N-(1-Cyano-1-methyl­butyl)-1,2,3-benzothia­diazole-7-carboxamide

Ai, Y.-W.; Liu, F.-L.; Fan, Z.-J.; Song, H.-B.; Nie, K.-S.

doi:10.1107/S1600536805034379

N-(1-Cyano-1-methylbutyl)-1,2,3-benzothiadiazole-7-carboxamide

Y.-W. Ai, F.-L. Liu, Z.-J. Fan, H.-B. Song and K.-S. Nie

In the title compound, C₁₃H₁₄N₄OS, which was synthesized as a candidate plant activator by the reaction of 1-amino-1-methyl-1-propylacetonitrile and 1,2,3-benzothiadiazole-7-carbonyl chloride, the benzothiadiazole moiety is essentially planar, forming a dihedral angle of 14.5 (4)° with the amide group. In the crystal structure, molecules are linked by intermolecular N—H

O hydrogen bonds [H

O = 2.20 (4) Å] to form extended chains in the a-axis direction.

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Supporting information

	Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536805034379/lh6515sup1.cif Contains datablocks global, I
	Structure factor file (CIF format) https://doi.org/10.1107/S1600536805034379/lh6515Isup2.hkl Contains datablock I

CCDC reference: 289802

checkCIF report

Key indicators

Single-crystal X-ray study
T = 294 K
Mean (C-C) = 0.005 Å
R factor = 0.040
wR factor = 0.107
Data-to-parameter ratio = 14.2

checkCIF/PLATON results

No syntax errors found



Alert level C
PLAT222_ALERT_3_C Large Non-Solvent    H     Ueq(max)/Ueq(min) ...       3.53 Ratio
PLAT340_ALERT_3_C Low Bond Precision on C-C bonds (x 1000) Ang ...          5
PLAT705_ALERT_1_C D-H     Calc     0.86(2), Rep     0.89(4), Dev..       1.50 Sigma
              N3   -H3      1.555   1.555
PLAT706_ALERT_1_C H...A   Calc     2.23(2), Rep     2.20(4), Dev..       1.50 Sigma
              H3   -N4      1.555   1.655

Alert level G
REFLT03_ALERT_4_G Please check that the estimate of the number of Friedel pairs is
            correct. If it is not, please give the correct count in the
            _publ_section_exptl_refinement section of the submitted CIF.
           From the CIF: _diffrn_reflns_theta_max           26.41
           From the CIF: _reflns_number_total               2534
           Count of symmetry unique reflns         1437
           Completeness (_total/calc)            176.34%
           TEST3: Check Friedels for noncentro structure
           Estimate of Friedel pairs measured      1097
           Fraction of Friedel pairs measured     0.763
           Are heavy atom types Z>Si present        yes

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

   2 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
   0 ALERT type 2 Indicator that the structure model may be wrong or deficient
   2 ALERT type 3 Indicator that the structure quality may be low
   1 ALERT type 4 Improvement, methodology, query or suggestion

Computing details top

Data collection: SMART (Bruker, 1998); cell refinement: SAINT (Bruker, 1999); data reduction: SAINT; 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.

N-(1-Cyano-1-methylbutyl)-1,2,3-benzothiadiazole-7-carboxamide top

Crystal data top

C₁₃H₁₄N₄OS	F(000) = 288
M_r = 274.34	D_x = 1.359 Mg m⁻³
Monoclinic, P2₁	Melting point: 420 K
Hall symbol: P 2yb	Mo Kα radiation, λ = 0.71073 Å
a = 6.236 (2) Å	Cell parameters from 2025 reflections
b = 13.263 (4) Å	θ = 2.5–24.6°
c = 8.667 (3) Å	µ = 0.24 mm⁻¹
β = 110.740 (5)°	T = 294 K
V = 670.4 (4) Å³	Block, colourless
Z = 2	0.32 × 0.24 × 0.20 mm

