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The title compound, C16H11NO3, contains two planar ring systems and, in the crystal structure, the asymmetric unit is composed of two mol­ecules. There are some intermolecular C—H...O hydrogen bonds and π–π stacking interactions.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536804005653/wn6221sup1.cif
Contains datablocks global, I

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536804005653/wn6221Isup2.hkl
Contains datablock I

CCDC reference: 238830

Key indicators

  • Single-crystal X-ray study
  • T = 298 K
  • Mean [sigma](C-C) = 0.003 Å
  • R factor = 0.051
  • wR factor = 0.127
  • Data-to-parameter ratio = 12.9

checkCIF/PLATON results

No syntax errors found



Alert level A PLAT707_ALERT_1_A D...A Calc 17.948(2), Rep 3.451(2), Dev.. 7248.50 Sigma C9 -O1 1.555 3.666 PLAT707_ALERT_1_A D...A Calc 18.330(2), Rep 3.506(2), Dev.. 7412.00 Sigma C9 -O4 1.555 1.555 PLAT707_ALERT_1_A D...A Calc 17.139(3), Rep 3.206(3), Dev.. 4644.33 Sigma C14 -O6 1.555 4.564 PLAT707_ALERT_1_A D...A Calc 22.840(3), Rep 3.214(3), Dev.. 6542.00 Sigma C30 -O3 1.555 4.555 PLAT726_ALERT_1_A H...A Calc 18.56750, Rep 2.59000 Dev... 15.98 Ang. H9A -O1 1.555 3.666 PLAT726_ALERT_1_A H...A Calc 18.61590, Rep 2.56000 Dev... 16.06 Ang. H9B -O4 1.555 1.555 PLAT726_ALERT_1_A H...A Calc 17.88460, Rep 2.59000 Dev... 15.29 Ang. H14 -O6 1.555 4.564 PLAT726_ALERT_1_A H...A Calc 22.15000, Rep 2.57000 Dev... 19.58 Ang. H30 -O3 1.555 4.555 PLAT728_ALERT_1_A D-H..A Calc 49.14, Rep 147.00 Dev... 97.86 Deg. C9 -H9A -O1 1.555 1.555 3.666 PLAT728_ALERT_1_A D-H..A Calc 71.39, Rep 165.00 Dev... 93.61 Deg. C9 -H9B -O4 1.555 1.555 1.555 PLAT728_ALERT_1_A D-H..A Calc 35.87, Rep 124.00 Dev... 88.13 Deg. C14 -H14 -O6 1.555 1.555 4.564 PLAT728_ALERT_1_A D-H..A Calc 137.08, Rep 127.00 Dev... 10.08 Deg. C30 -H30 -O3 1.555 1.555 4.555
Alert level C PLAT230_ALERT_2_C Hirshfeld Test Diff for C14 - C15 .. 5.57 su PLAT230_ALERT_2_C Hirshfeld Test Diff for C26 - C27 .. 5.03 su
12 ALERT level A = In general: serious problem 0 ALERT level B = Potentially serious problem 2 ALERT level C = Check and explain 0 ALERT level G = General alerts; check 12 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 0 ALERT type 3 Indicator that the structure quality may be low 0 ALERT type 4 Improvement, methodology, query or suggestion

Computing details top

Data collection: SMART (Bruker, 2002); cell refinement: SAINT (Bruker, 2002); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: XP (Bruker, 2002); software used to prepare material for publication: SHELXL97.

