Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536807037026/wn2158sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S1600536807037026/wn2158Isup2.hkl |
CCDC reference: 649509
Key indicators
- Single-crystal X-ray study
- T = 298 K
- Mean (C-C) = 0.005 Å
- R factor = 0.066
- wR factor = 0.161
- Data-to-parameter ratio = 14.8
checkCIF/PLATON results
No syntax errors found
Alert level C PLAT063_ALERT_3_C Crystal Probably too Large for Beam Size ....... 0.68 mm PLAT066_ALERT_1_C Predicted and Reported Transmissions Identical . ? PLAT125_ALERT_4_C No _symmetry_space_group_name_Hall Given ....... ? PLAT331_ALERT_2_C Small Average Phenyl C-C Dist. C4 -C9 1.37 Ang. 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 5 ALERT level C = Check and explain 0 ALERT level G = General alerts; check 1 ALERT type 1 CIF construction/syntax error, inconsistent or missing data 1 ALERT type 2 Indicator that the structure model may be wrong or deficient 2 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
To a solution of benzaldehyde (20 mmol) in methanol (20 ml) ethylenediamine (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 the crystal structures of ethylenediamine derivatives, we report here the crystal structure of a new ethylenediamine derivative.
The molecular structure of the title compound is illustrated in Fig. 1. In the molecule, the dihedral angles between the phenyl ring (C4–C9) and the other two phenyl rings are 78.95 (10)° (C11–C16) and 71.76 (10)° (C18–C23). The imidazolidine ring adopts a slightly distorted envelope conformation, with C3 as the flap atom. 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: SAINT (Siemens, 1996); data reduction: SAINT; 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.
C23H24N2 | F(000) = 704 |
Mr = 328.44 | Dx = 1.150 Mg m−3 |
Monoclinic, P21/n | Mo Kα radiation, λ = 0.71073 Å |
a = 6.0611 (12) Å | Cell parameters from 1633 reflections |
b = 16.0637 (16) Å | θ = 2.7–20.4° |
c = 19.494 (2) Å | µ = 0.07 mm−1 |
β = 91.545 (2)° | T = 298 K |
V = 1897.3 (5) Å3 | Block, colourless |
Z = 4 | 0.68 × 0.21 × 0.10 mm |
Bruker SMART CCD area-detector diffractometer | 3344 independent reflections |
Radiation source: fine-focus sealed tube | 1682 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→7 |
Tmin = 0.956, Tmax = 0.993 | k = −18→19 |
9261 measured reflections | l = −23→10 |
