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In the title mol­ecule, C33H28N2, the pyridine ring forms dihedral angles of 9.7 (1) and 13.0 (1)° with the two attached phenyl rings. The short distance of 3.585 (3) Å between the centroids of the pyridine rings of two neighbouring mol­ecules reveals the existence of π–π inter­actions in the crystal structure.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536806036841/cv2120sup1.cif
Contains datablocks I, global

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536806036841/cv2120Isup2.hkl
Contains datablock I

CCDC reference: 624194

Key indicators

  • Single-crystal X-ray study
  • T = 298 K
  • Mean [sigma](C-C) = 0.005 Å
  • R factor = 0.060
  • wR factor = 0.208
  • Data-to-parameter ratio = 13.7

checkCIF/PLATON results

No syntax errors found



Alert level B PLAT031_ALERT_4_B Refined Extinction Parameter within Range ...... 1.77 Sigma
Alert level C PLAT026_ALERT_3_C Ratio Observed / Unique Reflections too Low .... 48 Perc. PLAT066_ALERT_1_C Predicted and Reported Transmissions Identical . ? PLAT125_ALERT_4_C No _symmetry_space_group_name_Hall Given ....... ? PLAT340_ALERT_3_C Low Bond Precision on C-C bonds (x 1000) Ang ... 5
0 ALERT level A = In general: serious problem 1 ALERT level B = Potentially serious problem 4 ALERT level C = Check and explain 0 ALERT level G = General alerts; check 1 ALERT type 1 CIF construction/syntax error, inconsistent or missing data 0 ALERT type 2 Indicator that the structure model may be wrong or deficient 2 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: SMART (Bruker, 1997); cell refinement: SMART; data reduction: SAINT (Bruker, 1997); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997a); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997a); molecular graphics: SHELXTL (Sheldrick, 1997b); software used to prepare material for publication: SHELXTL.

9-Butyl-3-(2,6-diphenylpyridin-4-yl)-9H-carbazole top
Crystal data top
C33H28N2F(000) = 960
Mr = 452.57Dx = 1.220 Mg m3
Monoclinic, P21/cMo Kα radiation, λ = 0.71073 Å
a = 11.489 (3) ÅCell parameters from 1488 reflections
b = 15.221 (4) Åθ = 2.3–19.9°
c = 15.099 (4) ŵ = 0.07 mm1
β = 111.104 (4)°T = 298 K
V = 2463.1 (11) Å3Block, pale yellow
Z = 40.45 × 0.39 × 0.36 mm
Data collection top
Bruker SMART CCD area-detector
diffractometer
4345 independent reflections
Radiation source: fine-focus sealed tube2082 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.073
φ and ω scansθmax = 25.0°, θmin = 1.9°
Absorption correction: multi-scan
(SADABS; Sheldrick, 1996)
h = 813
Tmin = 0.969, Tmax = 0.975k = 1518
12777 measured reflectionsl = 1717
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)] = 0.060H-atom parameters constrained
wR(F2) = 0.208 w = 1/[σ2(Fo2) + (0.0001P)2]
where P = (Fo2 + 2Fc2)/3
S = 1.04(Δ/σ)max < 0.001
4345 reflectionsΔρmax = 0.19 e Å3
317 parametersΔρmin = 0.18 e Å3
0 restraintsExtinction correction: SHELXL97, Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
Primary atom site location: structure-invariant direct methodsExtinction coefficient: 0.0023 (13)
Special details top

Geometry. All e.s.d.'s (except the e.s.d. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell e.s.d.'s are taken into account individually in the estimation of e.s.d.'s in distances, angles and torsion angles; correlations between e.s.d.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell e.s.d.'s is used for estimating e.s.d.'s involving l.s. planes.

