N-(2-Bromo­benz­yl)-2,6-diisopropyl­aniline

Cristea, A.; Varga, R.A.; Silvestru, C.

doi:10.1107/S1600536807052907

N-(2-Bromobenzyl)-2,6-diisopropylaniline

A. Cristea, R. A. Varga and C. Silvestru

The asymmetric unit of the title compound, C₁₉H₂₄BrN, contains two independent molecules that are linked into chains through intermolecular Br

H (3.06 Å) and H

phenyl contacts (3.15 Å). Furthermore, even stronger H

phenyl contacts (2.71–3.14 Å) between the chains and four neighbouring molecules result in a three-dimensional supramolecular architecture.

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Supporting information

	Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536807052907/pv2038sup1.cif Contains datablocks I, global
	Structure factor file (CIF format) https://doi.org/10.1107/S1600536807052907/pv2038Isup2.hkl Contains datablock I

CCDC reference: 672806

checkCIF report

Key indicators

Single-crystal X-ray study
T = 297 K
Mean (C-C) = 0.005 Å
R factor = 0.047
wR factor = 0.134
Data-to-parameter ratio = 18.2

checkCIF/PLATON results

No syntax errors found



Alert level B
PLAT148_ALERT_3_B su on the      b  - Axis is Too Large (x 1000) .         15 Ang.
PLAT148_ALERT_3_B su on the      c  - Axis is Too Large (x 1000) .         14 Ang.
PLAT220_ALERT_2_B Large Non-Solvent    C     Ueq(max)/Ueq(min) ...       3.66 Ratio
PLAT242_ALERT_2_B Check Low       Ueq as Compared to Neighbors for        C33

Alert level C
PLAT220_ALERT_2_C Large Non-Solvent    C     Ueq(max)/Ueq(min) ...       3.05 Ratio
PLAT222_ALERT_3_C Large Non-Solvent    H     Ueq(max)/Ueq(min) ...       3.38 Ratio
PLAT222_ALERT_3_C Large Non-Solvent    H     Ueq(max)/Ueq(min) ...       3.77 Ratio
PLAT242_ALERT_2_C Check Low       Ueq as Compared to Neighbors for        C14
PLAT242_ALERT_2_C Check Low       Ueq as Compared to Neighbors for        C17
PLAT242_ALERT_2_C Check Low       Ueq as Compared to Neighbors for        C36
PLAT414_ALERT_2_C Short Intra D-H..H-X       H1     ..  H14     ..       1.91 Ang.
PLAT414_ALERT_2_C Short Intra D-H..H-X       H2     ..  H22     ..       1.95 Ang.
PLAT420_ALERT_2_C D-H Without Acceptor       N1     -   H1     ...          ?
PLAT420_ALERT_2_C D-H Without Acceptor       N2     -   H2     ...          ?
PLAT480_ALERT_4_C Long H...A H-Bond Reported H18C   ..  BR2     ..       3.06 Ang.

Alert level G
PLAT860_ALERT_3_G Note: Number of Least-Squares Restraints .......          2

   0 ALERT level A = In general: serious problem
   4 ALERT level B = Potentially serious problem
  11 ALERT level C = Check and explain
   1 ALERT level G = General alerts; check

   0 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
  10 ALERT type 2 Indicator that the structure model may be wrong or deficient
   5 ALERT type 3 Indicator that the structure quality may be low
   1 ALERT type 4 Improvement, methodology, query or suggestion
   0 ALERT type 5 Informative message, check

Comment top

Our interest in hypervalent organometalic compounds with aryl groups containing pendant arms with N atoms able to stabilize unusual species through intramolecular coordination to a metal atom (Balazs et al., 2003, 2004, 2006; Opris et al., 2004; Fernández et al., 2007; Soran et al., 2007; Kulcsar et al., 2007; Rotar et al., 2007) prompted us to design new organic molecules with steric hinderence. In this paper, we present the structure of the title compound, (I).

The asymmetric unit of (I) contains two independent molecules A and B (A containing Br1 and B conatining Br2, respectively) which are chemically identical, but differ slightly in their conformations (Fig. 1). The most importand difference is the value of the dihedral angle between the planes passing through the phenyl rings of the molecules [78 (1)° for A and 89 (1)° for B].

The two molecules are linked into a chain by a weak intermoleculare interaction (Br2···H18C 3.06 Å) and a H···phenyl contact (H4···Cg3 = 3.15 Å). These chains interact further through other four H···phenyl interactions (H···π range 2.71–3.14 Å, see Extra Table) (Fig.2), resulting in a three-dimensional supramolecular arhitecture.

