5-(2-Bromo-5-methoxy­phen­yl)-1,3,4-oxadiazol-2-amine

The title compound, C₉H₈BrN₃O₂, crystallizes with two almost identical mol­ecules in the asymmetric unit. The crystal packing is stabilized by N—H...N hydrogen bonds and π–π stacking inter­actions.

Key indicators

• Single-crystal X-ray study
• T = 173 K
• Mean [sigma](C-C) = 0.010 Å
• R factor = 0.073
• wR factor = 0.220
• Data-to-parameter ratio = 13.3

checkCIF/PLATON results

No syntax errors found



Alert level C
PLAT220_ALERT_2_C Large Non-Solvent    C     Ueq(max)/Ueq(min) ...       3.37 Ratio
PLAT222_ALERT_3_C Large Non-Solvent    H     Ueq(max)/Ueq(min) ...       3.48 Ratio
PLAT341_ALERT_3_C Low Bond Precision on C-C bonds (x 1000) Ang ...         10
PLAT431_ALERT_2_C Short Inter HL..A Contact  Br1A   ..  Br1A    ..       3.54 Ang.
PLAT432_ALERT_2_C Short Inter X...Y Contact  C2A    ..  C14A    ..       3.17 Ang.
PLAT720_ALERT_4_C Number of Unusual/Non-Standard Label(s) ........          2

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

   0 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
   3 ALERT type 2 Indicator that the structure model may be wrong or deficient
   2 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

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Computing details

Data collection: X-AREA (Stoe & Cie, 2001); cell refinement: X-AREA; data reduction: X-AREA; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: XP in SHELXTL-Plus (Sheldrick, 1991); software used to prepare material for publication: SHELXL97.

5-(2-Bromo-5-methoxyphenyl)-1,3,4-oxadiazol-2-amine

Crystal data

C9H8BrN3O2	F(000) = 1072
Mr = 270.09	Dx = 1.729 Mg m^−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 9913 reflections
a = 18.1501 (19) Å	θ = 3.6–25.2°
b = 10.3513 (7) Å	µ = 3.94 mm^−1
c = 11.0955 (10) Å	T = 173 K
β = 95.298 (8)°	Plate, colourless
V = 2075.7 (3) Å^3	0.47 × 0.36 × 0.21 mm
Z = 8

Data collection

Stoe IPDS II two-circle diffractometer	3644 independent reflections
Radiation source: fine-focus sealed tube	2876 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.079
ω scans	θmax = 25.0°, θmin = 3.6°
Absorption correction: multi-scan (MULABS; Spek, 2003; Blessing, 1995)	h = −18→21
Tmin = 0.215, Tmax = 0.441	k = −12→12
10488 measured reflections	l = −13→13

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)] = 0.073	H-atom parameters constrained
wR(F^2) = 0.220	w = 1/[σ^2(Fo^2) + (0.1458P)^2 + 1.2938P] where P = (Fo^2 + 2Fc^2)/3
S = 1.05	(Δ/σ)max < 0.001
3644 reflections	Δρmax = 1.77 e Å^−3
274 parameters	Δρmin = −1.42 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: 0.021 (2)

Special details

Experimental. Analysis for C₉H₈BrN₃O₂, found (calculated): C 40 (40.04), H 2.89 (2.99), N 15.36 (15.56)%. Spectroscopic analysis: ¹H NMR (300 MHz, CDCl₃, δ, p.p.m.): 3.84 (s, 3H, –OCH₃), 5.16 (s, 2H, –NH₂), 6.88 (dd, J = 6.7 Hz, 1H, ArH), 7.36 (d, J = 2.28 Hz, 1H, ArH), 7.59 (d, J = 6.7 Hz, 1H, ArH); FAB-MS: m/z 270 (100%, M⁺), m/z 271 (50%, M+1), m/z 272 (98%, M+2).

