#------------------------------------------------------------------------------
#$Date: 2016-02-20 18:35:30 +0200 (Sat, 20 Feb 2016) $
#$Revision: 176787 $
#$URL: svn://www.crystallography.net/cod/cif/2/21/86/2218633.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_2218633
loop_
_publ_author_name
'Li, Ming-Xia'
'Zhu, Miao-Li'
'Lu, Li-Ping'
_publ_section_title
;
 Ethyl [(2-hydroxyphenyl)(pyridinium-2-ylamino)methyl]phosphonate
 methanol solvate
;
_journal_coeditor_code           CF2201
_journal_issue                   7
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o1178
_journal_page_last               o1179
_journal_paper_doi               10.1107/S1600536808015675
_journal_volume                  64
_journal_year                    2008
_chemical_formula_iupac          'C14 H17 N2 O4 P , C H4 O'
_chemical_formula_moiety         'C14 H17 N2 O4 P , C H4 O'
_chemical_formula_sum            'C15 H21 N2 O5 P'
_chemical_formula_weight         340.31
_chemical_name_systematic
;
Ethyl [(2-hydroxyphenyl)(pyridinium-2-ylamino)methyl]phosphonate
methanol solvate
;
_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           SHELXL97
_cell_angle_alpha                90.00
_cell_angle_beta                 122.308(14)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   12.821(3)
_cell_length_b                   9.536(2)
_cell_length_c                   16.567(3)
_cell_measurement_reflns_used    1906
_cell_measurement_temperature    298(2)
_cell_measurement_theta_max      23.8
_cell_measurement_theta_min      2.48
_cell_volume                     1711.9(7)
_computing_cell_refinement       'SAINT (Bruker, 2000)'
_computing_data_collection       'SMART (Bruker, 2000)'
_computing_data_reduction        'SAINT (Bruker, 2000)'
_computing_molecular_graphics    'SHELXTL/PC (Sheldrick, 2008)'
_computing_publication_material
'PLATON (Spek, 2003) and publCIF (Westrip, 2008)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      298(2)
_diffrn_measured_fraction_theta_full 0.991
_diffrn_measured_fraction_theta_max 0.991
_diffrn_measurement_device_type  'Bruker SMART 1K CCD'
_diffrn_measurement_method       ω
_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  0.0336
_diffrn_reflns_av_sigmaI/netI    0.0447
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            6784
_diffrn_reflns_theta_full        25.00
_diffrn_reflns_theta_max         25.00
_diffrn_reflns_theta_min         1.88
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.186
_exptl_absorpt_correction_T_max  0.964
_exptl_absorpt_correction_T_min  0.875
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SADABS; Sheldrick, 2000)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.320
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             720
_exptl_crystal_size_max          0.40
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.20
_refine_diff_density_max         0.337
_refine_diff_density_min         -0.343
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.138
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     210
_refine_ls_number_reflns         2991
