Crystal structure of 3,5-bis-(4-chloro-phen-yl)-1-propyl-1,3,5-tri-aza-cyclo-hexane.

In the title mol-ecule, C18H21Cl2N3, the tri-aza-cyclo-hexane ring adopts a chair conformation with both 4-chloro-phenyl substituents in axial positions and the propyl group in an equatorial site. The dihedral angle between the planes of the benzene rings is 49.5 (1)°. In the crystal, mol-ecules are arranged in a head-to-tail fashion, forming columns along [010], and pairs of weak C-H⋯π inter-actions form inversion dimers between columns.

Related literature

For conformations of 1,3,5-triaryl derivatives of 1,3,5-tri­aza­cyclo­hexane, see: Baker et al. (1978 ▶); Bouchemma et al. (1989 ▶, 1990 ▶); Bushweller (1995 ▶); Kleinpeter et al. (2005 ▶); Duke et al. (1973 ▶); Gilardi et al. (2003 ▶); Giumanini et al. (1985 ▶); Latreche et al. (2006 ▶); Mloston et al. (2006 ▶); Freeman et al. (2005 ▶); Wiberg et al. (1999 ▶).

Experimental

Crystal data

C18H21Cl2N3

M = 350.28

Triclinic,

a = 6.0785 (3) Å

b = 10.3190 (6) Å

c = 14.4360 (8) Å

α = 91.570 (3)°

β = 91.946 (2)°

γ = 99.055 (3)°

V = 893.19 (8) Å3

Z = 2

Mo Kα radiation

μ = 0.37 mm−1

T = 295 K

0.22 × 0.13 × 0.07 mm

Data collection

Nonius KappaCCD diffractometer

Absorption correction: multi-scan (Blessing, 1995 ▶) T min = 0.274, T max = 0.467

13643 measured reflections

3448 independent reflections

2751 reflections with I > 2σ(I)

R int = 0.016

Refinement

R[F 2 > 2σ(F 2)] = 0.049

wR(F 2) = 0.142

S = 1.03

3448 reflections

209 parameters

H-atom parameters constrained

Δρmax = 0.45 e Å−3

Δρmin = −0.25 e Å−3

Data collection: COLLECT (Nonius, 1997 ▶); cell refinement: SCALEPACK (Otwinowski & Minor, 1997 ▶); data reduction: DENZO (Otwinowski & Minor, 1997 ▶) and SCALEPACK; program(s) used to solve structure: SIR2002 (Burla et al., 2005 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: ORTEP-3 for Windows (Farrugia, 2012 ▶) and DIAMOND (Brandenburg & Berndt, 2001 ▶); software used to prepare material for publication: WinGX (Farrugia, 2012 ▶).

Crystal structure: contains datablock(s) I. DOI: 10.1107/S1600536814019060/lh5723sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536814019060/lh5723Isup2.hkl

Click here for additional data file.

Supporting information file. DOI: 10.1107/S1600536814019060/lh5723Isup3.cml

Click here for additional data file.

. DOI: 10.1107/S1600536814019060/lh5723fig1.tif

The mol­ecular structure of the title compound with displacement ellipsoids drawn at the 50% probability level.

Click here for additional data file.

. DOI: 10.1107/S1600536814019060/lh5723fig2.tif

Part of the crystal structure of the title compound showing the ’head to tail’ arrangement of mol­ecules arranged in columns.

CCDC reference: 1020727

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

C18H21Cl2N3	Z = 2
Mr = 350.28	F(000) = 368
Triclinic, P1	Dx = 1.302 Mg m−3
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 6.0785 (3) Å	Cell parameters from 13346 reflections
b = 10.3190 (6) Å	θ = 1.5–27.3°
c = 14.4360 (8) Å	µ = 0.37 mm−1
α = 91.570 (3)°	T = 295 K
β = 91.946 (2)°	Prism, colourless
γ = 99.055 (3)°	0.22 × 0.13 × 0.07 mm
V = 893.19 (8) Å3

Nonius KappaCCD diffractometer	2751 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.016
ω and φ scans	θmax = 27.3°, θmin = 1.4°
Absorption correction: multi-scan (Blessing, 1995)	h = −7→7
Tmin = 0.274, Tmax = 0.467	k = −12→12
13643 measured reflections	l = −17→17
3448 independent reflections

