(1,3-Benzothia­zol-2-yl)[1-(2-chloro­benz­yl)imidazolidin-2-ylidene]amine

In the crystal structure of the title compound, C₁₇H₁₅ClN₄S, the benzothiazole, imidazolidine and benzene rings are twisted relative to each other.

Key indicators

• Single-crystal X-ray study
• T = 293 K
• Mean [sigma](C-C) = 0.002 Å
• R factor = 0.046
• wR factor = 0.135
• Data-to-parameter ratio = 33.7

checkCIF/PLATON results

No syntax errors found



Alert level C
PLAT063_ALERT_3_C Crystal Probably too Large for Beam Size .......       0.76 mm
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
PLAT200_ALERT_1_G Check the Reported _diffrn_ambient_temperature .        293 K

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

   2 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
   1 ALERT type 3 Indicator that the structure quality may be low
   0 ALERT type 4 Improvement, methodology, query or suggestion
   0 ALERT type 5 Informative message, check

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Computing details

Data collection: SMART (Siemens, 1996); cell refinement: SMART; data reduction: SAINT (Siemens, 1996); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEP-3 (Farrugia, 1997); software used to prepare material for publication: Win GX (Farrugia, 1999).

(1,3-Benzothiazol-2-yl)[1-(2-chlorobenzyl)imidazolidin-2-ylidene]amine

Crystal data

C17H15ClN4S	F(000) = 1424
Mr = 342.85	Dx = 1.431 Mg m^−3
Monoclinic, C2/c	Mo Kα radiation, λ = 0.71069 Å
Hall symbol: -C 2yc	Cell parameters from 6246 reflections
a = 20.0595 (3) Å	θ = 2.2–32.6°
b = 10.6269 (2) Å	µ = 0.38 mm^−1
c = 15.0647 (2) Å	T = 293 K
β = 97.572 (1)°	Block, colourless
V = 3183.34 (9) Å^3	0.76 × 0.45 × 0.44 mm
Z = 8

Data collection

Siemens SMART CCD area-detector diffractometer	4725 reflections with I > 2σ(I)
Radiation source: sealed tube	Rint = 0.025
Graphite monochromator	θmax = 35.1°, θmin = 2.1°
φ and ω scans	h = −32→31
34371 measured reflections	k = −17→16
7012 independent reflections	l = −24→23

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: inferred from neighbouring sites
wR(F^2) = 0.135	H-atom parameters constrained
S = 1.03	w = 1/[σ^2(Fo^2) + (0.0611P)^2 + 1.0812P] where P = (Fo^2 + 2Fc^2)/3
7012 reflections	(Δ/σ)max = 0.001
208 parameters	Δρmax = 0.35 e Å^−3
0 restraints	Δρmin = −0.31 e Å^−3

Special details

Geometry. Bond distances, angles etc. have been calculated using the rounded fractional coordinates. All su's are estimated from the variances of the (full) variance-covariance matrix. The cell e.s.d.'s are taken into account in the estimation of distances, angles and torsion angles

