Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536805040201/ww6463sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S1600536805040201/ww6463Isup2.hkl |
CCDC reference: 296706
Key indicators
- Single-crystal X-ray study
- T = 294 K
- Mean (C-C) = 0.003 Å
- R factor = 0.037
- wR factor = 0.091
- Data-to-parameter ratio = 9.3
checkCIF/PLATON results
No syntax errors found
Alert level C PLAT242_ALERT_2_C Check Low Ueq as Compared to Neighbors for C17
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 26.45 From the CIF: _reflns_number_total 1783 Count of symmetry unique reflns 1785 Completeness (_total/calc) 99.89% 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 0 ALERT level B = Potentially serious problem 1 ALERT level C = Check and explain 1 ALERT level G = General alerts; check 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 0 ALERT type 3 Indicator that the structure quality may be low 1 ALERT type 4 Improvement, methodology, query or suggestion
The title compound was prepared according to the procedure of Duan et al. (2005). A solution of potassium hydroxide (7.0 g) in dimethylformamide (50 ml) was stirred at room temperature for 20 min. Carbazole (3.34 g, 20 mmol) was added and the mixture stirred for a further 40 min. A solution of with 1-chloromethyl-4-methyl-benzene(4.23 g, 30 mmol) in dimethylformamide (50 ml) was added dropwise with stirring. The resulting mixture was then stirred at room temperature for 12 h and poured into water (500 ml), yielding a white precipitate. The solid product was filtered off, washed with cold water and recrystallized from EtOH, giving crystals of (I). Yield: 4.89 g (90.2%); m.p. 390 K. Compound (I) (40 mg) was dissolved in a mixture of chloroform (5 ml) and ethanol (5 ml) and the solution was kept at room temperature for 18 d. Natural evaporation of the solution gave colourless crystals suitable for X-Ray analysis.
All H atoms were included in the riding model approximation with C—H distances = 0.93 (aromatic), 0.96 (methyl) and 0.97 (methene) Å, and with Uiso(H) = 1.2Ueq(C).
Data collection: SMART (Bruker, 1997); cell refinement: SMART; data reduction: SAINT (Bruker, 1997); 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.
Fig. 1. A view of the molecular structure of (I). Displacement ellopsoids are drawn at the 30% probability level. |
C20H17N | Dx = 1.212 Mg m−3 |
Mr = 271.35 | Melting point: 390 K |
Orthorhombic, P212121 | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: P 2ac 2ab | Cell parameters from 2354 reflections |
a = 5.6128 (10) Å | θ = 2.6–24.7° |
b = 13.627 (3) Å | µ = 0.07 mm−1 |
c = 19.442 (4) Å | T = 294 K |
V = 1487.0 (5) Å3 | Rod, colourless |
Z = 4 | 0.24 × 0.20 × 0.10 mm |
F(000) = 576 |
