#------------------------------------------------------------------------------
#$Date: 2017-10-13 12:31:46 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201979 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/23/05/2230533.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_2230533
loop_
_publ_author_name
'Lo, Kong Mun'
'Ng, Seik Weng'
_publ_section_title
;
 2-{[2-(4-Chlorophenyl)hydrazinylidene]methyl}phenol
;
_journal_coeditor_code           XU5209
_journal_issue                   6
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o1452
_journal_paper_doi               10.1107/S1600536811017958
_journal_volume                  67
_journal_year                    2011
_chemical_formula_iupac          'C13 H11 Cl N2 O'
_chemical_formula_moiety         'C13 H11 Cl N2 O'
_chemical_formula_sum            'C13 H11 Cl N2 O'
_chemical_formula_weight         246.69
_chemical_name_systematic
;
2-{[2-(4-Chlorophenyl)hydrazinylidene]methyl}phenol
;
_space_group_IT_number           61
_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_Hall  '-P 2ac 2ab'
_symmetry_space_group_name_H-M   'P b c a'
_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                 90.00
_cell_angle_gamma                90.00
_cell_formula_units_Z            8
_cell_length_a                   10.75900(10)
_cell_length_b                   7.31890(10)
_cell_length_c                   28.9222(3)
_cell_measurement_reflns_used    7363
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      28.34
_cell_measurement_theta_min      2.36
_cell_volume                     2277.45(4)
_computing_cell_refinement       'SAINT (Bruker, 2009)'
_computing_data_collection       'APEX2 (Bruker, 2009)'
_computing_data_reduction        'SAINT (Bruker, 2009)'
_computing_molecular_graphics    'X-SEED (Barbour, 2001)'
_computing_publication_material  'publCIF (Westrip, 2010)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      100(2)
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_device_type  'Bruker SMART APEX'
_diffrn_measurement_method       ω
_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  0.0327
_diffrn_reflns_av_sigmaI/netI    0.0201
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       37
_diffrn_reflns_limit_l_min       -37
_diffrn_reflns_number            20107
_diffrn_reflns_theta_full        27.50
_diffrn_reflns_theta_max         27.50
_diffrn_reflns_theta_min         2.36
_diffrn_standards_decay_%        0
_diffrn_standards_interval_count 0
_diffrn_standards_interval_time  0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.318
_exptl_absorpt_correction_T_max  0.9538
_exptl_absorpt_correction_T_min  0.9247
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SADABS; Sheldrick, 1996)'
_exptl_crystal_colour            Colorless
_exptl_crystal_density_diffrn    1.439
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       Block
_exptl_crystal_F_000             1024
_exptl_crystal_size_max          0.25
_exptl_crystal_size_mid          0.25
_exptl_crystal_size_min          0.15
_refine_diff_density_max         0.369
_refine_diff_density_min         -0.185
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.039
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     162
_refine_ls_number_reflns         2614
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.039
_refine_ls_R_factor_all          0.0354
_refine_ls_R_factor_gt           0.0314
_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)+(0.0487P)²+0.9769P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0858
_refine_ls_wR_factor_ref         0.0890
_reflns_number_gt                2326
_reflns_number_total             2614
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            xu5209.cif
_cod_data_source_block           I
_cod_database_code               2230533
_cod_database_fobs_code          2230533
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'x+1/2, -y+1/2, -z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, y, -z-1/2'
'-x-1/2, y-1/2, 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
_atom_site_disorder_assembly
_atom_site_disorder_group
Cl Cl1 0.72028(3) 0.56809(4) 0.484943(10) 0.02413(12) Uani d . 1 1 . .
O O1 0.75260(9) 0.62244(14) 0.75810(3) 0.0202(2) Uani d . 1 1 . .
N N1 0.57723(9) 0.76810(14) 0.70608(3) 0.0160(2) Uani d . 1 1 . .
N N2 0.52407(10) 0.81449(15) 0.66514(4) 0.0192(2) Uani d . 1 1 . .
C C1 0.68256(11) 0.67666(16) 0.79476(4) 0.0158(2) Uani d . 1 1 . .
