Conformation of Eight-Membered Benzoannulated Lactams by Combined NMR and DFT Studies
Agnieszka Witosińska; Bogdan Musielak; Paweł Serda; Maria Owińska; Barbara Rys; Journal of Organic Chemistry 77 (2012) 9784–9794; doi:10.1021/jo301859h

data_4027677
_publ_contact_author_address
;
Faculty of Chemistry
Jagiellonian University
Ingardena 3
30-060 Krak\'ow, Poland
;
_publ_contact_author_email       rys@chemia.uj.edu.pl
_publ_contact_author_name        'Rys, B.'
_publ_section_title
;
 Conformation of Eight-Membered Benzoannulated Lactams by Combined NMR and
 DFT Studies
;
_journal_name_full               'Journal of Organic Chemistry'
_journal_page_first              9784
_journal_page_last               9794
_journal_paper_doi               10.1021/jo301859h
_journal_volume                  77
_journal_year                    2012
_chemical_compound_source        'synthesis as described'
_chemical_formula_moiety         'C11 H13 N O'
_chemical_formula_sum            'C11 H13 N O'
_chemical_formula_weight         175.22
_chemical_name_common            arx
_chemical_name_systematic
;
3,4,5,6-tetrahydro-1H-benzo[b]azocin-2-one
;
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_Int_Tables_number      14
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 1 21/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_conform_dict_location     ftp://ftp.iucr.org/pub/cif_core.dic
_audit_conform_dict_name         cif_core.dic
_audit_conform_dict_version      2.3
_audit_creation_date             2012-08-16T17:30:44-00:00
_audit_creation_method           'WinGX routine CIF_UPDATE'
_cell_angle_alpha                90
_cell_angle_beta                 111.4150(10)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   13.1243(4)
_cell_length_b                   4.76300(10)
_cell_length_c                   15.8937(6)
_cell_measurement_reflns_used    3208
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      25.028
_cell_measurement_theta_min      2.91
_cell_measurement_wavelength     0.71073
_cell_volume                     924.94(5)
_computing_cell_refinement       'HKL Scalepack (Otwinowski & Minor 1997)'
_computing_data_collection       'Collect (Nonius BV, 1997-2000)'
_computing_data_reduction
'HKL Denzo and Scalepack (Otwinowski & Minor 1997)'
_computing_molecular_graphics    'Ortep-3 for Windows (Farrugia, 1997)'
_computing_publication_material  'WinGX publication routines (Farrugia, 1999)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-86 (Sheldrick, 1986)'
_diffrn_ambient_temperature      293(2)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 9
_diffrn_measured_fraction_theta_full 0.995
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measurement_device       '95mm CCD camera on \k-goniostat'
_diffrn_measurement_device_type  KappaCCD
_diffrn_measurement_method       'CCD rotation images, thick slices'
_diffrn_orient_matrix_type       'by Nonius Collect from scalepack cell'
_diffrn_orient_matrix_UB_11      0.24902E-1
_diffrn_orient_matrix_UB_12      0.481632E-1
_diffrn_orient_matrix_UB_13      0.61309E-1
_diffrn_orient_matrix_UB_21      -0.199295
_diffrn_orient_matrix_UB_22      0.533498E-1
_diffrn_orient_matrix_UB_23      0.389242E-1
_diffrn_orient_matrix_UB_31      0.23853E-2
_diffrn_orient_matrix_UB_32      -0.33764E-1
_diffrn_orient_matrix_UB_33      0.584968E-1
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0476
_diffrn_reflns_av_unetI/netI     0.0381
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_k_max       5
_diffrn_reflns_limit_k_min       -5
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            5843
_diffrn_reflns_theta_full        25.02
_diffrn_reflns_theta_max         25.02
_diffrn_reflns_theta_min         3.33
_diffrn_source                   'Enraf Nonius FR590'
_exptl_absorpt_coefficient_mu    0.081
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.258
_exptl_crystal_description       needles
_exptl_crystal_F_000             376
_exptl_crystal_size_max          0.4
_exptl_crystal_size_mid          0.18
_exptl_crystal_size_min          0.1
_refine_diff_density_max         0.126
_refine_diff_density_min         -0.171
_refine_diff_density_rms         0.033
_refine_ls_extinction_coef       0.048(9)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_ref   1.049
_refine_ls_hydrogen_treatment    refall
_refine_ls_matrix_type           full
_refine_ls_number_parameters     171
_refine_ls_number_reflns         1630
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.049
_refine_ls_R_factor_all          0.0506
_refine_ls_R_factor_gt           0.0404
_refine_ls_shift/su_max          0
_refine_ls_shift/su_mean         0
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0577P)^2^+0.1596P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1032
_refine_ls_wR_factor_ref         0.1118
_reflns_number_gt                1323
_reflns_number_total             1630
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jo301859h_si_001.cif
_cod_data_source_block           ar105
_cod_database_code               4027677