Related literature top

For related literature see Balazs et al. (2003, 2004, 2006); Opris et al. (2004); Fernández et al. (2007); Soran et al. (2007); Kulcsar et al. (2007); Rotar et al. (2007).

Experimental top

(2-Bromobezyl)-(2,6-diisopropylbenzyl)-amine was prepared from the reaction of brombenzyl-bromide and 2,6-diisopropilaniline in 1:1 molar ratio, in CH₃CN in the presence of K₂CO₃. The mixture was refluxed for 48 h. The solvent was removed in vacuo and the solid residue was extracted with ethanol. Crystals suitable for single-crystal X-ray diffraction were obtained from ethanol.

Computing details top

Data collection: SMART (Bruker, 2000); cell refinement: SMART (Bruker, 2000); data reduction: SAINT-Plus (Bruker, 2000); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXTL (Bruker, 2001); molecular graphics: DIAMOND (Brandenburg, 2006); software used to prepare material for publication: publCIF (Westrip, 2007).

Figures top

	Fig. 1. A view of the title compound showing two molecules in the asymmetric unit with the atomic-numbering scheme; displacement ellipsoids are drawn at the 30% probability level.
	Fig. 2. Intermolecular interactions in the crystal structure of the title compound. Symmetry codes: (i) x, 1/2 - y, -1/2 + z, (ii) 1 - x, 1 - y, -z, (iii) 1 - x, 1/2 + y, 1/2 - z, (iv) -x, -1/2 + y, 1/2 - z

N-(2-Bromobenzyl)-2,6-diisopropylaniline top

Crystal data top

C₁₉H₂₄BrN	F(000) = 1440
M_r = 346.30	D_x = 1.312 Mg m⁻³
Monoclinic, P2₁/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 4084 reflections
a = 17.207 (17) Å	θ = 2.3–20.6°
b = 14.742 (15) Å	µ = 2.34 mm⁻¹
c = 13.870 (14) Å	T = 297 K
β = 94.650 (18)°	Block, yellow
V = 3507 (6) Å³	0.60 × 0.33 × 0.31 mm
Z = 8

Data collection top

Bruker SMART APEX CCD area-detector diffractometer	7183 independent reflections
Radiation source: fine-focus sealed tube	4220 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.058
ω and ϕ scans	θ_max = 26.4°, θ_min = 1.2°
Absorption correction: multi-scan (SADABS; Bruker 2001)	h = −21→21
T_min = 0.304, T_max = 0.483	k = −18→17
27700 measured reflections	l = −17→17

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)] = 0.047	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.134	H atoms treated by a mixture of independent and constrained refinement
S = 1.03	w = 1/[σ²(F_o²) + (0.0628P)²] where P = (F_o² + 2F_c²)/3
7183 reflections	(Δ/σ)_max = 0.001
395 parameters	Δρ_max = 0.36 e Å⁻³
2 restraints	Δρ_min = −0.33 e Å⁻³

Crystal data top

C₁₉H₂₄BrN	V = 3507 (6) Å³
M_r = 346.30	Z = 8
Monoclinic, P2₁/c	Mo Kα radiation
a = 17.207 (17) Å	µ = 2.34 mm⁻¹
b = 14.742 (15) Å	T = 297 K
c = 13.870 (14) Å	0.60 × 0.33 × 0.31 mm
β = 94.650 (18)°

Data collection top

Bruker SMART APEX CCD area-detector diffractometer	7183 independent reflections
Absorption correction: multi-scan (SADABS; Bruker 2001)	4220 reflections with I > 2σ(I)
T_min = 0.304, T_max = 0.483	R_int = 0.058
27700 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.047	2 restraints
wR(F²) = 0.134	H atoms treated by a mixture of independent and constrained refinement
S = 1.03	Δρ_max = 0.36 e Å⁻³
7183 reflections	Δρ_min = −0.33 e Å⁻³
395 parameters

Special details top

Experimental. Spectroscopic analysis: ¹H NMR (CDCl₃, 300 MHz): δ 7.59 (dd, 1H, H₃, ³J_HH = 8.97), 7.429 (dd, 1H, H5, ³J_HH = 6.7 Hz), 7.32 (d, 1H, H_5, ³J_HH = 7.5 Hz), 7.29 (d, 2H, H₆), 7.12(m, 1H, H₁₁), 4.12 (s, 2H, CH₂), 3.45 (s, 1H, NH), 3.06 (sept, 1H, CH(CH₃)₂, ³J = 6.85 Hz), 1.22 (d, 12 H, CH(CH₃)₂, ³J = 6.87 Hz); ¹³C NMR (CDCl₃, 75.47 MHz): 24,25 s [(CH₃)₂CH–]; 27,68 s [-CH(CH₃)₂]; 55,72 s [CH₂], 123,57 s [C₂]; 124,11 s [C_{10 + 12}]; 127,58 s [C₁₁]; 128,79 s [C₅]; 129,97 s [C₆]; 132,75 s [C₃]; 139,22 s [C₄]; 142,89 s [C₁]; 137,58 s [C_{9 + 13}]

