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The crystal structure of the title compound, C10H11N3O4S2, an inactive di­thia­zine analogue of 3-alkyl­amino-4H-1,2,4-benzo­thia­diazine 1,1-dioxides that are known to be pancreatic B-cell selective KATP channel openers, reveals that the exocyclic NH group and the alkyl chain are oriented in the same spatial direction as in the active thia­diazine derivatives. The lack of activity is probably the result of the replacement of the NH group in the 4-position by an S atom. The crystal packing involves one N—H...O hydrogen bond.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536803020324/dn6092sup1.cif
Contains datablocks II, global

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536803020324/dn6092IIsup2.hkl
Contains datablock II

CCDC reference: 225770

Key indicators

  • Single-crystal X-ray study
  • T = 293 K
  • Mean [sigma](C-C) = 0.005 Å
  • R factor = 0.052
  • wR factor = 0.156
  • Data-to-parameter ratio = 13.0

checkCIF/PLATON results

No syntax errors found



Alert level A PLAT029_ALERT_3_A _diffrn_measured_fraction_theta_full Low ....... 0.98 PLAT052_ALERT_1_A (Proper) Absorption Correction Method Missing .. ? PLAT057_ALERT_3_A Correction for Absorption Required RT(exp) = 2.08
Alert level C PLAT063_ALERT_3_C Crystal Probably too Large for Beam Size ....... 0.68 mm PLAT242_ALERT_2_C Check Low U(eq) as Compared to Neighbors .... C12 PLAT340_ALERT_3_C Low Bond Precision on C-C bonds (x 1000) Ang ... 5
3 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 1 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 4 ALERT type 3 Indicator that the structure quality may be low 0 ALERT type 4 Improvement, methodology, query or suggestion

Computing details top

Data collection: DIF4 (Stoe & Cie, 1987); cell refinement: DIF4; data reduction: REDU4 (Stoe & Cie, 1987); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEPIII (Burnett & Johnson, 1996); software used to prepare material for publication: SHELXL97.

