#------------------------------------------------------------------------------
#$Date: 2018-06-14 15:53:24 +0300 (Thu, 14 Jun 2018) $
#$Revision: 208377 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/00/65/2006546.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_2006546
loop_
_publ_author_name
'Piacenza, Guy'
'Beguet, Christelle'
'Wimmer, Eric'
'Gallo, Roger'
'Giorgi, Michel'
_publ_section_title
;
 2,4,6,8-Tetraazabicyclo[3.3.1]nonane-3,7-dione and
 2,4,6,8-Tetraacetyl-2,4,6,8-tetraazabicyclo[3.3.1]nonane-3,7-dione
;
_journal_issue                   10
_journal_name_full               'Acta Crystallographica Section C'
_journal_page_first              1459
_journal_page_last               1462
_journal_paper_doi               10.1107/S0108270197006495
_journal_volume                  53
_journal_year                    1997
_chemical_formula_sum            'C13 H16 N4 O6'
_chemical_formula_weight         324.30
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2ybc'
_space_group_name_H-M_alt        'P 1 21/c 1'
_atom_type_scat_source           IntTabIV
_cell_angle_alpha                90.00(2)
_cell_angle_beta                 99.63(2)
_cell_angle_gamma                90.00(2)
_cell_formula_units_Z            4
_cell_length_a                   8.979(2)
_cell_length_b                   16.265(6)
_cell_length_c                   10.3420(10)
_cell_measurement_reflns_used    25
_cell_measurement_temperature    294
_cell_measurement_theta_max      16
_cell_measurement_theta_min      12
_cell_volume                     1489.1(7)
_computing_cell_refinement       'CAD4 Software'
_computing_data_collection       'CAD4 Software (Enraf-Nonius, 1989)'
_computing_data_reduction        'BEGIN SDP (Frenz, 1985)'
_computing_molecular_graphics    'ORTEPII (Johnson, 1976)'
_computing_publication_material  'CIF VAX in MolEN (Fair, 1990)'
_computing_structure_refinement  'LSFM SDP (Frenz, 1985)'
_computing_structure_solution
'direct methods (MULTAN80; Main et al., 1980)'
_diffrn_ambient_temperature      294
_diffrn_measurement_device       Enraf_Nonius_CAD4
_diffrn_measurement_method       ω/2θ
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.024
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_k_min       0
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_limit_l_min       0
_diffrn_reflns_number            2570
_diffrn_reflns_theta_max         24
_diffrn_reflns_theta_min         2
_diffrn_standards_decay_%        0.32
_diffrn_standards_interval_time  60
_diffrn_standards_number         2
_exptl_absorpt_coefficient_mu    0.109
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.45
_exptl_crystal_density_method    none
_exptl_crystal_description       cubic
_exptl_crystal_F_000             680
_exptl_crystal_size_max          0.40
_exptl_crystal_size_mid          0.40
_exptl_crystal_size_min          0.40
_refine_diff_density_max         0.272
_refine_diff_density_min         -0.192
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_obs   2.165
_refine_ls_hydrogen_treatment    noref
_refine_ls_matrix_type           full
_refine_ls_number_parameters     208
_refine_ls_number_reflns         2058
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.071
_refine_ls_R_factor_obs          .047
_refine_ls_shift/esd_max         0.000
_refine_ls_structure_factor_coef F
_refine_ls_weighting_details     'w = 4Fo²/[σ²(Fo²) + 0.0016Fo⁴]'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_obs         .062
_reflns_number_observed          2058
_reflns_number_total             2321
_reflns_observed_criterion       >0.5\s(I)
_cod_data_source_file            ab1467.cif
_cod_data_source_block           II
_cod_depositor_comments
;
 Updating space group information and adding the symmetry operation list.

 Antanas Vaitkus,
 2018-06-15

The following automatic conversions were performed:

'_refine_ls_weighting_scheme' value '4Fo^2^/[\s^2^(Fo^2^) +
0.0016Fo^4^]' was changed to 'calc'. New tag
'_refine_ls_weighting_details' was created. The value of the new tag
was set to 'w = 4Fo^2^/[\s^2^(Fo^2^) + 0.0016Fo^4^]'.

