N-(4-Bromo­benzo­yl)-N,N′-dicyclo­hexyl­urea

Wang, Y.-W.; Peng, Y.

doi:10.1107/S1600536807064756

organic compounds

CRYSTALLOGRAPHIC
COMMUNICATIONS

ISSN: 2056-9890

Volume 64| Part 1| January 2008| Page o160

https://doi.org/10.1107/S1600536807064756

Open

access

N-(4-Bromobenzoyl)-N,N′-dicyclohexylurea

Ya-Wen Wang ^a and Yu Peng ^a ^*

^aState Key Laboratory of Applied Organic Chemistry, College of Chemistry and Chemical Engineering, Lanzhou University, Lanzhou 730000, People's Republic of China
^*Correspondence e-mail: pengyu@lzu.edu.cn

(Received 14 November 2007; accepted 30 November 2007; online 6 December 2007)

In the title compound, C₂₀H₂₇BrN₂O₂, molecules are linked into one-dimensional chains through (amide)N—H⋯O=C(amide) intermolecular hydrogen bonds.

Related literature

For related literature, see: Bohne et al. (2005 ); Bondy et al. (2004 ); Bruker (2000 ); Ślebioda (1995 ). For literature on related crystal structures, see: Ball et al. (1990 ); Chérioux et al. (2002 ); Gallagher et al. (1999 ); Govindasamy & Subramanian (1997 ); Toniolo et al. (1990 ); Wu et al. (2006 ).

Experimental

Crystal data

C₂₀H₂₇BrN₂O₂
M_r = 407.35
Monoclinic, P 2₁ /n
a = 13.501 (2) Å
b = 9.5621 (10) Å
c = 16.306 (2) Å
β = 114.443 (6)°
V = 1916.3 (4) Å³
Z = 4
Mo Kα radiation
μ = 2.16 mm⁻¹
T = 113 (2) K
0.38 × 0.16 × 0.14 mm

Data collection

Rigaku Saturn CCD diffractometer
Absorption correction: multi-scan (REQABS; Jacobson, 1998 ) T_min = 0.484, T_max = 0.739
17461 measured reflections
4526 independent reflections
3651 reflections with I > 2σ(I)
R_int = 0.044

Refinement

R[F² > 2σ(F²)] = 0.036
wR(F²) = 0.078
S = 1.06
4526 reflections
231 parameters
1 restraint
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.45 e Å⁻³
Δρ_min = −0.44 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N2—H2A⋯O2ⁱ	0.898 (10)	2.072 (11)	2.961 (2)	170 (2)
Symmetry code: (i) $[-x+{\script{3\over 2}}, y+{\script{1\over 2}}, -z+{\script{3\over 2}}]$ .

Data collection: CrystalClear (Jacobson, 1999 ); cell refinement: CrystalClear; data reduction: CrystalClear; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997 ); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEP-3 (Farrugia, 1997 ); software used to prepare material for publication: CrystalStructure (Rigaku, 1999 ).

Supporting information

Crystal structure: contains datablocks global, I. DOI: https://doi.org/10.1107/S1600536807064756/pk2071sup1.cif

Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S1600536807064756/pk2071Isup2.hkl

checkCIF report

Comment top

The first conscious total synthesis of a natural product was that of urea in 1828 by Wohler, which marks the beginnings of organic synthesis. Since then, many urea derivatives have been prepared and have demonstrated a wide range of uses, including fluorescence probes (Bohne et al., 2005) and anion receptors (Bondy et al., 2004).

The title compound, an N-acylurea derivative, can be conveniently prepared from dicyclohexylcarbodiimide (DCC) and p-bromobenzoic acid according to reported methods (Ślebioda, 1995). The molecular structure is shown in Fig.1. Each cyclohexyl group adopts the chair conformation, as is required for energy minimization. The two carbonyl groups are twisted substantially at the central atom, N1, with a dihedral angle of 66.43 (10)° between the O1/C7/N1 and O2/C14/N2 planes, which increases the distance between atoms O1 and N2. As a result, no intramolecular N2–H2A···O1 hydrogen bond is formed. However, molecules are linked into chains through (amide) N–H···O=C (amide) intermolecular hydrogen bonds, reinforced by C–H···O=C interactions. Surprisingly, this supramolecular arrangement is not observed in a closely related X-ray structure (Gallagher et al., 1999).

