#------------------------------------------------------------------------------
#$Date: 2017-10-13 12:31:46 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201979 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/23/07/2230768.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_2230768
loop_
_publ_author_name
'Ismiyev, Arif I.'
_publ_section_title
;
 (Z)-Ethyl 2-benzylidene-3-oxobutanoate
;
_journal_coeditor_code           KP2335
_journal_issue                   7
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o1863
_journal_paper_doi               10.1107/S1600536811024974
_journal_volume                  67
_journal_year                    2011
_chemical_formula_iupac          'C13 H14 O3'
_chemical_formula_moiety         'C13 H14 O3'
_chemical_formula_sum            'C13 H14 O3'
_chemical_formula_weight         218.24
_chemical_name_systematic
;
(Z)-Ethyl 2-benzylidene-3-oxobutanoate
;
_space_group_IT_number           61
_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_Hall  '-P 2ac 2ab'
_symmetry_space_group_name_H-M   'P b c a'
_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                 90.00
_cell_angle_gamma                90.00
_cell_formula_units_Z            8
_cell_length_a                   7.8406(5)
_cell_length_b                   16.8767(12)
_cell_length_c                   17.5420(13)
_cell_measurement_reflns_used    1409
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      21.39
_cell_measurement_theta_min      2.32
_cell_volume                     2321.2(3)
_computing_cell_refinement       'SAINT-Plus (Bruker, 2001)'
_computing_data_collection       'APEX2 (Bruker, 2005)'
_computing_data_reduction        'SAINT-Plus (Bruker, 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      296(2)
_diffrn_measured_fraction_theta_full 0.994
_diffrn_measured_fraction_theta_max 0.994
_diffrn_measurement_device_type  'Bruker APEXII CCD'
_diffrn_measurement_method       'phi and omega 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  0.0734
_diffrn_reflns_av_sigmaI/netI    0.0420
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       21
_diffrn_reflns_limit_k_min       -21
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_number            17709
_diffrn_reflns_theta_full        27.00
_diffrn_reflns_theta_max         27.00
_diffrn_reflns_theta_min         2.32
_exptl_absorpt_coefficient_mu    0.088
_exptl_absorpt_correction_T_max  0.9982
_exptl_absorpt_correction_T_min  0.9974
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SADABS; Sheldrick, 1998)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.249
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             928
_exptl_crystal_size_max          0.03
_exptl_crystal_size_mid          0.03
_exptl_crystal_size_min          0.02
_refine_diff_density_max         0.181
_refine_diff_density_min         -0.165
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.995
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     147
_refine_ls_number_reflns         2515
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.995
_refine_ls_R_factor_all          0.1065
_refine_ls_R_factor_gt           0.0526
_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)+(0.0409P)²+0.8814P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1008
_refine_ls_wR_factor_ref         0.1248
_reflns_number_gt                1459
_reflns_number_total             2515
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            kp2335.cif
_cod_data_source_block           I
_cod_database_code               2230768
_cod_database_fobs_code          2230768
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'
'-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_symmetry_multiplicity
_atom_site_disorder_assembly
_atom_site_disorder_group
O O1 0.3871(2) 0.22540(10) 0.50159(10) 0.0679(5) Uani d . 1 1 . .
O O2 0.4542(2) 0.17527(10) 0.66960(9) 0.0577(5) Uani d . 1 1 . .
O O3 0.66163(18) 0.11601(9) 0.60314(8) 0.0488(4) Uani d . 1 1 . .
C C1 0.3604(3) -0.03682(12) 0.61668(12) 0.0416(5) Uani d . 1 1 . .
C C2 0.4421(3) -0.02544(14) 0.68650(12) 0.0511(6) Uani d . 1 1 . .
H H2A 0.4778 0.0251 0.7004 0.061 Uiso calc R 1 1 . .
C C3 0.4706(3) -0.08813(15) 0.73500(14) 0.0599(7) Uani d . 1 1 . .
H H3A 0.5266 -0.0798 0.7810 0.072 Uiso calc R 1 1 . .
C C4 0.4170(3) -0.16243(15) 0.71591(15) 0.0620(7) Uani d . 1 1 . .
H H4A 0.4371 -0.2047 0.7488 0.074 Uiso calc R 1 1 . .
C C5 0.3338(3) -0.17479(15) 0.64858(16) 0.0634(7) Uani d . 1 1 . .
H H5A 0.2960 -0.2254 0.6360 0.076 Uiso calc R 1 1 . .
C C6 0.3056(3) -0.11284(14) 0.59944(14) 0.0510(6) Uani d . 1 1 . .
H H6A 0.2488 -0.1220 0.5538 0.061 Uiso calc R 1 1 . .
C C7 0.3282(3) 0.02582(13) 0.56098(12) 0.0417(5) Uani d . 1 1 . .
H H7A 0.2576 0.0111 0.5208 0.050 Uiso calc R 1 1 . .
C C8 0.3835(3) 0.10083(13) 0.55822(11) 0.0403(5) Uani d . 1 1 . .
C C9 0.5003(3) 0.13555(12) 0.61673(12) 0.0410(5) Uani d . 1 1 . .
C C10 0.7862(3) 0.14424(16) 0.65832(14) 0.0585(7) Uani d . 1 1 . .
H H10A 0.7593 0.1242 0.7087 0.070 Uiso calc R 1 1 . .
H H10B 0.7859 0.2017 0.6601 0.070 Uiso calc R 1 1 . .
C C11 0.9541(3) 0.11498(19) 0.63350(16) 0.0738(8) Uani d . 1 1 . .
H H11A 1.0395 0.1312 0.6695 0.111 Uiso calc R 1 1 . .
H H11B 0.9807 0.1365 0.5842 0.111 Uiso calc R 1 1 . .
