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Acta Cryst. (2009). E65, o1286    [ doi:10.1107/S1600536809017085 ]

Darifenacin hydrobromide

S. Selvanayagam, B. Sridhar and K. Ravikumar

Abstract top

In the title compound {systematic name: (S)-3-[(aminocarbonyl)diphenylmethyl]-1-[2-(2,3-dihydrobenzofuran-5-yl)ethyl]pyrrolidinium bromide}, C28H31N2O2+·Br-, the pyrrolidine rings adopts an envelope conformation. The two phenyl rings make a dihedral angle of 72.5 (1)°. The four coplanar atoms of the pyrrolidine ring makes dihedral angles of 33.1 (2) and 82.8 (2)° with the two phenyl rings. The molecular conformation is influenced by a C-H...O interaction. In the crystal packing, there are two N-H...Br hydrogen bonds running in opposite directions. They appear to form C(10) and C(9) chain motifs in the unit cell. In addition, the molecular packing is further stabilized by C-H...Br and C-H...O hydrogen bonds. The C atom bonded to the benzofuran ring system is disordered in a 0.66:0.34 ratio.

Comment top

Darifenacin is a selective muscarinic M3-receptor antagonist that has been evaluated in clinical trials in patients with overative bladder syndrome using a controlled-release formulation (Chapple, 2004; Croom & Keating, 2004; Haab et al., 2004; Levin et al., 2008). As no crystal structure of the title compound has yet been published, we have undertaken the single-crystal X-ray diffraction study and report here its results.

The X-ray study confirmed the molecular structure and atomic connectivity for (I), as illustrated in Fig. 1. The bond length of C12—O1 [1.222 (5) Å] confirms the double bond character for amide group, as evidenced by Allen et al. (1987). The C—N and C—-O bond lengths in the pyrrolidine and furan rings are comparable to the related literature values (Selvanayagam et al., 2005).

The pyrrolidine ring adopts an envelope conformation with puckering parameters q2 = 0.213 (4) Å and φ = 34.9 (4)° (Cremer & Pople, 1975). Atom C1 deviates by 0.332 (4) Å from the least-squares plane through the remaining four atoms C1—C4 of the ring. The five membered furan ring in the benzofuran system also adopts an envelope conformation with puckering parameters q2 = 0.162 (7) Å and φ = 85.9 (8)°. Atom C26 deviate -0.232 (7) Å from the least-squares plane through the remaining four atoms (C24/O2/C25/C27) of the ring.

The dihedral angle between the fused benzene and furan rings of the benzofuran system is 4.6 (2)°. The best plane of the pyrrolidine ring and benzofuran system make a dihedral angle of 44.5 (2)°. Two phenyl rings (A and B) are oriented with a dihedral angle of 72.5 (2)°. These two phenyl rings make a dihedral angle of 33.1 (2) and 82.8 (2)°, respectively with pyrroldine ring.

An intramolecular C—H···O interaction is observed in (I) (Table 2). In the crystal packing, the H1 and H2NB atoms bonded to N1 and N2 forms a strong N—H···Br hydrogen bonds which leads a C(10) and C(9) chain motif in the unit cell running in the opposite directions (Fig. 2). In addition to this the molecular packing is further stabilized by strong C—H···Br hydrogen bonds and C—H···O interactions (Table 2).

Related literature top

For general background to darifenacin derivatives, see: Chapple (2004); Croom & Keating (2004); Haab et al. (2004); Levin et al. (2008). For bond-length data, see: Allen et al. (1987); Selvanayagam et al. (2005). For puckering parameters, see: Cremer & Pople (1975).

Experimental top

In order to obtain crystals suitable for X-ray study, darifenacin hydrobromide was dissolved in a methanol-water solution (80:20v/v); the solvents were then allowed to evaporate slowly.

Refinement top

Atoms H2NA and H2NB were located from a difference Fourier map; the remaining H atoms were positioned geometrically and were treated as riding on their parent C and N atoms with C—H distances of 0.93–0.97 Å, N—H distance of 0.91 Å and with Uiso= 1.2Ueq (C or N) for other H. Atom C20 was found to be disordered over two positions. The occupancies were kept fixed at 0.34 and 0.66 during the last cycles of refinement.

