#------------------------------------------------------------------------------
#$Date: 2016-03-21 04:24:29 +0200 (Mon, 21 Mar 2016) $
#$Revision: 178468 $
#$URL: svn://www.crystallography.net/cod/cif/4/02/89/4028961.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/. The original data for this entry
# were provided the Crystal Eye server at
# http://wwmm.ch.cam.ac.uk/crystaleye/, created by Nick Day at the
# Peter Murray-Rust laboratory.
#
# The file may be used within the scientific community so long as
# proper attribution is given to the journal article from which the
# data were obtained.
#
data_4028961
loop_
_publ_author_name
'Sánchez-Larios, Eduardo'
'Gravel, Michel'
_publ_section_title
;
 Diastereoselective Synthesis of Indanes via a Domino
 Stetter−Michael Reaction
;
_journal_issue                   19
_journal_name_full               'The Journal of Organic Chemistry'
_journal_page_first              7536
_journal_page_last               7539
_journal_paper_doi               10.1021/jo901468h
_journal_volume                  74
_journal_year                    2009
_chemical_formula_moiety         'C31 H24 O3'
_chemical_formula_sum            'C31 H24 O3'
_chemical_formula_weight         444.50
_chemical_name_systematic
; 
 ? 
;
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 1 21/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           'manual editing of SHELXL template'
_cell_angle_alpha                90.00
_cell_angle_beta                 99.333(2)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   11.6926(4)
_cell_length_b                   17.3098(6)
_cell_length_c                   11.6041(4)
_cell_measurement_reflns_used    128
_cell_measurement_temperature    173(2)
_cell_measurement_theta_max      29.39
_cell_measurement_theta_min      4.53
_cell_volume                     2317.54(14)
_computing_cell_refinement
'Saint and SADABS (Apex2, v2009.3-0, Bruker AXS)'
_computing_data_collection       'Apex2 (v2009.3-0, Bruker AXS)'
_computing_data_reduction
'Saint and SADABS (Apex2, v2009.3-0, Bruker AXS)'
_computing_molecular_graphics
' Cameron (WinGX v1.80.03 2008), Ortep (SHELXTL-NT v6.14, Bruker AXS)'
_computing_publication_material  'WinGX v1.80.03 2008 (L. J. Farrugia)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution
' SIR-2004 (A. Altomare, G. Cascarano, C. Giacovazzo et al., 1999)'
_diffrn_ambient_temperature      173(2)
_diffrn_measured_fraction_theta_full 0.993
_diffrn_measured_fraction_theta_max 0.993
_diffrn_measurement_device       '62mm 4K CCD camera on D85 goniostat'
_diffrn_measurement_device_type  'Proteum R Smart 6000 (Bruker AXS)'
