3-(4-Chloro-phen-yl)-7-methyl-4-(4-methyl-phen-yl)-1-oxa-2,7-diaza-spiro-[4.5]dec-2-en-10-one.

In the title compound, C(21)H(21)ClN(2)O(2), the dihydro-isoxazole ring adopts an envelope conformation and the piperidinone ring is in a chair conformation. The dihedral angle between the two benzene rings is 84.2 (1)°. The crystal used was an inversion twin.

Related literature

For general background, see: Diana et al. (1985 ▶); Huisgen (1984 ▶); Lepage et al. (1992 ▶); Ryng et al. (1998 ▶); Torssell (1988 ▶). For puckering parameters, see: Cremer & Pople (1975 ▶). For asymmetry parameters, see: Nardelli (1983 ▶).

Experimental

Crystal data

C21H21ClN2O2

M = 368.85

Orthorhombic,

a = 11.4585 (8) Å

b = 16.1132 (11) Å

c = 10.1038 (7) Å

V = 1865.5 (2) Å3

Z = 4

Mo Kα radiation

μ = 0.22 mm−1

T = 293 (2) K

0.24 × 0.23 × 0.20 mm

Data collection

Bruker SMART APEX CCD area-detector diffractometer

Absorption correction: none

16236 measured reflections

4350 independent reflections

3771 reflections with I > 2σ(I)

R int = 0.022

Refinement

R[F 2 > 2σ(F 2)] = 0.043

wR(F 2) = 0.111

S = 1.03

4350 reflections

238 parameters

H-atom parameters constrained

Δρmax = 0.24 e Å−3

Δρmin = −0.16 e Å−3

Absolute structure: Flack (1983 ▶), with 1846 Friedel pairs

Flack parameter: 0.65 (6)

Data collection: SMART (Bruker, 2001 ▶); cell refinement: SAINT (Bruker, 2001 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: PLATON (Spek, 2003 ▶); software used to prepare material for publication: SHELXL97 and PARST (Nardelli, 1995 ▶).

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536807068717/ci2543sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536807068717/ci2543Isup2.hkl

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

C21H21ClN2O2	F000 = 776
Mr = 368.85	Dx = 1.313 Mg m−3
Orthorhombic, P212121	Mo Kα radiation λ = 0.71073 Å
Hall symbol: P 2ac 2ab	Cell parameters from 2169 reflections
a = 11.4585 (8) Å	θ = 2.2–25.0º
b = 16.1132 (11) Å	µ = 0.22 mm−1
c = 10.1038 (7) Å	T = 293 (2) K
V = 1865.5 (2) Å3	Block, colourless
Z = 4	0.24 × 0.23 × 0.20 mm

Bruker SMART APEX CCD area-detector diffractometer	3771 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	Rint = 0.022
Monochromator: graphite	θmax = 28.0º
T = 293(2) K	θmin = 2.2º
ω scans	h = −14→14
Absorption correction: none	k = −20→20
16236 measured reflections	l = −12→13
4350 independent reflections

Refinement on F2	Hydrogen site location: inferred from neighbouring sites
Least-squares matrix: full	H-atom parameters constrained
R[F2 > 2σ(F2)] = 0.043	w = 1/[σ2(Fo2) + (0.0709P)2 + 0.0494P] where P = (Fo2 + 2Fc2)/3
wR(F2) = 0.111	(Δ/σ)max = 0.001
S = 1.04	Δρmax = 0.24 e Å−3
4350 reflections	Δρmin = −0.16 e Å−3
238 parameters	Extinction correction: none
Primary atom site location: structure-invariant direct methods	Absolute structure: Flack (1983); 1846 Friedel pairs
Secondary atom site location: difference Fourier map	Flack parameter: 0.65 (6)