Computing details top

Data collection: SMART (Bruker, 2001); cell refinement: SAINT (Bruker, 2001); data reduction: SAINT (Bruker, 2001); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 (Farrugia, 1997) and PLATON (Spek, 2009); software used to prepare material for publication: SHELXL97 (Sheldrick, 2008) and PARST (Nardelli, 1995).

Figures top
[Figure 1] Fig. 1. The structure and atom-numbering scheme for (I); displacement ellipsoids are drawn at the 30% probability level.
[Figure 2] Fig. 2. Molecular packing of (I) viewed down the b axis; H-bonds are shown as dashed lines. For the sake of clarity, H atoms, not involved in hydrogen bonds, have been omitted.
(S)-3-[(aminocarbonyl)diphenylmethyl]-1-[2-(2,3-dihydrobenzofuran-5- yl)ethyl]pyrrolidinium bromide top
Crystal data top
C28H31N2O2+·Br–F000 = 1056
Mr = 507.46Dx = 1.379 Mg m−3
Orthorhombic, P212121Mo Kα radiation
λ = 0.71073 Å
Hall symbol: P 2ac 2abCell parameters from 18484 reflections
a = 10.2632 (7) Åθ = 2.1–24.9º
b = 10.9525 (8) ŵ = 1.71 mm−1
c = 21.7459 (16) ÅT = 293 K
V = 2444.4 (3) Å3Block, colourless
Z = 40.24 × 0.22 × 0.20 mm
Data collection top
Bruker SMART APEX CCD area-detector
diffractometer		4703 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tubeRint = 0.065
Monochromator: graphiteθmax = 28.0º
T = 293 Kθmin = 1.9º
ω scansh = −13→13
Absorption correction: nonek = −14→14
27916 measured reflectionsl = −28→28
5777 independent reflections
Refinement top
Refinement on F2Hydrogen site location: inferred from neighbouring sites
Least-squares matrix: fullH atoms treated by a mixture of
independent and constrained refinement
R[F2 > 2σ(F2)] = 0.054  w = 1/[σ2(Fo2) + (0.030P)2 + 2.3972P]
where P = (Fo2 + 2Fc2)/3
wR(F2) = 0.121(Δ/σ)max < 0.001
S = 1.07Δρmax = 0.55 e Å−3
5777 reflectionsΔρmin = −0.84 e Å−3
315 parametersExtinction correction: none
2 restraintsAbsolute structure: Flack (1983), 2471 Friedel pairs
Primary atom site location: structure-invariant direct methodsFlack parameter: 0.005 (13)
Secondary atom site location: difference Fourier map
Crystal data top
C28H31N2O2+·Br–V = 2444.4 (3) Å3
Mr = 507.46Z = 4
Orthorhombic, P212121Mo Kα
a = 10.2632 (7) ŵ = 1.71 mm−1
b = 10.9525 (8) ÅT = 293 K
c = 21.7459 (16) Å0.24 × 0.22 × 0.20 mm
Data collection top
Bruker SMART APEX CCD area-detector
diffractometer		5777 independent reflections
Absorption correction: none4703 reflections with I > 2σ(I)
27916 measured reflectionsRint = 0.065
Refinement top
R[F2 > 2σ(F2)] = 0.054H atoms treated by a mixture of
independent and constrained refinement
wR(F2) = 0.121Δρmax = 0.55 e Å−3
S = 1.07Δρmin = −0.84 e Å−3
5777 reflectionsAbsolute structure: Flack (1983), 2471 Friedel pairs
315 parametersFlack parameter: 0.005 (13)
2 restraints
Special details top

