#------------------------------------------------------------------------------
#$Date: 2016-02-19 16:29:56 +0200 (Fri, 19 Feb 2016) $
#$Revision: 176759 $
#$URL: svn://www.crystallography.net/cod/cif/2/00/63/2006319.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_2006319
loop_
_publ_author_name
'Ng, Seik Weng'
_publ_section_title
;
 Bis(dicyclohexylammonium) 2,6-Pyridinedicarboxylate Dihydrate
;
_journal_issue                   7
_journal_name_full               'Acta Crystallographica Section C'
_journal_page_first              986
_journal_page_last               987
_journal_paper_doi               10.1107/S010827019700293X
_journal_volume                  53
_journal_year                    1997
_chemical_formula_iupac          '2C12 H24 N + , C7 H3 N O4 2- , 2H2 O'
_chemical_formula_moiety         '2[C~12~H~24~N] [C~7~H3~NO~4~] 2OH~2~'
_chemical_formula_sum            'C31 H55 N3 O6'
_chemical_formula_weight         565.78
_chemical_name_systematic
;
 Bis(dicyclohexylammonium) 2,6-pyridinedicarboxylate dihydrate
;
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2yn'
_symmetry_space_group_name_H-M   'P 1 21/n 1'
_audit_creation_method           SHELXL
_cell_angle_alpha                90.00
_cell_angle_beta                 106.044(6)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   10.5790(10)
_cell_length_b                   18.1356(9)
_cell_length_c                   17.507(2)
_cell_measurement_reflns_used    25
_cell_measurement_temperature    298(2)
_cell_measurement_theta_max      11
_cell_measurement_theta_min      10
_cell_volume                     3228.0(5)
_computing_cell_refinement       'CAD4-VAX/PC (Enraf-Nonius Delft, 1988)'
_computing_data_collection       'CAD4-VAX/PC (Enraf-Nonius Delft, 1988)'
_computing_data_reduction
'NRCVAX (Gabe, Le Page, Charland, Lee & White, 1989)'
_computing_molecular_graphics    'ZORTEP (Zsolnai & Pritzkow, 1996)'
_computing_publication_material  SHELXL93
_computing_structure_refinement  'SHELXL93 (Sheldrick, 1993)'
_computing_structure_solution    'SHELXS86 (Sheldrick, 1990)'
_diffrn_ambient_temperature      298(2)
_diffrn_measurement_device       'Enraf-Nonius CAD4'
_diffrn_measurement_method       ω-scans
_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  0.0181
_diffrn_reflns_av_sigmaI/netI    0.0387
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       21
_diffrn_reflns_limit_k_min       0
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       0
_diffrn_reflns_number            5858
_diffrn_reflns_theta_max         24.97
_diffrn_reflns_theta_min         1.65
_diffrn_standards_decay_%        none
_diffrn_standards_interval_time  60
_diffrn_standards_number         3
_exptl_absorpt_coefficient_mu    0.080
_exptl_absorpt_correction_T_max  0.958
_exptl_absorpt_correction_T_min  0.922
_exptl_absorpt_correction_type   '\y-scan (North, Phillips & Mathews, 1968)'
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.164
_exptl_crystal_density_meas      ?
