#------------------------------------------------------------------------------
#$Date: 2016-02-20 18:35:30 +0200 (Sat, 20 Feb 2016) $
#$Revision: 176787 $
#$URL: svn://www.crystallography.net/cod/cif/2/21/20/2212006.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/. The original data for this entry
# were provided by IUCr Journals, http://journals.iucr.org/.
#
# 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_2212006
loop_
_publ_author_name
'D. Gayathri'
'D. Velmurugan'
'K. Ravikumar'
'G. Savitha'
'P. T. Perumal'
_publ_section_title
3-(3-Methoxybenzoyl)-1',6,6-trimethyl-4,5,6,7-tetrahydrospiro[benzo[b]furan-2(3H),3'(2'H)-1H-indole]-4,2'-dione
_journal_coeditor_code           AT2209
_journal_issue                   2
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o846
_journal_page_last               o848
_journal_paper_doi               10.1107/S1600536807002590
_journal_volume                  63
_journal_year                    2007
_chemical_formula_iupac          'C26 H25 N O5'
_chemical_formula_moiety         'C26 H25 N O5'
_chemical_formula_sum            'C26 H25 N O5'
_chemical_formula_weight         431.47
_chemical_name_systematic
;
3-(3-Methoxybenzoyl)-1',6,6-trimethyl-4,5,6,7-
tetrahydrospiro[benzo[b]furan-2(3H),3'(2'H)-1H-indole]-4,2'-dione
;
_space_group_IT_number           2
_symmetry_cell_setting           triclinic
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                116.1680(10)
_cell_angle_beta                 93.0050(10)
_cell_angle_gamma                111.9250(10)
_cell_formula_units_Z            2
_cell_length_a                   9.4557(8)
_cell_length_b                   11.7500(10)
_cell_length_c                   12.3946(10)
_cell_measurement_reflns_used    2164
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      25.00
_cell_measurement_theta_min      1.90
_cell_volume                     1106.90(16)
_computing_cell_refinement       'SAINT (Bruker, 2001)'
_computing_data_collection       'SMART (Bruker, 2001)'
_computing_data_reduction        SAINT
_computing_molecular_graphics    'PLATON (Spek, 2003)'
_computing_publication_material  'SHELXL97 and PARST (Nardelli, 1995)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 1997)'
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.945
_diffrn_measurement_device       'Bruker SMART APEX'
_diffrn_measurement_device_type  'Bruker SMART APEX CCD area-detector'
_diffrn_measurement_method       ω
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0167
_diffrn_reflns_av_sigmaI/netI    0.0189
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            12751
_diffrn_reflns_theta_full        25.00
_diffrn_reflns_theta_max         28.00
_diffrn_reflns_theta_min         1.90
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.090
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            white
_exptl_crystal_density_diffrn    1.295
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             456
_exptl_crystal_size_max          0.26
_exptl_crystal_size_mid          0.24
_exptl_crystal_size_min          0.23
_refine_diff_density_max         0.257
_refine_diff_density_min         -0.183
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.034
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     291
_refine_ls_number_reflns         5046
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.034
_refine_ls_R_factor_all          0.0498
_refine_ls_R_factor_gt           0.0441
_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)+(0.0669P)²+0.2028P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1183
_refine_ls_wR_factor_ref         0.1235
_reflns_number_gt                4353
_reflns_number_total             5046
