#------------------------------------------------------------------------------
#$Date: 2017-10-13 08:09:21 +0200 (vie 13 de oct de 2017) $
#$Revision: 201973 $
#$URL: svn://www.crystallography.net/cod/cif/2/20/49/2204949.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_2204949
loop_
_publ_author_name
'Shivachev, Boris'
'Petrova, Rosica'
'Kossev, Krassimir'
'Troev, Kolio'
_publ_section_title
;
 [1-(Hydroxyethylammonio)propyl]phosphonate
;
_journal_issue                   1
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o134
_journal_page_last               o136
_journal_paper_doi               10.1107/S1600536804032623
_journal_volume                  61
_journal_year                    2005
_chemical_formula_iupac          'C5 H14 N O4 P'
_chemical_formula_moiety         'C5 H14 N O4 P'
_chemical_formula_sum            'C5 H14 N O4 P'
_chemical_formula_weight         183.14
_chemical_melting_point          378
_chemical_name_common
;
[1-(hydroxyethylamino)propyl]phosphonic acid
;
_chemical_name_systematic
;
[1-(hydroxyethylammonio)propyl]phosphonate
;
_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                 94.77(2)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   9.525(3)
_cell_length_b                   5.992(3)
_cell_length_c                   14.817(2)
_cell_measurement_reflns_used    22
_cell_measurement_temperature    290
_cell_measurement_theta_max      21.10
_cell_measurement_theta_min      19.91
_cell_volume                     842.7(5)
_computing_cell_refinement       'CAD-4 EXPRESS'
_computing_data_collection       'CAD-4 EXPRESS (Enraf-Nonius, 1994)'
_computing_data_reduction        'XCAD4 (Harms & Wocadlo, 1995)'
_computing_molecular_graphics    'ORTEP-3 for Windows (Farrugia, 1997)'
_computing_publication_material  'WinGX (Farrugia, 1999)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 1997)'
_diffrn_ambient_temperature      290
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_device       'κ-geometry diffractometer'
_diffrn_measurement_device_type  'Enraf-Nonius CAD-4'
_diffrn_measurement_method       'non-profiled ω/2θ'
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0211
_diffrn_reflns_av_sigmaI/netI    0.0349
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       0
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_k_min       0
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            1757
_diffrn_reflns_theta_full        25.97
_diffrn_reflns_theta_max         25.97
_diffrn_reflns_theta_min         2.15
_diffrn_standards_decay_%        0
_diffrn_standards_interval_time  120
_diffrn_standards_number         3
_exptl_absorpt_coefficient_mu    0.297
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.444
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    .
_exptl_crystal_description       prism
_exptl_crystal_F_000             392
_exptl_crystal_size_max          0.28
_exptl_crystal_size_mid          0.28
_exptl_crystal_size_min          0.20
_refine_diff_density_max         0.330
_refine_diff_density_min         -0.298
_refine_ls_extinction_coef       0.007(2)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     'SHELXL97 (Sheldrick, 1997)'
_refine_ls_goodness_of_fit_ref   0.877
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     102
_refine_ls_number_reflns         1654
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.877
_refine_ls_R_factor_all          0.0622
_refine_ls_R_factor_gt           0.0421
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w = 1/[σ²(Fo²)+(0.0699P)²+1.1953P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1080
_refine_ls_wR_factor_ref         0.1232
_reflns_number_gt                1305
_reflns_number_total             1654
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            ob6454.cif
_cod_data_source_block           I
_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.

'_geom_torsion_publ_flag' value 'YES' changed to 'yes'
according to '/home/saulius/struct/CIF-dictionaries/cif_core.dic'
dictionary named 'cif_core.dic' version 2.4.1 from 2010-06-29 (2 times).

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.

'_geom_torsion_publ_flag' value 'YES' changed to 'yes'
according to /home/saulius/struct/CIF-dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.1 from 2010-06-29 (2
times).

