Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S160053680602650X/sg2048sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S160053680602650X/sg2048Isup2.hkl |
CCDC reference: 618331
Key indicators
- Single-crystal X-ray study
- T = 291 K
- Mean (C-C) = 0.005 Å
- R factor = 0.042
- wR factor = 0.113
- Data-to-parameter ratio = 14.6
checkCIF/PLATON results
No syntax errors found
Alert level B PLAT417_ALERT_2_B Short Inter D-H..H-D H0A .. H2N .. 2.07 Ang.
Alert level C PLAT042_ALERT_1_C Calc. and Rep. MoietyFormula Strings Differ .... ? PLAT062_ALERT_4_C Rescale T(min) & T(max) by ..................... 0.95 PLAT220_ALERT_2_C Large Non-Solvent C Ueq(max)/Ueq(min) ... 3.19 Ratio PLAT222_ALERT_3_C Large Non-Solvent H Ueq(max)/Ueq(min) ... 3.33 Ratio PLAT242_ALERT_2_C Check Low Ueq as Compared to Neighbors for S2 PLAT340_ALERT_3_C Low Bond Precision on C-C bonds (x 1000) Ang ... 5 PLAT720_ALERT_4_C Number of Unusual/Non-Standard Label(s) ........ 2 PLAT731_ALERT_1_C Bond Calc 0.82(4), Rep 0.823(10) ...... 4.00 su-Rat O8 -H0A 1.555 1.555 PLAT731_ALERT_1_C Bond Calc 0.82(4), Rep 0.829(10) ...... 4.00 su-Rat O8 -H0B 1.555 1.555 PLAT732_ALERT_1_C Angle Calc 108(4), Rep 108.0(17) ...... 2.35 su-Rat H0A -O8 -H0B 1.555 1.555 1.555 PLAT735_ALERT_1_C D-H Calc 0.82(4), Rep 0.823(10) ...... 4.00 su-Rat O8 -H1# 1.555 1.555 PLAT735_ALERT_1_C D-H Calc 0.82(4), Rep 0.829(10) ...... 4.00 su-Rat O8 -H2# 1.555 1.555 PLAT736_ALERT_1_C H...A Calc 1.91(4), Rep 1.908(10) ...... 4.00 su-Rat H1# -O4 1.555 1.555 PLAT736_ALERT_1_C H...A Calc 1.99(4), Rep 1.983(10) ...... 4.00 su-Rat H2# -O5 1.555 1.554
Alert level G ABSTM02_ALERT_3_G When printed, the submitted absorption T values will be replaced by the scaled T values. Since the ratio of scaled T's is identical to the ratio of reported T values, the scaling does not imply a change to the absorption corrections used in the study. Ratio of Tmax expected/reported 0.949 Tmax scaled 0.943 Tmin scaled 0.884 REFLT03_ALERT_4_G Please check that the estimate of the number of Friedel pairs is correct. If it is not, please give the correct count in the _publ_section_exptl_refinement section of the submitted CIF. From the CIF: _diffrn_reflns_theta_max 26.00 From the CIF: _reflns_number_total 6202 Count of symmetry unique reflns 3101 Completeness (_total/calc) 200.00% TEST3: Check Friedels for noncentro structure Estimate of Friedel pairs measured 3101 Fraction of Friedel pairs measured 1.000 Are heavy atom types Z>Si present yes
0 ALERT level A = In general: serious problem 1 ALERT level B = Potentially serious problem 14 ALERT level C = Check and explain 2 ALERT level G = General alerts; check 8 ALERT type 1 CIF construction/syntax error, inconsistent or missing data 3 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 3 ALERT type 4 Improvement, methodology, query or suggestion
Data collection: XSCANS (Siemens, 1994); cell refinement: XSCANS; data reduction: SHELXTL (Bruker, 1998); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL.
