1-Benzyl-6-phenyl-imino-5-(pyrrol-2-yl-idene)hexa-hydro-pyrimidine-2,4-dione.

In the title compound, C(21)H(20)N(4)O(2), a potential anti-human immunodeficiency virus type 1 (HIV-1) non-nucleoside reverse transcriptase inhibitor, the pyrrolidine ring adopts an envelope conformation, while the hydrogenated pyrimidine ring adopts a weakly expressed twist conformation. The mol-ecules are connected into infinite chains via N-H⋯O hydrogen bonds.

Related literature

For related structures, see: Karapetyan et al. (2002 ▶); Tamazyan et al. (2002 ▶). For details of the pharmacological properties of similar compounds, see: De Clercq (1996 ▶).

Experimental

Crystal data

C21H20N4O2

M = 360.41

Triclinic,

a = 5.7844 (12) Å

b = 10.378 (2) Å

c = 15.595 (3) Å

α = 102.64 (3)°

β = 93.32 (3)°

γ = 102.45 (3)°

V = 886.6 (3) Å3

Z = 2

Mo Kα radiation

μ = 0.09 mm−1

T = 293 (2) K

0.3 × 0.27 × 0.25 mm

Data collection

Enraf–Nonius CAD-4 diffractometer

Absorption correction: none

5619 measured reflections

5144 independent reflections

2944 reflections with I > 2σ(I)

R int = 0.028

3 standard reflections frequency: 180 min intensity decay: none

Refinement

R[F 2 > 2σ(F 2)] = 0.065

wR(F 2) = 0.128

S = 1.04

5144 reflections

325 parameters

All H-atom parameters refined

Δρmax = 0.27 e Å−3

Δρmin = −0.26 e Å−3

Data collection: CAD-4 Software (Enraf–Nonius 1988 ▶); cell refinement: CAD-4 Software; 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/S1600536808001384/pv2060sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536808001384/pv2060Isup2.hkl

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

C21H20N4O2	Z = 2
Mr = 360.41	F000 = 380
Triclinic, P1	Dx = 1.350 Mg m−3
Hall symbol: -P 1	Mo Kα radiation λ = 0.71073 Å
a = 5.7844 (12) Å	Cell parameters from 22 reflections
b = 10.378 (2) Å	θ = 13–16º
c = 15.595 (3) Å	µ = 0.09 mm−1
α = 102.64 (3)º	T = 293 (2) K
β = 93.32 (3)º	Prism, colourless
γ = 102.45 (3)º	0.3 × 0.27 × 0.25 mm
V = 886.6 (3) Å3

Enraf–Nonius CAD-4 diffractometer	Rint = 0.028
Radiation source: fine-focus sealed tube	θmax = 30.0º
Monochromator: graphite	θmin = 1.4º
T = 293(2) K	h = 0→8
θ/2θ scans	k = −14→14
Absorption correction: none	l = −21→21
5619 measured reflections	3 standard reflections
5144 independent reflections	every 180 min
2944 reflections with I > 2σ(I)	intensity decay: none

Refinement on F2	Hydrogen site location: difference Fourier map
Least-squares matrix: full	All H-atom parameters refined
R[F2 > 2σ(F2)] = 0.065	w = 1/[σ2(Fo2) + (0.0198P)2 + 0.561P] where P = (Fo2 + 2Fc2)/3
wR(F2) = 0.128	(Δ/σ)max < 0.001
S = 1.04	Δρmax = 0.27 e Å−3
5144 reflections	Δρmin = −0.26 e Å−3
325 parameters	Extinction correction: SHELXL97 (Sheldrick, 2008), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.0124 (13)
Secondary atom site location: difference Fourier map

