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Acta Crystallogr Sect E Struct Rep Online. 2010 December 1; 66(Pt 12): o3075.
Published online 2010 November 6. doi:  10.1107/S1600536810044491
PMCID: PMC3011766

3-Ethyl 2-methyl 8-bromo-2-phenyl-1,2,3,3a,4,9b-hexa­hydro­chromeno[4,3-b]pyrrole-2,3-dicarboxyl­ate

Abstract

The title compound, C22H22BrNO5, was synthesized by the intra­molecular cyclo­addition reaction of (E)-ethyl 4-(4-bromo-2-formyl­phen­oxy)but-2-enoate and methyl 2-amino-2-phenyl­acetate. The pyrrolidine and 3,4-dihydro-2H-pyran rings exhibit envelope conformations. The two benzene rings are twisted to each other at a dihedral angle of 59.36 (18)°. The eth­oxy group of the ester unit is disordered over two sites with an occupancy ratio of 0.503 (11):0.497 (11). Weak inter­molecular C—H(...)O hydrogen bonding is present in the crystal structure.

Related literature

For the biological activity of pyrrolidine derivatives, see: Coldham & Hufton (2005 [triangle]); Grigg (1995 [triangle]); Kravchenko et al. (2005 [triangle]); Nair & Suja (2007 [triangle]); Pandey et al. (2006 [triangle]); Sardina & Rapoport (1996 [triangle]); Witherup et al. (1995 [triangle]). For a related structure, see: Yu et al. (2007 [triangle]).

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Object name is e-66-o3075-scheme1.jpg

Experimental

Crystal data

  • C22H22BrNO5
  • M r = 460.32
  • Monoclinic, An external file that holds a picture, illustration, etc.
Object name is e-66-o3075-efi1.jpg
  • a = 11.1046 (8) Å
  • b = 11.1633 (6) Å
  • c = 17.9779 (9) Å
  • β = 107.856 (6)°
  • V = 2121.3 (2) Å3
  • Z = 4
  • Mo Kα radiation
  • μ = 1.97 mm−1
  • T = 293 K
  • 0.50 × 0.42 × 0.38 mm

Data collection

  • Oxford diffraction Gemini S Ultra diffractometer
  • Absorption correction: multi-scan (CrysAlis PRO; Oxford Diffraction, 2009 [triangle]) T min = 0.439, T max = 0.521
  • 10601 measured reflections
  • 3609 independent reflections
  • 2015 reflections with I > 2σ(I)
  • R int = 0.027

Refinement

  • R[F 2 > 2σ(F 2)] = 0.047
  • wR(F 2) = 0.137
  • S = 1.06
  • 3609 reflections
  • 293 parameters
  • 47 restraints
  • H-atom parameters constrained
  • Δρmax = 0.53 e Å−3
  • Δρmin = −0.36 e Å−3

Data collection: CrysAlis CCD (Oxford Diffraction, 2008 [triangle]); cell refinement: CrysAlis RED (Oxford Diffraction, 2008 [triangle]); data reduction: CrysAlis RED; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 [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: SHELXL97.

Table 1
Hydrogen-bond geometry (Å, °)

Supplementary Material

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536810044491/xu5063sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536810044491/xu5063Isup2.hkl

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

Acknowledgments

The diffraction measurements were made at The Centre for Testing and Analysis, Chengdu Branch, Chinese Academy of Sciences. We acknowledge financial support from China West Normal University.

supplementary crystallographic information

Comment

Pyrrolidine containing compounds are an important class of heterocyclic compounds with wide spread applications to the synthesis of biologically active compounds and natural products. (Coldham et al., 2005; Grigg et al., 1995; Kravchenko et al., 2005; Nair et al., 2007; Pandey et al., 2006; Sardina et al., 1996; Witherup et al. 1995). Its crystal structure is reported here.

The molecular structure of (I) is shown in Fig. 1. Bond lengths and angles in (I) are normal. The pyrrolidine ring possesses an envelope conformation. The dihedral angle between the C1—C6 and C12—C17 benzene planes is 59.38 (8)°. The crystal packing is stabilized by C—H···0 hydrogen bonding (Table 1).

