3,3'-Dibenzoyl-1,1'-(3,6-dioxaoctane-1,8-di-yl)dithio-urea.

In the mol-ecule of the title compound, C(22)H(26)N(4)O(4)S(2), the central O-CH(2)-CH(2)-O chain adopts a synclinal conformation [torsion angle = 65.0 (2)°]. The crystal structure is stabilized by intra-molecular N-H⋯O=C and inter-molecular N-H⋯O-C hydrogen bonds.

Related literature

For related structures, see: Avşar et al. (2003 ▶); Arslan et al. (2004 ▶); Du & Du (2008 ▶); Ding et al. (2008 ▶).

Experimental

Crystal data

C22H26N4O4S2

M = 474.59

Triclinic,

a = 7.9718 (2) Å

b = 9.2177 (3) Å

c = 16.4106 (5) Å

α = 81.018 (2)°

β = 83.364 (2)°

γ = 80.450 (2)°

V = 1169.60 (6) Å3

Z = 2

Mo Kα radiation

μ = 0.26 mm−1

T = 293 K

0.10 × 0.10 × 0.10 mm

Data collection

Nonius Kappa CCD diffractometer

Absorption correction: none

7989 measured reflections

4211 independent reflections

2737 reflections with I > 2σ(I)

R int = 0.030

Refinement

R[F 2 > 2σ(F 2)] = 0.045

wR(F 2) = 0.128

S = 1.02

4211 reflections

305 parameters

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.41 e Å−3

Δρmin = −0.50 e Å−3

Data collection: COLLECT (Nonius, 1998 ▶); cell refinement: DENZO and SCALEPACK (Otwinowski & Minor, 1997 ▶); data reduction: DENZO and SCALEPACK; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: PLATON (Spek, 2009 ▶); software used to prepare material for publication: SHELXL97.

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536809005662/bh2217sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536809005662/bh2217Isup2.hkl

Additional supplementary materials: crystallographic information; 3D view; checkCIF report

C22H26N4O4S2	Z = 2
Mr = 474.59	F(000) = 500
Triclinic, P1	Dx = 1.347 Mg m−3
Hall symbol: -P 1	Melting point: 415 K
a = 7.9718 (2) Å	Mo Kα radiation, λ = 0.71073 Å
b = 9.2177 (3) Å	Cell parameters from 4206 reflections
c = 16.4106 (5) Å	θ = 1.0–25.4°
α = 81.018 (2)°	µ = 0.26 mm−1
β = 83.364 (2)°	T = 293 K
γ = 80.450 (2)°	Prism, yellow
V = 1169.60 (6) Å3	0.10 × 0.10 × 0.10 mm

Nonius KappaCCD diffractometer	2737 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	Rint = 0.030
graphite	θmax = 25.2°, θmin = 2.3°
ω scans	h = −9→9
7989 measured reflections	k = −11→11
4211 independent reflections	l = −19→19

Refinement on F2	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.045	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.128	H atoms treated by a mixture of independent and constrained refinement
S = 1.02	w = 1/[σ2(Fo2) + (0.0614P)2 + 0.2609P] where P = (Fo2 + 2Fc2)/3
4211 reflections	(Δ/σ)max = 0.008
305 parameters	Δρmax = 0.41 e Å−3
0 restraints	Δρmin = −0.50 e Å−3
0 constraints

