##############################################################################
###                                                                        ###
###        Electronic paper (Acta Crystallographica Section E)             ###
###                                                                        ###
##############################################################################
#                                                                            #
# This CIF contains the data in a paper accepted for publication in Acta     #
# Crystallographica Section E. It conforms to the requirements of Notes      #
# for Authors for Section E, and has been peer reviewed under the auspices   #
# of the IUCr Commission on Journals.                                        #
#                                                                            #
# Full details of the Crystallographic Information File format               #
# are given in the paper "The Crystallographic Information File (CIF):       #
# a New Standard Archive File for Crystallography" by S. R. Hall, F. H.      #
# Allen and I. D. Brown [Acta Cryst. (1991), A47, 655-685].                  #
#                                                                            #
# The current version of the core CIF dictionary is obtainable from          #
# ftp://ftp.iucr.org/pub/cif_core.dic. The current version number is 2.4.    #
#                                                                            #
# Software is freely available for graphical display of the structure(s) in  #
# this CIF.  For information consult the CIF home page http://www.iucr.org/  #
# cif/home.html                                                              #
#                                                                            #
# This file may be used for bona fide research purposes within the           #
# scientific community so long as proper attribution is given to the journal # 
# article from which it was obtained.                                        #
#                                                                            #
##############################################################################
                                             
data_I
_audit_creation_method     SHELXL-97
_chemical_name_systematic
;
rac-N-[Hydroxy(4-pyridyl)methyl]picolinamide
;
_chemical_name_common     ?
_chemical_formula_moiety     'C12 H11 N3 O2'
_chemical_formula_sum     'C12 H11 N3 O2'
_chemical_formula_iupac     'C12 H11 N3 O2'
_chemical_formula_weight     229.24
_chemical_melting_point     ?
_symmetry_cell_setting     monoclinic
_symmetry_space_group_name_H-M     'P 21/c'
_symmetry_space_group_name_Hall     '-P 2ybc'
loop_
    _symmetry_equiv_pos_site_id
    _symmetry_equiv_pos_as_xyz
    1 x,y,z
    2 -x,1/2+y,1/2-z
    3 -x,-y,-z
    4 x,1/2-y,1/2+z
_cell_length_a     12.1450(13)
_cell_length_b     5.6044(4)
_cell_length_c     16.3940(19)
_cell_angle_alpha     90.00
_cell_angle_beta     111.354(9)
_cell_angle_gamma     90.00
_cell_volume     1039.26(18)
_cell_formula_units_Z     4
_cell_measurement_reflns_used     10944
_cell_measurement_theta_min     1.81
_cell_measurement_theta_max     29.60
_cell_measurement_temperature     173(2)
_exptl_crystal_description     plate
_exptl_crystal_colour     colourless
_exptl_crystal_size_max     0.50
_exptl_crystal_size_mid     0.41
_exptl_crystal_size_min     0.10
_exptl_crystal_density_diffrn     1.465
_exptl_crystal_density_meas     ?
_exptl_crystal_density_method     'not measured'
_exptl_crystal_F_000     480
_exptl_absorpt_coefficient_mu     0.103
_exptl_absorpt_correction_type     none
_exptl_absorpt_process_details     ?
_exptl_absorpt_correction_T_min     ?
_exptl_absorpt_correction_T_max     ?
_exptl_special_details
;
;
_diffrn_ambient_temperature     173(2)
_diffrn_radiation_type     MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_source     'fine-focus sealed tube'
_diffrn_radiation_monochromator     graphite
_diffrn_measurement_device_type     'Stoe IPDS-2'
_diffrn_measurement_method     'phi + omega rotation'
_diffrn_detector_area_resol_mean     ?
_diffrn_reflns_number     14414
_diffrn_reflns_av_R_equivalents     0.0794
_diffrn_reflns_av_sigmaI/netI     0.0453
_diffrn_reflns_theta_min     1.80
_diffrn_reflns_theta_max     29.29
_diffrn_reflns_theta_full     29.29
_diffrn_measured_fraction_theta_max     0.992
_diffrn_measured_fraction_theta_full     0.992
_diffrn_reflns_limit_h_min     -16
_diffrn_reflns_limit_h_max     16
_diffrn_reflns_limit_k_min     -7
_diffrn_reflns_limit_k_max     7
_diffrn_reflns_limit_l_min     -22
_diffrn_reflns_limit_l_max     22
_diffrn_standards_number     0
_diffrn_standards_interval_count     ?
