Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536801002811/ci6008sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S1600536801002811/ci6008Isup2.hkl |
CCDC reference: 159859
Key indicators
- Single-crystal X-ray study
- T = 296 K
- Mean (C-C) = 0.003 Å
- R factor = 0.047
- wR factor = 0.182
- Data-to-parameter ratio = 15.3
checkCIF results
No syntax errors found ADDSYM reports no extra symmetry
Alert Level C:
REFLT_03 From the CIF: _diffrn_reflns_theta_max 77.31 From the CIF: _reflns_number_total 4847 TEST2: Reflns within _diffrn_reflns_theta_max Count of symmetry unique reflns 5333 Completeness (_total/calc) 90.89% Alert C: < 95% complete
0 Alert Level A = Potentially serious problem
0 Alert Level B = Potential problem
1 Alert Level C = Please check
A mixture of 2-{[N-benzyl-N-(prop-2'-ynyl)]amino}benzamide, p-methoxyiodobenzene, (Ph3P)2PdCl2, CuI and triethylamine in acetonitrile was stirred for about 16 h at room temperature. After usual work-up, the product was purified by column chromatography on silica gel (60–120 mesh) to yield a disubstituted alkyne which was then refluxed with NaOEt in ethanol for about 48 h. The crude product on chromatography through silica gel yielded the title compound, (I), on elution with CHCl3. The m.p. of the title compound is 458 K. Single crystals suitable for X-ray analysis were obtained by slow crystallization from a dilute solution of (I) in a light petroleum (333–353 K)—chloroform mixture (3:1).
H atoms were refined using a riding model and their isotropic displacement parameters were set to 1.2 times (1.5 times for CH3 groups) the equivalent displacement parameters of their parent atoms.
Data collection: MSC/AFC Diffractometer Control Software (Molecular Structure Corporation, 1994); cell refinement: MSC/AFC Diffractometer Control Software; data reduction: TEXSAN (Molecular Structure Corporation, 1995); program(s) used to solve structure: MULTAN88 (Debaerdemaeker et al., 1988); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ZORTEP (Zsolnai, 1995); software used to prepare material for publication: SHELXL97.
C31H28N2O2 | F(000) = 976 |
Mr = 460.55 | Dx = 1.219 Mg m−3 |
Monoclinic, P21/c | Cu Kα radiation, λ = 1.54180 Å |
a = 13.281 (3) Å | Cell parameters from 21 reflections |
b = 11.161 (2) Å | θ = 38.7–39.8° |
c = 17.756 (3) Å | µ = 0.60 mm−1 |
β = 107.49 (1)° | T = 296 K |
V = 2510.3 (8) Å3 | Prismatic, colourless |
Z = 4 | 0.50 × 0.37 × 0.25 mm |
Rigaku AFC-5R diffractometer | 3442 reflections with I > 2σ(I) |
Radiation source: Rigaku rotating anode | Rint = 0.017 |
