Ethyl trans-3-(2-chloro-6,7-dimethyl­quinolin-3-yl)-1-cyclo­hexyl­aziridine-2-carboxyl­ate

The molecule of the title compound, C₂₂H₂₇ClN₂O₂, contains a quinolyl unit linked to a functionalized aziridine system with a 2,3-trans arrangement of the substituents. The cyclo­hexyl ring adopts a chair conformation. The aziridine plane forms a dihedral angle of 51.23 (6)° with the 2-chloro­pyridine ring of the 2-chloro-6,7-dimethyl­quinolyl group. The mol­ecular structure is stabilized by intra­molecular C—H...O hydrogen bonds.

Key indicators

• Single-crystal X-ray study
• T = 100 K
• Mean [sigma](C-C)= 0.004 Å
• R factor = 0.049
• wR factor = 0.168
• Data-to-parameter ratio = 12.6

checkCIF/PLATON results

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Computing details

Data collection: COLLECT (Nonius, 1998); cell refinement: SCALEPACK (Otwinowski & Minor, 1997); data reduction: SCALEPACK and DENZO (Otwinowski & Minor, 1997); program(s) used to solve structure: SIR2002 (Burla et al., 2003); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEP-3 (Farrugia, 1997) and DIAMOND (Brandenburg & Berndt, 2001); software used to prepare material for publication: WinGX (Farrugia, 1999).

Ethyl trans-3-(2-chloro-6,7-dimethylquinolin-3-yl)-1- cyclohexylaziridine-2-carboxylate

Crystal data

C22H27ClN2O2	Z = 2
Mr = 386.91	F(000) = 412
Triclinic, P1	Dx = 1.269 Mg m^−3
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 9.8735 (8) Å	Cell parameters from 9080 reflections
b = 10.5870 (2) Å	θ = 1.9–26.4°
c = 11.5380 (2) Å	µ = 0.21 mm^−1
α = 68.421 (4)°	T = 100 K
β = 85.758 (4)°	Needle, colourless
γ = 65.125 (3)°	0.30 × 0.05 × 0.04 mm
V = 1012.83 (10) Å^3

Data collection

Nonius KappaCCD diffractometer	2618 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	Rint = 0.054
Graphite monochromator	θmax = 26.4°, θmin = 1.9°
φ scans, and ω scans with κ offsets	h = −9→12
9080 measured reflections	k = −13→13
4083 independent reflections	l = −14→13

Refinement

Refinement on F^2	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: difference Fourier map
R[F^2 > 2σ(F^2)] = 0.049	H-atom parameters constrained
wR(F^2) = 0.168	w = 1/[σ^2(Fo^2) + (0.0293P)^2 + 1.3984P] where P = (Fo^2 + 2Fc^2)/3
S = 1.02	(Δ/σ)max < 0.001
4083 reflections	Δρmax = 0.38 e Å^−3
325 parameters	Δρmin = −0.45 e Å^−3
0 restraints	Extinction correction: SHELXL97
Primary atom site location: structure-invariant direct methods	Extinction coefficient: none

Special details

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.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Ų)

