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The title compound, C21H13NO4, was prepared by the reaction of anthrone and 4-hydr­oxy-3-nitro­benzaldehyde catalysed by anhydrous hydrogen chloride. In the mol­ecule, the anthraquinone fragment is non-planar; the central six-membered ring adopts an asymmetric boat conformation, while the two outer rings make a dihedral angle of 36.0 (1)°. Weak inter­molecular C—H...O hydrogen bonds link the mol­ecules into centrosymmetric dimers.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536806049051/cv2149sup1.cif
Contains datablocks global, I

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536806049051/cv2149Isup2.hkl
Contains datablock I

CCDC reference: 295085

Key indicators

  • Single-crystal X-ray study
  • T = 293 K
  • Mean [sigma](C-C) = 0.004 Å
  • R factor = 0.045
  • wR factor = 0.137
  • Data-to-parameter ratio = 11.6

checkCIF/PLATON results

No syntax errors found



Alert level C PLAT066_ALERT_1_C Predicted and Reported Transmissions Identical . ? PLAT152_ALERT_1_C Supplied and Calc Volume s.u. Inconsistent ..... ? PLAT790_ALERT_4_C Centre of Gravity not Within Unit Cell: Resd. # 1 C21 H13 N O4
Alert level G PLAT199_ALERT_1_G Check the Reported _cell_measurement_temperature 293 K PLAT200_ALERT_1_G Check the Reported _diffrn_ambient_temperature . 293 K
0 ALERT level A = In general: serious problem 0 ALERT level B = Potentially serious problem 3 ALERT level C = Check and explain 2 ALERT level G = General alerts; check 4 ALERT type 1 CIF construction/syntax error, inconsistent or missing data 0 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

Computing details top

Data collection: CAD-4 EXPRESS (Enraf–Nonius, 1994); cell refinement: CAD-4 EXPRESS; data reduction: XCAD4 (Harms & Wocadlo, 1995); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEP-3 for Windows (Version 1.05; Farrugia, 1997); software used to prepare material for publication: SHELXL97.