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
Br1	0.08740 (3)	0.45571 (3)	0.59450 (3)	0.08102 (18)
Br2	0.27279 (3)	0.23566 (3)	0.17106 (3)	0.08471 (19)
C1	0.1518 (2)	0.4781 (2)	0.4920 (2)	0.0536 (9)
C2	0.14641 (17)	0.4235 (2)	0.4103 (2)	0.0451 (8)
C3	0.19723 (19)	0.4424 (2)	0.3403 (3)	0.0511 (8)
H3	0.1948	0.4073	0.2844	0.061*
C4	0.2511 (2)	0.5113 (2)	0.3510 (3)	0.0645 (10)
H4	0.2851	0.5219	0.3034	0.077*
C5	0.2545 (2)	0.5645 (3)	0.4324 (3)	0.0758 (12)
H5	0.2903	0.6118	0.4394	0.091*
C6	0.2059 (2)	0.5483 (2)	0.5032 (3)	0.0719 (11)
H6	0.2087	0.5840	0.5586	0.086*
C7	0.0881 (2)	0.3477 (2)	0.4003 (3)	0.0559 (9)
H7A	0.0918	0.3120	0.4592	0.067*
H7B	0.0360	0.3731	0.3921	0.067*
C8	0.05121 (19)	0.2092 (2)	0.3135 (2)	0.0476 (8)
C9	−0.0186 (2)	0.2083 (2)	0.2549 (3)	0.0534 (9)
C10	−0.0616 (2)	0.1296 (2)	0.2484 (3)	0.0618 (9)
H10	−0.1075	0.1278	0.2082	0.074*
C11	−0.0382 (2)	0.0542 (2)	0.2998 (3)	0.0638 (10)
H11	−0.0681	0.0016	0.2946	0.077*
C12	0.0298 (2)	0.0560 (2)	0.3593 (3)	0.0614 (9)
H12	0.0452	0.0047	0.3950	0.074*
C13	0.07529 (19)	0.1330 (2)	0.3665 (2)	0.0521 (8)
C14	−0.0486 (2)	0.2900 (3)	0.1966 (3)	0.0710 (11)
H14	−0.0119	0.3400	0.2111	0.085*
C15	−0.0516 (3)	0.2724 (3)	0.0888 (4)	0.1121 (18)
H15A	−0.0860	0.2225	0.0726	0.168*
H15B	−0.0002	0.2580	0.0710	0.168*
H15C	−0.0704	0.3256	0.0544	0.168*
C16	−0.1270 (3)	0.3199 (4)	0.2250 (5)	0.137 (2)
H16A	−0.1656	0.2759	0.2032	0.206*
H16B	−0.1400	0.3775	0.1959	0.206*
H16C	−0.1254	0.3253	0.2941	0.206*
C17	0.1525 (2)	0.1301 (3)	0.4277 (3)	0.0667 (10)
H17	0.1717	0.1925	0.4354	0.080*
C18	0.2125 (2)	0.0761 (3)	0.3792 (3)	0.0883 (13)
H18A	0.1977	0.0133	0.3772	0.132*
H18B	0.2623	0.0825	0.4150	0.132*
H18C	0.2157	0.0981	0.3145	0.132*
C19	0.1435 (3)	0.0919 (4)	0.5285 (3)	0.119 (2)
H19A	0.1085	0.1296	0.5612	0.178*
H19B	0.1934	0.0906	0.5647	0.178*
H19C	0.1228	0.0314	0.5229	0.178*
C20	0.33447 (19)	0.2507 (2)	0.0648 (2)	0.0488 (8)
C21	0.38118 (18)	0.3273 (2)	0.0587 (2)	0.0437 (7)
C22	0.4236 (2)	0.3337 (2)	−0.0213 (2)	0.0583 (9)
H22	0.4555	0.3839	−0.0280	0.070*
C23	0.4198 (3)	0.2671 (3)	−0.0916 (3)	0.0779 (12)
H23	0.4490	0.2726	−0.1449	0.093*
C24	0.3734 (2)	0.1936 (3)	−0.0826 (3)	0.0732 (11)
H24	0.3709	0.1488	−0.1300	0.088*
C25	0.3306 (2)	0.1846 (2)	−0.0050 (3)	0.0619 (10)
