2-[5-(1,3-Benzodioxol-5-yl)-3-ferrocenyl-4,5-dihydro-1H-pyrazol-1-yl]-4-phenyl-1,3-thia-zole.

In the title compound, [Fe(C(5)H(5))(C(24)H(18)N(3)O(2)S)], the pyrazoline ring adopts a twist conformation. The thia-zole ring forms dihedral angles of 83.7 (2) and 34.4 (2)° with the benzene ring of the benzodioxole ring and the fused phenyl ring, respectively. The mol-ecular conformation is stabilized by an intra-molecular C-H⋯π inter-action. The crystal packing features inter-molecular C-H⋯N, C-H⋯O hydrogen bonds and weak C-H⋯π inter-actions.

Related literature

For the biological activity of ferrocenyl derivatives, see: Jaouen et al. (2004 ▶); Xie et al. (2008 ▶, 2010 ▶). For the crystal structures of pyrazoline derivatives, see: Gong et al. (2010 ▶). For puckering parameters, see: Cremer & Pople (1975 ▶).

Experimental

Crystal data

[Fe(C5H5)(C24H18N3O2S)]

M = 533.41

Triclinic,

a = 10.228 (5) Å

b = 11.018 (5) Å

c = 12.604 (6) Å

α = 107.776 (8)°

β = 100.416 (8)°

γ = 112.767 (7)°

V = 1172.7 (10) Å3

Z = 2

Mo Kα radiation

μ = 0.77 mm−1

T = 293 K

0.15 × 0.10 × 0.10 mm

Data collection

Bruker SMART area-detector diffractometer

Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ▶) T min = 0.894, T max = 0.927

6579 measured reflections

4716 independent reflections

3140 reflections with I > 2σ(I)

R int = 0.024

Refinement

R[F 2 > 2σ(F 2)] = 0.050

wR(F 2) = 0.124

S = 1.02

4716 reflections

325 parameters

H-atom parameters constrained

Δρmax = 0.30 e Å−3

Δρmin = −0.30 e Å−3

Data collection: SMART (Bruker, 2004 ▶); cell refinement: SAINT (Bruker, 2004 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXTL (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL.

Crystal structure: contains datablocks I, global. DOI: 10.1107/S160053681003638X/rz2480sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S160053681003638X/rz2480Isup2.hkl

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

[Fe(C5H5)(C24H18N3O2S)]	Z = 2
Mr = 533.41	F(000) = 552
Triclinic, P1	Dx = 1.511 Mg m−3
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 10.228 (5) Å	Cell parameters from 1390 reflections
b = 11.018 (5) Å	θ = 1.8–26.4°
c = 12.604 (6) Å	µ = 0.77 mm−1
α = 107.776 (8)°	T = 293 K
β = 100.416 (8)°	Block, yellow
γ = 112.767 (7)°	0.15 × 0.10 × 0.10 mm
V = 1172.7 (10) Å3

Bruker SMART area-detector diffractometer	4716 independent reflections
Radiation source: fine-focus sealed tube	3140 reflections with I > 2σ(I)
graphite	Rint = 0.024
phi and ω scans	θmax = 26.4°, θmin = 1.8°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −12→7
Tmin = 0.894, Tmax = 0.927	k = −13→13
6579 measured reflections	l = −13→15

Refinement on F2	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.050	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.124	H-atom parameters constrained
S = 1.02	w = 1/[σ2(Fo2) + (0.0498P)2 + 0.2299P] where P = (Fo2 + 2Fc2)/3
4716 reflections	(Δ/σ)max < 0.001
325 parameters	Δρmax = 0.30 e Å−3
0 restraints	Δρmin = −0.30 e Å−3

