Ethyl 1-(1,2,3-benzothia­diazol-7-ylcarbon­yl)piperidine-4-carboxyl­ate

The title compound, C₁₅H₁₇N₃O₃S, a potent new plant elicitor, was synthesized by reaction between 1,2,3-benzothia­diazole-7-carbonyl chloride and ethyl piperidine-4-carboxyl­ate. The piperidine ring adopts a chair conformation. Weak inter­molecular C—H...O hydrogen bonds stabilize the crystal packing.

Key indicators

• Single-crystal X-ray study
• T = 294 K
• Mean [sigma](C-C) = 0.004 Å
• Disorder in main residue
• R factor = 0.048
• wR factor = 0.162
• Data-to-parameter ratio = 13.9

checkCIF/PLATON results

No syntax errors found



Alert level C
PLAT125_ALERT_4_C No _symmetry_space_group_name_Hall Given .......          ?
PLAT220_ALERT_2_C Large Non-Solvent    C     Ueq(max)/Ueq(min) ...       2.53 Ratio
PLAT301_ALERT_3_C Main Residue  Disorder .........................      12.00 Perc.

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

   0 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
   1 ALERT type 4 Improvement, methodology, query or suggestion

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Computing details

Data collection: SMART (Bruker, 1998); cell refinement: SMART; data reduction: SAINT (Bruker, 1999); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: SHELXTL (Bruker, 1999); software used to prepare material for publication: SHELXTL.

Ethyl 1-(1,2,3-benzothiadiazole-7-carbonyl)piperidine-4-carboxylate

Crystal data

C15H17N3O3S	F(000) = 672
Mr = 319.38	Dx = 1.378 Mg m^−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
a = 15.465 (3) Å	Cell parameters from 2419 reflections
b = 12.284 (2) Å	θ = 2.7–23.7°
c = 8.1513 (15) Å	µ = 0.23 mm^−1
β = 96.094 (3)°	T = 294 K
V = 1539.8 (5) Å^3	Prism, colourless
Z = 4	0.32 × 0.28 × 0.20 mm

Data collection

Bruker SMART CCD area-detector diffractometer	3160 independent reflections
Radiation source: fine-focus sealed tube	1849 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.032
φ and ω scans	θmax = 26.5°, θmin = 1.3°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −19→19
Tmin = 0.92, Tmax = 0.951	k = −15→14
8514 measured reflections	l = −10→6

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)] = 0.048	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.162	H-atom parameters constrained
S = 0.98	w = 1/[σ^2(Fo^2) + (0.0854P)^2 + 0.2872P] where P = (Fo^2 + 2Fc^2)/3
3160 reflections	(Δ/σ)max = 0.001
227 parameters	Δρmax = 0.29 e Å^−3
66 restraints	Δρmin = −0.25 e Å^−3