C19H24N2O2+·2C7H7SO3−·H2O | Z = 1 |
Mr = 656.81 | F(000) = 348 |
Triclinic, P1 | Dx = 1.380 Mg m−3 |
Hall symbol: P1 | Mo Kα radiation, λ = 0.71073 Å |
a = 6.565 (3) Å | Cell parameters from 43 reflections |
b = 9.599 (4) Å | θ = 4.0–15.3° |
c = 12.748 (5) Å | µ = 0.22 mm−1 |
α = 85.25 (3)° | T = 291 K |
β = 84.08 (3)° | Block, colorless |
γ = 82.71 (3)° | 0.54 × 0.42 × 0.26 mm |
V = 790.6 (6) Å3 |
Siemens P4 diffractometer | 5316 reflections with I > 2σ(I) |
Radiation source: normal-focus sealed tube | Rint = 0.000 |
Graphite monochromator | θmax = 26.0°, θmin = 1.6° |
ω scans | h = −8→8 |
Absorption correction: ψ scan (XSCANS; Siemens, 1994) | k = −11→11 |
Tmin = 0.932, Tmax = 0.994 | l = −15→15 |
6402 measured reflections | 3 standard reflections every 97 reflections |
6202 independent reflections | intensity decay: 4.9% |
Refinement on F2 | Hydrogen site location: inferred from neighbouring sites |
Least-squares matrix: full | H atoms treated by a mixture of independent and constrained refinement |
R[F2 > 2σ(F2)] = 0.042 | w = 1/[σ2(Fo2) + (0.066P)2 + 0.0459P] where P = (Fo2 + 2Fc2)/3 |
wR(F2) = 0.113 | (Δ/σ)max = 0.001 |
S = 1.05 | Δρmax = 0.26 e Å−3 |
6198 reflections | Δρmin = −0.39 e Å−3 |
425 parameters | Extinction correction: SHELXL97, Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4 |
6 restraints | Extinction coefficient: 0.016 (3) |
Primary atom site location: structure-invariant direct methods | Absolute structure: Flack (1983), 2176 Friedel pairs |
Secondary atom site location: difference Fourier map | Absolute structure parameter: −0.03 (6) |
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 | 0.47843 (10) | 0.26388 (7) | 0.35937 (6) | 0.03814 (19) | |
S2 | 0.17446 (11) | 0.63415 (8) | 0.98141 (7) | 0.0428 (2) | |
O1 | 1.1353 (3) | 0.8071 (2) | 0.23113 (19) | 0.0450 (5) | |
H1O | 1.2057 | 0.7849 | 0.1767 | 0.054* | |
O2 | 0.6877 (4) | 0.2786 (3) | 0.3761 (2) | 0.0601 (7) | |
O3 | 0.4482 (4) | 0.1270 (2) | 0.3299 (2) | 0.0494 (6) | |
O4 | 0.3874 (4) | 0.3755 (3) | 0.28757 (19) | 0.0517 (6) | |
O5 | 0.2942 (3) | 0.7194 (2) | 1.03578 (18) | 0.0471 (6) | |
O6 | 0.0486 (4) | 0.5535 (3) | 1.0580 (3) | 0.0736 (9) | |
O7 | 0.3024 (5) | 0.5566 (3) | 0.9030 (2) | 0.0764 (9) | |
N1 | 0.9053 (4) | 1.2983 (3) | 0.1145 (2) | 0.0421 (6) | |
N2 | 0.7345 (4) | 0.6850 (2) | 0.3182 (2) | 0.0366 (6) | |
C1 | 0.7592 (5) | 1.2270 (3) | 0.0800 (2) | 0.0345 (6) | |
C2 | 0.6122 (6) | 1.2972 (4) | 0.0166 (3) | 0.0469 (8) | |
H2 | 0.6140 | 1.3923 | −0.0040 | 0.056* | |
C3 | 0.4670 (6) | 1.2255 (4) | −0.0147 (3) | 0.0506 (9) | |
H3 | 0.3670 | 1.2722 | −0.0559 | 0.061* | |
C4 | 0.4661 (5) | 1.0809 (4) | 0.0147 (3) | 0.0478 (8) | |
