organic compounds
(1R,2R)-8-Bromo-1-[(E)-2-(4-bromophenyl)ethenyl]-2-nitro-1,2-dihydronaphtho[2,1-b]furan
aCatalytic Hydrogenation Research Center, Zhejiang University of Technology, Hangzhou, 310014, People's Republic of China
*Correspondence e-mail: wangyifeng@zjut.edu.cn
The title compound,C20H13Br2NO3, contains the dihydrobenzofuran moiety, which is present in the physiologically active components of many medicinal plants. The naphthyl ring system is nearly perpendicular to the phenyl ring, while the mean plane of the double bond is almost coplanar with the phenyl ring [dihedral angles of 79.14 (3) and 13.56 (1)°, respectively]. The nitro group and bromobenzene alkenyl group are trans to one another on opposite sides of the furan ring. There are two stereogenic centres, and each has the R configuration. In the crystal, there are very weak intermolecular C—H⋯Br interactions.
Keywords: crystal structure; dihydrobenzofuran; C—H⋯Br interactions.
CCDC reference: 1470708
Structure description
The title compound has a dihydrobenzofuran skeleton, which is the effective physiologically active component in many medicinal plants(Ohkawa et al. 1997; Snyder et al., 2011). The molecular structure of the title compound is shown in Fig. 1. The five-membered ring involving C9/C10/C11/C12/O1adopts an and is characterized by torsion angle values of −140.9 (6) and −18.7 (7)° for C13—C12—C11—N1 and C10—C12—C11—O1, respectively. The naphthyl group is nearly perpendicular to the phenyl ring, while the mean plane through the double bond and its attached substituents is almost coplanar with the phenyl ring [dihedral angles of 79.14 (3) and 13.56 (1)°, respectively]. Furthermore, the C12—C10—C9 and C10—C9—O1 bond angles are 109.7 (5)° and 112.0 (5)°, respectively. The nitro group and bromobenzene alkenyl group are mutually trans to one another, on opposite sides of the furan ring. The molecule possesses two stereogenic centres, C11 and C12, and both have the R configuration. In the crystal, there are very weak intermolecular C—H⋯Br interactions present (Fig. 2 and Table 1).
Synthesis and crystallization
The title compound was synthesized from 1-bromo-4-[(1E,3Z)-4-bromo-4-nitrobuta-1,3-dienyl]benzene and 7-bromonaphthalen-2-ol (Jarava-Barrera et al., 2013; Pan et al., 2013). To a solution of the chiral amine catalyst 3-(benzylamino)-4-({R-(6-methoxyquinolin-4-yl)[(1S,2R,4S,5R)-5-vinylquinuclidin-2-yl]methyl}amino)cyclobut-3-ene-1,2-dione (5.08 mg, 5 mol%) and 1-bromo-4-[(1E,3Z)-4-bromo-4-nitrobuta-1,3-dienyl]benzene (66.2 mg, 0.2 mmol) in chloroform (6 ml) was added sequentially a solution of 7-bromonaphthalen-2-ol (88.8 mg, 0. 4 mmol) and potassium carbonate (27.6 mg, 0.2 mmol) in water (3.0 ml) with vigorous stirring. The reaction was monitored by TLC. After completion of the reaction, the mixture was extracted with DCM (3 × 5 mL), washed with water, dried and concentrated. The residue was purified by flash to give a white solid. Single crystals were obtained by slow evaporation of a solution in ethyl acetate.
Refinement
Crystal data, data collection and structure .
