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In the title com­pound, the dihedral angle between the planes of the bi­pyridine and carbazole moieties connected by an O atom is 68.45 (3)°. The bi­pyridine ring system, with two meth­oxy substituents, is approximately planar. The pyridine ring in the pyridyl-substituted carbazole fragment is tilted by 56.65 (4)° with respect to the mean plane of the carbazole moiety. The title com­pound exhibits a high energy gap and triplet energy.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S2056989019013549/fy2142sup1.cif
Contains datablocks I, New_Global_Publ_Block

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S2056989019013549/fy2142Isup2.hkl
Contains datablock I

CCDC reference: 1957451

Key indicators

  • Single-crystal X-ray study
  • T = 173 K
  • Mean [sigma](C-C) = 0.003 Å
  • R factor = 0.034
  • wR factor = 0.084
  • Data-to-parameter ratio = 15.8

checkCIF/PLATON results

No syntax errors found



Datablock: I


Alert level C PLAT915_ALERT_3_C No Flack x Check Done: Low Friedel Pair Coverage 82 %
Alert level G PLAT128_ALERT_4_G Alternate Setting for Input Space Group Ia Ic Note PLAT912_ALERT_4_G Missing # of FCF Reflections Above STh/L= 0.600 4 Note PLAT978_ALERT_2_G Number C-C Bonds with Positive Residual Density. 14 Info
0 ALERT level A = Most likely a serious problem - resolve or explain 0 ALERT level B = A potentially serious problem, consider carefully 1 ALERT level C = Check. Ensure it is not caused by an omission or oversight 3 ALERT level G = General information/check it is not something unexpected 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 2 ALERT type 4 Improvement, methodology, query or suggestion 0 ALERT type 5 Informative message, check

Computing details top

Data collection: APEX2 (Bruker, 2014); cell refinement: SAINT (Bruker, 2014); data reduction: SAINT (Bruker, 2014); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL2014 (Sheldrick, 2015); molecular graphics: DIAMOND (Brandenburg, 2010); software used to prepare material for publication: SHELXTL (Sheldrick, 2008) and publCIF (Westrip, 2010).

