Crystal structure of 1,2-bis-(2,6-di-methyl-phen-yl)-3-phenyl-guanidine.

In the title compound, C23H25N3, the dihedral angles between the planes of the benzene ring and the two substituent di-methyl-phenyl rings are 60.94 (7)° and 88.08 (7)°, and the dihedral angle between the planes of the two di-methyl-phenyl rings is 58.01 (7)°. In the crystal, weak C-H⋯N inter-actions exist between adjacent mol-ecules. One of the di-methyl-phenyl rings has a small amount of π-π overlap with the phenyl ring of an adjacent mol-ecule [centroid-to-centroid distance = 3.9631 (12) Å].

Related literature

For similar structures of various related compounds, see: Boeré et al. (2000 ▸); Brazeau et al. (2012 ▸); Ghosh et al. (2008 ▸); Han & Huynh (2009 ▸); Chlupatý & Padělková (2014 ▸); Yildirim et al. (2007 ▸); Zhang et al. (2009 ▸). For applications of guanidines, see: Berlinck (2002 ▸); Heys et al. (2000 ▸); Laeckmann et al. (2002 ▸); Kelley et al. (2001 ▸); Moroni et al. (2001 ▸).

Experimental

Crystal data

C23H25N3

M = 343.46

Orthorhombic,

a = 19.003 (7) Å

b = 7.924 (3) Å

c = 13.056 (5) Å

V = 1966.0 (13) Å3

Z = 4

Mo Kα radiation

μ = 0.07 mm−1

T = 194 K

0.35 × 0.33 × 0.30 mm

Data collection

Bruker SMART CCD area-detector diffractometer

Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ▸) T min = 0.976, T max = 0.980

10737 measured reflections

3547 independent reflections

2649 reflections with I > 2σ(I)

R int = 0.038

Refinement

R[F 2 > 2σ(F 2)] = 0.041

wR(F 2) = 0.104

S = 1.02

3547 reflections

239 parameters

1 restraint

H-atom parameters constrained

Δρmax = 0.14 e Å−3

Δρmin = −0.14 e Å−3

Data collection: APEX2 (Bruker, 2007 ▸); cell refinement: SAINT (Bruker, 2007 ▸); 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 ▸).

Crystal structure: contains datablock(s) I. DOI: 10.1107/S2056989015011822/pk2556sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S2056989015011822/pk2556Isup2.hkl

Click here for additional data file.

Supporting information file. DOI: 10.1107/S2056989015011822/pk2556Isup3.cml

Click here for additional data file.

. DOI: 10.1107/S2056989015011822/pk2556fig1.tif

The mol­ecular structure of the title compound. Displacement ellipsoids are drawn at the 50% probability level. H atoms are presented as small spheres of arbitrary radius.

CCDC reference: 1407910

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

C23H25N3	F(000) = 736
Mr = 343.46	Dx = 1.160 Mg m−3
Orthorhombic, Pca21	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2c -2ac	Cell parameters from 2316 reflections
a = 19.003 (7) Å	θ = 2.8–23.5°
b = 7.924 (3) Å	µ = 0.07 mm−1
c = 13.056 (5) Å	T = 194 K
V = 1966.0 (13) Å3	Block, colourless
Z = 4	0.35 × 0.33 × 0.30 mm

Bruker SMART CCD area-detector diffractometer	3547 independent reflections
Radiation source: fine-focus sealed tube	2649 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.038
φ and ω scans	θmax = 25.5°, θmin = 2.7°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −23→23
Tmin = 0.976, Tmax = 0.980	k = −9→5
10737 measured reflections	l = −15→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)] = 0.041	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.104	H-atom parameters constrained
S = 1.01	w = 1/[σ2(Fo2) + (0.0564P)2] where P = (Fo2 + 2Fc2)/3
3547 reflections	(Δ/σ)max = 0.001
239 parameters	Δρmax = 0.14 e Å−3
1 restraint	Δρmin = −0.14 e Å−3

Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds 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
N1	0.51390 (8)	0.8726 (2)	0.22933 (14)	0.0499 (4)
H1	0.5001	0.8129	0.2815	0.060*
N2	0.39761 (8)	0.9417 (2)	0.19326 (13)	0.0470 (4)
N3	0.48706 (8)	1.0319 (2)	0.08715 (13)	0.0494 (5)
H3	0.5300	1.0109	0.0680	0.059*
C1	0.58760 (9)	0.8820 (3)	0.21187 (15)	0.0414 (5)
C2	0.62483 (11)	1.0196 (3)	0.24776 (18)	0.0535 (6)
C3	0.69708 (12)	1.0198 (4)	0.2354 (2)	0.0693 (7)
H3A	0.7238	1.1136	0.2586	0.083*
C4	0.73035 (12)	0.8867 (4)	0.1904 (2)	0.0695 (7)
H4	0.7801	0.8879	0.1840	0.083*
C5	0.69327 (12)	0.7521 (4)	0.15447 (18)	0.0612 (6)
H5	0.7173	0.6614	0.1223	0.073*
C6	0.62094 (10)	0.7464 (3)	0.16442 (17)	0.0482 (5)
C7	0.58943 (16)	1.1640 (3)	0.3014 (2)	0.0825 (8)
H7A	0.5631	1.1213	0.3605	0.124*
H7B	0.5570	1.2202	0.2539	0.124*
H7C	0.6250	1.2448	0.3247	0.124*
C8	0.57928 (15)	0.5980 (3)	0.1261 (2)	0.0732 (7)
H8A	0.5423	0.6375	0.0796	0.110*
H8B	0.5578	0.5392	0.1843	0.110*
H8C	0.6106	0.5204	0.0894	0.110*
C9	0.46259 (9)	0.9480 (3)	0.17228 (15)	0.0392 (4)
C10	0.37336 (10)	0.8594 (3)	0.28195 (16)	0.0470 (5)
C11	0.36221 (11)	0.9503 (4)	0.37126 (18)	0.0592 (7)
C12	0.32944 (14)	0.8739 (5)	0.4525 (2)	0.0830 (9)
H12	0.3214	0.9366	0.5133	0.100*
C13	0.30812 (15)	0.7093 (6)	0.4476 (3)	0.0950 (12)
H13	0.2852	0.6584	0.5044	0.114*
C14	0.32015 (14)	0.6189 (4)	0.3606 (3)	0.0918 (11)
H14	0.3059	0.5041	0.3580	0.110*
C15	0.35250 (11)	0.6897 (3)	0.2757 (2)	0.0628 (7)
C16	0.38379 (16)	1.1319 (4)	0.3781 (2)	0.0814 (9)
H16A	0.3731	1.1888	0.3133	0.122*
H16B	0.4344	1.1389	0.3916	0.122*
H16C	0.3580	1.1868	0.4338	0.122*
C17	0.36204 (16)	0.5931 (4)	0.1775 (3)	0.0942 (10)
H17A	0.3381	0.6526	0.1217	0.141*
H17B	0.3419	0.4799	0.1850	0.141*
H17C	0.4123	0.5839	0.1619	0.141*
C18	0.44829 (10)	1.1495 (3)	0.02788 (14)	0.0437 (5)
C19	0.37790 (11)	1.1326 (3)	0.00775 (16)	0.0546 (6)
H19	0.3529	1.0372	0.0326	0.065*
C20	0.34337 (13)	1.2550 (3)	−0.04892 (17)	0.0641 (7)
H20	0.2943	1.2446	−0.0611	0.077*
C21	0.37888 (15)	1.3896 (3)	−0.0873 (2)	0.0685 (7)
H21	0.3546	1.4731	−0.1258	0.082*
C22	0.44980 (15)	1.4048 (3)	−0.07045 (19)	0.0666 (7)
H22	0.4749	1.4976	−0.0985	0.080*
C23	0.48466 (11)	1.2853 (3)	−0.01269 (16)	0.0533 (5)
H23	0.5338	1.2964	−0.0007	0.064*

