Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536805040195/sj6166sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S1600536805040195/sj6166Isup2.hkl |
CCDC reference: 296726
Key indicators
- Single-crystal X-ray study
- T = 294 K
- Mean (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
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.
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.
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.
C21H19N | Dx = 1.205 Mg m−3 |
Mr = 285.37 | Melting point = 392.5–393.8 K |
Orthorhombic, P212121 | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: P 2ac 2ab | Cell parameters from 1424 reflections |
a = 5.6074 (14) Å | θ = 2.5–20.7° |
b = 13.943 (3) Å | µ = 0.07 mm−1 |
c = 20.124 (5) Å | T = 294 K |
V = 1573.4 (7) Å3 | Block, colorless |
Z = 4 | 0.22 × 0.16 × 0.14 mm |
F(000) = 608 |
Bruker SMART CCD area-detector diffractometer | 1883 independent reflections |
Radiation source: fine-focus sealed tube | 1028 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.067 |
ϕ and ω scans | θmax = 26.5°, θmin = 1.8° |
Absorption correction: multi-scan (SADABS; Bruker, 1997) | h = −6→6 |
Tmin = 0.977, Tmax = 0.990 | k = −17→10 |
8829 measured reflections | l = −25→24 |
Refinement on F2 | Secondary atom site location: difference Fourier map |
Least-squares matrix: full | Hydrogen site location: inferred from neighbouring sites |
R[F2 > 2σ(F2)] = 0.045 | H-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 reflections | Δρmax = 0.22 e Å−3 |
249 parameters | Δρmin = −0.12 e Å−3 |
60 restraints | Extinction correction: SHELXL97, Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4 |
Primary atom site location: structure-invariant direct methods | Extinction coefficient: 0.020 (4) |
C21H19N | V = 1573.4 (7) Å3 |
Mr = 285.37 | Z = 4 |
Orthorhombic, P212121 | Mo Kα radiation |
a = 5.6074 (14) Å | µ = 0.07 mm−1 |
b = 13.943 (3) Å | T = 294 K |
c = 20.124 (5) Å | 0.22 × 0.16 × 0.14 mm |
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 = 0.990 | Rint = 0.067 |
8829 measured reflections |
R[F2 > 2σ(F2)] = 0.045 | 60 restraints |
wR(F2) = 0.129 | H-atom parameters constrained |
S = 1.00 | Δρmax = 0.22 e Å−3 |
1883 reflections | Δρmin = −0.12 e Å−3 |
249 parameters |
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. |
x | y | z | Uiso*/Ueq | Occ. (<1) | |
N1 | 0.0961 (5) | 0.6253 (2) | 0.25449 (14) | 0.0600 (8) | |
