2,3-Di­hydro­benz[4,5]imidazo[2,1-b]thia­zole

The asymmetric unit of the title compound, C₉H₈N₂S, consists of two independent mol­ecules (A and B) differing in the conformation of the thia­zole ring: twisted for mol­ecule A and planar for mol­ecule B. In the crystal, mol­ecules stack along the c axis in alternating A and B layers. Within the layers, mol­ecules are linked by C—H...π inter­actions, and inversion-related B mol­ecules are linked by offset π–π inter­actions [inter-centroid distance = 3.716 (1) Å]. The two mol­ecules are also linked by a C—H...N hydrogen bond, which results finally in the formation of a three-dimensional structure.

Key indicators

• Single-crystal X-ray study
• T = 298 K
• Mean [sigma](C-C) = 0.003 Å
• R factor = 0.046
• wR factor = 0.134
• Data-to-parameter ratio = 15.1

checkCIF/PLATON results

No syntax errors found



Alert level C
PLAT241_ALERT_2_C High   'MainMol' Ueq as Compared to Neighbors of        C18 Check
PLAT906_ALERT_3_C Large K value in the Analysis of Variance ......      2.487 Check

Alert level G
PLAT912_ALERT_4_G Missing # of FCF Reflections Above STh/L=  0.600        219 Note
PLAT978_ALERT_2_G Number C-C Bonds with Positive Residual Density.          5 Note

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

   0 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
   1 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: APEX3 (Bruker, 2016); cell refinement: SAINT (Bruker, 2016); data reduction: SAINT (Bruker, 2016); program(s) used to solve structure: SHELXT (Sheldrick, 2015a); program(s) used to refine structure: SHELXL2014 (Sheldrick, 2015b); molecular graphics: DIAMOND (Brandenburg & Putz, 2012 and Mercury (Macrae et al., 2008); software used to prepare material for publication: SHELXTL (Sheldrick, 2008).

2,3-Dihydrobenz[4,5]imidazo[2,1-b]thiazole

Crystal data

C9H8N2S	F(000) = 736
Mr = 176.23	Dx = 1.411 Mg m^−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
a = 12.7440 (8) Å	Cell parameters from 4421 reflections
b = 11.4820 (7) Å	θ = 2.5–25.4°
c = 12.8707 (8) Å	µ = 0.33 mm^−1
β = 118.234 (1)°	T = 298 K
V = 1659.25 (18) Å^3	Plate, colourless
Z = 8	0.38 × 0.22 × 0.06 mm

Data collection

Bruker SMART APEX CCD diffractometer	4244 independent reflections
Radiation source: fine-focus sealed tube	2702 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.036
Detector resolution: 8.3333 pixels mm^-1	θmax = 29.1°, θmin = 1.8°
φ and ω scans	h = −17→17
Absorption correction: multi-scan (SADABS; Bruker, 2016)	k = −15→15
Tmin = 0.87, Tmax = 0.98	l = −16→17
15538 measured reflections

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)] = 0.046	Hydrogen site location: difference Fourier map
wR(F^2) = 0.134	All H-atom parameters refined
S = 1.02	w = 1/[σ^2(Fo^2) + (0.0762P)^2] where P = (Fo^2 + 2Fc^2)/3
4244 reflections	(Δ/σ)max = 0.001
281 parameters	Δρmax = 0.27 e Å^−3
0 restraints	Δρmin = −0.25 e Å^−3

Special details

Experimental. The diffraction data were collected in three sets of 363 frames (0.5° width in ω) at φ = 0, 120 and 240°. A scan time of 40 sec/frame was used.

