1,4-Bis(1-phenyl-1H-tetrazol-5-ylsulfanyl)butane

In the title compound, C₁₈H₁₈N₈S₂, the two 1-phenyl-1H-tetrazole-5-thiol moieties are located on the same side of the butane-1,4-diyl chain but point in opposite directions.

Key indicators

• Single-crystal X-ray study
• T = 293 K
• Mean [sigma](C-C) = 0.004 Å
• R factor = 0.038
• wR factor = 0.109
• Data-to-parameter ratio = 15.6

checkCIF/PLATON results

No syntax errors found



Alert level C
PLAT066_ALERT_1_C Predicted and Reported Transmissions Identical .          ?
PLAT199_ALERT_1_C Check the Reported cell_measurement_temperature         293
PLAT200_ALERT_1_C Check the Reported cell_ambient_temperature ....        293

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

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

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Computing details

Data collection: SMART (Bruker, 1997); cell refinement: SMART; data reduction: SAINT (Bruker, 1997); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: SHELXTL (Bruker, 1997); software used to prepare material for publication: SHELXTL.

1,4-Bis(1-phenyl-1H-tetrazol-5-ylsulfanyl)butane

Crystal data

C18H18N8S2	F(000) = 856
Mr = 410.52	Dx = 1.414 Mg m^−3
Monoclinic, P21/c	Melting point = 415–416 K
Hall symbol: -P 2ybc	Mo Kα radiation, λ = 0.71073 Å
a = 9.4630 (17) Å	Cell parameters from 2155 reflections
b = 12.879 (2) Å	θ = 2.6–26.2°
c = 16.440 (3) Å	µ = 0.30 mm^−1
β = 105.802 (3)°	T = 293 K
V = 1927.9 (6) Å^3	Prism, colorless
Z = 4	0.42 × 0.38 × 0.22 mm

Data collection

Bruker SMART CCD area-detector diffractometer	3955 independent reflections
Radiation source: fine-focus sealed tube	2953 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.023
φ and ω scans	θmax = 26.4°, θmin = 2.0°
Absorption correction: multi-scan (SADABS; Sheldrick, 1997)	h = −11→11
Tmin = 0.882, Tmax = 0.936	k = −16→14
10993 measured reflections	l = −20→14

Refinement

Refinement on F^2	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F^2 > 2σ(F^2)] = 0.038	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.109	H-atom parameters constrained
S = 1.02	w = 1/[σ^2(Fo^2) + (0.0551P)^2 + 0.5664P] where P = (Fo^2 + 2Fc^2)/3
3955 reflections	(Δ/σ)max = 0.001
253 parameters	Δρmax = 0.35 e Å^−3
0 restraints	Δρmin = −0.32 e Å^−3