	x	y	z	Uiso*/Ueq
S1	0.37094 (10)	0.16706 (9)	0.86251 (5)	0.0713 (3)
S2	1.26452 (13)	−0.27342 (8)	0.52516 (4)	0.0790 (3)
O1	0.7377 (3)	0.4586 (2)	0.91685 (11)	0.0711 (6)
O2	0.81088 (19)	0.39803 (17)	0.67050 (9)	0.0482 (4)
O3	1.12041 (19)	0.24744 (17)	0.60508 (10)	0.0472 (4)
O4	1.2463 (3)	0.1608 (2)	0.35665 (11)	0.0740 (6)
N1	0.5641 (3)	0.2839 (3)	0.94678 (14)	0.0527 (6)
H1	0.530 (3)	0.224 (3)	0.9815 (16)	0.049 (8)*
N2	0.5680 (3)	0.3729 (2)	0.80784 (13)	0.0492 (5)
H2	0.639 (3)	0.422 (3)	0.8172 (16)	0.056 (8)*
N3	1.2498 (3)	0.0165 (3)	0.50822 (13)	0.0506 (5)
H3	1.236 (3)	0.099 (3)	0.4798 (17)	0.063 (9)*
N4	1.2073 (3)	−0.0786 (2)	0.39123 (12)	0.0465 (5)
H4	1.190 (3)	−0.154 (3)	0.3741 (15)	0.052 (8)*
C1	0.7116 (3)	0.3433 (3)	1.05616 (14)	0.0456 (6)
C2	0.8101 (3)	0.4370 (3)	1.08034 (16)	0.0539 (6)
H2A	0.8497	0.5115	1.0416	0.065*
C3	0.8498 (4)	0.4211 (3)	1.16088 (18)	0.0639 (7)
H3A	0.9169	0.4840	1.1763	0.077*
C4	0.7902 (4)	0.3120 (3)	1.21864 (18)	0.0692 (8)
H4A	0.8165	0.3012	1.2732	0.083*
C5	0.6923 (4)	0.2194 (4)	1.19573 (19)	0.0771 (9)
H5	0.6513	0.1464	1.2350	0.093*
C6	0.6537 (4)	0.2335 (3)	1.11472 (17)	0.0649 (8)
H6	0.5885	0.1690	1.0995	0.078*
C7	0.6744 (3)	0.3674 (3)	0.96796 (15)	0.0488 (6)
C8	0.5078 (3)	0.2817 (3)	0.86956 (15)	0.0477 (6)
C9	0.5275 (3)	0.3838 (3)	0.72324 (15)	0.0537 (6)
H9A	0.4095	0.4293	0.7189	0.064*
H9B	0.5406	0.2851	0.7075	0.064*
C10	0.6419 (3)	0.4745 (3)	0.66582 (15)	0.0516 (6)
H10A	0.6101	0.4859	0.6096	0.062*
H10B	0.6331	0.5723	0.6822	0.062*
C11	0.9346 (3)	0.4733 (3)	0.61860 (16)	0.0522 (6)
H11A	0.9278	0.5730	0.6320	0.063*
H11B	0.9133	0.4804	0.5610	0.063*
C12	1.1067 (3)	0.3882 (3)	0.63208 (16)	0.0506 (6)
H12A	1.1936	0.4426	0.6014	0.061*
H12B	1.1243	0.3751	0.6904	0.061*
C13	1.2832 (3)	0.1611 (3)	0.61572 (16)	0.0529 (6)
H13A	1.3092	0.1538	0.6727	0.063*
H13B	1.3705	0.2077	0.5799	0.063*
C14	1.2803 (3)	0.0091 (3)	0.59436 (14)	0.0504 (6)
H14A	1.3887	−0.0529	0.6045	0.061*
H14B	1.1912	−0.0359	0.6297	0.061*
C15	1.2389 (3)	−0.1016 (3)	0.47501 (14)	0.0447 (6)
C16	1.2118 (3)	0.0483 (3)	0.33592 (14)	0.0454 (6)
C17	1.1796 (3)	0.0433 (2)	0.24907 (14)	0.0419 (5)
C18	1.2227 (3)	0.1595 (3)	0.19018 (15)	0.0527 (6)
H18	1.2684	0.2361	0.2062	0.063*
C19	1.1984 (3)	0.1624 (3)	0.10851 (16)	0.0610 (7)
H19	1.2299	0.2398	0.0693	0.073*
C20	1.1281 (3)	0.0520 (3)	0.08436 (16)	0.0618 (7)
H20	1.1120	0.0546	0.0289	0.074*
C21	1.0811 (3)	−0.0632 (3)	0.14224 (16)	0.0605 (7)
H21	1.0324	−0.1378	0.1260	0.073*
C22	1.1069 (3)	−0.0672 (3)	0.22467 (15)	0.0507 (6)
H22	1.0751	−0.1446	0.2638	0.061*

