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Acta Crystallogr Sect E Struct Rep Online. 2010 April 1; 66(Pt 4): o830.
Published online 2010 March 13. doi:  10.1107/S1600536810009098
PMCID: PMC2983761

5-Fluoro-N′-[(E)-4-methoxy­benzyl­idene]-3-phenyl-1H-indole-2-carbohydrazide

Abstract

In the title mol­ecule, C23H18FN3O2, the mean plane of the indole system forms dihedral angles of 44.23 (8) and 14.54 (7)°, respectively, with the phenyl and benzene rings. In the crystal, inter­molecular N—H(...)O hydrogen bonds link mol­ecules into two-layer ribbons extended along the b axis. The crystal packing also exhibits weak inter­molecular C—H(...)O, C—H(...)F and C—H(...)π inter­actions.

Related literature

For the synthesis and characterization of related indole derivatives, see: Akkurt et al. (2009 [triangle]); Güzel et al. (2006 [triangle]); Kaynak et al. (2005 [triangle]). For typical values of bond lengths in organic compounds, see: Allen et al. (1987 [triangle]).

An external file that holds a picture, illustration, etc.
Object name is e-66-0o830-scheme1.jpg

Experimental

Crystal data

  • C23H18FN3O2
  • M r = 387.40
  • Monoclinic, An external file that holds a picture, illustration, etc.
Object name is e-66-0o830-efi1.jpg
  • a = 19.5709 (11) Å
  • b = 5.1546 (2) Å
  • c = 24.3584 (14) Å
  • β = 127.686 (3)°
  • V = 1944.63 (19) Å3
  • Z = 4
  • Mo Kα radiation
  • μ = 0.09 mm−1
  • T = 296 K
  • 0.60 × 0.38 × 0.07 mm

Data collection

  • Stoe IPDS2 diffractometer
  • Absorption correction: integration (X-RED32; Stoe & Cie, 2002 [triangle]) T min = 0.958, T max = 0.994
  • 23274 measured reflections
  • 4053 independent reflections
  • 2900 reflections with I > 2σ(I)
  • R int = 0.038

Refinement

  • R[F 2 > 2σ(F 2)] = 0.038
  • wR(F 2) = 0.096
  • S = 1.03
  • 4053 reflections
  • 264 parameters
  • H-atom parameters constrained
  • Δρmax = 0.12 e Å−3
  • Δρmin = −0.13 e Å−3

Data collection: X-AREA (Stoe & Cie, 2002 [triangle]); cell refinement: X-AREA; data reduction: X-RED32 (Stoe & Cie, 2002 [triangle]); program(s) used to solve structure: SIR97 (Altomare et al., 1999 [triangle]); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 [triangle]); molecular graphics: ORTEP-3 (Farrugia, 1997 [triangle]); software used to prepare material for publication: WinGX (Farrugia, 1999 [triangle]).

Table 1
Hydrogen-bond geometry (Å, °)

Supplementary Material

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536810009098/cv2701sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536810009098/cv2701Isup2.hkl

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

Acknowledgments

The authors acknowledge the Faculty of Arts and Sciences, Ondokuz Mayıs University, Turkey, for the use of the Stoe IPDS2 diffractometer (purchased under grant F.279 of the University Research Fund). This work was supported in part by the Research Fund of İstanbul University (Project T-2827).

supplementary crystallographic information

Comment

In the framework of our ongoing project directed towards the design, synthesis and characterization of bioactive indole derivatives (Akkurt et al., 2009; Güzel et al., 2006; Kaynak et al., 2005), we report here the synthesis and crystal structure of the title compound.

In the title molecule (Fig. 1), bond lengths and bond angles are all within expected values (Allen et al., 1987). The nine-membered indole ring [a maximum deviation from the mean plane of 0.039 (2) Å for C6] makes dihedral angles of 44.23 (8)° and 14.54 (7)°, respectively, with the phenyl ring (C9–C14) and benzene ring (C17–C22). The (C9–C14) and (C17–C22) rings form a dihedral angle of 36.87 (9)°.

In the crystal structure, intermolecular N—H···O hydrogen bonds link molecules into two-layer ribbons extended along b axis. The crystal packing exhibits also weak intermolecular C—H···O, C—H···F and C—H···π interactions (Table 1).

