Bis[4-(3-amino­phen­oxy)phen­yl] ketone

Wang, Y.; Zhu, X.; Ma, X.; Gao, G.; Men, J.

doi:10.1107/S1600536809025951

organic compounds

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ISSN: 2056-9890

Volume 65| Part 8| August 2009| Page o1823

doi:10.1107/S1600536809025951

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Bis[4-(3-aminophenoxy)phenyl] ketone

Yang Wang,^a Xin-yi Zhu,^a Xiao-yan Ma,^b Guo-wei Gao ^a and Jian Men ^a ^*

^aCollege of Chemistry, Sichuan University, Chengdu 610064, People's Republic of China, and ^bCollege of Materials and Chemical Engineering, Chengdu University of Technology, Chengdu 610059, People's Republic of China
^*Correspondence e-mail: menjian@scu.edu.cn

(Received 27 June 2009; accepted 4 July 2009; online 11 July 2009)

In the molecule of the title compound, C₂₅H₂₀N₂O₃, the dihedral angles formed by adjacent benzene rings are 66.75 (8), 48.37 (8) and 71.43 (9)°. In the crystal structure, centrosymmetrically related molecules are linked into dimers by intermolecular N—H⋯O hydrogen bonds.

Related literature

For the properties and synthesis of the title compound, see: Wilson et al. (1990 ); Mehdipour-Ataei & Saidi (2008 ). For the applications of the title compound, see: Rao & Prabhakaran (1992 ).

Experimental

Crystal data

C₂₅H₂₀N₂O₃
M_r = 396.43
Triclinic, $[P \overline 1]$
a = 7.370 (3) Å
b = 11.856 (3) Å
c = 12.319 (3) Å
α = 101.79 (4)°
β = 95.10 (4)°
γ = 107.86 (3)°
V = 989.6 (6) Å³
Z = 2
Mo Kα radiation
μ = 0.09 mm⁻¹
T = 292 K
0.48 × 0.42 × 0.23 mm

Data collection

Enraf–Nonius CAD-4 diffractometer
Absorption correction: none
3693 measured reflections
3682 independent reflections
2206 reflections with I > 2σ(I)
R_int = 0.006
3 standard reflections every 200 reflections intensity decay: 1.5%

Refinement

R[F² > 2σ(F²)] = 0.053
wR(F²) = 0.165
S = 1.05
3682 reflections
288 parameters
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.23 e Å⁻³
Δρ_min = −0.24 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1N1⋯O1ⁱ	0.92 (4)	2.32 (4)	3.223 (5)	164 (3)
Symmetry code: (i) -x+2, -y+2, -z+1.

Data collection: DIFRAC (Gabe & White, 1993 ); cell refinement: DIFRAC; data reduction: NRCVAX (Gabe et al., 1989 ); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997 ); software used to prepare material for publication: SHELXL97.

Supporting information

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536809025951/rz2344sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536809025951/rz2344Isup2.hkl

checkCIF report

Comment top

Aromatic polyimides has found useful applications in aircraft technology, space vehicles, sea transport equipment and other applications due to their excellent thermal stability, good mechanical properties, low dielectric constants and intrinsic purity (Wilson et al., 1990). The title compound is an important raw material for the synthesis of aromatic polyimides, as the presence of ether and ketone groups connected by aromatic rings greatly improves the chain flexibility (Rao & Prabhakaran, 1992; Mehdipour-Ataei & Saidi, 2008). Herein, we report the synthesis and crystal structure of the title compound.

The structure of the title compound (Fig. 1) is not planar. The dihedral angle between the two central benzene rings, ring A (C7–C12) and ring B (C14–C19), is 48.37 (8)°. Ring A forms a dihedral angle of 66.75 (8)° with the C1–C6 benzene ring. The corresponding dihedral angle between ring B and the C20–C25 benzene ring is 71.43 (9)°. The plane formed by atoms C10, C14, O1 and C13, makes a dihedral angle of 22.28 (12)° and 31.23 (8)° with ring A and B, respectively. The crystal structure is stabilized by N—H···O hydrogen bonds (Table 1) linking centrosymmetrically related molecules into dimers.

