A new linear phenyl­oxazole–benzo­thia­diazole luminophore: crystal growth, structure and fluorescence properties

A new linear luminophore consisting of five conjugated units of oxazole, phenyl­ene and a central benzo­thia­diazole fragment, 4,7-bis­[4-(1,3-oxazol-5-yl)phenyl]-2,1,3-benzo­thia­diazole, has been synthesized and characterized. Needle-like single-crystal samples up to 10 mm in length were obtained by physical vapor transport. The crystal structure was determined at 95 K and 293 K using single-crystal X-ray diffraction. With decreasing temperature, the space group P2₁/n does not change, but the unit-cell volume of the crystal decreases. The presence of intra- and intermolecular hydrogen bonds was established. Melting parameters (T_m = 305.5°C, ΔH_m = 52.2 kJ mol⁻¹) and the presence of a liquid-crystalline mesophase (T_LC = 336.3°C, ΔH_LC = 1.4 kJ mol⁻¹) were determined by differential scanning calorimetry and in situ thermal polarization optical microscopy studies. The presence of linear chains of hydrogen bonds ensures high stability of the crystal structure in a wide temperature range. The luminophore is characterized by a large Stokes shift (5120–5670 cm⁻¹) and a high quantum yield of fluorescence, reaching 96% in solutions (λ_max = 517 nm) and 27% in thin crystalline films (λ_max = 529 nm). The calculated absorption and emission spectra are in good agreement with the experimental data. Because of the excellent optical properties and high thermal stability, the new linear luminophore has great potential for application in organic photonics and optoelectronic devices.

Computing details

For both structures, data collection: CrysAlis PRO 1.171.39.46 (Rigaku OD, 2018); cell refinement: CrysAlis PRO 1.171.39.46 (Rigaku OD, 2018); data reduction: CrysAlis PRO 1.171.39.46 (Rigaku OD, 2018).

(95K)

Crystal data

C24H14N4O2S	F(000) = 872
Mr = 422.5	Dx = 1.552 Mg m^−3
Monoclinic, P21/n	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2yabc	Cell parameters from 3224 reflections
a = 20.6752 (12) Å	θ = 3.6–22.6°
b = 3.7474 (1) Å	µ = 0.21 mm^−1
c = 25.1061 (15) Å	T = 95 K
β = 111.624 (6)°	Plate, translucent light yellow
V = 1808.28 (18) Å^3	0.29 × 0.05 × 0.02 mm
Z = 4

Data collection

Xcalibur, EosS2 with high theta cut diffractometer	2147 independent reflections
Radiation source: X-ray tube	1306 reflections with I > 3σ(I)
Graphite monochromator	Rint = 0.060
Detector resolution: 16.1745 pixels mm^-1	θmax = 23.5°, θmin = 3.4°
ω scans	h = −21→22
Absorption correction: multi-scan CrysAlisPro 1.171.39.46 (Rigaku Oxford Diffraction, 2018) Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm.	k = −4→3
Tmin = 0.877, Tmax = 1	l = −26→26
17668 measured reflections

Refinement

Refinement on F	0 constraints
R[F^2 > 2σ(F^2)] = 0.039	All H-atom parameters refined
wR(F^2) = 0.043	Weighting scheme based on measured s.u.'s w = 1/(σ^2(F) + 0.0001F^2)
S = 1.42	(Δ/σ)max = 0.043
2147 reflections	Δρmax = 0.26 e Å^−3
322 parameters	Δρmin = −0.31 e Å^−3
0 restraints

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

	x	y	z	Uiso*/Ueq
S1	0.42643 (6)	0.3240 (3)	0.03062 (5)	0.0147 (4)
O1	0.15466 (14)	−0.1480 (7)	−0.30284 (12)	0.0147 (13)
O2	0.39425 (15)	0.0529 (7)	0.37569 (13)	0.0216 (14)
N1	0.05381 (19)	0.0278 (8)	−0.36914 (15)	0.0149 (16)
N2	0.35385 (17)	0.2427 (8)	−0.02162 (14)	0.0151 (15)
N3	0.40532 (17)	0.2234 (8)	0.08475 (14)	0.0117 (15)
N4	0.4991 (2)	−0.1441 (9)	0.43317 (15)	0.0209 (17)
C1	0.1112 (2)	0.1780 (11)	−0.18021 (19)	0.0135 (19)
C2	0.1472 (2)	0.0252 (10)	−0.21187 (18)	0.012 (2)
C3	0.4274 (2)	−0.1803 (11)	0.24485 (19)	0.0125 (19)
C4	0.3959 (2)	−0.1587 (11)	0.1857 (2)	0.014 (2)
C5	0.3303 (2)	−0.0073 (10)	0.15949 (18)	0.010 (2)
C6	0.2063 (2)	0.0415 (10)	−0.0918 (2)	0.013 (2)
C7	0.1999 (3)	−0.0415 (10)	0.0053 (2)	0.014 (2)
C8	0.2370 (2)	0.0431 (10)	−0.02835 (19)	0.010 (2)
C9	0.1404 (2)	0.1846 (11)	−0.1209 (2)	0.015 (2)
C10	0.2958 (2)	0.1152 (11)	0.1947 (2)	0.015 (2)
C11	0.1163 (2)	0.0104 (10)	−0.2737 (2)	0.012 (2)
C12	0.0547 (2)	0.1168 (11)	−0.3149 (2)	0.018 (2)
C13	0.2295 (2)	−0.0540 (10)	0.0654 (2)	0.013 (2)
C14	0.3930 (2)	−0.0536 (10)	0.27906 (18)	0.010 (2)
C15	0.2125 (2)	−0.1151 (10)	−0.1829 (2)	0.014 (2)
C16	0.2978 (2)	0.0164 (10)	0.09636 (19)	0.014 (2)
C17	0.4904 (3)	−0.1935 (12)	0.37623 (19)	0.016 (2)
C18	0.3261 (2)	0.0947 (10)	0.2534 (2)	0.013 (2)
C19	0.1131 (2)	−0.1271 (11)	−0.35906 (19)	0.014 (2)
C20	0.4278 (2)	−0.0733 (10)	0.34119 (19)	0.012 (2)
C21	0.2420 (2)	−0.1054 (10)	−0.1239 (2)	0.014 (2)
C22	0.4416 (3)	−0.0015 (13)	0.4299 (2)	0.021 (2)
C23	0.3089 (2)	0.1301 (10)	0.00160 (18)	0.012 (2)
C24	0.3379 (2)	0.1183 (10)	0.06323 (18)	0.012 (2)
H_c19	0.1346 (19)	−0.234 (9)	−0.3878 (17)	0.0183*
H_c12	0.022 (2)	0.272 (12)	−0.306 (2)	0.0445*
H_c15	0.2427 (18)	−0.219 (8)	−0.2033 (15)	0.0022*
H_c1	0.065 (2)	0.284 (9)	−0.2007 (16)	0.0106*
H_c9	0.1173 (18)	0.288 (9)	−0.0945 (16)	0.0092*
H_c21	0.2868 (19)	−0.204 (9)	−0.1068 (15)	0.0028*
H_c7	0.145 (2)	−0.115 (9)	−0.0127 (16)	0.0129*
H_c13	0.1977 (19)	−0.121 (9)	0.0906 (16)	0.0127*
H_c10	0.254 (2)	0.220 (10)	0.1787 (18)	0.0183*
H_c4	0.421 (2)	−0.248 (9)	0.1676 (17)	0.0116*
H_c3	0.4750 (19)	−0.300 (9)	0.2652 (15)	0.006*
H_c18	0.306 (2)	0.193 (11)	0.283 (2)	0.0379*
H_c17	0.527 (2)	−0.319 (11)	0.3700 (18)	0.0289*
H_c22	0.4304 (19)	0.077 (9)	0.4559 (17)	0.0003*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
S1	0.0109 (7)	0.0223 (6)	0.0106 (7)	−0.0029 (5)	0.0036 (5)	−0.0003 (5)
O1	0.0129 (17)	0.0188 (16)	0.013 (2)	0.0027 (14)	0.0048 (17)	0.0001 (14)
O2	0.017 (2)	0.0330 (19)	0.010 (2)	0.0056 (14)	−0.0009 (19)	0.0017 (14)
N1	0.018 (3)	0.0171 (19)	0.008 (3)	0.0019 (18)	0.0035 (19)	−0.0032 (17)
N2	0.018 (2)	0.015 (2)	0.011 (2)	−0.0035 (16)	0.004 (2)	0.0013 (15)
N3	0.013 (2)	0.016 (2)	0.009 (2)	−0.0011 (16)	0.0076 (18)	0.0009 (15)
N4	0.021 (3)	0.028 (2)	0.015 (3)	0.003 (2)	0.007 (2)	−0.0021 (18)
C1	0.017 (3)	0.012 (2)	0.005 (3)	−0.002 (2)	−0.003 (3)	0.000 (2)
C2	0.016 (3)	0.009 (2)	0.007 (3)	−0.0010 (19)	−0.001 (3)	0.0000 (19)
C3	0.014 (3)	0.012 (2)	0.011 (3)	0.000 (2)	0.005 (2)	0.005 (2)
C4	0.015 (3)	0.011 (2)	0.017 (4)	−0.003 (2)	0.009 (3)	−0.002 (2)
C5	0.010 (3)	0.012 (2)	0.007 (3)	−0.0032 (19)	0.002 (3)	−0.0001 (19)
C6	0.008 (3)	0.009 (2)	0.020 (3)	−0.0066 (19)	0.004 (3)	−0.001 (2)
C7	0.015 (3)	0.013 (2)	0.016 (3)	−0.0011 (19)	0.009 (3)	0.0035 (19)
C8	0.010 (3)	0.013 (2)	0.009 (3)	0.0019 (19)	0.003 (3)	0.0020 (19)
C9	0.015 (3)	0.011 (2)	0.021 (4)	−0.003 (2)	0.008 (3)	−0.002 (2)
C10	0.012 (3)	0.014 (3)	0.020 (4)	0.001 (2)	0.007 (3)	0.002 (2)
C11	0.010 (3)	0.012 (2)	0.019 (4)	−0.002 (2)	0.010 (3)	−0.002 (2)
C12	0.020 (3)	0.011 (3)	0.018 (3)	0.002 (2)	0.002 (3)	−0.002 (2)
C13	0.011 (3)	0.013 (3)	0.015 (3)	0.0009 (19)	0.004 (3)	0.0010 (19)
C14	0.014 (3)	0.010 (2)	0.010 (3)	−0.0066 (19)	0.009 (3)	−0.0028 (19)
C15	0.010 (3)	0.011 (2)	0.022 (4)	−0.003 (2)	0.009 (3)	−0.002 (2)
C16	0.017 (3)	0.007 (2)	0.012 (3)	0.0016 (19)	−0.001 (3)	0.000 (2)
C17	0.022 (3)	0.021 (3)	0.011 (3)	0.001 (2)	0.011 (3)	−0.002 (2)
C18	0.020 (3)	0.010 (3)	0.009 (3)	−0.003 (2)	0.007 (3)	0.001 (2)
C19	0.018 (3)	0.018 (2)	0.004 (3)	−0.004 (2)	0.002 (3)	0.001 (2)
C20	0.013 (3)	0.012 (3)	0.014 (3)	0.0019 (19)	0.009 (3)	−0.004 (2)
C21	0.013 (3)	0.013 (3)	0.014 (3)	0.000 (2)	0.003 (3)	0.001 (2)
C22	0.024 (4)	0.035 (3)	0.008 (4)	0.002 (2)	0.010 (3)	−0.001 (2)
C23	0.012 (3)	0.010 (2)	0.012 (3)	−0.002 (2)	0.003 (3)	0.002 (2)
C24	0.012 (3)	0.012 (2)	0.008 (3)	0.000 (2)	0.000 (2)	0.0004 (19)

