##############################################################################
###                                                                        ###
###        Electronic paper (Acta Crystallographica Section E)             ###
###                                                                        ###
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#                                                                            #
# This CIF contains the data in a paper accepted for publication in Acta     #
# Crystallographica Section E. It conforms to the requirements of Notes      #
# for Authors for Section E, and has been peer reviewed under the auspices   #
# of the IUCr Commission on Journals.                                        #
#                                                                            #
# Full details of the Crystallographic Information File format               #
# are given in the paper "The Crystallographic Information File (CIF):       #
# a New Standard Archive File for Crystallography" by S. R. Hall, F. H.      #
# Allen and I. D. Brown [Acta Cryst. (1991), A47, 655-685].                  #
#                                                                            #
# The current version of the core CIF dictionary is obtainable from          #
# ftp://ftp.iucr.org/pub/cif_core.dic. The current version number is 2.4.    #
#                                                                            #
# Software is freely available for graphical display of the structure(s) in  #
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data_global
_audit_creation_method     SHELXL-97
_journal_date_recd_electronic     2010-08-11
_journal_date_accepted     2010-08-13
_journal_name_full     'Acta Crystallographica, Section E'
_journal_year     2010
_journal_volume     66
_journal_issue      9
_journal_page_first     o2374
_journal_page_last     o2374
_journal_paper_category     QO
_journal_coeditor_code     NK2054
_publ_contact_author
;
     Dr. Seik Weng Ng
     Department of Chemistry
     University of Malaya
     50603 Kuala Lumpur
     Malaysia
;
_publ_contact_author_email     seikweng@um.edu.my
_publ_contact_author_fax     '03 7967 4193'
_publ_contact_author_phone     '03 7967 6778'
_publ_section_title
;
Ethyl (Z)-2-chloro-2-(2-phenylhydrazin-1-ylidene)acetate
;
loop_
    _publ_author_name
    _publ_author_address
    'Asiri, Abdullah M.'
;
Chemistry Department
Faculty of Science
King Abdul Aziz University
PO Box 80203
Jeddah 21589
Saudi Arabia
;
    'Zayed, Mohie E. M.'
;
Chemistry Department
Faculty of Science
King Abdul Aziz University
PO Box 80203
Jeddah 21589
Saudi Arabia
;
    'Ng, Seik Weng'
;
Department of Chemistry
University of Malaya
50603 Kuala Lumpur
Malaysia
;
_publ_section_synopsis     .
data_I
_audit_creation_method     SHELXL-97
_chemical_name_systematic
;
Ethyl (Z)-2-chloro-2-(2-phenylhydrazin-1-ylidene)acetate
;
_chemical_name_common     ?
_chemical_formula_moiety     'C10 H11 Cl N2 O2'
_chemical_formula_sum     'C10 H11 Cl N2 O2'
_chemical_formula_iupac     'C10 H11 Cl N2 O2'
_chemical_formula_weight     226.66
_chemical_melting_point     ?
_symmetry_cell_setting     monoclinic
_symmetry_space_group_name_H-M     'P 21/c'
_symmetry_space_group_name_Hall     '-P 2ybc'
loop_
    _symmetry_equiv_pos_as_xyz
    'x, y, z'
    '-x, y+1/2, -z+1/2'
    '-x, -y, -z'
    'x, -y-1/2, z-1/2'
_cell_length_a     10.5091(7)
_cell_length_b     11.1813(8)
_cell_length_c     10.1190(7)
_cell_angle_alpha     90.00
_cell_angle_beta     118.1480(10)
_cell_angle_gamma     90.00
_cell_volume     1048.41(13)
_cell_formula_units_Z     4
_cell_measurement_reflns_used     4259
_cell_measurement_theta_min     2.3
_cell_measurement_theta_max     28.3
_cell_measurement_temperature     100(2)
_exptl_crystal_description     Irregular
_exptl_crystal_colour     Yellow
_exptl_crystal_size_max     0.30
_exptl_crystal_size_mid     0.30
_exptl_crystal_size_min     0.10
_exptl_crystal_density_diffrn     1.436
_exptl_crystal_density_meas     ?
