##############################################################################
###                                                                        ###
###        Electronic paper (Acta Crystallographica Section E)             ###
###                                                                        ###
##############################################################################
#                                                                            #
# This CIF contains the data in a paper accepted for publication in Acta     #
# Crystallographica Section E. It conforms to the requirements of Notes      #
# for Authors for Section E, 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/  #
# cif/home.html                                                              #
#                                                                            #
#            Copyright International Union of Crystallography                #
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##############################################################################
                                             
data_I
_audit_creation_method     SHELXL97
_chemical_name_systematic
;
1-Methyl-N-(2-{[(1-methyl-4-nitro-1H-pyrrol-2-yl)carbonyl]amino}ethyl)-
4-nitro-1H-pyrrole-2-carboxamide dimethylformamide disolvate
;
_chemical_name_common     ?
_chemical_formula_moiety     'C14 H16 N6 O6 , 2C3 H7 N O'
_chemical_formula_sum     'C20 H30 N8 O8'
_chemical_formula_iupac     'C14 H16 N6 O6 , 2C3 H7 N O'
_chemical_formula_weight     510.52
_chemical_melting_point     ?
_symmetry_cell_setting     triclinic
_symmetry_space_group_name_H-M     'P -1'
_symmetry_space_group_name_Hall     '-P 1'
loop_
    _symmetry_equiv_pos_as_xyz
    'x, y, z'
    '-x, -y, -z'
_cell_length_a     6.898(4)
_cell_length_b     8.904(6)
_cell_length_c     11.139(7)
_cell_angle_alpha     76.577(8)
_cell_angle_beta     89.075(8)
_cell_angle_gamma     71.959(7)
_cell_volume     631.6(7)
_cell_formula_units_Z     1
_cell_measurement_reflns_used     1169
_cell_measurement_theta_min     2.47
_cell_measurement_theta_max     27.30
_cell_measurement_temperature     173(2)
_exptl_crystal_description     block
_exptl_crystal_colour     yellow
_exptl_crystal_size_max     0.40
_exptl_crystal_size_mid     0.40
_exptl_crystal_size_min     0.20
_exptl_crystal_density_diffrn     1.342
_exptl_crystal_density_meas     'not measured'
_exptl_crystal_density_method     'not measured'
_exptl_crystal_F_000     270
_exptl_absorpt_coefficient_mu     0.105
_exptl_absorpt_correction_type     multi-scan
_exptl_absorpt_process_details     '(SADABS; Sheldrick, 2000)'
_exptl_absorpt_correction_T_min     0.959
_exptl_absorpt_correction_T_max     0.979
_exptl_special_details
;
 ?
;
_diffrn_ambient_temperature     173(2)
_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     'Bruker SMART 1K CCD area-detector'
_diffrn_measurement_method     ω
_diffrn_detector_area_resol_mean     ?
_diffrn_reflns_number     2974
_diffrn_reflns_av_R_equivalents     0.087
_diffrn_reflns_av_sigmaI/netI     0.085
_diffrn_reflns_theta_min     2.48
_diffrn_reflns_theta_max     25.00
_diffrn_reflns_theta_full     25.00
_diffrn_measured_fraction_theta_max     0.950
_diffrn_measured_fraction_theta_full     27.30
_diffrn_reflns_limit_h_min     -6
_diffrn_reflns_limit_h_max     8
_diffrn_reflns_limit_k_min     -10
_diffrn_reflns_limit_k_max     9
_diffrn_reflns_limit_l_min     -13
_diffrn_reflns_limit_l_max     13
_diffrn_standards_number     0
_diffrn_standards_interval_count     ?
_diffrn_standards_interval_time     ?
_diffrn_standards_decay_%     ?
_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     2115
_reflns_number_gt     1671
_reflns_threshold_expression     I>2σ(I)
_refine_ls_structure_factor_coef     Fsqd
_refine_ls_matrix_type     full
_refine_ls_R_factor_all     0.118
_refine_ls_R_factor_gt     0.097
_refine_ls_wR_factor_gt     0.212
_refine_ls_wR_factor_ref     0.222
_refine_ls_goodness_of_fit_ref     1.171
_refine_ls_restrained_S_all     1.171
_refine_ls_number_reflns     2115
_refine_ls_number_parameters     166
_refine_ls_number_restraints     0
_refine_ls_hydrogen_treatment     constr
_refine_ls_weighting_scheme     calc
_refine_ls_weighting_details
       'calc w = 1/[σ²(Fo²)+(0.0766P)²+0.6828P] 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     0.000
_refine_ls_shift/su_mean     0.000
_refine_diff_density_max     0.31
_refine_diff_density_min     -0.27
_refine_ls_extinction_method     none
_refine_ls_extinction_coef     ?
