r-2,c-6-Bis­(2-chloro­phen­yl)-t-3,t-5-dimethyl-1-nitrosopiperidin-4-one oxime

In the title compound, C₁₉H₁₉Cl₂N₃O₂, the piperidine ring adopts a distorted boat conformation. In the solid state, the mol­ecules exist as O—H...N-hydrogen-bonded centrosymmetric dimers.

Key indicators

• Single-crystal X-ray study
• T = 273 K
• Mean [sigma](C-C)= 0.003 Å
• R factor = 0.038
• wR factor = 0.101
• Data-to-parameter ratio = 13.9

checkCIF/PLATON results

No syntax errors found


No errors found in this datablock

checkCIF publication errors

Alert level A
PUBL024_ALERT_1_A The number of authors is greater than 5.
              Please specify the role of each of the co-authors
              for your paper.

   1 ALERT level A = Data missing that is essential or data in wrong format
   0 ALERT level G = General alerts. Data that may be required is missing

---

Computing details

Data collection: SMART (Bruker, 2001); cell refinement: SAINT (Bruker, 2001); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEP-3 (Farrugia, 1997); software used to prepare material for publication: SHELXL97.

t(3),t(5)-Dimethyl N-nitroso-r(2),c(6)-bis(o-chlorophenyl)piperidine-4-one oxime.

Crystal data

C19H19Cl2N3O2	Z = 2
Mr = 392.27	F(000) = 408
Triclinic, P1	Dx = 1.385 Mg m^−3
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 7.9168 (7) Å	Cell parameters from 6230 reflections
b = 8.5941 (8) Å	θ = 2.4–28.0°
c = 14.1572 (13) Å	µ = 0.36 mm^−1
α = 90.225 (2)°	T = 273 K
β = 101.459 (2)°	Block, colourless
γ = 94.810 (2)°	0.20 × 0.18 × 0.18 mm
V = 940.49 (15) Å^3

Data collection

Bruker SMART APEX CCD area-detector diffractometer	3062 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	Rint = 0.015
Graphite monochromator	θmax = 25.0°, θmin = 2.4°
ω scan	h = −9→9
9029 measured reflections	k = −10→10
3313 independent reflections	l = −16→16

Refinement

Refinement on F^2	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F^2 > 2σ(F^2)] = 0.038	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.101	H-atom parameters constrained
S = 1.04	w = 1/[σ^2(Fo^2) + (0.0478P)^2 + 0.427P] where P = (Fo^2 + 2Fc^2)/3
3313 reflections	(Δ/σ)max = 0.001
238 parameters	Δρmax = 0.41 e Å^−3
0 restraints	Δρmin = −0.21 e Å^−3

