N-(2,4-Dichloro­phenoxy­acet­yl)-N′-(4-nitro­phen­yl)thio­urea

Li, Q.-J.; Yang, C.-L.; Xie, X.-Q.; Luo, J.-X.

doi:10.1107/S1600536806033010

N-(2,4-Dichlorophenoxyacetyl)-N′-(4-nitrophenyl)thiourea

Q.-J. Li, C.-L. Yang, X.-Q. Xie and J.-X. Luo

In the crystal structure of the title compound, C₁₅H₁₁Cl₂N₃O₄S, there are two intramolecular N—H

O and one C—H

S hydrogen bonds and a weak intermolecular C—H

O hydrogen bond.

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Supporting information

	Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536806033010/bx2018sup1.cif Contains datablocks global, I
	Structure factor file (CIF format) https://doi.org/10.1107/S1600536806033010/bx2018Isup2.hkl Contains datablock I

CCDC reference: 620724

checkCIF report

Key indicators

Single-crystal X-ray study
T = 293 K
Mean (C-C) = 0.006 Å
R factor = 0.064
wR factor = 0.170
Data-to-parameter ratio = 14.7

checkCIF/PLATON results

No syntax errors found



Alert level C
PLAT340_ALERT_3_C Low Bond Precision on C-C bonds (x 1000) Ang ...          6
PLAT431_ALERT_2_C Short Inter HL..A Contact  Cl1    ..  O3      ..       3.24 Ang.

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
   2 ALERT level C = Check and explain
   2 ALERT level G = General alerts; check

   2 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
   1 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

Computing details top

Data collection: CAD-4 Software (Enraf–Nonius, 1989); cell refinement: CAD-4 Software; data reduction: XCAD4 (Harms & Wocadlo, 1995); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: SHELXTL (Bruker, 1998); software used to prepare material for publication: SHELXTL.

N-(2,4-dichlorophenoxyacetyl)-N'-(4-nitrophenyl)thiourea top

Crystal data top

C₁₅H₁₁Cl₂N₃O₄S	F(000) = 1632
M_r = 400.23	D_x = 1.573 Mg m⁻³
Monoclinic, C2/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -c2yc	Cell parameters from 25 reflections
a = 23.315 (5) Å	θ = 10–13°
b = 8.3190 (17) Å	µ = 0.53 mm⁻¹
c = 18.452 (4) Å	T = 293 K
β = 109.18 (3)°	Prism, yellow
V = 3380.2 (14) Å³	0.40 × 0.20 × 0.20 mm
Z = 8

Data collection top

Enraf–Nonius CAD-4 diffractometer	1943 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	R_int = 0.040
Graphite monochromator	θ_max = 26.0°, θ_min = 1.9°
ω/2θ scans	h = 0→28
Absorption correction: ψ scan (XCAD4; Harms & Wocadlo, 1995)	k = 0→10
T_min = 0.815, T_max = 0.901	l = −22→21
3400 measured reflections	3 standard reflections every 200 reflections
3316 independent reflections	intensity decay: none

Refinement top

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)] = 0.064	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.170	H-atom parameters constrained
S = 1.08	w = 1/[σ²(F_o²) + (0.065P)² + 3.2P] where P = (F_o² + 2F_c²)/3
3316 reflections	(Δ/σ)_max < 0.001
226 parameters	Δρ_max = 0.35 e Å⁻³
0 restraints	Δρ_min = −0.32 e Å⁻³