H4 | 0.3658 | 1.0327 | −0.0074 | 0.057* | |
C5 | 0.6090 (5) | 1.0119 (3) | 0.0746 (2) | 0.0372 (7) | |
H5 | 0.6059 | 0.9163 | 0.0929 | 0.045* | |
C6 | 0.7638 (5) | 1.0808 (3) | 0.1106 (2) | 0.0311 (6) | |
C7 | 0.9193 (4) | 1.0165 (3) | 0.1744 (2) | 0.0326 (6) | |
C8 | 1.0588 (5) | 1.0960 (3) | 0.2049 (2) | 0.0391 (7) | |
H8 | 1.1616 | 1.0544 | 0.2464 | 0.047* | |
C9 | 1.0472 (5) | 1.2383 (3) | 0.1742 (3) | 0.0437 (8) | |
H9 | 1.1412 | 1.2919 | 0.1962 | 0.052* | |
C10 | 0.9337 (4) | 0.8606 (3) | 0.2070 (2) | 0.0336 (6) | |
H10 | 0.8985 | 0.8110 | 0.1485 | 0.040* | |
C11 | 0.7770 (4) | 0.8366 (3) | 0.3034 (2) | 0.0302 (6) | |
H11 | 0.6471 | 0.8940 | 0.2891 | 0.036* | |
C12 | 0.8387 (5) | 0.8793 (3) | 0.4085 (2) | 0.0375 (7) | |
H12A | 0.9841 | 0.8913 | 0.4015 | 0.045* | |
H12B | 0.7602 | 0.9679 | 0.4267 | 0.045* | |
C13 | 0.7957 (5) | 0.7645 (3) | 0.4950 (2) | 0.0403 (7) | |
H13 | 0.8211 | 0.7948 | 0.5636 | 0.048* | |
C14 | 0.5732 (5) | 0.7302 (4) | 0.4991 (3) | 0.0448 (8) | |
H14 | 0.5565 | 0.6520 | 0.5525 | 0.054* | |
C15 | 0.5425 (5) | 0.6792 (3) | 0.3908 (3) | 0.0416 (7) | |
H15A | 0.5080 | 0.5833 | 0.4000 | 0.050* | |
H15B | 0.4293 | 0.7383 | 0.3604 | 0.050* | |
C16 | 0.9390 (6) | 0.6319 (4) | 0.4702 (3) | 0.0552 (9) | |
H16A | 0.9112 | 0.5568 | 0.5235 | 0.066* | |
H16B | 1.0810 | 0.6492 | 0.4716 | 0.066* | |
C17 | 0.9077 (6) | 0.5873 (3) | 0.3616 (3) | 0.0479 (8) | |
H17A | 1.0331 | 0.5918 | 0.3147 | 0.057* | |
H17B | 0.8744 | 0.4912 | 0.3674 | 0.057* | |
C18 | 0.4096 (6) | 0.8492 (5) | 0.5265 (3) | 0.0603 (10) | |
H18 | 0.4112 | 0.9332 | 0.4846 | 0.072* | |
C19 | 0.2669 (8) | 0.8434 (7) | 0.6040 (4) | 0.0956 (17) | |
H19A | 0.2607 | 0.7611 | 0.6476 | 0.115* | |
H19B | 0.1706 | 0.9214 | 0.6163 | 0.115* | |
C20 | 0.4057 (5) | 0.3533 (3) | 0.5605 (3) | 0.0459 (8) | |
H20 | 0.5385 | 0.3793 | 0.5509 | 0.055* | |
C21 | 0.2819 (6) | 0.3798 (4) | 0.6534 (3) | 0.0533 (9) | |
H21 | 0.3335 | 0.4233 | 0.7058 | 0.064* | |
C22 | 0.0840 (6) | 0.3432 (3) | 0.6697 (3) | 0.0525 (9) | |
C23 | 0.0134 (6) | 0.2757 (4) | 0.5911 (3) | 0.0519 (9) | |
H23 | −0.1182 | 0.2479 | 0.6010 | 0.062* | |
C24 | 0.1346 (5) | 0.2489 (3) | 0.4985 (3) | 0.0417 (7) | |
H24 | 0.0837 | 0.2041 | 0.4465 | 0.050* | |
C25 | 0.3305 (5) | 0.2881 (3) | 0.4825 (2) | 0.0368 (7) | |
C26 | −0.0543 (9) | 0.3810 (5) | 0.7683 (4) | 0.0882 (16) | |
H26A | −0.0753 | 0.4814 | 0.7713 | 0.106* | |
H26B | 0.0095 | 0.3390 | 0.8297 | 0.106* | |
H26C | −0.1848 | 0.3464 | 0.7666 | 0.106* | |
C27 | 0.0573 (5) | 0.8849 (3) | 0.8753 (3) | 0.0444 (8) | |
H27 | 0.1840 | 0.9102 | 0.8882 | 0.053* | |
C28 | −0.0753 (6) | 0.9765 (4) | 0.8173 (3) | 0.0483 (8) | |
