rac-(3S,4Z)-3-Chloro-4-[2-(3-fluoro­benzyl­idene)hydrazinyl­idene]-1-methyl-3,4-dihydro-1H-2λ6,1-benzothia­zine-2,2-dione

Shafiq, M.; Tahir, M.N.; Khan, I.U.; Ahmad, S.

doi:10.1107/S1600536812021654

organic compounds

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ISSN: 2056-9890

Volume 68| Part 6| June 2012| Page o1787

doi:10.1107/S1600536812021654

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rac-(3S,4Z)-3-Chloro-4-[2-(3-fluorobenzylidene)hydrazinylidene]-1-methyl-3,4-dihydro-1H-2λ⁶,1-benzothiazine-2,2-dione

Muhammad Shafiq,^a M. Nawaz Tahir,^b ^* Islam Ullah Khan ^c and Saeed Ahmad ^d

^aDepartment of Chemistry, Government College University, Faisalabad, Pakistan, ^bUniversity of Sargodha, Department of Physics, Sargodha, Pakistan, ^cMaterials Chemistry Laboratory, Department of Chemistry, Government College University, Lahore, Pakistan, and ^dDepartment of Chemistry, Gomal University, Dera Ismail Khan, K.P.K, Pakistan
^*Correspondence e-mail: dmntahir_uos@yahoo.com

(Received 6 May 2012; accepted 13 May 2012; online 19 May 2012)

In the title compound, C₁₆H₁₃ClFN₃O₂S, the dihedral angle between the benzene rings is 4.47 (3)°. The conformation of the thiazine ring is a half-chair and the Cl atom is in an axial orientation. In the crystal, molecules are linked by C—H⋯F interactions, generating C(12) chains propagating in [011]. Aromatic π–π stacking interactions [centroid–centroid separations = 3.753 (2) and 3.758 (2) Å] also occur.

Related literature

For a related structure and background references, see: Shafiq et al. (2012 ). For further synthetic details, see: Shafiq et al. (2011a ,b ). For ring conformations, see: Cremer & Pople (1975 ).

Experimental

Crystal data

C₁₆H₁₃ClFN₃O₂S
M_r = 365.80
Triclinic, $[P \overline 1]$
a = 7.0072 (3) Å
b = 8.9402 (4) Å
c = 13.3438 (6) Å
α = 98.184 (3)°
β = 90.510 (2)°
γ = 98.389 (3)°
V = 818.19 (6) Å³
Z = 2
Mo Kα radiation
μ = 0.39 mm⁻¹
T = 296 K
0.26 × 0.18 × 0.12 mm

Data collection

Bruker Kappa APEXII CCD diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2005 ) T_min = 0.930, T_max = 0.960
11874 measured reflections
2941 independent reflections
1744 reflections with I > 2σ(I)
R_int = 0.065

Refinement

R[F² > 2σ(F²)] = 0.050
wR(F²) = 0.120
S = 1.00
2941 reflections
218 parameters
H-atom parameters constrained
Δρ_max = 0.33 e Å⁻³
Δρ_min = −0.32 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C5—H5⋯F1ⁱ	0.93	2.53	3.442 (5)	167
Symmetry code: (i) x, y-1, z-1.

Data collection: APEX2 (Bruker, 2009 ); cell refinement: SAINT (Bruker, 2009); 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 for Windows (Farrugia, 1997 ) and PLATON (Spek, 2009 ); software used to prepare material for publication: WinGX (Farrugia, 1999 ) and PLATON.

Supporting information

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536812021654/hb6778sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536812021654/hb6778Isup2.hkl

Supporting information file. DOI: 10.1107/S1600536812021654/hb6778Isup3.cml

checkCIF report

Comment top

As part of our ongoing synthetic and structural studies of thiazine derivatives (Shafiq et al., 2012), we now describe the title compound, (I), (Fig. 1).