Special details

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
S1	0.41059 (5)	1.01832 (4)	0.16222 (3)	0.04481 (15)
S2	0.09992 (5)	0.88290 (4)	−0.13239 (4)	0.04896 (16)
N1	0.32915 (16)	0.81828 (12)	0.17635 (10)	0.0398 (4)
N2	0.20960 (19)	0.76171 (14)	0.17988 (12)	0.0541 (5)
N3	0.1052 (2)	0.82723 (16)	0.17606 (13)	0.0587 (5)
N4	0.15159 (18)	0.92654 (14)	0.17043 (12)	0.0515 (4)
N5	0.37173 (18)	0.79459 (15)	−0.11627 (12)	0.0523 (5)
N6	0.4265 (2)	0.69609 (17)	−0.10528 (13)	0.0616 (5)
N7	0.3285 (2)	0.63031 (15)	−0.09803 (13)	0.0581 (5)
N8	0.20334 (17)	0.68626 (13)	−0.10386 (10)	0.0427 (4)
C1	0.5942 (2)	0.80484 (16)	0.22856 (13)	0.0456 (5)
H1	0.5937	0.8567	0.2678	0.055*
C2	0.7247 (2)	0.76109 (18)	0.22364 (15)	0.0550 (6)
H2	0.8131	0.7848	0.2589	0.066*
C3	0.7249 (3)	0.6832 (2)	0.16747 (17)	0.0665 (7)
H3	0.8133	0.6541	0.1646	0.080*
C4	0.5946 (3)	0.6476 (2)	0.11488 (18)	0.0739 (8)
H4	0.5953	0.5933	0.0777	0.089*
C5	0.4628 (3)	0.69213 (17)	0.11721 (15)	0.0579 (6)
H5	0.3747	0.6696	0.0809	0.069*
C6	0.4647 (2)	0.77044 (14)	0.17439 (12)	0.0400 (4)
C7	0.2910 (2)	0.91939 (15)	0.17055 (12)	0.0396 (4)
C8	0.2820 (2)	1.10894 (15)	0.09688 (13)	0.0431 (5)
H8A	0.2103	1.1285	0.1266	0.052*
H8B	0.3350	1.1712	0.0898	0.052*
C9	0.2002 (2)	1.06842 (16)	0.00957 (13)	0.0461 (5)
H9A	0.1396	1.0102	0.0165	0.055*
H9B	0.1352	1.1226	−0.0202	0.055*
C10	0.2978 (2)	1.03395 (16)	−0.04467 (13)	0.0451 (5)
H10A	0.3599	1.0915	−0.0512	0.054*
H10B	0.3611	0.9783	−0.0160	0.054*
C11	0.2116 (2)	0.99668 (15)	−0.13130 (13)	0.0431 (5)
H11A	0.2803	0.9820	−0.1642	0.052*
H11B	0.1484	1.0527	−0.1593	0.052*
C12	0.2330 (2)	0.78628 (15)	−0.11573 (12)	0.0421 (4)
C13	0.0704 (2)	0.63758 (15)	−0.09756 (12)	0.0425 (5)
C14	0.0193 (3)	0.55094 (16)	−0.14594 (14)	0.0545 (6)
H14	0.0699	0.5241	−0.1824	0.065*
C15	−0.1089 (3)	0.50498 (19)	−0.13890 (17)	0.0698 (7)
H15	−0.1445	0.4459	−0.1703	0.084*
C16	−0.1843 (3)	0.5461 (2)	−0.08572 (19)	0.0718 (8)
H16	−0.2710	0.5150	−0.0819	0.086*
C17	−0.1330 (3)	0.6319 (2)	−0.03857 (17)	0.0669 (7)
H17	−0.1854	0.6597	−0.0034	0.080*
C18	−0.0029 (2)	0.67791 (17)	−0.04296 (14)	0.0518 (5)
