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###           Full Paper (Acta Crystallographica Section C)                ###
###                                                                        ###
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#                                                                            #
# This CIF contains the data in a paper accepted for publication in Acta     #
# Crystallographica Section C. It conforms to the editorial and technical    #
# requirements of Notes for Authors for Section C, and has been peer         #
# reviewed under the auspices of the IUCr Commission on Journals.            #
#                                                                            #
# Full details of the Crystallographic Information File format               #
# are given in the paper "The Crystallographic Information File (CIF):       #
# a New Standard Archive File for Crystallography" by S. R. Hall, F. H.      #
# Allen and I. D. Brown [Acta Cryst. (1991), A47, 655-685].                  #
#                                                                            #
# The current version of the core CIF dictionary is obtainable from          #
# ftp://ftp.iucr.org/pub/cif_core.dic. The current version number is 2.1.    #
#                                                                            #
# Software is freely available for graphical display of the structure(s) in  #
# this CIF.  For information consult the CIF home page http://www.iucr.org/  #
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data_global
_audit_creation_method     SHELXL-97
_journal_date_recd_electronic     2005-05-03
_journal_date_accepted     2005-06-30
_journal_name_full     'Acta Crystallographica, Section C'
_journal_year     2005
_journal_volume     61
_journal_issue      8
_journal_page_first     o512
_journal_page_last     o514
_journal_paper_category     FO
_journal_coeditor_code     HJ1060
_publ_contact_author_name     'Dr Maciej Kubicki'
_publ_contact_author_address
;
Faculty of Chemistry
Adam Mickiewicz University
Grunwaldzka 6
60-780 Poznań, Poland
;
_publ_contact_author_email     mkubicki@amu.edu.pl
_publ_section_title
;
2,2'-Dimethyl-4,5'-dinitro-1H,3'H-1,4'-biimidazole monohydrate
;
loop_
    _publ_author_name
    _publ_author_address
    'Kubicki, Maciej'
;
Department of Chemistry
Adam Mickiewicz University
Grunwaldzka 6
60-780 Poznań
Poland
;
data_I
_audit_creation_method     SHELXL-97
_chemical_name_systematic
;
2,2'-Dimethyl-4,5'-dinitro-1H,3'H-1,4'-biimidazole monohydrate
;
_chemical_name_common     ?
_chemical_formula_moiety     'C8 H8 N6 O4, H2 O'
_chemical_formula_sum     'C8 H10 N6 O5'
_chemical_formula_iupac     'C8 H8 N6 O4, H2 O'
_chemical_formula_weight     270.22
_chemical_melting_point     ?
_symmetry_cell_setting     monoclinic
_symmetry_space_group_name_H-M     'P 21'
_symmetry_space_group_name_Hall     'P 2yb'
loop_
    _symmetry_equiv_pos_as_xyz
    'x, y, z'
    '-x, y+1/2, -z'
_cell_length_a     6.5951(8)
_cell_length_b     13.4920(13)
_cell_length_c     7.2032(9)
_cell_angle_alpha     90.00
_cell_angle_beta     113.084(12)
_cell_angle_gamma     90.00
_cell_volume     589.63(13)
_cell_formula_units_Z     2
_cell_measurement_reflns_used     2200
_cell_measurement_theta_min     3
_cell_measurement_theta_max     20
_cell_measurement_temperature     100.0(10)
_exptl_crystal_description     prism
_exptl_crystal_colour     colourless
_exptl_crystal_size_max     0.15
_exptl_crystal_size_mid     0.1
_exptl_crystal_size_min     0.1
_exptl_crystal_density_diffrn     1.522
_exptl_crystal_density_meas     .
