# Electronic Supplementary Material (ESI) for RSC Advances
# This journal is © The Royal Society of Chemistry 2012


data_global
_journal_name_full               'RSC Advances'
_journal_coden_cambridge         1500
#TrackingRef '15a.CIF'

_publ_contact_author             
;
Shishkina S.V.
Institute for Single Crystals
60 Lenina ave.
Kharkiv, 61072
Ukraine
;
_publ_contact_author_phone       '380 57 341 02 58'
_publ_contact_author_fax         '380 57 341 02 73'
_publ_contact_author_email       sveta@xray.isc.kharkov.com

_publ_contact_letter             
;
Paper containing this structure has been
submitted to Chemical Communications.
;

_iucr_compatibility_tag          ACTA95

_publ_section_title              
;
Dotting the i's in three-component Biginelli-like condensation using
3-amino-1,2,4-triazole as 1,3-binucleophile.
;

_publ_section_exptl_prep         
;
?
;
loop_
_publ_author_name
'Sedash, Yuriy'
'Gorobets, Nikolay'
'Chebanov, Valentin'
'Konovalova, Irina'
'Shishkin, Oleg'
'Desenko, Sergey'

data_experimental
_database_code_depnum_ccdc_archive 'CCDC 857098'
#TrackingRef '15a.CIF'

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C14 H16 N4 O3'
_chemical_formula_sum            'C14 H16 N4 O3'
_chemical_formula_weight         288.31

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'

_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_H-M   P2(1)2(1)2(1)

loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'x+1/2, -y+1/2, -z'
'-x, y+1/2, -z+1/2'

_cell_length_a                   5.6370(4)
_cell_length_b                   10.2308(7)
_cell_length_c                   24.765(2)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_volume                     1428.3
_cell_formula_units_Z            4
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    3751
_cell_measurement_theta_min      3.2
_cell_measurement_theta_max      30.9

_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.20
_exptl_crystal_size_mid          0.10
_exptl_crystal_size_min          0.10
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.341
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             608
_exptl_absorpt_coefficient_mu    0.097
_exptl_absorpt_correction_type   none
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?

_exptl_special_details           
;
?
;

_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'Enhance (Mo) X-ray Source'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  Xcalibur"3
_diffrn_measurement_method       \w-scans
_diffrn_detector_area_resol_mean 16.1827
_diffrn_standards_number         2
_diffrn_standards_interval_count 50
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            9265
_diffrn_reflns_av_R_equivalents  0.0539
_diffrn_reflns_av_sigmaI/netI    0.0352
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_h_max       5
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_l_min       -29
_diffrn_reflns_limit_l_max       29
_diffrn_reflns_theta_min         3.17
_diffrn_reflns_theta_max         25.00
_reflns_number_total             1480
_reflns_number_gt                1190
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       
;
CrysAlis CCD, Oxford Diffraction Ltd.,
Version 1.171.27p5 beta (release 01-04-2005 CrysAlis171 .NET)
(compiled Apr 1 2005,17:53:34)
;
_computing_cell_refinement       
;
CrysAlis RED, Oxford Diffraction Ltd.,
Version 1.171.27p5 beta (release 01-04-2005 CrysAlis171 .NET)
(compiled Apr 1 2005,17:53:34)
;
_computing_data_reduction        
;
CrysAlis RED, Oxford Diffraction Ltd.,
Version 1.171.27p5 beta (release 01-04-2005 CrysAlis171 .NET)
(compiled Apr 1 2005,17:53:34)
;
_computing_structure_solution    'SHELXTL (Sheldrick, 1998)'
_computing_structure_refinement  'SHELXTL (Sheldrick, 1998)'
_computing_molecular_graphics    'XP (Siemens, 1998)'
_computing_publication_material  'SHELXTL (Sheldrick, 1998)'

