##############################################################################
###                                                                        ###
###           Full Paper (Acta Crystallographica Section C)                ###
###                                                                        ###
##############################################################################
#                                                                            #
# 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/  #
# cif/home.html                                                              #
#                                                                            #
#            Copyright International Union of Crystallography                #
#                                                                            #
##############################################################################
data_IV
_audit_creation_method     SHELXL-97
_chemical_name_systematic
;
N⁴-(Pyrrol-1-yl)-1,2,4-triazole
;
_chemical_name_common     ?
_chemical_formula_moiety     'C6 H6 N4'
_chemical_formula_sum     'C6 H6 N4'
_chemical_formula_iupac     'C6 H6 N4'
_chemical_formula_weight     134.15
_chemical_melting_point     408
_symmetry_cell_setting     monoclinic
_symmetry_space_group_name_H-M     'C 2/c'
_symmetry_space_group_name_Hall     '-C 2yc'
loop_
    _symmetry_equiv_pos_as_xyz
    'x, y, z'
    '-x, y, -z+1/2'
    'x+1/2, y+1/2, z'
    '-x+1/2, y+1/2, -z+1/2'
    '-x, -y, -z'
    'x, -y, z-1/2'
    '-x+1/2, -y+1/2, -z'
    'x+1/2, -y+1/2, z-1/2'
_cell_length_a     22.9326(11)
_cell_length_b     12.1235(6)
_cell_length_c     7.0111(3)
_cell_angle_alpha     90.00
_cell_angle_beta     96.707(2)
_cell_angle_gamma     90.00
_cell_volume     1935.91(16)
_cell_formula_units_Z     12
_cell_measurement_reflns_used     5988
_cell_measurement_theta_min     2.926
_cell_measurement_theta_max     26.4345
_cell_measurement_temperature     93(2)
_exptl_crystal_description     block
_exptl_crystal_colour     colourless
_exptl_crystal_size_max     0.5
_exptl_crystal_size_mid     0.3
_exptl_crystal_size_min     0.1
_exptl_crystal_density_diffrn     1.381
_exptl_crystal_density_meas     ?
_exptl_crystal_density_method     'not measured'
_exptl_crystal_F_000     840
_exptl_absorpt_coefficient_mu     0.094
_exptl_absorpt_correction_type     'multi-scan'
_exptl_absorpt_process_details     '(SCALE; Bruker, 2004)'
_exptl_absorpt_correction_T_min     0.83421
_exptl_absorpt_correction_T_max     1.000
_exptl_special_details
;
¹H NMR (500 MHz, CDCl₃): 8.44 (2H, s, TrH), 6.88 (2H, t,
³J = 2 Hz, PyrH) and 6.33 (2H, t, ³J = 2 Hz, PyrH)
p.p.m.. ¹³C NMR (125 MHz, CDCl₃): 142.4 (Tr), 121.4 (Pyr) and 109.7 (Pyr)
p.p.m..
A sample was sublimed by warming to 50°C at <1 mmHg. Microanalysis: C, 53.72;
H, 4.56; N, 41.72%. Calc'd for C₆H₆N₄: C, 53.72; H, 4.51; N, 41.77%.
;
_diffrn_ambient_temperature     93(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 Kappa APEX II area-detector'
_diffrn_measurement_method     'φ amd ω'
_diffrn_reflns_number     20165
_diffrn_reflns_av_R_equivalents     0.0395
_diffrn_reflns_av_sigmaI/netI     0.0199
_diffrn_reflns_theta_min     1.90
_diffrn_reflns_theta_max     26.46
_diffrn_reflns_theta_full     26.46
_diffrn_measured_fraction_theta_max     0.993
_diffrn_measured_fraction_theta_full     0.993
_diffrn_reflns_limit_h_min     -28
_diffrn_reflns_limit_h_max     28
_diffrn_reflns_limit_k_min     -15
_diffrn_reflns_limit_k_max     15
_diffrn_reflns_limit_l_min     -8
_diffrn_reflns_limit_l_max     8
_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.
 There are no solvent molecules present and there is no disorder. All
 non-hydrogen atoms were refined anisotropically. The coordinates and U(iso)
 values for the hydrogen atoms were freely refined.
