Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536807032655/hb2473sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S1600536807032655/hb2473Isup2.hkl |
CCDC reference: 657736
Indol-3-yl-acetylhydrazine (0.30 g, 1.6 mmol) and indol-3-ylcarboxaldehyde (0.20 g, 1.6 mmol) were heated in ethanol (50 ml) for 2 h. The solution was filtered; slow evaporation of the solvent yielded faint yellow needles of (I).
Anomalouse dispersion was negligible and Friedel pairs were merged before refinement. All hydrogen atoms were located in difference Fourier maps, and were refined with distance restraints C—H = 1.00±0.01 Å and N–H = 0.88±0.01 Å. Their Uiso values were freely refined. Friedel pairs were merged.
A previous study reported 2'-[(5-chloro-1H-indol-3-yl)methylene]-2-(1H-indol-3-yl)acetohydrazide, a compound that is N–H···O hydrogen bonded into a three-dimensional network (Ali et al., 2007). Although there are three possible donor sites, the site belonging to the indolyl ring that is linked to the methylene unit is not involved in the H bond interactions. A similar type of hydrogen bonding (Table 1) is found in the unsubstituted title compound, (I), (Fig. 1).
For a related crystal structure, see Ali et al. (2007).
Data collection: APEX2 (Bruker, 2005); cell refinement: SAINT (Bruker, 2005); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: X-SEED (Barbour, 2001); software used to prepare material for publication: publCIF (Westrip, 2007).
Fig. 1. View of (I) with displacement ellipsoids drawn at the 70% probability level, and H atoms as spheres of arbitrary radius. |
C19H16N4O | F(000) = 664 |
Mr = 316.36 | Dx = 1.303 Mg m−3 |
Monoclinic, Cc | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: C -2yc | Cell parameters from 8692 reflections |
a = 14.0350 (2) Å | θ = 2.8–30.2° |
b = 14.4517 (2) Å | µ = 0.08 mm−1 |
c = 8.1372 (1) Å | T = 293 K |
β = 102.193 (1)° | Tapered needle, light yellow |
V = 1613.23 (4) Å3 | 0.60 × 0.15 × 0.10 mm |
Z = 4 |
Bruker APEXII CCD area-detector diffractometer | 2260 reflections with I > 2σ(I) |
Radiation source: medium-focus sealed tube | Rint = 0.023 |
Graphite monochromator | θmax = 30.0°, θmin = 2.1° |
φ and ω scans | h = −19→19 |
12370 measured reflections | k = −20→20 |
2340 independent reflections | l = −11→11 |
Refinement on F2 | Secondary atom site location: difference Fourier map |
