#------------------------------------------------------------------------------
#$Date: 2011-09-10 06:16:28 +0300 (Sat, 10 Sep 2011) $
#$Revision: 25271 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/2221989.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_2221989
loop_
_publ_author_name
'Yu, Yan-Hong'
'Qian, Kun'
_publ_section_title
;
 1,3-Dihydroxy-2-(hydroxymethyl)propan-2-aminium 2,2-dichloroacetate
;
_journal_coeditor_code           DN2442
_journal_issue                   6
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o1278
_journal_volume                  65
_journal_year                    2009
_chemical_formula_iupac          'C4 H12 N O3 + , C2 H Cl2 O2 -'
_chemical_formula_moiety         'C4 H12 N O3 + , C2 H Cl2 O2 -'
_chemical_formula_sum            'C6 H13 Cl2 N O5'
_chemical_formula_weight         250.07
_chemical_name_systematic
;
1,3-Dihydroxy-2-(hydroxymethyl)propan-2-aminium 2,2-dichloroacetate
;
_space_group_IT_number           4
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  'P 2yb'
_symmetry_space_group_name_H-M   'P 1 21 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                 97.03(3)
_cell_angle_gamma                90.00
_cell_formula_units_Z            2
_cell_length_a                   8.6231(17)
_cell_length_b                   6.1376(12)
_cell_length_c                   9.898(2)
_cell_measurement_reflns_used    735
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      27.4605
_cell_measurement_theta_min      2.7997
_cell_volume                     519.91(18)
_computing_cell_refinement       'CrystalClear (Rigaku, 2005)'
_computing_data_collection       'CrystalClear (Rigaku, 2005)'
_computing_data_reduction        'CrystalClear (Rigaku, 2005)'
_computing_molecular_graphics
;
ORTEPIII (Burnett & Johnson, 1996), ORTEP-3 for Windows (Farrugia,
1997) and
PLATON (Spek, 2009)
;
_computing_publication_material  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      293(2)
_diffrn_detector_area_resol_mean 13.6612
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_device_type  'Rigaku SCXmini'
_diffrn_measurement_method       \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  0.0253
_diffrn_reflns_av_sigmaI/netI    0.0315
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            4914
_diffrn_reflns_theta_full        25.99
_diffrn_reflns_theta_max         25.99
_diffrn_reflns_theta_min         3.34
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.621
_exptl_absorpt_correction_T_max  0.9292
_exptl_absorpt_correction_T_min  0.8754
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(CrystalClear; Rigaku, 2005)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.597
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             260
_exptl_crystal_size_max          0.22
_exptl_crystal_size_mid          0.18
_exptl_crystal_size_min          0.12
_refine_diff_density_max         0.234
_refine_diff_density_min         -0.246
_refine_ls_abs_structure_details 'Flack (1983), 920 Friedel pairs'
_refine_ls_abs_structure_Flack   0.67(6)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.095
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     130
_refine_ls_number_reflns         2044
_refine_ls_number_restraints     3
_refine_ls_restrained_S_all      1.094
_refine_ls_R_factor_all          0.0332
_refine_ls_R_factor_gt           0.0309
_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/[\s^2^(Fo^2^)+(0.0218P)^2^+0.1660P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0682
_refine_ls_wR_factor_ref         0.0693
_reflns_number_gt                1951
_reflns_number_total             2044
_reflns_threshold_expression     I>2\s(I)
_[local]_cod_data_source_file    dn2442.cif
_[local]_cod_data_source_block   I
_[local]_cod_cif_authors_sg_H-M  'P 21'
_cod_original_cell_volume        519.92(18)
_cod_database_code               2221989
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y+1/2, -z'
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
