Crystal structure, Hirshfeld surface analysis and computational studies of 5-[(prop-2-en-1-yl)sulfan­yl]-1-[2-(tri­fluoro­meth­yl)phen­yl]-1H-tetra­zole

The title compound was synthesized from 2-(tri­fluoro­meth­yl)aniline by a multi-step reaction and is constructed from a pair of aromatic rings [2-(tri­fluoro­meth­yl)phenyl and tetra­zole], which are turned by 76.8 (1)° relative to each other because of significant steric hindrance of the tri­fluoro­methyl group at the ortho position of the benzene ring·In the crystal, very weak C—H...N and C—H...F hydrogen bonds and aromatic π–π stacking inter­actions link the mol­ecules into a three-dimensional network.

Key indicators

• Single-crystal X-ray study
• T = 150 K
• Mean [sigma](C-C) = 0.004 Å
• R factor = 0.035
• wR factor = 0.079
• Data-to-parameter ratio = 18.0

checkCIF/PLATON results

No syntax errors found



Datablock: I


Alert level C
PLAT340_ALERT_3_C Low Bond Precision on  C-C Bonds ...............    0.00433 Ang.
PLAT480_ALERT_4_C Long H...A H-Bond Reported H2B      ..N2       .       2.69 Ang.
PLAT480_ALERT_4_C Long H...A H-Bond Reported H3       ..F3       .       2.71 Ang.
PLAT480_ALERT_4_C Long H...A H-Bond Reported H4A      ..N3       .       2.67 Ang.
PLAT480_ALERT_4_C Long H...A H-Bond Reported H6       ..N4       .       2.76 Ang.
PLAT915_ALERT_3_C No Flack x Check Done: Low Friedel Pair Coverage         88 %

Alert level G
PLAT242_ALERT_2_G Low    'MainMol' Ueq as Compared to Neighbors of        C11 Check
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).          1 Note
PLAT912_ALERT_4_G Missing # of FCF Reflections Above STh/L=  0.600         57 Note
PLAT978_ALERT_2_G Number C-C Bonds with Positive Residual Density.          4 Info

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

   0 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
   3 ALERT type 3 Indicator that the structure quality may be low
   6 ALERT type 4 Improvement, methodology, query or suggestion
   0 ALERT type 5 Informative message, check

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Computing details

Data collection: CrysAlis PRO (Rigaku OD, 2018); cell refinement: CrysAlis PRO (Rigaku OD, 2018); data reduction: CrysAlis PRO (Rigaku OD, 2018); program(s) used to solve structure: SHELXT (Sheldrick, 2015a); program(s) used to refine structure: SHELXL (Sheldrick, 2015b); molecular graphics: OLEX2 (Dolomanov et al., 2009); software used to prepare material for publication: OLEX2 (Dolomanov et al., 2009).

5-[(Prop-2-en-1-yl)sulfanyl]-1-[2-(trifluoromethyl)phenyl]-1H-tetrazole

Crystal data

C11H9F3N4S	Dx = 1.504 Mg m^−3
Mr = 286.28	Mo Kα radiation, λ = 0.71073 Å
Orthorhombic, Pna21	Cell parameters from 9726 reflections
a = 7.6595 (3) Å	θ = 3.9–28.4°
b = 20.9841 (7) Å	µ = 0.28 mm^−1
c = 7.8641 (3) Å	T = 150 K
V = 1263.98 (8) Å^3	Block, colourless
Z = 4	0.35 × 0.24 × 0.15 mm
F(000) = 584

Data collection

Rigaku Oxford Diffraction New Gemini, Dual, Cu at home/near, Atlas diffractometer	2730 reflections with I > 2σ(I)
Detector resolution: 10.6426 pixels mm^-1	Rint = 0.059
ω scans	θmax = 28.9°, θmin = 2.8°
Absorption correction: analytical (CrysAlis PRO; Rigaku OD, 2018)	h = −10→10
Tmin = 0.929, Tmax = 0.969	k = −28→28
28170 measured reflections	l = −10→10
3094 independent reflections

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)] = 0.035	w = 1/[σ^2(Fo^2) + (0.0298P)^2 + 0.4395P] where P = (Fo^2 + 2Fc^2)/3
wR(F^2) = 0.079	(Δ/σ)max < 0.001
S = 1.07	Δρmax = 0.23 e Å^−3
3094 reflections	Δρmin = −0.22 e Å^−3
172 parameters	Absolute structure: Flack x determined using 1094 quotients [(I^+)-(I^-)]/[(I^+)+(I^-)] (Parsons et al., 2013)
1 restraint	Absolute structure parameter: 0.07 (4)

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.

