Ethyl 2-{4-[(1,5-dibenzyl-2,4-dioxo-2,3,4,5-tetra­hydro-1H-1,5-benzo­diazepin-3-yl)meth­yl]-1H-1,2,3-triazol-1-yl}acetate

Jabli, H.; Kandri Rodi, Y.; Ladeira, S.; Essassi, E.M.; Ng, S.W.

doi:10.1107/S1600536809052696

organic compounds

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ISSN: 2056-9890

Volume 66| Part 1| January 2010| Page o126

doi:10.1107/S1600536809052696

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Ethyl 2-{4-[(1,5-dibenzyl-2,4-dioxo-2,3,4,5-tetrahydro-1H-1,5-benzodiazepin-3-yl)methyl]-1H-1,2,3-triazol-1-yl}acetate

Hind Jabli,^a Y. Kandri Rodi,^a Sonia Ladeira,^b El Mokhtar Essassi ^c and Seik Weng Ng ^d ^*

^aLaboratoire de Chimie Organique Appliquée, Faculté des Sciences et Techniques, Université Sidi Mohamed Ben Abdallah, Fés, Morocco, ^bService de Diffraction X, Laboratoire de Chimie de Coordination, 205 route de Narbonne, 31077 Toulouse Cedex 04, France, ^cLaboratoire de Chimie Organique Hétérocyclique, Pôle de compétences Pharmacochimie, Université Mohammed V-Agdal, BP 1014 Avenue Ibn Batout, Rabat, Morocco, and ^dDepartment of Chemistry, University of Malaya, 50603 Kuala Lumpur, Malaysia
^*Correspondence e-mail: seikweng@um.edu.my

(Received 7 December 2009; accepted 8 December 2009; online 12 December 2009)

The reaction of 1,5-dibenzyl-3-propargyl-1,5-benzodiazepine-2,4-dione with ethyl azidoacetate in the presence of copper sulfate pentahydrate and sodium ascorbate leads to the formation of the title regioisomer, C₃₀H₂₉N₅O₄, which features a phenylene ring fused with a seven-membered diazepinyl ring. The latter ring adopts a boat conformation (with the methyltriazolylacetate-bearing C atom as the prow and the fused-ring C atoms as the stern). The benzyl groups connected to the diazepinyl ring jprotrude from the sides; the methyltriazolylacetate substituent occupies an axial position.

Related literature

For the crystal structure of the parent compound, benzodiazepin-2,4-dione, see: Négrier et al. (2006 ). For the crystal structure of 1,5-dibenzyl-3-propargyl-1,5-benzodiazepine-2,4-dione, see: Jabli et al. (2009 ).

Experimental

Crystal data

C₃₀H₂₉N₅O₄
M_r = 523.58
Monoclinic, P 2₁ /c
a = 14.2015 (5) Å
b = 10.9337 (4) Å
c = 17.9368 (6) Å
β = 95.699 (2)°
V = 2771.37 (17) Å³
Z = 4
Mo Kα radiation
μ = 0.09 mm⁻¹
T = 243 K
0.30 × 0.22 × 0.08 mm

Data collection

Bruker APEXII diffractometer
29097 measured reflections
6377 independent reflections
2690 reflections with I > 2σ(I)
R_int = 0.079
Standard reflections: 0

Refinement

R[F² > 2σ(F²)] = 0.058
wR(F²) = 0.174
S = 1.00
6377 reflections
352 parameters
1 restraint
H-atom parameters constrained
Δρ_max = 0.48 e Å⁻³
Δρ_min = −0.22 e Å⁻³

Data collection: APEX2 (Bruker, 2005 ); cell refinement: SAINT (Bruker, 2005); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: X-SEED (Barbour, 2001 ); software used to prepare material for publication: publCIF (Westrip, 2009 ).

