organic compounds
5,6-Dipropylphthalazino[2,3-a]cinnoline-8,13-dione
aDepartment of Physics, Presidency College (Autonomous), Chennai 600 005, India, and bOrganic Chemistry, CSIR–Central Leather Research Institute, Adyar, Chennai 600 020, India
*Correspondence e-mail: aspandian59@gmail.com
In the title compound, C22H22N2O2, the two central fused pyridazine rings have screw-boat conformations and the dihedral angle between their mean planes is 36.22 (8)°. The mean plane of the cinnoline ring system makes a dihedral angle of 46.56 (5)° with the mean plane of the phthalazine ring to which it is fused. In the crystal, molecules are linked via C—H⋯O hydrogen bonds, forming chains along the b axis. The chains are reinforced by C—H⋯π interactions.
Keywords: crystal structure; phthalazine derivatives; biological properties; optical properties; C—H⋯O hydrogen bonding; C—H⋯π interactions..
CCDC reference: 1476079
Structure description
Phthalazines, also called benzo-ortho-diazines or benzopyridazines, are a group of isomeric with the cinnolines. The practical interest in phthalazine derivatives is based on their widespread applications (Coates, 1999). Benzopyridazines, like other members of the isomeric diazene series, have found wide applications, including as therapeutic agents, ligands in transition metal catalysis, chemiluminescent and optical materials (Cheng et al., 1999). Phthalazine derivatives have played an important role in the development of corrosion science as they can inhibit the corrosion of mild steel (Musa et al., 2012). Moreover, they are of particular interest owing to their biological activity and optical properties (Caira et al., 2011). Against this background, the of the title compound has been determined and the results are presented herein.
In the title compound, Fig. 1, the two pyridazine rings (C5/C6/C7/N1/N2/C8 and N1/C9/C14–C16/N2) are conjugated and their mean planes are oriented at a dihedral angle of 36.22 (8)°. The phthalazine (N1/N2/C9–C16) unit consists of a benzene ring and a pyridazine ring which is fused with the cinnoline (N1/N2/C1–C8) ring system. The mean plane of the cinnoline ring system is inclined to the mean plane of the phthalazine ring by 46.56 (5)°.
In the crystal, molecules are connected by C—H⋯O hydrogen bonds, leading to chains along the b axis (Table 1 and Fig. 2). In addition, within the chains there are C—H⋯π interactions, involving a benzene ring (C1–C6) H atom and the benzene ring (C9–C14) of an adjacent molecule (Table 1 and Fig. 2).
Synthesis and crystallization
2-Phenyl-2,3-dihydrophthalazine-1,4-dione (0.3 mmol) was treated with oct-4-yne (0.3 mmol) in the presence of [RuCl2(p-cymene)2] (2.5 mol%), Cu(OAc)2·H2O (1 equiv) and AgSbF6 (0.03 mmol) in 1,2-dichloroethane at 273 K for 2.5 h in an open atmosphere. After cooling to ambient temperature, the reaction mixture was diluted with dichloroethane, filtered through Celite and the filtrate was concentrated. The crude residue was purified through a silica gel column using petroleum ether and ethyl acetate as giving the title compound in pure form as block-like orange crystals (yield 90%).
Refinement
Crystal data, data collection and structure .
