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COMMUNICATIONS
ISSN: 2056-9890

1-[(4-Bromo­phen­yl)(morpholin-4-yl)­meth­yl]naphthalen-2-ol

aSchool of Pharmaceutical Sciences, Nanjing University of Chinese Medicine, Nanjing 210046, People's Republic of China
*Correspondence e-mail: qzhaonucm@gmail.com

(Received 28 January 2012; accepted 3 February 2012; online 24 February 2012)

The title compound, C21H20BrNO2, was obtained via a one-pot synthesis from the reaction of 4-bromo­benzaldehyde, 2-naphthol and morpholine. In the asymmetric unit, there are four mol­ecules with similar structures. The morpholine ring adopts a chair conformation, and the hy­droxy group links with the morpholine via an intra­molecular O—H⋯N hydrogen bond. The bromo­phenyl ring is approximately perpendicular to the mean pane of the naphthalene system at dihedral angles of 76.7 (3), 81.4 (3), 79.7 (3) and 84.5 (3)° in the four independent mol­ecules. Weak C—H⋯O hydrogen bonds are observed in the crystal.

Related literature

For the application of the Betti-type reaction, see: Gardiner & Raston (1997[Gardiner, M. & Raston, C. (1997). Coord. Chem. Rev. 166, 1-34.]); Gutsche & Nam (1998[Gutsche, C. D. & Nam, K. C. (1998). J. Am. Chem. Soc. 110, 6153-6162.]).

[Scheme 1]

Experimental

Crystal data
  • C21H20BrNO2

  • Mr = 398.28

  • Triclinic, [P \overline 1]

  • a = 10.514 (2) Å

  • b = 10.700 (2) Å

  • c = 34.002 (7) Å

  • α = 82.32 (3)°

  • β = 89.43 (3)°

  • γ = 88.67 (3)°

  • V = 3789.8 (13) Å3

  • Z = 8

  • Mo Kα radiation

  • μ = 2.18 mm−1

  • T = 293 K

  • 0.20 × 0.20 × 0.20 mm

Data collection
  • Rigaku Mercury2 (2 × 2 bin mode) diffractometer

  • Absorption correction: multi-scan (CrystalClear; Rigaku, 2005[Rigaku (2005). CrystalClear. Rigaku Corporation, Tokyo, Japan.]) Tmin = 0.822, Tmax = 1.000

  • 26170 measured reflections

  • 13194 independent reflections

  • 5620 reflections with I > 2σ(I)

  • Rint = 0.094

Refinement
  • R[F2 > 2σ(F2)] = 0.083

  • wR(F2) = 0.192

  • S = 1.03

  • 13194 reflections

  • 901 parameters

  • H-atom parameters constrained

  • Δρmax = 0.59 e Å−3

  • Δρmin = −0.58 e Å−3

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A D—H H⋯A DA D—H⋯A
O1—H1A⋯N1 0.82 1.92 2.600 (7) 139
O3—H3B⋯N2 0.82 1.92 2.601 (7) 140
O5—H5A⋯N3 0.82 1.91 2.612 (7) 142
O7—H7B⋯N4 0.82 1.93 2.620 (7) 142
C25—H25A⋯O4i 0.93 2.58 3.473 (10) 162
C46—H46A⋯O6ii 0.93 2.57 3.371 (10) 144
C55—H55A⋯O5 0.93 2.59 3.305 (9) 134
C67—H67A⋯O8iii 0.93 2.41 3.208 (9) 143
Symmetry codes: (i) x, y+1, z; (ii) x, y-1, z; (iii) x+1, y, z.

Data collection: CrystalClear (Rigaku, 2005[Rigaku (2005). CrystalClear. Rigaku Corporation, Tokyo, Japan.]); cell refinement: CrystalClear; data reduction: CrystalClear; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); molecular graphics: SHELXTL (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); software used to prepare material for publication: SHELXTL.

Supporting information


Comment top

The reaction of substituted phenols and aldehydes under controlled conditions has been used to build up supramolecular compounds, the most important ones being calixarenes (Gardiner & Raston, 1997; Gutsche & Nam, 1998). 2-Naphthol reacts with aromatic aldehydes to produce 14-aryl-14H-dibenzo[a,j]xanthenes, which could be used as anti-inflamatory agents. Herein we report the synthesis and crystal structure of the title compound (Fig. 1).

In the title compound, bond lengths and angles have normal values. There are four molecules in the asymmetric unit, all having similar conformations. The morpholine rings adopt chair conformation. The dihedral angles between rings A (C1–C10) and B (C12–C17), and between rings C(C22–C31) and D(C33–C38), and between rings E(C43–C52) and F (C54–C59), and between rings G(C64–C73) and H(C75–C80), are 76.7 (3), 81.4 (3), 79.7 (3) and 84.5 (3)°, respectively. The crystal structure is stabilized by intermolecular C–H···O hydrogen bonds, which link the molecules into a three-dimensional network(Fig. 2). The intramolecular O–H···N hydrogen bonds are also present, Table 1.

Related literature top

For the application of Betti-type reaction, see: Gardiner & Raston (1997); Gutsche & Nam (1998).

Experimental top

4-Bromobenzaldehyde (2.76 g, 0.015 mol) and morpholine (1.305 g, 0.015 mol) was added to 2-naphthol (2.16 g, 0.015 mol) without solvent under nitrogen. The temperature was raised to 120°C in one hour gradually and the mixture was stirred at this temperature for 12 h. The system was treated with 30 ml of ethanol 95% and cooled. The precipitate was filtered and washed with a small amount of ethanol 95%. The title compound was isolated using column chromatography (Petroleum ether: ethyl acetate-5:1). Single crystals suitable for X-ray diffraction analysis were obtained from slow evaporation of a solution of the title compound in ethyl acetate at room temperature.

Refinement top

H atoms were positioned geometrically and refined using a riding model with C—H = 0.93–0.97 Å and O—H = 0.82 Å, Uiso(H) = 1.2Ueq(C) and 1.5Ueq(O).

Computing details top

Data collection: CrystalClear (Rigaku, 2005); cell refinement: CrystalClear (Rigaku, 2005); data reduction: CrystalClear (Rigaku, 2005); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXTL (Sheldrick, 2008).

