5-[3-(Quinolin-8-yl­oxy)prop­yl]-1,3,4-oxadiazole-2(3H)-thione

The title compound, C₁₄H₁₃N₃O₂S, crystallizes as a thione tautomer. There are two mol­ecules in the asymmetric unit which differ in conformation. The mol­ecules are connected via inter­molecular N—H...N and N—H...O hydrogen bonds into a one-dimensional helical structure.

Key indicators

• Single-crystal X-ray study
• T = 293 K
• Mean [sigma](C-C) = 0.003 Å
• R factor = 0.041
• wR factor = 0.138
• Data-to-parameter ratio = 13.0

checkCIF/PLATON results

No syntax errors found



Alert level C
PLAT066_ALERT_1_C Predicted and Reported Transmissions Identical .          ?
PLAT230_ALERT_2_C Hirshfeld Test Diff for    S1     -   C14     ..       5.54 su
PLAT230_ALERT_2_C Hirshfeld Test Diff for    S2     -   C28     ..       6.81 su

Alert level G
PLAT199_ALERT_1_G Check the Reported _cell_measurement_temperature        293 K
PLAT200_ALERT_1_G Check the Reported _diffrn_ambient_temperature .        293 K

   0 ALERT level A = In general: serious problem
   0 ALERT level B = Potentially serious problem
   3 ALERT level C = Check and explain
   2 ALERT level G = General alerts; check

   3 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
   2 ALERT type 2 Indicator that the structure model may be wrong or deficient
   0 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

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Computing details

Data collection: SMART (Siemens, 1996); cell refinement: SAINT (Siemens, 1996); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997a); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997a); molecular graphics: SHELXTL (Sheldrick, 1997b); software used to prepare material for publication: SHELXTL.

5-[3-(quinolin-8-yloxy)propyl]-1,3,4-oxadiazole-2(3H)-thione

Crystal data

C14H13N3O2S	Z = 4
Mr = 287.33	F(000) = 600
Triclinic, P1	Dx = 1.396 Mg m^−3
Hall symbol: -P 1	Melting point = 505–506 K
a = 7.3208 (5) Å	Mo Kα radiation, λ = 0.71073 Å
b = 11.5523 (7) Å	Cell parameters from 4804 reflections
c = 16.7934 (10) Å	θ = 2.9–28.3°
α = 84.271 (3)°	µ = 0.24 mm^−1
β = 89.326 (4)°	T = 293 K
γ = 75.357 (2)°	Block, colourless
V = 1367.13 (15) Å^3	0.44 × 0.26 × 0.15 mm

Data collection

Bruker SMART diffractometer	4781 independent reflections
Radiation source: fine-focus sealed tube	4241 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.015
Detector resolution: 0 pixels mm^-1	θmax = 25.0°, θmin = 2.1°
φ and ω scans	h = −8→7
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	k = −13→13
Tmin = 0.901, Tmax = 0.965	l = −19→16
7016 measured reflections

Refinement

Refinement on F^2	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F^2 > 2σ(F^2)] = 0.041	Hydrogen site location: difference Fourier map
wR(F^2) = 0.138	H atoms treated by a mixture of independent and constrained refinement
S = 1.00	w = 1/[σ^2(Fo^2) + (0.1P)^2 + 0.33P] where P = (Fo^2 + 2Fc^2)/3
4781 reflections	(Δ/σ)max = 0.001
369 parameters	Δρmax = 0.46 e Å^−3
1 restraint	Δρmin = −0.32 e Å^−3

Special details

Experimental. Spectroscopic analysis: IR (KBr, ν cm-1): 3416, 2914, 1624, 1495; 1H NMR (DMSO, δ, p.p.m.): 14.29(s, 1H), 8.88 (d, 1H, J = 4 Hz), 8.30 (d, 1H, J = 8 Hz), 7.54 (d, 1H, J = 8 Hz), 7.51 (d, 1H, J = 7 Hz), 7.19 (d, 1H, J = 5 Hz), 4.26 (t, 2H), 3.00 (t, 2H), 2.25 (m, 2H)

