N-[4-(4-Chloro­benzene­sulfonamido)­phenyl­sulfon­yl]acetamide

Khan, I.U.; Ejaz; Farid, S.; Harrison, W.T.A.

doi:10.1107/S1600536812023434

organic compounds

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ISSN: 2056-9890

Volume 68| Part 6| June 2012| Page o1913

doi:10.1107/S1600536812023434

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N-[4-(4-Chlorobenzenesulfonamido)phenylsulfonyl]acetamide

Islam Ullah Khan,^a ^* Ejaz,^a Sidra Farid ^a and William T. A. Harrison ^b

^aMaterials Chemistry Laboratry, Department of Chemistry, GC University, Lahore 54000, Pakistan, and ^bDepartment of Chemistry, University of Aberdeen, Meston Walk, Aberdeen AB24 3UE, Scotland
^*Correspondence e-mail: iuklodhi@yahoo.com

(Received 17 May 2012; accepted 22 May 2012; online 26 May 2012)

In the title compound, C₁₄H₁₃ClN₂O₅S₂, the dihedral angles between the central benzene ring and the pendant chlorobenzene ring and the N-acetyl group are 82.35 (5) and 79.71 (6)°, respectively, and the overall conformation of the molecule approximates to a U shape. Both the C—S—N—C conformations are gauche, but with opposite senses [torsion angles = −59.29 (15) and 63.68 (16)°]. An intramolecular C—H⋯O interaction generates an S(6) ring. In the crystal, inversion dimers linked by pairs of N—H⋯O hydrogen bonds generate R₂²(20) loops. A second N—H⋯O hydrogen bond links the dimers into (101) layers.

Related literature

For related structures, see: Ashfaq et al. (2009 , 2010 ).

Experimental

Crystal data

C₁₄H₁₃ClN₂O₅S₂
M_r = 388.83
Monoclinic, P 2₁ /n
a = 9.7452 (2) Å
b = 9.9905 (2) Å
c = 17.3968 (3) Å
β = 99.870 (1)°
V = 1668.67 (6) Å³
Z = 4
Mo Kα radiation
μ = 0.51 mm⁻¹
T = 296 K
0.40 × 0.20 × 0.10 mm

Data collection

Bruker APEXII CCD diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2007 ) T_min = 0.823, T_max = 0.951
15966 measured reflections
4146 independent reflections
3267 reflections with I > 2σ(I)
R_int = 0.026

Refinement

R[F² > 2σ(F²)] = 0.034
wR(F²) = 0.092
S = 1.03
4146 reflections
226 parameters
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.30 e Å⁻³
Δρ_min = −0.37 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1⋯O5ⁱ	0.85 (2)	1.97 (2)	2.8070 (19)	166 (2)
N2—H2⋯O1ⁱⁱ	0.87 (2)	2.10 (2)	2.9510 (19)	166.3 (19)
C12—H12⋯O2	0.93	2.44	3.074 (2)	126
Symmetry codes: (i) -x+1, -y, -z+1; (ii) $[x+{\script{1\over 2}}, -y+{\script{1\over 2}}, z-{\script{1\over 2}}]$ .

Data collection: APEX2 (Bruker, 2007); cell refinement: SAINT (Bruker, 2007); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 (Farrugia, 1997 ); software used to prepare material for publication: SHELXL97.

Supporting information

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536812023434/su2434sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536812023434/su2434Isup2.hkl

Supporting information file. DOI: 10.1107/S1600536812023434/su2434Isup3.cml

checkCIF report

Comment top

As part of our ongoing structural studies of sulfonamides (Ashfaq et al., 2009, 2010), the synthesis and structure of the title compound, (I), (Fig. 1), are now described.

