Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536807056632/hk2370sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S1600536807056632/hk2370Isup2.hkl |
CCDC reference: 674085
Key indicators
- Single-crystal X-ray study
- T = 298 K
- Mean (C-C) = 0.009 Å
- R factor = 0.085
- wR factor = 0.154
- Data-to-parameter ratio = 17.2
checkCIF/PLATON results
No syntax errors found
Alert level C PLAT230_ALERT_2_C Hirshfeld Test Diff for P - O1 .. 5.57 su PLAT241_ALERT_2_C Check High Ueq as Compared to Neighbors for C4 PLAT242_ALERT_2_C Check Low Ueq as Compared to Neighbors for O3 PLAT242_ALERT_2_C Check Low Ueq as Compared to Neighbors for C17 PLAT250_ALERT_2_C Large U3/U1 Ratio for Average U(i,j) Tensor .... 2.12 PLAT322_ALERT_2_C Check Hybridisation of S in Main Residue . ? PLAT340_ALERT_3_C Low Bond Precision on C-C Bonds (x 1000) Ang ... 10 PLAT360_ALERT_2_C Short C(sp3)-C(sp3) Bond C1 - C2 ... 1.39 Ang. PLAT360_ALERT_2_C Short C(sp3)-C(sp3) Bond C3 - C4 ... 1.42 Ang.
Alert level G PLAT793_ALERT_1_G Check the Absolute Configuration of C5 = ... R
0 ALERT level A = In general: serious problem 0 ALERT level B = Potentially serious problem 9 ALERT level C = Check and explain 1 ALERT level G = General alerts; check 1 ALERT type 1 CIF construction/syntax error, inconsistent or missing data 8 ALERT type 2 Indicator that the structure model may be wrong or deficient 1 ALERT type 3 Indicator that the structure quality may be low 0 ALERT type 4 Improvement, methodology, query or suggestion 0 ALERT type 5 Informative message, check
For related literature, see: Nakagawa et al. (1996); Wang et al. (1999). For bond-length data, see: Allen et al. (1987).
For the preparation of the title compound, N-benzylidene-5-(2,4-dichlorophenyl) -1,3,4-thiadiazol-2-amine (2 mmol) and diethyl phosphite (5 mmol) were added in a flask (25 ml) and reacted in an oil bath (363 K) for 6 h. After cooling and filtering, crude compound (I) was obtained, and recrystallized from ethanol. Crystals of (I) suitable for X-ray analysis were obtained by slow evaporation of an acetone solution.
H atoms were positioned geometrically, with N—H = 0.86 Å (for NH) and C—H = 0.98, 0.97 and 0.96 Å for methine, methylene and methyl H atoms, respectively, and constrained to ride on their parent atoms, with Uiso(H) = xUeq(C,N), where x = 1.5 for methyl H and x = 1.2 for all other H atoms.
Data collection: CAD-4 Software (Enraf–Nonius, 1989); cell refinement: CAD-4 Software (Enraf–Nonius, 1989); data reduction: XCAD4 (Harms & Wocadlo, 1995); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: SHELXTL (Siemens, 1996); software used to prepare material for publication: SHELXTL (Siemens, 1996).