_exptl_crystal_description       'irregular block'
_exptl_crystal_F_000             1240
_exptl_crystal_size_max          0.53
_exptl_crystal_size_mid          0.53
_exptl_crystal_size_min          0.53
_refine_diff_density_max         0.370
_refine_diff_density_min         -0.267
_refine_ls_extinction_coef       'not refined'
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_all   1.107
_refine_ls_goodness_of_fit_obs   1.317
_refine_ls_hydrogen_treatment
;H atoms: riding model with U(H) = 1.5U~eq~(C,N); water H-atoms were
 calculated, U = 0.10 \%A^2^
;
_refine_ls_matrix_type           full
_refine_ls_number_parameters     370
_refine_ls_number_reflns         5664
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.107
_refine_ls_restrained_S_obs      1.317
_refine_ls_R_factor_all          0.1082
_refine_ls_R_factor_obs          .0672
_refine_ls_shift/esd_max         0.000
_refine_ls_shift/esd_mean        0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.1P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_all         0.1953
_refine_ls_wR_factor_obs         .1748
_reflns_number_observed          3326
_reflns_number_total             5664
_reflns_observed_criterion       >2sigma(I)
_cod_data_source_file            kh1129.cif
_cod_data_source_block           ipt156
_cod_depositor_comments
;
The following automatic conversions were performed:
'_symmetry_cell_setting' value 'Monoclinic' changed to 'monoclinic'
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_enum 1527 2010-12-29 10:47:43Z saulius 

The following automatic conversions were performed:

'_symmetry_cell_setting' value 'Monoclinic' changed to 'monoclinic'
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 

The following automatic conversions were performed:

'_exptl_crystal_density_meas' value 'not measured' was changed to '?'
- the value is perceived as not measured.

Automatic conversion script
Id: cif_fix_values 3008 2015-01-20 13:52:24Z robertas 

The following automatic conversions were performed:

'_refine_ls_weighting_scheme' value 'calc
w=1/[\s^2^(Fo^2^)+(0.1P)^2^] where P=(Fo^2^+2Fc^2^)/3' was changed to
'calc'. New tag '_refine_ls_weighting_details' was created. The value
of the new tag was set to 'w=1/[\s^2^(Fo^2^)+(0.1P)^2^] where
P=(Fo^2^+2Fc^2^)/3'.

Automatic conversion script
Id: cif_fix_values 3143 2015-03-26 13:38:13Z robertas 
;
_cod_original_cell_volume        3228.1(6)
_cod_original_sg_symbol_H-M      'P 21/n'
_cod_database_code               2006319
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -y-1/2, z-1/2'
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_disorder_group
_atom_site_type_symbol
O1 .5831(2) .20820(10) -.22720(10) .0643(6) Uani d . 1 . O
O2 .7142(2) .1375(2) -.1400(2) .142(2) Uani d . 1 . O
O3 .1320(2) .21090(10) -.25160(10) .0634(6) Uani d . 1 . O
