Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536807036859/wn2159sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S1600536807036859/wn2159Isup2.hkl |
CCDC reference: 649510
To a solution of benzaldehyde (20 mmol) in methanol (20 ml) propane-1,3-diamine (10 mmol) in methanol (10 ml) was added. The mixed solution was stirred for 10 min and then acetic acid catalyst was added. The reaction mixture was stirred continuously for 10 h at 338 K and then filtered. The solution was allowed to stand, slowly producing crystals of the title compound.
All H atoms were located in difference Fourier maps. They were then treated as riding, with C—H distances of 0.93 Å (aryl), 0.97 Å (methylene) and 0.98 Å (methine); Uiso(H) = 1.2Ueq(C).
As part of our investigation of crystal structures of diamine derivatives, we report here the crystal structure of a new diamine derivative.
The molecular structure of the title compound is illustrated in Fig. 1. The bond lengths and angles are normal (Allen et al., 1987). A very closely related compound is 1,3-dibenzyl-2-phenylimidazolidine (Xia et al., 2007); it and the title compound have similar crystal structures. In the title compound, the dihedral angles between the central phenyl ring (C5—C10) and the other two phenyl rings are 78.53 (10)° (C12—C1) and 79.37 (10)° (C19—C24) (Fig. 1). Molecules are linked into chains of rings and a three-dimensional network by C—H···π hydrogen bonds (Fig. 2 and Fig. 3).
For bond- length data, see: Allen et al. (1987). For a related structure, see: Xia et al. (2007).
Data collection: SMART (Siemens, 1996); cell refinement: SMART; data reduction: SAINT (Siemens, 1996); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997a); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997a); molecular graphics: SHELXTL (Sheldrick, 1997b); software used to prepare material for publication: SHELXTL.
C24H26N2 | F(000) = 736 |
Mr = 342.47 | Dx = 1.138 Mg m−3 |
Monoclinic, P21/n | Mo Kα radiation, λ = 0.71073 Å |
a = 6.0912 (11) Å | Cell parameters from 926 reflections |
b = 16.900 (2) Å | θ = 2.4–18.6° |
c = 19.621 (3) Å | µ = 0.07 mm−1 |
β = 98.304 (2)° | T = 298 K |
V = 1998.7 (5) Å3 | Block, colorless |
Z = 4 | 0.35 × 0.17 × 0.15 mm |
Bruker SMART CCD area-detector diffractometer | 3522 independent reflections |
Radiation source: fine-focus sealed tube | 1341 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.073 |
φ and ω scans | θmax = 25.0°, θmin = 1.6° |
Absorption correction: multi-scan (SADABS; Sheldrick, 1996) | h = −7→6 |
Tmin = 0.977, Tmax = 0.990 | k = −20→17 |
9972 measured reflections | l = −23→23 |