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
Br1	0.51499 (5)	0.47549 (8)	0.17728 (7)	0.0398 (4)
C1	0.5573 (4)	0.6682 (6)	0.4087 (5)	0.0205 (14)
O1	0.5742 (3)	0.7368 (4)	0.5157 (4)	0.0204 (10)
C2	0.6471 (5)	0.7659 (7)	0.5122 (6)	0.0267 (16)
N1	0.6142 (4)	0.6600 (6)	0.3468 (5)	0.0255 (13)
N2	0.6739 (3)	0.7235 (6)	0.4141 (5)	0.0254 (13)
N3	0.6819 (4)	0.8321 (7)	0.6037 (5)	0.0321 (15)
H3A	0.7289	0.8524	0.6023	0.039*
H3B	0.6578	0.8555	0.6654	0.039*
C11	0.4818 (4)	0.6210 (6)	0.3897 (5)	0.0203 (14)
C12	0.4303 (4)	0.6621 (6)	0.4717 (6)	0.0215 (14)
H12	0.4460	0.7218	0.5339	0.026*
C13	0.3597 (4)	0.6183 (6)	0.4632 (6)	0.0263 (15)
C14	0.3343 (5)	0.5289 (7)	0.3730 (7)	0.0297 (16)
H14	0.2849	0.4971	0.3675	0.036*
C15	0.3838 (5)	0.4888 (6)	0.2927 (7)	0.0284 (16)
H15	0.3678	0.4274	0.2322	0.034*
C16	0.4551 (4)	0.5343 (6)	0.2972 (6)	0.0223 (14)
O17	0.3070 (3)	0.6564 (5)	0.5375 (5)	0.0357 (13)
C17	0.3289 (5)	0.7586 (8)	0.6231 (7)	0.041 (2)
H17A	0.3686	0.7273	0.6817	0.062*
H17B	0.2863	0.7842	0.6659	0.062*
H17C	0.3466	0.8332	0.5796	0.062*
Br1A	0.99274 (5)	0.49736 (7)	0.65777 (6)	0.0360 (4)
C1A	1.0400 (4)	0.3329 (6)	0.9065 (5)	0.0226 (15)
O1A	1.0575 (3)	0.2699 (4)	1.0167 (4)	0.0203 (10)
C2A	1.1293 (4)	0.2357 (6)	1.0099 (5)	0.0200 (14)
N1A	1.0954 (4)	0.3361 (5)	0.8424 (5)	0.0244 (13)
N2A	1.1549 (3)	0.2720 (5)	0.9092 (5)	0.0228 (12)
N3A	1.1640 (4)	0.1696 (6)	1.1024 (5)	0.0270 (13)
H3A1	1.2103	0.1452	1.0994	0.032*
H3A2	1.1406	0.1507	1.1661	0.032*
C11A	0.9651 (5)	0.3856 (6)	0.8901 (6)	0.0260 (16)
C12A	0.9172 (4)	0.3643 (6)	0.9829 (6)	0.0239 (15)
H12A	0.9336	0.3111	1.0498	0.029*
C13A	0.8485 (4)	0.4180 (7)	0.9782 (6)	0.0282 (16)
C14A	0.8216 (5)	0.4928 (7)	0.8771 (7)	0.0295 (16)
H14A	0.7734	0.5294	0.8727	0.035*
C15A	0.8662 (5)	0.5116 (6)	0.7854 (6)	0.0274 (17)
H15A	0.8483	0.5613	0.7169	0.033*
C16A	0.9366 (4)	0.4601 (6)	0.7902 (6)	0.0236 (15)
O17A	0.7997 (3)	0.4066 (6)	1.0652 (5)	0.0391 (14)
C17A	0.8242 (6)	0.3319 (13)	1.1703 (9)	0.068 (3)
H17D	0.8330	0.2425	1.1463	0.101*
H17E	0.7861	0.3334	1.2275	0.101*