Geometric parameters (Å, º)

S1—N2	1.617 (3)	C6—C8	1.482 (6)
S1—N3	1.618 (4)	C6—C9	1.395 (6)
S1—C23	2.380 (4)	C6—C15	2.409 (8)
S1—C24	2.391 (5)	C6—C21	1.390 (8)
O1—N1	2.235 (4)	C6—H_c9	2.04 (4)
O1—C2	2.433 (6)	C6—H_c21	2.05 (4)
O1—C11	1.394 (6)	C7—C8	1.371 (8)
O1—C12	2.210 (6)	C7—C13	1.404 (6)
O1—C19	1.358 (5)	C7—C16	2.440 (6)
O1—H_c19	2.04 (4)	C7—C23	2.377 (7)
O2—N4	2.241 (4)	C7—H_c7	1.09 (4)
O2—C14	2.450 (6)	C7—H_c13	2.18 (4)
O2—C17	2.188 (6)	C8—C13	2.442 (7)
O2—C20	1.378 (7)	C8—C23	1.434 (6)
O2—C22	1.367 (5)	C8—C24	2.487 (5)
O2—H_c18	2.42 (4)	C8—H_c7	2.16 (5)
O2—H_c22	1.87 (4)	C9—C21	2.391 (7)
N1—C11	2.265 (5)	C9—H_c1	2.07 (3)
N1—C12	1.395 (7)	C9—H_c9	1.02 (4)
N1—C19	1.294 (6)	C10—C14	2.406 (6)
N1—H_c19	2.13 (4)	C10—C18	1.373 (7)
N1—H_c12	2.14 (5)	C10—H_c10	0.89 (4)
N2—N3	2.485 (5)	C10—H_c18	2.17 (5)
N2—C8	2.475 (6)	C11—C12	1.370 (6)
N2—C23	1.335 (7)	C11—C15	2.456 (6)
N2—C24	2.319 (6)	C11—C19	2.181 (7)
N2—H_c19^i	2.37 (5)	C11—H_c12	2.07 (4)
N3—C16	2.471 (7)	C12—C19	2.123 (8)
N3—C23	2.321 (5)	C12—H_c12	0.99 (5)
N3—C24	1.354 (5)	C13—C16	1.363 (6)
N4—C17	1.386 (6)	C13—C24	2.352 (7)
N4—C20	2.251 (5)	C13—H_c7	2.10 (3)
N4—C22	1.278 (7)	C13—H_c13	1.10 (5)
N4—H_c17	1.98 (5)	C14—C18	1.409 (6)
N4—H_c22	1.90 (4)	C14—C20	1.459 (6)
C1—C2	1.396 (8)	C14—H_c3	2.07 (4)
C1—C6	2.416 (5)	C14—H_c18	2.05 (5)
C1—C9	1.385 (6)	C15—C21	1.380 (7)
C1—C11	2.469 (7)	C15—H_c15	1.02 (4)
C1—C15	2.387 (7)	C15—H_c21	1.99 (3)
C1—H_c1	0.98 (4)	C16—C24	1.427 (8)
C1—H_c9	2.15 (4)	C16—H_c13	2.09 (4)
C2—C9	2.414 (7)	C17—C20	1.346 (6)
C2—C11	1.446 (6)	C17—C22	2.086 (8)
C2—C15	1.380 (6)	C17—H_c17	0.94 (5)
C2—C21	2.403 (5)	C18—H_c10	1.97 (4)
C2—H_c15	2.11 (4)	C18—H_c18	1.05 (5)
C2—H_c1	2.06 (4)	C19—H_c19	1.06 (5)
C3—C4	1.386 (6)	C20—C22	2.155 (7)
C3—C5	2.424 (5)	C20—H_c17	2.11 (4)
C3—C14	1.385 (8)	C21—H_c15	2.04 (4)
C3—C18	2.414 (7)	C21—H_c21	0.94 (3)
C3—C20	2.449 (7)	C22—H_c22	0.82 (5)
C3—H_c4	1.91 (4)	C23—C24	1.439 (6)
C3—H_c3	1.03 (3)	H_c19—H_c21^ii	2.43 (5)
C4—C5	1.392 (6)	H_c12—H_c1	2.46 (6)
C4—C10	2.395 (7)	H_c15—H_c21	2.25 (5)
C4—C14	2.398 (7)	H_c1—H_c9	2.48 (5)
C4—C16	2.495 (6)	H_c9—H_c7	2.44 (5)
C4—H_c4	0.87 (5)	H_c9—H_c17^iii	2.49 (5)
C4—H_c3	2.13 (3)	H_c7—H_c13	2.41 (5)
C5—C10	1.402 (8)	H_c13—H_c10	2.45 (5)
C5—C16	1.479 (6)	H_c10—H_c18	2.45 (6)
C5—C18	2.421 (7)	H_c4—H_c3	2.30 (5)
C5—H_c10	2.00 (5)	H_c3—H_c17	2.45 (5)
C5—H_c4	2.02 (4)
N2—S1—N3	100.39 (19)	C11—C12—C19	73.8 (3)
N2—S1—C23	32.44 (18)	C11—C12—H_c12	122 (2)
N2—S1—C24	67.56 (18)	C19—C12—H_c12	162 (3)
N3—S1—C23	67.95 (16)	C7—C13—C8	28.0 (3)
N3—S1—C24	32.83 (14)	C7—C13—C16	123.8 (5)
C23—S1—C24	35.12 (14)	C7—C13—C24	90.5 (4)
N1—O1—C2	104.83 (19)	C7—C13—H_c7	28.2 (13)
N1—O1—C11	73.1 (2)	C7—C13—H_c13	120.7 (17)
N1—O1—C12	36.59 (17)	C8—C13—C16	95.8 (4)
N1—O1—C19	31.7 (3)	C8—C13—C24	62.5 (2)
N1—O1—H_c19	59.6 (11)	C8—C13—H_c7	56.2 (13)
C2—O1—C11	31.7 (2)	C8—C13—H_c13	148.7 (17)
C2—O1—C12	68.24 (18)	C16—C13—C24	33.4 (3)
C2—O1—C19	136.5 (3)	C16—C13—H_c7	152.0 (14)
C2—O1—H_c19	164.4 (11)	C16—C13—H_c13	115.4 (17)
C11—O1—C12	36.6 (2)	C24—C13—H_c7	118.6 (13)
C11—O1—C19	104.8 (3)	C24—C13—H_c13	148.8 (17)
C11—O1—H_c19	132.8 (11)	H_c7—C13—H_c13	93 (2)
C12—O1—C19	68.3 (3)	O2—C14—C3	148.2 (3)
C12—O1—H_c19	96.2 (11)	O2—C14—C4	178.1 (2)
C19—O1—H_c19	27.9 (11)	O2—C14—C10	121.9 (3)
N4—O2—C14	103.8 (2)	O2—C14—C18	92.2 (3)
N4—O2—C17	36.45 (17)	O2—C14—C20	29.4 (2)
N4—O2—C20	72.5 (2)	O2—C14—H_c3	122.0 (9)
N4—O2—C22	30.9 (3)	O2—C14—H_c18	64.2 (13)
N4—O2—H_c18	153.6 (13)	C3—C14—C4	30.1 (2)
N4—O2—H_c22	54.3 (12)	C3—C14—C10	89.9 (3)
C14—O2—C17	67.35 (18)	C3—C14—C18	119.6 (4)
C14—O2—C20	31.3 (2)	C3—C14—C20	118.8 (4)
C14—O2—C22	134.7 (3)	C3—C14—H_c3	26.3 (10)
C14—O2—H_c18	49.9 (13)	C3—C14—H_c18	147.5 (13)
C14—O2—H_c22	157.9 (13)	C4—C14—C10	59.8 (2)
C17—O2—C20	36.1 (2)	C4—C14—C18	89.5 (3)
C17—O2—C22	67.3 (3)	C4—C14—C20	148.9 (4)
C17—O2—H_c18	117.2 (13)	C4—C14—H_c3	56.3 (9)
C17—O2—H_c22	90.7 (12)	C4—C14—H_c18	117.5 (13)
C20—O2—C22	103.4 (4)	C10—C14—C18	29.7 (3)
C20—O2—H_c18	81.2 (13)	C10—C14—C20	151.3 (4)
C20—O2—H_c22	126.7 (13)	C10—C14—H_c3	116.1 (10)
C22—O2—H_c18	174.9 (12)	C10—C14—H_c18	57.7 (13)
C22—O2—H_c22	23.4 (12)	C18—C14—C20	121.6 (5)
H_c18—O2—H_c22	151.8 (17)	C18—C14—H_c3	145.8 (10)
O1—N1—C11	36.09 (16)	C18—C14—H_c18	28.0 (13)
O1—N1—C12	70.7 (2)	C20—C14—H_c3	92.6 (10)
O1—N1—C19	33.4 (2)	C20—C14—H_c18	93.6 (13)
O1—N1—H_c19	55.7 (10)	H_c3—C14—H_c18	173.8 (16)
O1—N1—H_c12	91.9 (11)	C1—C15—C2	30.9 (3)
C11—N1—C12	34.6 (2)	C1—C15—C6	60.48 (19)
C11—N1—C19	69.5 (3)	C1—C15—C11	61.28 (19)
C11—N1—H_c19	91.8 (10)	C1—C15—C21	90.2 (4)
C11—N1—H_c12	55.9 (11)	C1—C15—H_c15	153.6 (17)
C12—N1—C19	104.2 (3)	C1—C15—H_c21	115.2 (13)
C12—N1—H_c19	126.5 (10)	C2—C15—C6	91.4 (3)
C12—N1—H_c12	21.6 (11)	C2—C15—C11	30.4 (3)
C19—N1—H_c19	22.3 (10)	C2—C15—C21	121.1 (5)
C19—N1—H_c12	125.3 (11)	C2—C15—H_c15	122.8 (17)
H_c19—N1—H_c12	147.4 (14)	C2—C15—H_c21	146.1 (13)
S1—N2—N3	39.81 (13)	C6—C15—C11	121.8 (3)
S1—N2—C8	134.7 (2)	C6—C15—C21	29.7 (3)
S1—N2—C23	107.0 (3)	C6—C15—H_c15	145.8 (17)
S1—N2—C24	72.32 (17)	C6—C15—H_c21	54.7 (13)
S1—N2—H_c19^i	112.3 (9)	C11—C15—C21	151.5 (4)
N3—N2—C8	94.89 (19)	C11—C15—H_c15	92.4 (17)
N3—N2—C23	67.2 (2)	C11—C15—H_c21	176.5 (13)
N3—N2—C24	32.51 (14)	C21—C15—H_c15	116.1 (17)
N3—N2—H_c19^i	151.1 (9)	C21—C15—H_c21	25.0 (13)
C8—N2—C23	27.7 (2)	H_c15—C15—H_c21	91 (2)
C8—N2—C24	62.39 (17)	N3—C16—C4	73.74 (19)
C8—N2—H_c19^i	112.7 (9)	N3—C16—C5	94.2 (3)
C23—N2—C24	34.7 (2)	N3—C16—C7	112.9 (3)
C23—N2—H_c19^i	139.7 (9)	N3—C16—C13	141.3 (4)
C24—N2—H_c19^i	170.2 (9)	N3—C16—C24	26.52 (19)
S1—N3—N2	39.80 (12)	N3—C16—H_c13	169.2 (10)
S1—N3—C16	134.86 (19)	C4—C16—C5	28.7 (2)
