1-[1-(4-Bromo­phen­yl)ethyl­idene]-4-(2,4-dimeth­oxy­phen­yl)thio­semicarbazide

Yaqub, M.; Pervez, H.; Arif, N.; Tahir, M.N.; Hussain, M.

doi:10.1107/S1600536810022622

organic compounds

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ISSN: 2056-9890

Volume 66| Part 7| July 2010| Page o1696

doi:10.1107/S1600536810022622

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1-[1-(4-Bromophenyl)ethylidene]-4-(2,4-dimethoxyphenyl)thiosemicarbazide

Muhammad Yaqub,^a Humayun Pervez,^a Nadia Arif,^a M. Nawaz Tahir ^b ^* and Mazhar Hussain ^a

^aDepartment of Chemistry, Bahauddin Zakariya University, Multan 60800, Pakistan, and ^bDepartment of Physics, University of Sargodha, Sargodha, Pakistan
^*Correspondence e-mail: dmntahir_uos@yahoo.com

(Received 12 June 2010; accepted 12 June 2010; online 18 June 2010)

In the title compound, C₁₇H₁₈BrN₃O₂S, the dihedral angle between the aromatic rings is 9.15 (17)°. A bifurcated intramolecular N—H⋯(N,O) hydrogen bond generates two S(5) rings and a weak intramolecular C—H⋯S interaction completes an S(6) ring motif. In the crystal, inversion dimers linked by pairs of N—H⋯S hydrogen bonds generate R₂²(8) loops and weak C—H⋯S and C—H⋯π interactions are also present.

Related literature

For the pharmacological applications of thiosemicarbazones see: Beraldo & Gambino (2004 ); Pervez et al. (2008 , 2010a ,b ). For related structures, see: Jian et al. (2005 ); Martínez et al. (2006 ). For graph-set notation, see: Bernstein et al. (1995 ).

Experimental

Crystal data

C₁₇H₁₈BrN₃O₂S
M_r = 408.31
Monoclinic, P 2₁ /n
a = 5.8390 (2) Å
b = 30.3335 (11) Å
c = 9.9423 (4) Å
β = 94.910 (2)°
V = 1754.49 (11) Å³
Z = 4
Mo Kα radiation
μ = 2.48 mm⁻¹
T = 296 K
0.25 × 0.22 × 0.20 mm

Data collection

Bruker Kappa APEXII CCD diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2005 ) T_min = 0.642, T_max = 0.652
17115 measured reflections
4346 independent reflections
2654 reflections with I > 2σ(I)
R_int = 0.044

Refinement

R[F² > 2σ(F²)] = 0.041
wR(F²) = 0.100
S = 1.01
4346 reflections
220 parameters
H-atom parameters constrained
Δρ_max = 0.42 e Å⁻³
Δρ_min = −0.36 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

Cg1 is the centroid of C1–C6 ring.

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1⋯O1	0.86	2.12	2.573 (3)	113
N1—H1⋯N3	0.86	2.05	2.538 (3)	115
N2—H2A⋯S1ⁱ	0.86	2.84	3.662 (2)	161
C2—H2⋯S1	0.93	2.58	3.248 (3)	129
C17—H17A⋯S1ⁱⁱ	0.96	2.86	3.774 (3)	161
C8—H8A⋯Cg1ⁱⁱⁱ	0.96	2.98	3.860 (3)	153
Symmetry codes: (i) -x+2, -y, -z+2; (ii) x+1, y, z; (iii) x-1, y, z.

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 ) 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/S1600536810022622/hb5499sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536810022622/hb5499Isup2.hkl

checkCIF report

Comment top

Thiosemicarbazones have wide pharmacological properties (Beraldo & Gambino, 2004). Prompted by this, we recently reported the synthesis and medicinal importance of some isatins-thiosemicarbazones (Pervez et al., 2008, 2010a,b). Now, we report the synthesis and crystal structure of the title compound (I), (Fig. I).

The crystal structure of (II) i.e. 4-fluoroacetophenone-N-propylthiosemicarbazone (Martinez et al., 2006) and (III) i.e. 4-phenyl-1-(1-phenylethylidene)thiosemicarbazide (Jian, et al., 2005) have been published. The title compound (I) is different from (II) and (III) due to attachment of substituants at the phenyl rings.

