#------------------------------------------------------------------------------
#$Date: 2017-10-13 09:09:21 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201973 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/20/31/2203120.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_2203120
loop_
_publ_author_name
'Wentrup, Curt'
'Buchanan, Jeff'
'Karl A. Byriel'
'Colin H.L. Kennard'
_publ_section_title
;
 Bis(2,4,6-trichlorophenyl) 2-ethylmalonate
;
_journal_issue                   1
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o137
_journal_page_last               o138
_journal_paper_doi               10.1107/S1600536803028812
_journal_volume                  60
_journal_year                    2004
_chemical_formula_iupac          'C17 H10 Cl6 O4'
_chemical_formula_moiety         'C17 H10 Cl6 O4'
_chemical_formula_sum            'C17 H10 Cl6 O4'
_chemical_formula_weight         490.95
_chemical_name_systematic
;
syn-Bis(2,4,6-trichlorophenyl) 2-ethylmalonate
;
_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           'WinGX-Routine XCAD4'
_cell_angle_alpha                91.41(2)
_cell_angle_beta                 92.98(2)
_cell_angle_gamma                112.26(2)
_cell_formula_units_Z            2
_cell_length_a                   7.648(3)
_cell_length_b                   8.532(2)
_cell_length_c                   16.947(6)
_cell_measurement_reflns_used    25
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      12.0
_cell_measurement_theta_min      10.0
_cell_volume                     1020.9(6)
_computing_cell_refinement       SDP
_computing_data_collection       'SDP (Frenz & Enraf-Nonius, 1985)'
_computing_data_reduction        'WinGX (Farrugia, 1999)'
_computing_molecular_graphics    'PLATON98 (Spek, 1998)'
_computing_publication_material  SHELXL97
_computing_structure_refinement  SHELXL97
_computing_structure_solution    'SHELXS97 (Sheldrick, 1997)'
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 0.938
_diffrn_measured_fraction_theta_max 0.938
_diffrn_measurement_device       'κ-geometry diffractometer'
_diffrn_measurement_device_type  'Enraf-Nonius CAD-4'
_diffrn_measurement_method       'non-profiled ω/2θ scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           Mok\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0078
_diffrn_reflns_av_sigmaI/netI    0.0231
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -1
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            3834
_diffrn_reflns_theta_full        25.00
_diffrn_reflns_theta_max         25.00
_diffrn_reflns_theta_min         2.41
_diffrn_standards_decay_%        0
_diffrn_standards_interval_time  60
_diffrn_standards_number         3
_exptl_absorpt_coefficient_mu    0.862
_exptl_absorpt_correction_T_max  0.8790
_exptl_absorpt_correction_T_min  0.8390
_exptl_absorpt_correction_type   '\y scan'
_exptl_absorpt_process_details   '(North et al., 1968)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.597
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             492
_exptl_crystal_size_max          0.20
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.15
_refine_diff_density_max         0.26
_refine_diff_density_min         -0.18
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.94
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     244
_refine_ls_number_reflns         3352
