N-(2-Chloro-4-nitro­phen­yl)-N′-octa­noylthio­urea

Yusof, M.S.M.; Ramlee, N.M.; Kadir, M.A.; Yamin, B.M.

doi:10.1107/S1600536807017266

N-(2-Chloro-4-nitrophenyl)-N′-octanoylthiourea

M. S. M. Yusof, N. M. Ramlee, M. A. Kadir and B. M. Yamin

The title compound, C₁₅H₂₀ClN₃O₃S, adopts a trans–cis configuration with respect to the positions of the octanoyl and 2-chloro-4-nitrophenyl groups relative to the S atom across their respective C—N bonds. Molecules exhibit intramolecular N—H

O hydrogen bonds and are linked into dimers through N—H

S interactions.

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Supporting information

	Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536807017266/bi2174sup1.cif Contains datablocks global, I
	Structure factor file (CIF format) https://doi.org/10.1107/S1600536807017266/bi2174Isup2.hkl Contains datablock I

CCDC reference: 646733

checkCIF report

Key indicators

Single-crystal X-ray study
T = 298 K
Mean (C-C) = 0.005 Å
R factor = 0.050
wR factor = 0.128
Data-to-parameter ratio = 14.9

checkCIF/PLATON results

No syntax errors found



Alert level B
PLAT027_ALERT_3_B _diffrn_reflns_theta_full (too) Low ............      24.99 Deg.

Alert level C
PLAT152_ALERT_1_C Supplied and Calc Volume s.u. Inconsistent .....          ?
PLAT340_ALERT_3_C Low Bond Precision on C-C bonds (x 1000) Ang ...          5
PLAT360_ALERT_2_C Short  C(sp3)-C(sp3) Bond  C2     -   C3     ...       1.43 Ang.
PLAT431_ALERT_2_C Short Inter HL..A Contact  Cl1    ..  O2      ..       3.21 Ang.

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

   1 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
   2 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
   0 ALERT type 4 Improvement, methodology, query or suggestion
   0 ALERT type 5 Informative message, check

Computing details top

Data collection: SMART (Bruker, 2000); cell refinement: SAINT (Bruker, 2000); data reduction: SAINT; 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, PARST (Nardelli, 1995) and PLATON (Spek, 2003).

N-(2-Chloro-4-nitrophenyl)-N'-octanoylthiourea top

Crystal data top

C₁₅H₂₀ClN₃O₃S	F(000) = 752
M_r = 357.85	D_x = 1.345 Mg m⁻³
Monoclinic, P2₁/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 769 reflections
a = 12.737 (4) Å	θ = 1.7–25.0°
b = 9.355 (3) Å	µ = 0.35 mm⁻¹
c = 15.992 (5) Å	T = 298 K
β = 111.960 (5)°	Block, light yellow
V = 1767.3 (9) Å³	0.35 × 0.25 × 0.24 mm
Z = 4

Data collection top

Bruker SMART APEX CCD diffractometer	3105 independent reflections
Radiation source: fine-focus sealed tube	2311 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.027
ω scans	θ_max = 25.0°, θ_min = 1.7°
Absorption correction: multi-scan (SADABS; Bruker, 2000)	h = −15→15
T_min = 0.887, T_max = 0.921	k = −10→11
8878 measured reflections	l = −19→11

