Buy article online - an online subscription or single-article purchase is required to access this article.
Download citation
Download citation
link to html
The title compound, C20H19N, crystallizes with two independent mol­ecules in the asymmetric unit. The conformations of the mol­ecules are slightly different. In the absence of classical hydrogen bonds, the crystal packing is stabilized by van der Waals forces.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536807011476/cv2209sup1.cif
Contains datablocks global, I

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536807011476/cv2209Isup2.hkl
Contains datablock I

CCDC reference: 642961

Key indicators

  • Single-crystal X-ray study
  • T = 293 K
  • Mean [sigma](C-C) = 0.004 Å
  • R factor = 0.057
  • wR factor = 0.148
  • 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 ....... ? PLAT152_ALERT_1_C Supplied and Calc Volume s.u. Inconsistent ..... ? PLAT241_ALERT_2_C Check High Ueq as Compared to Neighbors for C17 PLAT241_ALERT_2_C Check High Ueq as Compared to Neighbors for C39 PLAT242_ALERT_2_C Check Low Ueq as Compared to Neighbors for C8 PLAT242_ALERT_2_C Check Low Ueq as Compared to Neighbors for C15 PLAT242_ALERT_2_C Check Low Ueq as Compared to Neighbors for C28 PLAT242_ALERT_2_C Check Low Ueq as Compared to Neighbors for C35
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 9 ALERT level C = Check and explain 2 ALERT level G = General alerts; check 4 ALERT type 1 CIF construction/syntax error, inconsistent or missing data 6 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

Computing details top

Data collection: SMART (Siemens, 1996); cell refinement: SAINT (Siemens, 1996); data reduction: SAINT; 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.

N,N-Dibenzylaniline top
Crystal data top
C20H19NF(000) = 1168
Mr = 273.36Dx = 1.159 Mg m3
Monoclinic, P21/nMo Kα radiation, λ = 0.71073 Å
a = 11.7514 (16) ÅCell parameters from 1790 reflections
b = 9.0604 (13) Åθ = 2.3–19.5°
c = 29.522 (4) ŵ = 0.07 mm1
β = 94.589 (3)°T = 293 K
V = 3133.2 (7) Å3Block, colourless
Z = 80.30 × 0.20 × 0.20 mm
Data collection top
Siemens SMART CCD area-detector
diffractometer
5517 independent reflections
Radiation source: fine-focus sealed tube3045 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.034
ω scansθmax = 25.0°, θmin = 1.8°
Absorption correction: multi-scan
(SADABS; Sheldrick, 1996)
h = 913
Tmin = 0.980, Tmax = 0.987k = 1010
12653 measured reflectionsl = 3534
Refinement top
Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.057Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.148H-atom parameters constrained
S = 1.02 w = 1/[σ2(Fo2) + (0.0308P)2 + 0.3923P]
where P = (Fo2 + 2Fc2)/3
5517 reflections(Δ/σ)max < 0.001
379 parametersΔρmax = 0.16 e Å3
0 restraintsΔρmin = 0.25 e Å3
Special details top

Experimental. Elemental analysis, found: C 87.90, H 6.98, N 5.12%, calculated: C 87.87, H 7.01, N 5.12%.

