##############################################################################
#                                                                            #
# 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 Acta Crystallographica 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.                                       #
#                                                                            #
# Software is freely available for graphical display of the structure(s)     #
# in this CIF. For information consult the CIF software page                 #
# http://www.iucr.org/resources/cif/software.                                #
#                                                                            #
# 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.                                        #
#                                                                            #
##############################################################################
data_I
_audit_creation_method     SHELXL-97
_database_code_depnum_ccdc_archive     'CCDC 965650'
_chemical_name_systematic
;
3-Methyl-4-(2-phenyl-1,2,4-triazolo[1,5-a]pyrimidin-7-yl)furazan
;
_chemical_name_common     ?
_chemical_formula_moiety     'C14 H10 N6 O'
_chemical_formula_sum     'C14 H10 N6 O'
_chemical_formula_iupac     'C14 H10 N6 O'
_chemical_formula_weight     278.28
_chemical_melting_point_gt     483
_chemical_melting_point_lt     482
_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     11.1397(6)
_cell_length_b     15.6579(8)
_cell_length_c     7.3952(4)
_cell_angle_alpha     90.00
_cell_angle_beta     101.3320(10)
_cell_angle_gamma     90.00
_cell_volume     1264.76(12)
_cell_formula_units_Z     4
_cell_measurement_reflns_used     7123
_cell_measurement_theta_min     2.27
_cell_measurement_theta_max     31.04
_cell_measurement_temperature     120(2)
_cell_special_details     ?
_exptl_crystal_description     'prizm'
_exptl_crystal_colour     'colourless'
_exptl_crystal_size_max     0.32
_exptl_crystal_size_mid     0.28
_exptl_crystal_size_min     0.26
_exptl_crystal_density_diffrn     1.461
_exptl_crystal_density_meas     ?
_exptl_crystal_density_method     'not measured'
_exptl_crystal_F_000     576
_exptl_absorpt_coefficient_mu     0.100
_exptl_absorpt_correction_type     none
_exptl_absorpt_process_details     ?
_exptl_absorpt_correction_T_min     ?
_exptl_absorpt_correction_T_max     ?
_exptl_special_details     ?
_diffrn_ambient_temperature     120(2)
_diffrn_radiation_type     MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_source     'sealed tube'
_diffrn_radiation_monochromator     graphite
_diffrn_measurement_device_type     'Bruker APEXII CCD'
_diffrn_measurement_method     'φ and ω scans'
_diffrn_detector_area_resol_mean     ?
_diffrn_reflns_number     16844
_diffrn_reflns_av_R_equivalents     0.0301
_diffrn_reflns_av_sigmaI/netI     0.0252
_diffrn_reflns_theta_min     1.86
_diffrn_reflns_theta_max     31.04
_diffrn_reflns_theta_full     31.04
_diffrn_measured_fraction_theta_max     0.998
_diffrn_measured_fraction_theta_full     0.998
_diffrn_reflns_limit_h_min     -16
_diffrn_reflns_limit_h_max     16
_diffrn_reflns_limit_k_min     -22
_diffrn_reflns_limit_k_max     21
_diffrn_reflns_limit_l_min     -10
_diffrn_reflns_limit_l_max     10
_diffrn_standards_number     0
_diffrn_standards_interval_count     ?
_diffrn_standards_interval_time     ?
_diffrn_standards_decay_%     0
_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     4041
_reflns_number_gt     3456
_reflns_threshold_expression     I>2σ(I)
_refine_ls_structure_factor_coef     Fsqd
_refine_ls_matrix_type     full
_refine_ls_R_factor_all     0.0498
_refine_ls_R_factor_gt     0.0419
_refine_ls_wR_factor_gt     0.1110
_refine_ls_wR_factor_ref     0.1176
_refine_ls_goodness_of_fit_ref     1.024
_refine_ls_restrained_S_all     1.024
_refine_ls_number_reflns     4041
_refine_ls_number_parameters     191
_refine_ls_number_restraints     0
_refine_ls_hydrogen_treatment     constr
_refine_ls_weighting_scheme     calc
_refine_ls_weighting_details
         'calc w=1/[σ²(Fo²)+(0.0678P)²+0.3512P] 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     0.421
_refine_diff_density_min     -0.282
_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     'APEX2 (Bruker, 2009)'
_computing_cell_refinement     'SAINT (Bruker, 2009)'
_computing_data_reduction     'SAINT (Bruker, 2009)'
_computing_structure_solution     'SHELXTL (Sheldrick, 2008)'
_computing_structure_refinement     'SHELXTL (Sheldrick, 2008)'
_computing_molecular_graphics     'SHELXTL (Sheldrick, 2008)'
_computing_publication_material
    'SHELXTL (Sheldrick, 2008), publCIF (Westrip, 2010) and PLATON (Spek, 2009)'
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_symmetry_multiplicity
    _atom_site_disorder_assembly
    _atom_site_disorder_group
    O O1 0.56608(7) 0.23558(5) 0.09319(14) 0.0282(2) Uani d . 1 1 . .