_exptl_crystal_density_method     'not measured'
_exptl_crystal_F_000     280
_exptl_absorpt_coefficient_mu     0.128
_exptl_absorpt_correction_type     'multi-scan'
_exptl_absorpt_process_details     '(SORTAV; Blessing, 1995, 1997)'
_exptl_absorpt_correction_T_min     0.9887
_exptl_absorpt_correction_T_max     0.9890
_exptl_special_details
;
;
_diffrn_ambient_temperature     100.0(10)
_diffrn_radiation_type     MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_source     'fine-focus sealed tube'
_diffrn_radiation_monochromator     graphite
_diffrn_measurement_device_type     'Kuma KM-4 CCD four-circle'
_diffrn_measurement_method     ω
_diffrn_reflns_number     5482
_diffrn_reflns_av_R_equivalents     0.039
_diffrn_reflns_av_sigmaI/netI     0.0948
_diffrn_reflns_theta_min     3.86
_diffrn_reflns_theta_max     29.78
_diffrn_reflns_theta_full     25.00
_diffrn_measured_fraction_theta_max     0.911
_diffrn_measured_fraction_theta_full     0.994
_diffrn_reflns_limit_h_min     -9
_diffrn_reflns_limit_h_max     8
_diffrn_reflns_limit_k_min     -18
_diffrn_reflns_limit_k_max     18
_diffrn_reflns_limit_l_min     -8
_diffrn_reflns_limit_l_max     9
_refine_special_details
;
 Refinement of F² against ALL reflections.  The weighted R-factor wR and
 goodness of fit S are based on F², conventional R-factors R are based
 on F, with F set to zero for negative F². The threshold expression of
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is
 not relevant to the choice of reflections for refinement.  R-factors based
 on F² are statistically about twice as large as those based on F, and R-
 factors based on ALL data will be even larger.
;
_reflns_number_total     1595
_reflns_number_gt     1060
_reflns_threshold_expression     I>2σ(I)
_refine_ls_structure_factor_coef     Fsqd
_refine_ls_matrix_type     full
_refine_ls_R_factor_all     0.0617
_refine_ls_R_factor_gt     0.0345
_refine_ls_wR_factor_gt     0.0450
_refine_ls_wR_factor_ref     0.0492
_refine_ls_goodness_of_fit_ref     0.835
_refine_ls_restrained_S_all     0.835
_refine_ls_number_reflns     1598
_refine_ls_number_parameters     192
_refine_ls_number_restraints     1
_refine_ls_hydrogen_treatment     mixed
_refine_ls_weighting_scheme     calc
_refine_ls_weighting_details
                   'calc w=1/[σ²(Fo²)+(0.01P)²] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_hydrogens     geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary     difmap
_refine_ls_shift/su_max     0.002
_refine_ls_shift/su_mean     0.000
_refine_diff_density_max     0.209
_refine_diff_density_min     -0.219
_refine_ls_extinction_method     SHELXL97
_refine_ls_extinction_coef     0.026(2)
_refine_ls_extinction_expression
                                  'Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^'
_refine_ls_abs_structure_Flack     .
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'
_computing_data_collection     'CrysAlis CCD  (Oxford Diffraction, 2002)'
_computing_cell_refinement     'CrysAlis CCD'
_computing_data_reduction     'CrysAlis RED (Oxford Diffraction, 2002)'
_computing_structure_solution     'SHELXS97 (Sheldrick, 1990)'
_computing_structure_refinement     'SHELXL97 (Sheldrick, 1997)'
_computing_molecular_graphics     'program (reference)?'
_computing_publication_material     'program (reference)?'
