The molecule of the title compound contains an essentially planar indole ring system and a phenyl ring. In the crystal, the molecules are linked by a weak intermolecular C—H

O hydrogen bond and C—H

π interactions, forming a two-dimensional network structure.
Supporting information
CCDC reference: 2159620
Key indicators
- Single-crystal X-ray study
- T = 123 K
- Mean
(C-C) = 0.002 Å
- R factor = 0.049
- wR factor = 0.127
- Data-to-parameter ratio = 16.3
checkCIF/PLATON results
No syntax errors found
Alert level C
PLAT420_ALERT_2_C D-H Bond Without Acceptor N2 --H2 . Please Check
| Author Response:
We confirmed that there is no hydrogen bond acceptor for N2--H2.
|
PLAT906_ALERT_3_C Large K Value in the Analysis of Variance ...... 3.149 Check
| Author Response:
K value is large only for weak reflections with Fc/Fc(max) lower than 0.008.
I.e. only the weakest group of reflexes is affected.
We consider that the Alert is not so serious problem.
|
PLAT911_ALERT_3_C Missing FCF Refl Between Thmin & STh/L= 0.600 4 Report
| Author Response:
The completeness of the data collection is 0.998.
The effect of the missing reflections on the refinement of the structure
is therefore negligible.
|
Alert level G
PLAT910_ALERT_3_G Missing # of FCF Reflection(s) Below Theta(Min). 1 Note
PLAT912_ALERT_4_G Missing # of FCF Reflections Above STh/L= 0.600 2 Note
PLAT913_ALERT_3_G Missing # of Very Strong Reflections in FCF .... 1 Note
PLAT978_ALERT_2_G Number C-C Bonds with Positive Residual Density. 10 Info
0 ALERT level A = Most likely a serious problem - resolve or explain
0 ALERT level B = A potentially serious problem, consider carefully
3 ALERT level C = Check. Ensure it is not caused by an omission or oversight
4 ALERT level G = General information/check it is not something unexpected
0 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
2 ALERT type 2 Indicator that the structure model may be wrong or deficient
4 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
Data collection: CrysAlis PRO (Rigaku OD, 2018); cell refinement: CrysAlis PRO (Rigaku OD, 2018); data reduction: CrysAlis PRO (Rigaku OD, 2018); program(s) used to solve structure: SIR92 (Altomare et al., 1993); program(s) used to refine structure: SHELXL2018/3 (Sheldrick, 2015); molecular graphics: PLATON (Spek, 2020); software used to prepare material for publication: CrystalStructure (Rigaku, 2019).
N-(1
H-Indol-2-ylmethylidene)-4-methoxyaniline
top
Crystal data top
C16H14N2O | F(000) = 528.00 |
Mr = 250.29 | Dx = 1.308 Mg m−3 |
Monoclinic, P21/n | Mo Kα radiation, λ = 0.71073 Å |
a = 5.87685 (19) Å | Cell parameters from 6329 reflections |
b = 7.5999 (3) Å | θ = 2.8–30.8° |
c = 28.4578 (11) Å | µ = 0.08 mm−1 |
β = 90.604 (3)° | T = 123 K |
V = 1270.95 (8) Å3 | Prism, colourless |
Z = 4 | 0.30 × 0.20 × 0.10 mm |
Data collection top
Rigaku AFC10 Saturn70 area detector diffractometer | 2907 independent reflections |
Radiation source: rotating anode X-ray generator, micromax007 | 2525 reflections with F2 > 2.0σ(F2) |
Multi-layer mirror optics monochromator | Rint = 0.056 |
Detector resolution: 28.5714 pixels mm-1 | θmax = 27.5°, θmin = 2.8° |
ω scans | h = −7→7 |
Absorption correction: multi-scan CrysAlisPro; Rigaku OD, 2018) | k = −8→9 |
Tmin = 0.608, Tmax = 0.992 | l = −36→35 |
11128 measured reflections | |
Refinement top
Refinement on F2 | Hydrogen site location: inferred from neighbouring sites |
R[F2 > 2σ(F2)] = 0.049 | H atoms treated by a mixture of independent and constrained refinement |
wR(F2) = 0.127 | w = 1/[σ2(Fo2) + (0.0686P)2 + 0.3253P] where P = (Fo2 + 2Fc2)/3 |
S = 1.05 | (Δ/σ)max = 0.001 |
2907 reflections | Δρmax = 0.39 e Å−3 |
178 parameters | Δρmin = −0.29 e Å−3 |
0 restraints | Extinction correction: SHELXL |
Primary atom site location: structure-invariant direct methods | Extinction coefficient: 0.259 (14) |
Secondary atom site location: difference Fourier map | |
Special details top
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 was performed using all reflections. The weighted
R-factor (wR) and goodness of fit (S) are based on F2.
