N-Benzoyl-N′-(2-{2-[2-(N-benzoyl­thio­ureido)phen­oxy]eth­oxy}phen­yl)thio­urea

The mol­ecule of the title compound, C₃₀H₂₆N₄O₄S₂, has an inversion centre. The mol­ecule is planar, with a mean devation of 0.179 Å from the least-squares plane defined by the 40 constituent atoms (excluding H atoms). The crystal structure has inversion-related inter­molecular N—H...S hydrogen bonds and intra­molecular N—H...O hydrogen bonds.

Key indicators

• Single-crystal X-ray study
• T = 294 K
• Mean [sigma](C-C) = 0.004 Å
• R factor = 0.069
• wR factor = 0.188
• Data-to-parameter ratio = 13.7

checkCIF/PLATON results

No syntax errors found



Alert level B
RINTA01_ALERT_3_B  The value of Rint is greater than 0.15
            Rint given   0.170
PLAT020_ALERT_3_B The value of Rint is greater than 0.10 .........       0.17

Alert level C
PLAT250_ALERT_2_C Large U3/U1 Ratio for Average U(i,j) Tensor ....       2.50
PLAT720_ALERT_4_C Number of Unusual/Non-Standard Label(s) ........          2

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

   0 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
   1 ALERT type 2 Indicator that the structure model may be wrong or deficient
   2 ALERT type 3 Indicator that the structure quality may be low
   1 ALERT type 4 Improvement, methodology, query or suggestion
   0 ALERT type 5 Informative message, check

---

Computing details

Data collection: SMART (Bruker, 1998); cell refinement: SAINT (Bruker, 1998); data reduction: SAINT; program(s) used to solve structure: SHELXTL (Sheldrick, 1997); program(s) used to refine structure: SHELXTL; molecular graphics: ORTEP-3 (Farrugia, 1997) and DIAMOND (Brandenburg, 1998); software used to prepare material for publication: SHELXTL.

N-Benzoyl-N'-(2-{2-[2-(N-benzoylthioureido)phenoxy]ethoxy}phenyl)thiourea

Crystal data

C30H26N4O4S2	F(000) = 596
Mr = 570.67	Dx = 1.336 Mg m^−3
Monoclinic, P21/n	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -p_2yn	Cell parameters from 2068 reflections
a = 14.1248 (7) Å	θ = 3.0–26.5°
b = 5.5175 (3) Å	µ = 0.23 mm^−1
c = 19.179 (1) Å	T = 294 K
β = 108.408 (2)°	Block, colourless
V = 1418.21 (13) Å^3	0.39 × 0.23 × 0.08 mm
Z = 2

Data collection

Bruker SMART CCD area-detector diffractometer	1689 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	Rint = 0.170
Graphite monochromator	θmax = 25.0°, θmin = 2.2°
Detector resolution: 10.00 pixels mm^-1	h = −14→16
φ and ω scans	k = −6→6
6813 measured reflections	l = −21→22
2485 independent reflections

