Crystal structure of 4-fluoro-N-[2-(4-fluoro­benzo­yl)hydra­zine-1-carbono­thio­yl]benzamide

Firdausiah, S.; Salleh Huddin, A.A.; Hasbullah, S.A.; Yamin, B.M.; Yusoff, S.F.M.

doi:10.1107/S1600536814015761

organic compounds

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ISSN: 2056-9890

Volume 70| Part 9| September 2014| Pages o915-o916

doi:10.1107/S1600536814015761

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Crystal structure of 4-fluoro-N-[2-(4-fluorobenzoyl)hydrazine-1-carbonothioyl]benzamide

Syadza Firdausiah,^a Ameera Aqeela Salleh Huddin,^a Siti Aishah Hasbullah,^a Bohari M. Yamin ^a and Siti Fairus M. Yusoff ^a ^*

^aSchool of Chemical Sciences and Food Technology, Universiti Kebangsaan Malaysia, 43600 Bangi, Selangor, Malaysia
^*Correspondence e-mail: sitifairus@ukm.edu.my

Edited by W. T. A. Harrison, University of Aberdeen, Scotland (Received 2 July 2014; accepted 6 July 2014; online 1 August 2014)

In the title compound, C₁₅H₁₁F₂N₃O₂S, the dihedral angle between the fluorobenzene rings is 88.43 (10)° and that between the central semithiocarbazide grouping is 47.00 (11)°. The dihedral angle between the amide group and attached fluorobenzene ring is 50.52 (11)°; the equivalent angle between the carbonylthioamide group and its attached ring is 12.98 (10)°. The major twists in the molecule occur about the C—N—N—C bonds [torsion angle = −138.7 (2)°] and the C_ar—C_ar—C—N (ar = aromatic) bonds [−132.0 (2)°]. An intramolecular N—H⋯O hydrogen bond occurs, which generates an S(6) ring. In the crystal, the molecules are linked by N—H⋯O and N—H⋯S hydrogen bonds, generating (001) sheets. Weak C—H⋯O and C—H⋯F interactions are also observed.

Keywords: crystal structure; hydrogen bonds; semithiocarbazide.

CCDC reference: 1012471

1. Related literature

For further synthetic details and the crystal structures of related thiourea derivatives, see: Yamin & Yusof (2003a ,b ); Yusof et al. (2003 ); For a metal complex with a similar ligand, see: Ke et al. (2007 ).

2. Experimental

2.1. Crystal data

C₁₅H₁₁F₂N₃O₂S
M_r = 335.33
Orthorhombic, P b c a
a = 11.6172 (6) Å
b = 8.4086 (5) Å
c = 30.0002 (16) Å
V = 2930.6 (3) Å³
Z = 8
Mo Kα radiation
μ = 0.26 mm⁻¹
T = 296 K
0.50 × 0.12 × 0.08 mm

2.2. Data collection

Bruker SMART APEX CCD diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2000 ) T_min = 0.883, T_max = 0.980
76830 measured reflections
2886 independent reflections
2024 reflections with I > 2σ(I)
R_int = 0.137

2.3. Refinement

R[F² > 2σ(F²)] = 0.046
wR(F²) = 0.099
S = 1.04
2886 reflections
208 parameters
H-atom parameters constrained
Δρ_max = 0.27 e Å⁻³
Δρ_min = −0.21 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N2—H2A⋯O1	0.86	1.89	2.571 (2)	135
N2—H2A⋯S1ⁱ	0.86	2.84	3.3875 (18)	123
N1—H1A⋯O2ⁱⁱ	0.86	2.33	3.165 (2)	165
N3—H3⋯O2ⁱⁱⁱ	0.86	2.10	2.942 (2)	166
C4—H4⋯F1^iv	0.93	2.49	3.409 (3)	169
C5—H5⋯O2ⁱⁱ	0.93	2.45	3.345 (3)	160
Symmetry codes: (i) $[x-{\script{1\over 2}}, y, -z+{\script{3\over 2}}]$ ; (ii) $[x+{\script{1\over 2}}, y, -z+{\script{3\over 2}}]$ ; (iii) $[-x+{\script{3\over 2}}, y-{\script{1\over 2}}, z]$ ; (iv) -x+2, -y+1, -z+2.

Data collection: SMART (Bruker, 2000); cell refinement: SAINT (Bruker, 2000); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXTL and PLATON (Spek, 2009 ).