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            at2209.cif
_cod_data_source_block           I
_cod_database_code               2212006
_cod_database_fobs_code          2212006
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'
loop_
_atom_site_type_symbol
_atom_site_label
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_occupancy
C C1 0.72244(13) 0.89049(12) 0.28428(10) 0.0341(2) Uani d . 1
C C2 0.74922(13) 0.77209(12) 0.29653(10) 0.0333(2) Uani d . 1
H H2 0.8454 0.8147 0.3620 0.040 Uiso calc R 1
C C3 0.60670(14) 0.71230(12) 0.33728(11) 0.0365(3) Uani d . 1
C C4 0.52439(14) 0.78674(12) 0.35575(11) 0.0365(2) Uani d . 1
C C5 0.86404(14) 1.03666(12) 0.36702(11) 0.0385(3) Uani d . 1
C C6 0.82736(14) 0.99884(12) 0.16860(11) 0.0380(3) Uani d . 1
C C7 0.84378(19) 1.01798(16) 0.06723(14) 0.0532(3) Uani d . 1
H H7 0.9254 1.0977 0.0740 0.064 Uiso calc R 1
C C8 0.7333(2) 0.91318(19) -0.04543(14) 0.0615(4) Uani d . 1
H H8 0.7411 0.9235 -0.1154 0.074 Uiso calc R 1
C C9 0.61269(19) 0.79465(17) -0.05659(13) 0.0571(4) Uani d . 1
H H9 0.5412 0.7259 -0.1336 0.069 Uiso calc R 1
C C10 0.59696(16) 0.77688(14) 0.04678(12) 0.0451(3) Uani d . 1
H H10 0.5151 0.6973 0.0401 0.054 Uiso calc R 1
C C11 0.70543(14) 0.87978(12) 0.15882(11) 0.0352(2) Uani d . 1
C C12 1.06119(17) 1.22065(15) 0.33499(16) 0.0589(4) Uani d . 1
H H12A 1.1004 1.2664 0.4237 0.088 Uiso calc R 1
H H12B 1.0352 1.2813 0.3141 0.088 Uiso calc R 1
H H12C 1.1407 1.2016 0.2956 0.088 Uiso calc R 1
C C13 0.75897(14) 0.66445(12) 0.17428(11) 0.0352(2) Uani d . 1
C C14 0.90945(14) 0.70331(12) 0.13613(11) 0.0364(2) Uani d . 1
C C15 1.05414(15) 0.80499(15) 0.22207(12) 0.0458(3) Uani d . 1
H H15 1.0597 0.8546 0.3062 0.055 Uiso calc R 1
C C16 1.18931(16) 0.83111(17) 0.18062(14) 0.0536(3) Uani d . 1
H H16 1.2866 0.8969 0.2380 0.064 Uiso calc R 1
C C17 1.18283(17) 0.76136(17) 0.05567(14) 0.0518(3) Uani d . 1
H H17 1.2748 0.7809 0.0292 0.062 Uiso calc R 1
C C18 1.03835(17) 0.66209(16) -0.02990(12) 0.0484(3) Uani d . 1
C C19 0.90216(16) 0.63238(15) 0.01059(12) 0.0444(3) Uani d . 1
H H19 0.8054 0.5645 -0.0467 0.053 Uiso calc R 1
C C20 1.1581(2) 0.6053(3) -0.19815(18) 0.0845(6) Uani d . 1
H H20A 1.2117 0.6990 -0.1860 0.127 Uiso calc R 1
H H20B 1.1300 0.5375 -0.2851 0.127 Uiso calc R 1
H H20C 1.2265 0.5894 -0.1523 0.127 Uiso calc R 1
C C21 0.56118(15) 0.59708(13) 0.36371(11) 0.0386(3) Uani d . 1
C C22 0.40235(15) 0.55575(13) 0.39289(12) 0.0418(3) Uani d . 1
H H22A 0.3977 0.5050 0.4377 0.050 Uiso calc R 1
H H22B 0.3203 0.4918 0.3153 0.050 Uiso calc R 1
C C23 0.36813(15) 0.68183(13) 0.47064(12) 0.0403(3) Uani d . 1
C C24 0.38025(15) 0.76549(14) 0.40175(13) 0.0433(3) Uani d . 1
H H24A 0.2877 0.7141 0.3322 0.052 Uiso calc R 1
H H24B 0.3840 0.8565 0.4578 0.052 Uiso calc R 1
C C25 0.20137(19) 0.62649(17) 0.48636(17) 0.0604(4) Uani d . 1
H H25A 0.1269 0.5670 0.4060 0.091 Uiso calc R 1
H H25B 0.1791 0.7047 0.5351 0.091 Uiso calc R 1
H H25C 0.1931 0.5729 0.5279 0.091 Uiso calc R 1
C C26 0.4855(2) 0.77606(17) 0.59867(13) 0.0580(4) Uani d . 1
H H26A 0.5908 0.8113 0.5894 0.087 Uiso calc R 1
H H26B 0.4769 0.7222 0.6400 0.087 Uiso calc R 1
H H26C 0.4629 0.8540 0.6472 0.087 Uiso calc R 1
N N1 0.92108(12) 1.08882(10) 0.29206(10) 0.0413(2) Uani d . 1
O O1 0.58396(10) 0.89384(9) 0.33014(9) 0.0414(2) Uani d . 1
O O2 0.91499(13) 1.09244(10) 0.47810(8) 0.0575(3) Uani d . 1
O O3 0.64653(11) 0.55144(9) 0.10933(9) 0.0502(2) Uani d . 1
O O4 1.01890(14) 0.59033(16) -0.15526(10) 0.0749(4) Uani d . 1
O O5 0.64350(13) 0.53786(11) 0.36291(10) 0.0546(3) Uani d . 1
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'
N N 0.0061 0.0033 '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'
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_publ_flag
O1 C1 C11 110.89(9) ?
