Crystal structure of N,N,N-tris-[(1,3-benzo-thia-zol-2-yl)meth-yl]amine.

The title compound, C24H18N4S3, exhibits three near planar benzo-thia-zole systems in a pseudo-C 3 conformation. The dihedral angles between the planes of the benzo-thia-zole groups range from 112.56 (4) to 124.68 (4)° In the crystal, mol-ecules are connected to each other through three short C-H⋯N contacts, forming an infinite chain along [100]. The molecules are also linked by π-π interactions with each of the three five-membered thiazole rings. [inter-centroid distance range: 3.614 (1)-4.074 (1) Å, inter-planar distance range: 3.4806 (17)-3.6902 (15) Å, slippage range: 0.759 (3)-1.887 (3) Å].

Related literature

For synthesis of the title compound and a structure of the ligand bound to copper, see: Thompson et al. (1980 ▸). For a related organic structure, see: Zhang et al. (2009 ▸). For other related structures, see; Bautista & Thompson (1980 ▸); Pandey & Mathur (1995 ▸). For a study of its use as a ligand in azide–alkyne cyclo­additions, see: Rodionov, Presolski, Gardinier et al. (2007 ▸); Rodionov, Presolski, Diaz et al. (2007 ▸).

Experimental

Crystal data

C24H18N4S3

M = 495.66

Triclinic,

a = 6.6530 (3) Å

b = 14.3098 (6) Å

c = 14.5822 (7) Å

α = 61.471 (1)°

β = 88.474 (2)°

γ = 79.138 (1)°

V = 1194.61 (9) Å3

Z = 2

Mo Kα radiation

μ = 0.34 mm−1

T = 100 K

0.15 × 0.12 × 0.10 mm

Data collection

Bruker APEXII CCD diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2005 ▸) T min = 0.951, T max = 0.967

4691 measured reflections

4691 independent reflections

3767 reflections with I > 2σ(I)

R int = 0.000

Refinement

R[F 2 > 2σ(F 2)] = 0.038

wR(F 2) = 0.110

S = 1.08

4691 reflections

280 parameters

H-atom parameters constrained

Δρmax = 0.28 e Å−3

Δρmin = −0.29 e Å−3

Data collection: APEX2 (Bruker, 2005 ▸); cell refinement: SAINT (Bruker, 2005 ▸); data reduction: SAINT; 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: publCIF (Westrip, 2010 ▸) and PLATON (Spek, 2009 ▸).

Crystal structure: contains datablock(s) I, New_Global_Publ_Block. DOI: 10.1107/S2056989015017417/ff2141sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S2056989015017417/ff2141Isup2.hkl

Supporting information file. DOI: 10.1107/S2056989015017417/ff2141Isup3.txt

Click here for additional data file.

Supporting information file. DOI: 10.1107/S2056989015017417/ff2141Isup4.cml

Click here for additional data file.

. DOI: 10.1107/S2056989015017417/ff2141fig1.tif

Mol­ecular structure of the title compound, showing the atom labelling scheme. Displacement ellipsoids are drawn at the 50% probability level. H atoms are presented as spheres of arbitrary radius.

Click here for additional data file.

. DOI: 10.1107/S2056989015017417/ff2141fig2.tif

Mol­ecular packing of the title compound.

CCDC reference: 1425576

Additional supporting information: crystallographic information; 3D view; checkCIF report

C24H18N4S3	Z = 2
Mr = 495.66	F(000) = 518
Triclinic, P1	Dx = 1.378 Mg m−3
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 6.6530 (3) Å	Cell parameters from 6510 reflections
b = 14.3098 (6) Å	θ = 3.1–25.7°
c = 14.5822 (7) Å	µ = 0.34 mm−1
α = 61.471 (1)°	T = 100 K
β = 88.474 (2)°	Block, yellow
γ = 79.138 (1)°	0.15 × 0.12 × 0.10 mm
V = 1194.61 (9) Å3

Bruker APEXII CCD diffractometer	4691 independent reflections
Radiation source: fine-focus ROTATING ANODE	3767 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.0000
φ and ω scans	θmax = 26.0°, θmin = 1.6°
Absorption correction: multi-scan (SADABS; Bruker, 2005)	h = −8→8
Tmin = 0.951, Tmax = 0.967	k = −15→17
4691 measured reflections	l = 0→17

