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#$Date: 2025-08-20 17:12:52 +0300 (Wed, 20 Aug 2025) $
#$Revision: 301832 $
#$URL: file:///home/coder/svn-repositories/cod/cif/4/10/65/4106530.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_4106530
loop_
_publ_author_name
'Yajing Lian'
'Huw M. L. Davies'
_publ_section_title
;
 Combined C-H Functionalization/Cope Rearrangement with Vinyl Ethers as a
 Surrogate for the Vinylogous Mukaiyama Aldol Reaction
;
_journal_name_full               'Journal of the American Chemical Society'
_journal_page_first              11940
_journal_page_last               11943
_journal_paper_doi               10.1021/ja2051155
_journal_volume                  133
_journal_year                    2011
_chemical_absolute_configuration ad
_chemical_formula_sum            'C25 H28 O3'
_chemical_formula_weight         376.47
_space_group_IT_number           4
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  'P 2yb'
_symmetry_space_group_name_H-M   'P 1 21 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                 103.0450(10)
_cell_angle_gamma                90.00
_cell_formula_units_Z            2
_cell_length_a                   8.46960(10)
_cell_length_b                   8.2702(2)
_cell_length_c                   15.7541(3)
_cell_measurement_reflns_used    2283
_cell_measurement_temperature    173(2)
_cell_measurement_theta_max      69.18
_cell_measurement_theta_min      5.48
_cell_volume                     1075.02(4)
_computing_cell_refinement       'Bruker SAINT'
_computing_data_collection       'Bruker APEX2'
_computing_data_reduction        'Bruker SAINT'
_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      173(2)
_diffrn_measured_fraction_theta_full 0.937
_diffrn_measured_fraction_theta_max 0.937
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0143
_diffrn_reflns_av_sigmaI/netI    0.0203
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            5719
_diffrn_reflns_theta_full        69.41
_diffrn_reflns_theta_max         69.41
_diffrn_reflns_theta_min         2.88
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.591
_exptl_absorpt_correction_T_max  0.9598
_exptl_absorpt_correction_T_min  0.8472
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   sadabs
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.163
_exptl_crystal_description       rod
_exptl_crystal_F_000             404
_exptl_crystal_size_max          0.29
_exptl_crystal_size_mid          0.08
_exptl_crystal_size_min          0.07
_refine_diff_density_max         0.107
_refine_diff_density_min         -0.148
_refine_diff_density_rms         0.028
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.0(2)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.017
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     253
_refine_ls_number_reflns         2970
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.017
_refine_ls_R_factor_all          0.0343
_refine_ls_R_factor_gt           0.0320
_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)+(0.0520P)²+0.1070P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0834
_refine_ls_wR_factor_ref         0.0855
_reflns_number_gt                2805
_reflns_number_total             2970
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ja2051155_si_003.cif
_cod_data_source_block           yl_9_128cope
_cod_database_code               4106530
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y+1/2, -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
C1 C 1.4043(2) 0.6046(3) 0.85998(13) 0.0478(5) Uani 1 1 d .
H1A H 1.4473 0.5356 0.8226 0.057 Uiso 1 1 calc R
C2 C 1.4896(3) 0.7417(3) 0.89399(15) 0.0578(6) Uani 1 1 d .
H2A H 1.5896 0.7663 0.8792 0.069 Uiso 1 1 calc R
C3 C 1.4308(3) 0.8420(3) 0.94880(14) 0.0604(6) Uani 1 1 d .
H3A H 1.4906 0.9349 0.9728 0.072 Uiso 1 1 calc R
C4 C 1.2841(3) 0.8073(3) 0.96885(15) 0.0596(6) Uani 1 1 d .
H4A H 1.2416 0.8773 1.0060 0.072 Uiso 1 1 calc R
C5 C 1.1989(2) 0.6702(3) 0.93476(14) 0.0537(5) Uani 1 1 d .
H5A H 1.0985 0.6467 0.9494 0.064 Uiso 1 1 calc R
C6 C 1.2575(2) 0.5664(2) 0.87958(11) 0.0399(4) Uani 1 1 d .
C7 C 1.1624(2) 0.4209(2) 0.83824(12) 0.0418(4) Uani 1 1 d .