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)] = 0.069	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.188	H-atom parameters constrained
S = 0.95	w = 1/[σ^2(Fo^2) + (0.0891P)^2] where P = (Fo^2 + 2Fc^2)/3
2485 reflections	(Δ/σ)max < 0.001
181 parameters	Δρmax = 0.40 e Å^−3
0 restraints	Δρmin = −0.40 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
S	0.48978 (5)	0.17436 (18)	0.09278 (4)	0.0734 (4)
O1	0.16747 (13)	−0.0118 (3)	−0.03308 (10)	0.0618 (6)
O2	0.12806 (13)	0.4622 (4)	0.05001 (11)	0.0649 (6)
N1	0.33694 (15)	−0.0512 (4)	0.00232 (12)	0.0537 (6)
H1N1	0.3840	−0.1339	−0.0058	0.064*
N2	0.29423 (15)	0.2477 (4)	0.07012 (12)	0.0496 (6)
H2N2	0.2355	0.1950	0.0466	0.060*
C1	0.2323 (2)	−0.3102 (5)	−0.09469 (15)	0.0517 (7)
C2	0.3056 (2)	−0.4829 (5)	−0.09043 (17)	0.0586 (8)
H2	0.3647	−0.4790	−0.0513	0.070*
C3	0.2920 (3)	−0.6585 (5)	−0.1431 (2)	0.0697 (9)
H3	0.3421	−0.7713	−0.1401	0.084*
C4	0.2036 (3)	−0.6677 (6)	−0.2008 (2)	0.0772 (10)
H4	0.1940	−0.7878	−0.2364	0.093*
C5	0.1306 (3)	−0.5013 (6)	−0.2056 (2)	0.0820 (11)
H5	0.0716	−0.5069	−0.2448	0.098*
C6	0.1442 (2)	−0.3242 (6)	−0.15244 (18)	0.0709 (9)
H6	0.0935	−0.2132	−0.1555	0.085*
C7	0.29591 (18)	0.4453 (5)	0.11721 (14)	0.0475 (7)
C8	0.20437 (18)	0.5646 (5)	0.10427 (14)	0.0492 (7)
C9	0.1968 (2)	0.7652 (6)	0.14449 (16)	0.0621 (8)
H9	0.1361	0.8454	0.1348	0.074*
C10	0.2801 (2)	0.8479 (6)	0.19963 (17)	0.0670 (9)
H10	0.2756	0.9844	0.2269	0.080*
C11	0.3673 (2)	0.7298 (7)	0.21351 (18)	0.0750 (10)
H11	0.4224	0.7846	0.2513	0.090*
C12	0.3775 (2)	0.5302 (6)	0.17347 (18)	0.0678 (9)
H12	0.4388	0.4523	0.1841	0.081*
C14	0.24112 (19)	−0.1160 (5)	−0.03972 (15)	0.0507 (7)
C13	0.36826 (19)	0.1287 (5)	0.05589 (14)	0.0492 (7)
C15	0.03241 (18)	0.5768 (6)	0.03060 (16)	0.0586 (8)
H15A	0.0360	0.7417	0.0141	0.070*
H15B	0.0070	0.5793	0.0720	0.070*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
S	0.0188 (4)	0.1374 (9)	0.0584 (5)	0.0027 (4)	0.0041 (4)	−0.0124 (4)
O1	0.0228 (10)	0.0969 (15)	0.0622 (12)	0.0031 (9)	0.0084 (9)	−0.0125 (10)
O2	0.0243 (10)	0.0948 (15)	0.0609 (12)	0.0137 (9)	−0.0076 (9)	−0.0175 (10)
N1	0.0229 (11)	0.0876 (16)	0.0484 (12)	0.0092 (11)	0.0082 (10)	0.0013 (12)
N2	0.0189 (11)	0.0802 (15)	0.0471 (12)	−0.0023 (10)	0.0067 (10)	−0.0005 (11)
C1	0.0355 (15)	0.0675 (18)	0.0523 (16)	0.0025 (12)	0.0140 (13)	0.0075 (13)
C2	0.0456 (17)	0.0677 (19)	0.0623 (17)	0.0053 (14)	0.0172 (15)	0.0184 (15)
C3	0.066 (2)	0.0618 (19)	0.088 (2)	0.0141 (15)	0.035 (2)	0.0076 (17)
C4	0.075 (3)	0.080 (2)	0.081 (2)	−0.0023 (19)	0.031 (2)	−0.0134 (18)
C5	0.053 (2)	0.108 (3)	0.078 (2)	0.002 (2)	0.0109 (19)	−0.026 (2)
C6	0.0366 (17)	0.099 (2)	0.069 (2)	0.0088 (15)	0.0052 (16)	−0.0181 (18)
C7	0.0273 (13)	0.0719 (17)	0.0396 (13)	−0.0040 (12)	0.0054 (11)	0.0050 (13)
C8	0.0279 (14)	0.0702 (17)	0.0421 (14)	−0.0024 (12)	0.0003 (12)	0.0029 (13)
C9	0.0476 (18)	0.0756 (19)	0.0552 (16)	0.0053 (15)	0.0051 (15)	−0.0009 (15)
C10	0.055 (2)	0.081 (2)	0.0590 (18)	−0.0104 (16)	0.0098 (16)	−0.0090 (15)
C11	0.0424 (19)	0.109 (3)	0.0624 (19)	−0.0237 (18)	0.0004 (16)	−0.0206 (19)
C12	0.0250 (14)	0.112 (3)	0.0590 (17)	−0.0082 (15)	0.0022 (14)	−0.0093 (17)
C14	0.0264 (14)	0.0748 (18)	0.0488 (15)	0.0033 (12)	0.0089 (12)	0.0077 (13)
C13	0.0243 (13)	0.0821 (19)	0.0386 (13)	0.0043 (13)	0.0060 (11)	0.0066 (13)
C15	0.0206 (13)	0.090 (2)	0.0571 (16)	0.0107 (13)	0.0011 (12)	−0.0095 (15)

