Buy article online - an online subscription or single-article purchase is required to access this article.
The title compound, C9H10ClN3O2S, was prepared for structural comparison with analogous products known as myorelaxants and inhibitors of insulin release. The 2H-tautomeric form is imposed by the presence of a methyl group in the 2-position. There are four independent molecules (A, B, C and D) in the asymmetric unit which have almost the same geometry. The C-N distances in the four thiadiazine rings [C-N single- and double-bond mean values of 1.405 (3) and 1.304 (3) Å, respectively] may serve as reference to characterize the 2H-tautomeric form in analogous structures. The NH group of the methylamino substituent of each molecule participates in an intermolecular hydrogen bond with a sulfoxide O atom acting as acceptor. These four independent hydrogen bonds give rise to two types of infinite chains, both stretching along the a axis and having molecular compositions of ...ABABAB... and ...CDCDCD...
Supporting information
CCDC reference: 170786
Key indicators
- Single-crystal X-ray study
- T = 293 K
- Mean (C-C) = 0.003 Å
- R factor = 0.036
- wR factor = 0.106
- Data-to-parameter ratio = 10.0
checkCIF results
No syntax errors found
ADDSYM reports no extra symmetry
Alert Level B:
THETM_01 Alert B The value of sine(theta_max)/wavelength is less than 0.575
Calculated sin(theta_max)/wavelength = 0.5566
Alert Level C:
REFLT_03
From the CIF: _diffrn_reflns_theta_max 23.30
From the CIF: _reflns_number_total 6008
TEST2: Reflns within _diffrn_reflns_theta_max
Count of symmetry unique reflns 6497
Completeness (_total/calc) 92.47%
Alert C: < 95% complete
0 Alert Level A = Potentially serious problem
1 Alert Level B = Potential problem
1 Alert Level C = Please check
A solution of
7-chloro-2-methyl-3-methylsulfanyl-2H-1,2,4-benzothiadiazine
1,1-dioxide [obtained as described in Di Bella et al. (1973)] (0.6 g)
in a 33% w/v solution of methylamine in methanol (15 ml) was
heated in a closed vessel at 373 K for 4 h. The excess solvent and amine were
removed by distillation under reduced pressure and the resulting residue was
suspended in distilled water (40 ml) and stirred for 15 min. The insoluble
material (final compound) was collected by filtration, washed with water and
recrystallized from the methanol–water (1:2) mixture (yield: 60%; m.p.
456–457 K)..
The diffraction data are limited because of a rather poor quality of the
crystal. The data collection was stopped when the Rint of the
equivalent reflections became too high. All H atoms [with the exception of the
nitrogen-bound atoms H11(A—D)] were included in the refinement in the riding
model approximation with isotropic displacement parameters fixed at
1.2Ueq of the parent atom (1.5Ueq for methyl H atoms). The
H11(A—D) atoms were refined isotropically (their displacement parameters
being fixed at 1.2Ueq of the corresponding nitogen atom). The N—H
distances are in the range 0.78–0.86 Å. Even though their geometrical
similarity and peculiar relative disposition suggest that the
crystallographically independent molecules are pairwise related by the local
symmetry elements, the thorough check for additional genuine crystal symmetry
yielded no result.
Data collection: MAR software; cell refinement: marHKL software; data reduction: marHKL software; 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.
7-chloro-2-methyl-3-methylamino-2
H-1,2,4-benzothiadiazine 1,1-dioxide
top
Crystal data top
C9H10ClN3O2S | F(000) = 2144 |
Mr = 259.71 | Dx = 1.534 Mg m−3 |
Monoclinic, P21/a | Mo Kα radiation, λ = 0.71069 Å |
a = 10.096 (1) Å | Cell parameters from 219 reflections |
b = 26.316 (2) Å | θ = 2.6–23.3° |
c = 16.927 (2) Å | µ = 0.51 mm−1 |
β = 90.070 (2)° | T = 293 K |
V = 4497.3 (8) Å3 | Prism, colourless |
Z = 16 | 0.30 × 0.30 × 0.30 mm |
Data collection top
MAR345 image-plate diffractometer | 4970 reflections with I > 2σ(I) |
Radiation source: RU200 rotating anode | Rint = 0.039 |
Graphite monochromator | θmax = 23.3°, θmin = 2.6° |
Detector resolution: 6.66 pixels mm-1 | h = 0→10 |
119 images, 130 mm, ΔΦ 3° scans | k = 0→29 |
38152 measured reflections | l = −18→18 |
6008 independent reflections | |
Refinement top
Refinement on F2 | Secondary atom site location: difference Fourier map |
Least-squares matrix: full | Hydrogen site location: H atoms were placed at standard calculated positions, except atoms H(N11)