H28 | −0.0364 | 1.0638 | 0.7919 | 0.058* | |
C29 | −0.2646 (5) | 0.9418 (3) | 0.7962 (3) | 0.0414 (7) | |
C30 | −0.3163 (5) | 0.8120 (4) | 0.8344 (3) | 0.0480 (8) | |
H30 | −0.4415 | 0.7857 | 0.8199 | 0.058* | |
C31 | −0.1889 (5) | 0.7196 (3) | 0.8935 (3) | 0.0435 (8) | |
H31 | −0.2297 | 0.6332 | 0.9198 | 0.052* | |
C32 | 0.0000 (5) | 0.7552 (3) | 0.9138 (2) | 0.0361 (7) | |
C33 | −0.4060 (7) | 1.0453 (4) | 0.7338 (3) | 0.0613 (10) | |
H33A | −0.3477 | 1.0553 | 0.6618 | 0.074* | |
H33B | −0.4224 | 1.1349 | 0.7639 | 0.074* | |
H33C | −0.5381 | 1.0115 | 0.7361 | 0.074* | |
O8 | 0.5883 (4) | 0.5667 (3) | 0.15909 (18) | 0.0458 (5) | |
H1N | 0.909 (9) | 1.395 (6) | 0.085 (5) | 0.12 (2)* | |
H2N | 0.685 (6) | 0.657 (4) | 0.253 (3) | 0.064 (11)* | |
H0A | 0.527 (6) | 0.509 (4) | 0.197 (3) | 0.092 (12)* | |
H0B | 0.508 (5) | 0.608 (4) | 0.118 (3) | 0.092 (12)* |
U11 | U22 | U33 | U12 | U13 | U23 | |
S1 | 0.0337 (4) | 0.0366 (4) | 0.0455 (4) | −0.0064 (3) | −0.0059 (3) | −0.0052 (3) |
S2 | 0.0451 (5) | 0.0307 (4) | 0.0525 (5) | −0.0003 (3) | −0.0105 (4) | −0.0007 (3) |
O1 | 0.0356 (12) | 0.0437 (13) | 0.0527 (13) | 0.0104 (10) | −0.0044 (10) | −0.0088 (11) |
O2 | 0.0383 (13) | 0.0718 (18) | 0.0735 (18) | −0.0126 (12) | −0.0044 (12) | −0.0157 (14) |
O3 | 0.0505 (14) | 0.0423 (12) | 0.0575 (14) | −0.0069 (10) | −0.0040 (11) | −0.0153 (11) |
O4 | 0.0587 (15) | 0.0480 (13) | 0.0488 (13) | −0.0105 (11) | −0.0056 (12) | 0.0022 (11) |
O5 | 0.0440 (13) | 0.0492 (13) | 0.0481 (13) | −0.0026 (10) | −0.0112 (11) | 0.0016 (11) |
O6 | 0.0700 (18) | 0.0528 (16) | 0.101 (2) | −0.0305 (14) | −0.0237 (16) | 0.0334 (15) |
O7 | 0.081 (2) | 0.0642 (18) | 0.081 (2) | 0.0317 (15) | −0.0231 (17) | −0.0302 (16) |
N1 | 0.0542 (17) | 0.0307 (13) | 0.0417 (15) | −0.0108 (12) | 0.0004 (13) | −0.0022 (11) |
N2 | 0.0419 (14) | 0.0261 (12) | 0.0446 (15) | −0.0052 (10) | −0.0121 (12) | −0.0067 (11) |
C1 | 0.0419 (16) | 0.0292 (14) | 0.0316 (15) | −0.0043 (12) | 0.0027 (12) | −0.0055 (12) |
C2 | 0.060 (2) | 0.0364 (17) | 0.0402 (18) | 0.0069 (15) | −0.0039 (16) | −0.0011 (14) |
C3 | 0.054 (2) | 0.053 (2) | 0.0434 (19) | 0.0095 (16) | −0.0151 (16) | −0.0064 (16) |
C4 | 0.0474 (19) | 0.058 (2) | 0.0403 (18) | −0.0059 (16) | −0.0107 (15) | −0.0099 (16) |
C5 | 0.0407 (16) | 0.0319 (15) | 0.0410 (17) | −0.0078 (13) | −0.0070 (13) | −0.0042 (13) |
C6 | 0.0338 (14) | 0.0311 (14) | 0.0278 (14) | −0.0019 (11) | 0.0008 (11) | −0.0061 (11) |
C7 | 0.0338 (15) | 0.0300 (14) | 0.0342 (15) | −0.0041 (11) | −0.0007 (12) | −0.0069 (12) |
C8 | 0.0342 (16) | 0.0417 (17) | 0.0420 (17) | −0.0027 (13) | −0.0065 (13) | −0.0056 (14) |
C9 | 0.0468 (18) | 0.0413 (18) | 0.0473 (19) | −0.0181 (15) | −0.0033 (15) | −0.0111 (15) |