details are summarized in Table 2Structural data
CCDC reference: 1476079
10.1107/S241431461600688X/su4026sup1.cif
contains datablocks global, I. DOI:Structure factors: contains datablock I. DOI: 10.1107/S241431461600688X/su4026Isup2.hkl
Supporting information file. DOI: 10.1107/S241431461600688X/su4026Isup3.cml
2-Phenyl-2,3-dihydrophthalazine-1, 4-dione (0.3 mmol) was treated with oct-4-yne (0.3 mmol) in the presence of [RuCl2(p-cymene)2] (2.5 mol%), Cu(OAc)2·H2O (1 equiv) and AgSbF6 (0.03 mmol) in 1,2-dichloroethane at 273 K for 2.5 h in an open atmosphere. After cooling to ambient temperature, the reaction mixture was diluted with dichloroethane, filtered through Celite and the filtrate was concentrated. The crude residue was purified through a silica gel column using petroleum ether and ethyl acetate as
giving the title compound in pure form as block-like orange crystals (yield 90%).Phthalazines, also called benzo-ortho-diazines or benzopyridazines, are a group of
isomeric with the cinnolines. The practical interest in phthalazine derivatives is based on their widespread applications (Coates, 1999). Benzopyridazines, like other members of the isomeric diazene series, have found wide applications, including as therapeutic agents, ligands in transition metal catalysis, chemiluminescent and optical materials (Cheng et al., 1999). Phthalazine derivatives have played an important role in the development of corrosion science as they can inhibit the corrosion of mild steel (Musa et al., 2012). Moreover, they are of particular interest owing to their biological activity and optical properties (Caira et al., 2011). Against this background, the of the title compound has been determined and the results are presented herein.In the title compound, Fig. 1, the two pyridazine rings (C5/C6/C7/N1/N2/C8 and N1/C9/C2/C14–C16/N2) are conjugated and their mean planes are oriented at a dihedral angle of 36.22 (8)°. The phthalazine (N1/N2/C9–C16) unit consists of a benzene ring and a pyridazine ring which is fused with the cinnoline (N1/N2/C1–C8) ring system. The mean plane of the cinnoline ring system is inclined to the mean plane of the phthalazine ring by 46.56 (5)°.
In the crystal, molecules are connected by C—H···O hydrogen bonds, leading to chains along the b axis (Table 1 and Fig. 2). In addition, within the chains there are C—H···π interactions, involving a benzene ring (C1–C6) H atom and the benzene ring (C9–C14) of an adjacent molecule (Table 1 and Fig. 2).
Data collection: APEX2 (Bruker, 2004); cell