	x	y	z	Uiso*/Ueq
Cl1	0.12439 (9)	0.87720 (8)	0.43586 (8)	0.0358 (2)
O2	−0.2198 (2)	0.7932 (2)	0.64558 (17)	0.0259 (5)
N2	0.0953 (2)	0.4584 (3)	0.6415 (2)	0.0189 (5)
N1	0.3105 (2)	0.7399 (3)	0.3042 (2)	0.0237 (5)
O1	−0.0184 (2)	0.6695 (2)	0.78655 (18)	0.0338 (5)
C13	0.1618 (3)	0.5650 (3)	0.6017 (2)	0.0209 (6)
H13	0.2082	0.5718	0.6701	0.025*
C10	0.4004 (3)	0.6155 (3)	0.2781 (2)	0.0200 (6)
C15	0.1159 (3)	0.3631 (3)	0.7751 (2)	0.0200 (6)
H15	0.1337	0.4126	0.8255	0.024*
C5	0.4152 (3)	0.4698 (3)	0.3539 (2)	0.0198 (6)
C7	0.5964 (3)	0.3656 (3)	0.2204 (3)	0.0229 (6)
C3	0.2430 (3)	0.5776 (3)	0.4872 (2)	0.0202 (6)
C2	0.2388 (3)	0.7175 (3)	0.4037 (3)	0.0236 (6)
C9	0.4827 (3)	0.6330 (3)	0.1723 (2)	0.0225 (6)
H9	0.4710	0.7288	0.1206	0.027*
C16	−0.0232 (3)	0.3355 (3)	0.8126 (2)	0.0240 (6)
H16A	−0.0461	0.2950	0.7576	0.029*
H16B	−0.1080	0.4298	0.8035	0.029*
C12	0.6687 (3)	0.5351 (3)	0.0316 (3)	0.0286 (7)
H12A	0.6418	0.6402	−0.0121	0.043*
H12B	0.6473	0.4951	−0.0235	0.043*
H12C	0.7738	0.4839	0.0594	0.043*
C17	0.0015 (3)	0.2262 (3)	0.9477 (3)	0.0280 (7)
H17A	−0.0865	0.2065	0.9687	0.034*
H17B	0.0150	0.2711	1.0031	0.034*
C14	−0.0054 (3)	0.6208 (3)	0.5977 (2)	0.0205 (6)
H14	−0.0598	0.6656	0.5146	0.025*
C18	0.1387 (3)	0.0786 (3)	0.9679 (3)	0.0278 (7)
H18A	0.1208	0.0283	0.9194	0.033*
H18B	0.1548	0.0138	1.0556	0.033*
C8	0.5790 (3)	0.5131 (3)	0.1438 (2)	0.0235 (6)
C22	−0.2986 (4)	0.8731 (3)	0.7270 (3)	0.0349 (8)
H22A	−0.2344	0.9054	0.7571	0.042*
H22B	−0.3261	0.8077	0.7988	0.042*
C4	0.3320 (3)	0.4549 (3)	0.4593 (2)	0.0202 (6)
H4	0.3378	0.3608	0.5100	0.024*
C20	0.2523 (3)	0.2164 (3)	0.7939 (3)	0.0227 (6)
H20A	0.3401	0.2364	0.7727	0.027*
H20B	0.2382	0.1725	0.7380	0.027*
C21	−0.0783 (3)	0.6940 (3)	0.6883 (3)	0.0251 (7)
C19	0.2787 (3)	0.1051 (3)	0.9289 (3)	0.0282 (7)
H19A	0.3039	0.1439	0.9842	0.034*
H19B	0.3624	0.0107	0.9363	0.034*
C11	0.7029 (3)	0.2319 (3)	0.1915 (3)	0.0316 (7)
H11A	0.7011	0.1423	0.2530	0.047*
H11B	0.8026	0.2258	0.1932	0.047*
H11C	0.6731	0.2424	0.1100	0.047*
C6	0.5132 (3)	0.3476 (3)	0.3221 (2)	0.0230 (6)
H6	0.5222	0.2518	0.3711	0.028*
C23	−0.4356 (3)	1.0056 (4)	0.6536 (3)	0.0433 (9)
H23A	−0.4887	1.0603	0.7055	0.065*
H23B	−0.4991	0.9725	0.6252	0.065*