C10 | 0.0337 (15) | 0.0299 (14) | 0.0369 (16) | 0.0002 (12) | −0.0043 (12) | −0.0060 (12) |
C11 | 0.0314 (14) | 0.0217 (12) | 0.0384 (15) | −0.0013 (11) | −0.0085 (12) | −0.0050 (11) |
C12 | 0.0409 (16) | 0.0350 (16) | 0.0392 (16) | −0.0100 (13) | −0.0035 (13) | −0.0105 (13) |
C13 | 0.0491 (18) | 0.0409 (16) | 0.0339 (16) | −0.0087 (14) | −0.0140 (13) | −0.0026 (13) |
C14 | 0.058 (2) | 0.0421 (17) | 0.0372 (17) | −0.0157 (15) | −0.0076 (15) | −0.0005 (14) |
C15 | 0.0457 (17) | 0.0361 (16) | 0.0449 (18) | −0.0102 (13) | −0.0066 (14) | −0.0038 (13) |
C16 | 0.061 (2) | 0.0427 (18) | 0.064 (2) | −0.0009 (16) | −0.0270 (19) | 0.0053 (16) |
C17 | 0.058 (2) | 0.0223 (14) | 0.062 (2) | 0.0040 (14) | −0.0154 (17) | 0.0002 (14) |
C18 | 0.052 (2) | 0.070 (3) | 0.065 (2) | −0.0170 (18) | 0.0024 (19) | −0.029 (2) |
C19 | 0.073 (3) | 0.130 (5) | 0.091 (4) | −0.019 (3) | 0.009 (3) | −0.056 (3) |
C20 | 0.0477 (18) | 0.0420 (18) | 0.0500 (19) | −0.0038 (14) | −0.0187 (15) | −0.0008 (15) |
C21 | 0.077 (3) | 0.0454 (19) | 0.0392 (18) | −0.0060 (18) | −0.0161 (18) | −0.0029 (15) |
C22 | 0.071 (2) | 0.0345 (17) | 0.047 (2) | 0.0030 (16) | 0.0038 (17) | −0.0004 (15) |
C23 | 0.048 (2) | 0.0401 (18) | 0.066 (2) | −0.0050 (15) | 0.0011 (17) | −0.0056 (17) |
C24 | 0.0444 (18) | 0.0348 (16) | 0.0469 (18) | −0.0057 (13) | −0.0060 (15) | −0.0048 (14) |
C25 | 0.0405 (16) | 0.0289 (15) | 0.0415 (17) | −0.0014 (12) | −0.0108 (13) | −0.0022 (12) |
C26 | 0.117 (4) | 0.076 (3) | 0.066 (3) | −0.002 (3) | 0.019 (3) | −0.019 (2) |
C27 | 0.0487 (19) | 0.0363 (17) | 0.0503 (19) | −0.0135 (14) | −0.0081 (15) | 0.0013 (14) |
C28 | 0.057 (2) | 0.0382 (17) | 0.050 (2) | −0.0119 (15) | −0.0079 (16) | 0.0061 (15) |
C29 | 0.0445 (18) | 0.0410 (17) | 0.0383 (17) | 0.0006 (14) | −0.0065 (14) | −0.0058 (13) |
C30 | 0.0416 (18) | 0.0431 (18) | 0.062 (2) | −0.0068 (14) | −0.0110 (16) | −0.0119 (16) |
C31 | 0.0392 (17) | 0.0311 (16) | 0.061 (2) | −0.0072 (13) | −0.0040 (15) | −0.0017 (14) |
C32 | 0.0412 (16) | 0.0295 (15) | 0.0374 (17) | −0.0004 (12) | −0.0035 (13) | −0.0068 (12) |
C33 | 0.069 (2) | 0.056 (2) | 0.059 (2) | 0.0010 (19) | −0.0218 (19) | 0.0001 (18) |
O8 | 0.0472 (13) | 0.0493 (14) | 0.0449 (13) | −0.0141 (11) | −0.0135 (10) | −0.0029 (11) |
S1—O2 | 1.438 (3) | C14—C15 | 1.543 (4) |
S1—O3 | 1.439 (2) | C14—H14 | 0.9800 |
S1—O4 | 1.460 (3) | C15—H15A | 0.9700 |
S1—C25 | 1.775 (3) | C15—H15B | 0.9700 |
S2—O7 | 1.432 (3) | C16—C17 | 1.524 (5) |
S2—O6 | 1.451 (3) | C16—H16A | 0.9700 |
S2—O5 | 1.462 (2) | C16—H16B | 0.9700 |
S2—C32 | 1.762 (3) | C17—H17A | 0.9700 |
O1—C10 | 1.413 (4) | C17—H17B | 0.9700 |
O1—H1O | 0.8200 | C18—C19 | 1.293 (6) |