O4 .0524(2) .18320(10) -.15190(10) .0676(6) Uani d . 1 . O
O5 -.0546(6) .0927(4) -.0577(4) .107(2) Uani d P .50 . O
H51 -.0256 .1109 -.1023 .100 Uiso d P .50 . H
H52 -.1160 .1289 -.0448 .100 Uiso d P .50 . H
O5' -.0579(5) .1599(5) -.0314(3) .110(2) Uani d P .50 . O
H51' -.0351 .1877 -.0733 .100 Uiso d P .50 . H
H52' -.1131 .1888 -.0048 .100 Uiso d P .50 . H
O6 .1419(4) .0551(3) .0688(2) .184(2) Uani d . 1 . O
H61 .0732 .0748 .0227 .100 Uiso d . 1 . H
H62 .1200 .0018 .0704 .100 Uiso d . 1 . H
N1 .8224(2) .24510(10) -.26540(10) .0443(5) Uani d . 1 . N
H1A .8963(2) .22810(10) -.23080(10) .066 Uiso calc R 1 . H
H1B .7541(2) .22970(10) -.24830(10) .066 Uiso calc R 1 . H
N2 .3280(2) .25800(10) -.31230(10) .0489(6) Uani d . 1 . N
H2A .2765(2) .23680(10) -.28540(10) .073 Uiso calc R 1 . H
H2B .4115(2) .24560(10) -.28710(10) .073 Uiso calc R 1 . H
N3 .3765(2) .17110(10) -.16980(10) .0442(5) Uani d . 1 . N
C1 .8256(2) .32760(10) -.2624(2) .0467(6) Uani d . 1 . C
H1 .7404(2) .34630(10) -.2943(2) .070 Uiso calc R 1 . H
C2 .8445(3) .3511(2) -.1771(2) .0682(9) Uani d . 1 . C
H2C .9263(3) .3309(2) -.1441(2) .102 Uiso calc R 1 . H
H2D .7732(3) .3318(2) -.1581(2) .102 Uiso calc R 1 . H
C3 .8476(4) .4351(2) -.1703(2) .0840(10) Uani d . 1 . C
H3A .7628(4) .4549(2) -.1993(2) .126 Uiso calc R 1 . H
H3B .8639(4) .4490(2) -.1149(2) .126 Uiso calc R 1 . H
C4 .9538(4) .4677(2) -.2031(2) .0790(10) Uani d . 1 . C
H4A .9499(4) .5211(2) -.2012(2) .119 Uiso calc R 1 . H
H4B 1.0395(4) .4523(2) -.1704(2) .119 Uiso calc R 1 . H
C5 .9367(3) .4433(2) -.2874(2) .0713(9) Uani d . 1 . C
H5A 1.0090(3) .4621(2) -.3058(2) .107 Uiso calc R 1 . H
H5B .8558(3) .4640(2) -.3211(2) .107 Uiso calc R 1 . H
C6 .9320(3) .3593(2) -.2953(2) .0589(8) Uani d . 1 . C
H6A .9148(3) .3458(2) -.3509(2) .088 Uiso calc R 1 . H
H6B 1.0165(3) .3388(2) -.2668(2) .088 Uiso calc R 1 . H
C7 .8110(2) .21010(10) -.3444(2) .0472(6) Uani d . 1 . C
H7 .8878(2) .22490(10) -.3618(2) .071 Uiso calc R 1 . H
C8 .8146(3) .1276(2) -.3351(2) .0608(8) Uani d . 1 . C
H8A .7401(3) .1115(2) -.3172(2) .091 Uiso calc R 1 . H
H8B .8945(3) .1132(2) -.2954(2) .091 Uiso calc R 1 . H
C9 .8099(4) .0911(2) -.4143(2) .0780(10) Uani d . 1 . C
H9A .8881(4) .1043(2) -.4298(2) .117 Uiso calc R 1 . H
H9B .8094(4) .0379(2) -.4081(2) .117 Uiso calc R 1 . H
C10 .6899(5) .1142(2) -.4784(2) .0970(10) Uani d . 1 . C
H10A .6114(5) .0969(2) -.4656(2) .145 Uiso calc R 1 . H
H10B .6919(5) .0923(2) -.5286(2) .145 Uiso calc R 1 . H
C11 .6852(5) .1977(2) -.4862(2) .107(2) Uani d . 1 . C
H11A .6050(5) .2121(2) -.5257(2) .160 Uiso calc R 1 . H
H11B .7592(5) .2144(2) -.5043(2) .160 Uiso calc R 1 . H
C12 .6901(3) .2347(2) -.4066(2) .0713(9) Uani d . 1 . C
H12A .6912(3) .2878(2) -.4123(2) .107 Uiso calc R 1 . H
H12B .6123(3) .2215(2) -.3905(2) .107 Uiso calc R 1 . H
