#------------------------------------------------------------------------------
#$Date: 2011-09-10 04:16:28 +0100 (Sat, 10 Sep 2011) $
#$Revision: 25271 $
#$URL: svn://www.crystallography.net/cod/cif/2/2008208.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_2008208
loop_
_publ_author_name
'Foces-Foces, C.'
'Llamas-Saiz, A. L.'
'Lorente, P.'
'Golubev, N. S.'
'Limbach, H.-H.'
_publ_section_title
;
 Three 2,4,6-trimethylpyridine--benzoic acid complexes at 150K
;
_journal_issue                   3
_journal_name_full               'Acta Crystallographica Section C'
_journal_page_first              377
_journal_page_last               381
_journal_volume                  55
_journal_year                    1999
_chemical_formula_moiety         'C8 H11 N, C7 H6 O2'
_chemical_formula_sum            'C15 H17 N O2'
_chemical_formula_weight         243.305
_chemical_melting_point          339
_chemical_name_systematic        '2,4,6-Trymethylpyridine benzoic acid'
_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'
_audit_creation_method           from_xtal_archive_file_using_CIFIO
_cell_angle_alpha                90.00000
_cell_angle_beta                 92.702(7)
_cell_angle_gamma                90.00000
_cell_formula_units_Z            4
_cell_length_a                   7.4875(6)
_cell_length_b                   14.4756(14)
_cell_length_c                   12.1879(12)
_cell_measurement_reflns_used    66
_cell_measurement_temperature    150
_cell_measurement_theta_max      45
_cell_measurement_theta_min      2
_cell_volume                     1319.5(2)
_computing_cell_refinement       'LSUCRE (Appleman, 1984)'
_computing_data_collection       'Philips PW1100 (Hornstra & Vossers, 1973)'
_computing_data_reduction
'xtal_DIFDAT_SORTRF_ADDREF  (Hall et al., 1992)'
_computing_molecular_graphics    xtal_ORTEP
_computing_publication_material  xtal_BONDLA_CIFIO
_computing_structure_refinement  'xtal CRYLSQ'
_computing_structure_solution    'SIR92 (Altomare et al., 1994)'
_diffrn_ambient_temperature      150
_diffrn_measurement_device       'Philips PW1100 diffractometer'
_diffrn_measurement_method       '\w/2\q scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'scaled tube'
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.5418
_diffrn_reflns_av_R_equivalents  .054
_diffrn_reflns_av_sigmaI/netI    .014
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       0
_diffrn_reflns_limit_k_max       0
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            2482
_diffrn_reflns_reduction_process perpendicular_monochr_Lp
_diffrn_reflns_theta_max         64.47
_diffrn_reflns_theta_min         4.75
_diffrn_standards_decay_%        9
_diffrn_standards_interval_time  90
_diffrn_standards_number         2
_exptl_absorpt_coefficient_mu    0.6489
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.225
_exptl_crystal_density_meas      None
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       'rectangular prism'
_exptl_crystal_F_000             520
_exptl_crystal_size_max          0.46
_exptl_crystal_size_mid          0.43
_exptl_crystal_size_min          0.37
_refine_diff_density_max         .30
_refine_diff_density_min         -.39
_refine_ls_abs_structure_details ' not applicable '
_refine_ls_extinction_coef       204(11)
_refine_ls_extinction_method     Zachariasen
_refine_ls_goodness_of_fit_all   .992
_refine_ls_goodness_of_fit_obs   1.00
_refine_ls_hydrogen_treatment    noref
_refine_ls_matrix_type           full
_refine_ls_number_constraints    0
_refine_ls_number_parameters     168
_refine_ls_number_reflns         1723
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          .083
_refine_ls_R_factor_obs          .068
_refine_ls_shift/esd_max         .009
_refine_ls_structure_factor_coef F
_refine_ls_weighting_scheme      'w = k{(A + BFo)^2^[C + D(sin\q)/\l]}^-1^'
_refine_ls_wR_factor_all         .103
_refine_ls_wR_factor_obs         .091
_reflns_number_observed          1723
_reflns_number_total             2202
_reflns_observed_criterion       refl_observed_if_I____>2.000_sigma(I___)
_[local]_cod_data_source_file    bm1262.cif
_[local]_cod_data_source_block   I
_[local]_cod_cif_authors_sg_H-M  P21/c
_[local]_cod_cif_authors_sg_Hall -P_2ybc
_cod_depositor_comments
;
The following automatic conversions were performed:

'_exptl_absorpt_correction_type' value 'None' changed to 'none'
according to /home/saulius/struct/CIF-dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.1 from 2010-06-29.

