(2R)-N-(2-Benzoyl­phen­yl)-1-benzyl­pyrrolidine-2-carboxamide

Nayab, S.; Lee, H.-I.; Jeong, J.H.

doi:10.1107/S1600536811033836

organic compounds

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ISSN: 2056-9890

Volume 67| Part 9| September 2011| Page o2478

doi:10.1107/S1600536811033836

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(2R)-N-(2-Benzoylphenyl)-1-benzylpyrrolidine-2-carboxamide

Saira Nayab,^a Hong-In Lee ^a and Jong Hwa Jeong ^a ^*

^aDepartment of Chemistry, Kyungpook National University, Taegu, 702-701, Republic of Korea
^*Correspondence e-mail: jeongjh@knu.ac.kr

(Received 12 July 2011; accepted 19 August 2011; online 27 August 2011)

In the title compound, C₂₅H₂₄N₂O₂, the dihedral angle between the two benzene rings of the benzophenone moiety is 59.10 (6)°. An intramolecular, bifurcated N—H⋯(O,N) hydrogen bond, which generates S(6) and S(5) rings, respectively, helps to establish the overall conformation of the molecule.

Related literature

For applications of the title compound, see: Deng et al. (2008 ); Purser et al. (2008 ). For further synthetic details, see: Tararov et al. (1997 ); Wang et al. (2011 ).

Experimental

Crystal data

C₂₅H₂₄N₂O₂
M_r = 384.46
Orthorhombic, P 2₁ 2₁ 2₁
a = 8.4036 (7) Å
b = 11.2215 (8) Å
c = 21.4182 (12) Å
V = 2019.8 (2) Å³
Z = 4
Mo Kα radiation
μ = 0.08 mm⁻¹
T = 293 K
0.45 × 0.40 × 0.35 mm

Data collection

Enraf–Nonius CAD-4 four-circle diffractometer
4479 measured reflections
3740 independent reflections
2372 reflections with I > 2σ(I)
R_int = 0.013
3 standard reflections every 60 min intensity decay: < 0.2%

Refinement

R[F² > 2σ(F²)] = 0.034
wR(F²) = 0.084
S = 0.93
3740 reflections
266 parameters
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.12 e Å⁻³
Δρ_min = −0.12 e Å⁻³
Absolute structure: Flack (1983 ), 1587 Friedel pairs
Flack parameter: −0.2 (15)

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N2—H2N⋯O2	0.855 (19)	2.246 (17)	2.810 (2)	123.5 (15)
N2—H2N⋯N1	0.855 (19)	2.209 (18)	2.663 (2)	113.1 (14)

Data collection: CAD-4 Software (Enraf–Nonius, 1989 ); cell refinement: CAD-4 Software; data reduction: XCAD (McArdle, 1999 ); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEPIII (Burnett & Johnson, 1996 ); software used to prepare material for publication: SHELXL97.

Supporting information

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536811033836/hb5950sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536811033836/hb5950Isup2.hkl

Supporting information file. DOI: 10.1107/S1600536811033836/hb5950Isup3.cml

checkCIF report

Comment top

Asymmetric synthesis of non-proteinogenic amino acids based on the use of chiral auxiliaries has creative potentials in medicinal chemistry (Purser et al., 2008). Among the non-proteinogenic amino acids, 2-[(N- benzylpyrrolyl)amino]benzophenone, which can be both simply and stereo- selectively synthesized with low cost, is readily available for the studies of systematic medicinal chemistry (Deng et al., 2008). In this study, we report the crystal structure of the title compound, (I).

Two phenyl groups of benzophenone fragment are rotated from the carbonyl plane due to the steric hindrance caused by the phenyl moiety of the benzyl group. The configuration of C at the pyrrolydine fragment is R. There are two intramolecular N-H···O and N-H···N hydrogen bonds forming six and five membered rings, respectively.

Related literature top

For applications of the title compound, see: Deng et al. (2008); Purser et al. (2008). For further synthetic details, see: Tararov et al. (1997); Wang et al. (2011).

Experimental top

The title compound was synthesized by the reported method (Tararov et al., 1997; Wang et al., 2011). Colourless blocks of (I) were obtained through slow diffusion of hexane in to CH₂Cl₂ solution at room temperature.

Computing details top

Data collection: CAD-4 Software (Enraf–Nonius, 1989); cell refinement: CAD-4 Software (Enraf–Nonius, 1989); data reduction: XCAD (McArdle, 1999); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEPIII (Burnett & Johnson, 1996); software used to prepare material for publication: SHELXL97 (Sheldrick, 2008).