C13 .3160(3) .3395(2) -.3050(2) .0598(8) Uani d . 1 . C
H13 .2237(3) .3527(2) -.3290(2) .090 Uiso calc R 1 . H
C14 .3492(4) .3589(2) -.2177(2) .0850(10) Uani d . 1 . C
H14A .4388(4) .3440(2) -.1918(2) .128 Uiso calc R 1 . H
H14B .2912(4) .3322(2) -.1932(2) .128 Uiso calc R 1 . H
C15 .3349(4) .4416(2) -.2057(3) .1080(10) Uani d . 1 . C
H15A .2434(4) .4557(2) -.2265(3) .161 Uiso calc R 1 . H
H15B .3619(4) .4528(2) -.1493(3) .161 Uiso calc R 1 . H
C16 .4154(5) .4841(2) -.2460(4) .126(2) Uani d . 1 . C
H16A .5077(5) .4745(2) -.2207(4) .190 Uiso calc R 1 . H
H16B .3998(5) .5363(2) -.2407(4) .190 Uiso calc R 1 . H
C17 .3848(7) .4649(2) -.3328(4) .150(2) Uani d . 1 . C
H17A .4447(7) .4914(2) -.3561(4) .225 Uiso calc R 1 . H
H17B .2962(7) .4810(2) -.3594(4) .225 Uiso calc R 1 . H
C18 .3964(5) .3810(2) -.3474(3) .110(2) Uani d . 1 . C
H18A .3660(5) .3706(2) -.4039(3) .166 Uiso calc R 1 . H
H18B .4877(5) .3657(2) -.3284(3) .166 Uiso calc R 1 . H
C19 .2950(3) .2233(2) -.3932(2) .0538(7) Uani d . 1 . C
H19 .3486(3) .2463(2) -.4242(2) .081 Uiso calc R 1 . H
C20 .3290(3) .1424(2) -.3829(2) .0686(9) Uani d . 1 . C
H20A .2807(3) .1198(2) -.3493(2) .103 Uiso calc R 1 . H
H20B .4222(3) .1368(2) -.3571(2) .103 Uiso calc R 1 . H
C21 .2946(4) .1039(2) -.4632(2) .0890(10) Uani d . 1 . C
H21A .3484(4) .1238(2) -.4951(2) .133 Uiso calc R 1 . H
H21B .3136(4) .0517(2) -.4555(2) .133 Uiso calc R 1 . H
C22 .1504(4) .1145(2) -.5065(2) .0930(10) Uani d . 1 . C
H22A .1316(4) .0917(2) -.5586(2) .139 Uiso calc R 1 . H
H22B .0967(4) .0904(2) -.4770(2) .139 Uiso calc R 1 . H
C23 .1161(4) .1944(2) -.5156(2) .0920(10) Uani d . 1 . C
H23A .0226(4) .1995(2) -.5409(2) .138 Uiso calc R 1 . H
H23B .1629(4) .2171(2) -.5499(2) .138 Uiso calc R 1 . H
C24 .1506(3) .2342(2) -.4363(2) .0706(9) Uani d . 1 . C
H24A .0969(3) .2153(2) -.4039(2) .106 Uiso calc R 1 . H
H24B .1323(3) .2864(2) -.4449(2) .106 Uiso calc R 1 . H
C25 .6069(3) .1650(2) -.1696(2) .0653(9) Uani d . 1 . C
C26 .4967(2) .1459(2) -.1330(2) .0479(7) Uani d . 1 . C
C27 .5216(3) .1055(2) -.0632(2) .0556(7) Uani d . 1 . C
H27 .6052(3) .0869(2) -.0396(2) .083 Uiso calc R 1 . H
C28 .4211(3) .0934(2) -.0294(2) .0561(7) Uani d . 1 . C
H28 .4361(3) .0670(2) .0178(2) .084 Uiso calc R 1 . H
C29 .2975(3) .1207(2) -.0660(2) .0518(7) Uani d . 1 . C
H29 .2286(3) .1142(2) -.0433(2) .078 Uiso calc R 1 . H
C30 .2782(2) .15800(10) -.1372(2) .0408(6) Uani d . 1 . C
C31 .1433(2) .1863(2) -.1842(2) .0455(6) Uani d . 1 . C
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'
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
C1 N1 C7 116.8(2) yes
C13 N2 C19 119.6(2) yes
C26 N3 C30 118.7(2) yes
N1 C1 C2 108.2(2) yes
N1 C1 C6 112.2(2) yes
C2 C1 C6 111.1(2) ?
C1 C2 C3 110.6(3) ?
C2 C3 C4 111.2(3) ?
C3 C4 C5 110.9(3) ?
C4 C5 C6 112.0(3) ?
C1 C6 C5 110.7(2) ?
