24×(3分之2+6分之5-4分之3)（计算）
=24×3分之2+24×6分之5-24×4分之3=16+20-18=18
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3分之2+6分之5=6分之9 -4分之3=24分之18 24*24分之18=18
=24×4分之3=18
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你可能喜欢PMCID: PMC29801913-Acetyl-6-chloro-4-phenyl&#x000quinolin-2(1H)-one,a ,a ,b ,b and
c,*bOrganic Chemistry Division, School of Advanced Sciences, VIT University, Vellore 632 014, IndiacDepartment of Food science and Technology, Faculty of Agriculture, University of Ruhuna, Mapalana, Kamburupitiya 81100, Sri LankaCorrespondence e-mail:
The title compound, C17H12ClNO2, crystallizes with two mol&#x000ecules in the asymmetric unit. The main conformational difference between these two mol&#x000ecules is the dihedral angle between the phenyl ring and the quinoline ring system [70.5 (1)° and 65.5 (1) Å]. The crystal packing is stabilized by N—HO hydrogen bonds.For general background, see: Cooper et al. (1992); Gaudio et al. (1994); Gordeev et al. (1996).
Crystal data
C17H12ClNO2
r = 297.73Monoclinic,
a = 10.043 (5) Å
b = 18.663 (9) Å
c = 15.537 (7) Åβ = 91.811 (5)°
V = 2911 (2) Å3
Z = 8Mo Kα radiation&#x003 = 0.27 mm−1
T = 293 K0.17 × 0.14 × 0.11 mm
Data collection
Nonius MACH-3 diffractometerAbsorption correction: ψ scan (North et al., 1968) T
min = 0.955, T
max = 0.9675771 measured reflections5104 independent reflections2567 reflections with I > 2σ(I)
int = 0.0152 standard reflections every 60 minintensity decay: none
Refinement
2 > 2σ(F
2)] = 0.041
2) = 0.123
S = 1.005104 reflections389 parametersH atoms treated by a mixture of independent and constrained refinementΔρmax = 0.22 e Å−3
Δρmin = &#x e Å−3
Data collection: CAD-4 EXPRESS (Enraf–Nonius, 1994); cell refinement: CAD-4 EXPRESS; data reduction: XCAD4 (Harms & Wocadlo, 1996); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: PLATON (Spek, 2009); software used to prepare material for publication: SHELXL97.Hydrogen-bond geometry (Å, °)Crystal structure: contains datablocks global, I. DOI:
(26K, cif)Structure factors: contains datablocks I. DOI:
(245K, hkl)Additional supplementary materials: ; ;
SN thanks the DST for the FIST programme and VV thanks the DST-India for funding through the Young Scientist-Fast Track Proposal.
Experimental
A mixture of 2-amino-5-chlorobenzophenone (2.3 g 0.01 mol) and acetylacetone (1 g, 0.01 mol) with 0.15 ml conc. HCl taken in a beaker was subjected to
microwave irradiation for about 6 min. After completion of the reaction (TLC),
the reaction mixture was washed with saturated solution NaHCO3 (10 ml) and
then dried. After that it was washed with petroleum ether and recrystallized
with ethanol. m.p.224&#x °C.
