#------------------------------------------------------------------------------
#$Date: 2016-03-24 01:36:29 +0100 (jue 24 de mar de 2016) $
#$Revision: 179588 $
#$URL: svn://www.crystallography.net/cod/cif/4/50/53/4505314.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_4505314
loop_
_publ_author_name
'Brewer, Jason T.'
'Parkin, Sean'
'Grossman, Robert B.'
_publ_section_title
;
 A Systematic Study of the Relationship between Molecular and Crystal
 Structure among 3,5-Diazabicyclo[2.2.2]octane-2,6-diones
;
_journal_issue                   3
_journal_name_full               'Crystal Growth & Design'
_journal_page_first              591
_journal_paper_doi               10.1021/cg0341609
_journal_volume                  4
_journal_year                    2004
_chemical_formula_sum            'C7 H10 N2 O2'
_chemical_formula_weight         154.17
_chemical_name_systematic
; 
 ? 
;
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_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_creation_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 94.5650(13)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   9.7000(3)
_cell_length_b                   7.4300(2)
_cell_length_c                   9.9090(4)
_cell_measurement_reflns_used    1714
_cell_measurement_temperature    90.0(2)
_cell_measurement_theta_max      27.48
_cell_measurement_theta_min      1.00
_cell_volume                     711.89(4)
_computing_cell_refinement       'SCALEPACK (Otwinowski & Minor, 1997)'
_computing_data_collection       'COLLECT (Nonius, 1998)'
_computing_data_reduction        'DENZO-SMN (Otwinowski & Minor, 1997)'
_computing_molecular_graphics    'XP in Siemens SHELXTL (Sheldrick, 1994)'
_computing_publication_material
;
SHELX97-2 (Sheldrick, 1997) and local procedures
;
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      90.0(2)
_diffrn_detector_area_resol_mean 18
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type  'Nonius KappaCCD diffractometer'
_diffrn_measurement_method       'ω scans at fixed χ = 55°'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0199
_diffrn_reflns_av_sigmaI/netI    0.0318
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            3100
_diffrn_reflns_theta_full        27.49
_diffrn_reflns_theta_max         27.49
_diffrn_reflns_theta_min         2.11
_diffrn_standards_decay_%        <1
_exptl_absorpt_coefficient_mu    0.107
_exptl_absorpt_correction_T_max  0.9915
_exptl_absorpt_correction_T_min  0.9634
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'Scalepack (Otwinowski & Minor, 1997)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.438
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             328
_exptl_crystal_size_max          0.35
_exptl_crystal_size_mid          0.30
_exptl_crystal_size_min          0.08
_refine_diff_density_max         0.289
_refine_diff_density_min         -0.321
_refine_diff_density_rms         0.054
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.045
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     101
_refine_ls_number_reflns         1631
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.045
_refine_ls_R_factor_all          0.0508
_refine_ls_R_factor_gt           0.0402
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0653P)²+0.2126P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1064
_refine_ls_wR_factor_ref         0.1134
_reflns_number_gt                1343
_reflns_number_total             1631
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            cg0341609si20030822_115801.cif
_cod_data_source_block           2g
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               4505314
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -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_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
C1 C 0.29113(13) 0.12932(17) 0.16111(13) 0.0147(3) Uani 1 1 d .
H1 H 0.3155 0.2484 0.2036 0.018 Uiso 1 1 calc R
O2 O 0.06935(10) 0.15366(13) 0.25971(10) 0.0206(3) Uani 1 1 d .
C2 C 0.14789(13) 0.06696(18) 0.19257(13) 0.0147(3) Uani 1 1 d .
N3 N 0.11929(11) -0.09510(15) 0.13760(11) 0.0147(3) Uani 1 1 d .
H3 H 0.0393 -0.1488 0.1449 0.018 Uiso 1 1 calc R
C4 C 0.22910(13) -0.17792(18) 0.06453(13) 0.0142(3) Uani 1 1 d .
N5 N 0.35614(11) -0.17620(15) 0.15544(11) 0.0146(3) Uani 1 1 d .
H5 H 0.4053 -0.2742 0.1729 0.018 Uiso 1 1 calc R
O6 O 0.49668(9) 0.00683(13) 0.28962(10) 0.0187(3) Uani 1 1 d .
C6 C 0.39291(13) -0.01720(17) 0.21010(13) 0.0139(3) Uani 1 1 d .
C7 C 0.29131(14) 0.13610(19) 0.00406(14) 0.0180(3) Uani 1 1 d .
H7A H 0.2229 0.2257 -0.0331 0.022 Uiso 1 1 calc R
H7B H 0.3838 0.1726 -0.0217 0.022 Uiso 1 1 calc R
C8 C 0.25423(14) -0.05220(19) -0.05460(13) 0.0172(3) Uani 1 1 d .
H8A H 0.1700 -0.0450 -0.1177 0.021 Uiso 1 1 calc R
H8B H 0.3309 -0.0988 -0.1048 0.021 Uiso 1 1 calc R
C9 C 0.19124(14) -0.36855(19) 0.02285(15) 0.0187(3) Uani 1 1 d .
