#------------------------------------------------------------------------------
#$Date: 2025-08-22 00:24:23 +0200 (Fri 22 de Aug de 2025) $
#$Revision: 301857 $
#$URL: svn://www.crystallography.net/cod/cif/7/11/40/7114064.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_7114064
loop_
_publ_author_name
'Yamada, Shinji'
'Homma, Akie'
_publ_section_title
;
 N-Substituent effect on the cis???trans geometry of nine-membered lactams
;
_journal_issue                   22
_journal_name_full               'Chemical Communications'
_journal_page_first              2656
_journal_paper_doi               10.1039/b207925a
_journal_year                    2002
_chemical_formula_sum            'C16 H21 N O3'
_chemical_formula_weight         275.34
_chemical_name_systematic
;
2-Oxoazonane-1-carboxylic acid benzyl ester
;
_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
_audit_creation_method           SHELXL
_cell_angle_alpha                96.600(14)
_cell_angle_beta                 99.012(15)
_cell_angle_gamma                103.634(11)
_cell_formula_units_Z            2
_cell_length_a                   8.2108(13)
_cell_length_b                   12.2287(15)
_cell_length_c                   7.602(2)
_cell_measurement_temperature    230(2)
_cell_volume                     723.4(2)
_computing_cell_refinement       'Rigaku afc7r'
_computing_data_collection       'Rigaku afc7r'
_computing_molecular_graphics    SHELXTL
_computing_structure_refinement  'SHELXL-93 (Sheldrick, 1993)'
_computing_structure_solution    'SHELXS-86 (Sheldrick, 1990)'
_diffrn_ambient_temperature      230(2)
_diffrn_measurement_device       'Rigaku afc7r'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0601
_diffrn_reflns_av_sigmaI/netI    0.0336
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       9
_diffrn_reflns_limit_l_min       -6
_diffrn_reflns_number            4655
_diffrn_reflns_theta_max         67.93
_diffrn_reflns_theta_min         3.77
_exptl_absorpt_coefficient_mu    0.701
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.264
_exptl_crystal_description       prismatic
_exptl_crystal_F_000             296
_exptl_crystal_size_max          0.5
_exptl_crystal_size_mid          0.35
_exptl_crystal_size_min          0.3
_refine_diff_density_max         0.244
_refine_diff_density_min         -0.220
_refine_diff_density_rms         0.040
_refine_ls_extinction_coef       0.0135(43)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_all   2.864
_refine_ls_goodness_of_fit_obs   2.896
_refine_ls_matrix_type           full
_refine_ls_number_parameters     182
_refine_ls_number_reflns         2617
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      3.090
_refine_ls_restrained_S_obs      2.896
_refine_ls_R_factor_all          0.0449
_refine_ls_R_factor_obs          0.0432
_refine_ls_shift/esd_max         0.041
_refine_ls_shift/esd_mean        0.010
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0584P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_all         0.2064
_refine_ls_wR_factor_obs         0.1907
_reflns_number_observed          2534
_reflns_number_total             2627
_reflns_observed_criterion       >2sigma(I)
_cod_data_source_file            b207925a.txt
_cod_data_source_block           shelxl_1d
_cod_depositor_comments
;
The following automatic conversions were performed:

'_refine_ls_weighting_scheme' value 'calc
w=1/[\s^2^(Fo^2^)+(0.0584P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3' was
changed to 'calc'. New tag '_refine_ls_weighting_details' was
created. The value of the new tag was set to
'w=1/[\s^2^(Fo^2^)+(0.0584P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3'.

Automatic conversion script
Id: cif_fix_values 3143 2015-03-26 13:38:13Z robertas 
;
_cod_original_sg_symbol_H-M      P-1
_cod_database_code               7114064
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -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_thermal_displace_type
