4-[(1,5-Dibenzyl-2,4-dioxo-2,3,4,5-tetra­hydro-1H-1,5-benzodiazepin-3-yl)meth­yl]-1-n-octyl-1H-1,2,3-triazole

Jabli, H.; Ouazzani Chahdi, F.; Saffon, N.; Essassi, E.M.; Ng, S.W.

doi:10.1107/S1600536809054476

organic compounds

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ISSN: 2056-9890

Volume 66| Part 1| January 2010| Page o231

doi:10.1107/S1600536809054476

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4-[(1,5-Dibenzyl-2,4-dioxo-2,3,4,5-tetrahydro-1H-1,5-benzodiazepin-3-yl)methyl]-1-n-octyl-1H-1,2,3-triazole

Hind Jabli,^a F. Ouazzani Chahdi,^a Natalie Saffon,^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 Commun Rayons-X FR2599, Université Paul Sabatier, Bâtiment 2R1, 118 Route de Narbonne, Toulouse, 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 15 December 2009; accepted 17 December 2009; online 24 December 2009)

The reaction of 1,5-dibenzyl-3-propargyl-1,5-benzodiazepine-2,4-dione with 1-azido-n-octane in the presence of catalysts leads to the formation of the title compound, C₃₄H₃₉N₅O₂, which features a phenylene ring fused with a seven-membered diazepinyl ring. The latter ring adopts a boat conformation with the octyltriazolylmethyl-bearing C atom as the prow and the fused-ring C atoms as the stern. The octyltriazolylmethyl substituent occupies an axial position.

Related literature

For the crystal structures of other N-substituted homologues, see: Jabli et al. (2009 , 2010 ).

Experimental

Crystal data

C₃₄H₃₉N₅O₂
M_r = 549.70
Orthorhombic, P 2₁ 2₁ 2₁
a = 9.1797 (2) Å
b = 10.4238 (2) Å
c = 31.4716 (7) Å
V = 3011.4 (1) Å³
Z = 4
Mo Kα radiation
μ = 0.08 mm⁻¹
T = 193 K
0.30 × 0.16 × 0.10 mm

Data collection

Bruker APEXII diffractometer
44767 measured reflections
3027 independent reflections
2307 reflections with I > 2σ(I)
R_int = 0.072

Refinement

R[F² > 2σ(F²)] = 0.057
wR(F²) = 0.174
S = 1.02
3027 reflections
370 parameters
59 restraints
H-atom parameters constrained
Δρ_max = 0.59 e Å⁻³
Δρ_min = −0.41 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, 2010 ).

Supporting information

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536809054476/bt5142sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536809054476/bt5142Isup2.hkl

checkCIF report

Related literature top

For the crystal structures of other N-substituted homologues, see: Jabli et al. (2009, 2010).

Experimental top

To a solution 1,5-dibenzyl-3-propargyl-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 1-azido-n-octane (5 mmol). Stirring was continued for 12 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 ethyl acetate/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, 2010).

Figures top

Fig. 1. Anisotropic displacement ellipsoid plot (Barbour, 2001) of C₃₄H₂₃N₅O₂ at the 70% probability level; hydrogen atoms are drawn as arbitrary radius.

4-[(1,5-Dibenzyl-2,4-dioxo-2,3,4,5-tetrahydro-1H-1,5-benzodiazepin- 3-yl)methyl]-1-n-octyl-1H-1,2,3-triazole top

Crystal data top

C₃₄H₃₉N₅O₂	F(000) = 1176
M_r = 549.70	D_x = 1.212 Mg m⁻³
Orthorhombic, P2₁2₁2₁	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2ac 2ab	Cell parameters from 5123 reflections
a = 9.1797 (2) Å	θ = 2.3–19.1°
b = 10.4238 (2) Å	µ = 0.08 mm⁻¹
c = 31.4716 (7) Å	T = 193 K
V = 3011.4 (1) Å³	Block, colorless
Z = 4	0.30 × 0.16 × 0.10 mm