Refinement on F2 | Primary atom site location: structure-invariant direct methods |
Least-squares matrix: full | Secondary atom site location: difference Fourier map |
R[F2 > 2σ(F2)] = 0.045 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.094 | H-atom parameters constrained |
S = 0.75 | w = 1/[σ2(Fo2) + (0.0279P)2] where P = (Fo2 + 2Fc2)/3 |
3522 reflections | (Δ/σ)max < 0.001 |
235 parameters | Δρmax = 0.13 e Å−3 |
0 restraints | Δρmin = −0.14 e Å−3 |
C24H26N2 | V = 1998.7 (5) Å3 |
Mr = 342.47 | Z = 4 |
Monoclinic, P21/n | Mo Kα radiation |
a = 6.0912 (11) Å | µ = 0.07 mm−1 |
b = 16.900 (2) Å | T = 298 K |
c = 19.621 (3) Å | 0.35 × 0.17 × 0.15 mm |
β = 98.304 (2)° |
Bruker SMART CCD area-detector diffractometer | 3522 independent reflections |
Absorption correction: multi-scan (SADABS; Sheldrick, 1996) | 1341 reflections with I > 2σ(I) |
Tmin = 0.977, Tmax = 0.990 | Rint = 0.073 |
9972 measured reflections |
R[F2 > 2σ(F2)] = 0.045 | 0 restraints |
wR(F2) = 0.094 | H-atom parameters constrained |
S = 0.75 | Δρmax = 0.13 e Å−3 |
3522 reflections | Δρmin = −0.14 e Å−3 |
235 parameters |
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. |
x | y | z | Uiso*/Ueq | ||
N1 | 0.7318 (3) | 0.85935 (10) | 0.06611 (9) | 0.0516 (5) | |
N2 | 0.7249 (3) | 0.88698 (10) | 0.18657 (9) | 0.0521 (6) | |
C1 | 0.8029 (4) | 0.94061 (13) | 0.05542 (11) | 0.0692 (8) | |
H1A | 0.6737 | 0.9739 | 0.0427 | 0.083* | |
H1B | 0.8911 | 0.9418 | 0.0181 | 0.083* | |
C2 | 0.9374 (5) | 0.97215 (13) | 0.11995 (12) | 0.0740 (9) | |
H2A | 1.0714 | 0.9410 | 0.1314 | 0.089* | |
H2B | 0.9799 | 1.0265 | 0.1129 | 0.089* | |
C3 | 0.8003 (4) | 0.96792 (13) | 0.17753 (12) | 0.0671 (8) | |
H3A | 0.8878 | 0.9860 | 0.2199 | 0.080* | |
H3B | 0.6728 | 1.0026 | 0.1674 | 0.080* | |
C4 | 0.5999 (4) | 0.85434 (12) | 0.12315 (11) | 0.0517 (7) | |
H4 | 0.4616 | 0.8841 | 0.1112 | 0.062* | |
C5 | 0.5463 (5) | 0.76804 (13) | 0.13427 (11) | 0.0473 (6) | |
C6 | 0.7146 (4) | 0.71554 (14) | 0.15560 (11) | 0.0591 (7) | |
H6 | 0.8593 | 0.7341 | 0.1661 | 0.071* | |
C7 | 0.6732 (5) | 0.63590 (15) | 0.16175 (12) | 0.0708 (8) | |
H7 | 0.7893 | 0.6012 | 0.1759 | 0.085* | |
C8 | 0.4605 (6) | 0.60803 (16) | 0.14691 (13) | 0.0718 (9) | |
H8 | 0.4320 | 0.5543 | 0.1506 | 0.086* | |
C9 | 0.2902 (5) | 0.65937 (17) | 0.12665 (12) | 0.0683 (8) | |
H9 | 0.1459 | 0.6404 | 0.1164 | 0.082* | |
C10 | 0.3317 (5) | 0.73931 (15) | 0.12132 (10) | 0.0583 (7) | |
H10 | 0.2144 | 0.7741 | 0.1089 | 0.070* | |
C11 | 0.6008 (4) | 0.83060 (13) | 0.00211 (11) | 0.0606 (8) | |
H11A | 0.4752 | 0.8657 | −0.0100 | 0.073* | |
H11B | 0.5428 | 0.7786 | 0.0106 | 0.073* | |
C12 | 0.7262 (5) | 0.82518 (13) | −0.05768 (12) | 0.0519 (7) | |