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)] = 0.066 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.161 | H-atom parameters constrained |
S = 1.03 | w = 1/[σ2(Fo2) + (0.0617P)2] where P = (Fo2 + 2Fc2)/3 |
3344 reflections | (Δ/σ)max < 0.001 |
226 parameters | Δρmax = 0.20 e Å−3 |
0 restraints | Δρmin = −0.25 e Å−3 |
C23H24N2 | V = 1897.3 (5) Å3 |
Mr = 328.44 | Z = 4 |
Monoclinic, P21/n | Mo Kα radiation |
a = 6.0611 (12) Å | µ = 0.07 mm−1 |
b = 16.0637 (16) Å | T = 298 K |
c = 19.494 (2) Å | 0.68 × 0.21 × 0.10 mm |
β = 91.545 (2)° |
Bruker SMART CCD area-detector diffractometer | 3344 independent reflections |
Absorption correction: multi-scan (SADABS; Sheldrick, 1996) | 1682 reflections with I > 2σ(I) |
Tmin = 0.956, Tmax = 0.993 | Rint = 0.073 |
9261 measured reflections |
R[F2 > 2σ(F2)] = 0.066 | 0 restraints |
wR(F2) = 0.161 | H-atom parameters constrained |
S = 1.03 | Δρmax = 0.20 e Å−3 |
3344 reflections | Δρmin = −0.25 e Å−3 |
226 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 | 0.2099 (4) | 0.13673 (13) | 0.09252 (11) | 0.0450 (6) | |
N2 | 0.2019 (4) | 0.12748 (13) | 0.20804 (12) | 0.0441 (6) | |
C1 | 0.3331 (5) | 0.06115 (17) | 0.10993 (15) | 0.0571 (9) | |
H1A | 0.4870 | 0.0670 | 0.0984 | 0.068* | |
H1B | 0.2714 | 0.0135 | 0.0856 | 0.068* | |
C2 | 0.3098 (6) | 0.05136 (19) | 0.18653 (15) | 0.0633 (10) | |
H2A | 0.2206 | 0.0030 | 0.1969 | 0.076* | |
H2B | 0.4532 | 0.0454 | 0.2093 | 0.076* | |
C3 | 0.0643 (5) | 0.15306 (16) | 0.14996 (14) | 0.0427 (7) | |
H3 | −0.0676 | 0.1179 | 0.1462 | 0.051* | |
C4 | −0.0006 (5) | 0.24356 (17) | 0.15271 (13) | 0.0408 (7) | |
C5 | 0.1595 (5) | 0.30273 (18) | 0.16510 (16) | 0.0564 (9) | |
H5 | 0.3046 | 0.2860 | 0.1736 | 0.068* | |
C6 | 0.1090 (6) | 0.3857 (2) | 0.16520 (17) | 0.0644 (10) | |
H6 | 0.2194 | 0.4247 | 0.1743 | 0.077* | |
C7 | −0.1020 (7) | 0.4116 (2) | 0.15209 (17) | 0.0650 (10) | |
H7 | −0.1354 | 0.4681 | 0.1514 | 0.078* | |
C8 | −0.2628 (6) | 0.3543 (2) | 0.14001 (19) | 0.0714 (11) | |
H8 | −0.4072 | 0.3715 | 0.1311 | 0.086* | |
C9 | −0.2119 (5) | 0.2698 (2) | 0.14094 (16) | 0.0590 (9) | |
H9 | −0.3234 | 0.2309 | 0.1335 | 0.071* | |
C10 | 0.0966 (5) | 0.13572 (18) | 0.02628 (14) | 0.0542 (9) | |
H10A | −0.0059 | 0.1821 | 0.0238 | 0.065* | |
H10B | 0.0113 | 0.0848 | 0.0221 | 0.065* | |
C11 | 0.2500 (5) | 0.14128 (16) | −0.03344 (14) | 0.0438 (8) | |
C12 | 0.4506 (5) | 0.18111 (18) | −0.02765 (16) | 0.0561 (9) | |
H12 | 0.4977 | 0.2021 | 0.0147 | 0.067* | |