    N N1 1.00892(7) -0.06092(5) 0.21751(12) 0.01583(17) Uani d . 1 1 . .
    N N2 0.82706(8) -0.11973(6) 0.02377(12) 0.01834(18) Uani d . 1 1 . .
    N N3 0.84903(7) 0.02462(5) 0.13466(11) 0.01300(16) Uani d . 1 1 . .
    N N4 0.93391(7) 0.07409(5) 0.24376(11) 0.01399(16) Uani d . 1 1 . .
    N N5 0.58150(8) 0.14848(6) 0.09470(14) 0.0227(2) Uani d . 1 1 . .
    N N6 0.67069(8) 0.27675(6) 0.06085(15) 0.0239(2) Uani d . 1 1 . .
    C C1 1.02813(8) 0.01935(6) 0.28809(13) 0.01377(17) Uani d . 1 1 . .
    C C2 0.89448(9) -0.05739(6) 0.12102(13) 0.01468(18) Uani d . 1 1 . .
    C C3 0.71487(9) -0.09738(6) -0.05783(14) 0.01883(19) Uani d . 1 1 . .
    H H3A 0.6646 -0.1399 -0.1265 0.023 Uiso calc R 1 1 . .
    C C4 0.66417(9) -0.01483(6) -0.05042(13) 0.01698(19) Uani d . 1 1 . .
    H H4A 0.5829 -0.0031 -0.1129 0.020 Uiso calc R 1 1 . .
    C C5 0.73399(8) 0.04786(6) 0.04821(13) 0.01414(17) Uani d . 1 1 . .
    C C6 1.14510(8) 0.04615(6) 0.40276(13) 0.01413(17) Uani d . 1 1 . .
    C C7 1.23825(9) -0.01412(6) 0.45314(14) 0.01694(19) Uani d . 1 1 . .
    H H7A 1.2241 -0.0721 0.4178 0.020 Uiso calc R 1 1 . .
    C C8 1.35164(9) 0.01047(7) 0.55480(15) 0.0205(2) Uani d . 1 1 . .
    H H8A 1.4147 -0.0307 0.5887 0.025 Uiso calc R 1 1 . .
    C C9 1.37265(10) 0.09538(8) 0.60680(16) 0.0247(2) Uani d . 1 1 . .
    H H9A 1.4504 0.1124 0.6748 0.030 Uiso calc R 1 1 . .
    C C10 1.27942(10) 0.15534(7) 0.55890(17) 0.0262(2) Uani d . 1 1 . .
    H H10A 1.2935 0.2132 0.5960 0.031 Uiso calc R 1 1 . .
    C C11 1.16591(9) 0.13117(7) 0.45715(15) 0.0202(2) Uani d . 1 1 . .
    H H11A 1.1027 0.1724 0.4247 0.024 Uiso calc R 1 1 . .
    C C12 0.69232(9) 0.13591(6) 0.06503(13) 0.01574(18) Uani d . 1 1 . .
    C C13 0.74940(9) 0.21662(6) 0.04368(14) 0.01690(19) Uani d . 1 1 . .
    C C14 0.87253(9) 0.23617(7) 0.00342(15) 0.0197(2) Uani d . 1 1 . .
    H H14A 0.8730 0.2945 -0.0444 0.030 Uiso calc R 1 1 . .
    H H14B 0.8910 0.1958 -0.0887 0.030 Uiso calc R 1 1 . .
    H H14C 0.9345 0.2310 0.1169 0.030 Uiso calc R 1 1 . .
_geom_special_details
;
All e.s.d.'s (except the e.s.d. in the dihedral angle between two l.s. planes)
are estimated using the full covariance matrix. The cell e.s.d.'s are taken
into account individually in the estimation of e.s.d.'s in distances, angles
and torsion angles; correlations between e.s.d.'s in cell parameters are only
used when they are defined by crystal symmetry. An approximate (isotropic)
treatment of cell e.s.d.'s is used for estimating e.s.d.'s 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 N5 . 1.3742(12) ?
    O1 N6 . 1.3929(12) ?
    N1 C2 . 1.3342(12) ?
    N1 C1 . 1.3616(12) ?
    N2 C3 . 1.3236(13) ?
    N2 C2 . 1.3497(12) ?
    N3 N4 . 1.3583(11) ?
    N3 C5 . 1.3643(12) ?
    N3 C2 . 1.3912(12) ?
    N4 C1 . 1.3449(12) ?
    N5 C12 . 1.3106(13) ?