which were obtained from difference map. |
R[F2 > 2σ(F2)] = 0.036 | H atoms treated by a mixture of independent and constrained refinement |
wR(F2) = 0.106 | w = 1/[σ2(Fo2) + (0.064P)2 + 0.5031P] where P = (Fo2 + 2Fc2)/3 |
S = 1.07 | (Δ/σ)max = 0.002 |
6008 reflections | Δρmax = 0.25 e Å−3 |
598 parameters | Δρmin = −0.27 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: 0.0065 (4) |
Crystal data top
C9H10ClN3O2S | V = 4497.3 (8) Å3 |
Mr = 259.71 | Z = 16 |
Monoclinic, P21/a | Mo Kα radiation |
a = 10.096 (1) Å | µ = 0.51 mm−1 |
b = 26.316 (2) Å | T = 293 K |
c = 16.927 (2) Å | 0.30 × 0.30 × 0.30 mm |
β = 90.070 (2)° | |
Data collection top
MAR345 image-plate diffractometer | 4970 reflections with I > 2σ(I) |
38152 measured reflections | Rint = 0.039 |
6008 independent reflections | θmax = 23.3° |
Refinement top
R[F2 > 2σ(F2)] = 0.036 | 0 restraints |
wR(F2) = 0.106 | H atoms treated by a mixture of independent and constrained refinement |
S = 1.07 | Δρmax = 0.25 e Å−3 |
6008 reflections | Δρmin = −0.27 e Å−3 |
598 parameters | |
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 | |
S1A | 0.73080 (5) | 0.313750 (19) | 0.06113 (3) | 0.03802 (17) | |
O1A | 0.65228 (15) | 0.31544 (6) | −0.00935 (10) | 0.0526 (4) | |
O2A | 0.73479 (16) | 0.26694 (5) | 0.10321 (10) | 0.0531 (4) | |
N2A | 0.88417 (16) | 0.33030 (6) | 0.04059 (11) | 0.0387 (4) | |
C3A | 0.9039 (2) | 0.38088 (7) | 0.01607 (13) | 0.0347 (5) | |
N4A | 0.83590 (17) | 0.41918 (6) | 0.04278 (11) | 0.0385 (4) | |
C5A | 0.7424 (2) | 0.41131 (7) | 0.10169 (13) | 0.0355 (5) | |
C6A | 0.6964 (2) | 0.45310 (8) | 0.14525 (14) | 0.0431 (6) | |
H6A | 0.7285 | 0.4854 | 0.1337 | 0.052* | |
C7A | 0.6051 (2) | 0.44725 (8) | 0.20447 (14) | 0.0458 (6) | |
H7A | 0.5758 | 0.4755 | 0.2323 | 0.055* | |
C8A | 0.5559 (2) | 0.39952 (9) | 0.22323 (13) | 0.0431 (6) | |
C9A | 0.5951 (2) | 0.35730 (8) | 0.18139 (13) | 0.0428 (5) | |
H9A | 0.5610 | 0.3253 | 0.1928 | 0.051* | |
C10A | 0.6877 (2) | 0.36406 (7) | 0.12133 (13) | 0.0358 (5) | |
N11A | 1.00236 (18) | 0.38852 (7) | −0.03531 (12) | 0.0422 (5) | |
H11A | 1.034 (2) | 0.3641 (9) | −0.0535 (14) | 0.051* | |
C12A | 1.0459 (2) | 0.43882 (9) | −0.05774 (14) | 0.0501 (6) | |
H121 | 0.9754 | 0.4561 | −0.0847 | 0.075* | |
H122 | 1.1211 | 0.4361 | −0.0922 | 0.075* | |
H123 | 1.0702 | 0.4576 | −0.0113 | 0.075* | |
C13A | 0.9800 (2) | 0.28951 (9) | 0.02487 (17) | 0.0631 (7) | |
H131 | 0.9690 | 0.2776 | −0.0283 | 0.095* | |
H132 | 0.9654 | 0.2620 | 0.0610 | 0.095* | |
H133 | 1.0684 | 0.3023 | 0.0316 | 0.095* | |
Cl1A | 0.44215 (6) | 0.39293 (3) | 0.29959 (4) | 0.0644 (2) | |
S1B | −0.23939 (5) | 0.689769 (19) | 0.20463 (4) | 0.03986 (18) | |
O1B | −0.16326 (15) | 0.68925 (6) | 0.13292 (10) | 0.0525 (4) | |
O2B | −0.25017 (15) | 0.73676 (5) | 0.24575 (10) | 0.0550 (4) | |
N2B | −0.39074 (16) | 0.66897 (6) | 0.18613 (11) | 0.0392 (4) | |
C3B | −0.4006 (2) | 0.61801 (7) | 0.16201 (13) | 0.0344 (5) | |
N4B | −0.32518 (17) | 0.58175 (6) | 0.18860 (11) | 0.0377 (4) | |
C5B | −0.2314 (2) | 0.59229 (7) | 0.24640 (13) | 0.0360 (5) | |
C6B | −0.1741 (2) | 0.55231 (8) | 0.28929 (13) | 0.0431 (6) | |
H6B | −0.1982 | 0.5191 | 0.2775 | 0.052* | |
C7B | −0.0836 (2) | 0.56106 (9) | 0.34807 (14) | 0.0481 (6) | |
H7B | −0.0475 | 0.5338 | 0.3756 | 0.058* | |
C8B | −0.0454 (2) | 0.61018 (9) | 0.36680 (14) | 0.0469 (6) | |
C9B | −0.0943 (2) | 0.65075 (9) | 0.32491 (13) | 0.0445 (6) | |
H9B | −0.0672 | 0.6837 | 0.3363 | 0.053* | |
C10B | −0.1854 (2) | 0.64117 (8) | 0.26504 (13) | 0.0373 (5) | |
N11B | −0.49807 (19) | 0.60782 (7) | 0.11092 (12) | 0.0432 (5) | |
H11B | −0.534 (2) | 0.6322 (9) | 0.0900 (15) | 0.052* | |
C12B | −0.5316 (2) | 0.55651 (9) | 0.08651 (15) | 0.0525 (6) | |
H124 | −0.4598 | 0.5424 | 0.0565 | 0.079* | |
H125 | −0.6102 | 0.5573 | 0.0545 | 0.079* | |
H126 | −0.5471 | 0.5359 | 0.1324 | 0.079* | |
C13B | −0.4944 (2) | 0.70673 (8) | 0.17262 (16) | 0.0553 (7) | |
H134 | −0.4888 | 0.7190 | 0.1193 | 0.083* | |
H135 | −0.4830 | 0.7345 | 0.2087 | 0.083* | |
H136 | −0.5796 | 0.6914 | 0.1809 | 0.083* | |
Cl1B | 0.06561 (6) | 0.62083 (3) | 0.44353 (4) | 0.0696 (2) | |
S1C | 0.47269 (5) | 0.683672 (19) | 0.43689 (3) | 0.03947 (18) | |
O1C | 0.39406 (16) | 0.68284 (6) | 0.50731 (10) | 0.0529 (4) | |
O2C | 0.47578 (16) | 0.72969 (6) | 0.39342 (10) | 0.0565 (5) | |
N2C | 0.62665 (17) | 0.66763 (6) | 0.45840 (11) | 0.0402 (4) | |
C3C | 0.6481 (2) | 0.61749 (7) | 0.48337 (13) | 0.0361 (5) | |
