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#$Date: 2016-02-20 00:18:51 +0200 (Sat, 20 Feb 2016) $
#$Revision: 176760 $
#$URL: svn://www.crystallography.net/cod/cif/2/01/03/2010324.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_2010324
loop_
_publ_author_name
'Dekaprilevich, Marina O.'
'Suvorova, Lyudmila I.'
'Khmelnitskii, Lenor I.'
'Struchkov, Yuri T.'
_publ_contact_author
;
Dr. Marina O. Dekaprilevich
Institute of Organic Chemistry
47 Leninsky prosp.,
Moscow 117913
Russia
;
_publ_section_title
;1,6-Dimethyltetrahydroimidazo[4,5-d]-imidazole-2,5(1H,6H)-dione
 monohydrate
;
_journal_issue                   12
_journal_name_full               'Acta Crystallographica Section C'
_journal_page_first              2056
_journal_page_last               2058
_journal_paper_doi               10.1107/S0108270194004555
_journal_volume                  50
_journal_year                    1994
_chemical_formula_moiety         'C6 H10 N4 O2,H2 O'
_chemical_formula_sum            'C6 H12 N4 O3'
_chemical_formula_weight         188.20
_chemical_name_systematic
;
1,6-Dimethyltetrahydroimidazo[4,5-d]imidazole-2,5(1H,6H)-dione monohydrate
;
_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'
_audit_creation_method           SHELXL
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   5.5080(10)
_cell_length_b                   10.828(2)
_cell_length_c                   14.363(3)
_cell_measurement_reflns_used    24
_cell_measurement_temperature    153(2)
_cell_measurement_theta_max      12
_cell_measurement_theta_min      11.5
_cell_volume                     856.6(3)
_computing_structure_refinement  'SHELXL93 (Sheldrick, 1993)'
_computing_structure_solution    'SHELXTL-Plus (Sheldrick, 1987)'
_diffrn_ambient_temperature      153(2)
_diffrn_measurement_device       'Siemens P3/PC'
_diffrn_measurement_method       θ/2θ
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71069
_diffrn_reflns_av_R_equivalents  0.1347
_diffrn_reflns_av_sigmaI/netI    0.0281
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -2
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       -4
_diffrn_reflns_number            1845
_diffrn_reflns_theta_max         30.06
_diffrn_reflns_theta_min         2.36
_diffrn_standards_decay_%        1
_diffrn_standards_interval_count 98
_diffrn_standards_number         2
_exptl_absorpt_coefficient_mu    0.120
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.459
_exptl_crystal_description       needle
_exptl_crystal_F_000             400
_exptl_crystal_size_max          0.5
_exptl_crystal_size_mid          0.1
_exptl_crystal_size_min          0.1
_refine_diff_density_max         0.606
_refine_diff_density_min         -0.260
_refine_ls_abs_structure_details
;
refinement according to Flack (1983)
yielded unconclusive results due to the lack of strong enough anomalous
scatterers
;
_refine_ls_abs_structure_Flack   -1.(2)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_all   1.080
_refine_ls_goodness_of_fit_obs   1.087
_refine_ls_hydrogen_treatment    refall
_refine_ls_matrix_type           full
_refine_ls_number_parameters     158
_refine_ls_number_reflns         1746
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.086
_refine_ls_restrained_S_obs      1.087
_refine_ls_R_factor_all          0.0755
_refine_ls_R_factor_obs          0.0563
_refine_ls_shift/esd_max         0.004
_refine_ls_shift/esd_mean        0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_scheme
; calc w=1/[\s^2^(F~o~^2^)+(0.1131P)^2^ +0.0965P] where
P=(F~o~^2^ + 2F~c~^2^)/3
;
_refine_ls_wR_factor_all         0.1675
_refine_ls_wR_factor_obs         0.1503
_reflns_number_observed          1427
_reflns_number_total             1751
_reflns_observed_criterion       >2\s(I)