N1—C9 | 1.310 (5) | C18—H18 | 0.9300 |
N1—C1 | 1.373 (4) | C19—H19A | 0.9300 |
N1—H1N | 0.98 (6) | C19—H19B | 0.9300 |
N2—C15 | 1.489 (4) | C20—C25 | 1.382 (4) |
N2—C17 | 1.500 (4) | C20—C21 | 1.388 (5) |
N2—C11 | 1.509 (4) | C20—H20 | 0.9300 |
N2—H2N | 0.99 (4) | C21—C22 | 1.379 (6) |
C1—C2 | 1.395 (4) | C21—H21 | 0.9300 |
C1—C6 | 1.422 (4) | C22—C23 | 1.385 (5) |
C2—C3 | 1.353 (5) | C22—C26 | 1.514 (6) |
C2—H2 | 0.9300 | C23—C24 | 1.377 (5) |
C3—C4 | 1.409 (5) | C23—H23 | 0.9300 |
C3—H3 | 0.9300 | C24—C25 | 1.376 (4) |
C4—C5 | 1.344 (5) | C24—H24 | 0.9300 |
C4—H4 | 0.9300 | C26—H26A | 0.9600 |
C5—C6 | 1.413 (4) | C26—H26B | 0.9600 |
C5—H5 | 0.9300 | C26—H26C | 0.9600 |
C6—C7 | 1.419 (4) | C27—C28 | 1.381 (5) |
C7—C8 | 1.369 (4) | C27—C32 | 1.383 (4) |
C7—C10 | 1.514 (4) | C27—H27 | 0.9300 |
C8—C9 | 1.384 (4) | C28—C29 | 1.385 (5) |
C8—H8 | 0.9300 | C28—H28 | 0.9300 |
C9—H9 | 0.9300 | C29—C30 | 1.370 (5) |
C10—C11 | 1.540 (4) | C29—C33 | 1.506 (5) |
C10—H10 | 0.9800 | C30—C31 | 1.373 (5) |
C11—C12 | 1.540 (4) | C30—H30 | 0.9300 |
C11—H11 | 0.9800 | C31—C32 | 1.382 (4) |
C12—C13 | 1.524 (4) | C31—H31 | 0.9300 |
C12—H12A | 0.9700 | C33—H33A | 0.9600 |
C12—H12B | 0.9700 | C33—H33B | 0.9600 |
C13—C16 | 1.519 (5) | C33—H33C | 0.9600 |
C13—C14 | 1.533 (5) | O8—H0A | 0.823 (10) |
C13—H13 | 0.9800 | O8—H0B | 0.829 (10) |
C14—C18 | 1.502 (5) | ||
O2—S1—O3 | 114.45 (15) | C18—C14—H14 | 107.9 |
O2—S1—O4 | 113.09 (16) | C13—C14—H14 | 107.9 |
O3—S1—O4 | 111.37 (15) | C15—C14—H14 | 107.9 |
O2—S1—C25 | 106.39 (15) | N2—C15—C14 | 110.0 (3) |
O3—S1—C25 | 106.34 (15) | N2—C15—H15A | 109.7 |
O4—S1—C25 | 104.29 (14) | C14—C15—H15A | 109.7 |
O7—S2—O6 | 116.4 (2) | N2—C15—H15B | 109.7 |
O7—S2—O5 | 111.29 (17) | C14—C15—H15B | 109.7 |
O6—S2—O5 | 110.07 (16) | H15A—C15—H15B | 108.2 |
O7—S2—C32 | 106.87 (16) | C13—C16—C17 | 110.3 (3) |
O6—S2—C32 | 105.82 (16) | C13—C16—H16A | 109.6 |
O5—S2—C32 | 105.61 (14) | C17—C16—H16A | 109.6 |
C10—O1—H1O | 109.5 | C13—C16—H16B | 109.6 |
C9—N1—C1 | 123.2 (3) | C17—C16—H16B | 109.6 |
C9—N1—H1N | 120 (3) | H16A—C16—H16B | 108.1 |
C1—N1—H1N | 116 (3) | N2—C17—C16 | 108.4 (3) |
C15—N2—C17 | 110.0 (3) | N2—C17—H17A | 110.0 |
C15—N2—C11 | 107.6 (2) | C16—C17—H17A | 110.0 |
C17—N2—C11 | 113.4 (2) | N2—C17—H17B | 110.0 |
C15—N2—H2N | 99 (2) | C16—C17—H17B | 110.0 |
C17—N2—H2N | 116 (2) | H17A—C17—H17B | 108.4 |
C11—N2—H2N | 110 (2) | C19—C18—C14 | 124.7 (5) |
N1—C1—C2 | 120.3 (3) | C19—C18—H18 | 117.6 |
N1—C1—C6 | 118.0 (3) | C14—C18—H18 | 117.6 |
C2—C1—C6 | 121.7 (3) | C18—C19—H19A | 120.0 |
C3—C2—C1 | 119.3 (3) | C18—C19—H19B | 120.0 |
C3—C2—H2 | 120.3 | H19A—C19—H19B | 120.0 |