N4C | 0.58043 (17) | 0.57849 (6) | 0.45763 (11) | 0.0402 (4) | |
C5C | 0.4858 (2) | 0.58533 (8) | 0.39925 (13) | 0.0376 (5) | |
C6C | 0.4384 (2) | 0.54298 (8) | 0.35812 (14) | 0.0457 (6) | |
H6C | 0.4698 | 0.5108 | 0.3712 | 0.055* | |
C7C | 0.3459 (2) | 0.54785 (9) | 0.29853 (14) | 0.0508 (6) | |
H7C | 0.3158 | 0.5191 | 0.2720 | 0.061* | |
C8C | 0.2977 (2) | 0.59518 (9) | 0.27803 (14) | 0.0469 (6) | |
C9C | 0.3371 (2) | 0.63789 (9) | 0.31803 (14) | 0.0461 (6) | |
H9C | 0.3028 | 0.6697 | 0.3054 | 0.055* | |
C10C | 0.4303 (2) | 0.63221 (8) | 0.37840 (13) | 0.0382 (5) | |
N11C | 0.74755 (18) | 0.61037 (7) | 0.53443 (12) | 0.0442 (5) | |
H11C | 0.779 (2) | 0.6373 (9) | 0.5527 (14) | 0.053* | |
C12C | 0.7926 (2) | 0.56032 (9) | 0.55669 (15) | 0.0524 (6) | |
H127 | 0.7253 | 0.5437 | 0.5872 | 0.079* | |
H128 | 0.8720 | 0.5632 | 0.5877 | 0.079* | |
H129 | 0.8106 | 0.5408 | 0.5100 | 0.079* | |
C13C | 0.7195 (2) | 0.70916 (9) | 0.47544 (17) | 0.0600 (7) | |
H137 | 0.7075 | 0.7204 | 0.5289 | 0.090* | |
H138 | 0.7029 | 0.7369 | 0.4400 | 0.090* | |
H139 | 0.8086 | 0.6973 | 0.4685 | 0.090* | |
Cl1C | 0.18374 (7) | 0.60094 (3) | 0.20151 (4) | 0.0697 (2) | |
S1D | 0.02320 (5) | 0.313087 (19) | 0.29261 (3) | 0.04001 (18) | |
O1D | 0.10049 (15) | 0.31330 (6) | 0.36374 (10) | 0.0527 (4) | |
O2D | 0.01531 (16) | 0.26663 (5) | 0.25003 (10) | 0.0554 (5) | |
N2D | −0.12931 (16) | 0.33185 (6) | 0.31213 (10) | 0.0388 (4) | |
C3D | −0.1436 (2) | 0.38230 (7) | 0.33810 (13) | 0.0342 (5) | |
N4D | −0.07141 (16) | 0.41999 (6) | 0.31175 (11) | 0.0381 (4) | |
C5D | 0.0215 (2) | 0.41125 (7) | 0.25310 (13) | 0.0365 (5) | |
C6D | 0.0729 (2) | 0.45212 (8) | 0.20993 (14) | 0.0463 (6) | |
H6D | 0.0442 | 0.4849 | 0.2215 | 0.056* | |
C7D | 0.1645 (2) | 0.44526 (9) | 0.15092 (14) | 0.0510 (6) | |
H7D | 0.1968 | 0.4732 | 0.1233 | 0.061* | |
C8D | 0.2089 (2) | 0.39695 (10) | 0.13245 (14) | 0.0492 (6) | |
C9D | 0.1646 (2) | 0.35526 (9) | 0.17372 (14) | 0.0468 (6) | |
H9D | 0.1955 | 0.3228 | 0.1622 | 0.056* | |
C10D | 0.0723 (2) | 0.36322 (8) | 0.23319 (13) | 0.0397 (5) | |
N11D | −0.23932 (18) | 0.39073 (7) | 0.39063 (12) | 0.0419 (5) | |
H11D | −0.278 (2) | 0.3649 (9) | 0.4113 (14) | 0.050* | |
C12D | −0.2739 (2) | 0.44116 (9) | 0.41822 (15) | 0.0536 (6) | |
H12A | −0.1998 | 0.4557 | 0.4457 | 0.080* | |
H12B | −0.3483 | 0.4390 | 0.4534 | 0.080* | |
H12C | −0.2966 | 0.4622 | 0.3739 | 0.080* | |
C13D | −0.2284 (2) | 0.29255 (8) | 0.32816 (16) | 0.0569 (7) | |
H13A | −0.2197 | 0.2812 | 0.3818 | 0.085* | |
H13B | −0.2149 | 0.2644 | 0.2931 | 0.085* | |
H13C | −0.3154 | 0.3063 | 0.3201 | 0.085* | |
Cl1D | 0.32229 (7) | 0.38835 (3) | 0.05652 (4) | 0.0739 (2) | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
S1A | 0.0420 (3) | 0.0297 (3) | 0.0424 (4) | −0.0012 (2) | −0.0026 (3) | −0.0017 (2) |
O1A | 0.0566 (10) | 0.0529 (10) | 0.0483 (11) | −0.0019 (7) | −0.0146 (8) | −0.0101 (7) |
O2A | 0.0619 (10) | 0.0308 (9) | 0.0667 (12) | −0.0022 (7) | 0.0035 (8) | 0.0065 (7) |
N2A | 0.0387 (10) | 0.0297 (9) | 0.0478 (12) | 0.0058 (7) | 0.0032 (8) | −0.0001 (8) |
C3A | 0.0390 (12) | 0.0321 (12) | 0.0331 (14) | 0.0012 (9) | −0.0041 (9) | −0.0011 (9) |
N4A | 0.0417 (10) | 0.0339 (10) | 0.0399 (12) | 0.0022 (8) | 0.0046 (8) | −0.0001 (8) |
C5A | 0.0377 (12) | 0.0337 (12) | 0.0351 (14) | 0.0031 (9) | −0.0026 (10) | 0.0004 (9) |
C6A | 0.0480 (13) | 0.0340 (12) | 0.0474 (16) | 0.0043 (9) | 0.0022 (11) | −0.0033 (10) |
C7A | 0.0489 (14) | 0.0467 (14) | 0.0419 (16) | 0.0080 (10) | 0.0002 (11) | −0.0097 (11) |
C8A | 0.0382 (13) | 0.0562 (15) | 0.0350 (15) | 0.0036 (10) | 0.0018 (10) | −0.0036 (11) |
C9A | 0.0408 (13) | 0.0471 (14) | 0.0405 (15) | −0.0049 (10) | −0.0026 (10) | 0.0043 (11) |
C10A | 0.0367 (12) | 0.0360 (12) | 0.0347 (14) | 0.0026 (9) | −0.0017 (9) | 0.0008 (9) |
N11A | 0.0462 (11) | 0.0372 (11) | 0.0432 (13) | 0.0017 (8) | 0.0095 (9) | −0.0033 (9) |
C12A | 0.0561 (15) | 0.0465 (14) | 0.0477 (17) | −0.0045 (11) | 0.0086 (12) | 0.0032 (11) |
C13A | 0.0641 (16) | 0.0413 (14) | 0.084 (2) | 0.0182 (12) | 0.0193 (14) | 0.0006 (13) |
Cl1A | 0.0530 (4) | 0.0894 (5) | 0.0510 (5) | −0.0038 (3) | 0.0163 (3) | −0.0065 (3) |
S1B | 0.0430 (3) | 0.0296 (3) | 0.0471 (4) | −0.0022 (2) | 0.0059 (3) | −0.0009 (2) |
O1B | 0.0577 (10) | 0.0488 (10) | 0.0510 (11) | −0.0034 (7) | 0.0157 (8) | 0.0076 (7) |
O2B | 0.0624 (10) | 0.0323 (9) | 0.0705 (13) | −0.0019 (7) | 0.0017 (9) | −0.0101 (8) |
