data_2203199
loop_
_publ_author_name
'Argay, Gyula'
'K\'alm\'an, Alajos'
'Bern\'ath, G\'abor'
'Cs. Gyarmati, Zsuzsanna'
_publ_section_title
;
 cis-8-Azabicyclo[5.2.0]nonan-9-one
;
_journal_issue                 2
_journal_name_full             'Acta Crystallographica, Section E'
_journal_page_first            o173
_journal_page_last             o175
_journal_volume                60
_journal_year                  2004
_chemical_formula_moiety       'C8 H13 N O'
_chemical_formula_sum          'C8 H13 N O'
_chemical_formula_weight       139.19
_chemical_melting_point        328-329
_chemical_name_common          ?
_chemical_name_systematic
;
 cis-8-azabicyclo[5.2.0]nonan-9-one
;
_symmetry_cell_setting         orthorhombic
_symmetry_space_group_name_Hall 'P 2ac 2ab'
_symmetry_space_group_name_H-M 'P 21 21 21'
_atom_sites_solution_hydrogens geom
_atom_sites_solution_primary   direct
_atom_sites_solution_secondary difmap
_audit_creation_method         SHELXL-97
_cell_angle_alpha              90.00
_cell_angle_beta               90.00
_cell_angle_gamma              90.00
_cell_formula_units_Z          4
_cell_length_a                 6.6830(10)
_cell_length_b                 9.1660(10)
_cell_length_c                 12.696(2)
_cell_measurement_reflns_used  25
_cell_measurement_temperature  293(2)
_cell_measurement_theta_max    25.54
_cell_measurement_theta_min    24.34
_cell_volume                   777.71(19)
_computing_cell_refinement     'CAD-4 EXPRESS'
_computing_data_collection     'CAD-4 EXPRESS (Enraf-Nonius, 1992)'
_computing_data_reduction      'XCAD4 (Harms 1996)'
_computing_molecular_graphics
'ORTEP-3 (Farrugia, 1997) and RPluto in CSD (Allen, F. H. (2002)'
_computing_publication_material SHELXL97
_computing_structure_refinement 'SHELXL97 (Sheldrick, 1997)'
_computing_structure_solution  'SHELXS97 (Sheldrick, 1997)'
_diffrn_ambient_temperature    293(2)
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.985
_diffrn_measured_fraction_theta_max 0.985
_diffrn_measurement_device_type 'Enraf-Nonius CAD4'
_diffrn_measurement_method     \w-\q
_diffrn_radiation_monochromator graphite
_diffrn_radiation_source       'fine-focus sealed tube'
_diffrn_radiation_type         'CU k\a'
_diffrn_radiation_wavelength   1.54180
_diffrn_reflns_av_R_equivalents 0.0173
_diffrn_reflns_av_sigmaI/netI  0.0192
_diffrn_reflns_limit_h_max     8
_diffrn_reflns_limit_h_min     -8
_diffrn_reflns_limit_k_max     11
_diffrn_reflns_limit_k_min     -11
_diffrn_reflns_limit_l_max     15
_diffrn_reflns_limit_l_min     -15
_diffrn_reflns_number          1863
_diffrn_reflns_theta_full      74.85
_diffrn_reflns_theta_max       74.85
_diffrn_reflns_theta_min       5.95
_diffrn_standards_decay_%      16
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time 60
_diffrn_standards_number       3
_exptl_absorpt_coefficient_mu  0.620
_exptl_absorpt_correction_T_max 0.9099
_exptl_absorpt_correction_T_min 0.8920
_exptl_absorpt_correction_type psi-scan
_exptl_absorpt_process_details '(North et al., 1968)'
_exptl_crystal_colour          colourless
_exptl_crystal_density_diffrn  1.189
_exptl_crystal_density_meas    ?
_exptl_crystal_density_method  'not measured'
_exptl_crystal_description     prism
_exptl_crystal_F_000           304
_exptl_crystal_size_max        0.35
_exptl_crystal_size_mid        0.20
_exptl_crystal_size_min        0.15
_refine_diff_density_max       0.225
_refine_diff_density_min       -0.275
_refine_ls_abs_structure_details ?
_refine_ls_abs_structure_Flack ?
_refine_ls_extinction_coef     ?
