(2R,5S)-5-Benzyl-2,3-dimethyl-4-oxo-2-phenyl-imidazolidin-1-ium chloride.

The title hydro-chloride salt, C(18)H(21)N(2)O(+)·Cl(-), is an imidazolidinone catalyst, which was derived from L-phenyl-alanine through cyclization with acetophenone. The imidazolidinone compound has a five-membered heterocyclic ring including two chiral centres. The imidazolidinone ring displays an envelope conformation, with the flap protonated N atom lying 0.497 (3) Å above the mean plane of the remaining four atoms. In the crystal structure, one-dimensional supra-molecular chains parallel to the crystallographic 2(1) screw axis are formed by N-H⋯Cl hydrogen bonds involving the NH(2) (+) and Cl(-) groups. Intra-molecular N-H⋯Cl inter-actions are also present.

Related literature

For chiral secondary amine catalysts based on the imidazolidinone architecture, see: Ouellet et al. (2007 ▶). For Michael additions of aldehydes to enones with a MacMillan imidazol­idinone catalyst, see: Hechavarria Fonseca & List (2004 ▶).

Experimental

Crystal data

C18H21N2O+·Cl−

M = 316.83

Monoclinic,

a = 10.5797 (11) Å

b = 7.5876 (7) Å

c = 10.8741 (12) Å

β = 105.516 (3)°

V = 841.10 (15) Å3

Z = 2

Mo Kα radiation

μ = 0.23 mm−1

T = 296 K

0.34 × 0.26 × 0.11 mm

Data collection

Rigaku R-AXIS RAPID diffractometer

Absorption correction: multi-scan (ABSCOR; Higashi, 1995 ▶) T min = 0.920, T max = 0.975

8064 measured reflections

3371 independent reflections

2933 reflections with F 2 > 2σ(F 2)

R int = 0.024

Refinement

R[F 2 > 2σ(F 2)] = 0.030

wR(F 2) = 0.073

S = 1.00

3371 reflections

201 parameters

H-atom parameters constrained

Δρmax = 0.32 e Å−3

Δρmin = −0.30 e Å−3

Absolute structure: Flack (1983 ▶), 1323 Friedel pairs

Flack parameter: 0.03 (4)

Data collection: PROCESS-AUTO (Rigaku, 1998 ▶); cell refinement: PROCESS-AUTO; data reduction: CrystalStructure (Rigaku/MSC, 2004 ▶); program(s) used to solve structure: SIR97 (Altomare et al., 1999 ▶); program(s) used to refine structure: CRYSTALS (Betteridge et al., 2003 ▶); molecular graphics: ORTEPIII (Burnett & Johnson, 1996 ▶); software used to prepare material for publication: CRYSTALS.

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536809010460/bh2221sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536809010460/bh2221Isup2.hkl

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

C18H21N2O+·Cl−	F(000) = 336.00
Mr = 316.83	Dx = 1.251 Mg m−3
Monoclinic, P21	Mo Kα radiation, λ = 0.71075 Å
Hall symbol: P 2yb	Cell parameters from 5642 reflections
a = 10.5797 (11) Å	θ = 3.1–27.4°
b = 7.5876 (7) Å	µ = 0.23 mm−1
c = 10.8741 (12) Å	T = 296 K
β = 105.516 (3)°	Needle, colourless
V = 841.10 (15) Å3	0.34 × 0.26 × 0.11 mm
Z = 2

Rigaku R-AXIS RAPID diffractometer	2933 reflections with F2 > 2σ(F2)
Detector resolution: 10.00 pixels mm-1	Rint = 0.024
ω scans	θmax = 27.4°
Absorption correction: multi-scan (ABSCOR; Higashi, 1995)	h = −13→13
Tmin = 0.920, Tmax = 0.975	k = −8→9
8064 measured reflections	l = −14→14
3371 independent reflections

Refinement on F2	(Δ/σ)max < 0.001
R[F2 > 2σ(F2)] = 0.030	Δρmax = 0.32 e Å−3
wR(F2) = 0.073	Δρmin = −0.30 e Å−3
S = 1.00	Extinction correction: CRYSTALS (Betteridge et al., 2003)
3371 reflections	Extinction coefficient: 148 (16)
201 parameters	Absolute structure: Flack (1983), 1323 Friedel pairs
H-atom parameters constrained	Flack parameter: 0.03 (4)
w = 1/[0.0003Fo2 + 1.04σ(Fo2)]/(4Fo2)

