2-Ethyl-6-(4-methoxy­phen­yl)imidazo[2,1-b][1,3,4]thia­diazole-5-carbaldehyde

In the title compound, C₁₄H₁₃N₃O₂S, the imidazothia­diazole ring system and the methoxy­phenyl ring are not coplanar, having an angle of 31.60 (7)° between their mean planes. In the crystal structure, inter­molecular C—H...O hydrogen-bond inter­actions link the mol­ecules into dimers and π–π stacking inter­actions reinforce the crystal cohesion.

Key indicators

• Single-crystal X-ray study
• T = 293 K
• Mean [sigma](C-C) = 0.003 Å
• R factor = 0.036
• wR factor = 0.100
• Data-to-parameter ratio = 10.5

checkCIF/PLATON results

No syntax errors found



Alert level C
PLAT048_ALERT_1_C MoietyFormula Not Given ........................          ?
PLAT125_ALERT_4_C No _symmetry_space_group_name_Hall Given .......          ?
PLAT154_ALERT_1_C The su's on the Cell Angles are Equal (x 10000)         300 Deg.
PLAT322_ALERT_2_C Check Hybridisation of  S1     in Main Residue .          ?

Alert level G
PLAT199_ALERT_1_G Check the Reported _cell_measurement_temperature        293 K

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

   3 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
   1 ALERT type 2 Indicator that the structure model may be wrong or deficient
   0 ALERT type 3 Indicator that the structure quality may be low
   1 ALERT type 4 Improvement, methodology, query or suggestion
   0 ALERT type 5 Informative message, check

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Computing details

Data collection: SMART (Bruker, 1998); cell refinement: SAINT-Plus (Bruker, 1998); data reduction: SAINT-Plus; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997); software used to prepare material for publication: SHELXL97.

2-Ethyl-6-(4-methoxyphenyl)imidazo[2,1-b][1,3,4]thiadiazole-5-carbaldehyde

Crystal data

C14H13N3O2S	Z = 2
Mr = 287.33	F(000) = 300
Triclinic, P1	Dx = 1.43 Mg m^−3
a = 7.6931 (15) Å	Mo Kα radiation, λ = 0.71073 Å
b = 9.7197 (19) Å	Cell parameters from 15 reflections
c = 10.492 (2) Å	θ = 6.9–8.0°
α = 113.559 (3)°	µ = 0.25 mm^−1
β = 91.246 (3)°	T = 293 K
γ = 109.417 (3)°	Prism, white
V = 667.3 (2) Å^3	0.3 × 0.2 × 0.1 mm

Data collection

Bruker SMART CCD area-detector diffractometer	2124 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	Rint = 0.019
Graphite monochromator	θmax = 25.4°, θmin = 2.2°
φ and ω scans	h = −9→9
6646 measured reflections	k = −11→11
2439 independent reflections	l = −12→12

Refinement

Refinement on F^2	0 restraints
Least-squares matrix: full	All H-atom parameters refined
R[F^2 > 2σ(F^2)] = 0.036	w = 1/[σ^2(Fo^2) + (0.0621P)^2 + 0.1442P] where P = (Fo^2 + 2Fc^2)/3
wR(F^2) = 0.100	(Δ/σ)max < 0.001
S = 1.01	Δρmax = 0.19 e Å^−3
2439 reflections	Δρmin = −0.22 e Å^−3
233 parameters

