# Copyright The Royal Society of Chemistry, 1999
# CCDC Number: 440/111

data_bioc1

_audit_creation_method            SHELXL-97
_chemical_name_systematic
;
 ?
;
_chemical_name_common             ?
_chemical_melting_point           ?
_chemical_formula_moiety          ?
_chemical_formula_sum
 'C15 H17 N O3'
_chemical_formula_weight          259.30

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'

_symmetry_cell_setting            ?
_symmetry_space_group_name_H-M    ?

loop_
 _symmetry_equiv_pos_as_xyz
 'x, y, z'
 '-x, -y, -z'

_cell_length_a                    7.161(2)
_cell_length_b                    8.296(3)
_cell_length_c                    11.377(3)
_cell_angle_alpha                 77.42(3)
_cell_angle_beta                  82.78(3)
_cell_angle_gamma                 68.75(3)
_cell_volume                      614.0(3)
_cell_formula_units_Z             2
_cell_measurement_temperature     293(2)
_cell_measurement_reflns_used     ?
_cell_measurement_theta_min       ?
_cell_measurement_theta_max       ?

_exptl_crystal_description        ?
_exptl_crystal_colour             ?
_exptl_crystal_size_max           ?
_exptl_crystal_size_mid           ?
_exptl_crystal_size_min           ?
_exptl_crystal_density_meas       ?
_exptl_crystal_density_diffrn     1.403
_exptl_crystal_density_method     'not measured'
_exptl_crystal_F_000              276
_exptl_absorpt_coefficient_mu     0.098
_exptl_absorpt_correction_type    ?
_exptl_absorpt_correction_T_min   ?
_exptl_absorpt_correction_T_max   ?
_exptl_absorpt_process_details    ?

_exptl_special_details
;
 ?
;

_diffrn_ambient_temperature       293(2)
_diffrn_radiation_wavelength      0.71073
_diffrn_radiation_type            MoK\a
_diffrn_radiation_source          'fine-focus sealed tube'
_diffrn_radiation_monochromator   graphite
_diffrn_measurement_device_type   ?
_diffrn_measurement_method        ?
_diffrn_detector_area_resol_mean  ?
_diffrn_standards_number          ?
_diffrn_standards_interval_count  ?
_diffrn_standards_interval_time   ?
_diffrn_standards_decay_%         ?
_diffrn_reflns_number             2278
_diffrn_reflns_av_R_equivalents   0.0256
_diffrn_reflns_av_sigmaI/netI     0.0451
_diffrn_reflns_limit_h_min        -8
_diffrn_reflns_limit_h_max        8
_diffrn_reflns_limit_k_min        -9
_diffrn_reflns_limit_k_max        9
_diffrn_reflns_limit_l_min        -13
_diffrn_reflns_limit_l_max        0
_diffrn_reflns_theta_min          2.68
_diffrn_reflns_theta_max          24.97
_reflns_number_total              2157
_reflns_number_gt                 1479
_reflns_threshold_expression      >2sigma(I)

_computing_data_collection        ?
_computing_cell_refinement        ?
_computing_data_reduction         ?
_computing_structure_solution     'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement   'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics     ?
_computing_publication_material   ?

_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^)+(0.0457P)^2^+0.1522P] where P=(Fo^2^+2Fc^2^)/3'
_atom_sites_solution_primary      direct
_atom_sites_solution_secondary    difmap
_atom_sites_solution_hydrogens    geom
_refine_ls_hydrogen_treatment     mixed
_refine_ls_extinction_method      none
_refine_ls_extinction_coef        ?
_refine_ls_number_reflns          2157
_refine_ls_number_parameters      201
_refine_ls_number_restraints      0
_refine_ls_R_factor_all           0.0788
_refine_ls_R_factor_gt            0.0431
_refine_ls_wR_factor_ref          0.1053
_refine_ls_wR_factor_gt           0.0913
_refine_ls_goodness_of_fit_ref    1.042
_refine_ls_restrained_S_all       1.042
_refine_ls_shift/su_max           0.017
_refine_ls_shift/su_mean          0.004