APEX2 and SAINT (Bruker, 2004); data reduction: SAINT and XPREP (Bruker, 2004); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: PLATON (Spek, 2009) and Mercury (Macrae et al., 2008); software used to prepare material for publication: SHELXL97 (Sheldrick, 2008) and PLATON (Spek, 2009).Fig. 1. The molecular structure of the title compound, with atomic labelling and displacement ellipsoids drawn at the 30% probability level. | |
Fig. 2. A view along the a axis of the crystal packing of the title compound. The hydrogen bonds and C—H···π interactions are shown as dashed lines (see Table 1); C-bound H atoms not involved in these interactions have been omitted for clarity. |
C22H22N2O2 | F(000) = 736 |
Mr = 346.42 | Dx = 1.277 Mg m−3 |
Monoclinic, P21/n | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: -P 2yn | Cell parameters from 2644 reflections |
a = 8.8711 (7) Å | θ = 1.7–25.0° |
b = 8.6175 (6) Å | µ = 0.08 mm−1 |
c = 23.698 (2) Å | T = 293 K |
β = 99.672 (4)° | Block, orange |
V = 1785.9 (2) Å3 | 0.22 × 0.20 × 0.18 mm |
Z = 4 |
Bruker Kappa APEXII CCD diffractometer | 3153 independent reflections |
Radiation source: fine-focus sealed tube | 2644 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.022 |
ω and φ scan | θmax = 25.0°, θmin = 1.7° |
Absorption correction: multi-scan (SADABS; Bruker, 2004) | h = −10→10 |
Tmin = 0.983, Tmax = 0.986 | k = −10→10 |
24172 measured reflections | l = −28→28 |
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)] = 0.043 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.148 | H-atom parameters constrained |
S = 1.08 | w = 1/[σ2(Fo2) + (0.0908P)2 + 0.5529P] where P = (Fo2 + 2Fc2)/3 |
3153 reflections | (Δ/σ)max = 0.003 |
235 parameters | Δρmax = 0.46 e Å−3 |
0 restraints | Δρmin = −0.30 e Å−3 |
C22H22N2O2 | V = 1785.9 (2) Å3 |
Mr = 346.42 | Z = 4 |
Monoclinic, P21/n | Mo Kα radiation |
a = 8.8711 (7) Å | µ = 0.08 mm−1 |
b = 8.6175 (6) Å | T = 293 K |
c = 23.698 (2) Å | 0.22 × 0.20 × 0.18 mm |
β = 99.672 (4)° |
Bruker Kappa APEXII CCD diffractometer | 3153 independent reflections |
Absorption correction: multi-scan (SADABS; Bruker, 2004) | 2644 reflections with I > 2σ(I) |
Tmin = 0.983, Tmax = 0.986 | Rint = 0.022 |
24172 measured reflections |
R[F2 > 2σ(F2)] = 0.043 | 0 restraints |
wR(F2) = 0.148 | H-atom parameters constrained |
S = 1.08 | Δρmax = 0.46 e Å−3 |
3153 reflections | Δρmin = −0.30 e Å−3 |
235 parameters |
Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds 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 > 2sigma(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 | ||
