#------------------------------------------------------------------------------
#$Date: 2011-09-10 04:16:28 +0100 (Sat, 10 Sep 2011) $
#$Revision: 25271 $
#$URL: svn://www.crystallography.net/cod/cif/2/2006666.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_2006666
loop_
_publ_author_name
'Moreno-Fuquen, R.'
'Santos, R. H. De A.'
'do Gambardella, M. T.'
_publ_section_title
;
 The 1:1 Complex Formed by 3-Picoline <i>N</i>-Oxide and
 <i>p</i>-Toluic Acid
;
_journal_issue                   11
_journal_name_full               'Acta Crystallographica Section C'
_journal_page_first              1634
_journal_page_last               1635
_journal_volume                  53
_journal_year                    1997
_chemical_formula_moiety         'C6 H7 N O , C8 H8 O2'
_chemical_formula_sum            'C14 H15 N O3'
_chemical_formula_weight         245.27
_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'
_cell_angle_alpha                90.00
_cell_angle_beta                 111.000(10)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   13.6819(9)
_cell_length_b                   7.2379(3)
_cell_length_c                   14.0407(7)
_cell_measurement_reflns_used    25
_cell_measurement_temperature    295
_cell_measurement_theta_max      18.16
_cell_measurement_theta_min      9.57
_cell_volume                     1298.07(15)
_computing_cell_refinement       'CAD-4 Software'
_computing_data_collection       'CAD-4 Software (Enraf-Nonius, 1989)'
_computing_data_reduction        'VAXSDP (Frenz, 1978)'
_computing_molecular_graphics    ORTEPII
_computing_publication_material  VAXSDP
_computing_structure_refinement  SHELXL93
_computing_structure_solution    'SHELXS86 (Sheldrick, 1985)'
_diffrn_measurement_device       'Enraf-Nonius CAD-4'
_diffrn_measurement_method       \w/2\q
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         xray_tube
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0152
_diffrn_reflns_av_sigmaI/netI    0.0191
_diffrn_reflns_limit_h_max       0
_diffrn_reflns_limit_h_min       -17
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       0
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            2740
_diffrn_reflns_theta_max         26.29
_diffrn_reflns_theta_min         2.94
_diffrn_standards_decay_%        1.13
_diffrn_standards_interval_time  120
_diffrn_standards_number         3
_exptl_absorpt_coefficient_mu    0.089
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.255
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       transparent_prism
_exptl_crystal_F_000             520
_exptl_crystal_size_max          0.18
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.10
_refine_diff_density_max         0.197
_refine_diff_density_min         -0.244
_refine_ls_extinction_coef       0.015(3)
_refine_ls_extinction_method     'SHELXL93 (Sheldrick, 1993)'
_refine_ls_goodness_of_fit_all   1.121
_refine_ls_goodness_of_fit_obs   1.067
_refine_ls_hydrogen_treatment    noref_except_HO2
_refine_ls_matrix_type           full
_refine_ls_number_parameters     169
_refine_ls_number_reflns         1844
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.125
_refine_ls_restrained_S_obs      1.067
_refine_ls_R_factor_all          0.0761
_refine_ls_R_factor_obs          0.0460
_refine_ls_shift/esd_max         0.005
_refine_ls_shift/esd_mean        0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_scheme
'1/[\s^2^(Fo^2^) + (0.0813P)^2^+0.2843P], P = (Fo^2^+2Fc^2^)/3'
_refine_ls_wR_factor_all         0.1688
_refine_ls_wR_factor_obs         0.1324
_reflns_number_observed          1844
_reflns_number_total             2629
_reflns_observed_criterion       >2sigma(I)
_[local]_cod_data_source_file    fg1302.cif
_[local]_cod_data_source_block   molecule
_[local]_cod_cif_authors_sg_H-M  'P 21/c'
_cod_original_cell_volume        1298.11(12)
