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In the title compound, C
23H
22N
2O
6S·C
2H
6O·0.5H
2O, the isovanillin group makes dihedral angles of 50.57 (8) and 8.89 (11)°, respectively, with the methyl- and methoxy-substituted benzene rings. Intramolecular N—H
O hydrogen bonds help to stabilize the molecular conformation, while intermolecular O—H
O and C—H
O hydrogen bonds link adjacent molecules, forming an infinite network.
Supporting information
CCDC reference: 629411
Key indicators
- Single-crystal X-ray study
- T = 294 K
- Mean (C-C) = 0.004 Å
- Disorder in solvent or counterion
- R factor = 0.060
- wR factor = 0.189
- Data-to-parameter ratio = 13.7
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
PLAT220_ALERT_2_C Large Non-Solvent O Ueq(max)/Ueq(min) ... 2.57 Ratio
PLAT302_ALERT_4_C Anion/Solvent Disorder ......................... 12.00 Perc.
PLAT779_ALERT_2_C Suspect or Irrelevant (Bond) Angle in CIF ...... 35.80 Deg.
O8 -O8 -H8A 2.766 1.555 1.555
0 ALERT level A = In general: serious problem
0 ALERT level B = Potentially serious problem
6 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
2 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
1 ALERT type 4 Improvement, methodology, query or suggestion
0 ALERT type 5 Informative message, check
Data collection: SMART (Bruker, 1999); cell refinement: SAINT (Bruker, 1999); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997a); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997a); molecular graphics: SHELXTL (Sheldrick, 1997b); software used to prepare material for publication: SHELXTL.
(
E)-2-Methoxy-
N'-[4-methoxy-3-(4-
methylbenzenesulfonyloxy)benzylidene]benzohydrazide ethanol solvate
hemihydrate
top
Crystal data top
C23H22N2O6S·C2H6O·0.5H2O | Z = 2 |
Mr = 509.57 | F(000) = 538 |
Triclinic, P1 | Dx = 1.313 Mg m−3 |
Hall symbol: -P 1 | Mo Kα radiation, λ = 0.71073 Å |
a = 7.9106 (16) Å | Cell parameters from 3685 reflections |
b = 8.6824 (17) Å | θ = 2.5–24.5° |
c = 19.266 (4) Å | µ = 0.17 mm−1 |
α = 87.61 (3)° | T = 294 K |
β = 80.12 (3)° | Block, colourless |
γ = 81.39 (3)° | 0.14 × 0.12 × 0.10 mm |
V = 1288.8 (5) Å3 | |
Data collection top
Bruker SMART APEX CCD area-detector diffractometer | 4492 independent reflections |
