# Supplementary Material (ESI) for Organic and Biomolecular Chemistry
# This journal is © The Royal Society of Chemistry 2010

data_global
_journal_name_full               Org.Biomol.Chem.

_journal_coden_Cambridge         0177
_journal_volume                  ?
_journal_page_first              ?
_journal_year                    ?

_publ_contact_author_name        'Bu, Xianzhang'
_publ_contact_author_email       phsbxzh@mail.sysu.edu.cn

_publ_section_title              
;
New Fluorescent trans-DihydroFluoren-3-ones
from Aldol - Robinson Annulation Regioselective Addition
Involved One-Pot Reaction
;
loop_
_publ_author_name
'Yingpeng Huo'
'Xu Qiu'
'Weiyan Shao'
'Jianing Huang'
'Yanjun Yu'
;
Yinglin Zuo
;
'Linkun An'
'Jun Du'
'Xianzhang Bu'

# Attachment '- cif file of compound 2b.cif'

data_hyp_no3_091021
_database_code_depnum_ccdc_archive 'CCDC 762211'
#TrackingRef '- cif file of compound 2b.cif'

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C19 H20 O4'
_chemical_formula_weight         312.35

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 '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 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_H-M   'P c a 21'
_symmetry_space_group_name_Hall  'P 2c -2ac'
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, z+1/2'
'x+1/2, -y, z'
'-x+1/2, y, z+1/2'

_cell_length_a                   17.8305(2)
_cell_length_b                   5.36310(10)
_cell_length_c                   16.2017(2)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_volume                     1549.32(4)
_cell_formula_units_Z            4
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    12637
_cell_measurement_theta_min      2.4728
_cell_measurement_theta_max      71.1341

_exptl_crystal_description       prism
_exptl_crystal_colour            green
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.15
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.339
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             664
_exptl_absorpt_coefficient_mu    0.758
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.82088
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_process_details   
;
'Fri Oct 23 12:31:28 2009'
;

_exptl_special_details           
;
?
;

_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     1.54178
_diffrn_radiation_type           CuK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Xcalibur, Onyx, Nova'
_diffrn_measurement_method       '\w scans'
_diffrn_detector_area_resol_mean 8.2417
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            12513
_diffrn_reflns_av_R_equivalents  0.0297
_diffrn_reflns_av_sigmaI/netI    0.0138
_diffrn_reflns_limit_h_min       -21
_diffrn_reflns_limit_h_max       21
_diffrn_reflns_limit_k_min       -5
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_theta_min         4.96
_diffrn_reflns_theta_max         71.28
_reflns_number_total             2896
_reflns_number_gt                2894
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       
;
'Fri Oct 23 12:31:28 2009'
;
_computing_cell_refinement       
;
'Fri Oct 23 12:31:28 2009'
;
_computing_data_reduction        
;
'Fri Oct 23 12:31:28 2009'
;
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    ?
_computing_publication_material  ?