_refine_ls_extinction_method   none
_refine_ls_goodness_of_fit_ref 1.979
_refine_ls_hydrogen_treatment  constr
_refine_ls_matrix_type         full
_refine_ls_number_parameters   91
_refine_ls_number_reflns       941
_refine_ls_number_restraints   86
_refine_ls_restrained_S_all    1.889
_refine_ls_R_factor_all        0.0714
_refine_ls_R_factor_gt         0.0660
_refine_ls_shift/su_max        0.000
_refine_ls_shift/su_mean       0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w = 1/[\s^2^(Fo^2^)+(0.1000P)^2^] where P = (Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme    calc
_refine_ls_wR_factor_gt        0.2144
_refine_ls_wR_factor_ref       0.2270
_reflns_number_gt              842
_reflns_number_total           941
_reflns_threshold_expression   I>2\s(I)
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'-x, y+1/2, -z+1/2'
'x+1/2, -y+1/2, -z'
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
C1 0.4015(4) 0.4291(4) 0.2136(2) 0.0546(7) Uani d U 1 . . C
H1 0.3830 0.5342 0.2033 0.071 Uiso calc R 1 . . H
C2 0.4753(4) 0.3970(4) 0.3239(2) 0.0539(7) Uani d U 1 . . C
H2A 0.5070 0.2940 0.3290 0.070 Uiso calc R 1 . . H
H2B 0.5976 0.4513 0.3361 0.070 Uiso calc R 1 . . H
C3 0.3248(5) 0.4357(4) 0.4092(2) 0.0624(9) Uani d U 1 . . C
H3A 0.3963 0.4493 0.4750 0.081 Uiso calc R 1 . . H
H3B 0.2630 0.5282 0.3912 0.081 Uiso calc R 1 . . H
C4 0.1599(6) 0.3236(5) 0.4268(3) 0.0734(10) Uani d U 1 . . C
H4A 0.0787 0.3558 0.4857 0.095 Uiso calc R 1 . . H
H4B 0.2221 0.2322 0.4471 0.095 Uiso calc R 1 . . H
C5 0.0210(5) 0.2938(5) 0.3335(3) 0.0715(10) Uani d U 1 . . C
H5A -0.0425 0.3847 0.3130 0.093 Uiso calc R 1 . . H
H5B -0.0837 0.2275 0.3561 0.093 Uiso calc R 1 . . H
C6 0.1239(5) 0.2294(4) 0.2382(3) 0.0657(9) Uani d U 1 . . C
H6A 0.2252 0.1609 0.2617 0.085 Uiso calc R 1 . . H
H6B 0.0265 0.1755 0.1970 0.085 Uiso calc R 1 . . H
C7 0.2206(5) 0.3426(4) 0.1692(2) 0.0609(8) Uani d U 1 . . C
H7 0.1206 0.4083 0.1386 0.079 Uiso calc R 1 . . H
N8 0.3600(5) 0.2879(4) 0.0878(2) 0.0723(9) Uani d U 1 . . N
H8 0.3438 0.2285 0.0361 0.094 Uiso calc R 1 . . H
C9 0.5201(5) 0.3623(4) 0.1218(2) 0.0630(8) Uani d U 1 . . C
O1 0.6909(4) 0.3724(4) 0.0909(2) 0.0895(10) Uani d U 1 . . O
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
C1 0.0524(15) 0.0613(15) 0.0499(14) 0.0004(13) 0.0036(11) -0.0037(11)
C2 0.0428(13) 0.0676(16) 0.0511(14) 0.0004(12) -0.0005(11) -0.0063(12)
C3 0.0613(19) 0.0773(19) 0.0488(13) 0.0043(15) 0.0045(14) -0.0116(14)
C4 0.0635(19) 0.097(2) 0.0593(17) -0.0014(19) 0.0131(14) 0.0051(16)
C5 0.0472(15) 0.087(2) 0.080(2) -0.0049(16) 0.0019(15) 0.0166(18)
C6 0.0565(15) 0.0700(17) 0.0705(18) -0.0115(15) -0.0135(14) 0.0045(15)
C7 0.0574(16) 0.0743(18) 0.0511(14) 0.0031(15) -0.0125(12) 0.0026(14)
N8 0.0811(18) 0.0895(19) 0.0464(12) 0.0014(16) -0.0085(13) -0.0136(13)
C9 0.0664(17) 0.0780(18) 0.0447(13) 0.0035(16) 0.0049(12) -0.0052(13)
O1 0.0736(17) 0.125(2) 0.0703(15) -0.0044(17) 0.0238(14) -0.0227(16)
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0000 '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 0.0311 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0000 '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_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle
_geom_angle_publ_flag
C2 C1 C7 . . 119.4(3) ?
C2 C1 C9 . . 117.1(2) ?
C7 C1 C9 . . 85.6(2) ?
C2 C1 H1 . . 110.8 ?
