5,5′′-Dibromo-1,1′′-bis­(prop-2-en-1-yl)-1,1′′,2,2′′-tetra­hydro­dispiro­[indole-3,7′-[6,9]diaza­tricyclo­[7.3.0.02,6]dodecane-8′,3′′-indole]-2,2′′-dione

Al Mamari, K.; Ennajih, H.; Bouhfid, R.; Essassi, E.M.; Ng, S.W.

doi:10.1107/S1600536812019228

organic compounds

CRYSTALLOGRAPHIC
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ISSN: 2056-9890

Volume 68| Part 6| June 2012| Page o1638

doi:10.1107/S1600536812019228

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5,5′′-Dibromo-1,1′′-bis(prop-2-en-1-yl)-1,1′′,2,2′′-tetrahydrodispiro[indole-3,7′-[6,9]diazatricyclo[7.3.0.0^2,6]dodecane-8′,3′′-indole]-2,2′′-dione

Khalil Al Mamari,^a Hamid Ennajih,^a Rachid Bouhfid,^b El Mokhtar Essassi ^a and Seik Weng Ng ^c,^d ^*

^aLaboratoire de Chimie Organique Hétérocyclique, Pôle de Compétences Pharmacochimie, Université Mohammed V–Agdal, BP 1014 Avenue Ibn Batout, Rabat, Morocco, ^bInstitute of Nanomaterials and Nanotechnology MAScIR, Avenue de l'Armée Royale, Rabat, Morocco, ^cDepartment of Chemistry, University of Malaya, 50603 Kuala Lumpur, Malaysia, and ^dChemistry Department, King Abdulaziz University, PO Box 80203 Jeddah, Saudi Arabia
^*Correspondence e-mail: seikweng@um.edu.my

(Received 28 April 2012; accepted 29 April 2012; online 5 May 2012)

In the molecule of the title compound, C₃₀H₃₀Br₂N₄O₂, the piperazine ring adopts a chair conformation. The pyrrolidine rings that are fused to the piperazine ring adopt envelope conformations (in which the N atom represents the flap). The indoline fused-ring systems are nearly planar (r.m.s. deviations = 0.009 and 0.019 Å); the two fused rings are aligned at 60.63 (6)°.

Related literature

For background to the class of dispiro compounds, see: Al Mamari et al. (2012a ). For a related structure, see: Al Mamari et al. (2012b ).

Experimental

Crystal data

C₃₀H₃₀Br₂N₄O₂
M_r = 638.40
Monoclinic, P 2₁ /c
a = 14.1658 (3) Å
b = 9.7203 (2) Å
c = 20.6677 (3) Å
β = 100.037 (1)°
V = 2802.30 (9) Å³
Z = 4
Mo Kα radiation
μ = 2.93 mm⁻¹
T = 293 K
0.30 × 0.28 × 0.26 mm

Data collection

Bruker APEX DUO diffractometer
Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ) T_min = 0.474, T_max = 0.517
31592 measured reflections
6671 independent reflections
4152 reflections with I > 2σ(I)
R_int = 0.050

Refinement

R[F² > 2σ(F²)] = 0.040
wR(F²) = 0.113
S = 0.96
6671 reflections
343 parameters
H-atom parameters constrained
Δρ_max = 0.54 e Å⁻³
Δρ_min = −0.61 e Å⁻³

Data collection: APEX2 (Bruker, 2010 ); cell refinement: SAINT (Bruker, 2010); 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/S1600536812019228/xu5528sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536812019228/xu5528Isup2.hkl

checkCIF report

Comment top

We reported the the 1,3-dipolar cycloaddition of 1-allyl-5-haloisatin derivatives as dipolarophiles with the azomethine ylides generated in situ from N-allylisatin and L-proline to yield dispiro-oxindoles (Al Mamari et al., 2012a). Although one of the reactants is optically active, the product, C₃₀H₃₀Br₂N₄O₂, crystallizes in a centrosymmetric space group, as does the bromo analog (Scheme I). However, the bromo analog is not isostructural; the two compounds have different cell dimensions. The piperazine ring adopts a chair conformation. The pyrrolidine rings that are fused to the piperazine ring adopt envelope conformations (in which the N atom represents the flap) (Fig. 1). The indoline fused-ring systems are nearly planar (r.m.s. deviation 0.009, 0.019 Å); the two fused-rings are aligned at 60.63 (6) °.

