#------------------------------------------------------------------------------
#$Date: 2017-10-13 10:03:29 +0200 (vie 13 de oct de 2017) $
#$Revision: 201974 $
#$URL: svn://www.crystallography.net/cod/cif/2/21/21/2212138.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_2212138
loop_
_publ_author_name
'Jian-Guo Chang'
'Ying Cheng'
'Xi-Tao He'
_publ_section_title
N'-[(1E)-(5-Chloro-2-hydroxyphenyl)(phenyl)methylene]-2-hydroxybenzohydrazide
_journal_coeditor_code           DN2109
_journal_issue                   2
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o474
_journal_page_last               o475
_journal_paper_doi               10.1107/S1600536806055115
_journal_volume                  63
_journal_year                    2007
_chemical_formula_iupac          'C20 H15 Cl N2 O3'
_chemical_formula_moiety         'C20 H15 Cl N2 O3'
_chemical_formula_sum            'C20 H15 Cl N2 O3'
_chemical_formula_weight         366.79
_chemical_name_systematic
;
N'-[(1E)-(5-Chloro-2-hydroxyphenyl)(phenyl)methylene]-2-hydroxybenzohydrazide
;
_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
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_formula_units_Z            8
_cell_length_a                   15.3237(6)
_cell_length_b                   12.0171(5)
_cell_length_c                   20.0773(8)
_cell_measurement_reflns_used    5275
_cell_measurement_temperature    273(2)
_cell_measurement_theta_max      21.52
_cell_measurement_theta_min      2.38
_cell_volume                     3697.2(3)
_computing_cell_refinement       'SAINT (Siemens, 1996)'
_computing_data_collection       'SMART (Siemens, 1996)'
_computing_data_reduction        SAINT
_computing_molecular_graphics
'SHELXTL (Sheldrick, 1997b) and PLATON (Spek, 2003)'
_computing_publication_material  SHELXTL
_computing_structure_refinement  'SHELXL97 (Sheldrick, 1997a)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 1997a)'
_diffrn_ambient_temperature      273(2)
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type  'Bruker SMART CCD area-detector'
_diffrn_measurement_method       'φ and 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  0.0577
_diffrn_reflns_av_sigmaI/netI    0.0237
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_h_min       -18
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_number            39233
_diffrn_reflns_theta_full        25.00
_diffrn_reflns_theta_max         25.00
_diffrn_reflns_theta_min         2.03
_exptl_absorpt_coefficient_mu    0.228
_exptl_absorpt_correction_T_max  0.9776
_exptl_absorpt_correction_T_min  0.9244
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SADABS; Sheldrick, 1996)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.318
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             1520
_exptl_crystal_size_max          0.45
_exptl_crystal_size_mid          0.24
_exptl_crystal_size_min          0.20
_refine_diff_density_max         0.119
_refine_diff_density_min         -0.218
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.000
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     237
_refine_ls_number_reflns         3248
_refine_ls_number_restraints     18
_refine_ls_restrained_S_all      0.997
