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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

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S2056989022002973/yk2166sup1.cif
Contains datablocks global, I

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S2056989022002973/yk2166Isup2.hkl
Contains datablock I

cml

Chemical Markup Language (CML) file https://doi.org/10.1107/S2056989022002973/yk2166Isup3.cml
Supplementary material

CCDC reference: 2159620

Key indicators

  • Single-crystal X-ray study
  • T = 123 K
  • Mean [sigma](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

Computing details top

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-(1H-Indol-2-ylmethylidene)-4-methoxyaniline top
Crystal data top
C16H14N2OF(000) = 528.00
Mr = 250.29Dx = 1.308 Mg m3
Monoclinic, P21/nMo Kα radiation, λ = 0.71073 Å
a = 5.87685 (19) ÅCell parameters from 6329 reflections
b = 7.5999 (3) Åθ = 2.8–30.8°
c = 28.4578 (11) ŵ = 0.08 mm1
β = 90.604 (3)°T = 123 K
V = 1270.95 (8) Å3Prism, colourless
Z = 40.30 × 0.20 × 0.10 mm
Data collection top
Rigaku AFC10 Saturn70 area detector
diffractometer
2907 independent reflections
Radiation source: rotating anode X-ray generator, micromax0072525 reflections with F2 > 2.0σ(F2)
Multi-layer mirror optics monochromatorRint = 0.056
Detector resolution: 28.5714 pixels mm-1θmax = 27.5°, θmin = 2.8°
ω scansh = 77
Absorption correction: multi-scan
CrysAlisPro; Rigaku OD, 2018)
k = 89
Tmin = 0.608, Tmax = 0.992l = 3635
11128 measured reflections
Refinement top
Refinement on F2Hydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.049H 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 reflectionsΔρmax = 0.39 e Å3
178 parametersΔρmin = 0.29 e Å3
0 restraintsExtinction correction: SHELXL
Primary atom site location: structure-invariant direct methodsExtinction 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
xyzUiso*/Ueq
O10.06455 (16)0.60985 (13)0.93970 (3)0.0292 (3)
N20.57779 (18)0.68608 (14)0.66418 (4)0.0237 (3)
N30.40410 (18)0.64748 (14)0.75724 (4)0.0248 (3)
C40.7005 (2)0.61479 (16)0.70151 (4)0.0240 (3)
C50.9058 (2)0.55340 (17)0.68542 (5)0.0249 (3)
H51.01990.50070.70340.030*
C60.9115 (2)0.58536 (16)0.63609 (4)0.0221 (3)
C71.0717 (2)0.55168 (17)0.60070 (5)0.0253 (3)
H71.20790.49500.60790.030*
C81.0237 (2)0.60388 (17)0.55530 (5)0.0272 (3)
H81.12870.58220.53180.033*
C90.8174 (2)0.68975 (17)0.54398 (5)0.0266 (3)
H90.78990.72500.51310.032*