N1 C7 C8 109.1(2) yes
N1 C7 C12 112.3(2) yes
C12 C7 C8 111.4(2) ?
C7 C8 C9 109.9(3) ?
C8 C9 C10 111.5(3) ?
C9 C10 C11 110.2(3) ?
C10 C11 C12 111.2(3) ?
C7 C12 C11 109.7(3) ?
N2 C13 C14 108.5(2) yes
N2 C13 C18 112.7(3) yes
C18 C13 C14 112.6(3) ?
C13 C14 C15 111.4(3) ?
C14 C15 C16 110.9(4) ?
C15 C16 C17 111.9(4) ?
C16 C17 C18 112.9(4) ?
C13 C18 C17 109.4(3) ?
N2 C19 C20 108.1(2) yes
N2 C19 C24 110.8(2) yes
C20 C19 C24 111.1(3) ?
C19 C20 C21 110.4(3) ?
C20 C21 C22 110.8(3) ?
C21 C22 C23 110.9(3) ?
C22 C23 C24 112.0(3) ?
C23 C24 C19 110.4(3) ?
O1 C25 O2 124.0(3) yes
O1 C25 C26 118.6(3) yes
O2 C25 C26 117.5(3) yes
N3 C26 C25 117.2(2) yes
N3 C26 C27 122.0(2) yes
C25 C26 C27 120.8(2) ?
C26 C27 C28 119.0(3) ?
C27 C28 C29 119.4(3) ?
C28 C29 C30 118.6(3) ?
N3 C30 C29 122.2(2) yes
N3 C30 C31 115.5(2) yes
C29 C30 C31 122.3(2) ?
O3 C31 O4 124.6(2) yes
O3 C31 C30 117.8(2) yes
O4 C31 C30 117.7(2) yes
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_site_symmetry_2
_geom_bond_distance
_geom_bond_publ_flag
O1 C25 . 1.246(4) yes
O2 C25 . 1.217(4) yes
O3 C31 . 1.235(3) yes
O4 C31 . 1.245(3) yes
N1 C1 . 1.499(3) yes
N1 C7 . 1.496(3) yes
N2 C13 . 1.493(3) yes
N2 C19 . 1.499(3) yes
N3 C26 . 1.337(3) yes
N3 C30 . 1.339(3) yes
C1 C2 . 1.511(4) ?
C1 C6 . 1.513(4) ?
C2 C3 . 1.528(4) ?
C3 C4 . 1.516(5) ?
C4 C5 . 1.503(4) ?
C5 C6 . 1.529(4) ?
C7 C8 . 1.505(4) ?
C7 C12 . 1.500(4) ?
C8 C9 . 1.524(4) ?
C9 C10 . 1.504(5) ?
C10 C11 . 1.519(5) ?
C11 C12 . 1.536(5) ?
C13 C14 . 1.511(5) ?
C13 C18 . 1.481(5) ?
C14 C15 . 1.527(5) ?
C15 C16 . 1.467(6) ?
C16 C17 . 1.504(7) ?
C17 C18 . 1.553(6) ?
C19 C20 . 1.508(4) ?
C19 C24 . 1.518(4) ?
C20 C21 . 1.521(4) ?
C21 C22 . 1.517(5) ?
C22 C23 . 1.491(5) ?
C23 C24 . 1.517(4) ?
C25 C26 . 1.518(4) ?
C26 C27 . 1.386(4) ?
C27 C28 . 1.368(4) ?
C28 C29 . 1.380(4) ?
C29 C30 . 1.382(4) ?
C30 C31 . 1.526(3) ?
N1 O1 . 2.871(3) yes
N1 O4 1_655 2.908(3) yes
N2 O1 . 2.846(3) yes
N2 O3 . 2.717(3) yes
O5 O2 1_455 2.602(6) yes
O5 O4 . 2.778(6) yes
O5 O6 . 2.674(7) yes
O5' O2 1_455 2.656(6) yes
O5' O4 . 2.710(5) yes
O6 O5 3_555 2.825(9) yes
