#------------------------------------------------------------------------------
#$Date: 2011-09-10 04:16:28 +0100 (Sat, 10 Sep 2011) $
#$Revision: 25271 $
#$URL: svn://www.crystallography.net/cod/cif/2/2009029.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_2009029
loop_
_publ_author_name
'Farina, A.'
'Meille, S. V.'
'Messina, M. T.'
'Metrangolo, P.'
'Resnati, G.'
_publ_section_title
;
 (--)-Sparteinium bromide
;
_journal_issue                   10
_journal_name_full               'Acta Crystallographica Section C'
_journal_page_first              1710
_journal_page_last               1711
_journal_volume                  55
_journal_year                    1999
_chemical_formula_moiety         'C15 H27 N2 1+, Br 1-'
_chemical_formula_sum            'C15 H27 Br N2'
_chemical_formula_weight         315.30
_chemical_name_systematic
;
(7S)-(7\a,7a\a,14\a,14a\b)-1,3,4,7,7a,8,9,10,11,13,14,14a-Dodecahydro-7,14-
methano-2H,6H-dipyrido[1,2-a:1',2'-e][1,5]diazocin-5-ium bromide
;
_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'
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 101.099(6)
_cell_angle_gamma                90.00
_cell_formula_units_Z            2
_cell_length_a                   8.3779(5)
_cell_length_b                   10.7496(8)
_cell_length_c                   8.3805(5)
_cell_measurement_reflns_used    30
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      16.6
_cell_measurement_theta_min      11.1
_cell_volume                     740.62(8)
_computing_cell_refinement       XSCANS
_computing_data_collection       'XSCANS (Siemens, 1994)'
_computing_data_reduction        XSCANS
_computing_molecular_graphics    'SHELXTL/PC (Sheldrick, 1994)'
_computing_publication_material  SHELXL97
_computing_structure_refinement  'SHELXL97 (Sheldrick, 1997)'
_computing_structure_solution    'SIR97 (Altomare et al., 1994)'
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 0.945
_diffrn_measured_fraction_theta_max 0.945
_diffrn_measurement_device_type  'Siemens P4'
_diffrn_measurement_method       '\q/2\q scan'
_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  0.052
_diffrn_reflns_av_sigmaI/netI    0.052
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_limit_l_min       0
_diffrn_reflns_number            2649
_diffrn_reflns_theta_full        67.99
_diffrn_reflns_theta_max         68
_diffrn_reflns_theta_min         5.38
_diffrn_standards_decay_%        <0.5
_diffrn_standards_interval_count 97
_diffrn_standards_number         3
_exptl_absorpt_coefficient_mu    3.649
_exptl_absorpt_correction_T_max  0.894
_exptl_absorpt_correction_T_min  0.524
_exptl_absorpt_correction_type   integration
_exptl_absorpt_process_details   'XPREP (Siemens, 1997)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.414
_exptl_crystal_density_meas      'not measured'
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             332
_exptl_crystal_size_max          0.25
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.03
_refine_diff_density_max         0.447
_refine_diff_density_min         -0.687
_refine_ls_abs_structure_details 'Flack (1983)'
_refine_ls_abs_structure_Flack   -0.02(6)
_refine_ls_extinction_coef       0.0027(15)
_refine_ls_extinction_method     'SHELXL97 (Sheldrick, 1997)'
_refine_ls_goodness_of_fit_ref   1.099
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     164
_refine_ls_number_reflns         2338
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.098
_refine_ls_R_factor_all          0.091
_refine_ls_R_factor_gt           0.079
_refine_ls_shift/su_max          <0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w = 1/[\s^2^(Fo^2^)+(0.1515P)^2^+0.5774P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_ref         0.228
_reflns_number_gt                1889
_reflns_number_total             2338
_reflns_threshold_expression     I>2\s(I)
_[local]_cod_data_source_file    ka1317.cif
_[local]_cod_data_source_block   mthbr-h1