2-[(2',6'-Dimethoxy-2,3'-bipyridin-6-yl)oxy]-9-(pyridin-2-yl)-9H-carbazole top
Crystal data top
C29H22N4O3F(000) = 992
Mr = 474.50Dx = 1.385 Mg m3
Monoclinic, IaMo Kα radiation, λ = 0.71073 Å
a = 9.6979 (1) ÅCell parameters from 6053 reflections
b = 23.6702 (3) Åθ = 2.2–28.3°
c = 9.9229 (2) ŵ = 0.09 mm1
β = 92.9125 (5)°T = 173 K
V = 2274.87 (6) Å3Block, colourless
Z = 40.53 × 0.46 × 0.12 mm
Data collection top
Bruker APEXII CCD
diffractometer
4943 reflections with I > 2σ(I)
φ and ω scansRint = 0.020
Absorption correction: multi-scan
(SADABS; Bruker, 2014)
θmax = 28.4°, θmin = 1.7°
Tmin = 0.710, Tmax = 0.746h = 1212
10918 measured reflectionsk = 3131
5179 independent reflectionsl = 1312
Refinement top
Refinement on F2Secondary atom site location: difference Fourier map
Least-squares matrix: fullHydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.034H-atom parameters constrained
wR(F2) = 0.084 w = 1/[σ2(Fo2) + (0.0404P)2 + 0.7038P]
where P = (Fo2 + 2Fc2)/3
S = 1.06(Δ/σ)max < 0.001
5179 reflectionsΔρmax = 0.21 e Å3
328 parametersΔρmin = 0.19 e Å3
2 restraintsExtinction correction: SHELXL2014 (Sheldrick, 2015), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
Primary atom site location: structure-invariant direct methodsExtinction coefficient: 0.0062 (6)
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.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
O10.16676 (16)0.24337 (6)0.28067 (15)0.0285 (3)
O20.27313 (17)0.33138 (6)0.70330 (18)0.0382 (4)
O30.43670 (17)0.15756 (6)0.82051 (17)0.0358 (4)
N10.3339 (2)0.06572 (7)0.02064 (19)0.0287 (4)
N20.30895 (18)0.04679 (7)0.24867 (18)0.0270 (4)
N30.00057 (17)0.25161 (7)0.43700 (18)0.0244 (3)
N40.35398 (18)0.24417 (7)0.75714 (19)0.0273 (4)
C10.3152 (3)0.05001 (10)0.1083 (2)0.0344 (5)
H10.35160.07370.17520.041*
C20.2465 (3)0.00167 (10)0.1504 (2)0.0360 (5)
H20.23990.00860.24310.043*
C30.1874 (3)0.03137 (10)0.0545 (3)0.0379 (5)
H30.13780.06460.08010.045*
C40.2016 (3)0.01536 (9)0.0794 (2)0.0353 (5)
H40.15940.03650.14750.042*
C50.2793 (2)0.03247 (8)0.1115 (2)0.0246 (4)
C60.3774 (2)0.01129 (8)0.3428 (2)0.0261 (4)
C70.4216 (2)0.04424 (9)0.3285 (2)0.0305 (4)
H70.40500.06420.24620.037*
C80.4904 (2)0.06934 (9)0.4381 (2)0.0331 (5)
H80.52080.10730.43110.040*
C90.5164 (3)0.04006 (10)0.5592 (2)0.0356 (5)
H90.56330.05840.63330.043*
C100.4742 (2)0.01540 (9)0.5717 (2)0.0319 (5)
H100.49370.03550.65340.038*
C110.4030 (2)0.04161 (8)0.4635 (2)0.0253 (4)
C120.3469 (2)0.09767 (8)0.44159 (19)0.0231 (4)
C130.3371 (2)0.14504 (8)0.5239 (2)0.0259 (4)
H130.37410.14430.61440.031*
C140.2730 (2)0.19313 (8)0.4724 (2)0.0263 (4)
H140.26480.22560.52770.032*
C150.2203 (2)0.19380 (8)0.3386 (2)0.0243 (4)
C160.2283 (2)0.14802 (8)0.2536 (2)0.0240 (4)
H160.19200.14930.16290.029*
C170.2923 (2)0.09974 (8)0.3073 (2)0.0232 (4)
