#------------------------------------------------------------------------------
#$Date: 2025-08-22 12:33:34 +0200 (Fri 22 de Aug de 2025) $
#$Revision: 301861 $
#$URL: svn://www.crystallography.net/cod/cif/7/15/06/7150650.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_7150650
loop_
_publ_author_name
'Bruder, Marjorie'
'Smith, Stephen J.'
'Blake, Alexander J.'
'Moody, Christopher J.'
_publ_section_title
;
 Synthesis of (+-)-likonide B (smenochromene D) using a regioselective
 Claisen rearrangement, separation of the enantiomers and
 stereochemical assignment
;
_journal_issue                   10
_journal_name_full               'Organic & Biomolecular Chemistry'
_journal_page_first              2127
_journal_page_last               2134
_journal_paper_doi               10.1039/b901358j
_journal_volume                  7
_journal_year                    2009
_chemical_formula_moiety         'C22 H28 O3'
_chemical_formula_sum            'C22 H28 O3'
_chemical_formula_weight         340.44
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 1 21/c 1'
_atom_sites_solution_hydrogens
'sp2-bound methyl H atoms from delta-F; others placed geometrically'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           'enCIFer editing of SHELXL97 CIF output'
_cell_angle_alpha                90.00
_cell_angle_beta                 103.091(2)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   12.3277(8)
_cell_length_b                   9.6466(7)
_cell_length_c                   15.9180(11)
_cell_measurement_reflns_used    5150
_cell_measurement_temperature    150(2)
_cell_measurement_theta_max      27.4
_cell_measurement_theta_min      2.5
_cell_volume                     1843.8(2)
_computing_cell_refinement       'Bruker SAINT version 6.36A (Bruker, 2000)'
_computing_data_collection       'Bruker SMART version 5.625 (Bruker, 2001)'
_computing_data_reduction        'Bruker SAINT; Bruker SHELXTL (Bruker, 2001)'
_computing_publication_material
'enCIFer (Allen et al., 2004); PLATON (Spek, 2003)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      150(2)
_diffrn_measured_fraction_theta_full 0.995
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measurement_device_type  'Bruker SMART APEX CCD area detector'
_diffrn_measurement_method       omega
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.069
_diffrn_reflns_av_sigmaI/netI    0.040
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            16435
_diffrn_reflns_theta_full        27.50
_diffrn_reflns_theta_max         27.50
_diffrn_reflns_theta_min         2.49
_diffrn_standards_decay_%        0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.080
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.226
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             736
_exptl_crystal_size_max          0.79
_exptl_crystal_size_mid          0.76
_exptl_crystal_size_min          0.50
_refine_diff_density_max         0.33
_refine_diff_density_min         -0.21
_refine_diff_density_rms         0.05
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.06
_refine_ls_hydrogen_treatment    'rigid rotor; riding model'
_refine_ls_matrix_type           full
_refine_ls_number_parameters     228
_refine_ls_number_reflns         4213
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.06
_refine_ls_R_factor_all          0.0481
_refine_ls_R_factor_gt           0.0436
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.069P)²+0.329P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.120
_refine_ls_wR_factor_ref         0.124
_reflns_number_gt                3689
_reflns_number_total             4213
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            b901358j.txt
_cod_data_source_block           bzfude
_cod_original_cell_volume        1843.8(4)
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               7150650
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -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
C1 C 0.88460(9) 1.04112(12) 0.20663(7) 0.0243(2) Uani 1 1 d . . .
H1 H 0.9636 1.0373 0.2182 0.029 Uiso 1 1 calc R . .
C2 C 0.83318(9) 1.16254(12) 0.20375(7) 0.0255(2) Uani 1 1 d . . .
H2 H 0.8766 1.2448 0.2121 0.031 Uiso 1 1 calc R . .
C3 C 0.70805(9) 1.17425(11) 0.18766(7) 0.0231(2) Uani 1 1 d . . .
O3 O 0.65774(6) 1.04413(8) 0.20667(5) 0.02423(19) Uani 1 1 d . . .
C4 C 0.65506(10) 1.21866(11) 0.09442(7) 0.0255(2) Uani 1 1 d . . .
H4A H 0.5796 1.2548 0.0933 0.031 Uiso 1 1 calc R . .
H4B H 0.6993 1.2966 0.0794 0.031 Uiso 1 1 calc R . .
C5 C 0.64448(9) 1.10870(12) 0.02343(7) 0.0257(2) Uani 1 1 d . . .
H5A H 0.6141 1.0234 0.0439 0.031 Uiso 1 1 calc R . .
H5B H 0.5888 1.1419 -0.0275 0.031 Uiso 1 1 calc R . .
C6 C 0.74878(9) 1.06974(12) -0.00596(7) 0.0249(2) Uani 1 1 d . . .
