Tetra-butyl-ammonium N-benzoyl-6-nitro-1,3-benzothia-zol-2-aminide.

In the title salt, C(16)H(36)N(+)·C(14)H(8)N(3)O(3)S(-), the torsion angles within the cation reveal that one butyl group displays an anti conformation and the other three butyl groups show gauche conformations. The anion is almost planar, with a largest deviation of 0.166 (6) Å from the least-squares plane (r.m.s. deviation of fitted atoms = 0.052 Å). In the crystal structure, the component ions inter-act by means of weak inter-molecular C-H⋯O hydrogen bonds.

Related literature

For the development of colorimetric chemosensors, see: Coll et al. (2007 ▶); Evans et al. (2006 ▶). For similar deprotonation reactions, see: Kang et al. (2009 ▶).

Experimental

Crystal data

C16H36N+·C14H8N3O3S−

M = 540.75

Monoclinic,

a = 7.9234 (7) Å

b = 25.059 (2) Å

c = 15.4916 (14) Å

β = 97.699 (2)°

V = 3048.2 (5) Å3

Z = 4

Mo Kα radiation

μ = 0.14 mm−1

T = 223 K

0.22 × 0.11 × 0.10 mm

Data collection

Bruker SMART 1000 CCD diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2000 ▶) T min = 0.979, T max = 0.988

11371 measured reflections

5730 independent reflections

2547 reflections with I > 2σ(I)

R int = 0.076

Refinement

R[F 2 > 2σ(F 2)] = 0.069

wR(F 2) = 0.169

S = 0.95

5730 reflections

347 parameters

2 restraints

H-atom parameters constrained

Δρmax = 0.25 e Å−3

Δρmin = −0.19 e Å−3

Absolute structure: Flack (1983 ▶), 1908 Friedel pairs

Flack parameter: 0.08 (12)

Data collection: SMART (Bruker, 2000 ▶); cell refinement: SAINT (Bruker, 2000 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: ORTEP-3 (Farrugia, 1997 ▶) and PLATON (Spek, 2009 ▶); software used to prepare material for publication: SHELXL97.

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536810026504/lx2157sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536810026504/lx2157Isup2.hkl

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

C16H36N+·C14H8N3O3S−	F(000) = 1168
Mr = 540.75	Dx = 1.178 Mg m−3
Monoclinic, Cc	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: C -2yc	Cell parameters from 1597 reflections
a = 7.9234 (7) Å	θ = 2.7–19.4°
b = 25.059 (2) Å	µ = 0.14 mm−1
c = 15.4916 (14) Å	T = 223 K
β = 97.699 (2)°	Block, yellow
V = 3048.2 (5) Å3	0.22 × 0.11 × 0.10 mm
Z = 4

Bruker SMART 1000 CCD diffractometer	5730 independent reflections
Radiation source: fine-focus sealed tube	2547 reflections with I > 2σ(I)
graphite	Rint = 0.076
φ and ω scans	θmax = 28.3°, θmin = 2.1°
Absorption correction: multi-scan (SADABS; Bruker, 2000)	h = −9→10
Tmin = 0.979, Tmax = 0.988	k = −33→29
11371 measured reflections	l = −19→20

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)] = 0.069	H-atom parameters constrained
wR(F2) = 0.169	w = 1/[σ2(Fo2) + (0.0566P)2] where P = (Fo2 + 2Fc2)/3
S = 0.95	(Δ/σ)max < 0.001
5730 reflections	Δρmax = 0.25 e Å−3
347 parameters	Δρmin = −0.19 e Å−3
2 restraints	Absolute structure: Flack (1983), 1908 Friedel pairs
Primary atom site location: structure-invariant direct methods	Flack parameter: 0.08 (12)

