3,3'-Di-2-naphthoyl-1,1'-(o-phenyl-ene)dithio-urea.

In the mol-ecule of the title compound, C(30)H(22)N(4)O(2)S(2), the central benzene ring is oriented at dihedral angles of 63.83 (3) and 1.37 (3)° with respect to the naphthalene ring systems, while the two naphthalene ring systems are oriented at a dihedral angle of 62.78 (3)°. Intra-molecular N-H⋯O and N-H⋯N hydrogen bonds result in the formation of one five- and two six-membered rings. The twisting modes of the two side arms are different [C-N-C-O and C-N-C-N torsion angles = 11.1 (4) and 1.5 (3)°, respectively, in one arm, and -2.2 (4) and 0.8 (3)° in the other arm]. In the crystal structure, inter-molecular N-H⋯S hydrogen bonds link the mol-ecules into centrosymmetric dimers. There is a C-H⋯π contact between the naphthalene rings and π-π contacts between the naphthalene rings and the naphthalene and benzene rings [centroid-centroid distances = 3.651 (1), 3.828 (1), 3.811 (2) and 3.786 (1) Å].

Related literature

For a related structure, see: Thiam et al. (2008 ▶). For ring conformation puckering parameters, see: Cremer & Pople (1975 ▶).

Experimental

Crystal data

C30H22N4O2S2

M = 534.64

Triclinic,

a = 8.7135 (17) Å

b = 12.453 (3) Å

c = 12.541 (3) Å

α = 72.33 (3)°

β = 74.55 (3)°

γ = 78.89 (3)°

V = 1240.5 (6) Å3

Z = 2

Mo Kα radiation

μ = 0.25 mm−1

T = 113 (2) K

0.10 × 0.08 × 0.04 mm

Data collection

Rigaku Saturn CCD area-detector diffractometer

Absorption correction: multi-scan (CrystalClear; Rigaku/MSC, 2005 ▶) T min = 0.975, T max = 0.990

7203 measured reflections

4337 independent reflections

3311 reflections with I > 2σ(I)

R int = 0.055

Refinement

R[F 2 > 2σ(F 2)] = 0.050

wR(F 2) = 0.130

S = 1.07

4337 reflections

355 parameters

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.32 e Å−3

Δρmin = −0.38 e Å−3

Data collection: CrystalClear (Rigaku/MSC, 2005 ▶); cell refinement: CrystalClear; data reduction: CrystalStructure (Rigaku/MSC, 2005 ▶); 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 I, global. DOI: 10.1107/S1600536808026299/hk2511sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536808026299/hk2511Isup2.hkl

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

C30H22N4O2S2	Z = 2
Mr = 534.64	F000 = 556
Triclinic, P1	Dx = 1.431 Mg m−3
Hall symbol: -P 1	Melting point: 489 K
a = 8.7135 (17) Å	Mo Kα radiation λ = 0.71073 Å
b = 12.453 (3) Å	Cell parameters from 2566 reflections
c = 12.541 (3) Å	θ = 1.7–27.1º
α = 72.33 (3)º	µ = 0.25 mm−1
β = 74.55 (3)º	T = 113 (2) K
γ = 78.89 (3)º	Block, colorless
V = 1240.5 (6) Å3	0.10 × 0.08 × 0.04 mm

Rigaku Saturn CCD area-detector diffractometer	4337 independent reflections
Radiation source: rotating anode	3311 reflections with I > 2σ(I)
Monochromator: confocal	Rint = 0.055
Detector resolution: 7.31 pixels mm-1	θmax = 25.0º
T = 113(2) K	θmin = 1.7º
ω and φ scans	h = −9→10
Absorption correction: multi-scan(CrystalClear; Rigaku/MSC, 2005)	k = −14→14
Tmin = 0.975, Tmax = 0.990	l = −14→12
7203 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)] = 0.050	H atoms treated by a mixture of independent and constrained refinement
wR(F2) = 0.130	w = 1/[σ2(Fo2) + (0.0613P)2] where P = (Fo2 + 2Fc2)/3
S = 1.07	(Δ/σ)max = 0.001
4337 reflections	Δρmax = 0.32 e Å−3
355 parameters	Δρmin = −0.38 e Å−3
Primary atom site location: structure-invariant direct methods	Extinction correction: none

