Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536806015121/dn2032sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S1600536806015121/dn2032Isup2.hkl |
CCDC reference: 610756
Key indicators
- Single-crystal X-ray study
- T = 295 K
- Mean (C-C) = 0.002 Å
- R factor = 0.043
- wR factor = 0.122
- Data-to-parameter ratio = 26.8
checkCIF/PLATON results
No syntax errors found
Alert level C PLAT041_ALERT_1_C Calc. and Rep. SumFormula Strings Differ .... ? PLAT042_ALERT_1_C Calc. and Rep. MoietyFormula Strings Differ .... ? PLAT045_ALERT_1_C Calculated and Reported Z Differ by ............ 0.50 Ratio PLAT063_ALERT_3_C Crystal Probably too Large for Beam Size ....... 0.80 mm PLAT142_ALERT_4_C su on b - Axis Small or Missing (x 100000) ..... 10 Ang. PLAT143_ALERT_4_C su on c - Axis Small or Missing (x 100000) ..... 10 Ang. PLAT220_ALERT_2_C Large Non-Solvent C Ueq(max)/Ueq(min) ... 2.83 Ratio PLAT222_ALERT_3_C Large Non-Solvent H Ueq(max)/Ueq(min) ... 3.39 Ratio PLAT720_ALERT_4_C Number of Unusual/Non-Standard Label(s) ........ 11
0 ALERT level A = In general: serious problem 0 ALERT level B = Potentially serious problem 9 ALERT level C = Check and explain 0 ALERT level G = General alerts; check 3 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 2 ALERT type 3 Indicator that the structure quality may be low 3 ALERT type 4 Improvement, methodology, query or suggestion
Data collection: SMART (Siemens, 1995); cell refinement: SAINT (Siemens, 1995); data reduction: SAINT and SADABS (Sheldrick, 2002); program(s) used to solve structure: SHELXTL (Bruker, 2001); program(s) used to refine structure: SHELXTL; molecular graphics: DIAMOND (Brandenburg, 2006); software used to prepare material for publication: SHELXTL.
C11H13N2O2S | F(000) = 992 |
Mr = 236.29 | Dx = 1.444 Mg m−3 |
Monoclinic, P21/c | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: -P 2ybc | Cell parameters from 8054 reflections |
a = 7.8750 (1) Å | θ = 1.9–33.1° |
b = 12.5588 (1) Å | µ = 0.28 mm−1 |
c = 22.0210 (1) Å | T = 295 K |
β = 93.645 (1)° | Plate, colorless |
V = 2173.48 (3) Å3 | 0.80 × 0.34 × 0.16 mm |
Z = 8 |
Siemens SMART CCD area-detector diffractometer | 7839 independent reflections |
