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Acta Cryst. (2007). E63, o3635-o3636
https://doi.org/10.1107/S160053680703646X
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Diethyl 4-(4-bromo­phen­yl)-2,6-dimethyl-1,4-dihydro­pyridine-3,5-dicarboxyl­ate

R. Boulcina, S. Bouacida, T. Roisnel and A. Debache
In the title compound, C19H22BrNO4, the dihydro­pyridine ring adopts a flattened boat conformation and the plane of the base of the boat forms a dihedral angle of 89.32 (5)° with the benzene ring. The crystal structure can be described as layers in which dihydro­pyridine rings are parallel to the (\overline{1}01) plane. The packing is stabilized by intra­molecular C—H...O and inter­molecular N—H...O hydrogen bonds, resulting in the formation of a three-dimensional network.
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Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S160053680703646X/at2352sup1.cif
Contains datablocks global, I

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S160053680703646X/at2352Isup2.hkl
Contains datablock I

CCDC reference: 657868

checkCIF report

Key indicators

  • Single-crystal X-ray study
  • T = 295 K
  • Mean [sigma](C-C) = 0.003 Å
  • R factor = 0.027
  • wR factor = 0.093
  • Data-to-parameter ratio = 18.0

checkCIF/PLATON results

No syntax errors found




Alert level C
PLAT431_ALERT_2_C Short Inter HL..A Contact  Br     ..  O1      ..       3.30 Ang.


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

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

1,4-Dihydropyridines (1,4-DHPs) have recently received great attention because of their wide range of therapeutic and pharmacological activities, such as antiviral, antitumor, antibacterial, and anti-inflammatory behaviour. Furthermore, these compounds have emerged as the integral backbones of several calcium channel blockers (Litvic et al., 2005), and as drugs for the treatment of cardiovascular diseases and hypertension (Bossert et al., 1981; Nakayama et al., 1996; Mulder et al., 2006). The dihydropyridine skeleton is common in many vasodilator, bronchiodilator, anti-atherosclerotic, anti-tumor, hepatoprotective and anti-diabetic agents (Mannhold et al., 1992). They are also known as neuroprotectants, as anti-platelet treatment of aggregators and are important in Alzheimer's disease as anti-ischaemic agents (Klusa, 1995; Bretzel et al., 1993). Among the 1,4-dihydropyridines there are also drug-resistance modifiers (Sridhar et al., 2005), antioxidants (Heravi et al., 2005) and a drug for the treatment of urinary urge incontinence (Moseley et al., 2005). Interest in 1,4-dihydropyridines is also sustained by their structural closeness to nicotinamide dinucleotide, a cofactor used by many reductases in metabolism (Tewari et al., 2004). Although 1,4-dihydropyridines with various aromatic, heteroaromatic, aliphatic and sugar substituents at C-4 have been reported as anti-tuberculosis agents (Geirsson et al., 1996). The simplest and the most straightforward procedure, originally reported by Hantzsch, involves the three-component, one-pot condensation of an aldehyde, β-keto ester, and ammonia under strongly refluxing conditions (Hantzsch, 1882). Therefore, synthesis of the 1,4-dihydropyridine nucleus continuously received the attention of scientists. This has led to the recent disclosure of several improved reaction procedures for the synthesis of 1,4-dihydropyridines, by either modification of the classical one-pot Hantzsch approach itself, or the development of novel, but more complex multistep strategies (Breitenbucher et al., 2000; Tu et al., 2001; Dondoni et al., 2004; Bennasar et al., 2005; Gómez et al., 2005). As a part of our program aiming at developing selective and environmental friendly methodologies for the reparation of fine chemicals and in continuation of our interest in new catalysts for multi-component reactions (Debache et al., 2006), in this paper, we wish to highlight our finding about the four-component Hantzsch reaction in refluxing ethanol as a solvent. In this study, we have synthesized diethyl 4-(4-bromophenyl)-2,6-dimethyl-1,4-dihydropyridine-3,5-dicarboxylate, (I), and characterized by X-ray diffraction method.

