4,5-Diazafluoren-9-ol

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.

Computing details

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

Crystal data

C11H8N2O	F(000) = 768
Mr = 184.19	Dx = 1.380 Mg m^−3
Monoclinic, P21/n	Mo Kα radiation, λ = 0.71073 Å
a = 10.193 (2) Å	Cell parameters from 25 reflections
b = 14.477 (3) Å	θ = 2.4–10.2°
c = 12.092 (2) Å	µ = 0.09 mm^−1
β = 96.29 (3)°	T = 293 K
V = 1773.6 (6) Å^3	Block, colourless
Z = 8	0.28 × 0.24 × 0.22 mm

Data collection

Enraf-Nonius CAD4 diffractometer	Rint = 0.033
Radiation source: fine-focus sealed tube	θmax = 25.0°, θmin = 2.2°
Graphite monochromator	h = 0→12
2θ/ω scans	k = 0→17
3295 measured reflections	l = −14→14
3109 independent reflections	3 standard reflections every 97 reflections
1443 reflections with I > 2σ(I)	intensity decay: 5.0%

Refinement

Refinement on F^2	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F^2 > 2σ(F^2)] = 0.037	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.085	H atoms treated by a mixture of independent and constrained refinement
S = 1.02	w = 1/[σ^2(Fo^2) + (0.025P)^2] where P = (Fo^2 + 2Fc^2)/3
3109 reflections	(Δ/σ)max < 0.001
266 parameters	Δρmax = 0.11 e Å^−3
0 restraints	Δρmin = −0.19 e Å^−3

Special details

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 (Ų)