1-phenyl-2-phthalimidoethanone top
Crystal data top
C16H11NO3F(000) = 1104
Mr = 265.26Dx = 1.356 Mg m3
Monoclinic, P21/cMelting point: 446 K
Hall symbol: -P 2ybcMo Kα radiation, λ = 0.71073 Å
a = 12.8670 (5) ÅCell parameters from 648 reflections
b = 14.2568 (6) Åθ = 2.5–23.5°
c = 14.2196 (6) ŵ = 0.10 mm1
β = 94.728 (2)°T = 298 K
V = 2599.60 (18) Å3Block, colorless
Z = 80.39 × 0.35 × 0.32 mm
Data collection top
Bruker SMART APEX area-detector
diffractometer
4665 independent reflections
Radiation source: fine-focus sealed tube3520 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.020
φ and ω scansθmax = 25.2°, θmin = 1.6°
Absorption correction: multi-scan
(SADABS; Bruker, 2000)
h = 1515
Tmin = 0.963, Tmax = 0.974k = 1712
13485 measured reflectionsl = 1716
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)] = 0.051Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.127H-atom parameters constrained
S = 1.04 w = 1/[σ2(Fo2) + (0.0636P)2 + 0.3423P]
where P = (Fo2 + 2Fc2)/3
4665 reflections(Δ/σ)max < 0.001
361 parametersΔρmax = 0.15 e Å3
0 restraintsΔρmin = 0.24 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
O10.51631 (11)0.86804 (10)0.03907 (11)0.0728 (4)
O20.86323 (11)0.88937 (10)0.12847 (11)0.0713 (4)
O30.61001 (13)0.99092 (11)0.23022 (10)0.0839 (5)
O40.89942 (10)0.12473 (9)1.01796 (8)0.0597 (4)
O50.90628 (11)0.12087 (10)0.69854 (8)0.0627 (4)
O60.71791 (10)0.01113 (9)0.86403 (10)0.0673 (4)
N10.68809 (11)0.90227 (10)0.08326 (10)0.0508 (4)
N20.90024 (11)0.09980 (10)0.85838 (9)0.0468 (4)
C10.75111 (14)0.75244 (13)0.10202 (11)0.0492 (5)
C20.81148 (17)0.67303 (15)0.11784 (13)0.0616 (5)
H20.88250.67720.13550.074*
C30.7623 (2)0.58692 (15)0.10646 (14)0.0729 (6)
H30.80080.53220.11700.088*
C40.6569 (2)0.58116 (16)0.07966 (16)0.0792 (7)
H40.62570.52250.07250.095*
C50.59685 (18)0.66089 (15)0.06329 (15)0.0693 (6)
H50.52600.65680.04480.083*
C60.64549 (15)0.74605 (13)0.07530 (12)0.0512 (5)
C70.60365 (15)0.84237 (13)0.06299 (12)0.0526 (5)
C80.77938 (15)0.85352 (13)0.10808 (12)0.0506 (5)
C90.67890 (15)1.00328 (12)0.08164 (13)0.0532 (5)
H9A0.63211.02160.02780.064*
H9B0.74671.03040.07360.064*
C100.63858 (14)1.04269 (14)0.17023 (13)0.0544 (5)
C110.63689 (13)1.14659 (14)0.18053 (13)0.0530 (5)
C120.65836 (15)1.20681 (14)0.10846 (15)0.0601 (5)
H120.67351.18250.05040.072*
C130.65751 (18)1.30243 (15)0.12183 (18)0.0750 (6)
H130.67171.34210.07260.090*
C140.63607 (18)1.33956 (18)0.2064 (2)0.0830 (7)
H140.63541.40430.21460.100*
C150.61558 (18)1.28161 (19)0.2789 (2)0.0850 (8)