Supporting information

CCDC reference: 1012471

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536814015761/hb7245sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536814015761/hb7245Isup2.hkl

checkCIF report

Related literature top

For further synthetic details and the crystal structures of related thiourea derivatives, see: Yamin & Yusof (2003a,b); Yusof et al. (2003); For a metal complex with a similar ligand, see: Ke et al. (2007).

Experimental top

30 ml acetone containing 4-fluorobenzoyl isothiocyanate (1.81 g, 0.01 mol) was mixed with hydrazine (0.16 g, 0.005 mol). The mixture was refluxed for 2 hours. The solution was filtered and left to evaporate at room temperature. The white precipitate obtained after a few days, was washed with water and cold ethanol. Colourless blocks of the title compound were obtained by recrystallization from ethanol solution.

Computing details top

Data collection: SMART (Bruker, 2000); cell refinement: SAINT (Bruker, 2000); data reduction: SAINT (Bruker, 2000); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (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. : Molecular structure of (I) with 50% probability displacement ellipsoids. The dashes line indicates the intramolecular hydrogen bond.
	Fig. 2. : Unit-cell packing for (I) in the unit cell viewed down a axis. The dashes lines indicate hydrogen bonds.

4-Fluoro-N-[2-(4-fluorobenzoyl)hydrazine-1-carbonothioyl]benzamide top

Crystal data top

C₁₅H₁₁F₂N₃O₂S	Z = 8
M_r = 335.33	F(000) = 1376
Orthorhombic, Pbca	D_x = 1.520 Mg m⁻³
Hall symbol: -P 2ac 2ab	Mo Kα radiation, λ = 0.71073 Å
a = 11.6172 (6) Å	µ = 0.26 mm⁻¹
b = 8.4086 (5) Å	T = 296 K
c = 30.0002 (16) Å	Block, colorless
V = 2930.6 (3) Å³	0.50 × 0.12 × 0.08 mm

Data collection top

Bruker SMART APEX CCD diffractometer	2886 independent reflections
Radiation source: fine-focus sealed tube	2024 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.137
ω scans	θ_max = 26.0°, θ_min = 3.1°
Absorption correction: multi-scan (SADABS; Bruker, 2000)	h = −14→14
T_min = 0.883, T_max = 0.980	k = −10→10
76830 measured reflections	l = −37→37

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)] = 0.046	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.099	H-atom parameters constrained
S = 1.04	w = 1/[σ²(F_o²) + (0.0354P)² + 2.0394P] where P = (F_o² + 2F_c²)/3
2886 reflections	(Δ/σ)_max = 0.001
208 parameters	Δρ_max = 0.27 e Å⁻³
0 restraints	Δρ_min = −0.21 e Å⁻³

Crystal data top

C₁₅H₁₁F₂N₃O₂S	V = 2930.6 (3) Å³
M_r = 335.33	Z = 8
Orthorhombic, Pbca	Mo Kα radiation
a = 11.6172 (6) Å	µ = 0.26 mm⁻¹
b = 8.4086 (5) Å	T = 296 K
c = 30.0002 (16) Å	0.50 × 0.12 × 0.08 mm