Radiation source: fine-focus sealed tube | 3294 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.027 |
φ and ω scans | θmax = 25.0°, θmin = 1.1° |
Absorption correction: multi-scan (SADABS; Sheldrick, 1996) | h = −9→6 |
Tmin = 0.954, Tmax = 0.983 | k = −10→10 |
7839 measured reflections | l = −22→18 |
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)] = 0.060 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.189 | H-atom parameters constrained |
S = 1.07 | w = 1/[σ2(Fo2) + (0.1233P)2 + 0.0157P] where P = (Fo2 + 2Fc2)/3 |
4492 reflections | (Δ/σ)max = 0.020 |
329 parameters | Δρmax = 0.40 e Å−3 |
33 restraints | Δρmin = −0.30 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 >
2σ(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 | Occ. (<1) |
S1 | 0.48054 (9) | 1.13752 (7) | 0.14008 (3) | 0.0590 (3) | |
O1 | 0.4491 (3) | 1.2554 (2) | 0.08864 (11) | 0.0836 (7) | |
O2 | 0.4807 (3) | 1.1777 (2) | 0.21085 (10) | 0.0786 (6) | |
O3 | 0.3281 (2) | 1.03709 (17) | 0.13871 (7) | 0.0493 (4) | |
O4 | −0.1753 (5) | 1.2724 (3) | 0.43823 (13) | 0.1266 (11) | |
O5 | 0.4644 (2) | 0.74858 (18) | 0.10306 (8) | 0.0566 (5) | |
O6 | −0.3167 (3) | 0.8955 (2) | 0.56106 (9) | 0.0721 (6) | |
N1 | −0.0337 (3) | 0.9965 (3) | 0.38248 (10) | 0.0628 (6) | |
N2 | −0.1469 (3) | 1.0107 (3) | 0.44520 (10) | 0.0634 (6) | |
H2 | −0.1732 | 0.9290 | 0.4689 | 0.076* | |
C1 | 0.6691 (3) | 1.0113 (3) | 0.10939 (12) | 0.0532 (6) | |
C2 | 0.7130 (3) | 0.9818 (3) | 0.03746 (13) | 0.0584 (6) | |
H2A | 0.6475 | 1.0347 | 0.0058 | 0.070* | |
C3 | 0.8537 (3) | 0.8741 (3) | 0.01414 (13) | 0.0632 (7) | |
H3 | 0.8832 | 0.8550 | −0.0339 | 0.076* | |
C4 | 0.9533 (3) | 0.7929 (3) | 0.05958 (15) | 0.0649 (7) | |
C5 | 0.9091 (4) | 0.8265 (4) | 0.13135 (14) | 0.0681 (7) | |
H5 | 0.9757 | 0.7746 | 0.1628 | 0.082* | |
C6 | 0.7691 (4) | 0.9347 (3) | 0.15607 (13) | 0.0652 (7) | |
H6 | 0.7415 | 0.9564 | 0.2039 | 0.078* | |
C7 | 1.1060 (4) | 0.6719 (4) | 0.03322 (18) | 0.0847 (9) | |
H7A | 1.0945 | 0.6370 | −0.0121 | 0.127* | |
H7B | 1.1095 | 0.5851 | 0.0657 | 0.127* | |
H7C | 1.2112 | 0.7166 | 0.0293 | 0.127* | |
C8 | 0.2991 (3) | 0.9162 (3) | 0.18869 (11) | 0.0449 (5) | |
C9 | 0.1931 (3) | 0.9494 (3) | 0.25173 (11) | 0.0482 (6) | |
H9 | 0.1505 | 1.0522 | 0.2638 | 0.058* | |
