Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536807029406/dn2200sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S1600536807029406/dn2200Isup2.hkl |
CCDC reference: 630749
Key indicators
- Single-crystal X-ray study
- T = 294 K
- Mean (C-C) = 0.003 Å
- R factor = 0.049
- wR factor = 0.141
- Data-to-parameter ratio = 16.2
checkCIF/PLATON results
No syntax errors found
Alert level C PLAT066_ALERT_1_C Predicted and Reported Transmissions Identical . ? PLAT230_ALERT_2_C Hirshfeld Test Diff for C15 - C16 .. 6.53 su PLAT230_ALERT_2_C Hirshfeld Test Diff for C17 - C23 .. 5.51 su PLAT230_ALERT_2_C Hirshfeld Test Diff for C18 - C19 .. 5.02 su PLAT230_ALERT_2_C Hirshfeld Test Diff for C21 - C32 .. 5.18 su PLAT230_ALERT_2_C Hirshfeld Test Diff for C24 - C30 .. 5.33 su PLAT241_ALERT_2_C Check High Ueq as Compared to Neighbors for C33 PLAT242_ALERT_2_C Check Low Ueq as Compared to Neighbors for C21 PLAT331_ALERT_2_C Small Average Phenyl C-C Dist. C21 -C38 1.37 Ang. PLAT480_ALERT_4_C Long H...A H-Bond Reported H4 .. O1 .. 2.64 Ang. PLAT480_ALERT_4_C Long H...A H-Bond Reported H22 .. O1 .. 2.63 Ang. PLAT480_ALERT_4_C Long H...A H-Bond Reported H20 .. O4 .. 2.61 Ang.
0 ALERT level A = In general: serious problem 0 ALERT level B = Potentially serious problem 12 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 8 ALERT type 2 Indicator that the structure model may be wrong or deficient 0 ALERT type 3 Indicator that the structure quality may be low 3 ALERT type 4 Improvement, methodology, query or suggestion 0 ALERT type 5 Informative message, check
For general background see: Renaud et al. (1999); Fujita et al. (1998); Su et al. (2002, 2003); Tümmler et al. (1979).
N-Benzylsalicylamide (0.91 g, 4.00 mmol), potassium carbonate (1.5 g, 7.2 mmol) and DMF (30 ml) were heated to ca 100 °C and 1,3-bis(benzyloxy)-5-(bromomethyl)benzene (1.53 g, 4.00 mmol) was added. The reaction mixture was stirred at 95–105 °C for 10 h. After cooling, the mixture was poured into water(100 ml). The resulted solid was subjected to column chromatography on silica gel [petroleum ether: ethyl acetate (5:1)] for separating the title compound (I), yield 89%. m. p. 84–86 °C; Analysis calculated for C35H31N1O4: C 79.37, H 5.90, N 2.64; Found: C 79.08, H 5.94, N 2.57. The crystal used for the data collection was obtained by slow evaporation of a saturated ethanol solution of (I) at room temperature.
All H atoms attached to C atoms and N atom were fixed geometrically and treated as riding with C—H = 0.93 Å (aromatic) or 0.97 Å (methylene) and N—H = 0.86 Å with Uiso(H) = 1.2Ueq(C or N).
Podand-type ligands have drawn much attention in recent years, mainly due to their selective coordinating capacity, spherodial cavities and hard binding sites, thereby stabilizing their complexes, acquiring novel coordination structure and shielding the encapsulated ion from interaction with the surroundings (Renaud et al., 1999). Among numerous podands which have demonstrated their potential use in functional supramolecular chemistry (Fujita et al., 1998; Su et al., 2002, 2003), amide-type podands are important for preparing rare earth complexes possessing strong luminescent properties. It is expected that the amide type podand ligands, which are flexible in structure and have 'terminal group effects' (Tümmler et al., 1979), will shied the encapsulated rare earth ion from interaction with the surroundings, and thus to achieve strong luminescent properties. We report here the synthesis and structure of a new amide-type podand ligand, namely 2-[3,5-bis(benzyloxy)benzyloxy]-N-benzylbenzamide (I).
