##############################################################################
###                                                                        ###
###           Full Paper (Acta Crystallographica Section C)                ###
###                                                                        ###
##############################################################################
#                                                                            #
# This CIF contains the data in a paper accepted for publication in Acta     #
# Crystallographica Section C. It conforms to the editorial and technical    #
# requirements of Notes for Authors for Section C, and has been peer         #
# reviewed under the auspices of the IUCr Commission on Journals.            #
#                                                                            #
# Full details of the Crystallographic Information File format               #
# are given in the paper "The Crystallographic Information File (CIF):       #
# a New Standard Archive File for Crystallography" by S. R. Hall, F. H.      #
# Allen and I. D. Brown [Acta Cryst. (1991), A47, 655-685].                  #
#                                                                            #
# The current version of the core CIF dictionary is obtainable from          #
# ftp://ftp.iucr.org/pub/cif_core.dic. The current version number is 2.1.    #
#                                                                            #
# Software is freely available for graphical display of the structure(s) in  #
# this CIF.  For information consult the CIF home page http://www.iucr.org/  #
# cif/home.html                                                              #
#                                                                            #
#            Copyright International Union of Crystallography                #
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##############################################################################
data_global
_audit_creation_method     'enCIFer editing of SHELXL97 output'
_journal_data_validation_number     ?
_journal_date_recd_electronic     2003-11-25
_journal_date_accepted     2003-11-27
_journal_name_full     'Acta Crystallographica, Section C'
_journal_year     2004
_journal_volume     60
_journal_issue      1
_journal_page_first     o100
_journal_page_last     o102
_journal_paper_category     FO
_publ_contact_author_name     'Dr A.J. Blake'
_publ_contact_author_address
;
  School of Chemistry
  The University of Nottingham
  University Park
  Nottingham  NG7 2RD
  England
;
_publ_contact_author_email     a.j.blake@Nottingham.ac.uk
_publ_contact_author_fax     '0115 951 3563'
_publ_contact_author_phone     '0115 951 3488'
_publ_section_title
;
Intramolecular cyclization of
4,7-bis(2-bromoacetyl)-1-thia-4,7-diazacyclononane
;
loop_
    _publ_author_name
    _publ_author_address
    'Blake, Alexander J.'
; School of Chemistry
  The University of Nottingham
  University Park
  Nottingham  NG7 2RD
  England
;
    'Lippolis, Vito'
; Dipartimento di Chimica
  Inorganica ed Analitica
  Università degli Studi di Cagliari
  Complesso Universitario di Monserrato
  SS 554 bivio per Sestu
  09042 Monserrato (CA)
  Italy
;
    'Schröder, Martin'
; School of Chemistry
  The University of Nottingham
  University Park
  Nottingham  NG7 2RD
  England
;
data_I
_audit_creation_method     SHELXL-97
_chemical_name_systematic     ?
_chemical_name_common     ?
_chemical_formula_moiety     'C10 H16 Br N2 O2 S +, Br -'
_chemical_formula_sum     'C10 H16 Br2 N2 O2 S'
_chemical_formula_iupac     'C10 H16 Br N2 O2 S +, Br -'
_chemical_formula_weight     388.13
_chemical_melting_point     ?
_symmetry_cell_setting     triclinic
_symmetry_space_group_name_H-M     P-1
_symmetry_space_group_name_Hall     '-P 1'
loop_
    _symmetry_equiv_pos_as_xyz
    'x, y, z'
    '-x, -y, -z'
_cell_length_a     7.2655(10)
_cell_length_b     9.5032(13)
_cell_length_c     10.0740(15)
_cell_angle_alpha     86.665(12)
_cell_angle_beta     75.553(13)
_cell_angle_gamma     83.068(10)
_cell_volume     668.36(17)
_cell_formula_units_Z     2
_cell_measurement_reflns_used     56
_cell_measurement_theta_min     12.5
_cell_measurement_theta_max     15
_cell_measurement_temperature     150(2)
_exptl_crystal_description     block
_exptl_crystal_colour     colourless
_exptl_crystal_size_max     0.52
_exptl_crystal_size_mid     0.25
_exptl_crystal_size_min     0.19
_exptl_crystal_density_diffrn     1.929
_exptl_crystal_density_meas     ?
