#------------------------------------------------------------------------------
#$Date: 2025-08-19 16:18:28 +0300 (Tue, 19 Aug 2025) $
#$Revision: 301805 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/22/62/2226207.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/. The original data for this entry
# were provided by IUCr Journals, http://journals.iucr.org/.
#
# The file may be used within the scientific community so long as
# proper attribution is given to the journal article from which the
# data were obtained.
#
data_2226207
loop_
_publ_author_name
'Kettmann, Viktor'
'Světlík, Jan'
'Veizerová, Lucia'
_publ_section_title
;
 rac-2-Methyl-3,4,5,6-tetrahydro-2H-2,6-methano-1,3-benzoxazocin-4-one
;
_journal_coeditor_code           KP2259
_journal_issue                   6
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o1402
_journal_paper_doi               10.1107/S1600536810017848
_journal_volume                  66
_journal_year                    2010
_chemical_formula_iupac          'C12 H13 N O2'
_chemical_formula_moiety         'C12 H13 N O2'
_chemical_formula_sum            'C12 H13 N O2'
_chemical_formula_weight         203.23
_chemical_melting_point          530
_chemical_name_systematic
;
rac-2-Methyl-3,4,5,6-tetrahydro-2H-2,6-methano-1,3-
benzoxazocin-4-one
;
_space_group_IT_number           2
_symmetry_cell_setting           triclinic
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_cell_angle_alpha                108.730(10)
_cell_angle_beta                 95.09(2)
_cell_angle_gamma                103.600(10)
_cell_formula_units_Z            2
_cell_length_a                   5.5640(10)
_cell_length_b                   9.820(2)
_cell_length_c                   10.596(2)
_cell_measurement_reflns_used    20
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      18
_cell_measurement_theta_min      7
_cell_volume                     524.37(18)
_computing_cell_refinement       'XSCANS (Siemens, 1991)'
_computing_data_collection       'XSCANS (Siemens, 1991)'
_computing_data_reduction        'XSCANS (Siemens, 1991)'
_computing_molecular_graphics    'PLATON (Spek, 2009)'
_computing_publication_material  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      296(2)
_diffrn_measured_fraction_theta_full 0.975
_diffrn_measured_fraction_theta_max 0.975
_diffrn_measurement_device_type  'Siemens P4 diffractometer'
_diffrn_measurement_method       ω/2θ
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0515
_diffrn_reflns_av_sigmaI/netI    0.0591
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -1
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            3821
_diffrn_reflns_theta_full        30.00
_diffrn_reflns_theta_max         30.00
_diffrn_reflns_theta_min         2.06
_diffrn_standards_decay_%        0
_diffrn_standards_interval_count 97
_diffrn_standards_number         3
_exptl_absorpt_coefficient_mu    0.088
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.287
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             216
_exptl_crystal_size_max          0.30
_exptl_crystal_size_mid          0.25
_exptl_crystal_size_min          0.20
_refine_diff_density_max         0.255
_refine_diff_density_min         -0.172
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.030
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     137
_refine_ls_number_reflns         2983
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.030
_refine_ls_R_factor_all          0.0683
_refine_ls_R_factor_gt           0.0489
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0608P)²+0.0887P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1318
_refine_ls_wR_factor_ref         0.1450
_reflns_number_gt                2242
_reflns_number_total             2983
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            kp2259.cif
_cod_data_source_block           I
_cod_original_cell_volume        524.37(17)
_cod_database_code               2226207
_cod_database_fobs_code          2226207
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'
loop_
_atom_site_type_symbol
_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
N N1 0.7300(2) 0.47999(13) 0.63412(11) 0.0368(3) Uani d . 1 . .
H H1 0.6390 0.5366 0.6239 0.044 Uiso calc R 1 . .
C C2 0.7192(3) 0.36033(16) 0.52401(13) 0.0390(3) Uani d . 1 . .
C C3 0.8893(3) 0.26336(19) 0.53502(14) 0.0464(3) Uani d . 1 . .
H H3A 1.0279 0.2843 0.4883 0.056 Uiso calc R 1 . .
H H3B 0.7957 0.1590 0.4900 0.056 Uiso calc R 1 . .
C C4 0.9955(3) 0.28856(17) 0.68250(14) 0.0431(3) Uani d . 1 . .
H H4 1.1317 0.2410 0.6836 0.052 Uiso calc R 1 . .
C C5 1.0990(2) 0.45662(18) 0.75980(15) 0.0432(3) Uani d . 1 . .