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
N1	0.4204 (3)	−0.03850 (16)	0.35608 (11)	0.0320 (4)
C2	0.2737 (4)	−0.0209 (2)	0.42132 (14)	0.0329 (5)
H3	0.163 (4)	0.120 (2)	0.4942 (16)	0.043 (7)*
N3	0.2672 (4)	0.11039 (18)	0.45813 (13)	0.0374 (5)
C4	0.4114 (4)	0.2259 (2)	0.44199 (13)	0.0312 (5)
C5	0.5484 (4)	0.20422 (19)	0.36835 (13)	0.0291 (4)
C6	0.5188 (4)	0.0671 (2)	0.31427 (14)	0.0295 (4)
O7	0.4116 (3)	0.33653 (15)	0.49159 (10)	0.0430 (4)
O8	0.1540 (3)	−0.11624 (15)	0.44595 (11)	0.0469 (4)
C9	0.7255 (4)	0.3145 (2)	0.35785 (13)	0.0300 (4)
H10	0.638 (4)	0.464 (2)	0.4363 (16)	0.044 (7)*
N10	0.7427 (4)	0.44206 (18)	0.39838 (13)	0.0393 (5)
C11	0.9511 (5)	0.5384 (2)	0.3816 (2)	0.0465 (6)
H11A	1.017 (5)	0.610 (3)	0.438 (2)	0.075 (9)*
H11B	0.906 (5)	0.585 (3)	0.3357 (18)	0.060 (8)*
C12	1.1099 (5)	0.4461 (3)	0.34836 (19)	0.0462 (6)
H12A	1.208 (5)	0.435 (3)	0.4041 (19)	0.066 (9)*
H12B	1.215 (5)	0.476 (3)	0.3058 (17)	0.058 (8)*
C13	0.9361 (4)	0.3101 (3)	0.30583 (17)	0.0401 (6)
H13A	0.993 (5)	0.228 (3)	0.3025 (17)	0.054 (8)*
H13B	0.890 (5)	0.310 (3)	0.245 (2)	0.071 (9)*
N14	0.5687 (3)	0.02327 (18)	0.23576 (12)	0.0367 (4)
C15	0.5951 (4)	0.0974 (2)	0.16998 (14)	0.0342 (5)
C16	0.4413 (5)	0.1784 (3)	0.15504 (17)	0.0457 (6)
H16	0.325 (4)	0.192 (2)	0.1957 (16)	0.048 (7)*
C17	0.4605 (6)	0.2394 (3)	0.08445 (19)	0.0578 (8)
H17	0.351 (5)	0.292 (3)	0.0734 (19)	0.069 (9)*
C18	0.6315 (6)	0.2211 (3)	0.02769 (18)	0.0593 (8)
H18	0.646 (5)	0.263 (3)	−0.024 (2)	0.072 (9)*
C19	0.7829 (5)	0.1407 (3)	0.04185 (17)	0.0533 (7)
H19	0.904 (5)	0.127 (3)	0.002 (2)	0.072 (9)*
C20	0.7642 (5)	0.0783 (3)	0.11150 (16)	0.0439 (6)
H20	0.866 (5)	0.023 (3)	0.1218 (17)	0.056 (8)*
C21	0.4193 (4)	−0.1793 (2)	0.31229 (15)	0.0350 (5)
H21A	0.575 (4)	−0.179 (2)	0.2917 (14)	0.033 (6)*
H21B	0.403 (4)	−0.229 (2)	0.3603 (15)	0.037 (6)*
C22	0.2243 (4)	−0.2461 (2)	0.23746 (14)	0.0334 (5)
C23	0.2296 (5)	−0.3733 (2)	0.18596 (16)	0.0417 (6)
H23	0.367 (5)	−0.412 (3)	0.1979 (17)	0.058 (8)*
C24	0.0439 (5)	−0.4443 (3)	0.12153 (18)	0.0528 (7)
H24	0.049 (5)	−0.533 (3)	0.0869 (17)	0.059 (8)*
C25	−0.1440 (5)	−0.3884 (3)	0.10493 (18)	0.0546 (7)
H25	−0.276 (5)	−0.439 (3)	0.0577 (18)	0.064 (8)*
C26	−0.1472 (5)	−0.2606 (3)	0.15307 (17)	0.0482 (6)
H26	−0.285 (5)	−0.219 (3)	0.1429 (17)	0.061 (8)*
C27	0.0355 (5)	−0.1909 (2)	0.21906 (16)	0.0415 (6)
H27	0.030 (4)	−0.103 (2)	0.2539 (15)	0.038 (6)*

