5-[5-(4-Chloro­phen­yl)isoxazol-3-yl]-N-phenyl-1,3,4-oxa­diazol-2-amine

The title compound, C₁₇H₁₁ClN₄O₂, consists of chloro­phenyl (A), isoxazolyl (B), oxa­diazolyl (C) and phenyl (D) rings with twist angles between the planes through neighbouring rings A/B, B/C and C/D of 14.9 (1), 1.8 (1) and 8.9 (1)° respectively. In the crystal, adjacent mol­ecules related by inversion symmetry form columns parallel to the [010] direction through π–π stacking [shortest centroid–centroid separation = 3.6203 (10) Å]; these are cross-linked by N—H...N inter­actions in the [001] direction.

Key indicators

• Single-crystal X-ray study
• T = 296 K
• Mean [sigma](C-C) = 0.003 Å
• R factor = 0.045
• wR factor = 0.112
• Data-to-parameter ratio = 17.1

checkCIF/PLATON results

No syntax errors found



Datablock: I


Alert level C
PLAT906_ALERT_3_C Large K Value in the Analysis of Variance ......      2.144 Check

Alert level G
PLAT007_ALERT_5_G Number of Unrefined Donor-H Atoms ..............          1 Report
PLAT395_ALERT_2_G Deviating  X-O-Y    Angle From 120 for O1             109.3 Degree
PLAT398_ALERT_2_G Deviating  C-O-C    Angle From 120 for O2             102.0 Degree
PLAT802_ALERT_4_G CIF Input Record(s) with more than 80 Characters          1 Info
PLAT910_ALERT_3_G Missing # of FCF Reflection(s) Below Theta(Min).          2 Note
PLAT912_ALERT_4_G Missing # of FCF Reflections Above STh/L=  0.600        549 Note
PLAT978_ALERT_2_G Number C-C Bonds with Positive Residual Density.         10 Info

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

   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
   2 ALERT type 4 Improvement, methodology, query or suggestion
   1 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.

   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: CrysAlis PRO (Rigaku OD, 2015); cell refinement: CrysAlis PRO (Rigaku OD, 2015); data reduction: CrysAlis PRO (Rigaku OD, 2015); program(s) used to solve structure: SHELXS (Sheldrick, 2008); program(s) used to refine structure: SHELXL2018 (Sheldrick, 2015); molecular graphics: ORTEP-3 for Windows and WinGX (Farrugia, 2012); software used to prepare material for publication: CHEMDRAW Ultra (Cambridge Soft, 2001).

5-[5-(4-Chlorophenyl)isoxazol-3-yl]-N-phenyl-1,3,4-oxadiazol-2-amine

Crystal data

C17H11ClN4O2	F(000) = 696
Mr = 338.75	Dx = 1.508 Mg m^−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
a = 17.8925 (15) Å	Cell parameters from 3445 reflections
b = 7.4168 (6) Å	θ = 3.3–26.7°
c = 11.5006 (9) Å	µ = 0.27 mm^−1
β = 102.061 (8)°	T = 296 K
V = 1492.5 (2) Å^3	Plate, colourless
Z = 4	0.32 × 0.17 × 0.04 mm

Data collection

Rigaku Oxford Diffraction SuperNova, Dual, Cu at zero, Atlas diffractometer	2622 reflections with I > 2σ(I)
ω scans	Rint = 0.027
Absorption correction: gaussian (CrysAlisPro; Rigaku OD, 2015)	θmax = 29.8°, θmin = 3.0°
Tmin = 0.768, Tmax = 1.000	h = −24→23
13114 measured reflections	k = −10→10
3720 independent reflections	l = −13→16

Refinement

Refinement on F^2	Hydrogen site location: inferred from neighbouring sites
Least-squares matrix: full	H-atom parameters constrained
R[F^2 > 2σ(F^2)] = 0.045	w = 1/[σ^2(Fo^2) + (0.039P)^2 + 0.4804P] where P = (Fo^2 + 2Fc^2)/3
wR(F^2) = 0.112	(Δ/σ)max < 0.001
S = 1.06	Δρmax = 0.25 e Å^−3
3720 reflections	Δρmin = −0.23 e Å^−3
218 parameters	Extinction correction: SHELXL-2018/1 (Sheldrick 2018), Fc^*=kFc[1+0.001xFc^2λ^3/sin(2θ)]^-1/4
0 restraints	Extinction coefficient: 0.0044 (7)
Primary atom site location: structure-invariant direct methods

Special details

Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes.

