Crystal structure of 1-benzoyl-3-(4-fluoro­phen­yl)thio­urea

Jassas, R.S.; Asiri, A.M.; Arshad, M.N.; Zayed, M.E.M.; Mustafa, G.

doi:10.1107/S1600536814018376

organic compounds

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ISSN: 2056-9890

Volume 70| Part 9| September 2014| Pages o1023-o1024

doi:10.1107/S1600536814018376

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Crystal structure of 1-benzoyl-3-(4-fluorophenyl)thiourea

Rabab Sharaf Jassas,^a Abdullah M. Asiri,^a,^b Muhammad Nadeem Arshad,^a,^b ^* Mohie E. M. Zayed ^a and Ghulam Mustafa ^c ^*

^aChemistry Department, Faculty of Science, King Abdulaziz University, PO Box 80203, Jeddah 21589, Saudi Arabia, ^bCenter of Excellence for Advanced Materials Research (CEAMR), King Abdulaziz University, PO Box 80203, Jeddah 21589, Saudi Arabia, and ^cDepartment of Chemistry, University of Gujrat, Gujrat 50700, Pakistan
^*Correspondence e-mail: mnachemist@hotmail.com, ghulam.mustafa@uog.edu.pk

Edited by W. T. A. Harrison, University of Aberdeen, Scotland (Received 11 August 2014; accepted 12 August 2014; online 16 August 2014)

The title compound, C₁₄H₁₁FN₂OS, contains two molecules (A and B) in the asymmetric unit, with different conformations. In molecule A, the dihedral angles between the central thiourea grouping and the phenyl and fluorobenzene rings are 28.77 (8) and 41.82 (8)°, respectively, and the dihedral angle between the ring planes is 70.02 (9)°. Equivalent data for molecule B are 8.46 (8), 47.78 (8) and 52.99 (9)°, respectively. Both molecules feature an intramolecular N—H⋯O hydrogen bond, which closes an S(6) ring. In the crystal, A+B dimers linked by pairs of N—H⋯S hydrogen bonds generate R₂²(8) loops.

Keywords: crystal structure; thiourea; amide; hydrogen-bonded dimers.

CCDC reference: 1018979

1. Related literature

For related structures, see: Othman et al. (2010 ); Rauf et al. (2012 ) Saeed & Flörke (2006a , 2006b ); Saeed et al. (2011 ); Yamin & Yusof (2003a ,b ).

2. Experimental

2.1. Crystal data

C₁₄H₁₁FN₂OS
M_r = 274.31
Triclinic, $[P \overline 1]$
a = 9.6265 (4) Å
b = 11.1329 (4) Å
c = 13.8252 (5) Å
α = 110.646 (3)°
β = 100.708 (3)°
γ = 102.762 (3)°
V = 1294.58 (9) Å³
Z = 4
Cu Kα radiation
μ = 2.28 mm⁻¹
T = 296 K
0.36 × 0.28 × 0.22 mm

2.2. Data collection

Agilent SuperNova, Dual, Cu at zero, Atlas, CCD diffractometer
Absorption correction: multi-scan (CrysAlis PRO; Agilent, 2012 ) T_min = 0.817, T_max = 1.000
11636 measured reflections
5354 independent reflections
4757 reflections with I > 2σ(I)
R_int = 0.015

2.3. Refinement

R[F² > 2σ(F²)] = 0.036
wR(F²) = 0.102
S = 1.03
5354 reflections
346 parameters
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.20 e Å⁻³
Δρ_min = −0.35 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N2—H2⋯S2ⁱ	0.99	2.56	3.5433 (13)	170
N4—H4⋯S1ⁱ	0.93	2.74	3.5976 (13)	154
N1—H1⋯O1	0.86 (2)	1.95 (2)	2.6408 (17)	137.5 (19)
N3—H3⋯O2	0.98	1.81	2.6307 (17)	139
Symmetry code: (i) -x+1, -y+2, -z+1.

Data collection: CrysAlis PRO (Agilent, 2012); cell refinement: CrysAlis PRO; data reduction: CrysAlis PRO; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: PLATON (Spek, 2009 ); software used to prepare material for publication: WinGX (Farrugia, 2012 ) and X-SEED (Barbour, 2001 ).