H18	0.0343	0.7352	−0.0095	0.062*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
S1	0.0300 (3)	0.0443 (3)	0.0588 (3)	−0.00080 (19)	0.0099 (2)	0.0001 (2)
S2	0.0299 (3)	0.0424 (3)	0.0746 (4)	0.0000 (2)	0.0144 (2)	−0.0017 (2)
N1	0.0337 (8)	0.0433 (9)	0.0420 (9)	−0.0039 (7)	0.0099 (7)	0.0000 (7)
N2	0.0438 (10)	0.0546 (11)	0.0635 (12)	−0.0116 (8)	0.0139 (8)	0.0055 (9)
N3	0.0394 (10)	0.0677 (12)	0.0707 (13)	−0.0054 (9)	0.0181 (9)	0.0092 (10)
N4	0.0360 (9)	0.0569 (11)	0.0659 (12)	0.0011 (8)	0.0211 (8)	0.0033 (9)
N5	0.0350 (9)	0.0611 (11)	0.0625 (12)	0.0050 (8)	0.0159 (8)	−0.0039 (9)
N6	0.0447 (11)	0.0709 (13)	0.0714 (14)	0.0142 (10)	0.0195 (9)	−0.0048 (10)
N7	0.0519 (11)	0.0576 (11)	0.0639 (12)	0.0209 (9)	0.0145 (9)	−0.0035 (9)
N8	0.0384 (9)	0.0437 (9)	0.0459 (9)	0.0080 (7)	0.0110 (7)	−0.0034 (7)
C1	0.0422 (11)	0.0454 (11)	0.0473 (11)	0.0030 (9)	0.0089 (9)	0.0035 (9)
C2	0.0426 (12)	0.0578 (13)	0.0625 (14)	0.0099 (10)	0.0107 (10)	0.0153 (11)
C3	0.0596 (15)	0.0666 (16)	0.0783 (18)	0.0258 (12)	0.0272 (13)	0.0159 (14)
C4	0.093 (2)	0.0581 (15)	0.0755 (18)	0.0200 (14)	0.0316 (16)	−0.0101 (13)
C5	0.0630 (14)	0.0515 (13)	0.0571 (14)	0.0031 (11)	0.0126 (11)	−0.0086 (11)
C6	0.0413 (10)	0.0384 (10)	0.0409 (11)	0.0040 (8)	0.0125 (8)	0.0053 (8)
C7	0.0339 (10)	0.0465 (11)	0.0394 (10)	0.0001 (8)	0.0118 (8)	−0.0013 (8)
C8	0.0353 (10)	0.0369 (10)	0.0586 (13)	0.0039 (8)	0.0152 (9)	−0.0058 (9)
C9	0.0341 (10)	0.0457 (11)	0.0584 (13)	0.0042 (8)	0.0123 (9)	−0.0013 (9)
C10	0.0314 (10)	0.0484 (11)	0.0573 (13)	−0.0042 (8)	0.0151 (9)	−0.0018 (9)
C11	0.0342 (10)	0.0457 (11)	0.0510 (12)	−0.0008 (8)	0.0140 (9)	0.0031 (9)
C12	0.0371 (10)	0.0472 (11)	0.0416 (11)	0.0022 (8)	0.0100 (8)	−0.0067 (9)
C13	0.0478 (11)	0.0372 (10)	0.0401 (11)	0.0064 (8)	0.0080 (9)	0.0075 (8)
C14	0.0732 (15)	0.0400 (11)	0.0480 (13)	0.0010 (10)	0.0126 (11)	0.0050 (9)
C15	0.0873 (19)	0.0462 (13)	0.0669 (16)	−0.0185 (13)	0.0056 (14)	0.0115 (12)
C16	0.0687 (17)	0.0624 (16)	0.0839 (19)	−0.0126 (13)	0.0202 (14)	0.0292 (14)
C17	0.0725 (16)	0.0632 (15)	0.0755 (17)	0.0081 (13)	0.0381 (14)	0.0211 (13)
C18	0.0576 (13)	0.0482 (12)	0.0531 (13)	0.0033 (10)	0.0209 (10)	0.0043 (10)