C180.0820 (2)0.27662 (8)0.3548 (2)0.0239 (4)
C190.0883 (2)0.33456 (9)0.3325 (2)0.0309 (5)
H190.14910.35060.27080.037*
C200.0015 (2)0.36732 (9)0.4049 (2)0.0347 (5)
H200.00190.40720.39410.042*
C210.0865 (2)0.34265 (9)0.4935 (2)0.0299 (5)
H210.14610.36530.54400.036*
C220.0865 (2)0.28402 (8)0.5075 (2)0.0238 (4)
C230.1789 (2)0.25192 (8)0.5941 (2)0.0251 (4)
C240.2697 (2)0.27479 (8)0.6851 (2)0.0261 (4)
C250.3517 (2)0.18857 (9)0.7446 (2)0.0301 (4)
C260.2677 (3)0.16054 (10)0.6591 (3)0.0431 (6)
H260.26890.12050.65190.052*
C270.1815 (3)0.19309 (9)0.5844 (3)0.0374 (5)
H270.12220.17490.52450.045*
C280.3786 (3)0.35291 (10)0.7870 (3)0.0458 (6)
H28A0.36130.39300.80610.069*
H28B0.37700.33170.87190.069*
H28C0.46930.34860.73980.069*
C290.5206 (3)0.18868 (10)0.9090 (3)0.0366 (5)
H29A0.57240.16230.96340.055*
H29B0.58540.21250.85550.055*
H29C0.46160.21250.96860.055*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
O10.0366 (8)0.0230 (7)0.0266 (7)0.0077 (6)0.0087 (6)0.0039 (6)
O20.0429 (9)0.0230 (7)0.0510 (10)0.0008 (6)0.0243 (8)0.0039 (7)
O30.0361 (8)0.0275 (8)0.0446 (10)0.0009 (6)0.0100 (8)0.0102 (7)
N10.0347 (9)0.0247 (8)0.0272 (9)0.0012 (7)0.0062 (7)0.0023 (7)
N20.0367 (10)0.0195 (8)0.0249 (9)0.0020 (7)0.0032 (7)0.0003 (6)
N30.0248 (8)0.0212 (8)0.0275 (8)0.0015 (6)0.0032 (7)0.0005 (6)
N40.0247 (9)0.0268 (8)0.0306 (9)0.0009 (7)0.0032 (7)0.0034 (7)
C10.0435 (13)0.0330 (11)0.0272 (11)0.0016 (10)0.0085 (9)0.0003 (9)
C20.0410 (13)0.0362 (12)0.0303 (11)0.0063 (10)0.0024 (10)0.0106 (9)
C30.0409 (13)0.0272 (11)0.0448 (14)0.0027 (9)0.0062 (11)0.0101 (9)
C40.0420 (13)0.0277 (11)0.0364 (12)0.0074 (9)0.0034 (10)0.0005 (9)
C50.0278 (10)0.0206 (9)0.0254 (10)0.0023 (7)0.0025 (8)0.0029 (7)
C60.0282 (10)0.0245 (9)0.0262 (10)0.0008 (8)0.0072 (8)0.0032 (7)
C70.0367 (11)0.0240 (9)0.0314 (11)0.0010 (8)0.0094 (9)0.0002 (8)
C80.0342 (11)0.0248 (10)0.0413 (12)0.0050 (8)0.0116 (9)0.0054 (9)
C90.0386 (12)0.0349 (11)0.0337 (12)0.0095 (9)0.0047 (10)0.0104 (9)
C100.0346 (11)0.0351 (11)0.0265 (10)0.0070 (9)0.0055 (9)0.0045 (8)
C110.0247 (10)0.0254 (9)0.0264 (10)0.0022 (7)0.0078 (8)0.0023 (8)
C120.0227 (9)0.0248 (9)0.0222 (9)0.0009 (7)0.0048 (7)0.0019 (7)
C130.0276 (9)0.0288 (10)0.0215 (9)0.0012 (8)0.0034 (7)0.0012 (8)
C140.0291 (10)0.0236 (9)0.0268 (10)0.0007 (8)0.0064 (8)0.0039 (8)
C150.0238 (9)0.0217 (9)0.0283 (10)0.0009 (7)0.0088 (8)0.0019 (7)
C160.0249 (9)0.0243 (9)0.0231 (9)0.0010 (7)0.0043 (7)0.0006 (7)
C170.0248 (9)0.0220 (9)0.0233 (9)0.0024 (7)0.0058 (8)0.0015 (7)
C180.0256 (9)0.0227 (9)0.0235 (9)0.0039 (8)0.0016 (8)0.0004 (7)
C190.0330 (11)0.0242 (10)0.0364 (12)0.0018 (8)0.0099 (9)0.0067 (8)
C200.0398 (12)0.0203 (9)0.0448 (13)0.0048 (9)0.0109 (10)0.0036 (9)
C210.0297 (10)0.0243 (10)0.0364 (12)0.0059 (8)0.0096 (9)0.0003 (8)
C220.0223 (9)0.0221 (9)0.0269 (10)0.0016 (7)0.0002 (8)0.0006 (7)