Refinement. Refinement of F2 against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F2, conventional R-factors R are based on F, with F set to zero for negative F2. The threshold expression of F2 > σ(F2) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F2 are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
N10.0176 (2)0.09281 (17)0.55965 (18)0.0547 (7)
N20.6183 (2)0.12518 (16)1.05856 (17)0.0518 (7)
C10.0805 (3)0.0874 (2)0.6457 (2)0.0511 (8)
C20.0844 (3)0.0476 (2)0.7286 (2)0.0574 (9)
H20.01470.01890.73210.069*
C30.1930 (3)0.0513 (2)0.8059 (2)0.0542 (9)
H30.19630.02460.86210.065*
C40.3002 (3)0.09444 (19)0.8028 (2)0.0470 (8)
C50.2960 (3)0.13091 (19)0.7179 (2)0.0476 (8)
H50.36660.15770.71370.057*
C60.1862 (3)0.12756 (19)0.6383 (2)0.0465 (8)
C70.1508 (3)0.1578 (2)0.5414 (2)0.0472 (8)
C80.2148 (3)0.1973 (2)0.4892 (2)0.0570 (9)
H80.29860.21190.51840.068*
C90.1537 (3)0.2145 (2)0.3945 (2)0.0648 (10)
H90.19590.24080.35920.078*
C100.0279 (4)0.1924 (2)0.3514 (2)0.0706 (11)
H100.01270.20520.28730.085*
C110.0378 (3)0.1528 (2)0.3999 (2)0.0629 (10)
H110.12140.13810.36980.075*
C120.0245 (3)0.1350 (2)0.4960 (2)0.0504 (8)
C130.1428 (3)0.0575 (2)0.5420 (2)0.0609 (10)
H13A0.13470.00040.57030.073*
H13B0.18560.05090.47410.073*
C140.2213 (3)0.1135 (2)0.5804 (2)0.0606 (10)
H14A0.24150.16800.54500.073*
H14B0.17400.12780.64620.073*
C150.3403 (3)0.0677 (3)0.5742 (3)0.0754 (11)
H15A0.38650.05350.50810.091*
H15B0.31890.01280.60880.091*
C160.4242 (4)0.1185 (3)0.6116 (3)0.1046 (15)
H16A0.49680.08400.60500.157*
H16B0.44900.17210.57630.157*
H16C0.38050.13190.67740.157*
C170.6333 (3)0.11582 (19)0.9753 (2)0.0484 (8)
C180.5321 (3)0.10512 (19)0.8904 (2)0.0495 (8)
H180.54560.09950.83350.059*
C190.4111 (3)0.10288 (18)0.8904 (2)0.0456 (8)
C200.3993 (3)0.11084 (19)0.9778 (2)0.0521 (8)
H200.32020.10860.98130.062*
C210.5022 (3)0.12209 (19)1.0604 (2)0.0487 (8)
C220.4906 (3)0.1336 (2)1.1543 (2)0.0529 (9)
C230.3800 (4)0.1177 (2)1.1686 (2)0.0701 (11)
H230.31130.09721.11830.084*
C240.3693 (4)0.1314 (3)1.2555 (3)0.0830 (12)
H240.29390.12011.26320.100*
C250.4681 (4)0.1613 (3)1.3301 (3)0.0826 (12)
H250.46030.17111.38850.099*
C260.5795 (4)0.1770 (3)1.3186 (3)0.0875 (13)
H260.64760.19721.36950.105*
C270.5905 (3)0.1629 (2)1.2315 (2)0.0728 (11)
H270.66670.17331.22470.087*
C280.7645 (3)0.1183 (2)0.9795 (2)0.0525 (9)
C290.7957 (3)0.0969 (2)0.9019 (3)0.0734 (11)
H290.73320.08100.84520.088*
C300.9184 (4)0.0990 (3)0.9071 (3)0.0855 (13)
H300.93750.08450.85410.103*
C311.0116 (4)0.1222 (3)0.9898 (3)0.0854 (13)
H311.09410.12360.99340.103*
C320.9823 (4)0.1432 (3)1.0668 (3)0.0815 (12)
H321.04510.15891.12350.098*
C330.8599 (3)0.1414 (2)1.0613 (2)0.0671 (10)
H330.84160.15631.11460.080*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