Experimental

A mixture of 5-fluoro-3-phenyl-1H-indole-2-carbohydrazide (0.005 mol), 4-methoxy benzaldehyde (0.006 mol) and 15 ml of absolute ethanol was heated on a water bath for 4 h. The crude product obtained on cooling was filtered and purified by recrystallization from ethanol/chloroform (1/1). [Yield: 93.8 %, m.p.: 493-493 K]. IR (KBr) ν = 3247 (N—H), 1635 (C=O), 1622 (C=N) cm-1; 1H-NMR (DMSO-d6, 500 MHz) δ = 3.78 (3H, s, 4-OCH3), 6.99 (2H, d*, J=6.8 Hz, H3,H5-benzylidene), 7.14 (1H, t*, J=8.8 Hz, H6-indole), 7.31-7.52 (7H, m, H4, H7, 3-C6H5-indole), 7.62 (2H, d*, J=5.9 Hz, H2, H6-benzylidene), 8.02 (1H, s, N=CH), 11.23 (1H, s, CONH), 12.02 (1H, s, NH-indole) ppm ( * = broad). Analysis calculated for C23H18FN3O2 : C 71.31, H 4.68, N 10.85 %. Found : C 71.22, H 3.94, N 10.82 %.

Refinement

H atoms were placed in idealized positions with N—H = 0.86 Å and C—H = 0.93 - 0.96 Å, and constrained to ride on their parent atoms with Uiso(H) = 1.2 or 1.5Ueq(C, N).

Figures

Fig. 1.
View of the title molecule showing the atomic numbering and 50% probability displacement ellipsoids.

Crystal data

C23H18FN3O2F(000) = 808
Mr = 387.40Dx = 1.323 Mg m3
Monoclinic, P21/cMo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybcCell parameters from 8633 reflections
a = 19.5709 (11) Åθ = 1.8–27.3°
b = 5.1546 (2) ŵ = 0.09 mm1
c = 24.3584 (14) ÅT = 296 K
β = 127.686 (3)°Plate, colourless
V = 1944.63 (19) Å30.60 × 0.38 × 0.07 mm
Z = 4

Data collection

Stoe IPDS2 diffractometer4053 independent reflections
Radiation source: sealed X-ray tube, 12 x 0.4 mm long-fine focus2900 reflections with I > 2σ(I)
plane graphiteRint = 0.038
Detector resolution: 6.67 pixels mm-1θmax = 26.5°, θmin = 1.3°
ω scansh = −24→24
Absorption correction: integration (X-RED32; Stoe & Cie, 2002)k = −6→6
Tmin = 0.958, Tmax = 0.994l = −30→30
23274 measured reflections

Refinement

Refinement on F2Secondary atom site location: difference Fourier map
Least-squares matrix: fullHydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.038H-atom parameters constrained
wR(F2) = 0.096w = 1/[σ2(Fo2) + (0.0532P)2] where P = (Fo2 + 2Fc2)/3
S = 1.03(Δ/σ)max < 0.001
4053 reflectionsΔρmax = 0.12 e Å3
264 parametersΔρmin = −0.12 e Å3
0 restraintsExtinction correction: SHELXL97 (Sheldrick, 2008), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
Primary atom site location: structure-invariant direct methodsExtinction coefficient: 0.0123 (12)