Data collection top

Bruker APEXII diffractometer	2307 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	R_int = 0.072
Graphite monochromator	θ_max = 25.0°, θ_min = 1.3°
ϕ and ω scans	h = −10→10
44767 measured reflections	k = −11→12
3027 independent reflections	l = −37→37

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)] = 0.057	H-atom parameters constrained
wR(F²) = 0.174	w = 1/[σ²(F_o²) + (0.1036P)² + 1.5833P] where P = (F_o² + 2F_c²)/3
S = 1.02	(Δ/σ)_max = 0.001
3027 reflections	Δρ_max = 0.59 e Å⁻³
370 parameters	Δρ_min = −0.41 e Å⁻³
59 restraints	Absolute structure: Friedel pairs were merged
Primary atom site location: structure-invariant direct methods

Crystal data top

C₃₄H₃₉N₅O₂	V = 3011.4 (1) Å³
M_r = 549.70	Z = 4
Orthorhombic, P2₁2₁2₁	Mo Kα radiation
a = 9.1797 (2) Å	µ = 0.08 mm⁻¹
b = 10.4238 (2) Å	T = 193 K
c = 31.4716 (7) Å	0.30 × 0.16 × 0.10 mm

Data collection top

Bruker APEXII diffractometer	2307 reflections with I > 2σ(I)
44767 measured reflections	R_int = 0.072
3027 independent reflections

Refinement top

R[F² > 2σ(F²)] = 0.057	59 restraints
wR(F²) = 0.174	H-atom parameters constrained
S = 1.02	Δρ_max = 0.59 e Å⁻³
3027 reflections	Δρ_min = −0.41 e Å⁻³
370 parameters	Absolute structure: Friedel pairs were merged