_refine_ls_R_factor_all          0.0647
_refine_ls_R_factor_gt           0.0395
_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)+(0.0507P)²+1.2845P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0967
_refine_ls_wR_factor_ref         0.1152
_reflns_number_gt                2261
_reflns_number_total             3248
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            dn2109.cif
_cod_data_source_block           I
_cod_database_code               2212138
_cod_database_fobs_code          2212138
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'-x, y+1/2, -z+1/2'
'x+1/2, -y+1/2, -z'
'-x, -y, -z'
'x-1/2, y, -z-1/2'
'x, -y-1/2, z-1/2'
'-x-1/2, y-1/2, z'
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
Cl Cl1 1.09963(5) 0.85633(6) 0.30089(4) 0.0975(3) Uani d . 1
O O1 0.99237(12) 1.16483(12) 0.09131(8) 0.0717(5) Uani d . 1
H H1 0.9591 1.1359 0.0644 0.107 Uiso calc R 1
O O2 0.84619(9) 1.14393(11) -0.05196(7) 0.0563(4) Uani d . 1
O O3 0.73116(14) 0.83443(13) -0.05047(9) 0.0882(6) Uani d . 1
H H3 0.7039 0.7763 -0.0555 0.132 Uiso calc R 1
N N1 0.90070(10) 1.00781(13) 0.04214(8) 0.0498(4) Uani d . 1
N N2 0.84440(10) 0.97365(13) -0.00650(8) 0.0499(4) Uani d . 1
H H2 0.8267 0.9058 -0.0080 0.060 Uiso calc R 1
C C1 1.01537(14) 1.08944(17) 0.13786(10) 0.0539(5) Uani d . 1
C C2 0.98516(12) 0.97898(15) 0.13790(9) 0.0454(5) Uani d . 1
C C3 1.01305(13) 0.90851(17) 0.18889(9) 0.0507(5) Uani d . 1
H H3A 0.9939 0.8351 0.1898 0.061 Uiso calc R 1
C C4 1.06837(14) 0.94629(19) 0.23773(10) 0.0594(6) Uani d . 1
C C5 1.09790(15) 1.0544(2) 0.23730(11) 0.0680(6) Uani d . 1
H H5 1.1353 1.0794 0.2706 0.082 Uiso calc R 1
C C6 1.07182(15) 1.12493(19) 0.18764(11) 0.0652(6) Uani d . 1
H H6 1.0922 1.1978 0.1872 0.078 Uiso calc R 1
C C7 0.92515(12) 0.93681(16) 0.08668(9) 0.0450(5) Uani d . 1
C C8 0.89440(13) 0.81937(16) 0.08701(9) 0.0480(5) Uani d . 1
C C9 0.81224(15) 0.7930(2) 0.10964(12) 0.0711(7) Uani d . 1
H H9 0.7767 0.8487 0.1270 0.085 Uiso calc R 1
C C10 0.78195(19) 0.6851(3) 0.10696(16) 0.0918(9) Uani d . 1
H H10 0.7264 0.6682 0.1226 0.110 Uiso calc R 1
C C11 0.8329(2) 0.6040(3) 0.08172(15) 0.0930(10) Uani d U 1
H H11 0.8119 0.5316 0.0791 0.112 Uiso calc R 1
C C12 0.9149(2) 0.6275(2) 0.06003(15) 0.0971(9) Uani d U 1
H H12 0.9502 0.5708 0.0437 0.116 Uiso calc R 1
C C13 0.94613(17) 0.73602(19) 0.06226(12) 0.0720(7) Uani d U 1
H H13 1.0020 0.7521 0.0470 0.086 Uiso calc R 1
C C14 0.81715(13) 1.04834(16) -0.05220(9) 0.0459(5) Uani d . 1
C C15 0.75267(13) 1.00895(15) -0.10192(9) 0.0469(5) Uani d . 1
C C16 0.71261(14) 0.90519(16) -0.10126(10) 0.0557(5) Uani d . 1
C C17 0.65505(15) 0.87517(19) -0.15125(12) 0.0679(6) Uani d . 1
H H17 0.6283 0.8057 -0.1501 0.081 Uiso calc R 1
C C18 0.63731(17) 0.9473(2) -0.20245(13) 0.0760(7) Uani d . 1
H H18 0.5992 0.9265 -0.2362 0.091 Uiso calc R 1
C C19 0.67607(17) 1.0507(2) -0.20376(12) 0.0774(7) Uani d . 1
H H19 0.6639 1.0999 -0.2383 0.093 Uiso calc R 1
C C20 0.73247(15) 1.08075(18) -0.15421(11) 0.0618(6) Uani d . 1
H H20 0.7580 1.1509 -0.1554 0.074 Uiso calc R 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
C1 O1 H1 109.5
C16 O3 H3 109.5
C7 N1 N2 118.66(16)
C14 N2 N1 118.78(16)
C14 N2 H2 120.6
N1 N2 H2 120.6
O1 C1 C6 117.08(19)
O1 C1 C2 123.27(18)