_diffrn_standards_interval_time     ?
_diffrn_standards_decay_%     0
_refine_special_details
;
Refinement of F² against ALL reflections. The weighted R-factor
wR and goodness of fit S are based on F², conventional
R-factors R are based on F, with F set to zero for
negative F². The threshold expression of F² >
σ(F²) is used only for calculating R-factors(gt) etc.
and is not relevant to the choice of reflections for refinement.
R-factors based on F² are statistically about twice as large
as those based on F, and R- factors based on ALL data will be
even larger.
;
_reflns_number_total     2823
_reflns_number_gt     2196
_reflns_threshold_expression     I>2σ(I)
_refine_ls_structure_factor_coef     Fsqd
_refine_ls_matrix_type     full
_refine_ls_R_factor_all     0.0592
_refine_ls_R_factor_gt     0.0424
_refine_ls_wR_factor_gt     0.1049
_refine_ls_wR_factor_ref     0.1111
_refine_ls_goodness_of_fit_ref     1.042
_refine_ls_restrained_S_all     1.042
_refine_ls_number_reflns     2823
_refine_ls_number_parameters     163
_refine_ls_number_restraints     0
_refine_ls_hydrogen_treatment     mixed
_refine_ls_weighting_scheme     calc
_refine_ls_weighting_details
                 'calc w=1/[σ²(Fo²)+(0.0672P)²] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_hydrogens     geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary     difmap
_refine_ls_shift/su_max     0.000
_refine_ls_shift/su_mean     0.000
_refine_diff_density_max     0.372
_refine_diff_density_min     -0.224
_refine_ls_extinction_method     'SHELXL97 (Sheldrick, 2008)'
_refine_ls_extinction_coef     0.020(4)
_refine_ls_extinction_expression
                                  'Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^'
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'
_computing_data_collection     'X-AREA (Stoe & Cie, 2004)'
_computing_cell_refinement     'X-AREA (Stoe & Cie, 2004)'
_computing_data_reduction     'X-RED32 (Stoe & Cie, 2004)'
_computing_structure_solution     'SHELXS97 (Sheldrick, 2008)'
_computing_structure_refinement     'SHELXL97 (Sheldrick, 2008)'
_computing_molecular_graphics
                 'PLATON (Spek, 2009) and Mercury (Macrae et al.,  2006)'
_computing_publication_material
                            'SHELXL97 (Sheldrick, 2008) and PLATON (Spek, 2009)'
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_thermal_displace_type
    _atom_site_calc_flag
    _atom_site_refinement_flags
    _atom_site_occupancy
    O O1 -0.08117(8) 1.01540(16) 0.21882(6) 0.0269(3) Uani . . 1.000
    O O2 0.03250(8) 1.27719(16) 0.06003(6) 0.0233(2) Uani . . 1.000
    N N1 -0.15978(9) 0.51231(18) 0.08046(7) 0.0216(3) Uani . . 1.000
    N N2 -0.01442(9) 0.91083(19) 0.11117(7) 0.0206(3) Uani . . 1.000
