#------------------------------------------------------------------------------
#$Date: 2017-10-13 09:09:21 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201973 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/20/25/2202574.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_2202574
loop_
_publ_author_name
'Furneaux, Richard H.'
'Gainsford, Graeme J.'
'Mason, Jennifer M.'
'Tyler, Peter C.'
_publ_section_title
(1R,2R,3S,5R,6R,7S,9aR,10aR)-4a,8a-Diazaperhydroanthracene-1,2,3,5,6,7-hexaol
_journal_issue                   9
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o1370
_journal_page_last               o1371
_journal_paper_doi               10.1107/S1600536803018397
_journal_volume                  59
_journal_year                    2003
_chemical_formula_iupac          'C12 H22 N2 O6'
_chemical_formula_moiety         'C12 H22 N2 O6'
_chemical_formula_structural     '(C12 H22 N2 O6)'
_chemical_formula_sum            'C12 H22 N2 O6'
_chemical_formula_weight         290.32
_chemical_name_systematic
;
 ?
;
_space_group_IT_number           19
_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_Hall  'P 2ac 2ab'
_symmetry_space_group_name_H-M   'P 21 21 21'
_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                 90.00
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   6.702(2)
_cell_length_b                   13.099(5)
_cell_length_c                   14.893(3)
_cell_measurement_reflns_used    24
_cell_measurement_temperature    173(2)
_cell_measurement_theta_max      23.8
_cell_measurement_theta_min      4.8
_cell_volume                     1307.4(7)
_computing_cell_refinement       SHELXTL
_computing_data_collection       'SHELXTL (Siemens, 1983)'
_computing_data_reduction        SHELXTL
_computing_molecular_graphics
;
 ORTEP-3 for Windows (Farrugia, 1997)
;
_computing_publication_material
;
SHELXL97
;
_computing_structure_refinement  'SHELXL97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS86 (Sheldrick, 1990)'
_diffrn_ambient_temperature      173(2)
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type
;
 Siemens/Nicolet R3m 4-circle diffractometer
;
_diffrn_measurement_method       'ω scan'
_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  0.039
_diffrn_reflns_av_sigmaI/netI    0.063
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       0
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       0
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       0
_diffrn_reflns_number            1608
_diffrn_reflns_theta_full        25.9
_diffrn_reflns_theta_max         25.9
_diffrn_reflns_theta_min         2.1
_diffrn_standards_decay_%        0.0
_diffrn_standards_interval_count 97
_diffrn_standards_number         3
_exptl_absorpt_coefficient_mu    0.118
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.475
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       needle
_exptl_crystal_F_000             624
_exptl_crystal_size_max          0.42
_exptl_crystal_size_mid          0.30
_exptl_crystal_size_min          0.15
_refine_diff_density_max         0.23
_refine_diff_density_min         -0.24
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.976
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     187
_refine_ls_number_reflns         1504
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.976
_refine_ls_R_factor_all          0.066
_refine_ls_R_factor_gt           0.046
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         <0.001
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0441P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.087
_refine_ls_wR_factor_ref         0.094
_reflns_number_gt                1146
_reflns_number_total             1504
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            cv6223.cif
_cod_data_source_block           II
_cod_depositor_comments
;
The following automatic conversions were performed:
'_geom_bond_publ_flag' value 'Y' changed to 'y' according to
'/home/saulius/struct/CIF-dictionaries/cif_core.dic' dictionary named
'cif_core.dic' version 2.4.1 from 2010-06-29 (4 times).

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

The following automatic conversions were performed:

'_geom_bond_publ_flag' value 'Y' changed to 'y' according to
/home/saulius/struct/CIF-dictionaries/cif_core.dic dictionary named
'cif_core.dic' version 2.4.1 from 2010-06-29 (4
times).

'_geom_angle_publ_flag' value 'Y' changed to 'y' according
to /home/saulius/struct/CIF-dictionaries/cif_core.dic dictionary
named 'cif_core.dic' version 2.4.1 from 2010-06-29 (2 times).