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	0.55459 (8)	0.14652 (5)	0.27334 (3)	0.05210 (18)
S2	−0.33404 (7)	0.83235 (5)	0.21883 (3)	0.05425 (18)
O1	0.84410 (19)	0.67506 (12)	0.01799 (7)	0.0458 (3)
N1	1.1190 (2)	0.77074 (13)	0.06276 (8)	0.0371 (3)
O2	0.5681 (2)	0.35000 (11)	0.18582 (7)	0.0459 (3)
C9	1.0421 (2)	0.80514 (14)	−0.01226 (10)	0.0330 (4)
C1	0.8913 (3)	0.75818 (15)	−0.03658 (10)	0.0375 (4)
N3	0.7331 (2)	0.31973 (15)	0.29372 (10)	0.0467 (4)
C5	1.1090 (3)	0.88573 (16)	−0.06753 (11)	0.0398 (4)
C2	0.8089 (3)	0.79501 (18)	−0.11063 (11)	0.0478 (5)
H2	0.7090	0.7656	−0.1260	0.057*
C14	0.6235 (2)	0.27125 (16)	0.25322 (10)	0.0391 (4)
C8	1.2593 (3)	0.81476 (17)	0.08259 (12)	0.0451 (4)
H8	1.3093	0.7935	0.1342	0.054*
C3	0.8751 (3)	0.8773 (2)	−0.16368 (11)	0.0535 (5)
H3	0.8173	0.9018	−0.2137	0.064*
C13	0.6477 (3)	0.44360 (17)	0.19297 (12)	0.0458 (4)
C4	1.0208 (3)	0.92131 (19)	−0.14351 (11)	0.0500 (5)
H4	1.0630	0.9750	−0.1797	0.060*
N2	0.7507 (3)	0.42893 (16)	0.25624 (10)	0.0545 (4)
C10	0.7262 (3)	0.60521 (19)	−0.01062 (12)	0.0490 (5)
H10A	0.7738	0.5746	−0.0606	0.059*
H10B	0.5981	0.6543	−0.0197	0.059*
C12	0.6187 (3)	0.54200 (17)	0.12697 (12)	0.0490 (5)
H12A	0.6575	0.6095	0.1449	0.059*
H12B	0.4855	0.5688	0.1130	0.059*
C7	1.3381 (3)	0.8913 (2)	0.03132 (13)	0.0556 (5)
H7	1.4408	0.9170	0.0479	0.067*
C11	0.7300 (3)	0.50193 (17)	0.05346 (12)	0.0484 (5)
H11A	0.6785	0.4425	0.0311	0.058*
H11B	0.8600	0.4639	0.0693	0.058*
C6	1.2619 (3)	0.92742 (19)	−0.04320 (13)	0.0533 (5)
H6	1.3108	0.9795	−0.0780	0.064*
O4	−0.12193 (17)	0.66246 (11)	0.32209 (7)	0.0420 (3)
N4	0.9454 (2)	0.21820 (14)	0.43023 (9)	0.0417 (4)
C23	0.8867 (3)	0.19785 (15)	0.50633 (10)	0.0364 (4)
O3	0.5918 (2)	0.32132 (13)	0.46437 (8)	0.0539 (4)
N6	0.0014 (2)	0.66991 (15)	0.20540 (10)	0.0452 (4)
C28	−0.1483 (3)	0.72059 (16)	0.24633 (11)	0.0405 (4)
C15	0.6960 (3)	0.25025 (16)	0.52624 (10)	0.0406 (4)
C19	1.0095 (3)	0.12336 (16)	0.56618 (11)	0.0406 (4)
N5	0.1302 (2)	0.58192 (15)	0.25324 (10)	0.0479 (4)