H6 H 0.8158 1.1172 0.0192 0.030 Uiso 1 1 calc R . .
C7 C 0.75247(9) 0.97298(12) -0.06485(7) 0.0259(2) Uani 1 1 d . . .
C8 C 0.85637(10) 0.94483(12) -0.09745(7) 0.0275(3) Uani 1 1 d . . .
H8A H 0.9198 0.9922 -0.0588 0.033 Uiso 1 1 calc R . .
H8B H 0.8468 0.9869 -0.1554 0.033 Uiso 1 1 calc R . .
C9 C 0.88673(10) 0.79136(13) -0.10360(7) 0.0277(3) Uani 1 1 d . . .
H9A H 0.8229 0.7431 -0.1411 0.033 Uiso 1 1 calc R . .
H9B H 0.9505 0.7848 -0.1317 0.033 Uiso 1 1 calc R . .
C10 C 0.91661(9) 0.71746(12) -0.01831(7) 0.0246(2) Uani 1 1 d . . .
H10 H 0.9721 0.7604 0.0251 0.030 Uiso 1 1 calc R . .
C11 C 0.87497(9) 0.59941(12) 0.00386(7) 0.0251(2) Uani 1 1 d . . .
C12 C 0.91975(9) 0.53897(12) 0.09188(7) 0.0259(2) Uani 1 1 d . . .
H12A H 0.9439 0.4424 0.0857 0.031 Uiso 1 1 calc R . .
H12B H 0.9858 0.5928 0.1214 0.031 Uiso 1 1 calc R . .
O12 O 0.83777(7) 0.53996(8) 0.14471(5) 0.0265(2) Uani 1 1 d . . .
C13 C 0.67733(11) 1.27811(12) 0.25068(8) 0.0304(3) Uani 1 1 d . . .
H13A H 0.7114 1.2497 0.3099 0.046 Uiso 1 1 calc R . .
H13B H 0.5962 1.2811 0.2428 0.046 Uiso 1 1 calc R . .
H13C H 0.7047 1.3703 0.2398 0.046 Uiso 1 1 calc R . .
C14 C 0.65096(11) 0.89102(17) -0.10680(10) 0.0447(4) Uani 1 1 d . . .
H14A H 0.6503 0.8031 -0.0761 0.067 Uiso 1 1 calc R . .
H14B H 0.6524 0.8723 -0.1670 0.067 Uiso 1 1 calc R . .
H14C H 0.5839 0.9442 -0.1046 0.067 Uiso 1 1 calc R . .
C15 C 0.78317(12) 0.51650(16) -0.05193(9) 0.0404(3) Uani 1 1 d . . .
H15A H 0.7573 0.5637 -0.1074 0.061 Uiso 1 1 calc R . .
H15B H 0.7212 0.5075 -0.0231 0.061 Uiso 1 1 calc R . .
H15C H 0.8111 0.4242 -0.0617 0.061 Uiso 1 1 calc R . .
C16 C 0.86372(9) 0.78562(12) 0.17732(7) 0.0227(2) Uani 1 1 d . . .
H16 H 0.9413 0.7782 0.1799 0.027 Uiso 1 1 calc R . .
C17 C 0.79789(9) 0.66928(11) 0.15909(7) 0.0224(2) Uani 1 1 d . . .
O18 O 0.62344(7) 0.56102(8) 0.13425(6) 0.0307(2) Uani 1 1 d . . .
C18 C 0.68304(9) 0.67970(11) 0.15576(7) 0.0229(2) Uani 1 1 d . . .
C19 C 0.63818(9) 0.80597(11) 0.17305(7) 0.0231(2) Uani 1 1 d . . .
H19 H 0.5614 0.8127 0.1733 0.028 Uiso 1 1 calc R . .
C20 C 0.70599(9) 0.92211(11) 0.18988(7) 0.0212(2) Uani 1 1 d . . .
C21 C 0.81962(9) 0.91408(11) 0.19203(7) 0.0213(2) Uani 1 1 d . . .
C22 C 0.50734(10) 0.56509(14) 0.13074(12) 0.0418(3) Uani 1 1 d . . .
H22A H 0.4748 0.4736 0.1142 0.063 Uiso 1 1 calc R . .
H22B H 0.4719 0.6340 0.0880 0.063 Uiso 1 1 calc R . .
H22C H 0.4952 0.5905 0.1875 0.063 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
C2 C1 C21 119.78(10) . . ?
C2 C1 H1 120.1 . . ?
C21 C1 H1 120.1 . . ?
C1 C2 C3 122.24(10) . . ?
C1 C2 H2 118.9 . . ?
C3 C2 H2 118.9 . . ?
O3 C3 C2 111.45(9) . . ?
O3 C3 C13 104.35(8) . . ?
C2 C3 C13 109.51(9) . . ?
O3 C3 C4 109.33(9) . . ?