_exptl_crystal_density_method     'not measured'
_exptl_crystal_F_000     472
_exptl_absorpt_coefficient_mu     0.345
_exptl_absorpt_correction_type     multi-scan
_exptl_absorpt_process_details     '(SADABS; Sheldrick, 1996)'
_exptl_absorpt_correction_T_min     0.9036
_exptl_absorpt_correction_T_max     0.9663
_diffrn_ambient_temperature     100(2)
_diffrn_radiation_type     MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_source     'fine-focus sealed tube'
_diffrn_radiation_monochromator     graphite
_diffrn_measurement_device_type     'Bruker SMART APEX diffractometer'
_diffrn_measurement_method     'ω scans'
_diffrn_detector_area_resol_mean     ?
_diffrn_reflns_number     6532
_diffrn_reflns_av_R_equivalents     0.0215
_diffrn_reflns_av_sigmaI/netI     0.0224
_diffrn_reflns_theta_min     2.20
_diffrn_reflns_theta_max     27.50
_diffrn_reflns_theta_full     27.50
_diffrn_measured_fraction_theta_max     0.999
_diffrn_measured_fraction_theta_full     0.999
_diffrn_reflns_limit_h_min     -13
_diffrn_reflns_limit_h_max     11
_diffrn_reflns_limit_k_min     -14
_diffrn_reflns_limit_k_max     12
_diffrn_reflns_limit_l_min     -13
_diffrn_reflns_limit_l_max     13
_diffrn_standards_number     0
_diffrn_standards_interval_count     0
_diffrn_standards_interval_time     0
_diffrn_standards_decay_%     0
_reflns_number_total     2399
_reflns_number_gt     2191
_reflns_threshold_expression     I>2σ(I)
_refine_ls_structure_factor_coef     Fsqd
_refine_ls_matrix_type     full
_refine_ls_R_factor_all     0.0290
_refine_ls_R_factor_gt     0.0264
_refine_ls_wR_factor_gt     0.0743
_refine_ls_wR_factor_ref     0.0764
_refine_ls_goodness_of_fit_ref     1.031
_refine_ls_restrained_S_all     1.031
_refine_ls_number_reflns     2399
_refine_ls_number_parameters     140
_refine_ls_number_restraints     1
_refine_ls_hydrogen_treatment     mixed
_refine_ls_weighting_scheme     calc
_refine_ls_weighting_details
         'calc w=1/[σ²(Fo²)+(0.0409P)²+0.3890P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_hydrogens     geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary     difmap
_refine_ls_shift/su_max     0.001
_refine_ls_shift/su_mean     0.001
_refine_diff_density_max     0.306
_refine_diff_density_min     -0.209
_refine_ls_extinction_method     none
_refine_ls_extinction_coef     ?
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'
_computing_data_collection     'APEX2 (Bruker, 2009)'
_computing_cell_refinement     'SAINT (Bruker, 2009)'
_computing_data_reduction     'SAINT (Bruker, 2009)'
_computing_structure_solution     'SHELXS97 (Sheldrick, 2008)'
_computing_structure_refinement     'SHELXL97 (Sheldrick, 2008)'
_computing_molecular_graphics     'X-SEED (Barbour, 2001)'
_computing_publication_material     'publCIF (Westrip, 2010)'
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 Cl1 0.52913(3) 0.54445(2) 0.33899(3) 0.02076(10) Uani d . 1 . .
    O O1 0.67383(8) 0.38123(7) 0.09626(9) 0.01737(18) Uani d . 1 . .
    O O2 0.49929(9) 0.33068(7) 0.15554(9) 0.01943(19) Uani d . 1 . .
    N N1 0.70432(10) 0.70808(8) 0.26261(10) 0.0153(2) Uani d D 1 . .
    H H1 0.6608(17) 0.7284(15) 0.3121(17) 0.032(4) Uiso d D 1 . .
    N N2 0.68722(10) 0.59913(8) 0.20434(10) 0.01443(19) Uani d . 1 . .
    C C1 0.78999(11) 0.79127(10) 0.23651(11) 0.0143(2) Uani d . 1 . .
    C C2 0.81229(12) 0.90363(10) 0.30391(12) 0.0171(2) Uani d . 1 . .
    H H2 0.7691 0.9232 0.3651 0.020 Uiso calc R 1 . .
