#------------------------------------------------------------------------------
#$Date: 2017-10-13 09:09:21 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201973 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/20/95/2209502.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_2209502
loop_
_publ_author_name
'Ullrich, Thomas'
'Pyerin, Michael'
'Mereiter, Kurt'
_publ_section_title
;(3aR,8bR)-(+)-1-Methyl-1,2,3,3a,4,8b-hexahydropyrrolo[2',3':3,4]cyclopenta[1,2-b]pyridine-1,5-diium
 dichloride monohydrate
;
_journal_coeditor_code           GK2008
_journal_issue                   7
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o2958
_journal_page_last               o2960
_journal_paper_doi               10.1107/S1600536806022367
_journal_volume                  62
_journal_year                    2006
_chemical_formula_iupac          'C11 H16 N2 2+ , 2Cl - , H2 O'
_chemical_formula_moiety         'C11 H16 N2 2+ , 2Cl - , H2 O'
_chemical_formula_sum            'C11 H18 Cl2 N2 O'
_chemical_formula_weight         265.17
_chemical_name_systematic
;
(3aR,8bR)-(+)-1-Methyl-1,2,3,3a,4,8b-
hexahydropyrrolo[2',3':3,4]cyclopenta[1,2-b]pyridine-1,5-diium dichloride
monohydrate
;
_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   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL97
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   6.853(3)
_cell_length_b                   8.789(4)
_cell_length_c                   21.537(9)
_cell_measurement_reflns_used    988
_cell_measurement_temperature    295(2)
_cell_measurement_theta_max      27.2
_cell_measurement_theta_min      2.7
_cell_volume                     1297.2(10)
_computing_cell_refinement       'SAINT (Bruker, 2003)'
_computing_data_collection       'SMART (Bruker, 2003)'
_computing_data_reduction        'SAINT, SADABS and XPREP (Bruker, 2003)'
_computing_molecular_graphics    'SHELXTL (Bruker, 2003)'
_computing_publication_material  SHELXTL
_computing_structure_refinement  'SHELXL97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 1997)'
_diffrn_ambient_temperature      295(2)
_diffrn_measured_fraction_theta_full 0.965
_diffrn_measured_fraction_theta_max 0.965
_diffrn_measurement_device_type  'Bruker SMART CCD area-detector'
_diffrn_measurement_method       ω
_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  0.0425
_diffrn_reflns_av_sigmaI/netI    0.0394
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       29
_diffrn_reflns_limit_l_min       -29
_diffrn_reflns_number            17008
_diffrn_reflns_theta_full        29.98
_diffrn_reflns_theta_max         29.98
_diffrn_reflns_theta_min         1.89
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.483
_exptl_absorpt_correction_T_max  0.99
_exptl_absorpt_correction_T_min  0.92
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SADABS; Bruker, 2003)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.358
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             560
_exptl_crystal_size_max          0.55
_exptl_crystal_size_mid          0.07
_exptl_crystal_size_min          0.03
_refine_diff_density_max         0.227
_refine_diff_density_min         -0.201
_refine_ls_abs_structure_details 'Flack (1983), with 1449 Friedel pairs'
_refine_ls_abs_structure_Flack   0.03(7)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.116
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     158
