#------------------------------------------------------------------------------
#$Date: 2017-10-13 14:42:48 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201982 $
#$URL: file:///home/coder/svn-repositories/cod/cif/4/02/76/4027679.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/
#
# All data on this site have been placed in the public domain by the
# contributors.
#
data_4027679
loop_
_publ_author_name
'Agnieszka Witosińska'
'Bogdan Musielak'
'Paweł Serda'
'Maria Owińska'
'Barbara Rys'
_publ_contact_author_address
;
Faculty of Chemistry
Jagiellonian University
Ingardena 3
30-060 Kraków, 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         'C12 H15 N O'
_chemical_formula_sum            'C12 H15 N O'
_chemical_formula_weight         189.25
_chemical_name_common            a99me
_chemical_name_systematic
;
2-methyl-1,4,5,6-tetrahydro-2H-benzo[c]azocin-3-one
;
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_Int_Tables_number      14
_symmetry_space_group_name_Hall  '-P 2yab'
_symmetry_space_group_name_H-M   'P 1 21/a 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             2012-08-16T18:31:16-00:00
_audit_creation_method           'WinGX routine CIF_UPDATE'
_cell_angle_alpha                90
_cell_angle_beta                 115.6650(10)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   12.0179(4)
_cell_length_b                   7.8710(3)
_cell_length_c                   12.0993(6)
_cell_measurement_reflns_used    3506
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      25.35
_cell_measurement_theta_min      2.91
_cell_measurement_wavelength     0.71073
_cell_volume                     1031.59(7)
_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 0.992
_diffrn_measured_fraction_theta_max 0.992
_diffrn_measurement_device       '95mm CCD camera on κ-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      0.25386E-2
_diffrn_orient_matrix_UB_12      -0.922784E-1
_diffrn_orient_matrix_UB_13      0.8335E-3
_diffrn_orient_matrix_UB_21      -0.11537E-2
_diffrn_orient_matrix_UB_22      0.11141E-2
_diffrn_orient_matrix_UB_23      0.127038
_diffrn_orient_matrix_UB_31      -0.815225E-1
_diffrn_orient_matrix_UB_32      -0.419771E-1
_diffrn_orient_matrix_UB_33      -0.3909E-3
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0342
_diffrn_reflns_av_unetI/netI     0.031
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            6971
_diffrn_reflns_theta_full        25.31
_diffrn_reflns_theta_max         25.31
_diffrn_reflns_theta_min         3.4
_diffrn_source                   'Enraf Nonius FR590'
_exptl_absorpt_coefficient_mu    0.077
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            white
_exptl_crystal_density_diffrn    1.219
_exptl_crystal_description       prism
_exptl_crystal_F_000             408
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.1
_refine_diff_density_max         0.144
_refine_diff_density_min         -0.187
_refine_diff_density_rms         0.031
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.065
_refine_ls_hydrogen_treatment    refall
_refine_ls_matrix_type           full
_refine_ls_number_parameters     187
_refine_ls_number_reflns         1877
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.065
_refine_ls_R_factor_all          0.0643
_refine_ls_R_factor_gt           0.0445
_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/[σ²(Fo²)+(0.0490P)²+0.2378P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1027
_refine_ls_wR_factor_ref         0.1162
_reflns_number_gt                1449
_reflns_number_total             1877
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jo301859h_si_003.cif
_cod_data_source_block           a99
_cod_database_code               4027679
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, y+1/2, -z'