The dihedral angle between the central (C7—C12) benzene ring and the pendant (C1—C6) chlorobenzene ring is 82.35 (50)°. The dihedral angle between the central ring and the C13/C14/N2/O5 amide fragment is 79.71 (60)°, and overall, the molecule adpots an approximate U shape. The conformation of the C1—S1—N1—C7 fragment is gauche [-59.29 (15)°], and the torsion angle for C10—S2—N2—C13 of 63.68 (16)° indicates the same thing, but in an opposite sense. The bond-angle sums for N1 and N2 are 351.4 and 360.0°, respectively. An intramolecular C—H···O interaction (Table 1) generates an S(6) ring.

In the crystal, inversion dimers linked by pairs of N—H···O hydrogen bonds generate R₂²(20) loops (Fig. 2). The other N—H···O hydrogen bonds links the dimers into (101) layers. Centrosymmetric R₂²(20) loops were also observed in the crystal structures of the related compounds N-acetyl-4-(benzenesulfonamido)-benzenesulfonamide (Ashfaq et al., 2009) and N-[4-(p-toluenesulfonamido)phenylsulfonyl]acetamide (Ashfaq et al., 2010).

Related literature top

For related structures, see: Ashfaq et al. (2009, 2010).

Experimental top

Sodium sulfacetamide (0.236 g, 1.0 mmol) was dissolved in 30 ml distllled water in a 100-ml round bottom flask and the pH was adjusted to 8.0 using Na₂CO₃ solution (3%). 4-Chlorobenzenesulfonyl chloride (0.422 g, 2.0 mmol) was added and the mixture was stirred at 50 °C for about 5 h. The pH was adjusted to 3.0 using HCl (3 N) and the resulting white precipitate was filtered, washed and dried. Colourless blocks of (I) were recrystallized from methanol solution at room temperature. This compound has been deposited to CSD with CCDC No. 859957.

Computing details top

Data collection: APEX2 (Bruker, 2007); cell refinement: SAINT (Bruker, 2007); data reduction: SAINT (Bruker, 2007); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 (Farrugia, 1997); software used to prepare material for publication: SHELXL97 (Sheldrick, 2008).

Figures top

	Fig. 1. The molecular structure of (I) showing 50% displacement ellipsoids.
	Fig. 2. An inversion dimer in the crystal of (I), which generates an R₂²(20) loop. Symmetry code: (i) 1–x, –y, 1–z.

N-[4-(4-Chlorobenzenesulfonamido)phenylsulfonyl]acetamide top

Crystal data top

C₁₄H₁₃ClN₂O₅S₂	F(000) = 800
M_r = 388.83	D_x = 1.548 Mg m⁻³
Monoclinic, P2₁/n	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2yn	Cell parameters from 5590 reflections
a = 9.7452 (2) Å	θ = 2.4–28.1°
b = 9.9905 (2) Å	µ = 0.51 mm⁻¹
c = 17.3968 (3) Å	T = 296 K
β = 99.870 (1)°	Block, colourless
V = 1668.67 (6) Å³	0.40 × 0.20 × 0.10 mm
Z = 4

Data collection top

Bruker APEXII CCD diffractometer	4146 independent reflections
Radiation source: fine-focus sealed tube	3267 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.026
ω scans	θ_max = 28.3°, θ_min = 2.9°
Absorption correction: multi-scan (SADABS; Bruker, 2007)	h = −12→12
T_min = 0.823, T_max = 0.951	k = −13→13
15966 measured reflections	l = −21→23

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)] = 0.034	Hydrogen site location: difmap (N-H) and geom (C-H)
wR(F²) = 0.092	H atoms treated by a mixture of independent and constrained refinement
S = 1.03	w = 1/[σ²(F_o²) + (0.0429P)² + 0.5555P] where P = (F_o² + 2F_c²)/3
4146 reflections	(Δ/σ)_max = 0.001
226 parameters	Δρ_max = 0.30 e Å⁻³
0 restraints	Δρ_min = −0.37 e Å⁻³