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	0.70508 (16)	0.32664 (5)	0.33449 (9)	0.0502 (4)
O1	0.6825 (5)	0.22458 (14)	0.3155 (3)	0.0623 (11)
O2	0.8146 (9)	0.57535 (19)	0.3706 (4)	0.131 (2)
O3	0.8142 (7)	0.52224 (19)	0.4779 (4)	0.0984 (16)
N1	0.6279 (5)	0.26786 (17)	0.1823 (3)	0.0505 (11)
N2	0.6516 (5)	0.36006 (18)	0.1718 (3)	0.0521 (11)
N3	0.7979 (7)	0.5308 (2)	0.3993 (5)	0.0829 (16)
C1	0.6094 (7)	0.1727 (2)	0.1884 (4)	0.0573 (15)
C2	0.6156 (8)	0.1257 (2)	0.2357 (5)	0.0767 (19)
H2	0.6405	0.1272	0.2967	0.092*
C3	0.5860 (10)	0.0768 (3)	0.1957 (6)	0.102 (3)
H3	0.5866	0.0454	0.2290	0.123*
C4	0.5553 (9)	0.0746 (3)	0.1050 (7)	0.099 (3)
H4	0.5379	0.0415	0.0767	0.119*
C5	0.5504 (9)	0.1211 (3)	0.0569 (5)	0.088 (2)
H5	0.5319	0.1197	−0.0043	0.106*
C6	0.5723 (7)	0.1689 (2)	0.0985 (4)	0.0640 (16)
H6	0.5621	0.2004	0.0652	0.077*
C7	0.6423 (6)	0.2240 (2)	0.2350 (4)	0.0521 (14)
C8	0.6573 (6)	0.3158 (2)	0.2190 (3)	0.0472 (14)
C9	0.7132 (6)	0.3942 (2)	0.3138 (3)	0.0457 (13)
C10	0.7471 (7)	0.4359 (2)	0.3727 (4)	0.0544 (14)
H10	0.7650	0.4295	0.4330	0.065*
C11	0.7536 (7)	0.4870 (2)	0.3401 (4)	0.0628 (17)
C12	0.7267 (8)	0.4976 (2)	0.2513 (5)	0.0748 (19)
H12	0.7319	0.5329	0.2311	0.090*
C13	0.6920 (8)	0.4558 (2)	0.1925 (4)	0.0687 (17)
H13	0.6745	0.4625	0.1322	0.082*
C14	0.6833 (6)	0.4036 (2)	0.2238 (4)	0.0486 (13)
N4	0.1005 (5)	0.30363 (16)	0.0850 (3)	0.0481 (10)
C15	0.2355 (7)	0.3308 (2)	0.0382 (4)	0.0585 (15)
H15A	0.3473	0.3244	0.0721	0.070*
H15B	0.2356	0.3136	−0.0185	0.070*
C16	0.2155 (8)	0.3893 (2)	0.0237 (4)	0.080 (2)
H16A	0.2158	0.4073	0.0799	0.096*
H16B	0.1058	0.3964	−0.0116	0.096*
C17	0.3571 (8)	0.4115 (3)	−0.0218 (5)	0.093 (2)
H17A	0.3565	0.3932	−0.0777	0.111*
