#------------------------------------------------------------------------------
#$Date: 2016-02-20 18:35:30 +0200 (Sat, 20 Feb 2016) $
#$Revision: 176787 $
#$URL: svn://www.crystallography.net/cod/cif/2/21/06/2210689.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_2210689
loop_
_publ_author_name
'Zhu, Li-Na'
'Li, Chang-Qing'
'Li, Xiao-Zeng'
'Li, Rong'
_publ_section_title
;
 Bis(2-hydroxy-1-naphthaldehyde) oxaloyldihydrazone dihydrate
;
_journal_issue                   10
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o4603
_journal_page_last               o4605
_journal_paper_doi               10.1107/S1600536806037615
_journal_volume                  62
_journal_year                    2006
_chemical_formula_iupac          'C24 H18 N4 O4 , 2H2 O'
_chemical_formula_moiety         'C24 H18 N4 O4 , 2H2 O'
_chemical_formula_sum            'C24 H22 N4 O6'
_chemical_formula_weight         462.46
_chemical_name_systematic
;
Bis(2-hydroxy-1-naphthaldehyde) oxaloyldihydrazone dihydrate
;
_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
_cell_angle_alpha                90.00
_cell_angle_beta                 114.983(5)
_cell_angle_gamma                90.00
_cell_formula_units_Z            2
_cell_length_a                   13.678(4)
_cell_length_b                   5.9250(18)
_cell_length_c                   14.883(5)
_cell_measurement_reflns_used    649
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      26.30
_cell_measurement_theta_min      2.76
_cell_volume                     1093.3(6)
_computing_cell_refinement       'SAINT (Bruker, 2003)'
_computing_data_collection       'APEXII (Bruker, 2003)'
_computing_data_reduction        SAINT
_computing_molecular_graphics    'SHELXTL (Bruker, 2003)'
_computing_publication_material  SHELXTL
_computing_structure_refinement  'SHELXL97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 1997)'
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device_type  'Bruker APEX-II CCD area-detector'
_diffrn_measurement_method       'φ and 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  0.0381
_diffrn_reflns_av_sigmaI/netI    0.0501
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_k_min       -3
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            5069
_diffrn_reflns_theta_full        25.00
_diffrn_reflns_theta_max         25.00
_diffrn_reflns_theta_min         1.64
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.103
_exptl_absorpt_correction_T_max  1.000000
_exptl_absorpt_correction_T_min  0.822124
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SADABS; Sheldrick, 1996)'
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.405
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       needle
_exptl_crystal_F_000             484
_exptl_crystal_size_max          0.20
_exptl_crystal_size_mid          0.18
_exptl_crystal_size_min          0.10
_refine_diff_density_max         0.298
_refine_diff_density_min         -0.249
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.020
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     155
_refine_ls_number_reflns         1918
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.020
_refine_ls_R_factor_all          0.1017
_refine_ls_R_factor_gt           0.0527
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.001
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0569P)²+0.2643P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1155
_refine_ls_wR_factor_ref         0.1353
_reflns_number_gt                1149
_reflns_number_total             1918
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            kp2043.cif
_cod_data_source_block           I
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               2210689
_cod_database_fobs_code          2210689
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
N N1 0.12945(16) 0.4243(3) 0.04378(15) 0.0398(6) Uani d . 1
N N2 0.07885(16) 0.2389(3) 0.06101(15) 0.0405(6) Uani d . 1
H H2 0.0823 0.2123 0.1191 0.049 Uiso calc R 1
O O1 0.17894(17) 0.6733(4) -0.07084(13) 0.0592(6) Uani d . 1
H H1 0.1481 0.5705 -0.0563 0.089 Uiso calc R 1
O O2 0.01142(15) 0.1287(3) -0.10093(14) 0.0513(5) Uani d . 1
O O3 0.1155(2) 0.2429(5) 0.27006(17) 0.1025(9) Uani d . 1
H H3WA 0.0685 0.3549 0.2426 0.154 Uiso d R 1
H H3WB 0.0975 0.1741 0.3114 0.154 Uiso d R 1
C C1 0.2356(2) 0.7980(4) 0.01065(19) 0.0416(7) Uani d . 1
C C2 0.2877(2) 0.9913(5) -0.0042(2) 0.0518(8) Uani d . 1
H H2A 0.2825 1.0247 -0.0671 0.062 Uiso calc R 1
C C3 0.3451(2) 1.1276(5) 0.0731(2) 0.0507(8) Uani d . 1
H H3 0.3791 1.2536 0.0621 0.061 Uiso calc R 1
C C4 0.3551(2) 1.0850(4) 0.1701(2) 0.0403(7) Uani d . 1
C C5 0.4141(2) 1.2294(5) 0.2501(2) 0.0512(8) Uani d . 1
H H5 0.4462 1.3579 0.2387 0.061 Uiso calc R 1
C C6 0.4251(2) 1.1857(5) 0.3428(2) 0.0603(9) Uani d . 1
H H6 0.4646 1.2828 0.3946 0.072 Uiso calc R 1
C C7 0.3767(2) 0.9928(6) 0.3605(2) 0.0613(9) Uani d . 1
H H7 0.3848 0.9614 0.4245 0.074 Uiso calc R 1
C C8 0.3175(2) 0.8499(5) 0.28468(19) 0.0501(8) Uani d . 1
H H8 0.2855 0.7238 0.2981 0.060 Uiso calc R 1
C C9 0.30387(19) 0.8895(4) 0.18657(18) 0.0367(6) Uani d . 1
C C10 0.24212(19) 0.7450(4) 0.10432(18) 0.0352(6) Uani d . 1
C C11 0.18548(19) 0.5491(4) 0.11817(19) 0.0389(6) Uani d . 1
H H11 0.1900 0.5147 0.1808 0.047 Uiso calc R 1
C C12 0.02400(19) 0.1008(4) -0.0154(2) 0.0382(6) Uani 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'
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_publ_flag
C11 N1 N2 117.6(2) yes
C12 N2 N1 118.2(2) yes
C12 N2 H2 120.9 ?
