organic compounds
6-Amino-3,4-dimethyl-1,2,4-triazin-1-ium 2-anilinobenzoate–3-amino-5,6-dimethyl-1,2,4-triazine (1/1)
aDepartment of Chemistry, Government Arts College (Autonomous), Thanthonimalai, Karur 639 005, Tamil Nadu, India, bDepartment of Chemistry, Government Arts College, Thiruchirappalli 620 022, Tamilnadu, India, and cSchool of Physics, Universiti Sains Malaysia, 11800 USM, Penang, Malaysia
*Correspondence e-mail: manavaibala@gmail.com
In the title molecular salt, C5H9N4+·C13H10NO2−·C5H8N4, the consists of a 6-amino-3,4-dimethyl-1,2,4-triazin-1-ium cation, a 2-anilinobenzoate anion and a neutral 3-amino-5,6-dimethyl-1,2,4-triazine molecule. The typical intramolecular N⋯H—O hydrogen bond is observed in the 2-anilinobenzoate anion. In the crystal, the protonated N atom and the 3-amino group are hydrogen bonded to the carboxylate oxygen atoms via a pair of N—H⋯O hydrogen bonds, forming an R22 (8) ring motif. These motifs are further linked with adjacent neutral 3-amino-5,6-dimethyl-1,2,4-triazine molecules by N—H⋯O and N—H⋯N hydrogen bonds to produce centrosymmetric six-membered units, enclosing R22(8) and R34(9) ring motifs. They are reinforced by a C—H⋯N hydrogen bond and stack up the b-axis direction.
Keywords: crystal structure; 1,2,4-triazine; 1,2,4-triazinium; benzoate; hydrogen bonding.
CCDC reference: 1554175
Structure description
; Kumar et al., 2014). 1,2,4-Triazines and their analogues occupy a important position in medicinal chemistry as a result of their pharmacological activities (Abdel-Monem, 2010). Drugs containing a 1,2,4-triazine ring are present in natural and many synthetic products, for example azaribine and lamotrigine, that have important biological activities. The of 3-amino-5,6-dimethyl-1,2,4-triazine (Wu et al., 2012) and 3-amino-5,6-dimethyl-1,2,4-triazin-2-ium nitrate (Bel Haj Salah et al., 2013) have been reported. In order to study potential hydrogen-bonding interactions, the determination of the title molecular salt was carried out.
play a role in the design of new drugs and materials (García-Valverde & Torroba, 2005The structure of the title molecular salt is illustrated in Fig. 1. It is composed of a 6-amino-3,4-dimethyl-1,2,4-triazinium cation, a 2-anilinobenzoate anion and one neutral 3-amino-5,6-dimethyl-1,2,4-triazine molecule. Proton transfer from one of the carboxylate oxygen atoms (O1) to atom N2A of the cation results in widening of the C1A—N2A—N1A angle of the triazinium ring to 123.40 (13)°, compared to the corresponding angle of 117.9 (3)° in neutral 3-amino-5,6-dimethyl-1,2,4-triazine (Wu et al., 2012), and that of the neutral 3-amino-5,6-dimethyl-1,2,4-triazine molecule present in the title molecular salt, where angle N1B—N2B—C1B is 117.46 (12) °. The dihedral angle between the rings in the anion is 44.55 (11)°. There is a typical intramolecular hydrogen bond N5—H1N5⋯O1 between the NH and carboxylate group of the 2-anilinobenzoate anion, forming an S(6) ring motif (Fig. 1).
In the crystal, the protonated N atom, N2A, and the 3-amino group (N3A) are hydrogen bonded to the carboxylate oxygen atoms (O1 and O2) via a pair of N2A—H1N2⋯O1i and N3A—H1NA⋯O2i hydrogen bonds, forming an R22 (8) ring motif (Table 1 and Fig. 2). These motifs are further linked with adjacent neutral 3-amino-5,6-dimethyl-1,2,4-triazine molecules by N3B—H2NB⋯O2, N3A—H2NA⋯N1Bii and N3B—H1NB⋯N2Biii hydrogen bonds to produce a complementary DDAA (D = donor, A = acceptor) hydrogen-bonded array (Table 1 and Fig. 2). These centrosymmetric six-membered units enclose R22(8) and R43(9) ring motifs, are reinforced by a C—H⋯N hydrogen bond, and stack up the b-axis direction (Table 1, Fig. 3).