_exptl_crystal_density_method     'not measured'
_exptl_crystal_F_000     384
_exptl_absorpt_coefficient_mu     6.213
_exptl_absorpt_correction_type     psi-scan
_exptl_absorpt_process_details     '(X-RED; Stoe & Cie, 1997)'
_exptl_absorpt_correction_T_min     0.112
_exptl_absorpt_correction_T_max     0.308
_exptl_special_details
;
 ?
;
_diffrn_ambient_temperature     150(2)
_diffrn_radiation_type     MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_monochromator     graphite
_diffrn_measurement_device_type     'Stoe Stadi-4 four-circle'
_diffrn_measurement_method     ω-θ
_diffrn_detector_area_resol_mean     ?
_diffrn_reflns_number     2374
_diffrn_reflns_av_R_equivalents     0.059
_diffrn_reflns_av_sigmaI/netI     0.016
_diffrn_reflns_theta_min     2.09
_diffrn_reflns_theta_max     25.09
_diffrn_reflns_theta_full     25.09
_diffrn_measured_fraction_theta_max     0.993
_diffrn_measured_fraction_theta_full     0.993
_diffrn_reflns_limit_h_min     -8
_diffrn_reflns_limit_h_max     8
_diffrn_reflns_limit_k_min     -11
_diffrn_reflns_limit_k_max     11
_diffrn_reflns_limit_l_min     -2
_diffrn_reflns_limit_l_max     11
_diffrn_standards_number     3
_diffrn_standards_interval_count     ?
_diffrn_standards_interval_time     60
_diffrn_standards_decay_%     0
_refine_special_details
;
  ?
;
_reflns_number_total     2360
_reflns_number_gt     2109
_reflns_threshold_expression     I>2σ(I)
_refine_ls_structure_factor_coef     Fsqd
_refine_ls_matrix_type     full
_refine_ls_R_factor_all     0.0508
_refine_ls_R_factor_gt     0.0460
_refine_ls_wR_factor_gt     0.119
_refine_ls_wR_factor_ref     0.126
_refine_ls_goodness_of_fit_ref     1.05
_refine_ls_restrained_S_all     1.05
_refine_ls_number_reflns     2360
_refine_ls_number_parameters     154
_refine_ls_number_restraints     0
_refine_ls_hydrogen_treatment     constr
_refine_ls_weighting_scheme     calc
_refine_ls_weighting_details
           'calc w=1/[σ²(Fo²)+(0.082P)²+2.906P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_hydrogens     geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary     difmap
_refine_ls_shift/su_max     0.002
_refine_ls_shift/su_mean     0.000
_refine_diff_density_max     1.17
_refine_diff_density_min     -1.48
_refine_ls_extinction_method     none
_refine_ls_extinction_coef     ?
