#------------------------------------------------------------------------------
#$Date: 2017-10-13 03:48:21 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201957 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/01/52/2015282.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_2015282
loop_
_publ_author_name
'Demir, Selcuk'
'Yilmaz, Veysel T.'
'Harrison, William T. A.'
_publ_section_title
;
 (3-Hydroxy-2-pyridylmethyl)dimethylammonium dihydrogenphosphate
;
_journal_coeditor_code           SQ3006
_journal_issue                   4
_journal_name_full               'Acta Crystallographica Section C'
_journal_page_first              o216
_journal_page_last               o218
_journal_paper_doi               10.1107/S0108270106005853
_journal_volume                  62
_journal_year                    2006
_chemical_formula_iupac          'C8 H13 N2 O +, H2 O4 P -'
_chemical_formula_moiety         'C8 H13 N2 O +, H2 O4 P -'
_chemical_formula_sum            'C8 H15 N2 O5 P'
_chemical_formula_weight         250.19
_chemical_name_systematic
;
(3-Hydroxy-2-pyridylmethyl)dimethylammonium dihydrogenphosphate
;
_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'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 109.3578(11)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   10.7601(2)
_cell_length_b                   11.9724(2)
_cell_length_c                   8.91220(10)
_cell_measurement_reflns_used    4901
_cell_measurement_temperature    120(2)
_cell_measurement_theta_max      27.48
_cell_measurement_theta_min      2.91
_cell_volume                     1083.20(3)
_computing_cell_refinement       'HKL Scalepack (Otwinowski & Minor ,1997)'
_computing_data_collection       'Collect (Nonius, 1998)'
_computing_data_reduction
'HKL Denzo (Otwinowski & Minor, 1997) and Scalepack'
_computing_molecular_graphics    'ORTEP3 (Farrugia, 1997)'
_computing_publication_material  SHELXL97
_computing_structure_refinement  'SHELXL97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 1997)'
_diffrn_ambient_temperature      120(2)
_diffrn_measured_fraction_theta_full 0.995
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measurement_device_type  'Nonius KappaCCD'
_diffrn_measurement_method       'ω and φ'
_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  0.0292
_diffrn_reflns_av_sigmaI/netI    0.0165
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_number            22984
_diffrn_reflns_theta_full        27.53
_diffrn_reflns_theta_max         27.53
_diffrn_reflns_theta_min         2.96
_diffrn_standards_decay_%        0
_diffrn_standards_interval_count 0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.263
_exptl_absorpt_correction_T_max  0.914
_exptl_absorpt_correction_T_min  0.914
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SADABS; Bruker, 2003)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.534
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       cube
_exptl_crystal_F_000             528
_exptl_crystal_size_max          0.35
_exptl_crystal_size_mid          0.35
_exptl_crystal_size_min          0.35
_refine_diff_density_max         0.315
_refine_diff_density_min         -0.391
_refine_ls_extinction_coef       0.034(2)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     SHELXL97
_refine_ls_goodness_of_fit_ref   1.054
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     160
_refine_ls_number_reflns         2481
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.054
_refine_ls_R_factor_all          0.0303
_refine_ls_R_factor_gt           0.0271
_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/[σ²(Fo²)+(0.0283P)²+0.7457P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0681
_refine_ls_wR_factor_ref         0.0702
_reflns_number_gt                2282
_reflns_number_total             2481
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            sq3006.cif
_cod_data_source_block           I
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               2015282
_cod_database_fobs_code          2015282
loop_
_symmetry_equiv_pos_as_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_refinement_flags
_atom_site_occupancy
P P1 0.16330(3) 0.71981(2) 0.04893(3) 0.00932(11) Uani d . 1
O O1 0.07862(8) 0.63731(7) 0.09668(10) 0.01391(19) Uani d . 1
O O2 0.27118(8) 0.77220(7) 0.18593(10) 0.0140(2) Uani d . 1
O O3 0.07854(9) 0.81843(7) -0.05028(11) 0.01291(19) Uani d . 1
H H1 0.0063(18) 0.8024(13) -0.103(2) 0.015 Uiso d . 1
O O4 0.22776(9) 0.65744(7) -0.06218(11) 0.0161(2) Uani d . 1
H H2 0.2383(16) 0.6904(14) -0.141(2) 0.019 Uiso d . 1
C C1 0.59183(12) 0.75960(10) 0.22578(14) 0.0122(2) Uani d . 1
C C2 0.54888(12) 0.65224(10) 0.17002(15) 0.0146(2) Uani d . 1
H H2A 0.4575 0.6351 0.1312 0.017 Uiso calc R 1
C C3 0.64144(12) 0.57163(10) 0.17232(15) 0.0149(3) Uani d . 1
H H3A 0.6146 0.4983 0.1345 0.018 Uiso calc R 1
C C4 0.77402(12) 0.59911(10) 0.23047(15) 0.0141(2) Uani d . 1
H H4A 0.8372 0.5434 0.2317 0.017 Uiso calc R 1
C C5 0.72734(12) 0.78147(10) 0.28192(14) 0.0108(2) Uani d . 1
C C6 0.78105(12) 0.89447(10) 0.34491(14) 0.0116(2) Uani d . 1
H H6A 0.8630 0.8842 0.4363 0.014 Uiso calc R 1
H H6B 0.7165 0.9329 0.3843 0.014 Uiso calc R 1
C C7 0.91019(12) 0.91808(10) 0.16085(15) 0.0149(3) Uani d . 1
H H7A 0.9909 0.9022 0.2496 0.022 Uiso calc R 1
H H7B 0.9298 0.9708 0.0876 0.022 Uiso calc R 1
H H7C 0.8757 0.8486 0.1043 0.022 Uiso calc R 1
C C8 0.68967(12) 1.00072(11) 0.09135(15) 0.0173(3) Uani d . 1
H H8A 0.7137 1.0513 0.0189 0.026 Uiso calc R 1
H H8B 0.6286 1.0387 0.1351 0.026 Uiso calc R 1
H H8C 0.6472 0.9339 0.0331 0.026 Uiso calc R 1
N N1 0.81642(10) 0.70141(9) 0.28498(12) 0.0124(2) Uani d . 1
N N2 0.81024(10) 0.96771(8) 0.22321(12) 0.0112(2) Uani d . 1
H H3 0.8478(15) 1.0340(13) 0.2821(18) 0.013 Uiso d . 1
O O5 0.50784(9) 0.84319(7) 0.22640(12) 0.0173(2) Uani d . 1
H H4 0.4285(18) 0.8154(14) 0.205(2) 0.021 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'
P P 0.1023 0.0942 '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
O1 P1 O2 114.83(5) y
O1 P1 O3 111.14(5) y
O2 P1 O3 106.81(5) y
O1 P1 O4 107.61(5) y
O2 P1 O4 108.91(5) y
O3 P1 O4 107.28(5) y
P1 O3 H1 115.3(12) ?