Data collection top

Bruker SMART-CCD area-detector diffractometer	2534 independent reflections
Radiation source: fine-focus sealed tube	2262 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.022
φ and ω scans	θ_max = 26.4°, θ_min = 1.5°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −7→7
T_min = 0.920, T_max = 0.953	k = −13→16
3879 measured reflections	l = −7→10

Refinement top

Refinement on F²	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F² > 2σ(F²)] = 0.040	H atoms treated by a mixture of independent and constrained refinement
wR(F²) = 0.107	w = 1/[σ²(F_o²) + (0.0645P)²] where P = (F_o² + 2F_c²)/3
S = 1.07	(Δ/σ)_max < 0.001
2534 reflections	Δρ_max = 0.18 e Å⁻³
179 parameters	Δρ_min = −0.18 e Å⁻³
2 restraints	Absolute structure: Flack (1983), with 1097 Friedel pairs
Primary atom site location: structure-invariant direct methods	Absolute structure parameter: 0.03 (12)

Special details top

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 (Å²) top

	x	y	z	U_iso*/U_eq
S1	0.37006 (15)	0.56323 (6)	0.30495 (12)	0.0557 (3)
N1	0.5496 (7)	0.4671 (3)	0.3992 (5)	0.0686 (10)
N2	0.7566 (6)	0.4956 (2)	0.4724 (4)	0.0605 (9)
N3	0.3845 (4)	0.8910 (2)	0.1646 (3)	0.0406 (6)
H3	0.516 (3)	0.911 (2)	0.165 (4)	0.032 (8)*
N4	−0.1630 (5)	0.9611 (2)	0.1301 (4)	0.0503 (7)
O1	0.1902 (4)	0.75216 (19)	0.1889 (4)	0.0555 (7)
C1	0.5890 (5)	0.7524 (2)	0.3353 (4)	0.0363 (6)
C2	0.5865 (6)	0.6493 (2)	0.3652 (4)	0.0382 (7)
C3	0.7852 (6)	0.5976 (2)	0.4571 (4)	0.0421 (8)
C4	0.9930 (6)	0.6495 (3)	0.5258 (4)	0.0489 (8)
H4	1.1262	0.6156	0.5877	0.059*
C5	0.9958 (6)	0.7506 (3)	0.4998 (4)	0.0501 (8)
H5	1.1321	0.7863	0.5456	0.060*
C6	0.7958 (5)	0.8017 (2)	0.4050 (4)	0.0439 (8)
H6	0.8027	0.8707	0.3885	0.053*
C7	0.3703 (5)	0.7988 (2)	0.2244 (4)	0.0389 (7)
C8	0.1911 (5)	0.9400 (2)	0.0372 (4)	0.0370 (7)
C9	−0.0064 (5)	0.9485 (2)	0.0973 (4)	0.0379 (7)
C10	0.2630 (5)	1.0476 (3)	0.0096 (4)	0.0439 (8)
