data_CRYSTALS_cif
_database_code_CSD                  168194
_journal_coden_Cambridge       207
_audit_creation_date        98-11-06
_audit_creation_method      CRYSTALS
#  CKPAUG98
#****************************************************************************
# The contents of this file between this point and the next #***** line
# are held in the file CRYSTALS\SCRIPT\REF.CIF
# This is a character file which you may edit to reflect local
# conditions
#
# 1. SUBMISSION DETAILS
_publ_contact_author
;
Dr David M. Hodgson
Dyson Perrins Laboratory
Oxford University
South Parks Road
Oxford
OX1 3QY
UNITED KINGDOM

Email : DAVID.HODGSON@CHEM.OX.AC.UK
;

_publ_contact_author_email        ' DAVID.HODGSON@CHEM.OX.AC.UK '
_publ_requested_journal           'Perkin Transactions 1'
_publ_requested_coeditor_name                   ?
_publ_contact_letter
;
Please consider this CIF submission for publication as a Short Format
Paper.  The figures have been sent by mail.
;
#=============================================================================
# 2. PROCESSING SUMMARY (IUCr Office Use Only)

_journal_coden_ASTM               ?
_journal_name_full                ?
_journal_year                     ?
_journal_volume                   ?
_journal_issue                    ?
_journal_page_first               ?
_journal_page_last                ?
_journal_suppl_publ_number        ?
_journal_suppl_publ_pages         ?
#=============================================================================
# 3. TITLE AND AUTHOR LIST
_publ_section_title
;
6-substituted 2-azabicyclo[2.2.1]hept-5-enes by nitrogen directed
radical rearrangement: synthesis of an epibatidine analogue with high
binding affinity at the nicotinic acetylcholine receptor
;

loop_
_publ_author_name
'Carpenter, Kate J.'
'Dickenson, Anthony H.'
'Hodgson, David M.'
'Matthews, Ian R.'
'Maxwell, Christopher R.'
'Wisedale, Richard'

#==============================================================================
# 4. TEXT
_publ_section_abstract  #Text of the abstract
;
?
;
_publ_section_comment  #Text of the paper
;
?
;
_publ_section_exptl_prep
;
?
;
_publ_section_exptl_refinement
;
?
;
_publ_section_references
;

Sheldrick, G.M. (1986).  SHELXS86. Program for the solution of
crystal structures.  Univ. of Gottingen, Federal Republic of Germany.

Altomare, A., Cascarano, G., Giacovazzo G., Guagliardi A., Burla M.C.,
Polidori, G.  & Camalli, M. (1994) SIR92 - a program for automatic solution of
crystal structures by direct methods. J. Appl. Cryst. (27), 435

Carruthers, J.R. and Watkin, D.J. (1979), (Chebychev Weighting)
Acta Cryst, A35, 698-699

Watkin, D.J., Prout, C.K. Carruthers, R.J. & Betteridge, P. (1996) CRYSTALS
Issue 10. Chemical Crystallography Laboratory, OXFORD, UK.

Watkin, D.J., Prout, C.K. & Pearce, L.J. (1996) CAMERON, Chemical
Crystallography Laboratory, OXFORD, UK.

Otwinowski, Z. & Minor, W. (1996) DENZO - Processing of X-ray Diffraction
data collected in oscillation mode. Methods in Enzymology (276).

;
_publ_section_figure_captions
;
?
;
_publ_section_acknowledgements
;
?
;
#==========================================================================
# Now, all the strucure specific goodies
#==========================================================================
_computing_data_collection 'DIP2000 software (Enraf-Nonius)'
_computing_cell_refinement 'DENZO (Otwinowski & Minor, 1996)'
_computing_data_reduction
;
DENZO (Otwinowski & Minor, 1996)
;
_computing_structure_refinement
;
CRYSTALS Issue 10 (Watkin, Prout, Carruthers & Betteridge, 1996)
;
_computing_publication_material
;
CRYSTALS Issue 10 (Watkin, Prout, Carruthers & Betteridge, 1996)
;
_computing_molecular_graphics
;
CAMERON (Watkin, Prout & Pearce,  1996)
;
# _computing_structure_solution 'SHELXS86 (Sheldrick, 1986)'
_computing_structure_solution 'SIR92 (Giacovazzo et al, 1992)'