P1 O4 H2 120.8(11) ?
O5 C1 C2 122.65(11) ?
O5 C1 C5 118.63(11) ?
C2 C1 C5 118.72(11) ?
C3 C2 C1 118.97(11) ?
C3 C2 H2A 120.5 ?
C1 C2 H2A 120.5 ?
C2 C3 C4 119.14(11) ?
C2 C3 H3A 120.4 ?
C4 C3 H3A 120.4 ?
N1 C4 C3 122.46(11) ?
N1 C4 H4A 118.8 ?
C3 C4 H4A 118.8 ?
N1 C5 C1 121.53(11) ?
N1 C5 C6 116.66(10) ?
C1 C5 C6 121.80(11) ?
C5 C6 N2 113.62(9) ?
C5 C6 H6A 108.8 ?
N2 C6 H6A 108.8 ?
C5 C6 H6B 108.8 ?
N2 C6 H6B 108.8 ?
H6A C6 H6B 107.7 ?
N2 C7 H7A 109.5 ?
N2 C7 H7B 109.5 ?
H7A C7 H7B 109.5 ?
N2 C7 H7C 109.5 ?
H7A C7 H7C 109.5 ?
H7B C7 H7C 109.5 ?
N2 C8 H8A 109.5 ?
N2 C8 H8B 109.5 ?
H8A C8 H8B 109.5 ?
N2 C8 H8C 109.5 ?
H8A C8 H8C 109.5 ?
H8B C8 H8C 109.5 ?
C4 N1 C5 119.18(10) ?
C8 N2 C7 111.12(10) ?
C8 N2 C6 112.85(9) ?
C7 N2 C6 112.67(9) ?
C8 N2 H3 108.1(9) ?
C7 N2 H3 107.9(9) ?
C6 N2 H3 103.7(9) ?
C1 O5 H4 108.9(11) ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_publ_flag
P1 O1 1.4980(9) y
P1 O2 1.5139(9) y
P1 O3 1.5726(9) y
P1 O4 1.5731(9) y
O3 H1 0.787(18) ?
O4 H2 0.848(18) ?
C1 O5 1.3497(15) ?
C1 C2 1.4001(17) ?
C1 C5 1.4005(17) ?
C2 C3 1.3822(17) ?
C2 H2A 0.9500 ?
C3 C4 1.3863(17) ?
C3 H3A 0.9500 ?
C4 N1 1.3406(16) ?
C4 H4A 0.9500 ?
C5 N1 1.3493(15) ?
C5 C6 1.5048(16) ?
C6 N2 1.5066(15) ?
C6 H6A 0.9900 ?
C6 H6B 0.9900 ?
C7 N2 1.4882(15) ?
C7 H7A 0.9800 ?
C7 H7B 0.9800 ?
C7 H7C 0.9800 ?
C8 N2 1.4865(15) ?
C8 H8A 0.9800 ?
C8 H8B 0.9800 ?
C8 H8C 0.9800 ?
N2 H3 0.963(15) ?
O5 H4 0.877(18) ?
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
O3 H1 N1 4_475 0.787(18) 1.955(18) 2.7243(14) 166(2)
O4 H2 O2 4_575 0.848(18) 1.749(18) 2.5813(13) 167(2)
N2 H3 O1 2_655 0.963(15) 1.661(16) 2.6187(13) 173.0(10)
O5 H4 O2 . 0.877(18) 1.723(18) 2.5939(12) 172(2)
C6 H6A O1 4_676 0.99 2.30 3.2663(15) 165
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
O5 C1 C2 C3 179.47(11)
C5 C1 C2 C3 0.03(18)
C1 C2 C3 C4 0.34(18)
C2 C3 C4 N1 0.02(19)
O5 C1 C5 N1 179.75(11)
C2 C1 C5 N1 -0.79(18)
O5 C1 C5 C6 1.04(17)
C2 C1 C5 C6 -179.50(11)
N1 C5 C6 N2 85.24(13)
C1 C5 C6 N2 -95.99(13)
C3 C4 N1 C5 -0.77(18)
C1 C5 N1 C4 1.15(17)
C6 C5 N1 C4 179.93(10)
C5 C6 N2 C8 66.40(13)
C5 C6 N2 C7 -60.45(13)
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 21133575