H10A	0.3960	1.0431	−0.0234	0.053*
H10B	0.1397	1.0776	−0.0813	0.053*
C11	0.3198 (7)	1.1172 (2)	0.1557 (5)	0.0525 (9)
H11A	0.4323	1.0852	0.2507	0.063*
H11B	0.1826	1.1291	0.1815	0.063*
C12	0.4134 (9)	1.2170 (3)	0.1235 (7)	0.0754 (14)
H12A	0.5497	1.2055	0.0987	0.113*
H12B	0.4493	1.2589	0.2197	0.113*
H12C	0.3006	1.2499	0.0317	0.113*
C13	0.1143 (6)	0.8803 (3)	−0.1240 (4)	0.0517 (9)
H13A	0.2337	0.8813	−0.1699	0.077*
H13B	−0.0220	0.9102	−0.2008	0.077*
H13C	0.0830	0.8119	−0.1027	0.077*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
S1	0.0518 (5)	0.0413 (4)	0.0667 (5)	−0.0104 (4)	0.0121 (4)	−0.0008 (4)
N1	0.086 (3)	0.0375 (16)	0.071 (2)	−0.0021 (18)	0.015 (2)	0.0004 (16)
N2	0.076 (3)	0.0363 (16)	0.060 (2)	0.0128 (15)	0.0127 (18)	0.0008 (14)
N3	0.0237 (13)	0.0432 (14)	0.0538 (15)	0.0033 (10)	0.0125 (11)	0.0106 (12)
N4	0.0291 (14)	0.0591 (17)	0.0643 (17)	0.0029 (13)	0.0184 (12)	0.0124 (14)
O1	0.0320 (12)	0.0476 (13)	0.0808 (18)	−0.0026 (10)	0.0125 (11)	0.0156 (12)
C1	0.0360 (16)	0.0358 (15)	0.0370 (16)	0.0029 (12)	0.0126 (13)	0.0043 (13)
C2	0.0378 (16)	0.0362 (16)	0.0383 (16)	−0.0016 (13)	0.0107 (13)	−0.0022 (13)
C3	0.050 (2)	0.0385 (16)	0.0344 (16)	0.0095 (13)	0.0106 (14)	0.0014 (12)
C4	0.0419 (18)	0.0516 (19)	0.0442 (17)	0.0148 (17)	0.0042 (15)	0.0067 (15)
C5	0.0346 (17)	0.060 (2)	0.0460 (18)	−0.0051 (16)	0.0022 (14)	0.0037 (15)
C6	0.0381 (18)	0.0406 (18)	0.0458 (18)	−0.0021 (14)	0.0060 (15)	0.0073 (14)
C7	0.0293 (16)	0.0412 (16)	0.0452 (17)	0.0020 (12)	0.0119 (13)	0.0059 (13)
C8	0.0278 (14)	0.0411 (16)	0.0406 (16)	0.0059 (12)	0.0103 (11)	0.0056 (13)
C9	0.0272 (15)	0.0398 (16)	0.0421 (16)	0.0019 (12)	0.0066 (12)	0.0046 (13)
C10	0.0326 (15)	0.050 (2)	0.0499 (16)	0.0094 (14)	0.0155 (13)	0.0155 (15)
C11	0.050 (2)	0.0412 (18)	0.064 (2)	−0.0094 (15)	0.0174 (18)	0.0043 (15)
C12	0.069 (3)	0.049 (2)	0.101 (4)	−0.016 (2)	0.022 (3)	0.009 (2)
C13	0.047 (2)	0.055 (2)	0.0493 (18)	0.0132 (16)	0.0128 (15)	0.0008 (16)