_atom_site_occupancy
_atom_site_calc_flag
O1 O 0.32200(14) 0.92029(9) 0.69016(14) 0.0424(4) Uani 1 d
O2 O 0.79186(12) 0.93118(9) 0.64720(12) 0.0374(3) Uani 1 d
O3 O 0.70063(11) 0.82848(8) 0.36849(12) 0.0325(3) Uani 1 d
N1 N 0.50543(13) 0.86344(9) 0.52737(13) 0.0279(3) Uani 1 d
C1 C 0.4488(2) 0.88594(11) 0.6915(2) 0.0316(4) Uani 1 d
C2 C 0.5340(2) 0.84892(14) 0.8566(2) 0.0397(4) Uani 1 d
C3 C 0.4437(2) 0.72432(14) 0.8625(2) 0.0408(4) Uani 1 d
C4 C 0.4594(2) 0.63530(14) 0.7077(2) 0.0422(4) Uani 1 d
C5 C 0.2918(2) 0.57508(13) 0.5770(2) 0.0451(4) Uani 1 d
C6 C 0.2053(2) 0.64795(12) 0.4631(2) 0.0376(4) Uani 1 d
C7 C 0.3020(2) 0.69839(12) 0.3201(2) 0.0344(4) Uani 1 d
C8 C 0.3758(2) 0.82674(11) 0.3593(2) 0.0302(4) Uani 1 d
C9 C 0.6774(2) 0.87839(10) 0.5247(2) 0.0282(4) Uani 1 d
C10 C 0.8776(2) 0.85742(13) 0.3440(2) 0.0397(4) Uani 1 d
C11 C 0.8901(2) 0.78455(11) 0.1769(2) 0.0306(4) Uani 1 d
C12 C 0.8199(2) 0.66743(13) 0.1467(2) 0.0397(4) Uani 1 d
C13 C 0.8407(2) 0.60173(15) -0.0053(3) 0.0547(5) Uani 1 d
C14 C 0.9284(2) 0.6529(2) -0.1288(2) 0.0578(6) Uani 1 d
C15 C 0.9962(2) 0.7684(2) -0.0998(2) 0.0499(5) Uani 1 d
C16 C 0.9780(2) 0.83433(13) 0.0522(2) 0.0382(4) Uani 1 d
H1 H 0.5203 0.9000 0.9596 0.058 Uiso 1 d
H2 H 0.6449 0.8400 0.8495 0.058 Uiso 1 d
H3 H 0.3272 0.7200 0.8627 0.058 Uiso 1 d
H4 H 0.4889 0.7000 0.9717 0.058 Uiso 1 d
H5 H 0.5017 0.5800 0.7661 0.058 Uiso 1 d
H6 H 0.5448 0.6800 0.6385 0.058 Uiso 1 d
H7 H 0.2177 0.5400 0.6513 0.058 Uiso 1 d
H8 H 0.3159 0.5200 0.4975 0.058 Uiso 1 d
H9 H 0.1822 0.7000 0.5390 0.058 Uiso 1 d
H10 H 0.0906 0.6000 0.3966 0.058 Uiso 1 d
H11 H 0.2329 0.6800 0.2084 0.058 Uiso 1 d
H12 H 0.3947 0.6600 0.3081 0.058 Uiso 1 d
H13 H 0.2913 0.8600 0.3751 0.058 Uiso 1 d
H14 H 0.4301 0.8600 0.2601 0.058 Uiso 1 d
H15 H 0.9198 0.9400 0.3339 0.058 Uiso 1 d
H16 H 0.9405 0.8400 0.4490 0.058 Uiso 1 d
H17 H 0.7515 0.6400 0.2308 0.058 Uiso 1 d
H18 H 0.7933 0.5200 -0.0247 0.058 Uiso 1 d
H19 H 0.9390 0.6000 -0.2354 0.058 Uiso 1 d
H20 H 1.0573 0.8000 -0.1905 0.058 Uiso 1 d
H21 H 1.0250 0.9200 0.0642 0.058 Uiso 1 d
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
C9 O3 C10 113.85(9)
C9 N1 C1 120.84(11)
C9 N1 C8 121.15(9)
C1 N1 C8 117.99(10)
O1 C1 N1 119.44(12)
O1 C1 C2 121.95(12)
N1 C1 C2 117.94(11)
C1 C2 C3 109.19(12)
C2 C3 C4 115.54(11)
C5 C4 C3 114.99(12)
C6 C5 C4 117.45(12)
C5 C6 C7 115.71(12)
C8 C7 C6 114.83(11)
N1 C8 C7 112.41(10)
O2 C9 O3 124.42(11)
O2 C9 N1 124.48(11)
O3 C9 N1 111.10(10)
O3 C10 C11 108.45(10)
C12 C11 C16 119.27(13)
C12 C11 C10 121.22(12)
C16 C11 C10 119.48(12)
C13 C12 C11 119.73(14)
C12 C13 C14 120.2(2)
C15 C14 C13 120.00(14)
C14 C15 C16 120.2(2)
C15 C16 C11 120.53(14)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
O1 C1 1.210(2)
O2 C9 1.212(2)
O3 C9 1.333(2)
O3 C10 1.4591(14)
N1 C9 1.384(2)
N1 C1 1.418(2)
N1 C8 1.478(2)
C1 C2 1.508(2)
C2 C3 1.538(2)
C3 C4 1.551(2)
C4 C5 1.533(2)
C5 C6 1.527(2)
C6 C7 1.545(2)
C7 C8 1.519(2)
C10 C11 1.497(2)
C11 C12 1.389(2)
C11 C16 1.389(2)
C12 C13 1.387(2)
C13 C14 1.387(3)
C14 C15 1.368(3)
C15 C16 1.380(2)
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
C9 N1 C1 O1 148.33(13)
C8 N1 C1 O1 -30.0(2)
C9 N1 C1 C2 -40.9(2)
C8 N1 C1 C2 140.78(12)
O1 C1 C2 C3 84.0(2)
N1 C1 C2 C3 -86.58(14)
C1 C2 C3 C4 65.30(15)
C2 C3 C4 C5 -113.52(14)
C3 C4 C5 C6 64.7(2)
C4 C5 C6 C7 67.2(2)
C5 C6 C7 C8 -110.50(14)
C9 N1 C8 C7 93.71(13)
C1 N1 C8 C7 -87.95(13)
C6 C7 C8 N1 62.52(13)
C10 O3 C9 O2 -9.2(2)
C10 O3 C9 N1 169.91(11)
C1 N1 C9 O2 -15.3(2)
C8 N1 C9 O2 162.94(12)
C1 N1 C9 O3 165.56(11)
C8 N1 C9 O3 -16.16(15)
C9 O3 C10 C11 172.50(11)
O3 C10 C11 C12 -48.8(2)
O3 C10 C11 C16 133.11(12)
C16 C11 C12 C13 1.1(2)
C10 C11 C12 C13 -176.97(13)
C11 C12 C13 C14 -1.3(2)
C12 C13 C14 C15 0.6(2)
C13 C14 C15 C16 0.1(2)
C14 C15 C16 C11 -0.3(2)
C12 C11 C16 C15 -0.3(2)
C10 C11 C16 C15 177.77(13)
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 PubChem 101169612
