##############################################################################
###                                                                        ###
###        Electronic paper (Acta Crystallographica Section E)             ###
###                                                                        ###
##############################################################################
#                                                                            #
# This CIF contains the data in a paper accepted for publication in Acta     #
# Crystallographica Section E. It conforms to the requirements of Notes      #
# for Authors for Section E, 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                #
#                                                                            #
##############################################################################
                                             
data_I
_audit_creation_method     SHELXL-97
_chemical_name_systematic
;
[3aS-(3aα,6α,7β)]-7-bromo-4,5,6,7-tetrahydro-8,8-dimethyl-
3H-3a,6-methano-2,1-benzisothiazole-2,2-dioxide
;
_chemical_name_common
;
7-β-bromo-(-)-camphorsulfonimide
;
_chemical_formula_moiety     'C10 H14 Br N O2 S'
_chemical_formula_sum     'C10 H14 Br N O2 S'
_chemical_formula_iupac     'C10 H14 Br N O2 S'
_chemical_formula_weight     292.19
_chemical_melting_point     ?
_symmetry_cell_setting     orthorhombic
_symmetry_space_group_name_H-M     'P 21 21 21'
_symmetry_space_group_name_Hall     ' P 2ac 2ab'
loop_
    _symmetry_equiv_pos_as_xyz
    'x, y, z'
    '-x+1/2, -y, z+1/2'
    'x+1/2, -y+1/2, -z'
    '-x, y+1/2, -z+1/2'
_cell_length_a     7.2643(4)
_cell_length_b     10.6393(6)
_cell_length_c     15.6331(13)
_cell_angle_alpha     90
_cell_angle_beta     90
_cell_angle_gamma     90
_cell_volume     1208.24(14)
_cell_formula_units_Z     4
_cell_measurement_reflns_used     25
_cell_measurement_theta_min     11.3
_cell_measurement_theta_max     34.0
_cell_measurement_temperature     296
_exptl_crystal_description     fragment
_exptl_crystal_colour     'colorless'
_exptl_crystal_size_max      .23
_exptl_crystal_size_mid      .22
_exptl_crystal_size_min      .15
_exptl_crystal_density_diffrn     1.606
_exptl_crystal_density_meas     ?
_exptl_crystal_density_method     'not measured'
_exptl_crystal_F_000     592
_exptl_absorpt_coefficient_mu     6.11
_exptl_absorpt_correction_type     '\y scan'
_exptl_absorpt_process_details     '(North et al., 1968)'
_exptl_absorpt_correction_T_min      .267
_exptl_absorpt_correction_T_max      .399
_exptl_special_details
;
 ?
;
_diffrn_ambient_temperature     296
_diffrn_radiation_type     CuK\a
_diffrn_radiation_wavelength     1.54180
_diffrn_radiation_source     'fine-focus sealed tube'
_diffrn_radiation_monochromator     graphite
_diffrn_measurement_device     'Enraf-Nonius CAD-4'
_diffrn_measurement_method     θ/2θ
_diffrn_detector_area_resol_mean     ?
_diffrn_reflns_number     5380
_diffrn_reflns_av_R_equivalents      .057
_diffrn_reflns_av_sigmaI/netI      .0093
_diffrn_reflns_theta_min     5.0
_diffrn_reflns_theta_max     74.9
_diffrn_reflns_theta_full     74.9
_diffrn_measured_fraction_theta_max     1.000
_diffrn_measured_fraction_theta_full     1.000
_diffrn_reflns_limit_h_min     0
_diffrn_reflns_limit_h_max     9
_diffrn_reflns_limit_k_min     -13
_diffrn_reflns_limit_k_max     13
_diffrn_reflns_limit_l_min     -19
_diffrn_reflns_limit_l_max     19
_diffrn_standards_number     3
_diffrn_standards_interval_count     ?