Refinement
The amino H-atom was located in a difference Fourier map, and was freely
refined. The C-bound H atoms were placed at calculated positions
and allowed to ride on their carrier atoms with C—H = 0.93&#x Å and
Uiso = 1.2Ueq(C) for CH group, and 1.5Ueq for CH3
groups.Figures The molecular structure of the title compound, showing 50% probability displacement ellipsoids and the atom-numbering scheme.Crystal data C17H12ClNO2F(000) = 1232Mr = 297.73Dx = 1.359 Mg m−3Monoclinic, P21/nMo Kα radiation, &#x003 = 0.71069 Åa = 10.043 (5) ÅCell parameters from 25 reflectionsb = 18.663 (9) Åθ = 2–25°c = 15.537 (7) ŵ = 0.27 mm−1β = 91.811 (5)°T = 293 KV = 2911 (2)
Å3Block, colourlessZ = 80.17 × 0.14 × 0.11 mmData collection Nonius MACH-3 diffractometer2567 reflections with I > 2σ(I)Radiation source: fine-focus sealed tubeRint = 0.015graphiteθmax = 25.0°, θmin = 2.2°ω–2θ scansh = 0→11Absorption correction: ψ scan (North et al.,
1968)k = −1→22Tmin = 0.955, Tmax = 0.967l = −18→185771 measured reflections2 standard reflections every 60 min5104 independent reflections intensity decay: noneRefinement Refinement on F2Primary atom site location: structure-invariant direct methodsLeast-squares matrix: fullSecondary atom site location: difference Fourier mapR[F2 > 2σ(F2)] = 0.041Hydrogen site location: inferred from neighbouring siteswR(F2) = 0.123H atoms treated by a mixture of independent and constrained refinementS = 1.00w = 1/[σ2(Fo2) + (0.0478P)2 + 0.722P]
where P = (Fo2 + 2Fc2)/35104 reflections(Δ/σ)max < 0.001389 parametersΔρmax = 0.22 e Å−30 restraintsΔρmin = &#x e Å−3Special details 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
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) xyzUiso*/UeqH10.316 (3)0.4766 (17)0.3548 (19)0.084 (10)*H20.433 (3)0.4103 (15)0.4718 (18)0.073 (9)*C20.2436 (3)0.38557 (15)0.48154 (18)0.0546 (7)C30.1547 (3)0.34166 (14)0.53187 (16)0.0490 (7)C40.2019 (3)0.29962 (14)0.59716 (16)0.0478 (7)C50.3441 (3)0.29580 (14)0.61547 (17)0.0485 (7)C60.4299 (3)0.33733 (14)0.56559 (17)0.0503 (7)C70.5675 (3)0.33402 (16)0.5801 (2)0.0637 (8)H70.62330.36150.54660.076*C80.6211 (3)0.29074 (18)0.6431 (2)0.0702 (9)H80.71290.28880.65280.084*C90.5373 (3)0.24975 (17)0.69226 (19)0.0657 (9)C100.4021 (3)0.25169 (16)0.67917 (18)0.0583 (8)H100.34820.22340.71290.070*C110.1106 (2)0.25720 (14)0.65164 (17)0.0474 (7)C120.0419 (3)0.19869 (16)0.6198 (2)0.0678 (9)H120.05090.18500.56280.081*C13&#x0 (3)0.16005 (18)0.6726 (3)0.0794 (10)H13&#x50.12060.65070.095*C14&#x5 (3)0.17966 (19)0.7567 (2)0.0748 (10)H14&#x20.15370.79190.090*C150.0141 (3)0.23736 (19)0.7888 (2)0.0763 (10)H150.00560.25050.84610.092*C160.0953 (3)0.27593 (16)0.7369 (2)0.0666 (9)H160.14090.31540.75930.080*C170.0084 (3)0.34993 (18)0.51066 (19)0.0617 (8)C18&#x6 (4)0.4092 (2)0.5505 (3)0.1200 (16)H18A&#x80.41650.52090.180*H18B&#x00.45200.54710.180*H18C&#x10.39810.60980.180*O30.20241 (19)0.42606 (11)0.42292 (13)0.0695 (6)C220.5109 (3)0.48911 (15)0.33411 (18)0.0540 (7)C230.6000 (3)0.51645 (14)0.26931 (17)0.0509 (7)C240.5525 (3)0.55259 (14)0.19914 (17)0.0496 (7)C250.4099 (3)0.56463 (15)0.18733 (17)0.0516 (7)C260.3239 (3)0.53486 (14)0.24734 (18)0.0510 (7)C270.1863 (3)0.54169 (16)0.2368 (2)0.0623 (8)H270.13070.52040.27610.075*C280.1325 (3)0.57966 (17)0.1688 (2)0.0680 (9)H280.04060.58460.16180.082*C290.2171 (3)0.61076 (17)0.11031 (19)0.0671 (9)C300.3526 (3)0.60242 (17)0.11801 (19)0.0645 (8)H300.40680.62210.07670.077*C310.6424 (3)0.57753 (16)0.12980 (17)0.0527 (7)C320.7112 (3)0.52777 (19)0.0823 (2)0.0745 (9)H320.70180.47920.09380.089*C330.7940 (4)0.5498 (2)0.0177 (2)0.0924 (12)H330.84030.5160&#x60.111*C340.8076 (3)0.6212 (3)&#x1 (2)0.0867 (12)H340.86270.6358&#x70.104*C350.7409 (3)0.6706 (2)0.0460 (2)0.0774 (10)H350.75100.71910.03420.093*C360.6580 (3)0.64907 (17)0.11062 (19)0.0648 (8)H360.61210.68330.14150.078*C370.7460 (3)0.50148 (17)0.28466 (17)0.0565 (8)C380.7913 (3)0.42529 (17)0.2902 (3)0.0913 (11)H38A0.76610.40080.23790.137*H38B0.75050.40230.33790.137*H38C0.88640.42390.29830.137*O40.5515 (2)0.45877 (11)0.40079 (13)0.0677 (6)N10.3760 (2)0.38020 (13)0.50155 (15)0.0564 (6)N20.3779 (3)0.49874 (13)0.31750 (15)0.0553 (6)O1&#x7 (3)0.30921 (15)0.46303 (19)0.1134 (9)O20.8246 (2)0.55021 (12)0.28979 (15)0.0813 (7)Cl10.60397 (9)0.19417 (7)0.77191 (7)0.1139 (4)Cl20.15123 (9)0.65908 (6)0.02361 (6)0.0999 (4)Atomic displacement parameters (Å2) U11U22U33U12U13U23C20.060 (2)0.0565 (19)0.0479 (17)&#x4 (15)0.0101 (15)0.0036 (15)C30.0520 (16)0.0511 (17)0.0443 (15)&#x6 (14)0.0084 (13)0.0003 (14)C40.0523 (17)0.0437 (16)0.0479 (16)&#x7 (13)0.0105 (13)&#x0 (13)C50.0505 (17)0.0454 (16)0.0501 (16)&#x4 (14)0.0107 (13)&#x8 (14)C60.0542 (18)0.0470 (16)0.0501 (17)&#x5 (14)0.0089 (14)&#x3 (14)C70.0529 (19)0.069 (2)0.070 (2)&#x5 (16)0.0154 (16)0.0013 (17)C80.0497 (18)0.085 (2)0.076 (2)&#x6 (18)0.0037 (16)0.007 (2)C90.0530 (19)0.076 (2)0.069 (2)0.0034 (16)0.0095 (16)0.0154 (17)C100.0526 (18)0.0593 (19)0.0640 (19)&#x7 (15)0.0158 (15)0.0086 (16)C110.0426 (15)0.0479 (17)0.0521 (17)0.0028 (13)0.0079 (13)0.0070 (14)C120.068 (2)0.066 (2)0.069 (2)&#x0 (18)&#x3 (16)0.0054 (17)C130.062 (2)0.071 (2)0.104 (3)&#x3 (18)&#x (2)0.023 (2)C140.0497 (19)0.079 (3)0.096 (3)0.0066 (18)0.0165 (18)0.040 (2)C150.086 (2)0.070 (2)0.075 (2)0.005 (2)0.031 (2)0.0133 (19)C160.075 (2)0.0580 (19)0.069 (2)&#x8 (16)0.0233 (17)0.0036 (16)C170.061 (2)0.070 (2)0.0540 (19)&#x1 (18)0.0008 (16)0.0155 (17)C180.062 (2)0.148 (4)0.150 (4)0.021 (2)0.007 (2)&#x (3)O30.0667 (13)0.0785 (15)0.0636 (13)&#x0 (11)0.0064 (11)0.0250 (12)C220.065 (2)0.0456 (17)0.0517 (19)&#x3 (15)0.0096 (15)0.0025 (14)C230.0564 (18)0.0438 (16)0.0529 (17)&#x1 (14)0.0064 (14)0.0009 (14)C240.0512 (17)0.0461 (17)0.0520 (17)&#x7 (13)0.0084 (14)&#x5 (14)C250.0525 (17)0.0527 (17)0.0503 (17)&#x0 (14)0.0112 (14)0.0027 (14)C260.0569 (18)0.0448 (16)0.0520 (17)&#x3 (14)0.0137 (14)0.0016 (14)C270.0556 (19)0.066 (2)0.066 (2)&#x8 (16)0.0230 (16)0.0043 (17)C280.0487 (18)0.078 (2)0.078 (2)0.0020 (17)0.0134 (17)0.0088 (19)C290.055 (2)0.078 (2)0.069 (2)0.0055 (16)0.0119 (16)0.0189 (17)C300.0538 (19)0.081 (2)0.0591 (19)&#x9 (16)0.0145 (15)0.0191 (17)C310.0457 (16)0.0646 (19)0.0481 (16)&#x5 (15)0.0068 (13)0.0030 (15)C320.071 (2)0.077 (2)0.076 (2)&#x8 (18)0.0191 (19)&#x5 (19)C330.083 (3)0.122 (3)0.074 (2)0.002 (2)0.034 (2)&#x (2)C340.057 (2)0.139 (4)0.064 (2)&#x (2)0.0140 (17)0.021 (2)C350.061 (2)0.093 (3)0.079 (2)&#x4 (19)0.0078 (18)0.029 (2)C360.0572 (19)0.070 (2)0.068 (2)&#x5 (16)0.0098 (16)0.0126 (17)C370.0568 (19)0.058 (2)0.0544 (18)&#x9 (16)0.0008 (14)0.0053 (15)C380.072 (2)0.064 (2)0.138 (3)0.0064 (19)&#x (2)0.011 (2)O40.0733 (14)0.0715 (14)0.0584 (13)&#x3 (11)0.0020 (11)0.0184 (11)N10.0574 (16)0.0558 (16)0.0566 (16)&#x9 (13)0.0096 (13)0.0084 (13)N20.0586 (17)0.0535 (15)0.0546 (15)&#x6 (13)0.0168 (13)0.0062 (12)O10.099 (2)0.107 (2)0.130 (2)&#x9 (17)&#x4 (17)&#x3 (18)O20.0640 (14)0.0715 (15)0.1075 (18)&#x5 (12)&#x2 (13)0.0025 (13)Cl10.0605 (6)0.1552 (10)0.1260 (9)0.0132 (6)0.0028 (5)0.0715 (8)Cl20.0609 (5)0.1354 (9)0.1034 (7)0.0066 (5)0.0018 (5)0.0541 (7)Geometric parameters (Å, °) C2—O31.244 (3)C22—N21.365 (4)C2—N11.360 (4)C22—C231.460 (4)C2—C31.457 (4)C23—C241.356 (4)C3—C41.356 (3)C23—C371.504 (4)C3—C171.504 (4)C24—C251.455 (4)C4—C51.449 (4)C24—C311.501 (4)C4—C111.494 (3)C25—C301.397 (4)C5—C101.400 (4)C25—C261.405 (4)C5—C61.410 (4)C26—N21.378 (3)C6—N11.374 (3)C26—C271.393 (4)C6—C71.395 (4)C27—C281.369 (4)C7—C81.366 (4)C27—H270.9300C7—H70.9300C28—C291.390 (4)C8—C91.385 (4)C28—H280.9300C8—H80.9300C29—C301.371 (4)C9—C101.367 (4)C29—Cl21.735 (3)C9—Cl11.733 (3)C30—H300.9300C10—H100.9300C31—C361.378 (4)C11—C121.375 (4)C31—C321.385 (4)C11—C161.383 (4)C32—C331.385 (4)C12—C131.389 (4)C32—H320.9300C12—H120.9300C33—C341.368 (5)C13—C141.368 (5)C33—H330.9300C13—H130.9300C34—C351.358 (5)C14—C151.364 (4)C34—H340.9300C14—H140.9300C35—C361.384 (4)C15—C161.370 (4)C35—H350.9300C15—H150.9300C36—H360.9300C16—H160.9300C37—O21.206 (3)C17—O11.190 (3)C37—C381.495 (4)C17—C181.459 (5)C38—H38A0.9600C18—H18A0.9600C38—H38B0.9600C18—H18B0.9600C38—H38C0.9600C18—H18C0.9600N1—H20.93 (3)C22—O41.238 (3)N2—H10.96 (3)O3—C2—N1120.8 (3)C24—C23—C22121.4 (3)O3—C2—C3122.6 (3)C24—C23—C37122.5 (2)N1—C2—C3116.5 (3)C22—C23—C37116.2 (3)C4—C3—C2121.4 (3)C23—C24—C25119.9 (2)C4—C3—C17122.6 (2)C23—C24—C31121.8 (2)C2—C3—C17115.8 (2)C25—C24—C31118.3 (2)C3—C4—C5119.6 (2)C30—C25—C26117.7 (3)C3—C4—C11121.6 (2)C30—C25—C24123.7 (2)C5—C4—C11118.8 (2)C26—C25—C24118.6 (3)C10—C5—C6117.6 (3)N2—C26—C27120.1 (2)C10—C5—C4123.6 (2)N2—C26—C25118.9 (3)C6—C5—C4118.7 (3)C27—C26—C25120.9 (3)N1—C6—C7120.6 (3)C28—C27—C26120.3 (3)N1—C6—C5119.0 (3)C28—C27—H27119.9C7—C6—C5120.5 (3)C26—C27—H27119.9C8—C7—C6120.5 (3)C27—C28—C29119.1 (3)C8—C7—H7119.8C27—C28—H28120.5C6—C7—H7119.8C29—C28—H28120.5C7—C8—C9119.3 (3)C30—C29—C28121.4 (3)C7—C8—H8120.3C30—C29—Cl2118.7 (2)C9—C8—H8120.3C28—C29—Cl2119.9 (2)C10—C9—C8121.4 (3)C29—C30—C25120.6 (3)C10—C9—Cl1118.8 (2)C29—C30—H30119.7C8—C9—Cl1119.8 (2)C25—C30—H30119.7C9—C10—C5120.7 (3)C36—C31—C32118.2 (3)C9—C10—H10119.7C36—C31—C24122.0 (3)C5—C10—H10119.7C32—C31—C24119.8 (3)C12—C11—C16118.4 (3)C31—C32—C33120.5 (3)C12—C11—C4121.8 (3)C31—C32—H32119.7C16—C11—C4119.8 (2)C33—C32—H32119.7C11—C12—C13120.2 (3)C34—C33—C32120.1 (3)C11—C12—H12119.9C34—C33—H33120.0C13—C12—H12119.9C32—C33—H33120.0C14—C13—C12120.3 (3)C35—C34—C33120.1 (3)C14—C13—H13119.8C35—C34—H34120.0C12—C13—H13119.8C33—C34—H34120.0C15—C14—C13119.8 (3)C34—C35—C36120.2 (3)C15—C14—H14120.1C34—C35—H35119.9C13—C14—H14120.1C36—C35—H35119.9C14—C15—C16120.2 (3)C31—C36—C35120.9 (3)C14—C15—H15119.9C31—C36—H36119.6C16—C15—H15119.9C35—C36—H36119.6C15—C16—C11121.2 (3)O2—C37—C38121.1 (3)C15—C16—H16119.4O2—C37—C23120.2 (3)C11—C16—H16119.4C38—C37—C23118.7 (3)O1—C17—C18121.5 (3)C37—C38—H38A109.5O1—C17—C3120.7 (3)C37—C38—H38B109.5C18—C17—C3117.7 (3)H38A—C38—H38B109.5C17—C18—H18A109.5C37—C38—H38C109.5C17—C18—H18B109.5H38A—C38—H38C109.5H18A—C18—H18B109.5H38B—C38—H38C109.5C17—C18—H18C109.5C2—N1—C6124.6 (2)H18A—C18—H18C109.5C2—N1—H2116.8 (18)H18B—C18—H18C109.5C6—N1—H2118.4 (18)O4—C22—N2120.9 (2)C22—N2—C26124.9 (2)O4—C22—C23123.0 (3)C22—N2—H1118.6 (18)N2—C22—C23116.2 (3)C26—N2—H1116.4 (18)O3—C2—C3—C4&#x (3)C22—C23—C24—C25&#x (4)N1—C2—C3—C42.2 (4)C37—C23—C24—C25179.2 (3)O3—C2—C3—C17&#x (4)C22—C23—C24—C31&#x (2)N1—C2—C3—C17178.2 (3)C37—C23—C24—C312.6 (4)C2—C3—C4—C5&#x (4)C23—C24—C25—C30178.7 (3)C17—C3—C4—C5&#x (3)C31—C24—C25—C30&#x (4)C2—C3—C4—C11177.0 (2)C23—C24—C25—C26&#x (4)C17—C3—C4—C111.3 (4)C31—C24—C25—C26173.4 (2)C3—C4—C5—C10&#x (3)C30—C25—C26—N2&#x (2)C11—C4—C5—C103.2 (4)C24—C25—C26—N23.4 (4)C3—C4—C5—C61.3 (4)C30—C25—C26—C271.3 (4)C11—C4—C5—C6&#x (2)C24—C25—C26—C27&#x (3)C10—C5—C6—N1178.9 (2)N2—C26—C27—C28177.7 (3)C4—C5—C6—N10.2 (4)C25—C26—C27—C28&#x (4)C10—C5—C6—C7&#x (4)C26—C27—C28—C290.4 (5)C4—C5—C6—C7&#x (2)C27—C28—C29—C301.9 (5)N1—C6—C7—C8&#x (3)C27—C28—C29—Cl2180.0 (2)C5—C6—C7—C8&#x (4)C28—C29—C30—C25&#x (5)C6—C7—C8—C90.4 (5)Cl2—C29—C30—C25179.3 (2)C7—C8—C9—C100.0 (5)C26—C25—C30—C291.0 (4)C7—C8—C9—Cl1179.6 (2)C24—C25—C30—C29179.0 (3)C8—C9—C10—C5&#x (5)C23—C24—C31—C36&#x (3)Cl1—C9—C10—C5&#x (2)C25—C24—C31—C3665.5 (4)C6—C5—C10—C90.4 (4)C23—C24—C31—C3263.0 (4)C4—C5—C10—C9178.9 (3)C25—C24—C31—C32&#x (3)C3—C4—C11—C1270.2 (4)C36—C31—C32—C330.4 (5)C5—C4—C11—C12&#x (3)C24—C31—C32—C33179.6 (3)C3—C4—C11—C16&#x (3)C31—C32—C33—C34&#x (5)C5—C4—C11—C1668.7 (3)C32—C33—C34—C350.5 (6)C16—C11—C12—C130.3 (4)C33—C34—C35—C36&#x (5)C4—C11—C12—C13179.3 (3)C32—C31—C36—C35&#x (4)C11—C12—C13—C14&#x (5)C24—C31—C36—C35&#x (3)C12—C13—C14—C15&#x (5)C34—C35—C36—C310.5 (5)C13—C14—C15—C160.6 (5)C24—C23—C37—O258.7 (4)C14—C15—C16—C11&#x (5)C22—C23—C37—O2&#x (3)C12—C11—C16—C150.2 (4)C24—C23—C37—C38&#x (3)C4—C11—C16—C15&#x (3)C22—C23—C37—C3860.2 (4)C4—C3—C17—O1&#x (4)O3—C2—N1—C6179.5 (3)C2—C3—C17—O196.6 (4)C3—C2—N1—C6&#x (4)C4—C3—C17—C1892.4 (4)C7—C6—N1—C2178.4 (3)C2—C3—C17—C18&#x (4)C5—C6—N1—C2&#x (4)O4—C22—C23—C24&#x (3)O4—C22—N2—C26176.7 (3)N2—C22—C23—C243.4 (4)C23—C22—N2—C26&#x (4)O4—C22—C23—C374.0 (4)C27—C26—N2—C22&#x (3)N2—C22—C23—C37&#x (2)C25—C26—N2—C220.0 (4)Hydrogen-bond geometry (Å, °) D—H···AD—HH···AD···AD—H···AN1—H2···O40.93 (3)1.88 (3)2.807 (3)171 (3)N2—H1···O30.96 (3)1.84 (3)2.795 (4)175 (3)Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: ).Cooper, K. M., Fray, J. M., Parry, J., Richardson, K. & Steele, J. (1992). J. Med. Chem.35, 3115&#x.
[]Enraf–Nonius (1994). CAD-4 Software Enraf–Nonius, Delft, The Netherlands.Gaudio, A. C., Korolkovas, A. & Takahata, Y. (1994). J. Pharm. Sci.83, 1110&#x.
[]Gordeev, M. F., Patel, D. V. & Gordon, E. M. (1996). J. Org. Chem.61, 924&#x.Harms, K. & Wocadlo, S. (1996). XCAD4 University of Marburg, Germany.North, A. C. T., Phillips, D. C. & Mathews, F. S. (1968). Acta Cryst. A24, 351&#x.Sheldrick, G. M. (2008). Acta Cryst. A64, 112&#x.
[]Spek, A. L. (2009). Acta Cryst. D65, 148&#x. []
[]Articles from Acta Crystallographica Section E: Structure Reports Online are provided here courtesy of International Union of Crystallography&}