1-(2-Benzoyl-1-phenyl-eth-yl)-4-[(2-hy-droxy-1-naphth-yl)methyl-idene-amino]-3-phenyl-1H-1,2,4-triazole-5(4H)-thione.

In the title mol-ecule, C(34)H(26)N(4)O(2)S, the hy-droxy group is involved in an intra-molecular O-H⋯N hydrogen bond. The naphthyl ring system and the central triazole ring form a dihedral angle of 37.8 (1)°. The crystal packing exhibits weak inter-molecular C-H⋯O and C-H⋯π inter-actions.

Related literature

For the pharmacological properties and applications of Mannich bases, see: Joshi et al. (2004 ▶); Holla et al. (2003 ▶); Negm et al. (2005 ▶). For a related structure, see: Wang et al. (2011 ▶). For standard bond lengths, see: Allen et al. (1987 ▶).

Experimental

Crystal data

C34H26N4O2S

M = 554.65

Monoclinic,

a = 13.142 (3) Å

b = 21.563 (4) Å

c = 10.097 (2) Å

β = 99.22 (3)°

V = 2824.4 (10) Å3

Z = 4

Mo Kα radiation

μ = 0.15 mm−1

T = 113 K

0.20 × 0.18 × 0.10 mm

Data collection

Rigaku Saturn CCD area-detector diffractometer

Absorption correction: multi-scan (CrystalClear; Rigaku/MSC, 2005 ▶) T min = 0.970, T max = 0.985

23204 measured reflections

4960 independent reflections

4082 reflections with I > 2σ(I)

R int = 0.054

Refinement

R[F 2 > 2σ(F 2)] = 0.045

wR(F 2) = 0.142

S = 1.11

4960 reflections

372 parameters

H-atom parameters constrained

Δρmax = 0.34 e Å−3

Δρmin = −0.31 e Å−3

Data collection: CrystalClear (Rigaku/MSC, 2005 ▶); cell refinement: CrystalClear; data reduction: CrystalClear; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: SHELXTL (Sheldrick, 2008 ▶); software used to prepare material for publication: SHELXTL.

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536811005721/cv5051sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536811005721/cv5051Isup2.hkl

Additional supplementary materials: crystallographic information; 3D view; checkCIF report

C34H26N4O2S	F(000) = 1160
Mr = 554.65	Dx = 1.304 Mg m−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 7260 reflections
a = 13.142 (3) Å	θ = 1.6–28.0°
b = 21.563 (4) Å	µ = 0.15 mm−1
c = 10.097 (2) Å	T = 113 K
β = 99.22 (3)°	Prism, colorless
V = 2824.4 (10) Å3	0.20 × 0.18 × 0.10 mm
Z = 4

Rigaku Saturn CCD area-detector diffractometer	4960 independent reflections
Radiation source: rotating anode	4082 reflections with I > 2σ(I)
confocal	Rint = 0.054
Detector resolution: 7.31 pixels mm-1	θmax = 25.0°, θmin = 1.6°
φ and ω scans	h = −15→15
Absorption correction: multi-scan (CrystalClear; Rigaku/MSC, 2005)	k = −25→25
Tmin = 0.970, Tmax = 0.985	l = −12→11
23204 measured reflections

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)] = 0.045	H-atom parameters constrained
wR(F2) = 0.142	w = 1/[σ2(Fo2) + (0.0813P)2 + 0.4421P] where P = (Fo2 + 2Fc2)/3
S = 1.11	(Δ/σ)max = 0.001
4960 reflections	Δρmax = 0.34 e Å−3
372 parameters	Δρmin = −0.31 e Å−3
0 restraints	Extinction correction: SHELXL97 (Sheldrick, 2008), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.0240 (19)

