Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536807054402/cv2328sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S1600536807054402/cv2328Isup2.hkl |
CCDC reference: 672833
Key indicators
- Single-crystal X-ray study
- T = 293 K
- Mean (C-C) = 0.004 Å
- R factor = 0.069
- wR factor = 0.160
- Data-to-parameter ratio = 14.6
checkCIF/PLATON results
No syntax errors found
Alert level C PLAT066_ALERT_1_C Predicted and Reported Transmissions Identical . ? PLAT125_ALERT_4_C No _symmetry_space_group_name_Hall Given ....... ? PLAT241_ALERT_2_C Check High Ueq as Compared to Neighbors for C6 PLAT241_ALERT_2_C Check High Ueq as Compared to Neighbors for C13 PLAT242_ALERT_2_C Check Low Ueq as Compared to Neighbors for C9
Alert level G PLAT199_ALERT_1_G Check the Reported _cell_measurement_temperature 293 K PLAT200_ALERT_1_G Check the Reported _diffrn_ambient_temperature . 293 K
0 ALERT level A = In general: serious problem 0 ALERT level B = Potentially serious problem 5 ALERT level C = Check and explain 2 ALERT level G = General alerts; check 3 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 0 ALERT type 3 Indicator that the structure quality may be low 1 ALERT type 4 Improvement, methodology, query or suggestion 0 ALERT type 5 Informative message, check
Bi et al. (2007) have reported the crystal structure of polymorph (I). For related crystal structures, see also Ianelli et al. (1993).
All manipulations were carried out under argon or in vacuo using standard Schlenk techniques. n-Butyllithium(3 ml,1.7M in Hexane) was added dropwise to a solution of N-benzyl phenyl amine(0.92 g, 5 mmol) in hexane at 273 K, and then the temperature was allowed to rise to room temperature. The mixture was stirred for further 5 h and then simply add benzyl chloride(0.63 g, 5 mmol) to it at 273 K. The mixture was warmed slowly to room temperaturethe solution, and was stirred for further 5 h at room temperature. Then the solvent was removed under vacuum and ether was used to extract the solid. The filtrate was concentrated under a vacuum until colourless crystals of the title compound appeared(1.12 g, yield 82%), suitable for X-ray analysis. Elemental analysis, found: C 87.90, H 6.98, N 5.12%; calculated: C 87.87, H 7.01, N 5.12%.
All H atoms were positioned geometrically (C—H = 0.93–0.97 A°) and refined as riding, with Uiso(H) = 1.2Ueq(C).
Data collection: SMART (Siemens, 1996); cell refinement: SAINT (Siemens, 1996); data reduction: SAINT (Siemens, 1996); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEP-3 (Farrugia, 1997); software used to prepare material for publication: SHELXL97 (Sheldrick, 1997).