	x	y	z	Uiso*/Ueq	Occ. (<1)
C1	0.1262 (2)	0.45384 (15)	0.93918 (16)	0.0417 (5)
C2	0.0374 (2)	0.41417 (15)	0.85835 (17)	0.0463 (6)
C3	0.0054 (2)	0.46088 (19)	0.76034 (19)	0.0629 (7)
H3A	−0.0558	0.4358	0.7020	0.075*
C4	0.0656 (3)	0.5457 (2)	0.7488 (2)	0.0671 (7)
H4A	0.0466	0.5806	0.6814	0.081*
C5	0.1525 (2)	0.57974 (16)	0.8342 (2)	0.0606 (7)
H5A	0.1922	0.6388	0.8238	0.073*
C6	0.14554 (19)	0.39007 (14)	1.03424 (16)	0.0392 (5)
C7	0.0687 (2)	0.31250 (15)	1.00929 (17)	0.0444 (6)
C8	0.0764 (2)	0.24097 (15)	1.08495 (19)	0.0536 (6)
H8A	0.0250	0.1858	1.0710	0.064*
C9	0.1592 (2)	0.25122 (16)	1.18174 (19)	0.0573 (6)
H9A	0.1668	0.2030	1.2366	0.069*
C10	0.2316 (2)	0.33099 (16)	1.19963 (18)	0.0523 (6)
H10A	0.2893	0.3361	1.2676	0.063*
C11	−0.0071 (2)	0.32089 (16)	0.89550 (18)	0.0539 (6)
H11A	−0.0997	0.3234	0.9033	0.065*
C12	−0.1384 (2)	0.26664 (16)	0.4496 (2)	0.0594 (7)
H12A	−0.1742	0.3197	0.4833	0.071*
C13	−0.0313 (3)	0.22343 (19)	0.5068 (2)	0.0636 (7)
H13A	0.0068	0.2474	0.5771	0.076*
C14	0.0213 (2)	0.14566 (18)	0.4627 (2)	0.0610 (7)
H14A	0.0960	0.1144	0.5010	0.073*
C15	−0.0372 (2)	0.11494 (15)	0.36150 (18)	0.0466 (6)
C16	−0.1434 (2)	0.16399 (15)	0.30909 (17)	0.0430 (5)
C17	−0.2844 (3)	0.1029 (2)	0.0277 (2)	0.0740 (8)
H17A	−0.3483	0.1229	−0.0316	0.089*
C18	−0.2117 (3)	0.0258 (2)	0.0097 (2)	0.0733 (8)
H18A	−0.2253	−0.0063	−0.0601	0.088*
C19	−0.1185 (2)	−0.00546 (17)	0.0924 (2)	0.0633 (7)
H19A	−0.0666	−0.0597	0.0828	0.076*
C20	−0.1026 (2)	0.04470 (16)	0.18962 (18)	0.0482 (6)
C21	−0.1820 (2)	0.12129 (15)	0.20023 (17)	0.0463 (6)
C22	−0.0033 (2)	0.03400 (16)	0.29115 (18)	0.0544 (6)
H22A	−0.0186	−0.0228	0.3285	0.065*
N1	0.18481 (17)	0.53560 (12)	0.93112 (15)	0.0509 (5)
N2	0.22650 (16)	0.40204 (12)	1.12768 (13)	0.0443 (5)
N3	−0.19693 (18)	0.23882 (13)	0.34989 (15)	0.0506 (5)
N4	−0.27329 (18)	0.15248 (13)	0.12244 (16)	0.0599 (6)
O1	0.0141 (2)	0.24641 (14)	0.82353 (16)	0.0670 (7)	0.866 (3)
H1A	0.098 (3)	0.243 (2)	0.816 (2)	0.089 (12)*	0.866 (3)
O1A	−0.1459 (11)	0.3192 (8)	0.8911 (8)	0.065 (4)*	0.134 (3)
H1AA	−0.1687	0.2662	0.9124	0.097*	0.134 (3)
O2	0.12671 (16)	0.03586 (12)	0.26173 (14)	0.0641 (5)
H2A	0.176 (3)	−0.0015 (19)	0.310 (2)	0.108 (11)*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
C1	0.0406 (13)	0.0416 (14)	0.0426 (13)	0.0037 (11)	0.0036 (11)	0.0008 (11)
C2	0.0378 (13)	0.0539 (15)	0.0471 (14)	0.0044 (12)	0.0042 (11)	0.0010 (12)
C3	0.0548 (16)	0.0811 (19)	0.0508 (16)	0.0072 (15)	−0.0025 (13)	0.0008 (14)
C4	0.0683 (18)	0.080 (2)	0.0543 (17)	0.0212 (16)	0.0117 (15)	0.0226 (15)
C5	0.0647 (17)	0.0547 (16)	0.0638 (17)	0.0104 (14)	0.0137 (14)	0.0165 (14)
C6	0.0373 (12)	0.0359 (13)	0.0448 (14)	−0.0001 (11)	0.0063 (11)	−0.0025 (11)
C7	0.0406 (13)	0.0431 (13)	0.0500 (14)	−0.0032 (11)	0.0067 (11)	−0.0029 (12)
C8	0.0556 (15)	0.0409 (14)	0.0661 (16)	−0.0117 (12)	0.0153 (13)	−0.0015 (13)
C9	0.0676 (17)	0.0441 (15)	0.0620 (16)	0.0018 (14)	0.0155 (14)	0.0125 (13)
C10	0.0524 (14)	0.0533 (16)	0.0504 (14)	0.0046 (14)	0.0024 (12)	0.0080 (13)
C11	0.0376 (14)	0.0611 (16)	0.0629 (16)	−0.0045 (13)	0.0049 (12)	−0.0117 (14)
C12	0.0650 (18)	0.0551 (15)	0.0603 (16)	−0.0081 (14)	0.0170 (14)	−0.0025 (14)
C13	0.0587 (17)	0.0785 (19)	0.0535 (16)	−0.0179 (16)	0.0060 (14)	−0.0029 (15)
C14	0.0481 (15)	0.081 (2)	0.0534 (16)	−0.0031 (14)	0.0028 (13)	0.0205 (14)
C15	0.0422 (13)	0.0527 (15)	0.0457 (14)	−0.0001 (12)	0.0088 (11)	0.0159 (12)
C16	0.0410 (13)	0.0451 (14)	0.0439 (13)	−0.0035 (12)	0.0090 (11)	0.0083 (11)
C17	0.0612 (17)	0.102 (2)	0.0558 (18)	0.0016 (18)	−0.0049 (13)	−0.0031 (17)
C18	0.0708 (18)	0.089 (2)	0.0610 (18)	−0.0027 (18)	0.0099 (15)	−0.0173 (16)
C19	0.0658 (18)	0.0531 (16)	0.0733 (18)	−0.0030 (14)	0.0184 (15)	−0.0051 (14)
C20	0.0465 (14)	0.0436 (14)	0.0557 (16)	−0.0035 (12)	0.0108 (12)	0.0083 (12)
C21	0.0428 (14)	0.0503 (15)	0.0464 (14)	−0.0010 (13)	0.0078 (12)	0.0090 (12)
C22	0.0504 (15)	0.0504 (15)	0.0640 (16)	0.0079 (13)	0.0143 (13)	0.0223 (13)
N1	0.0541 (12)	0.0419 (11)	0.0572 (13)	0.0025 (11)	0.0084 (10)	0.0078 (10)
N2	0.0435 (11)	0.0402 (11)	0.0487 (11)	−0.0002 (9)	0.0022 (9)	0.0046 (10)
N3	0.0532 (12)	0.0473 (12)	0.0525 (12)	0.0014 (10)	0.0114 (10)	0.0024 (10)
N4	0.0519 (13)	0.0756 (15)	0.0507 (12)	0.0080 (11)	−0.0012 (11)	0.0034 (11)
O1	0.0576 (15)	0.0719 (15)	0.0705 (14)	−0.0214 (12)	0.0017 (11)	−0.0231 (11)
O2	0.0518 (11)	0.0638 (12)	0.0790 (12)	0.0173 (9)	0.0172 (9)	0.0245 (10)

Geometric parameters (Å, º)

