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The title compound, C14H16N4O2S2·H2O, is a member of a new series of imidazo[2,1-b]thiazoles. The crystal packing is stabilized by intermolecular hydrogen bonds.
Supporting information
CCDC reference: 282382
Key indicators
- Single-crystal X-ray study
- T = 100 K
- Mean (C-C) = 0.002 Å
- R factor = 0.034
- wR factor = 0.076
- Data-to-parameter ratio = 15.6
checkCIF/PLATON results
No syntax errors found
Alert level C
PLAT029_ALERT_3_C _diffrn_measured_fraction_theta_full Low ....... 0.96
PLAT322_ALERT_2_C Check Hybridisation of S1 in Main Residue . ?
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
1 ALERT type 2 Indicator that the structure model may be wrong or deficient
1 ALERT type 3 Indicator that the structure quality may be low
0 ALERT type 4 Improvement, methodology, query or suggestion
Data collection: COLLECT (Nonius, 1999); cell refinement: EVALCCD (Duisenberg et al., 2003); data reduction: SADABS (Sheldrick, 2002); program(s) used to solve structure: SIR97 (Altomare et al., 1999); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997); software used to prepare material for publication: WinGX (Farrugia, 1999).
6-Methyl-
N-(3-oxo-1-thia-4-azaspiro[4.4]non-4-yl)imidazo[2,1-
b][1,3]thiazole- 5-carboxamide monohydrate
top
Crystal data top
C14H16N4O2S2·H2O | F(000) = 1488 |
Mr = 354.46 | Dx = 1.400 Mg m−3 |
Orthorhombic, Pbca | Mo Kα radiation, λ = 0.71069 Å |
Hall symbol: -P 2ac 2ab | Cell parameters from 338 reflections |
a = 12.959 (5) Å | θ = 6.0–20.0° |
b = 10.908 (5) Å | µ = 0.34 mm−1 |
c = 23.797 (5) Å | T = 100 K |
V = 3364 (2) Å3 | Prism, colourless |
Z = 8 | 0.35 × 0.24 × 0.14 mm |
Data collection top
Bruker Nonius KappaCCD area-detector diffractometer | 4118 independent reflections |
Radiation source: fine-focus sealed tube | 3269 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.033 |
Detector resolution: 9 pixels mm-1 | θmax = 28.5°, θmin = 3.4° |
ω scans | h = −17→17 |
Absorption correction: multi-scan (SADABS; Sheldrick, 2002) | k = −14→14 |
Tmin = 0.891, Tmax = 0.955 | l = −29→31 |
32544 measured reflections | |
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) = 0.076 | H atoms treated by a mixture of independent and constrained refinement |
S = 1.04 | w = 1/[σ2(Fo2) + (0.0323P)2 + 1.4591P] where P = (Fo2 + 2Fc2)/3 |
4118 reflections | (Δ/σ)max = 0.001 |
264 parameters | Δρmax = 0.29 e Å−3 |
0 restraints | Δρmin = −0.23 e Å−3 |
Special details top
Geometry. Bond distances, angles etc. have been calculated using the rounded
fractional coordinates. All su's are estimated from the variances of the