Related literature top

For background to the class of dispiro compounds, see: Al Mamari et al. (2012a). For a related structure, see: Al Mamari et al. (2012b).

Experimental top

A mixture of 1-allyl–5-bromo-indoline-2,3-dione (1 g, 0.005 mol) and proline (0.5 g, 0.004 mole) in ethanol (20 ml) was heated for 2 hours. On completion of the reaction as indicated by TLC, water (50 ml) was added. The precipitate was collected and recrystallized from ethanol to yield colorless crystals.

Computing details top

Data collection: APEX2 (Bruker, 2010); cell refinement: SAINT (Bruker, 2010); data reduction: SAINT (Bruker, 2010); 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. Thermal ellipsoid plot (Barbour, 2001) of C₃₀H₃₀Br₂N₄O₂ at the 50% probability level.

5,5''-Dibromo-1,1''-bis(prop-2-en-1-yl)-1,1'',2,2''-tetrahydrodispiro[indole- 3,7'-[6,9]diazatricyclo[7.3.0.0^2,6]dodecane-8',3''-indole]-2,2''-dione top

Crystal data top

C₃₀H₃₀Br₂N₄O₂	F(000) = 1296
M_r = 638.40	D_x = 1.513 Mg m⁻³
Monoclinic, P2₁/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 8234 reflections
a = 14.1658 (3) Å	θ = 2.3–24.1°
b = 9.7203 (2) Å	µ = 2.93 mm⁻¹
c = 20.6677 (3) Å	T = 293 K
β = 100.037 (1)°	Prism, colorless
V = 2802.30 (9) Å³	0.30 × 0.28 × 0.26 mm
Z = 4

Data collection top

Bruker APEX DUO diffractometer	6671 independent reflections
Radiation source: fine-focus sealed tube	4152 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.050
ω scans	θ_max = 27.9°, θ_min = 2.6°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −18→17
T_min = 0.474, T_max = 0.517	k = −9→12
31592 measured reflections	l = −27→27

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)] = 0.040	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.113	H-atom parameters constrained
S = 0.96	w = 1/[σ²(F_o²) + (0.0541P)² + 1.2207P] where P = (F_o² + 2F_c²)/3
6671 reflections	(Δ/σ)_max = 0.001
343 parameters	Δρ_max = 0.54 e Å⁻³
0 restraints	Δρ_min = −0.61 e Å⁻³

Crystal data top

C₃₀H₃₀Br₂N₄O₂	V = 2802.30 (9) Å³
M_r = 638.40	Z = 4
Monoclinic, P2₁/c	Mo Kα radiation
a = 14.1658 (3) Å	µ = 2.93 mm⁻¹
b = 9.7203 (2) Å	T = 293 K
c = 20.6677 (3) Å	0.30 × 0.28 × 0.26 mm
β = 100.037 (1)°

Data collection top

Bruker APEX DUO diffractometer	6671 independent reflections
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	4152 reflections with I > 2σ(I)
T_min = 0.474, T_max = 0.517	R_int = 0.050
31592 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.040	0 restraints
wR(F²) = 0.113	H-atom parameters constrained
S = 0.96	Δρ_max = 0.54 e Å⁻³
6671 reflections	Δρ_min = −0.61 e Å⁻³
343 parameters

