#------------------------------------------------------------------------------
#$Date: 2017-10-13 11:42:48 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201978 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/22/07/2220700.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_2220700
loop_
_publ_author_name
'Tang, Ting'
'Gao, Lei'
'Jia, Hong-Sheng'
'Wu, Ya-Ming'
'Ma, Hong-Fei'
_publ_section_title
;
 Ethyl 1-[(4-acetyl-2-methoxyphenoxy)methyl]cyclopropane-1-carboxylate
;
_journal_coeditor_code           BH2213
_journal_issue                   2
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o305
_journal_paper_doi               10.1107/S1600536809000956
_journal_volume                  65
_journal_year                    2009
_chemical_formula_iupac          'C16 H20 O5'
_chemical_formula_moiety         'C16 H20 O5'
_chemical_formula_sum            'C16 H20 O5'
_chemical_formula_weight         292.32
_chemical_name_systematic
;
Ethyl 1-[(4-acetyl-2-methoxyphenoxy)methyl]cyclopropane-1-carboxylate
;
_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   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 107.25(3)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   12.663(3)
_cell_length_b                   8.5020(17)
_cell_length_c                   14.676(3)
_cell_measurement_reflns_used    25
_cell_measurement_temperature    298(2)
_cell_measurement_theta_max      13
_cell_measurement_theta_min      9
_cell_volume                     1509.0(6)
_computing_cell_refinement       'CAD-4 Software (Enraf--Nonius, 1985)'
_computing_data_collection       'CAD-4 Software (Enraf--Nonius, 1985)'
_computing_data_reduction        'XCAD4 (Harms & Wocadlo, 1995)'
_computing_molecular_graphics    'SHELXTL (Sheldrick, 2008)'
_computing_publication_material  'SHELXTL (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      298(2)
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measurement_device_type  'Enraf--Nonius CAD-4'
_diffrn_measurement_method       ω/2θ
_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  0.0391
_diffrn_reflns_av_sigmaI/netI    0.0647
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       0
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       0
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            2874
_diffrn_reflns_theta_full        25.27
_diffrn_reflns_theta_max         25.27
_diffrn_reflns_theta_min         1.68
_diffrn_standards_decay_%        1
_diffrn_standards_interval_count 200
_diffrn_standards_interval_time  120
_diffrn_standards_number         3
_exptl_absorpt_coefficient_mu    0.095
_exptl_absorpt_correction_T_max  0.9905
_exptl_absorpt_correction_T_min  0.9812
_exptl_absorpt_correction_type   psi-scan
_exptl_absorpt_process_details   '(North et al.,  1968)'
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.287
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             624
_exptl_crystal_size_max          0.20
_exptl_crystal_size_mid          0.10
_exptl_crystal_size_min          0.10
_refine_diff_density_max         0.216
_refine_diff_density_min         -0.202
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.926
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_constraints    0
_refine_ls_number_parameters     193
_refine_ls_number_reflns         2732
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.926
_refine_ls_R_factor_all          0.1270
_refine_ls_R_factor_gt           0.0618
_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)+(0.06P)²+1.15P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1314
_refine_ls_wR_factor_ref         0.1679
_reflns_number_gt                1473
_reflns_number_total             2732
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            bh2213.cif
_cod_data_source_block           I
_cod_original_cell_volume        1509.0(5)
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               2220700
_cod_database_fobs_code          2220700
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_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 0.5800(2) 0.2003(4) 0.7367(2) 0.0809(10) Uani d . 1 . .
C C1 0.7006(3) 0.3398(5) 0.6698(3) 0.0673(13) Uani d . 1 . .
H H1A 0.7445 0.3495 0.7353 0.101 Uiso calc R 1 . .
H H1B 0.6823 0.4426 0.6428 0.101 Uiso calc R 1 . .
H H1C 0.7418 0.2838 0.6348 0.101 Uiso calc R 1 . .
O O2 0.26250(19) -0.0087(3) 0.46428(15) 0.0472(6) Uani d . 1 . .