C1—C2—H2 | 120.3 | C25—C20—C21 | 119.6 (3) |
C2—C3—C4 | 120.5 (3) | C25—C20—H20 | 120.2 |
C2—C3—H3 | 119.7 | C21—C20—H20 | 120.2 |
C4—C3—H3 | 119.7 | C22—C21—C20 | 121.6 (3) |
C5—C4—C3 | 120.6 (3) | C22—C21—H21 | 119.2 |
C5—C4—H4 | 119.7 | C20—C21—H21 | 119.2 |
C3—C4—H4 | 119.7 | C21—C22—C23 | 117.8 (3) |
C4—C5—C6 | 121.7 (3) | C21—C22—C26 | 121.0 (4) |
C4—C5—H5 | 119.1 | C23—C22—C26 | 121.1 (4) |
C6—C5—H5 | 119.1 | C24—C23—C22 | 121.3 (3) |
C5—C6—C7 | 125.4 (3) | C24—C23—H23 | 119.4 |
C5—C6—C1 | 116.2 (3) | C22—C23—H23 | 119.4 |
C7—C6—C1 | 118.4 (3) | C25—C24—C23 | 120.4 (3) |
C8—C7—C6 | 119.5 (3) | C25—C24—H24 | 119.8 |
C8—C7—C10 | 120.0 (3) | C23—C24—H24 | 119.8 |
C6—C7—C10 | 120.4 (2) | C24—C25—C20 | 119.5 (3) |
C7—C8—C9 | 120.1 (3) | C24—C25—S1 | 119.9 (2) |
C7—C8—H8 | 119.9 | C20—C25—S1 | 120.5 (3) |
C9—C8—H8 | 119.9 | C22—C26—H26A | 109.5 |
N1—C9—C8 | 120.8 (3) | C22—C26—H26B | 109.5 |
N1—C9—H9 | 119.6 | H26A—C26—H26B | 109.5 |
C8—C9—H9 | 119.6 | C22—C26—H26C | 109.5 |
O1—C10—C7 | 111.1 (2) | H26A—C26—H26C | 109.5 |
O1—C10—C11 | 110.5 (2) | H26B—C26—H26C | 109.5 |
C7—C10—C11 | 109.0 (2) | C28—C27—C32 | 119.4 (3) |
O1—C10—H10 | 108.8 | C28—C27—H27 | 120.3 |
C7—C10—H10 | 108.8 | C32—C27—H27 | 120.3 |
C11—C10—H10 | 108.8 | C27—C28—C29 | 121.7 (3) |
N2—C11—C10 | 111.3 (2) | C27—C28—H28 | 119.1 |
N2—C11—C12 | 108.3 (2) | C29—C28—H28 | 119.1 |
C10—C11—C12 | 114.8 (2) | C30—C29—C28 | 117.5 (3) |
N2—C11—H11 | 107.4 | C30—C29—C33 | 122.3 (3) |
C10—C11—H11 | 107.4 | C28—C29—C33 | 120.2 (3) |
C12—C11—H11 | 107.4 | C29—C30—C31 | 122.0 (3) |
C13—C12—C11 | 109.0 (2) | C29—C30—H30 | 119.0 |
C13—C12—H12A | 109.9 | C31—C30—H30 | 119.0 |
C11—C12—H12A | 109.9 | C30—C31—C32 | 119.9 (3) |
C13—C12—H12B | 109.9 | C30—C31—H31 | 120.0 |
C11—C12—H12B | 109.9 | C32—C31—H31 | 120.0 |
H12A—C12—H12B | 108.3 | C31—C32—C27 | 119.3 (3) |
C16—C13—C12 | 108.4 (3) | C31—C32—S2 | 121.0 (2) |
C16—C13—C14 | 108.0 (3) | C27—C32—S2 | 119.6 (2) |
C12—C13—C14 | 111.2 (3) | C29—C33—H33A | 109.5 |
C16—C13—H13 | 109.7 | C29—C33—H33B | 109.5 |
C12—C13—H13 | 109.7 | H33A—C33—H33B | 109.5 |
C14—C13—H13 | 109.7 | C29—C33—H33C | 109.5 |
C18—C14—C13 | 115.2 (3) | H33A—C33—H33C | 109.5 |
C18—C14—C15 | 109.8 (3) | H33B—C33—H33C | 109.5 |
C13—C14—C15 | 107.9 (3) | H0A—O8—H0B | 108.0 (17) |
C9—N1—C1—C2 | 180.0 (3) | C11—N2—C15—C14 | −61.4 (3) |
C9—N1—C1—C6 | −0.3 (4) | C18—C14—C15—N2 | 124.3 (3) |
N1—C1—C2—C3 | −178.6 (3) | C13—C14—C15—N2 | −2.0 (3) |
C6—C1—C2—C3 | 1.6 (5) | C12—C13—C16—C17 | −57.7 (4) |
C1—C2—C3—C4 | −1.2 (5) | C14—C13—C16—C17 | 62.9 (4) |
C2—C3—C4—C5 | 0.2 (5) | C15—N2—C17—C16 | −59.1 (3) |
C3—C4—C5—C6 | 0.3 (5) | C11—N2—C17—C16 | 61.5 (4) |
