organic compounds
In the title molecule, C22H18N4O, all of the rings and the indole system are individually planar. In the crystal structure, molecules are linked by intermolecular N—HO hydrogen bonds, forming infinite chains running along the [001] direction.
Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536806028133/bh2035sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S1600536806028133/bh2035Isup2.hkl |
CCDC reference: 618778
Computing details top
Data collection: CrystalClear (Rigaku/MSC, 2005); cell refinement: CrystalClear; data reduction: CrystalClear; 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).
N-{4-[(2-Phenyl-1H-indol-3-yl)diazenyl]phenyl}acetamide top
Crystal data top
C22H18N4O | Dx = 1.293 Mg m−3 |
Mr = 354.41 | Melting point = 452–455 K |
Orthorhombic, P212121 | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: P 2ac 2ab | Cell parameters from 7269 reflections |
a = 5.996 (5) Å | θ = 2.4–30.5° |
b = 14.786 (5) Å | µ = 0.08 mm−1 |
c = 20.531 (5) Å | T = 296 K |
V = 1820.2 (17) Å3 | Block, red |
Z = 4 | 0.35 × 0.25 × 0.15 mm |
F(000) = 744 |
Data collection top
Rigaku R-AXIS RAPID-S diffractometer | 1973 reflections with I > 2σ(I) |
Radiation source: fine-focus sealed tube | Rint = 0.094 |
Graphite monochromator | θmax = 30.6°, θmin = 2.4° |
ω scans | h = −7→8 |
52939 measured reflections | k = −21→21 |
3181 independent reflections | l = −29→29 |
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)] = 0.077 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.156 | H atoms treated by a mixture of independent and constrained refinement |
S = 1.17 | w = 1/[σ2(Fo2) + (0.0475P)2 + 0.2413P] where P = (Fo2 + 2Fc2)/3 |
3181 reflections | (Δ/σ)max < 0.001 |
305 parameters | Δρmax = 0.11 e Å−3 |
0 restraints | Δρmin = −0.17 e Å−3 |
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
x | y | z | Uiso*/Ueq | ||
O1 | −0.0119 (5) | 0.7437 (2) | −0.27775 (12) | 0.0905 (9) | |
N1 | 0.2999 (5) | 0.3978 (2) | 0.14753 (15) | 0.0677 (8) | |
N2 | 0.1208 (5) | 0.54726 (19) | 0.02282 (14) | 0.0641 (8) | |
N3 | −0.0605 (5) | 0.5927 (2) | 0.02152 (14) | 0.0652 (8) | |
N4 | −0.2452 (6) | 0.7983 (2) | −0.20133 (16) | 0.0736 (9) | |
C1 | 0.5090 (8) | 0.4326 (3) | −0.02206 (19) | 0.0743 (10) | |