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.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Ų)

	x	y	z	Uiso*/Ueq
C1	0.2096 (2)	0.5182 (2)	0.57853 (17)	0.0373 (4)
C2	0.0520 (2)	0.2930 (2)	0.63351 (18)	0.0380 (4)
C3	−0.0527 (3)	0.1857 (2)	0.6978 (2)	0.0437 (4)
C4	0.0136 (3)	0.2550 (3)	0.8563 (2)	0.0527 (5)
C5	0.2712 (2)	0.3865 (2)	0.36911 (17)	0.0374 (4)
C6	0.3313 (2)	0.5524 (2)	0.40864 (17)	0.0371 (4)
C7	0.3018 (3)	0.2582 (2)	0.2543 (2)	0.0480 (5)
C8	0.4117 (2)	0.6410 (2)	0.32566 (17)	0.0363 (4)
C9	0.3592 (3)	0.5692 (2)	0.17883 (19)	0.0429 (4)
C10	0.4256 (3)	0.6553 (2)	0.10190 (19)	0.0447 (4)
C11	0.5457 (3)	0.8159 (2)	0.16840 (19)	0.0422 (4)
C12	0.5980 (3)	0.8908 (2)	0.3150 (2)	0.0433 (4)
C13	0.5306 (2)	0.8023 (2)	0.39127 (19)	0.0401 (4)
C14	0.7187 (5)	1.0546 (3)	0.1422 (3)	0.0745 (8)
N1	0.18865 (19)	0.36878 (16)	0.48151 (14)	0.0366 (3)
N2	0.0984 (2)	0.23901 (17)	0.51017 (15)	0.0395 (3)
N3	0.2936 (2)	0.63371 (16)	0.53965 (14)	0.0390 (3)
O1	0.2443 (3)	0.11845 (17)	0.23374 (17)	0.0743 (5)
O2	0.6031 (2)	0.88749 (16)	0.08096 (14)	0.0594 (4)
S1	0.11720 (6)	0.50439 (5)	0.72283 (4)	0.04321 (17)
H3A	−0.044 (3)	0.083 (3)	0.647 (2)	0.051 (5)*
H3B	−0.185 (3)	0.166 (2)	0.677 (2)	0.057 (6)*
H4A	0.149 (4)	0.279 (3)	0.877 (3)	0.074 (7)*
H4B	−0.004 (3)	0.359 (3)	0.906 (2)	0.060 (6)*
H4C	−0.063 (3)	0.181 (3)	0.890 (3)	0.076 (7)*
H7	0.377 (3)	0.293 (2)	0.192 (2)	0.055 (6)*
H9	0.274 (3)	0.464 (2)	0.135 (2)	0.045 (5)*
H10	0.390 (3)	0.608 (2)	0.006 (2)	0.051 (5)*
H12	0.681 (3)	0.998 (3)	0.359 (2)	0.054 (6)*
H13	0.569 (3)	0.854 (2)	0.494 (2)	0.048 (5)*
H14A	0.837 (4)	1.070 (3)	0.192 (3)	0.090 (9)*
H14B	0.657 (4)	1.113 (3)	0.204 (3)	0.085 (9)*
H14C	0.731 (4)	1.078 (3)	0.066 (3)	0.092 (9)*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
C1	0.0399 (9)	0.0349 (9)	0.0323 (8)	0.0140 (7)	0.0045 (7)	0.0100 (7)
C2	0.0379 (9)	0.0358 (9)	0.0359 (9)	0.0125 (7)	0.0032 (7)	0.0125 (7)
C3	0.0453 (11)	0.0378 (10)	0.0421 (10)	0.0110 (8)	0.0090 (8)	0.0152 (8)
C4	0.0649 (14)	0.0492 (12)	0.0428 (11)	0.0186 (10)	0.0134 (10)	0.0206 (9)
C5	0.0422 (9)	0.0367 (9)	0.0318 (8)	0.0150 (7)	0.0074 (7)	0.0131 (7)
C6	0.0380 (9)	0.0369 (9)	0.0331 (8)	0.0139 (7)	0.0039 (7)	0.0119 (7)
C7	0.0605 (12)	0.0385 (10)	0.0431 (10)	0.0196 (9)	0.0158 (9)	0.0146 (8)
C8	0.0381 (9)	0.0360 (9)	0.0338 (8)	0.0155 (7)	0.0066 (7)	0.0127 (7)
C9	0.0477 (10)	0.0343 (9)	0.0374 (9)	0.0107 (8)	0.0035 (8)	0.0105 (8)
C10	0.0557 (11)	0.0434 (10)	0.0304 (9)	0.0184 (9)	0.0070 (8)	0.0116 (8)
C11	0.0497 (10)	0.0409 (9)	0.0415 (10)	0.0202 (8)	0.0163 (8)	0.0201 (8)
C12	0.0454 (10)	0.0341 (9)	0.0413 (10)	0.0093 (8)	0.0081 (8)	0.0119 (8)
C13	0.0429 (10)	0.0379 (9)	0.0337 (9)	0.0142 (8)	0.0051 (7)	0.0107 (8)
C14	0.104 (2)	0.0481 (13)	0.0642 (16)	0.0136 (14)	0.0283 (16)	0.0287 (12)
N1	0.0410 (8)	0.0313 (7)	0.0342 (7)	0.0129 (6)	0.0070 (6)	0.0113 (6)
N2	0.0425 (8)	0.0346 (7)	0.0389 (8)	0.0128 (6)	0.0076 (6)	0.0148 (6)
N3	0.0461 (8)	0.0340 (7)	0.0328 (7)	0.0136 (6)	0.0072 (6)	0.0116 (6)
O1	0.1111 (13)	0.0365 (8)	0.0660 (10)	0.0250 (8)	0.0404 (9)	0.0139 (7)
O2	0.0845 (10)	0.0463 (8)	0.0447 (7)	0.0173 (7)	0.0212 (7)	0.0224 (6)
S1	0.0532 (3)	0.0358 (3)	0.0341 (3)	0.0138 (2)	0.01124 (19)	0.01089 (19)