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
S1	0.16625 (4)	0.42969 (3)	0.53137 (5)	0.02488 (19)
O1	0.08098 (12)	0.59528 (7)	0.32929 (16)	0.0304 (4)
O2	0.56113 (11)	0.45741 (7)	0.40769 (15)	0.0256 (4)
H2	0.4993	0.4598	0.3708	0.038*
N1	0.10577 (13)	0.46429 (8)	0.27235 (17)	0.0199 (4)
N2	0.14223 (13)	0.47373 (8)	0.15336 (17)	0.0218 (4)
N3	0.26474 (13)	0.43820 (8)	0.30946 (16)	0.0185 (4)
N4	0.36713 (13)	0.43073 (8)	0.37079 (17)	0.0195 (4)
C1	−0.00280 (15)	0.47524 (10)	0.2847 (2)	0.0201 (5)
H1	−0.0055	0.4847	0.3810	0.024*
C2	−0.06940 (16)	0.41850 (9)	0.2465 (2)	0.0217 (5)
C3	−0.06416 (17)	0.38507 (11)	0.1301 (2)	0.0285 (5)
H3	−0.0143	0.3957	0.0754	0.034*
C4	−0.13163 (19)	0.33608 (11)	0.0934 (2)	0.0339 (6)
H4	−0.1275	0.3132	0.0140	0.041*
C5	−0.20463 (18)	0.32055 (11)	0.1720 (2)	0.0336 (6)
H5	−0.2514	0.2875	0.1458	0.040*
C6	−0.20963 (19)	0.35305 (11)	0.2889 (3)	0.0351 (6)
H6	−0.2596	0.3423	0.3433	0.042*
C7	−0.14105 (17)	0.40157 (10)	0.3265 (2)	0.0279 (5)
H7	−0.1435	0.4233	0.4078	0.034*
C8	−0.04660 (15)	0.53104 (9)	0.2024 (2)	0.0200 (5)
H8A	−0.0383	0.5241	0.1078	0.024*
H8B	−0.1214	0.5336	0.2053	0.024*
C9	0.00226 (16)	0.59267 (10)	0.2479 (2)	0.0220 (5)
C10	−0.04771 (17)	0.65007 (10)	0.1847 (2)	0.0258 (5)
C11	−0.14383 (19)	0.64937 (11)	0.1051 (3)	0.0436 (7)
H11	−0.1822	0.6119	0.0939	0.052*
C12	−0.1845 (2)	0.70293 (13)	0.0417 (4)	0.0623 (10)
H12	−0.2502	0.7019	−0.0133	0.075*
C13	−0.1304 (2)	0.75742 (12)	0.0580 (4)	0.0585 (9)
H13	−0.1582	0.7939	0.0135	0.070*
C14	−0.0359 (2)	0.75920 (12)	0.1386 (3)	0.0514 (8)
H14	0.0014	0.7970	0.1507	0.062*
C15	0.00491 (19)	0.70596 (11)	0.2024 (3)	0.0388 (6)
H15	0.0699	0.7077	0.2592	0.047*
C16	0.17801 (16)	0.44309 (9)	0.3722 (2)	0.0191 (5)
C17	0.24002 (15)	0.45884 (9)	0.1792 (2)	0.0193 (5)
C18	0.31025 (15)	0.45953 (9)	0.0795 (2)	0.0194 (5)
C19	0.29602 (16)	0.50478 (10)	−0.0206 (2)	0.0222 (5)
H19	0.2473	0.5371	−0.0175	0.027*
C20	0.35328 (17)	0.50241 (11)	−0.1249 (2)	0.0269 (5)
H20	0.3431	0.5329	−0.1936	0.032*
C21	0.42476 (17)	0.45594 (10)	−0.1289 (2)	0.0282 (5)
H21	0.4633	0.4543	−0.2008	0.034*
C22	0.44066 (18)	0.41152 (10)	−0.0284 (2)	0.0273 (5)
H22	0.4906	0.3799	−0.0313	0.033*
C23	0.38430 (17)	0.41304 (10)	0.0757 (2)	0.0234 (5)
H23	0.3957	0.3827	0.1446	0.028*
C24	0.38344 (16)	0.39135 (9)	0.4677 (2)	0.0203 (5)
H24	0.3278	0.3674	0.4899	0.024*
C25	0.48594 (15)	0.38324 (9)	0.5431 (2)	0.0176 (4)
C26	0.50280 (16)	0.33939 (9)	0.6524 (2)	0.0207 (5)
C27	0.42351 (17)	0.30223 (10)	0.6923 (2)	0.0269 (5)
H27	0.3546	0.3065	0.6473	0.032*
C28	0.4453 (2)	0.26033 (11)	0.7947 (2)	0.0343 (6)
H28	0.3911	0.2359	0.8196	0.041*
C29	0.5456 (2)	0.25274 (11)	0.8635 (3)	0.0362 (6)
H29	0.5598	0.2230	0.9336	0.043*
C30	0.62286 (19)	0.28835 (11)	0.8292 (2)	0.0302 (5)
H30	0.6908	0.2838	0.8772	0.036*
C31	0.60419 (16)	0.33192 (9)	0.7236 (2)	0.0219 (5)
C32	0.68548 (17)	0.36873 (11)	0.6870 (2)	0.0263 (5)
H32	0.7530	0.3644	0.7363	0.032*
C33	0.66934 (17)	0.40962 (10)	0.5842 (2)	0.0240 (5)
H33	0.7251	0.4333	0.5615	0.029*
C34	0.56926 (16)	0.41697 (9)	0.5107 (2)	0.0198 (5)