In the molecule (I) there is an intramolecular hydrogen bond between the phenoxy O atom and the amide N atom (Table 1, Fig. 1). The packing is stabilized by weak C—H···O hydrogen bonding interactions (Table 1).
For general background see: Renaud et al. (1999); Fujita et al. (1998); Su et al. (2002, 2003); Tümmler et al. (1979).
Data collection: SMART (Bruker, 1997); cell refinement: SAINT (Bruker, 1997); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: SHELXTL (Bruker, 1997); software used to prepare material for publication: SHELXTL.
C35H31NO4 | F(000) = 1120 |
Mr = 529.61 | Dx = 1.235 Mg m−3 |
Monoclinic, P21/c | Melting point: 85 K |
Hall symbol: -P 2ybc | Mo Kα radiation, λ = 0.71073 Å |
a = 10.8413 (11) Å | Cell parameters from 2898 reflections |
b = 13.4524 (13) Å | θ = 2.5–22.7° |
c = 19.761 (2) Å | µ = 0.08 mm−1 |
β = 98.749 (2)° | T = 294 K |
V = 2848.5 (5) Å3 | Block, colorless |
Z = 4 | 0.31 × 0.26 × 0.25 mm |
Bruker SMART CCD area-detector diffractometer | 3315 reflections with I > 2σ(I) |
Radiation source: fine-focus sealed tube | Rint = 0.035 |
Graphite monochromator | θmax = 26.4°, θmin = 1.8° |
φ and ω scans | h = −13→12 |
15639 measured reflections | k = −16→8 |
5853 independent reflections | l = −24→24 |
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)] = 0.049 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.141 | H-atom parameters constrained |
S = 1.03 | w = 1/[σ2(Fo2) + (0.0646P)2 + 0.0363P] where P = (Fo2 + 2Fc2)/3 |
5853 reflections | (Δ/σ)max = 0.001 |
361 parameters | Δρmax = 0.15 e Å−3 |
0 restraints | Δρmin = −0.15 e Å−3 |
C35H31NO4 | V = 2848.5 (5) Å3 |
Mr = 529.61 | Z = 4 |
Monoclinic, P21/c | Mo Kα radiation |
a = 10.8413 (11) Å | µ = 0.08 mm−1 |
b = 13.4524 (13) Å | T = 294 K |
c = 19.761 (2) Å | 0.31 × 0.26 × 0.25 mm |
β = 98.749 (2)° |
Bruker SMART CCD area-detector diffractometer | 3315 reflections with I > 2σ(I) |
15639 measured reflections | Rint = 0.035 |
5853 independent reflections |
R[F2 > 2σ(F2)] = 0.049 | 0 restraints |
wR(F2) = 0.141 | H-atom parameters constrained |
S = 1.03 | Δρmax = 0.15 e Å−3 |
5853 reflections | Δρmin = −0.15 e Å−3 |
361 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 | 0.46345 (11) | 0.61754 (8) | 0.14452 (6) | 0.0577 (3) | |
O4 | 0.90358 (11) | 0.42664 (9) | 0.07570 (6) | 0.0665 (4) | |
C3 | 0.35242 (16) | 0.61863 (13) | 0.16959 (8) | 0.0514 (4) | |
C4 | 0.69374 (16) | 0.48539 (13) | 0.08748 (8) | 0.0529 (4) | |
