In the title compound, C
20H
19NO
2, 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
CCDC reference: 227872
Key indicators
- Single-crystal X-ray study
- T = 293 K
- Mean (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
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
C20H19NO5 | F(000) = 372 |
Mr = 353.36 | Dx = 1.360 Mg m−3 |
Triclinic, P1 | Melting point: 162-164° K |
a = 7.7205 (5) Å | Mo Kα radiation, λ = 0.71073 Å |
b = 8.8797 (6) Å | Cell parameters from 3047 reflections |
c = 14.1801 (10) Å | θ = 2.6–28.3° |
α = 82.795 (1)° | µ = 0.10 mm−1 |
β = 80.241 (1)° | T = 293 K |
γ = 64.415 (1)° | Block, light yellow |
V = 862.63 (10) Å3 | 0.48 × 0.22 × 0.18 mm |
Z = 2 | |
Data collection top
Siemens SMART CCD area-detector diffractometer | 2990 independent reflections |
Radiation source: fine-focus sealed tube | 2553 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.011 |
Detector resolution: 8.33 pixels mm-1 | θmax = 25.0°, θmin = 2.6° |
ω scans | h = −5→9 |
Absorption correction: empirical (using intensity measurements) (SADABS; Sheldrick, 1996) | k = −10→10 |
Tmin = 0.954, Tmax = 0.983 | l = −16→16 |
4335 measured reflections | |
Refinement top
Refinement on F2 | Primary atom site location: structure-invariant direct methods |
Least-squares matrix: full | Secondary atom site location: difference Fourier map |
R[F2 > 2σ(F2)] = 0.042 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.117 | H 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 parameters | Δρmax = 0.29 e Å−3 |
0 restraints | Δρmin = −0.19 e Å−3 |
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 | x | y | z | Uiso*/Ueq | |
O1 | 0.68509 (19) | 0.03669 (17) | 0.13722 (9) | 0.0430 (3) | |
O2 | 0.6399 (2) | −0.10534 (18) | 0.31295 (10) | 0.0559 (4) | |
O3 | 1.10098 (19) | −0.23422 (17) | 0.08638 (9) | 0.0506 (4) | |
O4 | 1.05710 (18) | −0.27846 (15) | 0.24610 (9) | 0.0458 (3) | |
O5 | 1.2970 (2) | 0.0683 (2) | 0.17956 (10) | 0.0672 (5) | |
N1 | 1.0457 (2) | 0.09081 (19) | 0.11072 (10) | 0.0362 (3) | |
H2A | 0.995 (3) | 0.117 (2) | 0.0649 (15) | 0.046 (6)* | |
C1 | 0.6804 (2) | 0.2663 (2) | 0.21683 (12) | 0.0356 (4) | |
C2 | 0.6261 (3) | 0.3703 (2) | 0.13518 (13) | 0.0444 (4) | |
H2 | 0.6297 | 0.3247 | 0.0789 | 0.053* | |
C3 | 0.5665 (3) | 0.5410 (3) | 0.13691 (15) | 0.0538 (5) | |
