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ISSN: 2056-9890

4′-(4-Fluoro­phen­yl)-1′-methyl­di­spiro­[indane-2,2′-pyrrolidine-3′,2′′-indane]-1,3,1′′-trione methanol hemisolvate

aInstitute for Research in Molecular Medicine, Universiti Sains Malaysia, 11800 USM, Penang, Malaysia, bFaculty of Pharmaceutical Science, UCSI (University College Sedaya International) University, Kuala Lumpur, Malaysia, and cX-ray Crystallography Unit, School of Physics, Universiti Sains Malaysia, 11800 USM, Penang, Malaysia
*Correspondence e-mail: arazaki@usm.my

(Received 8 March 2013; accepted 11 April 2013; online 17 April 2013)

The asymmetric unit of the title compound, C29H24FNO5·0.5CH3OH, contains two independent mol­ecules and a one methanol solvent mol­ecule. The methanol mol­ecule is O—H⋯O hydrogen bonded to one of the independent mol­ecules. The pyrrolidine rings in both mol­ecules adopt half-chair conformations, while the cyclo­pentane rings within the indane groups are in flattened envelope conformations, with the spiro C atoms forming the flaps. The benzene rings of the indane ring systems form a dihedral angle of 35.06 (7)° in one independent mol­ecule and 31.16 (8)° in the other. The fluoro-substituted benzene ring forms dihedral angles of 65.35 (6) and 85.87 (7)° with the indane group benzene rings in one mol­ecule, and 72.78 (8) and 77.27 (8)° in the other. In each mol­ecule, a weak intra­molecular C—H⋯O hydrogen bond forms an S(6) ring motif. In the crystal, weak C—H⋯O, C—H⋯N and C—H⋯F hydrogen bonds link the mol­ecules into a three-dimensional network.

Related literature

For background to compounds with anti­tubercular activity, see: Ali et al. (2011[Ali, M. A., Ismail, R., Choon, T. S., Pandian, S. & Ansari, M. Z. H. (2011). J. Enzyme Inhib. Med. Chem. 26, 598-602.]). For related structures, see: Wei et al. (2011[Wei, A. C., Ali, M. A., Yoon, Y. K., Quah, C. K. & Fun, H.-K. (2011). Acta Cryst. E67, o3274.], 2012[Wei, A. C., Ali, M. A., Choon, T. S., Arshad, S. & Razak, I. A. (2012). Acta Cryst. E68, o1265-o1266.]). For hydrogen-bond motifs, see: Bernstein et al. (1995[Bernstein, J., Davis, R. E., Shimoni, L. & Chang, N.-L. (1995). Angew. Chem. Int. Ed. Engl. 34, 1555-1573.]). For ring conformations, see: Cremer & Pople (1975[Cremer, D. & Pople, J. A. (1975). J. Am. Chem. Soc. 97, 1354-1358.]). For the stability of the temperature controller used in the data collection, see: Cosier & Glazer (1986[Cosier, J. & Glazer, A. M. (1986). J. Appl. Cryst. 19, 105-107.]).

[Scheme 1]

Experimental

Crystal data
  • C29H24FNO5·0.5CH4O

  • Mr = 501.52

  • Monoclinic, P 21 /c

  • a = 14.6385 (6) Å

  • b = 12.5099 (6) Å

  • c = 26.2017 (10) Å

  • β = 92.645 (1)°

  • V = 4793.1 (4) Å3

  • Z = 8

  • Mo Kα radiation

  • μ = 0.10 mm−1

  • T = 100 K

  • 0.44 × 0.21 × 0.15 mm

Data collection
  • Bruker APEX DUO CCD area-detector diffractometer

  • Absorption correction: multi-scan (SADABS; Bruker, 2009[Bruker (2009). APEX2, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.]) Tmin = 0.957, Tmax = 0.985

  • 53390 measured reflections

  • 14094 independent reflections

  • 10283 reflections with I > 2σ(I)