10-(4-Hydroxy-3-nitrobenzylidene)anthrone top
Crystal data top
C21H13NO4F(000) = 712
Mr = 343.32Dx = 1.465 Mg m3
Monoclinic, P21/cMo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybcCell parameters from 25 reflections
a = 8.545 (4) Åθ = 10.3–13.2°
b = 14.588 (3) ŵ = 0.10 mm1
c = 13.916 (4) ÅT = 293 K
β = 116.22 (2)°Prism, orange
V = 1556.3 (9) Å30.50 × 0.30 × 0.20 mm
Z = 4
Data collection top
Enraf–Nonius CAD-4
diffractometer
1590 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tubeRint = 0.041
Graphite monochromatorθmax = 25.2°, θmin = 2.2°
ω/2θ scansh = 100
Absorption correction: ψ scan
(North et al., 1968)
k = 171
Tmin = 0.951, Tmax = 0.980l = 1416
3238 measured reflections3 standard reflections every 60 min
2790 independent reflections intensity decay: none
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)] = 0.045H atoms treated by a mixture of independent and constrained refinement
wR(F2) = 0.137 w = 1/[σ2(Fo2) + (0.067P)2 + 0.1995P]
where P = (Fo2 + 2Fc2)/3
S = 1.04(Δ/σ)max < 0.001
2790 reflectionsΔρmax = 0.18 e Å3
240 parametersΔρmin = 0.20 e Å3
1 restraintExtinction correction: SHELXL97, Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
Primary atom site location: structure-invariant direct methodsExtinction coefficient: 0.011 (2)
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
xyzUiso*/Ueq
O10.3582 (3)0.10060 (16)0.86240 (18)0.0678 (7)
O20.5665 (3)0.34005 (18)0.68504 (19)0.0673 (7)
H2X0.631 (5)0.387 (2)0.712 (3)0.106 (16)*
O30.7141 (3)0.47767 (16)0.80674 (17)0.0623 (6)
O40.6001 (3)0.54189 (15)0.90031 (17)0.0596 (6)
N10.6017 (3)0.48083 (17)0.84083 (18)0.0443 (6)
C10.0493 (4)0.0191 (2)0.8694 (2)0.0484 (7)
H10.14250.02030.85530.058*
C20.1038 (4)0.0151 (2)0.8740 (2)0.0542 (8)
H20.11360.07710.86190.065*
C30.2424 (4)0.0431 (2)0.8968 (2)0.0535 (8)
H30.34780.01990.90300.064*
C40.2264 (4)0.13539 (19)0.9103 (2)0.0462 (7)
H40.32090.17390.92460.055*
C50.0494 (3)0.27059 (18)0.9181 (2)0.0351 (6)
C60.0391 (4)0.36772 (18)1.0363 (2)0.0416 (7)
H60.04660.41021.04360.050*
C70.1398 (4)0.3813 (2)1.0896 (2)0.0476 (7)
H70.11900.43191.13430.057*
C80.2714 (4)0.3206 (2)1.0775 (2)0.0530 (8)
H80.33960.33061.11320.064*
C90.3007 (4)0.2456 (2)1.0124 (2)0.0482 (8)
H90.39000.20501.00350.058*
C100.2234 (4)0.1449 (2)0.8964 (2)0.0442 (7)
C110.0711 (3)0.17231 (18)0.9030 (2)0.0376 (6)
C120.0640 (3)0.29100 (17)0.9713 (2)0.0365 (6)
C130.1975 (3)0.22966 (18)0.9594 (2)0.0388 (7)
C140.0665 (4)0.11161 (18)0.8856 (2)0.0398 (7)
C150.1234 (3)0.34030 (19)0.8892 (2)0.0401 (7)
H150.10090.39810.90840.048*
C160.2342 (3)0.34060 (18)0.8322 (2)0.0375 (6)
C170.2152 (4)0.2792 (2)0.7506 (2)0.0476 (7)
H170.12560.23630.72830.057*
C180.3253 (4)0.2805 (2)0.7026 (2)0.0519 (8)
