Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536807054189/cv2330sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S1600536807054189/cv2330Isup2.hkl |
CCDC reference: 672822
Key indicators
- Single-crystal X-ray study
- T = 293 K
- Mean (C-C) = 0.005 Å
- R factor = 0.069
- wR factor = 0.207
- Data-to-parameter ratio = 14.4
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 C2 PLAT241_ALERT_2_C Check High Ueq as Compared to Neighbors for C7 PLAT242_ALERT_2_C Check Low Ueq as Compared to Neighbors for C6 PLAT322_ALERT_2_C Check Hybridisation of H15B in Main Residue . ? PLAT331_ALERT_2_C Small Average Phenyl C-C Dist. C1 -C6 1.37 Ang. PLAT340_ALERT_3_C Low Bond Precision on C-C Bonds (x 1000) Ang ... 5
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 5 ALERT type 2 Indicator that the structure model may be wrong or deficient 1 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
The structure of 1,2-ethylenedioxy-bis(N-pyridin-2-ylmethyl-benzamide) was reported by Wen & Zhang (2007). For general background, see: West et al. (1992); Bunzli et al. (1984); Wen et al. (2002); Allen et al. (1987).
1,2-Dichloroethane (0.99 g, 0.01 mol) was added dropwise to a 50 ml of DMF solution containing 2-hydroxy-N-phenylmethyl-benzamide (4.54 g, 0.02 mol), K2CO3 (3 g, 0.02 mol) and KI (0.5 g), and the mixture was stirred at 328 K for 48 h. After cooling to room temperature, the mixture was filtered. DMF was removed from the filtrate under reduced pressure, and the reside was washed by column chromatography (silica gel, C2H5OH:CH3CO2C2H5 = 1:4) resulting in a colourless solid. Colourless single crystals of (I) suitable for X-ray diffraction study were obtained by slow evaporation of an ethanol–DMF (1:1 v/v) solution over a period of 25 d.
All H atoms were located in difference Fourier maps, placed in idealized positions (C—H 0.93–0.98 Å, N—H 0.86 Å) and refined as riding, with Uiso(H) = 1.2 Ueq(C, N).
Data collection: SMART (Siemens, 1996); cell refinement: SAINT (Siemens, 1996); 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 (Sheldrick, 1997b), PARST (Nardelli, 1995) and PLATON (Spek, 2003).
C30H28N2O4 | F(000) = 508 |
Mr = 480.54 | Dx = 1.285 Mg m−3 |
Monoclinic, P21/c | Mo Kα radiation, λ = 0.71073 Å |
a = 5.0620 (13) Å | Cell parameters from 934 reflections |
b = 16.401 (4) Å | θ = 2.5–21.0° |
c = 15.056 (4) Å | µ = 0.09 mm−1 |
β = 96.522 (5)° | T = 293 K |
V = 1241.9 (6) Å3 | Block, colourless |
Z = 2 | 0.42 × 0.11 × 0.05 mm |