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
S2	0.23898 (10)	0.03306 (12)	0.18898 (8)	0.0590 (3)
Fe	0.13832 (5)	0.39165 (5)	0.68154 (4)	0.04547 (17)
O1	0.9205 (3)	0.6859 (3)	0.8659 (3)	0.0783 (9)
O2	0.8642 (3)	0.4884 (3)	0.9074 (2)	0.0666 (7)
N2	0.3592 (3)	0.1534 (3)	0.4240 (2)	0.0505 (7)
N3	0.2328 (3)	0.1739 (3)	0.4215 (2)	0.0439 (7)
N7	0.4875 (3)	0.0646 (3)	0.3137 (2)	0.0418 (6)
C1	0.7361 (4)	0.0552 (3)	0.2317 (3)	0.0442 (8)
H1	0.7617	0.1343	0.3008	0.053*
C2	0.8476 (4)	0.0314 (4)	0.1989 (3)	0.0528 (9)
H2	0.9483	0.0949	0.2451	0.063*
C3	0.8108 (4)	−0.0857 (4)	0.0984 (3)	0.0586 (10)
H3	0.8865	−0.1015	0.0758	0.070*
C4	0.6632 (4)	−0.1795 (4)	0.0311 (3)	0.0644 (11)
H4	0.6382	−0.2595	−0.0371	0.077*
C5	0.5519 (4)	−0.1557 (4)	0.0642 (3)	0.0546 (9)
H5	0.4514	−0.2211	0.0189	0.065*
C6	0.5863 (3)	−0.0368 (3)	0.1635 (3)	0.0387 (7)
C7	0.4688 (3)	−0.0038 (3)	0.1954 (3)	0.0404 (8)
C8	0.3423 (4)	−0.0305 (4)	0.1179 (3)	0.0526 (9)
H8	0.3140	−0.0774	0.0361	0.063*
C9	0.3752 (4)	0.0896 (3)	0.3212 (3)	0.0423 (8)
C10	0.2057 (3)	0.1734 (3)	0.5167 (3)	0.0368 (7)
C11	0.3027 (4)	0.1360 (3)	0.5895 (3)	0.0442 (8)
H11A	0.2493	0.0363	0.5788	0.053*
H11B	0.3392	0.1992	0.6729	0.053*
C12	0.4307 (4)	0.1597 (4)	0.5398 (3)	0.0429 (8)
H12	0.4559	0.0805	0.5287	0.051*
C13	0.5684 (4)	0.3028 (4)	0.6171 (3)	0.0425 (8)
C14	0.6077 (4)	0.4218 (4)	0.5902 (3)	0.0534 (10)
H14	0.5540	0.4115	0.5173	0.064*
C15	0.7264 (4)	0.5575 (4)	0.6701 (4)	0.0624 (11)
H15	0.7526	0.6377	0.6521	0.075*
C16	0.8005 (4)	0.5666 (4)	0.7735 (4)	0.0558 (10)
C17	0.7652 (4)	0.4490 (4)	0.8002 (3)	0.0476 (8)
C18	0.6510 (4)	0.3179 (4)	0.7253 (3)	0.0456 (8)
H18	0.6278	0.2392	0.7452	0.055*
C19	0.9424 (5)	0.6410 (4)	0.9566 (4)	0.0806 (13)
H19A	0.9047	0.6804	1.0165	0.097*
H19B	1.0491	0.6753	0.9936	0.097*
C20	0.0906 (3)	0.2054 (3)	0.5491 (3)	0.0410 (8)
C21	0.0226 (4)	0.2786 (4)	0.5058 (3)	0.0522 (9)
H21	0.0404	0.3125	0.4438	0.063*
C22	−0.0765 (4)	0.2935 (4)	0.5680 (3)	0.0586 (10)
H22	−0.1389	0.3405	0.5573	0.070*
C23	−0.0683 (4)	0.2303 (4)	0.6488 (3)	0.0560 (10)
H23	−0.1236	0.2266	0.7046	0.067*
C24	0.0342 (4)	0.1770 (3)	0.6385 (3)	0.0488 (9)
H24	0.0622	0.1282	0.6847	0.059*
C25	0.2947 (5)	0.5917 (4)	0.7109 (4)	0.0785 (13)
H25	0.3093	0.6292	0.6504	0.094*
C26	0.3654 (4)	0.5192 (4)	0.7469 (5)	0.0796 (14)
H26	0.4390	0.4969	0.7168	0.096*
C27	0.3135 (5)	0.4839 (4)	0.8335 (4)	0.0777 (13)
H27	0.3447	0.4328	0.8756	0.093*
C28	0.2109 (5)	0.5350 (4)	0.8506 (4)	0.0749 (13)
H28	0.1571	0.5258	0.9070	0.090*
C29	0.1981 (5)	0.6019 (4)	0.7753 (4)	0.0716 (12)
H29	0.1345	0.6486	0.7689	0.086*

