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Acta Crystallogr Sect E Struct Rep Online. 2008 February 1; 64(Pt 2): o474.
Published online 2008 January 18. doi:  10.1107/S1600536808001359
PMCID: PMC2960319

5-(4-Fluoro­phen­yl)-2-furylmethyl N-(2,6-difluoro­benzo­yl)carbamate

Abstract

The title compound, C19H12F3NO4, was synthesized by the reaction of 5-(4-fluoro­phen­yl)-2-furan­methanol and 2,6-difluoro­benzoyl­isocyanate. The seven atoms of the fluorophenyl group are disordered over two positions with site occupancy factors ca 0.6 and 0.4. The dihedral angle between the furan and fluorophenyl rings is 1.58°. In the crystal structure, the mol­ecules are linked via inter­molecular N—H(...)O hydrogen bonds to form chains.

Related literature

For related literature, see: Grosscurt & Tipker (1980 [triangle]); Grugier et al. (2000 [triangle]); Li et al. (2007 [triangle]); Yang et al. (1997 [triangle], 1998 [triangle], 2002 [triangle]).

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Object name is e-64-0o474-scheme1.jpg

Experimental

Crystal data

  • C19H12F3NO4
  • M r = 375.30
  • Monoclinic, An external file that holds a picture, illustration, etc.
Object name is e-64-0o474-efi1.jpg
  • a = 7.5594 (11) Å
  • b = 12.9878 (19) Å
  • c = 17.332 (2) Å
  • β = 94.662 (2)°
  • V = 1696.0 (4) Å3
  • Z = 4
  • Mo Kα radiation
  • μ = 0.13 mm−1
  • T = 294 (2) K
  • 0.26 × 0.20 × 0.14 mm

Data collection

  • Bruker SMART CCD area-detector diffractometer
  • Absorption correction: multi-scan (SADABS; Sheldrick, 1996 [triangle]) T min = 0.968, T max = 0.983
  • 9559 measured reflections
  • 3453 independent reflections
  • 2305 reflections with I > 2σ(I)
  • R int = 0.026

Refinement

  • R[F 2 > 2σ(F 2)] = 0.038
  • wR(F 2) = 0.103
  • S = 1.00
  • 3453 reflections
  • 288 parameters
  • 99 restraints
  • H-atom parameters constrained
  • Δρmax = 0.16 e Å−3
  • Δρmin = −0.17 e Å−3

Data collection: SMART (Bruker, 1999 [triangle]); cell refinement: SAINT (Bruker, 1999 [triangle]); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 [triangle]); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 [triangle]); molecular graphics: SHELXTL (Sheldrick, 2008 [triangle]); software used to prepare material for publication: SHELXTL.

Table 1
Hydrogen-bond geometry (Å, °)

Supplementary Material

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536808001359/sg2221sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536808001359/sg2221Isup2.hkl

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

Acknowledgments

This work was supported by the National Basic Research Program of China (2003CB114400), the National Natural Science Foundation of China (20672138) and the National High Technology Research and Development Program of China (2006AA10A201). We acknowledge Dr Wenbin Chen for the data collection at the State Key Laboratory of Elemento-Organic Chemistry, Nankai University, Tianjin, People’s Republic of China.

supplementary crystallographic information

Comment

Chitin synthesis inhibitors, mainly included benzoylphenylureas and peptidyl nucleosides (Grugier et al., 2000), have been widely used in agriculture and medicine owing to their excellent selectivity (Li et al., 2007). Benzoylphenylureas, discovered in the 1970 s (Grosscurt & Tipker, 1980), are well known as insecticides, but only a few of them show antifungal activity. In order to find new fungicidal chemicals, based on our previous work (Yang et al., 1997; Yang et al., 1998; Yang et al., 2002), 2,6- difluorobenzoyl carbamic acid-5-(4- fluorophenyl)-2-furanmethylester (I), and its analogues were designed through the modifications on the urea linkage of benzoylphenylureas. The compound (I) was synthesized by the reaction of 5- (4-fluorophenyl)-2-furanmethanol and 2,6-difluorobenzoylisocyanate. Finally in the preliminary bioassay, we found it showed obvious antifungal activity against different kinds of strains. To get more information about the structure and the mode of action, we prepared a single-crystal of (I) and its crystal will be reported herein. (I)