C1—N1	1.334 (2)	C12—C13	1.377 (3)
C1—C2	1.382 (3)	C12—H12A	0.9601
C1—C6	1.471 (3)	C13—C14	1.380 (3)
C2—C3	1.372 (3)	C13—H13A	0.9600
C2—C11	1.509 (3)	C14—C15	1.375 (3)
C3—C4	1.386 (3)	C14—H14A	0.9599
C3—H3A	0.9600	C15—C16	1.389 (3)
C4—C5	1.376 (3)	C15—C22	1.510 (3)
C4—H4A	0.9600	C16—N3	1.332 (2)
C5—N1	1.344 (2)	C16—C21	1.468 (3)
C5—H5A	0.9600	C17—N4	1.346 (3)
C6—N2	1.335 (2)	C17—C18	1.370 (3)
C6—C7	1.383 (3)	C17—H17A	0.9600
C7—C8	1.378 (3)	C18—C19	1.379 (3)
C7—C11	1.507 (3)	C18—H18A	0.9599
C8—C9	1.374 (3)	C19—C20	1.376 (3)
C8—H8A	0.9601	C19—H19A	0.9601
C9—C10	1.375 (3)	C20—C21	1.387 (3)
C9—H9A	0.9600	C20—C22	1.511 (3)
C10—N2	1.345 (2)	C21—N4	1.328 (2)
C10—H10A	0.9601	C22—O2	1.409 (3)
C11—O1A	1.410 (11)	C22—H22A	0.9600
C11—O1	1.417 (3)	O1—H1A	0.87 (3)
C11—H11A	0.9600	O1A—H1AA	0.8501
C12—N3	1.347 (3)	O2—H2A	0.91 (3)
N1—C1—C2	125.5 (2)	C13—C12—H12A	117.9
N1—C1—C6	126.2 (2)	C12—C13—C14	119.8 (2)
C2—C1—C6	108.3 (2)	C12—C13—H13A	120.1
C3—C2—C1	118.8 (2)	C14—C13—H13A	120.1
C3—C2—C11	130.3 (2)	C15—C14—C13	117.3 (2)
C1—C2—C11	110.8 (2)	C15—C14—H14A	121.4
C2—C3—C4	117.2 (2)	C13—C14—H14A	121.3
C2—C3—H3A	121.5	C14—C15—C16	118.8 (2)
C4—C3—H3A	121.3	C14—C15—C22	130.4 (2)
C5—C4—C3	119.8 (2)	C16—C15—C22	110.7 (2)
C5—C4—H4A	120.1	N3—C16—C15	125.3 (2)
C3—C4—H4A	120.1	N3—C16—C21	126.5 (2)
N1—C5—C4	124.1 (2)	C15—C16—C21	108.2 (2)
N1—C5—H5A	118.1	N4—C17—C18	125.0 (2)
C4—C5—H5A	117.8	N4—C17—H17A	117.5
N2—C6—C7	124.9 (2)	C18—C17—H17A	117.5
N2—C6—C1	126.7 (2)	C17—C18—C19	119.6 (2)
C7—C6—C1	108.4 (2)	C17—C18—H18A	120.4
C8—C7—C6	118.4 (2)	C19—C18—H18A	120.0
C8—C7—C11	130.7 (2)	C20—C19—C18	117.0 (2)
C6—C7—C11	110.8 (2)	C20—C19—H19A	121.3
C9—C8—C7	118.0 (2)	C18—C19—H19A	121.7
C9—C8—H8A	120.8	C19—C20—C21	119.1 (2)
C7—C8—H8A	121.2	C19—C20—C22	130.2 (2)
C8—C9—C10	119.6 (2)	C21—C20—C22	110.6 (2)
C8—C9—H9A	120.4	N4—C21—C20	125.3 (2)
C10—C9—H9A	120.0	N4—C21—C16	126.1 (2)
N2—C10—C9	124.0 (2)	C20—C21—C16	108.5 (2)
N2—C10—H10A	118.2	O2—C22—C15	114.0 (2)
C9—C10—H10A	117.9	O2—C22—C20	110.9 (2)
O1A—C11—O1	100.6 (5)	C15—C22—C20	101.7 (2)
O1A—C11—C7	116.4 (5)	O2—C22—H22A	110.0
O1—C11—C7	113.7 (2)	C15—C22—H22A	109.9
O1A—C11—C2	109.7 (5)	C20—C22—H22A	109.9
O1—C11—C2	115.3 (2)	C1—N1—C5	114.6 (2)
C7—C11—C2	101.7 (2)	C6—N2—C10	115.1 (2)
O1A—C11—H11A	8.4	C16—N3—C12	114.5 (2)
O1—C11—H11A	107.9	C21—N4—C17	114.1 (2)
C7—C11—H11A	109.0	C11—O1—H1A	109 (2)
C2—C11—H11A	109.1	C11—O1A—H11A	16.9
N3—C12—C13	124.3 (2)	C11—O1A—H1AA	108.1
N3—C12—H12A	117.9

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
O1—H1A···N3^i	0.87 (3)	2.10 (3)	2.936 (3)	160 (2)
O2—H2A···N2^ii	0.91 (3)	1.83 (3)	2.710 (2)	164 (2)
C9—H9A···O2^iii	0.96	2.48	3.292 (3)	142

Symmetry codes: (i) x+1/2, −y+1/2, z+1/2; (ii) −x+1/2, y−1/2, −z+3/2; (iii) x, y, z+1.