C2 | 0.6804 (8) | 0.4038 (3) | −0.0613 (2) | 0.0813 (12) | |
C3 | 0.8470 (8) | 0.3492 (3) | −0.0376 (2) | 0.0818 (12) | |
C4 | 0.8443 (7) | 0.3239 (3) | 0.0263 (2) | 0.0740 (11) | |
C5 | 0.6764 (7) | 0.3532 (3) | 0.0666 (2) | 0.0684 (10) | |
C6 | 0.5040 (6) | 0.4078 (2) | 0.04375 (17) | 0.0613 (8) | |
C7 | 0.3234 (6) | 0.4368 (2) | 0.08750 (17) | 0.0612 (9) | |
C8 | 0.1165 (7) | 0.4341 (2) | 0.17957 (17) | 0.0650 (9) | |
C9 | 0.0324 (8) | 0.4120 (3) | 0.2403 (2) | 0.0789 (11) | |
C10 | −0.1572 (8) | 0.4562 (3) | 0.2605 (2) | 0.0849 (12) | |
C11 | −0.2579 (8) | 0.5207 (3) | 0.2210 (2) | 0.0820 (12) | |
C12 | −0.1759 (7) | 0.5424 (3) | 0.1604 (2) | 0.0715 (10) | |
C13 | 0.0188 (6) | 0.4985 (2) | 0.13894 (16) | 0.0618 (8) | |
C14 | 0.1516 (6) | 0.4997 (2) | 0.08021 (16) | 0.0592 (8) | |
C15 | −0.0925 (6) | 0.6413 (2) | −0.03707 (18) | 0.0605 (9) | |
C16 | −0.2977 (7) | 0.6838 (3) | −0.04350 (19) | 0.0682 (10) | |
C17 | −0.3449 (7) | 0.7345 (2) | −0.09798 (18) | 0.0680 (10) | |
C18 | −0.1876 (6) | 0.7449 (2) | −0.14677 (17) | 0.0640 (9) | |
C19 | 0.0209 (7) | 0.7045 (3) | −0.1396 (2) | 0.0792 (12) | |
C20 | 0.0656 (7) | 0.6525 (3) | −0.0855 (2) | 0.0756 (11) | |
C21 | −0.1663 (8) | 0.7929 (3) | −0.26273 (19) | 0.0780 (11) | |
C22 | −0.2833 (10) | 0.8514 (4) | −0.3109 (2) | 0.1159 (19) | |
H1 | 0.391 (6) | 0.355 (2) | 0.1633 (18) | 0.078 (12)* | |
H4 | −0.354 (7) | 0.831 (3) | −0.1949 (17) | 0.075 (13)* | |
H11 | 0.388 (7) | 0.473 (2) | −0.0394 (16) | 0.077 (11)* | |
H21 | 0.677 (7) | 0.420 (2) | −0.1068 (19) | 0.084 (12)* | |
H22A | −0.1772 | 0.8903 | −0.3318 | 0.174* | |
H22B | −0.3932 | 0.8874 | −0.2889 | 0.174* | |
H22C | −0.3551 | 0.8141 | −0.3429 | 0.174* | |
H31 | 0.973 (7) | 0.329 (2) | −0.0660 (17) | 0.080 (11)* | |
H41 | 0.962 (7) | 0.286 (3) | 0.0433 (17) | 0.084 (12)* | |
H51 | 0.683 (6) | 0.334 (2) | 0.1089 (16) | 0.058 (10)* | |
H91 | 0.106 (8) | 0.369 (3) | 0.268 (2) | 0.104 (15)* | |
H101 | −0.218 (7) | 0.448 (3) | 0.3020 (19) | 0.086 (13)* | |
H111 | −0.395 (6) | 0.549 (3) | 0.2371 (18) | 0.086 (12)* | |
H121 | −0.260 (6) | 0.585 (2) | 0.1321 (15) | 0.062 (10)* | |
H161 | −0.410 (7) | 0.678 (2) | −0.0073 (17) | 0.084 (12)* | |
H171 | −0.490 (8) | 0.766 (3) | −0.1032 (19) | 0.098 (13)* | |
