N-[4-(4-Fluoro­phen­yl)-1,3-thia­zol-2-yl]-3-(4-meth­oxy­phen­yl)-4-methyl­benzamide

Archana, K.; Lakshmithendral, K.; Saravanan, K.; Kabilan, S.; Selvanayagam, S.

doi:10.1107/S2414314617010896

organic compounds

IUCrDATA

ISSN: 2414-3146

Volume 2| Part 7| July 2017| x171089

https://doi.org/10.1107/S2414314617010896

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N-[4-(4-Fluorophenyl)-1,3-thiazol-2-yl]-3-(4-methoxyphenyl)-4-methylbenzamide

K. Archana,^a K. Lakshmithendral,^a K. Saravanan,^a S. Kabilan ^a ^* and S. Selvanayagam ^b ‡

^aDrug Discovery Lab, Department of Chemistry, Annamalai University, Annamalainagar, Chidambaram 608 002, India, and ^bPG & Research Department of Physics, Government Arts College, Melur 625 106, India
^*Correspondence e-mail: profskabilan@gmail.com

Edited by M. Bolte, Goethe-Universität Frankfurt, Germany (Received 22 July 2017; accepted 24 July 2017; online 28 July 2017)

In the title compound, C₂₄H₁₉FN₂O₂S, the dihedral angle between the fluorophenyl and thiazole rings is 12.8 (1)°. In the crystal, molecules are linked via strong N—H⋯O hydrogen bonds, forming C(11) chains propagating along [001]. In addition, C—H⋯O interactions are observed in this structure, forming C(10) chains propagating along [001].

Keywords: crystal structure; thiazole derivative; C—H⋯N intramolecular hydrogen bonds; N—H⋯O intermolecular hydrogen bonds; weak C—H⋯O interactions.

CCDC reference: 1564261

Structure description

In a continuation of our work on the crystal structure analysis of thiazole derivatives, we have undertaken a single-crystal X-ray diffraction study for the title compound, and the results are presented here.

The molecular structure of the title compound is illustrated in Fig. 1. The geometry of the present structure, except for atom F1, is comparable with that reported for a similar structure, namely 3-(4-methoxyphenyl)-4-methyl- N-[4-(4-methylphenyl)-1,3-thiazol-2-yl]benzamide (Archana et al., 2017 ). The superposition of the title compound with that in the above-mentioned structure, using Qmol (Gans & Shalloway, 2001 ), gives an r.m.s. deviation of 0.710 Å; see Fig. 2. The methoxy atoms O2 and C24 deviate by −0.014 (2) and 0.355 (3) Å, respectively from the ring to which they are attached. This ring is oriented at a dihedral angle of 82.2 (1)° with respect to the fluorophenyl ring. The fluorophenyl ring makes a dihedral angle of 12.8 (1)° with thiazole ring. The molecular structure is influenced by intramolecular C—H⋯N and C—H⋯O hydrogen bonds (Table 1).

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N2—H2A⋯O2ⁱ	0.86	2.33	3.177 (2)	167
C12—H12⋯O2ⁱ	0.93	2.36	3.275 (2)	167
C1—H1⋯N1	0.93	2.48	2.827 (3)	102
C16—H16⋯O1	0.93	2.49	2.802 (3)	100
Symmetry code: (i) $[x, -y+{\script{1\over 2}}, z-{\script{1\over 2}}]$ .

Figure 1
The molecular structure of the title compound, with atom labelling. Displacement ellipsoids are drawn at the 30% probability level.

Figure 2
Superposition of the present structure except F1 (yellow) with the similar reported structure (green; Archana et al., 2017

In the crystal, molecules are linked via strong N—H⋯O hydrogen bonds (Table 1), forming C(11) chains propagating along [001]. In addition, C—H⋯O interactions are observed in this structure, forming C(10) chains propagating along [001], see Fig. 3.

Figure 3
The crystal packing of the title compound viewed along b axis. The N—H⋯O and C—H⋯O intermolecular hydrogen bonds are shown as dashed lines (see Table 1

). For clarity, H atoms not involved in these hydrogen bonds have been omitted.