	U11	U22	U33	U12	U13	U23
S1	0.0807 (5)	0.0781 (5)	0.0659 (5)	−0.0445 (4)	−0.0032 (4)	−0.0115 (4)
S2	0.1467 (8)	0.0464 (4)	0.0494 (4)	−0.0296 (5)	−0.0275 (5)	0.0059 (3)
O1	0.0906 (14)	0.0822 (14)	0.0503 (11)	−0.0502 (12)	−0.0123 (10)	0.0050 (10)
O2	0.0498 (10)	0.0443 (9)	0.0461 (9)	−0.0077 (8)	0.0014 (8)	0.0036 (7)
O3	0.0497 (10)	0.0457 (9)	0.0501 (10)	−0.0119 (8)	−0.0053 (7)	−0.0140 (8)
O4	0.1328 (18)	0.0430 (11)	0.0518 (11)	−0.0288 (11)	−0.0176 (11)	−0.0010 (9)
N1	0.0584 (14)	0.0572 (14)	0.0453 (13)	−0.0237 (11)	0.0023 (11)	−0.0054 (11)
N2	0.0468 (12)	0.0626 (14)	0.0431 (12)	−0.0214 (11)	0.0000 (10)	−0.0112 (10)
N3	0.0716 (15)	0.0397 (13)	0.0409 (12)	−0.0077 (11)	−0.0081 (10)	−0.0055 (10)
N4	0.0666 (14)	0.0372 (12)	0.0385 (11)	−0.0162 (10)	−0.0079 (9)	−0.0024 (9)
C1	0.0450 (13)	0.0445 (14)	0.0455 (14)	−0.0027 (11)	−0.0034 (11)	−0.0053 (11)
C2	0.0562 (15)	0.0556 (16)	0.0514 (15)	−0.0127 (13)	−0.0023 (12)	−0.0093 (12)
C3	0.0698 (18)	0.0677 (18)	0.0579 (17)	−0.0074 (15)	−0.0134 (14)	−0.0177 (15)
C4	0.076 (2)	0.078 (2)	0.0507 (17)	0.0048 (17)	−0.0169 (15)	−0.0081 (16)
C5	0.087 (2)	0.080 (2)	0.0591 (19)	−0.0181 (18)	−0.0171 (16)	0.0192 (16)
C6	0.0748 (19)	0.0598 (17)	0.0612 (18)	−0.0203 (15)	−0.0184 (15)	0.0077 (14)
C7	0.0483 (14)	0.0492 (15)	0.0496 (15)	−0.0124 (12)	−0.0012 (12)	−0.0062 (12)
C8	0.0461 (13)	0.0507 (15)	0.0486 (15)	−0.0121 (11)	0.0023 (11)	−0.0135 (12)
C9	0.0498 (15)	0.0667 (17)	0.0491 (15)	−0.0132 (13)	−0.0048 (12)	−0.0167 (13)
C10	0.0562 (15)	0.0521 (15)	0.0451 (14)	−0.0026 (12)	−0.0084 (12)	−0.0056 (12)
C11	0.0639 (16)	0.0404 (14)	0.0514 (15)	−0.0188 (12)	0.0041 (12)	0.0006 (11)
C12	0.0578 (15)	0.0444 (14)	0.0527 (15)	−0.0208 (12)	0.0023 (12)	−0.0082 (12)
C13	0.0527 (15)	0.0607 (16)	0.0485 (15)	−0.0100 (13)	−0.0065 (12)	−0.0144 (12)
C14	0.0612 (16)	0.0531 (15)	0.0379 (13)	−0.0040 (12)	−0.0102 (11)	−0.0100 (11)
C15	0.0512 (14)	0.0442 (14)	0.0399 (13)	−0.0115 (11)	−0.0051 (11)	−0.0044 (11)
C16	0.0543 (14)	0.0392 (14)	0.0426 (13)	−0.0097 (11)	−0.0041 (11)	−0.0023 (11)
C17	0.0440 (13)	0.0396 (13)	0.0399 (13)	−0.0052 (10)	−0.0027 (10)	−0.0009 (10)
C18	0.0591 (16)	0.0488 (15)	0.0492 (15)	−0.0153 (12)	−0.0033 (12)	0.0029 (12)
C19	0.0667 (18)	0.0656 (18)	0.0458 (16)	−0.0163 (15)	−0.0043 (13)	0.0132 (13)
C20	0.0631 (17)	0.080 (2)	0.0399 (14)	−0.0112 (15)	−0.0098 (13)	0.0033 (14)
C21	0.0691 (17)	0.0629 (17)	0.0527 (16)	−0.0161 (14)	−0.0134 (13)	−0.0059 (13)
C22	0.0572 (15)	0.0500 (15)	0.0434 (14)	−0.0135 (12)	−0.0065 (12)	0.0052 (11)

