1-Eth-oxy-methyl-5-methyl-9-phenyl-6,7,8,9-tetra-hydro-1H-pyrimido[4,5-b][1,4]diazepine-2,4(3H,5H)-dione.

The title compound, C(17)H(22)N(4)O(3), comprises a 1,4-diazepine ring in a twist-boat conformation fused to a pyrimidine ring. The dihedral angle between the pyrimidine and phenyl rings is 80.8 (1)°. The crystal packing features N-H⋯O and C-H⋯O hydrogen bonds.

Related literature

For the preparation of 2,4-dimeth­oxy-5-methyl-9-phenyl-8,9-dihydro-5H- pyrimido[4,5-b][1,4]diazepin-6(7H), see: Li et al. (2012 ▶). For the biological activity of compounds with a pyrimidodiazepine scaffold, see: Ferreira et al. (2009 ▶); Gracias et al. (2008 ▶); Insuasty et al. (2008 ▶); Chen et al. (2012 ▶). The title compound was obtained during work on the structural modification of our previously reported HIV-1 reverse transcriptase inhibitor, see: Wang et al. (2006 ▶).

Experimental

Crystal data

C17H22N4O3

M = 330.39

Monoclinic,

a = 13.831 (3) Å

b = 8.9904 (18) Å

c = 14.978 (3) Å

β = 112.79 (3)°

V = 1717.1 (6) Å3

Z = 4

Mo Kα radiation

μ = 0.09 mm−1

T = 298 K

0.40 × 0.30 × 0.30 mm

Data collection

Rigaku R-AXIS RAPID IPdiffractometer

Absorption correction: multi-scan (ABSCOR; Higashi, 1995 ▶) T min = 0.965, T max = 0.974

7151 measured reflections

3921 independent reflections

1601 reflections with I > 2σ(I)

R int = 0.041

Refinement

R[F 2 > 2σ(F 2)] = 0.079

wR(F 2) = 0.250

S = 0.86

3921 reflections

218 parameters

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.70 e Å−3

Δρmin = −0.59 e Å−3

Data collection: RAPID-AUTO (Rigaku, 2000 ▶); cell refinement: RAPID-AUTO; data reduction: CrystalStructure (Rigaku/MSC, 2000 ▶); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: SHELXTL (Sheldrick, 2008 ▶); software used to prepare material for publication: SHELXL97.

Crystal structure: contains datablock(s) I, global. DOI: 10.1107/S1600536812014985/kp2397sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536812014985/kp2397Isup2.hkl

Supplementary material file. DOI: 10.1107/S1600536812014985/kp2397Isup3.cdx

Supplementary material file. DOI: 10.1107/S1600536812014985/kp2397Isup4.cdx

Supplementary material file. DOI: 10.1107/S1600536812014985/kp2397Isup5.cml

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

C17H22N4O3	F(000) = 704
Mr = 330.39	Dx = 1.278 Mg m−3
Monoclinic, P21/n	Mo Kα radiation, λ = 0.71073 Å
a = 13.831 (3) Å	θ = 2.6–27.5°
b = 8.9904 (18) Å	µ = 0.09 mm−1
c = 14.978 (3) Å	T = 298 K
β = 112.79 (3)°	Block, colourless
V = 1717.1 (6) Å3	0.40 × 0.30 × 0.30 mm
Z = 4

Rigaku R-AXIS RAPID IP diffractometer	3921 independent reflections
Radiation source: fine-focus sealed tube	1601 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.041
Detector resolution: 10.00 pixels mm-1	θmax = 27.5°, θmin = 2.6°
Ω scans	h = −17→17
Absorption correction: multi-scan (ABSCOR; Higashi, 1995)	k = −11→11
Tmin = 0.965, Tmax = 0.974	l = −19→19
7151 measured reflections

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)] = 0.079	H atoms treated by a mixture of independent and constrained refinement
wR(F2) = 0.250	w = 1/[σ2(Fo2) + (0.151P)2] where P = (Fo2 + 2Fc2)/3
S = 0.86	(Δ/σ)max = 0.004
3921 reflections	Δρmax = 0.70 e Å−3
218 parameters	Δρmin = −0.59 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: 0.062 (7)