H3 | 0.5285 | 0.6098 | 0.0822 | 0.065* | |
C4 | 0.5635 (3) | 0.6091 (3) | 0.21974 (17) | 0.0572 (5) | |
H4 | 0.5257 | 0.7236 | 0.2207 | 0.069* | |
C5 | 0.6167 (3) | 0.5071 (2) | 0.30100 (15) | 0.0509 (5) | |
H5 | 0.6137 | 0.5541 | 0.3566 | 0.061* | |
C6 | 0.6751 (2) | 0.3343 (2) | 0.30192 (12) | 0.0380 (4) | |
C7 | 0.7175 (2) | 0.2252 (2) | 0.39107 (12) | 0.0401 (4) | |
C8 | 0.7401 (3) | 0.2795 (3) | 0.47484 (14) | 0.0531 (5) | |
H8 | 0.7392 | 0.3848 | 0.4741 | 0.064* | |
C9 | 0.7638 (3) | 0.1786 (3) | 0.55865 (14) | 0.0610 (6) | |
H9 | 0.7804 | 0.2163 | 0.6133 | 0.073* | |
C10 | 0.7633 (3) | 0.0233 (3) | 0.56239 (14) | 0.0585 (6) | |
H10 | 0.7767 | −0.0425 | 0.6195 | 0.070* | |
C11 | 0.7427 (3) | −0.0338 (3) | 0.48122 (13) | 0.0510 (5) | |
H11 | 0.7420 | −0.1387 | 0.4833 | 0.061* | |
C12 | 0.7228 (2) | 0.0656 (2) | 0.39500 (12) | 0.0390 (4) | |
C13 | 0.6995 (2) | 0.0010 (2) | 0.30906 (12) | 0.0369 (4) | |
C14 | 0.7539 (2) | 0.0774 (2) | 0.21178 (11) | 0.0333 (4) | |
C15 | 0.9808 (2) | −0.0016 (2) | 0.18820 (11) | 0.0325 (4) | |
C16 | 1.0538 (2) | −0.1834 (2) | 0.16553 (12) | 0.0362 (4) | |
C17 | 1.0969 (3) | −0.4524 (3) | 0.23745 (17) | 0.0608 (6) | |
H17A | 1.2166 | −0.5063 | 0.1954 | 0.073* | |
H17B | 0.9928 | −0.4589 | 0.2108 | 0.073* | |
C18 | 1.1133 (5) | −0.5366 (4) | 0.3353 (2) | 0.0935 (9) | |
H18A | 1.1286 | −0.6493 | 0.3328 | 0.140* | |
H18B | 0.9982 | −0.4767 | 0.3775 | 0.140* | |
H18C | 1.2237 | −0.5380 | 0.3587 | 0.140* | |
C19 | 1.1999 (3) | 0.1214 (2) | 0.11252 (12) | 0.0402 (4) | |
C20 | 1.2471 (3) | 0.2251 (3) | 0.02954 (14) | 0.0538 (5) | |
H20A | 1.3672 | 0.2293 | 0.0350 | 0.081* | |
H20B | 1.1456 | 0.3364 | 0.0296 | 0.081* | |
H20C | 1.2587 | 0.1763 | −0.0292 | 0.081* | |
H15 | 1.034 (2) | −0.0015 (19) | 0.2411 (12) | 0.028 (4)* | |
H1A | 0.574 (4) | 0.041 (3) | 0.1590 (18) | 0.077 (8)* | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
O1 | 0.0351 (7) | 0.0632 (8) | 0.0372 (7) | −0.0242 (6) | −0.0057 (5) | −0.0118 (6) |
O2 | 0.0594 (9) | 0.0673 (9) | 0.0558 (9) | −0.0435 (8) | 0.0028 (7) | −0.0053 (7) |
O3 | 0.0500 (8) | 0.0562 (8) | 0.0369 (7) | −0.0127 (6) | −0.0039 (6) | −0.0111 (6) |
O4 | 0.0485 (7) | 0.0439 (7) | 0.0413 (7) | −0.0183 (6) | −0.0026 (6) | 0.0019 (5) |