H150.60171.30690.33690.102*
C160.61545 (16)1.18453 (17)0.26654 (16)0.0724 (6)
H160.60101.14530.31600.087*
C170.89447 (15)0.33605 (13)0.95477 (13)0.0567 (5)
H170.89360.33631.02010.068*
C180.89316 (16)0.41883 (14)0.90369 (15)0.0639 (5)
H180.89170.47580.93530.077*
C190.89392 (15)0.41825 (14)0.80626 (15)0.0603 (5)
H190.89260.47480.77360.072*
C200.89657 (13)0.33468 (14)0.75667 (13)0.0521 (5)
H200.89690.33410.69130.063*
C210.89867 (13)0.25249 (12)0.80773 (11)0.0437 (4)
C220.89703 (13)0.25338 (12)0.90513 (12)0.0449 (4)
C230.89870 (13)0.15471 (13)0.93811 (12)0.0453 (4)
C240.90200 (13)0.15316 (13)0.77681 (12)0.0462 (4)
C250.90055 (14)0.00125 (13)0.86034 (13)0.0523 (5)
H25A0.94270.02250.91590.063*
H25B0.93210.02470.80530.063*
C260.79128 (14)0.04136 (13)0.86161 (11)0.0469 (4)
C270.77879 (13)0.14473 (12)0.85838 (11)0.0452 (4)
C280.86258 (15)0.20576 (13)0.87283 (12)0.0515 (5)
H280.92950.18200.88600.062*
C290.84737 (17)0.30123 (14)0.86774 (13)0.0616 (5)
H290.90410.34150.87780.074*
C300.74959 (18)0.33732 (15)0.84803 (13)0.0652 (6)
H300.73980.40190.84470.078*
C310.66597 (18)0.27805 (16)0.83320 (14)0.0661 (6)
H310.59950.30270.81930.079*
C320.67952 (15)0.18222 (15)0.83867 (12)0.0570 (5)
H320.62220.14260.82920.068*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
O10.0536 (9)0.0725 (10)0.0898 (10)0.0039 (7)0.0099 (7)0.0075 (8)
O20.0514 (9)0.0699 (10)0.0913 (11)0.0044 (7)0.0012 (7)0.0012 (8)
O30.1150 (13)0.0699 (10)0.0708 (9)0.0123 (9)0.0315 (9)0.0165 (8)
O40.0730 (9)0.0625 (9)0.0429 (7)0.0034 (7)0.0014 (6)0.0110 (6)
O50.0745 (9)0.0699 (9)0.0438 (7)0.0018 (7)0.0046 (6)0.0078 (7)
O60.0562 (8)0.0581 (9)0.0883 (10)0.0100 (7)0.0102 (7)0.0089 (7)
N10.0497 (9)0.0454 (9)0.0569 (9)0.0026 (7)0.0022 (7)0.0015 (7)
N20.0514 (9)0.0440 (9)0.0445 (8)0.0015 (7)0.0015 (6)0.0008 (7)
C10.0590 (12)0.0515 (12)0.0377 (9)0.0054 (9)0.0070 (8)0.0019 (8)
C20.0708 (13)0.0628 (14)0.0516 (11)0.0146 (11)0.0066 (9)0.0051 (10)
C30.109 (2)0.0507 (13)0.0597 (13)0.0173 (13)0.0086 (12)0.0055 (10)
C40.116 (2)0.0481 (13)0.0729 (15)0.0098 (13)0.0035 (14)0.0018 (11)
C50.0788 (15)0.0555 (14)0.0725 (14)0.0099 (11)0.0015 (11)0.0051 (11)
C60.0599 (12)0.0491 (12)0.0446 (10)0.0003 (9)0.0034 (8)0.0026 (8)
C70.0526 (12)0.0559 (12)0.0487 (10)0.0003 (9)0.0006 (8)0.0031 (9)
C80.0501 (11)0.0557 (12)0.0464 (10)0.0031 (9)0.0058 (8)0.0006 (9)
C90.0572 (11)0.0452 (11)0.0572 (11)0.0020 (9)0.0056 (9)0.0023 (9)
C100.0531 (11)0.0576 (13)0.0524 (11)0.0078 (9)0.0042 (9)0.0055 (10)