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

	x	y	z	U_iso*/U_eq
Br1	0.58304 (2)	0.77248 (4)	0.418209 (16)	0.06146 (13)
Br2	0.21952 (4)	0.00640 (4)	0.46489 (2)	0.09482 (18)
O1	0.07667 (13)	0.4625 (2)	0.35513 (9)	0.0494 (5)
O2	0.36870 (13)	0.5244 (2)	0.22067 (9)	0.0453 (5)
C1	0.29680 (18)	0.5642 (3)	0.44015 (12)	0.0359 (6)
C2	0.3608 (2)	0.5972 (3)	0.49586 (13)	0.0512 (8)
H2	0.3468	0.5796	0.5374	0.061*
C3	0.4470 (2)	0.6575 (3)	0.48829 (14)	0.0504 (7)
H3	0.4923	0.6797	0.5250	0.061*
C4	0.46540 (18)	0.6846 (3)	0.42628 (13)	0.0411 (6)
C5	0.40107 (17)	0.6518 (3)	0.37021 (12)	0.0340 (6)
H5	0.4145	0.6719	0.3288	0.041*
C6	0.31608 (16)	0.5884 (2)	0.37742 (11)	0.0301 (5)
C7	0.23255 (17)	0.5410 (3)	0.32613 (12)	0.0308 (5)
C8	0.15937 (18)	0.4978 (3)	0.37166 (13)	0.0351 (6)
C9	0.1613 (2)	0.4637 (3)	0.49103 (14)	0.0476 (7)
H9A	0.2106	0.4221	0.5236	0.057*
H9B	0.1142	0.3931	0.4759	0.057*
C10	0.1140 (2)	0.5741 (4)	0.52322 (14)	0.0525 (8)
H10	0.0930	0.5513	0.5621	0.063*
C11	0.0991 (3)	0.6987 (4)	0.50244 (18)	0.0718 (10)
H11A	0.1188	0.7263	0.4638	0.086*
H11B	0.0687	0.7610	0.5261	0.086*
C12	0.1692 (2)	0.7781 (3)	0.30457 (15)	0.0487 (7)
H12A	0.2250	0.8309	0.3243	0.058*
H12B	0.1281	0.7640	0.3370	0.058*
C13	0.1150 (3)	0.8498 (4)	0.24315 (16)	0.0647 (9)
H13A	0.0556	0.8892	0.2520	0.078*
H13B	0.1537	0.9229	0.2294	0.078*
C14	0.0943 (2)	0.7407 (3)	0.19024 (16)	0.0561 (8)
H14A	0.1349	0.7528	0.1574	0.067*
H14B	0.0277	0.7438	0.1689	0.067*
C15	0.11682 (18)	0.6059 (3)	0.22698 (13)	0.0401 (6)
H15	0.0620	0.5774	0.2468	0.048*
C16	0.14914 (19)	0.4891 (3)	0.18941 (13)	0.0407 (6)
H16	0.2029	0.5189	0.1687	0.049*
C17	0.0744 (2)	0.4164 (4)	0.13854 (15)	0.0578 (8)
H17A	0.0115	0.4209	0.1509	0.069*
H17B	0.0712	0.4578	0.0955	0.069*
C18	0.1094 (3)	0.2683 (4)	0.13855 (19)	0.0803 (12)
H18A	0.0586	0.2052	0.1446	0.096*
H18B	0.1298	0.2469	0.0973	0.096*
C19	0.1929 (2)	0.2564 (3)	0.19506 (16)	0.0566 (8)
H19A	0.1897	0.1714	0.2192	0.068*
H19B	0.2537	0.2603	0.1795	0.068*
C20	0.35499 (18)	0.4387 (3)	0.26056 (13)	0.0356 (6)
C21	0.26015 (17)	0.4105 (2)	0.28799 (12)	0.0339 (6)
C22	0.29012 (19)	0.2894 (3)	0.33298 (13)	0.0398 (6)
C23	0.2387 (2)	0.2126 (3)	0.37111 (15)	0.0494 (7)
H23	0.1746	0.2315	0.3721	0.059*
C24	0.2863 (3)	0.1059 (3)	0.40796 (15)	0.0590 (9)
C25	0.3796 (3)	0.0721 (3)	0.40497 (17)	0.0662 (10)
H25	0.4086	−0.0010	0.4298	0.079*
C26	0.4307 (2)	0.1456 (3)	0.36554 (16)	0.0586 (8)
H26	0.4936	0.1226	0.3627	0.070*
C27	0.3849 (2)	0.2546 (3)	0.33049 (14)	0.0428 (7)
C28	0.5159 (2)	0.3350 (4)	0.26852 (15)	0.0544 (8)
H28A	0.5108	0.3652	0.2233	0.065*
H28B	0.5363	0.2396	0.2706	0.065*
C29	0.5904 (2)	0.4189 (5)	0.31056 (19)	0.0817 (12)
H29	0.5719	0.5061	0.3220	0.098*
C30	0.6727 (3)	0.3861 (7)	0.3315 (2)	0.133 (2)
H30A	0.6950	0.3001	0.3215	0.159*
H30B	0.7135	0.4470	0.3575	0.159*
N1	0.20466 (15)	0.5078 (2)	0.43570 (11)	0.0387 (5)
N2	0.19727 (14)	0.6467 (2)	0.27880 (10)	0.0334 (5)
N3	0.18063 (14)	0.3764 (2)	0.23592 (10)	0.0381 (5)
N4	0.42146 (16)	0.3437 (2)	0.28745 (11)	0.0430 (5)

