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In the title compound, C20H19NO2, the phenanthrene moiety is non-planar, with the di­hydro­benzene ring distorted towards a twisted envelope conformation. The mol­ecules are linked into chains along the a axis by O—H...O hydrogen bonds; two other intermolecular hydrogen bonds interconnect these chains into a three-dimensional framework.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536803024590/cv6250sup1.cif
Contains datablocks global, I

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536803024590/cv6250Isup2.hkl
Contains datablock I

CCDC reference: 227872

Key indicators

  • Single-crystal X-ray study
  • T = 293 K
  • Mean [sigma](C-C) = 0.003 Å
  • R factor = 0.042
  • wR factor = 0.117
  • Data-to-parameter ratio = 12.1

checkCIF/PLATON results

No syntax errors found



Alert level B PLAT029_ALERT_3_B _diffrn_measured_fraction_theta_full Low ....... 0.98 PLAT222_ALERT_3_B Large Non-Solvent H Ueq(max)/Ueq(min) ... 5.00 Ratio
Alert level C PLAT066_ALERT_1_C Predicted and Reported Transmissions Identical . ? PLAT125_ALERT_4_C No _symmetry_space_group_name_Hall Given ....... ? PLAT220_ALERT_2_C Large Non-Solvent C Ueq(max)/Ueq(min) ... 2.88 Ratio
0 ALERT level A = In general: serious problem 2 ALERT level B = Potentially serious problem 3 ALERT level C = Check and explain 0 ALERT level G = General alerts; check 1 ALERT type 1 CIF construction/syntax error, inconsistent or missing data 1 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 1 ALERT type 4 Improvement, methodology, query or suggestion

Computing details top

Data collection: SMART (Siemens, 1996); cell refinement: SAINT (Siemens, 1996); data reduction: SAINT; program(s) used to solve structure: SHELXTL (Sheldrick, 1997); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL, PARST (Nardelli, 1995) and PLATON (Spek, 1990).

