Supplementary Material (ESI) for Photochemical & Photobiological Sciences
This journal is © The Royal Society of Chemistry and Owner Societies 2009

data_global
_journal_name_full               Photochem.Photobiol.Sci.

_journal_coden_Cambridge         0171

_publ_contact_author_name        'Jian-Hua Xu'
_publ_contact_author_email       XUJH@NJU.EDU.CN

_publ_section_title              
;
Photo-multicomponent reactions leading to the
construction of isocoumarins and large ring lactone precursors
;
loop_
_publ_author_name
'Jian-Hua Xu.'
'Hongwen Hu.'
'Zhi-Feng Lu.'
'Jia-Jun Yue.'
'Ye Zhu.'

# Attachment 'CCDC 683621.CIF'

data_683621
_database_code_depnum_ccdc_archive 'CCDC 683621'

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
(4R,6S)-4,6-dimethyl-4,6-diphenyl-3,4,6,7-
tetrahydropyrano[4,3-g]isochromene-1,9-dione
;
_chemical_name_common            
;
(4R,6S)-4,6-dimethyl-4,6-diphenyl-3,4,6,7-
tetrahydropyrano(4,3-g)isochromene-1,9-dione
;
_chemical_melting_point          533.2
_chemical_formula_moiety         'C26 H22 O4'
_chemical_formula_sum            'C26 H22 O4'
_chemical_formula_weight         398.44

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   'P 21/c'
_symmetry_space_group_name_Hall  '-P 2ybc'

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                   12.751(3)
_cell_length_b                   7.8730(16)
_cell_length_c                   20.264(4)
_cell_angle_alpha                90.00
_cell_angle_beta                 103.84(3)
_cell_angle_gamma                90.00
_cell_volume                     1975.2(8)
_cell_formula_units_Z            4
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    25
_cell_measurement_theta_min      10
_cell_measurement_theta_max      13

_exptl_crystal_description       block
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.34
_exptl_crystal_size_mid          0.22
_exptl_crystal_size_min          0.20
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.340
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             840
_exptl_absorpt_coefficient_mu    0.090
_exptl_absorpt_correction_type   psi-scan
_exptl_absorpt_correction_T_min  0.956
_exptl_absorpt_correction_T_max  0.982
_exptl_absorpt_process_details   '(XCAD4; Harms & Wocadlo, 1995)'

_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  'Enraf--Nonius CAD-4'
_diffrn_measurement_method       \w/2\q
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         3
_diffrn_standards_interval_count 200
_diffrn_standards_interval_time  120
_diffrn_standards_decay_%        0
_diffrn_reflns_number            4053
_diffrn_reflns_av_R_equivalents  0.0213
_diffrn_reflns_av_sigmaI/netI    0.0563
_diffrn_reflns_limit_h_min       0
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_k_min       0
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_l_min       -24
_diffrn_reflns_limit_l_max       24
_diffrn_reflns_theta_min         1.64
_diffrn_reflns_theta_max         25.97
_reflns_number_total             3872
_reflns_number_gt                2343
_reflns_threshold_expression     I>2\s(I)

