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The mol­ecular conformation is stabilized by an intra­molecular O—H...O hydrogen bond between the hy­droxy substituent on the benzene ring and one of the carbonyl groups of the acridinedione unit.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S2056989021001341/hb7967sup1.cif
Contains datablocks global, I

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S2056989021001341/hb7967Isup2.hkl
Contains datablock I

cml

Chemical Markup Language (CML) file https://doi.org/10.1107/S2056989021001341/hb7967Isup3.cml
Supplementary material

CCDC reference: 2061379

Key indicators

  • Single-crystal X-ray study
  • T = 173 K
  • Mean [sigma](C-C) = 0.002 Å
  • Disorder in main residue
  • R factor = 0.045
  • wR factor = 0.126
  • Data-to-parameter ratio = 14.8

checkCIF/PLATON results

No syntax errors found



Alert level C PLAT410_ALERT_2_C Short Intra H...H Contact H12A ..H14A . 1.97 Ang. x,y,z = 1_555 Check PLAT480_ALERT_4_C Long H...A H-Bond Reported H14B ..O2 . 2.66 Ang. PLAT911_ALERT_3_C Missing FCF Refl Between Thmin & STh/L= 0.600 3 Report
Alert level G PLAT007_ALERT_5_G Number of Unrefined Donor-H Atoms .............. 1 Report PLAT171_ALERT_4_G The CIF-Embedded .res File Contains EADP Records 2 Report PLAT230_ALERT_2_G Hirshfeld Test Diff for O3A --C15 . 12.5 s.u. PLAT230_ALERT_2_G Hirshfeld Test Diff for C16 --C17A . 11.5 s.u. PLAT301_ALERT_3_G Main Residue Disorder ..............(Resd 1 ) 6% Note PLAT367_ALERT_2_G Long? C(sp?)-C(sp?) Bond C14 - C15 . 1.51 Ang. PLAT912_ALERT_4_G Missing # of FCF Reflections Above STh/L= 0.600 81 Note PLAT978_ALERT_2_G Number C-C Bonds with Positive Residual Density. 19 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 0 ALERT type 1 CIF construction/syntax error, inconsistent or missing data 5 ALERT type 2 Indicator that the structure model may be wrong or deficient 2 ALERT type 3 Indicator that the structure quality may be low 3 ALERT type 4 Improvement, methodology, query or suggestion 1 ALERT type 5 Informative message, check
checkCIF publication errors
Alert level A PUBL024_ALERT_1_A The number of authors is greater than 5. Please specify the role of each of the co-authors for your paper.
1 ALERT level A = Data missing that is essential or data in wrong format 0 ALERT level G = General alerts. Data that may be required is missing

Computing details top

Data collection: CrysAlis PRO (Rigaku OD, 2015); cell refinement: CrysAlis PRO (Rigaku OD, 2015); data reduction: CrysAlis PRO (Rigaku OD, 2015); program(s) used to solve structure: ShelXT (Sheldrick, 2015b); program(s) used to refine structure: SHELXL (Sheldrick, 2015a); molecular graphics: OLEX2 (Dolomanov et al., 2009); software used to prepare material for publication: OLEX2 (Dolomanov et al., 2009).