Radiation source: fine-focus sealed tube | 5889 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.028 |
ω scans | θmax = 33.1°, θmin = 1.9° |
Absorption correction: multi-scan (SADABS; Sheldrick, 2002) | h = −12→11 |
Tmin = 0.805, Tmax = 0.956 | k = −18→19 |
33031 measured reflections | l = −32→33 |
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)] = 0.043 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.122 | H-atom parameters constrained |
S = 1.02 | w = 1/[σ2(Fo2) + (0.0601P)2 + 0.6348P] where P = (Fo2 + 2Fc2)/3 |
7839 reflections | (Δ/σ)max = 0.001 |
292 parameters | Δρmax = 0.35 e Å−3 |
0 restraints | Δρmin = −0.25 e Å−3 |
Experimental. Data were collected at low temperature using a Siemens SMART CCD diffractometer equiped with a LT-2 device. A full sphere of reciprocal space was scanned by 0.3° steps in ω with a crystal–to–detector distance of 3.97 cm, 20 s per frame. Preliminary orientation matrix was obtained from the first 100 frames using SMART (Siemens, 1995). The collected frames were integrated using the preliminary orientation matrix which was updated every 100 frames. Final cell parameters were obtained by refinement on the position of 8054 reflections with I>10σ(I) after integration of all the frames data using SAINT (Siemens, 1995). |
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. |
x | y | z | Uiso*/Ueq | ||
S1A | 0.08001 (4) | 0.14520 (2) | 0.317964 (15) | 0.02994 (8) | |
O1A | 0.27260 (15) | 0.33575 (8) | 0.30046 (5) | 0.0402 (2) | |
H1A | 0.3162 | 0.3913 | 0.2896 | 0.060* | |
O2A | 0.18832 (17) | 0.43621 (9) | 0.37607 (6) | 0.0515 (3) | |
N1A | −0.10571 (14) | 0.28598 (8) | 0.24352 (5) | 0.0281 (2) | |
H1A1 | −0.1184 | 0.3339 | 0.2707 | 0.034* | |
N3A | −0.02577 (14) | 0.13919 (8) | 0.19978 (5) | 0.0283 (2) | |
H3A | 0.0212 | 0.0783 | 0.1946 | 0.034* | |
C1A | 0.18635 (18) | 0.35400 (10) | 0.34762 (6) | 0.0303 (3) | |
C2A | 0.07637 (17) | 0.26154 (10) | 0.36737 (6) | 0.0285 (2) | |
H2A | −0.0414 | 0.2868 | 0.3671 | 0.034* | |
C3A | 0.13118 (19) | 0.22761 (13) | 0.43274 (6) | 0.0382 (3) | |
H3A1 | 0.1114 | 0.2864 | 0.4600 | 0.046* | |
H3A2 | 0.0604 | 0.1686 | 0.4441 | 0.046* | |
C4A | 0.3168 (2) | 0.19444 (18) | 0.44140 (8) | 0.0540 (4) | |
H4A1 | 0.3367 | 0.1342 | 0.4159 | 0.081* | |
H4A2 | 0.3429 | 0.1756 | 0.4832 | 0.081* | |