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
xyzUiso*/UeqOcc. (<1)
Br10.20755 (4)0.88262 (6)0.09168 (2)0.07287 (18)
O10.8147 (3)0.9481 (3)1.04271 (14)0.0553 (8)
O20.2700 (4)0.7835 (4)0.66039 (17)0.0893 (13)
N10.4854 (5)0.8538 (3)1.00332 (19)0.0796 (14)
H10.40340.85871.01900.096*
N20.9041 (4)1.0090 (4)1.1310 (2)0.0599 (10)
H2NA0.899 (6)1.047 (5)1.1657 (14)0.08 (2)*
H2NB0.979 (3)0.977 (5)1.124 (3)0.088 (19)*
C10.5303 (4)0.9721 (3)1.02376 (18)0.0430 (9)
H1A0.46341.03341.01750.052*
H1B0.60790.99631.00140.052*
C20.5605 (3)0.9574 (3)1.0923 (2)0.0389 (8)
H20.48090.97921.11460.047*
C30.5793 (4)0.8189 (4)1.1003 (2)0.0475 (9)
H3A0.67060.79991.10680.057*
H3B0.52990.78971.13540.057*
C40.5312 (6)0.7607 (4)1.0422 (2)0.0686 (14)
H4A0.60140.71631.02240.082*
H4B0.46150.70371.05140.082*
C50.6692 (3)1.0458 (3)1.11486 (17)0.0362 (8)
C60.6657 (3)1.0607 (4)1.18514 (18)0.0426 (9)
C70.6340 (5)0.9655 (5)1.2246 (2)0.0617 (12)
H70.61430.88901.20850.074*
C80.6316 (6)0.9834 (6)1.2875 (2)0.0774 (16)
H80.60840.91901.31310.093*
C90.6623 (6)1.0930 (6)1.3127 (2)0.0794 (17)
H90.66071.10411.35510.095*
C100.6950 (7)1.1847 (6)1.2750 (2)0.0826 (17)
H100.71691.25971.29210.099*
C110.6975 (5)1.1726 (4)1.2122 (2)0.0611 (11)
H110.72021.23881.18770.073*
C120.8038 (4)0.9953 (3)1.0934 (2)0.0411 (8)
C130.6455 (3)1.1693 (3)1.08343 (16)0.0351 (7)
C140.7313 (4)1.2233 (4)1.04213 (18)0.0448 (9)
H140.81161.18681.03460.054*
C150.6995 (5)1.3297 (4)1.0122 (2)0.0540 (10)
H150.75761.36260.98380.065*
C160.5835 (4)1.3883 (4)1.0233 (2)0.0539 (10)
H160.56311.46111.00340.065*
C170.4976 (4)1.3360 (4)1.06486 (19)0.0516 (10)
H170.41811.37381.07270.062*
C180.5280 (4)1.2300 (4)1.0944 (2)0.0476 (9)
H180.46931.19741.12250.057*
C190.4492 (5)0.8315 (4)0.94064 (19)0.0540 (10)
H19A0.35830.80720.94120.065*
H19B0.49830.76060.92740.065*
C20A0.4620 (17)0.9225 (13)0.8917 (6)0.061 (4)0.34
H20A0.55070.92340.87620.073*0.34
H20B0.44171.00310.90750.073*0.34
C20B0.3745 (7)0.9232 (6)0.9058 (3)0.0522 (15)0.66
H20C0.41751.00190.90900.063*0.66
H20D0.28820.93100.92350.063*0.66
C210.3624 (6)0.8874 (5)0.8370 (2)0.0757 (15)
C220.2571 (6)0.9394 (5)0.8092 (3)0.0838 (19)
H220.20820.99630.83100.101*
C230.2203 (7)0.9105 (5)0.7496 (3)0.0851 (17)
H230.14900.94770.73100.102*
C240.2931 (6)0.8250 (5)0.7192 (2)0.0676 (13)