C10 | 0.1491 (3) | 0.8277 (3) | 0.29790 (12) | 0.0531 (6) | |
C11 | 0.2171 (4) | 0.6762 (3) | 0.27816 (14) | 0.0642 (7) | |
H11 | 0.1891 | 0.5941 | 0.3084 | 0.077* | |
C12 | 0.3262 (4) | 0.6441 (3) | 0.21420 (14) | 0.0605 (7) | |
H12 | 0.3712 | 0.5416 | 0.2024 | 0.073* | |
C13 | 0.3678 (3) | 0.7638 (3) | 0.16810 (12) | 0.0480 (5) | |
C14 | 0.5567 (4) | 0.6000 (3) | 0.08289 (16) | 0.0711 (8) | |
H14A | 0.6263 | 0.5608 | 0.1177 | 0.107* | |
H14B | 0.6303 | 0.6090 | 0.0382 | 0.107* | |
H14C | 0.4761 | 0.5297 | 0.0791 | 0.107* | |
C15 | 0.0301 (3) | 0.8591 (3) | 0.36423 (13) | 0.0620 (7) | |
H15 | 0.0007 | 0.7762 | 0.3937 | 0.074* | |
C16 | −0.2168 (4) | 1.1538 (4) | 0.46940 (14) | 0.0749 (9) | |
C17 | −0.3503 (4) | 1.1654 (3) | 0.53449 (13) | 0.0654 (7) | |
C18 | −0.4343 (5) | 1.3143 (4) | 0.55171 (15) | 0.0842 (10) | |
H18 | −0.4032 | 1.3978 | 0.5230 | 0.101* | |
C19 | −0.5612 (5) | 1.3424 (4) | 0.60940 (17) | 0.0915 (11) | |
H19 | −0.6161 | 1.4433 | 0.6196 | 0.110* | |
C20 | −0.6063 (4) | 1.2193 (5) | 0.65208 (16) | 0.0866 (10) | |
H20 | −0.6927 | 1.2374 | 0.6914 | 0.104* | |
C21 | −0.5263 (4) | 1.0705 (4) | 0.63777 (14) | 0.0737 (8) | |
H21 | −0.5571 | 0.9891 | 0.6679 | 0.088* | |
C22 | −0.3995 (4) | 1.0402 (3) | 0.57867 (12) | 0.0610 (7) | |
C23 | −0.3513 (5) | 0.7675 (4) | 0.60810 (16) | 0.0907 (10) | |
H23A | −0.3172 | 0.7838 | 0.6524 | 0.136* | |
H23B | −0.2869 | 0.6726 | 0.5880 | 0.136* | |
H23C | −0.4730 | 0.7603 | 0.6154 | 0.136* | |
O7 | 0.9880 (5) | 0.3410 (5) | 0.30123 (16) | 0.1384 (12) | |
H7 | 0.9461 | 0.4009 | 0.3336 | 0.208* | |
C24 | 0.8643 (7) | 0.3297 (7) | 0.2594 (2) | 0.146 (2) | |
H24A | 0.7638 | 0.4071 | 0.2738 | 0.175* | |
H24B | 0.8277 | 0.2276 | 0.2665 | 0.175* | |
C25 | 0.9298 (8) | 0.3527 (7) | 0.1857 (3) | 0.152 (2) | |
H25A | 0.9337 | 0.4617 | 0.1764 | 0.228* | |
H25B | 0.8547 | 0.3166 | 0.1577 | 0.228* | |
H25C | 1.0444 | 0.2959 | 0.1739 | 0.228* | |
O8 | 0.9629 (14) | 0.5486 (10) | 0.4749 (5) | 0.189 (3) | 0.50 |
H8A | 1.0564 | 0.5236 | 0.4939 | 0.226* | 0.50 |
H8B | 0.9536 | 0.5017 | 0.4370 | 0.226* | 0.50 |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
S1 | 0.0778 (5) | 0.0413 (4) | 0.0585 (4) | −0.0223 (3) | 0.0003 (3) | −0.0049 (3) |
