1-(4-Bromo-benzo-yl)-2-phenyl-pyrrolidine-2-carboxamide.

In the title compound, C(18)H(17)BrN(2)O(2), which is a potential -human immunodeficiency virus type 1 (HIV-1) non-nucleoside reverse transcriptase inhibitor, the pyrrolidine ring exhibits an envelope conformation. In the crystal structure, inter-molecular N-H⋯O hydrogen bonds [N⋯O = 2.861 (3) Å] link the mol-ecules into centrosymmetric dimers.

Related literature

For related crystal structures, see: Karapetyan et al. (2002 ▶); Tamazyan et al. (2002 ▶, 2007 ▶). For details of the synthesis, see: Martirosyan et al. (2000 ▶, 2004 ▶). For potential pharmacological applications, see: De Clercq (1996 ▶).

Experimental

Crystal data

C18H17BrN2O2

M = 373.25

Monoclinic,

a = 9.5707 (19) Å

b = 13.738 (3) Å

c = 13.302 (3) Å

β = 96.99 (2)°

V = 1736.0 (6) Å3

Z = 4

Mo Kα radiation

μ = 2.38 mm−1

T = 260 (2) K

0.14 mm (radius)

Data collection

Enraf–Nonius CAD-4 diffractometer

Absorption correction: for a sphere (SHELXTL; Sheldrick, 2008 ▶) T min = 0.612, T max = 0.617

8356 measured reflections

4180 independent reflections

2941 reflections with I > 2σ(I)

R int = 0.050

3 standard reflections frequency: 180 min intensity decay: none

Refinement

R[F 2 > 2σ(F 2)] = 0.046

wR(F 2) = 0.118

S = 1.02

4180 reflections

216 parameters

10 restraints

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.87 e Å−3

Δρmin = −0.89 e Å−3

Data collection: DATACOL in CAD-4 (Enraf–Nonius, 1988 ▶); cell refinement: LS in CAD-4; data reduction: HELENA (Spek, 1997 ▶); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: SHELXTL (Sheldrick, 2008 ▶) and ORTEPII (Johnson, 1976 ▶); software used to prepare material for publication: SHELXTL.

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536808003954/cv2386sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536808003954/cv2386Isup2.hkl

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

C18H17BrN2O2	F000 = 760
Mr = 373.25	Dx = 1.428 Mg m−3
Monoclinic, P21/c	Mo Kα radiation λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 25 reflections
a = 9.5707 (19) Å	θ = 13–16º
b = 13.738 (3) Å	µ = 2.38 mm−1
c = 13.302 (3) Å	T = 260 (2) K
β = 96.99 (2)º	Spherical, colourless
V = 1736.0 (6) Å3	0.28 × 0.28 × 0.28 × 0.14 (radius) mm
Z = 4

Enraf–Nonius CAD-4 diffractometer	Rint = 0.050
Radiation source: fine-focus sealed tube	θmax = 28.0º
Monochromator: graphite	θmin = 2.1º
T = 260(2) K	h = −12→12
θ/2θ scans	k = 0→18
Absorption correction: for a sphere(SHELXTL; Sheldrick, 2008)	l = −17→17
Tmin = 0.612, Tmax = 0.617	3 standard reflections
8356 measured reflections	every 180 min
4180 independent reflections	intensity decay: none
2941 reflections with I > 2σ(I)

Refinement on F2	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.046	H atoms treated by a mixture of independent and constrained refinement
wR(F2) = 0.119	w = 1/[σ2(Fo2) + (0.0458P)2 + 1.2016P] where P = (Fo2 + 2Fc2)/3
S = 1.02	(Δ/σ)max = 0.001
4180 reflections	Δρmax = 0.87 e Å−3
216 parameters	Δρmin = −0.89 e Å−3
10 restraints	Extinction correction: none
Primary atom site location: structure-invariant direct methods

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.