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

	x	y	z	U_iso*/U_eq
O1	0.6191 (3)	0.4931 (3)	0.14072 (10)	0.0418 (8)
O2	0.6411 (3)	0.6919 (4)	0.04134 (9)	0.0449 (8)
N1	0.8576 (4)	0.4659 (3)	0.12497 (11)	0.0316 (8)
N2	0.8703 (4)	0.6098 (3)	0.04556 (11)	0.0312 (8)
N3	0.7316 (5)	0.8647 (5)	0.18835 (15)	0.0663 (14)
N4	0.7049 (5)	0.8835 (5)	0.22909 (16)	0.0658 (15)
N5	0.5823 (5)	0.8206 (4)	0.23825 (13)	0.0453 (10)
C1	0.9921 (5)	0.5125 (4)	0.10829 (13)	0.0306 (10)
C2	1.1212 (5)	0.4862 (5)	0.12995 (15)	0.0383 (11)
H2	1.1178	0.4408	0.1561	0.046*
C3	1.2544 (5)	0.5254 (5)	0.11379 (16)	0.0434 (12)
H3	1.3415	0.5062	0.1288	0.052*
C4	1.2608 (5)	0.5919 (5)	0.07613 (16)	0.0432 (12)
H4	1.3524	0.6176	0.0650	0.052*
C5	1.1341 (5)	0.6214 (4)	0.05445 (14)	0.0356 (10)
H5	1.1393	0.6689	0.0287	0.043*
C6	0.9983 (5)	0.5823 (4)	0.06998 (13)	0.0295 (10)
C7	0.7468 (5)	0.6614 (4)	0.06302 (13)	0.0323 (10)
C8	0.7454 (5)	0.6736 (4)	0.11111 (13)	0.0327 (10)
H8	0.8395	0.7117	0.1209	0.039*
C9	0.7325 (5)	0.5370 (4)	0.12750 (13)	0.0312 (10)
C10	0.8521 (5)	0.3333 (4)	0.14053 (13)	0.0355 (10)
H10A	0.9323	0.2846	0.1270	0.043*
H10B	0.7593	0.2944	0.1310	0.043*
C11	0.8638 (5)	0.3163 (4)	0.18838 (13)	0.0325 (9)
C12	0.8477 (5)	0.1925 (5)	0.20461 (14)	0.0386 (11)
H12	0.8293	0.1228	0.1859	0.046*
C13	0.8583 (6)	0.1711 (5)	0.24805 (16)	0.0488 (13)
H13	0.8454	0.0869	0.2590	0.059*
C14	0.8876 (6)	0.2714 (6)	0.27544 (17)	0.0535 (14)
H14	0.8957	0.2567	0.3051	0.064*
C15	0.9048 (6)	0.3930 (6)	0.25920 (16)	0.0522 (14)
H15	0.9262	0.4622	0.2779	0.063*
C16	0.8913 (5)	0.4160 (5)	0.21615 (14)	0.0411 (11)
H16	0.9010	0.5010	0.2056	0.049*
C17	0.8803 (5)	0.6010 (4)	−0.00113 (12)	0.0335 (10)
H17A	0.9558	0.6615	−0.0112	0.040*
H17B	0.7861	0.6278	−0.0136	0.040*
C18	0.9170 (5)	0.4679 (5)	−0.01692 (14)	0.0358 (10)
C19	0.8245 (6)	0.3651 (5)	−0.00935 (19)	0.0567 (15)
H19	0.7407	0.3772	0.0079	0.068*
C20	0.8518 (8)	0.2465 (6)	−0.0263 (2)	0.078 (2)
H20	0.7872	0.1770	−0.0211	0.093*
C21	0.9754 (8)	0.2290 (6)	−0.0514 (2)	0.0731 (19)
H21	0.9946	0.1477	−0.0638	0.088*
C22	1.0674 (7)	0.3274 (7)	−0.05782 (19)	0.0701 (18)
