The dihydropyrimidine ring adopts a twist-boat conformation while the quinone ring is slightly non-planar. In the crystal, molecules are linked by weak C—H

O and C—H

S hydrogen bonds and C—H

π interactions. In addition, a short intermolecular S

N contact occurs.
Supporting information
CCDC reference: 1814348
Key indicators
- Single-crystal X-ray study
- T = 293 K
- Mean
(C-C) = 0.005 Å
- R factor = 0.035
- wR factor = 0.087
- Data-to-parameter ratio = 12.7
checkCIF/PLATON results
No syntax errors found
Alert level C
PLAT089_ALERT_3_C Poor Data / Parameter Ratio (Zmax < 18) ........ 7.29 Note
PLAT340_ALERT_3_C Low Bond Precision on C-C Bonds ............... 0.00491 Ang.
PLAT910_ALERT_3_C Missing # of FCF Reflection(s) Below Theta(Min). 5 Note
Alert level G
PLAT199_ALERT_1_G Reported _cell_measurement_temperature ..... (K) 293 Check
PLAT200_ALERT_1_G Reported _diffrn_ambient_temperature ..... (K) 293 Check
PLAT333_ALERT_2_G Large Aver C6-Ring C-C Dist. C1 -C10 1.44 Ang.
PLAT791_ALERT_4_G Model has Chirality at C12 (Chiral SPGR) S Verify
PLAT850_ALERT_4_G Check Flack Parameter Exact Value 0.00 and s.u. 0.04 Check
PLAT909_ALERT_3_G Percentage of I>2sig(I) Data at Theta(Max) Still 70% Note
PLAT961_ALERT_5_G Dataset Contains no Negative Intensities ....... Please Check
PLAT978_ALERT_2_G Number C-C Bonds with Positive Residual Density. 1 Info
0 ALERT level A = Most likely a serious problem - resolve or explain
0 ALERT level B = A potentially serious problem, consider carefully
3 ALERT level C = Check. Ensure it is not caused by an omission or oversight
8 ALERT level G = General information/check it is not something unexpected
2 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
4 ALERT type 3 Indicator that the structure quality may be low
2 ALERT type 4 Improvement, methodology, query or suggestion
1 ALERT type 5 Informative message, check
Data collection: (CrysAlis PRO; Oxford Diffraction, 2010; cell refinement: (CrysAlis PRO; Oxford Diffraction, 2010; data reduction: (CrysAlis PRO; Oxford Diffraction, 2010; program(s) used to solve structure: SHELXT (Sheldrick, 2015a); program(s) used to refine structure: SHELXL2014/7 (Sheldrick, 2015b); molecular graphics: Mercury (Macrae et al., 2008); software used to prepare material for publication: publCIF (Westrip, 2010).
Ethyl 2-methyl-5,10-dioxo-4-phenyl-5,10-dihydro-4
H-11-thia-1,4a-\
diazabenzo[
b]fluorene-3-carboxylate
top
Crystal data top
C24H18N2O4S | Dx = 1.406 Mg m−3 |
Mr = 430.46 | Mo Kα radiation, λ = 0.71073 Å |
Orthorhombic, P212121 | Cell parameters from 3614 reflections |
a = 8.1038 (3) Å | θ = 3.0–29.0° |
