#------------------------------------------------------------------------------
#$Date: 2017-10-13 12:31:46 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201979 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/23/04/2230441.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_2230441
loop_
_publ_author_name
'Wu, Liuming'
'Deng, Cong'
'Yang, Yan'
_publ_section_title
;
 (E)-Ethyl 2-benzoyl-4-(naphthalen-2-yl)-4-oxobut-2-enoate
;
_journal_coeditor_code           PK2318
_journal_issue                   6
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o1499
_journal_paper_doi               10.1107/S1600536811018745
_journal_volume                  67
_journal_year                    2011
_chemical_formula_iupac          'C23 H18 O4'
_chemical_formula_moiety         'C23 H18 O4'
_chemical_formula_sum            'C23 H18 O4'
_chemical_formula_weight         358.37
_chemical_name_systematic
;
(E)-Ethyl 2-benzoyl-4-(naphthalen-2-yl)-4-oxobut-2-enoate
;
_space_group_IT_number           2
_symmetry_cell_setting           triclinic
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                99.364(3)
_cell_angle_beta                 105.094(3)
_cell_angle_gamma                110.648(3)
_cell_formula_units_Z            2
_cell_length_a                   7.8571(13)
_cell_length_b                   9.6157(16)
_cell_length_c                   13.934(2)
_cell_measurement_reflns_used    2846
_cell_measurement_temperature    298(2)
_cell_measurement_theta_max      27.72
_cell_measurement_theta_min      2.36
_cell_volume                     912.6(3)
_computing_cell_refinement       'SAINT (Bruker, 2001)'
_computing_data_collection       'SMART (Bruker, 2001)'
_computing_data_reduction        'SAINT (Bruker, 2001)'
_computing_molecular_graphics    'PLATON (Spek, 2009)'
_computing_publication_material
'PLATON (Spek, 2009), SHELXL97 (Sheldrick, 2008) and publCIF (Westrip, 2010)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      298(2)
_diffrn_measured_fraction_theta_full 0.987
_diffrn_measured_fraction_theta_max 0.987
_diffrn_measurement_device_type  'Bruker SMART CCD area-detector'
_diffrn_measurement_method       'φ and 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  0.0649
_diffrn_reflns_av_sigmaI/netI    0.0567
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            5661
_diffrn_reflns_theta_full        25.50
_diffrn_reflns_theta_max         25.50
_diffrn_reflns_theta_min         2.36
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.089
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.304
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             376
_exptl_crystal_size_max          0.16
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.10
_refine_diff_density_max         0.177
_refine_diff_density_min         -0.187
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.051
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     245
_refine_ls_number_reflns         3355
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.051
_refine_ls_R_factor_all          0.0634
_refine_ls_R_factor_gt           0.0544
_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)+(0.0672P)²+0.1681P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1417
_refine_ls_wR_factor_ref         0.1488
_reflns_number_gt                2818
_reflns_number_total             3355
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            pk2318.cif
_cod_data_source_block           I
_cod_database_code               2230441
_cod_database_fobs_code          2230441
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -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
C C1 0.7525(2) 0.3380(2) 0.02603(13) 0.0480(4) Uani d . 1 1 . .
C C2 0.6361(3) 0.2384(2) -0.07533(14) 0.0594(5) Uani d . 1 1 . .
H H2 0.6065 0.1330 -0.0892 0.071 Uiso calc R 1 1 . .
C C3 0.5681(3) 0.2958(2) -0.15181(14) 0.0634(5) Uani d . 1 1 . .
H H3 0.4969 0.2295 -0.2183 0.076 Uiso calc R 1 1 . .
C C4 0.6024(3) 0.4539(2) -0.13326(13) 0.0526(4) Uani d . 1 1 . .
C C5 0.5236(3) 0.5168(3) -0.20967(15) 0.0644(5) Uani d . 1 1 . .
H H5 0.4507 0.4533 -0.2768 0.077 Uiso calc R 1 1 . .
C C6 0.5524(3) 0.6673(3) -0.18670(17) 0.0666(6) Uani d . 1 1 . .
H H6 0.4974 0.7056 -0.2377 0.080 Uiso calc R 1 1 . .
C C7 0.6642(3) 0.7654(3) -0.08709(17) 0.0673(6) Uani d . 1 1 . .
