#------------------------------------------------------------------------------
#$Date: 2017-10-13 11:42:48 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201978 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/22/04/2220481.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_2220481
loop_
_publ_author_name
'Badshah, Amir'
'Hasan, Aurangzeb'
'Barbarín, Cecilia R.'
'Abbas, Asghar'
'Ali, Sajid'
_publ_section_title
;
 Ethyl
 6-(4-ethoxyphenyl)-4-(furan-2-yl)-2-oxocyclohex-3-ene-1-carboxylate
;
_journal_coeditor_code           FB2116
_journal_issue                   1
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o70
_journal_paper_doi               10.1107/S1600536808040130
_journal_volume                  65
_journal_year                    2009
_chemical_formula_iupac          'C21 H22 O5'
_chemical_formula_moiety         'C21 H22 O5'
_chemical_formula_sum            'C21 H22 O5'
_chemical_formula_weight         354.39
_chemical_melting_point          388
_chemical_name_systematic
;
(1SR,6RS)-Ethyl
6-(4-ethoxyphenyl)-4-(furan-2-yl)-2-oxocyclohex-3-ene-1-carboxylate
;
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2yn'
_symmetry_space_group_name_H-M   'P 1 21/n 1'
_atom_sites_solution_hydrogens   difmap
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 104.07(2)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   7.361(3)
_cell_length_b                   17.350(4)
_cell_length_c                   14.473(3)
_cell_measurement_reflns_used    86
_cell_measurement_temperature    298(2)
_cell_measurement_theta_max      12.90
_cell_measurement_theta_min      4.58
_cell_volume                     1792.9(9)
_computing_cell_refinement       'XSCANS (Siemens, 1999)'
_computing_data_collection       'XSCANS (Siemens, 1999)'
_computing_data_reduction        'XSCANS (Siemens, 1999)'
_computing_molecular_graphics
;
SHELXTL-Plus (Sheldrick, 2008) and Mercury (Macrae et al.,
2006)
;
_computing_publication_material  'SHELXTL-Plus (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXTL-Plus (Sheldrick, 2008)'
_computing_structure_solution    'SHELXTL-Plus (Sheldrick, 2008)'
_diffrn_ambient_temperature      298(2)
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device_type  'Bruker P4'
_diffrn_measurement_method       ω
_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  0.0205
_diffrn_reflns_av_sigmaI/netI    0.0278
_diffrn_reflns_limit_h_max       4
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       1
_diffrn_reflns_limit_k_min       -24
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            8745
_diffrn_reflns_theta_full        29.99
_diffrn_reflns_theta_max         29.99
_diffrn_reflns_theta_min         2.35
_diffrn_standards_decay_%        3.44
_diffrn_standards_interval_count 97
_diffrn_standards_number         3
_exptl_absorpt_coefficient_mu    0.093
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.313
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       Prism
_exptl_crystal_F_000             752
_exptl_crystal_size_max          0.60
_exptl_crystal_size_mid          0.40
_exptl_crystal_size_min          0.40
_refine_diff_density_max         0.272
_refine_diff_density_min         -0.173
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.056
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_constraints    86
_refine_ls_number_parameters     237
_refine_ls_number_reflns         5218
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.056
_refine_ls_R_factor_all          0.0692
_refine_ls_R_factor_gt           0.0473
_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)+(0.057P)²+0.3325P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1208
_refine_ls_wR_factor_ref         0.1349
_reflns_number_gt                3806
_reflns_number_total             5218
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            fb2116.cif
_cod_data_source_block           I
_cod_original_cell_volume        1792.8(9)
_cod_original_sg_symbol_H-M      'P 21/n'
_cod_database_code               2220481
_cod_database_fobs_code          2220481
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -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
_atom_site_disorder_assembly
_atom_site_disorder_group
O O1 -0.07980(14) 0.45302(6) 0.31575(9) 0.0611(3) Uani d . 1 . .
O O2 0.43726(17) 0.45205(7) 0.60674(8) 0.0646(3) Uani d . 1 . .
O O3 0.67391(17) 0.29800(7) 0.65190(8) 0.0627(3) Uani d . 1 . .
O O4 0.86811(14) 0.37514(6) 0.59822(8) 0.0571(3) Uani d . 1 . .
O O5 1.03226(14) 0.08582(5) 0.40318(7) 0.0495(2) Uani d . 1 . .
C C1 -0.2189(2) 0.45660(10) 0.23520(15) 0.0697(5) Uani d . 1 . .
H H1A -0.3227 0.4888 0.2267 0.084 Uiso calc R 1 . .
C C2 -0.1874(2) 0.40812(10) 0.16994(13) 0.0642(4) Uani d . 1 . .
H H2A -0.2628 0.4004 0.1090 0.077 Uiso calc R 1 . .
