In the title compound, C
9H
11Cl
2N
3O
4S
2, systematic name 6-chloro-3-chloromethyl-3,4-dihydro-2-methyl-7-sulfamoyl-1,2,4-benzothiadiazine 1,1-dioxide, three kinds of N—H
O hydrogen bond generate a sheet structure. The combination of four N—H
O hydrogen bonds yields an
R44(26) ring, with adjacent rings linked into two-dimensional layers parallel to the (001) plane. Pairs of adjacent planes are further connected by N—H
O hydrogen bonds.
Supporting information
CCDC reference: 614861
Key indicators
- Single-crystal X-ray study
- T = 187 K
- Mean (C-C) = 0.003 Å
- R factor = 0.035
- wR factor = 0.092
- Data-to-parameter ratio = 15.4
checkCIF/PLATON results
No syntax errors found
Alert level C
PLAT220_ALERT_2_C Large Non-Solvent C Ueq(max)/Ueq(min) ... 2.59 Ratio
PLAT431_ALERT_2_C Short Inter HL..A Contact Cl1 .. O4 .. 3.24 Ang.
0 ALERT level A = In general: serious problem
0 ALERT level B = Potentially serious problem
2 ALERT level C = Check and explain
0 ALERT level G = General alerts; check
0 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
2 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
0 ALERT type 4 Improvement, methodology, query or suggestion
Data collection: SMART (Bruker, 1998); cell refinement: SMART; data reduction: SAINT (Bruker, 2003); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: SHELXTL (Bruker, 1997); software used to prepare material for publication: SHELXTL.
6-chloro-3-chloromethyl-3,4-dihydro-2-methyl-7-sulfamoyl-1,2,4-benzo-
thiadiazine 1,1-dioxide
top
Crystal data top
C9H11Cl2N3O4S2 | F(000) = 1472 |
Mr = 360.23 | Dx = 1.683 Mg m−3 |
Orthorhombic, Pbca | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: -P 2ac 2ab | Cell parameters from 8375 reflections |
a = 9.5251 (5) Å | θ = 2.6–26.0° |
b = 15.4476 (8) Å | µ = 0.77 mm−1 |
c = 19.3226 (11) Å | T = 187 K |
V = 2843.1 (3) Å3 | Prism, colourless |
Z = 8 | 0.41 × 0.24 × 0.22 mm |
Data collection top
Bruker APEX CCD area-detector diffractometer | 2794 independent reflections |
Radiation source: fine-focus sealed tube | 2624 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.021 |
φ and ω scans | θmax = 26.0°, θmin = 2.6° |
Absorption correction: multi-scan (SAINT; Bruker, 2003) | h = −11→11 |
Tmin = 0.746, Tmax = 0.849 | k = −19→19 |
14885 measured reflections | l = −19→23 |
Refinement top
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)] = 0.035 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.092 | H-atom parameters constrained |
S = 1.09 | w = 1/[σ2(Fo2) + (0.0457P)2 + 2.8362P] where P = (Fo2 + 2Fc2)/3 |
2794 reflections | (Δ/σ)max = 0.001 |
182 parameters | Δρmax = 0.62 e Å−3 |
0 restraints | Δρmin = −0.52 e Å−3 |
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 >
2σ(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 | |
C1 | 0.7656 (2) | 0.82837 (12) | 0.38950 (10) | 0.0197 (4) | |