;
_reflns_number_total     1997
_reflns_number_gt     1834
_reflns_threshold_expression     I>2σ(I)
_refine_ls_structure_factor_coef     Fsqd
_refine_ls_matrix_type     full
_refine_ls_R_factor_all     0.0391
_refine_ls_R_factor_gt     0.0356
_refine_ls_wR_factor_gt     0.0866
_refine_ls_wR_factor_ref     0.0893
_refine_ls_goodness_of_fit_ref     1.102
_refine_ls_restrained_S_all     1.102
_refine_ls_number_reflns     1997
_refine_ls_number_parameters     173
_refine_ls_number_restraints     0
_refine_ls_hydrogen_treatment     refall
_refine_ls_weighting_scheme     calc
_refine_ls_weighting_details
         'calc w=1/[σ²(Fo²)+(0.0314P)²+1.7122P] 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     0.181
_refine_diff_density_min     -0.253
_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'
_computing_data_collection     'SMART (Bruker, 2004)'
_computing_cell_refinement     'SMART and SAINT (Bruker, 2004)'
_computing_data_reduction     'SAINT (Bruker, 2004)'
_computing_structure_solution     'SHELXS97 (Sheldrick, 1997)'
_computing_structure_refinement     'SHELXL97 (Sheldrick, 1997)'
_computing_molecular_graphics     'SHELXTL (Bruker, 2004)'
_computing_publication_material
                             'enCIFer (Version 1.2; Allen et al.,  2004)'
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
    N N1 0.17185(5) 0.42851(9) 0.02172(16) 0.0267(3) Uani d . 1 . .
    N N2 0.17322(5) 0.34209(9) -0.11132(15) 0.0262(3) Uani d . 1 . .
    C C3 0.17229(5) 0.25021(11) -0.01590(17) 0.0225(3) Uani d . 1 . .
    H H3 0.1727(6) 0.1748(12) -0.065(2) 0.025(4) Uiso d . 1 . .
    N N4 0.17107(4) 0.27229(8) 0.17455(13) 0.0191(2) Uani d . 1 . .
    C C5 0.17085(5) 0.38400(10) 0.19046(18) 0.0227(3) Uani d . 1 . .
    H H5 0.1690(6) 0.4220(12) 0.307(2) 0.029(4) Uiso d . 1 . .
    N N11 0.16928(4) 0.19687(8) 0.32121(14) 0.0197(2) Uani d . 1 . .
    C C12 0.12008(6) 0.17326(11) 0.40916(18) 0.0261(3) Uani d . 1 . .
    H H12 0.0856(7) 0.2117(13) 0.376(2) 0.035(4) Uiso d . 1 . .
    C C13 0.13635(6) 0.09477(12) 0.54369(18) 0.0286(3) Uani d . 1 . .
    H H13 0.1108(7) 0.0638(13) 0.628(2) 0.035(4) Uiso d . 1 . .
    C C14 0.19646(6) 0.07027(11) 0.53655(18) 0.0253(3) Uani d . 1 . .
    H H14 0.2202(7) 0.0188(13) 0.614(2) 0.036(4) Uiso d . 1 . .
    C C15 0.21639(5) 0.13478(10) 0.39869(16) 0.0203(3) Uani d . 1 . .
    H H15 0.2537(6) 0.1425(12) 0.352(2) 0.025(4) Uiso d . 1 . .
    N N22 0.02906(5) 0.57318(9) 0.72689(16) 0.0295(3) Uani d . 1 . .
    C C23 0.04474(6) 0.47055(11) 0.71337(17) 0.0250(3) Uani d . 1 . .
    H H23 0.0815(7) 0.4429(12) 0.682(2) 0.029(4) Uiso d . 1 . .
    N N24 0.0000 0.40305(12) 0.7500 0.0223(3) Uani d S 1 . .
    N N31 0.0000 0.28962(13) 0.7500 0.0267(3) Uani d S 1 . .
    C C32 0.02309(6) 0.22582(13) 0.9026(2) 0.0357(3) Uani d . 1 . .
    H H32 0.0387(8) 0.2610(15) 1.014(3) 0.044(5) Uiso d . 1 . .
    C C33 0.01472(7) 0.11950(14) 0.8446(3) 0.0519(5) Uani d . 1 . .