_refine_special_details          
;
Refinement of F^2^ against ALL reflections. The weighted R-factor wR and
goodness of fit S are based on F^2^, conventional R-factors R are based
on F, with F set to zero for negative F^2^. The threshold expression of
F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is
not relevant to the choice of reflections for refinement. R-factors based
on F^2^ are statistically about twice as large as those based on F, and R-
factors based on ALL data will be even larger.
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[\s^2^(Fo^2^)+(0.0447P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   difmap
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   4(2)
_refine_ls_number_reflns         1480
_refine_ls_number_parameters     194
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0617
_refine_ls_R_factor_gt           0.0443
_refine_ls_wR_factor_ref         0.0957
_refine_ls_wR_factor_gt          0.0909
_refine_ls_goodness_of_fit_ref   1.156
_refine_ls_restrained_S_all      1.156
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
N1 N -0.0150(5) 0.4561(3) 0.71544(9) 0.0491(7) Uani 1 1 d . . .
N2 N 0.1706(6) 0.6515(2) 0.71383(9) 0.0485(7) Uani 1 1 d . . .
N3 N 0.1907(5) 0.5934(2) 0.76422(9) 0.0393(6) Uani 1 1 d . . .
N4 N 0.0728(5) 0.4027(3) 0.80688(10) 0.0526(8) Uani 1 1 d . . .
H4N H 0.0156 0.3250 0.8041 0.063 Uiso 1 1 calc R . .
O1 O 0.1658(5) 0.73579(19) 0.83852(8) 0.0484(6) Uani 1 1 d . . .
H1O H 0.1272 0.7974 0.8192 0.073 Uiso 1 1 calc R . .
O2 O 0.3393(5) 0.5970(3) 0.94320(9) 0.0630(7) Uani 1 1 d . . .
O3 O 0.6749(4) 0.6429(2) 0.89909(9) 0.0565(6) Uani 1 1 d . . .
C1 C 0.0484(6) 0.5637(3) 0.68773(12) 0.0492(9) Uani 1 1 d . . .
H1 H 0.0070 0.5749 0.6517 0.048(9) Uiso 1 1 calc R . .
C2 C 0.0779(6) 0.4801(3) 0.76395(12) 0.0383(7) Uani 1 1 d . . .
C3 C 0.3169(6) 0.6531(3) 0.81000(11) 0.0396(7) Uani 1 1 d . . .
C4 C 0.3759(5) 0.5392(3) 0.84926(11) 0.0376(7) Uani 1 1 d . . .
H4 H 0.5062 0.4878 0.8339 0.045 Uiso 1 1 calc R . .
C5 C 0.1638(6) 0.4483(3) 0.85895(11) 0.0397(7) Uani 1 1 d . . .
H5 H 0.0385 0.4987 0.8769 0.048 Uiso 1 1 calc R . .
C6 C 0.5330(6) 0.7236(4) 0.78799(14) 0.0650(11) Uani 1 1 d . . .
H6C H 0.6175 0.7642 0.8172 0.097 Uiso 1 1 calc R . .
H6B H 0.4834 0.7892 0.7627 0.097 Uiso 1 1 calc R . .
H6A H 0.6349 0.6620 0.7702 0.097 Uiso 1 1 calc R . .
C7 C 0.2140(6) 0.3286(3) 0.89239(11) 0.0393(7) Uani 1 1 d . . .
C8 C 0.0563(7) 0.2897(3) 0.93169(12) 0.0528(9) Uani 1 1 d . . .
H8 H -0.0727 0.3429 0.9398 0.063 Uiso 1 1 calc R . .
C9 C 0.0850(8) 0.1749(4) 0.95907(13) 0.0672(11) Uani 1 1 d . . .
H9 H -0.0236 0.1510 0.9856 0.081 Uiso 1 1 calc R . .
C10 C 0.2738(8) 0.0946(4) 0.94760(15) 0.0715(12) Uani 1 1 d . . .
H10 H 0.2941 0.0164 0.9661 0.086 Uiso 1 1 calc R . .
C11 C 0.4302(7) 0.1313(4) 0.90880(15) 0.0717(12) Uani 1 1 d . . .
H11 H 0.5582 0.0773 0.9007 0.086 Uiso 1 1 calc R . .
C12 C 0.4026(6) 0.2467(3) 0.88124(13) 0.0537(9) Uani 1 1 d . . .
H12 H 0.5119 0.2700 0.8548 0.064 Uiso 1 1 calc R . .
C13 C 0.4557(6) 0.5947(3) 0.90294(12) 0.0429(8) Uani 1 1 d . . .
C14 C 0.7622(7) 0.7165(4) 0.94456(14) 0.0707(12) Uani 1 1 d . . .
H14C H 0.7148 0.6743 0.9775 0.106 Uiso 1 1 calc R . .
H14B H 0.6979 0.8033 0.9435 0.106 Uiso 1 1 calc R . .
H14A H 0.9322 0.7208 0.9430 0.106 Uiso 1 1 calc R . .

loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
N1 0.0615(19) 0.0438(15) 0.0420(14) -0.0010(13) -0.0117(15) 0.0027(15)
N2 0.0642(18) 0.0451(15) 0.0363(13) 0.0025(12) 0.0002(14) 0.0021(17)
N3 0.0449(15) 0.0392(13) 0.0338(13) 0.0019(11) -0.0042(12) -0.0034(15)
N4 0.067(2) 0.0444(14) 0.0461(15) 0.0087(13) -0.0189(15) -0.0184(16)
O1 0.0585(15) 0.0413(13) 0.0455(12) 0.0016(10) 0.0003(12) 0.0085(13)
O2 0.0572(15) 0.0908(18) 0.0409(12) -0.0056(13) 0.0031(13) -0.0129(16)
O3 0.0328(12) 0.0815(16) 0.0553(13) -0.0147(13) -0.0046(12) -0.0082(13)
C1 0.066(2) 0.045(2) 0.0373(17) 0.0012(15) -0.0107(17) 0.0069(19)
C2 0.0356(18) 0.0378(17) 0.0415(17) 0.0025(14) -0.0044(14) 0.0057(15)
C3 0.0323(16) 0.0452(17) 0.0414(16) -0.0019(15) 0.0015(15) -0.0028(17)
C4 0.0321(18) 0.0427(16) 0.0379(15) -0.0003(14) -0.0007(13) 0.0012(15)
C5 0.0326(16) 0.0426(17) 0.0438(16) -0.0008(14) 0.0004(14) 0.0019(16)
C6 0.047(2) 0.084(3) 0.064(2) 0.017(2) -0.0034(19) -0.019(2)
C7 0.0389(18) 0.0438(18) 0.0352(15) 0.0006(14) -0.0022(15) 0.0016(16)
C8 0.054(2) 0.064(2) 0.0407(17) 0.0021(17) 0.0051(16) 0.0005(19)
C9 0.080(3) 0.076(3) 0.045(2) 0.020(2) 0.0045(19) -0.010(3)
C10 0.092(3) 0.060(2) 0.063(2) 0.027(2) -0.016(2) 0.000(3)
C11 0.062(3) 0.065(2) 0.088(3) 0.019(2) -0.006(2) 0.019(2)
C12 0.045(2) 0.059(2) 0.057(2) 0.0113(18) 0.0053(17) 0.0092(19)
C13 0.0403(19) 0.0464(18) 0.0418(18) 0.0007(15) -0.0014(17) 0.0043(17)
C14 0.057(3) 0.088(3) 0.067(2) -0.018(2) -0.0133(19) -0.011(2)