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	−0.28911 (7)	0.69334 (7)	0.05545 (4)	0.06533 (19)
Cl2	0.17287 (8)	0.87254 (7)	0.50968 (4)	0.06339 (18)
N1	0.09785 (17)	0.91367 (16)	0.27903 (10)	0.0348 (3)
N21	−0.0258 (2)	0.99265 (18)	0.30342 (12)	0.0468 (4)
N23	0.40854 (19)	0.96741 (17)	0.08402 (11)	0.0407 (3)
O22	−0.17098 (18)	0.95549 (18)	0.25574 (12)	0.0586 (4)
O24	0.51706 (18)	1.10777 (15)	0.09550 (10)	0.0504 (3)
H24	0.5727	1.1137	0.0524	0.060*
C2	0.2749 (2)	0.97996 (19)	0.32025 (12)	0.0365 (4)
H2	0.2634	1.0651	0.3642	0.044*
C3	0.3496 (2)	1.0565 (2)	0.23774 (13)	0.0394 (4)
H3	0.4728	1.0870	0.2616	0.047*
C4	0.3320 (2)	0.9430 (2)	0.15440 (12)	0.0374 (4)
C5	0.2229 (2)	0.7894 (2)	0.15403 (13)	0.0416 (4)
H5	0.2911	0.7221	0.1997	0.050*
C6	0.0567 (2)	0.81217 (19)	0.19219 (12)	0.0354 (4)
H6	−0.0218	0.8646	0.1424	0.043*
C7	0.1824 (3)	0.7036 (3)	0.05703 (17)	0.0679 (7)
H71	0.1186	0.7673	0.0095	0.102*
H72	0.1147	0.6071	0.0619	0.102*
H73	0.2885	0.6823	0.0384	0.102*
C8	0.2589 (3)	1.2033 (2)	0.20598 (16)	0.0559 (5)
H81	0.3077	1.2517	0.1554	0.084*
H82	0.2743	1.2751	0.2598	0.084*
H83	0.1376	1.1754	0.1829	0.084*
C9	−0.0362 (2)	0.65809 (19)	0.21299 (12)	0.0355 (4)
C10	−0.1899 (2)	0.5945 (2)	0.15543 (13)	0.0424 (4)
C11	−0.2689 (3)	0.4517 (2)	0.17451 (15)	0.0506 (5)
H11	−0.3714	0.4121	0.1346	0.061*
C12	−0.1959 (3)	0.3688 (2)	0.25217 (16)	0.0536 (5)
H12	−0.2480	0.2722	0.2648	0.064*
C13	−0.0451 (3)	0.4290 (2)	0.31155 (16)	0.0527 (5)
H13	0.0042	0.3738	0.3649	0.063*
C14	0.0330 (2)	0.5720 (2)	0.29161 (14)	0.0441 (4)
H14	0.1349	0.6114	0.3322	0.053*
C15	0.3865 (2)	0.8666 (2)	0.38052 (13)	0.0400 (4)
C16	0.5340 (2)	0.8172 (2)	0.35496 (16)	0.0538 (5)
H16	0.5616	0.8486	0.2967	0.065*
C17	0.6409 (3)	0.7227 (3)	0.4135 (2)	0.0676 (6)
H17	0.7390	0.6914	0.3945	0.081*
C18	0.6025 (3)	0.6753 (3)	0.49956 (19)	0.0690 (7)
H18	0.6748	0.6120	0.5392	0.083*
C19	0.4573 (3)	0.7211 (3)	0.52759 (16)	0.0599 (6)
H19	0.4305	0.6883	0.5858	0.072*
C20	0.3518 (3)	0.8157 (2)	0.46886 (13)	0.0462 (4)

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
Cl1	0.0584 (3)	0.0712 (4)	0.0560 (3)	−0.0062 (3)	−0.0090 (2)	0.0103 (3)
Cl2	0.0880 (4)	0.0645 (3)	0.0476 (3)	0.0076 (3)	0.0368 (3)	0.0055 (2)
N1	0.0349 (7)	0.0341 (7)	0.0388 (8)	−0.0011 (6)	0.0171 (6)	−0.0017 (6)
N21	0.0456 (9)	0.0451 (9)	0.0564 (10)	0.0044 (7)	0.0264 (8)	0.0024 (7)
N23	0.0432 (8)	0.0393 (8)	0.0431 (8)	−0.0063 (6)	0.0210 (7)	−0.0001 (6)
O22	0.0386 (8)	0.0654 (9)	0.0761 (10)	0.0059 (7)	0.0214 (7)	0.0024 (8)
O24	0.0551 (8)	0.0486 (7)	0.0514 (8)	−0.0128 (6)	0.0273 (6)	0.0007 (6)
C2	0.0397 (9)	0.0344 (9)	0.0376 (9)	−0.0065 (7)	0.0174 (7)	−0.0037 (7)
C3	0.0429 (9)	0.0367 (9)	0.0414 (9)	−0.0070 (7)	0.0192 (8)	−0.0010 (7)
C4	0.0393 (9)	0.0378 (9)	0.0388 (9)	−0.0008 (7)	0.0181 (7)	0.0010 (7)
C5	0.0479 (10)	0.0365 (9)	0.0449 (10)	−0.0055 (7)	0.0240 (8)	−0.0052 (7)
C6	0.0373 (9)	0.0350 (9)	0.0345 (8)	−0.0031 (7)	0.0110 (7)	0.0008 (7)
C7	0.0775 (15)	0.0656 (14)	0.0657 (14)	−0.0243 (12)	0.0399 (12)	−0.0251 (11)
C8	0.0788 (15)	0.0410 (10)	0.0561 (12)	0.0036 (10)	0.0340 (11)	0.0048 (9)
C9	0.0346 (8)	0.0346 (8)	0.0390 (9)	−0.0011 (7)	0.0135 (7)	−0.0010 (7)
C10	0.0400 (9)	0.0445 (10)	0.0426 (10)	−0.0020 (8)	0.0108 (8)	−0.0008 (8)
C11	0.0430 (10)	0.0492 (11)	0.0579 (12)	−0.0126 (8)	0.0130 (9)	−0.0081 (9)
C12	0.0567 (12)	0.0377 (10)	0.0687 (13)	−0.0105 (9)	0.0244 (10)	0.0024 (9)
C13	0.0556 (12)	0.0433 (11)	0.0598 (12)	0.0004 (9)	0.0143 (10)	0.0143 (9)
C14	0.0403 (10)	0.0420 (10)	0.0481 (10)	−0.0034 (8)	0.0071 (8)	0.0045 (8)
C15	0.0378 (9)	0.0390 (9)	0.0409 (9)	−0.0098 (7)	0.0083 (7)	−0.0040 (7)
C16	0.0403 (10)	0.0576 (12)	0.0632 (13)	−0.0048 (9)	0.0135 (9)	0.0029 (10)
C17	0.0416 (11)	0.0643 (14)	0.0942 (19)	0.0041 (10)	0.0071 (11)	0.0032 (13)
C18	0.0662 (15)	0.0539 (13)	0.0746 (16)	−0.0002 (11)	−0.0129 (12)	0.0056 (11)
C19	0.0758 (15)	0.0504 (12)	0.0468 (11)	−0.0050 (11)	0.0004 (10)	0.0032 (9)
C20	0.0551 (11)	0.0410 (10)	0.0404 (10)	−0.0078 (8)	0.0099 (8)	−0.0044 (8)

