#------------------------------------------------------------------------------
#$Date: 2008-02-04 17:24:24 +0000 (Mon, 04 Feb 2008) $
#$Revision: 87 $
#$URL: svn://www.crystallography.net/cod/cif/2/2204630.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_2204630
loop_
_publ_author_name
'Shao, Si-Chang'
'You, Zhong-Lu'
'Shao-Hua Fan'
'Tang, Lu-Lu'
'Xiong, Zhong-Duo'
'Zhu, Hai-Liang'
_publ_section_title
;
The Schiff base 2-nitrobenzaldehyde picoloylhydrazone
;
_journal_issue                   12
_journal_name_full               'Acta Crystallographica, Section E'
_journal_page_first              o2183
_journal_page_last               o2184
_journal_volume                  60
_journal_year                    2004
_chemical_formula_moiety         'C13 H10 N4 O3'
_chemical_formula_sum            'C13 H10 N4 O3'
_chemical_formula_weight         270.25
_chemical_name_common            '2-nitrobenzaldehyde picoloylhydrazone'
_chemical_name_systematic
;
2-nitrobenzaldehyde (pyridine-2-carbonyl)hydrazone
;
_symmetry_cell_setting           Monoclinic
_symmetry_space_group_name_Hall  '-C 2yc'
_symmetry_space_group_name_H-M   'C 2/c'
_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                 103.415(4)
_cell_angle_gamma                90.00
_cell_formula_units_Z            8
_cell_length_a                   12.191(3)
_cell_length_b                   9.398(3)
_cell_length_c                   21.624(6)
_cell_measurement_reflns_used    2674
_cell_measurement_temperature    298(2)
_cell_measurement_theta_max      27.906
_cell_measurement_theta_min      2.796
_cell_volume                     2410.0(11)
_computing_cell_refinement       SMART
_computing_data_collection       'SMART (Bruker, 1998)'
_computing_data_reduction        'SAINT (Bruker, 1998)'
_computing_molecular_graphics    'SHELXTL (Sheldrick, 1997b)'
_computing_publication_material  SHELXTL
_computing_structure_refinement  'SHELXL97 (Sheldrick, 1997a)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 1997a)'
_diffrn_ambient_temperature      298(2)
_diffrn_measured_fraction_theta_full 0.995
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measurement_device_type  'Bruker SMART CCD area-detector'
_diffrn_measurement_method       \w
_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  0.0253
_diffrn_reflns_av_sigmaI/netI    0.0277
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       27
_diffrn_reflns_limit_l_min       -25
_diffrn_reflns_number            6729
_diffrn_reflns_theta_full        26.49
_diffrn_reflns_theta_max         26.49
_diffrn_reflns_theta_min         1.94
_diffrn_standards_decay_%        0
_diffrn_standards_interval_count 0
_diffrn_standards_interval_time  0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.110
_exptl_absorpt_correction_T_max  0.9869
_exptl_absorpt_correction_T_min  0.9656
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SADABS; Sheldrick, 1996)'