3-isopropylamino-7-nitro-1,4,2-benzothiadiazine 1,1-dioxide top
Crystal data top
C10H11N3O4S2F(000) = 624
Mr = 301.34Dx = 1.531 Mg m3
Monoclinic, P21/nCu Kα radiation, λ = 1.54180 Å
Hall symbol: -P 2ynCell parameters from 31 reflections
a = 7.4143 (7) Åθ = 34.1–41.5°
b = 21.461 (4) ŵ = 3.85 mm1
c = 8.3958 (11) ÅT = 293 K
β = 101.840 (12)°Prism, colourless
V = 1307.5 (3) Å30.68 × 0.53 × 0.34 mm
Z = 4
Data collection top
Stoe–Siemens AED four-circle
diffractometer
1955 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tubeRint = 0.044
Graphite monochromatorθmax = 67.9°, θmin = 4.1°
ω scansh = 80
Absorption correction: ψ scan
(EMPIR; Stoe & Cie, 1987)
k = 025
Tmin = 0.137, Tmax = 0.270l = 910
2498 measured reflections2 standard reflections every 60 min
2317 independent reflections intensity decay: 10%
Refinement top
Refinement on F2Secondary atom site location: difference Fourier map
Least-squares matrix: fullHydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.052H atoms treated by a mixture of independent and constrained refinement
wR(F2) = 0.156 w = 1/[σ2(Fo2) + (0.1169P)2 + 0.1969P]
where P = (Fo2 + 2Fc2)/3
S = 1.08(Δ/σ)max < 0.001
2317 reflectionsΔρmax = 0.44 e Å3
178 parametersΔρmin = 0.57 e Å3
0 restraintsExtinction correction: SHELXL97, Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
Primary atom site location: structure-invariant direct methodsExtinction coefficient: 0.0102 (13)
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
xyzUiso*/Ueq
S10.22976 (9)0.09769 (3)0.11063 (8)0.0417 (3)
N20.3981 (3)0.14534 (10)0.1511 (3)0.0459 (6)
C30.5667 (4)0.12775 (13)0.1460 (3)0.0430 (6)
S40.65181 (9)0.05028 (3)0.15770 (9)0.0479 (3)
C50.4841 (4)0.00923 (13)0.2358 (3)0.0425 (6)
C60.5389 (4)0.04736 (14)0.3117 (4)0.0505 (7)
H60.66000.06070.32140.061*
C70.4167 (4)0.08335 (15)0.3718 (4)0.0537 (7)
H70.45230.12170.41940.064*
C80.2376 (4)0.06151 (14)0.3606 (3)0.0452 (6)
C90.1786 (4)0.00546 (13)0.2874 (3)0.0437 (6)
H90.05890.00860.28230.052*
C100.3026 (3)0.02921 (12)0.2217 (3)0.0406 (6)
N110.6957 (3)0.16836 (11)0.1314 (3)0.0486 (6)
H110.798 (5)0.1592 (19)0.143 (4)0.058*
C120.6659 (4)0.23559 (13)0.1002 (4)0.0508 (7)
H120.53380.24270.06010.061*
C130.7255 (8)0.27127 (18)0.2564 (6)0.0918 (15)
H13A0.65840.25660.33540.138*
H13B0.70120.31480.23660.138*
H13C0.85510.26520.29700.138*
C140.7657 (7)0.2553 (2)0.0292 (6)0.0967 (15)
H14A0.89610.25150.01100.145*
H14B0.73580.29780.05860.145*
H14C0.72910.22910.12310.145*
N30.1082 (4)0.09914 (13)0.4297 (3)0.0554 (7)
O10.1917 (3)0.08075 (10)0.0577 (2)0.0548 (5)
O20.0799 (3)0.12379 (10)0.1739 (3)0.0563 (6)
O30.0370 (3)0.07592 (12)0.4450 (3)0.0640 (6)
O40.1545 (4)0.15259 (13)0.4707 (4)0.0868 (9)
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
S10.0373 (4)0.0340 (4)0.0531 (4)0.0036 (2)0.0077 (3)0.0022 (3)
N20.0402 (12)0.0332 (11)0.0647 (14)0.0035 (9)0.0115 (10)0.0021 (10)
C30.0454 (15)0.0340 (13)0.0485 (13)0.0013 (11)0.0068 (11)0.0049 (11)
S40.0415 (4)0.0346 (4)0.0701 (5)0.0036 (3)0.0174 (3)0.0013 (3)
C50.0397 (13)0.0374 (14)0.0505 (14)0.0030 (11)0.0094 (11)0.0033 (11)
C60.0436 (15)0.0404 (15)0.0666 (17)0.0079 (12)0.0093 (13)0.0042 (13)
C70.0522 (17)0.0412 (14)0.0653 (18)0.0041 (13)0.0064 (14)0.0058 (13)
