#------------------------------------------------------------------------------
#$Date: 2017-10-13 03:48:21 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201957 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/01/56/2015619.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/. The original data for this entry
# were provided by IUCr Journals, http://journals.iucr.org/.
#
# The file may be used within the scientific community so long as
# proper attribution is given to the journal article from which the
# data were obtained.
#
data_2015619
loop_
_publ_author_name
'Langer, Vratislav'
'Li, Shiming'
'Lundquist, Knut'
_publ_section_title
;
 Chalcone epoxide intermediates in the syntheses of lignin-related
 phenylcoumarans
;
_journal_coeditor_code           SK3047
_journal_issue                   10
_journal_name_full               'Acta Crystallographica Section C'
_journal_page_first              o625
_journal_page_last               o627
_journal_paper_doi               10.1107/S0108270106036900
_journal_volume                  62
_journal_year                    2006
_chemical_formula_iupac          'C23 H26 O7'
_chemical_formula_moiety         'C23 H26 O7'
_chemical_formula_sum            'C23 H26 O7'
_chemical_formula_weight         414.44
_chemical_name_systematic
;
(2R*,3S*)-1-(3,4-dimethoxyphenyl)-3-{3-methoxy-2-[(2R*)-tetrahydropyran-
2-yloxy]phenyl}-2,3-epoxy-1-propanone
;
_space_group_IT_number           9
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  'C -2yc'
_symmetry_space_group_name_H-M   'C 1 c 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                 125.2850(10)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   14.4281(5)
_cell_length_b                   18.8386(7)
_cell_length_c                   9.0887(3)
_cell_measurement_reflns_used    7078
_cell_measurement_temperature    173(2)
_cell_measurement_theta_max      32.09
_cell_measurement_theta_min      2.49
_cell_volume                     2016.52(12)
_computing_cell_refinement       'SAINT (Bruker, 2003)'
_computing_data_collection       'SMART (Bruker, 2003)'
_computing_data_reduction        'SAINT and SADABS (Sheldrick, 2003)'
_computing_molecular_graphics    'DIAMOND (Brandenburg, 2005)'
_computing_publication_material  SHELXTL
_computing_structure_refinement  SHELXTL
_computing_structure_solution    'SHELXTL (Bruker, 2003)'
_diffrn_ambient_temperature      173(2)
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.945
_diffrn_measurement_device_type  'Siemens SMART CCD area-detector'
_diffrn_measurement_method       'ω 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  0.0335
_diffrn_reflns_av_sigmaI/netI    0.0239
_diffrn_reflns_limit_h_max       21
_diffrn_reflns_limit_h_min       -21
_diffrn_reflns_limit_k_max       28
_diffrn_reflns_limit_k_min       -28
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            18037
_diffrn_reflns_theta_full        31.00
_diffrn_reflns_theta_max         33.15
_diffrn_reflns_theta_min         2.04
_diffrn_standards_decay_%        0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.101