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 (Ų)

	x	y	z	Uiso*/Ueq
S1	0.60928 (5)	0.83270 (4)	0.50755 (5)	0.06186 (19)
N1	0.67791 (13)	0.67804 (12)	0.69522 (13)	0.0494 (4)
N2	0.48777 (12)	0.67647 (11)	0.55018 (12)	0.0423 (3)
C1	0.61392 (15)	0.59028 (14)	0.71572 (15)	0.0433 (4)
C2	0.65137 (19)	0.51054 (16)	0.80769 (17)	0.0530 (5)
H2	0.7323 (17)	0.5100 (17)	0.8657 (17)	0.067 (6)*
C3	0.5701 (2)	0.43030 (17)	0.80575 (18)	0.0571 (5)
H3	0.5961 (19)	0.375 (2)	0.8645 (19)	0.076 (6)*
C4	0.4535 (2)	0.42874 (17)	0.71608 (19)	0.0585 (5)
H4	0.3984 (17)	0.3748 (19)	0.7162 (17)	0.067 (6)*
C5	0.41276 (17)	0.50738 (16)	0.62405 (17)	0.0503 (4)
H5	0.3330 (18)	0.5108 (18)	0.5642 (16)	0.064 (6)*
C6	0.49469 (14)	0.58756 (13)	0.62549 (14)	0.0408 (4)
C7	0.59884 (15)	0.72369 (15)	0.59596 (15)	0.0442 (4)
C8	0.40008 (17)	0.71382 (17)	0.43372 (16)	0.0489 (4)
H8A	0.3903 (15)	0.6550 (16)	0.3759 (15)	0.047 (5)*
H8B	0.3277 (17)	0.7257 (16)	0.4307 (15)	0.054 (5)*
C9	0.4497 (2)	0.8251 (2)	0.4088 (2)	0.0637 (6)
H9A	0.435 (2)	0.8278 (18)	0.330 (2)	0.080 (7)*
H9B	0.4210 (19)	0.895 (2)	0.4243 (19)	0.084 (8)*
S2	0.09273 (5)	0.81657 (5)	0.59932 (5)	0.06511 (19)
N3	0.14754 (13)	0.66410 (13)	0.46357 (14)	0.0531 (4)
N4	−0.03893 (13)	0.66826 (12)	0.43993 (13)	0.0447 (3)
C10	0.07636 (16)	0.58368 (15)	0.37754 (16)	0.0480 (4)
C11	0.1060 (2)	0.50724 (18)	0.31224 (19)	0.0605 (5)
H11	0.1862 (18)	0.5015 (17)	0.3240 (16)	0.066 (6)*
C12	0.0190 (2)	0.43527 (18)	0.2334 (2)	0.0686 (6)
H12	0.0374 (18)	0.384 (2)	0.1871 (18)	0.073 (6)*
C13	−0.0963 (2)	0.43830 (19)	0.2175 (2)	0.0716 (6)
H13	−0.152 (2)	0.389 (2)	0.166 (2)	0.091 (8)*
C14	−0.12870 (19)	0.51306 (18)	0.28185 (18)	0.0591 (5)
H14	−0.203 (2)	0.512 (2)	0.2730 (19)	0.084 (7)*
C15	−0.04071 (15)	0.58468 (14)	0.36185 (15)	0.0442 (4)
C16	0.07387 (15)	0.71029 (15)	0.49625 (15)	0.0469 (4)
C17	−0.12433 (18)	0.71370 (19)	0.47270 (19)	0.0520 (5)
H17A	−0.1465 (16)	0.6577 (16)	0.5092 (16)	0.053 (5)*
H17B	−0.1870 (19)	0.740 (2)	0.4091 (19)	0.075 (7)*