C1 | 0.1157 (6) | 0.6745 (3) | 0.19486 (17) | 0.0539 (9) | |
C2 | −0.0311 (7) | 0.7448 (3) | 0.1685 (2) | 0.0684 (11) | |
H2A | −0.1626 | 0.7677 | 0.1918 | 0.082* | |
C3 | 0.0256 (8) | 0.7793 (3) | 0.1066 (2) | 0.0781 (12) | |
H3A | −0.0700 | 0.8265 | 0.0878 | 0.094* | |
C4 | 0.2202 (9) | 0.7461 (3) | 0.07156 (19) | 0.0828 (12) | |
H4A | 0.2538 | 0.7714 | 0.0299 | 0.099* | |
C5 | 0.3653 (8) | 0.6758 (3) | 0.09757 (18) | 0.0710 (11) | |
H5A | 0.4960 | 0.6536 | 0.0736 | 0.085* | |
C6 | 0.3142 (6) | 0.6384 (3) | 0.16013 (17) | 0.0554 (9) | |
C7 | 0.4180 (6) | 0.5647 (2) | 0.20019 (18) | 0.0563 (9) | |
C8 | 0.6108 (7) | 0.5028 (3) | 0.1927 (2) | 0.0710 (11) | |
H8A | 0.7065 | 0.5066 | 0.1551 | 0.085* | |
C9 | 0.6591 (8) | 0.4363 (3) | 0.2407 (2) | 0.0807 (12) | |
H9A | 0.7877 | 0.3949 | 0.2354 | 0.097* | |
C10 | 0.5195 (9) | 0.4300 (3) | 0.2970 (2) | 0.0816 (13) | |
H10A | 0.5554 | 0.3842 | 0.3290 | 0.098* | |
C11 | 0.3259 (8) | 0.4909 (3) | 0.3066 (2) | 0.0729 (11) | |
H11A | 0.2324 | 0.4867 | 0.3446 | 0.087* | |
C12 | 0.2770 (6) | 0.5576 (3) | 0.25812 (19) | 0.0560 (9) | |
C13 | −0.0853 (7) | 0.6440 (3) | 0.30498 (18) | 0.0678 (10) | |
H13A | −0.1036 | 0.5869 | 0.3320 | 0.081* | |
H13B | −0.2363 | 0.6555 | 0.2829 | 0.081* | |
C14 | −0.032 (2) | 0.7281 (9) | 0.3503 (8) | 0.058 (8) | 0.521 (12) |
C15 | −0.2072 (18) | 0.7976 (9) | 0.3591 (7) | 0.073 (5) | 0.521 (12) |
H15A | −0.3484 | 0.7944 | 0.3349 | 0.087* | 0.521 (12) |
C16 | −0.1710 (19) | 0.8719 (8) | 0.4040 (8) | 0.075 (5) | 0.521 (12) |
H16A | −0.2879 | 0.9185 | 0.4099 | 0.090* | 0.521 (12) |
C17 | 0.040 (2) | 0.8767 (9) | 0.4401 (7) | 0.070 (4) | 0.521 (12) |
C18 | 0.2148 (19) | 0.8072 (10) | 0.4313 (7) | 0.062 (4) | 0.521 (12) |
H18A | 0.3560 | 0.8104 | 0.4554 | 0.074* | 0.521 (12) |
C19 | 0.1786 (19) | 0.7328 (8) | 0.3864 (7) | 0.059 (4) | 0.521 (12) |
H19A | 0.2955 | 0.6863 | 0.3805 | 0.071* | 0.521 (12) |
C20 | 0.081 (2) | 0.9641 (9) | 0.4832 (6) | 0.119 (5) | 0.521 (12) |
H20A | 0.0809 | 1.0195 | 0.4540 | 0.143* | 0.521 (12) |
H20B | −0.0566 | 0.9704 | 0.5120 | 0.143* | 0.521 (12) |
C21 | 0.287 (2) | 0.9713 (9) | 0.5240 (6) | 0.160 (6) | 0.521 (12) |
H21A | 0.2644 | 1.0215 | 0.5560 | 0.240* | 0.521 (12) |
H21B | 0.4232 | 0.9857 | 0.4969 | 0.240* | 0.521 (12) |
H21C | 0.3122 | 0.9116 | 0.5466 | 0.240* | 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) |
H15B | −0.2789 | 0.8163 | 0.3277 | 0.070* | 0.479 (12) |
C16' | −0.089 (2) | 0.8786 (8) | 0.4015 (7) | 0.065 (4) | 0.479 (12) |
