#------------------------------------------------------------------------------
#$Date: 2016-02-19 16:29:56 +0200 (Fri, 19 Feb 2016) $
#$Revision: 176759 $
#$URL: svn://www.crystallography.net/cod/cif/2/00/87/2008775.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_2008775
loop_
_publ_author_name
'Zwege, Daniel'
'Thompson, Hugh W.'
'Brunskill, Andrew P. J.'
'Lalancette, Roger A.'
_publ_section_title
;
 (+/-)-2-Aza-3,9-dioxotricyclo[4.4.4.0^1,6^]tetradecane: dimeric and
 catemeric hydrogen bonding in two polymorphs of a propellanoid keto
 lactam
;
_journal_issue                   8
_journal_name_full               'Acta Crystallographica Section C'
_journal_page_first              1370
_journal_page_last               1373
_journal_paper_doi               10.1107/S0108270199004485
_journal_volume                  55
_journal_year                    1999
_chemical_formula_sum            'C13 H19 N O2'
_chemical_formula_weight         221.29
_chemical_melting_point          462
_chemical_name_systematic
;
(+-)-2-Aza-3,9-dioxotricyclo[4.4.4.0^1,6^]tetradecane
;
_space_group_IT_number           15
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-C 2yc'
_symmetry_space_group_name_H-M   'C 1 2/c 1'
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 101.090(10)
_cell_angle_gamma                90.00
_cell_formula_units_Z            8
_cell_length_a                   11.966(3)
_cell_length_b                   8.6020(10)
_cell_length_c                   23.688(3)
_cell_measurement_reflns_used    31
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      12.38
_cell_measurement_theta_min      2.91
_cell_volume                     2392.7(7)
_computing_cell_refinement       'XSCANS (Siemens,  1996)'
_computing_data_collection       'XSCANS (Fait, 1991)'
_computing_data_reduction        XSCANS
_computing_molecular_graphics    SHELXL97
_computing_publication_material  SHELXL97
_computing_structure_refinement  'SHELXL97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 1997)'
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 1.00
_diffrn_measured_fraction_theta_max 1.00
_diffrn_measurement_device       'Siemens P4'
_diffrn_measurement_method       '2θ/θ scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'normal-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.051
_diffrn_reflns_av_sigmaI/netI    0.084
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -1
_diffrn_reflns_limit_l_max       28
_diffrn_reflns_limit_l_min       -1
_diffrn_reflns_number            2809
_diffrn_reflns_theta_full        25.00
_diffrn_reflns_theta_max         25.00
_diffrn_reflns_theta_min         1.75
_diffrn_standards_decay_%        'No decay. Variation < 1'
_diffrn_standards_interval_count 97
_diffrn_standards_number         3
_exptl_absorpt_coefficient_mu    0.082
_exptl_absorpt_correction_T_max  0.982
_exptl_absorpt_correction_T_min  0.971
_exptl_absorpt_correction_type   numerical
_exptl_absorpt_process_details   '(XPREP; Sheldrick, 1997)'
_exptl_crystal_colour            'Pale yellow'
_exptl_crystal_density_diffrn    1.229
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       'Rectangular prism'
_exptl_crystal_F_000             960
_exptl_crystal_size_max          0.80
_exptl_crystal_size_mid          0.30
_exptl_crystal_size_min          0.20
_refine_diff_density_max         0.184
_refine_diff_density_min         -0.142
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.01
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     149
_refine_ls_number_reflns         2115
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.01
_refine_ls_R_factor_all          0.149
_refine_ls_R_factor_gt           0.065
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w = 1/[σ²(Fo²)+(0.0526P)²+1.1209P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_ref         0.162
_reflns_number_gt                1038
_reflns_number_total             2115
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            fg1543.cif
_cod_data_source_block           I
_cod_depositor_comments
;
The following automatic conversions were performed:
'_symmetry_cell_setting' value 'Monoclinic' changed to 'monoclinic'
according to '/home/saulius/struct/CIF-dictionaries/cif_core.dic'
dictionary named 'cif_core.dic' version 2.4.1 from 2010-06-29.

