data_2203198
loop_
_publ_author_name
'Argay, Gyula'
'F\'abi\'an, L\'aszl\'o'
'K\'alm\'an, Alajos'
'Bern\'ath, G\'abor'
'Cs. Gyarmati, Zsuzsanna'
_publ_section_title
;
cis-7-Azabicyclo[4.2.0]octan-8-one
;
_journal_issue                 2
_journal_name_full             'Acta Crystallographica, Section E'
_journal_page_first            o170
_journal_page_last             o172
_journal_volume                60
_journal_year                  2004
_chemical_formula_iupac        'C7 H11 N O'
_chemical_formula_moiety       'C7 H11 N O'
_chemical_formula_sum          'C7 H11 N O'
_chemical_formula_weight       125.17
_chemical_melting_point        329-330
_chemical_name_common          ?
_chemical_name_systematic
;
 cis-7-azabicyclo[4.2.0]octan-8-one
;
_symmetry_cell_setting         monoclinic
_symmetry_space_group_name_Hall '-P 2ybc'
_symmetry_space_group_name_H-M 'P 21/c'
_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               112.000(10)
_cell_angle_gamma              90.00
_cell_formula_units_Z          4
_cell_length_a                 11.3330(10)
_cell_length_b                 6.4740(10)
_cell_length_c                 10.1810(10)
_cell_measurement_reflns_used  25
_cell_measurement_temperature  293(2)
_cell_measurement_theta_max    32.34
_cell_measurement_theta_min    29.31
_cell_volume                   692.59(14)
_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, 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 0.992
_diffrn_measured_fraction_theta_max 0.992
_diffrn_measurement_device_type 'Enraf-Nonius CAD-4'
_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 0.0103
_diffrn_reflns_av_sigmaI/netI  0.0089
_diffrn_reflns_limit_h_max     7
_diffrn_reflns_limit_h_min     -14
_diffrn_reflns_limit_k_max     8
_diffrn_reflns_limit_k_min     -1
_diffrn_reflns_limit_l_max     12
_diffrn_reflns_limit_l_min     -12
_diffrn_reflns_number          1554
_diffrn_reflns_theta_full      75.55
_diffrn_reflns_theta_max       75.55
_diffrn_reflns_theta_min       4.21
_diffrn_standards_decay_%      8
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time 60
_diffrn_standards_number       3
_exptl_absorpt_coefficient_mu  0.643
_exptl_absorpt_correction_T_max 0.8218
_exptl_absorpt_correction_T_min 0.7657
_exptl_absorpt_correction_type psi-scan
_exptl_absorpt_process_details '(North et al., 1968)'
_exptl_crystal_colour          colourless
_exptl_crystal_density_diffrn  1.200
_exptl_crystal_density_meas    ?
_exptl_crystal_density_method  'not measured'
_exptl_crystal_description     prism
_exptl_crystal_F_000           272
_exptl_crystal_size_max        0.50
_exptl_crystal_size_mid        0.35
_exptl_crystal_size_min        0.30
_refine_diff_density_max       0.228
_refine_diff_density_min       -0.146
_refine_ls_extinction_coef     0.012(3)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_extinction_method   SHELXL97
_refine_ls_goodness_of_fit_ref 1.304
_refine_ls_hydrogen_treatment  riding
_refine_ls_matrix_type         full
_refine_ls_number_parameters   108
_refine_ls_number_reflns       1433
_refine_ls_number_restraints   188
_refine_ls_restrained_S_all    1.236
_refine_ls_R_factor_all        0.0560
_refine_ls_R_factor_gt         0.0521
_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^)+(0.101P)^2^+0.05P] where P = (Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme    calc
_refine_ls_wR_factor_gt        0.1824
_refine_ls_wR_factor_ref       0.1853
_reflns_number_gt              1256