Figures top

Fig. 1. The molecular structure of (I) with displacement ellipsoids drawn at the 40% probability level. Hydrgen bonds are indicated by dashed lines.

(2R)-N-(2-Benzoylphenyl)-1-benzylpyrrolidine-2-carboxamide top

Crystal data top

C₂₅H₂₄N₂O₂	F(000) = 816
M_r = 384.46	D_x = 1.264 Mg m⁻³
Orthorhombic, P2₁2₁2₁	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2ac 2ab	Cell parameters from 3 reflections
a = 8.4036 (7) Å	θ = 9.3–11.9°
b = 11.2215 (8) Å	µ = 0.08 mm⁻¹
c = 21.4182 (12) Å	T = 293 K
V = 2019.8 (2) Å³	Block, colorless
Z = 4	0.45 × 0.40 × 0.35 mm

Data collection top

Enraf–Nonius CAD-4 four-circle diffractometer	R_int = 0.013
Radiation source: fine-focus sealed tube	θ_max = 25.5°, θ_min = 1.9°
Graphite monochromator	h = −10→10
ω/2θ scans	k = −13→13
4479 measured reflections	l = −25→25
3740 independent reflections	3 standard reflections every 60 min
2372 reflections with I > 2σ(I)	intensity decay: < 0.2%

Refinement top

Refinement on F²	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F² > 2σ(F²)] = 0.034	H atoms treated by a mixture of independent and constrained refinement
wR(F²) = 0.084	w = 1/[σ²(F_o²) + (0.0442P)²] where P = (F_o² + 2F_c²)/3
S = 0.93	(Δ/σ)_max = 0.001
3740 reflections	Δρ_max = 0.12 e Å⁻³
266 parameters	Δρ_min = −0.12 e Å⁻³
0 restraints	Absolute structure: Flack (1983), 1587 Friedel pairs
Primary atom site location: structure-invariant direct methods	Absolute structure parameter: −0.2 (15)

Crystal data top

C₂₅H₂₄N₂O₂	V = 2019.8 (2) Å³
M_r = 384.46	Z = 4
Orthorhombic, P2₁2₁2₁	Mo Kα radiation
a = 8.4036 (7) Å	µ = 0.08 mm⁻¹
b = 11.2215 (8) Å	T = 293 K
c = 21.4182 (12) Å	0.45 × 0.40 × 0.35 mm

Data collection top

Enraf–Nonius CAD-4 four-circle diffractometer	R_int = 0.013
4479 measured reflections	3 standard reflections every 60 min
3740 independent reflections	intensity decay: < 0.2%
2372 reflections with I > 2σ(I)

Refinement top

R[F² > 2σ(F²)] = 0.034	H atoms treated by a mixture of independent and constrained refinement
wR(F²) = 0.084	Δρ_max = 0.12 e Å⁻³
S = 0.93	Δρ_min = −0.12 e Å⁻³
3740 reflections	Absolute structure: Flack (1983), 1587 Friedel pairs
266 parameters	Absolute structure parameter: −0.2 (15)
0 restraints

