2,2′-Bis(4-nitro­phen­oxy)-1,1′-binaphth­yl

Liang, W.-X.; Qu, Z.-R.

doi:10.1107/S1600536808016061

organic compounds

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ISSN: 2056-9890

Volume 64| Part 7| July 2008| Page o1198

doi:10.1107/S1600536808016061

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2,2′-Bis(4-nitrophenoxy)-1,1′-binaphthyl

Wen-Xian Liang ^a and Zhi-Rong Qu ^a ^*

^aOrdered Matter Science Research Center, College of Chemistry and Chemical Engineering, Southeast University, Nanjing 210096, People's Republic of China
^*Correspondence e-mail: quzr@seu.edu.cn

(Received 20 May 2008; accepted 28 May 2008; online 7 June 2008)

The title compound, C₃₂H₂₀N₂O₆, was synthesized by the reaction of 1,1′-binaphthyl-2,2′-diol and 4-nitrophenol in the presence of K₂CO₃. The two naphthalene systems make a dihedral angle of 73.70 (5)°. The crystal packing involves molecules connected by C—H⋯O hydrogen bonds into a chain along the c axis.

Related literature

For the chemistry of 1,1′-binaphthyl-2,2′-diol, see: Hiroshi et al. (2005 ); Minatti & Dötz (2005 ); Pu (1998 ); Periasamy et al. (1998 ).

Experimental

Crystal data

C₃₂H₂₀N₂O₆
M_r = 528.50
Monoclinic, P 2₁ /c
a = 7.6159 (9) Å
b = 24.810 (3) Å
c = 13.5022 (15) Å
β = 95.790 (3)°
V = 2538.3 (5) Å³
Z = 4
Mo Kα radiation
μ = 0.10 mm⁻¹
T = 296 (2) K
0.03 × 0.03 × 0.02 mm

Data collection

Bruker SMART APEX CCD area-detector diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2000 ) T_min = 0.988, T_max = 0.990
13574 measured reflections
4971 independent reflections
2521 reflections with I > 2σ(I)
R_int = 0.060

Refinement

R[F² > 2σ(F²)] = 0.054
wR(F²) = 0.114
S = 0.85
4971 reflections
361 parameters
H-atom parameters constrained
Δρ_max = 0.13 e Å⁻³
Δρ_min = −0.20 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C16—H16A⋯O2ⁱ	0.93	2.54	3.425 (3)	159
C32—H32A⋯O6ⁱⁱ	0.93	2.45	3.360 (3)	165
Symmetry codes: (i) x+1, y, z; (ii) $[x, -y+{\script{1\over 2}}, z+{\script{1\over 2}}]$ .

Data collection: SMART (Bruker, 2000); cell refinement: SAINT (Bruker, 2000); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXTL.

Supporting information

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536808016061/kp2173sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536808016061/kp2173Isup2.hkl

checkCIF report

Comment top

Axially chiral 2,2'-substituted-1,1'-binaphthyls have been extensively applied in many asymmetric processes, due to their highly stable chiral configuration with C₂ symmetry (Pu, 1998). Chemists have synthesized a great number of 2,2'-substituted-1,1'-binaphthyls which have been used in asymmetric catalysis and chiral recognition (Periasamy et al., 1998). Herein we report the structure of title compound, 2,2'-substituted-1,1'-binaphthyls (Fig. 1).

