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The oxime derivative of [1.1.1]cyclophane cyclotriveratrylene (CTV) was ring expanded utilizing a Beckmann rearrangement to provide a ten-membered N-acetyl macrocyclic amide that crystallizes as a chloroform monosolvate in columnar assemblies manifesting an unusual disorder within the crystal. Columns made up of this structure consist of infinite columnar assemblies of alternating D and L enantiomers and therefore necessarily are made up of a racemate, yet the chiralities of individual molecules in adjacent columns are independent of one another, leading to the overall formation of a two-dimensional solid solution. The random arrangement of the columns within the structure leads to the emergence of a crystallographic mirror plane not reflected by the molecular symmetry, to a change of symmetry from Pna21 to Pnma and to whole-molecule disorder of the bowl-shaped molecules within the columns.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S0108768109002134/ry5022sup1.cif
Contains datablocks global, I

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S0108768109002134/ry5022Isup2.hkl
Contains datablock I

pdf

Portable Document Format (PDF) file https://doi.org/10.1107/S0108768109002134/ry5022sup3.pdf
NMR spectra, and TGA and DSC data

CCDC reference: 737458

Computing details top

Data collection: Apex2 v2.1-4 (Bruker, 2007); cell refinement: Apex2 v2.1-4; data reduction: Apex2 v2.1-4; program(s) used to solve structure: SHELXTL 6.14 (Bruker, 2000-2003); program(s) used to refine structure: SHELXTL 6.14; molecular graphics: SHELXTL 6.14; software used to prepare material for publication: SHELXTL 6.14.

Figures top
[Figure 1]
[Figure 2]
[Figure 3]
[Figure 4]
(I) top
Crystal data top
C29H31NO8·CHCl3Dx = 1.445 Mg m3
Mr = 640.92Mo Kα radiation, λ = 0.71073 Å
Orthorhombic, PnmaCell parameters from 5245 reflections
a = 16.7247 (18) Åθ = 2.2–30.1°
b = 15.7070 (16) ŵ = 0.36 mm1
c = 11.2154 (11) ÅT = 100 K
V = 2946.2 (5) Å3Plate, yellow
Z = 40.60 × 0.60 × 0.27 mm
F(000) = 1336
Data collection top
Bruker AXS SMART APEX CCD
diffractometer
3783 independent reflections
Radiation source: fine-focus sealed tube2924 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.031
ω scansθmax = 28.3°, θmin = 2.2°
Absorption correction: multi-scan
Apex2 v2.1-4 (Bruker, 2007)
h = 2222
Tmin = 0.768, Tmax = 0.906k = 1820
19031 measured reflectionsl = 1314
Refinement top
Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.077Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.222H-atom parameters constrained
S = 1.04 w = 1/[σ2(Fo2) + (0.0991P)2 + 5.3522P]
where P = (Fo2 + 2Fc2)/3
3783 reflections(Δ/σ)max < 0.001
310 parametersΔρmax = 0.96 e Å3
0 restraintsΔρmin = 0.95 e Å3
Crystal data top
C29H31NO8·CHCl3V = 2946.2 (5) Å3
Mr = 640.92Z = 4
Orthorhombic, PnmaMo Kα radiation
a = 16.7247 (18) ŵ = 0.36 mm1
b = 15.7070 (16) ÅT = 100 K
c = 11.2154 (11) Å0.60 × 0.60 × 0.27 mm
Data collection top
Bruker AXS SMART APEX CCD
diffractometer
3783 independent reflections
Absorption correction: multi-scan
Apex2 v2.1-4 (Bruker, 2007)
2924 reflections with I > 2σ(I)
Tmin = 0.768, Tmax = 0.906Rint = 0.031
19031 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0770 restraints
wR(F2) = 0.222H-atom parameters constrained
S = 1.04Δρmax = 0.96 e Å3
3783 reflectionsΔρmin = 0.95 e Å3
310 parameters
Special details top

Experimental. The whole molecule is disordered across a mirror plane in a 1:1 ratio. Only modest restraints were necessary to achieve a stable and meaningful refinement: C atoms C5, 12 and 13 were set to have the same ADPs as their mirror related counterparts, and C5 was also restrained to be isotropic within a standard deviation of 0.001.