N1 N2 H2 120.9 ?
C1 O1 H1 109.5 ?
H3WA O3 H3WB 108.2 ?
O1 C1 C10 123.0(2) ?
O1 C1 C2 116.0(2) ?
C10 C1 C2 120.9(2) ?
C3 C2 C1 120.0(3) ?
C3 C2 H2A 120.0 ?
C1 C2 H2A 120.0 ?
C2 C3 C4 122.2(3) ?
C2 C3 H3 118.9 ?
C4 C3 H3 118.9 ?
C5 C4 C3 121.9(3) ?
C5 C4 C9 119.6(3) ?
C3 C4 C9 118.5(2) ?
C6 C5 C4 121.6(3) ?
C6 C5 H5 119.2 ?
C4 C5 H5 119.2 ?
C5 C6 C7 119.4(3) ?
C5 C6 H6 120.3 ?
C7 C6 H6 120.3 ?
C8 C7 C6 120.8(3) ?
C8 C7 H7 119.6 ?
C6 C7 H7 119.6 ?
C7 C8 C9 121.6(3) ?
C7 C8 H8 119.2 ?
C9 C8 H8 119.2 ?
C8 C9 C4 116.9(2) ?
C8 C9 C10 123.7(2) ?
C4 C9 C10 119.4(2) ?
C1 C10 C9 118.9(2) ?
C1 C10 C11 120.5(2) ?
C9 C10 C11 120.6(2) ?
N1 C11 C10 119.8(2) yes
N1 C11 H11 120.1 ?
C10 C11 H11 120.1 ?
O2 C12 N2 125.6(2) yes
O2 C12 C12 122.1(3) yes
N2 C12 C12 112.3(3) yes
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 C11 . 1.282(3) yes
N1 N2 . 1.379(3) yes
N2 C12 . 1.344(3) yes
N2 H2 . 0.8600 ?
O1 C1 . 1.350(3) yes
O1 H1 . 0.8200 ?
O2 C12 . 1.221(3) yes
O3 H3WA . 0.8940 ?
O3 H3WB . 0.8556 ?
C1 C10 . 1.394(4) ?
C1 C2 . 1.415(4) ?
C2 C3 . 1.352(4) ?
C2 H2A . 0.9300 ?
C3 C4 . 1.413(4) ?
C3 H3 . 0.9300 ?
C4 C5 . 1.411(4) ?
C4 C9 . 1.427(3) ?
C5 C6 . 1.348(4) ?
C5 H5 . 0.9300 ?
C6 C7 . 1.401(4) ?
C6 H6 . 0.9300 ?
C7 C8 . 1.368(4) ?
C7 H7 . 0.9300 ?
C8 C9 . 1.411(4) ?
C8 H8 . 0.9300 ?
C9 C10 . 1.439(3) ?
C10 C11 . 1.458(3) yes
C11 H11 . 0.9300 ?
C12 C12 3 1.525(5) yes
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
_geom_hbond_publ_flag
N2 H2 O3 1_555 0.86 2.10 2.935(9) 162.4 yes
O1 H1 N1 1_555 0.82 1.83 2.554(9) 146.0 yes
O3 H3WB O2 4_566 0.86 2.40 2.933(9) 121.0 yes
loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion_site_symmetry_4
_geom_torsion
C11 N1 N2 C12 . -177.0(2)
O1 C1 C2 C3 . 179.1(3)
C10 C1 C2 C3 . 0.1(4)
C1 C2 C3 C4 . -0.3(4)
C2 C3 C4 C5 . -179.3(3)
C2 C3 C4 C9 . 0.8(4)
C3 C4 C5 C6 . -178.7(3)
C9 C4 C5 C6 . 1.1(4)
C4 C5 C6 C7 . -0.2(4)
C5 C6 C7 C8 . -0.7(5)
C6 C7 C8 C9 . 0.6(5)
C7 C8 C9 C4 . 0.3(4)
C7 C8 C9 C10 . -179.7(3)
C5 C4 C9 C8 . -1.1(4)
C3 C4 C9 C8 . 178.7(2)
C5 C4 C9 C10 . 178.9(2)
C3 C4 C9 C10 . -1.2(3)
O1 C1 C10 C9 . -179.5(2)
C2 C1 C10 C9 . -0.6(4)
O1 C1 C10 C11 . -0.7(4)
C2 C1 C10 C11 . 178.2(2)
C8 C9 C10 C1 . -178.8(2)
C4 C9 C10 C1 . 1.1(3)
C8 C9 C10 C11 . 2.4(4)
C4 C9 C10 C11 . -177.6(2)
N2 N1 C11 C10 . 179.0(2)
C1 C10 C11 N1 . 0.1(4)
C9 C10 C11 N1 . 178.9(2)
N1 N2 C12 O2 . -2.7(4)
N1 N2 C12 C12 3 177.9(2)