Ethyl 2-[9-(2-hydroxyphenyl)-3,3,6,6-tetramethyl-1,8-dioxo-2,3,4,4a,5,6,7,8a,9,9a,10,10a-dodecahydroacridin-10-yl]acetate top
Crystal data top
C27H33NO5F(000) = 968
Mr = 451.54Dx = 1.229 Mg m3
Monoclinic, P21/nCu Kα radiation, λ = 1.54184 Å
a = 9.5289 (2) ÅCell parameters from 3784 reflections
b = 18.6653 (5) Åθ = 4.0–71.4°
c = 13.8046 (3) ŵ = 0.68 mm1
β = 96.410 (2)°T = 173 K
V = 2439.93 (10) Å3Plate, yellow
Z = 40.48 × 0.22 × 0.08 mm
Data collection top
Rigaku Oxford Diffraction EOS
diffractometer
4648 independent reflections
Radiation source: fine-focus sealed X-ray tube, Enhance (Cu) X-ray Source3949 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.029
Detector resolution: 16.0416 pixels mm-1θmax = 71.2°, θmin = 4.0°
ω scansh = 1111
Absorption correction: multi-scan
(CrysalisPro; Rigaku OD, 2015)
k = 2214
Tmin = 0.861, Tmax = 1.000l = 1616
9527 measured reflections
Refinement top
Refinement on F2Primary atom site location: dual
Least-squares matrix: fullHydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.045H-atom parameters constrained
wR(F2) = 0.126 w = 1/[σ2(Fo2) + (0.0643P)2 + 0.6477P]
where P = (Fo2 + 2Fc2)/3
S = 1.04(Δ/σ)max < 0.001
4648 reflectionsΔρmax = 0.27 e Å3
313 parametersΔρmin = 0.23 e Å3
0 restraints
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*/UeqOcc. (<1)
O10.65518 (12)0.22713 (7)0.50403 (8)0.0373 (3)
O20.21715 (14)0.36821 (7)0.51857 (8)0.0426 (3)
O30.3445 (5)0.11473 (19)0.83632 (16)0.0636 (11)0.777 (9)
O3A0.2813 (17)0.1388 (6)0.8394 (7)0.0636 (11)0.223 (9)
O40.35606 (14)0.14006 (6)0.99586 (9)0.0406 (3)
O50.41985 (13)0.19489 (7)0.39430 (8)0.0389 (3)
H50.48870.21220.43000.058*
N10.44568 (13)0.24991 (6)0.79603 (8)0.0236 (2)
C10.54686 (14)0.22154 (7)0.74277 (10)0.0228 (3)
C20.66871 (16)0.18305 (8)0.79873 (11)0.0292 (3)
H2A0.63090.14640.84070.035*
H2B0.72340.21790.84190.035*
C30.76892 (16)0.14645 (9)0.73461 (12)0.0328 (3)
C40.79512 (16)0.19849 (9)0.65285 (12)0.0356 (4)
H4A0.84240.24210.68140.043*
H4B0.85870.17580.60980.043*
C50.65908 (16)0.21917 (8)0.59366 (11)0.0286 (3)
C60.53718 (15)0.23162 (8)0.64433 (10)0.0245 (3)
C70.40195 (15)0.25806 (8)0.58758 (10)0.0244 (3)
H70.42830.28800.53230.029*
C80.32755 (14)0.30588 (7)0.65354 (10)0.0237 (3)
C90.22950 (16)0.35939 (8)0.60657 (11)0.0291 (3)
C100.14223 (16)0.40152 (9)0.67124 (12)0.0323 (3)
H10A0.05810.37310.68330.039*
H10B0.10910.44630.63760.039*
C110.22671 (16)0.42010 (8)0.76873 (11)0.0280 (3)
C120.27846 (15)0.34965 (8)0.81805 (10)0.0263 (3)
H12A0.34610.36080.87580.032*
H12B0.19700.32450.84110.032*
C130.34886 (14)0.30040 (7)0.75185 (10)0.0222 (3)
C140.43949 (15)0.22835 (8)0.89738 (10)0.0256 (3)
H14A0.38580.26460.93040.031*
H14B0.53650.22650.93150.031*
C150.37019 (19)0.15605 (9)0.90423 (12)0.0368 (4)
