Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S160053680605402X/wk2037sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S160053680605402X/wk2037Isup2.hkl |
CCDC reference: 634067
Key indicators
- Single-crystal X-ray study
- T = 113 K
- Mean (C-C) = 0.005 Å
- R factor = 0.044
- wR factor = 0.122
- Data-to-parameter ratio = 16.4
checkCIF/PLATON results
No syntax errors found
Alert level B PLAT148_ALERT_3_B su on the c - Axis is Too Large (x 1000) . 50 Ang.
Alert level C PLAT066_ALERT_1_C Predicted and Reported Transmissions Identical . ? PLAT180_ALERT_3_C Check Cell Rounding: # of Values Ending with 0 = 3 PLAT230_ALERT_2_C Hirshfeld Test Diff for O5 - N1 .. 6.36 su PLAT230_ALERT_2_C Hirshfeld Test Diff for O12 - N2 .. 6.03 su PLAT340_ALERT_3_C Low Bond Precision on C-C bonds (x 1000) Ang ... 5 PLAT731_ALERT_1_C Bond Calc 1.412(4), Rep 1.4122(16) ...... 2.50 su-Ra S1 -O3 1.555 1.555 PLAT731_ALERT_1_C Bond Calc 1.744(5), Rep 1.744(2) ...... 2.50 su-Ra S1 -C7 1.555 1.555 PLAT731_ALERT_1_C Bond Calc 1.604(5), Rep 1.6040(15) ...... 3.33 su-Ra S2 -O8 1.555 1.555 PLAT731_ALERT_1_C Bond Calc 1.742(5), Rep 1.742(2) ...... 2.50 su-Ra S2 -C19 1.555 1.555 PLAT737_ALERT_1_C D...A Calc 2.586(7), Rep 2.586(2) ...... 3.50 su-Ra O7 -O11 1.555 1.555
Alert level G HYDTR01_ALERT_1_G Extra text has been found in the _refine_ls_hydrogen_treatment fi Explanatory text should be in the _publ_section_refinement field. Hydrogen treatment given as constr, OH refxyz Hydrogen treatment identified as refxyz
0 ALERT level A = In general: serious problem 1 ALERT level B = Potentially serious problem 10 ALERT level C = Check and explain 1 ALERT level G = General alerts; check 7 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 3 ALERT type 3 Indicator that the structure quality may be low 0 ALERT type 4 Improvement, methodology, query or suggestion 0 ALERT type 5 Informative message, check
Data collection: CrystalClear (Rigaku, 1999); cell refinement: CrystalClear; data reduction: CrystalClear; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXS97 (Sheldrick, 1997); molecular graphics: CrystalStructure (Rigaku/MSC, 2004); software used to prepare material for publication: CrystalStructure.
C12H9NO6S | Z = 4 |
Mr = 295.27 | F(000) = 608 |
Triclinic, P1 | Dx = 1.543 Mg m−3 |
Hall symbol: -P 1 | Melting point: 352 K |
