#------------------------------------------------------------------------------
#$Date: 2017-10-13 12:31:46 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201979 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/23/54/2235492.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_2235492
loop_
_publ_author_name
'Abdel-Aziz, Hatem A.'
'Chia, Tze Shyang'
'Fun, Hoong-Kun'
_publ_section_title
;
 1-Chloro-1-[(Z)-2-phenylhydrazin-1-ylidene]propan-2-one
;
_journal_coeditor_code           HB6870
_journal_issue                   7
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o2263
_journal_paper_doi               10.1107/S1600536812028759
_journal_volume                  68
_journal_year                    2012
_chemical_formula_moiety         'C9 H9 Cl N2 O'
_chemical_formula_sum            'C9 H9 Cl N2 O'
_chemical_formula_weight         196.63
_chemical_name_systematic
;
1-Chloro-1-[(Z)-2-phenylhydrazin-1-ylidene]propan-2-one
;
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 1 21/c 1'
_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                 101.158(3)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   7.2681(14)
_cell_length_b                   12.361(2)
_cell_length_c                   10.704(2)
_cell_measurement_reflns_used    3613
_cell_measurement_temperature    100.0(10)
_cell_measurement_theta_max      29.95
_cell_measurement_theta_min      2.54
_cell_volume                     943.5(3)
_computing_cell_refinement       'SAINT (Bruker, 2009)'
_computing_data_collection       'APEX2 (Bruker, 2009)'
_computing_data_reduction        'SAINT (Bruker, 2009)'
_computing_molecular_graphics    'SHELXTL (Sheldrick, 2008)'
_computing_publication_material
;
SHELXTL (Sheldrick, 2008) and PLATON (Spek, 2009)
;
_computing_structure_refinement  'SHELXTL (Sheldrick, 2008)'
_computing_structure_solution    'SHELXTL (Sheldrick, 2008)'
_diffrn_ambient_temperature      100.0(10)
_diffrn_measured_fraction_theta_full 0.991
_diffrn_measured_fraction_theta_max 0.991
_diffrn_measurement_device_type  'Bruker APEX DUO CCD'
_diffrn_measurement_method       'φ and ω scans'
_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  0.0300
_diffrn_reflns_av_sigmaI/netI    0.0345
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            8906
_diffrn_reflns_theta_full        29.98
_diffrn_reflns_theta_max         29.98
_diffrn_reflns_theta_min         2.86
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.364
_exptl_absorpt_correction_T_max  0.9631
_exptl_absorpt_correction_T_min  0.8771
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SADABS; Bruker, 2009)'
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.384
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             408
_exptl_crystal_size_max          0.37
_exptl_crystal_size_mid          0.21
_exptl_crystal_size_min          0.10
_refine_diff_density_max         0.860
_refine_diff_density_min         -0.369
_refine_ls_extinction_coef       0.008(3)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     'SHELXTL (Sheldrick, 2008)'
_refine_ls_goodness_of_fit_ref   1.060
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     124
_refine_ls_number_reflns         2722
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.060
_refine_ls_R_factor_all          0.0626
_refine_ls_R_factor_gt           0.0487
_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)+(0.0802P)²+0.7657P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1372