	U11	U22	U33	U12	U13	U23
S1	0.0264 (3)	0.0314 (3)	0.0177 (3)	0.0045 (2)	0.0061 (2)	0.0032 (2)
O1	0.0231 (9)	0.0351 (9)	0.0309 (9)	−0.0044 (7)	−0.0023 (7)	0.0010 (7)
O2	0.0212 (8)	0.0302 (8)	0.0252 (8)	−0.0010 (7)	0.0030 (7)	0.0093 (6)
N1	0.0171 (9)	0.0269 (9)	0.0164 (9)	0.0009 (7)	0.0042 (7)	0.0027 (7)
N2	0.0191 (10)	0.0273 (10)	0.0191 (9)	−0.0007 (7)	0.0034 (7)	0.0012 (7)
N3	0.0155 (9)	0.0240 (9)	0.0161 (9)	0.0012 (7)	0.0025 (7)	0.0015 (7)
N4	0.0157 (10)	0.0243 (9)	0.0179 (9)	0.0026 (7)	0.0006 (7)	−0.0005 (7)
C1	0.0145 (11)	0.0259 (11)	0.0203 (11)	0.0023 (9)	0.0041 (9)	0.0010 (8)
C2	0.0189 (11)	0.0220 (11)	0.0228 (11)	0.0028 (9)	−0.0006 (9)	0.0065 (8)
C3	0.0274 (13)	0.0348 (13)	0.0236 (12)	−0.0045 (10)	0.0050 (10)	0.0019 (10)
C4	0.0367 (15)	0.0356 (13)	0.0284 (13)	−0.0017 (11)	0.0022 (11)	−0.0063 (10)
C5	0.0302 (13)	0.0289 (12)	0.0394 (14)	−0.0082 (10)	−0.0012 (11)	−0.0017 (11)
C6	0.0322 (14)	0.0309 (13)	0.0449 (15)	−0.0064 (10)	0.0143 (12)	−0.0007 (11)
C7	0.0291 (13)	0.0257 (12)	0.0308 (13)	−0.0022 (10)	0.0099 (10)	−0.0018 (9)
C8	0.0153 (11)	0.0251 (11)	0.0203 (11)	0.0016 (9)	0.0047 (9)	0.0014 (8)
C9	0.0175 (12)	0.0288 (12)	0.0205 (11)	−0.0014 (9)	0.0052 (10)	−0.0013 (9)
C10	0.0228 (12)	0.0243 (11)	0.0295 (12)	−0.0005 (9)	0.0019 (10)	−0.0032 (9)
C11	0.0357 (15)	0.0201 (12)	0.0666 (19)	−0.0040 (11)	−0.0176 (13)	0.0025 (12)
C12	0.0496 (18)	0.0281 (14)	0.094 (3)	0.0010 (13)	−0.0344 (17)	0.0071 (15)
C13	0.056 (2)	0.0201 (13)	0.089 (2)	0.0032 (12)	−0.0187 (17)	0.0064 (14)
C14	0.0482 (18)	0.0201 (13)	0.080 (2)	−0.0075 (12)	−0.0076 (16)	−0.0020 (13)