a = 8.390 (2) Å | Mo Kα radiation, λ = 0.71070 Å |
b = 8.594 (3) Å | Cell parameters from 2407 reflections |
c = 18.36 (5) Å | θ = 2.3–28.1° |
α = 76.888 (8)° | µ = 0.28 mm−1 |
β = 80.400 (8)° | T = 113 K |
γ = 89.340 (9)° | Prism, colourless |
V = 1271 (4) Å3 | 0.26 × 0.22 × 0.20 mm |
Rigaku Saturn diffractometer | 6064 independent reflections |
Radiation source: rotating anode | 3572 reflections with I > 2σ(I) |
Confocal monochromator | Rint = 0.032 |
Detector resolution: 7.31 pixels mm-1 | θmax = 27.9°, θmin = 2.3° |
ω scans | h = −10→11 |
Absorption correction: multi-scan (SADABS; Sheldrick, 1996) | k = −11→11 |
Tmin = 0.930, Tmax = 0.946 | l = −24→24 |
11922 measured reflections |
Refinement on F2 | Secondary atom site location: difference Fourier map |
Least-squares matrix: full | Hydrogen site location: geom, OH difmap |
R[F2 > 2σ(F2)] = 0.044 | H atoms treated by a mixture of independent and constrained refinement |
wR(F2) = 0.122 | w = 1/[σ2(Fo2) + (0.0633P)2] where P = (Fo2 + 2Fc2)/3 |
S = 0.97 | (Δ/σ)max < 0.001 |
6064 reflections | Δρmax = 0.20 e Å−3 |
369 parameters | Δρmin = −0.28 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: 0.031 (3) |
Experimental. Spectroscopic analysis: IR (KBr, ν, cm-1): 3260, 1621, 1535, 1194, 973. Analysis required for C12H9NO6S: C 48.81; H 3.07; N 4.74%. Found: C 48.81; H 3.14; N 4.70%. |
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 | ||
S1 | 0.17914 (7) | 0.73284 (6) | 0.38492 (3) | 0.05564 (19) | |
S2 | 0.89507 (7) | 0.23109 (6) | 0.14009 (3) | 0.05648 (19) | |
O1 | 0.0900 (2) | 0.8479 (2) | 0.09128 (9) | 0.0738 (5) | |
H1 | 0.117 (4) | 0.912 (4) | 0.0455 (17) | 0.111* | |
O2 | 0.32403 (17) | 0.74718 (17) | 0.31415 (8) | 0.0591 (4) | |
O3 | 0.03396 (19) | 0.69101 (19) | 0.36378 (9) | 0.0691 (4) | |
O4 | 0.2436 (2) | 0.62845 (19) | 0.44335 (9) | 0.0835 (5) | |
O5 | 0.2272 (2) | 1.0796 (2) | −0.01775 (9) | 0.0782 (5) | |
O6 | 0.4432 (2) | 1.1983 (2) | −0.00761 (10) | 0.0827 (5) | |
O7 | 0.6348 (2) | 0.35887 (19) | 0.40862 (9) | 0.0725 (5) | |
H7 | 0.635 (4) | 0.431 (4) | 0.4329 (16) | 0.109* | |
O8 | 0.76360 (16) | 0.36660 (16) | 0.14605 (7) | 0.0542 (4) | |
O9 | 0.8623 (2) | 0.10686 (17) | 0.20670 (9) | 0.0754 (5) | |
O10 | 0.8865 (2) | 0.2010 (2) | 0.06813 (9) | 0.0820 (5) | |