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)] = 0.049	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.142	H-atom parameters constrained
S = 1.03	w = 1/[σ2(Fo2) + (0.0652P)2 + 0.413P] where P = (Fo2 + 2Fc2)/3
3448 reflections	(Δ/σ)max < 0.001
209 parameters	Δρmax = 0.45 e Å−3
0 restraints	Δρmin = −0.25 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
C1	−0.3001 (4)	0.4766 (3)	0.25020 (16)	0.0613 (6)
H1A	−0.3547	0.383	0.2459	0.074*
H1B	−0.4281	0.5221	0.2505	0.074*
C2	−0.0783 (4)	0.6456 (2)	0.34207 (17)	0.0633 (6)
H2A	0.0103	0.6653	0.3993	0.076*
H2B	−0.1997	0.6964	0.3432	0.076*
C3	−0.0772 (5)	0.6525 (2)	0.17830 (18)	0.0652 (6)
H3A	−0.1979	0.7039	0.1778	0.078*
H3B	0.013	0.6767	0.1254	0.078*
C4	0.1485 (6)	0.8253 (3)	0.2756 (2)	0.0847 (8)
H4A	0.0283	0.8751	0.2638	0.102*
H4B	0.2019	0.8438	0.3394	0.102*
C5	0.3281 (8)	0.8689 (4)	0.2147 (3)	0.1185 (14)
H5A	0.2688	0.865	0.1513	0.142*
H5B	0.4368	0.8096	0.2185	0.142*
C6	0.4450 (8)	1.0093 (4)	0.2390 (3)	0.1321 (17)
H6A	0.3366	1.0677	0.2395	0.198*
H6B	0.5531	1.0364	0.1935	0.198*
H6C	0.5184	1.0117	0.2991	0.198*
C11	−0.0360 (4)	0.4255 (2)	0.13332 (14)	0.0505 (5)
C12	0.1801 (4)	0.4642 (2)	0.10651 (16)	0.0556 (5)
H12	0.2467	0.5511	0.1166	0.067*
C13	0.2992 (4)	0.3762 (2)	0.06492 (16)	0.0590 (6)
H13	0.4436	0.4041	0.0465	0.071*
C14	0.2027 (4)	0.2473 (2)	0.05101 (16)	0.0585 (6)
C15	−0.0100 (4)	0.2056 (2)	0.07759 (19)	0.0691 (7)
H15	−0.0742	0.1181	0.0685	0.083*
C16	−0.1281 (4)	0.2940 (2)	0.11776 (19)	0.0666 (6)
H16	−0.2732	0.2653	0.135	0.08*
C21	−0.0324 (4)	0.4175 (2)	0.36755 (14)	0.0491 (5)
C22	−0.1257 (4)	0.2865 (2)	0.37598 (18)	0.0622 (6)
H22	−0.2735	0.2589	0.3566	0.075*
C23	−0.0036 (4)	0.1967 (2)	0.41250 (19)	0.0660 (6)
H23	−0.0682	0.1094	0.4173	0.079*
C24	0.2138 (4)	0.2375 (2)	0.44168 (16)	0.0583 (6)
C25	0.3124 (4)	0.3650 (2)	0.43325 (16)	0.0565 (5)
H25	0.4605	0.3913	0.4526	0.068*
C26	0.1900 (4)	0.4544 (2)	0.39570 (15)	0.0536 (5)
H26	0.2579	0.5408	0.3892	0.064*
N1	−0.1697 (3)	0.51418 (19)	0.16948 (13)	0.0578 (5)
N2	−0.1687 (3)	0.50789 (19)	0.33683 (13)	0.0561 (5)
N3	0.0600 (4)	0.68403 (18)	0.26379 (14)	0.0615 (5)
Cl1	0.34990 (13)	0.13680 (7)	−0.00400 (5)	0.0841 (3)
Cl2	0.36408 (14)	0.12627 (7)	0.49405 (6)	0.0865 (3)