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'
    Br Br -0.2901 2.4595 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
_computing_data_collection     'STADI4 (Stoe & Cie, 1997)'
_computing_cell_refinement     STADI4
_computing_data_reduction     'X-RED (Stoe & Cie, 1997)'
_computing_structure_solution     'SHELXS97 (Sheldrick, 1990)'
_computing_structure_refinement     'SHELXL97 (Sheldrick, 1997)'
_computing_molecular_graphics     'SHELXTL (Bruker, 2001)'
_computing_publication_material
                                  'enCIFer (CCDC, 2003) and PLATON (Spek, 2003)'
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_disorder_assembly
    _atom_site_disorder_group
    _atom_site_type_symbol
    S1 0.04277(17) 0.56457(13) 0.18159(12) 0.0178(3) Uani d . 1 . . S
    C2 0.1873(7) 0.5085(5) 0.3044(5) 0.0210(11) Uani d . 1 . . C
    H2A 0.1004 0.5173 0.3971 0.025 Uiso calc R 1 . . H
    H2B 0.2291 0.4060 0.2914 0.025 Uiso calc R 1 . . H
    C3 0.3633(7) 0.5786(5) 0.3068(5) 0.0207(11) Uani d . 1 . . C
    H3A 0.4518 0.5084 0.3434 0.025 Uiso calc R 1 . . H
    H3B 0.4287 0.6029 0.2111 0.025 Uiso calc R 1 . . H
    N4 0.3297(6) 0.7078(4) 0.3878(4) 0.0159(8) Uani d . 1 . . N
    C5 0.3902(7) 0.8409(5) 0.3181(6) 0.0206(10) Uani d . 1 . . C
    H5A 0.4859 0.8183 0.2311 0.025 Uiso calc R 1 . . H
    H5B 0.4533 0.8890 0.3765 0.025 Uiso calc R 1 . . H
    C6 0.2260(7) 0.9432(5) 0.2867(5) 0.0197(10) Uani d . 1 . . C
    H6A 0.1539 0.9925 0.3710 0.024 Uiso calc R 1 . . H
    H6B 0.2781 1.0156 0.2173 0.024 Uiso calc R 1 . . H
    N7 0.0977(6) 0.8651(4) 0.2351(4) 0.0179(9) Uani d . 1 . . N
    C8 -0.0452(7) 0.8072(5) 0.3281(5) 0.0192(11) Uani d . 1 . . C
    O8 -0.0952(5) 0.8348(4) 0.4496(4) 0.0232(8) Uani d . 1 . . O
    C9 -0.1375(7) 0.6999(5) 0.2703(5) 0.0196(10) Uani d . 1 . . C
    H9A -0.2091 0.7478 0.2057 0.024 Uiso calc R 1 . . H
    H9B -0.2293 0.6549 0.3455 0.024 Uiso calc R 1 . . H
    C10 0.1368(8) 0.8354(6) 0.0883(5) 0.0224(11) Uani d . 1 . . C
    H10A 0.2463 0.8858 0.0380 0.027 Uiso calc R 1 . . H
    H10B 0.0242 0.8743 0.0539 0.027 Uiso calc R 1 . . H
    C11 0.1824(7) 0.6772(5) 0.0554(5) 0.0208(10) Uani d . 1 . . C
    H11A 0.3198 0.6484 0.0491 0.025 Uiso calc R 1 . . H
    H11B 0.1585 0.6631 -0.0352 0.025 Uiso calc R 1 . . H
    C12 0.2591(7) 0.6925(5) 0.5239(6) 0.0208(11) Uani d . 1 . . C
    O12 0.2272(5) 0.5752(4) 0.5793(4) 0.0234(8) Uani d . 1 . . O
    C13 0.2144(7) 0.8203(6) 0.6135(5) 0.0218(11) Uani d . 1 . . C
    H13A 0.0864 0.8190 0.6771 0.026 Uiso calc R 1 . . H
    H13B 0.2143 0.9084 0.5560 0.026 Uiso calc R 1 . . H
    Br 0.41008(8) 0.81431(5) 0.71747(5) 0.0259(2) Uani d . 1 . . Br
    Br1 0.29938(7) 0.26367(6) 0.03575(5) 0.0253(2) Uani d . 1 . . Br