C7 C1 H1 . . 110.8 ?
C9 C1 H1 . . 110.8 ?
C3 C2 C1 . . 113.5(2) ?
C3 C2 H2A . . 108.9 ?
C1 C2 H2A . . 108.9 ?
C3 C2 H2B . . 108.9 ?
C1 C2 H2B . . 108.9 ?
H2A C2 H2B . . 107.7 ?
C4 C3 C2 . . 115.2(3) ?
C4 C3 H3A . . 108.5 ?
C2 C3 H3A . . 108.5 ?
C4 C3 H3B . . 108.5 ?
C2 C3 H3B . . 108.5 ?
H3A C3 H3B . . 107.5 ?
C3 C4 C5 . . 116.4(3) ?
C3 C4 H4A . . 108.2 ?
C5 C4 H4A . . 108.2 ?
C3 C4 H4B . . 108.2 ?
C5 C4 H4B . . 108.2 ?
H4A C4 H4B . . 107.3 ?
C4 C5 C6 . . 114.4(3) ?
C4 C5 H5A . . 108.7 ?
C6 C5 H5A . . 108.7 ?
C4 C5 H5B . . 108.7 ?
C6 C5 H5B . . 108.7 ?
H5A C5 H5B . . 107.6 ?
C7 C6 C5 . . 113.1(3) ?
C7 C6 H6A . . 109.0 ?
C5 C6 H6A . . 109.0 ?
C7 C6 H6B . . 109.0 ?
C5 C6 H6B . . 109.0 ?
H6A C6 H6B . . 107.8 ?
N8 C7 C6 . . 116.4(3) ?
N8 C7 C1 . . 86.3(2) ?
C6 C7 C1 . . 118.4(2) ?
N8 C7 H7 . . 111.2 ?
C6 C7 H7 . . 111.2 ?
C1 C7 H7 . . 111.2 ?
C9 N8 C7 . . 96.1(2) ?
C9 N8 H8 . . 132.0 ?
C7 N8 H8 . . 132.0 ?
O1 C9 N8 . . 133.4(3) ?
O1 C9 C1 . . 134.6(3) ?
N8 C9 C1 . . 92.0(2) ?
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
C1 C2 . 1.513(4) yes
C1 C7 . 1.552(4) yes
C1 C9 . 1.537(4) yes
C1 H1 . 0.9800 ?
C2 C3 . 1.521(4) yes
C2 H2A . 0.9700 ?
C2 H2B . 0.9700 ?
C3 C4 . 1.524(5) yes
C3 H3A . 0.9700 ?
C3 H3B . 0.9700 ?
C4 C5 . 1.530(5) yes
C4 H4A . 0.9700 ?
C4 H4B . 0.9700 ?
C5 C6 . 1.511(5) yes
C5 H5A . 0.9700 ?
C5 H5B . 0.9700 ?
C6 C7 . 1.505(5) yes
C6 H6A . 0.9700 ?
C6 H6B . 0.9700 ?
C7 N8 . 1.478(4) yes
C7 H7 . 0.9800 ?
N8 C9 . 1.340(5) yes
N8 H8 . 0.8600 ?
C9 O1 . 1.210(4) yes
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_site_symmetry_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
N8 H8 O1 4_455 0.86 2.12 2.929(4) 156.5
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
C7 C1 C2 C3 . . . . -65.4(4) ?
C9 C1 C2 C3 . . . . -166.3(3) ?
C1 C2 C3 C4 . . . . 80.4(4) ?
C2 C3 C4 C5 . . . . -61.9(4) ?
C3 C4 C5 C6 . . . . 63.3(4) ?
C4 C5 C6 C7 . . . . -83.5(4) ?
C5 C6 C7 N8 . . . . 167.3(3) ?
C5 C6 C7 C1 . . . . 66.5(4) ?
C2 C1 C7 N8 . . . . -117.9(3) ?
C9 C1 C7 N8 . . . . 0.9(2) ?
C2 C1 C7 C6 . . . . 0.3(4) ?
C9 C1 C7 C6 . . . . 119.0(3) ?
C6 C7 N8 C9 . . . . -121.0(3) ?
C1 C7 N8 C9 . . . . -1.0(3) ?
C7 N8 C9 O1 . . . . -178.6(5) ?
C7 N8 C9 C1 . . . . 1.0(3) ?
C2 C1 C9 O1 . . . . -60.5(6) ?
C7 C1 C9 O1 . . . . 178.7(5) ?
C2 C1 C9 N8 . . . . 119.9(3) ?
C7 C1 C9 N8 . . . . -1.0(3) ?