#------------------------------------------------------------------------------
#$Date: 2025-08-22 12:33:34 +0200 (Fri 22 de Aug de 2025) $
#$Revision: 301861 $
#$URL: svn://www.crystallography.net/cod/cif/7/15/17/7151724.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_7151724
loop_
_publ_author_name
'Böß, Esther'
'Hillringhaus, Tim'
'Nitsch, Jacqueline'
'Klussmann, Martin'
_publ_section_title
;
 Lewis acid-catalysed one pot synthesis of substituted xanthenes.
;
_journal_issue                   6
_journal_name_full               'Organic & biomolecular chemistry'
_journal_page_first              1744
_journal_page_last               1748
_journal_paper_doi               10.1039/C0OB00954G
_journal_volume                  9
_journal_year                    2011
_chemical_compound_source        'Et2O, pentane'
_chemical_formula_moiety         'C16 H16 O2'
_chemical_formula_sum            'C16 H16 O2'
_chemical_formula_weight         240.29
_space_group_IT_number           2
_symmetry_cell_setting           triclinic
_symmetry_Int_Tables_number      2
_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_block_code                BSR-BC-126-01
_audit_creation_date             2010-09-13
_audit_creation_method           SHELXL-97
_cell_angle_alpha                99.79(2)
_cell_angle_beta                 110.27(2)
_cell_angle_gamma                98.47(3)
_cell_formula_units_Z            2
_cell_length_a                   7.3745(19)
_cell_length_b                   8.763(3)
_cell_length_c                   10.395(2)
_cell_measurement_reflns_used    12671
_cell_measurement_temperature    100
_cell_measurement_theta_max      33.9961
_cell_measurement_theta_min      2.8224
_cell_volume                     605.3(3)
_computing_cell_refinement       'DENZO (Bruker AXS, 2006)'
_computing_data_collection       'DATCOL (Bruker AXS, 2006)'
_computing_data_reduction        'DENZO (Bruker AXS, 2006)'
_computing_molecular_graphics    'DIAMOND (Crystal Impact GbR, 2005)'
_computing_publication_material
;
OLEX2: a complete structure solution, refinement and analysis program.
Dolomanov et al., J. Appl. Cryst. (2009). 42, 339-341
;
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      100
_diffrn_detector_area_resol_mean 18.02
_diffrn_measured_fraction_theta_full 0.982
_diffrn_measured_fraction_theta_max 0.982
_diffrn_measurement_device_type  'Bruker AXS Enraf-Nonius KappaCCD'
_diffrn_measurement_method       'CCD φ- and ω-scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         '0.2 x 2mm^2^ focus rotating anode'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0273
_diffrn_reflns_av_sigmaI/netI    0.0354
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            11977
_diffrn_reflns_theta_full        34.06
_diffrn_reflns_theta_max         34.06
_diffrn_reflns_theta_min         2.83
_exptl_absorpt_coefficient_mu    0.086
_exptl_absorpt_correction_T_max  0.99359
_exptl_absorpt_correction_T_min  0.98013
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details   'SADABS (Bruker AXS, 2008)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.318
_exptl_crystal_description       prism
_exptl_crystal_F_000             256
_exptl_crystal_size_max          0.35
_exptl_crystal_size_mid          0.16
_exptl_crystal_size_min          0.08
_refine_diff_density_max         0.557
_refine_diff_density_min         -0.253
_refine_diff_density_rms         0.055
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.043
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     166
_refine_ls_number_reflns         4896
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.043
_refine_ls_R_factor_all          0.0618
_refine_ls_R_factor_gt           0.0456
_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)+(0.0699P)²+0.1150P] where P=(Fo²+2Fc²)/3
;
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1220
_refine_ls_wR_factor_ref         0.1339
_reflns_number_gt                3839
_reflns_number_total             4896
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            C0OB00954G.TXT
_cod_data_source_block           7104SADABS
_cod_depositor_comments
;
The following automatic conversions were performed:
'_symmetry_cell_setting' value 'TRICLINIC' changed to 'triclinic'
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 1555 2011-01-17 13:19:09Z saulius 
;
_cod_original_sg_symbol_Hall     '-p 1'
_cod_original_sg_symbol_H-M      P-1
_cod_database_code               7151724
loop_
_space_group_symop_id
_space_group_symop_operation_xyz
1 'x, y, z'
2 '-x, -y, -z'
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 0.74981(11) 0.22110(7) 0.59864(6) 0.01786(14) Uani 1 1 d . . .
