An instance of tandem hydrogen bonding: the geometry of indan-1,2-dione 2-oxime in the solid state

The title compound, C₉H₇NO₂, adopts a planar geometry in the solid state and forms tandem hydrogen-bonded dimers.

Key indicators

• Single-crystal X-ray study
• T = 300 K
• Mean [sigma](C-C) = 0.003 Å
• R factor = 0.044
• wR factor = 0.107
• Data-to-parameter ratio = 11.7

checkCIF/PLATON results

No syntax errors found



Alert level B
PLAT031_ALERT_4_B Refined Extinction Parameter within Range ......       2.40 Sigma

Alert level C
PLAT125_ALERT_4_C No _symmetry_space_group_name_Hall Given .......          ?
PLAT355_ALERT_3_C Long    O-H Bond (0.82A)   O1     -   H1     ...       1.04 Ang.
PLAT790_ALERT_4_C Centre of Gravity not Within Unit Cell: Resd.  #          1
              C9 H7 N O2

   0 ALERT level A = In general: serious problem
   1 ALERT level B = Potentially serious problem
   3 ALERT level C = Check and explain
   0 ALERT level G = General alerts; check

   0 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
   0 ALERT type 2 Indicator that the structure model may be wrong or deficient
   1 ALERT type 3 Indicator that the structure quality may be low
   3 ALERT type 4 Improvement, methodology, query or suggestion

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Computing details

Data collection: CrysAlis CCD (Oxford Diffraction, 2001); cell refinement: CrysAlis RED (Oxford Diffraction, 2001); data reduction: CrysAlis RED; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEP-3 (Farrugia,1997) and PLATON2002 (Spek,2002); software used to prepare material for publication: SHELXL97.

Indan-1,2-dione 2-oxime

Crystal data

C9H7NO2	Dx = 1.427 Mg m^−3
Mr = 161.16	Melting point: not meassured K
Monoclinic, P21/n	Mo Kα radiation, λ = 0.71073 Å
a = 6.169 (2) Å	Cell parameters from 1212 reflections
b = 5.410 (2) Å	θ = 6.8–49.0°
c = 22.606 (4) Å	µ = 0.10 mm^−1
β = 95.97 (2)°	T = 300 K
V = 750.4 (4) Å^3	Prism, brown
Z = 4	0.40 × 0.16 × 0.10 mm
F(000) = 336

Data collection

Oxford Diffraction Xcalibur CCD diffractometer	1075 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	Rint = 0.031
Graphite monochromator	θmax = 26.4°, θmin = 4.2°
Detector resolution: Sapphire CCD detector pixels mm^-1	h = −7→6
Rotation method data acquisition using ω scans	k = −6→6
4349 measured reflections	l = −28→24
1527 independent reflections

Refinement

Refinement on F^2	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: difference Fourier map
R[F^2 > 2σ(F^2)] = 0.044	Only H-atom coordinates refined
wR(F^2) = 0.107	w = 1/[σ^2(Fo^2) + (0.0524P)^2] where P = (Fo^2 + 2Fc^2)/3
S = 1.04	(Δ/σ)max = 0.004
1527 reflections	Δρmax = 0.14 e Å^−3
131 parameters	Δρmin = −0.13 e Å^−3
0 restraints	Extinction correction: SHELXL97, Fc^*=kFc[1+0.001xFc^2λ^3/sin(2θ)]^-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.012 (5)

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
C1	0.5660 (3)	0.0097 (3)	0.11794 (8)	0.0431 (5)
C2	0.4028 (3)	0.1021 (3)	0.06866 (8)	0.0403 (4)
C3	0.1987 (3)	−0.0472 (4)	0.06588 (9)	0.0426 (5)
H3A	0.166 (3)	−0.144 (4)	0.0282 (8)	0.051*
H3B	0.076 (3)	0.054 (3)	0.0726 (8)	0.051*
C4	0.2489 (3)	−0.2307 (3)	0.11549 (8)	0.0383 (4)
C5	0.4572 (3)	−0.1977 (3)	0.14462 (8)	0.0389 (4)
C6	0.5346 (3)	−0.3518 (4)	0.19155 (9)	0.0513 (5)
H6	0.671 (3)	−0.325 (4)	0.2095 (9)	0.062*
C7	0.4025 (3)	−0.5362 (4)	0.20887 (9)	0.0534 (5)
H7	0.450 (3)	−0.645 (4)	0.2411 (9)	0.064*
C8	0.1953 (3)	−0.5685 (4)	0.18000 (9)	0.0515 (5)
H8	0.108 (3)	−0.702 (4)	0.1934 (9)	0.062*
C9	0.1170 (3)	−0.4167 (3)	0.13363 (9)	0.0456 (5)
H9	−0.026 (3)	−0.443 (3)	0.1128 (8)	0.055*
N1	0.4495 (2)	0.2830 (3)	0.03618 (7)	0.0464 (4)
O1	0.2780 (2)	0.3383 (3)	−0.00737 (6)	0.0591 (4)
H1	0.345 (3)	0.488 (4)	−0.0274 (9)	0.071*
O2	0.7468 (2)	0.0928 (3)	0.13173 (7)	0.0630 (5)

