4-{[3-(2-Chloro­phen­yl)-1,2,4-oxadiazol-5-yl]meth­yl}-1-[(2,6-dimethyl­phen­yl)amino­carbon­yl­meth­yl]piperazine

The title compound, C₂₃H₂₆ClN₅O₂, was synthesized by the reaction of 4-[(2,6-dimethyl­phen­yl)amino­carbonyl­meth­yl]­piperazine and 5-chloro­meth­yl-3-(2-chloro­phen­yl)-1,2,4-oxadiazole. In the structure, there are intra­molecular C—H...N, N—H...N and C—H...O hydrogen bonds, and inter­molecular N—H...O hydrogen bonds.

Key indicators

• Single-crystal X-ray study
• T = 293 K
• Mean [sigma](C-C) = 0.005 Å
• R factor = 0.058
• wR factor = 0.201
• Data-to-parameter ratio = 13.7

checkCIF/PLATON results

No syntax errors found



Alert level C
PLAT128_ALERT_4_C Non-standard setting of Space group P21/c   ....    P21/a
PLAT199_ALERT_1_C Check the Reported _cell_measurement_temperature        293 K
PLAT200_ALERT_1_C Check the Reported _diffrn_ambient_temperature .        293 K
PLAT340_ALERT_3_C Low Bond Precision on C-C bonds (x 1000) Ang ...          5
PLAT380_ALERT_4_C Check Incorrectly? Oriented X(sp2)-Methyl Moiety        C23

   0 ALERT level A = In general: serious problem
   0 ALERT level B = Potentially serious problem
   5 ALERT level C = Check and explain
   0 ALERT level G = General alerts; check

   2 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
   0 ALERT type 2 Indicator that the structure model may be wrong or deficient
   1 ALERT type 3 Indicator that the structure quality may be low
   2 ALERT type 4 Improvement, methodology, query or suggestion

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Computing details

Data collection: CAD-4 Software (Enraf–Nonius, 1989); cell refinement: CAD-4 Software; data reduction: XCAD4 (Harms & Wocadlo, 1995); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: SHELXTL (Siemens,1996); software used to prepare material for publication: SHELXL97.

4-{[3-(2-Chlorophenyl)-1,2,4-oxadiazol-5-yl]methyl}-1-[(2,6- dimethylphenyl)aminocarbonylmethyl]piperazine

Crystal data

C23H26ClN5O2	F(000) = 928
Mr = 439.94	Dx = 1.327 Mg m^−3
Monoclinic, P21/a	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2yab	Cell parameters from 25 reflections
a = 12.296 (1) Å	θ = 10–13°
b = 10.587 (2) Å	µ = 0.20 mm^−1
c = 17.164 (2) Å	T = 293 K
β = 99.77 (3)°	Block, colourless
V = 2201.8 (6) Å^3	0.4 × 0.3 × 0.2 mm
Z = 4

Data collection

Enraf–Nonius CAD-4 diffractometer	Rint = 0.030
Radiation source: fine-focus sealed tube	θmax = 25.0°, θmin = 2.3°
Graphite monochromator	h = −14→0
ω/2θ scans	k = 0→12
4061 measured reflections	l = −20→20
3861 independent reflections	3 standard reflections every 200 reflections
2427 reflections with I > 2σ(I)	intensity decay: none

Refinement

Refinement on F^2	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F^2 > 2σ(F^2)] = 0.058	H-atom parameters constrained
wR(F^2) = 0.201	w = 1/[σ^2(Fo^2) + (0.1259P)^2] where P = (Fo^2 + 2Fc^2)/3
S = 1.01	(Δ/σ)max < 0.001
3861 reflections	Δρmax = 0.41 e Å^−3
281 parameters	Δρmin = −0.30 e Å^−3
0 restraints	Extinction correction: SHELXL97, Fc^*=kFc[1+0.001xFc^2λ^3/sin(2θ)]^-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.023 (4)