Geometric parameters (Å, º)

Cl1—C10	1.738 (2)	C8—H81	0.96
Cl2—C20	1.738 (2)	C8—H82	0.96
N1—N21	1.335 (2)	C8—H83	0.96
N1—C6	1.471 (2)	C9—C14	1.385 (3)
N1—C2	1.472 (2)	C9—C10	1.391 (2)
N21—O22	1.228 (2)	C10—C11	1.382 (3)
N23—C4	1.274 (2)	C11—C12	1.369 (3)
N23—O24	1.4102 (19)	C11—H11	0.93
O24—H24	0.82	C12—C13	1.376 (3)
C2—C15	1.520 (3)	C12—H12	0.93
C2—C3	1.537 (2)	C13—C14	1.384 (3)
C2—H2	0.98	C13—H13	0.93
C3—C4	1.505 (2)	C14—H14	0.93
C3—C8	1.530 (3)	C15—C16	1.387 (3)
C3—H3	0.98	C15—C20	1.397 (3)
C4—C5	1.515 (2)	C16—C17	1.380 (3)
C5—C7	1.520 (3)	C16—H16	0.93
C5—C6	1.545 (2)	C17—C18	1.369 (4)
C5—H5	0.98	C17—H17	0.93
C6—C9	1.519 (2)	C18—C19	1.375 (4)
C6—H6	0.98	C18—H18	0.93
C7—H71	0.96	C19—C20	1.376 (3)
C7—H72	0.96	C19—H19	0.93
C7—H73	0.96
N21—N1—C6	119.37 (14)	H81—C8—H82	109.5
N21—N1—C2	114.06 (13)	C3—C8—H83	109.5
C6—N1—C2	122.65 (13)	H81—C8—H83	109.5
O22—N21—N1	113.91 (15)	H82—C8—H83	109.5
C4—N23—O24	112.59 (14)	C14—C9—C10	116.56 (16)
N23—O24—H24	109.5	C14—C9—C6	120.19 (15)
N1—C2—C15	114.12 (13)	C10—C9—C6	123.24 (16)
N1—C2—C3	107.33 (14)	C11—C10—C9	121.98 (18)
C15—C2—C3	115.80 (14)	C11—C10—Cl1	117.54 (15)
N1—C2—H2	106.3	C9—C10—Cl1	120.48 (14)
C15—C2—H2	106.3	C12—C11—C10	119.93 (18)
C3—C2—H2	106.3	C12—C11—H11	120.0
C4—C3—C8	110.89 (16)	C10—C11—H11	120.0
C4—C3—C2	110.65 (14)	C11—C12—C13	119.74 (17)
C8—C3—C2	109.90 (15)	C11—C12—H12	120.1
C4—C3—H3	108.4	C13—C12—H12	120.1
C8—C3—H3	108.4	C12—C13—C14	119.80 (19)
C2—C3—H3	108.4	C12—C13—H13	120.1
N23—C4—C3	123.20 (15)	C14—C13—H13	120.1
N23—C4—C5	117.39 (15)	C13—C14—C9	121.99 (18)
C3—C4—C5	119.38 (14)	C13—C14—H14	119.0
C4—C5—C7	113.69 (15)	C9—C14—H14	119.0
C4—C5—C6	110.99 (14)	C16—C15—C20	116.42 (18)
C7—C5—C6	111.55 (16)	C16—C15—C2	122.41 (16)
C4—C5—H5	106.7	C20—C15—C2	121.02 (16)
C7—C5—H5	106.7	C17—C16—C15	121.9 (2)
C6—C5—H5	106.7	C17—C16—H16	119.0
N1—C6—C9	110.35 (13)	C15—C16—H16	119.0
N1—C6—C5	110.09 (13)	C18—C17—C16	119.9 (2)
C9—C6—C5	112.35 (14)	C18—C17—H17	120.1