C230.0226 (9)0.0228 (9)0.0300 (10)0.0025 (7)0.0018 (8)0.0030 (8)
C240.0246 (9)0.0242 (9)0.0294 (10)0.0011 (7)0.0014 (8)0.0016 (8)
C250.0270 (10)0.0275 (10)0.0359 (11)0.0003 (8)0.0025 (9)0.0070 (9)
C260.0481 (15)0.0218 (10)0.0613 (17)0.0015 (10)0.0208 (13)0.0050 (10)
C270.0407 (12)0.0241 (10)0.0489 (14)0.0037 (9)0.0182 (11)0.0004 (9)
C280.0540 (15)0.0298 (11)0.0565 (16)0.0028 (11)0.0298 (13)0.0055 (11)
C290.0359 (12)0.0377 (12)0.0370 (12)0.0085 (10)0.0090 (10)0.0034 (10)
Geometric parameters (Å, º) top
O1—C181.378 (2)C10—H100.9500
O1—C151.395 (2)C11—C121.446 (3)
O2—C241.352 (2)C12—C131.393 (3)
O2—C281.443 (3)C12—C171.409 (3)
O3—C251.360 (3)C13—C141.383 (3)
O3—C291.431 (3)C13—H130.9500
N1—C51.327 (3)C14—C151.398 (3)
N1—C11.335 (3)C14—H140.9500
N2—C171.395 (2)C15—C161.378 (3)
N2—C61.399 (3)C16—C171.393 (3)
N2—C51.417 (3)C16—H160.9500
N3—C181.312 (3)C18—C191.391 (3)
N3—C221.353 (3)C19—C201.373 (3)
N4—C251.322 (3)C19—H190.9500
N4—C241.328 (3)C20—C211.386 (3)
C1—C21.379 (3)C20—H200.9500
C1—H10.9500C21—C221.395 (3)
C2—C31.379 (4)C21—H210.9500
C2—H20.9500C22—C231.482 (3)
C3—C41.382 (3)C23—C271.396 (3)
C3—H30.9500C23—C241.402 (3)
C4—C51.388 (3)C25—C261.377 (3)
C4—H40.9500C26—C271.380 (3)
C6—C71.392 (3)C26—H260.9500
C6—C111.407 (3)C27—H270.9500
C7—C81.380 (3)C28—H28A0.9800
C7—H70.9500C28—H28B0.9800
C8—C91.399 (3)C28—H28C0.9800
C8—H80.9500C29—H29A0.9800
C9—C101.382 (3)C29—H29B0.9800
C9—H90.9500C29—H29C0.9800
C10—C111.393 (3)
C18—O1—C15118.70 (15)C16—C15—O1116.16 (18)
C24—O2—C28116.72 (17)C16—C15—C14122.88 (18)
C25—O3—C29116.20 (17)O1—C15—C14120.73 (17)
C5—N1—C1116.50 (19)C15—C16—C17116.67 (18)
C17—N2—C6108.79 (16)C15—C16—H16121.7
C17—N2—C5126.41 (16)C17—C16—H16121.7
C6—N2—C5124.30 (16)C16—C17—N2129.49 (18)
C18—N3—C22118.47 (17)C16—C17—C12121.93 (18)
C25—N4—C24118.63 (19)N2—C17—C12108.51 (16)
N1—C1—C2124.2 (2)N3—C18—O1118.27 (17)
N1—C1—H1117.9N3—C18—C19125.21 (19)
C2—C1—H1117.9O1—C18—C19116.49 (19)
C3—C2—C1118.2 (2)C20—C19—C18116.1 (2)
C3—C2—H2120.9C20—C19—H19121.9
C1—C2—H2120.9C18—C19—H19121.9
C2—C3—C4118.9 (2)C19—C20—C21120.5 (2)
C2—C3—H3120.5C19—C20—H20119.7
C4—C3—H3120.5C21—C20—H20119.7
C3—C4—C5118.1 (2)C20—C21—C22119.04 (19)
C3—C4—H4120.9C20—C21—H21120.5
C5—C4—H4120.9C22—C21—H21120.5
N1—C5—C4123.9 (2)N3—C22—C21120.63 (19)
N1—C5—N2116.24 (18)N3—C22—C23114.54 (16)
C4—C5—N2119.80 (19)C21—C22—C23124.80 (18)
C7—C6—N2129.6 (2)C27—C23—C24114.82 (19)
C7—C6—C11121.8 (2)C27—C23—C22118.74 (19)
N2—C6—C11108.61 (17)C24—C23—C22126.41 (18)
C8—C7—C6117.7 (2)N4—C24—O2116.67 (18)
C8—C7—H7121.1N4—C24—C23124.05 (18)
C6—C7—H7121.1O2—C24—C23119.27 (18)
C7—C8—C9121.5 (2)N4—C25—O3118.2 (2)
C7—C8—H8119.3N4—C25—C26123.4 (2)
C9—C8—H8119.3O3—C25—C26118.41 (19)
C10—C9—C8120.4 (2)C25—C26—C27117.1 (2)
C10—C9—H9119.8C25—C26—H26121.4
C8—C9—H9119.8C27—C26—H26121.4
C9—C10—C11119.4 (2)C26—C27—C23121.9 (2)
C9—C10—H10120.3C26—C27—H27119.0