Related literature top

For the properties and synthesis of the title compound, see: Wilson et al., (1990); Mehdipour-Ataei & Saidi (2008). For the applications of the title compound, see: Rao & Prabhakaran (1992). [Author: please revise scheme to show 3-amino rather than 4-amino]

Experimental top

4,4'-Difluorobenzophenone (11.0 g, 0.05 mol), m-aminophenol (22.0 g, 0.20 mol) and anhydrous potassium carbonate (14.0 g, 0.10 mol) were dissolved in a solution of toluene (60 ml) and N,N-dimethylformamide (100 ml) in a three-necked flask. The mixture was heated to reflux and water was removed by azeotropic distillation. After complete dehydration, the mixture was poured to a large excess of ice water. Then, the precipitated solid was collected by filtration and recrystallized from ethanol to obtain a tan solid (16.5 g, 76% yield, m.p.411–413 K). Red single crystals suitable for X-ray diffraction were obtained by slow evaporation at room temperature of a toluene solution.

Computing details top

Data collection: DIFRAC (Gabe & White, 1993); cell refinement: DIFRAC (Gabe & White, 1993); data reduction: NRCVAX (Gabe et al., 1989); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997); software used to prepare material for publication: SHELXL97 (Sheldrick, 2008).

Figures top

Fig. 1. The molecular structure of the title compound, with displacement ellipsoids drawn at the 30% probability level.

Bis[4-(3-aminophenoxy)phenyl] ketone top

Crystal data top

C₂₅H₂₀N₂O₃	Z = 2
M_r = 396.43	F(000) = 416
Triclinic, P1	D_x = 1.330 Mg m⁻³
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 7.370 (3) Å	Cell parameters from 23 reflections
b = 11.856 (3) Å	θ = 5.4–5.6°
c = 12.319 (3) Å	µ = 0.09 mm⁻¹
α = 101.79 (4)°	T = 292 K
β = 95.10 (4)°	Block, red
γ = 107.86 (3)°	0.48 × 0.42 × 0.23 mm
V = 989.6 (6) Å³

Data collection top

Enraf–Nonius CAD-4 diffractometer	R_int = 0.006
Radiation source: fine-focus sealed tube	θ_max = 25.5°, θ_min = 1.7°
Graphite monochromator	h = −8→8
ω/2θ scans	k = −4→14
3693 measured reflections	l = −14→14
3682 independent reflections	3 standard reflections every 200 reflections
2206 reflections with I > 2σ(I)	intensity decay: 1.5%

Refinement top

Refinement on F²	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: mixed
R[F² > 2σ(F²)] = 0.053	H atoms treated by a mixture of independent and constrained refinement
wR(F²) = 0.165	w = 1/[σ²(F_o²) + (0.0943P)²] where P = (F_o² + 2F_c²)/3
S = 1.05	(Δ/σ)_max < 0.001
3682 reflections	Δρ_max = 0.23 e Å⁻³
288 parameters	Δρ_min = −0.24 e Å⁻³
0 restraints	Extinction correction: SHELXL97 (Sheldrick, 2008), Fc^*=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.027 (5)

Crystal data top

C₂₅H₂₀N₂O₃	γ = 107.86 (3)°
M_r = 396.43	V = 989.6 (6) Å³
Triclinic, P1	Z = 2
a = 7.370 (3) Å	Mo Kα radiation
b = 11.856 (3) Å	µ = 0.09 mm⁻¹
c = 12.319 (3) Å	T = 292 K
α = 101.79 (4)°	0.48 × 0.42 × 0.23 mm
β = 95.10 (4)°

Data collection top

Enraf–Nonius CAD-4 diffractometer	R_int = 0.006
3693 measured reflections	3 standard reflections every 200 reflections
3682 independent reflections	intensity decay: 1.5%
2206 reflections with I > 2σ(I)

