2-(4-Bromo­phenoxy)-N-[5-(E)-styryl-1,3,4-thia­diazol-2-yl]acet­amide

In the title compound, C₁₈H₁₄BrN₃O₂S, the three rings are nearly coplanar. In the crystal structure, intermolecular N—H...N and C—H...O hydrogen-bond interactions link the mol­ecules into ribbons, displaying alternate rings of graph-set motifs R₂²(8) and R₂²(14).

Key indicators

• Single-crystal X-ray study
• T = 292 K
• Mean [sigma](C-C) = 0.009 Å
• R factor = 0.068
• wR factor = 0.185
• Data-to-parameter ratio = 17.2

checkCIF/PLATON results

No syntax errors found



Alert level C
RINTA01_ALERT_3_C  The value of Rint is greater than 0.10
            Rint given   0.119
PLAT020_ALERT_3_C The value of Rint is greater than 0.10 .........       0.12
PLAT242_ALERT_2_C Check Low       Ueq as Compared to Neighbors for         C6
PLAT242_ALERT_2_C Check Low       Ueq as Compared to Neighbors for        C16
PLAT322_ALERT_2_C Check Hybridisation of  S1     in Main Residue .          ?
PLAT341_ALERT_3_C Low Bond Precision on C-C bonds (x 1000) Ang ...          9

   0 ALERT level A = In general: serious problem
   0 ALERT level B = Potentially serious problem
   6 ALERT level C = Check and explain
   0 ALERT level G = General alerts; check

   0 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
   3 ALERT type 2 Indicator that the structure model may be wrong or deficient
   3 ALERT type 3 Indicator that the structure quality may be low
   0 ALERT type 4 Improvement, methodology, query or suggestion

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Computing details

Data collection: SMART (Siemens, 1995); cell refinement: SAINT (Siemens, 1995); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 1990); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: SHELXTL (Siemens, 1995); software used to prepare material for publication: SHELXTL.

N-[5-(1E)-Styryl-1,3,4-thiadiazol-2-yl]-4-Bromophenoxy-acetamide

Crystal data

C18H14BrN3O2S	Z = 2
Mr = 416.29	F(000) = 420
Triclinic, P1	Dx = 1.544 Mg m^−3
Hall symbol: -p 1	Melting point: 525 K
a = 5.1151 (9) Å	Mo Kα radiation, λ = 0.71073 Å
b = 9.5790 (18) Å	Cell parameters from 1434 reflections
c = 18.426 (3) Å	θ = 2.4–19.8°
α = 87.292 (3)°	µ = 2.43 mm^−1
β = 83.782 (3)°	T = 292 K
γ = 87.021 (4)°	Plate, colourless
V = 895.5 (3) Å^3	0.40 × 0.16 × 0.04 mm

Data collection

Bruker SMART CCD area-detector diffractometer	3898 independent reflections
Radiation source: fine-focus sealed tube	1930 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.119
φ and ω scans	θmax = 27.0°, θmin = 1.1°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −6→6
Tmin = 0.443, Tmax = 0.909	k = −12→12
10201 measured reflections	l = −23→23

Refinement

Refinement on F^2	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F^2 > 2σ(F^2)] = 0.068	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.185	H-atom parameters constrained
S = 0.97	w = 1/[σ^2(Fo^2) + (0.0683P)^2] where P = (Fo^2 + 2Fc^2)/3
3898 reflections	(Δ/σ)max < 0.001
226 parameters	Δρmax = 0.50 e Å^−3
0 restraints	Δρmin = −0.38 e Å^−3

Special details

Geometry. All e.s.d.'s (except the e.s.d. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell e.s.d.'s are taken into account individually in the estimation of e.s.d.'s in distances, angles and torsion angles; correlations between e.s.d.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell e.s.d.'s is used for estimating e.s.d.'s 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 > 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 (Ų)

