In the title compound, C
24H
27N
3O
2S·C
2H
6O, the dihedral angle between the least-squares planes of the 2,5-dihydroxybenzene ring and the mesityl group is 78.59 (6)°. An intramolecular O—H
N hydrogen bond is observed in the molecular structure. Centrosymmetrically related molecules are linked by N—H
O intermolecular hydrogen bonds to form a dimer. The dimers are interlinked by O—H
O and O—H
N intermolecular hydrogen bonds involving the ethanol molecule of crystallization to form chains along the
a axis.
Supporting information
CCDC reference: 270273
Key indicators
- Single-crystal X-ray study
- T = 293 K
- Mean (C-C) = 0.003 Å
- R factor = 0.035
- wR factor = 0.075
- Data-to-parameter ratio = 14.4
checkCIF/PLATON results
No syntax errors found
Alert level C
PLAT066_ALERT_1_C Predicted and Reported Transmissions Identical . ?
PLAT199_ALERT_1_C Check the Reported cell_measurement_temperature 293
PLAT200_ALERT_1_C Check the Reported cell_ambient_temperature .... 293
PLAT360_ALERT_2_C Short C(sp3)-C(sp3) Bond C25 - C26 ... 1.41 Ang.
0 ALERT level A = In general: serious problem
0 ALERT level B = Potentially serious problem
4 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
0 ALERT type 3 Indicator that the structure quality may be low
0 ALERT type 4 Improvement, methodology, query or suggestion
Data collection: X-AREA (Stoe & Cie, 2002); cell refinement: X-AREA; data reduction: X-RED32 (Stoe & Cie, 2002); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); 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).
2-({4-[3-Methyl-3-(2,4,6-trimethylphenyl)cyclobutyl]-3
H-thiazol-2-
ylidene}hydrazonomethyl)benzene-1,4-diol ethanol solvate
top
Crystal data top
C24H27N3O2S·C2H6O | Z = 2 |
Mr = 467.61 | F(000) = 500 |
Triclinic, P1 | Dx = 1.240 Mg m−3 |
Hall symbol: -P 1 | Mo Kα radiation, λ = 0.71073 Å |
a = 7.5304 (9) Å | Cell parameters from 8264 reflections |
b = 12.5739 (16) Å | θ = 1.5–26.6° |
c = 14.5935 (18) Å | µ = 0.16 mm−1 |
α = 65.678 (9)° | T = 293 K |
β = 84.257 (10)° | Prism, yellow |
γ = 89.335 (10)° | 0.30 × 0.28 × 0.27 mm |
V = 1252.2 (3) Å3 | |
Data collection top
Stoe IPDS-II diffractometer | 4402 independent reflections |
Radiation source: fine-focus sealed tube | 2329 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.050 |