O2 O 0.81735(10) 0.83486(7) 0.87933(7) 0.01916(14) Uani 1 1 d . . .
C1 C 0.73951(12) 0.18146(10) 0.46116(8) 0.01414(15) Uani 1 1 d . . .
C2 C 0.74027(13) 0.02305(10) 0.41310(9) 0.01631(16) Uani 1 1 d . . .
H2 H 0.7499 -0.0458 0.4729 0.020 Uiso 1 1 calc R . .
C3 C 0.72657(13) -0.03186(10) 0.27544(9) 0.01545(15) Uani 1 1 d . . .
C4 C 0.71019(13) 0.07476(10) 0.18802(8) 0.01537(15) Uani 1 1 d . . .
H4 H 0.6982 0.0387 0.0953 0.018 Uiso 1 1 calc R . .
C5 C 0.71145(12) 0.23390(10) 0.23636(8) 0.01402(15) Uani 1 1 d . . .
C6 C 0.72826(12) 0.29070(9) 0.37626(8) 0.01273(14) Uani 1 1 d . . .
C7 C 0.73530(12) 0.46301(9) 0.43274(8) 0.01341(15) Uani 1 1 d . . .
H7B H 0.8452 0.5293 0.4231 0.016 Uiso 1 1 calc R . .
H7A H 0.6140 0.4897 0.3768 0.016 Uiso 1 1 calc R . .
C8 C 0.75927(12) 0.49830(9) 0.58580(8) 0.01263(14) Uani 1 1 d . . .
C9 C 0.77678(12) 0.65393(10) 0.65826(8) 0.01392(15) Uani 1 1 d . . .
H9 H 0.7750 0.7357 0.6116 0.017 Uiso 1 1 calc R . .
C10 C 0.79689(12) 0.68746(10) 0.79948(8) 0.01444(15) Uani 1 1 d . . .
C11 C 0.79886(13) 0.56376(10) 0.86972(8) 0.01570(15) Uani 1 1 d . . .
H11 H 0.8112 0.5850 0.9635 0.019 Uiso 1 1 calc R . .
C12 C 0.78243(13) 0.41035(10) 0.79934(8) 0.01533(15) Uani 1 1 d . . .
H12 H 0.7844 0.3286 0.8459 0.018 Uiso 1 1 calc R . .
C13 C 0.76289(12) 0.37818(9) 0.65811(8) 0.01358(14) Uani 1 1 d . . .
C14 C 0.73303(15) -0.20214(11) 0.22357(10) 0.02034(18) Uani 1 1 d . . .
H14C H 0.8574 -0.2218 0.2797 0.031 Uiso 1 1 calc R . .
H14B H 0.7192 -0.2204 0.1266 0.031 Uiso 1 1 calc R . .
H14A H 0.6265 -0.2723 0.2315 0.031 Uiso 1 1 calc R . .
C15 C 0.69769(14) 0.34599(11) 0.14020(9) 0.01767(16) Uani 1 1 d . . .
H15C H 0.8167 0.4281 0.1781 0.027 Uiso 1 1 calc R . .
H15A H 0.5858 0.3927 0.1329 0.027 Uiso 1 1 calc R . .
H15B H 0.6818 0.2886 0.0483 0.027 Uiso 1 1 calc R . .
C16 C 0.80078(14) 0.96268(10) 0.80984(9) 0.01826(17) Uani 1 1 d . . .