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
Cl	0.70877 (8)	0.22764 (10)	1.15809 (5)	0.0608 (4)
O1	0.4167 (2)	0.2981 (3)	0.99003 (15)	0.0661 (8)
O2	0.2535 (2)	−0.1210 (2)	0.48511 (14)	0.0527 (7)
N1	0.5131 (3)	0.3232 (4)	1.04493 (17)	0.0654 (10)
N2	0.5439 (2)	0.3472 (3)	0.92129 (16)	0.0535 (8)
N3	0.3696 (2)	0.1896 (3)	0.80020 (15)	0.0445 (7)
N4	0.3633 (2)	0.0813 (3)	0.64604 (15)	0.0406 (7)
N5	0.2348 (2)	0.0903 (2)	0.49867 (14)	0.0397 (7)
H5A	0.2621	0.1559	0.5244	0.048*
C1	0.9115 (3)	0.4799 (4)	1.0904 (2)	0.0627 (11)
H1B	0.9810	0.5122	1.1103	0.075*
C2	0.8651 (3)	0.3897 (4)	1.1322 (2)	0.0546 (10)
H2B	0.9042	0.3587	1.1795	0.065*
C3	0.7597 (3)	0.3448 (3)	1.10373 (18)	0.0447 (8)
C4	0.6990 (3)	0.3899 (3)	1.03310 (18)	0.0429 (8)
C5	0.7497 (3)	0.4767 (3)	0.9908 (2)	0.0528 (9)
H5B	0.7125	0.5052	0.9422	0.063*
C6	0.8546 (3)	0.5222 (4)	1.0191 (2)	0.0613 (10)
H6A	0.8867	0.5813	0.9899	0.074*
C7	0.5849 (3)	0.3516 (3)	1.00099 (18)	0.0419 (8)
C8	0.4427 (3)	0.3149 (3)	0.9191 (2)	0.0479 (9)
C9	0.3508 (3)	0.2962 (4)	0.8509 (2)	0.0602 (10)
H9A	0.2826	0.2821	0.8709	0.072*
H9B	0.3419	0.3727	0.8193	0.072*
C10	0.2646 (3)	0.1553 (4)	0.7496 (2)	0.0527 (9)
H10A	0.2355	0.2278	0.7182	0.063*
H10B	0.2112	0.1306	0.7823	0.063*
C11	0.2826 (3)	0.0478 (4)	0.6957 (2)	0.0528 (9)
H11A	0.3083	−0.0258	0.7272	0.063*
H11B	0.2132	0.0262	0.6625	0.063*
C12	0.4677 (3)	0.1107 (4)	0.69733 (19)	0.0508 (9)
H12A	0.5229	0.1323	0.6654	0.061*
H12B	0.4935	0.0374	0.7290	0.061*
C13	0.4519 (3)	0.2200 (4)	0.7507 (2)	0.0518 (9)
H13A	0.5216	0.2399	0.7841	0.062*
H13B	0.4281	0.2938	0.7188	0.062*
C14	0.3749 (3)	−0.0180 (3)	0.59039 (19)	0.0523 (9)
H14A	0.3786	−0.0986	0.6176	0.063*
H14B	0.4440	−0.0063	0.5712	0.063*
C15	0.2808 (3)	−0.0222 (3)	0.51981 (18)	0.0401 (8)
C16	0.1426 (2)	0.1083 (3)	0.43565 (19)	0.0367 (7)
C17	0.0442 (3)	0.1530 (3)	0.4556 (2)	0.0430 (8)
C18	−0.0437 (3)	0.1719 (3)	0.3946 (3)	0.0570 (10)
H18A	−0.1101	0.2026	0.4061	0.068*
C19	−0.0344 (3)	0.1463 (4)	0.3179 (3)	0.0645 (12)
H19A	−0.0950	0.1577	0.2780	0.077*
C20	0.0645 (3)	0.1035 (4)	0.2991 (2)	0.0589 (10)
H20A	0.0702	0.0882	0.2466	0.071*
C21	0.1555 (3)	0.0833 (3)	0.35841 (19)	0.0446 (8)
C22	0.0331 (3)	0.1813 (4)	0.5389 (2)	0.0588 (10)
H22A	−0.0401	0.2117	0.5405	0.088*
H22B	0.0859	0.2446	0.5598	0.088*
H22C	0.0462	0.1058	0.5701	0.088*
C23	0.2630 (3)	0.0395 (4)	0.3375 (2)	0.0572 (10)
H23A	0.3165	0.0303	0.3849	0.086*