  • Rint = 0.046

Refinement
  • R[F2 > 2σ(F2)] = 0.049

  • wR(F2) = 0.147

  • S = 1.04

  • 14094 reflections

  • 678 parameters

  • H atoms treated by a mixture of independent and constrained refinement

  • Δρmax = 0.40 e Å−3

  • Δρmin = −0.27 e Å−3

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A D—H H⋯A DA D—H⋯A
O6—H1O6⋯O4A 0.97 (3) 1.99 (3) 2.9346 (18) 164 (3)
C8A—H8AA⋯O5A 0.99 2.43 3.088 (2) 124
C8B—H8BA⋯O5B 0.99 2.38 3.0960 (19) 128
C26A—H26A⋯O5Ai 0.95 2.54 3.2430 (18) 131
C27A—H27A⋯N1Bii 0.98 2.42 3.337 (2) 155
C28A—H28A⋯O2Biii 0.98 2.50 3.3478 (19) 145
C28B—H28F⋯O6iv 0.98 2.46 3.360 (2) 153
C30—H30B⋯F1Av 0.98 2.53 3.307 (2) 136
Symmetry codes: (i) -x+1, -y+2, -z+2; (ii) [-x+2, y+{\script{1\over 2}}, -z+{\script{3\over 2}}]; (iii) -x+2, -y+2, -z+2; (iv) x+1, y, z; (v) -x+1, -y+1, -z+2.

Data collection: APEX2 (Bruker, 2009[Bruker (2009). APEX2, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.]); cell refinement: SAINT (Bruker, 2009[Bruker (2009). APEX2, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.]); data reduction: SAINT; program(s) used to solve structure: SHELXTL (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL and PLATON (Spek, 2009[Spek, A. L. (2009). Acta Cryst. D65, 148-155.]).

Supporting information


Comment top

Tuberculosis (TB) remains a global health problem and has infected about one third of the world population. No new drugs have been discovered for the past 40 years and therefore new anti-TB agents are desperately needed (Ali et al., 2011). As part of our ongoing search for novel heterocyclic compounds with antitubercular activity (Wei et al., 2011, 2012) the crystal structure of the title compound (I) has been determined.

The asymmetric unit of the title compound (Fig. 1) contains two crystallographically independent molecules and a molecule of methanol (Fig. 1). In both molecules, the intramolecular interactions of C8A—H8AA···O5A and C8B—H8BA···O5B (Table 1) form an S(6) ring motif (Fig. 2) (Bernstein et al. 1995). The pyrrolidine ring for both molecules A and B adopt a half-chair conformation with the puckering parameters Q = 0.4612 (16) Å, φ = 127.36 (19)° for molecule A and Q = 0.4332 (16) Å, φ = 125.2 (2)° for molecule B. In both molecules, A and B, the cyclopentane rings (C1—C2/C7—C9 & C12—C14/C19—C20) within the indane moiety (C1—C9 & C12—C20) form flattened envelope conformations (C9 and C12 at the flap) with the puckering parameters Q = 0.1587 (16) Å, φ 146.2 (6)° and Q = 0.1910 (16) Å, φ = 175.0 (5)° for molecule A and Q = 0.1338 (15)å, φ = 155.5 (6)° and Q = 0.2232 (16) Å, φ = 173.6 (4)° for molecule B.

In each molecule, the benzene rings of the indane ring systems form dihedral angles of 35.06 (7) ° [C2A-C7A/C14A-C19A] and 31.16 (8)° [C2B-C7B/C14B-C19B] with each other. The fluoro-substituted benzene ring forms diedral angles of 65.35 (6)° [C14A-C19A/C21A-C26A] and 85.87 (7)° [C2A-C7A/C21A-C26A] with the indane group benzene rings of one molecule and 72.78 (8)° [C14B-C19B/C21B-C26B] and 77.27 (8)° [C2B-C7B/C21B-C26B] in the other.

In the crystal, molecules are connected by weak C—H···Oi, iii, iv, C—H···Nii and C—H···Fv (Table 1) hydrogen bonds into a three-dimensional network (Fig. 3).

Related literature top

For background to compounds with antitubercular activity, see: Ali et al. (2011). For related structures, see: Wei et al. (2011, 2012). For hydrogen-bond motifs, see: Bernstein et al. (1995). For ring conformations, see: Cremer & Pople (1975). For the stability of the temperature controller used in the data collection, see: Cosier & Glazer (1986).

