(Z)-2-Phenyl-3-pivaloyl-1,1-dipropyl-guanidine.

In the title compound, C(18)H(29)N(3)O, a polysubstituted guanidine, the torsion angles indicate that the guanidine unit and the carbonyl group are almost perpendicular to one another [O-C-N-C= -7.40 (18), C-N-C-N= -97.21 (15) and 86.41 (13)°]. The crystal packing is stablized by inter-molecular N-H⋯O hydrogen bonds, which link the mol-ecules into a chain.

Related literature

For the biological and chemical properties of guanidine derivatives, see: Ohara et al. (2007 ▶); Berlinck (2002 ▶); Ma et al. (2008 ▶); Brzozowski et al. (2007 ▶); Gomez et al. (2000 ▶); Kovacevic & Maksic (2001 ▶); Ishikawa & Isobe (2002 ▶); Rauf et al. (2009 ▶). For related structures, see: Cunha et al. (2005 ▶); Murtaza et al. (2007 ▶, 2008 ▶, 2009 ▶).

Experimental

Crystal data

C18H29N3O

M = 303.44

Orthorhombic,

a = 9.898 (5) Å

b = 12.648 (5) Å

c = 15.126 (5) Å

V = 1893.6 (14) Å3

Z = 4

Mo Kα radiation

μ = 0.07 mm−1

T = 183 K

0.42 × 0.42 × 0.32 mm

Data collection

Oxford diffraction Xcalibur R diffractometer

Absorption correction: multi-scan (CrysAlis RED; Oxford Diffraction, 2006 ▶) T min = 0.973, T max = 0.979

31051 measured reflections

7202 independent reflections

5107 reflections with I > 2σ(I)

R int = 0.029

Refinement

R[F 2 > 2σ(F 2)] = 0.056

wR(F 2) = 0.134

S = 0.97

7202 reflections

211 parameters

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.30 e Å−3

Δρmin = −0.18 e Å−3

Absolute structure: Flack (1983 ▶),3174 Friedel pairs

Flack parameter: 0.20 (12)

Data collection: CrysAlis CCD (Oxford Diffraction, 2006 ▶); cell refinement: CrysAlis RED (Oxford Diffraction, 2006 ▶); data reduction: CrysAlis RED; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: ORTEP-3 (Farrugia, 1997 ▶); software used to prepare material for publication: SHELXL97.

Crystal structure: contains datablocks I, global. DOI: 10.1107/S160053680902978X/su2130sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S160053680902978X/su2130Isup2.hkl

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

C18H29N3O	F(000) = 664
Mr = 303.44	Dx = 1.064 Mg m−3
Orthorhombic, P212121	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2ac 2ab	Cell parameters from 31051 reflections
a = 9.898 (5) Å	θ = 2.5–33.1°
b = 12.648 (5) Å	µ = 0.07 mm−1
c = 15.126 (5) Å	T = 183 K
V = 1893.6 (14) Å3	Block, colourless
Z = 4	0.42 × 0.42 × 0.32 mm

Oxford diffraction Xcalibur R diffractometer	7202 independent reflections
Radiation source: Enhance (Mo) X-ray Source	5107 reflections with I > 2σ(I)
graphite	Rint = 0.029
Detector resolution: 10.4498 pixels mm-1	θmax = 33.1°, θmin = 2.5°
Profile data from ω scans	h = −14→15
Absorption correction: multi-scan (CrysAlis RED; Oxford Diffraction, 2006)	k = −19→19
Tmin = 0.973, Tmax = 0.979	l = −23→23
31051 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)] = 0.056	H atoms treated by a mixture of independent and constrained refinement
wR(F2) = 0.134	w = 1/[σ2(Fo2) + (0.0786P)2] where P = (Fo2 + 2Fc2)/3
S = 0.97	(Δ/σ)max < 0.001
7202 reflections	Δρmax = 0.30 e Å−3
211 parameters	Δρmin = −0.18 e Å−3
0 restraints	Absolute structure: Flack (1983), 3174 Friedel pairs
Primary atom site location: structure-invariant direct methods	Flack parameter: 0.20 (12)

Experimental. Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm CrysAlis RED (Oxford Diffraction, 2006)