	U11	U22	U33	U12	U13	U23
C1	0.0497 (13)	0.0749 (16)	0.0606 (14)	0.0138 (11)	0.0016 (10)	0.0033 (11)
C2	0.0733 (16)	0.0592 (14)	0.0614 (14)	0.0235 (12)	0.0035 (12)	−0.0017 (11)
C3	0.0750 (16)	0.0586 (14)	0.0659 (15)	0.0211 (12)	0.0029 (12)	0.0117 (11)
C4	0.108 (2)	0.0557 (15)	0.090 (2)	0.0095 (15)	0.0082 (18)	0.0044 (14)
C5	0.146 (4)	0.088 (2)	0.115 (3)	−0.010 (2)	0.040 (3)	−0.009 (2)
C6	0.173 (4)	0.088 (3)	0.115 (3)	−0.044 (3)	0.017 (3)	0.006 (2)
C11	0.0516 (12)	0.0559 (12)	0.0421 (10)	0.0039 (10)	−0.0054 (9)	0.0039 (9)
C12	0.0574 (13)	0.0499 (12)	0.0562 (12)	−0.0013 (10)	−0.0019 (10)	0.0039 (10)
C13	0.0545 (13)	0.0635 (14)	0.0572 (13)	0.0030 (11)	0.0037 (10)	0.0052 (11)
C14	0.0639 (14)	0.0586 (13)	0.0519 (12)	0.0084 (11)	−0.0040 (10)	−0.0039 (10)
C15	0.0691 (16)	0.0530 (14)	0.0799 (17)	−0.0045 (12)	−0.0021 (13)	−0.0076 (12)
C16	0.0536 (13)	0.0641 (15)	0.0778 (16)	−0.0036 (11)	0.0046 (12)	−0.0022 (12)
C21	0.0510 (12)	0.0533 (12)	0.0431 (11)	0.0077 (9)	0.0077 (9)	−0.0002 (9)
C22	0.0524 (13)	0.0587 (14)	0.0725 (15)	−0.0012 (11)	0.0051 (11)	0.0020 (11)
C23	0.0690 (16)	0.0492 (13)	0.0782 (16)	0.0015 (11)	0.0125 (13)	0.0071 (11)
C24	0.0664 (15)	0.0554 (13)	0.0564 (13)	0.0164 (11)	0.0126 (11)	0.0087 (10)
C25	0.0528 (12)	0.0610 (13)	0.0561 (13)	0.0102 (10)	0.0020 (10)	0.0024 (10)
C26	0.0562 (13)	0.0486 (12)	0.0541 (12)	0.0018 (10)	0.0059 (10)	0.0023 (9)
N1	0.0583 (11)	0.0619 (11)	0.0538 (11)	0.0113 (9)	−0.0016 (8)	0.0046 (9)
N2	0.0567 (11)	0.0603 (11)	0.0525 (10)	0.0130 (9)	0.0024 (8)	0.0000 (8)
N3	0.0734 (13)	0.0446 (10)	0.0665 (12)	0.0104 (9)	−0.0022 (10)	0.0023 (9)
Cl1	0.0883 (5)	0.0780 (5)	0.0872 (5)	0.0207 (4)	0.0049 (4)	−0.0199 (4)
Cl2	0.0940 (5)	0.0765 (5)	0.0981 (6)	0.0357 (4)	0.0131 (4)	0.0278 (4)