Refinement top

R[F² > 2σ(F²)] = 0.053	0 restraints
wR(F²) = 0.165	H atoms treated by a mixture of independent and constrained refinement
S = 1.05	Δρ_max = 0.23 e Å⁻³
3682 reflections	Δρ_min = −0.24 e Å⁻³
288 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
O1	0.4068 (2)	0.59493 (16)	0.42259 (15)	0.0665 (5)
O2	1.2554 (2)	0.95837 (18)	0.55618 (15)	0.0746 (6)
O3	0.0557 (2)	0.57862 (15)	0.86702 (15)	0.0623 (5)
N1	1.7663 (5)	1.3024 (3)	0.7708 (4)	0.0988 (11)
H1N1	1.729 (5)	1.346 (3)	0.725 (3)	0.116 (15)*
H2N1	1.840 (5)	1.333 (3)	0.828 (3)	0.109 (15)*
N2	−0.3694 (6)	0.6550 (4)	1.1145 (3)	0.1179 (13)
H1N2	−0.378 (6)	0.581 (4)	1.131 (3)	0.119 (14)*
H2N2	−0.399 (8)	0.712 (5)	1.153 (5)	0.19 (3)*
C1	1.6441 (3)	1.1849 (2)	0.7619 (2)	0.0591 (7)
C2	1.6600 (4)	1.1216 (3)	0.8431 (2)	0.0655 (7)
H2	1.7550	1.1581	0.9064	0.079*
C3	1.5354 (4)	1.0050 (3)	0.8303 (2)	0.0631 (7)
H3	1.5464	0.9638	0.8859	0.076*
C4	1.3949 (3)	0.9477 (2)	0.7371 (2)	0.0544 (6)
H4	1.3115	0.8685	0.7286	0.065*
C5	1.3819 (3)	1.0112 (2)	0.6574 (2)	0.0509 (6)
C6	1.5030 (3)	1.1280 (2)	0.6682 (2)	0.0558 (7)
H6	1.4901	1.1689	0.6126	0.067*
C7	1.0692 (3)	0.8848 (2)	0.5542 (2)	0.0518 (6)
C8	0.9903 (3)	0.7910 (2)	0.4600 (2)	0.0549 (6)
H8	1.0622	0.7789	0.4031	0.066*
C9	0.8035 (3)	0.7150 (2)	0.4507 (2)	0.0517 (6)
H9	0.7494	0.6512	0.3869	0.062*
C10	0.6938 (3)	0.73176 (19)	0.53531 (19)	0.0450 (6)
C11	0.7750 (3)	0.8300 (2)	0.6275 (2)	0.0511 (6)
H11	0.7023	0.8444	0.6834	0.061*
C12	0.9628 (3)	0.9070 (2)	0.6377 (2)	0.0543 (6)
H12	1.0165	0.9728	0.7000	0.065*
C13	0.4904 (3)	0.6501 (2)	0.5182 (2)	0.0505 (6)
C14	0.3844 (3)	0.63592 (19)	0.6137 (2)	0.0451 (6)
C15	0.1849 (3)	0.61103 (19)	0.5934 (2)	0.0475 (6)
H15	0.1256	0.6057	0.5218	0.057*
C16	0.0742 (3)	0.5943 (2)	0.6765 (2)	0.0521 (6)
H16	−0.0585	0.5779	0.6615	0.063*
C17	0.1629 (3)	0.6021 (2)	0.7822 (2)	0.0502 (6)
C18	0.3584 (3)	0.6242 (2)	0.8042 (2)	0.0552 (6)
H18	0.4165	0.6282	0.8757	0.066*
C19	0.4680 (3)	0.6404 (2)	0.7205 (2)	0.0539 (6)
H19	0.6000	0.6546	0.7356	0.065*
C20	−0.0391 (3)	0.6582 (2)	0.9107 (2)	0.0470 (6)
C21	−0.1542 (3)	0.6200 (2)	0.9866 (2)	0.0560 (6)
H21	−0.1692	0.5443	1.0020	0.067*
C22	−0.2484 (4)	0.6946 (3)	1.0405 (2)	0.0665 (7)
C23	−0.2239 (4)	0.8067 (3)	1.0155 (3)	0.0705 (8)
H23	−0.2847	0.8584	1.0514	0.085*
C24	−0.1107 (4)	0.8412 (2)	0.9382 (2)	0.0635 (7)
H24	−0.0982	0.9157	0.9210	0.076*
C25	−0.0142 (3)	0.7687 (2)	0.8849 (2)	0.0550 (6)