C26	0.1172 (3)	0.50825 (18)	0.39798 (11)	0.0462 (4)
H26A	0.0404	0.4519	0.4107	0.055*
H26B	0.1028	0.5606	0.4406	0.055*
C27	0.0480 (3)	0.58187 (16)	0.32131 (11)	0.0413 (4)
C24	0.3973 (3)	0.37590 (18)	0.47573 (12)	0.0464 (4)
H24A	0.3824	0.4332	0.5153	0.056*
H24B	0.3304	0.3156	0.4935	0.056*
C22	1.1205 (3)	0.16772 (19)	0.41242 (12)	0.0489 (5)
H22	1.1596	0.1819	0.3603	0.059*
C18	0.9403 (3)	0.10391 (19)	0.64383 (12)	0.0508 (5)
H18	1.0203	0.0564	0.6837	0.061*
C20	1.1966 (3)	0.07211 (19)	0.54403 (13)	0.0519 (5)
H20	1.2819	0.0237	0.5817	0.062*
C16	0.6326 (3)	0.22828 (19)	0.60181 (12)	0.0496 (5)
H16	0.5078	0.2619	0.6146	0.060*
C25	0.3228 (3)	0.43909 (19)	0.39430 (12)	0.0489 (5)
H25A	0.3982	0.4942	0.3757	0.059*
H25B	0.3351	0.3799	0.3562	0.059*
C17	0.7585 (3)	0.1540 (2)	0.66040 (12)	0.0555 (5)
H17	0.7146	0.1394	0.7117	0.067*
C21	1.2525 (3)	0.0934 (2)	0.46777 (13)	0.0546 (5)
H21	1.3754	0.0595	0.4525	0.066*
H1	0.797 (3)	0.287 (2)	0.3415 (15)	0.061 (7)*
H29	0.028 (3)	0.6960 (19)	0.1545 (14)	0.053 (6)*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
S1	0.0598 (3)	0.0471 (3)	0.0511 (3)	−0.0224 (2)	−0.0078 (2)	0.0113 (2)
S2	0.0482 (3)	0.0499 (3)	0.0574 (3)	−0.0031 (2)	−0.0050 (2)	0.0057 (2)
O1	0.0560 (8)	0.0532 (8)	0.0351 (7)	−0.0315 (6)	−0.0084 (6)	0.0098 (6)
N1	0.0405 (8)	0.0374 (8)	0.0326 (8)	−0.0104 (6)	−0.0039 (6)	0.0024 (6)
O2	0.0589 (8)	0.0431 (7)	0.0374 (7)	−0.0201 (6)	−0.0144 (6)	0.0089 (5)
C9	0.0364 (8)	0.0320 (8)	0.0290 (8)	−0.0072 (7)	0.0007 (6)	0.0002 (6)
C1	0.0447 (10)	0.0375 (9)	0.0314 (9)	−0.0147 (7)	−0.0020 (7)	0.0040 (7)
N3	0.0565 (10)	0.0517 (9)	0.0339 (8)	−0.0216 (8)	−0.0113 (7)	0.0081 (7)
C5	0.0437 (10)	0.0387 (9)	0.0372 (9)	−0.0136 (8)	0.0024 (7)	0.0027 (7)
C2	0.0549 (11)	0.0547 (11)	0.0375 (10)	−0.0239 (9)	−0.0112 (8)	0.0059 (8)
C14	0.0405 (9)	0.0421 (9)	0.0324 (9)	−0.0086 (7)	−0.0036 (7)	0.0040 (7)
C8	0.0447 (10)	0.0473 (10)	0.0425 (10)	−0.0113 (8)	−0.0108 (8)	−0.0001 (8)
C3	0.0697 (14)	0.0617 (12)	0.0307 (9)	−0.0254 (11)	−0.0115 (9)	0.0118 (8)