    H H33 0.0266(9) 0.0574(17) 0.920(3) 0.062(6) Uiso d . 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
    N1 0.0269(6) 0.0245(5) 0.0273(6) -0.0010(4) -0.0018(4) 0.0033(4)
    N2 0.0267(6) 0.0298(6) 0.0219(5) 0.0001(4) 0.0016(4) 0.0032(4)
    C3 0.0232(6) 0.0260(6) 0.0183(6) 0.0004(5) 0.0021(4) -0.0008(5)
    N4 0.0204(5) 0.0202(5) 0.0163(5) 0.0008(4) 0.0004(4) 0.0013(4)
    C5 0.0222(6) 0.0214(6) 0.0236(6) 0.0018(5) -0.0019(5) -0.0005(5)
    N11 0.0206(5) 0.0217(5) 0.0166(5) 0.0000(4) 0.0018(4) 0.0022(4)
    C12 0.0215(6) 0.0343(7) 0.0230(6) -0.0023(5) 0.0049(5) -0.0022(5)
    C13 0.0318(7) 0.0354(7) 0.0192(6) -0.0098(6) 0.0055(5) 0.0001(5)
    C14 0.0321(7) 0.0231(6) 0.0196(6) -0.0031(5) -0.0017(5) 0.0016(5)
    C15 0.0217(6) 0.0198(6) 0.0186(5) 0.0008(5) -0.0006(4) -0.0012(4)
    N22 0.0304(6) 0.0291(6) 0.0273(6) -0.0028(5) -0.0037(4) 0.0004(4)
    C23 0.0232(6) 0.0297(7) 0.0209(6) -0.0026(5) -0.0029(5) 0.0008(5)
    N24 0.0225(7) 0.0231(7) 0.0205(7) 0.000 -0.0018(5) 0.000
    N31 0.0242(8) 0.0228(8) 0.0330(8) 0.000 0.0030(6) 0.000
    C32 0.0266(7) 0.0342(8) 0.0482(9) 0.0065(6) 0.0122(6) 0.0160(7)
    C33 0.0402(9) 0.0301(8) 0.0918(14) 0.0082(7) 0.0346(9) 0.0177(8)
_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 . 1.3030(16) ?
    N1 N2 . 1.4056(15) y
    N2 C3 . 1.3008(16) ?
    C3 N4 . 1.3653(15) ?
    C3 H3 . 0.978(15) ?
    N4 C5 . 1.3589(16) ?
    N4 N11 . 1.3802(13) y
    C5 H5 . 0.942(16) ?
    N11 C15 . 1.3755(15) ?
    N11 C12 . 1.3776(15) ?
    C12 C13 . 1.3610(19) ?
    C12 H12 . 0.923(16) ?
    C13 C14 . 1.4168(19) ?
    C13 H13 . 0.959(16) ?
    C14 C15 . 1.3631(17) ?
    C14 H14 . 0.954(17) ?
    C15 H15 . 0.955(15) ?
    N22 C23 . 1.3017(17) ?
    N22 N22 2_556 1.408(2) y
    C23 N24 . 1.3601(15) ?
    C23 H23 . 0.956(15) ?
    N24 C23 2_556 1.3601(15) ?
    N24 N31 . 1.375(2) y
    N31 C32 2_556 1.3753(17) ?
    N31 C32 . 1.3753(17) ?
    C32 C33 . 1.358(2) ?
    C32 H32 . 0.926(18) ?
    C33 C33 2_556 1.417(4) ?
    C33 H33 . 0.94(2) ?
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 N2 . . 107.34(10) ?
    C3 N2 N1 . . 107.10(10) ?
    N2 C3 N4 . . 109.79(11) ?
    N2 C3 H3 . . 128.2(9) ?
    N4 C3 H3 . . 122.0(9) ?
    C5 N4 C3 . . 106.05(10) ?
    C5 N4 N11 . . 126.75(10) ?
    C3 N4 N11 . . 127.20(10) ?
    N1 C5 N4 . . 109.73(11) ?
    N1 C5 H5 . . 126.2(9) ?
    N4 C5 H5 . . 124.1(9) ?
    C15 N11 C12 . . 110.87(10) ?
    C15 N11 N4 . . 124.50(10) ?
    C12 N11 N4 . . 124.63(10) ?
    C13 C12 N11 . . 106.43(11) ?
    C13 C12 H12 . . 133.0(10) ?
    N11 C12 H12 . . 120.4(10) ?
    C12 C13 C14 . . 108.13(11) ?
    C12 C13 H13 . . 124.4(10) ?
    C14 C13 H13 . . 127.4(10) ?
    C15 C14 C13 . . 108.24(11) ?
    C15 C14 H14 . . 124.1(10) ?
    C13 C14 H14 . . 127.7(10) ?
    C14 C15 N11 . . 106.32(11) ?
    C14 C15 H15 . . 133.4(9) ?
    N11 C15 H15 . . 120.3(9) ?
    C23 N22 N22 . 2_556 107.08(7) ?
    N22 C23 N24 . . 109.90(12) ?
    N22 C23 H23 . . 127.6(9) ?