Special details

Geometry. Bond distances, angles etc. have been calculated using the rounded fractional coordinates. All su's are estimated from the variances of the (full) variance-covariance matrix. The cell esds are taken into account in the estimation of distances, angles and torsion angles
Refinement. Refinement on F2 for ALL reflections except those flagged by the user for potential systematic errors. Weighted R-factors wR and all goodnesses of fit S are based on F2, conventional R-factors R are based on F, with F set to zero for negative F2. The observed criterion of F2 > σ(F2) is used only for calculating -R-factor-obs 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
F10.96473 (6)0.3955 (3)0.67120 (6)0.1153 (5)
O10.46022 (6)0.08712 (18)0.41796 (5)0.0624 (3)
O2−0.00747 (7)0.7292 (3)0.05087 (6)0.0898 (4)
N10.62743 (7)0.1715 (2)0.53758 (5)0.0565 (4)
N20.45250 (7)0.5105 (2)0.38898 (6)0.0532 (4)
N30.36665 (7)0.4917 (2)0.33221 (6)0.0553 (4)
C10.71455 (9)0.2113 (3)0.57970 (7)0.0560 (4)
C20.77885 (11)0.0917 (3)0.64212 (8)0.0747 (6)
C30.86269 (11)0.1589 (4)0.67208 (8)0.0867 (7)
C40.87981 (9)0.3381 (4)0.63954 (8)0.0778 (6)
C50.81907 (9)0.4567 (3)0.57871 (7)0.0637 (5)
C60.73246 (8)0.3953 (3)0.54742 (6)0.0505 (4)
C70.65172 (8)0.4668 (2)0.48304 (6)0.0464 (4)
C80.58921 (8)0.3256 (2)0.47996 (6)0.0480 (4)
C90.64238 (8)0.6238 (2)0.42835 (6)0.0465 (4)
C100.69245 (9)0.8454 (2)0.44513 (8)0.0567 (4)
C110.68968 (10)0.9792 (3)0.39482 (10)0.0702 (6)
C120.63650 (11)0.8975 (3)0.32699 (10)0.0775 (7)
C130.58566 (10)0.6816 (3)0.30908 (8)0.0686 (5)
C140.58882 (8)0.5452 (3)0.35932 (7)0.0544 (4)
C150.49563 (8)0.2983 (3)0.42673 (6)0.0493 (4)
C160.33397 (9)0.6934 (3)0.29425 (7)0.0565 (5)
C170.24446 (8)0.6999 (3)0.23225 (7)0.0546 (4)
C180.21612 (10)0.8892 (3)0.18233 (9)0.0710 (6)
C190.13225 (11)0.8934 (3)0.12238 (9)0.0781 (6)
C200.07431 (9)0.7099 (3)0.11180 (8)0.0672 (5)
C210.10054 (10)0.5219 (3)0.16103 (8)0.0712 (5)
C220.18461 (9)0.5177 (3)0.22030 (8)0.0665 (5)
C23−0.06706 (11)0.5297 (4)0.03519 (11)0.0994 (8)
H10.600700.066200.545900.0680*
H20.76550−0.028900.662700.0900*
H2A0.478400.657900.400200.0640*
H30.907700.084600.714000.1040*
H50.833900.573600.558500.0760*
H100.728100.903700.490800.0680*
H110.724001.125500.406800.0840*
H120.634900.988200.293200.0930*
H130.549100.627400.263100.0820*
H140.554600.398400.346800.0650*
H160.368200.840100.306500.0680*
H180.254501.016300.189400.0850*
H190.114801.020400.089100.0940*
H210.061500.397900.154200.0850*
H220.201800.389400.253200.0800*
H23A−0.044000.365000.035400.1490*
H23B−0.120700.56020−0.009800.1490*
H23C−0.076700.529200.069400.1490*

Atomic displacement parameters (Å2)

U11U22U33U12U13U23
F10.0444 (5)0.1659 (11)0.0877 (7)0.0028 (6)0.0158 (5)−0.0115 (7)
O10.0607 (6)0.0602 (6)0.0590 (6)−0.0204 (5)0.0328 (5)−0.0045 (4)
O20.0559 (7)0.1070 (9)0.0738 (7)0.0105 (6)0.0229 (6)0.0101 (7)
N10.0587 (7)0.0636 (7)0.0512 (6)−0.0052 (5)0.0357 (6)0.0048 (5)
N20.0418 (6)0.0510 (6)0.0596 (7)−0.0069 (5)0.0273 (5)−0.0058 (5)
N30.0421 (6)0.0623 (7)0.0557 (6)−0.0046 (5)0.0270 (5)−0.0076 (5)
C10.0562 (8)0.0663 (8)0.0436 (7)0.0036 (7)0.0296 (7)−0.0009 (6)
C20.0781 (11)0.0916 (11)0.0505 (8)0.0176 (9)0.0373 (8)0.0118 (8)
C30.0666 (11)0.1203 (15)0.0461 (8)0.0268 (10)0.0205 (8)0.0064 (9)
C40.0457 (8)0.1054 (13)0.0574 (9)0.0035 (8)0.0187 (8)−0.0120 (9)
C50.0477 (8)0.0754 (9)0.0565 (8)−0.0037 (7)0.0260 (7)−0.0089 (7)
C60.0462 (7)0.0571 (7)0.0434 (7)−0.0029 (6)0.0249 (6)−0.0067 (6)
C70.0442 (7)0.0484 (7)0.0450 (7)−0.0053 (5)0.0264 (6)−0.0050 (5)
C80.0488 (7)0.0504 (7)0.0446 (7)−0.0046 (6)0.0285 (6)−0.0021 (6)
C90.0426 (6)0.0467 (6)0.0531 (7)0.0014 (5)0.0307 (6)0.0012 (5)
C100.0521 (7)0.0503 (7)0.0696 (9)−0.0029 (6)0.0382 (7)−0.0014 (6)
C110.0626 (9)0.0576 (8)0.0977 (13)0.0018 (7)0.0528 (10)0.0177 (8)
C120.0767 (11)0.0853 (11)0.0863 (12)0.0158 (9)0.0580 (10)0.0338 (10)
C130.0667 (9)0.0824 (10)0.0571 (8)0.0094 (8)0.0380 (8)0.0131 (8)
C140.0503 (7)0.0584 (8)0.0519 (8)0.0003 (6)0.0299 (7)0.0038 (6)
C150.0494 (7)0.0548 (7)0.0472 (7)−0.0108 (6)0.0314 (6)−0.0074 (6)
C160.0528 (8)0.0566 (8)0.0606 (8)−0.0048 (6)0.0349 (7)−0.0101 (7)
C170.0506 (7)0.0562 (7)0.0556 (8)0.0026 (6)0.0318 (7)−0.0065 (6)
C180.0625 (9)0.0616 (9)0.0798 (11)−0.0024 (7)0.0388 (9)0.0014 (8)
C190.0693 (10)0.0719 (10)0.0750 (10)0.0081 (8)0.0349 (9)0.0150 (8)
C200.0513 (8)0.0749 (10)0.0608 (9)0.0086 (7)0.0268 (7)−0.0027 (8)
C210.0516 (8)0.0766 (10)0.0718 (10)−0.0047 (7)0.0308 (8)0.0023 (8)
C220.0538 (8)0.0694 (9)0.0637 (9)−0.0012 (7)0.0295 (7)0.0068 (7)
C230.0472 (9)0.1322 (17)0.0881 (13)−0.0010 (10)0.0257 (9)−0.0051 (12)