C13	0.0551 (11)	0.0436 (10)	0.0413 (10)	−0.0188 (9)	−0.0034 (9)	0.0002 (8)
C4	0.0645 (13)	0.0534 (11)	0.0340 (10)	−0.0247 (10)	0.0008 (9)	0.0111 (8)
N2	0.0705 (12)	0.0561 (10)	0.0435 (9)	−0.0319 (9)	−0.0116 (8)	0.0061 (8)
C10	0.0544 (11)	0.0561 (11)	0.0435 (10)	−0.0300 (10)	−0.0065 (9)	0.0042 (9)
C12	0.0557 (11)	0.0409 (10)	0.0496 (11)	−0.0130 (9)	−0.0061 (9)	0.0015 (8)
C7	0.0508 (12)	0.0632 (13)	0.0597 (13)	−0.0302 (10)	−0.0094 (10)	0.0031 (10)
C11	0.0510 (11)	0.0435 (10)	0.0543 (12)	−0.0205 (9)	0.0006 (9)	−0.0001 (9)
C6	0.0538 (12)	0.0568 (12)	0.0548 (12)	−0.0287 (10)	0.0027 (9)	0.0059 (9)
O4	0.0412 (7)	0.0460 (7)	0.0356 (7)	−0.0082 (6)	−0.0020 (5)	0.0033 (5)
N4	0.0461 (9)	0.0449 (8)	0.0335 (8)	−0.0129 (7)	−0.0065 (6)	0.0037 (6)
C23	0.0431 (9)	0.0332 (8)	0.0327 (9)	−0.0107 (7)	−0.0086 (7)	0.0016 (7)
O3	0.0472 (8)	0.0618 (9)	0.0393 (7)	0.0047 (7)	−0.0086 (6)	0.0119 (6)
N6	0.0421 (9)	0.0529 (9)	0.0347 (8)	−0.0061 (7)	−0.0042 (7)	0.0083 (7)
C28	0.0441 (10)	0.0437 (10)	0.0357 (9)	−0.0173 (8)	−0.0041 (7)	0.0023 (7)
C15	0.0453 (10)	0.0388 (9)	0.0338 (9)	−0.0055 (8)	−0.0107 (7)	0.0039 (7)
C19	0.0439 (10)	0.0389 (9)	0.0378 (9)	−0.0101 (8)	−0.0125 (8)	0.0028 (7)
N5	0.0406 (8)	0.0531 (9)	0.0433 (9)	−0.0045 (7)	−0.0052 (7)	0.0081 (7)
C26	0.0464 (10)	0.0487 (10)	0.0384 (10)	−0.0063 (8)	−0.0045 (8)	0.0057 (8)
C27	0.0422 (10)	0.0431 (10)	0.0381 (10)	−0.0120 (8)	−0.0031 (8)	0.0024 (8)
C24	0.0417 (10)	0.0454 (10)	0.0472 (11)	−0.0052 (8)	−0.0074 (8)	0.0048 (8)
C22	0.0490 (11)	0.0582 (12)	0.0398 (10)	−0.0161 (9)	0.0006 (8)	0.0003 (9)
C18	0.0552 (12)	0.0573 (12)	0.0346 (10)	−0.0101 (9)	−0.0135 (8)	0.0121 (8)
C20	0.0433 (10)	0.0538 (12)	0.0534 (12)	−0.0067 (9)	−0.0142 (9)	0.0072 (9)
C16	0.0468 (11)	0.0565 (12)	0.0390 (10)	−0.0031 (9)	−0.0022 (8)	0.0006 (8)
C25	0.0458 (11)	0.0512 (11)	0.0435 (11)	−0.0041 (9)	−0.0060 (8)	0.0048 (8)
C17	0.0624 (13)	0.0670 (13)	0.0317 (10)	−0.0107 (10)	−0.0026 (9)	0.0072 (9)
C21	0.0399 (10)	0.0629 (13)	0.0557 (13)	−0.0063 (9)	−0.0033 (9)	0.0024 (10)