Supporting information

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536809052696/sj2708sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536809052696/sj2708Isup2.hkl

checkCIF report

Related literature top

For the crystal structure of the parent compound, benzodiazepin-2,4-dione, see: Négrier et al. (2006). For the crystal structure of 1,5-dibenzyl-3-propargyl-1,5-benzodiazepine-2,4-dione, see: Jabli et al. (2009).

Experimental top

To a solution 1,5-dibenzyl-1,5-benzodiazepine-2,4-dione (1 mmol) t-butyl alcohol/water (1/2, 8 ml) was added copper sulfate pentahydrate (1 mmol), sodium ascorbate (2 mmol) and ethyl azidoacetate (5 mmol). Stirring was continued for 8 h. The solution was diluted with water (20 ml) and the organic compound extracted with ethyl acetate (2 x 20 ml). The extracts were washed with brine and dried over sodium sulfate. The compound was recrystallized from ether to give colorless crystals.

Computing details top

Data collection: APEX2 (Bruker, 2005); cell refinement: SAINT (Bruker, 2005); data reduction: SAINT (Bruker, 2005); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: X-SEED (Barbour, 2001); software used to prepare material for publication: publCIF (Westrip, 2009).

Figures top

Fig. 1. Thermal ellipsoid plot (Barbour, 2001) of C₃₀H₂₉N₅O₄ at the 70% probability level; hydrogen atoms are drawn as arbitrary radius.

Ethyl 2-{4-[(1,5-dibenzyl-2,4-dioxo-2,3,4,5-tetrahydro-1H-1,5- benzodiazepin-3-yl)methyl]-1H-1,2,3-triazol-1-yl}acetate top

Crystal data top

C₃₀H₂₉N₅O₄	F(000) = 1104
M_r = 523.58	D_x = 1.255 Mg m⁻³
Monoclinic, P2₁/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 2371 reflections
a = 14.2015 (5) Å	θ = 2.2–18.1°
b = 10.9337 (4) Å	µ = 0.09 mm⁻¹
c = 17.9368 (6) Å	T = 243 K
β = 95.699 (2)°	Block, colorless
V = 2771.37 (17) Å³	0.30 × 0.22 × 0.08 mm
Z = 4

Data collection top

Bruker APEXII diffractometer	2690 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	R_int = 0.079
Graphite monochromator	θ_max = 27.5°, θ_min = 1.4°
ϕ and ω scans	h = −15→18
29097 measured reflections	k = −11→14
6377 independent reflections	l = −23→23

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)] = 0.058	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.174	H-atom parameters constrained
S = 1.00	w = 1/[σ²(F_o²) + (0.0719P)² + 0.0345P] where P = (F_o² + 2F_c²)/3
6377 reflections	(Δ/σ)_max = 0.001
352 parameters	Δρ_max = 0.48 e Å⁻³
1 restraint	Δρ_min = −0.22 e Å⁻³

Crystal data top

C₃₀H₂₉N₅O₄	V = 2771.37 (17) Å³
M_r = 523.58	Z = 4
Monoclinic, P2₁/c	Mo Kα radiation
a = 14.2015 (5) Å	µ = 0.09 mm⁻¹
b = 10.9337 (4) Å	T = 243 K
c = 17.9368 (6) Å	0.30 × 0.22 × 0.08 mm
β = 95.699 (2)°

Data collection top

Bruker APEXII diffractometer	2690 reflections with I > 2σ(I)
29097 measured reflections	R_int = 0.079
6377 independent reflections

Refinement top

R[F² > 2σ(F²)] = 0.058	1 restraint
wR(F²) = 0.174	H-atom parameters constrained
S = 1.00	Δρ_max = 0.48 e Å⁻³
6377 reflections	Δρ_min = −0.22 e Å⁻³
352 parameters