C15	0.0307 (14)	0.0249 (12)	0.0572 (17)	−0.0034 (10)	−0.0032 (12)	−0.0045 (11)
C16	0.0194 (11)	0.0160 (10)	0.0222 (11)	−0.0004 (8)	0.0045 (9)	0.0004 (8)
C17	0.0170 (11)	0.0203 (10)	0.0202 (11)	−0.0019 (8)	0.0018 (9)	0.0014 (8)
C18	0.0152 (11)	0.0236 (11)	0.0190 (11)	−0.0027 (8)	0.0013 (9)	−0.0013 (8)
C19	0.0185 (11)	0.0252 (11)	0.0219 (11)	0.0002 (9)	0.0006 (9)	0.0010 (9)
C20	0.0273 (12)	0.0318 (12)	0.0212 (12)	−0.0027 (10)	0.0026 (10)	0.0023 (9)
C21	0.0289 (13)	0.0355 (13)	0.0217 (12)	−0.0049 (10)	0.0087 (10)	−0.0037 (10)
C22	0.0257 (12)	0.0309 (12)	0.0264 (12)	0.0018 (10)	0.0072 (10)	−0.0049 (9)
C23	0.0228 (12)	0.0244 (11)	0.0219 (12)	0.0010 (9)	0.0002 (9)	0.0007 (9)
C24	0.0206 (12)	0.0198 (10)	0.0209 (11)	0.0002 (8)	0.0047 (9)	−0.0021 (8)
C25	0.0183 (11)	0.0181 (10)	0.0168 (10)	0.0027 (8)	0.0040 (8)	−0.0023 (8)
C26	0.0240 (12)	0.0199 (11)	0.0186 (11)	0.0009 (9)	0.0048 (9)	−0.0002 (8)
C27	0.0260 (13)	0.0278 (12)	0.0268 (12)	−0.0034 (9)	0.0035 (10)	0.0048 (9)
C28	0.0408 (15)	0.0279 (12)	0.0360 (14)	−0.0050 (11)	0.0113 (12)	0.0096 (10)
C29	0.0446 (16)	0.0325 (13)	0.0318 (14)	0.0051 (11)	0.0068 (12)	0.0150 (10)
C30	0.0313 (13)	0.0322 (13)	0.0264 (12)	0.0093 (10)	0.0020 (10)	0.0062 (10)
C31	0.0225 (12)	0.0228 (11)	0.0204 (11)	0.0056 (9)	0.0032 (9)	−0.0012 (8)
C32	0.0200 (12)	0.0322 (12)	0.0252 (12)	0.0034 (9)	−0.0010 (9)	−0.0008 (9)
C33	0.0189 (12)	0.0287 (12)	0.0250 (12)	0.0003 (9)	0.0057 (9)	−0.0007 (9)
C34	0.0235 (12)	0.0210 (10)	0.0153 (10)	−0.0003 (9)	0.0036 (9)	−0.0015 (8)