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
C1	0.39999 (14)	0.21740 (10)	0.26025 (16)	0.0441 (4)
C2	0.47545 (14)	0.14014 (10)	0.28375 (16)	0.0432 (4)
H2	0.5027	0.1400	0.3757	0.052*
C3	0.57576 (15)	0.16160 (10)	0.19396 (17)	0.0451 (4)
C4	0.26874 (15)	0.20376 (11)	0.2506 (2)	0.0498 (4)
H4A	0.2523	0.1668	0.1771	0.060*
H4B	0.2414	0.1772	0.3310	0.060*
C5	0.2264 (2)	0.33753 (12)	0.3408 (2)	0.0643 (6)
H5A	0.2049	0.3109	0.4233	0.077*
H5B	0.1784	0.3866	0.3301	0.077*
C6	0.3552 (2)	0.36245 (12)	0.3452 (3)	0.0666 (6)
H6A	0.3773	0.3897	0.2633	0.080*
H6B	0.3691	0.4005	0.4179	0.080*
C7	0.42530 (17)	0.28489 (11)	0.36367 (19)	0.0516 (4)
C8	0.08128 (17)	0.26456 (16)	0.2160 (2)	0.0703 (6)
H8A	0.0523	0.2374	0.2939	0.106*
H8B	0.0692	0.2295	0.1405	0.106*
H8C	0.0404	0.3160	0.2035	0.106*
C9	0.42089 (13)	0.05732 (10)	0.25237 (16)	0.0422 (3)
C10	0.40319 (16)	0.03083 (11)	0.12336 (18)	0.0510 (4)
H10	0.4296	0.0634	0.0535	0.061*
C11	0.34703 (17)	−0.04313 (12)	0.0970 (2)	0.0567 (5)
H11	0.3365	−0.0596	0.0096	0.068*
C12	0.30606 (15)	−0.09324 (11)	0.1981 (2)	0.0535 (4)
C13	0.32650 (18)	−0.06790 (12)	0.3258 (2)	0.0590 (5)
H13	0.3018	−0.1012	0.3955	0.071*
C14	0.38319 (16)	0.00627 (11)	0.35339 (18)	0.0520 (4)
H14	0.3959	0.0217	0.4409	0.062*
C15	0.2395 (2)	−0.17151 (13)	0.1691 (3)	0.0755 (7)
H15A	0.2165	−0.1972	0.2507	0.113*
H15B	0.2882	−0.2090	0.1199	0.113*
H15C	0.1713	−0.1584	0.1180	0.113*
C16	0.69030 (15)	0.12007 (10)	0.19526 (18)	0.0453 (4)
C17	0.77102 (16)	0.13329 (12)	0.09496 (19)	0.0522 (4)
H17	0.7506	0.1654	0.0221	0.063*
C18	0.88106 (17)	0.09925 (12)	0.1024 (2)	0.0559 (4)
H18	0.9347	0.1079	0.0347	0.067*
C19	0.91083 (15)	0.05239 (11)	0.2108 (2)	0.0526 (4)
C20	0.83202 (17)	0.03571 (11)	0.30978 (19)	0.0559 (5)
H20	0.8526	0.0022	0.3810	0.067*
C21	0.72139 (17)	0.06986 (12)	0.30132 (19)	0.0527 (4)
H21	0.6671	0.0590	0.3676	0.063*
N1	0.55545 (14)	0.22078 (9)	0.11384 (15)	0.0530 (4)
N2	0.20607 (14)	0.28110 (9)	0.23159 (16)	0.0548 (4)
O1	0.44115 (11)	0.25059 (8)	0.13460 (12)	0.0552 (3)
O2	0.49219 (14)	0.27449 (9)	0.45270 (15)	0.0714 (4)
Cl1	1.05097 (4)	0.01181 (4)	0.22360 (6)	0.07411 (18)