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	Occ. (<1)
S1	0.34690 (6)	0.31165 (6)	1.14772 (10)	0.0747 (3)
O1	0.20134 (14)	0.3806 (2)	0.9103 (3)	0.0995 (8)
O2	0.18947 (17)	0.70608 (18)	0.1930 (3)	0.0982 (8)
N1	0.43103 (19)	0.3236 (2)	1.2999 (3)	0.0837 (8)
N2	0.46770 (16)	0.4168 (2)	1.3049 (3)	0.0741 (7)
N3	0.23696 (13)	0.46189 (18)	0.6791 (3)	0.0620 (6)
C1	0.36299 (16)	0.44036 (19)	1.0804 (3)	0.0545 (6)
C2	0.43042 (16)	0.4861 (2)	1.1825 (3)	0.0580 (6)
C3	0.45547 (17)	0.5941 (2)	1.1624 (4)	0.0664 (7)
H3A	0.5009	0.6248	1.2310	0.080*
C4	0.41114 (18)	0.6529 (2)	1.0387 (4)	0.0685 (8)
H4A	0.4255	0.7256	1.0254	0.082*
C5	0.34484 (17)	0.6064 (2)	0.9318 (4)	0.0645 (7)
H5A	0.3165	0.6488	0.8482	0.077*
C6	0.32010 (15)	0.49870 (19)	0.9469 (3)	0.0549 (6)
C7	0.24855 (17)	0.4424 (2)	0.8424 (4)	0.0645 (7)
C8	0.30513 (17)	0.4981 (2)	0.5788 (4)	0.0651 (7)
H8A	0.3265	0.4363	0.5211	0.078*
H8B	0.3534	0.5284	0.6501	0.078*
C9	0.27022 (17)	0.5827 (2)	0.4557 (3)	0.0621 (7)
H9A	0.3152	0.6031	0.3872	0.075*
H9B	0.2538	0.6472	0.5135	0.075*
C10	0.19175 (18)	0.5394 (2)	0.3473 (3)	0.0633 (7)
H10A	0.2111	0.4757	0.2889	0.076*
C11	0.12339 (18)	0.5003 (2)	0.4552 (4)	0.0687 (7)
H11A	0.1016	0.5620	0.5128	0.082*
H11B	0.0750	0.4685	0.3861	0.082*
C12	0.16059 (18)	0.4169 (2)	0.5797 (4)	0.0724 (8)
H12A	0.1169	0.3966	0.6511	0.087*
H12B	0.1771	0.3520	0.5228	0.087*
C13	0.1574 (2)	0.6208 (3)	0.2184 (4)	0.0836 (9)
O3	0.1047 (4)	0.5667 (5)	0.1035 (6)	0.0876 (18)	0.552 (9)
C14	0.0770 (5)	0.6261 (7)	−0.0468 (10)	0.100 (3)	0.552 (9)
H14A	0.0686	0.5753	−0.1382	0.121*	0.552 (9)
H14B	0.1223	0.6769	−0.0694	0.121*	0.552 (9)
C15	−0.0052 (5)	0.6869 (7)	−0.0347 (13)	0.099 (3)	0.552 (9)
H15A	−0.0217	0.7243	−0.1366	0.149*	0.552 (9)
H15B	0.0033	0.7389	0.0535	0.149*	0.552 (9)
H15C	−0.0503	0.6368	−0.0131	0.149*	0.552 (9)
O3'	0.0662 (4)	0.6076 (6)	0.1711 (10)	0.087 (2)	0.448 (9)
C14'	0.0200 (8)	0.6824 (9)	0.0499 (11)	0.114 (4)	0.448 (9)
H14C	0.0416	0.7561	0.0675	0.137*	0.448 (9)
H14D	−0.0418	0.6819	0.0606	0.137*	0.448 (9)
C15'	0.0367 (11)	0.6431 (12)	−0.1166 (13)	0.138 (5)	0.448 (9)
H15D	0.0058	0.6881	−0.1995	0.206*	0.448 (9)
H15E	0.0172	0.5691	−0.1308	0.206*	0.448 (9)
H15F	0.0979	0.6466	−0.1270	0.206*	0.448 (9)

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
S1	0.0980 (6)	0.0489 (4)	0.0791 (5)	0.0034 (3)	0.0179 (4)	0.0052 (4)
O1	0.0889 (15)	0.1151 (18)	0.0914 (15)	−0.0496 (14)	−0.0048 (12)	0.0342 (14)
O2	0.1287 (19)	0.0723 (14)	0.0949 (17)	−0.0197 (13)	0.0182 (15)	0.0200 (12)
N1	0.099 (2)	0.0791 (18)	0.0730 (17)	0.0250 (15)	0.0098 (15)	0.0067 (14)
N2	0.0728 (15)	0.0790 (17)	0.0708 (15)	0.0181 (13)	0.0096 (12)	−0.0002 (14)
N3	0.0520 (12)	0.0635 (13)	0.0707 (15)	−0.0131 (10)	0.0072 (11)	0.0045 (11)
C1	0.0547 (14)	0.0461 (13)	0.0652 (15)	0.0063 (11)	0.0187 (13)	−0.0019 (12)
C2	0.0522 (14)	0.0622 (16)	0.0610 (15)	0.0124 (12)	0.0116 (13)	−0.0057 (13)
C3	0.0538 (15)	0.0666 (17)	0.0790 (19)	−0.0003 (13)	0.0076 (14)	−0.0142 (15)
C4	0.0657 (17)	0.0460 (14)	0.095 (2)	−0.0055 (13)	0.0125 (16)	−0.0038 (15)
C5	0.0592 (15)	0.0531 (15)	0.0813 (19)	0.0036 (13)	0.0079 (14)	0.0063 (14)
C6	0.0478 (13)	0.0502 (14)	0.0673 (16)	0.0026 (11)	0.0094 (12)	0.0016 (12)
C7	0.0578 (16)	0.0584 (16)	0.0774 (19)	−0.0065 (12)	0.0074 (14)	0.0099 (14)
C8	0.0544 (15)	0.0639 (16)	0.0790 (18)	−0.0036 (12)	0.0164 (14)	−0.0062 (14)
C9	0.0641 (16)	0.0559 (15)	0.0702 (17)	−0.0079 (12)	0.0248 (14)	−0.0066 (13)
C10	0.0750 (17)	0.0513 (14)	0.0657 (16)	−0.0038 (13)	0.0173 (14)	−0.0039 (13)
C11	0.0598 (16)	0.0746 (18)	0.0710 (17)	−0.0095 (14)	0.0041 (14)	0.0064 (15)
C12	0.0660 (17)	0.0720 (18)	0.0780 (19)	−0.0206 (14)	0.0016 (15)	0.0103 (16)
C13	0.110 (3)	0.070 (2)	0.072 (2)	−0.0160 (19)	0.0121 (19)	0.0076 (17)
O3	0.105 (4)	0.082 (3)	0.073 (3)	−0.001 (3)	−0.004 (3)	0.008 (3)
C14	0.097 (5)	0.115 (5)	0.088 (5)	0.005 (4)	0.000 (4)	0.021 (4)
C15	0.092 (5)	0.104 (5)	0.102 (6)	0.013 (4)	0.015 (5)	0.020 (5)
O3'	0.102 (5)	0.077 (4)	0.076 (4)	−0.004 (3)	−0.015 (3)	0.011 (3)
C14'	0.118 (7)	0.118 (7)	0.100 (6)	0.004 (6)	−0.016 (6)	0.010 (6)
C15'	0.164 (9)	0.127 (8)	0.119 (7)	−0.008 (7)	0.000 (7)	0.009 (7)