S1—N3—C23	71.82 (17)	C4—C16—C7	159.6 (2)
S1—N3—C24	106.8 (3)	C4—C16—C13	142.2 (4)
N2—N3—C16	95.07 (17)	C4—C16—C24	98.0 (3)
N2—N3—C23	32.03 (16)	C4—C16—H_c13	117.0 (10)
N2—N3—C24	67.0 (2)	C5—C16—C7	153.0 (4)
C16—N3—C23	63.05 (18)	C5—C16—C13	124.5 (5)
C16—N3—C24	28.1 (2)	C5—C16—C24	120.6 (4)
C23—N3—C24	35.0 (3)	C5—C16—H_c13	96.1 (11)
O2—N4—C17	69.7 (3)	C7—C16—C13	28.5 (3)
O2—N4—C20	35.73 (17)	C7—C16—C24	86.4 (3)
O2—N4—C22	33.3 (3)	C7—C16—H_c13	56.9 (11)
O2—N4—H_c17	95.0 (11)	C13—C16—C24	114.9 (4)
O2—N4—H_c22	53.0 (11)	C13—C16—H_c13	28.4 (11)
C17—N4—C20	34.0 (3)	C24—C16—H_c13	143.3 (11)
C17—N4—C22	103.0 (4)	O2—C17—N4	73.9 (3)
C17—N4—H_c17	25.5 (11)	O2—C17—C20	37.1 (3)
C17—N4—H_c22	122.7 (11)	O2—C17—C22	37.21 (18)
C20—N4—C22	69.0 (3)	O2—C17—H_c17	169 (2)
C20—N4—H_c17	59.4 (11)	N4—C17—C20	110.9 (5)
C20—N4—H_c22	88.7 (11)	N4—C17—C22	36.7 (2)
C22—N4—H_c17	128.3 (11)	N4—C17—H_c17	115 (2)
C22—N4—H_c22	19.8 (11)	C20—C17—C22	74.3 (4)
H_c17—N4—H_c22	148.1 (15)	C20—C17—H_c17	133 (2)
C2—C1—C6	90.7 (3)	C22—C17—H_c17	152 (3)
C2—C1—C9	120.5 (4)	C3—C18—C5	60.18 (19)
C2—C1—C11	30.2 (2)	C3—C18—C10	89.8 (4)
C2—C1—C15	30.5 (2)	C3—C18—C14	29.9 (3)
C2—C1—H_c1	119 (3)	C3—C18—H_c10	113.1 (15)
C2—C1—H_c9	143.3 (10)	C3—C18—H_c18	143 (2)
C6—C1—C9	29.8 (3)	C5—C18—C10	29.6 (3)
C6—C1—C11	120.9 (3)	C5—C18—C14	90.1 (3)
C6—C1—C15	60.2 (2)	C5—C18—H_c10	52.9 (15)
C6—C1—H_c1	150 (3)	C5—C18—H_c18	157 (2)
C6—C1—H_c9	52.6 (9)	C10—C18—C14	119.7 (5)
C9—C1—C11	150.7 (4)	C10—C18—H_c10	23.3 (15)
C9—C1—C15	90.0 (3)	C10—C18—H_c18	127 (2)
C9—C1—H_c1	121 (3)	C14—C18—H_c10	143.0 (15)
C9—C1—H_c9	22.9 (9)	C14—C18—H_c18	113 (2)
C11—C1—C15	60.7 (2)	H_c10—C18—H_c18	104 (3)
C11—C1—H_c1	89 (3)	O1—C19—N1	114.9 (4)
C11—C1—H_c9	173.5 (9)	O1—C19—C11	38.2 (2)
C15—C1—H_c1	149 (3)	O1—C19—C12	75.3 (3)
C15—C1—H_c9	112.8 (9)	O1—C19—H_c19	115.1 (18)
H_c1—C1—H_c9	98 (3)	N1—C19—C11	76.7 (3)
O1—C2—C1	151.1 (3)	N1—C19—C12	39.6 (3)
O1—C2—C9	178.8 (2)	N1—C19—H_c19	130.0 (18)
O1—C2—C11	30.4 (2)	C11—C19—C12	37.10 (18)
O1—C2—C15	90.3 (3)	C11—C19—H_c19	153.3 (18)
O1—C2—C21	119.8 (2)	C12—C19—H_c19	169.6 (18)
O1—C2—H_c15	66.4 (10)	O2—C20—N4	71.7 (2)
O1—C2—H_c1	126.4 (10)	O2—C20—C3	149.1 (3)
C1—C2—C9	29.6 (2)	O2—C20—C14	119.4 (4)
C1—C2—C11	120.7 (4)	O2—C20—C17	106.8 (4)
C1—C2—C15	118.6 (4)	O2—C20—C22	38.1 (2)
C1—C2—C21	89.2 (3)	O2—C20—H_c17	125.6 (13)
C1—C2—H_c15	142.5 (10)	N4—C20—C3	139.2 (3)
C1—C2—H_c1	24.7 (10)	N4—C20—C14	168.9 (4)
C9—C2—C11	150.3 (4)	N4—C20—C17	35.1 (3)
C9—C2—C15	89.0 (3)	N4—C20—C22	33.64 (19)
C9—C2—C21	59.52 (19)	N4—C20—H_c17	53.9 (13)
C9—C2—H_c15	112.9 (10)	C3—C20—C14	29.7 (2)
C9—C2—H_c1	54.3 (10)	C3—C20—C17	104.1 (4)
C11—C2—C15	120.7 (5)	C3—C20—C22	172.8 (3)
C11—C2—C21	150.2 (4)	C3—C20—H_c17	85.3 (13)
C11—C2—H_c15	96.8 (10)	C14—C20—C17	133.8 (5)
C11—C2—H_c1	96.0 (10)	C14—C20—C22	157.5 (4)
C15—C2—C21	29.5 (3)	C14—C20—H_c17	115.0 (13)
C15—C2—H_c15	23.9 (10)	C17—C20—C22	68.7 (3)
C15—C2—H_c1	143.3 (11)	C17—C20—H_c17	18.9 (13)
C21—C2—H_c15	53.4 (10)	C22—C20—H_c17	87.5 (13)
C21—C2—H_c1	113.9 (10)	C2—C21—C6	91.4 (3)
H_c15—C2—H_c1	167.1 (14)	C2—C21—C9	60.5 (2)
C4—C3—C5	29.3 (3)	C2—C21—C15	29.5 (3)
C4—C3—C14	119.9 (4)	C2—C21—H_c15	56.1 (9)
C4—C3—C18	89.4 (3)	C2—C21—H_c21	146 (3)
C4—C3—C20	151.3 (4)	C6—C21—C9	30.9 (2)
C4—C3—H_c4	24.7 (12)	C6—C21—C15	120.8 (4)
C4—C3—H_c3	123 (2)	C6—C21—H_c15	147.4 (10)
C5—C3—C14	90.5 (3)	C6—C21—H_c21	122 (3)
C5—C3—C18	60.05 (19)	C9—C21—C15	89.9 (3)
C5—C3—C20	122.0 (3)	C9—C21—H_c15	116.5 (9)
C5—C3—H_c4	54.0 (12)	C9—C21—H_c21	153 (3)
C5—C3—H_c3	152 (2)	C15—C21—H_c15	26.6 (9)
C14—C3—C18	30.5 (2)	C15—C21—H_c21	117 (3)
C14—C3—C20	31.5 (2)	H_c15—C21—H_c21	90 (3)
C14—C3—H_c4	144.5 (12)	O2—C22—N4	115.8 (5)
C14—C3—H_c3	117 (2)	O2—C22—C17	75.4 (3)
C18—C3—C20	62.0 (2)	O2—C22—C20	38.5 (3)
C18—C3—H_c4	114.0 (12)	O2—C22—H_c22	115 (2)
C18—C3—H_c3	148 (2)	N4—C22—C17	40.3 (3)
C20—C3—H_c4	176.0 (12)	N4—C22—C20	77.3 (3)
C20—C3—H_c3	86 (2)	N4—C22—H_c22	129 (2)
H_c4—C3—H_c3	98 (3)	C17—C22—C20	36.98 (19)
C3—C4—C5	121.4 (5)	C17—C22—H_c22	168 (2)
C3—C4—C10	90.3 (4)	C20—C22—H_c22	154 (2)
C3—C4—C14	30.0 (3)	S1—C23—N2	40.52 (17)
C3—C4—C16	152.1 (4)	S1—C23—N3	40.23 (12)
C3—C4—H_c4	114 (2)	S1—C23—C7	161.2 (2)
C3—C4—H_c3	24.0 (12)	S1—C23—C8	167.0 (4)
C5—C4—C10	31.2 (3)	S1—C23—C24	72.9 (2)
C5—C4—C14	91.4 (3)	N2—C23—N3	80.7 (2)
C5—C4—C16	30.6 (3)	N2—C23—C7	157.7 (3)
C5—C4—H_c4	125 (2)	N2—C23—C8	126.6 (4)
C5—C4—H_c3	145.4 (12)	N2—C23—C24	113.4 (4)
C10—C4—C14	60.3 (2)	N3—C23—C7	121.2 (3)
C10—C4—C16	61.8 (2)	N3—C23—C8	152.5 (4)
C10—C4—H_c4	156 (2)	N3—C23—C24	32.6 (2)
C10—C4—H_c3	114.2 (12)	C7—C23—C8	31.3 (3)
C14—C4—C16	122.1 (3)	C7—C23—C24	88.6 (3)
C14—C4—H_c4	144 (2)	C8—C23—C24	119.9 (5)
C14—C4—H_c3	54.0 (12)	S1—C24—N2	40.12 (12)
C16—C4—H_c4	94 (2)	S1—C24—N3	40.4 (2)
C16—C4—H_c3	176.0 (12)	S1—C24—C8	102.0 (2)
H_c4—C4—H_c3	90 (3)	S1—C24—C13	162.2 (2)
C3—C5—C4	29.2 (3)	S1—C24—C16	165.7 (3)
C3—C5—C10	88.7 (3)	S1—C24—C23	72.0 (3)
C3—C5—C16	149.9 (4)	N2—C24—N3	80.5 (3)
C3—C5—C18	59.78 (19)	N2—C24—C8	61.86 (18)
C3—C5—H_c10	111.7 (11)	N2—C24—C13	122.4 (2)
C3—C5—H_c4	49.9 (12)	N2—C24—C16	154.0 (3)
C4—C5—C10	117.9 (4)	N2—C24—C23	31.9 (2)
C4—C5—C16	120.7 (5)	N3—C24—C8	142.3 (4)
C4—C5—C18	89.0 (3)	N3—C24—C13	156.9 (4)
C4—C5—H_c10	140.9 (12)	N3—C24—C16	125.4 (4)
C4—C5—H_c4	20.7 (12)	N3—C24—C23	112.4 (4)
C10—C5—C16	121.4 (4)	C8—C24—C13	60.53 (19)
C10—C5—C18	29.0 (2)	C8—C24—C16	92.2 (3)
C10—C5—H_c10	23.0 (11)	C8—C24—C23	30.0 (2)
C10—C5—H_c4	138.6 (12)	C13—C24—C16	31.7 (2)
C16—C5—C18	150.4 (4)	C13—C24—C23	90.5 (3)
C16—C5—H_c10	98.4 (11)	C16—C24—C23	122.2 (4)
C16—C5—H_c4	99.9 (12)	O1—H_c19—N1	64.7 (14)
C18—C5—H_c10	51.9 (11)	O1—H_c19—N2^ii	162 (2)