H4 | 0.6802 | 0.4331 | 0.1162 | 0.063* | |
C5 | 0.62291 (17) | 0.63564 (13) | 0.02773 (9) | 0.0556 (5) | |
H5 | 0.5620 | 0.6841 | 0.0166 | 0.067* | |
O3 | 0.76385 (12) | 0.71197 (9) | −0.04321 (7) | 0.0737 (4) | |
C7 | 0.60291 (16) | 0.55692 (12) | 0.07024 (8) | 0.0500 (4) | |
O1 | 0.41771 (14) | 0.81493 (10) | 0.29959 (7) | 0.0822 (4) | |
C9 | 0.47838 (17) | 0.54436 (13) | 0.09333 (9) | 0.0574 (5) | |
H9A | 0.4125 | 0.5518 | 0.0546 | 0.069* | |
H9B | 0.4723 | 0.4782 | 0.1121 | 0.069* | |
N1 | 0.52907 (16) | 0.78273 (12) | 0.21593 (8) | 0.0726 (5) | |
H1 | 0.5343 | 0.7503 | 0.1790 | 0.087* | |
C11 | 0.80534 (16) | 0.49229 (13) | 0.06149 (8) | 0.0525 (4) | |
C12 | 0.82580 (17) | 0.57001 (13) | 0.01907 (8) | 0.0551 (4) | |
H12 | 0.9009 | 0.5745 | 0.0019 | 0.066* | |
C13 | 0.73461 (17) | 0.64113 (13) | 0.00210 (9) | 0.0559 (5) | |
C14 | 0.25662 (17) | 0.55232 (14) | 0.14831 (9) | 0.0629 (5) | |
H14 | 0.2673 | 0.5042 | 0.1159 | 0.075* | |
C15 | 0.43138 (19) | 0.76671 (14) | 0.24785 (9) | 0.0616 (5) | |
C16 | 0.33748 (17) | 0.69054 (13) | 0.21937 (8) | 0.0556 (5) | |
C17 | 0.80621 (18) | 0.26532 (13) | 0.04631 (9) | 0.0576 (5) | |
C18 | 0.7242 (2) | 0.85431 (13) | −0.11421 (9) | 0.0618 (5) | |
C19 | 0.67362 (18) | 0.78670 (14) | −0.06454 (10) | 0.0698 (6) | |
H19A | 0.6562 | 0.8244 | −0.0252 | 0.084* | |
H19B | 0.5965 | 0.7563 | −0.0863 | 0.084* | |
C20 | 0.14600 (19) | 0.55635 (17) | 0.17428 (11) | 0.0780 (6) | |
H20 | 0.0823 | 0.5117 | 0.1591 | 0.094* | |
C21 | 0.7162 (2) | 0.86136 (16) | 0.19042 (11) | 0.0718 (6) | |
C22 | 0.6967 (2) | 0.21968 (16) | 0.05546 (11) | 0.0738 (6) | |
H22 | 0.6639 | 0.2306 | 0.0957 | 0.089* | |
C23 | 0.87785 (19) | 0.32944 (14) | 0.10042 (10) | 0.0673 (5) | |
H23A | 0.8306 | 0.3363 | 0.1381 | 0.081* | |
H23B | 0.9561 | 0.2970 | 0.1179 | 0.081* | |
C24 | 0.6429 (2) | 0.90028 (16) | −0.16497 (10) | 0.0756 (6) | |
H24 | 0.5578 | 0.8877 | −0.1687 | 0.091* | |
C25 | 0.1297 (2) | 0.6263 (2) | 0.22263 (12) | 0.0874 (7) | |
H25 | 0.0552 | 0.6294 | 0.2404 | 0.105* | |
C26 | 0.2237 (2) | 0.69087 (17) | 0.24419 (10) | 0.0759 (6) | |
H26 | 0.2117 | 0.7377 | 0.2772 | 0.091* | |
C27 | 0.8518 (2) | 0.24915 (17) | −0.01424 (10) | 0.0778 (6) | |
H27 | 0.9253 | 0.2803 | −0.0213 | 0.093* | |
C28 | 0.7915 (3) | 0.1885 (2) | −0.06400 (12) | 0.0921 (7) | |
H28 | 0.8242 | 0.1783 | −0.1043 | 0.111* | |
C29 | 0.8491 (2) | 0.87421 (16) | −0.10963 (11) | 0.0774 (6) | |