Crystal data top

C₁₄H₁₃ClN₂O₅S₂	V = 1668.67 (6) Å³
M_r = 388.83	Z = 4
Monoclinic, P2₁/n	Mo Kα radiation
a = 9.7452 (2) Å	µ = 0.51 mm⁻¹
b = 9.9905 (2) Å	T = 296 K
c = 17.3968 (3) Å	0.40 × 0.20 × 0.10 mm
β = 99.870 (1)°

Data collection top

Bruker APEXII CCD diffractometer	4146 independent reflections
Absorption correction: multi-scan (SADABS; Bruker, 2007)	3267 reflections with I > 2σ(I)
T_min = 0.823, T_max = 0.951	R_int = 0.026
15966 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.034	0 restraints
wR(F²) = 0.092	H atoms treated by a mixture of independent and constrained refinement
S = 1.03	Δρ_max = 0.30 e Å⁻³
4146 reflections	Δρ_min = −0.37 e Å⁻³
226 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
C1	0.20974 (17)	0.33396 (16)	0.55613 (9)	0.0306 (3)
C2	0.18774 (18)	0.44608 (18)	0.50941 (10)	0.0368 (4)
H2A	0.1078	0.4530	0.4718	0.044*
C3	0.2851 (2)	0.54835 (18)	0.51874 (11)	0.0415 (4)
H3	0.2711	0.6248	0.4879	0.050*
C4	0.40247 (19)	0.53498 (18)	0.57432 (11)	0.0402 (4)
C5	0.4280 (2)	0.4213 (2)	0.62017 (11)	0.0449 (5)
H5	0.5095	0.4135	0.6566	0.054*
C6	0.33066 (19)	0.31992 (19)	0.61088 (10)	0.0393 (4)
H6	0.3458	0.2427	0.6410	0.047*
C7	0.21126 (16)	0.06282 (15)	0.44896 (9)	0.0274 (3)
C8	0.30854 (19)	−0.03793 (17)	0.44559 (10)	0.0372 (4)
H8	0.3333	−0.0950	0.4879	0.045*
C9	0.3684 (2)	−0.05378 (18)	0.38001 (11)	0.0404 (4)
H9	0.4333	−0.1213	0.3779	0.048*
C10	0.33119 (17)	0.03193 (16)	0.31703 (9)	0.0315 (3)
C11	0.23330 (18)	0.13100 (17)	0.31958 (10)	0.0335 (4)
H11	0.2084	0.1875	0.2770	0.040*
C12	0.17231 (17)	0.14656 (17)	0.38490 (9)	0.0332 (4)
H12	0.1055	0.2126	0.3862	0.040*
C13	0.65205 (18)	0.12228 (19)	0.30551 (10)	0.0363 (4)
C14	0.7580 (2)	0.2294 (2)	0.30576 (12)	0.0545 (5)
H14A	0.7909	0.2578	0.3584	0.082*
H14B	0.7170	0.3041	0.2755	0.082*
H14C	0.8347	0.1955	0.2835	0.082*
N1	0.15644 (15)	0.07329 (14)	0.51825 (8)	0.0311 (3)
H1	0.202 (2)	0.029 (2)	0.5560 (13)	0.050 (6)*
N2	0.53926 (15)	0.12827 (16)	0.24656 (8)	0.0345 (3)
H2	0.531 (2)	0.191 (2)	0.2111 (12)	0.046 (6)*
O1	0.06025 (14)	0.17153 (13)	0.62438 (7)	0.0432 (3)
O2	−0.03065 (12)	0.24552 (13)	0.48970 (7)	0.0414 (3)
O3	0.46830 (16)	−0.11310 (14)	0.23297 (9)	0.0538 (4)
O4	0.31838 (14)	0.06823 (17)	0.16787 (7)	0.0557 (4)
O5	0.66166 (14)	0.03331 (15)	0.35379 (8)	0.0496 (3)
S1	0.08358 (4)	0.20587 (4)	0.54746 (2)	0.03105 (11)
S2	0.41012 (5)	0.01756 (5)	0.23429 (2)	0.03680 (12)
Cl1	0.52276 (6)	0.66492 (5)	0.58794 (4)	0.06056 (17)

