#------------------------------------------------------------------------------
#$Date: 2018-09-27 07:13:35 +0300 (Thu, 27 Sep 2018) $
#$Revision: 211196 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/20/69/2206922.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_2206922
loop_
_publ_author_name
'Alpaslan, Gökhan'
'Özdamar, Özgür'
'Odabaşoglu, Mustafa'
'Ersanlı, Cem Cüneyt'
'Erdönmez, Ahmet'
'Ocak Ískeleli, Nazan'
_publ_section_title
;
 (Z)-Ethyl
 4-chloro-2-[2-(2-methoxyphenyl)hydrazono]-3-oxobutanoate
;
_journal_issue                   10
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o3442
_journal_page_last               o3444
_journal_paper_doi               10.1107/S1600536805030163
_journal_volume                  61
_journal_year                    2005
_chemical_formula_iupac          'C13 H15 Cl N2 O4'
_chemical_formula_moiety         'C13 H15 Cl N2 O4'
_chemical_formula_sum            'C13 H15 Cl N2 O4'
_chemical_formula_weight         298.72
_chemical_name_systematic
;
(Z)-ethyl 4-chloro-2-(2-(2-methoxyphenyl)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                107.615(5)
_cell_angle_beta                 103.543(5)
_cell_angle_gamma                94.952(5)
_cell_formula_units_Z            2
_cell_length_a                   8.605(5)
_cell_length_b                   8.981(5)
_cell_length_c                   9.974(5)
_cell_measurement_reflns_used    8830
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      27.2
_cell_measurement_theta_min      2.4
_cell_volume                     703.9(7)
_computing_cell_refinement       X-AREA
_computing_data_collection       'X-AREA (Stoe & Cie, 2002)'
_computing_data_reduction        'X-RED32 (Stoe & Cie, 2002)'
_computing_molecular_graphics    'ORTEP-3 for Windows (Farrugia, 1997)'
_computing_publication_material  'WinGX (Farrugia, 1999)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 1990)'
_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       w
_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  0.027
_diffrn_reflns_av_sigmaI/netI    0.025
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            10993
_diffrn_reflns_theta_full        26.0
_diffrn_reflns_theta_max         26.0
_diffrn_reflns_theta_min         2.4
_diffrn_standards_decay_%        0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.286
_exptl_absorpt_correction_T_max  0.964
_exptl_absorpt_correction_T_min  0.885
_exptl_absorpt_correction_type   integration
_exptl_absorpt_process_details   '(X-RED32; Stoe & Cie, 2002)'
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.409
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       Prism
_exptl_crystal_F_000             312
_exptl_crystal_size_max          0.49
_exptl_crystal_size_mid          0.36
_exptl_crystal_size_min          0.14
_refine_diff_density_max         0.15
_refine_diff_density_min         -0.18
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.03
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     187
_refine_ls_number_reflns         2741
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.03
_refine_ls_R_factor_all          0.062
_refine_ls_R_factor_gt           0.040
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         <0.001
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0645P)²+0.0281P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.107
_refine_ls_wR_factor_ref         0.117
_reflns_number_gt                1906
_reflns_number_total             2741
_reflns_threshold_expression     'I >2σ(I)'
_cod_data_source_file            ci6657.cif
_cod_data_source_block           I
_cod_depositor_comments
;
The following automatic conversions were performed:
'_symmetry_cell_setting' value 'Triclinic' changed to 'triclinic'
according to '/home/saulius/struct/CIF-dictionaries/cif_core.dic'
dictionary named 'cif_core.dic' version 2.4.1 from 2010-06-29.

Automatic conversion script
Id: cif_fix_enum 1527 2010-12-29 10:47:43Z saulius 

The following automatic conversions were performed:

'_symmetry_cell_setting' value 'Triclinic' changed to 'triclinic'
according to /home/saulius/struct/CIF-dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.1 from 2010-06-29.