H H7 0.6839 0.8689 -0.0721 0.081 Uiso calc R 1 1 . .
C C8 0.7445(3) 0.7107(2) -0.01181(15) 0.0602(5) Uani d . 1 1 . .
H H8 0.8192 0.7776 0.0542 0.072 Uiso calc R 1 1 . .
C C9 0.7167(2) 0.5546(2) -0.03195(13) 0.0479(4) Uani d . 1 1 . .
C C10 0.7908(3) 0.4926(2) 0.04557(13) 0.0486(4) Uani d . 1 1 . .
H H10 0.8677 0.5582 0.1117 0.058 Uiso calc R 1 1 . .
C C11 0.8160(3) 0.2679(2) 0.10791(14) 0.0529(4) Uani d . 1 1 . .
C C12 0.9526(3) 0.3702(2) 0.21270(14) 0.0508(4) Uani d . 1 1 . .
H H12 1.0266 0.4736 0.2201 0.061 Uiso calc R 1 1 . .
C C13 0.9720(2) 0.31813(19) 0.29631(13) 0.0458(4) Uani d . 1 1 . .
C C14 0.8554(3) 0.1555(2) 0.29805(14) 0.0502(4) Uani d . 1 1 . .
C C15 0.9508(2) 0.04721(18) 0.29869(13) 0.0466(4) Uani d . 1 1 . .
C C16 0.9100(3) -0.0649(2) 0.35035(17) 0.0670(6) Uani d . 1 1 . .
H H16 0.8236 -0.0716 0.3859 0.080 Uiso calc R 1 1 . .
C C17 0.9978(4) -0.1679(3) 0.3492(2) 0.0811(7) Uani d . 1 1 . .
H H17 0.9701 -0.2430 0.3841 0.097 Uiso calc R 1 1 . .
C C18 1.1244(4) -0.1585(2) 0.29701(19) 0.0737(6) Uani d . 1 1 . .
H H18 1.1812 -0.2285 0.2954 0.088 Uiso calc R 1 1 . .
C C19 1.1676(3) -0.0474(3) 0.24748(18) 0.0707(6) Uani d . 1 1 . .
H H19 1.2550 -0.0409 0.2126 0.085 Uiso calc R 1 1 . .
C C20 1.0828(3) 0.0558(2) 0.24846(15) 0.0562(5) Uani d . 1 1 . .
H H20 1.1147 0.1322 0.2149 0.067 Uiso calc R 1 1 . .
C C21 1.1107(3) 0.4188(2) 0.40120(13) 0.0500(4) Uani d . 1 1 . .
C C22 1.3699(3) 0.6602(3) 0.49986(16) 0.0761(6) Uani d . 1 1 . .
H H22A 1.4252 0.6045 0.5412 0.091 Uiso calc R 1 1 . .
H H22B 1.3052 0.7056 0.5372 0.091 Uiso calc R 1 1 . .
C C23 1.5227(4) 0.7817(3) 0.4819(2) 0.0995(9) Uani d . 1 1 . .
H H23A 1.5909 0.7365 0.4485 0.149 Uiso calc R 1 1 . .
H H23B 1.6114 0.8551 0.5470 0.149 Uiso calc R 1 1 . .
H H23C 1.4664 0.8333 0.4386 0.149 Uiso calc R 1 1 . .
O O1 0.7583(2) 0.12815(15) 0.09194(11) 0.0762(5) Uani d . 1 1 . .
O O2 0.6987(2) 0.12270(17) 0.30777(13) 0.0743(4) Uani d . 1 1 . .
O O3 1.1113(3) 0.37690(18) 0.47767(11) 0.0809(5) Uani d . 1 1 . .
O O4 1.23194(19) 0.55455(14) 0.40043(9) 0.0607(4) Uani d . 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
C10 C1 C2 . . 118.91(16) ?
C10 C1 C11 . . 122.81(15) ?
C2 C1 C11 . . 118.14(16) ?
C3 C2 C1 . . 120.47(18) ?
C3 C2 H2 . . 119.8 ?
C1 C2 H2 . . 119.8 ?
C2 C3 C4 . . 121.70(17) ?
C2 C3 H3 . . 119.2 ?
C4 C3 H3 . . 119.2 ?
C3 C4 C5 . . 123.50(18) ?
C3 C4 C9 . . 118.46(17) ?
