N-(1-Acetyl-5-benzoyl-1,4,5,6-tetra­hydro­pyrrolo­[3,4-c]pyrazol-3-yl)benzamide

Bai, X.-G.; Wang, J.-X.; Wang, Y.-C.

doi:10.1107/S1600536812019708

organic compounds

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ISSN: 2056-9890

Volume 68| Part 6| June 2012| Page o1677

doi:10.1107/S1600536812019708

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N-(1-Acetyl-5-benzoyl-1,4,5,6-tetrahydropyrrolo[3,4-c]pyrazol-3-yl)benzamide

Xiao-Guang Bai,^a Ju-Xian Wang ^a and Yu-Cheng Wang ^a ^*

^aInstitute of Medicinal Biotechnology, Chinese Academy of Medical Sciences and Peking Union Medical College, Beijing 100050, People's Republic of China
^*Correspondence e-mail: hongzhaoupr@yahoo.com

(Received 17 April 2012; accepted 2 May 2012; online 12 May 2012)

In the molecule of the title compound, C₂₁H₁₈N₄O₃, the fused pyrrolo[3,4-c]pyrazole ring system is approximately planar [maximum deviation = 0.0486 (16) Å] and forms dihedral angles of 87.21 (8) and 35.46 (7)° with the phenyl rings. In the crystal, N—H⋯O and C—H⋯O hydrogen bonds and weak C—H⋯π interactions link the molecules into chains parallel to [201].

Related literature

For background to potential anticancer kinase inhibitors, see: Fancelli et al. (2005 ); Gadekar et al. (1968 ). For the structures of related compounds synthesized by our group, see: Guo et al. (2010 ); Xia et al. (2011 ).

Experimental

Crystal data

C₂₁H₁₈N₄O₃
M_r = 374.39
Monoclinic, P 2₁ /c
a = 5.32163 (11) Å
b = 21.1878 (5) Å
c = 16.4585 (3) Å
β = 96.9378 (17)°
V = 1842.16 (7) Å³
Z = 4
Cu Kα radiation
μ = 0.76 mm⁻¹
T = 293 K
0.25 × 0.22 × 0.18 mm

Data collection

Oxford Diffraction Xcalibur Atlas Gemini ultra diffractometer
Absorption correction: multi-scan (CrysAlis PRO; Agilent, 2011 ) T_min = 0.819, T_max = 1.000
10256 measured reflections
3276 independent reflections
2856 reflections with I > 2σ(I)
R_int = 0.018

Refinement

R[F² > 2σ(F²)] = 0.053
wR(F²) = 0.150
S = 1.07
3276 reflections
254 parameters
H-atom parameters constrained
Δρ_max = 0.62 e Å⁻³
Δρ_min = −0.25 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

Cg1 is the centroid of the C16–C21 phenyl ring.

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N4—H4⋯O1ⁱ	0.86	2.23	2.997 (2)	148
C20—H20⋯O1ⁱⁱ	0.93	2.49	3.359 (3)	156
C5—H5A⋯Cg1ⁱⁱ	0.97	2.64	3.508 (3)	150
Symmetry codes: (i) $[x+1, -y+{\script{1\over 2}}, z+{\script{1\over 2}}]$ ; (ii) $[x+2, -y+{\script{1\over 2}}, z+{\script{1\over 2}}]$ .

Data collection: CrysAlis PRO (Agilent, 2011); cell refinement: CrysAlis PRO; data reduction: CrysAlis PRO; 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: SHELXTL.

Supporting information

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536812019708/rz2745sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536812019708/rz2745Isup2.hkl

Supporting information file. DOI: 10.1107/S1600536812019708/rz2745Isup3.cml

checkCIF report

Comment top

In our ongoing project (Guo et al., 2010; Xia et al., 2011) devoted to the development of potential anticancer kinase inhibitors (Fancelli et al., 2005; Gadekar et al., 1968), we have synthesized the title compound and report its crystal structure herein.

In the molecule of the title compound (Fig. 1), bond lengths and angles have normal values. The fused pyrrole-pyrazole ring system is approximately planar (maximum deviation 0.0486 (16) Å for atom N3), the dihedral angle between the two five-membered rings being 1.32 (14)°. The phenyl rings C9–C14 and C16–C21 form dihedral angles of 87.21 (8) and 35.46 (7)°, respectively, with the mean plane through C1/N1/N2/C3/C2/C4/N3/C5. In the crystal structure (Fig. 2), molecules are linked by intermolecular N—H···O and C—H···O hydrogen bonds (Table 1) and by weak C—H···π interactions to form chains running parallel to the [2 0 1] direction.