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.94
_refine_ls_R_factor_all          0.057
_refine_ls_R_factor_gt           0.034
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0572P)²+0.6749P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.088
_refine_ls_wR_factor_ref         0.103
_reflns_number_gt                2430
_reflns_number_total             3352
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            tk6145.cif
_cod_data_source_block           I
_cod_original_cell_volume        1020.8(6)
_cod_database_code               2203120
_cod_database_fobs_code          2203120
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'
loop_
_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_type_symbol
C1 -0.3001(4) -0.1455(3) 0.68878(13) 0.0433(6) Uani d . 1 C
O1 -0.1924(3) -0.1357(2) 0.62568(10) 0.0498(5) Uani d . 1 O
O11 -0.3881(3) -0.0589(3) 0.69682(11) 0.0620(5) Uani d . 1 O
C2 -0.2853(4) -0.2813(3) 0.74065(13) 0.0475(6) Uani d . 1 C
H2 -0.1514 -0.2650 0.7479 0.057 Uiso calc R 1 H
C21 -0.3933(6) -0.4569(4) 0.70219(17) 0.0713(9) Uani d . 1 C
H211 -0.5279 -0.4806 0.7009 0.086 Uiso calc R 1 H
H212 -0.3587 -0.4585 0.6480 0.086 Uiso calc R 1 H
C22 -0.3544(7) -0.5947(4) 0.7452(2) 0.0960(13) Uani d . 1 C
H221 -0.4241 -0.7024 0.7182 0.144 Uiso calc R 1 H
H222 -0.3930 -0.5968 0.7983 0.144 Uiso calc R 1 H
H223 -0.2215 -0.5724 0.7465 0.144 Uiso calc R 1 H
C3 -0.3538(4) -0.2595(3) 0.82098(14) 0.0467(6) Uani d . 1 C
O3 -0.2059(2) -0.1560(2) 0.86799(9) 0.0492(4) Uani d . 1 O
O31 -0.5111(3) -0.3227(3) 0.84130(12) 0.0703(6) Uani d . 1 O
C1A -0.1914(4) -0.0218(3) 0.56882(14) 0.0431(6) Uani d . 1 C
C2A -0.2997(4) -0.0785(3) 0.49804(14) 0.0444(6) Uani d . 1 C
Cl2A -0.45119(12) -0.28895(9) 0.48649(4) 0.0655(2) Uani d . 1 Cl
C3A -0.2877(4) 0.0281(3) 0.43697(14) 0.0476(6) Uani d . 1 C
H3A -0.3621 -0.0109 0.3900 0.057 Uiso calc R 1 H
C4A -0.1628(4) 0.1936(3) 0.44752(14) 0.0479(6) Uani d . 1 C
Cl4A -0.14205(13) 0.32926(9) 0.37086(4) 0.0683(2) Uani d . 1 Cl
C5A -0.0519(4) 0.2559(3) 0.51702(15) 0.0499(7) Uani d . 1 C
H5A 0.0319 0.3684 0.5228 0.060 Uiso calc R 1 H
C6A -0.0686(4) 0.1466(3) 0.57794(14) 0.0462(6) Uani d . 1 C
Cl6A 0.06730(12) 0.21929(10) 0.66528(4) 0.0666(2) Uani d . 1 Cl
C1B -0.2368(4) -0.1216(3) 0.94561(14) 0.0448(6) Uani d . 1 C
C2B -0.2435(4) 0.0334(3) 0.96610(15) 0.0475(6) Uani d . 1 C
Cl2B -0.23501(12) 0.17321(10) 0.89333(4) 0.0678(2) Uani d . 1 Cl
C3B -0.2534(4) 0.0783(4) 1.04424(15) 0.0527(7) Uani d . 1 C
H3B -0.2576 0.1829 1.0581 0.063 Uiso calc R 1 H
C4B -0.2569(4) -0.0354(4) 1.10089(15) 0.0532(7) Uani d . 1 C
Cl4B -0.26373(13) 0.02300(13) 1.19905(4) 0.0779(3) Uani d . 1 Cl
C5B -0.2527(4) -0.1914(4) 1.08224(15) 0.0538(7) Uani d . 1 C
H5B -0.2570 -0.2668 1.1215 0.065 Uiso calc R 1 H
C6B -0.2420(4) -0.2338(3) 1.00388(15) 0.0504(7) Uani d . 1 C
Cl6B -0.22947(13) -0.42623(10) 0.97877(5) 0.0726(3) Uani d . 1 Cl
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_
_diffrn_standard_refln_index_h
_diffrn_standard_refln_index_k
_diffrn_standard_refln_index_l
-1 -4 3
2 -2 -8
4 -3 -4
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_publ_flag
O11 C1 O1 122.6(2) ?
O11 C1 C2 129.1(2) y
O1 C1 C2 108.4(2) y
C1 O1 C1A 117.8(2) y
C1 C2 C3 108.8(2) y
C1 C2 C21 111.2(2) ?
C3 C2 C21 112.4(2) ?
C1 C2 H2 108.1 ?
C3 C2 H2 108.1 ?
C21 C2 H2 108.1 ?
C22 C21 C2 112.8(3) ?
C22 C21 H211 109.0 ?
C2 C21 H211 109.0 ?