S1—C16	1.665 (2)	C13—C14	1.372 (4)
O1—C9	1.215 (3)	C13—H13	0.9500
O2—C34	1.349 (2)	C14—C15	1.382 (4)
O2—H2	0.8400	C14—H14	0.9500
N1—C16	1.349 (3)	C15—H15	0.9500
N1—N2	1.378 (2)	C17—C18	1.471 (3)
N1—C1	1.471 (3)	C18—C19	1.396 (3)
N2—C17	1.310 (3)	C18—C23	1.402 (3)
N3—C17	1.377 (3)	C19—C20	1.390 (3)
N3—C16	1.394 (3)	C19—H19	0.9500
N3—N4	1.397 (2)	C20—C21	1.379 (3)
N4—C24	1.287 (3)	C20—H20	0.9500
C1—C2	1.518 (3)	C21—C22	1.387 (3)
C1—C8	1.522 (3)	C21—H21	0.9500
C1—H1	1.0000	C22—C23	1.380 (3)
C2—C7	1.384 (3)	C22—H22	0.9500
C2—C3	1.390 (3)	C23—H23	0.9500
C3—C4	1.391 (3)	C24—C25	1.448 (3)
C3—H3	0.9500	C24—H24	0.9500
C4—C5	1.381 (3)	C25—C34	1.396 (3)
C4—H4	0.9500	C25—C26	1.444 (3)
C5—C6	1.383 (3)	C26—C31	1.418 (3)
C5—H5	0.9500	C26—C27	1.423 (3)
C6—C7	1.393 (3)	C27—C28	1.369 (3)
C6—H6	0.9500	C27—H27	0.9500
C7—H7	0.9500	C28—C29	1.398 (4)
C8—C9	1.515 (3)	C28—H28	0.9500
C8—H8A	0.9900	C29—C30	1.361 (3)
C8—H8B	0.9900	C29—H29	0.9500
C9—C10	1.495 (3)	C30—C31	1.412 (3)
C10—C11	1.384 (3)	C30—H30	0.9500
C10—C15	1.387 (3)	C31—C32	1.426 (3)
C11—C12	1.385 (3)	C32—C33	1.353 (3)
C11—H11	0.9500	C32—H32	0.9500
C12—C13	1.370 (4)	C33—C34	1.411 (3)
C12—H12	0.9500	C33—H33	0.9500
C34—O2—H2	109.5	C10—C15—H15	119.6
C16—N1—N2	113.59 (16)	N1—C16—N3	102.42 (16)
C16—N1—C1	124.56 (17)	N1—C16—S1	128.11 (16)
N2—N1—C1	121.84 (17)	N3—C16—S1	129.41 (16)
C17—N2—N1	104.91 (17)	N2—C17—N3	110.08 (18)
C17—N3—C16	108.93 (16)	N2—C17—C18	124.36 (19)
C17—N3—N4	121.57 (16)	N3—C17—C18	125.38 (18)
C16—N3—N4	127.36 (16)	C19—C18—C23	119.5 (2)
C24—N4—N3	116.37 (17)	C19—C18—C17	118.47 (18)
N1—C1—C2	112.14 (16)	C23—C18—C17	121.73 (19)
N1—C1—C8	111.58 (16)	C20—C19—C18	119.8 (2)
C2—C1—C8	110.26 (17)	C20—C19—H19	120.1
N1—C1—H1	107.5	C18—C19—H19	120.1
C2—C1—H1	107.5	C21—C20—C19	120.2 (2)
C8—C1—H1	107.5	C21—C20—H20	119.9
C7—C2—C3	119.2 (2)	C19—C20—H20	119.9
C7—C2—C1	118.89 (19)	C20—C21—C22	120.3 (2)
C3—C2—C1	121.87 (19)	C20—C21—H21	119.9
C2—C3—C4	120.2 (2)	C22—C21—H21	119.9
C2—C3—H3	119.9	C23—C22—C21	120.3 (2)
C4—C3—H3	119.9	C23—C22—H22	119.8