    N6 C13 . 1.3095(13) ?
    C1 C6 . 1.4693(13) ?
    C3 C4 . 1.4160(14) ?
    C3 H3A . 0.9500 ?
    C4 C5 . 1.3702(13) ?
    C4 H4A . 0.9500 ?
    C5 C12 . 1.4678(13) ?
    C6 C11 . 1.3968(14) ?
    C6 C7 . 1.3979(13) ?
    C7 C8 . 1.3914(14) ?
    C7 H7A . 0.9500 ?
    C8 C9 . 1.3910(16) ?
    C8 H8A . 0.9500 ?
    C9 C10 . 1.3931(16) ?
    C9 H9A . 0.9500 ?
    C10 C11 . 1.3909(14) ?
    C10 H10A . 0.9500 ?
    C11 H11A . 0.9500 ?
    C12 C13 . 1.4373(13) ?
    C13 C14 . 1.4914(14) ?
    C14 H14A . 0.9800 ?
    C14 H14B . 0.9800 ?
    C14 H14C . 0.9800 ?
loop_
    _geom_contact_atom_site_label_1
    _geom_contact_atom_site_label_2
    _geom_contact_distance
    _geom_contact_site_symmetry_1
    _geom_contact_site_symmetry_2
    _geom_contact_publ_flag
    Cg1 Cg1 3.456(2) . 3_755 y
    Cg2 Cg3 3.540(2) . 3_756 y
    Cg1 Cg3 3.591(2) . 3_756 y
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
    N5 O1 N6 . . 110.69(8) ?
    C2 N1 C1 . . 103.20(8) ?
    C3 N2 C2 . . 115.36(9) ?
    N4 N3 C5 . . 127.33(8) ?
    N4 N3 C2 . . 110.41(8) ?
    C5 N3 C2 . . 122.26(8) ?
    C1 N4 N3 . . 101.55(7) ?
    C12 N5 O1 . . 105.55(8) ?
    C13 N6 O1 . . 106.41(8) ?
    N4 C1 N1 . . 116.01(8) ?
    N4 C1 C6 . . 121.32(8) ?
    N1 C1 C6 . . 122.66(8) ?
    N1 C2 N2 . . 128.91(9) ?
    N1 C2 N3 . . 108.82(8) ?
    N2 C2 N3 . . 122.27(9) ?
    N2 C3 C4 . . 124.87(9) ?
    N2 C3 H3A . . 117.6 ?
    C4 C3 H3A . . 117.6 ?
    C5 C4 C3 . . 119.05(9) ?
    C5 C4 H4A . . 120.5 ?
    C3 C4 H4A . . 120.5 ?
    N3 C5 C4 . . 116.17(9) ?
    N3 C5 C12 . . 119.63(8) ?
    C4 C5 C12 . . 124.20(9) ?
    C11 C6 C7 . . 119.61(9) ?
    C11 C6 C1 . . 121.11(9) ?
    C7 C6 C1 . . 119.25(9) ?
    C8 C7 C6 . . 120.31(9) ?
    C8 C7 H7A . . 119.8 ?
    C6 C7 H7A . . 119.8 ?
    C7 C8 C9 . . 119.96(9) ?
    C7 C8 H8A . . 120.0 ?
    C9 C8 H8A . . 120.0 ?
    C10 C9 C8 . . 119.82(10) ?
    C10 C9 H9A . . 120.1 ?
    C8 C9 H9A . . 120.1 ?
    C11 C10 C9 . . 120.48(10) ?
    C11 C10 H10A . . 119.8 ?
    C9 C10 H10A . . 119.8 ?
    C10 C11 C6 . . 119.80(10) ?
    C10 C11 H11A . . 120.1 ?
    C6 C11 H11A . . 120.1 ?
    N5 C12 C13 . . 109.75(9) ?
    N5 C12 C5 . . 118.64(9) ?
    C13 C12 C5 . . 131.49(9) ?
    N6 C13 C12 . . 107.61(9) ?
    N6 C13 C14 . . 122.10(9) ?
    C12 C13 C14 . . 130.27(9) ?
    C13 C14 H14A . . 109.5 ?
    C13 C14 H14B . . 109.5 ?
    H14A C14 H14B . . 109.5 ?
    C13 C14 H14C . . 109.5 ?
    H14A C14 H14C . . 109.5 ?
    H14B C14 H14C . . 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
    C5 N3 N4 C1 . . . . -179.38(9) ?
    C2 N3 N4 C1 . . . . 1.14(9) ?
    N6 O1 N5 C12 . . . . 0.26(12) ?
    N5 O1 N6 C13 . . . . -0.33(12) ?
    N3 N4 C1 N1 . . . . -0.77(10) ?
    N3 N4 C1 C6 . . . . 177.98(8) ?