O11 | 0.6345 (2) | 0.6360 (2) | 0.44145 (9) | 0.0734 (5) | |
O12 | 0.67806 (19) | 0.85269 (18) | 0.35370 (9) | 0.0669 (4) | |
N1 | 0.3309 (2) | 1.1025 (2) | 0.01874 (10) | 0.0580 (5) | |
N2 | 0.6692 (2) | 0.7066 (2) | 0.37394 (10) | 0.0534 (4) | |
C1 | 0.2014 (2) | 0.8923 (2) | 0.12769 (11) | 0.0503 (5) | |
C2 | 0.2002 (2) | 0.8063 (2) | 0.20221 (11) | 0.0499 (5) | |
H2 | 0.1231 | 0.7252 | 0.2246 | 0.060* | |
C3 | 0.3132 (2) | 0.8427 (2) | 0.24161 (11) | 0.0477 (5) | |
C4 | 0.4292 (3) | 0.9624 (3) | 0.21154 (13) | 0.0604 (6) | |
H4 | 0.5036 | 0.9855 | 0.2402 | 0.073* | |
C5 | 0.4323 (3) | 1.0462 (3) | 0.13877 (13) | 0.0597 (6) | |
H5 | 0.5104 | 1.1267 | 0.1171 | 0.072* | |
C6 | 0.3199 (2) | 1.0122 (2) | 0.09689 (11) | 0.0479 (5) | |
C7 | 0.1697 (3) | 0.9261 (2) | 0.40014 (10) | 0.0506 (5) | |
C8 | 0.0311 (3) | 1.0115 (3) | 0.39239 (11) | 0.0618 (6) | |
H8 | −0.0558 | 0.9693 | 0.3770 | 0.074* | |
C9 | 0.0247 (4) | 1.1619 (3) | 0.40814 (13) | 0.0820 (8) | |
H9 | −0.0676 | 1.2219 | 0.4036 | 0.098* | |
C10 | 0.1549 (5) | 1.2222 (3) | 0.43047 (15) | 0.0945 (10) | |
H10 | 0.1497 | 1.3233 | 0.4409 | 0.113* | |
C11 | 0.2912 (4) | 1.1368 (4) | 0.43755 (17) | 0.0970 (10) | |
H11 | 0.3782 | 1.1798 | 0.4525 | 0.116* | |
C12 | 0.3005 (3) | 0.9867 (3) | 0.42254 (14) | 0.0742 (7) | |
H12 | 0.3930 | 0.9273 | 0.4274 | 0.089* | |
C13 | 0.6770 (2) | 0.4465 (2) | 0.33739 (11) | 0.0466 (5) | |
C14 | 0.6981 (2) | 0.3634 (2) | 0.27965 (11) | 0.0489 (5) | |
H14 | 0.6794 | 0.2534 | 0.2910 | 0.059* | |
C15 | 0.7466 (2) | 0.4450 (2) | 0.20628 (10) | 0.0438 (4) | |
C16 | 0.7738 (2) | 0.6089 (2) | 0.18622 (12) | 0.0526 (5) | |
H16 | 0.8080 | 0.6613 | 0.1359 | 0.063* | |
C17 | 0.7489 (2) | 0.6917 (2) | 0.24235 (11) | 0.0503 (5) | |
H17 | 0.7657 | 0.8020 | 0.2302 | 0.060* | |
C18 | 0.6991 (2) | 0.6127 (2) | 0.31709 (11) | 0.0430 (4) | |
C19 | 1.0767 (2) | 0.3292 (2) | 0.13836 (11) | 0.0488 (5) | |
C20 | 1.1399 (3) | 0.3156 (3) | 0.20430 (13) | 0.0647 (6) | |
H20 | 1.0877 | 0.2525 | 0.2499 | 0.078* | |
C21 | 1.2829 (3) | 0.3981 (3) | 0.20088 (17) | 0.0834 (8) | |
H21 | 1.3276 | 0.3902 | 0.2446 | 0.100* | |
C22 | 1.3590 (3) | 0.4917 (3) | 0.13319 (19) | 0.0857 (8) | |
H22 | 1.4545 | 0.5472 | 0.1315 | 0.103* | |
C23 | 1.2954 (3) | 0.5038 (3) | 0.06862 (17) | 0.0801 (8) | |
H23 | 1.3481 | 0.5671 | 0.0232 | 0.096* | |