H191 | 0.119 (7) | 0.710 (3) | −0.1721 (19) | 0.090 (14)* | |
H201 | 0.221 (8) | 0.623 (3) | −0.076 (2) | 0.117 (15)* |
Atomic displacement parameters (Å2) top
U11 | U22 | U33 | U12 | U13 | U23 | |
O1 | 0.101 (2) | 0.098 (2) | 0.0726 (16) | 0.032 (2) | 0.0059 (17) | −0.0093 (15) |
N1 | 0.068 (2) | 0.0642 (18) | 0.0708 (19) | 0.0074 (16) | −0.0098 (17) | 0.0052 (16) |
N2 | 0.0603 (18) | 0.0581 (16) | 0.0739 (19) | 0.0018 (15) | −0.0123 (15) | −0.0040 (14) |
N3 | 0.0629 (18) | 0.0610 (16) | 0.0716 (19) | 0.0014 (16) | −0.0118 (15) | −0.0008 (15) |
N4 | 0.080 (2) | 0.075 (2) | 0.0663 (19) | 0.027 (2) | −0.0016 (17) | −0.0025 (16) |
C1 | 0.077 (3) | 0.071 (2) | 0.075 (3) | 0.010 (2) | −0.009 (2) | 0.000 (2) |
C2 | 0.087 (3) | 0.083 (3) | 0.074 (3) | 0.001 (3) | 0.004 (2) | −0.004 (2) |
C3 | 0.073 (3) | 0.075 (3) | 0.097 (3) | 0.001 (2) | 0.011 (3) | −0.009 (2) |
C4 | 0.067 (2) | 0.067 (2) | 0.089 (3) | 0.006 (2) | −0.004 (2) | −0.002 (2) |
C5 | 0.069 (2) | 0.066 (2) | 0.070 (2) | −0.004 (2) | −0.009 (2) | −0.0025 (19) |
C6 | 0.063 (2) | 0.0523 (18) | 0.068 (2) | −0.0008 (18) | −0.0113 (18) | −0.0086 (16) |
C7 | 0.060 (2) | 0.0545 (19) | 0.069 (2) | 0.0009 (17) | −0.0120 (18) | −0.0040 (16) |
C8 | 0.065 (2) | 0.062 (2) | 0.069 (2) | 0.0002 (18) | −0.0064 (18) | −0.0048 (17) |
C9 | 0.086 (3) | 0.073 (3) | 0.077 (3) | 0.003 (2) | 0.000 (2) | 0.002 (2) |
C10 | 0.092 (3) | 0.082 (3) | 0.080 (3) | −0.010 (3) | 0.012 (3) | −0.001 (2) |
C11 | 0.076 (3) | 0.079 (3) | 0.091 (3) | −0.004 (2) | 0.009 (2) | −0.009 (2) |
C12 | 0.066 (2) | 0.060 (2) | 0.088 (3) | −0.001 (2) | −0.006 (2) | −0.007 (2) |
C13 | 0.061 (2) | 0.0553 (18) | 0.069 (2) | −0.0042 (17) | −0.0098 (18) | −0.0091 (17) |
C14 | 0.059 (2) | 0.0537 (18) | 0.065 (2) | −0.0028 (17) | −0.0107 (18) | −0.0060 (16) |
C15 | 0.060 (2) | 0.0525 (18) | 0.069 (2) | 0.0005 (17) | −0.0071 (18) | −0.0061 (16) |
C16 | 0.068 (2) | 0.070 (2) | 0.067 (2) | 0.013 (2) | 0.001 (2) | −0.0008 (19) |
C17 | 0.065 (2) | 0.066 (2) | 0.072 (2) | 0.021 (2) | 0.002 (2) | −0.0066 (18) |
C18 | 0.071 (2) | 0.0586 (19) | 0.062 (2) | 0.0109 (19) | −0.008 (2) | −0.0067 (17) |
C19 | 0.065 (2) | 0.097 (3) | 0.076 (3) | 0.017 (2) | 0.003 (2) | 0.007 (2) |
C20 | 0.058 (2) | 0.088 (3) | 0.081 (3) | 0.010 (2) | −0.007 (2) | 0.005 (2) |