H25	0.2990	0.1341	0.0007	0.074*
C26	0.3839 (2)	0.3989 (2)	0.1358 (2)	0.0534 (8)
H26A	0.3317	0.4221	0.1414	0.064*
H26B	0.4020	0.3720	0.1973	0.064*
C27	0.43522 (19)	0.5466 (2)	0.1832 (2)	0.0481 (8)
C28	0.38287 (19)	0.6181 (2)	0.1681 (2)	0.0522 (8)
C29	0.3880 (2)	0.6892 (2)	0.2329 (3)	0.0674 (10)
H29	0.3539	0.7379	0.2237	0.081*
C30	0.4422 (3)	0.6892 (3)	0.3101 (3)	0.0753 (12)
H30	0.4450	0.7383	0.3524	0.090*
C31	0.4920 (2)	0.6186 (3)	0.3261 (3)	0.0705 (11)
H31	0.5280	0.6194	0.3799	0.085*
C32	0.4900 (2)	0.5453 (2)	0.2633 (3)	0.0565 (9)
C33	0.3235 (2)	0.6204 (3)	0.0810 (3)	0.0704 (11)
H33	0.3168	0.5578	0.0581	0.084*
C34	0.2454 (3)	0.6534 (6)	0.1035 (4)	0.161 (3)
H34A	0.2496	0.7146	0.1269	0.241*
H34B	0.2256	0.6154	0.1521	0.241*
H34C	0.2104	0.6515	0.0459	0.241*
C35	0.3519 (3)	0.6745 (4)	−0.0009 (3)	0.1128 (18)
H35A	0.3122	0.6761	−0.0536	0.169*
H35B	0.3980	0.6467	−0.0222	0.169*
H35C	0.3638	0.7352	0.0206	0.169*
C36	0.5474 (2)	0.4683 (3)	0.2809 (3)	0.0757 (12)
H36	0.5248	0.4147	0.2475	0.091*
C37	0.6232 (3)	0.4892 (4)	0.2376 (4)	0.1159 (18)
H37A	0.6135	0.4976	0.1691	0.174*
H37B	0.6589	0.4397	0.2500	0.174*
H37C	0.6454	0.5436	0.2662	0.174*
C38	0.5624 (3)	0.4441 (3)	0.3879 (4)	0.128 (2)
H38A	0.5928	0.3895	0.3943	0.191*
H38B	0.5135	0.4349	0.4152	0.191*
H38C	0.5903	0.4927	0.4213	0.191*
N1	0.10011 (18)	0.2884 (2)	0.3183 (2)	0.0568 (8)
N2	0.43507 (18)	0.47372 (19)	0.1151 (2)	0.0542 (7)
H2	0.428 (3)	0.482 (3)	0.0571 (15)	0.109 (18)*
H1	0.092 (2)	0.322 (2)	0.267 (2)	0.092 (15)*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Br1	0.0975 (4)	0.0830 (3)	0.0650 (3)	0.0026 (2)	0.0213 (2)	−0.0153 (2)
Br2	0.1145 (4)	0.0704 (3)	0.0735 (3)	−0.0334 (2)	0.0336 (3)	−0.0005 (2)
C1	0.057 (2)	0.0439 (19)	0.060 (2)	0.0026 (16)	0.0021 (17)	−0.0036 (16)
C2	0.0443 (19)	0.0374 (17)	0.053 (2)	0.0013 (14)	−0.0015 (15)	0.0014 (15)
C3	0.052 (2)	0.0438 (19)	0.056 (2)	−0.0004 (16)	0.0000 (16)	0.0046 (16)
C4	0.056 (2)	0.053 (2)	0.084 (3)	−0.0081 (18)	0.002 (2)	0.016 (2)
C5	0.071 (3)	0.056 (2)	0.098 (3)	−0.020 (2)	−0.005 (3)	0.000 (2)
C6	0.078 (3)	0.056 (2)	0.079 (3)	−0.007 (2)	−0.010 (2)	−0.015 (2)
C7	0.056 (2)	0.048 (2)	0.065 (2)	−0.0078 (16)	0.0126 (18)	−0.0139 (17)
C8	0.049 (2)	0.0422 (18)	0.053 (2)	−0.0100 (15)	0.0095 (17)	−0.0102 (15)