Experimental top

A mixture of 5,6-dimethoxy(E)-2-(4-fluorobenzylidene)-2,3-dihydro-1H-indene-1-one (0.001 mol), ninhydrin (0.001 mol) and sarcosine (0.002 mol) (1:1:2) were dissolved in methanol (10 ml) and refluxed for 4 h. After completion of the reaction as evident from TLC, the excess solvent was evaporated slowly and the product was separated and recrystallized from methanol to reveal the title compound as yellow crystals.

Refinement top

O bound H atoms were located from a difference Fourier maps and freely refined. The remaining H atoms were positioned geometrically and refined using a riding model with C—H = 0.95–1.00 Å and Uiso(H) = 1.2Ueq(C) and 1.5Ueq(C-methyl).

Structure description top

Tuberculosis (TB) remains a global health problem and has infected about one third of the world population. No new drugs have been discovered for the past 40 years and therefore new anti-TB agents are desperately needed (Ali et al., 2011). As part of our ongoing search for novel heterocyclic compounds with antitubercular activity (Wei et al., 2011, 2012) the crystal structure of the title compound (I) has been determined.

The asymmetric unit of the title compound (Fig. 1) contains two crystallographically independent molecules and a molecule of methanol (Fig. 1). In both molecules, the intramolecular interactions of C8A—H8AA···O5A and C8B—H8BA···O5B (Table 1) form an S(6) ring motif (Fig. 2) (Bernstein et al. 1995). The pyrrolidine ring for both molecules A and B adopt a half-chair conformation with the puckering parameters Q = 0.4612 (16) Å, φ = 127.36 (19)° for molecule A and Q = 0.4332 (16) Å, φ = 125.2 (2)° for molecule B. In both molecules, A and B, the cyclopentane rings (C1—C2/C7—C9 & C12—C14/C19—C20) within the indane moiety (C1—C9 & C12—C20) form flattened envelope conformations (C9 and C12 at the flap) with the puckering parameters Q = 0.1587 (16) Å, φ 146.2 (6)° and Q = 0.1910 (16) Å, φ = 175.0 (5)° for molecule A and Q = 0.1338 (15)å, φ = 155.5 (6)° and Q = 0.2232 (16) Å, φ = 173.6 (4)° for molecule B.

In each molecule, the benzene rings of the indane ring systems form dihedral angles of 35.06 (7) ° [C2A-C7A/C14A-C19A] and 31.16 (8)° [C2B-C7B/C14B-C19B] with each other. The fluoro-substituted benzene ring forms diedral angles of 65.35 (6)° [C14A-C19A/C21A-C26A] and 85.87 (7)° [C2A-C7A/C21A-C26A] with the indane group benzene rings of one molecule and 72.78 (8)° [C14B-C19B/C21B-C26B] and 77.27 (8)° [C2B-C7B/C21B-C26B] in the other.

In the crystal, molecules are connected by weak C—H···Oi, iii, iv, C—H···Nii and C—H···Fv (Table 1) hydrogen bonds into a three-dimensional network (Fig. 3).

For background to compounds with antitubercular activity, see: Ali et al. (2011). For related structures, see: Wei et al. (2011, 2012). For hydrogen-bond motifs, see: Bernstein et al. (1995). For ring conformations, see: Cremer & Pople (1975). For the stability of the temperature controller used in the data collection, see: Cosier & Glazer (1986).

Computing details top

Data collection: APEX2 (Bruker, 2009); cell refinement: SAINT (Bruker, 2009); data reduction: SAINT (Bruker, 2009); program(s) used to solve structure: SHELXTL (Sheldrick, 2008); program(s) used to refine structure: SHELXTL (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXTL (Sheldrick, 2008) and PLATON (Spek, 2009).

