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In the title compound, C21H19N, the carbazole ring system is essentially planar. The structure is stabilized by both π–π and C—H...π inter­actions. The ethyl­benzene ring was found to be disordered.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536805040195/sj6166sup1.cif
Contains datablocks global, I

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536805040195/sj6166Isup2.hkl
Contains datablock I

CCDC reference: 296726

Key indicators

  • Single-crystal X-ray study
  • T = 294 K
  • Mean [sigma](C-C) = 0.006 Å
  • Disorder in main residue
  • R factor = 0.045
  • wR factor = 0.129
  • Data-to-parameter ratio = 7.6

checkCIF/PLATON results

No syntax errors found



Alert level B PLAT301_ALERT_3_B Main Residue Disorder ......................... 27.00 Perc.
Alert level C PLAT089_ALERT_3_C Poor Data / Parameter Ratio (Zmax .LT. 18) ..... 7.56 PLAT152_ALERT_1_C Supplied and Calc Volume s.u. Inconsistent ..... ? PLAT220_ALERT_2_C Large Non-Solvent C Ueq(max)/Ueq(min) ... 3.43 Ratio PLAT222_ALERT_3_C Large Non-Solvent H Ueq(max)/Ueq(min) ... 3.94 Ratio PLAT242_ALERT_2_C Check Low Ueq as Compared to Neighbors for C17' PLAT340_ALERT_3_C Low Bond Precision on C-C bonds (x 1000) Ang ... 6 PLAT779_ALERT_2_C Suspect or Irrelevant (Bond) Angle in CIF ...... 4.70 Deg. C14 -C13 -C14' 1.555 1.555 1.555
Alert level G REFLT03_ALERT_4_G Please check that the estimate of the number of Friedel pairs is correct. If it is not, please give the correct count in the _publ_section_exptl_refinement section of the submitted CIF. From the CIF: _diffrn_reflns_theta_max 26.47 From the CIF: _reflns_number_total 1883 Count of symmetry unique reflns 1896 Completeness (_total/calc) 99.31% TEST3: Check Friedels for noncentro structure Estimate of Friedel pairs measured 0 Fraction of Friedel pairs measured 0.000 Are heavy atom types Z>Si present no
0 ALERT level A = In general: serious problem 1 ALERT level B = Potentially serious problem 7 ALERT level C = Check and explain 1 ALERT level G = General alerts; check 1 ALERT type 1 CIF construction/syntax error, inconsistent or missing data 3 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

Comment top

Carbazole derivatives possess valuable therapeutic properties. In some cases they are able to potentiate the analgesic effect of for example morphine, without substantially influencing the blood pressure and the vegetative nervous system (Chemische Fabrik Promonla GmbH, 1959). N-alkylation is an important process for the construction of carbazole derivatives (Duan et al., 2004). The structure of the title compound, C21H19N, 9-(4-ethylbenzyl)-9H-carbazole, (I), is reported here; it was synthesized by N-alkylation of carbazole with 1-(chloromethyl)-4-ethylbenzene.

The molecular structure of (I) is illustrated in Fig. 1. The carbazole ring is essentially planar, with a mean deviation of 0.003 Å. The dihedral angle between the carbazole plane and that of the major component of the disordered ethyl benzene ring is 72.3 (5)°. Bond lengths and angles are in agreement with reported literature values (Allen et al., 1987). In the crystal structure, there are weak ππ stacking interactions between the ethylbenzene rings at (x − 1/2, −y + 1/2, −z) and (x + 1/2, −y + 1/2, −z); the distance between ring centroids is 5.271 (8). Additional strong C—H···π interactions are observed, the distance between H10a and the centroid of the C1/C2/C3/C4/C5/C6 plane at (1 − x, −1/2 + y, 1/2 − z) being 2.98 Å and that between H13b and the centroid of the C7/C8/C9/C10/C11/C12 plane at (1 + x, y, z) plane being 2.84 Å.

Experimental top

A solution of potassium hydroxide (7.0 g) in DMF (50 ml) was stirred at room temperature for 20 min. Carbazol (3.3 g, 20 mmol) was added and stirred for further 40 min. A solution of 1-(chloromethyl)-4-ethylbenzene (8.5 g, 30 mmol) in DMF (50 ml) was added dropwise with stirring. The resulting mixture was stirred at room temperature for 12 h and poured into 500 ml water to give a white solid product. This was filtered, washed with water and recrystallized from EtOH to give (I). Yield: 4.90 g (85.9%); m.p.: 392.5–393.8 K; 20 mg of (I) was dissolved in 6 ml chloroform, and the solution was kept at room temperature for 10 d. Natural evaporation gave colorless single crystals of (I), suitable for X-ray analysis.

