# 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        'Youhong Hu'
_publ_contact_author_address     
;
Shanghai Institute of Materia Medica
555 Zuchongzhi Rd
Shanghai
201203
CHINA
;

_publ_contact_author_email       YHHU@MAIL.SHCNC.AC.CN

_publ_section_title              
;
One-pot Synthesis of Furocoumarins through Cascade
Addition-Cyclization-Oxidation
;
loop_
_publ_author_name
'Youhong Hu'
'Gang Cheng'

data_cd26248
_database_code_depnum_ccdc_archive 'CCDC 622672'

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C17 H10 O3'
_chemical_formula_weight         262.25

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           Monoclinic
_symmetry_space_group_name_H-M   P2(1)/c

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

_cell_length_a                   12.695(2)
_cell_length_b                   7.0754(11)
_cell_length_c                   14.000(2)
_cell_angle_alpha                90.00
_cell_angle_beta                 99.352(3)
_cell_angle_gamma                90.00
_cell_volume                     1240.8(3)
_cell_formula_units_Z            4
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    1070
_cell_measurement_theta_min      5.898
_cell_measurement_theta_max      44.304

_exptl_crystal_description       prismatic
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.421
_exptl_crystal_size_mid          0.121
_exptl_crystal_size_min          0.064
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.404
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             544
_exptl_absorpt_coefficient_mu    0.096
_exptl_absorpt_correction_type   empirical
_exptl_absorpt_correction_T_min  0.75182
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_process_details   ?

_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            7044
_diffrn_reflns_av_R_equivalents  0.1179
_diffrn_reflns_av_sigmaI/netI    0.1165
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_theta_min         1.63
_diffrn_reflns_theta_max         27.00
_reflns_number_total             2693
_reflns_number_gt                1422
_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^)+(0.0808P)^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         2693
_refine_ls_number_parameters     181
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1050
_refine_ls_R_factor_gt           0.0583
_refine_ls_wR_factor_ref         0.1726
_refine_ls_wR_factor_gt          0.1379
_refine_ls_goodness_of_fit_ref   0.873
_refine_ls_restrained_S_all      0.873
_refine_ls_shift/su_max          0.021
_refine_ls_shift/su_mean         0.003