Figures top
[Figure 1] Fig. 1. Molecule A of the title compound, showing 50% probability displacement ellipsoids. The dashed lines indicate hydrogen bonds. The solvent molecule is also shown.
[Figure 2] Fig. 2. Molecule B of the title compound, showing 50% probability displacement ellipsoids. The dashed line indicates a weak hydrogen bond.
[Figure 3] Fig. 3. The crystal packing of (I). Dashed lines indicate hydrogen bonds. H atoms not involved in the hydrogen bond interactions have been omitted for clarity.
4'-(4-Fluorophenyl)-1'-methyldispiro[indan-2,2'-pyrrolidine-3',2''-indan]-1,3,1''-trione methanol hemisolvate top
Crystal data top
C29H24FNO5·0.5CH4OF(000) = 2104
Mr = 501.52Dx = 1.390 Mg m3
Monoclinic, P21/cMo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybcCell parameters from 9905 reflections
a = 14.6385 (6) Åθ = 2.3–30.1°
b = 12.5099 (6) ŵ = 0.10 mm1
c = 26.2017 (10) ÅT = 100 K
β = 92.645 (1)°Block, yellow
V = 4793.1 (4) Å30.44 × 0.21 × 0.15 mm
Z = 8
Data collection top
Bruker APEX DUO CCD area-detector
diffractometer
14094 independent reflections
Radiation source: fine-focus sealed tube10283 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.046
φ and ω scansθmax = 30.2°, θmin = 1.4°
Absorption correction: multi-scan
(SADABS; Bruker, 2009)
h = 2019
Tmin = 0.957, Tmax = 0.985k = 1717
53390 measured reflectionsl = 3737
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)] = 0.049Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.147H atoms treated by a mixture of independent and constrained refinement
S = 1.04 w = 1/[σ2(Fo2) + (0.0784P)2 + 0.9156P]
where P = (Fo2 + 2Fc2)/3
14094 reflections(Δ/σ)max = 0.001
678 parametersΔρmax = 0.40 e Å3
0 restraintsΔρmin = 0.27 e Å3
Crystal data top
C29H24FNO5·0.5CH4OV = 4793.1 (4) Å3
Mr = 501.52Z = 8
Monoclinic, P21/cMo Kα radiation
a = 14.6385 (6) ŵ = 0.10 mm1
b = 12.5099 (6) ÅT = 100 K
c = 26.2017 (10) Å0.44 × 0.21 × 0.15 mm
β = 92.645 (1)°
Data collection top
Bruker APEX DUO CCD area-detector
diffractometer
14094 independent reflections
Absorption correction: multi-scan
(SADABS; Bruker, 2009)
10283 reflections with I > 2σ(I)
Tmin = 0.957, Tmax = 0.985Rint = 0.046
53390 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0490 restraints
wR(F2) = 0.147H atoms treated by a mixture of independent and constrained refinement
S = 1.04Δρmax = 0.40 e Å3
14094 reflectionsΔρmin = 0.27 e Å3
678 parameters
Special details top

Experimental. The crystal was placed in the cold stream of an Oxford Cryosystems Cobra open-flow nitrogen cryostat (Cosier & Glazer, 1986) operating at 100.0 (1) K.