#==========================================================================
# NOW THE GOODIES TO BE ENTERED BY HAND
#==========================================================================

_chemical_melting_point                    ?
_diffrn_radiation_monochromator      graphite
_diffrn_measurement_device     '  Enraf-nonius DIP2020 '
_refine_ls_matrix_type                   full
_refine_ls_weighting_scheme
;
Chebychev polynomial (Carruthers & Watkin, 1979)
;
_atom_sites_solution_primary   Direct_Methods
_atom_sites_solution_hydrogens   Geometric
_refine_ls_hydrogen_treatment   noref
#****************************************************************************
_chemical_name_systematic
;
# IUPAC name, in full
?
;
_cell_length_a 6.225(1)
_cell_angle_alpha 85.74(1)
_cell_length_b 10.446(1)
_cell_angle_beta  87.21(1)
_cell_length_c 12.497(2)
_cell_angle_gamma 83.12(1)
_cell_volume   803.84
_symmetry_cell_setting 'Triclinic '
_symmetry_space_group_name_H-M 'P -1 '
loop_
_symmetry_equiv_pos_as_xyz
'x,y,z'
'-x,-y,-z'
loop_
_atom_type_symbol
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_Cromer_Mann_a1
_atom_type_scat_Cromer_Mann_b1
_atom_type_scat_Cromer_Mann_a2
_atom_type_scat_Cromer_Mann_b2
_atom_type_scat_Cromer_Mann_a3
_atom_type_scat_Cromer_Mann_b3
_atom_type_scat_Cromer_Mann_a4
_atom_type_scat_Cromer_Mann_b4
_atom_type_scat_Cromer_Mann_c
_atom_type_scat_source
'C   '    0.0170    0.0090    2.3100   20.8439
1.0200   10.2075    1.5886    0.5687    0.8650   51.6512    0.2156
'International_Tables_Vol_IV_Table_2.2B'
'H   '    0.0000    0.0000    0.4930   10.5109
0.3229   26.1257    0.1402    3.1424    0.0408   57.7997    0.0030
'International_Tables_Vol_IV_Table_2.2B'
'N   '    0.0290    0.0180   12.2126    0.0057
3.1322    9.8933    2.0125   28.9975    1.1663    0.5826  -11.5290
'International_Tables_Vol_IV_Table_2.2B'
'O   '    0.0470    0.0320    3.0485   13.2771
2.2868    5.7011    1.5463    0.3239    0.8670   32.9089    0.2508
'International_Tables_Vol_IV_Table_2.2B'
'Cl  '    0.3480    0.7020   11.4604    0.0104
7.1964    1.1662    6.2556   18.5194    1.6455   47.7784   -9.5574
'International_Tables_Vol_IV_Table_2.2B'

