5-(4-Meth­oxy­phen­yl)-1,3,4-oxa­diazol-2-amine

In the title compound, C₉H₉N₃O₂, the dihedral angle between the aromatic rings is 8.64 (10)°. The crystal structure features inversion-related dimers linked by pairs of N—H...N hydrogen bonds, generating R₂²(8) loops. A further N—H...N hydrogen bond links the dimers into (100) sheets.

Key indicators

• Single-crystal X-ray study
• T = 296 K
• Mean [sigma](C-C) = 0.003 Å
• R factor = 0.046
• wR factor = 0.142
• Data-to-parameter ratio = 11.1

checkCIF/PLATON results

No syntax errors found



Alert level C
THETM01_ALERT_3_C  The value of sine(theta_max)/wavelength is less than 0.590
            Calculated sin(theta_max)/wavelength =    0.5868
PLAT029_ALERT_3_C _diffrn_measured_fraction_theta_full value Low .      0.975 Note
PLAT911_ALERT_3_C Missing # FCF Refl Between THmin & STh/L=  0.587         33 Report
PLAT934_ALERT_3_C Number of (Iobs-Icalc)/SigmaW > 10 Outliers ....          1 Check

Alert level G
PLAT005_ALERT_5_G No Embedded Refinement Details found  in the CIF     Please Do !
PLAT007_ALERT_5_G Number of Unrefined Donor-H Atoms ..............          2 Report
PLAT093_ALERT_1_G No s.u.'s on H-positions, Refinement Reported as      mixed Check
PLAT909_ALERT_3_G Percentage of Observed Data at Theta(Max) Still          71 %
PLAT910_ALERT_3_G Missing # of FCF Reflection(s) Below Theta(Min)           2 Note
PLAT978_ALERT_2_G Number C-C Bonds with Positive Residual Density           1 Note

   0 ALERT level A = Most likely a serious problem - resolve or explain
   0 ALERT level B = A potentially serious problem, consider carefully
   4 ALERT level C = Check. Ensure it is not caused by an omission or oversight
   6 ALERT level G = General information/check it is not something unexpected

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


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.

Author Response: ... All the authors have equal contributions to this work. NS -- Data collection and processing NP -- Synthesis Zabi-- Designed the synthesis HRM -- Spectroscopic Studies SAK -- Crystallization NKL -- Final analysis, write up and Corresponding author IW -- Solved and analyzed the structure and Corresponding Author

   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

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Computing details

Data collection: APEX2 (Bruker, 2013); cell refinement: SAINT (Bruker, 2013); data reduction: SAINT (Bruker, 2013); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: Mercury (Macrae et al., 2008); software used to prepare material for publication: Mercury (Macrae et al., 2008).

5-(4-Methoxyphenyl)-1,3,4-oxadiazol-2-amine

Crystal data

C9H9N3O2	F(000) = 400
Mr = 191.19	Dx = 1.463 Mg m^−3
Monoclinic, P21/c	Cu Kα radiation, λ = 1.54178 Å
Hall symbol: -P 2ybc	Cell parameters from 1308 reflections
a = 16.2029 (9) Å	θ = 8.0–64.8°
b = 5.0730 (3) Å	µ = 0.90 mm^−1
c = 11.1133 (6) Å	T = 296 K
β = 108.096 (3)°	Block, colourless
V = 868.30 (9) Å^3	0.28 × 0.26 × 0.23 mm
Z = 4

Data collection

Bruker X8 Proteum diffractometer	1430 independent reflections
Radiation source: Bruker MicroStar microfocus rotating anode	1308 reflections with I > 2σ(I)
Helios multilayer optics monochromator	Rint = 0.042
Detector resolution: 18.4 pixels mm^-1	θmax = 64.8°, θmin = 8.0°
φ and ω scans	h = −18→18
Absorption correction: multi-scan (SADABS; Bruker, 2013)	k = −5→5
Tmin = 0.788, Tmax = 0.821	l = −12→12
5230 measured reflections

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)] = 0.046	H atoms treated by a mixture of independent and constrained refinement
wR(F^2) = 0.142	w = 1/[σ^2(Fo^2) + (0.0816P)^2 + 0.4652P] where P = (Fo^2 + 2Fc^2)/3
S = 1.15	(Δ/σ)max < 0.001
1430 reflections	Δρmax = 0.32 e Å^−3
129 parameters	Δρmin = −0.31 e Å^−3
0 restraints	Extinction correction: SHELXL97 (Sheldrick, 2008), FC^*=KFC[1+0.001XFC^2Λ^3/SIN(2Θ)]^-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.0050 (13)

