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###                                                                        ###
###        Electronic paper (Acta Crystallographica Section E)             ###
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#                                                                            #
# 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 2.4.    #
#                                                                            #
# 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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# This file may be used for bona fide research purposes within the           #
# scientific community so long as proper attribution is given to the journal # 
# article from which it was obtained.                                        #
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data_I
_audit_creation_method     SHELXL-97
_chemical_name_systematic
;
N,N-Bis(cyanomethyl)nitrous amide
;
_chemical_name_common     ?
_chemical_formula_moiety     'C4 H4 N4 O'
_chemical_formula_sum     'C4 H4 N4 O'
_chemical_formula_iupac     'C4 H4 N4 O'
_chemical_formula_weight     124.11
_chemical_melting_point     ?
_symmetry_cell_setting     'Monoclinic'
_symmetry_space_group_name_H-M     'P 21/c'
_symmetry_space_group_name_Hall     '-P 2ybc'
loop_
    _symmetry_equiv_pos_as_xyz
    'x, y, z'
    '-x, y+1/2, -z+1/2'
    '-x, -y, -z'
    'x, -y-1/2, z-1/2'
_cell_length_a     6.5622(13)
_cell_length_b     8.9765(18)
_cell_length_c     11.008(4)
_cell_angle_alpha     90.00
_cell_angle_beta     108.55(3)
_cell_angle_gamma     90.00
_cell_volume     614.7(3)
_cell_formula_units_Z     4
_cell_measurement_reflns_used     1409
_cell_measurement_theta_min     2.2761
_cell_measurement_theta_max     27.480
_cell_measurement_temperature     293(2)
_exptl_crystal_description     'Prism'
_exptl_crystal_colour     'Colorless'
_exptl_crystal_size_max     0.2000
_exptl_crystal_size_mid     0.2000
_exptl_crystal_size_min     0.2000
_exptl_crystal_density_diffrn     1.341
_exptl_crystal_density_meas     ?
_exptl_crystal_density_method     'not measured'
_exptl_crystal_F_000     256
_exptl_absorpt_coefficient_mu     0.104
_exptl_absorpt_correction_type     'Multi-scan'
_exptl_absorpt_process_details     '(CrystalClear; Rigaku, 2005)'
_exptl_absorpt_correction_T_min     0.7421
_exptl_absorpt_correction_T_max     1.0000
_exptl_special_details
;
;
_diffrn_ambient_temperature     293(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     'Rigaku Mercury2'
_diffrn_measurement_method     'CCD_Profile_fitting'
_diffrn_detector_area_resol_mean     13.6612
_diffrn_reflns_number     6154
_diffrn_reflns_av_R_equivalents     0.0594
_diffrn_reflns_av_sigmaI/netI     0.0478
_diffrn_reflns_theta_min     2.99
_diffrn_reflns_theta_max     27.45
_diffrn_reflns_theta_full     27.45
_diffrn_measured_fraction_theta_max     0.997
_diffrn_measured_fraction_theta_full     0.997
_diffrn_reflns_limit_h_min     -8
_diffrn_reflns_limit_h_max     8
_diffrn_reflns_limit_k_min     -11
_diffrn_reflns_limit_k_max     11
_diffrn_reflns_limit_l_min     -14
_diffrn_reflns_limit_l_max     14
_diffrn_standards_number     ?
_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 >
σ(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     1408
_reflns_number_gt     1094
_reflns_threshold_expression     I>2σ(I)
_refine_ls_structure_factor_coef     Fsqd
_refine_ls_matrix_type     full
_refine_ls_R_factor_all     0.0634
_refine_ls_R_factor_gt     0.0499
_refine_ls_wR_factor_gt     0.1494
_refine_ls_wR_factor_ref     0.1623
_refine_ls_goodness_of_fit_ref     1.054
_refine_ls_restrained_S_all     1.054
_refine_ls_number_reflns     1408
_refine_ls_number_parameters     83
_refine_ls_number_restraints     0
_refine_ls_hydrogen_treatment     constr
_refine_ls_weighting_scheme     calc
_refine_ls_weighting_details
                   'calc w=1/[σ²(Fo²)+(0.10P)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     0.000
_refine_ls_shift/su_mean     0.000
_refine_diff_density_max     0.20
_refine_diff_density_min     -0.20
_refine_ls_extinction_method     'SHELXL97 (Sheldrick, 2008)'
_refine_ls_extinction_coef     0.15(2)
_refine_ls_extinction_expression
                                  'Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^'
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     'CrystalClear (Rigaku, 2005)'
_computing_cell_refinement     'CrystalClear (Rigaku, 2005)'
_computing_data_reduction     'CrystalClear (Rigaku, 2005)'
_computing_structure_solution     'SHELXS97 (Sheldrick, 2008)'
_computing_structure_refinement     'SHELXL97 (Sheldrick, 2008)'
_computing_molecular_graphics     'SHELXTL (Sheldrick, 2008)'
_computing_publication_material     'SHELXTL (Sheldrick, 2008)'
loop_
    _atom_site_type_symbol
    _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
    O O1 0.1721(2) -0.00421(14) 0.24979(14) 0.0738(5) Uani d . 1 . .
    N N1 0.1213(3) 0.3227(2) 0.03826(14) 0.0730(6) Uani d . 1 . .