Automatic conversion script
Id: cif_fix_values 1715 2011-07-08 13:25:40Z adriana 
;
_cod_original_cell_volume        1307.5(7)
_cod_database_code               2202574
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'x+1/2, -y+1/2, -z'
'-x, y+1/2, -z+1/2'
'-x+1/2, -y, 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 -0.2909(4) 0.54689(19) 0.40930(17) 0.0200(6) Uani d . 1 . . O
H1O -0.3155 0.5005 0.3720 0.024 Uiso calc R 1 . . H
O2 0.0882(4) 0.57543(17) 0.32248(15) 0.0171(6) Uani d . 1 . . O
H2O 0.1564 0.6215 0.2980 0.021 Uiso calc R 1 . . H
O3 0.3816(4) 0.67349(18) 0.43697(18) 0.0210(6) Uani d . 1 . . O
H3O 0.4911 0.6466 0.4232 0.025 Uiso calc R 1 . . H
O5 0.2547(4) 0.26556(17) 0.72251(17) 0.0172(6) Uani d . 1 . . O
H5O 0.3275 0.2139 0.7158 0.021 Uiso calc R 1 . . H
O6 0.0154(4) 0.08534(18) 0.71468(16) 0.0171(6) Uani d . 1 . . O
H6O 0.0145 0.0671 0.7687 0.021 Uiso calc R 1 . . H
O7 -0.4163(4) 0.13234(17) 0.70110(18) 0.0188(6) Uani d . 1 . . O
H7O -0.3906 0.0696 0.7028 0.023 Uiso calc R 1 . . H
N4A 0.0594(4) 0.5401(2) 0.6052(2) 0.0136(7) Uani d . 1 . . N
N8A -0.1842(4) 0.3606(2) 0.5991(2) 0.0149(7) Uani d . 1 . . N
C1 -0.1007(5) 0.5273(3) 0.4517(2) 0.0143(8) Uani d . 1 . . C
H1 -0.0582 0.4555 0.4394 0.017 Uiso calc R 1 . . H
C2 0.0541(5) 0.6012(3) 0.4148(2) 0.0134(8) Uani d . 1 . . C
H2 -0.0005 0.6721 0.4181 0.016 Uiso calc R 1 . . H
C3 0.2473(6) 0.5964(3) 0.4683(2) 0.0150(8) Uani d . 1 . . C
H3 0.3099 0.5278 0.4603 0.018 Uiso calc R 1 . . H
C4 0.2039(6) 0.6142(2) 0.5678(2) 0.0159(8) Uani d . 1 . . C
H4A 0.3303 0.6094 0.6020 0.019 Uiso calc R 1 . . H
H4B 0.1506 0.6841 0.5758 0.019 Uiso calc R 1 . . H
C5 0.0836(5) 0.2572(2) 0.6656(2) 0.0129(8) Uani d . 1 . . C
H5 0.1248 0.2305 0.6055 0.016 Uiso calc R 1 . . H
C6 -0.0675(5) 0.1857(2) 0.7072(2) 0.0148(8) Uani d . 1 . . C
H6 -0.0980 0.2109 0.7691 0.018 Uiso calc R 1 . . H
C7 -0.2591(5) 0.1850(3) 0.6542(2) 0.0149(8) Uani d . 1 . . C
H7 -0.2360 0.1518 0.5946 0.018 Uiso calc R 1 . . H
C8 -0.3350(5) 0.2933(3) 0.6401(3) 0.0153(8) Uani d . 1 . . C
H8A -0.4544 0.2913 0.6010 0.018 Uiso calc R 1 . . H
H8B -0.3757 0.3221 0.6988 0.018 Uiso calc R 1 . . H
C9 0.1461(5) 0.4365(2) 0.6120(2) 0.0145(8) Uani d . 1 . . C
H9A 0.2693 0.4389 0.6487 0.017 Uiso calc R 1 . . H
H9B 0.1817 0.4114 0.5514 0.017 Uiso calc R 1 . . H
C9A -0.0033(5) 0.3642(3) 0.6551(2) 0.0130(8) Uani d . 1 . . C
H9 -0.0396 0.3910 0.7158 0.016 Uiso calc R 1 . . H
C10 -0.2718(5) 0.4641(3) 0.5941(2) 0.0164(8) Uani d . 1 . . C
H10A -0.3102 0.4862 0.6553 0.020 Uiso calc R 1 . . H
H10B -0.3946 0.4614 0.5572 0.020 Uiso calc R 1 . . H
C10A -0.1298(5) 0.5425(3) 0.5540(2) 0.0137(8) Uani d . 1 . . C
H10 -0.1909 0.6114 0.5630 0.016 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'
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
_geom_angle_publ_flag
C1 O1 H1O 109.5 ?