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) top
xyzUiso*/UeqOcc. (<1)
N10.9494 (3)0.2721 (3)0.1879 (4)0.0206 (11)0.50
C10.9456 (3)0.1835 (4)0.1743 (5)0.0244 (12)0.50
O41.0028 (3)0.1368 (4)0.1908 (5)0.0362 (11)0.50
C171.0161 (3)0.3174 (4)0.2306 (4)0.0244 (9)0.50
O51.0161 (3)0.3940 (3)0.2221 (5)0.0333 (11)0.50
C181.0827 (3)0.2688 (4)0.2904 (5)0.0319 (18)0.50
H18A1.11480.23950.22980.048*0.50
H18B1.05990.22680.34530.048*0.50
H18C1.11670.30840.33490.048*0.50
C20.8662 (5)0.1481 (4)0.1368 (7)0.0217 (14)0.50
C30.8556 (6)0.1304 (6)0.0162 (7)0.0255 (16)0.50
H30.89600.14530.03950.031*0.50
C40.7864 (6)0.0914 (6)0.0224 (10)0.031 (2)0.50
C50.7270 (4)0.0713 (5)0.0581 (8)0.0259 (12)0.50
C60.7367 (6)0.0891 (10)0.1793 (15)0.028 (2)0.50
H60.69560.07500.23430.034*0.50
C70.8065 (8)0.1276 (8)0.2192 (13)0.024 (2)0.50
C80.8197 (9)0.1427 (8)0.3523 (15)0.026 (2)0.50
H8A0.87430.16580.36360.032*0.50
H8B0.81730.08720.39370.032*0.50
C120.730 (2)0.1103 (18)0.2070 (13)0.060 (2)0.50
H12A0.67950.07800.21050.090*0.50
H12B0.75060.11810.28780.090*0.50
H12C0.71950.16610.17080.090*0.50
C130.6094 (11)0.0167 (13)0.1043 (17)0.0661 (18)0.50
H13A0.63250.02460.16000.099*0.50
H13B0.55910.00570.07240.099*0.50
H13C0.59910.07040.14630.099*0.50
O10.7819 (6)0.0686 (6)0.1425 (8)0.061 (3)0.50
O20.6615 (4)0.0308 (5)0.0134 (8)0.0418 (16)0.50
C2A0.8822 (4)0.3234 (4)0.1490 (6)0.0181 (13)0.50
C3A0.8764 (5)0.3434 (5)0.0285 (8)0.0218 (14)0.50
H3A0.91650.32480.02550.026*0.50
C4A0.8125 (5)0.3898 (6)0.0125 (8)0.0219 (17)0.50
C5A0.7533 (4)0.4186 (4)0.0663 (8)0.0259 (12)0.50
C6A0.7599 (6)0.3984 (8)0.1855 (11)0.020 (2)0.50
H6A0.71980.41750.23920.025*0.50
C7A0.8236 (8)0.3508 (7)0.2294 (13)0.0204 (19)0.50
C8A0.8300 (10)0.3349 (8)0.3635 (14)0.028 (3)0.50
H8AA0.87680.29800.37920.034*0.50
H8BA0.83920.38990.40440.034*0.50
C12A0.746 (2)0.3756 (19)0.2019 (14)0.060 (2)0.50
H12D0.69470.39830.17590.090*0.50
H12E0.74700.31370.19130.090*0.50
H12F0.75480.38940.28620.090*0.50
C13A0.6203 (12)0.5015 (15)0.0823 (19)0.0661 (18)0.50
H13D0.63880.54210.14270.099*0.50
H13E0.58990.45590.12090.099*0.50
H13F0.58610.53100.02470.099*0.50
O1A0.8093 (4)0.4132 (5)0.1316 (6)0.0332 (13)0.50
O2A0.6922 (3)0.4636 (5)0.0180 (7)0.0344 (14)0.50
C90.75798 (15)0.2056 (2)0.4143 (2)0.0313 (6)
C100.69566 (15)0.16229 (17)0.4709 (2)0.0286 (5)
H100.69590.10180.47130.034*
C110.63341 (14)0.20512 (16)0.5266 (2)0.0238 (5)
C140.56729 (17)0.07598 (16)0.5819 (2)0.0320 (6)
H14A0.56470.05670.49890.048*
H14B0.51960.05650.62480.048*