O1 C1 C5 108.10(9) ?
C11 C1 C5 102.69(9) ?
O1 C1 C2 106.05(8) ?
C11 C1 C2 117.77(9) ?
C5 C1 C2 111.08(9) ?
C3 C2 C13 113.55(9) ?
C3 C2 C1 100.78(9) ?
C13 C2 C1 111.98(9) ?
C3 C2 H2 110.1 ?
C13 C2 H2 110.1 ?
C1 C2 H2 110.1 ?
C4 C3 C21 121.18(11) ?
C4 C3 C2 110.51(10) ?
C21 C3 C2 128.18(10) ?
C3 C4 O1 114.41(10) ?
C3 C4 C24 127.07(11) ?
O1 C4 C24 118.52(10) ?
O2 C5 N1 126.76(12) ?
O2 C5 C1 125.63(11) ?
N1 C5 C1 107.60(10) ?
C7 C6 C11 121.54(12) ?
C7 C6 N1 128.42(12) ?
C11 C6 N1 110.04(10) ?
C6 C7 C8 117.17(13) ?
C6 C7 H7 121.4 ?
C8 C7 H7 121.4 ?
C9 C8 C7 121.91(13) ?
C9 C8 H8 119.0 ?
C7 C8 H8 119.0 ?
C8 C9 C10 120.35(13) ?
C8 C9 H9 119.8 ?
C10 C9 H9 119.8 ?
C11 C10 C9 118.34(13) ?
C11 C10 H10 120.8 ?
C9 C10 H10 120.8 ?
C10 C11 C6 120.68(11) ?
C10 C11 C1 131.15(11) ?
C6 C11 C1 108.16(10) ?
N1 C12 H12A 109.5 ?
N1 C12 H12B 109.5 ?
H12A C12 H12B 109.5 ?
N1 C12 H12C 109.5 ?
H12A C12 H12C 109.5 ?
H12B C12 H12C 109.5 ?
O3 C13 C14 121.17(11) ?
O3 C13 C2 120.37(10) ?
C14 C13 C2 118.45(10) ?
C19 C14 C15 119.97(11) ?
C19 C14 C13 117.78(11) ?
C15 C14 C13 122.24(11) ?
C16 C15 C14 119.04(12) ?
C16 C15 H15 120.5 ?
C14 C15 H15 120.5 ?
C17 C16 C15 121.28(13) ?
C17 C16 H16 119.4 ?
C15 C16 H16 119.4 ?
C16 C17 C18 119.54(12) ?
C16 C17 H17 120.2 ?
C18 C17 H17 120.2 ?
O4 C18 C17 124.06(12) ?
O4 C18 C19 116.11(13) ?
C17 C18 C19 119.83(12) ?
C18 C19 C14 120.31(12) ?
C18 C19 H19 119.8 ?
C14 C19 H19 119.8 ?
O4 C20 H20A 109.5 ?
O4 C20 H20B 109.5 ?
H20A C20 H20B 109.5 ?
O4 C20 H20C 109.5 ?
H20A C20 H20C 109.5 ?
H20B C20 H20C 109.5 ?
O5 C21 C3 123.17(11) ?
O5 C21 C22 122.43(11) ?
C3 C21 C22 114.41(10) ?