N2B | 0.0382 (10) | 0.0312 (10) | 0.0482 (12) | 0.0043 (7) | 0.0008 (8) | −0.0015 (8) |
C3B | 0.0363 (12) | 0.0322 (12) | 0.0347 (14) | −0.0017 (9) | 0.0047 (10) | 0.0010 (9) |
N4B | 0.0419 (10) | 0.0311 (10) | 0.0399 (12) | 0.0008 (8) | −0.0006 (8) | −0.0009 (8) |
C5B | 0.0382 (12) | 0.0342 (12) | 0.0358 (14) | 0.0003 (9) | 0.0051 (10) | −0.0026 (9) |
C6B | 0.0499 (14) | 0.0371 (13) | 0.0424 (16) | 0.0022 (10) | 0.0018 (11) | 0.0045 (10) |
C7B | 0.0473 (14) | 0.0547 (15) | 0.0424 (16) | 0.0052 (11) | −0.0006 (11) | 0.0087 (11) |
C8B | 0.0408 (13) | 0.0618 (16) | 0.0380 (16) | 0.0001 (11) | −0.0002 (10) | −0.0021 (11) |
C9B | 0.0441 (13) | 0.0474 (14) | 0.0421 (15) | −0.0062 (10) | 0.0033 (10) | −0.0087 (11) |
C10B | 0.0367 (12) | 0.0364 (12) | 0.0388 (14) | 0.0007 (9) | 0.0048 (10) | −0.0036 (9) |
N11B | 0.0461 (11) | 0.0390 (12) | 0.0445 (14) | 0.0013 (8) | −0.0051 (9) | 0.0035 (9) |
C12B | 0.0590 (15) | 0.0454 (14) | 0.0529 (17) | −0.0097 (11) | −0.0096 (12) | −0.0033 (11) |
C13B | 0.0596 (15) | 0.0428 (14) | 0.0635 (18) | 0.0174 (11) | −0.0120 (12) | −0.0001 (12) |
Cl1B | 0.0540 (4) | 0.1031 (6) | 0.0516 (5) | −0.0078 (3) | −0.0142 (3) | −0.0016 (4) |
S1C | 0.0420 (3) | 0.0340 (3) | 0.0424 (4) | 0.0011 (2) | 0.0040 (3) | −0.0003 (2) |
O1C | 0.0566 (10) | 0.0547 (10) | 0.0475 (11) | 0.0024 (7) | 0.0154 (8) | −0.0085 (8) |
O2C | 0.0656 (11) | 0.0366 (9) | 0.0673 (13) | 0.0019 (7) | −0.0024 (9) | 0.0107 (8) |
N2C | 0.0401 (10) | 0.0337 (10) | 0.0467 (12) | −0.0066 (8) | 0.0003 (8) | −0.0008 (8) |
C3C | 0.0389 (12) | 0.0343 (12) | 0.0353 (14) | −0.0004 (9) | 0.0032 (10) | −0.0010 (9) |
N4C | 0.0419 (10) | 0.0372 (10) | 0.0415 (12) | −0.0030 (8) | −0.0019 (8) | −0.0017 (8) |
C5C | 0.0378 (12) | 0.0387 (13) | 0.0363 (14) | −0.0031 (9) | 0.0033 (10) | −0.0009 (10) |
C6C | 0.0485 (14) | 0.0397 (13) | 0.0489 (16) | −0.0050 (10) | −0.0008 (11) | −0.0075 (11) |
C7C | 0.0478 (14) | 0.0570 (16) | 0.0476 (17) | −0.0099 (11) | 0.0016 (11) | −0.0127 (12) |
C8C | 0.0381 (13) | 0.0659 (17) | 0.0365 (16) | −0.0060 (11) | −0.0012 (10) | −0.0050 (11) |
C9C | 0.0418 (13) | 0.0550 (15) | 0.0414 (16) | 0.0027 (10) | 0.0032 (11) | 0.0059 (11) |
C10C | 0.0374 (12) | 0.0420 (13) | 0.0351 (14) | −0.0035 (9) | 0.0046 (9) | 0.0001 (10) |
N11C | 0.0479 (12) | 0.0416 (12) | 0.0433 (13) | −0.0038 (8) | −0.0072 (9) | −0.0034 (9) |
C12C | 0.0536 (15) | 0.0522 (15) | 0.0514 (17) | 0.0070 (11) | −0.0077 (12) | 0.0033 (12) |
C13C | 0.0605 (16) | 0.0434 (14) | 0.076 (2) | −0.0160 (11) | −0.0121 (13) | −0.0044 (13) |
Cl1C | 0.0532 (4) | 0.1048 (6) | 0.0509 (5) | −0.0024 (3) | −0.0146 (3) | −0.0059 (4) |
S1D | 0.0425 (3) | 0.0327 (3) | 0.0448 (4) | 0.0039 (2) | −0.0041 (3) | −0.0021 (2) |
O1D | 0.0567 (10) | 0.0512 (10) | 0.0502 (11) | 0.0064 (7) | −0.0162 (8) | 0.0047 (8) |
O2D | 0.0653 (11) | 0.0342 (9) | 0.0666 (12) | 0.0046 (7) | 0.0006 (9) | −0.0134 (8) |
N2D | 0.0398 (10) | 0.0316 (10) | 0.0451 (12) | −0.0035 (7) | 0.0006 (8) | −0.0007 (8) |
C3D | 0.0369 (12) | 0.0323 (12) | 0.0335 (14) | 0.0019 (9) | −0.0030 (9) | 0.0024 (9) |
N4D | 0.0420 (10) | 0.0338 (10) | 0.0385 (12) | 0.0001 (8) | 0.0027 (8) | 0.0008 (8) |
C5D | 0.0371 (12) | 0.0367 (12) | 0.0358 (14) | −0.0022 (9) | −0.0022 (10) | −0.0024 (9) |
C6D | 0.0481 (14) | 0.0419 (13) | 0.0489 (16) | −0.0032 (10) | 0.0026 (11) | 0.0049 (11) |
C7D | 0.0458 (14) | 0.0604 (16) | 0.0468 (17) | −0.0080 (11) | 0.0010 (11) | 0.0081 (12) |
C8D | 0.0386 (13) | 0.0694 (17) | 0.0396 (16) | −0.0003 (11) | 0.0008 (11) | 0.0004 (12) |
C9D | 0.0402 (13) | 0.0558 (15) | 0.0444 (16) | 0.0078 (10) | −0.0023 (11) | −0.0085 (12) |
C10D | 0.0364 (12) | 0.0434 (13) | 0.0392 (15) | −0.0003 (9) | −0.0050 (10) | −0.0048 (10) |
N11D | 0.0461 (11) | 0.0382 (11) | 0.0415 (13) | −0.0001 (8) | 0.0066 (9) | 0.0034 (9) |
C12D | 0.0611 (15) | 0.0469 (15) | 0.0528 (17) | 0.0111 (11) | 0.0125 (12) | 0.0008 (11) |
C13D | 0.0609 (15) | 0.0406 (14) | 0.0694 (19) | −0.0151 (11) | 0.0104 (13) | 0.0031 (12) |
Cl1D | 0.0531 (4) | 0.1160 (6) | 0.0526 (5) | 0.0097 (4) | 0.0169 (3) | 0.0048 (4) |
Geometric parameters (Å, º) top
S1A—O1A | 1.4322 (16) | S1C—O1C | 1.4332 (16) |
S1A—O2A | 1.4235 (16) | S1C—O2C | 1.4173 (16) |
S1A—N2A | 1.6461 (18) | S1C—N2C | 1.6509 (18) |
S1A—C10A | 1.727 (2) | S1C—C10C | 1.731 (2) |
N2A—C3A | 1.408 (3) | N2C—C3C | 1.402 (3) |
N2A—C13A | 1.470 (3) | N2C—C13C | 1.468 (3) |
C3A—N4A | 1.301 (3) | C3C—N4C | 1.307 (3) |
C3A—N11A | 1.337 (3) | C3C—N11C | 1.337 (3) |
