The crystal structure of 6-(4-chloro­phen­yl)-2-(4-methyl­benz­yl)imidazo[2,1-b][1,3,4]thia­diazole-5-carbaldehyde

The title imidazo[2,1-b][1,3,4]thia­diazole derivative is non-planar, with the 4-methyl­benzyl and chloro­phenyl rings being inclined to the imidazo[2,1-b][1,3,4]thia­diazole ring system by 64.5 (1) and 3.7 (1)°, respectively.

Key indicators

• Single-crystal X-ray study
• T = 296 K
• Mean [sigma](C-C) = 0.003 Å
• R factor = 0.042
• wR factor = 0.110
• Data-to-parameter ratio = 13.0

checkCIF/PLATON results

No syntax errors found



Alert level B
PLAT919_ALERT_3_B Reflection # Likely Affected by the Beamstop ...          1 Check

Alert level C
PLAT029_ALERT_3_C _diffrn_measured_fraction_theta_full value Low .      0.977 Note
PLAT911_ALERT_3_C Missing # FCF Refl Between THmin & STh/L=  0.600         69 Report
PLAT934_ALERT_3_C Number of (Iobs-Icalc)/SigmaW > 10 Outliers ....          1 Check

Alert level G
PLAT432_ALERT_2_G Short Inter X...Y Contact  C12    ..  C19     ..       3.17 Ang.
PLAT882_ALERT_1_G Missing datum for _diffrn_reflns_av_unetI/netI .     Please Check
PLAT912_ALERT_4_G Missing # of FCF Reflections Above STh/L=  0.600          2 Note
PLAT913_ALERT_3_G Missing # of Very Strong Reflections in FCF ....          1 Note
PLAT954_ALERT_1_G Reported (CIF) and Actual (FCF) Kmax Differ by .          1 Units
PLAT955_ALERT_1_G Reported (CIF) and Actual (FCF) Lmax Differ by .          1 Units
PLAT961_ALERT_5_G Dataset Contains no Negative Intensities .......     Please Check
PLAT978_ALERT_2_G Number C-C Bonds with Positive Residual Density           7 Note

   0 ALERT level A = Most likely a serious problem - resolve or explain
   1 ALERT level B = A potentially serious problem, consider carefully
   3 ALERT level C = Check. Ensure it is not caused by an omission or oversight
   8 ALERT level G = General information/check it is not something unexpected

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

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Computing details

Data collection: SMART (Bruker, 2012); cell refinement: SAINT (Bruker, 2012); data reduction: SAINT (Bruker, 2012); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL2014 (Sheldrick, 2015); molecular graphics: ORTEP-3 for Windows (Farrugia, 2012), CAMERON (Watkin et al., 1996) and Mercury (Macrae et al., 2008); software used to prepare material for publication: WinGX (Farrugia, 2012) and PLATON (Spek, 2009).

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

Crystal data

C19H14ClN3OS	Z = 2
Mr = 367.84	F(000) = 380
Triclinic, P1	Dx = 1.492 Mg m^−3
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 5.6138 (18) Å	Cell parameters from 1890 reflections
b = 9.018 (2) Å	θ = 3.3–26.4°
c = 16.514 (5) Å	µ = 0.37 mm^−1
α = 80.533 (13)°	T = 296 K
β = 87.519 (14)°	Block, colourless
γ = 83.353 (14)°	0.20 × 0.15 × 0.10 mm
V = 818.9 (4) Å^3

Data collection

Bruker SMART CCD area-detector diffractometer	2966 independent reflections
Radiation source: fine-focus sealed tube	2530 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.059
ω and φ scans	θmax = 25.5°, θmin = 1.3°
Absorption correction: multi-scan (SADABS; Bruker, 2012)	h = −6→6
Tmin = 0.941, Tmax = 0.971	k = −11→11
12059 measured reflections	l = −20→20

Refinement

Refinement on F^2	Hydrogen site location: inferred from neighbouring sites
Least-squares matrix: full	H-atom parameters constrained
R[F^2 > 2σ(F^2)] = 0.042	w = 1/[σ^2(Fo^2) + (0.0537P)^2 + 0.289P] where P = (Fo^2 + 2Fc^2)/3
wR(F^2) = 0.110	(Δ/σ)max = 0.001
S = 1.05	Δρmax = 0.40 e Å^−3
2966 reflections	Δρmin = −0.26 e Å^−3
228 parameters	Extinction correction: SHELXL2014 (Sheldrick, 2015)
0 restraints	Extinction coefficient: 0.015 (3)

Special details

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.

