#------------------------------------------------------------------------------
#$Date: 2016-02-20 02:53:41 +0200 (Sat, 20 Feb 2016) $
#$Revision: 176768 $
#$URL: svn://www.crystallography.net/cod/cif/2/10/05/2100503.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_2100503
loop_
_publ_author_name
'Sharif, Shasad'
'Powell, Douglas R.'
'Schagen, David'
'Steiner, Thomas'
'Toney, Michael D.'
'Fogle, Emily'
'Limbach, Hans-Heinrich'
_publ_section_title
;
 X-ray crystallographic structures of enamine and amine Schiff bases of
 pyridoxal and its 1:1 hydrogen-bonded complexes with benzoic acid
 derivatives: evidence for coupled inter- and intramolecular proton
 transfer
;
_journal_coeditor_code           SN5027
_journal_issue                   3
_journal_name_full               'Acta Crystallographica Section B'
_journal_page_first              480
_journal_page_last               487
_journal_paper_doi               10.1107/S0108768105040590
_journal_volume                  62
_journal_year                    2006
_chemical_formula_moiety         'C15 H17 N2 O2, C7 H4 N O4'
_chemical_formula_sum            'C22 H21 N3 O6'
_chemical_formula_weight         423.42
_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'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                114.88(4)
_cell_angle_beta                 99.61(5)
_cell_angle_gamma                96.03(5)
_cell_formula_units_Z            2
_cell_length_a                   7.683(5)
_cell_length_b                   12.188(6)
_cell_length_c                   12.562(6)
_cell_measurement_reflns_used    25
_cell_measurement_temperature    295(2)
_cell_measurement_theta_max      15.0
_cell_measurement_theta_min      7.0
_cell_volume                     1031.8(11)
_computing_molecular_graphics    'SHELXTL (Sheldrick, 2000)'
_computing_publication_material  'SHELXTL (Sheldrick, 2000)'
_computing_structure_refinement  'SHELXTL (Sheldrick, 2000)'
_computing_structure_solution    'SHELXTL (Sheldrick, 2000)'
_diffrn_ambient_temperature      295(2)
_diffrn_measured_fraction_theta_full 0.992
_diffrn_measured_fraction_theta_max 0.992
_diffrn_measurement_device_type  'Stoe four-circle diffractometer'
_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  0.0176
_diffrn_reflns_av_sigmaI/netI    0.0299
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            3866
_diffrn_reflns_theta_full        25.00
_diffrn_reflns_theta_max         25.00
_diffrn_reflns_theta_min         2.74
_diffrn_standards_decay_%        3
_diffrn_standards_interval_time  30
_diffrn_standards_number         3
_exptl_absorpt_coefficient_mu    0.101
_exptl_absorpt_correction_T_max  0.990
_exptl_absorpt_correction_T_min  0.961
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.363
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             444
_exptl_crystal_size_max          0.40
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.10
_refine_diff_density_max         0.197
_refine_diff_density_min         -0.205
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.003
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     289
_refine_ls_number_reflns         3591
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.003
_refine_ls_R_factor_all          0.0837
_refine_ls_R_factor_gt           0.0493
_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)+(0.0780P)²+0.2500P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1268