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

	x	y	z	U_iso*/U_eq
N1	0.61424 (19)	0.35261 (13)	0.85208 (7)	0.0448 (4)
O1	0.6320 (2)	0.53634 (14)	0.71393 (7)	0.0686 (5)
O2	1.0339 (2)	0.48686 (13)	0.88092 (7)	0.0774 (5)
N2	0.7694 (2)	0.53942 (15)	0.80552 (8)	0.0444 (4)
H2N	0.792 (2)	0.4945 (17)	0.8365 (9)	0.047 (6)*
C1	0.6389 (3)	0.22394 (17)	0.85790 (9)	0.0573 (6)
H1A	0.5382	0.1818	0.8598	0.069*
H1B	0.7010	0.2050	0.8947	0.069*
C2	0.7280 (3)	0.1939 (2)	0.79945 (11)	0.0724 (7)
H2A	0.7201	0.1096	0.7900	0.087*
H2B	0.8394	0.2156	0.8031	0.087*
C3	0.6456 (3)	0.26809 (19)	0.75016 (10)	0.0612 (6)
H3A	0.5577	0.2245	0.7316	0.073*
H3B	0.7193	0.2910	0.7175	0.073*
C4	0.5852 (2)	0.37804 (17)	0.78583 (8)	0.0465 (5)
H4	0.4702	0.3850	0.7793	0.056*
C5	0.6641 (2)	0.49309 (17)	0.76437 (9)	0.0450 (5)
C6	0.8458 (2)	0.65120 (16)	0.80547 (8)	0.0382 (4)
C7	0.8141 (2)	0.73603 (17)	0.76016 (9)	0.0444 (5)
H7	0.7474	0.7173	0.7269	0.053*
C8	0.8807 (3)	0.84794 (18)	0.76397 (9)	0.0524 (5)
H8	0.8594	0.9036	0.7329	0.063*
C9	0.9778 (3)	0.87866 (17)	0.81265 (10)	0.0542 (5)
H9	1.0199	0.9551	0.8153	0.065*
C10	1.0125 (2)	0.79505 (16)	0.85766 (9)	0.0482 (5)
H10	1.0787	0.8158	0.8907	0.058*
C11	0.9504 (2)	0.67965 (16)	0.85471 (8)	0.0393 (4)
C12	1.0078 (2)	0.58769 (18)	0.89961 (9)	0.0468 (5)
C13	1.0368 (2)	0.61718 (16)	0.96635 (8)	0.0425 (5)
C14	0.9582 (3)	0.70905 (17)	0.99693 (9)	0.0518 (5)
H14	0.8901	0.7590	0.9749	0.062*
C15	0.9812 (3)	0.7261 (2)	1.06040 (9)	0.0650 (6)
H15	0.9274	0.7868	1.0811	0.078*
C16	1.0839 (3)	0.6531 (2)	1.09295 (10)	0.0688 (7)
H16	1.0993	0.6648	1.1355	0.083*
C17	1.1639 (3)	0.5627 (2)	1.06260 (10)	0.0659 (7)
H17	1.2347	0.5146	1.0845	0.079*
C18	1.1388 (3)	0.54412 (18)	1.00017 (9)	0.0537 (5)
H18	1.1908	0.4817	0.9801	0.064*
C19	0.4917 (3)	0.40031 (19)	0.89345 (9)	0.0555 (6)
H19A	0.3930	0.3574	0.8866	0.067*
H19B	0.4734	0.4835	0.8834	0.067*
C20	0.5386 (2)	0.38994 (17)	0.96107 (9)	0.0462 (5)
C21	0.6451 (3)	0.46882 (17)	0.98709 (10)	0.0539 (5)
H21	0.6849	0.5305	0.9627	0.065*
C22	0.6942 (3)	0.4592 (2)	1.04770 (10)	0.0637 (6)
H22	0.7675	0.5130	1.0639	0.076*
C23	0.6350 (3)	0.3700 (2)	1.08441 (10)	0.0662 (7)
H23	0.6667	0.3635	1.1259	0.079*
C24	0.5285 (3)	0.2902 (2)	1.05976 (10)	0.0670 (7)
H24	0.4892	0.2286	1.0844	0.080*
C25	0.4798 (3)	0.30099 (18)	0.99869 (10)	0.0596 (6)
H25	0.4061	0.2473	0.9826	0.071*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
N1	0.0480 (9)	0.0427 (9)	0.0435 (8)	0.0001 (8)	0.0027 (8)	0.0000 (7)
O1	0.0901 (12)	0.0611 (9)	0.0546 (9)	−0.0080 (9)	−0.0274 (8)	0.0103 (7)
O2	0.1167 (15)	0.0469 (9)	0.0685 (10)	0.0280 (9)	−0.0326 (10)	−0.0149 (8)
N2	0.0541 (11)	0.0401 (9)	0.0391 (9)	−0.0043 (9)	−0.0060 (8)	0.0050 (8)
C1	0.0671 (15)	0.0447 (12)	0.0601 (13)	−0.0006 (11)	−0.0044 (12)	0.0001 (11)
C2	0.0741 (17)	0.0630 (15)	0.0802 (16)	0.0076 (13)	−0.0003 (14)	−0.0181 (13)
C3	0.0717 (16)	0.0541 (13)	0.0579 (13)	−0.0181 (13)	0.0123 (12)	−0.0147 (11)
C4	0.0442 (12)	0.0509 (12)	0.0445 (10)	−0.0034 (10)	−0.0024 (9)	−0.0037 (9)
C5	0.0472 (12)	0.0463 (11)	0.0414 (10)	0.0041 (10)	−0.0034 (10)	−0.0033 (9)
C6	0.0404 (10)	0.0380 (10)	0.0362 (9)	0.0020 (9)	0.0060 (9)	0.0016 (8)
C7	0.0474 (12)	0.0466 (12)	0.0393 (10)	0.0028 (10)	0.0014 (9)	0.0019 (9)
C8	0.0605 (14)	0.0473 (13)	0.0494 (11)	0.0046 (11)	0.0075 (11)	0.0149 (10)
C9	0.0615 (14)	0.0380 (11)	0.0631 (13)	−0.0092 (11)	0.0109 (12)	0.0033 (10)
C10	0.0514 (13)	0.0435 (11)	0.0495 (11)	−0.0049 (10)	0.0009 (10)	−0.0017 (10)
C11	0.0433 (11)	0.0371 (10)	0.0375 (9)	0.0009 (9)	0.0014 (9)	−0.0007 (8)
C12	0.0484 (13)	0.0415 (11)	0.0505 (11)	0.0008 (10)	−0.0063 (10)	−0.0021 (9)
C13	0.0431 (11)	0.0372 (10)	0.0474 (10)	−0.0079 (10)	−0.0071 (9)	0.0038 (9)
C14	0.0594 (14)	0.0453 (11)	0.0508 (11)	−0.0005 (11)	−0.0034 (11)	0.0011 (10)
C15	0.0819 (17)	0.0612 (14)	0.0519 (13)	−0.0120 (14)	0.0030 (12)	−0.0092 (11)
C16	0.0921 (19)	0.0694 (16)	0.0448 (11)	−0.0304 (16)	−0.0156 (12)	0.0042 (12)
C17	0.0756 (16)	0.0594 (15)	0.0627 (15)	−0.0169 (14)	−0.0253 (13)	0.0166 (12)
C18	0.0542 (13)	0.0455 (10)	0.0615 (13)	−0.0057 (11)	−0.0164 (11)	0.0050 (10)
C19	0.0592 (15)	0.0551 (13)	0.0521 (12)	0.0053 (12)	0.0052 (11)	0.0012 (10)
C20	0.0483 (12)	0.0414 (12)	0.0489 (11)	0.0009 (11)	0.0075 (10)	−0.0020 (9)
C21	0.0583 (14)	0.0427 (11)	0.0608 (13)	−0.0006 (11)	0.0109 (11)	−0.0001 (10)
C22	0.0692 (16)	0.0613 (14)	0.0605 (14)	0.0017 (13)	−0.0013 (12)	−0.0158 (13)
C23	0.0763 (17)	0.0746 (16)	0.0479 (12)	0.0274 (15)	−0.0007 (12)	−0.0090 (12)
C24	0.0869 (18)	0.0568 (14)	0.0573 (14)	0.0066 (14)	0.0209 (13)	0.0180 (11)
C25	0.0643 (15)	0.0546 (12)	0.0598 (13)	−0.0105 (12)	0.0098 (12)	0.0000 (11)