C20 | −0.0632 (2) | 0.3401 (2) | 0.06495 (10) | 0.0484 (5) | |
H20A | −0.1029 | 0.3292 | 0.0244 | 0.058* | |
H20B | −0.1352 | 0.4034 | 0.0814 | 0.058* | |
C17 | 0.0105 (2) | 0.6434 (3) | 0.13449 (9) | 0.0482 (5) | |
H17A | −0.0774 | 0.5785 | 0.1372 | 0.058* | |
H17B | −0.0267 | 0.7388 | 0.1153 | 0.058* | |
C21 | −0.0576 (3) | 0.1802 (3) | 0.09234 (13) | 0.0697 (7) | |
H21A | −0.1598 | 0.1365 | 0.0859 | 0.084* | |
H21B | 0.0067 | 0.1134 | 0.0735 | 0.084* | |
C18 | 0.0925 (3) | 0.6819 (3) | 0.19488 (11) | 0.0718 (8) | |
H18A | 0.1694 | 0.7601 | 0.1920 | 0.086* | |
H18B | 0.0188 | 0.7271 | 0.2160 | 0.086* | |
C19 | 0.1672 (4) | 0.5497 (5) | 0.22811 (11) | 0.0994 (11) | |
H19A | 0.2164 | 0.5854 | 0.2650 | 0.149* | |
H19B | 0.2419 | 0.5047 | 0.2081 | 0.149* | |
H19C | 0.0917 | 0.4731 | 0.2328 | 0.149* | |
C22 | 0.0012 (4) | 0.1802 (4) | 0.15434 (17) | 0.1137 (14) | |
H22A | 0.0027 | 0.0759 | 0.1687 | 0.171* | |
H22B | −0.0638 | 0.2430 | 0.1736 | 0.171* | |
H22C | 0.1031 | 0.2218 | 0.1612 | 0.171* | |
N2 | 0.38243 (15) | 0.52725 (16) | 0.10830 (6) | 0.0355 (4) | |
N1 | 0.25819 (16) | 0.63184 (16) | 0.09974 (6) | 0.0363 (4) | |
O2 | 0.17675 (16) | 0.87531 (16) | 0.07850 (7) | 0.0556 (4) | |
C6 | 0.53518 (19) | 0.7336 (2) | 0.15617 (7) | 0.0361 (4) | |
C15 | 0.08719 (19) | 0.4259 (2) | 0.07134 (7) | 0.0362 (4) | |
C5 | 0.4304 (2) | 0.8411 (2) | 0.12868 (7) | 0.0356 (4) | |
O1 | 0.61735 (15) | 0.47147 (16) | 0.15763 (6) | 0.0540 (4) | |
C7 | 0.5168 (2) | 0.5669 (2) | 0.14328 (8) | 0.0376 (4) | |
C14 | 0.21374 (19) | 0.3577 (2) | 0.04659 (7) | 0.0348 (4) | |
C8 | 0.2802 (2) | 0.7886 (2) | 0.09832 (8) | 0.0376 (4) | |
C9 | 0.36383 (19) | 0.40445 (19) | 0.06747 (7) | 0.0327 (4) | |
C16 | 0.11139 (19) | 0.5610 (2) | 0.09891 (8) | 0.0362 (4) | |
C4 | 0.4611 (2) | 0.9990 (2) | 0.13425 (8) | 0.0453 (5) | |
H4 | 0.3922 | 1.0707 | 0.1153 | 0.054* | |
C1 | 0.6675 (2) | 0.7856 (2) | 0.19067 (9) | 0.0466 (5) | |
H1 | 0.7372 | 0.7146 | 0.2096 | 0.056* | |
C11 | 0.4621 (2) | 0.2265 (2) | 0.00602 (9) | 0.0482 (5) | |
H11 | 0.5446 | 0.1813 | −0.0073 | 0.058* | |
C10 | 0.4873 (2) | 0.3395 (2) | 0.04766 (8) | 0.0414 (4) | |
H10 | 0.5863 | 0.3716 | 0.0622 | 0.050* | |
C13 | 0.1931 (2) | 0.2441 (2) | 0.00413 (8) | 0.0457 (5) | |
H13 | 0.0947 | 0.2111 | −0.0109 | 0.055* | |
C2 | 0.6954 (3) | 0.9419 (3) | 0.19691 (10) | 0.0566 (6) | |
H2 | 0.7831 | 0.9763 | 0.2207 | 0.068* | |
C3 | 0.5940 (3) | 1.0488 (2) | 0.16794 (10) | 0.0550 (6) | |
H3 | 0.6157 | 1.1543 | 0.1713 | 0.066* | |
C12 | 0.3160 (3) | 0.1801 (2) | −0.01595 (9) | 0.0518 (5) | |