    N24 C23 H23 . . 122.5(9) ?
    C23 N24 C23 . 2_556 106.03(15) ?
    C23 N24 N31 . . 126.99(8) ?
    C23 N24 N31 2_556 . 126.99(8) ?
    N24 N31 C32 . 2_556 124.22(9) ?
    N24 N31 C32 . . 124.22(9) ?
    C32 N31 C32 2_556 . 111.56(18) ?
    C33 C32 N31 . . 105.82(16) ?
    C33 C32 H32 . . 135.8(11) ?
    N31 C32 H32 . . 118.3(11) ?
    C32 C33 C33 . 2_556 108.40(11) ?
    C32 C33 H33 . . 124.5(13) ?
    C33 C33 H33 2_556 . 127.1(13) ?
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 N2 C3 . . . . 0.71(13) ?
    N1 N2 C3 N4 . . . . -0.71(13) ?
    N2 C3 N4 C5 . . . . 0.46(13) ?
    N2 C3 N4 N11 . . . . 179.33(10) ?
    N2 N1 C5 N4 . . . . -0.43(13) ?
    C3 N4 C5 N1 . . . . 0.01(13) ?
    N11 N4 C5 N1 . . . . -178.87(10) ?
    C5 N4 N11 C15 . . . . -106.22(14) ?
    C3 N4 N11 C15 . . . . 75.14(16) y
    C5 N4 N11 C12 . . . . 74.08(16) y
    C3 N4 N11 C12 . . . . -104.57(14) ?
    C15 N11 C12 C13 . . . . -0.23(14) ?
    N4 N11 C12 C13 . . . . 179.51(11) ?
    N11 C12 C13 C14 . . . . -0.16(14) ?
    C12 C13 C14 C15 . . . . 0.49(15) ?
    C13 C14 C15 N11 . . . . -0.61(14) ?
    C12 N11 C15 C14 . . . . 0.53(14) ?
    N4 N11 C15 C14 . . . . -179.21(10) ?
    N22 N22 C23 N24 2_556 . . . -0.52(15) ?
    N22 C23 N24 C23 . . . 2_556 0.21(6) ?
    N22 C23 N24 N31 . . . . -179.79(6) ?
    C23 N24 N31 C32 . . . 2_556 -97.27(9) ?
    C23 N24 N31 C32 2_556 . . 2_556 82.73(9) ?
    C23 N24 N31 C32 . . . . 82.73(9) y
    C23 N24 N31 C32 2_556 . . . -97.27(9) ?
    N24 N31 C32 C33 . . . . -179.63(8) ?
    C32 N31 C32 C33 2_556 . . . 0.37(8) ?
    N31 C32 C33 C33 . . . 2_556 -0.9(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
    _geom_hbond_publ_flag
    C5 H5 N1 6_566 0.942(16) 2.353(16) 3.2479(16) 158.6(12) y
    C15 H15 N2 7 0.955(15) 2.521(15) 3.4261(16) 158.3(11) y
    C32 H32 N22 6_566 0.926(18) 2.528(18) 3.325(2) 144.3(14) y
data_global
_journal_date_recd_electronic     2007-03-29
_journal_date_accepted     2007-04-23
_journal_name_full     'Acta Crystallographica, Section C'
_journal_year     2007
_journal_volume     63
_journal_issue      6
_journal_page_first     o358
_journal_page_last     o360
_journal_paper_category     FO
_journal_coeditor_code     GA3049
_publ_contact_author_name     'Sally Brooker'
_publ_contact_author_address
;
Department of Chemistry, University of Otago, PO Box 56, Dunedin, New Zealand
;
_publ_contact_author_email     sbrooker@chemistry.otago.ac.nz
_publ_contact_author_fax     '+64 3 479 7906'
_publ_contact_author_phone     '+64 3 479 7919'
_publ_section_title
;
N⁴-(Pyrrol-1-yl)-1,2,4-triazole
;
loop_
    _publ_author_name
    _publ_author_address
    'Hellyer, Ryan M.'
;
Department of Chemistry, University of Otago, PO Box 56, Dunedin,
New Zealand
;
    'Joule, John A.'
;
The School of Chemistry, The University of Manchester,
Manchester M13 9PL, England
;
    'Larsen, David S.'
;
Department of Chemistry, University of Otago, PO Box 56, Dunedin,
New Zealand
;
    'Brooker, Sally'
;
Department of Chemistry, University of Otago, PO Box 56, Dunedin,
New Zealand
;
_publ_section_synopsis     .