C160.2856 (3)0.07304 (12)1.01388 (17)0.0641 (7)
H16A0.35530.03351.02180.077*0.725 (5)
H16B0.21460.06150.95810.077*0.725 (5)
H16C0.28720.04200.95590.077*0.275 (5)
H16D0.34050.04851.06930.077*0.275 (5)
C170.2157 (4)0.08124 (19)1.1040 (3)0.0665 (9)0.725 (5)
H17A0.28750.08801.15980.100*0.725 (5)
H17B0.16040.03811.11410.100*0.725 (5)
H17C0.15300.12301.09760.100*0.725 (5)
C17A0.1551 (11)0.0790 (5)1.0331 (8)0.0665 (9)0.275 (5)
H17D0.14990.11421.08530.100*0.275 (5)
H17E0.12170.03241.05410.100*0.275 (5)
H17F0.09560.09470.97450.100*0.275 (5)
C180.30828 (15)0.19663 (8)0.54418 (10)0.0258 (3)
C190.32270 (16)0.16932 (9)0.45105 (11)0.0307 (3)
C200.23375 (19)0.11504 (10)0.41156 (13)0.0405 (4)
H200.24280.09760.34790.049*
C210.13242 (18)0.08647 (9)0.46441 (14)0.0410 (4)
H210.07230.04930.43710.049*
C220.11833 (17)0.11164 (9)0.55659 (13)0.0356 (4)
H220.04940.09160.59330.043*
C230.20564 (16)0.16652 (8)0.59556 (11)0.0295 (3)
H230.19490.18390.65900.035*
C240.7045 (2)0.07682 (10)0.69143 (15)0.0469 (4)
H24A0.68940.04360.74430.070*
H24B0.76880.05500.64930.070*
H24C0.61390.08720.65310.070*
C250.9082 (2)0.12973 (11)0.79789 (14)0.0468 (4)
H25A0.95330.17460.82140.070*
H25B0.97130.10360.75900.070*
H25C0.88870.10030.85370.070*
C260.13320 (19)0.45952 (9)0.83469 (13)0.0405 (4)
H26A0.04950.43050.84240.061*
H26B0.10380.50570.80520.061*
H26C0.18640.46770.89870.061*
C270.35163 (17)0.46822 (8)0.75087 (12)0.0340 (3)
H27A0.40610.47990.81330.051*
H27B0.31630.51250.71870.051*
H27C0.41230.44310.70920.051*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
O10.0375 (6)0.0503 (7)0.0266 (6)0.0016 (5)0.0144 (4)0.0032 (5)
O20.0548 (7)0.0469 (7)0.0249 (6)0.0155 (6)0.0006 (5)0.0006 (5)
O30.114 (3)0.0437 (16)0.0360 (8)0.0364 (17)0.0192 (12)0.0122 (10)
O3A0.114 (3)0.0437 (16)0.0360 (8)0.0364 (17)0.0192 (12)0.0122 (10)
O40.0571 (7)0.0352 (6)0.0317 (6)0.0098 (5)0.0158 (5)0.0055 (5)
O50.0448 (6)0.0485 (7)0.0245 (5)0.0025 (5)0.0080 (5)0.0075 (5)
N10.0288 (6)0.0242 (6)0.0189 (5)0.0020 (5)0.0069 (4)0.0005 (4)
C10.0248 (6)0.0203 (6)0.0241 (7)0.0020 (5)0.0064 (5)0.0023 (5)
C20.0305 (7)0.0316 (7)0.0257 (7)0.0041 (6)0.0035 (6)0.0014 (6)
C30.0324 (8)0.0323 (8)0.0344 (8)0.0071 (6)0.0065 (6)0.0027 (6)
C40.0290 (8)0.0417 (9)0.0382 (9)0.0041 (6)0.0125 (6)0.0014 (7)
C50.0309 (7)0.0280 (7)0.0287 (7)0.0025 (6)0.0109 (6)0.0038 (6)
C60.0269 (7)0.0244 (7)0.0233 (7)0.0005 (5)0.0073 (5)0.0025 (5)
C70.0303 (7)0.0246 (7)0.0190 (6)0.0010 (6)0.0065 (5)0.0012 (5)
C80.0260 (6)0.0226 (7)0.0233 (7)0.0010 (5)0.0059 (5)0.0021 (5)
C90.0312 (7)0.0294 (7)0.0261 (7)0.0006 (6)0.0010 (6)0.0025 (6)
C100.0304 (7)0.0318 (8)0.0345 (8)0.0063 (6)0.0028 (6)0.0016 (6)
C110.0327 (7)0.0243 (7)0.0277 (7)0.0043 (6)0.0072 (6)0.0017 (6)
C120.0323 (7)0.0241 (7)0.0236 (7)0.0020 (6)0.0088 (5)0.0016 (5)