_refine_ls_wR_factor_ref         0.1534
_reflns_number_gt                2383
_reflns_number_total             3591
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            sn5027.cif
_cod_data_source_block           compound_II_
_cod_original_cell_volume        1031.8(10)
_cod_database_code               2100503
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
N N1 0.3837(3) 0.39957(19) 0.61412(18) 0.0491(5) Uani d . 1
H H1 0.436(3) 0.490(3) 0.661(2) 0.059 Uiso d . 1
N N2 0.1882(3) -0.05211(18) 0.43292(19) 0.0543(5) Uani d . 1
C C2 0.4127(3) 0.3212(2) 0.6597(2) 0.0505(6) Uani d . 1
C C3 0.3362(3) 0.1967(2) 0.5884(2) 0.0508(6) Uani d . 1
C C4 0.2308(3) 0.1581(2) 0.4724(2) 0.0455(6) Uani d . 1
C C5 0.2015(3) 0.2461(2) 0.4302(2) 0.0448(6) Uani d . 1
C C6 0.2821(3) 0.3653(2) 0.5036(2) 0.0498(6) Uani d . 1
H H6 0.2665 0.4247 0.4766 0.060 Uiso calc R 1
C C2' 0.5234(4) 0.3678(2) 0.7851(2) 0.0652(8) Uani d . 1
H H2'A 0.5569 0.4560 0.8211 0.098 Uiso d R 1
H H2'B 0.6299 0.3329 0.7829 0.098 Uiso d R 1
H H2'C 0.4546 0.3444 0.8320 0.098 Uiso d R 1
O O3' 0.3704(3) 0.11905(18) 0.63546(17) 0.0718(6) Uani d . 1
H H3' 0.314(4) 0.040(3) 0.574(3) 0.086 Uiso d . 1
C C4' 0.1539(3) 0.0284(2) 0.3975(2) 0.0487(6) Uani d . 1
H H4' 0.0782 0.0037 0.3221 0.058 Uiso calc R 1
O O5' -0.0915(2) 0.15341(17) 0.29060(16) 0.0599(5) Uani d . 1
H H5' -0.161(4) 0.217(3) 0.313(3) 0.072 Uiso d . 1
C C5' 0.0863(3) 0.2116(2) 0.3073(2) 0.0539(6) Uani d . 1
H H5'A 0.0832 0.2855 0.2961 0.065 Uiso calc R 1
H H5'B 0.1404 0.1568 0.2463 0.065 Uiso calc R 1
C C1" -0.0151(4) -0.4320(2) 0.2301(3) 0.0601(7) Uani d . 1
C C2" 0.0859(4) -0.3819(3) 0.3470(3) 0.0668(8) Uani d . 1
H H2" 0.1094 -0.4331 0.3833 0.080 Uiso calc R 1
C C3" 0.1523(4) -0.2573(2) 0.4106(2) 0.0585(7) Uani d . 1
H H3" 0.2216 -0.2253 0.4891 0.070 Uiso calc R 1
C C4" 0.1175(3) -0.1796(2) 0.3598(2) 0.0500(6) Uani d . 1
C C5" 0.0193(4) -0.2286(2) 0.2422(3) 0.0660(8) Uani d . 1
H H5" -0.0025 -0.1776 0.2055 0.079 Uiso calc R 1
C C6" -0.0461(4) -0.3535(2) 0.1798(3) 0.0667(8) Uani d . 1
H H6" -0.1135 -0.3859 0.1008 0.080 Uiso calc R 1
C C1"' -0.0881(5) -0.5683(3) 0.1590(3) 0.0893(10) Uani d . 1
H H1"A -0.1705 -0.5843 0.0854 0.134 Uiso d R 1
H H1"B -0.1497 -0.5969 0.2058 0.134 Uiso d R 1
H H1"C 0.0095 -0.6108 0.1405 0.134 Uiso d R 1
O O1A 0.3064(2) 0.67846(15) 0.65137(16) 0.0641(5) Uani d . 1
O O2A 0.5470(2) 0.62426(15) 0.72514(16) 0.0579(5) Uani d . 1
O O3A 0.8271(4) 0.7693(2) 0.9965(3) 0.1141(10) Uani d . 1
O O4A 0.5413(4) 0.7212(2) 0.9720(2) 0.0875(7) Uani d . 1
N N1A 0.6726(4) 0.7791(2) 0.9651(2) 0.0654(6) Uani d . 1
C C1A 0.5391(3) 0.8338(2) 0.8060(2) 0.0418(5) Uani d . 1
C C2A 0.6496(3) 0.8689(2) 0.9179(2) 0.0467(6) Uani d . 1
C C3A 0.7410(3) 0.9875(2) 0.9901(2) 0.0600(7) Uani d . 1
H H3A 0.8153 1.0084 1.0650 0.072 Uiso calc R 1
C C4A 0.7209(4) 1.0747(2) 0.9496(3) 0.0670(8) Uani d . 1
H H4A 0.7822 1.1556 0.9976 0.080 Uiso calc R 1
C C5A 0.6120(4) 1.0443(2) 0.8398(3) 0.0602(7) Uani d . 1
H H5A 0.5995 1.1041 0.8130 0.072 Uiso calc R 1
C C6A 0.5209(3) 0.9252(2) 0.7690(2) 0.0493(6) Uani d . 1
H H6A 0.4454 0.9053 0.6948 0.059 Uiso calc R 1
C C7A 0.4535(3) 0.7015(2) 0.7206(2) 0.0447(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
C2 N1 C6 123.2(2) y
C2 N1 H1 122.1(14) ?
C6 N1 H1 114.8(14) ?
C4' N2 C4" 122.0(2) ?
N1 C2 C3 118.4(2) ?
N1 C2 C2' 119.7(2) ?