C19H20Cl2N3O3PS | F(000) = 976 |
Mr = 472.31 | Dx = 1.428 Mg m−3 |
Monoclinic, P21/n | Melting point = 453–454 K |
Hall symbol: -P 2yn | Mo Kα radiation, λ = 0.71073 Å |
a = 8.4870 (17) Å | Cell parameters from 25 reflections |
b = 16.530 (3) Å | θ = 10–12° |
c = 15.703 (3) Å | µ = 0.49 mm−1 |
β = 94.47 (3)° | T = 298 K |
V = 2196.3 (7) Å3 | Needle, colorless |
Z = 4 | 0.40 × 0.10 × 0.10 mm |
Enraf–Nonius CAD-4 diffractometer | 3145 reflections with I > 2σ(I) |
Radiation source: fine-focus sealed tube | Rint = 0.052 |
Graphite monochromator | θmax = 26.0°, θmin = 1.8° |
ω/2θ scans | h = −10→10 |
Absorption correction: ψ scan (North et al., 1968) | k = 0→20 |
Tmin = 0.828, Tmax = 0.953 | l = 0→19 |
4609 measured reflections | 3 standard reflections every 200 reflections |
4312 independent reflections | intensity decay: none |
Refinement on F2 | Secondary atom site location: difference Fourier map |
Least-squares matrix: full | Hydrogen site location: inferred from neighbouring sites |
R[F2 > 2σ(F2)] = 0.085 | H-atom parameters constrained |
wR(F2) = 0.154 | w = 1/[σ2(Fo2) + (0.1265P)2 + 1.3578P] where P = (Fo2 + 2Fc2)/3 |
S = 1.17 | (Δ/σ)max < 0.001 |
4312 reflections | Δρmax = 0.31 e Å−3 |
250 parameters | Δρmin = −0.70 e Å−3 |
Primary atom site location: structure-invariant direct methods |
C19H20Cl2N3O3PS | V = 2196.3 (7) Å3 |
Mr = 472.31 | Z = 4 |
Monoclinic, P21/n | Mo Kα radiation |
a = 8.4870 (17) Å | µ = 0.49 mm−1 |
b = 16.530 (3) Å | T = 298 K |
c = 15.703 (3) Å | 0.40 × 0.10 × 0.10 mm |
β = 94.47 (3)° |
Enraf–Nonius CAD-4 diffractometer | 3145 reflections with I > 2σ(I) |
Absorption correction: ψ scan (North et al., 1968) | Rint = 0.052 |
Tmin = 0.828, Tmax = 0.953 | 3 standard reflections every 200 reflections |
4609 measured reflections | intensity decay: none |
4312 independent reflections |
R[F2 > 2σ(F2)] = 0.085 | 250 parameters |
wR(F2) = 0.154 | H-atom parameters constrained |
S = 1.17 | Δρmax = 0.31 e Å−3 |
4312 reflections | Δρmin = −0.70 e Å−3 |
Geometry. 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. |
Refinement. 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. |
x | y | z | Uiso*/Ueq | ||
Cl1 | 0.3460 (3) | 0.37335 (12) | 0.14352 (10) | 0.1114 (7) | |
Cl2 | 0.3666 (2) | 0.44309 (12) | −0.18670 (9) | 0.1133 (8) | |
S | 0.1558 (2) | 0.48605 (11) | 0.25006 (9) | 0.0806 (6) | |
P | 0.0393 (2) | 0.65490 (13) | 0.52266 (9) | 0.0760 (6) | |
O1 | 0.2180 (6) | 0.6788 (3) | 0.5237 (2) | 0.1143 (17) | |
O2 | 0.0005 (6) | 0.5841 (3) | 0.5707 (2) | 0.1010 (16) | |