In the structure of the title compoud geometric parameters are in the usual ranges. The two naphthalene rings make a dihedral angle of 73.70 (5)°. The dihedral angles between the two 4-nitrobenzene rings and the two naphthalene rings directly attached to them (ring C11–C16 between ring C1–C10 76.42 (7)° and ring C27–C32 between ring C17–C26 81.99 (7)°, respectivley) are in synclinal range. The dihedral angles between the two 4-nitrobenzene rings and the two naphthalene rings, not directly attached to them, are remarkably different: between C27–C32 and C1–C10 is 22.62 (5)° and between C11–C16 and C17–C26 is 81.87 (6)°. The two aromatic rings with the smallest dihedral angle of 22.62 (5)°) exhibit weak intramolecular π–π interaction with the separation distance 3.694 (16) an 3.8227 (17) Å between the ring centroids of the 4-nitrobenzene rings and the two six-membered rings of the naphthalene ring. In the crystal structure no classical hydrogen bond is found. The crystal packing involves C—H···O hydrogen bonds generating chain along the c axis (Table 1, Fig. 2) and a weak C—H···π interaction [C20—H20···Cg (the ring C11, C12, C13, C14, C15, C16 with symmetry opeartion x, -y + 1,-z + 1) of 3.814 (3) Å].

Related literature top

For the chemistry of 1,1'-binaphthyl-2,2'-diol, see: Hiroshi et al. (2005); Minatti & Dötz (2005); Pu (1998); Periasamy et al. (1998).

Experimental top

1,1'-binaphthyl-2,2'-diol (1 mmol, 0.29 g) and 4-nitrophenol (2 mmol, 0.28 g) were dissolved in acetone (25 ml) in the presence of K₂CO₃ (1 mmol, 0.14 g) and refluxed for 2–3 days. After the mixture was cooled to room temperature, the solution was filtered and rotated in vacuum affording yellow precipitate of compound I. The crude product was recrystallized by slowly evaporating ethanol to yield colourless crystals.

Computing details top

Data collection: SMART (Bruker, 2000); cell refinement: SAINT (Bruker, 2000); data reduction: SAINT (Bruker, 2000); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXTL (Sheldrick, 2008).

Figures top

Fig. 1. A view of the title compound with the atomic numbering scheme. Displacement ellipsoids were drawn at the 30% probability level. H atoms have been omitted for clarity.

2,2'-Bis(4-nitrophenoxy)-1,1'-binaphthyl top

Crystal data top

C₃₂H₂₀N₂O₆	F(000) = 1096
M_r = 528.50	D_x = 1.383 Mg m⁻³
Monoclinic, P2₁/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 1979 reflections
a = 7.6159 (9) Å	θ = 3.1–27.3°
b = 24.810 (3) Å	µ = 0.10 mm⁻¹
c = 13.5022 (15) Å	T = 296 K
β = 95.790 (3)°	Block, colourless
V = 2538.3 (5) Å³	0.03 × 0.03 × 0.02 mm
Z = 4

Data collection top

Bruker SMART APEX CCD area-detector diffractometer	4971 independent reflections
Radiation source: fine-focus sealed tube	2521 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.060
ϕ and ω scans	θ_max = 26.0°, θ_min = 1.7°
Absorption correction: multi-scan (SADABS; Bruker, 2000)	h = −9→9
T_min = 0.988, T_max = 0.990	k = −23→30
13574 measured reflections	l = −16→14

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)] = 0.054	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.114	H-atom parameters constrained
S = 0.86	w = 1/[σ²(F_o²) + (0.036P)²] where P = (F_o² + 2F_c²)/3
4971 reflections	(Δ/σ)_max < 0.001
361 parameters	Δρ_max = 0.13 e Å⁻³
0 restraints	Δρ_min = −0.21 e Å⁻³

Crystal data top

C₃₂H₂₀N₂O₆	V = 2538.3 (5) Å³
M_r = 528.50	Z = 4
Monoclinic, P2₁/c	Mo Kα radiation
a = 7.6159 (9) Å	µ = 0.10 mm⁻¹
b = 24.810 (3) Å	T = 296 K
c = 13.5022 (15) Å	0.03 × 0.03 × 0.02 mm
β = 95.790 (3)°