In (I), the benzene rings A (C1—C6) and B (C10—C15) are planar with r. m. s. deviation of 0.0040 and 0.0012 Å, respectively. The dihedral angle between A/B is 4.47 (3)°. The central group C (N2/N3/C9) is of course planar. The dihedral angle between A/C and B/C is 5.87 (7) and 1.48 (8)°, respectively. The thiazine ring D (C1/C6/N1/S1/C7/C8) is in the half-chair form, with the maximum puckering amplitude (Cremer & Pople, 1975), Q = 0.563 (3) Å. In the crystal, the molecules form chains due to H-bonding of C—H···F type (Table 1, Fig. 2). There exist π–π interactions between CgA···CgBⁱ [i = 1 - x, -y, 1 - z] and CgB···CgAⁱⁱ [ii = 2 - x, -y, 1 - z] at a distance of 3.758 (2) and 3.753 (2) Å, where CgA and CgB are the centroids of benzene rings A and B, respectively.

Related literature top

For a related structure and background references, see: Shafiq et al. (2012). For further synthetic details, see: Shafiq et al. (2011a,b). For ring conformations, see: Cremer & Pople (1975).

Experimental top

The Schiff base derivative of (4Z)-4-hydrazinylidene-1-methyl-3,4-dihydro -1H-2,1-benzothiazine 2,2-dioxide and 3-flourobenzaldehyde was prepared using the method reported previously (Shafiq et al. 2011b). The chlorination of the schiff base was undertaken using N-chloro succinimide and dibenzoylperoxide (Shafiq et al., 2011a). The crude product of (I) was re-crystallized in ethyl acetate to obtain yellow needles of the title compound.

Computing details top

Data collection: APEX2 (Bruker, 2009); cell refinement: SAINT (Bruker, 2009); data reduction: SAINT (Bruker, 2009); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997) and PLATON (Spek, 2009); software used to prepare material for publication: WinGX (Farrugia, 1999) and PLATON (Spek, 2009).

Figures top

	Fig. 1. View of the title compound with displacement ellipsoids drawn at the 50% probability level.
	Fig. 2. Partial packing diagram showing polymeric chains.

rac-(3S,4Z)-3-Chloro-4-[2-(3- fluorobenzylidene)hydrazinylidene]- 3-chloro-1-methyl-3,4-dihydro-1H-2λ⁶,1-benzothiazine-2,2-dione top

Crystal data top

C₁₆H₁₃ClFN₃O₂S	Z = 2
M_r = 365.80	F(000) = 376
Triclinic, P1	D_x = 1.485 Mg m⁻³
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 7.0072 (3) Å	Cell parameters from 1744 reflections
b = 8.9402 (4) Å	θ = 2.3–25.3°
c = 13.3438 (6) Å	µ = 0.39 mm⁻¹
α = 98.184 (3)°	T = 296 K
β = 90.510 (2)°	Needle, yellow
γ = 98.389 (3)°	0.26 × 0.18 × 0.12 mm
V = 818.19 (6) Å³

Data collection top

Bruker Kappa APEXII CCD diffractometer	2941 independent reflections
Radiation source: fine-focus sealed tube	1744 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.065
Detector resolution: 8.10 pixels mm^-1	θ_max = 25.3°, θ_min = 2.3°
ω scans	h = −8→8
Absorption correction: multi-scan (SADABS; Bruker, 2005)	k = −10→10
T_min = 0.930, T_max = 0.960	l = −16→16
11874 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)] = 0.050	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.120	H-atom parameters constrained
S = 1.00	w = 1/[σ²(F_o²) + (0.0478P)² + 0.0889P] where P = (F_o² + 2F_c²)/3
2941 reflections	(Δ/σ)_max < 0.001
218 parameters	Δρ_max = 0.33 e Å⁻³
0 restraints	Δρ_min = −0.32 e Å⁻³