Experimental

(E)-Ethyl 4-(4-bromo-2-formylphenoxy)but-2-enoate (0.0374 g, 0.12 mmol) and phosphenous acid (5 mg, 0.01 mmol) were added to a solution of methyl 2-amino-2-phenylacetate (0.016 g, 0.1 mmol) in dichloromethane (1 ml). After the mixture had been stirred at 298 K for 24 h, the reaction was quenched with a saturated solution of sodium bicarbonate (5 ml). The mixture was extracted with ethyl acetate, evaporated and separated by flash chromatograghy. A colourless powder was obtained. Single crystals suitable for X-ray diffraction were obtained by slow evaporation of an ethanol solution.

Refinement

H atom on N atom was located in a difference Fourier map and refined isotropically. Other H atoms were placed in calculated positions with C—H = 0.93–0.98 Å, and refined using a riding model, with Uiso(H) =1.2Ueq(C).

Figures

Fig. 1.
The molecular structure of (I) with 30% probability displacement ellipsoids (arbitrary spheres for H atoms).

Crystal data

C22H22BrNO5F(000) = 944
Mr = 460.32Dx = 1.441 Mg m3
Monoclinic, P2/cMo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ycCell parameters from 4173 reflections
a = 11.1046 (8) Åθ = 3.0–29.1°
b = 11.1633 (6) ŵ = 1.97 mm1
c = 17.9779 (9) ÅT = 293 K
β = 107.856 (6)°Block, colorless
V = 2121.3 (2) Å30.50 × 0.42 × 0.38 mm
Z = 4

Data collection

Oxford diffraction Gemini S Ultra diffractometer3609 independent reflections
Radiation source: Enhance (Mo) X-ray Source2015 reflections with I > 2σ(I)
graphiteRint = 0.027
Detector resolution: 15.9149 pixels mm-1θmax = 25.0°, θmin = 3.0°
ω scansh = −10→13
Absorption correction: multi-scan (CrysAlis PRO; Oxford Diffraction, 2009)k = −13→13
Tmin = 0.439, Tmax = 0.521l = −21→14
10601 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)] = 0.047H-atom parameters constrained
wR(F2) = 0.137w = 1/[σ2(Fo2) + (0.070P)2] where P = (Fo2 + 2Fc2)/3
S = 1.06(Δ/σ)max < 0.001
3609 reflectionsΔρmax = 0.53 e Å3
293 parametersΔρmin = −0.36 e Å3
47 restraintsExtinction correction: SHELXL97 (Sheldrick, 2008), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
Primary atom site location: structure-invariant direct methodsExtinction coefficient: 0.0095 (11)

