N,N-(2-benzo­thia­zole)(2-pyridyl­methyl)amine

The crystal structure of a new compound, N,N-(2-benzo­thia­zole)(2-pyridyl­methyl)­amine C₁₃H₁₁N₃S, has been determined by X-ray diffraction analysis. The amino group and the pyridine-N atom are involved in intermolecular hydrogen bonds, which link the mol­ecules into one-dimensional chains.

Key indicators

• Single-crystal X-ray study
• T = 296 K
• Mean [sigma](C-C) = 0.005 Å
• R factor = 0.031
• wR factor = 0.070
• Data-to-parameter ratio = 8.5

checkCIF/PLATON results

No syntax errors found



Alert level C
PLAT034_ALERT_1_C No Flack Parameter Given. Z .GT. Si, NonCentro .          ?
PLAT322_ALERT_2_C Check Hybridisation of  S      in Main Residue .          ?

Alert level G
REFLT03_ALERT_4_G  WARNING: Large fraction of Friedel related reflns may
                     be needed to determine absolute structure
           From the CIF: _diffrn_reflns_theta_max           26.99
           From the CIF: _reflns_number_total               1317
           Count of symmetry unique reflns         1316
           Completeness (_total/calc)            100.08%
           TEST3: Check Friedels for noncentro structure
           Estimate of Friedel pairs measured         1
           Fraction of Friedel pairs measured     0.001
           Are heavy atom types Z>Si present          yes

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

   1 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

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Computing details

Data collection: XSCANS (Siemens, 1994); cell refinement: XSCANS; data reduction: SHELXTL (Sheldrick, 1997a); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997b); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997b); molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL.

N,N-(2-bezothiazole)(2-pyridylmethyl)amine

Crystal data

C13H11N3S	F(000) = 1008
Mr = 241.31	Dx = 1.405 Mg m^−3
Orthorhombic, Iba2	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: I2-2c	Cell parameters from 36 reflections
a = 20.144 (4) Å	θ = 4.0–15.3°
b = 9.774 (2) Å	µ = 0.26 mm^−1
c = 11.586 (1) Å	T = 296 K
V = 2281.1 (7) Å^3	Prism, pale-yellow
Z = 8	0.52 × 0.44 × 0.44 mm

Data collection

Siemens P4 diffractometer	1107 reflections with I > 2σ(I)
Radiation source: normal-focus sealed tube	Rint = 0.011
Graphite monochromator	θmax = 27.0°, θmin = 2.0°
ω scans	h = −1→25
Absorption correction: multi-scan (SADABS; Sheldrick 1996)	k = 0→12
Tmin = 0.862, Tmax = 0.887	l = 0→14
1561 measured reflections	3 standard reflections every 97 reflections
1317 independent reflections	intensity decay: 3.6%

Refinement

Refinement on F^2	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F^2 > 2σ(F^2)] = 0.031	H-atom parameters constrained
wR(F^2) = 0.070	w = 1/[σ^2(Fo^2) + (0.0399P)^2] where P = (Fo^2 + 2Fc^2)/3
S = 0.96	(Δ/σ)max < 0.001
1317 reflections	Δρmax = 0.15 e Å^−3
155 parameters	Δρmin = −0.13 e Å^−3
1 restraint	Extinction correction: SHELXL, Fc^*=kFc[1+0.001xFc^2λ^3/sin(2θ)]^-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.0017 (4)

