#------------------------------------------------------------------------------
#$Date: 2016-02-21 02:03:34 +0200 (Sun, 21 Feb 2016) $
#$Revision: 176798 $
#$URL: svn://www.crystallography.net/cod/cif/2/23/61/2236158.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_2236158
loop_
_publ_author_name
'Zhang, Xiyue'
'Fu, Xiaobo'
'Tan, Langzhu'
'Wang, Chaixia'
'Fan, Weixing'
_publ_section_title
;
 4-Dimethylamino-N'-(4-nitrobenzylidene)benzohydrazide methanol
 monosolvate
;
_journal_coeditor_code           CV5333
_journal_issue                   10
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o2828
_journal_paper_doi               10.1107/S1600536812037063
_journal_volume                  68
_journal_year                    2012
_chemical_formula_iupac          'C16 H16 N4 O3, C H4 O'
_chemical_formula_moiety         'C16 H16 N4 O3, C H4 O'
_chemical_formula_sum            'C17 H20 N4 O4'
_chemical_formula_weight         344.37
_chemical_name_systematic
;
4-Dimethylamino-N'-(4-nitrobenzylidene)benzohydrazide methanol
monosolvate
;
_space_group_IT_number           2
_symmetry_cell_setting           triclinic
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                72.279(2)
_cell_angle_beta                 83.444(2)
_cell_angle_gamma                73.984(2)
_cell_formula_units_Z            2
_cell_length_a                   6.6621(12)
_cell_length_b                   10.6685(17)
_cell_length_c                   13.3437(13)
_cell_measurement_reflns_used    2473
_cell_measurement_temperature    298(2)
_cell_measurement_theta_max      26.5
_cell_measurement_theta_min      2.5
_cell_volume                     867.9(2)
_computing_cell_refinement       'SAINT (Bruker, 1998)'
_computing_data_collection       'SMART (Bruker, 1998)'
_computing_data_reduction        'SAINT (Bruker, 1998)'
_computing_molecular_graphics    'SHELXTL (Sheldrick, 2008)'
_computing_publication_material  'SHELXTL (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      298(2)
_diffrn_measured_fraction_theta_full 0.974
_diffrn_measured_fraction_theta_max 0.974
_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  0.0345
_diffrn_reflns_av_sigmaI/netI    0.0406
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            6198
_diffrn_reflns_theta_full        25.50
_diffrn_reflns_theta_max         25.50
_diffrn_reflns_theta_min         1.60
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.096
_exptl_absorpt_correction_T_max  0.9783
_exptl_absorpt_correction_T_min  0.9718
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SADABS; Sheldrick, 1996)'
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.318
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             364
_exptl_crystal_size_max          0.30
_exptl_crystal_size_mid          0.27