C C3 -0.0168(2) 0.37048(9) 0.21122(11) 0.0514(3) Uani d . 1 . .
H H3A 0.0416 0.3328 0.1829 0.062 Uiso calc R 1 . .
C C4 0.04471(17) 0.39962(7) 0.29930(10) 0.0439(3) Uani d . 1 . .
C C5 0.21001(17) 0.38693(7) 0.37425(10) 0.0411(3) Uani d . 1 . .
C C6 0.23954(19) 0.42500(8) 0.45737(11) 0.0488(3) Uani d . 1 . .
H H6A 0.1459 0.4574 0.4679 0.059 Uiso calc R 1 . .
C C7 0.4111(2) 0.41770(8) 0.53120(10) 0.0471(3) Uani d . 1 . .
C C8 0.56299(18) 0.36875(7) 0.50669(9) 0.0422(3) Uani d . 1 . .
H H8A 0.6283 0.4004 0.4688 0.051 Uiso calc R 1 . .
C C9 0.47735(17) 0.29939(7) 0.44584(9) 0.0394(3) Uani d . 1 . .
H H9A 0.3986 0.2718 0.4806 0.047 Uiso calc R 1 . .
C C10 0.34964(17) 0.33007(8) 0.35447(9) 0.0415(3) Uani d . 1 . .
H H10A 0.4249 0.3548 0.3165 0.050 Uiso calc R 1 . .
H H10B 0.2835 0.2874 0.3179 0.050 Uiso calc R 1 . .
C C11 0.7048(2) 0.34303(8) 0.59512(9) 0.0457(3) Uani d . 1 . .
C C12 1.0290(2) 0.34644(11) 0.66794(13) 0.0672(5) Uani d . 1 . .
H H12A 0.9931 0.3332 0.7262 0.081 Uiso calc R 1 . .
H H12B 1.1248 0.3860 0.6827 0.081 Uiso calc R 1 . .
C C13 1.1037(3) 0.27755(12) 0.62977(14) 0.0757(5) Uani d . 1 . .
H H13A 1.2236 0.2645 0.6702 0.114 Uiso calc R 1 . .
H H13B 1.1170 0.2882 0.5667 0.114 Uiso calc R 1 . .
H H13C 1.0189 0.2352 0.6277 0.114 Uiso calc R 1 . .
C C14 0.62510(16) 0.24380(7) 0.43058(8) 0.0373(2) Uani d . 1 . .
C C15 0.6367(2) 0.17049(8) 0.46933(10) 0.0454(3) Uani d . 1 . .
H H15A 0.5501 0.1555 0.5031 0.054 Uiso calc R 1 . .
C C16 0.7726(2) 0.11937(8) 0.45920(10) 0.0482(3) Uani d . 1 . .
H H16A 0.7773 0.0705 0.4861 0.058 Uiso calc R 1 . .
C C17 0.90234(17) 0.14023(7) 0.40922(9) 0.0381(3) Uani d . 1 . .
C C18 0.89386(18) 0.21308(7) 0.36978(10) 0.0420(3) Uani d . 1 . .
H H18A 0.9803 0.2279 0.3358 0.050 Uiso calc R 1 . .
C C19 0.75621(18) 0.26366(7) 0.38113(10) 0.0431(3) Uani d . 1 . .
H H19A 0.7518 0.3126 0.3546 0.052 Uiso calc R 1 . .
C C20 1.1525(2) 0.10138(8) 0.34250(11) 0.0516(3) Uani d . 1 . .
H H20A 1.2328 0.1449 0.3665 0.062 Uiso calc R 1 . .
H H20B 1.0795 0.1137 0.2789 0.062 Uiso calc R 1 . .
C C21 1.2679(3) 0.03130(10) 0.33988(16) 0.0721(5) Uani d . 1 . .
H H21A 1.3438 0.0389 0.2953 0.108 Uiso calc R 1 . .
H H21B 1.1871 -0.0122 0.3206 0.108 Uiso calc R 1 . .
H H21C 1.3471 0.0220 0.4021 0.108 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_
_diffrn_standard_refln_index_h
_diffrn_standard_refln_index_k
_diffrn_standard_refln_index_l
1 2 -3
1 3 1
3 7 -5
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
C1 O1 C4 . . 106.29(13) ?
C11 O4 C12 . . 117.70(13) ?
C17 O5 C20 . . 117.53(10) ?
C2 C1 O1 . . 110.96(14) ?
C2 C1 H1A . . 124.5 ?
O1 C1 H1A . . 124.5 ?
C1 C2 C3 . . 106.45(15) ?
C1 C2 H2A . . 126.8 ?
C3 C2 H2A . . 126.8 ?
C4 C3 C2 . . 106.68(15) ?
C4 C3 H3A . . 126.7 ?