The molecular geometry and the atom-numbering scheme of (I) are shown in Fig. 1. The asymmetric unit of title compound contains a dimethyldihydropyridine group linked to a bromophenyl moiety and two ethylcarboxylate.

The geometric parameters of (I) are in agreement with those of other structures possessing a dihydropyridine substituent previously reported in the literature (Doreswamy et al., 2004; Mahendra et al., 2004).

The dihydropyridine ring adopts a flat boat conformation when C4 and N1 atoms are significantly displaced from dihydropyridine ring by -0.144 and 0.106 Å respectively, and its mean plane forms dihedral angles of 89.32 (5)° with phenyl substituent.

The crystal structure can be described by layers which dihydropyridine ring is parallel to (101) plane (Fig. 2).

The packing of (I) is stabilized by classical intramolecular C—H···O and intermolecular N—H···O hydrogen bonds, resulting in the formation of two dimensional network (Fig. 2). Additional hydrogen-bonding parameters are listed in Table 1.

Related literature top

For synthesis, see: Dondoni et al. (2004); Bennasar et al. (2005). For geometry, see: Doreswamy et al. (2004); Mahendra et al. (2004). For applications, see: Mulder et al. (2006); Litvic et al. (2005); Moseley (2005). For related literature, see: Bossert et al. (1981); Breitenbucher & Figliozzi (2000); Bretzel et al. (1993); Debache et al. (2006); Geirsson & Johannesdottir (1996); Gómez et al. (2005); Hantzsch (1882); Heravi et al. (2005); Klusa (1995); Mannhold et al. (1992); Nakayama & Kasoka (1996); Sridhar & Perumal (2005); Tewari et al. (2004); Tu et al. (2001).

Experimental top

A mixture of 4-bromobenzaldehyde (5 mmol), ethyl acetoacetate (10 mmol) and ammonium acetate (10 mmol) was refluxed in ethanol (10 ml) for 5 h. The reaction mixture was poured in cold water and extracted with ethyl acetate. The organic layer was washed with brine, dried over Na2SO4 and concentrated to give an analytically pure compound. The crude product was purified by recrystallization from ethanol to afford 1,4-dihydropyridines in 90% yields.

Refinement top

All H atoms were localized on Fourier maps, but introduced in calculated positions and treated as riding on their parent C atom, with N—H = 082, C—H = 0.93–0.97 Å, and with Uiso(H) = 1.2Ueq(C, N) or 1.5Ueq(Cmethyl).

Structure description top

1,4-Dihydropyridines (1,4-DHPs) have recently received great attention because of their wide range of therapeutic and pharmacological activities, such as antiviral, antitumor, antibacterial, and anti-inflammatory behaviour. Furthermore, these compounds have emerged as the integral backbones of several calcium channel blockers (Litvic et al., 2005), and as drugs for the treatment of cardiovascular diseases and hypertension (Bossert et al., 1981; Nakayama et al., 1996; Mulder et al., 2006). The dihydropyridine skeleton is common in many vasodilator, bronchiodilator, anti-atherosclerotic, anti-tumor, hepatoprotective and anti-diabetic agents (Mannhold et al., 1992). They are also known as neuroprotectants, as anti-platelet treatment of aggregators and are important in Alzheimer's disease as anti-ischaemic agents (Klusa, 1995; Bretzel et al., 1993). Among the 1,4-dihydropyridines there are also drug-resistance modifiers (Sridhar et al., 2005), antioxidants (Heravi et al., 2005) and a drug for the treatment of urinary urge incontinence (Moseley et al., 2005). Interest in 1,4-dihydropyridines is also sustained by their structural closeness to nicotinamide dinucleotide, a cofactor used by many reductases in metabolism (Tewari et al., 2004). Although 1,4-dihydropyridines with various aromatic, heteroaromatic, aliphatic and sugar substituents at C-4 have been reported as anti-tuberculosis agents (Geirsson et al., 1996). The simplest and the most straightforward procedure, originally reported by Hantzsch, involves the three-component, one-pot condensation of an aldehyde, β-keto ester, and ammonia under strongly refluxing conditions (Hantzsch, 1882). Therefore, synthesis of the 1,4-dihydropyridine nucleus continuously received the attention of scientists. This has led to the recent disclosure of several improved reaction procedures for the synthesis of 1,4-dihydropyridines, by either modification of the classical one-pot Hantzsch approach itself, or the development of novel, but more complex multistep strategies (Breitenbucher et al., 2000; Tu et al., 2001; Dondoni et al., 2004; Bennasar et al., 2005; Gómez et al., 2005). As a part of our program aiming at developing selective and environmental friendly methodologies for the reparation of fine chemicals and in continuation of our interest in new catalysts for multi-component reactions (Debache et al., 2006), in this paper, we wish to highlight our finding about the four-component Hantzsch reaction in refluxing ethanol as a solvent. In this study, we have synthesized diethyl 4-(4-bromophenyl)-2,6-dimethyl-1,4-dihydropyridine-3,5-dicarboxylate, (I), and characterized by X-ray diffraction method.