	U11	U22	U33	U12	U13	U23
C1	0.0457 (8)	0.0424 (8)	0.0441 (9)	0.0017 (7)	0.0011 (7)	0.0028 (6)
C2	0.0438 (8)	0.0449 (8)	0.0410 (8)	0.0035 (6)	−0.0025 (7)	0.0023 (7)
C3	0.0428 (8)	0.0451 (8)	0.0476 (9)	−0.0007 (7)	−0.0009 (7)	−0.0016 (7)
C4	0.0457 (8)	0.0503 (9)	0.0532 (10)	0.0026 (7)	−0.0022 (8)	0.0016 (8)
C5	0.0689 (13)	0.0495 (10)	0.0744 (14)	0.0179 (9)	0.0117 (11)	0.0037 (9)
C6	0.0768 (14)	0.0425 (9)	0.0805 (14)	0.0026 (9)	0.0013 (12)	−0.0085 (9)
C7	0.0498 (10)	0.0469 (9)	0.0580 (10)	−0.0047 (7)	0.0042 (9)	0.0014 (8)
C8	0.0503 (10)	0.0856 (14)	0.0751 (13)	0.0143 (10)	0.0057 (10)	0.0159 (12)
C9	0.0379 (7)	0.0420 (8)	0.0467 (9)	0.0046 (6)	0.0004 (7)	0.0029 (6)
C10	0.0549 (10)	0.0498 (9)	0.0482 (9)	0.0000 (8)	0.0031 (8)	0.0028 (7)
C11	0.0554 (10)	0.0553 (11)	0.0595 (11)	0.0033 (8)	−0.0044 (9)	−0.0067 (9)
C12	0.0407 (8)	0.0428 (9)	0.0769 (13)	0.0073 (7)	−0.0018 (9)	−0.0003 (8)
C13	0.0582 (11)	0.0477 (9)	0.0710 (13)	0.0022 (9)	0.0080 (9)	0.0151 (9)
C14	0.0563 (10)	0.0509 (9)	0.0489 (9)	0.0031 (8)	0.0013 (8)	0.0037 (8)
C15	0.0590 (12)	0.0509 (11)	0.116 (2)	−0.0032 (9)	−0.0063 (13)	−0.0041 (12)
C16	0.0425 (8)	0.0422 (8)	0.0510 (9)	−0.0008 (7)	−0.0021 (7)	−0.0060 (7)
C17	0.0485 (9)	0.0548 (10)	0.0534 (10)	0.0006 (8)	0.0014 (8)	0.0024 (8)
C18	0.0465 (9)	0.0619 (11)	0.0594 (11)	0.0015 (8)	0.0070 (9)	−0.0020 (9)
C19	0.0428 (8)	0.0517 (9)	0.0634 (11)	0.0056 (7)	−0.0035 (8)	−0.0114 (8)
C20	0.0586 (11)	0.0551 (10)	0.0541 (10)	0.0111 (8)	−0.0027 (9)	0.0004 (8)
C21	0.0505 (9)	0.0547 (10)	0.0527 (10)	0.0035 (8)	0.0059 (8)	0.0000 (8)
N1	0.0471 (8)	0.0580 (9)	0.0540 (8)	0.0063 (7)	0.0061 (7)	0.0053 (7)
N2	0.0495 (8)	0.0569 (9)	0.0580 (9)	0.0087 (7)	0.0036 (7)	0.0104 (7)
O1	0.0519 (7)	0.0619 (7)	0.0519 (6)	0.0132 (6)	0.0056 (6)	0.0146 (6)
O2	0.0826 (11)	0.0639 (9)	0.0678 (9)	−0.0015 (8)	−0.0190 (8)	−0.0105 (7)
Cl1	0.0503 (3)	0.0879 (4)	0.0841 (4)	0.0210 (2)	−0.0020 (2)	−0.0061 (3)

