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

Zhang, S.; Wang, Y.; Li, B.; Zhang, G.; Luo, S.

doi:10.1107/S1600536809010460

organic compounds

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ISSN: 2056-9890

Volume 65| Part 4| April 2009| Page o888

doi:10.1107/S1600536809010460

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

Shuai Zhang,^a Yifeng Wang,^a Bailin Li,^a,^b Guangcun Zhang ^a and Shuping Luo ^a ^*

^aState Key Laboratory Breeding Base of Green Chemistry–Synthesis Technology, Zhejiang University of Technology, Hangzhou 310014, People's Republic of China, and ^bDepartment of Pharmaceutical and Chemical Engineering, Taizhou College, Linhai, Zhejiang 317000, People's Republic of China
^*Correspondence e-mail: shuaizhang867@gmail.com

(Received 18 February 2009; accepted 21 March 2009; online 28 March 2009)

The title hydrochloride salt, C₁₈H₂₁N₂O⁺·Cl⁻, is an imidazolidinone catalyst, which was derived from L-phenylalanine 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 supramolecular chains parallel to the crystallographic 2₁ screw axis are formed by N—H⋯Cl hydrogen bonds involving the NH₂⁺ and Cl⁻ groups. Intramolecular N—H⋯Cl interactions 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_r = 316.83
Monoclinic, P 2₁
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 F² > 2σ(F²)
R_int = 0.024

Refinement

R[F² > 2σ(F²)] = 0.030
wR(F²) = 0.073
S = 1.00
3371 reflections
201 parameters
H-atom parameters constrained
Δρ_max = 0.32 e Å⁻³
Δρ_min = −0.30 e Å⁻³
Absolute structure: Flack (1983 ), 1323 Friedel pairs
Flack parameter: 0.03 (4)

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) $[-x+2, y+{\script{1\over 2}}, -z+1]$ .

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.

Supporting information

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

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

checkCIF report

Comment top

Ten years ago, MacMillan and his laboratory developed chiral secondary amine catalysts based on the imidazolidinone architecture, which has led to the development of over 30 different enantioselective transformations for asymmetric synthesis (Ouellet et al., 2007). In recent years, Michael additions of aldehydes to enones with a MacMillan imidazolidinone catalyst have been reported (Hechavarria Fonseca & List, 2004). The title compound, prepared as a kind of organocatalyst for use in the asymmetric Michael addition of aldehydes to enones, was synthesized from L-phenylalanine. The crystal structure and absolute configuration of the title compound are reported in this article.

The compound consists of an ionic pair, a protonated ammonium cation and a Cl^- anion (Fig. 1). The chiral atom C1 has the expected S configuration, while the other chiral atom C3 was determined to be in a R configuration. The C1/C2/C3/N1 atoms of the imidazolidinone ring are almost coplanar. The distance of atom N2 to the C1/C2/C3/N1 mean plane is 0.497 (3) Å, while the distance of atom C12 of the benzyl group to the plane is 0.920 (4) Å. In the crystal structure of the title salt, one-dimensional supramolecular chains are formed, by intra- and inter-molecular N—H···Cl hydrogen bonds (Fig. 2).

Related literature top

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 top

To a stirred solution of L-phenylalanine (3.87 g, 24 mmol) in dry methanol (50 ml) was added thionyl chloride (2.72 ml, 37.5 mmol). After refluxed for 48 h., the solution was concentrated under vacuum and L-phenylalanine methyl ester dichloride crystallized from methanol to give white crystals. To an ethanolic MeNH₂ solution (8 M, 6 ml) was added L-phenylalanine methyl ester dihydrochloride (2.41 g, 10 mmol). The solution was stirred at room temperature for 24 h, and then the solvent removed under reduced pressure. To this residue was added MeOH (80 ml), acetophenone (3 g, 25 mmol), and a catalytic amount of p-toluenesulfonic acid (30 mg, 0.16 mmol). The resulting solution was refluxed for 24 h and further stirred at room temperature for 2 h. The mixture was subsequently concentrated under reduced pressure, giving the crude product. The resolution of the racemic compounds was by means of column chromatography with methyl and petroleum ether (1:4). The residue was taken up in ethylether and a solution of HCl-dioxane (4.0 M) was added to the precipitate. Suitable crystals were obtained by slow evaporation of a methanol solution of the crude at room temperature.