N1—C6—H6	108.0	C16—C17—H17	120.1
C9—C6—H6	108.0	C17—C18—C19	120.1 (2)
C5—C6—H6	108.0	C17—C18—H18	119.9
C5—C7—H71	109.5	C19—C18—H18	119.9
C5—C7—H72	109.5	C18—C19—C20	119.5 (2)
H71—C7—H72	109.5	C18—C19—H19	120.2
C5—C7—H73	109.5	C20—C19—H19	120.2
H71—C7—H73	109.5	C19—C20—C15	122.1 (2)
H72—C7—H73	109.5	C19—C20—Cl2	117.17 (16)
C3—C8—H81	109.5	C15—C20—Cl2	120.70 (16)
C3—C8—H82	109.5
C6—N1—N21—O22	9.0 (2)	C5—C6—C9—C14	71.9 (2)
C2—N1—N21—O22	167.34 (15)	N1—C6—C9—C10	129.75 (17)
N21—N1—C2—C15	122.96 (16)	C5—C6—C9—C10	−106.98 (19)
C6—N1—C2—C15	−79.50 (19)	C14—C9—C10—C11	−0.9 (3)
N21—N1—C2—C3	−107.32 (16)	C6—C9—C10—C11	178.03 (17)
C6—N1—C2—C3	50.23 (19)	C14—C9—C10—Cl1	179.47 (14)
N1—C2—C3—C4	−52.63 (18)	C6—C9—C10—Cl1	−1.6 (2)
C15—C2—C3—C4	76.14 (19)	C9—C10—C11—C12	0.2 (3)
N1—C2—C3—C8	70.18 (18)	Cl1—C10—C11—C12	179.81 (16)
C15—C2—C3—C8	−161.05 (15)	C10—C11—C12—C13	0.7 (3)
O24—N23—C4—C3	2.9 (2)	C11—C12—C13—C14	−0.9 (3)
O24—N23—C4—C5	−175.24 (15)	C12—C13—C14—C9	0.1 (3)
C8—C3—C4—N23	69.9 (2)	C10—C9—C14—C13	0.8 (3)
C2—C3—C4—N23	−167.89 (17)	C6—C9—C14—C13	−178.20 (17)
C8—C3—C4—C5	−111.99 (18)	N1—C2—C15—C16	116.29 (18)
C2—C3—C4—C5	10.2 (2)	C3—C2—C15—C16	−9.1 (2)
N23—C4—C5—C7	−15.1 (3)	N1—C2—C15—C20	−68.5 (2)
C3—C4—C5—C7	166.72 (19)	C3—C2—C15—C20	166.17 (16)
N23—C4—C5—C6	−141.78 (17)	C20—C15—C16—C17	0.0 (3)
C3—C4—C5—C6	40.0 (2)	C2—C15—C16—C17	175.47 (19)
N21—N1—C6—C9	−79.21 (18)	C15—C16—C17—C18	0.0 (3)
C2—N1—C6—C9	124.39 (16)	C16—C17—C18—C19	0.3 (4)
N21—N1—C6—C5	156.22 (15)	C17—C18—C19—C20	−0.5 (3)
C2—N1—C6—C5	−0.2 (2)	C18—C19—C20—C15	0.5 (3)
C4—C5—C6—N1	−44.38 (19)	C18—C19—C20—Cl2	−178.71 (17)
C7—C5—C6—N1	−172.28 (17)	C16—C15—C20—C19	−0.3 (3)
C4—C5—C6—C9	−167.79 (15)	C2—C15—C20—C19	−175.78 (17)
C7—C5—C6—C9	64.3 (2)	C16—C15—C20—Cl2	178.92 (14)
N1—C6—C9—C14	−51.3 (2)	C2—C15—C20—Cl2	3.4 (2)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
O24—H24···N23^i	0.82	2.09	2.8052 (19)	146

Symmetry code: (i) −x+1, −y+2, −z.