#------------------------------------------------------------------------------
#$Date: 2017-10-13 12:31:46 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201979 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/23/43/2234369.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_2234369
loop_
_publ_author_name
'Xu, Huanzhi'
'Sun, Jingya'
_publ_section_title
;
 N'-(3,5-Dichloro-2-hydroxybenzylidene)-4-(dimethylamino)benzohydrazide
 methanol monosolvate
;
_journal_coeditor_code           QM2057
_journal_issue                   4
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o1042
_journal_paper_doi               10.1107/S1600536812010148
_journal_volume                  68
_journal_year                    2012
_chemical_formula_iupac          'C16 H15 Cl2 N3 O2, C H4 O'
_chemical_formula_moiety         'C16 H15 Cl2 N3 O2, C H4 O'
_chemical_formula_sum            'C17 H19 Cl2 N3 O3'
_chemical_formula_weight         384.25
_chemical_name_systematic
;
N'-(3,5-Dichloro-2-hydroxybenzylidene)-4-(dimethylamino)benzohydrazide
methanol monosolvate
;
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2yn'
_symmetry_space_group_name_H-M   'P 1 21/n 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                 103.076(2)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   7.6498(15)
_cell_length_b                   14.338(3)
_cell_length_c                   16.884(2)
_cell_measurement_reflns_used    2546
_cell_measurement_temperature    298(2)
_cell_measurement_theta_max      28.3
_cell_measurement_theta_min      2.5
_cell_volume                     1803.9(6)
_computing_cell_refinement       'SAINT (Bruker, 2007)'
_computing_data_collection       'SMART (Bruker, 2007)'
_computing_data_reduction        'SAINT (Bruker, 2007)'
_computing_molecular_graphics    'SHELXTL (Sheldrick, 2008)'
_computing_publication_material  'SHELXTL (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXTL (Sheldrick, 2008)'
_computing_structure_solution    'SHELXTL (Sheldrick, 2008)'
_diffrn_ambient_temperature      298(2)
_diffrn_measured_fraction_theta_full 0.961
_diffrn_measured_fraction_theta_max 0.961
_diffrn_measurement_device_type  'Bruker SMART CCD area-detector'
_diffrn_measurement_method       '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  0.0721
_diffrn_reflns_av_sigmaI/netI    0.1035
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            8311
_diffrn_reflns_theta_full        25.49
_diffrn_reflns_theta_max         25.49
_diffrn_reflns_theta_min         2.48
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.381
_exptl_absorpt_correction_T_max  0.9629
_exptl_absorpt_correction_T_min  0.9521
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SADABS; Bruker, 2001)'
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.415
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             800