Refinement top

H atoms were included in calculated positions and treated as riding atoms [C—H distances are 0.93 Å for CH and 0.97 Å for CH2 groups, with Uiso(H) = 1.2 Ueq(C), and C—H =0.96 Å for methyl groups, with Uiso(H) = 1.5 Ueq(C). As the absolute structure could not be determined reliably from the diffraction data, Freidel pairs were merged. The ethylbenzene ring was found to be disordered and refined as a regular hexagon with the C—C distances of 1.39 Å. Site occupancies of the two disorder components, which included the atoms of the benzene ring and its ethyl substituent, refined to 0.521 (12) and 0.479 (12) respectively.

Computing details top

Data collection: SMART (Bruker, 1997); cell refinement: SAINT (Bruker, 1997); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: SHELXTL (Bruker, 1997); software used to prepare material for publication: SHELXTL.

Figures top
[Figure 1] Fig. 1. A view of the molecular of (I). Displacement ellipsoids are drawn at the 30% probability level and H atoms are shown as small spheres of arbitrary radii. Only the major component of the disordered ethylbenzene group is shown.
[Figure 2] Fig. 2. A partial packing diagram for (I). Only the major component of the disordered ethylbenzene group is shown.
9-(4-Ethylbenzyl)-9H-carbazole top
Crystal data top
C21H19NDx = 1.205 Mg m3
Mr = 285.37Melting point = 392.5–393.8 K
Orthorhombic, P212121Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2ac 2abCell parameters from 1424 reflections
a = 5.6074 (14) Åθ = 2.5–20.7°
b = 13.943 (3) ŵ = 0.07 mm1
c = 20.124 (5) ÅT = 294 K
V = 1573.4 (7) Å3Block, colorless
Z = 40.22 × 0.16 × 0.14 mm
F(000) = 608
Data collection top
Bruker SMART CCD area-detector
diffractometer
1883 independent reflections
Radiation source: fine-focus sealed tube1028 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.067
ϕ and ω scansθmax = 26.5°, θmin = 1.8°
Absorption correction: multi-scan
(SADABS; Bruker, 1997)
h = 66
Tmin = 0.977, Tmax = 0.990k = 1710
8829 measured reflectionsl = 2524
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)] = 0.045H-atom parameters constrained
wR(F2) = 0.129 w = 1/[σ2(Fo2) + (0.0672P)2]
where P = (Fo2 + 2Fc2)/3
S = 1.00(Δ/σ)max = 0.002
1883 reflectionsΔρmax = 0.22 e Å3
249 parametersΔρmin = 0.12 e Å3
60 restraintsExtinction correction: SHELXL97, Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
Primary atom site location: structure-invariant direct methodsExtinction coefficient: 0.020 (4)
Crystal data top
C21H19NV = 1573.4 (7) Å3
Mr = 285.37Z = 4
Orthorhombic, P212121Mo Kα radiation