details are summarized in Table 2Structural data
CCDC reference: 1470708
10.1107/S2414314616005150/pk4003sup1.cif
contains datablock I. DOI:Structure factors: contains datablock I. DOI: 10.1107/S2414314616005150/pk4003Isup2.hkl
Supporting information file. DOI: 10.1107/S2414314616005150/pk4003Isup3.cml
The title compound was synthesized from 1-bromo-4-[(1E,3Z)-4-bromo-4-nitrobuta-1,3-dienyl]benzene and 7-bromonaphthalen-2-ol (Jarava-Barrera et al., 2013; Pan et al., 2013). To a solution of the chiral amine catalyst 3-(benzylamino)-4-({R-(6-methoxyquinolin-4-yl)[(1S,2R,4S,5R)-5-vinylquinuclidin-2-yl]methyl}amino)cyclobut-3-ene-1,2-dione (5.08 mg, 5 mol%) and 1-bromo-4-[(1E,3Z)-4-bromo-4-nitrobuta-1,3-dienyl]benzene (66.2 mg, 0.2 mmol) in chloroform (6 ml) was added sequentially a solution of 7-bromonaphthalen-2-ol (88.8 mg, 0. 4 mmol) and potassium carbonate (27.6 mg, 0.2 mmol) in water (3.0 ml) with vigorous stirring. The reaction was monitored by TLC. After completion of the reaction, the mixture was extracted with DCM (3 × 5 mL), washed with water, dried and concentrated. The residue was purified by flash
to give a white solid. Single crystals were obtained by slow evaporation of a solution in ethyl acetate.The title compound has a dihydrobenzofuran skeleton, which is the effective physiologically active component in many medicinal plants(Ohkawa et al. 1997; Snyder et al., 2011). The molecular structure of the title compound is shown in Fig. 1. The five-membered ring involving C9/C10/C11/C12/O1adopts an
and is characterized by torsion angle values of -140.9 (6) and -18.7 (7)° for C13—C12—C11—N1 and C10—C12—C11—O1, respectively. The naphthyl group is nearly perpendicular to the phenyl ring, while the mean plane of the double bond and its attached substituents is almost coplanar with the phenyl ring [dihedral angles of 79.14 (3) and 13.56 (1)°, respectively]. Furthermore, the C12—C10—C9 and C10—C9—O1 bond angles are 109.7 (5)° and 112.0 (5)°, respectively. The nitro group and bromobenzene alkenyl group are mutually trans to one another, on opposite sides of the furan ring. The molecule possesses two stereogenic centres, C11 and C12, and both have the R configuration. In the crystal, there are very weak intermolecular C—H···Br interactions present (Fig. 2 and Table 1).Data collection: SMART (Bruker, 2013); cell
SAINT (Bruker, 2013); data reduction: SAINT (Bruker, 2013); program(s) used to solve structure: SHELXTL (Sheldrick, 2008); program(s) used to refine structure: SHELXL2013 (Sheldrick, 2015); molecular graphics: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXTL (Sheldrick, 2008).Fig. 1. The structure of the title compound. Displacement ellipsoids are drawn at the 30% probability level. | |