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
C1	0.0309 (8)	0.0310 (8)	0.0301 (8)	0.0009 (6)	0.0061 (7)	−0.0060 (6)
C2	0.0343 (9)	0.0359 (9)	0.0386 (9)	0.0022 (7)	0.0018 (7)	−0.0008 (7)
C3	0.0452 (10)	0.0318 (9)	0.0481 (11)	0.0008 (8)	0.0099 (8)	0.0002 (8)
C4	0.0373 (10)	0.0349 (9)	0.0499 (11)	−0.0063 (7)	0.0119 (8)	−0.0139 (8)
C5	0.0354 (10)	0.0495 (11)	0.0452 (11)	−0.0022 (8)	−0.0062 (8)	−0.0064 (8)
C6	0.0397 (10)	0.0391 (9)	0.0368 (9)	0.0019 (8)	−0.0002 (8)	0.0023 (7)
C7	0.0270 (8)	0.0265 (7)	0.0285 (8)	−0.0034 (6)	0.0041 (6)	−0.0032 (6)
C8	0.0440 (10)	0.0324 (9)	0.0369 (9)	0.0080 (8)	0.0118 (8)	0.0081 (7)
C9	0.0444 (10)	0.0335 (9)	0.0462 (10)	0.0103 (8)	0.0160 (8)	0.0034 (7)
C10	0.0316 (8)	0.0331 (8)	0.0305 (8)	−0.0031 (7)	0.0075 (7)	−0.0047 (6)
C11	0.0358 (9)	0.0357 (9)	0.0276 (8)	0.0016 (7)	0.0013 (7)	0.0011 (7)
C12	0.0319 (9)	0.0347 (9)	0.0322 (8)	0.0064 (7)	0.0028 (7)	−0.0001 (7)
C13	0.0341 (9)	0.0478 (10)	0.0278 (8)	−0.0007 (8)	0.0072 (7)	−0.0003 (7)
C14	0.0464 (12)	0.0745 (15)	0.0419 (11)	−0.0209 (11)	0.0057 (9)	−0.0011 (10)
N1	0.0337 (8)	0.0299 (7)	0.0298 (7)	0.0027 (6)	0.0062 (6)	0.0004 (6)
N2	0.0376 (8)	0.0401 (8)	0.0254 (7)	−0.0053 (6)	0.0040 (6)	0.0051 (6)
O1	0.0490 (8)	0.0476 (7)	0.0375 (7)	−0.0043 (6)	0.0200 (6)	−0.0056 (6)
O2	0.0283 (6)	0.0455 (7)	0.0485 (7)	0.0045 (5)	0.0015 (5)	−0.0062 (6)
O3	0.0631 (10)	0.0419 (8)	0.0630 (9)	−0.0060 (7)	0.0300 (7)	−0.0204 (7)
O4	0.0457 (8)	0.0911 (12)	0.0276 (7)	−0.0079 (8)	−0.0012 (6)	−0.0068 (7)
O5	0.0469 (8)	0.0599 (9)	0.0397 (7)	0.0029 (7)	0.0007 (6)	0.0163 (6)
S1	0.0282 (2)	0.0340 (2)	0.0318 (2)	0.00023 (16)	0.00766 (16)	−0.00486 (16)
S2	0.0377 (2)	0.0439 (3)	0.0297 (2)	−0.00666 (19)	0.00829 (17)	−0.01026 (17)
Cl1	0.0523 (3)	0.0466 (3)	0.0847 (4)	−0.0174 (2)	0.0175 (3)	−0.0224 (3)