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
N10.20492 (16)0.79151 (19)0.33198 (6)0.0674 (5)
C10.2869 (2)0.8091 (2)0.30098 (7)0.0629 (6)
C20.2807 (2)0.7334 (3)0.25946 (8)0.0737 (7)
H20.21970.67030.25210.088*
C30.3633 (3)0.7509 (3)0.22953 (9)0.0862 (8)
H30.35650.69970.20210.103*
C40.4556 (2)0.8416 (3)0.23887 (10)0.0894 (8)
H40.51140.85200.21850.107*
C50.4625 (2)0.9162 (3)0.27926 (10)0.0886 (8)
H50.52380.97950.28620.106*
C60.3814 (2)0.9002 (3)0.30983 (8)0.0768 (7)
H60.38990.95150.33720.092*
C70.1856 (2)0.9054 (2)0.36565 (7)0.0723 (6)
H7A0.10820.94220.36010.087*
H7B0.23720.98710.36160.087*
C80.20287 (19)0.8522 (2)0.41400 (7)0.0598 (5)
C90.1152 (2)0.8538 (3)0.44236 (9)0.0803 (7)
H90.04250.88310.43110.096*
C100.1346 (3)0.8121 (3)0.48776 (10)0.0960 (9)
H100.07500.81370.50670.115*
C110.2411 (3)0.7688 (3)0.50454 (9)0.0976 (9)
H110.25440.74200.53490.117*
C120.3268 (3)0.7651 (3)0.47683 (9)0.0900 (8)
H120.39910.73480.48820.108*
C130.3084 (2)0.8058 (3)0.43195 (8)0.0739 (7)
H130.36860.80180.41340.089*
C140.10810 (19)0.6946 (2)0.32285 (7)0.0717 (6)
H14A0.08530.65750.35160.086*
H14B0.13210.61070.30560.086*
C150.00501 (19)0.7639 (2)0.29713 (7)0.0651 (6)
C160.1020 (3)0.7054 (3)0.30085 (10)0.0986 (9)
H160.11040.62320.31920.118*
C170.1973 (2)0.7677 (4)0.27759 (13)0.1202 (11)
H170.26900.72670.28040.144*
C180.1870 (3)0.8879 (4)0.25085 (10)0.1046 (9)
H180.25110.92930.23520.126*
C190.0818 (2)0.9470 (3)0.24716 (9)0.0917 (8)
H190.07401.03010.22920.110*
C200.0130 (2)0.8849 (3)0.26981 (8)0.0778 (7)
H200.08440.92600.26650.093*
N20.76841 (17)0.6938 (2)0.54883 (7)0.0775 (6)
C210.6865 (2)0.7086 (3)0.57952 (8)0.0726 (7)
C220.6943 (2)0.6304 (3)0.62023 (9)0.0845 (7)
H220.75600.56750.62690.101*
C230.6128 (3)0.6443 (4)0.65075 (10)0.1010 (9)
H230.62020.59100.67770.121*
C240.5213 (3)0.7349 (4)0.64204 (12)0.1090 (10)
H240.46630.74390.66290.131*
C250.5114 (3)0.8129 (3)0.60211 (13)0.1037 (10)
H250.44920.87530.59610.124*
C260.5924 (2)0.8006 (3)0.57053 (10)0.0859 (8)
H260.58380.85360.54350.103*
C270.7755 (2)0.7950 (3)0.51136 (8)0.0838 (7)
H27A0.85510.80550.50540.101*
H27B0.74880.89100.52050.101*
C280.70797 (19)0.7503 (3)0.46755 (8)0.0710 (6)
C290.7174 (3)0.8357 (3)0.42925 (9)0.0969 (8)
H290.76590.91700.43050.116*
C300.6545 (3)0.8003 (4)0.38895 (10)0.1147 (11)
H300.66060.85820.36330.138*
C310.5834 (3)0.6803 (4)0.38689 (11)0.1095 (11)
H310.54090.65730.35990.131*
C320.5750 (2)0.5949 (3)0.42422 (10)0.0945 (8)
H320.52750.51260.42270.113*
C330.6370 (2)0.6303 (3)0.46458 (8)0.0800 (7)
H330.63040.57160.49010.096*
C340.8562 (2)0.5822 (3)0.55406 (8)0.0845 (7)
H34A0.87530.55210.52410.101*
H34B0.82500.49670.56850.101*
C350.9651 (2)0.6275 (3)0.58139 (7)0.0705 (6)