C24 | 1.1545 (3) | 0.4234 (3) | 0.07010 (13) | 0.0616 (6) | |
H24 | 1.1113 | 0.4318 | 0.0259 | 0.074* |
U11 | U22 | U33 | U12 | U13 | U23 | |
S1 | 0.0716 (4) | 0.0514 (3) | 0.0467 (3) | −0.0005 (3) | −0.0188 (3) | −0.0103 (2) |
S2 | 0.0728 (4) | 0.0465 (3) | 0.0513 (3) | −0.0061 (3) | −0.0016 (3) | −0.0197 (2) |
O1 | 0.0827 (12) | 0.0825 (12) | 0.0563 (10) | −0.0270 (9) | −0.0297 (9) | −0.0015 (8) |
O2 | 0.0635 (9) | 0.0669 (9) | 0.0536 (9) | 0.0197 (7) | −0.0224 (7) | −0.0192 (7) |
O3 | 0.0729 (11) | 0.0721 (10) | 0.0664 (10) | −0.0203 (8) | −0.0156 (8) | −0.0205 (8) |
O4 | 0.1270 (15) | 0.0649 (10) | 0.0609 (10) | 0.0134 (10) | −0.0404 (10) | −0.0018 (8) |
O5 | 0.0974 (13) | 0.0777 (11) | 0.0572 (10) | −0.0108 (10) | −0.0247 (10) | −0.0016 (9) |
O6 | 0.0912 (13) | 0.0690 (11) | 0.0756 (12) | −0.0220 (10) | 0.0103 (10) | −0.0074 (9) |
O7 | 0.1100 (14) | 0.0566 (10) | 0.0444 (9) | −0.0122 (9) | 0.0040 (9) | −0.0100 (7) |
O8 | 0.0556 (8) | 0.0663 (9) | 0.0467 (8) | 0.0014 (7) | −0.0122 (7) | −0.0227 (7) |
O9 | 0.1015 (13) | 0.0437 (8) | 0.0695 (11) | −0.0120 (8) | 0.0090 (9) | −0.0053 (8) |
O10 | 0.1079 (14) | 0.0846 (12) | 0.0649 (11) | −0.0094 (10) | −0.0069 (10) | −0.0457 (9) |
O11 | 0.0960 (13) | 0.0765 (11) | 0.0511 (10) | 0.0051 (9) | −0.0071 (9) | −0.0258 (8) |
O12 | 0.0745 (11) | 0.0502 (9) | 0.0844 (11) | 0.0054 (8) | −0.0196 (9) | −0.0281 (8) |
N1 | 0.0714 (13) | 0.0452 (10) | 0.0555 (11) | 0.0039 (9) | 0.0007 (10) | −0.0156 (9) |
N2 | 0.0466 (10) | 0.0602 (11) | 0.0599 (12) | 0.0045 (8) | −0.0128 (8) | −0.0246 (9) |
C1 | 0.0526 (12) | 0.0516 (12) | 0.0507 (12) | 0.0005 (9) | −0.0131 (10) | −0.0164 (9) |
C2 | 0.0523 (12) | 0.0510 (11) | 0.0482 (11) | −0.0022 (9) | −0.0121 (9) | −0.0119 (9) |
C3 | 0.0502 (12) | 0.0501 (11) | 0.0478 (11) | 0.0124 (9) | −0.0128 (9) | −0.0187 (9) |
C4 | 0.0556 (13) | 0.0673 (14) | 0.0671 (15) | 0.0004 (11) | −0.0174 (11) | −0.0281 (12) |
C5 | 0.0540 (13) | 0.0571 (13) | 0.0705 (15) | −0.0044 (10) | −0.0059 (11) | −0.0228 (11) |
C6 | 0.0519 (12) | 0.0456 (11) | 0.0483 (12) | 0.0045 (9) | −0.0054 (9) | −0.0175 (9) |
C7 | 0.0576 (13) | 0.0552 (12) | 0.0387 (11) | −0.0054 (10) | −0.0056 (9) | −0.0117 (9) |
C8 | 0.0731 (16) | 0.0624 (14) | 0.0486 (12) | 0.0058 (12) | −0.0148 (11) | −0.0070 (10) |
C9 | 0.123 (2) | 0.0654 (16) | 0.0544 (15) | 0.0262 (16) | −0.0112 (15) | −0.0102 (12) |