C250.3778 (7)0.7098 (8)0.6432 (3)0.101 (2)
H25A0.43290.75370.61450.121*
H25B0.34740.63580.62330.121*
C260.4540 (6)0.6781 (7)0.7004 (3)0.0924 (19)
H26A0.54700.68750.69410.111*
H26B0.43570.59560.71420.111*
C270.4011 (5)0.7728 (5)0.7451 (2)0.0620 (12)
C280.4357 (6)0.8019 (5)0.8044 (2)0.0731 (15)
H280.50750.76490.82270.088*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Br10.04001 (18)0.1050 (4)0.0736 (3)−0.0003 (3)−0.0002 (2)0.0401 (3)
O10.0539 (18)0.0521 (17)0.0601 (18)0.0106 (14)0.0124 (14)−0.0081 (14)
O20.105 (3)0.098 (3)0.065 (2)−0.006 (3)−0.041 (2)−0.005 (2)
N10.133 (4)0.044 (2)0.062 (2)−0.029 (2)−0.040 (3)0.0073 (18)
N20.0346 (19)0.075 (3)0.070 (3)0.0114 (19)0.0007 (18)−0.004 (2)
C10.049 (2)0.0344 (19)0.045 (2)−0.0030 (16)−0.0053 (17)−0.0020 (16)
C20.0372 (17)0.0395 (19)0.0400 (19)−0.0023 (15)0.0002 (17)0.0062 (17)
C30.055 (2)0.042 (2)0.046 (2)−0.0027 (18)0.0002 (19)0.0074 (18)
C40.108 (4)0.039 (2)0.058 (3)0.012 (3)−0.013 (3)0.001 (2)
C50.0321 (17)0.0388 (19)0.0378 (19)−0.0017 (14)0.0028 (13)−0.0005 (15)
C60.0356 (18)0.051 (2)0.041 (2)0.0044 (16)−0.0004 (15)0.0007 (17)
C70.087 (3)0.060 (3)0.039 (2)−0.002 (3)0.003 (2)0.001 (2)
C80.113 (4)0.081 (4)0.039 (3)0.012 (3)−0.002 (3)0.009 (3)
C90.095 (4)0.106 (5)0.037 (2)0.033 (3)−0.006 (2)−0.015 (3)
C100.098 (4)0.094 (4)0.056 (3)0.018 (4)−0.023 (3)−0.036 (3)
C110.071 (3)0.060 (3)0.053 (3)−0.006 (3)−0.007 (2)−0.005 (2)
C120.0372 (17)0.0320 (17)0.054 (2)0.0011 (15)0.008 (2)0.0026 (17)
C130.0376 (16)0.0329 (17)0.0347 (18)−0.0025 (13)−0.0019 (14)−0.0049 (15)
C140.039 (2)0.041 (2)0.054 (2)−0.0039 (16)0.0063 (17)−0.0055 (17)
C150.061 (2)0.042 (2)0.059 (2)−0.013 (2)0.003 (2)0.0085 (18)
C160.071 (3)0.038 (2)0.052 (2)0.002 (2)−0.014 (2)−0.003 (2)
C170.059 (2)0.046 (2)0.050 (2)0.0158 (19)−0.0084 (19)−0.0079 (18)
C180.0421 (19)0.055 (2)0.046 (2)0.0082 (17)0.0016 (18)0.000 (2)
C190.070 (3)0.041 (2)0.051 (2)0.002 (2)−0.012 (2)−0.0066 (19)
C20A0.071 (9)0.058 (8)0.053 (8)−0.014 (7)−0.012 (7)0.015 (6)
C20B0.058 (4)0.041 (3)0.058 (4)0.005 (3)−0.009 (4)0.003 (3)
C210.123 (4)0.049 (3)0.055 (3)−0.007 (3)−0.026 (3)0.006 (2)
C220.114 (5)0.067 (3)0.071 (4)0.021 (3)−0.013 (3)0.000 (3)
C230.094 (4)0.071 (4)0.090 (4)0.016 (3)−0.038 (4)−0.009 (3)