Crystal data top

C₁₆H₁₃ClFN₃O₂S	γ = 98.389 (3)°
M_r = 365.80	V = 818.19 (6) Å³
Triclinic, P1	Z = 2
a = 7.0072 (3) Å	Mo Kα radiation
b = 8.9402 (4) Å	µ = 0.39 mm⁻¹
c = 13.3438 (6) Å	T = 296 K
α = 98.184 (3)°	0.26 × 0.18 × 0.12 mm
β = 90.510 (2)°

Data collection top

Bruker Kappa APEXII CCD diffractometer	2941 independent reflections
Absorption correction: multi-scan (SADABS; Bruker, 2005)	1744 reflections with I > 2σ(I)
T_min = 0.930, T_max = 0.960	R_int = 0.065
11874 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.050	0 restraints
wR(F²) = 0.120	H-atom parameters constrained
S = 1.00	Δρ_max = 0.33 e Å⁻³
2941 reflections	Δρ_min = −0.32 e Å⁻³
218 parameters

Special details top

Geometry. Bond distances, angles etc. have been calculated using the rounded fractional coordinates. All su's are estimated from the variances of the (full) variance-covariance matrix. The cell e.s.d.'s are taken into account in the estimation of distances, angles and torsion angles

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	0.49246 (13)	0.08066 (10)	0.23725 (7)	0.0532 (4)
S1	0.86510 (13)	0.02559 (10)	0.15593 (7)	0.0428 (3)
F1	0.8027 (4)	0.4684 (3)	0.88468 (18)	0.0894 (11)
O1	1.0538 (3)	0.0163 (3)	0.19335 (18)	0.0532 (9)
O2	0.8416 (4)	0.1283 (3)	0.08580 (18)	0.0561 (10)
N1	0.7533 (4)	−0.1425 (3)	0.1110 (2)	0.0426 (10)
N2	0.7629 (4)	−0.0292 (3)	0.4293 (2)	0.0459 (11)
N3	0.7744 (4)	0.1263 (3)	0.4676 (2)	0.0483 (11)
C1	0.7272 (4)	−0.2167 (3)	0.2815 (3)	0.0336 (11)
C2	0.7020 (5)	−0.3359 (4)	0.3404 (3)	0.0450 (12)
C3	0.6839 (5)	−0.4857 (4)	0.2968 (3)	0.0516 (16)
C4	0.6917 (5)	−0.5215 (4)	0.1934 (3)	0.0523 (16)
C5	0.7157 (5)	−0.4082 (4)	0.1340 (3)	0.0478 (12)
C6	0.7322 (4)	−0.2558 (4)	0.1761 (3)	0.0365 (12)
C7	0.7362 (4)	0.0683 (4)	0.2675 (2)	0.0369 (12)
C8	0.7431 (4)	−0.0574 (3)	0.3326 (3)	0.0349 (11)
C9	0.7800 (5)	0.1472 (4)	0.5641 (3)	0.0460 (14)
C10	0.7926 (5)	0.2996 (4)	0.6232 (3)	0.0403 (12)
C11	0.7939 (5)	0.3134 (4)	0.7280 (3)	0.0446 (12)
C12	0.8044 (5)	0.4569 (5)	0.7816 (3)	0.0509 (14)
C13	0.8143 (5)	0.5861 (4)	0.7388 (3)	0.0555 (16)
C14	0.8139 (6)	0.5733 (5)	0.6347 (3)	0.0616 (17)
C15	0.8029 (5)	0.4312 (4)	0.5773 (3)	0.0520 (16)
C16	0.6640 (7)	−0.1733 (4)	0.0094 (3)	0.0738 (19)