H17B	0.4665	0.4040	0.0137	0.111*
C18	0.3428 (11)	0.4709 (3)	−0.0380 (8)	0.179 (5)
H18A	0.3498	0.4896	0.0173	0.268*
H18B	0.2345	0.4788	−0.0727	0.268*
H18C	0.4350	0.4826	−0.0689	0.268*
C19	0.0817 (6)	0.3310 (2)	0.1697 (3)	0.0524 (14)
H19A	−0.0017	0.3112	0.1984	0.063*
H19B	0.0352	0.3668	0.1567	0.063*
C20	0.2431 (7)	0.3364 (2)	0.2329 (4)	0.0604 (15)
H20A	0.3298	0.3548	0.2044	0.073*
H20B	0.2866	0.3008	0.2503	0.073*
C21	0.2101 (9)	0.3676 (3)	0.3135 (4)	0.0762 (19)
H21A	0.1071	0.3534	0.3338	0.091*
H21B	0.3053	0.3615	0.3597	0.091*
C22	0.1894 (11)	0.4244 (3)	0.3004 (6)	0.117 (3)
H22A	0.2898	0.4389	0.2793	0.176*
H22B	0.1744	0.4413	0.3551	0.176*
H22C	0.0902	0.4311	0.2579	0.176*
C23	0.1534 (6)	0.2459 (2)	0.0986 (4)	0.0578 (15)
H23A	0.2673	0.2450	0.1322	0.069*
H23B	0.1620	0.2300	0.0415	0.069*
C24	0.0357 (7)	0.21084 (19)	0.1452 (5)	0.0713 (19)
H24A	0.0326	0.2249	0.2040	0.086*
H24B	−0.0800	0.2128	0.1138	0.086*
C25	0.0915 (9)	0.1527 (3)	0.1516 (6)	0.100 (2)
H25A	0.2143	0.1517	0.1711	0.120*
H25B	0.0349	0.1355	0.1967	0.120*
C26	0.0580 (11)	0.1222 (3)	0.0743 (6)	0.130 (3)
H26A	0.1130	0.1388	0.0288	0.195*
H26B	−0.0639	0.1207	0.0562	0.195*
H26C	0.1020	0.0864	0.0850	0.195*
C27	−0.0763 (6)	0.3079 (2)	0.0309 (3)	0.0546 (14)
H27A	−0.1613	0.2942	0.0657	0.066*
H27B	−0.1017	0.3457	0.0191	0.066*
C28	−0.0946 (8)	0.2782 (3)	−0.0552 (4)	0.095 (2)
H28A	0.0029	0.2864	−0.0857	0.114*
H28B	−0.0947	0.2397	−0.0441	0.114*
C29	−0.2574 (10)	0.2935 (3)	−0.1122 (5)	0.098 (2)
H29A	−0.2581	0.3323	−0.1199	0.117*
H29B	−0.2560	0.2773	−0.1697	0.117*
C30	−0.4061 (10)	0.2790 (4)	−0.0820 (5)	0.132 (3)
H30A	−0.4054	0.2921	−0.0231	0.198*
H30B	−0.4159	0.2404	−0.0824	0.198*
H30C	−0.5021	0.2942	−0.1194	0.198*

