#------------------------------------------------------------------------------
#$Date: 2017-10-13 11:42:48 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201978 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/22/12/2221224.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_2221224
loop_
_publ_author_name
'Yan, Shi-qiang'
'Liang, Xiao-mei'
'Zhang, Jian-jun'
'Wang, Dao-quan'
_publ_section_title
;
 2-(4-Methoxyphenoxy)-6-methyl-3-oxo-3,6-dihydro-2H-pyran-4-yl
 benzoate
;
_journal_coeditor_code           XU2467
_journal_issue                   3
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o586
_journal_paper_doi               10.1107/S1600536809004231
_journal_volume                  65
_journal_year                    2009
_chemical_formula_iupac          'C20 H18 O6'
_chemical_formula_moiety         'C20 H18 O6'
_chemical_formula_sum            'C20 H18 O6'
_chemical_formula_weight         354.34
_chemical_name_systematic
;
2-(4-Methoxyphenoxy)-6-methyl-3-oxo-3,6-dihydro-2H-pyran-4-yl benzoate
;
_space_group_IT_number           19
_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_Hall  'P 2ac 2ab'
_symmetry_space_group_name_H-M   'P 21 21 21'
_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                 90.00
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   8.5906(17)
_cell_length_b                   11.594(2)
_cell_length_c                   17.404(4)
_cell_measurement_reflns_used    789
_cell_measurement_temperature    173(2)
_cell_measurement_theta_max      27.48
_cell_measurement_theta_min      2.17
_cell_volume                     1733.4(6)
_computing_cell_refinement       'RAPID-AUTO (Rigaku, 2001)'
_computing_data_collection       'RAPID-AUTO (Rigaku, 2001)'
_computing_data_reduction        'RAPID-AUTO (Rigaku, 2001)'
_computing_molecular_graphics    'SHELXTL (Sheldrick, 2008)'
_computing_publication_material  'SHELXTL (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXTL (Sheldrick, 2008)'
_computing_structure_solution    'SHELXTL (Sheldrick, 2008)'
_diffrn_ambient_temperature      173(2)
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_device_type  'Rigaku R-Axis Rapid IP are-detector'
_diffrn_measurement_method       'ω scan'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'rotating anode'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0154
_diffrn_reflns_av_sigmaI/netI    0.0708
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_number            3953
_diffrn_reflns_theta_full        27.44
_diffrn_reflns_theta_max         27.44
_diffrn_reflns_theta_min         2.11
_diffrn_standards_interval_count 0
_diffrn_standards_interval_time  0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.101
_exptl_absorpt_correction_T_max  0.961
_exptl_absorpt_correction_T_min  0.924
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(ABSCOR; Higashi, 1995)'
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.358
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             744
_exptl_crystal_size_max          0.80
_exptl_crystal_size_mid          0.72
_exptl_crystal_size_min          0.40
_refine_diff_density_max         0.173
_refine_diff_density_min         -0.243
_refine_ls_extinction_coef       0.0215(13)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_ref   0.867
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     236
_refine_ls_number_reflns         2262
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.867
_refine_ls_R_factor_all          0.0595
_refine_ls_R_factor_gt           0.0342
_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)]'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0503
_refine_ls_wR_factor_ref         0.0548
_reflns_number_gt                1752
_reflns_number_total             2262
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            xu2467.cif
_cod_data_source_block           I
_cod_database_code               2221224
_cod_database_fobs_code          2221224
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'-x, y+1/2, -z+1/2'
'x+1/2, -y+1/2, -z'
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
_atom_site_disorder_assembly
_atom_site_disorder_group
O O1 1.17184(15) 0.59200(11) 0.94630(8) 0.0262(4) Uani d . 1 . .
O O2 0.93224(17) 0.89681(11) 0.91264(8) 0.0298(4) Uani d . 1 . .
O O3 1.04268(19) 0.94639(12) 1.02536(9) 0.0370(4) Uani d . 1 . .
O O4 1.21198(18) 0.84659(12) 0.84053(9) 0.0372(4) Uani d . 1 . .
O O5 1.13746(15) 0.59345(11) 0.81269(7) 0.0230(3) Uani d . 1 . .
O O6 1.36640(18) 0.16881(11) 0.72242(9) 0.0371(4) Uani d . 1 . .
C C1 1.0087(2) 0.58644(17) 0.96426(13) 0.0278(5) Uani d . 1 . .
