(E)-4-(Benzo[d]thiazol-2-yl)-N-(pyridin-3-ylmethylidene)aniline hemihydrate

The title compound, C₁₉H₁₃N₃S·0.5H₂O, is a benzo­thia­zole derivative that crystallized as a hemihydrate, the water O atom being situated on a twofold rotation axis. The dihedral angles between the central benzene ring and the benzo­thia­zole (r.m.s. deviation = 0.012 Å) and pyridine rings are 3.57 (6) and 10.12 (8)°, respectively, indicating that the mol­ecule is nearly planar. The conformation about the N=C bond is E. In the crystal, mol­ecules are linked by O_water—H...N_pyridine hydrogen bonds, forming dimers, which in turn are linked by C—H...O hydrogen bonds into layers parallel to the ab plane. The layers are linked by offset π–π inter­actions, forming a three-dimensional network [shortest inter­centroid distance = 3.721 (2) Å].

Key indicators

• Single-crystal X-ray study
• T = 296 K
• Mean [sigma](C-C) = 0.002 Å
• R factor = 0.034
• wR factor = 0.131
• Data-to-parameter ratio = 12.9

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
PLAT041_ALERT_1_C Calc. and Reported SumFormula    Strings  Differ     Please Check
PLAT147_ALERT_1_C s.u. on Symmetry Constrained Cell Angle(s) .....     Please Check
PLAT911_ALERT_3_C Missing # FCF Refl Between THmin & STh/L=  0.595          3 Report
PLAT918_ALERT_3_C Reflection(s) with I(obs) much Smaller I(calc) .          1 Check
PLAT934_ALERT_3_C Number of (Iobs-Icalc)/SigmaW > 10 Outliers ....          1 Check
PLAT939_ALERT_3_C Large Value of Not (SHELXL) Weight Optimized S .      10.64 Check

Alert level G
PLAT005_ALERT_5_G No Embedded Refinement Details found  in the CIF     Please Do !
PLAT042_ALERT_1_G Calc. and Reported MoietyFormula Strings  Differ     Please Check
PLAT045_ALERT_1_G Calculated and Reported Z Differ by a Factor ...       0.50 Check
PLAT066_ALERT_1_G Predicted and Reported Tmin&Tmax Range Identical          ? Check
PLAT128_ALERT_4_G Alternate Setting for Input Space Group     C2/c       I2/a Note
PLAT153_ALERT_1_G The s.u.'s on the Cell Axes   are Equal ..(Note)      0.005 Ang.
PLAT899_ALERT_4_G SHELXL97   is Deprecated and Succeeded by SHELXL       2014 Note
PLAT909_ALERT_3_G Percentage of Observed Data at Theta(Max) Still          76 %
PLAT978_ALERT_2_G Number C-C Bonds with Positive Residual Density           1 Note

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

   6 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
   6 ALERT type 3 Indicator that the structure quality may be low
   2 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, 2002); cell refinement: SAINT (Bruker, 2002); data reduction: SAINT (Bruker, 2002); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008) and Mercury (Macrae et al., 2008); software used to prepare material for publication: SHELXTL (Sheldrick, 2008).

(E)-4-(Benzo[d]thiazol-2-yl)-N-(pyridin-3-ylmethylidene)aniline hemihydrate

Crystal data

C19H13N3S·0.5H2O	F(000) = 1352
Mr = 324.39	Dx = 1.364 Mg m^−3
Monoclinic, C2/c	Mo Kα radiation, λ = 0.71069 Å
Hall symbol: -C 2yc	Cell parameters from 5584 reflections
a = 34.026 (5) Å	θ = 2.4–26.7°
b = 10.447 (5) Å	µ = 0.21 mm^−1
c = 8.967 (5) Å	T = 296 K
β = 97.601 (5)°	Block, yellow
V = 3159 (2) Å^3	0.23 × 0.22 × 0.21 mm
Z = 8

Data collection

Bruker SMART CCD area detector diffractometer	2794 independent reflections
Radiation source: fine-focus sealed tube	2444 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.019
phi and ω scans	θmax = 25.0°, θmin = 1.2°
Absorption correction: multi-scan (SADABS; Bruker, 2002)	h = −37→40
Tmin = 0.953, Tmax = 0.957	k = −12→12
11032 measured reflections	l = −10→10

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)] = 0.034	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.131	H atoms treated by a mixture of independent and constrained refinement
S = 1.09	w = 1/[σ^2(Fo^2) + (0.1P)^2] where P = (Fo^2 + 2Fc^2)/3
2794 reflections	(Δ/σ)max = 0.001
217 parameters	Δρmax = 0.19 e Å^−3
0 restraints	Δρmin = −0.23 e Å^−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.

