#------------------------------------------------------------------------------
#$Date: 2016-02-14 05:40:26 +0100 (dom 14 de feb de 2016) $
#$Revision: 176432 $
#$URL: svn://www.crystallography.net/cod/cif/2/22/79/2227955.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/
#
# All data on this site have been placed in the public domain by the
# contributors.
#
data_2227955
loop_
_publ_author_name
'Wang, Yong'
'Sun, Yan Liang'
_publ_section_title
;
 N²,N^2'^-Bis[4-(dimethylamino)benzylidene]pyridine-2,6-dicarbohydrazide
 monohydrate
;
_journal_coeditor_code           RZ2479
_journal_issue                   11
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o2718
_journal_paper_doi               10.1107/S1600536810038778
_journal_volume                  66
_journal_year                    2010
_chemical_formula_iupac          'C25 H27 N7 O2, H2 O'
_chemical_formula_moiety         'C25 H27 N7 O2, H2 O'
_chemical_formula_sum            'C25 H29 N7 O3'
_chemical_formula_weight         475.54
_chemical_name_systematic
;
N²,N^2'^-Bis[4-(dimethylamino)benzylidene]pyridine-2,6-
dicarbohydrazide monohydrate
;
_space_group_IT_number           15
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-C 2yc'
_symmetry_space_group_name_H-M   'C 1 2/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                 97.8650(10)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   8.5718(11)
_cell_length_b                   10.2802(14)
_cell_length_c                   27.112(3)
_cell_measurement_reflns_used    1533
_cell_measurement_temperature    298(2)
_cell_measurement_theta_max      24.433
_cell_measurement_theta_min      3.034
_cell_volume                     2366.6(5)
_computing_cell_refinement       'SAINT (Siemens, 1996)'
_computing_data_collection       'SMART (Siemens, 1996)'
_computing_data_reduction        'SAINT (Siemens, 1996)'
_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 1.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_device_type  'Bruker SMART APEX  CCD area-detector'
_diffrn_measurement_method       'phi and omega 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  0.0391
_diffrn_reflns_av_sigmaI/netI    0.0456
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -32
_diffrn_reflns_number            5774
_diffrn_reflns_theta_full        25.01
_diffrn_reflns_theta_max         25.01
_diffrn_reflns_theta_min         1.52
_exptl_absorpt_coefficient_mu    0.091
_exptl_absorpt_correction_T_max  0.986
_exptl_absorpt_correction_T_min  0.968
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SADABS; Sheldrick, 1996)'
_exptl_crystal_colour            red
_exptl_crystal_density_diffrn    1.332
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             1008
_exptl_crystal_size_max          0.36
_exptl_crystal_size_mid          0.31
_exptl_crystal_size_min          0.16
_refine_diff_density_max         0.168
_refine_diff_density_min         -0.589
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.049
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     163
_refine_ls_number_reflns         2076
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.049
_refine_ls_R_factor_all          0.0948
_refine_ls_R_factor_gt           0.0621
_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)+(0.1275P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1866
_refine_ls_wR_factor_ref         0.2039
_reflns_number_gt                1348
_reflns_number_total             2076
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            rz2479.cif
_cod_data_source_block           I
_cod_original_cell_volume        2366.7(5)
_cod_original_sg_symbol_Hall     '-C 2yc  '
_cod_original_sg_symbol_H-M      'C 2/c  '
_cod_database_code               2227955
_cod_database_fobs_code          2227955
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y, -z+1/2'
'x+1/2, y+1/2, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y, z-1/2'
'-x+1/2, -y+1/2, -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_disorder_assembly
_atom_site_disorder_group
N N1 0.0000 0.0318(3) 0.2500 0.0419(8) Uani d S 1 . .
N N2 0.1517(3) 0.1645(2) 0.18533(9) 0.0456(6) Uani d . 1 . .
H H2A 0.0721 0.1938 0.1981 0.068 Uiso calc R 1 . .
N N3 0.2319(3) 0.2465(2) 0.15743(8) 0.0448(7) Uani d . 1 . .
N N4 0.4368(3) 0.7693(2) 0.05148(10) 0.0556(7) Uani d . 1 . .
O O1 0.3055(3) -0.0104(2) 0.17635(9) 0.0669(7) Uani d . 1 . .
O O2 1.0000 0.3442(4) 0.2500 0.0927(13) Uani d SD 1 . .
H H2 0.934(4) 0.398(3) 0.2352(16) 0.111 Uiso d D 1 . .
C C1 0.1949(3) 0.0402(3) 0.19306(10) 0.0445(7) Uani d . 1 . .
C C2 0.0935(3) -0.0351(3) 0.22381(10) 0.0411(7) Uani d . 1 . .
C C3 0.0976(3) -0.1702(3) 0.22298(11) 0.0488(8) Uani d . 1 . .
H H3 0.1650 -0.2141 0.2046 0.059 Uiso calc R 1 . .
C C4 0.0000 -0.2371(4) 0.2500 0.0535(11) Uani d S 1 . .
H H4 0.0000 -0.3276 0.2500 0.064 Uiso calc SR 1 . .
C C5 0.1730(3) 0.3604(3) 0.15200(10) 0.0462(7) Uani d . 1 . .
H H5 0.0817 0.3786 0.1657 0.055 Uiso calc R 1 . .
C C6 0.2429(3) 0.4630(3) 0.12527(10) 0.0424(7) Uani d . 1 . .
C C7 0.3772(3) 0.4455(3) 0.10227(11) 0.0452(7) Uani d . 1 . .
H H7 0.4255 0.3643 0.1035 0.054 Uiso calc R 1 . .
C C8 0.4387(3) 0.5447(3) 0.07816(11) 0.0474(8) Uani d . 1 . .