_cod_database_code               2006666
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_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
C1 0.0619(12) 0.0426(11) 0.0600(12) 0.0007(9) 0.0180(10) 0.0007(9)
C2 0.0532(11) 0.0570(12) 0.0606(11) 0.0005(9) 0.0200(9) 0.0044(9)
C3 0.0581(12) 0.0697(15) 0.0634(13) -0.0115(11) 0.0128(10) -0.0045(11)
C4 0.0776(15) 0.0534(13) 0.081(2) -0.0134(11) 0.0260(13) -0.0175(11)
C5 0.0595(12) 0.0410(10) 0.0830(14) -0.0012(9) 0.0289(11) -0.0012(10)
C6 0.085(2) 0.074(2) 0.080(2) 0.0217(13) 0.0162(14) 0.0138(13)
N1 0.0480(8) 0.0438(9) 0.0616(10) -0.0057(7) 0.0159(7) 0.0028(7)
O1 0.0582(8) 0.0559(9) 0.0803(10) -0.0085(7) -0.0013(7) 0.0117(7)
C7 0.0503(10) 0.0482(11) 0.0574(11) 0.0003(8) 0.0150(9) -0.0047(9)
C8 0.0474(10) 0.0510(11) 0.0551(11) -0.0019(8) 0.0154(8) -0.0048(8)
C9 0.0533(12) 0.0569(13) 0.097(2) 0.0018(10) 0.0113(12) 0.0020(12)
C10 0.0453(11) 0.077(2) 0.107(2) 0.0003(11) 0.0111(12) -0.0031(15)
C11 0.0551(12) 0.0736(15) 0.0718(13) -0.0154(11) 0.0200(10) -0.0103(11)
C12 0.0656(13) 0.0522(12) 0.087(2) -0.0089(10) 0.0192(12) -0.0078(11)
C13 0.0506(11) 0.0535(12) 0.0780(14) 0.0005(9) 0.0156(10) -0.0056(10)
C14 0.0686(15) 0.093(2) 0.106(2) -0.0293(14) 0.0229(14) -0.014(2)
O2 0.0548(9) 0.0499(9) 0.1139(14) -0.0047(7) 0.0019(9) 0.0077(9)
O3 0.0501(8) 0.0568(9) 0.0888(11) 0.0003(7) 0.0034(7) -0.0020(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_refinement_flags
_atom_site_occupancy
_atom_site_type_symbol
C1 1.0569(2) 0.3623(3) 0.3738(2) 0.0559(5) Uani d . 1 C
H1 1.0392(2) 0.2544(3) 0.3355(2) 0.076 Uiso calc R 1 H
C2 1.1449(2) 0.3650(3) 0.4614(2) 0.0570(5) Uani d . 1 C
C3 1.1689(2) 0.5270(3) 0.5164(2) 0.0662(6) Uani d . 1 C
H3 1.2274(2) 0.5331(3) 0.5761(2) 0.076 Uiso calc R 1 H
C4 1.1063(2) 0.6797(3) 0.4828(2) 0.0713(6) Uani d . 1 C
H4 1.1227(2) 0.7889(3) 0.5200(2) 0.076 Uiso calc R 1 H
C5 1.0201(2) 0.6721(3) 0.3949(2) 0.0603(5) Uani d . 1 C
H5 0.9785(2) 0.7762(3) 0.3717(2) 0.076 Uiso calc R 1 H
C6 1.2096(2) 0.1941(4) 0.4940(2) 0.0832(8) Uani d . 1 C
H61 1.1989(9) 0.1417(11) 0.5523(7) 0.076 Uiso calc R 1 H
H62 1.2822(2) 0.2246(5) 0.5114(10) 0.076 Uiso calc R 1 H
H63 1.1893(8) 0.1062(8) 0.4391(4) 0.076 Uiso calc R 1 H
N1 0.99628(12) 0.5131(2) 0.34277(12) 0.0522(4) Uani d . 1 N
O1 0.91213(12) 0.5069(2) 0.25798(13) 0.0720(5) Uani d . 1 O
C7 0.77886(15) 0.1079(3) 0.2456(2) 0.0531(5) Uani d . 1 C
C8 0.68449(14) -0.0110(3) 0.20418(15) 0.0520(5) Uani d . 1 C
C9 0.5855(2) 0.0614(4) 0.1565(2) 0.0734(7) Uani d . 1 C
H9 0.5764(2) 0.1887(4) 0.1492(2) 0.076 Uiso calc R 1 H
C10 0.5000(2) -0.0546(4) 0.1195(2) 0.0811(7) Uani d . 1 C
H10 0.4336(2) -0.0039(4) 0.0887(2) 0.076 Uiso calc R 1 H
C11 0.5108(2) -0.2441(4) 0.1273(2) 0.0676(6) Uani d . 1 C
C12 0.6093(2) -0.3141(3) 0.1748(2) 0.0703(6) Uani d . 1 C
H12 0.6183(2) -0.4414(3) 0.1814(2) 0.076 Uiso calc R 1 H
C13 0.6957(2) -0.2006(3) 0.2129(2) 0.0627(6) Uani d . 1 C
H13 0.7618(2) -0.2520(3) 0.2447(2) 0.076 Uiso calc R 1 H
C14 0.4172(2) -0.3701(4) 0.0832(2) 0.0914(9) Uani d . 1 C
H141 0.4408(2) -0.4948(5) 0.0826(10) 0.076 Uiso calc R 1 H
H142 0.3771(6) -0.3321(13) 0.0148(5) 0.076 Uiso calc R 1 H
H143 0.3744(6) -0.3633(16) 0.1243(7) 0.076 Uiso calc R 1 H
O2 0.76113(13) 0.2827(2) 0.21913(15) 0.0806(6) Uani d . 1 O
H2 0.8216(19) 0.347(4) 0.2413(19) 0.076 Uiso d . 1 H
O3 0.86361(11) 0.0516(2) 0.29953(13) 0.0711(5) Uani d . 1 O
loop_
_atom_type_symbol
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C .017 .009 International_Tables_Vol_IV_Table_2.3.1
H 0 0 International_Tables_Vol_IV_Table_2.3.1
O .047 .032 International_Tables_Vol_IV_Table_2.3.1
N .029 .018 International_Tables_Vol_IV_Table_2.3.1
loop_
_diffrn_standard_refln_index_h
_diffrn_standard_refln_index_k
_diffrn_standard_refln_index_l
2 -1 -2
1 2 10
0 11 -3
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
N1 C1 C2 121.2(2) ?