C10 | 0.157 (3) | 0.0552 (15) | 0.0666 (18) | −0.0163 (19) | 0.0094 (19) | −0.0233 (13) |
C11 | 0.100 (2) | 0.104 (2) | 0.097 (2) | −0.034 (2) | 0.0092 (18) | −0.0616 (19) |
C12 | 0.0602 (15) | 0.0955 (19) | 0.0784 (17) | −0.0089 (13) | −0.0063 (13) | −0.0472 (15) |
C13 | 0.0469 (11) | 0.0503 (11) | 0.0405 (11) | −0.0029 (9) | −0.0031 (9) | −0.0088 (9) |
C14 | 0.0549 (12) | 0.0430 (10) | 0.0481 (11) | −0.0059 (9) | −0.0050 (9) | −0.0115 (9) |
C15 | 0.0403 (10) | 0.0524 (11) | 0.0422 (11) | −0.0003 (8) | −0.0086 (8) | −0.0164 (9) |
C16 | 0.0554 (13) | 0.0550 (12) | 0.0450 (11) | −0.0020 (10) | −0.0071 (10) | −0.0071 (10) |
C17 | 0.0528 (12) | 0.0422 (10) | 0.0542 (12) | −0.0013 (9) | −0.0081 (10) | −0.0082 (9) |
C18 | 0.0379 (10) | 0.0461 (10) | 0.0495 (11) | 0.0008 (8) | −0.0100 (9) | −0.0182 (9) |
C19 | 0.0555 (12) | 0.0409 (10) | 0.0469 (11) | 0.0094 (9) | −0.0015 (9) | −0.0093 (9) |
C20 | 0.0690 (16) | 0.0696 (15) | 0.0556 (13) | 0.0119 (12) | −0.0122 (12) | −0.0136 (11) |
C21 | 0.0721 (18) | 0.093 (2) | 0.095 (2) | 0.0164 (15) | −0.0352 (16) | −0.0281 (17) |
C22 | 0.0552 (16) | 0.0751 (18) | 0.124 (3) | 0.0042 (13) | −0.0136 (17) | −0.0190 (18) |
C23 | 0.0572 (16) | 0.0711 (16) | 0.096 (2) | 0.0019 (13) | 0.0038 (14) | 0.0023 (14) |
C24 | 0.0631 (15) | 0.0580 (13) | 0.0566 (13) | 0.0080 (11) | −0.0043 (11) | −0.0028 (11) |
S1—O4 | 1.412 (3) | C7—C12 | 1.380 (3) |
S1—O3 | 1.4122 (16) | C8—C9 | 1.386 (3) |
S1—O2 | 1.608 (3) | C8—H8 | 0.9300 |
S1—C7 | 1.744 (2) | C9—C10 | 1.374 (4) |
S2—O10 | 1.416 (4) | C9—H9 | 0.9300 |
S2—O9 | 1.419 (3) | C10—C11 | 1.361 (4) |
S2—O8 | 1.6040 (15) | C10—H10 | 0.9300 |
S2—C19 | 1.742 (2) | C11—C12 | 1.377 (4) |
O1—C1 | 1.341 (3) | C11—H11 | 0.9300 |
O1—H1 | 0.89 (3) | C12—H12 | 0.9300 |
O2—C3 | 1.414 (4) | C13—C14 | 1.394 (4) |
O5—N1 | 1.226 (3) | C13—C18 | 1.398 (3) |
O6—N1 | 1.219 (2) | C14—C15 | 1.366 (4) |
O7—C13 | 1.345 (4) | C14—H14 | 0.9300 |
O7—H7 | 0.84 (3) | C15—C16 | 1.384 (3) |
O8—C15 | 1.407 (4) | C16—C17 | 1.367 (4) |
O11—N2 | 1.238 (4) | C16—H16 | 0.9300 |
O12—N2 | 1.225 (2) | C17—C18 | 1.383 (4) |
N1—C6 | 1.457 (4) | C17—H17 | 0.9300 |
N2—C18 | 1.447 (3) | C19—C20 | 1.382 (4) |
C1—C6 | 1.393 (3) | C19—C24 | 1.390 (4) |
C1—C2 | 1.398 (4) | C20—C21 | 1.385 (3) |
C2—C3 | 1.363 (3) | C20—H20 | 0.9300 |
C2—H2 | 0.9300 | C21—C22 | 1.376 (5) |