_refine_ls_number_reflns         3554
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.116
_refine_ls_R_factor_all          0.0728
_refine_ls_R_factor_gt           0.0511
_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)+(0.0323P)²+0.2916P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0860
_refine_ls_wR_factor_ref         0.0921
_reflns_number_gt                2829
_reflns_number_total             3554
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            gk2008.cif
_cod_data_source_block           I
_cod_database_code               2209502
_cod_database_fobs_code          2209502
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
Cl Cl1 0.07129(11) 0.92716(8) 0.32361(3) 0.0585(2) Uani d . 1
Cl Cl2 0.87265(8) 0.40559(7) 0.45321(3) 0.04544(15) Uani d . 1
N N1 0.2661(3) 0.6958(2) 0.40512(10) 0.0415(5) Uani d . 1
H H1N 0.213(4) 0.771(3) 0.3811(12) 0.050 Uiso d . 1
N N2 0.5612(3) 0.2368(2) 0.37692(9) 0.0365(4) Uani d . 1
H H2N 0.654(4) 0.284(3) 0.4030(11) 0.044 Uiso d . 1
C C1 0.2824(3) 0.5525(2) 0.38371(11) 0.0356(5) Uani d . 1
C C2 0.3518(3) 0.4403(2) 0.42193(9) 0.0298(4) Uani d . 1
C C3 0.4022(3) 0.4731(3) 0.48276(10) 0.0368(5) Uani d . 1
H H3 0.4491 0.3976 0.5091 0.044 Uiso calc R 1
C C4 0.3808(3) 0.6215(3) 0.50338(11) 0.0434(6) Uani d . 1
H H4 0.4107 0.6466 0.5442 0.052 Uiso calc R 1
C C5 0.3155(3) 0.7306(3) 0.46339(13) 0.0459(6) Uani d . 1
H H5 0.3054 0.8308 0.4769 0.055 Uiso calc R 1
C C6 0.3534(3) 0.2912(2) 0.38838(10) 0.0338(5) Uani d . 1
H H6 0.2763 0.2144 0.4104 0.041 Uiso calc R 1
C C7 0.2667(4) 0.3259(3) 0.32312(12) 0.0417(6) Uani d . 1
H H7 0.1448 0.2695 0.3171 0.050 Uiso calc R 1
C C8 0.4210(4) 0.2709(3) 0.27764(11) 0.0552(7) Uani d . 1
H H8A 0.3998 0.1651 0.2666 0.066 Uiso calc R 1
H H8B 0.4204 0.3319 0.2401 0.066 Uiso calc R 1
C C9 0.6099(4) 0.2901(3) 0.31255(11) 0.0496(6) Uani d . 1
H H9A 0.7125 0.2284 0.2944 0.060 Uiso calc R 1
H H9B 0.6510 0.3957 0.3128 0.060 Uiso calc R 1
C C10 0.5792(4) 0.0686(3) 0.38457(13) 0.0510(6) Uani d . 1
H H10A 0.7071 0.0366 0.3718 0.077 Uiso calc R 1
H H10B 0.4828 0.0187 0.3594 0.077 Uiso calc R 1
H H10C 0.5594 0.0422 0.4274 0.077 Uiso calc R 1
C C11 0.2273(4) 0.4999(3) 0.32114(12) 0.0506(7) Uani d . 1
H H11A 0.3064 0.5488 0.2896 0.061 Uiso calc R 1
H H11B 0.0908 0.5207 0.3128 0.061 Uiso calc R 1
O O1 -0.2776(4) 0.6796(3) 0.36463(12) 0.0777(7) Uani d . 1
H H1OA -0.175(5) 0.742(5) 0.3444(15) 0.093 Uiso d . 1
H H1OB -0.211(6) 0.612(5) 0.3927(17) 0.093 Uiso d . 1
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'
Cl Cl 0.1484 0.1585 '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'
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_publ_flag
C1 C2 C6 110.0(2) y
C3 C2 C6 129.6(2) y
C1 C11 C7 103.8(2) y
C5 N1 C1 121.0(2) ?
C5 N1 H1N 117.8(17) ?
C1 N1 H1N 121.0(17) ?
C10 N2 C9 113.14(18) ?
C10 N2 C6 111.78(18) ?
C9 N2 C6 105.04(18) ?
C10 N2 H2N 108.3(15) ?
C9 N2 H2N 105.1(15) ?
C6 N2 H2N 113.4(15) ?
N1 C1 C2 119.8(2) ?
N1 C1 C11 125.8(2) ?
C2 C1 C11 114.4(2) ?
C1 C2 C3 120.4(2) ?
C4 C3 C2 118.2(2) ?
C4 C3 H3 120.9 ?
C2 C3 H3 120.9 ?
C5 C4 C3 119.6(2) ?
C5 C4 H4 120.2 ?
C3 C4 H4 120.2 ?
N1 C5 C4 121.0(2) ?
N1 C5 H5 119.5 ?
C4 C5 H5 119.5 ?
C2 C6 N2 111.14(17) ?
C2 C6 C7 105.18(17) ?
N2 C6 C7 105.80(18) ?
C2 C6 H6 111.5 ?
N2 C6 H6 111.5 ?
C7 C6 H6 111.5 ?
C8 C7 C11 114.6(2) ?
C8 C7 C6 104.7(2) ?
C11 C7 C6 106.5(2) ?
C8 C7 H7 110.3 ?
C11 C7 H7 110.3 ?
C6 C7 H7 110.3 ?
C9 C8 C7 103.92(19) ?
