#------------------------------------------------------------------------------
#$Date: 2008-04-03 11:11:48 +0100 (Thu, 03 Apr 2008) $
#$Revision: 326 $
#$URL: svn://www.crystallography.net/cod/cif/2/2206692.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_2206692
loop_
_publ_author_name
'Zhang, Xiang-Dong'
'Yu, Zhan'
'Ma, Yong-Chao'
'Zhao, Zhen'
'Zhu, Miao-Li'
_publ_section_title
;
Ethyl [(2-hydroxyethylammonio)(2-hydroxyphenyl)methyl]phosphonate dihydrate
;
_journal_coeditor_code           HB6242
_journal_issue                   9
_journal_name_full               'Acta Crystallographica, Section E'
_journal_page_first              o2952
_journal_page_last               o2954
_journal_volume                  61
_journal_year                    2005
_chemical_formula_iupac          'C11 H18 N O5 P, 2H2 O'
_chemical_formula_moiety         'C11 H18 N O5 P, 2H2 O'
_chemical_formula_sum            'C11 H22 N O7 P'
_chemical_formula_weight         311.27
_chemical_name_systematic
;
Ethyl
[(2-hydroxyethylammonio)(2-hydroxyphenyl)methyl]phosphonate dihydrate
;
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 21/c'
_atom_sites_solution_hydrogens   'difmap (water O-H) and geom (others)'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 102.80(3)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   7.356(2)
_cell_length_b                   8.707(5)
_cell_length_c                   23.417(8)
_cell_measurement_reflns_used    1375
_cell_measurement_temperature    298(2)
_cell_measurement_theta_max      27.52
_cell_measurement_theta_min      1.78
_cell_volume                     1462.6(11)
_computing_cell_refinement       'SAINT (Bruker, 2000)'
_computing_data_collection       'SMART (Bruker, 2000)'
_computing_data_reduction        SAINT
_computing_molecular_graphics    'SHELXTL/PC (Sheldrick, 1999)'
_computing_publication_material  SHELXTL/PC
_computing_structure_refinement  'SHELXL97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 1997)'
_diffrn_ambient_temperature      298(2)
_diffrn_measured_fraction_theta_full 27.52
_diffrn_measured_fraction_theta_max 0.961
_diffrn_measurement_device_type  'SMART 1K CCD area-detector'
_diffrn_measurement_method       '\f and \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  0.0745
_diffrn_reflns_av_sigmaI/netI    0.0743
_diffrn_reflns_limit_h_max       1
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       26
_diffrn_reflns_limit_l_min       -24
_diffrn_reflns_number            5972
_diffrn_reflns_theta_full        25.03
_diffrn_reflns_theta_max         25.03
_diffrn_reflns_theta_min         1.78
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.218
_exptl_absorpt_correction_T_max  0.968
_exptl_absorpt_correction_T_min  0.958
