#------------------------------------------------------------------------------
#$Date: 2016-02-20 18:35:30 +0200 (Sat, 20 Feb 2016) $
#$Revision: 176787 $
#$URL: svn://www.crystallography.net/cod/cif/2/21/91/2219153.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_2219153
loop_
_publ_author_name
'Zhou, Zhi'
_publ_section_title
;
 N'-(2-Chloro-5-nitrobenzylidene)-3-hydroxybenzohydrazide
 methanol solvate
;
_journal_coeditor_code           RZ2226
_journal_issue                   8
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o1383
_journal_paper_doi               10.1107/S1600536808019636
_journal_volume                  64
_journal_year                    2008
_chemical_formula_iupac          'C14 H10 Cl N3 O4, C H4 O'
_chemical_formula_moiety         'C14 H10 Cl N3 O4, C H4 O'
_chemical_formula_sum            'C15 H14 Cl N3 O5'
_chemical_formula_weight         351.74
_chemical_name_systematic
;
N'-(2-Chloro-5-nitrobenzylidene)-3-hydroxybenzohydrazide
methanol solvate
;
_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                 99.886(2)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   7.716(3)
_cell_length_b                   11.945(2)
_cell_length_c                   17.650(3)
_cell_measurement_reflns_used    2947
_cell_measurement_temperature    298(2)
_cell_measurement_theta_max      24.5
_cell_measurement_theta_min      2.3
_cell_volume                     1602.6(7)
_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 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device_type  'Bruker SMART CCD area-detector'
_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  0.0335
_diffrn_reflns_av_sigmaI/netI    0.0323
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_number            12656
_diffrn_reflns_theta_full        26.50
_diffrn_reflns_theta_max         26.50
_diffrn_reflns_theta_min         2.07
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.270
_exptl_absorpt_correction_T_max  0.9430
_exptl_absorpt_correction_T_min  0.9307
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SADABS; Bruker, 2001)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.458
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             728
_exptl_crystal_size_max          0.27
_exptl_crystal_size_mid          0.23
_exptl_crystal_size_min          0.22
_refine_diff_density_max         0.180
_refine_diff_density_min         -0.219
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.013
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     223
_refine_ls_number_reflns         3316
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.013
_refine_ls_R_factor_all          0.0659
_refine_ls_R_factor_gt           0.0447
_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)+(0.0596P)²+0.2859P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1091
_refine_ls_wR_factor_ref         0.1213
_reflns_number_gt                2396
_reflns_number_total             3316
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            rz2226.cif
_cod_data_source_block           I
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               2219153
_cod_database_fobs_code          2219153
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
Cl Cl1 0.27705(9) 0.68944(5) 0.42450(4) 0.0774(2) Uani d . 1
O O1 -0.1188(3) 1.16001(18) 0.30340(10) 0.0978(7) Uani d . 1
O O2 0.0033(3) 1.21390(16) 0.41618(12) 0.0859(6) Uani d . 1
O O3 0.4707(2) 1.09327(11) 0.70885(8) 0.0623(4) Uani d . 1
O O4 0.6995(2) 0.71117(11) 0.91382(8) 0.0607(4) Uani d . 1
H H4 0.6479 0.6690 0.8808 0.091 Uiso calc R 1
O O5 0.6192(3) 0.69826(13) 0.66034(11) 0.0897(6) Uani d . 1