H H5A 1.1854 0.4750 0.8498 0.052 Uiso calc R 1 . .
H H5B 1.2176 0.5015 0.7127 0.052 Uiso calc R 1 . .
C C6 0.8791(2) 0.52435(15) 0.76906(12) 0.0353(3) Uani d . 1 . .
C C7 0.7943(3) 0.22442(16) 0.75190(13) 0.0391(3) Uani d . 1 . .
C C8 0.6692(2) 0.31756(14) 0.83327(12) 0.0345(3) Uani d . 1 . .
C C9 0.4875(3) 0.26224(16) 0.90078(14) 0.0405(3) Uani d . 1 . .
H H9 0.4077 0.3257 0.9555 0.049 Uiso calc R 1 . .
C C10 0.4269(3) 0.11180(18) 0.88560(16) 0.0506(4) Uani d . 1 . .
H H10 0.3057 0.0745 0.9303 0.061 Uiso calc R 1 . .
C C11 0.5454(4) 0.01657(18) 0.80448(17) 0.0570(4) Uani d . 1 . .
H H11 0.5035 -0.0843 0.7942 0.068 Uiso calc R 1 . .
C C12 0.7267(3) 0.07306(18) 0.73887(16) 0.0516(4) Uani d . 1 . .
H H12 0.8059 0.0088 0.6847 0.062 Uiso calc R 1 . .
C C13 0.9524(3) 0.69372(17) 0.83480(15) 0.0470(3) Uani d . 1 . .
H H13A 1.0388 0.7229 0.9260 0.071 Uiso calc R 1 . .
H H13B 0.8040 0.7276 0.8358 0.071 Uiso calc R 1 . .
H H13C 1.0608 0.7377 0.7842 0.071 Uiso calc R 1 . .
O O1 0.72022(17) 0.46921(10) 0.85435(9) 0.0372(2) Uani d . 1 . .
O O2 0.5800(2) 0.33318(13) 0.41568(10) 0.0537(3) Uani d . 1 . .
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 for Crystallography (1992).
Vol. C, Tables 4.2.6.8 and 6.1.1.4
;
H H 0.0000 0.0000
; International Tables for Crystallography (1992).
Vol. C, Tables 4.2.6.8 and 6.1.1.4
;
N N 0.0061 0.0033
; International Tables for Crystallography (1992).
Vol. C, Tables 4.2.6.8 and 6.1.1.4
;
O O 0.0106 0.0060
; International Tables for Crystallography (1992).
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 N1 C6 . . 127.38(11) ?
C2 N1 H1 . . 116.3 ?
C6 N1 H1 . . 116.3 ?
O2 C2 N1 . . 121.03(12) ?
O2 C2 C3 . . 120.90(12) ?
N1 C2 C3 . . 118.03(12) ?
C2 C3 C4 . . 113.10(11) ?
C2 C3 H3A . . 109.0 ?
C4 C3 H3A . . 109.0 ?
C2 C3 H3B . . 109.0 ?
C4 C3 H3B . . 109.0 ?
H3A C3 H3B . . 107.8 ?
C7 C4 C5 . . 108.71(11) ?
C7 C4 C3 . . 111.56(12) ?
C5 C4 C3 . . 108.61(12) ?
C7 C4 H4 . . 109.3 ?
C5 C4 H4 . . 109.3 ?
C3 C4 H4 . . 109.3 ?
C6 C5 C4 . . 107.95(11) ?
C6 C5 H5A . . 110.1 ?
C4 C5 H5A . . 110.1 ?
C6 C5 H5B . . 110.1 ?
C4 C5 H5B . . 110.1 ?
H5A C5 H5B . . 108.4 ?
O1 C6 N1 . . 108.80(10) ?
O1 C6 C13 . . 105.03(11) ?
N1 C6 C13 . . 109.14(11) ?
O1 C6 C5 . . 109.04(10) ?
N1 C6 C5 . . 109.98(11) ?
C13 C6 C5 . . 114.61(12) ?
C12 C7 C8 . . 117.50(14) ?
C12 C7 C4 . . 122.47(13) ?
C8 C7 C4 . . 120.03(12) ?
O1 C8 C9 . . 115.93(11) ?
O1 C8 C7 . . 122.84(12) ?
C9 C8 C7 . . 121.22(13) ?
C10 C9 C8 . . 119.44(14) ?
C10 C9 H9 . . 120.3 ?