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.490
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             1120
_exptl_crystal_size_max          0.32
_exptl_crystal_size_mid          0.30
_exptl_crystal_size_min          0.12
_refine_diff_density_max         0.187
_refine_diff_density_min         -0.241
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.053
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     184
_refine_ls_number_reflns         2486
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.053
_refine_ls_R_factor_all          0.0521
_refine_ls_R_factor_gt           0.0428
_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/[\s^2^(Fo^2^)+(0.0675P)^2^+0.5995P] where P = (Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1152
_refine_ls_wR_factor_ref         0.1219
_reflns_number_gt                2022
_reflns_number_total             2486
_reflns_threshold_expression     I>2\s(I)
_[local]_cod_original_file       cf6387.cif
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_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_
_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_type_symbol
O1 0.93152(11) 0.36164(16) 0.66863(6) 0.0699(4) Uani d . 1 O
O2 0.83084(10) 0.32420(14) 0.57457(6) 0.0626(4) Uani d . 1 O
O3 1.01588(9) -0.01070(15) 0.34731(6) 0.0685(4) Uani d . 1 O
N1 0.92060(11) 0.35238(14) 0.61157(6) 0.0451(3) Uani d . 1 N
N2 0.98282(10) 0.15256(13) 0.44585(6) 0.0399(3) Uani d . 1 N
N3 0.90419(10) 0.06170(14) 0.41154(6) 0.0405(3) Uani d D 1 N
N4 0.74431(10) -0.12126(14) 0.35758(6) 0.0426(3) Uani d . 1 N
C1 1.03322(11) 0.31882(14) 0.52948(6) 0.0344(3) Uani d . 1 C
C2 1.02018(11) 0.38007(15) 0.58607(6) 0.0360(3) Uani d . 1 C
C3 1.10072(13) 0.46868(16) 0.62262(7) 0.0446(4) Uani d . 1 C
H3 1.0897 0.5068 0.6604 0.053 Uiso calc R 1 H
C4 1.19692(13) 0.49964(18) 0.60255(8) 0.0485(4) Uani d . 1 C
H4 1.2512 0.5596 0.6265 0.058 Uiso calc R 1 H
C5 1.21267(13) 0.44179(18) 0.54691(8) 0.0474(4) Uani d . 1 C
H5 1.2779 0.4625 0.5334 0.057 Uiso calc R 1 H
C6 1.13259(12) 0.35343(16) 0.51108(7) 0.0406(4) Uani d . 1 C
H6 1.1449 0.3156 0.4735 0.049 Uiso calc R 1 H
C7 0.95429(12) 0.21782(16) 0.49070(7) 0.0403(3) Uani d . 1 C
H7 0.8839 0.2020 0.4991 0.048 Uiso calc R 1 H
C8 0.92673(11) -0.01454(15) 0.36308(7) 0.0379(3) Uani d . 1 C
C9 0.83031(11) -0.10468(14) 0.32920(6) 0.0342(3) Uani d . 1 C
C10 0.83383(13) -0.16666(16) 0.27209(7) 0.0424(4) Uani d . 1 C
H10 0.8948 -0.1516 0.2538 0.051 Uiso calc R 1 H
C11 0.74506(13) -0.25142(18) 0.24258(7) 0.0480(4) Uani d . 1 C
H11 0.7447 -0.2942 0.2038 0.058 Uiso calc R 1 H
C12 0.65747(13) -0.27182(19) 0.27120(8) 0.0509(4) Uani d . 1 C
H12 0.5970 -0.3298 0.2525 0.061 Uiso calc R 1 H
C13 0.66041(13) -0.20481(19) 0.32821(8) 0.0517(4) Uani d . 1 C
H13 0.6002 -0.2188 0.3472 0.062 Uiso calc R 1 H
H3A 0.8359(10) 0.054(2) 0.4192(9) 0.080 Uiso d D 1 H
loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_12