C18	−0.0634 (2)	0.8086 (3)	0.5617 (3)	0.0783 (7)
H18A	−0.070 (3)	0.805 (3)	0.625 (3)	0.131 (13)*
H18B	−0.094 (3)	0.885 (3)	0.530 (3)	0.140 (13)*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
S1	0.0674 (4)	0.0543 (3)	0.0757 (4)	−0.0089 (2)	0.0435 (3)	0.0056 (2)
N1	0.0439 (8)	0.0468 (8)	0.0566 (9)	−0.0006 (6)	0.0230 (8)	−0.0052 (7)
N2	0.0413 (8)	0.0416 (8)	0.0472 (8)	−0.0001 (6)	0.0235 (7)	0.0012 (6)
C1	0.0447 (10)	0.0410 (8)	0.0463 (9)	0.0037 (7)	0.0234 (8)	−0.0053 (7)
C2	0.0562 (12)	0.0519 (11)	0.0466 (10)	0.0112 (9)	0.0208 (9)	−0.0023 (8)
C3	0.0768 (15)	0.0488 (11)	0.0510 (11)	0.0088 (10)	0.0347 (11)	0.0075 (9)
C4	0.0698 (14)	0.0514 (11)	0.0667 (13)	−0.0033 (10)	0.0425 (12)	0.0069 (9)
C5	0.0467 (11)	0.0521 (10)	0.0566 (11)	−0.0026 (8)	0.0282 (9)	0.0031 (9)
C6	0.0442 (9)	0.0388 (8)	0.0444 (9)	0.0026 (7)	0.0250 (8)	−0.0015 (7)
C7	0.0458 (10)	0.0389 (9)	0.0549 (11)	−0.0022 (7)	0.0295 (9)	−0.0065 (7)
C8	0.0495 (11)	0.0529 (11)	0.0459 (10)	0.0042 (9)	0.0238 (9)	0.0050 (9)
C9	0.0703 (15)	0.0566 (13)	0.0652 (14)	0.0022 (10)	0.0329 (12)	0.0119 (10)
S2	0.0623 (4)	0.0667 (4)	0.0651 (4)	−0.0156 (2)	0.0291 (3)	−0.0188 (2)
N3	0.0410 (9)	0.0622 (10)	0.0572 (9)	−0.0010 (7)	0.0242 (8)	−0.0005 (7)
N4	0.0386 (8)	0.0468 (8)	0.0481 (8)	0.0000 (6)	0.0200 (7)	−0.0020 (6)
C10	0.0489 (10)	0.0487 (10)	0.0493 (10)	0.0088 (8)	0.0255 (9)	0.0107 (8)
C11	0.0673 (14)	0.0630 (12)	0.0626 (13)	0.0156 (11)	0.0400 (12)	0.0100 (10)
C12	0.0960 (18)	0.0571 (12)	0.0657 (14)	0.0089 (12)	0.0487 (14)	−0.0015 (11)
C13	0.0914 (18)	0.0595 (13)	0.0663 (14)	−0.0141 (12)	0.0393 (14)	−0.0150 (11)
C14	0.0571 (13)	0.0608 (12)	0.0614 (12)	−0.0111 (10)	0.0297 (11)	−0.0076 (10)
C15	0.0477 (10)	0.0408 (8)	0.0465 (9)	0.0007 (7)	0.0242 (8)	0.0027 (7)
C16	0.0427 (10)	0.0480 (9)	0.0467 (10)	−0.0032 (8)	0.0184 (8)	0.0017 (8)
C17	0.0496 (11)	0.0583 (11)	0.0543 (12)	0.0018 (9)	0.0298 (10)	0.0017 (10)
C18	0.0618 (14)	0.0847 (18)	0.0860 (18)	0.0015 (13)	0.0330 (14)	−0.0303 (15)