The molecular geometry and the atom-numbering scheme of (I) are shown in Fig. 1. The asymmetric unit of title compound contains a dimethyldihydropyridine group linked to a bromophenyl moiety and two ethylcarboxylate.

The geometric parameters of (I) are in agreement with those of other structures possessing a dihydropyridine substituent previously reported in the literature (Doreswamy et al., 2004; Mahendra et al., 2004).

The dihydropyridine ring adopts a flat boat conformation when C4 and N1 atoms are significantly displaced from dihydropyridine ring by -0.144 and 0.106 Å respectively, and its mean plane forms dihedral angles of 89.32 (5)° with phenyl substituent.

The crystal structure can be described by layers which dihydropyridine ring is parallel to (101) plane (Fig. 2).

The packing of (I) is stabilized by classical intramolecular C—H···O and intermolecular N—H···O hydrogen bonds, resulting in the formation of two dimensional network (Fig. 2). Additional hydrogen-bonding parameters are listed in Table 1.

For synthesis, see: Dondoni et al. (2004); Bennasar et al. (2005). For geometry, see: Doreswamy et al. (2004); Mahendra et al. (2004). For applications, see: Mulder et al. (2006); Litvic et al. (2005); Moseley (2005). For related literature, see: Bossert et al. (1981); Breitenbucher & Figliozzi (2000); Bretzel et al. (1993); Debache et al. (2006); Geirsson & Johannesdottir (1996); Gómez et al. (2005); Hantzsch (1882); Heravi et al. (2005); Klusa (1995); Mannhold et al. (1992); Nakayama & Kasoka (1996); Sridhar & Perumal (2005); Tewari et al. (2004); Tu et al. (2001).

Computing details top

Data collection: APEX2 (Bruker, 2003); cell refinement: SAINT (Bruker, 2003); data reduction: SAINT; program(s) used to solve structure: SIR2002 (Burla et al., 2003); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEP-3 (Farrugia, 1997) and DIAMOND (Brandenburg & Berndt, 2001); software used to prepare material for publication: WinGX (Farrugia, 1999).