Geometric parameters (Å, º) top

S1—C2	1.702 (3)	C5—H5	0.9300
S1—N1	1.703 (4)	C6—H6	0.9300
N1—N2	1.278 (5)	C8—C9	1.501 (4)
N2—C3	1.377 (5)	C8—C13	1.528 (5)
N3—C7	1.344 (4)	C8—C10	1.540 (5)
N3—C8	1.467 (4)	C10—C11	1.505 (5)
N3—H3	0.862 (10)	C10—H10A	0.9700
N4—C9	1.122 (4)	C10—H10B	0.9700
O1—C7	1.222 (4)	C11—C12	1.512 (5)
C1—C6	1.380 (4)	C11—H11A	0.9700
C1—C2	1.393 (4)	C11—H11B	0.9700
C1—C7	1.494 (4)	C12—H12A	0.9600
C2—C3	1.393 (5)	C12—H12B	0.9600
C3—C4	1.401 (5)	C12—H12C	0.9600
C4—C5	1.361 (5)	C13—H13A	0.9600
C4—H4	0.9300	C13—H13B	0.9600
C5—C6	1.401 (5)	C13—H13C	0.9600

C2—S1—N1	92.29 (17)	C9—C8—C13	109.0 (3)
N2—N1—S1	113.2 (3)	N3—C8—C10	108.7 (2)
N1—N2—C3	112.7 (3)	C9—C8—C10	107.7 (3)
C7—N3—C8	123.0 (3)	C13—C8—C10	110.6 (3)
C7—N3—H3	119 (2)	N4—C9—C8	173.4 (3)
C8—N3—H3	113 (2)	C11—C10—C8	115.6 (2)
C6—C1—C2	117.0 (3)	C11—C10—H10A	108.4
C6—C1—C7	125.8 (3)	C8—C10—H10A	108.4
C2—C1—C7	117.1 (3)	C11—C10—H10B	108.4
C3—C2—C1	121.6 (3)	C8—C10—H10B	108.4
C3—C2—S1	107.1 (3)	H10A—C10—H10B	107.4
C1—C2—S1	131.4 (2)	C10—C11—C12	111.9 (3)
N2—C3—C2	114.8 (4)	C10—C11—H11A	109.2
N2—C3—C4	125.0 (3)	C12—C11—H11A	109.2
C2—C3—C4	120.2 (3)	C10—C11—H11B	109.2
C5—C4—C3	118.6 (3)	C12—C11—H11B	109.2
C5—C4—H4	120.7	H11A—C11—H11B	107.9
C3—C4—H4	120.7	C11—C12—H12A	109.5
C4—C5—C6	120.8 (3)	C11—C12—H12B	109.5
C4—C5—H5	119.6	H12A—C12—H12B	109.5
C6—C5—H5	119.6	C11—C12—H12C	109.5
C1—C6—C5	121.8 (3)	H12A—C12—H12C	109.5
C1—C6—H6	119.1	H12B—C12—H12C	109.5
C5—C6—H6	119.1	C8—C13—H13A	109.5
O1—C7—N3	122.9 (3)	C8—C13—H13B	109.5
O1—C7—C1	120.1 (3)	H13A—C13—H13B	109.5
N3—C7—C1	116.9 (3)	C8—C13—H13C	109.5
N3—C8—C9	109.2 (2)	H13A—C13—H13C	109.5
N3—C8—C13	111.5 (3)	H13B—C13—H13C	109.5

C2—S1—N1—N2	0.6 (3)	C2—C1—C6—C5	0.8 (5)
S1—N1—N2—C3	−0.2 (4)	C7—C1—C6—C5	−176.1 (3)
C6—C1—C2—C3	−1.9 (5)	C4—C5—C6—C1	0.4 (6)
C7—C1—C2—C3	175.4 (3)	C8—N3—C7—O1	−7.0 (5)
C6—C1—C2—S1	179.1 (3)	C8—N3—C7—C1	171.4 (3)
C7—C1—C2—S1	−3.6 (5)	C6—C1—C7—O1	−169.4 (3)
N1—S1—C2—C3	−0.8 (3)	C2—C1—C7—O1	13.6 (5)
N1—S1—C2—C1	178.4 (3)	C6—C1—C7—N3	12.2 (5)
N1—N2—C3—C2	−0.4 (5)	C2—C1—C7—N3	−164.8 (3)
N1—N2—C3—C4	179.5 (4)	C7—N3—C8—C9	58.1 (4)
C1—C2—C3—N2	−178.4 (3)	C7—N3—C8—C13	−62.5 (4)
S1—C2—C3—N2	0.8 (4)	C7—N3—C8—C10	175.3 (3)
C1—C2—C3—C4	1.6 (5)	N3—C8—C10—C11	−63.1 (4)
S1—C2—C3—C4	−179.1 (3)	C9—C8—C10—C11	55.1 (3)
N2—C3—C4—C5	179.7 (4)	C13—C8—C10—C11	174.1 (3)
C2—C3—C4—C5	−0.3 (5)	C8—C10—C11—C12	173.7 (3)
C3—C4—C5—C6	−0.7 (5)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N3—H3···N4ⁱ	0.89 (4)	2.20 (4)	3.083 (4)	173 (3)

Symmetry code: (i) x+1, y, z.

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N-(1-Cyano-1-methyl­butyl)-1,2,3-benzothia­diazole-7-carboxamide

Supporting information

Key indicators

checkCIF/PLATON results

N-(1-Cyano-1-methylbutyl)-1,2,3-benzothiadiazole-7-carboxamide