The molecular structure of the title compound is given in Fig.1. Single crystals showed clearly that some sort of disorder was present in the structure, containing the atoms C1, C2, C3, C4, C5, C6 and F1. The phenyl group was disordered in two positions with occupy factors 0.42 (3)/0.58 (3). The disordered phenyl group was constrained as a hexagon with C—C distances of 1.39 Å. This compound contains three ring planes: (a) composed of C14, C15, C16, C17, C18, C19, (b) composed of C7, C8, C9, C10, O1 and (c) composed of C1, C2, C3, C4, C5, C6. The dihedral angle between (b) and (c) is 1.58° which infers that the furan ring is almost coplanar with the adjacent benzene ring. In the crystal structure, the carboxyl O and amide NH are involved in N—H···O intermolecular hydrogen bonds. The molecules are linked via intermolecular N—H···O hydrogen bonds to form chains. The data is shown in Table1 and Fig.2.

Experimental

To a solution of 5- (4-fluorophenyl)-2-furanmethanol (2.0 g, 10.4 mmol) dissolved in anhydrous toluene(20 ml), 2,6-difluorobenzoyl isocyanate (2.47 g, 13.5 mmol) was added. Then the mixture was stirred for 30 minutes at room temperature. Liquid was filtered off and the solid was dried. The solid was recrystallized from the solvent of petroleum ether and ethyl acetate (V petroleumether: V ethyl acetate = 2.5: 1) and 2.87 g compound (I) was obtained in 73.5% yield. The colorless crystal was finally got after the second recrystallization.

Refinement

H atoms were placed in calculated positions, with C—H = 0.93, 0.97 Å,and included in the final cycle of refinement using a riding model, with Uiso (H) = 1.2Ueq (parent atom).

Figures

Fig. 1.
The molecular structure of (I), showing 40% probability displacement ellipsoids and the atom-numbering scheme.
Fig. 2.
The crystal packing of (I). Intermolecular hydrogen bonds are shown as dashed lines.

Crystal data

C19H12F3NO4F000 = 768
Mr = 375.30Dx = 1.470 Mg m3
Monoclinic, P2(1)/cMo Kα radiation λ = 0.71073 Å
a = 7.5594 (11) ÅCell parameters from 3023 reflections
b = 12.9878 (19) Åθ = 2.8–23.5º
c = 17.332 (2) ŵ = 0.13 mm1
β = 94.662 (2)ºT = 294 (2) K
V = 1696.0 (4) Å3Block, colourless
Z = 40.26 × 0.20 × 0.14 mm

Data collection

Bruker SMART CCD area-detector diffractometer3453 independent reflections
Radiation source: fine-focus sealed tube2305 reflections with I > 2σ(I)
Monochromator: graphiteRint = 0.026
T = 294(2) Kθmax = 26.4º
phi and ω scansθmin = 2.0º
Absorption correction: multi-scan(SADABS; Sheldrick, 1996)h = −9→6
Tmin = 0.968, Tmax = 0.983k = −15→16
9559 measured reflectionsl = −21→21

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) = 0.103  w = 1/[σ2(Fo2) + (0.0473P)2 + 0.2734P] where P = (Fo2 + 2Fc2)/3
S = 1.00(Δ/σ)max = 0.005
3453 reflectionsΔρmax = 0.16 e Å3
288 parametersΔρmin = −0.17 e Å3
99 restraintsExtinction correction: none
Primary atom site location: structure-invariant direct methods