C2 | 0.7237 (2) | 0.74982 (13) | 0.41979 (10) | 0.0196 (4) | |
C3 | 0.8117 (2) | 0.67988 (13) | 0.42417 (10) | 0.0211 (4) | |
H3 | 0.7788 | 0.6272 | 0.4437 | 0.025* | |
C4 | 0.9510 (2) | 0.68579 (13) | 0.39979 (10) | 0.0192 (4) | |
C5 | 0.9928 (2) | 0.76498 (13) | 0.36990 (10) | 0.0196 (4) | |
C6 | 0.9009 (2) | 0.83446 (13) | 0.36407 (10) | 0.0212 (4) | |
H6 | 0.9313 | 0.8865 | 0.3425 | 0.025* | |
C7 | 1.1880 (2) | 0.62354 (14) | 0.39110 (12) | 0.0281 (5) | |
H7 | 1.2332 | 0.6535 | 0.4312 | 0.034* | |
C8 | 1.2479 (3) | 0.53292 (15) | 0.38511 (16) | 0.0399 (6) | |
H8A | 1.2049 | 0.5028 | 0.3451 | 0.048* | |
H8B | 1.2257 | 0.4995 | 0.4275 | 0.048* | |
C9 | 1.1568 (3) | 0.63932 (19) | 0.26241 (14) | 0.0495 (7) | |
H9A | 1.2091 | 0.5868 | 0.2505 | 0.074* | |
H9B | 1.1673 | 0.6820 | 0.2253 | 0.074* | |
H9C | 1.0572 | 0.6251 | 0.2681 | 0.074* | |
Cl1 | 0.55442 (5) | 0.73820 (3) | 0.45138 (3) | 0.02725 (15) | |
Cl2 | 1.43385 (7) | 0.53842 (4) | 0.37383 (5) | 0.0560 (2) | |
N1 | 0.51817 (19) | 0.89465 (12) | 0.33766 (10) | 0.0281 (4) | |
H1A | 0.5387 | 0.8769 | 0.2931 | 0.034* | |
H1B | 0.4554 | 0.8620 | 0.3606 | 0.034* | |
N2 | 1.2120 (2) | 0.67555 (12) | 0.32766 (10) | 0.0289 (4) | |
N3 | 1.03804 (18) | 0.61601 (11) | 0.40418 (9) | 0.0240 (4) | |
H3A | 1.0086 | 0.5697 | 0.4275 | 0.029* | |
O1 | 0.73376 (16) | 0.98181 (10) | 0.34085 (8) | 0.0311 (4) | |
O2 | 0.60838 (18) | 0.94607 (10) | 0.44876 (8) | 0.0323 (4) | |
O3 | 1.17323 (17) | 0.82416 (11) | 0.27971 (9) | 0.0355 (4) | |
O4 | 1.25153 (16) | 0.80704 (10) | 0.39927 (8) | 0.0302 (4) | |
S1 | 0.65637 (5) | 0.92061 (3) | 0.38113 (3) | 0.02248 (14) | |
S2 | 1.16733 (5) | 0.77609 (3) | 0.34291 (3) | 0.02285 (14) | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
C1 | 0.0190 (9) | 0.0157 (9) | 0.0243 (10) | 0.0021 (8) | −0.0013 (7) | −0.0013 (7) |
C2 | 0.0174 (10) | 0.0208 (9) | 0.0208 (9) | −0.0023 (8) | 0.0017 (7) | −0.0018 (8) |
C3 | 0.0228 (10) | 0.0178 (9) | 0.0228 (9) | −0.0023 (8) | 0.0008 (8) | 0.0015 (7) |
C4 | 0.0185 (9) | 0.0188 (9) | 0.0203 (9) | 0.0000 (7) | −0.0025 (7) | −0.0014 (7) |
C5 | 0.0154 (9) | 0.0216 (10) | 0.0219 (9) | −0.0007 (8) | 0.0003 (7) | 0.0001 (7) |
C6 | 0.0195 (10) | 0.0188 (9) | 0.0252 (10) | −0.0017 (8) | −0.0012 (8) | 0.0015 (8) |
C7 | 0.0220 (10) | 0.0235 (11) | 0.0388 (12) | 0.0050 (9) | 0.0019 (9) | 0.0034 (9) |
C8 | 0.0264 (12) | 0.0236 (12) | 0.0696 (18) | 0.0027 (10) | 0.0030 (12) | −0.0015 (11) |
C9 | 0.067 (2) | 0.0480 (16) | 0.0341 (14) | 0.0000 (14) | 0.0109 (13) | −0.0133 (12) |
Cl1 | 0.0195 (3) | 0.0269 (3) | 0.0354 (3) | −0.00072 (19) | 0.00791 (19) | 0.0017 (2) |
Cl2 | 0.0245 (3) | 0.0316 (3) | 0.1120 (7) | 0.0078 (2) | 0.0058 (3) | −0.0080 (4) |
N1 | 0.0199 (9) | 0.0320 (10) | 0.0324 (10) | 0.0025 (8) | 0.0009 (7) | 0.0025 (8) |
N2 | 0.0263 (10) | 0.0266 (9) | 0.0338 (10) | 0.0044 (8) | 0.0085 (8) | −0.0002 (8) |