In (I), the phenyl ring A (C1–C6) of 2,4-dimethoxyanilino group, B (C11—C16) of 4-bromophenyl are planar with r. m. s. deviations of 0.0034 and 0.0036 Å, respectively. The thiosemicarbazone moiety C (N1—N3/C9/S1) is also planar with r. m. s. deviation of 0.0062 Å from its mean square plane. The dihedral angle between A/B, A/C and B/C is 9.15 (17), 2.07 (17) and 9.12 (16)°, respectively. Two S(5) ring motifs (Bernstein et al., 1995) (Table 1, Fig. 1) are formed due to strong intramolecular H-bonding of N—H···N and N—H···O types. The weak interaction of C—H···S type completes an S(6) ring motif. The molecules are dimerized due to intermolecular interactions of N—H···S type and complete R₂²(8) ring motif (Fig. 2). The dimers are interlinked through C—H···S interactions (Table 1). The C—H···π interaction (Table 1) also play role in stabilizing the molecules.

Related literature top

For the pharmacological applications of thiosemicarbazones see: Beraldo & Gambino (2004); Pervez et al. (2008, 2010a,b). For related structures, see: Jian et al. (2005); Martínez et al. (2006). For graph-set notation, see: Bernstein et al. (1995).

Experimental top

A solution of 4-(2,4-dimethoxyphenyl)thiosemicarbazide (0.15 g, 0.66 mole) in warm ethanol (20 ml) was added drop wise to the stirred solution of 4-bromoacetophenone (0.13 g, 0.66 mol) in warm ethanol (10 ml) containing 2–3 drops of acetic acid. The resultant mixture was then heated under reflux for 30 min. After cooling the reaction mixture to room temperature, the yellow solid was collected by suction filtration, washing with ethanol furnished the title compound in pure form (0.21 g, 95%), m.p. 502 K. Colourless prisms of (I) were grown in chloroform-petroleum ether (1:5) system at room temperature by diffusion method.

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) and PLATON (Spek, 2009); software used to prepare material for publication: WinGX (Farrugia, 1999) and PLATON (Spek, 2009).

Figures top

	Fig. 1. View of (I) with displacement ellipsoids drawn at the 50% probability level. The dotted lines indicate the intra-molecular H-bonds.
	Fig. 2. The partial packing of (I), which shows that molecules form dimers.

1-[1-(4-Bromophenyl)ethylidene]-4-(2,4-dimethoxyphenyl)thiosemicarbazide top

Crystal data top

C₁₇H₁₈BrN₃O₂S	F(000) = 832
M_r = 408.31	D_x = 1.546 Mg m⁻³
Monoclinic, P2₁/n	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2yn	Cell parameters from 2654 reflections
a = 5.8390 (2) Å	θ = 2.2–28.3°
b = 30.3335 (11) Å	µ = 2.48 mm⁻¹
c = 9.9423 (4) Å	T = 296 K
β = 94.910 (2)°	Prism, colorless
V = 1754.49 (11) Å³	0.25 × 0.22 × 0.20 mm
Z = 4

Data collection top

Bruker Kappa APEXII CCD diffractometer	4346 independent reflections
Radiation source: fine-focus sealed tube	2654 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.044
Detector resolution: 7.5 pixels mm^-1	θ_max = 28.3°, θ_min = 2.2°
ω scans	h = −4→7
Absorption correction: multi-scan (SADABS; Bruker, 2005)	k = −40→40
T_min = 0.642, T_max = 0.652	l = −13→13
17115 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)] = 0.041	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.100	H-atom parameters constrained
S = 1.01	w = 1/[σ²(F_o²) + (0.0413P)² + 0.4088P] where P = (F_o² + 2F_c²)/3
4346 reflections	(Δ/σ)_max = 0.001
220 parameters	Δρ_max = 0.42 e Å⁻³
0 restraints	Δρ_min = −0.36 e Å⁻³

Crystal data top

C₁₇H₁₈BrN₃O₂S	V = 1754.49 (11) Å³
M_r = 408.31	Z = 4
Monoclinic, P2₁/n	Mo Kα radiation
a = 5.8390 (2) Å	µ = 2.48 mm⁻¹
b = 30.3335 (11) Å	T = 296 K
c = 9.9423 (4) Å	0.25 × 0.22 × 0.20 mm
β = 94.910 (2)°

