Supplementary Material (ESI) for Organic & Biomolecular Chemistry
  This journal is (c) The Royal Society of Chemistry 2007

data_global

_audit_creation_method           
;
manual editing of the CIF file
created by SHELXTL Ver. 6.14
and processed with modiCIfer-09152005.
;

_journal_coden_Cambridge         177

_publ_contact_author_name        'Patrick Steel'
_publ_contact_author_address     
;
Chemistry Department
Durham University
University Science Laboratories
South Road
Durham
Durham
DH1 3LE
UNITED KINGDOM
;

_publ_contact_author_email       P.G.STEEL@DURHAM.AC.UK

_publ_requested_journal          'Organic & Biomolecular Chemistry'

_publ_section_title              
;
One-pot synthesis of benzothiazolines and
napthathiazolines via cascade ortho-lithiation, cyclisation and
elimination of N-arylsulfonyl lactams
;

_publ_contact_letter             
;
The CIF file contains data for the structure (R,R)-8a from
the paper "One-pot synthesis of benzothiazolines and naphtathiazolines
via cascade ortho-lithiation, cyclisation
and elimination of N-arylsulfonyl lactams"
by J.D.Harling, P.G.Steel, T.M.Woods and D.S.Yufit.
The paper will be submitted to Org.Bioorg.Chem.
;
loop_
_publ_author_name
_publ_author_address
'Harling, John D.'
;
GlaxoSmithKline
Gunnels Wood Road
Stevenage
SG1 2NY
UK
;
'Steel, Patrick G.'
;
Chemistry Department,
University of Durham,
South Rd.,
Durham
DH1 3LE
UK
;
'Woods, Tom M.'
;
Chemistry Department,
University of Durham,
South Rd.,
Durham
DH1 3LE
UK
;
'Yufit, Dmitry S.'
;
Chemistry Department,
University of Durham,
South Rd.,
Durham
DH1 3LE
UK
;

_publ_section_references         
;
Bruker-AXS. (2003). <i>SADABS</i> (Version 2.05), <i>SAINT</i>
(Version 6.22),
<i>SHELXTL</i> (Version 6.10), and <i>SMART</i>
(Version 5.622). Bruker-AXS
Inc., Madison, WI, USA.
;

_publ_section_acknowledgements   
;

The CIF file was prepared with program
<i>modiCIFer</i> to be released by University of Wisconsin-Madison.
;

data_s020
_database_code_depnum_ccdc_archive 'CCDC 650785'
_chemical_name_systematic        
;
3-bromo-4,5,6,7-tetrahydroazepinobenzisothiazole-1,1-dioxide
;
_chemical_name_common            ?
_chemical_melting_point          199-200
_chemical_formula_moiety         'C12 H12 Br N O2 S'
_chemical_formula_sum            'C12 H12 Br N O2 S'
_chemical_formula_weight         314.20

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'

_symmetry_cell_setting           Orthorhombic
_symmetry_space_group_name_H-M   'P b c n '
_symmetry_space_group_name_Hall  '-P 2n 2ab '
_symmetry_int_tables_number      60

loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, -y+1/2, z+1/2'
'-x, y, -z+1/2'
'x+1/2, -y+1/2, -z'
'-x, -y, -z'
'x-1/2, y-1/2, -z-1/2'
'x, -y, z-1/2'
'-x-1/2, y-1/2, z'

_cell_length_a                   16.5525(3)
_cell_length_b                   10.1393(2)
_cell_length_c                   14.0826(3)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_volume                     2363.49(8)
_cell_formula_units_Z            8
_cell_measurement_temperature    120(2)
_cell_measurement_reflns_used    5877
_cell_measurement_theta_min      2.35
_cell_measurement_theta_max      30.37

_exptl_crystal_description       block
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.42
_exptl_crystal_size_mid          0.14
_exptl_crystal_size_min          0.08
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.766
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1264
_exptl_absorpt_coefficient_mu    3.643
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS (Bruker-AXS, 2003)
;
_exptl_absorpt_correction_T_min  0.3099
_exptl_absorpt_correction_T_max  0.7593

_exptl_special_details           
;
?
;

_diffrn_ambient_temperature      120(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           Mo-K\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Bruker SMART CCD 6000'
_diffrn_measurement_method       '0.30\% \w scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         0
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            30330
_diffrn_reflns_av_R_equivalents  0.0259
_diffrn_reflns_av_sigmaI/netI    0.0133
_diffrn_reflns_limit_h_min       -23
_diffrn_reflns_limit_h_max       23
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_theta_min         2.36
_diffrn_reflns_theta_max         30.00
_reflns_number_total             3450
_reflns_number_gt                3023
_reflns_threshold_expression     I>2\s(I)