Synthesis and crystallization
A hot methanol solution (20 ml) of 3-amino-5,6-dimethyl-1,2,4-triazine (62 mg, Aldrich) and 2-anilinobenzoic acid (100 mg, Merk) were mixed and warmed over a heating magnetic stirrer hotplate for a few minutes. The resulting solution was allowed to cool slowly at room temperature and green plate-like crystals of the title compound appeared after a few days.
Refinement
Crystal data, data collection and structure .
details are summarized in Table 2
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Structural data
CCDC reference: 1554175
https://doi.org/10.1107/S241431461700829X/su4153sup1.cif
contains datablock I. DOI:Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S241431461700829X/su4153Isup2.hkl
Supporting information file. DOI: https://doi.org/10.1107/S241431461700829X/su4153Isup3.cml
Data collection: APEX2 (Bruker, 2009); cell
SAINT (Bruker, 2009); data reduction: SAINT (Bruker, 2009); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL2013 (Sheldrick, 2015); molecular graphics: PLATON (Spek, 2009) and Mercury (Macrae et al., 2008); software used to prepare material for publication: SHELXL2013 (Sheldrick, 2015) and PLATON (Spek, 2009).C5H9N4+·C13H10NO2−·C5H8N4 | Z = 2 |
Mr = 461.53 | F(000) = 488 |
Triclinic, P1 | Dx = 1.305 Mg m−3 |
a = 7.5018 (3) Å | Mo Kα radiation, λ = 0.71073 Å |
b = 7.6661 (3) Å | Cell parameters from 2760 reflections |
c = 21.4332 (9) Å | θ = 1.0–29.0° |
α = 93.743 (1)° | µ = 0.09 mm−1 |
β = 94.776 (1)° | T = 293 K |
γ = 106.197 (1)° | Plate, green |
V = 1174.52 (8) Å3 | 0.61 × 0.49 × 0.18 mm |
Bruker SMART APEXII CCD area-detector diffractometer | 4622 independent reflections |
Radiation source: fine-focus sealed tube | 3468 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.049 |
φ and ω scans | θmax = 26.0°, θmin = 1.9° |
Absorption correction: multi-scan (SADABS; Bruker, 2009) | h = −9→9 |
Tmin = 0.947, Tmax = 0.984 | k = −9→9 |
35176 measured reflections | l = −26→26 |
Refinement on F2 | Primary atom site location: structure-invariant direct methods |
Least-squares matrix: full | Secondary atom site location: difference Fourier map |
R[F2 > 2σ(F2)] = 0.045 | Hydrogen site location: mixed |
wR(F2) = 0.133 | H atoms treated by a mixture of independent and constrained refinement |
S = 1.04 | w = 1/[σ2(Fo2) + (0.0628P)2 + 0.222P] where P = (Fo2 + 2Fc2)/3 |
