Ethyl 2-diethyl­amino-4-oxo-3,5-diphenyl-4,5-dihydro-3H-pyrrolo­[3,2-d]pyrimidine-7-carboxyl­ate

Gao, H.-T.; Li, L.; Ye, F.; Hu, Y.-G.

doi:10.1107/S1600536811052883

organic compounds

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ISSN: 2056-9890

Volume 68| Part 1| January 2012| Page o118

doi:10.1107/S1600536811052883

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Ethyl 2-diethylamino-4-oxo-3,5-diphenyl-4,5-dihydro-3H-pyrrolo[3,2-d]pyrimidine-7-carboxylate

Hai-Tao Gao,^a Li Li,^b Fang Ye ^c ^* and Yang-Gen Hu ^c,^a ^*

^aInstitute of Medicinal Chemistry, Hubei University of Medicine, Shiyan 442000, People's Republic of China, ^bThe Library of Hubei University of Medicine, Shiyan 442000, People's Republic of China, and ^cDepartment of Pharmacy, Taihe Hospital of Hubei University of Medicine, Shiyan 442000, People's Republic of China
^*Correspondence e-mail: , huyangg111@yahoo.com.cn

(Received 12 November 2011; accepted 8 December 2011; online 14 December 2011)

In the title compound, C₂₅H₂₆N₄O₃, the two fused pyrrolo[3,2-d]pyrimidine rings form a dihedral angle of 3.7 (2)°. The two substituent phenyl rings are twisted with respect to the pyrrole and pyrimidine rings, making dihedral angles of 57.2 (2) and 69.0 (2)°, respectively. The ethyl and ethoxy groups are disordered over two positions; the site occupancies are 0.53 (1) and 0.47 (1) for ethyl, and 0.63 (1) and 0.37 (1) for ethoxy. The crystal packing features C—H⋯O hydrogen bonds.

Related literature

For the synthesis, see: Hu et al. (2006 , 2007 , 2010 ). For related structures, see: He et al. (2007a ,b ); Ma et al. (2009 ); Zeng & Yan (2008 ).

Experimental

Crystal data

C₂₅H₂₆N₄O₃
M_r = 430.50
Monoclinic, C c
a = 19.481 (2) Å
b = 12.0745 (13) Å
c = 10.4393 (11) Å
β = 115.006 (2)°
V = 2225.4 (4) Å³
Z = 4
Mo Kα radiation
μ = 0.09 mm⁻¹
T = 298 K
0.20 × 0.10 × 0.10 mm

Data collection

Bruker SMART 4K CCD area-detector diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2002 ) T_min = 0.973, T_max = 0.991
7050 measured reflections
2192 independent reflections
1846 reflections with I > 2σ(I)
R_int = 0.050

Refinement

R[F² > 2σ(F²)] = 0.046
wR(F²) = 0.104
S = 1.00
2192 reflections
332 parameters
12 restraints
H-atom parameters constrained
Δρ_max = 0.15 e Å⁻³
Δρ_min = −0.19 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C6—H6⋯O1ⁱ	0.93	2.50	3.320 (5)	147
C19—H19B⋯O1ⁱⁱ	0.96	2.59	3.545 (8)	175
C25—H25⋯O2ⁱⁱⁱ	0.93	2.60	3.295 (5)	132
Symmetry codes: (i) $[x, -y+1, z-{\script{1\over 2}}]$ ; (ii) $[x-{\script{1\over 2}}, y-{\script{1\over 2}}, z-1]$ ; (iii) $[x+{\script{1\over 2}}, -y+{\script{1\over 2}}, z+{\script{1\over 2}}]$ .

Data collection: SMART (Bruker, 2002); cell refinement: SAINT (Bruker, 2002); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: PLATON (Spek, 2009); software used to prepare material for publication: SHELXTL (Sheldrick, 2008).

Supporting information

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536811052883/yk2034sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536811052883/yk2034Isup2.hkl

Supporting information file. DOI: 10.1107/S1600536811052883/yk2034Isup3.cml

checkCIF report

Comment top

As a part of our ongoing work in the preparation of derivatives of heterocyclic compounds (Hu et al., 2006, 2007, 2010; He et al., 2007a,b; Ma et al. 2009; Zeng et al., 2008), we have synthesized and structurally characterized the title compound (Fig. 1). In the molecule, the two fused rings of pyrrolo[3,2-d]pyrimidine form a dihedral angle of 3.7 (2)°. The attached two phenyl rings are twisted with respect to the heterocyclic pyrrolo[3,2-d]pyrimidine system, making dihedral angles of 56.8 (2)° and 69.3 (2)°, respectively. The ethyl group (C13—C14) is disordered over two sites with occupancies that refined to 0.53 (1) and 0.47 (1); the ethoxy group (C18—C19) is also disordered over two sites with occupancies 0.63 (1) and 0.37 (1). The crystal packing is stabilized by intermolecular C—H···O hydrogen bonds. There are no π-π interactions.