_atom_site_aniso_U_13
_atom_site_aniso_U_23
O1 0.0717(9) 0.0943(11) 0.0525(7) 0.0031(8) 0.0327(6) 0.0051(7)
O2 0.0396(6) 0.0772(9) 0.0759(8) -0.0103(6) 0.0232(6) -0.0209(7)
O3 0.0417(7) 0.0848(10) 0.0857(9) -0.0189(6) 0.0287(6) -0.0402(7)
N1 0.0438(7) 0.0444(7) 0.0516(8) 0.0012(6) 0.0201(6) -0.0012(6)
N2 0.0342(6) 0.0406(7) 0.0439(7) -0.0036(5) 0.0070(5) -0.0063(5)
N3 0.0326(6) 0.0451(7) 0.0437(7) -0.0060(5) 0.0084(5) -0.0087(5)
N4 0.0398(7) 0.0460(7) 0.0450(7) -0.0061(6) 0.0163(5) -0.0076(6)
C1 0.0317(7) 0.0336(7) 0.0371(7) 0.0012(6) 0.0066(6) 0.0023(5)
C2 0.0339(7) 0.0361(7) 0.0392(7) 0.0025(6) 0.0108(6) 0.0032(6)
C3 0.0478(9) 0.0436(8) 0.0415(8) 0.0004(7) 0.0086(7) -0.0064(6)
C4 0.0421(8) 0.0468(9) 0.0534(9) -0.0105(7) 0.0044(7) -0.0076(7)
C5 0.0357(8) 0.0514(10) 0.0568(9) -0.0072(7) 0.0143(7) 0.0009(7)
C6 0.0384(8) 0.0438(8) 0.0419(8) -0.0013(6) 0.0138(6) -0.0016(6)
C7 0.0340(7) 0.0455(8) 0.0420(8) -0.0036(6) 0.0099(6) -0.0036(6)
C8 0.0322(7) 0.0391(8) 0.0424(7) 0.0006(6) 0.0089(6) -0.0022(6)
C9 0.0320(7) 0.0334(7) 0.0371(7) 0.0015(6) 0.0079(5) 0.0016(5)
C10 0.0387(8) 0.0488(9) 0.0426(8) -0.0035(7) 0.0152(6) -0.0041(6)
C11 0.0471(8) 0.0557(10) 0.0412(8) -0.0042(7) 0.0100(7) -0.0129(7)
C12 0.0378(8) 0.0561(10) 0.0581(10) -0.0108(8) 0.0095(7) -0.0167(8)
C13 0.0399(8) 0.0604(10) 0.0598(10) -0.0118(8) 0.0214(7) -0.0136(8)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
O1 N1 1.213(2)
O2 N1 1.225(2)
O3 C8 1.213(2)
N1 C2 1.468(2)
N2 C7 1.263(2)
N2 N3 1.367(2)
N3 C8 1.349(2)
N3 H3A 0.889(9)
N4 C13 1.329(2)
N4 C9 1.341(2)
C1 C2 1.395(2)
C1 C6 1.398(2)
C1 C7 1.468(2)
C2 C3 1.386(2)
C3 C4 1.373(2)
C3 H3 0.9300
C4 C5 1.374(2)
C4 H4 0.9300
C5 C6 1.376(2)
C5 H5 0.9300
C6 H6 0.9300
C7 H7 0.9300
C8 C9 1.496(2)
C9 C10 1.375(2)
C10 C11 1.376(2)
C10 H10 0.9300
C11 C12 1.366(2)
C11 H11 0.9300
C12 C13 1.377(2)
C12 H12 0.9300
C13 H13 0.9300
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
O1 N1 O2 123.38(13)
O1 N1 C2 117.64(13)
O2 N1 C2 118.96(12)
C7 N2 N3 115.91(12)
C8 N3 N2 120.65(12)
C8 N3 H3A 118.1(14)
N2 N3 H3A 121.2(14)
C13 N4 C9 116.55(12)
C2 C1 C6 115.87(13)
C2 C1 C7 125.10(13)
C6 C1 C7 118.96(13)
C3 C2 C1 122.57(13)
C3 C2 N1 115.50(13)
C1 C2 N1 121.93(12)
C4 C3 C2 119.42(14)
C4 C3 H3 120.3
C2 C3 H3 120.3
C3 C4 C5 119.75(14)
C3 C4 H4 120.1
C5 C4 H4 120.1
C4 C5 C6 120.47(14)
C4 C5 H5 119.8
C6 C5 H5 119.8
C5 C6 C1 121.92(14)
C5 C6 H6 119.0
C1 C6 H6 119.0
N2 C7 C1 119.46(13)
N2 C7 H7 120.3
C1 C7 H7 120.3
O3 C8 N3 124.04(13)
O3 C8 C9 122.20(13)
N3 C8 C9 113.75(12)
N4 C9 C10 123.52(13)
N4 C9 C8 116.78(12)
C10 C9 C8 119.69(12)
C9 C10 C11 118.47(13)
C9 C10 H10 120.8
C11 C10 H10 120.8
C12 C11 C10 118.99(14)
C12 C11 H11 120.5
C10 C11 H11 120.5
C11 C12 C13 118.71(15)
C11 C12 H12 120.6
C13 C12 H12 120.6
N4 C13 C12 123.74(14)
N4 C13 H13 118.1
C12 C13 H13 118.1
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
N3 H3A O2 7_656 0.889(9) 2.363(15) 3.1384(18) 145.8(19)