	x	y	z	Uiso*/Ueq
Br1	0.97554 (17)	0.28458 (9)	0.17115 (4)	0.1080 (4)
C1	0.2912 (14)	1.2773 (8)	0.9059 (3)	0.086 (2)
H1	0.1581	1.3171	0.8799	0.103*
C2	0.3349 (18)	1.3324 (9)	0.9718 (4)	0.108 (3)
H2	0.2307	1.4081	0.9899	0.130*
C3	0.531 (2)	1.2750 (11)	1.0095 (4)	0.108 (3)
H3	0.5585	1.3113	1.0539	0.130*
C4	0.6852 (18)	1.1660 (10)	0.9835 (4)	0.111 (3)
H4	0.8212	1.1289	1.0093	0.134*
C5	0.6411 (15)	1.1099 (8)	0.9189 (3)	0.092 (2)
H5	0.7463	1.0338	0.9017	0.110*
C6	0.4417 (12)	1.1650 (6)	0.8787 (3)	0.0625 (16)
C7	0.4037 (12)	1.1019 (6)	0.8106 (3)	0.0652 (16)
H7	0.5219	1.0290	0.7959	0.078*
C8	0.2180 (11)	1.1374 (6)	0.7673 (3)	0.0602 (15)
H8	0.0943	1.2074	0.7826	0.072*
C9	0.1918 (11)	1.0765 (6)	0.6983 (3)	0.0551 (14)
C10	0.2230 (9)	0.9565 (5)	0.5878 (3)	0.0451 (12)
C11	0.4672 (10)	0.7761 (5)	0.5185 (3)	0.0464 (12)
C12	0.4607 (10)	0.6983 (5)	0.4504 (3)	0.0517 (13)
H12A	0.3012	0.6469	0.4534	0.062*
H12B	0.4625	0.7634	0.4084	0.062*
C13	0.7298 (10)	0.5363 (5)	0.3789 (3)	0.0466 (12)
C14	0.9436 (10)	0.4403 (5)	0.3761 (3)	0.0525 (13)
H14	1.0389	0.4267	0.4163	0.063*
C15	1.0149 (11)	0.3664 (6)	0.3156 (3)	0.0638 (16)
H15	1.1577	0.3021	0.3143	0.077*
C16	0.8737 (11)	0.3874 (6)	0.2560 (3)	0.0590 (15)
C17	0.6547 (11)	0.4795 (6)	0.2580 (3)	0.0610 (15)
H17	0.5562	0.4907	0.2184	0.073*
C18	0.5862 (10)	0.5540 (6)	0.3198 (3)	0.0576 (14)
H18	0.4412	0.6170	0.3217	0.069*
N1	0.0149 (9)	1.1232 (5)	0.6556 (2)	0.0596 (12)
N2	0.0361 (8)	1.0545 (5)	0.5914 (2)	0.0548 (11)
N3	0.2708 (8)	0.8757 (4)	0.5278 (2)	0.0493 (11)
H3A	0.1687	0.8893	0.4937	0.059*
O1	0.6273 (7)	0.7544 (4)	0.5618 (2)	0.0668 (11)
O2	0.6827 (7)	0.6051 (4)	0.44261 (19)	0.0594 (10)
S1	0.3988 (3)	0.94143 (15)	0.66190 (7)	0.0556 (4)