H22	1.1529	0.3146	−0.0743	0.084*
C23	1.0392 (6)	0.4459 (6)	−0.04097 (15)	0.0476 (13)
H23	1.1055	0.5142	−0.0460	0.057*
C24	0.6185 (5)	0.7586 (5)	0.12581 (14)	0.0420 (11)
H24A	0.6194	0.8394	0.1092	0.050*
H24B	0.5255	0.7141	0.1198	0.050*
C25	0.6250 (5)	0.7901 (4)	0.17170 (14)	0.0381 (11)
C26	0.5306 (5)	0.7603 (5)	0.20384 (15)	0.0438 (12)
H26	0.4462	0.7079	0.2021	0.053*
C27	0.5207 (7)	0.8285 (6)	0.28125 (16)	0.0652 (16)
H27A	0.4189	0.7973	0.2803	0.078*
H27B	0.5181	0.9198	0.2900	0.078*
C28	0.6026 (10)	0.7531 (7)	0.3147 (2)	0.104 (3)
H28A	0.7003	0.7919	0.3182	0.125*
H28B	0.5507	0.7625	0.3421	0.125*
C29	0.6209 (9)	0.6171 (6)	0.3060 (2)	0.099 (2)
H29A	0.6933	0.6065	0.2830	0.119*
H29B	0.5271	0.5817	0.2958	0.119*
C30	0.6720 (7)	0.5384 (6)	0.3458 (2)	0.0790 (19)
H30A	0.5954	0.5441	0.3679	0.095*
H30B	0.6807	0.4471	0.3375	0.095*
C31	0.8145 (6)	0.5805 (6)	0.36514 (19)	0.0740 (19)
H31A	0.7996	0.6630	0.3801	0.089*
H31B	0.8861	0.5951	0.3421	0.089*
C32	0.8765 (7)	0.4832 (7)	0.39625 (19)	0.0773 (19)
H32A	0.9042	0.4045	0.3806	0.093*
H32B	0.8004	0.4597	0.4172	0.093*
C33	1.0108 (7)	0.5354 (8)	0.4200 (2)	0.088 (2)
H33A	1.0927	0.5444	0.3998	0.105*
H33B	0.9881	0.6216	0.4314	0.105*
C34	1.0553 (8)	0.4517 (8)	0.4550 (2)	0.086 (2)
H34A	1.1417	0.4876	0.4689	0.129*
H34B	1.0782	0.3662	0.4438	0.129*
H34C	0.9758	0.4450	0.4756	0.129*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
O1	0.0256 (16)	0.055 (2)	0.0451 (18)	−0.0050 (16)	0.0030 (14)	0.0068 (15)
O2	0.0338 (17)	0.066 (2)	0.0345 (16)	0.0123 (18)	−0.0067 (15)	0.0071 (16)
N1	0.0299 (19)	0.0324 (19)	0.0325 (18)	0.0024 (17)	0.0018 (16)	0.0069 (16)
N2	0.0281 (18)	0.038 (2)	0.0270 (18)	0.0016 (18)	−0.0004 (16)	0.0033 (15)
N3	0.061 (3)	0.084 (4)	0.054 (3)	−0.025 (3)	0.014 (2)	−0.012 (3)
N4	0.058 (3)	0.078 (4)	0.062 (3)	−0.026 (3)	0.011 (2)	−0.026 (3)
N5	0.039 (2)	0.054 (3)	0.043 (2)	0.005 (2)	0.0033 (18)	−0.009 (2)
C1	0.027 (2)	0.034 (2)	0.031 (2)	0.003 (2)	0.0016 (18)	0.0002 (19)
C2	0.032 (2)	0.044 (3)	0.039 (2)	0.007 (2)	−0.003 (2)	0.005 (2)
C3	0.029 (2)	0.050 (3)	0.051 (3)	0.007 (2)	−0.003 (2)	0.002 (3)