C18—C5—H_c4	109.7 (12)	O1—H_c19—C19	37.0 (13)
H_c10—C5—H_c4	161.6 (16)	O1—H_c19—H_c21^ii	106.8 (16)
C1—C6—C8	150.2 (4)	N1—H_c19—N2^ii	126.2 (15)
C1—C6—C9	29.6 (3)	N1—H_c19—C19	27.7 (12)
C1—C6—C15	59.32 (19)	N1—H_c19—H_c21^ii	160 (2)
C1—C6—C21	88.8 (3)	N2^ii—H_c19—C19	152 (3)
C1—C6—H_c9	56.9 (11)	N2^ii—H_c19—H_c21^ii	67.4 (15)
C1—C6—H_c21	111.5 (10)	C19—H_c19—H_c21^ii	140 (3)
C8—C6—C9	120.7 (5)	N1—H_c12—C11	65.1 (15)
C8—C6—C15	150.4 (3)	N1—H_c12—C12	31.3 (19)
C8—C6—C21	121.0 (4)	N1—H_c12—H_c1	136 (2)
C8—C6—H_c9	93.3 (11)	C11—H_c12—C12	34.2 (15)
C8—C6—H_c21	98.3 (10)	C11—H_c12—H_c1	70.7 (15)
C9—C6—C15	88.9 (3)	C12—H_c12—H_c1	104 (3)
C9—C6—C21	118.3 (4)	C2—H_c15—C15	33.3 (11)
C9—C6—H_c9	27.4 (11)	C2—H_c15—C21	70.6 (13)
C9—C6—H_c21	141.0 (10)	C2—H_c15—H_c21	95.3 (19)
C15—C6—C21	29.5 (2)	C15—H_c15—C21	37.3 (13)
C15—C6—H_c9	116.2 (11)	C15—H_c15—H_c21	62 (2)
C15—C6—H_c21	52.2 (10)	C21—H_c15—H_c21	24.7 (11)
C21—C6—H_c9	145.7 (11)	C1—H_c1—C2	36.3 (18)
C21—C6—H_c21	22.7 (10)	C1—H_c1—C9	35.2 (16)
H_c9—C6—H_c21	168.4 (14)	C1—H_c1—H_c12	117 (4)
C8—C7—C13	123.3 (4)	C1—H_c1—H_c9	59 (2)
C8—C7—C16	95.6 (3)	C2—H_c1—C9	71.6 (12)
C8—C7—C23	32.9 (2)	C2—H_c1—H_c12	80.7 (19)
C8—C7—H_c7	122 (2)	C2—H_c1—H_c9	95.5 (15)
C8—C7—H_c13	148.9 (10)	C9—H_c1—H_c12	152 (3)
C13—C7—C16	27.6 (3)	C9—H_c1—H_c9	23.9 (10)
C13—C7—C23	90.4 (3)	H_c12—H_c1—H_c9	176 (3)
C13—C7—H_c7	114 (2)	C1—H_c9—C6	70.4 (14)
C13—C7—H_c13	25.7 (10)	C1—H_c9—C9	31.7 (13)
C16—C7—C23	62.8 (2)	C1—H_c9—H_c1	23.2 (10)
C16—C7—H_c7	142 (2)	C1—H_c9—H_c7	129.2 (18)
C16—C7—H_c13	53.3 (10)	C1—H_c9—H_c17^iii	75.3 (15)
C23—C7—H_c7	155 (2)	C6—H_c9—C9	38.8 (13)
C23—C7—H_c13	116.1 (10)	C6—H_c9—H_c1	93.6 (19)
H_c7—C7—H_c13	89 (2)	C6—H_c9—H_c7	76.2 (15)
N2—C8—C6	95.4 (3)	C6—H_c9—H_c17^iii	104.1 (18)
N2—C8—C7	141.4 (3)	C9—H_c9—H_c1	54.9 (19)
N2—C8—C13	112.7 (2)	C9—H_c9—H_c7	107 (2)
N2—C8—C23	25.7 (2)	C9—H_c9—H_c17^iii	88 (2)
N2—C8—C24	55.74 (17)	H_c1—H_c9—H_c7	140.8 (18)
N2—C8—H_c7	166.5 (9)	H_c1—H_c9—H_c17^iii	68.8 (16)
C6—C8—C7	123.2 (4)	H_c7—H_c9—H_c17^iii	77.0 (16)
C6—C8—C13	151.8 (4)	C6—H_c21—C15	73.1 (12)
C6—C8—C23	121.0 (5)	C6—H_c21—C21	34.8 (18)
C6—C8—C24	151.1 (4)	C6—H_c21—H_c19^i	106.8 (17)
C6—C8—H_c7	97.9 (9)	C6—H_c21—H_c15	100.0 (16)
C7—C8—C13	28.7 (2)	C15—H_c21—C21	38.3 (15)
C7—C8—C23	115.8 (4)	C15—H_c21—H_c19^i	97.0 (17)
C7—C8—C24	85.7 (3)	C15—H_c21—H_c15	26.9 (11)
C7—C8—H_c7	25.2 (9)	C21—H_c21—H_c19^i	105 (3)
C13—C8—C23	87.1 (3)	C21—H_c21—H_c15	65 (2)
C13—C8—C24	57.00 (19)	H_c19^i—H_c21—H_c15	88.4 (19)
C13—C8—H_c7	53.9 (9)	C7—H_c7—C8	32.4 (16)
C23—C8—C24	30.1 (3)	C7—H_c7—C13	37.5 (13)
C23—C8—H_c7	141.1 (10)	C7—H_c7—H_c9	94 (3)
C24—C8—H_c7	110.9 (9)	C7—H_c7—H_c13	64 (2)
C1—C9—C2	29.9 (3)	C8—H_c7—C13	69.9 (12)
C1—C9—C6	120.7 (5)	C8—H_c7—H_c9	68.1 (15)
C1—C9—C21	89.9 (4)	C8—H_c7—H_c13	96.9 (16)
C1—C9—H_c1	24.2 (13)	C13—H_c7—H_c9	125.0 (18)
C1—C9—H_c9	125.5 (18)	C13—H_c7—H_c13	27.0 (11)
C2—C9—C6	90.8 (3)	H_c9—H_c7—H_c13	141.5 (18)
C2—C9—C21	60.0 (2)	C7—H_c13—C13	33.6 (12)
C2—C9—H_c1	54.1 (13)	C7—H_c13—C16	69.8 (14)
C2—C9—H_c9	155.3 (18)	C7—H_c13—H_c7	26.8 (12)
C6—C9—C21	30.8 (3)	C7—H_c13—H_c10	130 (2)
C6—C9—H_c1	144.9 (13)	C13—H_c13—C16	36.2 (12)
C6—C9—H_c9	113.9 (18)	C13—H_c13—H_c7	60 (2)
C21—C9—H_c1	114.1 (13)	C13—H_c13—H_c10	102 (2)
C21—C9—H_c9	144.7 (18)	C16—H_c13—H_c7	97 (2)
H_c1—C9—H_c9	101 (2)	C16—H_c13—H_c10	71.2 (15)
C4—C10—C5	30.9 (2)	H_c7—H_c13—H_c10	147 (2)
C4—C10—C14	59.9 (2)	C5—H_c10—C10	38 (2)
C4—C10—C18	90.5 (3)	C5—H_c10—C18	75.2 (14)
C4—C10—H_c10	150 (3)	C5—H_c10—H_c13	73.4 (17)
C4—C10—H_c18	112.9 (11)	C5—H_c10—H_c18	99.7 (18)
C5—C10—C14	90.8 (3)	C10—H_c10—C18	37.4 (19)
C5—C10—C18	121.4 (4)	C10—H_c10—H_c13	104 (3)
C5—C10—H_c10	119 (3)	C10—H_c10—H_c18	62 (3)
C5—C10—H_c18	143.8 (12)	C18—H_c10—H_c13	133 (2)
C14—C10—C18	30.6 (3)	C18—H_c10—H_c18	24.5 (13)
C14—C10—H_c10	150 (3)	H_c13—H_c10—H_c18	145 (2)
C14—C10—H_c18	53.0 (11)	C3—H_c4—C4	41.6 (18)
C18—C10—H_c10	119 (3)	C3—H_c4—C5	76.1 (17)
C18—C10—H_c18	22.5 (11)	C3—H_c4—H_c3	26.3 (11)
H_c10—C10—H_c18	97 (3)	C4—H_c4—C5	34.5 (16)
O1—C11—N1	70.8 (2)	C4—H_c4—H_c3	68 (3)
O1—C11—C1	147.0 (3)	C5—H_c4—H_c3	102 (2)
O1—C11—C2	117.9 (4)	C3—H_c3—C4	33.2 (14)
O1—C11—C12	106.1 (4)	C3—H_c3—C14	36.6 (17)
O1—C11—C15	89.0 (2)	C3—H_c3—H_c4	55 (2)
O1—C11—C19	37.0 (2)	C3—H_c3—H_c17	120 (3)
O1—C11—H_c12	129.5 (15)	C4—H_c3—C14	69.7 (11)
N1—C11—C1	142.3 (3)	C4—H_c3—H_c4	22.3 (12)
N1—C11—C2	171.3 (4)	C4—H_c3—H_c17	153 (2)
N1—C11—C12	35.4 (3)	C14—H_c3—H_c4	92.0 (16)
N1—C11—C15	159.8 (3)	C14—H_c3—H_c17	83.8 (18)
N1—C11—C19	33.77 (17)	H_c4—H_c3—H_c17	175 (2)
N1—C11—H_c12	59.0 (14)	O2—H_c18—C10	135 (2)
C1—C11—C2	29.1 (2)	O2—H_c18—C14	65.9 (11)
C1—C11—C12	106.9 (4)	O2—H_c18—C18	105 (3)
C1—C11—C15	57.98 (19)	O2—H_c18—H_c10	156 (3)
C1—C11—C19	176.0 (3)	C10—H_c18—C14	69.3 (17)
C1—C11—H_c12	83.4 (14)	C10—H_c18—C18	30.1 (14)
C2—C11—C12	136.0 (5)	C10—H_c18—H_c10	21.3 (12)
C2—C11—C15	28.9 (2)	C14—H_c18—C18	39.2 (16)
C2—C11—C19	154.9 (4)	C14—H_c18—H_c10	91 (2)
C2—C11—H_c12	112.4 (15)	C18—H_c18—H_c10	51 (2)
C12—C11—C15	164.9 (4)	N4—H_c17—C17	39 (2)
C12—C11—C19	69.1 (3)	N4—H_c17—C20	66.7 (15)
C12—C11—H_c12	23.9 (14)	N4—H_c17—H_c9^iv	110 (2)
C15—C11—C19	126.0 (3)	N4—H_c17—H_c3	135 (2)
C15—C11—H_c12	141.2 (14)	C17—H_c17—C20	27.6 (15)
C19—C11—H_c12	92.7 (14)	C17—H_c17—H_c9^iv	146 (4)
O1—C12—N1	72.7 (3)	C17—H_c17—H_c3	96 (3)
O1—C12—C11	37.3 (3)	C20—H_c17—H_c9^iv	160 (2)
O1—C12—C19	36.45 (16)	C20—H_c17—H_c3	68.6 (14)
O1—C12—H_c12	158 (2)	H_c9^iv—H_c17—H_c3	112 (2)
N1—C12—C11	110.0 (4)	O2—H_c22—N4	72.7 (17)
N1—C12—C19	36.2 (2)	O2—H_c22—C22	41.2 (17)
N1—C12—H_c12	127 (3)	N4—H_c22—C22	31.6 (17)

