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The crystal structure of the title complex, C21H21N, consists of discrete mol­ecules with unremarkable geometry. The N atom is sp2-hybridized. Comparisons are made with other aryl­amine mol­ecules.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536804028247/lh6300sup1.cif
Contains datablocks global, I

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536804028247/lh6300Isup2.hkl
Contains datablock I

CCDC reference: 259570

Key indicators

  • Single-crystal X-ray study
  • T = 296 K
  • Mean [sigma](C-C) = 0.005 Å
  • R factor = 0.065
  • wR factor = 0.220
  • Data-to-parameter ratio = 14.7

checkCIF/PLATON results

No syntax errors found



Alert level C ABSTM02_ALERT_3_C The ratio of expected to reported Tmax/Tmin(RR') is < 0.90 Tmin and Tmax reported: 0.837 1.000 Tmin' and Tmax expected: 0.975 0.998 RR' = 0.857 Please check that your absorption correction is appropriate. RINTA01_ALERT_3_C The value of Rint is greater than 0.10 Rint given 0.108 PLAT020_ALERT_3_C The value of Rint is greater than 0.10 ......... 0.11 PLAT026_ALERT_3_C Ratio Observed / Unique Reflections too Low .... 42 Perc. PLAT061_ALERT_3_C Tmax/Tmin Range Test RR' too Large ............. 0.86 PLAT242_ALERT_2_C Check Low U(eq) as Compared to Neighbors for C13 PLAT242_ALERT_2_C Check Low U(eq) as Compared to Neighbors for C33 PLAT340_ALERT_3_C Low Bond Precision on C-C bonds (x 1000) Ang ... 5
0 ALERT level A = In general: serious problem 0 ALERT level B = Potentially serious problem 8 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 2 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 0 ALERT type 4 Improvement, methodology, query or suggestion