Supporting information

CCDC reference: 1018979

Crystal structure: contains datablocks I, New_Global_Publ_Block. DOI: 10.1107/S1600536814018376/hb7271sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536814018376/hb7271Isup2.hkl

Supporting information file. DOI: 10.1107/S1600536814018376/hb7271Isup3.cml

checkCIF report

Synthesis and crystallization top

Benzoylisothiocyanate (1 g, 6.13 mmol) was dissolved in acetone (50 ml) and allowed to stirr for an hour. Then 4-flouroaniline(0.68 g, 6.13 mmol) was added to the above mixture and stirred for another 1 h. The completion of reaction was checked by thin layer chromatography (TLC). The mixture was poured into acidified water under stirring. The precipitate obtained were separated and washed with deionized cold distilled water and recrystallization from ethanol solution under slow evaporation method to produce colorless blocks of title compound.

Refinement top

All the aromatic C—H H-atoms were positioned with idealized geometry with C—H = 0.93 Å,for aromatic and refined as riding with U_iso(H) = 1.2U_eq(C). The N—H H-atoms were positioned in difference map and refined freely with N—H = 0.97 (4) Å, U_iso(H) = 1.2 for N atoms.

Related literature top

For related structures, see: Othman et al. (2010); Rauf et al. (2012) Saeed & Flörke (2006a, 2006b); Saeed et al. (2011); Yamin & Yusof (2003a,b).

Computing details top

Data collection: CrysAlis PRO (Agilent, 2012); cell refinement: CrysAlis PRO (Agilent, 2012); data reduction: CrysAlis PRO (Agilent, 2012); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: PLATON (Spek, 2009); software used to prepare material for publication: WinGX (Farrugia, 2012) and X-SEED (Barbour, 2001).

Figures top

	Fig. 1. The molecular structure of (I) with 50% displacement ellipsoids.
	Fig. 2. The inter and intramolecular hydrogen bonding shown using dashed lines.

1-Benzoyl-3-(4-fluorophenyl)thiourea top

Crystal data top

C₁₄H₁₁FN₂OS	V = 1294.58 (9) Å³
M_r = 274.31	Z = 4
Triclinic, P1	F(000) = 568
Hall symbol: -P 1	D_x = 1.407 Mg m⁻³
a = 9.6265 (4) Å	Cu Kα radiation, λ = 1.54184 Å
b = 11.1329 (4) Å	µ = 2.28 mm⁻¹
c = 13.8252 (5) Å	T = 296 K
α = 110.646 (3)°	Block, colorless
β = 100.708 (3)°	0.36 × 0.28 × 0.22 mm
γ = 102.762 (3)°

Data collection top

Agilent SuperNova, Dual, Cu at zero, Atlas, CCD diffractometer	5354 independent reflections
Radiation source: SuperNova (Cu) X-ray Source	4757 reflections with I > 2σ(I)
Mirror monochromator	R_int = 0.015
ω scans	θ_max = 76.5°, θ_min = 4.4°
Absorption correction: multi-scan (CrysAlis PRO; Agilent, 2012)	h = −12→11
T_min = 0.817, T_max = 1.000	k = −13→12
11636 measured reflections	l = −11→17

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)] = 0.036	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.102	H atoms treated by a mixture of independent and constrained refinement
S = 1.03	w = 1/[σ²(F_o²) + (0.0538P)² + 0.268P] where P = (F_o² + 2F_c²)/3
5354 reflections	(Δ/σ)_max = 0.001
346 parameters	Δρ_max = 0.20 e Å⁻³
0 restraints	Δρ_min = −0.35 e Å⁻³

Crystal data top

C₁₄H₁₁FN₂OS	γ = 102.762 (3)°
M_r = 274.31	V = 1294.58 (9) Å³
Triclinic, P1	Z = 4
a = 9.6265 (4) Å	Cu Kα radiation
b = 11.1329 (4) Å	µ = 2.28 mm⁻¹
c = 13.8252 (5) Å	T = 296 K
α = 110.646 (3)°	0.36 × 0.28 × 0.22 mm
β = 100.708 (3)°

Data collection top

Agilent SuperNova, Dual, Cu at zero, Atlas, CCD diffractometer	5354 independent reflections
Absorption correction: multi-scan (CrysAlis PRO; Agilent, 2012)	4757 reflections with I > 2σ(I)
T_min = 0.817, T_max = 1.000	R_int = 0.015
11636 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.036	0 restraints
wR(F²) = 0.102	H atoms treated by a mixture of independent and constrained refinement
S = 1.03	Δρ_max = 0.20 e Å⁻³
5354 reflections	Δρ_min = −0.35 e Å⁻³
346 parameters

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.