H23B	0.2889	0.1005	0.3035	0.086*
H23C	0.2525	−0.0403	0.3108	0.086*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
Cl	0.0680 (7)	0.0673 (7)	0.0437 (5)	−0.0099 (5)	0.0002 (4)	0.0126 (4)
O1	0.0465 (15)	0.099 (2)	0.0523 (16)	−0.0037 (14)	0.0055 (12)	0.0066 (15)
O2	0.0598 (16)	0.0336 (13)	0.0608 (15)	0.0034 (11)	−0.0008 (12)	−0.0033 (11)
N1	0.0505 (19)	0.101 (3)	0.0426 (17)	−0.0049 (18)	0.0022 (15)	0.0029 (17)
N2	0.0495 (18)	0.068 (2)	0.0401 (16)	−0.0052 (15)	−0.0003 (13)	−0.0041 (14)
N3	0.0323 (14)	0.0564 (17)	0.0431 (15)	−0.0039 (12)	0.0014 (12)	−0.0039 (13)
N4	0.0342 (14)	0.0477 (16)	0.0378 (14)	0.0011 (12)	−0.0001 (11)	0.0038 (12)
N5	0.0401 (15)	0.0295 (14)	0.0461 (16)	0.0001 (11)	−0.0020 (12)	−0.0073 (11)
C1	0.057 (2)	0.072 (3)	0.060 (2)	−0.016 (2)	0.0103 (19)	−0.014 (2)
C2	0.053 (2)	0.065 (3)	0.0424 (19)	−0.0063 (19)	−0.0021 (17)	−0.0083 (18)
C3	0.055 (2)	0.0423 (19)	0.0360 (17)	−0.0026 (16)	0.0071 (15)	−0.0040 (14)
C4	0.051 (2)	0.0415 (19)	0.0351 (17)	−0.0027 (15)	0.0045 (14)	−0.0081 (14)
C5	0.063 (2)	0.047 (2)	0.047 (2)	−0.0010 (18)	0.0060 (17)	0.0061 (17)
C6	0.067 (3)	0.054 (2)	0.064 (2)	−0.015 (2)	0.016 (2)	0.0044 (19)
C7	0.050 (2)	0.0360 (18)	0.0385 (17)	0.0011 (15)	0.0054 (15)	−0.0015 (14)
C8	0.048 (2)	0.045 (2)	0.048 (2)	0.0081 (16)	0.0017 (16)	−0.0066 (16)
C9	0.051 (2)	0.072 (3)	0.055 (2)	0.0093 (19)	−0.0008 (18)	−0.0113 (19)
C10	0.0328 (18)	0.074 (3)	0.049 (2)	−0.0025 (17)	0.0009 (15)	0.0021 (18)
C11	0.047 (2)	0.058 (2)	0.051 (2)	−0.0112 (17)	0.0033 (16)	0.0072 (18)
C12	0.0330 (18)	0.072 (3)	0.0454 (19)	0.0006 (16)	−0.0001 (14)	0.0045 (17)
C13	0.0433 (19)	0.064 (2)	0.0455 (19)	−0.0141 (17)	0.0012 (15)	−0.0005 (17)
C14	0.054 (2)	0.051 (2)	0.0484 (19)	0.0137 (17)	0.0005 (16)	−0.0001 (17)
C15	0.0426 (18)	0.0340 (18)	0.0437 (18)	0.0032 (14)	0.0078 (14)	0.0034 (14)
C16	0.0317 (16)	0.0266 (16)	0.0488 (18)	−0.0036 (12)	−0.0017 (14)	−0.0014 (13)
C17	0.0373 (18)	0.0282 (17)	0.062 (2)	−0.0028 (14)	0.0033 (15)	0.0039 (15)
C18	0.041 (2)	0.044 (2)	0.084 (3)	−0.0004 (16)	0.0042 (19)	0.014 (2)
C19	0.044 (2)	0.065 (3)	0.075 (3)	−0.0110 (19)	−0.0151 (19)	0.026 (2)
C20	0.064 (3)	0.061 (2)	0.047 (2)	−0.016 (2)	−0.0042 (18)	0.0029 (18)
C21	0.047 (2)	0.0395 (18)	0.0441 (19)	−0.0067 (15)	−0.0006 (15)	−0.0015 (15)
C22	0.051 (2)	0.052 (2)	0.079 (3)	−0.0033 (18)	0.0239 (19)	−0.0107 (19)
C23	0.058 (2)	0.064 (2)	0.050 (2)	−0.0029 (19)	0.0104 (18)	−0.0089 (18)