_diffrn_standards_interval_time     120
_diffrn_standards_decay_%     9.0
_refine_special_details
;
 Refinement of F² against ALL reflections.  The weighted R-factor wR and
 goodness of fit S are based on F², conventional R-factors R are based
 on F, with F set to zero for negative F². The threshold expression of
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is
 not relevant to the choice of reflections for refinement.  R-factors based
 on F² are statistically about twice as large as those based on F, and R-
 factors based on ALL data will be even larger.
;
_reflns_number_total     2484
_reflns_number_gt     2348
_reflns_threshold_expression     I>2σ(I)
_refine_ls_structure_factor_coef     Fsqd
_refine_ls_matrix_type     full
_refine_ls_R_factor_all      .061
_refine_ls_R_factor_gt      .057
_refine_ls_wR_factor_ref      .162
_refine_ls_goodness_of_fit_ref     1.152
_refine_ls_restrained_S_all     1.152
_refine_ls_number_reflns     2484
_refine_ls_number_parameters     138
_refine_ls_number_restraints     0
_refine_ls_hydrogen_treatment     constr
_refine_ls_weighting_scheme     calc
_refine_ls_weighting_details
     'calc w = 1/[σ²(Fo²)+(0.0977P)²+0.6776P] where P = (Fo²+2Fc²)/3'
_refine_ls_shift/su_max     <0.001
_refine_ls_shift/su_mean      .000
_refine_diff_density_max      .89
_refine_diff_density_min      -.81
_refine_ls_extinction_method     none
_refine_ls_extinction_coef     ?
_refine_ls_abs_structure_details     'Flack (1983), 1033 Friedel pairs'
_refine_ls_abs_structure_Flack      .02(4)
loop_
    _atom_type_symbol
    _atom_type_description
    _atom_type_scat_dispersion_real
    _atom_type_scat_dispersion_imag
    _atom_type_scat_source
    'C' 'C'  .0181  .0091
                         'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
    'H' 'H'  .0000  .0000
                         'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
    'O' 'O'  .0492  .0322
                         'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
    'Br' 'Br'  -.6763 1.2805
                         'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
    'N' 'N'  .0311  .0180
                         'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
    'S' 'S'  .3331  .5567
                         'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
_computing_data_collection     'CAD-4 EXPRESS (Enraf-Nonius, 1994)'
_computing_cell_refinement     'CAD-4 EXPRESS'
_computing_data_reduction     'maXus (Mackay et al., 1999)'
_computing_structure_solution     'SIR97 (Altomare et al., 1999)'
_computing_structure_refinement     'SHELXL97 (Sheldrick, 1997)'
_computing_molecular_graphics     'ORTEP-3 for Windows (Farrugia, 1997)'
_computing_publication_material     'SHELXL97'
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
    Br  .59132(12)  .63333(8)  .01579(5)  .1019(3) Uani d . 1 . . Br
    S  .53225(19)  .45051(10)  .30589(7)  .0622(3) Uani d . 1 . . S
    O1  .6825(7)  .3659(4)  .2999(3)  .0865(12) Uani d . 1 . . O
    O2  .5099(10)  .5173(5)  .3830(3)  .1043(17) Uani d . 1 . . O