Related literature top

For related literature, see: Bohne et al. (2005); Bondy et al. (2004); Ślebioda (1995). For literature on related X-ray structures, see: Ball et al. (1990); Chérioux et al. (2002); Gallagher et al. (1999); Govindasamy & Subramanian (1997); Toniolo et al. (1990); Wu et al. (2006); Bruker (2000).

Experimental top

p-bromobenzoic acid (201 mg, 1 mmol) was dissolved in CHCl₃ (5 ml) and DCC (206 mg, 1 mmol) and N,N-dimethylpyridin-4-amine (122 mg, 1 mmol) were added to the solution. The resulting mixture was stirred for 1 h at 298 K. After evaporation of the solvent, a colorless solid was isolated. Single crystals suitable for X-ray structure determination were obtained by slow evaporation of a EtOAc solution over a period of several days.

Structure description top

Computing details top

Data collection: CrystalClear (Jacobson, 1999); cell refinement: CrystalClear; data reduction: CrystalClear; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEP-3 (Farrugia, 1997); software used to prepare material for publication: CrystalStructure (Rigaku, 1999).

Figures top

Fig. 1. An ellipsoid plot of the title compound, showing the atom-labelling scheme. Displacement ellipsoids are drawn at the 50% probability level.

N-(4-Bromobenzoyl)-N,N'-dicyclohexylurea top

Crystal data top

C₂₀H₂₇BrN₂O₂	F(000) = 848
M_r = 407.35	D_x = 1.412 Mg m⁻³
Monoclinic, P2₁/n	Mo Kα radiation, λ = 0.71070 Å
Hall symbol: -P 2yn	Cell parameters from 4164 reflections
a = 13.501 (2) Å	θ = 1.7–27.9°
b = 9.5621 (10) Å	µ = 2.16 mm⁻¹
c = 16.306 (2) Å	T = 113 K
β = 114.443 (6)°	Prism, colorless
V = 1916.3 (4) Å³	0.38 × 0.16 × 0.14 mm
Z = 4

Data collection top

Rigaku Saturn CCD diffractometer	4526 independent reflections
Radiation source: Rotating anode	3651 reflections with I > 2σ(I)
Confocal monochromator	R_int = 0.044
Detector resolution: 7.31 pixels mm^-1	θ_max = 27.9°, θ_min = 1.7°
ω scans	h = −17→17
Absorption correction: multi-scan (REQABS; Jacobson, 1998)	k = −12→12
T_min = 0.484, T_max = 0.739	l = −21→20
17461 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)] = 0.036	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.078	H atoms treated by a mixture of independent and constrained refinement
S = 1.06	w = 1/[σ²(F_o²) + (0.0381P)²] where P = (F_o² + 2F_c²)/3
4526 reflections	(Δ/σ)_max = 0.003
231 parameters	Δρ_max = 0.45 e Å⁻³
1 restraint	Δρ_min = −0.44 e Å⁻³

Crystal data top

C₂₀H₂₇BrN₂O₂	V = 1916.3 (4) Å³
M_r = 407.35	Z = 4
Monoclinic, P2₁/n	Mo Kα radiation
a = 13.501 (2) Å	µ = 2.16 mm⁻¹
b = 9.5621 (10) Å	T = 113 K
c = 16.306 (2) Å	0.38 × 0.16 × 0.14 mm
β = 114.443 (6)°

Data collection top

Rigaku Saturn CCD diffractometer	4526 independent reflections
Absorption correction: multi-scan (REQABS; Jacobson, 1998)	3651 reflections with I > 2σ(I)
T_min = 0.484, T_max = 0.739	R_int = 0.044
17461 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.036	1 restraint
wR(F²) = 0.078	H atoms treated by a mixture of independent and constrained refinement
S = 1.06	Δρ_max = 0.45 e Å⁻³
4526 reflections	Δρ_min = −0.44 e Å⁻³
231 parameters