Related literature top

For the synthesis, see: Hu et al. (2006, 2007, 2010). For related structures, see: He et al. (2007a,b); Ma et al. (2009); Zeng & Yan (2008).

Experimental top

The title compound was obtained in good yield via aza-Wittig reaction. Crystals suitable for single-crystal X-ray diffraction were obtained by recrystallization from a mixture of ethanol and dichloromethane (1:1 v/v) at room temperature.

Computing details top

Data collection: SMART (Bruker, 2002); cell refinement: SAINT (Bruker, 2002); data reduction: SAINT (Bruker, 2002); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: PLATON (Spek, 2009); software used to prepare material for publication: SHELXTL (Sheldrick, 2008).

Figures top

Fig. 1. The molecular structure of the title compound showing the atom-labeling scheme with displacement ellipsoids drawn at the 30% probability level.

Ethyl 2-diethylamino-4-oxo-3,5-diphenyl-4,5-dihydro-3H- pyrrolo[3,2-d]pyrimidine-7-carboxylate top

Crystal data top

C₂₅H₂₆N₄O₃	F(000) = 912
M_r = 430.50	D_x = 1.285 Mg m⁻³
Monoclinic, Cc	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: C -2yc	Cell parameters from 2386 reflections
a = 19.481 (2) Å	θ = 2.3–23.4°
b = 12.0745 (13) Å	µ = 0.09 mm⁻¹
c = 10.4393 (11) Å	T = 298 K
β = 115.006 (2)°	Block, colourless
V = 2225.4 (4) Å³	0.20 × 0.10 × 0.10 mm
Z = 4

Data collection top

Bruker SMART 4K CCD area-detector diffractometer	2192 independent reflections
Radiation source: fine-focus sealed tube	1846 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.050
ϕ and ω scans	θ_max = 26.0°, θ_min = 2.0°
Absorption correction: multi-scan (SADABS; Bruker, 2002)	h = −24→24
T_min = 0.973, T_max = 0.991	k = −14→14
7050 measured reflections	l = −10→12

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)] = 0.046	H-atom parameters constrained
wR(F²) = 0.104	w = 1/[σ²(F_o²) + (0.063P)²] where P = (F_o² + 2F_c²)/3
S = 1.00	(Δ/σ)_max < 0.001
2192 reflections	Δρ_max = 0.15 e Å⁻³
332 parameters	Δρ_min = −0.19 e Å⁻³
12 restraints	Absolute structure: no
Primary atom site location: structure-invariant direct methods

Crystal data top

C₂₅H₂₆N₄O₃	V = 2225.4 (4) Å³
M_r = 430.50	Z = 4
Monoclinic, Cc	Mo Kα radiation
a = 19.481 (2) Å	µ = 0.09 mm⁻¹
b = 12.0745 (13) Å	T = 298 K
c = 10.4393 (11) Å	0.20 × 0.10 × 0.10 mm
β = 115.006 (2)°

Data collection top

Bruker SMART 4K CCD area-detector diffractometer	2192 independent reflections
Absorption correction: multi-scan (SADABS; Bruker, 2002)	1846 reflections with I > 2σ(I)
T_min = 0.973, T_max = 0.991	R_int = 0.050
7050 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.046	12 restraints
wR(F²) = 0.104	H-atom parameters constrained
S = 1.00	Δρ_max = 0.15 e Å⁻³
2192 reflections	Δρ_min = −0.19 e Å⁻³
332 parameters	Absolute structure: no

Special details top

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.