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
Br1	0.1300 (8)	0.1207 (7)	0.0743 (5)	0.0266 (5)	−0.0123 (5)	−0.0462 (5)
C1	0.097 (5)	0.096 (5)	0.068 (4)	−0.005 (4)	−0.017 (4)	−0.021 (4)
C2	0.127 (7)	0.116 (7)	0.084 (5)	−0.012 (6)	0.000 (5)	−0.049 (5)
C3	0.124 (7)	0.145 (8)	0.065 (5)	−0.047 (6)	−0.023 (5)	−0.022 (5)
C4	0.116 (7)	0.153 (9)	0.073 (5)	−0.016 (6)	−0.037 (5)	−0.014 (5)
C5	0.095 (5)	0.117 (6)	0.067 (4)	−0.003 (5)	−0.024 (4)	−0.012 (4)
C6	0.067 (4)	0.075 (4)	0.046 (3)	−0.017 (3)	−0.002 (3)	−0.007 (3)
C7	0.065 (4)	0.071 (4)	0.060 (4)	−0.001 (3)	−0.007 (3)	−0.008 (3)
C8	0.062 (4)	0.062 (4)	0.057 (3)	−0.004 (3)	0.000 (3)	−0.014 (3)
C9	0.057 (3)	0.061 (4)	0.049 (3)	−0.003 (3)	−0.007 (3)	−0.007 (3)
C10	0.039 (3)	0.054 (3)	0.043 (3)	0.001 (3)	−0.010 (2)	−0.008 (2)
C11	0.044 (3)	0.047 (3)	0.049 (3)	0.004 (2)	−0.012 (2)	−0.001 (2)
C12	0.048 (3)	0.055 (3)	0.052 (3)	0.014 (3)	−0.012 (2)	−0.008 (3)
C13	0.044 (3)	0.046 (3)	0.051 (3)	0.003 (2)	−0.009 (2)	−0.006 (2)
C14	0.048 (3)	0.054 (3)	0.056 (3)	0.009 (3)	−0.014 (3)	−0.009 (3)
C15	0.057 (4)	0.062 (4)	0.072 (4)	0.010 (3)	−0.007 (3)	−0.015 (3)
C16	0.063 (4)	0.062 (4)	0.051 (3)	−0.003 (3)	−0.002 (3)	−0.016 (3)
C17	0.062 (4)	0.068 (4)	0.056 (3)	0.001 (3)	−0.022 (3)	−0.010 (3)
C18	0.052 (3)	0.060 (4)	0.061 (4)	0.010 (3)	−0.015 (3)	−0.002 (3)
N1	0.056 (3)	0.068 (3)	0.056 (3)	0.009 (2)	−0.010 (2)	−0.018 (2)
N2	0.050 (3)	0.063 (3)	0.052 (3)	0.008 (2)	−0.009 (2)	−0.014 (2)
N3	0.043 (2)	0.057 (3)	0.050 (2)	0.013 (2)	−0.0163 (19)	−0.012 (2)
O1	0.066 (2)	0.075 (3)	0.063 (2)	0.028 (2)	−0.030 (2)	−0.015 (2)
O2	0.060 (2)	0.063 (2)	0.056 (2)	0.0254 (19)	−0.0179 (18)	−0.0149 (19)
S1	0.0580 (9)	0.0603 (9)	0.0505 (8)	0.0079 (7)	−0.0173 (7)	−0.0075 (7)

Geometric parameters (Å, º)