_[local]_cod_cif_authors_sg_H-M  'P 21'
_cod_original_cell_volume        740.62(7)
_cod_database_code               2009029
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y+1/2, -z'
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
Br1 0.85808(18) 0.74533(13) 1.14789(12) 0.0890(6) Uani d . 1 Br
N16 0.9214(7) 0.7906(6) 0.7302(7) 0.0351(15) Uani d . 1 N
C15 0.7676(9) 0.8636(8) 0.7153(10) 0.0450(19) Uani d . 1 C
H15A 0.7934 0.9517 0.7193 0.054 Uiso calc R 1 H
H15B 0.7168 0.8447 0.8072 0.054 Uiso calc R 1 H
C14 0.6467(12) 0.8358(10) 0.5574(12) 0.056(2) Uani d . 1 C
H14A 0.5457 0.8796 0.5581 0.067 Uiso calc R 1 H
H14B 0.6907 0.8655 0.4655 0.067 Uiso calc R 1 H
C13 0.6131(13) 0.6962(10) 0.5388(13) 0.059(3) Uani d . 1 C
H13A 0.5556 0.6684 0.6222 0.071 Uiso calc R 1 H
H13B 0.5449 0.6798 0.4335 0.071 Uiso calc R 1 H
C12 0.7698(10) 0.6267(8) 0.5534(9) 0.0424(18) Uani d . 1 C
H12A 0.8209 0.6484 0.4626 0.051 Uiso calc R 1 H
H12B 0.7475 0.5381 0.5476 0.051 Uiso calc R 1 H
C11 0.8862(10) 0.6554(8) 0.7113(10) 0.0366(17) Uani d . 1 C
H11 0.8337 0.6296 0.8009 0.044 Uiso calc R 1 H
C17 1.0263(10) 0.8404(9) 0.6217(10) 0.0448(19) Uani d . 1 C
H17A 1.0451 0.9285 0.6419 0.054 Uiso calc R 1 H
H17B 0.9733 0.8297 0.5090 0.054 Uiso calc R 1 H
C7 1.1888(9) 0.7701(8) 0.6546(10) 0.044(2) Uani d . 1 C
H7 1.2562 0.8026 0.5805 0.053 Uiso calc R 1 H
C8 1.1547(11) 0.6337(9) 0.6143(11) 0.0479(19) Uani d . 1 C
H8A 1.2557 0.5872 0.6285 0.057 Uiso calc R 1 H
H8B 1.0983 0.6247 0.5024 0.057 Uiso calc R 1 H
C9 1.0490(10) 0.5858(7) 0.7303(9) 0.0397(17) Uani d . 1 C
H9 1.0257 0.4977 0.7061 0.048 Uiso calc R 1 H
C10 1.1454(11) 0.5955(8) 0.9034(11) 0.0465(19) Uani d . 1 C
H10A 1.0799 0.5642 0.9784 0.056 Uiso calc R 1 H
H10B 1.2422 0.5443 0.9143 0.056 Uiso calc R 1 H
N1 1.1933(7) 0.7257(6) 0.9463(7) 0.0384(14) Uani d . 1 N
H1 1.0999 0.7699 0.9417 0.046 Uiso calc R 1 H
C6 1.2834(9) 0.7840(7) 0.8268(11) 0.047(2) Uani d . 1 C
H6 1.3864 0.7392 0.8340 0.056 Uiso calc R 1 H
C5 1.3242(12) 0.9211(8) 0.8758(13) 0.058(2) Uani d . 1 C
H5A 1.3902 0.9564 0.8040 0.069 Uiso calc R 1 H
H5B 1.2242 0.9687 0.8631 0.069 Uiso calc R 1 H
C4 1.4150(13) 0.9311(10) 1.0504(15) 0.071(3) Uani d . 1 C
H4A 1.5218 0.8937 1.0599 0.085 Uiso calc R 1 H
H4B 1.4295 1.0180 1.0805 0.085 Uiso calc R 1 H
C3 1.3226(14) 0.8661(11) 1.1645(12) 0.067(3) Uani d . 1 C
H3A 1.3866 0.8685 1.2740 0.081 Uiso calc R 1 H
H3B 1.2216 0.9102 1.1648 0.081 Uiso calc R 1 H
C2 1.2856(12) 0.7342(12) 1.1163(10) 0.059(2) Uani d . 1 C
H2A 1.3864 0.6879 1.1260 0.071 Uiso calc R 1 H
H2B 1.2222 0.6969 1.1893 0.071 Uiso calc R 1 H
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
Br1 0.1630(13) 0.0570(7) 0.0593(6) -0.0270(8) 0.0523(6) -0.0099(6)
N16 0.037(3) 0.040(4) 0.029(3) 0.002(3) 0.006(2) -0.002(2)
C15 0.042(4) 0.045(5) 0.045(4) 0.008(4) 0.003(3) -0.005(4)
C14 0.050(5) 0.068(7) 0.044(5) 0.015(5) -0.001(4) -0.003(4)
C13 0.057(5) 0.067(6) 0.046(5) -0.003(4) -0.008(4) -0.005(4)
C12 0.049(4) 0.043(5) 0.034(4) -0.014(4) 0.004(3) -0.005(3)
C11 0.046(4) 0.029(4) 0.034(4) -0.005(3) 0.005(3) 0.002(3)
C17 0.047(4) 0.045(5) 0.042(4) -0.005(4) 0.007(3) 0.005(3)
C7 0.046(4) 0.039(6) 0.052(4) -0.001(4) 0.020(3) -0.004(4)
C8 0.046(4) 0.049(5) 0.051(5) 0.004(4) 0.016(4) -0.012(4)
C9 0.051(4) 0.027(4) 0.040(4) 0.003(3) 0.005(3) -0.008(3)
C10 0.057(5) 0.026(4) 0.052(4) 0.011(4) 0.001(4) 0.007(3)
N1 0.042(3) 0.027(4) 0.042(3) 0.008(3) -0.003(2) -0.003(3)
C6 0.037(4) 0.038(5) 0.065(5) 0.002(3) 0.009(4) -0.009(4)
C5 0.053(5) 0.041(5) 0.077(6) -0.012(4) 0.008(4) -0.005(4)
C4 0.060(6) 0.049(6) 0.098(8) -0.010(5) 0.002(5) -0.029(6)
C3 0.071(6) 0.064(7) 0.056(5) 0.011(5) -0.017(5) -0.018(5)
C2 0.066(5) 0.057(6) 0.046(4) 0.003(6) -0.013(4) -0.002(5)
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'
Br Br -0.6763 1.2805 '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
C17 N16 C11 114.7(7) y
C17 N16 C15 111.3(7) y
C11 N16 C15 110.8(7) y
N16 C15 C14 112.7(7) ?