S1—C8	1.665 (3)	C5—H5	0.9300
S2—C15	1.659 (2)	C6—H6	0.9300
O1—C7	1.220 (3)	C9—C10	1.492 (3)
O2—C10	1.417 (3)	C9—H9A	0.9700
O2—C11	1.424 (3)	C9—H9B	0.9700
O3—C12	1.419 (3)	C10—H10A	0.9700
O3—C13	1.419 (3)	C10—H10B	0.9700
O4—C16	1.222 (3)	C11—C12	1.485 (3)
N1—C7	1.366 (3)	C11—H11A	0.9700
N1—C8	1.396 (3)	C11—H11B	0.9700
N1—H1	0.79 (3)	C12—H12A	0.9700
N2—C8	1.311 (3)	C12—H12B	0.9700
N2—C9	1.446 (3)	C13—C14	1.501 (3)
N2—H2	0.82 (3)	C13—H13A	0.9700
N3—C15	1.310 (3)	C13—H13B	0.9700
N3—C14	1.451 (3)	C14—H14A	0.9700
N3—H3	0.83 (3)	C14—H14B	0.9700
N4—C16	1.367 (3)	C16—C17	1.486 (3)
N4—C15	1.404 (3)	C17—C22	1.382 (3)
N4—H4	0.82 (3)	C17—C18	1.386 (3)
C1—C6	1.382 (3)	C18—C19	1.372 (4)
C1—C2	1.387 (3)	C18—H18	0.9300
C1—C7	1.486 (3)	C19—C20	1.369 (4)
C2—C3	1.375 (4)	C19—H19	0.9300
C2—H2A	0.9300	C20—C21	1.380 (4)
C3—C4	1.376 (4)	C20—H20	0.9300
C3—H3A	0.9300	C21—C22	1.386 (4)
C4—C5	1.366 (4)	C21—H21	0.9300
C4—H4A	0.9300	C22—H22	0.9300
C5—C6	1.381 (4)
C10—O2—C11	113.12 (18)	H10A—C10—H10B	108.5
C12—O3—C13	112.15 (18)	O2—C11—C12	108.43 (19)
C7—N1—C8	129.4 (2)	O2—C11—H11A	110.0
C7—N1—H1	117.6 (19)	C12—C11—H11A	110.0
C8—N1—H1	112.9 (19)	O2—C11—H11B	110.0
C8—N2—C9	124.1 (2)	C12—C11—H11B	110.0
C8—N2—H2	117.9 (18)	H11A—C11—H11B	108.4
C9—N2—H2	117.9 (19)	O3—C12—C11	109.5 (2)
C15—N3—C14	122.6 (2)	O3—C12—H12A	109.8
C15—N3—H3	119 (2)	C11—C12—H12A	109.8
C14—N3—H3	118 (2)	O3—C12—H12B	109.8
C16—N4—C15	127.9 (2)	C11—C12—H12B	109.8
C16—N4—H4	118.1 (18)	H12A—C12—H12B	108.2
C15—N4—H4	113.8 (18)	O3—C13—C14	108.6 (2)
C6—C1—C2	118.7 (2)	O3—C13—H13A	110.0
C6—C1—C7	123.7 (2)	C14—C13—H13A	110.0
C2—C1—C7	117.6 (2)	O3—C13—H13B	110.0