H12 | 0.2999 | 0.1050 | −0.0445 | 0.062* |
U11 | U22 | U33 | U12 | U13 | U23 | |
C20 | 0.0313 (10) | 0.0492 (11) | 0.0627 (12) | −0.0042 (8) | 0.0022 (9) | −0.0059 (10) |
C17 | 0.0334 (10) | 0.0559 (12) | 0.0555 (12) | 0.0040 (9) | 0.0084 (8) | −0.0095 (10) |
C21 | 0.0503 (13) | 0.0545 (14) | 0.106 (2) | −0.0102 (11) | 0.0196 (13) | 0.0052 (13) |
C18 | 0.0545 (14) | 0.103 (2) | 0.0605 (14) | −0.0009 (14) | 0.0172 (11) | −0.0256 (14) |
C19 | 0.098 (2) | 0.148 (3) | 0.0507 (15) | 0.014 (2) | 0.0079 (15) | 0.0010 (18) |
C22 | 0.102 (3) | 0.105 (3) | 0.126 (3) | −0.040 (2) | −0.005 (2) | 0.055 (2) |
N2 | 0.0265 (7) | 0.0328 (8) | 0.0456 (8) | 0.0040 (6) | 0.0013 (6) | −0.0037 (6) |
N1 | 0.0262 (7) | 0.0328 (8) | 0.0486 (9) | 0.0039 (6) | 0.0022 (6) | −0.0024 (6) |
O2 | 0.0480 (8) | 0.0413 (8) | 0.0720 (10) | 0.0112 (7) | −0.0056 (7) | 0.0040 (7) |
C6 | 0.0328 (9) | 0.0407 (10) | 0.0353 (9) | −0.0043 (8) | 0.0071 (7) | −0.0014 (7) |
C15 | 0.0288 (9) | 0.0388 (9) | 0.0390 (9) | 0.0011 (7) | 0.0000 (7) | 0.0027 (8) |
C5 | 0.0379 (9) | 0.0362 (9) | 0.0340 (9) | −0.0036 (7) | 0.0099 (7) | −0.0010 (7) |
O1 | 0.0394 (8) | 0.0472 (8) | 0.0683 (10) | 0.0084 (6) | −0.0117 (7) | −0.0016 (7) |
C7 | 0.0314 (9) | 0.0395 (10) | 0.0405 (9) | −0.0004 (8) | 0.0022 (7) | 0.0019 (8) |
C14 | 0.0336 (9) | 0.0330 (9) | 0.0367 (9) | 0.0005 (7) | 0.0024 (7) | 0.0018 (7) |
C8 | 0.0393 (10) | 0.0347 (9) | 0.0384 (9) | 0.0036 (8) | 0.0051 (8) | −0.0005 (7) |
C9 | 0.0332 (9) | 0.0292 (8) | 0.0355 (9) | 0.0016 (7) | 0.0055 (7) | 0.0021 (7) |
C16 | 0.0255 (8) | 0.0401 (10) | 0.0414 (9) | 0.0020 (7) | 0.0007 (7) | −0.0004 (8) |
C4 | 0.0516 (12) | 0.0375 (10) | 0.0483 (11) | −0.0049 (9) | 0.0127 (9) | −0.0009 (9) |
C1 | 0.0385 (10) | 0.0520 (12) | 0.0471 (11) | −0.0068 (9) | 0.0012 (8) | −0.0044 (9) |
C11 | 0.0521 (12) | 0.0479 (11) | 0.0487 (11) | 0.0096 (9) | 0.0200 (9) | −0.0023 (9) |
C10 | 0.0353 (10) | 0.0415 (10) | 0.0483 (10) | 0.0011 (8) | 0.0097 (8) | 0.0021 (8) |
C13 | 0.0454 (11) | 0.0462 (11) | 0.0431 (10) | −0.0038 (9) | 0.0009 (8) | −0.0066 (9) |
C2 | 0.0477 (12) | 0.0609 (14) | 0.0595 (13) | −0.0181 (11) | 0.0042 (10) | −0.0158 (11) |
C3 | 0.0621 (14) | 0.0413 (11) | 0.0635 (13) | −0.0153 (10) | 0.0160 (11) | −0.0099 (10) |
C12 | 0.0628 (14) | 0.0485 (12) | 0.0441 (11) | 0.0022 (10) | 0.0094 (10) | −0.0118 (9) |
C20—C15 | 1.511 (2) | C6—C1 | 1.387 (3) |
C20—C21 | 1.521 (3) | C6—C5 | 1.394 (3) |
C20—H20A | 0.9700 | C6—C7 | 1.473 (3) |
C20—H20B | 0.9700 | C15—C16 | 1.335 (3) |
C17—C16 | 1.506 (3) | C15—C14 | 1.473 (2) |
