Supplementary Material (ESI) for Perkin Transactions
This journal is © The Royal Society of Chemistry 2002


data_9913uj

_database_code_CSD	178166

#------------------ TITLE AND AUTHOR LIST------------------------------------#

_journal_coden_Cambridge      207

loop_
_publ_author_name
_publ_author_address
'Kurtan, Tibor'
;
Department of Organic Chemsitry
University of Debrecen
Debrecen H-4010
Hungary
;
'Baitz-Gacs, Eszter'
;
Institute of Chemsitry
C.R.C., HUngarian Academy of Sciences
Budapest H-1515
Hungary
;
'Majer, Zsuzsa'
;
Institute of Organic Chemsitry
L. Eotvos University
Budapest H-1518
Hungary
;
'Benyei, Attila'
;
Department of Chemistry
Laboratory for X-ray Diffraction
University of Debrecen
Debrecen H-4010
Hungary
;
'Antus, Sandor'
;
Department of Organic Chemsitry
University of Debrecen
Debrecen H-4010
Hungary
;

_publ_contact_author_name      'Dr Sandor Antus'
_publ_contact_author_address
;
Department of Organic Chemistry
University of Debrecen
P.O.B. 20
Debrecen
H-4010
HUNGARY
;
_publ_contact_author_email       ANTUSS@TIGRIS.KLTE.HU
_publ_contact_author_fax         '36(52)512915'
_publ_contact_author_phone       '36(52)512900'
_publ_requested_journal          'J. Chem. Soc. Perkin Trans. 1.'
_publ_requested_coeditor_name    ?
_publ_contact_letter           
;
Date of submission 2001-06-06

Please consider this CIF as supplement to our paper submitted to
J. Chem. Soc. Perkin Trans. 1.
;
_publ_requested_category        ?

_publ_section_title
;
Resolution and configurational assignment of 2H-3,4,5,6-tetrahydro-
2-methyl-2,6-methano-1-benzoxacine derivatives
;

_publ_section_title_footnote
;
?
;

_publ_section_references
;
Altomare, A., Cascarano, G., Giacovazzo, C. & Guagliardi, A.
(1993) J. Appl. Cryst. 26, 343-350.

Enraf-Nonius (1996). MACH3 for PC Ver. 2.0 Software. Enraf-Nonius, Delft,
The Netherlands.

Farrugia, L. J. (1999) WinGX, J. Appl. Cryst. 32, In the press.

Harms, K. & Wocadlo, S. (1995) XCAD-4. Program for Processing CAD-4
Diffractometer Data. University of Marburg, Germany.

Orpen, A. G., Brammer, L., Allen, F. H., Kennard, O., Watson, D. G.,
& Taylor, R. (1992). International Tables for Crystallography,
Volume C.

Sheldrick, G.M. (1997) SHELXL97. Program for crystal structure
refinement. University of Gottingen, Germany.

Spek, A.L. (1990). Acta Cryst. A46, C34

Wilson, A.J.C. (1992) Ed. International Tables for Crystallography,
Volume C, Kluwer Academic Publishers, Dordrecht, The Netherlands.
;
_publ_section_figure_captions
;
Figure 1. View of (+9a) 40% probability displacement ellipsoids)
;
_publ_section_acknowledgements
;
Financial support from Hungarian Research Fund (OTKA)
Grant No. D25136, as well as Bolyai postdoctoral fellowship from the
Hungarian Academy of Sciences for A.C.B is gratefully acknowledged.
;
_publ_section_table_legends
;
Table 1. Fractional atomic coordinates and equivalent
isotropic displacement parameters (\%A^2^)

Table 2. Selected geometric parameters (\%A ,\% )
;
#------------------ AUDIT DETAILS -------------------------------------------#

_audit_creation_date            2001-06-05
_audit_creation_method          'WinGX routine CIF_UPDATE'
_audit_conform_dict_name        cif_core.dic
_audit_conform_dict_version     2.1
_audit_conform_dict_location    ftp://ftp.iucr.org/pub/cif_core.dic
_audit_update_record            ?