    N N3 0.42324(10) 0.8732(2) 0.16564(8) 0.0328(3) Uani . . 1.000
    C C1 -0.24525(11) 0.3491(2) 0.05116(9) 0.0253(3) Uani . . 1.000
    C C2 -0.35054(11) 0.3619(3) 0.06494(9) 0.0293(4) Uani . . 1.000
    C C3 -0.36862(11) 0.5519(3) 0.11228(10) 0.0299(4) Uani . . 1.000
    C C4 -0.28077(11) 0.7220(2) 0.14387(9) 0.0254(3) Uani . . 1.000
    C C5 -0.17819(10) 0.6966(2) 0.12589(8) 0.0206(3) Uani . . 1.000
    C C6 -0.08534(10) 0.8875(2) 0.15735(8) 0.0204(3) Uani . . 1.000
    C C7 0.06900(10) 1.1054(2) 0.12781(8) 0.0195(3) Uani . . 1.000
    C C8 0.19102(10) 1.0180(2) 0.13730(7) 0.0202(3) Uani . . 1.000
    C C9 0.26572(11) 1.1592(2) 0.11155(9) 0.0256(3) Uani . . 1.000
    C C10 0.37952(12) 1.0795(3) 0.12702(10) 0.0318(4) Uani . . 1.000
    C C11 0.34982(12) 0.7394(2) 0.19001(9) 0.0298(4) Uani . . 1.000
    C C12 0.23415(11) 0.8019(2) 0.17731(9) 0.0258(3) Uani . . 1.000
    H H1 -0.23290 0.21720 0.01910 0.0300 Uiso calc R 1.000
    H H2 -0.40940 0.24250 0.04240 0.0350 Uiso calc R 1.000
    H H2N -0.0255(14) 0.824(3) 0.0645(11) 0.026(4) Uiso . . 1.000
    H H2O -0.0220(16) 1.371(3) 0.0699(12) 0.038(5) Uiso . . 1.000
    H H3 -0.44020 0.56550 0.12300 0.0360 Uiso calc R 1.000
    H H4 -0.29040 0.85360 0.17720 0.0310 Uiso calc R 1.000
    H H7 0.07430 1.18470 0.18380 0.0230 Uiso calc R 1.000
    H H9 0.23950 1.30840 0.08370 0.0310 Uiso calc R 1.000
    H H10 0.42980 1.17870 0.10890 0.0380 Uiso calc R 1.000
    H H11 0.37860 0.59140 0.21790 0.0360 Uiso calc R 1.000
    H H12 0.18560 0.69880 0.19570 0.0310 Uiso calc R 1.000
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 0.0345(5) 0.0250(5) 0.0274(5) -0.0026(4) 0.0186(4) -0.0048(4)
    O2 0.0272(4) 0.0201(4) 0.0265(4) 0.0048(3) 0.0145(4) 0.0036(3)
    N1 0.0231(5) 0.0199(5) 0.0238(5) 0.0013(4) 0.0108(4) 0.0005(4)
    N2 0.0236(5) 0.0197(5) 0.0209(5) -0.0023(4) 0.0110(4) -0.0025(4)
    N3 0.0246(5) 0.0305(6) 0.0421(7) -0.0003(4) 0.0107(5) -0.0041(5)
    C1 0.0276(6) 0.0210(6) 0.0275(6) -0.0008(5) 0.0104(5) -0.0002(5)
    C2 0.0250(6) 0.0279(7) 0.0342(7) -0.0042(5) 0.0100(5) 0.0012(5)
    C3 0.0235(6) 0.0322(7) 0.0377(7) 0.0003(5) 0.0156(5) 0.0025(6)
    C4 0.0255(6) 0.0253(6) 0.0290(6) 0.0022(5) 0.0141(5) 0.0002(5)
    C5 0.0236(5) 0.0197(5) 0.0205(5) 0.0026(4) 0.0104(4) 0.0036(4)
    C6 0.0231(5) 0.0187(5) 0.0213(5) 0.0028(4) 0.0103(4) 0.0019(4)
    C7 0.0236(5) 0.0167(5) 0.0208(5) -0.0007(4) 0.0111(4) -0.0009(4)
    C8 0.0220(5) 0.0203(6) 0.0191(5) -0.0025(4) 0.0086(4) -0.0029(4)
    C9 0.0270(6) 0.0222(6) 0.0293(6) -0.0034(5) 0.0124(5) 0.0002(5)
    C10 0.0257(6) 0.0312(7) 0.0418(8) -0.0051(5) 0.0162(6) -0.0008(6)
    C11 0.0270(6) 0.0249(6) 0.0339(7) 0.0029(5) 0.0069(5) -0.0007(5)
    C12 0.0264(6) 0.0231(6) 0.0279(6) -0.0005(5) 0.0099(5) 0.0017(5)