a = 5.6074 (14) ŵ = 0.07 mm1
b = 13.943 (3) ÅT = 294 K
c = 20.124 (5) Å0.22 × 0.16 × 0.14 mm
Data collection top
Bruker SMART CCD area-detector
diffractometer
1883 independent reflections
Absorption correction: multi-scan
(SADABS; Bruker, 1997)
1028 reflections with I > 2σ(I)
Tmin = 0.977, Tmax = 0.990Rint = 0.067
8829 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.04560 restraints
wR(F2) = 0.129H-atom parameters constrained
S = 1.00Δρmax = 0.22 e Å3
1883 reflectionsΔρmin = 0.12 e Å3
249 parameters
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*/UeqOcc. (<1)
N10.0961 (5)0.6253 (2)0.25449 (14)0.0600 (8)
C10.1157 (6)0.6745 (3)0.19486 (17)0.0539 (9)
C20.0311 (7)0.7448 (3)0.1685 (2)0.0684 (11)
H2A0.16260.76770.19180.082*
C30.0256 (8)0.7793 (3)0.1066 (2)0.0781 (12)
H3A0.07000.82650.08780.094*
C40.2202 (9)0.7461 (3)0.07156 (19)0.0828 (12)
H4A0.25380.77140.02990.099*
C50.3653 (8)0.6758 (3)0.09757 (18)0.0710 (11)
H5A0.49600.65360.07360.085*
C60.3142 (6)0.6384 (3)0.16013 (17)0.0554 (9)
C70.4180 (6)0.5647 (2)0.20019 (18)0.0563 (9)
C80.6108 (7)0.5028 (3)0.1927 (2)0.0710 (11)
H8A0.70650.50660.15510.085*
C90.6591 (8)0.4363 (3)0.2407 (2)0.0807 (12)
H9A0.78770.39490.23540.097*
C100.5195 (9)0.4300 (3)0.2970 (2)0.0816 (13)
H10A0.55540.38420.32900.098*
C110.3259 (8)0.4909 (3)0.3066 (2)0.0729 (11)
H11A0.23240.48670.34460.087*
C120.2770 (6)0.5576 (3)0.25812 (19)0.0560 (9)
C130.0853 (7)0.6440 (3)0.30498 (18)0.0678 (10)
H13A0.10360.58690.33200.081*
H13B0.23630.65550.28290.081*
C140.032 (2)0.7281 (9)0.3503 (8)0.058 (8)0.521 (12)
C150.2072 (18)0.7976 (9)0.3591 (7)0.073 (5)0.521 (12)
H15A0.34840.79440.33490.087*0.521 (12)
C160.1710 (19)0.8719 (8)0.4040 (8)0.075 (5)0.521 (12)
H16A0.28790.91850.40990.090*0.521 (12)
C170.040 (2)0.8767 (9)0.4401 (7)0.070 (4)0.521 (12)
C180.2148 (19)0.8072 (10)0.4313 (7)0.062 (4)0.521 (12)
H18A0.35600.81040.45540.074*0.521 (12)
C190.1786 (19)0.7328 (8)0.3864 (7)0.059 (4)0.521 (12)
H19A0.29550.68630.38050.071*0.521 (12)
C200.081 (2)0.9641 (9)0.4832 (6)0.119 (5)0.521 (12)
H20A0.08091.01950.45400.143*0.521 (12)
H20B0.05660.97040.51200.143*0.521 (12)
C210.287 (2)0.9713 (9)0.5240 (6)0.160 (6)0.521 (12)
H21A0.26441.02150.55600.240*0.521 (12)
H21B0.42320.98570.49690.240*0.521 (12)
H21C0.31220.91160.54660.240*0.521 (12)
C14'0.019 (3)0.7228 (8)0.3537 (8)0.054 (8)0.479 (12)
C15'0.150 (2)0.8074 (9)0.3562 (7)0.058 (4)0.479 (12)
H15B0.27890.81630.32770.070*0.479 (12)
C16'0.089 (2)0.8786 (8)0.4015 (7)0.065 (4)0.479 (12)
H16B0.17680.93520.40320.078*0.479 (12)
C17'0.103 (3)0.8652 (9)0.4441 (8)0.071 (5)0.479 (12)
C18'0.234 (3)0.7807 (10)0.4416 (8)0.085 (6)0.479 (12)