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*/UeqOcc. (<1)
F10.413 (2)−0.3113 (6)0.0264 (9)0.080 (2)0.42 (3)
C10.2408 (19)−0.0169 (4)−0.0205 (6)0.036 (2)0.42 (3)
C20.309 (2)−0.0746 (6)−0.0790 (6)0.056 (2)0.42 (3)
H2A0.3101−0.0472−0.12850.068*0.42 (3)
C30.374 (2)−0.1731 (6)−0.0634 (7)0.069 (3)0.42 (3)
H3A0.4192−0.2116−0.10250.082*0.42 (3)
C40.3715 (17)−0.2139 (5)0.0107 (8)0.054 (2)0.42 (3)
C50.3038 (15)−0.1563 (6)0.0691 (6)0.048 (2)0.42 (3)
H5A0.3023−0.18360.11860.058*0.42 (3)
C60.2385 (16)−0.0578 (6)0.0535 (5)0.043 (2)0.42 (3)
H6A0.1932−0.01920.09260.051*0.42 (3)
F1'0.4021 (18)−0.3089 (5)0.0520 (10)0.109 (3)0.58 (3)
C1'0.2758 (17)−0.0108 (4)−0.0136 (5)0.046 (2)0.58 (3)
C2'0.3377 (16)−0.0798 (4)−0.0665 (5)0.0563 (19)0.58 (3)
H2'A0.3535−0.0585−0.11670.068*0.58 (3)
C3'0.3759 (14)−0.1808 (4)−0.0444 (7)0.065 (2)0.58 (3)
H3'A0.4173−0.2270−0.07970.078*0.58 (3)
C4'0.3523 (15)−0.2127 (3)0.0307 (7)0.071 (2)0.58 (3)
C5'0.2903 (15)−0.1437 (7)0.0835 (6)0.077 (2)0.58 (3)
H5'A0.2745−0.16500.13370.092*0.58 (3)
C6'0.2521 (14)−0.0427 (7)0.0614 (5)0.061 (2)0.58 (3)
H6'A0.21070.00350.09680.073*0.58 (3)
F20.79946 (16)0.38529 (10)0.18219 (8)0.0850 (4)
F30.46235 (17)0.66668 (10)0.24915 (8)0.0815 (4)
O10.14882 (15)0.15186 (9)0.01943 (6)0.0446 (3)
O20.18983 (15)0.37207 (9)0.08958 (6)0.0447 (3)
O30.27950 (16)0.45938 (9)−0.01226 (6)0.0511 (3)
O40.35555 (19)0.43640 (13)0.22503 (7)0.0758 (5)
N10.4384 (2)0.46921 (12)0.10395 (8)0.0447 (4)
H1A0.514 (2)0.5000 (13)0.0829 (10)0.042 (5)*
C70.2094 (2)0.09129 (15)−0.03758 (10)0.0475 (4)
C80.2100 (3)0.14741 (17)−0.10359 (11)0.0615 (5)
H80.24450.1244−0.15090.074*
C90.1489 (3)0.24670 (16)−0.08727 (10)0.0597 (5)
H90.13610.3017−0.12160.072*
C100.1125 (2)0.24690 (14)−0.01267 (9)0.0448 (4)
C110.0465 (2)0.32610 (14)0.03827 (10)0.0480 (4)
H11A−0.04050.29560.06950.058*
H11B−0.01210.37980.00680.058*
C120.2968 (2)0.43425 (12)0.05510 (9)0.0406 (4)
C130.4595 (2)0.47122 (13)0.18313 (9)0.0440 (4)
C140.6266 (2)0.52450 (13)0.21432 (8)0.0424 (4)
C150.7915 (3)0.48058 (15)0.21366 (10)0.0542 (5)
C160.9447 (3)0.5274 (2)0.24403 (12)0.0678 (6)
H161.05430.49510.24270.081*
C170.9310 (3)0.6231 (2)0.27633 (11)0.0710 (6)
H171.03320.65620.29710.085*
C180.7704 (3)0.67107 (17)0.27869 (11)0.0642 (6)
H180.76200.73610.30060.077*
C190.6231 (3)0.62066 (15)0.24798 (10)0.0518 (5)

Atomic displacement parameters (Å2)