C9	0.054 (2)	0.0411 (19)	0.065 (2)	−0.0045 (16)	0.0055 (18)	−0.0031 (16)
C10	0.055 (2)	0.056 (2)	0.074 (2)	−0.0089 (18)	−0.0058 (19)	−0.0026 (19)
C11	0.064 (3)	0.046 (2)	0.081 (3)	−0.0148 (17)	−0.005 (2)	−0.0007 (19)
C12	0.063 (2)	0.048 (2)	0.071 (2)	−0.0078 (18)	−0.006 (2)	0.0029 (18)
C13	0.048 (2)	0.052 (2)	0.056 (2)	−0.0046 (16)	0.0005 (16)	−0.0087 (17)
C14	0.072 (3)	0.051 (2)	0.089 (3)	−0.0002 (19)	−0.001 (2)	0.009 (2)
C15	0.150 (5)	0.093 (4)	0.093 (4)	0.017 (3)	0.009 (3)	0.031 (3)
C16	0.142 (5)	0.100 (4)	0.176 (6)	0.063 (4)	0.047 (4)	0.039 (4)
C17	0.057 (2)	0.064 (2)	0.076 (3)	−0.0052 (19)	−0.009 (2)	−0.007 (2)
C18	0.055 (3)	0.115 (4)	0.095 (3)	0.002 (2)	0.008 (2)	−0.010 (3)
C19	0.079 (3)	0.209 (6)	0.066 (3)	0.015 (4)	−0.008 (2)	−0.001 (4)
C20	0.053 (2)	0.049 (2)	0.0435 (19)	−0.0018 (15)	−0.0020 (15)	0.0021 (15)
C21	0.0465 (19)	0.0418 (18)	0.0415 (18)	−0.0037 (14)	−0.0040 (15)	0.0008 (14)
C22	0.060 (2)	0.058 (2)	0.058 (2)	−0.0121 (17)	0.0119 (18)	−0.0073 (18)
C23	0.087 (3)	0.092 (3)	0.057 (2)	−0.015 (2)	0.021 (2)	−0.023 (2)
C24	0.086 (3)	0.072 (3)	0.061 (2)	−0.017 (2)	0.006 (2)	−0.026 (2)
C25	0.069 (3)	0.052 (2)	0.063 (2)	−0.0127 (18)	−0.007 (2)	−0.0057 (18)
C26	0.060 (2)	0.0476 (19)	0.053 (2)	−0.0115 (16)	0.0066 (17)	−0.0043 (16)
C27	0.051 (2)	0.0449 (19)	0.050 (2)	−0.0129 (16)	0.0118 (16)	−0.0045 (15)
C28	0.051 (2)	0.048 (2)	0.059 (2)	−0.0067 (16)	0.0111 (17)	0.0016 (17)
C29	0.070 (3)	0.051 (2)	0.084 (3)	0.0049 (19)	0.020 (2)	−0.003 (2)
C30	0.092 (3)	0.063 (3)	0.072 (3)	−0.011 (2)	0.018 (3)	−0.022 (2)
C31	0.082 (3)	0.069 (3)	0.059 (2)	−0.017 (2)	−0.002 (2)	−0.011 (2)
C32	0.053 (2)	0.054 (2)	0.063 (2)	−0.0114 (17)	0.0042 (18)	−0.0030 (18)
C33	0.063 (3)	0.069 (3)	0.079 (3)	−0.005 (2)	−0.001 (2)	0.016 (2)
C34	0.066 (3)	0.295 (9)	0.120 (5)	0.017 (5)	0.007 (3)	0.050 (5)
C35	0.102 (4)	0.149 (5)	0.086 (3)	−0.016 (3)	−0.003 (3)	0.039 (3)
C36	0.066 (3)	0.061 (2)	0.098 (3)	−0.007 (2)	−0.008 (2)	−0.001 (2)
C37	0.075 (3)	0.113 (4)	0.161 (5)	0.018 (3)	0.023 (3)	0.019 (4)
C38	0.132 (5)	0.108 (4)	0.139 (5)	0.007 (3)	−0.019 (4)	0.052 (4)
N1	0.070 (2)	0.0464 (17)	0.0551 (19)	−0.0163 (15)	0.0106 (16)	−0.0071 (15)
N2	0.067 (2)	0.0471 (17)	0.0500 (19)	−0.0166 (14)	0.0114 (15)	−0.0080 (14)