4622 reflections | (Δ/σ)max = 0.001 |
335 parameters | Δρmax = 0.17 e Å−3 |
0 restraints | Δρmin = −0.15 e Å−3 |
Geometry. 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. |
x | y | z | Uiso*/Ueq | ||
O1 | −0.06951 (14) | 0.41109 (18) | 0.27879 (6) | 0.0645 (4) | |
O2 | 0.04258 (14) | 0.29631 (16) | 0.19905 (5) | 0.0577 (3) | |
N5 | 0.1635 (2) | 0.6138 (2) | 0.37067 (7) | 0.0626 (4) | |
H5N | 0.052 (3) | 0.560 (3) | 0.3544 (9) | 0.067 (6)* | |
C6 | 0.06398 (19) | 0.4021 (2) | 0.24742 (7) | 0.0426 (3) | |
C7 | 0.25436 (19) | 0.52475 (19) | 0.27027 (7) | 0.0406 (3) | |
C8 | 0.3935 (2) | 0.5411 (2) | 0.23022 (8) | 0.0484 (4) | |
H8 | 0.3652 | 0.4748 | 0.1910 | 0.058* | |
C9 | 0.5720 (2) | 0.6525 (2) | 0.24700 (9) | 0.0596 (5) | |
H9 | 0.6636 | 0.6598 | 0.2198 | 0.071* | |
C10 | 0.6127 (2) | 0.7530 (3) | 0.30453 (10) | 0.0638 (5) | |
H10 | 0.7325 | 0.8299 | 0.3160 | 0.077* | |
C11 | 0.4795 (2) | 0.7416 (2) | 0.34506 (9) | 0.0602 (5) | |
H11 | 0.5100 | 0.8125 | 0.3834 | 0.072* | |
C12 | 0.2980 (2) | 0.6253 (2) | 0.33008 (7) | 0.0472 (4) | |
C13 | 0.1844 (3) | 0.6725 (2) | 0.43498 (8) | 0.0601 (5) | |
C14 | 0.3339 (3) | 0.6662 (4) | 0.47597 (10) | 0.0913 (7) | |
H14 | 0.4305 | 0.6270 | 0.4610 | 0.110* | |
C15 | 0.3400 (4) | 0.7182 (5) | 0.53918 (12) | 0.1181 (10) | |
H15 | 0.4412 | 0.7134 | 0.5665 | 0.142* | |
C16 | 0.2015 (5) | 0.7762 (4) | 0.56239 (12) | 0.1152 (10) | |
H16 | 0.2079 | 0.8122 | 0.6050 | 0.138* | |
C17 | 0.0526 (5) | 0.7806 (4) | 0.52206 (13) | 0.1038 (9) | |
H17 | −0.0440 | 0.8187 | 0.5375 | 0.125* | |
C18 | 0.0435 (3) | 0.7293 (3) | 0.45877 (10) | 0.0760 (6) | |
H18 | −0.0590 | 0.7332 | 0.4319 | 0.091* | |
N1A | 0.48051 (18) | 0.19326 (19) | 0.29896 (6) | 0.0516 (3) | |
N2A | 0.59717 (17) | 0.18820 (18) | 0.25468 (6) | 0.0474 (3) | |
H2AA | 0.727 (3) | 0.276 (3) | 0.2642 (9) | 0.072 (5)* | |
N3A | 0.67322 (19) | 0.0737 (2) | 0.16252 (7) | 0.0519 (4) | |
H3AA | 0.796 (3) | 0.147 (2) | 0.1719 (8) | 0.059 (5)* | |
H3AB | 0.633 (3) | 0.001 (3) | 0.1252 (9) | 0.063 (5)* | |
N4A | 0.36953 (16) | −0.02836 (18) | 0.18697 (6) | 0.0479 (3) | |
C1A | 0.54793 (19) | 0.0788 (2) | 0.20174 (7) | 0.0425 (3) | |
C2A | 0.2532 (2) | −0.0255 (2) | 0.22879 (8) | 0.0478 (4) | |
C3A | 0.3111 (2) | 0.0859 (2) | 0.28723 (8) | 0.0500 (4) | |
C4A | 0.1833 (3) | 0.0886 (3) | 0.33697 (10) | 0.0702 (5) | |
