2-Benzoyl-N-phenyl-2-(1,2,4-triazol-1-yl)­thio­acet­amide and 2-(4-methoxy­benzoyl)-N-phenyl-2-(1,2,4-triazol-1-yl)­thio­acet­amide

In the two title compounds, C₁₇H₁₄N₄OS, (I), and C₁₈H₁₆N₄O₂S, (II), the dihedral angles between the planes of the triazole and N-phenyl rings and the plane of five of the atoms that link these two rings are 63.5 (8) and 73.2 (6)° for (I), and 65.1 (1) and 72.1 (3)° for (II), respectively. There are some inter- and intramolecular interactions in the crystal structure.

S1. Comment

Recently, compounds containing the 1H-1,2,4-triazole group have attracted much interest because they exhibit some fungicidal activity and plant growth regulating activity (Xu et al., 2002), and show antibacterial activity against Puccinia recondite and roots growth regulation for cucumber (Zhao et al., 1998). In order to search for new triazole compounds with higher bioactivity, we synthesized the two title compounds, (I) and (II). Their structures are described here.

In the two title compounds, the bond lengths and angles are generally normal in the phenyl and triazole rings (Ji et al., 2002). The C—S bond lengths in the two title compounds are close to the typical C═S double-bond length. Atom C8 lies in the plane of the triazole ring, and atoms S1, C6, C7, C8 and N1 are coplane (plane p1). The dihedral angles formed by the C1–C6 phenyl and triazole rings with p1 are 63.5 (8) and 73.2 (6)° for (I), and 65.1 (1) and 72.1 (3)° for (II), respectively. These values indicate that the addition of the methoxy group to the C12–C17 phenyl ring has little influence on the molecular conformation. The C1—C6—N1—C7, N2—N4—C8—C7, N2—N4—C8—C11 and N4—C8—C11—C12 torsion angles are 25.3 (5), 88.5 (0), 147.4 (6) and 175.5 (6)° for (I), and 13.1 (0), 88.8 (8), 147.5 (9) and 171.3 (8)° for (II), respectively. The C14—C15—O2—C18 torsion angle is 173.0 (6)° for (II).

The most interesting structural features of the two complexes are the N—H···N intermolecular hydrogen bonds, and the weak C—H···Y hydrogen bonds (Y = O, N and S) intermolecular interactions (see Table 2 and Table 4). The above interactions stabilize the two structures.

S2. Experimental

The two title compounds were prepared by the reaction of A-(1,2,4-triazol-1-yl) acetophenone, phenylisothiocynate [for (I)] or phenylmethoxylisothiocynate [for (II)], and potassium hydroxide in dimethyl sulfoxide solution. Single crystals of the two title compound, suitable for X-ray measurements, were obtained by recrystallization from chloroform/ethylacetate (1:3 v/v) at room temperature.

S3. Refinement

H atoms were positioned geometrically and treated as riding on the parent C atoms, with C—H distances in the range 0.93–0.98 Å and U_iso(H) values of 1.2 and 1.5 times U_eq of the parent atoms.

Computing details

For both compounds, data collection: R-AXIS Software (Rigaku, 1997); cell refinement: R-AXIS Software; data reduction: R-AXIS Software; program(s) used to solve structure: SHELXS97 (Sheldrick, 1990a); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: SHELXTL/PC (Sheldrick, 1990b); software used to prepare material for publication: WinGX (Farrugia, 1999).

Figures

	Fig. 1. The structure of (I), showing 50% probability displacement ellipsoids and the atom-numbering scheme.
	Fig. 2. The structure of II), showing 50% probability displacement ellipsoids and the atom-numbering scheme.