Geometric parameters (Å, º)

S1—C1	1.700 (2)	C10—C13	1.506 (4)
S1—N1	1.706 (3)	C10—C11	1.523 (4)
O1—C7	1.226 (3)	C10—H10A	0.9800
O2—C13	1.186 (3)	C11—C12	1.513 (4)
N1—N2	1.276 (3)	C11—H11A	0.9700
N2—C2	1.389 (3)	C11—H11B	0.9700
N3—C7	1.345 (4)	C12—H12A	0.9700
N3—C12	1.468 (3)	C12—H12B	0.9700
N3—C8	1.470 (3)	C13—O3	1.349 (5)
C1—C2	1.383 (4)	C13—O3'	1.432 (6)
C1—C6	1.409 (3)	O3—C14	1.451 (7)
C2—C3	1.396 (4)	C14—C15	1.487 (8)
C3—C4	1.364 (4)	C14—H14A	0.9700
C3—H3A	0.9300	C14—H14B	0.9700
C4—C5	1.396 (4)	C15—H15A	0.9600
C4—H4A	0.9300	C15—H15B	0.9600
C5—C6	1.386 (3)	C15—H15C	0.9600
C5—H5A	0.9300	O3'—C14'	1.476 (8)
C6—C7	1.493 (4)	C14'—C15'	1.489 (9)
C8—C9	1.504 (4)	C14'—H14C	0.9700
C8—H8A	0.9700	C14'—H14D	0.9700
C8—H8B	0.9700	C15'—H15D	0.9600
C9—C10	1.519 (4)	C15'—H15E	0.9600
C9—H9A	0.9700	C15'—H15F	0.9600
C9—H9B	0.9700
C1—S1—N1	91.61 (14)	C11—C10—H10A	107.2
N2—N1—S1	113.7 (2)	C12—C11—C10	111.3 (2)
N1—N2—C2	112.2 (3)	C12—C11—H11A	109.4
C7—N3—C12	119.6 (2)	C10—C11—H11A	109.4
C7—N3—C8	125.2 (2)	C12—C11—H11B	109.4
C12—N3—C8	112.9 (2)	C10—C11—H11B	109.4
C2—C1—C6	121.4 (2)	H11A—C11—H11B	108.0
C2—C1—S1	108.1 (2)	N3—C12—C11	110.0 (2)
C6—C1—S1	130.5 (2)	N3—C12—H12A	109.7
C1—C2—N2	114.4 (2)	C11—C12—H12A	109.7
C1—C2—C3	121.1 (2)	N3—C12—H12B	109.7
N2—C2—C3	124.6 (3)	C11—C12—H12B	109.7
C4—C3—C2	117.8 (3)	H12A—C12—H12B	108.2
C4—C3—H3A	121.1	O2—C13—O3	123.1 (3)
C2—C3—H3A	121.1	O2—C13—O3'	118.1 (4)
C3—C4—C5	121.6 (2)	O2—C13—C10	125.8 (3)
C3—C4—H4A	119.2	O3—C13—C10	107.5 (3)
C5—C4—H4A	119.2	O3'—C13—C10	112.2 (3)
C6—C5—C4	121.7 (3)	C13—O3—C14	116.2 (5)
C6—C5—H5A	119.1	O3—C14—C15	112.0 (8)
C4—C5—H5A	119.1	O3—C14—H14A	109.2
C5—C6—C1	116.3 (2)	C15—C14—H14A	109.2
C5—C6—C7	125.9 (2)	O3—C14—H14B	109.2
C1—C6—C7	117.7 (2)	C15—C14—H14B	109.2
O1—C7—N3	122.3 (3)	H14A—C14—H14B	107.9
O1—C7—C6	118.0 (3)	C14—C15—H15A	109.5
N3—C7—C6	119.7 (2)	C14—C15—H15B	109.5
N3—C8—C9	110.6 (2)	H15A—C15—H15B	109.5
N3—C8—H8A	109.5	C14—C15—H15C	109.5
C9—C8—H8A	109.5	H15A—C15—H15C	109.5