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
S	0.40656 (3)	0.55154 (7)	0.40899 (6)	0.04033 (18)
N1	0.38746 (11)	0.5360 (2)	0.63259 (18)	0.0391 (5)
N2	0.47127 (10)	0.6876 (2)	0.57604 (18)	0.0427 (6)
H2N	0.4904	0.7294	0.5198	0.051*
N3	0.45966 (11)	0.8253 (2)	0.87048 (19)	0.0484 (6)
C1	0.34629 (12)	0.4379 (3)	0.4600 (2)	0.0360 (6)
C2	0.30604 (13)	0.3503 (3)	0.3974 (3)	0.0484 (7)
H2	0.3081	0.3476	0.3172	0.058*
C3	0.26279 (15)	0.2673 (3)	0.4574 (3)	0.0539 (8)
H3	0.2355	0.2072	0.4171	0.065*
C4	0.25943 (15)	0.2718 (4)	0.5759 (3)	0.0566 (9)
H4	0.2298	0.2153	0.6147	0.068*
C5	0.29973 (14)	0.3598 (3)	0.6381 (2)	0.0508 (7)
H5	0.2970	0.3625	0.7182	0.061*
C6	0.34423 (12)	0.4438 (3)	0.5805 (2)	0.0363 (6)
C7	0.42297 (12)	0.5963 (3)	0.5538 (2)	0.0340 (5)
C8	0.49156 (15)	0.7167 (3)	0.6939 (2)	0.0430 (6)
H8A	0.5366	0.7516	0.6926	0.052*
H8B	0.4920	0.6315	0.7369	0.052*
C9	0.44832 (13)	0.8177 (2)	0.7572 (2)	0.0381 (6)
C10	0.40108 (15)	0.8963 (3)	0.7032 (3)	0.0506 (7)
H10	0.3937	0.8868	0.6243	0.061*
C11	0.36489 (15)	0.9889 (4)	0.7661 (4)	0.0622 (9)
H11	0.3332	1.0436	0.7304	0.075*
C12	0.37597 (17)	0.9995 (4)	0.8820 (4)	0.0690 (10)
H12	0.3524	1.0615	0.9270	0.083*
C13	0.42350 (17)	0.9149 (3)	0.9303 (3)	0.0685 (10)
H13	0.4307	0.9210	1.0094	0.082*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
S	0.0422 (3)	0.0535 (4)	0.0252 (3)	−0.0052 (3)	0.0020 (3)	−0.0010 (3)
N1	0.0449 (11)	0.0465 (14)	0.0258 (11)	−0.0047 (10)	0.0013 (10)	0.0010 (10)
N2	0.0462 (13)	0.0524 (13)	0.0296 (11)	−0.0146 (11)	0.0005 (10)	0.0012 (11)
N3	0.0541 (14)	0.0514 (14)	0.0397 (12)	0.0100 (12)	−0.0109 (11)	−0.0081 (11)
C1	0.0333 (13)	0.0411 (14)	0.0337 (14)	0.0039 (12)	−0.0011 (11)	0.0004 (12)
C2	0.0486 (14)	0.0577 (16)	0.0391 (15)	−0.0039 (13)	−0.0037 (15)	−0.0081 (16)
C3	0.0469 (18)	0.0526 (18)	0.062 (2)	−0.0110 (15)	−0.0100 (15)	−0.0056 (16)
C4	0.0502 (18)	0.060 (2)	0.060 (2)	−0.0134 (15)	0.0044 (16)	0.0041 (17)
C5	0.0539 (17)	0.0586 (18)	0.0399 (14)	−0.0116 (15)	0.0053 (14)	0.0061 (15)
C6	0.0375 (13)	0.0375 (14)	0.0340 (14)	0.0026 (11)	−0.0002 (11)	0.0006 (12)
C7	0.0353 (12)	0.0411 (13)	0.0255 (12)	0.0015 (11)	0.0015 (10)	−0.0027 (11)
C8	0.0441 (16)	0.0483 (14)	0.0366 (13)	−0.0072 (14)	−0.0051 (13)	−0.0025 (12)
C9	0.0422 (14)	0.0321 (13)	0.0400 (14)	−0.0044 (11)	−0.0065 (13)	0.0014 (11)
C10	0.0616 (18)	0.0473 (15)	0.0430 (16)	0.0015 (15)	−0.0135 (15)	0.0054 (14)
C11	0.0643 (19)	0.0482 (17)	0.074 (2)	0.0156 (17)	−0.017 (2)	0.0033 (17)
C12	0.072 (2)	0.0612 (18)	0.074 (3)	0.022 (2)	−0.012 (2)	−0.0188 (19)
C13	0.082 (2)	0.075 (2)	0.048 (2)	0.0244 (18)	−0.0155 (17)	−0.0237 (18)

Geometric parameters (Å, º)