Data collection top

Bruker Kappa APEXII CCD diffractometer	4346 independent reflections
Absorption correction: multi-scan (SADABS; Bruker, 2005)	2654 reflections with I > 2σ(I)
T_min = 0.642, T_max = 0.652	R_int = 0.044
17115 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.041	0 restraints
wR(F²) = 0.100	H-atom parameters constrained
S = 1.01	Δρ_max = 0.42 e Å⁻³
4346 reflections	Δρ_min = −0.36 e Å⁻³
220 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
Br1	1.68144 (7)	0.28876 (1)	0.66065 (3)	0.0846 (1)
S1	0.69373 (12)	0.00989 (2)	0.87217 (7)	0.0577 (2)
O1	0.7242 (3)	0.14610 (6)	0.55058 (18)	0.0598 (7)
O2	0.0390 (3)	0.09126 (7)	0.3147 (2)	0.0710 (8)
N1	0.7530 (3)	0.08160 (7)	0.7192 (2)	0.0504 (7)
N2	1.0174 (3)	0.06989 (7)	0.8946 (2)	0.0490 (7)
N3	1.1192 (3)	0.10729 (7)	0.8520 (2)	0.0465 (7)
C1	0.5629 (4)	0.08091 (8)	0.6222 (2)	0.0453 (8)
C2	0.3956 (5)	0.04927 (10)	0.6085 (3)	0.0684 (11)
C3	0.2178 (5)	0.05173 (10)	0.5075 (3)	0.0707 (11)
C4	0.2059 (4)	0.08609 (9)	0.4186 (3)	0.0536 (9)
C5	0.3721 (4)	0.11870 (9)	0.4316 (3)	0.0519 (9)
C6	0.5493 (4)	0.11606 (8)	0.5315 (2)	0.0449 (8)
C7	0.7459 (5)	0.17845 (10)	0.4497 (3)	0.0718 (11)
C8	−0.1278 (5)	0.05715 (11)	0.2945 (3)	0.0714 (11)
C9	0.8214 (4)	0.05526 (8)	0.8225 (2)	0.0426 (8)
C10	1.2991 (4)	0.12299 (8)	0.9180 (2)	0.0413 (8)
C11	1.3922 (4)	0.16334 (8)	0.8596 (2)	0.0397 (7)
C12	1.2659 (4)	0.18592 (9)	0.7571 (3)	0.0522 (9)
C13	1.3493 (5)	0.22333 (9)	0.7001 (3)	0.0585 (10)
C14	1.5632 (4)	0.23844 (9)	0.7440 (3)	0.0511 (9)
C15	1.6935 (5)	0.21732 (9)	0.8453 (3)	0.0560 (10)
C16	1.6074 (4)	0.17997 (9)	0.9025 (3)	0.0508 (9)
C17	1.4082 (5)	0.10312 (9)	1.0456 (3)	0.0565 (9)
H1	0.84389	0.10350	0.71009	0.0605*
H2	0.40157	0.02564	0.66831	0.0820*
H2A	1.07456	0.05588	0.96481	0.0587*
H3	0.10583	0.02985	0.50022	0.0849*
H5	0.36375	0.14251	0.37241	0.0623*
H7A	0.61321	0.19727	0.44397	0.1075*
H7B	0.75783	0.16426	0.36429	0.1075*
H7C	0.88133	0.19576	0.47252	0.1075*
H8A	−0.21919	0.05609	0.37027	0.1075*
H8B	−0.05148	0.02938	0.28602	0.1075*
H8C	−0.22514	0.06296	0.21373	0.1075*
H12	1.12106	0.17552	0.72613	0.0626*
H13	1.26085	0.23820	0.63226	0.0701*
H15	1.83820	0.22799	0.87536	0.0672*
H16	1.69579	0.16564	0.97145	0.0610*
H17A	1.48971	0.07685	1.02462	0.0848*
H17B	1.29134	0.09589	1.10418	0.0848*
H17C	1.51361	0.12388	1.08973	0.0848*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Br1	0.1088 (3)	0.0700 (2)	0.0736 (2)	−0.0456 (2)	0.0001 (2)	0.0106 (2)
S1	0.0585 (4)	0.0489 (4)	0.0642 (4)	−0.0114 (3)	−0.0030 (3)	0.0194 (3)
O1	0.0677 (12)	0.0508 (11)	0.0587 (12)	−0.0148 (9)	−0.0080 (9)	0.0172 (9)
O2	0.0668 (12)	0.0697 (14)	0.0712 (13)	0.0015 (11)	−0.0242 (10)	0.0076 (11)
N1	0.0543 (12)	0.0453 (12)	0.0496 (12)	−0.0150 (10)	−0.0074 (10)	0.0128 (10)
N2	0.0522 (12)	0.0458 (12)	0.0470 (12)	−0.0095 (10)	−0.0066 (10)	0.0129 (10)
N3	0.0493 (12)	0.0431 (12)	0.0464 (12)	−0.0070 (9)	−0.0005 (10)	0.0087 (9)
C1	0.0483 (14)	0.0439 (14)	0.0429 (13)	−0.0044 (11)	−0.0008 (11)	0.0061 (11)
C2	0.077 (2)	0.0571 (18)	0.0670 (19)	−0.0215 (15)	−0.0181 (16)	0.0215 (15)
C3	0.0721 (19)	0.063 (2)	0.072 (2)	−0.0253 (16)	−0.0223 (16)	0.0155 (16)
C4	0.0529 (16)	0.0520 (16)	0.0540 (16)	0.0031 (12)	−0.0056 (13)	−0.0032 (13)
C5	0.0644 (17)	0.0443 (14)	0.0462 (15)	0.0062 (12)	−0.0006 (13)	0.0072 (11)
C6	0.0517 (15)	0.0390 (13)	0.0442 (14)	−0.0022 (11)	0.0051 (12)	0.0012 (10)
C7	0.090 (2)	0.0543 (19)	0.070 (2)	−0.0172 (16)	0.0010 (17)	0.0197 (15)
C8	0.0591 (18)	0.076 (2)	0.075 (2)	0.0018 (16)	−0.0180 (15)	−0.0104 (17)
C9	0.0461 (14)	0.0407 (13)	0.0412 (13)	−0.0013 (10)	0.0043 (11)	0.0027 (10)
C10	0.0435 (14)	0.0416 (13)	0.0384 (13)	0.0037 (10)	0.0018 (11)	−0.0006 (10)
C11	0.0417 (13)	0.0388 (13)	0.0384 (12)	−0.0005 (10)	0.0025 (10)	−0.0044 (10)
C12	0.0475 (15)	0.0506 (15)	0.0572 (16)	−0.0094 (12)	−0.0030 (12)	0.0095 (13)
C13	0.0617 (18)	0.0552 (17)	0.0567 (17)	−0.0082 (13)	−0.0053 (14)	0.0109 (13)
C14	0.0603 (16)	0.0469 (15)	0.0465 (15)	−0.0135 (12)	0.0075 (13)	−0.0047 (12)
C15	0.0539 (16)	0.0591 (18)	0.0544 (16)	−0.0181 (13)	0.0004 (13)	−0.0090 (13)
C16	0.0507 (15)	0.0525 (16)	0.0480 (14)	−0.0024 (12)	−0.0029 (12)	0.0005 (12)
C17	0.0650 (17)	0.0505 (16)	0.0515 (16)	−0.0036 (13)	−0.0099 (13)	0.0063 (12)

