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

The title compound, C₁₁H₁₀N₄OS was synthesized as a candidate plant activator. In the crystal structure, the benzene ring and the thia­diazole ring are nearly coplanar, making a dihedral angle of 1.6 (5)°. Mol­ecules are linked by inter­molecular N—H...O hydrogen bonds [H...O = 2.27 (2) Å].

Key indicators

• Single-crystal X-ray study
• T = 294 K
• Mean [sigma](C-C) = 0.003 Å
• R factor = 0.031
• wR factor = 0.078
• Data-to-parameter ratio = 15.2

checkCIF/PLATON results

No syntax errors found



Alert level C
PLAT125_ALERT_4_C No _symmetry_space_group_name_Hall Given .......          ?
PLAT710_ALERT_4_C Delete 1-2-3 or 2-3-4 Linear Torsion Angle ... #         30
            N3  -C8  -C11 -N4    156.00  5.00   1.555   1.555   1.555   1.555
PLAT710_ALERT_4_C Delete 1-2-3 or 2-3-4 Linear Torsion Angle ... #         31
            C10 -C8  -C11 -N4     38.00  5.00   1.555   1.555   1.555   1.555
PLAT710_ALERT_4_C Delete 1-2-3 or 2-3-4 Linear Torsion Angle ... #         32
            C9  -C8  -C11 -N4    -82.00  5.00   1.555   1.555   1.555   1.555

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           26.53
           From the CIF: _reflns_number_total               2436
           Count of symmetry unique reflns         1372
           Completeness (_total/calc)            177.55%
           TEST3: Check Friedels for noncentro structure
           Estimate of Friedel pairs measured      1064
           Fraction of Friedel pairs measured     0.776
           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

   0 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
   0 ALERT type 3 Indicator that the structure quality may be low
   5 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.

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

Crystal data

C11H10N4OS	Dx = 1.365 Mg m^−3
Mr = 246.29	Melting point: 528 K
Orthorhombic, Pna21	Mo Kα radiation, λ = 0.71073 Å
a = 8.996 (2) Å	Cell parameters from 3339 reflections
b = 21.630 (6) Å	θ = 3.4–26.3°
c = 6.1600 (16) Å	µ = 0.26 mm^−1
V = 1198.6 (5) Å^3	T = 294 K
Z = 4	Block, colorless
F(000) = 512	0.26 × 0.22 × 0.18 mm

Data collection

Bruker SMART CCD area-detector diffractometer	2436 independent reflections
Radiation source: fine-focus sealed tube	2120 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.022
φ and ω scans	θmax = 26.5°, θmin = 2.5°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −9→11
Tmin = 0.928, Tmax = 0.954	k = −27→26
6784 measured reflections	l = −7→7

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 atoms treated by a mixture of independent and constrained refinement
wR(F^2) = 0.078	w = 1/[σ^2(Fo^2) + (0.0421P)^2 + 0.0902P] where P = (Fo^2 + 2Fc^2)/3
S = 1.05	(Δ/σ)max = 0.001
2436 reflections	Δρmax = 0.12 e Å^−3
160 parameters	Δρmin = −0.18 e Å^−3
1 restraint	Absolute structure: Flack (1983), 1064 Friedel pairs
Primary atom site location: structure-invariant direct methods	Absolute structure parameter: 0.01 (8)