C3 C2 C2' 122.0(2) ?
O3' C3 C2 117.3(2) ?
O3' C3 C4 123.0(2) y
C2 C3 C4 119.8(2) ?
C3 C4 C5 119.2(2) ?
C3 C4 C4' 119.8(2) y
C5 C4 C4' 121.0(2) ?
C6 C5 C4 117.9(2) ?
C6 C5 C5' 119.9(2) y
C4 C5 C5' 122.2(2) ?
N1 C6 C5 121.6(2) ?
N1 C6 H6 119.2 ?
C5 C6 H6 119.2 ?
C2 C2' H2'A 109.5 ?
C2 C2' H2'B 109.5 ?
H2'A C2' H2'B 109.5 ?
C2 C2' H2'C 109.5 ?
H2'A C2' H2'C 109.5 ?
H2'B C2' H2'C 109.5 ?
C3 O3' H3' 105.3(19) ?
N2 C4' C4 121.1(2) y
N2 C4' H4' 119.4 ?
C4 C4' H4' 119.4 ?
C5' O5' H5' 107.0(17) ?
O5' C5' C5 112.9(2) y
O5' C5' H5'A 109.0 ?
C5 C5' H5'A 109.0 ?
O5' C5' H5'B 109.0 ?
C5 C5' H5'B 109.0 ?
H5'A C5' H5'B 107.8 ?
C6" C1" C2" 117.8(2) ?
C6" C1" C1"' 120.8(3) ?
C2" C1" C1"' 121.4(3) ?
C3" C2" C1" 120.8(3) ?
C3" C2" H2" 119.6 ?
C1" C2" H2" 119.6 ?
C4" C3" C2" 120.8(2) ?
C4" C3" H3" 119.6 ?
C2" C3" H3" 119.6 ?
C3" C4" C5" 119.1(2) ?
C3" C4" N2 116.9(2) ?
C5" C4" N2 124.0(2) ?
C6" C5" C4" 119.4(2) ?
C6" C5" H5" 120.3 ?
C4" C5" H5" 120.3 ?
C1" C6" C5" 122.2(3) ?
C1" C6" H6" 118.9 ?
C5" C6" H6" 118.9 ?
C1" C1"' H1"A 109.5 ?
C1" C1"' H1"B 109.5 ?
H1"A C1"' H1"B 109.5 ?
C1" C1"' H1"C 109.5 ?
H1"A C1"' H1"C 109.5 ?
H1"B C1"' H1"C 109.5 ?
O4A N1A O3A 124.4(3) ?
O4A N1A C2A 119.1(2) ?
O3A N1A C2A 116.5(3) ?
C2A C1A C6A 116.9(2) ?
C2A C1A C7A 122.9(2) ?
C6A C1A C7A 119.9(2) ?
C3A C2A C1A 122.6(2) ?
C3A C2A N1A 116.9(2) ?
C1A C2A N1A 120.5(2) ?
C4A C3A C2A 118.6(2) ?
C4A C3A H3A 120.7 ?
C2A C3A H3A 120.7 ?
C5A C4A C3A 120.7(2) ?
C5A C4A H4A 119.6 ?
C3A C4A H4A 119.6 ?
C4A C5A C6A 119.8(3) ?
C4A C5A H5A 120.1 ?
C6A C5A H5A 120.1 ?
C5A C6A C1A 121.3(2) ?
C5A C6A H6A 119.4 ?
C1A C6A H6A 119.4 ?
O1A C7A O2A 126.1(2) y
O1A C7A C1A 119.2(2) y
O2A C7A C1A 114.7(2) y
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_publ_flag
N1 C2 1.324(3) y
N1 C6 1.339(3) y
N1 H1 1.01(3) ?
N2 C4' 1.270(3) y
N2 C4" 1.417(3) ?
C2 C3 1.394(3) ?
C2 C2' 1.492(4) ?
C3 O3' 1.336(3) y
C3 C4 1.396(3) y
C4 C5 1.405(3) ?
C4 C4' 1.449(3) y
C5 C6 1.356(3) ?
C5 C5' 1.504(3) y
C6 H6 0.9300 ?
C2' H2'A 0.9600 ?
C2' H2'B 0.9600 ?
C2' H2'C 0.9600 ?
O3' H3' 0.95(3) ?
C4' H4' 0.9300 ?
O5' C5' 1.410(3) y
O5' H5' 0.96(3) ?
C5' H5'A 0.9700 ?
C5' H5'B 0.9700 ?
C1" C6" 1.369(4) ?