C13 | 0.9340 (5) | 0.79109 (14) | −0.05116 (13) | 0.0653 (8) | |
H13 | 1.0002 | 0.7736 | −0.0081 | 0.078* | |
C14 | 1.0453 (5) | 0.78237 (14) | −0.10665 (17) | 0.0744 (9) | |
H14 | 1.1846 | 0.7588 | −0.1011 | 0.089* | |
C15 | 0.9499 (6) | 0.80870 (16) | −0.17072 (16) | 0.0817 (10) | |
H15 | 1.0253 | 0.8038 | −0.2085 | 0.098* | |
C16 | 0.7445 (6) | 0.84185 (16) | −0.17795 (14) | 0.0802 (10) | |
H16 | 0.6784 | 0.8590 | −0.2211 | 0.096* | |
C17 | 0.6333 (5) | 0.85023 (13) | −0.12196 (13) | 0.0648 (8) | |
H17 | 0.4931 | 0.8732 | −0.1278 | 0.078* | |
C18 | 0.5896 (4) | 0.88619 (13) | 0.24232 (11) | 0.0629 (8) | |
H18A | 0.5094 | 0.8365 | 0.2408 | 0.075* | |
H18B | 0.4810 | 0.9284 | 0.2345 | 0.075* | |
C19 | 0.7200 (5) | 0.89608 (13) | 0.31294 (12) | 0.0546 (7) | |
C20 | 0.9327 (5) | 0.86625 (13) | 0.32864 (14) | 0.0680 (8) | |
H20 | 1.0010 | 0.8428 | 0.2943 | 0.082* | |
C21 | 1.0450 (5) | 0.87117 (16) | 0.39527 (18) | 0.0851 (10) | |
H21 | 1.1887 | 0.8516 | 0.4054 | 0.102* | |
C22 | 0.9438 (7) | 0.9048 (2) | 0.44608 (17) | 0.0984 (13) | |
H22 | 1.0182 | 0.9071 | 0.4909 | 0.118* | |
C23 | 0.7348 (7) | 0.93502 (17) | 0.43139 (16) | 0.0968 (11) | |
H23 | 0.6671 | 0.9583 | 0.4660 | 0.116* | |
C24 | 0.6234 (5) | 0.93087 (14) | 0.36457 (14) | 0.0732 (9) | |
H24 | 0.4814 | 0.9519 | 0.3546 | 0.088* |
U11 | U22 | U33 | U12 | U13 | U23 | |
N1 | 0.0641 (16) | 0.0516 (12) | 0.0404 (12) | −0.0082 (11) | 0.0117 (11) | −0.0015 (9) |
N2 | 0.0646 (16) | 0.0502 (13) | 0.0428 (12) | −0.0040 (11) | 0.0117 (12) | −0.0028 (9) |
C1 | 0.093 (2) | 0.0613 (17) | 0.0557 (17) | −0.0117 (16) | 0.0182 (16) | 0.0004 (13) |
C2 | 0.104 (3) | 0.0551 (17) | 0.0645 (18) | −0.0254 (16) | 0.0181 (18) | −0.0069 (13) |
C3 | 0.090 (2) | 0.0521 (17) | 0.0596 (18) | −0.0055 (15) | 0.0115 (17) | −0.0064 (13) |
C4 | 0.056 (2) | 0.0507 (15) | 0.0484 (16) | 0.0031 (13) | 0.0064 (14) | 0.0011 (12) |
C5 | 0.0499 (19) | 0.0489 (16) | 0.0443 (15) | −0.0022 (15) | 0.0106 (13) | −0.0009 (11) |
C6 | 0.056 (2) | 0.0550 (18) | 0.0674 (18) | −0.0019 (16) | 0.0131 (15) | 0.0020 (13) |
C7 | 0.073 (3) | 0.0581 (19) | 0.083 (2) | 0.0035 (17) | 0.0167 (17) | 0.0032 (15) |
C8 | 0.099 (3) | 0.0528 (18) | 0.0680 (19) | −0.010 (2) | 0.0271 (18) | −0.0052 (14) |
C9 | 0.069 (2) | 0.075 (2) | 0.0628 (19) | −0.0212 (18) | 0.0157 (16) | −0.0071 (15) |
C10 | 0.058 (2) | 0.0631 (19) | 0.0537 (16) | 0.0000 (16) | 0.0094 (14) | 0.0011 (13) |
C11 | 0.066 (2) | 0.0688 (17) | 0.0466 (16) | −0.0071 (14) | 0.0057 (15) | −0.0015 (13) |
C12 | 0.059 (2) | 0.0531 (15) | 0.0438 (17) | −0.0041 (14) | 0.0073 (15) | −0.0037 (12) |
C13 | 0.073 (3) | 0.0735 (19) | 0.0478 (18) | −0.0067 (17) | 0.0042 (17) | −0.0040 (13) |