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
C1	0.3598 (3)	0.0927 (4)	0.1226 (2)	0.0529 (8)
C2	0.3869 (3)	0.1940 (4)	0.2044 (2)	0.0509 (8)
C3	0.2088 (3)	0.2532 (6)	0.1902 (3)	0.1021 (16)
H3A	0.2026	0.2844	0.1269	0.153*
H3B	0.1855	0.3317	0.2205	0.153*
H3C	0.1665	0.1664	0.1847	0.153*
C4	0.3437 (4)	0.1949 (5)	0.3481 (3)	0.0979 (15)
H4A	0.3072	0.1067	0.3558	0.118*
H4B	0.3181	0.2784	0.3738	0.118*
C5	0.4578 (4)	0.1761 (5)	0.4074 (3)	0.0916 (15)
H5A	0.4665	0.1515	0.4731	0.110*
H5B	0.4834	0.0925	0.3820	0.110*
C6	0.5239 (4)	0.3082 (5)	0.4105 (3)	0.0927 (15)
H6A	0.5043	0.3886	0.4433	0.111*
H6B	0.5966	0.2836	0.4485	0.111*
C7	0.4813 (3)	0.2614 (3)	0.2368 (2)	0.0481 (8)
C8	0.5306 (3)	0.1445 (4)	0.1140 (2)	0.0540 (9)
C9	0.6648 (3)	0.2706 (4)	0.2460 (2)	0.0624 (10)
H9A	0.7025	0.2656	0.2034	0.075*
H9B	0.6723	0.3699	0.2732	0.075*
C10	0.7968 (4)	0.1714 (8)	0.3765 (4)	0.1291 (15)
H10A	0.8076	0.2688	0.4067	0.155*
H10B	0.8390	0.1673	0.3377	0.155*
C11	0.8383 (4)	0.0601 (7)	0.4539 (4)	0.1291 (15)
H11A	0.7953	0.0577	0.4911	0.194*
H11B	0.9088	0.0860	0.4954	0.194*
H11C	0.8379	−0.0360	0.4259	0.194*
C12	0.5293 (2)	0.5115 (4)	0.3007 (2)	0.0483 (8)
C13	0.5958 (3)	0.5994 (4)	0.3752 (3)	0.0632 (10)
H13	0.6339	0.5586	0.4358	0.076*
C14	0.6045 (3)	0.7501 (4)	0.3579 (3)	0.0729 (11)
H14	0.6477	0.8101	0.4081	0.087*
C15	0.5513 (3)	0.8117 (4)	0.2692 (3)	0.0785 (12)
H15	0.5590	0.9121	0.2586	0.094*
C16	0.4866 (3)	0.7244 (4)	0.1964 (3)	0.0732 (11)
H16	0.4497	0.7662	0.1359	0.088*
C17	0.4749 (3)	0.5758 (4)	0.2106 (2)	0.0590 (9)
H17	0.4305	0.5179	0.1598	0.071*
H1A	0.420 (3)	0.018 (4)	0.027 (3)	0.070 (10)*
N1	0.4323 (2)	0.0844 (3)	0.07953 (19)	0.0533 (7)
N2	0.55515 (19)	0.2347 (3)	0.19371 (18)	0.0505 (7)
N3	0.5151 (2)	0.3599 (3)	0.31555 (17)	0.0561 (8)
N4	0.3169 (2)	0.2189 (4)	0.2482 (2)	0.0805 (10)
O1	0.2790 (2)	0.0204 (3)	0.08886 (18)	0.0761 (8)
O2	0.59235 (19)	0.1200 (3)	0.07421 (17)	0.0757 (8)
O3	0.7038 (2)	0.1625 (4)	0.3210 (2)	0.1100 (12)