	U11	U22	U33	U12	U13	U23
S1	0.0514 (8)	0.0594 (7)	0.0391 (7)	0.0010 (8)	0.0035 (6)	0.0034 (7)
O1	0.078 (3)	0.066 (2)	0.042 (3)	−0.003 (2)	0.006 (2)	0.003 (2)
O2	0.220 (7)	0.058 (3)	0.109 (5)	−0.020 (3)	0.003 (4)	−0.002 (3)
O3	0.130 (5)	0.089 (3)	0.073 (4)	0.000 (3)	0.000 (3)	−0.023 (3)
N1	0.050 (3)	0.059 (3)	0.044 (3)	0.003 (2)	0.008 (2)	−0.001 (2)
N2	0.050 (3)	0.062 (3)	0.044 (3)	0.002 (2)	0.004 (2)	0.006 (2)
N3	0.095 (4)	0.071 (4)	0.079 (5)	−0.004 (3)	−0.001 (3)	−0.008 (4)
C1	0.045 (3)	0.065 (4)	0.063 (4)	−0.001 (3)	0.007 (3)	−0.001 (4)
C2	0.090 (5)	0.054 (4)	0.082 (5)	−0.015 (3)	−0.001 (4)	−0.008 (4)
C3	0.124 (7)	0.068 (5)	0.110 (8)	−0.012 (4)	0.001 (6)	0.006 (5)
C4	0.091 (6)	0.097 (6)	0.108 (7)	−0.029 (5)	0.010 (5)	−0.031 (6)
C5	0.094 (6)	0.096 (5)	0.076 (5)	−0.016 (4)	0.016 (4)	−0.030 (5)
C6	0.056 (4)	0.074 (4)	0.060 (4)	−0.004 (3)	0.004 (3)	−0.012 (4)
C7	0.034 (3)	0.066 (4)	0.057 (4)	0.002 (3)	0.012 (3)	−0.001 (3)
C8	0.033 (3)	0.069 (4)	0.041 (3)	0.006 (3)	0.009 (2)	0.005 (3)
C9	0.038 (3)	0.059 (3)	0.041 (4)	−0.003 (3)	0.004 (3)	0.001 (3)
C10	0.050 (3)	0.063 (4)	0.049 (4)	0.005 (3)	0.003 (3)	0.002 (3)
C11	0.071 (5)	0.052 (3)	0.064 (4)	0.000 (3)	0.005 (4)	−0.011 (4)
C12	0.091 (5)	0.062 (4)	0.069 (5)	0.007 (3)	0.001 (4)	0.014 (4)
C13	0.084 (5)	0.061 (4)	0.059 (4)	−0.003 (3)	0.001 (3)	0.010 (3)
C14	0.044 (3)	0.054 (3)	0.048 (4)	0.007 (3)	0.002 (3)	0.008 (3)
N4	0.035 (2)	0.068 (3)	0.041 (3)	0.004 (2)	0.0049 (19)	−0.007 (2)
C15	0.048 (3)	0.075 (4)	0.054 (4)	−0.003 (3)	0.011 (3)	−0.001 (3)
C16	0.061 (4)	0.100 (5)	0.081 (5)	0.008 (4)	0.017 (4)	0.031 (4)
C17	0.057 (4)	0.128 (6)	0.089 (6)	−0.023 (4)	−0.002 (4)	0.039 (5)
C18	0.107 (8)	0.141 (7)	0.284 (15)	−0.005 (6)	0.013 (8)	0.150 (9)
C19	0.044 (3)	0.071 (3)	0.043 (3)	0.001 (3)	0.007 (3)	−0.005 (3)
C20	0.049 (3)	0.073 (4)	0.058 (4)	−0.006 (3)	0.003 (3)	−0.003 (3)
C21	0.064 (4)	0.105 (5)	0.056 (5)	−0.006 (4)	−0.003 (3)	−0.023 (4)
C22	0.101 (6)	0.095 (5)	0.154 (10)	−0.012 (5)	0.011 (6)	−0.050 (6)
C23	0.038 (3)	0.057 (3)	0.076 (4)	0.005 (3)	0.000 (3)	−0.005 (3)
C24	0.051 (4)	0.058 (3)	0.103 (6)	−0.002 (3)	0.004 (4)	0.006 (4)
C25	0.079 (5)	0.090 (5)	0.127 (8)	0.000 (4)	−0.003 (5)	0.003 (5)
C26	0.134 (8)	0.134 (6)	0.111 (8)	0.058 (6)	−0.027 (6)	−0.051 (6)
C27	0.038 (3)	0.081 (4)	0.044 (3)	0.007 (3)	0.000 (2)	−0.006 (3)
C28	0.058 (4)	0.175 (7)	0.048 (4)	0.002 (4)	−0.008 (3)	−0.024 (4)
C29	0.094 (6)	0.125 (6)	0.067 (5)	−0.027 (5)	−0.014 (4)	−0.006 (5)
C30	0.069 (5)	0.238 (11)	0.084 (6)	0.004 (6)	−0.012 (4)	−0.033 (7)