H H5 0.5907 0.6645 0.6968 0.135 Uiso calc R 1
N N1 -0.0240(3) 1.14400(19) 0.36561(12) 0.0652(5) Uani d . 1
N N2 0.3857(2) 0.95587(12) 0.58923(8) 0.0428(4) Uani d . 1
N N3 0.4964(2) 0.92397(13) 0.65533(9) 0.0424(4) Uani d . 1
C C1 0.2405(2) 0.90699(16) 0.46380(10) 0.0439(5) Uani d . 1
C C2 0.1934(3) 0.82357(18) 0.40857(12) 0.0534(5) Uani d . 1
C C3 0.0788(3) 0.8448(2) 0.34054(13) 0.0684(7) Uani d . 1
H H3 0.0502 0.7880 0.3045 0.082 Uiso calc R 1
C C4 0.0082(3) 0.9485(2) 0.32639(12) 0.0663(7) Uani d . 1
H H4A -0.0690 0.9633 0.2810 0.080 Uiso calc R 1
C C5 0.0531(3) 1.03136(19) 0.38052(11) 0.0533(5) Uani d . 1
C C6 0.1661(3) 1.01296(17) 0.44857(10) 0.0468(5) Uani d . 1
H H6 0.1927 1.0705 0.4841 0.056 Uiso calc R 1
C C7 0.3601(3) 0.88397(16) 0.53602(11) 0.0460(5) Uani d . 1
H H7 0.4179 0.8154 0.5428 0.055 Uiso calc R 1
C C8 0.5280(2) 0.99647(15) 0.71415(10) 0.0429(4) Uani d . 1
C C9 0.6354(2) 0.95567(15) 0.78653(10) 0.0409(4) Uani d . 1
C C10 0.6158(2) 0.84831(15) 0.81342(10) 0.0414(4) Uani d . 1
H H10 0.5366 0.7992 0.7849 0.050 Uiso calc R 1
C C11 0.7141(3) 0.81385(16) 0.88285(11) 0.0451(5) Uani d . 1
C C12 0.8325(3) 0.88781(18) 0.92424(11) 0.0536(5) Uani d . 1
H H12 0.9003 0.8652 0.9704 0.064 Uiso calc R 1
C C13 0.8499(3) 0.99430(19) 0.89738(12) 0.0591(6) Uani d . 1
H H13 0.9295 1.0432 0.9259 0.071 Uiso calc R 1
C C14 0.7518(3) 1.03021(17) 0.82898(11) 0.0511(5) Uani d . 1
H H14 0.7633 1.1029 0.8116 0.061 Uiso calc R 1
C C15 0.6536(4) 0.6218(2) 0.60542(17) 0.0899(9) Uani d . 1
H H15A 0.6769 0.6613 0.5609 0.135 Uiso calc R 1
H H15B 0.5535 0.5739 0.5911 0.135 Uiso calc R 1
H H15C 0.7542 0.5775 0.6263 0.135 Uiso calc R 1
H H3B 0.538(3) 0.862(2) 0.6593(14) 0.080 Uiso d . 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
C11 O4 H4 109.5
C15 O5 H5 109.5
O2 N1 O1 123.6(2)
O2 N1 C5 118.83(18)
O1 N1 C5 117.5(2)
C7 N2 N3 115.93(16)
C8 N3 N2 118.75(15)
C8 N3 H3B 120.6(18)
N2 N3 H3B 120.6(18)
C6 C1 C2 117.57(18)
C6 C1 C7 120.92(17)
C2 C1 C7 121.49(18)
C3 C2 C1 121.6(2)
C3 C2 Cl1 118.32(17)
C1 C2 Cl1 120.09(16)
C4 C3 C2 120.1(2)
C4 C3 H3 119.9
C2 C3 H3 119.9
C3 C4 C5 118.8(2)
C3 C4 H4A 120.6
C5 C4 H4A 120.6
C6 C5 C4 122.5(2)
C6 C5 N1 118.48(19)
C4 C5 N1 119.0(2)
C5 C6 C1 119.39(19)
C5 C6 H6 120.3
C1 C6 H6 120.3
N2 C7 C1 120.94(18)
N2 C7 H7 119.5
C1 C7 H7 119.5
O3 C8 N3 122.02(17)
O3 C8 C9 120.89(16)
N3 C8 C9 117.09(16)
C10 C9 C14 120.50(17)
C10 C9 C8 121.50(16)
C14 C9 C8 117.94(17)
C9 C10 C11 120.11(17)
C9 C10 H10 119.9
C11 C10 H10 119.9
O4 C11 C12 117.23(17)
O4 C11 C10 123.60(17)
C12 C11 C10 119.16(18)
C13 C12 C11 120.26(18)
C13 C12 H12 119.9
C11 C12 H12 119.9
C12 C13 C14 121.29(18)
C12 C13 H13 119.4
C14 C13 H13 119.4
C13 C14 C9 118.66(19)
C13 C14 H14 120.7
C9 C14 H14 120.7
O5 C15 H15A 109.5
O5 C15 H15B 109.5
H15A C15 H15B 109.5
O5 C15 H15C 109.5
H15A C15 H15C 109.5
H15B C15 H15C 109.5
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
Cl1 C2 1.732(2)
O1 N1 1.225(2)
O2 N1 1.214(3)
O3 C8 1.236(2)
O4 C11 1.355(2)
O4 H4 0.8200
O5 C15 1.390(3)
O5 H5 0.8200
N1 C5 1.477(3)
N2 C7 1.263(2)
N2 N3 1.376(2)
N3 C8 1.342(2)
N3 H3B 0.81(3)
C1 C6 1.397(3)
C1 C2 1.398(3)
C1 C7 1.466(3)
C2 C3 1.387(3)
C3 C4 1.358(4)
C3 H3 0.9300
C4 C5 1.378(3)
C4 H4A 0.9300
C5 C6 1.375(3)
C6 H6 0.9300
C7 H7 0.9300
C8 C9 1.481(2)
C9 C10 1.385(3)
C9 C14 1.389(3)
C10 C11 1.388(3)
C10 H10 0.9300
C11 C12 1.385(3)
C12 C13 1.372(3)
C12 H12 0.9300
C13 C14 1.379(3)
C13 H13 0.9300
C14 H14 0.9300
C15 H15A 0.9600
C15 H15B 0.9600
C15 H15C 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
O4 H4 O3 2_646 0.82 1.91 2.7237(19) 169.4
O4 H4 N2 2_646 0.82 2.62 3.118(2) 120.4
O5 H5 O3 2_646 0.82 2.00 2.817(2) 175.2
N3 H3B O5 . 0.81(3) 2.05(3) 2.854(2) 173(3)