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

	x	y	z	U_iso*/U_eq
O1	0.37697 (14)	1.09779 (17)	0.39010 (11)	0.0567 (6)
O2	0.11543 (14)	1.08866 (18)	0.41866 (11)	0.0600 (6)
O3	0.70046 (15)	0.63752 (18)	0.54560 (12)	0.0665 (6)
O4	0.60809 (16)	0.7150 (2)	0.44777 (13)	0.0844 (8)
N1	0.31956 (15)	1.0200 (2)	0.27730 (12)	0.0482 (6)
N2	0.11754 (15)	1.0312 (2)	0.29647 (12)	0.0483 (6)
N3	0.31787 (17)	0.7234 (2)	0.46224 (13)	0.0557 (7)
N4	0.38706 (18)	0.6481 (2)	0.48645 (13)	0.0576 (7)
N5	0.45203 (16)	0.7143 (2)	0.52910 (12)	0.0484 (6)
C1	0.2513 (2)	0.9476 (3)	0.23315 (14)	0.0471 (7)
C2	0.2827 (3)	0.8723 (3)	0.17821 (18)	0.0732 (10)
H2	0.3478	0.8658	0.1735	0.088*
C3	0.2187 (3)	0.8067 (4)	0.1304 (2)	0.0931 (13)
H3	0.2404	0.7552	0.0938	0.112*
C4	0.1223 (3)	0.8172 (3)	0.13675 (19)	0.0830 (11)
H4	0.0786	0.7753	0.1031	0.100*
C5	0.0908 (2)	0.8889 (3)	0.19218 (16)	0.0630 (9)
H5	0.0256	0.8934	0.1971	0.076*
C6	0.1540 (2)	0.9551 (2)	0.24119 (14)	0.0455 (7)
C7	0.38849 (19)	1.0938 (3)	0.23979 (16)	0.0544 (8)
H7A	0.3887	1.1768	0.2604	0.065*
H7B	0.3658	1.0996	0.1865	0.065*
C8	0.49003 (19)	1.0480 (2)	0.24595 (15)	0.0459 (7)
C9	0.5521 (2)	1.1034 (3)	0.20078 (16)	0.0561 (8)
H9	0.5294	1.1643	0.1666	0.067*
C10	0.6470 (2)	1.0702 (3)	0.2054 (2)	0.0703 (10)
H10	0.6875	1.1073	0.1737	0.084*
C11	0.6819 (2)	0.9829 (3)	0.25645 (19)	0.0705 (9)
H11	0.7464	0.9618	0.2604	0.085*
C12	0.6217 (2)	0.9267 (3)	0.30160 (18)	0.0628 (9)
H12	0.6451	0.8667	0.3362	0.075*
C13	0.5257 (2)	0.9588 (3)	0.29596 (16)	0.0558 (8)
H13	0.4849	0.9194	0.3265	0.067*
C14	0.0279 (2)	1.0971 (3)	0.27638 (17)	0.0630 (9)
H14A	0.0149	1.1499	0.3183	0.076*
H14B	−0.0237	1.0375	0.2688	0.076*
C15	0.0286 (2)	1.1742 (3)	0.20694 (15)	0.0498 (7)
C16	−0.0512 (2)	1.1786 (3)	0.15552 (17)	0.0598 (8)
H16	−0.1045	1.1314	0.1636	0.072*
C17	−0.0530 (3)	1.2522 (3)	0.09205 (19)	0.0702 (10)
H17	−0.1071	1.2538	0.0574	0.084*
C18	0.0242 (3)	1.3224 (3)	0.08008 (19)	0.0728 (10)
H18	0.0227	1.3720	0.0372	0.087*