O5 | 0.0558 (9) | 0.1136 (13) | 0.0530 (9) | −0.0562 (9) | −0.0238 (7) | 0.0226 (8) |
N1 | 0.0322 (7) | 0.0527 (9) | 0.0274 (8) | −0.0217 (7) | −0.0075 (6) | 0.0042 (6) |
C1 | 0.0259 (8) | 0.0451 (10) | 0.0342 (9) | −0.0145 (7) | −0.0029 (6) | 0.0003 (7) |
C2 | 0.0377 (10) | 0.0555 (12) | 0.0389 (10) | −0.0195 (9) | −0.0063 (7) | 0.0026 (8) |
C3 | 0.0452 (11) | 0.0549 (12) | 0.0584 (13) | −0.0223 (9) | −0.0105 (9) | 0.0171 (10) |
C4 | 0.0499 (12) | 0.0436 (11) | 0.0780 (15) | −0.0208 (9) | −0.0107 (10) | 0.0043 (10) |
C5 | 0.0456 (11) | 0.0491 (11) | 0.0582 (12) | −0.0181 (9) | −0.0068 (9) | −0.0107 (9) |
C6 | 0.0290 (8) | 0.0423 (10) | 0.0418 (9) | −0.0139 (7) | −0.0018 (7) | −0.0077 (7) |
C7 | 0.0306 (9) | 0.0518 (11) | 0.0333 (9) | −0.0126 (8) | −0.0008 (7) | −0.0091 (8) |
C8 | 0.0505 (11) | 0.0624 (13) | 0.0418 (11) | −0.0158 (10) | −0.0061 (9) | −0.0169 (9) |
C9 | 0.0496 (12) | 0.0876 (17) | 0.0338 (10) | −0.0139 (11) | −0.0058 (8) | −0.0164 (10) |
C10 | 0.0467 (11) | 0.0843 (16) | 0.0300 (10) | −0.0171 (11) | −0.0027 (8) | 0.0059 (10) |
C11 | 0.0410 (10) | 0.0648 (13) | 0.0410 (10) | −0.0202 (9) | −0.0007 (8) | 0.0049 (9) |
C12 | 0.0299 (8) | 0.0535 (11) | 0.0299 (9) | −0.0155 (8) | 0.0012 (6) | −0.0035 (7) |
C13 | 0.0275 (8) | 0.0418 (9) | 0.0402 (9) | −0.0151 (7) | 0.0012 (7) | −0.0033 (7) |
C14 | 0.0280 (8) | 0.0462 (10) | 0.0289 (8) | −0.0172 (7) | −0.0046 (6) | −0.0061 (7) |
C15 | 0.0293 (8) | 0.0464 (10) | 0.0243 (8) | −0.0178 (7) | −0.0053 (6) | −0.0008 (7) |
C16 | 0.0261 (8) | 0.0483 (10) | 0.0327 (9) | −0.0136 (7) | −0.0055 (6) | −0.0023 (7) |
C17 | 0.0543 (12) | 0.0456 (11) | 0.0811 (16) | −0.0227 (10) | −0.0016 (11) | −0.0015 (10) |
C18 | 0.107 (2) | 0.0690 (17) | 0.112 (2) | −0.0477 (17) | −0.0316 (18) | 0.0341 (16) |
C19 | 0.0385 (9) | 0.0519 (11) | 0.0354 (9) | −0.0240 (8) | −0.0052 (7) | −0.0019 (8) |
C20 | 0.0641 (13) | 0.0691 (13) | 0.0453 (11) | −0.0457 (11) | −0.0072 (9) | 0.0035 (9) |
Geometric parameters (Å, º) top
O1—C14 | 1.4080 (19) | C8—C9 | 1.384 (3) |
O1—H1A | 0.85 (3) | C8—H8 | 0.9300 |
O2—C13 | 1.209 (2) | C9—C10 | 1.375 (3) |
O3—C16 | 1.201 (2) | C9—H9 | 0.9300 |
O4—C16 | 1.330 (2) | C10—C11 | 1.373 (3) |
O4—C17 | 1.456 (2) | C10—H10 | 0.9300 |
O5—C19 | 1.230 (2) | C11—C12 | 1.405 (3) |
N1—C19 | 1.335 (2) | C11—H11 | 0.9300 |