_diffrn_measurement_method       'CCD rotation images, φ and ω scans'
_diffrn_radiation_monochromator  'Montel200 multilayer graded optics'
_diffrn_radiation_source         'Bruker AXS FR591, fine-focus rotating anode'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0590
_diffrn_reflns_av_sigmaI/netI    0.0539
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       19
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            14979
_diffrn_reflns_theta_full        62.37
_diffrn_reflns_theta_max         62.37
_diffrn_reflns_theta_min         3.83
_exptl_absorpt_coefficient_mu    0.641
_exptl_absorpt_correction_T_max  0.9644
_exptl_absorpt_correction_T_min  0.9111
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS (Apex2, Bruker AXS)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.274
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       'thin plate'
_exptl_crystal_F_000             936
_exptl_crystal_size_max          0.15
_exptl_crystal_size_mid          0.07
_exptl_crystal_size_min          0.06
_refine_diff_density_max         0.202
_refine_diff_density_min         -0.227
_refine_diff_density_rms         0.049
_refine_ls_extinction_coef       0.0064(7)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_ref   1.022
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     328
_refine_ls_number_reflns         3660
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.022
_refine_ls_R_factor_all          0.0685
_refine_ls_R_factor_gt           0.0545
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.1035P)²+0.2296P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1469
_refine_ls_wR_factor_ref         0.1627
_reflns_number_gt                2828
_reflns_number_total             3660
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jo901468hsup1.cif
_cod_data_source_block           es1361
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               4028961
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'
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
O8"' O 0.13182(14) 0.42644(10) 0.28264(13) 0.0637(5) Uani 1 1 d
O8" O 0.26909(15) 0.29585(10) 0.55949(13) 0.0617(5) Uani 1 1 d
O9' O 0.59420(13) 0.21233(9) 0.24942(13) 0.0540(4) Uani 1 1 d
C1 C 0.41648(17) 0.29788(12) 0.31705(18) 0.0433(5) Uani 1 1 d
H1 H 0.3974(18) 0.2617(13) 0.2544(19) 0.045(6) Uiso 1 1 d
C1' C 0.51352(19) 0.26473(14) 0.40830(18) 0.0460(5) Uani 1 1 d
H1A' H 0.546(2) 0.3041(13) 0.466(2) 0.057(7) Uiso 1 1 d
H1B' H 0.4882(19) 0.2224(13) 0.4542(19) 0.051(6) Uiso 1 1 d
C1" C 0.27223(17) 0.26945(13) 0.46229(17) 0.0454(5) Uani 1 1 d