Bruker SMART CCD area-detector diffractometer | 1783 independent reflections |
Radiation source: fine-focus sealed tube | 1305 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.038 |
ϕ and ω scans | θmax = 26.5°, θmin = 1.8° |
Absorption correction: multi-scan (SADABS; Bruker, 1997) | h = −7→6 |
Tmin = 0.978, Tmax = 0.993 | k = −17→13 |
8438 measured reflections | l = −24→23 |
Refinement on F2 | Primary atom site location: structure-invariant direct methods |
Least-squares matrix: full | Secondary atom site location: difference Fourier map |
R[F2 > 2σ(F2)] = 0.037 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.091 | H-atom parameters constrained |
S = 1.05 | w = 1/[σ2(Fo2) + (0.0475P)2 + 0.0342P] where P = (Fo2 + 2Fc2)/3 |
1783 reflections | (Δ/σ)max = 0.002 |
191 parameters | Δρmax = 0.11 e Å−3 |
0 restraints | Δρmin = −0.16 e Å−3 |
C20H17N | V = 1487.0 (5) Å3 |
Mr = 271.35 | Z = 4 |
Orthorhombic, P212121 | Mo Kα radiation |
a = 5.6128 (10) Å | µ = 0.07 mm−1 |
b = 13.627 (3) Å | T = 294 K |
c = 19.442 (4) Å | 0.24 × 0.20 × 0.10 mm |
Bruker SMART CCD area-detector diffractometer | 1783 independent reflections |
Absorption correction: multi-scan (SADABS; Bruker, 1997) | 1305 reflections with I > 2σ(I) |
Tmin = 0.978, Tmax = 0.993 | Rint = 0.038 |
8438 measured reflections |
R[F2 > 2σ(F2)] = 0.037 | 0 restraints |
wR(F2) = 0.091 | H-atom parameters constrained |
S = 1.05 | Δρmax = 0.11 e Å−3 |
1783 reflections | Δρmin = −0.16 e Å−3 |
191 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 > 2σ(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 | ||
N1 | 0.0935 (3) | 0.63116 (13) | 0.76221 (8) | 0.0475 (4) | |
C1 | 0.2777 (4) | 0.56328 (15) | 0.76494 (11) | 0.0455 (5) | |
C2 | 0.3367 (4) | 0.49680 (17) | 0.81636 (12) | 0.0580 (6) | |
H2 | 0.2489 | 0.4935 | 0.8569 | 0.070* | |
C3 | 0.5296 (5) | 0.43580 (17) | 0.80550 (13) | 0.0648 (7) | |
H3 | 0.5713 | 0.3906 | 0.8392 | 0.078* | |
C4 | 0.6626 (5) | 0.44044 (18) | 0.74546 (13) | 0.0652 (7) | |
H4 | 0.7916 | 0.3984 | 0.7395 | 0.078* | |
C5 | 0.6059 (4) | 0.50639 (16) | 0.69475 (12) | 0.0561 (6) | |
H5 | 0.6961 | 0.5095 | 0.6547 | 0.067* | |
C6 | 0.4117 (4) | 0.56873 (15) | 0.70394 (10) | 0.0442 (5) | |
C7 | 0.2999 (4) | 0.64231 (15) | 0.66166 (10) | 0.0432 (5) | |
C8 | 0.3423 (5) | 0.67858 (16) | 0.59604 (10) | 0.0555 (6) | |
H8 | 0.4713 | 0.6559 | 0.5706 | 0.067* | |
C9 | 0.1921 (5) | 0.74821 (18) | 0.56908 (11) | 0.0643 (7) | |
H9 | 0.2199 | 0.7728 | 0.5252 | 0.077* | |
C10 | 0.0001 (5) | 0.78210 (18) | 0.60663 (12) | 0.0644 (7) | |
H10 | −0.1002 | 0.8287 | 0.5871 | 0.077* | |
C11 | −0.0474 (4) | 0.74901 (16) | 0.67204 (11) | 0.0546 (6) | |
H11 | −0.1760 | 0.7730 | 0.6971 | 0.065* | |
C12 | 0.1038 (4) | 0.67853 (15) | 0.69914 (10) | 0.0437 (5) | |