_exptl_crystal_size_min          0.23
_refine_diff_density_max         0.318
_refine_diff_density_min         -0.396
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.076
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     233
_refine_ls_number_reflns         3140
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.076
_refine_ls_R_factor_all          0.0859
_refine_ls_R_factor_gt           0.0575
_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)+(0.1182P)²+0.1132P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1643
_refine_ls_wR_factor_ref         0.2083
_reflns_number_gt                2082
_reflns_number_total             3140
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            cv5333.cif
_cod_data_source_block           I
_cod_database_code               2236158
_cod_database_fobs_code          2236158
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -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
_atom_site_symmetry_multiplicity
N N1 0.0844(3) 0.62271(17) 0.39221(13) 0.0471(5) Uani d . 1 1
N N2 0.0240(3) 0.56468(18) 0.32624(14) 0.0478(5) Uani d D 1 1
N N3 0.1415(4) 0.9440(2) 0.71802(16) 0.0655(6) Uani d . 1 1
N N4 -0.0400(4) 0.2426(2) -0.00213(16) 0.0715(6) Uani d . 1 1
O O1 0.3228(3) 0.9304(2) 0.7318(2) 0.1055(8) Uani d . 1 1
O O2 -0.0001(4) 1.0126(2) 0.75895(17) 0.0929(7) Uani d . 1 1
O O3 0.3593(2) 0.47225(17) 0.29021(14) 0.0672(5) Uani d . 1 1
O O4 0.5727(2) 0.63544(19) 0.33104(18) 0.0796(6) Uani d . 1 1
H H4 0.4999 0.5874 0.3254 0.119 Uiso calc R 1 1
C C1 -0.0040(3) 0.7521(2) 0.51346(15) 0.0427(5) Uani d . 1 1
C C2 0.2010(3) 0.7245(2) 0.54349(16) 0.0484(5) Uani d . 1 1
H H2A 0.3067 0.6636 0.5177 0.058 Uiso calc R 1 1
C C3 0.2480(3) 0.7863(2) 0.61062(17) 0.0516(6) Uani d . 1 1
H H3 0.3848 0.7679 0.6307 0.062 Uiso calc R 1 1
C C4 0.0892(3) 0.8763(2) 0.64797(16) 0.0481(5) Uani d . 1 1
C C5 -0.1143(3) 0.9036(2) 0.62214(17) 0.0520(6) Uani d . 1 1
H H5 -0.2194 0.9628 0.6498 0.062 Uiso calc R 1 1
C C6 -0.1598(3) 0.8413(2) 0.55424(17) 0.0508(5) Uani d . 1 1
H H6 -0.2973 0.8594 0.5354 0.061 Uiso calc R 1 1
C C7 -0.0577(3) 0.6877(2) 0.44223(17) 0.0486(5) Uani d . 1 1
H H7 -0.1971 0.6943 0.4334 0.058 Uiso calc R 1 1
C C8 0.1735(3) 0.4890(2) 0.27631(17) 0.0458(5) Uani d . 1 1
C C9 0.1067(3) 0.4274(2) 0.20565(16) 0.0436(5) Uani d . 1 1
C C10 0.2582(3) 0.3367(2) 0.16454(18) 0.0561(6) Uani d . 1 1
H H10 0.3963 0.3175 0.1828 0.067 Uiso calc R 1 1
C C11 0.2113(4) 0.2743(3) 0.09784(19) 0.0611(6) Uani d . 1 1
H H11 0.3172 0.2125 0.0730 0.073 Uiso calc R 1 1
C C12 0.0067(4) 0.3021(2) 0.06654(17) 0.0537(6) Uani d . 1 1
C C13 -0.1459(3) 0.3920(2) 0.10855(17) 0.0547(6) Uani d . 1 1
H H13 -0.2842 0.4112 0.0904 0.066 Uiso calc R 1 1
C C14 -0.0978(3) 0.4533(2) 0.17627(17) 0.0495(5) Uani d . 1 1
H H14 -0.2038 0.5131 0.2029 0.059 Uiso calc R 1 1