_reflns_number_total           1433
_reflns_threshold_expression   I>2\s(I)
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'x, -y+1/2, z+1/2'
'-x, -y, -z'
'-x, y-1/2, -z-1/2'
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 0.29462(14) 0.4259(2) 0.41635(14) 0.0589(4) Uani d DU 1 . . C
H1A 0.3219 0.5110 0.3532 0.077 Uiso calc PR 0.769(7) A 1 H
H1B 0.3234 0.5103 0.3542 0.077 Uiso calc PR 0.231(7) A 2 H
C2A 0.1508(3) 0.4204(8) 0.3717(6) 0.0667(10) Uani d PDU 0.769(7) A 1 C
H2A1 0.1201 0.5590 0.3764 0.087 Uiso calc PR 0.769(7) A 1 H
H2A2 0.1128 0.3738 0.2743 0.087 Uiso calc PR 0.769(7) A 1 H
C3A 0.1094(3) 0.2785(4) 0.4650(4) 0.0745(7) Uani d PDU 0.769(7) A 1 C
H3A1 0.0175 0.2661 0.4250 0.097 Uiso calc PR 0.769(7) A 1 H
H3A2 0.1331 0.3406 0.5580 0.097 Uiso calc PR 0.769(7) A 1 H
C4A 0.1676(3) 0.0642(5) 0.4810(4) 0.0745(7) Uani d PDU 0.769(7) A 1 C
H4A1 0.0988 -0.0342 0.4407 0.097 Uiso calc PR 0.769(7) A 1 H
H4A2 0.2072 0.0342 0.5814 0.097 Uiso calc PR 0.769(7) A 1 H
C5A 0.2654(4) 0.0250(7) 0.4148(6) 0.0622(8) Uani d PDU 0.769(7) A 1 C
H5A1 0.3134 -0.0988 0.4555 0.081 Uiso calc PR 0.769(7) A 1 H
H5A2 0.2224 0.0032 0.3138 0.081 Uiso calc PR 0.769(7) A 1 H
C2B 0.1574(9) 0.470(2) 0.394(3) 0.072(4) Uani d PDU 0.231(7) A 2 C
H2B1 0.1540 0.5391 0.4774 0.094 Uiso calc PR 0.231(7) A 2 H
H2B2 0.1207 0.5616 0.3139 0.094 Uiso calc PR 0.231(7) A 2 H
C3B 0.0810(9) 0.2735(17) 0.3687(19) 0.103(3) Uani d PDU 0.231(7) A 2 C
H3B1 0.0691 0.2220 0.2751 0.134 Uiso calc PR 0.231(7) A 2 H
H3B2 -0.0025 0.3051 0.3693 0.134 Uiso calc PR 0.231(7) A 2 H
C4B 0.1404(11) 0.104(3) 0.476(2) 0.103(3) Uani d PDU 0.231(7) A 2 C
H4B1 0.0841 -0.0137 0.4612 0.134 Uiso calc PR 0.231(7) A 2 H
H4B2 0.1641 0.1539 0.5723 0.134 Uiso calc PR 0.231(7) A 2 H
C5B 0.2567(16) 0.053(2) 0.442(2) 0.084(5) Uani d PDU 0.231(7) A 2 C
H5B1 0.3020 -0.0546 0.5073 0.109 Uiso calc PR 0.231(7) A 2 H
H5B2 0.2246 -0.0097 0.3482 0.109 Uiso calc PR 0.231(7) A 2 H
C6 0.35598(15) 0.2074(3) 0.44054(16) 0.0610(5) Uani d DU 1 A . C
H6A 0.4135 0.1907 0.3895 0.079 Uiso calc PR 0.769(7) A 1 H
H6B 0.4071 0.1713 0.3847 0.079 Uiso calc PR 0.231(7) A 2 H
N7 0.42568(13) 0.2716(2) 0.58807(14) 0.0661(4) Uani d U 1 . . N
H7 0.4799 0.2087 0.6598 0.086 Uiso calc R 1 A . H
C8 0.37583(14) 0.4609(2) 0.57222(15) 0.0589(4) Uani d U 1 A . C
O1 0.38991(13) 0.60397(19) 0.65522(12) 0.0788(5) 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 0.0662(9) 0.0549(8) 0.0517(8) -0.0100(6) 0.0175(6) 0.0072(6)
C2A 0.0619(16) 0.059(2) 0.0662(19) 0.0025(11) 0.0095(12) -0.0031(18)
C3A 0.0711(12) 0.0739(13) 0.0868(14) -0.0113(8) 0.0392(11) -0.0019(9)
C4A 0.0711(12) 0.0739(13) 0.0868(14) -0.0113(8) 0.0392(11) -0.0019(9)
C5A 0.0791(16) 0.0479(17) 0.065(2) -0.0039(12) 0.0328(12) -0.0103(14)
C2B 0.067(5) 0.049(6) 0.082(9) -0.009(4) 0.007(4) -0.009(5)
C3B 0.064(4) 0.094(6) 0.149(8) -0.009(3) 0.038(4) 0.019(5)
C4B 0.064(4) 0.094(6) 0.149(8) -0.009(3) 0.038(4) 0.019(5)
C5B 0.140(11) 0.044(5) 0.074(8) 0.008(5) 0.047(6) -0.022(4)
C6 0.0633(9) 0.0638(9) 0.0589(8) -0.0011(6) 0.0263(7) -0.0006(6)
N7 0.0622(8) 0.0669(8) 0.0588(8) 0.0041(6) 0.0107(6) 0.0050(6)
C8 0.0591(8) 0.0573(8) 0.0544(8) -0.0117(6) 0.0144(6) 0.0031(6)
O1 0.0929(9) 0.0622(8) 0.0672(7) -0.0139(6) 0.0137(6) -0.0088(5)
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 0.0091 '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 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 '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
C2B C1 C8 . . 108.2(9) ?