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)
Br10.72424 (6)0.38095 (6)0.29704 (3)0.1076 (4)
O10.6457 (3)0.3997 (2)−0.04947 (15)0.0595 (8)
O20.4138 (4)0.0088 (4)−0.1551 (2)0.1059 (12)
O40.1640 (3)−0.0047 (2)−0.11722 (17)0.0635 (8)
O50.3115 (4)−0.0409 (3)−0.0070 (2)0.1175 (15)
N10.3815 (3)0.1909 (3)0.01891 (15)0.0449 (8)
H10.42430.12310.04200.054*
C10.6979 (4)0.3818 (3)0.1873 (2)0.0533 (11)
C20.7856 (4)0.4379 (3)0.1590 (2)0.0551 (11)
H20.85770.47230.19320.066*
C30.7649 (4)0.4422 (3)0.0789 (2)0.0511 (10)
H30.82300.48030.05900.061*
C40.6575 (4)0.3898 (3)0.0286 (2)0.0448 (10)
C50.5689 (3)0.3342 (3)0.0584 (2)0.0410 (9)
C60.5906 (4)0.3296 (3)0.1377 (2)0.0473 (10)
H60.53320.29130.15790.057*
C70.4515 (3)0.2897 (3)−0.00127 (18)0.0367 (9)
H70.39310.3577−0.01540.044*
C80.4777 (3)0.2507 (3)−0.07426 (19)0.0442 (9)
H80.53860.1845−0.06170.053*
C90.5333 (4)0.3526 (3)−0.1078 (2)0.0553 (11)
H9B0.55560.3247−0.15300.066*
H9A0.47090.4158−0.12480.066*
C100.3478 (3)0.2018 (3)−0.1234 (2)0.0475 (10)
H100.29770.2678−0.15350.057*
C110.2866 (3)0.1615 (3)−0.0566 (2)0.0436 (10)
C120.1641 (3)0.2301 (3)−0.0647 (2)0.0387 (9)
C130.0758 (3)0.2521 (3)−0.1367 (2)0.0466 (10)
H130.09130.2254−0.18190.056*
C14−0.0350 (4)0.3130 (4)−0.1424 (2)0.0563 (11)
H14−0.09260.3285−0.19120.068*
C15−0.0600 (4)0.3508 (3)−0.0757 (3)0.0593 (11)
H15−0.13550.3900−0.07920.071*
C160.0266 (4)0.3306 (3)−0.0044 (2)0.0570 (11)
H160.01080.35810.04060.068*
C170.1375 (4)0.2696 (3)0.0017 (2)0.0457 (9)
H170.19480.25490.05070.055*
C180.2588 (4)0.0276 (4)−0.0581 (2)0.0618 (12)
C190.1333 (5)−0.1312 (3)−0.1246 (3)0.0905 (17)
H19B0.0627−0.1443−0.17060.136*
H19A0.1119−0.1576−0.07940.136*
H19C0.2050−0.1757−0.12870.136*
C200.3562 (4)0.1050 (5)−0.1778 (3)0.0756 (15)
O3A0.2757 (11)0.1020 (10)−0.2478 (4)0.077 (4)0.503 (11)
C21A0.2932 (13)−0.0032 (13)−0.2963 (6)0.085 (4)0.503 (11)
H21A0.3737−0.0010−0.30690.102*0.503 (11)
H21D0.2828−0.0796−0.27330.102*0.503 (11)
C22A0.1844 (14)0.0266 (14)−0.3665 (7)0.114 (5)0.503 (11)
H22A0.1644−0.0415−0.40070.137*0.503 (11)
H22B0.20650.0931−0.39350.137*0.503 (11)
H22C0.11220.0472−0.35040.137*0.503 (11)
O3B0.3037 (11)0.1466 (10)−0.2494 (4)0.076 (4)0.497 (11)
C21B0.2937 (12)0.0691 (13)−0.3194 (7)0.087 (4)0.497 (11)
H21B0.27330.1182−0.36620.104*0.497 (11)
H21C0.37400.0299−0.31350.104*0.497 (11)
C22B0.1929 (17)−0.0226 (13)−0.3272 (11)0.119 (5)0.497 (11)
H22D0.2015−0.0845−0.36240.143*0.497 (11)
H22E0.11140.0145−0.34740.143*0.497 (11)
H22F0.2011−0.0568−0.27690.143*0.497 (11)

Atomic displacement parameters (Å2)