Figures top
[Figure 1] Fig. 1. Perspective structure of the title compound, showing the atom-numbering scheme. Displacement ellipsoids are drawn at the 30% probability level.
[Figure 2] Fig. 2. The crystal packing of the title compound viewed along thec axis showing the hydrogen bondings network.
1-[(4-Bromophenyl)(morpholin-4-yl)methyl]naphthalen-2-ol top
Crystal data top
C21H20BrNO2Z = 8
Mr = 398.28F(000) = 1632
Triclinic, P1Dx = 1.396 Mg m3
Hall symbol: -P 1Mo Kα radiation, λ = 0.71073 Å
a = 10.514 (2) ÅCell parameters from 13194 reflections
b = 10.700 (2) Åθ = 2.7–25.0°
c = 34.002 (7) ŵ = 2.18 mm1
α = 82.32 (3)°T = 293 K
β = 89.43 (3)°Prism, colorless
γ = 88.67 (3)°0.20 × 0.20 × 0.20 mm
V = 3789.8 (13) Å3
Data collection top
Rigaku Mercury2 (2x2 bin mode)
diffractometer
13194 independent reflections
Radiation source: fine-focus sealed tube5620 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.094
Detector resolution: 13.6612 pixels mm-1θmax = 25.0°, θmin = 3.0°
CCD_Profile_fitting scansh = 1212
Absorption correction: multi-scan
(CrystalClear; Rigaku, 2005)
k = 1212
Tmin = 0.822, Tmax = 1.000l = 4040
26170 measured reflections
Refinement top
Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.083Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.192H-atom parameters constrained
S = 1.03 w = 1/[σ2(Fo2) + (0.0538P)2 + 0.6976P]
where P = (Fo2 + 2Fc2)/3
13194 reflections(Δ/σ)max = 0.004
901 parametersΔρmax = 0.59 e Å3
0 restraintsΔρmin = 0.58 e Å3
Crystal data top
C21H20BrNO2γ = 88.67 (3)°
Mr = 398.28V = 3789.8 (13) Å3
Triclinic, P1Z = 8
a = 10.514 (2) ÅMo Kα radiation
b = 10.700 (2) ŵ = 2.18 mm1
c = 34.002 (7) ÅT = 293 K
α = 82.32 (3)°0.20 × 0.20 × 0.20 mm
β = 89.43 (3)°
Data collection top
Rigaku Mercury2 (2x2 bin mode)
diffractometer
13194 independent reflections
Absorption correction: multi-scan
(CrystalClear; Rigaku, 2005)
5620 reflections with I > 2σ(I)
Tmin = 0.822, Tmax = 1.000Rint = 0.094
26170 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0830 restraints
wR(F2) = 0.192H-atom parameters constrained
S = 1.03Δρmax = 0.59 e Å3
13194 reflectionsΔρmin = 0.58 e Å3
901 parameters
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*/Ueq
Br10.54748 (9)0.74290 (8)1.00437 (3)0.0785 (3)
O10.4085 (5)0.3444 (5)0.83872 (16)0.0707 (16)
H1A0.47750.36790.84560.106*
O20.8290 (5)0.3972 (5)0.79797 (17)0.0687 (15)
N10.5990 (5)0.4965 (5)0.82932 (16)0.0439 (15)
C180.6225 (7)0.4945 (7)0.7866 (2)0.052 (2)
H18A0.65990.57330.77520.062*
H18B0.54240.48630.77340.062*
C10.3726 (7)0.5702 (7)0.8216 (2)0.0446 (18)
C120.5094 (7)0.6366 (7)0.8765 (2)0.0492 (19)
C20.3359 (8)0.4461 (8)0.8242 (2)0.059 (2)
C110.5067 (6)0.6007 (6)0.83451 (19)0.0444 (18)
H11A0.53400.67480.81650.053*
C30.2137 (8)0.4159 (9)0.8112 (2)0.065 (2)
H3A0.18920.33240.81310.079*
C150.5245 (7)0.7010 (7)0.9520 (2)0.054 (2)
C210.7237 (6)0.5071 (7)0.8481 (2)0.052 (2)
H21A0.71250.50400.87650.063*
H21B0.76070.58740.83800.063*
C130.5755 (7)0.7402 (7)0.8840 (2)0.061 (2)
H13A0.61540.78900.86290.074*
C170.4468 (7)0.5657 (7)0.9079 (2)0.062 (2)
H17A0.39920.49680.90360.075*
C160.4564 (8)0.5992 (8)0.9458 (2)0.069 (2)
H16A0.41600.55180.96700.082*
C200.8108 (7)0.4022 (8)0.8394 (2)0.068 (2)
H20A0.89270.41190.85140.082*
H20B0.77650.32280.85160.082*
C190.7104 (7)0.3866 (7)0.7802 (2)0.060 (2)
H19A0.67220.30790.79130.072*
H19B0.72240.38510.75190.072*
C140.5849 (8)0.7745 (7)0.9214 (3)0.065 (2)
H14A0.63030.84480.92580.078*
C100.2870 (8)0.6678 (8)0.8067 (2)0.052 (2)
C50.1623 (8)0.6384 (11)0.7935 (2)0.067 (2)
C90.3147 (8)0.7970 (8)0.8055 (2)0.067 (2)
H9A0.39220.82000.81500.081*
C40.1348 (8)0.5093 (12)0.7964 (3)0.081 (3)
H4A0.05620.48770.78740.097*
C80.2272 (11)0.8900 (9)0.7902 (3)0.090 (3)
H8A0.24810.97440.78900.108*
C60.0802 (9)0.7374 (12)0.7783 (3)0.087 (3)
H6A0.00140.71790.76880.105*
C70.1099 (11)0.8595 (13)0.7767 (3)0.103 (4)
H7A0.05220.92270.76660.123*
Br20.74914 (8)0.46258 (9)0.49468 (3)0.0850 (3)
O30.2734 (5)0.5256 (5)0.66728 (16)0.0720 (16)
H3B0.30070.45950.66030.108*
O40.3368 (6)0.0926 (5)0.7095 (2)0.0871 (18)
N20.4301 (5)0.3323 (5)0.67417 (17)0.0502 (16)