C13 | 0.5840 (6) | 0.1905 (2) | −0.08390 (19) | 0.0673 (10) | |
H13 | 0.7194 | 0.2174 | −0.0792 | 0.081* | |
C14 | 0.5152 (7) | 0.1600 (2) | −0.14597 (19) | 0.0749 (11) | |
H14 | 0.6038 | 0.1662 | −0.1838 | 0.090* | |
C15 | 0.3185 (7) | 0.1206 (2) | −0.15288 (18) | 0.0757 (11) | |
H15 | 0.2724 | 0.1001 | −0.1955 | 0.091* | |
C16 | 0.1852 (6) | 0.11070 (19) | −0.09671 (16) | 0.0637 (10) | |
H16 | 0.0508 | 0.0831 | −0.1019 | 0.076* | |
C17 | 0.0859 (5) | 0.12033 (18) | 0.27187 (15) | 0.0519 (8) | |
H17A | −0.0022 | 0.0699 | 0.2706 | 0.062* | |
H17B | −0.0141 | 0.1671 | 0.2758 | 0.062* | |
C18 | 0.2370 (5) | 0.11810 (16) | 0.33424 (15) | 0.0456 (8) | |
C19 | 0.4406 (6) | 0.15655 (18) | 0.33508 (16) | 0.0561 (9) | |
H19 | 0.4898 | 0.1816 | 0.2953 | 0.067* | |
C20 | 0.5717 (6) | 0.1585 (2) | 0.3935 (2) | 0.0708 (11) | |
H20 | 0.7088 | 0.1844 | 0.3929 | 0.085* | |
C21 | 0.5023 (8) | 0.1225 (2) | 0.4528 (2) | 0.0810 (13) | |
H21 | 0.5905 | 0.1244 | 0.4926 | 0.097* | |
C22 | 0.3011 (8) | 0.0835 (2) | 0.45296 (18) | 0.0785 (12) | |
H22 | 0.2534 | 0.0583 | 0.4929 | 0.094* | |
C23 | 0.1690 (6) | 0.08140 (18) | 0.39426 (16) | 0.0599 (9) | |
H23 | 0.0326 | 0.0550 | 0.3950 | 0.072* |
U11 | U22 | U33 | U12 | U13 | U23 | |
N1 | 0.0580 (15) | 0.0464 (14) | 0.0308 (14) | 0.0057 (12) | 0.0030 (13) | −0.0005 (11) |
N2 | 0.0589 (15) | 0.0428 (14) | 0.0309 (13) | 0.0073 (12) | 0.0075 (13) | 0.0023 (11) |
C1 | 0.071 (2) | 0.0498 (18) | 0.051 (2) | 0.0065 (17) | 0.0090 (18) | −0.0026 (16) |
C2 | 0.092 (3) | 0.056 (2) | 0.042 (2) | 0.0182 (19) | 0.0050 (19) | 0.0006 (16) |
C3 | 0.0479 (17) | 0.0439 (17) | 0.0365 (17) | −0.0035 (14) | 0.0062 (15) | −0.0038 (14) |
C4 | 0.0469 (18) | 0.0426 (17) | 0.0333 (17) | 0.0022 (15) | 0.0066 (15) | 0.0023 (13) |
C5 | 0.0519 (19) | 0.0468 (19) | 0.071 (2) | −0.0017 (17) | 0.0048 (18) | −0.0011 (17) |
C6 | 0.073 (2) | 0.046 (2) | 0.074 (3) | −0.0089 (19) | 0.014 (2) | −0.0027 (18) |
C7 | 0.083 (3) | 0.048 (2) | 0.065 (2) | 0.012 (2) | 0.021 (2) | 0.0062 (17) |
C8 | 0.059 (2) | 0.066 (2) | 0.090 (3) | 0.016 (2) | 0.011 (2) | 0.013 (2) |
C9 | 0.053 (2) | 0.056 (2) | 0.068 (2) | −0.0021 (17) | 0.0016 (18) | 0.0022 (17) |
C10 | 0.057 (2) | 0.065 (2) | 0.0404 (19) | −0.0023 (16) | 0.0040 (17) | −0.0043 (16) |
C11 | 0.0579 (19) | 0.0406 (16) | 0.0332 (18) | 0.0039 (15) | 0.0031 (16) | 0.0006 (14) |
C12 | 0.069 (2) | 0.062 (2) | 0.0376 (19) | −0.0042 (18) | −0.0005 (18) | 0.0058 (16) |