H29 | 0.9054 | 0.8441 | −0.0755 | 0.093* | |
C30 | 0.6860 (3) | 0.96452 (18) | −0.21014 (11) | 0.0941 (8) | |
H30 | 0.6300 | 0.9952 | −0.2441 | 0.113* | |
C31 | 0.8925 (2) | 0.93881 (18) | −0.15539 (13) | 0.0927 (7) | |
H31 | 0.9775 | 0.9517 | −0.1520 | 0.111* | |
C32 | 0.7090 (2) | 0.93793 (18) | 0.14453 (14) | 0.0961 (7) | |
H32 | 0.6494 | 0.9873 | 0.1460 | 0.115* | |
C33 | 0.6274 (2) | 0.85292 (17) | 0.24101 (12) | 0.0898 (7) | |
H33A | 0.6716 | 0.8304 | 0.2847 | 0.108* | |
H33B | 0.5913 | 0.9175 | 0.2477 | 0.108* | |
C34 | 0.8104 (3) | 0.98351 (18) | −0.20541 (13) | 0.1001 (8) | |
H34 | 0.8393 | 1.0268 | −0.2362 | 0.120* | |
C35 | 0.6824 (3) | 0.14280 (17) | −0.05429 (12) | 0.0896 (7) | |
H35 | 0.6408 | 0.1017 | −0.0881 | 0.107* | |
C36 | 0.6346 (2) | 0.15801 (17) | 0.00593 (14) | 0.0876 (7) | |
H36 | 0.5611 | 0.1268 | 0.0129 | 0.105* | |
C37 | 0.8755 (3) | 0.8733 (2) | 0.09299 (14) | 0.1003 (8) | |
H37 | 0.9291 | 0.8774 | 0.0606 | 0.120* | |
C38 | 0.8054 (3) | 0.79057 (19) | 0.18585 (14) | 0.0987 (8) | |
H38 | 0.8129 | 0.7372 | 0.2161 | 0.118* | |
C39 | 0.8843 (3) | 0.7965 (2) | 0.13755 (16) | 0.1099 (9) | |
H39 | 0.9440 | 0.7474 | 0.1356 | 0.132* | |
C40 | 0.7885 (3) | 0.9438 (2) | 0.09583 (14) | 0.1065 (8) | |
H40 | 0.7816 | 0.9967 | 0.0651 | 0.128* |
U11 | U22 | U33 | U12 | U13 | U23 | |
O2 | 0.0573 (8) | 0.0602 (8) | 0.0600 (7) | −0.0018 (6) | 0.0227 (6) | −0.0197 (6) |
O4 | 0.0613 (8) | 0.0577 (8) | 0.0817 (9) | 0.0075 (6) | 0.0143 (6) | 0.0125 (7) |
C3 | 0.0518 (11) | 0.0579 (12) | 0.0463 (9) | 0.0073 (8) | 0.0135 (8) | 0.0010 (8) |
C4 | 0.0666 (12) | 0.0483 (11) | 0.0465 (9) | −0.0019 (9) | 0.0170 (8) | −0.0023 (8) |
C5 | 0.0610 (12) | 0.0477 (11) | 0.0613 (11) | 0.0064 (8) | 0.0192 (9) | −0.0050 (8) |
O3 | 0.0757 (9) | 0.0621 (9) | 0.0892 (9) | 0.0128 (7) | 0.0310 (7) | 0.0230 (7) |
C7 | 0.0591 (11) | 0.0470 (11) | 0.0470 (9) | −0.0026 (8) | 0.0176 (8) | −0.0111 (8) |
O1 | 0.1151 (12) | 0.0735 (10) | 0.0637 (8) | 0.0038 (8) | 0.0320 (8) | −0.0208 (7) |
C9 | 0.0674 (12) | 0.0543 (12) | 0.0545 (10) | −0.0039 (9) | 0.0217 (9) | −0.0153 (8) |
N1 | 0.0829 (12) | 0.0725 (12) | 0.0668 (10) | −0.0129 (9) | 0.0257 (9) | −0.0278 (8) |
C11 | 0.0564 (11) | 0.0500 (11) | 0.0515 (10) | 0.0029 (8) | 0.0096 (8) | −0.0033 (8) |
C12 | 0.0555 (11) | 0.0536 (12) | 0.0584 (10) | −0.0004 (9) | 0.0161 (8) | −0.0006 (9) |
C13 | 0.0656 (12) | 0.0470 (11) | 0.0584 (11) | 0.0002 (9) | 0.0193 (9) | 0.0029 (8) |