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     'SMART (Bruker, 2000)'
_computing_cell_refinement     'SAINT (Bruker, 2000)'
_computing_data_reduction     SAINT
_computing_structure_solution     'SHELXS97 (Sheldrick, 2000)'
_computing_structure_refinement     'SHELXL97 (Sheldrick, 2000)'
_computing_molecular_graphics     'SHELXTL/PC (Sheldrick, 1999)'
_computing_publication_material     SHELXTL/PC
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 0.0004(5) 0.3744(3) 0.6947(3) 0.0463(9) Uani d . 1 . . O
    O2 0.1067(6) 0.1326(4) 0.8150(3) 0.0613(11) Uani d . 1 . . O
    O3 0.3650(5) -0.1532(4) 0.3305(3) 0.0457(8) Uani d . 1 . . O
    N1 0.1682(5) 0.1383(4) 0.4171(3) 0.0285(8) Uani d . 1 . . N
    N2 0.0766(5) 0.2258(4) 0.7119(3) 0.0374(9) Uani d . 1 . . N
    N3 0.4569(5) -0.2941(4) 0.5280(3) 0.0324(8) Uani d . 1 . . N
    H3A 0.4520 -0.2902 0.6062 0.039 Uiso calc R 1 . . H
    C1 0.1576(7) 0.1880(5) 0.2808(4) 0.0423(11) Uani d . 1 . . C
    H1A 0.0772 0.3032 0.2533 0.063 Uiso calc R 1 . . H
    H1B 0.0926 0.1223 0.2466 0.063 Uiso calc R 1 . . H
    H1C 0.2960 0.1716 0.2520 0.063 Uiso calc R 1 . . H
    C2 0.2585(5) -0.0166(4) 0.4915(3) 0.0255(9) Uani d . 1 . . C
    C3 0.2347(5) -0.0049(4) 0.6115(4) 0.0285(9) Uani d . 1 . . C
    H3 0.2809 -0.0913 0.6832 0.034 Uiso calc R 1 . . H
    C4 0.1299(5) 0.1573(4) 0.6089(4) 0.0276(9) Uani d . 1 . . C
    C5 0.0903(5) 0.2431(4) 0.4866(4) 0.0282(9) Uani d . 1 . . C
    H5 0.0203 0.3561 0.4576 0.034 Uiso calc R 1 . . H
    C6 0.3619(6) -0.1587(5) 0.4420(4) 0.0296(9) Uani d . 1 . . C
    C7 0.5666(6) -0.4457(5) 0.4980(4) 0.0361(10) Uani d . 1 . . C
    H7A 0.6864 -0.5035 0.5573 0.043 Uiso calc R 1 . . H
    H7B 0.6175 -0.4231 0.4142 0.043 Uiso calc R 1 . . H
    C10 0.5194(10) 0.4689(6) 0.8312(5) 0.0687(17) Uani d . 1 . . C
    H10 0.6527 0.4321 0.8030 0.082 Uiso calc R 1 . . H
    O5 0.4225(7) 0.6105(4) 0.7889(3) 0.0728(12) Uani d . 1 . . O
    N4 0.4608(9) 0.3619(5) 0.9111(4) 0.0644(13) Uani d . 1 . . N
    C11 0.5852(16) 0.1957(8) 0.9564(7) 0.120(3) Uani d . 1 . . C
    H11A 0.7158 0.1774 0.9170 0.180 Uiso calc R 1 . . H
    H11B 0.5145 0.1234 0.9370 0.180 Uiso calc R 1 . . H
    H11C 0.6101 0.1728 1.0462 0.180 Uiso calc R 1 . . H
    C12 0.2548(11) 0.4103(10) 0.9565(6) 0.097(3) Uani d . 1 . . C
    H12A 0.1953 0.5290 0.9318 0.145 Uiso calc R 1 . . H
    H12B 0.2630 0.3741 1.0469 0.145 Uiso calc R 1 . . H
    H12C 0.1688 0.3601 0.9211 0.145 Uiso calc R 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
    N1 0.0315(17) 0.0252(17) 0.0278(17) -0.0125(14) -0.0013(13) 0.0009(14)
    O3 0.054(2) 0.0448(18) 0.0339(18) -0.0094(15) -0.0017(14) -0.0099(14)
    C6 0.025(2) 0.037(2) 0.034(2) -0.0189(17) 0.0017(16) -0.0090(18)