H16C H 0.8204 1.0596 0.8770 0.027 Uiso 1 1 calc R . .
H16A H 0.6713 0.9408 0.7365 0.027 Uiso 1 1 calc R . .
H16B H 0.8995 0.9734 0.7694 0.027 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_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
0.00 0.00 1.00 0.0500
0.00 0.00 -1.00 0.0300
-1.00 0.00 0.00 0.1700
1.00 0.00 0.00 0.1800
0.00 -4.00 1.00 0.0600
0.00 1.00 0.00 0.0400
1.00 -3.00 0.00 0.1000
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
O1 C1 C2 114.58(7) . . ?
O1 C1 C6 123.05(7) . . ?
O1 C13 C8 123.68(7) . . ?
O1 C13 C12 115.16(7) . . ?
O2 C10 C9 125.22(8) . . ?
O2 C10 C11 115.26(7) . . ?
O2 C16 H16C 109.5 . . ?
O2 C16 H16A 109.5 . . ?
O2 C16 H16B 109.5 . . ?
C1 C2 H2 120.0 . . ?
C1 C6 C5 117.46(8) . . ?
C1 C6 C7 121.26(7) . . ?
C2 C1 C6 122.37(8) . . ?
C2 C3 C4 118.47(8) . . ?
C2 C3 C14 120.33(8) . . ?
C3 C2 C1 119.90(8) . . ?
C3 C2 H2 120.0 . . ?
C3 C4 H4 119.1 . . ?
C3 C14 H14C 109.5 . . ?
C3 C14 H14B 109.5 . . ?
C3 C14 H14A 109.5 . . ?
C4 C3 C14 121.19(8) . . ?
C4 C5 C6 120.03(8) . . ?
C4 C5 C15 120.26(7) . . ?
C5 C4 C3 121.73(8) . . ?
C5 C4 H4 119.1 . . ?
C5 C6 C7 121.28(7) . . ?
C5 C15 H15C 109.5 . . ?
C5 C15 H15A 109.5 . . ?
C5 C15 H15B 109.5 . . ?
C6 C5 C15 119.70(8) . . ?
C6 C7 H7B 109.1 . . ?
C6 C7 H7A 109.1 . . ?
H7B C7 H7A 107.9 . . ?
C8 C7 C6 112.28(7) . . ?
C8 C7 H7B 109.1 . . ?
C8 C7 H7A 109.1 . . ?
C8 C9 H9 119.6 . . ?
C8 C13 C12 121.17(8) . . ?
C9 C8 C7 120.46(7) . . ?
C9 C10 C11 119.52(8) . . ?
C10 O2 C16 117.41(7) . . ?
C10 C9 C8 120.88(7) . . ?
C10 C9 H9 119.6 . . ?
C10 C11 H11 120.0 . . ?
C11 C12 H12 120.0 . . ?
C11 C12 C13 120.03(8) . . ?
C12 C11 C10 119.97(8) . . ?
C12 C11 H11 120.0 . . ?
C13 O1 C1 118.47(7) . . ?
C13 C8 C7 121.11(7) . . ?
C13 C8 C9 118.43(7) . . ?
C13 C12 H12 120.0 . . ?
H14C C14 H14B 109.5 . . ?
H14C C14 H14A 109.5 . . ?
H14B C14 H14A 109.5 . . ?
H15C C15 H15A 109.5 . . ?
H15C C15 H15B 109.5 . . ?
H15A C15 H15B 109.5 . . ?
H16C C16 H16A 109.5 . . ?
H16C C16 H16B 109.5 . . ?
H16A C16 H16B 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 1.3846(10) . ?
O1 C13 1.3843(11) . ?
O2 C10 1.3679(11) . ?
O2 C16 1.4302(12) . ?
C1 C2 1.3946(12) . ?
C1 C6 1.4007(12) . ?
C2 H2 0.9300 . ?
C2 C3 1.3932(12) . ?
C3 C4 1.3997(12) . ?
