#------------------------------------------------------------------------------
#$Date: 2016-03-21 03:15:31 +0200 (Mon, 21 Mar 2016) $
#$Revision: 178427 $
#$URL: svn://www.crystallography.net/cod/cif/4/02/48/4024806.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/
#
# All data on this site have been placed in the public domain by the
# contributors.
#
data_4024806
loop_
_publ_author_name
'Hongfeng Li'
'Jingyu Yang'
'Yuanhong Liu'
'Yanzhong Li'
_publ_section_title
;
Iron-Catalyzed Cascade Arene-Aldehyde Addition/Cyclizations for the
Highly Efficient Synthesis of Xanthenes and Its Analogous: Observation of a
C-C Bond Cleavage in Indole-Based Triarylmethanes
;
_journal_name_full               'Journal of Organic Chemistry'
_journal_page_first              6797
_journal_page_last               6801
_journal_paper_doi               10.1021/jo9012354
_journal_volume                  74
_journal_year                    2009
_chemical_formula_sum            'C25 H20 O3'
_chemical_formula_weight         368.41
_chemical_name_systematic
; 
 ? 
;
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2yn'
_symmetry_space_group_name_H-M   'P 1 21/n 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 98.181(4)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   11.6750(19)
_cell_length_b                   7.9242(13)
_cell_length_c                   20.616(4)
_cell_measurement_reflns_used    2028
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      42.722
_cell_measurement_theta_min      5.515
_cell_volume                     1887.8(5)
_computing_cell_refinement       'Bruker SMART'
_computing_data_collection       'Bruker SMART'
_computing_data_reduction        'Bruker SHELXTL'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_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  0.0477
_diffrn_reflns_av_sigmaI/netI    0.0534
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       25
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            10020
_diffrn_reflns_theta_full        25.99
_diffrn_reflns_theta_max         25.99
_diffrn_reflns_theta_min         1.90
_exptl_absorpt_coefficient_mu    0.084
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.76205
_exptl_absorpt_correction_type   empirical
_exptl_absorpt_process_details   sadabs
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.296
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prismatic
_exptl_crystal_F_000             776
_exptl_crystal_size_max          0.307
_exptl_crystal_size_mid          0.265
_exptl_crystal_size_min          0.073
_refine_diff_density_max         0.244
_refine_diff_density_min         -0.129
_refine_diff_density_rms         0.032
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.916
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     255
_refine_ls_number_reflns         3717
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.916
_refine_ls_R_factor_all          0.0827
_refine_ls_R_factor_gt           0.0473
_refine_ls_shift/su_max          0.022
_refine_ls_shift/su_mean         0.003
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0533P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1060
_refine_ls_wR_factor_ref         0.1177
_reflns_number_gt                2180
_reflns_number_total             3717
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jo9012354_si_003.cif
_cod_data_source_block           cd29173
_cod_depositor_comments
;
The following automatic conversions were performed:
'_symmetry_cell_setting' value 'Monoclinic' changed to 'monoclinic'
according to '/home/saulius/struct/CIF-dictionaries/cif_core.dic'
dictionary named 'cif_core.dic' version 2.4.1 from 2010-06-29.

Automatic conversion script
Id: cif_fix_enum 1527 2010-12-29 10:47:43Z saulius 
;
_cod_original_sg_symbol_H-M      P2(1)/n
_cod_database_code               4024806
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -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
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
O1 O 0.58776(12) 0.20574(18) 1.05114(6) 0.0726(4) Uani 1 1 d . . .
O2 O 0.33182(12) 0.3167(2) 0.80976(7) 0.0862(5) Uani 1 1 d . . .
O3 O 0.94921(11) 0.26251(19) 0.73985(6) 0.0743(4) Uani 1 1 d . . .
C1 C 0.69316(16) 0.1248(2) 1.05694(10) 0.0573(5) Uani 1 1 d . . .