Special details top

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 > 2σ(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	0.615319 (17)	0.39160 (2)	1.092233 (14)	0.03591 (9)
N1	0.86443 (11)	0.53780 (15)	0.80694 (9)	0.0172 (3)
N2	0.67615 (11)	0.53992 (16)	0.73657 (10)	0.0180 (3)
O1	0.95485 (9)	0.68643 (13)	0.92419 (8)	0.0226 (3)
O2	0.76754 (10)	0.34042 (13)	0.73292 (8)	0.0234 (3)
C1	0.69576 (14)	0.4583 (2)	1.02792 (12)	0.0233 (4)
C2	0.69278 (15)	0.5987 (2)	1.00682 (13)	0.0267 (4)
H2	0.6508	0.6624	1.0240	0.032*
C3	0.75215 (15)	0.6450 (2)	0.96011 (13)	0.0246 (4)
H3	0.7519	0.7414	0.9460	0.029*
C4	0.81235 (13)	0.55047 (19)	0.93373 (11)	0.0176 (4)
C5	0.81418 (14)	0.40955 (19)	0.95585 (12)	0.0205 (4)
H5	0.8551	0.3450	0.9381	0.025*
C6	0.75616 (14)	0.3634 (2)	1.00396 (12)	0.0223 (4)
H6	0.7581	0.2677	1.0202	0.027*
C7	0.88221 (13)	0.60122 (18)	0.88777 (12)	0.0179 (4)
C8	0.94261 (14)	0.55666 (19)	0.76516 (12)	0.0199 (4)
H8	0.9907	0.6372	0.7963	0.024*
C9	1.01578 (15)	0.4287 (2)	0.77921 (14)	0.0259 (4)
H9A	0.9702	0.3452	0.7531	0.031*
H9B	1.0574	0.4122	0.8445	0.031*
C10	1.09504 (16)	0.4493 (2)	0.73482 (14)	0.0331 (5)
H10A	1.1462	0.5260	0.7656	0.040*
H10B	1.1380	0.3628	0.7415	0.040*
C11	1.03445 (17)	0.4842 (2)	0.63510 (14)	0.0361 (5)
H11A	0.9878	0.4043	0.6032	0.043*
H11B	1.0874	0.5007	0.6086	0.043*
C12	0.96424 (17)	0.6143 (2)	0.62288 (14)	0.0341 (5)
H12A	0.9238	0.6338	0.5578	0.041*
H12B	1.0117	0.6956	0.6507	0.041*
C13	0.88348 (15)	0.5955 (2)	0.66570 (13)	0.0268 (4)
H13A	0.8424	0.6834	0.6599	0.032*
H13B	0.8308	0.5210	0.6335	0.032*
C14	0.76568 (14)	0.4618 (2)	0.75616 (11)	0.0180 (4)
C15	0.56540 (13)	0.48403 (19)	0.69141 (12)	0.0180 (4)
H15	0.5702	0.3853	0.6733	0.022*
C16	0.50196 (16)	0.5682 (2)	0.60708 (13)	0.0313 (5)
H16A	0.5392	0.5639	0.5661	0.038*
H16B	0.4987	0.6673	0.6233	0.038*
C17	0.38642 (16)	0.5099 (2)	0.55931 (15)	0.0399 (6)
H17A	0.3452	0.5668	0.5051	0.048*
H17B	0.3899	0.4128	0.5396	0.048*
C18	0.32755 (16)	0.5114 (2)	0.62076 (18)	0.0509 (7)
H18A	0.3189	0.6091	0.6368	0.061*
H18B	0.2542	0.4702	0.5890	0.061*
C19	0.39104 (16)	0.4288 (2)	0.70547 (16)	0.0403 (6)