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)] = 0.038	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.110	H-atom parameters constrained
S = 1.08	w = 1/[σ2(Fo2) + (0.0612P)2 + 0.0926P] where P = (Fo2 + 2Fc2)/3
4691 reflections	(Δ/σ)max < 0.001
280 parameters	Δρmax = 0.28 e Å−3
0 restraints	Δρmin = −0.29 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
S1	0.40279 (7)	0.15702 (4)	0.47208 (4)	0.04313 (15)
S2	0.27604 (8)	0.38911 (4)	0.15881 (4)	0.04461 (16)
S3	0.25502 (7)	0.44886 (4)	0.38876 (5)	0.04767 (16)
N1	0.1195 (2)	0.05355 (12)	0.57200 (13)	0.0416 (4)
N2	−0.0211 (2)	0.34050 (12)	0.08966 (12)	0.0405 (4)
N3	−0.1239 (2)	0.54789 (12)	0.36542 (12)	0.0382 (4)
N4	−0.0043 (2)	0.30973 (12)	0.34526 (12)	0.0368 (4)
C1	0.0012 (3)	0.19336 (15)	0.39103 (15)	0.0418 (5)
H1B	0.0358	0.1702	0.3375	0.050*
H1A	−0.1361	0.1784	0.4139	0.050*
C2	0.1562 (3)	0.13010 (14)	0.48240 (15)	0.0384 (4)
C3	0.4652 (3)	0.05555 (14)	0.60010 (15)	0.0387 (4)
C4	0.6507 (3)	0.01905 (15)	0.66060 (18)	0.0483 (5)
H4A	0.7686	0.0480	0.6318	0.058*
C5	0.6574 (3)	−0.06029 (16)	0.76342 (18)	0.0558 (6)
H5A	0.7813	−0.0853	0.8064	0.067*
C6	0.4877 (4)	−0.10437 (17)	0.8055 (2)	0.0628 (6)
H6A	0.4962	−0.1581	0.8770	0.075*
C7	0.3052 (3)	−0.07124 (16)	0.74462 (18)	0.0570 (6)
H7A	0.1903	−0.1035	0.7731	0.068*
C8	0.2940 (3)	0.00976 (13)	0.64160 (16)	0.0403 (4)
C9	−0.1080 (3)	0.37025 (16)	0.23985 (15)	0.0424 (5)
H9A	−0.1536	0.4475	0.2214	0.051*
H9B	−0.2311	0.3412	0.2388	0.051*
C10	0.0308 (3)	0.36203 (14)	0.16109 (14)	0.0374 (4)
C11	0.3140 (3)	0.37193 (14)	0.04962 (14)	0.0375 (4)
C12	0.4860 (3)	0.37765 (15)	−0.00699 (15)	0.0440 (5)
H12A	0.6035	0.3968	0.0099	0.053*
C13	0.4821 (3)	0.35475 (16)	−0.08855 (15)	0.0473 (5)
H13A	0.5984	0.3582	−0.1284	0.057*
C14	0.3113 (3)	0.32676 (17)	−0.11319 (16)	0.0521 (5)
H14A	0.3129	0.3104	−0.1692	0.063*
C15	0.1381 (3)	0.32219 (17)	−0.05775 (16)	0.0501 (5)
H15A	0.0205	0.3039	−0.0758	0.060*
C16	0.1393 (3)	0.34469 (14)	0.02442 (14)	0.0377 (4)
C17	−0.0894 (3)	0.35415 (15)	0.41340 (16)	0.0411 (4)
H17A	−0.0500	0.2993	0.4875	0.049*
H17B	−0.2410	0.3719	0.4032	0.049*
C18	−0.0096 (3)	0.45492 (15)	0.38820 (14)	0.0375 (4)
C19	0.2093 (3)	0.58523 (15)	0.35501 (14)	0.0385 (4)
C20	0.3495 (3)	0.65143 (16)	0.33751 (17)	0.0477 (5)
H20A	0.4930	0.6233	0.3468	0.057*
C21	0.2730 (4)	0.75976 (17)	0.30610 (18)	0.0531 (5)
H21A	0.3657	0.8073	0.2922	0.064*
C22	0.0642 (3)	0.80027 (16)	0.29458 (17)	0.0521 (5)
H22A	0.0159	0.8752	0.2726	0.062*
C23	−0.0763 (3)	0.73355 (16)	0.31451 (17)	0.0486 (5)
H23A	−0.2196	0.7617	0.3073	0.058*
C24	−0.0023 (3)	0.62444 (14)	0.34531 (14)	0.0364 (4)