R-factor (gt) are based on F. The threshold expression of
F2 > 2.0 sigma(F2) is used only for calculating R-factor (gt). |
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top | x | y | z | Uiso*/Ueq | |
O1 | 0.06455 (16) | 0.60985 (13) | 0.93970 (3) | 0.0292 (3) | |
N2 | 0.57779 (18) | 0.68608 (14) | 0.66418 (4) | 0.0237 (3) | |
N3 | 0.40410 (18) | 0.64748 (14) | 0.75724 (4) | 0.0248 (3) | |
C4 | 0.7005 (2) | 0.61479 (16) | 0.70151 (4) | 0.0240 (3) | |
C5 | 0.9058 (2) | 0.55340 (17) | 0.68542 (5) | 0.0249 (3) | |
H5 | 1.0199 | 0.5007 | 0.7034 | 0.030* | |
C6 | 0.9115 (2) | 0.58536 (16) | 0.63609 (4) | 0.0221 (3) | |
C7 | 1.0717 (2) | 0.55168 (17) | 0.60070 (5) | 0.0253 (3) | |
H7 | 1.2079 | 0.4950 | 0.6079 | 0.030* | |
C8 | 1.0237 (2) | 0.60388 (17) | 0.55530 (5) | 0.0272 (3) | |
H8 | 1.1287 | 0.5822 | 0.5318 | 0.033* | |
C9 | 0.8174 (2) | 0.68975 (17) | 0.54398 (5) | 0.0266 (3) | |
H9 | 0.7899 | 0.7250 | 0.5131 | 0.032* | |
C10 | 0.6548 (2) | 0.72278 (17) | 0.57776 (4) | 0.0253 (3) | |
H10 | 0.5182 | 0.7780 | 0.5701 | 0.030* | |
C11 | 0.7037 (2) | 0.67011 (16) | 0.62387 (4) | 0.0219 (3) | |
C12 | 0.6095 (2) | 0.60207 (17) | 0.74822 (4) | 0.0245 (3) | |
H12 | 0.7019 | 0.5599 | 0.7724 | 0.029* | |
C13 | 0.3193 (2) | 0.62794 (16) | 0.80344 (4) | 0.0231 (3) | |
C14 | 0.4210 (2) | 0.52631 (17) | 0.83908 (5) | 0.0264 (3) | |
H14 | 0.5511 | 0.4612 | 0.8327 | 0.032* | |
C15 | 0.3296 (2) | 0.52215 (17) | 0.88355 (5) | 0.0266 (3) | |
H15 | 0.3993 | 0.4548 | 0.9069 | 0.032* | |
C16 | 0.1332 (2) | 0.61828 (16) | 0.89388 (4) | 0.0233 (3) | |
C17 | 0.0233 (2) | 0.71292 (17) | 0.85845 (5) | 0.0253 (3) | |
H17 | −0.1111 | 0.7729 | 0.8645 | 0.030* | |
C18 | 0.1179 (2) | 0.71653 (17) | 0.81370 (5) | 0.0247 (3) | |
H18 | 0.0446 | 0.7798 | 0.7900 | 0.030* | |
C19 | −0.1427 (3) | 0.6969 (2) | 0.95149 (5) | 0.0367 (4) | |
H19A | −0.1793 | 0.6722 | 0.9836 | 0.044* | |
H19B | −0.2632 | 0.6554 | 0.9313 | 0.044* | |
H19C | −0.1247 | 0.8215 | 0.9474 | 0.044* | |
H2 | 0.438 (3) | 0.737 (2) | 0.6678 (5) | 0.032 (4)* | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
O1 | 0.0294 (5) | 0.0304 (5) | 0.0279 (5) | 0.0010 (4) | 0.0024 (4) | −0.0028 (4) |
N2 | 0.0196 (5) | 0.0258 (6) | 0.0258 (5) | 0.0019 (4) | −0.0007 (4) | −0.0004 (4) |
N3 | 0.0257 (5) | 0.0218 (6) | 0.0270 (6) | −0.0006 (4) | −0.0012 (4) | 0.0001 (4) |
C4 | 0.0223 (6) | 0.0226 (6) | 0.0270 (7) | −0.0032 (5) | −0.0028 (5) | −0.0007 (5) |