_chemical_formula_sum ' C16 H21 Cl1 N2 O2 '
_chemical_formula_moiety ' C16 H21 Cl1 N2 O2 '
_chemical_compound_source
;
?
;
_chemical_formula_weight   308.81
_cell_measurement_reflns_used       25
_cell_measurement_theta_min       21
_cell_measurement_theta_max       43
_cell_measurement_temperature      295
_cell_formula_units_Z     2.00
_exptl_crystal_description ' needle '
_exptl_crystal_colour ' colourless '
_exptl_crystal_size_min 0.25
_exptl_crystal_size_mid 0.25
_exptl_crystal_size_max 1.00
_exptl_crystal_density_diffrn 1.28
_exptl_crystal_density_meas ?
_exptl_crystal_F_000 329.50
_exptl_absorpt_coefficient_mu 2.17
_exptl_absorpt_correction_type psi-scan
_exptl_absorpt_process_details '\y scan,(North et al, 1968)'
_exptl_absorpt_correction_T_min 0.97
_exptl_absorpt_correction_T_max 1.00
_diffrn_standards_interval_time ?
_diffrn_standards_interval_count ?
_diffrn_standards_number 3
_diffrn_standards_decay_% 1.67
_diffrn_ambient_temperature        295
_diffrn_reflns_number 3474
_reflns_number_total 3165
_diffrn_reflns_av_R_equivalents 0.01
_reflns_number_observed 2841
_diffrn_reflns_theta_min 3.55
_diffrn_reflns_theta_max 71.91
_diffrn_reflns_limit_h_min 0
_diffrn_reflns_limit_h_max 7
_diffrn_reflns_limit_k_min -12
_diffrn_reflns_limit_k_max 12
_diffrn_reflns_limit_l_min -15
_diffrn_reflns_limit_l_max 15
_reflns_limit_h_min -7
_reflns_limit_h_max 7
_reflns_limit_k_min -12
_reflns_limit_k_max 12
_reflns_limit_l_min 0
_reflns_limit_l_max 15
_reflns_observed_criterion  >3.00\s(I)
_refine_diff_density_min -0.60
_refine_diff_density_max 0.67
_refine_ls_number_reflns 2841
_refine_ls_number_parameters 275
_refine_ls_R_factor_obs 0.0597
_refine_ls_wR_factor_obs 0.0643
_refine_ls_goodness_of_fit_obs 1.0912
_refine_ls_shift/esd_max 0.034739
_refine_ls_abs_structure_details ' from Flack enantiopole 0.000'
_refine_ls_structure_factor_coef F
_diffrn_radiation_type       'Cu K\a'
_diffrn_radiation_wavelength      1.54180
_diffrn_measurement_method 2\q/\w