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
    S1 0.0175(6) 0.0153(6) 0.0212(6) 0.0009(5) -0.0069(5) -0.0021(5)
    C2 0.025(3) 0.017(2) 0.024(3) 0.005(2) -0.015(2) -0.001(2)
    C3 0.022(3) 0.016(2) 0.026(3) 0.003(2) -0.011(2) -0.007(2)
    N4 0.016(2) 0.013(2) 0.017(2) 0.0030(16) -0.0039(16) -0.0056(16)
    C5 0.017(2) 0.016(2) 0.029(3) -0.0020(19) -0.005(2) 0.000(2)
    C6 0.022(2) 0.012(2) 0.028(3) -0.0020(19) -0.011(2) 0.001(2)
    N7 0.017(2) 0.016(2) 0.020(2) 0.0009(16) -0.0055(17) 0.0002(16)
    C8 0.015(2) 0.010(2) 0.031(3) 0.0057(18) -0.007(2) 0.002(2)
    O8 0.0257(19) 0.0190(18) 0.0212(19) 0.0033(15) 0.0001(15) -0.0078(14)
    C9 0.014(2) 0.016(2) 0.027(3) 0.0044(19) -0.003(2) -0.005(2)
    C10 0.024(3) 0.022(3) 0.023(3) -0.003(2) -0.008(2) 0.006(2)
    C11 0.021(2) 0.024(3) 0.016(2) 0.003(2) -0.004(2) -0.002(2)
    C12 0.021(2) 0.017(3) 0.030(3) 0.0045(19) -0.016(2) -0.004(2)
    O12 0.031(2) 0.0144(17) 0.0274(19) -0.0011(15) -0.0130(16) 0.0039(15)
    C13 0.024(3) 0.021(3) 0.021(3) 0.005(2) -0.008(2) -0.008(2)
    Br 0.0280(3) 0.0230(3) 0.0301(3) -0.0031(2) -0.0123(2) -0.0044(2)
    Br1 0.0222(3) 0.0301(3) 0.0234(3) 0.0017(2) -0.0073(2) -0.0024(2)
_geom_special_details
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
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
    S1 C2 . 1.831(5) Y
    S1 C9 . 1.819(5) Y
    S1 C11 . 1.803(5) Y
    C2 C3 . 1.518(7) ?
    C3 N4 . 1.476(6) ?
    N4 C12 . 1.345(7) ?
    N4 C5 . 1.471(6) ?
    C5 C6 . 1.530(7) ?
    C6 N7 . 1.464(6) ?
    N7 C8 . 1.361(7) ?
    N7 C10 . 1.472(7) ?
    C10 C11 . 1.537(7) ?
    C8 O8 . 1.221(6) ?
    C8 C9 . 1.502(7) ?
    C12 O12 . 1.238(6) ?
    C12 C13 . 1.511(7) ?
    C13 Br . 1.959(5) ?
    C2 H2A . 0.9900 ?
    C2 H2B . 0.9900 ?
    C3 H3A . 0.9900 ?
    C3 H3B . 0.9900 ?
    C5 H5A . 0.9900 ?
    C5 H5B . 0.9900 ?
    C6 H6A . 0.9900 ?
    C6 H6B . 0.9900 ?
    C9 H9A . 0.9900 ?
    C9 H9B . 0.9900 ?
    C10 H10A . 0.9900 ?
    C10 H10B . 0.9900 ?
    C11 H11A . 0.9900 ?
    C11 H11B . 0.9900 ?
    C13 H13A . 0.9900 ?
    C13 H13B . 0.9900 ?
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 S1 C9 . . 104.1(2) Y
    C2 S1 C11 . . 106.0(2) Y
    C9 S1 C11 . . 98.7(2) Y
    C3 C2 S1 . . 121.9(4) ?
    N4 C3 C2 . . 116.2(4) ?
    C12 N4 C5 . . 124.2(4) ?
    C12 N4 C3 . . 116.9(4) ?
    C5 N4 C3 . . 118.7(4) ?
    N4 C5 C6 . . 113.8(4) ?
    N7 C6 C5 . . 110.0(4) ?
    C8 N7 C6 . . 118.0(4) ?
    C8 N7 C8 . . 120.9(4) ?
    C6 N7 C10 . . 120.7(4) ?
    N7 C10 C11 . . 114.4(4) ?
    C10 C11 S1 . . 113.2(3) ?
    O8 C8 N7 . . 124.6(5) ?
    O8 C8 C9 . . 121.1(5) ?
    N7 C8 C9 . . 114.3(4) ?
    C8 C9 S1 . . 110.4(3) ?
    O12 C12 N4 . . 121.7(5) ?
    O12 C12 C13 . . 118.1(5) ?
    N4 C12 C13 . . 120.1(5) ?