C2 C3 C4 112.22(9) . . ?
C13 C3 C4 109.68(9) . . ?
C20 O3 C3 118.25(8) . . ?
C5 C4 C3 117.66(9) . . ?
C5 C4 H4A 107.9 . . ?
C3 C4 H4A 107.9 . . ?
C5 C4 H4B 107.9 . . ?
C3 C4 H4B 107.9 . . ?
H4A C4 H4B 107.2 . . ?
C6 C5 C4 117.61(10) . . ?
C6 C5 H5A 107.9 . . ?
C4 C5 H5A 107.9 . . ?
C6 C5 H5B 107.9 . . ?
C4 C5 H5B 107.9 . . ?
H5A C5 H5B 107.2 . . ?
C7 C6 C5 124.02(11) . . ?
C7 C6 H6 118.0 . . ?
C5 C6 H6 118.0 . . ?
C6 C7 C14 121.60(11) . . ?
C6 C7 C8 122.32(11) . . ?
C14 C7 C8 115.98(10) . . ?
C7 C8 C9 115.65(9) . . ?
C7 C8 H8A 108.4 . . ?
C9 C8 H8A 108.4 . . ?
C7 C8 H8B 108.4 . . ?
C9 C8 H8B 108.4 . . ?
H8A C8 H8B 107.4 . . ?
C10 C9 C8 114.39(9) . . ?
C10 C9 H9A 108.7 . . ?
C8 C9 H9A 108.7 . . ?
C10 C9 H9B 108.7 . . ?
C8 C9 H9B 108.7 . . ?
H9A C9 H9B 107.6 . . ?
C11 C10 C9 128.00(11) . . ?
C11 C10 H10 116.0 . . ?
C9 C10 H10 116.0 . . ?
C10 C11 C15 125.73(11) . . ?
C10 C11 C12 119.84(10) . . ?
C15 C11 C12 114.43(10) . . ?
O12 C12 C11 112.34(9) . . ?
O12 C12 H12A 109.1 . . ?
C11 C12 H12A 109.1 . . ?
O12 C12 H12B 109.1 . . ?
C11 C12 H12B 109.1 . . ?
H12A C12 H12B 107.9 . . ?
C17 O12 C12 115.00(8) . . ?
C3 C13 H13A 109.5 . . ?
C3 C13 H13B 109.5 . . ?
H13A C13 H13B 109.5 . . ?
C3 C13 H13C 109.5 . . ?
H13A C13 H13C 109.5 . . ?
H13B C13 H13C 109.5 . . ?
C7 C14 H14A 109.5 . . ?
C7 C14 H14B 109.5 . . ?
H14A C14 H14B 109.5 . . ?
C7 C14 H14C 109.5 . . ?
H14A C14 H14C 109.5 . . ?
H14B C14 H14C 109.5 . . ?
C11 C15 H15A 109.5 . . ?
C11 C15 H15B 109.5 . . ?
H15A C15 H15B 109.5 . . ?
C11 C15 H15C 109.5 . . ?
H15A C15 H15C 109.5 . . ?
H15B C15 H15C 109.5 . . ?
C17 C16 C21 121.75(10) . . ?
C17 C16 H16 119.1 . . ?
C21 C16 H16 119.1 . . ?
C16 C17 O12 123.86(9) . . ?
C16 C17 C18 119.30(10) . . ?
O12 C17 C18 116.84(10) . . ?
C18 O18 C22 117.92(9) . . ?
O18 C18 C19 124.76(10) . . ?
O18 C18 C17 115.47(9) . . ?
C19 C18 C17 119.76(10) . . ?
C20 C19 C18 119.76(10) . . ?
C20 C19 H19 120.1 . . ?
C18 C19 H19 120.1 . . ?
O3 C20 C19 117.49(9) . . ?
O3 C20 C21 121.32(10) . . ?
C19 C20 C21 121.17(10) . . ?
C16 C21 C20 118.20(10) . . ?
C16 C21 C1 123.67(10) . . ?
C20 C21 C1 118.10(10) . . ?
O18 C22 H22A 109.5 . . ?
O18 C22 H22B 109.5 . . ?
H22A C22 H22B 109.5 . . ?
O18 C22 H22C 109.5 . . ?
H22A C22 H22C 109.5 . . ?
H22B C22 H22C 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
C1 C2 1.3276(16) . ?
C1 C21 1.4537(15) . ?
C1 H1 0.9500 . ?
C2 C3 1.5096(15) . ?
C2 H2 0.9500 . ?
C3 O3 1.4618(13) . ?
C3 C13 1.5249(15) . ?
C3 C4 1.5408(15) . ?
O3 C20 1.3722(13) . ?
C4 C5 1.5338(15) . ?
C4 H4A 0.9900 . ?
C4 H4B 0.9900 . ?