_computing_data_collection              'MACH3 for PC (Enraf Nonius, 1996)'
_computing_cell_refinement              'MACH3 for PC (Enraf Nonius, 1996)'



_audit_creation_date            2001-06-05T09:39:42-00:00
_audit_creation_method         'WinGX routine CIF_UPDATE'

#------------------ CHEMICAL INFORMATION ------------------------------------#

_chemical_formula_moiety                'C17 H22 O3'
_chemical_formula_sum                   'C17 H22 O3'
_chemical_formula_weight                274.35

#------------------ UNIT CELL INFORMATION -----------------------------------#

_symmetry_cell_setting                  orthorhombic
_symmetry_space_group_name_H-M          'P 21 21 21'
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                          6.0620(10)
_cell_length_b                          15.1125(10)
_cell_length_c                          16.9916(10)
_cell_angle_alpha                       90
_cell_angle_beta                        90
_cell_angle_gamma                       90
_cell_volume                            1556.6(3)
_cell_formula_units_Z                   4
_cell_measurement_temperature           293(2)
_cell_measurement_reflns_used           25
_cell_measurement_theta_min             10.27
_cell_measurement_theta_max             14.49

#------------------ CRYSTAL INFORMATION -------------------------------------#

_exptl_crystal_description              prism
_exptl_crystal_colour                   colourless
_exptl_crystal_size_max                 0.42
_exptl_crystal_size_mid                 0.3
_exptl_crystal_size_min                 0.22
_exptl_crystal_density_diffrn           1.171
_exptl_absorpt_correction_type          none
_exptl_crystal_density_method           'not measured'
_exptl_crystal_F_000                    592
_exptl_absorpt_coefficient_mu           0.079

#------------------ DATA COLLECTION INFORMATION -----------------------------#

_diffrn_radiation_wavelength            0.71073
_diffrn_radiation_type                  MoK\a
_diffrn_radiation_probe                 x-ray
_diffrn_measurement_device_type         'Enraf Nonius MACH3'
_diffrn_measurement_device              '\k-geometry diffractometer'
_diffrn_measurement_method              'non-profiled omega/2theta scans'
_diffrn_standards_number                3
_diffrn_standards_interval_count        46
_diffrn_standards_interval_time         30
_diffrn_standards_decay_%               4
loop_
_diffrn_standard_refln_index_h
_diffrn_standard_refln_index_k
_diffrn_standard_refln_index_l
0 10 0
2 6 4
-1 -1 8

_diffrn_reflns_number                   2047
_diffrn_reflns_av_R_equivalents         0
_diffrn_reflns_limit_h_min              0
_diffrn_reflns_limit_h_max              7
_diffrn_reflns_limit_k_min              0
_diffrn_reflns_limit_k_max              18
_diffrn_reflns_limit_l_min              -1
_diffrn_reflns_limit_l_max              20
_diffrn_reflns_theta_min                2.7
_diffrn_reflns_theta_max                26.96
_diffrn_reflns_theta_full               26.96
_diffrn_measured_fraction_theta_max	0.99
_diffrn_measured_fraction_theta_full	0.99
_reflns_number_total                    2047
_reflns_number_gt                       1041
_reflns_threshold_expression            >2sigma(I)

#------------------ COMPUTER PROGRAMS USED ----------------------------------#
_computing_data_reduction               'XCAD4 (Harms & Wocadlo, 1995)'
_computing_structure_solution           'SIR-92 (Altomare, 1993)'
_computing_structure_refinement         'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics           'Ortep-3 for Windows (Farrugia, 1997)'
_computing_publication_material
'WinGX publication routines (Farrugia, 1998)'

#------------------ REFINEMENT INFORMATION ----------------------------------#

_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^)+(0.0650P)^2^+0.0272P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_hydrogen_treatment           mixed
_refine_ls_extinction_method            SHELXL
_refine_ls_extinction_expression
Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_extinction_coef              0.022(3)
_refine_ls_number_reflns                2047
_refine_ls_number_parameters            182
_refine_ls_number_restraints            0
_refine_ls_R_factor_gt                  0.0501
_refine_ls_wR_factor_ref                0.1335
_refine_ls_goodness_of_fit_ref          1.02
_refine_ls_restrained_S_all             1.02
_refine_ls_shift/su_max                 0
_refine_ls_abs_structure_details
'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack          3(3)
_refine_diff_density_max                0.104
_refine_diff_density_min                -0.121

#------------------ ATOMIC TYPES, COORDINATES AND THERMAL PARAMETERS --------#

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 0 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.006 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

