#------------------------------------------------------------------------------
#$Date: 2017-10-13 12:31:46 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201979 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/23/08/2230866.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_2230866
loop_
_publ_author_name
'Su, Fu'
'Gu, Zheng-Gui'
'Lin, Jun'
_publ_section_title
;
 N'-(4-Diethylamino-2-hydroxybenzylidene)-4-(dimethylamino)benzohydrazide
 methanol monosolvate
;
_journal_coeditor_code           SJ5154
_journal_issue                   7
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o1634
_journal_paper_doi               10.1107/S1600536811019957
_journal_volume                  67
_journal_year                    2011
_chemical_formula_iupac          'C20 H26 N4 O2, C H4 O'
_chemical_formula_moiety         'C20 H26 N4 O2, C H4 O'
_chemical_formula_sum            'C21 H30 N4 O3'
_chemical_formula_weight         386.49
_chemical_name_systematic
;
N'-(4-Diethylamino-2-hydroxybenzylidene)-4-(dimethylamino)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                111.511(3)
_cell_angle_beta                 92.811(2)
_cell_angle_gamma                96.492(2)
_cell_formula_units_Z            2
_cell_length_a                   6.786(3)
_cell_length_b                   11.791(3)
_cell_length_c                   14.252(2)
_cell_measurement_reflns_used    765
_cell_measurement_temperature    298(2)
_cell_measurement_theta_max      24.5
_cell_measurement_theta_min      2.6
_cell_volume                     1049.1(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 0.965
_diffrn_measured_fraction_theta_max 0.965
_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  0.0447
_diffrn_reflns_av_sigmaI/netI    0.0967
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            7543
_diffrn_reflns_theta_full        27.00
_diffrn_reflns_theta_max         27.00
_diffrn_reflns_theta_min         2.84
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.083
_exptl_absorpt_correction_T_max  0.9828
_exptl_absorpt_correction_T_min  0.9779
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SADABS; Bruker, 2001)'
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.224
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             416
_exptl_crystal_size_max          0.27
_exptl_crystal_size_mid          0.23
_exptl_crystal_size_min          0.21
_refine_diff_density_max         0.300
_refine_diff_density_min         -0.206
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.996
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     263
_refine_ls_number_reflns         4421
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      0.996
_refine_ls_R_factor_all          0.1753
_refine_ls_R_factor_gt           0.0701
_refine_ls_shift/su_max_lt       0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0676P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1410
_refine_ls_wR_factor_ref         0.1885
_reflns_number_gt                1809
_reflns_number_total             4421
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            sj5154.cif
_cod_data_source_block           I
_cod_database_code               2230866
_cod_database_fobs_code          2230866
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
_atom_site_disorder_assembly
_atom_site_disorder_group
O O1 -0.1048(3) 0.5092(2) 0.2045(2) 0.0741(8) Uani d . 1 1 . .
H H1 -0.0686 0.4564 0.2235 0.111 Uiso calc R 1 1 . .
O O2 -0.0566(3) 0.2247(2) 0.3184(2) 0.0770(8) Uani d . 1 1 . .
O O3 0.6751(4) 0.3787(2) 0.3427(2) 0.0907(9) Uani d . 1 1 . .
H H3 0.7586 0.3321 0.3371 0.136 Uiso calc R 1 1 . .
N N1 0.1680(4) 0.3808(2) 0.2520(2) 0.0549(7) Uani d . 1 1 . .
N N2 0.2452(4) 0.2985(2) 0.2885(2) 0.0564(8) Uani d D 1 1 . .
N N3 0.4202(4) -0.1790(2) 0.3829(2) 0.0632(8) Uani d . 1 1 . .
N N4 0.1131(4) 0.7762(2) 0.0366(2) 0.0705(9) Uani d . 1 1 . .
C C1 0.2398(4) 0.5230(2) 0.1692(2) 0.0488(8) Uani d . 1 1 . .