Fig. 1. The asymmetric unit of (II), showing the atom-labelling scheme and displacement ellipsoids drawn at the 50% probability level. |
C20H19N | F(000) = 584 |
Mr = 273.36 | Dx = 1.145 Mg m−3 |
Monoclinic, P21/n | Mo Kα radiation, λ = 0.71073 Å |
a = 8.061 (4) Å | Cell parameters from 1210 reflections |
b = 11.529 (6) Å | θ = 2.4–20.0° |
c = 17.065 (9) Å | µ = 0.07 mm−1 |
β = 91.245 (13)° | T = 293 K |
V = 1585.6 (14) Å3 | Block, colourless |
Z = 4 | 0.30 × 0.20 × 0.20 mm |
Siemens SMART CCD area detector diffractometer | 2797 independent reflections |
Radiation source: fine-focus sealed tube | 1858 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.035 |
ω scans | θmax = 25.0°, θmin = 2.1° |
Absorption correction: multi-scan (SADABS; Sheldrick, 1996) | h = −9→7 |
Tmin = 0.981, Tmax = 0.987 | k = −13→13 |
6429 measured reflections | l = −20→20 |
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)] = 0.069 | H-atom parameters constrained |
wR(F2) = 0.160 | w = 1/[σ2(Fo2) + (0.0581P)2 + 0.3456P] where P = (Fo2 + 2Fc2)/3 |
S = 1.08 | (Δ/σ)max < 0.001 |
2797 reflections | Δρmax = 0.22 e Å−3 |
191 parameters | Δρmin = −0.16 e Å−3 |
0 restraints | Extinction correction: SHELXL, Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4 |
Primary atom site location: structure-invariant direct methods | Extinction coefficient: 0.014 (2) |
C20H19N | V = 1585.6 (14) Å3 |
Mr = 273.36 | Z = 4 |
Monoclinic, P21/n | Mo Kα radiation |
a = 8.061 (4) Å | µ = 0.07 mm−1 |
b = 11.529 (6) Å | T = 293 K |
c = 17.065 (9) Å | 0.30 × 0.20 × 0.20 mm |
β = 91.245 (13)° |
Siemens SMART CCD area detector diffractometer | 2797 independent reflections |
Absorption correction: multi-scan (SADABS; Sheldrick, 1996) | 1858 reflections with I > 2σ(I) |
Tmin = 0.981, Tmax = 0.987 | Rint = 0.035 |
6429 measured reflections |
R[F2 > 2σ(F2)] = 0.069 | 0 restraints |
wR(F2) = 0.160 | H-atom parameters constrained |
S = 1.08 | Δρmax = 0.22 e Å−3 |
2797 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 > 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 | ||
N1 | 0.0735 (3) | 0.06758 (18) | 0.13394 (12) | 0.0613 (6) | |
C1 | 0.0455 (3) | 0.1689 (2) | 0.08584 (15) | 0.0666 (7) | |
H1A | −0.0572 | 0.2050 | 0.1017 | 0.080* | |
H1B | 0.0298 | 0.1438 | 0.0319 | 0.080* | |
C2 | 0.1806 (3) | 0.2599 (2) | 0.08834 (14) | 0.0599 (7) | |
C3 | 0.3256 (4) | 0.2461 (3) | 0.13071 (16) | 0.0709 (8) | |
H3 | 0.3447 | 0.1785 | 0.1593 | 0.085* | |
C4 | 0.4449 (4) | 0.3343 (3) | 0.13072 (17) | 0.0867 (10) | |
H4 | 0.5439 | 0.3259 | 0.1592 | 0.104* | |