C2A C1 C8 . . 118.5(2) ?
C2B C1 C6 . . 124.7(5) ?
C2A C1 C6 . . 113.1(2) ?
C8 C1 C6 . . 84.87(11) ?
C2A C1 H1A . . 112.5 ?
C8 C1 H1A . . 112.5 ?
C6 C1 H1A . . 112.5 ?
C2B C1 H1B . . 111.8 ?
C8 C1 H1B . . 111.8 ?
C6 C1 H1B . . 111.8 ?
C3A C2A C1 . . 112.1(3) ?
C3A C2A H2A1 . . 109.2 ?
C1 C2A H2A1 . . 109.2 ?
C3A C2A H2A2 . . 109.2 ?
C1 C2A H2A2 . . 109.2 ?
H2A1 C2A H2A2 . . 107.9 ?
C2A C3A C4A . . 113.4(3) ?
C2A C3A H3A1 . . 108.9 ?
C4A C3A H3A1 . . 108.9 ?
C2A C3A H3A2 . . 108.9 ?
C4A C3A H3A2 . . 108.9 ?
H3A1 C3A H3A2 . . 107.7 ?
C3A C4A C5A . . 117.7(3) ?
C3A C4A H4A1 . . 107.9 ?
C5A C4A H4A1 . . 107.9 ?
C3A C4A H4A2 . . 107.9 ?
C5A C4A H4A2 . . 107.9 ?
H4A1 C4A H4A2 . . 107.2 ?
C6 C5A C4A . . 110.6(3) ?
C6 C5A H5A1 . . 109.5 ?
C4A C5A H5A1 . . 109.5 ?
C6 C5A H5A2 . . 109.5 ?
C4A C5A H5A2 . . 109.5 ?
H5A1 C5A H5A2 . . 108.1 ?
C3B C2B C1 . . 111.0(8) ?
C3B C2B H2B1 . . 109.4 ?
C1 C2B H2B1 . . 109.4 ?
C3B C2B H2B2 . . 109.4 ?
C1 C2B H2B2 . . 109.4 ?
H2B1 C2B H2B2 . . 108.0 ?
C2B C3B C4B . . 114.5(15) ?
C2B C3B H3B1 . . 108.6 ?
C4B C3B H3B1 . . 108.6 ?
C2B C3B H3B2 . . 108.6 ?
C4B C3B H3B2 . . 108.6 ?
H3B1 C3B H3B2 . . 107.6 ?
C3B C4B C5B . . 100.5(14) ?
C3B C4B H4B1 . . 111.7 ?
C5B C4B H4B1 . . 111.7 ?
C3B C4B H4B2 . . 111.7 ?
C5B C4B H4B2 . . 111.7 ?
H4B1 C4B H4B2 . . 109.4 ?
C6 C5B C4B . . 124.8(11) ?
C6 C5B H5B1 . . 106.1 ?
C4B C5B H5B1 . . 106.1 ?
C6 C5B H5B2 . . 106.1 ?
C4B C5B H5B2 . . 106.1 ?
H5B1 C5B H5B2 . . 106.3 ?
N7 C6 C5B . . 107.3(8) ?
N7 C6 C5A . . 117.7(2) ?
N7 C6 C1 . . 86.67(11) ?
C5B C6 C1 . . 108.2(7) ?