Refinement. 1. Fixed Uiso At 1.2 times of: All C(H) groups, All C(H,H) groups 2.a Secondary CH2 refined with riding coordinates: C2(H2A,H2B) 2.b Aromatic/amide H refined with riding coordinates: C3(H3), C6(H6), C7(H7), C8(H8), C9(H9) 2.c X=CH2 refined with riding coordinates: C4(H4A,H4B)

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

	x	y	z	Uiso*/Ueq
S1	0.82933 (7)	0.43951 (3)	0.47114 (11)	0.02848 (15)
F1	0.4353 (3)	0.24877 (9)	0.1989 (3)	0.0619 (6)
F2	0.5490 (3)	0.34169 (11)	0.2020 (2)	0.0590 (6)
F3	0.2811 (3)	0.32951 (12)	0.2643 (3)	0.0614 (6)
N1	0.4878 (3)	0.41022 (10)	0.5110 (3)	0.0263 (5)
N2	0.3257 (3)	0.43591 (10)	0.4866 (5)	0.0357 (6)
N3	0.3518 (3)	0.49149 (11)	0.4245 (4)	0.0406 (7)
N4	0.5253 (3)	0.50465 (11)	0.4058 (3)	0.0348 (6)
C1	0.6066 (3)	0.45334 (10)	0.4616 (4)	0.0252 (5)
C2	0.9068 (3)	0.51253 (12)	0.3701 (3)	0.0264 (5)
H2A	1.030061	0.506647	0.335573	0.032*
H2B	0.837482	0.520356	0.265975	0.032*
C3	0.8943 (3)	0.56925 (10)	0.4825 (5)	0.0301 (5)
H3	0.781849	0.582487	0.519235	0.036*
C4	1.0299 (4)	0.60194 (13)	0.5336 (4)	0.0378 (7)
H4A	1.143885	0.589750	0.498837	0.045*
H4B	1.014415	0.637872	0.605561	0.045*
C5	0.5129 (3)	0.34687 (11)	0.5739 (3)	0.0253 (5)
C6	0.5647 (4)	0.33874 (16)	0.7405 (4)	0.0363 (7)
H6	0.580710	0.374616	0.812478	0.044*
C7	0.5933 (5)	0.27776 (17)	0.8017 (4)	0.0436 (8)
H7	0.631875	0.271828	0.915363	0.052*
C8	0.5662 (4)	0.22597 (15)	0.6992 (5)	0.0427 (8)
H8	0.583610	0.184288	0.743224	0.051*
C9	0.5136 (4)	0.23375 (13)	0.5317 (4)	0.0370 (7)
H9	0.495146	0.197514	0.461602	0.044*
C10	0.4879 (3)	0.29472 (11)	0.4665 (4)	0.0278 (5)
C11	0.4394 (4)	0.30342 (14)	0.2845 (4)	0.0373 (7)

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
S1	0.0220 (3)	0.0207 (2)	0.0428 (3)	0.0028 (2)	−0.0018 (3)	0.0025 (4)
F1	0.1032 (19)	0.0361 (10)	0.0464 (12)	−0.0050 (11)	−0.0153 (12)	−0.0163 (10)
F2	0.0844 (16)	0.0638 (14)	0.0287 (10)	−0.0314 (12)	0.0085 (10)	0.0003 (10)
F3	0.0620 (13)	0.0750 (15)	0.0472 (11)	0.0155 (11)	−0.0163 (10)	−0.0005 (11)
N1	0.0222 (10)	0.0226 (10)	0.0341 (14)	0.0019 (8)	0.0027 (9)	−0.0039 (9)
N2	0.0222 (9)	0.0327 (11)	0.0522 (16)	0.0065 (8)	0.0027 (12)	−0.0053 (13)
N3	0.0282 (12)	0.0328 (13)	0.0607 (19)	0.0074 (9)	−0.0022 (11)	−0.0004 (11)
N4	0.0269 (12)	0.0265 (11)	0.0511 (15)	0.0058 (9)	−0.0015 (11)	0.0045 (11)
C1	0.0223 (10)	0.0218 (10)	0.0317 (13)	0.0029 (8)	0.0014 (14)	−0.0030 (13)
C2	0.0260 (13)	0.0243 (13)	0.0290 (14)	−0.0003 (10)	0.0015 (11)	0.0011 (10)
C3	0.0306 (12)	0.0228 (11)	0.0368 (14)	0.0022 (9)	0.0041 (15)	0.0025 (14)
C4	0.0427 (16)	0.0251 (13)	0.0456 (18)	−0.0011 (12)	0.0008 (13)	−0.0017 (12)
C5	0.0232 (12)	0.0229 (12)	0.0297 (14)	−0.0001 (10)	0.0053 (11)	0.0001 (11)
C6	0.0404 (17)	0.0397 (17)	0.0288 (16)	0.0005 (14)	0.0036 (13)	−0.0043 (13)
C7	0.049 (2)	0.051 (2)	0.0311 (16)	0.0076 (15)	0.0049 (14)	0.0108 (14)
C8	0.0466 (18)	0.0338 (15)	0.0477 (19)	0.0052 (13)	0.0142 (15)	0.0146 (15)
C9	0.0415 (16)	0.0257 (13)	0.0440 (17)	−0.0033 (12)	0.0099 (13)	0.0025 (12)
C10	0.0279 (11)	0.0237 (11)	0.0318 (13)	−0.0034 (9)	0.0055 (14)	−0.0005 (13)
C11	0.0489 (19)	0.0294 (15)	0.0337 (16)	−0.0053 (13)	−0.0017 (13)	−0.0046 (12)