Automatic conversion script
Id: cif_fix_values 1715 2011-07-08 13:25:40Z adriana 
;
_cod_database_code               2008208
loop_
_symmetry_equiv_pos_as_xyz
+x,+y,+z
-x,1/2+y,1/2-z
-x,-y,-z
+x,1/2-y,1/2+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
N1 .0300(10) .038(2) .0330(10) -.0020(10) -.0060(10) .0010(10)
C2 .030(2) .044(2) .032(2) -.0010(10) -.0050(10) .0000(10)
C3 .035(2) .042(2) .034(2) -.0010(10) -.0030(10) .0050(10)
C4 .040(2) .039(2) .040(2) .0010(10) -.0090(10) .004(2)
C5 .037(2) .044(2) .035(2) .002(2) -.0070(10) .0000(10)
C6 .031(2) .044(2) .031(2) -.0030(10) -.0080(10) .0020(10)
C7 .045(2) .048(2) .042(2) .003(2) .002(2) -.004(2)
C8 .072(3) .041(2) .058(3) .003(2) .001(2) .003(2)
C9 .052(2) .048(2) .036(2) -.002(2) .002(2) .005(2)
C10 .033(2) .039(2) .039(2) .0020(10) -.0060(10) -.002(2)
C11 .030(2) .036(2) .035(2) .0030(10) -.0080(10) -.0030(10)
C12 .036(2) .040(2) .038(2) .0030(10) -.0080(10) -.0020(10)
C13 .044(2) .040(2) .043(2) .000(2) -.002(2) .005(2)
C14 .034(2) .037(2) .057(2) .001(2) -.002(2) .002(2)
C15 .034(2) .042(2) .053(2) -.001(2) -.010(2) -.011(2)
C16 .039(2) .043(2) .038(2) .004(2) -.0100(10) -.002(2)
O17 .054(2) .0390(10) .0450(10) -.0060(10) -.0180(10) -.0010(10)
O18 .076(2) .046(2) .0380(10) -.0040(10) -.0170(10) .0060(10)
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
N1 .6489(4) .4047(2) .0938(2) .0340(10) Uani
C2 .5842(4) .3525(3) .1755(3) .035(2) Uani
C3 .5832(5) .2581(3) .1708(3) .038(2) Uani
C4 .6507(5) .2121(3) .0811(3) .040(2) Uani
C5 .7161(5) .2667(3) -.0024(3) .039(2) Uani
C6 .7133(4) .3614(3) .0058(3) .036(2) Uani
C7 .5177(5) .4049(3) .2715(3) .045(2) Uani
C8 .6549(7) .1088(3) .0758(4) .057(2) Uani
C9 .7822(5) .4223(3) -.0825(3) .045(2) Uani
C10 .7835(5) .6221(3) .1766(3) .037(2) Uani
C11 .8345(4) .7200(2) .1567(3) .034(2) Uani
C12 .8023(5) .7617(3) .0541(3) .038(2) Uani
C13 .8574(5) .8525(3) .0369(3) .043(2) Uani
C14 .9416(5) .9018(3) .1209(3) .043(2) Uani
C15 .9721(5) .8615(3) .2238(3) .044(2) Uani
C16 .9200(5) .7708(3) .2407(3) .040(2) Uani
O17 .6935(4) .5837(2) .0938(2) .0470(10) Uani
O18 .8236(4) .5819(2) .2622(2) .054(2) Uani
H3 .54370 .22205 .23307 .03734 Uiso
H5 .75489 .23645 -.06710 .03843 Uiso
H71 .41444 .43830 .24861 .04491 Uiso
H72 .59226 .46078 .29356 .04491 Uiso
H73 .48284 .36302 .33714 .04491 Uiso
H81 .54546 .08706 .08836 .05735 Uiso
H82 .69721 .07957 .00600 .05735 Uiso
H83 .72300 .08236 .13212 .05735 Uiso
H91 .89889 .45631 -.05228 .04539 Uiso
H92 .70817 .47354 -.10347 .04539 Uiso
H93 .80274 .38648 -.15235 .04539 Uiso
H12 .74816 .72552 .00166 .03781 Uiso
H13 .83783 .88505 -.03382 .04252 Uiso
H14 .97733 .96618 .11303 .04260 Uiso
H15 1.03261 .89483 .28428 .04298 Uiso
H16 .93771 .73705 .30892 .03994 Uiso
H17 .681(6) .509(3) .098(4) .030(10) Uiso
loop_
_atom_type_symbol
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C .017 .009 International_Tables_for_Crystallography_(1974)
H 0 0 International_Tables_for_Crystallography_(1974)
N .029 .018 International_Tables_for_Crystallography_(1974)
O .047 .032 International_Tables_for_Crystallography_(1974)
loop_
_diffrn_standard_refln_index_h
_diffrn_standard_refln_index_k
_diffrn_standard_refln_index_l
1 -1 2
-1 1 -2
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 N1 C2 118.5(3) yes
N1 C2 C3 121.8(3) ?
