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The title compound, C19H18BrNO3, has potential calcium modulatory properties. The 1,4-di­hydro­pyridine ring has a very shallow boat conformation and is one of the most planar examples of this moiety. The 2-bromo­phenyl substituent is in the axial synperiplanar orientation. The quinoline ring has a half-chair conformation, with the unusual arrangement of the out-of-plane atom being on the opposite side of the ring plane to the bromo­phenyl substituent. The mol­ecules are linked into chains by intermolecular hydrogen bonds.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S0108270199015255/sk1350sup1.cif
Contains datablocks global, I

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S0108270199015255/sk1350Isup2.hkl
Contains datablock I

CCDC reference: 143255

Comment top

Dihydropyridine calcium entry blockers have been widely explored as cardiovascular agents. Nifedipine is the prototype of 1,4-dihydropyridine (1,4-DHP) derivatives and has been approved as a clinical agent for antianginal and antihypertensive therapy (Janis & Triggle, 1983; Goldmann et al., 1990). It has been proposed (Fossheim, 1986; Goldmann & Stoltefuss, 1991) that the activity of ester derivatives of 1,4-DHP compounds may, in part, be associated with the orientation of the ester carbonyl groups. In order to fix these carbonyl groups in the antiperiplanar position with respect to the 1,4-DHP ring double-bond so that the activity of compounds with this arrangement can be studied, the 1,4-DHP structure can be anellated and such compounds have been obtained by the introduction of the 1,4-DHP moiety to condensed systems (Rose & Dräger, 1992). These derivatives possess similar activities to nifedipine. In addition, biotransformation studies on 1,4-DHP derivatives show that these compounds convert to lactone analogues in vivo and these latter compounds were also found to be active as agonists or antagonists.

The title compound, (I), has been synthesized because it is thought to be a possible metabolite of the ester, (II), which we have previously synthesized. The structure of the 2-fluorophenyl ethyl ester analogue of (II) has already been reported (Linden et al., 1998). The crystal structure of (I) has now been determined in order to elucidate the specific conformational properties of the molecule. \scheme

The 1,4-DHP ring in the structure of (I) has a very shallow boat conformation, with N1 and C4 being 0.060 (6) and 0.095 (7) Å, respectively, from the plane defined by C2, C3, C4a and C8a. The maximum deviation of these latter four atoms from their mean plane is 0.003 (2) Å for C2. The 2-bromophenyl ring occupies a pseudo-axial position and thereby lies above the 1,4-DHP boat. The plane of the 2-bromophenyl ring is almost parallel to the N1···C4 axis, with an N1···C4—C11—C16 torsion angle of -2.5 (6)°, which is sterically the most favourable orientation. The bromo substituent lies above the C4—H bond in a synperiplanar orientation and not over the centre of the boat.

The conformations of 4-aryl-1,4-DHP rings have been discussed previously (Goldmann & Stoltefuss, 1991; Linden et al., 1998). The orientation of the 2-bromophenyl ring in (I) is consistent with related structures, but the 1,4-DHP ring has one of the shallowest boat conformations seen so far. The Cambridge Structural Database (CSD, April 1999 release; Allen & Kennard, 1993) contains 75 entries with the 4-aryl-1,4-DHP moiety, excluding 4,4-disubstituted derivatives, and all of them have the shallow boat conformation with the aryl group in an axial position. With the exception of one nearly planar case (Pastor et al., 1994), C4 is found in the range of 0.11–0.42 Å from the plane defined by C2, C3, C4a and C8a, with the most frequently occurring values being around 0.30 Å (Linden et al., 1998). The deviations shown by N1 are generally smaller and the range is spread fairly evenly over 0.04–0.19 Å. While the deviation of N1 from the above-defined plane in (I) is within the normal range, the deviation of C4 is well outside the range and indicates the near planarity of this end of the 1,4-DHP ring. Another measure of the shallowness of the boat conformation in 1,4-DHP rings is the sum of the magnitudes of the six intraring torsion angles, P, around the ring (Fossheim et al., 1988). For (I), P is only 29 (2)°, compared with a range for P of 51–122° found for the structures of 25 1,4-DHP compounds (Fossheim et al., 1988). Such a severe flattening might have significant implications for the calcium modulatory properties of (I), as it has been suggested (Fossheim et al., 1982, 1988) that the most active compounds in the nifedipine and nisoldipine series possess the shallowest boat conformations. The calcium modulatory and biotransformation properties of (I) are being studied and will be reported later.