Related literature top

For background to potential anticancer kinase inhibitors, see: Fancelli et al. (2005); Gadekar et al. (1968). For the structures of related compounds synthesized by our group, see: Guo et al. (2010); Xia et al. (2011).

Experimental top

A solution of benzoyl chloride (3.37 g, 24 mmol) in THF (20 ml) was added slowly to a mixture of 5-tert-butyl 1-ethyl 3-aminopyrrolo[3,4-c]pyrazole-1,5(4H,6H)-dicarboxylate (6.5 g, 21.8 mmol) and DIEA (N,N-diisopropylethylamine; 24 ml, 130.8 mmol) in THF (250 ml) at 0–5 °C for 12 h, the resulting suspension was evaporated under vacuum to dryness, and the residual was taken up with AcOEt and water, the organic layer was separated and stayed for 2 h to form white solid in the solution, separated by filtration and washed with Et2O, to give 7.37 g (84.5%) of 5-tert-butyl 1-ethyl 3-benzamidopyrrolo[3,4-c]pyrazole-1,5(4H,6H)-dicarboxylate as a white solid. A suspension of 5-tert-butyl 1-ethyl 3-benzamidopyrrolo[3,4-c]pyrazole-1,5(4H,6H)-dicarboxylate (7.6 g, 19 mmol) in DCM (300 ml) was pumped dried hydrochloride gas under room temperature for 3 h, filtered, extensively washed with Et2O, and dried under vacuum at 40 °C to give 6.37 g (100%) of ethyl 3-benzamido-5,6-dihydropyrrolo[3,4-c]pyrazole-1(4H)-carboxylate hydrochloride as white powder. A solution of benzoyl chloride (3.04 g, 21.6 mmol) in THF (20 ml) was added slowly to a suspension of ethyl 3-benzamido-5,6-dihydropyrrolo[3,4-c]pyrazole-1(4H)-carboxylate hydrochloride (6.05 g, 18 mmol) and DIEA (17.8 ml, 108 mmol) in THF (200 ml) at 0–5 °C, The resulting suspension was evaporated under vacuum to dryness, and the residual was taken up with AcOEt and water, the organic layer was separated and stayed for 2 h to form white solid in the solution, separated by filtration and washed with Et2O, to give 7.1 g (97.6%) of ethyl 3-benzamido-5-benzoyl-5,6-dihydropyrrolo[3,4-c]pyrazole-1(4H)-carboxylate as a white solid. A solution of ethyl 3-benzamido-5-benzoyl-5,6-dihydropyrrolo[3,4-c]pyrazole-1(4H)-carboxylate (6.8 g, 16.8 mmol) in MeOH (300 ml) and Et3N (30 ml) was stirred at room temperature for 2 h. The resulting mixture was evaporated to dryness and dried under vacuum to give 5.47 g (98%) of N-(5-benzoyl-1,4,5,6-tetrahydropyrrolo[3,4-c]pyrazol-3-yl)benzamide as white powder. A solution of acetyl chloride (0.424 g, 5.4 mmol) in THF (10 ml) was added slowly to a mixture of N-(5-benzoyl-1,4,5,6-tetrahydropyrrolo[3,4-c]pyrazol-3-yl)benzamide (1.5 g, 4.5 mmol) and DIEA (4.5 ml, 27 mmol) in THF (80 ml) at 0–5 °C for 12 h, the resulting suspension was evaporated under vacuum to dryness, and the residual was taken up with AcOEt and water, the organic layer was separated and stayed for 2 h to form white solid in the solution, separated by filtration and washed with Et2O, to give 1.5 g (89%) of N-(1-acetyl-5-benzoyl-1,4,5,6-tetrahydropyrrolo[3,4-c]pyrazol-3-yl)benzamide as a white solid. Colourless block crystals suitable for X-ray diffraction were obtained in 6 days by slow envaporation of a mixed solution (1:1 v/v) of dichloromethane and ethyl acetate.

Computing details top

Data collection: CrysAlis PRO (Agilent, 2011); cell refinement: CrysAlis PRO (Agilent, 2011); data reduction: CrysAlis PRO (Agilent, 2011); 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: SHELXTL (Sheldrick, 2008).