	U11	U22	U33	U12	U13	U23
N1	0.0374 (10)	0.0241 (8)	0.0323 (9)	0.0033 (7)	0.0113 (8)	0.0042 (7)
C2	0.0368 (12)	0.0286 (10)	0.0328 (11)	0.0050 (9)	0.0096 (9)	0.0071 (9)
N3	0.0432 (11)	0.0282 (9)	0.0404 (11)	0.0049 (8)	0.0219 (9)	0.0063 (8)
C4	0.0339 (12)	0.0288 (10)	0.0307 (11)	0.0062 (9)	0.0062 (9)	0.0066 (9)
C5	0.0318 (11)	0.0260 (10)	0.0284 (10)	0.0030 (8)	0.0086 (9)	0.0062 (8)
C6	0.0288 (11)	0.0259 (10)	0.0330 (11)	0.0030 (8)	0.0090 (9)	0.0072 (8)
O7	0.0566 (11)	0.0281 (8)	0.0424 (9)	0.0071 (7)	0.0204 (8)	0.0032 (7)
O8	0.0581 (11)	0.0319 (8)	0.0532 (10)	0.0052 (8)	0.0276 (9)	0.0153 (7)
C9	0.0301 (11)	0.0318 (11)	0.0268 (10)	0.0046 (9)	0.0026 (8)	0.0069 (8)
N10	0.0418 (12)	0.0279 (9)	0.0462 (12)	0.0024 (8)	0.0149 (10)	0.0079 (8)
C11	0.0464 (15)	0.0323 (12)	0.0540 (16)	−0.0060 (11)	0.0077 (13)	0.0106 (12)
C12	0.0374 (14)	0.0424 (14)	0.0541 (16)	−0.0033 (11)	0.0071 (12)	0.0136 (12)
C13	0.0340 (13)	0.0371 (13)	0.0453 (14)	0.0011 (10)	0.0120 (11)	0.0067 (11)
N14	0.0441 (11)	0.0309 (9)	0.0336 (10)	0.0047 (8)	0.0141 (8)	0.0063 (8)
C15	0.0361 (12)	0.0310 (11)	0.0289 (11)	−0.0022 (9)	0.0075 (9)	0.0022 (9)
C16	0.0410 (14)	0.0533 (15)	0.0411 (14)	0.0068 (12)	0.0079 (12)	0.0111 (11)
C17	0.0546 (18)	0.0641 (18)	0.0554 (17)	0.0070 (15)	−0.0062 (14)	0.0257 (15)
C18	0.066 (2)	0.0638 (18)	0.0395 (15)	−0.0107 (15)	−0.0006 (14)	0.0215 (13)
C19	0.0581 (18)	0.0554 (16)	0.0340 (13)	−0.0086 (14)	0.0138 (13)	0.0035 (12)
C20	0.0500 (15)	0.0402 (13)	0.0382 (13)	0.0056 (12)	0.0165 (12)	0.0045 (11)
C21	0.0407 (13)	0.0280 (11)	0.0371 (12)	0.0089 (10)	0.0116 (10)	0.0065 (9)
C22	0.0390 (12)	0.0267 (10)	0.0333 (11)	0.0026 (9)	0.0114 (10)	0.0081 (8)
C23	0.0543 (16)	0.0312 (12)	0.0383 (13)	0.0081 (11)	0.0136 (12)	0.0050 (10)
C24	0.0671 (19)	0.0366 (14)	0.0437 (14)	0.0029 (13)	0.0119 (14)	−0.0061 (11)
C25	0.0545 (18)	0.0550 (17)	0.0405 (14)	−0.0035 (14)	0.0009 (13)	−0.0001 (12)
C26	0.0418 (15)	0.0514 (15)	0.0472 (15)	0.0050 (12)	0.0026 (12)	0.0094 (12)
C27	0.0456 (14)	0.0316 (12)	0.0443 (13)	0.0068 (10)	0.0089 (11)	0.0040 (10)

