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The title compound, C11H8N2O, has two crystallographically independent mol­ecules in the crystal. Each mol­ecule is basically planar except for the O atom. The two N atoms in the mol­ecule show different behaviour as hydrogen-bonding acceptors. One of them is involved in intermolecular O—H...N hydrogen bonds which stabilize the crystal packing.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S0108270100009823/na1481sup1.cif
Contains datablocks I, global

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S0108270100009823/na1481Isup2.hkl
Contains datablock I

CCDC reference: 153887

Computing details top

Data collection: CAD-4 Software (Enraf-Nonius, 1989); cell refinement: CAD-4 Software; data reduction: CAD-4 Software; 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.

4,5-Diazafluoren-9-ol top
Crystal data top
C11H8N2OF(000) = 768
Mr = 184.19Dx = 1.380 Mg m3
Monoclinic, P21/nMo Kα radiation, λ = 0.71073 Å
a = 10.193 (2) ÅCell parameters from 25 reflections
b = 14.477 (3) Åθ = 2.4–10.2°
c = 12.092 (2) ŵ = 0.09 mm1
β = 96.29 (3)°T = 293 K
V = 1773.6 (6) Å3Block, colourless
Z = 80.28 × 0.24 × 0.22 mm
Data collection top
Enraf-Nonius CAD4
diffractometer
Rint = 0.033
Radiation source: fine-focus sealed tubeθmax = 25.0°, θmin = 2.2°
Graphite monochromatorh = 012
2θ/ω scansk = 017
3295 measured reflectionsl = 1414
3109 independent reflections3 standard reflections every 97 reflections
1443 reflections with I > 2σ(I) intensity decay: 5.0%
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)] = 0.037Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.085H atoms treated by a mixture of independent and constrained refinement
S = 1.02 w = 1/[σ2(Fo2) + (0.025P)2]
where P = (Fo2 + 2Fc2)/3
3109 reflections(Δ/σ)max < 0.001
266 parametersΔρmax = 0.11 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*/UeqOcc. (<1)
C10.1262 (2)0.45384 (15)0.93918 (16)0.0417 (5)
C20.0374 (2)0.41417 (15)0.85835 (17)0.0463 (6)
C30.0054 (2)0.46088 (19)0.76034 (19)0.0629 (7)
H3A0.05580.43580.70200.075*
C40.0656 (3)0.5457 (2)0.7488 (2)0.0671 (7)
H4A0.04660.58060.68140.081*
C50.1525 (2)0.57974 (16)0.8342 (2)0.0606 (7)
H5A0.19220.63880.82380.073*
C60.14554 (19)0.39007 (14)1.03424 (16)0.0392 (5)
C70.0687 (2)0.31250 (15)1.00929 (17)0.0444 (6)
C80.0764 (2)0.24097 (15)1.08495 (19)0.0536 (6)
H8A0.02500.18581.07100.064*
C90.1592 (2)0.25122 (16)1.18174 (19)0.0573 (6)
H9A0.16680.20301.23660.069*
C100.2316 (2)0.33099 (16)1.19963 (18)0.0523 (6)
H10A0.28930.33611.26760.063*
C110.0071 (2)0.32089 (16)0.89550 (18)0.0539 (6)
H11A0.09970.32340.90330.065*
C120.1384 (2)0.26664 (16)0.4496 (2)0.0594 (7)
H12A0.17420.31970.48330.071*
C130.0313 (3)0.22343 (19)0.5068 (2)0.0636 (7)
H13A0.00680.24740.57710.076*
C140.0213 (2)0.14566 (18)0.4627 (2)0.0610 (7)