C21 C22 C23 113.83(10) ?
C21 C22 H22A 108.8 ?
C23 C22 H22A 108.8 ?
C21 C22 H22B 108.8 ?
C23 C22 H22B 108.8 ?
H22A C22 H22B 107.7 ?
C26 C23 C25 109.09(12) ?
C26 C23 C22 109.80(11) ?
C25 C23 C22 108.94(11) ?
C26 C23 C24 110.56(11) ?
C25 C23 C24 109.40(11) ?
C22 C23 C24 109.02(10) ?
C4 C24 C23 110.05(10) ?
C4 C24 H24A 109.7 ?
C23 C24 H24A 109.7 ?
C4 C24 H24B 109.7 ?
C23 C24 H24B 109.7 ?
H24A C24 H24B 108.2 ?
C23 C25 H25A 109.5 ?
C23 C25 H25B 109.5 ?
H25A C25 H25B 109.5 ?
C23 C25 H25C 109.5 ?
H25A C25 H25C 109.5 ?
H25B C25 H25C 109.5 ?
C23 C26 H26A 109.5 ?
C23 C26 H26B 109.5 ?
H26A C26 H26B 109.5 ?
C23 C26 H26C 109.5 ?
H26A C26 H26C 109.5 ?
H26B C26 H26C 109.5 ?
C5 N1 C6 111.30(10) y
C5 N1 C12 123.80(10) y
C6 N1 C12 124.90(10) y
C4 O1 C1 107.90(10) y
C18 O4 C20 117.20(10) y
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_publ_flag
C1 O1 1.4620(10) y
C1 C11 1.499(2) y
C1 C5 1.543(2) y
C1 C2 1.571(2) y
C2 C3 1.497(2) y
C2 C13 1.522(2) y
C2 H2 0.9800 ?
C3 C4 1.332(2) y
C3 C21 1.448(2) y
C4 O1 1.3580(10) y
C4 C24 1.483(2) y
C5 O2 1.207(2) y
C5 N1 1.356(2) y
C6 C7 1.377(2) ?
C6 C11 1.390(2) ?
C6 N1 1.406(2) y
C7 C8 1.388(2) ?
C7 H7 0.9300 ?
C8 C9 1.373(2) ?
C8 H8 0.9300 ?
C9 C10 1.3927(19) ?
C9 H9 0.9300 ?
C10 C11 1.3733(17) ?
C10 H10 0.9300 ?
C12 N1 1.451(2) y
C12 H12A 0.9600 ?
C12 H12B 0.9600 ?
C12 H12C 0.9600 ?
C13 O3 1.2060(10) y
C13 C14 1.4941(16) ?
C14 C19 1.3866(17) ?
C14 C15 1.3921(17) ?
C15 C16 1.3808(18) ?
C15 H15 0.9300 ?
C16 C17 1.381(2) ?
C16 H16 0.9300 ?
C17 C18 1.385(2) ?
C17 H17 0.9300 ?
C18 O4 1.363(2) y
C18 C19 1.3851(18) ?
C19 H19 0.9300 ?
C20 O4 1.425(2) y
C20 H20A 0.9600 ?
C20 H20B 0.9600 ?
C20 H20C 0.9600 ?
C21 O5 1.221(2) y
C21 C22 1.5132(17) ?
C22 C23 1.5360(17) ?
C22 H22A 0.9700 ?
C22 H22B 0.9700 ?
C23 C26 1.525(2) ?
C23 C25 1.5249(18) ?
C23 C24 1.5411(17) ?
C24 H24A 0.9700 ?
C24 H24B 0.9700 ?
C25 H25A 0.9600 ?
C25 H25B 0.9600 ?
C25 H25C 0.9600 ?
C26 H26A 0.9600 ?
C26 H26B 0.9600 ?
C26 H26C 0.9600 ?