C C2 0.5977(3) 0.2525(5) 0.6646(3) 0.0522(10) Uani d . 1 . .
O O3 0.27923(17) 0.1243(3) 0.31287(15) 0.0431(6) Uani d . 1 . .
C C3 0.5143(3) 0.2248(4) 0.5700(2) 0.0403(8) Uani d . 1 . .
O O4 0.1020(2) 0.3513(3) 0.20147(19) 0.0602(8) Uani d . 1 . .
C C4 0.4262(3) 0.1219(4) 0.5639(2) 0.0417(9) Uani d . 1 . .
H H4A 0.4197 0.0740 0.6189 0.050 Uiso calc R 1 . .
C C5 0.3492(3) 0.0907(4) 0.4776(2) 0.0360(8) Uani d . 1 . .
O O5 -0.0032(2) 0.2019(4) 0.0853(2) 0.0883(11) Uani d . 1 . .
C C6 0.3593(3) 0.1627(4) 0.3945(2) 0.0375(8) Uani d . 1 . .
C C7 0.4462(3) 0.2622(4) 0.3995(2) 0.0415(9) Uani d . 1 . .
H H7A 0.4534 0.3086 0.3442 0.050 Uiso calc R 1 . .
C C8 0.5237(3) 0.2938(4) 0.4871(3) 0.0464(9) Uani d . 1 . .
H H8A 0.5823 0.3616 0.4901 0.056 Uiso calc R 1 . .
C C9 0.2450(3) -0.0810(5) 0.5458(3) 0.0565(11) Uani d . 1 . .
H H9A 0.1861 -0.1562 0.5259 0.085 Uiso calc R 1 . .
H H9B 0.2256 -0.0022 0.5849 0.085 Uiso calc R 1 . .
H H9C 0.3115 -0.1334 0.5817 0.085 Uiso calc R 1 . .
C C10 0.2902(3) 0.1857(4) 0.2248(2) 0.0413(9) Uani d . 1 . .
H H10A 0.3545 0.1404 0.2118 0.050 Uiso calc R 1 . .
H H10B 0.2994 0.2990 0.2292 0.050 Uiso calc R 1 . .
C C11 0.1888(3) 0.1450(4) 0.1471(2) 0.0414(8) Uani d . 1 . .
C C12 0.1746(3) -0.0231(5) 0.1132(3) 0.0567(11) Uani d . 1 . .
H H12A 0.2312 -0.0979 0.1453 0.068 Uiso calc R 1 . .
H H12B 0.1001 -0.0653 0.0930 0.068 Uiso calc R 1 . .
C C13 0.2038(3) 0.0959(5) 0.0513(2) 0.0590(11) Uani d . 1 . .
H H13A 0.1471 0.1268 -0.0064 0.071 Uiso calc R 1 . .
H H13B 0.2784 0.0942 0.0461 0.071 Uiso calc R 1 . .
C C14 0.0850(3) 0.2319(5) 0.1393(3) 0.0497(10) Uani d . 1 . .
C C15 0.0056(4) 0.4466(6) 0.2022(3) 0.0750(14) Uani d . 1 . .
H H15A -0.0610 0.3843 0.1777 0.090 Uiso calc R 1 . .
H H15B 0.0113 0.4756 0.2675 0.090 Uiso calc R 1 . .
C C16 -0.0033(4) 0.5888(6) 0.1448(4) 0.0806(14) Uani d . 1 . .
H H16A -0.0661 0.6490 0.1485 0.121 Uiso calc R 1 . .
H H16B -0.0123 0.5605 0.0797 0.121 Uiso calc R 1 . .
H H16C 0.0626 0.6506 0.1687 0.121 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 0.0016 '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_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle
_geom_angle_publ_flag
C2 C1 H1A . . 109.5 ?
C2 C1 H1B . . 109.5 ?
H1A C1 H1B . . 109.5 ?
C2 C1 H1C . . 109.5 ?
H1A C1 H1C . . 109.5 ?