H18B0.36240.77170.47010.102*0.479 (12)
C19'0.173 (3)0.7095 (8)0.3963 (8)0.072 (5)0.479 (12)
H19B0.26030.65290.39460.087*0.479 (12)
C20'0.152 (3)0.9315 (9)0.5030 (7)0.114 (5)0.479 (12)
H20C0.13380.89470.54360.137*0.479 (12)
H20D0.31670.95230.50060.137*0.479 (12)
C21'0.001 (3)1.0165 (9)0.5077 (8)0.184 (8)0.479 (12)
H21D0.06031.05810.54190.276*0.479 (12)
H21E0.15950.99750.51830.276*0.479 (12)
H21F0.00151.04990.46600.276*0.479 (12)
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
N10.0544 (18)0.0651 (19)0.0605 (18)0.0075 (18)0.0052 (17)0.0063 (17)
C10.049 (2)0.055 (2)0.057 (2)0.0078 (19)0.0073 (19)0.010 (2)
C20.061 (2)0.071 (2)0.073 (2)0.006 (2)0.007 (2)0.009 (2)
C30.084 (3)0.075 (3)0.075 (3)0.009 (3)0.014 (2)0.000 (2)
C40.097 (3)0.089 (3)0.062 (2)0.003 (3)0.011 (3)0.002 (2)
C50.074 (3)0.075 (3)0.064 (2)0.003 (3)0.002 (2)0.012 (2)
C60.055 (2)0.055 (2)0.056 (2)0.0040 (19)0.0053 (19)0.0119 (18)
C70.051 (2)0.052 (2)0.066 (2)0.002 (2)0.005 (2)0.011 (2)
C80.067 (2)0.066 (2)0.080 (3)0.005 (2)0.008 (2)0.017 (2)
C90.082 (3)0.061 (3)0.099 (3)0.013 (2)0.012 (3)0.017 (3)
C100.092 (3)0.057 (3)0.097 (3)0.002 (3)0.027 (3)0.005 (3)
C110.082 (3)0.060 (2)0.076 (2)0.012 (3)0.001 (2)0.008 (2)
C120.050 (2)0.048 (2)0.071 (2)0.0063 (19)0.004 (2)0.006 (2)
C130.052 (2)0.081 (3)0.071 (2)0.014 (2)0.009 (2)0.009 (2)
C140.035 (11)0.092 (16)0.048 (11)0.026 (9)0.012 (8)0.016 (10)
C150.043 (6)0.091 (10)0.085 (9)0.000 (6)0.010 (6)0.008 (7)
C160.043 (8)0.092 (9)0.090 (8)0.008 (6)0.013 (6)0.006 (7)
C170.058 (9)0.069 (8)0.083 (11)0.009 (6)0.007 (6)0.007 (8)
C180.049 (6)0.064 (9)0.072 (7)0.000 (6)0.015 (6)0.011 (7)
C190.048 (7)0.043 (6)0.086 (8)0.009 (5)0.014 (7)0.014 (6)
C200.129 (9)0.119 (9)0.110 (8)0.036 (8)0.028 (7)0.026 (7)
C210.172 (10)0.126 (9)0.181 (9)0.009 (8)0.036 (8)0.061 (7)
C14'0.068 (16)0.040 (10)0.055 (13)0.015 (10)0.020 (11)0.007 (9)
C15'0.036 (6)0.079 (10)0.059 (8)0.000 (6)0.014 (5)0.001 (8)
C16'0.027 (8)0.076 (8)0.092 (9)0.011 (6)0.004 (7)0.015 (7)
C17'0.059 (8)0.090 (13)0.065 (9)0.008 (8)0.017 (7)0.016 (8)
C18'0.115 (11)0.056 (8)0.084 (10)0.000 (7)0.032 (8)0.011 (8)
C19'0.077 (10)0.070 (9)0.069 (8)0.012 (7)0.004 (7)0.010 (8)
C20'0.106 (8)0.109 (8)0.129 (9)0.020 (7)0.059 (7)0.022 (7)
C21'0.199 (12)0.170 (11)0.184 (11)0.003 (9)0.010 (9)0.055 (9)
Geometric parameters (Å, º) top
N1—C11.386 (4)C15—H15A0.9300
N1—C121.388 (4)C16—C171.3900
N1—C131.461 (4)C16—H16A0.9300
C1—C21.386 (5)C17—C181.3900
C1—C61.407 (5)C17—C201.514 (8)
C2—C31.372 (5)C18—C191.3900
C2—H2A0.9300C18—H18A0.9300
C3—C41.380 (5)C19—H19A0.9300
C3—H3A0.9300C20—C211.420 (9)