H14C0.61520.05240.62000.048*
C151.0006 (3)0.25000.6738 (4)0.0420 (10)
H151.01740.25000.75930.050*
Cl11.03797 (9)0.15911 (7)0.60455 (10)0.0796 (4)
Cl20.89488 (11)0.25000.6660 (2)0.1029 (7)
O30.57083 (11)0.16755 (11)0.58510 (15)0.0271 (4)
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
N10.0215 (18)0.020 (3)0.0201 (19)0.0030 (16)0.0019 (13)0.0025 (15)
C10.033 (3)0.024 (3)0.016 (2)0.004 (3)0.0006 (18)0.003 (2)
O40.032 (2)0.028 (3)0.049 (3)0.010 (2)0.005 (2)0.005 (2)
C170.028 (2)0.026 (3)0.019 (2)0.003 (2)0.0008 (18)0.000 (2)
O50.034 (2)0.027 (3)0.040 (3)0.006 (2)0.0076 (19)0.002 (2)
C180.028 (2)0.044 (6)0.024 (2)0.000 (2)0.0027 (16)0.003 (2)
C20.025 (3)0.016 (3)0.024 (3)0.003 (3)0.005 (2)0.002 (3)
C30.031 (5)0.028 (4)0.018 (3)0.005 (3)0.002 (3)0.000 (3)
C40.046 (6)0.026 (4)0.022 (3)0.002 (4)0.013 (4)0.005 (3)
C50.022 (4)0.0256 (17)0.0302 (18)0.0005 (14)0.012 (3)0.0001 (18)
C60.018 (5)0.033 (5)0.034 (3)0.006 (4)0.003 (4)0.006 (3)
C70.031 (7)0.023 (5)0.019 (4)0.000 (4)0.003 (4)0.002 (4)
C80.021 (4)0.037 (6)0.021 (4)0.008 (4)0.001 (3)0.004 (4)
C120.090 (11)0.056 (8)0.034 (2)0.003 (4)0.008 (3)0.009 (4)
C130.104 (5)0.053 (8)0.041 (6)0.009 (4)0.004 (5)0.007 (3)
O10.110 (7)0.047 (4)0.025 (3)0.003 (4)0.029 (4)0.009 (3)
O20.044 (4)0.035 (3)0.046 (3)0.017 (4)0.015 (4)0.003 (2)
C2A0.023 (3)0.016 (3)0.016 (2)0.002 (2)0.002 (2)0.002 (2)
C3A0.020 (3)0.024 (4)0.021 (3)0.002 (3)0.000 (2)0.000 (3)
C4A0.021 (4)0.028 (5)0.016 (4)0.003 (3)0.000 (3)0.003 (3)
C5A0.022 (4)0.0256 (17)0.0302 (18)0.0005 (14)0.012 (3)0.0001 (18)
C6A0.016 (5)0.027 (4)0.018 (3)0.004 (4)0.003 (4)0.002 (3)
C7A0.024 (5)0.020 (5)0.017 (3)0.005 (3)0.003 (3)0.000 (4)
C8A0.040 (6)0.034 (6)0.011 (4)0.003 (4)0.001 (3)0.002 (4)
C12A0.090 (11)0.056 (8)0.034 (2)0.003 (4)0.008 (3)0.009 (4)
C13A0.104 (5)0.053 (8)0.041 (6)0.009 (4)0.004 (5)0.007 (3)
O1A0.042 (3)0.043 (4)0.014 (2)0.005 (2)0.001 (2)0.013 (2)
O2A0.026 (3)0.045 (3)0.032 (3)0.014 (3)0.001 (3)0.000 (2)
C90.0278 (11)0.0524 (16)0.0138 (10)0.0080 (11)0.0019 (9)0.0029 (10)
C100.0354 (13)0.0343 (13)0.0161 (10)0.0086 (10)0.0003 (9)0.0036 (9)
C110.0284 (11)0.0287 (12)0.0144 (10)0.0009 (9)0.0020 (8)0.0018 (9)
C140.0437 (14)0.0218 (11)0.0306 (13)0.0003 (10)0.0003 (11)0.0008 (10)
C150.049 (2)0.048 (2)0.0291 (19)0.0000.0080 (18)0.000
Cl10.1294 (11)0.0593 (6)0.0501 (6)0.0216 (6)0.0083 (6)0.0069 (5)
Cl20.0524 (9)0.1380 (19)0.1183 (17)0.0000.0117 (10)0.000
O30.0349 (9)0.0215 (8)0.0248 (8)0.0003 (7)0.0055 (7)0.0008 (6)
