#------------------------------------------------------------------------------
#$Date: 2017-10-13 10:03:29 +0200 (vie 13 de oct de 2017) $
#$Revision: 201974 $
#$URL: svn://www.crystallography.net/cod/cif/2/21/89/2218989.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_2218989
loop_
_publ_author_name
'Fang, Yan-Xiong'
'Huang, Hua-Rong'
'Du, Zhi-Yun'
'Huang, Bao-Hua'
'Zhang, Kun'
_publ_section_title
;
 5-Hydroxy-1-methyl-3,4-dihydro-2H-pyrrolium hydrogensulfate
;
_journal_coeditor_code           FB2100
_journal_issue                   8
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o1622
_journal_paper_doi               10.1107/S1600536808022460
_journal_volume                  64
_journal_year                    2008
_chemical_formula_iupac          'C5 H10 N O +, H S O4 -'
_chemical_formula_moiety         'C5 H10 N O +, H O4 S -'
_chemical_formula_sum            'C5 H11 N O5 S'
_chemical_formula_weight         197.21
_chemical_name_systematic
;
5-Hydroxy-1-methyl-3,4-dihydro-2H-pyrrolium hydrogensulfate
;
_space_group_IT_number           19
_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_Hall  'P 2ac 2ab'
_symmetry_space_group_name_H-M   'P 21 21 21'
_atom_sites_solution_hydrogens   difmap
_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            4
_cell_length_a                   6.5418(14)
_cell_length_b                   10.964(2)
_cell_length_c                   11.614(2)
_cell_measurement_reflns_used    3942
_cell_measurement_temperature    173(2)
_cell_measurement_theta_max      26.99
_cell_measurement_theta_min      2.55
_cell_volume                     833.0(3)
_computing_cell_refinement       'SMART (Bruker, 1999)'
_computing_data_collection       'SMART (Bruker, 1999)'
_computing_data_reduction        'SAINT [or SAINT-Plus?] (Bruker, 1999)'
_computing_molecular_graphics    'SHELXTL (Sheldrick, 2008)'
_computing_publication_material  'SHELXTL (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      173(2)
_diffrn_measured_fraction_theta_full 0.969
_diffrn_measured_fraction_theta_max 0.969
_diffrn_measurement_device_type  'Bruker SMART 1K area-detector'
_diffrn_measurement_method       'φ and ω'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'medium-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0232
_diffrn_reflns_av_sigmaI/netI    0.0258
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_number            4132
_diffrn_reflns_theta_full        25.95
_diffrn_reflns_theta_max         25.95
_diffrn_reflns_theta_min         2.55
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.374
_exptl_absorpt_correction_T_max  0.9223
_exptl_absorpt_correction_T_min  0.8410
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SADABS; Sheldrick, 1996)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.573
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             416
_exptl_crystal_size_max          0.48
_exptl_crystal_size_mid          0.25
_exptl_crystal_size_min          0.22
_refine_diff_density_max         0.279
_refine_diff_density_min         -0.361
_refine_ls_abs_structure_details 'Flack (1983)'
_refine_ls_abs_structure_Flack   0.01(9)
_refine_ls_extinction_coef       0.020(4)
_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   1.195
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_constraints    41
_refine_ls_number_parameters     113
_refine_ls_number_reflns         1578
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.195
_refine_ls_R_factor_all          0.0285
_refine_ls_R_factor_gt           0.0272
_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)+(0.047P)²+0.264P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0883
_refine_ls_wR_factor_ref         0.0892
_reflns_number_gt                1519
_reflns_number_total             1578
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            fb2100.cif
_cod_data_source_block           I
_cod_database_code               2218989