C19	0.1046 (2)	1.3204 (3)	0.1311 (2)	0.0711 (9)
H19	0.1572	1.3689	0.1231	0.085*
C20	0.1064 (2)	1.2457 (3)	0.19446 (18)	0.0637 (9)
H20	0.1607	1.2438	0.2289	0.076*
C21	0.32027 (19)	1.0305 (2)	0.35331 (16)	0.0449 (7)
C22	0.24439 (18)	0.9589 (2)	0.38906 (14)	0.0408 (6)
H22	0.2373	0.8774	0.3652	0.049*
C23	0.15274 (19)	1.0309 (2)	0.37117 (16)	0.0456 (7)
C24	0.27037 (19)	0.9424 (2)	0.47331 (14)	0.0475 (7)
H24A	0.2986	1.0181	0.4945	0.057*
H24B	0.2129	0.9260	0.4977	0.057*
C25	0.33895 (19)	0.8388 (2)	0.48895 (14)	0.0424 (7)
C26	0.4240 (2)	0.8323 (2)	0.53126 (15)	0.0493 (7)
H26	0.4567	0.8969	0.5568	0.059*
C27	0.5400 (2)	0.6571 (3)	0.56053 (16)	0.0526 (8)
H27A	0.5294	0.5695	0.5674	0.063*
H27B	0.5594	0.6927	0.6098	0.063*
C28	0.6185 (2)	0.6746 (3)	0.51023 (19)	0.0557 (8)
C29	0.7809 (2)	0.6436 (4)	0.5009 (2)	0.0954 (13)
H29A	0.7979	0.7291	0.4928	0.114*
H29B	0.7645	0.6052	0.4520	0.114*
C30	0.8613 (3)	0.5788 (4)	0.5417 (3)	0.155 (2)
H30A	0.9154	0.5819	0.5127	0.232*
H30B	0.8441	0.4942	0.5493	0.232*
H30C	0.8774	0.6177	0.5899	0.232*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
O1	0.0539 (13)	0.0544 (12)	0.0612 (13)	−0.0108 (10)	0.0030 (11)	−0.0064 (10)
O2	0.0620 (14)	0.0655 (13)	0.0542 (13)	0.0135 (11)	0.0145 (11)	−0.0095 (11)
O3	0.0555 (14)	0.0591 (14)	0.0836 (16)	0.0036 (11)	−0.0003 (13)	0.0102 (11)
O4	0.0740 (17)	0.120 (2)	0.0600 (15)	0.0123 (14)	0.0093 (13)	0.0211 (14)
N1	0.0452 (14)	0.0583 (15)	0.0424 (14)	−0.0054 (12)	0.0108 (12)	0.0026 (11)
N2	0.0456 (14)	0.0554 (14)	0.0442 (14)	0.0092 (11)	0.0058 (11)	0.0036 (11)
N3	0.0560 (16)	0.0506 (15)	0.0588 (16)	0.0016 (13)	−0.0017 (13)	−0.0098 (12)
N4	0.0586 (17)	0.0468 (14)	0.0656 (17)	−0.0035 (13)	−0.0027 (14)	−0.0102 (13)
N5	0.0538 (15)	0.0400 (13)	0.0500 (14)	−0.0046 (12)	−0.0013 (12)	0.0011 (11)
C1	0.0504 (19)	0.0582 (18)	0.0341 (15)	−0.0024 (15)	0.0103 (14)	−0.0017 (13)
C2	0.074 (2)	0.092 (3)	0.059 (2)	−0.005 (2)	0.0277 (19)	−0.0179 (19)
C3	0.106 (3)	0.117 (3)	0.060 (2)	−0.021 (3)	0.029 (2)	−0.041 (2)
