Methyl 2-[2-(tert-but-oxy-carbonyl-amino)-1,3-benzothia-zole-6-carboxamido]-acetate.

In the title compound, C(16)H(19)N(3)O(5)S, the dihedral angle between the benzene ring and the carbonyl-amino group is 18.18 (2)°. In the crystal, mol-ecules form centrosymmetric dimers via pairs of N-H⋯N hydrogen bonds. The dimers are connected via N-H⋯O hydrogen bonds into a three-dimensional network..

Related literature

For benzothia­zole derivatives with anti-tumor activity, see: Brantley et al. (2004 ▶); Ćaleta et al. (2009 ▶); Mortimer et al. (2006 ▶) and for benzothia­zolines with anti-tuberculous properties, see: Palmer et al. (1971 ▶). For related benzothia­zole structures, see: Lynch et al. (2002 ▶); Matković-Čalogović et al. (2003 ▶); Lei et al. (2010 ▶).

Experimental

Crystal data

C16H19N3O5S

M = 365.41

Monoclinic,

a = 16.861 (3) Å

b = 11.317 (2) Å

c = 9.6484 (19) Å

β = 98.94 (3)°

V = 1818.7 (6) Å3

Z = 4

Mo Kα radiation

μ = 0.21 mm−1

T = 293 K

0.54 × 0.33 × 0.12 mm

Data collection

Rigaku Saturn 724 CCD area-detector diffractometer

Absorption correction: numerical (NUMABS; Higashi, 2000 ▶) T min = 0.921, T max = 0.975

14817 measured reflections

4176 independent reflections

3718 reflections with I > 2σ(I)

R int = 0.054

Refinement

R[F 2 > 2σ(F 2)] = 0.083

wR(F 2) = 0.180

S = 1.26

4176 reflections

230 parameters

H-atom parameters constrained

Δρmax = 0.34 e Å−3

Δρmin = −0.23 e Å−3

Data collection: CrystalClear (Rigaku, 2007 ▶); cell refinement: CrystalClear; data reduction: CrystalClear; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: ORTEX (McArdle, 1995 ▶); software used to prepare material for publication: SHELXL97.

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S1600536811052421/ff2042sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536811052421/ff2042Isup2.hkl

Supplementary material file. DOI: 10.1107/S1600536811052421/ff2042Isup3.cml

Additional supplementary materials: crystallographic information; 3D view; checkCIF report

C16H19N3O5S	F(000) = 768.0
Mr = 365.41	Dx = 1.335 Mg m−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 5508 reflections
a = 16.861 (3) Å	θ = 3.0–27.5°
b = 11.317 (2) Å	µ = 0.21 mm−1
c = 9.6484 (19) Å	T = 293 K
β = 98.94 (3)°	Prism, colourless
V = 1818.7 (6) Å3	0.54 × 0.33 × 0.12 mm
Z = 4

Rigaku Saturn 724 CCD area-detector diffractometer	4176 independent reflections
Radiation source: fine-focus sealed tube	3718 reflections with I > 2σ(I)
graphite	Rint = 0.054
Detector resolution: 28.5714 pixels mm-1	θmax = 27.5°, θmin = 3.0°
dtprofit.ref scans	h = −20→21
Absorption correction: numerical (NUMABS; Higashi, 2000)	k = −14→14
Tmin = 0.921, Tmax = 0.975	l = −12→12
14817 measured reflections

Refinement on F2	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.083	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.180	H-atom parameters constrained
S = 1.26	w = 1/[σ2(Fo2) + (0.0486P)2 + 1.240P] where P = (Fo2 + 2Fc2)/3
4176 reflections	(Δ/σ)max < 0.001
230 parameters	Δρmax = 0.34 e Å−3
0 restraints	Δρmin = −0.23 e Å−3

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.