C2 C3 H3A . . 126.7 ?
C3 C4 O1 . . 109.60(12) ?
C3 C4 C5 . . 133.38(13) ?
O1 C4 C5 . . 117.00(13) ?
C6 C5 C4 . . 121.59(12) ?
C6 C5 C10 . . 121.65(12) ?
C4 C5 C10 . . 116.75(12) ?
C5 C6 C7 . . 122.71(12) ?
C5 C6 H6A . . 118.6 ?
C7 C6 H6A . . 118.6 ?
O2 C7 C6 . . 122.59(13) ?
O2 C7 C8 . . 121.33(13) ?
C6 C7 C8 . . 115.95(12) ?
C11 C8 C7 . . 111.43(11) ?
C11 C8 C9 . . 110.98(11) ?
C7 C8 C9 . . 110.55(11) ?
C11 C8 H8A . . 107.9 ?
C7 C8 H8A . . 107.9 ?
C9 C8 H8A . . 107.9 ?
C14 C9 C10 . . 114.30(10) ?
C14 C9 C8 . . 112.04(10) ?
C10 C9 C8 . . 107.80(10) ?
C14 C9 H9A . . 107.5 ?
C10 C9 H9A . . 107.5 ?
C8 C9 H9A . . 107.5 ?
C5 C10 C9 . . 111.80(11) ?
C5 C10 H10A . . 109.3 ?
C9 C10 H10A . . 109.3 ?
C5 C10 H10B . . 109.3 ?
C9 C10 H10B . . 109.3 ?
H10A C10 H10B . . 107.9 ?
O3 C11 O4 . . 125.33(13) ?
O3 C11 C8 . . 124.65(14) ?
O4 C11 C8 . . 109.97(12) ?
O4 C12 C13 . . 109.51(13) ?
O4 C12 H12A . . 109.8 ?
C13 C12 H12A . . 109.8 ?
O4 C12 H12B . . 109.8 ?
C13 C12 H12B . . 109.8 ?
H12A C12 H12B . . 108.2 ?
C12 C13 H13A . . 109.5 ?
C12 C13 H13B . . 109.5 ?
H13A C13 H13B . . 109.5 ?
C12 C13 H13C . . 109.5 ?
H13A C13 H13C . . 109.5 ?
H13B C13 H13C . . 109.5 ?
C19 C14 C15 . . 117.27(11) ?
C19 C14 C9 . . 122.46(11) ?
C15 C14 C9 . . 120.24(11) ?
C16 C15 C14 . . 121.73(12) ?
C16 C15 H15A . . 119.1 ?
C14 C15 H15A . . 119.1 ?
C15 C16 C17 . . 120.16(12) ?
C15 C16 H16A . . 119.9 ?
C17 C16 H16A . . 119.9 ?
O5 C17 C16 . . 116.00(11) ?
O5 C17 C18 . . 124.71(11) ?
C16 C17 C18 . . 119.28(11) ?
C19 C18 C17 . . 119.55(12) ?
C19 C18 H18A . . 120.2 ?
C17 C18 H18A . . 120.2 ?
C14 C19 C18 . . 122.01(12) ?
C14 C19 H19A . . 119.0 ?
C18 C19 H19A . . 119.0 ?
O5 C20 C21 . . 107.84(12) ?
O5 C20 H20A . . 110.1 ?
C21 C20 H20A . . 110.1 ?
O5 C20 H20B . . 110.1 ?
C21 C20 H20B . . 110.1 ?
H20A C20 H20B . . 108.5 ?
C20 C21 H21A . . 109.5 ?
C20 C21 H21B . . 109.5 ?
H21A C21 H21B . . 109.5 ?
C20 C21 H21C . . 109.5 ?
H21A C21 H21C . . 109.5 ?
H21B C21 H21C . . 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 C1 . 1.353(2) ?
O1 C4 . 1.3642(16) ?
O2 C7 . 1.2186(17) ?
O3 C11 . 1.1949(18) ?
O4 C11 . 1.3157(18) ?
O4 C12 . 1.4449(18) ?
O5 C17 . 1.3616(15) ?
O5 C20 . 1.4164(17) ?
C1 C2 . 1.327(3) ?
C1 H1A . 0.9300 ?
C2 C3 . 1.413(2) ?
C2 H2A . 0.9300 ?
C3 C4 . 1.344(2) ?
C3 H3A . 0.9300 ?
C4 C5 . 1.4367(19) ?
C5 C6 . 1.343(2) ?
C5 C10 . 1.5015(18) ?
C6 C7 . 1.448(2) ?
C6 H6A . 0.9300 ?
C7 C8 . 1.5133(19) ?
C8 C11 . 1.5090(19) ?
C8 C9 . 1.5334(18) ?
C8 H8A . 0.9800 ?
