1,3-Bis(1-phenyl-1H-tetra­zole-5-ylsulfan­yl)propane

In the title compound, C₁₇H₁₆N₈S₂, the terminal ring systems extend in opposite directions to minimize steric hindrance.

Key indicators

• Single-crystal X-ray study
• T = 293 K
• Mean [sigma](C-C) = 0.004 Å
• R factor = 0.050
• wR factor = 0.131
• Data-to-parameter ratio = 18.3

checkCIF/PLATON results

No syntax errors found



Alert level C
PLAT066_ALERT_1_C Predicted and Reported Transmissions Identical .          ?

Alert level G
PLAT199_ALERT_1_G Check the Reported _cell_measurement_temperature        293 K
PLAT200_ALERT_1_G Check the Reported _diffrn_ambient_temperature .        293 K

   0 ALERT level A = In general: serious problem
   0 ALERT level B = Potentially serious problem
   1 ALERT level C = Check and explain
   2 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
   0 ALERT type 5 Informative message, check

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Computing details

Data collection: CrystalClear (Molecular Structure Corporation & Rigaku, 1999); cell refinement: CrystalClear; data reduction: CrystalStructure (Rigaku/MSC, 2005); 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.

1,3-Bis(1-phenyl-1H-tetrazole-5-ylsulfanyl)propane

Crystal data

C17H16N8S2	F(000) = 824
Mr = 396.5	Dx = 1.396 Mg m^−3
Monoclinic, P21/n	Melting point: 372 K
Hall symbol: -P 2yn	Mo Kα radiation, λ = 0.71073 Å
a = 16.774 (3) Å	Cell parameters from 5232 reflections
b = 6.5029 (13) Å	θ = 2.3–27.2°
c = 18.691 (4) Å	µ = 0.30 mm^−1
β = 112.24 (3)°	T = 293 K
V = 1887.1 (8) Å^3	Plate, colourless
Z = 4	0.14 × 0.12 × 0.10 mm

Data collection

Rigaku Saturn 70 diffractometer	4478 independent reflections
Radiation source: rotating anode	3342 reflections with I > 2σ(I)
Confocal monochromator	Rint = 0.048
Detector resolution: 7.31 pixels mm^-1	θmax = 27.9°, θmin = 1.4°
ω scans	h = −22→19
Absorption correction: multi-scan (REQAB; Jacobson, 1998)	k = −7→8
Tmin = 0.959, Tmax = 0.970	l = −24→24
14105 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)] = 0.050	H-atom parameters constrained
wR(F^2) = 0.131	w = 1/[σ^2(Fo^2) + (0.0652P)^2] where P = (Fo^2 + 2Fc^2)/3
S = 1.10	(Δ/σ)max = 0.002
4478 reflections	Δρmax = 0.24 e Å^−3
245 parameters	Δρmin = −0.30 e Å^−3
0 restraints	Extinction correction: SHELXL97
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.0165 (19)