loop_
_atom_site_label
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z

# Uequiv = arithmetic mean of Ui
# i.e. Ueqiv = (U1+U2+U3)/3
_atom_site_U_iso_or_equiv
_atom_site_occupancy
_atom_site_thermal_displace_type
CL1 0.2021(1) 0.87647(6) -0.09780(5) 0.0958 1.0000 Uani
C102 0.1543(3) 0.7478(2) -0.0055(1) 0.0617 1.0000 Uani
N101 0.3230(3) 0.6622(2) 0.0132(1) 0.0695 1.0000 Uani
C106 0.2912(3) 0.5633(2) 0.0847(1) 0.0625 1.0000 Uani
C105 0.0959(2) 0.5467(1) 0.1380(1) 0.0486 1.0000 Uani
C6 0.0669(3) 0.4376(2) 0.2214(1) 0.0506 1.0000 Uani
C1 0.0923(2) 0.4748(1) 0.3373(1) 0.0476 1.0000 Uani
N2 0.3125(2) 0.5094(1) 0.3440(1) 0.0492 1.0000 Uani
C201 0.3795(2) 0.6268(1) 0.3418(1) 0.0481 1.0000 Uani
O1 0.2100(2) 0.7196(1) 0.3396(1) 0.0538 1.0000 Uani
C202 0.2421(3) 0.8568(1) 0.3345(1) 0.0534 1.0000 Uani
C205 0.3515(4) 0.8861(2) 0.4341(2) 0.0712 1.0000 Uani
C203 0.0106(4) 0.9215(2) 0.3340(2) 0.0765 1.0000 Uani
C204 0.3672(5) 0.8941(2) 0.2327(2) 0.0759 1.0000 Uani
O2 0.5710(2) 0.6441(1) 0.3427(1) 0.0675 1.0000 Uani
C3 0.4674(3) 0.3912(2) 0.3442(2) 0.0610 1.0000 Uani
C4 0.3130(3) 0.2907(2) 0.3311(1) 0.0591 1.0000 Uani
C7 0.1165(3) 0.3422(2) 0.3991(1) 0.0619 1.0000 Uani
C5 0.2280(3) 0.3108(2) 0.2175(1) 0.0606 1.0000 Uani
C104 -0.0760(3) 0.6407(2) 0.1147(1) 0.0602 1.0000 Uani
C103 -0.0476(3) 0.7435(2) 0.0417(2) 0.0679 1.0000 Uani
H301 0.140(4) 0.348(2) 0.471(2) 0.072(6) 1.0000 Uiso
H302 -0.011(3) 0.541(2) 0.362(1) 0.053(5) 1.0000 Uiso
H303 0.375(4) 0.201(2) 0.350(2) 0.069(6) 1.0000 Uiso
H304 0.567(4) 0.397(2) 0.284(2) 0.066(6) 1.0000 Uiso
H305 0.337(4) 0.982(3) 0.438(2) 0.083(7) 1.0000 Uiso
H306 0.160(3) 0.238(2) 0.203(2) 0.064(5) 1.0000 Uiso
H307 0.305(4) 0.870(2) 0.172(2) 0.086(7) 1.0000 Uiso
H308 -0.015(4) 0.295(2) 0.396(2) 0.069(6) 1.0000 Uiso
H309 -0.081(4) 0.416(2) 0.218(2) 0.067(5) 1.0000 Uiso
H310 0.003(5) 1.018(3) 0.330(2) 0.098(8) 1.0000 Uiso
H311 0.355(4) 0.319(2) 0.162(2) 0.065(5) 1.0000 Uiso
H312 0.281(5) 0.857(3) 0.504(3) 0.104(9) 1.0000 Uiso
H313 0.369(4) 0.989(2) 0.225(2) 0.078(6) 1.0000 Uiso
H314 -0.048(5) 0.898(3) 0.272(2) 0.091(8) 1.0000 Uiso
H315 0.538(4) 0.373(2) 0.414(2) 0.075(6) 1.0000 Uiso
H316 -0.170(4) 0.810(2) 0.022(2) 0.086(7) 1.0000 Uiso
H317 -0.074(5) 0.889(3) 0.400(2) 0.092(8) 1.0000 Uiso
H319 0.416(4) 0.498(2) 0.096(2) 0.080(7) 1.0000 Uiso
H320 0.496(5) 0.846(3) 0.432(2) 0.089(8) 1.0000 Uiso
H322 -0.207(4) 0.635(2) 0.146(2) 0.081(7) 1.0000 Uiso
H323 0.506(5) 0.850(3) 0.225(2) 0.097(8) 1.0000 Uiso
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
CL1 0.1224(5) 0.0746(4) 0.0830(4) 0.0311(3) 0.0021(3) -0.0068(3)
C102 0.078(1) 0.0554(9) 0.0486(8) 0.0055(7) -0.0008(7) -0.0023(8)
N101 0.0684(9) 0.0669(9) 0.0666(9) 0.0137(7) 0.0154(7) 0.0009(7)
C106 0.0573(9) 0.0598(9) 0.0641(9) 0.0107(7) 0.0110(7) 0.0041(7)
C105 0.0510(8) 0.0515(8) 0.0432(7) -0.0048(6) -0.0008(6) -0.0055(6)