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
N1	0.64742 (9)	0.28579 (7)	0.00092 (7)	0.02445 (18)
H1	0.5657 (17)	0.2689 (11)	0.0027 (9)	0.031 (3)*
N3	0.67372 (13)	0.43416 (8)	0.09671 (7)	0.0375 (3)
N11	0.71989 (11)	0.45147 (7)	−0.05199 (7)	0.0299 (2)
C11A	0.74991 (15)	0.56368 (9)	−0.03790 (10)	0.0386 (3)
H11A	0.8100	0.5889	−0.0858	0.080*
H11B	0.7988	0.5719	0.0188	0.080*
C12A	0.62283 (18)	0.63189 (11)	−0.03603 (12)	0.0520 (4)
H12A	0.5797	0.6314	−0.0951	0.080*
H12B	0.5578	0.6023	0.0070	0.080*
C13A	0.6579 (2)	0.74502 (11)	−0.01020 (13)	0.0614 (5)
H13A	0.7048	0.7450	0.0469	0.0803 (17)*
H13B	0.5748	0.7867	−0.0055	0.0803 (17)*
H13C	0.7166	0.7761	−0.0554	0.0803 (17)*
C11B	0.72858 (13)	0.40828 (10)	−0.14124 (8)	0.0331 (3)
H11C	0.7649	0.3355	−0.1376	0.080*
H11D	0.7938	0.4511	−0.1755	0.080*
C12B	0.59584 (17)	0.40521 (13)	−0.19124 (10)	0.0459 (3)
H12C	0.5610	0.4780	−0.1986	0.080*
H12D	0.5286	0.3644	−0.1569	0.080*
C13B	0.6147 (2)	0.35420 (16)	−0.28203 (11)	0.0632 (5)
H13D	0.6810	0.3948	−0.3161	0.0803 (17)*
H13E	0.5282	0.3536	−0.3136	0.0803 (17)*
H13F	0.6471	0.2815	−0.2746	0.0803 (17)*
O1	0.86233 (8)	0.23044 (7)	0.00147 (7)	0.0390 (2)
C2	0.68297 (11)	0.39354 (8)	0.01936 (8)	0.0265 (2)
C3	0.74191 (11)	0.20881 (8)	−0.00239 (8)	0.0271 (2)
C21	0.68941 (12)	0.09564 (9)	−0.01267 (10)	0.0366 (3)
C22	0.6283 (2)	0.08507 (15)	−0.10465 (14)	0.0698 (6)
H22A	0.5525	0.1344	−0.1107	0.0803 (17)*
H22B	0.5960	0.0126	−0.1133	0.0803 (17)*
H22C	0.6971	0.1015	−0.1491	0.0803 (17)*
C23	0.80917 (14)	0.02055 (10)	−0.00221 (14)	0.0550 (4)
H23A	0.8782	0.0377	−0.0464	0.0803 (17)*
H23B	0.7787	−0.0525	−0.0107	0.0803 (17)*
H23C	0.8475	0.0283	0.0572	0.0803 (17)*
C24	0.58315 (17)	0.07004 (12)	0.05771 (15)	0.0597 (5)
H24A	0.6207	0.0838	0.1166	0.0803 (17)*
H24B	0.5574	−0.0046	0.0532	0.0803 (17)*
H24C	0.5033	0.1145	0.0484	0.0803 (17)*
C31	0.64035 (15)	0.36809 (11)	0.16887 (8)	0.0377 (3)
C32	0.51984 (17)	0.38671 (15)	0.21422 (10)	0.0513 (4)
H32	0.4640	0.4448	0.1983	0.070 (3)*
C33	0.4819 (2)	0.31964 (17)	0.28296 (11)	0.0613 (5)
H33	0.3985	0.3310	0.3124	0.070 (3)*
C34	0.5638 (2)	0.23707 (16)	0.30876 (11)	0.0648 (5)
H34	0.5363	0.1906	0.3547	0.070 (3)*
C35	0.6853 (2)	0.22300 (16)	0.26725 (10)	0.0650 (5)
H35	0.7439	0.1679	0.2860	0.070 (3)*
C36	0.72416 (19)	0.28850 (15)	0.19788 (11)	0.0530 (4)
H36	0.8093	0.2782	0.1703	0.070 (3)*

