Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536807027523/hk2270sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S1600536807027523/hk2270Isup2.hkl |
CCDC reference: 654943
Key indicators
- Single-crystal X-ray study
- T = 296 K
- Mean (C-C) = 0.002 Å
- R factor = 0.038
- wR factor = 0.100
- Data-to-parameter ratio = 10.7
checkCIF/PLATON results
No syntax errors found
Alert level C PLAT063_ALERT_3_C Crystal Probably too Large for Beam Size ....... 0.65 mm PLAT480_ALERT_4_C Long H...A H-Bond Reported H5 .. N2 .. 2.65 Ang. PLAT480_ALERT_4_C Long H...A H-Bond Reported H6 .. O1 .. 2.84 Ang. PLAT480_ALERT_4_C Long H...A H-Bond Reported H6 .. O1 .. 2.84 Ang.
0 ALERT level A = In general: serious problem 0 ALERT level B = Potentially serious problem 4 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 0 ALERT type 5 Informative message, check
For general backgroud, see: Cheng et al. (1999); Allen et al. (1987). For related literature, see: Etter (1990).
A pure sample of the compound was obtained from Strides Arco Labs, Mangalore, India and crystallized from DMF (m.p. 528–530 K).
H atoms were located in difference syntheses and refined isotropically [N—H = 0.92 (2) Å, Uiso(H) = 0.078 (6) Å2; C—H = 0.942 (17)–0.975 (18) Å, Uiso(H) = 0.063 (5)–0.079 (5) Å2].
Phthalazines, also called benzo-orthodiazines or benzopyridazines, are a group of heterocyclic compounds isomeric with the cinnolines. The practical interest upon phthalazine derivatives is based on their widespread applications. Phthalazines, like other members of the isomeric diazine series, have found wide applications as therapeutic agents. Phthalazines are also commonly used as ligands in transition metal catalysis, as chemiluminescent materials and for optical applications (Cheng et al., 1999). 2-Substituted-8-(4,6-dimethoxy- pyrimidin-2-yloxy)-4-methylphthalazin-1-one derivatives are used as herbicides. In view of the importance of the title compound, (I), we herein report its crystal structure.
In the molecule of the title compound, (I), (Fig. 1), the bond lengths and angles are within normal ranges (Allen et al., 1987). The rings A (N1/N2/C1/C2/C7/C8) and B (C2—C7) are, of course, planar and they are also coplanar with a dihedral angle of A/B = 0.52 (7)°.
In the crystal structure, intermolecular N—H···O, C—H···N and C—H···O hydrogen bonds (Table 1) link the molecules, in which N—H···O bonds generate the centrosymmetric R22(8) dimers (Etter, 1990), and they are connected by C—H···O and C—H···N bonds to generate the edge-fussed [R32(8) R33(14)] ring motifs (Fig. 2). In addition, the three-dimensional network including these motifs are also linked by π···π interactions, occurring between the Cg1—Cg2 rings (Cg1 and Cg2 are the centroids of rings A and B) of the molecules at (x, y, z) and (x - 1, y, z), with a centroid-to-centroid distance of 3.588 (1) Å and a plane-to-plane separation of 3.434 Å.
For general backgroud, see: Cheng et al. (1999); Allen et al. (1987). For related literature, see: Etter (1990).
Data collection: X-AREA (Stoe & Cie, 2002); cell refinement: X-AREA; data reduction: X-RED (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).