	x	y	z	Uiso*/Ueq
Cl1	0.93865 (4)	0.37096 (8)	0.38333 (4)	0.04566 (11)
O1	0.55546 (12)	0.94486 (19)	0.53994 (12)	0.0482 (3)
N1	0.66144 (12)	0.93555 (17)	0.38197 (12)	0.0328 (3)
N2	0.80291 (11)	0.70805 (17)	0.45120 (12)	0.0282 (3)
C1	0.70374 (14)	0.7044 (2)	0.52767 (14)	0.0300 (4)
C2	0.63026 (12)	0.8761 (2)	0.48651 (13)	0.0329 (3)
C3	0.73966 (14)	0.8101 (2)	0.33039 (14)	0.0299 (3)
C4	0.6042 (2)	1.0933 (2)	0.3114 (2)	0.0506 (5)
C5	0.84477 (16)	0.9014 (2)	0.28214 (17)	0.0433 (5)
C6	0.65243 (14)	0.6841 (2)	0.23338 (14)	0.0308 (4)
C7	0.70586 (18)	0.5811 (2)	0.15399 (17)	0.0424 (5)
C8	0.6288 (2)	0.4612 (2)	0.07068 (18)	0.0539 (6)
C9	0.4987 (2)	0.4414 (2)	0.06476 (19)	0.0538 (5)
C10	0.44421 (19)	0.5420 (2)	0.14153 (19)	0.0506 (5)
C11	0.51948 (16)	0.6636 (2)	0.22594 (16)	0.0395 (4)
C12	0.76199 (17)	0.6939 (2)	0.67155 (14)	0.0353 (4)
C13	0.80340 (14)	0.5137 (2)	0.72774 (17)	0.0347 (4)
C14	0.8565 (2)	0.4999 (2)	0.8593 (2)	0.0530 (5)
C15	0.8969 (2)	0.3397 (3)	0.9158 (2)	0.0684 (7)
C16	0.8867 (2)	0.1899 (3)	0.8436 (2)	0.0618 (6)
C17	0.8346 (2)	0.2009 (2)	0.7136 (2)	0.0582 (6)
C18	0.79285 (17)	0.3619 (2)	0.65706 (18)	0.0467 (4)
H1	0.6438	0.6050	0.4996	0.036*
H7	0.7941	0.5929	0.1569	0.051*
H8	0.6658	0.3932	0.0182	0.065*
H9	0.4478	0.3602	0.0089	0.065*
H10	0.3557	0.5289	0.1373	0.061*
H11	0.4811	0.7314	0.2775	0.047*
H14	0.8647	0.6005	0.9097	0.064*
H15	0.9314	0.3332	1.0038	0.082*
H16	0.9148	0.0821	0.8819	0.074*
H17	0.8274	0.1001	0.6636	0.070*
H18	0.7568	0.3672	0.5692	0.056*
H41	0.5471	1.1496	0.3547	0.061*
H42	0.5549	1.0606	0.2269	0.061*
H43	0.6729	1.1732	0.3063	0.061*
H51	0.8041	0.9742	0.2103	0.052*
H52	0.8988	0.8145	0.2568	0.052*
H53	0.8980	0.9732	0.3489	0.052*
H121	0.6969	0.7390	0.7115	0.042*
H122	0.8388	0.7692	0.6932	0.042*
H201	0.8213	0.6026	0.4327	0.034*
H202	0.8734	0.7600	0.4934	0.034*