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	0.640666 (11)	0.04206 (4)	0.17319 (4)	0.0537 (2)
N1	0.66886 (3)	0.21158 (11)	0.37023 (13)	0.0455 (3)
O1	1.0000	0.35524 (18)	0.2500	0.0718 (5)
C6	0.63000 (4)	0.18945 (13)	0.39216 (15)	0.0449 (3)
N2	0.83432 (4)	0.14991 (12)	0.10104 (14)	0.0518 (3)
C1	0.60952 (4)	0.09943 (13)	0.29545 (16)	0.0477 (4)
C7	0.67836 (4)	0.14078 (12)	0.26047 (15)	0.0424 (3)
C11	0.79462 (4)	0.14324 (13)	0.13047 (16)	0.0459 (4)
C16	0.89930 (5)	0.06086 (14)	−0.16991 (18)	0.0546 (4)
H16	0.8817	0.0151	−0.2382	0.066*
C15	0.88592 (4)	0.12279 (13)	−0.05054 (15)	0.0455 (4)
C14	0.84443 (4)	0.11634 (14)	−0.02344 (16)	0.0475 (4)
H14	0.8253	0.0870	−0.0993	0.057*
C8	0.71788 (4)	0.14141 (12)	0.21252 (15)	0.0420 (3)
C5	0.61062 (5)	0.24786 (15)	0.50285 (18)	0.0539 (4)
H5	0.6237	0.3079	0.5680	0.065*
C12	0.76579 (5)	0.06122 (15)	0.0601 (2)	0.0570 (4)
H12	0.7720	0.0063	−0.0150	0.068*
C13	0.72815 (5)	0.06029 (15)	0.10019 (18)	0.0546 (4)
H13	0.7092	0.0048	0.0517	0.066*
C10	0.78445 (5)	0.22285 (16)	0.24345 (18)	0.0564 (4)
H10	0.8035	0.2773	0.2932	0.068*
N3	0.95197 (4)	0.19941 (15)	0.02959 (16)	0.0677 (4)
C4	0.57205 (5)	0.21506 (17)	0.51363 (19)	0.0616 (4)
H4	0.5589	0.2539	0.5862	0.074*
C2	0.57032 (5)	0.06641 (16)	0.3070 (2)	0.0598 (4)
H2	0.5568	0.0070	0.2420	0.072*
C9	0.74685 (4)	0.22258 (15)	0.28291 (18)	0.0542 (4)
H9	0.7407	0.2776	0.3580	0.065*
C19	0.91367 (5)	0.19251 (15)	0.04519 (18)	0.0562 (4)
H19	0.9049	0.2368	0.1245	0.067*
C17	0.93888 (5)	0.06715 (17)	−0.1874 (2)	0.0655 (5)
H17	0.9484	0.0255	−0.2670	0.079*
C3	0.55236 (5)	0.12481 (17)	0.4178 (2)	0.0653 (5)
H3	0.5264	0.1032	0.4288	0.078*
C18	0.96381 (5)	0.13569 (17)	−0.0857 (2)	0.0670 (5)
H18	0.9906	0.1382	−0.0972	0.080*