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*/Ueq
F1A0.64124 (8)0.50699 (10)1.07056 (4)0.0408 (3)
O1A0.57712 (7)0.75263 (10)0.83001 (4)0.0224 (2)
O2A0.90976 (7)0.94421 (10)0.81133 (4)0.0217 (2)
O3A0.92179 (7)1.05466 (10)0.89424 (4)0.0230 (2)
O4A0.36455 (7)0.82926 (10)0.82207 (4)0.0235 (2)
O5A0.52744 (8)1.12958 (10)0.87961 (4)0.0297 (3)
N1A0.40617 (8)0.96181 (12)0.91618 (4)0.0213 (3)
C1A0.60138 (9)0.82167 (13)0.86036 (5)0.0169 (3)
C2A0.68848 (9)0.87866 (12)0.86443 (5)0.0159 (3)
C3A0.75949 (9)0.87575 (13)0.83026 (5)0.0166 (3)
H3AA0.75490.83250.80050.020*
C4A0.83602 (9)0.93716 (13)0.84103 (5)0.0170 (3)
C5A0.84241 (9)0.99947 (13)0.88693 (5)0.0179 (3)
C6A0.77115 (9)1.00136 (13)0.92012 (5)0.0190 (3)
H6AA0.77561.04290.95050.023*
C7A0.69312 (9)0.94131 (13)0.90805 (5)0.0168 (3)
C8A0.60674 (9)0.93285 (14)0.93741 (5)0.0199 (3)
H8AA0.58201.00460.94490.024*
H8AB0.61830.89390.96990.024*
C9A0.54029 (9)0.86988 (13)0.90093 (5)0.0177 (3)
C10A0.47557 (9)0.78925 (13)0.92612 (5)0.0186 (3)
H10A0.45090.74140.89820.022*
C11A0.39533 (10)0.85875 (14)0.94223 (5)0.0230 (3)
H11A0.33620.82520.93160.028*
H11B0.39760.86860.97980.028*
C12A0.46681 (9)0.94658 (13)0.87478 (5)0.0188 (3)
C13A0.42549 (9)0.89548 (13)0.82479 (5)0.0187 (3)
C14A0.46926 (9)0.94764 (13)0.78149 (5)0.0192 (3)
C15A0.46305 (10)0.92065 (14)0.72959 (5)0.0225 (3)
H15A0.42940.86000.71770.027*
C16A0.50824 (11)0.98630 (15)0.69640 (6)0.0265 (3)
H16A0.50480.97070.66090.032*
C17A0.55860 (11)1.07468 (15)0.71386 (6)0.0283 (4)
H17A0.58881.11770.69000.034*
C18A0.56576 (11)1.10154 (14)0.76558 (6)0.0251 (3)
H18A0.60051.16140.77750.030*
C19A0.51950 (10)1.03640 (13)0.79895 (5)0.0203 (3)
C20A0.50932 (10)1.05031 (14)0.85470 (5)0.0213 (3)
C21A0.52098 (9)0.71733 (13)0.96626 (5)0.0194 (3)
C22A0.56305 (10)0.62396 (14)0.95030 (5)0.0228 (3)
H22A0.56300.60820.91480.027*
C23A0.60491 (11)0.55361 (15)0.98488 (6)0.0280 (3)
H23A0.63380.49050.97350.034*
C24A0.60348 (11)0.57771 (15)1.03629 (6)0.0264 (3)
C25A0.56456 (11)0.66976 (15)1.05385 (6)0.0266 (3)
H25A0.56580.68531.08940.032*
C26A0.52338 (10)0.73952 (14)1.01870 (5)0.0232 (3)
H26A0.49630.80351.03040.028*
C27A0.90161 (11)0.88598 (15)0.76404 (5)0.0241 (3)
H27A0.95850.89270.74600.036*
H27B0.85080.91510.74270.036*
H27C0.89000.81040.77110.036*
C28A0.94184 (11)1.09428 (14)0.94499 (5)0.0241 (3)
H28A1.00311.12620.94680.036*
H28B0.93961.03520.96940.036*
H28C0.89661.14850.95330.036*
C29A0.32106 (11)1.01814 (16)0.90408 (6)0.0301 (4)
H29A0.33441.08730.88850.045*
H29B0.28851.02960.93550.045*