S1—C9	1.725 (5)	C17—H17A	0.9800
S1—C8	1.799 (5)	C17—H17B	0.9800
O1—C7	1.245 (6)	C18—H18A	0.9700
O2—N3	1.216 (7)	C18—H18B	0.9700
O3—N3	1.226 (7)	C18—H18C	0.9700
N1—C8	1.335 (6)	C19—C20	1.509 (7)
N1—C7	1.365 (7)	C19—H19A	0.9800
N2—C8	1.327 (6)	C19—H19B	0.9800
N2—C14	1.360 (7)	C20—C21	1.525 (8)
N3—C11	1.441 (7)	C20—H20A	0.9800
C1—C2	1.383 (8)	C20—H20B	0.9800
C1—C6	1.388 (8)	C21—C22	1.444 (8)
C1—C7	1.480 (7)	C21—H21A	0.9800
C2—C3	1.380 (8)	C21—H21B	0.9800
C2—H2	0.9400	C22—H22A	0.9700
C3—C4	1.394 (11)	C22—H22B	0.9700
C3—H3	0.9400	C22—H22C	0.9700
C4—C5	1.380 (10)	C23—C24	1.530 (7)
C4—H4	0.9400	C23—H23A	0.9800
C5—C6	1.361 (8)	C23—H23B	0.9800
C5—H5	0.9400	C24—C25	1.521 (8)
C6—H6	0.9400	C24—H24A	0.9800
C9—C10	1.390 (7)	C24—H24B	0.9800
C9—C14	1.402 (7)	C25—C26	1.415 (10)
C10—C11	1.381 (7)	C25—H25A	0.9800
C10—H10	0.9400	C25—H25B	0.9800
C11—C12	1.388 (8)	C26—H26A	0.9700
C12—C13	1.394 (8)	C26—H26B	0.9700
C12—H12	0.9400	C26—H26C	0.9700
C13—C14	1.398 (7)	C27—C28	1.517 (8)
C13—H13	0.9400	C27—H27A	0.9800
N4—C19	1.505 (6)	C27—H27B	0.9800
N4—C23	1.513 (6)	C28—C29	1.511 (9)
N4—C15	1.531 (6)	C28—H28A	0.9800
N4—C27	1.537 (6)	C28—H28B	0.9800
C15—C16	1.487 (7)	C29—C30	1.373 (9)
C15—H15A	0.9800	C29—H29A	0.9800
C15—H15B	0.9800	C29—H29B	0.9800
C16—C17	1.509 (8)	C30—H30A	0.9700
C16—H16A	0.9800	C30—H30B	0.9700
C16—H16B	0.9800	C30—H30C	0.9700
C17—C18	1.511 (9)
C9—S1—C8	88.4 (3)	C17—C18—H18C	109.5
C8—N1—C7	118.3 (5)	H18A—C18—H18C	109.5
C8—N2—C14	110.8 (5)	H18B—C18—H18C	109.5
O2—N3—O3	121.4 (7)	N4—C19—C20	115.6 (4)
O2—N3—C11	119.7 (7)	N4—C19—H19A	108.4
O3—N3—C11	118.9 (6)	C20—C19—H19A	108.4
C2—C1—C6	117.5 (6)	N4—C19—H19B	108.4
C2—C1—C7	119.3 (6)	C20—C19—H19B	108.4
C6—C1—C7	123.2 (5)	H19A—C19—H19B	107.4
C3—C2—C1	121.7 (7)	C19—C20—C21	110.7 (5)
C3—C2—H2	119.1	C19—C20—H20A	109.5
C1—C2—H2	119.1	C21—C20—H20A	109.5
C2—C3—C4	119.0 (7)	C19—C20—H20B	109.5
C2—C3—H3	120.5	C21—C20—H20B	109.5
C4—C3—H3	120.5	H20A—C20—H20B	108.1
C5—C4—C3	120.0 (7)	C22—C21—C20	114.8 (6)
C5—C4—H4	120.0	C22—C21—H21A	108.6