H17F	0.8702	0.3688	1.2090	0.101*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
Br1	0.0523 (7)	0.0372 (5)	0.0319 (5)	−0.0113 (4)	0.0139 (4)	−0.0169 (3)
C1	0.028 (4)	0.017 (3)	0.018 (3)	0.002 (3)	0.004 (3)	0.002 (2)
O1	0.024 (3)	0.024 (2)	0.015 (2)	0.001 (2)	0.0046 (17)	−0.0004 (16)
C2	0.038 (5)	0.026 (3)	0.017 (3)	0.000 (3)	0.007 (3)	0.005 (3)
N1	0.028 (4)	0.031 (3)	0.018 (3)	0.000 (3)	0.006 (2)	0.001 (2)
N2	0.023 (3)	0.035 (3)	0.018 (3)	−0.005 (3)	0.005 (2)	0.002 (2)
N3	0.021 (3)	0.050 (4)	0.027 (3)	−0.016 (3)	0.008 (2)	−0.013 (3)
C11	0.025 (4)	0.019 (3)	0.018 (3)	0.001 (3)	0.005 (3)	0.003 (2)
C12	0.020 (4)	0.020 (3)	0.024 (3)	−0.003 (3)	0.002 (3)	−0.003 (2)
C13	0.026 (4)	0.022 (3)	0.032 (3)	−0.001 (3)	0.010 (3)	0.001 (3)
C14	0.032 (5)	0.022 (3)	0.034 (4)	−0.005 (3)	0.002 (3)	0.008 (3)
C15	0.032 (5)	0.019 (3)	0.032 (4)	−0.005 (3)	−0.006 (3)	0.002 (3)
C16	0.030 (4)	0.017 (3)	0.020 (3)	−0.001 (3)	0.005 (3)	0.002 (2)
O17	0.021 (3)	0.039 (3)	0.048 (3)	−0.001 (2)	0.009 (2)	−0.008 (2)
C17	0.047 (6)	0.038 (4)	0.041 (4)	0.002 (4)	0.014 (4)	−0.014 (3)
Br1A	0.0476 (6)	0.0419 (5)	0.0202 (4)	0.0179 (4)	0.0126 (3)	0.0108 (3)
C1A	0.039 (4)	0.016 (3)	0.012 (3)	−0.001 (3)	0.002 (3)	−0.001 (2)
O1A	0.023 (3)	0.022 (2)	0.017 (2)	0.002 (2)	0.0069 (17)	0.0016 (17)
C2A	0.029 (4)	0.017 (3)	0.015 (3)	−0.001 (3)	0.004 (2)	−0.002 (2)
N1A	0.033 (4)	0.025 (3)	0.017 (3)	0.001 (3)	0.011 (2)	0.002 (2)
N2A	0.023 (3)	0.026 (3)	0.020 (3)	0.003 (2)	0.006 (2)	0.002 (2)
N3A	0.029 (4)	0.032 (3)	0.020 (3)	0.006 (3)	0.007 (2)	0.005 (2)
C11A	0.046 (5)	0.014 (3)	0.019 (3)	−0.005 (3)	0.009 (3)	−0.003 (2)
C12A	0.020 (4)	0.023 (3)	0.029 (3)	−0.001 (3)	0.003 (3)	0.007 (3)
C13A	0.024 (4)	0.029 (4)	0.032 (4)	−0.003 (3)	0.006 (3)	0.005 (3)
C14A	0.027 (4)	0.024 (3)	0.037 (4)	−0.001 (3)	0.002 (3)	0.001 (3)
C15A	0.043 (5)	0.016 (3)	0.023 (3)	0.000 (3)	−0.001 (3)	−0.003 (2)
C16A	0.033 (4)	0.019 (3)	0.020 (3)	0.006 (3)	0.008 (3)	−0.002 (2)
O17A	0.024 (3)	0.052 (3)	0.043 (3)	0.008 (3)	0.014 (2)	0.021 (3)
C17A	0.048 (6)	0.106 (9)	0.053 (6)	0.013 (6)	0.026 (5)	0.043 (6)

