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The mol­ecules of the title compound, C14H11ClN2O4S, are linked together into ribbons formed by weak C—H...O hydrogen bonds.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536801020694/na6116sup1.cif
Contains datablocks global, I

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536801020694/na6116Isup2.hkl
Contains datablock I

CCDC reference: 180546

Key indicators

  • Single-crystal X-ray study
  • T = 120 K
  • Mean [sigma](C-C) = 0.005 Å
  • R factor = 0.054
  • wR factor = 0.116
  • Data-to-parameter ratio = 13.5

checkCIF results

No syntax errors found

ADDSYM reports no extra symmetry


Red Alert Alert Level A:
REFLT_03 From the CIF: _diffrn_reflns_theta_max 27.42 From the CIF: _reflns_number_total 2714 TEST2: Reflns within _diffrn_reflns_theta_max Count of symmetry unique reflns 3229 Completeness (_total/calc) 84.05% Alert A: < 85% complete (theta max?)
Author response: ...As can be seen the crystal is a very thin plate and this probably contributes to the difficulty. Experience shows that crystals of materials of this class of compound produce in many cases very small crystals and that re-crystallisation does not help.

1 Alert Level A = Potentially serious problem
0 Alert Level B = Potential problem
0 Alert Level C = Please check

Comment top

The title compound, (I), is a benzothiazole derivative prepared in our search for biologically active molecules by a similar procedure to that reported previously for GURGIP (Cannon et al., 2001; Cambridge Structural Database, Allen & Kennard, 1993)

GURGIP and compound (I) have similar molecular structures but have totally different supramolecular structures.

GURGIP has a supramolecular structure consisting of base-paired dimers with an R22(12) motif formed by a centrosymmetrically related pair of N—H···O hydrogen bonds.

Compound (I) has one intramolecular hydrogen bond, N21–H21···O14, which forms an R(6) ring, Bernstein et al. (1995). The molecules are linked together into ribbons formed by the weak hydrogen bonds, C5–H5···O16 and C7–H7···O14. These two bonds combine to form a C22(10) chain. These hydrogen bonds link the molecules head-to-tail as a result of the centres of symmetry at (1, 0, 1/2) for the former bond and (1/2, 0, 1) for the latter bond forming in each case R22(22) rings and hence forming ribbons (Fig. 2). The details of the hydrogen bonding are given in Table 1.

Examination of the structure with PLATON (Spek, 2001) showed that there were no solvent accessible voids in the crystal lattice.

Experimental top

A solution of Meldrum's acid (3.45 mmol) and trimethyl orthoformate (17.3 mmol) was heated to reflux for 2.5 h, then 2-amino-6-chlorobenzothiazole (3.45 mmol) was added and the reaction mixture was heated for a further 30 min. The title compound precipitated, was separated by filtration, and recrystallized form ethanol, affording crystals suitable for X-ray diffraction (m.p.: 524 K, yield: 65%).

Refinement top

H atoms were treated as riding atoms with C—H = 0.95–0.98 Å and N—H = 0.88 Å.

Computing details top

Data collection: KappaCCD Server Software (Nonius, 1997); cell refinement: DENZO-SMN (Otwinowski & Minor, 1997); data reduction: DENZO-SMN; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEPII (Johnson, 1976) and PLATON (Spek, 2001); software used to prepare material for publication: SHELXL97 and WORDPERFECT macro PRPKAPPA (Ferguson, 1999).