_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^)+(0.0511P)^2^+0.2948P] 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_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.06(14)
_refine_ls_number_reflns         2896
_refine_ls_number_parameters     213
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0285
_refine_ls_R_factor_gt           0.0285
_refine_ls_wR_factor_ref         0.0768
_refine_ls_wR_factor_gt          0.0768
_refine_ls_goodness_of_fit_ref   1.029
_refine_ls_restrained_S_all      1.029
_refine_ls_shift/su_max          0.008
_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 -0.66580(6) -0.8447(2) -0.81732(7) 0.0315(2) Uani 1 1 d . . .
O2 O -0.71122(5) -0.54906(19) -0.69444(6) 0.0271(2) Uani 1 1 d . . .
O3 O -0.64577(7) -0.1458(3) -0.40042(7) 0.0440(3) Uani 1 1 d . . .
O4 O -0.75811(5) -0.16181(18) -0.56282(7) 0.0288(2) Uani 1 1 d . . .
C1 C -0.51316(7) 0.1113(3) -0.54285(9) 0.0249(3) Uani 1 1 d . . .
C2 C -0.55735(8) 0.0839(3) -0.47543(9) 0.0266(3) Uani 1 1 d . . .
H2A H -0.5514 0.1969 -0.4324 0.032 Uiso 1 1 calc R . .
C3 C -0.61365(8) -0.1110(3) -0.46604(9) 0.0276(3) Uani 1 1 d . . .
C4 C -0.63119(7) -0.2799(3) -0.53993(8) 0.0223(3) Uani 1 1 d . . .
H4A H -0.6062 -0.4406 -0.5314 0.027 Uiso 1 1 calc R . .
C4A C -0.60337(7) -0.1687(2) -0.62179(8) 0.0208(3) Uani 1 1 d . . .
H4AA H -0.6391 -0.0412 -0.6401 0.025 Uiso 1 1 calc R . .
C4B C -0.59127(7) -0.3512(2) -0.69101(8) 0.0216(3) Uani 1 1 d . . .
C5 C -0.63962(7) -0.5234(3) -0.72477(8) 0.0232(3) Uani 1 1 d . . .
C6 C -0.61406(8) -0.6797(3) -0.78849(9) 0.0250(3) Uani 1 1 d . . .
C7 C -0.54035(8) -0.6579(3) -0.81687(9) 0.0274(3) Uani 1 1 d . . .
H7A H -0.5234 -0.7630 -0.8585 0.033 Uiso 1 1 calc R . .
C8 C -0.49210(8) -0.4811(3) -0.78356(9) 0.0267(3) Uani 1 1 d . . .
H8A H -0.4432 -0.4668 -0.8031 0.032 Uiso 1 1 calc R . .
C8A C -0.51749(8) -0.3259(3) -0.72084(8) 0.0233(3) Uani 1 1 d . . .
C9 C -0.47905(8) -0.1331(3) -0.67287(9) 0.0247(3) Uani 1 1 d . . .
C9A C -0.52621(7) -0.0498(2) -0.61327(9) 0.0230(3) Uani 1 1 d . . .
C14 C -0.71653(8) -0.3226(3) -0.53828(9) 0.0242(3) Uani 1 1 d . . .
C15 C -0.74411(10) -0.5624(3) -0.50168(11) 0.0341(3) Uani 1 1 d . . .
H15A H -0.7979 -0.5672 -0.5043 0.051 Uiso 1 1 calc R . .
H15B H -0.7283 -0.5733 -0.4452 0.051 Uiso 1 1 calc R . .
H15C H -0.7238 -0.7003 -0.5322 0.051 Uiso 1 1 calc R . .
C16 C -0.76534(9) -0.4145(4) -0.74231(12) 0.0394(4) Uani 1 1 d . . .