b = 13.3915 (6) Å | µ = 0.19 mm−1 |
c = 18.7377 (9) Å | T = 293 K |
V = 2033.44 (15) Å3 | Block, red |
Z = 4 | 0.14 × 0.14 × 0.12 mm |
F(000) = 896 | |
Data collection top
Oxford Diffraction Xcalibur, Sapphire3 diffractometer | 3574 independent reflections |
Radiation source: Enhance (Mo) X-ray Source | 3160 reflections with I > 2σ(I) |
Detector resolution: 16.1827 pixels mm-1 | Rint = 0.017 |
ω–scan | θmax = 25.0°, θmin = 3.0° |
Absorption correction: multi-scan (CrysAlisPro; Oxford Diffraction, 2010 | h = −9→9 |
Tmin = 0.991, Tmax = 1.000 | k = −13→15 |
6202 measured reflections | l = −22→22 |
Refinement top
Refinement on F2 | Secondary atom site location: difference Fourier map |
Least-squares matrix: full | Hydrogen site location: inferred from neighbouring sites |
R[F2 > 2σ(F2)] = 0.035 | H-atom parameters constrained |
wR(F2) = 0.087 | w = 1/[σ2(Fo2) + (0.0436P)2 + 0.1932P] where P = (Fo2 + 2Fc2)/3 |
S = 1.03 | (Δ/σ)max < 0.001 |
3574 reflections | Δρmax = 0.13 e Å−3 |
282 parameters | Δρmin = −0.14 e Å−3 |
0 restraints | Absolute structure: Flack x determined using 1207 quotients
[(I+)-(I-)]/[(I+)+(I-)]
(Parsons et al., 2013). |
Primary atom site location: difference Fourier map | Absolute structure parameter: 0.00 (4) |
Special details top
Geometry. All esds (except the esd in the dihedral angle between two l.s. planes)
are estimated using the full covariance matrix. The cell esds are taken
into account individually in the estimation of esds in distances, angles
and torsion angles; correlations between esds in cell parameters are only
used when they are defined by crystal symmetry. An approximate (isotropic)
treatment of cell esds is used for estimating esds involving l.s. planes. |
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top | x | y | z | Uiso*/Ueq | |
S1 | 0.70278 (10) | 0.68425 (6) | 0.96988 (5) | 0.0577 (2) | |
O1 | 0.7487 (4) | 0.6165 (2) | 0.81545 (17) | 0.0925 (9) | |
O2 | 1.0119 (3) | 0.97193 (18) | 0.87923 (13) | 0.0727 (7) | |
O3 | 1.0162 (4) | 1.08986 (18) | 1.09805 (13) | 0.0801 (8) | |
O4 | 0.9283 (2) | 1.03242 (17) | 1.20226 (11) | 0.0561 (6) | |
N1 | 0.8225 (3) | 0.86059 (16) | 0.98532 (12) | 0.0414 (5) | |
N2 | 0.7164 (3) | 0.78761 (17) | 1.09161 (14) | 0.0499 (6) | |
C1 | 0.9415 (4) | 0.8572 (3) | 0.78826 (16) | 0.0527 (8) | |
C2 | 1.0157 (4) | 0.9143 (3) | 0.73617 (18) | 0.0670 (10) | |
H2 | 1.0638 | 0.9752 | 0.7478 | 0.080* | |
C3 | 1.0179 (5) | 0.8804 (4) | 0.6664 (2) | 0.0827 (12) | |
H3 | 1.0673 | 0.9191 | 0.6311 | 0.099* | |
C4 | 0.9489 (5) | 0.7914 (4) | 0.6487 (2) | 0.0890 (14) | |
H4 | 0.9493 | 0.7704 | 0.6014 | 0.107* | |