C13 | 0.070 (2) | 0.070 (2) | 0.063 (2) | −0.0016 (19) | 0.016 (2) | 0.023 (2) |
C14 | 0.094 (3) | 0.079 (3) | 0.053 (3) | 0.020 (2) | 0.028 (2) | 0.012 (2) |
C15 | 0.107 (3) | 0.081 (3) | 0.039 (2) | 0.008 (3) | 0.009 (2) | −0.0122 (19) |
C16 | 0.083 (2) | 0.065 (2) | 0.044 (2) | −0.0012 (19) | 0.003 (2) | −0.0088 (18) |
C17 | 0.062 (2) | 0.0514 (19) | 0.0423 (18) | −0.0030 (16) | 0.0094 (17) | 0.0040 (15) |
C18 | 0.063 (2) | 0.0355 (16) | 0.0381 (18) | 0.0062 (16) | 0.0047 (16) | −0.0026 (14) |
C19 | 0.070 (2) | 0.0514 (19) | 0.047 (2) | 0.0022 (18) | 0.0057 (19) | −0.0057 (15) |
C20 | 0.074 (3) | 0.070 (2) | 0.067 (3) | 0.0099 (19) | −0.010 (2) | −0.018 (2) |
C21 | 0.109 (3) | 0.080 (3) | 0.052 (3) | 0.019 (3) | −0.024 (3) | −0.012 (2) |
C22 | 0.120 (3) | 0.071 (3) | 0.044 (2) | 0.014 (3) | 0.005 (2) | 0.0061 (18) |
C23 | 0.083 (2) | 0.055 (2) | 0.042 (2) | 0.0034 (18) | 0.006 (2) | 0.0068 (17) |
N1—C10 | 1.446 (3) | C10—H10B | 0.9700 |
N1—C1 | 1.460 (3) | C11—C16 | 1.375 (4) |
N1—C3 | 1.468 (3) | C11—C12 | 1.376 (4) |
N2—C3 | 1.448 (3) | C12—C13 | 1.388 (4) |
N2—C17 | 1.450 (4) | C12—H12 | 0.9300 |
N2—C2 | 1.454 (3) | C13—C14 | 1.360 (4) |
C1—C2 | 1.512 (4) | C13—H13 | 0.9300 |
C1—H1A | 0.9700 | C14—C15 | 1.353 (5) |
C1—H1B | 0.9700 | C14—H14 | 0.9300 |
C2—H2A | 0.9700 | C15—C16 | 1.387 (5) |
C2—H2B | 0.9700 | C15—H15 | 0.9300 |
C3—C4 | 1.507 (4) | C16—H16 | 0.9300 |
C3—H3 | 0.9800 | C17—C18 | 1.503 (4) |
C4—C9 | 1.362 (4) | C17—H17A | 0.9700 |
C4—C5 | 1.375 (4) | C17—H17B | 0.9700 |
C5—C6 | 1.368 (4) | C18—C19 | 1.380 (4) |
C5—H5 | 0.9300 | C18—C23 | 1.383 (4) |
C6—C7 | 1.362 (4) | C19—C20 | 1.372 (4) |
C6—H6 | 0.9300 | C19—H19 | 0.9300 |
C7—C8 | 1.357 (4) | C20—C21 | 1.369 (5) |
C7—H7 | 0.9300 | C20—H20 | 0.9300 |
C8—C9 | 1.392 (4) | C21—C22 | 1.371 (5) |
C8—H8 | 0.9300 | C21—H21 | 0.9300 |
C9—H9 | 0.9300 | C22—C23 | 1.379 (4) |
C10—C11 | 1.512 (4) | C22—H22 | 0.9300 |
C10—H10A | 0.9700 | C23—H23 | 0.9300 |
C10—N1—C1 | 115.2 (2) | N1—C10—H10B | 108.9 |
C10—N1—C3 | 113.7 (2) | C11—C10—H10B | 108.9 |
C1—N1—C3 | 106.6 (2) | H10A—C10—H10B | 107.7 |
C3—N2—C17 | 114.3 (2) | C16—C11—C12 | 118.1 (3) |
C3—N2—C2 | 105.5 (2) | C16—C11—C10 | 120.2 (3) |
C17—N2—C2 | 114.4 (2) | C12—C11—C10 | 121.6 (3) |
N1—C1—C2 | 104.8 (2) | C11—C12—C13 | 121.2 (3) |
N1—C1—H1A | 110.8 | C11—C12—H12 | 119.4 |
C2—C1—H1A | 110.8 | C13—C12—H12 | 119.4 |
N1—C1—H1B | 110.8 | C14—C13—C12 | 119.5 (3) |
C2—C1—H1B | 110.8 | C14—C13—H13 | 120.2 |