C220.4977 (7)0.5507 (6)0.67801 (19)0.0404 (18)
C320.5342 (6)0.4245 (6)0.6655 (2)0.0438 (18)
H32A0.60560.39140.68240.053*
C310.5940 (8)0.6321 (7)0.6884 (2)0.0478 (19)
C360.6813 (8)0.4581 (8)0.5472 (2)0.059 (2)
C330.5839 (7)0.4356 (6)0.6230 (2)0.0449 (18)
C380.5213 (7)0.5069 (8)0.5921 (2)0.068 (2)
H38A0.44550.54870.59710.081*
C400.3465 (9)0.1249 (7)0.6680 (3)0.085 (3)
H40A0.26640.16270.65800.101*
H40B0.36160.04880.65590.101*
C250.4293 (10)0.7827 (8)0.7022 (2)0.067 (2)
H25A0.40520.85920.71060.081*
C260.5586 (9)0.7492 (8)0.7015 (2)0.057 (2)
C390.4515 (7)0.2154 (7)0.6559 (2)0.064 (2)
H39A0.53270.17670.66450.077*
H39B0.45380.23540.62730.077*
C370.5690 (8)0.5175 (8)0.5539 (2)0.072 (2)
H37A0.52520.56450.53310.086*
C300.7248 (8)0.6018 (7)0.6862 (2)0.056 (2)
H30A0.75050.52780.67660.067*
C340.6971 (7)0.3777 (7)0.6150 (3)0.066 (2)
H34A0.74270.33270.63580.079*
C420.4178 (7)0.2967 (7)0.7178 (2)0.065 (2)
H42A0.39790.37130.73020.078*
H42B0.49780.26070.72840.078*
C290.8157 (8)0.6801 (9)0.6980 (2)0.071 (2)
H29A0.90130.65670.69710.085*
C270.6555 (11)0.8284 (8)0.7124 (2)0.073 (3)
H27A0.63300.90550.72050.087*
C230.3719 (8)0.5925 (7)0.6785 (2)0.055 (2)
C240.3385 (9)0.7081 (8)0.6913 (2)0.068 (2)
H24A0.25340.73330.69230.082*
C410.3144 (8)0.2023 (7)0.7271 (2)0.073 (3)
H41A0.30800.17990.75560.088*
H41B0.23380.24060.71780.088*
C280.7798 (11)0.7937 (9)0.7111 (2)0.078 (3)
H28A0.84150.84580.71910.094*
C350.7455 (7)0.3843 (8)0.5767 (3)0.065 (2)
H35A0.81930.34000.57130.078*
Br40.08240 (10)0.62411 (8)0.04967 (3)0.0908 (4)
O70.0940 (5)0.0686 (4)0.03561 (15)0.0605 (14)
H7B0.02530.03360.03900.091*
O80.3346 (5)0.1270 (6)0.07228 (16)0.0684 (15)
N40.0974 (5)0.0084 (5)0.07986 (16)0.0445 (15)
C750.0118 (7)0.1946 (7)0.0873 (2)0.0496 (19)
C740.0022 (6)0.0562 (6)0.10232 (19)0.0403 (18)
H74A0.03080.04940.13000.048*
C760.0422 (7)0.2842 (7)0.1083 (3)0.067 (2)
H76A0.09190.25840.13060.081*
C730.2143 (7)0.0146 (6)0.1338 (2)0.0459 (19)
C650.1669 (7)0.0678 (6)0.0680 (2)0.0464 (19)
C690.4202 (8)0.0709 (7)0.1640 (3)0.072 (3)
H69A0.50090.10730.16230.087*
C640.1265 (7)0.0126 (6)0.1016 (2)0.0445 (19)
C810.2165 (7)0.0648 (7)0.0718 (2)0.061 (2)
H81A0.19880.14430.05570.073*
H81B0.25430.08290.09660.073*
C780.0500 (8)0.4470 (7)0.0644 (3)0.063 (2)
C790.1017 (7)0.3617 (7)0.0423 (2)0.067 (2)
H79A0.14940.38890.01970.080*
C800.0834 (7)0.2355 (7)0.0534 (2)0.065 (2)
H80A0.11880.17690.03840.078*
C670.3703 (8)0.1266 (7)0.0971 (3)0.065 (2)
H67A0.45020.16470.09550.078*
C660.2890 (7)0.1238 (6)0.0670 (2)0.054 (2)
H66A0.31400.16000.04470.065*
C680.3353 (7)0.0718 (6)0.1316 (3)0.050 (2)
C830.2223 (8)0.1999 (7)0.0798 (2)0.063 (2)
H83A0.18480.21720.05480.075*
H83B0.24240.27990.09530.075*
C840.1271 (7)0.1319 (7)0.1022 (2)0.063 (2)
H84A0.16210.12010.12800.076*
H84B0.04970.18280.10630.076*
C720.1825 (7)0.0405 (7)0.1682 (2)0.056 (2)
H72A0.10270.07860.17020.068*
C770.0241 (8)0.4116 (8)0.0971 (3)0.068 (2)
H77A0.06130.47150.11130.082*
C700.3881 (9)0.0193 (8)0.1972 (3)0.075 (3)
H70A0.44390.02180.21830.091*
C710.2653 (9)0.0389 (8)0.1982 (2)0.071 (2)
H71A0.24160.07710.22020.085*
C820.3074 (7)0.0082 (8)0.0506 (2)0.063 (2)
H82A0.38610.04050.04590.076*
H82B0.27140.02070.02500.076*
Br30.65346 (8)0.92999 (11)0.45458 (3)0.1049 (4)
O50.0484 (4)0.9132 (5)0.46306 (15)0.0584 (14)
H5A0.01360.98160.45950.088*
O60.1023 (6)1.3581 (5)0.42469 (16)0.0695 (15)
N30.0234 (5)1.1195 (5)0.41944 (16)0.0446 (15)
C520.0401 (6)0.8411 (7)0.3638 (2)0.0454 (19)
C540.2342 (7)1.0095 (7)0.4130 (2)0.0499 (19)
C440.0357 (6)0.8559 (7)0.4299 (3)0.051 (2)
C470.0175 (7)0.7214 (7)0.3659 (3)0.055 (2)
C450.0902 (7)0.7381 (8)0.4316 (3)0.065 (2)
H45A0.13120.70340.45480.078*
C610.1706 (7)1.2501 (8)0.4179 (2)0.066 (2)
H61A0.24551.27670.40230.080*
H61B0.19861.20580.44310.080*
C510.1093 (7)0.8830 (7)0.3283 (2)0.060 (2)
H51A0.15180.95880.32660.072*
C590.3337 (7)1.0740 (7)0.3931 (2)0.062 (2)
H59A0.31751.13130.37050.075*
C630.0943 (7)1.2306 (7)0.4270 (2)0.060 (2)
H63A0.12531.27470.40210.072*
H63B0.16711.20420.44360.072*
C530.1006 (6)1.0318 (6)0.3973 (2)0.0447 (18)
H53A0.10741.07150.36970.054*