The oxocyclohexene ring in (I) has an envelope conformation, in which C7 is 0.581 (8) Å from the plane defined by C4a, C5, C6, C8 and C8a. The maximum deviation of these latter five atoms from their mean plane is 0.033 (4) Å for C5. The puckering parameters (Cremer & Pople, 1975) are Q = 0.423 (6) Å, θ = 50.5 (8)° and ϕ2 = 112.8 (10)°. For an ideal envelope, θ and ϕ2 are 54.7 and n × 60°, respectively (define n). The envelope flap of the ring flips down on the opposite side of the ring plane to the 2-bromophenyl substituent of the adjacent 1,4-DHP ring. The CSD contains 16 entries for structures involving the 5-oxoquinoline or 1,8-dioxoacridine moieties and it is found that C7 is always the out-of-plane atom. This is a consequence of the π-electron conjugation between the oxo group and the cyclohexene double bond, which constrains all other atoms in the cyclohexene ring to a planar conformation. However, in 13 of these structures, C7 lies on the same side of the ring plane as the substituent at C4 of the 1,4-DHP ring, so the arrangement in (I) is uncommon in this respect.

Most of the bond lengths and angles in (I) have normal values. The only irregularity is an enlarged angle for O10—C10—C3 and a correspondingly smaller angle for O9—C10—O10 (Table 1). The lactone ring has a very shallow envelope conformation, with C9 acting as the envelope flap but lying only 0.092 (7) Å from the plane defined by C2, C3, O9 and C10. The maximum deviation of these latter four atoms from their mean plane is 0.012 (3) Å for C10. Intermolecular hydrogen bonds between the amine group and the lactone carbonyl O atom, O10, of a neighbouring molecule (Table 2) link the molecules into infinite one-dimensional zigzag chains which run parallel to the y axis and have the graph-set motif of C(6) (Bernstein et al., 1995).

Experimental top

Compound (I) was obtained by stirring equimolar amounts of 4-(2-bromophenyl)-1,4,5,6,7,8-hexahydro-3-methoxycarbonyl-5-oxo-2,6,6- trimethylquinoline, (II), with pyridinium bromide perbromide in chloroform for 1 h at 273 K. The mixture was then refluxed for 24 h. The solvent was removed in vacuo and the precipitate was recrystallized from ethanol (m.p. 575 K). The product was characterized by IR, 1H– and 13C-NMR, mass spectroscopic and elemental analyses. Single crystals were obtained by recrystallization from dimethylsulfoxide.

Refinement top

Please provide details of H-atom treatment

Computing details top

Data collection: MSC/AFC Diffractometer Control Software (Molecular Structure Corporation, 1991); cell refinement: MSC/AFC Diffractometer Control Software; data reduction: TEXSAN (Molecular Structure Corporation, 1997); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997a); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997b); molecular graphics: ORTEPII (Johnson, 1976); software used to prepare material for publication: SHELXL97.

Figures top
[Figure 1] Fig. 1. View of the molecule of (I) showing the atom-labelling scheme. Displacement ellipsoids are drawn at the 50% probability level and H atoms are represented by spheres of arbitrary size.
(±)-9-(2-Bromophenyl)-7,7-dimethyl-1,3,4,5,6,7,8,9-octahydrofuro[3,4-b]quinoline-1,8-dione top
Crystal data top
C19H18BrNO3Dx = 1.541 Mg m3
Mr = 388.26Melting point: 575 K
Monoclinic, P21/cMo Kα radiation, λ = 0.71069 Å
a = 11.724 (5) ÅCell parameters from 23 reflections
b = 10.911 (4) Åθ = 18.5–20.0°
c = 14.218 (6) ŵ = 2.48 mm1
β = 113.11 (4)°T = 180 K
V = 1672.9 (12) Å3Irregular prism, pale yellow
Z = 40.30 × 0.30 × 0.21 mm
F(000) = 792
Data collection top
Rigaku AFC-5R
diffractometer
2018 reflections with I > 2σ(I)
Radiation source: Rigaku rotating anode generatorRint = 0.091
Graphite monochromatorθmax = 27.5°, θmin = 2.5°
ω/2θ scansh = 015
Absorption correction: ψ-scan
(North et al., 1968)
k = 014
Tmin = 0.536, Tmax = 0.609l = 1817
4239 measured reflections3 standard reflections every 150 reflections
3842 independent reflections intensity decay: none
Refinement top
Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullHydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.059H-atom parameters constrained
wR(F2) = 0.165 w = 1/[σ2(Fo2) + (0.0831P)2]
where P = (Fo2 + 2Fc2)/3
S = 0.97(Δ/σ)max = 0.001
3842 reflectionsΔρmax = 0.87 e Å3
220 parametersΔρmin = 0.74 e Å3
0 restraints
Crystal data top
C19H18BrNO3V = 1672.9 (12) Å3
Mr = 388.26Z = 4
Monoclinic, P21/cMo Kα radiation
a = 11.724 (5) ŵ = 2.48 mm1
b = 10.911 (4) ÅT = 180 K
c = 14.218 (6) Å0.30 × 0.30 × 0.21 mm
β = 113.11 (4)°
Data collection top
Rigaku AFC-5R
diffractometer
2018 reflections with I > 2σ(I)
Absorption correction: ψ-scan
(North et al., 1968)
Rint = 0.091
Tmin = 0.536, Tmax = 0.6093 standard reflections every 150 reflections
4239 measured reflections intensity decay: none
3842 independent reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0590 restraints
wR(F2) = 0.165H-atom parameters constrained
S = 0.97Δρmax = 0.87 e Å3
3842 reflectionsΔρmin = 0.74 e Å3
220 parameters
Special details top