H1B C1 H1C . . 109.5 ?
C5 O2 C9 . . 118.1(3) ?
O1 C2 C1 . . 121.3(3) ?
O1 C2 C3 . . 119.0(4) ?
C1 C2 C3 . . 119.7(4) ?
C6 O3 C10 . . 117.3(2) ?
C8 C3 C4 . . 118.9(3) ?
C8 C3 C2 . . 121.8(3) ?
C4 C3 C2 . . 119.3(3) ?
C14 O4 C15 . . 117.2(3) ?
C5 C4 C3 . . 120.9(3) ?
C5 C4 H4A . . 119.5 ?
C3 C4 H4A . . 119.5 ?
O2 C5 C4 . . 125.3(3) ?
O2 C5 C6 . . 115.2(3) ?
C4 C5 C6 . . 119.5(3) ?
O3 C6 C7 . . 124.9(3) ?
O3 C6 C5 . . 115.1(3) ?
C7 C6 C5 . . 120.0(3) ?
C6 C7 C8 . . 120.1(3) ?
C6 C7 H7A . . 119.9 ?
C8 C7 H7A . . 119.9 ?
C3 C8 C7 . . 120.5(3) ?
C3 C8 H8A . . 119.7 ?
C7 C8 H8A . . 119.7 ?
O2 C9 H9A . . 109.5 ?
O2 C9 H9B . . 109.5 ?
H9A C9 H9B . . 109.5 ?
O2 C9 H9C . . 109.5 ?
H9A C9 H9C . . 109.5 ?
H9B C9 H9C . . 109.5 ?
O3 C10 C11 . . 108.3(3) ?
O3 C10 H10A . . 110.0 ?
C11 C10 H10A . . 110.0 ?
O3 C10 H10B . . 110.0 ?
C11 C10 H10B . . 110.0 ?
H10A C10 H10B . . 108.4 ?
C14 C11 C10 . . 119.3(3) ?
C14 C11 C12 . . 115.5(3) ?
C10 C11 C12 . . 117.9(3) ?
C14 C11 C13 . . 114.4(3) ?
C10 C11 C13 . . 117.0(3) ?
C12 C11 C13 . . 58.2(2) ?
C13 C12 C11 . . 61.7(2) ?
C13 C12 H12A . . 117.6 ?
C11 C12 H12A . . 117.6 ?
C13 C12 H12B . . 117.6 ?
C11 C12 H12B . . 117.6 ?
H12A C12 H12B . . 114.7 ?
C12 C13 C11 . . 60.0(2) ?
C12 C13 H13A . . 117.8 ?
C11 C13 H13A . . 117.8 ?
C12 C13 H13B . . 117.8 ?
C11 C13 H13B . . 117.8 ?
H13A C13 H13B . . 114.9 ?
O5 C14 O4 . . 123.1(4) ?
O5 C14 C11 . . 125.5(4) ?
O4 C14 C11 . . 111.4(3) ?
C16 C15 O4 . . 112.0(4) ?
C16 C15 H15A . . 109.2 ?
O4 C15 H15A . . 109.2 ?
C16 C15 H15B . . 109.2 ?
O4 C15 H15B . . 109.2 ?
H15A C15 H15B . . 107.9 ?
C15 C16 H16A . . 109.5 ?
C15 C16 H16B . . 109.5 ?
H16A C16 H16B . . 109.5 ?
C15 C16 H16C . . 109.5 ?
H16A C16 H16C . . 109.5 ?
H16B C16 H16C . . 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 C2 . 1.227(4) ?
C1 C2 . 1.482(5) ?
C1 H1A . 0.9600 ?
C1 H1B . 0.9600 ?
C1 H1C . 0.9600 ?
O2 C5 . 1.352(4) ?
O2 C9 . 1.419(4) ?
C2 C3 . 1.493(5) ?
O3 C6 . 1.360(3) ?
O3 C10 . 1.438(4) ?
C3 C8 . 1.387(5) ?