Geometric parameters (Å, º) top

Br1—C1	1.901 (4)	C20—C25	1.371 (5)
Br2—C20	1.898 (4)	C20—C21	1.393 (4)
C1—C2	1.387 (5)	C21—C22	1.380 (4)
C1—C6	1.393 (5)	C21—C26	1.500 (4)
C2—C3	1.386 (4)	C22—C23	1.381 (5)
C2—C7	1.501 (4)	C22—H22	0.9300
C3—C4	1.376 (5)	C23—C24	1.358 (6)
C3—H3	0.9300	C23—H23	0.9300
C4—C5	1.372 (6)	C24—C25	1.359 (5)
C4—H4	0.9300	C24—H24	0.9300
C5—C6	1.362 (6)	C25—H25	0.9300
C5—H5	0.9300	C26—N2	1.454 (4)
C6—H6	0.9300	C26—H26A	0.9700
C7—N1	1.462 (4)	C26—H26B	0.9700
C7—H7A	0.9700	C27—C28	1.392 (5)
C7—H7B	0.9700	C27—C32	1.398 (5)
C8—C13	1.387 (5)	C27—N2	1.430 (4)
C8—C9	1.396 (5)	C28—C29	1.378 (5)
C8—N1	1.438 (4)	C28—C33	1.518 (5)
C9—C10	1.374 (5)	C29—C30	1.361 (6)
C9—C14	1.518 (5)	C29—H29	0.9300
C10—C11	1.364 (5)	C30—C31	1.355 (6)
C10—H10	0.9300	C30—H30	0.9300
C11—C12	1.375 (5)	C31—C32	1.386 (5)
C11—H11	0.9300	C31—H31	0.9300
C12—C13	1.378 (5)	C32—C36	1.512 (5)
C12—H12	0.9300	C33—C34	1.487 (6)
C13—C17	1.519 (5)	C33—C35	1.502 (6)
C14—C16	1.502 (6)	C33—H33	0.9800
C14—C15	1.514 (6)	C34—H34A	0.9600
C14—H14	0.9800	C34—H34B	0.9600
C15—H15A	0.9600	C34—H34C	0.9600
C15—H15B	0.9600	C35—H35A	0.9600
C15—H15C	0.9600	C35—H35B	0.9600
C16—H16A	0.9600	C35—H35C	0.9600
C16—H16B	0.9600	C36—C37	1.511 (6)
C16—H16C	0.9600	C36—C38	1.527 (6)
C17—C18	1.505 (5)	C36—H36	0.9800
C17—C19	1.526 (6)	C37—H37A	0.9600
C17—H17	0.9800	C37—H37B	0.9600
C18—H18A	0.9600	C37—H37C	0.9600
C18—H18B	0.9600	C38—H38A	0.9600
C18—H18C	0.9600	C38—H38B	0.9600
C19—H19A	0.9600	C38—H38C	0.9600
C19—H19B	0.9600	N1—H1	0.863 (18)
C19—H19C	0.9600	N2—H2	0.814 (19)