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 0.81733(15) 0.0694(3) 0.44702(13) 0.0694(6) Uani 1 1 d . . .
O2 O 0.68228(14) 0.1078(2) 0.52714(12) 0.0538(5) Uani 1 1 d . . .
O3 O 0.89227(12) 0.1238(2) 0.77883(11) 0.0429(5) Uani 1 1 d . . .
C1 C 0.7910(2) 0.0905(4) 0.52489(18) 0.0492(7) Uani 1 1 d . . .
C2 C 0.85843(19) 0.0991(3) 0.61872(17) 0.0430(6) Uani 1 1 d . . .
C3 C 0.81518(19) 0.1193(3) 0.69967(17) 0.0403(6) Uani 1 1 d . . .
C4 C 0.70445(18) 0.1399(3) 0.70218(17) 0.0413(6) Uani 1 1 d . . .
C5 C 0.6406(2) 0.1356(3) 0.61105(18) 0.0450(6) Uani 1 1 d . . .
C6 C 0.5317(2) 0.1640(4) 0.6010(2) 0.0551(7) Uani 1 1 d . . .
H6 H 0.4896 0.1616 0.5401 0.066 Uiso 1 1 calc R . .
C7 C 0.4862(2) 0.1958(4) 0.6824(2) 0.0611(8) Uani 1 1 d . . .
H7 H 0.4128 0.2132 0.6763 0.073 Uiso 1 1 calc R . .
C8 C 0.5481(2) 0.2022(4) 0.7731(2) 0.0605(8) Uani 1 1 d . . .
H8 H 0.5163 0.2250 0.8273 0.073 Uiso 1 1 calc R . .
C9 C 0.6566(2) 0.1750(4) 0.78325(19) 0.0513(7) Uani 1 1 d . . .
H9 H 0.6981 0.1800 0.8444 0.062 Uiso 1 1 calc R . .
C10 C 0.9705(2) 0.0907(3) 0.64715(18) 0.0450(6) Uani 1 1 d . . .
H10 H 1.0214 0.0766 0.6068 0.054 Uiso 1 1 calc R . .
C11 C 0.98902(19) 0.1072(3) 0.74435(17) 0.0404(6) Uani 1 1 d . . .
C12 C 1.08428(18) 0.1071(3) 0.81806(17) 0.0401(6) Uani 1 1 d . . .
C13 C 1.0771(2) 0.1176(3) 0.91578(18) 0.0495(7) Uani 1 1 d . . .
H13 H 1.0105 0.1280 0.9349 0.059 Uiso 1 1 calc R . .
C14 C 1.1681(2) 0.1127(4) 0.9850(2) 0.0583(7) Uani 1 1 d . . .
H14 H 1.1627 0.1186 1.0503 0.070 Uiso 1 1 calc R . .
C15 C 1.2671(2) 0.0991(4) 0.9569(2) 0.0602(8) Uani 1 1 d . . .
H15 H 1.3284 0.0949 1.0033 0.072 Uiso 1 1 calc R . .
C16 C 1.2750(2) 0.0917(4) 0.8605(2) 0.0590(8) Uani 1 1 d . . .
H16 H 1.3420 0.0849 0.8419 0.071 Uiso 1 1 calc R . .
C17 C 1.1848(2) 0.0943(4) 0.7906(2) 0.0511(7) Uani 1 1 d . . .
H17 H 1.1911 0.0876 0.7254 0.061 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 0.0636(13) 0.1114(17) 0.0324(10) 0.0019(10) 0.0055(9) 0.0220(11)
O2 0.0452(11) 0.0740(13) 0.0394(10) -0.0060(9) -0.0012(8) 0.0080(9)
O3 0.0362(10) 0.0587(11) 0.0333(9) -0.0026(7) 0.0036(7) 0.0013(8)
C1 0.0475(17) 0.0622(18) 0.0371(15) -0.0003(12) 0.0045(12) 0.0098(13)
C2 0.0401(14) 0.0508(16) 0.0375(14) 0.0003(11) 0.0045(11) 0.0056(11)
C3 0.0391(14) 0.0454(15) 0.0348(13) -0.0020(10) 0.0011(11) -0.0011(11)
C4 0.0366(14) 0.0459(15) 0.0403(14) -0.0030(11) 0.0032(11) 0.0000(11)
C5 0.0425(15) 0.0491(16) 0.0424(15) -0.0060(12) 0.0040(12) 0.0030(11)
C6 0.0405(16) 0.0645(18) 0.0560(17) -0.0078(14) -0.0047(13) 0.0021(13)
C7 0.0359(15) 0.072(2) 0.074(2) -0.0072(16) 0.0065(15) 0.0008(13)
C8 0.0480(18) 0.075(2) 0.0615(19) -0.0086(15) 0.0180(15) -0.0028(14)
C9 0.0422(16) 0.0640(18) 0.0472(16) -0.0059(13) 0.0061(12) -0.0042(13)
C10 0.0417(15) 0.0572(16) 0.0375(14) 0.0026(11) 0.0111(11) 0.0056(12)
C11 0.0360(14) 0.0464(15) 0.0393(14) -0.0002(11) 0.0083(11) 0.0020(11)
C12 0.0375(14) 0.0393(14) 0.0433(15) -0.0016(11) 0.0065(11) -0.0020(10)
C13 0.0412(15) 0.0624(17) 0.0440(15) 0.0007(13) 0.0048(12) -0.0041(12)
C14 0.0547(18) 0.073(2) 0.0439(15) -0.0003(14) -0.0006(13) -0.0045(14)
C15 0.0471(17) 0.068(2) 0.0592(19) -0.0002(15) -0.0095(14) -0.0060(14)
C16 0.0368(16) 0.071(2) 0.068(2) -0.0023(15) 0.0071(14) -0.0033(13)
C17 0.0435(16) 0.0603(17) 0.0495(16) -0.0028(12) 0.0078(13) -0.0009(12)

_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 1.200(3) . ?
O2 C5 1.378(3) . ?
O2 C1 1.391(3) . ?
O3 C3 1.355(3) . ?
O3 C11 1.396(3) . ?
C1 C2 1.448(3) . ?
C2 C3 1.345(3) . ?
C2 C10 1.415(3) . ?
C3 C4 1.419(3) . ?
C4 C9 1.394(3) . ?
C4 C5 1.396(3) . ?
C5 C6 1.382(3) . ?
C6 C7 1.378(4) . ?
C6 H6 0.9300 . ?
C7 C8 1.380(4) . ?
C7 H7 0.9300 . ?
C8 C9 1.375(3) . ?
C8 H8 0.9300 . ?
C9 H9 0.9300 . ?
C10 C11 1.348(3) . ?
C10 H10 0.9300 . ?
C11 C12 1.457(3) . ?
C12 C13 1.388(3) . ?
C12 C17 1.395(3) . ?
C13 C14 1.383(4) . ?
C13 H13 0.9300 . ?
C14 C15 1.379(4) . ?
C14 H14 0.9300 . ?
C15 C16 1.371(4) . ?
C15 H15 0.9300 . ?
C16 C17 1.380(4) . ?
C16 H16 0.9300 . ?
C17 H17 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
C5 O2 C1 123.4(2) . . ?
C3 O3 C11 105.93(17) . . ?
O1 C1 O2 117.1(2) . . ?
O1 C1 C2 128.2(2) . . ?
O2 C1 C2 114.7(2) . . ?
C3 C2 C10 107.3(2) . . ?
C3 C2 C1 120.4(2) . . ?
C10 C2 C1 132.3(2) . . ?
C2 C3 O3 110.6(2) . . ?
C2 C3 C4 125.0(2) . . ?
O3 C3 C4 124.3(2) . . ?
C9 C4 C5 118.9(2) . . ?
C9 C4 C3 127.1(2) . . ?
C5 C4 C3 113.9(2) . . ?
O2 C5 C6 116.7(2) . . ?
O2 C5 C4 122.4(2) . . ?
C6 C5 C4 120.8(2) . . ?
C7 C6 C5 119.1(3) . . ?
C7 C6 H6 120.5 . . ?
C5 C6 H6 120.5 . . ?
C6 C7 C8 120.9(2) . . ?
C6 C7 H7 119.5 . . ?
C8 C7 H7 119.5 . . ?
C9 C8 C7 120.1(3) . . ?
C9 C8 H8 119.9 . . ?
C7 C8 H8 119.9 . . ?
C8 C9 C4 120.1(2) . . ?
C8 C9 H9 119.9 . . ?
C4 C9 H9 119.9 . . ?
C11 C10 C2 106.4(2) . . ?
C11 C10 H10 126.8 . . ?
C2 C10 H10 126.8 . . ?
C10 C11 O3 109.7(2) . . ?
C10 C11 C12 134.7(2) . . ?
O3 C11 C12 115.5(2) . . ?
C13 C12 C17 119.0(2) . . ?
C13 C12 C11 121.2(2) . . ?
C17 C12 C11 119.7(2) . . ?
C14 C13 C12 120.5(2) . . ?
C14 C13 H13 119.7 . . ?
C12 C13 H13 119.7 . . ?
C15 C14 C13 119.9(3) . . ?
C15 C14 H14 120.1 . . ?
C13 C14 H14 120.1 . . ?
C16 C15 C14 119.9(3) . . ?
C16 C15 H15 120.0 . . ?
C14 C15 H15 120.0 . . ?
C15 C16 C17 120.9(3) . . ?
C15 C16 H16 119.6 . . ?
C17 C16 H16 119.6 . . ?
C16 C17 C12 119.7(2) . . ?
C16 C17 H17 120.1 . . ?
C12 C17 H17 120.1 . . ?