N1—C15 | 1.440 (2) | C12—C13 | 1.478 (2) |
N1—H2A | 0.77 (2) | C13—C14 | 1.534 (2) |
C1—C2 | 1.389 (2) | C14—C15 | 1.572 (2) |
C1—C6 | 1.402 (2) | C15—C16 | 1.520 (2) |
C1—C14 | 1.529 (2) | C15—H15 | 0.916 (17) |
C2—C3 | 1.383 (3) | C17—C18 | 1.490 (4) |
C2—H2 | 0.9300 | C17—H17A | 0.9700 |
C3—C4 | 1.379 (3) | C17—H17B | 0.9700 |
C3—H3 | 0.9300 | C18—H18A | 0.9600 |
C4—C5 | 1.376 (3) | C18—H18B | 0.9600 |
C4—H4 | 0.9300 | C18—H18C | 0.9600 |
C5—C6 | 1.399 (3) | C19—C20 | 1.496 (2) |
C5—H5 | 0.9300 | C20—H20A | 0.9600 |
C6—C7 | 1.484 (2) | C20—H20B | 0.9600 |
C7—C12 | 1.395 (3) | C20—H20C | 0.9600 |
C7—C8 | 1.400 (3) | | |
| | | |
C14—O1—H1A | 106.9 (17) | C11—C12—C13 | 118.90 (17) |
C16—O4—C17 | 117.47 (15) | O2—C13—C12 | 123.19 (16) |
C19—N1—C15 | 121.97 (14) | O2—C13—C14 | 120.32 (16) |
C19—N1—H2A | 118.8 (15) | C12—C13—C14 | 116.49 (14) |
C15—N1—H2A | 119.0 (15) | O1—C14—C1 | 112.05 (13) |
C2—C1—C6 | 120.02 (17) | O1—C14—C13 | 111.47 (13) |
C2—C1—C14 | 119.45 (15) | C1—C14—C13 | 109.74 (13) |
C6—C1—C14 | 120.48 (15) | O1—C14—C15 | 106.05 (13) |
C3—C2—C1 | 120.54 (18) | C1—C14—C15 | 108.84 (12) |
C3—C2—H2 | 119.7 | C13—C14—C15 | 108.54 (13) |
C1—C2—H2 | 119.7 | N1—C15—C16 | 110.91 (13) |
C4—C3—C2 | 120.02 (18) | N1—C15—C14 | 111.97 (13) |
C4—C3—H3 | 120.0 | C16—C15—C14 | 109.64 (13) |
C2—C3—H3 | 120.0 | N1—C15—H15 | 107.9 (10) |
C5—C4—C3 | 119.81 (19) | C16—C15—H15 | 106.7 (10) |
C5—C4—H4 | 120.1 | C14—C15—H15 | 109.5 (10) |
C3—C4—H4 | 120.1 | O3—C16—O4 | 124.74 (17) |
C4—C5—C6 | 121.54 (19) | O3—C16—C15 | 125.09 (15) |
C4—C5—H5 | 119.2 | O4—C16—C15 | 110.18 (14) |
C6—C5—H5 | 119.2 | O4—C17—C18 | 107.5 (2) |
C5—C6—C1 | 118.06 (17) | O4—C17—H17A | 110.2 |
C5—C6—C7 | 121.89 (16) | C18—C17—H17A | 110.2 |
C1—C6—C7 | 119.91 (15) | O4—C17—H17B | 110.2 |
C12—C7—C8 | 117.66 (17) | C18—C17—H17B | 110.2 |
C12—C7—C6 | 119.51 (15) | H17A—C17—H17B | 108.5 |
C8—C7—C6 | 122.69 (18) | C17—C18—H18A | 109.5 |
C9—C8—C7 | 120.8 (2) | C17—C18—H18B | 109.5 |
C9—C8—H8 | 119.6 | H18A—C18—H18B | 109.5 |
C7—C8—H8 | 119.6 | C17—C18—H18C | 109.5 |
C10—C9—C8 | 121.01 (19) | H18A—C18—H18C | 109.5 |
C10—C9—H9 | 119.5 | H18B—C18—H18C | 109.5 |
C8—C9—H9 | 119.5 | O5—C19—N1 | 121.59 (16) |
C11—C10—C9 | 119.50 (19) | O5—C19—C20 | 121.71 (16) |
C11—C10—H10 | 120.2 | N1—C19—C20 | 116.69 (15) |