_computing_data_collection       'CAD4 Software (Enraf-Nonius, 1989)'
_computing_cell_refinement       'CAD4 Software'
_computing_data_reduction        'XCAD4 (Harms & Wocadlo, 1995)'
_computing_structure_solution    'SHELXTL (Sheldrick, 1997)'
_computing_structure_refinement  SHELXTL
_computing_molecular_graphics    SHELXTL
_computing_publication_material  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^)+(0.06P)^2^+0.98P] 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         3872
_refine_ls_number_parameters     271
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1073
_refine_ls_R_factor_gt           0.0561
_refine_ls_wR_factor_ref         0.1530
_refine_ls_wR_factor_gt          0.1280
_refine_ls_goodness_of_fit_ref   1.000
_refine_ls_restrained_S_all      1.000
_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 0.32928(17) 0.6259(3) 0.34411(10) 0.0598(6) Uani 1 1 d . . .
O2 O 0.62538(15) 0.6970(3) 0.55942(10) 0.0547(6) Uani 1 1 d . . .
O3 O 0.16249(15) 0.6079(3) 0.35547(9) 0.0465(5) Uani 1 1 d . . .
O4 O 0.59665(14) 0.8765(3) 0.63551(9) 0.0480(5) Uani 1 1 d . . .
C1 C 0.2681(2) 0.6435(4) 0.38030(13) 0.0418(7) Uani 1 1 d . . .
C2 C 0.0949(2) 0.6090(4) 0.40293(14) 0.0445(7) Uani 1 1 d . . .
H2A H 0.1135 0.5128 0.4333 0.053 Uiso 1 1 calc R . .
H2B H 0.0202 0.5959 0.3782 0.053 Uiso 1 1 calc R . .
C3 C 0.1058(2) 0.7709(3) 0.44470(12) 0.0348(6) Uani 1 1 d . . .
C4 C 0.22481(19) 0.7819(3) 0.48206(12) 0.0323(6) Uani 1 1 d . . .
C5 C 0.26104(19) 0.8619(3) 0.54430(12) 0.0338(6) Uani 1 1 d . . .
H5 H 0.2110 0.9103 0.5654 0.041 Uiso 1 1 calc R . .
C6 C 0.37042(19) 0.8716(3) 0.57604(12) 0.0314(6) Uani 1 1 d . . .
C7 C 0.41172(19) 0.9590(3) 0.64418(12) 0.0332(6) Uani 1 1 d . . .
C8 C 0.5288(2) 1.0130(4) 0.64853(14) 0.0424(7) Uani 1 1 d . . .
H8A H 0.5289 1.1032 0.6159 0.051 Uiso 1 1 calc R . .
H8B H 0.5594 1.0584 0.6935 0.051 Uiso 1 1 calc R . .
C9 C 0.5622(2) 0.7850(4) 0.57928(13) 0.0393(6) Uani 1 1 d . . .
C10 C 0.44462(19) 0.7921(3) 0.54540(12) 0.0326(6) Uani 1 1 d . . .
C11 C 0.4097(2) 0.7130(3) 0.48296(12) 0.0361(6) Uani 1 1 d . . .
H11 H 0.4595 0.6608 0.4627 0.043 Uiso 1 1 calc R . .
C12 C 0.3007(2) 0.7115(3) 0.45050(12) 0.0344(6) Uani 1 1 d . . .
C13 C 0.0719(2) 0.9236(3) 0.39821(12) 0.0355(6) Uani 1 1 d . . .
C14 C -0.0349(2) 0.9348(4) 0.35868(13) 0.0462(7) Uani 1 1 d . . .
H14 H -0.0842 0.8507 0.3626 0.055 Uiso 1 1 calc R . .
C15 C -0.0675(2) 1.0667(4) 0.31471(15) 0.0559(8) Uani 1 1 d . . .
H15 H -0.1382 1.0700 0.2886 0.067 Uiso 1 1 calc R . .
C16 C 0.0030(3) 1.1944(4) 0.30868(15) 0.0559(8) Uani 1 1 d . . .
H16 H -0.0194 1.2842 0.2788 0.067 Uiso 1 1 calc R . .
C17 C 0.1087(2) 1.1871(4) 0.34813(15) 0.0497(7) Uani 1 1 d . . .
H17 H 0.1572 1.2731 0.3448 0.060 Uiso 1 1 calc R . .
C18 C 0.1416(2) 1.0538(3) 0.39193(14) 0.0410(7) Uani 1 1 d . . .
H18 H 0.2124 1.0511 0.4179 0.049 Uiso 1 1 calc R . .
C19 C 0.0334(2) 0.7500(4) 0.49517(14) 0.0464(7) Uani 1 1 d . . .
H19A H 0.0375 0.8508 0.5224 0.070 Uiso 1 1 calc R . .
H19B H 0.0576 0.6542 0.5241 0.070 Uiso 1 1 calc R . .
