N-[(2,4-Dimethyl­phen­yl)carbamothio­yl]-2-methyl­benzamide

Yamin, B.M.; Yousuf, S.; Yusof, M.S.M.; Jusoh, R.H.

doi:10.1107/S1600536808009501

organic compounds

CRYSTALLOGRAPHIC
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ISSN: 2056-9890

Volume 64| Part 5| May 2008| Page o832

doi:10.1107/S1600536808009501

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N-[(2,4-Dimethylphenyl)carbamothioyl]-2-methylbenzamide

B. M. Yamin,^a S. Yousuf,^b ^* M. S. M. Yusof ^c and R. H. Jusoh ^c

^aSchool of Chemical Sciences and Food Technology, Universiti Kebangsaan Malaysia, UKM 43650 Bangi Selangor, Malaysia, ^bHEJ Research Institute of Chemistry, International Center for Chemical and Biological Sciences, University of Karachi, Karachi 75270, Pakistan, and ^cDepartment of Chemistry, Universiti Malaysia Terengganu, Manngabang Telipot, Terengganu, Malaysia
^*Correspondence e-mail: sammer_yousuf@yahoo.com

(Received 4 April 2008; accepted 7 April 2008; online 10 April 2008)

The title compound, C₁₇H₁₈N₂OS, adopts a trans–cis geometry of the thiourea group which is stabilized by intramolecular hydrogen bonds between the O atom of the carbonyl group and the H atom of the thioamide group. A C—H⋯S intramolecular hydrogen bond is also present. In the crystal structure, molecules are linked by intermolecular N—H⋯S hydrogen bonds to form centrosymmetric dimers.

Related literature

For the crystal structure of 1-(2,3-dimethylphenyl)-3-(2-methylbenzoyl)thiourea, which is isomeric with the title compound, see: Khawar Rauf et al. (2007 ). For bond-length data, see: Allen et al. (1987 ).

Experimental

Crystal data

C₁₇H₁₈N₂OS
M_r = 298.39
Triclinic, $[P \overline 1]$
a = 6.2569 (15) Å
b = 9.862 (2) Å
c = 13.986 (3) Å
α = 69.461 (4)°
β = 86.199 (4)°
γ = 75.206 (4)°
V = 781.1 (3) Å³
Z = 2
Mo Kα radiation
μ = 0.21 mm⁻¹
T = 298 (2) K
0.27 × 0.18 × 0.09 mm

Data collection

Bruker SMART APEX CCD area-detector diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2000 ) T_min = 0.946, T_max = 0.982
7817 measured reflections
2904 independent reflections
2069 reflections with I > 2σ(I)
R_int = 0.034

Refinement

R[F² > 2σ(F²)] = 0.047
wR(F²) = 0.119
S = 1.02
2904 reflections
193 parameters
H-atom parameters constrained
Δρ_max = 0.23 e Å⁻³
Δρ_min = −0.17 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N2—H2⋯O1	0.86	2.03	2.706	135
C17—H17B⋯S1	0.96	2.80	3.496	130
N1—H1⋯S1ⁱ	0.86	2.57	3.372	155
Symmetry code: (i) -x, -y+1, -z+1.

Data collection: SMART (Bruker, 2000); cell refinement: SAINT (Bruker, 2000); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXTL, PARST (Nardelli, 1995 ) and PLATON (Spek, 2003 ).

Supporting information

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536808009501/at2557sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536808009501/at2557Isup2.hkl

checkCIF report

Comment top

The title compound, (I), is isomeric to the previously reported 1-(2,3-dimethylphenyl)-3-(2-methylbenzoyl)thiourea (II), (Khawar Rauf et al., 2007) with the difference that the 2,3-dimethylphenyl ring is replaced by 2,4-dimethylphenyl (Fig.1). The bond lengths and angles are in normal range (Allen et al., 1987) and in agreement with those in (II). The central thiourea moiety (S1/N1/N2/C9), 2-methylbenzoyl (C1—C8), and 2,3-dimethylphenyl (C10—C15) rings are each planar with a maximum deviation of 0.040 (2)Å for C8 atom from the least square plane. The dihedral angles between the thiourea moiety and the 2-methylbenzoyl and 2,3-dimethylphenyl rings are 52.96 (11) and 70.34 (12)°, respectively. The trans-cis geometry of the thiourea moiety is stabilized by N2—H2···O1 and C17—H17B···S1 intramolecular hydrogen bonds. In the crystal structure, the molecules are linked to form dimers by the N1—H1···S1 intermolecular hydrogen bond (symmtery codes as in Table 2) and arranged parallel to c axis (Fig.2).

