N-(2,6-Dichloro­phen­yl)-2-(naphthalen-1-yl)acetamide

Fun, H.-K.; Quah, C.K.; Nayak, P.S.; Narayana, B.; Sarojini, B.K.

doi:10.1107/S1600536812014869

organic compounds

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ISSN: 2056-9890

Volume 68| Part 5| May 2012| Page o1385

doi:10.1107/S1600536812014869

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N-(2,6-Dichlorophenyl)-2-(naphthalen-1-yl)acetamide

Hoong-Kun Fun,^a ^*‡ Ching Kheng Quah,^a § Prakash S. Nayak,^b B. Narayana ^b and B. K. Sarojini ^c

^aX-ray Crystallography Unit, School of Physics, Universiti Sains Malaysia, 11800 USM, Penang, Malaysia, ^bDepartment of Studies in Chemistry, Mangalore University, Mangalagangotri 574 199, India, and ^cDepartment of Chemistry, P. A. College of Engineering, Nadupadavu, Mangalore 574 153, India
^*Correspondence e-mail: hkfun@usm.my

(Received 4 April 2012; accepted 4 April 2012; online 13 April 2012)

In the title compound, C₁₈H₁₃Cl₂NO, the naphthalene ring system and the benzene ring form dihedral angles of 74.73 (13) and 62.53 (16)°, respectively, with the acetamide grouping [maximum deviation = 0.005 (3) Å]. The naphthalene ring system forms a dihedral angle of 75.14 (13)° with the benzene ring. In the crystal, molecules are linked by N—H⋯O hydrogen bonds, forming C(4) chains propagating in [010]. The O atom also accepts two C—H⋯O interactions.

Related literature

For related structures, see: Fun et al. (2010 , 2011a ,b ). For the stability of the temperature controller used in the data collection, see: Cosier & Glazer (1986 ).

Experimental

Crystal data

C₁₈H₁₃Cl₂NO
M_r = 330.19
Monoclinic, P 2₁ /c
a = 13.1918 (13) Å
b = 4.7199 (5) Å
c = 24.878 (2) Å
β = 103.127 (3)°
V = 1508.5 (3) Å³
Z = 4
Mo Kα radiation
μ = 0.43 mm⁻¹
T = 100 K
0.38 × 0.13 × 0.08 mm

Data collection

Bruker SMART APEXII CCD diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2009 ) T_min = 0.853, T_max = 0.968
13545 measured reflections
4397 independent reflections
3245 reflections with I > 2σ(I)
R_int = 0.055

Refinement

R[F² > 2σ(F²)] = 0.068
wR(F²) = 0.168
S = 1.08
4397 reflections
203 parameters
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.53 e Å⁻³
Δρ_min = −0.56 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1N1⋯O1ⁱ	0.84 (4)	2.00 (4)	2.823 (3)	165 (3)
C8—H8A⋯O1ⁱ	0.99	2.37	3.242 (4)	146
C8—H8B⋯O1ⁱⁱ	0.99	2.53	3.488 (4)	163
Symmetry codes: (i) x, y+1, z; (ii) -x+1, -y, -z+2.

Data collection: APEX2 (Bruker, 2009); cell refinement: SAINT (Bruker, 2009); data reduction: SAINT; program(s) used to solve structure: SHELXTL (Sheldrick, 2008 ); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL and PLATON (Spek, 2009 ).

Supporting information

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536812014869/hb6731sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536812014869/hb6731Isup2.hkl

Supporting information file. DOI: 10.1107/S1600536812014869/hb6731Isup3.cml

checkCIF report

Comment top

In continuation of our work on synthesis and structures of amides (Fun et al., 2010, 2011a,b) we report herein the crystal structure of the title compound.