_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_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
N1 C2 1.333(3) . ?
N1 C1 1.346(4) . ?
N2 C1 1.303(4) . ?
N2 N3 1.387(3) . ?
N3 C2 1.322(4) . ?
N3 C3 1.471(4) . ?
N4 C2 1.326(4) . ?
N4 C5 1.464(4) . ?
O1 C3 1.393(3) . ?
O2 C13 1.194(4) . ?
O3 C13 1.334(4) . ?
O3 C14 1.441(4) . ?
C3 C6 1.517(5) . ?
C3 C4 1.553(4) . ?
C4 C13 1.514(4) . ?
C4 C5 1.534(4) . ?
C5 C7 1.505(4) . ?
C7 C8 1.377(4) . ?
C7 C12 1.382(4) . ?
C8 C9 1.366(5) . ?
C9 C10 1.374(5) . ?
C10 C11 1.357(5) . ?
C11 C12 1.373(5) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C2 N1 C1 101.8(3) . . ?
C1 N2 N3 101.2(2) . . ?
C2 N3 N2 109.4(2) . . ?
C2 N3 C3 126.9(2) . . ?
N2 N3 C3 123.7(2) . . ?
C2 N4 C5 120.5(3) . . ?
C13 O3 C14 117.0(3) . . ?
N2 C1 N1 116.8(3) . . ?
N3 C2 N4 122.0(3) . . ?
N3 C2 N1 110.8(3) . . ?
N4 C2 N1 127.1(3) . . ?
O1 C3 N3 110.3(3) . . ?
O1 C3 C6 112.6(3) . . ?
N3 C3 C6 108.0(3) . . ?
O1 C3 C4 105.6(2) . . ?
N3 C3 C4 106.0(2) . . ?
C6 C3 C4 114.2(3) . . ?
C13 C4 C5 108.8(2) . . ?
C13 C4 C3 109.4(2) . . ?
C5 C4 C3 112.7(2) . . ?
N4 C5 C7 106.9(2) . . ?
N4 C5 C4 109.2(2) . . ?
C7 C5 C4 115.6(3) . . ?
C8 C7 C12 117.6(3) . . ?
C8 C7 C5 120.2(3) . . ?
C12 C7 C5 121.9(3) . . ?
C9 C8 C7 121.5(4) . . ?
C8 C9 C10 120.2(3) . . ?
C11 C10 C9 119.0(3) . . ?
C10 C11 C12 121.1(4) . . ?
C11 C12 C7 120.7(3) . . ?
O2 C13 O3 124.2(3) . . ?
O2 C13 C4 125.3(3) . . ?
O3 C13 C4 110.6(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
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C1 N2 N3 C2 -1.1(3) . . . . ?
C1 N2 N3 C3 179.7(3) . . . . ?
N3 N2 C1 N1 0.6(4) . . . . ?
C2 N1 C1 N2 0.1(4) . . . . ?
N2 N3 C2 N4 178.7(3) . . . . ?
C3 N3 C2 N4 -2.2(5) . . . . ?
N2 N3 C2 N1 1.3(3) . . . . ?
C3 N3 C2 N1 -179.6(3) . . . . ?
C5 N4 C2 N3 8.8(5) . . . . ?
C5 N4 C2 N1 -174.2(3) . . . . ?
C1 N1 C2 N3 -0.8(4) . . . . ?
C1 N1 C2 N4 -178.1(3) . . . . ?
C2 N3 C3 O1 -92.5(3) . . . . ?
N2 N3 C3 O1 86.6(3) . . . . ?
C2 N3 C3 C6 144.1(3) . . . . ?
N2 N3 C3 C6 -36.9(4) . . . . ?
C2 N3 C3 C4 21.4(4) . . . . ?
N2 N3 C3 C4 -159.6(3) . . . . ?
O1 C3 C4 C13 -50.3(3) . . . . ?
N3 C3 C4 C13 -167.3(2) . . . . ?
C6 C3 C4 C13 74.0(3) . . . . ?
O1 C3 C4 C5 70.8(3) . . . . ?
N3 C3 C4 C5 -46.2(3) . . . . ?
C6 C3 C4 C5 -164.9(3) . . . . ?
C2 N4 C5 C7 -160.2(3) . . . . ?
C2 N4 C5 C4 -34.4(4) . . . . ?
C13 C4 C5 N4 175.3(2) . . . . ?
C3 C4 C5 N4 53.9(3) . . . . ?
C13 C4 C5 C7 -64.1(3) . . . . ?
C3 C4 C5 C7 174.4(2) . . . . ?
N4 C5 C7 C8 -101.0(3) . . . . ?
C4 C5 C7 C8 137.2(3) . . . . ?
N4 C5 C7 C12 71.8(4) . . . . ?
C4 C5 C7 C12 -50.0(4) . . . . ?
C12 C7 C8 C9 0.4(5) . . . . ?
C5 C7 C8 C9 173.5(3) . . . . ?
C7 C8 C9 C10 -0.3(6) . . . . ?
C8 C9 C10 C11 0.0(6) . . . . ?
C9 C10 C11 C12 0.2(6) . . . . ?
C10 C11 C12 C7 0.0(6) . . . . ?
C8 C7 C12 C11 -0.3(5) . . . . ?
C5 C7 C12 C11 -173.3(3) . . . . ?
C14 O3 C13 O2 -8.1(5) . . . . ?
C14 O3 C13 C4 171.0(3) . . . . ?
C5 C4 C13 O2 -18.5(4) . . . . ?
C3 C4 C13 O2 104.9(4) . . . . ?
C5 C4 C13 O3 162.3(2) . . . . ?
C3 C4 C13 O3 -74.2(3) . . . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
N4 H4N N2 0.86 2.11 2.958(4) 168.7 4_546
O1 H1O N1 0.82 1.94 2.755(3) 170.4 4_556

_diffrn_measured_fraction_theta_max 0.986
_diffrn_reflns_theta_full        25.00
_diffrn_measured_fraction_theta_full 0.986
_refine_diff_density_max         0.155
_refine_diff_density_min         -0.147
_refine_diff_density_rms         0.036