H4A3 | 0.3881 | 0.2525 | 0.4305 | 0.081* | |
C5A | −0.02016 (15) | 0.19441 (10) | 0.25187 (6) | 0.0255 (2) | |
C6A | −0.12042 (16) | 0.19674 (10) | 0.15546 (6) | 0.0282 (2) | |
C7A | −0.1669 (2) | 0.17585 (12) | 0.09474 (6) | 0.0381 (3) | |
H7A | −0.1334 | 0.1139 | 0.0757 | 0.046* | |
C8A | −0.2660 (2) | 0.25228 (13) | 0.06417 (7) | 0.0453 (4) | |
H8A | −0.3001 | 0.2411 | 0.0235 | 0.054* | |
C9A | −0.3164 (2) | 0.34558 (13) | 0.09245 (8) | 0.0445 (4) | |
H9A | −0.3833 | 0.3946 | 0.0701 | 0.053* | |
C10A | −0.26966 (18) | 0.36691 (11) | 0.15269 (7) | 0.0366 (3) | |
H10A | −0.3027 | 0.4291 | 0.1716 | 0.044* | |
C11A | −0.17023 (16) | 0.29018 (10) | 0.18348 (6) | 0.0277 (2) | |
S1B | 0.57038 (4) | 0.64591 (2) | 0.307055 (16) | 0.03188 (9) | |
O1B | 0.82333 (13) | 0.45993 (7) | 0.30577 (5) | 0.0334 (2) | |
O2B | 0.64773 (16) | 0.35096 (8) | 0.34996 (6) | 0.0442 (3) | |
N1B | 0.43777 (15) | 0.64400 (9) | 0.19195 (5) | 0.0317 (2) | |
H1B | 0.4732 | 0.7075 | 0.1855 | 0.038* | |
N3B | 0.39265 (14) | 0.49195 (8) | 0.24066 (5) | 0.0284 (2) | |
C1B | 0.69454 (16) | 0.44082 (9) | 0.33593 (6) | 0.0272 (2) | |
C2B | 0.59402 (17) | 0.53502 (10) | 0.35966 (6) | 0.0274 (2) | |
H2B | 0.4809 | 0.5102 | 0.3693 | 0.033* | |
C3B | 0.6853 (2) | 0.58213 (12) | 0.41747 (6) | 0.0405 (3) | |
H3B1 | 0.7886 | 0.6174 | 0.4066 | 0.049* | |
H3B2 | 0.6125 | 0.6354 | 0.4344 | 0.049* | |
C4B | 0.7304 (4) | 0.49849 (18) | 0.46573 (8) | 0.0749 (7) | |
H4B1 | 0.6331 | 0.4542 | 0.4711 | 0.112* | |
H4B2 | 0.7641 | 0.5330 | 0.5035 | 0.112* | |
H4B3 | 0.8225 | 0.4555 | 0.4531 | 0.112* | |
C5B | 0.46085 (16) | 0.58859 (10) | 0.24468 (6) | 0.0265 (2) | |
C6B | 0.31988 (16) | 0.48480 (10) | 0.18117 (6) | 0.0278 (2) | |
C7B | 0.22910 (18) | 0.40182 (11) | 0.15245 (7) | 0.0351 (3) | |
H7B | 0.2087 | 0.3386 | 0.1727 | 0.042* | |
C8B | 0.1704 (2) | 0.41733 (13) | 0.09242 (7) | 0.0416 (3) | |
H8B | 0.1092 | 0.3634 | 0.0720 | 0.050* | |
C9B | 0.2011 (2) | 0.51220 (14) | 0.06186 (7) | 0.0426 (3) | |
H9B | 0.1617 | 0.5194 | 0.0213 | 0.051* | |
C10B | 0.28859 (19) | 0.59579 (13) | 0.09029 (7) | 0.0385 (3) | |
H10B | 0.3073 | 0.6594 | 0.0701 | 0.046* | |
C11B | 0.34712 (16) | 0.57993 (10) | 0.15049 (6) | 0.0293 (3) |
U11 | U22 | U33 | U12 | U13 | U23 | |