	U11	U22	U33	U12	U13	U23
N1	0.0348 (8)	0.0591 (10)	0.0557 (10)	0.0034 (8)	0.0009 (8)	0.0171 (9)
N2	0.0339 (9)	0.0611 (11)	0.0460 (10)	0.0061 (8)	0.0012 (7)	0.0097 (9)
N3	0.0358 (9)	0.0664 (12)	0.0461 (9)	0.0083 (8)	0.0054 (7)	0.0140 (10)
C1	0.0336 (10)	0.0483 (11)	0.0424 (11)	−0.0002 (9)	−0.0060 (8)	0.0072 (10)
C2	0.0533 (12)	0.0528 (13)	0.0543 (13)	−0.0053 (11)	−0.0068 (11)	0.0059 (11)
C3	0.0564 (14)	0.0834 (19)	0.0682 (15)	−0.0248 (14)	−0.0165 (13)	0.0080 (15)
C4	0.0356 (11)	0.111 (2)	0.0622 (15)	−0.0066 (13)	−0.0028 (11)	0.0113 (17)
C5	0.0477 (13)	0.0820 (18)	0.0540 (13)	0.0115 (12)	0.0023 (10)	−0.0007 (13)
C6	0.0432 (11)	0.0551 (13)	0.0461 (11)	0.0001 (10)	−0.0039 (10)	0.0016 (11)
C7	0.0967 (19)	0.0517 (14)	0.099 (2)	0.0000 (14)	−0.0121 (17)	−0.0118 (17)
C8	0.0800 (18)	0.0600 (17)	0.0795 (17)	−0.0056 (14)	−0.0001 (14)	−0.0135 (14)
C9	0.0368 (10)	0.0428 (11)	0.0379 (10)	0.0029 (9)	−0.0032 (9)	−0.0003 (9)
C10	0.0295 (9)	0.0615 (14)	0.0498 (12)	0.0091 (10)	0.0007 (9)	0.0086 (11)
C11	0.0449 (13)	0.0842 (18)	0.0483 (13)	0.0202 (13)	0.0008 (10)	0.0096 (13)
C12	0.0684 (18)	0.127 (3)	0.0534 (15)	0.0326 (18)	0.0107 (13)	0.0181 (18)
C13	0.0656 (17)	0.129 (3)	0.091 (2)	0.0279 (19)	0.0308 (16)	0.058 (2)
C14	0.0606 (16)	0.078 (2)	0.137 (3)	0.0074 (15)	0.0213 (18)	0.044 (2)
C15	0.0420 (12)	0.0628 (15)	0.0837 (17)	0.0046 (11)	0.0078 (12)	0.0096 (15)
C16	0.088 (2)	0.085 (2)	0.0710 (17)	0.0123 (17)	−0.0064 (15)	−0.0176 (17)
C17	0.0784 (18)	0.0710 (18)	0.133 (3)	−0.0084 (15)	0.015 (2)	−0.023 (2)
C18	0.0450 (11)	0.0506 (13)	0.0355 (10)	0.0058 (9)	0.0019 (9)	0.0008 (10)
C19	0.0453 (12)	0.0729 (17)	0.0455 (12)	0.0040 (11)	−0.0026 (9)	0.0083 (12)
C20	0.0533 (13)	0.0902 (19)	0.0487 (12)	0.0137 (13)	−0.0040 (11)	0.0067 (14)
C21	0.0819 (18)	0.0696 (18)	0.0541 (14)	0.0251 (15)	−0.0055 (13)	0.0062 (14)
C22	0.090 (2)	0.0497 (15)	0.0606 (15)	0.0046 (13)	−0.0032 (13)	0.0051 (13)
C23	0.0574 (13)	0.0517 (13)	0.0509 (12)	−0.0007 (11)	−0.0028 (11)	−0.0014 (12)