Computing details top

Data collection: COLLECT (Nonius, 1997–2001); 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,N-Tris(3-methylphenyl)amine top
Crystal data top
C21H21NF(000) = 1232
Mr = 287.39Dx = 1.138 Mg m3
Orthorhombic, PbcaMo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ac 2abCell parameters from 15740 reflections
a = 18.8439 (13) Åθ = 1.7–26.4°
b = 16.3922 (9) ŵ = 0.07 mm1
c = 10.8561 (7) ÅT = 296 K
V = 3353.4 (4) Å3Plate, colourless
Z = 80.38 × 0.25 × 0.03 mm
Data collection top
Nonius KappaCCD
diffractometer
2947 independent reflections
Radiation source: fine-focus sealed tube1238 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.108
φ scans, and ω scans with κ offsetsθmax = 25.0°, θmin = 2.2°
Absorption correction: multi-scan
(SORTAV; Blessing, 1995)
h = 1922
Tmin = 0.837, Tmax = 1.000k = 1919
37114 measured reflectionsl = 1212
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)] = 0.066H-atom parameters constrained
wR(F2) = 0.220 w = 1/[σ2(Fo2) + (0.1088P)2 + 0.0808P]
where P = (Fo2 + 2Fc2)/3
S = 1.00(Δ/σ)max < 0.001
2947 reflectionsΔρmax = 0.13 e Å3
200 parametersΔρmin = 0.14 e Å3
0 restraintsExtinction correction: SHELXTL/PC, Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
Primary atom site location: structure-invariant direct methodsExtinction coefficient: 0.0070 (14)
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*/Ueq
N100.03547 (14)0.00214 (15)0.2814 (3)0.0878 (10)
C110.03722 (18)0.00132 (19)0.2432 (4)0.0775 (10)
C120.08617 (19)0.04714 (19)0.3027 (3)0.0765 (10)
H12A0.07140.07970.36790.092*
C130.15698 (19)0.0485 (2)0.2677 (4)0.0773 (10)
C140.1769 (2)0.0007 (2)0.1692 (4)0.0939 (12)
H14A0.22390.00110.14290.113*
C150.1283 (2)0.0476 (2)0.1095 (4)0.1063 (14)
H15A0.14280.07980.04350.128*
C160.0584 (2)0.0489 (2)0.1464 (4)0.0975 (13)
H16A0.02580.08180.10570.117*
C170.2098 (2)0.0992 (3)0.3378 (4)0.1091 (14)
H17A0.25600.09260.30190.164*
H17B0.19620.15560.33400.164*
H17C0.21100.08180.42210.164*
C210.07198 (17)0.0713 (2)0.3067 (3)0.0747 (10)
C220.11950 (18)0.0768 (2)0.4024 (3)0.0729 (10)
H22A0.12740.03120.45150.088*
C230.15579 (18)0.1480 (2)0.4277 (4)0.0799 (11)
C240.1431 (2)0.2152 (2)0.3554 (5)0.1008 (13)
H24A0.16670.26390.37150.121*
C250.0956 (2)0.2111 (2)0.2596 (4)0.1079 (15)
H25A0.08740.25700.21140.130*
C260.0600 (2)0.1395 (2)0.2341 (4)0.0945 (12)
H26A0.02830.13700.16860.113*
C270.2068 (2)0.1518 (2)0.5343 (4)0.1080 (14)
H27A0.22740.20520.53860.162*
H27B0.24360.11200.52270.162*
H27C0.18180.14050.60950.162*
C310.06899 (18)0.0779 (2)0.3078 (3)0.0739 (10)
C320.03858 (17)0.1339 (2)0.3869 (3)0.0731 (10)
H32A0.00590.12320.42030.088*
C330.0733 (2)0.2060 (2)0.4173 (3)0.0758 (10)
C340.1374 (2)0.2211 (2)0.3643 (4)0.0925 (12)
H34A0.16030.27000.38160.111*
C350.1693 (2)0.1663 (3)0.2860 (4)0.1037 (13)
H35A0.21380.17730.25300.124*
C360.1344 (2)0.0948 (2)0.2570 (4)0.0892 (12)
H36A0.15520.05780.20300.107*
C370.0416 (2)0.2631 (2)0.5113 (4)0.1144 (15)
H37A0.07190.30980.52110.172*
H37B0.00440.28060.48400.172*
H37C0.03710.23540.58880.172*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
N100.065 (2)0.0670 (18)0.132 (3)0.0031 (16)0.0269 (18)0.0003 (18)
C110.071 (3)0.071 (2)0.090 (3)0.0002 (19)0.015 (2)0.001 (2)
C120.072 (3)0.075 (2)0.082 (2)0.0033 (19)0.010 (2)0.0050 (19)
C130.069 (3)0.076 (2)0.087 (3)0.0011 (19)0.006 (2)0.007 (2)
C140.072 (3)0.096 (3)0.114 (3)0.001 (2)0.027 (2)0.007 (3)
C150.101 (4)0.101 (3)0.117 (4)0.003 (3)0.042 (3)0.019 (3)
C160.095 (3)0.090 (3)0.107 (3)0.014 (2)0.020 (3)0.027 (2)
C170.080 (3)0.128 (3)0.120 (4)0.017 (2)0.002 (3)0.003 (3)
C210.056 (2)0.073 (2)0.096 (3)0.0016 (17)0.003 (2)0.001 (2)
C220.060 (2)0.072 (2)0.087 (3)0.0004 (17)0.001 (2)0.0021 (18)
C230.060 (2)0.084 (3)0.096 (3)0.000 (2)0.006 (2)0.007 (2)
C240.079 (3)0.077 (3)0.147 (4)0.007 (2)0.001 (3)0.001 (3)