    C C3 0.89810(12) 0.98666(11) 0.28081(13) 0.0201(2) Uani d . 1 . .
    H H3 0.9140 1.0629 0.3273 0.024 Uiso calc R 1 . .
    C C4 0.96101(13) 0.95973(11) 0.19073(14) 0.0208(2) Uani d . 1 . .
    H H4 1.0194 1.0170 0.1753 0.025 Uiso calc R 1 . .
    C C5 0.93736(12) 0.84780(11) 0.12342(13) 0.0201(2) Uani d . 1 . .
    H H5 0.9796 0.8289 0.0612 0.024 Uiso calc R 1 . .
    C C6 0.85275(12) 0.76310(10) 0.14599(12) 0.0167(2) Uani d . 1 . .
    H H6 0.8378 0.6866 0.1001 0.020 Uiso calc R 1 . .
    C C7 0.61141(12) 0.52090(10) 0.22737(12) 0.0152(2) Uani d . 1 . .
    C C8 0.58682(11) 0.40102(10) 0.15624(12) 0.0147(2) Uani d . 1 . .
    C C9 0.66715(12) 0.26082(10) 0.03770(13) 0.0176(2) Uani d . 1 . .
    H H9A 0.5698 0.2446 -0.0461 0.021 Uiso calc R 1 . .
    H H9B 0.6887 0.2006 0.1172 0.021 Uiso calc R 1 . .
    C C10 0.77830(12) 0.25572(12) -0.01594(13) 0.0213(3) Uani d . 1 . .
    H H10A 0.7777 0.1760 -0.0566 0.032 Uiso calc R 1 . .
    H H10B 0.8740 0.2719 0.0681 0.032 Uiso calc R 1 . .
    H H10C 0.7557 0.3159 -0.0943 0.032 Uiso calc R 1 . .
loop_
    _atom_site_aniso_label
    _atom_site_aniso_U_11
    _atom_site_aniso_U_22
    _atom_site_aniso_U_33
    _atom_site_aniso_U_12
    _atom_site_aniso_U_13
    _atom_site_aniso_U_23
    Cl1 0.02594(16) 0.01667(16) 0.02897(16) -0.00155(10) 0.02060(13)
                                                                    -0.00199(10)
    O1 0.0184(4) 0.0141(4) 0.0232(4) -0.0018(3) 0.0128(3) -0.0032(3)
    O2 0.0200(4) 0.0155(4) 0.0260(4) -0.0020(3) 0.0136(3) 0.0007(3)
    N1 0.0167(4) 0.0138(5) 0.0185(4) -0.0005(4) 0.0109(4) -0.0015(3)
    N2 0.0133(4) 0.0130(5) 0.0153(4) 0.0013(3) 0.0053(3) 0.0007(3)
    C1 0.0109(5) 0.0151(5) 0.0148(5) 0.0005(4) 0.0043(4) 0.0024(4)
    C2 0.0165(5) 0.0163(6) 0.0187(5) 0.0016(4) 0.0087(4) 0.0002(4)
    C3 0.0187(5) 0.0144(5) 0.0249(6) -0.0006(4) 0.0084(5) 0.0001(4)
    C4 0.0164(5) 0.0202(6) 0.0247(6) -0.0026(4) 0.0090(5) 0.0044(4)
    C5 0.0172(5) 0.0250(6) 0.0201(5) 0.0002(5) 0.0105(4) 0.0017(4)
    C6 0.0163(5) 0.0169(5) 0.0170(5) -0.0002(4) 0.0078(4) -0.0007(4)
    C7 0.0144(5) 0.0162(5) 0.0166(5) 0.0020(4) 0.0087(4) 0.0011(4)
    C8 0.0139(5) 0.0149(5) 0.0146(5) 0.0018(4) 0.0061(4) 0.0025(4)
    C9 0.0184(5) 0.0151(5) 0.0200(5) 0.0000(4) 0.0098(4) -0.0022(4)
    C10 0.0189(6) 0.0241(6) 0.0221(6) -0.0015(5) 0.0107(5) -0.0062(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
    Cl1 C7 . 1.7361(11) ?
    O1 C8 . 1.3331(13) ?
    O1 C9 . 1.4593(13) ?
    O2 C8 . 1.2076(14) ?
    N1 N2 . 1.3282(13) ?