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Br1	0.03869 (17)	0.0799 (3)	0.0637 (2)	−0.02284 (15)	0.00310 (14)	−0.00209 (17)
Br2	0.1388 (4)	0.0657 (3)	0.0792 (3)	−0.0361 (2)	0.0167 (3)	0.0224 (2)
O1	0.0349 (10)	0.0619 (13)	0.0521 (12)	−0.0160 (9)	0.0098 (9)	−0.0044 (10)
O2	0.0421 (11)	0.0487 (12)	0.0479 (11)	−0.0025 (9)	0.0156 (9)	0.0003 (10)
C1	0.0338 (13)	0.0370 (15)	0.0373 (14)	−0.0030 (11)	0.0075 (11)	0.0020 (12)
C2	0.0512 (17)	0.070 (2)	0.0319 (14)	−0.0084 (15)	0.0054 (13)	0.0032 (14)
C3	0.0422 (16)	0.067 (2)	0.0381 (15)	−0.0104 (15)	−0.0034 (12)	−0.0031 (14)
C4	0.0318 (13)	0.0437 (16)	0.0468 (16)	−0.0067 (12)	0.0044 (12)	−0.0001 (13)
C5	0.0330 (13)	0.0355 (14)	0.0345 (13)	−0.0044 (11)	0.0087 (11)	0.0004 (11)
C6	0.0302 (12)	0.0298 (13)	0.0301 (12)	−0.0003 (10)	0.0048 (10)	−0.0022 (10)
C7	0.0290 (12)	0.0313 (13)	0.0330 (13)	−0.0028 (10)	0.0079 (10)	−0.0017 (11)
C8	0.0348 (14)	0.0328 (14)	0.0395 (14)	−0.0021 (11)	0.0113 (11)	−0.0021 (11)
C9	0.0464 (16)	0.0577 (19)	0.0410 (15)	−0.0092 (14)	0.0146 (13)	0.0076 (14)
C10	0.0531 (18)	0.067 (2)	0.0412 (16)	−0.0120 (16)	0.0201 (14)	−0.0020 (16)
C11	0.087 (3)	0.069 (3)	0.067 (2)	−0.007 (2)	0.037 (2)	−0.013 (2)
C12	0.0523 (17)	0.0370 (16)	0.0568 (18)	0.0086 (13)	0.0093 (14)	−0.0029 (14)
C13	0.081 (2)	0.053 (2)	0.062 (2)	0.0252 (18)	0.0178 (18)	0.0126 (17)
C14	0.0487 (17)	0.062 (2)	0.0545 (17)	0.0136 (15)	0.0004 (14)	0.0120 (16)
C15	0.0307 (13)	0.0494 (17)	0.0388 (14)	−0.0001 (12)	0.0020 (11)	0.0009 (13)
C16	0.0347 (14)	0.0507 (17)	0.0364 (14)	−0.0047 (12)	0.0057 (11)	−0.0035 (13)
C17	0.0502 (18)	0.080 (2)	0.0410 (16)	−0.0097 (17)	0.0022 (13)	−0.0119 (16)
C18	0.082 (3)	0.084 (3)	0.070 (2)	−0.011 (2)	−0.003 (2)	−0.039 (2)
C19	0.062 (2)	0.0503 (19)	0.0578 (19)	−0.0069 (15)	0.0118 (16)	−0.0219 (15)
C20	0.0343 (14)	0.0347 (15)	0.0384 (14)	−0.0005 (12)	0.0076 (11)	−0.0086 (12)
C21	0.0325 (13)	0.0300 (14)	0.0396 (14)	−0.0025 (11)	0.0071 (11)	−0.0034 (11)
C22	0.0470 (15)	0.0289 (14)	0.0437 (15)	−0.0013 (12)	0.0082 (12)	−0.0053 (12)
C23	0.0611 (19)	0.0333 (16)	0.0532 (17)	−0.0076 (14)	0.0086 (15)	−0.0010 (14)
C24	0.088 (3)	0.0355 (17)	0.0518 (18)	−0.0125 (17)	0.0087 (17)	0.0008 (14)
C25	0.098 (3)	0.0369 (19)	0.058 (2)	0.0124 (18)	−0.002 (2)	0.0019 (16)
C26	0.067 (2)	0.0466 (19)	0.0586 (19)	0.0157 (16)	−0.0003 (16)	−0.0007 (16)
C27	0.0491 (16)	0.0332 (15)	0.0447 (15)	0.0044 (12)	0.0040 (13)	−0.0086 (12)
C28	0.0423 (16)	0.071 (2)	0.0512 (17)	0.0166 (15)	0.0115 (14)	−0.0123 (16)
C29	0.043 (2)	0.123 (4)	0.081 (3)	0.004 (2)	0.0170 (18)	−0.035 (2)
C30	0.058 (3)	0.243 (7)	0.099 (3)	−0.011 (4)	0.018 (2)	−0.057 (4)
N1	0.0345 (12)	0.0471 (14)	0.0368 (12)	−0.0066 (10)	0.0124 (9)	0.0015 (10)
N2	0.0336 (11)	0.0312 (12)	0.0352 (11)	0.0019 (9)	0.0049 (9)	0.0003 (9)
N3	0.0362 (12)	0.0382 (13)	0.0394 (12)	−0.0048 (10)	0.0049 (10)	−0.0095 (10)
N4	0.0379 (12)	0.0431 (14)	0.0490 (13)	0.0069 (11)	0.0106 (10)	−0.0055 (11)