Data collection top

Bruker SMART APEX CCD area-detector diffractometer	4971 independent reflections
Absorption correction: multi-scan (SADABS; Bruker, 2000)	2521 reflections with I > 2σ(I)
T_min = 0.988, T_max = 0.990	R_int = 0.060
13574 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.054	0 restraints
wR(F²) = 0.114	H-atom parameters constrained
S = 0.86	Δρ_max = 0.13 e Å⁻³
4971 reflections	Δρ_min = −0.21 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
O4	1.3508 (2)	0.39839 (7)	0.26199 (13)	0.0562 (5)
O1	0.9879 (2)	0.43838 (7)	0.17323 (12)	0.0553 (5)
N1	0.4540 (3)	0.59046 (10)	0.10343 (16)	0.0583 (7)
C25	1.0230 (4)	0.40498 (9)	0.44518 (18)	0.0446 (7)
C8	1.0031 (3)	0.36017 (9)	0.27505 (17)	0.0397 (6)
C24	1.1008 (3)	0.39169 (9)	0.35680 (17)	0.0399 (6)
C11	0.8489 (4)	0.47360 (10)	0.15533 (17)	0.0448 (7)
C17	1.2690 (4)	0.40833 (9)	0.34837 (19)	0.0448 (7)
C23	0.8491 (4)	0.39068 (10)	0.46109 (19)	0.0529 (7)
H23A	0.7797	0.3720	0.4118	0.063*
C12	0.6795 (4)	0.46179 (10)	0.17407 (18)	0.0535 (7)
H12A	0.6527	0.4279	0.1980	0.064*
C7	1.0293 (4)	0.27455 (11)	0.37128 (19)	0.0553 (8)
H7A	1.0782	0.2931	0.4273	0.066*
O3	0.4934 (3)	0.63407 (8)	0.07056 (14)	0.0734 (6)
C9	0.9767 (3)	0.30318 (10)	0.28363 (18)	0.0445 (7)
C14	0.5925 (4)	0.54981 (11)	0.12233 (18)	0.0479 (7)
C3	0.8464 (4)	0.30174 (12)	0.1116 (2)	0.0641 (8)
H3A	0.7937	0.2828	0.0570	0.077*
C1	0.9496 (3)	0.38393 (10)	0.18595 (19)	0.0467 (7)
C27	1.3749 (3)	0.34527 (11)	0.23632 (19)	0.0462 (7)
N2	1.4260 (4)	0.18672 (11)	0.1414 (2)	0.0768 (8)
C15	0.7607 (4)	0.56203 (11)	0.10407 (18)	0.0558 (8)
H15A	0.7872	0.5961	0.0808	0.067*
C2	0.8700 (4)	0.35544 (12)	0.10426 (19)	0.0608 (8)
H2A	0.8336	0.3733	0.0452	0.073*
C22	0.7803 (4)	0.40373 (11)	0.5478 (2)	0.0671 (9)
H22A	0.6655	0.3937	0.5571	0.081*
C32	1.4198 (3)	0.30571 (11)	0.30582 (19)	0.0531 (7)
H32A	1.4369	0.3143	0.3732	0.064*
O2	0.3041 (3)	0.57870 (8)	0.12092 (16)	0.0825 (7)
C10	0.9002 (4)	0.27407 (11)	0.2002 (2)	0.0526 (7)
C16	0.8915 (4)	0.52370 (11)	0.12019 (17)	0.0540 (7)
H16A	1.0066	0.5315	0.1076	0.065*