C1"' C 0.19939(18) 0.44855(13) 0.36710(18) 0.0473(5) Uani 1 1 d
C2 C 0.30493(17) 0.32066(13) 0.36654(17) 0.0428(5) Uani 1 1 d
H2 H 0.2414(18) 0.3189(11) 0.3001(17) 0.040(5) Uiso 1 1 d
C2' C 0.60902(18) 0.22664(12) 0.35405(18) 0.0446(5) Uani 1 1 d
C2" C 0.24200(16) 0.18721(13) 0.43545(16) 0.0433(5) Uani 1 1 d
C2"' C 0.17008(17) 0.51566(12) 0.43716(17) 0.0440(5) Uani 1 1 d
C3 C 0.31583(18) 0.40629(13) 0.39889(19) 0.0452(5) Uani 1 1 d
H3 H 0.3480(18) 0.4134(11) 0.4828(18) 0.044(6) Uiso 1 1 d
C3' C 0.71942(18) 0.20440(12) 0.43011(18) 0.0460(5) Uani 1 1 d
C3" C 0.22469(18) 0.15819(13) 0.32178(17) 0.0471(5) Uani 1 1 d
H3" H 0.2326 0.1914 0.2584 0.056 Uiso 1 1 calc
C3"' C 0.06702(19) 0.55497(14) 0.39531(18) 0.0511(6) Uani 1 1 d
H3"' H 0.0226 0.5406 0.3225 0.061 Uiso 1 1 calc
C4 C 0.39997(17) 0.43602(13) 0.32172(19) 0.0475(5) Uani 1 1 d
C4' C 0.80138(19) 0.16229(14) 0.3807(2) 0.0545(6) Uani 1 1 d
H4' H 0.7847 0.1472 0.3011 0.065 Uiso 1 1 calc
C4" C 0.19617(19) 0.08150(14) 0.30081(19) 0.0526(6) Uani 1 1 d
H4" H 0.1850 0.0622 0.2232 0.063 Uiso 1 1 calc
C4"' C 0.0296(2) 0.61434(14) 0.4589(2) 0.0556(6) Uani 1 1 d
H4"' H -0.0403 0.6409 0.4298 0.067 Uiso 1 1 calc
C5 C 0.4242(2) 0.51185(14) 0.2960(2) 0.0619(6) Uani 1 1 d
H5 H 0.3913 0.5536 0.3326 0.074 Uiso 1 1 calc
C5' C 0.9061(2) 0.14251(15) 0.4468(2) 0.0628(7) Uani 1 1 d
H5' H 0.9616 0.1142 0.4124 0.075 Uiso 1 1 calc
C5" C 0.1838(2) 0.03267(13) 0.3922(2) 0.0553(6) Uani 1 1 d
H5" H 0.1637 -0.0200 0.3772 0.066 Uiso 1 1 calc
C5"' C 0.0935(2) 0.63522(13) 0.5646(2) 0.0560(6) Uani 1 1 d
H5"' H 0.0667 0.6754 0.6091 0.067 Uiso 1 1 calc
C6 C 0.4979(2) 0.52543(15) 0.2150(3) 0.0701(7) Uani 1 1 d
H6 H 0.5159 0.5770 0.1965 0.084 Uiso 1 1 calc
C6' C 0.9306(2) 0.16381(16) 0.5631(2) 0.0635(7) Uani 1 1 d
H6' H 1.0027 0.1500 0.6087 0.076 Uiso 1 1 calc
C6" C 0.2009(2) 0.06041(14) 0.5053(2) 0.0559(6) Uani 1 1 d
H6" H 0.1926 0.0269 0.5682 0.067 Uiso 1 1 calc
C6"' C 0.1960(2) 0.59811(14) 0.60595(19) 0.0545(6) Uani 1 1 d
H6"' H 0.2401 0.6131 0.6786 0.065 Uiso 1 1 calc
C7 C 0.5452(2) 0.46459(16) 0.1612(2) 0.0629(7) Uani 1 1 d
H7 H 0.5929 0.4749 0.1040 0.075 Uiso 1 1 calc
C7' C 0.8500(2) 0.20520(14) 0.6131(2) 0.0591(6) Uani 1 1 d
H7' H 0.8669 0.2197 0.6930 0.071 Uiso 1 1 calc
C7" C 0.22984(18) 0.13692(14) 0.52657(18) 0.0507(6) Uani 1 1 d
H7" H 0.2417 0.1557 0.6045 0.061 Uiso 1 1 calc
C7"' C 0.23512(18) 0.53875(13) 0.54190(18) 0.0477(5) Uani 1 1 d
H7"' H 0.3067 0.5140 0.5700 0.057 Uiso 1 1 calc
C8 C 0.52386(18) 0.38896(14) 0.18992(19) 0.0514(6) Uani 1 1 d
H8 H 0.5583 0.3474 0.1546 0.062 Uiso 1 1 calc
C8' C 0.74470(19) 0.22566(14) 0.54693(19) 0.0519(6) Uani 1 1 d