Geometric parameters (Å, º) top

Br1—C4	1.906 (3)	C15—N2	1.476 (3)
Br2—C24	1.898 (3)	C15—C16	1.492 (4)
O1—C8	1.212 (3)	C15—H15	0.9800
O2—C20	1.211 (3)	C16—N3	1.474 (3)
C1—C2	1.374 (4)	C16—C17	1.528 (4)
C1—C6	1.391 (3)	C16—H16	0.9800
C1—N1	1.404 (3)	C17—C18	1.523 (5)
C2—C3	1.388 (4)	C17—H17A	0.9700
C2—H2	0.9300	C17—H17B	0.9700
C3—C4	1.377 (4)	C18—C19	1.515 (5)
C3—H3	0.9300	C18—H18A	0.9700
C4—C5	1.381 (3)	C18—H18B	0.9700
C5—C6	1.384 (3)	C19—N3	1.468 (3)
C5—H5	0.9300	C19—H19A	0.9700
C6—C7	1.516 (3)	C19—H19B	0.9700
C7—N2	1.446 (3)	C20—N4	1.365 (3)
C7—C8	1.574 (3)	C20—C21	1.571 (3)
C7—C21	1.578 (3)	C21—N3	1.454 (3)
C8—N1	1.370 (3)	C21—C22	1.514 (4)
C9—N1	1.454 (3)	C22—C23	1.382 (4)
C9—C10	1.482 (4)	C22—C27	1.394 (4)
C9—H9A	0.9700	C23—C24	1.390 (4)
C9—H9B	0.9700	C23—H23	0.9300
C10—C11	1.291 (5)	C24—C25	1.373 (5)
C10—H10	0.9300	C25—C26	1.380 (5)
C11—H11A	0.9300	C25—H25	0.9300
C11—H11B	0.9300	C26—C27	1.380 (4)
C12—N2	1.466 (3)	C26—H26	0.9300
C12—C13	1.532 (4)	C27—N4	1.404 (4)
C12—H12A	0.9700	C28—N4	1.461 (3)
C12—H12B	0.9700	C28—C29	1.488 (5)
C13—C14	1.515 (5)	C28—H28A	0.9700
C13—H13A	0.9700	C28—H28B	0.9700
C13—H13B	0.9700	C29—C30	1.214 (6)
C14—C15	1.520 (4)	C29—H29	0.9300
C14—H14A	0.9700	C30—H30A	0.9300
C14—H14B	0.9700	C30—H30B	0.9300