(I) 2-Benzoyl-N-phenyl-2-(1,2,4-triazol-1-yl)thioacetamide

Crystal data

C17H14N4OS	F(000) = 672
Mr = 322.38	Dx = 1.411 Mg m^−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2y bc	Cell parameters from 20 reflections
a = 8.8060 (18) Å	θ = 2–11°
b = 12.097 (2) Å	µ = 0.22 mm^−1
c = 14.809 (3) Å	T = 293 K
β = 105.88 (3)°	Pillar, yellow
V = 1517.3 (6) Å^3	0.25 × 0.20 × 0.15 mm
Z = 4

Data collection

Oxford Instruments point detector diffractometer	Rint = 0.023
Radiation source: fine-focus sealed tube	θmax = 26.5°, θmin = 2.2°
Graphite monochromator	h = −10→0
θ/2θ scans	k = −15→15
5518 measured reflections	l = −17→19
3055 independent reflections	3 standard reflections every 100 reflections
2314 reflections with I > 2σ(I)	intensity decay: none

Refinement

Refinement on F^2	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F^2 > 2σ(F^2)] = 0.040	H-atom parameters constrained
wR(F^2) = 0.103	w = 1/[σ^2(Fo^2) + (0.0488P)^2 + 0.2377P] where P = (Fo^2 + 2Fc^2)/3
S = 1.09	(Δ/σ)max < 0.001
3055 reflections	Δρmax = 0.21 e Å^−3
209 parameters	Δρmin = −0.19 e Å^−3
0 restraints	Extinction correction: SHELXL97, Fc^*=kFc[1+0.001xFc^2λ^3/sin(2θ)]^-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.0133 (17)

Special details

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.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Ų)