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
    C2 0.6422(4) 0.42840(18) 0.3674(4) 0.0196(6) Uani d . 1 . . C
    C2' 0.3758(4) 0.68804(19) -0.0050(4) 0.0179(6) Uani d . 1 . . C
    C21 0.4027(4) 0.40469(19) 0.2704(4) 0.0230(7) Uani d . 1 . . C
    C21' 0.1941(5) 0.7611(2) -0.0462(4) 0.0277(7) Uani d . 1 . . C
    C4 0.9873(4) 0.42481(19) 0.5458(4) 0.0163(6) Uani d . 1 . . C
    C4' 0.6283(4) 0.57824(18) 0.1624(4) 0.0178(6) Uani d . 1 . . C
    C5 0.9611(4) 0.5072(2) 0.4311(4) 0.0187(6) Uani d . 1 . . C
    C5' 0.6347(4) 0.59922(19) -0.0196(4) 0.0173(6) Uani d . 1 . . C
    N1 0.7386(3) 0.50957(16) 0.3148(3) 0.0168(5) Uani d . 1 . . N
    N1' 0.4785(3) 0.66724(16) -0.1256(3) 0.0196(5) Uani d . 1 . . N
    N3 0.7926(3) 0.37558(14) 0.5079(3) 0.0193(5) Uani d . 1 . . N
    N3' 0.4613(4) 0.63594(16) 0.1703(3) 0.0183(5) Uani d . 1 . . N
    N4 1.1900(4) 0.38726(18) 0.6932(3) 0.0251(6) Uani d . 1 . . N
    N5' 0.7775(4) 0.55884(16) -0.1091(4) 0.0225(5) Uani d . 1 . . N
    O1W 0.2974(3) 0.67645(14) 0.4462(3) 0.0204(4) Uani d . 1 . . O
    O41 1.1832(3) 0.30927(14) 0.7794(3) 0.0323(5) Uani d . 1 . . O
    O42 1.3590(3) 0.43515(13) 0.7227(3) 0.0311(5) Uani d . 1 . . O
    O51' 0.7456(3) 0.58377(14) -0.2823(3) 0.0302(5) Uani d . 1 . . O
    O52' 0.9230(3) 0.50088(13) -0.0061(3) 0.0283(5) Uani d . 1 . . O
    H1W 0.235(6) 0.744(3) 0.426(5) 0.068(9) Uiso d . 1 . . H
    H21A 0.3760 0.3392 0.3153 0.051(6) Uiso calc R 1 . . H
    H21B 0.3561 0.4045 0.1234 0.051(6) Uiso calc R 1 . . H
    H21C 0.3186 0.4547 0.3087 0.051(6) Uiso calc R 1 . . H
    H21D 0.0947 0.7385 0.0166 0.062(6) Uiso calc R 1 . . H
    H21E 0.1119 0.7672 -0.1923 0.062(6) Uiso calc R 1 . . H
    H21F 0.2562 0.8257 0.0099 0.062(6) Uiso calc R 1 . . H
    H2W 0.371(6) 0.676(3) 0.582(5) 0.068(9) Uiso d . 1 . . H
    H3' 0.418(4) 0.6461(18) 0.264(4) 0.019(8) Uiso d . 1 . . H
    H5 1.058(4) 0.5590(19) 0.426(4) 0.025(8) Uiso d . 1 . . H
loop_
    _atom_site_aniso_label
    _atom_site_aniso_U_11
    _atom_site_aniso_U_22
    _atom_site_aniso_U_33
    _atom_site_aniso_U_12
    _atom_site_aniso_U_13
    _atom_site_aniso_U_23
    C2 0.0228(14) 0.0185(15) 0.0181(14) 0.0026(12) 0.0086(12) 0.0001(12)
    C2' 0.0185(14) 0.0175(15) 0.0175(15) 0.0018(12) 0.0070(12) -0.0003(12)
    C21 0.0176(14) 0.0236(17) 0.0261(16) 0.0000(12) 0.0067(12) 0.0026(13)
    C21' 0.0259(16) 0.0288(17) 0.0286(18) 0.0073(14) 0.0107(15) 0.0062(14)
    C4 0.0145(13) 0.0165(14) 0.0151(14) 0.0009(12) 0.0030(11) -0.0013(12)
    C4' 0.0159(13) 0.0175(15) 0.0177(15) 0.0017(12) 0.0042(11) -0.0017(12)
    C5 0.0189(14) 0.0214(15) 0.0157(14) -0.0030(13) 0.0067(12) -0.0012(13)
    C5' 0.0182(13) 0.0173(15) 0.0178(15) 0.0016(11) 0.0086(12) -0.0010(12)
    N1 0.0177(11) 0.0173(12) 0.0148(12) 0.0003(11) 0.0056(9) 0.0007(10)
    N1' 0.0221(12) 0.0184(12) 0.0182(13) 0.0010(10) 0.0079(10) -0.0004(10)
    N3 0.0195(11) 0.0192(13) 0.0166(12) 0.0017(10) 0.0044(10) -0.0006(10)
    N3' 0.0209(12) 0.0203(12) 0.0158(13) 0.0021(10) 0.0093(11) 0.0009(10)
    N4 0.0269(15) 0.0268(14) 0.0192(13) 0.0025(12) 0.0064(11) -0.0028(12)
    N5' 0.0210(13) 0.0254(14) 0.0207(13) 0.0002(11) 0.0077(11) -0.0021(11)
    O1W 0.0262(10) 0.0186(11) 0.0160(11) 0.0030(10) 0.0077(9) -0.0007(9)
    O41 0.0306(12) 0.0281(12) 0.0324(12) 0.0038(10) 0.0061(10) 0.0118(10)
    O42 0.0171(10) 0.0353(12) 0.0337(12) -0.0037(9) 0.0023(9) 0.0001(10)
    O51' 0.0384(12) 0.0361(12) 0.0199(12) 0.0089(10) 0.0156(9) 0.0056(10)
    O52' 0.0256(11) 0.0292(13) 0.0283(12) 0.0110(10) 0.0087(9) 0.0039(10)
_geom_special_details
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
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
    N1 C5 . 1.376(3) y
    N1 C2 . 1.391(3) y
    N1 C4' . 1.402(3) y
    C2 N3 . 1.315(3) y
    C2 C21 . 1.490(3) ?