C3—C4 | 1.377 (3) | C21—H21 | 0.9300 |
C4—C5 | 1.363 (4) | C22—C23 | 1.362 (5) |
C4—H4 | 0.9300 | C22—H22 | 0.9300 |
C5—C6 | 1.384 (3) | C23—C24 | 1.369 (3) |
C5—H5 | 0.9300 | C23—H23 | 0.9300 |
C7—C8 | 1.378 (3) | C24—H24 | 0.9300 |
O4—S1—O3 | 120.22 (11) | C10—C9—H9 | 120.1 |
O4—S1—O2 | 101.80 (17) | C8—C9—H9 | 120.1 |
O3—S1—O2 | 109.21 (16) | C11—C10—C9 | 121.2 (3) |
O4—S1—C7 | 110.51 (14) | C11—C10—H10 | 119.4 |
O3—S1—C7 | 110.25 (10) | C9—C10—H10 | 119.4 |
O2—S1—C7 | 103.18 (10) | C10—C11—C12 | 120.1 (3) |
O10—S2—O9 | 120.65 (17) | C10—C11—H11 | 120.0 |
O10—S2—O8 | 102.16 (9) | C12—C11—H11 | 120.0 |
O9—S2—O8 | 108.71 (11) | C11—C12—C7 | 118.7 (3) |
O10—S2—C19 | 110.82 (10) | C11—C12—H12 | 120.6 |
O9—S2—C19 | 109.51 (12) | C7—C12—H12 | 120.6 |
O8—S2—C19 | 103.36 (8) | O7—C13—C14 | 116.6 (2) |
C1—O1—H1 | 101.1 (19) | O7—C13—C18 | 125.31 (19) |
C3—O2—S1 | 121.95 (17) | C14—C13—C18 | 118.1 (2) |
C13—O7—H7 | 100 (2) | C15—C14—C13 | 119.4 (2) |
C15—O8—S2 | 120.80 (12) | C15—C14—H14 | 120.3 |
O6—N1—O5 | 122.7 (2) | C13—C14—H14 | 120.3 |
O6—N1—C6 | 118.4 (2) | C14—C15—C16 | 122.64 (19) |
O5—N1—C6 | 119.0 (2) | C14—C15—O8 | 121.2 (2) |
O12—N2—O11 | 122.31 (18) | C16—C15—O8 | 116.1 (2) |
O12—N2—C18 | 119.1 (2) | C17—C16—C15 | 118.2 (2) |
O11—N2—C18 | 118.6 (2) | C17—C16—H16 | 120.9 |
O1—C1—C6 | 125.7 (2) | C15—C16—H16 | 120.9 |
O1—C1—C2 | 116.4 (2) | C16—C17—C18 | 120.5 (2) |
C6—C1—C2 | 117.92 (18) | C16—C17—H17 | 119.8 |
C3—C2—C1 | 119.3 (2) | C18—C17—H17 | 119.8 |
C3—C2—H2 | 120.4 | C17—C18—C13 | 121.05 (18) |
C1—C2—H2 | 120.4 | C17—C18—N2 | 118.3 (2) |
C2—C3—C4 | 122.9 (2) | C13—C18—N2 | 120.7 (2) |
C2—C3—O2 | 120.1 (2) | C20—C19—C24 | 120.9 (2) |
C4—C3—O2 | 116.79 (18) | C20—C19—S2 | 120.22 (17) |
C5—C4—C3 | 118.3 (2) | C24—C19—S2 | 118.92 (19) |
C5—C4—H4 | 120.8 | C19—C20—C21 | 118.5 (2) |
C3—C4—H4 | 120.8 | C19—C20—H20 | 120.8 |
C4—C5—C6 | 120.4 (2) | C21—C20—H20 | 120.8 |
C4—C5—H5 | 119.8 | C22—C21—C20 | 120.4 (3) |
C6—C5—H5 | 119.8 | C22—C21—H21 | 119.8 |
C5—C6—C1 | 121.2 (2) | C20—C21—H21 | 119.8 |
C5—C6—N1 | 118.3 (2) | C23—C22—C21 | 120.5 (3) |
C1—C6—N1 | 120.55 (18) | C23—C22—H22 | 119.8 |
C8—C7—C12 | 121.8 (2) | C21—C22—H22 | 119.8 |
C8—C7—S1 | 119.65 (17) | C22—C23—C24 | 120.5 (3) |
C12—C7—S1 | 118.47 (18) | C22—C23—H23 | 119.7 |
C7—C8—C9 | 118.3 (2) | C24—C23—H23 | 119.7 |