H4AA | 0.1544 | −0.0262 | 0.3550 | 0.105* | |
H4AC | 0.0703 | 0.1087 | 0.3187 | 0.105* | |
H4AB | 0.2433 | 0.1850 | 0.3692 | 0.105* | |
C5A | 0.0571 (2) | −0.1422 (3) | 0.21318 (10) | 0.0635 (5) | |
H5AB | 0.0453 | −0.2096 | 0.1730 | 0.095* | |
H5AA | −0.0256 | −0.0666 | 0.2118 | 0.095* | |
H5AC | 0.0253 | −0.2257 | 0.2447 | 0.095* | |
N1B | 0.41507 (18) | 0.15155 (19) | −0.03886 (6) | 0.0511 (3) | |
N2B | 0.25699 (17) | 0.11190 (18) | −0.01023 (6) | 0.0485 (3) | |
N3B | 0.1073 (2) | 0.1583 (2) | 0.07556 (7) | 0.0583 (4) | |
H3BA | 0.003 (3) | 0.080 (3) | 0.0562 (9) | 0.063 (5)* | |
H3BB | 0.112 (3) | 0.218 (3) | 0.1170 (10) | 0.067 (5)* | |
N4B | 0.41980 (17) | 0.30830 (18) | 0.07997 (6) | 0.0496 (3) | |
C1B | 0.2648 (2) | 0.1919 (2) | 0.04733 (7) | 0.0442 (4) | |
C2B | 0.5721 (2) | 0.3445 (2) | 0.05112 (7) | 0.0458 (4) | |
C3B | 0.5703 (2) | 0.2650 (2) | −0.01015 (8) | 0.0462 (4) | |
C4B | 0.7392 (2) | 0.3046 (3) | −0.04550 (9) | 0.0610 (5) | |
H4BC | 0.7099 | 0.2325 | −0.0853 | 0.092* | |
H4BB | 0.8390 | 0.2750 | −0.0216 | 0.092* | |
H4BA | 0.7769 | 0.4317 | −0.0523 | 0.092* | |
C5B | 0.7458 (2) | 0.4714 (3) | 0.08573 (9) | 0.0647 (5) | |
H5BA | 0.7891 | 0.5753 | 0.0625 | 0.097* | |
H5BC | 0.8403 | 0.4093 | 0.0904 | 0.097* | |
H5BB | 0.7197 | 0.5111 | 0.1265 | 0.097* |
U11 | U22 | U33 | U12 | U13 | U23 | |
O1 | 0.0336 (6) | 0.0799 (8) | 0.0667 (7) | −0.0027 (5) | 0.0164 (5) | −0.0197 (6) |
O2 | 0.0390 (6) | 0.0671 (7) | 0.0558 (7) | −0.0016 (5) | 0.0124 (5) | −0.0122 (6) |
N5 | 0.0453 (8) | 0.0807 (11) | 0.0498 (8) | 0.0014 (7) | 0.0105 (7) | −0.0138 (7) |
C6 | 0.0343 (7) | 0.0445 (8) | 0.0463 (8) | 0.0055 (6) | 0.0089 (6) | 0.0049 (7) |
C7 | 0.0318 (7) | 0.0410 (8) | 0.0479 (8) | 0.0072 (6) | 0.0080 (6) | 0.0061 (6) |
C8 | 0.0389 (8) | 0.0501 (9) | 0.0542 (9) | 0.0073 (7) | 0.0124 (7) | 0.0035 (7) |
C9 | 0.0355 (8) | 0.0656 (11) | 0.0727 (12) | 0.0035 (7) | 0.0179 (8) | 0.0042 (9) |
C10 | 0.0344 (8) | 0.0642 (11) | 0.0804 (13) | −0.0047 (7) | 0.0055 (8) | 0.0002 (9) |
C11 | 0.0458 (9) | 0.0623 (11) | 0.0613 (10) | 0.0005 (8) | 0.0029 (8) | −0.0065 (8) |
C12 | 0.0391 (8) | 0.0489 (9) | 0.0502 (9) | 0.0073 (6) | 0.0071 (7) | 0.0014 (7) |
C13 | 0.0631 (11) | 0.0580 (10) | 0.0490 (9) | 0.0003 (8) | 0.0144 (8) | −0.0030 (8) |
C14 | 0.0760 (14) | 0.127 (2) | 0.0610 (13) | 0.0152 (13) | 0.0033 (11) | −0.0005 (13) |