Data collection top

Bruker SMART APEX CCD diffractometer	2886 independent reflections
Absorption correction: multi-scan (SADABS; Bruker, 2000)	2024 reflections with I > 2σ(I)
T_min = 0.883, T_max = 0.980	R_int = 0.137
76830 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.046	0 restraints
wR(F²) = 0.099	H-atom parameters constrained
S = 1.04	Δρ_max = 0.27 e Å⁻³
2886 reflections	Δρ_min = −0.21 e Å⁻³
208 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	0.98887 (5)	0.15863 (8)	0.73680 (2)	0.04054 (19)
O1	0.69608 (15)	0.4074 (2)	0.80598 (6)	0.0585 (6)
O2	0.64343 (13)	0.34844 (18)	0.67414 (5)	0.0328 (4)
N1	0.88035 (15)	0.3239 (2)	0.79937 (6)	0.0283 (4)
H1A	0.9472	0.3290	0.8116	0.034*
N2	0.76928 (15)	0.2357 (2)	0.74100 (6)	0.0308 (5)
H2A	0.7137	0.2871	0.7533	0.037*
N3	0.74823 (15)	0.1473 (2)	0.70307 (5)	0.0278 (4)
H3	0.7784	0.0548	0.6995	0.033*
C1	0.7245 (2)	0.5302 (3)	0.88928 (8)	0.0444 (7)
H1	0.6558	0.5469	0.8741	0.053*
C2	0.7347 (2)	0.5802 (3)	0.93299 (8)	0.0511 (7)
H2	0.6738	0.6303	0.9474	0.061*
C3	0.8362 (2)	0.5540 (3)	0.95425 (8)	0.0430 (7)
C4	0.9276 (2)	0.4826 (3)	0.93441 (8)	0.0479 (7)
H4	0.9959	0.4667	0.9500	0.057*
C5	0.9171 (2)	0.4339 (3)	0.89050 (8)	0.0402 (6)
H5	0.9792	0.3861	0.8762	0.048*
C6	0.81520 (19)	0.4557 (3)	0.86779 (7)	0.0300 (5)
C7	0.79209 (19)	0.3964 (3)	0.82191 (7)	0.0315 (5)
C8	0.87407 (18)	0.2428 (3)	0.75895 (7)	0.0258 (5)
C9	0.67935 (17)	0.2104 (3)	0.67201 (7)	0.0254 (5)
C10	0.64585 (18)	0.1018 (3)	0.63505 (7)	0.0263 (5)
C11	0.6553 (2)	0.1549 (3)	0.59144 (7)	0.0383 (6)
H11	0.6838	0.2563	0.5858	0.046*
C12	0.6228 (2)	0.0589 (3)	0.55647 (8)	0.0481 (7)
H12	0.6300	0.0931	0.5271	0.058*
C13	0.5797 (2)	−0.0878 (3)	0.56616 (9)	0.0503 (7)
C15	0.6004 (2)	−0.0473 (3)	0.64350 (8)	0.0360 (6)
H15	0.5929	−0.0828	0.6727	0.043*
F1	0.84583 (15)	0.6012 (2)	0.99733 (5)	0.0681 (5)
F2	0.54797 (19)	−0.1828 (2)	0.53146 (6)	0.0870 (7)
C14	0.5660 (2)	−0.1434 (3)	0.60860 (9)	0.0491 (7)
H14	0.5344	−0.2433	0.6139	0.059*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
S1	0.0271 (3)	0.0533 (4)	0.0412 (4)	0.0032 (3)	−0.0018 (3)	−0.0162 (3)
O1	0.0387 (11)	0.0887 (16)	0.0482 (11)	0.0263 (10)	−0.0169 (9)	−0.0332 (11)
O2	0.0344 (9)	0.0280 (9)	0.0359 (9)	0.0044 (8)	−0.0042 (7)	−0.0043 (7)
N1	0.0248 (9)	0.0357 (11)	0.0242 (9)	−0.0003 (8)	−0.0042 (8)	−0.0055 (8)
N2	0.0269 (10)	0.0392 (12)	0.0262 (10)	0.0057 (9)	−0.0042 (8)	−0.0118 (9)
N3	0.0280 (9)	0.0286 (10)	0.0270 (10)	0.0032 (9)	−0.0059 (8)	−0.0073 (8)
C1	0.0390 (15)	0.0567 (18)	0.0374 (14)	0.0123 (13)	−0.0061 (12)	−0.0095 (13)
C2	0.0505 (17)	0.0635 (19)	0.0394 (15)	0.0131 (15)	0.0054 (13)	−0.0154 (14)
C3	0.0531 (17)	0.0494 (17)	0.0265 (13)	−0.0062 (14)	−0.0001 (12)	−0.0112 (12)
C4	0.0389 (14)	0.067 (2)	0.0377 (15)	0.0004 (14)	−0.0096 (12)	−0.0118 (14)
C5	0.0347 (14)	0.0535 (17)	0.0323 (13)	0.0045 (12)	−0.0021 (11)	−0.0116 (12)
C6	0.0316 (13)	0.0303 (13)	0.0280 (12)	−0.0002 (10)	−0.0017 (10)	−0.0027 (11)
C7	0.0300 (12)	0.0332 (14)	0.0314 (13)	0.0042 (10)	−0.0046 (10)	−0.0026 (11)
C8	0.0294 (12)	0.0253 (12)	0.0228 (11)	−0.0025 (10)	−0.0034 (10)	0.0009 (9)
C9	0.0214 (11)	0.0280 (13)	0.0267 (12)	−0.0014 (10)	0.0019 (9)	−0.0010 (10)
C10	0.0233 (11)	0.0289 (13)	0.0267 (12)	0.0027 (10)	−0.0056 (9)	−0.0036 (10)
C11	0.0464 (14)	0.0374 (15)	0.0313 (13)	−0.0068 (13)	−0.0024 (11)	0.0013 (12)
C12	0.0634 (18)	0.0546 (18)	0.0261 (13)	−0.0020 (15)	−0.0060 (12)	−0.0041 (13)
C13	0.0603 (18)	0.0505 (18)	0.0399 (16)	−0.0067 (15)	−0.0182 (13)	−0.0189 (14)
C15	0.0390 (14)	0.0368 (15)	0.0321 (13)	−0.0051 (12)	−0.0082 (11)	0.0020 (11)
F1	0.0741 (11)	0.0980 (14)	0.0322 (8)	−0.0006 (10)	−0.0036 (8)	−0.0258 (9)
F2	0.1324 (18)	0.0781 (14)	0.0506 (11)	−0.0280 (12)	−0.0284 (11)	−0.0258 (10)
C14	0.0589 (18)	0.0370 (16)	0.0514 (17)	−0.0158 (14)	−0.0154 (14)	−0.0037 (13)