(full) variance-covariance matrix. The cell e.s.d.'s are taken into account in
the estimation of distances, angles and torsion angles |
Refinement. Refinement on F2 for ALL reflections except those flagged by the user
for potential systematic errors. Weighted R-factors wR and all
goodnesses of fit S are based on F2, conventional
R-factors R are based on F, with F set to zero for
negative F2. The observed criterion of F2 > σ(F2)
is used only for calculating -R-factor-obs 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 | 0.47312 (4) | 0.72384 (3) | 0.53705 (1) | 0.0296 (1) | |
S2 | 0.62994 (3) | −0.04989 (3) | 0.71710 (2) | 0.0256 (1) | |
O1 | 0.62905 (8) | 0.31537 (9) | 0.62365 (4) | 0.0229 (3) | |
O2 | 0.61153 (9) | 0.03329 (10) | 0.55917 (4) | 0.0318 (3) | |
O3 | 0.35228 (9) | 0.10205 (10) | 0.53984 (4) | 0.0245 (3) | |
N1 | 0.34127 (10) | 0.53845 (11) | 0.57934 (5) | 0.0233 (4) | |
N2 | 0.51176 (9) | 0.50768 (10) | 0.57351 (4) | 0.0182 (3) | |
N3 | 0.48705 (9) | 0.18938 (10) | 0.62017 (5) | 0.0168 (3) | |
N4 | 0.54470 (9) | 0.09398 (10) | 0.64301 (4) | 0.0171 (3) | |
C1 | 0.27995 (12) | 0.34277 (14) | 0.62162 (7) | 0.0286 (5) | |
C2 | 0.36446 (11) | 0.42210 (12) | 0.59894 (6) | 0.0206 (4) | |
C3 | 0.43119 (12) | 0.58534 (12) | 0.56448 (5) | 0.0220 (4) | |
C4 | 0.59970 (14) | 0.66950 (14) | 0.53885 (6) | 0.0291 (5) | |
C5 | 0.60822 (12) | 0.55494 (13) | 0.55886 (6) | 0.0228 (4) | |
C6 | 0.46929 (11) | 0.39983 (12) | 0.59538 (5) | 0.0171 (4) | |
C7 | 0.53737 (10) | 0.29958 (11) | 0.61324 (5) | 0.0163 (3) | |
C8 | 0.60205 (11) | 0.01971 (12) | 0.60988 (6) | 0.0221 (4) | |
C9 | 0.64814 (15) | −0.08377 (15) | 0.64338 (7) | 0.0324 (5) | |
C10 | 0.53538 (11) | 0.07321 (11) | 0.70366 (5) | 0.0161 (4) | |
C11 | 0.42530 (11) | 0.03973 (13) | 0.72272 (6) | 0.0219 (4) | |
C12 | 0.41831 (14) | 0.08223 (16) | 0.78454 (6) | 0.0302 (5) | |
C13 | 0.52176 (13) | 0.14569 (14) | 0.79753 (6) | 0.0261 (4) | |
C14 | 0.56245 (12) | 0.18480 (12) | 0.73989 (5) | 0.0210 (4) | |
H1A | 0.3052 (15) | 0.2898 (16) | 0.6527 (8) | 0.0380* | |
H1B | 0.2214 (15) | 0.3942 (16) | 0.6323 (8) | 0.0380* | |
H1C | 0.2572 (14) | 0.2897 (16) | 0.5926 (8) | 0.0380* | |
H3 | 0.4388 (14) | 0.1629 (16) | 0.5950 (7) | 0.0310* | |
H4 | 0.6507 (14) | 0.7222 (16) | 0.5269 (7) | 0.0310* | |
H5 | 0.6653 (14) | 0.5075 (16) | 0.5643 (7) | 0.0310* | |
H9A | 0.6102 (13) | −0.1615 (17) | 0.6319 (7) | 0.0310* | |
H9B | 0.7186 (15) | −0.0884 (15) | 0.6367 (7) | 0.0310* | |
H11A | 0.3757 (13) | 0.0873 (16) | 0.6972 (7) | 0.0310* | |
H11B | 0.4108 (14) | −0.0484 (17) | 0.7161 (7) | 0.0310* | |
H12A | 0.3607 (14) | 0.1372 (16) | 0.7894 (7) | 0.0310* | |