C1—N1	1.458 (3)	C11—C16	1.393 (3)
C1—N2	1.461 (3)	C11—N1	1.417 (3)
C1—H1A	0.97	C12—C13	1.384 (3)
C1—H1B	0.97	C12—H12	0.93
C2—N2	1.439 (3)	C13—C14	1.372 (3)
C2—N3	1.458 (3)	C13—H13	0.93
C2—H2A	0.97	C14—C15	1.368 (4)
C2—H2B	0.97	C14—Cl1	1.747 (2)
C3—N1	1.450 (3)	C15—C16	1.374 (4)
C3—N3	1.465 (3)	C15—H15	0.93
C3—H3A	0.97	C16—H16	0.93
C3—H3B	0.97	C21—C26	1.389 (3)
C4—C5	1.448 (5)	C21—C22	1.392 (3)
C4—N3	1.475 (3)	C21—N2	1.412 (3)
C4—H4A	0.97	C22—C23	1.380 (4)
C4—H4B	0.97	C22—H22	0.93
C5—C6	1.536 (4)	C23—C24	1.371 (4)
C5—H5A	0.97	C23—H23	0.93
C5—H5B	0.97	C24—C25	1.367 (3)
C6—H6A	0.96	C24—Cl2	1.747 (2)
C6—H6B	0.96	C25—C26	1.384 (3)
C6—H6C	0.96	C25—H25	0.93
C11—C12	1.383 (3)	C26—H26	0.93
N1—C1—N2	111.86 (19)	C13—C12—H12	119.3
N1—C1—H1A	109.2	C14—C13—C12	119.6 (2)
N2—C1—H1A	109.2	C14—C13—H13	120.2
N1—C1—H1B	109.2	C12—C13—H13	120.2
N2—C1—H1B	109.2	C15—C14—C13	120.5 (2)
H1A—C1—H1B	107.9	C15—C14—Cl1	119.76 (19)
N2—C2—N3	111.81 (18)	C13—C14—Cl1	119.70 (19)
N2—C2—H2A	109.3	C14—C15—C16	119.6 (2)
N3—C2—H2A	109.3	C14—C15—H15	120.2
N2—C2—H2B	109.3	C16—C15—H15	120.2
N3—C2—H2B	109.3	C15—C16—C11	121.7 (2)
H2A—C2—H2B	107.9	C15—C16—H16	119.1
N1—C3—N3	112.04 (19)	C11—C16—H16	119.1
N1—C3—H3A	109.2	C26—C21—C22	117.6 (2)
N3—C3—H3A	109.2	C26—C21—N2	123.0 (2)
N1—C3—H3B	109.2	C22—C21—N2	119.3 (2)
N3—C3—H3B	109.2	C23—C22—C21	121.4 (2)
H3A—C3—H3B	107.9	C23—C22—H22	119.3
C5—C4—N3	113.4 (3)	C21—C22—H22	119.3
C5—C4—H4A	108.9	C24—C23—C22	119.4 (2)
N3—C4—H4A	108.9	C24—C23—H23	120.3
C5—C4—H4B	108.9	C22—C23—H23	120.3
N3—C4—H4B	108.9	C25—C24—C23	120.9 (2)
H4A—C4—H4B	107.7	C25—C24—Cl2	119.54 (19)
C4—C5—C6	112.8 (3)	C23—C24—Cl2	119.48 (19)
C4—C5—H5A	109	C24—C25—C26	119.5 (2)
C6—C5—H5A	109	C24—C25—H25	120.2
C4—C5—H5B	109	C26—C25—H25	120.2
C6—C5—H5B	109	C25—C26—C21	121.2 (2)
H5A—C5—H5B	107.8	C25—C26—H26	119.4
C5—C6—H6A	109.5	C21—C26—H26	119.4
C5—C6—H6B	109.5	C11—N1—C3	118.73 (19)
H6A—C6—H6B	109.5	C11—N1—C1	118.44 (19)
C5—C6—H6C	109.5	C3—N1—C1	109.38 (19)
H6A—C6—H6C	109.5	C21—N2—C2	118.41 (19)
H6B—C6—H6C	109.5	C21—N2—C1	118.07 (18)
C12—C11—C16	117.3 (2)	C2—N2—C1	109.76 (19)
C12—C11—N1	123.2 (2)	C2—N3—C3	108.2 (2)
C16—C11—N1	119.4 (2)	C2—N3—C4	108.2 (2)
C11—C12—C13	121.3 (2)	C3—N3—C4	112.7 (2)
C11—C12—H12	119.3
N3—C4—C5—C6	−170.1 (3)	C16—C11—N1—C3	−175.1 (2)
C16—C11—C12—C13	0.7 (3)	C12—C11—N1—C1	−136.1 (2)
N1—C11—C12—C13	−175.0 (2)	C16—C11—N1—C1	48.3 (3)
C11—C12—C13—C14	−0.9 (3)	N3—C3—N1—C11	−83.0 (3)
C12—C13—C14—C15	0.2 (4)	N3—C3—N1—C1	57.2 (3)
C12—C13—C14—Cl1	178.45 (18)	N2—C1—N1—C11	84.7 (2)
C13—C14—C15—C16	0.6 (4)	N2—C1—N1—C3	−55.7 (3)
Cl1—C14—C15—C16	−177.6 (2)	C26—C21—N2—C2	−5.2 (3)
C14—C15—C16—C11	−0.8 (4)	C22—C21—N2—C2	170.6 (2)
C12—C11—C16—C15	0.1 (4)	C26—C21—N2—C1	131.2 (2)
N1—C11—C16—C15	176.0 (2)	C22—C21—N2—C1	−53.0 (3)
C26—C21—C22—C23	1.2 (3)	N3—C2—N2—C21	81.6 (2)
N2—C21—C22—C23	−174.9 (2)	N3—C2—N2—C1	−58.1 (3)
C21—C22—C23—C24	0.4 (4)	N1—C1—N2—C21	−83.5 (3)
C22—C23—C24—C25	−1.4 (4)	N1—C1—N2—C2	56.4 (3)
C22—C23—C24—Cl2	176.34 (19)	N2—C2—N3—C3	58.6 (2)
C23—C24—C25—C26	0.7 (4)	N2—C2—N3—C4	−179.0 (2)
Cl2—C24—C25—C26	−177.02 (17)	N1—C3—N3—C2	−58.3 (3)
C24—C25—C26—C21	0.9 (3)	N1—C3—N3—C4	−177.8 (2)
C22—C21—C26—C25	−1.8 (3)	C5—C4—N3—C2	166.4 (3)
N2—C21—C26—C25	174.05 (19)	C5—C4—N3—C3	−74.0 (4)
C12—C11—N1—C3	0.5 (3)

D—H···A	D—H	H···A	D···A	D—H···A
C2—H2A···Cgi	0.96	2.92	3.668 (3)	134

Table 1

Hydrogen-bond geometry (Å, °)

Cg is centroid of C21–C26 ring.

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C2—H2A⋯Cg i	0.96	2.92	3.668 (3)	134

Symmetry code: (i) .