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)] = 0.050	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.128	H-atom parameters constrained
S = 1.03	w = 1/[σ²(F_o²) + (0.0574P)² + 0.734P] where P = (F_o² + 2F_c²)/3
3105 reflections	(Δ/σ)_max < 0.001
209 parameters	Δρ_max = 0.25 e Å⁻³
0 restraints	Δρ_min = −0.18 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	0.03292 (6)	0.82372 (8)	0.47124 (5)	0.0695 (3)
S1	0.41157 (6)	0.50745 (11)	0.59437 (5)	0.0761 (3)
O1	0.17878 (18)	0.7184 (3)	0.33722 (14)	0.0809 (7)
O2	0.0189 (2)	0.4862 (3)	0.80031 (15)	0.0818 (7)
O3	−0.1008 (2)	0.6423 (3)	0.72201 (17)	0.0920 (8)
N1	0.33867 (18)	0.6066 (3)	0.42887 (15)	0.0590 (6)
H1D	0.4047	0.5801	0.4321	0.071*
N2	0.20585 (17)	0.6070 (2)	0.49345 (14)	0.0522 (5)
H2A	0.1648	0.6427	0.4421	0.063*
N3	−0.0185 (2)	0.5660 (3)	0.73610 (19)	0.0641 (6)
C1	0.3621 (4)	0.3423 (5)	−0.1337 (3)	0.1170 (15)
H1A	0.3627	0.4377	−0.1556	0.176*
H1B	0.3200	0.2810	−0.1830	0.176*
H1C	0.4384	0.3079	−0.1063	0.176*
C2	0.3079 (4)	0.3429 (5)	−0.0655 (3)	0.1158 (14)
H2B	0.2284	0.3659	−0.0961	0.139*
H2C	0.3123	0.2469	−0.0414	0.139*
C3	0.3555 (3)	0.4399 (5)	0.0085 (3)	0.1019 (13)
H3A	0.3470	0.5363	−0.0156	0.122*
H3B	0.4360	0.4207	0.0365	0.122*
C4	0.3061 (3)	0.4361 (4)	0.0817 (2)	0.0904 (11)
H4A	0.2242	0.4382	0.0533	0.108*
H4B	0.3273	0.3465	0.1142	0.108*
C5	0.3438 (3)	0.5564 (4)	0.1477 (2)	0.0765 (9)
H5A	0.3245	0.6460	0.1149	0.092*
H5B	0.4255	0.5528	0.1771	0.092*
C6	0.2933 (3)	0.5560 (4)	0.2187 (2)	0.0752 (9)
H6A	0.3174	0.4700	0.2548	0.090*
H6B	0.2115	0.5528	0.1896	0.090*
C7	0.3265 (3)	0.6858 (3)	0.2809 (2)	0.0681 (8)
H7A	0.4082	0.6903	0.3105	0.082*
H7B	0.3009	0.7724	0.2458	0.082*
C8	0.2737 (3)	0.6751 (3)	0.3503 (2)	0.0623 (7)
C9	0.3125 (2)	0.5743 (3)	0.50373 (18)	0.0529 (7)
C10	0.1519 (2)	0.5907 (3)	0.55526 (17)	0.0476 (6)
C11	0.1734 (2)	0.4797 (3)	0.61655 (19)	0.0596 (7)
H11	0.2266	0.4105	0.6183	0.072*
C12	0.1167 (2)	0.4704 (3)	0.67537 (19)	0.0582 (7)
H12	0.1320	0.3962	0.7169	0.070*
C13	0.0382 (2)	0.5720 (3)	0.67117 (17)	0.0506 (6)
C14	0.0110 (2)	0.6800 (3)	0.60930 (19)	0.0540 (7)
H14	−0.0445	0.7463	0.6066	0.065*
C15	0.0676 (2)	0.6890 (3)	0.55083 (17)	0.0478 (6)