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 > 2sigma(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	0.14334 (7)	1.12794 (6)	0.94643 (6)	0.02210 (19)
S2	0.47504 (8)	1.33865 (7)	0.40927 (6)	0.0302 (2)
O1	0.48084 (19)	0.83813 (16)	0.82983 (16)	0.0242 (4)
O2	0.30123 (19)	1.00328 (16)	0.63446 (14)	0.0231 (4)
N1	0.4251 (2)	1.05227 (19)	0.83207 (17)	0.0178 (5)
H1	0.488 (3)	0.992 (2)	0.814 (2)	0.021*
N2	0.2372 (2)	0.92516 (18)	0.90634 (17)	0.0179 (5)
H2A	0.146 (3)	0.911 (2)	0.941 (2)	0.021*
N3	0.4218 (2)	1.1856 (2)	0.61854 (19)	0.0199 (5)
H3A	0.384 (3)	1.124 (3)	0.650 (3)	0.024*
N4	0.3551 (2)	1.1461 (2)	0.47074 (19)	0.0223 (5)
H4A	0.356 (3)	1.171 (3)	0.397 (3)	0.027*
C1	0.4825 (2)	1.2304 (2)	0.6873 (2)	0.0173 (5)
C2	0.5430 (3)	1.3339 (2)	0.6541 (2)	0.0219 (6)
H2	0.5435	1.3827	0.5792	0.026*
C3	0.6027 (3)	1.3653 (2)	0.7308 (2)	0.0219 (6)
H3	0.6460	1.4353	0.7075	0.026*
C4	0.6001 (3)	1.2962 (2)	0.8410 (2)	0.0240 (6)
H4	0.6407	1.3192	0.8927	0.029*
C5	0.5384 (3)	1.1938 (2)	0.8755 (2)	0.0221 (6)
H5	0.5356	1.1465	0.9512	0.026*
C6	0.4806 (3)	1.1607 (2)	0.7992 (2)	0.0172 (5)
C7	0.2774 (3)	1.0316 (2)	0.8916 (2)	0.0168 (5)
C8	0.3352 (3)	0.8358 (2)	0.8680 (2)	0.0178 (5)
C9	0.2575 (3)	0.7382 (2)	0.8759 (2)	0.0181 (5)
C10	0.1037 (3)	0.7483 (2)	0.86101 (19)	0.0175 (5)
H10	0.0395	0.8199	0.8535	0.021*
C11	0.0400 (3)	0.6543 (2)	0.8567 (2)	0.0187 (5)
C12	−0.1169 (3)	0.6634 (2)	0.8383 (2)	0.0252 (6)
H12	−0.1859	0.7327	0.8362	0.030*
C13	−0.1691 (3)	0.5734 (3)	0.8237 (2)	0.0302 (7)
H13	−0.2731	0.5810	0.8098	0.036*
C14	−0.0691 (3)	0.4691 (3)	0.8292 (2)	0.0317 (7)
H14	−0.1058	0.4072	0.8179	0.038*
C15	0.0794 (3)	0.4564 (2)	0.8507 (2)	0.0286 (7)
H15	0.1444	0.3852	0.8560	0.034*
C16	0.1376 (3)	0.5477 (2)	0.8651 (2)	0.0213 (6)
C17	0.2939 (3)	0.5386 (2)	0.8852 (2)	0.0228 (6)
H17	0.3583	0.4670	0.8957	0.027*
C18	0.3520 (3)	0.6298 (2)	0.8896 (2)	0.0217 (6)
H18	0.4571	0.6217	0.9019	0.026*
C19	0.4172 (3)	1.2218 (2)	0.5070 (2)	0.0191 (6)
C20	0.2990 (3)	1.0445 (2)	0.5323 (2)	0.0198 (6)
C21	0.2338 (3)	0.9850 (2)	0.4698 (2)	0.0182 (6)
C22	0.2170 (3)	1.0319 (2)	0.3545 (2)	0.0214 (6)
H22	0.2506	1.1039	0.3120	0.026*
C23	0.1522 (3)	0.9726 (2)	0.3048 (2)	0.0247 (6)
H23	0.1422	1.0042	0.2275	0.030*
C24	0.0999 (3)	0.8658 (2)	0.3658 (2)	0.0235 (6)
C25	0.0246 (3)	0.8052 (3)	0.3189 (2)	0.0284 (7)
H25	0.0109	0.8356	0.2423	0.034*
C26	−0.0282 (3)	0.7038 (3)	0.3824 (3)	0.0317 (7)
H26	−0.0808	0.6655	0.3501	0.038*
C27	−0.0059 (3)	0.6551 (3)	0.4952 (3)	0.0316 (7)
H27	−0.0426	0.5841	0.5384	0.038*
C28	0.0691 (3)	0.7109 (3)	0.5422 (2)	0.0280 (7)
H28	0.0869	0.6770	0.6174	0.034*
C29	0.1199 (3)	0.8177 (2)	0.4805 (2)	0.0201 (6)
C30	0.1876 (3)	0.8804 (2)	0.5296 (2)	0.0203 (6)
H30	0.2012	0.8490	0.6060	0.024*