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
C1	0.0355 (10)	0.0436 (10)	0.0512 (11)	−0.0028 (8)	0.0093 (8)	−0.0095 (9)
C2	0.0416 (10)	0.0374 (10)	0.0438 (10)	−0.0010 (8)	0.0126 (8)	−0.0044 (8)
C3	0.0397 (10)	0.0417 (11)	0.0465 (11)	−0.0032 (8)	0.0049 (9)	0.0015 (9)
C4	0.0388 (10)	0.0357 (9)	0.0416 (10)	−0.0014 (7)	0.0092 (8)	−0.0041 (8)
C5	0.0383 (9)	0.0385 (10)	0.0407 (10)	−0.0004 (8)	0.0072 (8)	−0.0041 (8)
C6	0.0466 (11)	0.0561 (12)	0.0497 (12)	0.0046 (10)	−0.0013 (9)	−0.0034 (10)
C7	0.0648 (13)	0.0497 (12)	0.0455 (12)	0.0065 (10)	0.0044 (10)	0.0076 (9)
C8	0.0619 (13)	0.0455 (12)	0.0496 (12)	−0.0055 (9)	0.0178 (10)	0.0036 (9)
C9	0.0433 (11)	0.0455 (11)	0.0487 (12)	−0.0064 (9)	0.0072 (9)	−0.0004 (9)
N1	0.0512 (9)	0.0426 (9)	0.0465 (9)	−0.0037 (7)	0.0101 (7)	−0.0010 (7)
O1	0.0636 (9)	0.0562 (9)	0.0560 (9)	−0.0119 (7)	−0.0007 (7)	0.0125 (7)
O2	0.0402 (8)	0.0633 (9)	0.0851 (11)	−0.0120 (6)	0.0048 (7)	−0.0054 (8)

Geometric parameters (Å, º)

C1—O2	1.2130 (19)	C5—C6	1.394 (3)
C1—C5	1.469 (2)	C6—C7	1.370 (3)
C1—C2	1.507 (2)	C6—H6	0.908 (19)
C2—N1	1.275 (2)	C7—C8	1.384 (3)
C2—C3	1.492 (2)	C7—H7	0.96 (2)
C3—C4	1.506 (2)	C8—C9	1.379 (3)
C3—H3A	1.000 (19)	C8—H8	0.97 (2)
C3—H3B	0.958 (18)	C9—H9	0.966 (18)
C4—C9	1.383 (2)	N1—O1	1.400 (2)
C4—C5	1.393 (2)	O1—H1	1.03 (2)
O2—C1—C5	128.67 (17)	C4—C5—C1	110.01 (16)
O2—C1—C2	126.35 (17)	C6—C5—C1	129.39 (17)
C5—C1—C2	104.97 (14)	C7—C6—C5	119.09 (18)
N1—C2—C3	129.21 (17)	C7—C6—H6	122.6 (13)
N1—C2—C1	120.45 (16)	C5—C6—H6	118.3 (13)
C3—C2—C1	110.34 (15)	C6—C7—C8	120.28 (19)
C2—C3—C4	102.61 (14)	C6—C7—H7	121.4 (12)
C2—C3—H3A	114.2 (10)	C8—C7—H7	118.3 (12)
C4—C3—H3A	107.3 (11)	C9—C8—C7	121.10 (19)
C2—C3—H3B	111.3 (11)	C9—C8—H8	121.2 (11)
C4—C3—H3B	111.3 (11)	C7—C8—H8	117.7 (11)
H3A—C3—H3B	109.9 (14)	C8—C9—C4	119.24 (18)
C9—C4—C5	119.69 (17)	C8—C9—H9	120.9 (11)
C9—C4—C3	128.24 (16)	C4—C9—H9	119.8 (11)
C5—C4—C3	112.07 (15)	C2—N1—O1	111.66 (14)
C4—C5—C6	120.60 (17)	N1—O1—H1	99.6 (11)
O2—C1—C2—N1	0.8 (3)	C2—C1—C5—C4	−0.24 (18)
C5—C1—C2—N1	−179.44 (15)	O2—C1—C5—C6	−0.9 (3)
O2—C1—C2—C3	−179.62 (18)	C2—C1—C5—C6	179.32 (17)
C5—C1—C2—C3	0.14 (18)	C4—C5—C6—C7	−0.2 (3)
N1—C2—C3—C4	179.54 (17)	C1—C5—C6—C7	−179.74 (17)
C1—C2—C3—C4	0.01 (19)	C5—C6—C7—C8	0.1 (3)
C2—C3—C4—C9	179.97 (17)	C6—C7—C8—C9	−0.2 (3)
C2—C3—C4—C5	−0.2 (2)	C7—C8—C9—C4	0.5 (3)
C9—C4—C5—C6	0.5 (3)	C5—C4—C9—C8	−0.7 (3)
C3—C4—C5—C6	−179.34 (17)	C3—C4—C9—C8	179.16 (18)
C9—C4—C5—C1	−179.86 (15)	C3—C2—N1—O1	−0.3 (3)
C3—C4—C5—C1	0.3 (2)	C1—C2—N1—O1	179.20 (14)
O2—C1—C5—C4	179.50 (18)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
O1—H1···N1^i	1.03 (2)	1.80 (2)	2.770 (2)	155.0 (16)

Symmetry code: (i) −x+1, −y+1, −z.