C4—C51.377 (5)C20—H20A0.9700
C4—H4A0.9300C20—H20B0.9700
C5—C61.392 (5)C21—H21A0.9600
C5—H5A0.9300C21—H21B0.9600
C6—C71.430 (5)C21—H21C0.9600
C7—C81.392 (5)C14'—C15'1.3900
C7—C121.412 (5)C14'—C19'1.3900
C8—C91.365 (5)C15'—C16'1.3900
C8—H8A0.9300C15'—H15B0.9300
C9—C101.380 (6)C16'—C17'1.3900
C9—H9A0.9300C16'—H16B0.9300
C10—C111.392 (6)C17'—C18'1.3900
C10—H10A0.9300C17'—C20'1.527 (8)
C11—C121.375 (5)C18'—C19'1.3900
C11—H11A0.9300C18'—H18B0.9300
C13—C141.514 (6)C19'—H19B0.9300
C13—C14'1.518 (6)C20'—C21'1.460 (10)
C13—H13A0.9700C20'—H20C0.9700
C13—H13B0.9700C20'—H20D0.9700
C14—C151.3900C21'—H21D0.9600
C14—C191.3900C21'—H21E0.9600
C15—C161.3900C21'—H21F0.9600
C1—N1—C12108.9 (3)C17—C16—C15120.0
C1—N1—C13124.7 (3)C17—C16—H16A120.0
C12—N1—C13126.4 (3)C15—C16—H16A120.0
N1—C1—C2129.4 (3)C16—C17—C18120.0
N1—C1—C6108.4 (3)C16—C17—C20117.9 (7)
C2—C1—C6122.2 (3)C18—C17—C20121.9 (6)
C3—C2—C1117.3 (4)C19—C18—C17120.0
C3—C2—H2A121.4C19—C18—H18A120.0
C1—C2—H2A121.4C17—C18—H18A120.0
C2—C3—C4122.0 (4)C18—C19—C14120.0
C2—C3—H3A119.0C18—C19—H19A120.0
C4—C3—H3A119.0C14—C19—H19A120.0
C5—C4—C3120.8 (4)C21—C20—C17120.8 (9)
C5—C4—H4A119.6C21—C20—H20A107.1
C3—C4—H4A119.6C17—C20—H20A107.1
C4—C5—C6119.2 (4)C21—C20—H20B107.1
C4—C5—H5A120.4C17—C20—H20B107.1
C6—C5—H5A120.4H20A—C20—H20B106.8
C5—C6—C1118.6 (4)C20—C21—H21A109.5
C5—C6—C7134.0 (4)C20—C21—H21B109.5
C1—C6—C7107.4 (3)H21A—C21—H21B109.5
C8—C7—C12118.7 (3)C20—C21—H21C109.5
C8—C7—C6134.5 (4)H21A—C21—H21C109.5
C12—C7—C6106.7 (3)H21B—C21—H21C109.5
C9—C8—C7119.9 (4)C15'—C14'—C19'120.0
C9—C8—H8A120.0C15'—C14'—C13120.6 (6)
C7—C8—H8A120.0C19'—C14'—C13119.4 (6)
C8—C9—C10120.8 (4)C16'—C15'—C14'120.0
C8—C9—H9A119.6C16'—C15'—H15B120.0
C10—C9—H9A119.6C14'—C15'—H15B120.0
C9—C10—C11121.2 (4)C15'—C16'—C17'120.0
C9—C10—H10A119.4C15'—C16'—H16B120.0
C11—C10—H10A119.4C17'—C16'—H16B120.0
C12—C11—C10118.0 (4)C18'—C17'—C16'120.0
C12—C11—H11A121.0C18'—C17'—C20'116.6 (7)
C10—C11—H11A121.0C16'—C17'—C20'122.5 (7)
C11—C12—N1130.0 (4)C19'—C18'—C17'120.0
C11—C12—C7121.4 (3)C19'—C18'—H18B120.0
N1—C12—C7108.5 (3)C17'—C18'—H18B120.0
N1—C13—C14114.9 (7)C18'—C19'—C14'120.0
N1—C13—C14'114.1 (8)C18'—C19'—H19B120.0
C14—C13—C14'4.7 (9)C14'—C19'—H19B120.0
N1—C13—H13A108.6C21'—C20'—C17'115.9 (9)
C14—C13—H13A108.6C21'—C20'—H20C108.3
C14'—C13—H13A104.9C17'—C20'—H20C108.3
N1—C13—H13B108.6C21'—C20'—H20D108.3
C14—C13—H13B108.6C17'—C20'—H20D108.3
C14'—C13—H13B112.8H20C—C20'—H20D107.4
H13A—C13—H13B107.5C20'—C21'—H21D109.5
C15—C14—C19120.0C20'—C21'—H21E109.5
C15—C14—C13118.6 (6)H21D—C21'—H21E109.5
C19—C14—C13121.2 (6)C20'—C21'—H21F109.5