C2 C 0.75040(19) 0.1126(3) 1.12038(11) 0.0766(6) Uani 1 1 d . . .
H2 H 0.7174 0.1569 1.1552 0.092 Uiso 1 1 calc R . .
C3 C 0.8558(2) 0.0350(3) 1.13133(12) 0.0826(7) Uani 1 1 d . . .
H3 H 0.8948 0.0270 1.1738 0.099 Uiso 1 1 calc R . .
C4 C 0.90419(17) -0.0309(3) 1.08041(12) 0.0748(7) Uani 1 1 d . . .
H4 H 0.9754 -0.0854 1.0881 0.090 Uiso 1 1 calc R . .
C5 C 0.84682(16) -0.0163(2) 1.01755(11) 0.0634(5) Uani 1 1 d . . .
H5 H 0.8810 -0.0596 0.9830 0.076 Uiso 1 1 calc R . .
C6 C 0.73908(15) 0.0614(2) 1.00427(9) 0.0492(5) Uani 1 1 d . . .
C7 C 0.67504(14) 0.0702(2) 0.93522(9) 0.0503(5) Uani 1 1 d . . .
H7 H 0.6506 -0.0455 0.9236 0.060 Uiso 1 1 calc R . .
C8 C 0.56441(14) 0.1724(2) 0.93267(9) 0.0483(5) Uani 1 1 d . . .
C9 C 0.52675(15) 0.2305(2) 0.98922(9) 0.0524(5) Uani 1 1 d . . .
C10 C 0.42437(16) 0.3185(2) 0.98699(10) 0.0617(5) Uani 1 1 d . . .
H10 H 0.4010 0.3571 1.0256 0.074 Uiso 1 1 calc R . .
C11 C 0.35673(15) 0.3496(2) 0.92809(10) 0.0613(5) Uani 1 1 d . . .
H11 H 0.2877 0.4089 0.9267 0.074 Uiso 1 1 calc R . .
C12 C 0.39178(16) 0.2926(2) 0.87139(10) 0.0597(5) Uani 1 1 d . . .
C13 C 0.49512(15) 0.2048(2) 0.87369(9) 0.0574(5) Uani 1 1 d . . .
H13 H 0.5183 0.1669 0.8349 0.069 Uiso 1 1 calc R . .
C14 C 0.74942(14) 0.1253(2) 0.88418(9) 0.0482(5) Uani 1 1 d . . .
C16 C 0.83085(16) 0.0566(3) 0.78502(10) 0.0651(6) Uani 1 1 d . . .
H16 H 0.8390 -0.0211 0.7522 0.078 Uiso 1 1 calc R . .
C15 C 0.76502(16) 0.0168(2) 0.83411(10) 0.0620(5) Uani 1 1 d . . .
H15 H 0.7298 -0.0887 0.8330 0.074 Uiso 1 1 calc R . .
C17 C 0.88329(15) 0.2105(3) 0.78542(9) 0.0554(5) Uani 1 1 d . . .
C18 C 0.87324(14) 0.3285(2) 0.83603(9) 0.0507(5) Uani 1 1 d . . .
C19 C 0.80452(14) 0.2844(2) 0.88600(8) 0.0450(4) Uani 1 1 d . . .
C20 C 0.79836(16) 0.4032(2) 0.93618(10) 0.0585(5) Uani 1 1 d . . .
H20 H 0.7543 0.3786 0.9692 0.070 Uiso 1 1 calc R . .
C21 C 0.85549(19) 0.5536(3) 0.93747(12) 0.0798(7) Uani 1 1 d . . .
H21 H 0.8508 0.6288 0.9716 0.096 Uiso 1 1 calc R . .
C22 C 0.92038(19) 0.5958(3) 0.88862(13) 0.0849(7) Uani 1 1 d . . .
H22 H 0.9587 0.6989 0.8901 0.102 Uiso 1 1 calc R . .