C2—C1—C6	122.3 (2)	C18—C17—C16	104.5 (3)
C2—C1—N1	128.0 (2)	C18—C17—H17A	110.8
C6—C1—N1	109.7 (2)	C16—C17—H17A	110.8
C1—C2—C3	118.0 (3)	C18—C17—H17B	110.8
C1—C2—H2	121.0	C16—C17—H17B	110.8
C3—C2—H2	121.0	H17A—C17—H17B	108.9
C4—C3—C2	119.9 (3)	C19—C18—C17	106.4 (3)
C4—C3—H3	120.1	C19—C18—H18A	110.4
C2—C3—H3	120.1	C17—C18—H18A	110.4
C3—C4—C5	122.2 (2)	C19—C18—H18B	110.4
C3—C4—Br1	118.5 (2)	C17—C18—H18B	110.4
C5—C4—Br1	119.3 (2)	H18A—C18—H18B	108.6
C4—C5—C6	118.1 (2)	N3—C19—C18	103.2 (3)
C4—C5—H5	120.9	N3—C19—H19A	111.1
C6—C5—H5	120.9	C18—C19—H19A	111.1
C5—C6—C1	119.5 (2)	N3—C19—H19B	111.1
C5—C6—C7	130.4 (2)	C18—C19—H19B	111.1
C1—C6—C7	110.1 (2)	H19A—C19—H19B	109.1
N2—C7—C6	113.1 (2)	O2—C20—N4	124.1 (2)
N2—C7—C8	114.1 (2)	O2—C20—C21	127.9 (2)
C6—C7—C8	100.27 (19)	N4—C20—C21	107.9 (2)
N2—C7—C21	108.64 (19)	N3—C21—C22	112.1 (2)
C6—C7—C21	111.26 (19)	N3—C21—C20	111.9 (2)
C8—C7—C21	109.31 (19)	C22—C21—C20	101.0 (2)
O1—C8—N1	124.0 (2)	N3—C21—C7	108.97 (19)
O1—C8—C7	127.8 (2)	C22—C21—C7	112.7 (2)
N1—C8—C7	108.2 (2)	C20—C21—C7	109.99 (19)
N1—C9—C10	115.2 (3)	C23—C22—C27	119.8 (3)
N1—C9—H9A	108.5	C23—C22—C21	130.6 (3)
C10—C9—H9A	108.5	C27—C22—C21	109.5 (2)
N1—C9—H9B	108.5	C22—C23—C24	117.5 (3)
C10—C9—H9B	108.5	C22—C23—H23	121.3
H9A—C9—H9B	107.5	C24—C23—H23	121.3
C11—C10—C9	126.2 (3)	C25—C24—C23	122.2 (3)
C11—C10—H10	116.9	C25—C24—Br2	119.6 (3)
C9—C10—H10	116.9	C23—C24—Br2	118.2 (3)
C10—C11—H11A	120.0	C24—C25—C26	120.7 (3)
C10—C11—H11B	120.0	C24—C25—H25	119.6
H11A—C11—H11B	120.0	C26—C25—H25	119.6
N2—C12—C13	102.9 (2)	C25—C26—C27	117.4 (3)
N2—C12—H12A	111.2	C25—C26—H26	121.3
C13—C12—H12A	111.2	C27—C26—H26	121.3
N2—C12—H12B	111.2	C26—C27—C22	122.4 (3)
C13—C12—H12B	111.2	C26—C27—N4	127.9 (3)
H12A—C12—H12B	109.1	C22—C27—N4	109.7 (2)
C14—C13—C12	106.6 (2)	N4—C28—C29	113.7 (2)
C14—C13—H13A	110.4	N4—C28—H28A	108.8
C12—C13—H13A	110.4	C29—C28—H28A	108.8
C14—C13—H13B	110.4	N4—C28—H28B	108.8
C12—C13—H13B	110.4	C29—C28—H28B	108.8
H13A—C13—H13B	108.6	H28A—C28—H28B	107.7
C13—C14—C15	104.2 (2)	C30—C29—C28	127.1 (5)
C13—C14—H14A	110.9	C30—C29—H29	116.4
C15—C14—H14A	110.9	C28—C29—H29	116.4
C13—C14—H14B	110.9	C29—C30—H30A	120.0
C15—C14—H14B	110.9	C29—C30—H30B	120.0
H14A—C14—H14B	108.9	H30A—C30—H30B	120.0
N2—C15—C16	108.3 (2)	C8—N1—C1	111.4 (2)
N2—C15—C14	101.5 (2)	C8—N1—C9	123.2 (2)
C16—C15—C14	116.9 (2)	C1—N1—C9	125.4 (2)
N2—C15—H15	109.9	C7—N2—C12	117.2 (2)
C16—C15—H15	109.9	C7—N2—C15	115.6 (2)
C14—C15—H15	109.9	C12—N2—C15	105.9 (2)
N3—C16—C15	108.1 (2)	C21—N3—C19	116.9 (2)
N3—C16—C17	101.5 (2)	C21—N3—C16	114.9 (2)
C15—C16—C17	118.1 (2)	C19—N3—C16	105.5 (2)
N3—C16—H16	109.5	C20—N4—C27	111.7 (2)
C15—C16—H16	109.5	C20—N4—C28	122.0 (2)
C17—C16—H16	109.5	C27—N4—C28	126.2 (2)