	x	y	z	Uiso*/Ueq
S1	0.36614 (4)	0.72248 (7)	0.16296 (8)	0.0467 (2)
O3	0.05637 (13)	0.7065 (2)	−0.3160 (2)	0.0637 (7)
O4	−0.06380 (16)	0.6314 (3)	−0.0995 (3)	0.0789 (8)
O2	0.49650 (13)	0.7178 (2)	0.3633 (2)	0.0574 (6)
O1	0.60458 (12)	0.59926 (19)	0.3591 (2)	0.0479 (5)
O5	−0.16027 (18)	0.7431 (4)	−0.2127 (5)	0.1271 (15)
N1	0.50500 (13)	0.5954 (2)	0.1795 (2)	0.0415 (6)
H1	0.5363	0.5490	0.1426	0.050*
N2	0.40231 (13)	0.5568 (2)	−0.0059 (2)	0.0377 (5)
N3	0.05095 (15)	0.7905 (3)	−0.1077 (3)	0.0524 (7)
H3	0.0756	0.8095	−0.0259	0.063*
C9	0.21789 (16)	0.7285 (3)	−0.0217 (3)	0.0431 (7)
H9	0.1985	0.7890	0.0290	0.052*
C3	0.5917 (3)	0.5968 (4)	0.6084 (4)	0.0761 (12)
H3A	0.5441	0.6448	0.5945	0.114*
H3B	0.6199	0.6089	0.7017	0.114*
H3C	0.5770	0.5151	0.5962	0.114*
C15	−0.0922 (2)	0.7299 (4)	−0.1594 (4)	0.0696 (11)
C16	−0.1190 (3)	0.5336 (5)	−0.1009 (7)	0.133 (2)
H16A	−0.1640	0.5574	−0.0578	0.199*
H16B	−0.0922	0.4684	−0.0498	0.199*
H16C	−0.1373	0.5100	−0.1960	0.199*
C1	0.7200 (2)	0.5557 (4)	0.5209 (4)	0.0855 (14)
H1A	0.7053	0.4740	0.5087	0.128*
H1B	0.7497	0.5673	0.6132	0.128*
H1C	0.7526	0.5781	0.4521	0.128*
C6	0.43024 (16)	0.6160 (2)	0.1075 (3)	0.0372 (6)
C7	0.32479 (16)	0.5921 (2)	−0.0557 (3)	0.0363 (6)
C10	0.17080 (16)	0.6823 (3)	−0.1401 (3)	0.0409 (6)
C8	0.29461 (16)	0.6830 (2)	0.0201 (3)	0.0384 (6)
C12	0.27640 (17)	0.5443 (3)	−0.1727 (3)	0.0427 (7)
H12	0.2951	0.4828	−0.2228	0.051*
C11	0.20071 (17)	0.5895 (3)	−0.2130 (3)	0.0440 (7)
H11	0.1684	0.5575	−0.2909	0.053*
C13	0.08877 (18)	0.7271 (3)	−0.1946 (3)	0.0460 (7)
C5	0.53326 (17)	0.6445 (3)	0.3083 (3)	0.0419 (6)
C4	0.64493 (19)	0.6309 (3)	0.5033 (3)	0.0484 (7)
C14	−0.03095 (19)	0.8269 (4)	−0.1511 (4)	0.0637 (10)
H14A	−0.0350	0.8638	−0.2427	0.076*
H14B	−0.0441	0.8864	−0.0860	0.076*
C2	0.6663 (2)	0.7601 (3)	0.5084 (4)	0.0668 (10)
H2A	0.6974	0.7777	0.4356	0.100*
H2B	0.6972	0.7785	0.5980	0.100*
H2C	0.6181	0.8065	0.4947	0.100*