Geometric parameters (Å, º)

S1—C7	1.7340 (19)	C5—C6	1.376 (3)
S1—C8	1.813 (2)	C5—H5	0.9300
S2—C12	1.738 (2)	C8—C9	1.525 (3)
S2—C11	1.8042 (19)	C8—H8A	0.9700
N1—C7	1.348 (2)	C8—H8B	0.9700
N1—N2	1.360 (2)	C9—C10	1.514 (3)
N1—C6	1.431 (2)	C9—H9A	0.9700
N2—N3	1.288 (3)	C9—H9B	0.9700
N3—N4	1.364 (3)	C10—C11	1.514 (3)
N4—C7	1.322 (2)	C10—H10A	0.9700
N5—C12	1.319 (2)	C10—H10B	0.9700
N5—N6	1.363 (3)	C11—H11A	0.9700
N6—N7	1.285 (3)	C11—H11B	0.9700
N7—N8	1.367 (2)	C13—C18	1.377 (3)
N8—C12	1.344 (3)	C13—C14	1.379 (3)
N8—C13	1.434 (3)	C14—C15	1.383 (3)
C1—C6	1.378 (3)	C14—H14	0.9300
C1—C2	1.380 (3)	C15—C16	1.376 (4)
C1—H1	0.9300	C15—H15	0.9300
C2—C3	1.363 (4)	C16—C17	1.361 (4)
C2—H2	0.9300	C16—H16	0.9300
C3—C4	1.378 (4)	C17—C18	1.386 (3)
C3—H3	0.9300	C17—H17	0.9300
C4—C5	1.383 (3)	C18—H18	0.9300
C4—H4	0.9300
C7—S1—C8	99.94 (9)	H8A—C8—H8B	107.5
C12—S2—C11	100.51 (9)	C10—C9—C8	114.85 (16)
C7—N1—N2	108.12 (16)	C10—C9—H9A	108.6
C7—N1—C6	129.70 (16)	C8—C9—H9A	108.6
N2—N1—C6	122.09 (16)	C10—C9—H9B	108.6
N3—N2—N1	106.44 (17)	C8—C9—H9B	108.6
N2—N3—N4	111.15 (16)	H9A—C9—H9B	107.5
C7—N4—N3	105.92 (17)	C11—C10—C9	112.88 (16)
C12—N5—N6	105.45 (18)	C11—C10—H10A	109.0
N7—N6—N5	111.58 (17)	C9—C10—H10A	109.0
N6—N7—N8	106.20 (17)	C11—C10—H10B	109.0
C12—N8—N7	107.71 (17)	C9—C10—H10B	109.0
C12—N8—C13	130.65 (16)	H10A—C10—H10B	107.8
N7—N8—C13	121.63 (17)	C10—C11—S2	115.52 (14)
C6—C1—C2	118.9 (2)	C10—C11—H11A	108.4
C6—C1—H1	120.5	S2—C11—H11A	108.4
C2—C1—H1	120.5	C10—C11—H11B	108.4
C3—C2—C1	120.4 (2)	S2—C11—H11B	108.4
C3—C2—H2	119.8	H11A—C11—H11B	107.5
C1—C2—H2	119.8	N5—C12—N8	109.04 (17)
C2—C3—C4	120.3 (2)	N5—C12—S2	128.34 (17)
C2—C3—H3	119.8	N8—C12—S2	122.54 (15)
C4—C3—H3	119.8	C18—C13—C14	121.4 (2)
C3—C4—C5	120.2 (2)	C18—C13—N8	119.33 (18)
C3—C4—H4	119.9	C14—C13—N8	119.25 (19)
C5—C4—H4	119.9	C13—C14—C15	118.4 (2)
C6—C5—C4	118.7 (2)	C13—C14—H14	120.8
C6—C5—H5	120.7	C15—C14—H14	120.8
C4—C5—H5	120.7	C16—C15—C14	120.5 (2)
C5—C6—C1	121.40 (19)	C16—C15—H15	119.8
C5—C6—N1	119.10 (18)	C14—C15—H15	119.8
C1—C6—N1	119.49 (17)	C17—C16—C15	120.6 (2)
N4—C7—N1	108.37 (17)	C17—C16—H16	119.7
N4—C7—S1	128.39 (16)	C15—C16—H16	119.7
N1—C7—S1	123.22 (14)	C16—C17—C18	120.1 (2)
C9—C8—S1	115.09 (13)	C16—C17—H17	120.0
C9—C8—H8A	108.5	C18—C17—H17	120.0
S1—C8—H8A	108.5	C13—C18—C17	119.0 (2)
C9—C8—H8B	108.5	C13—C18—H18	120.5
S1—C8—H8B	108.5	C17—C18—H18	120.5
C7—N1—N2—N3	0.2 (2)	C8—S1—C7—N1	147.26 (16)
C6—N1—N2—N3	−176.51 (17)	C7—S1—C8—C9	−61.55 (16)
N1—N2—N3—N4	−0.3 (2)	S1—C8—C9—C10	−57.9 (2)
N2—N3—N4—C7	0.3 (2)	C8—C9—C10—C11	−178.72 (17)
C12—N5—N6—N7	−0.2 (2)	C9—C10—C11—S2	−63.3 (2)
N5—N6—N7—N8	−0.3 (2)	C12—S2—C11—C10	−78.22 (16)
N6—N7—N8—C12	0.7 (2)	N6—N5—C12—N8	0.7 (2)
N6—N7—N8—C13	−179.39 (18)	N6—N5—C12—S2	−176.26 (16)
C6—C1—C2—C3	−1.6 (3)	N7—N8—C12—N5	−0.9 (2)
C1—C2—C3—C4	0.1 (4)	C13—N8—C12—N5	179.25 (18)
C2—C3—C4—C5	1.6 (4)	N7—N8—C12—S2	176.26 (14)
C3—C4—C5—C6	−1.7 (4)	C13—N8—C12—S2	−3.6 (3)
C4—C5—C6—C1	0.1 (3)	C11—S2—C12—N5	−9.6 (2)
C4—C5—C6—N1	179.0 (2)	C11—S2—C12—N8	173.81 (17)
C2—C1—C6—C5	1.5 (3)	C12—N8—C13—C18	−50.2 (3)
C2—C1—C6—N1	−177.30 (18)	N7—N8—C13—C18	130.0 (2)
C7—N1—C6—C5	−126.1 (2)	C12—N8—C13—C14	130.3 (2)
N2—N1—C6—C5	49.8 (3)	N7—N8—C13—C14	−49.6 (3)
C7—N1—C6—C1	52.7 (3)	C18—C13—C14—C15	0.3 (3)
N2—N1—C6—C1	−131.4 (2)	N8—C13—C14—C15	179.90 (19)
N3—N4—C7—N1	−0.2 (2)	C13—C14—C15—C16	1.0 (3)
N3—N4—C7—S1	178.29 (15)	C14—C15—C16—C17	−0.7 (4)
N2—N1—C7—N4	0.0 (2)	C15—C16—C17—C18	−0.9 (4)
C6—N1—C7—N4	176.35 (18)	C14—C13—C18—C17	−1.9 (3)
N2—N1—C7—S1	−178.55 (14)	N8—C13—C18—C17	178.57 (19)
C6—N1—C7—S1	−2.2 (3)	C16—C17—C18—C13	2.1 (3)
C8—S1—C7—N4	−31.0 (2)