C15 | 0.106 (2) | 0.161 (3) | 0.0582 (14) | −0.0041 (19) | −0.0043 (14) | 0.0025 (16) |
C16 | 0.148 (3) | 0.118 (2) | 0.0536 (14) | −0.005 (2) | 0.0274 (17) | −0.0105 (14) |
C17 | 0.146 (3) | 0.0996 (19) | 0.0746 (16) | 0.0367 (18) | 0.0564 (18) | 0.0055 (14) |
C18 | 0.0891 (15) | 0.0833 (14) | 0.0600 (11) | 0.0244 (12) | 0.0320 (11) | 0.0092 (10) |
N1A | 0.0436 (7) | 0.0580 (8) | 0.0523 (8) | 0.0101 (6) | 0.0131 (6) | 0.0076 (6) |
N2A | 0.0345 (7) | 0.0522 (7) | 0.0510 (8) | 0.0033 (6) | 0.0099 (6) | 0.0052 (6) |
N3A | 0.0349 (7) | 0.0623 (9) | 0.0525 (8) | 0.0031 (6) | 0.0103 (6) | 0.0020 (7) |
N4A | 0.0324 (6) | 0.0512 (8) | 0.0563 (8) | 0.0050 (5) | 0.0059 (6) | 0.0062 (6) |
C1A | 0.0316 (7) | 0.0459 (8) | 0.0485 (8) | 0.0065 (6) | 0.0072 (6) | 0.0107 (7) |
C2A | 0.0339 (8) | 0.0473 (9) | 0.0637 (10) | 0.0092 (6) | 0.0119 (7) | 0.0174 (8) |
C3A | 0.0405 (8) | 0.0532 (9) | 0.0587 (10) | 0.0121 (7) | 0.0151 (7) | 0.0166 (8) |
C4A | 0.0587 (11) | 0.0821 (13) | 0.0730 (12) | 0.0164 (10) | 0.0305 (10) | 0.0170 (10) |
C5A | 0.0335 (8) | 0.0637 (11) | 0.0876 (13) | 0.0016 (7) | 0.0115 (8) | 0.0130 (10) |
N1B | 0.0418 (7) | 0.0583 (8) | 0.0508 (8) | 0.0079 (6) | 0.0137 (6) | 0.0046 (6) |
N2B | 0.0366 (7) | 0.0562 (8) | 0.0480 (7) | 0.0047 (6) | 0.0097 (6) | 0.0033 (6) |
N3B | 0.0374 (8) | 0.0774 (10) | 0.0518 (9) | 0.0030 (7) | 0.0126 (6) | −0.0048 (8) |
N4B | 0.0406 (7) | 0.0559 (8) | 0.0493 (7) | 0.0082 (6) | 0.0069 (6) | 0.0039 (6) |
C1B | 0.0363 (8) | 0.0500 (8) | 0.0460 (8) | 0.0103 (6) | 0.0073 (6) | 0.0080 (7) |
C2B | 0.0378 (8) | 0.0454 (8) | 0.0524 (9) | 0.0076 (6) | 0.0062 (7) | 0.0088 (7) |
C3B | 0.0371 (8) | 0.0460 (8) | 0.0554 (9) | 0.0089 (6) | 0.0111 (7) | 0.0090 (7) |
C4B | 0.0455 (9) | 0.0643 (11) | 0.0695 (11) | 0.0064 (8) | 0.0199 (8) | 0.0037 (9) |
C5B | 0.0454 (9) | 0.0691 (11) | 0.0681 (11) | −0.0008 (8) | 0.0042 (8) | 0.0018 (9) |
O1—C6 | 1.2665 (17) | N3A—C1A | 1.3189 (19) |
O2—C6 | 1.2445 (18) | N3A—H3AA | 0.933 (19) |
N5—C12 | 1.375 (2) | N3A—H3AB | 0.92 (2) |
N5—C13 | 1.404 (2) | N4A—C2A | 1.3056 (19) |
N5—H5N | 0.85 (2) | N4A—C1A | 1.3595 (18) |
C6—C7 | 1.496 (2) | C2A—C3A | 1.431 (2) |
C7—C8 | 1.390 (2) | C2A—C5A | 1.490 (2) |
C7—C12 | 1.416 (2) | C3A—C4A | 1.494 (2) |
C8—C9 | 1.376 (2) | C4A—H4AA | 0.9600 |
C8—H8 | 0.9300 | C4A—H4AC | 0.9600 |