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Cl1	0.0729 (5)	0.0646 (5)	0.0807 (5)	0.0196 (4)	0.0399 (4)	0.0172 (4)
S1	0.0527 (4)	0.1179 (7)	0.0587 (5)	0.0203 (4)	0.0218 (4)	0.0162 (5)
O1	0.0697 (14)	0.1125 (18)	0.0669 (13)	0.0387 (13)	0.0330 (11)	0.0272 (12)
O2	0.0980 (17)	0.0887 (16)	0.0730 (15)	0.0034 (13)	0.0486 (14)	0.0122 (13)
O3	0.0889 (17)	0.0973 (17)	0.118 (2)	0.0210 (14)	0.0719 (16)	0.0166 (15)
N1	0.0484 (13)	0.0774 (16)	0.0566 (14)	0.0162 (11)	0.0257 (11)	0.0070 (12)
N2	0.0471 (12)	0.0634 (14)	0.0482 (12)	0.0107 (10)	0.0201 (10)	0.0025 (11)
N3	0.0675 (16)	0.0647 (15)	0.0722 (17)	−0.0070 (13)	0.0401 (14)	−0.0070 (14)
C1	0.092 (3)	0.163 (4)	0.096 (3)	−0.007 (3)	0.036 (2)	−0.035 (3)
C2	0.111 (3)	0.128 (4)	0.108 (3)	−0.012 (3)	0.041 (3)	−0.018 (3)
C3	0.092 (3)	0.121 (3)	0.105 (3)	−0.021 (2)	0.050 (2)	−0.033 (3)
C4	0.087 (2)	0.098 (3)	0.094 (3)	−0.002 (2)	0.043 (2)	−0.011 (2)
C5	0.078 (2)	0.086 (2)	0.079 (2)	0.0042 (18)	0.0451 (19)	0.0063 (19)
C6	0.073 (2)	0.091 (2)	0.074 (2)	0.0031 (17)	0.0409 (18)	0.0102 (19)
C7	0.0673 (19)	0.078 (2)	0.0688 (19)	0.0157 (16)	0.0366 (16)	0.0189 (17)
C8	0.0614 (18)	0.0702 (19)	0.0588 (18)	0.0118 (15)	0.0263 (15)	0.0077 (15)
C9	0.0518 (15)	0.0573 (16)	0.0517 (16)	0.0039 (12)	0.0219 (13)	−0.0041 (13)
C10	0.0444 (13)	0.0509 (15)	0.0483 (15)	−0.0005 (12)	0.0182 (12)	−0.0065 (12)
C11	0.0580 (17)	0.0585 (17)	0.0678 (18)	0.0115 (13)	0.0298 (15)	0.0036 (15)
C12	0.0618 (17)	0.0582 (17)	0.0560 (16)	0.0019 (14)	0.0234 (14)	0.0036 (14)
C13	0.0486 (14)	0.0545 (16)	0.0540 (16)	−0.0041 (12)	0.0254 (13)	−0.0063 (13)
C14	0.0484 (15)	0.0519 (16)	0.0653 (17)	0.0031 (12)	0.0253 (14)	−0.0066 (14)
C15	0.0439 (13)	0.0473 (14)	0.0516 (15)	−0.0009 (11)	0.0171 (12)	−0.0051 (12)

Geometric parameters (Å, º) top

Cl1—C15	1.727 (3)	C4—C5	1.494 (5)
S1—C9	1.648 (3)	C4—H4A	0.970
O1—C8	1.217 (3)	C4—H4B	0.970
O2—N3	1.214 (3)	C5—C6	1.500 (4)
O3—N3	1.218 (3)	C5—H5A	0.970
N1—C8	1.377 (4)	C5—H5B	0.970
N1—C9	1.391 (3)	C6—C7	1.525 (4)
N1—H1D	0.860	C6—H6A	0.970
N2—C9	1.341 (3)	C6—H6B	0.970
N2—C10	1.407 (3)	C7—C8	1.501 (4)
N2—H2A	0.860	C7—H7A	0.970
N3—C13	1.470 (3)	C7—H7B	0.970
C1—C2	1.492 (6)	C10—C11	1.383 (4)
C1—H1A	0.960	C10—C15	1.395 (3)
C1—H1B	0.960	C11—C12	1.386 (4)
C1—H1C	0.960	C11—H11	0.930
C2—C3	1.434 (5)	C12—C13	1.364 (4)
C2—H2B	0.970	C12—H12	0.930
C2—H2C	0.970	C13—C14	1.365 (4)
C3—C4	1.523 (5)	C14—C15	1.380 (3)
C3—H3A	0.970	C14—H14	0.930
C3—H3B	0.970

