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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
Key indicators
- Single-crystal X-ray study
- T = 296 K
- Mean (C-C) = 0.006 Å
- R factor = 0.077
- wR factor = 0.156
- Data-to-parameter ratio = 10.4
checkCIF/PLATON results
No syntax errors found
Alert level C PLAT340_ALERT_3_C Low Bond Precision on C-C bonds (x 1000) Ang ... 6 PLAT420_ALERT_2_C D-H Without Acceptor N4 - H4 ... ?
Alert level G REFLT03_ALERT_4_G Please check that the estimate of the number of Friedel pairs is correct. If it is not, please give the correct count in the _publ_section_exptl_refinement section of the submitted CIF. From the CIF: _diffrn_reflns_theta_max 30.58 From the CIF: _reflns_number_total 3181 Count of symmetry unique reflns 3192 Completeness (_total/calc) 99.66% TEST3: Check Friedels for noncentro structure Estimate of Friedel pairs measured 0 Fraction of Friedel pairs measured 0.000 Are heavy atom types Z>Si present no
0 ALERT level A = In general: serious problem 0 ALERT level B = Potentially serious problem 2 ALERT level C = Check and explain 1 ALERT level G = General alerts; check 0 ALERT type 1 CIF construction/syntax error, inconsistent or missing data 1 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 1 ALERT type 4 Improvement, methodology, query or suggestion 0 ALERT type 5 Informative message, check
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) |
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