Geometric parameters (Å, º) top

C1—C2	1.379 (2)	C10—C11	1.381 (2)
C1—C6	1.389 (2)	C10—S2	1.7504 (16)
C1—S1	1.7630 (17)	C11—C12	1.379 (2)
C2—C3	1.385 (3)	C11—H11	0.9300
C2—H2A	0.9300	C12—H12	0.9300
C3—C4	1.372 (3)	C13—O5	1.215 (2)
C3—H3	0.9300	C13—N2	1.370 (2)
C4—C5	1.386 (3)	C13—C14	1.487 (3)
C4—Cl1	1.7380 (18)	C14—H14A	0.9600
C5—C6	1.378 (3)	C14—H14B	0.9600
C5—H5	0.9300	C14—H14C	0.9600
C6—H6	0.9300	N1—S1	1.6249 (14)
C7—C8	1.391 (2)	N1—H1	0.85 (2)
C7—C12	1.393 (2)	N2—S2	1.6615 (15)
C7—N1	1.404 (2)	N2—H2	0.87 (2)
C8—C9	1.377 (2)	O1—S1	1.4369 (13)
C8—H8	0.9300	O2—S1	1.4220 (13)
C9—C10	1.389 (2)	O3—S2	1.4249 (15)
C9—H9	0.9300	O4—S2	1.4270 (15)

C2—C1—C6	120.93 (16)	C10—C11—H11	119.8
C2—C1—S1	120.23 (13)	C11—C12—C7	119.66 (15)
C6—C1—S1	118.84 (13)	C11—C12—H12	120.2
C1—C2—C3	119.74 (17)	C7—C12—H12	120.2
C1—C2—H2A	120.1	O5—C13—N2	120.40 (17)
C3—C2—H2A	120.1	O5—C13—C14	123.58 (17)
C4—C3—C2	118.85 (17)	N2—C13—C14	116.01 (16)
C4—C3—H3	120.6	C13—C14—H14A	109.5
C2—C3—H3	120.6	C13—C14—H14B	109.5
C3—C4—C5	122.09 (17)	H14A—C14—H14B	109.5
C3—C4—Cl1	119.00 (15)	C13—C14—H14C	109.5
C5—C4—Cl1	118.91 (15)	H14A—C14—H14C	109.5
C6—C5—C4	118.85 (17)	H14B—C14—H14C	109.5
C6—C5—H5	120.6	C7—N1—S1	125.47 (12)
C4—C5—H5	120.6	C7—N1—H1	113.3 (15)
C5—C6—C1	119.49 (17)	S1—N1—H1	112.5 (15)
C5—C6—H6	120.3	C13—N2—S2	124.05 (13)
C1—C6—H6	120.3	C13—N2—H2	121.7 (14)
C8—C7—C12	119.68 (14)	S2—N2—H2	114.3 (14)
C8—C7—N1	116.91 (14)	O2—S1—O1	119.66 (8)
C12—C7—N1	123.41 (14)	O2—S1—N1	109.71 (8)
C9—C8—C7	120.46 (16)	O1—S1—N1	104.12 (8)
C9—C8—H8	119.8	O2—S1—C1	107.95 (8)
C7—C8—H8	119.8	O1—S1—C1	108.23 (8)
C8—C9—C10	119.48 (16)	N1—S1—C1	106.43 (7)
C8—C9—H9	120.3	O3—S2—O4	120.51 (9)
C10—C9—H9	120.3	O3—S2—N2	108.49 (8)
C11—C10—C9	120.35 (15)	O4—S2—N2	102.91 (8)
C11—C10—S2	119.25 (13)	O3—S2—C10	108.70 (8)
C9—C10—S2	120.39 (13)	O4—S2—C10	109.52 (8)
C12—C11—C10	120.35 (16)	N2—S2—C10	105.64 (8)
C12—C11—H11	119.8