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

	x	y	z	U_iso*/U_eq	Occ. (<1)
C1	0.35411 (19)	0.5896 (2)	0.3254 (4)	0.0403 (7)
C2	0.3739 (3)	0.6278 (3)	0.4599 (4)	0.0603 (10)
H2	0.3554	0.5935	0.5188	0.072*
C3	0.4218 (3)	0.7183 (4)	0.5069 (5)	0.0839 (15)
H3	0.4357	0.7452	0.5980	0.101*
C4	0.4489 (3)	0.7682 (3)	0.4199 (7)	0.0839 (15)
H4	0.4802	0.8300	0.4513	0.101*
C5	0.4306 (2)	0.7280 (3)	0.2885 (6)	0.0697 (13)
H5	0.4500	0.7615	0.2306	0.084*
C6	0.3834 (2)	0.6381 (3)	0.2401 (4)	0.0489 (8)
H6	0.3713	0.6102	0.1501	0.059*
C7	0.33929 (19)	0.3910 (3)	0.3331 (3)	0.0401 (8)
C8	0.23552 (19)	0.5019 (3)	0.1557 (4)	0.0481 (8)
C9	0.29509 (19)	0.3005 (2)	0.2527 (3)	0.0398 (7)
C10	0.22868 (18)	0.3156 (3)	0.1325 (3)	0.0415 (7)
C11	0.1974 (3)	0.6797 (3)	0.2194 (6)	0.0808 (14)
H11A	0.2229	0.6464	0.3122	0.097*
H11B	0.1438	0.6830	0.1972	0.097*
C12	0.2268 (3)	0.7972 (3)	0.2256 (6)	0.0738 (12)
H12A	0.2789	0.7949	0.2407	0.111*
H12B	0.2225	0.8365	0.3019	0.111*
H12C	0.1974	0.8343	0.1381	0.111*
C13	0.1572 (6)	0.6089 (8)	−0.0445 (10)	0.063 (3)	0.53
H13A	0.1804	0.5621	−0.0907	0.075*	0.53
H13B	0.1085	0.5767	−0.0613	0.075*	0.53
C14	0.1442 (5)	0.7208 (7)	−0.1108 (8)	0.071 (2)	0.53
H14A	0.1194	0.7671	−0.0686	0.107*	0.53
H14B	0.1130	0.7143	−0.2103	0.107*	0.53
H14C	0.1920	0.7532	−0.0962	0.107*	0.53
C13'	0.1387 (5)	0.6277 (11)	−0.0102 (11)	0.060 (4)	0.47
H13C	0.1144	0.6960	−0.0032	0.072*	0.47
H13D	0.1033	0.5668	−0.0282	0.072*	0.47
C14'	0.1678 (6)	0.6352 (11)	−0.1238 (9)	0.080 (3)	0.47
H14D	0.2101	0.6851	−0.0936	0.120*	0.47
H14E	0.1283	0.6622	−0.2098	0.120*	0.47
H14F	0.1835	0.5632	−0.1398	0.120*	0.47
C15	0.19836 (18)	0.2084 (3)	0.0816 (4)	0.0438 (8)
C16	0.2478 (2)	0.1342 (3)	0.1758 (4)	0.0460 (8)
H16	0.2418	0.0577	0.1696	0.055*
C17	0.1284 (2)	0.1791 (3)	−0.0417 (4)	0.0497 (8)
C18	0.0502 (6)	0.0198 (12)	−0.1557 (11)	0.066 (4)	0.63
H18A	0.0079	0.0694	−0.1744	0.079*	0.63
H18B	0.0403	−0.0499	−0.1203	0.079*	0.63
C19	0.0625 (5)	0.0017 (8)	−0.2874 (9)	0.069 (2)	0.63
H19A	0.0705	0.0718	−0.3224	0.103*	0.63
H19B	0.0187	−0.0336	−0.3581	0.103*	0.63
H19C	0.1061	−0.0445	−0.2656	0.103*	0.63
C18'	0.0571 (10)	0.0377 (18)	−0.1873 (18)	0.066 (7)	0.37
H18C	0.0465	0.0971	−0.2556	0.079*	0.37
H18D	0.0122	0.0258	−0.1708	0.079*	0.37
C19'	0.0759 (11)	−0.0666 (16)	−0.245 (2)	0.097 (5)	0.37
H19D	0.1168	−0.0523	−0.2708	0.146*	0.37
H19E	0.0322	−0.0906	−0.3266	0.146*	0.37
H19F	0.0906	−0.1234	−0.1739	0.146*	0.37
C20	0.3654 (2)	0.1325 (2)	0.3965 (3)	0.0411 (7)
C21	0.3453 (2)	0.0630 (3)	0.4797 (4)	0.0541 (9)
H21	0.2946	0.0540	0.4616	0.065*
C22	0.4006 (3)	0.0071 (3)	0.5897 (5)	0.0684 (12)
H22	0.3872	−0.0402	0.6457	0.082*
C23	0.4755 (3)	0.0207 (3)	0.6173 (4)	0.0635 (11)
H23	0.5129	−0.0167	0.6924	0.076*
C24	0.4952 (2)	0.0900 (3)	0.5332 (4)	0.0558 (9)
H24	0.5459	0.0984	0.5508	0.067*
C25	0.4401 (2)	0.1468 (3)	0.4232 (4)	0.0477 (8)
H25	0.4535	0.1945	0.3676	0.057*
N1	0.30567 (16)	0.4938 (2)	0.2734 (3)	0.0427 (6)
N2	0.19752 (16)	0.4179 (2)	0.0831 (3)	0.0499 (7)
N3	0.20773 (19)	0.6083 (2)	0.1163 (4)	0.0717 (11)
N4	0.30646 (16)	0.18742 (19)	0.2789 (3)	0.0411 (6)
O1	0.39918 (14)	0.38737 (18)	0.4370 (3)	0.0535 (6)
O2	0.08390 (15)	0.2436 (2)	−0.1197 (3)	0.0663 (8)
O3	0.12107 (15)	0.0691 (2)	−0.0540 (3)	0.0713 (8)