Detector resolution: 6.67 pixels mm-1 | θmax = 25.0°, θmin = 1.5° |
φ scans | h = −8→8 |
Absorption correction: integration (X-RED32; Stoe & Cie, 2002) | k = −14→14 |
Tmin = 0.953, Tmax = 0.958 | l = −17→17 |
16210 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) = 0.075 | H atoms treated by a mixture of independent and constrained refinement |
S = 0.80 | w = 1/[σ2(Fo2) + (0.034P)2] where P = (Fo2 + 2Fc2)/3 |
4402 reflections | (Δ/σ)max = 0.001 |
306 parameters | Δρmax = 0.18 e Å−3 |
0 restraints | Δρmin = −0.15 e Å−3 |
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 | |
S1 | 0.18098 (7) | 0.36650 (5) | 0.04617 (4) | 0.06114 (17) | |
O1 | −0.27888 (19) | 0.36475 (11) | −0.07119 (11) | 0.0729 (4) | |
H1O | −0.1913 | 0.3381 | −0.0410 | 0.109* | |
O2 | −0.5692 (2) | 0.03839 (13) | −0.18101 (12) | 0.0755 (4) | |
H2O | −0.6693 | 0.0552 | −0.1991 | 0.113* | |
N1 | 0.3472 (2) | 0.18295 (15) | 0.13837 (13) | 0.0566 (5) | |
N2 | 0.0968 (2) | 0.14371 (14) | 0.07395 (13) | 0.0613 (5) | |
N3 | −0.0395 (2) | 0.20167 (14) | 0.01557 (12) | 0.0584 (4) | |
C1 | 0.6058 (3) | 0.24121 (16) | 0.20092 (15) | 0.0575 (5) | |
H1 | 0.6818 | 0.1926 | 0.1764 | 0.069* | |
C2 | 0.5856 (3) | 0.18810 (17) | 0.31758 (15) | 0.0625 (6) | |
H2A | 0.6034 | 0.1047 | 0.3483 | 0.075* | |
H2B | 0.4753 | 0.2075 | 0.3468 | 0.075* | |
C3 | 0.7508 (3) | 0.26306 (16) | 0.31497 (14) | 0.0552 (5) | |
C4 | 0.7171 (3) | 0.34050 (16) | 0.20335 (14) | 0.0562 (5) | |
H4A | 0.6494 | 0.4092 | 0.1957 | 0.067* | |
H4B | 0.8248 | 0.3612 | 0.1565 | 0.067* | |
C5 | 0.7430 (2) | 0.32133 (17) | 0.38812 (15) | 0.0525 (5) | |
C6 | 0.6674 (3) | 0.26230 (18) | 0.48905 (16) | 0.0613 (6) | |
C7 | 0.6559 (3) | 0.3201 (2) | 0.55256 (16) | 0.0676 (6) | |
H7 | 0.6030 | 0.2806 | 0.6185 | 0.081* | |
C8 | 0.7192 (3) | 0.4330 (2) | 0.52248 (17) | 0.0646 (6) | |
C9 | 0.8031 (3) | 0.48646 (18) | 0.42590 (17) | 0.0633 (6) | |
H9 | 0.8523 | 0.5614 | 0.4047 | 0.076* | |
C10 | 0.8180 (2) | 0.43386 (17) | 0.35822 (15) | 0.0556 (5) | |
C11 | 0.9235 (3) | 0.50199 (18) | 0.25684 (15) | 0.0678 (6) | |
H11A | 1.0079 | 0.4521 | 0.2419 | 0.102* | |
H11B | 0.9859 | 0.5669 | 0.2590 | 0.102* | |
H11C | 0.8434 | 0.5303 | 0.2053 | 0.102* | |
C12 | 0.6998 (3) | 0.4942 (2) | 0.59285 (17) | 0.0859 (8) | |
