#------------------------------------------------------------------------------
#$Date: 2017-10-13 12:31:46 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201979 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/23/00/2230019.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_2230019
loop_
_publ_author_name
'Zukerman-Schpector, Julio'
'Abd Salim, Siti Nadiah'
'Moran, Paulo J. S.'
'de Paula, Bruno R. S.'
'Rodrigues, J. Augusto R.'
'Tiekink, Edward R. T.'
_publ_section_title
;
 Ethyl
 (2E)-2-(2H-1,3-benzodioxol-5-ylmethylidene)-4-chloro-3-oxobutanoate
;
_journal_coeditor_code           HG5017
_journal_issue                   5
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o1044
_journal_paper_doi               10.1107/S1600536811011780
_journal_volume                  67
_journal_year                    2011
_chemical_formula_iupac          'C14 H13 Cl O5'
_chemical_formula_moiety         'C14 H13 Cl O5'
_chemical_formula_sum            'C14 H13 Cl O5'
_chemical_formula_weight         296.69
_chemical_name_systematic
;
Ethyl
(2E)-2-(2H-1,3-benzodioxol-5-ylmethylidene)-4-chloro-3-
oxobutanoate
;
_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                   4.80420(10)
_cell_length_b                   14.9134(4)
_cell_length_c                   18.4793(5)
_cell_measurement_reflns_used    4024
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      28.55
_cell_measurement_theta_min      2.59
_cell_volume                     1323.99(6)
_computing_cell_refinement       'SAINT (Bruker, 2009)'
_computing_data_collection       'APEX2 (Bruker, 2009)'
_computing_data_reduction        'SAINT (Bruker, 2009)'
_computing_molecular_graphics
;
ORTEP-3 (Farrugia, 1997) and DIAMOND (Brandenburg, 2006)
;
_computing_publication_material
'MarvinSketch  (Chemaxon, 2010) and publCIF (Westrip, 2010)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_solution    'SIR97 (Altomare et al., 1999)'
_diffrn_ambient_temperature      100(2)
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_device_type  'Bruker SMART APEX diffractometer'
_diffrn_measurement_method       'ω scan'
_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  0.0405
_diffrn_reflns_av_sigmaI/netI    0.0341
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_k_max       19
_diffrn_reflns_limit_k_min       -19
_diffrn_reflns_limit_l_max       24
_diffrn_reflns_limit_l_min       -24
_diffrn_reflns_number            13030
_diffrn_reflns_theta_full        27.99
_diffrn_reflns_theta_max         27.99
_diffrn_reflns_theta_min         1.75
_diffrn_standards_decay_%        0
_diffrn_standards_interval_count 0
_diffrn_standards_interval_time  0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.305
_exptl_absorpt_correction_T_max  0.7461
_exptl_absorpt_correction_T_min  0.6360
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SADABS; Sheldrick, 1996)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.488
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       needle
_exptl_crystal_F_000             616
_exptl_crystal_size_max          0.28
_exptl_crystal_size_mid          0.07
_exptl_crystal_size_min          0.06
_refine_diff_density_max         0.282
_refine_diff_density_min         -0.183
_refine_ls_abs_structure_details
;
Flack (1983), 1312 Friedel pairs
;
_refine_ls_abs_structure_Flack   -0.03(5)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.053
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     182
_refine_ls_number_reflns         3200
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.053
_refine_ls_R_factor_all          0.0352
_refine_ls_R_factor_gt           0.0305
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_max_lt       0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0415P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0711
_refine_ls_wR_factor_ref         0.0734
_reflns_number_gt                2915
_reflns_number_total             3200
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            hg5017.cif
_cod_data_source_block           I
_cod_database_code               2230019
_cod_database_fobs_code          2230019
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'x+1/2, -y+1/2, -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
Cl Cl 0.61259(8) -0.13689(2) 0.67747(2) 0.02387(11) Uani d . 1 . .
O O1 0.3303(2) 0.08014(8) 1.03191(6) 0.0210(3) Uani d . 1 . .
O O2 0.1425(2) 0.01153(7) 0.93013(5) 0.0176(2) Uani d . 1 . .
O O3 0.3855(2) 0.04539(7) 0.66362(5) 0.0184(2) Uani d . 1 . .
O O4 0.8831(2) 0.13250(7) 0.57678(5) 0.0175(2) Uani d . 1 . .
O O5 1.0712(2) 0.23928(7) 0.64786(5) 0.0166(2) Uani d . 1 . .
C C1 0.1462(4) 0.00951(11) 1.00813(8) 0.0184(3) Uani d . 1 . .
H H1A 0.2128 -0.0482 1.0251 0.022 Uiso calc R 1 . .