_exptl_absorpt_correction_T_max  0.9821
_exptl_absorpt_correction_T_min  0.6081
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SADABS; Sheldrick, 2003)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.365
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             880
_exptl_crystal_size_max          0.42
_exptl_crystal_size_mid          0.22
_exptl_crystal_size_min          0.18
_refine_diff_density_max         0.324
_refine_diff_density_min         -0.181
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.007
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     274
_refine_ls_number_reflns         3639
_refine_ls_number_restraints     2
_refine_ls_restrained_S_all      1.007
_refine_ls_R_factor_all          0.0445
_refine_ls_R_factor_gt           0.0363
_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)+(0.0720P)²+0.0200P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0937
_refine_ls_wR_factor_ref         0.0994
_reflns_number_gt                3193
_reflns_number_total             3639
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            sk3047.cif
_cod_data_source_block           I
_cod_original_sg_symbol_H-M      'C c'
_cod_database_code               2015619
_cod_database_fobs_code          2015619
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'x, -y, z+1/2'
'x+1/2, y+1/2, z'
'x+1/2, -y+1/2, z+1/2'
loop_
_atom_site_type_symbol
_atom_site_label
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_occupancy
O O1 0.05273(12) 0.98417(7) 0.28979(18) 0.0336(3) Uani d . 1
O O2 0.18225(12) 0.91853(7) 0.59272(16) 0.0340(3) Uani d . 1
O O3 0.35467(12) 0.71243(6) 0.46411(18) 0.0336(3) Uani d . 1
O O4 0.39322(12) 0.67530(6) 0.21211(19) 0.0327(3) Uani d . 1
O O5 0.72969(10) 0.88301(7) 0.24914(16) 0.0293(2) Uani d . 1
O O6 0.62968(10) 0.83612(6) 0.42010(14) 0.0239(2) Uani d . 1
O O7 0.56041(10) 0.95177(6) 0.31418(15) 0.0276(2) Uani d . 1
C C1 0.24632(12) 0.81536(8) 0.3156(2) 0.0227(3) Uani d . 1
C C2 0.18137(13) 0.85382(8) 0.1563(2) 0.0252(3) Uani d . 1
H H2 0.1821 0.8411 0.0558 0.030 Uiso calc R 1
C C3 0.11515(14) 0.91087(9) 0.1425(2) 0.0277(3) Uani d . 1
H H3 0.0700 0.9363 0.0324 0.033 Uiso calc R 1
C C4 0.11537(13) 0.93045(8) 0.2897(2) 0.0257(3) Uani d . 1
C C5 0.18502(13) 0.89333(8) 0.4551(2) 0.0250(3) Uani d . 1
C C6 0.24838(13) 0.83617(8) 0.4662(2) 0.0241(3) Uani d . 1
H H6 0.2937 0.8107 0.5761 0.029 Uiso calc R 1
C C7 -0.02777(16) 1.01764(10) 0.1194(3) 0.0355(4) Uani d . 1
H H7A 0.0126 1.0397 0.0738 0.053 Uiso calc R 1
H H7B -0.0698 1.0541 0.1351 0.053 Uiso calc R 1
H H7C -0.0809 0.9820 0.0330 0.053 Uiso calc R 1
C C8 0.24673(18) 0.88047(11) 0.7592(2) 0.0375(4) Uani d . 1
H H8A 0.2203 0.8312 0.7392 0.056 Uiso calc R 1
H H8B 0.2369 0.9028 0.8467 0.056 Uiso calc R 1
H H8C 0.3272 0.8814 0.8058 0.056 Uiso calc R 1
C C9 0.31515(14) 0.75263(8) 0.3367(2) 0.0246(3) Uani d . 1
C C10 0.34295(13) 0.74188(8) 0.2022(2) 0.0247(3) Uani d . 1
H H10 0.2917 0.7643 0.0808 0.030 Uiso calc R 1
C C11 0.46590(13) 0.73650(8) 0.2785(2) 0.0243(3) Uani d . 1
H H11 0.5192 0.7405 0.4126 0.029 Uiso calc R 1