	U11	U22	U33	U12	U13	U23
S1	0.0417 (4)	0.0507 (5)	0.0453 (4)	0.0087 (3)	−0.0005 (3)	−0.0150 (3)
O3	0.0521 (13)	0.096 (2)	0.0399 (12)	0.0100 (13)	−0.0022 (10)	−0.0002 (12)
O4	0.0595 (16)	0.095 (2)	0.0791 (18)	−0.0064 (15)	0.0023 (14)	0.0225 (16)
O2	0.0514 (13)	0.0652 (15)	0.0529 (13)	0.0140 (11)	−0.0002 (10)	−0.0218 (11)
O1	0.0480 (11)	0.0523 (13)	0.0397 (11)	0.0121 (9)	−0.0045 (9)	−0.0131 (9)
O5	0.0533 (18)	0.141 (3)	0.172 (4)	0.0003 (19)	−0.029 (2)	0.035 (3)
N1	0.0374 (12)	0.0463 (14)	0.0399 (12)	0.0078 (10)	0.0028 (10)	−0.0081 (10)
N2	0.0387 (12)	0.0367 (12)	0.0376 (12)	0.0003 (9)	0.0053 (10)	−0.0051 (10)
N3	0.0409 (14)	0.0684 (19)	0.0456 (14)	0.0096 (12)	−0.0003 (11)	−0.0011 (13)
C9	0.0388 (15)	0.0472 (17)	0.0439 (15)	0.0045 (12)	0.0080 (12)	−0.0043 (13)
C3	0.103 (3)	0.079 (3)	0.0425 (19)	−0.007 (2)	0.003 (2)	0.0012 (19)
C15	0.0423 (19)	0.099 (3)	0.065 (2)	0.0063 (19)	0.0001 (16)	0.007 (2)
C16	0.097 (4)	0.135 (5)	0.160 (6)	−0.038 (4)	0.000 (4)	0.054 (5)
C1	0.085 (3)	0.092 (3)	0.067 (2)	0.040 (2)	−0.029 (2)	−0.028 (2)
C6	0.0377 (14)	0.0371 (14)	0.0367 (14)	0.0016 (11)	0.0049 (11)	−0.0013 (11)
C7	0.0362 (14)	0.0352 (14)	0.0377 (14)	−0.0004 (11)	0.0064 (11)	−0.0003 (11)
C10	0.0381 (14)	0.0473 (17)	0.0374 (14)	−0.0010 (12)	0.0064 (11)	0.0013 (12)
C8	0.0372 (14)	0.0384 (15)	0.0392 (14)	0.0007 (11)	0.0050 (11)	−0.0016 (12)
C12	0.0445 (16)	0.0406 (16)	0.0428 (15)	0.0016 (12)	0.0059 (12)	−0.0043 (13)
C11	0.0441 (16)	0.0492 (17)	0.0371 (14)	−0.0039 (13)	0.0013 (12)	−0.0023 (13)
C13	0.0409 (16)	0.0563 (19)	0.0400 (15)	0.0027 (13)	0.0037 (12)	0.0069 (14)
C5	0.0397 (15)	0.0447 (16)	0.0407 (15)	0.0016 (12)	0.0048 (12)	−0.0061 (13)
C4	0.0539 (18)	0.0501 (18)	0.0372 (15)	0.0083 (14)	−0.0057 (13)	−0.0104 (13)
C14	0.0473 (18)	0.074 (3)	0.067 (2)	0.0189 (17)	0.0000 (16)	0.0019 (19)
C2	0.065 (2)	0.059 (2)	0.071 (2)	−0.0095 (17)	−0.0060 (18)	−0.0116 (19)