C14 | 0.0578 (12) | 0.0731 (14) | 0.0593 (11) | 0.0010 (10) | 0.0136 (9) | −0.0044 (9) |
C15 | 0.0799 (14) | 0.0588 (12) | 0.0491 (10) | 0.0142 (10) | 0.0193 (10) | −0.0041 (9) |
C16 | 0.0626 (12) | 0.0594 (12) | 0.0468 (9) | 0.0105 (9) | 0.0150 (9) | −0.0013 (8) |
C17 | 0.0651 (12) | 0.0518 (11) | 0.0574 (11) | 0.0141 (9) | 0.0137 (9) | 0.0091 (9) |
C18 | 0.0737 (14) | 0.0493 (12) | 0.0635 (11) | 0.0004 (10) | 0.0139 (10) | 0.0020 (9) |
C19 | 0.0677 (13) | 0.0650 (14) | 0.0788 (13) | 0.0094 (10) | 0.0181 (11) | 0.0084 (10) |
C20 | 0.0582 (13) | 0.0972 (18) | 0.0806 (14) | −0.0060 (11) | 0.0173 (11) | 0.0032 (13) |
C21 | 0.0751 (15) | 0.0579 (14) | 0.0818 (14) | −0.0103 (11) | 0.0101 (11) | −0.0148 (11) |
C22 | 0.0752 (15) | 0.0710 (15) | 0.0797 (14) | 0.0113 (11) | 0.0262 (11) | −0.0053 (11) |
C23 | 0.0769 (14) | 0.0581 (13) | 0.0669 (12) | 0.0113 (10) | 0.0113 (10) | 0.0144 (10) |
C24 | 0.0839 (15) | 0.0666 (14) | 0.0731 (13) | −0.0012 (11) | 0.0015 (12) | 0.0013 (11) |
C25 | 0.0613 (14) | 0.120 (2) | 0.0862 (16) | 0.0072 (14) | 0.0293 (12) | −0.0013 (15) |
C26 | 0.0739 (15) | 0.0928 (17) | 0.0668 (13) | 0.0154 (12) | 0.0293 (11) | −0.0109 (11) |
C27 | 0.0935 (16) | 0.0755 (15) | 0.0686 (13) | 0.0042 (12) | 0.0260 (12) | 0.0057 (12) |
C28 | 0.114 (2) | 0.0958 (19) | 0.0684 (14) | 0.0142 (16) | 0.0213 (14) | −0.0034 (13) |
C29 | 0.0805 (16) | 0.0784 (16) | 0.0747 (13) | 0.0061 (12) | 0.0158 (11) | 0.0151 (11) |
C30 | 0.130 (2) | 0.0761 (17) | 0.0725 (15) | 0.0146 (16) | 0.0022 (15) | 0.0116 (12) |
C31 | 0.0934 (18) | 0.0916 (19) | 0.0984 (17) | −0.0172 (14) | 0.0320 (15) | 0.0010 (15) |
C32 | 0.0894 (18) | 0.0799 (18) | 0.121 (2) | 0.0146 (13) | 0.0235 (15) | 0.0034 (15) |
C33 | 0.1044 (18) | 0.0791 (17) | 0.0903 (16) | −0.0238 (13) | 0.0287 (14) | −0.0321 (12) |
C34 | 0.154 (3) | 0.0682 (17) | 0.0844 (17) | −0.0095 (17) | 0.0377 (18) | 0.0134 (13) |
C35 | 0.104 (2) | 0.0737 (16) | 0.0845 (16) | 0.0211 (14) | −0.0080 (15) | −0.0187 (12) |
C36 | 0.0748 (16) | 0.0753 (16) | 0.1135 (19) | 0.0021 (12) | 0.0171 (14) | −0.0161 (14) |
C37 | 0.091 (2) | 0.111 (2) | 0.1029 (19) | −0.0104 (17) | 0.0266 (15) | −0.0028 (17) |
C38 | 0.108 (2) | 0.0773 (18) | 0.114 (2) | 0.0111 (15) | 0.0293 (16) | 0.0154 (14) |
C39 | 0.098 (2) | 0.096 (2) | 0.140 (2) | 0.0206 (15) | 0.0325 (18) | 0.0028 (19) |
C40 | 0.104 (2) | 0.101 (2) | 0.117 (2) | 0.0039 (17) | 0.0244 (17) | 0.0277 (16) |