Geometric parameters (Å, º)

C1—N3	1.319 (2)	C7—H7	0.97 (2)
C1—N1	1.352 (2)	C8—C13	1.388 (2)
C1—S1	1.7210 (17)	C8—C9	1.396 (2)
C2—N2	1.296 (2)	C9—C10	1.374 (3)
C2—C3	1.490 (2)	C9—H9	0.92 (2)
C2—S1	1.7627 (17)	C10—C11	1.386 (3)
C3—C4	1.522 (3)	C10—H10	0.91 (2)
C3—H3A	0.95 (2)	C11—O2	1.358 (2)
C3—H3B	0.97 (2)	C11—C12	1.393 (3)
C4—H4A	0.99 (2)	C12—C13	1.386 (3)
C4—H4B	0.99 (2)	C12—H12	0.93 (2)
C4—H4C	0.96 (3)	C13—H13	0.98 (2)
C5—N1	1.395 (2)	C14—O2	1.422 (3)
C5—C6	1.395 (2)	C14—H14A	0.97 (3)
C5—C7	1.438 (2)	C14—H14B	0.93 (3)
C6—N3	1.378 (2)	C14—H14C	0.91 (3)
C6—C8	1.466 (2)	N1—N2	1.3760 (19)
C7—O1	1.204 (2)
N3—C1—N1	113.63 (15)	C9—C8—C6	120.84 (15)
N3—C1—S1	137.11 (13)	C10—C9—C8	120.86 (17)
N1—C1—S1	109.27 (12)	C10—C9—H9	120.7 (12)
N2—C2—C3	123.18 (16)	C8—C9—H9	118.4 (12)
N2—C2—S1	116.01 (13)	C9—C10—C11	120.72 (17)
C3—C2—S1	120.79 (13)	C9—C10—H10	120.4 (13)
C2—C3—C4	113.37 (16)	C11—C10—H10	118.9 (13)
C2—C3—H3A	106.8 (12)	O2—C11—C10	115.21 (16)
C4—C3—H3A	113.0 (12)	O2—C11—C12	125.37 (17)
C2—C3—H3B	107.7 (12)	C10—C11—C12	119.43 (16)
C4—C3—H3B	110.8 (12)	C13—C12—C11	119.26 (17)
H3A—C3—H3B	104.6 (17)	C13—C12—H12	121.5 (13)
C3—C4—H4A	110.2 (14)	C11—C12—H12	119.2 (13)
C3—C4—H4B	110.6 (12)	C12—C13—C8	121.79 (17)
H4A—C4—H4B	106.8 (19)	C12—C13—H13	119.2 (11)
C3—C4—H4C	108.5 (15)	C8—C13—H13	119.0 (11)
H4A—C4—H4C	113.9 (19)	O2—C14—H14A	109.2 (16)
H4B—C4—H4C	106.9 (19)	O2—C14—H14B	109.3 (18)
N1—C5—C6	103.46 (14)	H14A—C14—H14B	111 (2)
N1—C5—C7	124.01 (15)	O2—C14—H14C	103.2 (18)
C6—C5—C7	132.03 (16)	H14A—C14—H14C	113 (2)