Experimental. The very irregular crystal form did not facilitate face-indexing for an analytical absorption correction. This also resulted in the quoted crystal dimensions being very approximate and may account for some of the discrepancy between the experimental and predicted values of Tmin and Tmx.

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.

Least-squares planes (x,y,z in crystal coordinates) and deviations from them (* indicates atom used to define plane)

9.4537 (0.0170) x + 5.6831 (0.0285) y - 8.1644 (0.0326) z = 4.6101 (0.0103)

* -0.0026 (0.0023) C2 * 0.0025 (0.0022) C3 * -0.0024 (0.0021) C4A * 0.0025 (0.0022) C8A 0.0600 (0.0064) N1 0.0948 (0.0071) C4

Rms deviation of fitted atoms = 0.0025

9.5916 (0.0182) x + 5.6649 (0.0233) y - 7.7994 (0.0234) z = 4.6193 (0.0074)

Angle to previous plane (with approximate e.s.d.) = 2.01 (0.35)

* 0.0190 (0.0032) C4A * -0.0327 (0.0035) C5 * 0.0230 (0.0026) C6 * -0.0147 (0.0025) C8 * 0.0055 (0.0034) C8A -0.5805 (0.0075) C7

Rms deviation of fitted atoms = 0.0210

9.4921 (0.0175) x + 5.5459 (0.0290) y - 8.3570 (0.0330) z = 4.5729 (0.0131)

Angle to previous plane (with approximate e.s.d.) = 2.77 (0.36)