Figures top
[Figure 1] Fig. 1. A view of (I) with the atomic numbering scheme. Displacement ellipsoids are drawn at the 30% probability level.
[Figure 2] Fig. 2. A view of the crystal structure showing the C22(10) chains and the two R22(22) rings. The molecule labelled with an asterisk (*) is at (2 - x, -y, 1 - z) and that labelled with a hash (#) is at (1 - x, -y, 2 - z).
5-[(6-Chloro-[1,3]benzothiazol-2-ylamino)-methylene]-2,2-dimethyl- [1,3]dioxane-4,6-dione top
Crystal data top
C14H11ClN2O4SDx = 1.583 Mg m3
Mr = 338.76Melting point: 524K K
Monoclinic, P21/cMo Kα radiation, λ = 0.71073 Å
a = 5.3389 (4) ÅCell parameters from 2714 reflections
b = 28.583 (2) Åθ = 3.1–27.4°
c = 9.8618 (8) ŵ = 0.44 mm1
β = 109.178 (4)°T = 120 K
V = 1421.41 (19) Å3Plate, yellow
Z = 40.20 × 0.15 × 0.01 mm
F(000) = 696
Data collection top
Nonius KappaCCD
diffractometer
2714 independent reflections
Radiation source: fine-focus sealed X-ray tube1430 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.066
ϕ scans, and ω scans with κ offsetsθmax = 27.4°, θmin = 3.1°
Absorption correction: multi-scan
(DENZO-SMN; Otwinowski & Minor, 1997)
h = 66
Tmin = 0.918, Tmax = 0.996k = 3729
6289 measured reflectionsl = 1212
Refinement top
Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.054Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.116H-atom parameters constrained
S = 0.94 w = 1/[σ2(Fo2) + (0.0358P)2]
where P = (Fo2 + 2Fc2)/3
2714 reflections(Δ/σ)max < 0.001
201 parametersΔρmax = 0.33 e Å3
0 restraintsΔρmin = 0.36 e Å3
Crystal data top
C14H11ClN2O4SV = 1421.41 (19) Å3
Mr = 338.76Z = 4
Monoclinic, P21/cMo Kα radiation
a = 5.3389 (4) ŵ = 0.44 mm1
b = 28.583 (2) ÅT = 120 K
c = 9.8618 (8) Å0.20 × 0.15 × 0.01 mm
β = 109.178 (4)°
Data collection top
Nonius KappaCCD
diffractometer
2714 independent reflections
Absorption correction: multi-scan
(DENZO-SMN; Otwinowski & Minor, 1997)
1430 reflections with I > 2σ(I)
Tmin = 0.918, Tmax = 0.996Rint = 0.066
6289 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0540 restraints
wR(F2) = 0.116H-atom parameters constrained
S = 0.94Δρmax = 0.33 e Å3
2714 reflectionsΔρmin = 0.36 e Å3
201 parameters
Special details top