C C15 -0.2519(5) 0.2624(4) -0.0273(2) 0.0884(9) Uani d . 1 1
H H15A -0.3265 0.2215 0.0343 0.133 Uiso calc R 1 1
H H15B -0.2541 0.2210 -0.0816 0.133 Uiso calc R 1 1
H H15C -0.3171 0.3581 -0.0515 0.133 Uiso calc R 1 1
C C16 0.1216(6) 0.1550(4) -0.0473(3) 0.1070(12) Uani d . 1 1
H H16A 0.2272 0.2015 -0.0802 0.161 Uiso calc R 1 1
H H16B 0.0640 0.1302 -0.0991 0.161 Uiso calc R 1 1
H H16C 0.1825 0.0745 0.0068 0.161 Uiso calc R 1 1
C C17 0.4766(4) 0.7717(3) 0.2827(2) 0.0819(8) Uani d . 1 1
H H17A 0.3486 0.7993 0.3205 0.123 Uiso calc R 1 1
H H17B 0.4468 0.7823 0.2114 0.123 Uiso calc R 1 1
H H17C 0.5681 0.8271 0.2830 0.123 Uiso calc R 1 1
H H2 -0.1140(17) 0.579(3) 0.324(2) 0.080 Uiso d 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'
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
C7 N1 N2 117.48(17)
C8 N2 N1 118.39(17)
C8 N2 H2 126.9(17)
N1 N2 H2 114.6(17)
O1 N3 O2 122.8(2)
O1 N3 C4 118.8(2)
O2 N3 C4 118.4(2)
C12 N4 C16 120.4(2)
C12 N4 C15 121.0(2)
C16 N4 C15 118.5(2)
C17 O4 H4 109.5
C6 C1 C2 118.84(19)
C6 C1 C7 119.61(19)
C2 C1 C7 121.54(18)
C3 C2 C1 120.56(19)
C3 C2 H2A 119.7
C1 C2 H2A 119.7
C2 C3 C4 118.83(19)
C2 C3 H3 120.6
C4 C3 H3 120.6
C5 C4 C3 122.28(19)
C5 C4 N3 119.25(19)
C3 C4 N3 118.5(2)
C4 C5 C6 118.42(19)
C4 C5 H5 120.8
C6 C5 H5 120.8
C5 C6 C1 121.0(2)
C5 C6 H6 119.5
C1 C6 H6 119.5
N1 C7 C1 120.24(19)
N1 C7 H7 119.9
C1 C7 H7 119.9
O3 C8 N2 120.71(18)
O3 C8 C9 121.40(18)
N2 C8 C9 117.89(17)
C10 C9 C14 117.15(18)
C10 C9 C8 117.77(18)
C14 C9 C8 125.07(18)
C11 C10 C9 122.1(2)
C11 C10 H10 119.0
C9 C10 H10 119.0
C10 C11 C12 120.9(2)
C10 C11 H11 119.5
C12 C11 H11 119.5
N4 C12 C13 121.8(2)
N4 C12 C11 121.1(2)
C13 C12 C11 117.08(19)
C14 C13 C12 121.61(19)
C14 C13 H13 119.2
C12 C13 H13 119.2
C13 C14 C9 121.15(19)
C13 C14 H14 119.4
C9 C14 H14 119.4
N4 C15 H15A 109.5
N4 C15 H15B 109.5
H15A C15 H15B 109.5
N4 C15 H15C 109.5
H15A C15 H15C 109.5
H15B C15 H15C 109.5
N4 C16 H16A 109.5
N4 C16 H16B 109.5
H16A C16 H16B 109.5
N4 C16 H16C 109.5
H16A C16 H16C 109.5
H16B C16 H16C 109.5
O4 C17 H17A 109.5
O4 C17 H17B 109.5
H17A C17 H17B 109.5
O4 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
N1 C7 1.264(3)
N1 N2 1.368(2)
N2 C8 1.349(3)
N2 H2 0.892(10)
N3 O1 1.205(3)
N3 O2 1.212(3)
N3 C4 1.464(3)
N4 C12 1.367(3)
N4 C16 1.427(4)
N4 C15 1.432(3)
O3 C8 1.228(2)
O4 C17 1.396(3)
O4 H4 0.8200
C1 C6 1.386(3)
C1 C2 1.394(3)
C1 C7 1.454(3)
C2 C3 1.368(3)
C2 H2A 0.9300
C3 C4 1.378(3)
C3 H3 0.9300
C4 C5 1.367(3)
C5 C6 1.376(3)
C5 H5 0.9300
C6 H6 0.9300
C7 H7 0.9300
C8 C9 1.468(3)
C9 C10 1.383(3)
C9 C14 1.390(3)
C10 C11 1.368(3)
C10 H10 0.9300
C11 C12 1.398(3)
C11 H11 0.9300
C12 C13 1.388(3)
C13 C14 1.374(3)
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
O4 H4 O3 . 0.82 1.92 2.733(2) 169.8
N2 H2 O4 1_455 0.892(10) 2.006(11) 2.889(2) 170(2)