H12B | 0.4064 (13) | 0.0166 (16) | 0.8080 (8) | 0.0310* | |
H13A | 0.5147 (13) | 0.2149 (16) | 0.8240 (7) | 0.0310* | |
H13B | 0.5742 (14) | 0.0916 (16) | 0.8143 (7) | 0.0310* | |
H14A | 0.6366 (14) | 0.2048 (15) | 0.7387 (7) | 0.0310* | |
H14B | 0.5200 (13) | 0.2584 (16) | 0.7262 (7) | 0.0310* | |
H31 | 0.3706 (15) | 0.0553 (18) | 0.5128 (9) | 0.042 (6)* | |
H32 | 0.2979 (17) | 0.0806 (19) | 0.5512 (9) | 0.044 (6)* | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
S1 | 0.0495 (3) | 0.0205 (2) | 0.0189 (2) | 0.0087 (2) | −0.0009 (2) | 0.0051 (1) |
S2 | 0.0266 (2) | 0.0198 (2) | 0.0304 (2) | 0.0081 (1) | −0.0033 (2) | 0.0043 (1) |
O1 | 0.0168 (5) | 0.0232 (5) | 0.0288 (5) | 0.0012 (4) | −0.0023 (4) | 0.0054 (4) |
O2 | 0.0398 (7) | 0.0324 (6) | 0.0233 (5) | 0.0066 (5) | 0.0123 (5) | −0.0038 (4) |
O3 | 0.0221 (6) | 0.0290 (5) | 0.0223 (5) | −0.0104 (5) | 0.0057 (4) | −0.0071 (4) |
N1 | 0.0240 (7) | 0.0234 (6) | 0.0224 (6) | 0.0086 (5) | −0.0079 (5) | −0.0063 (5) |
N2 | 0.0233 (7) | 0.0176 (5) | 0.0138 (5) | 0.0042 (5) | −0.0022 (4) | 0.0002 (4) |
N3 | 0.0178 (6) | 0.0174 (5) | 0.0153 (5) | 0.0031 (4) | −0.0032 (4) | 0.0001 (4) |
N4 | 0.0195 (6) | 0.0154 (5) | 0.0163 (5) | 0.0049 (4) | −0.0004 (4) | −0.0008 (4) |
C1 | 0.0179 (8) | 0.0257 (8) | 0.0421 (9) | 0.0013 (6) | −0.0005 (7) | −0.0089 (7) |
C2 | 0.0212 (8) | 0.0204 (6) | 0.0201 (6) | 0.0047 (5) | −0.0056 (5) | −0.0068 (5) |
C3 | 0.0321 (9) | 0.0200 (6) | 0.0138 (6) | 0.0085 (6) | −0.0063 (5) | −0.0017 (5) |
C4 | 0.0400 (10) | 0.0275 (7) | 0.0197 (6) | −0.0016 (7) | 0.0061 (6) | 0.0052 (6) |
C5 | 0.0276 (8) | 0.0240 (7) | 0.0169 (6) | 0.0001 (6) | 0.0032 (5) | 0.0031 (5) |
C6 | 0.0182 (7) | 0.0178 (6) | 0.0153 (6) | 0.0007 (5) | −0.0028 (5) | −0.0011 (5) |
C7 | 0.0164 (7) | 0.0192 (6) | 0.0134 (5) | 0.0027 (5) | 0.0006 (5) | 0.0003 (5) |
C8 | 0.0202 (8) | 0.0201 (6) | 0.0261 (7) | 0.0016 (5) | 0.0058 (6) | −0.0029 (5) |
C9 | 0.0351 (10) | 0.0269 (8) | 0.0353 (8) | 0.0132 (7) | 0.0156 (7) | 0.0028 (7) |
C10 | 0.0180 (7) | 0.0142 (6) | 0.0161 (6) | 0.0026 (5) | −0.0009 (5) | 0.0019 (5) |
C11 | 0.0203 (8) | 0.0231 (7) | 0.0223 (7) | −0.0007 (6) | 0.0005 (6) | 0.0048 (5) |
C12 | 0.0348 (10) | 0.0342 (8) | 0.0217 (7) | 0.0006 (7) | 0.0085 (6) | 0.0051 (6) |
C13 | 0.0357 (9) | 0.0273 (7) | 0.0154 (6) | 0.0044 (7) | −0.0016 (6) | 0.0004 (6) |
C14 | 0.0263 (8) | 0.0190 (6) | 0.0176 (6) | 0.0004 (6) | −0.0027 (6) | −0.0013 (5) |
Geometric parameters (Å, º) top
S1—C3 | 1.7332 (16) | C8—C9 | 1.505 (2) |
S1—C4 | 1.745 (2) | C10—C14 | 1.5323 (19) |
S2—C9 | 1.8082 (19) | C10—C11 | 1.541 (2) |
S2—C10 | 1.8458 (16) | C11—C12 | 1.545 (2) |