C C2 0.0478(5) 0.5553(3) 0.1644(2) 0.0487(8) Uani d . 1 1 . .
C C3 0.0066(4) 0.6387(3) 0.1211(2) 0.0535(9) Uani d . 1 1 . .
H H3A -0.1218 0.6588 0.1194 0.064 Uiso calc R 1 1 . .
C C4 0.1541(5) 0.6933(3) 0.0801(2) 0.0525(8) Uani d . 1 1 . .
C C5 0.3450(5) 0.6589(3) 0.0828(3) 0.0649(10) Uani d . 1 1 . .
H H5 0.4457 0.6922 0.0546 0.078 Uiso calc R 1 1 . .
C C6 0.3848(5) 0.5769(3) 0.1263(3) 0.0594(9) Uani d . 1 1 . .
H H6 0.5130 0.5564 0.1273 0.071 Uiso calc R 1 1 . .
C C7 0.2927(5) 0.4383(3) 0.2145(2) 0.0523(8) Uani d . 1 1 . .
H H7 0.4248 0.4246 0.2168 0.063 Uiso calc R 1 1 . .
C C8 0.1245(5) 0.2195(3) 0.3155(2) 0.0522(8) Uani d . 1 1 . .
C C9 0.2154(4) 0.1219(3) 0.3371(2) 0.0470(8) Uani d . 1 1 . .
C C10 0.0978(5) 0.0474(3) 0.3749(3) 0.0573(9) Uani d . 1 1 . .
H H10 -0.0301 0.0644 0.3897 0.069 Uiso calc R 1 1 . .
C C11 0.1637(5) -0.0504(3) 0.3910(2) 0.0596(9) Uani d . 1 1 . .
H H11 0.0806 -0.0973 0.4173 0.071 Uiso calc R 1 1 . .
C C12 0.3538(5) -0.0806(3) 0.3687(2) 0.0505(8) Uani d . 1 1 . .
C C13 0.4723(4) -0.0056(3) 0.3301(2) 0.0575(9) Uani d . 1 1 . .
H H13 0.6001 -0.0224 0.3148 0.069 Uiso calc R 1 1 . .
C C14 0.4036(5) 0.0927(3) 0.3145(2) 0.0553(9) Uani d . 1 1 . .
H H14 0.4855 0.1402 0.2883 0.066 Uiso calc R 1 1 . .
C C15 0.2976(6) -0.2536(3) 0.4256(3) 0.0780(11) Uani d . 1 1 . .
H H15A 0.2808 -0.2051 0.4946 0.117 Uiso calc R 1 1 . .
H H15B 0.3614 -0.3231 0.4233 0.117 Uiso calc R 1 1 . .
H H15C 0.1696 -0.2821 0.3869 0.117 Uiso calc R 1 1 . .
C C16 0.6191(5) -0.2071(3) 0.3638(3) 0.0789(12) Uani d . 1 1 . .
H H16A 0.6412 -0.2160 0.2956 0.118 Uiso calc R 1 1 . .
H H16B 0.6347 -0.2824 0.3728 0.118 Uiso calc R 1 1 . .
H H16C 0.7139 -0.1414 0.4103 0.118 Uiso calc R 1 1 . .
C C17 0.2791(6) 0.8609(3) 0.0203(3) 0.0792(12) Uani d . 1 1 . .
H H17A 0.2346 0.9396 0.0307 0.095 Uiso calc R 1 1 . .
H H17B 0.3917 0.8751 0.0698 0.095 Uiso calc R 1 1 . .
C C18 0.3427(6) 0.8094(4) -0.0821(3) 0.1027(14) Uani d . 1 1 . .
H H18A 0.3853 0.7310 -0.0929 0.154 Uiso calc R 1 1 . .
H H18B 0.4511 0.8645 -0.0893 0.154 Uiso calc R 1 1 . .
H H18C 0.2332 0.7989 -0.1312 0.154 Uiso calc R 1 1 . .