	U11	U22	U33	U12	U13	U23
S1	0.0227 (3)	0.0185 (4)	0.0251 (3)	−0.0060 (3)	0.0016 (2)	−0.0097 (3)
S2	0.0430 (4)	0.0245 (5)	0.0217 (4)	−0.0143 (3)	−0.0095 (3)	0.0041 (3)
O1	0.0205 (9)	0.0215 (12)	0.0295 (10)	−0.0025 (7)	−0.0020 (7)	−0.0084 (9)
O2	0.0329 (10)	0.0215 (12)	0.0157 (9)	−0.0084 (8)	−0.0052 (7)	−0.0030 (9)
N1	0.0202 (10)	0.0148 (13)	0.0186 (10)	−0.0048 (9)	−0.0026 (8)	−0.0046 (10)
N2	0.0182 (9)	0.0161 (13)	0.0189 (10)	−0.0071 (9)	0.0011 (8)	−0.0053 (10)
N3	0.0232 (10)	0.0165 (14)	0.0209 (11)	−0.0080 (9)	−0.0033 (8)	−0.0042 (10)
N4	0.0297 (11)	0.0214 (14)	0.0155 (11)	−0.0066 (9)	−0.0040 (9)	−0.0031 (10)
C1	0.0167 (11)	0.0154 (15)	0.0191 (12)	−0.0041 (10)	−0.0018 (9)	−0.0039 (11)
C2	0.0220 (12)	0.0178 (16)	0.0232 (13)	−0.0021 (10)	−0.0036 (10)	−0.0029 (12)
C3	0.0199 (12)	0.0147 (16)	0.0309 (14)	−0.0049 (10)	−0.0019 (10)	−0.0072 (12)
C4	0.0238 (12)	0.0221 (17)	0.0289 (14)	−0.0046 (11)	−0.0067 (10)	−0.0091 (13)
C5	0.0231 (12)	0.0234 (17)	0.0199 (13)	−0.0059 (11)	−0.0037 (10)	−0.0051 (12)
C6	0.0157 (11)	0.0130 (15)	0.0220 (12)	−0.0036 (9)	0.0002 (9)	−0.0061 (11)
C7	0.0194 (11)	0.0193 (16)	0.0121 (11)	−0.0046 (10)	−0.0051 (9)	−0.0022 (11)
C8	0.0222 (12)	0.0156 (15)	0.0150 (11)	−0.0025 (10)	−0.0052 (9)	−0.0023 (11)
C9	0.0242 (12)	0.0149 (15)	0.0122 (11)	−0.0052 (10)	0.0012 (9)	−0.0021 (11)
C10	0.0219 (11)	0.0137 (15)	0.0143 (12)	−0.0014 (10)	−0.0022 (9)	−0.0022 (11)
C11	0.0242 (12)	0.0192 (16)	0.0116 (11)	−0.0073 (10)	−0.0002 (9)	−0.0030 (11)
C12	0.0253 (13)	0.0301 (18)	0.0209 (13)	−0.0062 (11)	−0.0044 (10)	−0.0070 (13)
C13	0.0243 (13)	0.046 (2)	0.0246 (14)	−0.0168 (12)	0.0006 (10)	−0.0136 (15)
C14	0.0381 (15)	0.035 (2)	0.0268 (15)	−0.0243 (13)	0.0089 (12)	−0.0161 (15)
C15	0.0372 (15)	0.0231 (18)	0.0237 (14)	−0.0118 (12)	0.0072 (11)	−0.0108 (13)
C16	0.0279 (13)	0.0179 (16)	0.0160 (12)	−0.0070 (10)	0.0037 (9)	−0.0062 (12)
C17	0.0255 (12)	0.0164 (16)	0.0214 (13)	0.0006 (11)	0.0019 (10)	−0.0060 (12)
C18	0.0220 (12)	0.0208 (16)	0.0186 (12)	−0.0014 (10)	−0.0009 (10)	−0.0037 (12)
C19	0.0211 (12)	0.0155 (15)	0.0201 (13)	−0.0038 (10)	−0.0033 (9)	−0.0038 (12)
C20	0.0183 (12)	0.0187 (16)	0.0202 (13)	−0.0028 (10)	−0.0007 (9)	−0.0048 (12)
C21	0.0189 (11)	0.0175 (16)	0.0162 (12)	−0.0008 (10)	−0.0011 (9)	−0.0050 (12)
C22	0.0235 (12)	0.0180 (16)	0.0198 (13)	−0.0019 (10)	−0.0014 (10)	−0.0041 (12)
C23	0.0245 (12)	0.0300 (18)	0.0188 (13)	0.0060 (11)	−0.0063 (10)	−0.0095 (13)
C24	0.0153 (11)	0.0304 (18)	0.0263 (14)	0.0049 (11)	−0.0019 (10)	−0.0166 (13)
C25	0.0225 (12)	0.041 (2)	0.0274 (14)	0.0044 (12)	−0.0082 (11)	−0.0203 (15)
C26	0.0231 (13)	0.040 (2)	0.0413 (17)	−0.0027 (12)	−0.0042 (12)	−0.0284 (17)
C27	0.0287 (14)	0.033 (2)	0.0354 (16)	−0.0093 (12)	0.0038 (12)	−0.0188 (15)
C28	0.0298 (13)	0.0314 (19)	0.0235 (14)	−0.0078 (12)	0.0014 (11)	−0.0124 (14)
C29	0.0173 (11)	0.0248 (17)	0.0191 (12)	−0.0015 (10)	0.0015 (9)	−0.0125 (12)
C30	0.0213 (12)	0.0244 (17)	0.0149 (12)	−0.0017 (10)	−0.0006 (9)	−0.0085 (12)