    N1 C1 . 1.4035(14) ?
    N1 H1 . 0.853(13) ?
    N2 C7 . 1.2765(14) ?
    C1 C2 . 1.3957(16) ?
    C1 C6 . 1.3939(15) ?
    C2 C3 . 1.3888(16) ?
    C2 H2 . 0.9500 ?
    C3 C4 . 1.3883(17) ?
    C3 H3 . 0.9500 ?
    C4 C5 . 1.3900(17) ?
    C4 H4 . 0.9500 ?
    C5 C6 . 1.3897(16) ?
    C5 H5 . 0.9500 ?
    C6 H6 . 0.9500 ?
    C7 C8 . 1.4853(15) ?
    C9 C10 . 1.5035(15) ?
    C9 H9A . 0.9900 ?
    C9 H9B . 0.9900 ?
    C10 H10A . 0.9800 ?
    C10 H10B . 0.9800 ?
    C10 H10C . 0.9800 ?
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
    C8 O1 C9 . . 115.22(8) ?
    N2 N1 C1 . . 119.25(9) ?
    N2 N1 H1 . . 120.4(11) ?
    C1 N1 H1 . . 120.3(11) ?
    C7 N2 N1 . . 120.85(9) ?
    C2 C1 C6 . . 120.14(10) ?
    C2 C1 N1 . . 118.64(10) ?
    C6 C1 N1 . . 121.22(10) ?
    C3 C2 C1 . . 119.48(10) ?
    C3 C2 H2 . . 120.3 ?
    C1 C2 H2 . . 120.3 ?
    C4 C3 C2 . . 120.91(11) ?
    C4 C3 H3 . . 119.5 ?
    C2 C3 H3 . . 119.5 ?
    C5 C4 C3 . . 119.11(11) ?
    C5 C4 H4 . . 120.4 ?
    C3 C4 H4 . . 120.4 ?
    C4 C5 C6 . . 120.89(11) ?
    C4 C5 H5 . . 119.6 ?
    C6 C5 H5 . . 119.6 ?
    C5 C6 C1 . . 119.46(11) ?
    C5 C6 H6 . . 120.3 ?
    C1 C6 H6 . . 120.3 ?
    N2 C7 C8 . . 120.72(10) ?
    N2 C7 Cl1 . . 124.07(9) ?
    C8 C7 Cl1 . . 115.21(8) ?
    O2 C8 O1 . . 124.99(10) ?
    O2 C8 C7 . . 123.26(10) ?
    O1 C8 C7 . . 111.74(9) ?
    O1 C9 C10 . . 106.55(9) ?
    O1 C9 H9A . . 110.4 ?
    C10 C9 H9A . . 110.4 ?
    O1 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 ?
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
    C1 N1 N2 C7 . . . . 179.17(10) ?
    N2 N1 C1 C2 . . . . -177.17(9) ?
    N2 N1 C1 C6 . . . . 2.49(15) ?
    C6 C1 C2 C3 . . . . -0.40(16) ?
    N1 C1 C2 C3 . . . . 179.26(10) ?
    C1 C2 C3 C4 . . . . 0.50(17) ?
    C2 C3 C4 C5 . . . . -0.11(17) ?
    C3 C4 C5 C6 . . . . -0.38(17) ?
    C4 C5 C6 C1 . . . . 0.47(17) ?
    C2 C1 C6 C5 . . . . -0.08(16) ?
    N1 C1 C6 C5 . . . . -179.74(10) ?
    N1 N2 C7 C8 . . . . 177.11(9) ?
    N1 N2 C7 Cl1 . . . . -2.23(15) ?
    C9 O1 C8 O2 . . . . -5.24(15) ?
    C9 O1 C8 C7 . . . . 173.93(9) ?
    N2 C7 C8 O2 . . . . -168.44(10) ?
    Cl1 C7 C8 O2 . . . . 10.96(14) ?
    N2 C7 C8 O1 . . . . 12.38(14) ?
    Cl1 C7 C8 O1 . . . . -168.22(7) ?
    C8 O1 C9 C10 . . . . -176.85(9) ?
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
    _geom_hbond_publ_flag
    N1 H1 O2 2_655 0.850(10)
                           2.180(10)
                                   2.9690(10)
                                            153(2) yes
