The crystal structure of the title compound, C
13H
10O
2N
2, is stabilized by N—H
N intermolecular hydrogen bonds which generate
C(4) chains. The phthalide system is planar and the dihedral angle between this plane and that of the pyridine ring is 73.55 (13)°.
Supporting information
CCDC reference: 608426
Key indicators
- Single-crystal X-ray study
- T = 296 K
- Mean (C-C) = 0.005 Å
- R factor = 0.062
- wR factor = 0.132
- Data-to-parameter ratio = 12.6
checkCIF/PLATON results
No syntax errors found
Alert level B
RINTA01_ALERT_3_B The value of Rint is greater than 0.15
Rint given 0.154
PLAT020_ALERT_3_B The value of Rint is greater than 0.10 ......... 0.15
Alert level C
PLAT063_ALERT_3_C Crystal Probably too Large for Beam Size ....... 0.78 mm
PLAT340_ALERT_3_C Low Bond Precision on C-C bonds (x 1000) Ang ... 5
0 ALERT level A = In general: serious problem
2 ALERT level B = Potentially serious problem
2 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
4 ALERT type 3 Indicator that the structure quality may be low
0 ALERT type 4 Improvement, methodology, query or suggestion
Data collection: X-AREA (Stoe & Cie, 2002); cell refinement: X-AREA; data reduction: X-RED32 (Stoe & Cie, 2002); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997); software used to prepare material for publication: WinGX (Farrugia, 1999).
3-(2-pyridylamino)isobenzofuran-1(3
H)-one
top
Crystal data top
C13H10N2O2 | F(000) = 944 |
Mr = 226.23 | Dx = 1.333 Mg m−3 |
Orthorhombic, Pbca | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: -P 2ac 2ab | Cell parameters from 21419 reflections |
a = 8.6366 (5) Å | θ = 2.3–27.2° |
b = 18.1462 (12) Å | µ = 0.09 mm−1 |
c = 14.3885 (11) Å | T = 296 K |
V = 2255.0 (3) Å3 | Prismatic stick, colorless |
Z = 8 | 0.78 × 0.31 × 0.04 mm |
Data collection top
Stoe IPDS-2 diffractometer | 1991 independent reflections |
Radiation source: sealed X-ray tube, 12 x 0.4 mm long-fine focus | 1173 reflections with I > 2σ(I) |
Plane graphite monochromator | Rint = 0.154 |
Detector resolution: 6.67 pixels mm-1 | θmax = 25.0°, θmin = 2.2° |
ω scan rotation method | h = −10→9 |
Absorption correction: integration (X-RED32; Stoe & Cie, 2002) | k = −21→21 |
Tmin = 0.961, Tmax = 0.996 | l = −17→17 |
23991 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)] = 0.062 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.132 | H atoms treated by a mixture of independent and constrained refinement |
S = 1.04 | w = 1/[σ2(Fo2) + (0.0522P)2 + 0.1489P] where P = (Fo2 + 2Fc2)/3 |
1991 reflections | (Δ/σ)max < 0.001 |
158 parameters | Δρmax = 0.16 e Å−3 |
0 restraints | Δρmin = −0.18 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 | |
C1 | 0.3523 (5) | 0.54681 (18) | 0.0607 (3) | 0.0628 (9) | |
C2 | 0.2590 (4) | 0.48496 (17) | 0.0953 (2) | 0.0529 (8) | |