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SADABS; Sheldrick, 2000)'
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.414
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             664
_exptl_crystal_size_max          0.20
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.15
_refine_diff_density_max         0.250
_refine_diff_density_min         -0.251
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.029
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     184
_refine_ls_number_reflns         2498
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.029
_refine_ls_R_factor_all          0.0832
_refine_ls_R_factor_gt           0.0470
_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^)+(0.0442P)^2^+0.189P] where P = (Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1033
_refine_ls_wR_factor_ref         0.1121
_reflns_number_gt                1718
_reflns_number_total             2498
_reflns_threshold_expression     I>2\s(I)
_[local]_cod_data_source_file    hb6242.cif
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_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_
_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
C1 0.3069(4) 0.0952(3) 0.12570(11) 0.0229(6) Uani d . 1 C
C2 0.3755(4) 0.0109(3) 0.17683(12) 0.0260(7) Uani d . 1 C
O1 0.3413(3) 0.0666(2) 0.22735(8) 0.0376(6) Uani d . 1 O
H1 0.3882 0.0096 0.2545 0.056 Uiso calc R 1 H
C3 0.4750(4) -0.1236(3) 0.17452(14) 0.0324(7) Uani d . 1 C
H3 0.5226 -0.1781 0.2087 0.039 Uiso calc R 1 H
C4 0.5036(4) -0.1770(4) 0.12161(15) 0.0380(8) Uani d . 1 C
H4 0.5676 -0.2685 0.1202 0.046 Uiso calc R 1 H
C5 0.4372(4) -0.0945(4) 0.07081(14) 0.0389(8) Uani d . 1 C
H5 0.4572 -0.1298 0.0352 0.047 Uiso calc R 1 H
C6 0.3402(4) 0.0417(3) 0.07324(13) 0.0330(7) Uani d . 1 C
H6 0.2970 0.0977 0.0391 0.040 Uiso calc R 1 H
C7 0.2019(4) 0.2429(3) 0.13007(11) 0.0228(6) Uani d . 1 C
H7 0.1692 0.2421 0.1684 0.027 Uiso calc R 1 H
N1 0.0221(3) 0.2529(3) 0.08500(9) 0.0251(5) Uani d . 1 N
H1A -0.0283 0.3461 0.0875 0.030 Uiso calc R 1 H
H1B 0.0475 0.2451 0.0492 0.030 Uiso calc R 1 H
C8 -0.1193(4) 0.1330(4) 0.09051(13) 0.0331(7) Uani d . 1 C
H8A -0.0736 0.0325 0.0826 0.040 Uiso calc R 1 H
H8B -0.2343 0.1524 0.0619 0.040 Uiso calc R 1 H
C9 -0.1565(5) 0.1353(4) 0.15099(14) 0.0388(8) Uani d . 1 C
H9A -0.2749 0.0859 0.1506 0.047 Uiso calc R 1 H
H9B -0.0595 0.0788 0.1776 0.047 Uiso calc R 1 H
O2 -0.1608(3) 0.2898(3) 0.17073(11) 0.0439(6) Uani d . 1 O
H2 -0.2692 0.3159 0.1686 0.066 Uiso calc R 1 H
P1 0.34197(10) 0.41641(8) 0.12755(3) 0.0221(2) Uani d . 1 P
O3 0.5035(3) 0.4073(2) 0.17859(8) 0.0310(5) Uani d . 1 O
O4 0.3787(3) 0.4357(2) 0.06832(8) 0.0348(5) Uani d . 1 O
O5 0.1997(3) 0.5486(2) 0.13578(8) 0.0285(5) Uani d . 1 O
C10 0.1590(4) 0.5813(4) 0.19294(12) 0.0333(7) Uani d . 1 C