Fig. 2. The crystal packing of the title compound viewed down the crystallographic a axis. C—H···Br interactions are shown with dashed lines. |
C20H13Br2NO3 | F(000) = 468 |
Mr = 475.13 | Dx = 1.704 Mg m−3 |
Monoclinic, P21 | Mo Kα radiation, λ = 0.71073 Å |
a = 9.4796 (15) Å | Cell parameters from 1587 reflections |
b = 7.1550 (12) Å | θ = 4.3–42.0° |
c = 13.651 (2) Å | µ = 4.40 mm−1 |
β = 90.968 (4)° | T = 293 K |
V = 925.8 (3) Å3 | Prismatic, colorless |
Z = 2 | 0.20 × 0.14 × 0.10 mm |
CCD area detector diffractometer | 2731 reflections with I > 2σ(I) |
φ and ω scans | Rint = 0.032 |
Absorption correction: multi-scan (SADABS; Krause et al., 2015) | θmax = 25.5°, θmin = 2.2° |
Tmin = 0.308, Tmax = 0.746 | h = −11→10 |
5364 measured reflections | k = −8→8 |
3269 independent reflections | l = −16→14 |
Refinement on F2 | Hydrogen site location: inferred from neighbouring sites |
Least-squares matrix: full | H-atom parameters constrained |
R[F2 > 2σ(F2)] = 0.041 | w = 1/[σ2(Fo2) + (0.0287P)2] where P = (Fo2 + 2Fc2)/3 |
wR(F2) = 0.093 | (Δ/σ)max < 0.001 |
S = 0.97 | Δρmax = 0.46 e Å−3 |
3269 reflections | Δρmin = −0.33 e Å−3 |
235 parameters | Absolute structure: Flack x determined using 998 quotients [(I+)-(I-)]/[(I+)+(I-)] (Parsons et al., 2013) |
1 restraint | Absolute structure parameter: 0.020 (14) |
C20H13Br2NO3 | V = 925.8 (3) Å3 |
Mr = 475.13 | Z = 2 |
Monoclinic, P21 | Mo Kα radiation |
a = 9.4796 (15) Å | µ = 4.40 mm−1 |
b = 7.1550 (12) Å | T = 293 K |
c = 13.651 (2) Å | 0.20 × 0.14 × 0.10 mm |
β = 90.968 (4)° |
CCD area detector diffractometer | 3269 independent reflections |
Absorption correction: multi-scan (SADABS; Krause et al., 2015) | 2731 reflections with I > 2σ(I) |
Tmin = 0.308, Tmax = 0.746 | Rint = 0.032 |
5364 measured reflections |
R[F2 > 2σ(F2)] = 0.041 | H-atom parameters constrained |
wR(F2) = 0.093 | Δρmax = 0.46 e Å−3 |
S = 0.97 | Δρmin = −0.33 e Å−3 |
3269 reflections | Absolute structure: Flack x determined using 998 quotients [(I+)-(I-)]/[(I+)+(I-)] (Parsons et al., 2013) |
235 parameters | Absolute structure parameter: 0.020 (14) |
1 restraint |
Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. |
x | y | z | Uiso*/Ueq | ||
Br1 | 0.34554 (7) | 0.79114 (10) | 0.40480 (6) | 0.0566 (2) | |
Br2 | 0.15172 (9) | 0.04620 (14) | 0.97004 (6) | 0.0734 (3) | |
N1 | 0.8641 (6) | 1.1062 (9) | 0.8084 (5) | 0.0505 (17) | |
O1 | 0.9655 (4) | 0.8187 (7) | 0.7633 (4) | 0.0494 (13) | |
O2 | 0.7964 (6) | 1.1871 (10) | 0.8702 (5) | 0.087 (2) | |
O3 | 0.9374 (6) | 1.1853 (8) | 0.7504 (5) | 0.0684 (16) | |
C1 | 0.7710 (8) | 0.6837 (11) | 0.3851 (6) | 0.055 (2) | |