O2—C3 | 1.3696 (19) | C21—C32 | 1.367 (3) |
O2—C9 | 1.4383 (18) | C21—C38 | 1.370 (3) |
O4—C11 | 1.379 (2) | C21—C33 | 1.494 (3) |
O4—C23 | 1.438 (2) | C22—C36 | 1.378 (3) |
C3—C14 | 1.385 (2) | C22—H22 | 0.9300 |
C3—C16 | 1.406 (2) | C23—H23A | 0.9700 |
C4—C7 | 1.382 (2) | C23—H23B | 0.9700 |
C4—C11 | 1.387 (2) | C24—C30 | 1.374 (3) |
C4—H4 | 0.9300 | C24—H24 | 0.9300 |
C5—C13 | 1.384 (2) | C25—C26 | 1.358 (3) |
C5—C7 | 1.389 (2) | C25—H25 | 0.9300 |
C5—H5 | 0.9300 | C26—H26 | 0.9300 |
O3—C13 | 1.377 (2) | C27—C28 | 1.365 (3) |
O3—C19 | 1.421 (2) | C27—H27 | 0.9300 |
C7—C9 | 1.499 (2) | C28—C35 | 1.372 (3) |
O1—C15 | 1.239 (2) | C28—H28 | 0.9300 |
C9—H9A | 0.9700 | C29—C31 | 1.387 (3) |
C9—H9B | 0.9700 | C29—H29 | 0.9300 |
N1—C15 | 1.330 (2) | C30—C34 | 1.362 (3) |
N1—C33 | 1.454 (3) | C30—H30 | 0.9300 |
N1—H1 | 0.8600 | C31—C34 | 1.365 (3) |
C11—C12 | 1.379 (2) | C31—H31 | 0.9300 |
C12—C13 | 1.380 (2) | C32—C40 | 1.388 (3) |
C12—H12 | 0.9300 | C32—H32 | 0.9300 |
C14—C20 | 1.376 (3) | C33—H33A | 0.9700 |
C14—H14 | 0.9300 | C33—H33B | 0.9700 |
C15—C16 | 1.493 (3) | C34—H34 | 0.9300 |
C16—C26 | 1.395 (3) | C35—C36 | 1.384 (3) |
C17—C22 | 1.373 (3) | C35—H35 | 0.9300 |
C17—C27 | 1.379 (2) | C36—H36 | 0.9300 |
C17—C23 | 1.496 (3) | C37—C40 | 1.345 (3) |
C18—C29 | 1.370 (3) | C37—C39 | 1.352 (3) |
C18—C24 | 1.377 (3) | C37—H37 | 0.9300 |
C18—C19 | 1.502 (3) | C38—C39 | 1.378 (3) |
C19—H19A | 0.9700 | C38—H38 | 0.9300 |
C19—H19B | 0.9700 | C39—H39 | 0.9300 |
C20—C25 | 1.371 (3) | C40—H40 | 0.9300 |
C20—H20 | 0.9300 | ||
C3—O2—C9 | 117.44 (13) | C36—C22—H22 | 119.5 |
C11—O4—C23 | 117.89 (14) | O4—C23—C17 | 112.83 (15) |
O2—C3—C14 | 122.89 (15) | O4—C23—H23A | 109.0 |
O2—C3—C16 | 117.47 (16) | C17—C23—H23A | 109.0 |
C14—C3—C16 | 119.64 (17) | O4—C23—H23B | 109.0 |
C7—C4—C11 | 119.41 (16) | C17—C23—H23B | 109.0 |
C7—C4—H4 | 120.3 | H23A—C23—H23B | 107.8 |
C11—C4—H4 | 120.3 | C30—C24—C18 | 120.8 (2) |
C13—C5—C7 | 119.20 (16) | C30—C24—H24 | 119.6 |
C13—C5—H5 | 120.4 | C18—C24—H24 | 119.6 |
C7—C5—H5 | 120.4 | C26—C25—C20 | 119.2 (2) |
C13—O3—C19 | 117.79 (14) | C26—C25—H25 | 120.4 |
C4—C7—C5 | 120.60 (16) | C20—C25—H25 | 120.4 |
C4—C7—C9 | 119.18 (15) | C25—C26—C16 | 123.3 (2) |
C5—C7—C9 | 120.05 (16) | C25—C26—H26 | 118.3 |
O2—C9—C7 | 109.86 (13) | C16—C26—H26 | 118.3 |
O2—C9—H9A | 109.7 | C28—C27—C17 | 121.6 (2) |
C7—C9—H9A | 109.7 | C28—C27—H27 | 119.2 |
O2—C9—H9B | 109.7 | C17—C27—H27 | 119.2 |