	U11	U22	U33	U12	U13	U23
S1	0.0398 (3)	0.0435 (3)	0.0487 (3)	−0.0190 (2)	0.0104 (2)	−0.0209 (2)
S2	0.0367 (3)	0.0614 (3)	0.0469 (3)	−0.0167 (2)	0.0027 (2)	−0.0324 (3)
S3	0.0343 (3)	0.0435 (3)	0.0722 (4)	−0.0075 (2)	0.0131 (2)	−0.0339 (3)
N1	0.0365 (9)	0.0334 (8)	0.0527 (10)	−0.0113 (7)	0.0097 (8)	−0.0179 (8)
N2	0.0331 (8)	0.0457 (9)	0.0415 (9)	−0.0078 (7)	−0.0041 (7)	−0.0197 (8)
N3	0.0354 (8)	0.0461 (9)	0.0381 (9)	−0.0046 (7)	0.0009 (7)	−0.0253 (7)
N4	0.0352 (8)	0.0386 (8)	0.0390 (9)	−0.0090 (7)	0.0041 (7)	−0.0201 (7)
C1	0.0392 (11)	0.0432 (10)	0.0479 (12)	−0.0160 (8)	0.0061 (9)	−0.0232 (9)
C2	0.0373 (10)	0.0346 (9)	0.0504 (12)	−0.0123 (8)	0.0103 (9)	−0.0247 (9)
C3	0.0369 (10)	0.0308 (9)	0.0528 (12)	−0.0070 (8)	0.0085 (9)	−0.0237 (9)
C4	0.0384 (11)	0.0405 (10)	0.0672 (15)	−0.0057 (9)	0.0051 (10)	−0.0277 (11)
C5	0.0469 (13)	0.0415 (11)	0.0648 (15)	0.0036 (9)	−0.0063 (11)	−0.0183 (11)
C6	0.0592 (15)	0.0426 (12)	0.0606 (15)	0.0021 (11)	0.0007 (12)	−0.0085 (11)
C7	0.0500 (13)	0.0374 (11)	0.0658 (15)	−0.0093 (9)	0.0130 (11)	−0.0110 (11)
C8	0.0378 (10)	0.0288 (9)	0.0525 (12)	−0.0066 (8)	0.0088 (9)	−0.0184 (9)
C9	0.0331 (10)	0.0485 (11)	0.0446 (11)	−0.0055 (8)	−0.0005 (8)	−0.0225 (9)
C10	0.0324 (10)	0.0362 (9)	0.0390 (11)	−0.0056 (8)	−0.0043 (8)	−0.0146 (8)
C11	0.0368 (10)	0.0353 (9)	0.0334 (10)	−0.0069 (8)	−0.0041 (8)	−0.0109 (8)
C12	0.0406 (11)	0.0473 (11)	0.0415 (11)	−0.0137 (9)	0.0020 (9)	−0.0176 (9)
C13	0.0490 (12)	0.0500 (12)	0.0358 (11)	−0.0078 (9)	0.0037 (9)	−0.0158 (9)
C14	0.0560 (14)	0.0618 (13)	0.0373 (11)	−0.0071 (11)	−0.0024 (10)	−0.0244 (10)
C15	0.0468 (12)	0.0616 (13)	0.0448 (12)	−0.0143 (10)	−0.0070 (10)	−0.0263 (10)
C16	0.0376 (10)	0.0362 (9)	0.0334 (10)	−0.0043 (8)	−0.0069 (8)	−0.0126 (8)
C17	0.0345 (10)	0.0463 (11)	0.0481 (12)	−0.0117 (8)	0.0106 (9)	−0.0261 (9)
C18	0.0350 (10)	0.0444 (10)	0.0371 (10)	−0.0087 (8)	0.0070 (8)	−0.0228 (9)
C19	0.0393 (11)	0.0428 (10)	0.0401 (11)	−0.0071 (8)	0.0080 (8)	−0.0258 (9)
C20	0.0420 (11)	0.0521 (12)	0.0616 (13)	−0.0119 (9)	0.0134 (10)	−0.0368 (11)
C21	0.0573 (14)	0.0525 (12)	0.0647 (15)	−0.0193 (10)	0.0162 (11)	−0.0379 (11)
C22	0.0600 (14)	0.0419 (11)	0.0588 (14)	−0.0065 (10)	0.0019 (11)	−0.0290 (10)
C23	0.0453 (12)	0.0484 (11)	0.0535 (13)	0.0009 (9)	−0.0042 (10)	−0.0290 (10)
C24	0.0387 (10)	0.0426 (10)	0.0330 (10)	−0.0058 (8)	0.0010 (8)	−0.0230 (8)