N10.0394 (16)0.0720 (19)0.0477 (17)0.0068 (14)0.0098 (14)0.0075 (13)
N20.0438 (17)0.0591 (17)0.0493 (17)0.0020 (13)0.0130 (14)0.0016 (12)
C10.043 (2)0.061 (2)0.048 (2)0.0030 (16)0.0142 (17)0.0062 (16)
C20.047 (2)0.069 (2)0.057 (2)0.0073 (17)0.0192 (18)0.0021 (17)
C30.047 (2)0.066 (2)0.048 (2)0.0036 (17)0.0159 (17)0.0016 (16)
C40.041 (2)0.053 (2)0.0457 (19)0.0002 (15)0.0145 (16)0.0031 (15)
C50.0397 (19)0.058 (2)0.047 (2)0.0015 (15)0.0176 (16)0.0052 (15)
C60.0424 (19)0.055 (2)0.0414 (19)0.0008 (15)0.0137 (16)0.0046 (14)
C70.0440 (19)0.0511 (19)0.0460 (19)0.0008 (16)0.0155 (16)0.0070 (15)
C80.050 (2)0.071 (2)0.050 (2)0.0012 (17)0.0187 (17)0.0023 (17)
C90.065 (2)0.075 (2)0.056 (2)0.002 (2)0.022 (2)0.0005 (18)
C100.071 (3)0.089 (3)0.046 (2)0.001 (2)0.014 (2)0.0040 (18)
C110.048 (2)0.081 (3)0.050 (2)0.0054 (19)0.0053 (18)0.0098 (18)
C120.043 (2)0.058 (2)0.047 (2)0.0019 (16)0.0140 (17)0.0046 (16)
C130.0399 (19)0.073 (2)0.066 (2)0.0114 (18)0.0151 (17)0.0147 (18)
C140.047 (2)0.071 (2)0.062 (2)0.0009 (18)0.0173 (18)0.0031 (17)
C150.057 (2)0.084 (3)0.093 (3)0.004 (2)0.036 (2)0.000 (2)
C160.078 (3)0.134 (4)0.114 (4)0.006 (3)0.050 (3)0.020 (3)
C170.045 (2)0.054 (2)0.045 (2)0.0031 (15)0.0141 (17)0.0049 (15)
C180.049 (2)0.058 (2)0.0435 (19)0.0034 (16)0.0189 (17)0.0009 (15)
C190.0453 (19)0.0478 (19)0.0448 (19)0.0044 (15)0.0174 (16)0.0012 (14)
C200.044 (2)0.058 (2)0.053 (2)0.0014 (16)0.0165 (17)0.0014 (15)
C210.042 (2)0.0514 (19)0.049 (2)0.0034 (16)0.0122 (17)0.0010 (14)
C220.052 (2)0.061 (2)0.0422 (19)0.0065 (17)0.0128 (17)0.0038 (15)
C230.067 (3)0.094 (3)0.052 (2)0.001 (2)0.023 (2)0.0004 (19)
C240.084 (3)0.112 (3)0.062 (3)0.007 (3)0.036 (2)0.009 (2)
C250.094 (3)0.101 (3)0.055 (3)0.028 (3)0.030 (3)0.009 (2)
C260.087 (3)0.115 (4)0.049 (3)0.015 (3)0.011 (2)0.004 (2)
C270.062 (2)0.098 (3)0.050 (2)0.008 (2)0.011 (2)0.004 (2)
C280.045 (2)0.057 (2)0.055 (2)0.0013 (16)0.0181 (18)0.0068 (16)
C290.053 (2)0.105 (3)0.065 (2)0.004 (2)0.024 (2)0.001 (2)
C300.064 (3)0.117 (4)0.088 (3)0.008 (3)0.043 (3)0.008 (3)
C310.051 (3)0.100 (3)0.112 (4)0.002 (2)0.037 (3)0.023 (3)
C320.046 (2)0.099 (3)0.092 (3)0.012 (2)0.015 (2)0.011 (2)
C330.047 (2)0.086 (3)0.064 (2)0.009 (2)0.014 (2)0.0011 (19)
Geometric parameters (Å, º) top
N1—C121.380 (4)C15—H15B0.9700
N1—C11.382 (4)C16—H16A0.9600
N1—C131.466 (4)C16—H16B0.9600
N2—C171.337 (4)C16—H16C0.9600
N2—C211.346 (4)C17—C181.395 (4)
C1—C21.377 (4)C17—C281.486 (4)
C1—C61.399 (4)C18—C191.391 (4)
C2—C31.369 (4)C18—H180.9300
C2—H20.9300C19—C201.378 (4)
C3—C41.411 (4)C20—C211.386 (4)
C3—H30.9300C20—H200.9300
C4—C51.382 (4)C21—C221.481 (4)
C4—C191.475 (4)C22—C271.383 (4)
C5—C61.395 (4)C22—C231.385 (5)