Special details

Geometry. Bond distances, angles etc. have been calculated using the rounded fractional coordinates. All su's are estimated from the variances of the (full) variance-covariance matrix. The cell esds are taken into account in the estimation of distances, angles and torsion angles

Refinement. Refinement on F² for ALL reflections except those flagged by the user for potential systematic errors. Weighted R-factors wR and all goodnesses of fit S are based on F², conventional R-factors R are based on F, with F set to zero for negative F². The observed criterion of F² > 2sigma(F²) is used only for calculating -R-factor-obs 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.

H atoms were fixed geometrically (C—H = 0.93–0.96 Å) and allowed to ride on their parent atoms with U_iso(H) = 1.5U_eq(C) for the methyl H atoms and = 1.2U_eq(C) for the others.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Ų)

	x	y	z	Uiso*/Ueq
O1	0.84349 (8)	1.0817 (3)	0.83232 (11)	0.0197 (4)
O2	0.58911 (9)	0.4726 (3)	0.65817 (13)	0.0230 (4)
N1	0.88643 (10)	1.0232 (3)	1.03973 (15)	0.0186 (5)
N2	0.93522 (10)	1.2299 (3)	1.01268 (14)	0.0190 (5)
N3	0.93358 (12)	1.4284 (4)	0.81916 (15)	0.0264 (6)
C1	0.90787 (12)	1.2572 (4)	0.88958 (17)	0.0183 (6)
C2	0.83441 (12)	0.9410 (4)	0.93398 (17)	0.0164 (6)
C3	0.76937 (12)	0.7335 (4)	0.91245 (17)	0.0186 (6)
C4	0.70870 (12)	0.6920 (4)	0.79427 (17)	0.0178 (6)
C5	0.64685 (12)	0.4939 (4)	0.77827 (18)	0.0190 (6)
C6	0.64528 (13)	0.3346 (4)	0.87986 (19)	0.0217 (6)
C7	0.70707 (13)	0.3786 (4)	0.99784 (18)	0.0223 (6)
C8	0.76843 (12)	0.5742 (4)	1.01542 (18)	0.0196 (6)
C9	0.52835 (14)	0.2595 (4)	0.6353 (2)	0.0267 (7)
H3A	0.97340	1.54120	0.85420	0.0320*
H3B	0.91050	1.42720	0.73820	0.0320*
H4	0.70950	0.79660	0.72590	0.0210*
H6	0.60400	0.20200	0.86940	0.0260*
H7	0.70660	0.27310	1.06610	0.0270*
H8	0.80890	0.60070	1.09470	0.0230*
H9A	0.55920	0.09510	0.65060	0.0400*
H9B	0.49150	0.26560	0.54900	0.0400*
H9C	0.49360	0.27480	0.69090	0.0400*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
O1	0.0222 (7)	0.0219 (8)	0.0132 (7)	−0.0060 (6)	0.0029 (5)	−0.0003 (5)
O2	0.0206 (8)	0.0251 (8)	0.0201 (7)	−0.0072 (6)	0.0016 (6)	−0.0015 (6)
N1	0.0196 (9)	0.0198 (9)	0.0157 (8)	−0.0016 (7)	0.0045 (7)	0.0003 (6)
N2	0.0197 (9)	0.0217 (9)	0.0149 (8)	−0.0040 (7)	0.0042 (6)	0.0002 (6)
N3	0.0309 (10)	0.0317 (11)	0.0131 (8)	−0.0154 (8)	0.0017 (7)	0.0001 (7)
C1	0.0177 (10)	0.0206 (11)	0.0151 (9)	−0.0029 (8)	0.0030 (7)	−0.0026 (7)
C2	0.0186 (10)	0.0176 (10)	0.0132 (9)	0.0007 (8)	0.0053 (7)	0.0016 (7)
C3	0.0193 (10)	0.0191 (11)	0.0178 (10)	0.0023 (8)	0.0065 (8)	−0.0003 (7)
C4	0.0199 (10)	0.0183 (11)	0.0161 (9)	−0.0009 (8)	0.0069 (8)	0.0016 (8)
C5	0.0192 (10)	0.0197 (11)	0.0176 (10)	0.0028 (8)	0.0050 (8)	−0.0025 (8)
C6	0.0208 (10)	0.0202 (11)	0.0254 (11)	−0.0012 (8)	0.0089 (8)	−0.0004 (8)
C7	0.0261 (11)	0.0212 (11)	0.0215 (10)	0.0033 (8)	0.0103 (8)	0.0047 (8)
C8	0.0199 (10)	0.0216 (11)	0.0172 (10)	0.0031 (8)	0.0058 (8)	0.0007 (8)
C9	0.0256 (11)	0.0225 (12)	0.0288 (11)	−0.0055 (9)	0.0039 (9)	−0.0034 (8)