C550.2616 (7)0.9222 (7)0.4462 (2)0.062 (2)
H55A0.19590.87930.46020.075*
C430.0316 (6)0.9085 (6)0.3972 (2)0.0431 (18)
C560.3859 (8)0.8993 (7)0.4584 (2)0.067 (2)
H56A0.40330.84010.48040.080*
C460.0846 (7)0.6732 (8)0.4002 (3)0.072 (3)
H46A0.12520.59650.40130.086*
C500.1154 (8)0.8161 (8)0.2969 (3)0.071 (2)
H50A0.16070.84750.27430.085*
C480.0106 (7)0.6550 (7)0.3323 (3)0.070 (3)
H48A0.05120.57830.33340.085*
C600.0906 (7)1.1613 (7)0.3964 (2)0.060 (2)
H60A0.14001.08870.39240.073*
H60B0.06571.20370.37050.073*
C620.0072 (8)1.3189 (7)0.4476 (2)0.063 (2)
H62A0.01911.27590.47320.076*
H62B0.05421.39260.45220.076*
C580.4572 (8)1.0534 (9)0.4067 (3)0.072 (3)
H58A0.52271.10100.39420.087*
C570.4839 (7)0.9628 (8)0.4385 (3)0.065 (2)
C490.0547 (8)0.7013 (9)0.2983 (3)0.080 (3)
H49A0.05800.65660.27660.096*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Br10.1015 (8)0.0790 (7)0.0584 (6)0.0112 (5)0.0019 (5)0.0239 (5)
O10.057 (4)0.044 (3)0.110 (5)0.004 (3)0.003 (3)0.007 (3)
O20.048 (4)0.093 (4)0.066 (4)0.003 (3)0.010 (3)0.016 (3)
N10.038 (4)0.050 (4)0.045 (4)0.002 (3)0.001 (3)0.009 (3)
C180.054 (5)0.061 (5)0.043 (5)0.011 (4)0.001 (4)0.011 (4)
C10.041 (5)0.046 (5)0.046 (5)0.001 (4)0.008 (4)0.004 (4)
C120.052 (5)0.054 (5)0.040 (5)0.007 (4)0.001 (4)0.002 (4)
C20.055 (6)0.061 (6)0.062 (6)0.010 (5)0.009 (4)0.017 (5)
C110.045 (5)0.049 (5)0.036 (5)0.000 (4)0.004 (4)0.007 (4)
C30.042 (6)0.082 (7)0.075 (6)0.012 (5)0.003 (5)0.021 (5)
C150.064 (6)0.044 (5)0.057 (6)0.012 (4)0.009 (4)0.023 (4)
C210.045 (5)0.060 (5)0.054 (5)0.003 (4)0.002 (4)0.014 (4)
C130.080 (6)0.052 (5)0.050 (6)0.018 (5)0.006 (5)0.003 (4)
C170.076 (6)0.056 (5)0.056 (6)0.016 (4)0.011 (5)0.010 (5)
C160.087 (6)0.078 (6)0.040 (5)0.027 (5)0.020 (4)0.001 (5)
C200.050 (5)0.091 (7)0.065 (6)0.002 (5)0.004 (4)0.012 (5)
C190.059 (6)0.072 (6)0.053 (5)0.002 (5)0.008 (4)0.020 (4)
C140.079 (6)0.047 (5)0.067 (7)0.005 (4)0.003 (5)0.002 (5)
C100.054 (6)0.061 (6)0.038 (5)0.002 (5)0.007 (4)0.002 (4)
C50.044 (6)0.105 (8)0.048 (5)0.014 (6)0.006 (4)0.006 (5)
C90.072 (6)0.063 (6)0.062 (6)0.002 (5)0.008 (5)0.010 (5)
C40.047 (6)0.121 (9)0.081 (7)0.024 (7)0.004 (5)0.036 (7)
C80.095 (8)0.070 (7)0.095 (8)0.020 (7)0.023 (7)0.015 (6)
C60.066 (7)0.120 (9)0.069 (7)0.027 (7)0.002 (5)0.008 (7)
C70.079 (9)0.131 (11)0.082 (8)0.044 (8)0.007 (6)0.037 (7)
Br20.0792 (7)0.1115 (8)0.0647 (7)0.0114 (6)0.0219 (5)0.0139 (6)
O30.055 (4)0.064 (4)0.098 (5)0.000 (3)0.000 (3)0.017 (3)
O40.129 (5)0.047 (4)0.084 (5)0.013 (3)0.025 (4)0.002 (3)
N20.068 (4)0.041 (4)0.044 (4)0.001 (3)0.002 (3)0.014 (3)
C220.036 (5)0.045 (5)0.040 (4)0.003 (4)0.004 (3)0.005 (4)
C320.044 (5)0.039 (4)0.048 (5)0.002 (4)0.007 (4)0.004 (4)
C310.053 (6)0.053 (5)0.036 (5)0.004 (5)0.002 (4)0.003 (4)
C360.049 (5)0.067 (6)0.065 (6)0.008 (5)0.017 (5)0.021 (5)
C330.047 (5)0.043 (5)0.045 (5)0.004 (4)0.004 (4)0.009 (4)
C380.058 (6)0.089 (6)0.055 (6)0.028 (5)0.006 (5)0.013 (5)
C400.098 (7)0.048 (5)0.112 (9)0.017 (5)0.016 (6)0.027 (6)
C250.102 (8)0.047 (6)0.051 (6)0.018 (6)0.003 (5)0.001 (4)
C260.076 (7)0.059 (6)0.035 (5)0.003 (6)0.003 (4)0.004 (4)
C390.066 (6)0.058 (5)0.069 (6)0.010 (5)0.004 (5)0.013 (5)
C370.070 (6)0.089 (7)0.051 (6)0.025 (5)0.004 (5)0.004 (5)
C300.056 (6)0.069 (6)0.042 (5)0.009 (5)0.002 (4)0.002 (4)
C340.049 (5)0.074 (6)0.071 (7)0.015 (5)0.006 (5)0.000 (5)
C420.071 (6)0.060 (5)0.065 (6)0.011 (5)0.007 (5)0.009 (4)
C290.061 (6)0.086 (7)0.061 (6)0.016 (6)0.009 (5)0.012 (5)
C270.104 (8)0.054 (6)0.058 (6)0.003 (6)0.027 (6)0.004 (4)
C230.065 (6)0.042 (5)0.055 (5)0.003 (5)0.003 (4)0.003 (4)
C240.083 (7)0.045 (5)0.076 (6)0.012 (5)0.016 (5)0.013 (5)
C410.090 (7)0.058 (6)0.070 (6)0.005 (5)0.029 (5)0.004 (5)
C280.116 (9)0.063 (7)0.054 (6)0.031 (7)0.022 (6)0.008 (5)
C350.048 (5)0.075 (6)0.073 (7)0.013 (5)0.003 (5)0.015 (5)
Br40.1229 (9)0.0442 (5)0.1052 (8)0.0055 (5)0.0244 (6)0.0072 (5)
O70.058 (3)0.066 (4)0.060 (4)0.001 (3)0.008 (3)0.018 (3)
O80.038 (3)0.085 (4)0.080 (4)0.008 (3)0.004 (3)0.003 (3)
N40.037 (4)0.044 (4)0.052 (4)0.000 (3)0.001 (3)0.006 (3)
C750.050 (5)0.049 (5)0.051 (5)0.007 (4)0.002 (4)0.012 (4)