C5 C4 C9 . . 118.00(18) ?
C6 C5 C4 . . 121.28(19) ?
C6 C5 H5 . . 119.4 ?
C4 C5 H5 . . 119.4 ?
C5 C6 C7 . . 120.40(19) ?
C5 C6 H6 . . 119.8 ?
C7 C6 H6 . . 119.8 ?
C8 C7 C6 . . 120.4(2) ?
C8 C7 H7 . . 119.8 ?
C6 C7 H7 . . 119.8 ?
C7 C8 C9 . . 121.17(19) ?
C7 C8 H8 . . 119.4 ?
C9 C8 H8 . . 119.4 ?
C8 C9 C10 . . 122.55(16) ?
C8 C9 C4 . . 118.77(17) ?
C10 C9 C4 . . 118.61(16) ?
C1 C10 C9 . . 121.80(16) ?
C1 C10 H10 . . 119.1 ?
C9 C10 H10 . . 119.1 ?
O1 C11 C1 . . 121.54(17) ?
O1 C11 C12 . . 118.93(16) ?
C1 C11 C12 . . 119.53(15) ?
C13 C12 C11 . . 122.11(16) ?
C13 C12 H12 . . 118.9 ?
C11 C12 H12 . . 118.9 ?
C12 C13 C21 . . 122.55(16) ?
C12 C13 C14 . . 125.27(16) ?
C21 C13 C14 . . 112.15(14) ?
O2 C14 C15 . . 122.53(16) ?
O2 C14 C13 . . 120.11(16) ?
C15 C14 C13 . . 117.05(15) ?
C20 C15 C16 . . 118.37(18) ?
C20 C15 C14 . . 121.17(15) ?
C16 C15 C14 . . 120.46(17) ?
C15 C16 C17 . . 120.2(2) ?
C15 C16 H16 . . 119.9 ?
C17 C16 H16 . . 119.9 ?
C18 C17 C16 . . 120.1(2) ?
C18 C17 H17 . . 120.0 ?
C16 C17 H17 . . 120.0 ?
C19 C18 C17 . . 120.2(2) ?
C19 C18 H18 . . 119.9 ?
C17 C18 H18 . . 119.9 ?
C18 C19 C20 . . 120.4(2) ?
C18 C19 H19 . . 119.8 ?
C20 C19 H19 . . 119.8 ?
C19 C20 C15 . . 120.80(18) ?
C19 C20 H20 . . 119.6 ?
C15 C20 H20 . . 119.6 ?
O3 C21 O4 . . 124.25(17) ?
O3 C21 C13 . . 122.09(17) ?
O4 C21 C13 . . 113.65(15) ?
O4 C22 C23 . . 108.74(19) ?
O4 C22 H22A . . 109.9 ?
C23 C22 H22A . . 109.9 ?
O4 C22 H22B . . 109.9 ?
C23 C22 H22B . . 109.9 ?
H22A C22 H22B . . 108.3 ?
C22 C23 H23A . . 109.5 ?
C22 C23 H23B . . 109.5 ?
H23A C23 H23B . . 109.5 ?
C22 C23 H23C . . 109.5 ?
H23A C23 H23C . . 109.5 ?
H23B C23 H23C . . 109.5 ?
C21 O4 C22 . . 116.98(15) ?
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
C1 C10 . 1.373(2) ?
C1 C2 . 1.420(3) ?
C1 C11 . 1.482(2) ?
C2 C3 . 1.352(3) ?
C2 H2 . 0.9300 ?
C3 C4 . 1.413(3) ?
C3 H3 . 0.9300 ?
C4 C5 . 1.419(3) ?
C4 C9 . 1.421(3) ?
C5 C6 . 1.352(3) ?
C5 H5 . 0.9300 ?
C6 C7 . 1.394(3) ?
C6 H6 . 0.9300 ?
C7 C8 . 1.358(3) ?
C7 H7 . 0.9300 ?
C8 C9 . 1.406(3) ?
C8 H8 . 0.9300 ?
C9 C10 . 1.410(2) ?
C10 H10 . 0.9300 ?
C11 O1 . 1.217(2) ?
C11 C12 . 1.491(2) ?
C12 C13 . 1.335(2) ?
C12 H12 . 0.9300 ?
C13 C21 . 1.492(2) ?