H16B | −0.1768 | 0.9352 | 0.4032 | 0.078* | 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) |
H18B | 0.3624 | 0.7717 | 0.4701 | 0.102* | 0.479 (12) |
C19' | 0.173 (3) | 0.7095 (8) | 0.3963 (8) | 0.072 (5) | 0.479 (12) |
H19B | 0.2603 | 0.6529 | 0.3946 | 0.087* | 0.479 (12) |
C20' | 0.152 (3) | 0.9315 (9) | 0.5030 (7) | 0.114 (5) | 0.479 (12) |
H20C | 0.1338 | 0.8947 | 0.5436 | 0.137* | 0.479 (12) |
H20D | 0.3167 | 0.9523 | 0.5006 | 0.137* | 0.479 (12) |
C21' | 0.001 (3) | 1.0165 (9) | 0.5077 (8) | 0.184 (8) | 0.479 (12) |
H21D | 0.0603 | 1.0581 | 0.5419 | 0.276* | 0.479 (12) |
H21E | −0.1595 | 0.9975 | 0.5183 | 0.276* | 0.479 (12) |
H21F | 0.0015 | 1.0499 | 0.4660 | 0.276* | 0.479 (12) |
U11 | U22 | U33 | U12 | U13 | U23 | |
N1 | 0.0544 (18) | 0.0651 (19) | 0.0605 (18) | −0.0075 (18) | 0.0052 (17) | −0.0063 (17) |
C1 | 0.049 (2) | 0.055 (2) | 0.057 (2) | −0.0078 (19) | −0.0073 (19) | −0.010 (2) |
C2 | 0.061 (2) | 0.071 (2) | 0.073 (2) | 0.006 (2) | −0.007 (2) | −0.009 (2) |
C3 | 0.084 (3) | 0.075 (3) | 0.075 (3) | 0.009 (3) | −0.014 (2) | 0.000 (2) |
C4 | 0.097 (3) | 0.089 (3) | 0.062 (2) | 0.003 (3) | −0.011 (3) | 0.002 (2) |
C5 | 0.074 (3) | 0.075 (3) | 0.064 (2) | 0.003 (3) | 0.002 (2) | −0.012 (2) |
C6 | 0.055 (2) | 0.055 (2) | 0.056 (2) | −0.0040 (19) | −0.0053 (19) | −0.0119 (18) |
C7 | 0.051 (2) | 0.052 (2) | 0.066 (2) | −0.002 (2) | −0.005 (2) | −0.011 (2) |
C8 | 0.067 (2) | 0.066 (2) | 0.080 (3) | 0.005 (2) | −0.008 (2) | −0.017 (2) |
C9 | 0.082 (3) | 0.061 (3) | 0.099 (3) | 0.013 (2) | −0.012 (3) | −0.017 (3) |
C10 | 0.092 (3) | 0.057 (3) | 0.097 (3) | −0.002 (3) | −0.027 (3) | 0.005 (3) |
C11 | 0.082 (3) | 0.060 (2) | 0.076 (2) | −0.012 (3) | −0.001 (2) | 0.008 (2) |
C12 | 0.050 (2) | 0.048 (2) | 0.071 (2) | −0.0063 (19) | −0.004 (2) | −0.006 (2) |
C13 | 0.052 (2) | 0.081 (3) | 0.071 (2) | −0.014 (2) | 0.009 (2) | −0.009 (2) |
C14 | 0.035 (11) | 0.092 (16) | 0.048 (11) | −0.026 (9) | −0.012 (8) | 0.016 (10) |
C15 | 0.043 (6) | 0.091 (10) | 0.085 (9) | 0.000 (6) | 0.010 (6) | −0.008 (7) |
C16 | 0.043 (8) | 0.092 (9) | 0.090 (8) | 0.008 (6) | 0.013 (6) | −0.006 (7) |
C17 | 0.058 (9) | 0.069 (8) | 0.083 (11) | 0.009 (6) | 0.007 (6) | −0.007 (8) |
C18 | 0.049 (6) | 0.064 (9) | 0.072 (7) | 0.000 (6) | −0.015 (6) | 0.011 (7) |
C19 | 0.048 (7) | 0.043 (6) | 0.086 (8) | 0.009 (5) | −0.014 (7) | 0.014 (6) |
C20 | 0.129 (9) | 0.119 (9) | 0.110 (8) | 0.036 (8) | −0.028 (7) | −0.026 (7) |