Special details top

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 (Å²) top

	x	y	z	U_iso*/U_eq
Cl1	0.30929 (7)	−0.16682 (16)	0.13860 (10)	0.0885 (5)
Cl2	0.50527 (5)	0.18519 (16)	0.14942 (7)	0.0669 (4)
S	0.63448 (6)	0.47539 (16)	0.03631 (7)	0.0687 (4)
O1	0.45816 (13)	0.1708 (4)	−0.01329 (17)	0.0625 (9)
O2	0.48267 (14)	0.3136 (4)	−0.17918 (18)	0.0686 (9)
O3	0.72048 (17)	0.8842 (5)	−0.2984 (2)	0.0862 (12)
O4	0.79429 (17)	0.8514 (5)	−0.1942 (2)	0.0872 (12)
N1	0.53525 (16)	0.3406 (4)	−0.05133 (19)	0.0509 (9)
H1A	0.5331	0.3140	−0.0073	0.061*
N2	0.58891 (15)	0.4661 (4)	−0.11901 (18)	0.0493 (9)
H2A	0.5602	0.4244	−0.1563	0.059*
N3	0.74164 (19)	0.8327 (5)	−0.2334 (2)	0.0626 (10)
C1	0.3522 (2)	−0.0664 (5)	0.0917 (3)	0.0572 (12)
C2	0.3332 (2)	−0.0604 (5)	0.0134 (3)	0.0616 (13)
H2B	0.2966	−0.1085	−0.0148	0.074*
C3	0.3675 (2)	0.0160 (5)	−0.0240 (3)	0.0573 (11)
H3A	0.3550	0.0157	−0.0773	0.069*
C4	0.42072 (19)	0.0937 (5)	0.0174 (2)	0.0485 (10)
C5	0.43892 (18)	0.0884 (5)	0.0971 (2)	0.0488 (10)
C6	0.4053 (2)	0.0077 (5)	0.1344 (3)	0.0554 (11)
H6A	0.4182	0.0033	0.1877	0.067*
C7	0.4400 (2)	0.1938 (6)	−0.0935 (2)	0.0570 (12)
H7A	0.4017	0.2513	−0.1110	0.068*
H7B	0.4345	0.0906	−0.1194	0.068*
C8	0.4884 (2)	0.2891 (5)	−0.1123 (3)	0.0517 (11)
C9	0.5865 (2)	0.4302 (5)	−0.0488 (2)	0.0512 (11)
C10	0.63035 (19)	0.5604 (5)	−0.1419 (2)	0.0460 (10)
C11	0.61426 (19)	0.5855 (5)	−0.2200 (2)	0.0536 (11)
H11A	0.5784	0.5412	−0.2525	0.064*
C12	0.65013 (19)	0.6741 (5)	−0.2502 (2)	0.0528 (11)
H12A	0.6390	0.6906	−0.3029	0.063*
C13	0.70294 (18)	0.7385 (5)	−0.2014 (2)	0.0445 (10)
C14	0.7206 (2)	0.7137 (5)	−0.1237 (2)	0.0550 (11)
H14A	0.7567	0.7572	−0.0915	0.066*
C15	0.68373 (19)	0.6229 (5)	−0.0938 (2)	0.0549 (11)
H15A	0.6952	0.6044	−0.0412	0.066*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Cl1	0.0996 (11)	0.0577 (8)	0.1329 (13)	−0.0050 (7)	0.0718 (10)	0.0091 (8)
Cl2	0.0645 (8)	0.0647 (8)	0.0635 (7)	−0.0077 (6)	0.0101 (6)	−0.0086 (6)
S	0.0937 (10)	0.0595 (8)	0.0492 (7)	−0.0119 (7)	0.0184 (6)	−0.0039 (6)
O1	0.0600 (19)	0.071 (2)	0.0527 (18)	−0.0097 (17)	0.0128 (15)	0.0117 (16)
O2	0.069 (2)	0.085 (2)	0.0494 (18)	0.0019 (18)	0.0161 (16)	0.0101 (18)
O3	0.095 (3)	0.098 (3)	0.064 (2)	−0.021 (2)	0.024 (2)	0.017 (2)
O4	0.071 (2)	0.110 (3)	0.077 (2)	−0.030 (2)	0.019 (2)	−0.005 (2)
N1	0.066 (2)	0.045 (2)	0.0410 (19)	0.0036 (19)	0.0164 (18)	0.0063 (16)
N2	0.059 (2)	0.044 (2)	0.0420 (19)	0.0008 (17)	0.0122 (17)	0.0015 (16)
N3	0.068 (3)	0.062 (3)	0.059 (3)	−0.008 (2)	0.023 (2)	−0.004 (2)
C1	0.060 (3)	0.034 (2)	0.086 (4)	0.009 (2)	0.035 (3)	0.010 (2)
C2	0.053 (3)	0.042 (3)	0.083 (4)	−0.002 (2)	0.013 (3)	−0.005 (2)
C3	0.058 (3)	0.052 (3)	0.057 (3)	−0.004 (2)	0.012 (2)	−0.002 (2)
C4	0.050 (3)	0.039 (2)	0.056 (3)	0.001 (2)	0.018 (2)	0.001 (2)
C5	0.052 (2)	0.036 (2)	0.056 (3)	0.005 (2)	0.016 (2)	−0.001 (2)
C6	0.068 (3)	0.045 (2)	0.060 (3)	0.011 (2)	0.030 (2)	0.008 (2)
C7	0.060 (3)	0.059 (3)	0.051 (3)	0.006 (2)	0.017 (2)	0.004 (2)
C8	0.062 (3)	0.045 (3)	0.048 (3)	0.013 (2)	0.017 (2)	0.002 (2)
C9	0.061 (3)	0.034 (2)	0.061 (3)	0.012 (2)	0.024 (2)	0.009 (2)
C10	0.050 (2)	0.037 (2)	0.049 (2)	0.011 (2)	0.014 (2)	0.0022 (19)
C11	0.057 (3)	0.049 (3)	0.046 (2)	−0.010 (2)	0.007 (2)	−0.008 (2)
C12	0.062 (3)	0.051 (3)	0.043 (2)	−0.001 (2)	0.014 (2)	−0.001 (2)
C13	0.052 (2)	0.035 (2)	0.048 (2)	0.0057 (19)	0.018 (2)	−0.0015 (19)
C14	0.050 (3)	0.058 (3)	0.052 (3)	−0.001 (2)	0.010 (2)	−0.006 (2)
C15	0.056 (3)	0.060 (3)	0.044 (2)	0.006 (2)	0.010 (2)	0.004 (2)