Siemens SMART 1000 CCD area-detector diffractometer | 2341 independent reflections |
Radiation source: fine-focus sealed tube | 1425 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.035 |
Detector resolution: 8.33 pixels mm-1 | θmax = 25.7°, θmin = 1.8° |
ω scans | h = −6→5 |
Absorption correction: multi-scan (SADABS; Sheldrick, 1996) | k = −19→16 |
Tmin = 0.989, Tmax = 0.996 | l = −18→17 |
6638 measured reflections |
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)] = 0.069 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.207 | H-atom parameters constrained |
S = 1.12 | w = 1/[σ2(Fo2) + (0.1P)2] where P = (Fo2 + 2Fc2)/3 |
2341 reflections | (Δ/σ)max < 0.001 |
163 parameters | Δρmax = 0.46 e Å−3 |
0 restraints | Δρmin = −0.33 e Å−3 |
C30H28N2O4 | V = 1241.9 (6) Å3 |
Mr = 480.54 | Z = 2 |
Monoclinic, P21/c | Mo Kα radiation |
a = 5.0620 (13) Å | µ = 0.09 mm−1 |
b = 16.401 (4) Å | T = 293 K |
c = 15.056 (4) Å | 0.42 × 0.11 × 0.05 mm |
β = 96.522 (5)° |
Siemens SMART 1000 CCD area-detector diffractometer | 2341 independent reflections |
Absorption correction: multi-scan (SADABS; Sheldrick, 1996) | 1425 reflections with I > 2σ(I) |
Tmin = 0.989, Tmax = 0.996 | Rint = 0.035 |
6638 measured reflections |
R[F2 > 2σ(F2)] = 0.069 | 0 restraints |
wR(F2) = 0.207 | H-atom parameters constrained |
S = 1.12 | Δρmax = 0.46 e Å−3 |
2341 reflections | Δρmin = −0.33 e Å−3 |
163 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 | ||
O2 | 0.2700 (4) | 0.43132 (12) | 0.04071 (12) | 0.0539 (6) | |
C14 | 0.1064 (5) | 0.36654 (17) | 0.01572 (19) | 0.0478 (7) | |
C9 | −0.0472 (5) | 0.33705 (16) | 0.08071 (19) | 0.0465 (7) | |
C8 | −0.0383 (6) | 0.36742 (17) | 0.1743 (2) | 0.0490 (7) | |
N1 | 0.1948 (5) | 0.39077 (16) | 0.21573 (16) | 0.0590 (7) | |
H1A | 0.3314 | 0.3884 | 0.1867 | 0.071* | |
O1 | −0.2399 (4) | 0.36622 (16) | 0.21280 (15) | 0.0808 (8) | |
C15 | 0.4239 (5) | 0.46574 (17) | −0.02322 (18) | 0.0511 (8) | |
H15B | 0.4287 | 0.4489 | −0.0820 | 0.077* | |
H15C | 0.3052 | 0.4862 | −0.0725 | 0.077* | |
C6 | 0.3986 (6) | 0.4961 (2) | 0.3189 (2) | 0.0564 (8) | |
C10 | −0.2248 (6) | 0.27390 (19) | 0.0563 (2) | 0.0642 (9) | |
H10A | −0.3315 | 0.2546 | 0.0981 | 0.077* | |
C13 | 0.0843 (6) | 0.3322 (2) | −0.0687 (2) | 0.0622 (9) | |
H13A | 0.1851 | 0.3524 | −0.1118 | 0.075* | |
C11 | −0.2482 (8) | 0.2393 (2) | −0.0265 (3) | 0.0785 (11) | |
H11A | −0.3693 | 0.1974 | −0.0409 | 0.094* | |
C12 | −0.0899 (7) | 0.2673 (2) | −0.0889 (3) | 0.0752 (11) | |
H12A | −0.0996 | 0.2426 | −0.1448 | 0.090* | |