C240.077 (3)0.068 (3)0.058 (3)−0.010 (3)−0.026 (3)0.012 (2)
C250.098 (5)0.141 (7)0.063 (4)−0.020 (5)−0.001 (3)−0.021 (4)
C260.079 (4)0.105 (5)0.093 (4)0.002 (3)−0.018 (3)−0.022 (4)
C270.061 (3)0.070 (3)0.055 (3)−0.013 (2)−0.017 (2)0.002 (2)
C280.084 (4)0.066 (3)0.070 (3)0.004 (3)−0.037 (3)0.005 (3)
Geometric parameters (Å, °) top
O1—C121.222 (5)C13—C181.397 (5)
O2—C241.378 (6)C14—C151.374 (6)
O2—C251.420 (8)C14—H140.9300
N1—C41.406 (6)C15—C161.375 (7)
N1—C191.434 (5)C15—H150.9300
N1—C11.446 (5)C16—C171.387 (6)
N1—H10.9100C16—H160.9300
N2—C121.324 (6)C17—C181.363 (6)
N2—H2NA0.863 (10)C17—H170.9300
N2—H2NB0.860 (10)C18—H180.9300
C1—C21.530 (6)C19—C20A1.464 (13)
C1—H1A0.9700C19—C20B1.473 (7)
C1—H1B0.9700C19—H19A0.9700
C2—C31.539 (5)C19—H19B0.9700
C2—C51.557 (5)C20A—C211.614 (14)
C2—H20.9800C20A—H20A0.9700
C3—C41.499 (6)C20A—H20B0.9700
C3—H3A0.9700C20B—C211.551 (9)
C3—H3B0.9700C20B—H20C0.9700
C4—H4A0.9700C20B—H20D0.9700
C4—H4B0.9700C21—C221.363 (8)
C5—C131.535 (5)C21—C281.395 (8)
C5—C61.537 (5)C22—C231.388 (8)
C5—C121.561 (5)C22—H220.9300
C6—C71.389 (6)C23—C241.368 (8)
C6—C111.398 (6)C23—H230.9300
C7—C81.381 (7)C24—C271.368 (7)
C7—H70.9300C25—C261.511 (8)
C8—C91.357 (8)C25—H25A0.9700
C8—H80.9300C25—H25B0.9700
C9—C101.338 (8)C26—C271.522 (8)
C9—H90.9300C26—H26A0.9700
C10—C111.372 (6)C26—H26B0.9700
C10—H100.9300C27—C281.375 (7)
C11—H110.9300C28—H280.9300
C13—C141.390 (5)
C24—O2—C25107.4 (4)C14—C15—C16121.3 (4)
C4—N1—C19122.4 (4)C14—C15—H15119.4
C4—N1—C1111.0 (4)C16—C15—H15119.4
C19—N1—C1121.8 (4)C15—C16—C17118.2 (4)
C4—N1—H197.3C15—C16—H16120.9
C19—N1—H197.3C17—C16—H16120.9
C1—N1—H197.3C18—C17—C16120.9 (4)
C12—N2—H2NA123 (4)C18—C17—H17119.6
C12—N2—H2NB122 (4)C16—C17—H17119.6
H2NA—N2—H2NB114 (6)C17—C18—C13121.5 (4)
N1—C1—C2105.6 (3)C17—C18—H18119.2
N1—C1—H1A110.6C13—C18—H18119.2
C2—C1—H1A110.6N1—C19—C20A123.5 (6)
N1—C1—H1B110.6N1—C19—C20B120.5 (4)
C2—C1—H1B110.6C20A—C19—C20B37.7 (7)
H1A—C1—H1B108.7N1—C19—H19A106.4
C1—C2—C3103.9 (3)C20A—C19—H19A106.4
C1—C2—C5112.8 (3)C20B—C19—H19A72.2
C3—C2—C5119.1 (3)N1—C19—H19B106.4
C1—C2—H2106.8C20A—C19—H19B106.4
C3—C2—H2106.8C20B—C19—H19B131.6
C5—C2—H2106.8H19A—C19—H19B106.5
C4—C3—C2106.4 (4)C19—C20A—C21108.4 (9)
C4—C3—H3A110.5C19—C20A—H20A110.0
C2—C3—H3A110.5C21—C20A—H20A110.0
C4—C3—H3B110.5C19—C20A—H20B110.0