C3 C4 . 1.399(5) ?
O4 C14 . 1.339(4) ?
O4 C15 . 1.468(4) ?
C4 C5 . 1.376(4) ?
C4 H4A . 0.9300 ?
C5 C6 . 1.405(5) ?
O5 C14 . 1.189(4) ?
C6 C7 . 1.373(4) ?
C7 C8 . 1.393(5) ?
C7 H7A . 0.9300 ?
C8 H8A . 0.9300 ?
C9 H9A . 0.9600 ?
C9 H9B . 0.9600 ?
C9 H9C . 0.9600 ?
C10 C11 . 1.483(4) ?
C10 H10A . 0.9700 ?
C10 H10B . 0.9700 ?
C11 C14 . 1.482(5) ?
C11 C12 . 1.506(5) ?
C11 C13 . 1.532(5) ?
C12 C13 . 1.478(5) ?
C12 H12A . 0.9700 ?
C12 H12B . 0.9700 ?
C13 H13A . 0.9700 ?
C13 H13B . 0.9700 ?
C15 C16 . 1.459(6) ?
C15 H15A . 0.9700 ?
C15 H15B . 0.9700 ?
C16 H16A . 0.9600 ?
C16 H16B . 0.9600 ?
C16 H16C . 0.9600 ?
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
C7 H7A O1 4_565 0.9300 2.5600 3.329(4) 140.00 yes
C15 H15A O5 . 0.9700 2.3200 2.678(6) 101.00 no
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
O1 C2 C3 C8 . . . . 173.4(4) ?
C1 C2 C3 C8 . . . . -7.6(5) ?
O1 C2 C3 C4 . . . . -9.0(5) ?
C1 C2 C3 C4 . . . . 170.0(3) ?
C8 C3 C4 C5 . . . . -0.8(5) ?
C2 C3 C4 C5 . . . . -178.5(3) ?
C9 O2 C5 C4 . . . . 3.6(5) ?
C9 O2 C5 C6 . . . . -177.7(3) ?
C3 C4 C5 O2 . . . . 178.9(3) ?
C3 C4 C5 C6 . . . . 0.2(5) ?
C10 O3 C6 C7 . . . . 3.6(5) ?
C10 O3 C6 C5 . . . . -175.5(3) ?
O2 C5 C6 O3 . . . . 1.2(4) ?
C4 C5 C6 O3 . . . . 179.9(3) ?
O2 C5 C6 C7 . . . . -178.1(3) ?
C4 C5 C6 C7 . . . . 0.7(5) ?
O3 C6 C7 C8 . . . . 179.9(3) ?
C5 C6 C7 C8 . . . . -1.0(5) ?
C4 C3 C8 C7 . . . . 0.6(5) ?
C2 C3 C8 C7 . . . . 178.2(3) ?
C6 C7 C8 C3 . . . . 0.3(5) ?
C6 O3 C10 C11 . . . . -173.7(3) ?
O3 C10 C11 C14 . . . . 74.4(4) ?
O3 C10 C11 C12 . . . . -74.2(4) ?
O3 C10 C11 C13 . . . . -140.7(3) ?
C14 C11 C12 C13 . . . . 104.1(4) ?
C10 C11 C12 C13 . . . . -106.1(4) ?
C14 C11 C13 C12 . . . . -106.0(4) ?
C10 C11 C13 C12 . . . . 107.5(4) ?
C15 O4 C14 O5 . . . . 0.7(6) ?
C15 O4 C14 C11 . . . . -179.3(3) ?
C10 C11 C14 O5 . . . . -173.6(4) ?
C12 C11 C14 O5 . . . . -24.2(6) ?
C13 C11 C14 O5 . . . . 40.7(5) ?
C10 C11 C14 O4 . . . . 6.4(5) ?
C12 C11 C14 O4 . . . . 155.8(3) ?
C13 C11 C14 O4 . . . . -139.3(3) ?
C14 O4 C15 C16 . . . . -96.6(4) ?
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 24741558