	U11	U22	U33	U12	U13	U23
N1	0.0163 (4)	0.0234 (4)	0.0336 (5)	−0.0025 (3)	0.0004 (4)	0.0011 (4)
N3	0.0474 (7)	0.0315 (5)	0.0335 (5)	−0.0081 (5)	0.0063 (5)	−0.0019 (4)
N11	0.0322 (5)	0.0245 (4)	0.0329 (5)	−0.0028 (4)	0.0041 (4)	0.0026 (4)
C11A	0.0450 (8)	0.0240 (5)	0.0469 (7)	−0.0079 (5)	0.0106 (6)	0.0021 (5)
C12A	0.0585 (10)	0.0288 (6)	0.0687 (10)	0.0005 (6)	0.0091 (8)	−0.0044 (6)
C13A	0.0930 (13)	0.0275 (6)	0.0637 (10)	−0.0057 (7)	0.0275 (10)	−0.0062 (6)
C11B	0.0347 (6)	0.0330 (5)	0.0316 (6)	−0.0006 (5)	0.0067 (5)	0.0056 (5)
C12B	0.0480 (8)	0.0471 (8)	0.0427 (7)	0.0090 (6)	−0.0081 (7)	0.0005 (7)
C13B	0.0798 (13)	0.0689 (11)	0.0409 (9)	0.0042 (10)	−0.0133 (9)	−0.0021 (8)
O1	0.0181 (4)	0.0343 (4)	0.0647 (6)	−0.0013 (3)	0.0010 (4)	0.0017 (5)
C2	0.0207 (5)	0.0247 (5)	0.0340 (6)	−0.0016 (4)	0.0005 (4)	0.0011 (4)
C3	0.0194 (5)	0.0260 (4)	0.0358 (6)	−0.0018 (4)	0.0006 (5)	0.0030 (5)
C21	0.0234 (5)	0.0243 (5)	0.0621 (8)	−0.0007 (4)	−0.0032 (6)	0.0000 (5)
C22	0.0741 (13)	0.0471 (9)	0.0882 (14)	−0.0103 (8)	−0.0347 (11)	−0.0170 (9)
C23	0.0337 (7)	0.0287 (6)	0.1028 (14)	0.0057 (5)	−0.0018 (9)	−0.0006 (8)
C24	0.0383 (8)	0.0322 (7)	0.1086 (15)	−0.0060 (6)	0.0181 (9)	0.0162 (8)
C31	0.0472 (8)	0.0387 (7)	0.0271 (6)	−0.0112 (6)	0.0022 (5)	−0.0056 (5)
C32	0.0471 (9)	0.0683 (11)	0.0384 (8)	−0.0075 (8)	0.0036 (7)	0.0031 (7)
C33	0.0550 (10)	0.0903 (14)	0.0387 (8)	−0.0193 (10)	0.0083 (8)	0.0046 (8)
C34	0.0904 (14)	0.0744 (12)	0.0296 (7)	−0.0249 (11)	0.0002 (9)	0.0103 (8)
C35	0.0958 (15)	0.0657 (11)	0.0334 (7)	0.0116 (11)	−0.0007 (9)	0.0094 (7)
C36	0.0615 (10)	0.0613 (9)	0.0364 (7)	0.0057 (8)	0.0063 (7)	0.0039 (7)