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.143
_refine_ls_R_factor_all          0.0836
_refine_ls_R_factor_gt           0.0669
_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)+(0.052P)²+1.1778P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1403
_refine_ls_wR_factor_ref         0.1471
_reflns_number_gt                2419
_reflns_number_total             2991
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            cf2201.cif
_cod_data_source_block           I
_cod_original_cell_volume        1711.9(6)
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               2218633
_cod_database_fobs_code          2218633
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 0.75798(7) 0.45914(9) 0.40161(6) 0.0359(3) Uani d . 1
O O1 0.5572(2) 0.7872(3) 0.22842(16) 0.0561(7) Uani d . 1
H H1 0.5007 0.8424 0.1964 0.067 Uiso d R 1
O O2 0.7741(2) 0.3583(3) 0.33273(18) 0.0578(7) Uani d . 1
O O3 0.86639(19) 0.4487(2) 0.50109(15) 0.0466(6) Uani d . 1
O O4 0.63500(19) 0.4400(2) 0.38884(15) 0.0481(6) Uani d . 1
N N1 0.8906(2) 0.6464(3) 0.37455(17) 0.0390(7) Uani d . 1
H H1A 0.9521 0.6023 0.4221 0.047 Uiso d R 1
N N2 1.0392(2) 0.7331(3) 0.35182(17) 0.0381(6) Uani d . 1
H H2A 1.0852 0.6775 0.3996 0.046 Uiso d R 1
C C1 0.6172(3) 0.8248(3) 0.3218(2) 0.0417(8) Uani d . 1
C C2 0.5805(3) 0.9373(4) 0.3538(3) 0.0552(10) Uani d . 1
H H2 0.5115 0.9893 0.3105 0.066 Uiso calc R 1
C C3 0.6448(4) 0.9723(4) 0.4481(3) 0.0681(12) Uani d . 1
H H3 0.6190 1.0475 0.4690 0.082 Uiso calc R 1
C C4 0.7468(4) 0.8976(5) 0.5121(3) 0.0713(12) Uani d . 1
H H4 0.7905 0.9215 0.5765 0.086 Uiso calc R 1
C C5 0.7848(3) 0.7865(4) 0.4808(2) 0.0545(10) Uani d . 1
H H5 0.8549 0.7364 0.5246 0.065 Uiso calc R 1
C C6 0.7210(3) 0.7479(3) 0.3857(2) 0.0373(7) Uani d . 1
C C7 0.7639(3) 0.6274(3) 0.3523(2) 0.0352(7) Uani d . 1
H H7 0.7091 0.6217 0.2827 0.042 Uiso calc R 1
C C8 0.9195(3) 0.7286(3) 0.3241(2) 0.0336(7) Uani d . 1
C C9 0.8361(3) 0.8096(3) 0.2451(2) 0.0415(8) Uani d . 1
H H9 0.7530 0.8119 0.2249 0.050 Uiso calc R 1
C C10 0.8774(3) 0.8845(4) 0.1985(2) 0.0531(10) Uani d . 1
H H10 0.8219 0.9379 0.1457 0.064 Uiso calc R 1
C C11 1.0008(4) 0.8832(4) 0.2277(3) 0.0559(10) Uani d . 1
H H11 1.0282 0.9341 0.1946 0.067 Uiso calc R 1
C C12 1.0803(3) 0.8069(4) 0.3050(3) 0.0479(9) Uani d . 1
H H12 1.1637 0.8051 0.3260 0.057 Uiso calc R 1
C C13 0.7568(5) 0.2100(5) 0.3340(4) 0.0900(15) Uani d D 1
H H13A 0.7122 0.1760 0.2687 0.108 Uiso calc R 1
H H13B 0.7055 0.1931 0.3598 0.108 Uiso calc R 1
C C14 0.8694(6) 0.1287(6) 0.3889(5) 0.126(2) Uani d D 1
H H14A 0.9171 0.1363 0.3600 0.189 Uiso calc R 1
H H14B 0.8489 0.0322 0.3899 0.189 Uiso calc R 1
H H14C 0.9165 0.1640 0.4530 0.189 Uiso calc R 1
O O5 0.6628(3) 0.3431(4) 0.5586(2) 0.0890(10) Uani d . 1
H H5A 0.6514 0.3728 0.5080 0.107 Uiso d R 1
C C15 0.5492(6) 0.3157(8) 0.5475(5) 0.125(2) Uani d . 1
H H15A 0.4896 0.2940 0.4818 0.187 Uiso calc R 1
H H15B 0.5226 0.3967 0.5661 0.187 Uiso calc R 1
H H15C 0.5571 0.2375 0.5868 0.187 Uiso calc R 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
O4 P1 O3 116.22(13)
O4 P1 O2 111.04(14)
O3 P1 O2 110.63(14)
O4 P1 C7 109.88(14)
O3 P1 C7 108.56(13)