C1—O1	1.456 (2)	C9—C10	1.386 (2)
C1—C4	1.523 (2)	C10—C11	1.380 (3)
C1—C2	1.534 (2)	C10—H10	0.93
C1—C7	1.536 (2)	C11—C12	1.384 (3)
C2—C3	1.505 (2)	C11—H11	0.93
C2—C9	1.507 (2)	C12—C13	1.374 (3)
C2—H2	0.98	C12—C15	1.503 (3)
C3—N1	1.272 (2)	C13—C14	1.389 (3)
C3—C16	1.473 (2)	C13—H13	0.93
C4—N2	1.451 (2)	C14—H14	0.93
C4—H4A	0.97	C15—H15A	0.96
C4—H4B	0.97	C15—H15B	0.96
C5—N2	1.448 (3)	C15—H15C	0.96
C5—C6	1.530 (3)	C16—C17	1.388 (3)
C5—H5A	0.97	C16—C21	1.389 (3)
C5—H5B	0.97	C17—C18	1.377 (3)
C6—C7	1.497 (3)	C17—H17	0.93
C6—H6A	0.97	C18—C19	1.373 (3)
C6—H6B	0.97	C18—H18	0.93
C7—O2	1.194 (2)	C19—C20	1.374 (3)
C8—N2	1.463 (3)	C19—Cl1	1.7386 (17)
C8—H8A	0.96	C20—C21	1.385 (3)
C8—H8B	0.96	C20—H20	0.93
C8—H8C	0.96	C21—H21	0.93
C9—C14	1.380 (2)	N1—O1	1.411 (2)
O1—C1—C4	108.48 (14)	C11—C10—C9	121.03 (17)
O1—C1—C2	104.50 (13)	C11—C10—H10	119.5
C4—C1—C2	116.71 (14)	C9—C10—H10	119.5
O1—C1—C7	105.78 (13)	C10—C11—C12	121.29 (19)
C4—C1—C7	109.40 (14)	C10—C11—H11	119.4
C2—C1—C7	111.27 (14)	C12—C11—H11	119.4
C3—C2—C9	113.17 (14)	C13—C12—C11	117.52 (17)
C3—C2—C1	98.68 (13)	C13—C12—C15	121.3 (2)
C9—C2—C1	116.88 (13)	C11—C12—C15	121.2 (2)
C3—C2—H2	109.2	C12—C13—C14	121.60 (18)
C9—C2—H2	109.2	C12—C13—H13	119.2
C1—C2—H2	109.2	C14—C13—H13	119.2
N1—C3—C16	120.60 (16)	C9—C14—C13	120.73 (17)
N1—C3—C2	114.59 (15)	C9—C14—H14	119.6
C16—C3—C2	124.81 (14)	C13—C14—H14	119.6
N2—C4—C1	111.92 (15)	C12—C15—H15A	109.5
N2—C4—H4A	109.2	C12—C15—H15B	109.5
C1—C4—H4A	109.2	H15A—C15—H15B	109.5
N2—C4—H4B	109.2	C12—C15—H15C	109.5
C1—C4—H4B	109.2	H15A—C15—H15C	109.5
H4A—C4—H4B	107.9	H15B—C15—H15C	109.5
N2—C5—C6	110.03 (17)	C17—C16—C21	118.79 (16)
N2—C5—H5A	109.7	C17—C16—C3	121.15 (16)
C6—C5—H5A	109.7	C21—C16—C3	119.99 (16)
N2—C5—H5B	109.7	C18—C17—C16	120.60 (18)
C6—C5—H5B	109.7	C18—C17—H17	119.7
H5A—C5—H5B	108.2	C16—C17—H17	119.7
C7—C6—C5	107.56 (16)	C19—C18—C17	119.33 (18)
C7—C6—H6A	110.2	C19—C18—H18	120.3
C5—C6—H6A	110.2	C17—C18—H18	120.3
C7—C6—H6B	110.2	C18—C19—C20	121.66 (16)