S—C1	1.749 (3)	C4—C5	1.385 (4)
S—C7	1.766 (2)	C4—H4	0.9300
N1—C7	1.301 (3)	C5—C6	1.387 (4)
N1—C6	1.391 (3)	C5—H5	0.9300
N2—C7	1.345 (3)	C8—C9	1.507 (4)
N2—C8	1.453 (4)	C8—H8A	0.9700
N2—H2N	0.8600	C8—H8B	0.9700
N3—C13	1.334 (4)	C9—C10	1.374 (4)
N3—C9	1.334 (3)	C10—C11	1.372 (5)
C1—C2	1.384 (4)	C10—H10	0.9300
C1—C6	1.397 (3)	C11—C12	1.365 (6)
C2—C3	1.379 (4)	C11—H11	0.9300
C2—H2	0.9300	C12—C13	1.383 (4)
C3—C4	1.376 (4)	C12—H12	0.9300
C3—H3	0.9300	C13—H13	0.9300
C1—S—C7	88.05 (12)	N1—C7—N2	124.4 (2)
C7—N1—C6	109.5 (2)	N1—C7—S	116.83 (19)
C7—N2—C8	120.9 (2)	N2—C7—S	118.81 (18)
C7—N2—H2N	119.6	N2—C8—C9	115.0 (2)
C8—N2—H2N	119.6	N2—C8—H8A	108.5
C13—N3—C9	117.0 (3)	C9—C8—H8A	108.5
C2—C1—C6	122.1 (3)	N2—C8—H8B	108.5
C2—C1—S	128.5 (2)	C9—C8—H8B	108.5
C6—C1—S	109.4 (2)	H8A—C8—H8B	107.5
C3—C2—C1	118.0 (3)	N3—C9—C10	122.4 (3)
C3—C2—H2	121.0	N3—C9—C8	114.6 (2)
C1—C2—H2	121.0	C10—C9—C8	123.0 (2)
C4—C3—C2	121.0 (3)	C11—C10—C9	119.6 (3)
C4—C3—H3	119.5	C11—C10—H10	120.2
C2—C3—H3	119.5	C9—C10—H10	120.2
C3—C4—C5	120.7 (3)	C12—C11—C10	119.1 (3)
C3—C4—H4	119.6	C12—C11—H11	120.5
C5—C4—H4	119.6	C10—C11—H11	120.5
C4—C5—C6	119.7 (3)	C11—C12—C13	117.8 (3)
C4—C5—H5	120.1	C11—C12—H12	121.1
C6—C5—H5	120.1	C13—C12—H12	121.1
C5—C6—N1	125.4 (2)	N3—C13—C12	124.1 (3)
C5—C6—C1	118.4 (3)	N3—C13—H13	118.0
N1—C6—C1	116.2 (2)	C12—C13—H13	118.0
C7—S—C1—C2	−178.8 (3)	C6—N1—C7—S	1.6 (3)
C7—S—C1—C6	−0.2 (2)	C8—N2—C7—N1	5.7 (4)
C6—C1—C2—C3	0.1 (4)	C8—N2—C7—S	−173.2 (2)
S—C1—C2—C3	178.6 (2)	C1—S—C7—N1	−0.8 (2)
C1—C2—C3—C4	0.4 (5)	C1—S—C7—N2	178.2 (2)
C2—C3—C4—C5	−0.3 (6)	C7—N2—C8—C9	−82.1 (3)
C3—C4—C5—C6	−0.3 (5)	C13—N3—C9—C10	−1.0 (4)
C4—C5—C6—N1	−179.8 (3)	C13—N3—C9—C8	178.9 (2)
C4—C5—C6—C1	0.8 (4)	N2—C8—C9—N3	168.4 (2)
C7—N1—C6—C5	178.9 (3)	N2—C8—C9—C10	−11.8 (4)
C7—N1—C6—C1	−1.7 (3)	N3—C9—C10—C11	1.6 (5)
C2—C1—C6—C5	−0.7 (4)	C8—C9—C10—C11	−178.2 (3)
S—C1—C6—C5	−179.4 (2)	C9—C10—C11—C12	−1.0 (5)
C2—C1—C6—N1	179.8 (2)	C10—C11—C12—C13	−0.2 (6)
S—C1—C6—N1	1.1 (3)	C9—N3—C13—C12	−0.3 (5)
C6—N1—C7—N2	−177.4 (2)	C11—C12—C13—N3	0.9 (6)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
N2—H2N···N3^i	0.86	2.21	3.069 (3)	177

Symmetry code: (i) −x+1, y, z−1/2.