H25	0.0647	0.7937	0.8334	0.066*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
O1	0.0462 (10)	0.0733 (12)	0.0579 (12)	0.0017 (9)	−0.0019 (9)	0.0004 (9)
O2	0.0424 (10)	0.1008 (14)	0.0539 (12)	−0.0116 (9)	0.0015 (8)	0.0184 (10)
O3	0.0645 (11)	0.0627 (10)	0.0744 (13)	0.0286 (9)	0.0262 (10)	0.0307 (9)
N1	0.088 (2)	0.0664 (18)	0.105 (3)	−0.0097 (16)	−0.007 (2)	0.0029 (18)
N2	0.136 (3)	0.121 (3)	0.142 (3)	0.069 (3)	0.092 (3)	0.059 (3)
C1	0.0427 (13)	0.0545 (15)	0.0680 (18)	0.0079 (12)	0.0060 (13)	0.0026 (13)
C2	0.0490 (15)	0.0799 (19)	0.0562 (17)	0.0168 (14)	−0.0056 (13)	0.0050 (14)
C3	0.0568 (16)	0.0775 (18)	0.0614 (18)	0.0285 (14)	0.0051 (14)	0.0232 (15)
C4	0.0461 (13)	0.0527 (14)	0.0602 (16)	0.0117 (11)	0.0058 (12)	0.0129 (12)
C5	0.0317 (11)	0.0637 (15)	0.0497 (15)	0.0084 (11)	0.0058 (11)	0.0092 (12)
C6	0.0421 (13)	0.0581 (15)	0.0662 (17)	0.0109 (12)	0.0091 (12)	0.0217 (13)
C7	0.0373 (12)	0.0609 (15)	0.0496 (15)	0.0040 (11)	0.0012 (11)	0.0184 (12)
C8	0.0405 (13)	0.0699 (16)	0.0527 (16)	0.0158 (12)	0.0086 (11)	0.0151 (13)
C9	0.0449 (13)	0.0532 (14)	0.0467 (15)	0.0110 (11)	−0.0030 (11)	0.0025 (11)
C10	0.0368 (12)	0.0481 (13)	0.0460 (14)	0.0111 (10)	−0.0010 (10)	0.0101 (11)
C11	0.0395 (13)	0.0554 (14)	0.0544 (16)	0.0122 (11)	0.0072 (11)	0.0107 (12)
C12	0.0446 (14)	0.0606 (15)	0.0450 (14)	0.0052 (11)	−0.0002 (11)	0.0075 (11)
C13	0.0394 (13)	0.0462 (13)	0.0580 (17)	0.0100 (11)	−0.0019 (12)	0.0062 (12)
C14	0.0324 (11)	0.0424 (12)	0.0548 (15)	0.0075 (9)	−0.0002 (10)	0.0100 (11)
C15	0.0379 (12)	0.0471 (13)	0.0491 (14)	0.0094 (10)	−0.0064 (11)	0.0066 (11)
C16	0.0331 (12)	0.0540 (14)	0.0647 (17)	0.0119 (10)	0.0018 (12)	0.0109 (12)
C17	0.0476 (14)	0.0433 (12)	0.0589 (16)	0.0128 (10)	0.0094 (12)	0.0140 (11)
C18	0.0460 (14)	0.0611 (15)	0.0527 (16)	0.0105 (11)	−0.0043 (12)	0.0176 (12)
C19	0.0336 (12)	0.0553 (14)	0.0661 (17)	0.0072 (10)	−0.0026 (12)	0.0167 (12)
C20	0.0384 (12)	0.0478 (13)	0.0482 (14)	0.0095 (10)	−0.0022 (11)	0.0089 (11)
C21	0.0472 (13)	0.0560 (15)	0.0651 (17)	0.0156 (12)	0.0063 (12)	0.0189 (13)
C22	0.0605 (17)	0.0778 (19)	0.0654 (19)	0.0269 (15)	0.0164 (14)	0.0179 (15)
C23	0.0716 (19)	0.0689 (18)	0.072 (2)	0.0342 (15)	0.0058 (16)	0.0045 (15)
C24	0.0725 (18)	0.0523 (15)	0.0602 (18)	0.0216 (14)	−0.0049 (14)	0.0076 (13)
C25	0.0520 (14)	0.0529 (14)	0.0546 (16)	0.0118 (12)	0.0022 (12)	0.0128 (12)