C9—C10 | 1.375 (3) | C4A—H4AB | 0.9600 |
C9—H9 | 0.9300 | C5A—H5AB | 0.9600 |
C10—C11 | 1.366 (2) | C5A—H5AA | 0.9600 |
C10—H10 | 0.9300 | C5A—H5AC | 0.9600 |
C11—C12 | 1.402 (2) | N1B—C3B | 1.318 (2) |
C11—H11 | 0.9300 | N1B—N2B | 1.3490 (17) |
C13—C18 | 1.373 (3) | N2B—C1B | 1.331 (2) |
C13—C14 | 1.380 (3) | N3B—C1B | 1.3412 (19) |
C14—C15 | 1.380 (3) | N3B—H3BA | 0.89 (2) |
C14—H14 | 0.9300 | N3B—H3BB | 0.97 (2) |
C15—C16 | 1.356 (4) | N4B—C2B | 1.3142 (19) |
C15—H15 | 0.9300 | N4B—C1B | 1.3572 (19) |
C16—C17 | 1.364 (4) | C2B—C3B | 1.409 (2) |
C16—H16 | 0.9300 | C2B—C5B | 1.494 (2) |
C17—C18 | 1.378 (3) | C3B—C4B | 1.499 (2) |
C17—H17 | 0.9300 | C4B—H4BC | 0.9600 |
C18—H18 | 0.9300 | C4B—H4BB | 0.9600 |
N1A—C3A | 1.301 (2) | C4B—H4BA | 0.9600 |
N1A—N2A | 1.3493 (17) | C5B—H5BA | 0.9600 |
N2A—C1A | 1.327 (2) | C5B—H5BC | 0.9600 |
N2A—H2AA | 1.02 (2) | C5B—H5BB | 0.9600 |
C12—N5—C13 | 129.15 (16) | C2A—N4A—C1A | 116.78 (14) |
C12—N5—H5N | 114.8 (13) | N3A—C1A—N2A | 119.79 (13) |
C13—N5—H5N | 116.0 (13) | N3A—C1A—N4A | 119.16 (14) |
O2—C6—O1 | 122.75 (13) | N2A—C1A—N4A | 121.05 (13) |
O2—C6—C7 | 119.44 (12) | N4A—C2A—C3A | 121.44 (13) |
O1—C6—C7 | 117.81 (13) | N4A—C2A—C5A | 117.34 (15) |
C8—C7—C12 | 118.97 (14) | C3A—C2A—C5A | 121.22 (14) |
C8—C7—C6 | 117.89 (13) | N1A—C3A—C2A | 120.46 (14) |
C12—C7—C6 | 123.13 (13) | N1A—C3A—C4A | 116.60 (16) |
C9—C8—C7 | 121.86 (16) | C2A—C3A—C4A | 122.94 (15) |
C9—C8—H8 | 119.1 | C3A—C4A—H4AA | 109.5 |
C7—C8—H8 | 119.1 | C3A—C4A—H4AC | 109.5 |
C10—C9—C8 | 118.98 (15) | H4AA—C4A—H4AC | 109.5 |
C10—C9—H9 | 120.5 | C3A—C4A—H4AB | 109.5 |
C8—C9—H9 | 120.5 | H4AA—C4A—H4AB | 109.5 |
C11—C10—C9 | 120.92 (15) | H4AC—C4A—H4AB | 109.5 |
C11—C10—H10 | 119.5 | C2A—C5A—H5AB | 109.5 |
C9—C10—H10 | 119.5 | C2A—C5A—H5AA | 109.5 |
C10—C11—C12 | 121.42 (16) | H5AB—C5A—H5AA | 109.5 |
C10—C11—H11 | 119.3 | C2A—C5A—H5AC | 109.5 |
C12—C11—H11 | 119.3 | H5AB—C5A—H5AC | 109.5 |
N5—C12—C11 | 121.59 (15) | H5AA—C5A—H5AC | 109.5 |
N5—C12—C7 | 120.56 (14) | C3B—N1B—N2B | 120.50 (13) |
C11—C12—C7 | 117.79 (14) | C1B—N2B—N1B | 117.46 (12) |
C18—C13—C14 | 118.46 (18) | C1B—N3B—H3BA | 119.5 (11) |
C18—C13—N5 | 118.06 (18) | C1B—N3B—H3BB | 118.4 (11) |
C14—C13—N5 | 123.37 (18) | H3BA—N3B—H3BB | 122.0 (16) |
C15—C14—C13 | 119.9 (3) | C2B—N4B—C1B | 116.13 (13) |
C15—C14—H14 | 120.0 | N2B—C1B—N3B | 118.09 (14) |