H14A0.09600.11440.50100.073*
C150.0372 (2)0.11494 (15)0.36150 (18)0.0466 (6)
C160.1434 (2)0.16399 (15)0.30909 (17)0.0430 (5)
C170.2844 (3)0.1029 (2)0.0277 (2)0.0740 (8)
H17A0.34830.12290.03160.089*
C180.2117 (3)0.0258 (2)0.0097 (2)0.0733 (8)
H18A0.22530.00630.06010.088*
C190.1185 (2)0.00546 (17)0.0924 (2)0.0633 (7)
H19A0.06660.05970.08280.076*
C200.1026 (2)0.04470 (16)0.18962 (18)0.0482 (6)
C210.1820 (2)0.12129 (15)0.20023 (17)0.0463 (6)
C220.0033 (2)0.03400 (16)0.29115 (18)0.0544 (6)
H22A0.01860.02280.32850.065*
N10.18481 (17)0.53560 (12)0.93112 (15)0.0509 (5)
N20.22650 (16)0.40204 (12)1.12768 (13)0.0443 (5)
N30.19693 (18)0.23882 (13)0.34989 (15)0.0506 (5)
N40.27329 (18)0.15248 (13)0.12244 (16)0.0599 (6)
O10.0141 (2)0.24641 (14)0.82353 (16)0.0670 (7)0.866 (3)
H1A0.098 (3)0.243 (2)0.816 (2)0.089 (12)*0.866 (3)
O1A0.1459 (11)0.3192 (8)0.8911 (8)0.065 (4)*0.134 (3)
H1AA0.16870.26620.91240.097*0.134 (3)
O20.12671 (16)0.03586 (12)0.26173 (14)0.0641 (5)
H2A0.176 (3)0.0015 (19)0.310 (2)0.108 (11)*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
C10.0406 (13)0.0416 (14)0.0426 (13)0.0037 (11)0.0036 (11)0.0008 (11)
C20.0378 (13)0.0539 (15)0.0471 (14)0.0044 (12)0.0042 (11)0.0010 (12)
C30.0548 (16)0.0811 (19)0.0508 (16)0.0072 (15)0.0025 (13)0.0008 (14)
C40.0683 (18)0.080 (2)0.0543 (17)0.0212 (16)0.0117 (15)0.0226 (15)
C50.0647 (17)0.0547 (16)0.0638 (17)0.0104 (14)0.0137 (14)0.0165 (14)
C60.0373 (12)0.0359 (13)0.0448 (14)0.0001 (11)0.0063 (11)0.0025 (11)
C70.0406 (13)0.0431 (13)0.0500 (14)0.0032 (11)0.0067 (11)0.0029 (12)
C80.0556 (15)0.0409 (14)0.0661 (16)0.0117 (12)0.0153 (13)0.0015 (13)
C90.0676 (17)0.0441 (15)0.0620 (16)0.0018 (14)0.0155 (14)0.0125 (13)
C100.0524 (14)0.0533 (16)0.0504 (14)0.0046 (14)0.0024 (12)0.0080 (13)
C110.0376 (14)0.0611 (16)0.0629 (16)0.0045 (13)0.0049 (12)0.0117 (14)
C120.0650 (18)0.0551 (15)0.0603 (16)0.0081 (14)0.0170 (14)0.0025 (14)
C130.0587 (17)0.0785 (19)0.0535 (16)0.0179 (16)0.0060 (14)0.0029 (15)
C140.0481 (15)0.081 (2)0.0534 (16)0.0031 (14)0.0028 (13)0.0205 (14)
C150.0422 (13)0.0527 (15)0.0457 (14)0.0001 (12)0.0088 (11)0.0159 (12)
C160.0410 (13)0.0451 (14)0.0439 (13)0.0035 (12)0.0090 (11)0.0083 (11)
C170.0612 (17)0.102 (2)0.0558 (18)0.0016 (18)0.0049 (13)0.0031 (17)
C180.0708 (18)0.089 (2)0.0610 (18)0.0027 (18)0.0099 (15)0.0173 (16)
C190.0658 (18)0.0531 (16)0.0733 (18)0.0030 (14)0.0184 (15)0.0051 (14)
C200.0465 (14)0.0436 (14)0.0557 (16)0.0035 (12)0.0108 (12)0.0083 (12)
C210.0428 (14)0.0503 (15)0.0464 (14)0.0010 (13)0.0078 (12)0.0090 (12)
C220.0504 (15)0.0504 (15)0.0640 (16)0.0079 (13)0.0143 (13)0.0223 (13)
N10.0541 (12)0.0419 (11)0.0572 (13)0.0025 (11)0.0084 (10)0.0078 (10)
N20.0435 (11)0.0402 (11)0.0487 (11)0.0002 (9)0.0022 (9)0.0046 (10)
N30.0532 (12)0.0473 (12)0.0525 (12)0.0014 (10)0.0114 (10)0.0024 (10)