Geometric parameters (Å, º) top

Cl1—C1	1.738 (5)	C3—C4	1.385 (6)
Cl2—C5	1.730 (4)	C3—H3A	0.9300
S—C9	1.644 (5)	C4—C5	1.391 (6)
O1—C4	1.349 (5)	C5—C6	1.376 (6)
O1—C7	1.413 (5)	C6—H6A	0.9300
O2—C8	1.215 (5)	C7—C8	1.509 (6)
O3—N3	1.215 (5)	C7—H7A	0.9700
O4—N3	1.213 (5)	C7—H7B	0.9700
N1—C8	1.355 (5)	C10—C15	1.371 (6)
N1—C9	1.395 (5)	C10—C11	1.381 (5)
N1—H1A	0.8600	C11—C12	1.364 (6)
N2—C9	1.350 (5)	C11—H11A	0.9300
N2—C10	1.412 (5)	C12—C13	1.373 (6)
N2—H2A	0.8600	C12—H12A	0.9300
N3—C13	1.459 (5)	C13—C14	1.371 (6)
C1—C2	1.365 (6)	C14—C15	1.388 (6)
C1—C6	1.375 (6)	C14—H14A	0.9300
C2—C3	1.372 (6)	C15—H15A	0.9300
C2—H2B	0.9300