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
S1	0.83353 (6)	0.32192 (2)	0.82183 (10)	0.05584 (16)
O1	0.80211 (17)	0.19573 (6)	0.8524 (3)	0.0621 (4)
N1	0.8179 (2)	0.39725 (8)	0.7443 (4)	0.0692 (6)
N2	0.7393 (3)	0.40445 (8)	0.5739 (4)	0.0681 (6)
N3	0.69976 (17)	0.12681 (7)	0.6227 (2)	0.0395 (3)
H3	0.667 (2)	0.1174 (11)	0.502 (4)	0.055 (7)*
N4	0.6325 (3)	0.08967 (9)	1.1496 (3)	0.0725 (6)
C1	0.72705 (19)	0.29696 (8)	0.6087 (3)	0.0400 (4)
C2	0.6835 (2)	0.34925 (9)	0.4903 (3)	0.0504 (5)
C3	0.5919 (3)	0.34319 (9)	0.3122 (4)	0.0647 (6)
H3A	0.5624	0.3779	0.2339	0.078*
C4	0.5450 (3)	0.28540 (10)	0.2517 (4)	0.0644 (6)
H4	0.4820	0.2809	0.1330	0.077*
C5	0.5910 (2)	0.23310 (9)	0.3675 (3)	0.0509 (5)
H5	0.5591	0.1943	0.3223	0.061*
C6	0.68229 (19)	0.23741 (8)	0.5466 (3)	0.0388 (4)
C7	0.7336 (2)	0.18482 (8)	0.6849 (3)	0.0405 (4)
C8	0.7326 (2)	0.07240 (8)	0.7562 (3)	0.0407 (4)
C9	0.8999 (3)	0.05961 (12)	0.7691 (5)	0.0731 (7)
H9A	0.9370	0.0500	0.6269	0.110*
H9B	0.9174	0.0253	0.8644	0.110*
H9C	0.9500	0.0955	0.8241	0.110*
C10	0.6492 (2)	0.01713 (8)	0.6619 (4)	0.0525 (5)
H10A	0.5450	0.0265	0.6541	0.079*
H10B	0.6640	−0.0183	0.7533	0.079*
H10C	0.6860	0.0084	0.5189	0.079*
C11	0.6760 (2)	0.08367 (9)	0.9786 (3)	0.0483 (5)

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
S1	0.0616 (3)	0.0449 (3)	0.0610 (3)	−0.0134 (2)	−0.0064 (3)	−0.0064 (3)
O1	0.0896 (11)	0.0428 (7)	0.0540 (9)	−0.0110 (6)	−0.0338 (9)	0.0018 (8)
N1	0.0797 (13)	0.0409 (10)	0.0871 (16)	−0.0149 (9)	0.0001 (11)	−0.0044 (10)
N2	0.0830 (14)	0.0369 (9)	0.0845 (16)	−0.0069 (9)	0.0111 (13)	0.0016 (10)
N3	0.0586 (9)	0.0332 (8)	0.0268 (7)	−0.0023 (7)	−0.0059 (7)	0.0006 (6)
N4	0.1293 (19)	0.0535 (11)	0.0349 (10)	−0.0157 (11)	0.0019 (11)	−0.0007 (8)
C1	0.0404 (9)	0.0379 (9)	0.0416 (9)	−0.0039 (8)	0.0050 (8)	0.0024 (8)
C2	0.0603 (13)	0.0372 (10)	0.0536 (12)	0.0011 (9)	0.0106 (10)	0.0082 (8)
C3	0.0915 (15)	0.0479 (10)	0.0546 (13)	0.0126 (10)	−0.0049 (13)	0.0124 (11)
C4	0.0827 (16)	0.0657 (13)	0.0448 (11)	0.0082 (12)	−0.0166 (10)	0.0068 (10)
C5	0.0678 (13)	0.0444 (10)	0.0406 (11)	−0.0014 (9)	−0.0092 (9)	−0.0009 (8)
C6	0.0455 (10)	0.0358 (9)	0.0351 (9)	−0.0017 (7)	0.0004 (7)	0.0028 (7)
C7	0.0497 (10)	0.0367 (9)	0.0350 (9)	−0.0050 (7)	−0.0051 (8)	0.0020 (7)
C8	0.0545 (11)	0.0325 (8)	0.0350 (9)	0.0018 (8)	−0.0037 (8)	0.0013 (7)
C9	0.0626 (13)	0.0671 (13)	0.0895 (19)	0.0149 (11)	−0.0053 (13)	0.0076 (13)
C10	0.0818 (14)	0.0322 (9)	0.0436 (10)	−0.0007 (9)	−0.0078 (10)	−0.0012 (8)
C11	0.0753 (15)	0.0362 (10)	0.0333 (10)	−0.0057 (9)	−0.0113 (9)	0.0034 (7)

Geometric parameters (Å, º)