C21 | 0.172 (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) |
N1—C1 | 1.386 (4) | C15—H15A | 0.9300 |
N1—C12 | 1.388 (4) | C16—C17 | 1.3900 |
N1—C13 | 1.461 (4) | C16—H16A | 0.9300 |
C1—C2 | 1.386 (5) | C17—C18 | 1.3900 |
C1—C6 | 1.407 (5) | C17—C20 | 1.514 (8) |
C2—C3 | 1.372 (5) | C18—C19 | 1.3900 |
C2—H2A | 0.9300 | C18—H18A | 0.9300 |
C3—C4 | 1.380 (5) | C19—H19A | 0.9300 |
C3—H3A | 0.9300 | C20—C21 | 1.420 (9) |
C4—C5 | 1.377 (5) | C20—H20A | 0.9700 |
C4—H4A | 0.9300 | C20—H20B | 0.9700 |
C5—C6 | 1.392 (5) | C21—H21A | 0.9600 |
C5—H5A | 0.9300 | C21—H21B | 0.9600 |
C6—C7 | 1.430 (5) | C21—H21C | 0.9600 |
C7—C8 | 1.392 (5) | C14'—C15' | 1.3900 |
C7—C12 | 1.412 (5) | C14'—C19' | 1.3900 |
C8—C9 | 1.365 (5) | C15'—C16' | 1.3900 |
C8—H8A | 0.9300 | C15'—H15B | 0.9300 |
C9—C10 | 1.380 (6) | C16'—C17' | 1.3900 |
C9—H9A | 0.9300 | C16'—H16B | 0.9300 |
C10—C11 | 1.392 (6) | C17'—C18' | 1.3900 |
C10—H10A | 0.9300 | C17'—C20' | 1.527 (8) |
C11—C12 | 1.375 (5) | C18'—C19' | 1.3900 |
C11—H11A | 0.9300 | C18'—H18B | 0.9300 |
C13—C14 | 1.514 (6) | C19'—H19B | 0.9300 |
C13—C14' | 1.518 (6) | C20'—C21' | 1.460 (10) |
C13—H13A | 0.9700 | C20'—H20C | 0.9700 |
C13—H13B | 0.9700 | C20'—H20D | 0.9700 |
C14—C15 | 1.3900 | C21'—H21D | 0.9600 |
C14—C19 | 1.3900 | C21'—H21E | 0.9600 |
C15—C16 | 1.3900 | C21'—H21F | 0.9600 |
C1—N1—C12 | 108.9 (3) | C17—C16—C15 | 120.0 |
C1—N1—C13 | 124.7 (3) | C17—C16—H16A | 120.0 |
C12—N1—C13 | 126.4 (3) | C15—C16—H16A | 120.0 |
N1—C1—C2 | 129.4 (3) | C16—C17—C18 | 120.0 |
N1—C1—C6 | 108.4 (3) | C16—C17—C20 | 117.9 (7) |
C2—C1—C6 | 122.2 (3) | C18—C17—C20 | 121.9 (6) |
C3—C2—C1 | 117.3 (4) | C19—C18—C17 | 120.0 |
C3—C2—H2A | 121.4 | C19—C18—H18A | 120.0 |
C1—C2—H2A | 121.4 | C17—C18—H18A | 120.0 |
C2—C3—C4 | 122.0 (4) | C18—C19—C14 | 120.0 |
C2—C3—H3A | 119.0 | C18—C19—H19A | 120.0 |
C4—C3—H3A | 119.0 | C14—C19—H19A | 120.0 |
C5—C4—C3 | 120.8 (4) | C21—C20—C17 | 120.8 (9) |
C5—C4—H4A | 119.6 | C21—C20—H20A | 107.1 |
C3—C4—H4A | 119.6 | C17—C20—H20A | 107.1 |
C4—C5—C6 | 119.2 (4) | C21—C20—H20B | 107.1 |
C4—C5—H5A | 120.4 | C17—C20—H20B | 107.1 |
C6—C5—H5A | 120.4 | H20A—C20—H20B | 106.8 |
C5—C6—C1 | 118.6 (4) | C20—C21—H21A | 109.5 |
C5—C6—C7 | 134.0 (4) | C20—C21—H21B | 109.5 |
C1—C6—C7 | 107.4 (3) | H21A—C21—H21B | 109.5 |
C8—C7—C12 | 118.7 (3) | C20—C21—H21C | 109.5 |
C8—C7—C6 | 134.5 (4) | H21A—C21—H21C | 109.5 |