_geom_special_details
;
Bond distances, angles etc. have been calculated using the rounded
fractional coordinates. All su's are estimated from the variances of the
(full) variance-covariance matrix. The cell e.s.d.'s are taken into account in
the estimation of distances, angles and torsion angles
;
loop_
    _geom_bond_atom_site_label_1
    _geom_bond_atom_site_label_2
    _geom_bond_site_symmetry_1
    _geom_bond_site_symmetry_2
    _geom_bond_distance
    _geom_bond_publ_flag
    O1 C6 . . 1.2226(15) no
    O2 C7 . . 1.4140(15) no
    O2 H2O . . 0.905(19) no
    N1 C1 . . 1.3348(17) no
    N1 C5 . . 1.3389(16) no
    N2 C7 . . 1.4452(16) no
    N2 C6 . . 1.3443(17) no
    N3 C10 . . 1.332(2) no
    N3 C11 . . 1.3328(19) no
    N2 H2N . . 0.875(17) no
    C1 C2 . . 1.379(2) no
    C2 C3 . . 1.382(2) no
    C3 C4 . . 1.383(2) no
    C4 C5 . . 1.3881(19) no
    C5 C6 . . 1.5029(17) no
    C7 C8 . . 1.5141(18) no
    C8 C9 . . 1.3807(18) no
    C8 C12 . . 1.3861(16) no
    C9 C10 . . 1.385(2) no
    C11 C12 . . 1.388(2) no
    C1 H1 . . 0.9500 no
    C2 H2 . . 0.9500 no
    C3 H3 . . 0.9500 no
    C4 H4 . . 0.9500 no
    C7 H7 . . 1.0000 no
    C9 H9 . . 0.9500 no
    C10 H10 . . 0.9500 no
    C11 H11 . . 0.9500 no
    C12 H12 . . 0.9500 no
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_2
    _geom_angle_site_symmetry_3
    _geom_angle
    _geom_angle_publ_flag
    C7 O2 H2O . . . 107.2(11) no
    C1 N1 C5 . . . 117.60(12) no
    C6 N2 C7 . . . 121.06(10) no
    C10 N3 C11 . . . 115.87(13) no
    C7 N2 H2N . . . 117.3(12) no
    C6 N2 H2N . . . 120.8(12) no
    N1 C1 C2 . . . 123.46(12) no
    C1 C2 C3 . . . 118.60(14) no
    C2 C3 C4 . . . 118.87(13) no
    C3 C4 C5 . . . 118.65(12) no
    N1 C5 C4 . . . 122.81(11) no
    C4 C5 C6 . . . 118.26(11) no
    N1 C5 C6 . . . 118.92(11) no
    N2 C6 C5 . . . 115.50(11) no
    O1 C6 C5 . . . 120.06(12) no
    O1 C6 N2 . . . 124.37(12) no
    O2 C7 N2 . . . 111.58(10) no
    O2 C7 C8 . . . 108.43(10) no
    N2 C7 C8 . . . 111.59(10) no
    C9 C8 C12 . . . 117.93(12) no
    C7 C8 C9 . . . 120.71(10) no
    C7 C8 C12 . . . 121.23(11) no
    C8 C9 C10 . . . 118.82(12) no
    N3 C10 C9 . . . 124.42(14) no
    N3 C11 C12 . . . 124.34(11) no
    C8 C12 C11 . . . 118.62(12) no
    N1 C1 H1 . . . 118.00 no
    C2 C1 H1 . . . 118.00 no
    C1 C2 H2 . . . 121.00 no
    C3 C2 H2 . . . 121.00 no
    C2 C3 H3 . . . 121.00 no
    C4 C3 H3 . . . 121.00 no
    C3 C4 H4 . . . 121.00 no
    C5 C4 H4 . . . 121.00 no
    O2 C7 H7 . . . 108.00 no
    N2 C7 H7 . . . 108.00 no
    C8 C7 H7 . . . 108.00 no
    C8 C9 H9 . . . 121.00 no
    C10 C9 H9 . . . 121.00 no
    N3 C10 H10 . . . 118.00 no
    C9 C10 H10 . . . 118.00 no
    N3 C11 H11 . . . 118.00 no