H1 | 0.8322 | 0.6469 | 0.3362 | 0.066* | |
C2 | 0.6321 (8) | 0.7072 (11) | 0.3625 (6) | 0.0526 (19) | |
H2 | 0.5983 | 0.6878 | 0.2990 | 0.063* | |
C3 | 0.5398 (7) | 0.7617 (10) | 0.4377 (5) | 0.0443 (16) | |
C4 | 0.5847 (6) | 0.7928 (11) | 0.5314 (5) | 0.0393 (14) | |
H4 | 0.5215 | 0.8284 | 0.5793 | 0.047* | |
C5 | 0.7298 (6) | 0.7699 (10) | 0.5543 (5) | 0.0377 (14) | |
C6 | 0.8249 (7) | 0.7137 (10) | 0.4806 (5) | 0.0428 (16) | |
C7 | 0.9695 (8) | 0.6893 (11) | 0.5051 (6) | 0.053 (2) | |
H7 | 1.0307 | 0.6499 | 0.4567 | 0.064* | |
C8 | 1.0220 (7) | 0.7214 (11) | 0.5972 (6) | 0.0530 (19) | |
H8 | 1.1172 | 0.7060 | 0.6126 | 0.064* | |
C9 | 0.9269 (6) | 0.7780 (11) | 0.6662 (5) | 0.0431 (15) | |
C10 | 0.7863 (6) | 0.8018 (10) | 0.6493 (4) | 0.0364 (13) | |
C11 | 0.8482 (7) | 0.8968 (10) | 0.8071 (5) | 0.0429 (17) | |
H11 | 0.8380 | 0.8485 | 0.8738 | 0.052* | |
C12 | 0.7149 (6) | 0.8505 (9) | 0.7436 (5) | 0.0406 (16) | |
H12 | 0.6551 | 0.9613 | 0.7352 | 0.049* | |
C13 | 0.6332 (7) | 0.6920 (10) | 0.7872 (5) | 0.0393 (15) | |
H13 | 0.6821 | 0.5818 | 0.8000 | 0.047* | |
C14 | 0.4995 (7) | 0.6957 (10) | 0.8085 (5) | 0.0435 (16) | |
H14 | 0.4525 | 0.8081 | 0.7975 | 0.052* | |
C15 | 0.4160 (6) | 0.5434 (11) | 0.8476 (4) | 0.0401 (14) | |
C16 | 0.2702 (6) | 0.5486 (12) | 0.8480 (5) | 0.0486 (16) | |
H16 | 0.2250 | 0.6550 | 0.8241 | 0.058* | |
C17 | 0.1888 (7) | 0.4044 (11) | 0.8820 (6) | 0.0510 (19) | |
H17 | 0.0909 | 0.4115 | 0.8804 | 0.061* | |
C18 | 0.2568 (7) | 0.2504 (11) | 0.9182 (5) | 0.049 (2) | |
C19 | 0.4018 (7) | 0.2356 (10) | 0.9217 (5) | 0.0497 (18) | |
H19 | 0.4455 | 0.1295 | 0.9472 | 0.060* | |
C20 | 0.4800 (7) | 0.3820 (11) | 0.8865 (5) | 0.0457 (17) | |
H20 | 0.5779 | 0.3740 | 0.8886 | 0.055* |
U11 | U22 | U33 | U12 | U13 | U23 | |
Br1 | 0.0575 (4) | 0.0457 (4) | 0.0659 (5) | 0.0035 (4) | −0.0212 (3) | −0.0074 (4) |
Br2 | 0.0799 (6) | 0.0793 (6) | 0.0607 (5) | −0.0367 (5) | −0.0063 (4) | 0.0148 (5) |
N1 | 0.038 (3) | 0.058 (4) | 0.055 (4) | 0.000 (3) | −0.003 (3) | −0.012 (3) |
O1 | 0.041 (2) | 0.058 (4) | 0.049 (3) | 0.013 (2) | −0.011 (2) | −0.012 (3) |
O2 | 0.074 (4) | 0.085 (5) | 0.102 (6) | 0.006 (4) | 0.015 (4) | −0.040 (4) |
O3 | 0.069 (4) | 0.061 (4) | 0.075 (4) | −0.019 (3) | 0.001 (3) | 0.000 (3) |
C1 | 0.064 (5) | 0.062 (5) | 0.041 (5) | −0.001 (4) | 0.018 (4) | −0.009 (4) |
C2 | 0.066 (5) | 0.056 (5) | 0.036 (4) | −0.010 (4) | −0.001 (4) | −0.002 (4) |
C3 | 0.052 (4) | 0.036 (4) | 0.045 (4) | −0.003 (3) | −0.004 (3) | −0.001 (3) |
C4 | 0.042 (3) | 0.033 (3) | 0.043 (4) | −0.001 (4) | −0.001 (3) | −0.003 (4) |
C5 | 0.047 (3) | 0.029 (3) | 0.037 (4) | −0.003 (3) | 0.004 (3) | 0.006 (3) |