Figures top
[Figure 1] Fig. 1. The structure of the title compound with the atomic labelling scheme. Displacement are drawn at the 50% probability level.
[Figure 2] Fig. 2. A diagram of the layered crystal packing of (I) viewed down the b axis. Hydrogen bonds are shown as dashed lines.
Diethyl 4-(4-bromophenyl)-2,6-dimethyl-1,4-dihydropyridine-3,5-dicarboxylate top
Crystal data top
C19H22BrNO4F(000) = 840
Mr = 408.28Dx = 1.505 Mg m−3
Monoclinic, P21/nMo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ynCell parameters from 8206 reflections
a = 10.0597 (5) Åθ = 2.3–27.5°
b = 7.4244 (4) ŵ = 2.30 mm−1
c = 24.3726 (13) ÅT = 295 K
β = 98.126 (2)°Prism, colourless
V = 1802.05 (16) Å30.15 × 0.11 × 0.1 mm
Z = 4
Data collection top
Bruker APEXII
diffractometer		Rint = 0.044
Graphite monochromatorθmax = 27.5°, θmin = 1.7°
CCD rotation images, thin slices, φ scans, and ωh = −12→13
19743 measured reflectionsk = −9→9
4132 independent reflectionsl = −31→30
3460 reflections with I > 2σ(I)
Refinement top
Refinement on F2Secondary atom site location: difference Fourier map
Least-squares matrix: fullHydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.027H-atom parameters constrained
wR(F2) = 0.093 w = 1/[σ2(Fo2) + (0.0459P)2 + 0.9623P]
where P = (Fo2 + 2Fc2)/3
S = 1.13(Δ/σ)max = 0.002
4132 reflectionsΔρmax = 0.55 e Å−3
230 parametersΔρmin = −0.33 e Å−3
0 restraintsExtinction correction: SHELXL97 (Sheldrick, 1997)
Primary atom site location: structure-invariant direct methodsExtinction coefficient: none
Crystal data top
C19H22BrNO4V = 1802.05 (16) Å3
Mr = 408.28Z = 4
Monoclinic, P21/nMo Kα radiation
a = 10.0597 (5) ŵ = 2.30 mm−1
b = 7.4244 (4) ÅT = 295 K
c = 24.3726 (13) Å0.15 × 0.11 × 0.1 mm
β = 98.126 (2)°
Data collection top
Bruker APEXII
diffractometer		3460 reflections with I > 2σ(I)
19743 measured reflectionsRint = 0.044
4132 independent reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0270 restraints
wR(F2) = 0.093H-atom parameters constrained
S = 1.13Δρmax = 0.55 e Å−3
4132 reflectionsΔρmin = −0.33 e Å−3
230 parameters
Special details top

Geometry. Bond distances, angles etc. have been calculated using the rounded fractional coordinates. All su's are estimated from the variances of the (full) variance-covariance matrix. The cell e.s.d.'s are taken into account in the estimation of distances, angles and torsion angles

