#------------------------------------------------------------------------------
#$Date: 2016-02-20 02:53:41 +0200 (Sat, 20 Feb 2016) $
#$Revision: 176768 $
#$URL: svn://www.crystallography.net/cod/cif/2/10/56/2105690.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_2105690
loop_
_publ_author_name
'Clegg, William'
'Tooke, Duncan M.'
_publ_section_title
;
 Alkali metal complexes of 6-methyl-2-pyridone: simple formulae, but not
 so simple structures
;
_journal_coeditor_code           PS5030
_journal_issue                   6
_journal_name_full               'Acta Crystallographica Section B'
_journal_page_first              603
_journal_page_last               612
_journal_paper_doi               10.1107/S2052519213025980
_journal_volume                  69
_journal_year                    2013
_chemical_formula_moiety         'Na +,C6 H6 N O -,2 H2 O'
_chemical_formula_sum            'C6 H10 N Na O3'
_chemical_formula_weight         167.14
_chemical_name_systematic
;
 ?
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2ybc'
_space_group_name_H-M_alt        'P 1 21/c 1'
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 1 21/c 1'
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-2013
_cell_angle_alpha                90
_cell_angle_beta                 92.8320(13)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   13.8784(15)
_cell_length_b                   8.3444(9)
_cell_length_c                   6.9228(7)
_cell_measurement_reflns_used    3850
_cell_measurement_temperature    160(2)
_cell_measurement_theta_max      28.15
_cell_measurement_theta_min      2.44
_cell_volume                     800.73(15)
_computing_cell_refinement       'Bruker APEX2'
_computing_data_collection       'Bruker SMART'
_computing_data_reduction        'Bruker APEX2'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL and local programs'
_computing_structure_refinement  SHELXL-2013
_computing_structure_solution    'Bruker SHELXTL'
_diffrn_ambient_temperature      160(2)
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.982
_diffrn_measurement_device_type  'Bruker SMART 1K CCD diffractometer'
_diffrn_measurement_method       'thin-slice ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0206
_diffrn_reflns_limit_h_max       18
_diffrn_reflns_limit_h_min       -18
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       9
_diffrn_reflns_limit_l_min       -9
_diffrn_reflns_number            6593
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         28.290
_diffrn_reflns_theta_min         2.849
_exptl_absorpt_coefficient_mu    0.154
_exptl_absorpt_correction_T_max  0.942
_exptl_absorpt_correction_T_min  0.810
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   SADABS
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.386
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             352
_exptl_crystal_size_max          0.80
_exptl_crystal_size_mid          0.80
_exptl_crystal_size_min          0.05
_refine_diff_density_max         0.421
_refine_diff_density_min         -0.175
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.034
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     117
_refine_ls_number_reflns         1950
_refine_ls_number_restraints     4
_refine_ls_restrained_S_all      1.033
_refine_ls_R_factor_all          0.0406
_refine_ls_R_factor_gt           0.0340
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
;
 w=1/[σ²(Fo²)+(0.0549P)²+0.2218P]
 where P=(Fo²+2Fc²)/3
;
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0912
_refine_ls_wR_factor_ref         0.0956
_reflns_number_gt                1684
_reflns_number_total             1950
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            ps5030.cif
_cod_data_source_block           dmt34_1
_cod_database_code               2105690
#BEGIN Tags that were not found in dictionaries:
_shelx_space_group_comment
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_shelx_estimated_absorpt_t_min   0.887
_shelx_estimated_absorpt_t_max   0.992