C4—C5—C6—C7 | 179.6 (3) | C13—C16—C17—N2 | −3.7 (4) |
C4—C5—C6—C1 | 0.2 (4) | C13—C14—C18—C19 | −124.1 (4) |
N1—C1—C6—C5 | 179.2 (3) | C15—C14—C18—C19 | 113.9 (4) |
C2—C1—C6—C5 | −1.1 (4) | C25—C20—C21—C22 | −0.3 (5) |
N1—C1—C6—C7 | −0.3 (4) | C20—C21—C22—C23 | 1.4 (5) |
C2—C1—C6—C7 | 179.4 (3) | C20—C21—C22—C26 | −176.1 (4) |
C5—C6—C7—C8 | −179.2 (3) | C21—C22—C23—C24 | −1.5 (5) |
C1—C6—C7—C8 | 0.2 (4) | C26—C22—C23—C24 | 176.0 (4) |
C5—C6—C7—C10 | 1.9 (4) | C22—C23—C24—C25 | 0.5 (5) |
C1—C6—C7—C10 | −178.6 (2) | C23—C24—C25—C20 | 0.7 (4) |
C6—C7—C8—C9 | 0.4 (4) | C23—C24—C25—S1 | −175.7 (3) |
C10—C7—C8—C9 | 179.3 (3) | C21—C20—C25—C24 | −0.8 (5) |
C1—N1—C9—C8 | 1.0 (5) | C21—C20—C25—S1 | 175.6 (2) |
C7—C8—C9—N1 | −1.0 (5) | O2—S1—C25—C24 | −165.1 (2) |
C8—C7—C10—O1 | −22.6 (4) | O3—S1—C25—C24 | −42.7 (3) |
C6—C7—C10—O1 | 156.2 (2) | O4—S1—C25—C24 | 75.1 (3) |
C8—C7—C10—C11 | 99.3 (3) | O2—S1—C25—C20 | 18.5 (3) |
C6—C7—C10—C11 | −81.8 (3) | O3—S1—C25—C20 | 140.9 (2) |
C15—N2—C11—C10 | −164.0 (2) | O4—S1—C25—C20 | −101.3 (3) |
C17—N2—C11—C10 | 74.1 (3) | C32—C27—C28—C29 | −0.3 (5) |
C15—N2—C11—C12 | 68.9 (3) | C27—C28—C29—C30 | −0.4 (5) |
C17—N2—C11—C12 | −53.0 (3) | C27—C28—C29—C33 | 179.3 (3) |
O1—C10—C11—N2 | −75.9 (3) | C28—C29—C30—C31 | 1.3 (5) |
C7—C10—C11—N2 | 161.8 (2) | C33—C29—C30—C31 | −178.3 (3) |
O1—C10—C11—C12 | 47.6 (3) | C29—C30—C31—C32 | −1.6 (5) |
C7—C10—C11—C12 | −74.7 (3) | C30—C31—C32—C27 | 0.8 (5) |
N2—C11—C12—C13 | −10.7 (3) | C30—C31—C32—S2 | −175.5 (3) |
C10—C11—C12—C13 | −135.8 (3) | C28—C27—C32—C31 | 0.1 (5) |
C11—C12—C13—C16 | 65.9 (3) | C28—C27—C32—S2 | 176.5 (3) |
C11—C12—C13—C14 | −52.6 (3) | O7—S2—C32—C31 | 90.1 (3) |
C16—C13—C14—C18 | 178.1 (3) | O6—S2—C32—C31 | −34.6 (3) |
C12—C13—C14—C18 | −63.1 (4) | O5—S2—C32—C31 | −151.3 (2) |
C16—C13—C14—C15 | −58.8 (3) | O7—S2—C32—C27 | −86.3 (3) |
C12—C13—C14—C15 | 60.0 (3) | O6—S2—C32—C27 | 149.1 (3) |
C17—N2—C15—C14 | 62.6 (3) | O5—S2—C32—C27 | 32.4 (3) |
D—H···A | D—H | H···A | D···A | D—H···A |
N1—H1N···O6i | 0.98 (6) | 1.86 (6) | 2.749 (4) | 150 (5) |
N2—H2N···O8 | 0.99 (4) | 1.75 (4) | 2.718 (3) | 164 (4) |
O1—H1O···O5ii | 0.82 | 1.96 | 2.754 (3) | 163 |
O8—H0A···O4 | 0.82 (1) | 1.91 (1) | 2.731 (4) | 179 (5) |
O8—H0B···O5iii | 0.83 (1) | 1.98 (1) | 2.806 (3) | 172 (4) |
C8—H8···O3iv | 0.93 | 2.46 | 3.205 (4) | 138 |
C9—H9···O4iv | 0.93 | 2.34 | 3.247 (4) | 164 |
C11—H11···O3v | 0.98 | 2.51 | 3.320 (4) | 140 |
C17—H17A···O1 | 0.97 | 2.39 | 3.026 (4) | 123 |
C17—H17B···O2 | 0.97 | 2.50 | 3.441 (3) | 164 |
Symmetry codes: (i) x+1, y+1, z−1; (ii) x+1, y, z−1; (iii) x, y, z−1; (iv) x+1, y+1, z; (v) x, y+1, z. |
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