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Acta Crystallogr Sect E Struct Rep Online. 2010 January 1; 66(Pt 1): o228.
Published online 2009 December 24. doi:  10.1107/S1600536809054087
PMCID: PMC2980191

3-Acetyl-6-chloro-4-phenyl­quinolin-2(1H)-one

Abstract

The title compound, C17H12ClNO2, crystallizes with two mol­ecules in the asymmetric unit. The main conformational difference between these two mol­ecules 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—H(...)O hydrogen bonds.

Related literature

For general background, see: Cooper et al. (1992 [triangle]); Gaudio et al. (1994 [triangle]); Gordeev et al. (1996 [triangle]).

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Object name is e-66-0o228-scheme1.jpg

Experimental

Crystal data

  • C17H12ClNO2
  • M r = 297.73
  • Monoclinic, An external file that holds a picture, illustration, etc.
Object name is e-66-0o228-efi1.jpg
  • a = 10.043 (5) Å
  • b = 18.663 (9) Å
  • c = 15.537 (7) Å
  • β = 91.811 (5)°
  • V = 2911 (2) Å3
  • Z = 8
  • Mo Kα radiation
  • μ = 0.27 mm−1
  • T = 293 K
  • 0.17 × 0.14 × 0.11 mm

Data collection

  • Nonius MACH-3 diffractometer
  • Absorption correction: ψ scan (North et al., 1968 [triangle]) T min = 0.955, T max = 0.967
  • 5771 measured reflections
  • 5104 independent reflections
  • 2567 reflections with I > 2σ(I)
  • R int = 0.015
  • 2 standard reflections every 60 min
  • intensity decay: none

Refinement

  • R[F 2 > 2σ(F 2)] = 0.041
  • wR(F 2) = 0.123
  • S = 1.00
  • 5104 reflections
  • 389 parameters
  • H atoms treated by a mixture of independent and constrained refinement
  • Δρmax = 0.22 e Å−3
  • Δρmin = −0.18 e Å−3

Data collection: CAD-4 EXPRESS (Enraf–Nonius, 1994 [triangle]); cell refinement: CAD-4 EXPRESS; data reduction: XCAD4 (Harms & Wocadlo, 1996 [triangle]); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 [triangle]); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 [triangle]); molecular graphics: PLATON (Spek, 2009 [triangle]); software used to prepare material for publication: SHELXL97.

Table 1
Hydrogen-bond geometry (Å, °)

Supplementary Material

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536809054087/bt5138sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536809054087/bt5138Isup2.hkl

Additional supplementary materials: crystallographic information; 3D view; checkCIF report

Acknowledgments

SN thanks the DST for the FIST programme and VV thanks the DST-India for funding through the Young Scientist-Fast Track Proposal.

supplementary crystallographic information

Comment

The molecular structure of the title compound is shown in Fig.1. There are two molecules in the asymmetric unit. The phenyl rings are twisted from the respective quinoline rings by 70.5 (1)° and 65.5 (1) Å.

The two molecules in the asymmetric unit interact through N—H···O bonds (Table 1).

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.224–226 °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 = 0.93–0.96 Å and Uiso = 1.2Ueq(C) for CH group, and 1.5Ueq for CH3 groups.

Figures

Fig. 1.
The molecular structure of the title compound, showing 50% probability displacement ellipsoids and the atom-numbering scheme.