C13 | −0.0820 (4) | 0.64988 (18) | 0.81569 (11) | 0.0552 (6) | |
H13A | −0.1001 | 0.5910 | 0.8433 | 0.066* | |
H13B | −0.2344 | 0.6633 | 0.7941 | 0.066* | |
C14 | −0.0200 (4) | 0.73422 (16) | 0.86244 (10) | 0.0453 (5) | |
C15 | 0.1841 (4) | 0.73371 (18) | 0.90251 (11) | 0.0567 (6) | |
H15 | 0.2884 | 0.6808 | 0.8997 | 0.068* | |
C16 | 0.2353 (5) | 0.81027 (19) | 0.94640 (12) | 0.0618 (7) | |
H16 | 0.3730 | 0.8076 | 0.9729 | 0.074* | |
C17 | 0.0886 (5) | 0.89026 (17) | 0.95206 (11) | 0.0580 (6) | |
C18 | −0.1143 (5) | 0.89149 (19) | 0.91196 (12) | 0.0671 (7) | |
H18 | −0.2173 | 0.9448 | 0.9147 | 0.081* | |
C19 | −0.1675 (4) | 0.81479 (19) | 0.86770 (11) | 0.0606 (6) | |
H19 | −0.3050 | 0.8177 | 0.8411 | 0.073* | |
C20 | 0.1479 (7) | 0.9737 (2) | 1.00032 (13) | 0.0940 (10) | |
H20A | 0.0644 | 1.0318 | 0.9861 | 0.141* | |
H20B | 0.3163 | 0.9858 | 0.9993 | 0.141* | |
H20C | 0.1005 | 0.9566 | 1.0462 | 0.141* |
U11 | U22 | U33 | U12 | U13 | U23 | |
N1 | 0.0424 (10) | 0.0556 (11) | 0.0444 (9) | −0.0032 (9) | 0.0041 (9) | −0.0005 (8) |
C1 | 0.0480 (12) | 0.0420 (11) | 0.0464 (11) | −0.0078 (10) | −0.0047 (11) | −0.0022 (10) |
C2 | 0.0668 (16) | 0.0522 (13) | 0.0551 (13) | −0.0121 (13) | −0.0043 (13) | 0.0054 (11) |
C3 | 0.0764 (18) | 0.0452 (13) | 0.0727 (17) | −0.0016 (13) | −0.0216 (15) | 0.0081 (13) |
C4 | 0.0682 (17) | 0.0504 (13) | 0.0770 (17) | 0.0106 (13) | −0.0178 (15) | −0.0106 (13) |
C5 | 0.0558 (14) | 0.0553 (13) | 0.0573 (13) | 0.0046 (12) | −0.0044 (13) | −0.0116 (12) |
C6 | 0.0465 (12) | 0.0428 (11) | 0.0431 (11) | −0.0025 (10) | −0.0045 (10) | −0.0085 (9) |
C7 | 0.0471 (12) | 0.0429 (11) | 0.0396 (11) | −0.0036 (10) | −0.0023 (10) | −0.0074 (9) |
C8 | 0.0630 (15) | 0.0614 (14) | 0.0422 (12) | 0.0014 (13) | 0.0039 (11) | −0.0051 (11) |
C9 | 0.0849 (18) | 0.0639 (14) | 0.0440 (12) | 0.0068 (16) | −0.0061 (13) | 0.0040 (12) |
C10 | 0.0750 (18) | 0.0607 (16) | 0.0574 (14) | 0.0112 (14) | −0.0205 (14) | −0.0018 (12) |
C11 | 0.0510 (13) | 0.0576 (13) | 0.0550 (13) | 0.0063 (12) | −0.0074 (11) | −0.0120 (12) |
C12 | 0.0435 (11) | 0.0451 (11) | 0.0426 (11) | −0.0025 (10) | −0.0051 (10) | −0.0067 (10) |
C13 | 0.0449 (12) | 0.0698 (15) | 0.0509 (12) | −0.0123 (12) | 0.0096 (11) | −0.0050 (11) |
C14 | 0.0388 (12) | 0.0586 (14) | 0.0385 (11) | −0.0063 (11) | 0.0084 (10) | 0.0020 (10) |
C15 | 0.0494 (13) | 0.0623 (15) | 0.0583 (13) | 0.0062 (12) | −0.0044 (12) | −0.0037 (12) |
C16 | 0.0570 (15) | 0.0775 (17) | 0.0510 (13) | −0.0062 (14) | −0.0091 (12) | −0.0010 (13) |
C17 | 0.0714 (17) | 0.0572 (14) | 0.0454 (13) | −0.0066 (14) | 0.0088 (13) | 0.0023 (11) |
C18 | 0.0773 (18) | 0.0608 (15) | 0.0631 (15) | 0.0150 (14) | 0.0030 (15) | −0.0013 (13) |