S1—C7	1.677 (2)	C11—C12	1.424 (3)
S2—C19	1.657 (3)	C12—C13	1.364 (4)
O1—C8	1.234 (3)	C12—H12	0.9500
O2—C20	1.231 (3)	C13—C14	1.412 (4)
N1—C7	1.334 (3)	C13—H13	0.9500
N1—C6	1.427 (3)	C14—C15	1.362 (4)
N1—H1	0.89 (2)	C14—H14	0.9500
N2—C7	1.381 (3)	C15—C16	1.407 (4)
N2—C8	1.392 (3)	C15—H15	0.9500
N2—H2A	0.82 (3)	C16—C17	1.427 (3)
N3—C19	1.343 (3)	C17—C18	1.350 (4)
N3—C1	1.409 (3)	C17—H17	0.9500
N3—H3A	0.83 (3)	C18—H18	0.9500
N4—C20	1.372 (4)	C20—C21	1.496 (3)
N4—C19	1.405 (3)	C21—C30	1.367 (4)
N4—H4A	0.88 (3)	C21—C22	1.422 (3)
C1—C2	1.389 (4)	C22—C23	1.371 (3)
C1—C6	1.405 (4)	C22—H22	0.9500
C2—C3	1.387 (3)	C23—C24	1.412 (4)
C2—H2	0.9500	C23—H23	0.9500
C3—C4	1.385 (4)	C24—C25	1.418 (3)
C3—H3	0.9500	C24—C29	1.424 (4)
C4—C5	1.381 (4)	C25—C26	1.363 (4)
C4—H4	0.9500	C25—H25	0.9500
C5—C6	1.385 (3)	C26—C27	1.409 (4)
C5—H5	0.9500	C26—H26	0.9500
C8—C9	1.468 (3)	C27—C28	1.374 (4)
C9—C10	1.379 (3)	C27—H27	0.9500
C9—C18	1.427 (3)	C28—C29	1.409 (4)
C10—C11	1.409 (3)	C28—H28	0.9500
C10—H10	0.9500	C29—C30	1.414 (3)
C11—C16	1.423 (3)	C30—H30	0.9500
C7—N1—C6	123.9 (2)	C15—C14—C13	120.6 (3)
C7—N1—H1	114.4 (18)	C15—C14—H14	119.7
C6—N1—H1	121.7 (18)	C13—C14—H14	119.7
C7—N2—C8	127.1 (2)	C14—C15—C16	120.7 (3)
C7—N2—H2A	118.4 (19)	C14—C15—H15	119.7
C8—N2—H2A	114.5 (19)	C16—C15—H15	119.7
C19—N3—C1	131.8 (2)	C15—C16—C11	119.4 (2)
C19—N3—H3A	111.8 (19)	C15—C16—C17	122.4 (2)
C1—N3—H3A	116.4 (19)	C11—C16—C17	118.2 (2)
C20—N4—C19	129.6 (2)	C18—C17—C16	121.3 (2)
C20—N4—H4A	119.2 (19)	C18—C17—H17	119.4
C19—N4—H4A	111.2 (19)	C16—C17—H17	119.4
C2—C1—C6	119.0 (2)	C17—C18—C9	120.8 (2)
C2—C1—N3	126.2 (2)	C17—C18—H18	119.6
C6—C1—N3	114.8 (2)	C9—C18—H18	119.6
C3—C2—C1	119.5 (3)	N3—C19—N4	113.0 (2)
C3—C2—H2	120.2	N3—C19—S2	129.7 (2)
C1—C2—H2	120.2	N4—C19—S2	117.24 (19)
C4—C3—C2	121.1 (3)	O2—C20—N4	122.1 (2)
C4—C3—H3	119.5	O2—C20—C21	120.9 (2)