H19C H -0.0400 0.7321 0.4705 0.070 Uiso 1 1 calc R . .
C20 C 0.34975(19) 1.1242(3) 0.64902(12) 0.0336(6) Uani 1 1 d . . .
C21 C 0.3291(2) 1.2370(4) 0.59457(14) 0.0449(7) Uani 1 1 d . . .
H21 H 0.3499 1.2080 0.5550 0.054 Uiso 1 1 calc R . .
C22 C 0.2793(3) 1.3891(4) 0.59775(16) 0.0542(8) Uani 1 1 d . . .
H22 H 0.2671 1.4629 0.5608 0.065 Uiso 1 1 calc R . .
C23 C 0.2470(2) 1.4336(4) 0.65596(17) 0.0543(8) Uani 1 1 d . . .
H23 H 0.2119 1.5363 0.6582 0.065 Uiso 1 1 calc R . .
C24 C 0.2671(2) 1.3253(4) 0.70991(16) 0.0508(8) Uani 1 1 d . . .
H24 H 0.2460 1.3553 0.7492 0.061 Uiso 1 1 calc R . .
C25 C 0.3183(2) 1.1715(4) 0.70737(13) 0.0401(7) Uani 1 1 d . . .
H25 H 0.3316 1.0996 0.7449 0.048 Uiso 1 1 calc R . .
C26 C 0.4088(2) 0.8309(4) 0.70045(13) 0.0441(7) Uani 1 1 d . . .
H26A H 0.4490 0.7314 0.6943 0.066 Uiso 1 1 calc R . .
H26B H 0.3353 0.7999 0.6985 0.066 Uiso 1 1 calc R . .
H26C H 0.4404 0.8809 0.7439 0.066 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 0.0618(14) 0.0842(17) 0.0392(11) -0.0167(11) 0.0239(10) -0.0155(12)
O2 0.0346(11) 0.0751(15) 0.0549(12) -0.0038(11) 0.0118(9) 0.0094(11)
O3 0.0470(12) 0.0559(12) 0.0344(10) -0.0104(9) 0.0053(9) -0.0123(10)
O4 0.0274(9) 0.0735(14) 0.0405(11) -0.0092(10) 0.0028(8) 0.0000(10)
C1 0.0495(17) 0.0430(16) 0.0323(14) -0.0030(12) 0.0087(13) -0.0080(14)
C2 0.0397(15) 0.0487(17) 0.0439(16) -0.0062(13) 0.0077(13) -0.0135(13)
C3 0.0279(13) 0.0427(15) 0.0324(13) -0.0021(11) 0.0043(10) -0.0095(11)
C4 0.0303(13) 0.0351(14) 0.0309(13) 0.0007(11) 0.0062(10) -0.0068(11)
C5 0.0285(13) 0.0410(15) 0.0323(13) -0.0012(11) 0.0083(10) -0.0032(11)
C6 0.0309(13) 0.0360(14) 0.0272(12) 0.0013(11) 0.0068(10) -0.0047(11)
C7 0.0284(13) 0.0434(15) 0.0274(12) -0.0013(11) 0.0059(10) -0.0056(11)
C8 0.0330(14) 0.0536(18) 0.0401(15) -0.0064(13) 0.0077(12) -0.0070(13)
C9 0.0306(14) 0.0532(17) 0.0358(14) 0.0025(13) 0.0111(11) -0.0002(13)
C10 0.0289(13) 0.0404(15) 0.0295(13) 0.0041(11) 0.0090(10) -0.0006(11)
C11 0.0333(14) 0.0421(15) 0.0353(14) 0.0014(12) 0.0129(11) 0.0002(12)
C12 0.0362(14) 0.0380(14) 0.0288(13) -0.0006(11) 0.0076(11) -0.0056(12)
C13 0.0320(13) 0.0426(15) 0.0319(13) -0.0044(12) 0.0077(11) -0.0047(12)
C14 0.0333(15) 0.061(2) 0.0407(15) 0.0023(14) 0.0027(12) -0.0095(14)
C15 0.0410(17) 0.077(2) 0.0465(18) 0.0106(17) 0.0041(13) 0.0028(16)
C16 0.058(2) 0.060(2) 0.0491(18) 0.0143(16) 0.0128(15) 0.0127(17)
C17 0.0475(18) 0.0469(18) 0.0584(18) 0.0068(15) 0.0199(15) -0.0038(14)
C18 0.0317(14) 0.0454(16) 0.0460(16) -0.0002(13) 0.0091(12) -0.0041(12)
C19 0.0342(15) 0.0588(19) 0.0449(16) 0.0045(14) 0.0072(12) -0.0129(13)
C20 0.0279(13) 0.0412(15) 0.0307(13) -0.0046(11) 0.0052(10) -0.0097(11)
C21 0.0489(17) 0.0479(18) 0.0386(15) 0.0016(13) 0.0116(13) -0.0060(14)
C22 0.063(2) 0.0415(18) 0.0555(19) 0.0078(15) 0.0085(16) -0.0043(15)
C23 0.0421(17) 0.0418(17) 0.075(2) -0.0125(17) 0.0059(16) -0.0024(14)
C24 0.0376(16) 0.062(2) 0.0523(18) -0.0196(16) 0.0102(13) -0.0058(15)
C25 0.0313(14) 0.0561(18) 0.0312(14) -0.0040(13) 0.0044(11) -0.0078(13)
C26 0.0450(16) 0.0534(18) 0.0345(14) 0.0056(13) 0.0106(12) -0.0005(14)