    C21 H21A . 0.9800 ?
    C21 H21B . 0.9800 ?
    C21 H21C . 0.9800 ?
    N3 C4 . 1.375(3) y
    C4 C5 . 1.354(4) ?
    C4 N4 . 1.434(3) ?
    N4 O41 . 1.231(3) ?
    N4 O42 . 1.233(3) ?
    C5 H5 . 0.96(2) ?
    N1' C2' . 1.325(3) y
    N1' C5' . 1.367(3) y
    C2' N3' . 1.359(3) y
    C2' C21' . 1.489(4) ?
    C21' H21D . 0.9800 ?
    C21' H21E . 0.9800 ?
    C21' H21F . 0.9800 ?
    N3' C4' . 1.368(3) y
    N3' H3' . 0.84(2) ?
    C5' C4' . 1.358(3) ?
    C5' N5' . 1.440(3) ?
    N5' O51' . 1.228(2) ?
    N5' O52' . 1.235(3) ?
    O1W H1W . 0.99(4) ?
    O1W H2W . 0.91(4) ?
loop_
    _geom_angle_atom_site_label_1
    _geom_angle_atom_site_label_2
    _geom_angle_atom_site_label_3
    _geom_angle_site_symmetry_1
    _geom_angle_site_symmetry_3
    _geom_angle
    _geom_angle_publ_flag
    C5 N1 C2 . . 107.9(2) y
    C5 N1 C4' . . 126.5(2) y
    C2 N1 C4' . . 125.5(2) y
    N3 C2 N1 . . 110.4(2) y
    N3 C2 C21 . . 125.9(2) ?
    N1 C2 C21 . . 123.7(2) ?
    C2 C21 H21A . . 109.5 ?
    C2 C21 H21B . . 109.5 ?
    H21A C21 H21B . . 109.5 ?
    C2 C21 H21C . . 109.5 ?
    H21A C21 H21C . . 109.5 ?
    H21B C21 H21C . . 109.5 ?
    C2 N3 C4 . . 104.8(2) ?
    C5 C4 N3 . . 112.9(2) ?
    C5 C4 N4 . . 126.9(2) ?
    N3 C4 N4 . . 120.2(2) ?
    O41 N4 O42 . . 124.7(2) y
    O41 N4 C4 . . 117.9(2) y
    O42 N4 C4 . . 117.4(2) y
    C4 C5 N1 . . 104.0(2) ?
    C4 C5 H5 . . 134.0(15) ?
    N1 C5 H5 . . 121.9(15) ?
    C2' N1' C5' . . 104.1(2) y
    N1' C2' N3' . . 111.5(2) ?
    N1' C2' C21' . . 126.0(2) ?
    N3' C2' C21' . . 122.4(2) ?
    C2' C21' H21D . . 109.5 ?
    C2' C21' H21E . . 109.5 ?
    H21D C21' H21E . . 109.5 ?
    C2' C21' H21F . . 109.5 ?
    H21D C21' H21F . . 109.5 ?
    H21E C21' H21F . . 109.5 ?
    C2' N3' C4' . . 107.7(2) y
    C2' N3' H3' . . 121.0(17) ?