_refine_ls_wR_factor_ref         0.1478
_reflns_number_gt                2225
_reflns_number_total             2722
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            hb6870.cif
_cod_data_source_block           I
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               2235492
_cod_database_fobs_code          2235492
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'
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_symmetry_multiplicity
Cl Cl1 -0.00357(7) 0.01567(4) 0.18248(4) 0.02310(16) Uani d . 1 1
O O1 0.0096(2) 0.24567(12) 0.25220(13) 0.0275(3) Uani d . 1 1
N N1 0.1947(2) -0.08946(14) 0.41978(16) 0.0235(4) Uani d . 1 1
N N2 0.1820(2) 0.01726(13) 0.42826(16) 0.0220(3) Uani d . 1 1
C C1 0.2872(3) -0.26204(17) 0.51547(19) 0.0230(4) Uani d . 1 1
H H1A 0.2243 -0.2962 0.4397 0.028 Uiso calc R 1 1
C C2 0.3780(3) -0.32397(18) 0.6175(2) 0.0265(4) Uani d . 1 1
H H2A 0.3769 -0.4006 0.6112 0.032 Uiso calc R 1 1
C C3 0.4705(3) -0.27448(19) 0.72882(19) 0.0278(4) Uani d . 1 1
H H3A 0.5321 -0.3169 0.7985 0.033 Uiso calc R 1 1
C C4 0.4715(3) -0.16205(19) 0.7370(2) 0.0277(4) Uani d . 1 1
H H4A 0.5349 -0.1281 0.8128 0.033 Uiso calc R 1 1
C C5 0.3816(3) -0.09862(18) 0.63614(19) 0.0250(4) Uani d . 1 1
H H5A 0.3831 -0.0220 0.6428 0.030 Uiso calc R 1 1
C C6 0.2890(3) -0.14930(17) 0.52499(18) 0.0216(4) Uani d . 1 1
C C7 0.0985(3) 0.07370(17) 0.33405(18) 0.0225(4) Uani d . 1 1
C C8 0.0876(3) 0.19245(16) 0.34351(18) 0.0221(4) Uani d . 1 1
C C9 0.1800(3) 0.24284(17) 0.46791(19) 0.0256(4) Uani d . 1 1
H H9A 0.1471 0.3197 0.4678 0.038 Uiso calc R 1 1
H H9B 0.3164 0.2353 0.4787 0.038 Uiso calc R 1 1
H H9C 0.1367 0.2063 0.5382 0.038 Uiso calc R 1 1
H H1N1 0.129(4) -0.130(2) 0.344(3) 0.032(7) Uiso d . 1 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'
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
N2 N1 C6 119.79(17)
N2 N1 H1N1 121.9(15)
C6 N1 H1N1 118.0(15)
C7 N2 N1 121.15(18)
C2 C1 C6 119.68(19)
C2 C1 H1A 120.2
C6 C1 H1A 120.2
C3 C2 C1 120.5(2)
C3 C2 H2A 119.8
C1 C2 H2A 119.8
C2 C3 C4 119.25(19)
C2 C3 H3A 120.4
C4 C3 H3A 120.4
C5 C4 C3 121.2(2)
C5 C4 H4A 119.4
C3 C4 H4A 119.4
C4 C5 C6 119.0(2)
C4 C5 H5A 120.5
C6 C5 H5A 120.5
C5 C6 C1 120.37(18)
C5 C6 N1 121.67(18)
C1 C6 N1 117.96(18)
N2 C7 C8 120.84(18)
N2 C7 Cl1 122.96(16)
C8 C7 Cl1 116.16(14)
O1 C8 C7 120.24(18)
O1 C8 C9 122.88(19)
C7 C8 C9 116.87(17)
C8 C9 H9A 109.5
C8 C9 H9B 109.5
H9A C9 H9B 109.5
C8 C9 H9C 109.5
H9A C9 H9C 109.5
H9B C9 H9C 109.5
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
Cl1 C7 1.798(2)
O1 C8 1.223(2)
N1 N2 1.327(2)
N1 C6 1.409(2)
N1 H1N1 1.00(3)
N2 C7 1.279(3)
C1 C2 1.392(3)
C1 C6 1.397(3)
C1 H1A 0.9500
C2 C3 1.391(3)
C2 H2A 0.9500
C3 C4 1.392(3)
C3 H3A 0.9500
C4 C5 1.391(3)
C4 H4A 0.9500
C5 C6 1.397(3)
C5 H5A 0.9500
C7 C8 1.475(3)
C8 C9 1.505(3)
C9 H9A 0.9800
C9 H9B 0.9800
C9 H9C 0.9800
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 H1N1 O1 2_545 0.99(3) 2.01(3) 2.948(2) 157(2) yes
C1 H1A O1 2_545 0.95 2.45 3.237(3) 140 yes
C9 H9B Cg1 3_656 0.98 2.68 3.560(2) 149 yes
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
C6 N1 N2 C7 179.46(17)
C6 C1 C2 C3 0.0(3)
C1 C2 C3 C4 -0.1(3)
C2 C3 C4 C5 0.2(3)
C3 C4 C5 C6 -0.1(3)
C4 C5 C6 C1 -0.1(3)
C4 C5 C6 N1 179.75(18)
C2 C1 C6 C5 0.1(3)
C2 C1 C6 N1 -179.73(17)
N2 N1 C6 C5 -4.6(3)
N2 N1 C6 C1 175.28(17)
N1 N2 C7 C8 -178.98(17)
N1 N2 C7 Cl1 -1.3(3)
N2 C7 C8 O1 179.02(17)
Cl1 C7 C8 O1 1.2(2)
N2 C7 C8 C9 0.5(3)
Cl1 C7 C8 C9 -177.33(13)
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 4647081