C26	1.1244 (4)	0.43468 (10)	0.52074 (19)	0.0528 (7)
C18	1.3671 (4)	0.43793 (10)	0.4217 (2)	0.0601 (8)
H18A	1.4807	0.4491	0.4122	0.072*
C13	0.5496 (4)	0.50002 (11)	0.15740 (19)	0.0578 (8)
H13A	0.4343	0.4923	0.1696	0.069*
C31	1.4392 (4)	0.25318 (11)	0.27459 (19)	0.0539 (7)
H31A	1.4698	0.2259	0.3203	0.065*
C19	1.2974 (4)	0.45038 (11)	0.5068 (2)	0.0663 (9)
H19A	1.3642	0.4695	0.5564	0.080*
C30	1.4125 (4)	0.24221 (11)	0.1749 (2)	0.0527 (7)
C4	0.8843 (4)	0.21737 (12)	0.2078 (2)	0.0721 (9)
H4A	0.8363	0.1978	0.1529	0.086*
O5	1.4527 (3)	0.15122 (9)	0.20191 (16)	0.0954 (8)
C20	1.0481 (5)	0.44692 (12)	0.6088 (2)	0.0767 (10)
H20A	1.1141	0.4658	0.6591	0.092*
C29	1.3761 (4)	0.28167 (12)	0.10560 (19)	0.0634 (8)
H29A	1.3643	0.2733	0.0381	0.076*
C28	1.3571 (3)	0.33380 (11)	0.13642 (19)	0.0564 (8)
H28A	1.3323	0.3611	0.0900	0.068*
C5	0.9374 (5)	0.19142 (12)	0.2932 (3)	0.0820 (10)
H5A	0.9256	0.1542	0.2969	0.098*
O6	1.4102 (4)	0.17823 (9)	0.05245 (17)	0.1275 (11)
C6	1.0096 (4)	0.22003 (12)	0.3755 (2)	0.0680 (9)
H6A	1.0451	0.2018	0.4344	0.082*
C21	0.8817 (5)	0.43195 (13)	0.6221 (2)	0.0774 (11)
H21A	0.8347	0.4405	0.6811	0.093*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
O4	0.0586 (14)	0.0454 (12)	0.0676 (12)	−0.0072 (9)	0.0207 (10)	0.0062 (10)
O1	0.0477 (13)	0.0515 (12)	0.0657 (12)	−0.0035 (10)	0.0005 (10)	0.0137 (10)
N1	0.0579 (19)	0.0617 (18)	0.0550 (15)	0.0040 (15)	0.0045 (14)	0.0064 (14)
C25	0.0507 (19)	0.0348 (15)	0.0473 (16)	0.0051 (13)	0.0006 (14)	0.0039 (13)
C8	0.0376 (17)	0.0417 (16)	0.0406 (15)	−0.0034 (12)	0.0087 (12)	−0.0034 (13)
C24	0.0422 (18)	0.0337 (15)	0.0429 (15)	−0.0030 (12)	−0.0007 (13)	0.0037 (12)
C11	0.0453 (19)	0.0494 (17)	0.0387 (15)	−0.0052 (14)	−0.0014 (13)	0.0036 (13)
C17	0.0462 (19)	0.0353 (15)	0.0519 (17)	−0.0057 (13)	−0.0001 (15)	0.0033 (13)
C23	0.055 (2)	0.0523 (18)	0.0518 (17)	0.0060 (14)	0.0094 (15)	0.0038 (14)
C12	0.050 (2)	0.0451 (18)	0.0666 (19)	−0.0043 (15)	0.0126 (16)	0.0111 (15)
C7	0.060 (2)	0.0493 (18)	0.0572 (18)	−0.0070 (15)	0.0095 (15)	0.0004 (15)
O3	0.0901 (18)	0.0586 (14)	0.0727 (13)	0.0070 (12)	0.0136 (12)	0.0199 (12)
