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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

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S2056989018000117/zq2240sup1.cif
Contains datablock I

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S2056989018000117/zq2240Isup2.hkl
Contains datablock I

CCDC reference: 1814348

Key indicators

  • Single-crystal X-ray study
  • T = 293 K
  • Mean [sigma](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

Computing details top

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-4H-11-thia-1,4a-\ diazabenzo[b]fluorene-3-carboxylate top
Crystal data top
C24H18N2O4SDx = 1.406 Mg m3
Mr = 430.46Mo Kα radiation, λ = 0.71073 Å
Orthorhombic, P212121Cell parameters from 3614 reflections
a = 8.1038 (3) Åθ = 3.0–29.0°
b = 13.3915 (6) ŵ = 0.19 mm1
c = 18.7377 (9) ÅT = 293 K
V = 2033.44 (15) Å3Block, red
Z = 40.14 × 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 Source3160 reflections with I > 2σ(I)
Detector resolution: 16.1827 pixels mm-1Rint = 0.017
ω–scanθmax = 25.0°, θmin = 3.0°
Absorption correction: multi-scan
(CrysAlisPro; Oxford Diffraction, 2010
h = 99
Tmin = 0.991, Tmax = 1.000k = 1315
6202 measured reflectionsl = 2222
Refinement top
Refinement on F2Secondary atom site location: difference Fourier map
Least-squares matrix: fullHydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.035H-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 reflectionsΔρmax = 0.13 e Å3
282 parametersΔρmin = 0.14 e Å3
0 restraintsAbsolute structure: Flack x determined using 1207 quotients [(I+)-(I-)]/[(I+)+(I-)] (Parsons et al., 2013).
Primary atom site location: difference Fourier mapAbsolute 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
xyzUiso*/Ueq
S10.70278 (10)0.68425 (6)0.96988 (5)0.0577 (2)
O10.7487 (4)0.6165 (2)0.81545 (17)0.0925 (9)
O21.0119 (3)0.97193 (18)0.87923 (13)0.0727 (7)
O31.0162 (4)1.08986 (18)1.09805 (13)0.0801 (8)
O40.9283 (2)1.03242 (17)1.20226 (11)0.0561 (6)
N10.8225 (3)0.86059 (16)0.98532 (12)0.0414 (5)
N20.7164 (3)0.78761 (17)1.09161 (14)0.0499 (6)
C10.9415 (4)0.8572 (3)0.78826 (16)0.0527 (8)
C21.0157 (4)0.9143 (3)0.73617 (18)0.0670 (10)
H21.06380.97520.74780.080*
C31.0179 (5)0.8804 (4)0.6664 (2)0.0827 (12)
H31.06730.91910.63110.099*
C40.9489 (5)0.7914 (4)0.6487 (2)0.0890 (14)
H40.94930.77040.60140.107*
C50.8785 (5)0.7318 (4)0.7004 (2)0.0766 (11)
H50.83380.67010.68810.092*
C60.8745 (4)0.7644 (3)0.77107 (18)0.0589 (9)
C70.8000 (4)0.7003 (3)0.82700 (19)0.0604 (8)
C80.7887 (4)0.7446 (2)0.89746 (17)0.0497 (7)