    N N2 0.6354(3) 0.36079(17) 0.61699(14) 0.0593(5) Uani d . 1 . .
    N N3 0.3553(2) 0.02971(15) 0.31634(14) 0.0537(5) Uani d . 1 . .
    N N4 0.38510(18) 0.17474(12) 0.33544(10) 0.0345(4) Uani d . 1 . .
    C C2 0.6201(2) 0.29919(17) 0.52436(14) 0.0411(4) Uani d . 1 . .
    C C1 0.6039(2) 0.22069(18) 0.40327(13) 0.0419(4) Uani d . 1 . .
    H H1A 0.6543 0.2860 0.3487 0.050 Uiso calc R 1 . .
    H H1B 0.6962 0.1336 0.4222 0.050 Uiso calc R 1 . .
    C C4 0.1609(2) 0.30241(19) 0.14509(15) 0.0439(4) Uani d . 1 . .
    C C3 0.2111(2) 0.28025(16) 0.28328(13) 0.0405(4) Uani d . 1 . .
    H H3B 0.2504 0.3752 0.3264 0.049 Uiso calc R 1 . .
    H H3C 0.0835 0.2446 0.3006 0.049 Uiso calc R 1 . .
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
    O1 0.0564(9) 0.0523(9) 0.0991(11) -0.0192(6) 0.0056(7) -0.0124(6)
    N1 0.0569(11) 0.1157(16) 0.0448(9) 0.0196(9) 0.0140(7) 0.0171(8)
    N2 0.0655(11) 0.0593(10) 0.0484(8) -0.0107(8) 0.0113(7) -0.0105(7)
    N3 0.0509(9) 0.0336(8) 0.0697(10) -0.0029(6) 0.0094(7) -0.0008(6)
    N4 0.0342(7) 0.0298(7) 0.0356(7) 0.0010(5) 0.0056(5) 0.0001(4)
    C2 0.0369(8) 0.0392(8) 0.0407(8) -0.0047(6) 0.0032(6) 0.0029(6)
    C1 0.0357(9) 0.0485(9) 0.0387(8) -0.0044(7) 0.0076(6) -0.0030(6)
    C4 0.0339(8) 0.0545(9) 0.0390(9) 0.0035(7) 0.0058(6) 0.0048(6)
    C3 0.0449(9) 0.0372(8) 0.0352(8) 0.0099(6) 0.0067(6) -0.0017(6)
_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
    O1 N3 . 1.2305(18) ?
    N1 C4 . 1.135(2) ?
    N2 C2 . 1.136(2) ?
    N3 N4 . 1.3233(18) ?
    N4 C1 . 1.4516(18) ?
    N4 C3 . 1.4539(17) ?
    C2 C1 . 1.481(2) ?
    C1 H1A . 0.9700 ?
    C1 H1B . 0.9700 ?
    C4 C3 . 1.464(2) ?
    C3 H3B . 0.9700 ?
    C3 H3C . 0.9700 ?
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
    O1 N3 N4 . . 113.89(13) ?
    N3 N4 C1 . . 115.67(12) ?
    N3 N4 C3 . . 121.36(12) ?
    C1 N4 C3 . . 122.83(12) ?
    N2 C2 C1 . . 178.83(17) ?
    N4 C1 C2 . . 111.97(13) ?
    N4 C1 H1A . . 109.2 ?
    C2 C1 H1A . . 109.2 ?
    N4 C1 H1B . . 109.2 ?
    C2 C1 H1B . . 109.2 ?
    H1A C1 H1B . . 107.9 ?
    N1 C4 C3 . . 178.53(19) ?
    N4 C3 C4 . . 112.80(12) ?
    N4 C3 H3B . . 109.0 ?
    C4 C3 H3B . . 109.0 ?
    N4 C3 H3C . . 109.0 ?
    C4 C3 H3C . . 109.0 ?
    H3B C3 H3C . . 107.8 ?
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
    C3 H3B N2 3_666 0.97 2.50 3.450(2) 165
    C3 H3C N1 4_566 0.97 2.62 3.183(2) 117
data_global
_journal_date_recd_electronic     2010-05-06
_journal_date_accepted     2010-05-11
_journal_name_full     'Acta Crystallographica, Section E'
_journal_year     2010
_journal_volume     66
_journal_issue      6
_journal_page_first     o1362
_journal_page_last     o1362
_journal_paper_category     QO
_journal_coeditor_code     PV2279
_publ_contact_author_name     'Yuan Zhang*'
_publ_contact_author_address
;
Ordered Matter Science Research Center,
College of Chemistry and Chemical,
Engineering, Southeast UniVersity,
Nanjing 211189, People's Republic of China
;
_publ_contact_author_email     zhangshelley86@hotmail.com
_publ_contact_author_fax     ?
_publ_contact_author_phone     ?
_publ_section_title
;
N,N-Bis(cyanomethyl)nitrous amide
;
loop_
    _publ_author_name
    _publ_author_footnote
    _publ_author_address
    'Zhang, Yuan' .
;
Ordered Matter Science Research Center
College of Chemistry and Chemical Engineering
Southeast University
Nanjing 211189
People's Republic of China
;
    'Han, Meng Ting' .
;
Ordered Matter Science Research Center
College of Chemistry and Chemical Engineering
Southeast University
Nanjing 211189
People's Republic of China
;