    N  .5533(5)  .5566(3)  .2262(2)  .0523(8) Uani d . 1 . . N
    C1  .3829(7)  .5989(4)  .0899(3)  .0557(10) Uani d . 1 . . C
    H1  .3270  .6792  .1064  .067 Uiso calc R 1 . . H
    C2  .4345(5)  .5295(3)  .1694(2)  .0462(8) Uani d . 1 . . C
    C3  .3080(6)  .4175(4)  .1775(3)  .0559(10) Uani d . 1 . . C
    C4  .3776(9)  .3256(4)  .1077(4)  .0745(15) Uani d . 1 . . C
    H4A  .5101  .3151  .1108  .089 Uiso calc R 1 . . H
    H4B  .3193  .2439  .1131  .089 Uiso calc R 1 . . H
    C5  .3207(12)  .3906(5)  .0238(4)  .0860(18) Uani d . 1 . . C
    H5A  .4272  .4062  -.0121  .103 Uiso calc R 1 . . H
    H5B  .2332  .3397  -.0077  .103 Uiso calc R 1 . . H
    C6  .2327(8)  .5144(4)  .0527(3)  .0667(13) Uani d . 1 . . C
    H6  .1540  .5548  .0098  .080 Uiso calc R 1 . . H
    C7  .3199(8)  .3770(5)  .2696(4)  .0685(12) Uani d . 1 . . C
    H7A  .3266  .2862  .2744  .082 Uiso calc R 1 . . H
    H7B  .2150  .4071  .3021  .082 Uiso calc R 1 . . H
    C8  .1301(6)  .4733(4)  .1372(4)  .0654(12) Uani d . 1 . . C
    C9  .0480(7)  .5805(5)  .1894(5)  .0823(17) Uani d . 1 . . C
    H9A  -.0494  .6195  .1575  .123 Uiso calc R 1 . . H
    H9B  .1419  .6415  .2015  .123 Uiso calc R 1 . . H
    H9C  -.0001  .5480  .2422  .123 Uiso calc R 1 . . H
    C10  -.0240(10)  .3749(6)  .1239(6)  .105(3) Uani d . 1 . . C
    H10A  .0293  .2969  .1056  .157 Uiso calc R 1 . . H
    H10B  -.1084  .4045  .0812  .157 Uiso calc R 1 . . H
    H10C  -.0886  .3623  .1768  .157 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
    Br  .1102(6)  .1140(6)  .0815(5)  .0030(4)  .0237(4)  .0414(4)
    S  .0850(7)  .0506(5)  .0511(5)  -.0087(5)  -.0022(5)  .0113(4)
    O1  .086(2)  .072(2)  .101(3)  .006(2)  -.017(2)  .030(2)
    O2  .169(5)  .092(3)  .0521(19)  -.031(3)  .011(3)  -.0027(19)
    N  .0623(19)  .0404(14)  .0540(18)  -.0051(15)  .0009(15)  .0081(13)
    C1  .066(2)  .0450(18)  .057(2)  .0077(17)  -.0018(19)  .0058(17)
    C2  .0517(18)  .0362(14)  .0507(19)  .0042(15)  .0037(16)  .0020(14)
    C3  .060(2)  .0390(18)  .069(3)  -.0045(17)  -.001(2)  -.0031(17)
    C4  .088(3)  .043(2)  .093(4)  .014(2)  -.006(3)  -.015(2)
    C5  .126(5)  .055(3)  .077(3)  .014(3)  -.009(3)  -.027(3)
    C6  .085(3)  .050(2)  .065(3)  .015(2)  -.022(2)  -.014(2)
    C7  .078(3)  .049(2)  .078(3)  -.011(2)  .012(3)  .014(2)
    C8  .055(2)  .0415(18)  .100(4)  -.0058(17)  -.009(2)  -.014(2)
    C9  .055(2)  .063(3)  .129(5)  .006(2)  .004(3)  -.024(3)
    C10  .076(3)  .079(4)  .159(7)  -.020(3)  -.029(4)  -.022(4)
_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
    Br C1 . 1.941(5) yes
    S O2 . 1.408(5) yes
    S O1 . 1.418(5) yes
    S N . 1.687(3) yes
    S C7 . 1.820(6) yes
    N C2 . 1.271(6) yes
    C1 C2 . 1.494(6) ?
    C1 C6 . 1.529(7) ?
    C1 H1 .  .9800 ?
    C2 C3 . 1.510(5) ?
    C3 C7 . 1.505(7) ?
    C3 C4 . 1.550(7) ?
    C3 C8 . 1.556(7) ?
    C4 C5 . 1.539(9) ?
    C4 H4A .  .9700 ?
    C4 H4B .  .9700 ?
    C5 C6 . 1.532(7) ?
    C5 H5A .  .9700 ?
    C5 H5B .  .9700 ?