C2—C3—H3B110.5C21—C20A—H20B110.0
H3A—C3—H3B108.6H20A—C20A—H20B108.4
N1—C4—C3108.0 (4)C19—C20B—C21111.4 (5)
N1—C4—H4A110.1C19—C20B—H20C109.3
C3—C4—H4A110.1C21—C20B—H20C109.3
N1—C4—H4B110.1C19—C20B—H20D109.3
C3—C4—H4B110.1C21—C20B—H20D109.3
H4A—C4—H4B108.4H20C—C20B—H20D108.0
C13—C5—C6110.2 (3)C22—C21—C28118.9 (5)
C13—C5—C2107.1 (3)C22—C21—C20B112.6 (6)
C6—C5—C2111.3 (3)C28—C21—C20B128.1 (5)
C13—C5—C12108.6 (3)C22—C21—C20A136.8 (8)
C6—C5—C12110.8 (3)C28—C21—C20A101.1 (8)
C2—C5—C12108.6 (3)C20B—C21—C20A34.8 (6)
C7—C6—C11116.9 (4)C21—C22—C23122.3 (6)
C7—C6—C5122.7 (4)C21—C22—H22118.8
C11—C6—C5120.4 (4)C23—C22—H22118.8
C8—C7—C6120.6 (5)C24—C23—C22117.3 (5)
C8—C7—H7119.7C24—C23—H23121.3
C6—C7—H7119.7C22—C23—H23121.3
C9—C8—C7121.5 (5)C23—C24—C27122.0 (5)
C9—C8—H8119.3C23—C24—O2125.4 (5)
C7—C8—H8119.3C27—C24—O2112.6 (5)
C10—C9—C8118.3 (5)O2—C25—C26108.4 (5)
C10—C9—H9120.8O2—C25—H25A110.0
C8—C9—H9120.8C26—C25—H25A110.0
C9—C10—C11122.8 (5)O2—C25—H25B110.0
C9—C10—H10118.6C26—C25—H25B110.0
C11—C10—H10118.6H25A—C25—H25B108.4
C10—C11—C6120.0 (5)C25—C26—C27100.7 (5)
C10—C11—H11120.0C25—C26—H26A111.6
C6—C11—H11120.0C27—C26—H26A111.6
O1—C12—N2122.4 (4)C25—C26—H26B111.6
O1—C12—C5120.1 (4)C27—C26—H26B111.6
N2—C12—C5117.6 (3)H26A—C26—H26B109.4
C14—C13—C18117.1 (3)C24—C27—C28119.9 (5)
C14—C13—C5124.2 (3)C24—C27—C26108.1 (4)
C18—C13—C5118.7 (3)C28—C27—C26131.7 (5)
C15—C14—C13121.1 (4)C27—C28—C21119.5 (5)
C15—C14—H14119.5C27—C28—H28120.2
C13—C14—H14119.5C21—C28—H28120.2
C4—N1—C1—C2−23.2 (6)C5—C13—C14—C15175.0 (4)
C19—N1—C1—C2−179.2 (5)C13—C14—C15—C161.9 (6)
N1—C1—C2—C320.9 (4)C14—C15—C16—C17−1.2 (6)
N1—C1—C2—C5151.3 (4)C15—C16—C17—C180.7 (6)
C1—C2—C3—C4−12.2 (5)C16—C17—C18—C13−0.8 (6)
C5—C2—C3—C4−138.7 (4)C14—C13—C18—C171.4 (6)
C19—N1—C4—C3171.2 (5)C5—C13—C18—C17−175.7 (4)
C1—N1—C4—C315.3 (7)C4—N1—C19—C20A−149.3 (10)
C2—C3—C4—N1−1.1 (6)C1—N1—C19—C20A4.0 (12)
C1—C2—C5—C1340.3 (4)C4—N1—C19—C20B166.0 (6)
C3—C2—C5—C13162.5 (4)C1—N1—C19—C20B−40.7 (8)
C1—C2—C5—C6160.8 (3)N1—C19—C20A—C21−157.4 (7)
C3—C2—C5—C6−77.0 (5)C20B—C19—C20A—C21−59.4 (9)
C1—C2—C5—C12−76.9 (4)N1—C19—C20B—C21172.5 (5)
C3—C2—C5—C1245.3 (5)C20A—C19—C20B—C2165.9 (11)
C13—C5—C6—C7154.5 (4)C19—C20B—C21—C22156.0 (6)
C2—C5—C6—C735.8 (5)C19—C20B—C21—C28−16.8 (10)