H1	0.9871 (7)	0.300 (2)	0.188 (3)	0.107 (8)*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
S1	0.0521 (3)	0.0531 (3)	0.0567 (3)	−0.00853 (15)	0.0102 (2)	−0.01417 (16)
N1	0.0479 (7)	0.0446 (6)	0.0440 (7)	−0.0002 (5)	0.0058 (5)	−0.0019 (5)
O1	0.0611 (11)	0.0734 (12)	0.0771 (13)	0.000	−0.0049 (9)	0.000
C6	0.0478 (8)	0.0437 (7)	0.0428 (8)	0.0019 (6)	0.0043 (6)	0.0062 (6)
N2	0.0454 (7)	0.0584 (8)	0.0514 (8)	0.0014 (5)	0.0060 (6)	−0.0009 (6)
C1	0.0515 (9)	0.0448 (7)	0.0472 (8)	−0.0021 (6)	0.0078 (6)	0.0016 (6)
C7	0.0482 (8)	0.0392 (7)	0.0396 (7)	0.0012 (5)	0.0045 (6)	0.0029 (6)
C11	0.0445 (8)	0.0477 (8)	0.0446 (8)	0.0017 (6)	0.0029 (6)	0.0037 (6)
C16	0.0568 (10)	0.0552 (8)	0.0528 (9)	−0.0105 (7)	0.0105 (7)	−0.0033 (7)
C15	0.0474 (8)	0.0446 (7)	0.0438 (8)	−0.0009 (6)	0.0037 (6)	0.0086 (6)
C14	0.0451 (8)	0.0510 (8)	0.0450 (8)	−0.0007 (6)	0.0005 (6)	0.0045 (6)
C8	0.0459 (8)	0.0408 (7)	0.0385 (7)	0.0007 (5)	0.0027 (6)	0.0037 (5)
C5	0.0565 (9)	0.0563 (9)	0.0496 (9)	0.0048 (7)	0.0096 (7)	−0.0026 (7)
C12	0.0573 (10)	0.0568 (8)	0.0595 (9)	−0.0051 (7)	0.0170 (7)	−0.0154 (7)
C13	0.0513 (9)	0.0559 (8)	0.0576 (9)	−0.0098 (6)	0.0108 (7)	−0.0135 (7)
C10	0.0497 (9)	0.0625 (9)	0.0564 (9)	−0.0081 (7)	0.0043 (7)	−0.0131 (7)
N3	0.0520 (8)	0.0852 (10)	0.0645 (9)	−0.0153 (7)	0.0024 (7)	−0.0035 (8)
C4	0.0596 (10)	0.0702 (10)	0.0577 (10)	0.0102 (8)	0.0175 (8)	0.0050 (8)
C2	0.0514 (9)	0.0627 (9)	0.0658 (10)	−0.0098 (7)	0.0101 (8)	−0.0023 (8)
C9	0.0539 (9)	0.0579 (9)	0.0511 (9)	−0.0044 (7)	0.0084 (7)	−0.0143 (7)
C19	0.0537 (9)	0.0663 (9)	0.0481 (9)	−0.0056 (7)	0.0046 (7)	−0.0020 (7)
C17	0.0654 (11)	0.0642 (10)	0.0715 (12)	−0.0072 (8)	0.0259 (9)	−0.0082 (8)
C3	0.0517 (9)	0.0744 (11)	0.0721 (11)	−0.0022 (8)	0.0164 (8)	0.0085 (9)
C18	0.0498 (9)	0.0773 (11)	0.0761 (12)	−0.0068 (8)	0.0163 (9)	0.0017 (9)