C8 C9 H9 . . 120.3 ?
C11 C10 C9 . . 120.64(15) ?
C11 C10 H10 . . 119.7 ?
C9 C10 H10 . . 119.7 ?
C12 C11 C10 . . 119.36(15) ?
C12 C11 H11 . . 120.3 ?
C10 C11 H11 . . 120.3 ?
C11 C12 C7 . . 121.84(15) ?
C11 C12 H12 . . 119.1 ?
C7 C12 H12 . . 119.1 ?
C6 C13 H13A . . 109.5 ?
C6 C13 H13B . . 109.5 ?
H13A C13 H13B . . 109.5 ?
C6 C13 H13C . . 109.5 ?
H13A C13 H13C . . 109.5 ?
H13B C13 H13C . . 109.5 ?
C8 O1 C6 . . 116.70(10) ?
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
N1 C2 . 1.3489(17) ?
N1 C6 . 1.4634(16) ?
N1 H1 . 0.8600 ?
C2 O2 . 1.2399(16) ?
C2 C3 . 1.5137(19) ?
C3 C4 . 1.5399(19) ?
C3 H3A . 0.9700 ?
C3 H3B . 0.9700 ?
C4 C7 . 1.518(2) ?
C4 C5 . 1.526(2) ?
C4 H4 . 0.9800 ?
C5 C6 . 1.5203(18) ?
C5 H5A . 0.9700 ?
C5 H5B . 0.9700 ?
C6 O1 . 1.4568(16) ?
C6 C13 . 1.518(2) ?
C7 C12 . 1.402(2) ?
C7 C8 . 1.4011(18) ?
C8 O1 . 1.3873(16) ?
C8 C9 . 1.3959(19) ?
C9 C10 . 1.388(2) ?
C9 H9 . 0.9300 ?
C10 C11 . 1.386(2) ?
C10 H10 . 0.9300 ?
C11 C12 . 1.385(3) ?
C11 H11 . 0.9300 ?
C12 H12 . 0.9300 ?
C13 H13A . 0.9600 ?
C13 H13B . 0.9600 ?
C13 H13C . 0.9600 ?
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
N1 H1 O2 2_666 0.86 2.07 2.9274(15) 175.9
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
C6 N1 C2 O2 . . . . 178.31(13) ?
C6 N1 C2 C3 . . . . -3.9(2) ?
O2 C2 C3 C4 . . . . -165.37(14) ?
N1 C2 C3 C4 . . . . 16.9(2) ?
C2 C3 C4 C7 . . . . 71.70(16) ?
C2 C3 C4 C5 . . . . -48.10(17) ?
C7 C4 C5 C6 . . . . -54.82(14) ?
C3 C4 C5 C6 . . . . 66.74(14) ?
C2 N1 C6 O1 . . . . -97.04(15) ?
C2 N1 C6 C13 . . . . 148.87(14) ?
C2 N1 C6 C5 . . . . 22.34(18) ?
C4 C5 C6 O1 . . . . 66.77(13) ?
C4 C5 C6 N1 . . . . -52.46(14) ?
C4 C5 C6 C13 . . . . -175.85(11) ?
C5 C4 C7 C12 . . . . -156.59(12) ?
C3 C4 C7 C12 . . . . 83.67(16) ?
C5 C4 C7 C8 . . . . 23.03(16) ?
C3 C4 C7 C8 . . . . -96.72(15) ?
C12 C7 C8 O1 . . . . 179.75(11) ?
C4 C7 C8 O1 . . . . 0.11(18) ?
C12 C7 C8 C9 . . . . 1.13(19) ?
C4 C7 C8 C9 . . . . -178.51(11) ?
O1 C8 C9 C10 . . . . -179.60(11) ?
C7 C8 C9 C10 . . . . -0.89(19) ?
C8 C9 C10 C11 . . . . 0.1(2) ?
C9 C10 C11 C12 . . . . 0.4(2) ?
C10 C11 C12 C7 . . . . -0.1(2) ?
C8 C7 C12 C11 . . . . -0.6(2) ?
C4 C7 C12 C11 . . . . 178.99(13) ?
C9 C8 O1 C6 . . . . -170.69(10) ?
C7 C8 O1 C6 . . . . 10.63(16) ?
N1 C6 O1 C8 . . . . 76.17(13) ?
C13 C6 O1 C8 . . . . -167.08(10) ?
C5 C6 O1 C8 . . . . -43.79(14) ?
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 PubChem 118989494