C110.0425 (10)0.0586 (13)0.0571 (11)0.0063 (9)0.0017 (8)0.0074 (10)
C120.0629 (13)0.0530 (13)0.0626 (12)0.0009 (10)0.0046 (10)0.0059 (10)
C130.0772 (15)0.0559 (14)0.0894 (17)0.0031 (12)0.0089 (12)0.0031 (13)
C140.0734 (16)0.0643 (16)0.108 (2)0.0039 (12)0.0104 (14)0.0227 (16)
C150.0716 (16)0.092 (2)0.0911 (18)0.0108 (14)0.0060 (13)0.0423 (16)
C160.0666 (14)0.0807 (17)0.0708 (14)0.0090 (12)0.0109 (11)0.0124 (12)
C170.0671 (13)0.0548 (12)0.0479 (10)0.0013 (10)0.0033 (9)0.0016 (9)
C180.0730 (14)0.0483 (12)0.0706 (14)0.0007 (10)0.0069 (11)0.0038 (10)
C190.0597 (12)0.0488 (12)0.0725 (14)0.0004 (9)0.0059 (10)0.0158 (10)
C200.0490 (11)0.0614 (13)0.0458 (10)0.0003 (9)0.0036 (8)0.0104 (9)
C210.0395 (9)0.0499 (11)0.0413 (9)0.0007 (8)0.0009 (7)0.0046 (8)
C220.0441 (10)0.0486 (11)0.0419 (9)0.0015 (8)0.0023 (7)0.0026 (8)
C230.0429 (10)0.0518 (11)0.0406 (10)0.0029 (8)0.0000 (7)0.0051 (8)
C240.0414 (10)0.0573 (12)0.0396 (10)0.0028 (8)0.0006 (7)0.0009 (8)
C250.0527 (11)0.0452 (11)0.0584 (11)0.0013 (8)0.0011 (8)0.0000 (9)
C260.0491 (10)0.0549 (12)0.0365 (9)0.0041 (9)0.0032 (7)0.0054 (8)
C270.0505 (10)0.0493 (11)0.0359 (9)0.0025 (8)0.0035 (7)0.0024 (8)
C280.0521 (11)0.0508 (12)0.0511 (10)0.0039 (9)0.0004 (8)0.0006 (9)
C290.0712 (14)0.0511 (12)0.0619 (12)0.0027 (10)0.0021 (10)0.0009 (10)
C300.0842 (16)0.0537 (13)0.0574 (12)0.0124 (12)0.0032 (11)0.0038 (10)
C310.0650 (14)0.0698 (15)0.0627 (13)0.0223 (12)0.0002 (10)0.0028 (11)
C320.0523 (11)0.0649 (14)0.0535 (11)0.0029 (10)0.0028 (9)0.0027 (10)
Geometric parameters (Å, º) top
O1—C71.204 (2)C13—H130.9300
O2—C81.207 (2)C14—C151.365 (3)
O3—C101.208 (2)C14—H140.9300
O4—C231.2125 (19)C15—C161.395 (3)
O5—C241.210 (2)C15—H150.9300
O6—C261.207 (2)C16—H160.9300
N1—C81.385 (2)C17—C221.376 (2)
N1—C71.393 (2)C17—C181.385 (3)
N1—C91.445 (2)C17—H170.9300
N2—C231.379 (2)C18—C191.386 (3)
N2—C241.389 (2)C18—H180.9300
N2—C251.441 (2)C19—C201.386 (3)
C1—C21.381 (3)C19—H190.9300
C1—C61.384 (3)C20—C211.378 (2)
C1—C81.487 (3)C20—H200.9300
C2—C31.385 (3)C21—C221.387 (2)
C2—H20.9300C21—C241.484 (2)
C3—C41.380 (3)C22—C231.482 (2)
C3—H30.9300C25—C261.519 (2)
C4—C51.383 (3)C25—H25A0.9700
C4—H40.9300C25—H25B0.9700
C5—C61.370 (3)C26—C271.483 (2)
C5—H50.9300C27—C281.387 (2)
C6—C71.480 (3)C27—C321.392 (2)
C9—C101.510 (3)C28—C291.376 (3)
C9—H9A0.9700C28—H280.9300
C9—H9B0.9700C29—C301.367 (3)
C10—C111.489 (3)C29—H290.9300
C11—C121.382 (3)C30—C311.371 (3)
C11—C161.386 (3)C30—H300.9300
C12—C131.377 (3)C31—C321.379 (3)
C12—H120.9300C31—H310.9300