U11U22U33U12U13U23
Br10.1153 (6)0.1448 (6)0.0475 (3)−0.0492 (4)0.0024 (3)−0.0107 (3)
O10.0545 (19)0.0725 (19)0.0533 (18)−0.0083 (14)0.0191 (14)0.0055 (13)
O20.088 (3)0.098 (3)0.127 (3)0.007 (2)0.026 (2)−0.052 (2)
O40.0518 (19)0.0337 (16)0.089 (2)0.0030 (13)−0.0016 (15)−0.0052 (13)
O50.119 (3)0.059 (2)0.123 (3)0.009 (2)−0.039 (2)0.015 (2)
N10.0409 (19)0.0413 (18)0.0432 (17)0.0029 (15)−0.0008 (14)0.0036 (14)
C10.058 (3)0.051 (2)0.042 (2)−0.004 (2)0.003 (2)−0.0067 (18)
C20.047 (3)0.041 (2)0.068 (3)−0.003 (2)0.005 (2)−0.008 (2)
C30.038 (3)0.043 (2)0.074 (3)0.0021 (18)0.018 (2)0.004 (2)
C40.044 (3)0.035 (2)0.055 (3)0.0114 (19)0.014 (2)0.0039 (18)
C50.040 (2)0.030 (2)0.052 (2)0.0079 (17)0.0133 (19)−0.0003 (17)
C60.049 (3)0.045 (2)0.047 (2)−0.0046 (19)0.0130 (19)0.0014 (18)
C70.037 (2)0.034 (2)0.0370 (19)0.0028 (17)0.0082 (17)0.0018 (15)
C80.036 (2)0.042 (2)0.054 (2)0.0083 (17)0.0133 (18)−0.0024 (18)
C90.058 (3)0.063 (3)0.047 (2)0.006 (2)0.020 (2)−0.0011 (19)
C100.043 (2)0.056 (3)0.041 (2)0.0141 (19)0.0085 (18)−0.0065 (18)
C110.036 (2)0.038 (2)0.050 (2)0.0032 (17)0.0018 (17)−0.0037 (17)
C120.039 (2)0.0276 (19)0.046 (2)−0.0025 (16)0.0078 (18)−0.0004 (16)
C130.044 (3)0.050 (2)0.043 (2)0.0046 (19)0.0091 (18)−0.0048 (17)
C140.047 (3)0.059 (3)0.056 (3)0.009 (2)0.005 (2)−0.006 (2)
C150.044 (3)0.052 (3)0.085 (3)0.010 (2)0.024 (2)0.006 (2)
C160.062 (3)0.055 (3)0.061 (3)0.004 (2)0.029 (2)−0.003 (2)
C170.045 (3)0.044 (2)0.049 (2)−0.0008 (19)0.0160 (19)0.0012 (17)
C180.057 (3)0.043 (3)0.067 (3)0.013 (2)−0.007 (2)0.002 (2)
C190.080 (4)0.038 (3)0.134 (5)−0.008 (2)0.004 (3)−0.009 (2)
C200.046 (3)0.101 (4)0.076 (4)0.014 (3)0.012 (3)−0.034 (3)
O3A0.076 (7)0.074 (6)0.064 (5)−0.009 (5)−0.006 (4)−0.048 (4)
C21A0.096 (6)0.100 (7)0.060 (6)−0.012 (6)0.024 (5)−0.031 (5)
C22A0.128 (8)0.095 (8)0.103 (8)−0.006 (6)0.011 (6)−0.028 (6)
O3B0.062 (6)0.103 (9)0.058 (5)−0.024 (6)0.012 (4)−0.057 (5)
C21B0.088 (6)0.106 (7)0.065 (6)−0.004 (6)0.022 (5)−0.023 (6)
C22B0.120 (8)0.120 (9)0.116 (9)−0.011 (7)0.034 (7)−0.036 (7)

Geometric parameters (Å, °)