C2—C3—H3	119.5	N4—C20—C21	117.0 (2)
C5—C4—C3	120.0 (2)	C30—C21—C22	119.7 (2)
C5—C4—H4	120.0	C30—C21—C20	116.7 (2)
C3—C4—H4	120.0	C22—C21—C20	123.6 (2)
C4—C5—C6	119.5 (3)	C23—C22—C21	119.7 (3)
C4—C5—H5	120.2	C23—C22—H22	120.1
C6—C5—H5	120.2	C21—C22—H22	120.1
C5—C6—C1	120.9 (3)	C22—C23—C24	121.6 (2)
C5—C6—N1	119.9 (2)	C22—C23—H23	119.2
C1—C6—N1	119.2 (2)	C24—C23—H23	119.2
N1—C7—N2	116.73 (19)	C23—C24—C25	122.9 (3)
N1—C7—S1	123.0 (2)	C23—C24—C29	118.7 (2)
N2—C7—S1	120.30 (17)	C25—C24—C29	118.4 (3)
O1—C8—N2	121.6 (2)	C26—C25—C24	120.7 (3)
O1—C8—C9	121.5 (2)	C26—C25—H25	119.6
N2—C8—C9	116.90 (19)	C24—C25—H25	119.6
C10—C9—C18	119.0 (2)	C25—C26—C27	121.0 (2)
C10—C9—C8	123.1 (2)	C25—C26—H26	119.5
C18—C9—C8	117.6 (2)	C27—C26—H26	119.5
C9—C10—C11	121.3 (2)	C28—C27—C26	119.6 (3)
C9—C10—H10	119.4	C28—C27—H27	120.2
C11—C10—H10	119.4	C26—C27—H27	120.2
C10—C11—C16	119.3 (2)	C27—C28—C29	120.9 (3)
C10—C11—C12	122.2 (2)	C27—C28—H28	119.6
C16—C11—C12	118.4 (2)	C29—C28—H28	119.6
C13—C12—C11	120.6 (2)	C28—C29—C30	122.0 (2)
C13—C12—H12	119.7	C28—C29—C24	119.4 (2)
C11—C12—H12	119.7	C30—C29—C24	118.6 (3)
C12—C13—C14	120.3 (2)	C21—C30—C29	121.7 (2)
C12—C13—H13	119.9	C21—C30—H30	119.1
C14—C13—H13	119.9	C29—C30—H30	119.1
C19—N3—C1—C2	6.0 (4)	C10—C11—C16—C17	4.0 (3)
C19—N3—C1—C6	−173.4 (2)	C12—C11—C16—C17	−179.1 (2)
C6—C1—C2—C3	1.1 (3)	C15—C16—C17—C18	174.6 (2)
N3—C1—C2—C3	−178.3 (2)	C11—C16—C17—C18	−3.7 (4)
C1—C2—C3—C4	−1.3 (3)	C16—C17—C18—C9	1.0 (4)
C2—C3—C4—C5	0.5 (3)	C10—C9—C18—C17	1.6 (4)
C3—C4—C5—C6	0.5 (3)	C8—C9—C18—C17	−172.9 (2)
C4—C5—C6—C1	−0.6 (3)	C1—N3—C19—N4	175.7 (2)
C4—C5—C6—N1	176.5 (2)	C1—N3—C19—S2	−3.4 (4)
C2—C1—C6—C5	−0.2 (3)	C20—N4—C19—N3	0.8 (3)
N3—C1—C6—C5	179.30 (19)	C20—N4—C19—S2	−179.98 (18)
C2—C1—C6—N1	−177.28 (19)	C19—N4—C20—O2	−2.2 (4)
N3—C1—C6—N1	2.2 (3)	C19—N4—C20—C21	177.61 (19)