N3—C6—C5	111.86 (15)	H14B—C14—H14C	111 (2)
N3—C6—C8	119.59 (14)	C1—N1—N2	118.32 (14)
C5—C6—C8	128.38 (15)	C1—N1—C5	107.24 (14)
O1—C7—C5	125.31 (18)	N2—N1—C5	134.45 (14)
O1—C7—H7	120.4 (12)	C2—N2—N1	108.23 (14)
C5—C7—H7	114.3 (12)	C1—N3—C6	103.77 (14)
C13—C8—C9	117.94 (16)	C11—O2—C14	118.35 (17)
C13—C8—C6	121.03 (15)	C1—S1—C2	88.14 (8)
N2—C2—C3—C4	141.56 (19)	N3—C1—N1—N2	−178.43 (13)
S1—C2—C3—C4	−39.4 (2)	S1—C1—N1—N2	1.79 (18)
N1—C5—C6—N3	1.77 (19)	N3—C1—N1—C5	1.86 (19)
C7—C5—C6—N3	−170.13 (19)	S1—C1—N1—C5	−177.91 (11)
N1—C5—C6—C8	−173.34 (15)	C6—C5—N1—C1	−2.10 (17)
C7—C5—C6—C8	14.8 (3)	C7—C5—N1—C1	170.65 (17)
N1—C5—C7—O1	7.8 (3)	C6—C5—N1—N2	178.26 (16)
C6—C5—C7—O1	178.3 (2)	C7—C5—N1—N2	−9.0 (3)
N3—C6—C8—C13	31.4 (2)	C3—C2—N2—N1	178.44 (15)
C5—C6—C8—C13	−153.78 (18)	S1—C2—N2—N1	−0.65 (18)
N3—C6—C8—C9	−143.40 (17)	C1—N1—N2—C2	−0.8 (2)
C5—C6—C8—C9	31.4 (3)	C5—N1—N2—C2	178.84 (17)
C13—C8—C9—C10	1.0 (3)	N1—C1—N3—C6	−0.72 (19)
C6—C8—C9—C10	175.95 (16)	S1—C1—N3—C6	178.97 (16)
C8—C9—C10—C11	−0.4 (3)	C5—C6—N3—C1	−0.72 (19)
C9—C10—C11—O2	179.39 (17)	C8—C6—N3—C1	174.87 (14)
C9—C10—C11—C12	−0.5 (3)	C10—C11—O2—C14	176.7 (2)
O2—C11—C12—C13	−179.09 (17)	C12—C11—O2—C14	−3.3 (3)
C10—C11—C12—C13	0.8 (3)	N3—C1—S1—C2	178.64 (19)
C11—C12—C13—C8	−0.2 (3)	N1—C1—S1—C2	−1.66 (12)
C9—C8—C13—C12	−0.7 (3)	N2—C2—S1—C1	1.39 (14)
C6—C8—C13—C12	−175.64 (16)	C3—C2—S1—C1	−177.72 (15)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
C4—H4C···O1^i	0.96 (3)	2.51 (3)	3.223 (2)	131

Symmetry code: (i) −x, −y, −z+1.