Synthesis and crystallization

N-(4-(4-Fluorophenyl) thiazol-2-yl)-3-iodo-4-methylbenzamide (0.23 mmol) was dissolved in 20 ml of deoxygenated toluene and water (8:2). Then, tetrakis (triphenylphosphine) palladium (0.014 mmol) and K₂CO₃ (0.68 mmol) were added in turn at 10 min intervals. Finally, 4-methoxy phenyl boronic acid (0.25 mmol) was added and the resulting reaction mixture was heated to reflux for 16 h under a nitrogen atmosphere. The progress of the reaction was monitored by pre-coated TLC plates. After completion of the reaction, it was cooled to rt and concentrated in Rotavac. The obtained crude compound was purified by column chromatography using 20% ethyl acetate and petrol ether (60–80) as eluent. The pure compound was obtained as a light-brown solid, it was further recrystallized from dichloromethane (DCM) solution to yield the title compound.

Refinement

Crystal data, data collection and structure refinement details are summarized in Table 2.

Table 2
Experimental details

Crystal data
Chemical formula	C₂₄H₁₉FN₂O₂S
M_r	418.47
Crystal system, space group	Monoclinic, P2₁/c
Temperature (K)	298
a, b, c (Å)	9.5104 (11), 10.4859 (13), 20.522 (3)
β (°)	94.904 (6)
V (Å³)	2039.1 (5)
Z	4
Radiation type	Mo Kα
μ (mm⁻¹)	0.19
Crystal size (mm)	0.24 × 0.21 × 0.19

Data collection
Diffractometer	Bruker SMART APEX CCD area-detector
No. of measured, independent and observed [I > 2σ(I)] reflections	9198, 4609, 3515
R_int	0.049
(sin θ/λ)_max (Å⁻¹)	0.649

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.055, 0.164, 1.04
No. of reflections	4609
No. of parameters	272
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.23, −0.29
Computer programs: SMART and SAINT (Bruker, 2002 ), SHELXS97 (Sheldrick, 2008 ), ORTEP-3 for Windows (Farrugia, 2012 ), SHELXL2014 (Sheldrick, 2015 ) and PLATON (Spek, 2009 ).

Structural data

CCDC reference: 1564261

Crystal structure: contains datablocks I, global. DOI: https://doi.org/10.1107/S2414314617010896/bt4058sup1.cif

Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S2414314617010896/bt4058Isup2.hkl

Supporting information file. DOI: https://doi.org/10.1107/S2414314617010896/bt4058Isup3.cml

checkCIF report

Computing details top

Data collection: SMART (Bruker, 2002); cell refinement: SAINT (Bruker, 2002); data reduction: SAINT (Bruker, 2002); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL2014 (Sheldrick, 2015); molecular graphics: ORTEP-3 for Windows (Farrugia, 2012) and PLATON (Spek, 2009); software used to prepare material for publication: SHELXL2014 (Sheldrick, 2015) and PLATON (Spek, 2009).

N-[4-(4-Fluorophenyl)-1,3-thiazol-2-yl]-3-(4-methoxyphenyl)-4-methylbenzamide top

Crystal data top

C₂₄H₁₉FN₂O₂S	F(000) = 872
M_r = 418.47	D_x = 1.363 Mg m⁻³
Monoclinic, P2₁/c	Mo Kα radiation, λ = 0.71073 Å
a = 9.5104 (11) Å	Cell parameters from 6448 reflections
b = 10.4859 (13) Å	θ = 3.2–27.4°
c = 20.522 (3) Å	µ = 0.19 mm⁻¹
β = 94.904 (6)°	T = 298 K
V = 2039.1 (5) Å³	Block, colourless
Z = 4	0.24 × 0.21 × 0.19 mm

Data collection top

Bruker SMART APEX CCD area-detector diffractometer	R_int = 0.049
Radiation source: fine-focus sealed tube	θ_max = 27.5°, θ_min = 3.0°
ω and φ scans	h = −11→12
9198 measured reflections	k = −13→11
4609 independent reflections	l = −26→11
3515 reflections with I > 2σ(I)

Refinement top

Refinement on F²	0 restraints
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F² > 2σ(F²)] = 0.055	H-atom parameters constrained
wR(F²) = 0.164	w = 1/[σ²(F_o²) + (0.0907P)² + 0.3443P] where P = (F_o² + 2F_c²)/3
S = 1.04	(Δ/σ)_max = 0.001
4609 reflections	Δρ_max = 0.23 e Å⁻³
272 parameters	Δρ_min = −0.29 e Å⁻³