C6 0.0497(8) 0.0513(8) 0.0524(8) -0.0031(6) 0.0012(6) -0.0134(6)
C1 0.0441(7) 0.0493(8) 0.0500(7) -0.0013(6) 0.0054(6) -0.0114(6)
N2 0.0423(6) 0.0420(6) 0.0632(7) -0.0012(5) -0.0041(5) -0.0053(5)
C201 0.0446(7) 0.0458(7) 0.0541(8) -0.0020(6) -0.0051(6) -0.0061(5)
O1 0.0457(6) 0.0411(5) 0.0754(7) -0.0059(5) -0.0046(5) -0.0060(4)
C202 0.0629(9) 0.0400(7) 0.0580(8) -0.0020(6) -0.0065(7) -0.0085(6)
C205 0.094(2) 0.054(1) 0.069(1) -0.0082(8) -0.018(1) -0.0144(9)
C203 0.076(1) 0.052(1) 0.099(2) -0.004(1) -0.009(1) 0.0056(9)
C204 0.095(2) 0.064(1) 0.068(1) 0.0027(9) 0.007(1) -0.019(1)
O2 0.0426(6) 0.0612(7) 0.1005(9) -0.0045(6) -0.0115(6) -0.0109(5)
C3 0.0545(9) 0.0464(8) 0.080(1) 0.0030(7) -0.0074(8) 0.0008(7)
C4 0.071(1) 0.0400(8) 0.0644(9) 0.0040(6) -0.0005(8) -0.0063(7)
C7 0.075(1) 0.0559(9) 0.0555(9) 0.0061(7) 0.0056(8) -0.0191(8)
C5 0.078(1) 0.0438(8) 0.0608(9) -0.0058(7) 0.0028(8) -0.0093(7)
C104 0.0499(9) 0.068(1) 0.0608(9) -0.0010(7) -0.0010(7) -0.0003(7)
C103 0.069(1) 0.067(1) 0.063(1) 0.0038(8) -0.0101(8) 0.0094(9)
_refine_ls_extinction_coef 238.8(111)
_refine_ls_extinction_method
'Larson 1970 Crystallographic Computing eq 22'
loop_
_geom_bond_atom_site_label_1
_geom_bond_site_symmetry_1
_geom_bond_atom_site_label_2
_geom_bond_site_symmetry_2
_geom_bond_distance
_geom_bond_publ_flag
CL1 . C102 . 1.749(2)    yes
C102 . N101 . 1.313(3)    yes
C102 . C103 . 1.367(3)    yes
N101 . C106 . 1.341(2)    yes
C106 . C105 . 1.380(2)    yes
C106 . H319 . 0.98(2)    no
C105 . C6 . 1.508(2)    yes
C105 . C104 . 1.389(2)    yes
C6 . C1 . 1.548(2)    yes
C6 . C5 . 1.564(2)    yes
C6 . H309 . 0.98(2)    no
C1 . N2 . 1.467(2)    yes
C1 . C7 . 1.530(2)    yes
C1 . H302 . 0.95(2)    no
N2 . C201 . 1.340(2)    yes
N2 . C3 . 1.473(2)    yes
C201 . O1 . 1.344(2)    yes
C201 . O2 . 1.228(2)    yes
O1 . C202 . 1.467(2)    yes
C202 . C205 . 1.516(2)    yes
C202 . C203 . 1.516(3)    yes
C202 . C204 . 1.510(3)    yes
C205 . H305 . 1.00(3)    no
C205 . H312 . 1.00(3)    no
C205 . H320 . 0.94(3)    no
C203 . H310 . 1.00(3)    no
C203 . H314 . 0.94(3)    no
C203 . H317 . 1.01(3)    no
C204 . H307 . 0.94(3)    no
C204 . H313 . 0.99(2)    no
C204 . H323 . 0.93(3)    no
C3 . C4 . 1.528(3)    yes
C3 . H304 . 0.96(2)    no
C3 . H315 . 0.99(2)    no
C4 . C7 . 1.522(3)    yes
C4 . C5 . 1.530(3)    yes
C4 . H303 . 0.98(2)    no
C7 . H301 . 0.93(2)    no
C7 . H308 . 1.01(2)    no
C5 . H306 . 0.95(2)    no
C5 . H311 . 1.04(2)    no
C104 . C103 . 1.379(3)    yes
C104 . H322 . 0.90(3)    no
C103 . H316 . 0.99(3)    no
loop_
_geom_angle_atom_site_label_1
_geom_angle_site_symmetry_1
_geom_angle_atom_site_label_2
_geom_angle_site_symmetry_2
_geom_angle_atom_site_label_3
_geom_angle_site_symmetry_3
_geom_angle
_geom_angle_publ_flag
CL1 . C102 . N101 . 115.2(1)    yes