The molecular structure is shown in Fig. 1. Bond lengths are comparable to related structures (Fun et al., 2010, 2011a,b). The naphthalene ring system (C9-C18, maximum deviation of 0.017 (3) Å at atom C9) and the benzene ring (C1-C6) form dihedral angles of 74.73 (13) and 62.53 (16)°, respectively, with the acetamide moiety (O1/N1/C7/C8, maximum deviation of 0.005 (3) Å at atom C7). The naphthalene ring system forms a dihedral angle of 75.14 (13)° with the benzene ring.

In the crystal, Fig. 2, molecules are linked via N1–H1N1···O1, C8–H8A···O1 and C8–H8B···O1 hydrogen bonds (Table 1) into two-molecule-thick chains along [010].

Related literature top

For related structures, see: Fun et al. (2010, 2011a,b). For the stability of the temperature controller used in the data collection, see: Cosier & Glazer (1986).

Experimental top

1-Naphthalene acetic acid (0.186 g, 1 mmol) and 2,6-dichloroaniline (0.162 g, 1 mmol), 1-ethyl-3-(3-dimethylaminopropyl)-carbodiimide hydrochloride (1.0 g, 0.01 mol) and were dissolved in dichloromethane (20ml). The mixture was stirred in presence of triethylamine at 273 K for about 3 h. The contents were poured into 100 ml of ice-cold aqueous hydrochloric acid with stirring, which was extracted thrice with dichloromethane. Organic layer was washed with saturated NaHCO₃ solution and brine solution, dried and concentrated under reduced pressure to give the title compound. Colourless needles were grown from N,N-dimethyl formamide solution by the slow evaporation method (m.p.: 463K).

Computing details top

Data collection: APEX2 (Bruker, 2009); cell refinement: SAINT (Bruker, 2009); data reduction: SAINT (Bruker, 2009); program(s) used to solve structure: SHELXTL (Sheldrick, 2008); program(s) used to refine structure: SHELXTL (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXTL (Sheldrick, 2008) and PLATON (Spek, 2009).

Figures top

	Fig. 1. The molecular structure of the title compound showing 50% probability displacement ellipsoids for non-H atoms.
	Fig. 2. The crystal structure of the title compound, viewed along the a axis. H atoms not involved in hydrogen bonds (dashed lines) have been omitted for clarity.

N-(2,6-Dichlorophenyl)-2-(naphthalen-1-yl)acetamide top

Crystal data top

C₁₈H₁₃Cl₂NO	F(000) = 680
M_r = 330.19	D_x = 1.454 Mg m⁻³
Monoclinic, P2₁/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 3979 reflections
a = 13.1918 (13) Å	θ = 3.2–30.0°
b = 4.7199 (5) Å	µ = 0.43 mm⁻¹
c = 24.878 (2) Å	T = 100 K
β = 103.127 (3)°	Needle, colourless
V = 1508.5 (3) Å³	0.38 × 0.13 × 0.08 mm
Z = 4

Data collection top

Bruker SMART APEXII CCD diffractometer	4397 independent reflections
Radiation source: fine-focus sealed tube	3245 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.055
ϕ and ω scans	θ_max = 30.1°, θ_min = 2.0°
Absorption correction: multi-scan (SADABS; Bruker, 2009)	h = −18→18
T_min = 0.853, T_max = 0.968	k = −6→6
13545 measured reflections	l = −35→35

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)] = 0.068	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.168	H atoms treated by a mixture of independent and constrained refinement
S = 1.08	w = 1/[σ²(F_o²) + (0.0606P)² + 3.359P] where P = (F_o² + 2F_c²)/3
4397 reflections	(Δ/σ)_max = 0.001
203 parameters	Δρ_max = 0.53 e Å⁻³
0 restraints	Δρ_min = −0.56 e Å⁻³

Crystal data top

C₁₈H₁₃Cl₂NO	V = 1508.5 (3) Å³
M_r = 330.19	Z = 4
Monoclinic, P2₁/c	Mo Kα radiation
a = 13.1918 (13) Å	µ = 0.43 mm⁻¹
b = 4.7199 (5) Å	T = 100 K
c = 24.878 (2) Å	0.38 × 0.13 × 0.08 mm
β = 103.127 (3)°