_computing_data_collection       'SMART Ver. 5.630 (Bruker-AXS, 2003)'
_computing_cell_refinement       'SAINT Ver. 6.45 (Bruker-AXS, 2003)'
_computing_data_reduction        'SAINT Ver. 6.45'
_computing_structure_solution    'SHELXTL Ver. 6.14 (Bruker-AXS, 2003)'
_computing_structure_refinement  'SHELXTL Ver. 6.14'
_computing_molecular_graphics    'SHELXTL Ver. 6.14'
_computing_publication_material  'SHELXTL Ver. 6.14'

_refine_special_details          
;
Refinement of F^2^ against ALL reflections. The weighted R-factor wR and
goodness of fit S are based on F^2^, conventional R-factors R are based
on F, with F set to zero for negative F^2^. The threshold expression of
F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is
not relevant to the choice of reflections for refinement. R-factors based
on F^2^ are statistically about twice as large as those based on F, and R-
factors based on ALL data will be even larger.
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[\s^2^(Fo^2^)+(0.0260P)^2^+2.4000P] where P=(Fo^2^+2Fc^2^)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   difmap
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         3450
_refine_ls_number_parameters     190
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0345
_refine_ls_R_factor_gt           0.0285
_refine_ls_wR_factor_ref         0.0724
_refine_ls_wR_factor_gt          0.0695
_refine_ls_goodness_of_fit_ref   1.145
_refine_ls_restrained_S_all      1.145
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
Br1 Br 0.610748(13) 0.17108(2) 0.185655(17) 0.03361(7) Uani 1 1 d . . .
S1 S 0.58204(3) 0.76966(4) 0.06337(3) 0.02281(10) Uani 1 1 d . A .
O1 O 0.61974(9) 0.86408(15) 0.12537(12) 0.0339(3) Uani 1 1 d . . .
O2 O 0.59623(9) 0.78846(16) -0.03632(11) 0.0317(3) Uani 1 1 d . . .
N1 N 0.48364(9) 0.75992(16) 0.08588(13) 0.0267(3) Uani 1 1 d . . .
C1 C 0.45844(10) 0.63237(17) 0.11453(13) 0.0194(3) Uani 1 1 d . . .
C2 C 0.52927(10) 0.54441(17) 0.11879(12) 0.0187(3) Uani 1 1 d . . .
C3 C 0.60113(10) 0.60744(18) 0.09676(13) 0.0211(3) Uani 1 1 d . A .
C4 C 0.67614(11) 0.5461(2) 0.10080(15) 0.0264(4) Uani 1 1 d . . .
C5 C 0.67898(11) 0.4159(2) 0.12911(14) 0.0266(4) Uani 1 1 d . . .
C6 C 0.60648(11) 0.35043(18) 0.14888(14) 0.0228(3) Uani 1 1 d . . .
C7 C 0.53133(11) 0.41056(18) 0.14283(13) 0.0209(3) Uani 1 1 d . . .
C8 C 0.38333(11) 0.59289(19) 0.13502(14) 0.0243(4) Uani 1 1 d . . .
C9 C 0.30356(12) 0.6630(2) 0.1304(2) 0.0352(5) Uani 1 1 d . A .
C10A C 0.29906(16) 0.8085(3) 0.1505(3) 0.0228(5) Uani 0.70 1 d P A 1
H10A H 0.3150 0.8245 0.2172 0.027 Uiso 0.70 1 calc PR A 1
H10B H 0.2425 0.8383 0.1427 0.027 Uiso 0.70 1 calc PR A 1
C11A C 0.35421(19) 0.8910(3) 0.0843(3) 0.0299(7) Uani 0.70 1 d P A 1
H11A H 0.3364 0.9842 0.0846 0.036 Uiso 0.70 1 calc PR A 1
H11B H 0.3501 0.8574 0.0184 0.036 Uiso 0.70 1 calc PR A 1
C12A C 0.44338(19) 0.8822(3) 0.1185(3) 0.0267(6) Uani 0.70 1 d P A 1
H12A H 0.4736 0.9594 0.0944 0.032 Uiso 0.70 1 calc PR A 1
H12B H 0.4446 0.8853 0.1888 0.032 Uiso 0.70 1 calc PR A 1
C10B C 0.3013(7) 0.8064(11) 0.1133(8) 0.044(3) Uiso 0.30 1 d P A 2
H10C H 0.2798 0.8159 0.0480 0.053 Uiso 0.30 1 calc PR A 2
H10D H 0.2584 0.8399 0.1559 0.053 Uiso 0.30 1 calc PR A 2
C11B C 0.3658(6) 0.9030(11) 0.1199(7) 0.038(3) Uiso 0.30 1 d P A 2
H11C H 0.3448 0.9845 0.0901 0.045 Uiso 0.30 1 calc PR A 2
H11D H 0.3723 0.9227 0.1883 0.045 Uiso 0.30 1 calc PR A 2
C12B C 0.4449(6) 0.8845(10) 0.0833(7) 0.033(2) Uiso 0.30 1 d P A 2
H12C H 0.4437 0.9126 0.0159 0.039 Uiso 0.30 1 calc PR A 2
H12D H 0.4806 0.9473 0.1170 0.039 Uiso 0.30 1 calc PR A 2
H4 H 0.7240(16) 0.592(3) 0.0854(17) 0.035(7) Uiso 1 1 d . . .
H5 H 0.7285(15) 0.376(2) 0.1360(17) 0.029(6) Uiso 1 1 d . . .
H7 H 0.4830(15) 0.366(2) 0.1541(17) 0.024(6) Uiso 1 1 d . . .
H8 H 0.3779(14) 0.505(3) 0.1519(18) 0.030(6) Uiso 1 1 d . . .
H91 H 0.265(2) 0.623(3) 0.168(2) 0.055(9) Uiso 1 1 d . . .
H92 H 0.279(2) 0.643(3) 0.060(2) 0.066(10) Uiso 1 1 d . . .

loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
Br1 0.03036(11) 0.02462(10) 0.04585(13) 0.00735(9) 0.00321(9) 0.00721(7)
S1 0.01659(19) 0.0214(2) 0.0304(2) 0.00220(18) 0.00140(17) -0.00224(15)
O1 0.0290(7) 0.0246(7) 0.0479(10) -0.0050(7) -0.0073(7) -0.0022(6)
O2 0.0266(7) 0.0341(8) 0.0344(8) 0.0092(6) 0.0051(6) -0.0029(6)
N1 0.0181(7) 0.0209(7) 0.0411(9) 0.0054(7) 0.0080(6) 0.0020(6)
C1 0.0178(7) 0.0197(7) 0.0207(8) 0.0011(6) -0.0008(6) 0.0007(6)
C2 0.0149(7) 0.0230(8) 0.0183(7) -0.0013(6) -0.0010(6) 0.0008(6)
C3 0.0176(8) 0.0198(8) 0.0258(8) -0.0007(7) 0.0014(6) -0.0004(6)
C4 0.0164(8) 0.0289(9) 0.0340(10) -0.0009(8) 0.0028(7) -0.0002(7)
C5 0.0189(8) 0.0302(9) 0.0307(10) -0.0023(8) -0.0001(7) 0.0060(7)
C6 0.0239(8) 0.0202(8) 0.0244(8) 0.0005(7) -0.0001(7) 0.0039(7)
C7 0.0189(8) 0.0223(8) 0.0215(8) -0.0011(7) 0.0005(6) -0.0008(6)
C8 0.0177(8) 0.0241(9) 0.0313(10) 0.0022(8) -0.0001(7) 0.0004(7)
C9 0.0171(8) 0.0354(11) 0.0530(14) 0.0028(10) 0.0045(9) 0.0032(8)
C10A 0.0133(11) 0.0301(14) 0.0250(15) -0.0020(12) 0.0045(11) 0.0045(9)
C11A 0.0175(13) 0.0289(15) 0.043(2) 0.0072(15) 0.0033(14) 0.0085(11)
C12A 0.0221(14) 0.0196(13) 0.038(2) 0.0001(14) 0.0089(14) 0.0007(10)