Cl Cl1 0.86491(9) 0.39154(15) 0.00483(7) 0.0630(2) Uani d . 1
Cl Cl2 0.70850(10) 0.03942(11) 0.13016(8) 0.0598(2) Uani d . 1
C C1 0.6938(3) 0.3135(4) 0.0737(2) 0.0342(5) Uani d . 1
H H1 0.6046 0.3263 0.0026 0.041 Uiso calc R 1
C C2 0.6675(2) 0.4656(4) 0.1919(2) 0.0282(5) Uani d . 1
C C3 0.2265(2) 0.2569(3) 0.3756(2) 0.0215(4) Uani d . 1
C C4 0.3748(2) 0.1471(3) 0.3394(2) 0.0248(4) Uani d . 1
H H4A 0.3540 0.0827 0.2496 0.030 Uiso calc R 1
H H4B 0.4558 0.2562 0.3365 0.030 Uiso calc R 1
C C5 0.0883(2) 0.0986(3) 0.3577(2) 0.0249(4) Uani d . 1
H H5A 0.0543 0.0801 0.2613 0.030 Uiso calc R 1
H H5B 0.1226 -0.0423 0.3944 0.030 Uiso calc R 1
C C6 0.1911(2) 0.4607(3) 0.2892(2) 0.0270(4) Uani d . 1
H H6A 0.1841 0.4215 0.1937 0.032 Uiso calc R 1
H H6B 0.0905 0.5188 0.3058 0.032 Uiso calc R 1
N N1 0.25465(19) 0.3243(3) 0.52217(16) 0.0221(3) Uani d . 1
H H1A 0.3470 0.3903 0.5382 0.033 Uiso calc R 1
H H1B 0.2540 0.2070 0.5750 0.033 Uiso calc R 1
H H1C 0.1797 0.4156 0.5403 0.033 Uiso calc R 1
O O1 0.54454(19) 0.5709(3) 0.17435(18) 0.0444(4) Uani d . 1
O O2 0.76863(19) 0.4708(3) 0.29336(16) 0.0403(4) Uani d . 1
O O3 0.42905(16) -0.0160(2) 0.43407(15) 0.0306(4) Uani d D 1
H H3 0.3857 -0.1281 0.4071 0.046 Uiso d RD 1
O O4 0.30642(17) 0.6233(2) 0.31776(17) 0.0336(4) Uani d D 1
H H4 0.3805 0.5959 0.2759 0.050 Uiso d RD 1
O O5 -0.04042(15) 0.1704(3) 0.42311(15) 0.0274(3) Uani d . 1
H H5 -0.0931 0.2564 0.3735 0.041 Uiso calc R 1
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
Cl1 0.0535(4) 0.0984(7) 0.0405(4) -0.0075(4) 0.0196(3) -0.0042(4)
Cl2 0.0872(5) 0.0321(3) 0.0549(4) -0.0001(4) -0.0123(4) -0.0081(3)
C1 0.0339(12) 0.0377(13) 0.0292(11) 0.0008(10) -0.0040(9) -0.0007(10)
C2 0.0274(11) 0.0271(10) 0.0304(11) -0.0002(10) 0.0048(9) 0.0064(9)
C3 0.0185(9) 0.0225(10) 0.0233(10) -0.0014(8) 0.0018(8) 0.0011(8)
C4 0.0213(10) 0.0248(11) 0.0288(11) 0.0005(9) 0.0052(9) 0.0000(9)
C5 0.0191(9) 0.0233(11) 0.0324(11) -0.0007(8) 0.0029(8) -0.0030(9)
C6 0.0247(10) 0.0227(10) 0.0332(11) 0.0007(9) 0.0017(9) 0.0044(9)
N1 0.0180(7) 0.0224(8) 0.0259(9) 0.0000(7) 0.0031(7) -0.0006(7)
O1 0.0347(9) 0.0503(11) 0.0494(10) 0.0142(8) 0.0097(8) 0.0129(9)
O2 0.0424(9) 0.0425(10) 0.0337(9) 0.0120(8) -0.0048(7) -0.0105(7)
O3 0.0238(7) 0.0236(8) 0.0433(9) 0.0036(6) -0.0002(7) 0.0001(7)
O4 0.0293(8) 0.0219(7) 0.0510(10) -0.0038(6) 0.0105(7) 0.0024(7)
O5 0.0179(7) 0.0308(8) 0.0337(8) -0.0002(6) 0.0043(6) 0.0027(6)
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'
Cl Cl 0.1484 0.1585 '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
C2 C1 Cl1 109.75(16)
C2 C1 Cl2 110.36(16)
Cl1 C1 Cl2 110.39(14)
C2 C1 H1 108.8
Cl1 C1 H1 108.8
Cl2 C1 H1 108.8
O1 C2 O2 127.1(2)
O1 C2 C1 114.5(2)
O2 C2 C1 118.38(19)
N1 C3 C6 108.33(17)
N1 C3 C4 107.93(16)
C6 C3 C4 110.28(16)
N1 C3 C5 108.57(16)
C6 C3 C5 110.83(16)
C4 C3 C5 110.81(17)
O3 C4 C3 112.12(16)
O3 C4 H4A 109.2
C3 C4 H4A 109.2
O3 C4 H4B 109.2
C3 C4 H4B 109.2
H4A C4 H4B 107.9
O5 C5 C3 112.99(16)
O5 C5 H5A 109.0
C3 C5 H5A 109.0
O5 C5 H5B 109.0
C3 C5 H5B 109.0
H5A C5 H5B 107.8
O4 C6 C3 112.27(17)
O4 C6 H6A 109.2
C3 C6 H6A 109.2
O4 C6 H6B 109.2
C3 C6 H6B 109.2
H6A C6 H6B 107.9
C3 N1 H1A 109.5
C3 N1 H1B 109.5
H1A N1 H1B 109.5
C3 N1 H1C 109.5
H1A N1 H1C 109.5
H1B N1 H1C 109.5
C4 O3 H3 106.3
C6 O4 H4 109.1
C5 O5 H5 109.5
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
Cl1 C1 1.765(2)
Cl2 C1 1.773(3)
C1 C2 1.536(3)
C1 H1 0.9800
C2 O1 1.236(3)
C2 O2 1.247(3)
C3 N1 1.499(3)
C3 C6 1.525(3)
C3 C4 1.527(3)
C3 C5 1.531(3)
C4 O3 1.411(2)
C4 H4A 0.9700
C4 H4B 0.9700
C5 O5 1.421(2)
C5 H5A 0.9700
C5 H5B 0.9700
C6 O4 1.413(3)
C6 H6A 0.9700
C6 H6B 0.9700
N1 H1A 0.8900
N1 H1B 0.8900
N1 H1C 0.8900
O3 H3 0.8119
O4 H4 0.8205
O5 H5 0.8200
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
N1 H1A O3 2_656 0.89 2.00 2.881(2) 169.2
N1 H1B O2 2_646 0.89 1.97 2.858(2) 171.7
N1 H1C O5 2_556 0.89 2.03 2.909(2) 168.6
O3 H3 O4 1_545 0.81 1.85 2.654(2) 169.3
O4 H4 O1 . 0.82 1.84 2.655(2) 172.6
O5 H5 O2 1_455 0.82 1.88 2.691(2) 167.9