C3—C2—C1	120.8 (3)	C14—C13—H13B	110.0
C3—C2—H2A	119.6	H13A—C13—H13B	108.4
C1—C2—H2A	119.6	N3—C14—C13	111.0 (2)
C2—C3—C4	119.8 (3)	N3—C14—H14A	109.4
C2—C3—H3A	120.1	C13—C14—H14A	109.4
C4—C3—H3A	120.1	N3—C14—H14B	109.4
C5—C4—C3	119.9 (3)	C13—C14—H14B	109.4
C5—C4—H4A	120.0	H14A—C14—H14B	108.0
C3—C4—H4A	120.0	N3—C15—N4	116.7 (2)
C4—C5—C6	120.5 (3)	N3—C15—S2	124.06 (19)
C4—C5—H5	119.7	N4—C15—S2	119.18 (18)
C6—C5—H5	119.7	O4—C16—N4	121.1 (2)
C5—C6—C1	120.2 (3)	O4—C16—C17	121.1 (2)
C5—C6—H6	119.9	N4—C16—C17	117.8 (2)
C1—C6—H6	119.9	C22—C17—C18	119.0 (2)
O1—C7—N1	121.3 (2)	C22—C17—C16	124.1 (2)
O1—C7—C1	121.7 (2)	C18—C17—C16	116.9 (2)
N1—C7—C1	117.0 (2)	C19—C18—C17	120.5 (3)
N2—C8—N1	116.1 (2)	C19—C18—H18	119.8
N2—C8—S1	125.2 (2)	C17—C18—H18	119.8
N1—C8—S1	118.66 (18)	C20—C19—C18	120.4 (2)
N2—C9—C10	110.6 (2)	C20—C19—H19	119.8
N2—C9—H9A	109.5	C18—C19—H19	119.8
C10—C9—H9A	109.5	C19—C20—C21	120.1 (3)
N2—C9—H9B	109.5	C19—C20—H20	120.0
C10—C9—H9B	109.5	C21—C20—H20	120.0
H9A—C9—H9B	108.1	C20—C21—C22	119.7 (3)
O2—C10—C9	107.14 (19)	C20—C21—H21	120.1
O2—C10—H10A	110.3	C22—C21—H21	120.1
C9—C10—H10A	110.3	C17—C22—C21	120.3 (2)
O2—C10—H10B	110.3	C17—C22—H22	119.8
C9—C10—H10B	110.3	C21—C22—H22	119.8
O2—C11—C12—O3	65.0 (2)

D—H···A	D—H	H···A	D···A	D—H···A
N2—H2···O1	0.82 (3)	1.99 (3)	2.648 (3)	136 (2)
N3—H3···O4	0.83 (3)	2.01 (3)	2.632 (3)	132 (3)
N4—H4···O2i	0.82 (3)	2.48 (3)	3.290 (3)	170 (2)

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N2—H2⋯O1	0.82 (3)	1.99 (3)	2.648 (3)	136 (2)
N3—H3⋯O4	0.83 (3)	2.01 (3)	2.632 (3)	132 (3)
N4—H4⋯O2i	0.82 (3)	2.48 (3)	3.290 (3)	170 (2)

Symmetry code: (i) .