	U11	U22	U33	U12	U13	U23
S2	0.0488 (5)	0.0842 (7)	0.0444 (6)	0.0376 (5)	0.0140 (4)	0.0201 (5)
Fe	0.0459 (3)	0.0395 (3)	0.0444 (3)	0.0177 (2)	0.0175 (2)	0.0112 (2)
O1	0.0593 (17)	0.0509 (17)	0.104 (2)	0.0132 (14)	0.0179 (17)	0.0294 (18)
O2	0.0615 (16)	0.0570 (17)	0.0603 (18)	0.0191 (13)	0.0054 (14)	0.0186 (14)
N2	0.0580 (18)	0.072 (2)	0.0386 (17)	0.0456 (17)	0.0207 (14)	0.0223 (15)
N3	0.0479 (16)	0.0520 (17)	0.0459 (17)	0.0342 (14)	0.0190 (14)	0.0220 (14)
N7	0.0450 (16)	0.0454 (16)	0.0366 (16)	0.0231 (13)	0.0151 (13)	0.0158 (13)
C1	0.049 (2)	0.0398 (19)	0.0386 (19)	0.0215 (16)	0.0115 (16)	0.0105 (15)
C2	0.046 (2)	0.053 (2)	0.058 (2)	0.0236 (18)	0.0164 (18)	0.0213 (19)
C3	0.058 (2)	0.066 (3)	0.063 (3)	0.041 (2)	0.026 (2)	0.022 (2)
C4	0.061 (2)	0.061 (3)	0.054 (2)	0.034 (2)	0.015 (2)	−0.001 (2)
C5	0.043 (2)	0.051 (2)	0.047 (2)	0.0168 (17)	0.0095 (17)	0.0027 (18)
C6	0.0452 (19)	0.0363 (17)	0.0375 (18)	0.0200 (15)	0.0158 (15)	0.0170 (15)
C7	0.0408 (19)	0.0402 (18)	0.0401 (19)	0.0170 (15)	0.0160 (15)	0.0181 (15)
C8	0.048 (2)	0.071 (3)	0.035 (2)	0.0311 (19)	0.0116 (16)	0.0149 (18)
C9	0.0450 (19)	0.047 (2)	0.042 (2)	0.0249 (16)	0.0191 (16)	0.0202 (16)
C10	0.0369 (17)	0.0317 (17)	0.0383 (19)	0.0159 (14)	0.0104 (14)	0.0119 (14)
C11	0.049 (2)	0.0405 (19)	0.045 (2)	0.0224 (16)	0.0168 (16)	0.0182 (16)
C12	0.054 (2)	0.052 (2)	0.0398 (19)	0.0374 (18)	0.0197 (16)	0.0224 (16)
C13	0.0432 (19)	0.053 (2)	0.051 (2)	0.0326 (17)	0.0251 (17)	0.0278 (18)
C14	0.054 (2)	0.071 (3)	0.068 (3)	0.041 (2)	0.032 (2)	0.048 (2)
C15	0.059 (2)	0.056 (3)	0.096 (3)	0.031 (2)	0.038 (2)	0.051 (3)
C16	0.045 (2)	0.050 (2)	0.081 (3)	0.0234 (18)	0.029 (2)	0.031 (2)
C17	0.046 (2)	0.053 (2)	0.051 (2)	0.0275 (18)	0.0185 (17)	0.0241 (19)
C18	0.049 (2)	0.046 (2)	0.054 (2)	0.0258 (17)	0.0237 (18)	0.0279 (18)
C19	0.074 (3)	0.054 (3)	0.084 (3)	0.024 (2)	0.013 (3)	0.009 (3)
C20	0.0368 (18)	0.0401 (18)	0.0383 (19)	0.0177 (15)	0.0099 (15)	0.0089 (15)
C21	0.049 (2)	0.057 (2)	0.046 (2)	0.0284 (18)	0.0134 (17)	0.0135 (18)
C22	0.046 (2)	0.066 (3)	0.059 (2)	0.0348 (19)	0.0120 (19)	0.012 (2)
C23	0.042 (2)	0.057 (2)	0.059 (2)	0.0179 (18)	0.0243 (18)	0.015 (2)
C24	0.045 (2)	0.0404 (19)	0.054 (2)	0.0158 (16)	0.0194 (17)	0.0161 (17)
C25	0.087 (3)	0.049 (2)	0.079 (3)	0.011 (2)	0.045 (3)	0.018 (2)
C26	0.046 (2)	0.051 (3)	0.097 (4)	0.010 (2)	0.020 (2)	−0.005 (2)
C27	0.076 (3)	0.055 (3)	0.060 (3)	0.019 (2)	−0.007 (2)	0.005 (2)
C28	0.087 (3)	0.057 (3)	0.055 (3)	0.020 (2)	0.028 (2)	0.007 (2)
C29	0.082 (3)	0.042 (2)	0.084 (3)	0.025 (2)	0.040 (3)	0.014 (2)