H19A	0.3934	0.3293	0.6896	0.048*
H19B	0.3535	0.4344	0.7462	0.048*
C20	0.50804 (16)	0.4842 (2)	0.75473 (14)	0.0296 (5)
H20A	0.5063	0.5805	0.7764	0.036*
H20B	0.5487	0.4245	0.8077	0.036*
H2A	0.6851 (15)	0.6326 (10)	0.7456 (12)	0.023 (5)*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Br1	0.03720 (13)	0.04748 (17)	0.03229 (13)	−0.01255 (10)	0.02362 (10)	−0.00410 (10)
N1	0.0147 (7)	0.0164 (8)	0.0206 (8)	−0.0024 (6)	0.0075 (6)	−0.0004 (6)
N2	0.0154 (7)	0.0136 (9)	0.0238 (8)	−0.0013 (6)	0.0070 (6)	−0.0024 (7)
O1	0.0190 (6)	0.0223 (7)	0.0233 (7)	−0.0054 (6)	0.0056 (5)	−0.0015 (6)
O2	0.0213 (6)	0.0140 (7)	0.0322 (8)	0.0006 (5)	0.0084 (6)	−0.0032 (6)
C1	0.0217 (9)	0.0320 (12)	0.0174 (9)	−0.0071 (8)	0.0093 (8)	−0.0027 (9)
C2	0.0257 (10)	0.0269 (12)	0.0320 (11)	−0.0048 (8)	0.0165 (9)	−0.0102 (9)
C3	0.0259 (10)	0.0198 (11)	0.0297 (10)	−0.0034 (8)	0.0132 (8)	−0.0030 (9)
C4	0.0141 (8)	0.0212 (10)	0.0151 (8)	−0.0030 (7)	0.0037 (7)	−0.0019 (8)
C5	0.0164 (8)	0.0239 (11)	0.0194 (9)	0.0003 (8)	0.0057 (7)	0.0005 (8)
C6	0.0218 (9)	0.0244 (11)	0.0191 (9)	−0.0012 (8)	0.0067 (8)	0.0040 (8)
C7	0.0145 (8)	0.0166 (10)	0.0198 (9)	0.0026 (7)	0.0045 (7)	0.0037 (8)
C8	0.0171 (9)	0.0203 (10)	0.0252 (10)	−0.0019 (7)	0.0117 (8)	−0.0001 (8)
C9	0.0188 (9)	0.0267 (11)	0.0306 (11)	0.0044 (8)	0.0087 (8)	0.0030 (9)
C10	0.0221 (10)	0.0396 (13)	0.0405 (12)	0.0087 (9)	0.0159 (9)	0.0002 (11)
C11	0.0321 (11)	0.0479 (14)	0.0351 (12)	0.0045 (10)	0.0209 (10)	−0.0050 (11)
C12	0.0348 (11)	0.0463 (14)	0.0290 (11)	0.0046 (10)	0.0210 (10)	0.0048 (10)
C13	0.0245 (10)	0.0332 (12)	0.0264 (10)	0.0058 (9)	0.0144 (8)	0.0065 (9)
C14	0.0176 (9)	0.0184 (10)	0.0179 (9)	−0.0019 (7)	0.0074 (7)	0.0019 (8)
C15	0.0141 (8)	0.0162 (10)	0.0219 (9)	−0.0008 (7)	0.0055 (7)	−0.0019 (8)
C16	0.0314 (11)	0.0229 (11)	0.0270 (11)	−0.0040 (9)	−0.0006 (9)	0.0023 (9)
C17	0.0268 (11)	0.0284 (13)	0.0408 (13)	0.0028 (9)	−0.0096 (10)	0.0015 (10)
C18	0.0150 (10)	0.0391 (14)	0.0841 (19)	0.0034 (10)	0.0060 (12)	−0.0301 (14)
C19	0.0277 (11)	0.0528 (15)	0.0518 (15)	−0.0179 (10)	0.0279 (11)	−0.0276 (12)
C20	0.0262 (10)	0.0367 (13)	0.0304 (11)	−0.0088 (9)	0.0163 (9)	−0.0101 (10)