	x	y	z	Uiso*/Ueq
Br1	0.68968 (4)	1.01480 (3)	0.85408 (3)	0.07187 (17)
C1	−0.0555 (2)	0.71666 (16)	0.64026 (16)	0.0217 (4)
N2	0.08435 (19)	0.75423 (14)	0.68588 (13)	0.0230 (4)
C3	0.1138 (3)	0.7265 (2)	0.79443 (18)	0.0372 (6)
H3A	0.1112	0.7831	0.8379	0.045*
H3B	0.2051	0.6955	0.8084	0.045*
C4	−0.0033 (3)	0.65609 (19)	0.80987 (18)	0.0330 (5)
H4A	−0.0257	0.6581	0.8790	0.040*
H4B	0.0215	0.5900	0.7935	0.040*
C5	−0.1249 (3)	0.69388 (18)	0.73599 (17)	0.0277 (5)
H5A	−0.1656	0.7520	0.7620	0.033*
H5B	−0.1977	0.6449	0.7224	0.033*
C6	−0.0375 (2)	0.62094 (16)	0.58089 (16)	0.0225 (5)
N7	0.0475 (3)	0.62518 (17)	0.50977 (16)	0.0310 (5)
H7A	0.060 (3)	0.572 (2)	0.477 (2)	0.026 (7)*
H7B	0.089 (3)	0.677 (2)	0.502 (2)	0.038 (8)*
O8	−0.1011 (2)	0.54709 (12)	0.60012 (14)	0.0357 (4)
C9	−0.1430 (2)	0.78995 (16)	0.57304 (17)	0.0245 (5)
C10	−0.1242 (3)	0.88979 (18)	0.5831 (2)	0.0333 (5)
H10	−0.0515	0.9139	0.6291	0.040*
C11	−0.2120 (3)	0.9539 (2)	0.5257 (2)	0.0448 (7)
H11	−0.1975	1.0206	0.5328	0.054*
C12	−0.3217 (3)	0.9190 (2)	0.4578 (2)	0.0484 (8)
H12	−0.3811	0.9621	0.4193	0.058*
C13	−0.3422 (3)	0.8208 (2)	0.4475 (2)	0.0454 (7)
H13	−0.4160	0.7973	0.4021	0.055*
C14	−0.2534 (3)	0.75578 (19)	0.50447 (19)	0.0341 (6)
H14	−0.2680	0.6891	0.4966	0.041*
C15	0.1780 (2)	0.79997 (16)	0.63414 (17)	0.0244 (5)
O16	0.16487 (18)	0.80521 (12)	0.54045 (12)	0.0298 (4)
C17	0.3019 (2)	0.84793 (17)	0.69371 (18)	0.0264 (5)
C18	0.4350 (3)	0.8311 (2)	0.6659 (2)	0.0356 (6)
H18	0.4463	0.7867	0.6148	0.043*
C19	0.5505 (3)	0.8797 (2)	0.7137 (2)	0.0441 (7)
H19	0.6397	0.8679	0.6955	0.053*
C20	0.5317 (3)	0.9461 (2)	0.7890 (2)	0.0412 (7)
C21	0.4003 (3)	0.9652 (2)	0.8166 (2)	0.0410 (6)
H21	0.3892	1.0110	0.8666	0.049*
C22	0.2853 (3)	0.91537 (19)	0.7691 (2)	0.0337 (6)
H22	0.1962	0.9271	0.7877	0.040*

	U11	U22	U33	U12	U13	U23
Br1	0.0470 (2)	0.0818 (3)	0.0793 (3)	−0.02922 (18)	−0.02262 (18)	0.0072 (2)
C1	0.0249 (10)	0.0220 (11)	0.0184 (10)	−0.0011 (8)	0.0038 (8)	−0.0017 (8)
N2	0.0263 (9)	0.0274 (10)	0.0154 (9)	−0.0030 (8)	0.0033 (7)	−0.0008 (7)
C3	0.0455 (15)	0.0498 (16)	0.0152 (11)	−0.0080 (12)	−0.0002 (10)	0.0018 (11)
C4	0.0441 (14)	0.0370 (14)	0.0188 (11)	−0.0031 (11)	0.0070 (10)	0.0039 (10)
C5	0.0329 (12)	0.0292 (12)	0.0229 (11)	0.0000 (10)	0.0108 (9)	−0.0012 (9)
C6	0.0273 (11)	0.0230 (11)	0.0170 (10)	0.0020 (9)	0.0014 (8)	0.0005 (8)
N7	0.0464 (13)	0.0213 (11)	0.0280 (11)	−0.0039 (10)	0.0159 (9)	−0.0048 (9)
O8	0.0492 (11)	0.0245 (9)	0.0365 (10)	−0.0080 (8)	0.0176 (8)	−0.0047 (7)
C9	0.0266 (11)	0.0263 (11)	0.0216 (11)	0.0033 (9)	0.0070 (9)	0.0019 (9)
C10	0.0359 (13)	0.0281 (13)	0.0367 (14)	0.0033 (10)	0.0076 (11)	0.0004 (11)
C11	0.0519 (17)	0.0289 (13)	0.0556 (19)	0.0102 (12)	0.0146 (15)	0.0123 (13)
C12	0.0484 (17)	0.0498 (18)	0.0472 (17)	0.0196 (14)	0.0065 (14)	0.0200 (14)
C13	0.0398 (15)	0.0563 (19)	0.0375 (16)	0.0111 (13)	−0.0064 (12)	0.0058 (13)
C14	0.0359 (13)	0.0332 (13)	0.0324 (13)	0.0040 (11)	0.0011 (11)	−0.0017 (11)
C15	0.0282 (11)	0.0221 (11)	0.0237 (11)	0.0022 (9)	0.0063 (9)	−0.0015 (9)
O16	0.0383 (9)	0.0314 (9)	0.0208 (8)	−0.0058 (7)	0.0078 (7)	−0.0010 (7)
C17	0.0257 (11)	0.0270 (11)	0.0267 (11)	0.0000 (9)	0.0042 (9)	0.0001 (10)
C18	0.0310 (13)	0.0372 (14)	0.0398 (15)	0.0024 (11)	0.0095 (11)	−0.0016 (11)
C19	0.0244 (12)	0.0528 (17)	0.0552 (18)	0.0022 (11)	0.0060 (12)	0.0068 (15)
C20	0.0299 (13)	0.0445 (15)	0.0453 (16)	−0.0118 (11)	−0.0107 (11)	0.0070 (13)
C21	0.0430 (15)	0.0394 (15)	0.0392 (15)	−0.0072 (12)	−0.0001 (12)	−0.0086 (12)
C22	0.0287 (12)	0.0357 (13)	0.0374 (14)	−0.0013 (10)	0.0064 (10)	−0.0093 (11)