C9	0.0418 (18)	0.0441 (17)	0.0490 (16)	−0.0071 (13)	0.0113 (13)	−0.0053 (14)
C14	0.049 (2)	0.0480 (18)	0.0461 (16)	−0.0017 (15)	0.0038 (14)	0.0031 (14)
C3	0.058 (2)	0.077 (2)	0.0542 (19)	−0.0067 (18)	−0.0057 (16)	−0.0206 (18)
C1	0.0399 (18)	0.0475 (18)	0.0529 (17)	−0.0023 (14)	0.0056 (14)	−0.0026 (15)
C27	0.0383 (17)	0.0463 (18)	0.0551 (17)	−0.0013 (13)	0.0094 (14)	0.0056 (15)
N2	0.093 (2)	0.067 (2)	0.0689 (19)	0.0145 (17)	0.0008 (17)	−0.0064 (17)
C15	0.057 (2)	0.0519 (18)	0.0573 (18)	−0.0111 (16)	0.0026 (16)	0.0150 (15)
C2	0.055 (2)	0.075 (2)	0.0502 (17)	0.0011 (17)	−0.0048 (15)	−0.0006 (17)
C22	0.071 (2)	0.069 (2)	0.065 (2)	0.0214 (18)	0.0218 (19)	0.0203 (18)
C32	0.056 (2)	0.0562 (19)	0.0463 (16)	−0.0008 (15)	0.0037 (14)	0.0003 (15)
O2	0.0545 (16)	0.0778 (16)	0.1164 (18)	0.0085 (12)	0.0148 (14)	0.0156 (13)
C10	0.0457 (19)	0.0504 (18)	0.0618 (18)	−0.0079 (14)	0.0058 (15)	−0.0147 (16)
C16	0.0465 (19)	0.0599 (19)	0.0551 (17)	−0.0085 (15)	0.0030 (14)	0.0144 (15)
C26	0.072 (2)	0.0379 (16)	0.0467 (17)	0.0052 (15)	−0.0054 (16)	−0.0045 (14)
C18	0.051 (2)	0.0488 (19)	0.079 (2)	−0.0140 (15)	−0.0049 (17)	0.0064 (17)
C13	0.049 (2)	0.0567 (19)	0.0702 (19)	−0.0057 (16)	0.0164 (16)	0.0074 (16)
C31	0.059 (2)	0.0557 (19)	0.0471 (17)	0.0056 (15)	0.0070 (14)	0.0049 (15)
C19	0.082 (3)	0.0444 (19)	0.068 (2)	−0.0130 (17)	−0.0175 (19)	−0.0091 (16)
C30	0.053 (2)	0.0541 (19)	0.0516 (17)	0.0122 (15)	0.0069 (15)	−0.0025 (16)
C4	0.073 (3)	0.053 (2)	0.089 (2)	−0.0150 (17)	0.007 (2)	−0.0250 (19)
O5	0.144 (2)	0.0593 (15)	0.0822 (16)	0.0152 (15)	0.0077 (15)	−0.0012 (13)
C20	0.117 (3)	0.061 (2)	0.050 (2)	0.012 (2)	0.002 (2)	−0.0108 (16)
C29	0.072 (2)	0.075 (2)	0.0436 (16)	0.0157 (18)	0.0068 (15)	0.0045 (17)
C28	0.059 (2)	0.061 (2)	0.0503 (18)	0.0101 (16)	0.0105 (15)	0.0154 (16)
C5	0.094 (3)	0.042 (2)	0.111 (3)	−0.0168 (19)	0.017 (2)	−0.007 (2)
O6	0.220 (3)	0.098 (2)	0.0606 (14)	0.0392 (19)	−0.0073 (17)	−0.0251 (14)
C6	0.086 (3)	0.048 (2)	0.072 (2)	−0.0035 (17)	0.0167 (19)	0.0086 (18)
C21	0.114 (3)	0.072 (2)	0.050 (2)	0.031 (2)	0.022 (2)	0.0027 (18)