H2	0.69751	−0.31273	0.41045	0.0537*
H3	0.66630	−0.56307	0.33701	0.0617*
H4	0.68056	−0.62314	0.16378	0.0630*
H5	0.72107	−0.43369	0.06412	0.0575*
H7	0.79712	0.16603	0.30513	0.0445*
H9	0.77593	0.06299	0.59809	0.0550*
H11	0.78773	0.22787	0.76088	0.0531*
H13	0.82112	0.68101	0.77869	0.0670*
H14	0.82110	0.66031	0.60328	0.0737*
H15	0.80241	0.42290	0.50700	0.0627*
H16A	0.73119	−0.24304	−0.03305	0.1104*
H16B	0.67065	−0.07948	−0.01841	0.1104*
H16C	0.53138	−0.21768	0.01300	0.1104*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Cl1	0.0468 (6)	0.0544 (6)	0.0638 (7)	0.0169 (5)	0.0014 (5)	0.0171 (5)
S1	0.0479 (6)	0.0375 (6)	0.0431 (6)	0.0047 (4)	0.0054 (4)	0.0072 (4)
F1	0.118 (2)	0.096 (2)	0.0487 (17)	0.0188 (16)	0.0047 (15)	−0.0117 (13)
O1	0.0366 (14)	0.0522 (16)	0.0688 (18)	0.0026 (12)	0.0021 (13)	0.0062 (14)
O2	0.0778 (19)	0.0452 (16)	0.0494 (17)	0.0094 (13)	0.0105 (14)	0.0197 (13)
N1	0.0589 (19)	0.0380 (18)	0.0290 (17)	0.0038 (14)	−0.0007 (14)	0.0021 (14)
N2	0.062 (2)	0.0408 (19)	0.0339 (19)	0.0118 (15)	−0.0019 (15)	−0.0016 (14)
N3	0.070 (2)	0.0406 (19)	0.0321 (19)	0.0104 (16)	−0.0009 (16)	−0.0043 (14)
C1	0.0342 (19)	0.031 (2)	0.035 (2)	0.0057 (15)	−0.0041 (16)	0.0025 (16)
C2	0.049 (2)	0.044 (2)	0.042 (2)	0.0071 (18)	−0.0016 (18)	0.0060 (19)
C3	0.059 (3)	0.038 (2)	0.059 (3)	0.0051 (19)	−0.007 (2)	0.014 (2)
C4	0.064 (3)	0.032 (2)	0.059 (3)	0.0044 (19)	−0.007 (2)	0.004 (2)
C5	0.057 (2)	0.044 (2)	0.040 (2)	0.0084 (19)	0.0006 (19)	−0.0031 (19)
C6	0.038 (2)	0.036 (2)	0.035 (2)	0.0062 (16)	−0.0027 (16)	0.0032 (17)
C7	0.040 (2)	0.034 (2)	0.034 (2)	0.0038 (16)	0.0010 (16)	−0.0024 (16)
C8	0.0325 (19)	0.035 (2)	0.036 (2)	0.0037 (15)	−0.0034 (16)	0.0025 (16)
C9	0.048 (2)	0.047 (2)	0.043 (3)	0.0120 (18)	0.0026 (19)	0.0019 (19)
C10	0.041 (2)	0.046 (2)	0.032 (2)	0.0069 (17)	0.0038 (16)	−0.0009 (18)
C11	0.049 (2)	0.047 (2)	0.036 (2)	0.0043 (18)	0.0045 (18)	0.0031 (18)
C12	0.054 (2)	0.066 (3)	0.027 (2)	0.006 (2)	0.0025 (18)	−0.010 (2)
C13	0.055 (3)	0.042 (2)	0.065 (3)	0.007 (2)	0.006 (2)	−0.008 (2)
C14	0.071 (3)	0.056 (3)	0.056 (3)	0.007 (2)	0.003 (2)	0.005 (2)
C15	0.062 (3)	0.053 (3)	0.039 (2)	0.006 (2)	0.0028 (19)	0.002 (2)
C16	0.123 (4)	0.056 (3)	0.039 (3)	0.002 (3)	−0.016 (3)	0.008 (2)