C90.8483 (3)0.8355 (2)0.91469 (16)0.0428 (7)
C100.9400 (4)0.8963 (2)0.86233 (17)0.0499 (7)
C110.7472 (3)0.7863 (2)1.02436 (18)0.0450 (7)
C120.8429 (3)0.96026 (19)1.01698 (15)0.0415 (6)
H120.94940.98721.00140.050*
C130.8477 (3)0.9481 (2)1.09764 (15)0.0415 (6)
C140.7823 (3)0.8678 (2)1.13005 (16)0.0446 (7)
C150.7081 (4)1.0300 (2)0.99115 (14)0.0438 (6)
C160.5438 (4)1.0063 (3)0.99771 (17)0.0565 (8)
H160.51330.94561.01790.068*
C170.4239 (5)1.0717 (3)0.9747 (2)0.0722 (10)
H170.31311.05480.97920.087*
C180.4674 (6)1.1617 (3)0.9451 (2)0.0774 (11)
H180.38641.20600.92980.093*
C190.6310 (6)1.1857 (3)0.9383 (2)0.0832 (12)
H190.66111.24660.91830.100*
C200.7504 (5)1.1206 (2)0.9608 (2)0.0660 (9)
H200.86111.13740.95560.079*
C210.9387 (4)1.0299 (2)1.13135 (16)0.0471 (7)
C221.0268 (4)1.1067 (3)1.23806 (18)0.0609 (9)
H22B0.97351.17141.23550.073*
H22A1.13461.11171.21580.073*
C231.0436 (5)1.0742 (3)1.3141 (2)0.0815 (12)
H23B0.93591.06651.33480.122*
H23C1.10431.12361.34030.122*
H23A1.10121.01161.31600.122*
C240.7765 (4)0.8499 (2)1.20923 (17)0.0594 (8)
H24C0.88580.85541.22870.089*
H24A0.73410.78421.21840.089*
H24B0.70610.89861.23120.089*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
S10.0570 (4)0.0437 (4)0.0725 (5)0.0110 (4)0.0073 (4)0.0060 (4)
O10.105 (2)0.0743 (17)0.098 (2)0.0213 (16)0.0155 (17)0.0383 (17)
O20.0955 (17)0.0606 (14)0.0620 (14)0.0237 (14)0.0224 (14)0.0034 (13)
O30.121 (2)0.0638 (14)0.0554 (13)0.0474 (16)0.0102 (15)0.0097 (13)
O40.0569 (13)0.0627 (13)0.0486 (11)0.0122 (11)0.0002 (10)0.0033 (11)
N10.0428 (12)0.0360 (12)0.0452 (13)0.0025 (10)0.0018 (11)0.0033 (11)
N20.0532 (14)0.0423 (13)0.0542 (15)0.0095 (12)0.0019 (13)0.0078 (12)
C10.0458 (16)0.064 (2)0.0482 (17)0.0134 (15)0.0009 (14)0.0004 (16)
C20.065 (2)0.082 (3)0.0540 (19)0.0140 (19)0.0023 (18)0.007 (2)
C30.082 (3)0.115 (4)0.051 (2)0.020 (3)0.001 (2)0.009 (2)
C40.080 (3)0.140 (4)0.047 (2)0.022 (3)0.003 (2)0.012 (3)
C50.069 (2)0.096 (3)0.065 (2)0.015 (2)0.008 (2)0.024 (2)
C60.0482 (17)0.073 (2)0.0555 (19)0.0138 (16)0.0033 (16)0.0110 (18)
C70.0503 (16)0.060 (2)0.071 (2)0.0030 (17)0.0007 (17)0.0185 (18)
C80.0419 (15)0.0473 (16)0.0598 (18)0.0009 (14)0.0013 (15)0.0053 (15)
C90.0374 (13)0.0410 (16)0.0501 (16)0.0042 (11)0.0016 (12)0.0006 (14)
C100.0487 (17)0.0497 (18)0.0514 (17)0.0037 (15)0.0036 (14)0.0034 (15)
C110.0373 (14)0.0371 (15)0.0605 (19)0.0037 (11)0.0011 (13)0.0068 (15)
C120.0478 (15)0.0309 (13)0.0458 (15)0.0033 (11)0.0024 (12)0.0032 (13)
C130.0421 (14)0.0383 (14)0.0441 (15)0.0003 (12)0.0025 (12)0.0044 (13)
C140.0417 (14)0.0446 (15)0.0475 (16)0.0003 (13)0.0005 (14)0.0079 (14)
