#------------------------------------------------------------------------------
#$Date: 2017-10-13 10:42:48 +0200 (vie 13 de oct de 2017) $
#$Revision: 201978 $
#$URL: svn://www.crystallography.net/cod/cif/2/22/99/2229955.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_2229955
loop_
_publ_author_name
'Ren, Guo-Bin'
'Qi, Ming-Hui'
'Chen, Jin-Yao'
'Meng, Kun-Yan'
'Zhong, Jia-Liang'
_publ_section_title
;
 1,3-Dihydroxy-2-(hydroxymethyl)propan-2-aminium formate
;
_journal_coeditor_code           CV5073
_journal_issue                   5
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o1264
_journal_paper_doi               10.1107/S1600536811015534
_journal_volume                  67
_journal_year                    2011
_chemical_formula_iupac          'C4 H12 N O3 +, C H O2 -'
_chemical_formula_moiety         'C4 H12 N O3 +, C H O2 -'
_chemical_formula_sum            'C5 H13 N O5'
_chemical_formula_weight         167.16
_chemical_name_systematic
;
1,3-Dihydroxy-2-(hydroxymethyl)propan-2-aminium formate
;
_space_group_IT_number           61
_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_Hall  '-P 2ac 2ab'
_symmetry_space_group_name_H-M   'P b c a'
_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                 90.00
_cell_angle_gamma                90.00
_cell_formula_units_Z            8
_cell_length_a                   6.49800(10)
_cell_length_b                   11.87400(10)
_cell_length_c                   20.5897(2)
_cell_measurement_reflns_used    3109
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      66.80
_cell_measurement_theta_min      7.46
_cell_volume                     1588.64(3)
_computing_cell_refinement       'SAINT (Bruker, 2005)'
_computing_data_collection       'APEX2 (Bruker, 2005)'
_computing_data_reduction        'SAINT (Bruker, 2005)'
_computing_molecular_graphics    'SHELXTL (Sheldrick, 2008)'
_computing_publication_material  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      296(2)
_diffrn_detector_area_resol_mean 0
_diffrn_measured_fraction_theta_full 0.957
_diffrn_measured_fraction_theta_max 0.957
_diffrn_measurement_device_type  'Bruker APEXII'
_diffrn_measurement_method       'φ and ω'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0159
_diffrn_reflns_av_sigmaI/netI    0.0176
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       24
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_number            4402
_diffrn_reflns_theta_full        67.34
_diffrn_reflns_theta_max         67.34
_diffrn_reflns_theta_min         7.46
_diffrn_standards_decay_%        0
_diffrn_standards_interval_count 0
_diffrn_standards_interval_time  0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    1.083
_exptl_absorpt_correction_T_max  0.8994
_exptl_absorpt_correction_T_min  0.7887
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SADABS; Bruker, 2005)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.398
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             720
_exptl_crystal_size_max          0.23
_exptl_crystal_size_mid          0.18
_exptl_crystal_size_min          0.10
_refine_diff_density_max         0.283
_refine_diff_density_min         -0.197
_refine_ls_extinction_coef       0.0049(6)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     'SHELXL97 (Sheldrick, 2008)'
_refine_ls_goodness_of_fit_ref   1.093
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     117
_refine_ls_number_reflns         1368
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.093
_refine_ls_R_factor_all          0.0355
_refine_ls_R_factor_gt           0.0343
_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)+(0.0550P)²+0.4117P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0933
_refine_ls_wR_factor_ref         0.0949
_reflns_number_gt                1304
_reflns_number_total             1368
_reflns_threshold_expression     I>2sigma(I)
_cod_data_source_file            cv5073.cif
_cod_data_source_block           I
_cod_database_code               2229955
_cod_database_fobs_code          2229955
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'-x, y+1/2, -z+1/2'
'x+1/2, -y+1/2, -z'
'-x, -y, -z'
'x-1/2, y, -z-1/2'
'x, -y-1/2, z-1/2'
'-x-1/2, 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
_atom_site_symmetry_multiplicity
_atom_site_disorder_assembly
_atom_site_disorder_group
O O1 0.12876(16) 0.52355(9) 0.22191(4) 0.0392(3) Uani d . 1 1 . .