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_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_group
_atom_site_disorder_assembly
C2 C 0.3795(7) 0.3390(2) 0.35464(19) 0.0683(10) Uani 1 d . . .
C2' C 0.2691(7) 0.0421(2) 0.3358(3) 0.0807(11) Uani 1 d . . .
H2' H 0.4085 0.0179 0.3161 0.097 Uiso 1 calc R . .
C3' C 0.2648(10) 0.0356(3) 0.4245(3) 0.1017(15) Uani 1 d . . .
H3' H 0.1113 0.0348 0.4426 0.122 Uiso 1 calc R . .
C3 C 0.3068(6) 0.26319(19) 0.4078(2) 0.0660(9) Uani 1 d . . .
H3A H 0.3525 0.2764 0.4612 0.079 Uiso 1 calc R . .
H3B H 0.1469 0.2604 0.4074 0.079 Uiso 1 calc R . .
C4 C 0.3965(7) 0.1727(2) 0.38535(19) 0.0639(9) Uani 1 d . . .
C5 C 0.6395(7) 0.1761(3) 0.3646(2) 0.0806(11) Uani 1 d . . .
H5A H 0.6819 0.1204 0.3407 0.097 Uiso 1 calc R . .
H5B H 0.7246 0.1831 0.4126 0.097 Uiso 1 calc R . .
C10A C 0.3813(7) 0.2825(2) 0.2203(2) 0.0651(9) Uani 1 d . . .
C6 C 0.6964(6) 0.2515(3) 0.3084(2) 0.0764(11) Uani 1 d . . .
H6 H 0.8563 0.2525 0.3001 0.092 Uiso 1 calc R . .
C7 C 0.6710(7) 0.1954(3) 0.1689(3) 0.0906(13) Uani 1 d . . .
H7 H 0.8075 0.1682 0.1752 0.109 Uiso 1 calc . . .
C7A C 0.5840(6) 0.2433(2) 0.2306(2) 0.0678(10) Uani 1 d . . .
C8 C 0.5627(11) 0.1865(3) 0.0985(3) 0.0988(15) Uani 1 d . . .
H8 H 0.6245 0.1538 0.0577 0.119 Uiso 1 calc . . .
C9 C 0.3602(11) 0.2271(3) 0.0892(2) 0.0959(15) Uani 1 d . . .
H9 H 0.2851 0.2218 0.0417 0.115 Uiso 1 calc . . .
C10 C 0.2691(8) 0.2751(2) 0.1494(2) 0.0794(11) Uani 1 d . . .
H10 H 0.133 0.3025 0.1428 0.095 Uiso 1 calc . . .
C11 C 0.6255(7) 0.3387(3) 0.3458(2) 0.0844(13) Uani 1 d . . .
H11A H 0.6947 0.3453 0.3969 0.101 Uiso 1 calc R . .
H11B H 0.6713 0.3878 0.3128 0.101 Uiso 1 calc R . .
C12 C 0.2897(9) 0.4259(2) 0.3859(2) 0.0953(14) Uani 1 d . . .
H12A H 0.1321 0.4221 0.3905 0.143 Uiso 1 calc R . .
H12B H 0.3275 0.4729 0.3503 0.143 Uiso 1 calc R . .
H12C H 0.3526 0.4378 0.4367 0.143 Uiso 1 calc R . .
C13 C 0.3846(16) -0.0442(3) 0.4575(3) 0.175(3) Uani 1 d . . .
H13A H 0.3725 -0.0443 0.5138 0.263 Uiso 1 calc R . .
H13B H 0.5373 -0.0416 0.4428 0.263 Uiso 1 calc R . .
H13C H 0.3198 -0.0972 0.4368 0.263 Uiso 1 calc R . .
C14 C 0.0813(9) 0.0020(2) 0.2914(3) 0.1185(19) Uani 1 d . . .
H14A H 0.1054 0.0093 0.2359 0.178 Uiso 1 calc R . .
H14B H -0.0536 0.0309 0.3061 0.178 Uiso 1 calc R . .
H14C H 0.0714 -0.0599 0.3036 0.178 Uiso 1 calc R . .
O1 O 0.2744(5) 0.33028(14) 0.27785(14) 0.0736(7) Uani 1 d . . .
O1' O 0.2668(4) 0.13657(14) 0.32478(14) 0.0700(7) Uani 1 d . . .
O4' O 0.3693(6) 0.11503(16) 0.45167(14) 0.0957(10) Uani 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
C2 0.085(3) 0.062(2) 0.0579(19) -0.0012(17) -0.016(2) -0.016(2)
C2' 0.084(3) 0.056(2) 0.102(3) -0.003(2) 0.027(3) 0.004(2)
C3' 0.136(4) 0.073(3) 0.096(3) 0.010(2) 0.040(3) -0.005(3)
C3 0.069(2) 0.067(2) 0.062(2) -0.0023(17) 0.0089(19) -0.0042(19)
C4 0.076(3) 0.065(2) 0.0505(17) 0.0065(18) 0.003(2) 0.003(2)
C5 0.071(3) 0.108(3) 0.063(2) 0.003(2) -0.006(2) 0.016(2)
C10A 0.080(3) 0.0588(19) 0.056(2) 0.0053(17) -0.012(2) -0.015(2)
C6 0.0484(19) 0.117(3) 0.064(2) 0.005(2) -0.0012(18) -0.011(2)
C7 0.092(3) 0.108(3) 0.072(2) 0.011(2) 0.011(3) 0.000(3)
C7A 0.059(2) 0.087(2) 0.058(2) 0.011(2) 0.004(2) -0.015(2)
C8 0.146(5) 0.083(3) 0.067(3) 0.002(2) 0.019(3) -0.003(3)
C9 0.159(5) 0.066(2) 0.063(2) 0.004(2) -0.024(3) -0.010(3)
C10 0.106(3) 0.062(2) 0.070(2) 0.0001(19) -0.030(3) 0.003(2)
C11 0.079(3) 0.109(3) 0.065(2) 0.006(2) -0.008(2) -0.044(3)
C12 0.134(4) 0.058(2) 0.094(3) -0.015(2) -0.014(3) -0.007(2)
C13 0.326(9) 0.071(3) 0.128(4) 0.028(3) 0.008(7) 0.019(5)
C14 0.091(3) 0.082(3) 0.182(5) -0.055(3) 0.029(4) -0.016(2)
O1 0.0843(16) 0.0691(14) 0.0675(15) -0.0011(13) -0.0125(16) 0.0005(14)
O1' 0.0773(16) 0.0621(13) 0.0707(15) -0.0076(12) 0.0059(14) -0.0018(14)
O4' 0.153(3) 0.0691(16) 0.0653(14) 0.0121(13) 0.014(2) 0.0020(19)