S1—C8	1.742 (3)	C3—H3C	0.9600
S1—C6	1.757 (3)	C15—C14	1.501 (6)
O3—C13	1.235 (4)	C16—H16A	0.9600
O4—C15	1.312 (5)	C16—H16B	0.9600
O4—C16	1.444 (5)	C16—H16C	0.9600
O2—C5	1.207 (3)	C1—C4	1.513 (4)
O1—C5	1.329 (3)	C1—H1A	0.9600
O1—C4	1.494 (3)	C1—H1B	0.9600
O5—C15	1.191 (4)	C1—H1C	0.9600
N1—C6	1.362 (3)	C7—C12	1.395 (4)
N1—C5	1.377 (3)	C7—C8	1.403 (4)
N1—H1	0.8600	C10—C11	1.401 (4)
N2—C6	1.307 (3)	C10—C13	1.490 (4)
N2—C7	1.380 (3)	C12—C11	1.373 (4)
N3—C13	1.338 (4)	C12—H12	0.9300
N3—C14	1.440 (4)	C11—H11	0.9300
N3—H3	0.8600	C4—C2	1.505 (5)
C9—C10	1.389 (4)	C14—H14A	0.9700
C9—C8	1.393 (4)	C14—H14B	0.9700
C9—H9	0.9300	C2—H2A	0.9600
C3—C4	1.506 (5)	C2—H2B	0.9600
C3—H3A	0.9600	C2—H2C	0.9600
C3—H3B	0.9600
C8—S1—C6	88.06 (13)	N2—C7—C8	115.6 (2)
C15—O4—C16	117.2 (3)	C12—C7—C8	119.5 (2)
C5—O1—C4	120.4 (2)	C9—C10—C11	119.4 (3)
C6—N1—C5	123.7 (2)	C9—C10—C13	122.9 (3)
C6—N1—H1	118.2	C11—C10—C13	117.7 (3)
C5—N1—H1	118.2	C9—C8—C7	121.1 (3)
C6—N2—C7	110.0 (2)	C9—C8—S1	129.2 (2)
C13—N3—C14	120.0 (3)	C7—C8—S1	109.7 (2)
C13—N3—H3	120.0	C11—C12—C7	119.0 (3)
C14—N3—H3	120.0	C11—C12—H12	120.5
C10—C9—C8	119.1 (3)	C7—C12—H12	120.5
C10—C9—H9	120.5	C12—C11—C10	121.9 (3)
C8—C9—H9	120.5	C12—C11—H11	119.1
C4—C3—H3A	109.5	C10—C11—H11	119.1
C4—C3—H3B	109.5	O3—C13—N3	120.8 (3)
H3A—C3—H3B	109.5	O3—C13—C10	121.3 (3)
C4—C3—H3C	109.5	N3—C13—C10	117.9 (3)
H3A—C3—H3C	109.5	O2—C5—O1	126.9 (3)
H3B—C3—H3C	109.5	O2—C5—N1	123.0 (3)
O5—C15—O4	123.9 (4)	O1—C5—N1	110.1 (2)
O5—C15—C14	122.7 (4)	O1—C4—C2	109.6 (3)
O4—C15—C14	113.4 (3)	O1—C4—C3	109.4 (3)
O4—C16—H16A	109.5	C2—C4—C3	113.1 (3)
O4—C16—H16B	109.5	O1—C4—C1	102.8 (2)
H16A—C16—H16B	109.5	C2—C4—C1	110.5 (3)
O4—C16—H16C	109.5	C3—C4—C1	110.9 (3)
H16A—C16—H16C	109.5	N3—C14—C15	115.3 (3)
H16B—C16—H16C	109.5	N3—C14—H14A	108.4
C4—C1—H1A	109.5	C15—C14—H14A	108.4
C4—C1—H1B	109.5	N3—C14—H14B	108.4
H1A—C1—H1B	109.5	C15—C14—H14B	108.4
C4—C1—H1C	109.5	H14A—C14—H14B	107.5
H1A—C1—H1C	109.5	C4—C2—H2A	109.5
H1B—C1—H1C	109.5	C4—C2—H2B	109.5
N2—C6—N1	121.6 (2)	H2A—C2—H2B	109.5
N2—C6—S1	116.6 (2)	C4—C2—H2C	109.5
N1—C6—S1	121.8 (2)	H2A—C2—H2C	109.5
N2—C7—C12	124.9 (2)	H2B—C2—H2C	109.5
C16—O4—C15—O5	0.7 (7)	C8—C7—C12—C11	1.5 (4)
C16—O4—C15—C14	179.2 (4)	C7—C12—C11—C10	0.1 (4)
C7—N2—C6—N1	178.2 (2)	C9—C10—C11—C12	−1.6 (5)
C7—N2—C6—S1	−1.2 (3)	C13—C10—C11—C12	178.3 (3)
C5—N1—C6—N2	−171.5 (3)	C14—N3—C13—O3	5.3 (5)
C5—N1—C6—S1	7.8 (4)	C14—N3—C13—C10	−174.5 (3)
C8—S1—C6—N2	0.2 (2)	C9—C10—C13—O3	161.8 (3)
C8—S1—C6—N1	−179.1 (3)	C11—C10—C13—O3	−18.2 (5)
C6—N2—C7—C12	−178.0 (3)	C9—C10—C13—N3	−18.4 (5)
C6—N2—C7—C8	1.8 (3)	C11—C10—C13—N3	161.7 (3)
C8—C9—C10—C11	1.4 (4)	C4—O1—C5—O2	5.0 (5)
C8—C9—C10—C13	−178.6 (3)	C4—O1—C5—N1	−174.9 (2)
C10—C9—C8—C7	0.3 (4)	C6—N1—C5—O2	−6.2 (5)
C10—C9—C8—S1	−179.6 (2)	C6—N1—C5—O1	173.7 (3)
N2—C7—C8—C9	178.4 (3)	C5—O1—C4—C2	−65.7 (4)
C12—C7—C8—C9	−1.8 (4)	C5—O1—C4—C3	58.8 (4)
N2—C7—C8—S1	−1.7 (3)	C5—O1—C4—C1	176.7 (3)
C12—C7—C8—S1	178.2 (2)	C13—N3—C14—C15	71.6 (4)
C6—S1—C8—C9	−179.3 (3)	O5—C15—C14—N3	−168.8 (4)
C6—S1—C8—C7	0.8 (2)	O4—C15—C14—N3	12.7 (5)
N2—C7—C12—C11	−178.6 (3)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1···N2i	0.86	2.16	3.005 (3)	167.
N3—H3···O3ii	0.86	2.11	2.802 (3)	137.

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1⋯N2i	0.86	2.16	3.005 (3)	167
N3—H3⋯O3ii	0.86	2.11	2.802 (3)	137

Symmetry codes: (i) ; (ii) .