Least-squares matrix: full | Hydrogen site location: inferred from neighbouring sites |
R[F2 > 2σ(F2)] = 0.034 | H atoms treated by a mixture of independent and constrained refinement |
wR(F2) = 0.100 | w = 1/[σ2(Fo2) + (0.0767P)2 + 0.0497P] where P = (Fo2 + 2Fc2)/3 |
S = 1.17 | (Δ/σ)max = 0.001 |
2340 reflections | Δρmax = 0.38 e Å−3 |
281 parameters | Δρmin = −0.26 e Å−3 |
17 restraints | Absolute structure: Friedel pairs were merged |
Primary atom site location: structure-invariant direct methods |
C19H16N4O | V = 1613.23 (4) Å3 |
Mr = 316.36 | Z = 4 |
Monoclinic, Cc | Mo Kα radiation |
a = 14.0350 (2) Å | µ = 0.08 mm−1 |
b = 14.4517 (2) Å | T = 293 K |
c = 8.1372 (1) Å | 0.60 × 0.15 × 0.10 mm |
β = 102.193 (1)° |
Bruker APEXII CCD area-detector diffractometer | 2260 reflections with I > 2σ(I) |
12370 measured reflections | Rint = 0.023 |
2340 independent reflections |
R[F2 > 2σ(F2)] = 0.034 | 17 restraints |
wR(F2) = 0.100 | H atoms treated by a mixture of independent and constrained refinement |
S = 1.17 | Δρmax = 0.38 e Å−3 |
2340 reflections | Δρmin = −0.26 e Å−3 |
281 parameters | Absolute structure: Friedel pairs were merged |
x | y | z | Uiso*/Ueq | ||
O1 | 0.50000 (8) | 0.58900 (8) | 0.50001 (14) | 0.0172 (2) | |
N1 | 0.86357 (11) | 0.22337 (10) | 0.56290 (18) | 0.0207 (3) | |
N2 | 0.62106 (9) | 0.44789 (8) | 0.44976 (15) | 0.0139 (2) | |
N3 | 0.55394 (9) | 0.49082 (9) | 0.32082 (15) | 0.0143 (2) | |
N4 | 0.20100 (11) | 0.47912 (12) | 0.2027 (2) | 0.0279 (3) | |
C1 | 0.87353 (11) | 0.28098 (11) | 0.7011 (2) | 0.0176 (3) | |
C2 | 0.94407 (13) | 0.28031 (13) | 0.8506 (2) | 0.0236 (3) | |
C3 | 0.93560 (13) | 0.34678 (13) | 0.9698 (2) | 0.0260 (3) | |
C4 | 0.85926 (14) | 0.41173 (13) | 0.9415 (2) | 0.0247 (3) | |
C5 | 0.79050 (12) | 0.41325 (11) | 0.7917 (2) | 0.0193 (3) | |
C6 | 0.79757 (10) | 0.34736 (10) | 0.66815 (18) | 0.0150 (3) | |
C7 | 0.78624 (12) | 0.25238 (12) | 0.44324 (19) | 0.0204 (3) | |
C8 | 0.74261 (11) | 0.32866 (10) | 0.50057 (19) | 0.0160 (3) | |
C9 | 0.66442 (11) | 0.37875 (10) | 0.39548 (18) | 0.0154 (3) | |
C10 | 0.49922 (10) | 0.56129 (9) | 0.35533 (18) | 0.0134 (2) | |
C11 | 0.43239 (10) | 0.60328 (10) | 0.20165 (19) | 0.0152 (3) | |
C12 | 0.30093 (12) | 0.48812 (12) | 0.2490 (2) | 0.0226 (3) | |
C13 | 0.33009 (11) | 0.56780 (10) | 0.18153 (18) | 0.0154 (3) | |
C14 | 0.24281 (10) | 0.61075 (10) | 0.08736 (18) | 0.0155 (3) | |