C21 | 0.089 (3) | 0.075 (2) | 0.070 (2) | 0.014 (2) | 0.001 (2) | −0.011 (2) |
C22 | 0.143 (5) | 0.129 (4) | 0.075 (3) | 0.063 (4) | −0.003 (3) | 0.010 (3) |
Geometric parameters (Å, º) top
O1—C21 | 1.217 (5) | C10—H101 | 0.94 (4) |
N1—C7 | 1.368 (4) | C11—C12 | 1.376 (6) |
N1—C8 | 1.390 (5) | C11—C10 | 1.390 (6) |
N1—H1 | 0.89 (4) | C11—H111 | 0.98 (4) |
N3—N2 | 1.278 (4) | C12—H121 | 0.99 (3) |
N3—C15 | 1.414 (4) | C13—C8 | 1.395 (5) |
N4—C21 | 1.349 (5) | C13—C12 | 1.407 (5) |
N4—C18 | 1.413 (5) | C14—N2 | 1.385 (4) |
N4—H4 | 0.83 (4) | C14—C7 | 1.396 (5) |
C1—C2 | 1.374 (6) | C14—C13 | 1.445 (5) |
C1—H11 | 1.01 (4) | C15—C20 | 1.383 (5) |
C2—H21 | 0.97 (4) | C15—C16 | 1.388 (5) |
C3—C4 | 1.364 (6) | C16—H161 | 1.01 (4) |
C3—C2 | 1.373 (6) | C17—C16 | 1.376 (5) |
C3—H31 | 1.00 (4) | C17—H171 | 0.99 (4) |
C4—H41 | 0.97 (4) | C18—C17 | 1.384 (5) |
C5—C4 | 1.374 (6) | C18—C19 | 1.394 (5) |
C5—H51 | 0.91 (3) | C19—C20 | 1.378 (6) |
C6—C5 | 1.392 (5) | C19—H191 | 0.89 (4) |
C6—C1 | 1.400 (5) | C20—H201 | 1.05 (5) |
C6—C7 | 1.471 (5) | C21—C22 | 1.489 (6) |
C8—C9 | 1.385 (5) | C22—H22A | 0.9600 |
C9—H91 | 0.96 (4) | C22—H22B | 0.9600 |
C10—C9 | 1.375 (6) | C22—H22C | 0.9600 |
C7—N1—C8 | 110.2 (3) | C12—C11—H111 | 120 (2) |
C7—N1—H1 | 124 (2) | C10—C11—H111 | 118 (2) |
C8—N1—H1 | 126 (2) | C11—C12—C13 | 118.2 (4) |
N3—N2—C14 | 113.4 (3) | C11—C12—H121 | 119.8 (19) |
N2—N3—C15 | 113.6 (3) | C13—C12—H121 | 122.0 (19) |
C21—N4—C18 | 128.5 (3) | C8—C13—C12 | 118.5 (4) |
C21—N4—H4 | 117 (3) | C8—C13—C14 | 106.0 (3) |
C18—N4—H4 | 113 (3) | C12—C13—C14 | 135.4 (3) |
C2—C1—C6 | 120.1 (4) | N2—C14—C7 | 121.9 (3) |
C2—C1—H11 | 121 (2) | N2—C14—C13 | 130.0 (3) |
C6—C1—H11 | 118.8 (19) | C7—C14—C13 | 108.0 (3) |
C3—C2—C1 | 121.2 (4) | C20—C15—C16 | 119.0 (3) |
C3—C2—H21 | 120 (3) | C20—C15—N3 | 125.4 (3) |
C1—C2—H21 | 118 (3) | C16—C15—N3 | 115.5 (3) |
C4—C3—C2 | 119.6 (4) | C17—C16—C15 | 120.4 (4) |
C4—C3—H31 | 119 (2) | C17—C16—H161 | 121 (2) |
C2—C3—H31 | 121 (2) | C15—C16—H161 | 119 (2) |
C3—C4—C5 | 120.1 (4) | C16—C17—C18 | 120.6 (4) |
C3—C4—H41 | 120 (2) | C16—C17—H171 | 121 (2) |
C5—C4—H41 | 120 (2) | C18—C17—H171 | 118 (2) |
C4—C5—C6 | 121.6 (4) | C17—C18—C19 | 119.2 (4) |
C4—C5—H51 | 116 (2) | C17—C18—N4 | 118.0 (3) |