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
S1	0.10971 (5)	0.71506 (4)	0.58605 (3)	0.05533 (12)
S2	0.99550 (5)	1.23786 (4)	0.68544 (4)	0.06368 (14)
F1	0.42593 (15)	0.61882 (14)	1.00154 (8)	0.0807 (3)
F2	1.30145 (16)	1.00061 (14)	1.00287 (10)	0.0960 (4)
O1	0.30327 (17)	0.41067 (15)	0.38650 (9)	0.0768 (4)
O2	0.67259 (14)	0.81808 (11)	0.48289 (10)	0.0626 (3)
N1	0.28430 (16)	0.55698 (14)	0.57813 (10)	0.0533 (3)
N2	0.17580 (15)	0.56414 (13)	0.41761 (9)	0.0483 (3)
N3	0.91440 (14)	0.97471 (12)	0.64274 (10)	0.0513 (3)
N4	0.78454 (14)	1.03902 (13)	0.52148 (10)	0.0504 (3)
C1	0.19583 (17)	0.60743 (14)	0.52881 (11)	0.0454 (3)
C2	0.31803 (16)	0.57760 (15)	0.68871 (11)	0.0456 (3)
C3	0.3556 (2)	0.70415 (16)	0.77249 (13)	0.0559 (4)
H3A	0.3568	0.7797	0.7578	0.067*
C4	0.39115 (19)	0.71680 (17)	0.87823 (12)	0.0586 (4)
H4A	0.4153	0.8006	0.9354	0.070*
C5	0.39026 (18)	0.60464 (18)	0.89724 (12)	0.0543 (4)
C6	0.3546 (2)	0.47939 (18)	0.81661 (14)	0.0583 (4)
H6	0.3548	0.4046	0.8321	0.070*
C7	0.31813 (18)	0.46637 (16)	0.71082 (12)	0.0526 (3)
H7	0.2935	0.3819	0.6544	0.063*
C8	0.22178 (18)	0.46495 (16)	0.35187 (12)	0.0505 (3)
C9	0.16680 (16)	0.42877 (14)	0.23398 (11)	0.0438 (3)
C10	0.02856 (17)	0.43219 (15)	0.18570 (12)	0.0475 (3)
H10	−0.0331	0.4603	0.2274	0.057*
C11	−0.01708 (19)	0.39336 (17)	0.07491 (13)	0.0549 (4)
H11	−0.1100	0.3949	0.0423	0.066*
C12	0.0745 (2)	0.35248 (17)	0.01270 (12)	0.0571 (4)
H12	0.0438	0.3275	−0.0614	0.069*
C13	0.2114 (2)	0.34884 (18)	0.06075 (13)	0.0585 (4)
H13	0.2733	0.3216	0.0189	0.070*
C14	0.25746 (18)	0.38540 (16)	0.17091 (12)	0.0524 (3)
H14	0.3491	0.3809	0.2027	0.063*
C15	0.89789 (16)	1.07566 (15)	0.61595 (12)	0.0466 (3)
C16	1.01650 (17)	0.98710 (14)	0.73730 (12)	0.0470 (3)
C17	1.16625 (18)	1.05699 (17)	0.76648 (13)	0.0541 (4)
H17	1.2019	1.1011	0.7259	0.065*
C18	1.2625 (2)	1.06121 (19)	0.85570 (15)	0.0637 (4)
H18	1.3633	1.1082	0.8761	0.076*
C19	1.2071 (2)	0.99480 (18)	0.91389 (14)	0.0635 (4)
C20	1.0604 (2)	0.92345 (18)	0.88583 (16)	0.0668 (5)
H20	1.0258	0.8785	0.9262	0.080*
C21	0.9641 (2)	0.91938 (16)	0.79610 (15)	0.0584 (4)
H21	0.8638	0.8708	0.7754	0.070*
C22	0.67355 (17)	0.91742 (15)	0.46324 (12)	0.0482 (3)
C23	0.55378 (16)	0.91245 (15)	0.37529 (12)	0.0475 (3)
C24	0.53131 (18)	1.02572 (19)	0.36376 (15)	0.0609 (4)
H24	0.5928	1.1114	0.4126	0.073*
C25	0.4163 (2)	1.0108 (2)	0.27875 (18)	0.0735 (5)
H25	0.4017	1.0869	0.2705	0.088*
C26	0.3241 (2)	0.8846 (2)	0.20673 (16)	0.0721 (5)
H26	0.2483	0.8755	0.1495	0.086*
C27	0.3438 (2)	0.7719 (2)	0.21907 (15)	0.0713 (5)
H27	0.2803	0.6866	0.1709	0.086*
C28	0.45776 (19)	0.78475 (18)	0.30293 (14)	0.0610 (4)
H28	0.4705	0.7082	0.3112	0.073*
H2	0.1172	0.6095	0.3842	0.073*
H4	0.7819	1.1067	0.4974	0.073*
H3	0.8390	0.8878	0.5964	0.073*