Geometric parameters (Å, º) top

N1—C19	1.460 (2)	C10—H10	0.9300
N1—C1	1.464 (2)	C11—C12	1.491 (3)
N1—C4	1.468 (2)	C12—C13	1.487 (3)
O1—C5	1.215 (2)	C13—C14	1.389 (3)
O2—C12	1.220 (2)	C13—C18	1.390 (3)
N2—C5	1.353 (2)	C14—C15	1.386 (3)
N2—C6	1.409 (2)	C14—H14	0.9300
N2—H2N	0.855 (19)	C15—C16	1.379 (3)
C1—C2	1.497 (3)	C15—H15	0.9300
C1—H1A	0.9700	C16—C17	1.379 (3)
C1—H1B	0.9700	C16—H16	0.9300
C2—C3	1.512 (3)	C17—C18	1.370 (3)
C2—H2A	0.9700	C17—H17	0.9300
C2—H2B	0.9700	C18—H18	0.9300
C3—C4	1.537 (3)	C19—C20	1.505 (3)
C3—H3A	0.9700	C19—H19A	0.9700
C3—H3B	0.9700	C19—H19B	0.9700
C4—C5	1.522 (3)	C20—C25	1.374 (3)
C4—H4	0.9800	C20—C21	1.377 (3)
C6—C7	1.385 (2)	C21—C22	1.366 (3)
C6—C11	1.410 (2)	C21—H21	0.9300
C7—C8	1.377 (3)	C22—C23	1.366 (3)
C7—H7	0.9300	C22—H22	0.9300
C8—C9	1.368 (3)	C23—C24	1.372 (3)
C8—H8	0.9300	C23—H23	0.9300
C9—C10	1.376 (3)	C24—C25	1.376 (3)
C9—H9	0.9300	C24—H24	0.9300
C10—C11	1.397 (3)	C25—H25	0.9300

