#------------------------------------------------------------------------------
#$Date: 2011-09-10 05:16:28 +0200 (Sat, 10 Sep 2011) $
#$Revision: 25271 $
#$URL: svn://www.crystallography.net/cod/cif/2/2009097.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_2009097
loop_
_publ_author_name
'Freytag, M.'
'Jones, P. G.'
_publ_section_title
;
 Hydrogen bonding in two piperidinium derivatives
;
_journal_issue                   11
_journal_name_full               'Acta Crystallographica Section C'
_journal_page_first              1874
_journal_page_last               1877
_journal_volume                  55
_journal_year                    1999
_chemical_formula_moiety         'C6 H14 N 1+, C7 H12 N O2 1-, H2 O'
_chemical_formula_sum            'C13 H28 N2 O3'
_chemical_formula_weight         260.37
_chemical_name_systematic
;
 4-Methylpiperidinium 4-Methylpyridine-N-carboxylate Monohydrate
;
_space_group_IT_number           61
_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_Hall  '-P 2ac 2ab'
_symmetry_space_group_name_H-M   'P b c a'
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_formula_units_Z            8
_cell_length_a                   9.1378(10)
_cell_length_b                   10.9924(14)
_cell_length_c                   30.580(3)
_cell_measurement_reflns_used    45
_cell_measurement_temperature    173(2)
_cell_measurement_theta_max      11.9
_cell_measurement_theta_min      4.8
_cell_volume                     3071.6(6)
_computing_cell_refinement       XSCANS
_computing_data_collection       'XSCANS (Fait, 1991)'
_computing_data_reduction        XSCANS
_computing_molecular_graphics    'XP (Siemens, 1994b)'
_computing_publication_material  SHELXL97
_computing_structure_refinement  'SHELXL97 (Sheldrick, 1997a)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 1997b)'
_diffrn_ambient_temperature      173(2)
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_device_type  'Siemens P4'
_diffrn_measurement_method       \w
_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  0.029
_diffrn_reflns_av_sigmaI/netI    0.0767
_diffrn_reflns_limit_h_max       0
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       2
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       0
_diffrn_reflns_limit_l_min       -36
_diffrn_reflns_number            3094
_diffrn_reflns_theta_full        25.00
_diffrn_reflns_theta_max         25
_diffrn_reflns_theta_min         3.19
_diffrn_standards_decay_%        0
_diffrn_standards_interval_count 247
_diffrn_standards_number         3
_exptl_absorpt_coefficient_mu    0.079
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.126
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       cone
_exptl_crystal_F_000             1152
_exptl_crystal_size_max          0.4
_exptl_crystal_size_mid          0.3
_exptl_crystal_size_min          0.3
_refine_diff_density_max         0.12
_refine_diff_density_min         -0.13
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.797
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     181
_refine_ls_number_reflns         2694
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.797
_refine_ls_R_factor_all          0.088
_refine_ls_R_factor_gt           0.038
_refine_ls_shift/su_max          <0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w = 1/[\s^2^(Fo^2^)+(0.0346P)^2^] where P = (Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_ref         0.078
_reflns_number_gt                1486
_reflns_number_total             2694
_reflns_threshold_expression     I>2\s(I)
_[local]_cod_data_source_file    bm1355.cif
_[local]_cod_data_source_block   secondo
_cod_depositor_comments
;
The following automatic conversions were performed:

'_geom_torsion_publ_flag' value 'Y' changed to 'y' according to
/home/saulius/struct/CIF-dictionaries/cif_core.dic dictionary named
'cif_core.dic' version 2.4.1 from 2010-06-29 (19 times).