C C19 -0.0856(5) 0.8062(3) 0.0254(3) 0.0603(9) Uani d . 1 1 . .
H H19A -0.1818 0.7332 0.0115 0.072 Uiso calc R 1 1 . .
H H19B -0.0975 0.8310 -0.0322 0.072 Uiso calc R 1 1 . .
C C20 -0.1341(6) 0.9075(3) 0.1181(3) 0.0841(12) Uani d . 1 1 . .
H H20A -0.1327 0.8810 0.1742 0.126 Uiso calc R 1 1 . .
H H20B -0.2638 0.9272 0.1057 0.126 Uiso calc R 1 1 . .
H H20C -0.0366 0.9791 0.1336 0.126 Uiso calc R 1 1 . .
C C21 0.7364(6) 0.4885(4) 0.4255(3) 0.0977(14) Uani d . 1 1 . .
H H21A 0.8506 0.5328 0.4108 0.146 Uiso calc R 1 1 . .
H H21B 0.7706 0.4704 0.4841 0.146 Uiso calc R 1 1 . .
H H21C 0.6301 0.5378 0.4384 0.146 Uiso calc R 1 1 . .
H H2 0.3791(16) 0.309(3) 0.290(3) 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_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle
_geom_angle_publ_flag
C2 O1 H1 . . 109.5 ?
C21 O3 H3 . . 109.5 ?
C7 N1 N2 . . 115.4(3) ?
C8 N2 N1 . . 121.0(3) ?
C8 N2 H2 . . 129(2) ?
N1 N2 H2 . . 110(2) ?
C12 N3 C16 . . 121.6(3) ?
C12 N3 C15 . . 121.0(3) ?
C16 N3 C15 . . 117.3(3) ?
C4 N4 C19 . . 122.5(3) ?
C4 N4 C17 . . 120.5(3) ?
C19 N4 C17 . . 115.6(2) ?
C6 C1 C2 . . 116.7(3) ?
C6 C1 C7 . . 119.4(3) ?
C2 C1 C7 . . 123.9(3) ?
O1 C2 C3 . . 116.9(3) ?
O1 C2 C1 . . 121.8(3) ?
C3 C2 C1 . . 121.3(3) ?
C2 C3 C4 . . 121.2(3) ?
C2 C3 H3A . . 119.4 ?
C4 C3 H3A . . 119.4 ?
N4 C4 C3 . . 121.3(3) ?
N4 C4 C5 . . 121.2(3) ?
C3 C4 C5 . . 117.5(3) ?
C6 C5 C4 . . 120.9(3) ?
C6 C5 H5 . . 119.6 ?
C4 C5 H5 . . 119.6 ?
C5 C6 C1 . . 122.4(3) ?
C5 C6 H6 . . 118.8 ?
C1 C6 H6 . . 118.8 ?
N1 C7 C1 . . 123.7(3) ?
N1 C7 H7 . . 118.2 ?
C1 C7 H7 . . 118.2 ?
O2 C8 N2 . . 121.6(3) ?
O2 C8 C9 . . 121.1(3) ?
N2 C8 C9 . . 117.2(3) ?
C14 C9 C10 . . 117.2(3) ?
C14 C9 C8 . . 124.7(3) ?
C10 C9 C8 . . 117.9(3) ?
C11 C10 C9 . . 122.3(3) ?
C11 C10 H10 . . 118.8 ?
C9 C10 H10 . . 118.8 ?
C10 C11 C12 . . 121.0(3) ?
C10 C11 H11 . . 119.5 ?
C12 C11 H11 . . 119.5 ?
N3 C12 C11 . . 121.6(3) ?
N3 C12 C13 . . 121.7(3) ?
C11 C12 C13 . . 116.7(3) ?
C14 C13 C12 . . 121.6(3) ?
C14 C13 H13 . . 119.2 ?
C12 C13 H13 . . 119.2 ?