Geometric parameters (Å, º)

Br1—C16	1.895 (7)	Br1A—C16A	1.903 (7)
C1—N1	1.295 (9)	C1A—N1A	1.283 (9)
C1—O1	1.393 (7)	C1A—O1A	1.396 (7)
C1—C11	1.452 (10)	C1A—C11A	1.460 (11)
O1—C2	1.361 (9)	O1A—C2A	1.359 (8)
C2—N2	1.308 (9)	C2A—N2A	1.304 (8)
C2—N3	1.334 (9)	C2A—N3A	1.342 (8)
N1—N2	1.420 (9)	N1A—N2A	1.418 (8)
N3—H3A	0.8800	N3A—H3A1	0.8800
N3—H3B	0.8800	N3A—H3A2	0.8800
C11—C16	1.414 (9)	C11A—C16A	1.408 (9)
C11—C12	1.429 (9)	C11A—C12A	1.425 (10)
C12—C13	1.354 (10)	C12A—C13A	1.362 (11)
C12—H12	0.9500	C12A—H12A	0.9500
C13—O17	1.376 (9)	C13A—O17A	1.375 (9)
C13—C14	1.409 (10)	C13A—C14A	1.413 (10)
C14—C15	1.386 (12)	C14A—C15A	1.371 (11)
C14—H14	0.9500	C14A—H14A	0.9500
C15—C16	1.374 (11)	C15A—C16A	1.382 (11)
C15—H15	0.9500	C15A—H15A	0.9500
O17—C17	1.453 (9)	O17A—C17A	1.436 (10)
C17—H17A	0.9800	C17A—H17D	0.9800
C17—H17B	0.9800	C17A—H17E	0.9800
C17—H17C	0.9800	C17A—H17F	0.9800
N1—C1—O1	111.2 (6)	N1A—C1A—O1A	111.8 (6)
N1—C1—C11	133.5 (6)	N1A—C1A—C11A	133.5 (6)
O1—C1—C11	115.3 (6)	O1A—C1A—C11A	114.7 (6)
C2—O1—C1	103.1 (5)	C2A—O1A—C1A	102.4 (5)
N2—C2—N3	128.3 (7)	N2A—C2A—N3A	128.5 (7)
N2—C2—O1	112.8 (6)	N2A—C2A—O1A	113.1 (6)
N3—C2—O1	119.0 (6)	N3A—C2A—O1A	118.4 (6)
C1—N1—N2	107.4 (5)	C1A—N1A—N2A	107.3 (5)
C2—N2—N1	105.6 (6)	C2A—N2A—N1A	105.5 (6)
C2—N3—H3A	120.0	C2A—N3A—H3A1	120.0
C2—N3—H3B	120.0	C2A—N3A—H3A2	120.0
H3A—N3—H3B	120.0	H3A1—N3A—H3A2	120.0
C16—C11—C12	116.8 (7)	C16A—C11A—C12A	116.7 (7)
C16—C11—C1	125.1 (6)	C16A—C11A—C1A	124.9 (6)
C12—C11—C1	118.1 (6)	C12A—C11A—C1A	118.4 (6)
C13—C12—C11	121.8 (6)	C13A—C12A—C11A	121.8 (6)
C13—C12—H12	119.1	C13A—C12A—H12A	119.1
C11—C12—H12	119.1	C11A—C12A—H12A	119.1
C12—C13—O17	124.6 (6)	C12A—C13A—O17A	125.8 (6)
C12—C13—C14	121.0 (7)	C12A—C13A—C14A	120.2 (7)
O17—C13—C14	114.4 (7)	O17A—C13A—C14A	114.0 (7)
C15—C14—C13	117.6 (8)	C15A—C14A—C13A	118.8 (8)
C15—C14—H14	121.2	C15A—C14A—H14A	120.6
C13—C14—H14	121.2	C13A—C14A—H14A	120.6
C16—C15—C14	122.6 (7)	C14A—C15A—C16A	121.6 (7)
C16—C15—H15	118.7	C14A—C15A—H15A	119.2
C14—C15—H15	118.7	C16A—C15A—H15A	119.2
C15—C16—C11	120.2 (7)	C15A—C16A—C11A	120.9 (7)
C15—C16—Br1	117.6 (5)	C15A—C16A—Br1A	116.8 (5)