Graphite monochromator | θmax = 77.3°, θmin = 5.2° |
ω–2θ scans | h = −16→16 |
Absorption correction: empirical (using intensity measurements) (North et al., 1968) | k = 0→14 |
Tmin = 0.754, Tmax = 0.865 | l = 0→21 |
5062 measured reflections | 3 standard reflections every 150 reflections |
4847 independent reflections | intensity decay: 0.1% |
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)] = 0.047 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.182 | H-atom parameters constrained |
S = 1.04 | w = 1/[σ2(Fo2) + (0.12P)2] where P = (Fo2 + 2Fc2)/3 |
4847 reflections | (Δ/σ)max = 0.001 |
316 parameters | Δρmax = 0.16 e Å−3 |
0 restraints | Δρmin = −0.17 e Å−3 |
C31H28N2O2 | V = 2510.3 (8) Å3 |
Mr = 460.55 | Z = 4 |
Monoclinic, P21/c | Cu Kα radiation |
a = 13.281 (3) Å | µ = 0.60 mm−1 |
b = 11.161 (2) Å | T = 296 K |
c = 17.756 (3) Å | 0.50 × 0.37 × 0.25 mm |
β = 107.49 (1)° |
Rigaku AFC-5R diffractometer | 3442 reflections with I > 2σ(I) |
Absorption correction: empirical (using intensity measurements) (North et al., 1968) | Rint = 0.017 |
Tmin = 0.754, Tmax = 0.865 | 3 standard reflections every 150 reflections |
5062 measured reflections | intensity decay: 0.1% |
4847 independent reflections |
R[F2 > 2σ(F2)] = 0.047 | 0 restraints |
wR(F2) = 0.182 | H-atom parameters constrained |
S = 1.04 | Δρmax = 0.16 e Å−3 |
4847 reflections | Δρmin = −0.17 e Å−3 |
316 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 | ||
O1 | 0.12109 (13) | 0.26532 (14) | 0.50919 (10) | 0.0753 (5) | |
O2 | 0.82452 (12) | 0.16910 (15) | 0.91234 (9) | 0.0713 (5) | |
N1 | 0.29782 (12) | −0.03000 (13) | 0.50837 (9) | 0.0483 (4) | |
N2 | 0.19022 (12) | 0.08853 (14) | 0.56555 (10) | 0.0497 (4) | |
C1 | 0.25243 (15) | 0.17204 (16) | 0.46290 (11) | 0.0480 (5) | |
C2 | 0.25862 (18) | 0.26728 (18) | 0.41360 (13) | 0.0596 (5) | |
H2 | 0.2263 | 0.3397 | 0.4180 | 0.071* | |
C3 | 0.31168 (19) | 0.2556 (2) | 0.35874 (14) | 0.0637 (6) | |
H3 | 0.3172 | 0.3204 | 0.3273 | 0.076* | |
C4 | 0.35685 (18) | 0.1473 (2) | 0.35048 (13) | 0.0624 (6) | |
H4 | 0.3904 | 0.1387 | 0.3117 | 0.075* | |
C5 | 0.35337 (16) | 0.05100 (18) | 0.39870 (12) | 0.0549 (5) | |
H5 | 0.3843 | −0.0215 | 0.3923 | 0.066* | |
C6 | 0.30320 (14) | 0.06310 (15) | 0.45713 (11) | 0.0457 (4) | |
C7 | 0.36713 (16) | −0.13447 (17) | 0.51518 (12) | 0.0533 (5) | |
H7A | 0.3781 | −0.1705 | 0.5668 | 0.064* | |
H7B | 0.4352 | −0.1073 | 0.5123 | 0.064* | |
C8 | 0.32573 (15) | −0.22976 (16) | 0.45266 (11) | 0.0475 (4) | |
C9 | 0.22618 (17) | −0.22583 (18) | 0.39858 (13) | 0.0600 (6) | |
H9 | 0.1818 | −0.1615 | 0.3989 | 0.072* | |