Ethyl 2-(acetylamino)-2-(9-hydroxy-10-oxo-9,10-dihydro-9-phenanthrenyl)acetate top
Crystal data top
C20H19NO5F(000) = 372
Mr = 353.36Dx = 1.360 Mg m3
Triclinic, P1Melting point: 162-164° K
a = 7.7205 (5) ÅMo Kα radiation, λ = 0.71073 Å
b = 8.8797 (6) ÅCell parameters from 3047 reflections
c = 14.1801 (10) Åθ = 2.6–28.3°
α = 82.795 (1)°µ = 0.10 mm1
β = 80.241 (1)°T = 293 K
γ = 64.415 (1)°Block, light yellow
V = 862.63 (10) Å30.48 × 0.22 × 0.18 mm
Z = 2
Data collection top
Siemens SMART CCD area-detector
diffractometer
2990 independent reflections
Radiation source: fine-focus sealed tube2553 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.011
Detector resolution: 8.33 pixels mm-1θmax = 25.0°, θmin = 2.6°
ω scansh = 59
Absorption correction: empirical (using intensity measurements)
(SADABS; Sheldrick, 1996)
k = 1010
Tmin = 0.954, Tmax = 0.983l = 1616
4335 measured reflections
Refinement top
Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.042Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.117H atoms treated by a mixture of independent and constrained refinement
S = 1.08 w = 1/[σ2(Fo2) + (0.0553P)2 + 0.2776P]
where P = (Fo2 + 2Fc2)/3
2990 reflections(Δ/σ)max < 0.001
248 parametersΔρmax = 0.29 e Å3
0 restraintsΔρmin = 0.19 e Å3
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
O10.68509 (19)0.03669 (17)0.13722 (9)0.0430 (3)
O20.6399 (2)0.10534 (18)0.31295 (10)0.0559 (4)
O31.10098 (19)0.23422 (17)0.08638 (9)0.0506 (4)
O41.05710 (18)0.27846 (15)0.24610 (9)0.0458 (3)
O51.2970 (2)0.0683 (2)0.17956 (10)0.0672 (5)
N11.0457 (2)0.09081 (19)0.11072 (10)0.0362 (3)
H2A0.995 (3)0.117 (2)0.0649 (15)0.046 (6)*
C10.6804 (2)0.2663 (2)0.21683 (12)0.0356 (4)
C20.6261 (3)0.3703 (2)0.13518 (13)0.0444 (4)
H20.62970.32470.07890.053*
C30.5665 (3)0.5410 (3)0.13691 (15)0.0538 (5)
H30.52850.60980.08220.065*
C40.5635 (3)0.6091 (3)0.21974 (17)0.0572 (5)
H40.52570.72360.22070.069*
C50.6167 (3)0.5071 (2)0.30100 (15)0.0509 (5)
H50.61370.55410.35660.061*
C60.6751 (2)0.3343 (2)0.30192 (12)0.0380 (4)
C70.7175 (2)0.2252 (2)0.39107 (12)0.0401 (4)
C80.7401 (3)0.2795 (3)0.47484 (14)0.0531 (5)
H80.73920.38480.47410.064*
C90.7638 (3)0.1786 (3)0.55865 (14)0.0610 (6)
H90.78040.21630.61330.073*
C100.7633 (3)0.0233 (3)0.56239 (14)0.0585 (6)
H100.77670.04250.61950.070*
C110.7427 (3)0.0338 (3)0.48122 (13)0.0510 (5)
H110.74200.13870.48330.061*
C120.7228 (2)0.0656 (2)0.39500 (12)0.0390 (4)
C130.6995 (2)0.0010 (2)0.30906 (12)0.0369 (4)
C140.7539 (2)0.0774 (2)0.21178 (11)0.0333 (4)
C150.9808 (2)0.0016 (2)0.18820 (11)0.0325 (4)
C161.0538 (2)0.1834 (2)0.16553 (12)0.0362 (4)
C171.0969 (3)0.4524 (3)0.23745 (17)0.0608 (6)
H17A1.21660.50630.19540.073*
H17B0.99280.45890.21080.073*
C181.1133 (5)0.5366 (4)0.3353 (2)0.0935 (9)
H18A1.12860.64930.33280.140*
H18B0.99820.47670.37750.140*
H18C1.22370.53800.35870.140*
C191.1999 (3)0.1214 (2)0.11252 (12)0.0402 (4)
C201.2471 (3)0.2251 (3)0.02954 (14)0.0538 (5)