* 0.0073 (0.0016) C2 * -0.0117 (0.0025) C3 * -0.0074 (0.0016) O9 * 0.0118 (0.0026) C10 - 0.0924 (0.0072) C9

Rms deviation of fitted atoms = 0.0098

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
Br10.07276 (7)0.82218 (5)0.10441 (5)0.0513 (2)
O20.2878 (4)0.5733 (3)0.1869 (3)0.0421 (10)
O90.1074 (3)0.5731 (3)0.2880 (2)0.0301 (8)
O100.1004 (3)0.7311 (3)0.1864 (3)0.0322 (8)
N10.1497 (4)0.3785 (4)0.1352 (3)0.0269 (9)
H10.16020.31960.17340.046 (17)*
C20.0571 (4)0.4626 (4)0.1763 (4)0.0235 (10)
C30.0428 (4)0.5611 (4)0.1248 (4)0.0246 (10)
C40.1284 (4)0.5909 (4)0.0163 (3)0.0218 (10)
H40.07800.59970.02600.026*
C4a0.2187 (4)0.4835 (4)0.0254 (3)0.0244 (11)
C50.2987 (5)0.4888 (4)0.1343 (4)0.0274 (11)
C60.3999 (5)0.3911 (5)0.1806 (4)0.0313 (12)
C70.3605 (5)0.2702 (5)0.1218 (4)0.0322 (12)
H7a0.43140.21260.14630.039*
H7B0.29250.23360.13720.039*
C80.3175 (5)0.2846 (5)0.0068 (4)0.0332 (12)
H8a0.39020.30050.01040.040*
H8B0.27850.20730.02700.040*
C8a0.2267 (4)0.3871 (4)0.0330 (4)0.0238 (11)
C90.0424 (5)0.4580 (4)0.2804 (4)0.0288 (11)
H9a0.00720.45240.33310.035*
H9B0.09820.38740.28770.035*
C100.0583 (4)0.6308 (5)0.1962 (4)0.0273 (11)
C110.1971 (4)0.7123 (4)0.0128 (3)0.0225 (10)
C120.1829 (5)0.8182 (5)0.0349 (3)0.0275 (11)
C130.2431 (5)0.9268 (5)0.0325 (4)0.0309 (12)
H130.23110.99770.06630.037*
C140.3212 (5)0.9307 (5)0.0198 (4)0.0341 (12)
H140.36411.00400.02140.041*
C150.3360 (5)0.8261 (5)0.0698 (4)0.0343 (12)
H150.38780.82860.10710.041*
C160.2758 (5)0.7187 (4)0.0656 (4)0.0268 (11)
H160.28810.64770.09920.032*
C170.5194 (5)0.4417 (5)0.1740 (4)0.0429 (14)
H17a0.53930.52160.20800.064*
H17B0.50690.45090.10200.064*
H17C0.58800.38460.20760.064*
C180.4222 (5)0.3685 (6)0.2929 (4)0.0409 (14)
H18a0.34640.33590.29710.061*
H18B0.44460.44580.33080.061*
H18C0.48970.30930.32260.061*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Br10.0829 (5)0.0281 (3)0.0717 (5)0.0024 (3)0.0614 (4)0.0064 (3)
O20.059 (3)0.036 (2)0.028 (2)0.013 (2)0.0137 (19)0.0053 (17)
O90.031 (2)0.0245 (18)0.0295 (19)0.0012 (16)0.0063 (16)0.0052 (15)
O100.040 (2)0.0214 (17)0.039 (2)0.0066 (17)0.0192 (18)0.0118 (16)
N10.032 (2)0.020 (2)0.027 (2)0.0039 (19)0.009 (2)0.0027 (18)
C20.029 (3)0.018 (2)0.025 (3)0.001 (2)0.012 (2)0.004 (2)
C30.027 (3)0.020 (2)0.029 (3)0.001 (2)0.013 (2)0.006 (2)
C40.030 (3)0.017 (2)0.023 (3)0.002 (2)0.016 (2)0.0006 (19)
C4a0.029 (3)0.021 (2)0.024 (3)0.002 (2)0.012 (2)0.003 (2)
C50.038 (3)0.021 (2)0.026 (3)0.002 (2)0.015 (2)0.001 (2)
C60.039 (3)0.029 (3)0.028 (3)0.008 (2)0.015 (3)0.001 (2)
C70.039 (3)0.022 (2)0.033 (3)0.013 (2)0.012 (3)0.006 (2)
C80.042 (3)0.020 (2)0.035 (3)0.007 (2)0.012 (3)0.002 (2)
C8a0.025 (3)0.022 (2)0.026 (3)0.000 (2)0.011 (2)0.002 (2)
C90.036 (3)0.020 (2)0.031 (3)0.000 (2)0.014 (2)0.008 (2)
C100.025 (3)0.031 (3)0.029 (3)0.004 (2)0.013 (2)0.007 (2)
C110.025 (3)0.022 (2)0.019 (2)0.002 (2)0.007 (2)0.0010 (19)
C120.033 (3)0.027 (2)0.022 (2)0.003 (2)0.011 (2)0.001 (2)
C130.040 (3)0.020 (2)0.032 (3)0.000 (2)0.013 (3)0.001 (2)
C140.038 (3)0.022 (3)0.039 (3)0.006 (2)0.012 (3)0.009 (2)
C150.033 (3)0.033 (3)0.040 (3)0.002 (3)0.018 (3)0.008 (3)
C160.029 (3)0.021 (2)0.031 (3)0.001 (2)0.012 (2)0.000 (2)
C170.038 (3)0.045 (4)0.047 (4)0.002 (3)0.019 (3)0.007 (3)
C180.042 (3)0.050 (3)0.027 (3)0.012 (3)0.010 (3)0.002 (3)
Geometric parameters (Å, º) top
Br1—C121.910 (5)C7—H7B0.99
O2—C51.225 (5)C8—C8a1.493 (7)
O9—C101.357 (6)C8—H8a0.99