Geometric parameters (Å, º) top

S1—C8	1.650 (2)	C4—C5	1.385 (3)
O1—C7	1.217 (3)	C4—H4	0.9300
O2—C9	1.235 (3)	C5—C6	1.378 (3)
N1—C7	1.371 (3)	C5—H5	0.9300
N1—C8	1.393 (3)	C6—C7	1.488 (3)
N1—H1A	0.8600	C9—C10	1.488 (3)
N2—C8	1.333 (3)	C10—C15	1.384 (3)
N2—N3	1.381 (2)	C10—C11	1.387 (3)
N2—H2A	0.8600	C11—C12	1.377 (3)
N3—C9	1.338 (3)	C11—H11	0.9300
N3—H3	0.8600	C12—C13	1.362 (4)
C1—C2	1.382 (3)	C12—H12	0.9300
C1—C6	1.385 (3)	C13—F2	1.363 (3)
C1—H1	0.9300	C13—C14	1.366 (4)
C2—C3	1.359 (4)	C15—C14	1.381 (3)
C2—H2	0.9300	C15—H15	0.9300
C3—F1	1.357 (3)	C14—H14	0.9300
C3—C4	1.358 (4)

C7—N1—C8	127.43 (18)	O1—C7—N1	121.7 (2)
C7—N1—H1A	116.3	O1—C7—C6	120.2 (2)
C8—N1—H1A	116.3	N1—C7—C6	118.04 (19)
C8—N2—N3	121.27 (18)	N2—C8—N1	114.95 (18)
C8—N2—H2A	119.4	N2—C8—S1	123.80 (16)
N3—N2—H2A	119.4	N1—C8—S1	121.23 (15)
C9—N3—N2	117.80 (18)	O2—C9—N3	122.6 (2)
C9—N3—H3	121.1	O2—C9—C10	121.8 (2)
N2—N3—H3	121.1	N3—C9—C10	115.58 (19)
C2—C1—C6	121.0 (2)	C15—C10—C11	119.7 (2)
C2—C1—H1	119.5	C15—C10—C9	121.3 (2)
C6—C1—H1	119.5	C11—C10—C9	119.0 (2)
C3—C2—C1	118.0 (2)	C12—C11—C10	120.5 (2)
C3—C2—H2	121.0	C12—C11—H11	119.7
C1—C2—H2	121.0	C10—C11—H11	119.7
F1—C3—C4	118.8 (2)	C13—C12—C11	118.0 (2)
F1—C3—C2	118.1 (2)	C13—C12—H12	121.0
C4—C3—C2	123.0 (2)	C11—C12—H12	121.0
C3—C4—C5	118.6 (2)	C12—C13—F2	117.8 (2)
C3—C4—H4	120.7	C12—C13—C14	123.5 (2)
C5—C4—H4	120.7	F2—C13—C14	118.7 (3)
C6—C5—C4	120.5 (2)	C14—C15—C10	120.1 (2)
C6—C5—H5	119.8	C14—C15—H15	119.9
C4—C5—H5	119.8	C10—C15—H15	119.9
C5—C6—C1	118.9 (2)	C13—C14—C15	118.2 (3)
C5—C6—C7	124.6 (2)	C13—C14—H14	120.9
C1—C6—C7	116.4 (2)	C15—C14—H14	120.9

