N,N′-Bis(tert-butoxy­carbonyl)­thio­urea

The title compound, C₁₁H₂₀O₄N₂S, has a planar skeleton and its crystal structure is stabilized by extensive intermolecular (N—H...S) and intramolecular (N—H...O and C—H...O) hydrogen-bonding interactions.

Key indicators

• Single-crystal X-ray study
• T = 298 K
• Mean [sigma](C-C) = 0.004 Å
• R factor = 0.045
• wR factor = 0.057
• Data-to-parameter ratio = 13.4

checkCIF results

No syntax errors found

ADDSYM reports no extra symmetry

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Computing details

Data collection: SMART (Bruker, 1996); cell refinement: SMART; data reduction: SAINT-Plus (Bruker, 1999); program(s) used to solve structure: SIR92 (Altomare et al., 1994); program(s) used to refine structure: TEXSAN (Molecular Structure corporation, 1992); software used to prepare material for publication: TEXSAN.

(I)

Crystal data

C11H20N2O4S	Z = 2
Mr = 276.35	F(000) = 296
Triclinic, P1	Dx = 1.184 Mg m^−3
Hall symbol: -P 1	Mo Kα radiation, λ = 0.7107 Å
a = 6.171 (2) Å	Cell parameters from 31 reflections
b = 11.334 (3) Å	θ = >0.0–28.0°
c = 11.653 (3) Å	µ = 0.22 mm^−1
α = 81.25 (1)°	T = 298 K
β = 87.31 (1)°	Block, colourless
γ = 74.27 (1)°	0.39 × 0.15 × 0.08 mm
V = 775.4 (4) Å^3

Data collection

Bruker SMART 1K CCD area-detector diffractometer	3344 independent reflections
Radiation source: X-ray tube	2188 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.020
φ and ω scans	θmax = 27°, θmin = 2.5°
Absorption correction: multi-scan SADABS (Bruker, 1997)	h = 0→7
Tmin = 0.960, Tmax = 0.984	k = −13→14
4811 measured reflections	l = −14→14

Refinement

Refinement on F	0 restraints
Least-squares matrix: full	H-atom parameters constrained
R[F^2 > 2σ(F^2)] = 0.045	Weighting scheme based on measured s.u.'s w = 1/[σ^2(Fo) + 0.0005(Fo)^2]
wR(F^2) = 0.057	(Δ/σ)max < 0.001
S = 1.57	Δρmax = 0.27 e Å^−3
2188 reflections	Δρmin = −0.16 e Å^−3
163 parameters

Special details

Refinement. Hydrogen atoms were included in the riding model approximation.