C14 | 0.072 (2) | 0.0720 (19) | 0.080 (2) | −0.0004 (16) | 0.014 (2) | −0.0170 (17) |
C15 | 0.106 (3) | 0.081 (2) | 0.065 (2) | −0.024 (2) | 0.035 (2) | −0.0200 (17) |
C16 | 0.103 (3) | 0.090 (2) | 0.0460 (19) | −0.008 (2) | 0.007 (2) | 0.0081 (15) |
C17 | 0.077 (2) | 0.0652 (18) | 0.0518 (18) | −0.0026 (15) | 0.0084 (17) | 0.0077 (14) |
C18 | 0.072 (2) | 0.0606 (16) | 0.0574 (18) | 0.0007 (14) | 0.0125 (16) | −0.0042 (13) |
C19 | 0.071 (2) | 0.0518 (15) | 0.0434 (17) | −0.0032 (15) | 0.0146 (16) | −0.0002 (13) |
C20 | 0.080 (3) | 0.0595 (17) | 0.065 (2) | 0.0001 (17) | 0.0114 (17) | 0.0063 (14) |
C21 | 0.090 (3) | 0.076 (2) | 0.083 (2) | −0.0110 (18) | −0.009 (2) | 0.0248 (18) |
C22 | 0.131 (4) | 0.101 (3) | 0.060 (2) | −0.036 (3) | 0.003 (3) | 0.0060 (19) |
C23 | 0.128 (4) | 0.102 (3) | 0.065 (3) | −0.021 (2) | 0.033 (2) | −0.0185 (19) |
C24 | 0.089 (3) | 0.0736 (19) | 0.0603 (19) | −0.0089 (16) | 0.0198 (18) | −0.0079 (15) |
N1—C1 | 1.464 (2) | C11—H11A | 0.9700 |
N1—C11 | 1.470 (2) | C11—H11B | 0.9700 |
N1—C4 | 1.472 (3) | C12—C17 | 1.373 (3) |
N2—C18 | 1.462 (3) | C12—C13 | 1.380 (3) |
N2—C3 | 1.462 (2) | C13—C14 | 1.371 (3) |
N2—C4 | 1.469 (2) | C13—H13 | 0.9300 |
C1—C2 | 1.503 (3) | C14—C15 | 1.380 (3) |
C1—H1A | 0.9700 | C14—H14 | 0.9300 |
C1—H1B | 0.9700 | C15—C16 | 1.359 (4) |
C2—C3 | 1.501 (3) | C15—H15 | 0.9300 |
C2—H2A | 0.9700 | C16—C17 | 1.379 (4) |
C2—H2B | 0.9700 | C16—H16 | 0.9300 |
C3—H3A | 0.9700 | C17—H17 | 0.9300 |
C3—H3B | 0.9700 | C18—C19 | 1.504 (3) |
C4—C5 | 1.517 (3) | C18—H18A | 0.9700 |
C4—H4 | 0.9800 | C18—H18B | 0.9700 |
C5—C6 | 1.375 (3) | C19—C24 | 1.375 (3) |
C5—C10 | 1.383 (3) | C19—C20 | 1.383 (3) |
C6—C7 | 1.378 (3) | C20—C21 | 1.388 (3) |
C6—H6 | 0.9300 | C20—H20 | 0.9300 |
C7—C8 | 1.370 (3) | C21—C22 | 1.369 (4) |
C7—H7 | 0.9300 | C21—H21 | 0.9300 |
C8—C9 | 1.366 (3) | C22—C23 | 1.364 (4) |
C8—H8 | 0.9300 | C22—H22 | 0.9300 |
C9—C10 | 1.381 (3) | C23—C24 | 1.388 (3) |
C9—H9 | 0.9300 | C23—H23 | 0.9300 |
C10—H10 | 0.9300 | C24—H24 | 0.9300 |
C11—C12 | 1.492 (3) | ||
C1—N1—C11 | 108.85 (17) | N1—C11—C12 | 114.5 (2) |
C1—N1—C4 | 111.60 (18) | N1—C11—H11A | 108.6 |
C11—N1—C4 | 110.00 (19) | C12—C11—H11A | 108.6 |
C18—N2—C3 | 108.68 (18) | N1—C11—H11B | 108.6 |
C18—N2—C4 | 110.6 (2) | C12—C11—H11B | 108.6 |
C3—N2—C4 | 112.45 (17) | H11A—C11—H11B | 107.6 |
N1—C1—C2 | 110.40 (18) | C17—C12—C13 | 117.7 (3) |
N1—C1—H1A | 109.6 | C17—C12—C11 | 120.9 (3) |
C2—C1—H1A | 109.6 | C13—C12—C11 | 121.3 (2) |
N1—C1—H1B | 109.6 | C14—C13—C12 | 121.6 (3) |
C2—C1—H1B | 109.6 | C14—C13—H13 | 119.2 |
H1A—C1—H1B | 108.1 | C12—C13—H13 | 119.2 |
