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

The title compound, C₂₃H₂₆BrN₅O₂, was synthesized by the reaction of 4-[(2,6-dimethyl­phen­yl)amino­carbonyl­methyl]piperazine and 3-(3-nitro­phen­yl)-5-chloro­methyl-1,2,4-oxa­diazole. There are intra­molecular C—H...N and inter­molecular N—H...O and C—H...O hydrogen bonds in the crystal structure.

Key indicators

• Single-crystal X-ray study
• T = 293 K
• Mean [sigma](C-C) = 0.014 Å
• R factor = 0.090
• wR factor = 0.264
• Data-to-parameter ratio = 14.1

checkCIF/PLATON results

No syntax errors found



Alert level B
PLAT027_ALERT_3_B _diffrn_reflns_theta_full (too) Low ............      24.97 Deg.

Alert level C
RFACR01_ALERT_3_C  The value of the weighted R factor is > 0.25
            Weighted R factor given   0.264
RINTA01_ALERT_3_C  The value of Rint is greater than 0.10
            Rint given   0.105
PLAT020_ALERT_3_C The value of Rint is greater than 0.10 .........       0.10
PLAT084_ALERT_2_C High R2 Value ..................................       0.26
PLAT094_ALERT_2_C Ratio of Maximum / Minimum Residual Density ....       2.77
PLAT341_ALERT_3_C Low Bond Precision on C-C bonds (x 1000) Ang ...         14
PLAT380_ALERT_4_C Check Incorrectly? Oriented X(sp2)-Methyl Moiety         C7

Alert level G
PLAT199_ALERT_1_G Check the Reported _cell_measurement_temperature        293 K
PLAT200_ALERT_1_G Check the Reported _diffrn_ambient_temperature .        293 K

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

   2 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
   2 ALERT type 2 Indicator that the structure model may be wrong or deficient
   5 ALERT type 3 Indicator that the structure quality may be low
   1 ALERT type 4 Improvement, methodology, query or suggestion
   0 ALERT type 5 Informative message, check

---

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.

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

Crystal data

C23H26BrN5O2	F(000) = 1000
Mr = 484.40	Dx = 1.422 Mg m^−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 25 reflections
a = 7.2000 (14) Å	θ = 9–12°
b = 9.5300 (19) Å	µ = 1.85 mm^−1
c = 33.089 (7) Å	T = 293 K
β = 94.71 (3)°	Block, colourless
V = 2262.8 (8) Å^3	0.30 × 0.30 × 0.10 mm
Z = 4

Data collection

Enraf–Nonius CAD-4 diffractometer	2155 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	Rint = 0.105
Graphite monochromator	θmax = 25.0°, θmin = 1.2°
ω/2θ scans	h = 0→8
Absorption correction: ψ scan (North et al., 1968)	k = 0→11
Tmin = 0.607, Tmax = 0.837	l = −39→39
4309 measured reflections	3 standard reflections every 200 reflections
3966 independent reflections	intensity decay: 3%

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)] = 0.090	H-atom parameters constrained
wR(F^2) = 0.264	w = 1/[σ^2(Fo^2) + (0.1P)^2 + 21P] where P = (Fo^2 + 2Fc^2)/3
S = 0.97	(Δ/σ)max = 0.001
3966 reflections	Δρmax = 1.24 e Å^−3
281 parameters	Δρmin = −0.45 e Å^−3
0 restraints	Extinction correction: SHELXL97 (Sheldrick, 1997), Fc^*=kFc[1+0.001xFc^2λ^3/sin(2θ)]^-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.015 (2)

Special details

Experimental. Spectroscopic analysis: ¹H NMR (CDCl₃, δ, p.p.m.): 8.56 (s, 1H), 7.94–7.99 (m, 2H), 7.60–7.64 (m, 2H), 7.08–7.09 (m, 3H), 3.95(s, 2H), 3.23 (s, 2H), 2.79 (m, 8H), 2.21 (s, 6H).

