#------------------------------------------------------------------------------
#$Date: 2011-09-10 04:16:28 +0100 (Sat, 10 Sep 2011) $
#$Revision: 25271 $
#$URL: svn://www.crystallography.net/cod/cif/2/2006648.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_2006648
loop_
_publ_author_name
'Moreno-Fuquen, R.'
'Grajales-Tamayo, M.'
'do Gambardella, M. T.'
_publ_contact_author
;
    Dr Rodolfo Moreno-Fuquen
    Depto. Qu\'imica - Universidad del Valle
    Apartado 25360, Cali, Valle
    Colombia
;
_publ_section_title
;
 The 1:1 Complex Formed by 2-Picoline <i>N</i>-Oxide and
 3-Chlorobenzoic Acid
;
_journal_issue                   11
_journal_name_full               'Acta Crystallographica Section C'
_journal_page_first              1635
_journal_page_last               1637
_journal_volume                  53
_journal_year                    1997
_chemical_formula_moiety         'C6 H7 N O , C7 H5 Cl O2'
_chemical_formula_sum            'C13 H12 Cl N O3'
_chemical_formula_weight         265.69
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_H-M   'P 1 n 1'
_atom_type_scat_source
;
 International Tables for X-ray Crystallography Vol. IV (1974,  Tables 2.2.A)
;
_cell_angle_alpha                90.00
_cell_angle_beta                 92.210(10)
_cell_angle_gamma                90.00
_cell_formula_units_Z            2
_cell_length_a                   3.9241(3)
_cell_length_b                   13.0404(8)
_cell_length_c                   12.4181(5)
_cell_measurement_reflns_used    25
_cell_measurement_temperature    295
_cell_measurement_theta_max      18.49
_cell_measurement_theta_min      10.92
_cell_volume                     634.98(7)
_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 (Johnson, 1976)'
_computing_publication_material  VAXSDP
_computing_structure_refinement  'SHELXL93 (Sheldrick, 1993)'
_computing_structure_solution    'SHELXS86 (Sheldrick, 1985)'
_diffrn_ambient_temperature      295
_diffrn_measurement_device       'Enraf-Nonius CAD-4'
_diffrn_measurement_method       \w/2\q
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.000
_diffrn_reflns_av_sigmaI/netI    0.0114
_diffrn_reflns_limit_h_max       4
_diffrn_reflns_limit_h_min       0
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       0
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            1471
_diffrn_reflns_theta_max         26.28
_diffrn_reflns_theta_min         3.12
_diffrn_standards_decay_%        0.74
_diffrn_standards_interval_time  120
_diffrn_standards_number         3
_exptl_absorpt_coefficient_mu    0.30
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            Colourless
_exptl_crystal_density_diffrn    1.390
_exptl_crystal_density_meas      none
_exptl_crystal_density_method    none
_exptl_crystal_description       'Transparent prisms'
_exptl_crystal_F_000             276
_exptl_crystal_size_max          0.15
_exptl_crystal_size_mid          0.10
_exptl_crystal_size_min          0.10
_refine_diff_density_max         0.184
_refine_diff_density_min         -0.115
_refine_ls_extinction_coef       0.058(12)
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_all   1.067
_refine_ls_goodness_of_fit_obs   1.006
_refine_ls_hydrogen_treatment    'noref except HO2 ref'
_refine_ls_matrix_type           full
_refine_ls_number_parameters     167
_refine_ls_number_reflns         1471
_refine_ls_number_restraints     2
_refine_ls_restrained_S_all      1.066
_refine_ls_restrained_S_obs      1.006
_refine_ls_R_factor_all          0.0346
_refine_ls_R_factor_obs          0.0293
_refine_ls_shift/esd_max         0.000
_refine_ls_shift/esd_mean        0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_scheme
'calc w=1/[\s^2^(Fo^2^)+(0.1000P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_wR_factor_all         0.1175
_refine_ls_wR_factor_obs         0.1057
_reflns_number_observed          1352
_reflns_number_total             1471
_reflns_observed_criterion       'I > 2.0\s(I)'
_[local]_cod_data_source_file    bs1020.cif
_[local]_cod_data_source_block   default