C5 | 0.0216 (6) | 0.0242 (6) | 0.0288 (7) | −0.0008 (5) | −0.0046 (5) | 0.0014 (5) |
C6 | 0.0194 (6) | 0.0180 (6) | 0.0289 (7) | −0.0027 (4) | −0.0030 (5) | −0.0015 (5) |
C7 | 0.0192 (6) | 0.0228 (6) | 0.0339 (7) | 0.0008 (5) | −0.0006 (5) | −0.0029 (5) |
C8 | 0.0247 (6) | 0.0259 (7) | 0.0310 (7) | −0.0034 (5) | 0.0029 (5) | −0.0056 (5) |
C9 | 0.0289 (6) | 0.0249 (7) | 0.0258 (6) | −0.0022 (5) | −0.0032 (5) | −0.0005 (5) |
C10 | 0.0235 (6) | 0.0238 (6) | 0.0283 (7) | 0.0021 (5) | −0.0040 (5) | 0.0000 (5) |
C11 | 0.0194 (6) | 0.0189 (6) | 0.0273 (6) | −0.0015 (5) | −0.0009 (4) | −0.0023 (5) |
C12 | 0.0237 (6) | 0.0239 (7) | 0.0259 (6) | −0.0032 (5) | −0.0042 (5) | −0.0007 (5) |
C13 | 0.0221 (6) | 0.0200 (6) | 0.0270 (6) | −0.0023 (5) | −0.0017 (5) | −0.0005 (5) |
C14 | 0.0216 (6) | 0.0242 (7) | 0.0335 (7) | 0.0047 (5) | 0.0029 (5) | 0.0042 (5) |
C15 | 0.0250 (6) | 0.0243 (7) | 0.0305 (7) | 0.0019 (5) | −0.0022 (5) | 0.0053 (5) |
C16 | 0.0239 (6) | 0.0192 (6) | 0.0266 (6) | −0.0043 (5) | −0.0009 (5) | −0.0025 (5) |
C17 | 0.0206 (6) | 0.0212 (6) | 0.0340 (7) | 0.0012 (5) | −0.0017 (5) | −0.0023 (5) |
C18 | 0.0227 (6) | 0.0222 (6) | 0.0289 (7) | 0.0009 (5) | −0.0054 (5) | 0.0016 (5) |
C19 | 0.0341 (8) | 0.0398 (9) | 0.0364 (8) | 0.0040 (6) | 0.0069 (6) | −0.0064 (7) |
Geometric parameters (Å, º) top
O1—C16 | 1.3705 (15) | C9—H9 | 0.9300 |
O1—C19 | 1.4287 (17) | C10—C11 | 1.3989 (17) |
N2—C11 | 1.3769 (16) | C10—H10 | 0.9300 |
N2—C4 | 1.3876 (16) | C12—H12 | 0.9300 |
N2—H2 | 0.912 (17) | C13—C18 | 1.3950 (17) |
N3—C12 | 1.2840 (17) | C13—C14 | 1.4035 (18) |
N3—C13 | 1.4189 (17) | C14—C15 | 1.3803 (18) |
C4—C5 | 1.3768 (18) | C14—H14 | 0.9300 |
C4—C12 | 1.4413 (18) | C15—C16 | 1.4000 (18) |
C5—C6 | 1.4252 (18) | C15—H15 | 0.9300 |
C5—H5 | 0.9300 | C16—C17 | 1.3918 (18) |
C6—C7 | 1.4094 (18) | C17—C18 | 1.3950 (18) |
C6—C11 | 1.4205 (17) | C17—H17 | 0.9300 |
C7—C8 | 1.3781 (19) | C18—H18 | 0.9300 |
C7—H7 | 0.9300 | C19—H19A | 0.9600 |
C8—C9 | 1.4111 (18) | C19—H19B | 0.9600 |
C8—H8 | 0.9300 | C19—H19C | 0.9600 |
C9—C10 | 1.3852 (19) | | |
| | | |
C16—O1—C19 | 117.50 (11) | C10—C11—C6 | 121.79 (12) |
C11—N2—C4 | 108.89 (10) | N3—C12—C4 | 121.67 (12) |
C11—N2—H2 | 128.4 (10) | N3—C12—H12 | 119.2 |
C4—N2—H2 | 122.7 (10) | C4—C12—H12 | 119.2 |
C12—N3—C13 | 119.83 (11) | C18—C13—C14 | 118.05 (12) |
C5—C4—N2 | 109.15 (11) | C18—C13—N3 | 116.78 (11) |
C5—C4—C12 | 128.24 (12) | C14—C13—N3 | 125.17 (12) |
N2—C4—C12 | 122.51 (11) | C15—C14—C13 | 120.54 (12) |