C6—C1—C2—C3	0.4 (4)	C27—C22—C23—C24	2.7 (4)
N1—C1—C2—C3	−177.4 (3)	C21—C22—C23—C24	−179.9 (3)
C1—C2—C3—C4	1.1 (5)	C22—C23—C24—C25	−3.0 (5)
C2—C3—C4—C5	−1.0 (5)	C22—C23—C24—Br2	176.1 (2)
C2—C3—C4—Br1	178.2 (2)	C23—C24—C25—C26	1.2 (5)
C3—C4—C5—C6	−0.7 (4)	Br2—C24—C25—C26	−178.0 (2)
Br1—C4—C5—C6	−179.82 (19)	C24—C25—C26—C27	1.0 (5)
C4—C5—C6—C1	2.2 (4)	C25—C26—C27—C22	−1.2 (4)
C4—C5—C6—C7	179.8 (2)	C25—C26—C27—N4	−179.9 (3)
C2—C1—C6—C5	−2.1 (4)	C23—C22—C27—C26	−0.6 (4)
N1—C1—C6—C5	176.1 (2)	C21—C22—C27—C26	−178.5 (3)
C2—C1—C6—C7	179.8 (3)	C23—C22—C27—N4	178.3 (2)
N1—C1—C6—C7	−2.0 (3)	C21—C22—C27—N4	0.4 (3)
C5—C6—C7—N2	−51.2 (3)	N4—C28—C29—C30	138.3 (5)
C1—C6—C7—N2	126.6 (2)	O1—C8—N1—C1	−174.0 (2)
C5—C6—C7—C8	−173.1 (3)	C7—C8—N1—C1	5.4 (3)
C1—C6—C7—C8	4.7 (3)	O1—C8—N1—C9	6.4 (4)
C5—C6—C7—C21	71.4 (3)	C7—C8—N1—C9	−174.2 (2)
C1—C6—C7—C21	−110.8 (2)	C2—C1—N1—C8	175.8 (3)
N2—C7—C8—O1	52.2 (3)	C6—C1—N1—C8	−2.3 (3)
C6—C7—C8—O1	173.4 (3)	C2—C1—N1—C9	−4.6 (4)
C21—C7—C8—O1	−69.6 (3)	C6—C1—N1—C9	177.3 (2)
N2—C7—C8—N1	−127.2 (2)	C10—C9—N1—C8	−96.0 (3)
C6—C7—C8—N1	−6.0 (3)	C10—C9—N1—C1	84.5 (3)
C21—C7—C8—N1	111.0 (2)	C6—C7—N2—C12	−54.9 (3)
N1—C9—C10—C11	8.1 (5)	C8—C7—N2—C12	58.9 (3)
N2—C12—C13—C14	14.0 (3)	C21—C7—N2—C12	−178.9 (2)
C12—C13—C14—C15	12.4 (3)	C6—C7—N2—C15	179.1 (2)
C13—C14—C15—N2	−33.9 (3)	C8—C7—N2—C15	−67.1 (3)
C13—C14—C15—C16	−151.5 (3)	C21—C7—N2—C15	55.1 (2)
N2—C15—C16—N3	57.9 (3)	C13—C12—N2—C7	−167.2 (2)
C14—C15—C16—N3	171.7 (2)	C13—C12—N2—C15	−36.6 (3)
N2—C15—C16—C17	172.4 (2)	C16—C15—N2—C7	−60.2 (3)
C14—C15—C16—C17	−73.9 (3)	C14—C15—N2—C7	176.2 (2)
N3—C16—C17—C18	−30.9 (3)	C16—C15—N2—C12	168.2 (2)
C15—C16—C17—C18	−148.9 (3)	C14—C15—N2—C12	44.6 (3)
C16—C17—C18—C19	7.9 (4)	C22—C21—N3—C19	−54.2 (3)
C17—C18—C19—N3	18.3 (4)	C20—C21—N3—C19	58.5 (3)
O2—C20—C21—N3	58.6 (3)	C7—C21—N3—C19	−179.6 (2)
N4—C20—C21—N3	−118.6 (2)	C22—C21—N3—C16	−178.7 (2)
O2—C20—C21—C22	178.0 (3)	C20—C21—N3—C16	−66.0 (3)
N4—C20—C21—C22	0.8 (2)	C7—C21—N3—C16	55.9 (3)
O2—C20—C21—C7	−62.7 (3)	C18—C19—N3—C21	−168.3 (3)
N4—C20—C21—C7	120.1 (2)	C18—C19—N3—C16	−39.2 (3)
N2—C7—C21—N3	−50.1 (2)	C15—C16—N3—C21	−60.8 (3)
C6—C7—C21—N3	−175.23 (19)	C17—C16—N3—C21	174.3 (2)
C8—C7—C21—N3	75.0 (2)	C15—C16—N3—C19	169.0 (2)
N2—C7—C21—C22	−175.15 (19)	C17—C16—N3—C19	44.0 (3)
C6—C7—C21—C22	59.7 (3)	O2—C20—N4—C27	−178.0 (2)
C8—C7—C21—C22	−50.1 (3)	C21—C20—N4—C27	−0.6 (3)
N2—C7—C21—C20	73.0 (2)	O2—C20—N4—C28	−1.8 (4)
C6—C7—C21—C20	−52.2 (3)	C21—C20—N4—C28	175.6 (2)
C8—C7—C21—C20	−162.0 (2)	C26—C27—N4—C20	179.0 (3)
N3—C21—C22—C23	−59.0 (4)	C22—C27—N4—C20	0.2 (3)
C20—C21—C22—C23	−178.3 (3)	C26—C27—N4—C28	3.0 (4)
C7—C21—C22—C23	64.4 (4)	C22—C27—N4—C28	−175.8 (2)
N3—C21—C22—C27	118.6 (2)	C29—C28—N4—C20	91.7 (4)
C20—C21—C22—C27	−0.7 (3)	C29—C28—N4—C27	−92.6 (4)
C7—C21—C22—C27	−118.0 (2)