Experimental. The program DENZO-SMN (Otwinowski & Minor, 1997) uses a scaling algorithm (Fox & Holmes, 1966) which effectively corrects for absorption effects. High redundancy data were used in the scaling program hence the 'multi-scan' code word was used. No transmission coefficients are available from the program (only scale factors for each frame). The scale factors in the experimental table are calculated from the 'size' command in the SHELXL97 input file.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
S10.50857 (17)0.02167 (3)0.82323 (11)0.0234 (3)
C20.7535 (7)0.01394 (13)0.7970 (4)0.0205 (9)
N210.8452 (5)0.05151 (10)0.8920 (3)0.0233 (8)
C221.0219 (6)0.08347 (12)0.8797 (4)0.0196 (9)
O111.3791 (4)0.18811 (9)1.0377 (3)0.0236 (6)
C121.1915 (7)0.20408 (13)1.1032 (4)0.0237 (10)
C1211.3431 (7)0.23615 (14)1.2231 (4)0.0408 (12)
C1220.9566 (7)0.22650 (13)0.9937 (4)0.0321 (11)
O131.1038 (5)0.16556 (9)1.1721 (3)0.0265 (7)
C141.0195 (7)0.12659 (13)1.0921 (4)0.0227 (10)
O140.8806 (5)0.09885 (9)1.1311 (3)0.0278 (7)
C151.1109 (6)0.12006 (12)0.9711 (4)0.0185 (9)
C161.3155 (7)0.14992 (13)0.9496 (4)0.0208 (9)
O161.4352 (5)0.14314 (8)0.8677 (3)0.0279 (7)
N30.8400 (5)0.00484 (10)0.6939 (3)0.0193 (8)
C3A0.7079 (6)0.03472 (13)0.6214 (4)0.0213 (9)
C40.7513 (7)0.05519 (13)0.5031 (4)0.0217 (9)
C50.6086 (7)0.09474 (13)0.4429 (4)0.0253 (10)
C60.4247 (7)0.11302 (13)0.5011 (4)0.0216 (9)
Cl60.24393 (19)0.16248 (3)0.41996 (11)0.0335 (3)
C70.3772 (6)0.09389 (13)0.6180 (4)0.0190 (9)
C7A0.5227 (7)0.05422 (12)0.6769 (4)0.0190 (9)
H210.78340.05440.96400.028*
H221.08870.08020.80200.024*
H12D1.49300.21921.28950.061*
H12E1.22580.24721.27480.061*
H12F1.40920.26301.18330.061*
H12A1.01520.25400.95280.048*
H12B0.82790.23611.03980.048*
H12C0.87350.20400.91710.048*
H40.87700.04220.46430.026*
H50.63600.10930.36230.030*
H70.25170.10710.65650.023*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
S10.0268 (6)0.0237 (6)0.0213 (6)0.0030 (4)0.0101 (4)0.0008 (5)
C20.021 (2)0.021 (2)0.021 (2)0.0008 (17)0.0090 (18)0.0018 (19)
N210.0256 (18)0.0274 (19)0.020 (2)0.0014 (15)0.0119 (15)0.0026 (16)
C220.018 (2)0.022 (2)0.022 (2)0.0045 (17)0.0114 (17)0.0082 (19)
O110.0258 (15)0.0235 (16)0.0243 (16)0.0049 (12)0.0120 (12)0.0067 (14)
C120.031 (2)0.026 (2)0.020 (2)0.0049 (18)0.0161 (19)0.005 (2)
C1210.055 (3)0.036 (3)0.043 (3)0.016 (2)0.032 (2)0.015 (2)
C1220.034 (2)0.026 (2)0.041 (3)0.0015 (19)0.018 (2)0.001 (2)
O130.0385 (16)0.0258 (16)0.0175 (15)0.0063 (13)0.0124 (12)0.0018 (14)
C140.021 (2)0.021 (2)0.023 (3)0.0024 (18)0.0024 (18)0.002 (2)
O140.0325 (16)0.0332 (18)0.0198 (16)0.0052 (13)0.0113 (12)0.0055 (14)
C150.024 (2)0.015 (2)0.017 (2)0.0007 (17)0.0070 (17)0.0002 (19)
C160.020 (2)0.021 (2)0.020 (2)0.0032 (18)0.0046 (18)0.003 (2)
O160.0309 (16)0.0318 (17)0.0287 (18)0.0043 (13)0.0203 (14)0.0070 (14)
N30.0190 (18)0.0162 (18)0.024 (2)0.0010 (13)0.0088 (15)0.0023 (16)
C3A0.020 (2)0.021 (2)0.021 (2)0.0042 (17)0.0036 (18)0.0054 (19)
C40.024 (2)0.024 (2)0.021 (2)0.0024 (17)0.0122 (17)0.007 (2)
C50.034 (2)0.023 (2)0.019 (2)0.0082 (19)0.0085 (19)0.001 (2)
C60.029 (2)0.017 (2)0.018 (2)0.0009 (17)0.0070 (18)0.0023 (19)
Cl60.0460 (7)0.0263 (6)0.0299 (7)0.0094 (5)0.0147 (5)0.0065 (5)
C70.023 (2)0.023 (2)0.018 (2)0.0007 (17)0.0147 (17)0.0065 (19)
C7A0.021 (2)0.019 (2)0.018 (2)0.0009 (17)0.0086 (17)0.0006 (19)
Geometric parameters (Å, º) top
S1—C7A1.740 (4)C122—H12C0.9800
S1—C21.742 (4)O13—C141.354 (4)
C2—N31.274 (4)C14—O141.230 (4)
C2—N211.403 (4)C14—C151.443 (5)
N21—C221.347 (4)C15—C161.456 (5)
N21—H210.8800C16—O161.199 (4)
C22—C151.360 (5)N3—C3A1.399 (4)
C22—H220.9500C3A—C41.391 (5)
O11—C161.367 (4)C3A—C7A1.394 (5)
O11—C121.433 (4)C4—C51.383 (5)
C12—O131.450 (4)C4—H40.9500
C12—C1221.503 (5)C5—C61.392 (5)
C12—C1211.505 (5)C5—H50.9500
C121—H12D0.9800C6—C71.372 (5)
C121—H12E0.9800C6—Cl61.750 (4)
C121—H12F0.9800C7—C7A1.389 (5)
C122—H12A0.9800C7—H70.9500
C122—H12B0.9800
C7A—S1—C287.14 (18)C14—O13—C12116.6 (3)
N3—C2—N21123.4 (3)O14—C14—O13117.9 (4)
N3—C2—S1119.1 (3)O14—C14—C15125.3 (4)
N21—C2—S1117.5 (3)O13—C14—C15116.8 (3)
C22—N21—C2124.1 (3)C22—C15—C14120.5 (3)
C22—N21—H21118.0C22—C15—C16118.0 (4)
C2—N21—H21118.0C14—C15—C16121.3 (3)
N21—C22—C15124.4 (4)O16—C16—O11118.8 (3)
N21—C22—H22117.8O16—C16—C15126.5 (4)
C15—C22—H22117.8O11—C16—C15114.6 (3)
C16—O11—C12118.5 (3)C2—N3—C3A108.6 (3)
O11—C12—O13110.5 (3)C4—C3A—C7A119.8 (3)
O11—C12—C122110.7 (3)C4—C3A—N3125.0 (4)
O13—C12—C122109.8 (3)C7A—C3A—N3115.2 (4)
O11—C12—C121105.9 (3)C5—C4—C3A118.9 (4)
O13—C12—C121105.5 (3)C5—C4—H4120.5
C122—C12—C121114.3 (3)C3A—C4—H4120.5
C12—C121—H12D109.5C4—C5—C6119.5 (4)
C12—C121—H12E109.5C4—C5—H5120.2
H12D—C121—H12E109.5C6—C5—H5120.2
C12—C121—H12F109.5C7—C6—C5123.2 (3)
H12D—C121—H12F109.5C7—C6—Cl6118.6 (3)
H12E—C121—H12F109.5C5—C6—Cl6118.2 (3)
C12—C122—H12A109.5C6—C7—C7A116.4 (4)
C12—C122—H12B109.5C6—C7—H7121.8
H12A—C122—H12B109.5C7A—C7—H7121.8
C12—C122—H12C109.5C7—C7A—C3A122.2 (4)
H12A—C122—H12C109.5C7—C7A—S1127.8 (3)
H12B—C122—H12C109.5C3A—C7A—S1110.0 (3)
C7A—S1—C2—N30.6 (3)C14—C15—C16—O16167.1 (4)
C7A—S1—C2—N21179.4 (3)C22—C15—C16—O11174.8 (3)
N3—C2—N21—C224.1 (5)C14—C15—C16—O1110.0 (5)
S1—C2—N21—C22175.9 (3)N21—C2—N3—C3A179.8 (3)
C2—N21—C22—C15179.8 (3)S1—C2—N3—C3A0.2 (4)
C16—O11—C12—O1350.3 (4)C2—N3—C3A—C4179.7 (3)
C16—O11—C12—C12271.6 (4)C2—N3—C3A—C7A0.4 (4)
C16—O11—C12—C121164.0 (3)C7A—C3A—C4—C50.0 (5)
O11—C12—O13—C1450.3 (4)N3—C3A—C4—C5179.2 (3)
C122—C12—O13—C1472.1 (4)C3A—C4—C5—C60.3 (5)
C121—C12—O13—C14164.3 (3)C4—C5—C6—C70.5 (6)
C12—O13—C14—O14160.9 (3)C4—C5—C6—Cl6178.9 (3)
C12—O13—C14—C1521.8 (4)C5—C6—C7—C7A0.5 (5)
N21—C22—C15—C140.7 (5)Cl6—C6—C7—C7A179.0 (3)
N21—C22—C15—C16175.9 (3)C6—C7—C7A—C3A0.2 (5)
O14—C14—C15—C227.3 (6)C6—C7—C7A—S1179.6 (3)
O13—C14—C15—C22175.7 (3)C4—C3A—C7A—C70.0 (5)
O14—C14—C15—C16167.7 (3)N3—C3A—C7A—C7179.3 (3)
O13—C14—C15—C169.3 (5)C4—C3A—C7A—S1179.9 (3)
C12—O11—C16—O16161.7 (3)N3—C3A—C7A—S10.9 (4)
C12—O11—C16—C1520.9 (4)C2—S1—C7A—C7179.4 (3)
C22—C15—C16—O168.0 (5)C2—S1—C7A—C3A0.8 (3)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N21—H21···O140.882.012.671 (4)131
C5—H5···O16i0.952.383.299 (5)163
C7—H7···O14ii0.952.433.205 (5)138
Symmetry codes: (i) x+2, y, z+1; (ii) x+1, y, z+2.