C15 | 0.22490 (11) | 0.69156 (11) | −0.0099 (2) | 0.0193 (3) | |
C16 | 0.12907 (13) | 0.71310 (12) | −0.0859 (2) | 0.0246 (3) | |
C17 | 0.05120 (13) | 0.65631 (15) | −0.0636 (2) | 0.0274 (4) | |
C18 | 0.06691 (12) | 0.57637 (15) | 0.0317 (2) | 0.0276 (4) | |
C19 | 0.16355 (12) | 0.55390 (12) | 0.1053 (2) | 0.0212 (3) | |
H1n | 0.906 (2) | 0.1812 (18) | 0.551 (4) | 0.046 (8)* | |
H3n | 0.5469 (17) | 0.4733 (16) | 0.2169 (15) | 0.017 (5)* | |
H4n | 0.167 (2) | 0.4364 (17) | 0.242 (4) | 0.041 (8)* | |
H2 | 0.9927 (18) | 0.2299 (16) | 0.860 (4) | 0.041 (8)* | |
H3 | 0.9847 (16) | 0.348 (2) | 1.079 (2) | 0.034 (7)* | |
H4 | 0.851 (2) | 0.4539 (18) | 1.034 (3) | 0.041 (7)* | |
H5 | 0.7363 (14) | 0.4593 (15) | 0.772 (3) | 0.027 (6)* | |
H7 | 0.7666 (19) | 0.2195 (16) | 0.334 (2) | 0.026 (6)* | |
H9 | 0.6452 (19) | 0.3595 (18) | 0.2750 (15) | 0.025 (6)* | |
H11A | 0.4299 (18) | 0.6713 (7) | 0.218 (3) | 0.022 (6)* | |
H11B | 0.4619 (17) | 0.5947 (18) | 0.101 (2) | 0.024 (6)* | |
H12 | 0.341 (2) | 0.439 (2) | 0.309 (4) | 0.034 (7)* | |
H15 | 0.2789 (15) | 0.7343 (17) | −0.021 (4) | 0.032 (7)* | |
H16 | 0.117 (2) | 0.7690 (13) | −0.159 (3) | 0.037 (8)* | |
H17 | −0.0162 (10) | 0.6719 (19) | −0.124 (3) | 0.032 (7)* | |
H18 | 0.0150 (16) | 0.5337 (17) | 0.050 (4) | 0.037 (7)* |
U11 | U22 | U33 | U12 | U13 | U23 | |
O1 | 0.0198 (5) | 0.0187 (5) | 0.0121 (5) | 0.0055 (4) | 0.0011 (4) | −0.0006 (4) |
N1 | 0.0239 (6) | 0.0203 (6) | 0.0181 (6) | 0.0101 (5) | 0.0049 (5) | 0.0000 (5) |
N2 | 0.0131 (5) | 0.0155 (5) | 0.0118 (6) | 0.0026 (4) | 0.0000 (4) | 0.0025 (4) |
N3 | 0.0158 (5) | 0.0172 (5) | 0.0088 (5) | 0.0037 (4) | 0.0001 (4) | −0.0002 (4) |
N4 | 0.0196 (7) | 0.0330 (8) | 0.0278 (7) | −0.0075 (5) | −0.0029 (5) | 0.0127 (6) |
C1 | 0.0175 (6) | 0.0186 (6) | 0.0167 (7) | 0.0046 (5) | 0.0034 (5) | 0.0022 (5) |
C2 | 0.0198 (7) | 0.0287 (8) | 0.0207 (8) | 0.0060 (6) | 0.0005 (6) | 0.0044 (6) |
C3 | 0.0236 (7) | 0.0316 (8) | 0.0187 (8) | 0.0000 (6) | −0.0046 (6) | −0.0001 (6) |
C4 | 0.0268 (8) | 0.0263 (8) | 0.0187 (7) | −0.0013 (6) | −0.0007 (6) | −0.0057 (6) |
C5 | 0.0210 (7) | 0.0180 (7) | 0.0181 (7) | 0.0027 (5) | 0.0022 (5) | −0.0031 (5) |
C6 | 0.0147 (6) | 0.0151 (6) | 0.0149 (6) | 0.0029 (4) | 0.0024 (5) | 0.0006 (5) |
C7 | 0.0244 (7) | 0.0199 (7) | 0.0163 (7) | 0.0065 (5) | 0.0033 (5) | −0.0023 (5) |