Geometric parameters (Å, º) top
N1—C11.401 (10)C3A—H3A0.9500
N1—C171.408 (7)C4A—O1A1.386 (11)
N1—C2A1.450 (7)C4A—C5A1.403 (12)
C1—O41.220 (8)C5A—O2A1.356 (7)
C1—C21.500 (8)C5A—C6A1.378 (16)
C17—O51.208 (7)C6A—C7A1.391 (10)
C17—C181.507 (7)C6A—H6A0.9500
C18—H18A0.9800C7A—C8A1.528 (19)
C18—H18B0.9800C8A—C9i1.476 (18)
C18—H18C0.9800C8A—H8AA0.9900
C2—C31.392 (11)C8A—H8BA0.9900
C2—C71.398 (17)C12A—O1A1.44 (4)
C3—C41.379 (10)C12A—H12D0.9800
C3—H30.9500C12A—H12E0.9800
C4—C51.379 (14)C12A—H12F0.9800
C4—O11.395 (13)C13A—O2A1.52 (3)
C5—O21.364 (7)C13A—H13D0.9800
C5—C61.40 (2)C13A—H13E0.9800
C6—C71.388 (11)C13A—H13F0.9800
C6—H60.9500C9—C9i1.396 (6)
C7—C81.53 (2)C9—C101.397 (4)
C8—C91.589 (15)C9—C8Ai1.476 (18)
C8—H8A0.9900C10—C111.388 (3)
C8—H8B0.9900C10—H100.9500
C12—O11.31 (4)C11—O31.369 (3)
C12—H12A0.9800C11—C11i1.410 (5)
C12—H12B0.9800C14—O31.440 (3)
C12—H12C0.9800C14—H14A0.9800
C13—O21.36 (3)C14—H14B0.9800
C13—H13A0.9800C14—H14C0.9800
C13—H13B0.9800C15—Cl11.741 (3)
C13—H13C0.9800C15—Cl1i1.741 (3)
C2A—C3A1.391 (11)C15—Cl21.771 (5)
C2A—C7A1.400 (16)C15—H151.0000
C3A—C4A1.372 (9)
C1—N1—C17125.1 (5)O1A—C4A—C5A119.6 (8)
C1—N1—C2A119.0 (5)O2A—C5A—C6A124.7 (8)
C17—N1—C2A115.8 (5)O2A—C5A—C4A116.6 (8)
O4—C1—N1123.0 (6)C6A—C5A—C4A118.7 (7)
O4—C1—C2121.0 (7)C5A—C6A—C7A122.0 (9)
N1—C1—C2116.0 (5)C5A—C6A—H6A119.0
O5—C17—N1118.5 (5)C7A—C6A—H6A119.0
O5—C17—C18122.7 (5)C6A—C7A—C2A118.2 (10)
N1—C17—C18118.8 (5)C6A—C7A—C8A119.3 (11)
C3—C2—C7120.3 (8)C2A—C7A—C8A122.4 (10)
C3—C2—C1117.3 (7)C9i—C8A—C7A113.1 (12)
C7—C2—C1122.2 (8)C9i—C8A—H8AA109.0
C4—C3—C2120.1 (8)C7A—C8A—H8AA109.0
C4—C3—H3120.0C9i—C8A—H8BA109.0
C2—C3—H3120.0C7A—C8A—H8BA109.0
C5—C4—C3120.0 (9)H8AA—C8A—H8BA107.8
C5—C4—O1122.3 (8)C4A—O1A—C12A116.6 (10)
C3—C4—O1117.5 (9)C5A—O2A—C13A127.5 (8)
O2—C5—C4116.4 (8)C9i—C9—C10119.12 (16)
O2—C5—C6123.0 (8)C9i—C9—C8Ai115.5 (5)
C4—C5—C6120.5 (7)C10—C9—C8Ai125.0 (6)
C7—C6—C5119.8 (10)C9i—C9—C8128.4 (5)
C7—C6—H6120.1C10—C9—C8112.4 (6)
C5—C6—H6120.1C11—C10—C9121.9 (2)
C6—C7—C2119.2 (10)C11—C10—H10119.1
C6—C7—C8120.3 (12)C9—C10—H10119.1
C2—C7—C8120.4 (10)O3—C11—C10125.5 (2)
C7—C8—C9115.5 (11)O3—C11—C11i115.54 (12)
C7—C8—H8A108.4C10—C11—C11i118.99 (15)
C9—C8—H8A108.4O3—C14—H14A109.5
C7—C8—H8B108.4O3—C14—H14B109.5
C9—C8—H8B108.4H14A—C14—H14B109.5
H8A—C8—H8B107.5O3—C14—H14C109.5
C12—O1—C4116.1 (13)H14A—C14—H14C109.5
C13—O2—C5108.3 (9)H14B—C14—H14C109.5
C3A—C2A—C7A120.5 (7)Cl1—C15—Cl1i110.2 (3)
C3A—C2A—N1118.2 (6)Cl1—C15—Cl2109.66 (18)