    C3 0.028(2) 0.0243(19) 0.033(2) -0.0138(16) -0.0028(16) 0.0008(16)
    O1 0.061(2) 0.0291(16) 0.0438(19) -0.0051(14) -0.0043(15) -0.0100(14)
    C2 0.0267(19) 0.0270(19) 0.026(2) -0.0188(16) -0.0034(15) 0.0028(15)
    N2 0.040(2) 0.0290(19) 0.041(2) -0.0092(15) -0.0051(16) -0.0063(16)
    N3 0.039(2) 0.0280(18) 0.0322(19) -0.0121(15) 0.0014(15) -0.0088(15)
    O2 0.098(3) 0.0384(19) 0.0336(19) -0.0065(18) -0.0042(18) -0.0028(15)
    C5 0.0243(19) 0.0204(19) 0.037(2) -0.0088(15) -0.0050(16) 0.0013(17)
    C7 0.032(2) 0.036(2) 0.041(2) -0.0132(18) 0.0020(18) -0.0084(19)
    C4 0.0243(19) 0.0216(19) 0.036(2) -0.0098(15) -0.0012(16) -0.0018(16)
    C1 0.056(3) 0.032(2) 0.032(2) -0.013(2) -0.002(2) 0.0060(19)
    C10 0.104(5) 0.046(3) 0.042(3) -0.010(3) 0.019(3) -0.005(3)
    N4 0.119(4) 0.046(2) 0.026(2) -0.029(3) -0.001(2) 0.0014(18)
    C11 0.229(10) 0.047(4) 0.058(4) -0.018(5) -0.001(5) 0.004(3)
    C12 0.103(6) 0.147(7) 0.053(4) -0.071(5) -0.002(4) -0.005(4)
    O5 0.117(3) 0.041(2) 0.044(2) -0.012(2) 0.008(2) 0.0039(17)
_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 . 1.331(5) y
    N1 C2 . 1.390(5) y
    N1 C1 . 1.476(5) y
    O3 C6 . 1.232(5) y
    C6 N3 . 1.339(5) y
    C6 C2 . 1.472(5) y
    C3 C2 . 1.368(5) y
    C3 C4 . 1.394(5) y
    C3 H3 . 0.9500 ?
    O1 N2 . 1.232(4) ?
    N2 O2 . 1.228(5) ?
    N2 C4 . 1.413(5) ?
    N3 C7 . 1.441(5) ?
    N3 H3A . 0.8800 ?
    C5 C4 . 1.383(5) y
    C5 H5 . 0.9500 ?
    C7 C7 2_646 1.520(8) ?
    C7 H7A . 0.9900 ?
    C7 H7B . 0.9900 ?
    C1 H1A . 0.9800 ?
    C1 H1B . 0.9800 ?
    C1 H1C . 0.9800 ?
    C10 O5 . 1.212(6) ?
    C10 N4 . 1.303(7) ?
    C10 H10 . 0.9500 ?
    N4 C11 . 1.436(8) ?
    N4 C12 . 1.469(8) ?
    C11 H11A . 0.9800 ?
    C11 H11B . 0.9800 ?
    C11 H11C . 0.9800 ?
    C12 H12A . 0.9800 ?
    C12 H12B . 0.9800 ?
    C12 H12C . 0.9800 ?
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 . . 110.2(3) y
    C5 N1 C1 . . 122.5(3) y
    C2 N1 C1 . . 127.3(3) y
    O3 C6 N3 . . 122.5(4) y
    O3 C6 C2 . . 122.9(4) ?
    N3 C6 C2 . . 114.6(4) ?
    C2 C3 C4 . . 107.2(3) ?
    C2 C3 H3 . . 126.4 ?
    C4 C3 H3 . . 126.4 ?
    C3 C2 N1 . . 107.0(3) ?
    C3 C2 C6 . . 129.8(3) ?
    N1 C2 C6 . . 123.2(3) ?
    O2 N2 O1 . . 123.2(4) ?
    O2 N2 C4 . . 117.7(3) ?
    O1 N2 C4 . . 119.1(3) ?
    C6 N3 C7 . . 122.9(4) ?
    C6 N3 H3A . . 118.5 ?
    C7 N3 H3A . . 118.5 ?
    N1 C5 C4 . . 107.4(3) ?
    N1 C5 H5 . . 126.3 ?
    C4 C5 H5 . . 126.3 ?
    N3 C7 C7 . 2_646 111.9(4) ?
    N3 C7 H7A . . 109.2 ?
    C7 C7 H7A 2_646 . 109.2 ?
    N3 C7 H7B . . 109.2 ?
    C7 C7 H7B 2_646 . 109.2 ?
    H7A C7 H7B . . 107.9 ?
    C5 C4 C3 . . 108.2(3) ?
    C5 C4 N2 . . 125.0(3) ?
    C3 C4 N2 . . 126.8(3) ?
    N1 C1 H1A . . 109.5 ?
    N1 C1 H1B . . 109.5 ?