C2—C1—C6	121.5 (3)	C22—C21—C20	116.7 (3)
C2—C1—Br1	120.4 (3)	C22—C21—C26	122.5 (3)
C6—C1—Br1	118.1 (3)	C20—C21—C26	120.8 (3)
C3—C2—C1	116.9 (3)	C21—C22—C23	121.4 (3)
C3—C2—C7	122.7 (3)	C21—C22—H22	119.3
C1—C2—C7	120.5 (3)	C23—C22—H22	119.3
C4—C3—C2	122.0 (3)	C24—C23—C22	119.8 (4)
C4—C3—H3	119.0	C24—C23—H23	120.1
C2—C3—H3	119.0	C22—C23—H23	120.1
C5—C4—C3	119.7 (4)	C23—C24—C25	120.7 (4)
C5—C4—H4	120.2	C23—C24—H24	119.6
C3—C4—H4	120.2	C25—C24—H24	119.6
C6—C5—C4	120.3 (4)	C24—C25—C20	119.5 (3)
C6—C5—H5	119.8	C24—C25—H25	120.3
C4—C5—H5	119.8	C20—C25—H25	120.3
C5—C6—C1	119.7 (4)	N2—C26—C21	112.2 (3)
C5—C6—H6	120.2	N2—C26—H26A	109.2
C1—C6—H6	120.2	C21—C26—H26A	109.2
N1—C7—C2	112.4 (3)	N2—C26—H26B	109.2
N1—C7—H7A	109.1	C21—C26—H26B	109.2
C2—C7—H7A	109.1	H26A—C26—H26B	107.9
N1—C7—H7B	109.1	C28—C27—C32	121.0 (3)
C2—C7—H7B	109.1	C28—C27—N2	120.2 (3)
H7A—C7—H7B	107.9	C32—C27—N2	118.7 (3)
C13—C8—C9	120.5 (3)	C29—C28—C27	118.1 (3)
C13—C8—N1	119.0 (3)	C29—C28—C33	120.4 (3)
C9—C8—N1	120.5 (3)	C27—C28—C33	121.4 (3)
C10—C9—C8	118.7 (3)	C30—C29—C28	121.1 (4)
C10—C9—C14	118.5 (3)	C30—C29—H29	119.4
C8—C9—C14	122.8 (3)	C28—C29—H29	119.4
C11—C10—C9	121.3 (3)	C31—C30—C29	120.8 (4)
C11—C10—H10	119.4	C31—C30—H30	119.6
C9—C10—H10	119.4	C29—C30—H30	119.6
C10—C11—C12	119.9 (3)	C30—C31—C32	120.8 (4)
C10—C11—H11	120.0	C30—C31—H31	119.6
C12—C11—H11	120.0	C32—C31—H31	119.6
C11—C12—C13	120.6 (3)	C31—C32—C27	118.0 (3)
C11—C12—H12	119.7	C31—C32—C36	120.1 (3)
C13—C12—H12	119.7	C27—C32—C36	121.9 (3)
C12—C13—C8	119.0 (3)	C34—C33—C35	109.9 (4)
C12—C13—C17	118.9 (3)	C34—C33—C28	113.7 (4)
C8—C13—C17	122.0 (3)	C35—C33—C28	112.0 (3)
C16—C14—C15	110.5 (4)	C34—C33—H33	107.0
C16—C14—C9	111.5 (4)	C35—C33—H33	107.0
C15—C14—C9	111.9 (3)	C28—C33—H33	107.0
C16—C14—H14	107.6	C33—C34—H34A	109.5
C15—C14—H14	107.6	C33—C34—H34B	109.5
C9—C14—H14	107.6	H34A—C34—H34B	109.5
C14—C15—H15A	109.5	C33—C34—H34C	109.5
C14—C15—H15B	109.5	H34A—C34—H34C	109.5
H15A—C15—H15B	109.5	H34B—C34—H34C	109.5
C14—C15—H15C	109.5	C33—C35—H35A	109.5
H15A—C15—H15C	109.5	C33—C35—H35B	109.5
H15B—C15—H15C	109.5	H35A—C35—H35B	109.5
C14—C16—H16A	109.5	C33—C35—H35C	109.5
C14—C16—H16B	109.5	H35A—C35—H35C	109.5
H16A—C16—H16B	109.5	H35B—C35—H35C	109.5
C14—C16—H16C	109.5	C37—C36—C32	110.9 (4)
H16A—C16—H16C	109.5	C37—C36—C38	110.5 (4)
H16B—C16—H16C	109.5	C32—C36—C38	112.9 (4)
C18—C17—C13	111.4 (3)	C37—C36—H36	107.4
C18—C17—C19	109.8 (4)	C32—C36—H36	107.4
C13—C17—C19	111.9 (3)	C38—C36—H36	107.4
C18—C17—H17	107.8	C36—C37—H37A	109.5
C13—C17—H17	107.8	C36—C37—H37B	109.5
C19—C17—H17	107.8	H37A—C37—H37B	109.5
C17—C18—H18A	109.5	C36—C37—H37C	109.5
C17—C18—H18B	109.5	H37A—C37—H37C	109.5
H18A—C18—H18B	109.5	H37B—C37—H37C	109.5
C17—C18—H18C	109.5	C36—C38—H38A	109.5
H18A—C18—H18C	109.5	C36—C38—H38B	109.5
H18B—C18—H18C	109.5	H38A—C38—H38B	109.5
C17—C19—H19A	109.5	C36—C38—H38C	109.5
C17—C19—H19B	109.5	H38A—C38—H38C	109.5
H19A—C19—H19B	109.5	H38B—C38—H38C	109.5
C17—C19—H19C	109.5	C8—N1—C7	113.7 (3)
H19A—C19—H19C	109.5	C8—N1—H1	112 (3)
H19B—C19—H19C	109.5	C7—N1—H1	106 (3)
C25—C20—C21	121.9 (3)	C27—N2—C26	114.1 (3)
C25—C20—Br2	117.9 (3)	C27—N2—H2	122 (3)
C21—C20—Br2	120.2 (2)	C26—N2—H2	106 (3)

