The crystal structure of the title compound, C
10H
11N
3O
4S
2, an inactive dithiazine analogue of 3-alkylamino-4
H-1,2,4-benzothiadiazine 1,1-dioxides that are known to be pancreatic B-cell selective K
ATP 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
CCDC reference: 225770
Key indicators
- Single-crystal X-ray study
- T = 293 K
- Mean (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
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
C10H11N3O4S2 | F(000) = 624 |
Mr = 301.34 | Dx = 1.531 Mg m−3 |
Monoclinic, P21/n | Cu Kα radiation, λ = 1.54180 Å |
Hall symbol: -P 2yn | Cell parameters from 31 reflections |
a = 7.4143 (7) Å | θ = 34.1–41.5° |
b = 21.461 (4) Å | µ = 3.85 mm−1 |
c = 8.3958 (11) Å | T = 293 K |
β = 101.840 (12)° | Prism, colourless |
V = 1307.5 (3) Å3 | 0.68 × 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 tube | Rint = 0.044 |
Graphite monochromator | θmax = 67.9°, θmin = 4.1° |
ω scans | h = −8→0 |
Absorption correction: ψ scan (EMPIR; Stoe & Cie, 1987) | k = 0→25 |
Tmin = 0.137, Tmax = 0.270 | l = −9→10 |
2498 measured reflections | 2 standard reflections every 60 min |
2317 independent reflections | intensity decay: 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)] = 0.052 | H 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 reflections | Δρmax = 0.44 e Å−3 |
178 parameters | Δρmin = −0.57 e Å−3 |
0 restraints | Extinction correction: SHELXL97, Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4 |
Primary atom site location: structure-invariant direct methods | Extinction 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 | x | y | z | Uiso*/Ueq | |
S1 | 0.22976 (9) | 0.09769 (3) | 0.11063 (8) | 0.0417 (3) | |
N2 | 0.3981 (3) | 0.14534 (10) | 0.1511 (3) | 0.0459 (6) | |
C3 | 0.5667 (4) | 0.12775 (13) | 0.1460 (3) | 0.0430 (6) | |
S4 | 0.65181 (9) | 0.05028 (3) | 0.15770 (9) | 0.0479 (3) | |
C5 | 0.4841 (4) | 0.00923 (13) | 0.2358 (3) | 0.0425 (6) | |
C6 | 0.5389 (4) | −0.04736 (14) | 0.3117 (4) | 0.0505 (7) | |
H6 | 0.6600 | −0.0607 | 0.3214 | 0.061* | |
C7 | 0.4167 (4) | −0.08335 (15) | 0.3718 (4) | 0.0537 (7) | |
H7 | 0.4523 | −0.1217 | 0.4194 | 0.064* | |
C8 | 0.2376 (4) | −0.06151 (14) | 0.3606 (3) | 0.0452 (6) | |
C9 | 0.1786 (4) | −0.00546 (13) | 0.2874 (3) | 0.0437 (6) | |
H9 | 0.0589 | 0.0086 | 0.2823 | 0.052* | |
C10 | 0.3026 (3) | 0.02921 (12) | 0.2217 (3) | 0.0406 (6) | |
N11 | 0.6957 (3) | 0.16836 (11) | 0.1314 (3) | 0.0486 (6) | |
H11 | 0.798 (5) | 0.1592 (19) | 0.143 (4) | 0.058* | |
C12 | 0.6659 (4) | 0.23559 (13) | 0.1002 (4) | 0.0508 (7) | |
H12 | 0.5338 | 0.2427 | 0.0601 | 0.061* | |
C13 | 0.7255 (8) | 0.27127 (18) | 0.2564 (6) | 0.0918 (15) | |