Figures top

	Fig. 1. The molecular structure of the title compound, with displacement ellipsoids are drawn at the 30% probability level.
	Fig. 2. Packing diagram of the title compound viewed along the a axis. Hydrogen bonds are shown as dashed lines.

N-(1-Acetyl-5-benzoyl-1,4,5,6-tetrahydropyrrolo[3,4-c]pyrazol-3- yl)benzamide top

Crystal data top

C₂₁H₁₈N₄O₃	F(000) = 784
M_r = 374.39	D_x = 1.350 Mg m⁻³
Monoclinic, P2₁/c	Cu Kα radiation, λ = 1.54184 Å
Hall symbol: -P 2ybc	Cell parameters from 5825 reflections
a = 5.32163 (11) Å	θ = 3.4–66.8°
b = 21.1878 (5) Å	µ = 0.76 mm⁻¹
c = 16.4585 (3) Å	T = 293 K
β = 96.9378 (17)°	Block, colorless
V = 1842.16 (7) Å³	0.25 × 0.22 × 0.18 mm
Z = 4

Data collection top

Oxford Diffraction Xcalibur Atlas Gemini ultra diffractometer	3276 independent reflections
Radiation source: Enhance Ultra (Cu) X-ray Source	2856 reflections with I > 2σ(I)
Mirror monochromator	R_int = 0.018
Detector resolution: 10.4713 pixels mm^-1	θ_max = 66.9°, θ_min = 3.4°
ω scans	h = −6→5
Absorption correction: multi-scan (CrysAlis PRO; Agilent, 2011)	k = −25→23
T_min = 0.819, T_max = 1.000	l = −19→18
10256 measured reflections

Refinement top

Refinement on F²	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F² > 2σ(F²)] = 0.053	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.150	H-atom parameters constrained
S = 1.07	w = 1/[σ²(F_o²) + (0.0752P)² + 0.8604P] where P = (F_o² + 2F_c²)/3
3276 reflections	(Δ/σ)_max < 0.001
254 parameters	Δρ_max = 0.62 e Å⁻³
0 restraints	Δρ_min = −0.25 e Å⁻³

Crystal data top

C₂₁H₁₈N₄O₃	V = 1842.16 (7) Å³
M_r = 374.39	Z = 4
Monoclinic, P2₁/c	Cu Kα radiation
a = 5.32163 (11) Å	µ = 0.76 mm⁻¹
b = 21.1878 (5) Å	T = 293 K
c = 16.4585 (3) Å	0.25 × 0.22 × 0.18 mm
β = 96.9378 (17)°

Data collection top

Oxford Diffraction Xcalibur Atlas Gemini ultra diffractometer	3276 independent reflections
Absorption correction: multi-scan (CrysAlis PRO; Agilent, 2011)	2856 reflections with I > 2σ(I)
T_min = 0.819, T_max = 1.000	R_int = 0.018
10256 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.053	0 restraints
wR(F²) = 0.150	H-atom parameters constrained
S = 1.07	Δρ_max = 0.62 e Å⁻³
3276 reflections	Δρ_min = −0.25 e Å⁻³
254 parameters