C6 | 0.050 (4) | 0.043 (4) | 0.035 (4) | −0.003 (3) | 0.011 (3) | −0.002 (3) |
C7 | 0.052 (4) | 0.054 (5) | 0.054 (5) | 0.004 (4) | 0.014 (4) | −0.013 (4) |
C8 | 0.034 (4) | 0.060 (5) | 0.065 (5) | 0.007 (3) | 0.007 (3) | −0.004 (4) |
C9 | 0.044 (3) | 0.037 (3) | 0.048 (4) | 0.005 (3) | −0.002 (3) | 0.001 (4) |
C10 | 0.042 (3) | 0.030 (3) | 0.038 (4) | −0.001 (3) | 0.004 (3) | 0.001 (3) |
C11 | 0.047 (4) | 0.046 (4) | 0.036 (4) | −0.001 (3) | −0.002 (3) | −0.002 (3) |
C12 | 0.039 (3) | 0.045 (4) | 0.037 (4) | −0.001 (3) | −0.006 (3) | 0.002 (3) |
C13 | 0.047 (4) | 0.039 (4) | 0.032 (4) | 0.001 (3) | −0.003 (3) | 0.001 (3) |
C14 | 0.045 (4) | 0.045 (4) | 0.041 (4) | 0.000 (3) | −0.002 (3) | 0.003 (3) |
C15 | 0.042 (3) | 0.045 (4) | 0.034 (3) | 0.001 (3) | 0.002 (3) | −0.003 (3) |
C16 | 0.041 (4) | 0.050 (4) | 0.055 (4) | 0.004 (4) | 0.002 (3) | −0.003 (4) |
C17 | 0.042 (4) | 0.062 (5) | 0.049 (5) | −0.006 (4) | −0.002 (3) | −0.001 (4) |
C18 | 0.053 (4) | 0.060 (6) | 0.034 (4) | −0.016 (4) | 0.005 (3) | 0.002 (3) |
C19 | 0.060 (4) | 0.049 (5) | 0.040 (4) | −0.003 (3) | −0.006 (3) | 0.008 (3) |
C20 | 0.041 (4) | 0.056 (4) | 0.041 (4) | −0.002 (3) | −0.002 (3) | 0.006 (3) |
Br1—C3 | 1.900 (6) | C8—H8 | 0.9300 |
Br2—C18 | 1.911 (7) | C9—C10 | 1.359 (8) |
N1—O3 | 1.204 (8) | C10—C12 | 1.505 (9) |
N1—O2 | 1.215 (8) | C11—C12 | 1.556 (9) |
N1—C11 | 1.506 (10) | C11—H11 | 0.9800 |
O1—C11 | 1.389 (8) | C12—C13 | 1.501 (9) |
O1—C9 | 1.400 (8) | C12—H12 | 0.9800 |
C1—C2 | 1.358 (10) | C13—C14 | 1.306 (9) |
C1—C6 | 1.408 (11) | C13—H13 | 0.9300 |
C1—H1 | 0.9300 | C14—C15 | 1.454 (10) |
C2—C3 | 1.415 (10) | C14—H14 | 0.9300 |
C2—H2 | 0.9300 | C15—C16 | 1.382 (8) |
C3—C4 | 1.359 (9) | C15—C20 | 1.404 (10) |
C4—C5 | 1.415 (8) | C16—C17 | 1.374 (10) |
C4—H4 | 0.9300 | C16—H16 | 0.9300 |
C5—C10 | 1.413 (9) | C17—C18 | 1.365 (11) |
C5—C6 | 1.421 (9) | C17—H17 | 0.9300 |
C6—C7 | 1.416 (10) | C18—C19 | 1.378 (10) |
C7—C8 | 1.364 (11) | C19—C20 | 1.374 (10) |
C7—H7 | 0.9300 | C19—H19 | 0.9300 |
C8—C9 | 1.376 (9) | C20—H20 | 0.9300 |
O3—N1—O2 | 123.4 (7) | O1—C11—C12 | 108.8 (5) |
O3—N1—C11 | 121.2 (7) | N1—C11—C12 | 107.3 (6) |
O2—N1—C11 | 115.4 (7) | O1—C11—H11 | 110.5 |
C11—O1—C9 | 107.0 (5) | N1—C11—H11 | 110.5 |
C2—C1—C6 | 121.7 (7) | C12—C11—H11 | 110.5 |
C2—C1—H1 | 119.1 | C13—C12—C10 | 114.0 (6) |
C6—C1—H1 | 119.1 | C13—C12—C11 | 111.0 (5) |
C1—C2—C3 | 118.6 (7) | C10—C12—C11 | 98.8 (5) |
C1—C2—H2 | 120.7 | C13—C12—H12 | 110.8 |
C3—C2—H2 | 120.7 | C10—C12—H12 | 110.8 |
C4—C3—C2 | 122.7 (6) | C11—C12—H12 | 110.8 |
C4—C3—Br1 | 119.4 (5) | C14—C13—C12 | 125.6 (7) |
C2—C3—Br1 | 117.9 (5) | C14—C13—H13 | 117.2 |
C3—C4—C5 | 118.5 (6) | C12—C13—H13 | 117.2 |