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
Br	1.77399 (16)	0.53905 (13)	1.09057 (4)	0.0669 (5)
O1	0.4116 (9)	0.1661 (6)	0.74863 (19)	0.0482 (17)
O2	1.0666 (10)	0.0275 (7)	0.9535 (2)	0.063 (2)
N1	0.3852 (9)	0.3933 (7)	0.7287 (2)	0.0349 (17)
H1A	0.4368	0.4747	0.7299	0.042*
N2	0.6667 (9)	0.2423 (7)	0.8134 (2)	0.0341 (16)
N3	0.7290 (10)	0.1973 (7)	0.8990 (2)	0.0389 (17)
N4	1.0000 (11)	0.2304 (8)	0.9803 (2)	0.0458 (19)
N5	1.2300 (12)	0.0740 (9)	0.9760 (3)	0.058 (2)
C1	−0.1165 (17)	0.3519 (15)	0.6556 (4)	0.078 (4)
H1B	−0.2265	0.3456	0.6389	0.094*
C2	−0.1098 (13)	0.4316 (13)	0.6908 (4)	0.064 (3)
H2A	−0.2165	0.4773	0.6979	0.077*
C3	0.0549 (13)	0.4436 (9)	0.7155 (3)	0.047 (2)
C4	0.2137 (12)	0.3762 (9)	0.7032 (3)	0.041 (2)
C5	0.2095 (13)	0.2957 (10)	0.6690 (3)	0.049 (3)
C6	0.0398 (16)	0.2829 (12)	0.6456 (4)	0.066 (3)
H6A	0.0330	0.2261	0.6227	0.079*
C7	0.3779 (14)	0.2262 (11)	0.6550 (3)	0.056 (3)
H7A	0.4828	0.2437	0.6742	0.084*
H7B	0.4029	0.2632	0.6290	0.084*
H7C	0.3567	0.1270	0.6528	0.084*
C8	0.0656 (14)	0.5280 (11)	0.7543 (3)	0.062 (3)
H8A	0.1904	0.5248	0.7669	0.093*
H8B	−0.0186	0.4892	0.7723	0.093*
H8C	0.0317	0.6236	0.7482	0.093*
C9	0.4682 (12)	0.2891 (9)	0.7506 (3)	0.037 (2)
C10	0.6375 (12)	0.3326 (9)	0.7779 (3)	0.040 (2)
H10A	0.7470	0.3290	0.7627	0.049*
H10B	0.6219	0.4287	0.7867	0.049*
C11	0.5177 (13)	0.2600 (10)	0.8403 (3)	0.048 (2)
H11A	0.3988	0.2380	0.8258	0.058*
H11B	0.5139	0.3570	0.8492	0.058*
C12	0.5481 (13)	0.1656 (10)	0.8768 (3)	0.045 (2)
H12A	0.4487	0.1794	0.8945	0.054*
H12B	0.5457	0.0683	0.8682	0.054*
C13	0.8765 (12)	0.1768 (9)	0.8722 (2)	0.038 (2)
H13A	0.8778	0.0796	0.8635	0.045*
H13B	0.9961	0.1975	0.8866	0.045*
C14	0.8468 (13)	0.2726 (9)	0.8349 (3)	0.043 (2)
H14A	0.8513	0.3700	0.8434	0.051*
H14B	0.9452	0.2572	0.8171	0.051*
C15	0.7549 (14)	0.1052 (10)	0.9338 (3)	0.050 (2)
H15A	0.7483	0.0084	0.9248	0.059*
H15B	0.6553	0.1206	0.9514	0.059*
C16	0.9389 (14)	0.1303 (10)	0.9573 (3)	0.045 (2)
C17	1.1831 (13)	0.1950 (9)	0.9910 (3)	0.044 (2)
C18	1.3174 (14)	0.2760 (9)	1.0174 (3)	0.045 (2)
C19	1.2762 (14)	0.4097 (10)	1.0297 (3)	0.047 (2)
H19A	1.1586	0.4473	1.0230	0.056*
C20	1.4108 (14)	0.4885 (10)	1.0524 (3)	0.051 (3)
H20A	1.3829	0.5784	1.0610	0.062*
C21	1.5840 (13)	0.4329 (10)	1.0618 (3)	0.048 (2)