Geometric parameters (Å, º) top

Cl1—C7	1.774 (3)	C10—C11	1.386 (6)
S1—O1	1.427 (2)	C10—C15	1.395 (5)
S1—O2	1.426 (3)	C11—C12	1.369 (6)
S1—N1	1.620 (3)	C12—C13	1.353 (6)
S1—C7	1.772 (3)	C13—C14	1.377 (6)
F1—C12	1.365 (5)	C14—C15	1.378 (6)
N1—C6	1.418 (5)	C2—H2	0.9300
N1—C16	1.461 (5)	C3—H3	0.9300
N2—N3	1.402 (4)	C4—H4	0.9300
N2—C8	1.281 (5)	C5—H5	0.9300
N3—C9	1.274 (5)	C7—H7	0.9800
C1—C2	1.404 (5)	C9—H9	0.9300
C1—C6	1.402 (6)	C11—H11	0.9300
C1—C8	1.477 (4)	C13—H13	0.9300
C2—C3	1.370 (5)	C14—H14	0.9300
C3—C4	1.375 (6)	C15—H15	0.9300
C4—C5	1.365 (5)	C16—H16A	0.9600
C5—C6	1.386 (5)	C16—H16B	0.9600
C7—C8	1.521 (5)	C16—H16C	0.9600
C9—C10	1.464 (5)

O1—S1—O2	119.60 (17)	F1—C12—C13	118.7 (4)
O1—S1—N1	110.77 (16)	C11—C12—C13	124.2 (4)
O1—S1—C7	103.50 (14)	C12—C13—C14	118.3 (4)
O2—S1—N1	108.96 (15)	C13—C14—C15	119.8 (4)
O2—S1—C7	111.18 (16)	C10—C15—C14	120.9 (4)
N1—S1—C7	101.18 (15)	C1—C2—H2	119.00
S1—N1—C6	117.9 (2)	C3—C2—H2	119.00
S1—N1—C16	121.1 (2)	C2—C3—H3	120.00
C6—N1—C16	120.9 (3)	C4—C3—H3	120.00
N3—N2—C8	113.5 (3)	C3—C4—H4	120.00
N2—N3—C9	111.1 (3)	C5—C4—H4	120.00
C2—C1—C6	117.8 (3)	C4—C5—H5	119.00
C2—C1—C8	118.9 (3)	C6—C5—H5	119.00
C6—C1—C8	123.2 (3)	Cl1—C7—H7	109.00
C1—C2—C3	121.3 (4)	S1—C7—H7	109.00
C2—C3—C4	119.9 (3)	C8—C7—H7	109.00
C3—C4—C5	120.2 (3)	N3—C9—H9	119.00
C4—C5—C6	121.1 (4)	C10—C9—H9	119.00
N1—C6—C1	121.4 (3)	C10—C11—H11	121.00
N1—C6—C5	118.9 (3)	C12—C11—H11	121.00
C1—C6—C5	119.7 (3)	C12—C13—H13	121.00
Cl1—C7—S1	110.70 (15)	C14—C13—H13	121.00
Cl1—C7—C8	109.6 (2)	C13—C14—H14	120.00
S1—C7—C8	108.8 (2)	C15—C14—H14	120.00
N2—C8—C1	119.6 (3)	C10—C15—H15	120.00
N2—C8—C7	122.2 (3)	C14—C15—H15	120.00
C1—C8—C7	118.2 (3)	N1—C16—H16A	109.00
N3—C9—C10	122.1 (3)	N1—C16—H16B	109.00
C9—C10—C11	118.9 (3)	N1—C16—H16C	109.00
C9—C10—C15	122.0 (4)	H16A—C16—H16B	110.00
C11—C10—C15	119.0 (3)	H16A—C16—H16C	109.00
C10—C11—C12	117.9 (3)	H16B—C16—H16C	109.00
F1—C12—C11	117.2 (4)