C C12 0.51144(13) 0.76015(8) 0.1763(2) 0.0235(3) Uani d . 1
C C13 0.47217(14) 0.73067(9) 0.0081(2) 0.0285(3) Uani d . 1
H H13 0.4147 0.6953 -0.0436 0.034 Uiso calc R 1
C C14 0.51799(15) 0.75361(10) -0.0817(2) 0.0308(3) Uani d . 1
H H14 0.4911 0.7343 -0.1965 0.037 Uiso calc R 1
C C15 0.60361(14) 0.80494(9) -0.0048(2) 0.0291(3) Uani d . 1
H H15 0.6348 0.8199 -0.0674 0.035 Uiso calc R 1
C C16 0.64375(13) 0.83445(8) 0.1628(2) 0.0249(3) Uani d . 1
C C17 0.59533(12) 0.81245(8) 0.25264(19) 0.0223(3) Uani d . 1
C C18 0.77905(17) 0.90537(10) 0.1583(3) 0.0332(3) Uani d . 1
H H18A 0.8079 0.8639 0.1315 0.050 Uiso calc R 1
H H18B 0.8417 0.9382 0.2356 0.050 Uiso calc R 1
H H18C 0.7214 0.9293 0.0456 0.050 Uiso calc R 1
C C19 0.64536(13) 0.91141(8) 0.4610(2) 0.0242(3) Uani d . 1
H H19 0.7209 0.9260 0.4901 0.029 Uiso calc R 1
C C20 0.64751(13) 0.91913(8) 0.62880(19) 0.0254(3) Uani d . 1
H H20A 0.7009 0.8840 0.7198 0.030 Uiso calc R 1
H H20B 0.6754 0.9671 0.6803 0.030 Uiso calc R 1
C C21 0.53056(15) 0.90814(8) 0.5887(2) 0.0265(3) Uani d . 1
H H21A 0.5328 0.9190 0.6974 0.032 Uiso calc R 1
H H21B 0.5068 0.8581 0.5548 0.032 Uiso calc R 1
C C22 0.44625(14) 0.95694(9) 0.4349(2) 0.0272(3) Uani d . 1
H H22A 0.3689 0.9484 0.4028 0.033 Uiso calc R 1
H H22B 0.4664 1.0071 0.4728 0.033 Uiso calc R 1
C C23 0.44844(14) 0.94287(9) 0.2723(2) 0.0269(3) Uani d . 1
H H23A 0.4220 0.8938 0.2291 0.032 Uiso calc R 1
H H23B 0.3954 0.9758 0.1740 0.032 Uiso calc R 1
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 0.0000 '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 0.0000 '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
C1 C9 C10 118.37(13)
O3 C9 C1 122.03(14)
O3 C9 C10 119.47(14)
O4 C10 C9 115.59(13)
O4 C10 C11 58.99(10)
O4 C11 C10 58.31(10)
O4 C11 C12 117.26(13)
C10 C11 C12 121.84(14)
C4 O1 C7 116.74(14)
C5 O2 C8 116.84(13)
C10 O4 C11 62.71(10)
C16 O5 C18 117.05(13)
C17 O6 C19 120.29(12)
C19 O7 C23 114.72(12)
C2 C1 C6 119.37(14)
C2 C1 C9 123.25(13)
C6 C1 C9 117.38(13)
C1 C2 C3 120.67(14)
C1 C2 H2 119.7
C3 C2 H2 119.7
C4 C3 C2 119.92(14)
C4 C3 H3 120.0
C2 C3 H3 120.0
O1 C4 C3 124.68(14)
O1 C4 C5 115.52(13)
C3 C4 C5 119.80(14)
O2 C5 C6 125.19(14)
O2 C5 C4 115.06(13)
C6 C5 C4 119.75(13)
C5 C6 C1 120.41(14)
C5 C6 H6 119.8
C1 C6 H6 119.8
O1 C7 H7A 109.5
O1 C7 H7B 109.5
H7A C7 H7B 109.5
O1 C7 H7C 109.5
H7A C7 H7C 109.5
H7B C7 H7C 109.5
O2 C8 H8A 109.5
O2 C8 H8B 109.5
H8A C8 H8B 109.5
O2 C8 H8C 109.5
H8A C8 H8C 109.5
H8B C8 H8C 109.5
C11 C10 C9 115.84(14)
O4 C10 H10 117.8
C11 C10 H10 117.8
C9 C10 H10 117.8
O4 C11 H11 115.7
C10 C11 H11 115.7
C12 C11 H11 115.7
C17 C12 C13 120.69(14)
C17 C12 C11 118.13(13)
C13 C12 C11 121.18(14)
C14 C13 C12 119.32(16)
C14 C13 H13 120.3
C12 C13 H13 120.3
C13 C14 C15 120.44(15)
C13 C14 H14 119.8
C15 C14 H14 119.8
C14 C15 C16 120.77(15)
C14 C15 H15 119.6
C16 C15 H15 119.6
O5 C16 C15 124.13(15)
O5 C16 C17 116.94(13)
C15 C16 C17 118.91(14)
O6 C17 C12 115.74(13)
O6 C17 C16 124.33(14)
C12 C17 C16 119.82(13)
O5 C18 H18A 109.5
O5 C18 H18B 109.5
H18A C18 H18B 109.5
O5 C18 H18C 109.5
H18A C18 H18C 109.5
H18B C18 H18C 109.5
O7 C19 O6 111.38(12)
O7 C19 C20 113.84(13)
O6 C19 C20 105.17(12)