H12A | 0.7098 | 0.4385 | 0.6608 | 0.129* | |
H12B | 0.5852 | 0.5290 | 0.5894 | 0.129* | |
H12C | 0.7921 | 0.5538 | 0.5730 | 0.129* | |
C13 | 0.6043 (3) | 0.13554 (19) | 0.53473 (16) | 0.0841 (7) | |
H13A | 0.6912 | 0.0903 | 0.5151 | 0.126* | |
H13B | 0.4924 | 0.1289 | 0.5110 | 0.126* | |
H13C | 0.5892 | 0.1070 | 0.6071 | 0.126* | |
C14 | 0.9248 (3) | 0.19692 (19) | 0.31972 (17) | 0.0762 (7) | |
H14A | 0.9279 | 0.1600 | 0.2737 | 0.114* | |
H14B | 0.9303 | 0.1386 | 0.3872 | 0.114* | |
H14C | 1.0250 | 0.2508 | 0.3013 | 0.114* | |
C15 | 0.4436 (3) | 0.27092 (16) | 0.14748 (14) | 0.0521 (5) | |
C16 | 0.3696 (3) | 0.37415 (17) | 0.10300 (14) | 0.0594 (5) | |
H16 | 0.4144 | 0.4431 | 0.1024 | 0.071* | |
C17 | 0.2009 (3) | 0.21682 (16) | 0.08701 (14) | 0.0527 (5) | |
C18 | −0.1322 (3) | 0.13502 (18) | −0.01001 (15) | 0.0609 (5) | |
H18 | −0.1002 | 0.0576 | 0.0105 | 0.073* | |
C19 | −0.2826 (2) | 0.17230 (16) | −0.06833 (14) | 0.0510 (5) | |
C20 | −0.3539 (3) | 0.28236 (17) | −0.09508 (14) | 0.0551 (5) | |
C21 | −0.5031 (3) | 0.30825 (18) | −0.14629 (16) | 0.0664 (6) | |
H21 | −0.5535 | 0.3808 | −0.1623 | 0.080* | |
C22 | −0.5797 (3) | 0.22860 (19) | −0.17449 (15) | 0.0658 (6) | |
H22 | −0.6806 | 0.2479 | −0.2093 | 0.079* | |
C23 | −0.5071 (3) | 0.12049 (17) | −0.15125 (15) | 0.0566 (5) | |
C24 | −0.3621 (3) | 0.09298 (17) | −0.09730 (15) | 0.0587 (5) | |
H24 | −0.3152 | 0.0192 | −0.0794 | 0.070* | |
O3 | 0.0915 (2) | 0.05680 (14) | 0.77552 (12) | 0.1001 (6) | |
H3 | 0.0270 | 0.0355 | 0.8291 | 0.150* | |
C25 | −0.0013 (4) | 0.1344 (3) | 0.6963 (2) | 0.1154 (10) | |
H25A | −0.1090 | 0.0952 | 0.6930 | 0.138* | |
H25B | −0.0365 | 0.2008 | 0.7108 | 0.138* | |
C26 | 0.1027 (4) | 0.1746 (3) | 0.6018 (2) | 0.1344 (12) | |
H26A | 0.0349 | 0.2274 | 0.5504 | 0.202* | |
H26B | 0.1352 | 0.1094 | 0.5862 | 0.202* | |
H26C | 0.2088 | 0.2145 | 0.6044 | 0.202* | |
H1N | 0.386 (3) | 0.1169 (17) | 0.1537 (14) | 0.063 (7)* | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
S1 | 0.0607 (3) | 0.0533 (3) | 0.0674 (4) | 0.0077 (2) | −0.0108 (3) | −0.0220 (3) |
O1 | 0.0776 (10) | 0.0576 (9) | 0.0929 (11) | 0.0099 (8) | −0.0185 (9) | −0.0385 (8) |
O2 | 0.0721 (11) | 0.0773 (10) | 0.0916 (11) | 0.0118 (8) | −0.0341 (9) | −0.0439 (9) |