C3—C2—C1 | 108.8 (2) | C13—C14—C15 | 119.8 (3) |
C3—C2—H2A | 109.9 | C13—C14—H14 | 120.1 |
C1—C2—H2A | 109.9 | C15—C14—H14 | 120.1 |
C3—C2—H2B | 109.9 | C16—C15—C14 | 119.2 (3) |
C1—C2—H2B | 109.9 | C16—C15—H15 | 120.4 |
H2A—C2—H2B | 108.3 | C14—C15—H15 | 120.4 |
N2—C3—C2 | 110.77 (19) | C15—C16—C17 | 120.7 (3) |
N2—C3—H3A | 109.5 | C15—C16—H16 | 119.7 |
C2—C3—H3A | 109.5 | C17—C16—H16 | 119.7 |
N2—C3—H3B | 109.5 | C12—C17—C16 | 121.0 (3) |
C2—C3—H3B | 109.5 | C12—C17—H17 | 119.5 |
H3A—C3—H3B | 108.1 | C16—C17—H17 | 119.5 |
N2—C4—N1 | 110.4 (2) | N2—C18—C19 | 114.1 (2) |
N2—C4—C5 | 109.58 (17) | N2—C18—H18A | 108.7 |
N1—C4—C5 | 108.50 (18) | C19—C18—H18A | 108.7 |
N2—C4—H4 | 109.4 | N2—C18—H18B | 108.7 |
N1—C4—H4 | 109.4 | C19—C18—H18B | 108.7 |
C5—C4—H4 | 109.4 | H18A—C18—H18B | 107.6 |
C6—C5—C10 | 118.2 (2) | C24—C19—C20 | 118.6 (3) |
C6—C5—C4 | 119.8 (2) | C24—C19—C18 | 120.1 (3) |
C10—C5—C4 | 121.9 (2) | C20—C19—C18 | 121.2 (2) |
C5—C6—C7 | 121.3 (2) | C19—C20—C21 | 120.4 (3) |
C5—C6—H6 | 119.4 | C19—C20—H20 | 119.8 |
C7—C6—H6 | 119.4 | C21—C20—H20 | 119.8 |
C8—C7—C6 | 119.8 (3) | C22—C21—C20 | 119.9 (3) |
C8—C7—H7 | 120.1 | C22—C21—H21 | 120.0 |
C6—C7—H7 | 120.1 | C20—C21—H21 | 120.0 |
C9—C8—C7 | 119.9 (3) | C23—C22—C21 | 120.4 (3) |
C9—C8—H8 | 120.1 | C23—C22—H22 | 119.8 |
C7—C8—H8 | 120.1 | C21—C22—H22 | 119.8 |
C8—C9—C10 | 120.3 (3) | C22—C23—C24 | 119.7 (3) |
C8—C9—H9 | 119.9 | C22—C23—H23 | 120.2 |
C10—C9—H9 | 119.9 | C24—C23—H23 | 120.2 |
C9—C10—C5 | 120.5 (2) | C19—C24—C23 | 121.0 (3) |
C9—C10—H10 | 119.7 | C19—C24—H24 | 119.5 |
C5—C10—H10 | 119.7 | C23—C24—H24 | 119.5 |
C11—N1—C1—C2 | 179.9 (2) | C4—C5—C10—C9 | 174.78 (19) |
C4—N1—C1—C2 | 58.3 (3) | C1—N1—C11—C12 | 63.4 (3) |
N1—C1—C2—C3 | −57.8 (3) | C4—N1—C11—C12 | −173.99 (19) |
C18—N2—C3—C2 | −179.1 (2) | N1—C11—C12—C17 | −137.0 (2) |
C4—N2—C3—C2 | −56.4 (3) | N1—C11—C12—C13 | 46.5 (3) |
C1—C2—C3—N2 | 56.7 (3) | C17—C12—C13—C14 | 0.1 (4) |
C18—N2—C4—N1 | 176.79 (17) | C11—C12—C13—C14 | 176.7 (2) |
C3—N2—C4—N1 | 55.1 (2) | C12—C13—C14—C15 | 0.6 (4) |
C18—N2—C4—C5 | −63.7 (2) | C13—C14—C15—C16 | −1.1 (4) |
C3—N2—C4—C5 | 174.6 (2) | C14—C15—C16—C17 | 0.9 (4) |
C1—N1—C4—N2 | −56.0 (2) | C13—C12—C17—C16 | −0.3 (3) |
C11—N1—C4—N2 | −176.92 (16) | C11—C12—C17—C16 | −176.9 (2) |
C1—N1—C4—C5 | −176.11 (18) | C15—C16—C17—C12 | −0.2 (4) |
C11—N1—C4—C5 | 63.0 (2) | C3—N2—C18—C19 | −72.8 (2) |
N2—C4—C5—C6 | −56.2 (3) | C4—N2—C18—C19 | 163.38 (17) |
N1—C4—C5—C6 | 64.5 (3) | N2—C18—C19—C24 | 150.9 (2) |
N2—C4—C5—C10 | 126.1 (2) | N2—C18—C19—C20 | −33.2 (3) |
N1—C4—C5—C10 | −113.3 (2) | C24—C19—C20—C21 | 0.3 (4) |
C10—C5—C6—C7 | 2.2 (3) | C18—C19—C20—C21 | −175.6 (2) |