Geometric parameters (Å, º) top

O4—C27	1.380 (3)	N2—O5	1.205 (3)
O4—C17	1.398 (3)	N2—O6	1.213 (3)
O1—C11	1.375 (3)	N2—C30	1.456 (3)
O1—C1	1.396 (3)	C15—C16	1.378 (3)
N1—O3	1.218 (2)	C15—H15A	0.9300
N1—O2	1.224 (3)	C2—H2A	0.9300
N1—C14	1.463 (3)	C22—C21	1.391 (4)
C25—C23	1.408 (3)	C22—H22A	0.9300
C25—C26	1.422 (3)	C32—C31	1.382 (3)
C25—C24	1.423 (3)	C32—H32A	0.9300
C8—C1	1.365 (3)	C10—C4	1.416 (3)
C8—C9	1.434 (3)	C16—H16A	0.9300
C8—C24	1.489 (3)	C26—C19	1.405 (4)
C24—C17	1.361 (3)	C26—C20	1.408 (3)
C11—C12	1.371 (3)	C18—C19	1.349 (3)
C11—C16	1.381 (3)	C18—H18A	0.9300
C17—C18	1.389 (3)	C13—H13A	0.9300
C23—C22	1.369 (3)	C31—C30	1.368 (3)
C23—H23A	0.9300	C31—H31A	0.9300
C12—C13	1.373 (3)	C19—H19A	0.9300
C12—H12A	0.9300	C30—C29	1.364 (3)
C7—C6	1.363 (3)	C4—C5	1.347 (4)
C7—C9	1.403 (3)	C4—H4A	0.9300
C7—H7A	0.9300	C20—C21	1.350 (4)
C9—C10	1.413 (3)	C20—H20A	0.9300
C14—C15	1.363 (3)	C29—C28	1.371 (3)
C14—C13	1.374 (3)	C29—H29A	0.9300
C3—C2	1.349 (3)	C28—H28A	0.9300
C3—C10	1.405 (3)	C5—C6	1.385 (4)
C3—H3A	0.9300	C5—H5A	0.9300
C1—C2	1.396 (3)	C6—H6A	0.9300
C27—C28	1.372 (3)	C21—H21A	0.9300
C27—C32	1.377 (3)

C27—O4—C17	117.38 (19)	C1—C2—H2A	120.2
C11—O1—C1	118.0 (2)	C23—C22—C21	120.2 (3)
O3—N1—O2	123.4 (3)	C23—C22—H22A	119.9
O3—N1—C14	118.4 (3)	C21—C22—H22A	119.9
O2—N1—C14	118.2 (2)	C27—C32—C31	119.4 (2)
C23—C25—C26	118.2 (3)	C27—C32—H32A	120.3
C23—C25—C24	123.2 (2)	C31—C32—H32A	120.3
C26—C25—C24	118.7 (3)	C3—C10—C9	119.4 (2)
C1—C8—C9	117.7 (2)	C3—C10—C4	121.8 (3)
C1—C8—C24	120.6 (2)	C9—C10—C4	118.8 (3)
C9—C8—C24	121.4 (2)	C15—C16—C11	119.0 (3)
C17—C24—C25	118.3 (2)	C15—C16—H16A	120.5
C17—C24—C8	120.1 (2)	C11—C16—H16A	120.5
C25—C24—C8	121.6 (2)	C19—C26—C20	121.7 (3)
C12—C11—O1	123.6 (2)	C19—C26—C25	119.7 (3)
C12—C11—C16	120.9 (3)	C20—C26—C25	118.5 (3)
O1—C11—C16	115.4 (2)	C19—C18—C17	119.9 (3)
C24—C17—C18	123.0 (3)	C19—C18—H18A	120.1
C24—C17—O4	121.2 (2)	C17—C18—H18A	120.1
C18—C17—O4	115.8 (3)	C12—C13—C14	119.0 (3)
C22—C23—C25	121.2 (3)	C12—C13—H13A	120.5
C22—C23—H23A	119.4	C14—C13—H13A	120.5
C25—C23—H23A	119.4	C30—C31—C32	118.5 (3)
C11—C12—C13	119.9 (2)	C30—C31—H31A	120.7
C11—C12—H12A	120.1	C32—C31—H31A	120.7
C13—C12—H12A	120.1	C18—C19—C26	120.4 (3)
C6—C7—C9	121.0 (3)	C18—C19—H19A	119.8
C6—C7—H7A	119.5	C26—C19—H19A	119.8
C9—C7—H7A	119.5	C29—C30—C31	122.2 (3)
C7—C9—C10	118.2 (2)	C29—C30—N2	118.8 (3)
C7—C9—C8	122.4 (2)	C31—C30—N2	119.1 (3)
C10—C9—C8	119.3 (2)	C5—C4—C10	121.1 (3)
C15—C14—C13	121.5 (3)	C5—C4—H4A	119.5
C15—C14—N1	119.3 (3)	C10—C4—H4A	119.5
C13—C14—N1	119.2 (3)	C21—C20—C26	121.7 (3)
C2—C3—C10	121.0 (3)	C21—C20—H20A	119.1
C2—C3—H3A	119.5	C26—C20—H20A	119.1
C10—C3—H3A	119.5	C30—C29—C28	119.3 (3)
C8—C1—C2	123.0 (2)	C30—C29—H29A	120.3
C8—C1—O1	118.6 (2)	C28—C29—H29A	120.3
C2—C1—O1	118.2 (2)	C29—C28—C27	119.4 (3)
C28—C27—C32	121.0 (3)	C29—C28—H28A	120.3
C28—C27—O4	116.3 (2)	C27—C28—H28A	120.3
C32—C27—O4	122.7 (2)	C4—C5—C6	120.2 (3)
O5—N2—O6	122.5 (3)	C4—C5—H5A	119.9
O5—N2—C30	119.5 (3)	C6—C5—H5A	119.9
O6—N2—C30	118.0 (3)	C7—C6—C5	120.8 (3)
C14—C15—C16	119.7 (3)	C7—C6—H6A	119.6
C14—C15—H15A	120.2	C5—C6—H6A	119.6
C16—C15—H15A	120.2	C20—C21—C22	120.2 (3)
C3—C2—C1	119.5 (3)	C20—C21—H21A	119.9
C3—C2—H2A	120.2	C22—C21—H21A	119.9