S1A | 0.03615 (17) | 0.02218 (14) | 0.03098 (15) | −0.00052 (11) | −0.00184 (12) | 0.00199 (11) |
O1A | 0.0571 (7) | 0.0297 (5) | 0.0349 (5) | −0.0145 (5) | 0.0114 (5) | 0.0003 (4) |
O2A | 0.0632 (8) | 0.0334 (6) | 0.0590 (7) | −0.0095 (5) | 0.0135 (6) | −0.0154 (5) |
N1A | 0.0299 (5) | 0.0235 (5) | 0.0308 (5) | 0.0027 (4) | 0.0005 (4) | −0.0045 (4) |
N3A | 0.0338 (5) | 0.0207 (5) | 0.0302 (5) | 0.0033 (4) | 0.0004 (4) | −0.0028 (4) |
C1A | 0.0347 (6) | 0.0252 (6) | 0.0302 (6) | −0.0009 (5) | −0.0038 (5) | 0.0009 (5) |
C2A | 0.0305 (6) | 0.0290 (6) | 0.0262 (5) | −0.0016 (5) | 0.0018 (5) | −0.0002 (5) |
C3A | 0.0404 (7) | 0.0466 (8) | 0.0276 (6) | −0.0049 (6) | 0.0021 (5) | 0.0036 (6) |
C4A | 0.0459 (9) | 0.0724 (12) | 0.0423 (9) | 0.0047 (8) | −0.0079 (7) | 0.0156 (8) |
C5A | 0.0252 (5) | 0.0225 (5) | 0.0288 (5) | −0.0017 (4) | 0.0020 (4) | −0.0012 (4) |
C6A | 0.0308 (6) | 0.0232 (5) | 0.0303 (6) | −0.0017 (5) | −0.0008 (5) | −0.0004 (4) |
C7A | 0.0513 (8) | 0.0318 (7) | 0.0306 (6) | −0.0033 (6) | −0.0027 (6) | −0.0028 (5) |
C8A | 0.0571 (10) | 0.0422 (8) | 0.0349 (7) | −0.0071 (7) | −0.0104 (7) | 0.0051 (6) |
C9A | 0.0469 (9) | 0.0373 (8) | 0.0474 (8) | −0.0008 (6) | −0.0128 (7) | 0.0111 (6) |
C10A | 0.0341 (7) | 0.0279 (6) | 0.0470 (8) | 0.0033 (5) | −0.0038 (6) | 0.0043 (6) |
C11A | 0.0259 (5) | 0.0236 (5) | 0.0332 (6) | −0.0013 (4) | −0.0006 (5) | −0.0006 (5) |
S1B | 0.03811 (18) | 0.01909 (14) | 0.03759 (17) | 0.00074 (11) | −0.00421 (13) | −0.00124 (12) |
O1B | 0.0356 (5) | 0.0239 (4) | 0.0418 (5) | 0.0014 (4) | 0.0099 (4) | −0.0031 (4) |
O2B | 0.0559 (7) | 0.0208 (4) | 0.0571 (7) | −0.0054 (4) | 0.0119 (5) | −0.0001 (4) |
N1B | 0.0374 (6) | 0.0219 (5) | 0.0356 (6) | −0.0020 (4) | −0.0004 (5) | 0.0071 (4) |
N3B | 0.0309 (5) | 0.0233 (5) | 0.0306 (5) | −0.0018 (4) | −0.0005 (4) | 0.0046 (4) |
C1B | 0.0316 (6) | 0.0205 (5) | 0.0291 (6) | 0.0003 (4) | −0.0013 (5) | −0.0025 (4) |
C2B | 0.0308 (6) | 0.0234 (5) | 0.0280 (5) | 0.0004 (4) | 0.0021 (5) | −0.0013 (4) |
C3B | 0.0544 (9) | 0.0351 (7) | 0.0311 (7) | 0.0027 (6) | −0.0038 (6) | −0.0079 (6) |
C4B | 0.126 (2) | 0.0584 (12) | 0.0369 (9) | 0.0069 (13) | −0.0219 (11) | −0.0008 (8) |
C5B | 0.0266 (5) | 0.0212 (5) | 0.0317 (6) | 0.0024 (4) | 0.0019 (5) | 0.0022 (4) |