Automatic conversion script
Id: cif_fix_values 1715 2011-07-08 13:25:40Z adriana 
;
_cod_database_code               2206922
_cod_database_fobs_code          2206922
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 0.1950(2) 0.5853(2) 0.4889(2) 0.0594(5) Uani d . 1 C
C2 0.1743(3) 0.7305(3) 0.5723(2) 0.0744(6) Uani d . 1 C
H2 0.2404 0.7782 0.6673 0.089 Uiso calc R 1 H
C3 0.0556(3) 0.8064(3) 0.5156(3) 0.0921(7) Uani d . 1 C
H3 0.0405 0.9043 0.5725 0.110 Uiso calc R 1 H
C4 -0.0399(3) 0.7356(4) 0.3742(4) 0.0964(9) Uani d . 1 C
H4 -0.1204 0.7861 0.3361 0.116 Uiso calc R 1 H
C5 -0.0184(3) 0.5927(4) 0.2894(3) 0.0833(7) Uani d . 1 C
H5 -0.0828 0.5474 0.1935 0.100 Uiso calc R 1 H
C6 0.0993(2) 0.5143(3) 0.3454(2) 0.0655(5) Uani d . 1 C
C7 0.0222(3) 0.2850(4) 0.1324(2) 0.0999(8) Uani d . 1 C
H7A -0.0867 0.2728 0.1408 0.120 Uiso calc R 1 H
H7B 0.0507 0.1824 0.0953 0.120 Uiso calc R 1 H
H7C 0.0293 0.3426 0.0665 0.120 Uiso calc R 1 H
C8 0.4985(2) 0.4883(2) 0.74401(18) 0.0521(4) Uani d . 1 C
C9 0.5891(2) 0.5861(2) 0.89488(19) 0.0554(4) Uani d . 1 C
C10 0.5456(3) 0.7501(2) 0.9452(2) 0.0768(6) Uani d . 1 C
H10A 0.4391 0.7408 0.9618 0.092 Uiso calc R 1 H
H10B 0.5400 0.7961 0.8682 0.092 Uiso calc R 1 H
C11 0.5138(2) 0.3230(2) 0.67202(19) 0.0568(4) Uani d . 1 C
C12 0.6319(3) 0.1000(2) 0.6823(2) 0.0728(6) Uani d . 1 C
H12A 0.6634 0.0902 0.5931 0.087 Uiso calc R 1 H
H12B 0.5289 0.0308 0.6572 0.087 Uiso calc R 1 H
C13 0.7580(3) 0.0549(3) 0.7864(3) 0.0876(7) Uani d . 1 C
H13A 0.8588 0.1253 0.8119 0.105 Uiso calc R 1 H
H13B 0.7719 -0.0519 0.7413 0.105 Uiso calc R 1 H
H13C 0.7243 0.0623 0.8731 0.105 Uiso calc R 1 H
N1 0.30838(19) 0.5002(2) 0.54512(17) 0.0570(4) Uani d . 1 N
N2 0.39947(17) 0.56386(17) 0.67872(15) 0.0536(4) Uani d . 1 N
O1 0.43650(18) 0.24860(17) 0.54691(14) 0.0750(4) Uani d . 1 O
O2 0.61716(17) 0.26297(15) 0.75319(13) 0.0645(4) Uani d . 1 O
O3 0.68687(18) 0.54210(16) 0.97574(14) 0.0745(4) Uani d . 1 O
O4 0.13042(18) 0.3696(2) 0.27202(15) 0.0792(4) Uani d . 1 O
Cl1 0.68642(8) 0.87846(7) 1.10700(6) 0.0881(2) Uani d . 1 Cl
H1 0.307(3) 0.412(3) 0.499(3) 0.074(7) Uiso d . 1 H
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
_geom_angle_publ_flag
C2 C1 C6 120.45(19) ?
C2 C1 N1 121.94(18) ?
C6 C1 N1 117.6(2) ?
C1 C2 C3 120.2(2) ?
C1 C2 H2 119.9 ?
C3 C2 H2 119.9 ?
C4 C3 C2 119.4(3) ?
C4 C3 H3 120.3 ?
C2 C3 H3 120.3 ?
C5 C4 C3 120.9(2) ?
C5 C4 H4 119.5 ?
C3 C4 H4 119.5 ?
C4 C5 C6 120.3(2) ?
C4 C5 H5 119.8 ?
C6 C5 H5 119.8 ?
O4 C6 C5 125.7(2) ?
O4 C6 C1 115.59(18) ?
C5 C6 C1 118.7(2) ?
O4 C7 H7A 109.5 ?
O4 C7 H7B 109.5 ?
H7A C7 H7B 109.5 ?
O4 C7 H7C 109.5 ?
H7A C7 H7C 109.5 ?
H7B C7 H7C 109.5 ?
N2 C8 C11 122.51(15) ?