Computing details top

Data collection: PROCESS-AUTO (Rigaku, 1998); cell refinement: PROCESS-AUTO (Rigaku, 1998); 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 (Betteridge et al., 2003).

Figures top

	Fig. 1. The asymmetric unit of the title compound, with the atomic labelling scheme. Displacement ellipsoids are drawn at the 40% probability level.
	Fig. 2. A part of the crystal structure of the title salt, with hydrogen bonds represented with dashed lines.

(2R,5S)-5-Benzyl-2,3-dimethyl-4-oxo-2-phenylimidazolidin-1-ium chloride top

Crystal data top

C₁₈H₂₁N₂O⁺·Cl⁻	F(000) = 336.00
M_r = 316.83	D_x = 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

Data collection top

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

Refinement top

Refinement on F²	(Δ/σ)_max < 0.001
R[F² > 2σ(F²)] = 0.030	Δρ_max = 0.32 e Å⁻³
wR(F²) = 0.073	Δρ_min = −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	Absolute structure parameter: 0.03 (4)
w = 1/[0.0003F_o² + 1.04σ(F_o²)]/(4F_o²)

Crystal data top

C₁₈H₂₁N₂O⁺·Cl⁻	V = 841.10 (15) Å³
M_r = 316.83	Z = 2
Monoclinic, P2₁	Mo Kα radiation
a = 10.5797 (11) Å	µ = 0.23 mm⁻¹
b = 7.5876 (7) Å	T = 296 K
c = 10.8741 (12) Å	0.34 × 0.26 × 0.11 mm
β = 105.516 (3)°

Data collection top

Rigaku R-AXIS RAPID diffractometer	3371 independent reflections
Absorption correction: multi-scan (ABSCOR; Higashi, 1995)	2933 reflections with F² > 2σ(F²)
T_min = 0.920, T_max = 0.975	R_int = 0.024
8064 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.030	H-atom parameters constrained
wR(F²) = 0.073	Δρ_max = 0.32 e Å⁻³
S = 1.00	Δρ_min = −0.30 e Å⁻³
3371 reflections	Absolute structure: Flack (1983), 1323 Friedel pairs
201 parameters	Absolute structure parameter: 0.03 (4)

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å²) top

	x	y	z	U_iso*/U_eq
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*

Atomic displacement parameters (Å²) top

	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)

Geometric parameters (Å, º) top

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)

Hydrogen-bond geometry (Å, º) top

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) −x+2, y+1/2, −z+1.

Experimental details

Crystal data
Chemical formula	C₁₈H₂₁N₂O⁺·Cl⁻
M_r	316.83
Crystal system, space group	Monoclinic, P2₁
Temperature (K)	296
a, b, c (Å)	10.5797 (11), 7.5876 (7), 10.8741 (12)
β (°)	105.516 (3)
V (Å³)	841.10 (15)
Z	2
Radiation type	Mo Kα
µ (mm⁻¹)	0.23
Crystal size (mm)	0.34 × 0.26 × 0.11

Data collection
Diffractometer	Rigaku R-AXIS RAPID diffractometer
Absorption correction	Multi-scan (ABSCOR; Higashi, 1995)
T_min, T_max	0.920, 0.975
No. of measured, independent and observed [F² > 2σ(F²)] reflections	8064, 3371, 2933
R_int	0.024
(sin θ/λ)_max (Å⁻¹)	0.648

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.030, 0.073, 1.00
No. of reflections	3371
No. of parameters	201
No. of restraints	?
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.32, −0.30
Absolute structure	Flack (1983), 1323 Friedel pairs
Absolute structure parameter	0.03 (4)

Computer programs: PROCESS-AUTO (Rigaku, 1998), CrystalStructure (Rigaku/MSC, 2004), SIR97 (Altomare et al., 1999), CRYSTALS (Betteridge et al., 2003), ORTEPIII (Burnett & Johnson, 1996).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N2—H201···Cl1	0.860	2.297	3.1170 (14)	159.5
N2—H202···Cl1ⁱ	0.860	2.244	3.0999 (14)	174.1

Symmetry code: (i) −x+2, y+1/2, −z+1.

Acknowledgements

We thank Professor Jian-Ming Gu (Zhejiang University, China), for his help.

References

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