Br1—C20	1.899 (3)	C10—C11	1.382 (4)
C1—N2	1.493 (3)	C10—H10	0.9300
C1—C9	1.527 (3)	C11—C12	1.385 (5)
C1—C5	1.538 (3)	C11—H11	0.9300
C1—C6	1.554 (3)	C12—C13	1.368 (5)
N2—C15	1.350 (3)	C12—H12	0.9300
N2—C3	1.487 (3)	C13—C14	1.392 (4)
C3—C4	1.513 (4)	C13—H13	0.9300
C3—H3A	0.9700	C14—H14	0.9300
C3—H3B	0.9700	C15—O16	1.239 (3)
C4—C5	1.520 (3)	C15—C17	1.496 (3)
C4—H4A	0.9700	C17—C18	1.388 (3)
C4—H4B	0.9700	C17—C22	1.389 (3)
C5—H5A	0.9700	C18—C19	1.378 (4)
C5—H5B	0.9700	C18—H18	0.9300
C6—O8	1.226 (3)	C19—C20	1.383 (4)
C6—N7	1.321 (3)	C19—H19	0.9300
N7—H7A	0.86 (3)	C20—C21	1.378 (4)
N7—H7B	0.83 (3)	C21—C22	1.383 (4)
C9—C10	1.388 (3)	C21—H21	0.9300
C9—C14	1.391 (3)	C22—H22	0.9300
N2—C1—C9	114.23 (18)	C11—C10—C9	121.0 (3)
N2—C1—C5	100.93 (17)	C11—C10—H10	119.5
C9—C1—C5	110.99 (18)	C9—C10—H10	119.5
N2—C1—C6	110.43 (17)	C10—C11—C12	120.1 (3)
C9—C1—C6	110.32 (17)	C10—C11—H11	120.0
C5—C1—C6	109.54 (18)	C12—C11—H11	120.0
C15—N2—C3	123.7 (2)	C13—C12—C11	119.6 (3)
C15—N2—C1	124.89 (18)	C13—C12—H12	120.2
C3—N2—C1	111.14 (18)	C11—C12—H12	120.2
N2—C3—C4	103.87 (19)	C12—C13—C14	120.6 (3)
N2—C3—H3A	111.0	C12—C13—H13	119.7
C4—C3—H3A	111.0	C14—C13—H13	119.7
N2—C3—H3B	111.0	C9—C14—C13	120.3 (3)
C4—C3—H3B	111.0	C9—C14—H14	119.8
H3A—C3—H3B	109.0	C13—C14—H14	119.8
C3—C4—C5	102.4 (2)	O16—C15—N2	123.2 (2)
C3—C4—H4A	111.3	O16—C15—C17	118.9 (2)
C5—C4—H4A	111.3	N2—C15—C17	117.9 (2)
C3—C4—H4B	111.3	C18—C17—C22	119.5 (2)
C5—C4—H4B	111.3	C18—C17—C15	118.6 (2)
H4A—C4—H4B	109.2	C22—C17—C15	121.5 (2)
C4—C5—C1	103.39 (19)	C19—C18—C17	120.5 (3)
C4—C5—H5A	111.1	C19—C18—H18	119.8
C1—C5—H5A	111.1	C17—C18—H18	119.8
C4—C5—H5B	111.1	C18—C19—C20	119.1 (3)
C1—C5—H5B	111.1	C18—C19—H19	120.5
H5A—C5—H5B	109.1	C20—C19—H19	120.5
O8—C6—N7	123.4 (2)	C21—C20—C19	121.5 (2)
O8—C6—C1	120.3 (2)	C21—C20—Br1	119.0 (2)
