#------------------------------------------------------------------------------
#$Date: 2011-09-10 04:16:28 +0100 (Sat, 10 Sep 2011) $
#$Revision: 25271 $
#$URL: svn://www.crystallography.net/cod/cif/2/2011535.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_2011535
loop_
_publ_author_name
'Batsanov, Andrei S.'
'Howard, Judith A. K.'
'O'Hagan, David'
'Tavasli, Mustafa'
_publ_section_title
;
 3\a-Tosyloxymethyltropane(<i>N</i>^8^--<i>B</i>)borane
;
_journal_issue                   11
_journal_name_full               'Acta Crystallographica Section C'
_journal_page_first              e512
_journal_page_last               e513
_journal_volume                  56
_journal_year                    2000
_chemical_formula_sum            'C16 H26 B N O3 S'
_chemical_formula_weight         323.25
_chemical_melting_point          388.3(14)
_chemical_name_systematic
;
3\a-Tosyloxymethyltropane(N^8^---B)--borane
;
_space_group_IT_number           33
_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_Hall  'P 2c -2n'
_symmetry_space_group_name_H-M   'P n a 21'
_audit_creation_method           SHELXL
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   21.443(2)
_cell_length_b                   7.9590(10)
_cell_length_c                   10.224(2)
_cell_measurement_reflns_used    25
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      25.2
_cell_measurement_theta_min      20.5
_cell_volume                     1744.9(4)
_computing_cell_refinement       'MSC/AFC Diffractometer Control Software'
_computing_data_collection
;
MSC/AFC Diffractometer Control Software (Molecular Structure Corporation,
1991)
;
_computing_data_reduction
'TEXSAN (Molecular Structure Corporation, 1989)'
_computing_publication_material  SHELXTL
_computing_structure_refinement  SHELXTL
_computing_structure_solution    'SHELXTL (Bruker, 1997)'
_diffrn_ambient_temperature      293(2)
_diffrn_measurement_device       'Rigaku AFC-6S four-circle'
_diffrn_measurement_method       2\q/\w
_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  .020
_diffrn_reflns_av_sigmaI/netI    .0466
_diffrn_reflns_limit_h_max       26
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -6
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -8
_diffrn_reflns_number            2243
_diffrn_reflns_theta_max         75
_diffrn_reflns_theta_min         4.12
_diffrn_standards_decay_%        .8
_diffrn_standards_interval_count 147
_diffrn_standards_number         3
_exptl_absorpt_coefficient_mu    1.731
_exptl_absorpt_correction_T_max  .837
_exptl_absorpt_correction_T_min  .726
_exptl_absorpt_correction_type   analytical
_exptl_absorpt_process_details   '(de Meulenaer & Tompa, 1965)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.230
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             696
_exptl_crystal_size_max          .28
_exptl_crystal_size_mid          .22
_exptl_crystal_size_min          .11
_refine_diff_density_max         .206
_refine_diff_density_min         -.168
_refine_ls_abs_structure_details 'Flack (1983)'
_refine_ls_abs_structure_Flack   .35(3)
_refine_ls_extinction_coef       .00081(14)
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_all   1.045
_refine_ls_goodness_of_fit_ref   1.091
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     208
_refine_ls_number_reflns         2157
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.044
_refine_ls_restrained_S_obs      1.091
_refine_ls_R_factor_all          .066
_refine_ls_R_factor_gt           .043
_refine_ls_shift/su_max          -.001
_refine_ls_shift/su_mean         .000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w = 1/[\s^2^(Fo^2^)+(0.0473P)^2^+0.4507P] where P = (Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_all         .115
_refine_ls_wR_factor_ref         .103
_reflns_number_gt                1613
_reflns_number_total             2157
_reflns_threshold_expression     I>2\s(I)
_[local]_cod_data_source_file    qa0392.cif
_[local]_cod_data_source_block   I
_cod_depositor_comments
;
The following automatic conversions were performed:

'_chemical_melting_point' value '113.8--116.5 \% C' was changed to
'388.3(14)' - it was converted from degrees Celsius(C) to Kelvins(K),
the average value was taken and precision was
estimated.

'_symmetry_cell_setting' value 'Orthorhombic' changed to
'orthorhombic' according to
/home/saulius/struct/CIF-dictionaries/cif_core.dic dictionary named
'cif_core.dic' version 2.4.1 from 2010-06-29.