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

	x	y	z	Uiso*/Ueq
S1	0.13628 (9)	0.55026 (6)	0.09398 (3)	0.01783 (18)
Cl1	0.76563 (10)	1.05603 (6)	−0.41113 (3)	0.02857 (19)
O1	−0.2181 (3)	1.11191 (15)	−0.14801 (9)	0.0188 (4)
N1	−0.2122 (3)	0.76902 (19)	0.06190 (10)	0.0169 (4)
N2	−0.0436 (3)	0.77957 (18)	−0.00135 (10)	0.0149 (4)
N3	0.3040 (3)	0.69994 (18)	−0.05952 (10)	0.0158 (4)
C1	0.2608 (4)	0.3316 (3)	0.48434 (13)	0.0254 (5)
H1A	0.3880	0.3909	0.4910	0.038*
H1B	0.3278	0.2319	0.4766	0.038*
H1C	0.1580	0.3249	0.5325	0.038*
C2	0.1165 (4)	0.4061 (2)	0.41000 (12)	0.0182 (5)
C3	−0.0867 (4)	0.3460 (2)	0.38955 (13)	0.0194 (5)
H3	−0.1379	0.2620	0.4234	0.023*
C4	−0.2144 (4)	0.4091 (2)	0.31943 (12)	0.0170 (5)
H4	−0.3490	0.3668	0.3070	0.020*
C5	−0.1425 (4)	0.5349 (2)	0.26779 (12)	0.0164 (5)
C6	0.0587 (4)	0.5973 (2)	0.28907 (13)	0.0187 (5)
H6	0.1082	0.6825	0.2559	0.022*
C7	0.1852 (4)	0.5335 (2)	0.35916 (13)	0.0183 (5)
H7	0.3182	0.5768	0.3722	0.022*
C8	−0.2861 (4)	0.6024 (2)	0.19192 (13)	0.0202 (5)
H8A	−0.3853	0.5279	0.1800	0.024*
H8B	−0.3928	0.6887	0.2045	0.024*
C9	−0.1409 (4)	0.6527 (2)	0.11621 (12)	0.0171 (5)
C10	0.1526 (4)	0.6762 (2)	0.00375 (12)	0.0159 (5)
C11	−0.0221 (4)	0.8823 (2)	−0.07365 (12)	0.0152 (4)
C12	−0.2119 (4)	1.0071 (2)	−0.09103 (13)	0.0174 (5)
H12	−0.3429	1.0065	−0.0545	0.021*
C13	0.1975 (4)	0.8283 (2)	−0.10865 (12)	0.0153 (5)
C14	0.3268 (4)	0.8852 (2)	−0.18484 (12)	0.0157 (4)
C15	0.2369 (4)	1.0111 (3)	−0.24086 (13)	0.0242 (5)
H15	0.0863	1.0608	−0.2313	0.029*
C16	0.3697 (4)	1.0622 (3)	−0.31028 (14)	0.0257 (5)
H16	0.3084	1.1459	−0.3471	0.031*
C17	0.5944 (4)	0.9882 (2)	−0.32487 (13)	0.0198 (5)
C18	0.6866 (4)	0.8621 (2)	−0.27129 (13)	0.0185 (5)
H18	0.8365	0.8122	−0.2816	0.022*
C19	0.5524 (4)	0.8117 (2)	−0.20223 (13)	0.0171 (5)
H19	0.6135	0.7266	−0.1663	0.021*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
S1	0.0166 (3)	0.0178 (3)	0.0168 (3)	0.0008 (2)	−0.0021 (2)	0.0024 (2)
Cl1	0.0260 (4)	0.0312 (3)	0.0236 (3)	0.0007 (2)	0.0075 (2)	0.0052 (2)
O1	0.0177 (8)	0.0161 (8)	0.0209 (8)	0.0003 (6)	−0.0028 (6)	0.0018 (6)
N1	0.0156 (10)	0.0195 (9)	0.0147 (9)	−0.0018 (7)	−0.0001 (7)	−0.0003 (7)
N2	0.0126 (10)	0.0169 (9)	0.0148 (9)	−0.0014 (7)	−0.0014 (7)	−0.0011 (7)
N3	0.0155 (10)	0.0146 (9)	0.0160 (9)	−0.0001 (7)	−0.0027 (7)	0.0002 (7)
C1	0.0276 (14)	0.0288 (12)	0.0171 (11)	0.0048 (10)	−0.0011 (10)	−0.0007 (9)
C2	0.0189 (12)	0.0200 (11)	0.0138 (10)	0.0065 (8)	0.0032 (9)	−0.0037 (8)
C3	0.0230 (13)	0.0156 (11)	0.0169 (11)	0.0009 (8)	0.0053 (9)	0.0013 (8)
C4	0.0155 (12)	0.0185 (11)	0.0171 (11)	−0.0013 (8)	0.0027 (9)	−0.0044 (8)
C5	0.0141 (12)	0.0188 (11)	0.0146 (10)	0.0026 (8)	0.0008 (8)	−0.0014 (8)
C6	0.0172 (12)	0.0172 (11)	0.0198 (11)	−0.0003 (8)	0.0041 (9)	0.0003 (9)
C7	0.0143 (12)	0.0217 (11)	0.0191 (11)	0.0002 (8)	0.0000 (9)	−0.0051 (9)
C8	0.0140 (12)	0.0238 (12)	0.0205 (11)	−0.0014 (8)	−0.0010 (9)	0.0026 (9)
C9	0.0148 (12)	0.0197 (11)	0.0169 (11)	−0.0012 (8)	−0.0045 (9)	−0.0024 (8)
C10	0.0151 (12)	0.0140 (10)	0.0183 (11)	−0.0002 (8)	−0.0033 (9)	−0.0022 (8)
C11	0.0162 (12)	0.0165 (10)	0.0123 (10)	−0.0026 (8)	−0.0017 (8)	0.0006 (8)
C12	0.0132 (12)	0.0197 (11)	0.0197 (11)	−0.0016 (8)	−0.0012 (9)	−0.0044 (9)
C13	0.0143 (11)	0.0153 (10)	0.0165 (11)	−0.0008 (8)	−0.0062 (8)	−0.0024 (8)
C14	0.0166 (12)	0.0156 (10)	0.0157 (10)	−0.0027 (8)	−0.0027 (8)	−0.0038 (8)
C15	0.0180 (13)	0.0289 (13)	0.0216 (12)	0.0060 (9)	0.0020 (9)	0.0015 (10)
C16	0.0210 (13)	0.0272 (12)	0.0227 (12)	0.0059 (9)	−0.0001 (10)	0.0079 (9)
C17	0.0212 (13)	0.0228 (11)	0.0149 (11)	−0.0023 (9)	0.0003 (9)	−0.0015 (9)
C18	0.0157 (12)	0.0181 (11)	0.0212 (11)	0.0027 (8)	0.0010 (9)	−0.0049 (9)
C19	0.0181 (12)	0.0133 (10)	0.0193 (11)	0.0007 (8)	−0.0033 (9)	−0.0017 (8)