O1 | 0.1141 (18) | 0.0416 (10) | 0.0880 (13) | −0.0181 (11) | 0.0054 (12) | 0.0124 (9) |
O2 | 0.0969 (15) | 0.0751 (13) | 0.0685 (11) | −0.0345 (11) | −0.0022 (10) | −0.0261 (10) |
O3 | 0.0591 (10) | 0.0383 (8) | 0.0503 (9) | −0.0105 (7) | −0.0065 (7) | 0.0018 (6) |
O4 | 0.172 (3) | 0.0830 (17) | 0.0943 (17) | −0.0052 (18) | 0.0475 (17) | 0.0110 (13) |
O5 | 0.0641 (11) | 0.0398 (9) | 0.0622 (10) | −0.0104 (8) | 0.0044 (8) | −0.0090 (7) |
O6 | 0.0844 (14) | 0.0739 (13) | 0.0546 (10) | −0.0168 (11) | 0.0018 (9) | 0.0016 (9) |
N1 | 0.0575 (13) | 0.0796 (16) | 0.0482 (11) | −0.0101 (12) | −0.0012 (10) | 0.0033 (10) |
N2 | 0.0613 (13) | 0.0786 (16) | 0.0472 (11) | −0.0109 (12) | −0.0006 (10) | 0.0036 (10) |
C1 | 0.0603 (15) | 0.0517 (14) | 0.0508 (13) | −0.0260 (12) | −0.0031 (11) | −0.0008 (10) |
C2 | 0.0564 (15) | 0.0716 (17) | 0.0504 (13) | −0.0245 (13) | −0.0061 (11) | 0.0042 (11) |
C3 | 0.0529 (15) | 0.085 (2) | 0.0538 (14) | −0.0245 (14) | −0.0008 (12) | −0.0057 (13) |
C4 | 0.0521 (15) | 0.0736 (18) | 0.0738 (17) | −0.0297 (13) | −0.0053 (13) | −0.0043 (14) |
C5 | 0.0644 (17) | 0.0767 (19) | 0.0696 (17) | −0.0212 (15) | −0.0203 (14) | 0.0019 (14) |
C6 | 0.0769 (19) | 0.0732 (18) | 0.0523 (14) | −0.0291 (15) | −0.0133 (13) | −0.0020 (12) |
C7 | 0.0615 (18) | 0.088 (2) | 0.104 (2) | −0.0131 (17) | −0.0067 (17) | −0.0099 (18) |
C8 | 0.0462 (12) | 0.0410 (12) | 0.0498 (12) | −0.0120 (10) | −0.0102 (10) | 0.0021 (9) |
C9 | 0.0474 (13) | 0.0457 (13) | 0.0519 (13) | −0.0079 (10) | −0.0080 (10) | −0.0022 (10) |
C10 | 0.0509 (14) | 0.0580 (15) | 0.0519 (13) | −0.0132 (11) | −0.0095 (11) | 0.0044 (10) |
C11 | 0.0704 (17) | 0.0516 (15) | 0.0698 (16) | −0.0159 (13) | −0.0075 (13) | 0.0152 (12) |
C12 | 0.0675 (17) | 0.0382 (13) | 0.0737 (16) | −0.0086 (12) | −0.0060 (13) | 0.0034 (11) |
C13 | 0.0469 (13) | 0.0398 (12) | 0.0582 (13) | −0.0093 (10) | −0.0082 (10) | −0.0034 (9) |
C14 | 0.0734 (19) | 0.0475 (15) | 0.0857 (18) | −0.0005 (13) | 0.0024 (15) | −0.0168 (13) |
C15 | 0.0590 (16) | 0.0712 (18) | 0.0561 (15) | −0.0173 (14) | −0.0072 (12) | 0.0120 (13) |
C16 | 0.083 (2) | 0.082 (2) | 0.0522 (15) | −0.0037 (17) | −0.0016 (14) | 0.0099 (14) |
C17 | 0.0667 (17) | 0.0803 (19) | 0.0470 (13) | 0.0001 (15) | −0.0138 (12) | 0.0035 (12) |