C9 C8 H8A 111.0 ?
C7 C8 H8A 111.0 ?
C9 C8 H8B 111.0 ?
C7 C8 H8B 111.0 ?
H8A C8 H8B 109.0 ?
N2 C9 C8 103.6(2) ?
N2 C9 H9A 111.0 ?
C8 C9 H9A 111.0 ?
N2 C9 H9B 111.0 ?
C8 C9 H9B 111.0 ?
H9A C9 H9B 109.0 ?
N2 C10 H10A 109.5 ?
N2 C10 H10B 109.5 ?
H10A C10 H10B 109.5 ?
N2 C10 H10C 109.5 ?
H10A C10 H10C 109.5 ?
H10B C10 H10C 109.5 ?
C1 C11 H11A 111.0 ?
C7 C11 H11A 111.0 ?
C1 C11 H11B 111.0 ?
C7 C11 H11B 111.0 ?
H11A C11 H11B 109.0 ?
H1OA O1 H1OB 106(3) ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_publ_flag
N1 C1 1.346(3) y
N1 C5 1.336(3) y
N2 C6 1.523(3) y
N2 C9 1.501(3) y
N2 C10 1.493(3) y
C1 C2 1.370(3) y
C1 C11 1.474(4) y
C2 C3 1.385(3) ?
C2 C6 1.497(3) y
C3 C4 1.385(3) ?
C4 C5 1.364(4) ?
C6 C7 1.556(3) y
C7 C8 1.520(4) y
C8 C9 1.507(4) y
C7 C11 1.553(3) y
N1 H1N 0.91(3) ?
N2 H2N 0.95(3) ?
C3 H3 0.9300 ?
C4 H4 0.9300 ?
C5 H5 0.9300 ?
C6 H6 0.9800 ?
C7 H7 0.9800 ?
C8 H8A 0.9700 ?
C8 H8B 0.9700 ?
C9 H9A 0.9700 ?
C9 H9B 0.9700 ?
C10 H10A 0.9600 ?
C10 H10B 0.9600 ?
C10 H10C 0.9600 ?
C11 H11A 0.9700 ?
C11 H11B 0.9700 ?
O1 H1OA 0.99(4) ?
O1 H1OB 0.96(4) ?
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 H1N Cl1 . 0.91(3) 2.09(3) 3.000(2) 174(2)
N2 H2N Cl2 . 0.95(3) 2.13(3) 3.075(2) 174(2)
O1 H1OA Cl1 . 0.99(4) 2.39(4) 3.351(3) 164(3)
O1 H1OB Cl2 1_455 0.96(4) 2.31(4) 3.240(3) 163(3)
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
C1 C2 C6 C7 -1.9(2) y
C1 C2 C6 N2 112.2(2) y
C2 C6 C7 C8 124.5(2) y
C6 C7 C8 C9 -29.4(3) y
C5 N1 C1 C2 -0.4(3) ?
C5 N1 C1 C11 178.2(2) ?
N1 C1 C2 C3 1.1(3) ?
C11 C1 C2 C3 -177.6(2) ?
N1 C1 C2 C6 179.0(2) ?
C11 C1 C2 C6 0.3(3) ?
C1 C2 C3 C4 -0.2(3) ?
C6 C2 C3 C4 -177.7(2) ?
C2 C3 C4 C5 -1.4(3) ?
C1 N1 C5 C4 -1.2(4) ?
C3 C4 C5 N1 2.1(4) ?
N1 C1 C11 C7 -177.2(2) ?
C2 C1 C11 C7 1.4(3) ?
C1 C11 C7 C8 -117.7(2) ?
C1 C11 C7 C6 -2.5(3) ?
C3 C2 C6 N2 -70.2(3) ?
C3 C2 C6 C7 175.8(2) ?
C10 N2 C6 C2 141.81(19) ?
C9 N2 C6 C2 -95.1(2) ?
C10 N2 C6 C7 -104.5(2) ?
C9 N2 C6 C7 18.5(2) ?
C11 C7 C6 C2 2.7(3) ?
C8 C7 C6 N2 6.7(2) ?
C11 C7 C6 N2 -115.0(2) ?
C11 C7 C8 C9 86.9(3) ?
C10 N2 C9 C8 85.1(3) ?
C6 N2 C9 C8 -37.1(2) ?
C7 C8 C9 N2 41.5(3) ?
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 21179140