H H1B -0.0397 0.0191 1.0271 0.022 Uiso calc R 1 . .
C C2 0.4641(3) 0.10950(10) 0.97104(8) 0.0146(3) Uani d . 1 . .
C C3 0.6715(3) 0.17232(10) 0.96631(8) 0.0167(3) Uani d . 1 . .
H H3 0.7441 0.2001 1.0072 0.020 Uiso calc R 1 . .
C C4 0.7684(3) 0.19244(10) 0.89674(8) 0.0154(3) Uani d . 1 . .
H H4 0.9067 0.2356 0.8914 0.018 Uiso calc R 1 . .
C C5 0.6645(3) 0.14994(9) 0.83495(8) 0.0132(3) Uani d . 1 . .
C C6 0.4459(3) 0.08662(10) 0.84196(8) 0.0148(3) Uani d . 1 . .
H H6 0.3688 0.0587 0.8017 0.018 Uiso calc R 1 . .
C C7 0.3532(3) 0.06826(9) 0.91020(8) 0.0140(3) Uani d . 1 . .
C C8 0.7904(3) 0.17377(10) 0.76594(8) 0.0144(3) Uani d . 1 . .
H H8 0.8986 0.2255 0.7666 0.017 Uiso calc R 1 . .
C C9 0.7744(3) 0.13267(10) 0.70152(8) 0.0136(3) Uani d . 1 . .
C C10 0.6222(3) 0.04657(10) 0.68599(7) 0.0135(3) Uani d . 1 . .
C C11 0.7940(3) -0.03659(10) 0.69812(9) 0.0177(3) Uani d . 1 . .
H H11A 0.8527 -0.0384 0.7483 0.021 Uiso calc R 1 . .
H H11B 0.9600 -0.0333 0.6684 0.021 Uiso calc R 1 . .
C C12 0.9143(3) 0.16725(10) 0.63571(8) 0.0136(3) Uani d . 1 . .
C C13 1.2296(4) 0.27097(11) 0.58593(9) 0.0214(4) Uani d . 1 . .
H H13A 1.1049 0.2886 0.5472 0.026 Uiso calc R 1 . .
H H13B 1.3509 0.2239 0.5681 0.026 Uiso calc R 1 . .
C C14 1.3985(4) 0.34985(11) 0.61063(9) 0.0251(4) Uani d . 1 . .
H H14A 1.2761 0.3969 0.6263 0.038 Uiso calc R 1 . .
H H14B 1.5112 0.3711 0.5713 0.038 Uiso calc R 1 . .
H H14C 1.5162 0.3321 0.6501 0.038 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'
Cl Cl 0.1484 0.1585 '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 O1 C1 . . 105.73(11) ?
C7 O2 C1 . . 105.82(12) ?
C12 O5 C13 . . 115.22(11) ?
O2 C1 O1 . . 107.25(12) ?
O2 C1 H1A . . 110.3 ?
O1 C1 H1A . . 110.3 ?
O2 C1 H1B . . 110.3 ?
O1 C1 H1B . . 110.3 ?
H1A C1 H1B . . 108.5 ?
O1 C2 C3 . . 127.81(14) ?
O1 C2 C7 . . 110.13(13) ?
C3 C2 C7 . . 122.03(14) ?
C2 C3 C4 . . 116.55(14) ?
C2 C3 H3 . . 121.7 ?
C4 C3 H3 . . 121.7 ?
C5 C4 C3 . . 122.29(14) ?
C5 C4 H4 . . 118.9 ?
C3 C4 H4 . . 118.9 ?
C4 C5 C6 . . 119.44(13) ?
C4 C5 C8 . . 117.17(14) ?
C6 C5 C8 . . 123.38(13) ?
C7 C6 C5 . . 117.36(13) ?
C7 C6 H6 . . 121.3 ?
C5 C6 H6 . . 121.3 ?
C6 C7 O2 . . 127.85(14) ?
C6 C7 C2 . . 122.28(14) ?
O2 C7 C2 . . 109.85(13) ?
C9 C8 C5 . . 129.98(14) ?
C9 C8 H8 . . 115.0 ?
C5 C8 H8 . . 115.0 ?
C8 C9 C12 . . 122.92(14) ?
C8 C9 C10 . . 125.93(14) ?
C12 C9 C10 . . 111.14(12) ?
O3 C10 C9 . . 122.29(14) ?
O3 C10 C11 . . 123.62(14) ?
C9 C10 C11 . . 114.05(12) ?
C10 C11 Cl . . 113.15(11) ?
C10 C11 H11A . . 108.9 ?
Cl C11 H11A . . 108.9 ?
C10 C11 H11B . . 108.9 ?
Cl C11 H11B . . 108.9 ?
H11A C11 H11B . . 107.8 ?