C7A—C2A—N1121.3 (7)Cl1i—C15—Cl2109.66 (18)
C4A—C3A—C2A120.0 (7)Cl1—C15—H15109.1
C4A—C3A—H3A120.0Cl1i—C15—H15109.1
C2A—C3A—H3A120.0Cl2—C15—H15109.1
C3A—C4A—O1A119.6 (7)C11—O3—C14116.8 (2)
C3A—C4A—C5A120.7 (7)
C17—N1—C1—O45.3 (9)C17—N1—C2A—C3A94.9 (7)
C2A—N1—C1—O4170.6 (6)C1—N1—C2A—C7A97.0 (9)
C17—N1—C1—C2175.1 (5)C17—N1—C2A—C7A86.6 (9)
C2A—N1—C1—C28.9 (9)C7A—C2A—C3A—C4A0.3 (12)
C1—N1—C17—O5169.5 (5)N1—C2A—C3A—C4A178.2 (7)
C2A—N1—C17—O56.6 (7)C2A—C3A—C4A—O1A176.6 (8)
C1—N1—C17—C1813.5 (7)C2A—C3A—C4A—C5A0.8 (12)
C2A—N1—C17—C18170.5 (5)C3A—C4A—C5A—O2A179.6 (7)
O4—C1—C2—C381.8 (8)O1A—C4A—C5A—O2A4.6 (12)
N1—C1—C2—C397.8 (8)C3A—C4A—C5A—C6A0.8 (13)
O4—C1—C2—C793.7 (10)O1A—C4A—C5A—C6A176.6 (9)
N1—C1—C2—C786.7 (10)O2A—C5A—C6A—C7A179.0 (10)
C7—C2—C3—C40.9 (14)C4A—C5A—C6A—C7A0.3 (15)
C1—C2—C3—C4174.7 (8)C5A—C6A—C7A—C2A0.2 (17)
C2—C3—C4—C51.3 (14)C5A—C6A—C7A—C8A176.5 (12)
C2—C3—C4—O1174.6 (8)C3A—C2A—C7A—C6A0.2 (15)
C3—C4—C5—O2178.3 (8)N1—C2A—C7A—C6A178.7 (8)
O1—C4—C5—O22.6 (14)C3A—C2A—C7A—C8A176.4 (10)
C3—C4—C5—C60.9 (15)N1—C2A—C7A—C8A5.2 (16)
O1—C4—C5—C6174.8 (11)C6A—C7A—C8A—C9i56.0 (14)
O2—C5—C6—C7177.4 (10)C2A—C7A—C8A—C9i127.9 (11)
C4—C5—C6—C70.2 (17)C3A—C4A—O1A—C12A113.7 (10)
C5—C6—C7—C20.1 (19)C5A—C4A—O1A—C12A70.5 (12)
C5—C6—C7—C8176.5 (13)C6A—C5A—O2A—C13A0.9 (17)
C3—C2—C7—C60.2 (17)C4A—C5A—O2A—C13A179.6 (12)
C1—C2—C7—C6175.2 (10)C7—C8—C9—C9i80.9 (9)
C3—C2—C7—C8176.8 (10)C7—C8—C9—C1096.6 (10)
C1—C2—C7—C81.4 (17)C7—C8—C9—C8Ai113 (5)
C6—C7—C8—C963.1 (15)C9i—C9—C10—C110.4 (3)
C2—C7—C8—C9120.3 (12)C8Ai—C9—C10—C11173.7 (7)
C5—C4—O1—C1271.5 (13)C8—C9—C10—C11177.4 (6)
C3—C4—O1—C12112.7 (12)C9—C10—C11—O3179.2 (2)
C4—C5—O2—C13179.6 (11)C9—C10—C11—C11i0.4 (3)
C6—C5—O2—C133.1 (15)C10—C11—O3—C144.0 (3)
C1—N1—C2A—C3A81.5 (8)C11i—C11—O3—C14177.25 (15)
Symmetry code: (i) x, y+1/2, z.
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
C3A—H3A···O3ii0.952.673.497 (8)146
C13—H13C···O5iii0.982.102.862 (15)133
C13A—H13E···O4iii0.982.953.880 (13)159
C14—H14A···O4iv0.982.683.381 (7)129
C13A—H13E···O5iv0.982.363.271 (14)155
C13—H13C···O4iv0.982.653.466 (14)141
C18—H18C···C6Av0.982.793.606 (13)141
C15—H15···O3vi1.002.353.220 (4)145
C15—H15···O3vii1.002.353.220 (4)145
C12A—H12D···O2A0.982.402.968 (19)116
C18—H18A···Cg1viii0.982.633.496148
C18—H18A···Cg1ix0.982.633.496148
Symmetry codes: (ii) x+1/2, y+1/2, z+1/2; (iii) x1/2, y+1/2, z+1/2; (iv) x1/2, y, z+1/2; (v) x+1/2, y, z+1/2; (vi) x+1/2, y, z+3/2; (vii) x+1/2, y+1/2, z+3/2; (viii) x, y+1/2, z; (ix) x1/2, y, z1/2.