C8 | 0.0174 (6) | 0.0157 (6) | 0.0141 (6) | 0.0040 (5) | 0.0017 (5) | −0.0001 (5) |
C9 | 0.0163 (6) | 0.0170 (6) | 0.0122 (6) | 0.0026 (5) | 0.0009 (5) | 0.0001 (5) |
C10 | 0.0123 (5) | 0.0147 (5) | 0.0122 (6) | 0.0014 (4) | 0.0004 (4) | 0.0024 (5) |
C11 | 0.0141 (6) | 0.0176 (6) | 0.0125 (6) | 0.0027 (5) | −0.0005 (5) | 0.0038 (5) |
C12 | 0.0198 (7) | 0.0254 (7) | 0.0196 (7) | −0.0031 (6) | −0.0027 (6) | 0.0074 (6) |
C13 | 0.0150 (6) | 0.0177 (6) | 0.0123 (6) | 0.0010 (5) | −0.0001 (5) | 0.0013 (5) |
C14 | 0.0149 (6) | 0.0186 (6) | 0.0121 (6) | 0.0019 (5) | 0.0010 (5) | −0.0014 (5) |
C15 | 0.0189 (7) | 0.0195 (6) | 0.0180 (7) | 0.0048 (5) | 0.0005 (5) | 0.0001 (5) |
C16 | 0.0222 (8) | 0.0244 (7) | 0.0246 (8) | 0.0086 (6) | −0.0010 (6) | 0.0016 (6) |
C17 | 0.0174 (7) | 0.0389 (9) | 0.0231 (8) | 0.0073 (6) | −0.0018 (6) | −0.0001 (7) |
C18 | 0.0157 (7) | 0.0402 (9) | 0.0250 (8) | −0.0026 (6) | −0.0001 (6) | 0.0007 (7) |
C19 | 0.0173 (6) | 0.0279 (8) | 0.0170 (7) | −0.0019 (5) | 0.0005 (5) | 0.0032 (6) |
O1—C10 | 1.2414 (19) | C7—C8 | 1.389 (2) |
N1—C7 | 1.362 (2) | C7—H7 | 0.996 (10) |
N1—C1 | 1.382 (2) | C8—C9 | 1.436 (2) |
N1—H1n | 0.876 (10) | C9—H9 | 1.000 (10) |
N2—C9 | 1.2952 (18) | C10—C11 | 1.5220 (19) |
N2—N3 | 1.3985 (16) | C11—C13 | 1.501 (2) |
N3—C10 | 1.3405 (18) | C11—H11A | 0.994 (10) |
N3—H3n | 0.868 (10) | C11—H11B | 1.000 (10) |
N4—C19 | 1.377 (2) | C12—C13 | 1.375 (2) |
N4—C12 | 1.379 (2) | C12—H12 | 0.97 (3) |
N4—H4n | 0.883 (10) | C13—C14 | 1.4410 (19) |
C1—C2 | 1.397 (2) | C14—C15 | 1.403 (2) |
C1—C6 | 1.4171 (19) | C14—C19 | 1.415 (2) |
C2—C3 | 1.388 (3) | C15—C16 | 1.392 (2) |
C2—H2 | 0.991 (10) | C15—H15 | 0.996 (10) |
C3—C4 | 1.406 (3) | C16—C17 | 1.409 (3) |
C3—H3 | 1.002 (10) | C16—H16 | 0.998 (10) |
C4—C5 | 1.386 (2) | C17—C18 | 1.383 (3) |
C4—H4 | 0.993 (10) | C17—H17 | 0.994 (10) |
C5—C6 | 1.404 (2) | C18—C19 | 1.400 (2) |
C5—H5 | 0.998 (10) | C18—H18 | 0.991 (10) |
C6—C8 | 1.443 (2) | ||
C7—N1—C1 | 108.94 (12) | N2—C9—H9 | 120.0 (16) |
C7—N1—H1n | 127 (2) | C8—C9—H9 | 117.2 (16) |
C1—N1—H1n | 124 (2) | O1—C10—N3 | 123.58 (13) |
C9—N2—N3 | 112.15 (12) | O1—C10—C11 | 122.08 (13) |
C10—N3—N2 | 120.32 (12) | N3—C10—C11 | 114.31 (13) |
C10—N3—H3n | 118.3 (16) | C13—C11—C10 | 111.28 (12) |
N2—N3—H3n | 121.4 (16) | C13—C11—H11A | 107.0 (15) |
C19—N4—C12 | 109.00 (14) | C10—C11—H11A | 108.4 (14) |
C19—N4—H4n | 126 (2) | C13—C11—H11B | 114.9 (15) |