C22	1.6288 (14)	0.2997 (10)	1.0489 (3)	0.054 (3)
H22A	1.7478	0.2632	1.0548	0.064*
C23	1.4934 (14)	0.2224 (9)	1.0271 (3)	0.049 (2)
H23A	1.5212	0.1322	1.0187	0.058*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
Br	0.0612 (7)	0.0596 (8)	0.0786 (9)	−0.0045 (6)	−0.0014 (5)	−0.0104 (6)
O1	0.059 (4)	0.026 (3)	0.056 (4)	−0.007 (3)	−0.010 (3)	0.002 (3)
O2	0.079 (5)	0.048 (4)	0.060 (4)	0.016 (4)	−0.010 (4)	−0.014 (4)
N1	0.026 (3)	0.026 (4)	0.051 (5)	−0.002 (3)	−0.005 (3)	0.007 (3)
N2	0.035 (4)	0.031 (4)	0.037 (4)	0.003 (3)	0.000 (3)	0.005 (3)
N3	0.051 (4)	0.036 (4)	0.029 (4)	−0.003 (3)	0.003 (3)	0.000 (3)
N4	0.048 (5)	0.041 (4)	0.047 (5)	0.007 (4)	−0.005 (4)	−0.005 (4)
N5	0.069 (6)	0.052 (5)	0.051 (5)	0.011 (4)	−0.007 (4)	−0.010 (4)
C1	0.056 (8)	0.100 (10)	0.073 (9)	−0.025 (7)	−0.024 (6)	0.020 (8)
C2	0.024 (5)	0.096 (9)	0.074 (8)	−0.002 (5)	0.010 (5)	0.029 (7)
C3	0.047 (5)	0.038 (5)	0.057 (6)	−0.005 (4)	0.012 (5)	0.015 (5)
C4	0.043 (5)	0.027 (4)	0.051 (6)	0.000 (4)	0.002 (4)	0.006 (4)
C5	0.041 (5)	0.037 (5)	0.069 (7)	−0.016 (4)	0.005 (5)	0.012 (5)
C6	0.058 (7)	0.059 (7)	0.077 (8)	−0.022 (6)	−0.013 (6)	0.006 (6)
C7	0.075 (7)	0.056 (6)	0.038 (5)	0.000 (6)	0.012 (5)	−0.004 (5)
C8	0.049 (6)	0.051 (6)	0.089 (8)	0.001 (5)	0.022 (6)	0.000 (6)
C9	0.047 (6)	0.031 (5)	0.033 (5)	0.004 (4)	0.007 (4)	−0.003 (4)
C10	0.043 (5)	0.033 (5)	0.044 (5)	−0.005 (4)	−0.001 (4)	0.009 (4)
C11	0.049 (6)	0.044 (6)	0.051 (6)	−0.002 (5)	0.000 (5)	0.002 (5)
C12	0.051 (6)	0.048 (6)	0.037 (5)	−0.006 (5)	0.002 (4)	0.004 (4)
C13	0.037 (5)	0.039 (5)	0.037 (5)	0.008 (4)	0.006 (4)	−0.003 (4)
C14	0.047 (5)	0.034 (5)	0.046 (5)	−0.006 (4)	−0.002 (4)	0.002 (4)
C15	0.067 (7)	0.043 (5)	0.038 (5)	−0.005 (5)	0.002 (5)	0.007 (4)
C16	0.057 (6)	0.044 (6)	0.037 (5)	0.006 (5)	0.021 (5)	0.009 (4)
C17	0.060 (6)	0.034 (5)	0.037 (5)	0.010 (4)	−0.001 (4)	0.003 (4)
C18	0.062 (6)	0.034 (5)	0.039 (5)	0.015 (5)	0.007 (5)	0.001 (4)
C19	0.050 (6)	0.047 (6)	0.044 (5)	0.011 (5)	0.005 (5)	−0.001 (4)
C20	0.062 (6)	0.046 (6)	0.047 (6)	0.016 (5)	0.011 (5)	−0.009 (5)
C21	0.056 (6)	0.046 (6)	0.046 (6)	0.002 (5)	0.024 (5)	0.001 (4)
C22	0.053 (6)	0.044 (6)	0.065 (7)	0.008 (5)	0.005 (5)	−0.001 (5)
C23	0.063 (6)	0.029 (5)	0.054 (6)	0.017 (5)	0.008 (5)	−0.006 (4)