C4	0.096 (3)	0.107 (3)	0.047 (2)	−0.036 (2)	0.010 (2)	−0.022 (2)
C5	0.063 (2)	0.080 (2)	0.0463 (19)	−0.0135 (18)	0.0049 (17)	0.0028 (17)
C6	0.0501 (19)	0.0516 (17)	0.0346 (15)	−0.0020 (14)	0.0037 (14)	0.0011 (13)
C7	0.0527 (19)	0.0597 (19)	0.0523 (18)	−0.0017 (15)	0.0127 (15)	0.0151 (14)
C8	0.0487 (18)	0.0422 (16)	0.0476 (17)	−0.0058 (14)	0.0077 (14)	−0.0022 (14)
C9	0.055 (2)	0.0580 (19)	0.0560 (19)	−0.0057 (16)	0.0088 (16)	0.0116 (15)
C10	0.053 (2)	0.078 (2)	0.082 (2)	−0.0051 (18)	0.0116 (19)	0.0160 (19)
C11	0.055 (2)	0.077 (2)	0.081 (2)	0.0072 (18)	0.012 (2)	0.007 (2)
C12	0.068 (2)	0.0550 (19)	0.066 (2)	0.0146 (17)	0.0066 (18)	0.0096 (16)
C13	0.064 (2)	0.0494 (18)	0.0564 (19)	0.0017 (16)	0.0162 (16)	0.0082 (15)
C14	0.0445 (19)	0.079 (2)	0.066 (2)	0.0117 (16)	0.0066 (16)	0.0145 (17)
C15	0.0445 (18)	0.0548 (18)	0.0497 (18)	0.0076 (15)	0.0027 (15)	0.0049 (14)
C16	0.051 (2)	0.065 (2)	0.064 (2)	0.0076 (16)	0.0083 (17)	0.0019 (17)
C17	0.067 (2)	0.081 (3)	0.061 (2)	0.020 (2)	0.0015 (19)	0.0083 (18)
C18	0.095 (3)	0.067 (2)	0.058 (2)	0.022 (2)	0.016 (2)	0.0151 (17)
C19	0.071 (2)	0.067 (2)	0.078 (2)	−0.0035 (18)	0.019 (2)	0.0073 (19)
C20	0.055 (2)	0.069 (2)	0.067 (2)	−0.0023 (17)	0.0032 (17)	0.0048 (17)
C21	0.0426 (17)	0.0426 (16)	0.0500 (18)	0.0038 (14)	0.0067 (15)	−0.0001 (14)
C22	0.0447 (16)	0.0393 (15)	0.0391 (15)	0.0020 (13)	0.0082 (13)	−0.0030 (12)
C23	0.0482 (18)	0.0458 (16)	0.0438 (17)	−0.0001 (14)	0.0102 (15)	−0.0004 (13)
C24	0.0536 (18)	0.0520 (17)	0.0372 (15)	0.0009 (14)	0.0068 (14)	−0.0028 (13)
C25	0.0478 (18)	0.0437 (16)	0.0359 (15)	−0.0039 (14)	0.0048 (14)	−0.0012 (12)
C26	0.059 (2)	0.0362 (16)	0.0519 (18)	−0.0065 (14)	0.0006 (16)	−0.0020 (13)
C27	0.059 (2)	0.0411 (16)	0.0550 (18)	0.0026 (14)	−0.0058 (16)	0.0086 (14)
C28	0.056 (2)	0.0488 (18)	0.061 (2)	0.0044 (15)	−0.0026 (18)	0.0041 (15)
C29	0.060 (2)	0.110 (3)	0.118 (3)	0.012 (2)	0.017 (3)	0.013 (3)
C30	0.089 (3)	0.141 (5)	0.235 (7)	0.038 (3)	0.021 (4)	0.056 (4)