N1—C3	1.3510 (14)	O1—C3	1.2243 (15)
N1—C2	1.4348 (15)	C3—C21	1.5307 (16)
N1—H1	0.837 (17)	C21—C22	1.522 (2)
N3—C2	1.2812 (16)	C21—C23	1.5270 (18)
N3—C31	1.4140 (17)	C21—C24	1.532 (2)
N11—C2	1.3548 (15)	C22—H22A	0.9800
N11—C11B	1.4590 (17)	C22—H22B	0.9800
N11—C11A	1.4656 (16)	C22—H22C	0.9800
C11A—C12A	1.526 (2)	C23—H23A	0.9800
C11A—H11A	0.9900	C23—H23B	0.9800
C11A—H11B	0.9900	C23—H23C	0.9800
C12A—C13A	1.523 (2)	C24—H24A	0.9800
C12A—H12A	0.9900	C24—H24B	0.9800
C12A—H12B	0.9900	C24—H24C	0.9800
C13A—H13A	0.9800	C31—C36	1.376 (2)
C13A—H13B	0.9800	C31—C32	1.396 (2)
C13A—H13C	0.9800	C32—C33	1.394 (2)
C11B—C12B	1.516 (2)	C32—H32	0.9500
C11B—H11C	0.9900	C33—C34	1.378 (3)
C11B—H11D	0.9900	C33—H33	0.9500
C12B—C13B	1.529 (2)	C34—C35	1.369 (3)
C12B—H12C	0.9900	C34—H34	0.9500
C12B—H12D	0.9900	C35—C36	1.391 (3)
C13B—H13D	0.9800	C35—H35	0.9500
C13B—H13E	0.9800	C36—H36	0.9500
C13B—H13F	0.9800
C3—N1—C2	121.47 (9)	O1—C3—N1	120.74 (10)
C3—N1—H1	119.1 (9)	O1—C3—C21	122.97 (10)
C2—N1—H1	118.2 (9)	N1—C3—C21	116.28 (10)
C2—N3—C31	119.01 (10)	C22—C21—C23	110.35 (15)
C2—N11—C11B	123.42 (10)	C22—C21—C24	110.14 (15)
C2—N11—C11A	117.56 (10)	C23—C21—C24	109.27 (13)
C11B—N11—C11A	119.01 (10)	C22—C21—C3	108.02 (12)
N11—C11A—C12A	112.54 (12)	C23—C21—C3	107.92 (10)
N11—C11A—H11A	109.1	C24—C21—C3	111.11 (12)
C12A—C11A—H11A	109.1	C21—C22—H22A	109.5
N11—C11A—H11B	109.1	C21—C22—H22B	109.5
C12A—C11A—H11B	109.1	H22A—C22—H22B	109.5
H11A—C11A—H11B	107.8	C21—C22—H22C	109.5
C13A—C12A—C11A	110.38 (15)	H22A—C22—H22C	109.5
C13A—C12A—H12A	109.6	H22B—C22—H22C	109.5
C11A—C12A—H12A	109.6	C21—C23—H23A	109.5
C13A—C12A—H12B	109.6	C21—C23—H23B	109.5
C11A—C12A—H12B	109.6	H23A—C23—H23B	109.5
H12A—C12A—H12B	108.1	C21—C23—H23C	109.5
C12A—C13A—H13A	109.5	H23A—C23—H23C	109.5
C12A—C13A—H13B	109.5	H23B—C23—H23C	109.5
H13A—C13A—H13B	109.5	C21—C24—H24A	109.5
C12A—C13A—H13C	109.5	C21—C24—H24B	109.5
H13A—C13A—H13C	109.5	H24A—C24—H24B	109.5
H13B—C13A—H13C	109.5	C21—C24—H24C	109.5
N11—C11B—C12B	114.80 (11)	H24A—C24—H24C	109.5
N11—C11B—H11C	108.6	H24B—C24—H24C	109.5
C12B—C11B—H11C	108.6	C36—C31—C32	118.80 (14)
N11—C11B—H11D	108.6	C36—C31—N3	122.50 (14)
C12B—C11B—H11D	108.6	C32—C31—N3	118.67 (14)
H11C—C11B—H11D	107.5	C33—C32—C31	119.64 (17)
C11B—C12B—C13B	110.64 (14)	C33—C32—H32	120.2
C11B—C12B—H12C	109.5	C31—C32—H32	120.2
C13B—C12B—H12C	109.5	C34—C33—C32	120.91 (18)
C11B—C12B—H12D	109.5	C34—C33—H33	119.5
C13B—C12B—H12D	109.5	C32—C33—H33	119.5
H12C—C12B—H12D	108.1	C35—C34—C33	119.04 (17)
C12B—C13B—H13D	109.5	C35—C34—H34	120.5
C12B—C13B—H13E	109.5	C33—C34—H34	120.5
H13D—C13B—H13E	109.5	C34—C35—C36	120.78 (19)
C12B—C13B—H13F	109.5	C34—C35—H35	119.6
H13D—C13B—H13F	109.5	C36—C35—H35	119.6
H13E—C13B—H13F	109.5	C31—C36—C35	120.62 (17)
N3—C2—N11	122.01 (10)	C31—C36—H36	119.7
N3—C2—N1	122.72 (10)	C35—C36—H36	119.7
N11—C2—N1	115.16 (10)
C2—N11—C11A—C12A	−82.33 (15)	O1—C3—C21—C22	−110.60 (16)
C11B—N11—C11A—C12A	96.56 (14)	N1—C3—C21—C22	68.37 (16)
N11—C11A—C12A—C13A	173.14 (13)	O1—C3—C21—C23	8.71 (19)
C2—N11—C11B—C12B	83.80 (15)	N1—C3—C21—C23	−172.32 (13)
C11A—N11—C11B—C12B	−95.02 (14)	O1—C3—C21—C24	128.49 (15)
N11—C11B—C12B—C13B	−177.43 (13)	N1—C3—C21—C24	−52.54 (16)
C31—N3—C2—N11	−177.27 (12)	C2—N3—C31—C36	65.47 (19)
C31—N3—C2—N1	6.59 (19)	C2—N3—C31—C32	−116.74 (15)
C11B—N11—C2—N3	−178.62 (12)	C36—C31—C32—C33	−5.0 (2)
C11A—N11—C2—N3	0.21 (18)	N3—C31—C32—C33	177.09 (14)
C11B—N11—C2—N1	−2.21 (16)	C31—C32—C33—C34	2.1 (3)
C11A—N11—C2—N1	176.62 (10)	C32—C33—C34—C35	1.6 (3)
C3—N1—C2—N3	−97.25 (15)	C33—C34—C35—C36	−2.3 (3)
C3—N1—C2—N11	86.36 (13)	C32—C31—C36—C35	4.4 (2)
C2—N1—C3—O1	−7.40 (18)	N3—C31—C36—C35	−177.80 (15)
C2—N1—C3—C21	173.61 (12)	C34—C35—C36—C31	−0.8 (3)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1···O1i	0.837 (17)	2.01 (2)	2.830 (2)	165 (1)

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1⋯O1i	0.837 (17)	2.01 (2)	2.830 (2)	165 (1)

Symmetry code: (i) .