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

	x	y	z	Uiso*/Ueq
S1	0.3416 (1)	0.46403 (6)	0.35133 (5)	0.0723 (2)
O1	−0.0711 (3)	0.1878 (1)	0.3847 (1)	0.0595 (5)
O2	0.1220 (3)	0.2897 (2)	0.2535 (2)	0.0842 (7)
O3	0.3157 (3)	0.3592 (1)	0.7606 (1)	0.0636 (5)
O4	0.1290 (3)	0.2465 (2)	0.6795 (1)	0.0704 (6)
N1	0.1145 (3)	0.3021 (2)	0.4496 (2)	0.0597 (6)
N2	0.2920 (3)	0.3867 (2)	0.5710 (2)	0.0595 (6)
C1	−0.2676 (5)	0.1982 (3)	0.2029 (2)	0.0809 (10)
C2	0.0682 (5)	0.0223 (3)	0.2682 (3)	0.093 (1)
C3	−0.2916 (5)	0.0517 (2)	0.3803 (2)	0.0755 (9)
C4	−0.1385 (4)	0.1142 (2)	0.3043 (2)	0.0587 (7)
C5	0.0600 (4)	0.2630 (2)	0.3487 (2)	0.0579 (7)
C6	0.2455 (4)	0.3799 (2)	0.4579 (2)	0.0535 (7)
C7	0.3783 (5)	0.3898 (3)	0.9475 (2)	0.0813 (10)
C8	0.3980 (6)	0.1766 (3)	0.9081 (3)	0.110 (1)
C9	0.0285 (5)	0.3381 (3)	0.9062 (2)	0.091 (1)
C10	0.2761 (4)	0.3121 (2)	0.8828 (2)	0.0586 (7)
C11	0.2348 (4)	0.3222 (2)	0.6732 (2)	0.0555 (7)
H1N	0.0581	0.2735	0.5143	0.0717
H1A	−0.1761	0.2461	0.1620	0.0971
H1B	−0.3086	0.1497	0.1523	0.0971
H1C	−0.3996	0.2518	0.2304	0.0971
H2N	0.3682	0.4391	0.5793	0.0714
H2A	0.1381	−0.0309	0.3350	0.1121
H2B	0.0272	−0.0254	0.2168	0.1121
H2C	0.1702	0.0651	0.2301	0.1121
H3A	−0.4146	0.1128	0.4061	0.0906
H3B	−0.3465	0.0012	0.3372	0.0906
H3C	−0.2101	0.0017	0.4455	0.0906
H7A	0.3627	0.3669	1.0288	0.0975
H7B	0.5334	0.3763	0.9280	0.0975
H7C	0.3029	0.4749	0.9265	0.0975
H8A	0.3719	0.1461	0.9866	0.1320
H8B	0.3441	0.1321	0.8581	0.1320
H8C	0.5548	0.1662	0.8954	0.1320
H9A	−0.0383	0.4249	0.8915	0.1097
H9B	−0.0369	0.2979	0.8569	0.1097
H9C	0.0035	0.3082	0.9849	0.1097

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
S1	0.0982 (5)	0.0829 (5)	0.0520 (4)	−0.0559 (4)	−0.0008 (3)	−0.0013 (3)
O1	0.077 (1)	0.0673 (10)	0.0470 (9)	−0.0403 (9)	−0.0046 (7)	−0.0074 (7)
O2	0.112 (1)	0.116 (2)	0.050 (1)	−0.073 (1)	0.0067 (9)	−0.0140 (9)
O3	0.079 (1)	0.082 (1)	0.0459 (9)	−0.0475 (9)	0.0074 (7)	−0.0172 (8)
O4	0.101 (1)	0.075 (1)	0.0538 (10)	−0.056 (1)	0.0000 (8)	−0.0064 (8)
N1	0.079 (1)	0.069 (1)	0.046 (1)	−0.043 (1)	0.0024 (9)	−0.0100 (8)
N2	0.080 (1)	0.066 (1)	0.048 (1)	−0.043 (1)	0.0031 (9)	−0.0121 (9)
C1	0.086 (2)	0.102 (2)	0.063 (2)	−0.041 (2)	−0.017 (1)	−0.005 (1)
C2	0.085 (2)	0.093 (2)	0.113 (3)	−0.027 (2)	0.000 (2)	−0.044 (2)
C3	0.087 (2)	0.080 (2)	0.074 (2)	−0.047 (2)	−0.009 (1)	−0.009 (1)
C4	0.066 (2)	0.063 (1)	0.056 (1)	−0.028 (1)	−0.009 (1)	−0.015 (1)
C5	0.068 (2)	0.065 (1)	0.048 (1)	−0.029 (1)	−0.002 (1)	−0.008 (1)
C6	0.062 (1)	0.056 (1)	0.050 (1)	−0.025 (1)	0.0003 (10)	−0.0107 (10)
C7	0.090 (2)	0.105 (2)	0.061 (2)	−0.040 (2)	−0.002 (1)	−0.025 (1)
C8	0.149 (3)	0.083 (2)	0.089 (2)	−0.012 (2)	−0.035 (2)	−0.009 (2)
C9	0.081 (2)	0.143 (3)	0.058 (2)	−0.046 (2)	0.012 (1)	−0.014 (2)
C10	0.065 (1)	0.070 (2)	0.045 (1)	−0.024 (1)	0.001 (1)	−0.009 (1)
C11	0.066 (1)	0.060 (1)	0.049 (1)	−0.029 (1)	0.003 (1)	−0.012 (1)

Geometric parameters (Å, º)