Experimental details

Crystal data
Chemical formulaC14H11ClN2O4S
Mr338.76
Crystal system, space groupMonoclinic, P21/c
Temperature (K)120
a, b, c (Å)5.3389 (4), 28.583 (2), 9.8618 (8)
β (°) 109.178 (4)
V3)1421.41 (19)
Z4
Radiation typeMo Kα
µ (mm1)0.44
Crystal size (mm)0.20 × 0.15 × 0.01
Data collection
DiffractometerNonius KappaCCD
diffractometer
Absorption correctionMulti-scan
(DENZO-SMN; Otwinowski & Minor, 1997)
Tmin, Tmax0.918, 0.996
No. of measured, independent and
observed [I > 2σ(I)] reflections
6289, 2714, 1430
Rint0.066
(sin θ/λ)max1)0.648
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.054, 0.116, 0.94
No. of reflections2714
No. of parameters201
H-atom treatmentH-atom parameters constrained
Δρmax, Δρmin (e Å3)0.33, 0.36

Computer programs: KappaCCD Server Software (Nonius, 1997), DENZO-SMN (Otwinowski & Minor, 1997), DENZO-SMN, SHELXS97 (Sheldrick, 1997), SHELXL97 (Sheldrick, 1997), ORTEPII (Johnson, 1976) and PLATON (Spek, 2001), SHELXL97 and WORDPERFECT macro PRPKAPPA (Ferguson, 1999).

Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N21—H21···O140.882.012.671 (4)131
C5—H5···O16i0.952.383.299 (5)163
C7—H7···O14ii0.952.433.205 (5)138
Symmetry codes: (i) x+2, y, z+1; (ii) x+1, y, z+2.
 

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