H23C	−0.4074	1.0694	0.5827	0.065*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
Cl1	0.0391 (5)	0.0195 (4)	0.0487 (5)	−0.0108 (3)	0.0131 (4)	−0.0164 (4)
O2	0.0250 (11)	0.0224 (11)	0.0227 (11)	−0.0024 (9)	0.0050 (8)	−0.0098 (9)
N2	0.0191 (12)	0.0196 (13)	0.0179 (12)	−0.0070 (10)	0.0014 (9)	−0.0083 (10)
N1	0.0245 (13)	0.0201 (13)	0.0262 (13)	−0.0105 (11)	−0.0003 (10)	−0.0064 (11)
O1	0.0427 (13)	0.0266 (12)	0.0234 (11)	−0.0013 (10)	−0.0069 (10)	−0.0139 (10)
C13	0.0248 (15)	0.0187 (15)	0.0196 (14)	−0.0092 (13)	−0.0019 (11)	−0.0068 (12)
C10	0.0177 (14)	0.0192 (15)	0.0235 (15)	−0.0088 (12)	−0.0031 (11)	−0.0063 (12)
C15	0.0241 (15)	0.0197 (15)	0.0178 (14)	−0.0090 (12)	0.0019 (11)	−0.0093 (12)
C5	0.0185 (14)	0.0215 (15)	0.0192 (14)	−0.0075 (12)	−0.0018 (11)	−0.0078 (12)
C7	0.0209 (14)	0.0264 (16)	0.0237 (15)	−0.0101 (13)	0.0008 (12)	−0.0113 (13)
C3	0.0183 (14)	0.0205 (15)	0.0204 (14)	−0.0065 (12)	−0.0033 (11)	−0.0074 (12)
C2	0.0244 (15)	0.0175 (15)	0.0281 (16)	−0.0071 (12)	−0.0014 (12)	−0.0092 (13)
C9	0.0240 (15)	0.0209 (15)	0.0209 (15)	−0.0123 (13)	−0.0036 (11)	−0.0018 (12)
C16	0.0231 (15)	0.0287 (17)	0.0216 (15)	−0.0099 (13)	0.0049 (12)	−0.0125 (13)
C12	0.0298 (17)	0.0354 (18)	0.0253 (16)	−0.0188 (15)	0.0032 (13)	−0.0104 (14)
C17	0.0318 (17)	0.0317 (18)	0.0241 (16)	−0.0157 (14)	0.0082 (13)	−0.0126 (14)
C14	0.0235 (15)	0.0202 (15)	0.0163 (14)	−0.0055 (12)	0.0009 (11)	−0.0096 (12)
C18	0.0372 (17)	0.0227 (16)	0.0216 (15)	−0.0146 (14)	0.0041 (13)	−0.0044 (13)
C8	0.0232 (15)	0.0298 (17)	0.0199 (15)	−0.0155 (13)	−0.0013 (12)	−0.0063 (13)
C22	0.0421 (19)	0.0232 (17)	0.0297 (17)	−0.0060 (15)	0.0190 (14)	−0.0116 (14)
C4	0.0224 (15)	0.0183 (15)	0.0185 (14)	−0.0081 (12)	−0.0030 (11)	−0.0048 (12)
C20	0.0235 (15)	0.0210 (15)	0.0251 (15)	−0.0088 (13)	0.0042 (12)	−0.0113 (13)
C21	0.0306 (17)	0.0174 (15)	0.0237 (16)	−0.0055 (13)	0.0019 (13)	−0.0092 (13)
C19	0.0290 (16)	0.0221 (16)	0.0272 (16)	−0.0070 (14)	−0.0022 (13)	−0.0062 (13)
C11	0.0342 (18)	0.0302 (18)	0.0309 (17)	−0.0139 (15)	0.0112 (14)	−0.0130 (14)
C6	0.0270 (15)	0.0190 (15)	0.0230 (15)	−0.0105 (13)	0.0026 (12)	−0.0069 (12)
C23	0.0277 (18)	0.033 (2)	0.071 (3)	−0.0076 (15)	0.0126 (17)	−0.0293 (19)