	x	y	z	Uiso*/Ueq
S1	0.60565 (6)	0.22561 (4)	0.25140 (4)	0.04635 (18)
O1	0.95863 (16)	0.20732 (12)	0.46472 (10)	0.0479 (4)
N1	0.66517 (16)	0.01437 (12)	0.20930 (10)	0.0322 (3)
H1A	0.7376	−0.0353	0.2199	0.039*
N2	1.04861 (19)	0.14709 (14)	0.22077 (12)	0.0411 (4)
N3	1.10034 (18)	0.32874 (14)	0.25183 (12)	0.0411 (4)
N4	0.97639 (16)	0.18423 (12)	0.28582 (11)	0.0324 (3)
C1	0.3754 (2)	0.02803 (18)	0.14525 (15)	0.0438 (5)
H1B	0.3694	0.0816	0.1891	0.053*
C2	0.2401 (2)	−0.00698 (19)	0.07853 (17)	0.0524 (6)
H2B	0.1433	0.0244	0.0775	0.063*
C3	0.2468 (2)	−0.08728 (19)	0.01398 (15)	0.0487 (5)
H3B	0.1558	−0.1087	−0.0313	0.058*
C4	0.3897 (2)	−0.13574 (17)	0.01711 (14)	0.0437 (5)
H4A	0.3945	−0.1917	−0.0250	0.052*
C5	0.5255 (2)	−0.10163 (15)	0.08247 (13)	0.0368 (4)
H5A	0.6215	−0.1347	0.0844	0.044*
C6	0.5190 (2)	−0.01775 (15)	0.14557 (12)	0.0313 (4)
C7	0.70743 (19)	0.10999 (14)	0.25532 (12)	0.0302 (4)
C8	0.87825 (19)	0.10642 (14)	0.31995 (12)	0.0306 (4)
H8A	0.9198	0.0319	0.3165	0.037*
C9	1.1203 (2)	0.23689 (17)	0.20362 (15)	0.0442 (5)
H9A	1.1810	0.2375	0.1611	0.053*
C10	1.0075 (2)	0.29222 (16)	0.30207 (15)	0.0414 (5)
H10A	0.9692	0.3353	0.3429	0.050*
C11	0.8834 (2)	0.12955 (15)	0.42344 (13)	0.0344 (4)
C12	0.7988 (2)	0.05222 (16)	0.47172 (13)	0.0349 (4)
C13	0.7414 (2)	−0.05099 (17)	0.43599 (15)	0.0427 (5)
H13A	0.7513	−0.0732	0.3778	0.051*
C14	0.6701 (2)	−0.12046 (19)	0.48630 (16)	0.0495 (5)
H14A	0.6338	−0.1896	0.4624	0.059*
C15	0.6528 (2)	−0.0873 (2)	0.57203 (16)	0.0512 (6)
H15A	0.6034	−0.1337	0.6055	0.061*
C16	0.7088 (3)	0.0151 (2)	0.60830 (15)	0.0519 (6)
H16A	0.6971	0.0372	0.6661	0.062*
C17	0.7819 (2)	0.08434 (18)	0.55880 (14)	0.0432 (5)
H17A	0.8200	0.1528	0.5837	0.052*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
S1	0.0415 (3)	0.0322 (3)	0.0589 (4)	0.0088 (2)	0.0026 (2)	−0.0063 (2)
O1	0.0526 (8)	0.0462 (9)	0.0402 (8)	−0.0118 (7)	0.0050 (6)	−0.0060 (7)
N1	0.0308 (7)	0.0301 (8)	0.0350 (8)	0.0013 (6)	0.0076 (6)	−0.0032 (7)
N2	0.0494 (10)	0.0364 (9)	0.0439 (10)	0.0002 (7)	0.0234 (8)	−0.0006 (8)
N3	0.0400 (9)	0.0356 (9)	0.0492 (10)	−0.0066 (7)	0.0144 (7)	0.0014 (8)
N4	0.0316 (8)	0.0286 (8)	0.0380 (9)	−0.0009 (6)	0.0111 (6)	−0.0012 (7)
C1	0.0359 (10)	0.0476 (13)	0.0479 (12)	0.0010 (8)	0.0113 (8)	−0.0110 (10)
C2	0.0326 (10)	0.0599 (15)	0.0610 (14)	−0.0007 (9)	0.0064 (9)	−0.0085 (12)
C3	0.0423 (11)	0.0525 (14)	0.0440 (12)	−0.0116 (9)	−0.0003 (9)	−0.0019 (10)
C4	0.0529 (12)	0.0370 (11)	0.0391 (11)	−0.0088 (9)	0.0093 (9)	−0.0059 (9)
C5	0.0390 (10)	0.0313 (10)	0.0396 (11)	−0.0011 (7)	0.0101 (8)	−0.0020 (8)
C6	0.0325 (9)	0.0300 (10)	0.0305 (10)	−0.0036 (7)	0.0070 (7)	0.0005 (8)
C7	0.0310 (9)	0.0302 (10)	0.0300 (9)	−0.0008 (7)	0.0096 (7)	0.0003 (8)
C8	0.0308 (9)	0.0252 (9)	0.0361 (10)	−0.0007 (7)	0.0096 (7)	0.0010 (8)
C9	0.0466 (12)	0.0417 (12)	0.0505 (13)	−0.0005 (9)	0.0237 (9)	0.0051 (10)
C10	0.0493 (11)	0.0298 (11)	0.0487 (12)	−0.0044 (8)	0.0194 (9)	−0.0056 (9)
C11	0.0299 (9)	0.0334 (10)	0.0364 (10)	0.0035 (7)	0.0032 (7)	0.0019 (8)
C12	0.0321 (9)	0.0376 (11)	0.0325 (10)	0.0033 (7)	0.0045 (7)	0.0036 (8)
C13	0.0486 (11)	0.0411 (12)	0.0392 (11)	0.0001 (9)	0.0135 (9)	0.0010 (9)
C14	0.0552 (13)	0.0425 (12)	0.0523 (14)	−0.0061 (9)	0.0171 (10)	0.0066 (10)
C15	0.0463 (12)	0.0595 (15)	0.0506 (13)	0.0014 (10)	0.0178 (10)	0.0158 (12)
C16	0.0561 (13)	0.0642 (16)	0.0376 (12)	0.0077 (11)	0.0167 (10)	0.0075 (11)
C17	0.0442 (11)	0.0466 (13)	0.0359 (11)	0.0046 (9)	0.0058 (8)	0.0013 (9)

Geometric parameters (Å, º)