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

	x	y	z	Uiso*/Ueq
C1	0.27509 (9)	0.6433 (2)	0.57408 (14)	0.0354 (4)
C2	0.27554 (10)	0.5711 (2)	0.68585 (14)	0.0380 (4)
H2	0.321696	0.540461	0.735750	0.046*
C3	0.20791 (11)	0.5447 (2)	0.72307 (15)	0.0406 (4)
H3	0.208175	0.496146	0.797718	0.049*
C4	0.13988 (10)	0.5911 (2)	0.64829 (16)	0.0419 (4)
C5	0.13775 (10)	0.6597 (3)	0.53621 (16)	0.0443 (4)
H5	0.091345	0.687890	0.486141	0.053*
C6	0.20539 (10)	0.6856 (2)	0.49975 (15)	0.0410 (4)
H6	0.204587	0.732140	0.424398	0.049*
C7	0.34717 (10)	0.6763 (2)	0.53732 (14)	0.0368 (4)
C8	0.42112 (10)	0.6850 (2)	0.59279 (15)	0.0411 (4)
H8	0.441861	0.666766	0.673050	0.049*
C9	0.45996 (10)	0.7280 (2)	0.50222 (15)	0.0395 (4)
C10	0.54121 (10)	0.7559 (2)	0.50955 (14)	0.0386 (4)
C11	0.64134 (9)	0.8153 (2)	0.44570 (14)	0.0363 (4)
C12	0.76067 (9)	0.8721 (2)	0.37782 (14)	0.0348 (4)
C13	0.78904 (10)	0.9338 (2)	0.28169 (15)	0.0416 (4)
H13	0.755572	0.967507	0.211870	0.050*
C14	0.86646 (11)	0.9450 (3)	0.28962 (17)	0.0480 (5)
H14	0.885249	0.984768	0.224560	0.058*
C15	0.91682 (11)	0.8977 (3)	0.39347 (17)	0.0494 (5)
H15	0.969268	0.906781	0.398840	0.059*
C16	0.88857 (10)	0.8372 (3)	0.48854 (17)	0.0473 (5)
H16	0.922266	0.805371	0.558565	0.057*
C17	0.81049 (10)	0.8229 (2)	0.48169 (15)	0.0392 (4)
H17	0.791856	0.780592	0.546287	0.047*
N1	0.41386 (9)	0.7429 (3)	0.39846 (14)	0.0606 (5)
N2	0.59647 (9)	0.7436 (2)	0.59928 (13)	0.0490 (4)
N3	0.66384 (8)	0.7833 (2)	0.55885 (13)	0.0487 (4)
N4	0.68044 (8)	0.8585 (2)	0.36244 (12)	0.0405 (4)
H4	0.654043	0.880249	0.292363	0.049*
O1	0.34130 (7)	0.7092 (2)	0.42024 (11)	0.0600 (4)
O2	0.56429 (6)	0.80070 (17)	0.40728 (10)	0.0409 (3)
Cl1	0.05523 (3)	0.56575 (9)	0.69766 (5)	0.0682 (2)

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
C1	0.0365 (9)	0.0360 (9)	0.0339 (8)	−0.0021 (7)	0.0078 (7)	−0.0019 (7)
C2	0.0399 (9)	0.0403 (9)	0.0324 (8)	−0.0005 (7)	0.0046 (7)	−0.0025 (7)
C3	0.0490 (11)	0.0427 (10)	0.0317 (8)	−0.0024 (8)	0.0119 (7)	−0.0009 (8)
C4	0.0389 (10)	0.0444 (10)	0.0465 (10)	−0.0004 (8)	0.0178 (8)	−0.0048 (8)
C5	0.0372 (10)	0.0494 (11)	0.0455 (10)	0.0037 (8)	0.0069 (8)	0.0012 (9)
C6	0.0422 (10)	0.0467 (10)	0.0344 (9)	0.0018 (8)	0.0088 (7)	0.0054 (8)
C7	0.0375 (9)	0.0409 (9)	0.0315 (8)	−0.0010 (7)	0.0061 (7)	0.0015 (7)
C8	0.0373 (9)	0.0538 (11)	0.0316 (8)	−0.0017 (8)	0.0062 (7)	−0.0005 (8)
C9	0.0346 (9)	0.0462 (10)	0.0373 (9)	−0.0011 (8)	0.0068 (7)	0.0013 (8)
C10	0.0348 (9)	0.0480 (10)	0.0338 (8)	−0.0012 (8)	0.0087 (7)	0.0001 (8)
C11	0.0288 (8)	0.0430 (9)	0.0362 (9)	0.0006 (7)	0.0046 (7)	−0.0043 (7)
C12	0.0326 (9)	0.0356 (9)	0.0357 (8)	−0.0002 (7)	0.0063 (7)	−0.0050 (7)
C13	0.0367 (9)	0.0515 (11)	0.0355 (9)	−0.0013 (8)	0.0049 (7)	0.0017 (8)
C14	0.0435 (11)	0.0560 (12)	0.0471 (11)	−0.0051 (9)	0.0154 (8)	0.0002 (9)
C15	0.0327 (9)	0.0614 (12)	0.0544 (11)	−0.0017 (9)	0.0101 (8)	−0.0043 (10)
C16	0.0372 (10)	0.0564 (12)	0.0443 (10)	0.0034 (9)	−0.0003 (8)	−0.0018 (9)
C17	0.0380 (9)	0.0444 (10)	0.0344 (9)	0.0005 (8)	0.0059 (7)	−0.0010 (8)
N1	0.0337 (9)	0.1058 (15)	0.0422 (9)	−0.0077 (9)	0.0076 (7)	0.0204 (9)
N2	0.0364 (8)	0.0768 (12)	0.0341 (8)	−0.0046 (8)	0.0084 (6)	0.0010 (8)
N3	0.0349 (8)	0.0784 (12)	0.0323 (8)	−0.0047 (8)	0.0059 (6)	−0.0001 (8)
N4	0.0304 (7)	0.0583 (9)	0.0316 (7)	0.0004 (7)	0.0035 (6)	0.0050 (7)
O1	0.0337 (7)	0.1065 (12)	0.0386 (7)	−0.0082 (7)	0.0048 (5)	0.0204 (7)
O2	0.0308 (6)	0.0564 (8)	0.0345 (6)	−0.0015 (5)	0.0050 (5)	0.0041 (6)
Cl1	0.0494 (3)	0.0880 (4)	0.0766 (4)	0.0034 (3)	0.0345 (3)	0.0077 (3)