C5A C6 C1 . . 116.5(2) ?
N7 C6 H6A . . 111.3 ?
C5A C6 H6A . . 111.3 ?
C1 C6 H6A . . 111.3 ?
N7 C6 H6B . . 116.8 ?
C5B C6 H6B . . 116.8 ?
C1 C6 H6B . . 116.8 ?
C8 N7 C6 . . 95.45(12) ?
C8 N7 H7 . . 132.3 ?
C6 N7 H7 . . 132.3 ?
O1 C8 N7 . . 132.26(14) ?
O1 C8 C1 . . 134.71(15) ?
N7 C8 C1 . . 93.01(12) ?
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 C2B . 1.513(8) ?
C1 C2A . 1.519(4) yes
C1 C8 . 1.524(2) yes
C1 C6 . 1.555(2) yes
C1 H1A . 0.9800 ?
C1 H1B . 0.9800 ?
C2A C3A . 1.516(5) yes
C2A H2A1 . 0.9700 ?
C2A H2A2 . 0.9700 ?
C3A C4A . 1.519(4) yes
C3A H3A1 . 0.9700 ?
C3A H3A2 . 0.9700 ?
C4A C5A . 1.519(4) yes
C4A H4A1 . 0.9700 ?
C4A H4A2 . 0.9700 ?
C5A C6 . 1.521(4) yes
C5A H5A1 . 0.9700 ?
C5A H5A2 . 0.9700 ?
C2B C3B . 1.506(8) ?
C2B H2B1 . 0.9700 ?
C2B H2B2 . 0.9700 ?
C3B C4B . 1.514(8) ?
C3B H3B1 . 0.9700 ?
C3B H3B2 . 0.9700 ?
C4B C5B . 1.521(8) ?
C4B H4B1 . 0.9700 ?
C4B H4B2 . 0.9700 ?
C5B C6 . 1.507(12) ?
C5B H5B1 . 0.9700 ?
C5B H5B2 . 0.9700 ?
C6 N7 . 1.4710(19) yes
C6 H6A . 0.9800 ?
C6 H6B . 0.9800 ?
N7 C8 . 1.334(2) yes
N7 H7 . 0.8600 ?
C8 O1 . 1.2232(19) 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
N7 H7 O1 4_657 0.86 2.03 2.8781(17) 171
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
C8 C1 C2A C3A . . . . -49.1(4) ?
C6 C1 C2A C3A . . . . 47.8(4) ?
C1 C2A C3A C4A . . . . -51.1(5) ?
C2A C3A C4A C5A . . . . 5.1(5) ?
C3A C4A C5A C6 . . . . 41.9(5) ?
C8 C1 C2B C3B . . . . -108.3(16) ?
C6 C1 C2B C3B . . . . -12(2) ?
C1 C2B C3B C4B . . . . 50(2) ?
C2B C3B C4B C5B . . . . -67(2) ?
C3B C4B C5B C6 . . . . 56(2) ?
C4B C5B C6 N7 . . . . 69(2) ?
C4B C5B C6 C1 . . . . -24(2) ?
C4A C5A C6 N7 . . . . 56.2(5) ?
C4A C5A C6 C1 . . . . -44.6(5) ?
C2B C1 C6 N7 . . . . -108.4(11) ?
C2A C1 C6 N7 . . . . -118.6(3) ?
C8 C1 C6 N7 . . . . 0.16(10) ?
C2B C1 C6 C5B . . . . -1.3(14) ?
C8 C1 C6 C5B . . . . 107.3(9) ?
C2A C1 C6 C5A . . . . 0.8(3) ?
C8 C1 C6 C5A . . . . 119.6(2) ?
C5B C6 N7 C8 . . . . -108.3(7) ?
C5A C6 N7 C8 . . . . -118.5(2) ?
C1 C6 N7 C8 . . . . -0.18(12) ?
C6 N7 C8 O1 . . . . 178.67(17) ?
C6 N7 C8 C1 . . . . 0.19(12) ?
C2B C1 C8 O1 . . . . -53.7(7) ?
C2A C1 C8 O1 . . . . -65.1(3) ?
C6 C1 C8 O1 . . . . -178.60(18) ?
C2B C1 C8 N7 . . . . 124.7(6) ?
C2A C1 C8 N7 . . . . 113.3(3) ?
C6 C1 C8 N7 . . . . -0.18(12) ?