C6B | 0.0266 (6) | 0.0257 (6) | 0.0309 (6) | 0.0015 (4) | 0.0004 (5) | 0.0033 (5) |
C7B | 0.0353 (7) | 0.0304 (6) | 0.0392 (7) | −0.0040 (5) | −0.0017 (5) | 0.0011 (5) |
C8B | 0.0391 (8) | 0.0441 (8) | 0.0408 (8) | −0.0033 (6) | −0.0050 (6) | −0.0045 (6) |
C9B | 0.0396 (8) | 0.0551 (9) | 0.0325 (7) | 0.0016 (7) | −0.0031 (6) | 0.0041 (6) |
C10B | 0.0389 (7) | 0.0419 (8) | 0.0343 (7) | 0.0015 (6) | −0.0012 (6) | 0.0115 (6) |
C11B | 0.0275 (6) | 0.0273 (6) | 0.0329 (6) | 0.0018 (5) | 0.0000 (5) | 0.0057 (5) |
S1A—C5A | 1.7253 (13) | C10A—H10A | 0.9300 |
S1A—C2A | 1.8229 (13) | S1B—C5B | 1.7316 (13) |
O1A—C1A | 1.2971 (17) | S1B—C2B | 1.8136 (13) |
O1A—H1A | 0.8200 | O1B—C1B | 1.2700 (16) |
O2A—C1A | 1.2072 (17) | O2B—C1B | 1.2326 (15) |
N1A—C5A | 1.3396 (16) | N1B—C5B | 1.3560 (16) |
N1A—C11A | 1.3868 (16) | N1B—C11B | 1.3812 (17) |
N1A—H1A1 | 0.8600 | N1B—H1B | 0.8600 |
N3A—C5A | 1.3387 (16) | N3B—C5B | 1.3278 (16) |
N3A—C6A | 1.3922 (16) | N3B—C6B | 1.3990 (16) |
N3A—H3A | 0.8600 | C1B—C2B | 1.5336 (17) |
C1A—C2A | 1.5283 (18) | C2B—C3B | 1.5396 (18) |
C2A—C3A | 1.5366 (18) | C2B—H2B | 0.9800 |
C2A—H2A | 0.9800 | C3B—C4B | 1.520 (2) |
C3A—C4A | 1.521 (2) | C3B—H3B1 | 0.9700 |
C3A—H3A1 | 0.9700 | C3B—H3B2 | 0.9700 |
C3A—H3A2 | 0.9700 | C4B—H4B1 | 0.9600 |
C4A—H4A1 | 0.9600 | C4B—H4B2 | 0.9600 |
C4A—H4A2 | 0.9600 | C4B—H4B3 | 0.9600 |
C4A—H4A3 | 0.9600 | C6B—C7B | 1.3927 (19) |
C6A—C7A | 1.3886 (18) | C6B—C11B | 1.3959 (17) |
C6A—C11A | 1.3937 (18) | C7B—C8B | 1.386 (2) |
C7A—C8A | 1.384 (2) | C7B—H7B | 0.9300 |
C7A—H7A | 0.9300 | C8B—C9B | 1.397 (2) |
C8A—C9A | 1.397 (2) | C8B—H8B | 0.9300 |
C8A—H8A | 0.9300 | C9B—C10B | 1.384 (2) |
C9A—C10A | 1.380 (2) | C9B—H9B | 0.9300 |
C9A—H9A | 0.9300 | C10B—C11B | 1.3898 (18) |
C10A—C11A | 1.3906 (18) | C10B—H10B | 0.9300 |
C5A—S1A—C2A | 101.11 (6) | N1A—C11A—C6A | 107.08 (11) |
C1A—O1A—H1A | 109.5 | C5B—S1B—C2B | 102.31 (6) |
C5A—N1A—C11A | 108.31 (10) | C5B—N1B—C11B | 107.61 (11) |
C5A—N1A—H1A1 | 125.8 | C5B—N1B—H1B | 126.2 |
C11A—N1A—H1A1 | 125.8 | C11B—N1B—H1B | 126.2 |
C5A—N3A—C6A | 108.59 (10) | C5B—N3B—C6B | 105.13 (10) |
C5A—N3A—H3A | 125.7 | O2B—C1B—O1B | 124.44 (12) |
C6A—N3A—H3A | 125.7 | O2B—C1B—C2B | 116.86 (12) |
O2A—C1A—O1A | 125.21 (13) | O1B—C1B—C2B | 118.62 (11) |