Experimental details

Crystal data
Chemical formula	C₃₀H₃₀Br₂N₄O₂
M_r	638.40
Crystal system, space group	Monoclinic, P2₁/c
Temperature (K)	293
a, b, c (Å)	14.1658 (3), 9.7203 (2), 20.6677 (3)
β (°)	100.037 (1)
V (Å³)	2802.30 (9)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	2.93
Crystal size (mm)	0.30 × 0.28 × 0.26

Data collection
Diffractometer	Bruker APEX DUO diffractometer
Absorption correction	Multi-scan (SADABS; Sheldrick, 1996)
T_min, T_max	0.474, 0.517
No. of measured, independent and observed [I > 2σ(I)] reflections	31592, 6671, 4152
R_int	0.050
(sin θ/λ)_max (Å⁻¹)	0.658

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.040, 0.113, 0.96
No. of reflections	6671
No. of parameters	343
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.54, −0.61

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

Acknowledgements

We thank Université Mohammed V-Agdal, and the Ministry of Higher Education of Malaysia (grant No. UM.C/HIR/MOHE/SC/12) for supporting this study.

References

Al Mamari, K., Ennajih, H., Bouhfid, R., Essassi, E. M. & Ng, S. W. (2012b). Acta Cryst. E68, o1637. CSD CrossRef IUCr Journals Google Scholar
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