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
O1	−0.5691 (3)	0.31747 (7)	0.32789 (9)	0.0590 (4)
N4	0.3203 (3)	0.24185 (8)	0.66211 (9)	0.0422 (4)
H4	0.3904	0.2161	0.6983	0.051*
N3	−0.3129 (3)	0.29957 (8)	0.44421 (10)	0.0421 (4)
N2	0.0354 (3)	0.16211 (8)	0.61696 (10)	0.0481 (4)
N1	−0.1782 (3)	0.15647 (8)	0.56051 (10)	0.0459 (4)
O2	0.3492 (4)	0.33753 (8)	0.60417 (11)	0.0722 (6)
C8	−0.3981 (4)	0.33561 (9)	0.37999 (11)	0.0421 (4)
C3	0.1126 (3)	0.22096 (9)	0.60959 (10)	0.0380 (4)
C1	−0.2243 (4)	0.21181 (9)	0.51951 (11)	0.0387 (4)
O3	−0.5009 (4)	0.10010 (8)	0.49746 (12)	0.0764 (6)
C2	−0.0472 (3)	0.25406 (9)	0.54786 (10)	0.0370 (4)
C5	−0.4179 (4)	0.23584 (9)	0.45428 (11)	0.0413 (4)
H5A	−0.4240	0.2111	0.4045	0.050*
H5B	−0.5850	0.2375	0.4721	0.050*
C4	−0.0927 (4)	0.31603 (9)	0.50527 (12)	0.0449 (5)
H4A	−0.1351	0.3488	0.5425	0.054*
H4B	0.0522	0.3292	0.4790	0.054*
C15	0.4185 (4)	0.30113 (9)	0.65912 (12)	0.0446 (5)
C21	0.8086 (4)	0.27803 (11)	0.75721 (12)	0.0471 (5)
H21	0.8090	0.2366	0.7384	0.057*
C16	0.6190 (4)	0.31905 (9)	0.72611 (11)	0.0425 (4)
C9	−0.2769 (4)	0.39859 (9)	0.37409 (12)	0.0456 (5)
C17	0.6176 (4)	0.38031 (11)	0.75652 (14)	0.0562 (6)
H17	0.4912	0.4083	0.7359	0.067*
C20	0.9981 (4)	0.29859 (13)	0.81639 (14)	0.0600 (6)
H20	1.1283	0.2713	0.8360	0.072*
C6	−0.3162 (5)	0.10024 (11)	0.54676 (15)	0.0661 (7)
C18	0.8033 (5)	0.39953 (12)	0.81712 (16)	0.0663 (7)
H18	0.7987	0.4401	0.8384	0.080*
C19	0.9951 (4)	0.35908 (14)	0.84631 (15)	0.0658 (7)
H19	1.1225	0.3726	0.8862	0.079*
C12	−0.0648 (6)	0.51684 (12)	0.35967 (17)	0.0757 (8)
H12	0.0022	0.5568	0.3531	0.091*
C14	−0.0915 (6)	0.40756 (13)	0.3251 (2)	0.0800 (8)
H14	−0.0371	0.3738	0.2955	0.096*
C10	−0.3456 (8)	0.44917 (14)	0.4169 (2)	0.1090 (14)
H10	−0.4667	0.4440	0.4526	0.131*
C7	−0.2147 (10)	0.04482 (15)	0.5952 (3)	0.144 (2)
H7A	−0.0354	0.0418	0.5933	0.216*
H7B	−0.2955	0.0071	0.5727	0.216*
H7C	−0.2473	0.0496	0.6510	0.216*
C11	−0.2405 (10)	0.50798 (14)	0.4088 (3)	0.1191 (16)
H11	−0.2940	0.5418	0.4383	0.143*
C13	0.0164 (7)	0.46637 (15)	0.3188 (2)	0.0912 (10)
H13	0.1462	0.4716	0.2863	0.109*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
O1	0.0642 (10)	0.0544 (9)	0.0505 (8)	0.0047 (7)	−0.0257 (7)	−0.0032 (7)
N4	0.0440 (9)	0.0414 (9)	0.0372 (8)	−0.0003 (7)	−0.0114 (7)	0.0038 (6)
N3	0.0397 (8)	0.0425 (9)	0.0404 (8)	−0.0025 (6)	−0.0106 (7)	0.0033 (7)
N2	0.0570 (10)	0.0412 (9)	0.0413 (9)	−0.0033 (7)	−0.0135 (7)	0.0027 (7)
N1	0.0542 (10)	0.0384 (9)	0.0410 (9)	−0.0075 (7)	−0.0103 (7)	0.0016 (7)
O2	0.0808 (12)	0.0558 (10)	0.0684 (11)	−0.0185 (8)	−0.0383 (9)	0.0207 (8)
C8	0.0409 (10)	0.0441 (10)	0.0385 (9)	0.0099 (8)	−0.0066 (8)	−0.0028 (8)
C3	0.0415 (10)	0.0392 (10)	0.0312 (9)	0.0001 (8)	−0.0037 (7)	−0.0005 (7)
C1	0.0408 (10)	0.0405 (10)	0.0332 (9)	−0.0033 (8)	−0.0025 (7)	−0.0009 (7)
O3	0.0830 (12)	0.0615 (11)	0.0758 (11)	−0.0270 (9)	−0.0268 (10)	0.0046 (9)
C2	0.0382 (9)	0.0390 (9)	0.0320 (9)	−0.0013 (7)	−0.0032 (7)	0.0001 (7)
C5	0.0388 (10)	0.0436 (10)	0.0393 (10)	−0.0039 (8)	−0.0042 (8)	−0.0007 (8)
C4	0.0438 (10)	0.0424 (10)	0.0439 (10)	−0.0044 (8)	−0.0140 (8)	0.0051 (8)
C15	0.0432 (11)	0.0447 (11)	0.0424 (10)	−0.0015 (8)	−0.0097 (8)	0.0029 (8)
C21	0.0381 (10)	0.0599 (12)	0.0422 (10)	0.0033 (9)	0.0002 (8)	0.0017 (9)
C16	0.0373 (10)	0.0487 (11)	0.0393 (10)	−0.0054 (8)	−0.0039 (8)	0.0027 (8)
C9	0.0526 (11)	0.0414 (10)	0.0387 (10)	0.0096 (8)	−0.0109 (8)	0.0033 (8)
C17	0.0543 (12)	0.0482 (12)	0.0616 (13)	−0.0054 (10)	−0.0119 (10)	0.0011 (10)
C20	0.0346 (11)	0.0916 (18)	0.0508 (12)	0.0024 (11)	−0.0067 (9)	0.0084 (12)
C6	0.0853 (17)	0.0459 (13)	0.0605 (14)	−0.0183 (12)	−0.0185 (13)	0.0035 (10)
C18	0.0727 (16)	0.0577 (14)	0.0636 (14)	−0.0207 (12)	−0.0114 (12)	−0.0061 (11)
C19	0.0480 (13)	0.0912 (19)	0.0534 (13)	−0.0250 (12)	−0.0130 (10)	0.0008 (12)
C12	0.109 (2)	0.0471 (14)	0.0671 (16)	−0.0103 (14)	−0.0054 (15)	0.0079 (12)
C14	0.0849 (19)	0.0602 (16)	0.100 (2)	−0.0115 (13)	0.0312 (17)	−0.0197 (14)
C10	0.171 (4)	0.0469 (15)	0.127 (3)	−0.0042 (18)	0.093 (3)	−0.0123 (16)
C7	0.198 (5)	0.0529 (18)	0.153 (4)	−0.045 (2)	−0.095 (3)	0.036 (2)
C11	0.201 (4)	0.0424 (15)	0.130 (3)	−0.001 (2)	0.085 (3)	−0.0123 (17)
C13	0.101 (2)	0.076 (2)	0.102 (2)	−0.0246 (17)	0.0325 (19)	−0.0060 (17)