    C2 N1 C1 N4 . . . . 0.08(11) ?
    C2 N1 C1 C6 . . . . -178.65(8) ?
    C1 N1 C2 N2 . . . . -178.95(10) ?
    C1 N1 C2 N3 . . . . 0.65(10) ?
    C3 N2 C2 N1 . . . . 179.64(9) ?
    C3 N2 C2 N3 . . . . 0.09(14) ?
    N4 N3 C2 N1 . . . . -1.19(10) ?
    C5 N3 C2 N1 . . . . 179.29(8) ?
    N4 N3 C2 N2 . . . . 178.44(8) ?
    C5 N3 C2 N2 . . . . -1.08(14) ?
    C2 N2 C3 C4 . . . . 0.60(15) ?
    N2 C3 C4 C5 . . . . -0.33(15) ?
    N4 N3 C5 C4 . . . . -178.14(9) ?
    C2 N3 C5 C4 . . . . 1.30(13) ?
    N4 N3 C5 C12 . . . . 1.79(14) ?
    C2 N3 C5 C12 . . . . -178.78(8) ?
    C3 C4 C5 N3 . . . . -0.63(13) ?
    C3 C4 C5 C12 . . . . 179.46(9) ?
    N4 C1 C6 C11 . . . . -5.31(14) ?
    N1 C1 C6 C11 . . . . 173.36(9) ?
    N4 C1 C6 C7 . . . . 176.72(9) ?
    N1 C1 C6 C7 . . . . -4.61(13) ?
    C11 C6 C7 C8 . . . . -0.83(14) ?
    C1 C6 C7 C8 . . . . 177.17(9) ?
    C6 C7 C8 C9 . . . . 0.02(15) ?
    C7 C8 C9 C10 . . . . 0.85(17) ?
    C8 C9 C10 C11 . . . . -0.91(18) ?
    C9 C10 C11 C6 . . . . 0.09(17) ?
    C7 C6 C11 C10 . . . . 0.77(15) ?
    C1 C6 C11 C10 . . . . -177.19(10) ?
    O1 N5 C12 C13 . . . . -0.09(12) ?
    O1 N5 C12 C5 . . . . -176.58(9) ?
    N3 C5 C12 N5 . . . . -136.53(10) ?
    C4 C5 C12 N5 . . . . 43.38(14) ?
    N3 C5 C12 C13 . . . . 47.89(15) ?
    C4 C5 C12 C13 . . . . -132.19(11) ?
    O1 N6 C13 C12 . . . . 0.26(11) ?
    O1 N6 C13 C14 . . . . 178.61(9) ?
    N5 C12 C13 N6 . . . . -0.11(12) ?
    C5 C12 C13 N6 . . . . 175.77(10) ?
    N5 C12 C13 C14 . . . . -178.28(10) ?
    C5 C12 C13 C14 . . . . -2.40(18) ?
data_New_Global_Publ_Block
_journal_date_recd_electronic     2013-09-27
_journal_date_accepted     2013-10-09
_journal_name_full     'Acta Crystallographica, Section E'
_journal_year     2013
_journal_volume     69
_journal_issue     11
_journal_page_first     o1648
_journal_page_last     o1649
_journal_paper_category     QO
_journal_paper_doi     10.1107/S1600536813027700
_journal_coeditor_code     CV5430
_publ_contact_author_name     'Suponitsky Kyrill'
_publ_contact_author_address
;
A. N. Nesmeyanov Institute of Organoelement Compounds,
Russian Academy of Sciences, 28 Vavilova St., 119991 Moscow, Russia
;
_publ_contact_author_email     'kirshik@yahoo.com'
_publ_contact_author_fax     ?
_publ_contact_author_phone     ?
_publ_section_title
;
3-Methyl-4-(2-phenyl-1,2,4-triazolo[1,5-a]pyrimidin-7-yl)furazan
;
loop_
    _publ_author_name
    _publ_author_footnote
    _publ_author_address
    'Suponitsky, Kyrill Yu.' .
;
A. N. Nesmeyanov Institute of Organoelement Compounds,
Russian Academy of Sciences, 28 Vavilova St, 119991 Moscow,
Russian Federation
;
    'Chernyshev, Victor M.' .
;
South-Russia State Technical University, 346428 Novocherkassk,
Russian Federation
;
    'Palysaeva, Nadezhda V.' .
;
N. D. Zelinsky Institute of Organic Chemistry, Russian Academy of Sciences
47 Leninsky Prosp., 119991 Moscow,
Russian Federation
;
    'Sheremetev, Aleksei B.' .
;
N. D. Zelinsky Institute of Organic Chemistry, Russian Academy of Sciences
47 Leninsky Prosp., 119991 Moscow,
Russian Federation
;