H1	0.316 (2)	0.497 (2)	0.5386 (17)	0.073*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
S1	0.0705 (3)	0.0524 (2)	0.0459 (2)	0.02927 (18)	0.02121 (17)	0.01513 (16)
S2	0.0710 (3)	0.0427 (2)	0.0561 (2)	0.00407 (18)	−0.00598 (19)	0.01671 (17)
F1	0.0990 (8)	0.1050 (9)	0.0398 (5)	0.0368 (7)	0.0174 (5)	0.0300 (5)
F2	0.1099 (10)	0.0882 (9)	0.0716 (7)	0.0323 (7)	−0.0158 (7)	0.0321 (7)
O1	0.1027 (10)	0.0990 (10)	0.0416 (6)	0.0699 (9)	0.0178 (6)	0.0220 (6)
O2	0.0697 (7)	0.0427 (6)	0.0563 (7)	0.0099 (5)	−0.0017 (5)	0.0133 (5)
N1	0.0669 (8)	0.0583 (8)	0.0355 (6)	0.0310 (7)	0.0137 (6)	0.0137 (5)
N2	0.0616 (7)	0.0484 (7)	0.0353 (6)	0.0238 (6)	0.0130 (5)	0.0140 (5)
N3	0.0537 (7)	0.0411 (6)	0.0465 (7)	0.0127 (5)	0.0024 (5)	0.0112 (5)
N4	0.0534 (7)	0.0444 (6)	0.0437 (6)	0.0091 (5)	0.0043 (5)	0.0158 (5)
C1	0.0529 (8)	0.0406 (7)	0.0372 (7)	0.0126 (6)	0.0117 (6)	0.0118 (5)
C2	0.0477 (7)	0.0486 (8)	0.0357 (7)	0.0153 (6)	0.0101 (6)	0.0125 (6)
C3	0.0672 (10)	0.0456 (8)	0.0446 (8)	0.0137 (7)	0.0086 (7)	0.0131 (6)
C4	0.0646 (10)	0.0559 (9)	0.0372 (7)	0.0166 (7)	0.0060 (7)	0.0045 (6)
C5	0.0535 (8)	0.0705 (10)	0.0363 (7)	0.0190 (7)	0.0121 (6)	0.0194 (7)
C6	0.0665 (10)	0.0565 (9)	0.0523 (9)	0.0174 (8)	0.0129 (7)	0.0260 (7)
C7	0.0610 (9)	0.0454 (8)	0.0419 (7)	0.0172 (7)	0.0091 (6)	0.0098 (6)
C8	0.0583 (9)	0.0552 (8)	0.0385 (7)	0.0255 (7)	0.0136 (6)	0.0152 (6)
C9	0.0513 (7)	0.0404 (7)	0.0373 (7)	0.0153 (6)	0.0124 (6)	0.0130 (5)
C10	0.0515 (8)	0.0466 (7)	0.0440 (7)	0.0179 (6)	0.0142 (6)	0.0163 (6)
C11	0.0580 (9)	0.0562 (9)	0.0472 (8)	0.0172 (7)	0.0067 (7)	0.0220 (7)
C12	0.0724 (10)	0.0552 (9)	0.0378 (7)	0.0145 (8)	0.0122 (7)	0.0174 (7)
C13	0.0662 (10)	0.0641 (10)	0.0443 (8)	0.0213 (8)	0.0246 (7)	0.0162 (7)
C14	0.0520 (8)	0.0582 (9)	0.0449 (8)	0.0206 (7)	0.0148 (6)	0.0164 (7)
C15	0.0488 (7)	0.0439 (7)	0.0411 (7)	0.0128 (6)	0.0100 (6)	0.0130 (6)
C16	0.0516 (8)	0.0388 (7)	0.0444 (7)	0.0181 (6)	0.0095 (6)	0.0100 (6)
C17	0.0512 (8)	0.0591 (9)	0.0493 (8)	0.0194 (7)	0.0151 (7)	0.0177 (7)
C18	0.0534 (9)	0.0623 (10)	0.0594 (10)	0.0188 (8)	0.0046 (7)	0.0125 (8)
C19	0.0767 (11)	0.0530 (9)	0.0506 (9)	0.0284 (8)	−0.0005 (8)	0.0143 (7)
C20	0.0863 (13)	0.0541 (9)	0.0666 (11)	0.0264 (9)	0.0169 (9)	0.0322 (8)
C21	0.0587 (9)	0.0454 (8)	0.0697 (10)	0.0152 (7)	0.0107 (8)	0.0268 (7)
C22	0.0510 (8)	0.0445 (7)	0.0404 (7)	0.0131 (6)	0.0115 (6)	0.0096 (6)
C23	0.0444 (7)	0.0531 (8)	0.0406 (7)	0.0131 (6)	0.0142 (6)	0.0143 (6)
C24	0.0480 (8)	0.0605 (10)	0.0698 (11)	0.0093 (7)	0.0105 (7)	0.0298 (8)
C25	0.0551 (10)	0.0889 (14)	0.0904 (14)	0.0205 (9)	0.0156 (9)	0.0564 (12)
C26	0.0524 (9)	0.1022 (15)	0.0569 (10)	0.0162 (10)	0.0074 (8)	0.0364 (10)
C27	0.0607 (10)	0.0747 (12)	0.0524 (10)	0.0125 (9)	0.0015 (8)	0.0093 (9)
C28	0.0578 (9)	0.0569 (9)	0.0507 (9)	0.0143 (7)	0.0055 (7)	0.0093 (7)