_[local]_cod_cif_authors_sg_H-M  Pn
_[local]_cod_chemical_formula_sum_orig 'C13 H12 N O3 Cl'
_cod_database_code               2006648
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 0.1049(7) 0.0823(5) 0.0468(4) -0.0083(5) 0.0000(4) 0.0077(4)
C1 0.0568(15) 0.0486(13) 0.0541(14) -0.0081(12) -0.0056(11) 0.0056(12)
C2 0.063(2) 0.0496(14) 0.080(2) 0.0005(12) -0.016(2) 0.0148(14)
C3 0.068(2) 0.0423(12) 0.097(2) 0.0064(13) -0.005(2) -0.0052(14)
C4 0.057(2) 0.0474(13) 0.073(2) 0.0044(12) 0.0045(13) -0.0121(13)
C5 0.0488(13) 0.0408(12) 0.0495(13) -0.0059(10) 0.0035(10) -0.0030(9)
C6 0.0506(12) 0.0395(11) 0.0465(12) -0.0026(9) 0.0028(10) 0.0023(9)
C7 0.0578(15) 0.0466(12) 0.0465(13) -0.0060(11) 0.0018(11) -0.0027(10)
O1 0.098(2) 0.0665(12) 0.0482(12) -0.0035(13) 0.0103(11) -0.0056(10)
O2 0.115(2) 0.0521(10) 0.0433(9) 0.0158(12) 0.0034(12) 0.0049(8)
O3 0.114(2) 0.0573(11) 0.0439(10) 0.0089(13) 0.0002(11) 0.0046(9)
N1 0.0575(13) 0.0466(10) 0.0473(11) 0.0083(10) 0.0007(9) 0.0070(8)
C8 0.066(2) 0.0521(13) 0.065(2) -0.0026(14) 0.0018(14) 0.0130(13)
C9 0.071(2) 0.063(2) 0.077(2) -0.001(2) -0.017(2) -0.006(2)
C10 0.091(3) 0.079(2) 0.048(2) 0.013(2) -0.006(2) -0.0050(14)
C11 0.070(2) 0.073(2) 0.0539(15) 0.014(2) 0.0113(13) 0.0158(14)
C12 0.0478(13) 0.0490(12) 0.0561(13) 0.0081(11) 0.0030(11) 0.0123(11)
C13 0.071(2) 0.0505(14) 0.083(2) 0.0013(14) 0.001(2) 0.0094(15)
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
Cl1 0.9778(2) 0.16075(7) 0.15280(7) 0.0781(3) Uani d . 1 Cl
C1 1.0617(8) 0.1174(2) 0.0237(2) 0.0534(6) Uani d . 1 C
C2 1.2078(9) 0.0221(2) 0.0096(3) 0.0647(8) Uani d . 1 C
H2 1.2634(9) -0.0195(2) 0.0685(3) 0.076 Uiso calc R 1 H
C3 1.2695(10) -0.0099(2) -0.0943(4) 0.0696(8) Uani d . 1 C
H3 1.3656(10) -0.0740(2) -0.1053(4) 0.076 Uiso calc R 1 H
C4 1.1899(8) 0.0524(2) -0.1818(3) 0.0593(7) Uani d . 1 C
H4 1.2356(8) 0.0304(2) -0.2510(3) 0.076 Uiso calc R 1 H
C5 1.0414(7) 0.1480(2) -0.1664(2) 0.0463(6) Uani d . 1 C
C6 0.9766(7) 0.1805(2) -0.0621(2) 0.0455(5) Uani d . 1 C
H6 0.8771(7) 0.2441(2) -0.0506(2) 0.076 Uiso calc R 1 H
C7 0.9564(7) 0.2141(2) -0.2611(2) 0.0503(6) Uani d . 1 C
O1 1.0022(8) 0.1882(2) -0.3526(2) 0.0706(6) Uani d . 1 O
O2 0.8215(8) 0.3022(2) -0.2345(2) 0.0701(7) Uani d . 1 O
HO2 0.747(11) 0.3314(16) -0.2890(4) 0.076 Uiso calc R 1 H
O3 0.6663(8) 0.4313(2) -0.3801(2) 0.0718(7) Uani d . 1 O
N1 0.6364(6) 0.4073(2) -0.4834(2) 0.0505(5) Uani d . 1 N
C8 0.4918(10) 0.3175(2) -0.5143(3) 0.0610(7) Uani d . 1 C
H8 0.4208(10) 0.2719(2) -0.4622(3) 0.076 Uiso calc R 1 H
C9 0.4482(9) 0.2926(3) -0.6201(3) 0.0709(9) Uani d . 1 C
H9 0.3496(9) 0.2303(3) -0.6403(3) 0.076 Uiso calc R 1 H
C10 0.5510(11) 0.3604(3) -0.6971(3) 0.0729(9) Uani d . 1 C
H10 0.5216(11) 0.3448(3) -0.7700(3) 0.076 Uiso calc R 1 H
C11 0.6989(9) 0.4520(3) -0.6646(3) 0.0654(8) Uani d . 1 C
H11 0.7679(9) 0.4984(3) -0.7163(3) 0.076 Uiso calc R 1 H
C12 0.7465(7) 0.4761(2) -0.5563(2) 0.0509(6) Uani d . 1 C
C13 0.9073(10) 0.5724(2) -0.5141(3) 0.0682(8) Uani d . 1 C
H131 0.974(6) 0.6143(9) -0.5733(3) 0.076 Uiso calc R 1 H
H132 1.105(4) 0.5557(3) -0.4695(18) 0.076 Uiso calc R 1 H
H133 0.747(3) 0.6092(10) -0.4723(18) 0.076 Uiso calc R 1 H
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
C6 C1 C2 121.9(3) y
C6 C1 Cl1 118.0(2) y
C2 C1 Cl1 120.1(2) y
C1 C2 C3 118.5(3) y
C4 C3 C2 120.8(3) y
C3 C4 C5 120.0(3) y
C6 C5 C4 119.5(3) y
C6 C5 C7 121.0(2) y
C4 C5 C7 119.5(2) y
C1 C6 C5 119.3(2) y
O1 C7 O2 123.9(3) y
O1 C7 C5 123.1(3) y
O2 C7 C5 112.9(2) y
O3 N1 C8 120.2(3) y
O3 N1 C12 118.1(2) y
C8 N1 C12 121.6(3) y
N1 C8 C9 121.2(3) y
C8 C9 C10 119.4(3) y
C11 C10 C9 118.9(3) y
C10 C11 C12 121.3(3) y
N1 C12 C11 117.6(3) y
N1 C12 C13 117.6(3) y
C11 C12 C13 124.8(3) y
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_publ_flag
Cl1 C1 1.743(3) y
C1 C6 1.376(4) y
C1 C2 1.382(5) y
C2 C3 1.386(6) y
C3 C4 1.383(5) y
C4 C5 1.392(4) y
C5 C6 1.396(4) y
C5 C7 1.485(4) y
C7 O1 1.206(4) y
C7 O2 1.313(4) y
O3 N1 1.322(3) y
N1 C8 1.350(4) y
N1 C12 1.357(3) y
C8 C9 1.358(5) y
C9 C10 1.374(6) y
C10 C11 1.382(6) y
C11 C12 1.387(5) y
C12 C13 1.492(5) y