Geometric parameters (Å, º) top

O1—C8	1.234 (2)	C21—H21	0.9300
N4—C15	1.364 (3)	C16—C17	1.391 (3)
N4—C3	1.391 (2)	C9—C10	1.357 (3)
N4—H4	0.8600	C9—C14	1.361 (4)
N3—C8	1.338 (2)	C17—C18	1.378 (3)
N3—C5	1.478 (2)	C17—H17	0.9300
N3—C4	1.490 (2)	C20—C19	1.374 (4)
N2—C3	1.323 (2)	C20—H20	0.9300
N2—N1	1.384 (2)	C6—C7	1.484 (4)
N1—C1	1.360 (2)	C18—C19	1.374 (4)
N1—C6	1.403 (3)	C18—H18	0.9300
O2—C15	1.212 (2)	C19—H19	0.9300
C8—C9	1.490 (3)	C12—C11	1.322 (5)
C3—C2	1.428 (2)	C12—C13	1.361 (4)
C1—C2	1.342 (3)	C12—H12	0.9300
C1—C5	1.485 (2)	C14—C13	1.381 (4)
O3—C6	1.197 (3)	C14—H14	0.9300
C2—C4	1.494 (3)	C10—C11	1.379 (5)
C5—H5A	0.9700	C10—H10	0.9300
C5—H5B	0.9700	C7—H7A	0.9600
C4—H4A	0.9700	C7—H7B	0.9600
C4—H4B	0.9700	C7—H7C	0.9600
C15—C16	1.488 (3)	C11—H11	0.9300
C21—C16	1.382 (3)	C13—H13	0.9300
C21—C20	1.385 (3)