Geometric parameters (Å, º)

Br—C21	1.894 (10)	C8—H8A	0.9600
O1—C9	1.240 (10)	C8—H8B	0.9600
O2—C16	1.356 (11)	C8—H8C	0.9600
O2—N5	1.411 (11)	C9—C10	1.514 (12)
N1—C9	1.341 (10)	C10—H10A	0.9700
N1—C4	1.447 (11)	C10—H10B	0.9700
N1—H1A	0.8600	C11—C12	1.507 (12)
N2—C14	1.456 (11)	C11—H11A	0.9700
N2—C10	1.457 (10)	C11—H11B	0.9700
N2—C11	1.460 (11)	C12—H12A	0.9700
N3—C15	1.448 (11)	C12—H12B	0.9700
N3—C13	1.453 (11)	C13—C14	1.534 (12)
N3—C12	1.473 (11)	C13—H13A	0.9700
N4—C16	1.275 (12)	C13—H13B	0.9700
N4—C17	1.379 (11)	C14—H14A	0.9700
N5—C17	1.310 (12)	C14—H14B	0.9700
C1—C6	1.367 (17)	C15—C16	1.499 (13)
C1—C2	1.387 (17)	C15—H15A	0.9700
C1—H1B	0.9300	C15—H15B	0.9700
C2—C3	1.389 (14)	C17—C18	1.468 (13)
C2—H2A	0.9300	C18—C19	1.377 (13)
C3—C4	1.400 (13)	C18—C23	1.380 (13)
C3—C8	1.510 (14)	C19—C20	1.395 (14)
C4—C5	1.364 (13)	C19—H19A	0.9300
C5—C6	1.397 (13)	C20—C21	1.367 (13)
C5—C7	1.489 (14)	C20—H20A	0.9300
C6—H6A	0.9300	C21—C22	1.387 (13)
C7—H7A	0.9600	C22—C23	1.377 (13)
C7—H7B	0.9600	C22—H22A	0.9300
C7—H7C	0.9600	C23—H23A	0.9300
C16—O2—N5	105.5 (7)	C12—C11—H11A	109.5
C9—N1—C4	123.6 (7)	N2—C11—H11B	109.5
C9—N1—H1A	118.2	C12—C11—H11B	109.5
C4—N1—H1A	118.2	H11A—C11—H11B	108.1
C14—N2—C10	109.9 (6)	N3—C12—C11	110.0 (7)
C14—N2—C11	110.4 (7)	N3—C12—H12A	109.7
C10—N2—C11	111.1 (7)	C11—C12—H12A	109.7
C15—N3—C13	110.6 (7)	N3—C12—H12B	109.7
C15—N3—C12	108.9 (7)	C11—C12—H12B	109.7
C13—N3—C12	109.1 (7)	H12A—C12—H12B	108.2
C16—N4—C17	104.3 (8)	N3—C13—C14	110.5 (7)
C17—N5—O2	104.3 (8)	N3—C13—H13A	109.5
C6—C1—C2	119.6 (10)	C14—C13—H13A	109.5
C6—C1—H1B	120.2	N3—C13—H13B	109.5
C2—C1—H1B	120.2	C14—C13—H13B	109.5
C1—C2—C3	120.6 (10)	H13A—C13—H13B	108.1
C1—C2—H2A	119.7	N2—C14—C13	109.6 (7)
C3—C2—H2A	119.7	N2—C14—H14A	109.8
C2—C3—C4	118.0 (10)	C13—C14—H14A	109.8
C2—C3—C8	121.7 (9)	N2—C14—H14B	109.8
C4—C3—C8	120.3 (9)	C13—C14—H14B	109.8
C5—C4—C3	122.4 (9)	H14A—C14—H14B	108.2
C5—C4—N1	120.4 (8)	N3—C15—C16	111.5 (8)
C3—C4—N1	117.2 (8)	N3—C15—H15A	109.3
C4—C5—C6	117.9 (10)	C16—C15—H15A	109.3
C4—C5—C7	123.0 (9)	N3—C15—H15B	109.3
C6—C5—C7	119.0 (10)	C16—C15—H15B	109.3
C1—C6—C5	121.5 (12)	H15A—C15—H15B	108.0
C1—C6—H6A	119.2	N4—C16—O2	113.1 (9)
C5—C6—H6A	119.2	N4—C16—C15	132.5 (9)
C5—C7—H7A	109.5	O2—C16—C15	114.5 (9)
C5—C7—H7B	109.5	N5—C17—N4	112.8 (9)
H7A—C7—H7B	109.5	N5—C17—C18	120.7 (9)
C5—C7—H7C	109.5	N4—C17—C18	126.4 (8)
H7A—C7—H7C	109.5	C19—C18—C23	119.3 (9)