H29C0.28290.97540.88010.045*
F1B0.73958 (9)0.84660 (11)0.64602 (4)0.0508 (3)
O1B0.70176 (7)0.52113 (10)0.86215 (4)0.0209 (2)
O2B0.87193 (7)0.80278 (10)0.99446 (3)0.0214 (2)
O3B1.01505 (7)0.84762 (9)0.94574 (4)0.0201 (2)
O4B0.72154 (7)0.27525 (10)0.83132 (4)0.0265 (2)
O5B1.01994 (7)0.37946 (11)0.87438 (4)0.0271 (3)
N1B0.89700 (8)0.33138 (11)0.78465 (4)0.0196 (3)
C1B0.78116 (9)0.54550 (12)0.85591 (4)0.0152 (3)
C2B0.83736 (9)0.62300 (12)0.88429 (5)0.0147 (3)
C3B0.81686 (9)0.67684 (13)0.92947 (5)0.0163 (3)
H3BA0.76100.66420.94550.020*
C4B0.88014 (9)0.74835 (12)0.94969 (4)0.0162 (3)
C5B0.96145 (9)0.77097 (12)0.92353 (5)0.0163 (3)
C6B0.98171 (9)0.71501 (12)0.87953 (5)0.0161 (3)
H6BA1.03680.72830.86280.019*
C7B0.91913 (9)0.63893 (12)0.86061 (5)0.0147 (3)
C8B0.92686 (9)0.56662 (12)0.81472 (5)0.0162 (3)
H8BA0.98380.52390.81760.019*
H8BB0.92640.60870.78270.019*
C9B0.84145 (9)0.49360 (12)0.81595 (5)0.0152 (3)
C10B0.79019 (9)0.47193 (13)0.76358 (5)0.0171 (3)
H10B0.72750.44670.77130.021*
C11B0.84021 (11)0.37537 (15)0.74183 (5)0.0246 (3)
H11C0.79580.32130.72850.030*
H11D0.87890.39780.71370.030*
C12B0.86621 (9)0.37560 (13)0.83180 (5)0.0168 (3)
C13B0.78331 (10)0.31936 (13)0.85524 (5)0.0195 (3)
C14B0.79773 (10)0.32678 (13)0.91197 (5)0.0217 (3)
C15B0.73581 (12)0.30775 (15)0.94960 (6)0.0293 (4)
H15B0.67580.28240.94130.035*
C16B0.76572 (14)0.32748 (16)1.00007 (6)0.0356 (4)
H16B0.72480.31651.02670.043*
C17B0.85401 (14)0.36275 (16)1.01225 (6)0.0349 (4)
H17B0.87200.37631.04700.042*
C18B0.91653 (12)0.37851 (15)0.97473 (5)0.0285 (4)
H18B0.97760.40020.98310.034*
C19B0.88584 (10)0.36111 (13)0.92418 (5)0.0211 (3)
C20B0.93768 (10)0.37345 (13)0.87703 (5)0.0190 (3)
C21B0.77768 (10)0.57045 (13)0.73034 (5)0.0180 (3)
C22B0.70115 (10)0.63458 (14)0.73650 (5)0.0215 (3)
H22B0.65760.61440.76050.026*
C23B0.68725 (12)0.72781 (15)0.70811 (6)0.0289 (4)
H23B0.63450.77080.71210.035*
C24B0.75230 (13)0.75584 (15)0.67412 (6)0.0332 (4)
C25B0.82992 (12)0.69646 (16)0.66743 (5)0.0303 (4)
H25B0.87390.71870.64410.036*
C26B0.84227 (10)0.60341 (15)0.69561 (5)0.0236 (3)
H26B0.89530.56120.69140.028*
C27B0.80001 (11)0.76736 (16)1.02551 (5)0.0270 (4)
H27D0.80310.80651.05790.041*
H27E0.80690.69061.03220.041*
H27F0.74080.78071.00760.041*
C28B1.09083 (10)0.88541 (14)0.91793 (6)0.0246 (3)
H28D1.11960.94600.93610.037*
H28E1.06900.90820.88370.037*
H28F1.13560.82780.91500.037*
C29B0.91046 (12)0.21643 (14)0.78356 (6)0.0261 (3)
H29D0.94980.19480.81300.039*
H29E0.93950.19650.75200.039*
H29F0.85120.18040.78490.039*