C100.6548 (2)0.72278 (17)0.57776 (4)0.0253 (3)
H100.51820.77800.57010.030*
C110.7037 (2)0.67011 (16)0.62387 (4)0.0219 (3)
C120.6095 (2)0.60207 (17)0.74822 (4)0.0245 (3)
H120.70190.55990.77240.029*
C130.3193 (2)0.62794 (16)0.80344 (4)0.0231 (3)
C140.4210 (2)0.52631 (17)0.83908 (5)0.0264 (3)
H140.55110.46120.83270.032*
C150.3296 (2)0.52215 (17)0.88355 (5)0.0266 (3)
H150.39930.45480.90690.032*
C160.1332 (2)0.61828 (16)0.89388 (4)0.0233 (3)
C170.0233 (2)0.71292 (17)0.85845 (5)0.0253 (3)
H170.11110.77290.86450.030*
C180.1179 (2)0.71653 (17)0.81370 (5)0.0247 (3)
H180.04460.77980.79000.030*
C190.1427 (3)0.6969 (2)0.95149 (5)0.0367 (4)
H19A0.17930.67220.98360.044*
H19B0.26320.65540.93130.044*
H19C0.12470.82150.94740.044*
H20.438 (3)0.737 (2)0.6678 (5)0.032 (4)*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
O10.0294 (5)0.0304 (5)0.0279 (5)0.0010 (4)0.0024 (4)0.0028 (4)
N20.0196 (5)0.0258 (6)0.0258 (5)0.0019 (4)0.0007 (4)0.0004 (4)
N30.0257 (5)0.0218 (6)0.0270 (6)0.0006 (4)0.0012 (4)0.0001 (4)
C40.0223 (6)0.0226 (6)0.0270 (7)0.0032 (5)0.0028 (5)0.0007 (5)
C50.0216 (6)0.0242 (6)0.0288 (7)0.0008 (5)0.0046 (5)0.0014 (5)
C60.0194 (6)0.0180 (6)0.0289 (7)0.0027 (4)0.0030 (5)0.0015 (5)
C70.0192 (6)0.0228 (6)0.0339 (7)0.0008 (5)0.0006 (5)0.0029 (5)
C80.0247 (6)0.0259 (7)0.0310 (7)0.0034 (5)0.0029 (5)0.0056 (5)
C90.0289 (6)0.0249 (7)0.0258 (6)0.0022 (5)0.0032 (5)0.0005 (5)
C100.0235 (6)0.0238 (6)0.0283 (7)0.0021 (5)0.0040 (5)0.0000 (5)
C110.0194 (6)0.0189 (6)0.0273 (6)0.0015 (5)0.0009 (4)0.0023 (5)
C120.0237 (6)0.0239 (7)0.0259 (6)0.0032 (5)0.0042 (5)0.0007 (5)
C130.0221 (6)0.0200 (6)0.0270 (6)0.0023 (5)0.0017 (5)0.0005 (5)
C140.0216 (6)0.0242 (7)0.0335 (7)0.0047 (5)0.0029 (5)0.0042 (5)
C150.0250 (6)0.0243 (7)0.0305 (7)0.0019 (5)0.0022 (5)0.0053 (5)
C160.0239 (6)0.0192 (6)0.0266 (6)0.0043 (5)0.0009 (5)0.0025 (5)
C170.0206 (6)0.0212 (6)0.0340 (7)0.0012 (5)0.0017 (5)0.0023 (5)
C180.0227 (6)0.0222 (6)0.0289 (7)0.0009 (5)0.0054 (5)0.0016 (5)
C190.0341 (8)0.0398 (9)0.0364 (8)0.0040 (6)0.0069 (6)0.0064 (7)
Geometric parameters (Å, º) top
O1—C161.3705 (15)C9—H90.9300
O1—C191.4287 (17)C10—C111.3989 (17)
N2—C111.3769 (16)C10—H100.9300
N2—C41.3876 (16)C12—H120.9300
N2—H20.912 (17)C13—C181.3950 (17)
N3—C121.2840 (17)C13—C141.4035 (18)
N3—C131.4189 (17)C14—C151.3803 (18)
C4—C51.3768 (18)C14—H140.9300
C4—C121.4413 (18)C15—C161.4000 (18)
C5—C61.4252 (18)C15—H150.9300
C5—H50.9300C16—C171.3918 (18)
C6—C71.4094 (18)C17—C181.3950 (18)
C6—C111.4205 (17)C17—H170.9300