N1 | 0.0602 (11) | 0.0467 (11) | 0.0693 (12) | 0.0070 (9) | −0.0162 (9) | −0.0285 (9) |
N2 | 0.0569 (11) | 0.0585 (10) | 0.0747 (12) | 0.0094 (9) | −0.0243 (10) | −0.0300 (9) |
N3 | 0.0549 (10) | 0.0588 (10) | 0.0670 (11) | 0.0067 (9) | −0.0143 (9) | −0.0300 (9) |
C1 | 0.0545 (13) | 0.0603 (12) | 0.0643 (14) | 0.0043 (10) | −0.0103 (11) | −0.0316 (11) |
C2 | 0.0632 (14) | 0.0551 (12) | 0.0653 (14) | −0.0053 (10) | −0.0097 (11) | −0.0202 (10) |
C3 | 0.0508 (12) | 0.0570 (12) | 0.0583 (13) | 0.0039 (10) | −0.0079 (10) | −0.0239 (10) |
C4 | 0.0514 (13) | 0.0629 (13) | 0.0566 (13) | −0.0027 (10) | −0.0054 (10) | −0.0268 (10) |
C5 | 0.0409 (11) | 0.0618 (13) | 0.0531 (13) | 0.0034 (10) | −0.0099 (10) | −0.0208 (10) |
C6 | 0.0537 (13) | 0.0709 (14) | 0.0554 (14) | 0.0008 (11) | −0.0072 (11) | −0.0216 (12) |
C7 | 0.0557 (14) | 0.0917 (17) | 0.0506 (14) | 0.0052 (12) | −0.0057 (11) | −0.0246 (13) |
C8 | 0.0531 (13) | 0.0862 (17) | 0.0642 (16) | 0.0110 (12) | −0.0165 (12) | −0.0389 (13) |
C9 | 0.0566 (14) | 0.0681 (14) | 0.0707 (16) | 0.0008 (11) | −0.0161 (12) | −0.0321 (13) |
C10 | 0.0443 (12) | 0.0670 (13) | 0.0561 (13) | −0.0002 (10) | −0.0100 (10) | −0.0250 (11) |
C11 | 0.0600 (14) | 0.0737 (14) | 0.0668 (15) | −0.0156 (11) | −0.0073 (12) | −0.0255 (12) |
C12 | 0.0684 (16) | 0.125 (2) | 0.0858 (18) | 0.0141 (15) | −0.0179 (14) | −0.0632 (16) |
C13 | 0.0956 (19) | 0.0764 (16) | 0.0629 (15) | −0.0137 (13) | −0.0035 (14) | −0.0121 (12) |
C14 | 0.0703 (15) | 0.0811 (16) | 0.0841 (16) | 0.0192 (13) | −0.0159 (13) | −0.0398 (13) |
C15 | 0.0551 (13) | 0.0494 (12) | 0.0563 (13) | −0.0009 (10) | −0.0028 (10) | −0.0269 (10) |
C16 | 0.0602 (13) | 0.0526 (12) | 0.0689 (14) | −0.0004 (10) | −0.0082 (11) | −0.0281 (11) |
C17 | 0.0508 (12) | 0.0546 (12) | 0.0559 (13) | 0.0054 (10) | −0.0078 (11) | −0.0254 (10) |
C18 | 0.0636 (14) | 0.0562 (12) | 0.0707 (14) | 0.0126 (11) | −0.0166 (12) | −0.0322 (11) |
C19 | 0.0499 (12) | 0.0524 (11) | 0.0532 (12) | 0.0092 (10) | −0.0080 (10) | −0.0238 (10) |
C20 | 0.0564 (13) | 0.0539 (12) | 0.0549 (13) | 0.0061 (10) | −0.0026 (11) | −0.0233 (10) |
C21 | 0.0692 (15) | 0.0560 (13) | 0.0760 (15) | 0.0201 (11) | −0.0159 (13) | −0.0278 (12) |
C22 | 0.0553 (14) | 0.0732 (14) | 0.0687 (15) | 0.0188 (12) | −0.0181 (11) | −0.0270 (12) |