C10 | 0.1919 (2) | −0.31680 (19) | 0.34394 (14) | 0.0669 (6) | |
H10 | 0.1250 | −0.3126 | 0.3074 | 0.080* | |
C11 | 0.2558 (2) | −0.41318 (19) | 0.34320 (15) | 0.0680 (6) | |
H11 | 0.2325 | −0.4744 | 0.3066 | 0.082* | |
C12 | 0.3543 (2) | −0.41813 (18) | 0.39692 (16) | 0.0705 (7) | |
H12 | 0.3978 | −0.4836 | 0.3971 | 0.085* | |
C13 | 0.38974 (18) | −0.32694 (18) | 0.45081 (14) | 0.0606 (6) | |
H13 | 0.4573 | −0.3308 | 0.4863 | 0.073* | |
C14 | 0.18352 (16) | 0.18271 (17) | 0.51486 (12) | 0.0523 (5) | |
C15 | 0.28152 (15) | 0.00677 (17) | 0.58257 (11) | 0.0482 (4) | |
H15 | 0.2647 | −0.0648 | 0.6084 | 0.058* | |
C16 | 0.37966 (15) | 0.06381 (17) | 0.63793 (11) | 0.0507 (5) | |
H16 | 0.4042 | 0.1348 | 0.6222 | 0.061* | |
C17 | 0.43255 (16) | 0.01784 (18) | 0.70769 (12) | 0.0516 (5) | |
H17 | 0.4025 | −0.0489 | 0.7238 | 0.062* | |
C18 | 0.53258 (15) | 0.05978 (17) | 0.76225 (11) | 0.0494 (5) | |
C19 | 0.58301 (17) | −0.0079 (2) | 0.82877 (12) | 0.0582 (5) | |
H19 | 0.5502 | −0.0769 | 0.8391 | 0.070* | |
C20 | 0.68051 (16) | 0.0240 (2) | 0.88023 (12) | 0.0586 (5) | |
H20 | 0.7125 | −0.0236 | 0.9239 | 0.070* | |
C21 | 0.72952 (15) | 0.12667 (18) | 0.86599 (12) | 0.0523 (5) | |
C22 | 0.88368 (19) | 0.0943 (3) | 0.97552 (16) | 0.0817 (8) | |
H22A | 0.9481 | 0.1340 | 1.0037 | 0.123* | |
H22B | 0.8997 | 0.0200 | 0.9545 | 0.123* | |
H22C | 0.8429 | 0.0788 | 1.0109 | 0.123* | |
C23 | 0.68120 (17) | 0.19522 (18) | 0.79974 (13) | 0.0566 (5) | |
H23 | 0.7143 | 0.2642 | 0.7897 | 0.068* | |
C24 | 0.58526 (18) | 0.16254 (17) | 0.74882 (12) | 0.0552 (5) | |
H24 | 0.5546 | 0.2095 | 0.7046 | 0.066* | |
C25 | 0.12296 (15) | 0.07730 (18) | 0.61525 (11) | 0.0504 (5) | |
C26 | 0.06239 (16) | −0.0250 (2) | 0.60991 (12) | 0.0592 (5) | |
H26 | 0.0631 | −0.0834 | 0.5728 | 0.071* | |
C27 | 0.00093 (18) | −0.0405 (2) | 0.65954 (14) | 0.0674 (6) | |
H27 | −0.0395 | −0.1097 | 0.6551 | 0.081* | |
C28 | −0.00192 (18) | 0.0443 (2) | 0.71584 (15) | 0.0696 (6) | |
C29 | −0.0680 (3) | 0.0265 (3) | 0.7711 (2) | 0.1057 (11) | |
H29A | −0.0599 | 0.0944 | 0.8056 | 0.158* | |
H29B | −0.0452 | −0.0446 | 0.8020 | 0.158* | |
H29C | −0.1409 | 0.0183 | 0.7409 | 0.158* | |
C30 | 0.0585 (2) | 0.1466 (2) | 0.71953 (15) | 0.0724 (7) | |
H30 | 0.0574 | 0.2053 | 0.7564 | 0.087* | |
C31 | 0.12039 (18) | 0.1644 (2) | 0.67012 (13) | 0.0616 (6) | |
H31 | 0.1598 | 0.2342 | 0.6738 | 0.074* |
U11 | U22 | U33 | U12 | U13 | U23 | |
O1 | 0.0824 (11) | 0.0629 (9) | 0.0877 (11) | 0.0357 (8) | 0.0363 (9) | 0.0164 (8) |
O2 | 0.0550 (9) | 0.0756 (11) | 0.0729 (10) | −0.0124 (7) | 0.0033 (8) | −0.0016 (8) |