_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 C9 1.203(3) . ?
O3 C1 1.349(3) . ?
O3 C2 1.437(3) . ?
O4 C9 1.330(3) . ?
O4 C8 1.443(3) . ?
C1 C12 1.483(3) . ?
C2 C3 1.518(4) . ?
C2 H2A 0.9700 . ?
C2 H2B 0.9700 . ?
C3 C13 1.525(4) . ?
C3 C4 1.528(3) . ?
C3 C19 1.541(4) . ?
C4 C5 1.386(3) . ?
C4 C12 1.396(4) . ?
C5 C6 1.391(3) . ?
C5 H5 0.9300 . ?
C6 C10 1.398(3) . ?
C6 C7 1.520(3) . ?
C7 C26 1.530(3) . ?
C7 C8 1.534(3) . ?
C7 C20 1.537(4) . ?
C8 H8A 0.9700 . ?
C8 H8B 0.9700 . ?
C9 C10 1.493(3) . ?
C10 C11 1.385(3) . ?
C11 C12 1.388(3) . ?
C11 H11 0.9300 . ?
C13 C18 1.383(4) . ?
C13 C14 1.407(4) . ?
C14 C15 1.367(4) . ?
C14 H14 0.9300 . ?
C15 C16 1.374(4) . ?
C15 H15 0.9300 . ?
C16 C17 1.394(4) . ?
C16 H16 0.9300 . ?
C17 C18 1.374(4) . ?
C17 H17 0.9300 . ?
C18 H18 0.9300 . ?
C19 H19A 0.9600 . ?
C19 H19B 0.9600 . ?
C19 H19C 0.9600 . ?
C20 C25 1.388(3) . ?
C20 C21 1.392(4) . ?
C21 C22 1.364(4) . ?
C21 H21 0.9300 . ?
C22 C23 1.385(4) . ?
C22 H22 0.9300 . ?
C23 C24 1.362(4) . ?
C23 H23 0.9300 . ?
C24 C25 1.382(4) . ?
C24 H24 0.9300 . ?
C25 H25 0.9300 . ?
C26 H26A 0.9600 . ?
C26 H26B 0.9600 . ?
C26 H26C 0.9600 . ?