C5 | 0.4141 (6) | 0.4338 (3) | 0.0881 (2) | 0.0968 (12) | |
H5 | 0.4923 | 0.4930 | 0.0882 | 0.116* | |
C6 | 0.2711 (6) | 0.4459 (3) | 0.0461 (2) | 0.1071 (12) | |
H6 | 0.2520 | 0.5129 | 0.0170 | 0.129* | |
C7 | 0.1555 (4) | 0.3605 (3) | 0.04629 (17) | 0.0822 (9) | |
H7 | 0.0573 | 0.3701 | 0.0174 | 0.099* | |
C8 | 0.0270 (3) | 0.0789 (2) | 0.21503 (15) | 0.0675 (8) | |
H8A | 0.0513 | 0.1575 | 0.2320 | 0.081* | |
H8B | 0.0962 | 0.0272 | 0.2464 | 0.081* | |
C9 | −0.1526 (3) | 0.0532 (2) | 0.23217 (14) | 0.0563 (6) | |
C10 | −0.2459 (3) | −0.0233 (2) | 0.18791 (15) | 0.0682 (7) | |
H10 | −0.1999 | −0.0574 | 0.1440 | 0.082* | |
C11 | −0.4059 (4) | −0.0501 (3) | 0.20734 (19) | 0.0842 (9) | |
H11 | −0.4673 | −0.1020 | 0.1767 | 0.101* | |
C12 | −0.4743 (4) | −0.0010 (4) | 0.2713 (2) | 0.0988 (12) | |
H12 | −0.5820 | −0.0201 | 0.2850 | 0.119* | |
C13 | −0.3849 (5) | 0.0764 (4) | 0.3155 (2) | 0.1083 (12) | |
H13 | −0.4319 | 0.1104 | 0.3592 | 0.130* | |
C14 | −0.2251 (4) | 0.1041 (3) | 0.29547 (17) | 0.0821 (9) | |
H14 | −0.1656 | 0.1581 | 0.3252 | 0.099* | |
C15 | 0.1611 (3) | −0.0270 (2) | 0.10677 (14) | 0.0551 (6) | |
C16 | 0.2536 (3) | −0.0206 (2) | 0.03909 (14) | 0.0604 (7) | |
H16 | 0.2576 | 0.0490 | 0.0117 | 0.073* | |
C17 | 0.3388 (3) | −0.1146 (3) | 0.01189 (16) | 0.0702 (8) | |
H17 | 0.3989 | −0.1077 | −0.0338 | 0.084* | |
C18 | 0.3372 (4) | −0.2186 (3) | 0.05075 (19) | 0.0763 (8) | |
H18 | 0.3965 | −0.2818 | 0.0324 | 0.092* | |
C19 | 0.2454 (4) | −0.2270 (3) | 0.11777 (18) | 0.0750 (8) | |
H19 | 0.2421 | −0.2973 | 0.1445 | 0.090* | |
C20 | 0.1585 (3) | −0.1337 (2) | 0.14601 (15) | 0.0647 (7) | |
H20 | 0.0977 | −0.1416 | 0.1914 | 0.078* |
U11 | U22 | U33 | U12 | U13 | U23 | |
N1 | 0.0607 (14) | 0.0637 (14) | 0.0599 (13) | −0.0101 (11) | 0.0090 (10) | 0.0072 (11) |
C1 | 0.0600 (17) | 0.0689 (17) | 0.0708 (17) | −0.0068 (14) | 0.0003 (13) | 0.0072 (14) |
C2 | 0.0665 (18) | 0.0565 (15) | 0.0572 (16) | −0.0084 (13) | 0.0077 (13) | −0.0049 (12) |
C3 | 0.0702 (19) | 0.0755 (19) | 0.0674 (17) | −0.0185 (16) | 0.0059 (14) | −0.0090 (14) |
C4 | 0.081 (2) | 0.111 (3) | 0.0683 (19) | −0.031 (2) | 0.0109 (16) | −0.030 (2) |
C5 | 0.121 (3) | 0.081 (2) | 0.090 (2) | −0.050 (2) | 0.037 (2) | −0.018 (2) |
C6 | 0.139 (4) | 0.074 (2) | 0.109 (3) | −0.028 (3) | 0.021 (3) | 0.005 (2) |
C7 | 0.099 (2) | 0.0647 (19) | 0.083 (2) | −0.0072 (18) | 0.0071 (17) | 0.0064 (16) |
C8 | 0.0644 (18) | 0.0748 (18) | 0.0631 (17) | −0.0161 (14) | −0.0009 (13) | −0.0043 (14) |
C9 | 0.0541 (16) | 0.0624 (16) | 0.0523 (14) | 0.0022 (13) | −0.0016 (12) | 0.0036 (13) |