C C2 0.72583(11) 0.63711(18) 0.83900(4) 0.0183(3) Uani d . 1 1 . .
H H2A 0.8022 0.5739 0.8429 0.022 Uiso calc R 1 1 . .
C C3 0.65750(12) 0.68996(16) 0.87755(4) 0.0197(3) Uani d . 1 1 . .
H H3 0.6883 0.6646 0.9077 0.024 Uiso calc R 1 1 . .
C C4 0.54397(12) 0.77994(17) 0.87237(4) 0.0198(3) Uani d . 1 1 . .
H H4 0.4971 0.8152 0.8987 0.024 Uiso calc R 1 1 . .
C C5 0.50049(12) 0.81715(16) 0.82826(4) 0.0174(2) Uani d . 1 1 . .
H H5 0.4230 0.8778 0.8247 0.021 Uiso calc R 1 1 . .
C C6 0.56790(11) 0.76755(16) 0.78874(4) 0.0150(2) Uani d . 1 1 . .
C C7 0.51856(11) 0.81180(16) 0.74331(4) 0.0157(2) Uani d . 1 1 . .
H H7 0.4414 0.8743 0.7410 0.019 Uiso calc R 1 1 . .
C C8 0.57272(11) 0.75285(16) 0.62353(4) 0.0157(2) Uani d . 1 1 . .
C C9 0.50203(11) 0.77689(17) 0.58344(4) 0.0183(3) Uani d . 1 1 . .
H H9 0.4223 0.8322 0.5854 0.022 Uiso calc R 1 1 . .
C C10 0.54686(12) 0.72102(17) 0.54082(4) 0.0193(3) Uani d . 1 1 . .
H H10 0.4986 0.7382 0.5137 0.023 Uiso calc R 1 1 . .
C C11 0.66308(12) 0.63963(17) 0.53830(4) 0.0180(2) Uani d . 1 1 . .
C C12 0.73438(12) 0.61342(17) 0.57764(4) 0.0182(3) Uani d . 1 1 . .
H H12 0.8137 0.5569 0.5754 0.022 Uiso calc R 1 1 . .
C C13 0.68960(11) 0.66998(16) 0.62040(4) 0.0171(2) Uani d . 1 1 . .
H H13 0.7383 0.6524 0.6474 0.020 Uiso calc R 1 1 . .
H H1 0.7170(18) 0.662(3) 0.7343(7) 0.047(6) Uiso d . 1 1 . .
H H2 0.4532(17) 0.868(3) 0.6662(6) 0.032(5) 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_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle
_geom_angle_publ_flag
C1 O1 H1 . . 106.7(14) ?
C7 N1 N2 . . 117.40(10) ?
N1 N2 C8 . . 121.06(10) ?
N1 N2 H2 . . 117.2(11) ?
C8 N2 H2 . . 121.0(11) ?
O1 C1 C2 . . 118.08(11) ?
O1 C1 C6 . . 121.69(11) ?
C2 C1 C6 . . 120.22(11) ?
C1 C2 C3 . . 120.17(11) ?
C1 C2 H2A . . 119.9 ?
C3 C2 H2A . . 119.9 ?
C2 C3 C4 . . 120.51(11) ?
C2 C3 H3 . . 119.7 ?
C4 C3 H3 . . 119.7 ?
C5 C4 C3 . . 119.15(11) ?
C5 C4 H4 . . 120.4 ?
C3 C4 H4 . . 120.4 ?
C4 C5 C6 . . 121.68(11) ?
C4 C5 H5 . . 119.2 ?
C6 C5 H5 . . 119.2 ?
C5 C6 C1 . . 118.27(11) ?
C5 C6 C7 . . 119.37(11) ?
C1 C6 C7 . . 122.36(11) ?
N1 C7 C6 . . 121.41(11) ?
N1 C7 H7 . . 119.3 ?
C6 C7 H7 . . 119.3 ?
N2 C8 C9 . . 118.24(11) ?
N2 C8 C13 . . 122.42(11) ?
C9 C8 C13 . . 119.33(11) ?