C4—C5—C6—C7 | −175.6 (2) | C19—C20—C21—C22 | 0.8 (4) |
C5—C6—C7—C8 | −0.5 (4) | C20—C21—C22—C23 | −1.3 (5) |
C6—C7—C8—C9 | −0.6 (4) | C21—C22—C23—C24 | 0.6 (5) |
C7—C8—C9—C10 | −0.3 (4) | C20—C19—C24—C23 | −1.0 (4) |
C8—C9—C10—C5 | 2.1 (4) | C18—C19—C24—C23 | 174.9 (2) |
C6—C5—C10—C9 | −3.0 (3) | C22—C23—C24—C19 | 0.6 (4) |
D—H···A | D—H | H···A | D···A | D—H···A |
C14—H14···Cg1i | 0.93 | 2.85 | 3.55 (3) | 132 |
C8—H8···Cg1ii | 0.93 | 3.07 | 3.79 (3) | 136 |
C21—H21···Cg2iii | 0.93 | 3.00 | 3.63 (4) | 126 |
Symmetry codes: (i) x+1/2, −y+3/2, z−1/2; (ii) −x+3/2, y−1/2, −z+1/2; (iii) x+1/2, −y+3/2, z+1/2. |
Experimental details
Crystal data | |
Chemical formula | C24H26N2 |
Mr | 342.47 |
Crystal system, space group | Monoclinic, P21/n |
Temperature (K) | 298 |
a, b, c (Å) | 6.0912 (11), 16.900 (2), 19.621 (3) |
β (°) | 98.304 (2) |
V (Å3) | 1998.7 (5) |
Z | 4 |
Radiation type | Mo Kα |
µ (mm−1) | 0.07 |
Crystal size (mm) | 0.35 × 0.17 × 0.15 |
Data collection | |
Diffractometer | Bruker SMART CCD area-detector |
Absorption correction | Multi-scan (SADABS; Sheldrick, 1996) |
Tmin, Tmax | 0.977, 0.990 |
No. of measured, independent and observed [I > 2σ(I)] reflections | 9972, 3522, 1341 |
Rint | 0.073 |
(sin θ/λ)max (Å−1) | 0.595 |
Refinement | |
R[F2 > 2σ(F2)], wR(F2), S | 0.045, 0.094, 0.75 |
No. of reflections | 3522 |
No. of parameters | 235 |
H-atom treatment | H-atom parameters constrained |
Δρmax, Δρmin (e Å−3) | 0.13, −0.14 |
Computer programs: SMART (Siemens, 1996), SMART, SAINT (Siemens, 1996), SHELXS97 (Sheldrick, 1997a), SHELXL97 (Sheldrick, 1997a), SHELXTL (Sheldrick, 1997b), SHELXTL.
D—H···A | D—H | H···A | D···A | D—H···A |
C14—H14···Cg1i | 0.93 | 2.85 | 3.55 (3) | 132 |
C8—H8···Cg1ii | 0.93 | 3.07 | 3.79 (3) | 136 |
C21—H21···Cg2iii | 0.93 | 3.00 | 3.63 (4) | 126 |
Symmetry codes: (i) x+1/2, −y+3/2, z−1/2; (ii) −x+3/2, y−1/2, −z+1/2; (iii) x+1/2, −y+3/2, z+1/2. |
As part of our investigation of crystal structures of diamine derivatives, we report here the crystal structure of a new diamine derivative.
The molecular structure of the title compound is illustrated in Fig. 1. The bond lengths and angles are normal (Allen et al., 1987). A very closely related compound is 1,3-dibenzyl-2-phenylimidazolidine (Xia et al., 2007); it and the title compound have similar crystal structures. In the title compound, the dihedral angles between the central phenyl ring (C5—C10) and the other two phenyl rings are 78.53 (10)° (C12—C1) and 79.37 (10)° (C19—C24) (Fig. 1). Molecules are linked into chains of rings and a three-dimensional network by C—H···π hydrogen bonds (Fig. 2 and Fig. 3).