#------------------------------------------------------------------------------
#$Date: 2011-09-10 04:16:28 +0100 (Sat, 10 Sep 2011) $
#$Revision: 25271 $
#$URL: svn://www.crystallography.net/cod/cif/2/2006494.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_2006494
loop_
_publ_author_name
'Abboud, K. A.'
'Ortiz, C. G.'
'Palenik, R. C.'
'Palenik, G. J.'
_publ_section_title
;
 2-[1-(Salicyloylhydrazono)ethyl]pyridinium Chloride Dihydrate at 173K
;
_journal_issue                   9
_journal_name_full               'Acta Crystallographica Section C'
_journal_page_first              1322
_journal_page_last               1323
_journal_volume                  53
_journal_year                    1997
_chemical_formula_moiety         'C14 H14 Cl N3 O2,2(H2 O)'
_chemical_formula_sum            'C14 H18 Cl N3 O4'
_chemical_formula_weight         327.76
_chemical_name_systematic
;
 ?
;
_space_group_IT_number           2
_symmetry_cell_setting           triclinic
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_audit_creation_method           SHELXTL5
_cell_angle_alpha                99.0420(10)
_cell_angle_beta                 93.042(2)
_cell_angle_gamma                92.225(2)
_cell_formula_units_Z            2
_cell_length_a                   7.6381(2)
_cell_length_b                   8.08440(10)
_cell_length_c                   12.5955(4)
_cell_measurement_reflns_used    2788
_cell_measurement_temperature    173(2)
_cell_measurement_theta_max      26.34
_cell_measurement_theta_min      1.64
_cell_volume                     766.14(3)
_computing_cell_refinement       'SMART and SAINT (Siemens, 1995)'
_computing_data_collection       'SMART (Siemens, 1995)'
_computing_data_reduction        'SHELXTL5, (Sheldrick, 1995)'
_computing_molecular_graphics    SHELXTL5
_computing_publication_material  SHELXTL5
_computing_structure_refinement  SHELXTL5
_computing_structure_solution    SHELXTL5
_diffrn_ambient_temperature      173(2)
_diffrn_measurement_device       'SMART platform'
_diffrn_measurement_method       '\w scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'normal-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.032
_diffrn_reflns_av_sigmaI/netI    0.034
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            3874
_diffrn_reflns_theta_max         26.34
_diffrn_reflns_theta_min         1.64
_diffrn_standards_decay_%        '< 1'
_exptl_absorpt_coefficient_mu    0.27
_exptl_absorpt_correction_T_max  0.973
_exptl_absorpt_correction_T_min  0.848
_exptl_absorpt_correction_type   'empirical (SHELXTL5; Sheldrick, 1995)'
_exptl_crystal_colour            Colorless
_exptl_crystal_density_diffrn    1.421
_exptl_crystal_description       Needles
_exptl_crystal_F_000             344
_exptl_crystal_size_max          0.23
_exptl_crystal_size_mid          0.13
_exptl_crystal_size_min          0.10
_refine_diff_density_max         0.22
_refine_diff_density_min         -0.20
_refine_ls_extinction_coef       0.018(3)
_refine_ls_extinction_method     SHELXTL5
_refine_ls_goodness_of_fit_all   1.094
_refine_ls_goodness_of_fit_obs   1.092
_refine_ls_hydrogen_treatment    refall
_refine_ls_matrix_type           full
_refine_ls_number_parameters     272
_refine_ls_number_reflns         2646
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.230
_refine_ls_restrained_S_obs      1.092
_refine_ls_R_factor_all          0.043
_refine_ls_R_factor_obs          0.036
_refine_ls_shift/esd_max         0.000
_refine_ls_shift/esd_mean        0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w = 1/[\s^2^(Fo^2^)+(0.0398P)^2^+0.3882P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_all         0.108
_refine_ls_wR_factor_obs         0.090
_reflns_number_observed          2377
_reflns_number_total             2677
_reflns_observed_criterion       >2sigma(I)
_[local]_cod_data_source_file    fr1045.cif
_[local]_cod_data_source_block   1
_cod_database_code               2006494
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'