H H11C 0.9518 0.0582 0.6306 0.111 Uiso calc R 1 1 . .
C C12 0.3325(3) 0.15853(15) 0.49856(13) 0.0485(6) Uani d . 1 1 . .
C C13 0.2141(3) 0.13393(17) 0.43558(14) 0.0677(8) Uani d . 1 1 . .
H H13A 0.1707 0.1802 0.4103 0.102 Uiso calc R 1 1 . .
H H13B 0.1209 0.1041 0.4565 0.102 Uiso calc R 1 1 . .
H H13C 0.2749 0.1017 0.3996 0.102 Uiso calc R 1 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
C9 O3 C10 . . 116.00(17) ?
C6 C1 C2 . . 117.5(2) ?
C6 C1 C7 . . 118.0(2) ?
C2 C1 C7 . . 124.5(2) ?
C3 C2 C1 . . 120.8(2) ?
C3 C2 H2A . . 119.6 ?
C1 C2 H2A . . 119.6 ?
C4 C3 C2 . . 120.3(2) ?
C4 C3 H3A . . 119.8 ?
C2 C3 H3A . . 119.8 ?
C3 C4 C5 . . 120.0(2) ?
C3 C4 H4A . . 120.0 ?
C5 C4 H4A . . 120.0 ?
C4 C5 C6 . . 120.2(2) ?
C4 C5 H5A . . 119.9 ?
C6 C5 H5A . . 119.9 ?
C5 C6 C1 . . 121.2(2) ?
C5 C6 H6A . . 119.4 ?
C1 C6 H6A . . 119.4 ?
C8 C7 C1 . . 130.7(2) ?
C8 C7 H7A . . 114.6 ?
C1 C7 H7A . . 114.6 ?
C7 C8 C12 . . 124.0(2) ?
C7 C8 C9 . . 122.95(19) ?
C12 C8 C9 . . 113.07(19) ?
O2 C9 O3 . . 124.3(2) ?
O2 C9 C8 . . 124.4(2) ?
O3 C9 C8 . . 111.27(18) ?
O3 C10 C11 . . 107.1(2) ?
O3 C10 H10A . . 110.3 ?
C11 C10 H10A . . 110.3 ?
O3 C10 H10B . . 110.3 ?
C11 C10 H10B . . 110.3 ?
H10A C10 H10B . . 108.6 ?
C10 C11 H11A . . 109.5 ?
C10 C11 H11B . . 109.5 ?
H11A C11 H11B . . 109.5 ?
C10 C11 H11C . . 109.5 ?
H11A C11 H11C . . 109.5 ?
H11B C11 H11C . . 109.5 ?
O1 C12 C8 . . 119.1(2) ?
O1 C12 C13 . . 120.7(2) ?
C8 C12 C13 . . 120.3(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 ?
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 C12 . 1.208(3) ?
O2 C9 . 1.200(2) ?
O3 C9 . 1.329(2) ?
O3 C10 . 1.455(3) ?
C1 C6 . 1.386(3) ?
C1 C2 . 1.395(3) ?
C1 C7 . 1.462(3) ?
C2 C3 . 1.376(3) ?
C2 H2A . 0.9300 ?
C3 C4 . 1.364(4) ?
C3 H3A . 0.9300 ?
C4 C5 . 1.365(4) ?
C4 H4A . 0.9300 ?
C5 C6 . 1.373(3) ?
C5 H5A . 0.9300 ?
C6 H6A . 0.9300 ?
C7 C8 . 1.339(3) ?
C7 H7A . 0.9300 ?
C8 C12 . 1.484(3) ?
C8 C9 . 1.495(3) ?
C10 C11 . 1.472(3) ?
C10 H10A . 0.9700 ?
C10 H10B . 0.9700 ?
C11 H11A . 0.9600 ?
C11 H11B . 0.9600 ?
C11 H11C . 0.9600 ?
C12 C13 . 1.502(3) ?
C13 H13A . 0.9600 ?
C13 H13B . 0.9600 ?
C13 H13C . 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
C4 H4A O2 3.646 0.93 2.62 3.544(3) 170 yes
C5 H5A O2 8.655 0.93 2.648 3.412(3) 140 yes
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
C6 C1 C2 C3 . . . . 1.7(3) ?
C7 C1 C2 C3 . . . . -178.6(2) ?
C1 C2 C3 C4 . . . . -0.9(4) ?
C2 C3 C4 C5 . . . . -0.4(4) ?
C3 C4 C5 C6 . . . . 0.8(4) ?
C4 C5 C6 C1 . . . . 0.0(4) ?
C2 C1 C6 C5 . . . . -1.2(3) ?
C7 C1 C6 C5 . . . . 179.0(2) ?
C6 C1 C7 C8 . . . . -171.0(2) ?
C2 C1 C7 C8 . . . . 9.3(4) ?
C1 C7 C8 C12 . . . . -177.4(2) ?
C1 C7 C8 C9 . . . . 1.0(4) ?
C10 O3 C9 O2 . . . . 1.5(3) ?
C10 O3 C9 C8 . . . . -177.80(18) ?
C7 C8 C9 O2 . . . . -97.9(3) ?
C12 C8 C9 O2 . . . . 80.6(3) ?
C7 C8 C9 O3 . . . . 81.4(2) ?
C12 C8 C9 O3 . . . . -100.1(2) ?
C9 O3 C10 C11 . . . . 178.9(2) ?
C7 C8 C12 O1 . . . . 178.8(2) ?
C9 C8 C12 O1 . . . . 0.3(3) ?
C7 C8 C12 C13 . . . . -0.9(3) ?
C9 C8 C12 C13 . . . . -179.4(2) ?
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 4512450