O7 C19 H19 108.8
O6 C19 H19 108.8
C20 C19 H19 108.8
C21 C20 C19 111.80(12)
C21 C20 H20A 109.3
C19 C20 H20A 109.3
C21 C20 H20B 109.3
C19 C20 H20B 109.3
H20A C20 H20B 107.9
C20 C21 C22 108.97(12)
C20 C21 H21A 109.9
C22 C21 H21A 109.9
C20 C21 H21B 109.9
C22 C21 H21B 109.9
H21A C21 H21B 108.3
C23 C22 C21 109.50(13)
C23 C22 H22A 109.8
C21 C22 H22A 109.8
C23 C22 H22B 109.8
C21 C22 H22B 109.8
H22A C22 H22B 108.2
O7 C23 C22 111.92(13)
O7 C23 H23A 109.2
C22 C23 H23A 109.2
O7 C23 H23B 109.2
C22 C23 H23B 109.2
H23A C23 H23B 107.9
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
C1 C9 1.483(2)
O3 C9 1.215(2)
C9 C10 1.504(2)
C10 C11 1.489(2)
O4 C10 1.4256(19)
O4 C11 1.4359(19)
C11 C12 1.483(2)
O1 C4 1.3574(19)
O1 C7 1.438(2)
O2 C5 1.3598(18)
O2 C8 1.429(2)
O5 C16 1.366(2)
O5 C18 1.430(2)
O6 C17 1.3746(17)
O6 C19 1.4505(18)
O7 C19 1.4042(19)
O7 C23 1.440(2)
C1 C2 1.390(2)
C1 C6 1.407(2)
C2 C3 1.395(2)
C2 H2 0.9500
C3 C4 1.386(2)
C3 H3 0.9500
C4 C5 1.419(2)
C5 C6 1.378(2)
C6 H6 0.9500
C7 H7A 0.9800
C7 H7B 0.9800
C7 H7C 0.9800
C8 H8A 0.9800
C8 H8B 0.9800
C8 H8C 0.9800
C10 H10 1.0000
C11 H11 1.0000
C12 C17 1.395(2)
C12 C13 1.401(2)
C13 C14 1.384(3)
C13 H13 0.9500
C14 C15 1.397(3)
C14 H14 0.9500
C15 C16 1.395(2)
C15 H15 0.9500
C16 C17 1.409(2)
C18 H18A 0.9800
C18 H18B 0.9800
C18 H18C 0.9800
C19 C20 1.514(2)
C19 H19 1.0000
C20 C21 1.521(2)
C20 H20A 0.9900
C20 H20B 0.9900
C21 C22 1.522(2)
C21 H21A 0.9900
C21 H21B 0.9900
C22 C23 1.519(2)
C22 H22A 0.9900
C22 H22B 0.9900
C23 H23A 0.9900
C23 H23B 0.9900
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 -2.5(2)
C9 C1 C2 C3 177.72(15)
C1 C2 C3 C4 1.2(2)
C7 O1 C4 C3 6.8(2)
C7 O1 C4 C5 -173.40(15)
C2 C3 C4 O1 -178.78(16)
C2 C3 C4 C5 1.4(2)
C8 O2 C5 C6 -2.8(2)
C8 O2 C5 C4 176.94(15)
O1 C4 C5 O2 -2.3(2)
C3 C4 C5 O2 177.56(16)
O1 C4 C5 C6 177.49(15)
C3 C4 C5 C6 -2.7(2)
O2 C5 C6 C1 -178.91(15)
C4 C5 C6 C1 1.4(2)
C2 C1 C6 C5 1.2(2)
C9 C1 C6 C5 -179.00(14)
C2 C1 C9 O3 -166.56(16)
C6 C1 C9 O3 13.6(2)
C2 C1 C9 C10 17.7(2)
C6 C1 C9 C10 -162.10(13)
C11 O4 C10 C9 -106.02(15)
O3 C9 C10 O4 13.8(2)
C1 C9 C10 O4 -170.34(13)
O3 C9 C10 C11 -52.4(2)
C1 C9 C10 C11 123.41(15)
C10 O4 C11 C12 -112.29(15)
C9 C10 C11 O4 105.60(15)
O4 C10 C11 C12 104.49(16)
C9 C10 C11 C12 -149.91(13)
O4 C11 C12 C17 -170.46(13)
C10 C11 C12 C17 121.61(16)
O4 C11 C12 C13 9.1(2)
C10 C11 C12 C13 -58.8(2)
C17 C12 C13 C14 0.4(2)
C11 C12 C13 C14 -179.17(15)
C12 C13 C14 C15 0.9(3)
C13 C14 C15 C16 -0.6(3)
C18 O5 C16 C15 1.3(2)
C18 O5 C16 C17 179.94(14)
C14 C15 C16 O5 177.70(15)
C14 C15 C16 C17 -0.9(2)
C19 O6 C17 C12 -136.15(14)
C19 O6 C17 C16 47.8(2)
C13 C12 C17 O6 -178.22(14)
C11 C12 C17 O6 1.37(19)
C13 C12 C17 C16 -1.9(2)
C11 C12 C17 C16 177.65(13)
O5 C16 C17 O6 -0.6(2)
C15 C16 C17 O6 178.13(14)
O5 C16 C17 C12 -176.55(13)
C15 C16 C17 C12 2.2(2)
C23 O7 C19 O6 67.84(16)
C23 O7 C19 C20 -50.85(17)
C17 O6 C19 O7 39.66(18)
C17 O6 C19 C20 163.43(12)
O7 C19 C20 C21 50.31(18)
O6 C19 C20 C21 -71.88(15)
C19 C20 C21 C22 -52.97(17)
C20 C21 C22 C23 56.24(17)
C19 O7 C23 C22 54.54(17)
C21 C22 C23 O7 -57.01(17)
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 9081014