    C6 C8 . 1.578(9) ?
    C6 H6 .  .9800 ?
    C7 H7A .  .9700 ?
    C7 H7B .  .9700 ?
    C8 C9 . 1.524(7) ?
    C8 C10 . 1.547(7) ?
    C9 H9A .  .9600 ?
    C9 H9B .  .9600 ?
    C9 H9C .  .9600 ?
    C10 H10A .  .9600 ?
    C10 H10B .  .9600 ?
    C10 H10C .  .9600 ?
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
    O2 S O1 . . 117.7(4) yes
    O2 S N . . 107.7(2) yes
    O1 S N . . 107.8(2) yes
    O2 S C7 . . 112.7(4) yes
    O1 S C7 . . 111.1(2) yes
    N S C7 . . 97.7(2) yes
    C2 N S . . 107.6(3) yes
    C2 C1 C6 . . 101.8(4) ?
    C2 C1 Br . . 113.2(3) ?
    C6 C1 Br . . 116.1(3) ?
    C2 C1 H1 . . 108.4 ?
    C6 C1 H1 . . 108.4 ?
    Br C1 H1 . . 108.4 ?
    N C2 C1 . . 129.7(4) ?
    N C2 C3 . . 122.2(4) ?
    C1 C2 C3 . . 107.9(4) ?
    C7 C3 C2 . . 105.7(4) ?
    C7 C3 C4 . . 118.4(4) ?
    C2 C3 C4 . . 103.9(4) ?
    C7 C3 C8 . . 123.0(5) ?
    C2 C3 C8 . . 99.8(3) ?
    C4 C3 C8 . . 103.1(4) ?
    C5 C4 C3 . . 103.2(4) ?
    C5 C4 H4A . . 111.1 ?
    C3 C4 H4A . . 111.1 ?
    C5 C4 H4B . . 111.1 ?
    C3 C4 H4B . . 111.1 ?
    H4A C4 H4B . . 109.1 ?
    C6 C5 C4 . . 104.4(4) ?
    C6 C5 H5A . . 110.9 ?
    C4 C5 H5A . . 110.9 ?
    C6 C5 H5B . . 110.9 ?
    C4 C5 H5B . . 110.9 ?
    H5A C5 H5B . . 108.9 ?
    C1 C6 C5 . . 108.6(5) ?
    C1 C6 C8 . . 100.5(4) ?
    C5 C6 C8 . . 101.8(4) ?
    C1 C6 H6 . . 114.8 ?
    C5 C6 H6 . . 114.8 ?
    C8 C6 H6 . . 114.8 ?
    C3 C7 S . . 102.9(3) ?
    C3 C7 H7A . . 111.2 ?
    S C7 H7A . . 111.2 ?
    C3 C7 H7B . . 111.2 ?
    S C7 H7B . . 111.2 ?
    H7A C7 H7B . . 109.1 ?
    C9 C8 C10 . . 107.2(5) ?
    C9 C8 C3 . . 113.2(5) ?
    C10 C8 C3 . . 113.4(4) ?
    C9 C8 C6 . . 115.2(4) ?
    C10 C8 C6 . . 114.7(6) ?
    C3 C8 C6 . . 93.0(4) yes
    C8 C9 H9A . . 109.5 ?
    C8 C9 H9B . . 109.5 ?
    H9A C9 H9B . . 109.5 ?
    C8 C9 H9C . . 109.5 ?
    H9A C9 H9C . . 109.5 ?
    H9B C9 H9C . . 109.5 ?
    C8 C10 H10A . . 109.5 ?
    C8 C10 H10B . . 109.5 ?
    H10A C10 H10B . . 109.5 ?
    C8 C10 H10C . . 109.5 ?
    H10A C10 H10C . . 109.5 ?
    H10B C10 H10C . . 109.5 ?
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
    O2 S N C2 . . . . -126.6(4) ?
    O1 S N C2 . . . . 105.3(3) ?