_cod_database_fobs_code          2218989
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'
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
C C1 0.6096(4) 0.42511(19) 0.26605(17) 0.0238(5) Uani d . 1
C C2 0.5508(4) 0.3055(2) 0.31637(19) 0.0275(5) Uani d . 1
H H2A 0.5667 0.2389 0.2596 0.033 Uiso calc R 1
H H2B 0.4078 0.3068 0.3443 0.033 Uiso calc R 1
C C3 0.7017(4) 0.2912(2) 0.4163(2) 0.0346(6) Uani d . 1
H H3A 0.6369 0.3142 0.4902 0.042 Uiso calc R 1
H H3B 0.7507 0.2060 0.4219 0.042 Uiso calc R 1
C C4 0.8773(4) 0.3774(2) 0.38749(19) 0.0296(5) Uani d . 1
H H4A 0.9259 0.4207 0.4571 0.035 Uiso calc R 1
H H4B 0.9932 0.3326 0.3526 0.035 Uiso calc R 1
C C5 0.8878(4) 0.5749(2) 0.2701(2) 0.0309(5) Uani d . 1
H H5A 0.8521 0.5941 0.1902 0.046 Uiso calc R 1
H H5B 1.0361 0.5644 0.2766 0.046 Uiso calc R 1
H H5C 0.8438 0.6418 0.3203 0.046 Uiso calc R 1
N N1 0.7857(3) 0.46269(17) 0.30466(16) 0.0242(4) Uani d . 1
O O1 0.5090(3) 0.48791(14) 0.19136(14) 0.0299(4) Uani d . 1
H H1 0.4010 0.4508 0.1739 0.045 Uiso calc R 1
O O5 0.1546(3) 0.27995(19) -0.05492(17) 0.0434(5) Uani d . 1
O O3 -0.1165(2) 0.40674(14) 0.01936(15) 0.0318(4) Uani d . 1
H H3 -0.1724 0.3407 0.0382 0.048 Uiso calc R 1
O O4 0.1944(3) 0.49886(18) -0.03734(17) 0.0418(5) Uani d . 1
O O2 0.1898(3) 0.37202(16) 0.13185(14) 0.0308(4) Uani d . 1
S S1 0.11940(8) 0.38873(5) 0.01336(4) 0.02365(18) Uani d . 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
C1 0.0289(12) 0.0234(10) 0.0192(9) 0.0026(10) -0.0002(9) -0.0042(7)
C2 0.0325(12) 0.0242(10) 0.0257(10) -0.0049(10) 0.0011(9) -0.0005(9)
C3 0.0380(14) 0.0303(12) 0.0355(13) 0.0013(12) -0.0029(11) 0.0070(10)
C4 0.0296(12) 0.0289(11) 0.0302(10) 0.0052(12) -0.0059(10) 0.0043(9)
C5 0.0342(14) 0.0237(11) 0.0346(11) -0.0064(11) 0.0021(11) -0.0001(8)
N1 0.0266(9) 0.0213(9) 0.0246(9) 0.0022(9) -0.0012(7) -0.0014(7)
O1 0.0322(9) 0.0284(8) 0.0290(8) -0.0007(7) -0.0092(7) 0.0032(6)
O5 0.0456(12) 0.0447(11) 0.0398(9) 0.0131(9) -0.0127(8) -0.0166(8)
O3 0.0246(9) 0.0263(8) 0.0445(9) 0.0001(7) -0.0038(8) 0.0019(7)
O4 0.0416(10) 0.0427(11) 0.0411(11) -0.0084(9) -0.0052(8) 0.0160(8)
O2 0.0332(9) 0.0338(9) 0.0253(8) -0.0011(8) -0.0057(6) 0.0015(7)
S1 0.0244(3) 0.0233(3) 0.0232(3) 0.0004(2) -0.0032(2) 0.00028(19)
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'
S S 0.1246 0.1234 '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
O1 C1 N1 121.0(2)
O1 C1 C2 127.2(2)
N1 C1 C2 111.9(2)
C1 C2 C3 102.82(19)
C1 C2 H2A 111.2
C3 C2 H2A 111.2
C1 C2 H2B 111.2
C3 C2 H2B 111.2
H2A C2 H2B 109.1
C4 C3 C2 104.78(19)
C4 C3 H3A 110.8
C2 C3 H3A 110.8
C4 C3 H3B 110.8
C2 C3 H3B 110.8
H3A C3 H3B 108.9
N1 C4 C3 103.36(19)
N1 C4 H4A 111.1
C3 C4 H4A 111.1
N1 C4 H4B 111.1
C3 C4 H4B 111.1
H4A C4 H4B 109.1
N1 C5 H5A 109.5
N1 C5 H5B 109.5
H5A C5 H5B 109.5
N1 C5 H5C 109.5
H5A C5 H5C 109.5
H5B C5 H5C 109.5
C1 N1 C5 125.3(2)
C1 N1 C4 112.62(19)
C5 N1 C4 122.1(2)
C1 O1 H1 109.5
S1 O3 H3 109.5
O4 S1 O5 114.49(13)
O4 S1 O2 112.65(11)
O5 S1 O2 111.19(11)
O4 S1 O3 104.56(11)
O5 S1 O3 106.63(11)
O2 S1 O3 106.60(10)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
C1 O1 1.288(3)
C1 N1 1.303(3)
C1 C2 1.486(3)
C2 C3 1.532(3)
C2 H2A 0.9900
C2 H2B 0.9900
C3 C4 1.525(4)
C3 H3A 0.9900
C3 H3B 0.9900
C4 N1 1.469(3)
C4 H4A 0.9900
C4 H4B 0.9900
C5 N1 1.457(3)
C5 H5A 0.9800
C5 H5B 0.9800
C5 H5C 0.9800
O1 H1 0.8400
O5 S1 1.4507(19)
O3 S1 1.5576(17)
O3 H3 0.8400
O4 S1 1.4302(19)
O2 S1 1.4626(17)
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
O3 H3 O5 4_455 0.84 1.75 2.569(3) 163.9 yes
O1 H1 O2 . 0.84 1.70 2.540(2) 176.6 yes
C2 H2A O5 4_555 0.99 2.45 3.250(3) 137 yes
C5 H5C O2 3_655 0.98 2.59 3.488(3) 152 yes
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
O1 C1 C2 C3 -168.1(2)
N1 C1 C2 C3 13.3(3)
C1 C2 C3 C4 -20.2(2)
C2 C3 C4 N1 20.1(2)
O1 C1 N1 C5 -0.2(4)
C2 C1 N1 C5 178.53(19)
O1 C1 N1 C4 -179.01(19)
C2 C1 N1 C4 -0.3(3)
C3 C4 N1 C1 -13.0(3)
C3 C4 N1 C5 168.2(2)
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 29737584