O1—C7 | 1.2258 (17) | C12—C13 | 1.540 (3) |
O2—C8 | 1.2220 (18) | C13—C14 | 1.530 (2) |
O3—H31 | 0.86 (2) | C1—H1C | 0.948 (18) |
O3—H32 | 0.79 (2) | C1—H1B | 0.977 (19) |
N1—C2 | 1.3851 (19) | C1—H1A | 0.994 (19) |
N1—C3 | 1.321 (2) | C4—H4 | 0.921 (18) |
N2—C5 | 1.396 (2) | C5—H5 | 0.912 (18) |
N2—C3 | 1.3616 (19) | C9—H9A | 1.018 (18) |
N2—C6 | 1.3992 (18) | C9—H9B | 0.928 (19) |
N3—N4 | 1.3916 (17) | C11—H11A | 1.025 (17) |
N3—C7 | 1.3775 (18) | C11—H11B | 0.992 (18) |
N4—C10 | 1.4659 (17) | C12—H12B | 0.921 (18) |
N4—C8 | 1.3529 (19) | C12—H12A | 0.965 (18) |
N3—H3 | 0.913 (17) | C13—H13A | 0.988 (17) |
C1—C2 | 1.497 (2) | C13—H13B | 0.985 (18) |
C2—C6 | 1.383 (2) | C14—H14B | 1.026 (17) |
C4—C5 | 1.342 (2) | C14—H14A | 0.986 (18) |
C6—C7 | 1.4679 (19) | | |
| | | |
S1···C7i | 3.588 (2) | C8···O1 | 3.261 (2) |
S1···O3i | 3.475 (2) | C9···O1viii | 3.125 (3) |
S1···C6i | 3.508 (2) | C13···C3iii | 3.404 (2) |
S2···N4 | 2.6060 (16) | C13···N2iii | 3.446 (2) |
S1···H9Aii | 3.133 (17) | C14···O1 | 3.229 (2) |
S2···H13B | 2.873 (17) | C14···C7 | 3.280 (2) |
S2···H14Biii | 3.157 (17) | C1···H3 | 2.914 (18) |
O1···N2 | 2.852 (2) | C2···H32ix | 2.95 (2) |
O1···N4 | 2.6905 (19) | C2···H13Bvii | 2.883 (17) |
O1···C5 | 3.046 (2) | C2···H3 | 2.988 (18) |
O1···C8 | 3.261 (2) | C3···H13Avii | 3.087 (17) |
O1···C14 | 3.229 (2) | C3···H32ix | 2.99 (2) |
O1···C9iv | 3.125 (3) | C3···H13Bvii | 2.886 (17) |
O2···O3v | 2.8197 (19) | C4···H9Aii | 2.884 (18) |
O2···N3 | 2.758 (2) | C6···H12Bvii | 3.083 (18) |
O2···C7 | 3.319 (2) | C6···H13Bvii | 3.052 (17) |
O3···C4i | 3.179 (2) | C7···H5 | 3.041 (18) |
O3···S1i | 3.475 (2) | C7···H14B | 2.735 (17) |
O3···C1 | 3.400 (2) | C8···H31v | 3.05 (2) |
O3···N1vi | 2.767 (2) | H1A···N3 | 2.712 (19) |
O3···N3 | 2.759 (2) | H1C···O3 | 2.699 (18) |
O3···O2v | 2.8197 (19) | H1C···H32 | 2.54 (3) |
O1···H9Biv | 2.258 (19) | H3···O2 | 2.781 (18) |
O1···H14B | 2.888 (17) | H3···O3 | 1.850 (17) |
O1···H5 | 2.571 (17) | H3···C1 | 2.914 (18) |
O1···H12Bvii | 2.770 (18) | H3···C2 | 2.988 (18) |
O2···H5viii | 2.908 (18) | H3···H31 | 2.45 (3) |
O2···H31v | 1.98 (2) | H3···H32 | 2.29 (3) |
O2···H3 | 2.781 (18) | H4···O3i | 2.490 (17) |
O3···H3 | 1.850 (17) | H5···O2iv | 2.908 (18) |
O3···H4i | 2.490 (17) | H5···H9Biv | 2.52 (2) |
O3···H1C | 2.699 (18) | H5···C7 | 3.041 (18) |
N1···O3ix | 2.767 (2) | H5···O1 | 2.571 (17) |
N1···N2 | 2.239 (2) | H9A···S1x | 3.133 (17) |
N2···O1 | 2.852 (2) | H9A···C4x | 2.884 (18) |
N2···C13vii | 3.446 (2) | H9A···H13Aiii | 2.35 (2) |
N3···O3 | 2.759 (2) | H9B···O1viii | 2.258 (19) |
N3···O2 | 2.758 (2) | H9B···H5viii | 2.52 (2) |