H1A—C1—H1B | 108.9 | C12—C13—H13 | 120.2 |
N2—C2—C1 | 104.6 (2) | C15—C14—C13 | 120.3 (4) |
N2—C2—H2A | 110.8 | C15—C14—H14 | 119.8 |
C1—C2—H2A | 110.8 | C13—C14—H14 | 119.8 |
N2—C2—H2B | 110.8 | C14—C15—C16 | 120.4 (3) |
C1—C2—H2B | 110.8 | C14—C15—H15 | 119.8 |
H2A—C2—H2B | 108.9 | C16—C15—H15 | 119.8 |
N2—C3—N1 | 101.5 (2) | C11—C16—C15 | 120.6 (3) |
N2—C3—C4 | 113.0 (2) | C11—C16—H16 | 119.7 |
N1—C3—C4 | 111.2 (2) | C15—C16—H16 | 119.7 |
N2—C3—H3 | 110.2 | N2—C17—C18 | 113.4 (2) |
N1—C3—H3 | 110.2 | N2—C17—H17A | 108.9 |
C4—C3—H3 | 110.2 | C18—C17—H17A | 108.9 |
C9—C4—C5 | 118.1 (3) | N2—C17—H17B | 108.9 |
C9—C4—C3 | 122.5 (3) | C18—C17—H17B | 108.9 |
C5—C4—C3 | 119.3 (2) | H17A—C17—H17B | 107.7 |
C6—C5—C4 | 121.1 (3) | C19—C18—C23 | 117.9 (3) |
C6—C5—H5 | 119.4 | C19—C18—C17 | 121.6 (3) |
C4—C5—H5 | 119.4 | C23—C18—C17 | 120.4 (3) |
C7—C6—C5 | 120.5 (3) | C20—C19—C18 | 121.2 (3) |
C7—C6—H6 | 119.8 | C20—C19—H19 | 119.4 |
C5—C6—H6 | 119.8 | C18—C19—H19 | 119.4 |
C8—C7—C6 | 119.4 (3) | C21—C20—C19 | 120.5 (4) |
C8—C7—H7 | 120.3 | C21—C20—H20 | 119.7 |
C6—C7—H7 | 120.3 | C19—C20—H20 | 119.7 |
C7—C8—C9 | 120.1 (3) | C20—C21—C22 | 119.2 (4) |
C7—C8—H8 | 119.9 | C20—C21—H21 | 120.4 |
C9—C8—H8 | 119.9 | C22—C21—H21 | 120.4 |
C4—C9—C8 | 120.8 (3) | C21—C22—C23 | 120.4 (4) |
C4—C9—H9 | 119.6 | C21—C22—H22 | 119.8 |
C8—C9—H9 | 119.6 | C23—C22—H22 | 119.8 |
N1—C10—C11 | 113.6 (2) | C22—C23—C18 | 120.8 (3) |
N1—C10—H10A | 108.9 | C22—C23—H23 | 119.6 |
C11—C10—H10A | 108.9 | C18—C23—H23 | 119.6 |
C10—N1—C1—C2 | −145.1 (3) | C1—N1—C10—C11 | −71.5 (3) |
C3—N1—C1—C2 | −17.9 (3) | C3—N1—C10—C11 | 165.1 (2) |
C3—N2—C2—C1 | 30.7 (3) | N1—C10—C11—C16 | 155.5 (3) |
C17—N2—C2—C1 | 157.1 (2) | N1—C10—C11—C12 | −28.5 (4) |
N1—C1—C2—N2 | −7.5 (3) | C16—C11—C12—C13 | 0.2 (4) |
C17—N2—C3—N1 | −167.9 (2) | C10—C11—C12—C13 | −175.9 (3) |
C2—N2—C3—N1 | −41.4 (3) | C11—C12—C13—C14 | 0.2 (5) |
C17—N2—C3—C4 | 72.8 (3) | C12—C13—C14—C15 | −0.2 (5) |
C2—N2—C3—C4 | −160.7 (2) | C13—C14—C15—C16 | −0.2 (5) |
C10—N1—C3—N2 | 164.5 (2) | C12—C11—C16—C15 | −0.5 (4) |
C1—N1—C3—N2 | 36.5 (3) | C10—C11—C16—C15 | 175.5 (3) |
C10—N1—C3—C4 | −75.0 (3) | C14—C15—C16—C11 | 0.6 (5) |
C1—N1—C3—C4 | 157.0 (2) | C3—N2—C17—C18 | −163.5 (2) |
N2—C3—C4—C9 | −132.9 (3) | C2—N2—C17—C18 | 74.8 (3) |
N1—C3—C4—C9 | 113.6 (3) | N2—C17—C18—C19 | 28.4 (4) |
N2—C3—C4—C5 | 49.4 (4) | N2—C17—C18—C23 | −155.7 (3) |
N1—C3—C4—C5 | −64.1 (3) | C23—C18—C19—C20 | 0.0 (4) |