H20A1.36720.22930.03500.081*
H20B1.14560.33640.02960.081*
H20C1.25870.17630.02920.081*
H151.034 (2)0.0015 (19)0.2411 (12)0.028 (4)*
H1A0.574 (4)0.041 (3)0.1590 (18)0.077 (8)*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
O10.0351 (7)0.0632 (8)0.0372 (7)0.0242 (6)0.0057 (5)0.0118 (6)
O20.0594 (9)0.0673 (9)0.0558 (9)0.0435 (8)0.0028 (7)0.0053 (7)
O30.0500 (8)0.0562 (8)0.0369 (7)0.0127 (6)0.0039 (6)0.0111 (6)
O40.0485 (7)0.0439 (7)0.0413 (7)0.0183 (6)0.0026 (6)0.0019 (5)
O50.0558 (9)0.1136 (13)0.0530 (9)0.0562 (9)0.0238 (7)0.0226 (8)
N10.0322 (7)0.0527 (9)0.0274 (8)0.0217 (7)0.0075 (6)0.0042 (6)
C10.0259 (8)0.0451 (10)0.0342 (9)0.0145 (7)0.0029 (6)0.0003 (7)
C20.0377 (10)0.0555 (12)0.0389 (10)0.0195 (9)0.0063 (7)0.0026 (8)
C30.0452 (11)0.0549 (12)0.0584 (13)0.0223 (9)0.0105 (9)0.0171 (10)
C40.0499 (12)0.0436 (11)0.0780 (15)0.0208 (9)0.0107 (10)0.0043 (10)
C50.0456 (11)0.0491 (11)0.0582 (12)0.0181 (9)0.0068 (9)0.0107 (9)
C60.0290 (8)0.0423 (10)0.0418 (9)0.0139 (7)0.0018 (7)0.0077 (7)
C70.0306 (9)0.0518 (11)0.0333 (9)0.0126 (8)0.0008 (7)0.0091 (8)
C80.0505 (11)0.0624 (13)0.0418 (11)0.0158 (10)0.0061 (9)0.0169 (9)
C90.0496 (12)0.0876 (17)0.0338 (10)0.0139 (11)0.0058 (8)0.0164 (10)
C100.0467 (11)0.0843 (16)0.0300 (10)0.0171 (11)0.0027 (8)0.0059 (10)
C110.0410 (10)0.0648 (13)0.0410 (10)0.0202 (9)0.0007 (8)0.0049 (9)
C120.0299 (8)0.0535 (11)0.0299 (9)0.0155 (8)0.0012 (6)0.0035 (7)
C130.0275 (8)0.0418 (9)0.0402 (9)0.0151 (7)0.0012 (7)0.0033 (7)
C140.0280 (8)0.0462 (10)0.0289 (8)0.0172 (7)0.0046 (6)0.0061 (7)
C150.0293 (8)0.0464 (10)0.0243 (8)0.0178 (7)0.0053 (6)0.0008 (7)
C160.0261 (8)0.0483 (10)0.0327 (9)0.0136 (7)0.0055 (6)0.0023 (7)
C170.0543 (12)0.0456 (11)0.0811 (16)0.0227 (10)0.0016 (11)0.0015 (10)
C180.107 (2)0.0690 (17)0.112 (2)0.0477 (17)0.0316 (18)0.0341 (16)
C190.0385 (9)0.0519 (11)0.0354 (9)0.0240 (8)0.0052 (7)0.0019 (8)
C200.0641 (13)0.0691 (13)0.0453 (11)0.0457 (11)0.0072 (9)0.0035 (9)
Geometric parameters (Å, º) top
O1—C141.4080 (19)C8—C91.384 (3)
O1—H1A0.85 (3)C8—H80.9300
O2—C131.209 (2)C9—C101.375 (3)
O3—C161.201 (2)C9—H90.9300
O4—C161.330 (2)C10—C111.373 (3)
O4—C171.456 (2)C10—H100.9300
O5—C191.230 (2)C11—C121.405 (3)
N1—C191.335 (2)C11—H110.9300
N1—C151.440 (2)C12—C131.478 (2)
N1—H2A0.77 (2)C13—C141.534 (2)
C1—C21.389 (2)C14—C151.572 (2)
C1—C61.402 (2)C15—C161.520 (2)
C1—C141.529 (2)C15—H150.916 (17)
C2—C31.383 (3)C17—C181.490 (4)
C2—H20.9300C17—H17A0.9700
C3—C41.379 (3)C17—H17B0.9700
C3—H30.9300C18—H18A0.9600
C4—C51.376 (3)C18—H18B0.9600
C4—H40.9300C18—H18C0.9600
C5—C61.399 (3)C19—C201.496 (2)
C5—H50.9300C20—H20A0.9600
C6—C71.484 (2)C20—H20B0.9600
C7—C121.395 (3)C20—H20C0.9600
C7—C81.400 (3)
C14—O1—H1A106.9 (17)C11—C12—C13118.90 (17)
C16—O4—C17117.47 (15)O2—C13—C12123.19 (16)
C19—N1—C15121.97 (14)O2—C13—C14120.32 (16)
C19—N1—H2A118.8 (15)C12—C13—C14116.49 (14)
C15—N1—H2A119.0 (15)O1—C14—C1112.05 (13)