N3—C8—H8B	109.5	H15B—C15—H15C	109.5
C9—C8—H8B	109.5	C13—O3'—C14'	120.2 (7)
H8A—C8—H8B	108.1	O3'—C14'—C15'	106.9 (11)
C8—C9—C10	110.8 (2)	O3'—C14'—H14C	110.3
C8—C9—H9A	109.5	C15'—C14'—H14C	110.3
C10—C9—H9A	109.5	O3'—C14'—H14D	110.3
C8—C9—H9B	109.5	C15'—C14'—H14D	110.3
C10—C9—H9B	109.5	H14C—C14'—H14D	108.6
H9A—C9—H9B	108.1	C14'—C15'—H15D	109.5
C13—C10—C9	112.0 (2)	C14'—C15'—H15E	109.5
C13—C10—C11	113.4 (2)	H15D—C15'—H15E	109.5
C9—C10—C11	109.6 (2)	C14'—C15'—H15F	109.5
C13—C10—H10A	107.2	H15D—C15'—H15F	109.5
C9—C10—H10A	107.2	H15E—C15'—H15F	109.5
C1—S1—N1—N2	1.6 (2)	C5—C6—C7—N3	40.1 (4)
S1—N1—N2—C2	−0.7 (3)	C1—C6—C7—N3	−144.6 (2)
N1—S1—C1—C2	−1.89 (19)	C7—N3—C8—C9	−139.4 (3)
N1—S1—C1—C6	178.0 (2)	C12—N3—C8—C9	58.0 (3)
C6—C1—C2—N2	−178.0 (2)	N3—C8—C9—C10	−56.5 (3)
S1—C1—C2—N2	1.9 (3)	C8—C9—C10—C13	−177.8 (2)
C6—C1—C2—C3	3.5 (4)	C8—C9—C10—C11	55.4 (3)
S1—C1—C2—C3	−176.7 (2)	C13—C10—C11—C12	178.6 (2)
N1—N2—C2—C1	−0.8 (3)	C9—C10—C11—C12	−55.4 (3)
N1—N2—C2—C3	177.7 (2)	C7—N3—C12—C11	139.0 (3)
C1—C2—C3—C4	0.1 (4)	C8—N3—C12—C11	−57.3 (3)
N2—C2—C3—C4	−178.4 (2)	C10—C11—C12—N3	55.9 (3)
C2—C3—C4—C5	−2.1 (4)	C9—C10—C13—O2	5.0 (5)
C3—C4—C5—C6	0.7 (4)	C11—C10—C13—O2	129.7 (4)
C4—C5—C6—C1	2.7 (4)	C9—C10—C13—O3	163.9 (4)
C4—C5—C6—C7	178.1 (2)	C11—C10—C13—O3	−71.4 (5)
C2—C1—C6—C5	−4.7 (3)	C9—C10—C13—O3'	−152.0 (5)
S1—C1—C6—C5	175.5 (2)	C11—C10—C13—O3'	−27.3 (6)
C2—C1—C6—C7	179.5 (2)	O2—C13—O3—C14	−9.8 (9)
S1—C1—C6—C7	−0.4 (3)	O3'—C13—O3—C14	86.7 (8)
C12—N3—C7—O1	6.2 (4)	C10—C13—O3—C14	−169.4 (6)
C8—N3—C7—O1	−155.3 (3)	C13—O3—C14—C15	−90.0 (8)
C12—N3—C7—C6	−172.8 (2)	O2—C13—O3'—C14'	19.0 (11)
C8—N3—C7—C6	25.7 (4)	O3—C13—O3'—C14'	−90.4 (9)
C5—C6—C7—O1	−138.9 (3)	C10—C13—O3'—C14'	177.9 (7)
C1—C6—C7—O1	36.4 (4)	C13—O3'—C14'—C15'	81.3 (12)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
C9—H9B···O2^i	0.97	2.59	3.542 (3)	169
C15—H15C···O1^ii	0.96	2.57	3.401 (8)	145

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