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	0.17882 (3)	1.23458 (8)	1.03342 (3)	0.04799 (17)
S2	0.11140 (4)	0.83195 (9)	0.79835 (3)	0.05260 (19)
N1	0.04608 (10)	1.2317 (2)	1.08302 (8)	0.0389 (4)
N2	−0.04119 (10)	1.2434 (2)	1.05572 (10)	0.0455 (4)
N3	−0.06596 (11)	1.2642 (2)	0.98180 (10)	0.0474 (4)
N4	0.00229 (11)	1.2653 (2)	0.95911 (9)	0.0444 (4)
N5	0.19750 (11)	1.0604 (3)	0.72532 (10)	0.0539 (4)
N6	0.19470 (14)	1.0695 (3)	0.65123 (11)	0.0685 (5)
N7	0.14153 (13)	0.9381 (3)	0.60708 (10)	0.0650 (5)
N8	0.10687 (10)	0.8364 (3)	0.65240 (9)	0.0466 (4)
C1	0.09563 (12)	1.2158 (3)	1.16485 (10)	0.0429 (4)
C2	0.13872 (15)	1.0367 (4)	1.19400 (12)	0.0605 (6)
H2	0.1368	0.9267	1.1616	0.073*
C3	0.18515 (17)	1.0233 (5)	1.27279 (14)	0.0779 (8)
H3	0.2148	0.9031	1.2938	0.094*
C4	0.18764 (19)	1.1863 (5)	1.31981 (15)	0.0822 (8)
H4	0.2193	1.1767	1.3727	0.099*
C5	0.14372 (19)	1.3639 (5)	1.28955 (14)	0.0798 (8)
H5	0.1453	1.4735	1.3221	0.096*
C6	0.09696 (15)	1.3810 (4)	1.21086 (13)	0.0610 (6)
H6	0.0673	1.5012	1.1898	0.073*
C7	0.07152 (12)	1.2454 (2)	1.02300 (10)	0.0373 (4)
C8	0.17388 (15)	1.3429 (3)	0.94242 (11)	0.0518 (5)
H8A	0.1431	1.4726	0.9346	0.062*
H8B	0.2322	1.3731	0.9468	0.062*
C9	0.13129 (15)	1.2107 (3)	0.87103 (11)	0.0520 (5)
H9A	0.0716	1.1881	0.8641	0.062*
H9B	0.1317	1.2851	0.8262	0.062*
C10	0.17444 (12)	1.0044 (3)	0.87479 (10)	0.0455 (5)
H10A	0.1841	0.9409	0.9243	0.055*
H10B	0.2301	1.0257	0.8714	0.055*
C11	0.14204 (12)	0.9143 (3)	0.72444 (10)	0.0436 (4)
C12	0.04254 (12)	0.6805 (3)	0.62220 (10)	0.0466 (5)
C13	0.05662 (14)	0.4895 (3)	0.65652 (13)	0.0593 (6)
H13	0.1075	0.4617	0.6982	0.071*
C14	−0.00601 (18)	0.3396 (4)	0.62813 (16)	0.0744 (7)
H14	0.0016	0.2109	0.6515	0.089*
C15	−0.07975 (18)	0.3827 (5)	0.56493 (17)	0.0827 (9)
H15	−0.1216	0.2816	0.5454	0.099*
C16	−0.09226 (16)	0.5724 (6)	0.53049 (15)	0.0811 (8)
H16	−0.1421	0.5985	0.4875	0.097*
C17	−0.03113 (15)	0.7251 (4)	0.55937 (13)	0.0645 (6)
H17	−0.0396	0.8550	0.5369	0.077*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