N7—C6—C1	116.3 (2)	C19—C20—Br1	119.5 (2)
C6—N7—H7A	117.1 (18)	C20—C21—C22	119.0 (3)
C6—N7—H7B	119 (2)	C20—C21—H21	120.5
H7A—N7—H7B	124 (3)	C22—C21—H21	120.5
C10—C9—C14	118.4 (2)	C21—C22—C17	120.4 (2)
C10—C9—C1	122.7 (2)	C21—C22—H22	119.8
C14—C9—C1	118.7 (2)	C17—C22—H22	119.8
C9—C1—N2—C15	−49.1 (3)	C1—C9—C10—C11	−175.3 (2)
C5—C1—N2—C15	−168.3 (2)	C9—C10—C11—C12	0.7 (4)
C6—C1—N2—C15	75.9 (3)	C10—C11—C12—C13	−0.2 (5)
C9—C1—N2—C3	136.3 (2)	C11—C12—C13—C14	−0.3 (5)
C5—C1—N2—C3	17.2 (2)	C10—C9—C14—C13	0.1 (4)
C6—C1—N2—C3	−98.6 (2)	C1—C9—C14—C13	175.0 (2)
C15—N2—C3—C4	−165.7 (2)	C12—C13—C14—C9	0.3 (4)
C1—N2—C3—C4	9.0 (3)	C3—N2—C15—O16	164.8 (2)
N2—C3—C4—C5	−31.7 (3)	C1—N2—C15—O16	−9.1 (3)
C3—C4—C5—C1	43.1 (2)	C3—N2—C15—C17	−16.3 (3)
N2—C1—C5—C4	−36.6 (2)	C1—N2—C15—C17	169.74 (19)
C9—C1—C5—C4	−158.09 (19)	O16—C15—C17—C18	−48.8 (3)
C6—C1—C5—C4	79.8 (2)	N2—C15—C17—C18	132.3 (2)
N2—C1—C6—O8	125.4 (2)	O16—C15—C17—C22	125.0 (3)
C9—C1—C6—O8	−107.4 (2)	N2—C15—C17—C22	−53.9 (3)
C5—C1—C6—O8	15.1 (3)	C22—C17—C18—C19	1.0 (4)
N2—C1—C6—N7	−55.3 (3)	C15—C17—C18—C19	174.9 (2)
C9—C1—C6—N7	71.9 (3)	C17—C18—C19—C20	−0.6 (4)
C5—C1—C6—N7	−165.6 (2)	C18—C19—C20—C21	−0.5 (4)
N2—C1—C9—C10	−23.9 (3)	C18—C19—C20—Br1	−179.2 (2)
C5—C1—C9—C10	89.4 (3)	C19—C20—C21—C22	1.2 (4)
C6—C1—C9—C10	−149.0 (2)	Br1—C20—C21—C22	179.9 (2)
N2—C1—C9—C14	161.4 (2)	C20—C21—C22—C17	−0.8 (4)
C5—C1—C9—C14	−85.3 (3)	C18—C17—C22—C21	−0.3 (4)
C6—C1—C9—C14	36.3 (3)	C15—C17—C22—C21	−174.0 (2)
C14—C9—C10—C11	−0.6 (4)

D—H···A	D—H	H···A	D···A	D—H···A
N7—H7b···O16	0.83 (2)	1.95 (3)	2.726 (3)	155 (3)
N7—H7a···O8i	0.86 (3)	2.00 (3)	2.861 (3)	176 (3)

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N7—H7b⋯O16	0.83 (2)	1.95 (3)	2.726 (3)	155 (3)
N7—H7a⋯O8i	0.86 (3)	2.00 (3)	2.861 (3)	176 (3)

Symmetry code: (i) .