C80.0445 (14)0.0420 (14)0.0486 (14)0.0026 (12)0.0084 (11)0.0026 (12)
C90.0413 (14)0.0382 (14)0.0508 (14)0.0000 (11)0.0078 (11)0.0019 (11)
C100.0409 (13)0.0334 (13)0.0464 (13)0.0035 (11)0.0066 (10)0.0011 (10)
N110.0398 (12)0.0347 (12)0.0714 (15)0.0005 (10)0.0115 (11)0.0021 (11)
C120.0454 (15)0.0351 (14)0.0688 (18)0.0012 (12)0.0044 (13)0.0076 (13)
C130.123 (4)0.046 (2)0.092 (3)0.001 (2)0.012 (3)0.0123 (19)
C140.104 (3)0.078 (3)0.116 (4)0.010 (3)0.042 (3)0.040 (3)
N30.0539 (15)0.0526 (15)0.0577 (14)0.0073 (12)0.0066 (11)0.0100 (11)
O10.0609 (13)0.0482 (12)0.0518 (11)0.0017 (10)0.0034 (9)0.0029 (9)
O20.0415 (11)0.0459 (12)0.0845 (14)0.0101 (9)0.0199 (10)0.0066 (11)
O30.0532 (13)0.0689 (16)0.0716 (14)0.0041 (11)0.0166 (11)0.0075 (12)
O40.0747 (17)0.0568 (15)0.131 (2)0.0000 (13)0.0253 (16)0.0353 (16)
Geometric parameters (Å, º) top
S1—O11.430 (2)C9—C101.382 (4)
S1—O21.440 (2)C9—H90.9300
S1—N21.595 (2)N11—C121.475 (4)
S1—C101.765 (3)N11—H110.77 (4)
N2—C31.315 (3)C12—C141.496 (5)
C3—N111.318 (4)C12—C131.505 (5)
C3—S41.774 (3)C12—H120.9800
S4—C51.757 (3)C13—H13A0.9600
C5—C61.393 (4)C13—H13B0.9600
C5—C101.394 (3)C13—H13C0.9600
C6—C71.364 (4)C14—H14A0.9600
C6—H60.9300C14—H14B0.9600
C7—C81.393 (4)C14—H14C0.9600
C7—H70.9300N3—O31.217 (4)
C8—C91.381 (4)N3—O41.226 (4)
C8—N31.462 (4)
O1—S1—O2116.91 (14)C9—C10—S1120.2 (2)
O1—S1—N2111.14 (13)C5—C10—S1119.1 (2)
O2—S1—N2107.54 (13)C3—N11—C12125.3 (3)
O1—S1—C10106.71 (12)C3—N11—H11122 (3)
O2—S1—C10107.74 (13)C12—N11—H11112 (3)
N2—S1—C10106.26 (12)N11—C12—C14109.1 (3)
C3—N2—S1121.10 (19)N11—C12—C13109.7 (3)
N2—C3—N11121.7 (3)C14—C12—C13112.9 (4)
N2—C3—S4126.7 (2)N11—C12—H12108.4
N11—C3—S4111.6 (2)C14—C12—H12108.4
C5—S4—C3102.69 (13)C13—C12—H12108.4
C6—C5—C10119.5 (3)C12—C13—H13A109.5
C6—C5—S4116.5 (2)C12—C13—H13B109.5
C10—C5—S4124.0 (2)H13A—C13—H13B109.5
C7—C6—C5120.6 (3)C12—C13—H13C109.5
C7—C6—H6119.7H13A—C13—H13C109.5
C5—C6—H6119.7H13B—C13—H13C109.5
C6—C7—C8118.8 (3)C12—C14—H14A109.5
C6—C7—H7120.6C12—C14—H14B109.5
C8—C7—H7120.6H14A—C14—H14B109.5
C9—C8—C7122.2 (3)C12—C14—H14C109.5
C9—C8—N3119.0 (3)H14A—C14—H14C109.5
C7—C8—N3118.8 (3)H14B—C14—H14C109.5
C8—C9—C10118.1 (3)O3—N3—O4123.8 (3)
C8—C9—H9120.9O3—N3—C8118.8 (3)
C10—C9—H9120.9O4—N3—C8117.3 (3)
C9—C10—C5120.7 (2)
O1—S1—N2—C368.3 (3)C6—C5—C10—C92.3 (4)
O2—S1—N2—C3162.6 (2)S4—C5—C10—C9179.6 (2)
C10—S1—N2—C347.4 (3)C6—C5—C10—S1174.8 (2)
S1—N2—C3—N11159.7 (2)S4—C5—C10—S13.3 (3)
S1—N2—C3—S420.5 (4)O1—S1—C10—C996.9 (2)
N2—C3—S4—C516.7 (3)O2—S1—C10—C929.4 (3)
N11—C3—S4—C5163.1 (2)N2—S1—C10—C9144.4 (2)
C3—S4—C5—C6158.4 (2)O1—S1—C10—C580.2 (2)
C3—S4—C5—C1023.5 (3)O2—S1—C10—C5153.5 (2)
C10—C5—C6—C70.1 (4)N2—S1—C10—C538.5 (2)
S4—C5—C6—C7178.1 (2)N2—C3—N11—C127.5 (5)
C5—C6—C7—C82.0 (5)S4—C3—N11—C12172.7 (2)
C6—C7—C8—C91.6 (5)C3—N11—C12—C14134.7 (4)
C6—C7—C8—N3178.1 (3)C3—N11—C12—C13101.2 (4)
C7—C8—C9—C100.8 (4)C9—C8—N3—O312.0 (4)
N3—C8—C9—C10179.5 (2)C7—C8—N3—O3167.7 (3)
C8—C9—C10—C52.8 (4)C9—C8—N3—O4168.9 (3)
C8—C9—C10—S1174.3 (2)C7—C8—N3—O411.5 (4)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N11—H11···O2i0.77 (4)2.19 (4)2.957 (3)175 (4)
Symmetry code: (i) x+1, y, z.
 

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