Geometric parameters (Å, º)

Cl—C3	1.732 (3)	C10—C11	1.506 (5)
O1—C8	1.321 (4)	C10—H10A	0.9700
O1—N1	1.408 (4)	C10—H10B	0.9700
O2—C15	1.221 (4)	C11—H11A	0.9700
N1—C7	1.290 (4)	C11—H11B	0.9700
N2—C8	1.285 (4)	C12—C13	1.508 (5)
N2—C7	1.376 (4)	C12—H12A	0.9700
N3—C13	1.464 (4)	C12—H12B	0.9700
N3—C9	1.467 (4)	C13—H13A	0.9700
N3—C10	1.474 (4)	C13—H13B	0.9700
N4—C14	1.444 (4)	C14—C15	1.528 (4)
N4—C11	1.458 (4)	C14—H14A	0.9700
N4—C12	1.462 (4)	C14—H14B	0.9700
N5—C15	1.342 (4)	C16—C21	1.387 (5)
N5—C16	1.440 (4)	C16—C17	1.395 (4)
N5—H5A	0.8600	C17—C18	1.384 (5)
C1—C2	1.375 (5)	C17—C22	1.490 (5)
C1—C6	1.378 (5)	C18—C19	1.368 (6)
C1—H1B	0.9300	C18—H18A	0.9300
C2—C3	1.389 (5)	C19—C20	1.386 (6)
C2—H2B	0.9300	C19—H19A	0.9300
C3—C4	1.395 (4)	C20—C21	1.395 (5)
C4—C5	1.384 (5)	C20—H20A	0.9300
C4—C7	1.475 (4)	C21—C23	1.501 (5)
C5—C6	1.385 (5)	C22—H22A	0.9600
C5—H5B	0.9300	C22—H22B	0.9600
C6—H6A	0.9300	C22—H22C	0.9600
C8—C9	1.496 (5)	C23—H23A	0.9600
C9—H9A	0.9700	C23—H23B	0.9600
C9—H9B	0.9700	C23—H23C	0.9600
C8—O1—N1	106.5 (3)	H11A—C11—H11B	108.0
C7—N1—O1	103.5 (3)	N4—C12—C13	109.8 (3)
C8—N2—C7	103.1 (3)	N4—C12—H12A	109.7
C13—N3—C9	111.7 (3)	C13—C12—H12A	109.7
C13—N3—C10	109.5 (3)	N4—C12—H12B	109.7
C9—N3—C10	109.2 (3)	C13—C12—H12B	109.7
C14—N4—C11	111.3 (3)	H12A—C12—H12B	108.2
C14—N4—C12	112.2 (3)	N3—C13—C12	110.9 (3)
C11—N4—C12	108.4 (2)	N3—C13—H13A	109.5
C15—N5—C16	124.2 (3)	C12—C13—H13A	109.5
C15—N5—H5A	117.9	N3—C13—H13B	109.5
C16—N5—H5A	117.9	C12—C13—H13B	109.5
C2—C1—C6	119.7 (4)	H13A—C13—H13B	108.1
C2—C1—H1B	120.1	N4—C14—C15	113.5 (3)
C6—C1—H1B	120.1	N4—C14—H14A	108.9
C1—C2—C3	119.9 (3)	C15—C14—H14A	108.9
C1—C2—H2B	120.0	N4—C14—H14B	108.9
C3—C2—H2B	120.0	C15—C14—H14B	108.9
C2—C3—C4	121.2 (3)	H14A—C14—H14B	107.7
C2—C3—Cl	117.1 (3)	O2—C15—N5	124.0 (3)
C4—C3—Cl	121.6 (3)	O2—C15—C14	121.3 (3)
C5—C4—C3	117.5 (3)	N5—C15—C14	114.6 (3)
C5—C4—C7	118.1 (3)	C21—C16—C17	122.9 (3)
C3—C4—C7	124.4 (3)	C21—C16—N5	119.3 (3)
C4—C5—C6	121.5 (3)	C17—C16—N5	117.8 (3)
C4—C5—H5B	119.3	C18—C17—C16	117.5 (3)
C6—C5—H5B	119.3	C18—C17—C22	120.6 (3)
C1—C6—C5	120.1 (4)	C16—C17—C22	121.9 (3)
C1—C6—H6A	120.0	C19—C18—C17	121.1 (4)
C5—C6—H6A	120.0	C19—C18—H18A	119.4
N1—C7—N2	113.7 (3)	C17—C18—H18A	119.4
N1—C7—C4	123.2 (3)	C18—C19—C20	120.5 (3)
N2—C7—C4	123.1 (3)	C18—C19—H19A	119.7
N2—C8—O1	113.2 (3)	C20—C19—H19A	119.7
N2—C8—C9	131.0 (3)	C19—C20—C21	120.5 (4)