Geometric parameters (Å, º) top

S1—C1	1.6623 (15)	C10—C11	1.388 (2)
S2—C15	1.6608 (15)	C10—H10	0.9300
F1—C5	1.3616 (17)	C11—C12	1.381 (2)
F2—C19	1.3585 (19)	C11—H11	0.9300
O1—C8	1.2181 (19)	C12—C13	1.377 (2)
O2—C22	1.2269 (19)	C12—H12	0.9300
N1—C1	1.3309 (19)	C13—C14	1.383 (2)
N1—C2	1.4250 (18)	C13—H13	0.9300
N1—H1	0.86 (2)	C14—H14	0.9300
N2—C8	1.3781 (19)	C16—C21	1.379 (2)
N2—C1	1.3998 (18)	C16—C17	1.383 (2)
N2—H2	0.9905	C17—C18	1.378 (2)
N3—C15	1.3327 (19)	C17—H17	0.9300
N3—C16	1.4246 (19)	C18—C19	1.372 (3)
N3—H3	0.9761	C18—H18	0.9300
N4—C22	1.3767 (19)	C19—C20	1.364 (3)
N4—C15	1.4004 (19)	C20—C21	1.384 (2)
N4—H4	0.9287	C20—H20	0.9300
C2—C7	1.376 (2)	C21—H21	0.9300
C2—C3	1.388 (2)	C22—C23	1.488 (2)
C3—C4	1.386 (2)	C23—C24	1.383 (2)
C3—H3A	0.9300	C23—C28	1.396 (2)
C4—C5	1.362 (2)	C24—C25	1.390 (3)
C4—H4A	0.9300	C24—H24	0.9300
C5—C6	1.362 (2)	C25—C26	1.374 (3)
C6—C7	1.386 (2)	C25—H25	0.9300
C6—H6	0.9300	C26—C27	1.372 (3)
C7—H7	0.9300	C26—H26	0.9300
C8—C9	1.4904 (19)	C27—C28	1.382 (2)
C9—C14	1.388 (2)	C27—H27	0.9300
C9—C10	1.389 (2)	C28—H28	0.9300