O9—C91.451 (6)C8—H8B0.99
O10—C101.231 (6)C9—H9a0.99
N1—C21.365 (6)C9—H9B0.99
N1—C8a1.381 (6)C11—C121.383 (6)
N1—H10.88C11—C161.402 (6)
C2—C31.347 (6)C12—C131.386 (7)
C2—C91.483 (7)C13—C141.389 (7)
C3—C41.510 (7)C13—H130.95
C3—C101.439 (7)C14—C151.391 (7)
C4—C4a1.533 (6)C14—H140.95
C4—C111.541 (6)C15—C161.381 (7)
C4—H41.00C15—H150.95
C4a—C8a1.366 (6)C16—H160.95
C4a—C51.463 (7)C17—H17a0.98
C5—C61.537 (7)C17—H17B0.98
C6—C71.533 (7)C17—H17C0.98
C6—C181.533 (7)C18—H18a0.98
C6—C171.544 (7)C18—H18B0.98
C7—C81.519 (7)C18—H18C0.98
C7—H7a0.99
C10—O9—C9108.5 (4)C4a—C8a—C8123.7 (4)
C2—N1—C8a119.1 (4)N1—C8a—C8115.0 (4)
C2—N1—H1120.5O9—C9—C2103.3 (4)
C8a—N1—H1120.5O9—C9—H9a111.1
C3—C2—N1123.5 (5)C2—C9—H9a111.1
C3—C2—C9110.6 (4)O9—C9—H9B111.1
N1—C2—C9125.9 (4)C2—C9—H9B111.1
C2—C3—C10106.4 (4)H9a—C9—H9B109.1
C2—C3—C4123.5 (4)O10—C10—O9118.9 (4)
C10—C3—C4129.8 (4)O10—C10—C3130.2 (5)
C3—C4—C4a108.2 (4)O9—C10—C3110.8 (4)
C3—C4—C11110.3 (4)C12—C11—C16116.9 (4)
C4a—C4—C11111.8 (4)C12—C11—C4124.9 (4)
C3—C4—H4108.8C16—C11—C4118.1 (4)
C4a—C4—H4108.8C11—C12—C13122.8 (4)
C11—C4—H4108.8C11—C12—Br1120.6 (4)
C8a—C4a—C5120.4 (4)C13—C12—Br1116.6 (4)
C8a—C4a—C4123.7 (4)C12—C13—C14119.2 (5)
C5—C4a—C4115.9 (4)C12—C13—H13120.4
O2—C5—C4a119.9 (5)C14—C13—H13120.4
O2—C5—C6120.6 (4)C13—C14—C15119.3 (5)
C4a—C5—C6119.5 (4)C13—C14—H14120.3
C7—C6—C18108.8 (4)C15—C14—H14120.3
C7—C6—C5110.3 (4)C16—C15—C14120.4 (5)
C18—C6—C5110.2 (4)C16—C15—H15119.8
C7—C6—C17111.1 (4)C14—C15—H15119.8
C18—C6—C17109.5 (4)C15—C16—C11121.4 (4)
C5—C6—C17107.0 (4)C15—C16—H16119.3
C8—C7—C6113.6 (4)C11—C16—H16119.3
C8—C7—H7a108.8C6—C17—H17a109.5
C6—C7—H7a108.8C6—C17—H17B109.5
C8—C7—H7B108.8H17a—C17—H17B109.5
C6—C7—H7B108.8C6—C17—H17C109.5
H7a—C7—H7B107.7H17a—C17—H17C109.5
C8a—C8—C7111.8 (4)H17B—C17—H17C109.5
C8a—C8—H8a109.3C6—C18—H18a109.5
C7—C8—H8a109.3C6—C18—H18B109.5
C8a—C8—H8B109.3H18a—C18—H18B109.5
C7—C8—H8B109.3C6—C18—H18C109.5
H8a—C8—H8B107.9H18a—C18—H18C109.5
C4a—C8a—N1121.3 (4)H18B—C18—H18C109.5
C8a—N1—C2—C36.2 (7)C4—C4a—C8a—C8177.9 (4)
C8a—N1—C2—C9172.1 (4)C4a—C8a—N1—C25.5 (7)
N1—C2—C3—C10175.8 (4)C2—N1—C8a—C8174.7 (4)
C9—C2—C3—C105.6 (5)C4a—C5—C6—C729.2 (6)
N1—C2—C3—C40.8 (7)C4a—C8a—C8—C723.5 (7)
C9—C2—C3—C4179.3 (4)C7—C8—C8a—N1156.8 (4)
C2—C3—C4—C4a7.1 (6)C10—O9—C9—C25.0 (5)
C10—C3—C4—C4a179.2 (4)C3—C2—C9—O96.7 (5)
C2—C3—C4—C11115.5 (5)N1—C2—C9—O9174.8 (4)
C10—C3—C4—C1158.2 (6)C9—O9—C10—O10179.8 (4)
C3—C4—C4a—C8a7.6 (6)C9—O9—C10—C32.0 (5)
C11—C4—C4a—C8a114.1 (5)C2—C3—C10—O10175.2 (5)
C3—C4—C4a—C5172.4 (4)C4—C3—C10—O100.5 (8)
C11—C4—C4a—C565.9 (5)C2—C3—C10—O92.3 (5)
C8a—C4a—C5—O2177.4 (4)C4—C3—C10—O9176.9 (4)
C4—C4a—C5—O22.6 (7)C3—C4—C11—C12114.8 (5)
C8a—C4a—C5—C65.4 (7)C4a—C4—C11—C12124.7 (5)
C4—C4a—C5—C6174.6 (4)C3—C4—C11—C1662.1 (5)
O2—C5—C6—C7153.6 (4)C4a—C4—C11—C1658.3 (5)
O2—C5—C6—C1833.5 (7)C16—C11—C12—C130.4 (7)
C4a—C5—C6—C18149.3 (5)C4—C11—C12—C13177.4 (4)
O2—C5—C6—C1785.4 (6)C16—C11—C12—Br1177.4 (3)
C4a—C5—C6—C1791.8 (5)C4—C11—C12—Br10.5 (6)
C18—C6—C7—C8171.5 (4)C11—C12—C13—C140.1 (8)
C5—C6—C7—C850.6 (6)Br1—C12—C13—C14177.9 (4)
C17—C6—C7—C867.9 (6)C12—C13—C14—C150.9 (8)
C6—C7—C8—C8a48.0 (6)C13—C14—C15—C161.5 (8)
C5—C4a—C8a—N1178.1 (4)C14—C15—C16—C111.1 (8)
C4—C4a—C8a—N11.8 (7)C12—C11—C16—C150.2 (7)
C5—C4a—C8a—C82.1 (7)C4—C11—C16—C15177.0 (4)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N1—H1···O10i0.882.072.864 (5)149
Symmetry code: (i) x, y1/2, z1/2.