N1 | 0.0517 (9) | 0.0403 (8) | 0.0484 (9) | 0.0090 (7) | 0.0083 (7) | −0.0020 (7) |
N2 | 0.0474 (8) | 0.0473 (9) | 0.0528 (9) | 0.0098 (7) | 0.0126 (7) | 0.0009 (7) |
C1 | 0.0467 (10) | 0.0426 (9) | 0.0497 (10) | 0.0052 (8) | 0.0066 (8) | −0.0021 (8) |
C2 | 0.0704 (13) | 0.0427 (10) | 0.0639 (13) | 0.0086 (9) | 0.0176 (11) | 0.0037 (9) |
C3 | 0.0784 (15) | 0.0508 (11) | 0.0639 (13) | 0.0023 (10) | 0.0242 (12) | 0.0069 (10) |
C4 | 0.0696 (14) | 0.0637 (13) | 0.0577 (12) | 0.0016 (11) | 0.0248 (11) | −0.0011 (10) |
C5 | 0.0578 (12) | 0.0492 (10) | 0.0574 (12) | 0.0063 (9) | 0.0167 (10) | −0.0052 (9) |
C6 | 0.0433 (9) | 0.0397 (9) | 0.0476 (10) | 0.0009 (7) | 0.0037 (8) | −0.0037 (7) |
C7 | 0.0513 (11) | 0.0445 (10) | 0.0573 (11) | 0.0115 (8) | 0.0060 (9) | −0.0027 (8) |
C8 | 0.0550 (10) | 0.0370 (9) | 0.0515 (10) | 0.0043 (8) | 0.0177 (9) | 0.0031 (8) |
C9 | 0.0591 (12) | 0.0476 (11) | 0.0663 (13) | 0.0056 (9) | 0.0083 (10) | −0.0064 (9) |
C10 | 0.0708 (14) | 0.0550 (12) | 0.0669 (14) | −0.0049 (11) | 0.0086 (11) | −0.0084 (10) |
C11 | 0.0864 (17) | 0.0479 (11) | 0.0726 (15) | −0.0087 (11) | 0.0285 (13) | −0.0115 (10) |
C12 | 0.0865 (17) | 0.0405 (10) | 0.0924 (18) | 0.0092 (11) | 0.0389 (15) | −0.0069 (10) |
C13 | 0.0594 (12) | 0.0487 (11) | 0.0732 (14) | 0.0095 (9) | 0.0189 (11) | 0.0018 (10) |
C14 | 0.0524 (10) | 0.0440 (10) | 0.0565 (11) | 0.0080 (8) | 0.0102 (9) | 0.0007 (8) |
C15 | 0.0467 (10) | 0.0431 (9) | 0.0498 (10) | 0.0067 (8) | 0.0068 (8) | 0.0002 (8) |
C16 | 0.0510 (10) | 0.0461 (10) | 0.0502 (11) | 0.0040 (8) | 0.0079 (9) | −0.0035 (8) |
C17 | 0.0518 (10) | 0.0502 (10) | 0.0494 (10) | 0.0008 (9) | 0.0103 (9) | 0.0002 (8) |
C18 | 0.0525 (10) | 0.0488 (10) | 0.0433 (10) | 0.0037 (8) | 0.0093 (8) | −0.0032 (8) |
C19 | 0.0581 (12) | 0.0584 (12) | 0.0531 (12) | −0.0083 (10) | 0.0091 (9) | 0.0084 (9) |
C20 | 0.0545 (11) | 0.0650 (13) | 0.0480 (11) | −0.0029 (10) | 0.0028 (9) | 0.0094 (9) |
C21 | 0.0485 (10) | 0.0542 (11) | 0.0525 (11) | −0.0008 (9) | 0.0124 (9) | −0.0060 (9) |
C22 | 0.0522 (13) | 0.0937 (19) | 0.0801 (17) | −0.0012 (13) | −0.0089 (12) | 0.0036 (14) |
C23 | 0.0627 (12) | 0.0467 (10) | 0.0596 (12) | −0.0051 (9) | 0.0174 (10) | −0.0002 (9) |
C24 | 0.0664 (12) | 0.0446 (10) | 0.0486 (10) | 0.0022 (9) | 0.0085 (9) | 0.0022 (8) |
C25 | 0.0449 (10) | 0.0538 (11) | 0.0483 (10) | 0.0071 (8) | 0.0078 (8) | −0.0002 (8) |
C26 | 0.0585 (12) | 0.0599 (12) | 0.0551 (12) | −0.0036 (10) | 0.0110 (10) | −0.0042 (10) |
C27 | 0.0541 (12) | 0.0760 (15) | 0.0683 (14) | −0.0027 (11) | 0.0128 (11) | 0.0106 (12) |