C3 C14 1.5115(13) . ?
C4 H4 0.9300 . ?
C4 C5 1.3971(12) . ?
C5 C6 1.4102(11) . ?
C5 C15 1.5057(12) . ?
C6 C7 1.5106(12) . ?
C7 H7B 0.9700 . ?
C7 H7A 0.9700 . ?
C7 C8 1.5100(11) . ?
C8 C9 1.4054(12) . ?
C8 C13 1.3918(12) . ?
C9 H9 0.9300 . ?
C9 C10 1.3974(11) . ?
C10 C11 1.4054(12) . ?
C11 H11 0.9300 . ?
C11 C12 1.3832(12) . ?
C12 H12 0.9300 . ?
C12 C13 1.3987(11) . ?
C14 H14C 0.9600 . ?
C14 H14B 0.9600 . ?
C14 H14A 0.9600 . ?
C15 H15C 0.9600 . ?
C15 H15A 0.9600 . ?
C15 H15B 0.9600 . ?
C16 H16C 0.9600 . ?
C16 H16A 0.9600 . ?
C16 H16B 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
O1 C1 C2 C3 178.75(7) . . . . ?
O1 C1 C6 C5 -177.83(7) . . . . ?
O1 C1 C6 C7 2.58(13) . . . . ?
O2 C10 C11 C12 -178.96(8) . . . . ?
C1 O1 C13 C8 2.36(12) . . . . ?
C1 O1 C13 C12 -177.03(7) . . . . ?
C1 C2 C3 C4 -0.66(13) . . . . ?
C1 C2 C3 C14 178.28(8) . . . . ?
C1 C6 C7 C8 1.17(11) . . . . ?
C2 C1 C6 C5 1.87(13) . . . . ?
C2 C1 C6 C7 -177.72(8) . . . . ?
C2 C3 C4 C5 1.34(13) . . . . ?
C3 C4 C5 C6 -0.41(13) . . . . ?
C3 C4 C5 C15 178.76(8) . . . . ?
C4 C5 C6 C1 -1.17(12) . . . . ?
C4 C5 C6 C7 178.42(7) . . . . ?
C5 C6 C7 C8 -178.40(7) . . . . ?
C6 C1 C2 C3 -0.97(14) . . . . ?
C6 C7 C8 C9 177.44(7) . . . . ?
C6 C7 C8 C13 -3.11(11) . . . . ?
C7 C8 C9 C10 179.31(7) . . . . ?
C7 C8 C13 O1 1.51(13) . . . . ?
C7 C8 C13 C12 -179.14(7) . . . . ?
C8 C9 C10 O2 179.13(8) . . . . ?
C8 C9 C10 C11 -0.24(13) . . . . ?
C9 C8 C13 O1 -179.03(7) . . . . ?
C9 C8 C13 C12 0.32(13) . . . . ?
C9 C10 C11 C12 0.47(13) . . . . ?
C10 C11 C12 C13 -0.31(13) . . . . ?
C11 C12 C13 O1 179.31(7) . . . . ?
C11 C12 C13 C8 -0.09(13) . . . . ?
C13 O1 C1 C2 175.85(7) . . . . ?
C13 O1 C1 C6 -4.43(12) . . . . ?
C13 C8 C9 C10 -0.15(12) . . . . ?
C14 C3 C4 C5 -177.59(8) . . . . ?
C15 C5 C6 C1 179.66(7) . . . . ?
C15 C5 C6 C7 -0.75(12) . . . . ?
C16 O2 C10 C9 5.37(13) . . . . ?
C16 O2 C10 C11 -175.24(7) . . . . ?
loop_
_cod_changelog_entry_id
_cod_changelog_entry_author
_cod_changelog_entry_date
_cod_changelog_entry_text
1 'Vaitkus, Antanas' 2022-06-28T20:18:00+03:00
;
 Removed the '_chemical_name_systematic' and '_chemical_name_common'
 data items that had incorrect values.
;
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 PubChem 139190595
