#------------------------------------------------------------------------------
#$Date: 2017-10-13 09:09:21 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201973 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/20/72/2207210.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_2207210
loop_
_publ_author_name
'Alpaslan, Gökhan'
'Özdamar, Özgür'
'Odabaşoğlu, Mustafa'
'Ersanlı, Cem Cüneyt'
'Erdönmez, Ahmet'
'Ocak Ískeleli, Nazan'
_publ_section_title
;
 (Z)-Ethyl
 4-chloro-2-[2-(2-chlorophenyl)hydrazono]-3-oxobutanoate
;
_journal_coeditor_code           DN6260
_journal_issue                   11
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o3648
_journal_page_last               o3650
_journal_paper_doi               10.1107/S1600536805032022
_journal_volume                  61
_journal_year                    2005
_chemical_formula_iupac          'C12 H12 Cl2 N2 O3'
_chemical_formula_moiety         'C12 H12 Cl2 N2 O3'
_chemical_formula_sum            'C12 H12 Cl2 N2 O3'
_chemical_formula_weight         303.14
_chemical_name_systematic
;
(Z)-Ethyl 4-chloro-2-[2-(2-chlorophenyl)hydrazono]-3-oxobutanoate
;
_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                95.000(5)
_cell_angle_beta                 94.336(5)
_cell_angle_gamma                102.054(5)
_cell_formula_units_Z            2
_cell_length_a                   4.466(5)
_cell_length_b                   9.248(5)
_cell_length_c                   17.078(5)
_cell_measurement_reflns_used    10737
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      27.1
_cell_measurement_theta_min      2.3
_cell_volume                     684.0(9)
_computing_cell_refinement       X-AREA
_computing_data_collection       'X-AREA (Stoe & Cie, 2002)'
_computing_data_reduction        'X-RED32 (Stoe & Cie, 2002)'
_computing_molecular_graphics
'ORTEPIII (Burnett & Johnson, 1996) and ORTEP-3 for Windows (Farrugia, 1997)'
_computing_publication_material  'WinGX (Farrugia, 1999)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 1997)'
_diffrn_ambient_temperature      296(2)
_diffrn_detector_area_resol_mean 6.67
_diffrn_measured_fraction_theta_full 1.00
_diffrn_measured_fraction_theta_max 1.00
_diffrn_measurement_device_type  'Stoe IPDS-II'
_diffrn_measurement_method       ω
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71069
_diffrn_reflns_av_R_equivalents  0.091
_diffrn_reflns_av_sigmaI/netI    0.070
_diffrn_reflns_limit_h_max       5
_diffrn_reflns_limit_h_min       -5
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_number            12555
_diffrn_reflns_theta_full        27.6
_diffrn_reflns_theta_max         27.2
_diffrn_reflns_theta_min         2.3
_diffrn_standards_decay_%        0.2
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.479
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.472
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             312
_exptl_crystal_size_max          0.48
_exptl_crystal_size_mid          0.21
_exptl_crystal_size_min          0.14
_refine_diff_density_max         0.18
_refine_diff_density_min         -0.22
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.907
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     173
_refine_ls_number_reflns         2986
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.907
_refine_ls_R_factor_all          0.1041
_refine_ls_R_factor_gt           0.0457
_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)+(0.059P)²] where P = (Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1052
_refine_ls_wR_factor_ref         0.1282
_reflns_number_gt                1545
_reflns_number_total             2986