C360.9746 (2)0.7601 (3)0.60403 (8)0.0823 (7)
H360.91230.82370.60270.099*
C371.0740 (2)0.8013 (4)0.62871 (9)0.1014 (9)
H371.07860.89170.64370.122*
C381.1659 (3)0.7084 (6)0.63100 (11)0.1219 (13)
H381.23330.73530.64760.146*
C391.1589 (3)0.5768 (5)0.60900 (14)0.1306 (16)
H391.22150.51370.61050.157*
C401.0585 (3)0.5365 (3)0.58436 (10)0.1032 (10)
H401.05440.44590.56950.124*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
N10.0801 (13)0.0646 (12)0.0560 (11)0.0015 (10)0.0042 (10)0.0082 (9)
C10.0704 (15)0.0581 (14)0.0572 (14)0.0074 (12)0.0129 (12)0.0018 (11)
C20.0785 (17)0.0700 (16)0.0703 (15)0.0062 (12)0.0079 (14)0.0143 (13)
C30.094 (2)0.093 (2)0.0710 (17)0.0245 (17)0.0012 (16)0.0098 (14)
C40.0812 (19)0.102 (2)0.0849 (19)0.0143 (16)0.0051 (15)0.0088 (16)
C50.0810 (19)0.092 (2)0.0900 (19)0.0080 (15)0.0095 (16)0.0104 (17)
C60.0857 (18)0.0802 (17)0.0616 (15)0.0028 (14)0.0113 (14)0.0010 (13)
C70.0874 (17)0.0658 (15)0.0618 (14)0.0104 (12)0.0062 (12)0.0081 (12)
C80.0644 (15)0.0573 (13)0.0571 (13)0.0005 (11)0.0014 (11)0.0069 (10)
C90.0744 (17)0.0745 (16)0.0928 (19)0.0056 (12)0.0127 (15)0.0052 (14)
C100.120 (3)0.088 (2)0.086 (2)0.0196 (18)0.0446 (19)0.0023 (16)
C110.142 (3)0.089 (2)0.0610 (16)0.014 (2)0.006 (2)0.0084 (14)
C120.102 (2)0.096 (2)0.0688 (17)0.0009 (16)0.0119 (16)0.0100 (15)
C130.0747 (16)0.0821 (17)0.0647 (15)0.0043 (13)0.0035 (12)0.0050 (13)
C140.0866 (17)0.0638 (15)0.0639 (14)0.0031 (13)0.0007 (12)0.0022 (11)
C150.0719 (16)0.0639 (14)0.0590 (13)0.0035 (12)0.0014 (11)0.0051 (11)
C160.087 (2)0.0832 (19)0.126 (2)0.0171 (16)0.0092 (18)0.0110 (17)
C170.0648 (19)0.112 (3)0.182 (3)0.0152 (18)0.002 (2)0.002 (2)
C180.086 (2)0.106 (2)0.117 (2)0.0048 (18)0.0219 (18)0.003 (2)
C190.0820 (19)0.101 (2)0.0900 (19)0.0081 (17)0.0026 (15)0.0191 (16)
C200.0683 (16)0.0887 (18)0.0756 (16)0.0028 (13)0.0006 (12)0.0161 (14)
N20.0783 (14)0.0843 (15)0.0673 (13)0.0017 (11)0.0097 (11)0.0080 (11)
C210.0729 (17)0.0762 (16)0.0656 (15)0.0069 (13)0.0146 (13)0.0087 (13)
C220.0811 (18)0.100 (2)0.0695 (16)0.0033 (15)0.0092 (15)0.0010 (15)
C230.096 (2)0.130 (3)0.0749 (19)0.023 (2)0.0071 (18)0.0066 (17)
C240.094 (2)0.136 (3)0.095 (2)0.013 (2)0.0014 (19)0.039 (2)
C250.083 (2)0.099 (2)0.125 (3)0.0096 (16)0.019 (2)0.038 (2)
C260.0870 (19)0.0766 (18)0.0897 (19)0.0032 (15)0.0203 (16)0.0160 (14)
C270.0895 (18)0.0851 (18)0.0739 (16)0.0142 (14)0.0106 (14)0.0070 (14)
C280.0751 (16)0.0727 (16)0.0636 (15)0.0083 (13)0.0044 (12)0.0016 (12)
C290.128 (2)0.0827 (19)0.0781 (19)0.0145 (16)0.0009 (17)0.0078 (16)
C300.161 (3)0.109 (3)0.072 (2)0.040 (2)0.005 (2)0.0102 (18)
C310.123 (3)0.120 (3)0.080 (2)0.049 (2)0.0249 (19)0.025 (2)
C320.0829 (19)0.103 (2)0.095 (2)0.0101 (15)0.0145 (16)0.0314 (18)