H H8 0.5276 0.5292 0.0628 0.057 Uiso calc R 1 . .
C C9 0.3728(3) 0.6699(3) 0.07561(10) 0.0420(7) Uani d . 1 . .
C C10 0.2390(3) 0.6870(3) 0.09890(11) 0.0494(8) Uani d . 1 . .
H H10 0.1917 0.7685 0.0982 0.059 Uiso calc R 1 . .
C C11 0.1755(3) 0.5864(3) 0.12276(11) 0.0489(8) Uani d . 1 . .
H H11 0.0854 0.6010 0.1376 0.059 Uiso calc R 1 . .
C C12 0.5716(4) 0.7484(3) 0.02620(13) 0.0685(10) Uani d . 1 . .
H H12A 0.6567 0.7141 0.0492 0.103 Uiso calc R 1 . .
H H12B 0.6031 0.8295 0.0130 0.103 Uiso calc R 1 . .
H H12C 0.5450 0.6877 -0.0005 0.103 Uiso calc R 1 . .
C C13 0.3639(4) 0.8964(3) 0.04783(13) 0.0639(9) Uani d . 1 . .
H H13A 0.2669 0.8923 0.0255 0.096 Uiso calc R 1 . .
H H13B 0.4335 0.9576 0.0354 0.096 Uiso calc R 1 . .
H H13C 0.3430 0.9235 0.0802 0.096 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'
O O 0.0106 0.0060 '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'
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 N1 C2 . 2 117.8(3) ?
C1 N2 N3 . . 121.5(2) ?
C1 N2 H2A . . 119.3 ?
N3 N2 H2A . . 119.3 ?
C5 N3 N2 . . 114.0(2) ?
C9 N4 C12 . . 121.2(3) ?
C9 N4 C13 . . 120.6(2) ?
C12 N4 C13 . . 118.0(2) ?
O1 C1 N2 . . 124.1(3) ?
O1 C1 C2 . . 121.7(3) ?
N2 C1 C2 . . 114.3(2) ?
N1 C2 C3 . . 122.9(3) ?
N1 C2 C1 . . 117.8(2) ?
C3 C2 C1 . . 119.3(2) ?
C4 C3 C2 . . 118.3(3) ?
C4 C3 H3 . . 120.8 ?
C2 C3 H3 . . 120.8 ?
C3 C4 C3 . 2 119.8(4) ?
C3 C4 H4 . . 120.1 ?
C3 C4 H4 2 . 120.1 ?
N3 C5 C6 . . 122.7(3) ?
N3 C5 H5 . . 118.7 ?
C6 C5 H5 . . 118.7 ?
C11 C6 C7 . . 117.3(2) ?
C11 C6 C5 . . 119.2(2) ?
C7 C6 C5 . . 123.4(3) ?
C8 C7 C6 . . 121.2(3) ?
C8 C7 H7 . . 119.4 ?
C6 C7 H7 . . 119.4 ?
C7 C8 C9 . . 122.2(3) ?
C7 C8 H8 . . 118.9 ?
C9 C8 H8 . . 118.9 ?
N4 C9 C10 . . 122.1(3) ?
N4 C9 C8 . . 121.5(2) ?
C10 C9 C8 . . 116.3(2) ?
C11 C10 C9 . . 121.6(3) ?
C11 C10 H10 . . 119.2 ?
C9 C10 H10 . . 119.2 ?
C10 C11 C6 . . 121.4(3) ?
C10 C11 H11 . . 119.3 ?
C6 C11 H11 . . 119.3 ?
N4 C12 H12A . . 109.5 ?
N4 C12 H12B . . 109.5 ?
H12A C12 H12B . . 109.5 ?
N4 C12 H12C . . 109.5 ?
H12A C12 H12C . . 109.5 ?
H12B C12 H12C . . 109.5 ?
N4 C13 H13A . . 109.5 ?
N4 C13 H13B . . 109.5 ?
H13A C13 H13B . . 109.5 ?
N4 C13 H13C . . 109.5 ?
H13A C13 H13C . . 109.5 ?
H13B C13 H13C . . 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
N1 C2 . 1.333(3) ?
N1 C2 2 1.333(3) ?
N2 C1 . 1.339(3) ?
N2 N3 . 1.378(3) ?
N2 H2A . 0.8600 ?
N3 C5 . 1.276(3) ?
N4 C9 . 1.368(3) ?
N4 C12 . 1.438(4) ?
N4 C13 . 1.446(4) ?
O1 C1 . 1.222(3) ?
O2 H2 . 0.85(3) ?
C1 C2 . 1.499(4) ?
C2 C3 . 1.390(4) ?
C3 C4 . 1.370(3) ?
C3 H3 . 0.9300 ?
C4 C3 2 1.370(3) ?
C4 H4 . 0.9300 ?
C5 C6 . 1.455(4) ?
C5 H5 . 0.9300 ?
C6 C11 . 1.392(4) ?
C6 C7 . 1.394(4) ?
C7 C8 . 1.356(4) ?
C7 H7 . 0.9300 ?
C8 C9 . 1.404(4) ?
C8 H8 . 0.9300 ?
C9 C10 . 1.394(4) ?
C10 C11 . 1.371(4) ?
C10 H10 . 0.9300 ?
C11 H11 . 0.9300 ?
C12 H12A . 0.9600 ?
C12 H12B . 0.9600 ?
C12 H12C . 0.9600 ?
C13 H13A . 0.9600 ?
C13 H13B . 0.9600 ?
C13 H13C . 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 H2A O2 1_455 0.86 2.23 2.967(4) 143
O2 H2 O1 3 0.85(3) 2.04(4) 2.844(3) 157(3)