O2A—C1A—C2A | 119.41 (13) | C1B—C2B—C3B | 110.76 (11) |
O1A—C1A—C2A | 115.38 (11) | C1B—C2B—S1B | 114.14 (9) |
C1A—C2A—C3A | 110.29 (11) | C3B—C2B—S1B | 104.87 (9) |
C1A—C2A—S1A | 114.11 (9) | C1B—C2B—H2B | 109.0 |
C3A—C2A—S1A | 108.83 (10) | C3B—C2B—H2B | 109.0 |
C1A—C2A—H2A | 107.8 | S1B—C2B—H2B | 109.0 |
C3A—C2A—H2A | 107.8 | C4B—C3B—C2B | 112.86 (13) |
S1A—C2A—H2A | 107.8 | C4B—C3B—H3B1 | 109.0 |
C4A—C3A—C2A | 113.83 (12) | C2B—C3B—H3B1 | 109.0 |
C4A—C3A—H3A1 | 108.8 | C4B—C3B—H3B2 | 109.0 |
C2A—C3A—H3A1 | 108.8 | C2B—C3B—H3B2 | 109.0 |
C4A—C3A—H3A2 | 108.8 | H3B1—C3B—H3B2 | 107.8 |
C2A—C3A—H3A2 | 108.8 | C3B—C4B—H4B1 | 109.5 |
H3A1—C3A—H3A2 | 107.7 | C3B—C4B—H4B2 | 109.5 |
C3A—C4A—H4A1 | 109.5 | H4B1—C4B—H4B2 | 109.5 |
C3A—C4A—H4A2 | 109.5 | C3B—C4B—H4B3 | 109.5 |
H4A1—C4A—H4A2 | 109.5 | H4B1—C4B—H4B3 | 109.5 |
C3A—C4A—H4A3 | 109.5 | H4B2—C4B—H4B3 | 109.5 |
H4A1—C4A—H4A3 | 109.5 | N3B—C5B—N1B | 112.36 (11) |
H4A2—C4A—H4A3 | 109.5 | N3B—C5B—S1B | 127.72 (10) |
N1A—C5A—N3A | 109.77 (11) | N1B—C5B—S1B | 119.92 (10) |
N1A—C5A—S1A | 128.49 (10) | C7B—C6B—C11B | 120.72 (12) |
N3A—C5A—S1A | 121.71 (9) | C7B—C6B—N3B | 129.89 (12) |
N3A—C6A—C7A | 132.35 (12) | C11B—C6B—N3B | 109.39 (11) |
N3A—C6A—C11A | 106.25 (11) | C6B—C7B—C8B | 117.29 (13) |
C7A—C6A—C11A | 121.40 (12) | C6B—C7B—H7B | 121.4 |
C6A—C7A—C8A | 116.31 (14) | C8B—C7B—H7B | 121.4 |
C6A—C7A—H7A | 121.8 | C7B—C8B—C9B | 121.46 (14) |
C8A—C7A—H7A | 121.8 | C7B—C8B—H8B | 119.3 |
C7A—C8A—C9A | 122.16 (14) | C9B—C8B—H8B | 119.3 |
C7A—C8A—H8A | 118.9 | C10B—C9B—C8B | 121.70 (14) |
C9A—C8A—H8A | 118.9 | C10B—C9B—H9B | 119.1 |
C10A—C9A—C8A | 121.69 (14) | C8B—C9B—H9B | 119.1 |
C10A—C9A—H9A | 119.2 | C9B—C10B—C11B | 116.64 (14) |
C8A—C9A—H9A | 119.2 | C9B—C10B—H10B | 121.7 |
C11A—C10A—C9A | 116.22 (14) | C11B—C10B—H10B | 121.7 |
C11A—C10A—H10A | 121.9 | C10B—C11B—N1B | 132.31 (12) |
C9A—C10A—H10A | 121.9 | C10B—C11B—C6B | 122.18 (13) |
C10A—C11A—N1A | 130.69 (12) | N1B—C11B—C6B | 105.51 (11) |
C10A—C11A—C6A | 122.22 (13) | ||
O2A—C1A—C2A—C3A | −59.65 (17) | O2B—C1B—C2B—C3B | 97.98 (15) |
O1A—C1A—C2A—C3A | 119.89 (13) | O1B—C1B—C2B—C3B | −79.02 (15) |
O2A—C1A—C2A—S1A | 177.50 (12) | O2B—C1B—C2B—S1B | −143.95 (11) |
O1A—C1A—C2A—S1A | −2.96 (15) | O1B—C1B—C2B—S1B | 39.04 (15) |