C15—N4—C3	123.38 (15)	C21—C16—C15	122.68 (19)
C15—N4—H4	118.3	C17—C16—C15	118.04 (18)
C3—N4—H4	118.3	C10—C9—C14	117.2 (2)
C8—N3—C5	120.87 (15)	C10—C9—C8	121.8 (2)
C8—N3—C4	124.28 (16)	C14—C9—C8	120.9 (2)
C5—N3—C4	114.54 (14)	C18—C17—C16	120.1 (2)
C3—N2—N1	105.01 (15)	C18—C17—H17	119.9
C1—N1—N2	110.03 (15)	C16—C17—H17	119.9
C1—N1—C6	126.34 (17)	C19—C20—C21	120.4 (2)
N2—N1—C6	123.57 (17)	C19—C20—H20	119.8
O1—C8—N3	121.50 (19)	C21—C20—H20	119.8
O1—C8—C9	121.48 (17)	O3—C6—N1	118.8 (2)
N3—C8—C9	117.02 (16)	O3—C6—C7	125.3 (2)
N2—C3—N4	118.38 (16)	N1—C6—C7	115.8 (2)
N2—C3—C2	111.31 (16)	C19—C18—C17	120.4 (2)
N4—C3—C2	130.26 (17)	C19—C18—H18	119.8
C2—C1—N1	109.02 (16)	C17—C18—H18	119.8
C2—C1—C5	114.80 (17)	C20—C19—C18	119.8 (2)
N1—C1—C5	136.18 (17)	C20—C19—H19	120.1
C1—C2—C3	104.63 (16)	C18—C19—H19	120.1
C1—C2—C4	110.84 (16)	C11—C12—C13	118.8 (3)
C3—C2—C4	144.53 (17)	C11—C12—H12	120.6
N3—C5—C1	98.93 (14)	C13—C12—H12	120.6
N3—C5—H5A	112.0	C9—C14—C13	120.5 (3)
C1—C5—H5A	112.0	C9—C14—H14	119.7
N3—C5—H5B	112.0	C13—C14—H14	119.7
C1—C5—H5B	112.0	C9—C10—C11	121.7 (3)
H5A—C5—H5B	109.7	C9—C10—H10	119.1
N3—C4—C2	100.40 (15)	C11—C10—H10	119.1
N3—C4—H4A	111.7	C6—C7—H7A	109.5
C2—C4—H4A	111.7	C6—C7—H7B	109.5
N3—C4—H4B	111.7	H7A—C7—H7B	109.5
C2—C4—H4B	111.7	C6—C7—H7C	109.5
H4A—C4—H4B	109.5	H7A—C7—H7C	109.5
O2—C15—N4	121.98 (17)	H7B—C7—H7C	109.5
O2—C15—C16	121.14 (18)	C12—C11—C10	120.8 (3)
N4—C15—C16	116.88 (16)	C12—C11—H11	119.6
C16—C21—C20	120.0 (2)	C10—C11—H11	119.6
C16—C21—H21	120.0	C12—C13—C14	120.8 (3)
C20—C21—H21	120.0	C12—C13—H13	119.6
C21—C16—C17	119.25 (18)	C14—C13—H13	119.6

C3—N2—N1—C1	0.7 (2)	C3—N4—C15—O2	−8.7 (3)
C3—N2—N1—C6	178.1 (2)	C3—N4—C15—C16	172.23 (17)
C5—N3—C8—O1	1.1 (3)	C20—C21—C16—C17	−1.7 (3)
C4—N3—C8—O1	174.41 (19)	C20—C21—C16—C15	176.36 (19)
C5—N3—C8—C9	−178.70 (17)	O2—C15—C16—C21	−138.6 (2)
C4—N3—C8—C9	−5.4 (3)	N4—C15—C16—C21	40.5 (3)
N1—N2—C3—N4	176.94 (16)	O2—C15—C16—C17	39.5 (3)
N1—N2—C3—C2	−0.7 (2)	N4—C15—C16—C17	−141.4 (2)
C15—N4—C3—N2	178.88 (19)	O1—C8—C9—C10	98.7 (3)
C15—N4—C3—C2	−4.0 (3)	N3—C8—C9—C10	−81.5 (3)
N2—N1—C1—C2	−0.4 (2)	O1—C8—C9—C14	−81.3 (3)
C6—N1—C1—C2	−177.8 (2)	N3—C8—C9—C14	98.5 (3)
N2—N1—C1—C5	−179.4 (2)	C21—C16—C17—C18	−0.2 (3)
C6—N1—C1—C5	3.2 (4)	C15—C16—C17—C18	−178.4 (2)
N1—C1—C2—C3	0.0 (2)	C16—C21—C20—C19	1.9 (3)
C5—C1—C2—C3	179.24 (16)	C1—N1—C6—O3	−4.1 (4)
N1—C1—C2—C4	−179.16 (17)	N2—N1—C6—O3	178.9 (2)
C5—C1—C2—C4	0.1 (2)	C1—N1—C6—C7	175.1 (3)
N2—C3—C2—C1	0.5 (2)	N2—N1—C6—C7	−1.9 (4)
N4—C3—C2—C1	−176.80 (19)	C16—C17—C18—C19	1.9 (4)
N2—C3—C2—C4	179.1 (3)	C21—C20—C19—C18	−0.2 (4)
N4—C3—C2—C4	1.8 (4)	C17—C18—C19—C20	−1.7 (4)
C8—N3—C5—C1	167.03 (17)	C10—C9—C14—C13	−1.2 (5)
C4—N3—C5—C1	−6.9 (2)	C8—C9—C14—C13	178.8 (3)
C2—C1—C5—N3	4.0 (2)	C14—C9—C10—C11	2.7 (6)
N1—C1—C5—N3	−177.0 (2)	C8—C9—C10—C11	−177.3 (4)
C8—N3—C4—C2	−166.62 (18)	C13—C12—C11—C10	−1.9 (7)
C5—N3—C4—C2	7.0 (2)	C9—C10—C11—C12	−1.1 (7)
C1—C2—C4—N3	−4.1 (2)	C11—C12—C13—C14	3.3 (6)
C3—C2—C4—N3	177.3 (3)	C9—C14—C13—C12	−1.8 (5)