S1—C7	1.6536 (18)	C5—C6	1.392 (3)
O1—C11	1.214 (2)	C5—H5A	0.9300
N1—C7	1.342 (2)	C7—C8	1.547 (2)
N1—C6	1.425 (2)	C8—C11	1.547 (3)
N1—H1A	0.8600	C8—H8A	0.9800
N2—C9	1.314 (2)	C9—H9A	0.9300
N2—N4	1.368 (2)	C10—H10A	0.9300
N3—C10	1.322 (2)	C11—C12	1.492 (3)
N3—C9	1.359 (3)	C12—C17	1.394 (3)
N4—C10	1.343 (2)	C12—C13	1.395 (3)
N4—C8	1.457 (2)	C13—C14	1.381 (3)
C1—C6	1.380 (3)	C13—H13A	0.9300
C1—C2	1.389 (3)	C14—C15	1.380 (3)
C1—H1B	0.9300	C14—H14A	0.9300
C2—C3	1.376 (3)	C15—C16	1.385 (3)
C2—H2B	0.9300	C15—H15A	0.9300
C3—C4	1.378 (3)	C16—C17	1.381 (3)
C3—H3B	0.9300	C16—H16A	0.9300
C4—C5	1.379 (3)	C17—H17A	0.9300
C4—H4A	0.9300
C7—N1—C6	130.11 (15)	C11—C8—C7	111.56 (13)
C7—N1—H1A	114.9	N4—C8—H8A	108.0
C6—N1—H1A	114.9	C11—C8—H8A	108.0
C9—N2—N4	101.78 (16)	C7—C8—H8A	108.0
C10—N3—C9	102.29 (16)	N2—C9—N3	115.83 (18)
C10—N4—N2	109.62 (15)	N2—C9—H9A	122.1
C10—N4—C8	132.54 (15)	N3—C9—H9A	122.1
N2—N4—C8	117.75 (14)	N3—C10—N4	110.47 (17)
C6—C1—C2	119.12 (19)	N3—C10—H10A	124.8
C6—C1—H1B	120.4	N4—C10—H10A	124.8
C2—C1—H1B	120.4	O1—C11—C12	121.18 (17)
C3—C2—C1	121.11 (19)	O1—C11—C8	120.25 (17)
C3—C2—H2B	119.4	C12—C11—C8	118.54 (15)
C1—C2—H2B	119.4	C17—C12—C13	118.81 (18)
C2—C3—C4	119.42 (19)	C17—C12—C11	117.51 (17)
C2—C3—H3B	120.3	C13—C12—C11	123.64 (17)
C4—C3—H3B	120.3	C14—C13—C12	120.6 (2)
C3—C4—C5	120.29 (19)	C14—C13—H13A	119.7
C3—C4—H4A	119.9	C12—C13—H13A	119.7
C5—C4—H4A	119.9	C15—C14—C13	120.0 (2)
C4—C5—C6	120.09 (18)	C15—C14—H14A	120.0
C4—C5—H5A	120.0	C13—C14—H14A	120.0
C6—C5—H5A	120.0	C14—C15—C16	120.0 (2)
C1—C6—C5	119.87 (17)	C14—C15—H15A	120.0
C1—C6—N1	123.58 (17)	C16—C15—H15A	120.0
C5—C6—N1	116.53 (15)	C17—C16—C15	120.2 (2)
N1—C7—C8	112.09 (15)	C17—C16—H16A	119.9
N1—C7—S1	129.72 (13)	C15—C16—H16A	119.9
C8—C7—S1	118.19 (13)	C16—C17—C12	120.3 (2)
N4—C8—C11	111.55 (14)	C16—C17—H17A	119.8
N4—C8—C7	109.57 (14)	C12—C17—H17A	119.8

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1A···N3^i	0.86	2.14	2.998 (2)	174
C1—H1B···S1	0.93	2.67	3.248 (2)	120
C10—H10A···O1	0.93	2.40	2.758 (3)	103

Symmetry code: (i) −x+2, y−1/2, −z+1/2.

(II) 3-(4-methoxybenzoyl)-N-phenyl-2-(1,2,4-triazol-1-yl)thioacetamide

Crystal data

C18H16N4O2S	F(000) = 736
Mr = 352.41	Dx = 1.383 Mg m^−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2y bc	Cell parameters from 20 reflections
a = 9.806 (2) Å	θ = 2–11°
b = 11.677 (2) Å	µ = 0.21 mm^−1
c = 16.002 (5) Å	T = 293 K
β = 112.55 (2)°	Pillar, yellow
V = 1692.2 (7) Å^3	0.25 × 0.20 × 0.15 mm
Z = 4