C23 | 0.0581 (13) | 0.0583 (13) | 0.0587 (13) | 0.0059 (11) | −0.0100 (11) | −0.0286 (11) |
C24 | 0.0575 (13) | 0.0562 (12) | 0.0677 (14) | 0.0134 (10) | −0.0152 (11) | −0.0292 (11) |
O3 | 0.0768 (11) | 0.1024 (12) | 0.0933 (13) | −0.0044 (9) | −0.0359 (10) | −0.0064 (10) |
C25 | 0.089 (2) | 0.128 (2) | 0.091 (2) | 0.0210 (18) | −0.0280 (19) | −0.0034 (18) |
C26 | 0.118 (3) | 0.156 (3) | 0.099 (2) | 0.019 (2) | −0.013 (2) | −0.023 (2) |
Geometric parameters (Å, º) top
S1—C17 | 1.734 (2) | C10—C11 | 1.513 (3) |
S1—C16 | 1.738 (2) | C11—H11A | 0.96 |
O1—C20 | 1.365 (2) | C11—H11B | 0.96 |
O1—H1O | 0.82 | C11—H11C | 0.96 |
O2—C23 | 1.376 (2) | C12—H12A | 0.96 |
O2—H2O | 0.82 | C12—H12B | 0.96 |
N1—C17 | 1.359 (2) | C12—H12C | 0.96 |
N1—C15 | 1.388 (2) | C13—H13A | 0.96 |
N1—H1N | 0.825 (19) | C13—H13B | 0.96 |
N2—C17 | 1.299 (2) | C13—H13C | 0.96 |
N2—N3 | 1.399 (2) | C14—H14A | 0.96 |
N3—C18 | 1.286 (2) | C14—H14B | 0.96 |
C1—C15 | 1.477 (3) | C14—H14C | 0.96 |
C1—C4 | 1.526 (3) | C15—C16 | 1.333 (2) |
C1—C2 | 1.543 (3) | C16—H16 | 0.93 |
C1—H1 | 0.98 | C18—C19 | 1.442 (3) |
C2—C3 | 1.558 (3) | C18—H18 | 0.93 |
C2—H2A | 0.97 | C19—C20 | 1.391 (2) |
C2—H2B | 0.97 | C19—C24 | 1.394 (2) |
C3—C5 | 1.520 (3) | C20—C21 | 1.374 (3) |
C3—C14 | 1.536 (3) | C21—C22 | 1.380 (3) |
C3—C4 | 1.561 (2) | C21—H21 | 0.93 |
C4—H4A | 0.97 | C22—C23 | 1.379 (3) |
C4—H4B | 0.97 | C22—H22 | 0.93 |
C5—C10 | 1.404 (3) | C23—C24 | 1.368 (3) |
C5—C6 | 1.409 (3) | C24—H24 | 0.93 |
C6—C7 | 1.390 (3) | O3—C25 | 1.412 (3) |
C6—C13 | 1.513 (3) | O3—H3 | 0.82 |
C7—C8 | 1.378 (3) | C25—C26 | 1.411 (3) |
C7—H7 | 0.93 | C25—H25A | 0.97 |
C8—C9 | 1.374 (3) | C25—H25B | 0.97 |
C8—C12 | 1.511 (3) | C26—H26A | 0.96 |
C9—C10 | 1.393 (3) | C26—H26B | 0.96 |
C9—H9 | 0.93 | C26—H26C | 0.96 |
| | | |
C17—S1—C16 | 90.50 (10) | C8—C12—H12C | 109.5 |
C20—O1—H1O | 109.5 | H12A—C12—H12C | 109.5 |
C23—O2—H2O | 109.5 | H12B—C12—H12C | 109.5 |
C17—N1—C15 | 115.95 (17) | C6—C13—H13A | 109.5 |
C17—N1—H1N | 121.4 (14) | C6—C13—H13B | 109.5 |
C15—N1—H1N | 121.7 (14) | H13A—C13—H13B | 109.5 |
C17—N2—N3 | 111.07 (16) | C6—C13—H13C | 109.5 |
C18—N3—N2 | 113.19 (16) | H13A—C13—H13C | 109.5 |
C15—C1—C4 | 118.19 (16) | H13B—C13—H13C | 109.5 |