H16A H -0.8143 -0.4378 -0.7189 0.059 Uiso 1 1 calc R . .
H16B H -0.7650 -0.4754 -0.7980 0.059 Uiso 1 1 calc R . .
H16C H -0.7530 -0.2403 -0.7421 0.059 Uiso 1 1 calc R . .
C17 C -0.64347(9) -1.0070(3) -0.88246(10) 0.0334(3) Uani 1 1 d . . .
H17A H -0.6846 -1.1135 -0.8971 0.050 Uiso 1 1 calc R . .
H17B H -0.6019 -1.1070 -0.8646 0.050 Uiso 1 1 calc R . .
H17C H -0.6288 -0.9100 -0.9296 0.050 Uiso 1 1 calc R . .
C18 C -0.39900(8) -0.0659(3) -0.69043(11) 0.0343(4) Uani 1 1 d . . .
H18A H -0.3832 0.0630 -0.6532 0.051 Uiso 1 1 calc R . .
H18B H -0.3947 -0.0073 -0.7462 0.051 Uiso 1 1 calc R . .
H18C H -0.3679 -0.2102 -0.6831 0.051 Uiso 1 1 calc R . .
C19 C -0.45200(8) 0.3039(3) -0.54280(10) 0.0305(3) Uani 1 1 d . . .
H19A H -0.4522 0.3913 -0.4911 0.046 Uiso 1 1 calc R . .
H19B H -0.4603 0.4200 -0.5870 0.046 Uiso 1 1 calc R . .
H19C H -0.4044 0.2236 -0.5503 0.046 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 0.0335(5) 0.0303(5) 0.0308(5) -0.0092(4) 0.0004(5) -0.0020(4)
O2 0.0215(5) 0.0300(5) 0.0297(5) -0.0026(4) 0.0024(4) -0.0026(4)
O3 0.0483(7) 0.0601(8) 0.0236(6) -0.0061(5) 0.0066(5) -0.0176(6)
O4 0.0239(5) 0.0282(5) 0.0342(6) -0.0022(4) 0.0014(4) 0.0032(4)
C1 0.0219(6) 0.0219(6) 0.0310(7) 0.0038(6) -0.0066(6) 0.0023(5)
C2 0.0281(7) 0.0266(7) 0.0250(6) -0.0045(5) -0.0045(6) 0.0014(6)
C3 0.0261(7) 0.0311(7) 0.0256(7) -0.0016(6) -0.0008(6) 0.0016(6)
C4 0.0229(6) 0.0215(6) 0.0225(6) 0.0005(5) 0.0003(5) 0.0015(5)
C4A 0.0204(6) 0.0199(6) 0.0222(7) 0.0010(5) -0.0017(5) 0.0005(5)
C4B 0.0232(6) 0.0215(6) 0.0200(6) 0.0013(5) 0.0007(5) 0.0025(5)
C5 0.0235(7) 0.0235(7) 0.0226(7) 0.0003(5) 0.0004(5) 0.0014(5)
C6 0.0291(7) 0.0233(7) 0.0226(7) 0.0010(5) -0.0024(5) 0.0021(5)
C7 0.0328(7) 0.0276(7) 0.0216(7) 0.0009(6) 0.0038(6) 0.0065(6)
C8 0.0236(6) 0.0311(7) 0.0255(7) 0.0043(6) 0.0047(5) 0.0041(6)
C8A 0.0231(6) 0.0255(7) 0.0214(6) 0.0036(5) 0.0009(5) 0.0023(5)
C9 0.0245(7) 0.0239(6) 0.0257(7) 0.0048(6) -0.0023(5) 0.0005(5)
C9A 0.0220(6) 0.0212(6) 0.0258(7) 0.0040(5) -0.0015(5) 0.0004(5)
C14 0.0248(6) 0.0249(7) 0.0229(6) -0.0048(5) 0.0040(5) 0.0005(5)
C15 0.0329(8) 0.0288(8) 0.0407(8) 0.0017(7) 0.0067(6) -0.0055(6)
C16 0.0262(8) 0.0482(10) 0.0437(10) -0.0031(8) -0.0034(7) 0.0048(7)
C17 0.0413(8) 0.0303(8) 0.0286(7) -0.0074(6) -0.0028(6) 0.0050(7)
C18 0.0257(7) 0.0382(9) 0.0389(9) -0.0033(7) 0.0048(6) -0.0044(6)
C19 0.0305(7) 0.0258(7) 0.0352(8) 0.0017(6) -0.0066(6) -0.0040(6)