S1—C3	1.729 (2)	C7—H7A	0.9500
S1—C2	1.7415 (18)	C9—C10	1.489 (3)
S2—C11	1.729 (2)	C9—H9A	0.9900
S2—C10	1.7423 (18)	C9—H9B	0.9900
S3—C19	1.7349 (18)	C11—C12	1.385 (3)
S3—C18	1.7460 (18)	C11—C16	1.403 (3)
N1—C2	1.297 (2)	C12—C13	1.378 (3)
N1—C8	1.397 (2)	C12—H12A	0.9500
N2—C10	1.290 (2)	C13—C14	1.383 (3)
N2—C16	1.401 (2)	C13—H13A	0.9500
N3—C18	1.292 (2)	C14—C15	1.384 (3)
N3—C24	1.398 (2)	C14—H14A	0.9500
N4—C1	1.462 (2)	C15—C16	1.382 (3)
N4—C9	1.466 (2)	C15—H15A	0.9500
N4—C17	1.466 (2)	C17—C18	1.506 (2)
C1—C2	1.493 (3)	C17—H17A	0.9900
C1—H1B	0.9900	C17—H17B	0.9900
C1—H1A	0.9900	C19—C20	1.386 (3)
C3—C4	1.396 (3)	C19—C24	1.398 (3)
C3—C8	1.399 (3)	C20—C21	1.381 (3)
C4—C5	1.377 (3)	C20—H20A	0.9500
C4—H4A	0.9500	C21—C22	1.382 (3)
C5—C6	1.382 (3)	C21—H21A	0.9500
C5—H5A	0.9500	C22—C23	1.388 (3)
C6—C7	1.388 (3)	C22—H22A	0.9500
C6—H6A	0.9500	C23—C24	1.391 (3)
C7—C8	1.384 (3)	C23—H23A	0.9500
C3—S1—C2	89.03 (9)	C12—C11—C16	121.21 (18)
C11—S2—C10	89.09 (9)	C12—C11—S2	129.24 (15)
C19—S3—C18	89.02 (9)	C16—C11—S2	109.49 (14)
C2—N1—C8	110.35 (15)	C13—C12—C11	118.16 (19)
C10—N2—C16	110.28 (15)	C13—C12—H12A	120.9
C18—N3—C24	110.23 (15)	C11—C12—H12A	120.9
C1—N4—C9	111.51 (14)	C12—C13—C14	120.96 (19)
C1—N4—C17	112.81 (14)	C12—C13—H13A	119.5
C9—N4—C17	112.20 (14)	C14—C13—H13A	119.5
N4—C1—C2	110.82 (14)	C13—C14—C15	121.1 (2)
N4—C1—H1B	109.5	C13—C14—H14A	119.4
C2—C1—H1B	109.5	C15—C14—H14A	119.4
N4—C1—H1A	109.5	C16—C15—C14	118.71 (19)
C2—C1—H1A	109.5	C16—C15—H15A	120.6
H1B—C1—H1A	108.1	C14—C15—H15A	120.6
N1—C2—C1	123.72 (17)	C15—C16—N2	125.52 (18)
N1—C2—S1	116.22 (15)	C15—C16—C11	119.80 (18)
C1—C2—S1	120.06 (13)	N2—C16—C11	114.66 (16)
C4—C3—C8	120.91 (18)	N4—C17—C18	109.94 (14)
C4—C3—S1	129.40 (15)	N4—C17—H17A	109.7
C8—C3—S1	109.69 (14)	C18—C17—H17A	109.7
C5—C4—C3	117.91 (19)	N4—C17—H17B	109.7
C5—C4—H4A	121.0	C18—C17—H17B	109.7
C3—C4—H4A	121.0	H17A—C17—H17B	108.2
C4—C5—C6	121.4 (2)	N3—C18—C17	124.56 (16)
C4—C5—H5A	119.3	N3—C18—S3	116.31 (14)
C6—C5—H5A	119.3	C17—C18—S3	119.13 (14)
C5—C6—C7	120.9 (2)	C20—C19—C24	121.92 (17)
C5—C6—H6A	119.6	C20—C19—S3	128.84 (15)
C7—C6—H6A	119.6	C24—C19—S3	109.24 (13)
C8—C7—C6	118.6 (2)	C21—C20—C19	117.64 (19)
C8—C7—H7A	120.7	C21—C20—H20A	121.2
C6—C7—H7A	120.7	C19—C20—H20A	121.2
C7—C8—N1	125.12 (18)	C20—C21—C22	121.2 (2)
C7—C8—C3	120.18 (19)	C20—C21—H21A	119.4
N1—C8—C3	114.70 (17)	C22—C21—H21A	119.4