C5 | 0.8785 (5) | 0.7318 (4) | 0.7004 (2) | 0.0766 (11) | |
H5 | 0.8338 | 0.6701 | 0.6881 | 0.092* | |
C6 | 0.8745 (4) | 0.7644 (3) | 0.77107 (18) | 0.0589 (9) | |
C7 | 0.8000 (4) | 0.7003 (3) | 0.82700 (19) | 0.0604 (8) | |
C8 | 0.7887 (4) | 0.7446 (2) | 0.89746 (17) | 0.0497 (7) | |
C9 | 0.8483 (3) | 0.8355 (2) | 0.91469 (16) | 0.0428 (7) | |
C10 | 0.9400 (4) | 0.8963 (2) | 0.86233 (17) | 0.0499 (7) | |
C11 | 0.7472 (3) | 0.7863 (2) | 1.02436 (18) | 0.0450 (7) | |
C12 | 0.8429 (3) | 0.96026 (19) | 1.01698 (15) | 0.0415 (6) | |
H12 | 0.9494 | 0.9872 | 1.0014 | 0.050* | |
C13 | 0.8477 (3) | 0.9481 (2) | 1.09764 (15) | 0.0415 (6) | |
C14 | 0.7823 (3) | 0.8678 (2) | 1.13005 (16) | 0.0446 (7) | |
C15 | 0.7081 (4) | 1.0300 (2) | 0.99115 (14) | 0.0438 (6) | |
C16 | 0.5438 (4) | 1.0063 (3) | 0.99771 (17) | 0.0565 (8) | |
H16 | 0.5133 | 0.9456 | 1.0179 | 0.068* | |
C17 | 0.4239 (5) | 1.0717 (3) | 0.9747 (2) | 0.0722 (10) | |
H17 | 0.3131 | 1.0548 | 0.9792 | 0.087* | |
C18 | 0.4674 (6) | 1.1617 (3) | 0.9451 (2) | 0.0774 (11) | |
H18 | 0.3864 | 1.2060 | 0.9298 | 0.093* | |
C19 | 0.6310 (6) | 1.1857 (3) | 0.9383 (2) | 0.0832 (12) | |
H19 | 0.6611 | 1.2466 | 0.9183 | 0.100* | |
C20 | 0.7504 (5) | 1.1206 (2) | 0.9608 (2) | 0.0660 (9) | |
H20 | 0.8611 | 1.1374 | 0.9556 | 0.079* | |
C21 | 0.9387 (4) | 1.0299 (2) | 1.13135 (16) | 0.0471 (7) | |
C22 | 1.0268 (4) | 1.1067 (3) | 1.23806 (18) | 0.0609 (9) | |
H22B | 0.9735 | 1.1714 | 1.2355 | 0.073* | |
H22A | 1.1346 | 1.1117 | 1.2158 | 0.073* | |
C23 | 1.0436 (5) | 1.0742 (3) | 1.3141 (2) | 0.0815 (12) | |
H23B | 0.9359 | 1.0665 | 1.3348 | 0.122* | |
H23C | 1.1043 | 1.1236 | 1.3403 | 0.122* | |
H23A | 1.1012 | 1.0116 | 1.3160 | 0.122* | |
C24 | 0.7765 (4) | 0.8499 (2) | 1.20923 (17) | 0.0594 (8) | |
H24C | 0.8858 | 0.8554 | 1.2287 | 0.089* | |
H24A | 0.7341 | 0.7842 | 1.2184 | 0.089* | |
H24B | 0.7061 | 0.8986 | 1.2312 | 0.089* | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
S1 | 0.0570 (4) | 0.0437 (4) | 0.0725 (5) | −0.0110 (4) | 0.0073 (4) | −0.0060 (4) |
O1 | 0.105 (2) | 0.0743 (17) | 0.098 (2) | −0.0213 (16) | 0.0155 (17) | −0.0383 (17) |
O2 | 0.0955 (17) | 0.0606 (14) | 0.0620 (14) | −0.0237 (14) | 0.0224 (14) | −0.0034 (13) |
O3 | 0.121 (2) | 0.0638 (14) | 0.0554 (13) | −0.0474 (16) | −0.0102 (15) | 0.0097 (13) |
O4 | 0.0569 (13) | 0.0627 (13) | 0.0486 (11) | −0.0122 (11) | −0.0002 (10) | −0.0033 (11) |
N1 | 0.0428 (12) | 0.0360 (12) | 0.0452 (13) | −0.0025 (10) | 0.0018 (11) | 0.0033 (11) |
N2 | 0.0532 (14) | 0.0423 (13) | 0.0542 (15) | −0.0095 (12) | 0.0019 (13) | 0.0078 (12) |
C1 | 0.0458 (16) | 0.064 (2) | 0.0482 (17) | 0.0134 (15) | −0.0009 (14) | −0.0004 (16) |