Crystal data

C17H12ClNO2F(000) = 1232
Mr = 297.73Dx = 1.359 Mg m3
Monoclinic, P21/nMo Kα radiation, λ = 0.71069 Å
a = 10.043 (5) ÅCell parameters from 25 reflections
b = 18.663 (9) Åθ = 2–25°
c = 15.537 (7) ŵ = 0.27 mm1
β = 91.811 (5)°T = 293 K
V = 2911 (2) Å3Block, colourless
Z = 80.17 × 0.14 × 0.11 mm

Data collection

Nonius MACH-3 diffractometer2567 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tubeRint = 0.015
graphiteθmax = 25.0°, θmin = 2.2°
ω–2θ scansh = 0→11
Absorption correction: ψ scan (North et al., 1968)k = −1→22
Tmin = 0.955, Tmax = 0.967l = −18→18
5771 measured reflections2 standard reflections every 60 min
5104 independent reflections intensity decay: none

Refinement

Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.041Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.123H atoms treated by a mixture of independent and constrained refinement
S = 1.00w = 1/[σ2(Fo2) + (0.0478P)2 + 0.722P] where P = (Fo2 + 2Fc2)/3
5104 reflections(Δ/σ)max < 0.001
389 parametersΔρmax = 0.22 e Å3
0 restraintsΔρmin = −0.18 e Å3

Special 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 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)

xyzUiso*/Ueq
H10.316 (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*
C13−0.0410 (3)0.16005 (18)0.6726 (3)0.0794 (10)
H13−0.08750.12060.65070.095*
C14−0.0545 (3)0.17966 (19)0.7567 (2)0.0748 (10)
H14−0.11020.15370.79190.090*
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)
C18−0.0616 (4)0.4092 (2)0.5505 (3)0.1200 (16)
H18A−0.14580.41650.52090.180*
H18B−0.00900.45200.54710.180*
H18C−0.07610.39810.60980.180*
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)
H330.84030.5160−0.01360.111*
C340.8076 (3)0.6212 (3)−0.0001 (2)0.0867 (12)
H340.86270.6358−0.04370.104*
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)
O1−0.0477 (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)