_shelxl_version_number           20.13
#END Tags that were not found in dictionaries
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'
loop_
_atom_site_type_symbol
_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_occupancy
Na Na1 0.51314(4) 0.50189(6) 0.25045(7) 0.02154(15) Uani d 1
O O1 0.38878(6) 0.44159(11) 0.47268(12) 0.0214(2) Uani d 1
N N1 0.26454(7) 0.52877(11) 0.27246(14) 0.0170(2) Uani d 1
C C1 0.29655(8) 0.45057(13) 0.43520(15) 0.0153(2) Uani d 1
C C2 0.22908(9) 0.37894(15) 0.55688(17) 0.0215(3) Uani d 1
H H2 0.2506 0.3287 0.6743 0.026 Uiso calc 1
C C3 0.13281(9) 0.38312(15) 0.50318(19) 0.0253(3) Uani d 1
H H3 0.0875 0.3326 0.5816 0.030 Uiso calc 1
C C4 0.10108(9) 0.46142(16) 0.33346(19) 0.0236(3) Uani d 1
H H4 0.0345 0.4643 0.2946 0.028 Uiso calc 1
C C5 0.16881(9) 0.53453(15) 0.22350(17) 0.0205(3) Uani d 1
C C6 0.14139(11) 0.6258(2) 0.0418(2) 0.0373(4) Uani d 1
H H6A 0.1660 0.7356 0.0532 0.056 Uiso calc 1
H H6B 0.0710 0.6281 0.0226 0.056 Uiso calc 1
H H6C 0.1693 0.5730 -0.0689 0.056 Uiso calc 1
O O2 0.59557(6) 0.61178(11) -0.00336(12) 0.0216(2) Uani d 1
H H2A 0.6001(13) 0.7125(11) -0.003(3) 0.040(5) Uiso d 1
H H2B 0.6463(9) 0.582(2) -0.053(2) 0.041(5) Uiso d 1
O O3 0.41000(7) 0.74206(11) 0.18535(17) 0.0326(3) Uani d 1
H H3A 0.3994(19) 0.780(3) 0.076(2) 0.085(9) Uiso d 1
H H3B 0.3591(9) 0.693(2) 0.206(3) 0.047(5) Uiso d 1
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'
Na Na 0.0362 0.0249 '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_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle
O1 Na1 O1 . 3_666 85.73(3)
O1 Na1 O2 . . 162.25(4)
O1 Na1 O2 3_666 . 104.51(4)
O1 Na1 O2 3_666 3_665 167.03(4)
O1 Na1 O2 . 3_665 85.90(3)
O1 Na1 O3 . . 82.00(4)
O1 Na1 O3 3_666 2_645 78.43(4)
O1 Na1 O3 . 2_645 91.06(4)
O1 Na1 O3 3_666 . 106.94(4)
O1 Na1 H3B . . 66.8(3)
O1 Na1 H3B 3_666 . 113.8(4)
O2 Na1 O2 . 3_665 86.18(3)
O2 Na1 O3 . . 81.15(4)
O2 Na1 O3 . 2_645 105.05(4)
O2 Na1 O3 3_665 2_645 91.84(4)
O2 Na1 O3 3_665 . 81.65(4)
O2 Na1 H3B . . 95.6(3)
O2 Na1 H3B 3_665 . 71.6(4)
O3 Na1 O3 . 2_645 170.77(3)
O3 Na1 H3B . . 18.2(2)
O3 Na1 H3B 2_645 . 152.6(3)
Na1 O1 Na1 . 3_666 94.27(3)
Na1 O1 C1 . . 126.09(7)
Na1 O1 C1 3_666 . 132.87(7)
C1 N1 C5 . . 120.07(10)
O1 C1 N1 . . 118.26(10)
O1 C1 C2 . . 122.02(10)
N1 C1 C2 . . 119.71(10)
C1 C2 H2 . . 120.3
C1 C2 C3 . . 119.39(11)
H2 C2 C3 . . 120.3
C2 C3 H3 . . 119.9
C2 C3 C4 . . 120.21(11)
H3 C3 C4 . . 119.9
C3 C4 H4 . . 120.8
C3 C4 C5 . . 118.41(11)
H4 C4 C5 . . 120.8
N1 C5 C4 . . 122.14(11)
N1 C5 C6 . . 115.58(11)
C4 C5 C6 . . 122.28(11)
C5 C6 H6A . . 109.5
C5 C6 H6B . . 109.5
C5 C6 H6C . . 109.5
H6A C6 H6B . . 109.5
H6A C6 H6C . . 109.5
H6B C6 H6C . . 109.5
Na1 O2 Na1 . 3_665 93.82(3)
Na1 O2 H2A . . 115.5(13)
Na1 O2 H2A 3_665 . 115.8(13)
Na1 O2 H2B . . 130.3(13)
Na1 O2 H2B 3_665 . 95.9(13)
H2A O2 H2B . . 103.4(18)
Na1 O3 Na1 . 2_655 116.01(4)
Na1 O3 H3A . . 123(2)
Na1 O3 H3A 2_655 . 83(2)
Na1 O3 H3B . . 93.2(14)
Na1 O3 H3B 2_655 . 140.3(14)
H3A O3 H3B . . 103(2)
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
Na1 Na1 3_665 3.4689(10) ?
Na1 Na1 3_666 3.4924(10) ?
Na1 Na1 2_655 4.1881(5) ?
Na1 Na1 2_645 4.1881(5) ?
Na1 O1 . 2.4210(10) y
Na1 O1 3_666 2.3433(10) y
Na1 O2 . 2.3313(10) y
Na1 O2 3_665 2.4180(10) y
Na1 O3 . 2.4909(11) y
Na1 O3 2_645 2.4472(11) y
Na1 H3B . 2.671(19) ?
O1 Na1 3_666 2.3433(10) ?
O1 C1 . 1.2956(14) ?
N1 C1 . 1.3575(14) ?
N1 C5 . 1.3556(15) ?
C1 C2 . 1.4218(15) ?
C2 H2 . 0.950 ?
C2 C3 . 1.3695(17) ?
C3 H3 . 0.950 ?
C3 C4 . 1.3964(19) ?
C4 H4 . 0.950 ?
C4 C5 . 1.3806(18) ?
C5 C6 . 1.5031(18) ?
C6 H6A . 0.980 ?
C6 H6B . 0.980 ?
C6 H6C . 0.980 ?
O2 Na1 3_665 2.4180(10) ?
O2 H2A . 0.842(9) ?
O2 H2B . 0.836(9) ?
O3 Na1 2_655 2.4473(11) ?
O3 H3A . 0.828(10) ?
O3 H3B . 0.836(9) ?
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
O2 H2A O1 2_655 0.842(9) 1.929(10) 2.7680(13) 173.8(19) y
O2 H2B N1 3_665 0.836(9) 2.209(11) 2.9955(13) 156.6(17) y
O3 H3A O1 4_575 0.828(10) 2.43(2) 3.0298(13) 130(2) y
O3 H3B N1 . 0.836(9) 1.966(11) 2.7798(14) 164(2) y