Special details top

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.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å²) top

	x	y	z	U_iso*/U_eq
S1	0.36048 (6)	0.30153 (6)	0.39023 (3)	0.05611 (19)
O1	0.18520 (19)	0.2555 (2)	0.48536 (8)	0.0766 (6)
O2	−0.16903 (17)	−0.01682 (14)	0.82367 (6)	0.0525 (4)
N1	0.19087 (16)	0.41980 (15)	0.30669 (7)	0.0416 (4)
N2	0.08549 (18)	0.37141 (17)	0.40186 (8)	0.0465 (4)
H2A	0.0118	0.4130	0.3868	0.056*
F1	0.33315 (18)	0.56455 (18)	0.01917 (7)	0.0861 (5)
C1	0.2007 (2)	0.4880 (2)	0.17389 (10)	0.0492 (5)
H1	0.1152	0.4850	0.1927	0.059*
C2	0.2031 (2)	0.5264 (2)	0.10959 (11)	0.0561 (5)
H2	0.1202	0.5494	0.0851	0.067*
C3	0.3301 (2)	0.5299 (2)	0.08263 (10)	0.0557 (5)
C4	0.4533 (2)	0.4999 (2)	0.11726 (11)	0.0583 (6)
H4	0.5382	0.5049	0.0981	0.070*
C5	0.4504 (2)	0.4617 (2)	0.18184 (10)	0.0520 (5)
H5	0.5343	0.4408	0.2061	0.062*
C6	0.32380 (18)	0.45404 (18)	0.21081 (9)	0.0395 (4)
C7	0.31681 (19)	0.40683 (18)	0.27833 (9)	0.0410 (4)
C8	0.4196 (2)	0.3466 (2)	0.31653 (10)	0.0547 (5)
H8	0.5102	0.3316	0.3045	0.066*
C9	0.2002 (2)	0.36928 (18)	0.36480 (9)	0.0428 (4)
C10	0.0813 (2)	0.3116 (2)	0.46118 (10)	0.0496 (5)
C11	−0.0524 (2)	0.32029 (18)	0.49355 (9)	0.0436 (4)
C12	−0.1676 (2)	0.3939 (2)	0.47043 (10)	0.0518 (5)
H12	−0.1639	0.4416	0.4324	0.062*
C13	−0.2872 (2)	0.3962 (2)	0.50392 (10)	0.0524 (5)
H13	−0.3638	0.4449	0.4873	0.063*
C14	−0.2976 (2)	0.32849 (19)	0.56157 (9)	0.0444 (4)
C15	−0.1807 (2)	0.25463 (18)	0.58507 (8)	0.0404 (4)
C16	−0.0618 (2)	0.25063 (18)	0.55063 (9)	0.0430 (4)
H16	0.0140	0.1998	0.5661	0.052*
C17	−0.4322 (2)	0.3332 (2)	0.59434 (12)	0.0595 (6)
H17A	−0.4272	0.4008	0.6260	0.089*
H17B	−0.4459	0.2534	0.6159	0.089*
H17C	−0.5098	0.3483	0.5622	0.089*
C18	−0.18079 (19)	0.17911 (18)	0.64708 (8)	0.0398 (4)
C19	−0.1805 (2)	0.24186 (19)	0.70703 (9)	0.0496 (5)
H19	−0.1824	0.3305	0.7081	0.059*
C20	−0.1773 (2)	0.17391 (19)	0.76502 (9)	0.0482 (5)
H20	−0.1775	0.2168	0.8047	0.058*
C21	−0.17385 (19)	0.04177 (18)	0.76370 (8)	0.0396 (4)
C22	−0.17349 (19)	−0.02230 (18)	0.70483 (8)	0.0397 (4)
H22	−0.1709	−0.1109	0.7038	0.048*
C23	−0.17704 (18)	0.04781 (18)	0.64705 (8)	0.0384 (4)
H23	−0.1769	0.0048	0.6074	0.046*
C24	−0.2044 (3)	−0.1480 (2)	0.82531 (11)	0.0600 (6)
H24A	−0.1969	−0.1772	0.8698	0.090*
H24B	−0.2993	−0.1599	0.8064	0.090*