CL1 . C102 . C103 . 119.5(1)    yes
N101 . C102 . C103 . 125.3(2)    yes
C102 . N101 . C106 . 116.4(2)    yes
N101 . C106 . C105 . 124.4(2)    yes
N101 . C106 . H319 . 116.0(14)    no
C105 . C106 . H319 . 119.5(14)    no
C106 . C105 . C6 . 123.3(1)    yes
C106 . C105 . C104 . 116.3(2)    yes
C6 . C105 . C104 . 120.3(1)    yes
C105 . C6 . C1 . 113.0(1)    yes
C105 . C6 . C5 . 118.4(1)    yes
C1 . C6 . C5 . 101.4(1)    yes
C105 . C6 . H309 . 107.6(13)    no
C1 . C6 . H309 . 106.9(12)    no
C5 . C6 . H309 . 109.0(12)    no
C6 . C1 . N2 . 107.6(1)    yes
C6 . C1 . C7 . 101.5(1)    yes
N2 . C1 . C7 . 99.9(1)    yes
C6 . C1 . H302 . 115.5(11)    no
N2 . C1 . H302 . 110.9(11)    no
C7 . C1 . H302 . 119.6(11)    no
C1 . N2 . C201 . 129.1(1)    yes
C1 . N2 . C3 . 109.2(1)    yes
C201 . N2 . C3 . 121.5(1)    yes
N2 . C201 . O1 . 110.8(1)    yes
N2 . C201 . O2 . 123.2(1)    yes
O1 . C201 . O2 . 126.0(1)    yes
C201 . O1 . C202 . 121.1(1)    yes
O1 . C202 . C205 . 110.0(1)    yes
O1 . C202 . C203 . 101.7(1)    yes
C205 . C202 . C203 . 110.5(2)    yes
O1 . C202 . C204 . 110.8(1)    yes
C205 . C202 . C204 . 112.1(2)    yes
C203 . C202 . C204 . 111.3(2)    yes
C202 . C205 . H305 . 108.3(14)    no
C202 . C205 . H312 . 115.0(17)    no
H305 . C205 . H312 . 102.6(21)    no
C202 . C205 . H320 . 108.9(16)    no
H305 . C205 . H320 . 114.3(21)    no
H312 . C205 . H320 . 107.9(23)    no
C202 . C203 . H310 . 112.1(17)    no
C202 . C203 . H314 . 105.9(17)    no
H310 . C203 . H314 . 108.1(23)    no
C202 . C203 . H317 . 110.2(16)    no
H310 . C203 . H317 . 110.6(21)    no
H314 . C203 . H317 . 109.8(24)    no
C202 . C204 . H307 . 111.8(16)    no
C202 . C204 . H313 . 109.9(14)    no
H307 . C204 . H313 . 107.6(21)    no
C202 . C204 . H323 . 114.9(18)    no
H307 . C204 . H323 . 100.5(23)    no
H313 . C204 . H323 . 111.7(23)    no
N2 . C3 . C4 . 100.2(1)    yes
N2 . C3 . H304 . 109.2(13)    no
C4 . C3 . H304 . 111.4(12)    no
N2 . C3 . H315 . 111.5(13)    no
C4 . C3 . H315 . 109.6(14)    no
H304 . C3 . H315 . 114.1(19)    no
C3 . C4 . C7 . 101.4(1)    yes
C3 . C4 . C5 . 108.5(1)    yes
C7 . C4 . C5 . 102.2(2)    yes
C3 . C4 . H303 . 114.1(13)    no
C7 . C4 . H303 . 116.1(13)    no
C5 . C4 . H303 . 113.2(13)    no
C1 . C7 . C4 . 93.8(1)    yes
C1 . C7 . H301 . 112.2(14)    no
C4 . C7 . H301 . 115.7(14)    no
C1 . C7 . H308 . 112.7(12)    no
C4 . C7 . H308 . 115.4(12)    no
H301 . C7 . H308 . 106.8(19)    no
C6 . C5 . C4 . 103.6(1)    yes
C6 . C5 . H306 . 113.2(13)    no
C4 . C5 . H306 . 108.7(12)    no
C6 . C5 . H311 . 112.8(11)    no
C4 . C5 . H311 . 110.1(12)    no
H306 . C5 . H311 . 108.3(17)    no
C105 . C104 . C103 . 120.4(2)    yes
C105 . C104 . H322 . 120.6(16)    no
C103 . C104 . H322 . 119.0(16)    no
C102 . C103 . C104 . 117.1(2)    yes
C102 . C103 . H316 . 121.3(15)    no
C104 . C103 . H316 . 121.6(15)    no