H H1A 0.1666 0.5765 0.2445 0.059 Uiso calc R 1 1 . .
O O2 0.20496(15) 0.43932(8) 0.02376(4) 0.0340(3) Uani d . 1 1 . .
H H2A 0.2808 0.3926 0.0407 0.051 Uiso calc R 1 1 . .
O O3 0.06605(15) 0.77248(7) 0.07395(5) 0.0349(3) Uani d . 1 1 . .
H H3A -0.0395 0.7945 0.0917 0.052 Uiso calc R 1 1 . .
N N1 -0.06449(16) 0.55746(9) 0.10599(5) 0.0254(3) Uani d . 1 1 . .
C C1 0.16134(18) 0.58258(10) 0.10896(6) 0.0251(3) Uani d . 1 1 . .
C C2 0.2530(2) 0.51726(11) 0.16588(6) 0.0322(3) Uani d . 1 1 . .
H H2B 0.2694 0.4389 0.1535 0.039 Uiso calc R 1 1 . .
H H2C 0.3883 0.5472 0.1758 0.039 Uiso calc R 1 1 . .
C C3 0.2620(2) 0.54863(11) 0.04459(6) 0.0308(3) Uani d . 1 1 . .
H H3B 0.2234 0.6026 0.0114 0.037 Uiso calc R 1 1 . .
H H3C 0.4103 0.5516 0.0495 0.037 Uiso calc R 1 1 . .
C C4 0.1855(2) 0.70956(11) 0.11900(7) 0.0318(3) Uani d . 1 1 . .
H H4A 0.1435 0.7288 0.1628 0.038 Uiso calc R 1 1 . .
H H4B 0.3293 0.7298 0.1142 0.038 Uiso calc R 1 1 . .
O O4 0.23553(18) 0.69672(9) 0.30298(5) 0.0481(3) Uani d . 1 1 . .
O O5 0.22296(18) 0.84393(9) 0.36823(5) 0.0454(3) Uani d . 1 1 . .
C C5 0.1807(2) 0.79327(12) 0.31701(7) 0.0360(4) Uani d . 1 1 . .
H H5A 0.098(3) 0.8304(16) 0.2871(8) 0.051(5) Uiso d . 1 1 . .
H H1B -0.120(3) 0.5727(13) 0.0659(9) 0.040(4) Uiso d . 1 1 . .
H H1C -0.142(2) 0.6018(15) 0.1363(8) 0.041(4) Uiso d . 1 1 . .
H H1D -0.098(3) 0.4814(16) 0.1148(8) 0.044(4) Uiso d . 1 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
O1 0.0514(6) 0.0413(6) 0.0248(5) -0.0045(5) -0.0007(4) -0.0006(4)
O2 0.0468(6) 0.0275(5) 0.0277(5) 0.0099(4) -0.0082(4) -0.0036(3)
O3 0.0403(6) 0.0239(5) 0.0406(6) 0.0002(4) 0.0064(4) 0.0060(4)
N1 0.0302(6) 0.0215(5) 0.0244(6) -0.0025(4) -0.0019(4) 0.0015(4)
C1 0.0274(6) 0.0227(6) 0.0253(6) -0.0020(5) -0.0008(5) -0.0011(5)
C2 0.0378(7) 0.0317(7) 0.0272(7) 0.0042(5) -0.0046(5) -0.0019(5)
C3 0.0352(7) 0.0297(7) 0.0276(7) 0.0003(5) 0.0027(5) -0.0001(5)
C4 0.0354(7) 0.0239(7) 0.0360(7) -0.0044(5) -0.0009(5) -0.0019(5)
O4 0.0633(7) 0.0367(6) 0.0444(6) 0.0148(5) -0.0142(5) -0.0112(4)
O5 0.0551(7) 0.0359(6) 0.0451(6) 0.0153(5) -0.0088(5) -0.0116(4)
C5 0.0388(8) 0.0327(7) 0.0366(8) 0.0069(6) -0.0024(6) -0.0001(6)
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 '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 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 '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_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle
_geom_angle_publ_flag
C2 O1 H1A . . 109.5 ?
