#------------------------------------------------------------------------------
#$Date: 2016-03-26 14:15:18 +0200 (Sat, 26 Mar 2016) $
#$Revision: 180254 $
#$URL: svn://www.crystallography.net/cod/cif/7/11/40/7114063.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_7114063
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            'C13 H23 N O2'
_chemical_formula_weight         225.32
_chemical_name_systematic
;
1-(2,2-Dimethylpropionyl)azonan-2-one
;
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2yn'
_symmetry_space_group_name_H-M   'P 1 21/n 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL
_cell_angle_alpha                90.00
_cell_angle_beta                 94.201(14)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   10.462(2)
_cell_length_b                   22.892(5)
_cell_length_c                   5.5006(9)
_cell_measurement_temperature    293(2)
_cell_volume                     1313.8(4)
_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      293(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  0.0178
_diffrn_reflns_av_sigmaI/netI    0.0204
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       27
_diffrn_reflns_limit_k_min       0
_diffrn_reflns_limit_l_max       4
_diffrn_reflns_limit_l_min       -6
_diffrn_reflns_number            3322
_diffrn_reflns_theta_max         67.94
_diffrn_reflns_theta_min         3.86
_exptl_absorpt_coefficient_mu    0.598
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.139
_exptl_crystal_description       prismatic
_exptl_crystal_F_000             496
_exptl_crystal_size_max          0.5
_exptl_crystal_size_mid          0.3
_exptl_crystal_size_min          0.2
_refine_diff_density_max         0.275
_refine_diff_density_min         -0.189
_refine_diff_density_rms         0.041
_refine_ls_extinction_coef       0.0121(22)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_all   1.525
_refine_ls_goodness_of_fit_obs   1.559
_refine_ls_matrix_type           full
_refine_ls_number_parameters     146
_refine_ls_number_reflns         2390
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.601
_refine_ls_restrained_S_obs      1.559
_refine_ls_R_factor_all          0.0498
_refine_ls_R_factor_obs          0.0435
_refine_ls_shift/esd_max         -0.062
_refine_ls_shift/esd_mean        0.009
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.1000P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_all         0.1849
_refine_ls_wR_factor_obs         0.1698
_reflns_number_observed          2135
_reflns_number_total             2395
_reflns_observed_criterion       >2sigma(I)
_cod_data_source_file            b207925a.txt
_cod_data_source_block           shelxl_1c
_cod_depositor_comments
;
The following automatic conversions were performed:

'_refine_ls_weighting_scheme' value 'calc
w=1/[\s^2^(Fo^2^)+(0.1000P)^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^)+(0.1000P)^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      P21/n
_cod_database_code               7114063
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -y-1/2, z-1/2'
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 0.02471(10) 0.92193(5) 0.0267(2) 0.0414(3) Uani 1 d