O1—S1—N1—C6	56.5 (3)	C2—C1—C8—C7	−169.8 (3)
O2—S1—N1—C6	−170.0 (2)	C8—C1—C2—C3	179.1 (3)
C7—S1—N1—C6	−52.8 (3)	C6—C1—C2—C3	0.4 (5)
O1—S1—N1—C16	−128.2 (3)	C6—C1—C8—N2	−170.9 (3)
O2—S1—N1—C16	5.4 (3)	C1—C2—C3—C4	0.5 (5)
C7—S1—N1—C16	122.6 (3)	C2—C3—C4—C5	−0.6 (5)
N1—S1—C7—Cl1	−63.9 (2)	C3—C4—C5—C6	−0.1 (5)
O1—S1—C7—C8	−58.3 (2)	C4—C5—C6—N1	−178.8 (3)
O2—S1—C7—C8	172.1 (2)	C4—C5—C6—C1	1.0 (5)
N1—S1—C7—C8	56.5 (2)	Cl1—C7—C8—N2	−97.9 (3)
O1—S1—C7—Cl1	−178.68 (18)	Cl1—C7—C8—C1	82.4 (3)
O2—S1—C7—Cl1	51.7 (2)	S1—C7—C8—N2	141.0 (3)
C16—N1—C6—C5	31.8 (5)	S1—C7—C8—C1	−38.7 (3)
S1—N1—C6—C5	−152.9 (3)	N3—C9—C10—C11	178.6 (3)
S1—N1—C6—C1	27.3 (4)	N3—C9—C10—C15	−1.2 (5)
C16—N1—C6—C1	−148.0 (3)	C9—C10—C11—C12	−179.6 (3)
C8—N2—N3—C9	175.3 (3)	C15—C10—C11—C12	0.3 (5)
N3—N2—C8—C1	−179.5 (3)	C9—C10—C15—C14	179.7 (4)
N3—N2—C8—C7	0.9 (4)	C11—C10—C15—C14	−0.1 (5)
N2—N3—C9—C10	179.9 (3)	C10—C11—C12—F1	179.1 (3)
C2—C1—C6—N1	178.7 (3)	C10—C11—C12—C13	−0.3 (6)
C2—C1—C6—C5	−1.1 (4)	F1—C12—C13—C14	−179.3 (3)
C8—C1—C6—N1	0.0 (4)	C11—C12—C13—C14	0.0 (6)
C8—C1—C6—C5	−179.8 (3)	C12—C13—C14—C15	0.2 (6)
C6—C1—C8—C7	8.9 (4)	C13—C14—C15—C10	−0.2 (6)
C2—C1—C8—N2	10.5 (4)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C5—H5···F1ⁱ	0.93	2.53	3.442 (5)	167

Symmetry code: (i) x, y−1, z−1.

Experimental details

Crystal data
Chemical formula	C₁₆H₁₃ClFN₃O₂S
M_r	365.80
Crystal system, space group	Triclinic, P1
Temperature (K)	296
a, b, c (Å)	7.0072 (3), 8.9402 (4), 13.3438 (6)
α, β, γ (°)	98.184 (3), 90.510 (2), 98.389 (3)
V (Å³)	818.19 (6)
Z	2
Radiation type	Mo Kα
µ (mm⁻¹)	0.39
Crystal size (mm)	0.26 × 0.18 × 0.12

Data collection
Diffractometer	Bruker Kappa APEXII CCD diffractometer
Absorption correction	Multi-scan (SADABS; Bruker, 2005)
T_min, T_max	0.930, 0.960
No. of measured, independent and observed [I > 2σ(I)] reflections	11874, 2941, 1744
R_int	0.065
(sin θ/λ)_max (Å⁻¹)	0.600

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.050, 0.120, 1.00
No. of reflections	2941
No. of parameters	218
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.33, −0.32

Computer programs: APEX2 (Bruker, 2009), SAINT (Bruker, 2009), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), ORTEP-3 for Windows (Farrugia, 1997) and PLATON (Spek, 2009), WinGX (Farrugia, 1999) and PLATON (Spek, 2009).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C5—H5···F1ⁱ	0.93	2.53	3.442 (5)	167

Symmetry code: (i) x, y−1, z−1.

Acknowledgements

MS gratefully acknowledges the Higher Education Commission, Islamabad, Pakistan, for providing a scholarship under the Indigenous PhD Program (PIN 042–120567-PS2–276).

References

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