Br1—C16	1.897 (5)	C10—S1	1.711 (5)
C1—C6	1.372 (9)	C11—O1	1.208 (5)
C1—C2	1.391 (9)	C11—N3	1.352 (6)
C1—H1	0.9300	C11—C12	1.494 (6)
C2—C3	1.358 (11)	C12—O2	1.407 (6)
C2—H2	0.9300	C12—H12A	0.9700
C3—C4	1.351 (11)	C12—H12B	0.9700
C3—H3	0.9300	C13—O2	1.366 (6)
C4—C5	1.375 (9)	C13—C18	1.377 (7)
C4—H4	0.9300	C13—C14	1.390 (7)
C5—C6	1.392 (8)	C14—C15	1.356 (7)
C5—H5	0.9300	C14—H14	0.9300
C6—C7	1.454 (7)	C15—C16	1.380 (8)
C7—C8	1.327 (7)	C15—H15	0.9300
C7—H7	0.9300	C16—C17	1.388 (8)
C8—C9	1.446 (7)	C17—C18	1.376 (7)
C8—H8	0.9300	C17—H17	0.9300
C9—N1	1.310 (6)	C18—H18	0.9300
C9—S1	1.741 (5)	N1—N2	1.373 (5)
C10—N2	1.303 (6)	N3—H3A	0.8600
C10—N3	1.372 (6)
C6—C1—C2	121.0 (7)	N3—C11—C12	112.8 (4)
C6—C1—H1	119.5	O2—C12—C11	108.6 (4)
C2—C1—H1	119.5	O2—C12—H12A	110.0
C3—C2—C1	119.6 (8)	C11—C12—H12A	110.0
C3—C2—H2	120.2	O2—C12—H12B	110.0
C1—C2—H2	120.2	C11—C12—H12B	110.0
C4—C3—C2	120.9 (8)	H12A—C12—H12B	108.4
C4—C3—H3	119.6	O2—C13—C18	126.0 (5)
C2—C3—H3	119.6	O2—C13—C14	114.6 (4)
C3—C4—C5	119.8 (8)	C18—C13—C14	119.3 (5)
C3—C4—H4	120.1	C15—C14—C13	120.8 (5)
C5—C4—H4	120.1	C15—C14—H14	119.6
C4—C5—C6	121.1 (8)	C13—C14—H14	119.6
C4—C5—H5	119.4	C14—C15—C16	119.5 (5)
C6—C5—H5	119.4	C14—C15—H15	120.3
C1—C6—C5	117.6 (6)	C16—C15—H15	120.3
C1—C6—C7	123.5 (6)	C15—C16—C17	120.9 (5)
C5—C6—C7	118.9 (6)	C15—C16—Br1	119.3 (4)
C8—C7—C6	126.8 (6)	C17—C16—Br1	119.7 (4)
C8—C7—H7	116.6	C18—C17—C16	118.7 (5)
C6—C7—H7	116.6	C18—C17—H17	120.6
C7—C8—C9	125.5 (5)	C16—C17—H17	120.6
C7—C8—H8	117.3	C17—C18—C13	120.7 (5)
C9—C8—H8	117.3	C17—C18—H18	119.6
N1—C9—C8	122.4 (5)	C13—C18—H18	119.6
N1—C9—S1	113.6 (4)	C9—N1—N2	112.2 (4)
C8—C9—S1	123.9 (4)	C10—N2—N1	112.8 (4)
N2—C10—N3	120.9 (4)	C11—N3—C10	124.6 (4)
N2—C10—S1	114.6 (4)	C11—N3—H3A	117.7
N3—C10—S1	124.5 (4)	C10—N3—H3A	117.7
O1—C11—N3	122.2 (5)	C13—O2—C12	117.4 (4)
O1—C11—C12	125.0 (4)	C10—S1—C9	86.8 (2)
C6—C1—C2—C3	0.5 (12)	Br1—C16—C17—C18	−179.3 (4)
C1—C2—C3—C4	0.7 (13)	C16—C17—C18—C13	−0.8 (9)
C2—C3—C4—C5	−1.5 (14)	O2—C13—C18—C17	179.3 (5)
C3—C4—C5—C6	1.1 (12)	C14—C13—C18—C17	−1.0 (8)
C2—C1—C6—C5	−0.9 (10)	C8—C9—N1—N2	176.6 (5)
C2—C1—C6—C7	179.3 (6)	S1—C9—N1—N2	−0.5 (6)
C4—C5—C6—C1	0.1 (10)	N3—C10—N2—N1	179.2 (4)
C4—C5—C6—C7	179.9 (7)	S1—C10—N2—N1	−1.7 (6)
C1—C6—C7—C8	−3.0 (10)	C9—N1—N2—C10	1.4 (6)
C5—C6—C7—C8	177.2 (6)	O1—C11—N3—C10	−3.6 (8)
C6—C7—C8—C9	177.3 (5)	C12—C11—N3—C10	176.1 (5)
C7—C8—C9—N1	−175.0 (6)	N2—C10—N3—C11	177.2 (5)
C7—C8—C9—S1	1.8 (9)	S1—C10—N3—C11	−1.9 (7)
O1—C11—C12—O2	−4.8 (7)	C18—C13—O2—C12	3.0 (8)
N3—C11—C12—O2	175.5 (4)	C14—C13—O2—C12	−176.7 (5)
O2—C13—C14—C15	−178.9 (5)	C11—C12—O2—C13	−172.2 (4)
C18—C13—C14—C15	1.3 (8)	N2—C10—S1—C9	1.2 (4)
C13—C14—C15—C16	0.3 (9)	N3—C10—S1—C9	−179.7 (5)
C14—C15—C16—C17	−2.2 (9)	N1—C9—S1—C10	−0.4 (4)
C14—C15—C16—Br1	179.6 (4)	C8—C9—S1—C10	−177.4 (5)
C15—C16—C17—C18	2.5 (9)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
N3—H3A···N2^i	0.86	2.02	2.869 (6)	171
C14—H14···O1^ii	0.93	2.42	3.086 (6)	128

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