Geometric parameters (Å, °)

F1—C41.370 (2)C12—C131.374 (3)
O1—C151.2369 (19)C13—C141.380 (2)
O2—C201.367 (2)C16—C171.455 (2)
O2—C231.421 (3)C17—C221.386 (3)
N1—C11.365 (2)C17—C181.383 (2)
N1—C81.3699 (15)C18—C191.377 (3)
N2—N31.3798 (19)C19—C201.375 (3)
N2—C151.3437 (18)C20—C211.374 (2)
N3—C161.2735 (18)C21—C221.374 (3)
N1—H10.8600C2—H20.9300
N2—H2A0.8600C3—H30.9300
C1—C21.391 (2)C5—H50.9300
C1—C61.406 (2)C10—H100.9300
C2—C31.371 (3)C11—H110.9300
C3—C41.385 (3)C12—H120.9300
C4—C51.352 (2)C13—H130.9300
C5—C61.405 (3)C14—H140.9300
C6—C71.4360 (19)C16—H160.9300
C7—C81.386 (2)C18—H180.9300
C7—C91.4715 (18)C19—H190.9300
C8—C151.467 (2)C21—H210.9300
C9—C141.3911 (18)C22—H220.9300
C9—C101.3937 (19)C23—H23A0.9600
C10—C111.378 (3)C23—H23B0.9600
C11—C121.374 (3)C23—H23C0.9600
F1···H3i2.5400C14···H11iii3.0500
F1···H21ii2.6500C15···H1iv3.0100
O1···N12.7803 (16)C15···H142.8500
O1···N2iii3.0373 (14)C16···H12ix2.7600
O1···N32.7182 (15)C17···H12ix2.9900
O1···C16iii3.1939 (18)C21···H23C2.7500
O1···N1iv2.8573 (19)C21···H23A2.7300
O1···H2Aiii2.3200C23···H212.5100
O1···H16iii2.5000C23···H5x3.1000
O1···H12.6100H1···O12.6100
O1···H1iv2.0300H1···O1iv2.0300
O2···H23Av2.8700H1···C15iv3.0100
N1···O12.7803 (16)H2···H22iv2.5400
N1···O1iv2.8573 (19)H2A···O1vi2.3200
N2···O1vi3.0373 (14)H2A···C72.8600
N2···C93.273 (2)H2A···C92.8500
N2···C143.167 (2)H2A···C142.9400
N3···O12.7182 (15)H2A···H162.1700
N2···H142.8100H3···F1xi2.5400
N3···H222.6100H5···C102.8100
C1···C10iii3.572 (2)H5···H102.3900
C2···C22vii3.587 (2)H5···C23viii3.1000
C2···C16vii3.562 (3)H5···H23Cviii2.6000
C2···C17vii3.526 (3)H10···C1vi2.8200
C5···C103.299 (2)H10···C52.9000
C6···C10iii3.5313 (19)H10···C62.9400
C7···C10iii3.5564 (17)H10···C6vi2.8600
C9···N23.273 (2)H10···H52.3900
C10···C7vi3.5564 (17)H11···C14vi3.0500
C10···C6vi3.5313 (19)H11···H23Bviii2.5900
C10···C53.299 (2)H12···C16xii2.7600
C10···C1vi3.572 (2)H12···C17xii2.9900
C11···C14vi3.327 (2)H13···H14xii2.5700
C14···N23.167 (2)H14···N22.8100
C14···C153.362 (2)H14···C82.9000
C14···C11iii3.327 (2)H14···C11iii3.0400
C15···C143.362 (2)H14···C152.8500
C16···C2vii3.562 (3)H14···H13ix2.5700
C16···O1vi3.1939 (18)H16···O1vi2.5000
C17···C2vii3.526 (3)H16···H2A2.1700
C18···C22vi3.525 (2)H16···H182.4800
C19···C21vi3.533 (2)H18···H162.4800
C21···C19iii3.533 (2)H21···C232.5100
C22···C18iii3.525 (2)H21···H23A2.3200
C22···C2vii3.587 (2)H21···H23C2.2800
C1···H10iii2.8200H21···F1xiii2.6500
C4···H23Cii3.0000H22···N32.6100
C5···H102.9000H22···H2iv2.5400
C6···H10iii2.8600H23A···C212.7300
C6···H102.9400H23A···H212.3200
C7···H2A2.8600H23A···O2v2.8700
C8···H142.9000H23B···C11x2.9400
C9···H2A2.8500H23B···H11x2.5900
C10···H52.8100H23C···C212.7500
C11···H23Bviii2.9400H23C···H212.2800
C11···H14vi3.0400H23C···C4xiii3.0000
C14···H2A2.9400H23C···H5x2.6000
C20—O2—C23117.57 (15)C16—C17—C18120.67 (16)