H24C	−0.1408	−0.1958	0.8008	0.090*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
S1	0.0566 (3)	0.0681 (4)	0.0430 (3)	0.0119 (3)	0.0002 (2)	0.0090 (2)
O1	0.0686 (10)	0.1041 (14)	0.0587 (10)	0.0258 (10)	0.0149 (8)	0.0362 (10)
O2	0.0802 (10)	0.0479 (8)	0.0281 (6)	−0.0105 (7)	−0.0029 (6)	0.0050 (5)
N1	0.0453 (8)	0.0451 (9)	0.0344 (7)	0.0006 (7)	0.0037 (6)	0.0028 (6)
N2	0.0504 (9)	0.0534 (10)	0.0361 (8)	0.0029 (7)	0.0056 (7)	0.0063 (7)
F1	0.0950 (11)	0.1105 (13)	0.0549 (8)	0.0169 (10)	0.0178 (8)	0.0380 (8)
C1	0.0434 (9)	0.0606 (13)	0.0440 (10)	0.0042 (9)	0.0064 (8)	0.0055 (9)
C2	0.0529 (11)	0.0652 (14)	0.0497 (11)	0.0070 (10)	0.0009 (9)	0.0141 (10)
C3	0.0696 (13)	0.0554 (13)	0.0428 (11)	0.0039 (11)	0.0093 (9)	0.0124 (9)
C4	0.0516 (11)	0.0688 (15)	0.0568 (13)	0.0012 (10)	0.0180 (10)	0.0143 (11)
C5	0.0421 (10)	0.0649 (13)	0.0492 (11)	0.0012 (9)	0.0049 (8)	0.0066 (10)
C6	0.0408 (9)	0.0375 (9)	0.0402 (9)	−0.0013 (7)	0.0034 (7)	−0.0023 (7)
C7	0.0423 (9)	0.0421 (10)	0.0385 (9)	−0.0013 (8)	0.0035 (7)	−0.0018 (7)
C8	0.0491 (11)	0.0695 (14)	0.0457 (11)	0.0081 (10)	0.0049 (9)	0.0028 (10)
C9	0.0499 (10)	0.0403 (10)	0.0381 (9)	−0.0004 (8)	0.0035 (8)	−0.0018 (7)
C10	0.0597 (12)	0.0510 (12)	0.0380 (10)	0.0026 (9)	0.0042 (8)	0.0067 (8)
C11	0.0533 (10)	0.0451 (11)	0.0321 (8)	−0.0003 (8)	0.0021 (7)	0.0029 (7)
C12	0.0641 (12)	0.0556 (12)	0.0352 (9)	0.0073 (10)	0.0015 (8)	0.0120 (8)
C13	0.0564 (11)	0.0571 (12)	0.0431 (10)	0.0106 (10)	0.0000 (9)	0.0122 (9)
C14	0.0515 (10)	0.0445 (10)	0.0369 (9)	−0.0001 (8)	0.0014 (8)	0.0029 (8)
C15	0.0511 (10)	0.0379 (9)	0.0314 (8)	−0.0026 (8)	−0.0008 (7)	0.0033 (7)
C16	0.0516 (10)	0.0439 (10)	0.0327 (8)	0.0005 (8)	−0.0008 (7)	0.0041 (7)
C17	0.0584 (12)	0.0648 (14)	0.0561 (12)	0.0081 (11)	0.0098 (10)	0.0142 (11)
C18	0.0435 (9)	0.0444 (10)	0.0314 (8)	−0.0010 (8)	0.0022 (7)	0.0035 (7)
C19	0.0737 (13)	0.0370 (10)	0.0371 (9)	−0.0016 (9)	−0.0005 (9)	0.0006 (7)
C20	0.0688 (13)	0.0436 (11)	0.0314 (8)	−0.0026 (9)	−0.0012 (8)	−0.0041 (7)
C21	0.0453 (9)	0.0435 (10)	0.0289 (8)	−0.0043 (8)	−0.0025 (7)	0.0027 (7)
C22	0.0474 (9)	0.0361 (9)	0.0349 (8)	−0.0032 (7)	−0.0005 (7)	0.0001 (7)
C23	0.0416 (9)	0.0441 (10)	0.0291 (8)	−0.0023 (7)	0.0006 (6)	−0.0025 (7)
C24	0.0842 (16)	0.0511 (12)	0.0440 (11)	−0.0103 (11)	0.0006 (10)	0.0115 (9)