N1—C2	1.369 (3)	C15—C16	1.391 (3)
N1—C6	1.427 (2)	C15—C20	1.392 (3)
N1—C21	1.470 (3)	C16—C17	1.383 (4)
C2—O8	1.228 (2)	C16—H16	0.96 (3)
C2—N3	1.368 (3)	C17—C18	1.381 (4)
N3—C4	1.386 (3)	C17—H17	0.95 (3)
N3—H3	0.86 (2)	C18—C19	1.373 (4)
C4—O7	1.236 (2)	C18—H18	0.99 (3)
C4—C5	1.437 (3)	C19—C20	1.379 (4)
C5—C9	1.408 (3)	C19—H19	0.97 (3)
C5—C6	1.455 (3)	C20—H20	0.93 (3)
C6—N14	1.282 (3)	C21—C22	1.507 (3)
C9—N10	1.316 (3)	C21—H21A	0.97 (2)
C9—C13	1.506 (3)	C21—H21B	0.99 (2)
N10—C11	1.467 (3)	C22—C27	1.381 (3)
N10—H10	0.90 (2)	C22—C23	1.395 (3)
C11—C12	1.499 (4)	C23—C24	1.384 (4)
C11—H11A	1.01 (3)	C23—H23	0.99 (3)
C11—H11B	1.00 (3)	C24—C25	1.375 (4)
C12—C13	1.531 (3)	C24—H24	0.96 (3)
C12—H12A	1.05 (3)	C25—C26	1.379 (4)
C12—H12B	0.98 (3)	C25—H25	1.00 (3)
C13—H13A	0.97 (3)	C26—C27	1.384 (4)
C13—H13B	0.97 (3)	C26—H26	1.00 (3)
N14—C15	1.407 (3)	C27—H27	0.96 (2)
C2—N1—C6	122.57 (17)	C16—C15—C20	118.3 (2)
C2—N1—C21	116.70 (17)	C16—C15—N14	122.3 (2)
C6—N1—C21	118.51 (17)	C20—C15—N14	119.0 (2)
O8—C2—N3	121.31 (19)	C17—C16—C15	120.3 (3)
O8—C2—N1	122.72 (19)	C17—C16—H16	121.3 (15)
N3—C2—N1	115.97 (18)	C15—C16—H16	118.4 (15)
C2—N3—C4	126.16 (19)	C18—C17—C16	120.8 (3)
C2—N3—H3	115.4 (16)	C18—C17—H17	119.4 (18)
C4—N3—H3	118.5 (16)	C16—C17—H17	119.7 (18)
O7—C4—N3	117.81 (19)	C19—C18—C17	119.1 (3)
O7—C4—C5	126.25 (19)	C19—C18—H18	119.3 (17)
N3—C4—C5	115.94 (18)	C17—C18—H18	121.6 (17)
C9—C5—C4	118.04 (18)	C18—C19—C20	120.6 (3)
C9—C5—C6	122.50 (18)	C18—C19—H19	120.2 (18)
C4—C5—C6	119.06 (17)	C20—C19—H19	119.2 (18)
N14—C6—N1	113.57 (18)	C19—C20—C15	120.8 (3)
N14—C6—C5	131.61 (19)	C19—C20—H20	121.4 (16)
N1—C6—C5	114.81 (17)	C15—C20—H20	117.7 (16)
N10—C9—C5	124.5 (2)	N1—C21—C22	115.08 (19)
N10—C9—C13	107.55 (19)	N1—C21—H21A	107.5 (13)
C5—C9—C13	127.79 (19)	C22—C21—H21A	110.5 (13)
C9—N10—C11	114.7 (2)	N1—C21—H21B	104.6 (13)
C9—N10—H10	120.3 (16)	C22—C21—H21B	110.5 (13)
C11—N10—H10	124.8 (16)	H21A—C21—H21B	108.3 (18)
N10—C11—C12	101.68 (19)	C27—C22—C23	118.0 (2)
N10—C11—H11A	109.7 (17)	C27—C22—C21	123.7 (2)
C12—C11—H11A	115.6 (17)	C23—C22—C21	118.2 (2)
N10—C11—H11B	110.5 (16)	C24—C23—C22	120.5 (3)
C12—C11—H11B	111.4 (16)	C24—C23—H23	121.3 (16)
H11A—C11—H11B	108 (2)	C22—C23—H23	118.2 (16)
C11—C12—C13	103.9 (2)	C25—C24—C23	120.6 (3)