C2—C1—C6120.02 (17)O1—C14—C13111.47 (13)
C2—C1—C14119.45 (15)C1—C14—C13109.74 (13)
C6—C1—C14120.48 (15)O1—C14—C15106.05 (13)
C3—C2—C1120.54 (18)C1—C14—C15108.84 (12)
C3—C2—H2119.7C13—C14—C15108.54 (13)
C1—C2—H2119.7N1—C15—C16110.91 (13)
C4—C3—C2120.02 (18)N1—C15—C14111.97 (13)
C4—C3—H3120.0C16—C15—C14109.64 (13)
C2—C3—H3120.0N1—C15—H15107.9 (10)
C5—C4—C3119.81 (19)C16—C15—H15106.7 (10)
C5—C4—H4120.1C14—C15—H15109.5 (10)
C3—C4—H4120.1O3—C16—O4124.74 (17)
C4—C5—C6121.54 (19)O3—C16—C15125.09 (15)
C4—C5—H5119.2O4—C16—C15110.18 (14)
C6—C5—H5119.2O4—C17—C18107.5 (2)
C5—C6—C1118.06 (17)O4—C17—H17A110.2
C5—C6—C7121.89 (16)C18—C17—H17A110.2
C1—C6—C7119.91 (15)O4—C17—H17B110.2
C12—C7—C8117.66 (17)C18—C17—H17B110.2
C12—C7—C6119.51 (15)H17A—C17—H17B108.5
C8—C7—C6122.69 (18)C17—C18—H18A109.5
C9—C8—C7120.8 (2)C17—C18—H18B109.5
C9—C8—H8119.6H18A—C18—H18B109.5
C7—C8—H8119.6C17—C18—H18C109.5
C10—C9—C8121.01 (19)H18A—C18—H18C109.5
C10—C9—H9119.5H18B—C18—H18C109.5
C8—C9—H9119.5O5—C19—N1121.59 (16)
C11—C10—C9119.50 (19)O5—C19—C20121.71 (16)
C11—C10—H10120.2N1—C19—C20116.69 (15)
C9—C10—H10120.2C19—C20—H20A109.5
C10—C11—C12120.2 (2)C19—C20—H20B109.5
C10—C11—H11119.9H20A—C20—H20B109.5
C12—C11—H11119.9C19—C20—H20C109.5
C7—C12—C11120.77 (17)H20A—C20—H20C109.5
C7—C12—C13120.28 (15)H20B—C20—H20C109.5
C6—C1—C2—C30.1 (3)C2—C1—C14—O124.4 (2)
C14—C1—C2—C3177.39 (15)C6—C1—C14—O1158.16 (14)
C1—C2—C3—C41.0 (3)C2—C1—C14—C13148.80 (15)
C2—C3—C4—C51.1 (3)C6—C1—C14—C1333.76 (19)
C3—C4—C5—C60.3 (3)C2—C1—C14—C1592.55 (17)
C4—C5—C6—C10.7 (3)C6—C1—C14—C1584.88 (17)
C4—C5—C6—C7175.00 (17)O2—C13—C14—O113.2 (2)
C2—C1—C6—C50.9 (2)C12—C13—C14—O1166.31 (14)
C14—C1—C6—C5176.52 (15)O2—C13—C14—C1137.96 (16)
C2—C1—C6—C7174.93 (15)C12—C13—C14—C141.58 (18)
C14—C1—C6—C77.6 (2)O2—C13—C14—C15103.22 (18)
C5—C6—C7—C12162.48 (16)C12—C13—C14—C1577.25 (17)
C1—C6—C7—C1213.2 (2)C19—N1—C15—C1698.40 (18)
C5—C6—C7—C813.1 (3)C19—N1—C15—C14138.77 (16)
C1—C6—C7—C8171.21 (16)O1—C14—C15—N174.20 (17)
C12—C7—C8—C91.0 (3)C1—C14—C15—N146.52 (17)
C6—C7—C8—C9174.70 (17)C13—C14—C15—N1165.92 (13)
C7—C8—C9—C100.9 (3)O1—C14—C15—C1649.35 (16)
C8—C9—C10—C111.3 (3)C1—C14—C15—C16170.07 (12)
C9—C10—C11—C120.1 (3)C13—C14—C15—C1670.53 (16)
C8—C7—C12—C112.4 (2)C17—O4—C16—O38.3 (2)
C6—C7—C12—C11173.42 (15)C17—O4—C16—C15171.44 (14)
C8—C7—C12—C13179.90 (16)N1—C15—C16—O323.2 (2)
C6—C7—C12—C134.1 (2)C14—C15—C16—O3100.97 (18)
C10—C11—C12—C72.0 (3)N1—C15—C16—O4157.11 (13)
C10—C11—C12—C13179.55 (16)C14—C15—C16—O478.72 (16)
C7—C12—C13—O2154.82 (18)C16—O4—C17—C18174.21 (18)
C11—C12—C13—O222.7 (3)C15—N1—C19—O51.9 (3)
C7—C12—C13—C1424.7 (2)C15—N1—C19—C20177.39 (16)
C11—C12—C13—C14157.76 (15)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
O1—H1A···O5i0.85 (3)2.02 (3)2.850 (2)167 (2)
N1—H2A···O3ii0.77 (2)2.36 (2)3.106 (2)164 (2)
C20—H20C···O1ii0.962.433.343 (3)159
Symmetry codes: (i) x1, y, z; (ii) x+2, y, z.
 

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