    C12 C11 H11 . . . 118.00 no
    C8 C12 H12 . . . 121.00 no
    C11 C12 H12 . . . 121.00 no
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_1
    _geom_torsion_site_symmetry_2
    _geom_torsion_site_symmetry_3
    _geom_torsion_site_symmetry_4
    _geom_torsion
    _geom_torsion_publ_flag
    C5 N1 C1 C2 . . . . 0.34(19) no
    C1 N1 C5 C4 . . . . 0.59(18) no
    C1 N1 C5 C6 . . . . -178.08(11) no
    C7 N2 C6 O1 . . . . -4.40(19) no
    C7 N2 C6 C5 . . . . 172.53(10) no
    C6 N2 C7 O2 . . . . -107.33(13) no
    C6 N2 C7 C8 . . . . 131.21(12) no
    C11 N3 C10 C9 . . . . 0.1(2) no
    C10 N3 C11 C12 . . . . 0.2(2) no
    N1 C1 C2 C3 . . . . -0.7(2) no
    C1 C2 C3 C4 . . . . 0.1(2) no
    C2 C3 C4 C5 . . . . 0.7(2) no
    C3 C4 C5 N1 . . . . -1.1(2) no
    C3 C4 C5 C6 . . . . 177.56(12) no
    N1 C5 C6 O1 . . . . -158.19(12) no
    N1 C5 C6 N2 . . . . 24.74(16) no
    C4 C5 C6 O1 . . . . 23.08(17) no
    C4 C5 C6 N2 . . . . -153.99(12) no
    O2 C7 C8 C9 . . . . 25.04(15) no
    O2 C7 C8 C12 . . . . -159.37(11) no
    N2 C7 C8 C9 . . . . 148.32(11) no
    N2 C7 C8 C12 . . . . -36.09(15) no
    C7 C8 C9 C10 . . . . 175.51(12) no
    C12 C8 C9 C10 . . . . -0.22(19) no
    C7 C8 C12 C11 . . . . -175.24(11) no
    C9 C8 C12 C11 . . . . 0.47(18) no
    C8 C9 C10 N3 . . . . -0.1(2) no
    N3 C11 C12 C8 . . . . -0.5(2) no
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 H2N N1 . 0.875(17) 2.468(18) 2.7769(16) 101.4(13) yes
    N2 H2N O2 3_575 0.875(17) 2.091(17) 2.9304(15) 160.7(16) yes
    O2 H2O N1 1_565 0.905(19) 1.92(2) 2.8056(16) 167.6(17) yes
    C7 H7 O1 2_555 1.00 2.43 3.3694(15) 157 yes
    C12 H12 O1 2_545 0.95 2.43 3.3517(17) 163 yes
data_global
_journal_date_recd_electronic     2010-06-03
_journal_date_accepted     2010-06-07
_journal_name_full     'Acta Crystallographica, Section E'
_journal_year     2010
_journal_volume     66
_journal_issue      7
_journal_page_first     o1640
_journal_page_last     o1640
_journal_paper_category     QO
_journal_coeditor_code     LH5064
_publ_contact_author_name     'Muhammad Altaf'
_publ_contact_author_address
;
Institute of Physics
University of Neuchâtel
rue Emile-Argand 11
CH-2009 Neuchâtel
Switzerland
;
_publ_contact_author_email     'muhammad.altaf@unine.ch'
_publ_contact_author_fax     ?
_publ_contact_author_phone     ?
_publ_section_title
;
rac-N-[Hydroxy(4-pyridyl)methyl]picolinamide: a hemiamidal
;
loop_
    _publ_author_name
    _publ_author_footnote
    _publ_author_address
    'Altaf, Muhammad' .
;
Institute of Physics
University of Neuchâtel
rue Emile-Argand 11
CH-2009 Neuchâtel
Switzerland
;
    'Stoeckli-Evans, Helen' .
;
Institute of Physics
University of Neuchâtel
rue Emile-Argand 11
CH-2009 Neuchâtel
Switzerland
;