C3—C4—H4 | 120.8 | C13—C14—C15 | 127.1 (7) |
C5—C4—H4 | 120.8 | C13—C14—H14 | 116.5 |
C10—C5—C4 | 122.4 (6) | C15—C14—H14 | 116.5 |
C10—C5—C6 | 117.4 (6) | C16—C15—C20 | 116.5 (7) |
C4—C5—C6 | 120.1 (6) | C16—C15—C14 | 122.1 (7) |
C1—C6—C7 | 122.3 (6) | C20—C15—C14 | 121.4 (6) |
C1—C6—C5 | 118.3 (6) | C17—C16—C15 | 123.2 (8) |
C7—C6—C5 | 119.4 (6) | C17—C16—H16 | 118.4 |
C8—C7—C6 | 122.3 (6) | C15—C16—H16 | 118.4 |
C8—C7—H7 | 118.9 | C18—C17—C16 | 117.7 (6) |
C6—C7—H7 | 118.9 | C18—C17—H17 | 121.2 |
C7—C8—C9 | 116.6 (6) | C16—C17—H17 | 121.2 |
C7—C8—H8 | 121.7 | C17—C18—C19 | 122.6 (7) |
C9—C8—H8 | 121.7 | C17—C18—Br2 | 120.4 (5) |
C10—C9—C8 | 124.9 (7) | C19—C18—Br2 | 117.0 (6) |
C10—C9—O1 | 112.0 (5) | C20—C19—C18 | 118.2 (7) |
C8—C9—O1 | 123.1 (6) | C20—C19—H19 | 120.9 |
C9—C10—C5 | 119.4 (6) | C18—C19—H19 | 120.9 |
C9—C10—C12 | 109.7 (5) | C19—C20—C15 | 121.8 (6) |
C5—C10—C12 | 130.8 (5) | C19—C20—H20 | 119.1 |
O1—C11—N1 | 109.0 (6) | C15—C20—H20 | 119.1 |
C6—C1—C2—C3 | −0.5 (11) | C9—O1—C11—C12 | 17.4 (7) |
C1—C2—C3—C4 | 0.5 (11) | O3—N1—C11—O1 | 24.1 (9) |
C1—C2—C3—Br1 | −179.4 (6) | O2—N1—C11—O1 | −157.1 (6) |
C2—C3—C4—C5 | 0.1 (11) | O3—N1—C11—C12 | −93.6 (7) |
Br1—C3—C4—C5 | 179.9 (5) | O2—N1—C11—C12 | 85.2 (8) |
C3—C4—C5—C10 | 179.1 (6) | C9—C10—C12—C13 | −104.2 (7) |
C3—C4—C5—C6 | −0.6 (10) | C5—C10—C12—C13 | 72.0 (9) |
C2—C1—C6—C7 | 179.8 (7) | C9—C10—C12—C11 | 13.6 (8) |
C2—C1—C6—C5 | 0.0 (11) | C5—C10—C12—C11 | −170.2 (7) |
C10—C5—C6—C1 | −179.1 (7) | O1—C11—C12—C13 | 101.3 (6) |
C4—C5—C6—C1 | 0.6 (10) | N1—C11—C12—C13 | −140.9 (6) |
C10—C5—C6—C7 | 1.1 (10) | O1—C11—C12—C10 | −18.7 (7) |
C4—C5—C6—C7 | −179.2 (7) | N1—C11—C12—C10 | 99.1 (6) |
C1—C6—C7—C8 | 178.8 (7) | C10—C12—C13—C14 | −123.6 (7) |
C5—C6—C7—C8 | −1.4 (11) | C11—C12—C13—C14 | 125.9 (7) |
C6—C7—C8—C9 | 0.5 (11) | C12—C13—C14—C15 | 177.8 (6) |
C7—C8—C9—C10 | 0.7 (12) | C13—C14—C15—C16 | −165.8 (7) |
C7—C8—C9—O1 | −179.1 (7) | C13—C14—C15—C20 | 13.8 (11) |
C11—O1—C9—C10 | −8.4 (8) | C20—C15—C16—C17 | −1.5 (10) |
C11—O1—C9—C8 | 171.3 (7) | C14—C15—C16—C17 | 178.1 (7) |
C8—C9—C10—C5 | −0.9 (11) | C15—C16—C17—C18 | 1.0 (11) |
O1—C9—C10—C5 | 178.8 (6) | C16—C17—C18—C19 | 0.1 (11) |
C8—C9—C10—C12 | 175.8 (7) | C16—C17—C18—Br2 | 178.4 (5) |
O1—C9—C10—C12 | −4.4 (9) | C17—C18—C19—C20 | −0.5 (11) |
C4—C5—C10—C9 | −179.7 (7) | Br2—C18—C19—C20 | −178.8 (6) |
C6—C5—C10—C9 | 0.0 (10) | C18—C19—C20—C15 | −0.2 (11) |
C4—C5—C10—C12 | 4.4 (12) | C16—C15—C20—C19 | 1.1 (10) |
C6—C5—C10—C12 | −175.9 (7) | C14—C15—C20—C19 | −178.6 (7) |
C9—O1—C11—N1 | −99.4 (6) |
D—H···A | D—H | H···A | D···A | D—H···A |
C12—H12···Br1i | 0.98 | 3.04 | 3.786 (7) | 134 |
C11—H11···Br2ii | 0.98 | 3.04 | 3.942 (7) | 154 |