Geometric parameters (Å, º)

S1—C10	1.724 (2)	C5—C8	1.521 (3)
S1—C9	1.772 (2)	C6—C7	1.390 (3)
Cl1—C17	1.749 (2)	C6—H6	0.9300
O1—C12	1.218 (2)	C7—H7	0.9300
N1—C9	1.299 (3)	C8—C9	1.498 (3)
N1—N2	1.378 (2)	C8—H8A	0.9700
N2—C10	1.355 (3)	C8—H8B	0.9700
N2—C11	1.395 (3)	C11—C13	1.408 (3)
N3—C10	1.323 (3)	C11—C12	1.458 (3)
N3—C13	1.389 (2)	C12—H12	0.9300
C1—C2	1.518 (3)	C13—C14	1.472 (3)
C1—H1A	0.9600	C14—C19	1.401 (3)
C1—H1B	0.9600	C14—C15	1.400 (3)
C1—H1C	0.9600	C15—C16	1.383 (3)
C2—C7	1.390 (3)	C15—H15	0.9300
C2—C3	1.395 (3)	C16—C17	1.388 (3)
C3—C4	1.393 (3)	C16—H16	0.9300
C3—H3	0.9300	C17—C18	1.384 (3)
C4—C5	1.391 (3)	C18—C19	1.382 (3)
C4—H4	0.9300	C18—H18	0.9300
C5—C6	1.401 (3)	C19—H19	0.9300
C10—S1—C9	87.97 (10)	H8A—C8—H8B	107.5
C9—N1—N2	108.08 (16)	N1—C9—C8	122.86 (19)
C10—N2—N1	118.52 (17)	N1—C9—S1	116.07 (16)
C10—N2—C11	108.08 (17)	C8—C9—S1	121.03 (15)
N1—N2—C11	133.36 (17)	N3—C10—N2	113.00 (18)
C10—N3—C13	104.36 (16)	N3—C10—S1	137.61 (15)
C2—C1—H1A	109.5	N2—C10—S1	109.37 (15)
C2—C1—H1B	109.5	N2—C11—C13	103.37 (17)
H1A—C1—H1B	109.5	N2—C11—C12	117.73 (19)
C2—C1—H1C	109.5	C13—C11—C12	138.89 (19)
H1A—C1—H1C	109.5	O1—C12—C11	127.2 (2)
H1B—C1—H1C	109.5	O1—C12—H12	116.4
C7—C2—C3	117.96 (19)	C11—C12—H12	116.4
C7—C2—C1	121.3 (2)	N3—C13—C11	111.17 (18)
C3—C2—C1	120.7 (2)	N3—C13—C14	117.41 (18)
C2—C3—C4	121.3 (2)	C11—C13—C14	131.42 (18)
C2—C3—H3	119.4	C19—C14—C15	117.89 (19)
C4—C3—H3	119.4	C19—C14—C13	118.83 (18)
C5—C4—C3	120.6 (2)	C15—C14—C13	123.27 (19)
C5—C4—H4	119.7	C16—C15—C14	120.7 (2)
C3—C4—H4	119.7	C16—C15—H15	119.6
C4—C5—C6	118.18 (19)	C14—C15—H15	119.6
C4—C5—C8	119.60 (19)	C15—C16—C17	119.9 (2)
C6—C5—C8	122.20 (19)	C15—C16—H16	120.1
C7—C6—C5	120.8 (2)	C17—C16—H16	120.1
C7—C6—H6	119.6	C18—C17—C16	120.8 (2)
C5—C6—H6	119.6	C18—C17—Cl1	119.38 (17)
C2—C7—C6	121.1 (2)	C16—C17—Cl1	119.84 (16)
C2—C7—H7	119.4	C19—C18—C17	118.9 (2)