H H1A 0.9575 0.5302 0.9288 0.033 Uiso calc R 1 . .
C C2 0.9327(3) 0.70107(17) 0.95530(12) 0.0290(5) Uani d . 1 . .
H H2A 0.8318 0.7123 0.9763 0.035 Uiso calc R 1 . .
C C3 1.0009(3) 0.78794(17) 0.91900(12) 0.0257(5) Uani d . 1 . .
C C4 1.1459(2) 0.77091(16) 0.87611(12) 0.0250(5) Uani d . 1 . .
C C5 1.2071(2) 0.64760(16) 0.87719(11) 0.0236(5) Uani d . 1 . .
H H5A 1.3226 0.6488 0.8701 0.028 Uiso calc R 1 . .
C C6 0.9976(3) 0.5411(2) 1.04592(14) 0.0425(6) Uani d . 1 . .
H H6A 1.0486 0.4657 1.0491 0.064 Uiso calc R 1 . .
H H6B 0.8878 0.5333 1.0604 0.064 Uiso calc R 1 . .
H H6C 1.0491 0.5952 1.0810 0.064 Uiso calc R 1 . .
C C7 0.9639(2) 0.97192(17) 0.97094(13) 0.0251(5) Uani d . 1 . .
C C8 0.8888(2) 1.08488(16) 0.95760(12) 0.0230(5) Uani d . 1 . .
C C9 0.8571(3) 1.15548(17) 1.02010(13) 0.0304(5) Uani d . 1 . .
H H9A 0.8852 1.1316 1.0705 0.037 Uiso calc R 1 . .
C C10 0.7844(3) 1.26088(18) 1.00880(15) 0.0379(6) Uani d . 1 . .
H H10A 0.7621 1.3092 1.0515 0.045 Uiso calc R 1 . .
C C11 0.7445(3) 1.29565(18) 0.93534(14) 0.0384(6) Uani d . 1 . .
H H11A 0.6946 1.3679 0.9277 0.046 Uiso calc R 1 . .
C C12 0.7767(3) 1.22605(17) 0.87332(14) 0.0340(6) Uani d . 1 . .
H H12A 0.7498 1.2507 0.8230 0.041 Uiso calc R 1 . .
C C13 0.8478(2) 1.12062(16) 0.88406(12) 0.0278(5) Uani d . 1 . .
H H13A 0.8687 1.0724 0.8412 0.033 Uiso calc R 1 . .
C C14 1.1981(2) 0.48407(16) 0.79498(10) 0.0203(5) Uani d . 1 . .
C C15 1.3486(2) 0.47295(16) 0.76804(11) 0.0242(5) Uani d . 1 . .
H H15A 1.4147 0.5385 0.7652 0.029 Uiso calc R 1 . .
C C16 1.4024(2) 0.36583(16) 0.74524(12) 0.0260(5) Uani d . 1 . .
H H16A 1.5060 0.3573 0.7271 0.031 Uiso calc R 1 . .
C C17 1.3043(2) 0.27089(16) 0.74899(12) 0.0247(5) Uani d . 1 . .
C C18 1.1540(3) 0.28231(17) 0.77601(12) 0.0278(5) Uani d . 1 . .
H H18A 1.0869 0.2173 0.7784 0.033 Uiso calc R 1 . .
C C19 1.1018(2) 0.39045(16) 0.79972(11) 0.0260(5) Uani d . 1 . .
H H19A 0.9992 0.3991 0.8192 0.031 Uiso calc R 1 . .
C C20 1.2665(3) 0.07108(16) 0.72123(15) 0.0446(7) Uani d . 1 . .
H H20A 1.3233 0.0044 0.7010 0.067 Uiso calc R 1 . .
H H20B 1.1765 0.0871 0.6883 0.067 Uiso calc R 1 . .
H H20C 1.2307 0.0544 0.7735 0.067 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_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle
_geom_angle_publ_flag
C5 O1 C1 . . 114.77(15) ?
C7 O2 C3 . . 115.67(16) ?
C14 O5 C5 . . 114.64(14) ?
C17 O6 C20 . . 117.11(17) ?
O1 C1 C2 . . 111.40(17) ?
O1 C1 C6 . . 106.29(18) ?
C2 C1 C6 . . 112.29(19) ?
O1 C1 H1A . . 108.9 ?