Geometric parameters (Å, º)

S—C13	1.656 (3)	C4—H4	0.9300
O1—C14	1.230 (3)	C5—C6	1.381 (4)
O2—C8	1.362 (3)	C5—H5	0.9300
O2—C15	1.430 (3)	C6—H6	0.9300
N1—C14	1.386 (3)	C7—C12	1.388 (4)
N1—C13	1.396 (4)	C7—C8	1.401 (4)
N1—H1N1	0.8600	C8—C9	1.373 (4)
N2—C13	1.334 (3)	C9—C10	1.388 (4)
N2—C7	1.411 (3)	C9—H9	0.9300
N2—H2N2	0.8600	C10—C11	1.344 (5)
C1—C6	1.383 (4)	C10—H10	0.9300
C1—C2	1.390 (4)	C11—C12	1.376 (4)
C1—C14	1.481 (4)	C11—H11	0.9300
C2—C3	1.369 (4)	C12—H12	0.9300
C2—H2	0.9300	C15—C15^i	1.502 (5)
C3—C4	1.383 (5)	C15—H15A	0.9700
C3—H3	0.9300	C15—H15B	0.9700
C4—C5	1.361 (4)
C8—O2—C15	118.0 (2)	O2—C8—C9	125.5 (2)
C14—N1—C13	129.5 (2)	O2—C8—C7	113.8 (3)
C14—N1—H1N1	115.3	C9—C8—C7	120.7 (3)
C13—N1—H1N1	115.3	C8—C9—C10	119.7 (3)
C13—N2—C7	131.0 (2)	C8—C9—H9	120.2
C13—N2—H2N2	114.5	C10—C9—H9	120.2
C7—N2—H2N2	114.5	C11—C10—C9	119.7 (3)
C6—C1—C2	118.3 (3)	C11—C10—H10	120.1
C6—C1—C14	117.6 (2)	C9—C10—H10	120.1
C2—C1—C14	124.1 (3)	C10—C11—C12	121.9 (3)
C3—C2—C1	120.9 (3)	C10—C11—H11	119.0
C3—C2—H2	119.6	C12—C11—H11	119.0
C1—C2—H2	119.6	C11—C12—C7	119.8 (3)
C2—C3—C4	119.8 (3)	C11—C12—H12	120.1
C2—C3—H3	120.1	C7—C12—H12	120.1
C4—C3—H3	120.1	O1—C14—N1	121.5 (3)
C5—C4—C3	120.2 (3)	O1—C14—C1	121.9 (2)
C5—C4—H4	119.9	N1—C14—C1	116.6 (2)
C3—C4—H4	119.9	N2—C13—N1	114.4 (2)
C4—C5—C6	120.1 (3)	N2—C13—S	127.7 (2)
C4—C5—H5	120.0	N1—C13—S	117.86 (19)
C6—C5—H5	120.0	O2—C15—C15^i	104.3 (3)
C5—C6—C1	120.7 (3)	O2—C15—H15A	110.9
C5—C6—H6	119.6	C15^i—C15—H15A	110.9
C1—C6—H6	119.6	O2—C15—H15B	110.9
C12—C7—C8	118.2 (3)	C15^i—C15—H15B	110.9
C12—C7—N2	126.9 (3)	H15A—C15—H15B	108.9
C8—C7—N2	114.9 (2)

Symmetry code: (i) −x, −y+1, −z.

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1N1···S^ii	0.86	2.81	3.549 (2)	145
N2—H2N2···O1	0.86	1.91	2.634 (3)	141
N2—H2N2···O2	0.86	2.13	2.547 (3)	109

Symmetry code: (ii) −x+1, −y, −z.