C150.0537 (16)0.0373 (15)0.0405 (14)0.0042 (13)0.0029 (13)0.0013 (12)
C160.0561 (18)0.0533 (17)0.0600 (18)0.0068 (15)0.0048 (15)0.0014 (16)
C170.063 (2)0.081 (3)0.072 (2)0.0174 (19)0.014 (2)0.007 (2)
C180.099 (3)0.068 (2)0.065 (2)0.037 (2)0.022 (2)0.001 (2)
C190.107 (3)0.056 (2)0.087 (3)0.019 (2)0.009 (3)0.020 (2)
C200.074 (2)0.0463 (18)0.078 (2)0.0044 (15)0.0003 (19)0.0149 (18)
C210.0526 (16)0.0405 (16)0.0482 (16)0.0021 (14)0.0042 (14)0.0065 (15)
C220.062 (2)0.062 (2)0.0587 (19)0.0050 (17)0.0081 (17)0.0109 (17)
C230.085 (3)0.101 (3)0.058 (2)0.009 (2)0.004 (2)0.010 (2)
C240.071 (2)0.0556 (18)0.0518 (18)0.0078 (16)0.0021 (17)0.0139 (16)
Geometric parameters (Å, º) top
S1—C81.726 (3)C12—C151.517 (4)
S1—C111.743 (3)C12—C131.521 (4)
O1—C71.216 (4)C12—H120.9800
O2—C101.211 (4)C13—C141.344 (4)
O3—C211.195 (3)C13—C211.463 (4)
O4—C211.332 (4)C14—C241.504 (4)
O4—C221.441 (4)C15—C161.374 (4)
N1—C111.378 (3)C15—C201.383 (4)
N1—C91.381 (4)C16—C171.377 (4)
N1—C121.470 (4)C16—H160.9300
N2—C111.285 (4)C17—C181.373 (6)
N2—C141.399 (4)C17—H170.9300
C1—C21.378 (5)C18—C191.371 (6)
C1—C61.394 (5)C18—H180.9300
C1—C101.484 (4)C19—C201.369 (5)
C2—C31.384 (5)C19—H190.9300
C2—H20.9300C20—H200.9300
C3—C41.358 (6)C22—C231.497 (5)
C3—H30.9300C22—H22B0.9700
C4—C51.378 (6)C22—H22A0.9700
C4—H40.9300C23—H23B0.9600
C5—C61.395 (5)C23—H23C0.9600
C5—H50.9300C23—H23A0.9600
C6—C71.483 (5)C24—H24C0.9600
C7—C81.451 (5)C24—H24A0.9600
C8—C91.348 (4)C24—H24B0.9600
C9—C101.476 (4)
C8—S1—C1190.57 (14)C14—C13—C21127.1 (3)
C21—O4—C22116.5 (2)C14—C13—C12121.6 (3)
C11—N1—C9113.6 (2)C21—C13—C12111.2 (2)
C11—N1—C12119.4 (2)C13—C14—N2122.2 (3)
C9—N1—C12126.2 (2)C13—C14—C24125.9 (3)
C11—N2—C14116.2 (2)N2—C14—C24111.9 (3)
C2—C1—C6120.1 (3)C16—C15—C20118.7 (3)
C2—C1—C10118.0 (3)C16—C15—C12121.8 (3)
C6—C1—C10121.9 (3)C20—C15—C12119.5 (3)
C1—C2—C3119.5 (4)C15—C16—C17120.6 (3)
C1—C2—H2120.3C15—C16—H16119.7
C3—C2—H2120.3C17—C16—H16119.7
C4—C3—C2120.8 (4)C18—C17—C16120.2 (4)
C4—C3—H3119.6C18—C17—H17119.9
C2—C3—H3119.6C16—C17—H17119.9
C3—C4—C5120.5 (4)C19—C18—C17119.5 (3)
C3—C4—H4119.7C19—C18—H18120.3
C5—C4—H4119.7C17—C18—H18120.3
C4—C5—C6119.7 (4)C20—C19—C18120.4 (4)
C4—C5—H5120.2C20—C19—H19119.8
C6—C5—H5120.2C18—C19—H19119.8
C1—C6—C5119.3 (4)C19—C20—C15120.7 (4)
C1—C6—C7120.7 (3)C19—C20—H20119.7
C5—C6—C7120.0 (4)C15—C20—H20119.7
O1—C7—C8121.2 (3)O3—C21—O4122.5 (3)
O1—C7—C6123.2 (3)O3—C21—C13122.8 (3)
C8—C7—C6115.6 (3)O4—C21—C13114.7 (3)
C9—C8—C7124.4 (3)O4—C22—C23107.0 (3)
C9—C8—S1112.3 (2)O4—C22—H22B110.3
C7—C8—S1123.3 (2)C23—C22—H22B110.3
C8—C9—N1113.3 (3)O4—C22—H22A110.3