C1—N1—C2	127.39 (13)	C12—C13—C14	120.38 (15)
C1—N1—H1	117.5 (14)	C12—C13—H13	119.8
C2—N1—H1	114.6 (14)	C14—C13—H13	119.8
C8—N2—C1	127.90 (12)	C13—C14—C9	119.97 (15)
C8—N2—H2	118.4	C13—C14—H14	120.0
C1—N2—H2	113.6	C9—C14—H14	120.0
C15—N3—C16	126.08 (12)	N3—C15—N4	115.58 (13)
C15—N3—H3	114.0	N3—C15—S2	126.05 (11)
C16—N3—H3	119.4	N4—C15—S2	118.34 (11)
C22—N4—C15	127.94 (13)	C21—C16—C17	120.04 (15)
C22—N4—H4	116.5	C21—C16—N3	118.07 (14)
C15—N4—H4	115.5	C17—C16—N3	121.74 (14)
N1—C1—N2	115.29 (13)	C18—C17—C16	119.95 (16)
N1—C1—S1	126.60 (11)	C18—C17—H17	120.0
N2—C1—S1	118.10 (11)	C16—C17—H17	120.0
C7—C2—C3	120.12 (14)	C19—C18—C17	118.83 (17)
C7—C2—N1	117.19 (13)	C19—C18—H18	120.6
C3—C2—N1	122.63 (14)	C17—C18—H18	120.6
C4—C3—C2	119.32 (15)	F2—C19—C20	118.72 (18)
C4—C3—H3A	120.3	F2—C19—C18	118.92 (18)
C2—C3—H3A	120.3	C20—C19—C18	122.36 (16)
C5—C4—C3	119.02 (15)	C19—C20—C21	118.61 (17)
C5—C4—H4A	120.5	C19—C20—H20	120.7
C3—C4—H4A	120.5	C21—C20—H20	120.7
F1—C5—C6	118.81 (16)	C16—C21—C20	120.20 (17)
F1—C5—C4	118.31 (15)	C16—C21—H21	119.9
C6—C5—C4	122.88 (15)	C20—C21—H21	119.9
C5—C6—C7	118.19 (15)	O2—C22—N4	121.91 (14)
C5—C6—H6	120.9	O2—C22—C23	121.47 (14)
C7—C6—H6	120.9	N4—C22—C23	116.62 (13)
C2—C7—C6	120.45 (14)	C24—C23—C28	119.36 (15)
C2—C7—H7	119.8	C24—C23—C22	123.87 (14)
C6—C7—H7	119.8	C28—C23—C22	116.76 (14)
O1—C8—N2	123.06 (13)	C23—C24—C25	119.67 (17)
O1—C8—C9	121.47 (13)	C23—C24—H24	120.2
N2—C8—C9	115.47 (13)	C25—C24—H24	120.2
C14—C9—C10	119.75 (13)	C26—C25—C24	120.52 (19)
C14—C9—C8	117.40 (13)	C26—C25—H25	119.7
C10—C9—C8	122.81 (13)	C24—C25—H25	119.7
C11—C10—C9	119.64 (14)	C27—C26—C25	120.09 (18)
C11—C10—H10	120.2	C27—C26—H26	120.0
C9—C10—H10	120.2	C25—C26—H26	120.0
C12—C11—C10	120.43 (15)	C26—C27—C28	120.17 (18)
C12—C11—H11	119.8	C26—C27—H27	119.9
C10—C11—H11	119.8	C28—C27—H27	119.9
C13—C12—C11	119.81 (14)	C27—C28—C23	120.16 (18)
C13—C12—H12	120.1	C27—C28—H28	119.9
C11—C12—H12	120.1	C23—C28—H28	119.9