C23—C25—C24—C17	178.9 (2)	C28—C27—C32—C31	−3.0 (4)
C26—C25—C24—C17	−0.3 (3)	O4—C27—C32—C31	179.0 (2)
C23—C25—C24—C8	−1.5 (4)	C2—C3—C10—C9	1.4 (4)
C26—C25—C24—C8	179.3 (2)	C2—C3—C10—C4	−176.9 (3)
C1—C8—C24—C17	−69.6 (3)	C7—C9—C10—C3	180.0 (2)
C9—C8—C24—C17	104.5 (3)	C8—C9—C10—C3	−2.0 (4)
C1—C8—C24—C25	110.8 (3)	C7—C9—C10—C4	−1.7 (4)
C9—C8—C24—C25	−75.1 (3)	C8—C9—C10—C4	176.3 (2)
C1—O1—C11—C12	17.3 (3)	C14—C15—C16—C11	−0.4 (4)
C1—O1—C11—C16	−165.2 (2)	C12—C11—C16—C15	0.0 (4)
C25—C24—C17—C18	−0.5 (4)	O1—C11—C16—C15	−177.5 (2)
C8—C24—C17—C18	179.9 (2)	C23—C25—C26—C19	−179.0 (2)
C25—C24—C17—O4	−177.6 (2)	C24—C25—C26—C19	0.2 (4)
C8—C24—C17—O4	2.8 (4)	C23—C25—C26—C20	1.9 (4)
C27—O4—C17—C24	−62.0 (3)	C24—C25—C26—C20	−178.9 (2)
C27—O4—C17—C18	120.7 (2)	C24—C17—C18—C19	1.4 (4)
C26—C25—C23—C22	−1.6 (4)	O4—C17—C18—C19	178.7 (2)
C24—C25—C23—C22	179.2 (2)	C11—C12—C13—C14	−0.2 (4)
O1—C11—C12—C13	177.6 (2)	C15—C14—C13—C12	−0.2 (4)
C16—C11—C12—C13	0.3 (4)	N1—C14—C13—C12	179.3 (2)
C6—C7—C9—C10	1.0 (4)	C27—C32—C31—C30	−0.2 (4)
C6—C7—C9—C8	−176.9 (2)	C17—C18—C19—C26	−1.5 (4)
C1—C8—C9—C7	179.0 (2)	C20—C26—C19—C18	179.8 (3)
C24—C8—C9—C7	4.7 (4)	C25—C26—C19—C18	0.7 (4)
C1—C8—C9—C10	1.1 (4)	C32—C31—C30—C29	3.3 (4)
C24—C8—C9—C10	−173.2 (2)	C32—C31—C30—N2	−177.7 (2)
O3—N1—C14—C15	0.9 (4)	O5—N2—C30—C29	−177.7 (3)
O2—N1—C14—C15	−179.6 (2)	O6—N2—C30—C29	2.5 (4)
O3—N1—C14—C13	−178.6 (2)	O5—N2—C30—C31	3.3 (4)
O2—N1—C14—C13	0.9 (4)	O6—N2—C30—C31	−176.5 (3)
C9—C8—C1—C2	0.5 (4)	C3—C10—C4—C5	179.6 (3)
C24—C8—C1—C2	174.8 (2)	C9—C10—C4—C5	1.3 (4)
C9—C8—C1—O1	−174.5 (2)	C19—C26—C20—C21	179.8 (3)
C24—C8—C1—O1	−0.2 (4)	C25—C26—C20—C21	−1.1 (4)
C11—O1—C1—C8	−117.7 (3)	C31—C30—C29—C28	−3.2 (4)
C11—O1—C1—C2	67.0 (3)	N2—C30—C29—C28	177.8 (3)
C17—O4—C27—C28	144.1 (2)	C30—C29—C28—C27	0.0 (4)
C17—O4—C27—C32	−37.9 (3)	C32—C27—C28—C29	3.1 (4)
C13—C14—C15—C16	0.5 (4)	O4—C27—C28—C29	−178.8 (2)
N1—C14—C15—C16	−179.0 (2)	C10—C4—C5—C6	−0.2 (5)
C10—C3—C2—C1	0.2 (4)	C9—C7—C6—C5	0.1 (4)
C8—C1—C2—C3	−1.2 (4)	C4—C5—C6—C7	−0.5 (5)
O1—C1—C2—C3	173.9 (2)	C26—C20—C21—C22	−0.1 (5)
C25—C23—C22—C21	0.5 (4)	C23—C22—C21—C20	0.4 (5)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C16—H16A···O2ⁱ	0.93	2.54	3.425 (3)	159
C32—H32A···O6ⁱⁱ	0.93	2.45	3.360 (3)	165