C19 | 0.0494 (14) | 0.0770 (17) | 0.0554 (13) | 0.0119 (13) | −0.0026 (12) | 0.0029 (13) |
C20 | 0.129 (3) | 0.0798 (19) | 0.0731 (17) | −0.019 (2) | 0.009 (2) | −0.0189 (16) |
N1—C12 | 1.387 (3) | C10—H10 | 0.9300 |
N1—C1 | 1.388 (3) | C11—C12 | 1.386 (3) |
N1—C13 | 1.455 (3) | C11—H11 | 0.9300 |
C1—C2 | 1.389 (3) | C13—C14 | 1.506 (3) |
C1—C6 | 1.406 (3) | C13—H13A | 0.9700 |
C2—C3 | 1.382 (3) | C13—H13B | 0.9700 |
C2—H2 | 0.9300 | C14—C19 | 1.379 (3) |
C3—C4 | 1.387 (3) | C14—C15 | 1.386 (3) |
C3—H3 | 0.9300 | C15—C16 | 1.378 (3) |
C4—C5 | 1.371 (3) | C15—H15 | 0.9300 |
C4—H4 | 0.9300 | C16—C17 | 1.371 (3) |
C5—C6 | 1.393 (3) | C16—H16 | 0.9300 |
C5—H5 | 0.9300 | C17—C18 | 1.380 (4) |
C6—C7 | 1.440 (3) | C17—C20 | 1.512 (3) |
C7—C8 | 1.389 (3) | C18—C19 | 1.386 (3) |
C7—C12 | 1.409 (3) | C18—H18 | 0.9300 |
C8—C9 | 1.373 (3) | C19—H19 | 0.9300 |
C8—H8 | 0.9300 | C20—H20A | 0.9600 |
C9—C10 | 1.381 (3) | C20—H20B | 0.9600 |
C9—H9 | 0.9300 | C20—H20C | 0.9600 |
C10—C11 | 1.375 (3) | ||
C12—N1—C1 | 108.24 (17) | C12—C11—H11 | 121.3 |
C12—N1—C13 | 125.33 (18) | C11—C12—N1 | 129.3 (2) |
C1—N1—C13 | 126.43 (18) | C11—C12—C7 | 121.63 (19) |
N1—C1—C2 | 129.8 (2) | N1—C12—C7 | 109.06 (18) |
N1—C1—C6 | 109.32 (18) | N1—C13—C14 | 114.12 (18) |
C2—C1—C6 | 120.9 (2) | N1—C13—H13A | 108.7 |
C3—C2—C1 | 118.0 (2) | C14—C13—H13A | 108.7 |
C3—C2—H2 | 121.0 | N1—C13—H13B | 108.7 |
C1—C2—H2 | 121.0 | C14—C13—H13B | 108.7 |
C2—C3—C4 | 121.5 (2) | H13A—C13—H13B | 107.6 |
C2—C3—H3 | 119.2 | C19—C14—C15 | 117.3 (2) |
C4—C3—H3 | 119.2 | C19—C14—C13 | 120.9 (2) |
C5—C4—C3 | 120.7 (2) | C15—C14—C13 | 121.8 (2) |
C5—C4—H4 | 119.7 | C16—C15—C14 | 121.1 (2) |
C3—C4—H4 | 119.7 | C16—C15—H15 | 119.4 |
C4—C5—C6 | 119.3 (2) | C14—C15—H15 | 119.4 |
C4—C5—H5 | 120.4 | C17—C16—C15 | 121.8 (2) |
C6—C5—H5 | 120.4 | C17—C16—H16 | 119.1 |
C5—C6—C1 | 119.6 (2) | C15—C16—H16 | 119.1 |
C5—C6—C7 | 133.8 (2) | C16—C17—C18 | 117.4 (2) |
C1—C6—C7 | 106.56 (18) | C16—C17—C20 | 121.1 (3) |
C8—C7—C12 | 119.0 (2) | C18—C17—C20 | 121.5 (3) |
C8—C7—C6 | 134.2 (2) | C17—C18—C19 | 121.3 (2) |
C12—C7—C6 | 106.79 (17) | C17—C18—H18 | 119.4 |
C9—C8—C7 | 119.4 (2) | C19—C18—H18 | 119.4 |
C9—C8—H8 | 120.3 | C14—C19—C18 | 121.1 (2) |
C7—C8—H8 | 120.3 | C14—C19—H19 | 119.4 |
C8—C9—C10 | 120.5 (2) | C18—C19—H19 | 119.4 |
C8—C9—H9 | 119.7 | C17—C20—H20A | 109.5 |
C10—C9—H9 | 119.7 | C17—C20—H20B | 109.5 |
C11—C10—C9 | 122.0 (2) | H20A—C20—H20B | 109.5 |
C11—C10—H10 | 119.0 | C17—C20—H20C | 109.5 |
C9—C10—H10 | 119.0 | H20A—C20—H20C | 109.5 |
C10—C11—C12 | 117.4 (2) | H20B—C20—H20C | 109.5 |
C10—C11—H11 | 121.3 | ||
C12—N1—C1—C2 | −178.0 (2) | C10—C11—C12—N1 | −178.1 (2) |
C13—N1—C1—C2 | 1.7 (3) | C10—C11—C12—C7 | 0.4 (3) |
C12—N1—C1—C6 | 1.6 (2) | C1—N1—C12—C11 | 177.3 (2) |