C740.044 (5)0.042 (4)0.035 (4)0.002 (4)0.008 (3)0.006 (3)
C760.074 (6)0.040 (5)0.092 (7)0.002 (4)0.010 (5)0.027 (5)
C730.039 (5)0.044 (5)0.053 (5)0.011 (4)0.005 (4)0.000 (4)
C650.048 (5)0.027 (4)0.065 (6)0.006 (4)0.014 (4)0.013 (4)
C690.047 (6)0.055 (6)0.108 (8)0.015 (4)0.015 (6)0.021 (6)
C640.043 (5)0.029 (4)0.063 (5)0.011 (4)0.008 (4)0.012 (4)
C810.049 (5)0.053 (5)0.082 (6)0.001 (4)0.008 (4)0.013 (5)
C780.084 (7)0.044 (5)0.062 (6)0.010 (5)0.025 (5)0.014 (5)
C790.081 (6)0.047 (5)0.071 (6)0.000 (5)0.001 (5)0.009 (5)
C800.083 (6)0.042 (5)0.071 (6)0.013 (5)0.001 (5)0.019 (5)
C670.044 (5)0.046 (5)0.102 (8)0.007 (4)0.014 (5)0.001 (5)
C660.048 (5)0.048 (5)0.071 (6)0.000 (4)0.016 (5)0.027 (4)
C680.037 (5)0.028 (4)0.084 (7)0.004 (4)0.005 (5)0.003 (4)
C830.069 (6)0.060 (5)0.057 (6)0.023 (5)0.002 (5)0.006 (4)
C840.056 (5)0.055 (5)0.075 (6)0.002 (4)0.005 (5)0.007 (5)
C720.051 (5)0.069 (6)0.051 (5)0.007 (4)0.004 (4)0.013 (4)
C770.079 (6)0.055 (6)0.078 (7)0.006 (5)0.001 (5)0.037 (5)
C700.065 (7)0.084 (7)0.075 (7)0.012 (5)0.020 (5)0.003 (6)
C710.068 (6)0.090 (7)0.055 (6)0.007 (5)0.007 (5)0.013 (5)
C820.049 (5)0.070 (6)0.069 (6)0.011 (5)0.005 (4)0.001 (5)
Br30.0455 (6)0.1376 (10)0.1382 (10)0.0112 (6)0.0114 (6)0.0444 (8)
O50.051 (3)0.063 (3)0.057 (4)0.004 (3)0.012 (3)0.008 (3)
O60.082 (4)0.052 (4)0.076 (4)0.007 (3)0.002 (3)0.016 (3)
N30.045 (4)0.035 (3)0.051 (4)0.007 (3)0.004 (3)0.000 (3)
C520.024 (4)0.041 (5)0.072 (6)0.001 (4)0.003 (4)0.010 (4)
C540.050 (5)0.051 (5)0.050 (5)0.005 (4)0.004 (4)0.010 (4)
C440.032 (5)0.044 (5)0.076 (7)0.002 (4)0.006 (4)0.000 (5)
C470.029 (5)0.044 (5)0.094 (7)0.004 (4)0.007 (4)0.019 (5)
C450.046 (5)0.063 (6)0.082 (7)0.007 (5)0.020 (5)0.006 (5)
C610.058 (5)0.070 (6)0.069 (6)0.019 (5)0.012 (4)0.004 (5)
C510.067 (6)0.044 (5)0.068 (6)0.002 (4)0.009 (5)0.006 (5)
C590.037 (5)0.074 (6)0.077 (6)0.005 (5)0.014 (5)0.016 (5)
C630.061 (5)0.060 (5)0.060 (6)0.008 (5)0.006 (4)0.011 (4)
C530.032 (4)0.050 (5)0.051 (5)0.005 (4)0.004 (4)0.001 (4)
C550.042 (5)0.070 (6)0.072 (6)0.001 (4)0.008 (4)0.002 (5)
C430.031 (4)0.036 (4)0.059 (5)0.001 (4)0.000 (4)0.003 (4)
C560.060 (6)0.071 (6)0.067 (6)0.004 (5)0.001 (5)0.003 (5)
C460.044 (5)0.048 (5)0.120 (9)0.003 (4)0.009 (6)0.001 (6)
C500.073 (6)0.070 (6)0.073 (7)0.001 (5)0.007 (5)0.025 (5)
C480.044 (5)0.049 (5)0.125 (9)0.005 (4)0.010 (6)0.032 (6)
C600.067 (6)0.044 (5)0.070 (6)0.012 (4)0.005 (5)0.005 (4)
C620.069 (6)0.055 (5)0.071 (6)0.002 (5)0.002 (5)0.022 (5)
C580.049 (6)0.090 (7)0.079 (7)0.016 (5)0.021 (5)0.019 (6)
C570.036 (5)0.074 (6)0.090 (7)0.002 (5)0.009 (5)0.032 (6)
C490.059 (6)0.090 (8)0.097 (8)0.005 (6)0.000 (6)0.037 (6)
Geometric parameters (Å, º) top
Br1—C151.911 (7)Br4—C781.932 (8)
O1—C21.354 (9)O7—C651.349 (8)
O1—H1A0.8200O7—H7B0.8200
O2—C191.406 (8)O8—C831.406 (8)
O2—C201.429 (8)O8—C821.416 (8)
N1—C181.474 (8)N4—C811.470 (8)
N1—C211.477 (8)N4—C841.472 (8)
N1—C111.488 (8)N4—C741.501 (8)
C18—C191.500 (9)C75—C761.379 (9)
C18—H18A0.9700C75—C801.396 (9)
C18—H18B0.9700C75—C741.510 (9)
C1—C21.382 (9)C74—C641.526 (9)
C1—C101.408 (9)C74—H74A0.9800
C1—C111.537 (9)C76—C771.383 (10)
C12—C131.375 (9)C76—H76A0.9300
C12—C171.395 (9)C73—C681.405 (9)
C12—C111.526 (9)C73—C721.412 (9)
C2—C31.421 (10)C73—C641.437 (9)
C11—H11A0.9800C65—C661.406 (9)
C3—C41.333 (11)C65—C641.411 (9)
C3—H3A0.9300C69—C701.357 (11)
C15—C161.358 (9)C69—C681.425 (10)
C15—C141.378 (10)C69—H69A0.9300
C21—C201.490 (9)C81—C821.498 (9)
C21—H21A0.9700C81—H81A0.9700
C21—H21B0.9700C81—H81B0.9700
C13—C141.376 (10)C78—C791.358 (10)
C13—H13A0.9300C78—C771.367 (10)
C17—C161.387 (10)C79—C801.370 (9)
C17—H17A0.9300C79—H79A0.9300
C16—H16A0.9300C80—H80A0.9300
C20—H20A0.9700C67—C661.336 (10)
C20—H20B0.9700C67—C681.421 (10)
C19—H19A0.9700C67—H67A0.9300
C19—H19B0.9700C66—H66A0.9300
C14—H14A0.9300C83—C841.519 (9)
C10—C91.415 (10)C83—H83A0.9700
C10—C51.445 (10)C83—H83B0.9700
C5—C61.398 (11)C84—H84A0.9700
C5—C41.408 (11)C84—H84B0.9700
C9—C81.391 (11)C72—C711.346 (9)
C9—H9A0.9300C72—H72A0.9300
C4—H4A0.9300C77—H77A0.9300
C8—C71.382 (13)C70—C711.422 (11)
C8—H8A0.9300C70—H70A0.9300
C6—C71.345 (13)C71—H71A0.9300