C250.085 (3)0.093 (3)0.146 (4)0.008 (2)0.005 (3)0.040 (3)
C260.082 (3)0.089 (3)0.113 (3)0.009 (2)0.015 (2)0.023 (2)
C270.088 (3)0.124 (3)0.113 (3)0.016 (2)0.009 (3)0.025 (3)
C310.059 (2)0.072 (2)0.091 (3)0.0011 (18)0.008 (2)0.007 (2)
C320.056 (2)0.080 (2)0.083 (3)0.0031 (18)0.0007 (19)0.009 (2)
C330.074 (3)0.077 (2)0.076 (2)0.004 (2)0.009 (2)0.0044 (19)
C340.086 (3)0.084 (3)0.107 (3)0.021 (2)0.006 (3)0.007 (2)
C350.079 (3)0.102 (3)0.129 (4)0.020 (2)0.021 (3)0.000 (3)
C360.075 (3)0.090 (3)0.102 (3)0.002 (2)0.011 (2)0.006 (2)
C370.132 (4)0.106 (3)0.106 (3)0.019 (3)0.010 (3)0.018 (3)
Geometric parameters (Å, º) top
N10—C211.413 (4)C24—C251.373 (5)
N10—C311.422 (4)C24—H24A0.9300
N10—C111.431 (4)C25—C261.380 (5)
C11—C161.368 (5)C25—H25A0.9300
C11—C121.378 (4)C26—H26A0.9300
C12—C131.388 (4)C27—H27A0.9600
C12—H12A0.9300C27—H27B0.9600
C13—C141.378 (5)C27—H27C0.9600
C13—C171.504 (5)C31—C361.379 (5)
C14—C151.374 (5)C31—C321.381 (4)
C14—H14A0.9300C32—C331.391 (4)
C15—C161.377 (5)C32—H32A0.9300
C15—H15A0.9300C33—C341.361 (5)
C16—H16A0.9300C33—C371.508 (5)
C17—H17A0.9600C34—C351.375 (5)
C17—H17B0.9600C34—H34A0.9300
C17—H17C0.9600C35—C361.380 (5)
C21—C221.375 (4)C35—H35A0.9300
C21—C261.386 (4)C36—H36A0.9300
C22—C231.381 (4)C37—H37A0.9600
C22—H22A0.9300C37—H37B0.9600
C23—C241.373 (5)C37—H37C0.9600
C23—C271.505 (5)
C21—N10—C31119.2 (3)C25—C24—H24A119.8
C21—N10—C11120.9 (3)C24—C25—C26120.7 (4)
C31—N10—C11119.4 (3)C24—C25—H25A119.6
C16—C11—C12119.5 (3)C26—C25—H25A119.6
C16—C11—N10119.8 (3)C25—C26—C21119.5 (4)
C12—C11—N10120.7 (3)C25—C26—H26A120.2
C11—C12—C13121.7 (3)C21—C26—H26A120.2
C11—C12—H12A119.2C23—C27—H27A109.5
C13—C12—H12A119.2C23—C27—H27B109.5
C14—C13—C12117.7 (3)H27A—C27—H27B109.5
C14—C13—C17121.8 (4)C23—C27—H27C109.5
C12—C13—C17120.5 (3)H27A—C27—H27C109.5
C15—C14—C13120.8 (4)H27B—C27—H27C109.5
C15—C14—H14A119.6C36—C31—C32119.1 (3)
C13—C14—H14A119.6C36—C31—N10119.5 (3)
C14—C15—C16120.6 (4)C32—C31—N10121.4 (3)
C14—C15—H15A119.7C31—C32—C33121.2 (3)
C16—C15—H15A119.7C31—C32—H32A119.4
C11—C16—C15119.6 (4)C33—C32—H32A119.4
C11—C16—H16A120.2C34—C33—C32118.1 (3)
C15—C16—H16A120.2C34—C33—C37121.6 (4)
C13—C17—H17A109.5C32—C33—C37120.2 (4)
C13—C17—H17B109.5C33—C34—C35122.0 (3)
H17A—C17—H17B109.5C33—C34—H34A119.0
C13—C17—H17C109.5C35—C34—H34A119.0
H17A—C17—H17C109.5C34—C35—C36119.2 (4)
H17B—C17—H17C109.5C34—C35—H35A120.4
C22—C21—C26118.9 (3)C36—C35—H35A120.4
C22—C21—N10121.3 (3)C31—C36—C35120.3 (4)
C26—C21—N10119.8 (3)C31—C36—H36A119.8
C21—C22—C23121.9 (3)C35—C36—H36A119.8
C21—C22—H22A119.0C33—C37—H37A109.5
C23—C22—H22A119.0C33—C37—H37B109.5
C24—C23—C22118.5 (4)H37A—C37—H37B109.5
C24—C23—C27121.2 (4)C33—C37—H37C109.5
C22—C23—C27120.2 (4)H37A—C37—H37C109.5
C23—C24—C25120.4 (4)H37B—C37—H37C109.5
C23—C24—H24A119.8
C21—N10—C11—C16134.4 (4)C21—C22—C23—C27179.3 (3)
C31—N10—C11—C1652.8 (5)C22—C23—C24—C250.5 (6)
C21—N10—C11—C1245.4 (5)C27—C23—C24—C25179.1 (4)
C31—N10—C11—C12127.4 (4)C23—C24—C25—C260.1 (6)
C16—C11—C12—C130.6 (5)C24—C25—C26—C210.6 (6)
N10—C11—C12—C13179.6 (3)C22—C21—C26—C250.3 (6)
C11—C12—C13—C141.2 (5)N10—C21—C26—C25179.7 (4)
C11—C12—C13—C17177.3 (3)C21—N10—C31—C3655.8 (5)
C12—C13—C14—C151.0 (5)C11—N10—C31—C36131.3 (4)
C17—C13—C14—C15177.4 (4)C21—N10—C31—C32121.8 (4)
C13—C14—C15—C160.4 (6)C11—N10—C31—C3251.1 (5)
C12—C11—C16—C150.1 (6)C36—C31—C32—C331.0 (5)
N10—C11—C16—C15179.7 (4)N10—C31—C32—C33176.7 (3)
C14—C15—C16—C110.2 (6)C31—C32—C33—C341.8 (5)
C31—N10—C21—C2231.2 (5)C31—C32—C33—C37175.3 (3)
C11—N10—C21—C22141.7 (3)C32—C33—C34—C352.3 (6)
C31—N10—C21—C26148.8 (4)C37—C33—C34—C35174.7 (4)
C11—N10—C21—C2638.4 (5)C33—C34—C35—C362.0 (6)
C26—C21—C22—C230.3 (5)C32—C31—C36—C350.7 (5)
N10—C21—C22—C23179.7 (3)N10—C31—C36—C35177.0 (3)
C21—C22—C23—C240.7 (5)C34—C35—C36—C311.2 (6)
 

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