O1—C8—C9	115.8 (3)	C19—C20—H20A	119.7
N3—C9—C8	113.1 (3)	C21—C20—H20A	119.7
N3—C9—H9A	109.0	C16—C21—C20	117.4 (3)
C8—C9—H9A	109.0	C16—C21—C23	122.4 (3)
N3—C9—H9B	109.0	C20—C21—C23	120.2 (3)
C8—C9—H9B	109.0	C17—C22—H22A	109.5
H9A—C9—H9B	107.8	C17—C22—H22B	109.5
N3—C10—C11	110.1 (3)	H22A—C22—H22B	109.5
N3—C10—H10A	109.6	C17—C22—H22C	109.5
C11—C10—H10A	109.6	H22A—C22—H22C	109.5
N3—C10—H10B	109.6	H22B—C22—H22C	109.5
C11—C10—H10B	109.6	C21—C23—H23A	109.5
H10A—C10—H10B	108.2	C21—C23—H23B	109.5
N4—C11—C10	111.1 (3)	H23A—C23—H23B	109.5
N4—C11—H11A	109.4	C21—C23—H23C	109.5
C10—C11—H11A	109.4	H23A—C23—H23C	109.5
N4—C11—H11B	109.4	H23B—C23—H23C	109.5
C10—C11—H11B	109.4
C8—O1—N1—C7	−0.1 (4)	C14—N4—C11—C10	−175.8 (3)
C6—C1—C2—C3	−2.2 (6)	C12—N4—C11—C10	60.3 (4)
C1—C2—C3—C4	−0.2 (5)	N3—C10—C11—N4	−58.8 (4)
C1—C2—C3—Cl	177.9 (3)	C14—N4—C12—C13	176.6 (3)
C2—C3—C4—C5	2.8 (5)	C11—N4—C12—C13	−60.1 (4)
Cl—C3—C4—C5	−175.2 (3)	C9—N3—C13—C12	−178.3 (3)
C2—C3—C4—C7	−176.9 (3)	C10—N3—C13—C12	−57.3 (4)
Cl—C3—C4—C7	5.0 (5)	N4—C12—C13—N3	59.9 (4)
C3—C4—C5—C6	−3.1 (5)	C11—N4—C14—C15	77.3 (3)
C7—C4—C5—C6	176.7 (3)	C12—N4—C14—C15	−161.0 (3)
C2—C1—C6—C5	1.9 (6)	C16—N5—C15—O2	4.2 (5)
C4—C5—C6—C1	0.8 (6)	C16—N5—C15—C14	−177.8 (3)
O1—N1—C7—N2	0.0 (4)	N4—C14—C15—O2	−151.5 (3)
O1—N1—C7—C4	177.7 (3)	N4—C14—C15—N5	30.5 (4)
C8—N2—C7—N1	0.2 (4)	C15—N5—C16—C21	−65.7 (4)
C8—N2—C7—C4	−177.5 (3)	C15—N5—C16—C17	115.6 (3)
C5—C4—C7—N1	−146.8 (4)	C21—C16—C17—C18	0.4 (5)
C3—C4—C7—N1	33.0 (5)	N5—C16—C17—C18	179.0 (3)
C5—C4—C7—N2	30.7 (5)	C21—C16—C17—C22	−178.8 (3)
C3—C4—C7—N2	−149.5 (3)	N5—C16—C17—C22	−0.2 (4)
C7—N2—C8—O1	−0.3 (4)	C16—C17—C18—C19	0.7 (5)
C7—N2—C8—C9	178.3 (4)	C22—C17—C18—C19	180.0 (3)
N1—O1—C8—N2	0.3 (4)	C17—C18—C19—C20	−1.6 (6)
N1—O1—C8—C9	−178.5 (3)	C18—C19—C20—C21	1.4 (6)
C13—N3—C9—C8	−74.9 (4)	C17—C16—C21—C20	−0.6 (5)
C10—N3—C9—C8	163.9 (3)	N5—C16—C21—C20	−179.2 (3)
N2—C8—C9—N3	65.8 (5)	C17—C16—C21—C23	177.8 (3)
O1—C8—C9—N3	−115.7 (4)	N5—C16—C21—C23	−0.7 (5)
C13—N3—C10—C11	56.2 (4)	C19—C20—C21—C16	−0.3 (5)
C9—N3—C10—C11	178.8 (3)	C19—C20—C21—C23	−178.8 (3)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
N5—H5A···N4	0.86	2.38	2.747 (4)	106
N5—H5A···O2^i	0.86	2.37	3.070 (3)	138
C13—H13A···N2	0.97	2.59	3.247 (5)	125
C23—H23A···O2	0.96	2.56	3.068 (4)	113
C23—H23A···N5	0.96	2.43	2.896 (4)	110

Symmetry code: (i) −x+1/2, y+1/2, −z+1.