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_multiplicit
 _atom_site_calc_flag
 _atom_site_refinement_flags
 _atom_site_disorder_assembly
 _atom_site_disorder_group
N1 N 0.7008(3) 0.1329(2) 0.12101(16) 0.0267(4) Uani 1 1 d . . .
O1 O 0.6206(3) 0.1770(2) 0.01713(14) 0.0384(4) Uani 1 1 d . . .
C2 C 0.7284(3) -0.0135(3) 0.1978(2) 0.0272(5) Uani 1 1 d . . .
C3 C 0.8302(3) -0.0167(3) 0.3042(2) 0.0291(5) Uani 1 1 d . . .
H3A H 0.971(2) -0.0934(13) 0.3013(2) 0.042(7) Uiso 1 1 calc R . .
H3B H 0.7637(11) -0.0583(8) 0.3792(12) 0.028(6) Uiso 1 1 calc R . .
C3A C 0.8122(3) 0.1759(3) 0.29545(19) 0.0246(5) Uani 1 1 d . . .
C3B C 0.6115(3) 0.2847(3) 0.34545(19) 0.0245(5) Uani 1 1 d . . .
C4 C 0.5177(3) 0.2648(3) 0.4586(2) 0.0302(5) Uani 1 1 d . . .
H4 H 0.5774(15) 0.171(2) 0.5191(15) 0.028(6) Uiso 1 1 calc R . .
C5 C 0.3319(4) 0.3883(3) 0.4788(2) 0.0340(6) Uani 1 1 d . . .
H5 H 0.262(2) 0.3768(5) 0.559(2) 0.054(8) Uiso 1 1 calc R . .
C6 C 0.2436(4) 0.5280(3) 0.3885(2) 0.0333(6) Uani 1 1 d . . .
H6 H 0.118(3) 0.609(2) 0.4046(5) 0.041(7) Uiso 1 1 calc R . .
C7 C 0.3364(3) 0.5508(3) 0.2741(2) 0.0275(5) Uani 1 1 d . . .
O7 O 0.2392(2) 0.6895(2) 0.18981(16) 0.0396(5) Uani 1 1 d . . .
H7 H 0.310(5) 0.706(4) 0.117(3) 0.072(10) Uiso 1 1 d . . .
C7A C 0.5230(3) 0.4251(3) 0.25618(19) 0.0248(5) Uani 1 1 d . . .
O8 O 0.6373(2) 0.42512(18) 0.14852(13) 0.0277(4) Uani 1 1 d . . .
C8A C 0.7867(3) 0.2541(3) 0.15925(19) 0.0247(5) Uani 1 1 d . . .
C9 C 0.9716(3) 0.2572(3) 0.0800(2) 0.0313(6) Uani 1 1 d . . .
H9A H 0.9316(7) 0.3458(15) 0.0074(12) 0.033(6) Uiso 1 1 calc R . .
H9B H 1.0368(11) 0.1434(19) 0.0557(5) 0.044(7) Uiso 1 1 calc R . .
C10 C 1.1214(4) 0.2973(3) 0.1430(2) 0.0388(6) Uani 1 1 d . . .
H10A H 1.246(2) 0.2861(4) 0.0904(9) 0.045(7) Uiso 1 1 calc R . .
H10B H 1.0629(10) 0.420(2) 0.1574(3) 0.037(7) Uiso 1 1 calc R . .
C11 C 1.1719(4) 0.1706(3) 0.2621(2) 0.0389(6) Uani 1 1 d . . .
H11A H 1.2227(10) 0.047(2) 0.2483(3) 0.036(7) Uiso 1 1 calc R . .
H11B H 1.2797(18) 0.1898(4) 0.2991(6) 0.046(7) Uiso 1 1 calc R . .
C12 C 0.9864(3) 0.1999(3) 0.3469(2) 0.0321(6) Uani 1 1 d . . .
H12A H 0.9423(8) 0.321(2) 0.3641(4) 0.040(7) Uiso 1 1 calc R . .
H12B H 1.0212(6) 0.1158(14) 0.4244(13) 0.040(7) Uiso 1 1 calc R . .
C13 C 0.6702(4) -0.1568(3) 0.1749(2) 0.0390(6) Uani 1 1 d . . .
H13A H 0.6082 -0.1211 0.0989 0.075(10) Uiso 1 1 calc R . .
H13B H 0.5772 -0.1825 0.2381 0.078(10) Uiso 1 1 calc R . .
H13C H 0.7874 -0.2600 0.1727 0.069(10) Uiso 1 1 calc R . .