C6—C1—C2—C3	−0.2 (5)	Br2—C20—C21—C26	0.3 (4)
Br1—C1—C2—C3	−177.8 (2)	C20—C21—C22—C23	0.0 (5)
C6—C1—C2—C7	179.5 (3)	C26—C21—C22—C23	−179.7 (4)
Br1—C1—C2—C7	1.8 (4)	C21—C22—C23—C24	0.1 (6)
C1—C2—C3—C4	0.5 (5)	C22—C23—C24—C25	−0.1 (7)
C7—C2—C3—C4	−179.1 (3)	C23—C24—C25—C20	0.0 (6)
C2—C3—C4—C5	−1.0 (5)	C21—C20—C25—C24	0.0 (5)
C3—C4—C5—C6	1.1 (6)	Br2—C20—C25—C24	179.4 (3)
C4—C5—C6—C1	−0.8 (6)	C22—C21—C26—N2	0.5 (5)
C2—C1—C6—C5	0.3 (6)	C20—C21—C26—N2	−179.1 (3)
Br1—C1—C6—C5	178.0 (3)	C32—C27—C28—C29	1.9 (5)
C3—C2—C7—N1	9.6 (5)	N2—C27—C28—C29	−176.5 (3)
C1—C2—C7—N1	−170.1 (3)	C32—C27—C28—C33	179.6 (3)
C13—C8—C9—C10	−2.0 (5)	N2—C27—C28—C33	1.2 (5)
N1—C8—C9—C10	176.6 (3)	C27—C28—C29—C30	−0.7 (5)
C13—C8—C9—C14	179.0 (3)	C33—C28—C29—C30	−178.4 (3)
N1—C8—C9—C14	−2.4 (5)	C28—C29—C30—C31	−0.8 (6)
C8—C9—C10—C11	1.7 (5)	C29—C30—C31—C32	1.1 (6)
C14—C9—C10—C11	−179.3 (4)	C30—C31—C32—C27	0.1 (6)
C9—C10—C11—C12	−0.2 (6)	C30—C31—C32—C36	178.4 (4)
C10—C11—C12—C13	−1.0 (6)	C28—C27—C32—C31	−1.6 (5)
C11—C12—C13—C8	0.7 (5)	N2—C27—C32—C31	176.8 (3)
C11—C12—C13—C17	−176.0 (3)	C28—C27—C32—C36	−179.9 (3)
C9—C8—C13—C12	0.9 (5)	N2—C27—C32—C36	−1.5 (5)
N1—C8—C13—C12	−177.7 (3)	C29—C28—C33—C34	−43.1 (5)
C9—C8—C13—C17	177.4 (3)	C27—C28—C33—C34	139.3 (5)
N1—C8—C13—C17	−1.2 (5)	C29—C28—C33—C35	82.3 (5)
C10—C9—C14—C16	60.7 (5)	C27—C28—C33—C35	−95.4 (4)
C8—C9—C14—C16	−120.3 (5)	C31—C32—C36—C37	−85.3 (5)
C10—C9—C14—C15	−63.6 (5)	C27—C32—C36—C37	93.0 (5)
C8—C9—C14—C15	115.4 (4)	C31—C32—C36—C38	39.4 (5)
C12—C13—C17—C18	73.0 (5)	C27—C32—C36—C38	−142.4 (4)
C8—C13—C17—C18	−103.5 (4)	C13—C8—N1—C7	−85.2 (4)
C12—C13—C17—C19	−50.4 (5)	C9—C8—N1—C7	96.2 (4)
C8—C13—C17—C19	133.1 (4)	C2—C7—N1—C8	173.0 (3)
C25—C20—C21—C22	0.0 (5)	C28—C27—N2—C26	−90.3 (4)
Br2—C20—C21—C22	−179.4 (2)	C32—C27—N2—C26	91.2 (4)
C25—C20—C21—C26	179.6 (3)	C21—C26—N2—C27	175.8 (3)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C18—H18C···Br2	0.96	3.06	3.928 (5)	151

Experimental details

Crystal data
Chemical formula	C₁₉H₂₄BrN
M_r	346.30
Crystal system, space group	Monoclinic, P2₁/c
Temperature (K)	297
a, b, c (Å)	17.207 (17), 14.742 (15), 13.870 (14)
β (°)	94.650 (18)
V (Å³)	3507 (6)
Z	8
Radiation type	Mo Kα
µ (mm⁻¹)	2.34
Crystal size (mm)	0.60 × 0.33 × 0.31

Data collection
Diffractometer	Bruker SMART APEX CCD area-detector diffractometer
Absorption correction	Multi-scan (SADABS; Bruker 2001)
T_min, T_max	0.304, 0.483
No. of measured, independent and observed [I > 2σ(I)] reflections	27700, 7183, 4220
R_int	0.058
(sin θ/λ)_max (Å⁻¹)	0.625

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.047, 0.134, 1.03
No. of reflections	7183
No. of parameters	395
No. of restraints	2
H-atom treatment	H atoms treated by a mixture of independent and constrained refinement
Δρ_max, Δρ_min (e Å⁻³)	0.36, −0.33

Computer programs: SMART (Bruker, 2000), SAINT-Plus (Bruker, 2000), SHELXS97 (Sheldrick, 1997), SHELXTL (Bruker, 2001), DIAMOND (Brandenburg, 2006), publCIF (Westrip, 2007).