C4	0.028 (2)	0.050 (3)	0.052 (3)	0.000 (2)	0.007 (2)	0.000 (3)
C5	0.028 (2)	0.039 (2)	0.039 (2)	−0.002 (2)	0.002 (2)	0.002 (2)
C6	0.026 (2)	0.032 (2)	0.030 (2)	0.004 (2)	0.0005 (18)	−0.0012 (18)
C7	0.028 (2)	0.038 (2)	0.031 (2)	0.003 (2)	0.0000 (18)	0.004 (2)
C8	0.025 (2)	0.038 (2)	0.035 (2)	0.005 (2)	0.0011 (18)	0.000 (2)
C9	0.031 (2)	0.039 (2)	0.024 (2)	0.003 (2)	0.0012 (18)	0.0041 (19)
C10	0.040 (2)	0.031 (2)	0.035 (2)	−0.001 (2)	−0.004 (2)	0.0020 (19)
C11	0.025 (2)	0.035 (2)	0.037 (2)	0.001 (2)	0.0014 (19)	0.0009 (19)
C12	0.041 (3)	0.034 (2)	0.041 (3)	0.000 (2)	0.002 (2)	0.004 (2)
C13	0.044 (3)	0.049 (3)	0.053 (3)	0.003 (3)	−0.004 (2)	0.020 (3)
C14	0.049 (3)	0.072 (4)	0.040 (3)	−0.003 (3)	−0.003 (2)	0.012 (3)
C15	0.059 (3)	0.059 (3)	0.039 (3)	−0.011 (3)	−0.004 (2)	−0.003 (2)
C16	0.044 (3)	0.040 (3)	0.039 (3)	−0.007 (2)	0.004 (2)	0.002 (2)
C17	0.033 (2)	0.040 (2)	0.028 (2)	0.002 (2)	0.0015 (19)	0.0038 (18)
C18	0.033 (2)	0.042 (3)	0.032 (2)	−0.001 (2)	−0.0010 (19)	0.002 (2)
C19	0.053 (3)	0.041 (3)	0.076 (4)	−0.004 (3)	0.009 (3)	0.000 (3)
C20	0.074 (4)	0.047 (3)	0.112 (6)	−0.005 (4)	−0.011 (4)	−0.005 (4)
C21	0.078 (5)	0.054 (4)	0.088 (5)	0.020 (4)	−0.020 (4)	−0.027 (3)
C22	0.062 (4)	0.084 (5)	0.064 (4)	0.019 (4)	0.008 (3)	−0.023 (4)
C23	0.042 (3)	0.057 (3)	0.043 (3)	0.006 (3)	0.007 (2)	−0.008 (3)
C24	0.032 (2)	0.050 (3)	0.044 (3)	0.013 (2)	−0.001 (2)	−0.003 (2)
C25	0.027 (2)	0.040 (3)	0.047 (3)	0.006 (2)	0.004 (2)	−0.005 (2)
C26	0.036 (3)	0.052 (3)	0.043 (3)	−0.005 (2)	0.004 (2)	−0.005 (2)
C27	0.065 (3)	0.087 (4)	0.044 (3)	0.000 (4)	0.004 (3)	−0.012 (3)
C28	0.113 (6)	0.116 (6)	0.083 (5)	0.011 (5)	0.017 (5)	0.006 (5)
C29	0.082 (5)	0.112 (6)	0.103 (5)	0.006 (5)	−0.004 (4)	−0.023 (5)
C30	0.071 (4)	0.072 (4)	0.094 (5)	−0.003 (4)	−0.002 (4)	0.007 (4)
C31	0.076 (4)	0.063 (4)	0.083 (4)	−0.018 (3)	0.020 (3)	−0.016 (3)
C32	0.070 (4)	0.090 (4)	0.072 (4)	−0.017 (4)	0.014 (3)	−0.001 (3)
C33	0.078 (4)	0.091 (5)	0.093 (5)	−0.015 (4)	0.008 (4)	0.013 (4)
C34	0.068 (4)	0.091 (5)	0.099 (5)	−0.006 (4)	0.001 (4)	0.019 (4)