C13 C14 C15 111.0(8) ?
C12 C13 C14 109.9(9) ?
C13 C12 C11 112.1(7) ?
N16 C11 C12 111.9(7) ?
N16 C11 C9 108.1(6) ?
C12 C11 C9 113.6(7) y
N16 C17 C7 108.8(7) ?
C6 C7 C8 110.4(7) ?
C6 C7 C17 114.0(6) y
C8 C7 C17 108.2(7) ?
C7 C8 C9 107.0(6) y
C10 C9 C8 108.5(7) ?
C10 C9 C11 111.3(7) y
C8 C9 C11 112.5(7) ?
N1 C10 C9 111.4(6) ?
C10 N1 C2 110.9(7) y
C10 N1 C6 112.4(6) y
C2 N1 C6 112.2(6) y
N1 C6 C7 110.9(6) ?
N1 C6 C5 109.5(7) ?
C7 C6 C5 113.2(7) y
C4 C5 C6 111.5(8) ?
C3 C4 C5 110.8(8) ?
C2 C3 C4 111.9(9) ?
N1 C2 C3 111.1(8) ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_publ_flag
N16 C17 1.481(10) y
N16 C11 1.486(11) y
N16 C15 1.494(10) y
C15 C14 1.533(11) ?
C14 C13 1.529(15) ?
C13 C12 1.496(14) ?
C12 C11 1.517(10) ?
C11 C9 1.536(12) ?
C17 C7 1.535(12) ?
C7 C6 1.514(11) ?
C7 C8 1.519(13) ?
C8 C9 1.525(12) ?
C9 C10 1.522(11) ?
C10 N1 1.480(11) y
N1 C2 1.488(9) y
N1 C6 1.502(10) y
C6 C5 1.551(12) ?
C5 C4 1.517(15) ?
C4 C3 1.512(18) ?
C3 C2 1.491(17) ?
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_publ_flag
N1 H1 Br1 2.92 3.552(6) 128 yes
C2 H2B Br1 3.05 3.674(7) 121 yes
C15 H15B Br1 3.06 3.778(7) 132 yes
N1 H1 N16 2.10 2.714(8) 124 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
_geom_torsion_publ_flag
C17 N16 C15 C14 74.6(9) ?
C11 N16 C15 C14 -54.2(10) ?
N16 C15 C14 C13 54.0(12) ?
C15 C14 C13 C12 -53.8(13) ?
C14 C13 C12 C11 55.6(11) ?
C17 N16 C11 C12 -72.0(9) ?
C15 N16 C11 C12 55.0(10) y
C17 N16 C11 C9 53.8(8) ?
C15 N16 C11 C9 -179.2(6) ?
C13 C12 C11 N16 -57.1(10) ?
C13 C12 C11 C9 -179.8(8) ?
C11 N16 C17 C7 -58.8(9) ?
C15 N16 C17 C7 174.5(6) ?
N16 C17 C7 C6 -61.2(9) ?
N16 C17 C7 C8 62.1(8) ?
C6 C7 C8 C9 62.5(8) ?
C17 C7 C8 C9 -62.9(8) ?
C7 C8 C9 C10 -62.9(8) ?
C7 C8 C9 C11 60.7(9) ?
N16 C11 C9 C10 67.4(9) y
C12 C11 C9 C10 -167.7(7) ?
N16 C11 C9 C8 -54.6(9) y
C12 C11 C9 C8 70.3(9) ?
C8 C9 C10 N1 59.8(9) ?
C11 C9 C10 N1 -64.5(9) ?
C9 C10 N1 C2 179.3(7) ?
C9 C10 N1 C6 -54.2(9) ?
C10 N1 C6 C7 52.4(8) ?
C2 N1 C6 C7 178.2(8) ?
C10 N1 C6 C5 178.0(7) ?
C2 N1 C6 C5 -56.2(9) y
C8 C7 C6 N1 -57.1(8) y
C17 C7 C6 N1 65.0(9) y
C8 C7 C6 C5 179.4(7) ?
C17 C7 C6 C5 -58.6(10) ?
N1 C6 C5 C4 54.2(10) ?
C7 C6 C5 C4 178.5(8) ?
C6 C5 C4 C3 -53.7(11) ?
C5 C4 C3 C2 54.8(11) ?
C10 N1 C2 C3 -175.5(8) ?
C6 N1 C2 C3 58.0(10) ?
C4 C3 C2 N1 -56.5(11) ?