H10A 0.2669 0.6276 0.2186 0.040 Uiso calc R 1 H
H10B 0.1295 0.4868 0.2109 0.040 Uiso calc R 1 H
C11 -0.0019(6) 0.6882(5) 0.18447(15) 0.0579(11) Uani d . 1 C
H11A 0.0280 0.7810 0.1664 0.087 Uiso calc R 1 H
H11B -0.0290 0.7118 0.2218 0.087 Uiso calc R 1 H
H11C -0.1087 0.6408 0.1597 0.087 Uiso calc R 1 H
O6 0.7417(3) 0.4872(3) 0.04613(9) 0.0496(7) Uani d . 1 O
H61 0.6448 0.4703 0.0572 0.074 Uiso d . 1 H
H62 0.7195 0.4897 0.0104 0.074 Uiso d . 1 H
O7 0.9750(4) 0.7445(3) 0.03541(9) 0.0496(7) Uani d . 1 O
H71 0.8988 0.6831 0.0431 0.074 Uiso d . 1 H
H72 1.0775 0.7290 0.0569 0.074 Uiso d . 1 H
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
C1 0.0170(14) 0.0241(15) 0.0264(15) -0.0007(13) 0.0020(13) 0.0005(12)
C2 0.0216(15) 0.0289(16) 0.0264(16) -0.0036(14) 0.0027(13) 0.0041(12)
O1 0.0446(14) 0.0428(13) 0.0253(11) 0.0114(11) 0.0075(10) 0.0095(9)
C3 0.0257(16) 0.0277(17) 0.0425(19) 0.0009(14) 0.0050(14) 0.0073(13)
C4 0.0254(17) 0.0250(17) 0.061(2) 0.0025(14) 0.0047(17) -0.0044(14)
C5 0.0358(18) 0.0391(19) 0.0416(19) -0.0012(17) 0.0080(16) -0.0134(15)
C6 0.0301(17) 0.0369(18) 0.0305(17) 0.0020(15) 0.0036(14) 0.0006(13)
C7 0.0206(15) 0.0262(15) 0.0206(14) -0.0030(13) 0.0023(12) 0.0007(12)
N1 0.0201(13) 0.0299(13) 0.0240(12) 0.0023(11) 0.0018(10) 0.0004(10)
C8 0.0200(15) 0.0354(17) 0.0417(19) -0.0063(15) 0.0024(14) -0.0046(13)
C9 0.0294(17) 0.0409(19) 0.048(2) -0.0080(16) 0.0128(16) 0.0058(15)
O2 0.0271(12) 0.0506(15) 0.0570(15) 0.0022(11) 0.0161(12) -0.0117(11)
P1 0.0195(4) 0.0250(4) 0.0220(4) -0.0017(3) 0.0051(3) -0.0006(3)
O3 0.0234(11) 0.0372(12) 0.0303(11) -0.0005(10) 0.0015(9) -0.0097(9)
O4 0.0409(13) 0.0399(13) 0.0271(11) -0.0062(11) 0.0149(10) 0.0024(9)
O5 0.0306(12) 0.0267(11) 0.0286(11) 0.0044(9) 0.0072(9) 0.0001(8)
C10 0.0345(18) 0.0369(17) 0.0303(16) 0.0048(15) 0.0110(14) -0.0039(14)
C11 0.054(3) 0.079(3) 0.041(2) 0.033(2) 0.0115(19) -0.0059(18)
O6 0.0370(14) 0.0734(17) 0.0393(14) 0.0078(13) 0.0101(11) 0.0190(12)
O7 0.0531(16) 0.0599(16) 0.0333(12) 0.0032(14) 0.0041(12) 0.0098(11)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_publ_flag
C1 C6 1.385(4) ?
C1 C2 1.400(4) ?
C1 C7 1.515(4) ?
C2 O1 1.353(3) ?
C2 C3 1.388(4) ?
O1 H1 0.8200 ?
C3 C4 1.382(4) ?
C3 H3 0.9300 ?
C4 C5 1.383(4) ?
C4 H4 0.9300 ?
C5 C6 1.391(4) ?
C5 H5 0.9300 ?
C6 H6 0.9300 ?
C7 N1 1.501(4) ?
P1 C7 1.837(3) y
C7 H7 0.9800 ?
N1 C8 1.499(4) ?
N1 H1A 0.9000 ?
N1 H1B 0.9000 ?
C8 C9 1.501(4) ?
C8 H8A 0.9700 ?
C8 H8B 0.9700 ?
C9 O2 1.425(4) ?
C9 H9A 0.9700 ?
C9 H9B 0.9700 ?
O2 H2 0.8200 ?
P1 O4 1.480(2) y
P1 O3 1.489(2) y
P1 O5 1.596(2) y
O5 C10 1.463(3) ?
C10 C11 1.484(4) ?
C10 H10A 0.9700 ?
C10 H10B 0.9700 ?
C11 H11A 0.9600 ?
C11 H11B 0.9600 ?
C11 H11C 0.9600 ?
O6 H61 0.8244 ?
O6 H62 0.8164 ?
O7 H71 0.8230 ?
O7 H72 0.8201 ?