C9 C14 . 1.5095(17) ?
C9 C10 . 1.5204(18) ?
C9 H9A . 0.9800 ?
C10 H10A . 0.9700 ?
C10 H10B . 0.9700 ?
C12 C13 . 1.478(2) ?
C12 H12A . 0.9700 ?
C12 H12B . 0.9700 ?
C13 H13A . 0.9600 ?
C13 H13B . 0.9600 ?
C13 H13C . 0.9600 ?
C14 C19 . 1.3776(18) ?
C14 C15 . 1.3842(18) ?
C15 C16 . 1.3710(19) ?
C15 H15A . 0.9300 ?
C16 C17 . 1.3791(18) ?
C16 H16A . 0.9300 ?
C17 C18 . 1.3820(17) ?
C18 C19 . 1.3801(18) ?
C18 H18A . 0.9300 ?
C19 H19A . 0.9300 ?
C20 C21 . 1.489(2) ?
C20 H20A . 0.9700 ?
C20 H20B . 0.9700 ?
C21 H21A . 0.9600 ?
C21 H21B . 0.9600 ?
C21 H21C . 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
C3 H3A O3 4_565 0.93 2.55 3.441(2) 160 y
C6 H6A O1 1_555 0.93 2.42 2.761(2) 102 y
C19 H19A Cg 1_655 0.93 2.82 3.641(2) 147 y
C21 H21A Cg 2_645 0.96 2.94 3.546(3) 122 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
C4 O1 C1 C2 . . . . 0.19(19) ?
O1 C1 C2 C3 . . . . 0.2(2) ?
C1 C2 C3 C4 . . . . -0.55(18) ?
C2 C3 C4 O1 . . . . 0.68(16) ?
C2 C3 C4 C5 . . . . -177.72(14) ?
C1 O1 C4 C3 . . . . -0.55(16) ?
C1 O1 C4 C5 . . . . 178.14(13) ?
C3 C4 C5 C6 . . . . 179.29(15) ?
O1 C4 C5 C6 . . . . 0.99(19) ?
C3 C4 C5 C10 . . . . 0.3(2) ?
O1 C4 C5 C10 . . . . -177.97(11) ?
C4 C5 C6 C7 . . . . -175.17(13) ?
C10 C5 C6 C7 . . . . 3.7(2) ?
C5 C6 C7 O2 . . . . -179.68(15) ?
C5 C6 C7 C8 . . . . 4.3(2) ?
O2 C7 C8 C11 . . . . 23.0(2) ?
C6 C7 C8 C11 . . . . -160.97(12) ?
O2 C7 C8 C9 . . . . 146.87(14) ?
C6 C7 C8 C9 . . . . -37.06(17) ?
C11 C8 C9 C14 . . . . -48.49(15) ?
C7 C8 C9 C14 . . . . -172.65(11) ?
C11 C8 C9 C10 . . . . -175.09(11) ?
C7 C8 C9 C10 . . . . 60.74(14) ?
C6 C5 C10 C9 . . . . 21.98(18) ?
C4 C5 C10 C9 . . . . -159.07(11) ?
C14 C9 C10 C5 . . . . -178.13(10) ?
C8 C9 C10 C5 . . . . -52.86(14) ?
C12 O4 C11 O3 . . . . 8.9(2) ?
C12 O4 C11 C8 . . . . -168.69(12) ?
C7 C8 C11 O3 . . . . 68.81(17) ?
C9 C8 C11 O3 . . . . -54.86(17) ?
C7 C8 C11 O4 . . . . -113.62(13) ?
C9 C8 C11 O4 . . . . 122.71(12) ?
C11 O4 C12 C13 . . . . 83.8(2) ?
C10 C9 C14 C19 . . . . 58.90(16) ?
C8 C9 C14 C19 . . . . -64.11(16) ?
C10 C9 C14 C15 . . . . -123.20(13) ?
C8 C9 C14 C15 . . . . 113.80(14) ?
C19 C14 C15 C16 . . . . 0.0(2) ?
C9 C14 C15 C16 . . . . -178.05(13) ?
C14 C15 C16 C17 . . . . -0.1(2) ?
C20 O5 C17 C16 . . . . 172.14(13) ?
C20 O5 C17 C18 . . . . -8.22(19) ?
C15 C16 C17 O5 . . . . 179.78(13) ?
C15 C16 C17 C18 . . . . 0.1(2) ?
O5 C17 C18 C19 . . . . -179.55(13) ?
C16 C17 C18 C19 . . . . 0.1(2) ?
C15 C14 C19 C18 . . . . 0.2(2) ?
C9 C14 C19 C18 . . . . 178.21(12) ?
C17 C18 C19 C14 . . . . -0.3(2) ?
C17 O5 C20 C21 . . . . -174.37(14) ?
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 3376113