S2—C8	1.714 (3)	C10—C11	1.488 (4)
S2—C9	1.721 (3)	C11—C12	1.518 (4)
Fe—C28	2.013 (4)	C11—H11A	0.9700
Fe—C27	2.018 (4)	C11—H11B	0.9700
Fe—C20	2.019 (3)	C12—C13	1.505 (5)
Fe—C24	2.020 (3)	C12—H12	0.9800
Fe—C21	2.021 (4)	C13—C14	1.381 (4)
Fe—C29	2.027 (4)	C13—C18	1.392 (4)
Fe—C25	2.028 (4)	C14—C15	1.399 (5)
Fe—C26	2.031 (4)	C14—H14	0.9300
Fe—C22	2.031 (4)	C15—C16	1.337 (5)
Fe—C23	2.031 (4)	C15—H15	0.9300
O1—C16	1.376 (5)	C16—C17	1.367 (5)
O1—C19	1.392 (5)	C17—C18	1.344 (5)
O2—C17	1.359 (4)	C18—H18	0.9300
O2—C19	1.413 (5)	C19—H19A	0.9700
N2—C9	1.345 (4)	C19—H19B	0.9700
N2—N3	1.393 (3)	C20—C21	1.414 (5)
N2—C12	1.478 (4)	C20—C24	1.418 (4)
N3—C10	1.281 (4)	C21—C22	1.417 (5)
N7—C9	1.294 (4)	C21—H21	0.9800
N7—C7	1.388 (4)	C22—C23	1.405 (5)
C1—C2	1.369 (4)	C22—H22	0.9800
C1—C6	1.380 (4)	C23—C24	1.393 (5)
C1—H1	0.9300	C23—H23	0.9800
C2—C3	1.366 (5)	C24—H24	0.9800
C2—H2	0.9300	C25—C26	1.385 (6)
C3—C4	1.365 (5)	C25—C29	1.402 (5)
C3—H3	0.9300	C25—H25	0.9800
C4—C5	1.369 (5)	C26—C27	1.390 (6)
C4—H4	0.9300	C26—H26	0.9800
C5—C6	1.374 (4)	C27—C28	1.389 (6)
C5—H5	0.9300	C27—H27	0.9800
C6—C7	1.471 (4)	C28—C29	1.385 (6)
C7—C8	1.337 (4)	C28—H28	0.9800
C8—H8	0.9300	C29—H29	0.9800
C10—C20	1.443 (4)
C8—S2—C9	88.06 (16)	N2—C12—C11	100.6 (2)
C28—Fe—C27	40.31 (17)	C13—C12—C11	112.1 (3)
C28—Fe—C20	156.29 (17)	N2—C12—H12	110.4
C27—Fe—C20	121.27 (17)	C13—C12—H12	110.4
C28—Fe—C24	120.58 (17)	C11—C12—H12	110.4
C27—Fe—C24	107.07 (17)	C14—C13—C18	119.1 (3)
C20—Fe—C24	41.11 (13)	C14—C13—C12	123.0 (3)
C28—Fe—C21	161.29 (17)	C18—C13—C12	117.6 (3)
C27—Fe—C21	157.07 (18)	C13—C14—C15	121.6 (3)
C20—Fe—C21	40.97 (13)	C13—C14—H14	119.2
C24—Fe—C21	69.01 (15)	C15—C14—H14	119.2
C28—Fe—C29	40.11 (17)	C16—C15—C14	116.9 (3)
C27—Fe—C29	67.72 (19)	C16—C15—H15	121.5
C20—Fe—C29	162.05 (16)	C14—C15—H15	121.5
C24—Fe—C29	155.74 (16)	C15—C16—C17	122.2 (4)
C21—Fe—C29	125.12 (18)	C15—C16—O1	128.3 (4)
C28—Fe—C25	67.40 (18)	C17—C16—O1	109.5 (4)
C27—Fe—C25	67.3 (2)	C18—C17—O2	128.8 (3)
C20—Fe—C25	125.29 (16)	C18—C17—C16	122.0 (4)
C24—Fe—C25	161.49 (17)	O2—C17—C16	109.2 (3)
C21—Fe—C25	108.88 (18)	C17—C18—C13	118.2 (3)
C29—Fe—C25	40.46 (16)	C17—C18—H18	120.9
C28—Fe—C26	67.56 (18)	C13—C18—H18	120.9
C27—Fe—C26	40.16 (18)	O1—C19—O2	108.4 (3)
C20—Fe—C26	108.16 (15)	O1—C19—H19A	110.0
C24—Fe—C26	124.54 (17)	O2—C19—H19A	110.0
C21—Fe—C26	122.27 (18)	O1—C19—H19B	110.0
C29—Fe—C26	67.75 (18)	O2—C19—H19B	110.0