Symmetry codes: (i) −x+1/2, y+1/2, −z−1/2; (ii) −x+1/2, y−1/2, −z−1/2; (iii) x−1/2, −y−1/2, z−1/2; (iv) x+1/2, −y−1/2, z+1/2.

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
C19—H_c19···N2^ii	1.06 (5)	2.37 (5)	3.345 (7)	152 (3)
C18—H_c18···O2	1.05 (5)	2.42 (4)	2.873 (5)	105 (3)

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

(295K)

Crystal data

C24H14N4O2S	F(000) = 872
Mr = 422.5	Dx = 1.510 Mg m^−3
Monoclinic, P21/n	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2yabc	Cell parameters from 2172 reflections
a = 20.7891 (16) Å	θ = 3.9–22.3°
b = 3.8267 (2) Å	µ = 0.21 mm^−1
c = 25.145 (2) Å	T = 295 K
β = 111.747 (7)°	Plate, translucent light yellow
V = 1858.0 (2) Å^3	0.25 × 0.05 × 0.02 mm
Z = 4

Data collection

Xcalibur, EosS2 with high theta cut diffractometer	2198 independent reflections
Radiation source: X-ray tube	1138 reflections with I > 3σ(I)
Graphite monochromator	Rint = 0.062
Detector resolution: 16.1745 pixels mm^-1	θmax = 23.5°, θmin = 3.5°
ω scans	h = −21→21
Absorption correction: analytical CrysAlisPro 1.171.39.46 (Rigaku Oxford Diffraction, 2018) Analytical numeric absorption correction using a multifaceted crystal model based on expressions derived by R.C. Clark & J.S. Reid. (Clark, R. C. & Reid, J. S. (1995). Acta Cryst. A51, 887-897) Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm.	k = −4→3
Tmin = 0.989, Tmax = 0.995	l = −26→26
17975 measured reflections

Refinement

Refinement on F	0 constraints
R[F^2 > 2σ(F^2)] = 0.037	All H-atom parameters refined
wR(F^2) = 0.042	Weighting scheme based on measured s.u.'s w = 1/(σ^2(F) + 0.0001F^2)
S = 1.23	(Δ/σ)max = 0.049
2198 reflections	Δρmax = 0.24 e Å^−3
336 parameters	Δρmin = −0.22 e Å^−3
0 restraints

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

	x	y	z	Uiso*/Ueq
S1	0.42551 (6)	0.3149 (3)	0.03049 (5)	0.0380 (5)
O1	0.15423 (15)	−0.1502 (8)	−0.30236 (13)	0.0370 (14)
O2	0.39459 (17)	0.0440 (9)	0.37549 (16)	0.0533 (17)
N1	0.0547 (2)	0.0262 (9)	−0.36862 (16)	0.0384 (19)
N2	0.35327 (18)	0.2344 (9)	−0.02147 (14)	0.0367 (17)
N3	0.40505 (18)	0.2166 (8)	0.08465 (14)	0.0308 (16)
N4	0.4987 (2)	−0.1462 (11)	0.43301 (17)	0.053 (2)
C1	0.1118 (3)	0.1686 (12)	−0.1801 (2)	0.032 (2)
C2	0.1478 (2)	0.0188 (11)	−0.21153 (19)	0.028 (2)
C3	0.4270 (3)	−0.1794 (11)	0.2449 (2)	0.030 (2)
C4	0.3954 (3)	−0.1568 (12)	0.1856 (2)	0.031 (2)
C5	0.3304 (2)	−0.0084 (11)	0.15977 (19)	0.025 (2)
C6	0.2061 (2)	0.0358 (10)	−0.0921 (2)	0.029 (2)
C7	0.2006 (3)	−0.0433 (11)	0.0052 (2)	0.033 (2)
C8	0.2374 (2)	0.0389 (10)	−0.02832 (19)	0.025 (2)
C9	0.1406 (2)	0.1768 (12)	−0.1209 (2)	0.033 (2)
C10	0.2964 (3)	0.1129 (12)	0.1950 (2)	0.032 (2)
C11	0.1167 (2)	0.0068 (11)	−0.2733 (2)	0.027 (2)
C12	0.0558 (3)	0.1137 (12)	−0.3144 (2)	0.037 (2)
C13	0.2304 (3)	−0.0554 (11)	0.0658 (2)	0.034 (3)
C14	0.3930 (2)	−0.0542 (10)	0.27902 (19)	0.026 (2)
C15	0.2123 (2)	−0.1195 (11)	−0.1823 (2)	0.031 (2)
C16	0.2981 (3)	0.0167 (10)	0.0967 (2)	0.029 (2)
C17	0.4897 (3)	−0.1919 (13)	0.3761 (2)	0.041 (3)
C18	0.3268 (3)	0.0906 (11)	0.2533 (2)	0.029 (2)
C19	0.1129 (3)	−0.1248 (13)	−0.3584 (2)	0.038 (2)
C20	0.4276 (3)	−0.0763 (11)	0.3412 (2)	0.029 (2)
C21	0.2419 (3)	−0.1096 (11)	−0.1237 (2)	0.032 (2)
C22	0.4420 (4)	−0.0126 (18)	0.4289 (3)	0.064 (4)
C23	0.3085 (2)	0.1227 (10)	0.00165 (19)	0.027 (2)
C24	0.3380 (2)	0.1144 (10)	0.06324 (18)	0.027 (2)
H_c10	0.2537 (19)	0.216 (9)	0.1787 (16)	0.023 (12)*
H_c17	0.528 (2)	−0.310 (10)	0.3687 (18)	0.049 (14)*
H_c22	0.4303 (19)	0.054 (9)	0.4540 (17)	0.012 (13)*
H_c18	0.306 (2)	0.176 (10)	0.2828 (19)	0.053 (14)*
H_c3	0.4738 (18)	−0.294 (9)	0.2631 (15)	0.023 (11)*
H_c4	0.422 (2)	−0.261 (11)	0.170 (2)	0.060 (18)*
H_c12	0.020 (2)	0.263 (12)	−0.306 (2)	0.080 (18)*
H_c19	0.1335 (17)	−0.225 (8)	−0.3854 (15)	0.020 (11)*
H_c9	0.1188 (17)	0.295 (8)	−0.0956 (14)	0.015 (10)*
H_c1	0.0669 (18)	0.279 (8)	−0.1997 (15)	0.016 (11)*
H_c13	0.1992 (19)	−0.123 (9)	0.0919 (16)	0.034 (12)*
H_c21	0.2864 (17)	−0.204 (8)	−0.1072 (14)	0.006 (10)*
H_c15	0.2401 (16)	−0.216 (8)	−0.2034 (14)	0.008 (10)*
H_c7	0.146 (2)	−0.111 (9)	−0.0131 (16)	0.038 (12)*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
S1	0.0277 (8)	0.0612 (8)	0.0237 (7)	−0.0127 (7)	0.0080 (6)	−0.0007 (7)
O1	0.0301 (19)	0.057 (2)	0.024 (2)	0.0042 (16)	0.0103 (18)	−0.0003 (17)
O2	0.044 (2)	0.094 (3)	0.017 (2)	0.0175 (19)	0.006 (2)	−0.0013 (19)
N1	0.035 (3)	0.059 (3)	0.019 (3)	0.007 (2)	0.007 (2)	−0.003 (2)
N2	0.036 (3)	0.047 (3)	0.023 (2)	−0.010 (2)	0.006 (2)	0.0006 (19)
N3	0.025 (2)	0.048 (2)	0.020 (2)	−0.0072 (19)	0.0088 (19)	0.0002 (18)
N4	0.047 (3)	0.083 (3)	0.027 (3)	0.012 (3)	0.012 (3)	−0.002 (2)
C1	0.031 (3)	0.036 (3)	0.018 (4)	0.000 (3)	−0.002 (3)	−0.001 (2)
C2	0.032 (4)	0.024 (3)	0.021 (4)	−0.003 (2)	0.002 (3)	−0.002 (2)
C3	0.029 (3)	0.038 (3)	0.024 (3)	0.006 (2)	0.012 (3)	0.005 (2)
C4	0.032 (4)	0.031 (3)	0.031 (4)	−0.003 (3)	0.014 (3)	−0.003 (3)
C5	0.026 (3)	0.029 (3)	0.016 (3)	−0.002 (2)	0.001 (3)	0.001 (2)
C6	0.027 (3)	0.025 (3)	0.030 (4)	−0.009 (2)	0.006 (3)	−0.002 (2)
C7	0.024 (3)	0.048 (3)	0.031 (4)	−0.007 (2)	0.015 (3)	0.001 (2)
C8	0.020 (3)	0.034 (3)	0.023 (3)	−0.001 (2)	0.011 (3)	0.002 (2)
C9	0.026 (3)	0.035 (3)	0.036 (4)	0.002 (2)	0.010 (3)	−0.004 (3)
C10	0.029 (3)	0.036 (3)	0.030 (4)	0.005 (2)	0.012 (3)	0.001 (2)
C11	0.025 (3)	0.034 (3)	0.025 (4)	−0.002 (2)	0.015 (3)	−0.001 (2)
C12	0.035 (4)	0.047 (3)	0.027 (3)	0.008 (3)	0.007 (3)	−0.005 (3)
C13	0.034 (4)	0.040 (3)	0.030 (4)	−0.006 (2)	0.013 (3)	−0.002 (2)
C14	0.029 (3)	0.031 (3)	0.020 (3)	−0.005 (2)	0.013 (3)	0.001 (2)
C15	0.021 (3)	0.034 (3)	0.040 (4)	0.001 (2)	0.013 (3)	0.002 (3)
C16	0.031 (4)	0.028 (3)	0.025 (3)	−0.003 (2)	0.006 (3)	0.001 (2)
C17	0.043 (4)	0.058 (3)	0.025 (4)	0.006 (3)	0.016 (3)	−0.003 (3)
C18	0.035 (4)	0.036 (3)	0.020 (4)	−0.002 (2)	0.016 (3)	−0.001 (2)
C19	0.040 (4)	0.058 (3)	0.020 (4)	0.003 (3)	0.014 (3)	−0.004 (3)
C20	0.036 (4)	0.038 (3)	0.020 (4)	0.002 (2)	0.018 (3)	−0.004 (2)
C21	0.026 (4)	0.038 (3)	0.026 (4)	0.006 (2)	0.003 (3)	0.004 (2)
C22	0.064 (5)	0.111 (5)	0.023 (5)	0.005 (4)	0.022 (5)	−0.009 (4)
C23	0.025 (3)	0.030 (3)	0.025 (3)	−0.007 (2)	0.007 (3)	0.004 (2)
C24	0.026 (3)	0.035 (3)	0.016 (3)	0.002 (2)	0.003 (3)	0.000 (2)

Geometric parameters (Å, º)