C7—N1—C6—C5	84.1 (3)	O2—C20—C21—C30	−4.2 (3)
C7—N1—C6—C1	−98.8 (3)	N4—C20—C21—C30	175.96 (18)
C6—N1—C7—N2	173.5 (2)	O2—C20—C21—C22	175.2 (2)
C6—N1—C7—S1	−6.2 (3)	N4—C20—C21—C22	−4.7 (3)
C8—N2—C7—N1	1.5 (3)	C30—C21—C22—C23	1.0 (3)
C8—N2—C7—S1	−178.83 (18)	C20—C21—C22—C23	−178.31 (18)
C7—N2—C8—O1	11.1 (4)	C21—C22—C23—C24	0.5 (3)
C7—N2—C8—C9	−169.4 (2)	C22—C23—C24—C25	176.6 (2)
O1—C8—C9—C10	−146.3 (2)	C22—C23—C24—C29	−1.9 (3)
N2—C8—C9—C10	34.2 (3)	C23—C24—C25—C26	−178.0 (2)
O1—C8—C9—C18	27.9 (3)	C29—C24—C25—C26	0.4 (3)
N2—C8—C9—C18	−151.6 (2)	C24—C25—C26—C27	−1.6 (3)
C18—C9—C10—C11	−1.3 (4)	C25—C26—C27—C28	0.5 (3)
C8—C9—C10—C11	172.9 (2)	C26—C27—C28—C29	1.8 (3)
C9—C10—C11—C16	−1.5 (4)	C27—C28—C29—C30	175.7 (2)
C9—C10—C11—C12	−178.3 (2)	C27—C28—C29—C24	−3.0 (3)
C10—C11—C12—C13	173.7 (2)	C23—C24—C29—C28	−179.69 (19)
C16—C11—C12—C13	−3.1 (4)	C25—C24—C29—C28	1.8 (3)
C11—C12—C13—C14	1.4 (4)	C23—C24—C29—C30	1.6 (3)
C12—C13—C14—C15	0.9 (4)	C25—C24—C29—C30	−176.88 (19)
C13—C14—C15—C16	−1.5 (4)	C22—C21—C30—C29	−1.3 (3)
C14—C15—C16—C11	−0.3 (4)	C20—C21—C30—C29	178.12 (18)
C14—C15—C16—C17	−178.6 (2)	C28—C29—C30—C21	−178.7 (2)
C10—C11—C16—C15	−174.4 (2)	C24—C29—C30—C21	−0.1 (3)
C12—C11—C16—C15	2.5 (4)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1···O1	0.89 (2)	1.88 (3)	2.624 (3)	140 (2)
N2—H2A···S1i	0.82 (3)	2.60 (3)	3.418 (2)	178 (2)
N3—H3A···O2	0.83 (3)	1.88 (3)	2.613 (3)	148 (3)
N3—H3A···N1	0.83 (3)	2.28 (3)	2.693 (3)	111 (2)
C28—H28···Cg3	0.95	2.76	3.621 (2)	152 (2)

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1⋯O1	0.89 (2)	1.88 (3)	2.624 (3)	140 (2)
N2—H2A⋯S1i	0.82 (3)	2.60 (3)	3.418 (2)	178 (2)
N3—H3A⋯O2	0.83 (3)	1.88 (3)	2.613 (3)	148 (3)
N3—H3A⋯N1	0.83 (3)	2.28 (3)	2.693 (3)	111 (2)
C28—H28⋯Cg3	0.95	2.76	3.621 (2)	152 (2)

Symmetry code: (i) . Cg3 is the centroid of the C11–C16 ring.