C8H6N2O | F(000) = 304 |
Mr = 146.15 | Dx = 1.419 Mg m−3 |
Monoclinic, P21/c | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: -P 2ybc | Cell parameters from 9171 reflections |
a = 4.0321 (3) Å | θ = 3.0–27.9° |
b = 12.3412 (13) Å | µ = 0.10 mm−1 |
c = 13.7513 (10) Å | T = 296 K |
β = 90.534 (6)° | Prism, colorless |
V = 684.25 (10) Å3 | 0.65 × 0.46 × 0.29 mm |
Z = 4 |
Stoe IPDS II diffractometer | 1324 independent reflections |
Radiation source: sealed X-ray tube, 12 x 0.4 mm long-fine focus | 1064 reflections with I > 2σ(I) |
Plane graphite monochromator | Rint = 0.044 |
Detector resolution: 6.67 pixels mm-1 | θmax = 26.0°, θmin = 3.0° |
ω scans | h = −4→4 |
Absorption correction: integration (X-RED; Stoe & Cie, 2002) | k = −15→15 |
Tmin = 0.944, Tmax = 0.979 | l = −16→16 |
9171 measured reflections |
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)] = 0.038 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.100 | All H-atom parameters refined |
S = 1.06 | w = 1/[σ2(Fo2) + (0.0487P)2 + 0.0889P] where P = (Fo2 + 2Fc2)/3 |
1324 reflections | (Δ/σ)max < 0.001 |
124 parameters | Δρmax = 0.12 e Å−3 |
0 restraints | Δρmin = −0.16 e Å−3 |
C8H6N2O | V = 684.25 (10) Å3 |
Mr = 146.15 | Z = 4 |
Monoclinic, P21/c | Mo Kα radiation |
a = 4.0321 (3) Å | µ = 0.10 mm−1 |
b = 12.3412 (13) Å | T = 296 K |
c = 13.7513 (10) Å | 0.65 × 0.46 × 0.29 mm |
β = 90.534 (6)° |
Stoe IPDS II diffractometer | 1324 independent reflections |
Absorption correction: integration (X-RED; Stoe & Cie, 2002) | 1064 reflections with I > 2σ(I) |
Tmin = 0.944, Tmax = 0.979 | Rint = 0.044 |
9171 measured reflections |
R[F2 > 2σ(F2)] = 0.038 | 0 restraints |
wR(F2) = 0.100 | All H-atom parameters refined |
S = 1.06 | Δρmax = 0.12 e Å−3 |
1324 reflections | Δρmin = −0.16 e Å−3 |
124 parameters |
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. |
x | y | z | Uiso*/Ueq | ||
C1 | 0.8204 (4) | 0.04381 (11) | 0.86523 (10) | 0.0480 (4) | |
C2 | 0.7038 (3) | 0.08027 (11) | 0.77005 (9) | 0.0440 (3) | |
C3 | 0.5213 (4) | 0.01188 (13) | 0.70937 (11) | 0.0523 (4) | |
C4 | 0.4186 (4) | 0.04883 (16) | 0.62008 (12) | 0.0623 (4) | |
C5 | 0.4969 (5) | 0.15293 (16) | 0.58975 (12) | 0.0672 (5) | |
C6 | 0.6760 (4) | 0.22069 (15) | 0.64822 (12) | 0.0607 (4) | |
C7 | 0.7822 (4) | 0.18524 (12) | 0.74036 (10) | 0.0482 (4) | |
C8 | 0.9696 (4) | 0.25138 (12) | 0.80633 (12) | 0.0560 (4) | |
N1 | 0.9897 (3) | 0.11846 (10) | 0.91799 (9) | 0.0539 (3) | |
N2 | 1.0698 (3) | 0.22166 (10) | 0.89115 (10) | 0.0586 (4) | |
O1 | 0.7743 (3) | −0.04865 (8) | 0.89695 (8) | 0.0663 (4) | |
H1 | 1.074 (5) | 0.0989 (15) | 0.9782 (15) | 0.078 (6)* | |
H3 | 0.470 (4) | −0.0610 (15) | 0.7317 (13) | 0.063 (5)* | |
H4 | 0.291 (5) | 0.0011 (15) | 0.5808 (14) | 0.076 (5)* | |
H5 | 0.421 (5) | 0.1757 (15) | 0.5269 (15) | 0.079 (5)* | |
H6 | 0.728 (4) | 0.2924 (14) | 0.6304 (12) | 0.069 (5)* | |
H8 | 1.030 (4) | 0.3249 (15) | 0.7875 (12) | 0.063 (5)* |
U11 | U22 | U33 | U12 | U13 | U23 | |
C1 | 0.0569 (8) | 0.0442 (7) | 0.0428 (7) | 0.0024 (6) | −0.0040 (6) | 0.0005 (6) |