	U11	U22	U33	U12	U13	U23
C1	0.067 (2)	0.046 (2)	0.0511 (18)	−0.0031 (17)	0.0282 (17)	−0.0018 (16)
C2	0.061 (2)	0.0484 (19)	0.0545 (18)	−0.0016 (16)	0.0342 (16)	−0.0008 (15)
C3	0.078 (3)	0.119 (4)	0.127 (4)	0.010 (3)	0.060 (3)	−0.012 (3)
C4	0.135 (4)	0.098 (4)	0.098 (3)	0.014 (3)	0.085 (3)	0.013 (3)
C5	0.143 (4)	0.081 (3)	0.076 (3)	0.009 (3)	0.070 (3)	0.016 (2)
C6	0.152 (4)	0.084 (3)	0.053 (2)	−0.028 (3)	0.052 (3)	−0.007 (2)
C7	0.067 (2)	0.0424 (18)	0.0439 (16)	0.0054 (16)	0.0318 (16)	0.0012 (14)
C8	0.069 (2)	0.052 (2)	0.0523 (18)	0.0014 (17)	0.0350 (17)	−0.0020 (17)
C9	0.063 (2)	0.070 (3)	0.057 (2)	0.0059 (19)	0.0268 (17)	0.0037 (19)
C10	0.106 (3)	0.161 (4)	0.096 (3)	0.004 (3)	0.013 (2)	0.026 (3)
C11	0.106 (3)	0.161 (4)	0.096 (3)	0.004 (3)	0.013 (2)	0.026 (3)
C12	0.0493 (18)	0.051 (2)	0.0492 (18)	0.0033 (15)	0.0242 (15)	−0.0057 (16)
C13	0.066 (2)	0.066 (3)	0.060 (2)	−0.0027 (19)	0.0265 (18)	−0.0080 (19)
C14	0.076 (3)	0.060 (3)	0.089 (3)	−0.014 (2)	0.039 (2)	−0.024 (2)
C15	0.094 (3)	0.048 (2)	0.105 (3)	−0.002 (2)	0.051 (3)	0.001 (2)
C16	0.085 (3)	0.058 (3)	0.076 (3)	0.009 (2)	0.031 (2)	0.008 (2)
C17	0.062 (2)	0.054 (2)	0.061 (2)	0.0036 (17)	0.0227 (18)	−0.0037 (18)
N1	0.0655 (19)	0.0505 (17)	0.0509 (16)	−0.0029 (14)	0.0304 (14)	−0.0101 (14)
N2	0.0560 (17)	0.0541 (17)	0.0502 (15)	−0.0006 (13)	0.0303 (13)	−0.0030 (13)
N3	0.082 (2)	0.0504 (18)	0.0420 (14)	−0.0028 (14)	0.0310 (14)	−0.0031 (13)
N4	0.075 (2)	0.114 (3)	0.070 (2)	−0.0053 (19)	0.0478 (18)	−0.0150 (19)
O1	0.0730 (17)	0.0815 (19)	0.0795 (17)	−0.0219 (15)	0.0360 (14)	−0.0220 (15)
O2	0.0804 (18)	0.088 (2)	0.0769 (17)	−0.0075 (14)	0.0507 (15)	−0.0232 (14)
O3	0.073 (2)	0.168 (3)	0.0755 (19)	0.009 (2)	0.0146 (16)	0.035 (2)