O3 | −0.0427 (5) | 0.7339 (3) | 0.5529 (2) | 0.0810 (13) | |
N1 | 0.0476 (5) | 0.5763 (3) | 0.3769 (2) | 0.0743 (15) | |
H1A | 0.0697 | 0.5357 | 0.4099 | 0.089* | |
N2 | 0.0586 (6) | 0.6318 (3) | 0.2402 (3) | 0.0777 (15) | |
N3 | 0.1044 (6) | 0.6122 (3) | 0.1607 (3) | 0.0800 (16) | |
C1 | 0.3610 (7) | 0.6550 (4) | 0.6493 (4) | 0.100 | |
H1B | 0.4266 | 0.6728 | 0.6983 | 0.150* | |
H1C | 0.4184 | 0.6170 | 0.6174 | 0.150* | |
H1D | 0.2679 | 0.6294 | 0.6678 | 0.150* | |
C2 | 0.3175 (8) | 0.7211 (4) | 0.5980 (4) | 0.104 | |
H2C | 0.4090 | 0.7483 | 0.5780 | 0.125* | |
H2D | 0.2548 | 0.7596 | 0.6275 | 0.125* | |
C3 | −0.1313 (9) | 0.7382 (5) | 0.6870 (5) | 0.139 (3) | |
H3B | −0.2156 | 0.7363 | 0.7243 | 0.209* | |
H3C | −0.0786 | 0.7895 | 0.6929 | 0.209* | |
H3D | −0.0574 | 0.6956 | 0.7017 | 0.209* | |
C4 | −0.1941 (9) | 0.7282 (5) | 0.6014 (4) | 0.126 (3) | |
H4A | −0.2685 | 0.7708 | 0.5842 | 0.151* | |
H4B | −0.2454 | 0.6760 | 0.5928 | 0.151* | |
C5 | −0.0214 (6) | 0.6487 (4) | 0.4094 (3) | 0.0625 (16) | |
H5A | 0.0225 | 0.6954 | 0.3810 | 0.075* | |
C6 | −0.1952 (8) | 0.6534 (5) | 0.3975 (3) | 0.0728 (17) | |
C7 | −0.2645 (8) | 0.7291 (5) | 0.3791 (4) | 0.094 (2) | |
H7A | −0.2045 | 0.7752 | 0.3711 | 0.112* | |
C8 | −0.4350 (10) | 0.7307 (6) | 0.3735 (4) | 0.114 (3) | |
H8A | −0.4841 | 0.7805 | 0.3632 | 0.137* | |
C9 | −0.5298 (10) | 0.6650 (6) | 0.3820 (4) | 0.107 (2) | |
H9A | −0.6394 | 0.6689 | 0.3761 | 0.128* | |
C10 | −0.4547 (10) | 0.5930 (5) | 0.3999 (4) | 0.105 (2) | |
H10A | −0.5146 | 0.5470 | 0.4085 | 0.126* | |
C11 | −0.2943 (8) | 0.5873 (5) | 0.4053 (4) | 0.091 (2) | |
H11A | −0.2487 | 0.5366 | 0.4147 | 0.109* | |
C12 | 0.0776 (6) | 0.5735 (4) | 0.2916 (3) | 0.0647 (16) | |
C13 | 0.1598 (7) | 0.5399 (4) | 0.1552 (3) | 0.0660 (17) | |
C14 | 0.2134 (6) | 0.5107 (4) | 0.0727 (3) | 0.0646 (16) | |
C15 | 0.1763 (7) | 0.5587 (4) | 0.0007 (3) | 0.0771 (18) | |
H15A | 0.1172 | 0.6056 | 0.0058 | 0.092* | |
C16 | 0.2262 (7) | 0.5374 (4) | −0.0786 (3) | 0.0709 (17) | |
H16A | 0.2031 | 0.5702 | −0.1261 | 0.085* | |
C17 | 0.3105 (7) | 0.4667 (4) | −0.0856 (3) | 0.0694 (17) | |
C18 | 0.3452 (7) | 0.4183 (4) | −0.0185 (3) | 0.0785 (19) | |
H18A | 0.4053 | 0.3718 | −0.0239 | 0.094* | |
C19 | 0.2892 (7) | 0.4390 (4) | 0.0592 (3) | 0.0715 (18) |
U11 | U22 | U33 | U12 | U13 | U23 | |
Cl1 | 0.180 (2) | 0.0953 (15) | 0.0658 (11) | 0.0132 (14) | 0.0529 (11) | −0.0004 (10) |
Cl2 | 0.1685 (18) | 0.1257 (18) | 0.0526 (9) | −0.0267 (15) | 0.0524 (10) | −0.0308 (10) |
S | 0.1088 (13) | 0.0911 (14) | 0.0463 (8) | −0.0013 (11) | 0.0348 (8) | −0.0076 (9) |