Geometric parameters (Å, º) top

S1—C9	1.722 (2)	C11—C12	1.390 (3)
S1—C8	1.724 (2)	C12—C13	1.379 (3)
O1—C10	1.219 (3)	C12—H12	0.9300
O2—C21	1.373 (2)	C13—C14	1.391 (3)
O2—C24	1.417 (3)	C13—H13	0.9300
N1—C9	1.301 (2)	C14—C15	1.407 (3)
N1—C7	1.382 (2)	C14—C17	1.496 (3)
N2—C10	1.373 (2)	C15—C16	1.384 (3)
N2—C9	1.382 (2)	C15—C18	1.499 (2)
N2—H2A	0.8600	C16—H16	0.9300
F1—C3	1.355 (2)	C17—H17A	0.9600
C1—C2	1.381 (3)	C17—H17B	0.9600
C1—C6	1.386 (3)	C17—H17C	0.9600
C1—H1	0.9300	C18—C23	1.377 (3)
C2—C3	1.372 (3)	C18—C19	1.395 (3)
C2—H2	0.9300	C19—C20	1.385 (3)
C3—C4	1.354 (3)	C19—H19	0.9300
C4—C5	1.387 (3)	C20—C21	1.386 (3)
C4—H4	0.9300	C20—H20	0.9300
C5—C6	1.390 (3)	C21—C22	1.383 (2)
C5—H5	0.9300	C22—C23	1.393 (2)
C6—C7	1.478 (2)	C22—H22	0.9300
C7—C8	1.355 (3)	C23—H23	0.9300
C8—H8	0.9300	C24—H24A	0.9600
C10—C11	1.487 (3)	C24—H24B	0.9600
C11—C16	1.390 (2)	C24—H24C	0.9600

C9—S1—C8	88.13 (10)	C12—C13—C14	122.48 (19)
C21—O2—C24	117.77 (15)	C12—C13—H13	118.8
C9—N1—C7	110.62 (16)	C14—C13—H13	118.8
C10—N2—C9	124.37 (17)	C13—C14—C15	117.46 (18)
C10—N2—H2A	117.8	C13—C14—C17	119.44 (18)
C9—N2—H2A	117.8	C15—C14—C17	123.07 (17)
C2—C1—C6	121.00 (18)	C16—C15—C14	119.88 (16)
C2—C1—H1	119.5	C16—C15—C18	118.52 (16)
C6—C1—H1	119.5	C14—C15—C18	121.60 (17)
C3—C2—C1	118.71 (19)	C15—C16—C11	121.93 (18)
C3—C2—H2	120.6	C15—C16—H16	119.0
C1—C2—H2	120.6	C11—C16—H16	119.0
C4—C3—F1	118.6 (2)	C14—C17—H17A	109.5
C4—C3—C2	122.28 (19)	C14—C17—H17B	109.5
F1—C3—C2	119.2 (2)	H17A—C17—H17B	109.5
C3—C4—C5	118.80 (19)	C14—C17—H17C	109.5
C3—C4—H4	120.6	H17A—C17—H17C	109.5
C5—C4—H4	120.6	H17B—C17—H17C	109.5
C4—C5—C6	120.91 (19)	C23—C18—C19	118.28 (16)
C4—C5—H5	119.5	C23—C18—C15	121.73 (16)
C6—C5—H5	119.5	C19—C18—C15	119.96 (17)
C1—C6—C5	118.28 (18)	C20—C19—C18	120.89 (19)
C1—C6—C7	119.67 (17)	C20—C19—H19	119.6
C5—C6—C7	122.01 (17)	C18—C19—H19	119.6
C8—C7—N1	114.21 (17)	C19—C20—C21	119.74 (17)
C8—C7—C6	127.60 (17)	C19—C20—H20	120.1
N1—C7—C6	118.14 (16)	C21—C20—H20	120.1
C7—C8—S1	111.24 (16)	O2—C21—C22	124.30 (17)
C7—C8—H8	124.4	O2—C21—C20	115.38 (16)
S1—C8—H8	124.4	C22—C21—C20	120.31 (17)
N1—C9—N2	120.18 (17)	C21—C22—C23	119.05 (17)
N1—C9—S1	115.79 (14)	C21—C22—H22	120.5
N2—C9—S1	124.04 (14)	C23—C22—H22	120.5
O1—C10—N2	119.9 (2)	C18—C23—C22	121.73 (16)
O1—C10—C11	122.83 (18)	C18—C23—H23	119.1
N2—C10—C11	117.31 (18)	C22—C23—H23	119.1
C16—C11—C12	118.27 (18)	O2—C24—H24A	109.5
C16—C11—C10	117.63 (17)	O2—C24—H24B	109.5
C12—C11—C10	124.10 (17)	H24A—C24—H24B	109.5
C13—C12—C11	119.96 (18)	O2—C24—H24C	109.5
C13—C12—H12	120.0	H24A—C24—H24C	109.5
C11—C12—H12	120.0	H24B—C24—H24C	109.5