C6—C5—H51 | 122 (2) | C19—C18—N4 | 122.8 (4) |
C5—C6—C1 | 117.5 (4) | C20—C19—C18 | 119.9 (4) |
C5—C6—C7 | 120.6 (3) | C20—C19—H191 | 122 (3) |
C1—C6—C7 | 121.9 (3) | C18—C19—H191 | 118 (3) |
N1—C7—C14 | 107.5 (3) | C19—C20—C15 | 120.9 (4) |
N1—C7—C6 | 120.2 (3) | C19—C20—H201 | 124 (3) |
C14—C7—C6 | 132.2 (3) | C15—C20—H201 | 115 (3) |
C9—C8—N1 | 128.5 (4) | O1—C21—N4 | 122.6 (4) |
C9—C8—C13 | 123.2 (4) | O1—C21—C22 | 122.5 (4) |
N1—C8—C13 | 108.3 (3) | N4—C21—C22 | 114.9 (4) |
C10—C9—C8 | 117.3 (4) | C21—C22—H22A | 109.5 |
C10—C9—H91 | 121 (3) | C21—C22—H22B | 109.5 |
C8—C9—H91 | 121 (3) | H22A—C22—H22B | 109.5 |
C9—C10—C11 | 120.7 (5) | C21—C22—H22C | 109.5 |
C9—C10—H101 | 122 (3) | H22A—C22—H22C | 109.5 |
C11—C10—H101 | 117 (3) | H22B—C22—H22C | 109.5 |
C12—C11—C10 | 122.1 (4) | ||
C8—N1—C7—C14 | −0.1 (4) | C10—C11—C12—C13 | −1.3 (6) |
C8—N1—C7—C6 | −178.7 (3) | C8—C13—C12—C11 | 1.1 (5) |
C7—N1—C8—C9 | 178.5 (4) | C14—C13—C12—C11 | 178.1 (4) |
C7—N1—C8—C13 | 0.0 (4) | C12—C13—C8—C9 | −0.7 (5) |
C15—N3—N2—C14 | −180.0 (3) | C14—C13—C8—C9 | −178.5 (3) |
N2—N3—C15—C20 | −9.7 (5) | C12—C13—C8—N1 | 177.9 (3) |
N2—N3—C15—C16 | 173.4 (3) | C14—C13—C8—N1 | 0.1 (4) |
C21—N4—C18—C17 | −153.1 (4) | C7—C14—N2—N3 | 171.2 (3) |
C21—N4—C18—C19 | 28.3 (6) | C13—C14—N2—N3 | −4.3 (5) |
C18—N4—C21—O1 | −7.3 (7) | N2—C14—C13—C8 | 175.8 (3) |
C18—N4—C21—C22 | 172.4 (4) | C7—C14—C13—C8 | −0.1 (4) |
C6—C1—C2—C3 | 1.2 (7) | N2—C14—C13—C12 | −1.5 (6) |
C4—C3—C2—C1 | −0.8 (7) | C7—C14—C13—C12 | −177.4 (4) |
C2—C3—C4—C5 | −0.3 (6) | N2—C14—C7—N1 | −176.2 (3) |
C6—C5—C4—C3 | 1.0 (6) | C13—C14—C7—N1 | 0.2 (4) |
C1—C6—C5—C4 | −0.6 (5) | N2—C14—C7—C6 | 2.2 (5) |
C7—C6—C5—C4 | 178.7 (3) | C13—C14—C7—C6 | 178.5 (3) |
C5—C6—C7—N1 | −11.9 (5) | C20—C15—C16—C17 | 1.5 (6) |
C1—C6—C7—N1 | 167.4 (3) | N3—C15—C16—C17 | 178.7 (3) |
C5—C6—C7—C14 | 169.9 (3) | C16—C15—C20—C19 | −0.4 (6) |
C1—C6—C7—C14 | −10.8 (6) | N3—C15—C20—C19 | −177.2 (4) |
C5—C6—C1—C2 | −0.5 (5) | C18—C17—C16—C15 | −0.9 (6) |
C7—C6—C1—C2 | −179.8 (4) | C19—C18—C17—C16 | −1.0 (6) |
N1—C8—C9—C10 | −177.9 (4) | N4—C18—C17—C16 | −179.6 (3) |
C13—C8—C9—C10 | 0.3 (6) | C17—C18—C19—C20 | 2.1 (6) |
C11—C10—C9—C8 | −0.4 (6) | N4—C18—C19—C20 | −179.3 (4) |
C12—C11—C10—C9 | 0.9 (7) | C18—C19—C20—C15 | −1.5 (6) |