N-Benzyl-2-[3,5-bis­(benz­yloxy)benz­yloxy]benzamide

Tang, Z.-H.; Tang, Y.; Cao, X.-P.

doi:10.1107/S1600536807029406

N-Benzyl-2-[3,5-bis(benzyloxy)benzyloxy]benzamide

The title compound, C₃₅H₃₁NO₄, which is a new amide podand ligand, contains an intramolecular hydrogen bond between the phenoxy O atom and the amide N atom. The packing is stabilized by weak C—H

O hydrogen-bonding interactions.

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Supporting information

	Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536807029406/dn2200sup1.cif Contains datablocks global, I
	Structure factor file (CIF format) https://doi.org/10.1107/S1600536807029406/dn2200Isup2.hkl Contains datablock I

CCDC reference: 630749

checkCIF report

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

Comment top

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).

Related literature top

For general background see: Renaud et al. (1999); Fujita et al. (1998); Su et al. (2002, 2003); Tümmler et al. (1979).

Experimental top

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.

Structure description top

For general background see: Renaud et al. (1999); Fujita et al. (1998); Su et al. (2002, 2003); Tümmler et al. (1979).

Computing details top

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.

Figures top

Fig. 1. Molecular view of (I), with the atom-numbering scheme. Ellipsoids are drawjn at the 30% probability level. H atoms are shown as small spheres of arbitrary radii. The intramolecular H bond is shown as dashed line.

N-Benzyl-2-[3,5-bis(benzyloxy)benzyloxy]benzamide top

Crystal data top

C₃₅H₃₁NO₄	F(000) = 1120
M_r = 529.61	D_x = 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

Data collection top

Bruker SMART CCD area-detector diffractometer	3315 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	R_int = 0.035
Graphite monochromator	θ_max = 26.4°, θ_min = 1.8°
φ and ω scans	h = −13→12
15639 measured reflections	k = −16→8
5853 independent reflections	l = −24→24

Refinement top

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(F_o²) + (0.0646P)² + 0.0363P] where P = (F_o² + 2F_c²)/3
5853 reflections	(Δ/σ)_max = 0.001
361 parameters	Δρ_max = 0.15 e Å⁻³
0 restraints	Δρ_min = −0.15 e Å⁻³

Crystal data top

C₃₅H₃₁NO₄	V = 2848.5 (5) Å³
M_r = 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)°

Data collection top

Bruker SMART CCD area-detector diffractometer	3315 reflections with I > 2σ(I)
15639 measured reflections	R_int = 0.035
5853 independent reflections

Refinement top

R[F² > 2σ(F²)] = 0.049	0 restraints
wR(F²) = 0.141	H-atom parameters constrained
S = 1.03	Δρ_max = 0.15 e Å⁻³
5853 reflections	Δρ_min = −0.15 e Å⁻³
361 parameters

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.

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.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å²) top

	x	y	z	U_iso*/U_eq
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*

Atomic displacement parameters (Å²) top

	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)

Geometric parameters (Å, º) top

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

Hydrogen-bond geometry (Å, º) top

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
M_r	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
R_int	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
Δρ_max, Δρ_min (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.