C22 C21 H212 109.0 ?
C2 C21 H212 109.0 ?
H211 C21 H212 107.8 ?
C21 C22 H221 109.5 ?
C21 C22 H222 109.5 ?
H221 C22 H222 109.5 ?
C21 C22 H223 109.5 ?
H221 C22 H223 109.5 ?
H222 C22 H223 109.5 ?
O31 C3 O3 124.1(2) ?
O31 C3 C2 127.1(3) y
O3 C3 C2 108.9(2) y
C3 O3 C1B 118.4(2) y
O1 C1A C6A 120.8(2) ?
O1 C1A C2A 120.1(2) ?
C6A C1A C2A 118.8(2) ?
C3A C2A C1A 121.6(2) ?
C3A C2A Cl2A 119.6(2) ?
C1A C2A Cl2A 118.71(19) ?
C4A C3A C2A 118.1(2) ?
C4A C3A H3A 121.0 ?
C2A C3A H3A 121.0 ?
C3A C4A C5A 122.3(2) ?
C3A C4A Cl4A 118.9(2) ?
C5A C4A Cl4A 118.7(2) ?
C4A C5A C6A 118.4(2) ?
C4A C5A H5A 120.8 ?
C6A C5A H5A 120.8 ?
C1A C6A C5A 120.7(2) ?
C1A C6A Cl6A 119.48(19) ?
C5A C6A Cl6A 119.8(2) ?
C2B C1B C6B 119.5(2) ?
C2B C1B O3 119.4(2) ?
C6B C1B O3 120.8(2) ?
C1B C2B C3B 120.7(2) ?
C1B C2B Cl2B 119.26(19) ?
C3B C2B Cl2B 120.0(2) ?
C4B C3B C2B 118.5(3) ?
C4B C3B H3B 120.8 ?
C2B C3B H3B 120.8 ?
C5B C4B C3B 122.2(2) ?
C5B C4B Cl4B 119.4(2) ?
C3B C4B Cl4B 118.4(2) ?
C4B C5B C6B 118.5(3) ?
C4B C5B H5B 120.7 ?
C6B C5B H5B 120.7 ?
C5B C6B C1B 120.6(3) ?
C5B C6B Cl6B 119.7(2) ?
C1B C6B Cl6B 119.7(2) ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_publ_flag
C1 O11 1.183(3) ?
C1 O1 1.369(3) y
C1 C2 1.506(4) ?
O1 C1A 1.384(3) y
C2 C3 1.516(4) y
C2 C21 1.520(4) ?
C2 H2 0.9800 ?
C21 C22 1.512(5) ?
C21 H211 0.9700 ?
C21 H212 0.9700 ?
C22 H221 0.9600 ?
C22 H222 0.9600 ?
C22 H223 0.9600 ?
C3 O31 1.190(3) y
C3 O3 1.345(3) y
O3 C1B 1.392(3) y
C1A C6A 1.386(4) ?
C1A C2A 1.387(4) ?
C2A C3A 1.378(3) ?
C2A Cl2A 1.728(3) ?
C3A C4A 1.374(4) ?
C3A H3A 0.9300 ?
C4A C5A 1.383(4) ?
C4A Cl4A 1.735(2) ?
C5A C6A 1.386(3) ?
C5A H5A 0.9300 ?
C6A Cl6A 1.721(3) ?
C1B C2B 1.380(4) ?
C1B C6B 1.384(4) ?
C2B C3B 1.383(4) ?
C2B Cl2B 1.723(3) ?
C3B C4B 1.375(4) ?
C3B H3B 0.9300 ?
C4B C5B 1.373(4) ?
C4B Cl4B 1.734(3) ?
C5B C6B 1.382(4) ?
C5B H5B 0.9300 ?
C6B Cl6B 1.725(3) ?
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
_geom_torsion_publ_flag
C2A C1A O1 C1 -101.4(3) y
C1A O1 C1 C2 177.8(2) y
O1 C1 C2 C3 163.6(2) y
C1 C2 C3 O3 -90.0(3) y
C2 C3 O3 C1B -178.6(2) y
C3 O3 C1B C2B -104.3(3) y
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 2064467