C130.0245 (6)0.0195 (6)0.0232 (7)0.0018 (5)0.0064 (5)0.0010 (5)
C140.0325 (7)0.0267 (7)0.0187 (6)0.0019 (6)0.0068 (5)0.0003 (5)
C150.0492 (9)0.0353 (8)0.0269 (8)0.0090 (7)0.0085 (6)0.0001 (6)
C160.0987 (18)0.0460 (12)0.0520 (12)0.0294 (12)0.0280 (12)0.0052 (9)
C170.082 (2)0.0543 (16)0.070 (2)0.0088 (15)0.0384 (17)0.0188 (17)
C17A0.082 (2)0.0543 (16)0.070 (2)0.0088 (15)0.0384 (17)0.0188 (17)
C180.0286 (7)0.0242 (7)0.0239 (7)0.0051 (5)0.0003 (5)0.0014 (5)
C190.0338 (8)0.0323 (8)0.0256 (7)0.0080 (6)0.0015 (6)0.0029 (6)
C200.0479 (9)0.0391 (9)0.0326 (8)0.0063 (7)0.0039 (7)0.0137 (7)
C210.0388 (9)0.0307 (8)0.0503 (10)0.0005 (7)0.0097 (7)0.0093 (7)
C220.0344 (8)0.0281 (8)0.0434 (9)0.0008 (6)0.0001 (7)0.0019 (7)
C230.0328 (7)0.0274 (7)0.0280 (7)0.0026 (6)0.0021 (6)0.0002 (6)
C240.0588 (11)0.0312 (9)0.0514 (11)0.0062 (8)0.0094 (8)0.0059 (8)
C250.0405 (10)0.0533 (11)0.0463 (10)0.0185 (8)0.0037 (8)0.0019 (8)
C260.0469 (10)0.0344 (8)0.0418 (9)0.0118 (7)0.0124 (7)0.0053 (7)
C270.0409 (8)0.0247 (7)0.0363 (8)0.0019 (6)0.0034 (6)0.0005 (6)
Geometric parameters (Å, º) top
O1—C51.2426 (19)C12—C131.5057 (18)
O2—C91.2185 (19)C14—H14A0.9900
O3—C151.217 (3)C14—H14B0.9900
O3A—C151.205 (11)C14—C151.510 (2)
O4—C151.321 (2)C16—H16A0.9900
O4—C161.454 (2)C16—H16B0.9900
O5—H50.8400C16—H16C0.9900
O5—C191.364 (2)C16—H16D0.9900
N1—C11.3816 (18)C16—C171.483 (4)
N1—C131.4091 (18)C16—C17A1.305 (9)
N1—C141.4633 (17)C17—H17A0.9800
C1—C21.504 (2)C17—H17B0.9800
C1—C61.365 (2)C17—H17C0.9800
C2—H2A0.9900C17A—H17D0.9800
C2—H2B0.9900C17A—H17E0.9800
C2—C31.533 (2)C17A—H17F0.9800
C3—C41.531 (2)C18—C191.404 (2)
C3—C241.530 (2)C18—C231.389 (2)
C3—C251.537 (2)C19—C201.392 (2)
C4—H4A0.9900C20—H200.9500
C4—H4B0.9900C20—C211.381 (3)
C4—C51.504 (2)C21—H210.9500
C5—C61.4401 (19)C21—C221.377 (3)
C6—C71.514 (2)C22—H220.9500
C7—H71.0000C22—C231.390 (2)
C7—C81.5074 (18)C23—H230.9500
C7—C181.5334 (19)C24—H24A0.9800
C8—C91.468 (2)C24—H24B0.9800
C8—C131.354 (2)C24—H24C0.9800
C9—C101.507 (2)C25—H25A0.9800
C10—H10A0.9900C25—H25B0.9800
C10—H10B0.9900C25—H25C0.9800
C10—C111.529 (2)C26—H26A0.9800
C11—C121.537 (2)C26—H26B0.9800
C11—C261.532 (2)C26—H26C0.9800
C11—C271.533 (2)C27—H27A0.9800
C12—H12A0.9900C27—H27B0.9800
C12—H12B0.9900C27—H27C0.9800
C15—O4—C16117.16 (15)O3—C15—O4124.13 (18)
C19—O5—H5109.5O3—C15—C14124.71 (17)
C1—N1—C13119.22 (11)O3A—C15—O4120.8 (5)
C1—N1—C14120.56 (12)O3A—C15—C14117.9 (5)
C13—N1—C14120.23 (11)O4—C15—C14110.73 (13)
N1—C1—C2117.03 (12)O4—C16—H16A110.0
C6—C1—N1120.23 (13)O4—C16—H16B110.0
C6—C1—C2122.68 (13)O4—C16—H16C108.4
C1—C2—H2A108.7O4—C16—H16D108.4
C1—C2—H2B108.7O4—C16—C17108.3 (2)
C1—C2—C3114.28 (12)H16A—C16—H16B108.4
H2A—C2—H2B107.6H16C—C16—H16D107.5
C3—C2—H2A108.7C17—C16—H16A110.0
C3—C2—H2B108.7C17—C16—H16B110.0
C2—C3—C25108.42 (13)C17A—C16—O4115.5 (4)