Geometric parameters (Å, º) top

O1—C13	1.226 (3)	C10—C11	1.384 (3)
O2—C7	1.377 (3)	C10—C13	1.484 (3)
O2—C5	1.390 (3)	C11—C12	1.383 (3)
O3—C17	1.387 (3)	C11—H11	0.9300
O3—C20	1.390 (3)	C12—H12	0.9300
N1—C1	1.384 (4)	C13—C14	1.478 (3)
N1—H1N1	0.92 (4)	C14—C19	1.386 (3)
N1—H2N1	0.79 (4)	C14—C15	1.396 (3)
N2—C22	1.383 (4)	C15—C16	1.373 (3)
N2—H1N2	0.93 (4)	C15—H15	0.9300
N2—H2N2	0.84 (5)	C16—C17	1.377 (3)
C1—C6	1.381 (4)	C16—H16	0.9300
C1—C2	1.384 (4)	C17—C18	1.374 (3)
C2—C3	1.373 (4)	C18—C19	1.374 (3)
C2—H2	0.9300	C18—H18	0.9300
C3—C4	1.375 (4)	C19—H19	0.9300
C3—H3	0.9300	C20—C21	1.370 (3)
C4—C5	1.368 (3)	C20—C25	1.373 (3)
C4—H4	0.9300	C21—C22	1.387 (4)
C5—C6	1.370 (3)	C21—H21	0.9300
C6—H6	0.9300	C22—C23	1.387 (4)
C7—C8	1.371 (3)	C23—C24	1.364 (4)
C7—C12	1.379 (3)	C23—H23	0.9300
C8—C9	1.374 (3)	C24—C25	1.380 (4)
C8—H8	0.9300	C24—H24	0.9300
C9—C10	1.394 (3)	C25—H25	0.9300
C9—H9	0.9300

C7—O2—C5	120.22 (19)	C7—C12—H12	120.5
C17—O3—C20	119.63 (18)	C11—C12—H12	120.5
C1—N1—H1N1	117 (2)	O1—C13—C14	119.2 (2)
C1—N1—H2N1	115 (3)	O1—C13—C10	119.3 (2)
H1N1—N1—H2N1	124 (4)	C14—C13—C10	121.5 (2)
C22—N2—H1N2	118 (2)	C19—C14—C15	117.8 (2)
C22—N2—H2N2	112 (4)	C19—C14—C13	124.5 (2)
H1N2—N2—H2N2	127 (5)	C15—C14—C13	117.6 (2)
C6—C1—N1	119.0 (3)	C16—C15—C14	121.7 (2)
C6—C1—C2	118.8 (2)	C16—C15—H15	119.2
N1—C1—C2	122.2 (3)	C14—C15—H15	119.2
C3—C2—C1	120.1 (3)	C15—C16—C17	118.9 (2)
C3—C2—H2	120.0	C15—C16—H16	120.6
C1—C2—H2	120.0	C17—C16—H16	120.6
C2—C3—C4	121.5 (3)	C18—C17—C16	120.8 (2)
C2—C3—H3	119.2	C18—C17—O3	118.1 (2)
C4—C3—H3	119.2	C16—C17—O3	121.0 (2)
C5—C4—C3	117.7 (2)	C19—C18—C17	119.9 (2)
C5—C4—H4	121.2	C19—C18—H18	120.0
C3—C4—H4	121.2	C17—C18—H18	120.0
C4—C5—C6	122.2 (2)	C18—C19—C14	120.9 (2)
C4—C5—O2	122.2 (2)	C18—C19—H19	119.6
C6—C5—O2	115.4 (2)	C14—C19—H19	119.6
C5—C6—C1	119.8 (2)	C21—C20—C25	122.1 (2)
C5—C6—H6	120.1	C21—C20—O3	114.4 (2)
C1—C6—H6	120.1	C25—C20—O3	123.5 (2)
C8—C7—O2	115.7 (2)	C20—C21—C22	119.7 (2)
C8—C7—C12	121.3 (2)	C20—C21—H21	120.1
O2—C7—C12	122.9 (2)	C22—C21—H21	120.1
C7—C8—C9	119.2 (2)	N2—C22—C21	120.0 (3)
C7—C8—H8	120.4	N2—C22—C23	121.2 (3)
C9—C8—H8	120.4	C21—C22—C23	118.8 (3)
C8—C9—C10	121.1 (2)	C24—C23—C22	120.0 (3)
C8—C9—H9	119.4	C24—C23—H23	120.0
C10—C9—H9	119.4	C22—C23—H23	120.0
C11—C10—C9	118.4 (2)	C23—C24—C25	121.9 (2)
C11—C10—C13	122.8 (2)	C23—C24—H24	119.0
C9—C10—C13	118.6 (2)	C25—C24—H24	119.0
C12—C11—C10	120.9 (2)	C20—C25—C24	117.4 (2)
C12—C11—H11	119.5	C20—C25—H25	121.3
C10—C11—H11	119.5	C24—C25—H25	121.3
C7—C12—C11	119.0 (2)