C13—C14—H14 | 120.0 | N2B—C1B—N4B | 125.25 (13) |
C16—C15—C14 | 121.5 (3) | N3B—C1B—N4B | 116.65 (14) |
C16—C15—H15 | 119.3 | N4B—C2B—C3B | 120.74 (14) |
C14—C15—H15 | 119.3 | N4B—C2B—C5B | 117.67 (14) |
C15—C16—C17 | 118.7 (2) | C3B—C2B—C5B | 121.59 (14) |
C15—C16—H16 | 120.6 | N1B—C3B—C2B | 119.91 (13) |
C17—C16—H16 | 120.6 | N1B—C3B—C4B | 117.31 (15) |
C16—C17—C18 | 120.8 (3) | C2B—C3B—C4B | 122.79 (14) |
C16—C17—H17 | 119.6 | C3B—C4B—H4BC | 109.5 |
C18—C17—H17 | 119.6 | C3B—C4B—H4BB | 109.5 |
C13—C18—C17 | 120.6 (2) | H4BC—C4B—H4BB | 109.5 |
C13—C18—H18 | 119.7 | C3B—C4B—H4BA | 109.5 |
C17—C18—H18 | 119.7 | H4BC—C4B—H4BA | 109.5 |
C3A—N1A—N2A | 116.69 (14) | H4BB—C4B—H4BA | 109.5 |
C1A—N2A—N1A | 123.40 (13) | C2B—C5B—H5BA | 109.5 |
C1A—N2A—H2AA | 121.3 (11) | C2B—C5B—H5BC | 109.5 |
N1A—N2A—H2AA | 115.3 (11) | H5BA—C5B—H5BC | 109.5 |
C1A—N3A—H3AA | 120.2 (11) | C2B—C5B—H5BB | 109.5 |
C1A—N3A—H3AB | 117.7 (11) | H5BA—C5B—H5BB | 109.5 |
H3AA—N3A—H3AB | 122.0 (16) | H5BC—C5B—H5BB | 109.5 |
O2—C6—C7—C8 | 12.1 (2) | C3A—N1A—N2A—C1A | −1.2 (2) |
O1—C6—C7—C8 | −168.01 (14) | N1A—N2A—C1A—N3A | −175.83 (13) |
O2—C6—C7—C12 | −168.55 (15) | N1A—N2A—C1A—N4A | 4.4 (2) |
O1—C6—C7—C12 | 11.4 (2) | C2A—N4A—C1A—N3A | 176.54 (14) |
C12—C7—C8—C9 | −0.2 (2) | C2A—N4A—C1A—N2A | −3.7 (2) |
C6—C7—C8—C9 | 179.15 (15) | C1A—N4A—C2A—C3A | 0.2 (2) |
C7—C8—C9—C10 | −1.2 (3) | C1A—N4A—C2A—C5A | 179.96 (14) |
C8—C9—C10—C11 | 0.8 (3) | N2A—N1A—C3A—C2A | −2.3 (2) |
C9—C10—C11—C12 | 1.1 (3) | N2A—N1A—C3A—C4A | 178.65 (14) |
C13—N5—C12—C11 | −16.2 (3) | N4A—C2A—C3A—N1A | 2.9 (2) |
C13—N5—C12—C7 | 166.56 (17) | C5A—C2A—C3A—N1A | −176.87 (15) |
C10—C11—C12—N5 | −179.81 (17) | N4A—C2A—C3A—C4A | −178.16 (15) |
C10—C11—C12—C7 | −2.5 (3) | C5A—C2A—C3A—C4A | 2.1 (2) |
C8—C7—C12—N5 | 179.39 (15) | C3B—N1B—N2B—C1B | 0.2 (2) |
C6—C7—C12—N5 | 0.0 (2) | N1B—N2B—C1B—N3B | 177.90 (14) |
C8—C7—C12—C11 | 2.0 (2) | N1B—N2B—C1B—N4B | −1.0 (2) |
C6—C7—C12—C11 | −177.32 (14) | C2B—N4B—C1B—N2B | 0.9 (2) |
C12—N5—C13—C18 | 148.89 (19) | C2B—N4B—C1B—N3B | −178.02 (14) |
C12—N5—C13—C14 | −34.9 (3) | C1B—N4B—C2B—C3B | 0.0 (2) |
C18—C13—C14—C15 | −0.7 (4) | C1B—N4B—C2B—C5B | −179.67 (15) |
N5—C13—C14—C15 | −176.9 (2) | N2B—N1B—C3B—C2B | 0.6 (2) |
C13—C14—C15—C16 | −0.1 (5) | N2B—N1B—C3B—C4B | −178.99 (13) |