O4 C12 O5 . . 124.39(14) ?
O4 C12 C9 . . 122.08(14) ?
O5 C12 C9 . . 113.52(12) ?
O5 C13 C14 . . 107.37(13) ?
O5 C13 H13A . . 110.2 ?
C14 C13 H13A . . 110.2 ?
O5 C13 H13B . . 110.2 ?
C14 C13 H13B . . 110.2 ?
H13A C13 H13B . . 108.5 ?
C13 C14 H14A . . 109.5 ?
C13 C14 H14B . . 109.5 ?
H14A C14 H14B . . 109.5 ?
C13 C14 H14C . . 109.5 ?
H14A C14 H14C . . 109.5 ?
H14B C14 H14C . . 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
Cl C11 . 1.7728(15) ?
O1 C2 . 1.3674(18) ?
O1 C1 . 1.4440(19) ?
O2 C7 . 1.3698(18) ?
O2 C1 . 1.4417(18) ?
O3 C10 . 1.2100(19) ?
O4 C12 . 1.2153(18) ?
O5 C12 . 1.3316(18) ?
O5 C13 . 1.4533(18) ?
C1 H1A . 0.9700 ?
C1 H1B . 0.9700 ?
C2 C3 . 1.370(2) ?
C2 C7 . 1.388(2) ?
C3 C4 . 1.400(2) ?
C3 H3 . 0.9300 ?
C4 C5 . 1.398(2) ?
C4 H4 . 0.9300 ?
C5 C6 . 1.418(2) ?
C5 C8 . 1.456(2) ?
C6 C7 . 1.365(2) ?
C6 H6 . 0.9300 ?
C8 C9 . 1.341(2) ?
C8 H8 . 0.9300 ?
C9 C12 . 1.482(2) ?
C9 C10 . 1.505(2) ?
C10 C11 . 1.507(2) ?
C11 H11A . 0.9700 ?
C11 H11B . 0.9700 ?
C13 C14 . 1.500(2) ?
C13 H13A . 0.9700 ?
C13 H13B . 0.9700 ?
C14 H14A . 0.9600 ?
C14 H14B . 0.9600 ?
C14 H14C . 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
C1 H1a O4 2_655 0.97 2.50 3.348(2) 146
C11 H11b O3 1_655 0.97 2.36 3.1585(18) 139
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
C7 O2 C1 O1 . . . . 10.89(16) ?
C2 O1 C1 O2 . . . . -10.58(16) ?
C1 O1 C2 C3 . . . . -175.80(15) ?
C1 O1 C2 C7 . . . . 6.33(16) ?
O1 C2 C3 C4 . . . . -178.16(14) ?
C7 C2 C3 C4 . . . . -0.5(2) ?
C2 C3 C4 C5 . . . . -1.2(2) ?
C3 C4 C5 C6 . . . . 2.5(2) ?
C3 C4 C5 C8 . . . . -177.38(14) ?
C4 C5 C6 C7 . . . . -2.0(2) ?
C8 C5 C6 C7 . . . . 177.84(14) ?
C5 C6 C7 O2 . . . . 178.49(13) ?
C5 C6 C7 C2 . . . . 0.4(2) ?
C1 O2 C7 C6 . . . . 174.55(15) ?
C1 O2 C7 C2 . . . . -7.17(16) ?
O1 C2 C7 C6 . . . . 178.93(14) ?
C3 C2 C7 C6 . . . . 0.9(2) ?
O1 C2 C7 O2 . . . . 0.53(17) ?
C3 C2 C7 O2 . . . . -177.48(13) ?
C4 C5 C8 C9 . . . . 165.21(16) ?
C6 C5 C8 C9 . . . . -14.7(3) ?
C5 C8 C9 C12 . . . . 179.08(14) ?
C5 C8 C9 C10 . . . . -2.2(3) ?
C8 C9 C10 O3 . . . . 94.20(19) ?
C12 C9 C10 O3 . . . . -86.95(16) ?
C8 C9 C10 C11 . . . . -87.96(19) ?
C12 C9 C10 C11 . . . . 90.88(15) ?
O3 C10 C11 Cl . . . . -0.83(19) ?
C9 C10 C11 Cl . . . . -178.63(10) ?
C13 O5 C12 O4 . . . . -5.4(2) ?
C13 O5 C12 C9 . . . . 175.26(13) ?
C8 C9 C12 O4 . . . . -175.13(15) ?
C10 C9 C12 O4 . . . . 6.0(2) ?
C8 C9 C12 O5 . . . . 4.2(2) ?
C10 C9 C12 O5 . . . . -174.69(12) ?
C12 O5 C13 C14 . . . . -178.22(13) ?
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 30656641