Geometric parameters (Å, º) top

Br1—C1	1.9048 (18)	C10—H10A	0.9900
N1—C7	1.379 (2)	C10—H10B	0.9900
N1—C14	1.441 (2)	C11—C12	1.526 (3)
N1—C8	1.485 (2)	C11—H11A	0.9900
N2—C14	1.342 (2)	C11—H11B	0.9900
N2—C15	1.467 (2)	C12—C13	1.529 (2)
N2—H2A	0.898 (9)	C12—H12A	0.9900
O1—C7	1.223 (2)	C12—H12B	0.9900
O2—C14	1.225 (2)	C13—H13A	0.9900
C1—C6	1.380 (3)	C13—H13B	0.9900
C1—C2	1.382 (3)	C15—C16	1.516 (2)
C2—C3	1.387 (3)	C15—C20	1.526 (2)
C2—H2	0.9500	C15—H15	1.0000
C3—C4	1.397 (3)	C16—C17	1.531 (3)
C3—H3	0.9500	C16—H16A	0.9900
C4—C5	1.393 (3)	C16—H16B	0.9900
C4—C7	1.507 (2)	C17—C18	1.515 (3)
C5—C6	1.390 (2)	C17—H17A	0.9900
C5—H5	0.9500	C17—H17B	0.9900
C6—H6	0.9500	C18—C19	1.512 (3)
C8—C13	1.528 (2)	C18—H18A	0.9900
C8—C9	1.529 (3)	C18—H18B	0.9900
C8—H8	1.0000	C19—C20	1.540 (3)
C9—C10	1.532 (3)	C19—H19A	0.9900
C9—H9A	0.9900	C19—H19B	0.9900
C9—H9B	0.9900	C20—H20A	0.9900
C10—C11	1.524 (3)	C20—H20B	0.9900

C7—N1—C14	121.65 (14)	C11—C12—C13	111.49 (17)
C7—N1—C8	120.63 (14)	C11—C12—H12A	109.3
C14—N1—C8	117.50 (14)	C13—C12—H12A	109.3
C14—N2—C15	123.18 (15)	C11—C12—H12B	109.3
C14—N2—H2A	117.5 (12)	C13—C12—H12B	109.3
C15—N2—H2A	118.8 (12)	H12A—C12—H12B	108.0
C6—C1—C2	121.85 (17)	C8—C13—C12	110.81 (16)
C6—C1—Br1	118.30 (15)	C8—C13—H13A	109.5
C2—C1—Br1	119.85 (14)	C12—C13—H13A	109.5
C1—C2—C3	118.86 (18)	C8—C13—H13B	109.5
C1—C2—H2	120.6	C12—C13—H13B	109.5
C3—C2—H2	120.6	H13A—C13—H13B	108.1
C2—C3—C4	120.33 (18)	O2—C14—N2	125.83 (16)
C2—C3—H3	119.8	O2—C14—N1	121.54 (16)
C4—C3—H3	119.8	N2—C14—N1	112.60 (16)
C5—C4—C3	119.75 (17)	N2—C15—C16	109.75 (14)
C5—C4—C7	119.52 (16)	N2—C15—C20	110.93 (14)
C3—C4—C7	120.56 (17)	C16—C15—C20	111.03 (16)
C6—C5—C4	119.98 (17)	N2—C15—H15	108.3
C6—C5—H5	120.0	C16—C15—H15	108.3
C4—C5—H5	120.0	C20—C15—H15	108.3
C1—C6—C5	119.22 (18)	C15—C16—C17	110.02 (16)
C1—C6—H6	120.4	C15—C16—H16A	109.7
C5—C6—H6	120.4	C17—C16—H16A	109.7
O1—C7—N1	122.99 (16)	C15—C16—H16B	109.7
O1—C7—C4	120.93 (16)	C17—C16—H16B	109.7
N1—C7—C4	115.88 (15)	H16A—C16—H16B	108.2
N1—C8—C13	110.98 (14)	C18—C17—C16	111.28 (18)
N1—C8—C9	111.83 (15)	C18—C17—H17A	109.4
C13—C8—C9	112.02 (16)	C16—C17—H17A	109.4
N1—C8—H8	107.2	C18—C17—H17B	109.4
C13—C8—H8	107.2	C16—C17—H17B	109.4
C9—C8—H8	107.2	H17A—C17—H17B	108.0
C8—C9—C10	111.13 (16)	C19—C18—C17	110.18 (17)
C8—C9—H9A	109.4	C19—C18—H18A	109.6
C10—C9—H9A	109.4	C17—C18—H18A	109.6
C8—C9—H9B	109.4	C19—C18—H18B	109.6
C10—C9—H9B	109.4	C17—C18—H18B	109.6
H9A—C9—H9B	108.0	H18A—C18—H18B	108.1
C11—C10—C9	111.13 (16)	C18—C19—C20	111.59 (18)
C11—C10—H10A	109.4	C18—C19—H19A	109.3
C9—C10—H10A	109.4	C20—C19—H19A	109.3
C11—C10—H10B	109.4	C18—C19—H19B	109.3
C9—C10—H10B	109.4	C20—C19—H19B	109.3
H10A—C10—H10B	108.0	H19A—C19—H19B	108.0
C10—C11—C12	110.37 (17)	C15—C20—C19	110.18 (16)
C10—C11—H11A	109.6	C15—C20—H20A	109.6
C12—C11—H11A	109.6	C19—C20—H20A	109.6
C10—C11—H11B	109.6	C15—C20—H20B	109.6
C12—C11—H11B	109.6	C19—C20—H20B	109.6
H11A—C11—H11B	108.1	H20A—C20—H20B	108.1