C8—N1—C9	129.1 (2)	H5A—C5—H5B	107.6
C8—N1—H1D	115.4	C5—C6—C7	113.5 (3)
C9—N1—H1D	115.4	C5—C6—H6A	108.9
C9—N2—C10	128.9 (2)	C7—C6—H6A	108.9
C9—N2—H2A	115.6	C5—C6—H6B	108.9
C10—N2—H2A	115.6	C7—C6—H6B	108.9
O2—N3—O3	123.7 (3)	H6A—C6—H6B	107.7
O2—N3—C13	118.7 (3)	C8—C7—C6	109.7 (3)
O3—N3—C13	117.6 (3)	C8—C7—H7A	109.7
C2—C1—H1A	109.5	C6—C7—H7A	109.7
C2—C1—H1B	109.5	C8—C7—H7B	109.7
H1A—C1—H1B	109.5	C6—C7—H7B	109.7
C2—C1—H1C	109.5	H7A—C7—H7B	108.2
H1A—C1—H1C	109.5	O1—C8—N1	122.1 (3)
H1B—C1—H1C	109.5	O1—C8—C7	122.7 (3)
C3—C2—C1	115.9 (4)	N1—C8—C7	115.1 (2)
C3—C2—H2B	108.3	N2—C9—N1	113.8 (2)
C1—C2—H2B	108.3	N2—C9—S1	127.0 (2)
C3—C2—H2C	108.3	N1—C9—S1	119.23 (19)
C1—C2—H2C	108.3	C11—C10—C15	118.4 (2)
H2B—C2—H2C	107.4	C11—C10—N2	124.0 (2)
C2—C3—C4	116.8 (4)	C15—C10—N2	117.5 (2)
C2—C3—H3A	108.1	C10—C11—C12	120.9 (3)
C4—C3—H3A	108.1	C10—C11—H11	119.6
C2—C3—H3B	108.1	C12—C11—H11	119.6
C4—C3—H3B	108.1	C13—C12—C11	118.8 (3)
H3A—C3—H3B	107.3	C13—C12—H12	120.6
C5—C4—C3	114.2 (3)	C11—C12—H12	120.6
C5—C4—H4A	108.7	C12—C13—C14	122.3 (2)
C3—C4—H4A	108.7	C12—C13—N3	118.9 (3)
C5—C4—H4B	108.7	C14—C13—N3	118.8 (2)
C3—C4—H4B	108.7	C13—C14—C15	118.8 (2)
H4A—C4—H4B	107.6	C13—C14—H14	120.6
C4—C5—C6	114.7 (3)	C15—C14—H14	120.6
C4—C5—H5A	108.6	C14—C15—C10	120.8 (2)
C6—C5—H5A	108.6	C14—C15—Cl1	119.3 (2)
C4—C5—H5B	108.6	C10—C15—Cl1	119.9 (2)
C6—C5—H5B	108.6

C1—C2—C3—C4	−176.5 (4)	N2—C10—C11—C12	−179.9 (2)
C2—C3—C4—C5	−169.4 (4)	C10—C11—C12—C13	0.7 (4)
C3—C4—C5—C6	178.5 (3)	C11—C12—C13—C14	2.0 (4)
C4—C5—C6—C7	−175.8 (3)	C11—C12—C13—N3	−177.3 (2)
C5—C6—C7—C8	−179.2 (3)	O2—N3—C13—C12	11.9 (4)
C9—N1—C8—O1	0.2 (5)	O3—N3—C13—C12	−168.1 (3)
C9—N1—C8—C7	−177.0 (3)	O2—N3—C13—C14	−167.4 (3)
C6—C7—C8—O1	−86.8 (4)	O3—N3—C13—C14	12.6 (4)
C6—C7—C8—N1	90.4 (3)	C12—C13—C14—C15	−2.0 (4)
C10—N2—C9—N1	−179.0 (2)	N3—C13—C14—C15	177.3 (2)
C10—N2—C9—S1	−1.2 (4)	C13—C14—C15—C10	−0.7 (4)
C8—N1—C9—N2	5.0 (4)	C13—C14—C15—Cl1	179.2 (2)
C8—N1—C9—S1	−173.0 (2)	C11—C10—C15—C14	3.3 (4)
C9—N2—C10—C11	−34.4 (4)	N2—C10—C15—C14	−179.9 (2)
C9—N2—C10—C15	148.9 (3)	C11—C10—C15—Cl1	−176.6 (2)
C15—C10—C11—C12	−3.3 (4)	N2—C10—C15—Cl1	0.2 (3)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N2—H2A···O1	0.86	1.89	2.608 (3)	140
N1—H1D···S1ⁱ	0.86	2.66	3.504 (3)	168

Symmetry code: (i) −x+1, −y+1, −z+1.

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N-(2-Chloro-4-nitro­phen­yl)-N′-octa­noylthio­urea

Supporting information

Key indicators

checkCIF/PLATON results

N-(2-Chloro-4-nitrophenyl)-N′-octanoylthiourea