N3 | 0.0217 (9) | 0.0179 (8) | 0.0323 (9) | 0.0013 (7) | 0.0024 (7) | 0.0031 (7) |
O1 | 0.0265 (8) | 0.0221 (8) | 0.0447 (9) | 0.0022 (6) | 0.0044 (7) | 0.0082 (7) |
O2 | 0.0394 (10) | 0.0255 (8) | 0.0321 (8) | 0.0079 (7) | 0.0047 (7) | −0.0037 (6) |
O3 | 0.0285 (8) | 0.0410 (9) | 0.0369 (9) | 0.0026 (7) | 0.0075 (7) | 0.0157 (7) |
O4 | 0.0195 (7) | 0.0284 (8) | 0.0428 (9) | −0.0036 (6) | −0.0027 (7) | 0.0004 (7) |
S1 | 0.0207 (3) | 0.0176 (3) | 0.0292 (3) | 0.00320 (19) | 0.00205 (19) | 0.00099 (19) |
S2 | 0.0163 (3) | 0.0237 (3) | 0.0286 (3) | 0.00057 (18) | 0.00289 (19) | 0.0051 (2) |
Geometric parameters (Å, º) top
C1—C6 | 1.383 (3) | C8—Cl2 | 1.787 (3) |
C1—C2 | 1.405 (3) | C8—H8A | 0.9900 |
C1—S1 | 1.771 (2) | C8—H8B | 0.9900 |
C2—C3 | 1.370 (3) | C9—N2 | 1.477 (3) |
C2—Cl1 | 1.7334 (19) | C9—H9A | 0.9800 |
C3—C4 | 1.411 (3) | C9—H9B | 0.9800 |
C3—H3 | 0.9500 | C9—H9C | 0.9800 |
C4—N3 | 1.363 (3) | N1—S1 | 1.6122 (19) |
C4—C5 | 1.410 (3) | N1—H1A | 0.9246 |
C5—C6 | 1.390 (3) | N1—H1B | 0.8990 |
C5—S2 | 1.750 (2) | N2—S2 | 1.6370 (19) |
C6—H6 | 0.9500 | N3—H3A | 0.8907 |
C7—N3 | 1.456 (3) | O1—S1 | 1.4293 (16) |
C7—N2 | 1.483 (3) | O2—S1 | 1.4394 (16) |
C7—C8 | 1.516 (3) | O3—S2 | 1.4305 (16) |
C7—H7 | 1.0000 | O4—S2 | 1.4346 (16) |
| | | |
C6—C1—C2 | 118.11 (18) | H8A—C8—H8B | 108.2 |
C6—C1—S1 | 117.40 (15) | N2—C9—H9A | 109.5 |
C2—C1—S1 | 124.49 (15) | N2—C9—H9B | 109.5 |
C3—C2—C1 | 122.23 (18) | H9A—C9—H9B | 109.5 |
C3—C2—Cl1 | 117.76 (15) | N2—C9—H9C | 109.5 |
C1—C2—Cl1 | 120.00 (15) | H9A—C9—H9C | 109.5 |
C2—C3—C4 | 120.24 (18) | H9B—C9—H9C | 109.5 |
C2—C3—H3 | 119.9 | S1—N1—H1A | 112.7 |
C4—C3—H3 | 119.9 | S1—N1—H1B | 115.2 |
N3—C4—C3 | 120.02 (18) | H1A—N1—H1B | 115.7 |
N3—C4—C5 | 122.65 (18) | C9—N2—C7 | 116.5 (2) |
C3—C4—C5 | 117.31 (18) | C9—N2—S2 | 114.87 (17) |
C6—C5—C4 | 121.67 (18) | C7—N2—S2 | 108.97 (14) |
C6—C5—S2 | 119.88 (15) | C4—N3—C7 | 121.56 (17) |
C4—C5—S2 | 118.40 (15) | C4—N3—H3A | 118.4 |
C1—C6—C5 | 120.40 (18) | C7—N3—H3A | 117.5 |
C1—C6—H6 | 119.8 | O1—S1—O2 | 118.52 (10) |
C5—C6—H6 | 119.8 | O1—S1—N1 | 107.58 (10) |
N3—C7—N2 | 109.75 (17) | O2—S1—N1 | 106.36 (10) |
N3—C7—C8 | 107.97 (18) | O1—S1—C1 | 106.20 (9) |
N2—C7—C8 | 112.3 (2) | O2—S1—C1 | 108.87 (9) |
N3—C7—H7 | 108.9 | N1—S1—C1 | 109.08 (10) |
N2—C7—H7 | 108.9 | O3—S2—O4 | 116.95 (10) |
C8—C7—H7 | 108.9 | O3—S2—N2 | 109.19 (10) |
C7—C8—Cl2 | 109.76 (17) | O4—S2—N2 | 107.91 (10) |
C7—C8—H8A | 109.7 | O3—S2—C5 | 110.03 (10) |
Cl2—C8—H8A | 109.7 | O4—S2—C5 | 109.72 (9) |
C7—C8—H8B | 109.7 | N2—S2—C5 | 101.97 (10) |
Cl2—C8—H8B | 109.7 | | |
Hydrogen-bond geometry (Å, º) top
D—H···A | D—H | H···A | D···A | D—H···A |
N1—H1A···O3i | 0.92 | 2.07 | 2.917 (2) | 152 |
N1—H1B···O4ii | 0.90 | 2.25 | 3.114 (2) | 162 |
N3—H3A···O2iii | 0.89 | 2.25 | 3.095 (2) | 158 |
Symmetry codes: (i) x−1/2, y, −z+1/2; (ii) x−1, y, z; (iii) −x+3/2, y−1/2, z. |