Geometric parameters (Å, º)

S1—C1	1.732 (2)	C3—C4	1.308 (4)
S1—C2	1.825 (3)	C4—H4A	0.9500
F1—C11	1.330 (3)	C4—H4B	0.9500
F2—C11	1.331 (4)	C5—C6	1.380 (4)
F3—C11	1.340 (4)	C5—C10	1.396 (4)
N1—N2	1.367 (3)	C6—H6	0.9500
N1—C1	1.341 (3)	C6—C7	1.384 (5)
N1—C5	1.431 (3)	C7—H7	0.9500
N2—N3	1.280 (3)	C7—C8	1.369 (5)
N3—N4	1.365 (3)	C8—H8	0.9500
N4—C1	1.319 (3)	C8—C9	1.387 (5)
C2—H2A	0.9900	C9—H9	0.9500
C2—H2B	0.9900	C9—C10	1.392 (4)
C2—C3	1.486 (4)	C10—C11	1.490 (4)
C3—H3	0.9500
C1—S1—C2	99.24 (12)	C6—C5—C10	121.1 (2)
N2—N1—C5	122.5 (2)	C10—C5—N1	120.0 (2)
C1—N1—N2	108.0 (2)	C5—C6—H6	120.3
C1—N1—C5	129.5 (2)	C5—C6—C7	119.3 (3)
N3—N2—N1	105.7 (2)	C7—C6—H6	120.3
N2—N3—N4	112.2 (2)	C6—C7—H7	119.8
C1—N4—N3	105.0 (2)	C8—C7—C6	120.4 (3)
N1—C1—S1	122.86 (17)	C8—C7—H7	119.8
N4—C1—S1	128.06 (19)	C7—C8—H8	119.7
N4—C1—N1	109.1 (2)	C7—C8—C9	120.6 (3)
S1—C2—H2A	109.0	C9—C8—H8	119.7
S1—C2—H2B	109.0	C8—C9—H9	120.0
H2A—C2—H2B	107.8	C8—C9—C10	120.0 (3)
C3—C2—S1	113.13 (19)	C10—C9—H9	120.0
C3—C2—H2A	109.0	C5—C10—C11	121.3 (2)
C3—C2—H2B	109.0	C9—C10—C5	118.5 (3)
C2—C3—H3	118.3	C9—C10—C11	120.1 (3)
C4—C3—C2	123.5 (2)	F1—C11—F2	106.8 (3)
C4—C3—H3	118.3	F1—C11—F3	105.7 (3)
C3—C4—H4A	120.0	F1—C11—C10	112.7 (2)
C3—C4—H4B	120.0	F2—C11—F3	105.5 (3)
H4A—C4—H4B	120.0	F2—C11—C10	112.6 (2)
C6—C5—N1	118.8 (2)	F3—C11—C10	112.9 (2)
S1—C2—C3—C4	117.0 (3)	C5—N1—N2—N3	−177.7 (2)
N1—N2—N3—N4	0.0 (4)	C5—N1—C1—S1	−1.9 (4)
N1—C5—C6—C7	−178.5 (3)	C5—N1—C1—N4	177.3 (2)
N1—C5—C10—C9	179.9 (2)	C5—C6—C7—C8	−1.6 (5)
N1—C5—C10—C11	1.5 (4)	C5—C10—C11—F1	174.8 (2)
N2—N1—C1—S1	−179.8 (3)	C5—C10—C11—F2	53.9 (4)
N2—N1—C1—N4	−0.6 (3)	C5—C10—C11—F3	−65.4 (3)
N2—N1—C5—C6	−104.5 (3)	C6—C5—C10—C9	1.1 (4)
N2—N1—C5—C10	76.6 (3)	C6—C5—C10—C11	−177.3 (3)
N2—N3—N4—C1	−0.3 (4)	C6—C7—C8—C9	1.4 (5)
N3—N4—C1—S1	179.7 (2)	C7—C8—C9—C10	0.0 (5)
N3—N4—C1—N1	0.6 (3)	C8—C9—C10—C5	−1.2 (4)
C1—S1—C2—C3	75.0 (2)	C8—C9—C10—C11	177.2 (3)
C1—N1—N2—N3	0.4 (4)	C9—C10—C11—F1	−3.6 (4)
C1—N1—C5—C6	77.8 (4)	C9—C10—C11—F2	−124.5 (3)
C1—N1—C5—C10	−101.1 (3)	C9—C10—C11—F3	116.2 (3)
C2—S1—C1—N1	175.3 (2)	C10—C5—C6—C7	0.3 (4)
C2—S1—C1—N4	−3.8 (3)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
C2—H2A···N3^i	0.99	2.58	3.464 (3)	148
C2—H2B···N2^ii	0.99	2.69	3.666 (4)	169
C3—H3···F3^iii	0.95	2.71	3.351 (3)	125
C4—H4A···N3^i	0.95	2.67	3.491 (3)	145
C4—H4B···F1^iv	0.95	2.47	3.355 (3)	155
C6—H6···N4^iii	0.95	2.76	3.601 (3)	148

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