C5 | 0.3608 (7) | 0.5599 (2) | 0.2607 (2) | 0.0712 (10) | |
H5A | 0.2302 | 0.5562 | 0.2121 | 0.085* | |
C4 | 0.5126 (9) | 0.6296 (2) | 0.2724 (3) | 0.0817 (11) | |
H4A | 0.4830 | 0.6725 | 0.2321 | 0.098* | |
C7 | 0.2325 (7) | 0.4201 (2) | 0.3075 (2) | 0.0742 (10) | |
H7A | 0.3172 | 0.3776 | 0.3455 | 0.089* | |
H7B | 0.0599 | 0.4309 | 0.3271 | 0.089* | |
C3 | 0.7041 (8) | 0.6360 (3) | 0.3422 (3) | 0.0908 (13) | |
H3A | 0.8067 | 0.6830 | 0.3497 | 0.109* | |
C2 | 0.7467 (9) | 0.5735 (3) | 0.4013 (3) | 0.1026 (15) | |
H2A | 0.8778 | 0.5778 | 0.4496 | 0.123* | |
C1 | 0.5938 (7) | 0.5033 (2) | 0.3893 (2) | 0.0802 (11) | |
H1B | 0.6244 | 0.4605 | 0.4296 | 0.096* |
U11 | U22 | U33 | U12 | U13 | U23 | |
O2 | 0.0512 (12) | 0.0616 (13) | 0.0498 (12) | −0.0147 (10) | 0.0101 (9) | 0.0019 (10) |
C14 | 0.0360 (16) | 0.0464 (17) | 0.0594 (18) | 0.0058 (13) | −0.0022 (13) | 0.0022 (14) |
C9 | 0.0309 (14) | 0.0425 (16) | 0.0642 (18) | 0.0008 (12) | −0.0022 (13) | 0.0092 (14) |
C8 | 0.0359 (16) | 0.0505 (17) | 0.0605 (18) | −0.0012 (13) | 0.0054 (14) | 0.0150 (14) |
N1 | 0.0405 (15) | 0.0810 (19) | 0.0568 (15) | −0.0144 (13) | 0.0107 (12) | −0.0051 (13) |
O1 | 0.0422 (14) | 0.125 (2) | 0.0772 (16) | −0.0098 (13) | 0.0160 (12) | 0.0040 (14) |
C15 | 0.0481 (17) | 0.063 (2) | 0.0423 (15) | −0.0055 (14) | 0.0058 (13) | 0.0110 (13) |
C6 | 0.0483 (18) | 0.069 (2) | 0.0524 (17) | −0.0021 (15) | 0.0071 (14) | −0.0054 (16) |
C10 | 0.0497 (19) | 0.0531 (19) | 0.086 (2) | −0.0065 (15) | −0.0081 (17) | 0.0112 (18) |
C13 | 0.056 (2) | 0.071 (2) | 0.059 (2) | 0.0062 (17) | 0.0014 (15) | −0.0096 (17) |
C11 | 0.072 (3) | 0.054 (2) | 0.104 (3) | −0.0091 (18) | −0.013 (2) | −0.007 (2) |
C12 | 0.072 (2) | 0.068 (2) | 0.079 (2) | 0.015 (2) | −0.017 (2) | −0.024 (2) |
C5 | 0.066 (2) | 0.083 (3) | 0.063 (2) | −0.0006 (19) | −0.0006 (17) | −0.0004 (19) |
C4 | 0.093 (3) | 0.067 (2) | 0.088 (3) | −0.002 (2) | 0.018 (2) | −0.005 (2) |
C7 | 0.071 (2) | 0.096 (3) | 0.056 (2) | −0.019 (2) | 0.0081 (17) | 0.0016 (18) |
C3 | 0.078 (3) | 0.070 (3) | 0.126 (4) | −0.006 (2) | 0.015 (3) | −0.034 (3) |
C2 | 0.088 (3) | 0.096 (3) | 0.113 (4) | 0.007 (3) | −0.031 (3) | −0.038 (3) |
C1 | 0.084 (3) | 0.080 (3) | 0.071 (2) | 0.006 (2) | −0.019 (2) | −0.0083 (19) |
O2—C14 | 1.373 (3) | C10—H10A | 0.9300 |
O2—C15 | 1.422 (3) | C13—C12 | 1.394 (5) |
C14—C13 | 1.383 (4) | C13—H13A | 0.9300 |
C14—C9 | 1.403 (4) | C11—C12 | 1.380 (5) |
C9—C10 | 1.393 (4) | C11—H11A | 0.9300 |