C4—C5—C6 | 107.42 (11) | C15—C14—H14 | 119.7 |
C4—C5—H5 | 126.3 | C13—C14—H14 | 119.7 |
C6—C5—H5 | 126.3 | C14—C15—C16 | 120.68 (12) |
C7—C6—C11 | 119.10 (12) | C14—C15—H15 | 119.7 |
C7—C6—C5 | 134.07 (12) | C16—C15—H15 | 119.7 |
C11—C6—C5 | 106.83 (11) | O1—C16—C17 | 125.06 (12) |
C8—C7—C6 | 119.08 (12) | O1—C16—C15 | 115.28 (11) |
C8—C7—H7 | 120.5 | C17—C16—C15 | 119.65 (12) |
C6—C7—H7 | 120.5 | C16—C17—C18 | 119.03 (12) |
C7—C8—C9 | 120.94 (12) | C16—C17—H17 | 120.5 |
C7—C8—H8 | 119.5 | C18—C17—H17 | 120.5 |
C9—C8—H8 | 119.5 | C13—C18—C17 | 121.91 (11) |
C10—C9—C8 | 121.49 (12) | C13—C18—H18 | 119.0 |
C10—C9—H9 | 119.3 | C17—C18—H18 | 119.0 |
C8—C9—H9 | 119.3 | O1—C19—H19A | 109.5 |
C9—C10—C11 | 117.58 (12) | O1—C19—H19B | 109.5 |
C9—C10—H10 | 121.2 | H19A—C19—H19B | 109.5 |
C11—C10—H10 | 121.2 | O1—C19—H19C | 109.5 |
N2—C11—C10 | 130.50 (11) | H19A—C19—H19C | 109.5 |
N2—C11—C6 | 107.71 (11) | H19B—C19—H19C | 109.5 |
| | | |
C11—N2—C4—C5 | 0.24 (14) | C5—C6—C11—C10 | 179.05 (11) |
C11—N2—C4—C12 | −176.34 (11) | C13—N3—C12—C4 | 178.13 (11) |
N2—C4—C5—C6 | −0.69 (14) | C5—C4—C12—N3 | −171.94 (13) |
C12—C4—C5—C6 | 175.63 (12) | N2—C4—C12—N3 | 3.94 (19) |
C4—C5—C6—C7 | −179.42 (14) | C12—N3—C13—C18 | 165.19 (12) |
C4—C5—C6—C11 | 0.87 (14) | C12—N3—C13—C14 | −15.23 (19) |
C11—C6—C7—C8 | 0.81 (18) | C18—C13—C14—C15 | −3.23 (19) |
C5—C6—C7—C8 | −178.88 (13) | N3—C13—C14—C15 | 177.21 (12) |
C6—C7—C8—C9 | −0.08 (19) | C13—C14—C15—C16 | 0.4 (2) |
C7—C8—C9—C10 | −0.8 (2) | C19—O1—C16—C17 | 3.66 (18) |
C8—C9—C10—C11 | 0.89 (19) | C19—O1—C16—C15 | −176.29 (12) |
C4—N2—C11—C10 | −179.44 (13) | C14—C15—C16—O1 | −177.25 (11) |
C4—N2—C11—C6 | 0.32 (14) | C14—C15—C16—C17 | 2.80 (19) |
C9—C10—C11—N2 | 179.59 (12) | O1—C16—C17—C18 | 177.07 (11) |
C9—C10—C11—C6 | −0.14 (19) | C15—C16—C17—C18 | −2.98 (18) |
C7—C6—C11—N2 | 179.51 (11) | C14—C13—C18—C17 | 3.04 (19) |
C5—C6—C11—N2 | −0.73 (13) | N3—C13—C18—C17 | −177.36 (11) |
C7—C6—C11—C10 | −0.71 (19) | C16—C17—C18—C13 | 0.05 (19) |
Hydrogen-bond geometry (Å, º) topCg1 and Cg2 are the centroids of the
N2/C4–C6/C11 and C6–C11 rings, respectively. |
D—H···A | D—H | H···A | D···A | D—H···A |
C10—H10···O1i | 0.93 | 2.58 | 3.2479 (16) | 129 |
C14—H14···Cg1ii | 0.93 | 2.81 | 3.6006 (14) | 143 |
C15—H15···Cg2ii | 0.93 | 2.79 | 3.5153 (14) | 136 |
C17—H17···Cg1i | 0.93 | 2.89 | 3.5718 (14) | 131 |
C19—H19C···Cg2i | 0.96 | 2.97 | 3.7716 (16) | 142 |
Symmetry codes: (i) −x+1/2, y+1/2, −z+3/2; (ii) −x+3/2, y−1/2, −z+3/2. |