C7—C9—H9B | 109.7 | C27—C28—C35 | 119.7 (2) |
H9A—C9—H9B | 108.2 | C27—C28—H28 | 120.1 |
C15—N1—C33 | 122.63 (16) | C35—C28—H28 | 120.1 |
C15—N1—H1 | 118.7 | C18—C29—C31 | 120.6 (2) |
C33—N1—H1 | 118.7 | C18—C29—H29 | 119.7 |
C12—C11—O4 | 114.75 (16) | C31—C29—H29 | 119.7 |
C12—C11—C4 | 120.37 (16) | C34—C30—C24 | 120.3 (2) |
O4—C11—C4 | 124.87 (16) | C34—C30—H30 | 119.8 |
C11—C12—C13 | 119.86 (17) | C24—C30—H30 | 119.8 |
C11—C12—H12 | 120.1 | C34—C31—C29 | 120.0 (2) |
C13—C12—H12 | 120.1 | C34—C31—H31 | 120.0 |
O3—C13—C12 | 114.24 (16) | C29—C31—H31 | 120.0 |
O3—C13—C5 | 125.15 (16) | C21—C32—C40 | 121.6 (2) |
C12—C13—C5 | 120.56 (16) | C21—C32—H32 | 119.2 |
C20—C14—C3 | 121.16 (18) | C40—C32—H32 | 119.2 |
C20—C14—H14 | 119.4 | N1—C33—C21 | 109.56 (16) |
C3—C14—H14 | 119.4 | N1—C33—H33A | 109.8 |
O1—C15—N1 | 120.70 (19) | C21—C33—H33A | 109.8 |
O1—C15—C16 | 120.68 (18) | N1—C33—H33B | 109.8 |
N1—C15—C16 | 118.62 (15) | C21—C33—H33B | 109.8 |
C26—C16—C3 | 116.76 (18) | H33A—C33—H33B | 108.2 |
C26—C16—C15 | 117.00 (16) | C30—C34—C31 | 119.8 (2) |
C3—C16—C15 | 126.25 (16) | C30—C34—H34 | 120.1 |
C22—C17—C27 | 118.34 (19) | C31—C34—H34 | 120.1 |
C22—C17—C23 | 121.94 (17) | C28—C35—C36 | 119.8 (2) |
C27—C17—C23 | 119.70 (18) | C28—C35—H35 | 120.1 |
C29—C18—C24 | 118.50 (19) | C36—C35—H35 | 120.1 |
C29—C18—C19 | 122.06 (17) | C22—C36—C35 | 119.6 (2) |
C24—C18—C19 | 119.42 (19) | C22—C36—H36 | 120.2 |
O3—C19—C18 | 108.60 (16) | C35—C36—H36 | 120.2 |
O3—C19—H19A | 110.0 | C40—C37—C39 | 119.5 (3) |
C18—C19—H19A | 110.0 | C40—C37—H37 | 120.2 |
O3—C19—H19B | 110.0 | C39—C37—H37 | 120.2 |
C18—C19—H19B | 110.0 | C21—C38—C39 | 121.6 (2) |
H19A—C19—H19B | 108.4 | C21—C38—H38 | 119.2 |
C25—C20—C14 | 119.9 (2) | C39—C38—H38 | 119.2 |
C25—C20—H20 | 120.0 | C37—C39—C38 | 120.4 (3) |
C14—C20—H20 | 120.0 | C37—C39—H39 | 119.8 |
C32—C21—C38 | 116.7 (2) | C38—C39—H39 | 119.8 |
C32—C21—C33 | 121.6 (2) | C37—C40—C32 | 120.1 (3) |
C38—C21—C33 | 121.6 (2) | C37—C40—H40 | 119.9 |
C17—C22—C36 | 120.9 (2) | C32—C40—H40 | 119.9 |
C17—C22—H22 | 119.5 |
D—H···A | D—H | H···A | D···A | D—H···A |
N1—H1···O2 | 0.86 | 2.02 | 2.6702 (18) | 132 |
C4—H4···O1i | 0.93 | 2.64 | 3.538 (2) | 163 |
C22—H22···O1i | 0.93 | 2.63 | 3.531 (2) | 163 |
C20—H20···O4ii | 0.93 | 2.61 | 3.491 (3) | 159 |
Symmetry codes: (i) −x+1, y−1/2, −z+1/2; (ii) x−1, y, z. |
Experimental details
Crystal data | |
Chemical formula | C35H31NO4 |
Mr | 529.61 |