Geometric parameters (Å, º) top

O1—C21	1.233 (3)	C11—H11	0.9400
O2—C23	1.223 (3)	C12—C13	1.402 (4)
O3—C28	1.333 (3)	C12—H12	0.9400
O3—C29	1.461 (4)	C13—H13	0.9400
O4—C28	1.200 (3)	C14—C15	1.504 (4)
N1—C21	1.367 (3)	C14—H14A	0.9800
N1—C1	1.429 (3)	C14—H14B	0.9800
N1—C7	1.481 (3)	C15—C16	1.388 (4)
N2—C23	1.383 (3)	C15—C20	1.390 (4)
N2—C6	1.430 (3)	C16—C17	1.392 (4)
N2—C14	1.477 (3)	C16—H16	0.9400
N3—N4	1.322 (3)	C17—C18	1.372 (5)
N3—C25	1.371 (3)	C17—H17	0.9400
N4—N5	1.350 (3)	C18—C19	1.391 (5)
N5—C26	1.351 (3)	C18—H18	0.9400
N5—C27	1.460 (3)	C19—C20	1.397 (4)
C1—C2	1.391 (4)	C19—H19	0.9400
C1—C6	1.405 (4)	C20—H20	0.9400
C2—C3	1.385 (5)	C21—C22	1.524 (4)
C2—H2	0.9400	C22—C23	1.528 (4)
C3—C4	1.389 (5)	C22—C24	1.530 (3)
C3—H3	0.9400	C22—H22	0.9900
C4—C5	1.376 (4)	C24—C25	1.502 (4)
C4—H4	0.9400	C24—H24A	0.9800
C5—C6	1.395 (4)	C24—H24B	0.9800
C5—H5	0.9400	C25—C26	1.363 (4)
C7—C8	1.520 (4)	C26—H26	0.9400
C7—H7A	0.9800	C27—C28	1.513 (4)
C7—H7B	0.9800	C27—H27A	0.9800
C8—C13	1.386 (4)	C27—H27B	0.9800
C8—C9	1.394 (4)	C29—C30	1.475 (4)
C9—C10	1.390 (4)	C29—H29A	0.9800
C9—H9	0.9400	C29—H29B	0.9800
C10—C11	1.381 (4)	C30—H30A	0.9700
C10—H10	0.9400	C30—H30B	0.9700
C11—C12	1.379 (4)	C30—H30C	0.9700

C28—O3—C29	114.8 (3)	C20—C15—C14	121.3 (3)
C21—N1—C1	122.5 (2)	C15—C16—C17	120.7 (3)
C21—N1—C7	117.9 (2)	C15—C16—H16	119.6
C1—N1—C7	119.5 (2)	C17—C16—H16	119.6
C23—N2—C6	123.3 (2)	C18—C17—C16	120.1 (3)
C23—N2—C14	117.2 (2)	C18—C17—H17	120.0
C6—N2—C14	118.5 (2)	C16—C17—H17	120.0
N4—N3—C25	109.2 (2)	C17—C18—C19	120.3 (3)
N3—N4—N5	107.2 (2)	C17—C18—H18	119.9
N4—N5—C26	110.0 (2)	C19—C18—H18	119.9
N4—N5—C27	120.0 (2)	C18—C19—C20	119.5 (3)
C26—N5—C27	129.9 (2)	C18—C19—H19	120.3
C2—C1—C6	119.6 (3)	C20—C19—H19	120.3
C2—C1—N1	118.2 (3)	C15—C20—C19	120.6 (3)
C6—C1—N1	122.1 (2)	C15—C20—H20	119.7
C3—C2—C1	120.5 (3)	C19—C20—H20	119.7
C3—C2—H2	119.7	O1—C21—N1	121.6 (3)
C1—C2—H2	119.7	O1—C21—C22	122.2 (2)
C2—C3—C4	119.8 (3)	N1—C21—C22	116.2 (2)
C2—C3—H3	120.1	C21—C22—C23	105.7 (2)
C4—C3—H3	120.1	C21—C22—C24	111.4 (2)
C5—C4—C3	120.0 (3)	C23—C22—C24	112.6 (2)
C5—C4—H4	120.0	C21—C22—H22	109.0
C3—C4—H4	120.0	C23—C22—H22	109.0
C4—C5—C6	121.1 (3)	C24—C22—H22	109.0
C4—C5—H5	119.5	O2—C23—N2	122.3 (3)
C6—C5—H5	119.5	O2—C23—C22	122.6 (2)
C5—C6—C1	118.9 (3)	N2—C23—C22	115.0 (2)
C5—C6—N2	118.9 (3)	C25—C24—C22	111.2 (2)
C1—C6—N2	122.2 (2)	C25—C24—H24A	109.4
N1—C7—C8	116.9 (2)	C22—C24—H24A	109.4
N1—C7—H7A	108.1	C25—C24—H24B	109.4
C8—C7—H7A	108.1	C22—C24—H24B	109.4
N1—C7—H7B	108.1	H24A—C24—H24B	108.0
C8—C7—H7B	108.1	C26—C25—N3	107.3 (2)
H7A—C7—H7B	107.3	C26—C25—C24	131.7 (2)
C13—C8—C9	118.1 (3)	N3—C25—C24	120.9 (2)
C13—C8—C7	124.2 (3)	N5—C26—C25	106.3 (2)
C9—C8—C7	117.7 (2)	N5—C26—H26	126.8
C10—C9—C8	121.2 (3)	C25—C26—H26	126.8
C10—C9—H9	119.4	N5—C27—C28	111.6 (2)
C8—C9—H9	119.4	N5—C27—H27A	109.3
C11—C10—C9	120.1 (3)	C28—C27—H27A	109.3
C11—C10—H10	119.9	N5—C27—H27B	109.3
C9—C10—H10	119.9	C28—C27—H27B	109.3
C10—C11—C12	119.7 (3)	H27A—C27—H27B	108.0
C10—C11—H11	120.2	O4—C28—O3	125.2 (3)
C12—C11—H11	120.2	O4—C28—C27	125.0 (3)
C11—C12—C13	120.1 (3)	O3—C28—C27	109.7 (3)
C11—C12—H12	120.0	O3—C29—C30	108.4 (3)
C13—C12—H12	120.0	O3—C29—H29A	110.0
C8—C13—C12	120.9 (3)	C30—C29—H29A	110.0
C8—C13—H13	119.6	O3—C29—H29B	110.0
C12—C13—H13	119.6	C30—C29—H29B	110.0
N2—C14—C15	113.5 (2)	H29A—C29—H29B	108.4
N2—C14—H14A	108.9	C29—C30—H30A	109.5
C15—C14—H14A	108.9	C29—C30—H30B	109.5
N2—C14—H14B	108.9	H30A—C30—H30B	109.5
C15—C14—H14B	108.9	C29—C30—H30C	109.5
H14A—C14—H14B	107.7	H30A—C30—H30C	109.5
C16—C15—C20	118.8 (3)	H30B—C30—H30C	109.5
C16—C15—C14	119.9 (3)