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
xyzUiso*/Ueq
Br0.53359 (2)0.25548 (3)0.27107 (1)0.0231 (1)
O11.15604 (14)−0.0716 (2)0.14212 (6)0.0248 (5)
O21.07916 (15)0.2138 (2)0.13729 (6)0.0213 (4)
O30.72372 (13)0.42820 (18)0.00338 (6)0.0180 (4)
O40.57284 (14)0.24035 (17)−0.04326 (6)0.0181 (4)
N10.81110 (17)−0.1926 (2)0.02334 (7)0.0158 (4)
C11.0102 (2)−0.3304 (3)0.07312 (9)0.0204 (6)
C20.92482 (18)−0.1649 (3)0.06168 (8)0.0151 (5)
C30.95008 (18)0.0016 (3)0.08344 (8)0.0138 (5)
C40.84771 (18)0.1524 (3)0.07128 (7)0.0133 (5)
C50.75149 (18)0.1147 (3)0.01826 (7)0.0127 (5)
C60.73320 (18)−0.0549 (3)−0.00198 (7)0.0136 (5)
C70.63769 (19)−0.1155 (3)−0.05182 (8)0.0181 (6)
C80.68440 (19)0.2753 (2)−0.00735 (8)0.0130 (5)
C90.51398 (19)0.3921 (3)−0.07597 (8)0.0193 (6)
C100.5891 (2)0.4244 (3)−0.12397 (9)0.0303 (7)
C111.07165 (18)0.0371 (3)0.12318 (8)0.0169 (6)
C121.1835 (2)0.2660 (3)0.18190 (10)0.0264 (7)
C131.1395 (3)0.2357 (3)0.23741 (10)0.0292 (7)
C140.76975 (18)0.1802 (3)0.12001 (7)0.0137 (5)
C150.6847 (2)0.0454 (3)0.13475 (8)0.0184 (6)
C160.6134 (2)0.0666 (3)0.17933 (8)0.0201 (6)
C170.6288 (2)0.2243 (3)0.20965 (8)0.0170 (6)
C180.7117 (2)0.3610 (3)0.19590 (8)0.0208 (6)
C190.7813 (2)0.3375 (3)0.15105 (8)0.0193 (6)
H10.78782−0.301680.014860.0190*
H1A1.09448−0.312510.059730.0305*
H1B0.96477−0.431870.054620.0305*
H1C1.02581−0.352450.112310.0305*
H40.896370.263880.065920.0159*
H7A0.54706−0.10591−0.044010.0271*
H7B0.65646−0.23841−0.060210.0271*
H7C0.64872−0.04066−0.082990.0271*
H9A0.517860.49911−0.052950.0232*
H9B0.420470.36700−0.089500.0232*
H10A0.680670.45441−0.110410.0455*
H10B0.548070.52207−0.146010.0455*
H10C0.586620.31751−0.146240.0455*
H12A1.205040.392340.178000.0317*
H12B1.264030.196400.179410.0317*
H13A1.053960.292150.238230.0437*
H13B1.204460.286770.265790.0437*
H13C1.131920.108730.243750.0437*
H150.67545−0.060860.114350.0220*
H160.55656−0.023880.188530.0241*
H180.720770.467010.216400.0249*
H190.836730.429320.141630.0232*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Br0.0243 (1)0.0300 (2)0.0161 (1)0.0065 (1)0.0068 (1)−0.0015 (1)
O10.0172 (7)0.0324 (9)0.0236 (8)0.0037 (6)−0.0011 (6)0.0056 (6)
O20.0174 (7)0.0263 (8)0.0184 (8)−0.0045 (6)−0.0032 (6)−0.0026 (6)
O30.0208 (7)0.0123 (7)0.0201 (7)0.0007 (5)0.0004 (5)−0.0008 (5)
O40.0179 (7)0.0148 (7)0.0195 (8)−0.0010 (5)−0.0044 (6)0.0042 (5)
N10.0183 (8)0.0097 (7)0.0187 (8)−0.0010 (6)0.0002 (6)−0.0012 (6)
C10.0202 (10)0.0182 (10)0.0234 (11)0.0044 (8)0.0055 (8)0.0035 (8)
C20.0147 (9)0.0167 (10)0.0144 (9)0.0010 (7)0.0041 (7)0.0033 (7)
C30.0138 (8)0.0164 (9)0.0117 (9)0.0003 (7)0.0032 (7)0.0016 (7)
C40.0149 (8)0.0124 (9)0.0122 (9)−0.0023 (7)0.0011 (7)−0.0003 (7)
C50.0132 (8)0.0133 (9)0.0118 (9)−0.0005 (7)0.0027 (7)0.0008 (7)
C60.0151 (9)0.0149 (10)0.0110 (9)−0.0006 (7)0.0027 (7)0.0013 (7)
C70.0215 (10)0.0153 (10)0.0163 (10)−0.0016 (8)−0.0011 (8)−0.0030 (7)
C80.0137 (9)0.0157 (10)0.0103 (9)−0.0004 (7)0.0044 (7)−0.0002 (7)
C90.0176 (9)0.0165 (10)0.0218 (10)0.0019 (8)−0.0043 (8)0.0053 (8)
C100.0378 (13)0.0325 (13)0.0202 (11)0.0103 (10)0.0023 (9)0.0078 (9)
C110.0144 (9)0.0242 (11)0.0127 (9)−0.0024 (7)0.0038 (7)0.0024 (7)
C120.0195 (10)0.0386 (14)0.0198 (11)−0.0103 (9)−0.0013 (9)−0.0050 (9)
C130.0273 (12)0.0371 (14)0.0226 (12)−0.0052 (9)0.0020 (9)−0.0058 (9)
C140.0135 (9)0.0157 (9)0.0111 (8)0.0013 (7)−0.0007 (7)0.0003 (7)
C150.0242 (10)0.0152 (10)0.0162 (9)−0.0022 (8)0.0048 (8)−0.0034 (7)
C160.0222 (10)0.0206 (10)0.0180 (10)−0.0028 (8)0.0047 (8)0.0007 (8)
C170.0163 (9)0.0242 (11)0.0106 (9)0.0064 (7)0.0027 (7)0.0003 (7)
C180.0226 (10)0.0185 (10)0.0210 (10)−0.0001 (8)0.0022 (8)−0.0070 (8)