C6 C1 C2 119.6(2)
C3 C2 C1 118.19(18)
C3 C2 C7 119.71(17)
C1 C2 C7 122.09(17)
C4 C3 C2 120.80(19)
C4 C3 H3A 119.6
C2 C3 H3A 119.6
C3 C4 C5 120.7(2)
C3 C4 Cl1 119.11(17)
C5 C4 Cl1 120.16(17)
C6 C5 C4 119.6(2)
C6 C5 H5 120.2
C4 C5 H5 120.2
C5 C6 C1 121.1(2)
C5 C6 H6 119.5
C1 C6 H6 119.5
N1 C7 C2 115.99(17)
N1 C7 C8 122.53(17)
C2 C7 C8 121.48(16)
C13 C8 C9 118.8(2)
C13 C8 C7 120.56(19)
C9 C8 C7 120.64(19)
C8 C9 C10 120.8(3)
C8 C9 H9 119.6
C10 C9 H9 119.6
C11 C10 C9 120.0(3)
C11 C10 H10 120.0
C9 C10 H10 120.0
C10 C11 C12 120.4(3)
C10 C11 H11 119.8
C12 C11 H11 119.8
C11 C12 C13 120.2(3)
C11 C12 H12 119.9
C13 C12 H12 119.9
C8 C13 C12 119.9(3)
C8 C13 H13 120.1
C12 C13 H13 120.1
O2 C14 N2 120.37(18)
O2 C14 C15 122.77(17)
N2 C14 C15 116.85(17)
C16 C15 C20 117.68(18)
C16 C15 C14 125.06(17)
C20 C15 C14 117.24(18)
O3 C16 C17 120.98(19)
O3 C16 C15 118.46(18)
C17 C16 C15 120.56(18)
C18 C17 C16 120.3(2)
C18 C17 H17 119.8
C16 C17 H17 119.8
C17 C18 C19 119.9(2)
C17 C18 H18 120.0
C19 C18 H18 120.0
C20 C19 C18 119.8(2)
C20 C19 H19 120.1
C18 C19 H19 120.1
C19 C20 C15 121.7(2)
C19 C20 H20 119.2
C15 C20 H20 119.2
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
Cl1 C4 1.734(2)
O1 C1 1.349(2)
O1 H1 0.8200
O2 C14 1.232(2)
O3 C16 1.358(2)
O3 H3 0.8200
N1 C7 1.292(2)
N1 N2 1.366(2)
N2 C14 1.350(2)
N2 H2 0.8600
C1 C6 1.389(3)
C1 C2 1.406(3)
C2 C3 1.396(3)
C2 C7 1.470(3)
C3 C4 1.373(3)
C3 H3A 0.9300
C4 C5 1.376(3)
C5 C6 1.368(3)
C5 H5 0.9300
C6 H6 0.9300
C7 C8 1.488(3)
C8 C13 1.371(3)
C8 C9 1.375(3)
C9 C10 1.379(4)
C9 H9 0.9300
C10 C11 1.347(4)
C10 H10 0.9300
C11 C12 1.360(4)
C11 H11 0.9300
C12 C13 1.390(4)
C12 H12 0.9300
C13 H13 0.9300
C14 C15 1.482(3)
C15 C16 1.390(3)
C15 C20 1.394(3)
C16 C17 1.384(3)
C17 C18 1.372(3)
C17 H17 0.9300
C18 C19 1.377(3)
C18 H18 0.9300
C19 C20 1.366(3)
C19 H19 0.9300
C20 H20 0.9300
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 . 0.820 1.835 2.5510(10) 145.05 y
N2 H2 O3 . 0.860 1.899 2.5670(10) 133.43 y
O3 H3 O2 8_755 0.820 1.768 2.5780(10) 169.23 y
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
C7 N1 N2 C14 178.47(17)
O1 C1 C2 C3 -179.66(19)
C6 C1 C2 C3 0.4(3)
O1 C1 C2 C7 -0.2(3)
C6 C1 C2 C7 179.79(18)
C1 C2 C3 C4 0.1(3)
C7 C2 C3 C4 -179.30(18)
C2 C3 C4 C5 -0.3(3)
C2 C3 C4 Cl1 178.83(15)
C3 C4 C5 C6 0.0(4)
Cl1 C4 C5 C6 -179.15(18)
C4 C5 C6 C1 0.5(4)
O1 C1 C6 C5 179.3(2)
C2 C1 C6 C5 -0.7(3)
N2 N1 C7 C2 -179.53(15)
N2 N1 C7 C8 0.0(3)
C3 C2 C7 N1 178.37(17)
C1 C2 C7 N1 -1.0(3)
C3 C2 C7 C8 -1.2(3)
C1 C2 C7 C8 179.41(18)
N1 C7 C8 C13 100.0(2)
C2 C7 C8 C13 -80.5(2)
N1 C7 C8 C9 -77.3(3)
C2 C7 C8 C9 102.2(2)
C13 C8 C9 C10 -0.6(3)
C7 C8 C9 C10 176.8(2)
C8 C9 C10 C11 -0.3(4)
C9 C10 C11 C12 1.3(4)
C10 C11 C12 C13 -1.5(4)
C9 C8 C13 C12 0.4(3)
C7 C8 C13 C12 -177.0(2)
C11 C12 C13 C8 0.6(4)
N1 N2 C14 O2 3.8(3)
N1 N2 C14 C15 -176.99(16)
O2 C14 C15 C16 -174.5(2)
N2 C14 C15 C16 6.3(3)
O2 C14 C15 C20 7.1(3)
N2 C14 C15 C20 -172.09(18)
C20 C15 C16 O3 -179.6(2)
C14 C15 C16 O3 2.0(3)
C20 C15 C16 C17 0.3(3)
C14 C15 C16 C17 -178.1(2)
O3 C16 C17 C18 -179.6(2)
C15 C16 C17 C18 0.5(4)
C16 C17 C18 C19 -0.8(4)
C17 C18 C19 C20 0.4(4)
C18 C19 C20 C15 0.4(4)
C16 C15 C20 C19 -0.7(3)
C14 C15 C20 C19 177.8(2)
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 21185662