Data collection top

Bruker SMART APEXII CCD diffractometer	4397 independent reflections
Absorption correction: multi-scan (SADABS; Bruker, 2009)	3245 reflections with I > 2σ(I)
T_min = 0.853, T_max = 0.968	R_int = 0.055
13545 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.068	0 restraints
wR(F²) = 0.168	H atoms treated by a mixture of independent and constrained refinement
S = 1.08	Δρ_max = 0.53 e Å⁻³
4397 reflections	Δρ_min = −0.56 e Å⁻³
203 parameters

Special details top

Experimental. The crystal was placed in the cold stream of an Oxford Cryosystems Cobra open-flow nitrogen cryostat (Cosier & Glazer, 1986) operating at 100.0 (1) K.

Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds 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 > 2sigma(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	0.46301 (6)	0.58083 (17)	1.15354 (3)	0.02081 (18)
Cl2	0.13465 (6)	−0.0073 (2)	1.03531 (3)	0.0258 (2)
O1	0.36215 (16)	−0.0699 (5)	1.02088 (9)	0.0167 (4)
N1	0.32626 (19)	0.3664 (5)	1.04970 (10)	0.0128 (5)
C1	0.3584 (2)	0.3527 (7)	1.15041 (12)	0.0160 (6)
C2	0.3352 (2)	0.2594 (8)	1.19925 (13)	0.0221 (7)
H2A	0.3758	0.3204	1.2339	0.026*
C3	0.2519 (3)	0.0759 (8)	1.19680 (14)	0.0247 (7)
H3A	0.2357	0.0096	1.2299	0.030*
C4	0.1922 (3)	−0.0109 (7)	1.14604 (14)	0.0234 (7)
H4A	0.1355	−0.1375	1.1444	0.028*
C5	0.2158 (2)	0.0887 (7)	1.09772 (13)	0.0186 (6)
C6	0.3005 (2)	0.2685 (6)	1.09881 (11)	0.0136 (5)
C7	0.3562 (2)	0.1873 (6)	1.01372 (11)	0.0123 (5)
C8	0.3845 (2)	0.3240 (6)	0.96339 (11)	0.0125 (5)
H8A	0.3733	0.5311	0.9645	0.015*
H8B	0.4592	0.2910	0.9649	0.015*
C9	0.3199 (2)	0.2055 (6)	0.90964 (11)	0.0128 (5)
C10	0.3612 (2)	0.0027 (7)	0.88140 (12)	0.0156 (6)
H10A	0.4293	−0.0667	0.8965	0.019*
C11	0.3044 (2)	−0.1058 (7)	0.83020 (12)	0.0183 (6)
H11A	0.3343	−0.2474	0.8114	0.022*
C12	0.2067 (2)	−0.0057 (7)	0.80799 (12)	0.0177 (6)
H12A	0.1691	−0.0769	0.7735	0.021*
C13	0.1607 (2)	0.2029 (6)	0.83576 (12)	0.0151 (6)
C14	0.0590 (2)	0.3104 (7)	0.81287 (12)	0.0189 (6)
H14A	0.0213	0.2416	0.7782	0.023*