C28 | 0.0559 (12) | 0.0871 (17) | 0.0672 (14) | 0.0208 (12) | 0.0207 (11) | 0.0170 (13) |
C29 | 0.101 (2) | 0.129 (3) | 0.107 (2) | 0.033 (2) | 0.061 (2) | 0.032 (2) |
C30 | 0.0777 (16) | 0.0782 (16) | 0.0638 (14) | 0.0210 (14) | 0.0249 (12) | −0.0077 (12) |
C31 | 0.0596 (12) | 0.0595 (12) | 0.0638 (13) | 0.0075 (10) | 0.0156 (11) | −0.0089 (10) |
O1—C14 | 1.224 (2) | C15—C16 | 1.517 (3) |
O2—C21 | 1.367 (2) | C15—H15 | 0.9800 |
O2—C22 | 1.429 (3) | C16—C17 | 1.330 (3) |
N1—C6 | 1.397 (2) | C16—H16 | 0.9300 |
N1—C15 | 1.457 (3) | C17—C18 | 1.466 (3) |
N1—C7 | 1.468 (2) | C17—H17 | 0.9300 |
N2—C14 | 1.369 (2) | C18—C19 | 1.392 (3) |
N2—C25 | 1.437 (3) | C18—C24 | 1.401 (3) |
N2—C15 | 1.475 (2) | C19—C20 | 1.388 (3) |
C1—C2 | 1.395 (3) | C19—H19 | 0.9300 |
C1—C6 | 1.409 (2) | C20—C21 | 1.379 (3) |
C1—C14 | 1.487 (3) | C20—H20 | 0.9300 |
C2—C3 | 1.369 (3) | C21—C23 | 1.388 (3) |
C2—H2 | 0.9300 | C22—H22A | 0.9600 |
C3—C4 | 1.377 (3) | C22—H22B | 0.9600 |
C3—H3 | 0.9300 | C22—H22C | 0.9600 |
C4—C5 | 1.384 (3) | C23—C24 | 1.372 (3) |
C4—H4 | 0.9300 | C23—H23 | 0.9300 |
C5—C6 | 1.398 (3) | C24—H24 | 0.9300 |
C5—H5 | 0.9300 | C25—C26 | 1.383 (3) |
C7—C8 | 1.516 (3) | C25—C31 | 1.384 (3) |
C7—H7A | 0.9700 | C26—C27 | 1.380 (3) |
C7—H7B | 0.9700 | C26—H26 | 0.9300 |
C8—C9 | 1.382 (3) | C27—C28 | 1.386 (4) |
C8—C13 | 1.385 (3) | C27—H27 | 0.9300 |
C9—C10 | 1.383 (3) | C28—C30 | 1.385 (4) |
C9—H9 | 0.9300 | C28—C29 | 1.514 (4) |
C10—C11 | 1.373 (3) | C29—H29A | 0.9600 |
C10—H10 | 0.9300 | C29—H29B | 0.9600 |
C11—C12 | 1.369 (3) | C29—H29C | 0.9600 |
C11—H11 | 0.9300 | C30—C31 | 1.385 (3) |
C12—C13 | 1.379 (3) | C30—H30 | 0.9300 |
C12—H12 | 0.9300 | C31—H31 | 0.9300 |
C13—H13 | 0.9300 | ||
C21—O2—C22 | 117.41 (18) | N2—C15—H15 | 108.1 |
C6—N1—C15 | 115.5 (2) | C16—C15—H15 | 108.1 |
C6—N1—C7 | 119.4 (2) | C17—C16—C15 | 123.5 (2) |
C15—N1—C7 | 114.2 (1) | C17—C16—H16 | 118.2 |
C14—N2—C25 | 122.8 (2) | C15—C16—H16 | 118.2 |
C14—N2—C15 | 119.8 (2) | C16—C17—C18 | 127.8 (2) |
C25—N2—C15 | 116.4 (2) | C16—C17—H17 | 116.1 |
C2—C1—C6 | 119.47 (19) | C18—C17—H17 | 116.1 |
C2—C1—C14 | 119.45 (17) | C19—C18—C24 | 116.81 (18) |
C6—C1—C14 | 120.78 (17) | C19—C18—C17 | 119.78 (18) |
C3—C2—C1 | 120.93 (19) | C24—C18—C17 | 123.29 (18) |
C3—C2—H2 | 119.5 | C18—C19—C20 | 122.4 (2) |
C1—C2—H2 | 119.5 | C18—C19—H19 | 118.8 |
C2—C3—C4 | 119.5 (2) | C20—C19—H19 | 118.8 |
C2—C3—H3 | 120.2 | C21—C20—C19 | 119.39 (19) |
C4—C3—H3 | 120.2 | C21—C20—H20 | 120.3 |
C3—C4—C5 | 121.3 (2) | C19—C20—H20 | 120.3 |
C3—C4—H4 | 119.4 | O2—C21—C23 | 115.3 (2) |