C3 | 0.1734 (5) | 0.4340 (2) | 0.0462 (3) | 0.0728 (11) | |
H3 | 0.1684 | 0.4352 | −0.0184 | 0.087* | |
C4 | 0.0950 (5) | 0.3810 (2) | 0.0971 (3) | 0.0797 (11) | |
H4 | 0.0356 | 0.3459 | 0.0663 | 0.096* | |
C5 | 0.1038 (4) | 0.37948 (18) | 0.1928 (3) | 0.0676 (10) | |
H5 | 0.0512 | 0.3429 | 0.2252 | 0.081* | |
C6 | 0.1892 (4) | 0.43105 (16) | 0.2414 (2) | 0.0541 (8) | |
H6 | 0.1945 | 0.4301 | 0.3060 | 0.065* | |
C7 | 0.2665 (4) | 0.48422 (16) | 0.1904 (2) | 0.0439 (7) | |
C8 | 0.3644 (4) | 0.54791 (16) | 0.2221 (2) | 0.0484 (8) | |
H8 | 0.4551 | 0.5294 | 0.2557 | 0.058* | |
C9 | 0.3543 (4) | 0.65661 (15) | 0.3229 (2) | 0.0438 (7) | |
C10 | 0.2658 (4) | 0.71041 (16) | 0.3667 (2) | 0.0527 (8) | |
H10 | 0.1583 | 0.7076 | 0.3661 | 0.063* | |
C11 | 0.3390 (4) | 0.76759 (18) | 0.4107 (2) | 0.0610 (9) | |
H11 | 0.2817 | 0.8043 | 0.4398 | 0.073* | |
C12 | 0.4991 (4) | 0.77010 (18) | 0.4112 (2) | 0.0609 (9) | |
H12 | 0.5517 | 0.8085 | 0.4402 | 0.073* | |
C13 | 0.5774 (4) | 0.71443 (17) | 0.3679 (2) | 0.0563 (8) | |
H13 | 0.6851 | 0.7158 | 0.3692 | 0.068* | |
N1 | 0.2816 (3) | 0.59796 (14) | 0.27937 (19) | 0.0495 (7) | |
N2 | 0.5097 (3) | 0.65780 (14) | 0.32353 (18) | 0.0506 (7) | |
O1 | 0.3760 (4) | 0.56746 (14) | −0.01803 (18) | 0.0930 (10) | |
O2 | 0.4143 (3) | 0.58324 (11) | 0.13471 (16) | 0.0620 (6) | |
H1 | 0.188 (5) | 0.6079 (18) | 0.256 (3) | 0.075 (11)* | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
C1 | 0.077 (2) | 0.0549 (19) | 0.056 (2) | 0.0063 (19) | 0.0094 (19) | −0.0003 (17) |
C2 | 0.064 (2) | 0.0473 (17) | 0.0473 (19) | 0.0008 (16) | 0.0000 (18) | −0.0033 (15) |
C3 | 0.098 (3) | 0.066 (2) | 0.055 (2) | −0.002 (2) | −0.014 (2) | −0.0116 (18) |
C4 | 0.087 (3) | 0.063 (2) | 0.088 (3) | −0.017 (2) | −0.009 (3) | −0.016 (2) |
C5 | 0.072 (3) | 0.0522 (19) | 0.079 (3) | −0.0092 (18) | 0.011 (2) | −0.0015 (17) |
C6 | 0.057 (2) | 0.0505 (17) | 0.0551 (19) | −0.0014 (15) | 0.0038 (16) | 0.0012 (16) |
C7 | 0.0410 (17) | 0.0457 (16) | 0.0449 (18) | 0.0052 (13) | −0.0011 (15) | −0.0049 (13) |
C8 | 0.0463 (18) | 0.0481 (16) | 0.0508 (19) | 0.0003 (14) | 0.0029 (15) | −0.0042 (14) |
C9 | 0.0399 (17) | 0.0487 (17) | 0.0427 (17) | −0.0027 (14) | 0.0012 (15) | 0.0000 (13) |
C10 | 0.0455 (19) | 0.0567 (18) | 0.0560 (19) | 0.0026 (15) | 0.0041 (17) | −0.0069 (16) |
C11 | 0.068 (3) | 0.056 (2) | 0.060 (2) | 0.0027 (18) | 0.0044 (19) | −0.0118 (16) |
C12 | 0.069 (2) | 0.053 (2) | 0.061 (2) | −0.0091 (18) | −0.0036 (19) | −0.0107 (16) |
C13 | 0.0465 (19) | 0.0630 (19) | 0.0595 (19) | −0.0084 (16) | −0.0045 (18) | −0.0095 (17) |
N1 | 0.0393 (15) | 0.0532 (15) | 0.0561 (17) | 0.0009 (13) | −0.0049 (13) | −0.0100 (12) |
N2 | 0.0433 (16) | 0.0551 (15) | 0.0534 (16) | −0.0016 (12) | −0.0013 (13) | −0.0062 (12) |
O1 | 0.146 (3) | 0.0720 (16) | 0.0608 (16) | −0.0013 (17) | 0.0232 (18) | 0.0143 (13) |