    H1A C1 H1B . . 109.5 ?
    N1 C1 H1C . . 109.5 ?
    H1A C1 H1C . . 109.5 ?
    H1B C1 H1C . . 109.5 ?
    O5 C10 N4 . . 127.1(6) ?
    O5 C10 H10 . . 116.5 ?
    N4 C10 H10 . . 116.5 ?
    C10 N4 C11 . . 123.6(6) ?
    C10 N4 C12 . . 119.2(5) ?
    C11 N4 C12 . . 117.2(6) ?
    N4 C11 H11A . . 109.5 ?
    N4 C11 H11B . . 109.5 ?
    H11A C11 H11B . . 109.5 ?
    N4 C11 H11C . . 109.5 ?
    H11A C11 H11C . . 109.5 ?
    H11B C11 H11C . . 109.5 ?
    N4 C12 H12A . . 109.5 ?
    N4 C12 H12B . . 109.5 ?
    H12A C12 H12B . . 109.5 ?
    N4 C12 H12C . . 109.5 ?
    H12A C12 H12C . . 109.5 ?
    H12B C12 H12C . . 109.5 ?
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
    C4 C3 C2 N1 . . . . 0.0(4) y
    C4 C3 C2 C6 . . . . 178.4(4) ?
    C5 N1 C2 C3 . . . . -0.2(4) ?
    C1 N1 C2 C3 . . . . 179.0(4) ?
    C5 N1 C2 C6 . . . . -178.7(3) ?
    C1 N1 C2 C6 . . . . 0.4(6) ?
    O3 C6 C2 C3 . . . . 177.0(4) y
    N3 C6 C2 C3 . . . . -4.5(5) y
    O3 C6 C2 N1 . . . . -4.8(6) y
    N3 C6 C2 N1 . . . . 173.7(3) y
    O3 C6 N3 C7 . . . . -1.5(6) y
    C2 C6 N3 C7 . . . . -180.0(3) y
    C2 N1 C5 C4 . . . . 0.3(4) ?
    C1 N1 C5 C4 . . . . -178.9(3) ?
    C6 N3 C7 C7 . . . 2_646 -93.6(5) ?
    N1 C5 C4 C3 . . . . -0.3(4) ?
    N1 C5 C4 N2 . . . . 178.2(3) ?
    C2 C3 C4 C5 . . . . 0.2(4) ?
    C2 C3 C4 N2 . . . . -178.3(4) ?
    O2 N2 C4 C5 . . . . 174.2(4) ?
    O1 N2 C4 C5 . . . . -4.9(6) ?
    O2 N2 C4 C3 . . . . -7.6(6) ?
    O1 N2 C4 C3 . . . . 173.3(4) ?
    O5 C10 N4 C11 . . . . 179.8(6) ?
    O5 C10 N4 C12 . . . . 1.2(9) ?
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
    N3 H3A O5 1_545 0.88 2.06 2.860(5) 152
data_global
_journal_date_recd_electronic     2003-10-21
_journal_date_accepted     2003-11-17
_journal_name_full     'Acta Crystallographica, Section E'
_journal_year     2004
_journal_volume     60
_journal_issue      1
_journal_page_first     o35
_journal_page_last     o36
_journal_paper_category     EO
_publ_contact_author_name     'Professor P. Yang'
_publ_contact_author_address
;
Institute of Molecular Science
Chemical Biology and Molecular Engineering Laboratory of the Education Ministry
Shanxi University
Taiyuan
Shanxi 030006
People's Republic of China
;
_publ_contact_author_email     yangpin@sxu.edu.cn
_publ_contact_author_fax     '0086 351 701 1022'
_publ_contact_author_phone     '0086 351 701 0699'
_publ_section_title
;
1-Methyl-N-(2-{[(1-methyl-4-nitro-1H-pyrrol-2-yl)carbonyl]amino}ethyl)-
4-nitro-1H-pyrrole-2-carboxamide dimethylformamide disolvate
;
loop_
    _publ_author_name
    _publ_author_address
    'Lu, Li-Ping'
;
Institute of Molecular Science
Chemical Biology and Molecular Engineering Laboratory of the Education Ministry
Shanxi University
Taiyuan
Shanxi 030006
People's Republic of China
;
    'Zhu, Miao-Li'
;
Institute of Molecular Science
Chemical Biology and Molecular Engineering Laboratory of the Education Ministry
Shanxi University
Taiyuan
Shanxi 030006
People's Republic of China
;
    'Yang, Pin'
;
Institute of Molecular Science
Chemical Biology and Molecular Engineering Laboratory of the Education Ministry
Shanxi University
Taiyuan
Shanxi 030006
People's Republic of China
;