Geometric parameters (Å, º) top

O1—C9	1.211 (5)	C17—H17A	0.9900
O2—C7	1.228 (5)	C17—H17B	0.9900
N1—C9	1.369 (6)	C18—C23	1.373 (6)
N1—C1	1.426 (5)	C18—C19	1.388 (7)
N1—C10	1.468 (6)	C19—C20	1.369 (8)
N2—C7	1.370 (6)	C19—H19	0.9500
N2—C6	1.433 (5)	C20—C21	1.393 (10)
N2—C17	1.475 (5)	C20—H20	0.9500
N3—N4	1.320 (6)	C21—C22	1.344 (10)
N3—C25	1.356 (6)	C21—H21	0.9500
N4—N5	1.334 (6)	C22—C23	1.368 (9)
N5—C26	1.339 (6)	C22—H22	0.9500
N5—C27	1.469 (6)	C23—H23	0.9500
C1—C2	1.394 (6)	C24—C25	1.482 (6)
C1—C6	1.409 (6)	C24—H24A	0.9900
C2—C3	1.386 (7)	C24—H24B	0.9900
C2—H2	0.9500	C25—C26	1.367 (6)
C3—C4	1.374 (7)	C26—H26	0.9500
C3—H3	0.9500	C27—C28	1.513 (7)
C4—C5	1.384 (7)	C27—H27A	0.9900
C4—H4	0.9500	C27—H27B	0.9900
C5—C6	1.399 (6)	C28—C29	1.453 (7)
C5—H5	0.9500	C28—H28A	0.9900
C7—C8	1.519 (6)	C28—H28B	0.9900
C8—C9	1.519 (6)	C29—C30	1.569 (7)
C8—C24	1.535 (6)	C29—H29A	0.9900
C8—H8	1.0000	C29—H29B	0.9900
C10—C11	1.520 (6)	C30—C31	1.508 (7)
C10—H10A	0.9900	C30—H30A	0.9900
C10—H10B	0.9900	C30—H30B	0.9900
C11—C16	1.382 (6)	C31—C32	1.520 (7)
C11—C12	1.395 (6)	C31—H31A	0.9900
C12—C13	1.389 (6)	C31—H31B	0.9900
C12—H12	0.9500	C32—C33	1.541 (7)
C13—C14	1.382 (8)	C32—H32A	0.9900
C13—H13	0.9500	C32—H32B	0.9900
C14—C15	1.376 (8)	C33—C34	1.462 (9)
C14—H14	0.9500	C33—H33A	0.9900
C15—C16	1.382 (7)	C33—H33B	0.9900
C15—H15	0.9500	C34—H34A	0.9800
C16—H16	0.9500	C34—H34B	0.9800
C17—C18	1.512 (6)	C34—H34C	0.9800