C2 | 0.0469 (7) | 0.0472 (7) | 0.0380 (7) | 0.0089 (6) | 0.0003 (5) | 0.0005 (5) |
C3 | 0.0547 (9) | 0.0567 (9) | 0.0455 (8) | 0.0057 (7) | −0.0029 (6) | −0.0031 (7) |
C4 | 0.0610 (10) | 0.0817 (12) | 0.0439 (8) | 0.0118 (8) | −0.0075 (7) | −0.0084 (8) |
C5 | 0.0710 (11) | 0.0895 (13) | 0.0410 (8) | 0.0258 (9) | −0.0023 (7) | 0.0093 (8) |
C6 | 0.0689 (10) | 0.0630 (10) | 0.0503 (9) | 0.0176 (8) | 0.0050 (7) | 0.0148 (7) |
C7 | 0.0502 (8) | 0.0481 (8) | 0.0463 (7) | 0.0115 (6) | 0.0055 (6) | 0.0046 (6) |
C8 | 0.0619 (9) | 0.0430 (8) | 0.0632 (9) | 0.0020 (7) | 0.0020 (7) | 0.0045 (7) |
N1 | 0.0704 (9) | 0.0481 (7) | 0.0430 (7) | −0.0025 (6) | −0.0099 (6) | 0.0015 (5) |
N2 | 0.0683 (9) | 0.0470 (7) | 0.0604 (8) | −0.0025 (6) | −0.0067 (6) | −0.0017 (6) |
O1 | 0.0955 (9) | 0.0494 (6) | 0.0536 (6) | −0.0116 (6) | −0.0212 (6) | 0.0114 (5) |
C1—O1 | 1.2363 (17) | C5—C6 | 1.363 (3) |
C1—N1 | 1.3533 (18) | C5—H5 | 0.96 (2) |
C1—C2 | 1.4580 (18) | C6—C7 | 1.404 (2) |
C2—C3 | 1.392 (2) | C6—H6 | 0.942 (17) |
C2—C7 | 1.395 (2) | C7—C8 | 1.431 (2) |
C3—C4 | 1.370 (2) | C8—N2 | 1.284 (2) |
C3—H3 | 0.973 (18) | C8—H8 | 0.975 (18) |
C4—C5 | 1.388 (3) | N1—N2 | 1.3656 (18) |
C4—H4 | 0.947 (19) | N1—H1 | 0.92 (2) |
O1—C1—N1 | 121.06 (13) | C4—C5—H5 | 118.1 (12) |
O1—C1—C2 | 123.59 (13) | C5—C6—C7 | 119.80 (16) |
N1—C1—C2 | 115.34 (12) | C5—C6—H6 | 122.7 (11) |
C3—C2—C7 | 120.49 (13) | C7—C6—H6 | 117.5 (11) |
C3—C2—C1 | 121.01 (13) | C2—C7—C6 | 119.04 (15) |
C7—C2—C1 | 118.50 (13) | C2—C7—C8 | 117.64 (13) |
C4—C3—C2 | 119.27 (15) | C6—C7—C8 | 123.32 (15) |
C4—C3—H3 | 121.8 (10) | N2—C8—C7 | 124.93 (14) |
C2—C3—H3 | 118.9 (10) | N2—C8—H8 | 115.4 (10) |
C3—C4—C5 | 120.64 (16) | C7—C8—H8 | 119.7 (10) |
C3—C4—H4 | 117.5 (12) | C1—N1—N2 | 127.55 (13) |
C5—C4—H4 | 121.8 (11) | C1—N1—H1 | 118.8 (12) |
C6—C5—C4 | 120.76 (15) | N2—N1—H1 | 113.6 (12) |
C6—C5—H5 | 121.1 (12) | C8—N2—N1 | 116.01 (13) |
O1—C1—C2—C3 | 1.9 (2) | C3—C2—C7—C8 | 179.84 (14) |
N1—C1—C2—C3 | −178.83 (14) | C1—C2—C7—C8 | −0.86 (19) |
O1—C1—C2—C7 | −177.44 (14) | C5—C6—C7—C2 | 0.5 (2) |
N1—C1—C2—C7 | 1.88 (19) | C5—C6—C7—C8 | −179.68 (15) |
C7—C2—C3—C4 | −0.2 (2) | C2—C7—C8—N2 | −0.4 (2) |
C1—C2—C3—C4 | −179.43 (13) | C6—C7—C8—N2 | 179.79 (15) |
C2—C3—C4—C5 | 0.5 (2) | O1—C1—N1—N2 | 177.40 (15) |
C3—C4—C5—C6 | −0.3 (3) | C2—C1—N1—N2 | −1.9 (2) |
C4—C5—C6—C7 | −0.2 (2) | C7—C8—N2—N1 | 0.5 (2) |
C3—C2—C7—C6 | −0.3 (2) | C1—N1—N2—C8 | 0.8 (2) |
C1—C2—C7—C6 | 178.96 (13) |
D—H···A | D—H | H···A | D···A | D—H···A |
N1—H1···O1i | 0.92 (2) | 1.92 (2) | 2.8423 (16) | 175.5 (17) |
C5—H5···N2ii | 0.96 (2) | 2.65 (2) | 3.568 (2) | 160.0 (15) |
C6—H6···O1iii | 0.942 (17) | 2.841 (17) | 3.4298 (19) | 121.6 (12) |
C6—H6···O1iv | 0.942 (17) | 2.835 (17) | 3.664 (2) | 147.5 (13) |
Symmetry codes: (i) −x+2, −y, −z+2; (ii) x−1, −y+1/2, z−1/2; (iii) −x+1, y+1/2, −z+3/2; (iv) −x+2, y+1/2, −z+3/2. |
Experimental details
Crystal data | |
Chemical formula | C8H6N2O |
Mr | 146.15 |
Crystal system, space group | Monoclinic, P21/c |