C6—C1—C2—C3	0.1 (3)	C13—C8—C9—C10	54.1 (2)
Br1—C1—C2—C3	179.88 (14)	C8—C9—C10—C11	−55.5 (2)
C1—C2—C3—C4	1.0 (3)	C9—C10—C11—C12	57.0 (2)
C2—C3—C4—C5	−1.1 (3)	C10—C11—C12—C13	−57.3 (2)
C2—C3—C4—C7	−176.41 (17)	N1—C8—C13—C12	−179.79 (15)
C3—C4—C5—C6	0.0 (3)	C9—C8—C13—C12	−54.0 (2)
C7—C4—C5—C6	175.39 (15)	C11—C12—C13—C8	55.7 (2)
C2—C1—C6—C5	−1.2 (3)	C15—N2—C14—O2	6.6 (3)
Br1—C1—C6—C5	179.06 (13)	C15—N2—C14—N1	−175.26 (14)
C4—C5—C6—C1	1.1 (3)	C7—N1—C14—O2	−125.42 (18)
C14—N1—C7—O1	−166.44 (16)	C8—N1—C14—O2	60.0 (2)
C8—N1—C7—O1	7.9 (2)	C7—N1—C14—N2	56.4 (2)
C14—N1—C7—C4	18.6 (2)	C8—N1—C14—N2	−118.19 (17)
C8—N1—C7—C4	−167.06 (14)	C14—N2—C15—C16	−124.11 (18)
C5—C4—C7—O1	−117.18 (19)	C14—N2—C15—C20	112.83 (19)
C3—C4—C7—O1	58.1 (2)	N2—C15—C16—C17	179.70 (16)
C5—C4—C7—N1	57.9 (2)	C20—C15—C16—C17	−57.3 (2)
C3—C4—C7—N1	−126.75 (18)	C15—C16—C17—C18	57.9 (2)
C7—N1—C8—C13	−131.60 (17)	C16—C17—C18—C19	−57.3 (2)
C14—N1—C8—C13	43.0 (2)	C17—C18—C19—C20	56.3 (2)
C7—N1—C8—C9	102.52 (19)	N2—C15—C20—C19	178.56 (17)
C14—N1—C8—C9	−82.87 (19)	C16—C15—C20—C19	56.2 (2)
N1—C8—C9—C10	179.38 (15)	C18—C19—C20—C15	−55.8 (2)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N2—H2A···O2ⁱ	0.90 (1)	2.07 (1)	2.961 (2)	170 (2)

Symmetry code: (i) −x+3/2, y+1/2, −z+3/2.