C16—C15—C14120.0H21D—C21'—H21F109.5
C16—C15—H15A120.0H21E—C21'—H21F109.5
C14—C15—H15A120.0
C12—N1—C1—C2176.6 (3)C12—N1—C13—C1498.1 (7)
C13—N1—C1—C24.1 (5)C1—N1—C13—C14'86.1 (7)
C12—N1—C1—C60.8 (3)C12—N1—C13—C14'93.0 (7)
C13—N1—C1—C6178.5 (3)N1—C13—C14—C15129.1 (8)
N1—C1—C2—C3177.7 (3)C14'—C13—C14—C15149 (18)
C6—C1—C2—C30.5 (5)N1—C13—C14—C1955.6 (12)
C1—C2—C3—C40.0 (6)C14'—C13—C14—C1926 (16)
C2—C3—C4—C50.4 (6)C19—C14—C15—C160.0
C3—C4—C5—C60.2 (6)C13—C14—C15—C16175.3 (15)
C4—C5—C6—C10.4 (5)C14—C15—C16—C170.0
C4—C5—C6—C7177.3 (4)C15—C16—C17—C180.0
N1—C1—C6—C5178.4 (3)C15—C16—C17—C20174.1 (16)
C2—C1—C6—C50.8 (5)C16—C17—C18—C190.0
N1—C1—C6—C70.1 (3)C20—C17—C18—C19173.8 (16)
C2—C1—C6—C7177.5 (3)C17—C18—C19—C140.0
C5—C6—C7—C80.9 (7)C15—C14—C19—C180.0
C1—C6—C7—C8178.8 (4)C13—C14—C19—C18175.2 (15)
C5—C6—C7—C12177.4 (4)C16—C17—C20—C21176.7 (13)
C1—C6—C7—C120.5 (4)C18—C17—C20—C219 (2)
C12—C7—C8—C90.5 (5)N1—C13—C14'—C15'115.4 (9)
C6—C7—C8—C9177.6 (4)C14—C13—C14'—C15'15 (16)
C7—C8—C9—C100.3 (6)N1—C13—C14'—C19'65.2 (12)
C8—C9—C10—C110.1 (6)C14—C13—C14'—C19'165 (18)
C9—C10—C11—C120.3 (5)C19'—C14'—C15'—C16'0.0
C10—C11—C12—N1179.1 (3)C13—C14'—C15'—C16'179.5 (16)
C10—C11—C12—C70.1 (5)C14'—C15'—C16'—C17'0.0
C1—N1—C12—C11178.1 (4)C15'—C16'—C17'—C18'0.0
C13—N1—C12—C112.6 (5)C15'—C16'—C17'—C20'168.6 (18)
C1—N1—C12—C71.1 (3)C16'—C17'—C18'—C19'0.0
C13—N1—C12—C7178.1 (3)C20'—C17'—C18'—C19'169.2 (17)
C8—C7—C12—C110.3 (5)C17'—C18'—C19'—C14'0.0
C6—C7—C12—C11178.3 (3)C15'—C14'—C19'—C18'0.0
C8—C7—C12—N1179.6 (3)C13—C14'—C19'—C18'179.5 (16)
C6—C7—C12—N11.0 (4)C18'—C17'—C20'—C21'175.6 (12)
C1—N1—C13—C1481.0 (7)C16'—C17'—C20'—C21'7 (2)

Experimental details

Crystal data
Chemical formulaC21H19N
Mr285.37
Crystal system, space groupOrthorhombic, P212121
Temperature (K)294
a, b, c (Å)5.6074 (14), 13.943 (3), 20.124 (5)
V3)1573.4 (7)
Z4
Radiation typeMo Kα
µ (mm1)0.07
Crystal size (mm)0.22 × 0.16 × 0.14
Data collection
DiffractometerBruker SMART CCD area-detector
diffractometer
Absorption correctionMulti-scan
(SADABS; Bruker, 1997)
Tmin, Tmax0.977, 0.990
No. of measured, independent and
observed [I > 2σ(I)] reflections
8829, 1883, 1028
Rint0.067
(sin θ/λ)max1)0.627
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.045, 0.129, 1.00
No. of reflections1883
No. of parameters249
No. of restraints60
H-atom treatmentH-atom parameters constrained
Δρmax, Δρmin (e Å3)0.22, 0.12

Computer programs: SMART (Bruker, 1997), SAINT (Bruker, 1997), SAINT, SHELXS97 (Sheldrick, 1997), SHELXL97 (Sheldrick, 1997), SHELXTL (Bruker, 1997), SHELXTL.

 

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