C5—C4—H4 | 119.4 | O2—C21—C20 | 125.4 (2) |
C4—C5—C6 | 119.75 (19) | C23—C21—C20 | 119.35 (19) |
C4—C5—H5 | 120.1 | O2—C22—H22A | 109.5 |
C6—C5—H5 | 120.1 | O2—C22—H22B | 109.5 |
C5—C6—N1 | 122.72 (16) | H22A—C22—H22B | 109.5 |
C5—C6—C1 | 118.87 (17) | O2—C22—H22C | 109.5 |
N1—C6—C1 | 118.37 (18) | H22A—C22—H22C | 109.5 |
N1—C7—C8 | 114.61 (15) | H22B—C22—H22C | 109.5 |
N1—C7—H7A | 108.6 | C24—C23—C21 | 120.88 (19) |
C8—C7—H7A | 108.6 | C24—C23—H23 | 119.6 |
N1—C7—H7B | 108.6 | C21—C23—H23 | 119.6 |
C8—C7—H7B | 108.6 | C23—C24—C18 | 121.20 (19) |
H7A—C7—H7B | 107.6 | C23—C24—H24 | 119.4 |
C9—C8—C13 | 118.33 (19) | C18—C24—H24 | 119.4 |
C9—C8—C7 | 123.18 (17) | C26—C25—C31 | 119.4 (2) |
C13—C8—C7 | 118.47 (18) | C26—C25—N2 | 119.07 (18) |
C8—C9—C10 | 120.6 (2) | C31—C25—N2 | 121.48 (19) |
C8—C9—H9 | 119.7 | C25—C26—C27 | 120.2 (2) |
C10—C9—H9 | 119.7 | C25—C26—H26 | 119.9 |
C11—C10—C9 | 120.5 (2) | C27—C26—H26 | 119.9 |
C11—C10—H10 | 119.8 | C26—C27—C28 | 121.6 (2) |
C9—C10—H10 | 119.8 | C26—C27—H27 | 119.2 |
C10—C11—C12 | 119.3 (2) | C28—C27—H27 | 119.2 |
C10—C11—H11 | 120.4 | C27—C28—C30 | 117.2 (2) |
C12—C11—H11 | 120.4 | C27—C28—C29 | 121.6 (3) |
C11—C12—C13 | 120.6 (2) | C30—C28—C29 | 121.2 (3) |
C11—C12—H12 | 119.7 | C28—C29—H29A | 109.5 |
C13—C12—H12 | 119.7 | C28—C29—H29B | 109.5 |
C12—C13—C8 | 120.7 (2) | H29A—C29—H29B | 109.5 |
C12—C13—H13 | 119.6 | C28—C29—H29C | 109.5 |
C8—C13—H13 | 119.6 | H29A—C29—H29C | 109.5 |
O1—C14—N2 | 122.7 (2) | H29B—C29—H29C | 109.5 |
O1—C14—C1 | 122.52 (18) | C31—C30—C28 | 122.3 (2) |
N2—C14—C1 | 114.58 (16) | C31—C30—H30 | 118.9 |
N1—C15—N2 | 109.00 (14) | C28—C30—H30 | 118.9 |
N1—C15—C16 | 111.84 (15) | C25—C31—C30 | 119.3 (2) |
N2—C15—C16 | 111.51 (15) | C25—C31—H31 | 120.3 |
N1—C15—H15 | 108.1 | C30—C31—H31 | 120.3 |
C6—C1—C2—C3 | 1.2 (3) | C6—N1—C15—C16 | −72.47 (19) |
C14—C1—C2—C3 | −172.6 (2) | C7—N1—C15—C16 | 71.6 (2) |
C1—C2—C3—C4 | 2.0 (3) | C14—N2—C15—N1 | −48.7 (2) |
C2—C3—C4—C5 | −2.6 (4) | C25—N2—C15—N1 | 142.79 (16) |
C3—C4—C5—C6 | 0.0 (3) | C14—N2—C15—C16 | 75.3 (2) |
C4—C5—C6—N1 | −179.26 (18) | C25—N2—C15—C16 | −93.25 (19) |
C4—C5—C6—C1 | 3.2 (3) | N1—C15—C16—C17 | −116.7 (2) |
C15—N1—C6—C5 | 157.05 (17) | N2—C15—C16—C17 | 121.0 (2) |
C7—N1—C6—C5 | 15.0 (3) | C15—C16—C17—C18 | 174.27 (18) |
C15—N1—C6—C1 | −25.4 (2) | C16—C17—C18—C19 | −172.4 (2) |
C7—N1—C6—C1 | −167.44 (16) | C16—C17—C18—C24 | 3.4 (3) |
C2—C1—C6—C5 | −3.8 (3) | C24—C18—C19—C20 | 0.4 (3) |
C14—C1—C6—C5 | 169.95 (17) | C17—C18—C19—C20 | 176.5 (2) |
C2—C1—C6—N1 | 178.58 (17) | C18—C19—C20—C21 | 0.6 (3) |