C3—C4—H4	120.0	C20—C21—H21A	108.6
C6—C5—C4	119.6 (8)	C22—C21—H21B	108.6
C6—C5—H5	120.2	C20—C21—H21B	108.6
C4—C5—H5	120.2	H21A—C21—H21B	107.5
C5—C6—C1	122.1 (6)	C21—C22—H22A	109.5
C5—C6—H6	118.9	C21—C22—H22B	109.5
C1—C6—H6	118.9	H22A—C22—H22B	109.5
O1—C7—N1	125.4 (6)	C21—C22—H22C	109.5
O1—C7—C1	120.2 (6)	H22A—C22—H22C	109.5
N1—C7—C1	114.4 (5)	H22B—C22—H22C	109.5
N2—C8—N1	121.7 (5)	N4—C23—C24	116.1 (4)
N2—C8—S1	114.1 (4)	N4—C23—H23A	108.3
N1—C8—S1	124.2 (4)	C24—C23—H23A	108.3
C10—C9—C14	121.2 (5)	N4—C23—H23B	108.3
C10—C9—S1	128.6 (4)	C24—C23—H23B	108.3
C14—C9—S1	110.2 (4)	H23A—C23—H23B	107.4
C11—C10—C9	118.1 (5)	C25—C24—C23	113.0 (5)
C11—C10—H10	120.9	C25—C24—H24A	109.0
C9—C10—H10	120.9	C23—C24—H24A	109.0
C10—C11—C12	122.1 (6)	C25—C24—H24B	109.0
C10—C11—N3	119.4 (6)	C23—C24—H24B	109.0
C12—C11—N3	118.5 (6)	H24A—C24—H24B	107.8
C11—C12—C13	119.6 (6)	C26—C25—C24	116.2 (7)
C11—C12—H12	120.2	C26—C25—H25A	108.2
C13—C12—H12	120.2	C24—C25—H25A	108.2
C12—C13—C14	119.4 (6)	C26—C25—H25B	108.2
C12—C13—H13	120.3	C24—C25—H25B	108.2
C14—C13—H13	120.3	H25A—C25—H25B	107.4
N2—C14—C13	123.9 (5)	C25—C26—H26A	109.5
N2—C14—C9	116.5 (5)	C25—C26—H26B	109.5
C13—C14—C9	119.6 (6)	H26A—C26—H26B	109.5
C19—N4—C23	111.9 (4)	C25—C26—H26C	109.5
C19—N4—C15	111.5 (4)	H26A—C26—H26C	109.5
C23—N4—C15	107.1 (4)	H26B—C26—H26C	109.5
C19—N4—C27	104.7 (4)	C28—C27—N4	114.7 (4)
C23—N4—C27	111.0 (4)	C28—C27—H27A	108.6
C15—N4—C27	110.7 (4)	N4—C27—H27A	108.6
C16—C15—N4	116.3 (4)	C28—C27—H27B	108.6
C16—C15—H15A	108.2	N4—C27—H27B	108.6
N4—C15—H15A	108.2	H27A—C27—H27B	107.6
C16—C15—H15B	108.2	C29—C28—C27	111.3 (6)
N4—C15—H15B	108.2	C29—C28—H28A	109.4
H15A—C15—H15B	107.4	C27—C28—H28A	109.4
C15—C16—C17	111.3 (5)	C29—C28—H28B	109.4
C15—C16—H16A	109.4	C27—C28—H28B	109.4
C17—C16—H16A	109.4	H28A—C28—H28B	108.0
C15—C16—H16B	109.4	C30—C29—C28	116.0 (7)
C17—C16—H16B	109.4	C30—C29—H29A	108.3
H16A—C16—H16B	108.0	C28—C29—H29A	108.3
C16—C17—C18	113.4 (6)	C30—C29—H29B	108.3
C16—C17—H17A	108.9	C28—C29—H29B	108.3