O2 P1 C7 99.12(14)
C1 O1 H1 109.5
C13 O2 P1 120.4(3)
C8 N1 C7 123.6(2)
C8 N1 H1A 115.6
C7 N1 H1A 120.8
C8 N2 C12 123.1(3)
C8 N2 H2A 112.8
C12 N2 H2A 123.9
O1 C1 C2 122.6(3)
O1 C1 C6 117.3(3)
C2 C1 C6 120.1(3)
C3 C2 C1 120.5(4)
C3 C2 H2 119.7
C1 C2 H2 119.7
C2 C3 C4 120.2(4)
C2 C3 H3 119.9
C4 C3 H3 119.9
C3 C4 C5 119.7(4)
C3 C4 H4 120.2
C5 C4 H4 120.2
C4 C5 C6 121.4(4)
C4 C5 H5 119.3
C6 C5 H5 119.3
C5 C6 C1 118.1(3)
C5 C6 C7 120.9(3)
C1 C6 C7 120.9(3)
N1 C7 C6 112.7(3)
N1 C7 P1 107.5(2)
C6 C7 P1 113.4(2)
N1 C7 H7 107.7
C6 C7 H7 107.7
P1 C7 H7 107.7
N1 C8 N2 116.9(3)
N1 C8 C9 125.5(3)
N2 C8 C9 117.6(3)
C10 C9 C8 119.3(3)
C10 C9 H9 120.4
C8 C9 H9 120.4
C9 C10 C11 121.3(3)
C9 C10 H10 119.3
C11 C10 H10 119.3
C12 C11 C10 118.6(3)
C12 C11 H11 120.7
C10 C11 H11 120.7
N2 C12 C11 120.0(3)
N2 C12 H12 120.0
C11 C12 H12 120.0
O2 C13 C14 115.2(4)
O2 C13 H13A 108.5
C14 C13 H13A 108.5
O2 C13 H13B 108.5
C14 C13 H13B 108.5
H13A C13 H13B 107.5
C13 C14 H14A 109.5
C13 C14 H14B 109.5
H14A C14 H14B 109.5
C13 C14 H14C 109.5
H14A C14 H14C 109.5
H14B C14 H14C 109.5
C15 O5 H5A 109.1
O5 C15 H15A 109.5
O5 C15 H15B 109.5
H15A C15 H15B 109.5
O5 C15 H15C 109.5
H15A C15 H15C 109.5
H15B C15 H15C 109.5
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
P1 O4 1.486(2)
P1 O3 1.486(2)
P1 O2 1.588(3)
P1 C7 1.821(3)
O1 C1 1.357(4)
O1 H1 0.820
O2 C13 1.433(5)
N1 C8 1.334(4)
N1 C7 1.473(4)
N1 H1A 0.869
N2 C8 1.347(4)
N2 C12 1.347(4)
N2 H2A 0.870
C1 C2 1.385(5)
C1 C6 1.387(4)
C2 C3 1.363(5)
C2 H2 0.930
C3 C4 1.364(6)
C3 H3 0.930
C4 C5 1.378(5)
C4 H4 0.930
C5 C6 1.381(4)
C5 H5 0.930
C6 C7 1.502(4)
C7 H7 0.980
C8 C9 1.399(4)
C9 C10 1.351(4)
C9 H9 0.930
C10 C11 1.386(5)
C10 H10 0.930
C11 C12 1.347(5)
C11 H11 0.930
C12 H12 0.930
C13 C14 1.451(6)
C13 H13A 0.970
C13 H13B 0.970
C14 H14A 0.960
C14 H14B 0.960
C14 H14C 0.960
O5 C15 1.391(6)
O5 H5A 0.821
C15 H15A 0.960
C15 H15B 0.960
C15 H15C 0.960
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
N1 H1A O3 . 0.87 2.57 2.957(3) 108 y
N2 H2A O3 3_766 0.87 1.86 2.692(3) 160 y
N1 H1A O3 3_766 0.87 2.03 2.813(3) 150 y
O1 H1 O4 2_655 0.82 1.81 2.618(3) 170 y
C7 H7 O1 . 0.98 2.28 2.783(4) 111 y
C9 H9 O1 . 0.93 2.55 3.438(5) 160 y
C12 H12 O5 3_766 0.93 2.46 3.169(5) 133 y
O5 H5A O4 . 0.82 1.98 2.795(4) 176 y
C14 H14B Cg 1_545 0.96 2.91 3.697(8) 141 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
O4 P1 O2 C13 -55.0(3)
O3 P1 O2 C13 75.6(3)
C7 P1 O2 C13 -170.5(3)
O1 C1 C2 C3 -179.0(3)
C6 C1 C2 C3 -0.9(5)
C1 C2 C3 C4 0.6(6)
C2 C3 C4 C5 0.1(7)
C3 C4 C5 C6 -0.6(6)
C4 C5 C6 C1 0.3(5)
C4 C5 C6 C7 179.4(3)
O1 C1 C6 C5 178.6(3)
C2 C1 C6 C5 0.4(5)
O1 C1 C6 C7 -0.5(4)
C2 C1 C6 C7 -178.7(3)
C8 N1 C7 C6 -78.5(4)
C8 N1 C7 P1 155.8(2)
C5 C6 C7 N1 -58.0(4)
C1 C6 C7 N1 121.0(3)
C5 C6 C7 P1 64.4(4)
C1 C6 C7 P1 -116.5(3)
O4 P1 C7 N1 174.96(19)
O3 P1 C7 N1 46.9(2)
O2 P1 C7 N1 -68.6(2)
O4 P1 C7 C6 49.7(2)
O3 P1 C7 C6 -78.4(2)
O2 P1 C7 C6 166.1(2)
C7 N1 C8 N2 -178.6(3)
C7 N1 C8 C9 1.3(5)
C12 N2 C8 N1 177.1(3)
C12 N2 C8 C9 -2.7(5)
N1 C8 C9 C10 -177.7(3)
N2 C8 C9 C10 2.1(5)
C8 C9 C10 C11 -0.4(5)
C9 C10 C11 C12 -0.9(6)
C8 N2 C12 C11 1.5(5)
C10 C11 C12 N2 0.4(6)
P1 O2 C13 C14 -99.2(5)