U11U22U33U12U13U23
F10.092 (4)0.048 (3)0.099 (5)0.015 (2)0.008 (3)−0.003 (3)
C10.012 (4)0.049 (4)0.047 (3)−0.015 (2)−0.004 (3)−0.016 (3)
C20.040 (5)0.064 (5)0.063 (4)−0.007 (3)−0.009 (4)−0.015 (3)
C30.062 (5)0.084 (6)0.061 (4)−0.012 (4)0.010 (4)−0.016 (3)
C40.045 (4)0.048 (5)0.071 (5)−0.005 (3)0.010 (3)0.001 (3)
C50.048 (4)0.036 (4)0.061 (4)0.004 (3)0.006 (3)0.007 (3)
C60.040 (4)0.032 (3)0.057 (4)−0.006 (3)0.011 (3)−0.019 (3)
F1'0.118 (3)0.068 (3)0.142 (6)0.020 (2)0.013 (5)−0.022 (3)
C1'0.024 (4)0.057 (3)0.057 (3)−0.017 (2)−0.002 (2)−0.022 (2)
C2'0.037 (3)0.069 (4)0.062 (3)0.001 (2)−0.002 (3)−0.026 (2)
C3'0.052 (3)0.054 (4)0.089 (5)0.003 (3)0.004 (3)−0.035 (3)
C4'0.051 (3)0.053 (4)0.109 (5)0.004 (3)0.009 (4)−0.031 (4)
C5'0.076 (4)0.072 (4)0.084 (4)−0.001 (3)0.016 (3)−0.028 (3)
C6'0.062 (4)0.051 (3)0.069 (4)−0.007 (3)−0.001 (3)−0.016 (3)
F20.0776 (9)0.0746 (9)0.1041 (10)0.0198 (7)0.0145 (7)−0.0250 (7)
F30.0814 (9)0.0739 (8)0.0900 (9)0.0234 (7)0.0129 (7)−0.0138 (7)
O10.0467 (7)0.0500 (7)0.0377 (6)−0.0049 (5)0.0076 (5)−0.0051 (5)
O20.0493 (7)0.0469 (7)0.0385 (6)−0.0105 (5)0.0074 (5)0.0014 (5)
O30.0586 (8)0.0567 (8)0.0374 (6)−0.0106 (6)0.0007 (5)0.0091 (6)
O40.0671 (9)0.1219 (13)0.0399 (7)−0.0305 (9)0.0139 (7)0.0033 (7)
N10.0487 (9)0.0521 (9)0.0340 (7)−0.0146 (7)0.0074 (6)0.0037 (6)
C70.0425 (10)0.0562 (12)0.0446 (10)−0.0107 (8)0.0087 (8)−0.0159 (8)
C80.0718 (13)0.0758 (15)0.0388 (10)−0.0165 (11)0.0153 (9)−0.0127 (10)
C90.0743 (13)0.0650 (13)0.0402 (10)−0.0149 (10)0.0071 (9)0.0002 (9)
C100.0445 (10)0.0492 (11)0.0407 (9)−0.0095 (8)0.0030 (7)−0.0008 (8)
C110.0415 (10)0.0544 (11)0.0484 (10)−0.0075 (8)0.0048 (8)−0.0012 (8)
C120.0451 (10)0.0395 (9)0.0380 (9)−0.0020 (7)0.0073 (7)0.0009 (7)
C130.0470 (10)0.0512 (10)0.0348 (8)0.0002 (8)0.0098 (7)0.0020 (8)
C140.0466 (10)0.0522 (11)0.0289 (8)0.0009 (8)0.0065 (7)0.0004 (7)
C150.0585 (12)0.0591 (12)0.0456 (10)0.0072 (9)0.0077 (9)−0.0039 (9)
C160.0449 (12)0.0960 (18)0.0613 (12)0.0041 (11)−0.0034 (9)0.0085 (12)
C170.0709 (15)0.0912 (18)0.0484 (11)−0.0217 (13)−0.0109 (10)0.0005 (11)
C180.0870 (16)0.0616 (13)0.0431 (10)−0.0113 (12)−0.0012 (10)−0.0085 (9)
C190.0588 (12)0.0580 (12)0.0389 (9)0.0066 (9)0.0058 (8)−0.0021 (8)

Geometric parameters (Å, °)