N1 C1 H1 119.41(11) ?
C2 C1 H1 119.41(12) ?
C3 C2 C1 117.9(2) ?
C3 C2 C6 122.5(2) y
C1 C2 C6 119.6(2) y
C4 C3 C2 119.9(2) ?
C4 C3 H3 120.06(13) ?
C2 C3 H3 120.06(13) ?
C5 C4 C3 120.5(2) ?
C5 C4 H4 119.76(13) ?
C3 C4 H4 119.76(13) ?
N1 C5 C4 119.3(2) ?
N1 C5 H5 120.37(12) ?
C4 C5 H5 120.37(13) ?
C2 C6 H61 109.47(14) ?
C2 C6 H62 109.47(14) ?
H61 C6 H62 109.5 ?
C2 C6 H63 109.47(14) ?
H61 C6 H63 109.5 ?
H62 C6 H63 109.5 ?
O1 N1 C5 118.8(2) y
O1 N1 C1 119.9(2) ?
C5 N1 C1 121.2(2) ?
O3 C7 O2 122.7(2) ?
O3 C7 C8 123.7(2) y
O2 C7 C8 113.6(2) y
C9 C8 C13 118.6(2) ?
C9 C8 C7 122.2(2) y
C13 C8 C7 119.2(2) y
C8 C9 C10 120.2(2) ?
C8 C9 H9 119.91(13) ?
C10 C9 H9 119.91(15) ?
C11 C10 C9 121.5(2) ?
C11 C10 H10 119.26(13) ?
C9 C10 H10 119.26(15) ?
C12 C11 C10 117.8(2) ?
C12 C11 C14 121.2(2) y
C10 C11 C14 121.1(2) y
C11 C12 C13 121.7(2) ?
C11 C12 H12 119.15(14) ?
C13 C12 H12 119.15(14) ?
C12 C13 C8 120.3(2) ?
C12 C13 H13 119.85(14) ?
C8 C13 H13 119.85(12) ?
C11 C14 H141 109.5(2) ?
C11 C14 H142 109.5(2) ?
H141 C14 H142 109.5 ?
C11 C14 H143 109.5(2) ?
H141 C14 H143 109.5 ?
H142 C14 H143 109.5 ?
C7 O2 H2 110.2(16) ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_publ_flag
C1 N1 1.346(2) y
C1 C2 1.379(3) ?
C1 H1 0.93 ?
C2 C3 1.377(3) ?
C2 C6 1.494(3) y
C3 C4 1.374(3) ?
C3 H3 0.93 ?
C4 C5 1.369(3) ?
C4 H4 0.93 ?
C5 N1 1.340(3) ?
C5 H5 0.93 ?
C6 H61 0.96 ?
C6 H62 0.96 ?
C6 H63 0.96 ?
N1 O1 1.328(2) y
C7 O3 1.206(2) y
C7 O2 1.316(3) y
C7 C8 1.486(3) y
C8 C9 1.381(3) ?
C8 C13 1.381(3) ?
C9 C10 1.382(3) ?
C9 H9 0.93 ?
C10 C11 1.379(4) ?
C10 H10 0.93 ?
C11 C12 1.369(3) ?
C11 C14 1.512(3) y
C12 C13 1.380(3) ?
C12 H12 0.93 ?
C13 H13 0.93 ?
C14 H141 0.96 ?
C14 H142 0.96 ?
C14 H143 0.96 ?
O2 H2 0.90(3) y