Data collection

Oxford Instruments point detector diffractometer	Rint = 0.029
Radiation source: fine-focus sealed tube	θmax = 25.9°, θmin = 2.2°
Graphite monochromator	h = 0→12
θ/2θ scans	k = −13→13
5351 measured reflections	l = −20→18
3195 independent reflections	3 standard reflections every 100 reflections
2209 reflections with I > 2σ(I)	intensity decay: none

Refinement

Refinement on F^2	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F^2 > 2σ(F^2)] = 0.078	H-atom parameters constrained
wR(F^2) = 0.240	w = 1/[σ^2(Fo^2) + (0.1328P)^2 + 0.7232P] where P = (Fo^2 + 2Fc^2)/3
S = 1.12	(Δ/σ)max < 0.001
3195 reflections	Δρmax = 1.10 e Å^−3
227 parameters	Δρmin = −0.33 e Å^−3
0 restraints	Extinction correction: SHELXL97, Fc^*=kFc[1+0.001xFc^2λ^3/sin(2θ)]^-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.013 (4)

Special details

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.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Ų)

	x	y	z	Uiso*/Ueq
S1	0.85567 (14)	0.23060 (9)	0.25834 (9)	0.0558 (4)
O1	0.5280 (4)	0.2515 (3)	0.0498 (2)	0.0534 (8)
O2	0.8662 (4)	0.6326 (3)	−0.0805 (2)	0.0615 (9)
N1	0.8238 (4)	0.4515 (3)	0.2963 (2)	0.0429 (8)
H1A	0.7601	0.5058	0.2853	0.052*
N2	0.4584 (4)	0.3389 (3)	0.2740 (3)	0.0531 (10)
N3	0.3946 (4)	0.1531 (3)	0.2488 (3)	0.0524 (10)
N4	0.5138 (4)	0.2917 (3)	0.2161 (2)	0.0397 (8)
C1	1.0942 (6)	0.4214 (5)	0.3759 (4)	0.0718 (16)
H1B	1.0917	0.3544	0.3439	0.086*
C2	1.2294 (6)	0.4598 (6)	0.4417 (5)	0.0822 (18)
H2B	1.3147	0.4164	0.4549	0.099*
C3	1.2353 (7)	0.5587 (5)	0.4858 (4)	0.0774 (17)
H3B	1.3250	0.5843	0.5281	0.093*
C4	1.1087 (7)	0.6236 (5)	0.4688 (4)	0.0763 (17)
H4A	1.1142	0.6915	0.5003	0.092*
C5	0.9748 (6)	0.5876 (4)	0.4052 (4)	0.0634 (14)
H5A	0.8902	0.6317	0.3925	0.076*
C6	0.9679 (5)	0.4812 (4)	0.3589 (3)	0.0482 (11)
C7	0.7697 (5)	0.3541 (3)	0.2516 (3)	0.0393 (9)
C8	0.6075 (4)	0.3643 (3)	0.1851 (3)	0.0390 (9)
H8A	0.5765	0.4439	0.1860	0.047*
C9	0.3868 (6)	0.2520 (4)	0.2905 (4)	0.0580 (12)
H9A	0.3344	0.2584	0.3279	0.070*
C10	0.4757 (5)	0.1814 (4)	0.2029 (3)	0.0504 (11)
H10A	0.5022	0.1318	0.1662	0.060*
C11	0.5935 (4)	0.3365 (3)	0.0889 (3)	0.0383 (9)
C12	0.6662 (4)	0.4152 (3)	0.0455 (3)	0.0392 (9)
C13	0.7097 (5)	0.5280 (3)	0.0766 (3)	0.0430 (10)
H13A	0.6944	0.5552	0.1269	0.052*