N1 C2 C7 115.8(3) ?
C3 C2 C7 122.5(3) ?
H3 C3 C2 120.1(3) ?
H3 C3 C4 119.2(4) ?
C2 C3 C4 120.5(3) ?
C3 C4 C5 117.0(3) ?
C3 C4 C8 121.3(4) ?
C5 C4 C8 121.7(4) ?
H5 C5 C6 121.4(4) ?
H5 C5 C4 118.2(4) ?
C6 C5 C4 120.3(3) ?
N1 C6 C5 121.8(3) ?
N1 C6 C9 116.4(3) ?
C5 C6 C9 121.8(3) ?
H71 C7 H73 107.0(4) ?
H71 C7 H72 95.8(4) ?
H71 C7 C2 109.1(3) ?
H73 C7 H72 114.4(4) ?
H73 C7 C2 114.1(3) ?
H72 C7 C2 114.3(4) ?
H81 C8 H83 101.9(5) ?
H81 C8 H82 108.7(4) ?
H81 C8 C4 108.8(4) ?
H83 C8 H82 105.6(4) ?
H83 C8 C4 113.3(4) ?
H82 C8 C4 117.5(4) ?
H92 C9 H93 106.3(3) ?
H92 C9 H91 101.1(4) ?
H92 C9 C6 115.7(4) ?
H93 C9 H91 112.1(4) ?
H93 C9 C6 111.9(3) ?
H91 C9 C6 109.4(3) ?
O18 C10 O17 123.6(3) yes
O18 C10 C11 122.6(3) yes
O17 C10 C11 113.8(3) yes
C16 C11 C12 118.9(3) yes
C16 C11 C10 119.6(3) ?
C12 C11 C10 121.4(3) ?
H12 C12 C13 124.3(4) ?
H12 C12 C11 115.7(4) ?
C13 C12 C11 120.1(3) ?
H13 C13 C14 116.5(4) ?
H13 C13 C12 123.2(4) ?
C14 C13 C12 120.3(3) ?
H14 C14 C13 122.7(4) ?
H14 C14 C15 117.0(4) ?
C13 C14 C15 120.2(3) ?
H15 C15 C16 118.7(4) ?
H15 C15 C14 121.7(4) ?
C16 C15 C14 119.6(3) ?
H16 C16 C15 125.2(4) ?
H16 C16 C11 113.9(4) ?
C15 C16 C11 120.9(3) ?
H17 O17 C10 115(2) ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_publ_flag
N1 C6 1.351(4) yes
N1 C2 1.357(4) yes
C2 C3 1.369(5) ?
C2 C7 1.498(5) ?
C3 H3 .978(4) ?
C3 C4 1.395(5) ?
C4 C5 1.395(5) ?
C4 C8 1.498(6) ?
C5 H5 .959(4) ?
C5 C6 1.375(5) ?
C6 C9 1.500(5) ?
C7 H71 .943(4) ?
C7 H73 1.047(4) ?
C7 H72 1.014(4) ?
C8 H81 .898(5) ?
C8 H83 .919(5) ?
C8 H82 1.014(5) ?
C9 H92 .954(4) ?
C9 H93 1.015(4) ?
C9 H91 1.054(4) ?
C10 O18 1.219(5) yes
C10 O17 1.310(4) yes
C10 C11 1.491(5) yes
C11 C16 1.391(5) ?
C11 C12 1.398(5) ?
C12 H12 .908(4) ?