C18 | 0.089 (2) | 0.084 (2) | 0.0702 (18) | 0.0056 (18) | −0.0041 (17) | 0.0098 (15) |
C19 | 0.093 (2) | 0.094 (2) | 0.074 (2) | 0.018 (2) | −0.0039 (17) | −0.0063 (17) |
C20 | 0.071 (2) | 0.114 (3) | 0.0645 (18) | −0.002 (2) | 0.0066 (15) | −0.0094 (18) |
C21 | 0.0684 (18) | 0.094 (2) | 0.0575 (15) | −0.0160 (17) | −0.0043 (13) | −0.0002 (14) |
C22 | 0.0567 (15) | 0.0808 (19) | 0.0464 (13) | −0.0088 (14) | −0.0122 (11) | −0.0018 (12) |
C23 | 0.117 (3) | 0.080 (2) | 0.0685 (18) | −0.016 (2) | 0.0018 (18) | 0.0080 (15) |
O7 | 0.161 (3) | 0.168 (3) | 0.099 (2) | −0.069 (3) | −0.023 (2) | 0.0096 (19) |
C24 | 0.139 (4) | 0.187 (5) | 0.099 (3) | 0.023 (4) | −0.025 (3) | −0.027 (3) |
C25 | 0.168 (5) | 0.159 (4) | 0.122 (3) | 0.010 (4) | −0.039 (3) | 0.012 (3) |
O8 | 0.213 (7) | 0.156 (6) | 0.200 (7) | −0.044 (6) | −0.039 (6) | 0.032 (5) |
Geometric parameters (Å, º) top
S1—O1 | 1.420 (2) | C11—C12 | 1.390 (4) |
S1—O2 | 1.4217 (19) | C11—H11 | 0.9300 |
S1—O3 | 1.5944 (18) | C12—C13 | 1.380 (3) |
S1—C1 | 1.743 (3) | C12—H12 | 0.9300 |
O3—C8 | 1.412 (3) | C14—H14A | 0.9600 |
O4—C16 | 1.229 (4) | C14—H14B | 0.9600 |
O5—C13 | 1.351 (3) | C14—H14C | 0.9600 |
O5—C14 | 1.418 (3) | C15—H15 | 0.9300 |
O6—C22 | 1.355 (3) | C16—C17 | 1.491 (4) |
O6—C23 | 1.433 (3) | C17—C18 | 1.387 (4) |
N1—C15 | 1.263 (4) | C17—C22 | 1.412 (4) |
N1—N2 | 1.373 (3) | C18—C19 | 1.367 (4) |
N2—C16 | 1.349 (4) | C18—H18 | 0.9300 |
N2—H2 | 0.8600 | C19—C20 | 1.374 (5) |
C1—C6 | 1.383 (4) | C19—H19 | 0.9300 |
C1—C2 | 1.394 (3) | C20—C21 | 1.368 (5) |
C2—C3 | 1.366 (4) | C20—H20 | 0.9300 |
C2—H2A | 0.9300 | C21—C22 | 1.388 (4) |
C3—C4 | 1.380 (4) | C21—H21 | 0.9300 |
C3—H3 | 0.9300 | C23—H23A | 0.9600 |
C4—C5 | 1.399 (4) | C23—H23B | 0.9600 |
C4—C7 | 1.508 (4) | C23—H23C | 0.9600 |
C5—C6 | 1.371 (4) | O7—C24 | 1.386 (6) |
C5—H5 | 0.9300 | O7—H7 | 0.8200 |
C6—H6 | 0.9300 | C24—C25 | 1.443 (6) |
C7—H7A | 0.9600 | C24—H24A | 0.9700 |
C7—H7B | 0.9600 | C24—H24B | 0.9700 |
C7—H7C | 0.9600 | C25—H25A | 0.9600 |
C8—C9 | 1.367 (3) | C25—H25B | 0.9600 |
C8—C13 | 1.399 (3) | C25—H25C | 0.9600 |
C9—C10 | 1.398 (3) | O8—O8i | 1.406 (16) |
C9—H9 | 0.9300 | O8—H8A | 0.8761 |
C10—C11 | 1.387 (4) | O8—H8B | 0.8688 |
C10—C15 | 1.460 (4) | | |
| | | |
O1—S1—O2 | 120.43 (13) | C12—C13—C8 | 117.7 (2) |