Related literature top

For the crystal structure of 1-(2,3-dimethylphenyl)-3-(2-methylbenzoyl)thiourea which is isomeric to the title compound, see: Khawar Rauf et al. (2007). For bond-length data, see: Allen et al. (1987).

Experimental top

The mixture of 2-methylbenzoyl chloride (9.720 g, 0.025 mol) with the equimolar amount of ammonium thiocyanate (1.903 g, 0.025 mol) and 2,3-dimethyl aniline (3.025 g, 0.025 mol) in 40 ml dry acetone was refluxed with stirring for 4 h. The solution was filtered and left to evaporate at room temperature. The colourless crystals obtained after a few days, was found suitable for X-ray investigations. The yield was 85% with melting point 413.2–415.7 K.

Computing details top

Data collection: SMART (Bruker, 2000); cell refinement: SAINT (Bruker, 2000); data reduction: SAINT (Bruker, 2000); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXTL (Sheldrick, 2008), PARST (Nardelli, 1995) and PLATON (Spek, 2003).

Figures top

	Fig. 1. The molecular sStructure of (I) with displacement ellipsoids drawn at 50% probability level. The dashed lines indicates the intramolecular hydrogen bonds.
	Fig. 2. A packing diagram of (I). Hydrogen bonds are shown by dashed lines.

N-[(2,4-Dimethylphenyl)carbamothioyl]-2-methylbenzamide top

Crystal data top

C₁₇H₁₈N₂OS	Z = 2
M_r = 298.39	F(000) = 316
Triclinic, P1	D_x = 1.269 Mg m⁻³
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 6.2569 (15) Å	Cell parameters from 1377 reflections
b = 9.862 (2) Å	θ = 1.5–25.5°
c = 13.986 (3) Å	µ = 0.21 mm⁻¹
α = 69.461 (4)°	T = 298 K
β = 86.199 (4)°	Slab, colourless
γ = 75.206 (4)°	0.27 × 0.18 × 0.09 mm
V = 781.1 (3) Å³

Data collection top

Bruker SMART APEX CCD area-detector diffractometer	2904 independent reflections
Radiation source: fine-focus sealed tube	2069 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.034
Detector resolution: 83.66 pixels mm^-1	θ_max = 25.5°, θ_min = 1.5°
ω scans	h = −7→7
Absorption correction: multi-scan (SADABS; Bruker, 2000)	k = −11→11
T_min = 0.946, T_max = 0.982	l = −16→16
7817 measured reflections

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)] = 0.047	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.119	H-atom parameters constrained
S = 1.02	w = 1/[σ²(F_o²) + (0.0567P)² + 0.1084P] where P = (F_o² + 2F_c²)/3
2904 reflections	(Δ/σ)_max = 0.001
193 parameters	Δρ_max = 0.23 e Å⁻³
0 restraints	Δρ_min = −0.17 e Å⁻³

Crystal data top

C₁₇H₁₈N₂OS	γ = 75.206 (4)°
M_r = 298.39	V = 781.1 (3) Å³
Triclinic, P1	Z = 2
a = 6.2569 (15) Å	Mo Kα radiation
b = 9.862 (2) Å	µ = 0.21 mm⁻¹
c = 13.986 (3) Å	T = 298 K
α = 69.461 (4)°	0.27 × 0.18 × 0.09 mm
β = 86.199 (4)°

Data collection top

Bruker SMART APEX CCD area-detector diffractometer	2904 independent reflections
Absorption correction: multi-scan (SADABS; Bruker, 2000)	2069 reflections with I > 2σ(I)
T_min = 0.946, T_max = 0.982	R_int = 0.034
7817 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.047	0 restraints
wR(F²) = 0.119	H-atom parameters constrained
S = 1.02	Δρ_max = 0.23 e Å⁻³
2904 reflections	Δρ_min = −0.17 e Å⁻³
193 parameters