Hydrogen-bond geometry (Å, º) top

Cg1 is the centroid of the C16–C21 phenyl ring.

D—H···A	D—H	H···A	D···A	D—H···A
N4—H4···O1ⁱ	0.86	2.23	2.997 (2)	148
C20—H20···O1ⁱⁱ	0.93	2.49	3.359 (3)	156
C5—H5A···Cg1ⁱⁱ	0.97	2.64	3.508 (3)	150

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

Experimental details

Crystal data
Chemical formula	C₂₁H₁₈N₄O₃
M_r	374.39
Crystal system, space group	Monoclinic, P2₁/c
Temperature (K)	293
a, b, c (Å)	5.32163 (11), 21.1878 (5), 16.4585 (3)
β (°)	96.9378 (17)
V (Å³)	1842.16 (7)
Z	4
Radiation type	Cu Kα
µ (mm⁻¹)	0.76
Crystal size (mm)	0.25 × 0.22 × 0.18

Data collection
Diffractometer	Oxford Diffraction Xcalibur Atlas Gemini ultra diffractometer
Absorption correction	Multi-scan (CrysAlis PRO; Agilent, 2011)
T_min, T_max	0.819, 1.000
No. of measured, independent and observed [I > 2σ(I)] reflections	10256, 3276, 2856
R_int	0.018
(sin θ/λ)_max (Å⁻¹)	0.596

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.053, 0.150, 1.07
No. of reflections	3276
No. of parameters	254
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.62, −0.25

Computer programs: CrysAlis PRO (Agilent, 2011), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), SHELXTL (Sheldrick, 2008).

Hydrogen-bond geometry (Å, º) top

Cg1 is the centroid of the C16–C21 phenyl ring.

D—H···A	D—H	H···A	D···A	D—H···A
N4—H4···O1ⁱ	0.86	2.23	2.997 (2)	148.0
C20—H20···O1ⁱⁱ	0.93	2.49	3.359 (3)	156
C5—H5A···Cg1ⁱⁱ	0.97	2.64	3.508 (3)	150

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

Acknowledgements

This work was supported by the National Natural Science Foundation (81072577).

References

Agilent (2011). CrysAlis PRO. Agilent Technologies, Yarnton, England. Google Scholar
Fancelli, D., et al. (2005). J. Med. Chem. 48, 3080–3084. Web of Science CrossRef PubMed CAS Google Scholar
Gadekar, S. M., Johnson, B. D. & Cohen, E. (1968). J. Med. Chem. 11, 616–618. CrossRef CAS PubMed Web of Science Google Scholar
Guo, X., Bai, X. G., Li, Y. L. & Wang, Y. C. (2010). Acta Cryst. E66, o1108. 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
Xia, W.-B., Bai, X.-G., Liu, H.-T. & Wang, J.-X. (2011). Acta Cryst. E67, o1150. Web of Science CSD CrossRef IUCr Journals Google Scholar

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