Automatic conversion script
Id: cif_fix_enum 1527 2010-12-29 10:47:43Z saulius 

The following automatic conversions were performed:

'_symmetry_cell_setting' value 'Monoclinic' changed to 'monoclinic'
according to /home/saulius/struct/CIF-dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.1 from 2010-06-29.

Automatic conversion script
Id: cif_fix_values 1715 2011-07-08 13:25:40Z adriana 
;
_cod_original_sg_symbol_H-M      'C 2/c'
_cod_database_code               2008775
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y, -z+1/2'
'x+1/2, y+1/2, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y, z-1/2'
'-x+1/2, -y+1/2, -z'
'x+1/2, -y+1/2, z-1/2'
loop_
_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
_atom_site_type_symbol
O1 0.8454(2) 0.2532(3) 0.21049(10) 0.0774(9) Uani d . 1 . . O
O2 0.9943(2) -0.1670(4) 0.44663(12) 0.0879(10) Uani d . 1 . . O
C1 0.9075(3) 0.1648(4) 0.36288(12) 0.0452(9) Uani d . 1 . . C
N2 0.9121(2) 0.2221(4) 0.30475(11) 0.0546(8) Uani d . 1 . . N
C3 0.8279(3) 0.2244(4) 0.25934(15) 0.0567(10) Uani d . 1 . . C
C4 0.7086(3) 0.2031(5) 0.26913(14) 0.0713(13) Uani d . 1 . . C
C5 0.6968(3) 0.1391(5) 0.32784(13) 0.0578(10) Uani d . 1 . . C
C6 0.7884(3) 0.1973(4) 0.37706(13) 0.0419(8) Uani d . 1 . . C
C7 0.7788(3) 0.1130(4) 0.43343(13) 0.0521(10) Uani d . 1 . . C
C8 0.8077(3) -0.0593(5) 0.43563(16) 0.0664(12) Uani d . 1 . . C
C9 0.9191(3) -0.0877(5) 0.41887(16) 0.0625(11) Uani d . 1 . . C
C10 0.9323(3) -0.0111(4) 0.36378(13) 0.0581(10) Uani d . 1 . . C
C11 1.0012(3) 0.2473(5) 0.40488(14) 0.0667(12) Uani d . 1 . . C
C12 0.9812(4) 0.4189(6) 0.40965(19) 0.0922(16) Uani d . 1 . . C
C13 0.8681(4) 0.4499(5) 0.42690(18) 0.0914(15) Uani d . 1 . . C
C14 0.7727(3) 0.3727(4) 0.38566(16) 0.0672(11) Uani d . 1 . . C
H2 0.9766 0.2580 0.2997 0.060(11) Uiso calc R 1 . . H
H4A 0.6689 0.1335 0.2397 0.085(7) Uiso calc R 1 . . H
H4B 0.6702 0.3029 0.2638 0.085(7) Uiso calc R 1 . . H
H5A 0.6227 0.1680 0.3354 0.085(7) Uiso calc R 1 . . H
H5B 0.7001 0.0265 0.3267 0.085(7) Uiso calc R 1 . . H
H7A 0.8290 0.1644 0.4650 0.066(4) Uiso calc R 1 . . H
H7B 0.7016 0.1250 0.4397 0.066(4) Uiso calc R 1 . . H
H8A 0.8101 -0.0980 0.4743 0.066(4) Uiso calc R 1 . . H
H8B 0.7487 -0.1156 0.4098 0.066(4) Uiso calc R 1 . . H
H10A 0.8810 -0.0602 0.3321 0.066(4) Uiso calc R 1 . . H
H10B 1.0095 -0.0272 0.3579 0.066(4) Uiso calc R 1 . . H
H11A 1.0072 0.2005 0.4426 0.085(4) Uiso calc R 1 . . H