O2 | 0.0650 (15) | 0.0551 (12) | 0.0657 (14) | −0.0089 (11) | 0.0159 (13) | −0.0022 (11) |
Geometric parameters (Å, º) top
C1—O1 | 1.211 (4) | C8—O2 | 1.476 (4) |
C1—O2 | 1.363 (4) | C8—H8 | 0.9800 |
C1—C2 | 1.468 (5) | C9—N2 | 1.343 (4) |
C2—C7 | 1.370 (4) | C9—N1 | 1.385 (4) |
C2—C3 | 1.378 (5) | C9—C10 | 1.390 (4) |
C3—C4 | 1.386 (5) | C10—C11 | 1.370 (4) |
C3—H3 | 0.9300 | C10—H10 | 0.9300 |
C4—C5 | 1.378 (5) | C11—C12 | 1.383 (5) |
C4—H4 | 0.9300 | C11—H11 | 0.9300 |
C5—C6 | 1.382 (5) | C12—C13 | 1.366 (5) |
C5—H5 | 0.9300 | C12—H12 | 0.9300 |
C6—C7 | 1.384 (4) | C13—N2 | 1.344 (4) |
C6—H6 | 0.9300 | C13—H13 | 0.9300 |
C7—C8 | 1.503 (4) | N1—H1 | 0.89 (4) |
C8—N1 | 1.419 (4) | | |
| | | |
O1—C1—O2 | 120.9 (3) | N1—C8—H8 | 109.6 |
O1—C1—C2 | 130.3 (4) | O2—C8—H8 | 109.6 |
O2—C1—C2 | 108.8 (3) | C7—C8—H8 | 109.6 |
C7—C2—C3 | 122.0 (3) | N2—C9—N1 | 117.9 (3) |
C7—C2—C1 | 108.7 (3) | N2—C9—C10 | 122.4 (3) |
C3—C2—C1 | 129.3 (3) | N1—C9—C10 | 119.7 (3) |
C2—C3—C4 | 117.1 (3) | C11—C10—C9 | 119.2 (3) |
C2—C3—H3 | 121.4 | C11—C10—H10 | 120.4 |
C4—C3—H3 | 121.4 | C9—C10—H10 | 120.4 |
C5—C4—C3 | 121.0 (4) | C10—C11—C12 | 119.2 (3) |
C5—C4—H4 | 119.5 | C10—C11—H11 | 120.4 |
C3—C4—H4 | 119.5 | C12—C11—H11 | 120.4 |
C4—C5—C6 | 121.4 (4) | C13—C12—C11 | 117.9 (3) |
C4—C5—H5 | 119.3 | C13—C12—H12 | 121.0 |
C6—C5—H5 | 119.3 | C11—C12—H12 | 121.0 |
C5—C6—C7 | 117.4 (3) | N2—C13—C12 | 124.5 (3) |
C5—C6—H6 | 121.3 | N2—C13—H13 | 117.7 |
C7—C6—H6 | 121.3 | C12—C13—H13 | 117.7 |
C2—C7—C6 | 121.0 (3) | C9—N1—C8 | 121.7 (3) |
C2—C7—C8 | 108.8 (3) | C9—N1—H1 | 115 (2) |
C6—C7—C8 | 130.2 (3) | C8—N1—H1 | 112 (2) |
N1—C8—O2 | 111.3 (2) | C9—N2—C13 | 116.8 (3) |
N1—C8—C7 | 112.6 (3) | C1—O2—C8 | 109.9 (2) |
O2—C8—C7 | 103.8 (2) | | |
| | | |
O1—C1—C2—C7 | −179.4 (4) | C6—C7—C8—O2 | 179.5 (3) |
O2—C1—C2—C7 | −0.4 (4) | N2—C9—C10—C11 | 1.3 (5) |
O1—C1—C2—C3 | −0.1 (7) | N1—C9—C10—C11 | 179.1 (3) |
O2—C1—C2—C3 | 178.9 (3) | C9—C10—C11—C12 | −0.6 (5) |
C7—C2—C3—C4 | −0.5 (6) | C10—C11—C12—C13 | −0.5 (5) |
C1—C2—C3—C4 | −179.7 (4) | C11—C12—C13—N2 | 1.0 (5) |
C2—C3—C4—C5 | −0.4 (6) | N2—C9—N1—C8 | −11.8 (4) |
C3—C4—C5—C6 | 0.8 (6) | C10—C9—N1—C8 | 170.4 (3) |
C4—C5—C6—C7 | −0.4 (5) | O2—C8—N1—C9 | −69.9 (4) |
C3—C2—C7—C6 | 1.0 (5) | C7—C8—N1—C9 | 173.9 (3) |
C1—C2—C7—C6 | −179.7 (3) | N1—C9—N2—C13 | −178.6 (3) |
C3—C2—C7—C8 | −178.2 (3) | C10—C9—N2—C13 | −0.8 (5) |
C1—C2—C7—C8 | 1.1 (4) | C12—C13—N2—C9 | −0.3 (5) |
C5—C6—C7—C2 | −0.5 (5) | O1—C1—O2—C8 | 178.6 (3) |
C5—C6—C7—C8 | 178.5 (3) | C2—C1—O2—C8 | −0.5 (4) |
C2—C7—C8—N1 | 119.2 (3) | N1—C8—O2—C1 | −120.3 (3) |
C6—C7—C8—N1 | −59.9 (4) | C7—C8—O2—C1 | 1.1 (3) |
C2—C7—C8—O2 | −1.4 (3) | | |
Hydrogen-bond geometry (Å, º) top
D—H···A | D—H | H···A | D···A | D—H···A |
N1—H1···N2i | 0.89 (4) | 2.12 (4) | 2.981 (4) | 161 (3) |
Symmetry code: (i) x−1/2, y, −z+1/2. |