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
C1	0.0400 (17)	0.0294 (14)	0.0459 (19)	−0.0009 (13)	0.0126 (15)	−0.0004 (13)
C2	0.086 (3)	0.0422 (18)	0.049 (2)	−0.0030 (18)	0.024 (2)	−0.0038 (17)
C3	0.107 (4)	0.051 (2)	0.060 (3)	−0.002 (3)	0.002 (3)	−0.019 (2)
C4	0.062 (3)	0.046 (2)	0.117 (4)	−0.018 (2)	0.012 (3)	−0.015 (3)
C5	0.054 (2)	0.0420 (19)	0.116 (4)	0.0014 (18)	0.039 (3)	0.015 (2)
C6	0.050 (2)	0.0412 (17)	0.059 (2)	0.0023 (15)	0.0267 (18)	0.0026 (15)
C7	0.0405 (19)	0.0384 (16)	0.0391 (19)	−0.0017 (13)	0.0146 (17)	0.0007 (13)
C8	0.041 (2)	0.0399 (18)	0.054 (2)	−0.0010 (15)	0.0115 (18)	0.0056 (15)
C9	0.0412 (18)	0.0346 (15)	0.0420 (18)	−0.0043 (14)	0.0159 (15)	−0.0034 (13)
C10	0.0368 (18)	0.0405 (16)	0.0429 (18)	−0.0054 (14)	0.0126 (15)	−0.0032 (14)
C11	0.060 (3)	0.048 (2)	0.141 (5)	0.0094 (19)	0.048 (3)	0.006 (3)
C12	0.071 (3)	0.047 (2)	0.096 (3)	0.009 (2)	0.028 (2)	−0.005 (2)
C13	0.034 (5)	0.049 (6)	0.082 (9)	0.013 (4)	0.001 (5)	0.011 (5)
C14	0.071 (6)	0.067 (5)	0.067 (5)	0.005 (4)	0.020 (5)	0.002 (4)
C13'	0.027 (6)	0.044 (5)	0.094 (8)	0.010 (4)	0.012 (5)	0.005 (5)
C14'	0.076 (7)	0.095 (9)	0.057 (7)	0.012 (6)	0.017 (6)	0.010 (6)
C15	0.0385 (19)	0.0446 (18)	0.0441 (19)	−0.0059 (14)	0.0136 (15)	−0.0065 (15)
C16	0.0461 (19)	0.0362 (16)	0.053 (2)	−0.0108 (15)	0.0184 (16)	−0.0120 (15)
C17	0.037 (2)	0.055 (2)	0.054 (2)	−0.0072 (17)	0.0166 (17)	−0.0114 (18)
C18	0.050 (5)	0.067 (6)	0.071 (6)	−0.028 (4)	0.018 (5)	−0.018 (5)
C19	0.050 (4)	0.074 (5)	0.062 (5)	−0.006 (4)	0.004 (4)	−0.008 (4)
C18'	0.050 (9)	0.067 (11)	0.071 (12)	−0.028 (8)	0.018 (9)	−0.018 (9)
C19'	0.091 (12)	0.102 (13)	0.085 (12)	−0.015 (11)	0.024 (10)	−0.028 (10)
C20	0.0461 (19)	0.0305 (15)	0.0409 (18)	−0.0023 (14)	0.0129 (15)	−0.0044 (13)
C21	0.055 (2)	0.0455 (18)	0.063 (2)	−0.0034 (17)	0.0259 (19)	0.0050 (18)
C22	0.081 (3)	0.053 (2)	0.069 (3)	−0.001 (2)	0.029 (2)	0.017 (2)
C23	0.066 (3)	0.047 (2)	0.057 (2)	0.0078 (18)	0.007 (2)	0.0025 (18)
C24	0.044 (2)	0.051 (2)	0.061 (2)	0.0010 (16)	0.0110 (18)	−0.0144 (18)
C25	0.047 (2)	0.0423 (17)	0.049 (2)	−0.0041 (15)	0.0159 (17)	−0.0048 (15)
N1	0.0402 (15)	0.0330 (13)	0.0479 (16)	−0.0051 (12)	0.0118 (13)	−0.0016 (12)
N2	0.0387 (16)	0.0438 (16)	0.0527 (17)	−0.0048 (12)	0.0054 (14)	0.0019 (13)
N3	0.049 (2)	0.0425 (17)	0.089 (3)	0.0028 (14)	−0.0042 (19)	0.0060 (17)
N4	0.0415 (15)	0.0316 (12)	0.0454 (15)	−0.0047 (12)	0.0139 (13)	−0.0031 (12)
O1	0.0523 (15)	0.0408 (12)	0.0467 (14)	−0.0044 (11)	0.0007 (13)	−0.0021 (10)
O2	0.0453 (15)	0.0629 (16)	0.0679 (18)	0.0027 (13)	0.0018 (14)	−0.0078 (13)
O3	0.0526 (17)	0.0558 (15)	0.0760 (19)	−0.0153 (13)	−0.0016 (14)	−0.0192 (15)