Geometric parameters (Å, º) top

Br1—C14	1.895 (3)	C11—C12	1.387 (4)
S1—C9	1.660 (2)	C12—C13	1.376 (4)
O1—C6	1.370 (3)	C13—C14	1.366 (4)
O1—C7	1.417 (3)	C14—C15	1.368 (4)
O2—C4	1.367 (3)	C15—C16	1.382 (4)
O2—C8	1.423 (4)	C2—H2	0.9300
N1—C1	1.407 (3)	C3—H3	0.9300
N1—C9	1.335 (3)	C5—H5	0.9300
N2—N3	1.365 (3)	C7—H7A	0.9600
N2—C9	1.371 (3)	C7—H7B	0.9600
N3—C10	1.282 (3)	C7—H7C	0.9600
N1—H1	0.8600	C8—H8A	0.9600
N2—H2A	0.8600	C8—H8B	0.9600
C1—C2	1.368 (4)	C8—H8C	0.9600
C1—C6	1.394 (3)	C12—H12	0.9300
C2—C3	1.383 (4)	C13—H13	0.9300
C3—C4	1.365 (4)	C15—H15	0.9300
C4—C5	1.384 (4)	C16—H16	0.9300
C5—C6	1.374 (3)	C17—H17A	0.9600
C10—C11	1.478 (3)	C17—H17B	0.9600
C10—C17	1.497 (4)	C17—H17C	0.9600
C11—C16	1.387 (3)