P | 0.0906 (14) | 0.0975 (16) | 0.0420 (9) | −0.0043 (12) | 0.0253 (8) | −0.0148 (10) |
O1 | 0.119 (4) | 0.125 (5) | 0.061 (3) | −0.016 (4) | 0.025 (2) | −0.030 (3) |
O2 | 0.168 (5) | 0.085 (4) | 0.056 (2) | 0.003 (3) | 0.043 (3) | −0.002 (2) |
O3 | 0.094 (3) | 0.086 (4) | 0.056 (2) | 0.043 (3) | −0.043 (2) | −0.006 (2) |
N1 | 0.096 (4) | 0.093 (4) | 0.038 (2) | 0.009 (3) | 0.028 (2) | −0.005 (3) |
N2 | 0.101 (4) | 0.087 (4) | 0.051 (3) | −0.009 (3) | 0.039 (3) | 0.000 (3) |
N3 | 0.115 (4) | 0.080 (4) | 0.050 (3) | −0.004 (3) | 0.039 (3) | −0.009 (3) |
C1 | 0.100 (4) | 0.107 (3) | 0.100 (3) | −0.001 (2) | 0.008 (2) | 0.000 (3) |
C2 | 0.104 (4) | 0.108 (4) | 0.104 (4) | −0.002 (2) | 0.007 (3) | 0.000 (3) |
C3 | 0.149 (6) | 0.151 (7) | 0.118 (5) | 0.009 (6) | 0.015 (5) | −0.007 (5) |
C4 | 0.156 (6) | 0.129 (6) | 0.099 (5) | 0.037 (5) | 0.040 (4) | −0.006 (5) |
C5 | 0.065 (4) | 0.076 (4) | 0.050 (3) | −0.001 (3) | 0.028 (3) | −0.009 (3) |
C6 | 0.081 (4) | 0.097 (5) | 0.042 (3) | −0.004 (4) | 0.018 (3) | −0.012 (3) |
C7 | 0.090 (4) | 0.112 (5) | 0.080 (4) | 0.009 (4) | 0.013 (4) | −0.008 (4) |
C8 | 0.109 (5) | 0.130 (6) | 0.104 (5) | 0.019 (5) | 0.014 (5) | −0.015 (5) |
C9 | 0.105 (5) | 0.144 (6) | 0.074 (4) | −0.005 (4) | 0.022 (4) | −0.005 (5) |
C10 | 0.104 (5) | 0.134 (6) | 0.079 (4) | −0.025 (5) | 0.029 (4) | −0.010 (5) |
C11 | 0.096 (4) | 0.112 (5) | 0.069 (4) | −0.018 (4) | 0.032 (4) | −0.015 (4) |
C12 | 0.061 (4) | 0.084 (4) | 0.052 (3) | −0.003 (3) | 0.027 (3) | −0.019 (3) |
C13 | 0.075 (4) | 0.081 (4) | 0.043 (3) | −0.010 (4) | 0.020 (3) | −0.005 (3) |
C14 | 0.066 (4) | 0.084 (4) | 0.046 (3) | −0.022 (3) | 0.017 (3) | −0.007 (3) |
C15 | 0.100 (4) | 0.088 (5) | 0.045 (3) | 0.000 (4) | 0.019 (3) | −0.003 (3) |
C16 | 0.085 (4) | 0.091 (5) | 0.038 (3) | −0.019 (4) | 0.014 (3) | −0.008 (3) |
C17 | 0.089 (4) | 0.075 (5) | 0.047 (3) | −0.021 (4) | 0.016 (3) | −0.016 (3) |
C18 | 0.096 (4) | 0.090 (5) | 0.053 (3) | −0.014 (4) | 0.030 (3) | −0.018 (3) |
C19 | 0.087 (4) | 0.082 (4) | 0.050 (3) | −0.012 (4) | 0.031 (3) | −0.003 (3) |
Cl1—C19 | 1.751 (6) | C4—H4A | 0.9700 |
Cl2—C17 | 1.737 (5) | C4—H4B | 0.9700 |
S—C13 | 1.737 (6) | C5—C6 | 1.475 (7) |
S—C12 | 1.738 (6) | C5—H5A | 0.9800 |
P—O2 | 1.444 (4) | C6—C11 | 1.391 (8) |
P—O1 | 1.567 (5) | C6—C7 | 1.402 (9) |
P—O3 | 1.570 (4) | C7—C8 | 1.443 (9) |
P—C5 | 1.815 (5) | C7—H7A | 0.9300 |
O1—C2 | 1.552 (7) | C8—C9 | 1.365 (10) |
O3—C4 | 1.547 (7) | C8—H8A | 0.9300 |
N1—C12 | 1.383 (6) | C9—C10 | 1.368 (10) |
N1—C5 | 1.443 (6) | C9—H9A | 0.9300 |
