The title compound, C18H28N2, with a crystallographic twofold rotation axis, can function as a C2-symmetric diamine ligand.
Supporting information
CCDC reference: 221696
Key indicators
- Single-crystal X-ray study
- T = 123 K
- Mean (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.
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).
Crystal data top
C18H28N2 | F(000) = 300 |
Mr = 272.42 | Dx = 1.119 Mg m−3 |
Orthorhombic, P22121 | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: P 2bc 2 | Cell parameters from 11552 reflections |
a = 8.5423 (2) Å | θ = 3.8–28.3° |
b = 8.8892 (2) Å | µ = 0.07 mm−1 |
c = 10.6486 (2) Å | T = 123 K |
V = 808.59 (3) Å3 | Prismatic, colourless |
Z = 2 | 0.25 × 0.2 × 0.18 mm |
Data collection top
Nonius KappaCCD diffractometer | Rint = 0.043 |
CCD rotation images, thick slices scans | θmax = 28.3°, θmin = 3.8° |
11552 measured reflections | h = −11→11 |
1174 independent reflections | k = −11→11 |
1094 reflections with I > 2σ(I) | l = −14→14 |
Refinement top
Refinement on F2 | 0 restraints |
Least-squares matrix: full | H-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 = 1.07 | Δρmax = 0.17 e Å−3 |
1174 reflections | Δρmin = −0.16 e Å−3 |
93 parameters | Absolute 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 | x | y | z | Uiso*/Ueq | |
C1 | 0.56474 (15) | 0.44913 (13) | 0.05155 (11) | 0.0217 (3) | |
C2 | 0.42130 (16) | 0.40542 (15) | 0.10227 (13) | 0.0291 (3) | |
H2 | 0.4202 | 0.3407 | 0.1733 | 0.035* | |
C3 | 0.28012 (17) | 0.45362 (16) | 0.05207 (14) | 0.0338 (3) | |
H3 | 0.1840 | 0.4231 | 0.0890 | 0.041* | |
C4 | 0.71578 (17) | 0.33212 (16) | 0.22648 (13) | 0.0314 (3) | |
H4 | 0.6418 | 0.2453 | 0.2331 | 0.038* | |
C5 | 0.88399 (18) | 0.27523 (19) | 0.23052 (16) | 0.0388 (4) | |
H5A | 0.9584 | 0.3588 | 0.2451 | 0.047* | |
H5B | 0.8978 | 0.1986 | 0.2971 | 0.047* | |
C6 | 0.90611 (18) | 0.20718 (16) | 0.10109 (16) | 0.0364 (4) | |
H6A | 0.8656 | 0.1029 | 0.0986 | 0.044* | |
H6B | 1.0182 | 0.2063 | 0.0775 | 0.044* | |
C7 | 0.81213 (14) | 0.30934 (14) | 0.01259 (13) | 0.0257 (3) | |
H7 | 0.8853 | 0.3803 | −0.0306 | 0.031* | |
C8 | 0.6788 (2) | 0.4468 (2) | 0.32756 (13) | 0.0441 (4) | |
H8A | 0.7543 | 0.5296 | 0.3230 | 0.066* | |
H8B | 0.6855 | 0.3988 | 0.4102 | 0.066* | |
H8C | 0.5728 | 0.4860 | 0.3148 | 0.066* | |
C9 | 0.72306 (18) | 0.21970 (16) | −0.08556 (15) | 0.0345 (3) | |
H9A | 0.6495 | 0.1515 | −0.0438 | 0.052* | |
H9B | 0.7971 | 0.1611 | −0.1360 | 0.052* | |
H9C | 0.6651 | 0.2887 | −0.1402 | 0.052* | |