U11U22U33U12U13U23
C20.060 (2)0.0565 (19)0.0479 (17)−0.0054 (15)0.0101 (15)0.0036 (15)
C30.0520 (16)0.0511 (17)0.0443 (15)−0.0056 (14)0.0084 (13)0.0003 (14)
C40.0523 (17)0.0437 (16)0.0479 (16)−0.0037 (13)0.0105 (13)−0.0030 (13)
C50.0505 (17)0.0454 (16)0.0501 (16)−0.0034 (14)0.0107 (13)−0.0038 (14)
C60.0542 (18)0.0470 (16)0.0501 (17)−0.0045 (14)0.0089 (14)−0.0023 (14)
C70.0529 (19)0.069 (2)0.070 (2)−0.0135 (16)0.0154 (16)0.0013 (17)
C80.0497 (18)0.085 (2)0.076 (2)−0.0036 (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)−0.0007 (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)−0.0150 (18)−0.0003 (16)0.0054 (17)
C130.062 (2)0.071 (2)0.104 (3)−0.0253 (18)−0.008 (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)−0.0048 (16)0.0233 (17)0.0036 (16)
C170.061 (2)0.070 (2)0.0540 (19)−0.0131 (18)0.0008 (16)0.0155 (17)
C180.062 (2)0.148 (4)0.150 (4)0.021 (2)0.007 (2)−0.056 (3)
O30.0667 (13)0.0785 (15)0.0636 (13)−0.0070 (11)0.0064 (11)0.0250 (12)
C220.065 (2)0.0456 (17)0.0517 (19)−0.0083 (15)0.0096 (15)0.0025 (14)
C230.0564 (18)0.0438 (16)0.0529 (17)−0.0061 (14)0.0064 (14)0.0009 (14)
C240.0512 (17)0.0461 (17)0.0520 (17)−0.0047 (13)0.0084 (14)−0.0015 (14)
C250.0525 (17)0.0527 (17)0.0503 (17)−0.0030 (14)0.0112 (14)0.0027 (14)
C260.0569 (18)0.0448 (16)0.0520 (17)−0.0033 (14)0.0137 (14)0.0016 (14)
C270.0556 (19)0.066 (2)0.066 (2)−0.0048 (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)−0.0009 (16)0.0145 (15)0.0191 (17)
C310.0457 (16)0.0646 (19)0.0481 (16)−0.0035 (15)0.0068 (13)0.0030 (15)
C320.071 (2)0.077 (2)0.076 (2)−0.0058 (18)0.0191 (19)−0.0045 (19)
C330.083 (3)0.122 (3)0.074 (2)0.002 (2)0.034 (2)−0.012 (2)
C340.057 (2)0.139 (4)0.064 (2)−0.012 (2)0.0140 (17)0.021 (2)
C350.061 (2)0.093 (3)0.079 (2)−0.0124 (19)0.0078 (18)0.029 (2)
C360.0572 (19)0.070 (2)0.068 (2)−0.0015 (16)0.0098 (16)0.0126 (17)
C370.0568 (19)0.058 (2)0.0544 (18)−0.0079 (16)0.0008 (14)0.0053 (15)
C380.072 (2)0.064 (2)0.138 (3)0.0064 (19)−0.001 (2)0.011 (2)
O40.0733 (14)0.0715 (14)0.0584 (13)−0.0113 (11)0.0020 (11)0.0184 (11)
N10.0574 (16)0.0558 (16)0.0566 (16)−0.0119 (13)0.0096 (13)0.0084 (13)
N20.0586 (17)0.0535 (15)0.0546 (15)−0.0056 (13)0.0168 (13)0.0062 (12)
O10.099 (2)0.107 (2)0.130 (2)−0.0089 (17)−0.0444 (17)−0.0113 (18)
O20.0640 (14)0.0715 (15)0.1075 (18)−0.0165 (12)−0.0092 (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—H270.9300
C7—H70.9300C28—C291.390 (4)
C8—C91.385 (4)C28—H280.9300
C8—H80.9300C29—C301.371 (4)
C9—C101.367 (4)C29—Cl21.735 (3)
C9—Cl11.733 (3)C30—H300.9300
C10—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—H320.9300
C12—H120.9300C33—C341.368 (5)
C13—C141.368 (5)C33—H330.9300
C13—H130.9300C34—C351.358 (5)
C14—C151.364 (4)C34—H340.9300
C14—H140.9300C35—C361.384 (4)
C15—C161.370 (4)C35—H350.9300
C15—H150.9300C36—H360.9300
C16—H160.9300C37—O21.206 (3)
C17—O11.190 (3)C37—C381.495 (4)
C17—C181.459 (5)C38—H38A0.9600
C18—H18A0.9600C38—H38B0.9600
C18—H18B0.9600C38—H38C0.9600
C18—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—H27119.9
C7—C6—C5120.5 (3)C26—C27—H27119.9
C8—C7—C6120.5 (3)C27—C28—C29119.1 (3)