Geometric parameters (Å, º) top

C1—C2	1.370 (5)	C13'—H13C	0.9700
C1—C6	1.375 (5)	C13'—H13D	0.9700
C1—N1	1.446 (4)	C14'—H14D	0.9600
C2—C3	1.386 (6)	C14'—H14E	0.9600
C2—H2	0.9300	C14'—H14F	0.9600
C3—C4	1.369 (8)	C15—C16	1.378 (5)
C3—H3	0.9300	C15—C17	1.469 (5)
C4—C5	1.353 (7)	C16—N4	1.355 (4)
C4—H4	0.9300	C16—H16	0.9300
C5—C6	1.374 (5)	C17—O2	1.194 (5)
C5—H5	0.9300	C17—O3	1.336 (4)
C6—H6	0.9300	C18—O3	1.466 (8)
C7—O1	1.212 (4)	C18—C19	1.509 (10)
C7—N1	1.419 (4)	C18—H18A	0.9700
C7—C9	1.424 (4)	C18—H18B	0.9700
C8—N2	1.295 (4)	C19—H19A	0.9600
C8—N3	1.387 (4)	C19—H19B	0.9600
C8—N1	1.402 (4)	C19—H19C	0.9600
C9—C10	1.382 (5)	C18'—O3	1.472 (11)
C9—N4	1.392 (4)	C18'—C19'	1.505 (11)
C10—N2	1.377 (4)	C18'—H18C	0.9700
C10—C15	1.429 (5)	C18'—H18D	0.9700
C11—N3	1.458 (6)	C19'—H19D	0.9600
C11—C12	1.521 (6)	C19'—H19E	0.9600
C11—H11A	0.9700	C19'—H19F	0.9600
C11—H11B	0.9700	C20—C25	1.373 (5)
C12—H12A	0.9600	C20—C21	1.378 (5)
C12—H12B	0.9600	C20—N4	1.440 (4)
C12—H12C	0.9600	C21—C22	1.374 (6)
C13—C14	1.490 (9)	C21—H21	0.9300
C13—N3	1.546 (9)	C22—C23	1.373 (6)
C13—H13A	0.9700	C22—H22	0.9300
C13—H13B	0.9700	C23—C24	1.378 (6)
C14—H14A	0.9600	C23—H23	0.9300
C14—H14B	0.9600	C24—C25	1.378 (5)
C14—H14C	0.9600	C24—H24	0.9300
C13'—N3	1.451 (9)	C25—H25	0.9300
C13'—C14'	1.518 (10)