C2 O2 H2O 109.5 ?
C3 O3 H3O 109.5 ?
C5 O5 H5O 109.5 ?
C6 O6 H6O 109.5 ?
C7 O7 H7O 109.5 ?
C4 N4A C9 111.7(3) ?
C4 N4A C10A 110.7(3) ?
C9 N4A C10A 113.0(3) y
C9A N8A C8 110.5(3) ?
C9A N8A C10 109.0(3) ?
C8 N8A C10 107.3(3) y
O1 C1 C2 109.3(3) ?
O1 C1 C10A 107.2(3) ?
C2 C1 C10A 111.1(3) ?
O1 C1 H1 109.7 ?
C2 C1 H1 109.7 ?
C10A C1 H1 109.7 ?
O2 C2 C1 107.8(3) ?
O2 C2 C3 110.9(3) ?
C1 C2 C3 111.4(3) ?
O2 C2 H2 108.9 ?
C1 C2 H2 108.9 ?
C3 C2 H2 108.9 ?
O3 C3 C2 109.6(3) ?
O3 C3 C4 109.2(3) ?
C2 C3 C4 109.9(3) ?
O3 C3 H3 109.4 ?
C2 C3 H3 109.4 ?
C4 C3 H3 109.4 ?
N4A C4 C3 112.9(3) ?
N4A C4 H4A 109.0 ?
C3 C4 H4A 109.0 ?
N4A C4 H4B 109.0 ?
C3 C4 H4B 109.0 ?
H4A C4 H4B 107.8 ?
O5 C5 C6 110.0(3) ?
O5 C5 C9A 107.3(3) ?
C6 C5 C9A 110.8(3) ?
O5 C5 H5 109.6 ?
C6 C5 H5 109.6 ?
C9A C5 H5 109.6 ?
O6 C6 C7 111.4(3) ?
O6 C6 C5 109.9(3) ?
C7 C6 C5 111.1(3) ?
O6 C6 H6 108.1 ?
C7 C6 H6 108.1 ?
C5 C6 H6 108.1 ?
O7 C7 C6 111.8(3) ?
O7 C7 C8 105.6(3) ?
C6 C7 C8 110.5(3) ?
O7 C7 H7 109.6 ?
C6 C7 H7 109.6 ?
C8 C7 H7 109.6 ?
N8A C8 C7 112.7(3) ?
N8A C8 H8A 109.1 ?
C7 C8 H8A 109.1 ?
N8A C8 H8B 109.1 ?
C7 C8 H8B 109.1 ?
H8A C8 H8B 107.8 ?
N4A C9 C9A 110.0(3) ?
N4A C9 H9A 109.7 ?
C9A C9 H9A 109.7 ?
N4A C9 H9B 109.7 ?
C9A C9 H9B 109.7 ?
H9A C9 H9B 108.2 ?
N8A C9A C9 108.9(3) ?
N8A C9A C5 110.1(3) ?
C9 C9A C5 111.3(3) ?
N8A C9A H9 108.8 ?
C9 C9A H9 108.8 ?
C5 C9A H9 108.8 ?
N8A C10 C10A 113.0(3) ?
N8A C10 H10A 109.0 ?
C10A C10 H10A 109.0 ?
N8A C10 H10B 109.0 ?
C10A C10 H10B 109.0 ?
H10A C10 H10B 107.8 ?
N4A C10A C10 108.6(3) ?
N4A C10A C1 113.3(3) ?
C10 C10A C1 112.2(3) ?
N4A C10A H10 107.5 ?
C10 C10A H10 107.5 ?
C1 C10A H10 107.5 ?
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 C1 . 1.446(4) ?