C12—C7—C6 | 106.7 (3) | H21B—C21—H21C | 109.5 |
C9—C8—C7 | 119.9 (4) | C15'—C14'—C19' | 120.0 |
C9—C8—H8A | 120.0 | C15'—C14'—C13 | 120.6 (6) |
C7—C8—H8A | 120.0 | C19'—C14'—C13 | 119.4 (6) |
C8—C9—C10 | 120.8 (4) | C16'—C15'—C14' | 120.0 |
C8—C9—H9A | 119.6 | C16'—C15'—H15B | 120.0 |
C10—C9—H9A | 119.6 | C14'—C15'—H15B | 120.0 |
C9—C10—C11 | 121.2 (4) | C15'—C16'—C17' | 120.0 |
C9—C10—H10A | 119.4 | C15'—C16'—H16B | 120.0 |
C11—C10—H10A | 119.4 | C17'—C16'—H16B | 120.0 |
C12—C11—C10 | 118.0 (4) | C18'—C17'—C16' | 120.0 |
C12—C11—H11A | 121.0 | C18'—C17'—C20' | 116.6 (7) |
C10—C11—H11A | 121.0 | C16'—C17'—C20' | 122.5 (7) |
C11—C12—N1 | 130.0 (4) | C19'—C18'—C17' | 120.0 |
C11—C12—C7 | 121.4 (3) | C19'—C18'—H18B | 120.0 |
N1—C12—C7 | 108.5 (3) | C17'—C18'—H18B | 120.0 |
N1—C13—C14 | 114.9 (7) | C18'—C19'—C14' | 120.0 |
N1—C13—C14' | 114.1 (8) | C18'—C19'—H19B | 120.0 |
C14—C13—C14' | 4.7 (9) | C14'—C19'—H19B | 120.0 |
N1—C13—H13A | 108.6 | C21'—C20'—C17' | 115.9 (9) |
C14—C13—H13A | 108.6 | C21'—C20'—H20C | 108.3 |
C14'—C13—H13A | 104.9 | C17'—C20'—H20C | 108.3 |
N1—C13—H13B | 108.6 | C21'—C20'—H20D | 108.3 |
C14—C13—H13B | 108.6 | C17'—C20'—H20D | 108.3 |
C14'—C13—H13B | 112.8 | H20C—C20'—H20D | 107.4 |
H13A—C13—H13B | 107.5 | C20'—C21'—H21D | 109.5 |
C15—C14—C19 | 120.0 | C20'—C21'—H21E | 109.5 |
C15—C14—C13 | 118.6 (6) | H21D—C21'—H21E | 109.5 |
C19—C14—C13 | 121.2 (6) | C20'—C21'—H21F | 109.5 |
C16—C15—C14 | 120.0 | H21D—C21'—H21F | 109.5 |
C16—C15—H15A | 120.0 | H21E—C21'—H21F | 109.5 |
C14—C15—H15A | 120.0 | ||
C12—N1—C1—C2 | 176.6 (3) | C12—N1—C13—C14 | 98.1 (7) |
C13—N1—C1—C2 | −4.1 (5) | C1—N1—C13—C14' | −86.1 (7) |
C12—N1—C1—C6 | −0.8 (3) | C12—N1—C13—C14' | 93.0 (7) |
C13—N1—C1—C6 | 178.5 (3) | N1—C13—C14—C15 | 129.1 (8) |
N1—C1—C2—C3 | −177.7 (3) | C14'—C13—C14—C15 | −149 (18) |
C6—C1—C2—C3 | −0.5 (5) | N1—C13—C14—C19 | −55.6 (12) |
C1—C2—C3—C4 | 0.0 (6) | C14'—C13—C14—C19 | 26 (16) |
C2—C3—C4—C5 | 0.4 (6) | C19—C14—C15—C16 | 0.0 |
C3—C4—C5—C6 | −0.2 (6) | C13—C14—C15—C16 | 175.3 (15) |
C4—C5—C6—C1 | −0.4 (5) | C14—C15—C16—C17 | 0.0 |
C4—C5—C6—C7 | 177.3 (4) | C15—C16—C17—C18 | 0.0 |
N1—C1—C6—C5 | 178.4 (3) | C15—C16—C17—C20 | 174.1 (16) |
C2—C1—C6—C5 | 0.8 (5) | C16—C17—C18—C19 | 0.0 |
N1—C1—C6—C7 | 0.1 (3) | C20—C17—C18—C19 | −173.8 (16) |
C2—C1—C6—C7 | −177.5 (3) | C17—C18—C19—C14 | 0.0 |
C5—C6—C7—C8 | 0.9 (7) | C15—C14—C19—C18 | 0.0 |
C1—C6—C7—C8 | 178.8 (4) | C13—C14—C19—C18 | −175.2 (15) |