C19—N1—C1	114.18 (16)	C10—C11—C6	118.45 (16)
C19—N1—C4	113.48 (15)	C10—C11—C12	119.44 (17)
C1—N1—C4	107.31 (14)	C6—C11—C12	121.85 (17)
C5—N2—C6	129.77 (17)	O2—C12—C13	119.48 (18)
C5—N2—H2N	115.1 (13)	O2—C12—C11	119.24 (17)
C6—N2—H2N	115.2 (13)	C13—C12—C11	121.26 (17)
N1—C1—C2	102.79 (17)	C14—C13—C18	119.06 (18)
N1—C1—H1A	111.2	C14—C13—C12	122.72 (18)
C2—C1—H1A	111.2	C18—C13—C12	118.07 (17)
N1—C1—H1B	111.2	C15—C14—C13	119.9 (2)
C2—C1—H1B	111.2	C15—C14—H14	120.1
H1A—C1—H1B	109.1	C13—C14—H14	120.1
C1—C2—C3	103.34 (19)	C16—C15—C14	120.1 (2)
C1—C2—H2A	111.1	C16—C15—H15	120.0
C3—C2—H2A	111.1	C14—C15—H15	120.0
C1—C2—H2B	111.1	C17—C16—C15	120.2 (2)
C3—C2—H2B	111.1	C17—C16—H16	119.9
H2A—C2—H2B	109.1	C15—C16—H16	119.9
C2—C3—C4	104.22 (17)	C18—C17—C16	119.8 (2)
C2—C3—H3A	110.9	C18—C17—H17	120.1
C4—C3—H3A	110.9	C16—C17—H17	120.1
C2—C3—H3B	110.9	C17—C18—C13	120.9 (2)
C4—C3—H3B	110.9	C17—C18—H18	119.5
H3A—C3—H3B	108.9	C13—C18—H18	119.5
N1—C4—C5	112.61 (16)	N1—C19—C20	111.80 (17)
N1—C4—C3	105.65 (15)	N1—C19—H19A	109.3
C5—C4—C3	112.77 (15)	C20—C19—H19A	109.3
N1—C4—H4	108.6	N1—C19—H19B	109.3
C5—C4—H4	108.6	C20—C19—H19B	109.3
C3—C4—H4	108.6	H19A—C19—H19B	107.9
O1—C5—N2	124.84 (19)	C25—C20—C21	117.60 (19)
O1—C5—C4	120.71 (18)	C25—C20—C19	121.75 (19)
N2—C5—C4	114.45 (17)	C21—C20—C19	120.64 (19)
C7—C6—N2	121.63 (17)	C22—C21—C20	122.0 (2)
C7—C6—C11	119.24 (17)	C22—C21—H21	119.0
N2—C6—C11	119.03 (16)	C20—C21—H21	119.0
C8—C7—C6	120.45 (19)	C23—C22—C21	119.7 (2)
C8—C7—H7	119.8	C23—C22—H22	120.2
C6—C7—H7	119.8	C21—C22—H22	120.2
C9—C8—C7	121.15 (18)	C22—C23—C24	119.6 (2)
C9—C8—H8	119.4	C22—C23—H23	120.2
C7—C8—H8	119.4	C24—C23—H23	120.2
C8—C9—C10	119.23 (18)	C23—C24—C25	120.1 (2)
C8—C9—H9	120.4	C23—C24—H24	119.9
C10—C9—H9	120.4	C25—C24—H24	119.9
C9—C10—C11	121.39 (18)	C20—C25—C24	121.0 (2)
C9—C10—H10	119.3	C20—C25—H25	119.5
C11—C10—H10	119.3	C24—C25—H25	119.5

