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#$Date: 2025-08-22 00:26:11 +0300 (Fri, 22 Aug 2025) $
#$Revision: 301853 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/10/67/7106777.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_7106777
loop_
_publ_author_name
'Eliska Matousova'
'Ales Ruzicka'
'Jiri Kunes'
'Jarmila Kralova'
'Milan Pour'
_publ_section_title
;
 TFP as a ligand in Au(I)-catalyzed dihydropyran synthesis. Unprecedented
 rearrangement of dihydropyrans into cyclopentenones
;
_journal_name_full               Chem.Commun.
_journal_page_first              9390
_journal_paper_doi               10.1039/c1cc13525b
_journal_volume                  47
_journal_year                    2011
_chemical_formula_moiety         'C18 H18 O4'
_chemical_formula_sum            'C18 H18 O4'
_chemical_formula_weight         298.32
_space_group_IT_number           61
_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_Hall  '-P 2ac 2ab'
_symmetry_space_group_name_H-M   'P b c a'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   12.9230(7)
_cell_length_b                   7.4390(12)
_cell_length_c                   30.766(2)
_cell_measurement_reflns_used    16499
_cell_measurement_temperature    150(1)
_cell_measurement_theta_max      27.5
_cell_measurement_theta_min      1
_cell_volume                     2957.7(5)
_computing_cell_refinement       'COLLECT and DENZO'
_computing_data_collection
'COLLECT (Hooft, 1998) and DENZO (Otwinowski & Minor, 1997)'
_computing_data_reduction        'COLLECT and DENZO'
_computing_molecular_graphics    'PLATON (Spek, 2003)'
_computing_publication_material  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SIR92 (Altomare et al., 1994)'
_diffrn_ambient_temperature      150(1)
_diffrn_detector_area_resol_mean 9.091
_diffrn_measured_fraction_theta_full 0.993
_diffrn_measured_fraction_theta_max 0.993
_diffrn_measurement_device_type  'Bruker Nonius KappaCCD area detector'
_diffrn_measurement_method       'φ and ω scans to fill the Ewald sphere'
_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  0.0567
_diffrn_reflns_av_sigmaI/netI    0.0388
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       33
_diffrn_reflns_limit_l_min       -39
_diffrn_reflns_number            16377
_diffrn_reflns_theta_full        27.50
_diffrn_reflns_theta_max         27.50
_diffrn_reflns_theta_min         2.65
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.094
_exptl_absorpt_correction_T_max  0.986
_exptl_absorpt_correction_T_min  0.977
_exptl_absorpt_correction_type   integration
_exptl_absorpt_process_details
;
Gaussian integration (Coppens, 1970)
;
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.340
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             1264
_exptl_crystal_size_max          0.37
_exptl_crystal_size_mid          0.22
_exptl_crystal_size_min          0.16
_refine_diff_density_max         0.356
_refine_diff_density_min         -0.239
_refine_diff_density_rms         0.048
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.140
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     199
_refine_ls_number_reflns         3373
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.140
_refine_ls_R_factor_all          0.0853
_refine_ls_R_factor_gt           0.0548
_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)+(0.0353P)²+1.8542P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1065
_refine_ls_wR_factor_ref         0.1215
_reflns_number_gt                2474
_reflns_number_total             3373
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            c1cc13525b.txt
_cod_data_source_block           shelxl
_cod_original_cell_volume        2957.7(6)
_cod_database_code               7106777
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'x+1/2, -y+1/2, -z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, y, -z-1/2'
'-x-1/2, y-1/2, 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
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
O4 O -0.12654(11) 0.12408(18) 0.06346(4) 0.0307(3) Uani 1 1 d . . .
O1 O 0.05220(11) 0.07907(17) 0.07000(4) 0.0286(3) Uani 1 1 d . . .
O3 O 0.10478(11) 0.61251(18) 0.07203(5) 0.0351(4) Uani 1 1 d . . .
C6 C -0.04981(14) 0.5387(2) 0.14351(5) 0.0220(4) Uani 1 1 d . . .
O2 O 0.11328(11) 0.42544(19) 0.01546(4) 0.0326(3) Uani 1 1 d . . .
C16 C 0.07350(15) 0.4710(2) 0.04881(6) 0.0229(4) Uani 1 1 d . . .
C15 C -0.14985(15) 0.5937(2) 0.13736(6) 0.0264(4) Uani 1 1 d . . .
H15 H -0.1897 0.5375 0.1162 0.032 Uiso 1 1 d R . .