C15—C1—C2 | 118.93 (17) | C3—C14—H14A | 109.5 |
C4—C1—C2 | 87.61 (14) | C3—C14—H14B | 109.5 |
C15—C1—H1 | 110.1 | H14A—C14—H14B | 109.5 |
C4—C1—H1 | 110.1 | C3—C14—H14C | 109.5 |
C2—C1—H1 | 110.1 | H14A—C14—H14C | 109.5 |
C1—C2—C3 | 89.74 (15) | H14B—C14—H14C | 109.5 |
C1—C2—H2A | 113.7 | C16—C15—N1 | 111.23 (18) |
C3—C2—H2A | 113.7 | C16—C15—C1 | 129.65 (18) |
C1—C2—H2B | 113.7 | N1—C15—C1 | 119.12 (16) |
C3—C2—H2B | 113.7 | C15—C16—S1 | 112.97 (15) |
H2A—C2—H2B | 110.9 | C15—C16—H16 | 123.5 |
C5—C3—C14 | 110.19 (16) | S1—C16—H16 | 123.5 |
C5—C3—C2 | 118.30 (17) | N2—C17—N1 | 122.66 (17) |
C14—C3—C2 | 111.84 (16) | N2—C17—S1 | 128.00 (15) |
C5—C3—C4 | 117.47 (15) | N1—C17—S1 | 109.33 (15) |
C14—C3—C4 | 111.22 (17) | N3—C18—C19 | 124.38 (18) |
C2—C3—C4 | 85.89 (14) | N3—C18—H18 | 117.8 |
C1—C4—C3 | 90.24 (14) | C19—C18—H18 | 117.8 |
C1—C4—H4A | 113.6 | C20—C19—C24 | 118.73 (18) |
C3—C4—H4A | 113.6 | C20—C19—C18 | 123.15 (18) |
C1—C4—H4B | 113.6 | C24—C19—C18 | 118.11 (17) |
C3—C4—H4B | 113.6 | O1—C20—C21 | 119.49 (18) |
H4A—C4—H4B | 110.9 | O1—C20—C19 | 121.37 (18) |
C10—C5—C6 | 117.99 (18) | C21—C20—C19 | 119.14 (19) |
C10—C5—C3 | 120.86 (18) | C20—C21—C22 | 121.24 (19) |
C6—C5—C3 | 121.10 (18) | C20—C21—H21 | 119.4 |
C7—C6—C5 | 119.5 (2) | C22—C21—H21 | 119.4 |
C7—C6—C13 | 117.2 (2) | C23—C22—C21 | 120.20 (19) |
C5—C6—C13 | 123.3 (2) | C23—C22—H22 | 119.9 |
C8—C7—C6 | 123.1 (2) | C21—C22—H22 | 119.9 |
C8—C7—H7 | 118.5 | C24—C23—O2 | 117.32 (17) |
C6—C7—H7 | 118.5 | C24—C23—C22 | 118.70 (19) |
C9—C8—C7 | 116.6 (2) | O2—C23—C22 | 123.97 (19) |
C9—C8—C12 | 121.8 (2) | C23—C24—C19 | 121.93 (18) |
C7—C8—C12 | 121.6 (2) | C23—C24—H24 | 119.0 |
C8—C9—C10 | 123.2 (2) | C19—C24—H24 | 119.0 |
C8—C9—H9 | 118.4 | C25—O3—H3 | 109.5 |
C10—C9—H9 | 118.4 | C26—C25—O3 | 112.4 (2) |
C9—C10—C5 | 119.44 (19) | C26—C25—H25A | 109.1 |
C9—C10—C11 | 116.44 (19) | O3—C25—H25A | 109.1 |
C5—C10—C11 | 124.07 (18) | C26—C25—H25B | 109.1 |
C10—C11—H11A | 109.5 | O3—C25—H25B | 109.1 |
C10—C11—H11B | 109.5 | H25A—C25—H25B | 107.9 |
H11A—C11—H11B | 109.5 | C25—C26—H26A | 109.5 |
C10—C11—H11C | 109.5 | C25—C26—H26B | 109.5 |
H11A—C11—H11C | 109.5 | H26A—C26—H26B | 109.5 |
H11B—C11—H11C | 109.5 | C25—C26—H26C | 109.5 |
C8—C12—H12A | 109.5 | H26A—C26—H26C | 109.5 |