S1—C6	1.637 (2)	C2—H2B	0.950
O1—C4	1.487 (3)	C2—H2C	0.950
O1—C5	1.337 (3)	C3—C4	1.508 (4)
O2—C5	1.179 (3)	C3—H3A	0.950
O3—C10	1.477 (3)	C3—H3B	0.950
O3—C11	1.323 (3)	C3—H3C	0.950
O4—C11	1.203 (3)	C7—C10	1.514 (4)
N1—C5	1.402 (3)	C7—H7A	0.950
N1—C6	1.364 (3)	C7—H7B	0.950
N1—H1N	0.870	C7—H7C	0.950
N2—C6	1.380 (3)	C8—C10	1.505 (4)
N2—C11	1.383 (3)	C8—H8A	0.950
N2—H2N	0.870	C8—H8B	0.950
C1—C4	1.508 (3)	C8—H8C	0.950
C1—H1A	0.950	C9—C10	1.495 (4)
C1—H1B	0.950	C9—H9A	0.950
C1—H1C	0.950	C9—H9B	0.950
C2—C4	1.500 (4)	C9—H9C	0.950
C2—H2A	0.950
C4—O1—C5	121.1 (2)	O1—C5—N1	105.3 (2)
C10—O3—C11	121.9 (2)	O2—C5—N1	126.5 (2)
C5—N1—C6	127.5 (2)	S1—C6—N1	127.3 (2)
C5—N1—H1N	116.2	S1—C6—N2	119.5 (2)
C6—N1—H1N	116.2	N1—C6—N2	113.2 (2)
C6—N2—C11	129.4 (2)	C10—C7—H7A	109.5
C6—N2—H2N	115.3	C10—C7—H7B	109.5
C11—N2—H2N	115.3	C10—C7—H7C	109.5
C4—C1—H1A	109.5	H7A—C7—H7B	109.5
C4—C1—H1B	109.5	H7A—C7—H7C	109.5
C4—C1—H1C	109.5	H7B—C7—H7C	109.5
H1A—C1—H1B	109.5	C10—C8—H8A	109.5
H1A—C1—H1C	109.5	C10—C8—H8B	109.5
H1B—C1—H1C	109.5	C10—C8—H8C	109.5
C4—C2—H2A	109.5	H8A—C8—H8B	109.5
C4—C2—H2B	109.5	H8A—C8—H8C	109.5
C4—C2—H2C	109.5	H8B—C8—H8C	109.5
H2A—C2—H2B	109.5	C10—C9—H9A	109.5
H2A—C2—H2C	109.5	C10—C9—H9B	109.5
H2B—C2—H2C	109.5	C10—C9—H9C	109.5
C4—C3—H3A	109.5	H9A—C9—H9B	109.5
C4—C3—H3B	109.5	H9A—C9—H9C	109.5
C4—C3—H3C	109.5	H9B—C9—H9C	109.5
H3A—C3—H3B	109.5	O3—C10—C7	102.0 (2)
H3A—C3—H3C	109.5	O3—C10—C8	109.4 (2)
H3B—C3—H3C	109.5	O3—C10—C9	109.6 (2)
O1—C4—C1	110.6 (2)	C7—C10—C8	111.6 (2)
O1—C4—C2	108.7 (2)	C7—C10—C9	110.4 (2)
O1—C4—C3	101.8 (2)	C8—C10—C9	113.2 (3)
C1—C4—C2	113.1 (2)	O3—C11—O4	127.0 (2)
C1—C4—C3	110.2 (2)	O3—C11—N2	107.9 (2)
C2—C4—C3	111.8 (2)	O4—C11—N2	125.0 (2)
O1—C5—O2	128.2 (2)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1N···O4	0.87	1.96	2.658 (3)	137
N2—H2N···S1^i	0.87	2.56	3.395 (2)	162
C1—H1A···O2	0.95	2.37	2.980 (4)	122
C2—H2C···O2	0.95	2.54	3.117 (4)	119
C8—H8B···O4	0.95	2.51	3.093 (5)	120
C9—H9B···O4	0.95	2.35	2.962 (3)	122

Symmetry code: (i) −x+1, −y+1, −z+1.