N1 | 0.70859 (13) | 0.39613 (11) | 0.09903 (10) | 0.0227 (3) | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
C1 | 0.0227 (6) | 0.0206 (5) | 0.0219 (5) | −0.0018 (5) | −0.0009 (5) | −0.0023 (5) |
C2 | 0.0289 (7) | 0.0290 (6) | 0.0293 (6) | −0.0064 (5) | 0.0037 (6) | −0.0004 (6) |
C3 | 0.0228 (6) | 0.0363 (7) | 0.0423 (7) | −0.0040 (6) | 0.0046 (6) | −0.0069 (7) |
C4 | 0.0337 (7) | 0.0354 (7) | 0.0252 (6) | −0.0106 (6) | −0.0062 (6) | 0.0117 (6) |
C5 | 0.0365 (8) | 0.0394 (8) | 0.0406 (8) | −0.0075 (7) | −0.0142 (7) | 0.0168 (7) |
C6 | 0.0317 (7) | 0.0256 (6) | 0.0518 (9) | 0.0001 (6) | −0.0118 (7) | 0.0089 (7) |
C7 | 0.0243 (6) | 0.0200 (5) | 0.0327 (7) | 0.0008 (5) | −0.0022 (6) | 0.0012 (5) |
C8 | 0.0501 (10) | 0.0596 (10) | 0.0225 (6) | −0.0139 (9) | −0.0016 (7) | 0.0018 (8) |
C9 | 0.0367 (8) | 0.0278 (6) | 0.0389 (8) | 0.0070 (6) | −0.0071 (7) | −0.0094 (7) |
N1 | 0.0239 (5) | 0.0240 (5) | 0.0202 (5) | −0.0014 (4) | −0.0011 (4) | 0.0033 (5) |
Geometric parameters (Å, º) top
C1—C2 | 1.3943 (18) | C5—H5B | 0.9900 |
C1—N1 | 1.4098 (16) | C6—C7 | 1.5354 (19) |
C1—C1i | 1.422 (2) | C6—H6A | 0.9900 |
C2—C3 | 1.387 (2) | C6—H6B | 0.9900 |
C2—H2 | 0.9500 | C7—N1 | 1.4915 (17) |
C3—C3i | 1.382 (3) | C7—C9 | 1.5186 (19) |
C3—H3 | 0.9500 | C7—H7 | 1.0000 |
C4—N1 | 1.4729 (16) | C8—H8A | 0.9800 |
C4—C8 | 1.515 (2) | C8—H8B | 0.9800 |
C4—C5 | 1.524 (2) | C8—H8C | 0.9800 |
C4—H4 | 1.0000 | C9—H9A | 0.9800 |
C5—C6 | 1.517 (2) | C9—H9B | 0.9800 |
C5—H5A | 0.9900 | C9—H9C | 0.9800 |
| | | |
C2—C1—N1 | 122.27 (11) | C5—C6—H6B | 110.8 |
C2—C1—C1i | 118.43 (8) | C7—C6—H6B | 110.8 |
N1—C1—C1i | 119.29 (6) | H6A—C6—H6B | 108.8 |
C3—C2—C1 | 121.92 (12) | N1—C7—C9 | 113.52 (10) |
C3—C2—H2 | 119.0 | N1—C7—C6 | 103.72 (11) |
C1—C2—H2 | 119.0 | C9—C7—C6 | 111.97 (11) |
C3i—C3—C2 | 119.58 (8) | N1—C7—H7 | 109.2 |
C3i—C3—H3 | 120.2 | C9—C7—H7 | 109.2 |
C2—C3—H3 | 120.2 | C6—C7—H7 | 109.2 |
N1—C4—C8 | 112.70 (12) | C4—C8—H8A | 109.5 |
N1—C4—C5 | 101.16 (12) | C4—C8—H8B | 109.5 |
C8—C4—C5 | 113.54 (13) | H8A—C8—H8B | 109.5 |
N1—C4—H4 | 109.7 | C4—C8—H8C | 109.5 |
C8—C4—H4 | 109.7 | H8A—C8—H8C | 109.5 |
C5—C4—H4 | 109.7 | H8B—C8—H8C | 109.5 |
C6—C5—C4 | 102.95 (12) | C7—C9—H9A | 109.5 |
C6—C5—H5A | 111.2 | C7—C9—H9B | 109.5 |
C4—C5—H5A | 111.2 | H9A—C9—H9B | 109.5 |
C6—C5—H5B | 111.2 | C7—C9—H9C | 109.5 |
C4—C5—H5B | 111.2 | H9A—C9—H9C | 109.5 |
H5A—C5—H5B | 109.1 | H9B—C9—H9C | 109.5 |
C5—C6—C7 | 104.87 (12) | C1—N1—C4 | 119.73 (11) |
C5—C6—H6A | 110.8 | C1—N1—C7 | 117.93 (10) |
C7—C6—H6A | 110.8 | C4—N1—C7 | 110.13 (10) |
Symmetry code: (i) x, −y+1, −z. |