_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 C6 1.3610(18) . ?
O1 C17 1.4248(19) . ?
O2 C5 1.3748(16) . ?
O2 C16 1.433(2) . ?
O3 C3 1.222(2) . ?
O4 C14 1.2048(17) . ?
C1 C2 1.355(2) . ?
C1 C9A 1.450(2) . ?
C1 C19 1.5023(19) . ?
C2 C3 1.458(2) . ?
C2 H2A 0.9300 . ?
C3 C4 1.533(2) . ?
C4 C4A 1.5364(18) . ?
C4 C14 1.5389(18) . ?
C4 H4A 0.9800 . ?
C4A C4B 1.5042(19) . ?
C4A C9A 1.5228(18) . ?
C4A H4AA 0.9800 . ?
C4B C5 1.377(2) . ?
C4B C8A 1.4079(19) . ?
C5 C6 1.4061(19) . ?
C6 C7 1.397(2) . ?
C7 C8 1.390(2) . ?
C7 H7A 0.9300 . ?
C8 C8A 1.389(2) . ?
C8 H8A 0.9300 . ?
C8A C9 1.464(2) . ?
C9 C9A 1.356(2) . ?
C9 C18 1.4993(19) . ?
C14 C15 1.499(2) . ?
C15 H15A 0.9600 . ?
C15 H15B 0.9600 . ?
C15 H15C 0.9600 . ?
C16 H16A 0.9600 . ?
C16 H16B 0.9600 . ?
C16 H16C 0.9600 . ?
C17 H17A 0.9600 . ?
C17 H17B 0.9600 . ?
C17 H17C 0.9600 . ?
C18 H18A 0.9600 . ?
C18 H18B 0.9600 . ?
C18 H18C 0.9600 . ?
C19 H19A 0.9600 . ?
C19 H19B 0.9600 . ?
C19 H19C 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
C6 O1 C17 117.52(12) . . ?
C5 O2 C16 112.42(11) . . ?
C2 C1 C9A 118.47(13) . . ?
C2 C1 C19 119.74(14) . . ?
C9A C1 C19 121.78(13) . . ?
C1 C2 C3 124.21(14) . . ?
C1 C2 H2A 117.9 . . ?
C3 C2 H2A 117.9 . . ?
O3 C3 C2 121.53(14) . . ?
O3 C3 C4 119.58(14) . . ?
C2 C3 C4 118.87(13) . . ?
C3 C4 C4A 112.27(11) . . ?
C3 C4 C14 106.03(11) . . ?
C4A C4 C14 113.07(11) . . ?
C3 C4 H4A 108.4 . . ?
C4A C4 H4A 108.4 . . ?
C14 C4 H4A 108.4 . . ?
C4B C4A C9A 102.15(11) . . ?
C4B C4A C4 115.94(11) . . ?
C9A C4A C4 112.09(11) . . ?
C4B C4A H4AA 108.8 . . ?
C9A C4A H4AA 108.8 . . ?
C4 C4A H4AA 108.8 . . ?
C5 C4B C8A 120.89(13) . . ?
C5 C4B C4A 130.00(12) . . ?
C8A C4B C4A 109.11(12) . . ?
O2 C5 C4B 120.46(12) . . ?
O2 C5 C6 120.24(12) . . ?
C4B C5 C6 119.26(12) . . ?
O1 C6 C7 125.39(13) . . ?
O1 C6 C5 114.84(12) . . ?
C7 C6 C5 119.77(13) . . ?
C8 C7 C6 120.78(13) . . ?
C8 C7 H7A 119.6 . . ?
C6 C7 H7A 119.6 . . ?
C8A C8 C7 119.41(13) . . ?
C8A C8 H8A 120.3 . . ?
C7 C8 H8A 120.3 . . ?
C8 C8A C4B 119.86(13) . . ?
C8 C8A C9 131.21(13) . . ?
C4B C8A C9 108.86(12) . . ?
C9A C9 C8A 108.68(12) . . ?
C9A C9 C18 130.25(14) . . ?
C8A C9 C18 120.99(13) . . ?
C9 C9A C1 131.08(13) . . ?
C9 C9A C4A 110.96(12) . . ?
C1 C9A C4A 117.77(12) . . ?
O4 C14 C15 122.86(13) . . ?
O4 C14 C4 119.75(12) . . ?
C15 C14 C4 117.32(12) . . ?
C14 C15 H15A 109.5 . . ?
C14 C15 H15B 109.5 . . ?
H15A C15 H15B 109.5 . . ?
C14 C15 H15C 109.5 . . ?
H15A C15 H15C 109.5 . . ?
H15B C15 H15C 109.5 . . ?
O2 C16 H16A 109.5 . . ?
O2 C16 H16B 109.5 . . ?
H16A C16 H16B 109.5 . . ?
O2 C16 H16C 109.5 . . ?
H16A C16 H16C 109.5 . . ?
H16B C16 H16C 109.5 . . ?
O1 C17 H17A 109.5 . . ?
O1 C17 H17B 109.5 . . ?
H17A C17 H17B 109.5 . . ?
O1 C17 H17C 109.5 . . ?
H17A C17 H17C 109.5 . . ?
H17B C17 H17C 109.5 . . ?
C9 C18 H18A 109.5 . . ?
C9 C18 H18B 109.5 . . ?
H18A C18 H18B 109.5 . . ?
C9 C18 H18C 109.5 . . ?
H18A C18 H18C 109.5 . . ?
H18B C18 H18C 109.5 . . ?
C1 C19 H19A 109.5 . . ?
C1 C19 H19B 109.5 . . ?
H19A C19 H19B 109.5 . . ?
C1 C19 H19C 109.5 . . ?
H19A C19 H19C 109.5 . . ?
H19B C19 H19C 109.5 . . ?

_diffrn_measured_fraction_theta_max 0.987
_diffrn_reflns_theta_full        71.28
_diffrn_measured_fraction_theta_full 0.987
_refine_diff_density_max         0.175
_refine_diff_density_min         -0.153
_refine_diff_density_rms         0.035