C1" C2" 1.378(4) ?
C1" C1"' 1.504(4) ?
C2" C3" 1.373(4) ?
C2" H2" 0.9300 ?
C3" C4" 1.372(3) ?
C3" H3" 0.9300 ?
C4" C5" 1.378(4) ?
C5" C6" 1.375(4) ?
C5" H5" 0.9300 ?
C6" H6" 0.9300 ?
C1"' H1"A 0.9600 ?
C1"' H1"B 0.9600 ?
C1"' H1"C 0.9600 ?
O1A C7A 1.230(3) y
O2A C7A 1.256(3) y
O3A N1A 1.221(3) ?
O4A N1A 1.206(3) ?
N1A C2A 1.460(3) ?
C1A C2A 1.378(3) ?
C1A C6A 1.387(3) ?
C1A C7A 1.507(3) y
C2A C3A 1.370(4) ?
C3A C4A 1.369(4) ?
C3A H3A 0.9300 ?
C4A C5A 1.364(4) ?
C4A H4A 0.9300 ?
C5A C6A 1.371(4) ?
C5A H5A 0.9300 ?
C6A H6A 0.9300 ?
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
N1 H1 O2A . 1.01(3) 1.55(3) 2.549(3) 170(2)
N1 H1 O1A . 1.01(3) 2.63(3) 3.362(3) 129.4(18)
O3' H3' N2 . 0.95(3) 1.69(3) 2.553(3) 150(3)
O5' H5' O1A 2_566 0.96(3) 1.75(3) 2.704(3) 175(3)
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
_geom_torsion_publ_flag
C6 N1 C2 C3 1.1(4) ?
C6 N1 C2 C2' -178.2(2) ?
N1 C2 C3 O3' 178.7(2) ?
C2' C2 C3 O3' -2.0(4) ?
N1 C2 C3 C4 -0.5(4) ?
C2' C2 C3 C4 178.7(2) ?
O3' C3 C4 C5 179.9(2) ?
C2 C3 C4 C5 -0.9(4) ?
O3' C3 C4 C4' -0.3(4) ?
C2 C3 C4 C4' 178.9(2) ?
C3 C4 C5 C6 1.8(4) ?
C4' C4 C5 C6 -178.0(2) ?
C3 C4 C5 C5' -178.7(2) ?
C4' C4 C5 C5' 1.5(4) ?
C2 N1 C6 C5 -0.1(4) ?
C4 C5 C6 N1 -1.4(4) ?
C5' C5 C6 N1 179.1(2) ?
C4" N2 C4' C4 -178.6(2) ?
C3 C4 C4' N2 -3.7(4) ?
C5 C4 C4' N2 176.1(2) ?
C6 C5 C5' O5' -122.0(3) y
C4 C5 C5' O5' 58.5(3) ?
C6" C1" C2" C3" 0.3(4) ?
C1"' C1" C2" C3" 179.7(3) ?
C1" C2" C3" C4" 0.9(5) ?
C2" C3" C4" C5" -2.0(4) ?
C2" C3" C4" N2 178.7(3) ?
C4' N2 C4" C3" -175.3(2) ?
C4' N2 C4" C5" 5.5(4) ?
C3" C4" C5" C6" 1.9(5) ?
N2 C4" C5" C6" -178.9(3) ?
C2" C1" C6" C5" -0.3(5) ?
C1"' C1" C6" C5" -179.8(3) ?
C4" C5" C6" C1" -0.8(5) ?
C6A C1A C2A C3A -1.1(4) ?
C7A C1A C2A C3A 173.4(2) ?
C6A C1A C2A N1A 178.4(2) ?
C7A C1A C2A N1A -7.1(4) ?
O4A N1A C2A C3A 124.2(3) ?
O3A N1A C2A C3A -55.0(3) ?
O4A N1A C2A C1A -55.4(4) ?
O3A N1A C2A C1A 125.4(3) ?
C1A C2A C3A C4A 0.4(4) ?
N1A C2A C3A C4A -179.1(2) ?
C2A C3A C4A C5A 0.0(4) ?
C3A C4A C5A C6A 0.2(4) ?
C4A C5A C6A C1A -1.0(4) ?
C2A C1A C6A C5A 1.4(4) ?
C7A C1A C6A C5A -173.3(2) ?
C2A C1A C7A O1A 149.2(2) ?
C6A C1A C7A O1A -36.5(3) y
C2A C1A C7A O2A -33.5(3) ?
C6A C1A C7A O2A 140.9(2) y