C8—C7—H7119.8C27—C28—H28120.5
C6—C7—H7119.8C29—C28—H28120.5
C7—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—H30119.7
C8—C9—Cl1119.8 (2)C25—C30—H30119.7
C9—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—H32119.7
C16—C11—C4119.8 (2)C33—C32—H32119.7
C11—C12—C13120.2 (3)C34—C33—C32120.1 (3)
C11—C12—H12119.9C34—C33—H33120.0
C13—C12—H12119.9C32—C33—H33120.0
C14—C13—C12120.3 (3)C35—C34—C33120.1 (3)
C14—C13—H13119.8C35—C34—H34120.0
C12—C13—H13119.8C33—C34—H34120.0
C15—C14—C13119.8 (3)C34—C35—C36120.2 (3)
C15—C14—H14120.1C34—C35—H35119.9
C13—C14—H14120.1C36—C35—H35119.9
C14—C15—C16120.2 (3)C31—C36—C35120.9 (3)
C14—C15—H15119.9C31—C36—H36119.6
C16—C15—H15119.9C35—C36—H36119.6
C15—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—H38A109.5
O1—C17—C3120.7 (3)C37—C38—H38B109.5
C18—C17—C3117.7 (3)H38A—C38—H38B109.5
C17—C18—H18A109.5C37—C38—H38C109.5
C17—C18—H18B109.5H38A—C38—H38C109.5
H18A—C18—H18B109.5H38B—C38—H38C109.5
C17—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—C4−178.0 (3)C22—C23—C24—C25−0.1 (4)
N1—C2—C3—C42.2 (4)C37—C23—C24—C25179.2 (3)
O3—C2—C3—C17−1.9 (4)C22—C23—C24—C31−176.7 (2)
N1—C2—C3—C17178.2 (3)C37—C23—C24—C312.6 (4)
C2—C3—C4—C5−2.5 (4)C23—C24—C25—C30178.7 (3)
C17—C3—C4—C5−178.2 (3)C31—C24—C25—C30−4.6 (4)
C2—C3—C4—C11177.0 (2)C23—C24—C25—C26−3.3 (4)
C17—C3—C4—C111.3 (4)C31—C24—C25—C26173.4 (2)
C3—C4—C5—C10−177.3 (3)C30—C25—C26—N2−178.5 (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—C6−178.3 (2)C24—C25—C26—C27−176.8 (3)
C10—C5—C6—N1178.9 (2)N2—C26—C27—C28177.7 (3)
C4—C5—C6—N10.2 (4)C25—C26—C27—C28−2.0 (4)
C10—C5—C6—C7−0.1 (4)C26—C27—C28—C290.4 (5)
C4—C5—C6—C7−178.7 (2)C27—C28—C29—C301.9 (5)
N1—C6—C7—C8−179.2 (3)C27—C28—C29—Cl2180.0 (2)
C5—C6—C7—C8−0.3 (4)C28—C29—C30—C25−2.7 (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—C5−0.3 (5)C23—C24—C31—C36−117.9 (3)
Cl1—C9—C10—C5−180.0 (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—C32−113.7 (3)
C3—C4—C11—C1270.2 (4)C36—C31—C32—C330.4 (5)
C5—C4—C11—C12−110.3 (3)C24—C31—C32—C33179.6 (3)
C3—C4—C11—C16−110.8 (3)C31—C32—C33—C34−0.5 (5)
C5—C4—C11—C1668.7 (3)C32—C33—C34—C350.5 (6)
C16—C11—C12—C130.3 (4)C33—C34—C35—C36−0.6 (5)
C4—C11—C12—C13179.3 (3)C32—C31—C36—C35−0.5 (4)
C11—C12—C13—C14−0.3 (5)C24—C31—C36—C35−179.6 (3)
C12—C13—C14—C15−0.2 (5)C34—C35—C36—C310.5 (5)
C13—C14—C15—C160.6 (5)C24—C23—C37—O258.7 (4)
C14—C15—C16—C11−0.6 (5)C22—C23—C37—O2−122.0 (3)
C12—C11—C16—C150.2 (4)C24—C23—C37—C38−119.2 (3)
C4—C11—C16—C15−178.9 (3)C22—C23—C37—C3860.2 (4)
C4—C3—C17—O1−87.4 (4)O3—C2—N1—C6179.5 (3)
C2—C3—C17—O196.6 (4)C3—C2—N1—C6−0.7 (4)
C4—C3—C17—C1892.4 (4)C7—C6—N1—C2178.4 (3)
C2—C3—C17—C18−83.5 (4)C5—C6—N1—C2−0.5 (4)
O4—C22—C23—C24−176.6 (3)O4—C22—N2—C26176.7 (3)
N2—C22—C23—C243.4 (4)C23—C22—N2—C26−3.3 (4)
O4—C22—C23—C374.0 (4)C27—C26—N2—C22−179.8 (3)
N2—C22—C23—C37−176.0 (2)C25—C26—N2—C220.0 (4)

Hydrogen-bond geometry (Å, °)

D—H···AD—HH···AD···AD—H···A
N1—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)

Footnotes

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: BT5138).

References

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