C6—H6A0.9300C82—H82A0.9700
C7—H7A0.9300C82—H82B0.9700
Br2—C361.912 (8)Br3—C571.882 (8)
O3—C231.359 (8)O5—C441.357 (8)
O3—H3B0.8200O5—H5A0.8200
O4—C411.402 (8)O6—C611.421 (8)
O4—C401.409 (9)O6—C621.421 (8)
N2—C391.480 (8)N3—C601.466 (8)
N2—C421.485 (8)N3—C631.470 (8)
N2—C321.491 (8)N3—C531.499 (8)
C22—C231.387 (9)C52—C471.422 (9)
C22—C311.429 (9)C52—C431.425 (9)
C22—C321.510 (8)C52—C511.427 (9)
C32—C331.521 (9)C54—C591.387 (9)
C32—H32A0.9800C54—C551.395 (9)
C31—C301.409 (9)C54—C531.509 (9)
C31—C261.425 (10)C44—C431.376 (9)
C36—C371.360 (10)C44—C451.391 (10)
C36—C351.364 (10)C47—C461.402 (11)
C33—C341.372 (9)C47—C481.422 (10)
C33—C381.377 (9)C45—C461.350 (10)
C38—C371.378 (10)C45—H45A0.9300
C38—H38A0.9300C61—C601.511 (9)
C40—C391.503 (10)C61—H61A0.9700
C40—H40A0.9700C61—H61B0.9700
C40—H40B0.9700C51—C501.363 (9)
C25—C241.344 (10)C51—H51A0.9300
C25—C261.399 (10)C59—C581.386 (10)
C25—H25A0.9300C59—H59A0.9300
C26—C271.423 (10)C63—C621.533 (9)
C39—H39A0.9700C63—H63A0.9700
C39—H39B0.9700C63—H63B0.9700
C37—H37A0.9300C53—C431.522 (9)
C30—C291.382 (10)C53—H53A0.9800
C30—H30A0.9300C55—C561.382 (10)
C34—C351.386 (10)C55—H55A0.9300
C34—H34A0.9300C56—C571.369 (10)
C42—C411.503 (9)C56—H56A0.9300
C42—H42A0.9700C46—H46A0.9300
C42—H42B0.9700C50—C491.392 (10)
C29—C281.393 (11)C50—H50A0.9300
C29—H29A0.9300C48—C491.380 (11)
C27—C281.352 (11)C48—H48A0.9300
C27—H27A0.9300C60—H60A0.9700
C23—C241.401 (9)C60—H60B0.9700
C24—H24A0.9300C62—H62A0.9700
C41—H41A0.9700C62—H62B0.9700
C41—H41B0.9700C58—C571.380 (11)
C28—H28A0.9300C58—H58A0.9300
C35—H35A0.9300C49—H49A0.9300
C2—O1—H1A109.5C65—O7—H7B109.5
C19—O2—C20109.3 (5)C83—O8—C82110.6 (5)
C18—N1—C21107.3 (5)C81—N4—C84108.8 (5)
C18—N1—C11109.0 (5)C81—N4—C74113.5 (5)
C21—N1—C11114.4 (5)C84—N4—C74109.7 (5)
N1—C18—C19110.5 (6)C76—C75—C80118.4 (7)
N1—C18—H18A109.5C76—C75—C74119.8 (7)
C19—C18—H18A109.5C80—C75—C74121.8 (6)
N1—C18—H18B109.5N4—C74—C75113.9 (5)
C19—C18—H18B109.5N4—C74—C64109.4 (5)
H18A—C18—H18B108.1C75—C74—C64110.2 (5)
C2—C1—C10119.7 (7)N4—C74—H74A107.7
C2—C1—C11119.9 (7)C75—C74—H74A107.7
C10—C1—C11120.4 (7)C64—C74—H74A107.7
C13—C12—C17118.5 (7)C75—C76—C77121.4 (8)
C13—C12—C11120.0 (7)C75—C76—H76A119.3
C17—C12—C11121.5 (7)C77—C76—H76A119.3
O1—C2—C1125.2 (7)C68—C73—C72118.2 (7)
O1—C2—C3114.1 (7)C68—C73—C64120.3 (7)
C1—C2—C3120.7 (8)C72—C73—C64121.6 (7)
N1—C11—C12112.0 (5)O7—C65—C66116.9 (7)
N1—C11—C1111.2 (5)O7—C65—C64123.1 (7)
C12—C11—C1112.8 (5)C66—C65—C64120.0 (8)
N1—C11—H11A106.8C70—C69—C68122.8 (9)
C12—C11—H11A106.8C70—C69—H69A118.6
C1—C11—H11A106.8C68—C69—H69A118.6
C4—C3—C2118.9 (8)C65—C64—C73117.8 (7)
C4—C3—H3A120.6C65—C64—C74121.1 (7)
C2—C3—H3A120.6C73—C64—C74120.9 (6)
C16—C15—C14121.7 (7)N4—C81—C82110.0 (6)
C16—C15—Br1121.0 (7)N4—C81—H81A109.7
C14—C15—Br1117.2 (6)C82—C81—H81A109.7
N1—C21—C20110.1 (6)N4—C81—H81B109.7
N1—C21—H21A109.6C82—C81—H81B109.7
C20—C21—H21A109.6H81A—C81—H81B108.2
N1—C21—H21B109.6C79—C78—C77122.1 (8)
C20—C21—H21B109.6C79—C78—Br4119.3 (7)
H21A—C21—H21B108.1C77—C78—Br4118.6 (6)
C12—C13—C14122.6 (7)C78—C79—C80119.7 (8)
C12—C13—H13A118.7C78—C79—H79A120.1
C14—C13—H13A118.7C80—C79—H79A120.1
C16—C17—C12119.3 (7)C79—C80—C75120.2 (7)
C16—C17—H17A120.4C79—C80—H80A119.9
C12—C17—H17A120.4C75—C80—H80A119.9
C15—C16—C17120.4 (7)C66—C67—C68120.4 (8)
C15—C16—H16A119.8C66—C67—H67A119.8
C17—C16—H16A119.8C68—C67—H67A119.8
O2—C20—C21113.3 (6)C67—C66—C65122.1 (8)
O2—C20—H20A108.9C67—C66—H66A118.9
C21—C20—H20A108.9C65—C66—H66A118.9
O2—C20—H20B108.9C73—C68—C67119.3 (8)
C21—C20—H20B108.9C73—C68—C69118.6 (8)
H20A—C20—H20B107.7C67—C68—C69122.0 (8)
O2—C19—C18111.2 (6)O8—C83—C84111.0 (6)
O2—C19—H19A109.4O8—C83—H83A109.4
C18—C19—H19A109.4C84—C83—H83A109.4
O2—C19—H19B109.4O8—C83—H83B109.4
C18—C19—H19B109.4C84—C83—H83B109.4
H19A—C19—H19B108.0H83A—C83—H83B108.0
C13—C14—C15117.6 (7)N4—C84—C83110.7 (6)
C13—C14—H14A121.2N4—C84—H84A109.5
C15—C14—H14A121.2C83—C84—H84A109.5
C1—C10—C9122.8 (8)N4—C84—H84B109.5
C1—C10—C5120.2 (8)C83—C84—H84B109.5
C9—C10—C5116.9 (8)H84A—C84—H84B108.1
C6—C5—C4125.2 (10)C71—C72—C73121.3 (8)
C6—C5—C10118.8 (10)C71—C72—H72A119.3