C6—C1—C2—C3	0.2 (4)	N2—C10—C11—C12	−5.9 (3)
C1—C2—C3—C4	−1.5 (4)	C16—C11—C12—C13	−0.1 (3)
C1—C2—C3—F1	178.5 (2)	C10—C11—C12—C13	−179.9 (2)
F1—C3—C4—C5	−178.6 (2)	C11—C12—C13—C14	1.1 (3)
C2—C3—C4—C5	1.4 (4)	C12—C13—C14—C15	−0.7 (3)
C3—C4—C5—C6	0.0 (4)	C12—C13—C14—C17	−178.6 (2)
C2—C1—C6—C5	1.1 (3)	C13—C14—C15—C16	−0.6 (3)
C2—C1—C6—C7	−176.7 (2)	C17—C14—C15—C16	177.2 (2)
C4—C5—C6—C1	−1.2 (3)	C13—C14—C15—C18	179.44 (18)
C4—C5—C6—C7	176.6 (2)	C17—C14—C15—C18	−2.8 (3)
C9—N1—C7—C8	−0.4 (2)	C14—C15—C16—C11	1.5 (3)
C9—N1—C7—C6	177.43 (17)	C18—C15—C16—C11	−178.51 (17)
C1—C6—C7—C8	165.9 (2)	C12—C11—C16—C15	−1.1 (3)
C5—C6—C7—C8	−11.8 (3)	C10—C11—C16—C15	178.59 (18)
C1—C6—C7—N1	−11.6 (3)	C16—C15—C18—C23	−66.0 (2)
C5—C6—C7—N1	170.67 (18)	C14—C15—C18—C23	114.0 (2)
N1—C7—C8—S1	0.8 (2)	C16—C15—C18—C19	112.1 (2)
C6—C7—C8—S1	−176.79 (16)	C14—C15—C18—C19	−68.0 (3)
C9—S1—C8—C7	−0.71 (18)	C23—C18—C19—C20	−0.4 (3)
C7—N1—C9—N2	−179.81 (16)	C15—C18—C19—C20	−178.49 (19)
C7—N1—C9—S1	−0.2 (2)	C18—C19—C20—C21	0.2 (3)
C10—N2—C9—N1	174.34 (19)	C24—O2—C21—C22	−18.0 (3)
C10—N2—C9—S1	−5.2 (3)	C24—O2—C21—C20	162.9 (2)
C8—S1—C9—N1	0.53 (17)	C19—C20—C21—O2	179.19 (19)
C8—S1—C9—N2	−179.87 (18)	C19—C20—C21—C22	0.0 (3)
C9—N2—C10—O1	2.6 (3)	O2—C21—C22—C23	−179.26 (17)
C9—N2—C10—C11	−178.13 (18)	C20—C21—C22—C23	−0.2 (3)
O1—C10—C11—C16	−6.4 (3)	C19—C18—C23—C22	0.2 (3)
N2—C10—C11—C16	174.37 (18)	C15—C18—C23—C22	178.31 (16)
O1—C10—C11—C12	173.4 (2)	C21—C22—C23—C18	0.1 (3)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N2—H2A···O2ⁱ	0.86	2.33	3.177 (2)	167
C12—H12···O2ⁱ	0.93	2.36	3.275 (2)	167
C1—H1···N1	0.93	2.48	2.827 (3)	102
C16—H16···O1	0.93	2.49	2.802 (3)	100

Symmetry code: (i) x, −y+1/2, z−1/2.

Footnotes

‡Additional correspondence author, e-mail: s_selvanayagam@rediffmail.com.

References

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