H11B 1.0731 0.2315 0.3926 0.085(4) Uiso calc R 1 . . H
H12A 0.9824 0.4683 0.3730 0.085(4) Uiso calc R 1 . . H
H12B 1.0419 0.4637 0.4381 0.085(4) Uiso calc R 1 . . H
H13B 0.8699 0.4105 0.4654 0.085(4) Uiso calc R 1 . . H
H13C 0.8547 0.5610 0.4272 0.085(4) Uiso calc R 1 . . H
H14B 0.7647 0.4238 0.3486 0.085(4) Uiso calc R 1 . . H
H14C 0.7023 0.3885 0.3995 0.085(4) Uiso calc R 1 . . H
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 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 '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
N2 C1 C11 107.4(3)
N2 C1 C10 107.4(3)
C11 C1 C10 109.4(3)
N2 C1 C6 110.1(3)
C11 C1 C6 111.5(3)
C10 C1 C6 110.9(3)
C3 N2 C1 127.1(3)
O1 C3 N2 121.5(3)
O1 C3 C4 120.3(3)
N2 C3 C4 118.0(3)
C3 C4 C5 116.2(3)
C6 C5 C4 113.6(3)
C5 C6 C14 109.6(3)
C5 C6 C7 110.2(3)
C14 C6 C7 108.4(3)
C5 C6 C1 109.3(3)
C14 C6 C1 110.2(3)
C7 C6 C1 109.1(3)
C8 C7 C6 115.7(3)
C9 C8 C7 111.2(3)
O2 C9 C8 123.9(4)
O2 C9 C10 121.8(4)
C8 C9 C10 114.3(3)
C9 C10 C1 113.1(3)
C12 C11 C1 113.5(4)
C11 C12 C13 110.9(3)
C14 C13 C12 110.7(3)
C13 C14 C6 114.9(3)
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
O1 C3 . 1.240(4) y
O2 C9 . 1.216(4) y
C1 N2 . 1.474(4) y
C1 C11 . 1.523(4) ?
C1 C10 . 1.541(5) ?
C1 C6 . 1.551(4) ?
N2 C3 . 1.325(4) y
C3 C4 . 1.501(5) ?
C4 C5 . 1.527(4) ?
C5 C6 . 1.523(4) ?
C6 C14 . 1.539(5) ?
C6 C7 . 1.543(4) ?
C7 C8 . 1.521(5) ?
C8 C9 . 1.483(5) ?
C9 C10 . 1.497(5) ?
C11 C12 . 1.503(6) ?
C12 C13 . 1.511(5) ?
C13 C14 . 1.506(5) ?
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
C11 C1 N2 C3 -155.5(4)
C10 C1 N2 C3 86.9(4)
C6 C1 N2 C3 -33.9(5)
C1 N2 C3 O1 -169.0(3)
C1 N2 C3 C4 15.7(6)
O1 C3 C4 C5 169.2(4)
N2 C3 C4 C5 -15.4(5)
C3 C4 C5 C6 36.2(5)
C4 C5 C6 C14 67.4(4)
C4 C5 C6 C7 -173.4(3)
C4 C5 C6 C1 -53.6(4)
N2 C1 C6 C5 50.1(4)
C11 C1 C6 C5 169.2(3)
C10 C1 C6 C5 -68.6(3)
N2 C1 C6 C14 -70.4(3)
C11 C1 C6 C14 48.7(4)
C10 C1 C6 C14 170.9(3)
N2 C1 C6 C7 170.7(3)
C11 C1 C6 C7 -70.2(4)
C10 C1 C6 C7 52.0(3)
C5 C6 C7 C8 67.8(4)
C14 C6 C7 C8 -172.2(3)
C1 C6 C7 C8 -52.2(4)
C6 C7 C8 C9 50.8(4)
C7 C8 C9 O2 130.5(4)
C7 C8 C9 C10 -49.9(4)
O2 C9 C10 C1 -127.1(4)
C8 C9 C10 C1 53.3(4)
N2 C1 C10 C9 -174.4(3)
C11 C1 C10 C9 69.3(4)
C6 C1 C10 C9 -54.1(4)
N2 C1 C11 C12 67.0(4)
C10 C1 C11 C12 -176.7(3)
C6 C1 C11 C12 -53.7(4)
C1 C11 C12 C13 56.8(4)
C11 C12 C13 C14 -55.4(5)
C12 C13 C14 C6 54.2(5)
C5 C6 C14 C13 -171.0(3)
C7 C6 C14 C13 68.6(4)
C1 C6 C14 C13 -50.7(4)