H7B—C7—H7C	109.5	C19—C18—C17	121.1 (9)
C3—C8—H8A	109.5	C23—C18—C17	119.4 (8)
C3—C8—H8B	109.5	C18—C19—C20	120.0 (9)
H8A—C8—H8B	109.5	C18—C19—H19A	120.0
C3—C8—H8C	109.5	C20—C19—H19A	120.0
H8A—C8—H8C	109.5	C21—C20—C19	119.6 (9)
H8B—C8—H8C	109.5	C21—C20—H20A	120.2
O1—C9—N1	122.8 (8)	C19—C20—H20A	120.2
O1—C9—C10	122.3 (8)	C20—C21—C22	121.0 (10)
N1—C9—C10	114.9 (7)	C20—C21—Br	121.0 (7)
N2—C10—C9	112.0 (7)	C22—C21—Br	117.9 (8)
N2—C10—H10A	109.2	C23—C22—C21	118.6 (9)
C9—C10—H10A	109.2	C23—C22—H22A	120.7
N2—C10—H10B	109.2	C21—C22—H22A	120.7
C9—C10—H10B	109.2	C22—C23—C18	121.4 (9)
H10A—C10—H10B	107.9	C22—C23—H23A	119.3
N2—C11—C12	110.7 (8)	C18—C23—H23A	119.3
N2—C11—H11A	109.5
C16—O2—N5—C17	1.0 (10)	C10—N2—C14—C13	−179.8 (7)
C6—C1—C2—C3	1.1 (17)	C11—N2—C14—C13	57.3 (9)
C1—C2—C3—C4	1.6 (15)	N3—C13—C14—N2	−58.7 (9)
C1—C2—C3—C8	−179.2 (10)	C13—N3—C15—C16	58.9 (10)
C2—C3—C4—C5	−2.7 (13)	C12—N3—C15—C16	178.8 (8)
C8—C3—C4—C5	178.1 (9)	C17—N4—C16—O2	2.8 (10)
C2—C3—C4—N1	178.3 (8)	C17—N4—C16—C15	−177.0 (9)
C8—C3—C4—N1	−1.0 (12)	N5—O2—C16—N4	−2.5 (10)
C9—N1—C4—C5	−67.9 (11)	N5—O2—C16—C15	177.3 (7)
C9—N1—C4—C3	111.2 (9)	N3—C15—C16—N4	72.1 (13)
C3—C4—C5—C6	0.9 (14)	N3—C15—C16—O2	−107.7 (9)
N1—C4—C5—C6	179.9 (8)	O2—N5—C17—N4	0.7 (10)
C3—C4—C5—C7	178.4 (9)	O2—N5—C17—C18	178.7 (8)
N1—C4—C5—C7	−2.5 (13)	C16—N4—C17—N5	−2.1 (11)
C2—C1—C6—C5	−3.0 (18)	C16—N4—C17—C18	180.0 (9)
C4—C5—C6—C1	2.0 (15)	N5—C17—C18—C19	173.0 (9)
C7—C5—C6—C1	−175.6 (10)	N4—C17—C18—C19	−9.2 (15)
C4—N1—C9—O1	5.3 (13)	N5—C17—C18—C23	−1.3 (14)
C4—N1—C9—C10	−175.1 (7)	N4—C17—C18—C23	176.4 (9)
C14—N2—C10—C9	170.3 (7)	C23—C18—C19—C20	−1.0 (14)
C11—N2—C10—C9	−67.2 (9)	C17—C18—C19—C20	−175.4 (9)
O1—C9—C10—N2	−28.2 (12)	C18—C19—C20—C21	0.7 (15)
N1—C9—C10—N2	152.2 (7)	C19—C20—C21—C22	0.6 (15)
C14—N2—C11—C12	−58.2 (9)	C19—C20—C21—Br	177.4 (7)
C10—N2—C11—C12	179.6 (7)	C20—C21—C22—C23	−1.6 (15)
C15—N3—C12—C11	−179.9 (8)	Br—C21—C22—C23	−178.5 (7)
C13—N3—C12—C11	−59.1 (9)	C21—C22—C23—C18	1.3 (15)
N2—C11—C12—N3	58.7 (10)	C19—C18—C23—C22	0.0 (15)
C15—N3—C13—C14	179.0 (7)	C17—C18—C23—C22	174.5 (9)
C12—N3—C13—C14	59.2 (9)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1A···O1^i	0.86	2.21	3.047 (9)	163
C7—H7A···N1	0.96	2.45	2.909 (12)	109
C8—H8A···N1	0.96	2.33	2.825 (12)	111
C10—H10B···O1^i	0.97	2.55	3.309 (10)	135
C23—H23A···N5	0.93	2.49	2.816 (13)	101

Symmetry code: (i) −x+1, y+1/2, −z+3/2.