H7A H 1.2378 0.3525 0.8131 0.050 Uiso 1 1 calc R
C8 C 1.0254(2) 0.4754(2) 0.76233(14) 0.0458(5) Uani 1 1 d .
H8A H 0.9687 0.5685 0.7815 0.055 Uiso 1 1 calc R
H8B H 1.0731 0.5126 0.7139 0.055 Uiso 1 1 calc R
C9 C 0.9043(2) 0.3446(2) 0.72949(13) 0.0412(4) Uani 1 1 d .
H9A H 0.8273 0.3636 0.6764 0.049 Uiso 1 1 calc R
C10 C 0.8969(2) 0.2055(2) 0.76886(12) 0.0367(4) Uani 1 1 d .
C11 C 1.0118(2) 0.1647(3) 0.85419(13) 0.0464(5) Uani 1 1 d .
H11A H 1.0954 0.0888 0.8432 0.056 Uiso 1 1 calc R
H11B H 0.9511 0.1098 0.8927 0.056 Uiso 1 1 calc R
C12 C 1.0945(3) 0.3146(3) 0.90003(13) 0.0509(5) Uani 1 1 d .
H12A H 1.0153 0.3774 0.9242 0.061 Uiso 1 1 calc R
H12B H 1.1836 0.2812 0.9491 0.061 Uiso 1 1 calc R
C13 C 0.7720(2) 0.0802(2) 0.72938(12) 0.0372(4) Uani 1 1 d .
H13A H 0.6988 0.1273 0.6764 0.045 Uiso 1 1 calc R
C14 C 0.8457(2) -0.0781(2) 0.70347(12) 0.0380(4) Uani 1 1 d .
H14A H 0.8935 -0.1394 0.7579 0.046 Uiso 1 1 calc R
C15 C 0.71372(19) -0.1802(2) 0.64851(13) 0.0391(4) Uani 1 1 d .
H15A H 0.6720 -0.1464 0.5901 0.047 Uiso 1 1 calc R
C16 C 0.6514(2) -0.3119(2) 0.67447(13) 0.0400(4) Uani 1 1 d .
H16A H 0.6915 -0.3487 0.7325 0.048 Uiso 1 1 calc R
C17 C 0.52157(19) -0.4044(2) 0.61666(12) 0.0378(4) Uani 1 1 d .
C18 C 0.3380(3) -0.6205(3) 0.61112(15) 0.0641(7) Uani 1 1 d .
H18A H 0.3053 -0.7006 0.6497 0.096 Uiso 1 1 calc R
H18B H 0.3780 -0.6762 0.5652 0.096 Uiso 1 1 calc R
H18C H 0.2447 -0.5532 0.5847 0.096 Uiso 1 1 calc R
C19 C 0.9789(2) -0.0482(2) 0.65480(13) 0.0398(4) Uani 1 1 d .
C20 C 1.1336(2) -0.1105(3) 0.68780(17) 0.0527(5) Uani 1 1 d .
H20A H 1.1558 -0.1672 0.7416 0.063 Uiso 1 1 calc R
C21 C 1.2542(3) -0.0907(3) 0.6431(2) 0.0684(7) Uani 1 1 d .
H21A H 1.3595 -0.1325 0.6666 0.082 Uiso 1 1 calc R
C22 C 1.2228(3) -0.0102(4) 0.5643(2) 0.0775(9) Uani 1 1 d .
H22A H 1.3051 0.0000 0.5324 0.093 Uiso 1 1 calc R
C23 C 1.0710(3) 0.0554(3) 0.53193(16) 0.0672(7) Uani 1 1 d .
H23A H 1.0501 0.1136 0.4785 0.081 Uiso 1 1 calc R
C24 C 0.9491(2) 0.0368(3) 0.57695(14) 0.0499(5) Uani 1 1 d .
H24A H 0.8451 0.0824 0.5544 0.060 Uiso 1 1 calc R
C25 C 0.5708(2) 0.1526(3) 0.80587(16) 0.0567(6) Uani 1 1 d .
