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In the crystal structure of the title complex, C21H21N, the mol­ecule lies on a twofold rotation axis. The N atom is sp2 hybridized. Comparisons are made with similar compounds in this series.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536805010457/rn6045sup1.cif
Contains datablocks global, I

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536805010457/rn6045Isup2.hkl
Contains datablock I

CCDC reference: 272096

Key indicators

  • Single-crystal X-ray study
  • T = 150 K
  • Mean [sigma](C-C) = 0.003 Å
  • R factor = 0.058
  • wR factor = 0.170
  • Data-to-parameter ratio = 13.9

checkCIF/PLATON results

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Alert level B ABSTM02_ALERT_3_B The ratio of expected to reported Tmax/Tmin(RR') is < 0.75 Tmin and Tmax reported: 0.609 0.990 Tmin' and Tmax expected: 0.958 0.989 RR' = 0.635 Please check that your absorption correction is appropriate. PLAT027_ALERT_3_B _diffrn_reflns_theta_full (too) Low ............ 24.99 Deg. PLAT061_ALERT_3_B Tmax/Tmin Range Test RR' too Large ............. 0.63
Alert level C RINTA01_ALERT_3_C The value of Rint is greater than 0.10 Rint given 0.132 PLAT020_ALERT_3_C The value of Rint is greater than 0.10 ......... 0.13 PLAT031_ALERT_4_C Refined Extinction Parameter within Range ...... 2.67 Sigma PLAT063_ALERT_3_C Crystal Probably too Large for Beam Size ....... 0.63 mm PLAT380_ALERT_4_C Check Incorrectly? Oriented X(sp2)-Methyl Moiety C27
0 ALERT level A = In general: serious problem 3 ALERT level B = Potentially serious problem 5 ALERT level C = Check and explain 0 ALERT level G = General alerts; check 0 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 6 ALERT type 3 Indicator that the structure quality may be low 2 ALERT type 4 Improvement, methodology, query or suggestion

Computing details top

Data collection: COLLECT (Nonius, 1998); cell refinement: DENZO-SMN (Otwinowski & Minor, 1997); data reduction: DENZO-SMN; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: SHELXTL/PC (Sheldrick, 2001); software used to prepare material for publication: SHELXTL/PC.