S1—N2	1.614 (3)	C5—H_c4	2.06 (5)
S1—N3	1.614 (4)	C6—C8	1.491 (6)
S1—C23	2.382 (5)	C6—C9	1.393 (6)
S1—C24	2.385 (6)	C6—C15	2.393 (8)
O1—N1	2.227 (4)	C6—C21	1.389 (8)
O1—C2	2.425 (6)	C6—H_c9	2.04 (4)
O1—C11	1.388 (7)	C6—H_c21	2.06 (4)
O1—C12	2.201 (6)	C7—C8	1.369 (8)
O1—C19	1.355 (5)	C7—C13	1.417 (7)
O1—H_c19	1.99 (4)	C7—C16	2.449 (6)
O1—H_c15	2.48 (3)	C7—C23	2.366 (8)
O2—N4	2.233 (5)	C7—H_c13	2.21 (4)
O2—C14	2.443 (6)	C7—H_c7	1.09 (4)
O2—C17	2.168 (7)	C8—C13	2.451 (8)
O2—C20	1.367 (7)	C8—C21	2.500 (8)
O2—C22	1.358 (7)	C8—C23	1.426 (6)
O2—H_c22	1.83 (4)	C8—C24	2.488 (5)
O2—H_c18	2.43 (4)	C8—H_c7	2.15 (5)
N1—C11	2.264 (6)	C9—C21	2.398 (8)
N1—C12	1.397 (7)	C9—H_c9	1.01 (4)
N1—C19	1.279 (7)	C9—H_c1	2.04 (3)
N1—H_c12	2.15 (6)	C10—C14	2.400 (6)
N1—H_c19	2.07 (4)	C10—C18	1.366 (7)
N2—N3	2.481 (5)	C10—H_c10	0.92 (4)
N2—C8	2.467 (6)	C10—H_c18	2.15 (5)
N2—C23	1.336 (7)	C11—C12	1.367 (6)
N2—C24	2.313 (6)	C11—C15	2.459 (6)
N2—H_c19^i	2.46 (4)	C11—C19	2.172 (8)
N3—C16	2.473 (7)	C11—H_c12	2.11 (5)
N3—C23	2.325 (5)	C12—C19	2.109 (9)
N3—C24	1.353 (6)	C12—H_c12	1.01 (5)
N4—C17	1.383 (7)	C13—C16	1.360 (7)
N4—C20	2.250 (6)	C13—C24	2.353 (8)
N4—C22	1.254 (9)	C13—H_c13	1.11 (5)
N4—H_c17	2.03 (5)	C13—H_c7	2.12 (3)
N4—H_c22	1.85 (5)	C14—C18	1.399 (6)
C1—C2	1.396 (8)	C14—C20	1.460 (6)
C1—C6	2.405 (6)	C14—H_c18	2.04 (5)
C1—C9	1.383 (7)	C14—H_c3	2.08 (4)
C1—C11	2.461 (8)	C15—C21	1.371 (7)
C1—C15	2.381 (8)	C15—H_c21	1.97 (3)
C1—H_c9	2.13 (4)	C15—H_c15	0.99 (4)
C1—H_c1	0.98 (3)	C16—C24	1.432 (8)
C2—C9	2.415 (8)	C16—H_c13	2.08 (4)
C2—C11	1.445 (6)	C17—C20	1.339 (7)
C2—C15	1.375 (6)	C17—C22	2.048 (11)
C2—C21	2.397 (6)	C17—H_c17	0.99 (5)
C2—H_c1	2.07 (4)	C18—C20	2.499 (6)
C2—H_c15	2.06 (3)	C18—H_c10	1.99 (3)
C3—C4	1.392 (7)	C18—H_c18	1.04 (5)
C3—C5	2.421 (6)	C19—H_c19	1.00 (4)
C3—C14	1.382 (8)	C20—C22	2.129 (9)
C3—C18	2.402 (8)	C20—H_c17	2.14 (4)
C3—C20	2.447 (8)	C21—H_c21	0.94 (3)
C3—H_c3	1.01 (3)	C21—H_c15	2.03 (4)
C3—H_c4	1.86 (5)	C22—H_c22	0.80 (5)
C4—C5	1.386 (6)	C23—C24	1.439 (6)
C4—C10	2.391 (8)	H_c10—H_c18	2.44 (6)
C4—C14	2.399 (8)	H_c10—H_c13	2.43 (5)
C4—C16	2.486 (6)	H_c17—H_c3	2.47 (5)
C4—H_c3	2.09 (3)	H_c3—H_c4	2.18 (6)
C4—H_c4	0.88 (6)	H_c12—H_c1	2.49 (6)
C5—C10	1.402 (8)	H_c9—H_c1	2.43 (5)
C5—C16	1.479 (6)	H_c9—H_c7	2.48 (5)
C5—C18	2.410 (8)	H_c13—H_c7	2.45 (5)
C5—H_c10	2.02 (4)	H_c21—H_c15	2.25 (5)
N2—S1—N3	100.5 (2)	N1—C12—C11	109.9 (5)
N2—S1—C23	32.39 (19)	N1—C12—C19	36.1 (2)
N2—S1—C24	67.54 (18)	N1—C12—H_c12	126 (3)
N3—S1—C23	68.07 (16)	C11—C12—C19	73.9 (4)
N3—S1—C24	32.92 (14)	C11—C12—H_c12	124 (3)
C23—S1—C24	35.15 (15)	C19—C12—H_c12	161 (3)
N1—O1—C2	105.3 (2)	C7—C13—C8	27.9 (3)
N1—O1—C11	73.5 (2)	C7—C13—C16	123.7 (6)
N1—O1—C12	36.78 (18)	C7—C13—C24	90.2 (4)
N1—O1—C19	31.2 (3)	C7—C13—H_c13	121.6 (17)
N1—O1—H_c19	58.6 (10)	C7—C13—H_c7	27.8 (13)
N1—O1—H_c15	154.9 (9)	C8—C13—C16	95.9 (4)
C2—O1—C11	31.8 (2)	C8—C13—C24	62.4 (2)
C2—O1—C12	68.51 (19)	C8—C13—H_c13	149.4 (17)
C2—O1—C19	136.5 (3)	C8—C13—H_c7	55.6 (13)
C2—O1—H_c19	163.9 (10)	C16—C13—C24	33.5 (3)
C2—O1—H_c15	49.7 (9)	C16—C13—H_c13	114.7 (17)
C11—O1—C12	36.7 (2)	C16—C13—H_c7	151.5 (14)
C11—O1—C19	104.7 (4)	C24—C13—H_c13	148.2 (17)
C11—O1—H_c19	132.0 (10)	C24—C13—H_c7	118.0 (13)
C11—O1—H_c15	81.5 (9)	H_c13—C13—H_c7	94 (2)
C12—O1—C19	68.0 (3)	O2—C14—C3	147.9 (3)
C12—O1—H_c19	95.4 (10)	O2—C14—C4	178.1 (3)
C12—O1—H_c15	118.2 (9)	O2—C14—C10	122.1 (3)
C19—O1—H_c19	27.3 (10)	O2—C14—C18	92.7 (4)
C19—O1—H_c15	173.7 (10)	O2—C14—C20	29.1 (3)
H_c19—O1—H_c15	146.4 (13)	O2—C14—H_c18	64.8 (12)
N4—O2—C14	104.2 (2)	O2—C14—H_c3	123.0 (9)
N4—O2—C17	36.59 (19)	C3—C14—C4	30.3 (2)
N4—O2—C20	72.9 (3)	C3—C14—C10	90.0 (3)
N4—O2—C22	29.9 (4)	C3—C14—C18	119.4 (4)
N4—O2—H_c22	53.2 (13)	C3—C14—C20	118.7 (4)
N4—O2—H_c18	153.8 (12)	C3—C14—H_c18	147.3 (13)
C14—O2—C17	67.7 (2)	C3—C14—H_c3	24.9 (9)
C14—O2—C20	31.3 (2)	C4—C14—C10	59.8 (2)
C14—O2—C22	134.1 (4)	C4—C14—C18	89.2 (3)
C14—O2—H_c22	157.4 (13)	C4—C14—C20	149.0 (4)
C14—O2—H_c18	49.6 (12)	C4—C14—H_c18	117.1 (12)
C17—O2—C20	36.3 (2)	C4—C14—H_c3	55.2 (9)
C17—O2—C22	66.5 (4)	C10—C14—C18	29.4 (3)
C17—O2—H_c22	89.8 (13)	C10—C14—C20	151.2 (4)
C17—O2—H_c18	117.2 (12)	C10—C14—H_c18	57.3 (12)
C20—O2—C22	102.8 (5)	C10—C14—H_c3	114.9 (9)
C20—O2—H_c22	126.1 (13)	C18—C14—C20	121.8 (5)
C20—O2—H_c18	80.9 (12)	C18—C14—H_c18	27.9 (12)
C22—O2—H_c22	23.3 (13)	C18—C14—H_c3	144.3 (10)
C22—O2—H_c18	176.0 (12)	C20—C14—H_c18	93.9 (13)
H_c22—O2—H_c18	152.9 (17)	C20—C14—H_c3	93.9 (10)
O1—N1—C11	36.00 (17)	H_c18—C14—H_c3	172.1 (15)
O1—N1—C12	70.6 (3)	C1—C15—C2	31.0 (3)
O1—N1—C19	33.3 (3)	C1—C15—C6	60.5 (2)
O1—N1—H_c12	92.8 (11)	C1—C15—C11	61.1 (2)
O1—N1—H_c19	55.0 (9)	C1—C15—C21	90.6 (4)
C11—N1—C12	34.6 (3)	C1—C15—H_c21	115.8 (12)
C11—N1—C19	69.3 (3)	C1—C15—H_c15	151.3 (17)
C11—N1—H_c12	56.9 (11)	C2—C15—C6	91.5 (4)
C11—N1—H_c19	91.0 (9)	C2—C15—C11	30.1 (3)
C12—N1—C19	103.9 (4)	C2—C15—C21	121.6 (5)
C12—N1—H_c12	22.4 (11)	C2—C15—H_c21	146.8 (12)
C12—N1—H_c19	125.6 (10)	C2—C15—H_c15	120.3 (17)
C19—N1—H_c12	126.1 (12)	C6—C15—C11	121.6 (3)
C19—N1—H_c19	21.7 (10)	C6—C15—C21	30.1 (3)
H_c12—N1—H_c19	147.7 (14)	C6—C15—H_c21	55.3 (12)
S1—N2—N3	39.78 (13)	C6—C15—H_c15	148.0 (16)
S1—N2—C8	134.9 (2)	C11—C15—C21	151.7 (4)
S1—N2—C23	107.3 (3)	C11—C15—H_c21	176.8 (11)
S1—N2—C24	72.32 (17)	C11—C15—H_c15	90.3 (16)
S1—N2—H_c19^i	111.1 (8)	C21—C15—H_c21	25.2 (12)
N3—N2—C8	95.2 (2)	C21—C15—H_c15	117.9 (17)
N3—N2—C23	67.5 (2)	H_c21—C15—H_c15	93 (2)
N3—N2—C24	32.54 (14)	N3—C16—C4	74.0 (2)
N3—N2—H_c19^i	150.2 (8)	N3—C16—C5	94.6 (3)
C8—N2—C23	27.7 (2)	N3—C16—C7	112.5 (3)
C8—N2—C24	62.64 (18)	N3—C16—C13	141.3 (4)
C8—N2—H_c19^i	113.8 (8)	N3—C16—C24	26.52 (19)
C23—N2—C24	35.0 (2)	N3—C16—H_c13	169.9 (11)
C23—N2—H_c19^i	140.8 (8)	C4—C16—C5	28.7 (3)
C24—N2—H_c19^i	172.0 (7)	C4—C16—C7	159.1 (2)
S1—N3—N2	39.76 (12)	C4—C16—C13	141.6 (4)