C12—C5—C6—C7−85.2 (5)C19—C20B—C21—C20A−62.4 (10)
C13—C5—C6—C11−26.7 (5)C19—C20A—C21—C22118.0 (10)
C2—C5—C6—C11−145.4 (4)C19—C20A—C21—C28−83.9 (11)
C12—C5—C6—C1193.6 (4)C19—C20A—C21—C20B61.1 (9)
C11—C6—C7—C81.5 (7)C28—C21—C22—C230.0 (9)
C5—C6—C7—C8−179.7 (5)C20B—C21—C22—C23−173.6 (6)
C6—C7—C8—C9−1.3 (9)C20A—C21—C22—C23155.2 (10)
C7—C8—C9—C100.2 (9)C21—C22—C23—C241.0 (10)
C8—C9—C10—C110.6 (10)C22—C23—C24—C27−2.5 (9)
C9—C10—C11—C6−0.4 (9)C22—C23—C24—O2178.9 (6)
C7—C6—C11—C10−0.7 (7)C25—O2—C24—C23171.6 (6)
C5—C6—C11—C10−179.5 (5)C25—O2—C24—C27−7.1 (7)
C13—C5—C12—O1−77.7 (4)C24—O2—C25—C2615.4 (7)
C6—C5—C12—O1161.0 (4)O2—C25—C26—C27−16.7 (7)
C2—C5—C12—O138.5 (5)C23—C24—C27—C283.0 (8)
C13—C5—C12—N2100.3 (4)O2—C24—C27—C28−178.2 (5)
C6—C5—C12—N2−20.9 (5)C23—C24—C27—C26177.2 (6)
C2—C5—C12—N2−143.5 (4)O2—C24—C27—C26−4.0 (6)
C6—C5—C13—C14122.6 (4)C25—C26—C27—C2412.5 (6)
C2—C5—C13—C14−116.2 (4)C25—C26—C27—C28−174.3 (6)
C12—C5—C13—C141.0 (5)C24—C27—C28—C21−1.9 (8)
C6—C5—C13—C18−60.5 (4)C26—C27—C28—C21−174.5 (6)
C2—C5—C13—C1860.8 (4)C22—C21—C28—C270.5 (9)
C12—C5—C13—C18177.9 (3)C20B—C21—C28—C27172.9 (6)
C18—C13—C14—C15−2.0 (6)C20A—C21—C28—C27−162.5 (7)
Hydrogen-bond geometry (Å, °) top
D—H···AD—HH···AD···AD—H···A
N1—H1···Br1i0.912.573.453 (6)164
N2—H2NB···Br1ii0.86 (1)2.66 (1)3.514 (4)175 (5)
C18—H18···O2iii0.932.603.382 (6)142
C19—H19B···Br1iv0.972.693.609 (5)158
C4—H4A···Br1iv0.972.923.770 (5)147
C1—H1B···O10.972.372.959 (5)119
Symmetry codes: (i) x, y, z+1; (ii) x+1, y, z+1; (iii) −x+1/2, −y+2, z+1/2; (iv) x+1/2, −y+3/2, −z+1.
Table 1
Selected geometric parameters (Å) top
O1—C121.222 (5)N1—C41.406 (6)
O2—C241.378 (6)N1—C191.434 (5)
O2—C251.420 (8)N1—C11.446 (5)
Table 2
Hydrogen-bond geometry (Å, °) top
D—H···AD—HH···AD···AD—H···A
N1—H1···Br1i0.912.573.453 (6)164
N2—H2NB···Br1ii0.86 (1)2.66 (1)3.514 (4)175 (5)
C18—H18···O2iii0.932.603.382 (6)142
C19—H19B···Br1iv0.972.693.609 (5)158
C4—H4A···Br1iv0.972.923.770 (5)147
C1—H1B···O10.972.372.959 (5)119
Symmetry codes: (i) x, y, z+1; (ii) x+1, y, z+1; (iii) −x+1/2, −y+2, z+1/2; (iv) x+1/2, −y+3/2, −z+1.
Acknowledgements top

SS thanks the Vice Chancellor and management of Kalasalingam University for their support and encouragement.

references
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