F1—C41.327 (6)O1—C101.372 (2)
C1—C21.3900O2—C121.3196 (18)
C1—C61.3900O2—C111.4710 (19)
C1—C71.452 (4)O3—C121.2091 (18)
C2—C31.3900O4—C131.2008 (19)
C2—H2A0.9300N1—C131.369 (2)
C3—C41.3900N1—C121.386 (2)
C3—H3A0.9300N1—H1A0.810 (17)
C4—C51.3900C7—C81.357 (3)
C5—C61.3900C8—C91.406 (3)
C5—H5A0.9300C8—H80.9300
C6—H6A0.9300C9—C101.343 (2)
F1'—C4'1.347 (6)C9—H90.9300
C1'—C2'1.3900C10—C111.469 (2)
C1'—C6'1.3900C11—H11A0.9700
C1'—C71.466 (4)C11—H11B0.9700
C2'—C3'1.3900C13—C141.502 (2)
C2'—H2'A0.9300C14—C151.372 (2)
C3'—C4'1.3900C14—C191.380 (2)
C3'—H3'A0.9300C15—C161.375 (3)
C4'—C5'1.3900C16—C171.371 (3)
C5'—C6'1.3900C16—H160.9300
C5'—H5'A0.9300C17—C181.369 (3)
C6'—H6'A0.9300C17—H170.9300
F2—C151.356 (2)C18—C191.362 (3)
F3—C191.356 (2)C18—H180.9300
O1—C71.3705 (19)
C2—C1—C6120.0O1—C7—C1117.9 (4)
C2—C1—C7115.9 (5)C8—C7—C1'134.4 (3)
C6—C1—C7122.9 (5)O1—C7—C1'116.2 (3)
C1—C2—C3120.0C1—C7—C1'11.5 (9)
C1—C2—H2A120.0C7—C8—C9107.42 (16)
C3—C2—H2A120.0C7—C8—H8126.3
C4—C3—C2120.0C9—C8—H8126.3
C4—C3—H3A120.0C10—C9—C8106.95 (18)
C2—C3—H3A120.0C10—C9—H9126.5
F1—C4—C3122.2 (6)C8—C9—H9126.5
F1—C4—C5117.4 (6)C9—C10—O1109.79 (16)
C3—C4—C5120.0C9—C10—C11133.30 (18)
C6—C5—C4120.0O1—C10—C11116.91 (14)
C6—C5—H5A120.0C10—C11—O2112.23 (14)
C4—C5—H5A120.0C10—C11—H11A109.2
C5—C6—C1120.0O2—C11—H11A109.2
C5—C6—H6A120.0C10—C11—H11B109.2
C1—C6—H6A120.0O2—C11—H11B109.2
C2'—C1'—C6'120.0H11A—C11—H11B107.9
C2'—C1'—C7121.5 (4)O3—C12—O2125.48 (15)
C6'—C1'—C7117.9 (5)O3—C12—N1121.25 (15)
C3'—C2'—C1'120.0O2—C12—N1113.27 (14)
C3'—C2'—H2'A120.0O4—C13—N1124.77 (17)
C1'—C2'—H2'A120.0O4—C13—C14121.89 (15)
C2'—C3'—C4'120.0N1—C13—C14113.32 (14)
C2'—C3'—H3'A120.0C15—C14—C19115.38 (17)
C4'—C3'—H3'A120.0C15—C14—C13122.94 (16)
F1'—C4'—C5'121.2 (5)C19—C14—C13121.66 (15)
F1'—C4'—C3'118.6 (5)F2—C15—C14116.95 (17)
C5'—C4'—C3'120.0F2—C15—C16119.58 (18)
C6'—C5'—C4'120.0C14—C15—C16123.46 (19)
C6'—C5'—H5'A120.0C17—C16—C15117.9 (2)
C4'—C5'—H5'A120.0C17—C16—H16121.1
C5'—C6'—C1'120.0C15—C16—H16121.1
C5'—C6'—H6'A120.0C18—C17—C16121.5 (2)
C1'—C6'—H6'A120.0C18—C17—H17119.3
C7—O1—C10106.94 (13)C16—C17—H17119.3