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
C6 C1 C2 118.8(3)
C6 C1 C7 122.6(2)
C2 C1 C7 118.7(2)
O1 C2 C3 122.6(2)
O1 C2 C1 117.3(3)
C3 C2 C1 120.2(3)
C2 O1 H1 109.5
C4 C3 C2 120.3(3)
C4 C3 H3 119.8
C2 C3 H3 119.8
C3 C4 C5 120.1(3)
C3 C4 H4 120.0
C5 C4 H4 120.0
C4 C5 C6 119.6(3)
C4 C5 H5 120.2
C6 C5 H5 120.2
C1 C6 C5 121.0(3)
C1 C6 H6 119.5
C5 C6 H6 119.5
N1 C7 C1 112.6(2)
N1 C7 P1 110.05(18)
C1 C7 P1 113.44(19)
N1 C7 H7 106.8
C1 C7 H7 106.8
P1 C7 H7 106.8
C8 N1 C7 114.8(2)
C8 N1 H1A 108.6
C7 N1 H1A 108.6
C8 N1 H1B 108.6
C7 N1 H1B 108.6
H1A N1 H1B 107.5
N1 C8 C9 110.3(2)
N1 C8 H8A 109.6
C9 C8 H8A 109.6
N1 C8 H8B 109.6
C9 C8 H8B 109.6
H8A C8 H8B 108.1
O2 C9 C8 109.9(3)
O2 C9 H9A 109.7
C8 C9 H9A 109.7
O2 C9 H9B 109.7
C8 C9 H9B 109.7
H9A C9 H9B 108.2
C9 O2 H2 109.5
O4 P1 O3 118.65(13)
O4 P1 O5 106.98(12)
O3 P1 O5 111.70(11)
O4 P1 C7 110.08(12)
O3 P1 C7 106.48(12)
O5 P1 C7 101.64(12)
C10 O5 P1 121.56(17)
O5 C10 C11 108.6(2)
O5 C10 H10A 110.0
C11 C10 H10A 110.0
O5 C10 H10B 110.0
C11 C10 H10B 110.0
H10A C10 H10B 108.4
C10 C11 H11A 109.5
C10 C11 H11B 109.5
H11A C11 H11B 109.5
C10 C11 H11C 109.5
H11A C11 H11C 109.5
H11B C11 H11C 109.5
H61 O6 H62 109.8
H71 O7 H72 109.7
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
C6 C1 C2 O1 179.7(3)
C7 C1 C2 O1 0.8(4)
C6 C1 C2 C3 0.0(4)
C7 C1 C2 C3 -179.0(3)
O1 C2 C3 C4 178.9(3)
C1 C2 C3 C4 -1.4(4)
C2 C3 C4 C5 1.6(5)
C3 C4 C5 C6 -0.6(5)
C2 C1 C6 C5 1.1(4)
C7 C1 C6 C5 180.0(3)
C4 C5 C6 C1 -0.8(5)
C6 C1 C7 N1 49.0(4)
C2 C1 C7 N1 -132.0(3)
C6 C1 C7 P1 -76.8(3)
C2 C1 C7 P1 102.1(3)
C1 C7 N1 C8 63.6(3)
P1 C7 N1 C8 -168.72(18)
C7 N1 C8 C9 54.7(3)
N1 C8 C9 O2 39.4(3)
N1 C7 P1 O4 -58.0(2)
C1 C7 P1 O4 69.2(2)
N1 C7 P1 O3 172.22(17)
C1 C7 P1 O3 -60.6(2)
N1 C7 P1 O5 55.2(2)
C1 C7 P1 O5 -177.62(18)
O4 P1 O5 C10 -168.8(2)
O3 P1 O5 C10 -37.4(2)
C7 P1 O5 C10 75.8(2)
P1 O5 C10 C11 -169.6(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
N1 H1A O5 . 0.90 2.52 3.010(3) 115 Y
N1 H1A O6 1_455 0.90 2.14 2.901(3) 142 Y
N1 H1B O7 3_665 0.90 1.95 2.825(3) 162 Y
O1 H1 O3 2_645 0.82 1.82 2.639(3) 172 Y
O2 H2 O3 1_455 0.82 1.91 2.716(3) 167 Y
O6 H61 O4 . 0.82 2.05 2.866(3) 169 Y
O6 H62 O4 3_665 0.82 1.94 2.714(3) 159 Y
O7 H72 O5 1_655 0.82 2.44 3.073(3) 135 Y
O7 H71 O6 . 0.82 2.07 2.867(4) 163 Y