C13 C14 . 1.517(2) ?
C14 O2 . 1.208(2) ?
C14 C15 . 1.482(3) ?
C15 C20 . 1.381(3) ?
C15 C16 . 1.383(3) ?
C16 C17 . 1.392(3) ?
C16 H16 . 0.9300 ?
C17 C18 . 1.365(4) ?
C17 H17 . 0.9300 ?
C18 C19 . 1.356(3) ?
C18 H18 . 0.9300 ?
C19 C20 . 1.377(3) ?
C19 H19 . 0.9300 ?
C20 H20 . 0.9300 ?
C21 O3 . 1.198(2) ?
C21 O4 . 1.321(2) ?
C22 O4 . 1.453(2) ?
C22 C23 . 1.459(3) ?
C22 H22A . 0.9700 ?
C22 H22B . 0.9700 ?
C23 H23A . 0.9600 ?
C23 H23B . 0.9600 ?
C23 H23C . 0.9600 ?
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
C10 C1 C2 C3 . . . . 1.5(3) ?
C11 C1 C2 C3 . . . . 177.41(18) ?
C1 C2 C3 C4 . . . . -2.8(3) ?
C2 C3 C4 C5 . . . . -175.90(18) ?
C2 C3 C4 C9 . . . . 2.0(3) ?
C3 C4 C5 C6 . . . . 176.54(19) ?
C9 C4 C5 C6 . . . . -1.4(3) ?
C4 C5 C6 C7 . . . . 1.2(3) ?
C5 C6 C7 C8 . . . . -0.4(3) ?
C6 C7 C8 C9 . . . . -0.3(3) ?
C7 C8 C9 C10 . . . . -177.10(18) ?
C7 C8 C9 C4 . . . . 0.1(3) ?
C3 C4 C9 C8 . . . . -177.29(18) ?
C5 C4 C9 C8 . . . . 0.7(3) ?
C3 C4 C9 C10 . . . . 0.0(2) ?
C5 C4 C9 C10 . . . . 178.01(16) ?
C2 C1 C10 C9 . . . . 0.4(3) ?
C11 C1 C10 C9 . . . . -175.22(16) ?
C8 C9 C10 C1 . . . . 176.00(17) ?
C4 C9 C10 C1 . . . . -1.2(3) ?
C10 C1 C11 O1 . . . . 169.80(19) ?
C2 C1 C11 O1 . . . . -5.9(3) ?
C10 C1 C11 C12 . . . . -9.7(3) ?
C2 C1 C11 C12 . . . . 174.56(16) ?
O1 C11 C12 C13 . . . . -19.2(3) ?
C1 C11 C12 C13 . . . . 160.31(17) ?
C11 C12 C13 C21 . . . . 178.92(16) ?
C11 C12 C13 C14 . . . . -3.1(3) ?
C12 C13 C14 O2 . . . . -84.9(2) ?
C21 C13 C14 O2 . . . . 93.3(2) ?
C12 C13 C14 C15 . . . . 101.4(2) ?
C21 C13 C14 C15 . . . . -80.41(19) ?
O2 C14 C15 C20 . . . . 153.77(19) ?
C13 C14 C15 C20 . . . . -32.7(2) ?
O2 C14 C15 C16 . . . . -26.5(3) ?
C13 C14 C15 C16 . . . . 147.00(18) ?
C20 C15 C16 C17 . . . . -1.3(3) ?
C14 C15 C16 C17 . . . . 178.96(18) ?
C15 C16 C17 C18 . . . . -0.1(3) ?
C16 C17 C18 C19 . . . . 1.1(4) ?
C17 C18 C19 C20 . . . . -0.7(3) ?
C18 C19 C20 C15 . . . . -0.8(3) ?
C16 C15 C20 C19 . . . . 1.7(3) ?
C14 C15 C20 C19 . . . . -178.54(18) ?
C12 C13 C21 O3 . . . . 170.97(19) ?
C14 C13 C21 O3 . . . . -7.2(2) ?
C12 C13 C21 O4 . . . . -10.2(2) ?
C14 C13 C21 O4 . . . . 171.62(15) ?
O3 C21 O4 C22 . . . . -2.0(3) ?
C13 C21 O4 C22 . . . . 179.16(16) ?
C23 C22 O4 C21 . . . . 164.2(2) ?
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 30656726