Automatic conversion script
Id: cif_fix_values 1715 2011-07-08 13:25:40Z adriana 
;
_cod_database_code               2009097
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'-x, y+1/2, -z+1/2'
'x+1/2, -y+1/2, -z'
'-x, -y, -z'
'x-1/2, y, -z-1/2'
'x, -y-1/2, z-1/2'
'-x-1/2, y-1/2, z'
loop_
_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
_atom_site_type_symbol
N2 0.45401(17) 0.78859(15) 0.27488(5) 0.0305(4) Uani d . 1 N
H1 0.442(2) 0.8071(18) 0.2409(7) 0.066(7) Uiso d . 1 H
H2 0.514(2) 0.7175(18) 0.2797(6) 0.053(6) Uiso d . 1 H
C11 0.5309(2) 0.89423(16) 0.29484(5) 0.0350(5) Uani d . 1 C
H11A 0.4759 0.9697 0.2884 0.042 Uiso calc R 1 H
H11B 0.6296 0.9021 0.2818 0.042 Uiso calc R 1 H
C12 0.5447(2) 0.87875(17) 0.34388(5) 0.0350(5) Uani d . 1 C
H12A 0.5914 0.9521 0.3565 0.042 Uiso calc R 1 H
H12B 0.6087 0.8082 0.3502 0.042 Uiso calc R 1 H
C13 0.3968(2) 0.85914(18) 0.36547(5) 0.0350(5) Uani d . 1 C
H13 0.3354 0.9328 0.3600 0.042 Uiso calc R 1 H
C14 0.3221(2) 0.7506(2) 0.34420(6) 0.0411(5) Uani d . 1 C
H14A 0.2234 0.7402 0.3570 0.049 Uiso calc R 1 H
H14B 0.3792 0.6761 0.3504 0.049 Uiso calc R 1 H
C15 0.30843(19) 0.7672(2) 0.29486(6) 0.0414(5) Uani d . 1 C
H15A 0.2638 0.6936 0.2818 0.050 Uiso calc R 1 H
H15B 0.2436 0.8372 0.2886 0.050 Uiso calc R 1 H
C16 0.4114(2) 0.8429(2) 0.41474(6) 0.0507(6) Uani d . 1 C
H16A 0.4700 0.7702 0.4209 0.061 Uiso calc R 1 H
H16B 0.3140 0.8337 0.4277 0.061 Uiso calc R 1 H
H16C 0.4597 0.9144 0.4273 0.061 Uiso calc R 1 H
O3 0.65133(16) 0.59730(14) 0.28722(5) 0.0430(4) Uani d . 1 O
H1W 0.624(2) 0.520(2) 0.2969(6) 0.073(8) Uiso d . 1 H
H2W 0.734(3) 0.624(2) 0.3016(7) 0.080(8) Uiso d . 1 H
O1 0.59863(15) 0.17202(11) 0.32675(4) 0.0422(4) Uani d . 1 O
O2 0.56788(14) 0.36700(11) 0.30788(4) 0.0390(4) Uani d . 1 O
N1 0.55769(17) 0.31223(13) 0.37923(4) 0.0328(4) Uani d . 1 N
C1 0.5230(2) 0.43512(16) 0.39358(5) 0.0357(5) Uani d . 1 C
H1A 0.4199 0.4384 0.4035 0.043 Uiso calc R 1 H
H1B 0.5341 0.4921 0.3687 0.043 Uiso calc R 1 H
C2 0.6228(2) 0.47397(16) 0.43060(5) 0.0347(5) Uani d . 1 C
H2A 0.5905 0.5543 0.4416 0.042 Uiso calc R 1 H
H2B 0.7236 0.4832 0.4192 0.042 Uiso calc R 1 H
C3 0.6240(2) 0.38343(17) 0.46830(5) 0.0357(5) Uani d . 1 C
H3 0.5241 0.3825 0.4816 0.043 Uiso calc R 1 H
C4 0.6559(2) 0.25681(18) 0.45082(6) 0.0381(5) Uani d . 1 C
H4A 0.7583 0.2536 0.4404 0.046 Uiso calc R 1 H
H4B 0.6454 0.1971 0.4749 0.046 Uiso calc R 1 H
C5 0.5543(2) 0.22174(17) 0.41369(6) 0.0376(5) Uani d . 1 C
H5A 0.5843 0.1419 0.4017 0.045 Uiso calc R 1 H
H5B 0.4531 0.2139 0.4250 0.045 Uiso calc R 1 H
C6 0.7329(2) 0.4210(2) 0.50373(6) 0.0532(6) Uani d . 1 C
H6A 0.8324 0.4188 0.4918 0.064 Uiso calc R 1 H
H6B 0.7259 0.3646 0.5285 0.064 Uiso calc R 1 H
H6C 0.7104 0.5037 0.5137 0.064 Uiso calc R 1 H
C7 0.57578(19) 0.28168(18) 0.33604(6) 0.0303(5) Uani d . 1 C
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
N2 0.0308(9) 0.0317(10) 0.0289(10) 0.0016(8) -0.0024(7) -0.0006(8)
C11 0.0408(11) 0.0298(11) 0.0344(11) -0.0058(10) 0.0053(9) -0.0014(9)