_cod_data_source_file            na1080.cif
_cod_data_source_block           gela2
_cod_database_code               2010324
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'-x, y+1/2, -z+1/2'
'x+1/2, -y+1/2, -z'
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
_atom_site_refinement_flags
_atom_site_occupancy
_atom_site_disorder_group
_atom_site_type_symbol
C(1) 0.1737(4) 0.7740(3) 0.22501(14) 0.0260(4) Uani d . 1 . C
N(2) 0.3005(4) 0.6605(2) 0.2426(2) 0.0324(5) Uani d . 1 . N
C(3) 0.2055(4) 0.5950(2) 0.3148(2) 0.0245(5) Uani d . 1 . C
N(4) 0.0195(4) 0.6612(2) 0.35282(15) 0.0286(4) Uani d . 1 . N
C(5) -0.0284(3) 0.7733(3) 0.30110(14) 0.0242(4) Uani d . 1 . C
N(6) 0.0160(4) 0.8859(2) 0.3521(2) 0.0293(5) Uani d . 1 . N
C(7) 0.2074(4) 0.9502(2) 0.3173(2) 0.0256(5) Uani d . 1 . C
N(8) 0.3093(4) 0.8848(2) 0.24709(15) 0.0305(5) Uani d . 1 . N
C(9) -0.1483(5) 0.6094(3) 0.4193(2) 0.0311(6) Uani d . 1 . C
C(10) -0.1487(5) 0.9343(3) 0.4213(2) 0.0319(6) Uani d . 1 . C
O(11) 0.2733(3) 0.4921(2) 0.34124(13) 0.0316(4) Uani d . 1 . O
O(12) 0.2778(3) 1.0523(2) 0.34529(14) 0.0334(4) Uani d . 1 . O
O(1W) 0.2632(8) 0.7981(3) 0.0018(2) 0.097(2) Uani d . 1 . O
H(1W) 0.1648(8) 0.7183(3) -0.0299(2) 0.050 Uiso d R 1 . H
H(2W) 0.2488(8) 0.8507(3) -0.0510(2) 0.050 Uiso d R 1 . H
H(1) 0.115(6) 0.771(3) 0.162(2) 0.034(8) Uiso d . 1 . H
H(2) 0.393(9) 0.629(3) 0.213(3) 0.049(11) Uiso d . 1 . H
H(5) -0.183(6) 0.769(3) 0.285(2) 0.028(7) Uiso d . 1 . H
H(8) 0.439(6) 0.915(3) 0.214(2) 0.023(7) Uiso d . 1 . H
H(91) -0.146(6) 0.660(3) 0.480(2) 0.026(7) Uiso d . 1 . H
H(92) -0.086(8) 0.533(3) 0.432(2) 0.040(10) Uiso d . 1 . H
H(93) -0.339(7) 0.616(3) 0.393(2) 0.037(9) Uiso d . 1 . H
H(101) -0.106(10) 1.009(4) 0.433(3) 0.060(13) Uiso d . 1 . H
H(102) -0.152(11) 0.891(4) 0.474(4) 0.087(16) Uiso d . 1 . H
H(103) -0.305(9) 0.910(4) 0.388(3) 0.067(13) Uiso d . 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
N(2) C(1) N(8) 114.8(2) yes
N(2) C(1) C(5) 102.7(2) yes
N(8) C(1) C(5) 102.6(2) yes
N(2) C(1) H(1) 107.(2) ?
N(8) C(1) H(1) 114.(2) ?
C(5) C(1) H(1) 115.(2) ?
C(3) N(2) C(1) 113.1(2) yes
C(3) N(2) H(2) 117.(3) ?
C(1) N(2) H(2) 128.(3) ?
O(11) C(3) N(2) 126.0(2) yes
O(11) C(3) N(4) 125.3(2) yes
N(2) C(3) N(4) 108.6(2) yes
C(3) N(4) C(9) 122.8(2) yes
C(3) N(4) C(5) 111.9(2) yes
C(9) N(4) C(5) 123.3(2) yes
N(6) C(5) N(4) 114.6(2) yes
N(6) C(5) C(1) 103.4(2) yes
N(4) C(5) C(1) 103.5(2) yes
N(6) C(5) H(5) 110.(2) ?
N(4) C(5) H(5) 105.(2) ?
C(1) C(5) H(5) 120.(2) ?
C(7) N(6) C(5) 112.2(2) yes
C(7) N(6) C(10) 123.7(2) yes
C(5) N(6) C(10) 123.3(2) yes
O(12) C(7) N(8) 125.4(2) yes
O(12) C(7) N(6) 125.5(2) yes
N(8) C(7) N(6) 109.1(2) yes
C(7) N(8) C(1) 112.5(2) yes
C(7) N(8) H(8) 121.5(19) ?
C(1) N(8) H(8) 125.6(19) ?
N(4) C(9) H(91) 110.3(18) ?
N(4) C(9) H(92) 104.(2) ?
H(91) C(9) H(92) 108.(3) ?
N(4) C(9) H(93) 110.9(18) ?
H(91) C(9) H(93) 105.(3) ?
H(92) C(9) H(93) 118.(3) ?
N(6) C(10) H(101) 108.(3) ?
N(6) C(10) H(102) 114.(4) ?
H(101) C(10) H(102) 110.(4) ?
N(6) C(10) H(103) 96.(3) ?
H(101) C(10) H(103) 124.(4) ?
H(102) C(10) H(103) 104.(5) ?
H(1W) O(1W) H(2W) 95.6 ?
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
C(1) N(2) . 1.435(4) yes
C(1) N(8) . 1.449(3) yes
C(1) C(5) . 1.560(3) yes
C(1) H(1) . 0.97(3) ?
N(2) C(3) . 1.362(3) yes
N(2) H(2) . 0.75(4) ?
C(3) O(11) . 1.235(3) yes
C(3) N(4) . 1.364(3) yes
N(4) C(9) . 1.442(3) yes
N(4) C(5) . 1.448(3) yes
C(5) N(6) . 1.443(3) yes
C(5) H(5) . 0.88(3) ?
N(6) C(7) . 1.359(3) yes
N(6) C(10) . 1.445(3) yes
C(7) O(12) . 1.238(3) yes
C(7) N(8) . 1.355(3) yes
N(8) H(8) . 0.92(3) ?
C(9) H(91) . 1.03(3) ?
C(9) H(92) . 0.92(4) ?
C(9) H(93) . 1.12(4) ?
C(10) H(101) . 0.86(5) ?
C(10) H(102) . 0.88(6) ?
C(10) H(103) . 1.02(5) ?
O(1W) H(1W) . 1.12 ?
O(1W) H(2W) . 0.95 ?