C6—C7—H7	119.4	C19—C18—H18	120.5
C9—C8—C5	115.50 (18)	C17—C18—H18	120.5
C9—C8—H8A	108.4	C18—C19—C14	121.79 (19)
C5—C8—H8A	108.4	C18—C19—H19	119.1
C9—C8—H8B	108.4	C14—C19—H19	119.1
C5—C8—H8B	108.4
C9—N1—N2—C10	−0.5 (2)	C9—S1—C10—N2	−0.02 (15)
C9—N1—N2—C11	−177.9 (2)	C10—N2—C11—C13	0.5 (2)
C7—C2—C3—C4	1.4 (3)	N1—N2—C11—C13	178.12 (18)
C1—C2—C3—C4	−177.03 (18)	C10—N2—C11—C12	−178.46 (17)
C2—C3—C4—C5	−0.2 (3)	N1—N2—C11—C12	−0.9 (3)
C3—C4—C5—C6	−1.1 (3)	N2—C11—C12—O1	175.43 (19)
C3—C4—C5—C8	−179.56 (19)	C13—C11—C12—O1	−3.1 (4)
C4—C5—C6—C7	1.1 (3)	C10—N3—C13—C11	0.1 (2)
C8—C5—C6—C7	179.56 (19)	C10—N3—C13—C14	179.35 (17)
C3—C2—C7—C6	−1.4 (3)	N2—C11—C13—N3	−0.4 (2)
C1—C2—C7—C6	177.07 (19)	C12—C11—C13—N3	178.2 (2)
C5—C6—C7—C2	0.1 (3)	N2—C11—C13—C14	−179.49 (19)
C4—C5—C8—C9	−139.6 (2)	C12—C11—C13—C14	−0.8 (4)
C6—C5—C8—C9	41.9 (3)	N3—C13—C14—C19	−2.5 (3)
N2—N1—C9—C8	−177.12 (17)	C11—C13—C14—C19	176.5 (2)
N2—N1—C9—S1	0.5 (2)	N3—C13—C14—C15	178.33 (18)
C5—C8—C9—N1	−146.1 (2)	C11—C13—C14—C15	−2.7 (3)
C5—C8—C9—S1	36.4 (3)	C19—C14—C15—C16	−1.1 (3)
C10—S1—C9—N1	−0.27 (17)	C13—C14—C15—C16	178.0 (2)
C10—S1—C9—C8	177.37 (18)	C14—C15—C16—C17	0.0 (4)
C13—N3—C10—N2	0.2 (2)	C15—C16—C17—C18	0.9 (3)
C13—N3—C10—S1	−178.12 (18)	C15—C16—C17—Cl1	−178.23 (18)
N1—N2—C10—N3	−178.50 (16)	C16—C17—C18—C19	−0.8 (3)
C11—N2—C10—N3	−0.5 (2)	Cl1—C17—C18—C19	178.40 (15)
N1—N2—C10—S1	0.3 (2)	C17—C18—C19—C14	−0.4 (3)
C11—N2—C10—S1	178.32 (13)	C15—C14—C19—C18	1.3 (3)
C9—S1—C10—N3	178.4 (2)	C13—C14—C19—C18	−177.90 (18)

Hydrogen-bond geometry (Å, º)

Cg is the centroid of the C2–C7 ring.

D—H···A	D—H	H···A	D···A	D—H···A
C15—H15···O1	0.93	2.20	3.047 (3)	151
C19—H19···N3	0.93	2.42	2.788 (3)	103
C19—H19···S1^i	0.93	2.83	3.733 (2)	165
C6—H6···O1^ii	0.93	2.46	3.384 (3)	170
C18—H18···Cg^i	0.93	2.92	3.648 (12)	136

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