C8—C12—H12B | 109.5 | H26B—C26—H26C | 109.5 |
H12A—C12—H12B | 109.5 | | |
| | | |
C17—N2—N3—C18 | 171.75 (17) | C3—C5—C10—C11 | −5.1 (3) |
C15—C1—C2—C3 | −140.46 (17) | C17—N1—C15—C16 | 0.4 (2) |
C4—C1—C2—C3 | −19.32 (14) | C17—N1—C15—C1 | −179.06 (18) |
C1—C2—C3—C5 | 138.02 (17) | C4—C1—C15—C16 | −3.8 (3) |
C1—C2—C3—C14 | −92.33 (18) | C2—C1—C15—C16 | 100.2 (2) |
C1—C2—C3—C4 | 18.91 (14) | C4—C1—C15—N1 | 175.61 (17) |
C15—C1—C4—C3 | 141.08 (17) | C2—C1—C15—N1 | −80.4 (2) |
C2—C1—C4—C3 | 19.28 (15) | N1—C15—C16—S1 | −1.2 (2) |
C5—C3—C4—C1 | −139.02 (17) | C1—C15—C16—S1 | 178.21 (17) |
C14—C3—C4—C1 | 92.73 (18) | C17—S1—C16—C15 | 1.30 (16) |
C2—C3—C4—C1 | −19.12 (15) | N3—N2—C17—N1 | −177.84 (17) |
C14—C3—C5—C10 | 87.8 (2) | N3—N2—C17—S1 | 2.8 (3) |
C2—C3—C5—C10 | −141.82 (18) | C15—N1—C17—N2 | −178.94 (18) |
C4—C3—C5—C10 | −41.0 (2) | C15—N1—C17—S1 | 0.5 (2) |
C14—C3—C5—C6 | −89.4 (2) | C16—S1—C17—N2 | 178.44 (19) |
C2—C3—C5—C6 | 41.0 (2) | C16—S1—C17—N1 | −1.00 (15) |
C4—C3—C5—C6 | 141.83 (18) | N2—N3—C18—C19 | 178.66 (18) |
C10—C5—C6—C7 | 5.4 (3) | N3—C18—C19—C20 | −6.3 (3) |
C3—C5—C6—C7 | −177.33 (17) | N3—C18—C19—C24 | 175.05 (19) |
C10—C5—C6—C13 | −171.74 (19) | C24—C19—C20—O1 | −178.22 (17) |
C3—C5—C6—C13 | 5.5 (3) | C18—C19—C20—O1 | 3.1 (3) |
C5—C6—C7—C8 | −1.6 (3) | C24—C19—C20—C21 | 2.0 (3) |
C13—C6—C7—C8 | 175.72 (19) | C18—C19—C20—C21 | −176.65 (19) |
C6—C7—C8—C9 | −2.7 (3) | O1—C20—C21—C22 | 178.04 (18) |
C6—C7—C8—C12 | 178.33 (19) | C19—C20—C21—C22 | −2.2 (3) |
C7—C8—C9—C10 | 3.1 (3) | C20—C21—C22—C23 | 0.1 (3) |
C12—C8—C9—C10 | −177.89 (18) | C21—C22—C23—C24 | 2.0 (3) |
C8—C9—C10—C5 | 0.7 (3) | C21—C22—C23—O2 | −176.47 (19) |
C8—C9—C10—C11 | −176.70 (18) | O2—C23—C24—C19 | 176.39 (18) |
C6—C5—C10—C9 | −5.0 (3) | C22—C23—C24—C19 | −2.2 (3) |
C3—C5—C10—C9 | 177.74 (17) | C20—C19—C24—C23 | 0.2 (3) |
C6—C5—C10—C11 | 172.23 (18) | C18—C19—C24—C23 | 178.9 (2) |
Hydrogen-bond geometry (Å, º) top
D—H···A | D—H | H···A | D···A | D—H···A |
N1—H1N···O2i | 0.825 (19) | 2.30 (2) | 3.099 (2) | 164 (2) |
O2—H2O···O3ii | 0.82 | 1.87 | 2.678 (2) | 167 |
O3—H3···N2iii | 0.82 | 2.26 | 2.844 (2) | 128 |
O1—H1O···N3 | 0.82 | 1.98 | 2.700 (2) | 147 |
Symmetry codes: (i) −x, −y, −z; (ii) x−1, y, z−1; (iii) −x, −y, −z+1. |