Automatic conversion script
Id: cif_fix_values 1715 2011-07-08 13:25:40Z adriana 
;
_cod_database_code               2011535
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, z+1/2'
'x+1/2, -y+1/2, z'
'-x+1/2, y+1/2, z+1/2'
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
S .0494(6) .0530(6) .0534(7) .0071(6) -.0019(7) -.0057(8)
O1 .047(2) .063(2) .054(2) .004(2) -.003(2) -.013(2)
O2 .062(2) .071(2) .063(2) .007(2) .004(2) -.022(2)
O3 .067(2) .055(2) .072(3) .006(2) .001(2) .014(2)
N .050(2) .050(2) .047(3) .003(2) -.001(2) .002(2)
C1 .048(3) .058(3) .041(3) -.005(2) .002(2) .005(3)
C2 .043(2) .053(3) .067(3) -.007(2) -.002(3) .003(3)
C3 .046(2) .056(3) .048(4) -.003(2) -.002(2) -.004(3)
C4 .056(3) .069(3) .041(3) .003(3) .010(3) .000(3)
C5 .062(3) .052(3) .050(4) -.006(2) .011(3) .007(3)
C6 .054(3) .058(3) .073(4) -.007(3) -.004(3) -.012(3)
C7 .061(3) .078(4) .040(3) -.001(3) -.001(3) -.001(3)
C8 .064(3) .095(5) .068(4) .020(3) -.015(3) -.001(4)
C9 .049(3) .058(3) .061(4) .007(2) .008(3) .005(3)
C10 .055(3) .057(4) .136(6) -.003(3) .004(4) -.023(4)
C11 .043(2) .051(3) .048(4) .004(2) -.004(2) -.004(3)
C12 .059(3) .067(4) .050(3) .006(3) .001(3) -.007(3)
C13 .068(4) .064(4) .060(4) .008(3) -.017(3) -.016(3)
C14 .036(3) .064(4) .084(4) .003(3) .000(3) -.016(4)
C15 .060(3) .060(3) .064(4) -.003(3) .005(3) .008(3)
C16 .057(3) .068(4) .049(3) .000(3) -.002(3) -.002(3)
B .084(4) .059(4) .083(5) .019(4) .009(5) .000(4)
loop_
_atom_site_label
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_thermal_displace_type
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_occupancy
_atom_site_type_symbol
S .62305(5) .40959(14) .49106(13) .0519(3) Uani d . 1 S
O1 .55683(14) .4624(4) .4392(3) .0549(9) Uani d . 1 O
O2 .6527(2) .3351(4) .3808(4) .0656(10) Uani d . 1 O
O3 .6162(2) .3152(5) .6094(4) .0647(10) Uani d . 1 O
N .3988(2) .9398(4) .5051(4) .0487(10) Uani d . 1 N
C1 .3977(2) .8095(6) .6114(5) .0490(12) Uani d . 1 C
H1 .3598(2) .8212(6) .6641(5) .059 Uiso d R 1 H
C2 .4024(2) .6322(6) .5566(6) .0543(13) Uani d . 1 C
H21 .3641(2) .6071(6) .5100(6) .071 Uiso d R 1 H
H22 .4055(2) .5540(6) .6290(6) .071 Uiso d R 1 H
C3 .4580(2) .6017(6) .4633(5) .0500(13) Uani d . 1 C
H3 .4436(2) .5223(6) .3966(5) .060 Uiso d R 1 H
C4 .4783(2) .7622(6) .3904(5) .0555(13) Uani d . 1 C
H41 .5225(2) .7541(6) .3716(5) .072 Uiso d R 1 H
H42 .4564(2) .7666(6) .3074(5) .072 Uiso d R 1 H
C5 .4665(2) .9258(6) .4631(5) .0546(14) Uani d . 1 C
H5 .4780(2) 1.0218(6) .4082(5) .066 Uiso d R 1 H
C6 .5006(2) .9343(7) .5936(5) .0615(15) Uani d . 1 C
H61 .5103(2) 1.0496(7) .6165(5) .080 Uiso d R 1 H
H62 .5390(2) .8701(7) .5906(5) .080 Uiso d R 1 H
C7 .4546(3) .8577(7) .6921(5) .0597(14) Uani d . 1 C
H71 .4726(3) .7594(7) .7338(5) .078 Uiso d R 1 H
H72 .4436(3) .9387(7) .7591(5) .078 Uiso d R 1 H