N4A—C5A | 1.390 (3) | N4C—C5C | 1.386 (3) |
C5A—C10A | 1.401 (3) | C5C—C6C | 1.398 (3) |
C5A—C6A | 1.403 (3) | C5C—C10C | 1.400 (3) |
C6A—C7A | 1.371 (3) | C6C—C7C | 1.379 (3) |
C6A—H6A | 0.9300 | C6C—H6C | 0.9300 |
C7A—C8A | 1.387 (3) | C7C—C8C | 1.381 (3) |
C7A—H7A | 0.9300 | C7C—H7C | 0.9300 |
C8A—C9A | 1.376 (3) | C8C—C9C | 1.371 (3) |
C8A—Cl1A | 1.739 (2) | C8C—Cl1C | 1.738 (2) |
C9A—C10A | 1.393 (3) | C9C—C10C | 1.396 (3) |
C9A—H9A | 0.9300 | C9C—H9C | 0.9300 |
N11A—C12A | 1.446 (3) | N11C—C12C | 1.444 (3) |
N11A—H11A | 0.78 (2) | N11C—H11C | 0.84 (2) |
C12A—H121 | 0.9600 | C12C—H127 | 0.9600 |
C12A—H122 | 0.9600 | C12C—H128 | 0.9600 |
C12A—H123 | 0.9600 | C12C—H129 | 0.9600 |
C13A—H131 | 0.9600 | C13C—H137 | 0.9600 |
C13A—H132 | 0.9600 | C13C—H138 | 0.9600 |
C13A—H133 | 0.9600 | C13C—H139 | 0.9600 |
S1B—O1B | 1.4376 (16) | S1D—O1D | 1.4340 (16) |
S1B—O2B | 1.4233 (15) | S1D—O2D | 1.4214 (15) |
S1B—N2B | 1.6526 (17) | S1D—N2D | 1.6508 (17) |
S1B—C10B | 1.725 (2) | S1D—C10D | 1.732 (2) |
N2B—C3B | 1.405 (2) | N2D—C3D | 1.406 (3) |
N2B—C13B | 1.461 (3) | N2D—C13D | 1.464 (3) |
C3B—N4B | 1.301 (3) | C3D—N4D | 1.309 (3) |
C3B—N11B | 1.336 (3) | C3D—N11D | 1.333 (3) |
N4B—C5B | 1.389 (3) | N4D—C5D | 1.386 (3) |
C5B—C6B | 1.402 (3) | C5D—C6D | 1.401 (3) |
C5B—C10B | 1.403 (3) | C5D—C10D | 1.405 (3) |
C6B—C7B | 1.370 (3) | C6D—C7D | 1.374 (3) |
C6B—H6B | 0.9300 | C6D—H6D | 0.9300 |
C7B—C8B | 1.386 (3) | C7D—C8D | 1.384 (3) |
C7B—H7B | 0.9300 | C7D—H7D | 0.9300 |
C8B—C9B | 1.373 (3) | C8D—C9D | 1.376 (3) |
C8B—Cl1B | 1.737 (2) | C8D—Cl1D | 1.737 (2) |
C9B—C10B | 1.391 (3) | C9D—C10D | 1.389 (3) |
C9B—H9B | 0.9300 | C9D—H9D | 0.9300 |
N11B—C12B | 1.452 (3) | N11D—C12D | 1.450 (3) |
N11B—H11B | 0.82 (2) | N11D—H11D | 0.86 (2) |
C12B—H124 | 0.9600 | C12D—H12A | 0.9600 |
C12B—H125 | 0.9600 | C12D—H12B | 0.9600 |
C12B—H126 | 0.9600 | C12D—H12C | 0.9600 |
C13B—H134 | 0.9600 | C13D—H13A | 0.9600 |
C13B—H135 | 0.9600 | C13D—H13B | 0.9600 |
C13B—H136 | 0.9600 | C13D—H13C | 0.9600 |
| | | |
O2A—S1A—O1A | 117.32 (9) | O2C—S1C—O1C | 117.22 (10) |
O2A—S1A—N2A | 107.97 (9) | O2C—S1C—N2C | 108.16 (9) |
O1A—S1A—N2A | 109.62 (10) | O1C—S1C—N2C | 109.57 (10) |
O2A—S1A—C10A | 112.03 (10) | O2C—S1C—C10C | 112.15 (11) |
O1A—S1A—C10A | 109.14 (9) | O1C—S1C—C10C | 109.09 (10) |
N2A—S1A—C10A | 99.20 (9) | N2C—S1C—C10C | 99.09 (9) |
C3A—N2A—C13A | 122.90 (18) | C3C—N2C—C13C | 122.90 (18) |
C3A—N2A—S1A | 116.48 (13) | C3C—N2C—S1C | 116.88 (13) |
C13A—N2A—S1A | 117.70 (15) | C13C—N2C—S1C | 116.96 (15) |
N4A—C3A—N11A | 120.17 (19) | N4C—C3C—N11C | 119.81 (19) |
N4A—C3A—N2A | 123.69 (19) | N4C—C3C—N2C | 123.91 (19) |
N11A—C3A—N2A | 116.09 (17) | N11C—C3C—N2C | 116.24 (18) |
C3A—N4A—C5A | 119.55 (17) | C3C—N4C—C5C | 119.69 (18) |
N4A—C5A—C10A | 124.83 (18) | N4C—C5C—C6C | 119.14 (19) |
N4A—C5A—C6A | 119.05 (18) | N4C—C5C—C10C | 124.73 (19) |
C10A—C5A—C6A | 116.1 (2) | C6C—C5C—C10C | 116.1 (2) |
C7A—C6A—C5A | 121.3 (2) | C7C—C6C—C5C | 121.4 (2) |
C7A—C6A—H6A | 119.4 | C7C—C6C—H6C | 119.3 |
C5A—C6A—H6A | 119.4 | C5C—C6C—H6C | 119.3 |
C6A—C7A—C8A | 120.7 (2) | C6C—C7C—C8C | 120.4 (2) |
C6A—C7A—H7A | 119.7 | C6C—C7C—H7C | 119.8 |
C8A—C7A—H7A | 119.7 | C8C—C7C—H7C | 119.8 |
C9A—C8A—C7A | 120.7 (2) | C9C—C8C—C7C | 120.9 (2) |
C9A—C8A—Cl1A | 119.52 (18) | C9C—C8C—Cl1C | 119.19 (19) |
C7A—C8A—Cl1A | 119.82 (17) | C7C—C8C—Cl1C | 119.90 (18) |
C8A—C9A—C10A | 117.8 (2) | C8C—C9C—C10C | 117.9 (2) |
C8A—C9A—H9A | 121.1 | C8C—C9C—H9C | 121.0 |
C10A—C9A—H9A | 121.1 | C10C—C9C—H9C | 121.0 |
C9A—C10A—C5A | 123.47 (19) | C9C—C10C—C5C | 123.2 (2) |
C9A—C10A—S1A | 120.18 (16) | C9C—C10C—S1C | 120.04 (17) |
C5A—C10A—S1A | 116.14 (16) | C5C—C10C—S1C | 116.53 (16) |
C3A—N11A—C12A | 122.37 (19) | C3C—N11C—C12C | 122.19 (19) |
C3A—N11A—H11A | 116.0 (19) | C3C—N11C—H11C | 114.0 (17) |
C12A—N11A—H11A | 121.7 (19) | C12C—N11C—H11C | 123.8 (17) |
N11A—C12A—H121 | 109.5 | N11C—C12C—H127 | 109.5 |
N11A—C12A—H122 | 109.5 | N11C—C12C—H128 | 109.5 |
H121—C12A—H122 | 109.5 | H127—C12C—H128 | 109.5 |
N11A—C12A—H123 | 109.5 | N11C—C12C—H129 | 109.5 |
H121—C12A—H123 | 109.5 | H127—C12C—H129 | 109.5 |
H122—C12A—H123 | 109.5 | H128—C12C—H129 | 109.5 |
N2A—C13A—H131 | 109.5 | N2C—C13C—H137 | 109.5 |
N2A—C13A—H132 | 109.5 | N2C—C13C—H138 | 109.5 |
H131—C13A—H132 | 109.5 | H137—C13C—H138 | 109.5 |
N2A—C13A—H133 | 109.5 | N2C—C13C—H139 | 109.5 |
H131—C13A—H133 | 109.5 | H137—C13C—H139 | 109.5 |