Geometric parameters (Å, º)

O1—C1	1.369 (2)	C3—C4	1.391 (3)
O1—C2	1.382 (2)	C4—C5	1.391 (3)
O2—C5	1.376 (2)	C5—C6	1.395 (3)
O2—C9	1.431 (3)	C6—C7	1.399 (3)
N1—N2	1.401 (2)	C7—C8	1.375 (3)
N1—C2	1.285 (2)	C4—H4	0.9300
N2—C1	1.308 (2)	C6—H6	0.9300
N3—C1	1.320 (3)	C7—H7	0.9300
N3—H3A	0.8600	C8—H8	0.9300
N3—H3B	0.8600	C9—H9A	0.9600
C2—C3	1.456 (3)	C9—H9B	0.9600
C3—C8	1.405 (3)	C9—H9C	0.9600
C1—O1—C2	102.42 (14)	O2—C5—C6	124.18 (18)
C5—O2—C9	117.05 (16)	C5—C6—C7	118.59 (19)
N2—N1—C2	107.48 (15)	C6—C7—C8	121.59 (18)
N1—N2—C1	105.86 (15)	C3—C8—C7	119.32 (18)
H3A—N3—H3B	120.00	C3—C4—H4	120.00
C1—N3—H3A	120.00	C5—C4—H4	120.00
C1—N3—H3B	120.00	C5—C6—H6	121.00
O1—C1—N2	112.28 (17)	C7—C6—H6	121.00
N2—C1—N3	128.53 (19)	C6—C7—H7	119.00
O1—C1—N3	119.18 (16)	C8—C7—H7	119.00
N1—C2—C3	128.38 (17)	C3—C8—H8	120.00
O1—C2—C3	119.63 (16)	C7—C8—H8	120.00
O1—C2—N1	111.96 (17)	O2—C9—H9A	109.00
C2—C3—C4	121.87 (17)	O2—C9—H9B	109.00
C2—C3—C8	118.20 (17)	O2—C9—H9C	109.00
C4—C3—C8	119.93 (18)	H9A—C9—H9B	109.00
C3—C4—C5	120.00 (18)	H9A—C9—H9C	109.00
C4—C5—C6	120.57 (18)	H9B—C9—H9C	109.00
O2—C5—C4	115.25 (17)
C2—O1—C1—N2	−0.4 (2)	N1—C2—C3—C4	170.2 (2)
C2—O1—C1—N3	−179.58 (19)	N1—C2—C3—C8	−9.3 (3)
C1—O1—C2—N1	0.5 (2)	C2—C3—C4—C5	−179.06 (19)
C1—O1—C2—C3	178.77 (18)	C8—C3—C4—C5	0.4 (3)
C9—O2—C5—C4	175.65 (18)	C2—C3—C8—C7	179.34 (19)
C9—O2—C5—C6	−5.1 (3)	C4—C3—C8—C7	−0.1 (3)
C2—N1—N2—C1	0.2 (2)	C3—C4—C5—O2	178.97 (18)
N2—N1—C2—O1	−0.5 (2)	C3—C4—C5—C6	−0.3 (3)
N2—N1—C2—C3	−178.51 (19)	O2—C5—C6—C7	−179.19 (19)
N1—N2—C1—O1	0.2 (2)	C4—C5—C6—C7	0.1 (3)
N1—N2—C1—N3	179.2 (2)	C5—C6—C7—C8	0.2 (3)
O1—C2—C3—C4	−7.8 (3)	C6—C7—C8—C3	−0.2 (3)
O1—C2—C3—C8	172.78 (18)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
N3—H3A···N2^i	0.86	2.09	2.924 (2)	163
N3—H3B···N1^ii	0.86	2.13	2.969 (2)	164

Symmetry codes: (i) −x+2, −y+3, −z+2; (ii) x, −y+5/2, z−1/2.