C18—C17—H17A	108.9	H29A—C29—H29B	107.4
C16—C17—H17B	108.9	C29—C30—H30A	109.5
C18—C17—H17B	108.9	C29—C30—H30B	109.5
H17A—C17—H17B	107.7	H30A—C30—H30B	109.5
C17—C18—H18A	109.5	C29—C30—H30C	109.5
C17—C18—H18B	109.5	H30A—C30—H30C	109.5
H18A—C18—H18B	109.5	H30B—C30—H30C	109.5
C6—C1—C2—C3	−0.1 (9)	N3—C11—C12—C13	176.9 (6)
C7—C1—C2—C3	−179.9 (6)	C11—C12—C13—C14	0.5 (9)
C1—C2—C3—C4	2.4 (11)	C8—N2—C14—C13	177.6 (5)
C2—C3—C4—C5	−1.7 (12)	C8—N2—C14—C9	−0.6 (6)
C3—C4—C5—C6	−1.3 (11)	C12—C13—C14—N2	−179.4 (5)
C4—C5—C6—C1	3.7 (10)	C12—C13—C14—C9	−1.3 (8)
C2—C1—C6—C5	−3.0 (8)	C10—C9—C14—N2	179.9 (5)
C7—C1—C6—C5	176.9 (5)	S1—C9—C14—N2	1.2 (6)
C8—N1—C7—O1	−0.6 (7)	C10—C9—C14—C13	1.7 (8)
C8—N1—C7—C1	−179.3 (4)	S1—C9—C14—C13	−177.1 (4)
C2—C1—C7—O1	3.1 (8)	C19—N4—C15—C16	−53.1 (6)
C6—C1—C7—O1	−176.7 (5)	C23—N4—C15—C16	−175.8 (5)
C2—C1—C7—N1	−178.1 (5)	C27—N4—C15—C16	63.1 (6)
C6—C1—C7—N1	2.0 (7)	N4—C15—C16—C17	179.3 (6)
C14—N2—C8—N1	179.1 (4)	C15—C16—C17—C18	−179.9 (7)
C14—N2—C8—S1	−0.3 (5)	C23—N4—C19—C20	64.5 (5)
C7—N1—C8—N2	177.6 (4)	C15—N4—C19—C20	−55.4 (6)
C7—N1—C8—S1	−3.1 (6)	C27—N4—C19—C20	−175.2 (5)
C9—S1—C8—N2	0.8 (4)	N4—C19—C20—C21	176.5 (5)
C9—S1—C8—N1	−178.5 (4)	C19—C20—C21—C22	−74.8 (7)
C8—S1—C9—C10	−179.7 (5)	C19—N4—C23—C24	57.3 (6)
C8—S1—C9—C14	−1.0 (4)	C15—N4—C23—C24	179.7 (5)
C14—C9—C10—C11	−1.2 (8)	C27—N4—C23—C24	−59.3 (6)
S1—C9—C10—C11	177.3 (4)	N4—C23—C24—C25	176.6 (5)
C9—C10—C11—C12	0.4 (8)	C23—C24—C25—C26	−75.7 (8)
C9—C10—C11—N3	−176.5 (5)	C19—N4—C27—C28	−174.3 (5)
O2—N3—C11—C10	175.3 (6)	C23—N4—C27—C28	−53.4 (6)
O3—N3—C11—C10	−6.4 (9)	C15—N4—C27—C28	65.4 (6)
O2—N3—C11—C12	−1.7 (9)	N4—C27—C28—C29	−168.3 (5)
O3—N3—C11—C12	176.6 (6)	C27—C28—C29—C30	−65.9 (9)
C10—C11—C12—C13	−0.1 (9)

D—H···A	D—H	H···A	D···A	D—H···A
C28—H28A···O1i	0.98	2.24	3.166 (8)	157
C29—H29A···O2ii	0.98	2.39	3.353 (9)	166

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C28—H28A⋯O1i	0.98	2.24	3.166 (8)	157
C29—H29A⋯O2ii	0.98	2.39	3.353 (9)	166

Symmetry codes: (i) ; (ii) .