Refinement. Refinement on F² for ALL reflections except those flagged by the user for potential systematic errors. Weighted R-factors wR and all goodnesses of fit S are based on F², conventional R-factors R are based on F, with F set to zero for negative F². The observed criterion of F² > σ(F²) is used only for calculating -R-factor-obs 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
Cl1	0.21165 (2)	−0.24033 (4)	1.17837 (3)	0.0633 (1)
S1	0.09284 (2)	0.48759 (3)	1.02029 (2)	0.0498 (1)
N1	0.14262 (5)	0.38995 (10)	0.88465 (7)	0.0406 (3)
N2	0.14773 (6)	0.26105 (9)	1.01750 (7)	0.0412 (3)
N3	0.17997 (6)	0.14563 (11)	0.89233 (7)	0.0472 (3)
N4	0.19475 (6)	0.05992 (10)	1.02618 (7)	0.0446 (3)
C1	0.09229 (6)	0.57917 (12)	0.92472 (8)	0.0438 (3)
C2	0.06912 (8)	0.70176 (15)	0.90824 (10)	0.0573 (5)
C3	0.07460 (9)	0.75364 (14)	0.82526 (11)	0.0611 (5)
C4	0.10240 (8)	0.68605 (14)	0.76017 (10)	0.0560 (5)
C5	0.12566 (7)	0.56487 (13)	0.77680 (9)	0.0485 (4)
C6	0.12071 (6)	0.51007 (11)	0.85982 (8)	0.0387 (3)
C7	0.13211 (6)	0.36536 (11)	0.96722 (7)	0.0377 (3)
C8	0.17269 (5)	0.16317 (11)	0.97909 (7)	0.0368 (3)
C9	0.21557 (8)	0.02956 (14)	0.87953 (9)	0.0525 (4)
C10	0.21417 (7)	−0.03927 (12)	0.96822 (9)	0.0466 (4)
C11	0.18685 (7)	0.03865 (12)	1.11926 (8)	0.0431 (3)
C12	0.12727 (6)	−0.04472 (11)	1.12938 (7)	0.0388 (3)
C13	0.06237 (7)	0.00471 (14)	1.11059 (10)	0.0509 (4)
C14	0.00621 (7)	−0.06804 (17)	1.11621 (10)	0.0602 (5)
C15	0.01317 (8)	−0.19258 (17)	1.14181 (10)	0.0609 (5)
C16	0.07627 (9)	−0.24413 (14)	1.16185 (10)	0.0549 (5)
C17	0.13259 (7)	−0.17068 (12)	1.15488 (8)	0.0426 (3)
H2	0.05050	0.74730	0.95170	0.0690*
H3	0.16540	0.19670	0.84990	0.0570*
H3A	0.05940	0.83520	0.81280	0.0730*
H4	0.10540	0.72280	0.70480	0.0670*
H5	0.14440	0.52030	0.73310	0.0580*
H9A	0.26140	0.04620	0.86870	0.0630*
H9B	0.19280	−0.01860	0.82990	0.0630*
H10A	0.18150	−0.10700	0.96210	0.0560*
H10B	0.25800	−0.07320	0.99070	0.0560*
H11A	0.18110	0.11890	1.14790	0.0520*
H11B	0.22740	−0.00020	1.14950	0.0520*
H13	0.05700	0.08870	1.09390	0.0610*
H14	−0.03640	−0.03320	1.10270	0.0720*
H15	−0.02480	−0.24160	1.14550	0.0730*
H16	0.08120	−0.32770	1.17990	0.0660*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
Cl1	0.0673 (2)	0.0534 (2)	0.0698 (2)	0.0233 (2)	0.0115 (2)	0.0098 (2)
S1	0.0613 (2)	0.0501 (2)	0.0403 (2)	0.0162 (1)	0.0149 (1)	0.0020 (1)
N1	0.0470 (5)	0.0380 (5)	0.0380 (5)	0.0007 (4)	0.0104 (4)	0.0012 (4)
N2	0.0499 (5)	0.0386 (5)	0.0363 (5)	0.0038 (4)	0.0098 (4)	0.0015 (4)
N3	0.0602 (6)	0.0457 (6)	0.0368 (5)	0.0117 (5)	0.0111 (4)	0.0022 (4)
N4	0.0570 (6)	0.0397 (5)	0.0389 (5)	0.0077 (4)	0.0126 (4)	0.0037 (4)
C1	0.0451 (6)	0.0441 (6)	0.0419 (6)	0.0060 (5)	0.0047 (5)	0.0007 (5)
C2	0.0676 (9)	0.0478 (8)	0.0555 (8)	0.0164 (7)	0.0045 (6)	0.0005 (6)
C3	0.0710 (10)	0.0446 (8)	0.0647 (9)	0.0101 (7)	−0.0019 (7)	0.0087 (6)
C4	0.0651 (8)	0.0497 (8)	0.0522 (8)	−0.0026 (6)	0.0038 (6)	0.0136 (6)
C5	0.0549 (7)	0.0474 (7)	0.0444 (6)	−0.0019 (5)	0.0107 (5)	0.0053 (5)
C6	0.0379 (5)	0.0383 (6)	0.0397 (5)	−0.0024 (4)	0.0045 (4)	0.0008 (4)
C7	0.0387 (5)	0.0377 (5)	0.0371 (5)	−0.0004 (4)	0.0071 (4)	−0.0017 (4)
C8	0.0363 (5)	0.0383 (5)	0.0361 (5)	−0.0011 (4)	0.0060 (4)	0.0011 (4)
C9	0.0643 (8)	0.0507 (7)	0.0446 (6)	0.0137 (6)	0.0152 (6)	−0.0013 (5)
C10	0.0518 (7)	0.0412 (6)	0.0478 (6)	0.0067 (5)	0.0106 (5)	−0.0026 (5)
C11	0.0489 (6)	0.0433 (6)	0.0366 (5)	0.0007 (5)	0.0036 (4)	0.0035 (4)
C12	0.0456 (6)	0.0398 (6)	0.0310 (5)	0.0039 (4)	0.0053 (4)	0.0002 (4)
C13	0.0501 (7)	0.0498 (7)	0.0517 (7)	0.0090 (6)	0.0022 (5)	0.0012 (6)
C14	0.0456 (7)	0.0769 (11)	0.0570 (8)	0.0032 (7)	0.0030 (6)	−0.0063 (7)
C15	0.0570 (8)	0.0771 (11)	0.0500 (8)	−0.0199 (8)	0.0127 (6)	−0.0114 (7)
C16	0.0754 (10)	0.0449 (7)	0.0467 (7)	−0.0088 (6)	0.0164 (6)	−0.0014 (5)
C17	0.0531 (6)	0.0406 (6)	0.0348 (5)	0.0059 (5)	0.0089 (5)	0.0000 (4)