C14	0.7741 (5)	0.5974 (4)	0.0335 (3)	0.0496 (11)
H14A	0.8021	0.6714	0.0545	0.060*
C15	0.7982 (5)	0.5574 (4)	−0.0423 (3)	0.0464 (10)
C16	0.7521 (5)	0.4478 (4)	−0.0749 (3)	0.0499 (11)
H16A	0.7650	0.4211	−0.1262	0.060*
C17	0.6870 (5)	0.3790 (4)	−0.0307 (3)	0.0451 (10)
H17A	0.6562	0.3059	−0.0530	0.054*
C18	0.9067 (6)	0.5924 (5)	−0.1494 (4)	0.0710 (16)
H18A	0.9528	0.6530	−0.1695	0.106*
H18B	0.8206	0.5664	−0.1990	0.106*
H18C	0.9750	0.5300	−0.1272	0.106*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
S1	0.0472 (7)	0.0431 (6)	0.0713 (9)	0.0051 (5)	0.0165 (6)	0.0064 (5)
O1	0.056 (2)	0.0549 (18)	0.0482 (18)	−0.0127 (14)	0.0182 (16)	−0.0077 (14)
O2	0.072 (2)	0.0598 (19)	0.061 (2)	−0.0083 (16)	0.0349 (19)	0.0062 (16)
N1	0.039 (2)	0.0492 (19)	0.040 (2)	0.0020 (15)	0.0137 (16)	−0.0059 (15)
N2	0.057 (2)	0.055 (2)	0.060 (3)	0.0002 (17)	0.036 (2)	0.0024 (17)
N3	0.048 (2)	0.053 (2)	0.062 (3)	−0.0102 (16)	0.027 (2)	0.0060 (17)
N4	0.0376 (19)	0.0394 (17)	0.048 (2)	−0.0030 (13)	0.0229 (16)	−0.0003 (14)
C1	0.059 (3)	0.077 (4)	0.073 (4)	0.000 (3)	0.018 (3)	−0.020 (3)
C2	0.045 (3)	0.094 (4)	0.096 (5)	0.000 (3)	0.015 (3)	−0.006 (4)
C3	0.056 (4)	0.088 (4)	0.083 (4)	−0.014 (3)	0.020 (3)	−0.005 (3)
C4	0.081 (4)	0.071 (3)	0.069 (4)	−0.019 (3)	0.021 (3)	−0.012 (3)
C5	0.058 (3)	0.059 (3)	0.068 (3)	−0.010 (2)	0.018 (3)	−0.003 (2)
C6	0.037 (2)	0.070 (3)	0.037 (2)	0.002 (2)	0.013 (2)	−0.005 (2)
C7	0.038 (2)	0.047 (2)	0.038 (2)	−0.0040 (16)	0.0203 (19)	0.0042 (16)
C8	0.039 (2)	0.0373 (19)	0.043 (2)	−0.0004 (16)	0.0184 (19)	0.0019 (16)
C9	0.060 (3)	0.059 (3)	0.067 (3)	0.003 (2)	0.038 (3)	0.011 (2)
C10	0.053 (3)	0.045 (2)	0.058 (3)	−0.008 (2)	0.027 (2)	−0.001 (2)
C11	0.036 (2)	0.040 (2)	0.037 (2)	0.0047 (16)	0.0109 (18)	0.0009 (16)
C12	0.033 (2)	0.044 (2)	0.037 (2)	0.0058 (16)	0.0096 (18)	0.0030 (16)
C13	0.050 (3)	0.040 (2)	0.043 (2)	0.0039 (17)	0.024 (2)	−0.0020 (17)
C14	0.059 (3)	0.043 (2)	0.050 (3)	0.0002 (19)	0.025 (2)	0.0019 (18)
C15	0.040 (2)	0.051 (2)	0.046 (3)	0.0049 (18)	0.014 (2)	0.0097 (19)
C16	0.058 (3)	0.055 (2)	0.038 (2)	0.001 (2)	0.020 (2)	−0.0022 (19)
C17	0.048 (3)	0.047 (2)	0.039 (2)	−0.0011 (18)	0.015 (2)	−0.0013 (18)
C18	0.061 (3)	0.091 (4)	0.075 (4)	0.011 (3)	0.041 (3)	0.028 (3)

Geometric parameters (Å, º)