N1—C9	1.365 (2)	C11—C12	1.370 (4)
N1—C1	1.421 (2)	C11—C16	1.499 (4)
N1—H1	0.8700	C12—C13	1.368 (5)
N2—C9	1.266 (2)	C12—H12	0.9500
N2—C10	1.407 (3)	C13—C14	1.363 (5)
N3—C9	1.376 (2)	C13—H13	0.9500
N3—C18	1.418 (3)	C14—C15	1.386 (4)
N3—H3	0.8699	C14—H14	0.9500
C1—C2	1.381 (3)	C15—C17	1.503 (4)
C1—C6	1.393 (3)	C16—H16A	0.9800
C2—C3	1.382 (3)	C16—H16B	0.9800
C2—C7	1.501 (4)	C16—H16C	0.9800
C3—C4	1.363 (4)	C17—H17A	0.9800
C3—H3A	0.9500	C17—H17B	0.9800
C4—C5	1.362 (3)	C17—H17C	0.9800
C4—H4	0.9500	C18—C19	1.370 (3)
C5—C6	1.381 (3)	C18—C23	1.385 (3)
C5—H5	0.9500	C19—C20	1.385 (3)
C6—C8	1.503 (3)	C19—H19	0.9500
C7—H7A	0.9800	C20—C21	1.358 (3)
C7—H7B	0.9800	C20—H20	0.9500
C7—H7C	0.9800	C21—C22	1.371 (4)
C8—H8A	0.9800	C21—H21	0.9500
C8—H8B	0.9800	C22—C23	1.380 (3)
C8—H8C	0.9800	C22—H22	0.9500
C10—C11	1.387 (3)	C23—H23	0.9500
C10—C15	1.405 (3)
C9—N1—C1	126.42 (17)	C12—C11—C16	120.2 (3)
C9—N1—H1	116.8	C10—C11—C16	120.5 (2)
C1—N1—H1	116.8	C13—C12—C11	121.3 (3)
C9—N2—C10	121.07 (16)	C13—C12—H12	119.3
C9—N3—C18	125.64 (16)	C11—C12—H12	119.3
C9—N3—H3	117.2	C14—C13—C12	119.3 (3)
C18—N3—H3	117.2	C14—C13—H13	120.3
C2—C1—C6	121.78 (17)	C12—C13—H13	120.3
C2—C1—N1	119.46 (19)	C13—C14—C15	121.9 (3)
C6—C1—N1	118.63 (17)	C13—C14—H14	119.0
C1—C2—C3	118.0 (2)	C15—C14—H14	119.0
C1—C2—C7	122.0 (2)	C14—C15—C10	117.8 (3)
C3—C2—C7	119.9 (2)	C14—C15—C17	122.0 (3)
C4—C3—C2	120.7 (2)	C10—C15—C17	120.2 (2)
C4—C3—H3A	119.7	C11—C16—H16A	109.5
C2—C3—H3A	119.7	C11—C16—H16B	109.5
C5—C4—C3	121.0 (2)	H16A—C16—H16B	109.5
C5—C4—H4	119.5	C11—C16—H16C	109.5
C3—C4—H4	119.5	H16A—C16—H16C	109.5
C4—C5—C6	120.5 (2)	H16B—C16—H16C	109.5
C4—C5—H5	119.7	C15—C17—H17A	109.5
C6—C5—H5	119.7	C15—C17—H17B	109.5
C5—C6—C1	118.0 (2)	H17A—C17—H17B	109.5
C5—C6—C8	121.2 (2)	C15—C17—H17C	109.5
C1—C6—C8	120.80 (18)	H17A—C17—H17C	109.5
C2—C7—H7A	109.5	H17B—C17—H17C	109.5
C2—C7—H7B	109.5	C19—C18—C23	119.3 (2)
H7A—C7—H7B	109.5	C19—C18—N3	123.2 (2)