Symmetry codes: (i) −x+1, y+1/2, −z+1; (ii) −x+1, y+1/2, −z+2. |
D—H···A | D—H | H···A | D···A | D—H···A |
C12—H12···Br1i | 0.98 | 3.04 | 3.786 (7) | 134.2 |
C11—H11···Br2ii | 0.98 | 3.04 | 3.942 (7) | 154.2 |
Symmetry codes: (i) −x+1, y+1/2, −z+1; (ii) −x+1, y+1/2, −z+2. |
Experimental details
Crystal data | |
Chemical formula | C20H13Br2NO3 |
Mr | 475.13 |
Crystal system, space group | Monoclinic, P21 |
Temperature (K) | 293 |
a, b, c (Å) | 9.4796 (15), 7.1550 (12), 13.651 (2) |
β (°) | 90.968 (4) |
V (Å3) | 925.8 (3) |
Z | 2 |
Radiation type | Mo Kα |
µ (mm−1) | 4.40 |
Crystal size (mm) | 0.20 × 0.14 × 0.10 |
Data collection | |
Diffractometer | CCD area detector |
Absorption correction | Multi-scan (SADABS; Krause et al., 2015) |
Tmin, Tmax | 0.308, 0.746 |
No. of measured, independent and observed [I > 2σ(I)] reflections | 5364, 3269, 2731 |
Rint | 0.032 |
(sin θ/λ)max (Å−1) | 0.606 |
Refinement | |
R[F2 > 2σ(F2)], wR(F2), S | 0.041, 0.093, 0.97 |
No. of reflections | 3269 |
No. of parameters | 235 |
No. of restraints | 1 |
H-atom treatment | H-atom parameters constrained |
Δρmax, Δρmin (e Å−3) | 0.46, −0.33 |
Absolute structure | Flack x determined using 998 quotients [(I+)-(I-)]/[(I+)+(I-)] (Parsons et al., 2013) |
Absolute structure parameter | 0.020 (14) |
Computer programs: SMART (Bruker, 2013), SAINT (Bruker, 2013), SHELXTL (Sheldrick, 2008), SHELXL2013 (Sheldrick, 2015).
Acknowledgements
We acknowledge the help of Professor Jie Sun of Shanghai Institute of Organic Chemistry.
References
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The title compound, which was readily synthesized from 1-bromo-4-((1E,3Z)-4-bromo-4-nitrobuta-1,3-dienyl) benzene and 7-bromonaphthalen-2-ol, has the dihydrobenzofuran skeleton, which is the effective physiologically active component in many medicinal plants. The molecular structure of the title compound is shown in Fig. 1. The five-membered ring involving C9/C10/C11/C12/O1 is characterized by torsion angle values of -140.93 (1)° and -18.75 (4)° for C13-C12-C11-N1 and C10-C12-C11-O1. The naphthyl group is nearly perpendicular to the phenyl ring, while the mean plane of the double bond is almost coplanar with the phenyl ring [dihedral angles of 79.14 (3)° and 13.56 (1)°, respectively]. Furthermore, the C12-C10-C9 and C10-C9-O1 bond angles are 109.73 (1)° and 111.99 (2)°, respectively. The molecule possesses two stereogenic centres, C11 and C12, and both have the R configuration. The nitro group and bromobenzene alkenyl group are mutually trans to one another, on opposite sides of the furan ring. In the crystal, there are weak intermolecular C—H···Br interactions.