C330.0797 (17)0.0833 (18)0.0746 (16)0.0023 (14)0.0089 (13)0.0089 (13)
C340.103 (2)0.0787 (18)0.0713 (16)0.0026 (15)0.0060 (14)0.0103 (13)
C350.0763 (16)0.0734 (16)0.0640 (14)0.0206 (13)0.0179 (12)0.0102 (13)
C360.0646 (16)0.101 (2)0.0794 (16)0.0178 (14)0.0052 (13)0.0093 (15)
C370.0698 (18)0.148 (3)0.0848 (19)0.0010 (18)0.0066 (15)0.0001 (18)
C380.065 (2)0.201 (4)0.098 (2)0.007 (3)0.0026 (17)0.060 (3)
C390.080 (2)0.169 (4)0.149 (4)0.056 (3)0.044 (2)0.083 (3)
C400.106 (2)0.093 (2)0.117 (2)0.0378 (19)0.046 (2)0.0333 (18)
Geometric parameters (Å, º) top
N1—C11.390 (3)N2—C211.380 (3)
N1—C141.445 (3)N2—C341.443 (3)
N1—C71.463 (3)N2—C271.444 (3)
C1—C61.392 (3)C21—C221.392 (3)
C1—C21.401 (3)C21—C261.394 (3)
C2—C31.373 (3)C22—C231.373 (4)
C2—H20.9300C22—H220.9300
C3—C41.371 (3)C23—C241.361 (4)
C3—H30.9300C23—H230.9300
C4—C51.367 (3)C24—C251.371 (4)
C4—H40.9300C24—H240.9300
C5—C61.371 (3)C25—C261.389 (4)
C5—H50.9300C25—H250.9300
C6—H60.9300C26—H260.9300
C7—C81.505 (3)C27—C281.517 (3)
C7—H7A0.9700C27—H27A0.9700
C7—H7B0.9700C27—H27B0.9700
C8—C131.375 (3)C28—C331.369 (3)
C8—C91.379 (3)C28—C291.382 (3)
C9—C101.394 (3)C29—C301.387 (4)
C9—H90.9300C29—H290.9300
C10—C111.366 (4)C30—C311.369 (4)
C10—H100.9300C30—H300.9300
C11—C121.348 (4)C31—C321.357 (4)
C11—H110.9300C31—H310.9300
C12—C131.375 (3)C32—C331.384 (3)
C12—H120.9300C32—H320.9300
C13—H130.9300C33—H330.9300
C14—C151.514 (3)C34—C351.514 (3)
C14—H14A0.9700C34—H34A0.9700
C14—H14B0.9700C34—H34B0.9700
C15—C201.369 (3)C35—C401.370 (3)
C15—C161.377 (3)C35—C361.375 (3)
C16—C171.386 (4)C36—C371.378 (3)
C16—H160.9300C36—H360.9300
C17—C181.356 (4)C37—C381.367 (4)
C17—H170.9300C37—H370.9300
C18—C191.360 (4)C38—C391.357 (5)
C18—H180.9300C38—H380.9300
C19—C201.373 (3)C39—C401.384 (5)
C19—H190.9300C39—H390.9300
C20—H200.9300C40—H400.9300
C1—N1—C14121.58 (18)C21—N2—C34121.8 (2)
C1—N1—C7121.31 (18)C21—N2—C27121.8 (2)
C14—N1—C7113.11 (19)C34—N2—C27116.2 (2)
N1—C1—C6122.0 (2)N2—C21—C22121.1 (2)
N1—C1—C2122.0 (2)N2—C21—C26121.2 (2)
C6—C1—C2116.0 (2)C22—C21—C26117.8 (3)
C3—C2—C1121.1 (2)C23—C22—C21121.3 (3)
C3—C2—H2119.4C23—C22—H22119.4
C1—C2—H2119.4C21—C22—H22119.4
C4—C3—C2121.9 (3)C24—C23—C22120.9 (3)
C4—C3—H3119.1C24—C23—H23119.5
C2—C3—H3119.1C22—C23—H23119.5
C5—C4—C3117.5 (3)C23—C24—C25119.0 (3)
C5—C4—H4121.2C23—C24—H24120.5
C3—C4—H4121.2C25—C24—H24120.5
C4—C5—C6121.7 (3)C24—C25—C26121.3 (3)
C4—C5—H5119.1C24—C25—H25119.3
C6—C5—H5119.1C26—C25—H25119.3
C5—C6—C1121.7 (2)C25—C26—C21119.7 (3)
C5—C6—H6119.2C25—C26—H26120.1
C1—C6—H6119.2C21—C26—H26120.1
N1—C7—C8113.70 (17)N2—C27—C28115.2 (2)
N1—C7—H7A108.8N2—C27—H27A108.5
C8—C7—H7A108.8C28—C27—H27A108.5
N1—C7—H7B108.8N2—C27—H27B108.5
C8—C7—H7B108.8C28—C27—H27B108.5