C10 | 0.0585 (18) | 0.0820 (19) | 0.0640 (17) | −0.0064 (15) | 0.0021 (13) | −0.0050 (15) |
C11 | 0.0551 (19) | 0.108 (2) | 0.090 (2) | −0.0116 (17) | −0.0011 (16) | 0.0071 (19) |
C12 | 0.0516 (19) | 0.154 (3) | 0.091 (2) | 0.007 (2) | 0.0077 (18) | 0.023 (2) |
C13 | 0.067 (2) | 0.176 (4) | 0.083 (2) | 0.031 (2) | 0.0105 (18) | −0.015 (2) |
C14 | 0.069 (2) | 0.099 (2) | 0.078 (2) | 0.0170 (17) | −0.0051 (16) | −0.0199 (17) |
C15 | 0.0493 (15) | 0.0623 (16) | 0.0537 (14) | −0.0189 (13) | −0.0023 (12) | 0.0026 (13) |
C16 | 0.0624 (17) | 0.0643 (16) | 0.0545 (15) | −0.0183 (14) | 0.0000 (13) | 0.0021 (13) |
C17 | 0.0650 (19) | 0.078 (2) | 0.0683 (18) | −0.0194 (15) | 0.0073 (14) | −0.0104 (16) |
C18 | 0.0677 (19) | 0.069 (2) | 0.092 (2) | −0.0075 (15) | −0.0011 (16) | −0.0085 (17) |
C19 | 0.0684 (19) | 0.0638 (19) | 0.092 (2) | −0.0126 (16) | −0.0091 (17) | 0.0166 (16) |
C20 | 0.0570 (17) | 0.0717 (18) | 0.0655 (16) | −0.0185 (15) | 0.0018 (13) | 0.0141 (14) |
N1—C15 | 1.385 (3) | C9—C10 | 1.374 (3) |
N1—C1 | 1.443 (3) | C10—C11 | 1.374 (4) |
N1—C8 | 1.447 (3) | C10—H10 | 0.9300 |
C1—C2 | 1.512 (3) | C11—C12 | 1.358 (4) |
C1—H1A | 0.9700 | C11—H11 | 0.9300 |
C1—H1B | 0.9700 | C12—C13 | 1.365 (5) |
C2—C3 | 1.370 (4) | C12—H12 | 0.9300 |
C2—C7 | 1.377 (4) | C13—C14 | 1.378 (5) |
C3—C4 | 1.400 (4) | C13—H13 | 0.9300 |
C3—H3 | 0.9300 | C14—H14 | 0.9300 |
C4—C5 | 1.378 (5) | C15—C16 | 1.390 (3) |
C4—H4 | 0.9300 | C15—C20 | 1.401 (3) |
C5—C6 | 1.351 (5) | C16—C17 | 1.370 (4) |
C5—H5 | 0.9300 | C16—H16 | 0.9300 |
C6—C7 | 1.355 (5) | C17—C18 | 1.370 (4) |
C6—H6 | 0.9300 | C17—H17 | 0.9300 |
C7—H7 | 0.9300 | C18—C19 | 1.379 (4) |
C8—C9 | 1.513 (3) | C18—H18 | 0.9300 |
C8—H8A | 0.9700 | C19—C20 | 1.376 (4) |
C8—H8B | 0.9700 | C19—H19 | 0.9300 |
C9—C14 | 1.371 (3) | C20—H20 | 0.9300 |
C15—N1—C1 | 121.5 (2) | C10—C9—C8 | 122.3 (2) |
C15—N1—C8 | 122.4 (2) | C9—C10—C11 | 121.2 (3) |
C1—N1—C8 | 115.5 (2) | C9—C10—H10 | 119.4 |
N1—C1—C2 | 116.2 (2) | C11—C10—H10 | 119.4 |
N1—C1—H1A | 108.2 | C12—C11—C10 | 120.0 (3) |
C2—C1—H1A | 108.2 | C12—C11—H11 | 120.0 |
N1—C1—H1B | 108.2 | C10—C11—H11 | 120.0 |
C2—C1—H1B | 108.2 | C11—C12—C13 | 119.9 (3) |
H1A—C1—H1B | 107.4 | C11—C12—H12 | 120.1 |
C3—C2—C7 | 119.1 (3) | C13—C12—H12 | 120.1 |
C3—C2—C1 | 122.7 (2) | C12—C13—C14 | 120.0 (3) |
C7—C2—C1 | 118.2 (3) | C12—C13—H13 | 120.0 |
C2—C3—C4 | 119.6 (3) | C14—C13—H13 | 120.0 |
C2—C3—H3 | 120.2 | C9—C14—C13 | 120.8 (3) |
C4—C3—H3 | 120.2 | C9—C14—H14 | 119.6 |
C5—C4—C3 | 119.2 (3) | C13—C14—H14 | 119.6 |