C2 | 0.065 (2) | 0.082 (3) | 0.0540 (19) | 0.0140 (19) | 0.0023 (18) | 0.007 (2) |
C3 | 0.082 (3) | 0.115 (4) | 0.051 (2) | 0.020 (3) | 0.001 (2) | 0.009 (2) |
C4 | 0.080 (3) | 0.140 (4) | 0.047 (2) | 0.022 (3) | −0.003 (2) | −0.012 (3) |
C5 | 0.069 (2) | 0.096 (3) | 0.065 (2) | 0.015 (2) | −0.008 (2) | −0.024 (2) |
C6 | 0.0482 (17) | 0.073 (2) | 0.0555 (19) | 0.0138 (16) | −0.0033 (16) | −0.0110 (18) |
C7 | 0.0503 (16) | 0.060 (2) | 0.071 (2) | 0.0030 (17) | 0.0007 (17) | −0.0185 (18) |
C8 | 0.0419 (15) | 0.0473 (16) | 0.0598 (18) | 0.0009 (14) | 0.0013 (15) | −0.0053 (15) |
C9 | 0.0374 (13) | 0.0410 (16) | 0.0501 (16) | 0.0042 (11) | −0.0016 (12) | −0.0006 (14) |
C10 | 0.0487 (17) | 0.0497 (18) | 0.0514 (17) | 0.0037 (15) | 0.0036 (14) | 0.0034 (15) |
C11 | 0.0373 (14) | 0.0371 (15) | 0.0605 (19) | −0.0037 (11) | 0.0011 (13) | 0.0068 (15) |
C12 | 0.0478 (15) | 0.0309 (13) | 0.0458 (15) | −0.0033 (11) | 0.0024 (12) | 0.0032 (13) |
C13 | 0.0421 (14) | 0.0383 (14) | 0.0441 (15) | −0.0003 (12) | −0.0025 (12) | 0.0044 (13) |
C14 | 0.0417 (14) | 0.0446 (15) | 0.0475 (16) | −0.0003 (13) | 0.0005 (14) | 0.0079 (14) |
C15 | 0.0537 (16) | 0.0373 (15) | 0.0405 (14) | 0.0042 (13) | −0.0029 (13) | 0.0013 (12) |
C16 | 0.0561 (18) | 0.0533 (17) | 0.0600 (18) | 0.0068 (15) | −0.0048 (15) | 0.0014 (16) |
C17 | 0.063 (2) | 0.081 (3) | 0.072 (2) | 0.0174 (19) | −0.014 (2) | −0.007 (2) |
C18 | 0.099 (3) | 0.068 (2) | 0.065 (2) | 0.037 (2) | −0.022 (2) | −0.001 (2) |
C19 | 0.107 (3) | 0.056 (2) | 0.087 (3) | 0.019 (2) | −0.009 (3) | 0.020 (2) |
C20 | 0.074 (2) | 0.0463 (18) | 0.078 (2) | 0.0044 (15) | −0.0003 (19) | 0.0149 (18) |
C21 | 0.0526 (16) | 0.0405 (16) | 0.0482 (16) | −0.0021 (14) | −0.0042 (14) | 0.0065 (15) |
C22 | 0.062 (2) | 0.062 (2) | 0.0587 (19) | −0.0050 (17) | −0.0081 (17) | −0.0109 (17) |
C23 | 0.085 (3) | 0.101 (3) | 0.058 (2) | −0.009 (2) | −0.004 (2) | −0.010 (2) |
C24 | 0.071 (2) | 0.0556 (18) | 0.0518 (18) | −0.0078 (16) | 0.0021 (17) | 0.0139 (16) |
Geometric parameters (Å, º) top
S1—C8 | 1.726 (3) | C12—C15 | 1.517 (4) |
S1—C11 | 1.743 (3) | C12—C13 | 1.521 (4) |
O1—C7 | 1.216 (4) | C12—H12 | 0.9800 |
O2—C10 | 1.211 (4) | C13—C14 | 1.344 (4) |
O3—C21 | 1.195 (3) | C13—C21 | 1.463 (4) |
O4—C21 | 1.332 (4) | C14—C24 | 1.504 (4) |
O4—C22 | 1.441 (4) | C15—C16 | 1.374 (4) |
N1—C11 | 1.378 (3) | C15—C20 | 1.383 (4) |
N1—C9 | 1.381 (4) | C16—C17 | 1.377 (4) |
N1—C12 | 1.470 (4) | C16—H16 | 0.9300 |
N2—C11 | 1.285 (4) | C17—C18 | 1.373 (6) |
N2—C14 | 1.399 (4) | C17—H17 | 0.9300 |
C1—C2 | 1.378 (5) | C18—C19 | 1.371 (6) |