C9—C8 | 1.491 (4) | C12—H12A | 0.9300 |
C8—O1 | 1.229 (3) | C5—C4 | 1.378 (5) |
C8—N1 | 1.327 (4) | C5—H5A | 0.9300 |
N1—C7 | 1.455 (4) | C4—C3 | 1.350 (5) |
N1—H1A | 0.8600 | C4—H4A | 0.9300 |
C15—C15i | 1.491 (5) | C7—H7A | 0.9700 |
C15—H15B | 0.9300 | C7—H7B | 0.9700 |
C15—H15C | 0.9599 | C3—C2 | 1.358 (6) |
C6—C5 | 1.364 (5) | C3—H3A | 0.9300 |
C6—C1 | 1.369 (4) | C2—C1 | 1.388 (6) |
C6—C7 | 1.503 (5) | C2—H2A | 0.9300 |
C10—C11 | 1.362 (5) | C1—H1B | 0.9300 |
C14—O2—C15 | 118.8 (2) | C10—C11—C12 | 119.2 (3) |
O2—C14—C13 | 123.4 (3) | C10—C11—H11A | 120.4 |
O2—C14—C9 | 116.1 (2) | C12—C11—H11A | 120.4 |
C13—C14—C9 | 120.5 (3) | C11—C12—C13 | 120.5 (3) |
C10—C9—C14 | 117.7 (3) | C11—C12—H12A | 119.8 |
C10—C9—C8 | 116.6 (3) | C13—C12—H12A | 119.8 |
C14—C9—C8 | 125.8 (3) | C6—C5—C4 | 121.2 (3) |
O1—C8—N1 | 121.7 (3) | C6—C5—H5A | 119.4 |
O1—C8—C9 | 120.1 (3) | C4—C5—H5A | 119.4 |
N1—C8—C9 | 118.1 (3) | C3—C4—C5 | 120.3 (4) |
C8—N1—C7 | 123.7 (3) | C3—C4—H4A | 119.8 |
C8—N1—H1A | 118.1 | C5—C4—H4A | 119.8 |
C7—N1—H1A | 118.1 | N1—C7—C6 | 113.2 (3) |
O2—C15—C15i | 106.0 (3) | N1—C7—H7A | 108.9 |
O2—C15—H15B | 127.0 | C6—C7—H7A | 108.9 |
C15i—C15—H15B | 127.0 | N1—C7—H7B | 108.9 |
O2—C15—H15C | 108.6 | C6—C7—H7B | 108.9 |
C15i—C15—H15C | 110.1 | H7A—C7—H7B | 107.7 |
H15B—C15—H15C | 56.6 | C4—C3—C2 | 119.9 (4) |
C5—C6—C1 | 117.9 (3) | C4—C3—H3A | 120.1 |
C5—C6—C7 | 121.8 (3) | C2—C3—H3A | 120.1 |
C1—C6—C7 | 120.3 (3) | C3—C2—C1 | 119.7 (4) |
C11—C10—C9 | 122.5 (3) | C3—C2—H2A | 120.1 |
C11—C10—H10A | 118.7 | C1—C2—H2A | 120.1 |
C9—C10—H10A | 118.7 | C6—C1—C2 | 121.0 (4) |
C14—C13—C12 | 119.6 (3) | C6—C1—H1B | 119.5 |
C14—C13—H13A | 120.2 | C2—C1—H1B | 119.5 |
C12—C13—H13A | 120.2 | ||
C15—O2—C14—C13 | 0.5 (4) | C9—C14—C13—C12 | −0.7 (4) |
C15—O2—C14—C9 | −177.9 (2) | C9—C10—C11—C12 | 0.3 (5) |
O2—C14—C9—C10 | 177.0 (2) | C10—C11—C12—C13 | −2.5 (5) |
C13—C14—C9—C10 | −1.4 (4) | C14—C13—C12—C11 | 2.7 (5) |
O2—C14—C9—C8 | −2.9 (4) | C1—C6—C5—C4 | −0.4 (5) |
C13—C14—C9—C8 | 178.7 (3) | C7—C6—C5—C4 | 179.3 (3) |
C10—C9—C8—O1 | −31.8 (4) | C6—C5—C4—C3 | 0.3 (6) |
C14—C9—C8—O1 | 148.1 (3) | C8—N1—C7—C6 | −134.0 (3) |
C10—C9—C8—N1 | 144.3 (3) | C5—C6—C7—N1 | 44.4 (4) |
C14—C9—C8—N1 | −35.8 (4) | C1—C6—C7—N1 | −135.9 (3) |
O1—C8—N1—C7 | −2.8 (5) | C5—C4—C3—C2 | −0.3 (6) |
C9—C8—N1—C7 | −178.8 (3) | C4—C3—C2—C1 | 0.4 (7) |
C14—O2—C15—C15i | 179.5 (3) | C5—C6—C1—C2 | 0.5 (5) |
C14—C9—C10—C11 | 1.7 (5) | C7—C6—C1—C2 | −179.2 (4) |
C8—C9—C10—C11 | −178.4 (3) | C3—C2—C1—C6 | −0.5 (6) |