C14—C1—C6—N1 | −7.7 (3) | C22—O2—C21—C23 | −172.3 (2) |
C6—N1—C7—C8 | −84.1 (2) | C22—O2—C21—C20 | 7.6 (3) |
C15—N1—C7—C8 | 133.36 (18) | C19—C20—C21—O2 | 179.0 (2) |
N1—C7—C8—C9 | −6.6 (3) | C19—C20—C21—C23 | −1.0 (3) |
N1—C7—C8—C13 | 174.96 (18) | O2—C21—C23—C24 | −179.57 (19) |
C13—C8—C9—C10 | −0.2 (3) | C20—C21—C23—C24 | 0.5 (3) |
C7—C8—C9—C10 | −178.6 (2) | C21—C23—C24—C18 | 0.5 (3) |
C8—C9—C10—C11 | 0.8 (4) | C19—C18—C24—C23 | −0.9 (3) |
C9—C10—C11—C12 | −0.3 (4) | C17—C18—C24—C23 | −176.9 (2) |
C10—C11—C12—C13 | −0.6 (4) | C14—N2—C25—C26 | 123.3 (2) |
C11—C12—C13—C8 | 1.2 (4) | C15—N2—C25—C26 | −68.5 (2) |
C9—C8—C13—C12 | −0.8 (3) | C14—N2—C25—C31 | −59.0 (3) |
C7—C8—C13—C12 | 177.7 (2) | C15—N2—C25—C31 | 109.2 (2) |
C25—N2—C14—O1 | 1.4 (3) | C31—C25—C26—C27 | −0.8 (3) |
C15—N2—C14—O1 | −166.44 (19) | N2—C25—C26—C27 | 176.94 (18) |
C25—N2—C14—C1 | −174.22 (17) | C25—C26—C27—C28 | −0.2 (3) |
C15—N2—C14—C1 | 18.0 (2) | C26—C27—C28—C30 | 0.9 (3) |
C2—C1—C14—O1 | 9.7 (3) | C26—C27—C28—C29 | −179.1 (2) |
C6—C1—C14—O1 | −164.0 (2) | C27—C28—C30—C31 | −0.6 (4) |
C2—C1—C14—N2 | −174.68 (18) | C29—C28—C30—C31 | 179.3 (2) |
C6—C1—C14—N2 | 11.6 (3) | C26—C25—C31—C30 | 1.0 (3) |
C6—N1—C15—N2 | 51.3 (2) | N2—C25—C31—C30 | −176.62 (19) |
C7—N1—C15—N2 | −164.66 (15) | C28—C30—C31—C25 | −0.3 (4) |
D—H···A | D—H | H···A | D···A | D—H···A |
C22—H22A···O1i | 0.96 | 2.53 | 3.409 (3) | 152 |
Symmetry code: (i) x+1, −y+1/2, z+1/2. |
Experimental details
Crystal data | |
Chemical formula | C31H28N2O2 |
Mr | 460.55 |
Crystal system, space group | Monoclinic, P21/c |
Temperature (K) | 296 |
a, b, c (Å) | 13.281 (3), 11.161 (2), 17.756 (3) |
β (°) | 107.49 (1) |
V (Å3) | 2510.3 (8) |
Z | 4 |
Radiation type | Cu Kα |
µ (mm−1) | 0.60 |
Crystal size (mm) | 0.50 × 0.37 × 0.25 |
Data collection | |
Diffractometer | Rigaku AFC-5R diffractometer |
Absorption correction | Empirical (using intensity measurements) (North et al., 1968) |
Tmin, Tmax | 0.754, 0.865 |
No. of measured, independent and observed [I > 2σ(I)] reflections | 5062, 4847, 3442 |
Rint | 0.017 |
(sin θ/λ)max (Å−1) | 0.633 |
Refinement | |
R[F2 > 2σ(F2)], wR(F2), S | 0.047, 0.182, 1.04 |
No. of reflections | 4847 |
No. of parameters | 316 |
H-atom treatment | H-atom parameters constrained |
Δρmax, Δρmin (e Å−3) | 0.16, −0.17 |
Computer programs: MSC/AFC Diffractometer Control Software (Molecular Structure Corporation, 1994), MSC/AFC Diffractometer Control Software, TEXSAN (Molecular Structure Corporation, 1995), MULTAN88 (Debaerdemaeker et al., 1988), SHELXL97 (Sheldrick, 1997), ZORTEP (Zsolnai, 1995), SHELXL97.