Br1—C11.904 (4)C11—C121.530 (5)
O1—C41.374 (4)C12—C131.384 (4)
O1—C91.460 (5)C12—C171.387 (5)
O2—C201.253 (6)C13—C141.382 (5)
O4—C181.297 (4)C13—H130.9300
O4—C191.449 (4)C14—C151.377 (5)
O5—C181.201 (5)C14—H140.9300
N1—C71.458 (4)C15—C161.365 (6)
N1—C111.478 (4)C15—H150.9300
N1—H10.9221C16—C171.382 (5)
C1—C61.379 (5)C16—H160.9300
C1—C21.379 (6)C17—H170.9300
C2—C31.387 (5)C19—H19B0.9600
C2—H20.9300C19—H19A0.9600
C3—C41.387 (5)C19—H19C0.9600
C3—H30.9300C20—O3A1.301 (8)
C4—C51.400 (5)C20—O3B1.323 (8)
C5—C61.372 (5)O3A—C21A1.510 (9)
C5—C71.496 (5)C21A—C22A1.493 (10)
C6—H60.9300C21A—H21A0.9700
C7—C81.493 (5)C21A—H21D0.9700
C7—H70.9800C22A—H22A0.9600
C8—C91.505 (5)C22A—H22B0.9600
C8—C101.542 (5)C22A—H22C0.9600
C8—H80.9800O3B—C21B1.503 (9)
C9—H9B0.9700C21B—C22B1.491 (10)
C9—H9A0.9700C21B—H21B0.9700
C10—C201.480 (6)C21B—H21C0.9700
C10—C111.614 (5)C22B—H22D0.9600
C10—H100.9800C22B—H22E0.9600
C11—C181.524 (5)C22B—H22F0.9600
C4—O1—C9119.8 (3)C13—C12—C17118.1 (3)
C18—O4—C19117.1 (3)C13—C12—C11122.2 (3)
C7—N1—C11102.9 (3)C17—C12—C11119.7 (3)
C7—N1—H1119.4C14—C13—C12121.1 (3)
C11—N1—H1110.8C14—C13—H13119.5
C6—C1—C2121.4 (4)C12—C13—H13119.5
C6—C1—Br1119.7 (3)C15—C14—C13119.9 (4)
C2—C1—Br1118.8 (3)C15—C14—H14120.0
C1—C2—C3119.2 (4)C13—C14—H14120.0
C1—C2—H2120.4C16—C15—C14119.7 (4)
C3—C2—H2120.4C16—C15—H15120.2
C4—C3—C2119.8 (4)C14—C15—H15120.2
C4—C3—H3120.1C15—C16—C17120.7 (4)
C2—C3—H3120.1C15—C16—H16119.7
O1—C4—C3115.2 (3)C17—C16—H16119.7
O1—C4—C5124.6 (3)C16—C17—C12120.5 (3)
C3—C4—C5120.2 (4)C16—C17—H17119.7
C6—C5—C4119.6 (3)C12—C17—H17119.7
C6—C5—C7124.7 (3)O5—C18—O4122.2 (4)
C4—C5—C7115.7 (3)O5—C18—C11124.2 (4)
C5—C6—C1119.8 (4)O4—C18—C11113.4 (3)
C5—C6—H6120.1O4—C19—H19B109.5
C1—C6—H6120.1O4—C19—H19A109.5
N1—C7—C8105.1 (3)H19B—C19—H19A109.5
N1—C7—C5119.1 (3)O4—C19—H19C109.5
C8—C7—C5111.4 (3)H19B—C19—H19C109.5
N1—C7—H7106.8H19A—C19—H19C109.5
C8—C7—H7106.8O2—C20—O3A115.1 (6)
C5—C7—H7106.8O2—C20—O3B130.2 (6)
C7—C8—C9110.3 (3)O2—C20—C10122.7 (5)
C7—C8—C10101.9 (3)O3A—C20—C10119.7 (6)
C9—C8—C10117.7 (3)O3B—C20—C10106.8 (6)
C7—C8—H8108.9C20—O3A—C21A114.0 (8)
C9—C8—H8108.9C22A—C21A—O3A95.8 (8)
C10—C8—H8108.9C22A—C21A—H21A112.6
O1—C9—C8110.5 (3)O3A—C21A—H21A112.6
O1—C9—H9B109.6C22A—C21A—H21D112.6
C8—C9—H9B109.6O3A—C21A—H21D112.6
O1—C9—H9A109.6H21A—C21A—H21D110.1
C8—C9—H9A109.6C20—O3B—C21B120.7 (9)
H9B—C9—H9A108.1C22B—C21B—O3B109.6 (10)
C20—C10—C8113.6 (3)C22B—C21B—H21B109.8