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
N1 0.0231(10) 0.0315(11) 0.0260(10) -0.0055(8) 0.0000(8) -0.0106(8)
O1 0.0436(10) 0.0517(11) 0.0250(9) 0.0026(8) -0.0099(8) -0.0255(9)
C2 0.0247(12) 0.0258(12) 0.0298(13) -0.0054(10) 0.0026(10) -0.0083(9)
C3 0.0281(12) 0.0249(12) 0.0311(13) -0.0012(10) -0.0010(10) -0.0077(10)
C3A 0.0219(11) 0.0251(11) 0.0258(12) -0.0014(9) -0.0030(9) -0.0081(9)
C3B 0.0228(11) 0.0259(12) 0.0267(12) -0.0056(9) -0.0022(9) -0.0100(9)
C4 0.0338(13) 0.0301(13) 0.0255(12) 0.0006(10) -0.0022(10) -0.0128(10)
C5 0.0336(13) 0.0380(14) 0.0291(14) -0.0061(11) 0.0073(11) -0.0136(11)
C6 0.0256(13) 0.0296(13) 0.0404(15) -0.0094(11) 0.0059(11) -0.0054(10)
C7 0.0253(12) 0.0239(12) 0.0314(13) -0.0024(10) -0.0009(10) -0.0080(9)
O7 0.0319(10) 0.0328(10) 0.0373(11) 0.0039(8) 0.0018(8) 0.0015(7)
C7A 0.0262(12) 0.0254(11) 0.0240(12) -0.0034(9) 0.0022(10) -0.0121(9)
O8 0.0267(8) 0.0251(8) 0.0260(9) 0.0011(6) 0.0009(7) -0.0066(7)
C8A 0.0230(11) 0.0217(11) 0.0287(12) -0.0036(9) -0.0007(9) -0.0076(9)
C9 0.0263(12) 0.0361(13) 0.0315(13) -0.0048(11) 0.0051(10) -0.0140(10)
C10 0.0317(13) 0.0470(16) 0.0441(15) -0.0104(12) 0.0062(12) -0.0228(12)
C11 0.0228(12) 0.0458(16) 0.0500(17) -0.0114(13) -0.0052(11) -0.0115(11)
C12 0.0273(12) 0.0351(13) 0.0351(14) -0.0041(11) -0.0062(10) -0.0120(10)
C13 0.0442(16) 0.0381(15) 0.0402(16) -0.0097(12) 0.0020(13) -0.0207(13)

_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
N1 C2 1.298(3) . ?
N1 O1 1.300(2) . ?
N1 C8A 1.511(3) . ?
C2 C13 1.475(3) . ?
C2 C3 1.480(3) . ?
C3 C3A 1.537(3) . ?
C3A C3B 1.511(3) . ?
C3A C12 1.534(3) . ?
C3A C8A 1.550(3) . ?
C3B C7A 1.379(3) . ?
C3B C4 1.380(3) . ?
C4 C5 1.382(3) . ?
C5 C6 1.383(3) . ?
C6 C7 1.392(3) . ?
C7 O7 1.354(3) . ?
C7 C7A 1.389(3) . ?
C7A O8 1.385(3) . ?
O8 C8A 1.424(2) . ?
C8A C9 1.510(3) . ?
C9 C10 1.526(3) . ?
C10 C11 1.517(4) . ?
C11 C12 1.516(3) . ?

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
C2 N1 O1 127.23(19) . . ?
C2 N1 C8A 112.91(18) . . ?
O1 N1 C8A 119.74(17) . . ?
N1 C2 C13 122.3(2) . . ?
N1 C2 C3 111.25(19) . . ?
C13 C2 C3 126.4(2) . . ?
C2 C3 C3A 104.20(18) . . ?
C3B C3A C12 111.61(18) . . ?
C3B C3A C3 112.35(18) . . ?
C12 C3A C3 114.71(18) . . ?
C3B C3A C8A 99.55(17) . . ?
C12 C3A C8A 113.95(18) . . ?
C3 C3A C8A 103.44(17) . . ?
C7A C3B C4 120.8(2) . . ?
C7A C3B C3A 108.27(18) . . ?
C4 C3B C3A 131.0(2) . . ?
C3B C4 C5 118.0(2) . . ?
C4 C5 C6 120.9(2) . . ?
C5 C6 C7 121.9(2) . . ?
O7 C7 C7A 125.5(2) . . ?
O7 C7 C6 118.5(2) . . ?
C7A C7 C6 116.0(2) . . ?
C3B C7A O8 113.24(18) . . ?
C3B C7A C7 122.4(2) . . ?
O8 C7A C7 124.34(19) . . ?
C7A O8 C8A 105.62(16) . . ?
O8 C8A C9 111.20(18) . . ?
O8 C8A N1 108.46(16) . . ?
C9 C8A N1 109.01(17) . . ?
O8 C8A C3A 107.79(17) . . ?
C9 C8A C3A 118.26(18) . . ?
N1 C8A C3A 101.40(16) . . ?
C8A C9 C10 112.68(19) . . ?
C11 C10 C9 110.1(2) . . ?
C12 C11 C10 109.8(2) . . ?
C11 C12 C3A 112.91(19) . . ?

loop_
 _geom_hbond_atom_site_label_D
 _geom_hbond_atom_site_label_H
 _geom_hbond_atom_site_label_A
 _geom_hbond_distance_DH
 _geom_hbond_distance_HA
 _geom_hbond_distance_DA
 _geom_hbond_angle_DHA
 _geom_hbond_site_symmetry_A
O7 H7 O1  0.93(3) 1.74(3) 2.618(3) 157(3) 2_665

_diffrn_measured_fraction_theta_max    1.000
_diffrn_reflns_theta_full              24.97
_diffrn_measured_fraction_theta_full   1.000
_refine_diff_density_max    0.207
_refine_diff_density_min   -0.203
_refine_diff_density_rms    0.047