C13—N1—C1—C6 | −178.70 (18) | C13—N1—C12—C11 | −2.4 (3) |
N1—C1—C2—C3 | 179.1 (2) | C1—N1—C12—C7 | −1.4 (2) |
C6—C1—C2—C3 | −0.5 (3) | C13—N1—C12—C7 | 178.90 (17) |
C1—C2—C3—C4 | 0.3 (3) | C8—C7—C12—C11 | 0.2 (3) |
C2—C3—C4—C5 | 0.1 (4) | C6—C7—C12—C11 | −178.14 (19) |
C3—C4—C5—C6 | −0.3 (4) | C8—C7—C12—N1 | 178.97 (18) |
C4—C5—C6—C1 | 0.2 (3) | C6—C7—C12—N1 | 0.6 (2) |
C4—C5—C6—C7 | −177.5 (2) | C12—N1—C13—C14 | −84.8 (2) |
N1—C1—C6—C5 | −179.44 (18) | C1—N1—C13—C14 | 95.5 (2) |
C2—C1—C6—C5 | 0.2 (3) | N1—C13—C14—C19 | 119.8 (2) |
N1—C1—C6—C7 | −1.2 (2) | N1—C13—C14—C15 | −61.2 (3) |
C2—C1—C6—C7 | 178.51 (19) | C19—C14—C15—C16 | 0.8 (3) |
C5—C6—C7—C8 | 0.3 (4) | C13—C14—C15—C16 | −178.3 (2) |
C1—C6—C7—C8 | −177.6 (2) | C14—C15—C16—C17 | −0.5 (3) |
C5—C6—C7—C12 | 178.2 (2) | C15—C16—C17—C18 | 0.1 (3) |
C1—C6—C7—C12 | 0.3 (2) | C15—C16—C17—C20 | −179.8 (2) |
C12—C7—C8—C9 | −0.4 (3) | C16—C17—C18—C19 | 0.0 (4) |
C6—C7—C8—C9 | 177.4 (2) | C20—C17—C18—C19 | 179.9 (2) |
C7—C8—C9—C10 | −0.1 (3) | C15—C14—C19—C18 | −0.7 (3) |
C8—C9—C10—C11 | 0.7 (4) | C13—C14—C19—C18 | 178.3 (2) |
C9—C10—C11—C12 | −0.9 (3) | C17—C18—C19—C14 | 0.3 (4) |
Experimental details
Crystal data | |
Chemical formula | C20H17N |
Mr | 271.35 |
Crystal system, space group | Orthorhombic, P212121 |
Temperature (K) | 294 |
a, b, c (Å) | 5.6128 (10), 13.627 (3), 19.442 (4) |
V (Å3) | 1487.0 (5) |
Z | 4 |
Radiation type | Mo Kα |
µ (mm−1) | 0.07 |
Crystal size (mm) | 0.24 × 0.20 × 0.10 |
Data collection | |
Diffractometer | Bruker SMART CCD area-detector diffractometer |
Absorption correction | Multi-scan (SADABS; Bruker, 1997) |
Tmin, Tmax | 0.978, 0.993 |
No. of measured, independent and observed [I > 2σ(I)] reflections | 8438, 1783, 1305 |
Rint | 0.038 |
(sin θ/λ)max (Å−1) | 0.627 |
Refinement | |
R[F2 > 2σ(F2)], wR(F2), S | 0.037, 0.091, 1.05 |
No. of reflections | 1783 |
No. of parameters | 191 |
H-atom treatment | H-atom parameters constrained |
Δρmax, Δρmin (e Å−3) | 0.11, −0.16 |
Computer programs: SMART (Bruker, 1997), SMART, SAINT (Bruker, 1997), SHELXS97 (Sheldrick, 1997), SHELXL97 (Sheldrick, 1997), SHELXTL (Bruker, 1997), SHELXTL.
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Carbazole derivatives substituted by N-alkylation show useful pharmaceutical properties (Buu-Hoï & Royer, 1950; Harfenist & Joyner, 1983; Caulfield et al., 2002; Harper et al., 2002). In this paper, the structure of 9-(4-methyl-benzyl)-9H-carbazole (I) is reported, which was synthesized by N-alkylation of 1-chloromethyl-4-methyl-benzene with carbazole.
The carbazole ring is essentially planar, with mean deviations of 0.029 Å. The dihedral angle formed between the carbazole ring and methyl benzyl ring is 109 (su?)°.