Automatic conversion script
Id: cif_fix_values 1715 2011-07-08 13:25:40Z adriana 
;
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               2204949
_cod_database_fobs_code          2204949
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_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 0.1577(3) 0.6950(5) 0.33790(18) 0.0314(6) Uani d . 1 C
H1A 0.1595 0.8584 0.3363 0.038 Uiso calc R 1 H
C2 0.2755(3) 0.6217(7) 0.4087(2) 0.0501(9) Uani d . 1 C
H2A 0.3584 0.7109 0.4003 0.060 Uiso calc R 1 H
H2B 0.2462 0.6560 0.4682 0.060 Uiso calc R 1 H
C3 0.3173(4) 0.3778(7) 0.4074(3) 0.0620(11) Uani d . 1 C
H3A 0.2348 0.2864 0.4090 0.093 Uiso calc R 1 H
H3B 0.3814 0.3458 0.4593 0.093 Uiso calc R 1 H
H3C 0.3624 0.3468 0.3532 0.093 Uiso calc R 1 H
C4 0.3184(3) 0.6749(5) 0.2088(2) 0.0378(7) Uani d . 1 C
H4A 0.3932 0.6577 0.2569 0.045 Uiso calc R 1 H
H4B 0.3168 0.8296 0.1895 0.045 Uiso calc R 1 H
C5 0.3469(3) 0.5262(6) 0.1303(2) 0.0448(8) Uani d . 1 C
H5A 0.2639 0.5226 0.0877 0.054 Uiso calc R 1 H
H5B 0.4236 0.5888 0.0994 0.054 Uiso calc R 1 H
O4 0.3820(2) 0.3057(4) 0.15780(18) 0.0550(7) Uani d . 1 O
H4C 0.3167 0.2510 0.1829 0.083 Uiso calc R 1 H
N1 0.1795(2) 0.6157(4) 0.24387(14) 0.0285(5) Uani d . 1 N
H1B 0.1704 0.4662 0.2426 0.034 Uiso calc R 1 H
H1C 0.1102 0.6725 0.2056 0.034 Uiso calc R 1 H
O1 -0.0441(2) 0.7733(3) 0.44645(12) 0.0366(5) Uani d . 1 O
H1D 0.0108 0.7423 0.4902 0.055 Uiso calc R 1 H
O2 -0.11980(19) 0.6732(3) 0.28695(12) 0.0305(5) Uani d . 1 O
O3 -0.02139(19) 0.3719(3) 0.39345(12) 0.0307(5) Uani d . 1 O
P -0.01846(7) 0.61372(11) 0.36636(4) 0.0258(2) Uani d . 1 P
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 0.0359(14) 0.0255(13) 0.0322(14) -0.0025(11) -0.0002(11) -0.0032(11)
C2 0.0387(17) 0.070(2) 0.0403(17) 0.0001(17) -0.0072(13) -0.0063(17)
C3 0.0470(19) 0.083(3) 0.055(2) 0.026(2) -0.0037(16) 0.015(2)
C4 0.0291(14) 0.0350(17) 0.0495(17) -0.0062(12) 0.0050(12) 0.0043(13)
C5 0.0364(16) 0.053(2) 0.0458(18) -0.0055(15) 0.0113(14) 0.0049(15)
O4 0.0390(12) 0.0450(14) 0.0822(18) 0.0081(11) 0.0115(12) -0.0051(13)
N1 0.0268(11) 0.0247(11) 0.0340(12) -0.0008(9) 0.0017(9) 0.0023(10)
O1 0.0559(13) 0.0267(10) 0.0265(10) 0.0091(9) -0.0005(9) -0.0036(8)
O2 0.0346(10) 0.0278(10) 0.0283(10) 0.0020(8) -0.0015(8) 0.0017(8)
O3 0.0426(11) 0.0226(10) 0.0265(9) 0.0016(8) 0.0001(8) 0.0025(8)
P 0.0327(4) 0.0207(4) 0.0237(4) 0.0018(3) 0.0006(2) -0.0003(3)
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_
_diffrn_standard_refln_index_h
_diffrn_standard_refln_index_k
_diffrn_standard_refln_index_l
-1 1 -3
4 -1 -3
0 -1 -5
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
N1 C1 C2 113.2(2)
N1 C1 P 109.23(17)
C2 C1 P 113.5(2)
N1 C1 H1A 106.8
C2 C1 H1A 106.8
P C1 H1A 106.8
C3 C2 C1 116.5(3)
C3 C2 H2A 108.2
C1 C2 H2A 108.2
C3 C2 H2B 108.2
C1 C2 H2B 108.2
H2A C2 H2B 107.3
C2 C3 H3A 109.5
C2 C3 H3B 109.5
H3A C3 H3B 109.5
C2 C3 H3C 109.5
H3A C3 H3C 109.5
H3B C3 H3C 109.5
N1 C4 C5 110.3(2)
N1 C4 H4A 109.6
C5 C4 H4A 109.6
N1 C4 H4B 109.6
C5 C4 H4B 109.6
H4A C4 H4B 108.1
O4 C5 C4 112.5(3)
O4 C5 H5A 109.1
C4 C5 H5A 109.1
O4 C5 H5B 109.1
C4 C5 H5B 109.1
H5A C5 H5B 107.8
C5 O4 H4C 109.5
C4 N1 C1 116.0(2)
C4 N1 H1B 108.3
C1 N1 H1B 108.3
C4 N1 H1C 108.3
C1 N1 H1C 108.3
H1B N1 H1C 107.4
P O1 H1D 109.5
O2 P O3 114.37(11)
O2 P O1 108.66(11)
O3 P O1 112.34(11)
O2 P C1 107.37(12)
O3 P C1 110.82(12)
O1 P C1 102.53(12)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_publ_flag
C1 N1 1.503(3) ?
C1 C2 1.534(4) ?
C1 P 1.830(3) yes
C1 H1A 0.9800 ?
C2 C3 1.515(5) ?
C2 H2A 0.9700 ?
C2 H2B 0.9700 ?
C3 H3A 0.9600 ?
C3 H3B 0.9600 ?
C3 H3C 0.9600 ?
C4 N1 1.503(3) ?
C4 C5 1.508(4) ?
C4 H4A 0.9700 ?
C4 H4B 0.9700 ?
C5 O4 1.415(4) ?
C5 H5A 0.9700 ?
C5 H5B 0.9700 ?
O4 H4C 0.8200 ?
N1 H1B 0.9000 ?
N1 H1C 0.9000 ?
O1 P 1.5590(19) yes
O1 H1D 0.8200 ?
O2 P 1.5013(19) yes
O3 P 1.5046(19) yes
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
O4 H4C O2 2_545 0.82 2.02 2.807(3) 161
N1 H1B O2 2_545 0.90 1.86 2.742(3) 165
N1 H1C O3 2 0.90 2.02 2.873(3) 157
O1 H1D O3 3_566 0.82 1.85 2.555(3) 143
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
_geom_torsion_publ_flag
O1 P C1 N1 -160.84(17) ?
P C1 N1 C4 178.3(2) yes
C1 N1 C4 C5 161.2(2) yes
N1 C4 C5 O4 -72.6(3) ?
O1 P C1 C2 71.8(2) ?
P C1 C2 C3 77.0(3) ?
O2 P C1 N1 -46.5(2) ?
O3 P C1 N1 79.1(2) ?
O2 P C1 C2 -173.8(2) ?
O3 P C1 C2 -48.2(2) ?
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 28577323