C4—C5—C10116.0 (8)C73—C72—H72A119.3
C8—C9—C10120.6 (9)C78—C77—C76118.1 (7)
C8—C9—H9A119.7C78—C77—H77A121.0
C10—C9—H9A119.7C76—C77—H77A121.0
C3—C4—C5124.5 (9)C69—C70—C71117.0 (8)
C3—C4—H4A117.7C69—C70—H70A121.5
C5—C4—H4A117.7C71—C70—H70A121.5
C7—C8—C9121.3 (10)C72—C71—C70122.0 (8)
C7—C8—H8A119.3C72—C71—H71A119.0
C9—C8—H8A119.3C70—C71—H71A119.0
C7—C6—C5123.0 (10)O8—C82—C81112.4 (6)
C7—C6—H6A118.5O8—C82—H82A109.1
C5—C6—H6A118.5C81—C82—H82A109.1
C6—C7—C8119.2 (10)O8—C82—H82B109.1
C6—C7—H7A120.4C81—C82—H82B109.1
C8—C7—H7A120.4H82A—C82—H82B107.9
C23—O3—H3B109.5C44—O5—H5A109.5
C41—O4—C40109.2 (6)C61—O6—C62109.1 (5)
C39—N2—C42108.1 (6)C60—N3—C63109.1 (5)
C39—N2—C32113.2 (5)C60—N3—C53108.9 (5)
C42—N2—C32109.6 (5)C63—N3—C53112.7 (5)
C23—C22—C31118.4 (7)C47—C52—C43119.2 (7)
C23—C22—C32121.6 (6)C47—C52—C51116.7 (7)
C31—C22—C32120.0 (6)C43—C52—C51124.0 (7)
N2—C32—C22111.3 (5)C59—C54—C55118.7 (7)
N2—C32—C33113.9 (5)C59—C54—C53119.4 (7)
C22—C32—C33112.7 (5)C55—C54—C53121.9 (7)
N2—C32—H32A106.1O5—C44—C43122.2 (7)
C22—C32—H32A106.1O5—C44—C45116.0 (7)
C33—C32—H32A106.1C43—C44—C45121.8 (8)
C30—C31—C26117.8 (7)C46—C47—C52119.7 (8)
C30—C31—C22122.6 (7)C46—C47—C48121.1 (8)
C26—C31—C22119.6 (7)C52—C47—C48119.2 (8)
C37—C36—C35122.1 (8)C46—C45—C44121.0 (8)
C37—C36—Br2121.0 (7)C46—C45—H45A119.5
C35—C36—Br2116.7 (6)C44—C45—H45A119.5
C34—C33—C38118.1 (7)O6—C61—C60112.0 (6)
C34—C33—C32119.7 (7)O6—C61—H61A109.2
C38—C33—C32122.1 (7)C60—C61—H61A109.2
C33—C38—C37121.2 (7)O6—C61—H61B109.2
C33—C38—H38A119.4C60—C61—H61B109.2
C37—C38—H38A119.4H61A—C61—H61B107.9
O4—C40—C39112.8 (7)C50—C51—C52122.5 (8)
O4—C40—H40A109.0C50—C51—H51A118.8
C39—C40—H40A109.0C52—C51—H51A118.8
O4—C40—H40B109.0C58—C59—C54120.2 (8)
C39—C40—H40B109.0C58—C59—H59A119.9
H40A—C40—H40B107.8C54—C59—H59A119.9
C24—C25—C26122.2 (8)N3—C63—C62109.7 (6)
C24—C25—H25A118.9N3—C63—H63A109.7
C26—C25—H25A118.9C62—C63—H63A109.7
C25—C26—C27122.7 (9)N3—C63—H63B109.7
C25—C26—C31118.3 (8)C62—C63—H63B109.7
C27—C26—C31119.0 (8)H63A—C63—H63B108.2
N2—C39—C40109.8 (6)N3—C53—C54112.9 (6)
N2—C39—H39A109.7N3—C53—C43110.1 (5)
C40—C39—H39A109.7C54—C53—C43111.6 (5)
N2—C39—H39B109.7N3—C53—H53A107.3
C40—C39—H39B109.7C54—C53—H53A107.3
H39A—C39—H39B108.2C43—C53—H53A107.3
C36—C37—C38118.8 (8)C56—C55—C54120.3 (7)
C36—C37—H37A120.6C56—C55—H55A119.9
C38—C37—H37A120.6C54—C55—H55A119.9
C29—C30—C31121.3 (8)C44—C43—C52118.1 (7)
C29—C30—H30A119.4C44—C43—C53120.9 (7)
C31—C30—H30A119.4C52—C43—C53120.9 (6)
C33—C34—C35121.7 (8)C57—C56—C55120.8 (8)
C33—C34—H34A119.1C57—C56—H56A119.6
C35—C34—H34A119.1C55—C56—H56A119.6
N2—C42—C41110.3 (6)C45—C46—C47120.0 (8)
N2—C42—H42A109.6C45—C46—H46A120.0
C41—C42—H42A109.6C47—C46—H46A120.0
N2—C42—H42B109.6C51—C50—C49120.9 (8)
C41—C42—H42B109.6C51—C50—H50A119.5
H42A—C42—H42B108.1C49—C50—H50A119.5
C30—C29—C28120.4 (8)C49—C48—C47121.8 (8)
C30—C29—H29A119.8C49—C48—H48A119.1
C28—C29—H29A119.8C47—C48—H48A119.1
C28—C27—C26121.3 (9)N3—C60—C61110.2 (6)
C28—C27—H27A119.3N3—C60—H60A109.6
C26—C27—H27A119.3C61—C60—H60A109.6
O3—C23—C22123.3 (7)N3—C60—H60B109.6
O3—C23—C24115.5 (8)C61—C60—H60B109.6
C22—C23—C24121.2 (8)H60A—C60—H60B108.1
C25—C24—C23120.1 (8)O6—C62—C63111.8 (6)
C25—C24—H24A119.9O6—C62—H62A109.3
C23—C24—H24A119.9C63—C62—H62A109.3
O4—C41—C42112.4 (6)O6—C62—H62B109.3
O4—C41—H41A109.1C63—C62—H62B109.3
C42—C41—H41A109.1H62A—C62—H62B107.9
O4—C41—H41B109.1C57—C58—C59120.5 (8)
C42—C41—H41B109.1C57—C58—H58A119.7
H41A—C41—H41B107.9C59—C58—H58A119.7
C27—C28—C29120.2 (9)C56—C57—C58119.3 (8)
C27—C28—H28A119.9C56—C57—Br3120.9 (8)
C29—C28—H28A119.9C58—C57—Br3119.7 (7)
C36—C35—C34117.9 (7)C48—C49—C50118.8 (9)
C36—C35—H35A121.1C48—C49—H49A120.6
C34—C35—H35A121.1C50—C49—H49A120.6
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
O1—H1A···N10.821.922.600 (7)139
O3—H3B···N20.821.922.601 (7)140
O5—H5A···N30.821.912.612 (7)142
O7—H7B···N40.821.932.620 (7)142
C25—H25A···O4i0.932.583.473 (10)162
C46—H46A···O6ii0.932.573.371 (10)144
C55—H55A···O50.932.593.305 (9)134
C67—H67A···O8iii0.932.413.208 (9)143
Symmetry codes: (i) x, y+1, z; (ii) x, y1, z; (iii) x+1, y, z.