C2—N1—C1—N2	−176.44 (14)	C16—N3—C15—N4	−176.80 (14)
C2—N1—C1—S1	3.8 (2)	C16—N3—C15—S2	1.6 (2)
C8—N2—C1—N1	8.3 (2)	C22—N4—C15—N3	11.7 (2)
C8—N2—C1—S1	−171.98 (13)	C22—N4—C15—S2	−166.79 (13)
C1—N1—C2—C7	136.52 (17)	C15—N3—C16—C21	132.89 (17)
C1—N1—C2—C3	−46.1 (2)	C15—N3—C16—C17	−51.5 (2)
C7—C2—C3—C4	−0.8 (3)	C21—C16—C17—C18	−1.3 (2)
N1—C2—C3—C4	−178.15 (15)	N3—C16—C17—C18	−176.91 (14)
C2—C3—C4—C5	0.9 (3)	C16—C17—C18—C19	0.3 (3)
C3—C4—C5—F1	179.79 (15)	C17—C18—C19—F2	−178.97 (16)
C3—C4—C5—C6	−0.5 (3)	C17—C18—C19—C20	0.8 (3)
F1—C5—C6—C7	179.82 (15)	F2—C19—C20—C21	179.03 (16)
C4—C5—C6—C7	0.2 (3)	C18—C19—C20—C21	−0.7 (3)
C3—C2—C7—C6	0.4 (2)	C17—C16—C21—C20	1.4 (2)
N1—C2—C7—C6	177.91 (15)	N3—C16—C21—C20	177.13 (15)
C5—C6—C7—C2	−0.1 (3)	C19—C20—C21—C16	−0.4 (3)
C1—N2—C8—O1	−8.6 (3)	C15—N4—C22—O2	−8.8 (3)
C1—N2—C8—C9	172.24 (14)	C15—N4—C22—C23	170.92 (14)
O1—C8—C9—C14	−29.9 (2)	O2—C22—C23—C24	165.86 (16)
N2—C8—C9—C14	149.29 (15)	N4—C22—C23—C24	−13.8 (2)
O1—C8—C9—C10	147.74 (18)	O2—C22—C23—C28	−12.5 (2)
N2—C8—C9—C10	−33.1 (2)	N4—C22—C23—C28	167.86 (14)
C14—C9—C10—C11	−0.6 (2)	C28—C23—C24—C25	−1.8 (3)
C8—C9—C10—C11	−178.13 (14)	C22—C23—C24—C25	179.94 (16)
C9—C10—C11—C12	−0.5 (2)	C23—C24—C25—C26	0.6 (3)
C10—C11—C12—C13	0.7 (3)	C24—C25—C26—C27	0.8 (3)
C11—C12—C13—C14	0.3 (3)	C25—C26—C27—C28	−1.0 (3)
C12—C13—C14—C9	−1.4 (3)	C26—C27—C28—C23	−0.3 (3)
C10—C9—C14—C13	1.5 (2)	C24—C23—C28—C27	1.6 (3)
C8—C9—C14—C13	179.19 (15)	C22—C23—C28—C27	−179.96 (16)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N2—H2···S2ⁱ	0.99	2.56	3.5433 (13)	170
N4—H4···S1ⁱ	0.93	2.74	3.5976 (13)	154
N1—H1···O1	0.86 (2)	1.95 (2)	2.6408 (17)	137.5 (19)
N3—H3···O2	0.98	1.81	2.6307 (17)	139

Symmetry code: (i) −x+1, −y+2, −z+1.

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N2—H2···S2ⁱ	0.99	2.56	3.5433 (13)	170.3
N4—H4···S1ⁱ	0.93	2.74	3.5976 (13)	154.2
N1—H1···O1	0.86 (2)	1.95 (2)	2.6408 (17)	137.5 (19)
N3—H3···O2	0.98	1.81	2.6307 (17)	139.2

Symmetry code: (i) −x+1, −y+2, −z+1.

Acknowledgements

This paper was funded by King Abdulaziz University, under grant No. (T-001/431). The authors, therefore, acknowledge technical and financial support of KAU.

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Volume 70| Part 9| September 2014| Pages o1023-o1024

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