C7—C81.3781 (19)C18—H180.9300
C7—H70.9300C19—H19A0.9600
C8—C91.4111 (18)C19—H19B0.9600
C8—H80.9300C19—H19C0.9600
C9—C101.3852 (19)
C16—O1—C19117.50 (11)C10—C11—C6121.79 (12)
C11—N2—C4108.89 (10)N3—C12—C4121.67 (12)
C11—N2—H2128.4 (10)N3—C12—H12119.2
C4—N2—H2122.7 (10)C4—C12—H12119.2
C12—N3—C13119.83 (11)C18—C13—C14118.05 (12)
C5—C4—N2109.15 (11)C18—C13—N3116.78 (11)
C5—C4—C12128.24 (12)C14—C13—N3125.17 (12)
N2—C4—C12122.51 (11)C15—C14—C13120.54 (12)
C4—C5—C6107.42 (11)C15—C14—H14119.7
C4—C5—H5126.3C13—C14—H14119.7
C6—C5—H5126.3C14—C15—C16120.68 (12)
C7—C6—C11119.10 (12)C14—C15—H15119.7
C7—C6—C5134.07 (12)C16—C15—H15119.7
C11—C6—C5106.83 (11)O1—C16—C17125.06 (12)
C8—C7—C6119.08 (12)O1—C16—C15115.28 (11)
C8—C7—H7120.5C17—C16—C15119.65 (12)
C6—C7—H7120.5C16—C17—C18119.03 (12)
C7—C8—C9120.94 (12)C16—C17—H17120.5
C7—C8—H8119.5C18—C17—H17120.5
C9—C8—H8119.5C13—C18—C17121.91 (11)
C10—C9—C8121.49 (12)C13—C18—H18119.0
C10—C9—H9119.3C17—C18—H18119.0
C8—C9—H9119.3O1—C19—H19A109.5
C9—C10—C11117.58 (12)O1—C19—H19B109.5
C9—C10—H10121.2H19A—C19—H19B109.5
C11—C10—H10121.2O1—C19—H19C109.5
N2—C11—C10130.50 (11)H19A—C19—H19C109.5
N2—C11—C6107.71 (11)H19B—C19—H19C109.5
C11—N2—C4—C50.24 (14)C5—C6—C11—C10179.05 (11)
C11—N2—C4—C12176.34 (11)C13—N3—C12—C4178.13 (11)
N2—C4—C5—C60.69 (14)C5—C4—C12—N3171.94 (13)
C12—C4—C5—C6175.63 (12)N2—C4—C12—N33.94 (19)
C4—C5—C6—C7179.42 (14)C12—N3—C13—C18165.19 (12)
C4—C5—C6—C110.87 (14)C12—N3—C13—C1415.23 (19)
C11—C6—C7—C80.81 (18)C18—C13—C14—C153.23 (19)
C5—C6—C7—C8178.88 (13)N3—C13—C14—C15177.21 (12)
C6—C7—C8—C90.08 (19)C13—C14—C15—C160.4 (2)
C7—C8—C9—C100.8 (2)C19—O1—C16—C173.66 (18)
C8—C9—C10—C110.89 (19)C19—O1—C16—C15176.29 (12)
C4—N2—C11—C10179.44 (13)C14—C15—C16—O1177.25 (11)
C4—N2—C11—C60.32 (14)C14—C15—C16—C172.80 (19)
C9—C10—C11—N2179.59 (12)O1—C16—C17—C18177.07 (11)
C9—C10—C11—C60.14 (19)C15—C16—C17—C182.98 (18)
C7—C6—C11—N2179.51 (11)C14—C13—C18—C173.04 (19)
C5—C6—C11—N20.73 (13)N3—C13—C18—C17177.36 (11)
C7—C6—C11—C100.71 (19)C16—C17—C18—C130.05 (19)
Hydrogen-bond geometry (Å, º) top
Cg1 and Cg2 are the centroids of the N2/C4–C6/C11 and C6–C11 rings, respectively.
D—H···AD—HH···AD···AD—H···A
C10—H10···O1i0.932.583.2479 (16)129
C14—H14···Cg1ii0.932.813.6006 (14)143
C15—H15···Cg2ii0.932.793.5153 (14)136
C17—H17···Cg1i0.932.893.5718 (14)131
C19—H19C···Cg2i0.962.973.7716 (16)142
Symmetry codes: (i) x+1/2, y+1/2, z+3/2; (ii) x+3/2, y1/2, z+3/2.
 

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