Geometric parameters (Å, º)

S1—C14	1.6467 (19)	C6—H6	0.9300
S2—C28	1.6543 (19)	O4—C27	1.353 (2)
O1—C1	1.366 (2)	O4—C28	1.370 (2)
O1—C10	1.438 (2)	N4—C22	1.312 (3)
N1—C8	1.315 (2)	N4—C23	1.361 (2)
N1—C9	1.366 (2)	C23—C19	1.420 (2)
O2—C13	1.367 (2)	C23—C15	1.425 (3)
O2—C14	1.375 (2)	O3—C15	1.366 (2)
C9—C5	1.420 (2)	O3—C24	1.423 (2)
C9—C1	1.428 (2)	N6—C28	1.325 (3)
C1—C2	1.369 (2)	N6—N5	1.392 (2)
N3—C14	1.318 (2)	N6—H29	0.91 (2)
N3—N2	1.388 (2)	C15—C16	1.368 (3)
N3—H1	0.93 (2)	C19—C20	1.410 (3)
C5—C6	1.405 (3)	C19—C18	1.411 (3)
C5—C4	1.412 (3)	N5—C27	1.286 (2)
C2—C3	1.409 (3)	C26—C27	1.489 (2)
C2—H2	0.9300	C26—C25	1.519 (3)
C8—C7	1.397 (3)	C26—H26A	0.9700
C8—H8	0.9300	C26—H26B	0.9700
C3—C4	1.352 (3)	C24—C25	1.522 (3)
C3—H3	0.9300	C24—H24A	0.9700
C13—N2	1.282 (3)	C24—H24B	0.9700
C13—C12	1.483 (3)	C22—C21	1.406 (3)
C4—H4	0.9300	C22—H22	0.9300
C10—C11	1.520 (3)	C18—C17	1.348 (3)
C10—H10A	0.9700	C18—H18	0.9300
C10—H10B	0.9700	C20—C21	1.358 (3)
C12—C11	1.517 (3)	C20—H20	0.9300
C12—H12A	0.9700	C16—C17	1.417 (3)
C12—H12B	0.9700	C16—H16	0.9300
C7—C6	1.359 (3)	C25—H25A	0.9700
C7—H7	0.9300	C25—H25B	0.9700
C11—H11A	0.9700	C17—H17	0.9300
C11—H11B	0.9700	C21—H21	0.9300
C1—O1—C10	116.54 (14)	C27—O4—C28	105.45 (14)
C8—N1—C9	117.63 (15)	C22—N4—C23	118.62 (16)
C13—O2—C14	105.88 (14)	N4—C23—C19	121.71 (17)
N1—C9—C5	121.92 (16)	N4—C23—C15	119.30 (15)
N1—C9—C1	119.43 (15)	C19—C23—C15	118.98 (16)
C5—C9—C1	118.65 (15)	C15—O3—C24	119.38 (15)
O1—C1—C2	125.08 (16)	C28—N6—N5	111.66 (15)
O1—C1—C9	114.95 (15)	C28—N6—H29	125.0 (14)
C2—C1—C9	119.96 (16)	N5—N6—H29	122.8 (14)
C14—N3—N2	112.55 (15)	N6—C28—O4	105.91 (15)
C14—N3—H1	126.5 (15)	N6—C28—S2	130.60 (14)
N2—N3—H1	120.9 (15)	O4—C28—S2	123.47 (14)
C6—C5—C4	122.72 (17)	O3—C15—C16	125.90 (18)
C6—C5—C9	117.59 (17)	O3—C15—C23	113.83 (15)
C4—C5—C9	119.70 (17)	C16—C15—C23	120.27 (16)
C1—C2—C3	120.23 (18)	C20—C19—C18	123.36 (17)
C1—C2—H2	119.9	C20—C19—C23	117.35 (18)
C3—C2—H2	119.9	C18—C19—C23	119.29 (18)
N3—C14—O2	105.17 (15)	C27—N5—N6	102.83 (16)
N3—C14—S1	131.07 (14)	C27—C26—C25	112.40 (16)
O2—C14—S1	123.74 (13)	C27—C26—H26A	109.1
N1—C8—C7	124.37 (17)	C25—C26—H26A	109.1
N1—C8—H8	117.8	C27—C26—H26B	109.1
C7—C8—H8	117.8	C25—C26—H26B	109.1
C4—C3—C2	121.48 (17)	H26A—C26—H26B	107.9
C4—C3—H3	119.3	N5—C27—O4	114.12 (16)
C2—C3—H3	119.3	N5—C27—C26	128.72 (17)
N2—C13—O2	113.04 (16)	O4—C27—C26	117.14 (16)
N2—C13—C12	128.28 (18)	O3—C24—C25	105.42 (16)
O2—C13—C12	118.52 (16)	O3—C24—H24A	110.7
C3—C4—C5	119.94 (17)	C25—C24—H24A	110.7
C3—C4—H4	120.0	O3—C24—H24B	110.7
C5—C4—H4	120.0	C25—C24—H24B	110.7
C13—N2—N3	103.33 (16)	H24A—C24—H24B	108.8
O1—C10—C11	106.91 (15)	N4—C22—C21	123.68 (18)
O1—C10—H10A	110.3	N4—C22—H22	118.2
C11—C10—H10A	110.3	C21—C22—H22	118.2
O1—C10—H10B	110.3	C17—C18—C19	120.17 (17)
C11—C10—H10B	110.3	C17—C18—H18	119.9