C190.0202 (10)0.0173 (10)0.0205 (10)−0.0025 (8)0.0028 (8)−0.0032 (8)
Geometric parameters (Å, º) top
Br—C171.902 (2)C16—C171.382 (3)
O1—C111.214 (2)C17—C181.385 (3)
O2—C111.356 (3)C18—C191.390 (3)
O2—C121.453 (3)C1—H1A0.9600
O3—C81.218 (2)C1—H1B0.9600
O4—C81.347 (2)C1—H1C0.9600
O4—C91.457 (3)C4—H40.9800
N1—C21.386 (3)C7—H7A0.9600
N1—C61.380 (3)C7—H7B0.9600
N1—H10.8600C7—H7C0.9600
C1—C21.503 (3)C9—H9A0.9700
C2—C31.355 (3)C9—H9B0.9700
C3—C111.473 (3)C10—H10A0.9600
C3—C41.522 (3)C10—H10B0.9600
C4—C141.527 (2)C10—H10C0.9600
C4—C51.527 (2)C12—H12A0.9700
C5—C61.355 (3)C12—H12B0.9700
C5—C81.466 (3)C13—H13A0.9600
C6—C71.507 (3)C13—H13B0.9600
C9—C101.499 (3)C13—H13C0.9600
C12—C131.499 (3)C15—H150.9300
C14—C191.387 (3)C16—H160.9300
C14—C151.396 (3)C18—H180.9300
C15—C161.393 (3)C19—H190.9300
C11—O2—C12117.15 (16)H1A—C1—H1C110.00
C8—O4—C9116.32 (14)H1B—C1—H1C109.00
C2—N1—C6123.64 (17)C3—C4—H4108.00
C6—N1—H1118.00C5—C4—H4108.00
C2—N1—H1118.00C14—C4—H4108.00
N1—C2—C3119.37 (18)C6—C7—H7A109.00
N1—C2—C1113.54 (18)C6—C7—H7B109.00
C1—C2—C3127.07 (18)C6—C7—H7C109.00
C4—C3—C11118.21 (18)H7A—C7—H7B109.00
C2—C3—C4120.71 (17)H7A—C7—H7C109.00
C2—C3—C11120.87 (19)H7B—C7—H7C109.00
C3—C4—C14110.84 (16)O4—C9—H9A110.00
C3—C4—C5111.13 (17)O4—C9—H9B110.00
C5—C4—C14110.44 (15)C10—C9—H9A110.00
C4—C5—C8114.20 (18)C10—C9—H9B110.00
C4—C5—C6121.03 (18)H9A—C9—H9B108.00
C6—C5—C8124.76 (16)C9—C10—H10A109.00
N1—C6—C7113.35 (18)C9—C10—H10B109.00
C5—C6—C7127.52 (18)C9—C10—H10C109.00
N1—C6—C5119.10 (16)H10A—C10—H10B109.00
O4—C8—C5114.28 (14)H10A—C10—H10C109.00
O3—C8—O4122.29 (16)H10B—C10—H10C109.00
O3—C8—C5123.41 (18)O2—C12—H12A109.00
O4—C9—C10109.88 (16)O2—C12—H12B109.00
O2—C11—C3110.57 (17)C13—C12—H12A109.00
O1—C11—C3127.0 (2)C13—C12—H12B109.00
O1—C11—O2122.40 (18)H12A—C12—H12B108.00
O2—C12—C13111.17 (18)C12—C13—H13A109.00
C15—C14—C19118.05 (17)C12—C13—H13B109.00
C4—C14—C15120.27 (18)C12—C13—H13C109.00
C4—C14—C19121.69 (18)H13A—C13—H13B109.00
C14—C15—C16121.44 (19)H13A—C13—H13C109.00
C15—C16—C17118.8 (2)H13B—C13—H13C109.00
Br—C17—C18119.27 (16)C14—C15—H15119.00
Br—C17—C16119.56 (16)C16—C15—H15119.00
C16—C17—C18121.17 (19)C15—C16—H16121.00
C17—C18—C19119.1 (2)C17—C16—H16121.00
C14—C19—C18121.46 (19)C17—C18—H18120.00
C2—C1—H1A109.00C19—C18—H18120.00
C2—C1—H1B109.00C14—C19—H19119.00
C2—C1—H1C109.00C18—C19—H19119.00
H1A—C1—H1B109.00
C11—O2—C12—C13−83.5 (2)C14—C4—C5—C6−102.3 (2)
C12—O2—C11—O1−7.9 (3)C14—C4—C5—C878.0 (2)
C12—O2—C11—C3171.77 (16)C3—C4—C14—C15−65.5 (2)
C8—O4—C9—C1080.4 (2)C3—C4—C14—C19114.0 (2)
C9—O4—C8—O310.3 (3)C5—C4—C14—C1558.1 (2)
C9—O4—C8—C5−171.06 (15)C5—C4—C14—C19−122.3 (2)
C6—N1—C2—C1−166.26 (17)C4—C5—C6—C7176.77 (17)
C6—N1—C2—C312.1 (3)C8—C5—C6—N1174.40 (17)
C2—N1—C6—C5−12.9 (3)C8—C5—C6—C7−3.5 (3)
C2—N1—C6—C7165.30 (17)C4—C5—C8—O317.5 (3)
C1—C2—C3—C11−0.3 (3)C4—C5—C8—O4−161.12 (16)
N1—C2—C3—C46.9 (3)C6—C5—C8—O3−162.23 (19)
N1—C2—C3—C11−178.42 (17)C6—C5—C8—O419.1 (3)
C1—C2—C3—C4−174.97 (18)C4—C5—C6—N1−5.4 (3)
C2—C3—C4—C14101.3 (2)C4—C14—C15—C16179.40 (18)
C11—C3—C4—C5163.28 (17)C19—C14—C15—C16−0.2 (3)
C11—C3—C4—C14−73.5 (2)C4—C14—C19—C18−178.99 (18)
C2—C3—C11—O1−3.2 (3)C15—C14—C19—C180.6 (3)
C2—C3—C11—O2177.10 (17)C14—C15—C16—C17−0.6 (3)
C4—C3—C11—O1171.59 (19)C15—C16—C17—Br−179.49 (15)
C4—C3—C11—O2−8.1 (2)C15—C16—C17—C181.0 (3)
C2—C3—C4—C5−21.9 (2)Br—C17—C18—C19179.87 (15)
C3—C4—C5—C621.2 (2)C16—C17—C18—C19−0.6 (3)
C3—C4—C5—C8−158.58 (16)C17—C18—C19—C14−0.2 (3)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N1—H1···O3i0.862.112.969 (2)173
C4—H4···O30.982.472.811 (2)100
Symmetry code: (i) x, y−1, z.