S1	0.0411 (3)	0.0684 (4)	0.0354 (3)	−0.0024 (2)	0.0156 (2)	−0.0061 (2)
S2	0.0591 (4)	0.0636 (4)	0.0384 (3)	−0.0133 (2)	0.0222 (2)	−0.0082 (2)
N1	0.0396 (9)	0.0407 (8)	0.0370 (8)	0.0004 (6)	0.0153 (7)	−0.0008 (6)
N2	0.0396 (9)	0.0466 (9)	0.0504 (10)	0.0012 (7)	0.0173 (7)	0.0000 (7)
N3	0.0422 (9)	0.0449 (9)	0.0503 (10)	0.0000 (7)	0.0123 (8)	−0.0010 (7)
N4	0.0465 (10)	0.0448 (9)	0.0385 (9)	−0.0024 (7)	0.0122 (7)	−0.0024 (6)
N5	0.0522 (11)	0.0627 (11)	0.0522 (10)	−0.0093 (8)	0.0259 (8)	−0.0071 (8)
N6	0.0732 (13)	0.0869 (14)	0.0580 (12)	−0.0157 (11)	0.0389 (10)	−0.0055 (10)
N7	0.0675 (13)	0.0896 (14)	0.0468 (11)	−0.0114 (11)	0.0319 (10)	−0.0036 (10)
N8	0.0446 (10)	0.0623 (10)	0.0370 (9)	−0.0003 (7)	0.0202 (7)	−0.0042 (7)
C1	0.0417 (11)	0.0551 (11)	0.0344 (10)	−0.0019 (8)	0.0173 (8)	−0.0008 (8)
C2	0.0693 (15)	0.0615 (13)	0.0458 (12)	0.0092 (11)	0.0160 (11)	0.0046 (10)
C3	0.0815 (18)	0.0920 (19)	0.0503 (14)	0.0168 (15)	0.0138 (13)	0.0163 (13)
C4	0.0763 (19)	0.128 (3)	0.0380 (13)	0.0050 (17)	0.0171 (12)	0.0058 (14)
C5	0.0817 (19)	0.111 (2)	0.0494 (15)	0.0000 (16)	0.0274 (13)	−0.0249 (14)
C6	0.0652 (15)	0.0706 (15)	0.0495 (13)	0.0049 (11)	0.0242 (11)	−0.0105 (10)
C7	0.0422 (10)	0.0364 (9)	0.0330 (9)	−0.0040 (7)	0.0140 (8)	−0.0051 (7)
C8	0.0668 (14)	0.0487 (11)	0.0515 (13)	−0.0013 (10)	0.0353 (11)	−0.0013 (9)
C9	0.0607 (13)	0.0640 (13)	0.0339 (10)	0.0118 (10)	0.0207 (9)	0.0046 (9)
C10	0.0441 (11)	0.0579 (12)	0.0329 (10)	0.0026 (9)	0.0128 (8)	−0.0020 (8)
C11	0.0412 (10)	0.0532 (11)	0.0371 (10)	0.0020 (8)	0.0156 (8)	−0.0058 (8)
C12	0.0424 (11)	0.0652 (13)	0.0326 (10)	−0.0010 (9)	0.0147 (8)	−0.0125 (8)
C13	0.0555 (13)	0.0615 (14)	0.0564 (13)	0.0007 (10)	0.0163 (11)	−0.0162 (10)
C14	0.0774 (18)	0.0653 (15)	0.0851 (19)	−0.0118 (13)	0.0359 (15)	−0.0287 (13)
C15	0.0672 (18)	0.107 (2)	0.081 (2)	−0.0290 (16)	0.0364 (15)	−0.0534 (17)
C16	0.0493 (14)	0.135 (3)	0.0500 (15)	−0.0052 (15)	0.0090 (11)	−0.0306 (16)
C17	0.0538 (14)	0.0968 (18)	0.0412 (12)	0.0036 (12)	0.0161 (10)	−0.0058 (11)