_exptl_crystal_size_max          0.13
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.10
_refine_diff_density_max         0.236
_refine_diff_density_min         -0.217
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.031
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     231
_refine_ls_number_reflns         3238
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.031
_refine_ls_R_factor_all          0.1423
_refine_ls_R_factor_gt           0.0785
_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)+(0.0664P)²+0.8315P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1564
_refine_ls_wR_factor_ref         0.1802
_reflns_number_gt                1790
_reflns_number_total             3238
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            qm2057.cif
_cod_data_source_block           I
_cod_original_cell_volume        1803.8(5)
_cod_original_sg_symbol_H-M      'P 21/n'
_cod_database_code               2234369
_cod_database_fobs_code          2234369
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -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 0.4325(2) 0.29209(10) 0.15198(9) 0.0674(5) Uani d . 1 1
Cl Cl2 0.4175(2) 0.65692(11) 0.07222(9) 0.0719(5) Uani d . 1 1
N N1 0.2957(5) 0.4874(3) 0.4015(2) 0.0450(10) Uani d . 1 1
N N2 0.2686(5) 0.5167(3) 0.4749(2) 0.0431(10) Uani d . 1 1
H H2 0.2702 0.5751 0.4864 0.052 Uiso calc R 1 1
N N3 0.1064(6) 0.5808(3) 0.8296(2) 0.0490(11) Uani d . 1 1
O O1 0.3448(5) 0.3581(2) 0.3007(2) 0.0564(10) Uani d . 1 1
H H1 0.3013 0.3780 0.3376 0.085 Uiso calc R 1 1
O O2 0.2453(5) 0.3677(2) 0.5161(2) 0.0530(10) Uani d . 1 1
O O3 0.5727(5) 0.3035(2) 0.4941(2) 0.0608(10) Uani d . 1 1
H H3 0.4685 0.3145 0.4960 0.091 Uiso calc R 1 1
C C1 0.3425(6) 0.5229(3) 0.2711(3) 0.0394(12) Uani d . 1 1
C C2 0.3621(6) 0.4282(3) 0.2505(3) 0.0420(12) Uani d . 1 1
C C3 0.4009(6) 0.4078(4) 0.1756(3) 0.0483(13) Uani d . 1 1
C C4 0.4178(6) 0.4767(4) 0.1208(3) 0.0463(13) Uani d . 1 1
H H4 0.4441 0.4616 0.0712 0.056 Uiso calc R 1 1
C C5 0.3950(6) 0.5682(4) 0.1411(3) 0.0481(13) Uani d . 1 1
C C6 0.3577(6) 0.5909(4) 0.2145(3) 0.0474(13) Uani d . 1 1
H H6 0.3422 0.6532 0.2266 0.057 Uiso calc R 1 1
C C7 0.3097(6) 0.5495(3) 0.3482(3) 0.0407(12) Uani d . 1 1
H H7 0.2984 0.6123 0.3599 0.049 Uiso calc R 1 1
C C8 0.2386(6) 0.4510(4) 0.5302(3) 0.0388(12) Uani d . 1 1
C C9 0.1976(6) 0.4892(3) 0.6054(3) 0.0363(11) Uani d . 1 1
C C10 0.1902(6) 0.4268(3) 0.6673(3) 0.0408(12) Uani d . 1 1
H H10 0.2087 0.3637 0.6592 0.049 Uiso calc R 1 1
C C11 0.1562(6) 0.4551(3) 0.7403(3) 0.0436(12) Uani d . 1 1
H H11 0.1497 0.4109 0.7799 0.052 Uiso calc R 1 1
C C12 0.1311(6) 0.5505(3) 0.7556(3) 0.0358(11) Uani d . 1 1
C C13 0.1359(6) 0.6129(3) 0.6922(3) 0.0455(12) Uani d . 1 1
H H13 0.1173 0.6761 0.6996 0.055 Uiso calc R 1 1
C C14 0.1672(6) 0.5830(3) 0.6193(3) 0.0427(12) Uani d . 1 1
H H14 0.1681 0.6263 0.5784 0.051 Uiso calc R 1 1