C4—C3—C2107.84 (13)C17A—C16—H16C108.4
C4—C3—C25110.27 (14)C17A—C16—H16D108.4
C24—C3—C2110.77 (14)C16—C17—H17A109.5
C24—C3—C4110.08 (14)C16—C17—H17B109.5
C24—C3—C25109.43 (15)C16—C17—H17C109.5
C3—C4—H4A109.4H17A—C17—H17B109.5
C3—C4—H4B109.4H17A—C17—H17C109.5
H4A—C4—H4B108.0H17B—C17—H17C109.5
C5—C4—C3111.22 (13)C16—C17A—H17D109.5
C5—C4—H4A109.4C16—C17A—H17E109.5
C5—C4—H4B109.4C16—C17A—H17F109.5
O1—C5—C4119.99 (13)H17D—C17A—H17E109.5
O1—C5—C6121.89 (14)H17D—C17A—H17F109.5
C6—C5—C4118.08 (13)H17E—C17A—H17F109.5
C1—C6—C5119.53 (13)C19—C18—C7121.14 (13)
C1—C6—C7121.28 (12)C23—C18—C7121.01 (13)
C5—C6—C7119.16 (12)C23—C18—C19117.85 (14)
C6—C7—H7107.8O5—C19—C18122.76 (14)
C6—C7—C18112.53 (11)O5—C19—C20116.89 (14)
C8—C7—C6108.12 (11)C20—C19—C18120.34 (15)
C8—C7—H7107.8C19—C20—H20119.8
C8—C7—C18112.73 (11)C21—C20—C19120.35 (15)
C18—C7—H7107.8C21—C20—H20119.8
C9—C8—C7117.07 (12)C20—C21—H21119.9
C13—C8—C7122.19 (13)C22—C21—C20120.17 (15)
C13—C8—C9120.73 (13)C22—C21—H21119.9
O2—C9—C8121.20 (14)C21—C22—H22120.2
O2—C9—C10121.44 (14)C21—C22—C23119.56 (16)
C8—C9—C10117.34 (13)C23—C22—H22120.2
C9—C10—H10A109.3C18—C23—C22121.71 (14)
C9—C10—H10B109.3C18—C23—H23119.1
C9—C10—C11111.62 (12)C22—C23—H23119.1
H10A—C10—H10B108.0C3—C24—H24A109.5
C11—C10—H10A109.3C3—C24—H24B109.5
C11—C10—H10B109.3C3—C24—H24C109.5
C10—C11—C12107.90 (12)H24A—C24—H24B109.5
C10—C11—C26110.38 (13)H24A—C24—H24C109.5
C10—C11—C27109.47 (13)H24B—C24—H24C109.5
C26—C11—C12109.08 (12)C3—C25—H25A109.5
C26—C11—C27109.14 (13)C3—C25—H25B109.5
C27—C11—C12110.87 (12)C3—C25—H25C109.5
C11—C12—H12A108.9H25A—C25—H25B109.5
C11—C12—H12B108.9H25A—C25—H25C109.5
H12A—C12—H12B107.7H25B—C25—H25C109.5
C13—C12—C11113.34 (12)C11—C26—H26A109.5
C13—C12—H12A108.9C11—C26—H26B109.5
C13—C12—H12B108.9C11—C26—H26C109.5
N1—C13—C12117.39 (12)H26A—C26—H26B109.5
C8—C13—N1120.15 (12)H26A—C26—H26C109.5
C8—C13—C12122.36 (13)H26B—C26—H26C109.5
N1—C14—H14A109.3C11—C27—H27A109.5
N1—C14—H14B109.3C11—C27—H27B109.5
N1—C14—C15111.74 (12)C11—C27—H27C109.5
H14A—C14—H14B107.9H27A—C27—H27B109.5
C15—C14—H14A109.3H27A—C27—H27C109.5
C15—C14—H14B109.3H27B—C27—H27C109.5
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
O5—H5···O10.841.812.6319 (17)166
C2—H2A···O2i0.992.523.1663 (19)123
C2—H2B···O5i0.992.533.457 (2)157
C12—H12B···O1ii0.992.523.2708 (17)133
C14—H14A···O1ii0.992.533.3299 (18)138
C14—H14B···O2i0.992.663.473 (2)140
C27—H27B···O3iii0.982.513.452 (3)161
Symmetry codes: (i) x+1/2, y+1/2, z+1/2; (ii) x1/2, y+1/2, z+1/2; (iii) x+1/2, y+1/2, z+3/2.
Short H···H interatomic contacts (Å) in the title compound top
ContactDistanceSymmetry operation
H21···H27A2.26-1/2 + x, 1/2 - y, -1/2 + z
H22···H27A2.461/2 - x, -1/2 + y, 3/2 - z
H22···H4B2.43-1 + x, y, z
 

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