O1—S1—O3 | 102.19 (12) | O5—C14—H14A | 109.5 |
O2—S1—O3 | 108.97 (11) | O5—C14—H14B | 109.5 |
O1—S1—C1 | 109.99 (12) | H14A—C14—H14B | 109.5 |
O2—S1—C1 | 109.58 (13) | O5—C14—H14C | 109.5 |
O3—S1—C1 | 104.28 (10) | H14A—C14—H14C | 109.5 |
C8—O3—S1 | 120.85 (14) | H14B—C14—H14C | 109.5 |
C13—O5—C14 | 118.53 (19) | N1—C15—C10 | 121.4 (2) |
C22—O6—C23 | 118.9 (2) | N1—C15—H15 | 119.3 |
C15—N1—N2 | 115.9 (2) | C10—C15—H15 | 119.3 |
C16—N2—N1 | 119.5 (2) | O4—C16—N2 | 121.5 (3) |
C16—N2—H2 | 120.2 | O4—C16—C17 | 120.2 (3) |
N1—N2—H2 | 120.2 | N2—C16—C17 | 118.3 (3) |
C6—C1—C2 | 120.3 (3) | C18—C17—C22 | 118.0 (3) |
C6—C1—S1 | 120.51 (19) | C18—C17—C16 | 115.8 (3) |
C2—C1—S1 | 119.1 (2) | C22—C17—C16 | 126.2 (3) |
C3—C2—C1 | 119.0 (2) | C19—C18—C17 | 122.3 (3) |
C3—C2—H2A | 120.5 | C19—C18—H18 | 118.9 |
C1—C2—H2A | 120.5 | C17—C18—H18 | 118.9 |
C2—C3—C4 | 122.1 (2) | C18—C19—C20 | 118.9 (3) |
C2—C3—H3 | 119.0 | C18—C19—H19 | 120.6 |
C4—C3—H3 | 119.0 | C20—C19—H19 | 120.6 |
C3—C4—C5 | 117.9 (3) | C21—C20—C19 | 121.1 (3) |
C3—C4—C7 | 121.5 (3) | C21—C20—H20 | 119.4 |
C5—C4—C7 | 120.6 (3) | C19—C20—H20 | 119.4 |
C6—C5—C4 | 121.1 (3) | C20—C21—C22 | 120.5 (3) |
C6—C5—H5 | 119.4 | C20—C21—H21 | 119.8 |
C4—C5—H5 | 119.4 | C22—C21—H21 | 119.8 |
C5—C6—C1 | 119.5 (2) | O6—C22—C21 | 123.4 (3) |
C5—C6—H6 | 120.2 | O6—C22—C17 | 117.3 (2) |
C1—C6—H6 | 120.2 | C21—C22—C17 | 119.2 (3) |
C4—C7—H7A | 109.5 | O6—C23—H23A | 109.5 |
C4—C7—H7B | 109.5 | O6—C23—H23B | 109.5 |
H7A—C7—H7B | 109.5 | H23A—C23—H23B | 109.5 |
C4—C7—H7C | 109.5 | O6—C23—H23C | 109.5 |
H7A—C7—H7C | 109.5 | H23A—C23—H23C | 109.5 |
H7B—C7—H7C | 109.5 | H23B—C23—H23C | 109.5 |
C9—C8—C13 | 122.6 (2) | C24—O7—H7 | 109.5 |
C9—C8—O3 | 119.6 (2) | O7—C24—C25 | 111.9 (5) |
C13—C8—O3 | 117.48 (19) | O7—C24—H24A | 109.2 |
C8—C9—C10 | 119.5 (2) | C25—C24—H24A | 109.2 |
C8—C9—H9 | 120.2 | O7—C24—H24B | 109.2 |
C10—C9—H9 | 120.2 | C25—C24—H24B | 109.2 |
C11—C10—C9 | 118.4 (2) | H24A—C24—H24B | 107.9 |
C11—C10—C15 | 120.9 (2) | C24—C25—H25A | 109.1 |
C9—C10—C15 | 120.8 (2) | C24—C25—H25B | 109.6 |
C10—C11—C12 | 121.5 (2) | H25A—C25—H25B | 109.5 |
C10—C11—H11 | 119.2 | C24—C25—H25C | 109.7 |
C12—C11—H11 | 119.2 | H25A—C25—H25C | 109.5 |
C13—C12—C11 | 120.2 (2) | H25B—C25—H25C | 109.5 |