H9A H 0.1716 -0.4384 0.1030 0.028 Uiso 1 1 calc R
H9B H 0.2685 -0.4238 -0.0200 0.028 Uiso 1 1 calc R
H9C H 0.1091 -0.3669 -0.0415 0.028 Uiso 1 1 calc R
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
C1 0.0157(6) 0.0126(6) 0.0157(6) -0.0001(5) 0.0010(5) -0.0004(5)
O2 0.0185(5) 0.0219(6) 0.0220(5) -0.0046(4) 0.0049(4) 0.0045(4)
C2 0.0156(6) 0.0158(6) 0.0124(6) 0.0018(5) -0.0005(5) 0.0021(5)
N3 0.0125(5) 0.0155(6) 0.0164(6) -0.0017(4) 0.0033(4) -0.0012(4)
C4 0.0126(6) 0.0151(6) 0.0149(6) -0.0020(5) 0.0009(5) 0.0004(5)
N5 0.0143(5) 0.0123(5) 0.0168(6) -0.0008(4) -0.0010(4) 0.0024(4)
O6 0.0164(5) 0.0175(5) 0.0213(5) 0.0003(4) -0.0035(4) -0.0020(4)
C6 0.0127(6) 0.0157(6) 0.0138(6) 0.0008(5) 0.0037(5) -0.0015(5)
C7 0.0197(7) 0.0174(7) 0.0171(7) 0.0037(5) 0.0034(5) -0.0010(5)
C8 0.0171(6) 0.0203(7) 0.0144(6) 0.0000(5) 0.0028(5) -0.0004(5)
C9 0.0196(7) 0.0163(7) 0.0199(7) -0.0035(5) 0.0008(5) -0.0013(5)
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'
N N 0.0061 0.0033 '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'
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
C2 C1 C6 107.25(10)
C2 C1 C7 106.77(11)
C6 C1 C7 106.83(11)
C2 C1 H1 111.9
C6 C1 H1 111.9
C7 C1 H1 111.9
O2 C2 N3 124.87(12)
O2 C2 C1 124.45(12)
N3 C2 C1 110.68(11)
C2 N3 C4 116.19(10)
C2 N3 H3 121.9
C4 N3 H3 121.9
N5 C4 N3 107.46(10)
N5 C4 C9 110.46(10)
N3 C4 C9 110.91(11)
N5 C4 C8 106.79(10)
N3 C4 C8 106.78(10)
C9 C4 C8 114.11(11)
C6 N5 C4 116.14(11)
C6 N5 H5 121.9
C4 N5 H5 121.9
O6 C6 N5 124.15(12)
O6 C6 C1 124.90(11)
N5 C6 C1 110.94(11)
C8 C7 C1 109.13(11)
C8 C7 H7A 109.9
C1 C7 H7A 109.9
C8 C7 H7B 109.9
C1 C7 H7B 109.9
H7A C7 H7B 108.3
C4 C8 C7 107.88(11)
C4 C8 H8A 110.1
C7 C8 H8A 110.1
C4 C8 H8B 110.1
C7 C8 H8B 110.1
H8A C8 H8B 108.4
C4 C9 H9A 109.5
C4 C9 H9B 109.5
H9A C9 H9B 109.5
C4 C9 H9C 109.5
H9A C9 H9C 109.5
H9B C9 H9C 109.5
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
C1 C2 1.5203(18)
C1 C6 1.5229(18)
C1 C7 1.5571(19)
C1 H1 1.0000
O2 C2 1.2324(16)
C2 N3 1.3414(17)
N3 C4 1.4697(16)
N3 H3 0.8800
C4 N5 1.4675(16)
C4 C9 1.5124(18)
C4 C8 1.5399(19)
N5 C6 1.3362(16)
N5 H5 0.8800
O6 C6 1.2408(16)
C7 C8 1.5464(19)
C7 H7A 0.9900
C7 H7B 0.9900
C8 H8A 0.9900
C8 H8B 0.9900
C9 H9A 0.9800
C9 H9B 0.9800
C9 H9C 0.9800
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
C6 C1 C2 O2 124.56(13)
C7 C1 C2 O2 -121.23(14)
C6 C1 C2 N3 -55.26(14)
C7 C1 C2 N3 58.95(14)
O2 C2 N3 C4 -178.24(12)
C1 C2 N3 C4 1.58(15)
C2 N3 C4 N5 52.09(14)
C2 N3 C4 C9 172.93(11)
C2 N3 C4 C8 -62.18(14)
N3 C4 N5 C6 -52.48(14)
C9 C4 N5 C6 -173.59(11)
C8 C4 N5 C6 61.79(14)
C4 N5 C6 O6 179.45(12)
C4 N5 C6 C1 -0.86(15)
C2 C1 C6 O6 -125.28(13)
C7 C1 C6 O6 120.54(14)
C2 C1 C6 N5 55.04(14)
C7 C1 C6 N5 -59.14(13)
C2 C1 C7 C8 -57.79(14)
C6 C1 C7 C8 56.72(13)
N5 C4 C8 C7 -57.75(13)
N3 C4 C8 C7 56.97(13)
C9 C4 C8 C7 179.89(11)
C1 C7 C8 C4 0.55(14)