O1 H1O . 0.8400 ?
O2 C2 . 1.434(4) ?
O2 H2O . 0.8400 ?
O3 C3 . 1.431(4) ?
O3 H3O . 0.8400 ?
O5 C5 . 1.431(4) ?
O5 H5O . 0.8400 ?
O6 C6 . 1.432(4) ?
O6 H6O . 0.8400 ?
O7 C7 . 1.440(4) ?
O7 H7O . 0.8400 ?
N4A C4 . 1.480(4) y
N4A C9 . 1.480(4) y
N4A C10A . 1.480(4) y
N8A C9A . 1.472(4) y
N8A C8 . 1.473(4) ?
N8A C10 . 1.479(4) ?
C1 C2 . 1.522(5) ?
C1 C10A . 1.548(5) ?
C1 H1 . 1.0000 ?
C2 C3 . 1.522(5) ?
C2 H2 . 1.0000 ?
C3 C4 . 1.528(5) ?
C3 H3 . 1.0000 ?
C4 H4A . 0.9900 ?
C4 H4B . 0.9900 ?
C5 C6 . 1.512(5) ?
C5 C9A . 1.526(4) ?
C5 H5 . 1.0000 ?
C6 C7 . 1.508(5) ?
C6 H6 . 1.0000 ?
C7 C8 . 1.521(5) ?
C7 H7 . 1.0000 ?
C8 H8A . 0.9900 ?
C8 H8B . 0.9900 ?
C9 C9A . 1.520(5) ?
C9 H9A . 0.9900 ?
C9 H9B . 0.9900 ?
C9A H9 . 1.0000 ?
C10 C10A . 1.523(5) ?
C10 H10A . 0.9900 ?
C10 H10B . 0.9900 ?
C10A H10 . 1.0000 ?
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
O1 C1 C2 O2 -67.9(4)
C10A C1 C2 O2 174.0(3)
O1 C1 C2 C3 170.2(3)
C10A C1 C2 C3 52.1(4)
O2 C2 C3 O3 65.4(4)
C1 C2 C3 O3 -174.6(3)
O2 C2 C3 C4 -174.6(3)
C1 C2 C3 C4 -54.6(4)
C9 N4A C4 C3 70.0(4)
C10A N4A C4 C3 -56.8(4)
O3 C3 C4 N4A 177.7(3)
C2 C3 C4 N4A 57.5(4)
O5 C5 C6 O6 -62.9(4)
C9A C5 C6 O6 178.7(3)
O5 C5 C6 C7 173.4(3)
C9A C5 C6 C7 55.0(4)
O6 C6 C7 O7 67.6(4)
C5 C6 C7 O7 -169.5(3)
O6 C6 C7 C8 -175.1(3)
C5 C6 C7 C8 -52.2(4)
C9A N8A C8 C7 -58.0(4)
C10 N8A C8 C7 -176.7(3)
O7 C7 C8 N8A 175.3(3)
C6 C7 C8 N8A 54.1(4)
C4 N4A C9 C9A 177.1(3)
C10A N4A C9 C9A -57.3(4)
C8 N8A C9A C9 -178.4(3)
C10 N8A C9A C9 -60.8(3)
C8 N8A C9A C5 59.2(4)
C10 N8A C9A C5 176.9(3)
N4A C9 C9A N8A 60.1(4)
N4A C9 C9A C5 -178.4(3)
O5 C5 C9A N8A -178.4(3)
C6 C5 C9A N8A -58.3(4)
O5 C5 C9A C9 60.8(4)
C6 C5 C9A C9 -179.2(3)
C9A N8A C10 C10A 59.5(4)
C8 N8A C10 C10A 179.2(3)
C4 N4A C10A C10 179.2(3)
C9 N4A C10A C10 53.0(4)
C4 N4A C10A C1 53.7(4)
C9 N4A C10A C1 -72.4(4)
N8A C10 C10A N4A -54.2(4)
N8A C10 C10A C1 71.8(4)
O1 C1 C10A N4A -171.4(3)
C2 C1 C10A N4A -52.1(4)
O1 C1 C10A C10 65.1(4)
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 21174777