C8 .3543(3) .9034(7) .3959(6) .076(2) Uani d . 1 C
H81 .3609(12) .982(3) .3263(17) .114(14) Uiso d R 1 H
H82 .3122(3) .913(5) .4271(11) .114(14) Uiso d R 1 H
H83 .3612(12) .7914(19) .364(3) .114(14) Uiso d R 1 H
C9 .5105(2) .5163(6) .5362(5) .0560(14) Uani d . 1 C
H91 .5293(2) .5937(6) .5980(5) .073 Uiso d R 1 H
H92 .4948(2) .4200(6) .5841(5) .073 Uiso d R 1 H
C10 .7495(3) 1.0692(7) .6108(7) .082(2) Uani d . 1 C
H101 .7187(4) 1.1483(19) .640(4) .137(16) Uiso d R 1 H
H102 .7693(18) 1.111(3) .5332(13) .137(16) Uiso d R 1 H
H103 .7802(15) 1.0534(14) .678(3) .137(16) Uiso d R 1 H
C11 .6586(2) .6013(6) .5268(5) .0476(12) Uani d . 1 C
C12 .6851(2) .6273(7) .6478(5) .0589(14) Uani d . 1 C
H12 .6829(2) .5447(7) .7120(5) .071 Uiso d R 1 H
C13 .7151(3) .7806(7) .6730(6) .064(2) Uani d . 1 C
H13 .7333(3) .7988(7) .7543(6) .077 Uiso d R 1 H
C14 .7180(2) .9020(8) .5810(6) .0612(15) Uani d . 1 C
C15 .6919(2) .8745(7) .4600(6) .061(2) Uani d . 1 C
H15 .6940(2) .9585(7) .3969(6) .074 Uiso d R 1 H
C16 .6628(2) .7257(7) .4310(5) .0581(14) Uani d . 1 C
H16 .6458(2) .7079(7) .3484(5) .070 Uiso d R 1 H
B .3812(3) 1.1297(9) .5579(8) .075(2) Uani d . 1 B
H1B .4151(12) 1.1668(19) .646(3) .077(9) Uiso d R 1 H
H2B .3286(12) 1.1315(13) .595(3) .077(9) Uiso d R 1 H
H3B .3871(12) 1.228(3) .471(2) .077(9) Uiso d R 1 H
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'
N N .0311 .0180 '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'
S S .3331 .5567 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
B B .0090 .0039 '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
O2 S O3 119.8(2) ?
O2 S O1 104.4(2) ?
O3 S O1 109.4(2) ?
O2 S C11 109.6(2) ?
O3 S C11 109.0(2) ?
O1 S C11 103.4(2) ?
C9 O1 S 117.5(3) ?
C8 N C1 113.3(4) yes
C8 N C5 112.6(4) yes
C1 N C5 99.7(3) yes
C8 N B 106.0(4) yes
C1 N B 113.1(4) yes
C5 N B 112.3(4) yes
N C1 C2 111.9(4) ?
N C1 C7 101.9(4) ?
C2 C1 C7 112.3(4) ?
C1 C2 C3 115.0(4) ?
C9 C3 C4 113.6(4) ?
C9 C3 C2 110.0(4) ?
C4 C3 C2 112.7(4) ?
C5 C4 C3 115.3(4) ?
N C5 C4 111.1(4) ?
N C5 C6 102.0(4) ?
C4 C5 C6 112.7(4) ?
C5 C6 C7 104.4(4) ?
C1 C7 C6 105.0(4) ?
O1 C9 C3 107.7(4) ?
C12 C11 C16 119.9(5) ?
C12 C11 S 120.0(4) ?
C16 C11 S 120.1(4) ?
C11 C12 C13 119.0(5) ?
C14 C13 C12 121.0(5) ?
C13 C14 C15 119.6(5) ?
C13 C14 C10 120.4(6) ?
C15 C14 C10 120.0(6) ?
C16 C15 C14 121.2(5) ?
C15 C16 C11 119.3(5) ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_publ_flag
S O2 1.424(4) yes
S O3 1.432(4) yes
S O1 1.573(3) yes
S C11 1.745(5) yes
O1 C9 1.467(5) yes
N C8 1.497(7) yes
N C1 1.502(6) yes
N C5 1.518(6) yes
N B 1.649(8) yes
C1 C2 1.522(6) yes
C1 C7 1.523(7) yes
C2 C3 1.545(6) yes
C3 C9 1.513(6) yes
C3 C4 1.541(6) yes
C4 C5 1.520(6) yes
C5 C6 1.523(7) yes
C6 C7 1.536(7) yes
C10 C14 1.523(7) ?
C11 C12 1.376(7) ?
C11 C16 1.396(7) ?
C12 C13 1.403(7) ?
C13 C14 1.350(8) ?
C14 C15 1.375(7) ?
C15 C16 1.372(7) ?