Geometric parameters (Å, º)

S1—C7	1.737 (2)	C4—H4	0.9300
S1—C8	1.814 (2)	C5—C6	1.385 (3)
S2—C11	1.731 (2)	C5—H5	0.9300
S2—C10	1.8094 (19)	C6—H6	0.9300
N1—C7	1.346 (2)	C8—C9	1.519 (3)
N1—N2	1.358 (2)	C8—H8A	0.9700
N1—C1	1.442 (2)	C8—H8B	0.9700
N2—N3	1.291 (2)	C9—C10	1.513 (3)
N3—N4	1.363 (2)	C9—H9A	0.9700
N4—C7	1.320 (2)	C9—H9B	0.9700
N5—C11	1.325 (3)	C10—H10A	0.9700
N5—N6	1.369 (2)	C10—H10B	0.9700
N6—N7	1.284 (3)	C12—C17	1.376 (3)
N7—N8	1.366 (2)	C12—C13	1.376 (3)
N8—C11	1.348 (2)	C13—C14	1.383 (3)
N8—C12	1.432 (3)	C13—H13	0.9300
C1—C2	1.370 (3)	C14—C15	1.378 (4)
C1—C6	1.371 (3)	C14—H14	0.9300
C2—C3	1.384 (3)	C15—C16	1.371 (4)
C2—H2	0.9300	C15—H15	0.9300
C3—C4	1.367 (4)	C16—C17	1.382 (4)
C3—H3	0.9300	C16—H16	0.9300
C4—C5	1.372 (4)	C17—H17	0.9300
C7—S1—C8	101.63 (10)	S1—C8—H8A	108.2
C11—S2—C10	100.19 (10)	C9—C8—H8B	108.2
C7—N1—N2	108.66 (15)	S1—C8—H8B	108.2
C7—N1—C1	130.67 (16)	H8A—C8—H8B	107.4
N2—N1—C1	120.63 (16)	C10—C9—C8	113.78 (16)
N3—N2—N1	105.83 (16)	C10—C9—H9A	108.8
N2—N3—N4	111.45 (15)	C8—C9—H9A	108.8
C7—N4—N3	105.84 (16)	C10—C9—H9B	108.8
C11—N5—N6	105.28 (17)	C8—C9—H9B	108.8
N7—N6—N5	111.75 (18)	H9A—C9—H9B	107.7
N6—N7—N8	106.19 (17)	C9—C10—S2	112.74 (13)
C11—N8—N7	108.02 (17)	C9—C10—H10A	109.0
C11—N8—C12	129.77 (17)	S2—C10—H10A	109.0
N7—N8—C12	122.19 (16)	C9—C10—H10B	109.0
C2—C1—C6	122.4 (2)	S2—C10—H10B	109.0
C2—C1—N1	119.21 (17)	H10A—C10—H10B	107.8
C6—C1—N1	118.38 (18)	N5—C11—N8	108.76 (18)
C1—C2—C3	118.4 (2)	N5—C11—S2	129.12 (15)
C1—C2—H2	120.8	N8—C11—S2	122.07 (15)
C3—C2—H2	120.8	C17—C12—C13	121.9 (2)
C4—C3—C2	120.2 (2)	C17—C12—N8	119.1 (2)
C4—C3—H3	119.9	C13—C12—N8	118.97 (18)
C2—C3—H3	119.9	C12—C13—C14	119.1 (2)
C3—C4—C5	120.4 (2)	C12—C13—H13	120.5
C3—C4—H4	119.8	C14—C13—H13	120.5
C5—C4—H4	119.8	C15—C14—C13	119.4 (3)
C4—C5—C6	120.4 (2)	C15—C14—H14	120.3
C4—C5—H5	119.8	C13—C14—H14	120.3
C6—C5—H5	119.8	C16—C15—C14	120.9 (2)
C1—C6—C5	118.1 (2)	C16—C15—H15	119.5
C1—C6—H6	120.9	C14—C15—H15	119.5
C5—C6—H6	120.9	C15—C16—C17	120.3 (2)
N4—C7—N1	108.23 (17)	C15—C16—H16	119.9
N4—C7—S1	128.68 (15)	C17—C16—H16	119.9
N1—C7—S1	123.09 (14)	C12—C17—C16	118.4 (3)
C9—C8—S1	116.31 (14)	C12—C17—H17	120.8
C9—C8—H8A	108.2	C16—C17—H17	120.8
C7—N1—N2—N3	−0.27 (19)	C8—S1—C7—N4	18.53 (18)
C1—N1—N2—N3	177.51 (15)	C8—S1—C7—N1	−162.13 (15)
N1—N2—N3—N4	0.42 (19)	C7—S1—C8—C9	−70.86 (18)
N2—N3—N4—C7	−0.4 (2)	S1—C8—C9—C10	−59.4 (2)
C11—N5—N6—N7	−0.2 (3)	C8—C9—C10—S2	168.98 (15)
N5—N6—N7—N8	0.1 (3)	C11—S2—C10—C9	83.77 (17)
N6—N7—N8—C11	0.1 (2)	N6—N5—C11—N8	0.3 (2)
N6—N7—N8—C12	178.30 (18)	N6—N5—C11—S2	−177.18 (16)
C7—N1—C1—C2	−70.9 (3)	N7—N8—C11—N5	−0.2 (2)
N2—N1—C1—C2	111.9 (2)	C12—N8—C11—N5	−178.27 (19)
C7—N1—C1—C6	109.8 (2)	N7—N8—C11—S2	177.45 (15)
N2—N1—C1—C6	−67.4 (2)	C12—N8—C11—S2	−0.6 (3)
C6—C1—C2—C3	0.0 (4)	C10—S2—C11—N5	1.2 (2)
N1—C1—C2—C3	−179.3 (2)	C10—S2—C11—N8	−175.99 (16)
C1—C2—C3—C4	−0.2 (4)	C11—N8—C12—C17	123.9 (2)
C2—C3—C4—C5	0.5 (5)	N7—N8—C12—C17	−53.9 (3)
C3—C4—C5—C6	−0.6 (5)	C11—N8—C12—C13	−56.7 (3)
C2—C1—C6—C5	−0.1 (4)	N7—N8—C12—C13	125.5 (2)
N1—C1—C6—C5	179.1 (2)	C17—C12—C13—C14	−1.5 (3)
C4—C5—C6—C1	0.4 (4)	N8—C12—C13—C14	179.1 (2)
N3—N4—C7—N1	0.23 (19)	C12—C13—C14—C15	1.9 (4)
N3—N4—C7—S1	179.65 (13)	C13—C14—C15—C16	−0.8 (4)
N2—N1—C7—N4	0.01 (19)	C14—C15—C16—C17	−0.8 (4)
C1—N1—C7—N4	−177.46 (16)	C13—C12—C17—C16	0.0 (3)
N2—N1—C7—S1	−179.44 (12)	N8—C12—C17—C16	179.4 (2)
C1—N1—C7—S1	3.1 (3)	C15—C16—C17—C12	1.1 (4)