C1 C -0.01837(15) 0.3788(2) 0.07008(5) 0.0227(4) Uani 1 1 d . . .
H1 H -0.0810 0.4447 0.0618 0.027 Uiso 1 1 d R . .
C2 C -0.02800(15) 0.1876(2) 0.05282(6) 0.0249(4) Uani 1 1 d . . .
H2 H -0.0213 0.1905 0.0211 0.030 Uiso 1 1 d R . .
C7 C 0.01323(15) 0.6326(2) 0.17411(5) 0.0229(4) Uani 1 1 d . . .
C12 C -0.03210(17) 0.7740(3) 0.19897(6) 0.0288(4) Uani 1 1 d . . .
C5 C -0.01181(14) 0.3778(2) 0.11929(6) 0.0230(4) Uani 1 1 d . . .
C3 C 0.04517(18) 0.0584(3) 0.11616(6) 0.0340(5) Uani 1 1 d . . .
H3A H 0.1108 0.0143 0.1271 0.041 Uiso 1 1 d R . .
H3B H -0.0070 -0.0314 0.1227 0.041 Uiso 1 1 d R . .
C11 C 0.0286(2) 0.8679(3) 0.22956(7) 0.0404(6) Uani 1 1 d . . .
H11 H -0.0013 0.9589 0.2460 0.048 Uiso 1 1 d R . .
C8 C 0.12023(16) 0.5964(3) 0.18046(7) 0.0319(5) Uani 1 1 d . . .
H8 H 0.1521 0.5063 0.1643 0.038 Uiso 1 1 d R . .
C4 C 0.01826(15) 0.2288(3) 0.13927(6) 0.0284(4) Uani 1 1 d . . .
H4 H 0.0229 0.2303 0.1694 0.034 Uiso 1 1 d R . .
C18 C -0.14684(18) -0.0492(3) 0.04464(7) 0.0374(5) Uani 1 1 d . . .
H18A H -0.1377 -0.0435 0.0137 0.045 Uiso 1 1 d R . .
H18B H -0.2166 -0.0845 0.0511 0.045 Uiso 1 1 d R . .
H18C H -0.0997 -0.1357 0.0567 0.045 Uiso 1 1 d R . .
C17 C 0.19240(17) 0.7103(3) 0.05482(7) 0.0373(5) Uani 1 1 d . . .
H17A H 0.2522 0.6338 0.0544 0.045 Uiso 1 1 d R . .
H17B H 0.2059 0.8130 0.0729 0.045 Uiso 1 1 d R . .
H17C H 0.1771 0.7495 0.0258 0.045 Uiso 1 1 d R . .
C14 C -0.19401(16) 0.7324(3) 0.16210(6) 0.0321(5) Uani 1 1 d . . .
H14 H -0.2628 0.7643 0.1577 0.039 Uiso 1 1 d R . .
C9 C 0.17687(19) 0.6924(3) 0.21004(7) 0.0434(6) Uani 1 1 d . . .
H9 H 0.2470 0.6683 0.2136 0.052 Uiso 1 1 d R . .
C13 C -0.13729(17) 0.8199(3) 0.19223(7) 0.0344(5) Uani 1 1 d . . .
H13 H -0.1674 0.9107 0.2087 0.041 Uiso 1 1 d R . .
C10 C 0.1296(2) 0.8278(3) 0.23517(7) 0.0473(6) Uani 1 1 d . . .
H10 H 0.1682 0.8898 0.2558 0.057 Uiso 1 1 d 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 1 0 0.112
0 -1 0 0.178
0 0 -1 0.082
0 0 1 0.076
-1 0 0 0.073
1 0 0 0.120
1 1 0 0.110
-1 1 0 0.083
-1 -1 0 0.105
1 -1 0 0.143
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
C2 O4 C18 112.04(15) . . ?
C2 O1 C3 112.66(14) . . ?
C16 O3 C17 115.95(15) . . ?
C15 C6 C7 118.95(17) . . ?
C15 C6 C5 118.76(17) . . ?
C7 C6 C5 122.24(16) . . ?
O2 C16 O3 123.53(17) . . ?
O2 C16 C1 125.24(17) . . ?
O3 C16 C1 111.23(15) . . ?
C6 C15 C14 121.92(18) . . ?
C6 C15 H15 119.0 . . ?
C14 C15 H15 119.0 . . ?
C5 C1 C16 112.87(15) . . ?
C5 C1 C2 110.35(15) . . ?