C1—C6 | 1.394 (5) | C18—H18 | 0.9300 |
C1—C10 | 1.484 (4) | C19—C20 | 1.369 (5) |
C2—C3 | 1.384 (5) | C19—H19 | 0.9300 |
C2—H2 | 0.9300 | C20—H20 | 0.9300 |
C3—C4 | 1.358 (6) | C22—C23 | 1.497 (5) |
C3—H3 | 0.9300 | C22—H22B | 0.9700 |
C4—C5 | 1.378 (6) | C22—H22A | 0.9700 |
C4—H4 | 0.9300 | C23—H23B | 0.9600 |
C5—C6 | 1.395 (5) | C23—H23C | 0.9600 |
C5—H5 | 0.9300 | C23—H23A | 0.9600 |
C6—C7 | 1.483 (5) | C24—H24C | 0.9600 |
C7—C8 | 1.451 (5) | C24—H24A | 0.9600 |
C8—C9 | 1.348 (4) | C24—H24B | 0.9600 |
C9—C10 | 1.476 (4) | | |
| | | |
C8—S1—C11 | 90.57 (14) | C14—C13—C21 | 127.1 (3) |
C21—O4—C22 | 116.5 (2) | C14—C13—C12 | 121.6 (3) |
C11—N1—C9 | 113.6 (2) | C21—C13—C12 | 111.2 (2) |
C11—N1—C12 | 119.4 (2) | C13—C14—N2 | 122.2 (3) |
C9—N1—C12 | 126.2 (2) | C13—C14—C24 | 125.9 (3) |
C11—N2—C14 | 116.2 (2) | N2—C14—C24 | 111.9 (3) |
C2—C1—C6 | 120.1 (3) | C16—C15—C20 | 118.7 (3) |
C2—C1—C10 | 118.0 (3) | C16—C15—C12 | 121.8 (3) |
C6—C1—C10 | 121.9 (3) | C20—C15—C12 | 119.5 (3) |
C1—C2—C3 | 119.5 (4) | C15—C16—C17 | 120.6 (3) |
C1—C2—H2 | 120.3 | C15—C16—H16 | 119.7 |
C3—C2—H2 | 120.3 | C17—C16—H16 | 119.7 |
C4—C3—C2 | 120.8 (4) | C18—C17—C16 | 120.2 (4) |
C4—C3—H3 | 119.6 | C18—C17—H17 | 119.9 |
C2—C3—H3 | 119.6 | C16—C17—H17 | 119.9 |
C3—C4—C5 | 120.5 (4) | C19—C18—C17 | 119.5 (3) |
C3—C4—H4 | 119.7 | C19—C18—H18 | 120.3 |
C5—C4—H4 | 119.7 | C17—C18—H18 | 120.3 |
C4—C5—C6 | 119.7 (4) | C20—C19—C18 | 120.4 (4) |
C4—C5—H5 | 120.2 | C20—C19—H19 | 119.8 |
C6—C5—H5 | 120.2 | C18—C19—H19 | 119.8 |
C1—C6—C5 | 119.3 (4) | C19—C20—C15 | 120.7 (4) |
C1—C6—C7 | 120.7 (3) | C19—C20—H20 | 119.7 |
C5—C6—C7 | 120.0 (4) | C15—C20—H20 | 119.7 |
O1—C7—C8 | 121.2 (3) | O3—C21—O4 | 122.5 (3) |
O1—C7—C6 | 123.2 (3) | O3—C21—C13 | 122.8 (3) |
C8—C7—C6 | 115.6 (3) | O4—C21—C13 | 114.7 (3) |
C9—C8—C7 | 124.4 (3) | O4—C22—C23 | 107.0 (3) |
C9—C8—S1 | 112.3 (2) | O4—C22—H22B | 110.3 |
C7—C8—S1 | 123.3 (2) | C23—C22—H22B | 110.3 |
C8—C9—N1 | 113.3 (3) | O4—C22—H22A | 110.3 |
C8—C9—C10 | 121.3 (3) | C23—C22—H22A | 110.3 |
N1—C9—C10 | 125.4 (3) | H22B—C22—H22A | 108.6 |
O2—C10—C9 | 122.0 (3) | C22—C23—H23B | 109.5 |
O2—C10—C1 | 122.4 (3) | C22—C23—H23C | 109.5 |
C9—C10—C1 | 115.5 (3) | H23B—C23—H23C | 109.5 |
N2—C11—N1 | 126.6 (3) | C22—C23—H23A | 109.5 |
N2—C11—S1 | 123.1 (2) | H23B—C23—H23A | 109.5 |
N1—C11—S1 | 110.3 (2) | H23C—C23—H23A | 109.5 |
N1—C12—C15 | 110.4 (2) | C14—C24—H24C | 109.5 |
N1—C12—C13 | 107.9 (2) | C14—C24—H24A | 109.5 |
C15—C12—C13 | 113.7 (2) | H24C—C24—H24A | 109.5 |
N1—C12—H12 | 108.2 | C14—C24—H24B | 109.5 |
C15—C12—H12 | 108.2 | H24C—C24—H24B | 109.5 |
