Download citation
Download citation
link to html
The title compound, C18H28N2, with a crystallographic twofold rotation axis, can function as a C2-symmetric di­amine ligand.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S160053680301537X/tk6121sup1.cif
Contains datablocks global, I

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S160053680301537X/tk6121Isup2.hkl
Contains datablock I

CCDC reference: 221696

Key indicators

  • Single-crystal X-ray study
  • T = 123 K
  • Mean [sigma](C-C) = 0.002 Å
  • R factor = 0.033
  • wR factor = 0.084
  • Data-to-parameter ratio = 12.6

checkCIF results

No syntax errors found

ADDSYM reports no extra symmetry

General Notes

REFLT_03 From the CIF: _diffrn_reflns_theta_max 28.30 From the CIF: _reflns_number_total 1174 Count of symmetry unique reflns 1185 Completeness (_total/calc) 99.07% 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 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.

Computing details top

Data collection: COLLECT (Nonius, 1997-2000); cell refinement: HKL SCALEPACK (Otwinowski & Minor, 1997); data reduction: HKL DENZO (Otwinowski & Minor, 1997) and SCALEPACK; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997); software used to prepare material for publication: WinGX publication routines (Farrugia, 1999).

(I) top
Crystal data top
C18H28N2F(000) = 300
Mr = 272.42Dx = 1.119 Mg m3
Orthorhombic, P22121Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2bc 2Cell parameters from 11552 reflections
a = 8.5423 (2) Åθ = 3.8–28.3°
b = 8.8892 (2) ŵ = 0.07 mm1
c = 10.6486 (2) ÅT = 123 K
V = 808.59 (3) Å3Prismatic, colourless
Z = 20.25 × 0.2 × 0.18 mm
Data collection top
Nonius KappaCCD
diffractometer
Rint = 0.043
CCD rotation images, thick slices scansθmax = 28.3°, θmin = 3.8°
11552 measured reflectionsh = 1111
1174 independent reflectionsk = 1111
1094 reflections with I > 2σ(I)l = 1414
Refinement top
Refinement on F20 restraints
Least-squares matrix: fullH-atom parameters constrained
R[F2 > 2σ(F2)] = 0.033 w = 1/[σ2(Fo2) + (0.0398P)2 + 0.1166P]
where P = (Fo2 + 2Fc2)/3
wR(F2) = 0.084(Δ/σ)max < 0.001
S = 1.07Δρmax = 0.17 e Å3
1174 reflectionsΔρmin = 0.16 e Å3
93 parametersAbsolute structure: Friedel opposites merged
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.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
C10.56474 (15)0.44913 (13)0.05155 (11)0.0217 (3)
C20.42130 (16)0.40542 (15)0.10227 (13)0.0291 (3)
H20.42020.34070.17330.035*
C30.28012 (17)0.45362 (16)0.05207 (14)0.0338 (3)
H30.18400.42310.08900.041*
C40.71578 (17)0.33212 (16)0.22648 (13)0.0314 (3)
H40.64180.24530.23310.038*
C50.88399 (18)0.27523 (19)0.23052 (16)0.0388 (4)
H5A0.95840.35880.24510.047*
H5B0.89780.19860.29710.047*
C60.90611 (18)0.20718 (16)0.10109 (16)0.0364 (4)
H6A0.86560.10290.09860.044*
H6B1.01820.20630.07750.044*
C70.81213 (14)0.30934 (14)0.01259 (13)0.0257 (3)
H70.88530.38030.03060.031*
C80.6788 (2)0.4468 (2)0.32756 (13)0.0441 (4)
H8A0.75430.52960.32300.066*
H8B0.68550.39880.41020.066*
H8C0.57280.48600.31480.066*
C90.72306 (18)0.21970 (16)0.08556 (15)0.0345 (3)
H9A0.64950.15150.04380.052*
H9B0.79710.16110.13600.052*
H9C0.66510.28870.14020.052*
N10.70859 (13)0.39613 (11)0.09903 (10)0.0227 (3)
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
C10.0227 (6)0.0206 (5)0.0219 (5)0.0018 (5)0.0009 (5)0.0023 (5)
C20.0289 (7)0.0290 (6)0.0293 (6)0.0064 (5)0.0037 (6)0.0004 (6)
C30.0228 (6)0.0363 (7)0.0423 (7)0.0040 (6)0.0046 (6)0.0069 (7)
C40.0337 (7)0.0354 (7)0.0252 (6)0.0106 (6)0.0062 (6)0.0117 (6)
C50.0365 (8)0.0394 (8)0.0406 (8)0.0075 (7)0.0142 (7)0.0168 (7)
C60.0317 (7)0.0256 (6)0.0518 (9)0.0001 (6)0.0118 (7)0.0089 (7)
C70.0243 (6)0.0200 (5)0.0327 (7)0.0008 (5)0.0022 (6)0.0012 (5)
C80.0501 (10)0.0596 (10)0.0225 (6)0.0139 (9)0.0016 (7)0.0018 (8)
C90.0367 (8)0.0278 (6)0.0389 (8)0.0070 (6)0.0071 (7)0.0094 (7)
N10.0239 (5)0.0240 (5)0.0202 (5)0.0014 (4)0.0011 (4)0.0033 (5)
Geometric parameters (Å, º) top
C1—C21.3943 (18)C5—H5B0.9900
C1—N11.4098 (16)C6—C71.5354 (19)
C1—C1i1.422 (2)C6—H6A0.9900
C2—C31.387 (2)C6—H6B0.9900
C2—H20.9500C7—N11.4915 (17)
C3—C3i1.382 (3)C7—C91.5186 (19)
C3—H30.9500C7—H71.0000
C4—N11.4729 (16)C8—H8A0.9800
C4—C81.515 (2)C8—H8B0.9800
C4—C51.524 (2)C8—H8C0.9800
C4—H41.0000C9—H9A0.9800
C5—C61.517 (2)C9—H9B0.9800
C5—H5A0.9900C9—H9C0.9800
C2—C1—N1122.27 (11)C5—C6—H6B110.8
C2—C1—C1i118.43 (8)C7—C6—H6B110.8
N1—C1—C1i119.29 (6)H6A—C6—H6B108.8
C3—C2—C1121.92 (12)N1—C7—C9113.52 (10)
C3—C2—H2119.0N1—C7—C6103.72 (11)
C1—C2—H2119.0C9—C7—C6111.97 (11)
C3i—C3—C2119.58 (8)N1—C7—H7109.2
C3i—C3—H3120.2C9—C7—H7109.2
C2—C3—H3120.2C6—C7—H7109.2
N1—C4—C8112.70 (12)C4—C8—H8A109.5
N1—C4—C5101.16 (12)C4—C8—H8B109.5
C8—C4—C5113.54 (13)H8A—C8—H8B109.5
N1—C4—H4109.7C4—C8—H8C109.5
C8—C4—H4109.7H8A—C8—H8C109.5
C5—C4—H4109.7H8B—C8—H8C109.5
C6—C5—C4102.95 (12)C7—C9—H9A109.5
C6—C5—H5A111.2C7—C9—H9B109.5
C4—C5—H5A111.2H9A—C9—H9B109.5
C6—C5—H5B111.2C7—C9—H9C109.5
C4—C5—H5B111.2H9A—C9—H9C109.5
H5A—C5—H5B109.1H9B—C9—H9C109.5
C5—C6—C7104.87 (12)C1—N1—C4119.73 (11)
C5—C6—H6A110.8C1—N1—C7117.93 (10)
C7—C6—H6A110.8C4—N1—C7110.13 (10)
Symmetry code: (i) x, y+1, z.
 

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