C9 C14 C13 . . 121.3(3) ?
C9 C14 H14 . . 119.4 ?
C13 C14 H14 . . 119.4 ?
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 ?
C18 C17 N4 . . 111.6(3) ?
C18 C17 H17A . . 109.3 ?
N4 C17 H17A . . 109.3 ?
C18 C17 H17B . . 109.3 ?
N4 C17 H17B . . 109.3 ?
H17A C17 H17B . . 108.0 ?
C17 C18 H18A . . 109.5 ?
C17 C18 H18B . . 109.5 ?
H18A C18 H18B . . 109.5 ?
C17 C18 H18C . . 109.5 ?
H18A C18 H18C . . 109.5 ?
H18B C18 H18C . . 109.5 ?
N4 C19 C20 . . 112.6(3) ?
N4 C19 H19A . . 109.1 ?
C20 C19 H19A . . 109.1 ?
N4 C19 H19B . . 109.1 ?
C20 C19 H19B . . 109.1 ?
H19A C19 H19B . . 107.8 ?
C19 C20 H20A . . 109.5 ?
C19 C20 H20B . . 109.5 ?
H20A C20 H20B . . 109.5 ?
C19 C20 H20C . . 109.5 ?
H20A C20 H20C . . 109.5 ?
H20B C20 H20C . . 109.5 ?
O3 C21 H21A . . 109.5 ?
O3 C21 H21B . . 109.5 ?
H21A C21 H21B . . 109.5 ?
O3 C21 H21C . . 109.5 ?
H21A C21 H21C . . 109.5 ?
H21B C21 H21C . . 109.5 ?
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
O1 C2 . 1.362(3) ?
O1 H1 . 0.8200 ?
O2 C8 . 1.239(3) ?
O3 C21 . 1.397(4) ?
O3 H3 . 0.8200 ?
N1 C7 . 1.281(4) ?
N1 N2 . 1.396(3) ?
N2 C8 . 1.344(4) ?
N2 H2 . 0.900(10) ?
N3 C12 . 1.368(3) ?
N3 C16 . 1.441(4) ?
N3 C15 . 1.454(4) ?
N4 C4 . 1.381(4) ?
N4 C19 . 1.448(4) ?
N4 C17 . 1.504(4) ?
C1 C6 . 1.396(4) ?
C1 C2 . 1.403(4) ?
C1 C7 . 1.441(4) ?
C2 C3 . 1.384(4) ?
C3 C4 . 1.395(4) ?
C3 H3A . 0.9300 ?
C4 C5 . 1.404(4) ?
C5 C6 . 1.369(4) ?
C5 H5 . 0.9300 ?
C6 H6 . 0.9300 ?
C7 H7 . 0.9300 ?
C8 C9 . 1.484(4) ?
C9 C14 . 1.382(4) ?
C9 C10 . 1.389(4) ?
C10 C11 . 1.373(4) ?
C10 H10 . 0.9300 ?
C11 C12 . 1.397(4) ?
C11 H11 . 0.9300 ?
C12 C13 . 1.404(4) ?
C13 C14 . 1.383(4) ?
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 C18 . 1.469(5) ?
C17 H17A . 0.9700 ?
C17 H17B . 0.9700 ?
C18 H18A . 0.9600 ?
C18 H18B . 0.9600 ?
C18 H18C . 0.9600 ?
C19 C20 . 1.501(5) ?
C19 H19A . 0.9700 ?
C19 H19B . 0.9700 ?
C20 H20A . 0.9600 ?
C20 H20B . 0.9600 ?
C20 H20C . 0.9600 ?
C21 H21A . 0.9600 ?
C21 H21B . 0.9600 ?
C21 H21C . 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 . 0.900(10) 2.073(15) 2.936(4) 160(3)
O3 H3 O2 1_655 0.82 1.84 2.661(3) 177
O1 H1 N1 . 0.82 2.02 2.727(3) 145
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 30656799