C7—C8—H8 | 120.9 | C23—C24—C19 | 119.3 (2) |
C9—C8—H8 | 120.9 | C23—C24—H24 | 120.4 |
C10—C9—C8 | 119.9 (3) | C19—C24—H24 | 120.4 |
O4—S1—O2—C3 | −179.76 (15) | C10—C11—C12—C7 | 0.2 (4) |
O3—S1—O2—C3 | 52.13 (18) | C8—C7—C12—C11 | 0.1 (4) |
C7—S1—O2—C3 | −65.14 (17) | S1—C7—C12—C11 | −177.5 (2) |
O10—S2—O8—C15 | −172.53 (14) | O7—C13—C14—C15 | −177.69 (18) |
O9—S2—O8—C15 | 58.9 (2) | C18—C13—C14—C15 | 3.0 (3) |
C19—S2—O8—C15 | −57.38 (16) | C13—C14—C15—C16 | −1.0 (3) |
O1—C1—C2—C3 | 178.21 (19) | C13—C14—C15—O8 | −177.63 (16) |
C6—C1—C2—C3 | 0.2 (3) | S2—O8—C15—C14 | −63.6 (2) |
C1—C2—C3—C4 | 0.6 (3) | S2—O8—C15—C16 | 119.50 (17) |
C1—C2—C3—O2 | −173.78 (17) | C14—C15—C16—C17 | −0.8 (3) |
S1—O2—C3—C2 | −63.9 (2) | O8—C15—C16—C17 | 176.02 (17) |
S1—O2—C3—C4 | 121.37 (18) | C15—C16—C17—C18 | 0.5 (3) |
C2—C3—C4—C5 | −1.1 (3) | C16—C17—C18—C13 | 1.6 (3) |
O2—C3—C4—C5 | 173.47 (18) | C16—C17—C18—N2 | −177.88 (17) |
C3—C4—C5—C6 | 0.8 (3) | O7—C13—C18—C17 | 177.38 (19) |
C4—C5—C6—C1 | 0.0 (3) | C14—C13—C18—C17 | −3.4 (3) |
C4—C5—C6—N1 | −178.49 (19) | O7—C13—C18—N2 | −3.1 (3) |
O1—C1—C6—C5 | −178.3 (2) | C14—C13—C18—N2 | 176.16 (17) |
C2—C1—C6—C5 | −0.4 (3) | O12—N2—C18—C17 | 4.9 (3) |
O1—C1—C6—N1 | 0.1 (3) | O11—N2—C18—C17 | −175.51 (17) |
C2—C1—C6—N1 | 177.96 (17) | O12—N2—C18—C13 | −174.60 (17) |
O6—N1—C6—C5 | 3.6 (3) | O11—N2—C18—C13 | 5.0 (3) |
O5—N1—C6—C5 | −176.22 (19) | O10—S2—C19—C20 | −154.48 (18) |
O6—N1—C6—C1 | −174.83 (19) | O9—S2—C19—C20 | −19.0 (2) |
O5—N1—C6—C1 | 5.3 (3) | O8—S2—C19—C20 | 96.73 (18) |
O4—S1—C7—C8 | −133.95 (18) | O10—S2—C19—C24 | 26.8 (2) |
O3—S1—C7—C8 | 1.4 (2) | O9—S2—C19—C24 | 162.29 (16) |
O2—S1—C7—C8 | 117.9 (2) | O8—S2—C19—C24 | −81.99 (18) |
O4—S1—C7—C12 | 43.6 (2) | C24—C19—C20—C21 | 0.0 (3) |
O3—S1—C7—C12 | 178.95 (17) | S2—C19—C20—C21 | −178.69 (18) |
O2—S1—C7—C12 | −64.5 (2) | C19—C20—C21—C22 | 0.3 (4) |
C12—C7—C8—C9 | −0.3 (3) | C20—C21—C22—C23 | −0.4 (4) |
S1—C7—C8—C9 | 177.17 (16) | C21—C22—C23—C24 | 0.2 (4) |
C7—C8—C9—C10 | 0.3 (4) | C22—C23—C24—C19 | 0.0 (4) |
C8—C9—C10—C11 | 0.0 (4) | C20—C19—C24—C23 | −0.2 (3) |
C9—C10—C11—C12 | −0.2 (5) | S2—C19—C24—C23 | 178.56 (18) |
D—H···A | D—H | H···A | D···A | D—H···A |
O1—H1···O5 | 0.89 (3) | 1.79 (3) | 2.602 (4) | 151 (3) |
O7—H7···O11 | 0.84 (3) | 1.80 (3) | 2.586 (2) | 154 (3) |