S1—N1	1.704 (2)	C4—C5	1.400 (3)
S1—C1	1.712 (2)	C4—H4	0.9300
O1—C7	1.225 (2)	C5—C6	1.378 (3)
N1—N2	1.275 (3)	C5—H5	0.9300
N2—C2	1.394 (3)	C6—C7	1.494 (3)
N3—C7	1.347 (2)	C8—C11	1.482 (3)
N3—C8	1.466 (2)	C8—C10	1.527 (3)
N3—H3	0.83 (2)	C8—C9	1.532 (3)
N4—C11	1.131 (3)	C9—H9A	0.9600
C1—C2	1.402 (3)	C9—H9B	0.9600
C1—C6	1.403 (2)	C9—H9C	0.9600
C2—C3	1.378 (3)	C10—H10A	0.9600
C3—C4	1.371 (3)	C10—H10B	0.9600
C3—H3A	0.9300	C10—H10C	0.9600
N1—S1—C1	92.31 (10)	C1—C6—C7	117.04 (16)
N2—N1—S1	113.18 (15)	O1—C7—N3	122.21 (18)
N1—N2—C2	113.52 (19)	O1—C7—C6	119.29 (17)
C7—N3—C8	122.87 (16)	N3—C7—C6	118.49 (17)
C7—N3—H3	124.5 (16)	N3—C8—C11	108.51 (15)
C8—N3—H3	112.3 (16)	N3—C8—C10	108.43 (15)
C2—C1—C6	121.24 (19)	C11—C8—C10	108.17 (17)
C2—C1—S1	107.51 (15)	N3—C8—C9	111.85 (16)
C6—C1—S1	131.24 (15)	C11—C8—C9	108.60 (18)
C3—C2—N2	126.2 (2)	C10—C8—C9	111.18 (17)
C3—C2—C1	120.31 (19)	C8—C9—H9A	109.5
N2—C2—C1	113.5 (2)	C8—C9—H9B	109.5
C4—C3—C2	119.14 (19)	H9A—C9—H9B	109.5
C4—C3—H3A	120.4	C8—C9—H9C	109.5
C2—C3—H3A	120.4	H9A—C9—H9C	109.5
C3—C4—C5	120.5 (2)	H9B—C9—H9C	109.5
C3—C4—H4	119.8	C8—C10—H10A	109.5
C5—C4—H4	119.8	C8—C10—H10B	109.5
C6—C5—C4	121.97 (18)	H10A—C10—H10B	109.5
C6—C5—H5	119.0	C8—C10—H10C	109.5
C4—C5—H5	119.0	H10A—C10—H10C	109.5
C5—C6—C1	116.84 (17)	H10B—C10—H10C	109.5
C5—C6—C7	126.08 (17)	N4—C11—C8	177.1 (2)
C1—S1—N1—N2	0.31 (18)	C2—C1—C6—C5	−1.5 (3)
S1—N1—N2—C2	0.3 (3)	S1—C1—C6—C5	177.89 (15)
N1—S1—C1—C2	−0.78 (15)	C2—C1—C6—C7	−179.48 (16)
N1—S1—C1—C6	179.76 (19)	S1—C1—C6—C7	−0.1 (3)
N1—N2—C2—C3	178.0 (2)	C8—N3—C7—O1	4.3 (3)
N1—N2—C2—C1	−0.9 (3)	C8—N3—C7—C6	−174.20 (16)
C6—C1—C2—C3	1.7 (3)	C5—C6—C7—O1	−172.53 (19)
S1—C1—C2—C3	−177.86 (16)	C1—C6—C7—O1	5.2 (3)
C6—C1—C2—N2	−179.39 (17)	C5—C6—C7—N3	6.0 (3)
S1—C1—C2—N2	1.1 (2)	C1—C6—C7—N3	−176.24 (16)
N2—C2—C3—C4	−179.2 (2)	C7—N3—C8—C11	50.1 (2)
C1—C2—C3—C4	−0.4 (3)	C7—N3—C8—C10	167.37 (17)
C2—C3—C4—C5	−0.9 (4)	C7—N3—C8—C9	−69.7 (2)
C3—C4—C5—C6	1.1 (4)	N3—C8—C11—N4	156 (5)
C4—C5—C6—C1	0.2 (3)	C10—C8—C11—N4	38 (5)
C4—C5—C6—C7	177.9 (2)	C9—C8—C11—N4	−82 (5)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
N3—H3···N4^i	0.83 (2)	2.27 (2)	3.083 (3)	166.8 (19)

Symmetry code: (i) x, y, z−1.