N1—H1A | 0.8600 | C10—C11 | 1.361 (9) |
N2—C12 | 1.260 (7) | C10—H10A | 0.9300 |
N2—N3 | 1.376 (5) | C11—H11A | 0.9300 |
N3—C13 | 1.289 (7) | C13—C14 | 1.487 (6) |
C1—C2 | 1.391 (7) | C14—C19 | 1.372 (8) |
C1—H1B | 0.9600 | C14—C15 | 1.397 (7) |
C1—H1C | 0.9600 | C15—C16 | 1.392 (7) |
C1—H1D | 0.9600 | C15—H15A | 0.9300 |
C2—H2C | 0.9700 | C16—C17 | 1.379 (8) |
C2—H2D | 0.9700 | C16—H16A | 0.9300 |
C3—C4 | 1.416 (8) | C17—C18 | 1.338 (8) |
C3—H3B | 0.9600 | C18—C19 | 1.387 (7) |
C3—H3C | 0.9600 | C18—H18A | 0.9300 |
C3—H3D | 0.9600 | ||
C13—S—C12 | 86.0 (3) | P—C5—H5A | 108.2 |
O2—P—O1 | 117.3 (3) | C11—C6—C7 | 118.2 (7) |
O2—P—O3 | 113.1 (2) | C11—C6—C5 | 123.5 (7) |
O1—P—O3 | 103.8 (3) | C7—C6—C5 | 118.2 (7) |
O2—P—C5 | 114.0 (3) | C6—C7—C8 | 115.6 (8) |
O1—P—C5 | 103.0 (2) | C6—C7—H7A | 122.2 |
O3—P—C5 | 104.2 (3) | C8—C7—H7A | 122.2 |
C2—O1—P | 126.2 (4) | C9—C8—C7 | 125.1 (9) |
C4—O3—P | 120.2 (4) | C9—C8—H8A | 117.4 |
C12—N1—C5 | 118.8 (5) | C7—C8—H8A | 117.4 |
C12—N1—H1A | 120.6 | C8—C9—C10 | 116.3 (8) |
C5—N1—H1A | 120.6 | C8—C9—H9A | 121.8 |
C12—N2—N3 | 111.7 (5) | C10—C9—H9A | 121.8 |
C13—N3—N2 | 114.1 (5) | C11—C10—C9 | 121.4 (8) |
C2—C1—H1B | 109.5 | C11—C10—H10A | 119.3 |
C2—C1—H1C | 109.5 | C9—C10—H10A | 119.3 |
H1B—C1—H1C | 109.5 | C10—C11—C6 | 123.2 (8) |
C2—C1—H1D | 109.5 | C10—C11—H11A | 118.4 |
H1B—C1—H1D | 109.5 | C6—C11—H11A | 118.4 |
H1C—C1—H1D | 109.5 | N2—C12—N1 | 124.8 (6) |
C1—C2—O1 | 100.7 (6) | N2—C12—S | 115.4 (4) |
C1—C2—H2C | 111.6 | N1—C12—S | 119.7 (5) |
O1—C2—H2C | 111.6 | N3—C13—C14 | 119.7 (5) |
C1—C2—H2D | 111.6 | N3—C13—S | 112.7 (4) |
O1—C2—H2D | 111.6 | C14—C13—S | 127.5 (5) |
H2C—C2—H2D | 109.4 | C19—C14—C15 | 116.3 (5) |
C4—C3—H3B | 109.5 | C19—C14—C13 | 126.4 (6) |
C4—C3—H3C | 109.5 | C15—C14—C13 | 117.2 (6) |
H3B—C3—H3C | 109.5 | C16—C15—C14 | 121.0 (6) |
C4—C3—H3D | 109.5 | C16—C15—H15A | 119.5 |
H3B—C3—H3D | 109.5 | C14—C15—H15A | 119.5 |
H3C—C3—H3D | 109.5 | C17—C16—C15 | 118.8 (6) |
C3—C4—O3 | 101.2 (6) | C17—C16—H16A | 120.6 |
C3—C4—H4A | 111.5 | C15—C16—H16A | 120.6 |
O3—C4—H4A | 111.5 | C18—C17—C16 | 121.9 (6) |
C3—C4—H4B | 111.5 | C18—C17—Cl2 | 121.7 (6) |
O3—C4—H4B | 111.5 | C16—C17—Cl2 | 116.4 (5) |
H4A—C4—H4B | 109.3 | C17—C18—C19 | 118.4 (6) |
N1—C5—C6 | 115.4 (5) | C17—C18—H18A | 120.8 |
N1—C5—P | 107.6 (4) | C19—C18—H18A | 120.8 |
C6—C5—P | 109.0 (3) | C14—C19—C18 | 123.2 (6) |
N1—C5—H5A | 108.2 | C14—C19—Cl1 | 121.5 (4) |
C6—C5—H5A | 108.2 | C18—C19—Cl1 | 114.8 (5) |
D—H···A | D—H | H···A | D···A | D—H···A |
N1—H1A···O2i | 0.86 | 2.09 | 2.815 (7) | 141 |