S1—C7	1.653 (4)	C5—C6	1.434 (6)
O1—C11	1.217 (4)	C5—H5A	0.9300
O2—C15	1.379 (5)	C7—C8	1.542 (6)
O2—C18	1.389 (6)	C8—C11	1.527 (6)
N1—C7	1.339 (5)	C8—H8A	0.9801
N1—C6	1.427 (5)	C9—H9A	0.9300
N1—H1A	0.8601	C10—H10A	0.9300
N2—C9	1.317 (6)	C11—C12	1.487 (6)
N2—N4	1.359 (5)	C12—C17	1.378 (6)
N3—C10	1.314 (6)	C12—C13	1.415 (5)
N3—C9	1.352 (6)	C13—C14	1.365 (6)
N4—C10	1.334 (5)	C13—H13A	0.9299
N4—C8	1.469 (5)	C14—C15	1.401 (6)
C1—C6	1.355 (7)	C14—H14A	0.9300
C1—C2	1.414 (8)	C15—C16	1.391 (6)
C1—H1B	0.9300	C16—C17	1.379 (6)
C2—C3	1.343 (8)	C16—H16A	0.9301
C2—H2B	0.9301	C17—H17A	0.9299
C3—C4	1.389 (8)	C18—H18A	0.9600
C3—H3B	0.9300	C18—H18B	0.9600
C4—C5	1.383 (7)	C18—H18C	0.9602
C4—H4A	0.9299
C15—O2—C18	118.1 (4)	C7—C8—H8A	107.9
C7—N1—C6	131.6 (4)	N2—C9—N3	115.1 (4)
C7—N1—H1A	114.2	N2—C9—H9A	122.4
C6—N1—H1A	114.2	N3—C9—H9A	122.5
C9—N2—N4	101.9 (4)	N3—C10—N4	110.3 (4)
C10—N3—C9	102.8 (4)	N3—C10—H10A	124.8
C10—N4—N2	109.8 (3)	N4—C10—H10A	124.9
C10—N4—C8	132.6 (4)	O1—C11—C12	121.2 (4)
N2—N4—C8	117.4 (3)	O1—C11—C8	121.1 (4)
C6—C1—C2	120.6 (5)	C12—C11—C8	117.7 (3)
C6—C1—H1B	119.6	C17—C12—C13	118.0 (4)
C2—C1—H1B	119.7	C17—C12—C11	118.9 (4)
C3—C2—C1	120.2 (6)	C13—C12—C11	123.0 (4)
C3—C2—H2B	119.7	C14—C13—C12	120.7 (4)
C1—C2—H2B	120.1	C14—C13—H13A	119.6
C2—C3—C4	120.7 (6)	C12—C13—H13A	119.7
C2—C3—H3B	119.8	C13—C14—C15	120.3 (4)
C4—C3—H3B	119.5	C13—C14—H14A	119.9
C5—C4—C3	120.2 (6)	C15—C14—H14A	119.9
C5—C4—H4A	119.9	O2—C15—C16	124.2 (4)
C3—C4—H4A	119.8	O2—C15—C14	116.3 (4)
C4—C5—C6	119.1 (5)	C16—C15—C14	119.5 (4)
C4—C5—H5A	120.5	C17—C16—C15	119.4 (4)
C6—C5—H5A	120.4	C17—C16—H16A	120.2
C1—C6—N1	126.7 (4)	C15—C16—H16A	120.4
C1—C6—C5	119.0 (5)	C12—C17—C16	122.1 (4)
N1—C6—C5	114.3 (4)	C12—C17—H17A	119.0
N1—C7—C8	113.3 (3)	C16—C17—H17A	118.9
N1—C7—S1	128.2 (3)	O2—C18—H18A	109.4
C8—C7—S1	118.5 (3)	O2—C18—H18B	109.5
N4—C8—C11	113.0 (3)	H18A—C18—H18B	109.5
N4—C8—C7	109.7 (3)	O2—C18—H18C	109.5
C11—C8—C7	110.4 (3)	H18A—C18—H18C	109.5
N4—C8—H8A	107.8	H18B—C18—H18C	109.5
C11—C8—H8A	107.9

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1A···N3^i	0.86	2.22	3.076 (5)	175
C1—H1B···S1	0.93	2.62	3.256 (6)	126
C8—H8A···N3^i	0.98	2.63	3.537 (5)	154
C10—H10A···O1	0.93	2.42	2.811 (6)	105

Symmetry code: (i) −x+1, y+1/2, −z+1/2.