C12—O2—C11115.00 (12)C19—C18—C17117.9 (2)
C13—N1—C12129.79 (15)C19—C18—H18121.0
C13—N1—H1A114.4 (12)C17—C18—H18121.0
C12—N1—H1A115.2 (12)F3—C19—C18119.16 (18)
C8—C7—O1108.89 (17)F3—C19—C14116.96 (17)
C8—C7—C1132.8 (4)C18—C19—C14123.87 (18)
C6—C1—C2—C30.0O1—C7—C8—C90.4 (2)
C7—C1—C2—C3167.9 (11)C1—C7—C8—C9172.9 (8)
C1—C2—C3—C40.0C1'—C7—C8—C9−171.4 (8)
C2—C3—C4—F1172.2 (14)C7—C8—C9—C10−0.4 (2)
C2—C3—C4—C50.0C8—C9—C10—O10.3 (2)
F1—C4—C5—C6−172.6 (13)C8—C9—C10—C11179.54 (18)
C3—C4—C5—C60.0C7—O1—C10—C9−0.07 (18)
C4—C5—C6—C10.0C7—O1—C10—C11−179.44 (14)
C2—C1—C6—C50.0C9—C10—C11—O2−100.7 (2)
C7—C1—C6—C5−167.1 (12)O1—C10—C11—O278.50 (18)
C6'—C1'—C2'—C3'0.0C12—O2—C11—C1072.38 (18)
C7—C1'—C2'—C3'−170.9 (11)C11—O2—C12—O34.2 (2)
C1'—C2'—C3'—C4'0.0C11—O2—C12—N1−174.94 (13)
C2'—C3'—C4'—F1'−175.4 (12)C13—N1—C12—O3162.21 (17)
C2'—C3'—C4'—C5'0.0C13—N1—C12—O2−18.6 (3)
F1'—C4'—C5'—C6'175.3 (12)C12—N1—C13—O43.9 (3)
C3'—C4'—C5'—C6'0.0C12—N1—C13—C14−174.66 (16)
C4'—C5'—C6'—C1'0.0O4—C13—C14—C15106.4 (2)
C2'—C1'—C6'—C5'0.0N1—C13—C14—C15−75.0 (2)
C7—C1'—C6'—C5'171.2 (10)O4—C13—C14—C19−71.6 (2)
C10—O1—C7—C8−0.21 (18)N1—C13—C14—C19107.02 (18)
C10—O1—C7—C1−174.0 (7)C19—C14—C15—F2178.90 (15)
C10—O1—C7—C1'173.2 (6)C13—C14—C15—F20.8 (2)
C2—C1—C7—C810.4 (11)C19—C14—C15—C160.0 (3)
C6—C1—C7—C8177.9 (5)C13—C14—C15—C16−178.07 (17)
C2—C1—C7—O1−177.7 (5)F2—C15—C16—C17−179.09 (18)
C6—C1—C7—O1−10.1 (11)C14—C15—C16—C17−0.2 (3)
C2—C1—C7—C1'−93 (3)C15—C16—C17—C180.2 (3)
C6—C1—C7—C1'75 (3)C16—C17—C18—C190.1 (3)
C2'—C1'—C7—C8−9.8 (11)C17—C18—C19—F3−179.62 (17)
C6'—C1'—C7—C8179.1 (4)C17—C18—C19—C14−0.4 (3)
C2'—C1'—C7—O1178.8 (5)C15—C14—C19—F3179.55 (15)
C6'—C1'—C7—O17.8 (8)C13—C14—C19—F3−2.3 (2)
C2'—C1'—C7—C178 (3)C15—C14—C19—C180.3 (3)
C6'—C1'—C7—C1−93 (3)C13—C14—C19—C18178.41 (16)

Hydrogen-bond geometry (Å, °)

D—H···AD—HH···AD···AD—H···A
N1—H1A···O3i0.810 (17)2.126 (18)2.9129 (19)164.0 (17)

Symmetry codes: (i) −x+1, −y+1, −z.

Footnotes

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: SG2221).

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