C1—N1—C8109.37 (13)C17—C18—C19121.38 (18)
N3—N2—C15119.95 (11)C18—C19—C20119.99 (16)
N2—N3—C16115.70 (13)O2—C20—C19115.94 (15)
C8—N1—H1125.00C19—C20—C21119.76 (17)
C1—N1—H1125.00O2—C20—C21124.30 (17)
N3—N2—H2A120.00C20—C21—C22119.78 (18)
C15—N2—H2A120.00C17—C22—C21121.69 (15)
N1—C1—C2129.38 (17)C1—C2—H2121.00
N1—C1—C6107.75 (12)C3—C2—H2121.00
C2—C1—C6122.80 (18)C2—C3—H3120.00
C1—C2—C3117.27 (18)C4—C3—H3120.00
C2—C3—C4119.55 (16)C4—C5—H5122.00
F1—C4—C5118.06 (18)C6—C5—H5121.00
C3—C4—C5124.78 (19)C9—C10—H10120.00
F1—C4—C3117.16 (16)C11—C10—H10120.00
C4—C5—C6116.96 (16)C10—C11—H11120.00
C5—C6—C7133.76 (14)C12—C11—H11120.00
C1—C6—C5118.62 (13)C11—C12—H12120.00
C1—C6—C7107.44 (14)C13—C12—H12120.00
C8—C7—C9128.53 (12)C12—C13—H13120.00
C6—C7—C9125.07 (15)C14—C13—H13120.00
C6—C7—C8105.66 (11)C9—C14—H14120.00
N1—C8—C15117.04 (13)C13—C14—H14119.00
C7—C8—C15133.02 (11)N3—C16—H16119.00
N1—C8—C7109.76 (13)C17—C16—H16119.00
C7—C9—C10120.62 (11)C17—C18—H18119.00
C7—C9—C14121.26 (12)C19—C18—H18119.00
C10—C9—C14117.93 (13)C18—C19—H19120.00
C9—C10—C11120.73 (14)C20—C19—H19120.00
C10—C11—C12120.33 (17)C20—C21—H21120.00
C11—C12—C13119.95 (18)C22—C21—H21120.00
C12—C13—C14120.00 (15)C17—C22—H22119.00
C9—C14—C13121.05 (15)C21—C22—H22119.00
N2—C15—C8116.70 (13)O2—C23—H23A109.00
O1—C15—N2123.16 (14)O2—C23—H23B109.00
O1—C15—C8120.14 (13)O2—C23—H23C109.00
N3—C16—C17121.61 (15)H23A—C23—H23B109.00
C16—C17—C22121.94 (14)H23A—C23—H23C110.00
C18—C17—C22117.39 (15)H23B—C23—H23C109.00
C23—O2—C20—C19174.44 (18)C6—C7—C8—N1−1.05 (15)
C23—O2—C20—C21−5.2 (3)C9—C7—C8—C15−5.4 (2)
C1—N1—C8—C15176.77 (13)C6—C7—C9—C10−43.7 (2)
C1—N1—C8—C71.04 (16)C8—C7—C9—C14−37.6 (2)
C8—N1—C1—C2−177.67 (17)C9—C7—C8—N1169.40 (13)
C8—N1—C1—C6−0.58 (17)N1—C8—C15—N2150.12 (13)
N3—N2—C15—O1−7.9 (2)N1—C8—C15—O1−30.4 (2)
C15—N2—N3—C16−171.16 (16)C7—C8—C15—N2−35.4 (2)
N3—N2—C15—C8171.54 (14)C7—C8—C15—O1144.08 (15)
N2—N3—C16—C17179.22 (15)C10—C9—C14—C130.3 (3)
N1—C1—C2—C3176.36 (17)C7—C9—C10—C11173.95 (17)
N1—C1—C6—C7−0.07 (18)C14—C9—C10—C11−1.0 (3)
N1—C1—C6—C5−175.83 (14)C7—C9—C14—C13−174.61 (17)
C2—C1—C6—C7177.25 (15)C9—C10—C11—C120.8 (3)
C6—C1—C2—C3−0.3 (3)C10—C11—C12—C130.1 (3)
C2—C1—C6—C51.5 (2)C11—C12—C13—C14−0.8 (3)
C1—C2—C3—C4−0.4 (3)C12—C13—C14—C90.6 (3)
C2—C3—C4—F1−179.10 (17)N3—C16—C17—C2216.5 (3)
C2—C3—C4—C50.0 (3)N3—C16—C17—C18−162.92 (18)
C3—C4—C5—C61.2 (3)C16—C17—C22—C21−178.75 (17)
F1—C4—C5—C6−179.77 (15)C18—C17—C22—C210.7 (3)
C4—C5—C6—C1−1.8 (2)C16—C17—C18—C19178.02 (18)
C4—C5—C6—C7−176.23 (17)C22—C17—C18—C19−1.4 (3)
C5—C6—C7—C8175.53 (17)C17—C18—C19—C201.3 (3)
C5—C6—C7—C94.7 (3)C18—C19—C20—C21−0.4 (3)
C1—C6—C7—C9−170.19 (12)C18—C19—C20—O2179.97 (18)
C1—C6—C7—C80.68 (16)O2—C20—C21—C22179.27 (18)
C6—C7—C9—C14131.12 (17)C19—C20—C21—C22−0.4 (3)
C6—C7—C8—C15−175.85 (15)C20—C21—C22—C170.2 (3)
C8—C7—C9—C10147.59 (16)