C4—O1—C7	119.5 (3)	O1—C7—H7A	109.9
C8—N1—C9	130.2 (4)	C8—C7—H7A	109.9
C8—N1—H1A	114.9	O1—C7—H7B	109.9
C9—N1—H1A	114.9	C8—C7—H7B	109.9
C9—N2—C10	131.2 (4)	H7A—C7—H7B	108.3
C9—N2—H2A	114.4	O2—C8—N1	125.4 (4)
C10—N2—H2A	114.4	O2—C8—C7	118.7 (4)
O4—N3—O3	123.2 (4)	N1—C8—C7	115.8 (4)
O4—N3—C13	117.8 (4)	N2—C9—N1	113.0 (4)
O3—N3—C13	119.0 (4)	N2—C9—S	129.5 (3)
C2—C1—C6	120.6 (4)	N1—C9—S	117.5 (3)
C2—C1—Cl1	120.3 (4)	C15—C10—C11	119.7 (4)
C6—C1—Cl1	119.1 (4)	C15—C10—N2	125.6 (4)
C1—C2—C3	120.5 (4)	C11—C10—N2	114.7 (4)
C1—C2—H2B	119.7	C12—C11—C10	121.0 (4)
C3—C2—H2B	119.7	C12—C11—H11A	119.5
C2—C3—C4	120.3 (4)	C10—C11—H11A	119.5
C2—C3—H3A	119.9	C11—C12—C13	118.7 (4)
C4—C3—H3A	119.9	C11—C12—H12A	120.6
O1—C4—C3	125.2 (4)	C13—C12—H12A	120.6
O1—C4—C5	116.4 (4)	C14—C13—C12	121.6 (4)
C3—C4—C5	118.3 (4)	C14—C13—N3	119.4 (4)
C6—C5—C4	121.2 (4)	C12—C13—N3	119.0 (4)
C6—C5—Cl2	120.0 (4)	C13—C14—C15	119.0 (4)
C4—C5—Cl2	118.8 (3)	C13—C14—H14A	120.5
C1—C6—C5	119.1 (4)	C15—C14—H14A	120.5
C1—C6—H6A	120.5	C10—C15—C14	119.9 (4)
C5—C6—H6A	120.5	C10—C15—H15A	120.1
O1—C7—C8	108.8 (4)	C14—C15—H15A	120.1

C6—C1—C2—C3	1.8 (7)	C10—N2—C9—N1	176.0 (4)
Cl1—C1—C2—C3	−178.7 (3)	C10—N2—C9—S	−4.5 (7)
C1—C2—C3—C4	−2.6 (7)	C8—N1—C9—N2	−1.5 (6)
C7—O1—C4—C3	8.1 (6)	C8—N1—C9—S	178.8 (3)
C7—O1—C4—C5	−174.2 (4)	C9—N2—C10—C15	8.6 (7)
C2—C3—C4—O1	179.2 (4)	C9—N2—C10—C11	−172.8 (4)
C2—C3—C4—C5	1.6 (7)	C15—C10—C11—C12	−1.2 (7)
O1—C4—C5—C6	−177.6 (4)	N2—C10—C11—C12	−179.9 (4)
C3—C4—C5—C6	0.3 (6)	C10—C11—C12—C13	0.0 (7)
O1—C4—C5—Cl2	2.3 (5)	C11—C12—C13—C14	1.0 (6)
C3—C4—C5—Cl2	−179.9 (3)	C11—C12—C13—N3	179.7 (4)
C2—C1—C6—C5	0.1 (6)	O4—N3—C13—C14	18.4 (6)
Cl1—C1—C6—C5	−179.4 (3)	O3—N3—C13—C14	−163.9 (4)
C4—C5—C6—C1	−1.1 (6)	O4—N3—C13—C12	−160.4 (4)
Cl2—C5—C6—C1	179.0 (3)	O3—N3—C13—C12	17.3 (6)
C4—O1—C7—C8	177.4 (4)	C12—C13—C14—C15	−0.8 (6)
C9—N1—C8—O2	0.0 (7)	N3—C13—C14—C15	−179.5 (4)
C9—N1—C8—C7	−180.0 (4)	C11—C10—C15—C14	1.4 (6)
O1—C7—C8—O2	175.9 (4)	N2—C10—C15—C14	179.9 (4)
O1—C7—C8—N1	−4.1 (5)	C13—C14—C15—C10	−0.4 (7)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1A···O1	0.86	2.09	2.559 (5)	114
N2—H2A···O2	0.86	1.95	2.678 (5)	142
C11—H11A···O2ⁱ	0.93	2.45	3.305 (5)	152
C15—H15A···S	0.93	2.56	3.225 (5)	129

Symmetry code: (i) −x+1, y, −z−1/2.

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N-(2,4-Dichloro­phenoxy­acet­yl)-N′-(4-nitro­phen­yl)thio­urea

Supporting information

Key indicators

checkCIF/PLATON results

N-(2,4-Dichlorophenoxyacetyl)-N′-(4-nitrophenyl)thiourea