N2 C8 C9 112.68(16) y
C11 C8 C9 124.8(2) y
O3 C9 C8 124.6(2) y
O3 C9 C10 121.01(16) ?
C8 C9 C10 114.38(15) y
C9 C10 Cl1 112.93(14) ?
C9 C10 H10A 109.0 ?
Cl1 C10 H10A 109.0 ?
C9 C10 H10B 109.0 ?
Cl1 C10 H10B 109.0 ?
H10A C10 H10B 107.8 ?
O1 C11 O2 123.04(18) y
O1 C11 C8 121.8(2) ?
O2 C11 C8 115.15(15) y
O2 C12 C13 107.74(17) ?
O2 C12 H12A 110.2 ?
C13 C12 H12A 110.2 ?
O2 C12 H12B 110.2 ?
C13 C12 H12B 110.2 ?
H12A C12 H12B 108.5 ?
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 ?
N2 N1 C1 118.9(2) y
N2 N1 H1 121.6(18) ?
C1 N1 H1 119.1(18) ?
N1 N2 C8 122.97(16) y
C11 O2 C12 115.11(15) ?
C6 O4 C7 117.03(19) ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_publ_flag
C1 C2 1.370(3) ?
C1 C6 1.392(3) ?
C1 N1 1.408(2) ?
C2 C3 1.382(3) ?
C2 H2 0.93 ?
C3 C4 1.376(4) ?
C3 H3 0.93 ?
C4 C5 1.362(4) ?
C4 H4 0.93 ?
C5 C6 1.389(3) ?
C5 H5 0.93 ?
C6 O4 1.368(3) y
C7 O4 1.419(3) y
C7 H7A 0.96 ?
C7 H7B 0.96 ?
C7 H7C 0.96 ?
C8 N2 1.311(2) ?
C8 C11 1.473(3) ?
C8 C9 1.475(2) ?
C9 O3 1.203(2) y
C9 C10 1.516(3) ?
C10 Cl1 1.766(2) ?
C10 H10A 0.97 ?
C10 H10B 0.97 ?
C11 O1 1.215(2) y
C11 O2 1.321(2) y
C12 O2 1.451(2) y
C12 C13 1.491(3) ?
C12 H12A 0.97 ?
C12 H12B 0.97 ?
C13 H13A 0.96 ?
C13 H13B 0.96 ?
C13 H13C 0.96 ?
N1 N2 1.300(2) ?
N1 H1 0.79(2) ?
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
C5 H5 O3 1_454 0.93 2.56 3.413(3) 153
N1 H1 O1 . 0.79(2) 2.02(2) 2.602(2) 131(2)
N1 H1 O4 . 0.79(2) 2.31(2) 2.635(2) 106(2)
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
C6 C1 C2 C3 1.4(3) ?
N1 C1 C2 C3 -176.44(19) ?
C1 C2 C3 C4 -0.8(4) ?
C2 C3 C4 C5 -0.5(4) ?
C3 C4 C5 C6 1.1(4) ?
C4 C5 C6 O4 178.8(2) ?
C4 C5 C6 C1 -0.5(3) ?
C2 C1 C6 O4 179.86(18) ?
N1 C1 C6 O4 -2.2(2) y
C2 C1 C6 C5 -0.8(3) ?
N1 C1 C6 C5 177.21(18) ?
N2 C8 C9 O3 -179.88(17) ?
C11 C8 C9 O3 0.6(3) ?
N2 C8 C9 C10 2.1(2) ?
C11 C8 C9 C10 -177.41(18) ?
O3 C9 C10 Cl1 15.7(3) ?
C8 C9 C10 Cl1 -166.16(14) ?
N2 C8 C11 O1 1.0(3) ?
C9 C8 C11 O1 -179.55(18) ?
N2 C8 C11 O2 -179.07(16) ?
C9 C8 C11 O2 0.4(3) ?
C2 C1 N1 N2 -2.2(3) ?
C6 C1 N1 N2 179.89(16) ?
C1 N1 N2 C8 174.2(2) y
C11 C8 N2 N1 -0.8(3) ?
C9 C8 N2 N1 179.69(16) ?
O1 C11 O2 C12 -0.2(3) ?
C8 C11 O2 C12 179.9(2) ?
C13 C12 O2 C11 177.42(18) ?
C5 C6 O4 C7 -7.0(3) ?
C1 C6 O4 C7 172.30(19) ?
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 21180294