C13—C12—H12 | 119.9 | O8i—O8—H8A | 35.8 |
C11—C12—H12 | 119.9 | O8i—O8—H8B | 114.6 |
O5—C13—C12 | 126.3 (2) | H8A—O8—H8B | 119.3 |
O5—C13—C8 | 115.97 (19) | | |
| | | |
O1—S1—O3—C8 | −172.61 (16) | C14—O5—C13—C8 | 171.5 (2) |
O2—S1—O3—C8 | −44.13 (19) | C11—C12—C13—O5 | −176.3 (2) |
C1—S1—O3—C8 | 72.82 (17) | C11—C12—C13—C8 | 1.0 (4) |
C15—N1—N2—C16 | 178.1 (2) | C9—C8—C13—O5 | 177.21 (19) |
O1—S1—C1—C6 | 150.9 (2) | O3—C8—C13—O5 | 3.6 (3) |
O2—S1—C1—C6 | 16.3 (2) | C9—C8—C13—C12 | −0.4 (4) |
O3—S1—C1—C6 | −100.2 (2) | O3—C8—C13—C12 | −174.0 (2) |
O1—S1—C1—C2 | −32.6 (2) | N2—N1—C15—C10 | 178.5 (2) |
O2—S1—C1—C2 | −167.14 (19) | C11—C10—C15—N1 | −179.4 (2) |
O3—S1—C1—C2 | 76.3 (2) | C9—C10—C15—N1 | −1.4 (4) |
C6—C1—C2—C3 | 1.4 (4) | N1—N2—C16—O4 | −3.4 (5) |
S1—C1—C2—C3 | −175.19 (19) | N1—N2—C16—C17 | 175.0 (2) |
C1—C2—C3—C4 | 0.3 (4) | O4—C16—C17—C18 | 6.8 (5) |
C2—C3—C4—C5 | −1.6 (4) | N2—C16—C17—C18 | −171.7 (3) |
C2—C3—C4—C7 | 178.7 (3) | O4—C16—C17—C22 | −174.3 (3) |
C3—C4—C5—C6 | 1.2 (4) | N2—C16—C17—C22 | 7.3 (5) |
C7—C4—C5—C6 | −179.1 (3) | C22—C17—C18—C19 | 0.1 (5) |
C4—C5—C6—C1 | 0.4 (4) | C16—C17—C18—C19 | 179.2 (3) |
C2—C1—C6—C5 | −1.7 (4) | C17—C18—C19—C20 | 0.5 (6) |
S1—C1—C6—C5 | 174.8 (2) | C18—C19—C20—C21 | 0.2 (6) |
S1—O3—C8—C9 | 87.9 (2) | C19—C20—C21—C22 | −1.3 (5) |
S1—O3—C8—C13 | −98.2 (2) | C23—O6—C22—C21 | −4.7 (4) |
C13—C8—C9—C10 | −0.5 (4) | C23—O6—C22—C17 | 174.2 (3) |
O3—C8—C9—C10 | 173.0 (2) | C20—C21—C22—O6 | −179.3 (3) |
C8—C9—C10—C11 | 0.8 (4) | C20—C21—C22—C17 | 1.8 (4) |
C8—C9—C10—C15 | −177.3 (2) | C18—C17—C22—O6 | 179.8 (3) |
C9—C10—C11—C12 | −0.1 (4) | C16—C17—C22—O6 | 0.9 (4) |
C15—C10—C11—C12 | 177.9 (2) | C18—C17—C22—C21 | −1.2 (4) |
C10—C11—C12—C13 | −0.8 (4) | C16—C17—C22—C21 | 179.8 (3) |
C14—O5—C13—C12 | −11.1 (4) | | |
Symmetry code: (i) −x+2, −y+1, −z+1. |
Hydrogen-bond geometry (Å, º) top
D—H···A | D—H | H···A | D···A | D—H···A |
N2—H2···O6 | 0.86 | 1.97 | 2.641 (3) | 134 |
O8—H8B···O4ii | 0.87 | 2.37 | 2.938 (11) | 124 |
O7—H7···O4ii | 0.82 | 2.39 | 2.814 (4) | 113 |
C15—H15···O8iii | 0.93 | 2.49 | 3.414 (8) | 172 |
C14—H14C···O1iv | 0.96 | 2.42 | 3.223 (4) | 141 |
Symmetry codes: (ii) x+1, y−1, z; (iii) x−1, y, z; (iv) x, y−1, z. |
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