C11—C10—H10120.3C23—C27—H27119.0
C10—C11—C6119.22 (19)O2—C28—H28A109.5
C10—C11—C12133.8 (2)O2—C28—H28B109.5
C6—C11—C12106.95 (17)H28A—C28—H28B109.5
C13—C12—C17119.52 (18)O2—C28—H28C109.5
C13—C12—C11133.37 (18)H28A—C28—H28C109.5
C17—C12—C11107.10 (17)H28B—C28—H28C109.5
C14—C13—C12119.24 (19)O3—C29—H29A109.5
C14—C13—H13120.4O3—C29—H29B109.5
C12—C13—H13120.4H29A—C29—H29B109.5
C13—C14—C15119.76 (18)O3—C29—H29C109.5
C13—C14—H14120.1H29A—C29—H29C109.5
C15—C14—H14120.1H29B—C29—H29C109.5
C5—N1—C1—C21.4 (3)C6—N2—C17—C16178.7 (2)
N1—C1—C2—C33.2 (4)C5—N2—C17—C169.2 (3)
C1—C2—C3—C41.1 (4)C6—N2—C17—C121.7 (2)
C2—C3—C4—C52.3 (4)C5—N2—C17—C12173.88 (18)
C1—N1—C5—C42.4 (3)C13—C12—C17—C160.0 (3)
C1—N1—C5—N2175.06 (19)C11—C12—C17—C16179.17 (18)
C3—C4—C5—N14.3 (3)C13—C12—C17—N2177.21 (18)
C3—C4—C5—N2173.1 (2)C11—C12—C17—N22.0 (2)
C17—N2—C5—N151.1 (3)C22—N3—C18—O1178.41 (17)
C6—N2—C5—N1119.9 (2)C22—N3—C18—C190.6 (3)
C17—N2—C5—C4131.3 (2)C15—O1—C18—N334.5 (3)
C6—N2—C5—C457.7 (3)C15—O1—C18—C19147.49 (19)
C17—N2—C6—C7177.0 (2)N3—C18—C19—C200.9 (3)
C5—N2—C6—C74.6 (3)O1—C18—C19—C20178.79 (19)
C17—N2—C6—C110.8 (2)C18—C19—C20—C210.4 (4)
C5—N2—C6—C11173.16 (18)C19—C20—C21—C220.4 (4)
N2—C6—C7—C8178.5 (2)C18—N3—C22—C210.3 (3)
C11—C6—C7—C81.0 (3)C18—N3—C22—C23178.03 (17)
C6—C7—C8—C90.6 (3)C20—C21—C22—N30.8 (3)
C7—C8—C9—C100.5 (4)C20—C21—C22—C23177.4 (2)
C8—C9—C10—C111.3 (4)N3—C22—C23—C277.2 (3)
C9—C10—C11—C61.0 (3)C21—C22—C23—C27171.1 (2)
C9—C10—C11—C12179.1 (2)N3—C22—C23—C24174.66 (18)
C7—C6—C11—C100.2 (3)C21—C22—C23—C247.0 (3)
N2—C6—C11—C10178.16 (18)C25—N4—C24—O2178.53 (19)
C7—C6—C11—C12178.39 (19)C25—N4—C24—C231.0 (3)
N2—C6—C11—C120.4 (2)C28—O2—C24—N46.9 (3)
C10—C11—C12—C134.2 (4)C28—O2—C24—C23173.6 (2)
C6—C11—C12—C13177.6 (2)C27—C23—C24—N40.6 (3)
C10—C11—C12—C17176.8 (2)C22—C23—C24—N4177.60 (19)
C6—C11—C12—C171.4 (2)C27—C23—C24—O2178.9 (2)
C17—C12—C13—C140.4 (3)C22—C23—C24—O22.9 (3)
C11—C12—C13—C14178.5 (2)C24—N4—C25—O3178.91 (18)
C12—C13—C14—C150.6 (3)C24—N4—C25—C261.0 (4)
C18—O1—C15—C16141.73 (19)C29—O3—C25—N40.6 (3)
C18—O1—C15—C1443.6 (3)C29—O3—C25—C26179.2 (2)
C13—C14—C15—C160.3 (3)N4—C25—C26—C270.5 (4)
C13—C14—C15—O1174.02 (18)O3—C25—C26—C27179.4 (2)
O1—C15—C16—C17174.71 (16)C25—C26—C27—C230.1 (4)
C14—C15—C16—C170.1 (3)C24—C23—C27—C260.1 (4)
C15—C16—C17—N2176.29 (19)C22—C23—C27—C26178.2 (2)
C15—C16—C17—C120.3 (3)
Hydrogen-bond geometry (Å, º) top
Cg1 is the centroid of the C12–C17 ring.
D—H···AD—HH···AD···AD—H···A
C3—H3···O3i0.952.503.429 (3)165
C21—H21···O20.952.202.839 (3)123
C27—H27···N30.952.352.720 (3)102
C29—H29A···N1ii0.982.543.442 (3)154
C8—H8···Cg1iii0.952.763.426 (2)128
C28—H28C···Cg1iv0.982.893.485 (3)120
Symmetry codes: (i) x+1/2, y, z1; (ii) x1, y, z+1; (iii) x+1/2, y, z; (iv) x1, y+1/2, z+1/2.
 

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