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
Cl1 0.0381(3) 0.0293(3) 0.0255(3) 0.0075(2) 0.0058(2) 0.0050(2)
O1 0.0500(9) 0.0235(7) 0.0257(7) 0.0063(6) 0.0109(6) 0.0071(6)
O2 0.0452(8) 0.0287(7) 0.0209(7) 0.0062(6) 0.0059(6) 0.0063(5)
O3 0.0434(8) 0.0259(7) 0.0244(8) 0.0051(6) 0.0065(7) 0.0073(6)
O4 0.0427(9) 0.0381(9) 0.0272(8) 0.0048(7) 0.0028(6) 0.0006(7)
N1 0.0230(7) 0.0192(7) 0.0228(8) 0.0005(6) 0.0005(6) 0.0022(6)
N2 0.0225(7) 0.0211(7) 0.0190(7) 0.0007(6) 0.0027(6) 0.0018(6)
N3 0.0264(8) 0.0225(8) 0.0191(8) 0.0027(6) 0.0056(6) 0.0051(6)
C1 0.0272(9) 0.0296(10) 0.0218(9) -0.0022(7) 0.0034(7) 0.0037(8)
C2 0.0275(10) 0.0356(11) 0.0241(10) 0.0002(8) 0.0045(8) -0.0037(8)
C3 0.0273(10) 0.0277(10) 0.0342(11) 0.0037(8) -0.0006(8) -0.0044(8)
C4 0.0268(9) 0.0214(9) 0.0294(10) 0.0035(7) -0.0014(7) 0.0041(8)
C5 0.0174(8) 0.0209(8) 0.0223(9) -0.0003(6) -0.0019(6) 0.0031(7)
C6 0.0202(8) 0.0209(9) 0.0236(9) -0.0010(7) -0.0009(7) 0.0047(7)
C6' 0.0424(12) 0.0274(11) 0.0268(10) 0.0046(9) 0.0039(9) 0.0099(8)
C7 0.0234(9) 0.0218(9) 0.0223(9) 0.0004(7) 0.0007(7) 0.0016(7)
C8 0.0198(8) 0.0252(9) 0.0203(9) -0.0009(7) 0.0013(7) -0.0003(7)
C9 0.0212(9) 0.0286(9) 0.0232(9) -0.0005(7) -0.0003(7) 0.0018(7)
C10 0.0258(9) 0.0433(11) 0.0203(9) 0.0011(8) 0.0020(7) 0.0029(8)
C11 0.0255(10) 0.0444(12) 0.0247(10) 0.0060(8) 0.0037(8) -0.0055(9)
C12 0.0285(10) 0.0306(11) 0.0353(11) 0.0046(8) 0.0023(8) -0.0042(9)
C13 0.0247(9) 0.0256(9) 0.0301(10) -0.0005(7) 0.0020(7) 0.0009(8)
loop_
_atom_site_label
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_thermal_displace_type
_atom_site_calc_flag
_atom_site_occupancy
_atom_site_type_symbol
Cl1 0.22297(6) 0.84988(6) 0.42511(4) 0.0306(2) Uani d 1 Cl
O1 0.1924(2) 1.2588(2) -0.02893(10) 0.0323(3) Uani d 1 O
O2 0.1263(2) 0.9702(2) 0.21545(11) 0.0311(3) Uani d 1 O
H2' 0.144(4) 0.940(4) 0.281(3) 0.073(9) Uiso d 1 H
O3 0.3634(2) 1.1750(2) -0.22474(13) 0.0307(3) Uani d 1 O
H3A 0.304(3) 1.187(3) -0.175(2) 0.039(7) Uiso d 1 H
H3B 0.307(4) 1.189(4) -0.281(3) 0.059(8) Uiso d 1 H
O4 0.1960(2) 1.2004(2) 0.58022(12) 0.0364(4) Uani d 1 O
H4A 0.215(4) 1.111(4) 0.541(3) 0.065(9) Uiso d 1 H
H4B 0.082(4) 1.201(4) 0.578(2) 0.063(9) Uiso d 1 H
N1 0.4495(2) 0.8505(2) -0.25027(12) 0.0219(3) Uani d 1 N
H1' 0.415(3) 0.958(3) -0.2312(19) 0.043(6) Uiso d 1 H
N2 0.3078(2) 0.9472(2) -0.06694(11) 0.0210(3) Uani d 1 N
N3 0.2338(2) 1.0083(2) 0.02669(12) 0.0223(3) Uani d 1 N
H3' 0.222(3) 0.952(3) 0.0784(19) 0.040(6) Uiso d 1 H
C1 0.5157(2) 0.8139(2) -0.34692(15) 0.0263(4) Uani d 1 C
H1 0.523(3) 0.902(3) -0.3844(18) 0.034(6) Uiso d 1 H
C2 0.5706(2) 0.6554(3) -0.3822(2) 0.0299(4) Uani d 1 C
H2 0.619(3) 0.632(3) -0.450(2) 0.041(6) Uiso d 1 H
C3 0.5532(2) 0.5345(2) -0.3162(2) 0.0307(4) Uani d 1 C
H3 0.596(3) 0.422(3) -0.3418(19) 0.047(7) Uiso d 1 H
C4 0.4822(2) 0.5752(2) -0.2168(2) 0.0259(4) Uani d 1 C
H4 0.469(3) 0.492(3) -0.1702(18) 0.038(6) Uiso d 1 H
C5 0.4295(2) 0.7363(2) -0.18302(14) 0.0204(4) Uani d 1 C
C6 0.3517(2) 0.7934(2) -0.07924(14) 0.0215(4) Uani d 1 C
C6' 0.3293(3) 0.6783(3) 0.0017(2) 0.0315(4) Uani d 1 C
H6'A 0.411(4) 0.708(4) 0.061(3) 0.070(9) Uiso d 1 H
H6'B 0.327(3) 0.565(4) -0.028(2) 0.052(7) Uiso d 1 H
H6'C 0.214(4) 0.687(3) 0.029(2) 0.052(7) Uiso d 1 H
C7 0.1783(2) 1.1686(2) 0.04036(14) 0.0227(4) Uani d 1 C
C8 0.1003(2) 1.2276(2) 0.14529(13) 0.0222(4) Uani d 1 C
C9 0.0756(2) 1.1319(2) 0.22763(14) 0.0247(4) Uani d 1 C
C10 -0.0016(2) 1.2027(3) 0.3215(2) 0.0300(4) Uani d 1 C
H10 -0.018(3) 1.136(3) 0.377(2) 0.044(6) Uiso d 1 H
C11 -0.0492(2) 1.3668(3) 0.3352(2) 0.0325(5) Uani d 1 C
H11 -0.101(3) 1.408(3) 0.401(2) 0.051(7) Uiso d 1 H
C12 -0.0236(3) 1.4640(3) 0.2551(2) 0.0324(4) Uani d 1 C
H12 -0.054(3) 1.577(3) 0.265(2) 0.047(7) Uiso d 1 H
C13 0.0487(2) 1.3939(2) 0.1611(2) 0.0272(4) Uani d 1 C
H13 0.064(3) 1.456(3) 0.1042(18) 0.034(6) Uiso d 1 H
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'
Cl Cl 0.1484 0.1585 '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
C9 O2 H2' 109.(2) ?