C10 C9 C8 . . 120.76(11) ?
C10 C9 H9 . . 119.6 ?
C8 C9 H9 . . 119.6 ?
C9 C10 C11 . . 119.17(11) ?
C9 C10 H10 . . 120.4 ?
C11 C10 H10 . . 120.4 ?
C10 C11 C12 . . 121.02(11) ?
C10 C11 Cl1 . . 119.62(9) ?
C12 C11 Cl1 . . 119.36(10) ?
C11 C12 C13 . . 119.83(12) ?
C11 C12 H12 . . 120.1 ?
C13 C12 H12 . . 120.1 ?
C12 C13 C8 . . 119.88(11) ?
C12 C13 H13 . . 120.1 ?
C8 C13 H13 . . 120.1 ?
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 C11 . 1.7418(12) ?
O1 C1 . 1.3600(15) ?
O1 H1 . 0.84(2) ?
N1 C7 . 1.2883(15) ?
N1 N2 . 1.3580(14) ?
N2 C8 . 1.3878(15) ?
N2 H2 . 0.859(18) ?
C1 C2 . 1.3919(17) ?
C1 C6 . 1.4123(17) ?
C2 C3 . 1.3905(18) ?
C2 H2A . 0.9500 ?
C3 C4 . 1.3958(19) ?
C3 H3 . 0.9500 ?
C4 C5 . 1.3859(17) ?
C4 H4 . 0.9500 ?
C5 C6 . 1.4014(16) ?
C5 H5 . 0.9500 ?
C6 C7 . 1.4539(16) ?
C7 H7 . 0.9500 ?
C8 C9 . 1.3978(16) ?
C8 C13 . 1.3991(17) ?
C9 C10 . 1.3855(17) ?
C9 H9 . 0.9500 ?
C10 C11 . 1.3870(18) ?
C10 H10 . 0.9500 ?
C11 C12 . 1.3857(18) ?
C12 C13 . 1.3901(17) ?
C12 H12 . 0.9500 ?
C13 H13 . 0.9500 ?
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
O1 H1 N1 . 0.84(2) 1.88(2) 2.6382(13) 149.8(19) yes
N2 H2 Cg1 4_656 0.859(18) 2.73(2) 3.3675(12) 132.3(17) 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_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion
_geom_torsion_publ_flag
C7 N1 N2 C8 . . . . -171.80(11) ?
O1 C1 C2 C3 . . . . 179.94(11) ?
C6 C1 C2 C3 . . . . -1.21(19) ?
C1 C2 C3 C4 . . . . 1.21(19) ?
C2 C3 C4 C5 . . . . -0.44(18) ?
C3 C4 C5 C6 . . . . -0.32(18) ?
C4 C5 C6 C1 . . . . 0.31(18) ?
C4 C5 C6 C7 . . . . -179.31(11) ?
O1 C1 C6 C5 . . . . 179.26(11) ?
C2 C1 C6 C5 . . . . 0.46(18) ?
O1 C1 C6 C7 . . . . -1.13(18) ?
C2 C1 C6 C7 . . . . -179.93(11) ?
N2 N1 C7 C6 . . . . 179.85(10) ?
C5 C6 C7 N1 . . . . -179.72(11) ?
C1 C6 C7 N1 . . . . 0.68(18) ?
N1 N2 C8 C9 . . . . 168.57(11) ?
N1 N2 C8 C13 . . . . -12.10(18) ?
N2 C8 C9 C10 . . . . 178.83(12) ?
C13 C8 C9 C10 . . . . -0.52(18) ?
C8 C9 C10 C11 . . . . 0.32(19) ?
C9 C10 C11 C12 . . . . 0.10(19) ?
C9 C10 C11 Cl1 . . . . 179.78(10) ?
C10 C11 C12 C13 . . . . -0.30(19) ?
Cl1 C11 C12 C13 . . . . -179.99(10) ?
C11 C12 C13 C8 . . . . 0.10(18) ?
N2 C8 C13 C12 . . . . -179.01(11) ?
C9 C8 C13 C12 . . . . 0.31(18) ?
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 12527878
