175(6) -0.0174(6)
C1 0.0419(10) 0.0530(11) 0.0366(9) -0.0013(8) -0.0065(8) -0.0013(8)
C2 0.0423(10) 0.0537(11) 0.0535(11) -0.0022(9) -0.0072(8) -0.0089(9)
C3 0.0513(11) 0.0500(11) 0.0545(11) 0.0030(9) -0.0025(9) -0.0078(9)
C4 0.0598(12) 0.0554(12) 0.0462(11) 0.0075(9) -0.0074(9) -0.0041(10)
C5 0.0514(11) 0.0517(11) 0.0428(10) 0.0000(8) -0.0121(8) -0.0061(9)
C6 0.0390(9) 0.0454(10) 0.0346(9) -0.0040(7) -0.0055(7) -0.0002(8)
C7 0.0392(9) 0.0467(10) 0.0310(8) -0.0025(7) -0.0077(7) -0.0001(8)
C8 0.0400(9) 0.0455(10) 0.0341(9) -0.0027(7) -0.0062(7) -0.0017(8)
C9 0.0424(9) 0.0415(10) 0.0379(9) 0.0019(7) -0.0105(7) -0.0086(8)
C10 0.0453(10) 0.0662(13) 0.0413(10) -0.0013(9) -0.0110(8) -0.0050(9)
C11 0.0609(13) 0.0841(15) 0.0370(10) -0.0031(9) -0.0109(9) -0.0096(11)
C12 0.0641(13) 0.0761(14) 0.0480(11) 0.0119(10) -0.0290(10) -0.0194(11)
C13 0.0472(11) 0.0660(13) 0.0601(12) 0.0048(10) -0.0218(9) -0.0049(9)
C14 0.0442(10) 0.0585(12) 0.0444(10) -0.0034(8) -0.0101(8) -0.0035(9)
C15 0.0413(9) 0.0454(10) 0.0351(9) -0.0043(7) -0.0071(7) -0.0005(8)
C16 0.0496(11) 0.0601(12) 0.0483(11) -0.0005(9) -0.0147(9) -0.0107(9)
C17 0.0499(11) 0.0654(13) 0.0589(12) 0.0116(10) -0.0101(9) -0.0188(10)
C18 0.0536(12) 0.0698(14) 0.0510(11) 0.0171(9) -0.0064(9) -0.0074(10)
C19 0.0500(11) 0.0607(12) 0.0390(10) 0.0060(8) -0.0122(8) -0.0049(9)
C20 0.0400(9) 0.0447(10) 0.0348(9) -0.0046(7) -0.0072(7) 0.0009(8)
C21 0.0390(9) 0.0457(10) 0.0348(9) -0.0034(7) -0.0079(7) 0.0001(8)
C22 0.0404(9) 0.0497(11) 0.0369(9) 0.0005(7) -0.0062(7) -0.0044(8)
C23 0.0354(9) 0.0597(12) 0.0382(9) -0.0021(8) -0.0086(7) -0.0049(8)
C24 0.0520(11) 0.0616(13) 0.0541(11) -0.0015(9) -0.0186(9) -0.0013(10)
C25 0.0583(13) 0.0806(16) 0.0641(13) 0.0204(12) -0.0232(11) -0.0058(11)
C26 0.0542(12) 0.112(2) 0.0466(12) 0.0149(12) -0.0210(10) -0.0213(12)
C27 0.0620(13) 0.0931(17) 0.0435(11) -0.0091(11) -0.0140(9) -0.0227(12)
C28 0.0515(11) 0.0636(13) 0.0491(11) -0.0025(9) -0.0145(9) -0.0127(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_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O1 C22 1.370(2) . ?
O1 C1 1.3817(19) . ?
C1 C2 1.381(2) . ?
C1 C6 1.392(2) . ?
C2 C3 1.364(2) . ?
C2 H2 0.9300 . ?
C3 C4 1.382(2) . ?
C3 H3 0.9300 . ?
C4 C5 1.373(2) . ?
C4 H4 0.9300 . ?
C5 C6 1.399(2) . ?
C5 H5 0.9300 . ?
C6 C7 1.450(2) . ?
C7 C8 1.369(2) . ?
C7 C21 1.466(2) . ?
C8 C15 1.457(2) . ?
C8 C9 1.477(2) . ?
C9 C14 1.388(2) . ?
C9 C10 1.391(2) . ?
C10 C11 1.372(2) . ?
C10 H10 0.9300 . ?
C11 C12 1.375(3) . ?
C11 H11 0.9300 . ?
C12 C13 1.372(3) . ?
C12 H12 0.9300 . ?
C13 C14 1.377(2) . ?
C13 H13 0.9300 . ?
C14 H14 0.9300 . ?
C15 C16 1.383(2) . ?
C15 C20 1.417(2) . ?
C16 C17 1.371(2) . ?
C16 H16 0.9300 . ?
C17 C18 1.387(2) . ?
C17 H17 0.9300 . ?
C18 C19 1.372(3) . ?
C18 H18 0.9300 . ?