C13—C141.362 (3)C32—H320.9300
C8—N1—C7112.05 (15)C11—C16—C15120.0 (2)
C8—N1—C9124.79 (15)C11—C16—H16120.0
C7—N1—C9123.11 (15)C15—C16—H16120.0
C23—N2—C24112.20 (15)C22—C17—C18117.44 (17)
C23—N2—C25123.49 (14)C22—C17—H17121.3
C24—N2—C25124.31 (15)C18—C17—H17121.3
C2—C1—C6121.15 (18)C17—C18—C19121.21 (19)
C2—C1—C8130.80 (19)C17—C18—H18119.4
C6—C1—C8108.04 (16)C19—C18—H18119.4
C1—C2—C3117.5 (2)C18—C19—C20121.06 (18)
C1—C2—H2121.2C18—C19—H19119.5
C3—C2—H2121.2C20—C19—H19119.5
C4—C3—C2120.9 (2)C21—C20—C19117.59 (17)
C4—C3—H3119.5C21—C20—H20121.2
C2—C3—H3119.5C19—C20—H20121.2
C3—C4—C5121.3 (2)C20—C21—C22121.16 (17)
C3—C4—H4119.3C20—C21—C24130.92 (16)
C5—C4—H4119.3C22—C21—C24107.92 (14)
C6—C5—C4117.6 (2)C17—C22—C21121.55 (16)
C6—C5—H5121.2C17—C22—C23130.62 (16)
C4—C5—H5121.2C21—C22—C23107.84 (15)
C5—C6—C1121.38 (19)O4—C23—N2124.77 (17)
C5—C6—C7130.50 (19)O4—C23—C22129.01 (17)
C1—C6—C7108.11 (16)N2—C23—C22106.22 (14)
O1—C7—N1124.46 (18)O5—C24—N2124.39 (17)
O1—C7—C6129.59 (18)O5—C24—C21129.80 (16)
N1—C7—C6105.93 (16)N2—C24—C21105.81 (14)
O2—C8—N1124.82 (18)N2—C25—C26112.05 (15)
O2—C8—C1129.32 (18)N2—C25—H25A109.2
N1—C8—C1105.86 (16)C26—C25—H25A109.2
N1—C9—C10113.02 (15)N2—C25—H25B109.2
N1—C9—H9A109.0C26—C25—H25B109.2
C10—C9—H9A109.0H25A—C25—H25B107.9
N1—C9—H9B109.0O6—C26—C27122.27 (17)
C10—C9—H9B109.0O6—C26—C25119.58 (17)
H9A—C9—H9B107.8C27—C26—C25118.14 (15)
O3—C10—C11122.05 (18)C28—C27—C32118.56 (17)
O3—C10—C9120.48 (18)C28—C27—C26122.53 (16)
C11—C10—C9117.47 (16)C32—C27—C26118.90 (16)
C12—C11—C16118.58 (19)C29—C28—C27120.46 (17)
C12—C11—C10122.66 (17)C29—C28—H28119.8
C16—C11—C10118.74 (19)C27—C28—H28119.8
C13—C12—C11120.6 (2)C30—C29—C28120.52 (19)
C13—C12—H12119.7C30—C29—H29119.7
C11—C12—H12119.7C28—C29—H29119.7
C14—C13—C12120.7 (2)C29—C30—C31119.8 (2)
C14—C13—H13119.6C29—C30—H30120.1
C12—C13—H13119.6C31—C30—H30120.1
C13—C14—C15119.9 (2)C30—C31—C32120.54 (19)
C13—C14—H14120.1C30—C31—H31119.7
C15—C14—H14120.1C32—C31—H31119.7
C14—C15—C16120.2 (2)C31—C32—C27120.11 (19)
C14—C15—H15119.9C31—C32—H32119.9
C16—C15—H15119.9C27—C32—H32119.9
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
C9—H9A···O1i0.972.593.451 (2)147
C9—H9B···O40.972.563.506 (2)165
C14—H14···O6ii0.932.593.206 (3)124
C15—H15···O1iii0.932.573.438 (3)155
C20—H20···O4iv0.932.543.447 (2)166
C30—H30···O3v0.932.573.214 (3)127
Symmetry codes: (i) x+1, y+1, z+1; (ii) x, y+1/2, z3/2; (iii) x+1, y+1/2, z+1/2; (iv) x, y+1/2, z1/2; (v) x, y1/2, z1/2.
 

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