H13A | 0.6584 | 0.2566 | 0.3354 | 0.138* | |
H13B | 0.7012 | 0.3148 | 0.2366 | 0.138* | |
H13C | 0.8551 | 0.2652 | 0.2970 | 0.138* | |
C14 | 0.7657 (7) | 0.2553 (2) | −0.0292 (6) | 0.0967 (15) | |
H14A | 0.8961 | 0.2515 | 0.0110 | 0.145* | |
H14B | 0.7358 | 0.2978 | −0.0586 | 0.145* | |
H14C | 0.7291 | 0.2291 | −0.1231 | 0.145* | |
N3 | 0.1082 (4) | −0.09914 (13) | 0.4297 (3) | 0.0554 (7) | |
O1 | 0.1917 (3) | 0.08075 (10) | −0.0577 (2) | 0.0548 (5) | |
O2 | 0.0799 (3) | 0.12379 (10) | 0.1739 (3) | 0.0563 (6) | |
O3 | −0.0370 (3) | −0.07592 (12) | 0.4450 (3) | 0.0640 (6) | |
O4 | 0.1545 (4) | −0.15259 (13) | 0.4707 (4) | 0.0868 (9) | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
S1 | 0.0373 (4) | 0.0340 (4) | 0.0531 (4) | 0.0036 (2) | 0.0077 (3) | 0.0022 (3) |
N2 | 0.0402 (12) | 0.0332 (11) | 0.0647 (14) | 0.0035 (9) | 0.0115 (10) | −0.0021 (10) |
C3 | 0.0454 (15) | 0.0340 (13) | 0.0485 (13) | −0.0013 (11) | 0.0068 (11) | −0.0049 (11) |
S4 | 0.0415 (4) | 0.0346 (4) | 0.0701 (5) | 0.0036 (3) | 0.0174 (3) | −0.0013 (3) |
C5 | 0.0397 (13) | 0.0374 (14) | 0.0505 (14) | 0.0030 (11) | 0.0094 (11) | −0.0033 (11) |
C6 | 0.0436 (15) | 0.0404 (15) | 0.0666 (17) | 0.0079 (12) | 0.0093 (13) | 0.0042 (13) |
C7 | 0.0522 (17) | 0.0412 (14) | 0.0653 (18) | 0.0041 (13) | 0.0064 (14) | 0.0058 (13) |
C8 | 0.0445 (14) | 0.0420 (14) | 0.0486 (14) | −0.0026 (12) | 0.0084 (11) | 0.0026 (12) |
C9 | 0.0413 (14) | 0.0382 (14) | 0.0508 (14) | 0.0000 (11) | 0.0078 (11) | −0.0019 (11) |
C10 | 0.0409 (13) | 0.0334 (13) | 0.0464 (13) | 0.0035 (11) | 0.0066 (10) | −0.0011 (10) |
N11 | 0.0398 (12) | 0.0347 (12) | 0.0714 (15) | −0.0005 (10) | 0.0115 (11) | 0.0021 (11) |
C12 | 0.0454 (15) | 0.0351 (14) | 0.0688 (18) | −0.0012 (12) | 0.0044 (13) | 0.0076 (13) |
C13 | 0.123 (4) | 0.046 (2) | 0.092 (3) | 0.001 (2) | −0.012 (3) | −0.0123 (19) |
C14 | 0.104 (3) | 0.078 (3) | 0.116 (4) | 0.010 (3) | 0.042 (3) | 0.040 (3) |
N3 | 0.0539 (15) | 0.0526 (15) | 0.0577 (14) | −0.0073 (12) | 0.0066 (11) | 0.0100 (11) |
O1 | 0.0609 (13) | 0.0482 (12) | 0.0518 (11) | 0.0017 (10) | 0.0034 (9) | 0.0029 (9) |
O2 | 0.0415 (11) | 0.0459 (12) | 0.0845 (14) | 0.0101 (9) | 0.0199 (10) | 0.0066 (11) |
O3 | 0.0532 (13) | 0.0689 (16) | 0.0716 (14) | −0.0041 (11) | 0.0166 (11) | 0.0075 (12) |
O4 | 0.0747 (17) | 0.0568 (15) | 0.131 (2) | 0.0000 (13) | 0.0253 (16) | 0.0353 (16) |
Geometric parameters (Å, º) top
S1—O1 | 1.430 (2) | C9—C10 | 1.382 (4) |
S1—O2 | 1.440 (2) | C9—H9 | 0.9300 |
S1—N2 | 1.595 (2) | N11—C12 | 1.475 (4) |
S1—C10 | 1.765 (3) | N11—H11 | 0.77 (4) |
N2—C3 | 1.315 (3) | C12—C14 | 1.496 (5) |
C3—N11 | 1.318 (4) | C12—C13 | 1.505 (5) |
C3—S4 | 1.774 (3) | C12—H12 | 0.9800 |
S4—C5 | 1.757 (3) | C13—H13A | 0.9600 |