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            dn6260.cif
_cod_data_source_block           I
_cod_database_code               2207210
_cod_database_fobs_code          2207210
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 0.9839(6) 0.7823(3) 0.77560(15) 0.0515(6) Uani d . 1 C
C2 1.1347(6) 0.8924(3) 0.73342(17) 0.0603(7) Uani d . 1 C
C3 1.3874(6) 0.9969(3) 0.76799(19) 0.0673(8) Uani d . 1 C
H3 1.4859 1.0703 0.7391 0.081 Uiso calc R 1 H
C4 1.4924(7) 0.9926(4) 0.8442(2) 0.0751(9) Uani d . 1 C
H4 1.6641 1.0624 0.8674 0.090 Uiso calc R 1 H
C5 1.3426(7) 0.8831(4) 0.88768(18) 0.0707(9) Uani d . 1 C
H5 1.4142 0.8806 0.9400 0.085 Uiso calc R 1 H
C6 1.0906(7) 0.7792(3) 0.85378(16) 0.0624(7) Uani d . 1 C
H6 0.9912 0.7068 0.8831 0.075 Uiso calc R 1 H
C7 0.3283(6) 0.4805(3) 0.74887(14) 0.0507(6) Uani d . 1 C
C8 0.2037(6) 0.4731(3) 0.66561(15) 0.0558(7) Uani d . 1 C
C9 -0.1599(7) 0.3485(4) 0.56098(16) 0.0684(8) Uani d . 1 C
H9A 0.0001 0.3462 0.5258 0.082 Uiso calc R 1 H
H9B -0.2525 0.4321 0.5514 0.082 Uiso calc R 1 H
C10 -0.3954(8) 0.2076(4) 0.5475(2) 0.0867(11) Uani d . 1 C
H10A -0.3000 0.1258 0.5564 0.130 Uiso calc R 1 H
H10B -0.4885 0.1949 0.4941 0.130 Uiso calc R 1 H
H10C -0.5503 0.2107 0.5833 0.130 Uiso calc R 1 H
C11 0.1857(6) 0.3839(3) 0.80598(15) 0.0563(7) Uani d . 1 C
C12 0.3633(7) 0.4045(4) 0.88698(16) 0.0716(9) Uani d . 1 C
H12A 0.4077 0.5090 0.9070 0.086 Uiso calc R 1 H
H12B 0.5578 0.3751 0.8822 0.086 Uiso calc R 1 H
N1 0.7262(5) 0.6773(2) 0.73902(13) 0.0563(6) Uani d . 1 N
H1 0.6685 0.6785 0.6899 0.068 Uiso calc R 1 H
N2 0.5752(5) 0.5785(2) 0.77951(12) 0.0529(6) Uani d . 1 N
O1 0.3132(5) 0.5626(2) 0.62157(11) 0.0729(6) Uani d . 1 O
O2 -0.0319(4) 0.3621(2) 0.64287(10) 0.0672(6) Uani d . 1 O
O3 -0.0582(5) 0.2969(3) 0.79184(11) 0.0814(7) Uani d . 1 O
Cl1 1.0007(2) 0.89767(10) 0.63575(5) 0.0843(3) Uani d . 1 Cl
Cl2 0.1590(2) 0.29945(11) 0.95506(4) 0.0862(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'
N N 0.0061 0.0033 '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
C2 C1 C6 118.8(2)
C2 C1 N1 119.8(2)
C6 C1 N1 121.4(2)
C3 C2 C1 120.9(3)
C3 C2 Cl1 120.0(2)
C1 C2 Cl1 119.1(2)
C4 C3 C2 120.0(3)
C4 C3 H3 120.0
C2 C3 H3 120.0
C3 C4 C5 119.9(3)
C3 C4 H4 120.0
C5 C4 H4 120.0
C6 C5 C4 120.4(3)
C6 C5 H5 119.8
C4 C5 H5 119.8
C5 C6 C1 119.9(3)
C5 C6 H6 120.0
C1 C6 H6 120.0
N2 C7 C11 113.4(2)
N2 C7 C8 122.5(2)
C11 C7 C8 124.1(2)
O1 C8 O2 122.9(2)
O1 C8 C7 122.4(2)
O2 C8 C7 114.8(2)
O2 C9 C10 106.7(2)
O2 C9 H9A 110.4
C10 C9 H9A 110.4
O2 C9 H9B 110.4
C10 C9 H9B 110.4
H9A C9 H9B 108.6
C9 C10 H10A 109.5
C9 C10 H10B 109.5
H10A C10 H10B 109.5
C9 C10 H10C 109.5
H10A C10 H10C 109.5
H10B C10 H10C 109.5
O3 C11 C7 123.8(2)
O3 C11 C12 121.1(3)
C7 C11 C12 115.1(2)
C11 C12 Cl2 112.4(2)
C11 C12 H12A 109.1
Cl2 C12 H12A 109.1
C11 C12 H12B 109.1
Cl2 C12 H12B 109.1
H12A C12 H12B 107.9
N2 N1 C1 119.9(2)
N2 N1 H1 120.0
C1 N1 H1 120.0
N1 N2 C7 122.5(2)
C8 O2 C9 116.9(2)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
C1 C2 1.387(4)
C1 C6 1.388(4)
C1 N1 1.405(3)
C2 C3 1.379(4)
C2 Cl1 1.737(3)
C3 C4 1.356(4)
C3 H3 0.9300
C4 C5 1.396(4)
C4 H4 0.9300
C5 C6 1.370(4)
C5 H5 0.9300
C6 H6 0.9300
C7 N2 1.313(3)
C7 C11 1.470(4)
C7 C8 1.478(3)
C8 O1 1.218(3)
C8 O2 1.315(3)
C9 O2 1.455(3)
C9 C10 1.482(4)
C9 H9A 0.9700
C9 H9B 0.9700
C10 H10A 0.9600
C10 H10B 0.9600
C10 H10C 0.9600
C11 O3 1.205(3)
C11 C12 1.518(3)
C12 Cl2 1.765(3)
C12 H12A 0.9700
C12 H12B 0.9700
N1 N2 1.301(3)
N1 H1 0.8600
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
N1 H1 O1 . 0.86 1.95 2.608(3) 132
C12 H12B O3 1_655 0.97 2.56 3.426(5) 148
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 21180149