C5—C6—H6B	110.2	C18—C19—Cl1	119.72 (15)
H6A—C6—H6B	108.5	C20—C19—Cl1	118.62 (15)
O2—C7—C6	123.75 (19)	C19—C20—C21	118.62 (17)
O2—C7—C1	122.32 (16)	C19—C20—H20	120.7
C6—C7—C1	113.88 (17)	C21—C20—H20	120.7
N2—C8—H8A	109.5	C20—C21—C16	120.92 (17)
N2—C8—H8B	109.5	C20—C21—H21	119.5
H8A—C8—H8B	109.5	C16—C21—H21	119.5
N2—C8—H8C	109.5	C3—N1—O1	109.30 (14)
H8A—C8—H8C	109.5	C5—N2—C4	111.01 (15)
H8B—C8—H8C	109.5	C5—N2—C8	110.72 (16)
C14—C9—C10	117.78 (16)	C4—N2—C8	109.97 (16)
C14—C9—C2	120.12 (15)	N1—O1—C1	107.77 (12)
C10—C9—C2	122.07 (15)
O1—C1—C2—C3	20.69 (15)	C10—C11—C12—C15	176.79 (18)
C4—C1—C2—C3	140.47 (15)	C11—C12—C13—C14	1.8 (3)
C7—C1—C2—C3	−93.02 (15)	C15—C12—C13—C14	−176.97 (18)
O1—C1—C2—C9	−100.88 (16)	C10—C9—C14—C13	−1.8 (3)
C4—C1—C2—C9	18.9 (2)	C2—C9—C14—C13	176.12 (16)
C7—C1—C2—C9	145.41 (15)	C12—C13—C14—C9	0.1 (3)
C9—C2—C3—N1	110.31 (17)	N1—C3—C16—C17	−11.9 (3)
C1—C2—C3—N1	−13.93 (19)	C2—C3—C16—C17	168.66 (16)
C9—C2—C3—C16	−70.2 (2)	N1—C3—C16—C21	164.90 (17)
C1—C2—C3—C16	165.53 (15)	C2—C3—C16—C21	−14.5 (3)
O1—C1—C4—N2	−63.77 (19)	C21—C16—C17—C18	−1.9 (3)
C2—C1—C4—N2	178.61 (15)	C3—C16—C17—C18	174.95 (17)
C7—C1—C4—N2	51.2 (2)	C16—C17—C18—C19	−0.5 (3)
N2—C5—C6—C7	−60.1 (2)	C17—C18—C19—C20	2.7 (3)
C5—C6—C7—O2	−123.4 (2)	C17—C18—C19—Cl1	−178.00 (15)
C5—C6—C7—C1	54.2 (2)	C18—C19—C20—C21	−2.4 (3)
O1—C1—C7—O2	−115.9 (2)	Cl1—C19—C20—C21	178.29 (14)
C4—C1—C7—O2	127.43 (19)	C19—C20—C21—C16	−0.1 (3)
C2—C1—C7—O2	−3.0 (2)	C17—C16—C21—C20	2.2 (3)
O1—C1—C7—C6	66.42 (19)	C3—C16—C21—C20	−174.70 (17)
C4—C1—C7—C6	−50.2 (2)	C16—C3—N1—O1	−178.78 (14)
C2—C1—C7—C6	179.33 (16)	C2—C3—N1—O1	0.7 (2)
C3—C2—C9—C14	141.75 (16)	C6—C5—N2—C4	64.4 (2)
C1—C2—C9—C14	−104.61 (18)	C6—C5—N2—C8	−173.13 (17)
C3—C2—C9—C10	−40.4 (2)	C1—C4—N2—C5	−60.1 (2)
C1—C2—C9—C10	73.2 (2)	C1—C4—N2—C8	177.08 (16)
C14—C9—C10—C11	1.6 (3)	C3—N1—O1—C1	14.11 (18)
C2—C9—C10—C11	−176.26 (16)	C4—C1—O1—N1	−147.46 (14)
C9—C10—C11—C12	0.3 (3)	C2—C1—O1—N1	−22.29 (16)
C10—C11—C12—C13	−2.0 (3)	C7—C1—O1—N1	95.25 (15)