H8' H 0.6898 0.2543 0.5816 0.062 Uiso 1 1 calc
C9 C 0.45087(17) 0.37464(12) 0.27155(17) 0.0444(5) Uani 1 1 d
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'
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
C9 C1 C1' 111.24(17)
C9 C1 C2 101.11(17)
C1' C1 C2 114.22(16)
C9 C1 H1 110.7(13)
C1' C1 H1 109.5(13)
C2 C1 H1 109.8(13)
C2' C1' C1 112.83(17)
C2' C1' H1A' 110.6(14)
C1 C1' H1A' 112.0(14)
C2' C1' H1B' 102.0(13)
C1 C1' H1B' 113.6(13)
H1A' C1' H1B' 105.2(18)
O8" C1" C2" 120.60(19)
O8" C1" C2 120.4(2)
C2" C1" C2 119.02(17)
O8"' C1"' C2"' 120.54(19)
O8"' C1"' C3 118.55(19)
C2"' C1"' C3 120.90(18)
C1" C2 C3 114.03(17)
C1" C2 C1 116.56(17)
C3 C2 C1 107.11(17)
C1" C2 H2 108.0(12)
C3 C2 H2 104.2(12)
C1 C2 H2 105.9(11)
O9' C2' C3' 120.31(19)
O9' C2' C1' 120.26(19)
C3' C2' C1' 119.40(18)
C7" C2" C3" 118.4(2)
C7" C2" C1" 119.25(18)
C3" C2" C1" 122.38(18)
C7"' C2"' C3"' 118.9(2)
C7"' C2"' C1"' 124.22(19)
C3"' C2"' C1"' 116.81(19)
C4 C3 C2 102.66(16)
C4 C3 C1"' 109.24(17)
C2 C3 C1"' 111.54(18)
C4 C3 H3 110.9(12)
C2 C3 H3 111.3(12)
C1"' C3 H3 110.9(12)
C8' C3' C4' 119.1(2)
C8' C3' C2' 122.40(19)
C4' C3' C2' 118.49(19)
C4" C3" C2" 120.44(19)
C4" C3" H3" 119.8
C2" C3" H3" 119.8
C4"' C3"' C2"' 120.5(2)
C4"' C3"' H3"' 119.8
C2"' C3"' H3"' 119.8
C5 C4 C9 121.2(2)
C5 C4 C3 128.4(2)
C9 C4 C3 110.42(19)
C5' C4' C3' 120.5(2)
C5' C4' H4' 119.7
C3' C4' H4' 119.7
C3" C4" C5" 120.4(2)
C3" C4" H4" 119.8
C5" C4" H4" 119.8
C3"' C4"' C5"' 119.9(2)
C3"' C4"' H4"' 120.0
C5"' C4"' H4"' 120.0
C4 C5 C6 118.4(2)
C4 C5 H5 120.8
C6 C5 H5 120.8
C4' C5' C6' 120.0(2)
C4' C5' H5' 120.0
C6' C5' H5' 120.0
C4" C5" C6" 120.0(2)
C4" C5" H5" 120.0
C6" C5" H5" 120.0
C6"' C5"' C4"' 120.3(2)
C6"' C5"' H5"' 119.9
C4"' C5"' H5"' 119.9
C7 C6 C5 120.8(2)
C7 C6 H6 119.6
C5 C6 H6 119.6
C7' C6' C5' 120.0(2)
C7' C6' H6' 120.0
C5' C6' H6' 120.0
C7" C6" C5" 119.8(2)
C7" C6" H6" 120.1
C5" C6" H6" 120.1
C5"' C6"' C7"' 120.2(2)
C5"' C6"' H6"' 119.9
C7"' C6"' H6"' 119.9
C8 C7 C6 120.7(2)
C8 C7 H7 119.7
C6 C7 H7 119.7
C6' C7' C8' 120.3(2)
C6' C7' H7' 119.9
C8' C7' H7' 119.9
C6" C7" C2" 121.1(2)
C6" C7" H7" 119.5
C2" C7" H7" 119.5
C2"' C7"' C6"' 120.1(2)
C2"' C7"' H7"' 119.9
C6"' C7"' H7"' 119.9
C7 C8 C9 119.1(2)
C7 C8 H8 120.5
C9 C8 H8 120.5
C7' C8' C3' 120.1(2)
C7' C8' H8' 119.9
C3' C8' H8' 119.9
C4 C9 C8 119.9(2)
C4 C9 C1 111.72(18)
C8 C9 C1 128.4(2)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
O8"' C1"' 1.217(3)
O8" C1" 1.223(2)
O9' C2' 1.224(2)
C1 C9 1.508(3)
C1 C1' 1.532(3)
C1 C2 1.559(3)
C1 H1 0.96(2)
C1' C2' 1.518(3)
C1' H1A' 0.99(2)
C1' H1B' 0.98(2)
C1" C2" 1.488(3)
C1" C2 1.518(3)
C1"' C2"' 1.489(3)
C1"' C3 1.537(3)