H25A H 0.5089 0.1115 0.8469 0.085 Uiso 1 1 calc R
H25B H 0.4960 0.1843 0.7514 0.085 Uiso 1 1 calc R
H25C H 0.6346 0.2466 0.8313 0.085 Uiso 1 1 calc R
O1 O 0.46510(16) -0.51970(17) 0.66093(9) 0.0496(4) Uani 1 1 d .
O2 O 0.47060(15) -0.38154(17) 0.53901(9) 0.0474(3) Uani 1 1 d .
O3 O 0.67607(14) 0.03017(16) 0.78851(9) 0.0455(3) 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
C6 C1 C2 121.1(2)
C6 C1 H1A 119.4
C2 C1 H1A 119.4
C3 C2 C1 120.5(2)
C3 C2 H2A 119.8
C1 C2 H2A 119.8
C2 C3 C4 119.5(2)
C2 C3 H3A 120.2
C4 C3 H3A 120.2
C3 C4 C5 119.9(2)
C3 C4 H4A 120.0
C5 C4 H4A 120.0
C4 C5 C6 121.27(19)
C4 C5 H5A 119.4
C6 C5 H5A 119.4
C1 C6 C5 117.68(19)
C1 C6 C7 120.23(17)
C5 C6 C7 122.03(17)
C6 C7 C12 115.27(16)
C6 C7 C8 109.70(16)
C12 C7 C8 109.95(15)
C6 C7 H7A 107.2
C12 C7 H7A 107.2
C8 C7 H7A 107.2
C9 C8 C7 113.23(16)
C9 C8 H8A 108.9
C7 C8 H8A 108.9
C9 C8 H8B 108.9
C7 C8 H8B 108.9
H8A C8 H8B 107.7
C10 C9 C8 124.73(17)
C10 C9 H9A 117.6
C8 C9 H9A 117.6
C9 C10 C11 121.74(18)
C9 C10 C13 120.60(17)
C11 C10 C13 117.66(16)
C10 C11 C12 112.04(17)
C10 C11 H11A 109.2
C12 C11 H11A 109.2
C10 C11 H11B 109.2
C12 C11 H11B 109.2
H11A C11 H11B 107.9
C7 C12 C11 111.55(17)
C7 C12 H12A 109.3
C11 C12 H12A 109.3
C7 C12 H12B 109.3
C11 C12 H12B 109.3
H12A C12 H12B 108.0
O3 C13 C10 112.26(15)
O3 C13 C14 104.49(14)
C10 C13 C14 113.74(13)
O3 C13 H13A 108.7
C10 C13 H13A 108.7
C14 C13 H13A 108.7
C15 C14 C19 109.85(15)
C15 C14 C13 109.56(13)
C19 C14 C13 112.68(15)
C15 C14 H14A 108.2
C19 C14 H14A 108.2
C13 C14 H14A 108.2
C16 C15 C14 125.62(18)
C16 C15 H15A 117.2
C14 C15 H15A 117.2
C15 C16 C17 122.24(18)
C15 C16 H16A 118.9
C17 C16 H16A 118.9
O2 C17 O1 123.36(17)
O2 C17 C16 125.91(17)
O1 C17 C16 110.73(15)
O1 C18 H18A 109.5
O1 C18 H18B 109.5
H18A C18 H18B 109.5
O1 C18 H18C 109.5
H18A C18 H18C 109.5
H18B C18 H18C 109.5
C24 C19 C20 119.01(19)
C24 C19 C14 121.42(16)
C20 C19 C14 119.55(19)
C21 C20 C19 120.6(2)
C21 C20 H20A 119.7
C19 C20 H20A 119.7
C20 C21 C22 120.2(2)
C20 C21 H21A 119.9
C22 C21 H21A 119.9
C21 C22 C23 119.7(2)
C21 C22 H22A 120.2
C23 C22 H22A 120.2
C22 C23 C24 120.4(3)
C22 C23 H23A 119.8
C24 C23 H23A 119.8
C19 C24 C23 120.1(2)
C19 C24 H24A 120.0
C23 C24 H24A 120.0
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
C17 O1 C18 116.10(15)
C25 O3 C13 113.24(15)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