Geometric parameters (Å, º)

Cl1—C17	1.7436 (14)	C12—C17	1.3928 (17)
S1—C1	1.7367 (13)	C12—C13	1.3978 (19)
S1—C7	1.7644 (12)	C13—C14	1.378 (2)
N1—C6	1.3854 (16)	C14—C15	1.380 (3)
N1—C7	1.3150 (15)	C15—C16	1.376 (2)
N2—C7	1.3558 (15)	C16—C17	1.389 (2)
N2—C8	1.3205 (15)	C2—H2	0.9300
N3—C8	1.3471 (15)	C3—H3A	0.9300
N3—C9	1.4508 (19)	C4—H4	0.9300
N4—C8	1.3492 (16)	C5—H5	0.9300
N4—C10	1.4543 (17)	C9—H9A	0.9700
N4—C11	1.4495 (16)	C9—H9B	0.9700
N3—H3	0.8600	C10—H10A	0.9700
C1—C6	1.4025 (17)	C10—H10B	0.9700
C1—C2	1.394 (2)	C11—H11A	0.9700
C2—C3	1.384 (2)	C11—H11B	0.9700
C3—C4	1.390 (2)	C13—H13	0.9300
C4—C5	1.381 (2)	C14—H14	0.9300
C5—C6	1.3950 (18)	C15—H15	0.9300
C9—C10	1.5267 (19)	C16—H16	0.9300
C11—C12	1.5115 (18)
Cl1···C9^i	3.5602 (16)	C7···H3	2.6600
Cl1···H11B	2.6100	C12···H10A	2.9500
Cl1···H3^ii	2.9000	C14···H3A^iv	3.0600
S1···N1	2.6052 (11)	C17···H3^ii	2.9400
S1···C16^iii	3.6018 (15)	H3···N1	2.1800
S1···S1^iv	3.7035 (5)	H3···C7	2.6600
S1···H16^iii	3.1400	H3···Cl1^x	2.9000
S1···H9A^v	3.1900	H3···C17^x	2.9400
S1···H10B^v	3.1500	H3A···C14^iv	3.0600
N1···S1	2.6052 (11)	H3A···H14^iv	2.5300
N1···N3	2.7006 (16)	H4···H11A^xi	2.4900
N3···N1	2.7006 (16)	H5···H16^x	2.4800
N1···H3	2.1800	H9A···S1^v	3.1900
N1···H15^vi	2.8300	H10A···C2^ix	3.0600
N2···H11A	2.5000	H10A···C12	2.9500
N2···H13	2.9200	H10B···S1^v	3.1500
C3···C3^vii	3.509 (2)	H11A···N2	2.5000
C8···C13	3.5795 (18)	H11A···H13	2.5400
C8···C8^v	3.5927 (15)	H11A···H4^xii	2.4900
C9···Cl1^i	3.5602 (16)	H11B···Cl1	2.6100
C13···C8	3.5795 (18)	H11B···C5^v	3.0900
C13···C14^vi	3.575 (2)	H11B···C6^v	3.0700
C14···C13^vi	3.575 (2)	H13···N2	2.9200
C15···C15^viii	3.370 (2)	H13···H11A	2.5400
C16···S1^ix	3.6018 (15)	H14···H3A^iv	2.5300
C2···H10A^iii	3.0600	H15···N1^vi	2.8300
C5···H16^x	2.9900	H15···C7^vi	2.8800
C5···H11B^v	3.0900	H16···S1^ix	3.1400
C6···H11B^v	3.0700	H16···C5^ii	2.9900
C7···H15^vi	2.8800	H16···H5^ii	2.4800
C1—S1—C7	89.50 (6)	C12—C17—C16	121.84 (13)
C6—N1—C7	110.72 (10)	Cl1—C17—C12	119.90 (10)
C7—N2—C8	118.18 (10)	Cl1—C17—C16	118.25 (11)
C8—N3—C9	111.39 (10)	C1—C2—H2	121.00
C8—N4—C10	111.66 (10)	C3—C2—H2	121.00
C8—N4—C11	124.43 (11)	C2—C3—H3A	119.00
C10—N4—C11	122.68 (10)	C4—C3—H3A	119.00
C9—N3—H3	124.00	C3—C4—H4	120.00
C8—N3—H3	124.00	C5—C4—H4	120.00
C2—C1—C6	121.44 (12)	C4—C5—H5	120.00
S1—C1—C6	109.01 (9)	C6—C5—H5	120.00
S1—C1—C2	129.55 (10)	N3—C9—H9A	111.00