    C7 S N C2 . . . . -9.8(3) yes
    S N C2 C1 . . . . 173.9(3) ?
    S N C2 C3 . . . . -1.6(5) yes
    C6 C1 C2 N . . . . -179.8(4) ?
    Br C1 C2 N . . . . 54.8(5) yes
    C6 C1 C2 C3 . . . . -3.7(4) ?
    Br C1 C2 C3 . . . . -129.1(3) ?
    N C2 C3 C7 . . . . 14.9(5) yes
    C1 C2 C3 C7 . . . . -161.5(4) ?
    N C2 C3 C4 . . . . -110.4(5) ?
    C1 C2 C3 C4 . . . . 73.2(4) ?
    N C2 C3 C8 . . . . 143.4(4) ?
    C1 C2 C3 C8 . . . . -33.0(5) ?
    C7 C3 C4 C5 . . . . 172.9(5) ?
    C2 C3 C4 C5 . . . . -70.3(5) ?
    C8 C3 C4 C5 . . . . 33.4(5) ?
    C3 C4 C5 C6 . . . . 2.3(7) ?
    C2 C1 C6 C5 . . . . -67.8(5) ?
    Br C1 C6 C5 . . . . 55.6(5) ?
    C2 C1 C6 C8 . . . . 38.6(4) ?
    Br C1 C6 C8 . . . . 162.0(3) ?
    C4 C5 C6 C1 . . . . 68.9(6) ?
    C4 C5 C6 C8 . . . . -36.5(6) ?
    C2 C3 C7 S . . . . -18.6(4) yes
    C4 C3 C7 S . . . . 97.2(4) ?
    C8 C3 C7 S . . . . -131.8(4) ?
    O2 S C7 C3 . . . . 130.3(4) ?
    O1 S C7 C3 . . . . -95.2(4) ?
    N S C7 C3 . . . . 17.4(3) yes
    C7 C3 C8 C9 . . . . 50.5(6) ?
    C2 C3 C8 C9 . . . . -65.6(5) ?
    C4 C3 C8 C9 . . . . -172.5(5) ?
    C7 C3 C8 C10 . . . . -71.8(7) ?
    C2 C3 C8 C10 . . . . 172.1(5) ?
    C4 C3 C8 C10 . . . . 65.2(7) ?
    C7 C3 C8 C6 . . . . 169.6(4) ?
    C2 C3 C8 C6 . . . . 53.5(4) ?
    C4 C3 C8 C6 . . . . -53.4(4) ?
    C1 C6 C8 C9 . . . . 60.2(5) ?
    C5 C6 C8 C9 . . . . 172.0(5) ?
    C1 C6 C8 C10 . . . . -174.7(4) ?
    C5 C6 C8 C10 . . . . -62.9(6) ?
    C1 C6 C8 C3 . . . . -57.2(4) ?
    C5 C6 C8 C3 . . . . 54.6(5) ?
data_global
_journal_date_recd_electronic     2001-08-07
_journal_date_accepted     2001-08-20
_journal_name_full     'Acta Crystallographica, Section E'
_journal_year     2001
_journal_volume     57
_journal_issue      9
_journal_page_first     o886
_journal_page_last     o887
_journal_paper_category     EO
_publ_contact_author
;
Frank R. Fronczek
Department of Chemistry
Louisiana State University
Baton Rouge
LA 70803-1804
USA
;
_publ_contact_author_email     fronz@chxray.chem.lsu.edu
_publ_contact_author_phone     '(225) 578 8270'
_publ_section_title
;
(7-endo-Bromocamphorylsulfonyl)imine
;
loop_
    _publ_author_name
    _publ_author_address
    'Fronczek, Frank R.'
;
     Department of Chemistry
     Louisiana State University
     Baton Rouge
     LA 70803-1804
     USA
;
    'Garcia, J. Gabriel'
;
     Lawrence Berkeley Laboratory
     University of California, Berkeley
     Berkeley
     CA 94720
     USA
;