Experimental details

Crystal data
Chemical formula	C₂₀H₂₇BrN₂O₂
M_r	407.35
Crystal system, space group	Monoclinic, P2₁/n
Temperature (K)	113
a, b, c (Å)	13.501 (2), 9.5621 (10), 16.306 (2)
β (°)	114.443 (6)
V (Å³)	1916.3 (4)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	2.16
Crystal size (mm)	0.38 × 0.16 × 0.14

Data collection
Diffractometer	Rigaku Saturn CCD diffractometer
Absorption correction	Multi-scan (REQABS; Jacobson, 1998)
T_min, T_max	0.484, 0.739
No. of measured, independent and observed [I > 2σ(I)] reflections	17461, 4526, 3651
R_int	0.044
(sin θ/λ)_max (Å⁻¹)	0.658

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.036, 0.078, 1.06
No. of reflections	4526
No. of parameters	231
No. of restraints	1
H-atom treatment	H atoms treated by a mixture of independent and constrained refinement
Δρ_max, Δρ_min (e Å⁻³)	0.45, −0.44

Computer programs: CrystalClear (Jacobson, 1999), CrystalClear, SHELXS97 (Sheldrick, 1997), SHELXL97 (Sheldrick, 1997), ORTEP-3 (Farrugia, 1997), CrystalStructure (Rigaku, 1999).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N2—H2A···O2ⁱ	0.898 (10)	2.072 (11)	2.961 (2)	170 (2)

Symmetry code: (i) −x+3/2, y+1/2, −z+3/2.

Acknowledgements

The authors acknowledge financial support from the Research Fund for New Faculty at the State Key Laboratory of Applied Organic Chemistry.

References

Ball, R. G., Brown, R. S. & Bennet, A. J. (1990). Acta Cryst. C46, 2491–2493. CSD CrossRef CAS IUCr Journals Google Scholar
Bohne, C., Ihmels, H., Waidelich, M. & Yihwa, C. (2005). J. Am. Chem. Soc. 127, 17158–17159. Web of Science CrossRef PubMed CAS Google Scholar
Bondy, C. R., Gale, P. A. & Loeb, S. J. (2004). J. Am. Chem. Soc. 126, 5030–5031. Web of Science CSD CrossRef PubMed CAS Google Scholar
Bruker (2000). SHELXTL. Version 6.10. Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
Chérioux, F., Therrien, B., Stoeckli-Evans, H. & Süss-Fink, G. (2002). Acta Cryst. E58, o27–o29. Web of Science CSD CrossRef IUCr Journals Google Scholar
Farrugia, L. J. (1997). J. Appl. Cryst. 30, 565 CrossRef CAS IUCr Journals Google Scholar
Gallagher, J. F., Kenny, P. T. M. & Sheehy, M. J. (1999). Acta Cryst. C55, 1607–1610. CSD CrossRef CAS IUCr Journals Google Scholar
Govindasamy, L. & Subramanian, E. (1997). Acta Cryst. C53, 927–928. CSD CrossRef CAS Web of Science IUCr Journals Google Scholar
Jacobson, R. A. (1998). REQABS. Version 1.1. MSC, The Woodlands, Texas, USA. Google Scholar
Jacobson, R. A. (1999). CrystalClear. Rigaku Corporation, The Woodlands, Texas, USA. Google Scholar
Rigaku (1999). CrystalStructure. Version 3.7.0. Rigaku Corporation, Tokyo, Japan. Google Scholar
Sheldrick, G. M. (1997). SHELXS97 and SHELXL97. University of Göttingen, Germany. Google Scholar
Ślebioda, M. (1995). Tetrahedron, 51, 7829–7834. Google Scholar
Toniolo, C., Valle, G., Crisma, M., Moretto, V., Izdebski, J., Pelka, J. & Schneider, C. H. (1990). Helv. Chim. Acta, 73, 626–634. CSD CrossRef CAS Web of Science Google Scholar
Wu, L., Liu, H.-M., Zhao, W.-T. & Zhang, W.-Q. (2006). Acta Cryst. C62, o435–o437. Web of Science CSD CrossRef CAS IUCr Journals Google Scholar