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
S1	0.00124 (10)	0.51524 (6)	0.34145 (4)	0.0441 (2)
O1	0.2196 (3)	0.02671 (18)	0.54848 (13)	0.0630 (5)
N1	0.1412 (3)	0.27939 (19)	0.50519 (13)	0.0374 (4)
H1	0.1341	0.3473	0.5313	0.045*
N2	0.0595 (3)	0.22917 (19)	0.36460 (13)	0.0394 (5)
H2	0.0883	0.1375	0.4048	0.047*
C1	0.2131 (4)	0.0521 (3)	0.75752 (18)	0.0519 (6)
H1A	0.1042	0.0051	0.7537	0.062*
C2	0.2787 (5)	0.0473 (3)	0.85127 (19)	0.0644 (8)
H2A	0.2120	−0.0007	0.9105	0.077*
C3	0.4424 (5)	0.1138 (3)	0.8562 (2)	0.0639 (8)
H3	0.4864	0.1112	0.9192	0.077*
C4	0.5414 (4)	0.1835 (3)	0.77013 (19)	0.0541 (7)
H4	0.6543	0.2264	0.7754	0.065*
C5	0.4783 (4)	0.1923 (3)	0.67457 (17)	0.0430 (6)
C6	0.3089 (3)	0.1265 (2)	0.66943 (16)	0.0367 (5)
C7	0.5968 (5)	0.2679 (4)	0.5822 (2)	0.0696 (8)
H7A	0.5020	0.3625	0.5433	0.104*
H7B	0.6355	0.2060	0.5407	0.104*
H7C	0.7286	0.2835	0.6034	0.104*
C8	0.2225 (4)	0.1361 (2)	0.56942 (17)	0.0393 (5)
C9	0.0679 (3)	0.3321 (2)	0.40383 (15)	0.0334 (5)
C10	0.0056 (4)	0.2603 (2)	0.25979 (16)	0.0366 (5)
C11	0.1738 (4)	0.2193 (3)	0.19879 (18)	0.0473 (6)
H11	0.3167	0.1740	0.2259	0.057*
C12	0.1297 (4)	0.2456 (3)	0.09727 (19)	0.0538 (7)
H12	0.2440	0.2181	0.0565	0.065*
C13	−0.0810 (4)	0.3119 (3)	0.05573 (17)	0.0499 (6)
C14	−0.2460 (4)	0.3481 (3)	0.11976 (17)	0.0463 (6)
H14	−0.3895	0.3910	0.0929	0.056*
C15	−0.2098 (4)	0.3239 (2)	0.22153 (16)	0.0394 (5)
C16	−0.1300 (5)	0.3419 (3)	−0.05520 (19)	0.0748 (9)
H16A	−0.0953	0.4338	−0.0968	0.112*
H16B	−0.2839	0.3494	−0.0643	0.112*
H16C	−0.0420	0.2614	−0.0750	0.112*
C17	−0.3997 (4)	0.3598 (3)	0.28774 (19)	0.0564 (7)
H17A	−0.5362	0.3917	0.2493	0.085*
H17B	−0.3828	0.4383	0.3099	0.085*
H17C	−0.4015	0.2723	0.3462	0.085*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
S1	0.0630 (4)	0.0333 (3)	0.0343 (3)	−0.0086 (3)	−0.0061 (3)	−0.0108 (2)
O1	0.1010 (14)	0.0356 (9)	0.0529 (11)	−0.0138 (9)	−0.0262 (10)	−0.0130 (8)
N1	0.0502 (11)	0.0303 (9)	0.0333 (10)	−0.0070 (8)	−0.0101 (8)	−0.0128 (8)
N2	0.0524 (12)	0.0300 (9)	0.0347 (10)	−0.0063 (8)	−0.0104 (8)	−0.0107 (8)
C1	0.0657 (16)	0.0445 (14)	0.0448 (15)	−0.0180 (12)	−0.0029 (12)	−0.0108 (12)
C2	0.092 (2)	0.0591 (17)	0.0327 (14)	−0.0153 (16)	0.0040 (14)	−0.0072 (13)
C3	0.089 (2)	0.0587 (17)	0.0398 (16)	−0.0019 (16)	−0.0202 (15)	−0.0193 (13)
C4	0.0576 (16)	0.0573 (16)	0.0483 (16)	−0.0066 (13)	−0.0184 (13)	−0.0214 (13)
C5	0.0421 (13)	0.0453 (14)	0.0402 (14)	−0.0053 (11)	−0.0066 (11)	−0.0157 (11)
C6	0.0424 (13)	0.0311 (11)	0.0339 (12)	−0.0037 (10)	−0.0052 (10)	−0.0109 (10)
C7	0.0598 (17)	0.101 (2)	0.0598 (18)	−0.0409 (16)	0.0074 (14)	−0.0278 (17)
C8	0.0450 (13)	0.0363 (12)	0.0380 (13)	−0.0111 (10)	−0.0058 (10)	−0.0127 (10)
C9	0.0319 (11)	0.0387 (12)	0.0313 (12)	−0.0077 (9)	−0.0019 (9)	−0.0144 (10)
C10	0.0494 (14)	0.0326 (11)	0.0315 (12)	−0.0110 (10)	−0.0056 (10)	−0.0135 (9)
C11	0.0478 (14)	0.0472 (14)	0.0487 (15)	−0.0026 (11)	−0.0052 (12)	−0.0239 (12)
C12	0.0579 (17)	0.0569 (16)	0.0475 (15)	−0.0036 (13)	0.0052 (13)	−0.0274 (13)
C13	0.0694 (17)	0.0452 (14)	0.0338 (13)	−0.0083 (12)	−0.0056 (12)	−0.0152 (11)
C14	0.0504 (14)	0.0455 (14)	0.0404 (14)	−0.0049 (11)	−0.0128 (11)	−0.0143 (11)
C15	0.0428 (13)	0.0400 (12)	0.0361 (13)	−0.0090 (10)	−0.0031 (10)	−0.0141 (10)
C16	0.101 (2)	0.080 (2)	0.0370 (15)	−0.0053 (17)	−0.0084 (15)	−0.0226 (14)
C17	0.0470 (15)	0.0767 (19)	0.0493 (16)	−0.0126 (13)	−0.0008 (12)	−0.0279 (14)