C2 C1 H1A . . 108.9 ?
C6 C1 H1A . . 108.9 ?
C3 C2 C1 . . 122.3(2) ?
C3 C2 H2A . . 118.9 ?
C1 C2 H2A . . 118.9 ?
C2 C3 O2 . . 122.5(2) ?
C2 C3 C4 . . 121.08(19) ?
O2 C3 C4 . . 116.11(18) ?
O4 C4 C3 . . 124.03(19) ?
O4 C4 C5 . . 121.5(2) ?
C3 C4 C5 . . 114.42(18) ?
O1 C5 O5 . . 112.68(15) ?
O1 C5 C4 . . 111.63(17) ?
O5 C5 C4 . . 105.08(15) ?
O1 C5 H5A . . 109.1 ?
O5 C5 H5A . . 109.1 ?
C4 C5 H5A . . 109.1 ?
C1 C6 H6A . . 109.5 ?
C1 C6 H6B . . 109.5 ?
H6A C6 H6B . . 109.5 ?
C1 C6 H6C . . 109.5 ?
H6A C6 H6C . . 109.5 ?
H6B C6 H6C . . 109.5 ?
O3 C7 O2 . . 122.79(19) ?
O3 C7 C8 . . 126.03(19) ?
O2 C7 C8 . . 111.18(18) ?
C9 C8 C13 . . 119.72(19) ?
C9 C8 C7 . . 119.00(19) ?
C13 C8 C7 . . 121.27(18) ?
C10 C9 C8 . . 119.8(2) ?
C10 C9 H9A . . 120.1 ?
C8 C9 H9A . . 120.1 ?
C11 C10 C9 . . 120.0(2) ?
C11 C10 H10A . . 120.0 ?
C9 C10 H10A . . 120.0 ?
C12 C11 C10 . . 120.3(2) ?
C12 C11 H11A . . 119.9 ?
C10 C11 H11A . . 119.9 ?
C11 C12 C13 . . 120.2(2) ?
C11 C12 H12A . . 119.9 ?
C13 C12 H12A . . 119.9 ?
C12 C13 C8 . . 120.1(2) ?
C12 C13 H13A . . 120.0 ?
C8 C13 H13A . . 120.0 ?
C19 C14 C15 . . 120.83(18) ?
C19 C14 O5 . . 118.64(18) ?
C15 C14 O5 . . 120.37(17) ?
C14 C15 C16 . . 119.60(18) ?
C14 C15 H15A . . 120.2 ?
C16 C15 H15A . . 120.2 ?
C15 C16 C17 . . 119.73(19) ?
C15 C16 H16A . . 120.1 ?
C17 C16 H16A . . 120.1 ?
O6 C17 C18 . . 123.95(19) ?
O6 C17 C16 . . 115.51(19) ?
C18 C17 C16 . . 120.52(18) ?
C17 C18 C19 . . 119.18(19) ?
C17 C18 H18A . . 120.4 ?
C19 C18 H18A . . 120.4 ?
C14 C19 C18 . . 120.1(2) ?
C14 C19 H19A . . 119.9 ?
C18 C19 H19A . . 119.9 ?
O6 C20 H20A . . 109.5 ?
O6 C20 H20B . . 109.5 ?
H20A C20 H20B . . 109.5 ?
O6 C20 H20C . . 109.5 ?
H20A C20 H20C . . 109.5 ?
H20B C20 H20C . . 109.5 ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_site_symmetry_2
_geom_bond_distance
_geom_bond_publ_flag
O1 C5 . 1.398(2) ?
O1 C1 . 1.437(2) ?
O2 C7 . 1.365(2) ?
O2 C3 . 1.398(2) ?
O3 C7 . 1.201(2) ?
O4 C4 . 1.215(2) ?
O5 C14 . 1.405(2) ?
O5 C5 . 1.418(2) ?
O6 C17 . 1.378(2) ?
O6 C20 . 1.422(2) ?
C1 C2 . 1.489(3) ?
C1 C6 . 1.518(3) ?
C1 H1A . 1.0000 ?
C2 C3 . 1.326(3) ?
C2 H2A . 0.9500 ?
C3 C4 . 1.465(3) ?
C4 C5 . 1.523(3) ?
C5 H5A . 1.0000 ?
C6 H6A . 0.9800 ?
C6 H6B . 0.9800 ?
C6 H6C . 0.9800 ?