S1—N3—C16	134.82 (19)	C4—C16—C24	98.2 (3)
S1—N3—C23	71.84 (18)	C4—C16—H_c13	116.1 (10)
S1—N3—C24	106.7 (3)	C5—C16—C7	152.9 (4)
N2—N3—C16	95.08 (17)	C5—C16—C13	124.1 (5)
N2—N3—C23	32.08 (17)	C5—C16—C24	121.0 (4)
N2—N3—C24	66.9 (3)	C5—C16—H_c13	95.2 (11)
C16—N3—C23	63.01 (19)	C7—C16—C13	28.8 (3)
C16—N3—C24	28.2 (3)	C7—C16—C24	86.1 (3)
C23—N3—C24	34.8 (3)	C7—C16—H_c13	57.7 (11)
O2—N4—C17	69.1 (3)	C13—C16—C24	114.8 (4)
O2—N4—C20	35.50 (19)	C13—C16—H_c13	29.0 (11)
O2—N4—C22	32.6 (3)	C24—C16—H_c13	143.8 (11)
O2—N4—H_c17	95.2 (10)	O2—C17—N4	74.3 (4)
O2—N4—H_c22	52.3 (11)	O2—C17—C20	37.2 (3)
C17—N4—C20	33.6 (3)	O2—C17—C22	37.4 (2)
C17—N4—C22	101.8 (5)	O2—C17—H_c17	169 (2)
C17—N4—H_c17	26.1 (11)	N4—C17—C20	111.4 (5)
C17—N4—H_c22	121.4 (12)	N4—C17—C22	36.8 (3)
C20—N4—C22	68.1 (4)	N4—C17—H_c17	116 (2)
C20—N4—H_c17	59.7 (10)	C20—C17—C22	74.6 (4)
C20—N4—H_c22	87.8 (12)	C20—C17—H_c17	132 (2)
C22—N4—H_c17	127.8 (11)	C22—C17—H_c17	153 (2)
C22—N4—H_c22	19.7 (12)	C3—C18—C5	60.4 (2)
H_c17—N4—H_c22	147.5 (15)	C3—C18—C10	90.3 (4)
C2—C1—C6	90.5 (3)	C3—C18—C14	30.1 (3)
C2—C1—C9	120.7 (4)	C3—C18—C20	59.8 (2)
C2—C1—C11	30.5 (2)	C3—C18—H_c10	114.0 (13)
C2—C1—C15	30.5 (2)	C3—C18—H_c18	143 (2)
C2—C1—H_c9	143.5 (9)	C5—C18—C10	29.9 (3)
C2—C1—H_c1	120 (2)	C5—C18—C14	90.5 (4)
C6—C1—C9	30.1 (3)	C5—C18—C20	120.2 (3)
C6—C1—C11	121.0 (3)	C5—C18—H_c10	53.6 (13)
C6—C1—C15	60.0 (2)	C5—C18—H_c18	157 (2)
C6—C1—H_c9	53.1 (9)	C10—C18—C14	120.4 (5)
C6—C1—H_c1	149 (2)	C10—C18—C20	150.1 (5)
C9—C1—C11	151.2 (4)	C10—C18—H_c10	23.7 (13)
C9—C1—C15	90.1 (3)	C10—C18—H_c18	127 (2)
C9—C1—H_c9	23.0 (9)	C14—C18—C20	29.8 (3)
C9—C1—H_c1	119 (2)	C14—C18—H_c10	144.0 (14)
C11—C1—C15	61.0 (2)	C14—C18—H_c18	113 (2)
C11—C1—H_c9	174.0 (9)	C20—C18—H_c10	173.6 (14)
C11—C1—H_c1	90 (2)	C20—C18—H_c18	83 (2)
C15—C1—H_c9	113.1 (9)	H_c10—C18—H_c18	103 (2)
C15—C1—H_c1	151 (2)	O1—C19—N1	115.4 (5)
H_c9—C1—H_c1	96 (3)	O1—C19—C11	38.2 (2)
O1—C2—C1	150.5 (3)	O1—C19—C12	75.4 (3)
O1—C2—C9	179.0 (2)	O1—C19—H_c19	114.3 (18)
O1—C2—C11	30.4 (2)	N1—C19—C11	77.2 (4)
O1—C2—C15	91.0 (4)	N1—C19—C12	40.0 (3)
O1—C2—C21	120.1 (3)	N1—C19—H_c19	130.2 (18)
O1—C2—H_c1	126.5 (9)	C11—C19—C12	37.2 (2)
O1—C2—H_c15	66.5 (9)	C11—C19—H_c19	152.5 (17)
C1—C2—C9	29.5 (2)	C12—C19—H_c19	170.2 (17)
C1—C2—C11	120.1 (4)	O2—C20—N4	71.6 (3)
C1—C2—C15	118.5 (4)	O2—C20—C3	149.2 (3)
C1—C2—C21	89.3 (3)	O2—C20—C14	119.5 (4)
C1—C2—H_c1	24.1 (9)	O2—C20—C17	106.5 (4)
C1—C2—H_c15	142.9 (10)	O2—C20—C18	91.1 (3)
C9—C2—C11	149.6 (4)	O2—C20—C22	38.5 (3)
C9—C2—C15	88.9 (3)	O2—C20—H_c17	126.6 (13)
C9—C2—C21	59.8 (2)	N4—C20—C3	139.2 (3)
C9—C2—H_c1	53.6 (9)	N4—C20—C14	168.8 (5)
C9—C2—H_c15	113.4 (9)	N4—C20—C17	34.9 (3)
C11—C2—C15	121.4 (5)	N4—C20—C18	162.6 (3)
C11—C2—C21	150.6 (4)	N4—C20—C22	33.1 (3)
C11—C2—H_c1	96.1 (10)	N4—C20—H_c17	55.0 (12)
C11—C2—H_c15	97.0 (10)	C3—C20—C14	29.7 (3)
C15—C2—C21	29.2 (3)	C3—C20—C17	104.3 (4)
C15—C2—H_c1	142.5 (10)	C3—C20—C18	58.1 (2)
C15—C2—H_c15	24.5 (10)	C3—C20—C22	172.3 (3)
C21—C2—H_c1	113.3 (9)	C3—C20—H_c17	84.2 (12)
C21—C2—H_c15	53.6 (9)	C14—C20—C17	134.0 (6)
H_c1—C2—H_c15	166.7 (13)	C14—C20—C18	28.4 (3)
C4—C3—C5	29.3 (3)	C14—C20—C22	158.0 (5)
C4—C3—C14	119.7 (4)	C14—C20—H_c17	113.9 (13)
C4—C3—C18	89.2 (3)	C17—C20—C18	162.4 (5)
C4—C3—C20	151.3 (4)	C17—C20—C22	68.0 (4)
C4—C3—H_c3	120 (2)	C17—C20—H_c17	20.1 (12)
C4—C3—H_c4	26.5 (14)	C18—C20—C22	129.6 (4)
C5—C3—C14	90.4 (3)	C18—C20—H_c17	142.3 (13)
C5—C3—C18	60.0 (2)	C22—C20—H_c17	88.1 (13)
C5—C3—C20	122.0 (3)	C2—C21—C6	91.0 (3)
C5—C3—H_c3	150 (2)	C2—C21—C8	122.0 (3)
C5—C3—H_c4	55.8 (14)	C2—C21—C9	60.5 (2)
C14—C3—C18	30.5 (2)	C2—C21—C15	29.2 (3)
C14—C3—C20	31.6 (2)	C2—C21—H_c21	145 (2)
C14—C3—H_c3	120 (2)	C2—C21—H_c15	54.7 (9)
C14—C3—H_c4	146.1 (14)	C6—C21—C8	31.0 (2)
C18—C3—C20	62.1 (2)	C6—C21—C9	30.5 (2)
C18—C3—H_c3	150 (2)	C6—C21—C15	120.2 (4)
C18—C3—H_c4	115.7 (14)	C6—C21—H_c21	124 (2)
C20—C3—H_c3	88 (2)	C6—C21—H_c15	145.7 (9)
C20—C3—H_c4	177.3 (15)	C8—C21—C9	61.5 (2)
H_c3—C3—H_c4	94 (3)	C8—C21—C15	151.2 (4)
C3—C4—C5	121.3 (5)	C8—C21—H_c21	93 (2)
C3—C4—C10	90.2 (4)	C8—C21—H_c15	176.6 (9)
C3—C4—C14	30.0 (3)	C9—C21—C15	89.7 (3)
C3—C4—C16	152.2 (5)	C9—C21—H_c21	154 (2)
C3—C4—H_c3	24.6 (12)	C9—C21—H_c15	115.2 (9)
C3—C4—H_c4	108 (3)	C15—C21—H_c21	116 (2)
C5—C4—C10	31.2 (3)	C15—C21—H_c15	25.5 (9)
C5—C4—C14	91.3 (4)	H_c21—C21—H_c15	91 (2)
C5—C4—C16	30.9 (3)	O2—C22—N4	117.5 (7)
C5—C4—H_c3	145.9 (13)	O2—C22—C17	76.1 (4)
C5—C4—H_c4	130 (3)	O2—C22—C20	38.8 (3)
C10—C4—C14	60.1 (2)	O2—C22—H_c22	114 (2)
C10—C4—C16	62.0 (2)	N4—C22—C17	41.4 (3)
C10—C4—H_c3	114.8 (12)	N4—C22—C20	78.7 (5)
C10—C4—H_c4	161 (3)	N4—C22—H_c22	128 (2)
C14—C4—C16	122.2 (3)	C17—C22—C20	37.3 (2)
C14—C4—H_c3	54.6 (12)	C17—C22—H_c22	170 (2)
C14—C4—H_c4	138 (3)	C20—C22—H_c22	153 (2)
C16—C4—H_c3	176.8 (12)	S1—C23—N2	40.30 (18)
C16—C4—H_c4	99 (3)	S1—C23—N3	40.09 (13)
H_c3—C4—H_c4	84 (3)	S1—C23—C7	161.3 (3)
C3—C5—C4	29.4 (3)	S1—C23—C8	166.6 (4)
C3—C5—C10	88.7 (3)	S1—C23—C24	72.5 (3)
C3—C5—C16	149.8 (4)	N2—C23—N3	80.4 (2)
C3—C5—C18	59.6 (2)	N2—C23—C7	157.7 (3)
C3—C5—H_c10	112.1 (10)	N2—C23—C8	126.5 (4)
C3—C5—H_c4	48.3 (14)	N2—C23—C24	112.8 (4)
C4—C5—C10	118.1 (4)	N3—C23—C7	121.5 (3)
C4—C5—C16	120.4 (5)	N3—C23—C8	152.9 (4)
C4—C5—C18	89.0 (3)	N3—C23—C24	32.4 (2)
C4—C5—H_c10	141.5 (10)	C7—C23—C8	31.4 (3)
C4—C5—H_c4	18.9 (14)	C7—C23—C24	89.1 (3)
C10—C5—C16	121.5 (4)	C8—C23—C24	120.5 (5)
C10—C5—C18	29.1 (2)	S1—C24—N2	40.14 (12)
C10—C5—H_c10	23.4 (10)	S1—C24—N3	40.4 (2)
C10—C5—H_c4	136.9 (14)	S1—C24—C8	101.8 (2)
C16—C5—C18	150.6 (4)	S1—C24—C13	162.3 (2)
C16—C5—H_c10	98.1 (10)	S1—C24—C16	165.6 (3)
C16—C5—H_c4	101.5 (14)	S1—C24—C23	72.3 (3)
C18—C5—H_c10	52.4 (10)	N2—C24—N3	80.6 (3)
C18—C5—H_c4	107.9 (14)	N2—C24—C8	61.71 (18)
H_c10—C5—H_c4	160.3 (17)	N2—C24—C13	122.4 (2)
C1—C6—C8	150.5 (4)	N2—C24—C16	154.1 (3)
C1—C6—C9	29.9 (3)	N2—C24—C23	32.2 (2)