Experimental details

Crystal data
Chemical formulaC21H20BrNO2
Mr398.28
Crystal system, space groupTriclinic, P1
Temperature (K)293
a, b, c (Å)10.514 (2), 10.700 (2), 34.002 (7)
α, β, γ (°)82.32 (3), 89.43 (3), 88.67 (3)
V3)3789.8 (13)
Z8
Radiation typeMo Kα
µ (mm1)2.18
Crystal size (mm)0.20 × 0.20 × 0.20
Data collection
DiffractometerRigaku Mercury2 (2x2 bin mode)
diffractometer
Absorption correctionMulti-scan
(CrystalClear; Rigaku, 2005)
Tmin, Tmax0.822, 1.000
No. of measured, independent and
observed [I > 2σ(I)] reflections
26170, 13194, 5620
Rint0.094
(sin θ/λ)max1)0.595
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.083, 0.192, 1.03
No. of reflections13194
No. of parameters901
H-atom treatmentH-atom parameters constrained
Δρmax, Δρmin (e Å3)0.59, 0.58

Computer programs: CrystalClear (Rigaku, 2005), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), SHELXTL (Sheldrick, 2008).

Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
O1—H1A···N10.821.922.600 (7)139.4
O3—H3B···N20.821.922.601 (7)140.0
O5—H5A···N30.821.912.612 (7)142.4
O7—H7B···N40.821.932.620 (7)141.7
C25—H25A···O4i0.932.583.473 (10)161.6
C46—H46A···O6ii0.932.573.371 (10)144.0
C55—H55A···O50.932.593.305 (9)134.2
C67—H67A···O8iii0.932.413.208 (9)143.3
Symmetry codes: (i) x, y+1, z; (ii) x, y1, z; (iii) x+1, y, z.
 

Acknowledgements

The author is grateful to the Starter Fund of Nanjing University of Chinese Medicine.

References

First citationGardiner, M. & Raston, C. (1997). Coord. Chem. Rev. 166, 1–34.  Web of Science CrossRef CAS Google Scholar
First citationGutsche, C. D. & Nam, K. C. (1998). J. Am. Chem. Soc. 110, 6153–6162.  CrossRef Web of Science Google Scholar
First citationRigaku (2005). CrystalClear. Rigaku Corporation, Tokyo, Japan.  Google Scholar
First citationSheldrick, G. M. (2008). Acta Cryst. A64, 112–122.  Web of Science CrossRef CAS IUCr Journals Google Scholar

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