H180.31010.23810.64920.062*
C190.4594 (4)0.3447 (2)0.7331 (2)0.0447 (7)
C200.4721 (3)0.40921 (18)0.80923 (19)0.0354 (6)
C210.3607 (3)0.40713 (18)0.85801 (19)0.0362 (6)
H210.37190.45130.90880.043*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
O10.0418 (12)0.0759 (15)0.0851 (16)0.0251 (11)0.0276 (12)0.0126 (13)
O20.0693 (15)0.0870 (18)0.0730 (15)0.0106 (14)0.0566 (13)0.0209 (14)
O30.0473 (12)0.0884 (17)0.0681 (14)0.0147 (12)0.0409 (11)0.0039 (12)
O40.0646 (14)0.0635 (14)0.0655 (14)0.0240 (12)0.0422 (12)0.0188 (12)
N10.0381 (13)0.0585 (16)0.0441 (13)0.0064 (12)0.0252 (11)0.0030 (12)
C10.0583 (19)0.0443 (17)0.0445 (16)0.0125 (15)0.0244 (15)0.0040 (14)
C20.076 (2)0.0401 (16)0.0526 (18)0.0035 (17)0.0339 (17)0.0031 (14)
C30.0528 (19)0.057 (2)0.0564 (18)0.0146 (16)0.0289 (16)0.0024 (16)
C40.0396 (16)0.0501 (18)0.0528 (18)0.0013 (13)0.0241 (14)0.0002 (14)
C50.0282 (13)0.0405 (15)0.0390 (14)0.0043 (11)0.0169 (12)0.0010 (12)
C60.0406 (15)0.0411 (16)0.0495 (16)0.0012 (12)0.0256 (13)0.0048 (13)
C70.0548 (18)0.0465 (17)0.0524 (17)0.0115 (14)0.0335 (15)0.0064 (14)
C80.0484 (17)0.062 (2)0.0641 (19)0.0187 (16)0.0391 (16)0.0141 (17)
C90.0304 (15)0.062 (2)0.0598 (18)0.0045 (14)0.0265 (14)0.0141 (16)
C100.0324 (14)0.0555 (18)0.0454 (15)0.0062 (14)0.0179 (12)0.0065 (14)
C110.0368 (14)0.0428 (16)0.0375 (14)0.0046 (13)0.0204 (12)0.0004 (12)
C120.0325 (14)0.0400 (15)0.0409 (15)0.0026 (12)0.0197 (12)0.0078 (13)
C130.0310 (14)0.0454 (17)0.0433 (15)0.0007 (12)0.0194 (12)0.0075 (13)
C140.0419 (15)0.0426 (17)0.0361 (14)0.0040 (13)0.0182 (12)0.0015 (12)
C150.0387 (15)0.0422 (16)0.0468 (16)0.0055 (13)0.0257 (13)0.0045 (13)
C160.0356 (14)0.0409 (15)0.0409 (14)0.0042 (12)0.0214 (12)0.0016 (12)
C170.0525 (18)0.0501 (18)0.0468 (16)0.0170 (14)0.0279 (15)0.0093 (14)
C180.0589 (19)0.0594 (19)0.0445 (17)0.0114 (16)0.0292 (15)0.0132 (15)
C190.0437 (16)0.0580 (19)0.0427 (16)0.0027 (15)0.0285 (14)0.0006 (14)
C200.0325 (14)0.0413 (15)0.0367 (14)0.0034 (12)0.0192 (12)0.0013 (12)
C210.0375 (14)0.0405 (15)0.0358 (13)0.0008 (12)0.0209 (12)0.0009 (12)
Geometric parameters (Å, º) top
O1—C101.219 (3)C7—C81.382 (4)
O2—C191.352 (3)C7—H70.9300
O2—H2X0.86 (4)C8—C91.371 (4)
O3—N11.246 (3)C8—H80.9300
O4—N11.220 (3)C9—C131.396 (4)
N1—C201.443 (3)C9—H90.9300
C1—C21.375 (4)C10—C131.475 (4)
C1—C141.387 (4)C10—C141.495 (4)
C1—H10.9300C11—C141.405 (4)
C2—C31.376 (4)C12—C131.401 (3)
C2—H20.9300C15—C161.480 (3)
C3—C41.374 (4)C15—H150.9300
C3—H30.9300C16—C211.377 (4)
C4—C111.393 (4)C16—C171.398 (4)
C4—H40.9300C17—C181.374 (4)
C5—C151.349 (3)C17—H170.9300
C5—C111.473 (4)C18—C191.394 (4)
C5—C121.487 (3)C18—H180.9300
C6—C71.377 (4)C19—C201.385 (4)
C6—C121.394 (4)C20—C211.392 (3)
C6—H60.9300C21—H210.9300