C11—C16—Br1	122.2 (6)	C11A—C16A—Br1A	122.3 (6)
C13—O17—C17	115.9 (6)	C13A—O17A—C17A	116.4 (7)
O17—C17—H17A	109.5	O17A—C17A—H17D	109.5
O17—C17—H17B	109.5	O17A—C17A—H17E	109.5
H17A—C17—H17B	109.5	H17D—C17A—H17E	109.5
O17—C17—H17C	109.5	O17A—C17A—H17F	109.5
H17A—C17—H17C	109.5	H17D—C17A—H17F	109.5
H17B—C17—H17C	109.5	H17E—C17A—H17F	109.5
N1—C1—O1—C2	−1.2 (7)	N1A—C1A—O1A—C2A	−0.4 (7)
C11—C1—O1—C2	178.4 (5)	C11A—C1A—O1A—C2A	−177.9 (5)
C1—O1—C2—N2	1.1 (7)	C1A—O1A—C2A—N2A	0.2 (7)
C1—O1—C2—N3	−179.6 (6)	C1A—O1A—C2A—N3A	−178.8 (6)
O1—C1—N1—N2	1.0 (7)	O1A—C1A—N1A—N2A	0.4 (7)
C11—C1—N1—N2	−178.6 (6)	C11A—C1A—N1A—N2A	177.2 (7)
N3—C2—N2—N1	−179.8 (7)	N3A—C2A—N2A—N1A	178.9 (6)
O1—C2—N2—N1	−0.5 (7)	O1A—C2A—N2A—N1A	0.0 (7)
C1—N1—N2—C2	−0.3 (7)	C1A—N1A—N2A—C2A	−0.2 (7)
N1—C1—C11—C16	8.9 (11)	N1A—C1A—C11A—C16A	−1.1 (12)
O1—C1—C11—C16	−170.6 (6)	O1A—C1A—C11A—C16A	175.7 (6)
N1—C1—C11—C12	−172.5 (7)	N1A—C1A—C11A—C12A	−179.2 (7)
O1—C1—C11—C12	7.9 (8)	O1A—C1A—C11A—C12A	−2.4 (8)
C16—C11—C12—C13	1.4 (9)	C16A—C11A—C12A—C13A	−3.0 (10)
C1—C11—C12—C13	−177.2 (6)	C1A—C11A—C12A—C13A	175.3 (6)
C11—C12—C13—O17	−178.4 (6)	C11A—C12A—C13A—O17A	−177.6 (7)
C11—C12—C13—C14	0.6 (10)	C11A—C12A—C13A—C14A	2.8 (11)
C12—C13—C14—C15	−0.8 (10)	C12A—C13A—C14A—C15A	−1.0 (11)
O17—C13—C14—C15	178.3 (6)	O17A—C13A—C14A—C15A	179.3 (6)
C13—C14—C15—C16	−1.0 (10)	C13A—C14A—C15A—C16A	−0.4 (11)
C14—C15—C16—C11	3.1 (10)	C14A—C15A—C16A—C11A	0.2 (10)
C14—C15—C16—Br1	−177.6 (5)	C14A—C15A—C16A—Br1A	−178.7 (5)
C12—C11—C16—C15	−3.1 (9)	C12A—C11A—C16A—C15A	1.5 (10)
C1—C11—C16—C15	175.4 (6)	C1A—C11A—C16A—C15A	−176.6 (6)
C12—C11—C16—Br1	177.6 (5)	C12A—C11A—C16A—Br1A	−179.7 (5)
C1—C11—C16—Br1	−3.9 (9)	C1A—C11A—C16A—Br1A	2.2 (9)
C12—C13—O17—C17	5.3 (10)	C12A—C13A—O17A—C17A	0.5 (12)
C14—C13—O17—C17	−173.7 (6)	C14A—C13A—O17A—C17A	−179.8 (8)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
N3—H3A···N2A^i	0.88	2.28	3.043 (9)	145
N3—H3B···N1^ii	0.88	2.24	3.067 (8)	158
N3A—H3A1···N2^iii	0.88	2.27	3.015 (9)	142
N3A—H3A2···N1A^iv	0.88	2.19	3.043 (8)	162

Symmetry codes: (i) −x+2, y+1/2, −z+3/2; (ii) x, −y+3/2, z+1/2; (iii) −x+2, y−1/2, −z+3/2; (iv) x, −y+1/2, z+1/2.