C5—C6 | 1.393 (4) | C13—H13B | 0.9600 |
C5—C10 | 1.394 (3) | C13—H13C | 0.9600 |
C6—C7 | 1.364 (4) | C14—H14A | 0.9600 |
C6—H6 | 0.9300 | C14—H14B | 0.9600 |
C7—C8 | 1.393 (4) | C14—H14C | 0.9600 |
C7—H7 | 0.9300 | N3—O3 | 1.217 (4) |
C8—C9 | 1.381 (4) | N3—O4 | 1.226 (4) |
C8—N3 | 1.462 (4) | | |
| | | |
O1—S1—O2 | 116.91 (14) | C9—C10—S1 | 120.2 (2) |
O1—S1—N2 | 111.14 (13) | C5—C10—S1 | 119.1 (2) |
O2—S1—N2 | 107.54 (13) | C3—N11—C12 | 125.3 (3) |
O1—S1—C10 | 106.71 (12) | C3—N11—H11 | 122 (3) |
O2—S1—C10 | 107.74 (13) | C12—N11—H11 | 112 (3) |
N2—S1—C10 | 106.26 (12) | N11—C12—C14 | 109.1 (3) |
C3—N2—S1 | 121.10 (19) | N11—C12—C13 | 109.7 (3) |
N2—C3—N11 | 121.7 (3) | C14—C12—C13 | 112.9 (4) |
N2—C3—S4 | 126.7 (2) | N11—C12—H12 | 108.4 |
N11—C3—S4 | 111.6 (2) | C14—C12—H12 | 108.4 |
C5—S4—C3 | 102.69 (13) | C13—C12—H12 | 108.4 |
C6—C5—C10 | 119.5 (3) | C12—C13—H13A | 109.5 |
C6—C5—S4 | 116.5 (2) | C12—C13—H13B | 109.5 |
C10—C5—S4 | 124.0 (2) | H13A—C13—H13B | 109.5 |
C7—C6—C5 | 120.6 (3) | C12—C13—H13C | 109.5 |
C7—C6—H6 | 119.7 | H13A—C13—H13C | 109.5 |
C5—C6—H6 | 119.7 | H13B—C13—H13C | 109.5 |
C6—C7—C8 | 118.8 (3) | C12—C14—H14A | 109.5 |
C6—C7—H7 | 120.6 | C12—C14—H14B | 109.5 |
C8—C7—H7 | 120.6 | H14A—C14—H14B | 109.5 |
C9—C8—C7 | 122.2 (3) | C12—C14—H14C | 109.5 |
C9—C8—N3 | 119.0 (3) | H14A—C14—H14C | 109.5 |
C7—C8—N3 | 118.8 (3) | H14B—C14—H14C | 109.5 |
C8—C9—C10 | 118.1 (3) | O3—N3—O4 | 123.8 (3) |
C8—C9—H9 | 120.9 | O3—N3—C8 | 118.8 (3) |
C10—C9—H9 | 120.9 | O4—N3—C8 | 117.3 (3) |
C9—C10—C5 | 120.7 (2) | | |
| | | |
O1—S1—N2—C3 | −68.3 (3) | C6—C5—C10—C9 | 2.3 (4) |
O2—S1—N2—C3 | 162.6 (2) | S4—C5—C10—C9 | −179.6 (2) |
C10—S1—N2—C3 | 47.4 (3) | C6—C5—C10—S1 | −174.8 (2) |
S1—N2—C3—N11 | 159.7 (2) | S4—C5—C10—S1 | 3.3 (3) |
S1—N2—C3—S4 | −20.5 (4) | O1—S1—C10—C9 | −96.9 (2) |
N2—C3—S4—C5 | −16.7 (3) | O2—S1—C10—C9 | 29.4 (3) |
N11—C3—S4—C5 | 163.1 (2) | N2—S1—C10—C9 | 144.4 (2) |
C3—S4—C5—C6 | −158.4 (2) | O1—S1—C10—C5 | 80.2 (2) |
C3—S4—C5—C10 | 23.5 (3) | O2—S1—C10—C5 | −153.5 (2) |
C10—C5—C6—C7 | 0.1 (4) | N2—S1—C10—C5 | −38.5 (2) |
S4—C5—C6—C7 | −178.1 (2) | N2—C3—N11—C12 | −7.5 (5) |
C5—C6—C7—C8 | −2.0 (5) | S4—C3—N11—C12 | 172.7 (2) |
C6—C7—C8—C9 | 1.6 (5) | C3—N11—C12—C14 | −134.7 (4) |
C6—C7—C8—N3 | −178.1 (3) | C3—N11—C12—C13 | 101.2 (4) |
C7—C8—C9—C10 | 0.8 (4) | C9—C8—N3—O3 | −12.0 (4) |
N3—C8—C9—C10 | −179.5 (2) | C7—C8—N3—O3 | 167.7 (3) |
C8—C9—C10—C5 | −2.8 (4) | C9—C8—N3—O4 | 168.9 (3) |
C8—C9—C10—S1 | 174.3 (2) | C7—C8—N3—O4 | −11.5 (4) |
Hydrogen-bond geometry (Å, º) top
D—H···A | D—H | H···A | D···A | D—H···A |
N11—H11···O2i | 0.77 (4) | 2.19 (4) | 2.957 (3) | 175 (4) |
Symmetry code: (i) x+1, y, z. |