C11—C12—H12A	106.9 (15)	C25—C24—H24	119.8 (16)
C13—C12—H12A	108.7 (15)	C23—C24—H24	119.5 (16)
C11—C12—H12B	115.1 (15)	C24—C25—C26	119.6 (3)
C13—C12—H12B	110.6 (15)	C24—C25—H25	120.6 (16)
H12A—C12—H12B	111 (2)	C26—C25—H25	119.9 (16)
C9—C13—C12	103.0 (2)	C25—C26—C27	119.9 (3)
C9—C13—H13A	113.3 (15)	C25—C26—H26	120.6 (16)
C12—C13—H13A	117.7 (16)	C27—C26—H26	119.4 (16)
C9—C13—H13B	109.5 (18)	C22—C27—C26	121.4 (2)
C12—C13—H13B	107.9 (17)	C22—C27—H27	118.9 (14)
H13A—C13—H13B	105 (2)	C26—C27—H27	119.7 (14)
C6—N14—C15	125.54 (19)
C6—N1—C2—O8	166.1 (2)	N10—C9—C13—C12	18.0 (3)
C21—N1—C2—O8	3.3 (3)	C5—C9—C13—C12	−157.6 (2)
C6—N1—C2—N3	−13.8 (3)	C11—C12—C13—C9	−28.8 (3)
C21—N1—C2—N3	−176.6 (2)	N1—C6—N14—C15	158.8 (2)
O8—C2—N3—C4	173.1 (2)	C5—C6—N14—C15	−22.4 (4)
N1—C2—N3—C4	−7.0 (3)	C6—N14—C15—C16	−42.4 (3)
C2—N3—C4—O7	−167.7 (2)	C6—N14—C15—C20	144.7 (2)
C2—N3—C4—C5	12.0 (3)	C20—C15—C16—C17	−1.0 (4)
O7—C4—C5—C9	9.8 (3)	N14—C15—C16—C17	−174.0 (2)
N3—C4—C5—C9	−169.9 (2)	C15—C16—C17—C18	0.1 (4)
O7—C4—C5—C6	−177.4 (2)	C16—C17—C18—C19	0.3 (4)
N3—C4—C5—C6	3.0 (3)	C17—C18—C19—C20	0.3 (4)
C2—N1—C6—N14	−154.0 (2)	C18—C19—C20—C15	−1.3 (4)
C21—N1—C6—N14	8.5 (3)	C16—C15—C20—C19	1.6 (3)
C2—N1—C6—C5	27.1 (3)	N14—C15—C20—C19	174.8 (2)
C21—N1—C6—C5	−170.4 (2)	C2—N1—C21—C22	84.4 (2)
C9—C5—C6—N14	−26.9 (4)	C6—N1—C21—C22	−79.1 (2)
C4—C5—C6—N14	160.5 (2)	N1—C21—C22—C27	−10.3 (3)
C9—C5—C6—N1	151.8 (2)	N1—C21—C22—C23	172.27 (19)
C4—C5—C6—N1	−20.7 (3)	C27—C22—C23—C24	−3.3 (3)
C4—C5—C9—N10	−15.1 (3)	C21—C22—C23—C24	174.3 (2)
C6—C5—C9—N10	172.4 (2)	C22—C23—C24—C25	2.5 (4)
C4—C5—C9—C13	159.9 (2)	C23—C24—C25—C26	−0.1 (4)
C6—C5—C9—C13	−12.7 (4)	C24—C25—C26—C27	−1.6 (4)
C5—C9—N10—C11	176.1 (2)	C23—C22—C27—C26	1.6 (3)
C13—C9—N10—C11	0.3 (3)	C21—C22—C27—C26	−175.8 (2)
C9—N10—C11—C12	−18.9 (3)	C25—C26—C27—C22	0.8 (4)
N10—C11—C12—C13	28.4 (3)

D—H···A	D—H	H···A	D···A	D—H···A
N10—H10···O7	0.90 (2)	2.03 (2)	2.664 (3)	127 (2)
N10—H10···O7i	0.90 (2)	2.22 (2)	2.891 (3)	131 (2)
N3—H3···O8ii	0.86 (2)	2.10 (2)	2.937 (3)	165 (2)

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N10—H10⋯O7	0.90 (2)	2.03 (2)	2.664 (3)	127 (2)
N10—H10⋯O7i	0.90 (2)	2.22 (2)	2.891 (3)	131 (2)
N3—H3⋯O8ii	0.86 (2)	2.10 (2)	2.937 (3)	165 (2)

Symmetry codes: (i) ; (ii) .