C13—C12—H12 | 108.2 | H24A—C24—H24B | 109.5 |
| | | |
C6—C1—C2—C3 | 2.3 (5) | C9—N1—C11—N2 | 176.2 (3) |
C10—C1—C2—C3 | −179.4 (3) | C12—N1—C11—N2 | −13.3 (4) |
C1—C2—C3—C4 | −0.4 (6) | C9—N1—C11—S1 | −1.8 (3) |
C2—C3—C4—C5 | −1.5 (6) | C12—N1—C11—S1 | 168.65 (19) |
C3—C4—C5—C6 | 1.6 (6) | C8—S1—C11—N2 | −177.5 (3) |
C2—C1—C6—C5 | −2.2 (5) | C8—S1—C11—N1 | 0.6 (2) |
C10—C1—C6—C5 | 179.6 (3) | C11—N1—C12—C15 | −98.7 (3) |
C2—C1—C6—C7 | 177.6 (3) | C9—N1—C12—C15 | 70.4 (3) |
C10—C1—C6—C7 | −0.6 (4) | C11—N1—C12—C13 | 26.1 (3) |
C4—C5—C6—C1 | 0.3 (5) | C9—N1—C12—C13 | −164.8 (2) |
C4—C5—C6—C7 | −179.5 (3) | N1—C12—C13—C14 | −22.3 (4) |
C1—C6—C7—O1 | −175.6 (3) | C15—C12—C13—C14 | 100.5 (3) |
C5—C6—C7—O1 | 4.2 (5) | N1—C12—C13—C21 | 154.3 (2) |
C1—C6—C7—C8 | 5.5 (4) | C15—C12—C13—C21 | −82.9 (3) |
C5—C6—C7—C8 | −174.7 (3) | C21—C13—C14—N2 | −171.5 (3) |
O1—C7—C8—C9 | 177.5 (3) | C12—C13—C14—N2 | 4.5 (4) |
C6—C7—C8—C9 | −3.6 (5) | C21—C13—C14—C24 | 5.7 (5) |
O1—C7—C8—S1 | −0.2 (5) | C12—C13—C14—C24 | −178.3 (3) |
C6—C7—C8—S1 | 178.7 (2) | C11—N2—C14—C13 | 11.8 (4) |
C11—S1—C8—C9 | 0.7 (2) | C11—N2—C14—C24 | −165.7 (3) |
C11—S1—C8—C7 | 178.6 (3) | N1—C12—C15—C16 | 54.1 (4) |
C7—C8—C9—N1 | −179.8 (3) | C13—C12—C15—C16 | −67.3 (4) |
S1—C8—C9—N1 | −1.9 (3) | N1—C12—C15—C20 | −126.6 (3) |
C7—C8—C9—C10 | −3.3 (4) | C13—C12—C15—C20 | 112.0 (3) |
S1—C8—C9—C10 | 174.6 (2) | C20—C15—C16—C17 | −0.2 (5) |
C11—N1—C9—C8 | 2.4 (3) | C12—C15—C16—C17 | 179.1 (3) |
C12—N1—C9—C8 | −167.3 (3) | C15—C16—C17—C18 | −0.2 (5) |
C11—N1—C9—C10 | −173.9 (2) | C16—C17—C18—C19 | 0.4 (6) |
C12—N1—C9—C10 | 16.4 (4) | C17—C18—C19—C20 | 0.0 (7) |
C8—C9—C10—O2 | −170.5 (3) | C18—C19—C20—C15 | −0.4 (6) |
N1—C9—C10—O2 | 5.5 (5) | C16—C15—C20—C19 | 0.5 (5) |
C8—C9—C10—C1 | 8.0 (4) | C12—C15—C20—C19 | −178.8 (3) |
N1—C9—C10—C1 | −175.9 (3) | C22—O4—C21—O3 | −5.1 (5) |
C2—C1—C10—O2 | −5.8 (5) | C22—O4—C21—C13 | 175.1 (2) |
C6—C1—C10—O2 | 172.5 (3) | C14—C13—C21—O3 | 167.2 (3) |
C2—C1—C10—C9 | 175.7 (3) | C12—C13—C21—O3 | −9.1 (4) |
C6—C1—C10—C9 | −6.1 (4) | C14—C13—C21—O4 | −12.9 (4) |
C14—N2—C11—N1 | −7.6 (4) | C12—C13—C21—O4 | 170.8 (2) |
C14—N2—C11—S1 | 170.2 (2) | C21—O4—C22—C23 | −160.5 (3) |
Hydrogen-bond geometry (Å, º) top
D—H···A | D—H | H···A | D···A | D—H···A |
C12—H12···O2 | 0.98 | 2.36 | 2.926 (4) | 116 |
C19—H19···O3i | 0.93 | 2.50 | 3.219 (5) | 134 |
C16—H16···S1ii | 0.93 | 3.07 | 3.810 (4) | 138 |
C3—H3···C16iii | 0.93 | 2.84 | 3.542 (5) | 133 |
C22—H22A···C2iv | 0.97 | 2.88 | 3.718 (5) | 145 |
Symmetry codes: (i) x−1/2, −y+5/2, −z+2; (ii) x−1/2, −y+3/2, −z+2; (iii) −x+3/2, −y+2, z−1/2; (iv) −x+5/2, −y+2, z+1/2. |