C1 C6 1.384(3)
C1 C2 1.386(3)
C1 H1A 0.9500
C2 C3 1.370(3)
C2 H2A 0.9500
C3 C4 1.380(3)
C3 H3A 0.9500
C4 C5 1.386(3)
C4 H4A 0.9500
C5 C6 1.390(3)
C5 H5A 0.9500
C6 C7 1.512(3)
C7 C12 1.518(3)
C7 C8 1.534(3)
C7 H7A 1.0000
C8 C9 1.501(3)
C8 H8A 0.9900
C8 H8B 0.9900
C9 C10 1.315(3)
C9 H9A 0.9500
C10 C11 1.509(3)
C10 C13 1.511(2)
C11 C12 1.523(3)
C11 H11A 0.9900
C11 H11B 0.9900
C12 H12A 0.9900
C12 H12B 0.9900
C13 O3 1.429(2)
C13 C14 1.544(2)
C13 H13A 1.0000
C14 C15 1.508(2)
C14 C19 1.520(2)
C14 H14A 1.0000
C15 C16 1.316(3)
C15 H15A 0.9500
C16 C17 1.474(2)
C16 H16A 0.9500
C17 O2 1.217(2)
C17 O1 1.332(2)
C18 O1 1.445(2)
C18 H18A 0.9800
C18 H18B 0.9800
C18 H18C 0.9800
C19 C24 1.386(3)
C19 C20 1.395(3)
C20 C21 1.375(3)
C20 H20A 0.9500
C21 C22 1.382(4)
C21 H21A 0.9500
C22 C23 1.382(4)
C22 H22A 0.9500
C23 C24 1.387(3)
C23 H23A 0.9500
C24 H24A 0.9500
C25 O3 1.416(2)
C25 H25A 0.9800
C25 H25B 0.9800
C25 H25C 0.9800
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
C6 C1 C2 C3 0.7(3)
C1 C2 C3 C4 -1.2(3)
C2 C3 C4 C5 1.1(4)
C3 C4 C5 C6 -0.6(4)
C2 C1 C6 C5 -0.2(3)
C2 C1 C6 C7 176.94(18)
C4 C5 C6 C1 0.1(3)
C4 C5 C6 C7 -176.93(19)
C1 C6 C7 C12 134.73(19)
C5 C6 C7 C12 -48.3(3)
C1 C6 C7 C8 -100.5(2)
C5 C6 C7 C8 76.5(2)
C6 C7 C8 C9 -167.97(17)
C12 C7 C8 C9 -40.2(2)
C7 C8 C9 C10 10.8(3)
C8 C9 C10 C11 1.0(3)
C8 C9 C10 C13 -178.81(18)
C9 C10 C11 C12 17.6(3)
C13 C10 C11 C12 -162.56(17)
C6 C7 C12 C11 -175.70(16)
C8 C7 C12 C11 59.7(2)
C10 C11 C12 C7 -48.0(2)
C9 C10 C13 O3 -125.49(19)
C11 C10 C13 O3 54.7(2)
C9 C10 C13 C14 116.1(2)
C11 C10 C13 C14 -63.7(2)
O3 C13 C14 C15 68.91(18)
C10 C13 C14 C15 -168.34(15)
O3 C13 C14 C19 -168.48(14)
C10 C13 C14 C19 -45.7(2)
C19 C14 C15 C16 129.77(19)
C13 C14 C15 C16 -106.0(2)
C14 C15 C16 C17 179.59(16)
C15 C16 C17 O2 8.1(3)
C15 C16 C17 O1 -172.00(17)
C15 C14 C19 C24 63.0(2)
C13 C14 C19 C24 -59.4(2)
C15 C14 C19 C20 -115.46(19)
C13 C14 C19 C20 122.10(18)
C24 C19 C20 C21 -1.2(3)
C14 C19 C20 C21 177.33(19)
C19 C20 C21 C22 -0.8(3)
C20 C21 C22 C23 2.3(4)
C21 C22 C23 C24 -1.8(4)
C20 C19 C24 C23 1.6(3)
C14 C19 C24 C23 -176.9(2)
C22 C23 C24 C19 -0.1(3)
O2 C17 O1 C18 0.6(3)
C16 C17 O1 C18 -179.30(17)
C10 C13 O3 C25 68.91(19)
C14 C13 O3 C25 -167.38(15)
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 PubChem 139116493