C2 C3 1.529(3)
C2 H2 0.98(2)
C2' C3' 1.491(3)
C2" C7" 1.395(3)
C2" C3" 1.395(3)
C2"' C7"' 1.384(3)
C2"' C3"' 1.400(3)
C3 C4 1.523(3)
C3 H3 0.99(2)
C3' C8' 1.389(3)
C3' C4' 1.399(3)
C3" C4" 1.381(3)
C3" H3" 0.9500
C3"' C4"' 1.377(3)
C3"' H3"' 0.9500
C4 C5 1.386(3)
C4 C9 1.391(3)
C4' C5' 1.379(3)
C4' H4' 0.9500
C4" C5" 1.381(3)
C4" H4" 0.9500
C4"' C5"' 1.377(3)
C4"' H4"' 0.9500
C5 C6 1.395(3)
C5 H5 0.9500
C5' C6' 1.384(4)
C5' H5' 0.9500
C5" C6" 1.382(3)
C5" H5" 0.9500
C5"' C6"' 1.375(3)
C5"' H5"' 0.9500
C6 C7 1.385(4)
C6 H6 0.9500
C6' C7' 1.384(3)
C6' H6' 0.9500
C6" C7" 1.379(3)
C6" H6" 0.9500
C6"' C7"' 1.389(3)
C6"' H6"' 0.9500
C7 C8 1.384(3)
C7 H7 0.9500
C7' C8' 1.387(3)
C7' H7' 0.9500
C7" H7" 0.9500
C7"' H7"' 0.9500
C8 C9 1.396(3)
C8 H8 0.9500
C8' H8' 0.9500
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
C9 C1 C1' C2' -79.3(2)
C2 C1 C1' C2' 166.99(18)
O8" C1" C2 C3 -7.8(3)
C2" C1" C2 C3 171.04(17)
O8" C1" C2 C1 117.8(2)
C2" C1" C2 C1 -63.3(2)
C9 C1 C2 C1" -155.34(17)
C1' C1 C2 C1" -35.8(3)
C9 C1 C2 C3 -26.3(2)
C1' C1 C2 C3 93.3(2)
C1 C1' C2' O9' -13.2(3)
C1 C1' C2' C3' 168.93(18)
O8" C1" C2" C7" -11.2(3)
C2 C1" C2" C7" 169.93(18)
O8" C1" C2" C3" 168.5(2)
C2 C1" C2" C3" -10.3(3)
O8"' C1"' C2"' C7"' 171.9(2)
C3 C1"' C2"' C7"' -8.7(3)
O8"' C1"' C2"' C3"' -5.2(3)
C3 C1"' C2"' C3"' 174.18(18)
C1" C2 C3 C4 154.11(17)
C1 C2 C3 C4 23.6(2)
C1" C2 C3 C1"' -89.0(2)
C1 C2 C3 C1"' 140.46(17)
O8"' C1"' C3 C4 81.1(3)
C2"' C1"' C3 C4 -98.2(2)
O8"' C1"' C3 C2 -31.7(3)
C2"' C1"' C3 C2 148.98(19)
O9' C2' C3' C8' 173.9(2)
C1' C2' C3' C8' -8.2(3)
O9' C2' C3' C4' -4.4(3)
C1' C2' C3' C4' 173.5(2)
C7" C2" C3" C4" 0.0(3)
C1" C2" C3" C4" -179.68(19)
C7"' C2"' C3"' C4"' -1.6(3)
C1"' C2"' C3"' C4"' 175.6(2)
C2 C3 C4 C5 165.6(2)
C1"' C3 C4 C5 47.1(3)
C2 C3 C4 C9 -11.7(2)
C1"' C3 C4 C9 -130.17(19)
C8' C3' C4' C5' -0.4(3)
C2' C3' C4' C5' 178.0(2)
C2" C3" C4" C5" 0.3(3)
C2"' C3"' C4"' C5"' -0.2(4)
C9 C4 C5 C6 2.2(4)
C3 C4 C5 C6 -174.8(2)
C3' C4' C5' C6' 0.5(4)
C3" C4" C5" C6" -0.4(3)
C3"' C4"' C5"' C6"' 1.4(4)
C4 C5 C6 C7 0.4(4)
C4' C5' C6' C7' -0.2(4)
C4" C5" C6" C7" 0.2(3)
C4"' C5"' C6"' C7"' -0.6(4)
C5 C6 C7 C8 -2.5(4)
C5' C6' C7' C8' -0.2(4)
C5" C6" C7" C2" 0.2(3)
C3" C2" C7" C6" -0.3(3)
C1" C2" C7" C6" 179.4(2)
C3"' C2"' C7"' C6"' 2.4(3)
C1"' C2"' C7"' C6"' -174.7(2)
C5"' C6"' C7"' C2"' -1.2(3)
C6 C7 C8 C9 1.9(4)
C6' C7' C8' C3' 0.2(4)
C4' C3' C8' C7' 0.0(3)
C2' C3' C8' C7' -178.3(2)
C5 C4 C9 C8 -2.8(3)
C3 C4 C9 C8 174.76(19)
C5 C4 C9 C1 177.1(2)
C3 C4 C9 C1 -5.4(2)
C7 C8 C9 C4 0.7(3)
C7 C8 C9 C1 -179.2(2)
C1' C1 C9 C4 -102.1(2)
C2 C1 C9 C4 19.5(2)
C1' C1 C9 C8 77.7(3)
C2 C1 C9 C8 -160.6(2)