C5—H50.9300C23—C241.378 (5)
C6—C71.446 (4)C23—H230.9300
C7—C81.393 (4)C24—C251.358 (5)
C7—C121.407 (4)C24—H240.9300
C8—C91.373 (4)C25—C261.373 (5)
C8—H80.9300C25—H250.9300
C9—C101.396 (5)C26—C271.382 (5)
C9—H90.9300C26—H260.9300
C10—C111.368 (5)C27—H270.9300
C10—H100.9300C28—C331.370 (4)
C11—C121.393 (4)C28—C291.382 (5)
C11—H110.9300C29—C301.383 (5)
C13—C141.501 (4)C29—H290.9300
C13—H13A0.9700C30—C311.367 (5)
C13—H13B0.9700C30—H300.9300
C14—C151.506 (4)C31—C321.360 (5)
C14—H14A0.9700C31—H310.9300
C14—H14B0.9700C32—C331.379 (5)
C15—C161.495 (5)C32—H320.9300
C15—H15A0.9700C33—H330.9300
C12—N1—C1108.1 (3)C15—C16—H16A109.5
C12—N1—C13127.6 (3)C15—C16—H16B109.5
C1—N1—C13124.3 (3)H16A—C16—H16B109.5
C17—N2—C21118.7 (3)C15—C16—H16C109.5
C2—C1—N1129.0 (3)H16A—C16—H16C109.5
C2—C1—C6121.3 (3)H16B—C16—H16C109.5
N1—C1—C6109.7 (3)N2—C17—C18122.0 (3)
C3—C2—C1118.6 (3)N2—C17—C28115.4 (3)
C3—C2—H2120.7C18—C17—C28122.6 (3)
C1—C2—H2120.7C19—C18—C17120.3 (3)
C2—C3—C4122.0 (3)C19—C18—H18119.8
C2—C3—H3119.0C17—C18—H18119.8
C4—C3—H3119.0C20—C19—C18116.1 (3)
C5—C4—C3118.6 (3)C20—C19—C4121.0 (3)
C5—C4—C19121.8 (3)C18—C19—C4122.8 (3)
C3—C4—C19119.5 (3)C19—C20—C21121.8 (3)
C4—C5—C6120.2 (3)C19—C20—H20119.1
C4—C5—H5119.9C21—C20—H20119.1
C6—C5—H5119.9N2—C21—C20121.0 (3)
C5—C6—C1119.3 (3)N2—C21—C22116.6 (3)
C5—C6—C7134.2 (3)C20—C21—C22122.4 (3)
C1—C6—C7106.5 (3)C27—C22—C23117.1 (3)
C8—C7—C12119.6 (3)C27—C22—C21120.7 (3)
C8—C7—C6134.1 (3)C23—C22—C21122.1 (3)
C12—C7—C6106.2 (3)C24—C23—C22121.5 (4)
C9—C8—C7119.7 (3)C24—C23—H23119.2
C9—C8—H8120.1C22—C23—H23119.2
C7—C8—H8120.1C25—C24—C23120.5 (4)
C8—C9—C10119.7 (3)C25—C24—H24119.8
C8—C9—H9120.2C23—C24—H24119.8
C10—C9—H9120.2C24—C25—C26119.5 (4)
C11—C10—C9122.4 (3)C24—C25—H25120.3
C11—C10—H10118.8C26—C25—H25120.3
C9—C10—H10118.8C25—C26—C27120.2 (4)
C10—C11—C12117.9 (3)C25—C26—H26119.9
C10—C11—H11121.0C27—C26—H26119.9
C12—C11—H11121.0C26—C27—C22121.3 (4)
N1—C12—C11129.6 (3)C26—C27—H27119.4
N1—C12—C7109.5 (3)C22—C27—H27119.4
C11—C12—C7120.8 (3)C33—C28—C29117.2 (3)
N1—C13—C14114.2 (3)C33—C28—C17121.0 (3)
N1—C13—H13A108.7C29—C28—C17121.8 (3)
C14—C13—H13A108.7C28—C29—C30121.1 (4)
N1—C13—H13B108.7C28—C29—H29119.4
C14—C13—H13B108.7C30—C29—H29119.4
H13A—C13—H13B107.6C31—C30—C29120.4 (4)
C13—C14—C15111.9 (3)C31—C30—H30119.8
C13—C14—H14A109.2C29—C30—H30119.8
C15—C14—H14A109.2C32—C31—C30119.2 (4)
C13—C14—H14B109.2C32—C31—H31120.4
C15—C14—H14B109.2C30—C31—H31120.4
H14A—C14—H14B107.9C31—C32—C33120.3 (4)
C16—C15—C14115.5 (4)C31—C32—H32119.8
C16—C15—H15A108.4C33—C32—H32119.8
C14—C15—H15A108.4C28—C33—C32121.8 (4)
C16—C15—H15B108.4C28—C33—H33119.1
C14—C15—H15B108.4C32—C33—H33119.1
H15A—C15—H15B107.5
 

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