C25—N3—N4—N5	0.5 (3)	C15—C16—C17—C18	−0.6 (5)
N3—N4—N5—C26	−0.5 (3)	C16—C17—C18—C19	0.0 (5)
N3—N4—N5—C27	−176.5 (2)	C17—C18—C19—C20	0.4 (5)
C21—N1—C1—C2	−135.6 (3)	C16—C15—C20—C19	−0.3 (4)
C7—N1—C1—C2	48.8 (4)	C14—C15—C20—C19	−177.5 (3)
C21—N1—C1—C6	47.6 (4)	C18—C19—C20—C15	−0.3 (5)
C7—N1—C1—C6	−128.0 (3)	C1—N1—C21—O1	−176.6 (2)
C6—C1—C2—C3	1.4 (5)	C7—N1—C21—O1	−0.9 (4)
N1—C1—C2—C3	−175.5 (3)	C1—N1—C21—C22	0.8 (4)
C1—C2—C3—C4	0.8 (6)	C7—N1—C21—C22	176.5 (2)
C2—C3—C4—C5	−2.5 (6)	O1—C21—C22—C23	101.2 (3)
C3—C4—C5—C6	2.1 (5)	N1—C21—C22—C23	−76.1 (3)
C4—C5—C6—C1	0.0 (4)	O1—C21—C22—C24	−21.4 (3)
C4—C5—C6—N2	178.2 (3)	N1—C21—C22—C24	161.2 (2)
C2—C1—C6—C5	−1.8 (4)	C6—N2—C23—O2	−173.5 (2)
N1—C1—C6—C5	175.0 (2)	C14—N2—C23—O2	−4.5 (4)
C2—C1—C6—N2	−179.8 (3)	C6—N2—C23—C22	9.6 (4)
N1—C1—C6—N2	−3.1 (4)	C14—N2—C23—C22	178.7 (2)
C23—N2—C6—C5	132.3 (3)	C21—C22—C23—O2	−108.4 (3)
C14—N2—C6—C5	−36.6 (4)	C24—C22—C23—O2	13.5 (4)
C23—N2—C6—C1	−49.6 (4)	C21—C22—C23—N2	68.5 (3)
C14—N2—C6—C1	141.4 (3)	C24—C22—C23—N2	−169.7 (2)
C21—N1—C7—C8	77.6 (3)	C21—C22—C24—C25	−80.8 (3)
C1—N1—C7—C8	−106.6 (3)	C23—C22—C24—C25	160.6 (2)
N1—C7—C8—C13	−13.9 (4)	N4—N3—C25—C26	−0.3 (3)
N1—C7—C8—C9	169.2 (2)	N4—N3—C25—C24	−177.0 (2)
C13—C8—C9—C10	0.2 (4)	C22—C24—C25—C26	128.0 (3)
C7—C8—C9—C10	177.3 (3)	C22—C24—C25—N3	−56.2 (3)
C8—C9—C10—C11	−1.4 (5)	N4—N5—C26—C25	0.3 (3)
C9—C10—C11—C12	1.5 (5)	C27—N5—C26—C25	175.8 (3)
C10—C11—C12—C13	−0.4 (5)	N3—C25—C26—N5	0.0 (3)
C9—C8—C13—C12	0.9 (4)	C24—C25—C26—N5	176.2 (3)
C7—C8—C13—C12	−176.0 (3)	N4—N5—C27—C28	93.4 (3)
C11—C12—C13—C8	−0.8 (5)	C26—N5—C27—C28	−81.7 (3)
C23—N2—C14—C15	136.3 (3)	C29—O3—C28—O4	−2.8 (5)
C6—N2—C14—C15	−54.1 (4)	C29—O3—C28—C27	176.7 (3)
N2—C14—C15—C16	139.8 (3)	N5—C27—C28—O4	−9.6 (4)
N2—C14—C15—C20	−43.0 (4)	N5—C27—C28—O3	170.8 (2)
C20—C15—C16—C17	0.7 (4)	C28—O3—C29—C30	−169.4 (3)
C14—C15—C16—C17	178.0 (3)