C2—C1—C6	120.5 (3)	C16—C15—C17	125.4 (3)
C2—C1—N1	120.7 (3)	C10—C15—C17	129.0 (3)
C6—C1—N1	118.7 (3)	N4—C16—C15	111.0 (3)
C1—C2—C3	118.9 (4)	N4—C16—H16	124.5
C1—C2—H2	120.5	C15—C16—H16	124.5
C3—C2—H2	120.5	O2—C17—O3	124.5 (3)
C4—C3—C2	120.3 (4)	O2—C17—C15	125.3 (3)
C4—C3—H3	119.9	O3—C17—C15	110.2 (3)
C2—C3—H3	119.9	O3—C18—C19	104.8 (8)
C5—C4—C3	120.3 (4)	O3—C18—H18A	110.8
C5—C4—H4	119.9	C19—C18—H18A	110.8
C3—C4—H4	119.9	O3—C18—H18B	110.8
C4—C5—C6	120.4 (4)	C19—C18—H18B	110.8
C4—C5—H5	119.8	H18A—C18—H18B	108.9
C6—C5—H5	119.8	O3—C18'—C19'	110.0 (13)
C5—C6—C1	119.6 (4)	O3—C18'—H18C	109.7
C5—C6—H6	120.2	C19'—C18'—H18C	109.7
C1—C6—H6	120.2	O3—C18'—H18D	109.7
O1—C7—N1	121.0 (3)	C19'—C18'—H18D	109.7
O1—C7—C9	127.8 (3)	H18C—C18'—H18D	108.2
N1—C7—C9	111.1 (3)	C18'—C19'—H19D	109.5
N2—C8—N3	119.8 (3)	C18'—C19'—H19E	109.5
N2—C8—N1	124.2 (3)	H19D—C19'—H19E	109.5
N3—C8—N1	116.0 (3)	C18'—C19'—H19F	109.5
C10—C9—N4	108.5 (3)	H19D—C19'—H19F	109.5
C10—C9—C7	122.3 (3)	H19E—C19'—H19F	109.5
N4—C9—C7	129.1 (3)	C25—C20—C21	120.5 (3)
N2—C10—C9	123.6 (3)	C25—C20—N4	120.7 (3)
N2—C10—C15	128.8 (3)	C21—C20—N4	118.8 (3)
C9—C10—C15	107.4 (3)	C22—C21—C20	119.7 (4)
N3—C11—C12	114.6 (4)	C22—C21—H21	120.2
N3—C11—H11A	108.6	C20—C21—H21	120.2
C12—C11—H11A	108.6	C23—C22—C21	120.3 (4)
N3—C11—H11B	108.6	C23—C22—H22	119.8
C12—C11—H11B	108.6	C21—C22—H22	119.8
H11A—C11—H11B	107.6	C22—C23—C24	119.7 (4)
C11—C12—H12A	109.5	C22—C23—H23	120.1
C11—C12—H12B	109.5	C24—C23—H23	120.1
H12A—C12—H12B	109.5	C25—C24—C23	120.3 (4)
C11—C12—H12C	109.5	C25—C24—H24	119.9
H12A—C12—H12C	109.5	C23—C24—H24	119.9
H12B—C12—H12C	109.5	C20—C25—C24	119.5 (3)
C14—C13—N3	114.5 (7)	C20—C25—H25	120.2
C14—C13—H13A	108.6	C24—C25—H25	120.2
N3—C13—H13A	108.6	C8—N1—C7	122.9 (2)
C14—C13—H13B	108.6	C8—N1—C1	120.9 (3)
N3—C13—H13B	108.6	C7—N1—C1	115.3 (3)
H13A—C13—H13B	107.6	C8—N2—C10	115.6 (3)
N3—C13'—C14'	102.3 (7)	C8—N3—C13'	121.0 (6)
N3—C13'—H13C	111.3	C8—N3—C11	119.2 (4)
C14'—C13'—H13C	111.3	C13'—N3—C11	102.3 (6)
N3—C13'—H13D	111.3	C8—N3—C13	108.4 (4)
C14'—C13'—H13D	111.3	C13'—N3—C13	24.6 (4)
H13C—C13'—H13D	109.2	C11—N3—C13	125.1 (5)
C13'—C14'—H14D	109.5	C16—N4—C9	107.4 (3)
C13'—C14'—H14E	109.5	C16—N4—C20	124.0 (2)
H14D—C14'—H14E	109.5	C9—N4—C20	128.5 (3)
C13'—C14'—H14F	109.5	C17—O3—C18	120.2 (7)
H14D—C14'—H14F	109.5	C17—O3—C18'	111.1 (9)
H14E—C14'—H14F	109.5	C18—O3—C18'	18.0 (13)
C16—C15—C10	105.6 (3)