C6—C1—C2—C3	−0.7 (4)	O1—C13—C14—C19	147.9 (2)
N1—C1—C2—C3	−179.9 (3)	C10—C13—C14—C19	−33.6 (3)
C1—C2—C3—C4	0.9 (4)	O1—C13—C14—C15	−29.1 (3)
C2—C3—C4—C5	−0.5 (4)	C10—C13—C14—C15	149.3 (2)
C3—C4—C5—C6	−0.1 (4)	C19—C14—C15—C16	1.5 (3)
C3—C4—C5—O2	174.8 (2)	C13—C14—C15—C16	178.8 (2)
C7—O2—C5—C4	43.0 (3)	C14—C15—C16—C17	−0.1 (3)
C7—O2—C5—C6	−141.8 (2)	C15—C16—C17—C18	−1.1 (3)
C4—C5—C6—C1	0.2 (4)	C15—C16—C17—O3	−176.1 (2)
O2—C5—C6—C1	−174.9 (2)	C20—O3—C17—C18	116.9 (2)
N1—C1—C6—C5	179.4 (3)	C20—O3—C17—C16	−68.0 (3)
C2—C1—C6—C5	0.1 (4)	C16—C17—C18—C19	0.9 (4)
C5—O2—C7—C8	−147.3 (2)	O3—C17—C18—C19	176.0 (2)
C5—O2—C7—C12	36.4 (4)	C17—C18—C19—C14	0.6 (4)
O2—C7—C8—C9	−178.7 (2)	C15—C14—C19—C18	−1.8 (3)
C12—C7—C8—C9	−2.4 (4)	C13—C14—C19—C18	−178.8 (2)
C7—C8—C9—C10	0.0 (4)	C17—O3—C20—C21	174.4 (2)
C8—C9—C10—C11	2.4 (3)	C17—O3—C20—C25	−8.5 (3)
C8—C9—C10—C13	177.4 (2)	C25—C20—C21—C22	−0.5 (4)
C9—C10—C11—C12	−2.4 (3)	O3—C20—C21—C22	176.6 (2)
C13—C10—C11—C12	−177.1 (2)	C20—C21—C22—N2	178.0 (3)
C8—C7—C12—C11	2.4 (4)	C20—C21—C22—C23	0.3 (4)
O2—C7—C12—C11	178.4 (2)	N2—C22—C23—C24	−177.0 (3)
C10—C11—C12—C7	0.1 (4)	C21—C22—C23—C24	0.8 (4)
C11—C10—C13—O1	154.3 (2)	C22—C23—C24—C25	−1.6 (4)
C9—C10—C13—O1	−20.4 (3)	C21—C20—C25—C24	−0.2 (4)
C11—C10—C13—C14	−24.2 (3)	O3—C20—C25—C24	−177.1 (2)
C9—C10—C13—C14	161.1 (2)	C23—C24—C25—C20	1.3 (4)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1N1···O1ⁱ	0.92 (4)	2.32 (4)	3.223 (5)	164 (3)

Symmetry code: (i) −x+2, −y+2, −z+1.

Experimental details

Crystal data
Chemical formula	C₂₅H₂₀N₂O₃
M_r	396.43
Crystal system, space group	Triclinic, P1
Temperature (K)	292
a, b, c (Å)	7.370 (3), 11.856 (3), 12.319 (3)
α, β, γ (°)	101.79 (4), 95.10 (4), 107.86 (3)
V (Å³)	989.6 (6)
Z	2
Radiation type	Mo Kα
µ (mm⁻¹)	0.09
Crystal size (mm)	0.48 × 0.42 × 0.23

Data collection
Diffractometer	Enraf–Nonius CAD-4 diffractometer
Absorption correction	–
No. of measured, independent and observed [I > 2σ(I)] reflections	3693, 3682, 2206
R_int	0.006
(sin θ/λ)_max (Å⁻¹)	0.606

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.053, 0.165, 1.05
No. of reflections	3682
No. of parameters	288
H-atom treatment	H atoms treated by a mixture of independent and constrained refinement
Δρ_max, Δρ_min (e Å⁻³)	0.23, −0.24

Computer programs: DIFRAC (Gabe & White, 1993), NRCVAX (Gabe et al., 1989), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), ORTEP-3 for Windows (Farrugia, 1997).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1N1···O1ⁱ	0.92 (4)	2.32 (4)	3.223 (5)	164 (3)

Symmetry code: (i) −x+2, −y+2, −z+1.

Acknowledgements

The authors are grateful to the Undergraduates' Innovative Experiment Project of Sichuan University and thank Mr Zhi-Hua Mao of Sichuan University for the X-Ray data collection.

References

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