Geometric parameters (Å, º)

S1—C7	1.7385 (18)	S2—C16	1.7336 (18)
S1—C9	1.821 (3)	S2—C18	1.813 (3)
N1—C7	1.305 (2)	N3—C16	1.309 (2)
N1—C1	1.398 (2)	N3—C10	1.397 (2)
N2—C7	1.362 (2)	N4—C16	1.356 (2)
N2—C6	1.381 (2)	N4—C15	1.382 (2)
N2—C8	1.447 (2)	N4—C17	1.438 (2)
C1—C2	1.390 (3)	C10—C11	1.385 (3)
C1—C6	1.410 (2)	C10—C15	1.408 (2)
C2—C3	1.378 (3)	C11—C12	1.370 (3)
C2—H2	0.945 (19)	C11—H11	0.961 (19)
C3—C4	1.384 (3)	C12—C13	1.385 (3)
C3—H3	0.92 (2)	C12—H12	0.94 (2)
C4—C5	1.381 (3)	C13—C14	1.385 (3)
C4—H4	0.94 (2)	C13—H13	0.90 (2)
C5—C6	1.386 (2)	C14—C15	1.379 (3)
C5—H5	0.942 (19)	C14—H14	0.90 (2)
C8—C9	1.525 (3)	C17—C18	1.503 (3)
C8—H8A	0.968 (18)	C17—H17A	0.917 (19)
C8—H8B	0.915 (19)	C17—H17B	0.88 (2)
C9—H9A	0.94 (2)	C18—H18A	0.85 (3)
C9—H9B	0.94 (2)	C18—H18B	0.97 (3)
C7—S1—C9	90.94 (9)	C16—S2—C18	91.29 (10)
C7—N1—C1	103.00 (14)	C16—N3—C10	103.12 (14)
C7—N2—C6	106.40 (14)	C16—N4—C15	106.52 (14)
C7—N2—C8	117.73 (14)	C16—N4—C17	118.16 (15)
C6—N2—C8	135.01 (15)	C15—N4—C17	135.30 (15)
C2—C1—N1	129.76 (17)	C11—C10—N3	129.68 (18)
C2—C1—C6	119.26 (17)	C11—C10—C15	119.51 (18)
N1—C1—C6	110.98 (15)	N3—C10—C15	110.80 (15)
C3—C2—C1	118.20 (19)	C12—C11—C10	118.3 (2)
C3—C2—H2	122.7 (12)	C12—C11—H11	120.2 (12)
C1—C2—H2	119.0 (12)	C10—C11—H11	121.5 (12)
C2—C3—C4	121.65 (19)	C11—C12—C13	121.7 (2)
C2—C3—H3	118.0 (14)	C11—C12—H12	119.2 (13)
C4—C3—H3	120.3 (14)	C13—C12—H12	119.1 (13)
C5—C4—C3	121.78 (19)	C12—C13—C14	121.5 (2)
C5—C4—H4	117.1 (13)	C12—C13—H13	119.9 (17)
C3—C4—H4	121.1 (13)	C14—C13—H13	118.5 (17)
C4—C5—C6	116.60 (18)	C15—C14—C13	116.7 (2)
C4—C5—H5	123.5 (12)	C15—C14—H14	122.5 (15)
C6—C5—H5	119.8 (12)	C13—C14—H14	120.7 (15)
N2—C6—C5	133.16 (16)	C14—C15—N4	133.23 (17)
N2—C6—C1	104.34 (14)	C14—C15—C10	122.31 (17)
C5—C6—C1	122.50 (16)	N4—C15—C10	104.46 (15)
N1—C7—N2	115.25 (15)	N3—C16—N4	115.10 (16)
N1—C7—S1	131.83 (14)	N3—C16—S2	132.09 (14)
N2—C7—S1	112.90 (13)	N4—C16—S2	112.81 (13)
N2—C8—C9	105.81 (16)	N4—C17—C18	107.23 (17)
N2—C8—H8A	110.2 (11)	N4—C17—H17A	110.8 (12)
C9—C8—H8A	109.8 (10)	C18—C17—H17A	107.0 (12)
N2—C8—H8B	110.9 (11)	N4—C17—H17B	109.3 (14)
C9—C8—H8B	112.1 (12)	C18—C17—H17B	111.7 (15)