Temperature (K) | 296 |
a, b, c (Å) | 4.0321 (3), 12.3412 (13), 13.7513 (10) |
β (°) | 90.534 (6) |
V (Å3) | 684.25 (10) |
Z | 4 |
Radiation type | Mo Kα |
µ (mm−1) | 0.10 |
Crystal size (mm) | 0.65 × 0.46 × 0.29 |
Data collection | |
Diffractometer | Stoe IPDS II |
Absorption correction | Integration (X-RED; Stoe & Cie, 2002) |
Tmin, Tmax | 0.944, 0.979 |
No. of measured, independent and observed [I > 2σ(I)] reflections | 9171, 1324, 1064 |
Rint | 0.044 |
(sin θ/λ)max (Å−1) | 0.616 |
Refinement | |
R[F2 > 2σ(F2)], wR(F2), S | 0.038, 0.100, 1.06 |
No. of reflections | 1324 |
No. of parameters | 124 |
H-atom treatment | All H-atom parameters refined |
Δρmax, Δρmin (e Å−3) | 0.12, −0.16 |
Computer programs: X-AREA (Stoe & Cie, 2002), X-AREA, X-RED (Stoe & Cie, 2002), SHELXS97 (Sheldrick, 1997), SHELXL97 (Sheldrick, 1997), ORTEP-3 for Windows (Farrugia, 1997), WinGX (Farrugia, 1999).
D—H···A | D—H | H···A | D···A | D—H···A |
N1—H1···O1i | 0.92 (2) | 1.92 (2) | 2.8423 (16) | 175.5 (17) |
C5—H5···N2ii | 0.96 (2) | 2.65 (2) | 3.568 (2) | 160.0 (15) |
C6—H6···O1iii | 0.942 (17) | 2.841 (17) | 3.4298 (19) | 121.6 (12) |
C6—H6···O1iv | 0.942 (17) | 2.835 (17) | 3.664 (2) | 147.5 (13) |
Symmetry codes: (i) −x+2, −y, −z+2; (ii) x−1, −y+1/2, z−1/2; (iii) −x+1, y+1/2, −z+3/2; (iv) −x+2, y+1/2, −z+3/2. |
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Phthalazines, also called benzo-orthodiazines or benzopyridazines, are a group of heterocyclic compounds isomeric with the cinnolines. The practical interest upon phthalazine derivatives is based on their widespread applications. Phthalazines, like other members of the isomeric diazine series, have found wide applications as therapeutic agents. Phthalazines are also commonly used as ligands in transition metal catalysis, as chemiluminescent materials and for optical applications (Cheng et al., 1999). 2-Substituted-8-(4,6-dimethoxy- pyrimidin-2-yloxy)-4-methylphthalazin-1-one derivatives are used as herbicides. In view of the importance of the title compound, (I), we herein report its crystal structure.
In the molecule of the title compound, (I), (Fig. 1), the bond lengths and angles are within normal ranges (Allen et al., 1987). The rings A (N1/N2/C1/C2/C7/C8) and B (C2—C7) are, of course, planar and they are also coplanar with a dihedral angle of A/B = 0.52 (7)°.
In the crystal structure, intermolecular N—H···O, C—H···N and C—H···O hydrogen bonds (Table 1) link the molecules, in which N—H···O bonds generate the centrosymmetric R22(8) dimers (Etter, 1990), and they are connected by C—H···O and C—H···N bonds to generate the edge-fussed [R32(8) R33(14)] ring motifs (Fig. 2). In addition, the three-dimensional network including these motifs are also linked by π···π interactions, occurring between the Cg1—Cg2 rings (Cg1 and Cg2 are the centroids of rings A and B) of the molecules at (x, y, z) and (x - 1, y, z), with a centroid-to-centroid distance of 3.588 (1) Å and a plane-to-plane separation of 3.434 Å.