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
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C5 O2 C1 O1 -178.9(2) . . . . ?
C5 O2 C1 C2 1.5(3) . . . . ?
O1 C1 C2 C3 -178.4(3) . . . . ?
O2 C1 C2 C3 1.0(4) . . . . ?
O1 C1 C2 C10 1.8(5) . . . . ?
O2 C1 C2 C10 -178.8(2) . . . . ?
C10 C2 C3 O3 -0.2(3) . . . . ?
C1 C2 C3 O3 179.9(2) . . . . ?
C10 C2 C3 C4 177.7(2) . . . . ?
C1 C2 C3 C4 -2.2(4) . . . . ?
C11 O3 C3 C2 0.6(3) . . . . ?
C11 O3 C3 C4 -177.3(2) . . . . ?
C2 C3 C4 C9 -174.9(2) . . . . ?
O3 C3 C4 C9 2.7(4) . . . . ?
C2 C3 C4 C5 0.7(4) . . . . ?
O3 C3 C4 C5 178.3(2) . . . . ?
C1 O2 C5 C6 175.4(2) . . . . ?
C1 O2 C5 C4 -3.2(4) . . . . ?
C9 C4 C5 O2 177.9(2) . . . . ?
C3 C4 C5 O2 1.9(3) . . . . ?
C9 C4 C5 C6 -0.5(4) . . . . ?
C3 C4 C5 C6 -176.5(2) . . . . ?
O2 C5 C6 C7 -178.9(2) . . . . ?
C4 C5 C6 C7 -0.3(4) . . . . ?
C5 C6 C7 C8 0.9(4) . . . . ?
C6 C7 C8 C9 -0.6(4) . . . . ?
C7 C8 C9 C4 -0.3(4) . . . . ?
C5 C4 C9 C8 0.8(4) . . . . ?
C3 C4 C9 C8 176.3(2) . . . . ?
C3 C2 C10 C11 -0.3(3) . . . . ?
C1 C2 C10 C11 179.6(3) . . . . ?
C2 C10 C11 O3 0.6(3) . . . . ?
C2 C10 C11 C12 179.0(2) . . . . ?
C3 O3 C11 C10 -0.8(3) . . . . ?
C3 O3 C11 C12 -179.49(19) . . . . ?
C10 C11 C12 C13 -176.6(3) . . . . ?
O3 C11 C12 C13 1.7(3) . . . . ?
C10 C11 C12 C17 2.8(4) . . . . ?
O3 C11 C12 C17 -178.9(2) . . . . ?
C17 C12 C13 C14 -0.9(4) . . . . ?
C11 C12 C13 C14 178.4(2) . . . . ?
C12 C13 C14 C15 0.6(4) . . . . ?
C13 C14 C15 C16 0.4(4) . . . . ?
C14 C15 C16 C17 -1.2(4) . . . . ?
C15 C16 C17 C12 0.9(4) . . . . ?
C13 C12 C17 C16 0.2(4) . . . . ?
C11 C12 C17 C16 -179.1(2) . . . . ?

_diffrn_measured_fraction_theta_max 0.996
_diffrn_reflns_theta_full        27.00
_diffrn_measured_fraction_theta_full 0.996
_refine_diff_density_max         0.191
_refine_diff_density_min         -0.307
_refine_diff_density_rms         0.062