C25—Fe—C26	39.90 (18)	H19A—C19—H19B	108.4
C28—Fe—C22	124.29 (17)	C21—C20—C24	107.9 (3)
C27—Fe—C22	160.44 (19)	C21—C20—C10	127.3 (3)
C20—Fe—C22	68.64 (14)	C24—C20—C10	124.7 (3)
C24—Fe—C22	68.35 (15)	C21—C20—Fe	69.59 (19)
C21—Fe—C22	40.95 (13)	C24—C20—Fe	69.48 (18)
C29—Fe—C22	108.17 (17)	C10—C20—Fe	122.9 (2)
C25—Fe—C22	122.91 (19)	C20—C21—C22	107.5 (3)
C26—Fe—C22	157.9 (2)	C20—C21—Fe	69.4 (2)
C28—Fe—C23	107.49 (17)	C22—C21—Fe	69.9 (2)
C27—Fe—C23	123.92 (19)	C20—C21—H21	126.2
C20—Fe—C23	68.31 (14)	C22—C21—H21	126.2
C24—Fe—C23	40.24 (13)	Fe—C21—H21	126.2
C21—Fe—C23	68.53 (15)	C23—C22—C21	107.9 (3)
C29—Fe—C23	121.52 (16)	C23—C22—Fe	69.8 (2)
C25—Fe—C23	157.59 (18)	C21—C22—Fe	69.2 (2)
C26—Fe—C23	160.5 (2)	C23—C22—H22	126.1
C22—Fe—C23	40.48 (15)	C21—C22—H22	126.1
C16—O1—C19	104.9 (3)	Fe—C22—H22	126.1
C17—O2—C19	105.1 (3)	C24—C23—C22	108.8 (3)
C9—N2—N3	119.2 (3)	C24—C23—Fe	69.4 (2)
C9—N2—C12	125.6 (3)	C22—C23—Fe	69.8 (2)
N3—N2—C12	111.6 (2)	C24—C23—H23	125.6
C10—N3—N2	107.5 (2)	C22—C23—H23	125.6
C9—N7—C7	109.6 (3)	Fe—C23—H23	125.6
C2—C1—C6	120.9 (3)	C23—C24—C20	108.0 (3)
C2—C1—H1	119.6	C23—C24—Fe	70.3 (2)
C6—C1—H1	119.6	C20—C24—Fe	69.41 (18)
C3—C2—C1	119.9 (3)	C23—C24—H24	126.0
C3—C2—H2	120.1	C20—C24—H24	126.0
C1—C2—H2	120.1	Fe—C24—H24	126.0
C4—C3—C2	120.1 (3)	C26—C25—C29	108.5 (4)
C4—C3—H3	120.0	C26—C25—Fe	70.1 (2)
C2—C3—H3	120.0	C29—C25—Fe	69.7 (2)
C3—C4—C5	119.9 (3)	C26—C25—H25	125.8
C3—C4—H4	120.1	C29—C25—H25	125.8
C5—C4—H4	120.1	Fe—C25—H25	125.8
C4—C5—C6	121.0 (3)	C25—C26—C27	107.8 (4)
C4—C5—H5	119.5	C25—C26—Fe	70.0 (2)
C6—C5—H5	119.5	C27—C26—Fe	69.4 (2)
C5—C6—C1	118.2 (3)	C25—C26—H26	126.1
C5—C6—C7	121.7 (3)	C27—C26—H26	126.1
C1—C6—C7	120.1 (3)	Fe—C26—H26	126.1
C8—C7—N7	115.0 (3)	C28—C27—C26	108.0 (4)
C8—C7—C6	125.0 (3)	C28—C27—Fe	69.6 (3)
N7—C7—C6	120.0 (3)	C26—C27—Fe	70.4 (3)
C7—C8—S2	111.2 (3)	C28—C27—H27	126.0
C7—C8—H8	124.4	C26—C27—H27	126.0
S2—C8—H8	124.4	Fe—C27—H27	126.0
N7—C9—N2	124.1 (3)	C29—C28—C27	108.7 (4)
N7—C9—S2	116.1 (2)	C29—C28—Fe	70.5 (2)
N2—C9—S2	119.8 (2)	C27—C28—Fe	70.1 (2)
N3—C10—C20	122.6 (3)	C29—C28—H28	125.7
N3—C10—C11	113.8 (3)	C27—C28—H28	125.7
C20—C10—C11	123.6 (3)	Fe—C28—H28	125.7
C10—C11—C12	102.0 (3)	C28—C29—C25	107.1 (4)
C10—C11—H11A	111.4	C28—C29—Fe	69.4 (2)
C12—C11—H11A	111.4	C25—C29—Fe	69.8 (2)
C10—C11—H11B	111.4	C28—C29—H29	126.5
C12—C11—H11B	111.4	C25—C29—H29	126.5
H11A—C11—H11B	109.2	Fe—C29—H29	126.5
N2—C12—C13	112.5 (3)