C17—C18 | 1.529 (3) | C5—C4 | 1.389 (3) |
C17—H17A | 0.9700 | C5—C8 | 1.475 (2) |
C17—H17B | 0.9700 | O1—C7 | 1.219 (2) |
C21—C22 | 1.474 (4) | C14—C13 | 1.393 (3) |
C21—H21A | 0.9700 | C14—C9 | 1.400 (2) |
C21—H21B | 0.9700 | C9—C10 | 1.381 (2) |
C18—C19 | 1.477 (4) | C4—C3 | 1.376 (3) |
C18—H18A | 0.9700 | C4—H4 | 0.9300 |
C18—H18B | 0.9700 | C1—C2 | 1.373 (3) |
C19—H19A | 0.9600 | C1—H1 | 0.9300 |
C19—H19B | 0.9600 | C11—C12 | 1.373 (3) |
C19—H19C | 0.9600 | C11—C10 | 1.378 (3) |
C22—H22A | 0.9600 | C11—H11 | 0.9300 |
C22—H22B | 0.9600 | C10—H10 | 0.9300 |
C22—H22C | 0.9600 | C13—C12 | 1.376 (3) |
N2—C7 | 1.376 (2) | C13—H13 | 0.9300 |
N2—N1 | 1.4118 (19) | C2—C3 | 1.387 (3) |
N2—C9 | 1.425 (2) | C2—H2 | 0.9300 |
N1—C8 | 1.366 (2) | C3—H3 | 0.9300 |
N1—C16 | 1.435 (2) | C12—H12 | 0.9300 |
O2—C8 | 1.215 (2) | ||
C15—C20—C21 | 115.80 (17) | C16—C15—C14 | 118.18 (16) |
C15—C20—H20A | 108.3 | C16—C15—C20 | 122.84 (17) |
C21—C20—H20A | 108.3 | C14—C15—C20 | 118.97 (16) |
C15—C20—H20B | 108.3 | C6—C5—C4 | 120.10 (17) |
C21—C20—H20B | 108.3 | C6—C5—C8 | 120.05 (16) |
H20A—C20—H20B | 107.4 | C4—C5—C8 | 119.58 (17) |
C16—C17—C18 | 113.12 (16) | O1—C7—N2 | 121.35 (16) |
C16—C17—H17A | 109.0 | O1—C7—C6 | 123.36 (16) |
C18—C17—H17A | 109.0 | N2—C7—C6 | 114.95 (15) |
C16—C17—H17B | 109.0 | C13—C14—C9 | 117.34 (17) |
C18—C17—H17B | 109.0 | C13—C14—C15 | 123.45 (16) |
H17A—C17—H17B | 107.8 | C9—C14—C15 | 119.18 (15) |
C22—C21—C20 | 113.9 (2) | O2—C8—N1 | 121.03 (17) |
C22—C21—H21A | 108.8 | O2—C8—C5 | 124.17 (16) |
C20—C21—H21A | 108.8 | N1—C8—C5 | 114.38 (15) |
C22—C21—H21B | 108.8 | C10—C9—C14 | 121.67 (16) |
C20—C21—H21B | 108.8 | C10—C9—N2 | 121.60 (15) |
H21A—C21—H21B | 107.7 | C14—C9—N2 | 116.67 (15) |
C19—C18—C17 | 115.6 (2) | C15—C16—N1 | 116.65 (16) |
C19—C18—H18A | 108.4 | C15—C16—C17 | 128.55 (17) |
C17—C18—H18A | 108.4 | N1—C16—C17 | 114.52 (15) |
C19—C18—H18B | 108.4 | C3—C4—C5 | 119.72 (19) |
C17—C18—H18B | 108.4 | C3—C4—H4 | 120.1 |
H18A—C18—H18B | 107.4 | C5—C4—H4 | 120.1 |
C18—C19—H19A | 109.5 | C2—C1—C6 | 120.0 (2) |
C18—C19—H19B | 109.5 | C2—C1—H1 | 120.0 |
H19A—C19—H19B | 109.5 | C6—C1—H1 | 120.0 |
C18—C19—H19C | 109.5 | C12—C11—C10 | 120.46 (18) |
H19A—C19—H19C | 109.5 | C12—C11—H11 | 119.8 |
H19B—C19—H19C | 109.5 | C10—C11—H11 | 119.8 |
C21—C22—H22A | 109.5 | C11—C10—C9 | 119.16 (18) |
C21—C22—H22B | 109.5 | C11—C10—H10 | 120.4 |
H22A—C22—H22B | 109.5 | C9—C10—H10 | 120.4 |
C21—C22—H22C | 109.5 | C12—C13—C14 | 121.06 (19) |
H22A—C22—H22C | 109.5 | C12—C13—H13 | 119.5 |
H22B—C22—H22C | 109.5 | C14—C13—H13 | 119.5 |