C4—H4A···N3ii | 0.97 | 2.56 | 3.321 (11) | 134 |
C15—H15A···N3 | 0.93 | 2.45 | 2.783 (7) | 101 |
Symmetry codes: (i) −x, −y+1, −z+1; (ii) x−1/2, −y+3/2, z+1/2. |
Experimental details
Crystal data | |
Chemical formula | C19H20Cl2N3O3PS |
Mr | 472.31 |
Crystal system, space group | Monoclinic, P21/n |
Temperature (K) | 298 |
a, b, c (Å) | 8.4870 (17), 16.530 (3), 15.703 (3) |
β (°) | 94.47 (3) |
V (Å3) | 2196.3 (7) |
Z | 4 |
Radiation type | Mo Kα |
µ (mm−1) | 0.49 |
Crystal size (mm) | 0.40 × 0.10 × 0.10 |
Data collection | |
Diffractometer | Enraf–Nonius CAD-4 diffractometer |
Absorption correction | ψ scan (North et al., 1968) |
Tmin, Tmax | 0.828, 0.953 |
No. of measured, independent and observed [I > 2σ(I)] reflections | 4609, 4312, 3145 |
Rint | 0.052 |
(sin θ/λ)max (Å−1) | 0.617 |
Refinement | |
R[F2 > 2σ(F2)], wR(F2), S | 0.085, 0.154, 1.17 |
No. of reflections | 4312 |
No. of parameters | 250 |
No. of restraints | ? |
H-atom treatment | H-atom parameters constrained |
Δρmax, Δρmin (e Å−3) | 0.31, −0.70 |
Computer programs: CAD-4 Software (Enraf–Nonius, 1989), XCAD4 (Harms & Wocadlo, 1995), SHELXS97 (Sheldrick, 1997), SHELXL97 (Sheldrick, 1997), SHELXTL (Siemens, 1996).
D—H···A | D—H | H···A | D···A | D—H···A |
N1—H1A···O2i | 0.86 | 2.09 | 2.815 (7) | 141 |
C4—H4A···N3ii | 0.97 | 2.56 | 3.321 (11) | 134 |
C15—H15A···N3 | 0.93 | 2.45 | 2.783 (7) | 101 |
Symmetry codes: (i) −x, −y+1, −z+1; (ii) x−1/2, −y+3/2, z+1/2. |
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1,3,4-Thiadiazole derivatives represent an interesting class of compounds possessing broad spectrum biological activities (Nakagawa et al., 1996; Wang et al., 1999). These compounds are known to exhibit diverse biological effects, such as insecticidal and fungicidal activities (Wang et al., 1999).
In the molecule of (I) (Fig. 1), the bond lengths and angles are within normal ranges (Allen et al., 1987). Rings A (C6—C11), B (S/N2/N3/C12/C13) and C (C14—C19) are, of course, planar and the dihedral angles between them are A/B = 74.19 (3)°, A/C = 75.91 (3)° and B/C = 10.69 (3)°. The intramolecular C—H···N hydrogen bond (Table 1) results in the formation of a nearly planar five-membered ring; D (N3/C13—C15/H7A), which is oriented with respect to the adjacent rings B and C, at dihedral angles of B/D = 10.93 (2)° and C/D = 5.632 (3)°.
In the crystal structure, intermolecular N—H···O and C—H···N hydrogen bonds (Table 1, Fig. 2)) link the molecules, in which they seem to be effective in the stabilization of the structure.