H3A O3 H3B 111.(3) ?
H4A O4 H4B 103.(3) ?
C1 N1 C5 123.0(2) ?
C1 N1 H1' 116.6(15) ?
C5 N1 H1' 120.4(15) ?
C6 N2 N3 117.20(10) yes
N2 N3 C7 118.8(2) yes
N2 N3 H3' 123.5(16) ?
C7 N3 H3' 117.7(16) ?
N1 C1 C2 120.5(2) ?
N1 C1 H1 114.5(14) ?
C2 C1 H1 125.0(14) ?
C1 C2 C3 118.6(2) ?
C1 C2 H2 119.5(14) ?
C3 C2 H2 121.9(14) ?
C2 C3 C4 119.8(2) ?
C2 C3 H3 117.6(14) ?
C4 C3 H3 122.6(14) ?
C5 C4 C3 120.3(2) ?
C5 C4 H4 119.0(14) ?
C3 C4 H4 120.7(13) ?
N1 C5 C4 117.8(2) ?
N1 C5 C6 117.24(15) ?
C4 C5 C6 125.0(2) ?
N2 C6 C5 113.9(2) yes
N2 C6 C6' 124.9(2) yes
C5 C6 C6' 121.2(2) yes
C6 C6' H6'A 111.0(18) ?
C6 C6' H6'B 113.5(16) ?
H6'A C6' H6'B 114.(2) ?
C6 C6' H6'C 110.2(15) ?
H6'A C6' H6'C 107.(2) ?
H6'B C6' H6'C 101.(2) ?
O1 C7 N3 122.1(2) yes
O1 C7 C8 122.1(2) yes
N3 C7 C8 115.8(2) yes
C13 C8 C9 118.3(2) ?
C13 C8 C7 116.0(2) ?
C9 C8 C7 125.8(2) ?
O2 C9 C10 120.5(2) ?
O2 C9 C8 119.8(2) ?
C10 C9 C8 119.7(2) ?
C11 C10 C9 120.7(2) ?
C11 C10 H10 120.4(14) ?
C9 C10 H10 118.9(14) ?
C10 C11 C12 120.3(2) ?
C10 C11 H11 116.8(16) ?
C12 C11 H11 122.9(16) ?
C13 C12 C11 119.4(2) ?
C13 C12 H12 119.9(15) ?
C11 C12 H12 120.7(15) ?
C12 C13 C8 121.6(2) ?
C12 C13 H13 121.1(13) ?
C8 C13 H13 117.3(13) ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_publ_flag
O1 C7 1.228(2) yes
O2 C9 1.366(2) ?
O2 H2' 0.90(3) ?
O3 H3A 0.79(3) ?
O3 H3B 0.83(3) ?
O4 H4A 0.83(3) ?
O4 H4B 0.87(3) ?
N1 C1 1.338(2) ?
N1 C5 1.357(2) ?
N1 H1' 0.92(2) ?
N2 C6 1.288(2) yes
N2 N3 1.365(2) yes
N3 C7 1.367(2) yes
N3 H3' 0.86(2) ?
C1 C2 1.378(3) ?
C1 H1 0.92(2) ?
C2 C3 1.386(3) ?
C2 H2 0.94(2) ?
C3 C4 1.388(3) ?
C3 H3 0.99(3) ?
C4 C5 1.388(2) ?
C4 H4 0.96(2) ?
C5 C6 1.479(2) yes
C6 C6' 1.496(3) yes
C6' H6'A 0.94(3) ?
C6' H6'B 0.93(3) ?
C6' H6'C 0.96(3) ?
C7 C8 1.496(2) yes
C8 C13 1.402(3) ?
C8 C9 1.405(3) ?
C9 C10 1.400(3) ?
C10 C11 1.376(3) ?
C10 H10 0.96(2) ?
C11 C12 1.390(3) ?
C11 H11 0.95(3) ?
C12 C13 1.382(3) ?
C12 H12 0.94(3) ?
C13 H13 0.95(2) ?