C7—N2—N1 | 120.31 (14) | C1—C2—C3 | 120.5 (2) |
C7—N2—C9 | 125.69 (14) | C1—C2—H2 | 119.7 |
N1—N2—C9 | 112.21 (13) | C3—C2—H2 | 119.7 |
C8—N1—N2 | 121.55 (14) | C4—C3—C2 | 120.10 (19) |
C8—N1—C16 | 123.60 (14) | C4—C3—H3 | 120.0 |
N2—N1—C16 | 114.53 (13) | C2—C3—H3 | 120.0 |
C1—C6—C5 | 119.51 (17) | C11—C12—C13 | 120.29 (18) |
C1—C6—C7 | 119.38 (17) | C11—C12—H12 | 119.9 |
C5—C6—C7 | 120.64 (16) | C13—C12—H12 | 119.9 |
C15—C20—C21—C22 | 58.1 (3) | C13—C14—C9—C10 | −1.0 (3) |
C16—C17—C18—C19 | −53.8 (3) | C15—C14—C9—C10 | 177.11 (16) |
C7—N2—N1—C8 | 34.3 (2) | C13—C14—C9—N2 | 176.26 (16) |
C9—N2—N1—C8 | −131.28 (17) | C15—C14—C9—N2 | −5.6 (2) |
C7—N2—N1—C16 | −139.42 (16) | C7—N2—C9—C10 | −18.3 (3) |
C9—N2—N1—C16 | 54.97 (19) | N1—N2—C9—C10 | 146.39 (16) |
C21—C20—C15—C16 | −118.0 (2) | C7—N2—C9—C14 | 164.43 (16) |
C21—C20—C15—C14 | 61.5 (3) | N1—N2—C9—C14 | −30.9 (2) |
C1—C6—C5—C4 | 2.3 (3) | C14—C15—C16—N1 | 2.7 (2) |
C7—C6—C5—C4 | −169.90 (17) | C20—C15—C16—N1 | −177.77 (16) |
C1—C6—C5—C8 | −171.73 (16) | C14—C15—C16—C17 | −170.79 (17) |
C7—C6—C5—C8 | 16.1 (3) | C20—C15—C16—C17 | 8.7 (3) |
N1—N2—C7—O1 | 169.68 (17) | C8—N1—C16—C15 | 145.59 (18) |
C9—N2—C7—O1 | −26.8 (3) | N2—N1—C16—C15 | −40.8 (2) |
N1—N2—C7—C6 | −16.8 (2) | C8—N1—C16—C17 | −40.0 (2) |
C9—N2—C7—C6 | 146.75 (16) | N2—N1—C16—C17 | 133.61 (16) |
C1—C6—C7—O1 | −6.0 (3) | C18—C17—C16—C15 | 125.2 (2) |
C5—C6—C7—O1 | 166.16 (18) | C18—C17—C16—N1 | −48.4 (2) |
C1—C6—C7—N2 | −179.40 (16) | C6—C5—C4—C3 | −1.3 (3) |
C5—C6—C7—N2 | −7.2 (2) | C8—C5—C4—C3 | 172.72 (17) |
C16—C15—C14—C13 | −161.28 (18) | C5—C6—C1—C2 | −0.9 (3) |
C20—C15—C14—C13 | 19.2 (3) | C7—C6—C1—C2 | 171.37 (19) |
C16—C15—C14—C9 | 20.7 (2) | C12—C11—C10—C9 | 0.7 (3) |
C20—C15—C14—C9 | −158.80 (16) | C14—C9—C10—C11 | 0.4 (3) |
N2—N1—C8—O2 | 163.23 (17) | N2—C9—C10—C11 | −176.71 (16) |
C16—N1—C8—O2 | −23.6 (3) | C9—C14—C13—C12 | 0.5 (3) |
N2—N1—C8—C5 | −23.9 (2) | C15—C14—C13—C12 | −177.50 (18) |
C16—N1—C8—C5 | 149.23 (16) | C6—C1—C2—C3 | −1.4 (3) |
C6—C5—C8—O2 | 171.95 (18) | C5—C4—C3—C2 | −1.0 (3) |
C4—C5—C8—O2 | −2.1 (3) | C1—C2—C3—C4 | 2.4 (3) |
C6—C5—C8—N1 | −0.6 (2) | C10—C11—C12—C13 | −1.1 (3) |
C4—C5—C8—N1 | −174.65 (16) | C14—C13—C12—C11 | 0.5 (3) |
Cg4 is the centroid of the C9–C14 ring. |
D—H···A | D—H | H···A | D···A | D—H···A |
C21—H21B···O2i | 0.97 | 2.54 | 3.400 (3) | 148 |
C4—H4···Cg4ii | 0.93 | 2.83 | 3.633 | 145 |
Symmetry codes: (i) x, y−1, z; (ii) x, y+1, z. |
Cg4 is the centroid of the C9–C14 ring. |
D—H···A | D—H | H···A | D···A | D—H···A |