C5 C6 1.5118(15) . ?
C5 H5A 0.9900 . ?
C5 H5B 0.9900 . ?
C6 C7 1.3310(16) . ?
C6 H6 0.9500 . ?
C7 C14 1.5029(17) . ?
C7 C8 1.5115(15) . ?
C8 C9 1.5357(17) . ?
C8 H8A 0.9900 . ?
C8 H8B 0.9900 . ?
C9 C10 1.5035(16) . ?
C9 H9A 0.9900 . ?
C9 H9B 0.9900 . ?
C10 C11 1.3293(16) . ?
C10 H10 0.9500 . ?
C11 C15 1.5012(17) . ?
C11 C12 1.5025(16) . ?
C12 O12 1.4538(12) . ?
C12 H12A 0.9900 . ?
C12 H12B 0.9900 . ?
O12 C17 1.3789(13) . ?
C13 H13A 0.9800 . ?
C13 H13B 0.9800 . ?
C13 H13C 0.9800 . ?
C14 H14A 0.9800 . ?
C14 H14B 0.9800 . ?
C14 H14C 0.9800 . ?
C15 H15A 0.9800 . ?
C15 H15B 0.9800 . ?
C15 H15C 0.9800 . ?
C16 C17 1.3768(16) . ?
C16 C21 1.3943(15) . ?
C16 H16 0.9500 . ?
C17 C18 1.4084(15) . ?
O18 C18 1.3615(14) . ?
O18 C22 1.4201(15) . ?
C18 C19 1.3908(15) . ?
C19 C20 1.3872(15) . ?
C19 H19 0.9500 . ?
C20 C21 1.3955(15) . ?
C22 H22A 0.9800 . ?
C22 H22B 0.9800 . ?
C22 H22C 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
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C21 C1 C2 C3 1.42(16) . . . . ?
C1 C2 C3 O3 20.34(14) . . . . ?
C1 C2 C3 C13 135.28(11) . . . . ?
C1 C2 C3 C4 -102.66(12) . . . . ?
C2 C3 O3 C20 -34.50(12) . . . . ?
C13 C3 O3 C20 -152.59(9) . . . . ?
C4 C3 O3 C20 90.14(11) . . . . ?
O3 C3 C4 C5 -47.53(13) . . . . ?
C2 C3 C4 C5 76.66(12) . . . . ?
C13 C3 C4 C5 -161.38(10) . . . . ?
C3 C4 C5 C6 -75.92(13) . . . . ?
C4 C5 C6 C7 177.74(11) . . . . ?
C5 C6 C7 C14 -1.06(19) . . . . ?
C5 C6 C7 C8 175.16(10) . . . . ?
C6 C7 C8 C9 134.86(12) . . . . ?
C14 C7 C8 C9 -48.72(15) . . . . ?
C7 C8 C9 C10 -64.74(13) . . . . ?
C8 C9 C10 C11 127.85(12) . . . . ?
C9 C10 C11 C15 -3.08(19) . . . . ?
C9 C10 C11 C12 177.38(10) . . . . ?
C10 C11 C12 O12 113.48(11) . . . . ?
C15 C11 C12 O12 -66.11(13) . . . . ?
C11 C12 O12 C17 -59.42(12) . . . . ?
C21 C16 C17 O12 -179.50(9) . . . . ?
C21 C16 C17 C18 -0.46(16) . . . . ?
C12 O12 C17 C16 -41.69(14) . . . . ?
C12 O12 C17 C18 139.24(10) . . . . ?
C22 O18 C18 C19 -1.29(17) . . . . ?
C22 O18 C18 C17 179.39(11) . . . . ?
C16 C17 C18 O18 177.70(10) . . . . ?
O12 C17 C18 O18 -3.19(14) . . . . ?
C16 C17 C18 C19 -1.66(15) . . . . ?
O12 C17 C18 C19 177.46(9) . . . . ?
O18 C18 C19 C20 -176.58(10) . . . . ?
C17 C18 C19 C20 2.71(16) . . . . ?
C3 O3 C20 C19 -153.68(9) . . . . ?
C3 O3 C20 C21 28.09(14) . . . . ?
C18 C19 C20 O3 -179.91(9) . . . . ?
C18 C19 C20 C21 -1.68(16) . . . . ?
C17 C16 C21 C20 1.48(15) . . . . ?
C17 C16 C21 C1 -176.37(10) . . . . ?
O3 C20 C21 C16 177.76(9) . . . . ?
C19 C20 C21 C16 -0.40(15) . . . . ?
O3 C20 C21 C1 -4.27(15) . . . . ?
C19 C20 C21 C1 177.57(10) . . . . ?
C2 C1 C21 C16 167.17(10) . . . . ?
C2 C1 C21 C20 -10.68(15) . . . . ?
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 PubChem 15699648