C6—C1—C2—C3	−2.2 (3)	C12—C7—N1—S1	−21.5 (2)
S1—C1—C2—C3	177.56 (13)	O5—C13—N2—S2	−1.1 (3)
C1—C2—C3—C4	0.5 (3)	C14—C13—N2—S2	178.90 (14)
C2—C3—C4—C5	1.4 (3)	C7—N1—S1—O2	57.26 (15)
C2—C3—C4—Cl1	−178.37 (14)	C7—N1—S1—O1	−173.53 (13)
C3—C4—C5—C6	−1.6 (3)	C7—N1—S1—C1	−59.29 (15)
Cl1—C4—C5—C6	178.15 (14)	C2—C1—S1—O2	−1.39 (16)
C4—C5—C6—C1	0.0 (3)	C6—C1—S1—O2	178.34 (13)
C2—C1—C6—C5	1.9 (3)	C2—C1—S1—O1	−132.27 (14)
S1—C1—C6—C5	−177.80 (14)	C6—C1—S1—O1	47.46 (16)
C12—C7—C8—C9	1.2 (3)	C2—C1—S1—N1	116.33 (14)
N1—C7—C8—C9	−179.22 (16)	C6—C1—S1—N1	−63.94 (15)
C7—C8—C9—C10	0.1 (3)	C13—N2—S2—O3	−52.72 (16)
C8—C9—C10—C11	−1.0 (3)	C13—N2—S2—O4	178.53 (15)
C8—C9—C10—S2	177.83 (14)	C13—N2—S2—C10	63.68 (16)
C9—C10—C11—C12	0.5 (3)	C11—C10—S2—O3	−160.62 (14)
S2—C10—C11—C12	−178.32 (13)	C9—C10—S2—O3	20.54 (17)
C10—C11—C12—C7	0.8 (3)	C11—C10—S2—O4	−27.10 (16)
C8—C7—C12—C11	−1.7 (2)	C9—C10—S2—O4	154.06 (15)
N1—C7—C12—C11	178.78 (15)	C11—C10—S2—N2	83.11 (15)
C8—C7—N1—S1	159.00 (13)	C9—C10—S2—N2	−95.73 (16)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1···O5ⁱ	0.85 (2)	1.97 (2)	2.8070 (19)	166 (2)
N2—H2···O1ⁱⁱ	0.87 (2)	2.10 (2)	2.9510 (19)	166.3 (19)
C12—H12···O2	0.93	2.44	3.074 (2)	126

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

Experimental details

Crystal data
Chemical formula	C₁₄H₁₃ClN₂O₅S₂
M_r	388.83
Crystal system, space group	Monoclinic, P2₁/n
Temperature (K)	296
a, b, c (Å)	9.7452 (2), 9.9905 (2), 17.3968 (3)
β (°)	99.870 (1)
V (Å³)	1668.67 (6)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.51
Crystal size (mm)	0.40 × 0.20 × 0.10

Data collection
Diffractometer	Bruker APEXII CCD diffractometer
Absorption correction	Multi-scan (SADABS; Bruker, 2007)
T_min, T_max	0.823, 0.951
No. of measured, independent and observed [I > 2σ(I)] reflections	15966, 4146, 3267
R_int	0.026
(sin θ/λ)_max (Å⁻¹)	0.667

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.034, 0.092, 1.03
No. of reflections	4146
No. of parameters	226
H-atom treatment	H atoms treated by a mixture of independent and constrained refinement
Δρ_max, Δρ_min (e Å⁻³)	0.30, −0.37

Computer programs: APEX2 (Bruker, 2007), SAINT (Bruker, 2007), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), ORTEP-3 (Farrugia, 1997).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1···O5ⁱ	0.85 (2)	1.97 (2)	2.8070 (19)	166 (2)
N2—H2···O1ⁱⁱ	0.87 (2)	2.10 (2)	2.9510 (19)	166.3 (19)
C12—H12···O2	0.93	2.44	3.074 (2)	126

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

Acknowledgements

IUK thanks the Higher Education Commission of Pakistan for its financial support under the project to strengthen the Materials Chemistry Laboratory at GCUL.

References

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Farrugia, L. J. (1997). J. Appl. Cryst. 30, 565. CrossRef IUCr Journals Google Scholar
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