C21—H21B···O2i | 0.97 | 2.54 | 3.400 (3) | 148 |
C4—H4···Cg4ii | 0.93 | 2.83 | 3.633 | 145 |
Symmetry codes: (i) x, y−1, z; (ii) x, y+1, z. |
Experimental details
Crystal data | |
Chemical formula | C22H22N2O2 |
Mr | 346.42 |
Crystal system, space group | Monoclinic, P21/n |
Temperature (K) | 293 |
a, b, c (Å) | 8.8711 (7), 8.6175 (6), 23.698 (2) |
β (°) | 99.672 (4) |
V (Å3) | 1785.9 (2) |
Z | 4 |
Radiation type | Mo Kα |
µ (mm−1) | 0.08 |
Crystal size (mm) | 0.22 × 0.20 × 0.18 |
Data collection | |
Diffractometer | Bruker Kappa APEXII CCD |
Absorption correction | Multi-scan (SADABS; Bruker, 2004) |
Tmin, Tmax | 0.983, 0.986 |
No. of measured, independent and observed [I > 2σ(I)] reflections | 24172, 3153, 2644 |
Rint | 0.022 |
(sin θ/λ)max (Å−1) | 0.595 |
Refinement | |
R[F2 > 2σ(F2)], wR(F2), S | 0.043, 0.148, 1.08 |
No. of reflections | 3153 |
No. of parameters | 235 |
H-atom treatment | H-atom parameters constrained |
Δρmax, Δρmin (e Å−3) | 0.46, −0.30 |
Computer programs: APEX2 (Bruker, 2004), APEX2 and SAINT (Bruker, 2004), SAINT and XPREP (Bruker, 2004), SHELXS97 (Sheldrick, 2008), PLATON (Spek, 2009) and Mercury (Macrae et al., 2008), SHELXL97 (Sheldrick, 2008) and PLATON (Spek, 2009).
Acknowledgements
The authors thank Dr Babu Varghese, SAIF, IIT, Chennai, India, for the data collection.
References
Bruker (2004). APEX2, SAINT, XPREP and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
Caira, M. R., Georgescu, E., Georgescu, F., Albota, F. & Dumitrascu, F. (2011). Monatsh. Chem. 142, 743–748. CrossRef CAS Google Scholar
Cheng, Y., Ma, B. & Wudl, F. (1999). J. Mater. Chem. 9, 2183–2188. CrossRef CAS Google Scholar
Coates, W. J. (1999). In Comprehensive Heterocyclic Chemistry II . 30, Vol. 6, edited by A. R. Katritzky, C. W. Rees & E. F. V. Scriven. Oxford: Pergamon Press. Google Scholar
Macrae, C. F., Bruno, I. J., Chisholm, J. A., Edgington, P. R., McCabe, P., Pidcock, E., Rodriguez-Monge, L., Taylor, R., van de Streek, J. & Wood, P. A. (2008). J. Appl. Cryst. 41, 466–470. Web of Science CSD CrossRef CAS IUCr Journals Google Scholar
Musa, A. Y., Jalgham, R. T. T. & Mohamad, A. B. (2012). Corros. Sci. 56, 176–183. CrossRef CAS Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar
Spek, A. L. (2009). Acta Cryst. D65, 148–155. Web of Science CrossRef CAS IUCr Journals Google Scholar
This is an open-access article distributed under the terms of the Creative Commons Attribution (CC-BY) Licence, which permits unrestricted use, distribution, and reproduction in any medium, provided the original authors and source are cited.