H8A—C8—H8B	108.1 (15)	H17A—C17—H17B	110.8 (18)
C8—C9—S1	109.29 (15)	C17—C18—S2	110.27 (16)
C8—C9—H9A	111.2 (14)	C17—C18—H18A	116 (2)
S1—C9—H9A	109.9 (14)	S2—C18—H18A	109 (2)
C8—C9—H9B	115.4 (14)	C17—C18—H18B	112 (2)
S1—C9—H9B	103.2 (13)	S2—C18—H18B	104.2 (19)
H9A—C9—H9B	107.5 (19)	H18A—C18—H18B	104 (3)
C7—N1—C1—C2	179.00 (17)	C16—N3—C10—C11	−178.96 (19)
C7—N1—C1—C6	−0.63 (17)	C16—N3—C10—C15	−0.18 (19)
N1—C1—C2—C3	−178.60 (17)	N3—C10—C11—C12	179.12 (18)
C6—C1—C2—C3	1.0 (2)	C15—C10—C11—C12	0.4 (3)
C1—C2—C3—C4	−0.8 (3)	C10—C11—C12—C13	0.5 (3)
C2—C3—C4—C5	0.0 (3)	C11—C12—C13—C14	−1.0 (4)
C3—C4—C5—C6	0.4 (3)	C12—C13—C14—C15	0.4 (3)
C7—N2—C6—C5	−178.18 (18)	C13—C14—C15—N4	−179.87 (19)
C8—N2—C6—C5	−9.5 (3)	C13—C14—C15—C10	0.6 (3)
C7—N2—C6—C1	1.27 (16)	C16—N4—C15—C14	180.0 (2)
C8—N2—C6—C1	169.95 (17)	C17—N4—C15—C14	1.7 (3)
C4—C5—C6—N2	179.21 (17)	C16—N4—C15—C10	−0.44 (18)
C4—C5—C6—C1	−0.2 (3)	C17—N4—C15—C10	−178.74 (19)
C2—C1—C6—N2	179.90 (14)	C11—C10—C15—C14	−1.0 (3)
N1—C1—C6—N2	−0.42 (17)	N3—C10—C15—C14	−179.95 (17)
C2—C1—C6—C5	−0.6 (2)	C11—C10—C15—N4	179.32 (16)
N1—C1—C6—C5	179.10 (15)	N3—C10—C15—N4	0.40 (18)
C1—N1—C7—N2	1.54 (18)	C10—N3—C16—N4	−0.1 (2)
C1—N1—C7—S1	−176.53 (14)	C10—N3—C16—S2	179.86 (15)
C6—N2—C7—N1	−1.88 (19)	C15—N4—C16—N3	0.4 (2)
C8—N2—C7—N1	−172.86 (15)	C17—N4—C16—N3	179.02 (16)
C6—N2—C7—S1	176.57 (11)	C15—N4—C16—S2	−179.61 (11)
C8—N2—C7—S1	5.59 (19)	C17—N4—C16—S2	−1.0 (2)
C9—S1—C7—N1	−176.19 (18)	C18—S2—C16—N3	178.1 (2)
C9—S1—C7—N2	5.70 (14)	C18—S2—C16—N4	−1.92 (17)
C7—N2—C8—C9	−16.1 (2)	C16—N4—C17—C18	4.0 (3)
C6—N2—C8—C9	176.18 (18)	C15—N4—C17—C18	−177.8 (2)
N2—C8—C9—S1	18.9 (2)	N4—C17—C18—S2	−5.1 (3)
C7—S1—C9—C8	−14.46 (17)	C16—S2—C18—C17	4.1 (2)

Hydrogen-bond geometry (Å, º)

Cg3, Cg7 and Cg9 are the centroids of the C1–C6, S2/N4/C16–C18 and C10–C15 rings, respectively.

D—H···A	D—H	H···A	D···A	D—H···A
C8—H8B···N3	0.92 (2)	2.62 (2)	3.464 (2)	154 (2)
C8—H8A···Cg3^i	0.97 (2)	2.65 (2)	3.543 (2)	154 (2)
C9—H9A···Cg3^ii	0.94 (2)	2.99 (2)	3.661 (3)	129 (2)
C12—H12···Cg7^iii	0.94 (2)	2.94 (2)	3.838 (2)	161 (2)
C18—H18A···Cg9^iv	0.85 (3)	2.90 (3)	3.471 (4)	126 (3)

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