C1—C2—C3	117.95 (14)	N3—C9—H9B	111.00
C2—C3—C4	121.22 (14)	C10—C9—H9A	111.00
C3—C4—C5	120.74 (14)	C10—C9—H9B	111.00
C4—C5—C6	119.31 (13)	H9A—C9—H9B	109.00
C1—C6—C5	119.34 (11)	N4—C10—H10A	111.00
N1—C6—C1	115.97 (11)	N4—C10—H10B	111.00
N1—C6—C5	124.70 (11)	C9—C10—H10A	111.00
S1—C7—N1	114.78 (9)	C9—C10—H10B	111.00
S1—C7—N2	115.65 (8)	H10A—C10—H10B	109.00
N1—C7—N2	129.56 (11)	N4—C11—H11A	109.00
N2—C8—N3	129.05 (11)	N4—C11—H11B	109.00
N3—C8—N4	109.13 (10)	C12—C11—H11A	109.00
N2—C8—N4	121.82 (10)	C12—C11—H11B	109.00
N3—C9—C10	103.00 (11)	H11A—C11—H11B	108.00
N4—C10—C9	102.44 (10)	C12—C13—H13	119.00
N4—C11—C12	112.19 (10)	C14—C13—H13	119.00
C13—C12—C17	116.90 (12)	C13—C14—H14	120.00
C11—C12—C13	119.15 (11)	C15—C14—H14	120.00
C11—C12—C17	123.94 (11)	C14—C15—H15	120.00
C12—C13—C14	121.59 (14)	C16—C15—H15	120.00
C13—C14—C15	120.11 (14)	C15—C16—H16	120.00
C14—C15—C16	119.96 (15)	C17—C16—H16	120.00
C15—C16—C17	119.59 (14)
C7—S1—C1—C2	−178.77 (14)	S1—C1—C2—C3	−179.98 (12)
C7—S1—C1—C6	0.91 (9)	S1—C1—C6—N1	−0.51 (14)
C1—S1—C7—N2	177.99 (10)	C2—C1—C6—C5	−0.29 (19)
C1—S1—C7—N1	−1.23 (10)	C6—C1—C2—C3	0.4 (2)
C6—N1—C7—N2	−177.95 (12)	C2—C1—C6—N1	179.20 (12)
C7—N1—C6—C5	179.07 (12)	C1—C2—C3—C4	−0.1 (2)
C7—N1—C6—C1	−0.39 (15)	C2—C3—C4—C5	−0.3 (3)
C6—N1—C7—S1	1.13 (13)	C3—C4—C5—C6	0.3 (2)
C8—N2—C7—S1	175.14 (9)	C4—C5—C6—N1	−179.51 (13)
C8—N2—C7—N1	−5.8 (2)	C4—C5—C6—C1	−0.07 (19)
C7—N2—C8—N3	−6.73 (19)	N3—C9—C10—N4	−14.79 (14)
C7—N2—C8—N4	174.34 (11)	N4—C11—C12—C13	−74.15 (15)
C9—N3—C8—N2	174.53 (12)	N4—C11—C12—C17	104.45 (13)
C9—N3—C8—N4	−6.44 (15)	C11—C12—C13—C14	178.12 (13)
C8—N3—C9—C10	13.63 (15)	C17—C12—C13—C14	−0.6 (2)
C11—N4—C8—N2	7.26 (19)	C11—C12—C17—Cl1	0.68 (16)
C10—N4—C8—N3	−4.33 (14)	C11—C12—C17—C16	−178.92 (12)
C8—N4—C11—C12	98.08 (14)	C13—C12—C17—Cl1	179.31 (10)
C10—N4—C11—C12	−68.13 (16)	C13—C12—C17—C16	−0.29 (18)
C10—N4—C8—N2	174.79 (11)	C12—C13—C14—C15	0.7 (2)
C11—N4—C8—N3	−171.86 (12)	C13—C14—C15—C16	0.1 (2)
C11—N4—C10—C9	−179.90 (12)	C14—C15—C16—C17	−0.9 (2)
C8—N4—C10—C9	12.31 (14)	C15—C16—C17—Cl1	−178.56 (11)
S1—C1—C6—C5	180.00 (9)	C15—C16—C17—C12	1.1 (2)

Symmetry codes: (i) −x+1/2, −y−1/2, −z+2; (ii) x, −y, z+1/2; (iii) x, y+1, z; (iv) −x, −y+1, −z+2; (v) −x+1/2, −y+1/2, −z+2; (vi) −x, −y, −z+2; (vii) −x, y, −z+3/2; (viii) −x, y, −z+5/2; (ix) x, y−1, z; (x) x, −y, z−1/2; (xi) x, −y+1, z−1/2; (xii) x, −y+1, z+1/2.