Cg1, Cg2, Cg3 and Cg4 are the centroids of the C13–C18, C25–C29, C1–C6 and C20–C24 rings, respectively.

D—H···A	D—H	H···A	D···A	D—H···A
C15—H15···N3i	0.93	2.49	3.402 (6)	168
C28—H28···O2ii	0.98	2.43	3.337 (6)	153
C22—H22···Cg1iii	0.98	2.97	3.709 (5)	133
C26—H26···Cg1	0.98	2.90	3.844 (5)	163
C5—H5···Cg2iv	0.93	2.91	3.658 (5)	138
C8—H8···Cg3v	0.93	2.98	3.590 (4)	125
C11—H11A···Cg4vi	0.97	2.85	3.670 (4)	142

Table 1

Hydrogen-bond geometry (Å, °)

Cg1, Cg2, Cg3 and Cg4 are the centroids of the C13–C18, C25–C29, C1–C6 and C20–C24 rings, respectively.

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C15—H15⋯N3i	0.93	2.49	3.402 (6)	168
C28—H28⋯O2ii	0.98	2.43	3.337 (6)	153
C22—H22⋯Cg1iii	0.98	2.97	3.709 (5)	133
C26—H26⋯Cg1	0.98	2.90	3.844 (5)	163
C5—H5⋯Cg2iv	0.93	2.91	3.658 (5)	138
C8—H8⋯Cg3v	0.93	2.98	3.590 (4)	125
C11—H11A⋯Cg4vi	0.97	2.85	3.670 (4)	142

Symmetry codes: (i) ; (ii) ; (iii) ; (iv) ; (v) ; (vi) .