C15	0.0150 (2)	0.5103 (8)	0.83999 (13)	0.0213 (6)
H15A	−0.0527	0.5800	0.8240	0.026*
C16	0.0700 (2)	0.6148 (7)	0.89197 (13)	0.0199 (6)
H16A	0.0387	0.7521	0.9110	0.024*
C17	0.1686 (2)	0.5172 (7)	0.91479 (12)	0.0171 (6)
H17A	0.2052	0.5902	0.9494	0.021*
C18	0.2165 (2)	0.3100 (6)	0.88767 (12)	0.0140 (5)
H1N1	0.332 (3)	0.543 (8)	1.0462 (14)	0.014 (9)*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Cl1	0.0224 (3)	0.0174 (4)	0.0219 (4)	−0.0038 (3)	0.0033 (3)	−0.0046 (3)
Cl2	0.0198 (3)	0.0294 (5)	0.0285 (4)	−0.0066 (3)	0.0058 (3)	−0.0084 (3)
O1	0.0234 (10)	0.0077 (10)	0.0203 (10)	0.0022 (8)	0.0077 (8)	−0.0007 (8)
N1	0.0208 (11)	0.0034 (12)	0.0152 (11)	0.0017 (9)	0.0057 (9)	0.0020 (9)
C1	0.0189 (13)	0.0116 (14)	0.0176 (13)	0.0024 (11)	0.0045 (10)	0.0000 (11)
C2	0.0277 (15)	0.0230 (18)	0.0161 (14)	0.0069 (14)	0.0062 (11)	0.0013 (13)
C3	0.0322 (16)	0.0236 (18)	0.0224 (15)	0.0066 (15)	0.0148 (13)	0.0064 (14)
C4	0.0271 (15)	0.0159 (16)	0.0317 (17)	0.0004 (13)	0.0163 (13)	0.0055 (14)
C5	0.0205 (13)	0.0154 (15)	0.0211 (14)	0.0029 (12)	0.0070 (11)	−0.0011 (12)
C6	0.0196 (13)	0.0059 (13)	0.0170 (13)	0.0030 (11)	0.0077 (10)	0.0021 (10)
C7	0.0132 (11)	0.0091 (13)	0.0142 (12)	0.0003 (10)	0.0021 (9)	−0.0017 (11)
C8	0.0161 (12)	0.0068 (12)	0.0148 (12)	−0.0002 (10)	0.0041 (10)	−0.0002 (10)
C9	0.0161 (12)	0.0091 (13)	0.0139 (12)	−0.0023 (11)	0.0051 (10)	0.0015 (11)
C10	0.0182 (12)	0.0120 (14)	0.0172 (13)	−0.0008 (12)	0.0052 (10)	0.0002 (11)
C11	0.0257 (14)	0.0131 (15)	0.0174 (13)	0.0008 (12)	0.0075 (11)	−0.0030 (12)
C12	0.0238 (14)	0.0140 (14)	0.0146 (13)	−0.0025 (12)	0.0032 (10)	−0.0021 (12)
C13	0.0192 (13)	0.0108 (14)	0.0154 (13)	−0.0045 (11)	0.0042 (10)	0.0009 (11)
C14	0.0200 (13)	0.0174 (16)	0.0175 (14)	−0.0017 (12)	0.0004 (11)	0.0010 (12)
C15	0.0151 (12)	0.0230 (17)	0.0248 (15)	0.0009 (12)	0.0029 (11)	0.0031 (13)
C16	0.0220 (14)	0.0157 (16)	0.0231 (15)	0.0017 (12)	0.0075 (11)	−0.0010 (12)
C17	0.0208 (13)	0.0136 (14)	0.0175 (13)	0.0006 (12)	0.0054 (10)	−0.0002 (12)
C18	0.0164 (12)	0.0098 (13)	0.0164 (13)	−0.0009 (11)	0.0053 (10)	0.0006 (11)