H10A—C10—H10B	108.6	C19—C18—H18	119.9
C13—C12—C11	111.70 (17)	C21—C20—C19	120.08 (18)
C13—C12—H12A	109.3	C21—C20—H20	120.0
C11—C12—H12A	109.3	C19—C20—H20	120.0
C13—C12—H12B	109.3	C15—C16—C17	119.53 (19)
C11—C12—H12B	109.3	C15—C16—H16	120.2
H12A—C12—H12B	107.9	C17—C16—H16	120.2
C6—C7—C8	118.71 (18)	C26—C25—C24	111.60 (16)
C6—C7—H7	120.6	C26—C25—H25A	109.3
C8—C7—H7	120.6	C24—C25—H25A	109.3
C12—C11—C10	112.84 (17)	C26—C25—H25B	109.3
C12—C11—H11A	109.0	C24—C25—H25B	109.3
C10—C11—H11A	109.0	H25A—C25—H25B	108.0
C12—C11—H11B	109.0	C18—C17—C16	121.76 (19)
C10—C11—H11B	109.0	C18—C17—H17	119.1
H11A—C11—H11B	107.8	C16—C17—H17	119.1
C7—C6—C5	119.73 (18)	C20—C21—C22	118.56 (19)
C7—C6—H6	120.1	C20—C21—H21	120.7
C5—C6—H6	120.1	C22—C21—H21	120.7
C8—N1—C9—C5	−0.2 (3)	C22—N4—C23—C19	−0.3 (3)
C8—N1—C9—C1	179.16 (16)	C22—N4—C23—C15	−178.87 (17)
C10—O1—C1—C2	12.6 (3)	N5—N6—C28—O4	−2.1 (2)
C10—O1—C1—C9	−165.73 (16)	N5—N6—C28—S2	176.81 (15)
N1—C9—C1—O1	−3.7 (2)	C27—O4—C28—N6	1.71 (19)
C5—C9—C1—O1	175.68 (15)	C27—O4—C28—S2	−177.28 (14)
N1—C9—C1—C2	177.85 (17)	C24—O3—C15—C16	−2.5 (3)
C5—C9—C1—C2	−2.8 (3)	C24—O3—C15—C23	177.99 (16)
N1—C9—C5—C6	1.6 (3)	N4—C23—C15—O3	−2.3 (2)
C1—C9—C5—C6	−177.81 (17)	C19—C23—C15—O3	179.17 (16)
N1—C9—C5—C4	−178.09 (16)	N4—C23—C15—C16	178.20 (18)
C1—C9—C5—C4	2.5 (3)	C19—C23—C15—C16	−0.4 (3)
O1—C1—C2—C3	−176.95 (19)	N4—C23—C19—C20	0.8 (3)
C9—C1—C2—C3	1.3 (3)	C15—C23—C19—C20	179.36 (16)
N2—N3—C14—O2	0.8 (2)	N4—C23—C19—C18	−179.03 (17)
N2—N3—C14—S1	−178.03 (16)	C15—C23—C19—C18	−0.5 (3)
C13—O2—C14—N3	−1.6 (2)	C28—N6—N5—C27	1.6 (2)
C13—O2—C14—S1	177.34 (14)	N6—N5—C27—O4	−0.4 (2)
C9—N1—C8—C7	−2.0 (3)	N6—N5—C27—C26	−178.67 (19)
C1—C2—C3—C4	0.4 (3)	C28—O4—C27—N5	−0.8 (2)
C14—O2—C13—N2	2.0 (2)	C28—O4—C27—C26	177.66 (16)
C14—O2—C13—C12	177.74 (17)	C25—C26—C27—N5	9.2 (3)
C2—C3—C4—C5	−0.6 (3)	C25—C26—C27—O4	−168.98 (17)
C6—C5—C4—C3	179.5 (2)	C15—O3—C24—C25	−175.60 (17)
C9—C5—C4—C3	−0.9 (3)	C23—N4—C22—C21	−0.1 (3)
O2—C13—N2—N3	−1.5 (2)	C20—C19—C18—C17	−178.7 (2)
C12—C13—N2—N3	−176.7 (2)	C23—C19—C18—C17	1.1 (3)
C14—N3—N2—C13	0.4 (2)	C18—C19—C20—C21	179.0 (2)
C1—O1—C10—C11	167.30 (16)	C23—C19—C20—C21	−0.9 (3)
N2—C13—C12—C11	103.3 (3)	O3—C15—C16—C17	−178.9 (2)
O2—C13—C12—C11	−71.7 (2)	C23—C15—C16—C17	0.6 (3)
N1—C8—C7—C6	2.7 (3)	C27—C26—C25—C24	173.48 (17)
C13—C12—C11—C10	−171.58 (16)	O3—C24—C25—C26	−176.73 (17)
O1—C10—C11—C12	72.6 (2)	C19—C18—C17—C16	−0.9 (3)
C8—C7—C6—C5	−1.1 (3)	C15—C16—C17—C18	0.0 (3)
C4—C5—C6—C7	178.8 (2)	C19—C20—C21—C22	0.5 (3)
C9—C5—C6—C7	−0.8 (3)	N4—C22—C21—C20	0.0 (3)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
N3—H1···N4	0.93 (2)	1.84 (2)	2.770 (2)	174 (2)
N3—H1···O3	0.93 (2)	2.54 (2)	3.036 (2)	113.6 (17)
N6—H29···N1^i	0.91 (2)	1.89 (2)	2.782 (2)	165 (2)

Symmetry code: (i) x−1, y, z.