O2—C14—C13—C12 | −179.0 (3) |
Symmetry code: (i) −x+1, −y+1, −z. |
D—H···A | D—H | H···A | D···A | D—H···A |
N1—H1A···O1ii | 0.86 | 2.19 | 2.895 (3) | 139 |
Symmetry code: (ii) x+1, y, z. |
Experimental details
Crystal data | |
Chemical formula | C30H28N2O4 |
Mr | 480.54 |
Crystal system, space group | Monoclinic, P21/c |
Temperature (K) | 293 |
a, b, c (Å) | 5.0620 (13), 16.401 (4), 15.056 (4) |
β (°) | 96.522 (5) |
V (Å3) | 1241.9 (6) |
Z | 2 |
Radiation type | Mo Kα |
µ (mm−1) | 0.09 |
Crystal size (mm) | 0.42 × 0.11 × 0.05 |
Data collection | |
Diffractometer | Siemens SMART 1000 CCD area-detector diffractometer |
Absorption correction | Multi-scan (SADABS; Sheldrick, 1996) |
Tmin, Tmax | 0.989, 0.996 |
No. of measured, independent and observed [I > 2σ(I)] reflections | 6638, 2341, 1425 |
Rint | 0.035 |
(sin θ/λ)max (Å−1) | 0.609 |
Refinement | |
R[F2 > 2σ(F2)], wR(F2), S | 0.069, 0.207, 1.12 |
No. of reflections | 2341 |
No. of parameters | 163 |
H-atom treatment | H-atom parameters constrained |
Δρmax, Δρmin (e Å−3) | 0.46, −0.33 |
Computer programs: SMART (Siemens, 1996), SAINT (Siemens, 1996), SHELXS97 (Sheldrick, 1997a), SHELXL97 (Sheldrick, 1997a), SHELXTL (Sheldrick, 1997b), PARST (Nardelli, 1995) and PLATON (Spek, 2003).
D—H···A | D—H | H···A | D···A | D—H···A |
N1—H1A···O1i | 0.86 | 2.191 | 2.895 (3) | 139.02 |
Symmetry code: (i) x+1, y, z. |
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The acyclic polyether compounds have good complexing ability and high selectivity to metal ions. Of which diamide-type acyclic polyethers have been used successfully as the active materials for ion-selective electrodes and extractants for metal ions (West et al., 1992; Bunzli et al., 1984; Wen et al., 2002). Recently, in our ongoing studies of structures and properties of the rare earth complexes with diamide-type acyclic polyethers (Wen & Zhang, 2007), a new flexible acyclic polyether compound 1,2-ethylenedioxy-bis(N-phenylmethyl-benzamide) (I), was synthesized. Herein we report the synthesis and structural characterization of (I).
The asymmetric part of the title compound contains a half of the centrosymmetric molecule, with the midpoint of the C15—C15ii bond [symmetry code: (ii): 1 - x, 1 - y, -z] located on an invesrion center (Fig. 1). All bond lengths and angles in (I) show normal values (Allen et al., 1987).
In the crystal structure, molecules are linked into chains along a axis by weak N—H···O intermolecular hydrogen bonds (Table 1 and Fig. 2).