C23 C 0.92809(16) 0.4862(3) 0.83829(11) 0.0676(6) Uani 1 1 d . . .
H23 H 0.9703 0.5165 0.8051 0.081 Uiso 1 1 calc R . .
C24 C 0.22381(19) 0.4021(4) 0.80552(12) 0.1046(9) Uani 1 1 d . . .
H24A H 0.1725 0.3392 0.8289 0.157 Uiso 1 1 calc R . .
H24B H 0.1904 0.4122 0.7604 0.157 Uiso 1 1 calc R . .
H24C H 0.2357 0.5125 0.8245 0.157 Uiso 1 1 calc R . .
C25 C 0.9618(2) 0.1502(3) 0.68767(11) 0.1005(9) Uani 1 1 d . . .
H25A H 1.0009 0.0498 0.7050 0.151 Uiso 1 1 calc R . .
H25B H 1.0063 0.2038 0.6577 0.151 Uiso 1 1 calc R . .
H25C H 0.8868 0.1211 0.6650 0.151 Uiso 1 1 calc R . .
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'
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 O1 C9 118.82(14) . . ?
C12 O2 C24 116.97(17) . . ?
C17 O3 C25 117.60(18) . . ?
C6 C1 O1 123.12(17) . . ?
C6 C1 C2 122.09(18) . . ?
O1 C1 C2 114.79(18) . . ?
C3 C2 C1 119.3(2) . . ?
C3 C2 H2 120.3 . . ?
C1 C2 H2 120.3 . . ?
C2 C3 C4 120.5(2) . . ?
C2 C3 H3 119.7 . . ?
C4 C3 H3 119.7 . . ?
C3 C4 C5 119.5(2) . . ?
C3 C4 H4 120.3 . . ?
C5 C4 H4 120.3 . . ?
C4 C5 C6 121.8(2) . . ?
C4 C5 H5 119.1 . . ?
C6 C5 H5 119.1 . . ?
C1 C6 C5 116.74(18) . . ?
C1 C6 C7 122.08(16) . . ?
C5 C6 C7 121.16(17) . . ?
C6 C7 C8 111.18(14) . . ?
C6 C7 C14 114.21(14) . . ?
C8 C7 C14 112.91(14) . . ?
C6 C7 H7 105.9 . . ?
C8 C7 H7 105.9 . . ?
C14 C7 H7 105.9 . . ?
C9 C8 C13 117.56(17) . . ?
C9 C8 C7 121.29(16) . . ?
C13 C8 C7 121.10(16) . . ?
C10 C9 O1 115.62(16) . . ?
C10 C9 C8 121.25(17) . . ?
O1 C9 C8 123.14(16) . . ?
C11 C10 C9 120.45(18) . . ?
C11 C10 H10 119.8 . . ?
C9 C10 H10 119.8 . . ?
C12 C11 C10 119.45(18) . . ?
C12 C11 H11 120.3 . . ?
C10 C11 H11 120.3 . . ?
O2 C12 C11 124.67(18) . . ?
O2 C12 C13 115.30(18) . . ?
C11 C12 C13 120.03(18) . . ?
C8 C13 C12 121.26(17) . . ?
C8 C13 H13 119.4 . . ?
C12 C13 H13 119.4 . . ?
C15 C14 C19 118.00(17) . . ?
C15 C14 C7 119.29(16) . . ?
C19 C14 C7 122.71(16) . . ?
C17 C16 C15 119.51(19) . . ?
C17 C16 H16 120.2 . . ?
C15 C16 H16 120.2 . . ?
C14 C15 C16 123.33(18) . . ?
C14 C15 H15 118.3 . . ?
C16 C15 H15 118.3 . . ?
O3 C17 C16 124.34(19) . . ?
O3 C17 C18 115.00(18) . . ?
C16 C17 C18 120.65(17) . . ?
C23 C18 C17 121.79(18) . . ?
C23 C18 C19 119.51(18) . . ?