Geometric parameters (Å, º)

S1—C1	1.7297 (16)	C8—C13	1.396 (2)
S1—C7	1.7482 (14)	C5—C4	1.372 (2)
N1—C7	1.3056 (18)	C5—H5	0.9300
N1—C6	1.3818 (19)	C12—C13	1.375 (2)
O1—H1	0.87 (2)	C12—H12	0.9300
C6—C1	1.401 (2)	C13—H13	0.9300
C6—C5	1.402 (2)	C10—C9	1.372 (2)
N2—C14	1.261 (2)	C10—H10	0.9300
N2—C11	1.4118 (18)	N3—C19	1.331 (2)
C1—C2	1.394 (2)	N3—C18	1.336 (2)
C7—C8	1.465 (2)	C4—C3	1.387 (3)
C11—C10	1.389 (2)	C4—H4	0.9300
C11—C12	1.389 (2)	C2—C3	1.377 (2)
C16—C17	1.378 (2)	C2—H2	0.9300
C16—C15	1.378 (2)	C9—H9	0.9300
C16—H16	0.9300	C19—H19	0.9300
C15—C19	1.394 (2)	C17—C18	1.364 (2)
C15—C14	1.465 (2)	C17—H17	0.9300
C14—H14	0.9300	C3—H3	0.9300
C8—C9	1.387 (2)	C18—H18	0.9300
C1—S1—C7	89.23 (7)	C13—C12—H12	119.6
C7—N1—C6	110.47 (12)	C11—C12—H12	119.6
N1—C6—C1	115.55 (12)	C12—C13—C8	120.99 (14)
N1—C6—C5	125.20 (13)	C12—C13—H13	119.5
C1—C6—C5	119.25 (13)	C8—C13—H13	119.5
C14—N2—C11	122.13 (12)	C9—C10—C11	121.16 (14)
C2—C1—C6	121.50 (14)	C9—C10—H10	119.4
C2—C1—S1	129.30 (13)	C11—C10—H10	119.4
C6—C1—S1	109.19 (11)	C19—N3—C18	117.01 (15)
N1—C7—C8	123.18 (12)	C5—C4—C3	120.96 (15)
N1—C7—S1	115.56 (11)	C5—C4—H4	119.5
C8—C7—S1	121.26 (10)	C3—C4—H4	119.5
C10—C11—C12	118.12 (14)	C3—C2—C1	117.67 (16)
C10—C11—N2	116.32 (13)	C3—C2—H2	121.2
C12—C11—N2	125.52 (13)	C1—C2—H2	121.2
C17—C16—C15	119.62 (15)	C10—C9—C8	120.97 (14)
C17—C16—H16	120.2	C10—C9—H9	119.5
C15—C16—H16	120.2	C8—C9—H9	119.5
C16—C15—C19	117.20 (14)	N3—C19—C15	123.79 (15)
C16—C15—C14	122.10 (13)	N3—C19—H19	118.1
C19—C15—C14	120.70 (13)	C15—C19—H19	118.1
N2—C14—C15	121.06 (13)	C18—C17—C16	118.65 (16)
N2—C14—H14	119.5	C18—C17—H17	120.7
C15—C14—H14	119.5	C16—C17—H17	120.7
C9—C8—C13	117.97 (14)	C2—C3—C4	121.61 (15)
C9—C8—C7	119.58 (13)	C2—C3—H3	119.2
C13—C8—C7	122.42 (12)	C4—C3—H3	119.2
C4—C5—C6	119.01 (15)	N3—C18—C17	123.70 (16)
C4—C5—H5	120.5	N3—C18—H18	118.2
C6—C5—H5	120.5	C17—C18—H18	118.2
C13—C12—C11	120.77 (14)
C7—N1—C6—C1	−0.22 (17)	N1—C6—C5—C4	−178.82 (13)
C7—N1—C6—C5	178.72 (13)	C1—C6—C5—C4	0.1 (2)
N1—C6—C1—C2	178.88 (13)	C10—C11—C12—C13	0.8 (2)
C5—C6—C1—C2	−0.1 (2)	N2—C11—C12—C13	178.31 (14)
N1—C6—C1—S1	−0.18 (16)	C11—C12—C13—C8	−0.1 (3)
C5—C6—C1—S1	−179.19 (11)	C9—C8—C13—C12	−0.3 (2)
C7—S1—C1—C2	−178.59 (16)	C7—C8—C13—C12	−178.52 (14)
C7—S1—C1—C6	0.39 (11)	C12—C11—C10—C9	−1.2 (2)
C6—N1—C7—C8	−178.89 (11)	N2—C11—C10—C9	−178.94 (13)
C6—N1—C7—S1	0.54 (15)	C6—C5—C4—C3	0.5 (2)
C1—S1—C7—N1	−0.56 (11)	C6—C1—C2—C3	−0.5 (2)
C1—S1—C7—C8	178.88 (11)	S1—C1—C2—C3	178.41 (12)
C14—N2—C11—C10	−157.22 (14)	C11—C10—C9—C8	0.9 (2)
C14—N2—C11—C12	25.2 (2)	C13—C8—C9—C10	−0.1 (2)
C17—C16—C15—C19	1.7 (2)	C7—C8—C9—C10	178.17 (14)
C17—C16—C15—C14	−178.10 (14)	C18—N3—C19—C15	0.4 (3)
C11—N2—C14—C15	−179.28 (12)	C16—C15—C19—N3	−1.8 (2)
C16—C15—C14—N2	164.97 (15)	C14—C15—C19—N3	178.03 (14)
C19—C15—C14—N2	−14.8 (2)	C15—C16—C17—C18	−0.4 (3)
N1—C7—C8—C9	−1.6 (2)	C1—C2—C3—C4	1.1 (3)
S1—C7—C8—C9	178.97 (11)	C5—C4—C3—C2	−1.2 (3)
N1—C7—C8—C13	176.59 (13)	C19—N3—C18—C17	1.1 (3)
S1—C7—C8—C13	−2.81 (19)	C16—C17—C18—N3	−1.2 (3)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
O1—H1···N3	0.88 (2)	2.03 (2)	2.894 (2)	170 (2)
C2—H2···O1^i	0.93	2.51	3.245 (3)	136

Symmetry code: (i) x−1/2, y−1/2, z.