C6—C1—C2—C3	2.1 (6)	C2—C1—N1—C8	119.2 (4)
N1—C1—C2—C3	178.5 (4)	C6—C1—N1—C8	−64.3 (4)
C1—C2—C3—C4	−0.1 (7)	C2—C1—N1—C7	−71.1 (4)
C2—C3—C4—C5	−1.5 (8)	C6—C1—N1—C7	105.4 (3)
C3—C4—C5—C6	1.2 (7)	N3—C8—N2—C10	−178.4 (3)
C4—C5—C6—C1	0.7 (6)	N1—C8—N2—C10	2.9 (5)
C2—C1—C6—C5	−2.4 (5)	C9—C10—N2—C8	1.3 (5)
N1—C1—C6—C5	−178.9 (3)	C15—C10—N2—C8	175.7 (3)
O1—C7—C9—C10	−177.6 (3)	N2—C8—N3—C13'	−3.7 (8)
N1—C7—C9—C10	0.3 (4)	N1—C8—N3—C13'	175.1 (6)
O1—C7—C9—N4	5.3 (6)	N2—C8—N3—C11	124.5 (4)
N1—C7—C9—N4	−176.9 (3)	N1—C8—N3—C11	−56.7 (5)
N4—C9—C10—N2	174.7 (3)	N2—C8—N3—C13	−27.1 (7)
C7—C9—C10—N2	−3.0 (5)	N1—C8—N3—C13	151.7 (6)
N4—C9—C10—C15	−0.7 (3)	C14'—C13'—N3—C8	−86.6 (10)
C7—C9—C10—C15	−178.3 (3)	C14'—C13'—N3—C11	138.0 (8)
N2—C10—C15—C16	−174.1 (3)	C14'—C13'—N3—C13	−21.7 (15)
C9—C10—C15—C16	0.9 (4)	C12—C11—N3—C8	134.4 (4)
N2—C10—C15—C17	4.2 (6)	C12—C11—N3—C13'	−89.2 (7)
C9—C10—C15—C17	179.2 (3)	C12—C11—N3—C13	−79.0 (8)
C10—C15—C16—N4	−0.9 (4)	C14—C13—N3—C8	−160.6 (8)
C17—C15—C16—N4	−179.3 (3)	C14—C13—N3—C13'	74.4 (19)
C16—C15—C17—O2	176.5 (4)	C14—C13—N3—C11	49.9 (12)
C10—C15—C17—O2	−1.4 (6)	C15—C16—N4—C9	0.5 (4)
C16—C15—C17—O3	−3.0 (5)	C15—C16—N4—C20	176.8 (3)
C10—C15—C17—O3	179.0 (3)	C10—C9—N4—C16	0.1 (4)
C25—C20—C21—C22	−0.5 (5)	C7—C9—N4—C16	177.6 (3)
N4—C20—C21—C22	177.9 (3)	C10—C9—N4—C20	−175.9 (3)
C20—C21—C22—C23	0.4 (6)	C7—C9—N4—C20	1.5 (6)
C21—C22—C23—C24	−0.7 (6)	C25—C20—N4—C16	124.3 (3)
C22—C23—C24—C25	1.0 (6)	C21—C20—N4—C16	−54.1 (5)
C21—C20—C25—C24	0.8 (5)	C25—C20—N4—C9	−60.2 (5)
N4—C20—C25—C24	−177.5 (3)	C21—C20—N4—C9	121.4 (4)
C23—C24—C25—C20	−1.1 (5)	O2—C17—O3—C18	−9.1 (8)
N2—C8—N1—C7	−5.8 (5)	C15—C17—O3—C18	170.5 (6)
N3—C8—N1—C7	175.4 (3)	O2—C17—O3—C18'	8.2 (12)
N2—C8—N1—C1	163.1 (3)	C15—C17—O3—C18'	−172.2 (11)
N3—C8—N1—C1	−15.6 (5)	C19—C18—O3—C17	93.6 (10)
O1—C7—N1—C8	−178.2 (3)	C19—C18—O3—C18'	30 (3)
C9—C7—N1—C8	3.8 (4)	C19'—C18'—O3—C17	144.4 (15)
O1—C7—N1—C1	12.3 (4)	C19'—C18'—O3—C18	−92 (4)
C9—C7—N1—C1	−165.7 (3)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C6—H6···O1ⁱ	0.93	2.50	3.320 (5)	147
C19—H19B···O1ⁱⁱ	0.96	2.59	3.545 (8)	175
C25—H25···O2ⁱⁱⁱ	0.93	2.60	3.295 (5)	132

Symmetry codes: (i) x, −y+1, z−1/2; (ii) x−1/2, y−1/2, z−1; (iii) x+1/2, −y+1/2, z+1/2.