	U11	U22	U33	U12	U13	U23
Cl1	0.0397 (2)	0.0372 (2)	0.0553 (2)	0.0126 (2)	0.00437 (17)	−0.0024 (2)
O1	0.0443 (6)	0.0550 (8)	0.0494 (7)	0.0169 (5)	0.0195 (5)	−0.0050 (5)
N1	0.0349 (6)	0.0262 (6)	0.0368 (7)	0.0080 (5)	0.0084 (5)	0.0012 (5)
N2	0.0240 (5)	0.0249 (7)	0.0344 (6)	0.0015 (5)	0.0056 (5)	−0.0035 (5)
C1	0.0271 (7)	0.0279 (8)	0.0354 (8)	−0.0013 (6)	0.0091 (6)	−0.0020 (6)
C2	0.0269 (6)	0.0344 (8)	0.0357 (8)	0.0021 (8)	0.0056 (5)	−0.0057 (8)
C3	0.0289 (7)	0.0261 (8)	0.0340 (8)	0.0033 (6)	0.0074 (6)	0.0013 (6)
C4	0.0570 (11)	0.0356 (10)	0.0565 (12)	0.0167 (9)	0.0107 (9)	0.0075 (8)
C5	0.0408 (8)	0.0405 (11)	0.0521 (10)	−0.0058 (8)	0.0188 (8)	0.0026 (8)
C6	0.0337 (7)	0.0297 (8)	0.0276 (7)	0.0034 (7)	0.0058 (6)	0.0025 (6)
C7	0.0430 (9)	0.0445 (10)	0.0392 (9)	0.0087 (8)	0.0100 (8)	−0.0045 (8)
C8	0.0678 (12)	0.0526 (12)	0.0392 (10)	0.0090 (11)	0.0109 (9)	−0.0113 (9)
C9	0.0638 (12)	0.0493 (11)	0.0408 (10)	−0.0109 (10)	0.0009 (9)	−0.0103 (8)
C10	0.0413 (9)	0.0615 (13)	0.0448 (11)	−0.0121 (9)	0.0042 (8)	−0.0023 (9)
C11	0.0337 (8)	0.0477 (11)	0.0376 (9)	−0.0032 (8)	0.0103 (7)	−0.0031 (8)
C12	0.0388 (8)	0.0333 (9)	0.0342 (8)	−0.0027 (7)	0.0104 (7)	−0.0009 (7)
C13	0.0311 (8)	0.0350 (9)	0.0384 (9)	−0.0029 (7)	0.0100 (7)	0.0036 (7)
C14	0.0629 (12)	0.0495 (12)	0.0408 (10)	−0.0015 (10)	0.0037 (9)	0.0017 (9)
C15	0.0731 (13)	0.0708 (19)	0.0514 (12)	0.0022 (13)	−0.0005 (10)	0.0230 (12)
C16	0.0491 (11)	0.0464 (13)	0.0818 (17)	−0.0030 (10)	0.0035 (11)	0.0232 (12)
C17	0.0566 (11)	0.0342 (11)	0.0807 (15)	−0.0043 (9)	0.0129 (11)	0.0047 (10)
C18	0.0484 (9)	0.0387 (9)	0.0496 (10)	−0.0024 (10)	0.0072 (7)	0.0003 (10)