Automatic conversion script
Id: cif_fix_values 3143 2015-03-26 13:38:13Z robertas 
;
_cod_original_cell_volume        1489.0(10)
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               2006546
_cod_database_fobs_code          2006546
loop_
_space_group_symop_id
_space_group_symop_operation_xyz
1 x,y,z
2 -x,y+1/2,-z+1/2
3 -x,-y,-z
4 x,-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_thermal_displace_type
_atom_site_calc_flag
N1 .4298(2) .13760(10) .94520(10) .0351(4) Uani ?
O1 .5021(2) .02210(10) .84610(10) .0496(4) Uani ?
N2 .2565(2) .03230(10) .8739(2) .0363(4) Uani ?
O2 -.0372(2) .05060(10) .7141(2) .0711(5) Uani ?
N3 .0881(2) .14790(10) .84070(10) .0342(4) Uani ?
C1 .1441(2) .07970(10) .9298(2) .0365(5) Uani ?
C2 .4027(2) .06090(10) .8835(2) .0353(5) Uani ?
O3 .3272(2) .32570(10) 1.1400(2) .0599(5) Uani ?
C3 .2185(2) -.05150(10) .8410(2) .0462(6) Uani ?
N4 .2483(2) .24320(10) .96660(10) .0366(4) Uani ?
O4 .1306(2) -.08590(10) .8980(2) .0638(5) Uani ?
C4 .5527(2) .18810(10) .9288(2) .0442(6) Uani ?
C5 .3305(2) .17290(10) 1.0321(2) .0363(5) Uani ?
O5 .0538(2) .28630(10) .8128(2) .0648(5) Uani ?
O6 .5688(2) .25130(10) .9907(2) .0688(5) Uani ?
C6 -.0088(2) .12310(10) .7257(2) .0456(6) Uani ?
C7 .2176(2) .11110(10) 1.0611(2) .0385(5) Uani ?
C8 .1257(2) .23030(10) .8680(2) .0389(5) Uani ?
C9 .2832(3) -.0911(2) .7340(3) .0706(8) Uani ?
C10 -.0702(3) .1832(2) .6203(2) .0593(7) Uani ?
C11 .2817(3) .32230(10) 1.0244(2) .0477(6) Uani ?
C12 .6553(3) .1658(2) .8350(2) .0569(7) Uani ?
C13 .2667(4) .3964(2) .9386(3) .0910(10) Uani ?
H71 .2687 .0643 1.1185 .0489 Uiso calc
H72 .1390 .1382 1.1095 .0489 Uiso calc
H51 .3974 .1896 1.1176 .0449 Uiso calc
H11 .0539 .0438 .9404 .0459 Uiso calc
H91 .2459 -.1501 .7218 .0915 Uiso calc
H92 .2499 -.0592 .6482 .0915 Uiso calc
H93 .3982 -.0905 .7557 .0915 Uiso calc
H101 -.1372 .1523 .5459 .0754 Uiso calc
H102 -.1324 .2262 .6580 .0754 Uiso calc
H103 .0168 .2102 .5849 .0754 Uiso calc
H131 .2936 .4475 .9946 .1084 Uiso calc
H132 .3368 .3909 .8719 .1084 Uiso calc
H133 .1573 .4010 .8914 .1084 Uiso calc
H121 .7375 .2089 .8361 .0707 Uiso calc
H122 .7048 .1098 .8608 .0707 Uiso calc
H123 .5947 .1611 .7421 .0707 Uiso calc
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_publ_flag
C2 N1 C4 122.9(2) no
C2 N1 C5 122.9(2) no
C4 N1 C5 114.2(2) no
C1 N2 C2 120.3(2) yes
C1 N2 C3 116.3(2) yes
C2 N2 C3 121.6(2) yes
C1 N3 C6 114.2(2) no
C1 N3 C8 123.20(10) no
C6 N3 C8 122.6(2) no
N2 C1 N3 109.6(2) yes
N2 C1 C7 108.00(10) yes
N3 C1 C7 111.3(2) no
N1 C2 O1 121.9(2) no
N1 C2 N2 115.0(2) yes
O1 C2 N2 123.0(2) yes
N2 C3 O4 118.5(2) yes
N2 C3 C9 118.9(2) yes
O4 C3 C9 122.5(2) yes
C5 N4 C8 120.0(2) no
C5 N4 C11 117.10(10) no
C8 N4 C11 121.9(2) no
N1 C4 O6 117.4(2) no
N1 C4 C12 121.2(2) no
O6 C4 C12 121.4(2) no
N1 C5 N4 109.2(2) no
N1 C5 C7 111.1(2) no
N4 C5 C7 108.2(2) no
O2 C6 N3 116.9(2) no
O2 C6 C10 121.3(2) no
N3 C6 C10 121.8(2) no
C1 C7 C5 105.0(2) yes
N3 C8 N4 115.4(2) no
N3 C8 O5 122.4(2) no
N4 C8 O5 122.1(2) no
O3 C11 N4 118.1(2) no
O3 C11 C13 122.6(2) no
N4 C11 C13 119.2(2) no
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_publ_flag
N1 C2 1.404(3) no
N1 C4 1.408(3) no
N1 C5 1.483(3) no
O1 C2 1.208(3) yes
N2 C1 1.464(3) yes
N2 C2 1.381(2) yes
N2 C3 1.432(3) yes
O2 C6 1.208(3) no
N3 C1 1.475(2) no
N3 C6 1.410(2) no
N3 C8 1.400(3) no
C1 C7 1.497(3) yes
O3 C11 1.199(3) no
C3 O4 1.200(3) yes
C3 C9 1.480(4) yes
N4 C5 1.465(2) no
N4 C8 1.385(2) no
N4 C11 1.429(3) no
C4 O6 1.206(3) no
C4 C12 1.491(3) no
C5 C7 1.492(3) no
O5 C8 1.204(3) no
C6 C10 1.499(3) no
C11 C13 1.490(4) no