N3···C1 | 3.163 (2) | H11A···N3 | 2.585 (17) |
N4···O1 | 2.6905 (19) | H12B···O1iii | 2.770 (18) |
N4···S2 | 2.6060 (16) | H12B···C6iii | 3.083 (18) |
N1···H13Bvii | 2.818 (17) | H13A···H9Avii | 2.35 (2) |
N1···H32ix | 1.98 (2) | H13A···C3iii | 3.087 (17) |
N3···H1A | 2.712 (19) | H13B···S2 | 2.873 (17) |
N3···H11A | 2.585 (17) | H13B···C3iii | 2.886 (17) |
N3···H14B | 2.668 (17) | H13B···C6iii | 3.052 (17) |
C1···O3 | 3.400 (2) | H13B···N1iii | 2.818 (17) |
C1···N3 | 3.163 (2) | H13B···C2iii | 2.883 (17) |
C2···C4i | 3.459 (3) | H14B···O1 | 2.888 (17) |
C3···C13vii | 3.404 (2) | H14B···S2vii | 3.157 (17) |
C3···C5i | 3.349 (2) | H14B···N3 | 2.668 (17) |
C4···C2i | 3.459 (3) | H14B···C7 | 2.735 (17) |
C4···C6i | 3.402 (2) | H31···H3 | 2.45 (3) |
C4···O3i | 3.179 (2) | H31···O2v | 1.98 (2) |
C5···C3i | 3.349 (2) | H31···C8v | 3.05 (2) |
C5···O1 | 3.046 (2) | H32···H1C | 2.54 (3) |
C6···C4i | 3.402 (2) | H32···H3 | 2.29 (3) |
C6···S1i | 3.508 (2) | H32···N1vi | 1.98 (2) |
C7···C14 | 3.280 (2) | H32···C2vi | 2.95 (2) |
C7···S1i | 3.588 (2) | H32···C3vi | 2.99 (2) |
C7···O2 | 3.319 (2) | | |
| | | |
C3—S1—C4 | 89.39 (7) | C11—C12—C13 | 105.96 (12) |
C9—S2—C10 | 93.85 (7) | C12—C13—C14 | 104.20 (12) |
H31—O3—H32 | 109 (2) | C10—C14—C13 | 101.77 (11) |
C2—N1—C3 | 104.69 (12) | C2—C1—H1A | 111.3 (11) |
C3—N2—C5 | 114.67 (11) | C2—C1—H1C | 108.5 (11) |
C3—N2—C6 | 106.27 (11) | H1A—C1—H1B | 113.3 (16) |
C5—N2—C6 | 139.06 (12) | C2—C1—H1B | 109.3 (11) |
N4—N3—C7 | 116.44 (11) | H1B—C1—H1C | 107.4 (16) |
N3—N4—C8 | 121.01 (10) | H1A—C1—H1C | 106.8 (15) |
N3—N4—C10 | 117.12 (10) | C5—C4—H4 | 129.2 (11) |
C8—N4—C10 | 121.77 (11) | S1—C4—H4 | 117.1 (11) |
C7—N3—H3 | 121.5 (11) | N2—C5—H5 | 118.8 (11) |
N4—N3—H3 | 112.8 (11) | C4—C5—H5 | 130.2 (11) |
N1—C2—C6 | 110.70 (12) | S2—C9—H9B | 107.8 (10) |
N1—C2—C1 | 119.50 (13) | C8—C9—H9A | 106.9 (10) |
C1—C2—C6 | 129.76 (13) | S2—C9—H9A | 111.6 (10) |
N1—C3—N2 | 113.16 (12) | H9A—C9—H9B | 112.6 (14) |
S1—C3—N2 | 111.18 (11) | C8—C9—H9B | 109.9 (10) |
S1—C3—N1 | 135.64 (12) | C10—C11—H11A | 106.6 (10) |
S1—C4—C5 | 113.73 (13) | C10—C11—H11B | 111.0 (10) |
N2—C5—C4 | 111.02 (14) | C12—C11—H11B | 115.5 (10) |
N2—C6—C2 | 105.16 (11) | H11A—C11—H11B | 106.1 (14) |
N2—C6—C7 | 119.84 (12) | C12—C11—H11A | 112.1 (10) |
C2—C6—C7 | 134.72 (12) | C11—C12—H12B | 110.7 (12) |
O1—C7—N3 | 123.87 (12) | C13—C12—H12A | 111.7 (11) |
N3—C7—C6 | 113.59 (11) | C13—C12—H12B | 111.9 (11) |
O1—C7—C6 | 122.44 (12) | H12A—C12—H12B | 106.3 (15) |
O2—C8—C9 | 125.03 (13) | C11—C12—H12A | 110.3 (10) |
N4—C8—C9 | 111.00 (12) | C12—C13—H13B | 114.4 (10) |
O2—C8—N4 | 123.93 (13) | C14—C13—H13A | 113.0 (10) |