H7A—C7—H7B107.7H27A—C27—H27B107.5
C13—C8—C9117.7 (2)C33—C28—C29118.7 (2)
C13—C8—C7120.8 (2)C33—C28—C27122.7 (2)
C9—C8—C7121.5 (2)C29—C28—C27118.5 (2)
C8—C9—C10120.5 (2)C28—C29—C30120.0 (3)
C8—C9—H9119.7C28—C29—H29120.0
C10—C9—H9119.7C30—C29—H29120.0
C11—C10—C9120.1 (3)C31—C30—C29120.2 (3)
C11—C10—H10120.0C31—C30—H30119.9
C9—C10—H10120.0C29—C30—H30119.9
C12—C11—C10119.6 (3)C32—C31—C30120.1 (3)
C12—C11—H11120.2C32—C31—H31120.0
C10—C11—H11120.2C30—C31—H31120.0
C11—C12—C13120.7 (3)C31—C32—C33119.9 (3)
C11—C12—H12119.6C31—C32—H32120.0
C13—C12—H12119.6C33—C32—H32120.0
C8—C13—C12121.3 (2)C28—C33—C32121.0 (3)
C8—C13—H13119.3C28—C33—H33119.5
C12—C13—H13119.3C32—C33—H33119.5
N1—C14—C15115.34 (18)N2—C34—C35115.7 (2)
N1—C14—H14A108.4N2—C34—H34A108.4
C15—C14—H14A108.4C35—C34—H34A108.4
N1—C14—H14B108.4N2—C34—H34B108.4
C15—C14—H14B108.4C35—C34—H34B108.4
H14A—C14—H14B107.5H34A—C34—H34B107.4
C20—C15—C16117.5 (2)C40—C35—C36117.5 (3)
C20—C15—C14122.5 (2)C40—C35—C34120.7 (3)
C16—C15—C14120.0 (2)C36—C35—C34121.9 (2)
C15—C16—C17120.7 (3)C35—C36—C37121.7 (3)
C15—C16—H16119.7C35—C36—H36119.1
C17—C16—H16119.7C37—C36—H36119.1
C18—C17—C16120.6 (3)C38—C37—C36119.5 (3)
C18—C17—H17119.7C38—C37—H37120.2
C16—C17—H17119.7C36—C37—H37120.2
C17—C18—C19119.1 (3)C39—C38—C37120.0 (3)
C17—C18—H18120.4C39—C38—H38120.0
C19—C18—H18120.4C37—C38—H38120.0
C18—C19—C20120.4 (3)C38—C39—C40120.0 (3)
C18—C19—H19119.8C38—C39—H39120.0
C20—C19—H19119.8C40—C39—H39120.0
C15—C20—C19121.6 (2)C35—C40—C39121.3 (3)
C15—C20—H20119.2C35—C40—H40119.3
C19—C20—H20119.2C39—C40—H40119.3
 

Subscribe to Acta Crystallographica Section E: Crystallographic Communications

The full text of this article is available to subscribers to the journal.

If you have already registered and are using a computer listed in your registration details, please email support@iucr.org for assistance.

Buy online

You may purchase this article in PDF and/or HTML formats. For purchasers in the European Community who do not have a VAT number, VAT will be added at the local rate. Payments to the IUCr are handled by WorldPay, who will accept payment by credit card in several currencies. To purchase the article, please complete the form below (fields marked * are required), and then click on `Continue'.
E-mail address* 
Repeat e-mail address* 
(for error checking) 

Format*   PDF (US $40)
   HTML (US $40)
   PDF+HTML (US $50)
In order for VAT to be shown for your country javascript needs to be enabled.

VAT number 
(non-UK EC countries only) 
Country* 
 

Terms and conditions of use
Contact us

Follow Acta Cryst. E
Sign up for e-alerts
Follow Acta Cryst. on Twitter
Follow us on facebook
Sign up for RSS feeds