Geometric parameters (Å, º) top

S1—C9	1.660 (2)	C7—H7A	0.9600
O1—C8	1.218 (3)	C7—H7B	0.9600
N1—C8	1.366 (3)	C7—H7C	0.9600
N1—C9	1.392 (3)	C10—C11	1.380 (3)
N1—H1	0.8600	C10—C15	1.387 (3)
N2—C9	1.325 (3)	C11—C12	1.384 (3)
N2—C10	1.433 (3)	C11—H11	0.9300
N2—H2	0.8600	C12—C13	1.378 (3)
C1—C6	1.381 (3)	C12—H12	0.9300
C1—C2	1.381 (3)	C13—C14	1.381 (3)
C1—H1A	0.9300	C13—C16	1.511 (3)
C2—C3	1.367 (4)	C14—C15	1.383 (3)
C2—H2A	0.9300	C14—H14	0.9300
C3—C4	1.358 (4)	C15—C17	1.505 (3)
C3—H3	0.9300	C16—H16A	0.9600
C4—C5	1.386 (3)	C16—H16B	0.9600
C4—H4	0.9300	C16—H16C	0.9600
C5—C6	1.395 (3)	C17—H17A	0.9600
C5—C7	1.501 (3)	C17—H17B	0.9600
C6—C8	1.496 (3)	C17—H17C	0.9600

C8—N1—C9	129.81 (17)	N2—C9—N1	116.13 (18)
C8—N1—H1	115.1	N2—C9—S1	125.20 (16)
C9—N1—H1	115.1	N1—C9—S1	118.67 (15)
C9—N2—C10	124.43 (18)	C11—C10—C15	120.8 (2)
C9—N2—H2	117.8	C11—C10—N2	117.8 (2)
C10—N2—H2	117.8	C15—C10—N2	121.3 (2)
C6—C1—C2	120.2 (2)	C10—C11—C12	120.0 (2)
C6—C1—H1A	119.9	C10—C11—H11	120.0
C2—C1—H1A	119.9	C12—C11—H11	120.0
C3—C2—C1	119.4 (2)	C13—C12—C11	121.0 (2)
C3—C2—H2A	120.3	C13—C12—H12	119.5
C1—C2—H2A	120.3	C11—C12—H12	119.5
C4—C3—C2	120.7 (2)	C12—C13—C14	117.4 (2)
C4—C3—H3	119.7	C12—C13—C16	121.2 (2)
C2—C3—H3	119.7	C14—C13—C16	121.4 (2)
C3—C4—C5	121.6 (2)	C13—C14—C15	123.6 (2)
C3—C4—H4	119.2	C13—C14—H14	118.2
C5—C4—H4	119.2	C15—C14—H14	118.2
C4—C5—C6	117.7 (2)	C14—C15—C10	117.2 (2)
C4—C5—C7	119.4 (2)	C14—C15—C17	120.6 (2)
C6—C5—C7	122.9 (2)	C10—C15—C17	122.2 (2)
C1—C6—C5	120.4 (2)	C13—C16—H16A	109.5
C1—C6—C8	118.0 (2)	C13—C16—H16B	109.5
C5—C6—C8	121.57 (19)	H16A—C16—H16B	109.5
C5—C7—H7A	109.5	C13—C16—H16C	109.5
C5—C7—H7B	109.5	H16A—C16—H16C	109.5
H7A—C7—H7B	109.5	H16B—C16—H16C	109.5
C5—C7—H7C	109.5	C15—C17—H17A	109.5
H7A—C7—H7C	109.5	C15—C17—H17B	109.5
H7B—C7—H7C	109.5	H17A—C17—H17B	109.5
O1—C8—N1	123.27 (19)	C15—C17—H17C	109.5
O1—C8—C6	123.18 (19)	H17A—C17—H17C	109.5
N1—C8—C6	113.52 (18)	H17B—C17—H17C	109.5