S2—C9—C8 | 107.98 (11) | C12—C13—H13A | 113.0 (10) |
S2—C10—C14 | 109.17 (9) | H13A—C13—H13B | 105.3 (14) |
S2—C10—N4 | 103.20 (8) | C14—C13—H13B | 107.0 (10) |
C11—C10—C14 | 103.57 (11) | C10—C14—H14A | 112.5 (10) |
S2—C10—C11 | 113.03 (9) | C10—C14—H14B | 108.7 (10) |
N4—C10—C11 | 113.75 (11) | C13—C14—H14B | 108.5 (9) |
N4—C10—C14 | 114.35 (10) | H14A—C14—H14B | 109.9 (14) |
C10—C11—C12 | 105.27 (12) | C13—C14—H14A | 115.1 (10) |
| | | |
C3—S1—C4—C5 | −0.02 (12) | N3—N4—C10—S2 | −175.64 (9) |
C4—S1—C3—N2 | 0.17 (10) | C8—N4—C10—C14 | 126.50 (14) |
C4—S1—C3—N1 | 178.87 (15) | C8—N4—C10—C11 | −114.78 (14) |
C9—S2—C10—C11 | 111.17 (10) | C10—N4—C8—O2 | 179.64 (13) |
C9—S2—C10—C14 | −134.14 (10) | N3—N4—C8—O2 | 3.5 (2) |
C9—S2—C10—N4 | −12.14 (10) | N3—N4—C10—C14 | −57.19 (16) |
C10—S2—C9—C8 | 13.87 (12) | N3—N4—C8—C9 | −174.09 (12) |
C2—N1—C3—N2 | −0.52 (15) | C1—C2—C6—C7 | −3.2 (3) |
C2—N1—C3—S1 | −179.20 (12) | C1—C2—C6—N2 | −176.91 (14) |
C3—N1—C2—C1 | 177.80 (13) | N1—C2—C6—C7 | 174.60 (13) |
C3—N1—C2—C6 | −0.26 (15) | N1—C2—C6—N2 | 0.89 (15) |
C6—N2—C5—C4 | 179.73 (14) | S1—C4—C5—N2 | −0.12 (17) |
C6—N2—C3—N1 | 1.07 (14) | N2—C6—C7—N3 | −164.32 (11) |
C5—N2—C6—C7 | 4.5 (2) | C2—C6—C7—N3 | 22.7 (2) |
C5—N2—C3—N1 | −179.29 (11) | C2—C6—C7—O1 | −153.75 (15) |
C3—N2—C5—C4 | 0.26 (16) | N2—C6—C7—O1 | 19.25 (18) |
C3—N2—C6—C7 | −176.00 (11) | N4—C8—C9—S2 | −11.53 (16) |
C3—N2—C6—C2 | −1.15 (13) | O2—C8—C9—S2 | 170.95 (13) |
C5—N2—C6—C2 | 179.35 (14) | C11—C10—C14—C13 | 42.92 (13) |
C6—N2—C3—S1 | −179.91 (8) | N4—C10—C14—C13 | 167.26 (12) |
C5—N2—C3—S1 | −0.28 (13) | N4—C10—C11—C12 | −153.44 (11) |
N4—N3—C7—O1 | 3.27 (18) | S2—C10—C11—C12 | 89.30 (12) |
C7—N3—N4—C8 | −87.27 (15) | S2—C10—C14—C13 | −77.74 (12) |
N4—N3—C7—C6 | −173.10 (10) | C14—C10—C11—C12 | −28.71 (13) |
C7—N3—N4—C10 | 96.40 (14) | C10—C11—C12—C13 | 3.50 (15) |
C8—N4—C10—S2 | 8.05 (15) | C11—C12—C13—C14 | 23.08 (16) |
C10—N4—C8—C9 | 2.08 (18) | C12—C13—C14—C10 | −40.72 (14) |
N3—N4—C10—C11 | 61.52 (14) | | |
Symmetry codes: (i) −x+1, −y+1, −z+1; (ii) x, y+1, z; (iii) −x+1, y−1/2, −z+3/2; (iv) −x+3/2, y+1/2, z; (v) −x+1, −y, −z+1; (vi) −x+1/2, y−1/2, z; (vii) −x+1, y+1/2, −z+3/2; (viii) −x+3/2, y−1/2, z; (ix) −x+1/2, y+1/2, z; (x) x, y−1, z. |
Hydrogen-bond geometry (Å, º) top
D—H···A | D—H | H···A | D···A | D—H···A |
N3—H3···O3 | 0.913 (17) | 1.850 (17) | 2.759 (2) | 174.0 (17) |
O3—H31···O2v | 0.86 (2) | 1.98 (2) | 2.8197 (19) | 167.1 (19) |
O3—H32···N1vi | 0.79 (2) | 1.98 (2) | 2.767 (2) | 176 (2) |
Symmetry codes: (v) −x+1, −y, −z+1; (vi) −x+1/2, y−1/2, z. |
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