C5—C4—C3	120.2 (2)	C21—C22—H22	119.8
C5—C4—H4	119.9	C22—C23—C18	119.8 (2)
C3—C4—H4	119.9	C22—C23—H23	120.1
C4—C5—C6	120.0 (2)	C18—C23—H23	120.1
C4—C5—H5	120.0	N4—C24—C25	120.45 (19)
C6—C5—H5	120.0	N4—C24—H24	119.8
C5—C6—C7	119.7 (2)	C25—C24—H24	119.8
C5—C6—H6	120.1	C34—C25—C26	119.34 (19)
C7—C6—H6	120.1	C34—C25—C24	120.85 (18)
C2—C7—C6	120.7 (2)	C26—C25—C24	119.80 (18)
C2—C7—H7	119.7	C31—C26—C27	117.64 (19)
C6—C7—H7	119.7	C31—C26—C25	118.60 (19)
C9—C8—C1	115.01 (18)	C27—C26—C25	123.76 (19)
C9—C8—H8A	108.5	C28—C27—C26	120.8 (2)
C1—C8—H8A	108.5	C28—C27—H27	119.6
C9—C8—H8B	108.5	C26—C27—H27	119.6
C1—C8—H8B	108.5	C27—C28—C29	121.3 (2)
H8A—C8—H8B	107.5	C27—C28—H28	119.4
O1—C9—C10	121.2 (2)	C29—C28—H28	119.4
O1—C9—C8	121.3 (2)	C30—C29—C28	119.3 (2)
C10—C9—C8	117.44 (19)	C30—C29—H29	120.3
C11—C10—C15	118.3 (2)	C28—C29—H29	120.3
C11—C10—C9	122.4 (2)	C29—C30—C31	121.4 (2)
C15—C10—C9	119.2 (2)	C29—C30—H30	119.3
C10—C11—C12	120.5 (2)	C31—C30—H30	119.3
C10—C11—H11	119.8	C30—C31—C26	119.6 (2)
C12—C11—H11	119.8	C30—C31—C32	121.3 (2)
C13—C12—C11	120.4 (3)	C26—C31—C32	119.16 (19)
C13—C12—H12	119.8	C33—C32—C31	122.0 (2)
C11—C12—H12	119.8	C33—C32—H32	119.0
C12—C13—C14	119.9 (3)	C31—C32—H32	119.0
C12—C13—H13	120.1	C32—C33—C34	119.7 (2)
C14—C13—H13	120.1	C32—C33—H33	120.2
C13—C14—C15	120.0 (2)	C34—C33—H33	120.2
C13—C14—H14	120.0	O2—C34—C25	123.30 (19)
C15—C14—H14	120.0	O2—C34—C33	115.47 (18)
C14—C15—C10	120.9 (2)	C25—C34—C33	121.22 (19)
C14—C15—H15	119.6
C16—N1—N2—C17	−0.8 (2)	N1—N2—C17—C18	177.69 (18)
C1—N1—N2—C17	−179.26 (17)	C16—N3—C17—N2	−3.0 (2)
C17—N3—N4—C24	−154.97 (19)	N4—N3—C17—N2	−167.49 (16)
C16—N3—N4—C24	43.5 (3)	C16—N3—C17—C18	−178.37 (19)
C16—N1—C1—C2	−90.8 (2)	N4—N3—C17—C18	17.1 (3)
N2—N1—C1—C2	87.5 (2)	N2—C17—C18—C19	34.5 (3)
C16—N1—C1—C8	144.92 (19)	N3—C17—C18—C19	−150.7 (2)
N2—N1—C1—C8	−36.7 (3)	N2—C17—C18—C23	−139.8 (2)
N1—C1—C2—C7	136.1 (2)	N3—C17—C18—C23	35.0 (3)
C8—C1—C2—C7	−98.9 (2)	C23—C18—C19—C20	1.7 (3)
N1—C1—C2—C3	−47.3 (3)	C17—C18—C19—C20	−172.70 (19)
C8—C1—C2—C3	77.7 (2)	C18—C19—C20—C21	−0.7 (3)