C9—N1—C1	124.2 (3)	C20—C19—H19	119.4
C9—N1—C10	117.5 (4)	C18—C19—H19	119.4
C1—N1—C10	118.3 (4)	C19—C20—C21	119.2 (6)
C7—N2—C6	122.8 (3)	C19—C20—H20	120.4
C7—N2—C17	118.4 (3)	C21—C20—H20	120.4
C6—N2—C17	118.1 (3)	C22—C21—C20	119.8 (6)
N4—N3—C25	109.0 (4)	C22—C21—H21	120.1
N3—N4—N5	107.1 (4)	C20—C21—H21	120.1
N4—N5—C26	110.8 (4)	C21—C22—C23	120.8 (6)
N4—N5—C27	119.8 (5)	C21—C22—H22	119.6
C26—N5—C27	129.4 (5)	C23—C22—H22	119.6
C2—C1—C6	119.0 (4)	C22—C23—C18	121.3 (6)
C2—C1—N1	119.2 (4)	C22—C23—H23	119.4
C6—C1—N1	121.7 (4)	C18—C23—H23	119.4
C3—C2—C1	120.8 (4)	C25—C24—C8	113.0 (4)
C3—C2—H2	119.6	C25—C24—H24A	109.0
C1—C2—H2	119.6	C8—C24—H24A	109.0
C4—C3—C2	120.2 (5)	C25—C24—H24B	109.0
C4—C3—H3	119.9	C8—C24—H24B	109.0
C2—C3—H3	119.9	H24A—C24—H24B	107.8
C3—C4—C5	120.1 (4)	N3—C25—C26	107.5 (4)
C3—C4—H4	119.9	N3—C25—C24	122.2 (4)
C5—C4—H4	119.9	C26—C25—C24	130.2 (4)
C4—C5—C6	120.8 (4)	N5—C26—C25	105.5 (4)
C4—C5—H5	119.6	N5—C26—H26	127.2
C6—C5—H5	119.6	C25—C26—H26	127.2
C5—C6—C1	119.0 (4)	N5—C27—C28	114.8 (5)
C5—C6—N2	119.0 (4)	N5—C27—H27A	108.6
C1—C6—N2	121.9 (4)	C28—C27—H27A	108.6
O2—C7—N2	122.2 (4)	N5—C27—H27B	108.6
O2—C7—C8	121.7 (4)	C28—C27—H27B	108.6
N2—C7—C8	116.1 (4)	H27A—C27—H27B	107.5
C7—C8—C9	105.1 (4)	C29—C28—C27	115.7 (6)
C7—C8—C24	110.8 (4)	C29—C28—H28A	108.4
C9—C8—C24	112.3 (4)	C27—C28—H28A	108.4
C7—C8—H8	109.5	C29—C28—H28B	108.4
C9—C8—H8	109.5	C27—C28—H28B	108.4
C24—C8—H8	109.5	H28A—C28—H28B	107.4
O1—C9—N1	122.4 (4)	C28—C29—C30	113.3 (6)
O1—C9—C8	122.6 (4)	C28—C29—H29A	108.9
N1—C9—C8	115.0 (4)	C30—C29—H29A	108.9
N1—C10—C11	116.0 (4)	C28—C29—H29B	108.9
N1—C10—H10A	108.3	C30—C29—H29B	108.9
C11—C10—H10A	108.3	H29A—C29—H29B	107.7
N1—C10—H10B	108.3	C31—C30—C29	115.4 (5)
C11—C10—H10B	108.3	C31—C30—H30A	108.4
H10A—C10—H10B	107.4	C29—C30—H30A	108.4
C16—C11—C12	118.9 (4)	C31—C30—H30B	108.4
C16—C11—C10	123.5 (4)	C29—C30—H30B	108.4
C12—C11—C10	117.6 (4)	H30A—C30—H30B	107.5
C13—C12—C11	120.1 (5)	C30—C31—C32	113.0 (5)
C13—C12—H12	119.9	C30—C31—H31A	109.0
C11—C12—H12	119.9	C32—C31—H31A	109.0
C14—C13—C12	120.4 (5)	C30—C31—H31B	109.0
C14—C13—H13	119.8	C32—C31—H31B	109.0
C12—C13—H13	119.8	H31A—C31—H31B	107.8
C15—C14—C13	119.2 (5)	C31—C32—C33	112.1 (5)
C15—C14—H14	120.4	C31—C32—H32A	109.2
C13—C14—H14	120.4	C33—C32—H32A	109.2
C14—C15—C16	120.9 (5)	C31—C32—H32B	109.2
C14—C15—H15	119.5	C33—C32—H32B	109.2
C16—C15—H15	119.5	H32A—C32—H32B	107.9
C15—C16—C11	120.4 (5)	C34—C33—C32	112.2 (6)
C15—C16—H16	119.8	C34—C33—H33A	109.2
C11—C16—H16	119.8	C32—C33—H33A	109.2
N2—C17—C18	113.5 (3)	C34—C33—H33B	109.2
N2—C17—H17A	108.9	C32—C33—H33B	109.2
C18—C17—H17A	108.9	H33A—C33—H33B	107.9
N2—C17—H17B	108.9	C33—C34—H34A	109.5
C18—C17—H17B	108.9	C33—C34—H34B	109.5
H17A—C17—H17B	107.7	H34A—C34—H34B	109.5
C23—C18—C19	117.7 (5)	C33—C34—H34C	109.5
C23—C18—C17	121.1 (4)	H34A—C34—H34C	109.5
C19—C18—C17	121.1 (4)	H34B—C34—H34C	109.5
C20—C19—C18	121.2 (6)