C1—C6—C15	59.5 (2)	N3—C24—C8	142.3 (4)
C1—C6—C21	89.2 (3)	N3—C24—C13	156.8 (4)
C1—C6—H_c9	56.5 (10)	N3—C24—C16	125.3 (4)
C1—C6—H_c21	111.4 (9)	N3—C24—C23	112.7 (4)
C8—C6—C9	120.6 (5)	C8—C24—C13	60.8 (2)
C8—C6—C15	150.0 (4)	C8—C24—C16	92.4 (3)
C8—C6—C21	120.4 (4)	C8—C24—C23	29.6 (3)
C8—C6—H_c9	94.0 (10)	C13—C24—C16	31.6 (2)
C8—C6—H_c21	98.2 (9)	C13—C24—C23	90.3 (3)
C9—C6—C15	89.4 (3)	C16—C24—C23	122.0 (4)
C9—C6—C21	119.0 (4)	C5—H_c10—C10	37 (2)
C9—C6—H_c9	26.7 (10)	C5—H_c10—C18	74.0 (12)
C9—C6—H_c21	141.3 (9)	C5—H_c10—H_c18	98.5 (17)
C15—C6—C21	29.7 (2)	C5—H_c10—H_c13	73.0 (16)
C15—C6—H_c9	116.0 (10)	C10—H_c10—C18	36.7 (16)
C15—C6—H_c21	51.9 (9)	C10—H_c10—H_c18	61 (2)
C21—C6—H_c9	145.6 (10)	C10—H_c10—H_c13	103 (3)
C21—C6—H_c21	22.2 (9)	C18—H_c10—H_c18	24.5 (12)
H_c9—C6—H_c21	167.6 (13)	C18—H_c10—H_c13	131.2 (18)
C8—C7—C13	123.2 (4)	H_c18—H_c10—H_c13	144 (2)
C8—C7—C16	95.7 (3)	N4—H_c17—C17	37.7 (18)
C8—C7—C23	32.9 (2)	N4—H_c17—C20	65.3 (15)
C8—C7—H_c13	148.5 (10)	N4—H_c17—H_c3	134 (2)
C8—C7—H_c7	122 (2)	C17—H_c17—C20	27.6 (13)
C13—C7—C16	27.5 (3)	C17—H_c17—H_c3	96 (2)
C13—C7—C23	90.3 (3)	C20—H_c17—H_c3	68.9 (14)
C13—C7—H_c13	25.3 (10)	O2—H_c22—N4	74.5 (18)
C13—C7—H_c7	115 (2)	O2—H_c22—C22	42.5 (19)
C16—C7—C23	62.8 (2)	N4—H_c22—C22	32.0 (18)
C16—C7—H_c13	52.8 (9)	O2—H_c18—C10	135 (2)
C16—C7—H_c7	142 (2)	O2—H_c18—C14	65.6 (10)
C23—C7—H_c13	115.7 (9)	O2—H_c18—C18	105 (2)
C23—C7—H_c7	155 (2)	O2—H_c18—H_c10	157 (2)
H_c13—C7—H_c7	89 (2)	C10—H_c18—C14	69.7 (16)
N2—C8—C6	95.9 (3)	C10—H_c18—C18	30.6 (14)
N2—C8—C7	141.4 (3)	C10—H_c18—H_c10	21.9 (11)
N2—C8—C13	112.5 (2)	C14—H_c18—C18	39.1 (15)
N2—C8—C21	75.7 (2)	C14—H_c18—H_c10	92 (2)
N2—C8—C23	25.8 (2)	C18—H_c18—H_c10	53 (2)
N2—C8—C24	55.65 (17)	C3—H_c3—C4	35.0 (14)
N2—C8—H_c7	166.6 (10)	C3—H_c3—C14	35.2 (17)
C6—C8—C7	122.7 (4)	C3—H_c3—H_c17	118 (3)
C6—C8—C13	151.6 (4)	C3—H_c3—H_c4	59 (2)
C6—C8—C21	28.7 (3)	C4—H_c3—C14	70.2 (11)
C6—C8—C23	121.6 (5)	C4—H_c3—H_c17	153 (2)
C6—C8—C24	151.4 (4)	C4—H_c3—H_c4	23.6 (14)
C6—C8—H_c7	97.4 (10)	C14—H_c3—H_c17	83.4 (18)
C7—C8—C13	28.9 (2)	C14—H_c3—H_c4	93.8 (19)
C7—C8—C21	140.1 (3)	H_c17—H_c3—H_c4	177 (3)
C7—C8—C23	115.7 (4)	C3—H_c4—C4	45 (2)
C7—C8—C24	85.8 (3)	C3—H_c4—C5	76 (2)
C7—C8—H_c7	25.4 (9)	C3—H_c4—H_c3	27.6 (12)
C13—C8—C21	158.4 (2)	C4—H_c4—C5	30.8 (18)
C13—C8—C23	86.8 (3)	C4—H_c4—H_c3	73 (3)
C13—C8—C24	56.9 (2)	C5—H_c4—H_c3	103 (3)
C13—C8—H_c7	54.3 (9)	N1—H_c12—C11	64.2 (16)
C21—C8—C23	99.1 (4)	N1—H_c12—C12	31.7 (19)
C21—C8—C24	126.6 (3)	N1—H_c12—H_c1	134 (2)
C21—C8—H_c7	117.4 (10)	C11—H_c12—C12	32.7 (15)
C23—C8—C24	29.9 (3)	C11—H_c12—H_c1	69.8 (15)
C23—C8—H_c7	141.1 (10)	C12—H_c12—H_c1	102 (3)
C24—C8—H_c7	111.2 (10)	O1—H_c19—N1	66.4 (13)
C1—C9—C2	29.8 (3)	O1—H_c19—N2^ii	161.8 (18)
C1—C9—C6	120.0 (5)	O1—H_c19—C19	38.3 (13)
C1—C9—C21	89.6 (4)	N1—H_c19—N2^ii	126.7 (14)
C1—C9—H_c9	124.8 (17)	N1—H_c19—C19	28.1 (11)
C1—C9—H_c1	24.7 (12)	N2^ii—H_c19—C19	153 (2)
C2—C9—C6	90.2 (4)	C1—H_c9—C6	70.4 (13)
C2—C9—C21	59.7 (2)	C1—H_c9—C9	32.2 (12)
C2—C9—H_c9	154.4 (17)	C1—H_c9—H_c1	23.5 (10)
C2—C9—H_c1	54.5 (12)	C1—H_c9—H_c7	127.1 (17)
C6—C9—C21	30.4 (3)	C6—H_c9—C9	38.2 (12)
C6—C9—H_c9	115.1 (17)	C6—H_c9—H_c1	93.9 (18)
C6—C9—H_c1	144.6 (13)	C6—H_c9—H_c7	74.8 (14)
C21—C9—H_c9	145.4 (16)	C9—H_c9—H_c1	55.7 (18)
C21—C9—H_c1	114.2 (12)	C9—H_c9—H_c7	103 (2)
H_c9—C9—H_c1	100 (2)	H_c1—H_c9—H_c7	139.1 (17)
C4—C10—C5	30.7 (2)	C1—H_c1—C2	35.7 (17)
C4—C10—C14	60.1 (2)	C1—H_c1—C9	36.3 (14)
C4—C10—C18	90.3 (4)	C1—H_c1—H_c12	117 (3)
C4—C10—H_c10	150 (3)	C1—H_c1—H_c9	60 (2)
C4—C10—H_c18	113.1 (11)	C2—H_c1—C9	71.9 (11)
C5—C10—C14	90.8 (3)	C2—H_c1—H_c12	81.2 (18)
C5—C10—C18	121.0 (5)	C2—H_c1—H_c9	96.1 (14)
C5—C10—H_c10	119 (3)	C9—H_c1—H_c12	153 (2)
C5—C10—H_c18	143.8 (11)	C9—H_c1—H_c9	24.2 (10)
C14—C10—C18	30.2 (3)	H_c12—H_c1—H_c9	177 (2)
C14—C10—H_c10	150 (3)	C7—H_c13—C13	33.1 (12)
C14—C10—H_c18	53.0 (11)	C7—H_c13—C16	69.4 (14)
C18—C10—H_c10	120 (3)	C7—H_c13—H_c10	129.8 (19)
C18—C10—H_c18	22.8 (11)	C7—H_c13—H_c7	26.3 (12)
H_c10—C10—H_c18	97 (3)	C13—H_c13—C16	36.3 (12)
O1—C11—N1	70.5 (2)	C13—H_c13—H_c10	103 (2)
O1—C11—C1	147.1 (3)	C13—H_c13—H_c7	59 (2)
O1—C11—C2	117.7 (4)	C16—H_c13—H_c10	71.9 (14)
O1—C11—C12	106.0 (4)	C16—H_c13—H_c7	96 (2)
O1—C11—C15	89.2 (3)	H_c10—H_c13—H_c7	146.2 (19)
O1—C11—C19	37.1 (2)	C6—H_c21—C15	72.8 (11)
O1—C11—H_c12	129.4 (15)	C6—H_c21—C21	34.2 (17)
N1—C11—C1	142.3 (3)	C6—H_c21—H_c15	98.9 (15)
N1—C11—C2	171.7 (4)	C15—H_c21—C21	38.6 (14)
N1—C11—C12	35.5 (3)	C15—H_c21—H_c15	26.1 (10)
N1—C11—C15	159.8 (3)	C21—H_c21—H_c15	65 (2)
N1—C11—C19	33.43 (19)	O1—H_c15—C2	63.8 (8)
N1—C11—H_c12	58.9 (15)	O1—H_c15—C15	98.8 (19)
C1—C11—C2	29.4 (3)	O1—H_c15—C21	135.4 (17)
C1—C11—C12	106.9 (4)	O1—H_c15—H_c21	160 (2)
C1—C11—C15	57.9 (2)	C2—H_c15—C15	35.1 (11)
C1—C11—C19	175.7 (3)	C2—H_c15—C21	71.7 (13)
C1—C11—H_c12	83.5 (15)	C2—H_c15—H_c21	96.3 (18)
C2—C11—C12	136.3 (5)	C15—H_c15—C21	36.6 (13)
C2—C11—C15	28.5 (3)	C15—H_c15—H_c21	61.1 (19)
C2—C11—C19	154.8 (4)	C21—H_c15—H_c21	24.6 (10)
C2—C11—H_c12	112.8 (15)	C7—H_c7—C8	32.7 (16)
C12—C11—C15	164.8 (5)	C7—H_c7—C13	37.4 (13)
C12—C11—C19	68.9 (3)	C7—H_c7—H_c9	95 (3)
C12—C11—H_c12	23.6 (15)	C7—H_c7—H_c13	64 (2)
C15—C11—C19	126.4 (3)	C8—H_c7—C13	70.1 (12)
C15—C11—H_c12	141.2 (15)	C8—H_c7—H_c9	68.1 (15)
C19—C11—H_c12	92.3 (15)	C8—H_c7—H_c13	96.9 (16)
O1—C12—N1	72.6 (3)	C13—H_c7—H_c9	125.0 (18)
O1—C12—C11	37.3 (3)	C13—H_c7—H_c13	26.8 (11)
O1—C12—C19	36.57 (18)	H_c9—H_c7—H_c13	141.5 (18)
O1—C12—H_c12	160 (2)

Symmetry codes: (i) −x+1/2, y+1/2, −z−1/2; (ii) −x+1/2, y−1/2, −z−1/2.

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
C18—H_c18···O2	1.04 (5)	2.43 (4)	2.872 (6)	105 (2)
C19—H_c19···N2^ii	1.00 (4)	2.46 (4)	3.388 (7)	153 (2)
C15—H_c15···O1	0.99 (4)	2.48 (3)	2.808 (6)	98.8 (19)

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