C12 C13 1.396(5) ?
C13 H13 .987(4) ?
C13 C14 1.376(5) ?
C14 H14 .975(4) ?
C14 C15 1.392(6) ?
C15 H15 .974(4) ?
C15 C16 1.388(5) ?
C16 H16 .968(4) ?
O17 H17 1.09(5) ?
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
O17 H17 N1 . 1.09(5) 1.53(5) 2.613(4) 174(4) yes
C7 H72 O18 . 1.01 2.51 3.443(5) 154 yes
C13 H13 O18 4_564 0.99 2.53 3.478(5) 161 yes
C14 H14 O18 2_755 0.98 2.67 3.418(5) 134 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
_geom_torsion_publ_flag
C6 N1 C2 C3 .2(5) ?
C6 N1 C2 C7 179.1(3) ?
C2 N1 C6 C5 -.6(5) ?
C2 N1 C6 C9 179.6(3) ?
N1 C2 C3 C4 .5(5) ?
N1 C2 C3 H3 175.6(3) ?
C7 C2 C3 C4 -178.3(3) ?
C7 C2 C3 H3 -3.2(5) ?
N1 C2 C7 H71 67.3(4) ?
N1 C2 C7 H72 -38.7(5) ?
N1 C2 C7 H73 -173.1(3) ?
C3 C2 C7 H71 -113.8(4) ?
C3 C2 C7 H72 140.2(4) ?
C3 C2 C7 H73 5.8(5) ?
C2 C3 C4 C5 -.7(5) ?
C2 C3 C4 C8 178.5(4) ?
H3 C3 C4 C5 -175.9(3) ?
H3 C3 C4 C8 3.3(6) ?
C3 C4 C5 C6 .3(5) ?
C3 C4 C5 H5 -175.5(3) ?
C8 C4 C5 C6 -178.9(4) ?
C8 C4 C5 H5 5.3(6) ?
C3 C4 C8 H81 51.7(6) ?
C3 C4 C8 H82 175.6(4) ?
C3 C4 C8 H83 -60.8(6) ?
C5 C4 C8 H81 -129.1(4) ?
C5 C4 C8 H82 -5.2(6) ?
C5 C4 C8 H83 118.4(5) ?
C4 C5 C6 N1 .3(5) ?
C4 C5 C6 C9 -179.9(3) ?
H5 C5 C6 N1 176.0(3) ?
H5 C5 C6 C9 -4.3(6) ?
N1 C6 C9 H91 67.7(4) ?
N1 C6 C9 H92 -45.6(5) ?
N1 C6 C9 H93 -167.5(3) ?
C5 C6 C9 H91 -112.1(4) ?
C5 C6 C9 H92 134.7(4) ?
C5 C6 C9 H93 12.7(5) ?
O17 C10 C11 C12 -5.9(5) yes
O17 C10 C11 C16 175.7(3) ?
O18 C10 C11 C12 173.7(4) yes
O18 C10 C11 C16 -4.7(5) ?
C11 C10 O17 H17 167(3) ?
O18 C10 O17 H17 -13(3) ?
C10 C11 C12 C13 -177.7(3) ?
C10 C11 C12 H12 .5(5) ?
C16 C11 C12 C13 .7(5) ?
C16 C11 C12 H12 178.9(3) ?
C10 C11 C16 C15 178.8(3) ?
C10 C11 C16 H16 -1.4(5) ?
C12 C11 C16 C15 .3(5) ?
C12 C11 C16 H16 -179.8(3) ?
C11 C12 C13 C14 -.8(6) ?
C11 C12 C13 H13 -180.0(4) ?
H12 C12 C13 C14 -178.8(4) ?
H12 C12 C13 H13 2.0(7) ?
C12 C13 C14 C15 -.2(6) ?
C12 C13 C14 H14 -177.2(4) ?
H13 C13 C14 C15 179.1(4) ?
H13 C13 C14 H14 2.0(6) ?
C13 C14 C15 C16 1.2(6) ?
C13 C14 C15 H15 179.3(4) ?
H14 C14 C15 C16 178.4(3) ?
H14 C14 C15 H15 -3.5(6) ?
C14 C15 C16 C11 -1.3(6) ?
C14 C15 C16 H16 178.9(4) ?
H15 C15 C16 C11 -179.4(3) ?
H15 C15 C16 H16 .7(6) ?