C C15 0.0961(8) 0.5155(4) 0.8937(3) 0.0577(15) Uani d . 1 1
H H15A 0.0012 0.4716 0.8743 0.087 Uiso calc R 1 1
H H15B 0.0723 0.5487 0.9395 0.087 Uiso calc R 1 1
H H15C 0.2080 0.4827 0.9098 0.087 Uiso calc R 1 1
C C16 0.0752(7) 0.6783(4) 0.8461(3) 0.0591(15) Uani d . 1 1
H H16A 0.1787 0.7145 0.8425 0.089 Uiso calc R 1 1
H H16B 0.0538 0.6841 0.8997 0.089 Uiso calc R 1 1
H H16C -0.0274 0.7007 0.8069 0.089 Uiso calc R 1 1
C C17 0.5794(7) 0.2197(4) 0.4506(3) 0.0619(16) Uani d . 1 1
H H17A 0.7002 0.1964 0.4626 0.093 Uiso calc R 1 1
H H17B 0.5411 0.2315 0.3934 0.093 Uiso calc R 1 1
H H17C 0.5016 0.1743 0.4665 0.093 Uiso calc R 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
C7 N1 N2 118.3(4)
N1 N2 C8 119.1(4)
N1 N2 H2 120.5
C8 N2 H2 120.5
C12 N3 C15 121.1(4)
C12 N3 C16 122.6(4)
C15 N3 C16 116.1(4)
C2 O1 H1 109.5
C17 O3 H3 109.5
C6 C1 C2 118.3(4)
C6 C1 C7 119.8(5)
C2 C1 C7 121.9(5)
O1 C2 C3 119.2(5)
O1 C2 C1 122.1(4)
C3 C2 C1 118.7(5)
C4 C3 C2 122.0(5)
C4 C3 Cl1 119.4(4)
C2 C3 Cl1 118.6(4)
C5 C4 C3 118.6(5)
C5 C4 H4 120.7
C3 C4 H4 120.7
C6 C5 C4 120.9(5)
C6 C5 Cl2 119.9(4)
C4 C5 Cl2 119.2(4)
C5 C6 C1 121.5(5)
C5 C6 H6 119.3
C1 C6 H6 119.3
N1 C7 C1 120.7(4)
N1 C7 H7 119.7
C1 C7 H7 119.7
O2 C8 N2 120.9(4)
O2 C8 C9 123.7(4)
N2 C8 C9 115.4(4)
C10 C9 C14 117.3(4)
C10 C9 C8 117.4(4)
C14 C9 C8 125.3(4)
C11 C10 C9 122.2(4)
C11 C10 H10 118.9
C9 C10 H10 118.9
C10 C11 C12 120.6(4)
C10 C11 H11 119.7
C12 C11 H11 119.7
N3 C12 C13 121.7(4)
N3 C12 C11 121.6(4)
C13 C12 C11 116.7(4)
C14 C13 C12 121.6(4)
C14 C13 H13 119.2
C12 C13 H13 119.2
C13 C14 C9 121.5(5)
C13 C14 H14 119.3
C9 C14 H14 119.3
N3 C15 H15A 109.5
N3 C15 H15B 109.5
H15A C15 H15B 109.5
N3 C15 H15C 109.5
H15A C15 H15C 109.5
H15B C15 H15C 109.5
N3 C16 H16A 109.5
N3 C16 H16B 109.5
H16A C16 H16B 109.5
N3 C16 H16C 109.5
H16A C16 H16C 109.5
H16B C16 H16C 109.5
O3 C17 H17A 109.5
O3 C17 H17B 109.5
H17A C17 H17B 109.5
O3 C17 H17C 109.5
H17A C17 H17C 109.5
H17B C17 H17C 109.5
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
Cl1 C3 1.736(5)
Cl2 C5 1.758(5)
N1 C7 1.288(6)
N1 N2 1.367(5)
N2 C8 1.381(6)
N2 H2 0.8600
N3 C12 1.374(6)
N3 C15 1.447(6)
N3 C16 1.456(6)
O1 C2 1.342(5)
O1 H1 0.8200
O2 C8 1.222(5)
O3 C17 1.415(6)
O3 H3 0.8200
C1 C6 1.388(6)
C1 C2 1.417(6)
C1 C7 1.433(6)
C2 C3 1.393(6)
C3 C4 1.379(7)
C4 C5 1.378(7)
C4 H4 0.9300
C5 C6 1.372(7)
C6 H6 0.9300
C7 H7 0.9300
C8 C9 1.480(6)
C9 C10 1.387(6)
C9 C14 1.394(6)
C10 C11 1.378(6)
C10 H10 0.9300
C11 C12 1.414(6)
C11 H11 0.9300
C12 C13 1.402(6)
C13 C14 1.374(6)
C13 H13 0.9300
C14 H14 0.9300
C15 H15A 0.9600
C15 H15B 0.9600
C15 H15C 0.9600
C16 H16A 0.9600
C16 H16B 0.9600
C16 H16C 0.9600
C17 H17A 0.9600
C17 H17B 0.9600
C17 H17C 0.9600
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
N2 H2 O3 3_666 0.86 2.10 2.848(5) 145.3
O1 H1 N1 . 0.82 1.91 2.600(5) 141.2
O3 H3 O2 . 0.82 1.97 2.771(5) 165.9
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 30657634