C5—C6—C7—C12 | −177.4 (4) | C16—C17—C20—C21 | 176.7 (13) |
C1—C6—C7—C12 | 0.5 (4) | C18—C17—C20—C21 | −9 (2) |
C12—C7—C8—C9 | 0.5 (5) | N1—C13—C14'—C15' | 115.4 (9) |
C6—C7—C8—C9 | −177.6 (4) | C14—C13—C14'—C15' | 15 (16) |
C7—C8—C9—C10 | −0.3 (6) | N1—C13—C14'—C19' | −65.2 (12) |
C8—C9—C10—C11 | −0.1 (6) | C14—C13—C14'—C19' | −165 (18) |
C9—C10—C11—C12 | 0.3 (5) | C19'—C14'—C15'—C16' | 0.0 |
C10—C11—C12—N1 | 179.1 (3) | C13—C14'—C15'—C16' | 179.5 (16) |
C10—C11—C12—C7 | −0.1 (5) | C14'—C15'—C16'—C17' | 0.0 |
C1—N1—C12—C11 | −178.1 (4) | C15'—C16'—C17'—C18' | 0.0 |
C13—N1—C12—C11 | 2.6 (5) | C15'—C16'—C17'—C20' | −168.6 (18) |
C1—N1—C12—C7 | 1.1 (3) | C16'—C17'—C18'—C19' | 0.0 |
C13—N1—C12—C7 | −178.1 (3) | C20'—C17'—C18'—C19' | 169.2 (17) |
C8—C7—C12—C11 | −0.3 (5) | C17'—C18'—C19'—C14' | 0.0 |
C6—C7—C12—C11 | 178.3 (3) | C15'—C14'—C19'—C18' | 0.0 |
C8—C7—C12—N1 | −179.6 (3) | C13—C14'—C19'—C18' | −179.5 (16) |
C6—C7—C12—N1 | −1.0 (4) | C18'—C17'—C20'—C21' | −175.6 (12) |
C1—N1—C13—C14 | −81.0 (7) | C16'—C17'—C20'—C21' | −7 (2) |
Experimental details
Crystal data | |
Chemical formula | C21H19N |
Mr | 285.37 |
Crystal system, space group | Orthorhombic, P212121 |
Temperature (K) | 294 |
a, b, c (Å) | 5.6074 (14), 13.943 (3), 20.124 (5) |
V (Å3) | 1573.4 (7) |
Z | 4 |
Radiation type | Mo Kα |
µ (mm−1) | 0.07 |
Crystal size (mm) | 0.22 × 0.16 × 0.14 |
Data collection | |
Diffractometer | Bruker SMART CCD area-detector diffractometer |
Absorption correction | Multi-scan (SADABS; Bruker, 1997) |
Tmin, Tmax | 0.977, 0.990 |
No. of measured, independent and observed [I > 2σ(I)] reflections | 8829, 1883, 1028 |
Rint | 0.067 |
(sin θ/λ)max (Å−1) | 0.627 |
Refinement | |
R[F2 > 2σ(F2)], wR(F2), S | 0.045, 0.129, 1.00 |
No. of reflections | 1883 |
No. of parameters | 249 |
No. of restraints | 60 |
H-atom treatment | H-atom parameters constrained |
Δρmax, Δρmin (e Å−3) | 0.22, −0.12 |
Computer programs: SMART (Bruker, 1997), SAINT (Bruker, 1997), SAINT, SHELXS97 (Sheldrick, 1997), SHELXL97 (Sheldrick, 1997), SHELXTL (Bruker, 1997), SHELXTL.
Subscribe to Acta Crystallographica Section E: Crystallographic Communications
The full text of this article is available to subscribers to the journal.
- Information on subscribing
- Sample issue
- If you have already subscribed, you may need to register
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 π–π 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.