C9—C4—C5—C6 | −0.4 (5) | C17—C18—C19—C20 | 176.0 (3) |
C3—C4—C5—C6 | 177.3 (3) | C18—C19—C20—C21 | −0.4 (5) |
C4—C5—C6—C7 | −0.8 (5) | C19—C20—C21—C22 | 0.8 (5) |
C5—C6—C7—C8 | 1.1 (5) | C20—C21—C22—C23 | −0.8 (5) |
C6—C7—C8—C9 | −0.1 (5) | C21—C22—C23—C18 | 0.3 (5) |
C5—C4—C9—C8 | 1.4 (5) | C19—C18—C23—C22 | 0.1 (4) |
C3—C4—C9—C8 | −176.2 (3) | C17—C18—C23—C22 | −176.0 (3) |
C7—C8—C9—C4 | −1.2 (5) |
D—H···A | D—H | H···A | D···A | D—H···A |
C7—H7···Cg1i | 0.93 | 3.07 | 3.76 (2) | 132 |
C20—H20···Cg2ii | 0.93 | 2.85 | 3.59 (2) | 137 |
Symmetry codes: (i) −x+1/2, y+1/2, −z+1/2; (ii) x+1/2, −y+1/2, z+1/2. |
Experimental details
Crystal data | |
Chemical formula | C23H24N2 |
Mr | 328.44 |
Crystal system, space group | Monoclinic, P21/n |
Temperature (K) | 298 |
a, b, c (Å) | 6.0611 (12), 16.0637 (16), 19.494 (2) |
β (°) | 91.545 (2) |
V (Å3) | 1897.3 (5) |
Z | 4 |
Radiation type | Mo Kα |
µ (mm−1) | 0.07 |
Crystal size (mm) | 0.68 × 0.21 × 0.10 |
Data collection | |
Diffractometer | Bruker SMART CCD area-detector |
Absorption correction | Multi-scan (SADABS; Sheldrick, 1996) |
Tmin, Tmax | 0.956, 0.993 |
No. of measured, independent and observed [I > 2σ(I)] reflections | 9261, 3344, 1682 |
Rint | 0.073 |
(sin θ/λ)max (Å−1) | 0.595 |
Refinement | |
R[F2 > 2σ(F2)], wR(F2), S | 0.066, 0.161, 1.03 |
No. of reflections | 3344 |
No. of parameters | 226 |
H-atom treatment | H-atom parameters constrained |
Δρmax, Δρmin (e Å−3) | 0.20, −0.25 |
Computer programs: SMART (Siemens, 1996), SAINT (Siemens, 1996), SAINT, SHELXS97 (Sheldrick, 1997a), SHELXL97 (Sheldrick, 1997a), SHELXTL (Sheldrick, 1997b), SHELXTL.
D—H···A | D—H | H···A | D···A | D—H···A |
C7—H7···Cg1i | 0.93 | 3.07 | 3.76 (2) | 132 |
C20—H20···Cg2ii | 0.93 | 2.85 | 3.59 (2) | 137 |
Symmetry codes: (i) −x+1/2, y+1/2, −z+1/2; (ii) x+1/2, −y+1/2, z+1/2. |
As part of our investigation of the crystal structures of ethylenediamine derivatives, we report here the crystal structure of a new ethylenediamine derivative.
The molecular structure of the title compound is illustrated in Fig. 1. In the molecule, the dihedral angles between the phenyl ring (C4–C9) and the other two phenyl rings are 78.95 (10)° (C11–C16) and 71.76 (10)° (C18–C23). The imidazolidine ring adopts a slightly distorted envelope conformation, with C3 as the flap atom. Molecules are linked into chains of rings and a three dimensional network by C—H···π hydrogen bonds (Fig. 2 and Fig. 3).