C12—N4—H4n | 124 (2) | C10—C11—H11B | 109.4 (15) |
N1—C1—C2 | 129.47 (15) | H11A—C11—H11B | 106 (2) |
N1—C1—C6 | 108.12 (13) | C13—C12—N4 | 109.95 (14) |
C2—C1—C6 | 122.40 (15) | C13—C12—H12 | 128.8 (18) |
C3—C2—C1 | 117.02 (15) | N4—C12—H12 | 120.8 (18) |
C3—C2—H2 | 128.1 (19) | C12—C13—C14 | 106.37 (13) |
C1—C2—H2 | 114.8 (19) | C12—C13—C11 | 126.96 (13) |
C2—C3—C4 | 121.48 (15) | C14—C13—C11 | 126.67 (13) |
C2—C3—H3 | 118.9 (17) | C15—C14—C19 | 119.35 (14) |
C4—C3—H3 | 119.6 (17) | C15—C14—C13 | 133.57 (14) |
C5—C4—C3 | 121.32 (16) | C19—C14—C13 | 107.08 (13) |
C5—C4—H4 | 119.3 (19) | C16—C15—C14 | 118.55 (15) |
C3—C4—H4 | 119.2 (19) | C16—C15—H15 | 120.2 (17) |
C4—C5—C6 | 118.54 (15) | C14—C15—H15 | 121.2 (17) |
C4—C5—H5 | 121.0 (16) | C15—C16—C17 | 121.05 (16) |
C6—C5—H5 | 120.4 (16) | C15—C16—H16 | 117.9 (17) |
C5—C6—C1 | 119.21 (14) | C17—C16—H16 | 121.1 (17) |
C5—C6—C8 | 134.37 (14) | C18—C17—C16 | 121.51 (15) |
C1—C6—C8 | 106.42 (13) | C18—C17—H17 | 119.1 (17) |
N1—C7—C8 | 110.21 (14) | C16—C17—H17 | 119.3 (17) |
N1—C7—H7 | 121.4 (15) | C17—C18—C19 | 117.31 (16) |
C8—C7—H7 | 128.4 (15) | C17—C18—H18 | 124.8 (18) |
C7—C8—C9 | 122.39 (14) | C19—C18—H18 | 117.9 (18) |
C7—C8—C6 | 106.28 (13) | N4—C19—C18 | 130.20 (16) |
C9—C8—C6 | 131.06 (13) | N4—C19—C14 | 107.59 (14) |
N2—C9—C8 | 122.73 (13) | C18—C19—C14 | 122.20 (16) |
C9—N2—N3—C10 | 177.12 (13) | N2—N3—C10—C11 | 177.81 (12) |
C7—N1—C1—C2 | −177.43 (18) | O1—C10—C11—C13 | −78.13 (17) |
C7—N1—C1—C6 | 1.60 (18) | N3—C10—C11—C13 | 99.87 (15) |
N1—C1—C2—C3 | −179.51 (17) | C19—N4—C12—C13 | −0.6 (2) |
C6—C1—C2—C3 | 1.6 (3) | N4—C12—C13—C14 | −0.1 (2) |
C1—C2—C3—C4 | 0.2 (3) | N4—C12—C13—C11 | 179.88 (16) |
C2—C3—C4—C5 | −1.4 (3) | C10—C11—C13—C12 | −20.7 (2) |
C3—C4—C5—C6 | 0.8 (3) | C10—C11—C13—C14 | 159.29 (14) |
C4—C5—C6—C1 | 0.9 (2) | C12—C13—C14—C15 | −179.13 (17) |
C4—C5—C6—C8 | −178.63 (17) | C11—C13—C14—C15 | 0.9 (3) |
N1—C1—C6—C5 | 178.76 (14) | C12—C13—C14—C19 | 0.75 (17) |
C2—C1—C6—C5 | −2.1 (2) | C11—C13—C14—C19 | −179.23 (15) |
N1—C1—C6—C8 | −1.63 (17) | C19—C14—C15—C16 | 0.0 (2) |
C2—C1—C6—C8 | 177.48 (15) | C13—C14—C15—C16 | 179.90 (17) |
C1—N1—C7—C8 | −0.93 (19) | C14—C15—C16—C17 | 1.2 (2) |
N1—C7—C8—C9 | 174.55 (14) | C15—C16—C17—C18 | −1.1 (3) |
N1—C7—C8—C6 | −0.11 (19) | C16—C17—C18—C19 | −0.1 (3) |
C5—C6—C8—C7 | −179.41 (17) | C12—N4—C19—C18 | −178.80 (19) |