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_site_symmetry_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
C12 H12A O2 . 0.96 2.52 2.896(2) 103.0
C2 H2 O2 2_776 0.98 2.46 3.434(2) 176.7
C10 H10 O3 2_665 0.93 2.43 3.201(2) 140.3
C15 H15 O2 2_776 0.93 2.44 3.320(2) 158.1
C20 H20C O3 2_765 0.96 2.58 3.483(3) 156.8
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
O1 C1 C2 C3 5.68(11)
C11 C1 C2 C3 -119.13(10)
C5 C1 C2 C3 122.90(10)
O1 C1 C2 C13 126.72(10)
C11 C1 C2 C13 1.90(14)
C5 C1 C2 C13 -116.07(10)
C13 C2 C3 C4 -124.66(11)
C1 C2 C3 C4 -4.75(12)
C13 C2 C3 C21 59.48(16)
C1 C2 C3 C21 179.40(12)
C21 C3 C4 O1 178.22(11)
C2 C3 C4 O1 2.03(15)
C21 C3 C4 C24 -0.9(2)
C2 C3 C4 C24 -177.05(11)
O1 C1 C5 O2 58.98(16)
C11 C1 C5 O2 176.24(13)
C2 C1 C5 O2 -56.98(16)
O1 C1 C5 N1 -121.95(10)
C11 C1 C5 N1 -4.68(12)
C2 C1 C5 N1 122.09(10)
C11 C6 C7 C8 0.0(2)
N1 C6 C7 C8 -179.14(13)
C6 C7 C8 C9 -0.3(2)
C7 C8 C9 C10 0.7(3)
C8 C9 C10 C11 -0.6(2)
C9 C10 C11 C6 0.25(19)
C9 C10 C11 C1 -178.76(13)
C7 C6 C11 C10 0.05(19)
N1 C6 C11 C10 179.32(11)
C7 C6 C11 C1 179.27(12)
N1 C6 C11 C1 -1.46(13)
O1 C1 C11 C10 -61.99(16)
C5 C1 C11 C10 -177.25(13)
C2 C1 C11 C10 60.39(17)
O1 C1 C11 C6 118.91(10)
C5 C1 C11 C6 3.64(12)
C2 C1 C11 C6 -118.72(11)
C3 C2 C13 O3 12.51(16)
C1 C2 C13 O3 -100.83(13)
C3 C2 C13 C14 -168.58(10)
C1 C2 C13 C14 78.09(12)
O3 C13 C14 C19 21.95(17)
C2 C13 C14 C19 -156.96(11)
O3 C13 C14 C15 -156.84(13)
C2 C13 C14 C15 24.25(17)
C19 C14 C15 C16 -1.5(2)
C13 C14 C15 C16 177.24(12)
C14 C15 C16 C17 1.9(2)
C15 C16 C17 C18 -0.7(2)
C16 C17 C18 O4 178.24(15)
C16 C17 C18 C19 -0.8(2)
O4 C18 C19 C14 -178.00(13)
C17 C18 C19 C14 1.1(2)
C15 C14 C19 C18 0.0(2)
C13 C14 C19 C18 -178.77(11)
C4 C3 C21 O5 -170.63(13)
C2 C3 C21 O5 4.8(2)
C4 C3 C21 C22 9.24(17)
C2 C3 C21 C22 -175.30(11)
O5 C21 C22 C23 141.83(13)
C3 C21 C22 C23 -38.04(15)
C21 C22 C23 C26 -64.41(14)
C21 C22 C23 C25 176.18(11)
C21 C22 C23 C24 56.86(14)
C3 C4 C24 C23 20.44(18)
O1 C4 C24 C23 -158.61(11)
C26 C23 C24 C4 75.03(14)
C25 C23 C24 C4 -164.81(11)
C22 C23 C24 C4 -45.77(14)
O2 C5 N1 C6 -176.83(13)
C1 C5 N1 C6 4.11(14)
O2 C5 N1 C12 3.3(2)
C1 C5 N1 C12 -175.79(12)
C7 C6 N1 C5 177.43(13)
C11 C6 N1 C5 -1.77(15)
C7 C6 N1 C12 -2.7(2)
C11 C6 N1 C12 178.13(12)
C3 C4 O1 C1 2.03(14)
C24 C4 O1 C1 -178.80(10)
C11 C1 O1 C4 124.02(10)
C5 C1 O1 C4 -124.13(10)
C2 C1 O1 C4 -4.94(11)
C17 C18 O4 C20 8.7(2)
C19 C18 O4 C20 -172.24(15)