H132—C13A—H133 | 109.5 | H138—C13C—H139 | 109.5 |
O2B—S1B—O1B | 117.54 (9) | O2D—S1D—O1D | 117.34 (9) |
O2B—S1B—N2B | 108.01 (9) | O2D—S1D—N2D | 107.88 (9) |
O1B—S1B—N2B | 109.38 (10) | O1D—S1D—N2D | 109.73 (10) |
O2B—S1B—C10B | 112.24 (10) | O2D—S1D—C10D | 112.13 (11) |
O1B—S1B—C10B | 108.94 (10) | O1D—S1D—C10D | 109.20 (10) |
N2B—S1B—C10B | 99.10 (9) | N2D—S1D—C10D | 98.97 (9) |
C3B—N2B—C13B | 123.56 (17) | C3D—N2D—C13D | 122.58 (17) |
C3B—N2B—S1B | 115.87 (13) | C3D—N2D—S1D | 116.17 (13) |
C13B—N2B—S1B | 117.82 (14) | C13D—N2D—S1D | 117.60 (14) |
N4B—C3B—N11B | 120.46 (19) | N4D—C3D—N11D | 120.38 (19) |
N4B—C3B—N2B | 123.93 (19) | N4D—C3D—N2D | 123.45 (19) |
N11B—C3B—N2B | 115.56 (18) | N11D—C3D—N2D | 116.14 (18) |
C3B—N4B—C5B | 119.71 (17) | C3D—N4D—C5D | 119.73 (17) |
N4B—C5B—C6B | 119.68 (18) | N4D—C5D—C6D | 119.88 (19) |
N4B—C5B—C10B | 124.51 (19) | N4D—C5D—C10D | 124.64 (19) |
C6B—C5B—C10B | 115.8 (2) | C6D—C5D—C10D | 115.5 (2) |
C7B—C6B—C5B | 121.6 (2) | C7D—C6D—C5D | 121.9 (2) |
C7B—C6B—H6B | 119.2 | C7D—C6D—H6D | 119.0 |
C5B—C6B—H6B | 119.2 | C5D—C6D—H6D | 119.0 |
C6B—C7B—C8B | 120.6 (2) | C6D—C7D—C8D | 120.2 (2) |
C6B—C7B—H7B | 119.7 | C6D—C7D—H7D | 119.9 |
C8B—C7B—H7B | 119.7 | C8D—C7D—H7D | 119.9 |
C9B—C8B—C7B | 120.5 (2) | C9D—C8D—C7D | 120.8 (2) |
C9B—C8B—Cl1B | 119.46 (18) | C9D—C8D—Cl1D | 119.12 (19) |
C7B—C8B—Cl1B | 120.06 (18) | C7D—C8D—Cl1D | 120.04 (19) |
C8B—C9B—C10B | 118.2 (2) | C8D—C9D—C10D | 117.8 (2) |
C8B—C9B—H9B | 120.9 | C8D—C9D—H9D | 121.1 |
C10B—C9B—H9B | 120.9 | C10D—C9D—H9D | 121.1 |
C9B—C10B—C5B | 123.2 (2) | C9D—C10D—C5D | 123.7 (2) |
C9B—C10B—S1B | 120.37 (16) | C9D—C10D—S1D | 119.93 (17) |
C5B—C10B—S1B | 116.24 (17) | C5D—C10D—S1D | 116.19 (17) |
C3B—N11B—C12B | 122.83 (19) | C3D—N11D—C12D | 122.86 (19) |
C3B—N11B—H11B | 116.9 (17) | C3D—N11D—H11D | 118.1 (16) |
C12B—N11B—H11B | 120.0 (17) | C12D—N11D—H11D | 118.9 (16) |
N11B—C12B—H124 | 109.5 | N11D—C12D—H12A | 109.5 |
N11B—C12B—H125 | 109.5 | N11D—C12D—H12B | 109.5 |
H124—C12B—H125 | 109.5 | H12A—C12D—H12B | 109.5 |
N11B—C12B—H126 | 109.5 | N11D—C12D—H12C | 109.5 |
H124—C12B—H126 | 109.5 | H12A—C12D—H12C | 109.5 |
H125—C12B—H126 | 109.5 | H12B—C12D—H12C | 109.5 |
N2B—C13B—H134 | 109.5 | N2D—C13D—H13A | 109.5 |
N2B—C13B—H135 | 109.5 | N2D—C13D—H13B | 109.5 |
H134—C13B—H135 | 109.5 | H13A—C13D—H13B | 109.5 |
N2B—C13B—H136 | 109.5 | N2D—C13D—H13C | 109.5 |
H134—C13B—H136 | 109.5 | H13A—C13D—H13C | 109.5 |
H135—C13B—H136 | 109.5 | H13B—C13D—H13C | 109.5 |
| | | |
O2A—S1A—N2A—C3A | −165.34 (15) | O2C—S1C—N2C—C3C | −164.34 (16) |
O1A—S1A—N2A—C3A | 65.76 (17) | O1C—S1C—N2C—C3C | 66.80 (17) |
C10A—S1A—N2A—C3A | −48.47 (17) | C10C—S1C—N2C—C3C | −47.31 (17) |
O2A—S1A—N2A—C13A | 33.4 (2) | O2C—S1C—N2C—C13C | 35.4 (2) |
O1A—S1A—N2A—C13A | −95.49 (19) | O1C—S1C—N2C—C13C | −93.42 (18) |
C10A—S1A—N2A—C13A | 150.28 (18) | C10C—S1C—N2C—C13C | 152.48 (18) |
C13A—N2A—C3A—N4A | −165.2 (2) | C13C—N2C—C3C—N4C | −167.4 (2) |
S1A—N2A—C3A—N4A | 34.6 (3) | S1C—N2C—C3C—N4C | 33.6 (3) |
C13A—N2A—C3A—N11A | 12.2 (3) | C13C—N2C—C3C—N11C | 10.1 (3) |
S1A—N2A—C3A—N11A | −147.97 (16) | S1C—N2C—C3C—N11C | −148.83 (16) |
N11A—C3A—N4A—C5A | −173.92 (19) | N11C—C3C—N4C—C5C | −173.97 (19) |
N2A—C3A—N4A—C5A | 3.4 (3) | N2C—C3C—N4C—C5C | 3.5 (3) |
C3A—N4A—C5A—C10A | −18.2 (3) | C3C—N4C—C5C—C6C | 163.9 (2) |
C3A—N4A—C5A—C6A | 162.5 (2) | C3C—N4C—C5C—C10C | −17.4 (3) |
N4A—C5A—C6A—C7A | −179.39 (19) | N4C—C5C—C6C—C7C | −178.82 (19) |
C10A—C5A—C6A—C7A | 1.2 (3) | C10C—C5C—C6C—C7C | 2.3 (3) |
C5A—C6A—C7A—C8A | 0.3 (3) | C5C—C6C—C7C—C8C | 0.0 (4) |
C6A—C7A—C8A—C9A | −1.8 (4) | C6C—C7C—C8C—C9C | −2.3 (4) |
C6A—C7A—C8A—Cl1A | 179.00 (17) | C6C—C7C—C8C—Cl1C | 178.72 (17) |
C7A—C8A—C9A—C10A | 1.5 (3) | C7C—C8C—C9C—C10C | 2.0 (3) |
Cl1A—C8A—C9A—C10A | −179.22 (16) | Cl1C—C8C—C9C—C10C | −179.02 (16) |
C8A—C9A—C10A—C5A | 0.1 (3) | C8C—C9C—C10C—C5C | 0.6 (3) |
C8A—C9A—C10A—S1A | −174.57 (16) | C8C—C9C—C10C—S1C | −174.16 (17) |
N4A—C5A—C10A—C9A | 179.21 (19) | N4C—C5C—C10C—C9C | 178.57 (19) |
C6A—C5A—C10A—C9A | −1.4 (3) | C6C—C5C—C10C—C9C | −2.7 (3) |
N4A—C5A—C10A—S1A | −5.9 (3) | N4C—C5C—C10C—S1C | −6.5 (3) |
C6A—C5A—C10A—S1A | 173.42 (16) | C6C—C5C—C10C—S1C | 172.24 (16) |
O2A—S1A—C10A—C9A | −36.3 (2) | O2C—S1C—C10C—C9C | −36.4 (2) |
O1A—S1A—C10A—C9A | 95.34 (18) | O1C—S1C—C10C—C9C | 95.12 (18) |
N2A—S1A—C10A—C9A | −150.06 (17) | N2C—S1C—C10C—C9C | −150.40 (17) |
O2A—S1A—C10A—C5A | 148.65 (16) | O2C—S1C—C10C—C5C | 148.48 (16) |