C8—N2—N3—C9	−138.7 (2)	C7—N1—C8—N2	−0.5 (3)
C6—C1—C2—C3	0.0 (4)	C7—N1—C8—S1	−178.67 (18)
C1—C2—C3—F1	−179.2 (3)	N2—N3—C9—O2	6.9 (3)
C1—C2—C3—C4	0.5 (5)	N2—N3—C9—C10	−171.47 (17)
F1—C3—C4—C5	179.6 (3)	O2—C9—C10—C15	−127.2 (2)
C2—C3—C4—C5	−0.1 (4)	N3—C9—C10—C15	51.2 (3)
C3—C4—C5—C6	−0.9 (4)	O2—C9—C10—C11	49.5 (3)
C4—C5—C6—C1	1.4 (4)	N3—C9—C10—C11	−132.0 (2)
C4—C5—C6—C7	−175.0 (2)	C15—C10—C11—C12	−1.9 (4)
C2—C1—C6—C5	−1.0 (4)	C9—C10—C11—C12	−178.6 (2)
C2—C1—C6—C7	175.7 (3)	C10—C11—C12—C13	1.1 (4)
C8—N1—C7—O1	−6.0 (4)	C11—C12—C13—F2	−179.8 (3)
C8—N1—C7—C6	171.2 (2)	C11—C12—C13—C14	0.7 (4)
C5—C6—C7—O1	172.8 (3)	C11—C10—C15—C14	0.9 (4)
C1—C6—C7—O1	−3.6 (4)	C9—C10—C15—C14	177.6 (2)
C5—C6—C7—N1	−4.4 (4)	C12—C13—C14—C15	−1.7 (4)
C1—C6—C7—N1	179.1 (2)	F2—C13—C14—C15	178.8 (3)
N3—N2—C8—N1	−174.21 (18)	C10—C15—C14—C13	0.8 (4)
N3—N2—C8—S1	3.9 (3)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N2—H2A···O1	0.86	1.89	2.571 (2)	135
N2—H2A···S1ⁱ	0.86	2.84	3.3875 (18)	123
N1—H1A···O2ⁱⁱ	0.86	2.33	3.165 (2)	165
N3—H3···O2ⁱⁱⁱ	0.86	2.10	2.942 (2)	166
C4—H4···F1^iv	0.93	2.49	3.409 (3)	169
C5—H5···O2ⁱⁱ	0.93	2.45	3.345 (3)	160

Symmetry codes: (i) x−1/2, y, −z+3/2; (ii) x+1/2, y, −z+3/2; (iii) −x+3/2, y−1/2, z; (iv) −x+2, −y+1, −z+2.

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N2—H2A···O1	0.86	1.89	2.571 (2)	135
N2—H2A···S1ⁱ	0.86	2.84	3.3875 (18)	123
N1—H1A···O2ⁱⁱ	0.86	2.33	3.165 (2)	165
N3—H3···O2ⁱⁱⁱ	0.86	2.10	2.942 (2)	166
C4—H4···F1^iv	0.93	2.49	3.409 (3)	169
C5—H5···O2ⁱⁱ	0.93	2.45	3.345 (3)	160

Symmetry codes: (i) x−1/2, y, −z+3/2; (ii) x+1/2, y, −z+3/2; (iii) −x+3/2, y−1/2, z; (iv) −x+2, −y+1, −z+2.

Acknowledgements

The authors thank Universiti Kebangsaan Malaysia and the Ministry of Science and Technology, Malaysia, for research grants DLP-2013-009 and DIP-2012-11, and the Centre of Research and Instrumentation (CRIM) for research facilities.

References

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ISSN: 2056-9890

Volume 70| Part 9| September 2014| Pages o915-o916

doi:10.1107/S1600536814015761

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organic compounds\(\def\hfill{\hskip 5em}\def\hfil{\hskip 3em}\def\eqno#1{\hfil {#1}}\)

Crystal structure of 4-fluoro-N-[2-(4-fluoro­benzo­yl)hydra­zine-1-carbono­thio­yl]benzamide

1. Related literature

2. Experimental

2.1. Crystal data

2.2. Data collection

2.3. Refinement

Supporting information

Acknowledgements

References

organic compounds

Crystal structure of 4-fluoro-N-[2-(4-fluorobenzoyl)hydrazine-1-carbonothioyl]benzamide