O1—C14 | 1.224 (2) | N2—C14 | 1.369 (2) |
O2—C21 | 1.367 (2) | N2—C25 | 1.437 (3) |
O2—C22 | 1.429 (3) | N2—C15 | 1.475 (2) |
N1—C6 | 1.397 (2) | C15—C16 | 1.517 (3) |
N1—C15 | 1.457 (3) | C16—C17 | 1.330 (3) |
N1—C7 | 1.468 (2) | C17—C18 | 1.466 (3) |
C6—N1—C15 | 115.5 (2) | C25—N2—C15 | 116.4 (2) |
C6—N1—C7 | 119.4 (2) | C17—C16—C15 | 123.5 (2) |
C15—N1—C7 | 114.2 (1) | C16—C17—C18 | 127.8 (2) |
C14—N2—C25 | 122.8 (2) | O2—C21—C23 | 115.3 (2) |
C14—N2—C15 | 119.8 (2) | O2—C21—C20 | 125.4 (2) |
C6—N1—C7—C8 | −84.1 (2) | C14—N2—C25—C31 | −59.0 (3) |
N1—C7—C8—C9 | −6.6 (3) |
D—H···A | D—H | H···A | D···A | D—H···A |
C22—H22A···O1i | 0.96 | 2.53 | 3.409 (3) | 152 |
Symmetry code: (i) x+1, −y+1/2, z+1/2. |
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Substituted quinazolines display therapeutic activity and specific inhibitory effects on tyrosin kinase and dihydrofolate reductase (Jackman et al., 1997; Bridges et al., 1996; Rewcastle et al., 1995). As part of our ongoing studies on the synthesis and characterization of new nitrogen-containing heterocyclic systems of biological importance (Maiti et al., 2000; Mukherjee et al., 1999) and to build up a hierarchy for such systems, the structure determination of 1-benzyl-2-[(p-methoxy)styryl]-3-(p-tolyl)-1,2,3,4-tetrahydroquinazoline-4-one, (I), was undertaken.
In (I), the vinyl C═C bond is in the E configuration [C15—C16—C17—C18 174.3 (2)°]. The six-membered heterocyclic ring (C1/C6/N1/C15/N2/C14) adopts a distorted sofa conformation with C15 deviating by -0.609 (2) Å from the least-squares plane (r.m.s deviation 0.038 Å) defined by the remaining endocyclic atoms. The benzyl and (p-methoxy)styryl substituents are nearly perpendicular to the planar part of quinazoline moiety with dihedral angles of 83.03 (4) and 83.14 (3)°, respectively. The p-tolyl group is oriented at an angle of 46.64 (6)°. The sum of the bond angles around N1 [349.1 (2)°] indicates a pyramidal configuration for it, whereas, N2 [359.0 (2)°] is in the planar trigonal geometry. The bond lengths and angles in (I) are similar to those reported for substituted quinazoline structures (Kubicki et al., 1997; Lindeman et al., 1995). The cis orientation of C22—O2 with respect to C20—C21 about the O2—C21 bond [C22—O2—C21—C20 7.6 (3)°] results in repulsion between C20 and C22 and this caused the widening of C20—C21—O2 and narrowing of C23—C21—O2 from 120°. Similar observation has been reported for heterocyclic compounds with methoxy phenyl substitutions (Mukherjee et al., 2000).
The lack of π bonding in the branches among the phenyl rings precludes any possible π conjugation across the whole molecule. The aromatic nature of the rings is therefore localized within the rings and on their direct substitutions. Except for a weak C—H···O intermolecular interaction involving the carbonyl O atom (Table 1) the crystal packing is essentially stabilized by the van der Waals' forces.