N4—C9—C10	111.13 (15)	C21—C22—C23	121.23 (19)
N4—C9—H9A	109.4	C21—C22—H22A	119.4
C10—C9—H9A	109.4	C23—C22—H22A	119.4
N4—C9—H9B	109.4	C22—C23—C24	118.42 (19)
C10—C9—H9B	109.4	C22—C23—H23A	120.8
H9A—C9—H9B	108.0	C24—C23—H23A	120.8
N2—C10—C9	124.19 (17)	C23—C24—N3	125.21 (17)
N2—C10—S2	116.46 (15)	C23—C24—C19	119.57 (17)
C9—C10—S2	119.28 (14)	N3—C24—C19	115.20 (16)
C9—N4—C1—C2	163.44 (15)	C11—C12—C13—C14	0.0 (3)
C17—N4—C1—C2	−69.23 (19)	C12—C13—C14—C15	0.8 (3)
C8—N1—C2—C1	−179.97 (16)	C13—C14—C15—C16	−0.9 (3)
C8—N1—C2—S1	0.3 (2)	C14—C15—C16—N2	−178.09 (17)
N4—C1—C2—N1	132.22 (18)	C14—C15—C16—C11	0.3 (3)
N4—C1—C2—S1	−48.1 (2)	C10—N2—C16—C15	177.63 (18)
C3—S1—C2—N1	0.28 (15)	C10—N2—C16—C11	−0.8 (2)
C3—S1—C2—C1	−179.47 (15)	C12—C11—C16—C15	0.5 (3)
C2—S1—C3—C4	179.89 (18)	S2—C11—C16—C15	−177.11 (15)
C2—S1—C3—C8	−0.75 (14)	C12—C11—C16—N2	179.05 (16)
C8—C3—C4—C5	−2.5 (3)	S2—C11—C16—N2	1.42 (19)
S1—C3—C4—C5	176.78 (16)	C1—N4—C17—C18	155.22 (15)
C3—C4—C5—C6	1.2 (3)	C9—N4—C17—C18	−77.82 (19)
C4—C5—C6—C7	1.1 (4)	C24—N3—C18—C17	−179.50 (16)
C5—C6—C7—C8	−2.2 (3)	C24—N3—C18—S3	0.4 (2)
C6—C7—C8—N1	−178.05 (19)	N4—C17—C18—N3	126.01 (19)
C6—C7—C8—C3	0.9 (3)	N4—C17—C18—S3	−53.8 (2)
C2—N1—C8—C7	178.12 (19)	C19—S3—C18—N3	0.05 (15)
C2—N1—C8—C3	−0.9 (2)	C19—S3—C18—C17	179.91 (15)
C4—C3—C8—C7	1.4 (3)	C18—S3—C19—C20	−179.60 (19)
S1—C3—C8—C7	−177.98 (16)	C18—S3—C19—C24	−0.43 (14)
C4—C3—C8—N1	−179.48 (16)	C24—C19—C20—C21	−2.3 (3)
S1—C3—C8—N1	1.1 (2)	S3—C19—C20—C21	176.77 (16)
C1—N4—C9—C10	−79.28 (18)	C19—C20—C21—C22	1.3 (3)
C17—N4—C9—C10	153.06 (15)	C20—C21—C22—C23	0.2 (3)
C16—N2—C10—C9	176.60 (16)	C21—C22—C23—C24	−0.8 (3)
C16—N2—C10—S2	−0.2 (2)	C22—C23—C24—N3	−178.19 (18)
N4—C9—C10—N2	133.35 (18)	C22—C23—C24—C19	−0.2 (3)
N4—C9—C10—S2	−49.92 (19)	C18—N3—C24—C23	177.37 (18)
C11—S2—C10—N2	0.87 (15)	C18—N3—C24—C19	−0.7 (2)
C11—S2—C10—C9	−176.10 (15)	C20—C19—C24—C23	1.8 (3)
C10—S2—C11—C12	−178.60 (18)	S3—C19—C24—C23	−177.46 (14)
C10—S2—C11—C16	−1.23 (13)	C20—C19—C24—N3	179.98 (17)
C16—C11—C12—C13	−0.6 (3)	S3—C19—C24—N3	0.7 (2)
S2—C11—C12—C13	176.48 (14)

D—H···A	D—H	H···A	D···A	D—H···A
C4—H4A···N1i	0.95	2.47	3.376 (3)	159
C12—H12A···N2i	0.95	2.60	3.449 (2)	150
C20—H20A···N3i	0.95	2.54	3.490 (3)	178

Table 1

Hydrogen-bond geometry (, )

DHA	DH	HA	D A	DHA
C4H4AN1i	0.95	2.47	3.376(3)	159
C12H12AN2i	0.95	2.60	3.449(2)	150
C20H20AN3i	0.95	2.54	3.490(3)	178

Symmetry code: (i) .