Geometric parameters (Å, º)

Cl1—C2	1.751 (3)	C12—C8	1.515 (4)
O2—C21	1.336 (3)	C12—H12A	0.9600
O2—C22	1.458 (3)	C12—H12B	0.9600
N2—C13	1.453 (3)	C12—H12C	0.9600
N2—C15	1.472 (3)	C17—C18	1.526 (4)
N2—C14	1.482 (3)	C17—H17A	0.9700
N1—C2	1.303 (3)	C17—H17B	0.9700
N1—C10	1.372 (3)	C14—C21	1.492 (3)
O1—C21	1.206 (3)	C14—H14	0.9800
C13—C3	1.487 (4)	C18—C19	1.528 (4)
C13—C14	1.499 (4)	C18—H18A	0.9700
C13—H13	0.9800	C18—H18B	0.9700
C10—C9	1.413 (4)	C22—C23	1.487 (4)
C10—C5	1.415 (4)	C22—H22A	0.9700
C15—C20	1.519 (4)	C22—H22B	0.9700
C15—C16	1.522 (4)	C4—H4	0.9300
C15—H15	0.9800	C20—C19	1.527 (4)
C5—C6	1.411 (4)	C20—H20A	0.9700
C5—C4	1.413 (3)	C20—H20B	0.9700
C7—C6	1.383 (4)	C19—H19A	0.9700
C7—C8	1.426 (4)	C19—H19B	0.9700
C7—C11	1.504 (4)	C11—H11A	0.9600
C3—C4	1.367 (4)	C11—H11B	0.9600
C3—C2	1.424 (4)	C11—H11C	0.9600
C9—C8	1.367 (4)	C6—H6	0.9300
C9—H9	0.9300	C23—H23A	0.9600
C16—C17	1.524 (4)	C23—H23B	0.9600
C16—H16A	0.9700	C23—H23C	0.9600
C16—H16B	0.9700
C21—O2—C22	114.7 (2)	N2—C14—C13	58.34 (16)
C13—N2—C15	118.4 (2)	C21—C14—C13	115.7 (2)
C13—N2—C14	61.41 (18)	N2—C14—H14	116.3
C15—N2—C14	120.4 (2)	C21—C14—H14	116.3
C2—N1—C10	116.5 (2)	C13—C14—H14	116.3
N2—C13—C3	118.7 (2)	C17—C18—C19	111.2 (2)
N2—C13—C14	60.25 (17)	C17—C18—H18A	109.4
C3—C13—C14	122.8 (2)	C19—C18—H18A	109.4
N2—C13—H13	114.7	C17—C18—H18B	109.4
C3—C13—H13	114.7	C19—C18—H18B	109.4
C14—C13—H13	114.7	H18A—C18—H18B	108.0
N1—C10—C9	118.9 (2)	C9—C8—C7	119.9 (2)
N1—C10—C5	122.4 (2)	C9—C8—C12	120.7 (3)
C9—C10—C5	118.7 (2)	C7—C8—C12	119.4 (3)
N2—C15—C20	107.4 (2)	O2—C22—C23	108.2 (3)
N2—C15—C16	110.0 (2)	O2—C22—H22A	110.1
C20—C15—C16	110.8 (2)	C23—C22—H22A	110.1
N2—C15—H15	109.6	O2—C22—H22B	110.1
C20—C15—H15	109.6	C23—C22—H22B	110.1
C16—C15—H15	109.6	H22A—C22—H22B	108.4
C6—C5—C4	123.5 (3)	C3—C4—C5	120.5 (3)
C6—C5—C10	118.7 (2)	C3—C4—H4	119.8
C4—C5—C10	117.8 (2)	C5—C4—H4	119.8
C6—C7—C8	118.6 (3)	C15—C20—C19	111.7 (2)
C6—C7—C11	120.5 (3)	C15—C20—H20A	109.3
C8—C7—C11	120.8 (2)	C19—C20—H20A	109.3
C4—C3—C2	116.1 (2)	C15—C20—H20B	109.3
C4—C3—C13	122.0 (3)	C19—C20—H20B	109.3
C2—C3—C13	121.8 (2)	H20A—C20—H20B	107.9
N1—C2—C3	126.7 (3)	O1—C21—O2	123.8 (2)
N1—C2—Cl1	116.0 (2)	O1—C21—C14	125.2 (3)
C3—C2—Cl1	117.3 (2)	O2—C21—C14	111.0 (2)
C8—C9—C10	121.9 (3)	C20—C19—C18	110.6 (2)
C8—C9—H9	119.0	C20—C19—H19A	109.5