C7 C8 . 1.478(3) ?
C8 C9 . 1.388(3) ?
C8 C13 . 1.391(3) ?
C9 C10 . 1.386(3) ?
C9 H9A . 0.9500 ?
C10 C11 . 1.384(3) ?
C10 H10A . 0.9500 ?
C11 C12 . 1.376(3) ?
C11 H11A . 0.9500 ?
C12 C13 . 1.379(3) ?
C12 H12A . 0.9500 ?
C13 H13A . 0.9500 ?
C14 C19 . 1.367(3) ?
C14 C15 . 1.381(3) ?
C15 C16 . 1.383(3) ?
C15 H15A . 0.9500 ?
C16 C17 . 1.387(3) ?
C16 H16A . 0.9500 ?
C17 C18 . 1.381(3) ?
C18 C19 . 1.394(3) ?
C18 H18A . 0.9500 ?
C19 H19A . 0.9500 ?
C20 H20A . 0.9800 ?
C20 H20B . 0.9800 ?
C20 H20C . 0.9800 ?
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_site_symmetry_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_publ_flag
C15 H15A O6 3_856 0.95 2.42 3.343(2) 163 y
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_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion
_geom_torsion_publ_flag
C5 O1 C1 C2 . . . . -48.6(2) ?
C5 O1 C1 C6 . . . . -171.17(16) ?
O1 C1 C2 C3 . . . . 14.0(3) ?
C6 C1 C2 C3 . . . . 133.1(2) ?
C1 C2 C3 O2 . . . . -177.84(19) ?
C1 C2 C3 C4 . . . . 8.9(3) ?
C7 O2 C3 C2 . . . . 89.0(2) ?
C7 O2 C3 C4 . . . . -97.4(2) ?
C2 C3 C4 O4 . . . . 178.5(2) ?
O2 C3 C4 O4 . . . . 4.8(3) ?
C2 C3 C4 C5 . . . . 0.3(3) ?
O2 C3 C4 C5 . . . . -173.41(17) ?
C1 O1 C5 O5 . . . . -59.9(2) ?
C1 O1 C5 C4 . . . . 58.1(2) ?
C14 O5 C5 O1 . . . . -68.5(2) ?
C14 O5 C5 C4 . . . . 169.78(16) ?
O4 C4 C5 O1 . . . . 149.13(18) ?
C3 C4 C5 O1 . . . . -32.6(2) ?
O4 C4 C5 O5 . . . . -88.4(2) ?
C3 C4 C5 O5 . . . . 89.8(2) ?
C3 O2 C7 O3 . . . . -1.6(3) ?
C3 O2 C7 C8 . . . . 178.67(17) ?
O3 C7 C8 C9 . . . . -23.8(3) ?
O2 C7 C8 C9 . . . . 155.93(18) ?
O3 C7 C8 C13 . . . . 157.1(2) ?
O2 C7 C8 C13 . . . . -23.2(3) ?
C13 C8 C9 C10 . . . . 0.2(3) ?
C7 C8 C9 C10 . . . . -179.0(2) ?
C8 C9 C10 C11 . . . . -0.3(3) ?
C9 C10 C11 C12 . . . . 0.0(4) ?
C10 C11 C12 C13 . . . . 0.6(4) ?
C11 C12 C13 C8 . . . . -0.7(3) ?
C9 C8 C13 C12 . . . . 0.3(3) ?
C7 C8 C13 C12 . . . . 179.49(19) ?
C5 O5 C14 C19 . . . . 116.7(2) ?
C5 O5 C14 C15 . . . . -67.9(2) ?
C19 C14 C15 C16 . . . . 0.3(3) ?
O5 C14 C15 C16 . . . . -174.99(17) ?
C14 C15 C16 C17 . . . . 0.6(3) ?
C20 O6 C17 C18 . . . . 1.8(3) ?
C20 O6 C17 C16 . . . . -176.5(2) ?
C15 C16 C17 O6 . . . . 177.71(17) ?
C15 C16 C17 C18 . . . . -0.6(3) ?
O6 C17 C18 C19 . . . . -178.37(19) ?
C16 C17 C18 C19 . . . . -0.2(3) ?
C15 C14 C19 C18 . . . . -1.1(3) ?
O5 C14 C19 C18 . . . . 174.26(17) ?
C17 C18 C19 C14 . . . . 1.0(3) ?
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 24741707