C16 C1 C2 109.59(15) . . ?
C5 C1 H1 107.9 . . ?
C16 C1 H1 107.9 . . ?
C2 C1 H1 108.0 . . ?
O4 C2 O1 112.76(15) . . ?
O4 C2 C1 107.97(15) . . ?
O1 C2 C1 110.03(15) . . ?
O4 C2 H2 108.7 . . ?
O1 C2 H2 108.7 . . ?
C1 C2 H2 108.6 . . ?
C8 C7 C12 117.71(18) . . ?
C8 C7 C6 123.59(17) . . ?
C12 C7 C6 118.68(17) . . ?
C11 C12 C13 120.77(19) . . ?
C11 C12 C7 119.7(2) . . ?
C13 C12 C7 119.56(18) . . ?
C4 C5 C6 122.38(16) . . ?
C4 C5 C1 118.92(17) . . ?
C6 C5 C1 118.40(15) . . ?
O1 C3 C4 113.30(15) . . ?
O1 C3 H3A 109.0 . . ?
C4 C3 H3A 109.0 . . ?
O1 C3 H3B 108.8 . . ?
C4 C3 H3B 108.9 . . ?
H3A C3 H3B 107.7 . . ?
C10 C11 C12 120.9(2) . . ?
C10 C11 H11 119.6 . . ?
C12 C11 H11 119.5 . . ?
C9 C8 C7 120.8(2) . . ?
C9 C8 H8 119.6 . . ?
C7 C8 H8 119.6 . . ?
C5 C4 C3 123.83(17) . . ?
C5 C4 H4 118.1 . . ?
C3 C4 H4 118.0 . . ?
O4 C18 H18A 109.7 . . ?
O4 C18 H18B 109.5 . . ?
H18A C18 H18B 109.5 . . ?
O4 C18 H18C 109.3 . . ?
H18A C18 H18C 109.5 . . ?
H18B C18 H18C 109.5 . . ?
O3 C17 H17A 109.7 . . ?
O3 C17 H17B 109.3 . . ?
H17A C17 H17B 109.5 . . ?
O3 C17 H17C 109.4 . . ?
H17A C17 H17C 109.5 . . ?
H17B C17 H17C 109.5 . . ?
C13 C14 C15 120.42(19) . . ?
C13 C14 H14 119.8 . . ?
C15 C14 H14 119.8 . . ?
C8 C9 C10 120.4(2) . . ?
C8 C9 H9 119.9 . . ?
C10 C9 H9 119.7 . . ?
C14 C13 C12 120.36(19) . . ?
C14 C13 H13 119.9 . . ?
C12 C13 H13 119.8 . . ?
C11 C10 C9 120.5(2) . . ?
C11 C10 H10 119.7 . . ?
C9 C10 H10 119.9 . . ?
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
O4 C2 1.397(2) . ?
O4 C18 1.437(2) . ?
O1 C2 1.416(2) . ?
O1 C3 1.431(2) . ?
O3 C16 1.335(2) . ?
O3 C17 1.446(2) . ?
C6 C15 1.369(3) . ?
C6 C7 1.427(3) . ?
C6 C5 1.493(2) . ?
O2 C16 1.197(2) . ?
C16 C1 1.519(3) . ?
C15 C14 1.404(3) . ?
C15 H15 0.9301 . ?
C1 C5 1.517(2) . ?
C1 C2 1.524(2) . ?
C1 H1 0.9800 . ?
C2 H2 0.9799 . ?
C7 C8 1.422(3) . ?
C7 C12 1.427(3) . ?
C12 C11 1.410(3) . ?
C12 C13 1.417(3) . ?
C5 C4 1.326(3) . ?
C3 C4 1.495(3) . ?
C3 H3A 0.9699 . ?
C3 H3B 0.9700 . ?
C11 C10 1.351(3) . ?
C11 H11 0.9300 . ?
C8 C9 1.369(3) . ?
C8 H8 0.9300 . ?
C4 H4 0.9299 . ?
C18 H18A 0.9602 . ?
C18 H18B 0.9599 . ?
C18 H18C 0.9599 . ?
C17 H17A 0.9600 . ?
C17 H17B 0.9599 . ?
C17 H17C 0.9601 . ?
C14 C13 1.349(3) . ?
C14 H14 0.9300 . ?
C9 C10 1.409(4) . ?
C9 H9 0.9301 . ?
C13 H13 0.9299 . ?
C10 H10 0.9300 . ?
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 PubChem 101960488