C25—N3—N4—N5	0.3 (7)	N1—C10—C11—C16	−5.8 (7)
N3—N4—N5—C26	0.7 (6)	N1—C10—C11—C12	175.1 (4)
N3—N4—N5—C27	−177.2 (5)	C16—C11—C12—C13	0.4 (7)
C9—N1—C1—C2	135.7 (5)	C10—C11—C12—C13	179.5 (4)
C10—N1—C1—C2	−44.3 (6)	C11—C12—C13—C14	−1.2 (8)
C9—N1—C1—C6	−45.7 (6)	C12—C13—C14—C15	0.6 (8)
C10—N1—C1—C6	134.4 (4)	C13—C14—C15—C16	0.9 (9)
C6—C1—C2—C3	−1.3 (7)	C14—C15—C16—C11	−1.6 (8)
N1—C1—C2—C3	177.3 (5)	C12—C11—C16—C15	1.0 (7)
C1—C2—C3—C4	0.5 (8)	C10—C11—C16—C15	−178.1 (5)
C2—C3—C4—C5	0.8 (8)	C7—N2—C17—C18	−127.1 (4)
C3—C4—C5—C6	−1.2 (7)	C6—N2—C17—C18	62.2 (5)
C4—C5—C6—C1	0.3 (7)	N2—C17—C18—C23	−121.0 (4)
C4—C5—C6—N2	−177.2 (5)	N2—C17—C18—C19	62.2 (6)
C2—C1—C6—C5	1.0 (7)	C23—C18—C19—C20	−1.9 (8)
N1—C1—C6—C5	−177.7 (4)	C17—C18—C19—C20	175.0 (5)
C2—C1—C6—N2	178.4 (4)	C18—C19—C20—C21	0.5 (10)
N1—C1—C6—N2	−0.3 (7)	C19—C20—C21—C22	1.3 (10)
C7—N2—C6—C5	−132.9 (5)	C20—C21—C22—C23	−1.7 (10)
C17—N2—C6—C5	37.4 (6)	C21—C22—C23—C18	0.2 (9)
C7—N2—C6—C1	49.7 (6)	C19—C18—C23—C22	1.6 (8)
C17—N2—C6—C1	−140.0 (4)	C17—C18—C23—C22	−175.3 (5)
C6—N2—C7—O2	175.4 (4)	C7—C8—C24—C25	−171.2 (4)
C17—N2—C7—O2	5.1 (7)	C9—C8—C24—C25	71.6 (5)
C6—N2—C7—C8	−7.1 (6)	N4—N3—C25—C26	−1.0 (7)
C17—N2—C7—C8	−177.3 (4)	N4—N3—C25—C24	175.9 (5)
O2—C7—C8—C9	106.5 (5)	C8—C24—C25—N3	66.7 (6)
N2—C7—C8—C9	−71.1 (5)	C8—C24—C25—C26	−117.1 (6)
O2—C7—C8—C24	−15.0 (6)	N4—N5—C26—C25	−1.3 (6)
N2—C7—C8—C24	167.4 (4)	C27—N5—C26—C25	176.3 (5)
C1—N1—C9—O1	177.8 (4)	N3—C25—C26—N5	1.4 (6)
C10—N1—C9—O1	−2.3 (6)	C24—C25—C26—N5	−175.2 (5)
C1—N1—C9—C8	−0.3 (6)	N4—N5—C27—C28	−73.6 (7)
C10—N1—C9—C8	179.7 (3)	C26—N5—C27—C28	109.0 (7)
C7—C8—C9—O1	−102.6 (5)	N5—C27—C28—C29	−56.3 (10)
C24—C8—C9—O1	17.9 (6)	C27—C28—C29—C30	−166.2 (6)
C7—C8—C9—N1	75.4 (5)	C28—C29—C30—C31	−58.8 (10)
C24—C8—C9—N1	−164.0 (4)	C29—C30—C31—C32	−166.2 (6)
C9—N1—C10—C11	−80.1 (5)	C30—C31—C32—C33	−172.4 (6)
C1—N1—C10—C11	99.9 (5)	C31—C32—C33—C34	170.1 (6)

Experimental details

Crystal data
Chemical formula	C₃₄H₃₉N₅O₂
M_r	549.70
Crystal system, space group	Orthorhombic, P2₁2₁2₁
Temperature (K)	193
a, b, c (Å)	9.1797 (2), 10.4238 (2), 31.4716 (7)
V (Å³)	3011.4 (1)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.08
Crystal size (mm)	0.30 × 0.16 × 0.10

Data collection
Diffractometer	Bruker APEXII diffractometer
Absorption correction	–
No. of measured, independent and observed [I > 2σ(I)] reflections	44767, 3027, 2307
R_int	0.072
(sin θ/λ)_max (Å⁻¹)	0.595

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.057, 0.174, 1.02
No. of reflections	3027
No. of parameters	370
No. of restraints	59
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.59, −0.41
Absolute structure	Friedel pairs were merged

Computer programs: APEX2 (Bruker, 2005), SAINT (Bruker, 2005), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), X-SEED (Barbour, 2001), publCIF (Westrip, 2010).

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
Jabli, H., Kandri Rodi, Y., Ladeira, S., Essassi, E. M. & Ng, S. W. (2010). Acta Cryst. E66, o126. 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
Westrip, S. P. (2010). publCIF. In preparation. Google Scholar

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