Experimental details

Crystal data
Chemical formulaC29H31NO8·CHCl3
Mr640.92
Crystal system, space groupOrthorhombic, Pnma
Temperature (K)100
a, b, c (Å)16.7247 (18), 15.7070 (16), 11.2154 (11)
V3)2946.2 (5)
Z4
Radiation typeMo Kα
µ (mm1)0.36
Crystal size (mm)0.60 × 0.60 × 0.27
Data collection
DiffractometerBruker AXS SMART APEX CCD
diffractometer
Absorption correctionMulti-scan
Apex2 v2.1-4 (Bruker, 2007)
Tmin, Tmax0.768, 0.906
No. of measured, independent and
observed [I > 2σ(I)] reflections
19031, 3783, 2924
Rint0.031
(sin θ/λ)max1)0.667
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.077, 0.222, 1.04
No. of reflections3783
No. of parameters310
H-atom treatmentH-atom parameters constrained
Δρmax, Δρmin (e Å3)0.96, 0.95

Computer programs: Apex2 v2.1-4 (Bruker, 2007), Apex2 v2.1-4, SHELXTL 6.14 (Bruker, 2000-2003), SHELXTL 6.14.

Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
C3A—H3A···O3i0.952.673.497 (8)146.1
C13—H13C···O5ii0.982.102.862 (15)133.0
C13A—H13E···O4ii0.982.953.880 (13)159.1
C14—H14A···O4iii0.982.683.381 (7)128.8
C13A—H13E···O5iii0.982.363.271 (14)154.5
C13—H13C···O4iii0.982.653.466 (14)140.9
C18—H18C···C6Aiv0.982.793.606 (13)141.1
C15—H15···O3v1.002.353.220 (4)145.0
C15—H15···O3vi1.002.353.220 (4)145.0
C12A—H12D···O2A0.982.402.968 (19)116.0
C18—H18A···Cg1vii0.982.633.496147.65
C18—H18A···Cg1viii0.982.633.496147.65
Symmetry codes: (i) x+1/2, y+1/2, z+1/2; (ii) x1/2, y+1/2, z+1/2; (iii) x1/2, y, z+1/2; (iv) x+1/2, y, z+1/2; (v) x+1/2, y, z+3/2; (vi) x+1/2, y+1/2, z+3/2; (vii) x, y+1/2, z; (viii) x1/2, y, z1/2.
 

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