Experimental details

Crystal data
Chemical formula	C₂₅H₂₆N₄O₃
M_r	430.50
Crystal system, space group	Monoclinic, Cc
Temperature (K)	298
a, b, c (Å)	19.481 (2), 12.0745 (13), 10.4393 (11)
β (°)	115.006 (2)
V (Å³)	2225.4 (4)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.09
Crystal size (mm)	0.20 × 0.10 × 0.10

Data collection
Diffractometer	Bruker SMART 4K CCD area-detector diffractometer
Absorption correction	Multi-scan (SADABS; Bruker, 2002)
T_min, T_max	0.973, 0.991
No. of measured, independent and observed [I > 2σ(I)] reflections	7050, 2192, 1846
R_int	0.050
(sin θ/λ)_max (Å⁻¹)	0.617

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.046, 0.104, 1.00
No. of reflections	2192
No. of parameters	332
No. of restraints	12
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.15, −0.19
Absolute structure	No

Computer programs: SMART (Bruker, 2002), SAINT (Bruker, 2002), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), PLATON (Spek, 2009), SHELXTL (Sheldrick, 2008).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C6—H6···O1ⁱ	0.93	2.50	3.320 (5)	146.7
C19—H19B···O1ⁱⁱ	0.96	2.59	3.545 (8)	174.7
C25—H25···O2ⁱⁱⁱ	0.93	2.60	3.295 (5)	132.2

Symmetry codes: (i) x, −y+1, z−1/2; (ii) x−1/2, y−1/2, z−1; (iii) x+1/2, −y+1/2, z+1/2.

Acknowledgements

We gratefully acknowledge financial support of this work by the Science Research Project of Hubei University of Medicine (Nos. 2008CXG01 and 2009QDJ15).

References

Bruker (2002). SMART, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
He, P., Peng, X.-M. & Li, G.-H. (2007a). Acta Cryst. E63, o4884. Web of Science CSD CrossRef IUCr Journals Google Scholar
He, P., Zheng, A., Cai, C.-Q. & Fang, C.-L. (2007b). Acta Cryst. E63, o3185. Web of Science CSD CrossRef IUCr Journals Google Scholar
Hu, Y.-G., Hu, J. & Gao, H.-T. (2007). Acta Cryst. E63, o4735. Web of Science CSD CrossRef IUCr Journals Google Scholar
Hu, Y. G., Wang, Y., Du, S. M., Chen, X. B. & Ding, M. W. (2010). Bioorg. Med. Chem. Lett. 20, 6188–6190. Web of Science CSD CrossRef CAS PubMed Google Scholar
Hu, Y.-G., Zheng, A.-H. & Li, G.-H. (2006). Acta Cryst. E62, o1457–o1459. Web of Science CSD CrossRef IUCr Journals Google Scholar
Ma, J.-K., He, M. & Hu, Y.-G. (2009). Acta Cryst. E65, o2629. Web of Science CSD CrossRef IUCr Journals Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar
Spek, A. L. (2009). Acta Cryst. D65, 148–155. Web of Science CrossRef CAS IUCr Journals Google Scholar
Zeng, G.-P. & Yan, S.-R. (2008). Acta Cryst. E64, o1680. Web of Science CSD CrossRef IUCr Journals Google Scholar

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organic compounds\(\def\hfill{\hskip 5em}\def\hfil{\hskip 3em}\def\eqno#1{\hfil {#1}}\)

Ethyl 2-di­ethyl­amino-4-oxo-3,5-di­phenyl-4,5-di­hydro-3H-pyrrolo­[3,2-d]pyrimidine-7-carboxyl­ate

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Experimental

Crystal data

Data collection

Refinement

Supporting information

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References

organic compounds

Ethyl 2-diethylamino-4-oxo-3,5-diphenyl-4,5-dihydro-3H-pyrrolo[3,2-d]pyrimidine-7-carboxylate