O2 O 0.27909(10) 0.81591(5) -0.2247(2) 0.0481(4) Uani 1 d
N1 N 0.10154(10) 0.87080(4) -0.2874(2) 0.0283(3) Uani 1 d
C1 C 0.01348(12) 0.90823(5) -0.1874(2) 0.0304(4) Uani 1 d
C2 C -0.09429(13) 0.93246(6) -0.3539(3) 0.0370(4) Uani 1 d
C3 C -0.22837(14) 0.90744(7) -0.3181(3) 0.0443(4) Uani 1 d
C4 C -0.26229(14) 0.84874(8) -0.4385(3) 0.0521(5) Uani 1 d
C5 C -0.2399(2) 0.79474(8) -0.2793(4) 0.0576(5) Uani 1 d
C6 C -0.1047(2) 0.78260(7) -0.1715(3) 0.0503(5) Uani 1 d
C7 C -0.00243(15) 0.77247(6) -0.3520(3) 0.0423(4) Uani 1 d
C8 C 0.05183(12) 0.82654(6) -0.4678(2) 0.0331(4) Uani 1 d
C9 C 0.22829(12) 0.86238(5) -0.1900(2) 0.0306(4) Uani 1 d
C10 C 0.30784(13) 0.91280(6) -0.0710(2) 0.0335(4) Uani 1 d
C11 C 0.26563(15) 0.97356(6) -0.1625(3) 0.0405(4) Uani 1 d
C12 C 0.3067(2) 0.90869(8) 0.2071(3) 0.0522(5) Uani 1 d
C13 C 0.4460(2) 0.90299(7) -0.1360(3) 0.0460(4) Uani 1 d
H1 H -0.0800 0.9288 -0.5314 0.065 Uiso 1 d
H2 H -0.1000 0.9744 -0.3040 0.065 Uiso 1 d
H3 H -0.2400 0.9054 -0.1504 0.065 Uiso 1 d
H4 H -0.3000 0.9360 -0.3789 0.065 Uiso 1 d
H5 H -0.2200 0.8450 -0.5984 0.065 Uiso 1 d
H6 H -0.3400 0.8485 -0.4940 0.065 Uiso 1 d
H7 H -0.2600 0.7640 -0.3777 0.065 Uiso 1 d
H8 H -0.3000 0.7992 -0.1589 0.065 Uiso 1 d
H9 H -0.1000 0.7468 -0.0583 0.065 Uiso 1 d
H10 H -0.0800 0.8151 -0.0435 0.065 Uiso 1 d
H11 H 0.0600 0.7496 -0.2608 0.065 Uiso 1 d
H12 H -0.0400 0.7499 -0.4921 0.065 Uiso 1 d
H13 H 0.1200 0.8152 -0.5614 0.065 Uiso 1 d
H14 H -0.0200 0.8461 -0.5870 0.065 Uiso 1 d
H15 H 0.3400 1.0020 -0.1062 0.065 Uiso 1 d
H16 H 0.2600 0.9756 -0.3464 0.065 Uiso 1 d
H17 H 0.1800 0.9883 -0.1072 0.065 Uiso 1 d
H18 H 0.3600 0.9386 0.2812 0.065 Uiso 1 d
H19 H 0.3400 0.8740 0.2718 0.065 Uiso 1 d
H20 H 0.2200 0.9133 0.2625 0.065 Uiso 1 d
H21 H 0.5000 0.9344 -0.0539 0.065 Uiso 1 d
H22 H 0.4800 0.8658 -0.0687 0.065 Uiso 1 d
H23 H 0.4600 0.9018 -0.2782 0.065 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
C1 N1 C9 124.30(10)
C1 N1 C8 118.14(10)
C9 N1 C8 115.80(10)
O1 C1 N1 121.23(12)
O1 C1 C2 120.59(12)
N1 C1 C2 118.16(11)
C1 C2 C3 115.71(11)
C4 C3 C2 117.14(11)
C5 C4 C3 116.31(14)
C6 C5 C4 118.19(13)
C5 C6 C7 116.75(14)
C8 C7 C6 116.65(12)
N1 C8 C7 113.49(10)
O2 C9 N1 118.22(11)
O2 C9 C10 119.71(12)
N1 C9 C10 121.60(11)
C13 C10 C11 108.10(11)
C13 C10 C12 107.49(12)
C11 C10 C12 111.10(12)
C13 C10 C9 106.30(11)
C11 C10 C9 113.99(11)
C12 C10 C9 109.54(12)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
O1 C1 1.216(2)
O2 C9 1.211(2)
N1 C1 1.400(2)
N1 C9 1.407(2)
N1 C8 1.485(2)
C1 C2 1.505(2)
C2 C3 1.541(2)
C3 C4 1.528(2)
C4 C5 1.523(3)
C5 C6 1.519(3)
C6 C7 1.530(2)
C7 C8 1.521(2)
C9 C10 1.541(2)
C10 C13 1.531(2)
C10 C11 1.533(2)
C10 C12 1.533(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 -23.6(2)
C8 N1 C1 O1 140.59(12)
C9 N1 C1 C2 154.89(11)
C8 N1 C1 C2 -40.9(2)
O1 C1 C2 C3 -73.2(2)
N1 C1 C2 C3 108.29(13)
C1 C2 C3 C4 -81.5(2)
C2 C3 C4 C5 95.0(2)
C3 C4 C5 C6 -59.8(2)
C4 C5 C6 C7 -61.3(2)
C5 C6 C7 C8 79.3(2)
C1 N1 C8 C7 -80.69(14)
C9 N1 C8 C7 84.84(13)
C6 C7 C8 N1 53.4(2)
C1 N1 C9 O2 151.98(13)
C8 N1 C9 O2 -12.6(2)
C1 N1 C9 C10 -35.9(2)
C8 N1 C9 C10 159.59(11)
O2 C9 C10 C13 27.7(2)
N1 C9 C10 C13 -144.31(12)
O2 C9 C10 C11 146.69(13)
N1 C9 C10 C11 -25.3(2)
O2 C9 C10 C12 -88.1(2)
N1 C9 C10 C12 99.83(14)