'-x, -y, -z'
'x-1/2, -y-1/2, z'
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_multiplicity
_atom_site_calc_flag
N1 N 0.09918(12) 0.17022(17) 0.84083(12) 0.0430(4) Uani 1 1 d
C2 C 0.21875(14) 0.1741(2) 0.86223(14) 0.0436(4) Uani 1 1 d
O3 O 0.26432(12) 0.30159(16) 0.83939(13) 0.0630(4) Uani 1 1 d
C4 C 0.29931(17) 0.0206(2) 0.91852(17) 0.0508(5) Uani 1 1 d
C5 C 0.29260(17) -0.1183(3) 0.8273(2) 0.0571(5) Uani 1 1 d
C6 C 0.18760(19) -0.2471(2) 0.7946(2) 0.0586(5) Uani 1 1 d
C7 C 0.06143(17) -0.1946(2) 0.70020(16) 0.0501(4) Uani 1 1 d
C8 C 0.0146(2) -0.2649(3) 0.5828(2) 0.0696(6) Uani 1 1 d
C9 C -0.1017(2) -0.2233(4) 0.4946(2) 0.0821(8) Uani 1 1 d
C10 C -0.1753(2) -0.1146(4) 0.5213(2) 0.0772(7) Uani 1 1 d
C11 C -0.13117(18) -0.0425(3) 0.63702(19) 0.0596(5) Uani 1 1 d
C12 C -0.01326(15) -0.0799(2) 0.72607(15) 0.0453(4) Uani 1 1 d
C13 C 0.03459(16) 0.0140(2) 0.84624(16) 0.0462(4) Uani 1 1 d
C14 C 0.02029(19) 0.3135(3) 0.7772(2) 0.0553(5) Uani 1 1 d
H104 H 0.2788(17) -0.027(2) 0.9820(18) 0.061(5) Uiso 1 1 d
H113 H 0.0919(17) -0.057(2) 0.9148(17) 0.056(5) Uiso 1 1 d
H213 H -0.0337(17) 0.050(2) 0.8641(16) 0.051(5) Uiso 1 1 d
H205 H 0.375(2) -0.188(3) 0.8688(19) 0.074(6) Uiso 1 1 d
H204 H 0.3874(19) 0.069(2) 0.9553(18) 0.067(6) Uiso 1 1 d
H11 H -0.1839(19) 0.035(3) 0.6565(19) 0.074(6) Uiso 1 1 d
H206 H 0.2113(19) -0.347(3) 0.7686(19) 0.071(6) Uiso 1 1 d
H105 H 0.2887(19) -0.065(3) 0.750(2) 0.074(6) Uiso 1 1 d
H8 H 0.068(2) -0.344(3) 0.564(2) 0.090(7) Uiso 1 1 d
H106 H 0.1831(18) -0.281(3) 0.8742(19) 0.068(6) Uiso 1 1 d
H10 H -0.257(2) -0.079(3) 0.466(2) 0.093(8) Uiso 1 1 d
H314 H 0.062(2) 0.421(4) 0.793(2) 0.108(9) Uiso 1 1 d
H214 H -0.012(2) 0.293(3) 0.687(2) 0.094(8) Uiso 1 1 d
H114 H -0.050(3) 0.324(4) 0.798(3) 0.112(9) Uiso 1 1 d
H9 H -0.132(2) -0.282(4) 0.417(3) 0.111(9) Uiso 1 1 d
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 0.0413(7) 0.0398(7) 0.0477(7) -0.0010(6) 0.0192(6) 0.0007(5)
C2 0.0440(9) 0.0439(9) 0.0434(9) -0.0076(7) 0.0195(7) -0.0026(7)
O3 0.0571(8) 0.0496(7) 0.0887(10) 0.0007(7) 0.0375(7) -0.0075(6)
C4 0.0435(10) 0.0546(11) 0.0486(10) -0.0013(8) 0.0146(8) 0.0029(8)
C5 0.0524(11) 0.0517(11) 0.0677(12) -0.0027(9) 0.0265(9) 0.0084(8)
C6 0.0711(13) 0.0384(9) 0.0693(13) -0.0015(9) 0.0333(10) 0.0069(9)
C7 0.0588(11) 0.0424(9) 0.0552(10) -0.0044(8) 0.0304(8) -0.0121(8)
C8 0.0776(15) 0.0705(14) 0.0697(13) -0.0246(11) 0.0403(12) -0.0222(11)
C9 0.0846(17) 0.1030(19) 0.0590(13) -0.0275(13) 0.0315(12) -0.0376(15)
C10 0.0570(13) 0.1027(18) 0.0605(13) -0.0070(13) 0.0148(11) -0.0236(13)
C11 0.0468(11) 0.0667(13) 0.0629(12) -0.0026(10) 0.0216(9) -0.0133(9)
C12 0.0480(10) 0.0447(9) 0.0471(9) 0.0008(7) 0.0243(7) -0.0109(7)
C13 0.0466(10) 0.0482(10) 0.0505(10) 0.0012(8) 0.0272(8) -0.0022(8)
C14 0.0500(11) 0.0469(11) 0.0664(13) 0.0027(9) 0.0228(9) 0.0083(8)
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 0 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.006 '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'
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
C2 N1 C14 118.68(15)
C2 N1 C13 123.40(14)
C14 N1 C13 115.75(14)
O3 C2 N1 121.13(15)
O3 C2 C4 119.46(15)
N1 C2 C4 119.38(15)
C2 C4 C5 114.98(15)
C6 C5 C4 116.06(17)
C7 C6 C5 117.38(16)
C8 C7 C12 117.91(19)
C8 C7 C6 119.48(19)
C12 C7 C6 122.60(16)
C9 C8 C7 121.3(2)
C10 C9 C8 120.5(2)
C9 C10 C11 119.4(2)
C10 C11 C12 120.8(2)
C11 C12 C7 120.00(17)
C11 C12 C13 118.64(17)
C7 C12 C13 121.23(15)
N1 C13 C12 110.83(13)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
N1 C2 1.346(2)
N1 C14 1.460(2)
N1 C13 1.471(2)
C2 O3 1.231(2)
C2 C4 1.513(2)
C4 C5 1.531(3)
C5 C6 1.531(3)
C6 C7 1.508(3)
C7 C8 1.396(3)
C7 C12 1.401(2)
C8 C9 1.381(3)
C9 C10 1.367(4)
C10 C11 1.386(3)
C11 C12 1.390(3)
C12 C13 1.506(2)
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 30659561