C6—O1—C7	118.27 (19)	C14—C15—C16	119.2 (3)
C4—O2—C8	117.3 (2)	C11—C16—C15	121.6 (3)
C1—N1—C9	133.2 (2)	C1—C2—H2	119.00
N3—N2—C9	118.23 (19)	C3—C2—H2	119.00
N2—N3—C10	120.6 (2)	C2—C3—H3	120.00
C9—N1—H1	113.00	C4—C3—H3	120.00
C1—N1—H1	113.00	C4—C5—H5	120.00
N3—N2—H2A	121.00	C6—C5—H5	120.00
C9—N2—H2A	121.00	O1—C7—H7A	109.00
C2—C1—C6	118.1 (2)	O1—C7—H7B	109.00
N1—C1—C6	115.5 (2)	O1—C7—H7C	109.00
N1—C1—C2	126.4 (2)	H7A—C7—H7B	109.00
C1—C2—C3	121.3 (3)	H7A—C7—H7C	109.00
C2—C3—C4	120.3 (3)	H7B—C7—H7C	109.00
O2—C4—C3	124.8 (2)	O2—C8—H8A	109.00
O2—C4—C5	115.9 (2)	O2—C8—H8B	109.00
C3—C4—C5	119.3 (3)	O2—C8—H8C	109.00
C4—C5—C6	120.3 (3)	H8A—C8—H8B	109.00
O1—C6—C5	124.6 (2)	H8A—C8—H8C	109.00
C1—C6—C5	120.7 (2)	H8B—C8—H8C	109.00
O1—C6—C1	114.75 (19)	C11—C12—H12	119.00
S1—C9—N1	127.77 (18)	C13—C12—H12	119.00
S1—C9—N2	119.25 (17)	C12—C13—H13	120.00
N1—C9—N2	112.9 (2)	C14—C13—H13	120.00
C11—C10—C17	121.5 (2)	C14—C15—H15	120.00
N3—C10—C11	114.80 (19)	C16—C15—H15	120.00
N3—C10—C17	123.7 (2)	C11—C16—H16	119.00
C10—C11—C16	122.3 (2)	C15—C16—H16	119.00
C12—C11—C16	117.2 (2)	C10—C17—H17A	109.00
C10—C11—C12	120.5 (2)	C10—C17—H17B	109.00
C11—C12—C13	121.7 (2)	C10—C17—H17C	109.00
C12—C13—C14	119.4 (3)	H17A—C17—H17B	109.00
Br1—C14—C13	119.2 (2)	H17A—C17—H17C	109.00
C13—C14—C15	120.9 (3)	H17B—C17—H17C	110.00
Br1—C14—C15	119.90 (19)