Experimental details

Crystal data
Chemical formulaC19H18BrNO3
Mr388.26
Crystal system, space groupMonoclinic, P21/c
Temperature (K)180
a, b, c (Å)11.724 (5), 10.911 (4), 14.218 (6)
β (°) 113.11 (4)
V3)1672.9 (12)
Z4
Radiation typeMo Kα
µ (mm1)2.48
Crystal size (mm)0.30 × 0.30 × 0.21
Data collection
DiffractometerRigaku AFC-5R
diffractometer
Absorption correctionψ-scan
(North et al., 1968)
Tmin, Tmax0.536, 0.609
No. of measured, independent and
observed [I > 2σ(I)] reflections
4239, 3842, 2018
Rint0.091
(sin θ/λ)max1)0.651
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.059, 0.165, 0.97
No. of reflections3842
No. of parameters220
H-atom treatmentH-atom parameters constrained
Δρmax, Δρmin (e Å3)0.87, 0.74

Computer programs: MSC/AFC Diffractometer Control Software (Molecular Structure Corporation, 1991), MSC/AFC Diffractometer Control Software, TEXSAN (Molecular Structure Corporation, 1997), SHELXS97 (Sheldrick, 1997a), SHELXL97 (Sheldrick, 1997b), ORTEPII (Johnson, 1976), SHELXL97.

Selected geometric parameters (Å, º) top
O9—C101.357 (6)C3—C101.439 (7)
O9—C91.451 (6)C4—C4a1.533 (6)
O10—C101.231 (6)C4a—C8a1.366 (6)
N1—C21.365 (6)C4a—C51.463 (7)
N1—C8a1.381 (6)C5—C61.537 (7)
C2—C31.347 (6)C6—C71.533 (7)
C2—C91.483 (7)C7—C81.519 (7)
C3—C41.510 (7)C8—C8a1.493 (7)
O10—C10—O9118.9 (4)O10—C10—C3130.2 (5)
C8a—N1—C2—C36.2 (7)C4—C4a—C8a—N11.8 (7)
N1—C2—C3—C40.8 (7)C4a—C8a—N1—C25.5 (7)
C2—C3—C4—C4a7.1 (6)C4a—C5—C6—C729.2 (6)
C3—C4—C4a—C8a7.6 (6)C4a—C8a—C8—C723.5 (7)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N1—H1···O10i0.882.072.864 (5)149
Symmetry code: (i) x, y1/2, z1/2.
 

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