C19 C20 1.384(2) . ?
C19 H19 0.9300 . ?
C20 C21 1.460(2) . ?
C21 C22 1.351(2) . ?
C22 C23 1.473(2) . ?
C23 C24 1.380(2) . ?
C23 C28 1.389(2) . ?
C24 C25 1.377(2) . ?
C24 H24 0.9300 . ?
C25 C26 1.367(3) . ?
C25 H25 0.9300 . ?
C26 C27 1.368(3) . ?
C26 H26 0.9300 . ?
C27 C28 1.379(2) . ?
C27 H27 0.9300 . ?
C28 H28 0.9300 . ?

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
C22 O1 C1 120.59(13) . . ?
C2 C1 O1 114.99(15) . . ?
C2 C1 C6 122.84(16) . . ?
O1 C1 C6 122.17(15) . . ?
C3 C2 C1 119.56(17) . . ?
C3 C2 H2 120.2 . . ?
C1 C2 H2 120.2 . . ?
C2 C3 C4 119.62(17) . . ?
C2 C3 H3 120.2 . . ?
C4 C3 H3 120.2 . . ?
C5 C4 C3 120.44(17) . . ?
C5 C4 H4 119.8 . . ?
C3 C4 H4 119.8 . . ?
C4 C5 C6 121.74(17) . . ?
C4 C5 H5 119.1 . . ?
C6 C5 H5 119.1 . . ?
C1 C6 C5 115.79(16) . . ?
C1 C6 C7 118.07(14) . . ?
C5 C6 C7 126.01(15) . . ?
C8 C7 C6 133.61(15) . . ?
C8 C7 C21 109.16(14) . . ?
C6 C7 C21 116.99(14) . . ?
C7 C8 C15 107.92(13) . . ?
C7 C8 C9 128.90(15) . . ?
C15 C8 C9 123.15(14) . . ?
C14 C9 C10 117.16(15) . . ?
C14 C9 C8 121.63(15) . . ?
C10 C9 C8 121.20(15) . . ?
C11 C10 C9 121.38(17) . . ?
C11 C10 H10 119.3 . . ?
C9 C10 H10 119.3 . . ?
C10 C11 C12 120.38(18) . . ?
C10 C11 H11 119.8 . . ?
C12 C11 H11 119.8 . . ?
C13 C12 C11 119.36(17) . . ?
C13 C12 H12 120.3 . . ?
C11 C12 H12 120.3 . . ?
C12 C13 C14 120.27(18) . . ?
C12 C13 H13 119.9 . . ?
C14 C13 H13 119.9 . . ?
C13 C14 C9 121.42(17) . . ?
C13 C14 H14 119.3 . . ?
C9 C14 H14 119.3 . . ?
C16 C15 C20 119.76(16) . . ?
C16 C15 C8 130.62(15) . . ?
C20 C15 C8 109.61(14) . . ?
C17 C16 C15 119.88(16) . . ?
C17 C16 H16 120.1 . . ?
C15 C16 H16 120.1 . . ?
C16 C17 C18 120.32(18) . . ?
C16 C17 H17 119.8 . . ?
C18 C17 H17 119.8 . . ?
C19 C18 C17 120.83(17) . . ?
C19 C18 H18 119.6 . . ?
C17 C18 H18 119.6 . . ?
C18 C19 C20 119.77(16) . . ?
C18 C19 H19 120.1 . . ?
C20 C19 H19 120.1 . . ?
C19 C20 C15 119.37(16) . . ?
C19 C20 C21 134.34(15) . . ?
C15 C20 C21 106.13(14) . . ?
C22 C21 C20 131.91(15) . . ?
C22 C21 C7 120.87(15) . . ?
C20 C21 C7 107.13(13) . . ?
C21 C22 O1 121.07(15) . . ?
C21 C22 C23 129.43(16) . . ?
O1 C22 C23 109.48(14) . . ?
C24 C23 C28 118.55(16) . . ?
C24 C23 C22 121.76(16) . . ?
C28 C23 C22 119.67(17) . . ?
C25 C24 C23 120.64(18) . . ?
C25 C24 H24 119.7 . . ?
C23 C24 H24 119.7 . . ?
C26 C25 C24 120.4(2) . . ?
C26 C25 H25 119.8 . . ?
C24 C25 H25 119.8 . . ?
C25 C26 C27 119.77(19) . . ?
C25 C26 H26 120.1 . . ?
C27 C26 H26 120.1 . . ?
C26 C27 C28 120.5(2) . . ?
C26 C27 H27 119.8 . . ?
C28 C27 H27 119.8 . . ?
C27 C28 C23 120.17(19) . . ?
C27 C28 H28 119.9 . . ?
C23 C28 H28 119.9 . . ?

_diffrn_measured_fraction_theta_max 0.983
_diffrn_reflns_theta_full        26.00
_diffrn_measured_fraction_theta_full 0.983
_refine_diff_density_max         0.130
_refine_diff_density_min         -0.174
_refine_diff_density_rms         0.034