C7—O1—C6—C1	169.2 (2)	C2—C3—C4—O2	179.3 (3)
C7—O1—C6—C5	−10.1 (3)	C2—C3—C4—C5	−0.8 (4)
C8—O2—C4—C3	−3.1 (4)	O2—C4—C5—C6	−178.9 (2)
C8—O2—C4—C5	176.9 (2)	C3—C4—C5—C6	1.1 (4)
C9—N1—C1—C2	−2.8 (4)	C4—C5—C6—O1	178.5 (2)
C9—N1—C1—C6	178.0 (2)	C4—C5—C6—C1	−0.8 (4)
C1—N1—C9—S1	0.2 (4)	N3—C10—C11—C12	11.5 (3)
C1—N1—C9—N2	−177.7 (2)	N3—C10—C11—C16	−167.7 (2)
C9—N2—N3—C10	178.1 (2)	C17—C10—C11—C12	−167.6 (2)
N3—N2—C9—S1	−179.91 (16)	C17—C10—C11—C16	13.1 (4)
N3—N2—C9—N1	−1.8 (3)	C10—C11—C12—C13	−179.4 (2)
N2—N3—C10—C11	179.44 (19)	C16—C11—C12—C13	−0.1 (4)
N2—N3—C10—C17	−1.4 (3)	C10—C11—C16—C15	178.9 (2)
N1—C1—C2—C3	−179.0 (3)	C12—C11—C16—C15	−0.3 (4)
C6—C1—C2—C3	0.2 (4)	C11—C12—C13—C14	0.9 (4)
N1—C1—C6—O1	0.1 (3)	C12—C13—C14—Br1	177.8 (2)
N1—C1—C6—C5	179.5 (2)	C12—C13—C14—C15	−1.2 (4)
C2—C1—C6—O1	−179.3 (2)	Br1—C14—C15—C16	−178.2 (2)
C2—C1—C6—C5	0.2 (4)	C13—C14—C15—C16	0.7 (4)
C1—C2—C3—C4	0.1 (4)	C14—C15—C16—C11	0.1 (4)

Hydrogen-bond geometry (Å, º) top

Cg1 is the centroid of C1–C6 ring.

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1···O1	0.86	2.12	2.573 (3)	113
N1—H1···N3	0.86	2.05	2.538 (3)	115
N2—H2A···S1ⁱ	0.86	2.84	3.662 (2)	161
C2—H2···S1	0.93	2.58	3.248 (3)	129
C17—H17A···S1ⁱⁱ	0.96	2.86	3.774 (3)	161
C8—H8A···Cg1ⁱⁱⁱ	0.96	2.98	3.860 (3)	153

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

Experimental details

Crystal data
Chemical formula	C₁₇H₁₈BrN₃O₂S
M_r	408.31
Crystal system, space group	Monoclinic, P2₁/n
Temperature (K)	296
a, b, c (Å)	5.8390 (2), 30.3335 (11), 9.9423 (4)
β (°)	94.910 (2)
V (Å³)	1754.49 (11)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	2.48
Crystal size (mm)	0.25 × 0.22 × 0.20

Data collection
Diffractometer	Bruker Kappa APEXII CCD diffractometer
Absorption correction	Multi-scan (SADABS; Bruker, 2005)
T_min, T_max	0.642, 0.652
No. of measured, independent and observed [I > 2σ(I)] reflections	17115, 4346, 2654
R_int	0.044
(sin θ/λ)_max (Å⁻¹)	0.668

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.041, 0.100, 1.01
No. of reflections	4346
No. of parameters	220
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.42, −0.36

Computer programs: APEX2 (Bruker, 2007), SAINT (Bruker, 2007), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), ORTEP-3 (Farrugia, 1997) and PLATON (Spek, 2009), WinGX (Farrugia, 1999) and PLATON (Spek, 2009).

Hydrogen-bond geometry (Å, º) top

Cg1 is the centroid of C1–C6 ring.

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1···O1	0.86	2.12	2.573 (3)	113
N1—H1···N3	0.86	2.05	2.538 (3)	115
N2—H2A···S1ⁱ	0.86	2.84	3.662 (2)	161
C2—H2···S1	0.93	2.58	3.248 (3)	129
C17—H17A···S1ⁱⁱ	0.96	2.86	3.774 (3)	161
C8—H8A···Cg1ⁱⁱⁱ	0.96	2.98	3.860 (3)	153

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

Acknowledgements

NA gratefully acknowledges the Higher Education Commission (HEC), Islamabad, Pakistan, for providing her with a Scholarship under the Indigenous PhD Program and also for partial funding of this research work.

References

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Volume 66| Part 7| July 2010| Page o1696

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

1-[1-(4-Bromo­phen­yl)ethyl­­idene]-4-(2,4-dimeth­­oxy­phen­yl)thio­semicarbazide

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Experimental

Crystal data

Data collection

Refinement

Supporting information

Acknowledgements

References

organic compounds

1-[1-(4-Bromophenyl)ethylidene]-4-(2,4-dimethoxyphenyl)thiosemicarbazide