C17 C18 C19 118.70(17) . . ?
C20 C19 C14 123.05(16) . . ?
C20 C19 C18 117.13(16) . . ?
C14 C19 C18 119.79(16) . . ?
C21 C20 C19 121.51(18) . . ?
C21 C20 H20 119.2 . . ?
C19 C20 H20 119.2 . . ?
C20 C21 C22 120.9(2) . . ?
C20 C21 H21 119.5 . . ?
C22 C21 H21 119.5 . . ?
C23 C22 C21 120.0(2) . . ?
C23 C22 H22 120.0 . . ?
C21 C22 H22 120.0 . . ?
C22 C23 C18 120.86(19) . . ?
C22 C23 H23 119.6 . . ?
C18 C23 H23 119.6 . . ?
O2 C24 H24A 109.5 . . ?
O2 C24 H24B 109.5 . . ?
H24A C24 H24B 109.5 . . ?
O2 C24 H24C 109.5 . . ?
H24A C24 H24C 109.5 . . ?
H24B C24 H24C 109.5 . . ?
O3 C25 H25A 109.5 . . ?
O3 C25 H25B 109.5 . . ?
H25A C25 H25B 109.5 . . ?
O3 C25 H25C 109.5 . . ?
H25A C25 H25C 109.5 . . ?
H25B C25 H25C 109.5 . . ?
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 1.378(2) . ?
O1 C9 1.384(2) . ?
O2 C12 1.374(2) . ?
O2 C24 1.423(2) . ?
O3 C17 1.360(2) . ?
O3 C25 1.420(2) . ?
C1 C6 1.373(2) . ?
C1 C2 1.385(3) . ?
C2 C3 1.365(3) . ?
C2 H2 0.9300 . ?
C3 C4 1.365(3) . ?
C3 H3 0.9300 . ?
C4 C5 1.376(3) . ?
C4 H4 0.9300 . ?
C5 C6 1.392(2) . ?
C5 H5 0.9300 . ?
C6 C7 1.512(2) . ?
C7 C8 1.519(2) . ?
C7 C14 1.521(2) . ?
C7 H7 0.9800 . ?
C8 C9 1.382(2) . ?
C8 C13 1.385(2) . ?
C9 C10 1.379(2) . ?
C10 C11 1.373(2) . ?
C10 H10 0.9300 . ?
C11 C12 1.369(3) . ?
C11 H11 0.9300 . ?
C12 C13 1.388(2) . ?
C13 H13 0.9300 . ?
C14 C15 1.376(2) . ?
C14 C19 1.413(2) . ?
C16 C17 1.364(3) . ?
C16 C15 1.391(3) . ?
C16 H16 0.9300 . ?
C15 H15 0.9300 . ?
C17 C18 1.418(3) . ?
C18 C23 1.401(2) . ?
C18 C19 1.436(2) . ?
C19 C20 1.408(2) . ?
C20 C21 1.364(2) . ?
C20 H20 0.9300 . ?
C21 C22 1.384(3) . ?
C21 H21 0.9300 . ?
C22 C23 1.366(3) . ?
C22 H22 0.9300 . ?
C23 H23 0.9300 . ?
C24 H24A 0.9600 . ?
C24 H24B 0.9600 . ?
C24 H24C 0.9600 . ?
C25 H25A 0.9600 . ?
C25 H25B 0.9600 . ?
C25 H25C 0.9600 . ?
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
C9 O1 C1 C6 -2.6(3) . . . . ?
C9 O1 C1 C2 177.12(17) . . . . ?
C6 C1 C2 C3 -0.1(3) . . . . ?
O1 C1 C2 C3 -179.80(19) . . . . ?
C1 C2 C3 C4 -0.4(3) . . . . ?
C2 C3 C4 C5 1.1(3) . . . . ?
C3 C4 C5 C6 -1.3(3) . . . . ?