C9—C10—H10 | 120.2 | C19—C20—H20A | 109.5 |
C10—C11—C12 | 120.2 (2) | C19—C20—H20B | 109.5 |
C10—C11—H11 | 119.9 | H20A—C20—H20B | 109.5 |
C12—C11—H11 | 119.9 | C19—C20—H20C | 109.5 |
C7—C12—C11 | 120.77 (17) | H20A—C20—H20C | 109.5 |
C7—C12—C13 | 120.28 (15) | H20B—C20—H20C | 109.5 |
| | | |
C6—C1—C2—C3 | 0.1 (3) | C2—C1—C14—O1 | −24.4 (2) |
C14—C1—C2—C3 | −177.39 (15) | C6—C1—C14—O1 | 158.16 (14) |
C1—C2—C3—C4 | 1.0 (3) | C2—C1—C14—C13 | −148.80 (15) |
C2—C3—C4—C5 | −1.1 (3) | C6—C1—C14—C13 | 33.76 (19) |
C3—C4—C5—C6 | 0.3 (3) | C2—C1—C14—C15 | 92.55 (17) |
C4—C5—C6—C1 | 0.7 (3) | C6—C1—C14—C15 | −84.88 (17) |
C4—C5—C6—C7 | −175.00 (17) | O2—C13—C14—O1 | 13.2 (2) |
C2—C1—C6—C5 | −0.9 (2) | C12—C13—C14—O1 | −166.31 (14) |
C14—C1—C6—C5 | 176.52 (15) | O2—C13—C14—C1 | 137.96 (16) |
C2—C1—C6—C7 | 174.93 (15) | C12—C13—C14—C1 | −41.58 (18) |
C14—C1—C6—C7 | −7.6 (2) | O2—C13—C14—C15 | −103.22 (18) |
C5—C6—C7—C12 | 162.48 (16) | C12—C13—C14—C15 | 77.25 (17) |
C1—C6—C7—C12 | −13.2 (2) | C19—N1—C15—C16 | −98.40 (18) |
C5—C6—C7—C8 | −13.1 (3) | C19—N1—C15—C14 | 138.77 (16) |
C1—C6—C7—C8 | 171.21 (16) | O1—C14—C15—N1 | 74.20 (17) |
C12—C7—C8—C9 | −1.0 (3) | C1—C14—C15—N1 | −46.52 (17) |
C6—C7—C8—C9 | 174.70 (17) | C13—C14—C15—N1 | −165.92 (13) |
C7—C8—C9—C10 | −0.9 (3) | O1—C14—C15—C16 | −49.35 (16) |
C8—C9—C10—C11 | 1.3 (3) | C1—C14—C15—C16 | −170.07 (12) |
C9—C10—C11—C12 | 0.1 (3) | C13—C14—C15—C16 | 70.53 (16) |
C8—C7—C12—C11 | 2.4 (2) | C17—O4—C16—O3 | −8.3 (2) |
C6—C7—C12—C11 | −173.42 (15) | C17—O4—C16—C15 | 171.44 (14) |
C8—C7—C12—C13 | 179.90 (16) | N1—C15—C16—O3 | −23.2 (2) |
C6—C7—C12—C13 | 4.1 (2) | C14—C15—C16—O3 | 100.97 (18) |
C10—C11—C12—C7 | −2.0 (3) | N1—C15—C16—O4 | 157.11 (13) |
C10—C11—C12—C13 | −179.55 (16) | C14—C15—C16—O4 | −78.72 (16) |
C7—C12—C13—O2 | −154.82 (18) | C16—O4—C17—C18 | 174.21 (18) |
C11—C12—C13—O2 | 22.7 (3) | C15—N1—C19—O5 | 1.9 (3) |
C7—C12—C13—C14 | 24.7 (2) | C15—N1—C19—C20 | −177.39 (16) |
C11—C12—C13—C14 | −157.76 (15) | | |
Hydrogen-bond geometry (Å, º) top
D—H···A | D—H | H···A | D···A | D—H···A |
O1—H1A···O5i | 0.85 (3) | 2.02 (3) | 2.850 (2) | 167 (2) |
N1—H2A···O3ii | 0.77 (2) | 2.36 (2) | 3.106 (2) | 164 (2) |
C20—H20C···O1ii | 0.96 | 2.43 | 3.343 (3) | 159 |
Symmetry codes: (i) x−1, y, z; (ii) −x+2, −y, −z. |