C6—C1—C2—C3	−1.5 (4)	C10—N2—C9—S1	4.5 (3)
C1—C2—C3—C4	−0.3 (4)	C8—N1—C9—N2	5.5 (3)
C2—C3—C4—C5	1.2 (4)	C8—N1—C9—S1	−173.80 (17)
C3—C4—C5—C6	−0.2 (3)	C9—N2—C10—C11	108.4 (2)
C3—C4—C5—C7	−178.7 (3)	C9—N2—C10—C15	−74.2 (3)
C2—C1—C6—C5	2.5 (3)	C15—C10—C11—C12	1.9 (3)
C2—C1—C6—C8	−176.4 (2)	N2—C10—C11—C12	179.4 (2)
C4—C5—C6—C1	−1.7 (3)	C10—C11—C12—C13	−0.3 (4)
C7—C5—C6—C1	176.8 (2)	C11—C12—C13—C14	−1.3 (4)
C4—C5—C6—C8	177.2 (2)	C11—C12—C13—C16	179.6 (2)
C7—C5—C6—C8	−4.3 (3)	C12—C13—C14—C15	1.3 (4)
C9—N1—C8—O1	−8.8 (4)	C16—C13—C14—C15	−179.6 (2)
C9—N1—C8—C6	173.14 (19)	C13—C14—C15—C10	0.3 (3)
C1—C6—C8—O1	−57.8 (3)	C13—C14—C15—C17	−177.2 (2)
C5—C6—C8—O1	123.3 (3)	C11—C10—C15—C14	−1.9 (3)
C1—C6—C8—N1	120.3 (2)	N2—C10—C15—C14	−179.21 (19)
C5—C6—C8—N1	−58.6 (3)	C11—C10—C15—C17	175.5 (2)
C10—N2—C9—N1	−174.81 (18)	N2—C10—C15—C17	−1.8 (3)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N2—H2···O1	0.86	2.03	2.706	135
C17—H17B···S1	0.96	2.80	3.496	130
N1—H1···S1ⁱ	0.86	2.57	3.372	155

Symmetry code: (i) −x, −y+1, −z+1.

Experimental details

Crystal data
Chemical formula	C₁₇H₁₈N₂OS
M_r	298.39
Crystal system, space group	Triclinic, P1
Temperature (K)	298
a, b, c (Å)	6.2569 (15), 9.862 (2), 13.986 (3)
α, β, γ (°)	69.461 (4), 86.199 (4), 75.206 (4)
V (Å³)	781.1 (3)
Z	2
Radiation type	Mo Kα
µ (mm⁻¹)	0.21
Crystal size (mm)	0.27 × 0.18 × 0.09

Data collection
Diffractometer	Bruker SMART APEX CCD area-detector diffractometer
Absorption correction	Multi-scan (SADABS; Bruker, 2000)
T_min, T_max	0.946, 0.982
No. of measured, independent and observed [I > 2σ(I)] reflections	7817, 2904, 2069
R_int	0.034
(sin θ/λ)_max (Å⁻¹)	0.606

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.047, 0.119, 1.02
No. of reflections	2904
No. of parameters	193
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.23, −0.17

Computer programs: SMART (Bruker, 2000), SAINT (Bruker, 2000), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), SHELXTL (Sheldrick, 2008), PARST (Nardelli, 1995) and PLATON (Spek, 2003).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N2—H2···O1	0.86	2.03	2.706	135
C17—H17B···S1	0.96	2.80	3.496	130
N1—H1···S1ⁱ	0.86	2.57	3.372	155

Symmetry code: (i) −x, −y+1, −z+1.

Acknowledgements

The authors thank the Ministry of Higher Education of Malaysia for Fundamental Research Grants OUP UKM-OUP-BIT-28/20076 and UMT-FRGS-59001, and Universiti Kebangsaan Malaysia and HEJ Research Institute of Chemistry, University of Karachi, for research facilities.

References

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