Geometric parameters (Å, º) top

Cl1—C1	1.738 (3)	C9—C10	1.371 (4)
Cl2—C5	1.734 (3)	C9—C18	1.436 (4)
O1—C7	1.227 (4)	C10—C11	1.418 (4)
N1—C7	1.354 (4)	C10—H10A	0.9500
N1—C6	1.418 (4)	C11—C12	1.367 (4)
N1—H1N1	0.85 (4)	C11—H11A	0.9500
C1—C2	1.390 (4)	C12—C13	1.416 (4)
C1—C6	1.394 (4)	C12—H12A	0.9500
C2—C3	1.390 (5)	C13—C18	1.426 (4)
C2—H2A	0.9500	C13—C14	1.426 (4)
C3—C4	1.390 (5)	C14—C15	1.364 (5)
C3—H3A	0.9500	C14—H14A	0.9500
C4—C5	1.390 (4)	C15—C16	1.420 (4)
C4—H4A	0.9500	C15—H15A	0.9500
C5—C6	1.398 (4)	C16—C17	1.375 (4)
C7—C8	1.528 (4)	C16—H16A	0.9500
C8—C9	1.520 (4)	C17—C18	1.416 (4)
C8—H8A	0.9900	C17—H17A	0.9500
C8—H8B	0.9900

C7—N1—C6	122.0 (3)	C10—C9—C18	119.9 (3)
C7—N1—H1N1	120 (2)	C10—C9—C8	119.9 (3)
C6—N1—H1N1	117 (2)	C18—C9—C8	120.2 (2)
C2—C1—C6	122.1 (3)	C9—C10—C11	121.5 (3)
C2—C1—Cl1	119.1 (2)	C9—C10—H10A	119.3
C6—C1—Cl1	118.8 (2)	C11—C10—H10A	119.3
C3—C2—C1	119.2 (3)	C12—C11—C10	119.7 (3)
C3—C2—H2A	120.4	C12—C11—H11A	120.2
C1—C2—H2A	120.4	C10—C11—H11A	120.2
C4—C3—C2	120.2 (3)	C11—C12—C13	120.8 (3)
C4—C3—H3A	119.9	C11—C12—H12A	119.6
C2—C3—H3A	119.9	C13—C12—H12A	119.6
C3—C4—C5	119.6 (3)	C12—C13—C18	119.9 (3)
C3—C4—H4A	120.2	C12—C13—C14	121.4 (3)
C5—C4—H4A	120.2	C18—C13—C14	118.7 (3)
C4—C5—C6	121.6 (3)	C15—C14—C13	121.1 (3)
C4—C5—Cl2	118.1 (3)	C15—C14—H14A	119.5
C6—C5—Cl2	120.3 (2)	C13—C14—H14A	119.5
C1—C6—C5	117.3 (3)	C14—C15—C16	120.3 (3)
C1—C6—N1	120.8 (3)	C14—C15—H15A	119.9
C5—C6—N1	121.9 (3)	C16—C15—H15A	119.9
O1—C7—N1	122.7 (3)	C17—C16—C15	120.0 (3)
O1—C7—C8	121.2 (3)	C17—C16—H16A	120.0
N1—C7—C8	116.1 (3)	C15—C16—H16A	120.0
C9—C8—C7	111.9 (2)	C16—C17—C18	121.1 (3)
C9—C8—H8A	109.2	C16—C17—H17A	119.4
C7—C8—H8A	109.2	C18—C17—H17A	119.4
C9—C8—H8B	109.2	C17—C18—C13	118.8 (3)
C7—C8—H8B	109.2	C17—C18—C9	122.9 (3)
H8A—C8—H8B	107.9	C13—C18—C9	118.2 (3)