C20—C10—C11114.5 (4)O3B—C21B—H21B109.8
C8—C10—C11101.9 (3)C22B—C21B—H21C109.8
C20—C10—H10108.9O3B—C21B—H21C109.8
C8—C10—H10108.9H21B—C21B—H21C108.2
C11—C10—H10108.9C21B—C22B—H22D109.5
N1—C11—C18108.5 (3)C21B—C22B—H22E109.5
N1—C11—C12109.8 (3)H22D—C22B—H22E109.5
C18—C11—C12108.7 (3)C21B—C22B—H22F109.5
N1—C11—C10106.1 (3)H22D—C22B—H22F109.5
C18—C11—C10112.9 (3)H22E—C22B—H22F109.5
C12—C11—C10110.8 (3)
C6—C1—C2—C30.3 (6)C20—C10—C11—C12−117.3 (3)
Br1—C1—C2—C3−177.9 (3)C8—C10—C11—C12119.7 (3)
C1—C2—C3—C4−0.4 (6)N1—C11—C12—C13158.3 (3)
C9—O1—C4—C3−177.2 (3)C18—C11—C12—C13−83.2 (4)
C9—O1—C4—C51.3 (5)C10—C11—C12—C1341.4 (4)
C2—C3—C4—O1179.6 (3)N1—C11—C12—C17−23.5 (4)
C2—C3—C4—C51.1 (5)C18—C11—C12—C1795.1 (4)
O1—C4—C5—C6−180.0 (3)C10—C11—C12—C17−140.4 (3)
C3—C4—C5—C6−1.6 (5)C17—C12—C13—C140.9 (5)
O1—C4—C5—C7−3.3 (5)C11—C12—C13—C14179.2 (3)
C3—C4—C5—C7175.1 (3)C12—C13—C14—C15−1.3 (6)
C4—C5—C6—C11.5 (5)C13—C14—C15—C161.8 (6)
C7—C5—C6—C1−174.9 (3)C14—C15—C16—C17−1.8 (6)
C2—C1—C6—C5−0.9 (6)C15—C16—C17—C121.4 (6)
Br1—C1—C6—C5177.4 (3)C13—C12—C17—C16−1.0 (5)
C11—N1—C7—C8−45.9 (3)C11—C12—C17—C16−179.3 (3)
C11—N1—C7—C5−171.6 (3)C19—O4—C18—O5−7.6 (7)
C6—C5—C7—N1−29.2 (5)C19—O4—C18—C11178.1 (4)
C4—C5—C7—N1154.4 (3)N1—C11—C18—O5−3.3 (6)
C6—C5—C7—C8−151.8 (3)C12—C11—C18—O5−122.7 (5)
C4—C5—C7—C831.7 (4)C10—C11—C18—O5114.1 (5)
N1—C7—C8—C9171.7 (3)N1—C11—C18—O4170.9 (3)
C5—C7—C8—C9−57.9 (4)C12—C11—C18—O451.5 (4)
N1—C7—C8—C1046.0 (3)C10—C11—C18—O4−71.8 (4)
C5—C7—C8—C10176.4 (3)C8—C10—C20—O259.3 (6)
C4—O1—C9—C8−27.3 (4)C11—C10—C20—O2−57.1 (6)
C7—C8—C9—O155.1 (4)C8—C10—C20—O3A−139.9 (8)
C10—C8—C9—O1171.3 (3)C11—C10—C20—O3A103.6 (9)
C7—C8—C10—C20−150.5 (4)C8—C10—C20—O3B−115.1 (7)
C9—C8—C10—C2088.9 (5)C11—C10—C20—O3B128.4 (7)
C7—C8—C10—C11−26.8 (3)O2—C20—O3A—C21A−16.4 (14)
C9—C8—C10—C11−147.5 (3)O3B—C20—O3A—C21A115 (3)
C7—N1—C11—C18148.3 (3)C10—C20—O3A—C21A−178.5 (9)
C7—N1—C11—C12−93.0 (3)C20—O3A—C21A—C22A178.4 (15)
C7—N1—C11—C1026.7 (3)O2—C20—O3B—C21B7.6 (16)
C20—C10—C11—N1123.6 (4)O3A—C20—O3B—C21B−54.6 (19)
C8—C10—C11—N10.5 (3)C10—C20—O3B—C21B−178.5 (9)
C20—C10—C11—C184.8 (4)C20—O3B—C21B—C22B74 (2)
C8—C10—C11—C18−118.2 (3)

Hydrogen-bond geometry (Å, °)

D—H···AD—HH···AD···AD—H···A
C8—H8···O5i0.982.373.317 (5)163 (1)

Symmetry codes: (i) −x+1, −y, −z.

Footnotes

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: XU5063).

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