Crystal system, space group | Monoclinic, P21/c |
Temperature (K) | 294 |
a, b, c (Å) | 10.8413 (11), 13.4524 (13), 19.761 (2) |
β (°) | 98.749 (2) |
V (Å3) | 2848.5 (5) |
Z | 4 |
Radiation type | Mo Kα |
µ (mm−1) | 0.08 |
Crystal size (mm) | 0.31 × 0.26 × 0.25 |
Data collection | |
Diffractometer | Bruker SMART CCD area-detector |
Absorption correction | – |
No. of measured, independent and observed [I > 2σ(I)] reflections | 15639, 5853, 3315 |
Rint | 0.035 |
(sin θ/λ)max (Å−1) | 0.626 |
Refinement | |
R[F2 > 2σ(F2)], wR(F2), S | 0.049, 0.141, 1.03 |
No. of reflections | 5853 |
No. of parameters | 361 |
H-atom treatment | H-atom parameters constrained |
Δρmax, Δρmin (e Å−3) | 0.15, −0.15 |
Computer programs: SMART (Bruker, 1997), SAINT (Bruker, 1997), SAINT, SHELXS97 (Sheldrick, 1997), SHELXL97 (Sheldrick, 1997), SHELXTL (Bruker, 1997), SHELXTL.
D—H···A | D—H | H···A | D···A | D—H···A |
N1—H1···O2 | 0.86 | 2.02 | 2.6702 (18) | 131.6 |
C4—H4···O1i | 0.93 | 2.64 | 3.538 (2) | 163.2 |
C22—H22···O1i | 0.93 | 2.63 | 3.531 (2) | 163.4 |
C20—H20···O4ii | 0.93 | 2.61 | 3.491 (3) | 158.6 |
Symmetry codes: (i) −x+1, y−1/2, −z+1/2; (ii) x−1, y, z. |
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Podand-type ligands have drawn much attention in recent years, mainly due to their selective coordinating capacity, spherodial cavities and hard binding sites, thereby stabilizing their complexes, acquiring novel coordination structure and shielding the encapsulated ion from interaction with the surroundings (Renaud et al., 1999). Among numerous podands which have demonstrated their potential use in functional supramolecular chemistry (Fujita et al., 1998; Su et al., 2002, 2003), amide-type podands are important for preparing rare earth complexes possessing strong luminescent properties. It is expected that the amide type podand ligands, which are flexible in structure and have 'terminal group effects' (Tümmler et al., 1979), will shied the encapsulated rare earth ion from interaction with the surroundings, and thus to achieve strong luminescent properties. We report here the synthesis and structure of a new amide-type podand ligand, namely 2-[3,5-bis(benzyloxy)benzyloxy]-N-benzylbenzamide (I).
In the molecule (I) there is an intramolecular hydrogen bond between the phenoxy O atom and the amide N atom (Table 1, Fig. 1). The packing is stabilized by weak C—H···O hydrogen bonding interactions (Table 1).