C19—O2—H2X101 (3)C4—C11—C14117.8 (2)
O4—N1—O3121.8 (2)C4—C11—C5122.8 (2)
O4—N1—C20119.9 (2)C14—C11—C5119.3 (2)
O3—N1—C20118.3 (2)C6—C12—C13118.2 (2)
C2—C1—C14120.9 (3)C6—C12—C5122.5 (2)
C2—C1—H1119.6C13—C12—C5119.3 (2)
C14—C1—H1119.6C9—C13—C12120.1 (3)
C1—C2—C3119.4 (3)C9—C13—C10119.3 (2)
C1—C2—H2120.3C12—C13—C10120.4 (2)
C3—C2—H2120.3C1—C14—C11120.0 (3)
C4—C3—C2120.6 (3)C1—C14—C10119.8 (2)
C4—C3—H3119.7C11—C14—C10119.8 (2)
C2—C3—H3119.7C5—C15—C16131.1 (3)
C3—C4—C11121.2 (3)C5—C15—H15114.5
C3—C4—H4119.4C16—C15—H15114.5
C11—C4—H4119.4C21—C16—C17117.4 (2)
C15—C5—C11125.9 (2)C21—C16—C15118.5 (2)
C15—C5—C12119.5 (2)C17—C16—C15124.1 (2)
C11—C5—C12114.7 (2)C18—C17—C16121.8 (3)
C7—C6—C12120.8 (3)C18—C17—H17119.1
C7—C6—H6119.6C16—C17—H17119.1
C12—C6—H6119.6C17—C18—C19120.6 (3)
C6—C7—C8120.7 (3)C17—C18—H18119.7
C6—C7—H7119.7C19—C18—H18119.7
C8—C7—H7119.7O2—C19—C20124.9 (3)
C9—C8—C7119.6 (3)O2—C19—C18117.4 (3)
C9—C8—H8120.2C20—C19—C18117.7 (2)
C7—C8—H8120.2C19—C20—C21121.3 (2)
C8—C9—C13120.5 (3)C19—C20—N1121.0 (2)
C8—C9—H9119.7C21—C20—N1117.7 (2)
C13—C9—H9119.7C16—C21—C20121.0 (2)
O1—C10—C13122.9 (3)C16—C21—H21119.5
O1—C10—C14121.6 (3)C20—C21—H21119.5
C13—C10—C14115.3 (2)
C14—C1—C2—C31.1 (4)C4—C11—C14—C14.1 (4)
C1—C2—C3—C42.8 (4)C5—C11—C14—C1178.9 (2)
C2—C3—C4—C110.9 (5)C4—C11—C14—C10169.2 (2)
C12—C6—C7—C81.9 (4)C5—C11—C14—C107.8 (4)
C6—C7—C8—C90.6 (4)O1—C10—C14—C121.1 (4)
C7—C8—C9—C130.7 (4)C13—C10—C14—C1153.3 (3)
C3—C4—C11—C142.5 (4)O1—C10—C14—C11165.6 (3)
C3—C4—C11—C5179.3 (3)C13—C10—C14—C1120.0 (3)
C15—C5—C11—C434.6 (4)C11—C5—C15—C163.4 (5)
C12—C5—C11—C4144.8 (3)C12—C5—C15—C16177.2 (3)
C15—C5—C11—C14148.7 (3)C5—C15—C16—C21147.3 (3)
C12—C5—C11—C1432.0 (3)C5—C15—C16—C1735.0 (5)
C7—C6—C12—C131.8 (4)C21—C16—C17—C184.4 (4)
C7—C6—C12—C5175.9 (3)C15—C16—C17—C18177.9 (3)
C15—C5—C12—C630.4 (4)C16—C17—C18—C190.9 (5)
C11—C5—C12—C6149.0 (2)C17—C18—C19—O2177.8 (3)
C15—C5—C12—C13151.9 (2)C17—C18—C19—C203.0 (4)
C11—C5—C12—C1328.7 (3)O2—C19—C20—C21177.4 (3)
C8—C9—C13—C120.8 (4)C18—C19—C20—C213.4 (4)
C8—C9—C13—C10175.5 (3)O2—C19—C20—N12.4 (4)
C6—C12—C13—C90.5 (4)C18—C19—C20—N1176.8 (3)
C5—C12—C13—C9177.3 (2)O4—N1—C20—C19173.1 (2)
C6—C12—C13—C10176.7 (2)O3—N1—C20—C197.6 (4)
C5—C12—C13—C101.1 (4)O4—N1—C20—C217.0 (4)
O1—C10—C13—C921.5 (4)O3—N1—C20—C21172.3 (2)
C14—C10—C13—C9152.9 (2)C17—C16—C21—C203.9 (4)
O1—C10—C13—C12162.3 (3)C15—C16—C21—C20178.1 (2)
C14—C10—C13—C1223.3 (3)C19—C20—C21—C160.1 (4)
C2—C1—C14—C112.4 (4)N1—C20—C21—C16179.8 (2)
C2—C1—C14—C10170.9 (2)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
O2—H2X···O30.86 (4)1.78 (3)2.569 (3)153 (4)
C21—H21···O4i0.932.563.314 (3)138
Symmetry code: (i) x+1, y1, z+2.
 

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