C2—C7—H7C	109.5	C23—C18—N3	117.43 (18)
H7A—C7—H7C	109.5	C18—C19—C20	119.8 (2)
H7B—C7—H7C	109.5	C18—C19—H19	120.1
C6—C8—H8A	109.5	C20—C19—H19	120.1
C6—C8—H8B	109.5	C21—C20—C19	120.8 (2)
H8A—C8—H8B	109.5	C21—C20—H20	119.6
C6—C8—H8C	109.5	C19—C20—H20	119.6
H8A—C8—H8C	109.5	C20—C21—C22	119.9 (2)
H8B—C8—H8C	109.5	C20—C21—H21	120.1
N2—C9—N1	124.15 (18)	C22—C21—H21	120.1
N2—C9—N3	121.58 (17)	C21—C22—C23	120.0 (2)
N1—C9—N3	114.26 (16)	C21—C22—H22	120.0
C11—C10—C15	120.2 (2)	C23—C22—H22	120.0
C11—C10—N2	120.1 (2)	C22—C23—C18	120.2 (2)
C15—C10—N2	119.2 (2)	C22—C23—H23	119.9
C12—C11—C10	119.4 (3)	C18—C23—H23	119.9
C9—N1—C1—C2	82.9 (3)	C15—C10—C11—C12	−1.3 (3)
C9—N1—C1—C6	−101.1 (2)	N2—C10—C11—C12	170.91 (19)
C6—C1—C2—C3	0.0 (3)	C15—C10—C11—C16	−179.4 (2)
N1—C1—C2—C3	175.9 (2)	N2—C10—C11—C16	−7.3 (3)
C6—C1—C2—C7	−178.4 (2)	C10—C11—C12—C13	0.7 (4)
N1—C1—C2—C7	−2.5 (3)	C16—C11—C12—C13	178.9 (3)
C1—C2—C3—C4	−0.9 (4)	C11—C12—C13—C14	0.5 (4)
C7—C2—C3—C4	177.5 (2)	C12—C13—C14—C15	−1.0 (5)
C2—C3—C4—C5	1.4 (4)	C13—C14—C15—C10	0.4 (4)
C3—C4—C5—C6	−1.0 (4)	C13—C14—C15—C17	−176.4 (3)
C4—C5—C6—C1	0.1 (3)	C11—C10—C15—C14	0.7 (3)
C4—C5—C6—C8	−179.4 (2)	N2—C10—C15—C14	−171.5 (2)
C2—C1—C6—C5	0.4 (3)	C11—C10—C15—C17	177.6 (2)
N1—C1—C6—C5	−175.5 (2)	N2—C10—C15—C17	5.4 (3)
C2—C1—C6—C8	179.9 (2)	C9—N3—C18—C19	−37.2 (3)
N1—C1—C6—C8	4.0 (3)	C9—N3—C18—C23	144.1 (2)
C10—N2—C9—N1	2.6 (3)	C23—C18—C19—C20	−2.8 (3)
C10—N2—C9—N3	−178.32 (19)	N3—C18—C19—C20	178.5 (2)
C1—N1—C9—N2	−177.0 (2)	C18—C19—C20—C21	1.8 (3)
C1—N1—C9—N3	3.9 (3)	C19—C20—C21—C22	0.3 (4)
C18—N3—C9—N2	15.3 (3)	C20—C21—C22—C23	−1.4 (4)
C18—N3—C9—N1	−165.6 (2)	C21—C22—C23—C18	0.4 (4)
C9—N2—C10—C11	94.0 (2)	C19—C18—C23—C22	1.8 (3)
C9—N2—C10—C15	−93.7 (2)	N3—C18—C23—C22	−179.54 (19)

D—H···A	D—H	H···A	D···A	D—H···A
C4—H4···N2i	0.95	2.61	3.457 (3)	148

Table 1

Hydrogen-bond geometry (, )

DHA	DH	HA	D A	DHA
C4H4N2i	0.95	2.61	3.457(3)	148

Symmetry code: (i) .