C5—C4—H4 | 120.4 | N1—C15—C16 | 121.5 (2) |
C3—C4—H4 | 120.4 | N1—C15—C20 | 121.2 (2) |
C6—C5—C4 | 120.6 (3) | C16—C15—C20 | 117.2 (3) |
C6—C5—H5 | 119.7 | C17—C16—C15 | 121.4 (3) |
C4—C5—H5 | 119.7 | C17—C16—H16 | 119.3 |
C5—C6—C7 | 120.2 (4) | C15—C16—H16 | 119.3 |
C5—C6—H6 | 119.9 | C16—C17—C18 | 121.2 (3) |
C7—C6—H6 | 119.9 | C16—C17—H17 | 119.4 |
C6—C7—C2 | 121.3 (3) | C18—C17—H17 | 119.4 |
C6—C7—H7 | 119.3 | C17—C18—C19 | 118.3 (3) |
C2—C7—H7 | 119.3 | C17—C18—H18 | 120.8 |
N1—C8—C9 | 115.9 (2) | C19—C18—H18 | 120.8 |
N1—C8—H8A | 108.3 | C20—C19—C18 | 121.4 (3) |
C9—C8—H8A | 108.3 | C20—C19—H19 | 119.3 |
N1—C8—H8B | 108.3 | C18—C19—H19 | 119.3 |
C9—C8—H8B | 108.3 | C19—C20—C15 | 120.4 (3) |
H8A—C8—H8B | 107.4 | C19—C20—H20 | 119.8 |
C14—C9—C10 | 118.1 (3) | C15—C20—H20 | 119.8 |
C14—C9—C8 | 119.6 (2) |
Experimental details
Crystal data | |
Chemical formula | C20H19N |
Mr | 273.36 |
Crystal system, space group | Monoclinic, P21/n |
Temperature (K) | 293 |
a, b, c (Å) | 8.061 (4), 11.529 (6), 17.065 (9) |
β (°) | 91.245 (13) |
V (Å3) | 1585.6 (14) |
Z | 4 |
Radiation type | Mo Kα |
µ (mm−1) | 0.07 |
Crystal size (mm) | 0.30 × 0.20 × 0.20 |
Data collection | |
Diffractometer | Siemens SMART CCD area detector diffractometer |
Absorption correction | Multi-scan (SADABS; Sheldrick, 1996) |
Tmin, Tmax | 0.981, 0.987 |
No. of measured, independent and observed [I > 2σ(I)] reflections | 6429, 2797, 1858 |
Rint | 0.035 |
(sin θ/λ)max (Å−1) | 0.595 |
Refinement | |
R[F2 > 2σ(F2)], wR(F2), S | 0.069, 0.160, 1.08 |
No. of reflections | 2797 |
No. of parameters | 191 |
H-atom treatment | H-atom parameters constrained |
Δρmax, Δρmin (e Å−3) | 0.22, −0.16 |
Computer programs: SMART (Siemens, 1996), SAINT (Siemens, 1996), SHELXS97 (Sheldrick, 1997), SHELXL97 (Sheldrick, 1997), ORTEP-3 (Farrugia, 1997).
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We report here the crystal structure of the title compound, (II), which is a second polymorph of N,N-dibenzylaniline (Bi et al., 2007) (I).
The asymmetric unit of (II) contains one independent molecule (Fig. 1). The C—N bond lengths in (II) agree with those reported for similar compounds (Ianelli et al., 1993). The molecular conformations in (I) and (II) are is slightly different. In (II), the mean plane N1/C1/C8/C15 makes dihedral angles of 90.5 (1), 98.1 (1), 18.3 (1)° with the phenyl rings C2—C7, C9—C14 and C15—C20, respectively.
In the absence of classical hydrogen bonds, the crystal packing is stabilized by van der Waals forces.