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
C1 O3 C2 117.0(2) . . ?
C9 O4 C8 118.0(2) . . ?
O1 C1 O3 119.0(2) . . ?
O1 C1 C12 123.6(3) . . ?
O3 C1 C12 117.3(2) . . ?
O3 C2 C3 112.9(2) . . ?
O3 C2 H2A 109.0 . . ?
C3 C2 H2A 109.0 . . ?
O3 C2 H2B 109.0 . . ?
C3 C2 H2B 109.0 . . ?
H2A C2 H2B 107.8 . . ?
C2 C3 C13 110.1(2) . . ?
C2 C3 C4 105.8(2) . . ?
C13 C3 C4 111.2(2) . . ?
C2 C3 C19 106.9(2) . . ?
C13 C3 C19 111.6(2) . . ?
C4 C3 C19 111.0(2) . . ?
C5 C4 C12 118.7(2) . . ?
C5 C4 C3 123.5(2) . . ?
C12 C4 C3 117.8(2) . . ?
C4 C5 C6 121.6(2) . . ?
C4 C5 H5 119.2 . . ?
C6 C5 H5 119.2 . . ?
C5 C6 C10 118.7(2) . . ?
C5 C6 C7 122.4(2) . . ?
C10 C6 C7 118.8(2) . . ?
C6 C7 C26 108.3(2) . . ?
C6 C7 C8 107.4(2) . . ?
C26 C7 C8 109.7(2) . . ?
C6 C7 C20 111.7(2) . . ?
C26 C7 C20 113.9(2) . . ?
C8 C7 C20 105.7(2) . . ?
O4 C8 C7 113.6(2) . . ?
O4 C8 H8A 108.8 . . ?
C7 C8 H8A 108.8 . . ?
O4 C8 H8B 108.8 . . ?
C7 C8 H8B 108.8 . . ?
H8A C8 H8B 107.7 . . ?
O2 C9 O4 119.2(2) . . ?
O2 C9 C10 123.1(3) . . ?
O4 C9 C10 117.6(2) . . ?
C11 C10 C6 120.2(2) . . ?
C11 C10 C9 118.1(2) . . ?
C6 C10 C9 121.6(2) . . ?
C10 C11 C12 120.2(2) . . ?
C10 C11 H11 119.9 . . ?
C12 C11 H11 119.9 . . ?
C11 C12 C4 120.3(2) . . ?
C11 C12 C1 118.5(2) . . ?
C4 C12 C1 121.1(2) . . ?
C18 C13 C14 117.2(3) . . ?
C18 C13 C3 123.2(2) . . ?
C14 C13 C3 119.6(2) . . ?
C15 C14 C13 121.4(3) . . ?
C15 C14 H14 119.3 . . ?
C13 C14 H14 119.3 . . ?
C14 C15 C16 120.7(3) . . ?
C14 C15 H15 119.7 . . ?
C16 C15 H15 119.7 . . ?
C15 C16 C17 118.8(3) . . ?
C15 C16 H16 120.6 . . ?
C17 C16 H16 120.6 . . ?
C18 C17 C16 120.4(3) . . ?
C18 C17 H17 119.8 . . ?
C16 C17 H17 119.8 . . ?
C17 C18 C13 121.4(3) . . ?
C17 C18 H18 119.3 . . ?
C13 C18 H18 119.3 . . ?
C3 C19 H19A 109.5 . . ?
C3 C19 H19B 109.5 . . ?
H19A C19 H19B 109.5 . . ?
C3 C19 H19C 109.5 . . ?
H19A C19 H19C 109.5 . . ?
H19B C19 H19C 109.5 . . ?
C25 C20 C21 117.8(3) . . ?
C25 C20 C7 122.7(2) . . ?
C21 C20 C7 119.5(2) . . ?
C22 C21 C20 121.6(3) . . ?
C22 C21 H21 119.2 . . ?
C20 C21 H21 119.2 . . ?
C21 C22 C23 120.0(3) . . ?
C21 C22 H22 120.0 . . ?
C23 C22 H22 120.0 . . ?
C24 C23 C22 119.2(3) . . ?
C24 C23 H23 120.4 . . ?
C22 C23 H23 120.4 . . ?
C23 C24 C25 121.3(3) . . ?
C23 C24 H24 119.4 . . ?
C25 C24 H24 119.4 . . ?
C24 C25 C20 120.2(3) . . ?
C24 C25 H25 119.9 . . ?
C20 C25 H25 119.9 . . ?
C7 C26 H26A 109.5 . . ?
C7 C26 H26B 109.5 . . ?
H26A C26 H26B 109.5 . . ?
C7 C26 H26C 109.5 . . ?
H26A C26 H26C 109.5 . . ?
H26B C26 H26C 109.5 . . ?

_diffrn_measured_fraction_theta_max 0.999
_diffrn_reflns_theta_full        25.97
_diffrn_measured_fraction_theta_full 0.999
_refine_diff_density_max         0.236
_refine_diff_density_min         -0.416
_refine_diff_density_rms         0.068