C14—C15—C16—C17 | 0.8 (5) | N4B—C2B—C3B—N1B | −0.7 (2) |
C15—C16—C17—C18 | −0.8 (5) | C5B—C2B—C3B—N1B | 178.95 (15) |
C14—C13—C18—C17 | 0.7 (3) | N4B—C2B—C3B—C4B | 178.86 (15) |
N5—C13—C18—C17 | 177.1 (2) | C5B—C2B—C3B—C4B | −1.5 (2) |
C16—C17—C18—C13 | 0.0 (4) |
D—H···A | D—H | H···A | D···A | D—H···A |
N5—H5N···O1 | 0.85 (2) | 1.92 (2) | 2.619 (2) | 138 (2) |
N2A—H2AA···O1i | 1.02 (2) | 1.58 (2) | 2.593 (2) | 179 (2) |
N3A—H3AA···O2i | 0.93 (2) | 1.90 (2) | 2.834 (2) | 175 (2) |
N3A—H3AB···N1Bii | 0.92 (2) | 2.07 (2) | 2.986 (2) | 172 (2) |
N3B—H3BA···N2Biii | 0.89 (2) | 2.20 (2) | 3.089 (2) | 179 (2) |
N3B—H3BB···O2 | 0.97 (2) | 1.98 (2) | 2.915 (2) | 163 (2) |
C4B—H4BC···N4Aii | 0.96 | 2.52 | 3.483 (2) | 177 |
Symmetry codes: (i) x+1, y, z; (ii) −x+1, −y, −z; (iii) −x, −y, −z. |
Acknowledgements
KB thanks the Department of Science and Technology (DST-SERB), New Delhi, India, for financial support (grant No. SB/ FT/CS-058/2013), RS thanks the Department of Science and Technology (DST), New Delhi, India, for financial support in the form of an INSPIRE fellowship (INSPIRE code No. IF131050).
References
Abdel-Monem, W. R. (2010). E-J. Chem. 1, 168–172. CAS Google Scholar
Bel Haj Salah, S., Mrad, M. L., Ferretti, V., Lefebvre, F. & Ben Nasr, C. (2013). Acta Cryst. E69, o844. CSD CrossRef IUCr Journals Google Scholar
Bruker (2009). APEX2, SAINT, and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
García-Valverde, M. & Torroba, T. (2005). Molecules, 10, 318–320. Google Scholar
Kumar, R., Sirohi, T. S., Singh, H., Yadav, R., Roy, R. K., Chaudhary, A. & Pandeya, S. N. (2014). Mini Rev. Med. Chem. 14, 168–207. CrossRef CAS PubMed Google Scholar
Macrae, C. F., Bruno, I. J., Chisholm, J. A., Edgington, P. R., McCabe, P., Pidcock, E., Rodriguez-Monge, L., Taylor, R., van de Streek, J. & Wood, P. A. (2008). J. Appl. Cryst. 41, 466–470. Web of Science CSD CrossRef CAS IUCr Journals Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar
Sheldrick, G. M. (2015). Acta Cryst. C71, 3–8. Web of Science CrossRef IUCr Journals Google Scholar
Spek, A. L. (2009). Acta Cryst. D65, 148–155. Web of Science CrossRef CAS IUCr Journals Google Scholar
Wu, M.-H., Qiu, Q.-M., Gao, S., Jin, Q.-H. & Zhang, C.-L. (2012). Acta Cryst. E68, o39. Web of Science CSD CrossRef IUCr Journals Google Scholar
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