O1 C1 C6 C5 179.59(16) . . . . ?
C2 C1 C6 C5 -0.1(3) . . . . ?
O1 C1 C6 C7 -2.1(3) . . . . ?
C2 C1 C6 C7 178.20(18) . . . . ?
C4 C5 C6 C1 0.8(3) . . . . ?
C4 C5 C6 C7 -177.53(17) . . . . ?
C1 C6 C7 C8 6.2(2) . . . . ?
C5 C6 C7 C8 -175.63(15) . . . . ?
C1 C6 C7 C14 135.39(17) . . . . ?
C5 C6 C7 C14 -46.4(2) . . . . ?
C6 C7 C8 C9 -6.2(2) . . . . ?
C14 C7 C8 C9 -136.12(17) . . . . ?
C6 C7 C8 C13 176.48(15) . . . . ?
C14 C7 C8 C13 46.6(2) . . . . ?
C1 O1 C9 C10 -177.40(16) . . . . ?
C1 O1 C9 C8 2.5(3) . . . . ?
C13 C8 C9 C10 -0.5(3) . . . . ?
C7 C8 C9 C10 -177.84(16) . . . . ?
C13 C8 C9 O1 179.70(16) . . . . ?
C7 C8 C9 O1 2.3(3) . . . . ?
O1 C9 C10 C11 -179.71(17) . . . . ?
C8 C9 C10 C11 0.4(3) . . . . ?
C9 C10 C11 C12 -0.1(3) . . . . ?
C24 O2 C12 C11 -2.3(3) . . . . ?
C24 O2 C12 C13 178.27(19) . . . . ?
C10 C11 C12 O2 -179.65(17) . . . . ?
C10 C11 C12 C13 -0.2(3) . . . . ?
C9 C8 C13 C12 0.1(3) . . . . ?
C7 C8 C13 C12 177.54(16) . . . . ?
O2 C12 C13 C8 179.67(16) . . . . ?
C11 C12 C13 C8 0.2(3) . . . . ?
C6 C7 C14 C15 118.22(18) . . . . ?
C8 C7 C14 C15 -113.45(18) . . . . ?
C6 C7 C14 C19 -61.4(2) . . . . ?
C8 C7 C14 C19 67.0(2) . . . . ?
C19 C14 C15 C16 -0.8(3) . . . . ?
C7 C14 C15 C16 179.55(18) . . . . ?
C17 C16 C15 C14 -0.1(3) . . . . ?
C25 O3 C17 C16 1.5(3) . . . . ?
C25 O3 C17 C18 -179.56(17) . . . . ?
C15 C16 C17 O3 -179.86(16) . . . . ?
C15 C16 C17 C18 1.3(3) . . . . ?
O3 C17 C18 C23 -0.2(2) . . . . ?
C16 C17 C18 C23 178.73(17) . . . . ?
O3 C17 C18 C19 179.59(14) . . . . ?
C16 C17 C18 C19 -1.4(3) . . . . ?
C15 C14 C19 C20 -177.57(16) . . . . ?
C7 C14 C19 C20 2.0(3) . . . . ?
C15 C14 C19 C18 0.6(2) . . . . ?
C7 C14 C19 C18 -179.77(15) . . . . ?
C23 C18 C19 C20 -1.4(2) . . . . ?
C17 C18 C19 C20 178.77(16) . . . . ?
C23 C18 C19 C14 -179.71(15) . . . . ?
C17 C18 C19 C14 0.5(2) . . . . ?
C14 C19 C20 C21 178.00(18) . . . . ?
C18 C19 C20 C21 -0.2(3) . . . . ?
C19 C20 C21 C22 1.0(3) . . . . ?
C20 C21 C22 C23 -0.1(4) . . . . ?
C21 C22 C23 C18 -1.5(3) . . . . ?
C17 C18 C23 C22 -177.86(19) . . . . ?
C19 C18 C23 C22 2.3(3) . . . . ?