    C4' N3' H3' . . 131.1(17) ?
    C4' C5' N1' . . 112.2(2) ?
    C4' C5' N5' . . 128.8(2) ?
    N1' C5' N5' . . 119.1(2) ?
    C5' C4' N3' . . 104.6(2) ?
    C5' C4' N1 . . 133.7(2) ?
    N3' C4' N1 . . 121.5(2) y
    O51' N5' O52' . . 124.5(2) y
    O51' N5' C5' . . 118.0(2) y
    O52' N5' C5' . . 117.5(2) y
    H1W O1W H2W . . 100(3) ?
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_site_symmetry_1
    _geom_torsion_site_symmetry_2
    _geom_torsion_site_symmetry_3
    _geom_torsion_site_symmetry_4
    _geom_torsion
    _geom_torsion_publ_flag
    C5 N1 C2 N3 . . . . -0.6(3) ?
    C4' N1 C2 N3 . . . . 176.3(2) ?
    C5 N1 C2 C21 . . . . -178.7(2) ?
    C4' N1 C2 C21 . . . . -1.8(3) ?
    N1 C2 N3 C4 . . . . 0.5(3) ?
    C21 C2 N3 C4 . . . . 178.5(2) ?
    C2 N3 C4 C5 . . . . -0.2(3) ?
    C2 N3 C4 N4 . . . . -179.8(2) ?
    C5 C4 N4 O41 . . . . -177.9(2) ?
    N3 C4 N4 O41 . . . . 1.7(3) ?
    C5 C4 N4 O42 . . . . 1.3(3) ?
    N3 C4 N4 O42 . . . . -179.1(2) ?
    N3 C4 C5 N1 . . . . -0.2(3) ?
    N4 C4 C5 N1 . . . . 179.4(2) ?
    C2 N1 C5 C4 . . . . 0.5(3) ?
    C4' N1 C5 C4 . . . . -176.4(2) ?
    C5' N1' C2' N3' . . . . 0.0(3) ?
    C5' N1' C2' C21' . . . . 178.0(2) ?
    N1' C2' N3' C4' . . . . -0.1(3) ?
    C21' C2' N3' C4' . . . . -178.2(2) ?
    C2' N1' C5' C4' . . . . 0.1(3) ?
    C2' N1' C5' N5' . . . . 179.3(2) ?
    N1' C5' C4' N3' . . . . -0.2(3) ?
    N5' C5' C4' N3' . . . . -179.2(2) ?
    N1' C5' C4' N1 . . . . 173.9(3) ?
    N5' C5' C4' N1 . . . . -5.1(5) ?
    C2' N3' C4' C5' . . . . 0.1(3) ?
    C2' N3' C4' N1 . . . . -174.9(2) ?
    C5 N1 C4' C5' . . . . 64.9(4) ?
    C2 N1 C4' C5' . . . . -111.5(3) ?
    C5 N1 C4' N3' . . . . -121.8(3) ?
    C2 N1 C4' N3' . . . . 61.8(3) ?
    C4' C5' N5' O51' . . . . 175.4(3) ?
    N1' C5' N5' O51' . . . . -3.5(3) ?
    C4' C5' N5' O52' . . . . -4.1(4) ?
    N1' C5' N5' O52' . . . . 176.9(2) ?
loop_
    _geom_hbond_atom_site_label_D
    _geom_hbond_atom_site_label_H
    _geom_hbond_atom_site_label_A
    _geom_hbond_site_symmetry_A
    _geom_hbond_distance_DH
    _geom_hbond_distance_HA
    _geom_hbond_distance_DA
    _geom_hbond_angle_DHA
    C21 H21B O41 1_454 0.98 2.62 3.499(3) 149
    C5 H5 O1W 1_655 0.96(2) 2.20(3) 3.155(3) 175(2)
    N3' H3' O1W . 0.84(2) 1.83(2) 2.665(3) 173(2)
    C21' H21F O52' 2_655 0.98 2.64 3.381(3) 133
    O1W H1W N3 2_656 0.99(4) 1.86(3) 2.799(3) 157(3)
    O1W H2W N1' 1_556 0.91(4) 1.94(4) 2.840(3) 170(3)