    C12 C13 Br . . 108.4(3) ?
    C3 C2 H2A . . 106.9 ?
    S1 C2 H2A . . 106.9 ?
    C3 C2 H2B . . 106.9 ?
    S1 C2 H2B . . 106.9 ?
    H2A C2 H2B . . 106.7 ?
    N4 C3 H3A . . 108.2 ?
    C2 C3 H3A . . 108.2 ?
    N4 C3 H3B . . 108.2 ?
    C2 C3 H3B . . 108.2 ?
    H3A C3 H3B . . 107.4 ?
    N4 C5 H5A . . 108.8 ?
    C6 C5 H5A . . 108.8 ?
    N4 C5 H5B . . 108.8 ?
    C6 C5 H5B . . 108.8 ?
    H5A C5 H5B . . 107.7 ?
    N7 C6 H6A . . 109.7 ?
    C5 C6 H6A . . 109.7 ?
    N7 C6 H6B . . 109.7 ?
    C5 C6 H6B . . 109.7 ?
    H6A C6 H6B . . 108.2 ?
    C8 C9 H9A . . 109.6 ?
    S1 C9 H9A . . 109.6 ?
    C8 C9 H9B . . 109.6 ?
    S1 C9 H9B . . 109.6 ?
    H9A C9 H9B . . 108.1 ?
    N7 C10 H10A . . 108.7 ?
    C11 C10 H10A . . 108.7 ?
    N7 C10 H10B . . 108.7 ?
    C11 C10 H10B . . 108.7 ?
    H10A C10 H10B . . 107.6 ?
    C10 C11 H11A . . 108.9 ?
    S1 C11 H11A . . 108.9 ?
    C10 C11 H11B . . 108.9 ?
    S1 C11 H11B . . 108.9 ?
    H11A C11 H11B . . 107.7 ?
    C12 C13 H13A . . 110.0 ?
    Br C13 H13A . . 110.0 ?
    C12 C13 H13B . . 110.0 ?
    Br C13 H13B . . 110.0 ?
    H13A C13 H13B . . 108.4 ?
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
    C11 S1 C2 C3 . . . . 12.7(5) ?
    C9 S1 C2 C3 . . . . -90.9(4) ?
    S1 C2 C3 N4 . . . . 85.6(5) ?
    C2 C3 N4 C12 . . . . 64.5(6) ?
    C2 C3 N4 C5 . . . . -120.8(5) ?
    C12 N4 C5 C6 . . . . -83.5(6) ?
    C3 N4 C5 C6 . . . . 102.2(5) ?
    N4 C5 C6 N7 . . . . -42.6(6) ?
    C5 C6 N7 C8 . . . . 86.5(5) ?
    C5 C6 N7 C10 . . . . -86.1(5) ?
    C8 N7 C10 C11 . . . . -57.6(6) ?
    C6 N7 C10 C11 . . . . 114.8(5) ?
    N7 C10 C11 S1 . . . . 37.4(5) ?
    C9 S1 C11 C10 . . . . 14.3(4) ?
    C2 S1 C11 C10 . . . . -93.2(4) ?
    C6 N7 C8 O8 . . . . 13.0(7) ?
    C10 N7 C8 O8 . . . . -174.4(5) ?
    C6 N7 C8 C9 . . . . -165.3(4) ?
    C10 N7 C8 C9 . . . . 7.2(6) ?
    O8 C8 C9 S1 . . . . -125.4(4) ?
    N7 C8 C9 S1 . . . . 53.0(5) ?
    C11 S1 C9 C8 . . . . -59.3(4) ?
    C2 S1 C9 C8 . . . . 49.8(4) ?
    C5 N4 C12 O12 . . . . -173.0(4) ?
    C3 N4 C12 O12 . . . . 1.4(7) ?
    C5 N4 C12 C13 . . . . 7.6(7) ?
    C3 N4 C12 C13 . . . . -178.0(4) ?
    O12 C12 C13 Br . . . . 74.1(5) ?
    N4 C12 C13 Br . . . . -106.5(5) ?