C3 O2 H2A . . 109.5 ?
C4 O3 H3A . . 109.5 ?
C1 N1 H1B . . 112.4(11) ?
C1 N1 H1C . . 112.2(10) ?
H1B N1 H1C . . 105.7(14) ?
C1 N1 H1D . . 113.9(10) ?
H1B N1 H1D . . 105.7(14) ?
H1C N1 H1D . . 106.2(14) ?
N1 C1 C2 . . 108.19(10) ?
N1 C1 C4 . . 107.59(10) ?
C2 C1 C4 . . 110.91(10) ?
N1 C1 C3 . . 109.28(10) ?
C2 C1 C3 . . 111.35(10) ?
C4 C1 C3 . . 109.43(10) ?
O1 C2 C1 . . 112.20(10) ?
O1 C2 H2B . . 109.2 ?
C1 C2 H2B . . 109.2 ?
O1 C2 H2C . . 109.2 ?
C1 C2 H2C . . 109.2 ?
H2B C2 H2C . . 107.9 ?
O2 C3 C1 . . 113.05(10) ?
O2 C3 H3B . . 109.0 ?
C1 C3 H3B . . 109.0 ?
O2 C3 H3C . . 109.0 ?
C1 C3 H3C . . 109.0 ?
H3B C3 H3C . . 107.8 ?
O3 C4 C1 . . 111.94(10) ?
O3 C4 H4A . . 109.2 ?
C1 C4 H4A . . 109.2 ?
O3 C4 H4B . . 109.2 ?
C1 C4 H4B . . 109.2 ?
H4A C4 H4B . . 107.9 ?
O4 C5 O5 . . 125.67(14) ?
O4 C5 H5A . . 116.9(12) ?
O5 C5 H5A . . 117.4(11) ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_site_symmetry_2
_geom_bond_distance
_geom_bond_publ_flag
O1 C2 . 1.4100(16) ?
O1 H1A . 0.8200 ?
O2 C3 . 1.4163(16) ?
O2 H2A . 0.8200 ?
O3 C4 . 1.4217(16) ?
O3 H3A . 0.8200 ?
N1 C1 . 1.4987(15) ?
N1 H1B . 0.918(18) ?
N1 H1C . 0.960(18) ?
N1 H1D . 0.946(18) ?
C1 C2 . 1.5265(17) ?
C1 C4 . 1.5299(16) ?
C1 C3 . 1.5317(17) ?
C2 H2B . 0.9700 ?
C2 H2C . 0.9700 ?
C3 H3B . 0.9700 ?
C3 H3C . 0.9700 ?
C4 H4A . 0.9700 ?
C4 H4B . 0.9700 ?
O4 C5 . 1.2348(18) ?
O5 C5 . 1.2449(18) ?
C5 H5A . 0.928(19) ?
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
O1 H1A O4 . 0.82 1.92 2.7378(14) 175
O2 H2A O3 8_655 0.82 1.87 2.6845(12) 173
O3 H3A O5 6_556 0.82 1.85 2.6659(14) 180
N1 H1B O2 5_565 0.918(18) 1.933(19) 2.8233(14) 163.0(15)
N1 H1C O4 6_556 0.960(18) 1.861(18) 2.8171(15) 173.4(15)
N1 H1D O5 3_545 0.946(18) 1.857(19) 2.7876(14) 167.2(15)
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_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion
_geom_torsion_publ_flag
N1 C1 C2 O1 . . . . -43.81(13) ?
C4 C1 C2 O1 . . . . 73.96(13) ?
C3 C1 C2 O1 . . . . -163.92(11) ?
N1 C1 C3 O2 . . . . -48.09(14) ?
C2 C1 C3 O2 . . . . 71.38(14) ?
C4 C1 C3 O2 . . . . -165.66(10) ?
N1 C1 C4 O3 . . . . -49.91(13) ?
C2 C1 C4 O3 . . . . -168.05(10) ?
C3 C1 C4 O3 . . . . 68.72(13) ?
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 30656629