C5A—S1A—C2A—C1A | −66.72 (10) | C5B—S1B—C2B—C1B | 60.70 (10) |
C5A—S1A—C2A—C3A | 169.64 (9) | C5B—S1B—C2B—C3B | −177.92 (9) |
C1A—C2A—C3A—C4A | −58.05 (17) | C1B—C2B—C3B—C4B | −51.59 (19) |
S1A—C2A—C3A—C4A | 67.84 (15) | S1B—C2B—C3B—C4B | −175.17 (15) |
C11A—N1A—C5A—N3A | 0.25 (14) | C6B—N3B—C5B—N1B | −0.25 (14) |
C11A—N1A—C5A—S1A | −177.60 (10) | C6B—N3B—C5B—S1B | −179.87 (10) |
C6A—N3A—C5A—N1A | −0.51 (15) | C11B—N1B—C5B—N3B | 0.49 (15) |
C6A—N3A—C5A—S1A | 177.51 (9) | C11B—N1B—C5B—S1B | −179.86 (9) |
C2A—S1A—C5A—N1A | −11.43 (13) | C2B—S1B—C5B—N3B | 8.10 (13) |
C2A—S1A—C5A—N3A | 170.95 (11) | C2B—S1B—C5B—N1B | −171.50 (10) |
C5A—N3A—C6A—C7A | −179.03 (15) | C5B—N3B—C6B—C7B | −178.77 (14) |
C5A—N3A—C6A—C11A | 0.56 (14) | C5B—N3B—C6B—C11B | −0.08 (14) |
N3A—C6A—C7A—C8A | 179.02 (15) | C11B—C6B—C7B—C8B | 1.0 (2) |
C11A—C6A—C7A—C8A | −0.5 (2) | N3B—C6B—C7B—C8B | 179.62 (14) |
C6A—C7A—C8A—C9A | 0.2 (2) | C6B—C7B—C8B—C9B | 0.1 (2) |
C7A—C8A—C9A—C10A | 0.2 (3) | C7B—C8B—C9B—C10B | −1.2 (3) |
C8A—C9A—C10A—C11A | −0.2 (2) | C8B—C9B—C10B—C11B | 1.1 (2) |
C9A—C10A—C11A—N1A | −178.54 (14) | C9B—C10B—C11B—N1B | 179.59 (14) |
C9A—C10A—C11A—C6A | −0.1 (2) | C9B—C10B—C11B—C6B | 0.0 (2) |
C5A—N1A—C11A—C10A | 178.70 (14) | C5B—N1B—C11B—C10B | 179.90 (15) |
C5A—N1A—C11A—C6A | 0.10 (14) | C5B—N1B—C11B—C6B | −0.50 (14) |
N3A—C6A—C11A—C10A | −179.14 (12) | C7B—C6B—C11B—C10B | −1.2 (2) |
C7A—C6A—C11A—C10A | 0.5 (2) | N3B—C6B—C11B—C10B | −179.99 (13) |
N3A—C6A—C11A—N1A | −0.40 (14) | C7B—C6B—C11B—N1B | 179.20 (12) |
C7A—C6A—C11A—N1A | 179.24 (13) | N3B—C6B—C11B—N1B | 0.36 (14) |
D—H···A | D—H | H···A | D···A | D—H···A |
N1A—H1A1···O1Bi | 0.86 | 1.83 | 2.6574 (14) | 160 |
O1A—H1A···N3B | 0.82 | 1.79 | 2.5757 (14) | 160 |
N1B—H1B···O1Aii | 0.86 | 2.57 | 3.3137 (17) | 145 |
N1B—H1B···O2Bii | 0.86 | 2.16 | 2.8252 (14) | 134 |
N3A—H3A···O1Biii | 0.86 | 1.93 | 2.7658 (14) | 165 |
C2A—H2A···O2Bi | 0.98 | 2.58 | 3.5550 (18) | 172 |
C2B—H2B···O2A | 0.98 | 2.50 | 3.4676 (18) | 170 |
C4A—H4A1···S1A | 0.96 | 2.86 | 3.2565 (18) | 106 |
C7A—H7A···O2Aiv | 0.93 | 2.52 | 3.0843 (19) | 119 |
Symmetry codes: (i) x−1, y, z; (ii) −x+1, y+1/2, −z+1/2; (iii) −x+1, y−1/2, −z+1/2; (iv) −x, y−1/2, −z+1/2. |
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