Experimental details

Crystal data
Chemical formulaC19H22BrNO4
Mr408.28
Crystal system, space groupMonoclinic, P21/n
Temperature (K)295
a, b, c (Å)10.0597 (5), 7.4244 (4), 24.3726 (13)
β (°) 98.126 (2)
V (Å3)1802.05 (16)
Z4
Radiation typeMo Kα
µ (mm−1)2.30
Crystal size (mm)0.15 × 0.11 × 0.1
Data collection
DiffractometerBruker APEXII
Absorption correction–
No. of measured, independent and
observed [I > 2σ(I)] reflections		19743, 4132, 3460
Rint0.044
(sin θ/λ)max (Å−1)0.650
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.027, 0.093, 1.13
No. of reflections4132
No. of parameters230
H-atom treatmentH-atom parameters constrained
Δρmax, Δρmin (e Å−3)0.55, −0.33

Computer programs: APEX2 (Bruker, 2003), SAINT (Bruker, 2003), SAINT, SIR2002 (Burla et al., 2003), SHELXL97 (Sheldrick, 1997), ORTEP-3 (Farrugia, 1997) and DIAMOND (Brandenburg & Berndt, 2001), WinGX (Farrugia, 1999).

Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N1—H1···O3i0.862.112.969 (2)173
C4—H4···O30.982.472.811 (2)100
Symmetry code: (i) x, y−1, z.
 

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