C1—O1	1.221 (4)	C9—O3	1.424 (4)
C1—N1	1.389 (4)	C9—N2	1.448 (4)
C1—C2	1.454 (4)	C9—H9A	0.9700
C2—C7	1.347 (4)	C9—H9B	0.9700
C2—N4	1.382 (4)	C10—O3	1.235 (5)
C3—N4	1.442 (5)	C10—C11	1.470 (7)
C3—H3A	0.9600	C10—H10A	0.9700
C3—H3B	0.9600	C10—H10B	0.9700
C3—H3C	0.9600	C11—H11A	0.9600
C4—N4	1.412 (5)	C11—H11B	0.9600
C4—C5	1.491 (6)	C11—H11C	0.9600
C4—H4A	0.9700	C12—C13	1.386 (4)
C4—H4B	0.9700	C12—C17	1.392 (4)
C5—C6	1.488 (6)	C12—N3	1.407 (4)
C5—H5A	0.9700	C13—C14	1.393 (5)
C5—H5B	0.9700	C13—H13	0.9300
C6—N3	1.456 (4)	C14—C15	1.362 (5)
C6—H6A	0.9700	C14—H14	0.9300
C6—H6B	0.9700	C15—C16	1.360 (5)
C7—N3	1.403 (4)	C15—H15	0.9300
C7—N2	1.424 (4)	C16—C17	1.372 (5)
C8—O2	1.235 (4)	C16—H16	0.9300
C8—N1	1.366 (4)	C17—H17	0.9300
C8—N2	1.373 (4)	N1—H1A	0.95 (4)
O1—C1—N1	119.3 (3)	O3—C10—H10A	107.7
O1—C1—C2	125.4 (3)	C11—C10—H10A	107.7
N1—C1—C2	115.3 (3)	O3—C10—H10B	107.7
C7—C2—N4	121.0 (3)	C11—C10—H10B	107.7
C7—C2—C1	118.9 (3)	H10A—C10—H10B	107.1
N4—C2—C1	120.1 (3)	C10—C11—H11A	109.5
N4—C3—H3A	109.5	C10—C11—H11B	109.5
N4—C3—H3B	109.5	H11A—C11—H11B	109.5
H3A—C3—H3B	109.5	C10—C11—H11C	109.5
N4—C3—H3C	109.5	H11A—C11—H11C	109.5
H3A—C3—H3C	109.5	H11B—C11—H11C	109.5
H3B—C3—H3C	109.5	C13—C12—C17	119.0 (3)
N4—C4—C5	115.5 (3)	C13—C12—N3	121.0 (3)
N4—C4—H4A	108.4	C17—C12—N3	120.0 (3)
C5—C4—H4A	108.4	C12—C13—C14	118.9 (3)
N4—C4—H4B	108.4	C12—C13—H13	120.6
C5—C4—H4B	108.4	C14—C13—H13	120.6
H4A—C4—H4B	107.5	C15—C14—C13	121.6 (4)
C6—C5—C4	115.1 (4)	C15—C14—H14	119.2
C6—C5—H5A	108.5	C13—C14—H14	119.2
C4—C5—H5A	108.5	C16—C15—C14	119.1 (4)
C6—C5—H5B	108.5	C16—C15—H15	120.4
C4—C5—H5B	108.5	C14—C15—H15	120.4
H5A—C5—H5B	107.5	C15—C16—C17	121.2 (4)
N3—C6—C5	114.0 (3)	C15—C16—H16	119.4
N3—C6—H6A	108.8	C17—C16—H16	119.4
C5—C6—H6A	108.8	C16—C17—C12	120.2 (3)
N3—C6—H6B	108.8	C16—C17—H17	119.9
C5—C6—H6B	108.8	C12—C17—H17	119.9
H6A—C6—H6B	107.7	C8—N1—C1	126.6 (3)
C2—C7—N3	123.2 (3)	C8—N1—H1A	113 (2)
C2—C7—N2	121.8 (3)	C1—N1—H1A	119 (2)
N3—C7—N2	115.0 (3)	C8—N2—C7	120.9 (3)
O2—C8—N1	121.3 (3)	C8—N2—C9	117.1 (3)
O2—C8—N2	122.8 (3)	C7—N2—C9	120.2 (3)
N1—C8—N2	115.9 (3)	C7—N3—C12	120.0 (2)
O3—C9—N2	105.8 (3)	C7—N3—C6	119.6 (3)
O3—C9—H9A	110.6	C12—N3—C6	120.0 (3)
N2—C9—H9A	110.6	C2—N4—C4	122.3 (3)
O3—C9—H9B	110.6	C2—N4—C3	120.2 (3)
N2—C9—H9B	110.6	C4—N4—C3	117.1 (3)
H9A—C9—H9B	108.7	C10—O3—C9	117.7 (4)
O3—C10—C11	118.3 (5)
O1—C1—C2—C7	176.9 (3)	N1—C8—N2—C9	165.3 (3)
N1—C1—C2—C7	−5.3 (4)	C2—C7—N2—C8	3.3 (5)
O1—C1—C2—N4	−2.4 (5)	N3—C7—N2—C8	−177.8 (3)
N1—C1—C2—N4	175.4 (3)	C2—C7—N2—C9	−161.2 (3)
N4—C4—C5—C6	63.4 (5)	N3—C7—N2—C9	17.8 (4)
C4—C5—C6—N3	−56.3 (5)	O3—C9—N2—C8	−93.3 (3)
N4—C2—C7—N3	−0.1 (5)	O3—C9—N2—C7	71.8 (4)
C1—C2—C7—N3	−179.5 (3)	C2—C7—N3—C12	−112.7 (4)
N4—C2—C7—N2	178.7 (3)	N2—C7—N3—C12	68.4 (4)
C1—C2—C7—N2	−0.6 (5)	C2—C7—N3—C6	60.4 (5)
C17—C12—C13—C14	1.1 (5)	N2—C7—N3—C6	−118.5 (4)
N3—C12—C13—C14	−177.8 (3)	C13—C12—N3—C7	−156.5 (3)
C12—C13—C14—C15	−1.5 (5)	C17—C12—N3—C7	24.5 (4)
C13—C14—C15—C16	1.2 (6)	C13—C12—N3—C6	30.4 (5)
C14—C15—C16—C17	−0.5 (6)	C17—C12—N3—C6	−148.6 (4)
C15—C16—C17—C12	0.2 (5)	C5—C6—N3—C7	−23.0 (6)
C13—C12—C17—C16	−0.5 (5)	C5—C6—N3—C12	150.2 (4)
N3—C12—C17—C16	178.4 (3)	C7—C2—N4—C4	−55.7 (5)
O2—C8—N1—C1	173.7 (3)	C1—C2—N4—C4	123.6 (4)
N2—C8—N1—C1	−7.3 (5)	C7—C2—N4—C3	132.0 (4)
O1—C1—N1—C8	−172.3 (3)	C1—C2—N4—C3	−48.7 (5)
C2—C1—N1—C8	9.8 (5)	C5—C4—N4—C2	13.9 (6)
O2—C8—N2—C7	179.3 (3)	C5—C4—N4—C3	−173.6 (4)
N1—C8—N2—C7	0.4 (4)	C11—C10—O3—C9	−179.7 (5)
O2—C8—N2—C9	−15.7 (5)	N2—C9—O3—C10	−179.3 (4)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1A···O2i	0.95 (4)	1.91 (4)	2.862 (4)	175 (3)
C13—H13···O1ii	0.93	2.49	3.397 (5)	164

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1A⋯O2i	0.95 (4)	1.91 (4)	2.862 (4)	175 (3)
C13—H13⋯O1ii	0.93	2.49	3.397 (5)	164

Symmetry codes: (i) ; (ii) .