Symmetry codes: (i) −x+2, y+1/2, −z+3/2; (ii) x+1, −y+1/2, z+1/2; (iii) x, y−1, z; (iv) −x+1, −y, −z+1; (v) −x, −y+1, −z; (vi) x, y+1, z; (vii) −x+1, −y+1, −z+1; (viii) x+1, −y+3/2, z+1/2; (ix) −x+1, y−1/2, −z+1/2; (x) x−1, −y+3/2, z−1/2; (xi) −x+2, y−1/2, −z+3/2; (xii) −x+1, y+1/2, −z+1/2; (xiii) x−1, −y+1/2, z−1/2.

Hydrogen-bond geometry (Å, °)

Cg1 is the centroid of the N1/C1/C6–C8 ring.
D—H···AD—HH···AD···AD—H···A
N1—H1···O1iv0.862.032.8573 (19)162
N2—H2A···O1vi0.862.323.0373 (14)141
C3—H3···F1xi0.932.543.473 (2)177
C16—H16···O1vi0.932.503.1939 (18)131
C10—H10···Cg1vi0.932.853.3736 (17)117

Symmetry codes: (iv) −x+1, −y, −z+1; (vi) x, y+1, z; (xi) −x+2, y−1/2, −z+3/2.

Footnotes

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: CV2701).

References

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