Geometric parameters (Å, º)

C1—C2	1.391 (2)	C10—O2	1.3665 (19)
C1—C6	1.393 (2)	C11—N3	1.301 (2)
C1—C7	1.459 (2)	C11—N4	1.338 (2)
C2—C3	1.379 (2)	C11—O2	1.3611 (19)
C2—H2	0.9300	C12—C17	1.382 (2)
C3—C4	1.379 (3)	C12—C13	1.387 (2)
C3—H3	0.9300	C12—N4	1.413 (2)
C4—C5	1.379 (3)	C13—C14	1.372 (3)
C4—Cl1	1.7351 (18)	C13—H13	0.9300
C5—C6	1.375 (2)	C14—C15	1.383 (3)
C5—H5	0.9300	C14—H14	0.9300
C6—H6	0.9300	C15—C16	1.372 (3)
C7—C8	1.345 (2)	C15—H15	0.9300
C7—O1	1.351 (2)	C16—C17	1.387 (2)
C8—C9	1.404 (2)	C16—H16	0.9300
C8—H8	0.9300	C17—H17	0.9300
C9—N1	1.306 (2)	N1—O1	1.3952 (19)
C9—C10	1.453 (2)	N2—N3	1.411 (2)
C10—N2	1.275 (2)	N4—H4	0.8600
C2—C1—C6	119.05 (16)	N3—C11—N4	131.36 (16)
C2—C1—C7	119.83 (15)	N3—C11—O2	113.02 (15)
C6—C1—C7	121.11 (15)	N4—C11—O2	115.62 (14)
C3—C2—C1	120.36 (16)	C17—C12—C13	119.92 (16)
C3—C2—H2	119.8	C17—C12—N4	122.98 (15)
C1—C2—H2	119.8	C13—C12—N4	117.08 (15)
C4—C3—C2	119.23 (16)	C14—C13—C12	119.99 (17)
C4—C3—H3	120.4	C14—C13—H13	120.0
C2—C3—H3	120.4	C12—C13—H13	120.0
C5—C4—C3	121.56 (16)	C13—C14—C15	120.58 (18)
C5—C4—Cl1	119.36 (14)	C13—C14—H14	119.7
C3—C4—Cl1	119.07 (14)	C15—C14—H14	119.7
C6—C5—C4	118.86 (17)	C16—C15—C14	119.29 (17)
C6—C5—H5	120.6	C16—C15—H15	120.4
C4—C5—H5	120.6	C14—C15—H15	120.4
C5—C6—C1	120.92 (16)	C15—C16—C17	120.94 (17)
C5—C6—H6	119.5	C15—C16—H16	119.5
C1—C6—H6	119.5	C17—C16—H16	119.5
C8—C7—O1	109.14 (15)	C12—C17—C16	119.28 (16)
C8—C7—C1	135.40 (16)	C12—C17—H17	120.4
O1—C7—C1	115.45 (14)	C16—C17—H17	120.4
C7—C8—C9	104.44 (15)	C9—N1—O1	104.75 (14)
C7—C8—H8	127.8	C10—N2—N3	106.85 (14)
C9—C8—H8	127.8	C11—N3—N2	105.10 (13)
N1—C9—C8	112.40 (16)	C11—N4—C12	126.68 (14)
N1—C9—C10	118.31 (15)	C11—N4—H4	116.7
C8—C9—C10	129.29 (16)	C12—N4—H4	116.7
N2—C10—O2	113.04 (15)	C7—O1—N1	109.26 (13)
N2—C10—C9	129.36 (16)	C11—O2—C10	101.99 (13)
O2—C10—C9	117.60 (14)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
C17—H17···N3	0.93	2.33	2.955 (2)	125
N4—H4···N2^i	0.86	2.42	3.176 (2)	146

Symmetry code: (i) x, −y+3/2, z−1/2.