Experimental details

Crystal data
Chemical formula	C₃₀H₂₉N₅O₄
M_r	523.58
Crystal system, space group	Monoclinic, P2₁/c
Temperature (K)	243
a, b, c (Å)	14.2015 (5), 10.9337 (4), 17.9368 (6)
β (°)	95.699 (2)
V (Å³)	2771.37 (17)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.09
Crystal size (mm)	0.30 × 0.22 × 0.08

Data collection
Diffractometer	Bruker APEXII diffractometer
Absorption correction	–
No. of measured, independent and observed [I > 2σ(I)] reflections	29097, 6377, 2690
R_int	0.079
(sin θ/λ)_max (Å⁻¹)	0.650

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.058, 0.174, 1.00
No. of reflections	6377
No. of parameters	352
No. of restraints	1
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.48, −0.22

Computer programs: APEX2 (Bruker, 2005), SAINT (Bruker, 2005), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), X-SEED (Barbour, 2001), publCIF (Westrip, 2009).

Acknowledgements

We thank Université Mohammed V-Agdal, University Sidi Mohammed Ben Abdallah and the University of Malaya for supporting this study.

References

Barbour, L. J. (2001). J. Supramol. Chem. 1, 189–191. CrossRef CAS Google Scholar
Bruker (2005). APEX2 and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
Jabli, H., Ouazzani Chahdi, F., Garrigues, B., Essassi, E. M. & Ng, S. W. (2009). Acta Cryst. E65, o3149. Web of Science CSD CrossRef IUCr Journals Google Scholar
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