C8—C9—C10121.3 (3)C23—C22—H22A110.3
N1—C9—C10125.4 (3)H22B—C22—H22A108.6
O2—C10—C9122.0 (3)C22—C23—H23B109.5
O2—C10—C1122.4 (3)C22—C23—H23C109.5
C9—C10—C1115.5 (3)H23B—C23—H23C109.5
N2—C11—N1126.6 (3)C22—C23—H23A109.5
N2—C11—S1123.1 (2)H23B—C23—H23A109.5
N1—C11—S1110.3 (2)H23C—C23—H23A109.5
N1—C12—C15110.4 (2)C14—C24—H24C109.5
N1—C12—C13107.9 (2)C14—C24—H24A109.5
C15—C12—C13113.7 (2)H24C—C24—H24A109.5
N1—C12—H12108.2C14—C24—H24B109.5
C15—C12—H12108.2H24C—C24—H24B109.5
C13—C12—H12108.2H24A—C24—H24B109.5
C6—C1—C2—C32.3 (5)C9—N1—C11—N2176.2 (3)
C10—C1—C2—C3179.4 (3)C12—N1—C11—N213.3 (4)
C1—C2—C3—C40.4 (6)C9—N1—C11—S11.8 (3)
C2—C3—C4—C51.5 (6)C12—N1—C11—S1168.65 (19)
C3—C4—C5—C61.6 (6)C8—S1—C11—N2177.5 (3)
C2—C1—C6—C52.2 (5)C8—S1—C11—N10.6 (2)
C10—C1—C6—C5179.6 (3)C11—N1—C12—C1598.7 (3)
C2—C1—C6—C7177.6 (3)C9—N1—C12—C1570.4 (3)
C10—C1—C6—C70.6 (4)C11—N1—C12—C1326.1 (3)
C4—C5—C6—C10.3 (5)C9—N1—C12—C13164.8 (2)
C4—C5—C6—C7179.5 (3)N1—C12—C13—C1422.3 (4)
C1—C6—C7—O1175.6 (3)C15—C12—C13—C14100.5 (3)
C5—C6—C7—O14.2 (5)N1—C12—C13—C21154.3 (2)
C1—C6—C7—C85.5 (4)C15—C12—C13—C2182.9 (3)
C5—C6—C7—C8174.7 (3)C21—C13—C14—N2171.5 (3)
O1—C7—C8—C9177.5 (3)C12—C13—C14—N24.5 (4)
C6—C7—C8—C93.6 (5)C21—C13—C14—C245.7 (5)
O1—C7—C8—S10.2 (5)C12—C13—C14—C24178.3 (3)
C6—C7—C8—S1178.7 (2)C11—N2—C14—C1311.8 (4)
C11—S1—C8—C90.7 (2)C11—N2—C14—C24165.7 (3)
C11—S1—C8—C7178.6 (3)N1—C12—C15—C1654.1 (4)
C7—C8—C9—N1179.8 (3)C13—C12—C15—C1667.3 (4)
S1—C8—C9—N11.9 (3)N1—C12—C15—C20126.6 (3)
C7—C8—C9—C103.3 (4)C13—C12—C15—C20112.0 (3)
S1—C8—C9—C10174.6 (2)C20—C15—C16—C170.2 (5)
C11—N1—C9—C82.4 (3)C12—C15—C16—C17179.1 (3)
C12—N1—C9—C8167.3 (3)C15—C16—C17—C180.2 (5)
C11—N1—C9—C10173.9 (2)C16—C17—C18—C190.4 (6)
C12—N1—C9—C1016.4 (4)C17—C18—C19—C200.0 (7)
C8—C9—C10—O2170.5 (3)C18—C19—C20—C150.4 (6)
N1—C9—C10—O25.5 (5)C16—C15—C20—C190.5 (5)
C8—C9—C10—C18.0 (4)C12—C15—C20—C19178.8 (3)
N1—C9—C10—C1175.9 (3)C22—O4—C21—O35.1 (5)
C2—C1—C10—O25.8 (5)C22—O4—C21—C13175.1 (2)
C6—C1—C10—O2172.5 (3)C14—C13—C21—O3167.2 (3)
C2—C1—C10—C9175.7 (3)C12—C13—C21—O39.1 (4)
C6—C1—C10—C96.1 (4)C14—C13—C21—O412.9 (4)
C14—N2—C11—N17.6 (4)C12—C13—C21—O4170.8 (2)
C14—N2—C11—S1170.2 (2)C21—O4—C22—C23160.5 (3)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
C12—H12···O20.982.362.926 (4)116
C19—H19···O3i0.932.503.219 (5)134
C16—H16···S1ii0.933.073.810 (4)138
C3—H3···C16iii0.932.843.542 (5)133
C22—H22A···C2iv0.972.883.718 (5)145
Symmetry codes: (i) x1/2, y+5/2, z+2; (ii) x1/2, y+3/2, z+2; (iii) x+3/2, y+2, z1/2; (iv) x+5/2, y+2, z+1/2.
 

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