C6—C1—C2—C3	0.1 (5)	C18—C9—C10—C11	0.7 (4)
Cl1—C1—C2—C3	−179.7 (3)	C8—C9—C10—C11	−177.9 (3)
C1—C2—C3—C4	−0.5 (5)	C9—C10—C11—C12	0.5 (5)
C2—C3—C4—C5	−0.5 (5)	C10—C11—C12—C13	−0.8 (5)
C3—C4—C5—C6	1.9 (5)	C11—C12—C13—C18	−0.2 (5)
C3—C4—C5—Cl2	−176.1 (3)	C11—C12—C13—C14	179.6 (3)
C2—C1—C6—C5	1.2 (4)	C12—C13—C14—C15	179.7 (3)
Cl1—C1—C6—C5	−178.9 (2)	C18—C13—C14—C15	−0.5 (5)
C2—C1—C6—N1	−179.8 (3)	C13—C14—C15—C16	−0.2 (5)
Cl1—C1—C6—N1	0.1 (4)	C14—C15—C16—C17	0.9 (5)
C4—C5—C6—C1	−2.3 (4)	C15—C16—C17—C18	−0.8 (5)
Cl2—C5—C6—C1	175.8 (2)	C16—C17—C18—C13	0.1 (5)
C4—C5—C6—N1	178.7 (3)	C16—C17—C18—C9	179.0 (3)
Cl2—C5—C6—N1	−3.2 (4)	C12—C13—C18—C17	−179.6 (3)
C7—N1—C6—C1	117.3 (3)	C14—C13—C18—C17	0.5 (4)
C7—N1—C6—C5	−63.7 (4)	C12—C13—C18—C9	1.4 (4)
C6—N1—C7—O1	0.6 (4)	C14—C13—C18—C9	−178.4 (3)
C6—N1—C7—C8	−178.3 (2)	C10—C9—C18—C17	179.4 (3)
O1—C7—C8—C9	57.7 (3)	C8—C9—C18—C17	−2.0 (4)
N1—C7—C8—C9	−123.3 (3)	C10—C9—C18—C13	−1.7 (4)
C7—C8—C9—C10	−99.9 (3)	C8—C9—C18—C13	176.9 (3)
C7—C8—C9—C18	81.5 (3)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1N1···O1ⁱ	0.84 (4)	2.00 (4)	2.823 (3)	165 (3)
C8—H8A···O1ⁱ	0.99	2.37	3.242 (4)	146
C8—H8B···O1ⁱⁱ	0.99	2.53	3.488 (4)	163

Symmetry codes: (i) x, y+1, z; (ii) −x+1, −y, −z+2.

Experimental details

Crystal data
Chemical formula	C₁₈H₁₃Cl₂NO
M_r	330.19
Crystal system, space group	Monoclinic, P2₁/c
Temperature (K)	100
a, b, c (Å)	13.1918 (13), 4.7199 (5), 24.878 (2)
β (°)	103.127 (3)
V (Å³)	1508.5 (3)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.43
Crystal size (mm)	0.38 × 0.13 × 0.08

Data collection
Diffractometer	Bruker SMART APEXII CCD diffractometer
Absorption correction	Multi-scan (SADABS; Bruker, 2009)
T_min, T_max	0.853, 0.968
No. of measured, independent and observed [I > 2σ(I)] reflections	13545, 4397, 3245
R_int	0.055
(sin θ/λ)_max (Å⁻¹)	0.706

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.068, 0.168, 1.08
No. of reflections	4397
No. of parameters	203
H-atom treatment	H atoms treated by a mixture of independent and constrained refinement
Δρ_max, Δρ_min (e Å⁻³)	0.53, −0.56

Computer programs: APEX2 (Bruker, 2009), SAINT (Bruker, 2009), SHELXTL (Sheldrick, 2008) and PLATON (Spek, 2009).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1N1···O1ⁱ	0.84 (4)	2.00 (4)	2.823 (3)	165 (3)
C8—H8A···O1ⁱ	0.99	2.37	3.242 (4)	146
C8—H8B···O1ⁱⁱ	0.99	2.53	3.488 (4)	163

Symmetry codes: (i) x, y+1, z; (ii) −x+1, −y, −z+2.

Footnotes

‡Thomson Reuters ResearcherID: A-3561-2009.

§Thomson Reuters ResearcherID: A-5525-2009.

Acknowledgements

The authors would like to thank Universiti Sains Malaysia for the Research University Grant (No. 1001/PFIZIK/811160). BN thanks the UGC, New Delhi, and the Government of India for the purchase of chemicals through the SAP–DRS–Phase 1 programme.

References

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