C12 0.0396(11) 0.0329(11) 0.0325(10) -0.0035(10) -0.0006(9) -0.0052(9)
C13 0.0361(11) 0.0421(12) 0.0266(10) 0.0094(10) 0.0035(9) 0.0019(9)
C14 0.0277(10) 0.0580(14) 0.0374(12) -0.0045(12) 0.0011(9) 0.0085(10)
C15 0.0309(11) 0.0550(14) 0.0383(12) -0.0042(11) -0.0056(9) -0.0016(10)
C16 0.0464(13) 0.0719(16) 0.0339(11) 0.0080(13) 0.0028(10) 0.0005(11)
O3 0.0408(9) 0.0291(8) 0.0589(9) -0.0029(8) -0.0084(8) 0.0080(8)
O1 0.0534(9) 0.0282(8) 0.0450(8) -0.0016(7) 0.0101(7) -0.0096(7)
O2 0.0594(9) 0.0297(7) 0.0279(7) -0.0094(7) -0.0016(7) 0.0009(6)
N1 0.0504(10) 0.0214(8) 0.0265(8) 0.0046(8) 0.0000(7) -0.0003(7)
C1 0.0482(12) 0.0279(10) 0.0309(10) 0.0079(10) -0.0002(9) 0.0014(9)
C2 0.0415(12) 0.0292(11) 0.0334(10) 0.0002(10) 0.0054(9) -0.0072(9)
C3 0.0352(11) 0.0431(13) 0.0287(10) -0.0004(11) 0.0011(9) -0.0019(10)
C4 0.0435(11) 0.0377(12) 0.0331(10) 0.0040(12) -0.0005(10) 0.0067(9)
C5 0.0492(12) 0.0287(11) 0.0349(10) -0.0015(11) 0.0012(10) 0.0039(9)
C6 0.0561(14) 0.0617(16) 0.0419(12) -0.0007(13) -0.0089(11) -0.0062(12)
C7 0.0241(10) 0.0333(12) 0.0334(11) -0.0070(10) 0.0006(8) -0.0024(10)
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'
O O 0.0106 0.0060 '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'
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
C15 N2 C11 112.24(15) y
N2 C11 C12 110.96(15) ?
C11 C12 C13 111.85(15) ?
C12 C13 C14 108.96(15) ?
C12 C13 C16 111.63(16) ?
C14 C13 C16 111.76(17) ?
C13 C14 C15 111.49(17) ?
N2 C15 C14 110.69(15) ?
C7 N1 C5 122.29(15) y
C7 N1 C1 122.91(14) y
C5 N1 C1 114.40(14) y
N1 C1 C2 110.83(15) ?
C1 C2 C3 112.68(15) ?
C4 C3 C2 109.51(14) ?
C4 C3 C6 111.85(16) ?
C2 C3 C6 111.39(16) ?
C5 C4 C3 112.27(15) ?
N1 C5 C4 110.90(16) ?
O1 C7 O2 124.23(17) y
O1 C7 N1 118.19(17) y
O2 C7 N1 117.58(16) y
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_publ_flag
N2 C15 1.483(2) y
N2 C11 1.488(2) y
C11 C12 1.515(2) ?
C12 C13 1.520(2) ?
C13 C14 1.521(3) ?
C13 C16 1.523(2) ?
C14 C15 1.525(2) ?
O1 C7 1.256(2) y
O2 C7 1.275(2) y
N1 C7 1.373(2) y
N1 C5 1.449(2) y
N1 C1 1.455(2) y
C1 C2 1.516(2) ?
C2 C3 1.523(2) ?
C3 C4 1.519(2) ?
C3 C6 1.528(2) ?
C4 C5 1.517(2) ?
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
O3 H1W O2 . 0.94(2) 1.79(2) 2.718(2) 172(2) y
O3 H2W O1 8_765 0.92(2) 1.79(2) 2.712(2) 177(2) y
N2 H1 O2 3_655 1.06(2) 1.63(2) 2.681(2) 167(2) y
N2 H2 O3 . 0.97(2) 1.84(2) 2.796(2) 172(2) y
C15 H15A O3 6_556 0.99 2.58 3.442(2) 146 y
C12 H12A O1 1_565 0.99 2.58 3.303(2) 129 y
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
C15 N2 C11 C12 55.8(2) y
N2 C11 C12 C13 -55.9(2) y
C11 C12 C13 C14 55.8(2) y
C11 C12 C13 C16 179.68(16) y
C12 C13 C14 C15 -55.9(2) y
C16 C13 C14 C15 -179.73(16) y
C11 N2 C15 C14 -55.9(2) y
C13 C14 C15 N2 56.5(2) y
C7 N1 C1 C2 -131.71(17) y
C5 N1 C1 C2 55.4(2) y
N1 C1 C2 C3 -53.1(2) y
C1 C2 C3 C4 52.1(2) y
C1 C2 C3 C6 176.33(15) y
C2 C3 C4 C5 -52.5(2) y
C6 C3 C4 C5 -176.44(16) y
C7 N1 C5 C4 131.01(17) y
C1 N1 C5 C4 -56.0(2) y
C3 C4 C5 N1 54.3(2) y
C5 N1 C7 O1 -4.3(3) y
C1 N1 C7 O1 -176.63(17) ?
C5 N1 C7 O2 175.59(16) ?
C1 N1 C7 O2 3.2(3) ?