N,N-Bis-(3-methylphenyl)-N-(4-methylphenyl)amine top
Crystal data top
C21H21NF(000) = 616
Mr = 287.39Dx = 1.176 Mg m3
Orthorhombic, PbcnMo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2n 2abCell parameters from 10862 reflections
a = 16.0767 (12) Åθ = 1.7–27.5°
b = 11.2793 (10) ŵ = 0.07 mm1
c = 8.9528 (5) ÅT = 150 K
V = 1623.4 (2) Å3Cuboid, colourless
Z = 40.63 × 0.25 × 0.17 mm
Data collection top
Nonius KappaCCD area-detector
diffractometer
1435 independent reflections
Radiation source: fine-focus sealed tube922 reflections with I > 2σ[I)
Graphite monochromatorRint = 0.132
φ scans, and ω scans with κ offsetsθmax = 25.0°, θmin = 2.2°
Absorption correction: multi-scan
(SORTAV; Blessing, 1995)
h = 1919
Tmin = 0.609, Tmax = 0.990k = 1313
16719 measured reflectionsl = 1010
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)] = 0.058H-atom parameters constrained
wR(F2) = 0.170 w = 1/[σ2(Fo2) + (0.0936P)2 + 0.0289P]
where P = (Fo2 + 2Fc2)/3
S = 1.06(Δ/σ)max < 0.001
1435 reflectionsΔρmax = 0.17 e Å3
103 parametersΔρmin = 0.20 e Å3
0 restraintsExtinction correction: SHELXL97 (Sheldrick, 1997), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
Primary atom site location: structure-invariant direct methodsExtinction coefficient: 0.008 (3)
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)
N100.50000.4939 (2)0.25000.0396 (8)
C110.50000.3668 (3)0.25000.0336 (8)
C120.44856 (13)0.3042 (2)0.1543 (3)0.0379 (7)
H12A0.41310.34560.08740.045*
C130.44864 (14)0.1818 (2)0.1557 (3)0.0421 (7)
H13A0.41240.14040.09000.050*
C140.50000.1174 (3)0.25000.0405 (9)
C150.50000.0161 (3)0.25000.0585 (11)
H15A0.54030.04510.32360.088*0.50
H15B0.51530.04510.15050.088*0.50
H15C0.44440.04510.27590.088*0.50
C210.57671 (13)0.5543 (2)0.2350 (3)0.0353 (6)
C220.64045 (14)0.5059 (2)0.1507 (2)0.0359 (6)
H22A0.63210.43150.10330.043*
C230.71658 (14)0.5637 (2)0.1338 (3)0.0366 (7)
C240.72755 (15)0.6726 (2)0.2011 (3)0.0438 (7)
H24A0.77850.71420.18880.053*
C250.66459 (16)0.7212 (2)0.2864 (3)0.0476 (7)
H25A0.67300.79600.33280.057*
C260.58979 (15)0.6634 (2)0.3054 (3)0.0416 (7)
H26A0.54750.69740.36590.050*
C270.78406 (15)0.5068 (2)0.0414 (3)0.0502 (8)
H27A0.83310.55830.04000.075*
H27B0.76400.49500.06080.075*
H27C0.79900.43000.08510.075*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
N100.0326 (16)0.0235 (18)0.0626 (18)0.0000.0064 (13)0.000
C110.0341 (18)0.027 (2)0.0402 (18)0.0000.0045 (14)0.000
C120.0355 (14)0.0329 (16)0.0451 (13)0.0018 (11)0.0035 (11)0.0029 (11)
C130.0380 (14)0.0349 (18)0.0533 (15)0.0055 (12)0.0005 (11)0.0082 (12)
C140.0338 (19)0.031 (2)0.057 (2)0.0000.0107 (16)0.000
C150.059 (3)0.028 (3)0.089 (3)0.0000.015 (2)0.000
C210.0370 (14)0.0278 (16)0.0409 (13)0.0011 (11)0.0019 (10)0.0034 (11)
C220.0398 (14)0.0283 (16)0.0396 (13)0.0009 (11)0.0027 (11)0.0012 (10)
C230.0370 (14)0.0328 (17)0.0401 (13)0.0009 (11)0.0028 (10)0.0090 (11)
C240.0405 (15)0.0342 (18)0.0566 (16)0.0082 (12)0.0044 (12)0.0072 (12)
C250.0563 (17)0.0284 (17)0.0581 (16)0.0067 (13)0.0067 (13)0.0043 (12)
C260.0482 (15)0.0304 (17)0.0461 (15)0.0008 (12)0.0039 (11)0.0034 (11)
C270.0452 (16)0.046 (2)0.0599 (17)0.0017 (13)0.0078 (13)0.0110 (14)
Geometric parameters (Å, º) top
N10—C21i1.415 (3)C21—C221.385 (3)
N10—C211.415 (3)C21—C261.399 (3)
N10—C111.433 (4)C22—C231.395 (3)
C11—C121.384 (3)C22—H22A0.9500
C11—C12i1.384 (3)C23—C241.379 (4)
C12—C131.381 (3)C23—C271.508 (3)
C12—H12A0.9500C24—C251.381 (3)
C13—C141.386 (3)C24—H24A0.9500
C13—H13A0.9500C25—C261.379 (3)
C14—C13i1.386 (3)C25—H25A0.9500
C14—C151.507 (5)C26—H26A0.9500
C15—H15A0.9800C27—H27A0.9800
C15—H15B0.9800C27—H27B0.9800
C15—H15C0.9800C27—H27C0.9800
C21i—N10—C21122.4 (3)C26—C21—N10120.8 (2)
C21i—N10—C11118.78 (14)C21—C22—C23121.6 (2)
C21—N10—C11118.78 (14)C21—C22—H22A119.2
C12—C11—C12i118.7 (3)C23—C22—H22A119.2
C12—C11—N10120.67 (16)C24—C23—C22118.7 (2)
C12i—C11—N10120.68 (16)C24—C23—C27121.8 (2)
C13—C12—C11120.3 (2)C22—C23—C27119.5 (2)
C13—C12—H12A119.9C23—C24—C25120.1 (2)
C11—C12—H12A119.9C23—C24—H24A120.0
C12—C13—C14122.0 (2)C25—C24—H24A120.0
C12—C13—H13A119.0C26—C25—C24121.3 (3)
C14—C13—H13A119.0C26—C25—H25A119.3
C13i—C14—C13116.9 (3)C24—C25—H25A119.3
C13i—C14—C15121.57 (17)C25—C26—C21119.5 (2)
C13—C14—C15121.57 (17)C25—C26—H26A120.3
C14—C15—H15A109.5C21—C26—H26A120.3
C14—C15—H15B109.5C23—C27—H27A109.5
H15A—C15—H15B109.5C23—C27—H27B109.5
C14—C15—H15C109.5H27A—C27—H27B109.5
H15A—C15—H15C109.5C23—C27—H27C109.5
H15B—C15—H15C109.5H27A—C27—H27C109.5
C22—C21—C26118.8 (2)H27B—C27—H27C109.5
C22—C21—N10120.4 (2)
C21i—N10—C11—C1252.24 (16)C11—N10—C21—C26147.28 (18)
C21—N10—C11—C12127.76 (16)C26—C21—C22—C230.5 (4)
C21i—N10—C11—C12i127.76 (16)N10—C21—C22—C23179.85 (18)
C21—N10—C11—C12i52.24 (16)C21—C22—C23—C241.1 (3)
C12i—C11—C12—C130.36 (15)C21—C22—C23—C27179.7 (2)
N10—C11—C12—C13179.64 (15)C22—C23—C24—C251.6 (3)
C11—C12—C13—C140.7 (3)C27—C23—C24—C25179.2 (2)
C12—C13—C14—C13i0.37 (16)C23—C24—C25—C260.5 (4)
C12—C13—C14—C15179.63 (16)C24—C25—C26—C211.1 (4)
C21i—N10—C21—C22147.6 (2)C22—C21—C26—C251.6 (4)
C11—N10—C21—C2232.3 (2)N10—C21—C26—C25178.8 (2)
C21i—N10—C21—C2632.73 (18)
Symmetry code: (i) x+1, y, z+1/2.
 

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