N40.0519 (13)0.0756 (15)0.0507 (12)0.0080 (11)0.0012 (11)0.0034 (11)
O10.0576 (15)0.0719 (15)0.0705 (14)0.0214 (12)0.0017 (11)0.0231 (11)
O20.0518 (11)0.0638 (12)0.0790 (12)0.0173 (9)0.0172 (9)0.0245 (10)
Geometric parameters (Å, º) top
C1—N11.334 (2)C12—C131.377 (3)
C1—C21.382 (3)C12—H12A0.9601
C1—C61.471 (3)C13—C141.380 (3)
C2—C31.372 (3)C13—H13A0.9600
C2—C111.509 (3)C14—C151.375 (3)
C3—C41.386 (3)C14—H14A0.9599
C3—H3A0.9600C15—C161.389 (3)
C4—C51.376 (3)C15—C221.510 (3)
C4—H4A0.9600C16—N31.332 (2)
C5—N11.344 (2)C16—C211.468 (3)
C5—H5A0.9600C17—N41.346 (3)
C6—N21.335 (2)C17—C181.370 (3)
C6—C71.383 (3)C17—H17A0.9600
C7—C81.378 (3)C18—C191.379 (3)
C7—C111.507 (3)C18—H18A0.9599
C8—C91.374 (3)C19—C201.376 (3)
C8—H8A0.9601C19—H19A0.9601
C9—C101.375 (3)C20—C211.387 (3)
C9—H9A0.9600C20—C221.511 (3)
C10—N21.345 (2)C21—N41.328 (2)
C10—H10A0.9601C22—O21.409 (3)
C11—O1A1.410 (11)C22—H22A0.9600
C11—O11.417 (3)O1—H1A0.87 (3)
C11—H11A0.9600O1A—H1AA0.8501
C12—N31.347 (3)O2—H2A0.91 (3)
N1—C1—C2125.5 (2)C13—C12—H12A117.9
N1—C1—C6126.2 (2)C12—C13—C14119.8 (2)
C2—C1—C6108.3 (2)C12—C13—H13A120.1
C3—C2—C1118.8 (2)C14—C13—H13A120.1
C3—C2—C11130.3 (2)C15—C14—C13117.3 (2)
C1—C2—C11110.8 (2)C15—C14—H14A121.4
C2—C3—C4117.2 (2)C13—C14—H14A121.3
C2—C3—H3A121.5C14—C15—C16118.8 (2)
C4—C3—H3A121.3C14—C15—C22130.4 (2)
C5—C4—C3119.8 (2)C16—C15—C22110.7 (2)
C5—C4—H4A120.1N3—C16—C15125.3 (2)
C3—C4—H4A120.1N3—C16—C21126.5 (2)
N1—C5—C4124.1 (2)C15—C16—C21108.2 (2)
N1—C5—H5A118.1N4—C17—C18125.0 (2)
C4—C5—H5A117.8N4—C17—H17A117.5
N2—C6—C7124.9 (2)C18—C17—H17A117.5
N2—C6—C1126.7 (2)C17—C18—C19119.6 (2)
C7—C6—C1108.4 (2)C17—C18—H18A120.4
C8—C7—C6118.4 (2)C19—C18—H18A120.0
C8—C7—C11130.7 (2)C20—C19—C18117.0 (2)
C6—C7—C11110.8 (2)C20—C19—H19A121.3
C9—C8—C7118.0 (2)C18—C19—H19A121.7
C9—C8—H8A120.8C19—C20—C21119.1 (2)
C7—C8—H8A121.2C19—C20—C22130.2 (2)
C8—C9—C10119.6 (2)C21—C20—C22110.6 (2)
C8—C9—H9A120.4N4—C21—C20125.3 (2)
C10—C9—H9A120.0N4—C21—C16126.1 (2)
N2—C10—C9124.0 (2)C20—C21—C16108.5 (2)
N2—C10—H10A118.2O2—C22—C15114.0 (2)
C9—C10—H10A117.9O2—C22—C20110.9 (2)
O1A—C11—O1100.6 (5)C15—C22—C20101.7 (2)
O1A—C11—C7116.4 (5)O2—C22—H22A110.0
O1—C11—C7113.7 (2)C15—C22—H22A109.9
O1A—C11—C2109.7 (5)C20—C22—H22A109.9
O1—C11—C2115.3 (2)C1—N1—C5114.6 (2)
C7—C11—C2101.7 (2)C6—N2—C10115.1 (2)
O1A—C11—H11A8.4C16—N3—C12114.5 (2)
O1—C11—H11A107.9C21—N4—C17114.1 (2)
C7—C11—H11A109.0C11—O1—H1A109 (2)
C2—C11—H11A109.1C11—O1A—H11A16.9
N3—C12—C13124.3 (2)C11—O1A—H1AA108.1
N3—C12—H12A117.9
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
O1—H1A···N3i0.87 (3)2.10 (3)2.936 (3)160 (2)
O2—H2A···N2ii0.91 (3)1.83 (3)2.710 (2)164 (2)
C9—H9A···O2iii0.962.483.292 (3)142
Symmetry codes: (i) x+1/2, y+1/2, z+1/2; (ii) x+1/2, y1/2, z+3/2; (iii) x, y, z+1.
 

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