C10—C9—H9	119.0	C18—C19—H19A	109.5
C15—C16—C17	110.5 (2)	C20—C19—H19B	109.5
C15—C16—H16A	109.5	C18—C19—H19B	109.5
C17—C16—H16A	109.5	H19A—C19—H19B	108.1
C15—C16—H16B	109.5	C7—C11—H11A	109.5
C17—C16—H16B	109.5	C7—C11—H11B	109.5
H16A—C16—H16B	108.1	H11A—C11—H11B	109.5
C8—C12—H12A	109.5	C7—C11—H11C	109.5
C8—C12—H12B	109.5	H11A—C11—H11C	109.5
H12A—C12—H12B	109.5	H11B—C11—H11C	109.5
C8—C12—H12C	109.5	C7—C6—C5	122.1 (3)
H12A—C12—H12C	109.5	C7—C6—H6	119.0
H12B—C12—H12C	109.5	C5—C6—H6	119.0
C16—C17—C18	111.4 (2)	C22—C23—H23A	109.5
C16—C17—H17A	109.3	C22—C23—H23B	109.5
C18—C17—H17A	109.3	H23A—C23—H23B	109.5
C16—C17—H17B	109.3	C22—C23—H23C	109.5
C18—C17—H17B	109.3	H23A—C23—H23C	109.5
H17A—C17—H17B	108.0	H23B—C23—H23C	109.5
N2—C14—C21	121.1 (2)
C15—N2—C13—C3	135.3 (2)	C15—N2—C14—C13	108.0 (2)
C14—N2—C13—C3	−113.5 (3)	C3—C13—C14—N2	106.9 (3)
C15—N2—C13—C14	−111.2 (2)	N2—C13—C14—C21	112.2 (3)
C2—N1—C10—C9	−179.0 (2)	C3—C13—C14—C21	−141.0 (3)
C2—N1—C10—C5	0.3 (4)	C16—C17—C18—C19	55.8 (3)
C13—N2—C15—C20	−93.9 (3)	C10—C9—C8—C7	1.2 (4)
C14—N2—C15—C20	−165.7 (2)	C10—C9—C8—C12	−178.4 (2)
C13—N2—C15—C16	145.5 (2)	C6—C7—C8—C9	0.6 (4)
C14—N2—C15—C16	73.7 (3)	C11—C7—C8—C9	−179.3 (2)
N1—C10—C5—C6	−178.3 (2)	C6—C7—C8—C12	−179.7 (2)
C9—C10—C5—C6	1.0 (4)	C11—C7—C8—C12	0.3 (4)
N1—C10—C5—C4	0.7 (4)	C21—O2—C22—C23	164.7 (2)
C9—C10—C5—C4	180.0 (2)	C2—C3—C4—C5	0.9 (4)
N2—C13—C3—C4	−38.9 (4)	C13—C3—C4—C5	−175.9 (2)
C14—C13—C3—C4	−110.3 (3)	C6—C5—C4—C3	177.7 (2)
N2—C13—C3—C2	144.5 (3)	C10—C5—C4—C3	−1.3 (4)
C14—C13—C3—C2	73.1 (3)	N2—C15—C20—C19	−176.8 (2)
C10—N1—C2—C3	−0.7 (4)	C16—C15—C20—C19	−56.7 (3)
C10—N1—C2—Cl1	−179.98 (18)	C22—O2—C21—O1	0.6 (4)
C4—C3—C2—N1	0.1 (4)	C22—O2—C21—C14	−178.5 (2)
C13—C3—C2—N1	176.9 (3)	N2—C14—C21—O1	41.0 (4)
C4—C3—C2—Cl1	179.38 (19)	C13—C14—C21—O1	−26.1 (4)
C13—C3—C2—Cl1	−3.8 (4)	N2—C14—C21—O2	−139.9 (2)
N1—C10—C9—C8	177.3 (2)	C13—C14—C21—O2	153.1 (2)
C5—C10—C9—C8	−2.0 (4)	C15—C20—C19—C18	55.5 (3)
N2—C15—C16—C17	175.1 (2)	C17—C18—C19—C20	−54.7 (3)
C20—C15—C16—C17	56.6 (3)	C8—C7—C6—C5	−1.7 (4)
C15—C16—C17—C18	−56.5 (3)	C11—C7—C6—C5	178.3 (3)
C13—N2—C14—C21	−102.9 (3)	C4—C5—C6—C7	−178.1 (2)
C15—N2—C14—C21	5.1 (4)	C10—C5—C6—C7	0.9 (4)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
C13—H13···O1	0.98	2.55	2.908 (4)	101
C15—H15···O1	0.98	2.37	2.995 (4)	121