C1—C6—C8—C7 | 1.06 (17) | C12—N4—C19—C14 | 1.1 (2) |
C5—C6—C8—C9 | 6.6 (3) | C17—C18—C19—N4 | −178.77 (19) |
C1—C6—C8—C9 | −172.95 (16) | C17—C18—C19—C14 | 1.4 (3) |
N3—N2—C9—C8 | 174.31 (13) | C15—C14—C19—N4 | 178.78 (15) |
C7—C8—C9—N2 | 177.46 (15) | C13—C14—C19—N4 | −1.13 (18) |
C6—C8—C9—N2 | −9.3 (3) | C15—C14—C19—C18 | −1.3 (2) |
N2—N3—C10—O1 | −4.2 (2) | C13—C14—C19—C18 | 178.77 (16) |
D—H···A | D—H | H···A | D···A | D—H···A |
N1—H1N···O1i | 0.88 (1) | 1.98 (1) | 2.848 (2) | 174 (3) |
N3—H3N···O1ii | 0.87 (1) | 1.97 (1) | 2.808 (2) | 163 (2) |
Symmetry codes: (i) x+1/2, y−1/2, z; (ii) x, −y+1, z−1/2. |
Experimental details
Crystal data | |
Chemical formula | C19H16N4O |
Mr | 316.36 |
Crystal system, space group | Monoclinic, Cc |
Temperature (K) | 293 |
a, b, c (Å) | 14.0350 (2), 14.4517 (2), 8.1372 (1) |
β (°) | 102.193 (1) |
V (Å3) | 1613.23 (4) |
Z | 4 |
Radiation type | Mo Kα |
µ (mm−1) | 0.08 |
Crystal size (mm) | 0.60 × 0.15 × 0.10 |
Data collection | |
Diffractometer | Bruker APEXII CCD area-detector |
Absorption correction | – |
No. of measured, independent and observed [I > 2σ(I)] reflections | 12370, 2340, 2260 |
Rint | 0.023 |
(sin θ/λ)max (Å−1) | 0.703 |
Refinement | |
R[F2 > 2σ(F2)], wR(F2), S | 0.034, 0.100, 1.17 |
No. of reflections | 2340 |
No. of parameters | 281 |
No. of restraints | 17 |
H-atom treatment | H atoms treated by a mixture of independent and constrained refinement |
Δρmax, Δρmin (e Å−3) | 0.38, −0.26 |
Absolute structure | Friedel pairs were merged |
Computer programs: APEX2 (Bruker, 2005), SAINT (Bruker, 2005), SAINT, SHELXS97 (Sheldrick, 1997), SHELXL97 (Sheldrick, 1997), X-SEED (Barbour, 2001), publCIF (Westrip, 2007).
D—H···A | D—H | H···A | D···A | D—H···A |
N1—H1N···O1i | 0.88 (1) | 1.98 (1) | 2.848 (2) | 174 (3) |
N3—H3N···O1ii | 0.87 (1) | 1.97 (1) | 2.808 (2) | 163 (2) |
Symmetry codes: (i) x+1/2, y−1/2, z; (ii) x, −y+1, z−1/2. |
A previous study reported 2'-[(5-chloro-1H-indol-3-yl)methylene]-2-(1H-indol-3-yl)acetohydrazide, a compound that is N–H···O hydrogen bonded into a three-dimensional network (Ali et al., 2007). Although there are three possible donor sites, the site belonging to the indolyl ring that is linked to the methylene unit is not involved in the H bond interactions. A similar type of hydrogen bonding (Table 1) is found in the unsubstituted title compound, (I), (Fig. 1).