_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_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Br1 C6 1.8921(19) . yes
S1 O2 1.4361(16) . yes
S1 O1 1.4382(16) . yes
S1 N1 1.6623(16) . yes
S1 C3 1.7397(19) . yes
N1 C12B 1.417(11) . yes
N1 C1 1.417(2) . yes
N1 C12A 1.480(3) . yes
C1 C8 1.338(2) . yes
C1 C2 1.474(2) . yes
C2 C3 1.385(2) . yes
C2 C7 1.399(3) . yes
C3 C4 1.390(2) . yes
C4 C5 1.380(3) . yes
C4 H4 0.94(3) . ?
C5 C6 1.399(3) . yes
C5 H5 0.92(2) . ?
C6 C7 1.388(2) . yes
C7 H7 0.94(2) . ?
C8 C9 1.501(3) . yes
C8 H8 0.93(3) . ?
C9 C10B 1.475(11) . yes
C9 C10A 1.504(4) . yes
C9 H91 0.92(3) . ?
C9 H92 1.09(3) . ?
C10A C11A 1.550(5) . yes
C10A H10A 0.9900 . ?
C10A H10B 0.9900 . ?
C11A C12A 1.555(5) . yes
C11A H11A 0.9900 . ?
C11A H11B 0.9900 . ?
C12A H12A 0.9900 . ?
C12A H12B 0.9900 . ?
C10B C11B 1.451(15) . yes
C10B H10C 0.9900 . ?
C10B H10D 0.9900 . ?
C11B C12B 1.421(15) . yes
C11B H11C 0.9900 . ?
C11B H11D 0.9900 . ?
C12B H12C 0.9900 . ?
C12B H12D 0.9900 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
O2 S1 O1 115.73(10) . . yes
O2 S1 N1 110.77(9) . . yes
O1 S1 N1 110.42(9) . . yes
O2 S1 C3 111.10(9) . . yes
O1 S1 C3 112.73(9) . . yes
N1 S1 C3 94.03(8) . . yes
C12B N1 C1 133.4(4) . . yes
C12B N1 C12A 19.6(3) . . yes
C1 N1 C12A 122.89(19) . . yes
C12B N1 S1 112.7(4) . . yes
C1 N1 S1 113.38(12) . . yes
C12A N1 S1 116.78(16) . . yes
C8 C1 N1 127.45(16) . . yes
C8 C1 C2 123.32(16) . . yes
N1 C1 C2 109.23(14) . . yes
C3 C2 C7 118.73(16) . . yes
C3 C2 C1 113.25(15) . . yes
C7 C2 C1 128.02(16) . . yes
C2 C3 C4 123.46(17) . . yes
C2 C3 S1 109.92(13) . . yes
C4 C3 S1 126.62(15) . . yes
C5 C4 C3 118.07(18) . . yes
C5 C4 H4 120.4(16) . . ?
C3 C4 H4 121.5(16) . . ?
C4 C5 C6 118.83(17) . . yes
C4 C5 H5 118.8(15) . . ?
C6 C5 H5 122.3(15) . . ?
C7 C6 C5 123.23(17) . . yes
C7 C6 Br1 118.19(14) . . yes
C5 C6 Br1 118.58(14) . . yes
C6 C7 C2 117.57(16) . . yes
C6 C7 H7 122.8(14) . . ?
C2 C7 H7 119.6(14) . . ?
C1 C8 C9 131.80(19) . . yes
C1 C8 H8 115.6(15) . . ?
C9 C8 H8 112.4(15) . . ?
C10B C9 C8 119.8(5) . . yes
C10B C9 C10A 20.3(4) . . yes
C8 C9 C10A 120.0(2) . . yes
C10B C9 H91 120(2) . . ?
C8 C9 H91 112(2) . . ?
C10A C9 H91 106(2) . . ?
C10B C9 H92 91.4(18) . . ?
C8 C9 H92 106.3(18) . . ?
C10A C9 H92 109.5(18) . . ?
H91 C9 H92 101(3) . . ?
C9 C10A C11A 112.8(3) . . yes
C9 C10A H10A 109.0 . . ?
C11A C10A H10A 109.0 . . ?
C9 C10A H10B 109.0 . . ?
C11A C10A H10B 109.0 . . ?
H10A C10A H10B 107.8 . . ?
C10A C11A C12A 110.0(3) . . yes
C10A C11A H11A 109.7 . . ?
C12A C11A H11A 109.7 . . ?
C10A C11A H11B 109.7 . . ?
C12A C11A H11B 109.7 . . ?
H11A C11A H11B 108.2 . . ?
N1 C12A C11A 112.3(3) . . yes
N1 C12A H12A 109.1 . . ?
C11A C12A H12A 109.1 . . ?
N1 C12A H12B 109.1 . . ?
C11A C12A H12B 109.1 . . ?
H12A C12A H12B 107.9 . . ?
C11B C10B C9 129.5(9) . . yes
C11B C10B H10C 104.9 . . ?
C9 C10B H10C 104.9 . . ?
C11B C10B H10D 104.9 . . ?
C9 C10B H10D 104.9 . . ?
H10C C10B H10D 105.8 . . ?
C12B C11B C10B 124.5(10) . . yes
C12B C11B H11C 106.2 . . ?
C10B C11B H11C 106.2 . . ?
C12B C11B H11D 106.2 . . ?
C10B C11B H11D 106.2 . . ?
H11C C11B H11D 106.4 . . ?
N1 C12B C11B 121.7(8) . . yes
N1 C12B H12C 106.9 . . ?
C11B C12B H12C 106.9 . . ?
N1 C12B H12D 106.9 . . ?
C11B C12B H12D 106.9 . . ?
H12C C12B H12D 106.7 . . ?

_diffrn_measured_fraction_theta_max 0.999
_diffrn_reflns_theta_full        30.00
_diffrn_measured_fraction_theta_full 0.999
_refine_diff_density_max         0.458
_refine_diff_density_min         -0.304
_refine_diff_density_rms         0.070

# File processed with modiCIFer Dec. 16,2005. I.A.Guzei, UW-Madison.