C19—N1—C1—C2	163.29 (17)	C10—C11—C12—O2	−138.3 (2)
C4—N1—C1—C2	36.6 (2)	C6—C11—C12—O2	35.8 (3)
N1—C1—C2—C3	−40.8 (2)	C10—C11—C12—C13	40.5 (3)
C1—C2—C3—C4	29.9 (2)	C6—C11—C12—C13	−145.40 (19)
C19—N1—C4—C5	91.8 (2)	O2—C12—C13—C14	−154.8 (2)
C1—N1—C4—C5	−141.14 (18)	C11—C12—C13—C14	26.4 (3)
C19—N1—C4—C3	−144.72 (17)	O2—C12—C13—C18	20.7 (3)
C1—N1—C4—C3	−17.6 (2)	C11—C12—C13—C18	−158.10 (19)
C2—C3—C4—N1	−8.0 (2)	C18—C13—C14—C15	−0.5 (3)
C2—C3—C4—C5	115.4 (2)	C12—C13—C14—C15	174.96 (19)
C6—N2—C5—O1	10.4 (3)	C13—C14—C15—C16	1.0 (3)
C6—N2—C5—C4	−169.86 (17)	C14—C15—C16—C17	−0.1 (3)
N1—C4—C5—O1	−168.60 (18)	C15—C16—C17—C18	−1.3 (3)
C3—C4—C5—O1	71.9 (2)	C16—C17—C18—C13	1.8 (3)
N1—C4—C5—N2	11.6 (2)	C14—C13—C18—C17	−0.9 (3)
C3—C4—C5—N2	−107.8 (2)	C12—C13—C18—C17	−176.5 (2)
C5—N2—C6—C7	2.7 (3)	C1—N1—C19—C20	65.8 (2)
C5—N2—C6—C11	179.17 (19)	C4—N1—C19—C20	−170.79 (16)
N2—C6—C7—C8	174.78 (17)	N1—C19—C20—C25	−100.8 (2)
C11—C6—C7—C8	−1.7 (3)	N1—C19—C20—C21	78.0 (2)
C6—C7—C8—C9	−0.8 (3)	C25—C20—C21—C22	1.1 (3)
C7—C8—C9—C10	1.7 (3)	C19—C20—C21—C22	−177.7 (2)
C8—C9—C10—C11	−0.1 (3)	C20—C21—C22—C23	−1.0 (3)
C9—C10—C11—C6	−2.3 (3)	C21—C22—C23—C24	0.9 (3)
C9—C10—C11—C12	172.00 (18)	C22—C23—C24—C25	−1.0 (3)
C7—C6—C11—C10	3.1 (3)	C21—C20—C25—C24	−1.3 (3)
N2—C6—C11—C10	−173.41 (17)	C19—C20—C25—C24	177.5 (2)
C7—C6—C11—C12	−170.99 (17)	C23—C24—C25—C20	1.2 (3)
N2—C6—C11—C12	12.5 (3)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N2—H2N···O2	0.855 (19)	2.246 (17)	2.810 (2)	123.5 (15)
N2—H2N···N1	0.855 (19)	2.209 (18)	2.663 (2)	113.1 (14)

Experimental details

Crystal data
Chemical formula	C₂₅H₂₄N₂O₂
M_r	384.46
Crystal system, space group	Orthorhombic, P2₁2₁2₁
Temperature (K)	293
a, b, c (Å)	8.4036 (7), 11.2215 (8), 21.4182 (12)
V (Å³)	2019.8 (2)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.08
Crystal size (mm)	0.45 × 0.40 × 0.35

Data collection
Diffractometer	Enraf–Nonius CAD-4 four-circle diffractometer
Absorption correction	–
No. of measured, independent and observed [I > 2σ(I)] reflections	4479, 3740, 2372
R_int	0.013
(sin θ/λ)_max (Å⁻¹)	0.605

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.034, 0.084, 0.93
No. of reflections	3740
No. of parameters	266
H-atom treatment	H atoms treated by a mixture of independent and constrained refinement
Δρ_max, Δρ_min (e Å⁻³)	0.12, −0.12
Absolute structure	Flack (1983), 1587 Friedel pairs
Absolute structure parameter	−0.2 (15)

Computer programs: CAD-4 Software (Enraf–Nonius, 1989), XCAD (McArdle, 1999), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), ORTEPIII (Burnett & Johnson, 1996).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N2—H2N···O2	0.855 (19)	2.246 (17)	2.810 (2)	123.5 (15)
N2—H2N···N1	0.855 (19)	2.209 (18)	2.663 (2)	113.1 (14)

Acknowledgements

This research was supported by Kyungpook National University Research Fund, 2010.

References

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