C7—C2—C3—C4	1.3 (3)	C19—C20—C21—C22	−0.5 (3)
C1—C2—C3—C4	−175.3 (2)	C20—C21—C22—C23	0.7 (3)
C2—C3—C4—C5	0.4 (4)	C21—C22—C23—C18	0.3 (3)
C3—C4—C5—C6	−1.1 (4)	C19—C18—C23—C22	−1.5 (3)
C4—C5—C6—C7	0.3 (4)	C17—C18—C23—C22	172.7 (2)
C3—C2—C7—C6	−2.2 (3)	N3—N4—C24—C25	−176.06 (16)
C1—C2—C7—C6	174.5 (2)	N4—C24—C25—C34	−1.2 (3)
C5—C6—C7—C2	1.4 (4)	N4—C24—C25—C26	179.30 (18)
N1—C1—C8—C9	−64.8 (2)	C34—C25—C26—C31	−0.2 (3)
C2—C1—C8—C9	169.89 (17)	C24—C25—C26—C31	179.34 (18)
C1—C8—C9—O1	11.4 (3)	C34—C25—C26—C27	−179.18 (19)
C1—C8—C9—C10	−170.98 (18)	C24—C25—C26—C27	0.3 (3)
O1—C9—C10—C11	−171.5 (2)	C31—C26—C27—C28	−0.8 (3)
C8—C9—C10—C11	10.9 (3)	C25—C26—C27—C28	178.3 (2)
O1—C9—C10—C15	10.5 (3)	C26—C27—C28—C29	0.1 (4)
C8—C9—C10—C15	−167.1 (2)	C27—C28—C29—C30	0.9 (4)
C15—C10—C11—C12	2.0 (4)	C28—C29—C30—C31	−1.3 (4)
C9—C10—C11—C12	−175.9 (3)	C29—C30—C31—C26	0.6 (3)
C10—C11—C12—C13	−0.6 (5)	C29—C30—C31—C32	−179.4 (2)
C11—C12—C13—C14	−0.7 (6)	C27—C26—C31—C30	0.4 (3)
C12—C13—C14—C15	0.6 (5)	C25—C26—C31—C30	−178.68 (19)
C13—C14—C15—C10	0.9 (5)	C27—C26—C31—C32	−179.57 (19)
C11—C10—C15—C14	−2.2 (4)	C25—C26—C31—C32	1.4 (3)
C9—C10—C15—C14	175.8 (2)	C30—C31—C32—C33	178.4 (2)
N2—N1—C16—N3	−1.0 (2)	C26—C31—C32—C33	−1.6 (3)
C1—N1—C16—N3	177.48 (17)	C31—C32—C33—C34	0.6 (3)
N2—N1—C16—S1	176.44 (15)	C26—C25—C34—O2	177.88 (18)
C1—N1—C16—S1	−5.1 (3)	C24—C25—C34—O2	−1.6 (3)
C17—N3—C16—N1	2.3 (2)	C26—C25—C34—C33	−0.9 (3)
N4—N3—C16—N1	165.67 (17)	C24—C25—C34—C33	179.63 (18)
C17—N3—C16—S1	−175.07 (16)	C32—C33—C34—O2	−178.16 (19)
N4—N3—C16—S1	−11.7 (3)	C32—C33—C34—C25	0.7 (3)
N1—N2—C17—N3	2.2 (2)

Cg1 is the centroid of the C2–C7 ring.

D—H···A	D—H	H···A	D···A	D—H···A
O2—H2···N4	0.84	1.85	2.582 (2)	145
C32—H32···O1i	0.95	2.53	3.196 (2)	127
C14—H14···Cg1ii	0.95	2.60	3.465 (2)	151

Table 1

Hydrogen-bond geometry (Å, °)

Cg1 is the centroid of the C2–C7 ring.

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O2—H2⋯N4	0.84	1.85	2.582 (2)	145
C32—H32⋯O1i	0.95	2.53	3.196 (2)	127
C14—H14⋯Cg1ii	0.95	2.60	3.465 (2)	151

Symmetry codes: (i) ; (ii) .