Symmetry codes: (i) x+1, y, z; (ii) x, −y+1/2, z+1/2.

Experimental details

Crystal data
Chemical formula	C₃₂H₂₀N₂O₆
M_r	528.50
Crystal system, space group	Monoclinic, P2₁/c
Temperature (K)	296
a, b, c (Å)	7.6159 (9), 24.810 (3), 13.5022 (15)
β (°)	95.790 (3)
V (Å³)	2538.3 (5)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.10
Crystal size (mm)	0.03 × 0.03 × 0.02

Data collection
Diffractometer	Bruker SMART APEX CCD area-detector diffractometer
Absorption correction	Multi-scan (SADABS; Bruker, 2000)
T_min, T_max	0.988, 0.990
No. of measured, independent and observed [I > 2σ(I)] reflections	13574, 4971, 2521
R_int	0.060
(sin θ/λ)_max (Å⁻¹)	0.617

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.054, 0.114, 0.86
No. of reflections	4971
No. of parameters	361
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.13, −0.21

Computer programs: SMART (Bruker, 2000), SAINT (Bruker, 2000), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), SHELXTL (Sheldrick, 2008).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C16—H16A···O2ⁱ	0.93	2.54	3.425 (3)	158.9
C32—H32A···O6ⁱⁱ	0.93	2.45	3.360 (3)	164.5

Symmetry codes: (i) x+1, y, z; (ii) x, −y+1/2, z+1/2.

Acknowledgements

This work was supported by a Start-up Grant from Southeast University to ZRQ.

References

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