O1—C2	1.218 (2)	C17—C18	1.385 (2)
N1—C2	1.344 (2)	N2—H201	0.860
N1—C3	1.467 (2)	N2—H202	0.860
N1—C4	1.463 (2)	C1—H1	0.980
N2—C1	1.503 (2)	C4—H41	0.960
N2—C3	1.5176 (19)	C4—H42	0.960
C1—C2	1.521 (2)	C4—H43	0.960
C1—C12	1.523 (2)	C5—H51	0.960
C3—C5	1.518 (2)	C5—H52	0.960
C3—C6	1.536 (2)	C5—H53	0.960
C6—C7	1.392 (2)	C7—H7	0.930
C6—C11	1.396 (2)	C8—H8	0.930
C7—C8	1.385 (2)	C9—H9	0.930
C8—C9	1.368 (3)	C10—H10	0.930
C9—C10	1.367 (3)	C11—H11	0.930
C10—C11	1.392 (2)	C12—H121	0.970
C12—C13	1.514 (2)	C12—H122	0.970
C13—C14	1.394 (2)	C14—H14	0.930
C13—C18	1.373 (2)	C15—H15	0.930
C14—C15	1.378 (3)	C16—H16	0.930
C15—C16	1.369 (3)	C17—H17	0.930
C16—C17	1.375 (3)	C18—H18	0.930
C2—N1—C3	113.37 (13)	C2—C1—H1	109.3
C2—N1—C4	123.90 (16)	C12—C1—H1	109.3
C3—N1—C4	121.80 (15)	N1—C4—H41	109.5
C1—N2—C3	106.07 (11)	N1—C4—H42	109.5
N2—C1—C2	101.48 (12)	N1—C4—H43	109.5
N2—C1—C12	114.76 (12)	H41—C4—H42	109.5
C2—C1—C12	112.44 (13)	H41—C4—H43	109.5
O1—C2—N1	126.71 (16)	H42—C4—H43	109.5
O1—C2—C1	124.95 (15)	C3—C5—H51	109.5
N1—C2—C1	108.34 (14)	C3—C5—H52	109.5
N1—C3—N2	99.40 (12)	C3—C5—H53	109.5
N1—C3—C5	112.12 (13)	H51—C5—H52	109.5
N1—C3—C6	111.70 (12)	H51—C5—H53	109.5
N2—C3—C5	109.75 (11)	H52—C5—H53	109.5
N2—C3—C6	108.76 (12)	C6—C7—H7	119.7
C5—C3—C6	114.07 (14)	C8—C7—H7	119.7
C3—C6—C7	120.44 (14)	C7—C8—H8	119.6
C3—C6—C11	121.35 (15)	C9—C8—H8	119.6
C7—C6—C11	118.15 (14)	C8—C9—H9	120.2
C6—C7—C8	120.59 (18)	C10—C9—H9	120.2
C7—C8—C9	120.8 (2)	C9—C10—H10	119.6
C8—C9—C10	119.57 (18)	C11—C10—H10	119.6
C9—C10—C11	120.81 (18)	C6—C11—H11	119.9
C6—C11—C10	120.13 (17)	C10—C11—H11	119.9
C1—C12—C13	117.13 (14)	C1—C12—H121	107.5
C12—C13—C14	118.38 (16)	C1—C12—H122	107.5
C12—C13—C18	124.10 (15)	C13—C12—H121	107.5
C14—C13—C18	117.52 (17)	C13—C12—H122	107.5
C13—C14—C15	121.02 (19)	H121—C12—H122	109.5
C14—C15—C16	120.6 (2)	C13—C14—H14	119.5
C15—C16—C17	119.2 (2)	C15—C14—H14	119.5
C16—C17—C18	120.2 (2)	C14—C15—H15	119.7
C13—C18—C17	121.50 (17)	C16—C15—H15	119.7
C1—N2—H201	110.3	C15—C16—H16	120.4
C1—N2—H202	110.3	C17—C16—H16	120.4
C3—N2—H201	110.3	C16—C17—H17	119.9
C3—N2—H202	110.3	C18—C17—H17	119.9
H201—N2—H202	109.5	C13—C18—H18	119.2
N2—C1—H1	109.3	C17—C18—H18	119.2
C2—N1—C3—N2	−25.51 (14)	N2—C3—C6—C7	−85.03 (19)
C2—N1—C3—C5	−141.42 (12)	N2—C3—C6—C11	92.14 (17)
C2—N1—C3—C6	89.12 (15)	C5—C3—C6—C7	37.8 (2)
C3—N1—C2—O1	−171.77 (14)	C5—C3—C6—C11	−145.00 (16)
C3—N1—C2—C1	7.66 (16)	C3—C6—C7—C8	176.89 (16)
C4—N1—C2—O1	−2.7 (2)	C3—C6—C11—C10	−176.77 (16)
C4—N1—C2—C1	176.74 (13)	C7—C6—C11—C10	0.5 (2)
C4—N1—C3—N2	165.15 (13)	C11—C6—C7—C8	−0.4 (2)
C4—N1—C3—C5	49.24 (18)	C6—C7—C8—C9	−0.0 (2)
C4—N1—C3—C6	−80.22 (18)	C7—C8—C9—C10	0.3 (3)
C1—N2—C3—N1	33.21 (13)	C8—C9—C10—C11	−0.2 (3)
C1—N2—C3—C5	150.92 (13)	C9—C10—C11—C6	−0.2 (2)
C1—N2—C3—C6	−83.66 (14)	C1—C12—C13—C14	−179.68 (17)
C3—N2—C1—C2	−29.59 (13)	C1—C12—C13—C18	0.8 (2)
C3—N2—C1—C12	−151.10 (12)	C12—C13—C14—C15	−179.5 (2)
N2—C1—C2—O1	−166.51 (14)	C12—C13—C18—C17	178.83 (18)
N2—C1—C2—N1	14.06 (14)	C14—C13—C18—C17	−0.7 (2)
N2—C1—C12—C13	−81.41 (18)	C18—C13—C14—C15	0.1 (2)
C2—C1—C12—C13	163.27 (14)	C13—C14—C15—C16	0.5 (3)
C12—C1—C2—O1	−43.4 (2)	C14—C15—C16—C17	−0.5 (3)
C12—C1—C2—N1	137.17 (14)	C15—C16—C17—C18	−0.1 (2)
N1—C3—C6—C7	166.27 (15)	C16—C17—C18—C13	0.7 (3)
N1—C3—C6—C11	−16.6 (2)

D—H···A	D—H	H···A	D···A	D—H···A
N2—H201···Cl1	0.86	2.30	3.1170 (14)	160
N2—H202···Cl1i	0.86	2.24	3.0999 (14)	174

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N2—H201⋯Cl1	0.86	2.30	3.1170 (14)	160
N2—H202⋯Cl1i	0.86	2.24	3.0999 (14)	174

Symmetry code: (i) .