(2R)-N-(2-Benzoyl-phen-yl)-1-benzyl-pyrrolidine-2-carboxamide.

In the title compound, C(25)H(24)N(2)O(2), the dihedral angle between the two benzene rings of the benzophenone moiety is 59.10 (6)°. An intra-molecular, bifurcated N-H⋯(O,N) hydrogen bond, which generates S(6) and S(5) rings, respectively, helps to establish the overall conformation of the mol-ecule.

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 = 384.46

Orthorhombic,

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[F 2 > 2σ(F 2)] = 0.034

wR(F 2) = 0.084

S = 0.93

3740 reflections

266 parameters

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.12 e Å−3

Δρmin = −0.12 e Å−3

Absolute structure: Flack (1983 ▶), 1587 Friedel pairs

Flack parameter: −0.2 (15)

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.

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S1600536811033836/hb5950sup1.cif

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

Supplementary material file. DOI: 10.1107/S1600536811033836/hb5950Isup3.cml

Additional supplementary materials: crystallographic information; 3D view; checkCIF report

C25H24N2O2	F(000) = 816
Mr = 384.46	Dx = 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

Enraf–Nonius CAD-4 four-circle diffractometer	Rint = 0.013
Radiation source: fine-focus sealed tube	θmax = 25.5°, θmin = 1.9°
graphite	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 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(Fo2) + (0.0442P)2] where P = (Fo2 + 2Fc2)/3
S = 0.93	(Δ/σ)max = 0.001
3740 reflections	Δρmax = 0.12 e Å−3
266 parameters	Δρmin = −0.12 e Å−3
0 restraints	Absolute structure: Flack (1983), 1587 Friedel pairs
Primary atom site location: structure-invariant direct methods	Flack parameter: −0.2 (15)

	x	y	z	Uiso*/Ueq
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*

	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)

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)

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)

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)