O1A—S1A—C10A—C5A | −79.69 (18) | O1C—S1C—C10C—C5C | −79.96 (18) |
N2A—S1A—C10A—C5A | 34.91 (17) | N2C—S1C—C10C—C5C | 34.52 (18) |
N4A—C3A—N11A—C12A | 5.9 (3) | N4C—C3C—N11C—C12C | 6.4 (3) |
N2A—C3A—N11A—C12A | −171.59 (19) | N2C—C3C—N11C—C12C | −171.3 (2) |
O2B—S1B—N2B—C3B | −166.15 (15) | O2D—S1D—N2D—C3D | −166.24 (15) |
O1B—S1B—N2B—C3B | 64.81 (17) | O1D—S1D—N2D—C3D | 64.84 (17) |
C10B—S1B—N2B—C3B | −49.07 (17) | C10D—S1D—N2D—C3D | −49.39 (17) |
O2B—S1B—N2B—C13B | 31.9 (2) | O2D—S1D—N2D—C13D | 34.7 (2) |
O1B—S1B—N2B—C13B | −97.10 (18) | O1D—S1D—N2D—C13D | −94.25 (18) |
C10B—S1B—N2B—C13B | 149.02 (17) | C10D—S1D—N2D—C13D | 151.52 (18) |
C13B—N2B—C3B—N4B | −163.6 (2) | C13D—N2D—C3D—N4D | −165.9 (2) |
S1B—N2B—C3B—N4B | 35.6 (3) | S1D—N2D—C3D—N4D | 36.2 (3) |
C13B—N2B—C3B—N11B | 13.8 (3) | C13D—N2D—C3D—N11D | 12.2 (3) |
S1B—N2B—C3B—N11B | −146.99 (16) | S1D—N2D—C3D—N11D | −145.80 (16) |
N11B—C3B—N4B—C5B | −174.83 (19) | N11D—C3D—N4D—C5D | −175.49 (19) |
N2B—C3B—N4B—C5B | 2.5 (3) | N2D—C3D—N4D—C5D | 2.5 (3) |
C3B—N4B—C5B—C6B | 163.8 (2) | C3D—N4D—C5D—C6D | 162.8 (2) |
C3B—N4B—C5B—C10B | −17.7 (3) | C3D—N4D—C5D—C10D | −18.4 (3) |
N4B—C5B—C6B—C7B | −178.43 (19) | N4D—C5D—C6D—C7D | −179.6 (2) |
C10B—C5B—C6B—C7B | 2.9 (3) | C10D—C5D—C6D—C7D | 1.5 (3) |
C5B—C6B—C7B—C8B | −0.2 (3) | C5D—C6D—C7D—C8D | 0.0 (4) |
C6B—C7B—C8B—C9B | −2.2 (4) | C6D—C7D—C8D—C9D | −1.5 (4) |
C6B—C7B—C8B—Cl1B | 178.00 (17) | C6D—C7D—C8D—Cl1D | 178.76 (17) |
C7B—C8B—C9B—C10B | 1.7 (3) | C7D—C8D—C9D—C10D | 1.3 (3) |
Cl1B—C8B—C9B—C10B | −178.49 (16) | Cl1D—C8D—C9D—C10D | −178.92 (16) |
C8B—C9B—C10B—C5B | 1.2 (3) | C8D—C9D—C10D—C5D | 0.3 (3) |
C8B—C9B—C10B—S1B | −174.26 (17) | C8D—C9D—C10D—S1D | −174.62 (17) |
N4B—C5B—C10B—C9B | 177.99 (19) | N4D—C5D—C10D—C9D | 179.47 (19) |
C6B—C5B—C10B—C9B | −3.4 (3) | C6D—C5D—C10D—C9D | −1.6 (3) |
N4B—C5B—C10B—S1B | −6.4 (3) | N4D—C5D—C10D—S1D | −5.4 (3) |
C6B—C5B—C10B—S1B | 172.19 (16) | C6D—C5D—C10D—S1D | 173.45 (16) |
O2B—S1B—C10B—C9B | −35.0 (2) | O2D—S1D—C10D—C9D | −36.2 (2) |
O1B—S1B—C10B—C9B | 96.97 (18) | O1D—S1D—C10D—C9D | 95.60 (19) |
N2B—S1B—C10B—C9B | −148.80 (17) | N2D—S1D—C10D—C9D | −149.76 (18) |
O2B—S1B—C10B—C5B | 149.25 (16) | O2D—S1D—C10D—C5D | 148.51 (16) |
O1B—S1B—C10B—C5B | −78.79 (18) | O1D—S1D—C10D—C5D | −79.69 (18) |
N2B—S1B—C10B—C5B | 35.44 (18) | N2D—S1D—C10D—C5D | 34.95 (18) |
N4B—C3B—N11B—C12B | 4.4 (3) | N4D—C3D—N11D—C12D | 3.4 (3) |
N2B—C3B—N11B—C12B | −173.12 (19) | N2D—C3D—N11D—C12D | −174.73 (19) |
Hydrogen-bond geometry (Å, º) top
D—H···A | D—H | H···A | D···A | D—H···A |
N11A—H11A···O1Bi | 0.78 (2) | 2.34 (2) | 3.093 (2) | 161 (2) |
N11B—H11B···O1Aii | 0.82 (2) | 2.27 (2) | 3.074 (2) | 165 (2) |
N11C—H11C···O1Diii | 0.84 (2) | 2.27 (2) | 3.058 (2) | 157 (2) |
N11D—H11D···O1Civ | 0.86 (2) | 2.20 (2) | 3.030 (2) | 162 (2) |
Symmetry codes: (i) −x+1, −y+1, −z; (ii) −x, −y+1, −z; (iii) −x+1, −y+1, −z+1; (iv) −x, −y+1, −z+1. |
Experimental details
Crystal data |
Chemical formula | C9H10ClN3O2S |
Mr | 259.71 |
Crystal system, space group | Monoclinic, P21/a |
Temperature (K) | 293 |
a, b, c (Å) | 10.096 (1), 26.316 (2), 16.927 (2) |
β (°) | 90.070 (2) |
V (Å3) | 4497.3 (8) |
Z | 16 |
Radiation type | Mo Kα |
µ (mm−1) | 0.51 |
Crystal size (mm) | 0.30 × 0.30 × 0.30 |
|
Data collection |
Diffractometer | MAR345 image-plate diffractometer |
Absorption correction | – |
No. of measured, independent and observed [I > 2σ(I)] reflections | 38152, 6008, 4970 |
Rint | 0.039 |
θmax (°) | 23.3 |
(sin θ/λ)max (Å−1) | 0.557 |
|
Refinement |
R[F2 > 2σ(F2)], wR(F2), S | 0.036, 0.106, 1.07 |
No. of reflections | 6008 |
No. of parameters | 598 |
H-atom treatment | H atoms treated by a mixture of independent and constrained refinement |
Δρmax, Δρmin (e Å−3) | 0.25, −0.27 |
Selected geometric parameters (Å, º) topS1A—O1A | 1.4322 (16) | S1C—O1C | 1.4332 (16) |
S1A—O2A | 1.4235 (16) | S1C—O2C | 1.4173 (16) |
S1A—N2A | 1.6461 (18) | S1C—N2C | 1.6509 (18) |
S1A—C10A | 1.727 (2) | S1C—C10C | 1.731 (2) |
N2A—C3A | 1.408 (3) | N2C—C3C | 1.402 (3) |
N2A—C13A | 1.470 (3) | N2C—C13C | 1.468 (3) |
C3A—N4A | 1.301 (3) | C3C—N4C | 1.307 (3) |
C3A—N11A | 1.337 (3) | C3C—N11C | 1.337 (3) |
N4A—C5A | 1.390 (3) | N4C—C5C | 1.386 (3) |
N11A—C12A | 1.446 (3) | N11C—C12C | 1.444 (3) |
S1B—O1B | 1.4376 (16) | S1D—O1D | 1.4340 (16) |
S1B—O2B | 1.4233 (15) | S1D—O2D | 1.4214 (15) |
S1B—N2B | 1.6526 (17) | S1D—N2D | 1.6508 (17) |