#------------------ MOLECULAR GEOMETRY --------------------------------------#

_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
C2 O1 1.458(4) . ?
C2 C11 1.499(6) . ?
C2 C12 1.518(5) . ?
C2 C3 1.524(4) . ?
C2' O1' 1.441(4) . ?
C2' C14 1.494(6) . ?
C2' C3' 1.510(6) . ?
C3' O4' 1.433(5) . ?
C3' C13 1.515(7) . ?
C3 C4 1.520(4) . ?
C4 O1' 1.405(4) . ?
C4 O4' 1.434(4) . ?
C4 C5 1.516(6) . ?
C5 C6 1.525(5) . ?
C10A C7A 1.376(6) . ?
C10A O1 1.378(4) . ?
C10A C10 1.388(5) . ?
C6 C7A 1.492(5) . ?
C6 C11 1.525(5) . ?
C7 C8 1.371(6) . ?
C7 C7A 1.380(5) . ?
C8 C9 1.381(7) . ?
C9 C10 1.370(6) . ?

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
O1 C2 C11 110.2(3) . . ?
O1 C2 C12 103.6(3) . . ?
C11 C2 C12 113.2(4) . . ?
O1 C2 C3 109.6(3) . . ?
C11 C2 C3 110.2(3) . . ?
C12 C2 C3 109.8(3) . . ?
O1' C2' C14 109.2(3) . . ?
O1' C2' C3' 101.2(3) . . ?
C14 C2' C3' 117.7(4) . . ?
O4' C3' C2' 105.1(3) . . ?
O4' C3' C13 109.6(5) . . ?
C2' C3' C13 114.3(4) . . ?
C4 C3 C2 115.1(3) . . ?
O1' C4 O4' 106.0(3) . . ?
O1' C4 C5 112.8(3) . . ?
O4' C4 C5 108.3(3) . . ?
O1' C4 C3 109.5(3) . . ?
O4' C4 C3 108.0(3) . . ?
C5 C4 C3 112.0(3) . . ?
C4 C5 C6 113.0(3) . . ?
C7A C10A O1 123.7(3) . . ?
C7A C10A C10 120.9(4) . . ?
O1 C10A C10 115.3(4) . . ?
C7A C6 C11 108.2(3) . . ?
C7A C6 C5 113.0(3) . . ?
C11 C6 C5 108.7(3) . . ?
C8 C7 C7A 122.1(4) . . ?
C10A C7A C7 118.0(4) . . ?
C10A C7A C6 119.0(4) . . ?
C7 C7A C6 122.9(4) . . ?
C7 C8 C9 118.8(4) . . ?
C10 C9 C8 120.5(4) . . ?
C9 C10 C10A 119.6(4) . . ?
C2 C11 C6 108.9(3) . . ?
C10A O1 C2 118.5(3) . . ?
C4 O1' C2' 106.5(3) . . ?
C3' O4' C4 107.9(3) . . ?