S1B—C10B | 1.725 (2) | S1D—C10D | 1.732 (2) |
N2B—C3B | 1.405 (2) | N2D—C3D | 1.406 (3) |
N2B—C13B | 1.461 (3) | N2D—C13D | 1.464 (3) |
C3B—N4B | 1.301 (3) | C3D—N4D | 1.309 (3) |
C3B—N11B | 1.336 (3) | C3D—N11D | 1.333 (3) |
N4B—C5B | 1.389 (3) | N4D—C5D | 1.386 (3) |
N11B—C12B | 1.452 (3) | N11D—C12D | 1.450 (3) |
| | | |
C3A—N2A—C13A | 122.90 (18) | C3C—N2C—C13C | 122.90 (18) |
C3A—N2A—S1A | 116.48 (13) | C3C—N2C—S1C | 116.88 (13) |
C13A—N2A—S1A | 117.70 (15) | C13C—N2C—S1C | 116.96 (15) |
N4A—C3A—N11A | 120.17 (19) | N4C—C3C—N11C | 119.81 (19) |
N4A—C3A—N2A | 123.69 (19) | N4C—C3C—N2C | 123.91 (19) |
N11A—C3A—N2A | 116.09 (17) | N11C—C3C—N2C | 116.24 (18) |
C3A—N4A—C5A | 119.55 (17) | C3C—N4C—C5C | 119.69 (18) |
C3A—N11A—C12A | 122.37 (19) | C3C—N11C—C12C | 122.19 (19) |
C3B—N2B—C13B | 123.56 (17) | C3D—N2D—C13D | 122.58 (17) |
C3B—N2B—S1B | 115.87 (13) | C3D—N2D—S1D | 116.17 (13) |
C13B—N2B—S1B | 117.82 (14) | C13D—N2D—S1D | 117.60 (14) |
N4B—C3B—N11B | 120.46 (19) | N4D—C3D—N11D | 120.38 (19) |
N4B—C3B—N2B | 123.93 (19) | N4D—C3D—N2D | 123.45 (19) |
N11B—C3B—N2B | 115.56 (18) | N11D—C3D—N2D | 116.14 (18) |
C3B—N4B—C5B | 119.71 (17) | C3D—N4D—C5D | 119.73 (17) |
C3B—N11B—C12B | 122.83 (19) | C3D—N11D—C12D | 122.86 (19) |
| | | |
S1A—N2A—C3A—N4A | 34.6 (3) | S1C—N2C—C3C—N4C | 33.6 (3) |
C13A—N2A—C3A—N11A | 12.2 (3) | C13C—N2C—C3C—N11C | 10.1 (3) |
N2A—C3A—N4A—C5A | 3.4 (3) | N2C—C3C—N4C—C5C | 3.5 (3) |
N2A—C3A—N11A—C12A | −171.59 (19) | N2C—C3C—N11C—C12C | −171.3 (2) |
S1B—N2B—C3B—N4B | 35.6 (3) | S1D—N2D—C3D—N4D | 36.2 (3) |
C13B—N2B—C3B—N11B | 13.8 (3) | C13D—N2D—C3D—N11D | 12.2 (3) |
N2B—C3B—N4B—C5B | 2.5 (3) | N2D—C3D—N4D—C5D | 2.5 (3) |
N2B—C3B—N11B—C12B | −173.12 (19) | N2D—C3D—N11D—C12D | −174.73 (19) |
Hydrogen-bond geometry (Å, º) top
D—H···A | D—H | H···A | D···A | D—H···A |
N11A—H11A···O1Bi | 0.78 (2) | 2.34 (2) | 3.093 (2) | 161 (2) |
N11B—H11B···O1Aii | 0.82 (2) | 2.27 (2) | 3.074 (2) | 165 (2) |
N11C—H11C···O1Diii | 0.84 (2) | 2.27 (2) | 3.058 (2) | 157 (2) |
N11D—H11D···O1Civ | 0.86 (2) | 2.20 (2) | 3.030 (2) | 162 (2) |
Symmetry codes: (i) −x+1, −y+1, −z; (ii) −x, −y+1, −z; (iii) −x+1, −y+1, −z+1; (iv) −x, −y+1, −z+1. |
Subscribe to Acta Crystallographica Section E: Crystallographic Communications
The full text of this article is available to subscribers to the journal.
If you have already registered and are using a computer listed in your registration details, please email
support@iucr.org for assistance.
The title compound is a structural analogue of diazoxide (7-chloro-3-methyl-4H-1,2,4-benzothiadiazine 1,1-dioxide; Bandoli & Nicolini, 1977) and other 3-alkylamino-7-chloro-4H-1,2,4-benzothiadiazine 1,1-dioxides known to exert important biological properties (smooth muscle myorelaxants and inhibitors of insulin release) like 7-chloro-(R/S)-3-[1-(cyclohexyl)ethylamino]-4H-1,2,4-benzothiadiazine 1,1-dioxide (Dupont et al., 1999). A typical 2H-tautomeric form results from the presence of the metyl substituent in the 2-position of the thiadiazine ring. There are four independent molecules (A, B, C and D) in the asymmetric unit with essentially identical geometry: even the most flexible N2—C3—N11—C12 torsion angles do not deviate from the mean value of -172.7 (2)° by more than 2.1 (2)°. The C3—N2 (A—D) distances are within the range 1.402 (3)–1.408 (3) Å, and C3—N4 within 1.301 (3)–1.309 (3) Å. They are useful references with respect to C3—N2 single- and C3—N4 double-bond length in such a ring system. The corresponding distances in diazoxide are 1.300 (9) and 1.335 (9) Å, respectively, and 1.325 (5) and 1.368 (4) Å in 7-chloro-(S)-3-[1-(cyclohexyl)ethylamino]-4H-1,2,4-benzothiadiazine 1,1-dioxide (Dupont et al., 1999). Typical values for C3—N2 double-bond [1.326 (4)] and C3—N4 single-bond [1.381 (4) Å] have been observed in the molecular structure of 3-isopropylamino-4-methyl-4H-pyrido[4,3 e][1,2,4]thiadiazine 1,1-dioxide (Dupont et al., 1996) where a 4H-tautomeric form is imposed by a 4-methyl substituent.
The crystal packing is dominated by two symmetry independent types of hydrogen-bonded infinite chains. The chains of the first type are made up of alternating A and B molecules linked via N—H···O bonds formed by the methylamino NH groups and sulfoxide oxygen atoms. The chains of the second type are built in the analogous way and involve alternating C and D molecules. Both chains are stretching along the shortest axis, i.e. a, of the unit cell.