O60.22217 (10)0.69772 (12)0.86621 (5)0.0390 (3)
C300.21176 (13)0.59596 (17)0.84332 (7)0.0352 (4)
H30A0.15910.55950.85720.053*
H30B0.26710.55350.85060.053*
H30C0.20190.60420.80630.053*
H1O60.277 (2)0.733 (3)0.8553 (10)0.072 (9)*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
F1A0.0473 (6)0.0336 (7)0.0402 (5)0.0073 (5)0.0137 (5)0.0095 (5)
O1A0.0207 (5)0.0232 (6)0.0233 (5)0.0028 (4)0.0017 (4)0.0061 (4)
O2A0.0180 (5)0.0276 (7)0.0198 (4)0.0052 (4)0.0042 (3)0.0008 (4)
O3A0.0200 (5)0.0278 (7)0.0209 (4)0.0085 (5)0.0032 (4)0.0018 (4)
O4A0.0189 (5)0.0248 (6)0.0268 (5)0.0033 (5)0.0000 (4)0.0022 (4)
O5A0.0339 (6)0.0223 (7)0.0331 (5)0.0023 (5)0.0060 (5)0.0066 (5)
N1A0.0189 (6)0.0227 (7)0.0229 (5)0.0055 (5)0.0067 (4)0.0016 (5)
C1A0.0153 (6)0.0192 (8)0.0163 (5)0.0008 (6)0.0012 (4)0.0002 (5)
C2A0.0143 (6)0.0167 (7)0.0168 (5)0.0009 (5)0.0003 (4)0.0005 (5)
C3A0.0166 (6)0.0176 (7)0.0157 (5)0.0013 (5)0.0007 (4)0.0012 (5)
C4A0.0149 (6)0.0189 (8)0.0171 (5)0.0003 (5)0.0009 (4)0.0017 (5)
C5A0.0169 (6)0.0175 (8)0.0189 (5)0.0025 (6)0.0030 (5)0.0011 (5)
C6A0.0199 (6)0.0189 (8)0.0179 (5)0.0004 (6)0.0016 (5)0.0029 (5)
C7A0.0154 (6)0.0187 (8)0.0162 (5)0.0020 (6)0.0005 (4)0.0005 (5)
C8A0.0179 (6)0.0231 (8)0.0187 (5)0.0001 (6)0.0021 (5)0.0046 (5)
C9A0.0147 (6)0.0209 (8)0.0178 (5)0.0014 (6)0.0031 (4)0.0014 (5)
C10A0.0164 (6)0.0212 (8)0.0184 (5)0.0000 (6)0.0024 (4)0.0002 (5)
C11A0.0195 (6)0.0270 (9)0.0230 (6)0.0040 (6)0.0063 (5)0.0044 (6)
C12A0.0165 (6)0.0203 (8)0.0199 (6)0.0020 (6)0.0041 (5)0.0004 (5)
C13A0.0156 (6)0.0188 (8)0.0218 (6)0.0020 (6)0.0022 (5)0.0028 (5)
C14A0.0166 (6)0.0197 (8)0.0215 (6)0.0026 (6)0.0023 (5)0.0030 (5)
C15A0.0214 (7)0.0236 (9)0.0226 (6)0.0046 (6)0.0006 (5)0.0017 (6)
C16A0.0268 (7)0.0305 (10)0.0226 (6)0.0064 (7)0.0040 (5)0.0048 (6)
C17A0.0262 (7)0.0288 (10)0.0305 (7)0.0042 (7)0.0089 (6)0.0118 (7)
C18A0.0228 (7)0.0200 (9)0.0328 (7)0.0009 (6)0.0041 (6)0.0032 (6)
C19A0.0179 (6)0.0187 (8)0.0245 (6)0.0037 (6)0.0030 (5)0.0013 (6)
C20A0.0182 (6)0.0191 (8)0.0266 (6)0.0027 (6)0.0036 (5)0.0004 (6)
C21A0.0168 (6)0.0210 (8)0.0204 (6)0.0007 (6)0.0021 (5)0.0011 (5)
C22A0.0210 (7)0.0243 (9)0.0232 (6)0.0001 (6)0.0026 (5)0.0029 (6)
C23A0.0248 (7)0.0234 (9)0.0356 (8)0.0026 (7)0.0002 (6)0.0019 (7)
C24A0.0236 (7)0.0252 (9)0.0298 (7)0.0006 (7)0.0040 (6)0.0069 (6)
C25A0.0272 (7)0.0306 (10)0.0220 (6)0.0000 (7)0.0012 (5)0.0016 (6)
C26A0.0253 (7)0.0244 (9)0.0201 (6)0.0029 (7)0.0034 (5)0.0013 (6)
C27A0.0239 (7)0.0297 (9)0.0193 (6)0.0036 (7)0.0068 (5)0.0014 (6)
C28A0.0241 (7)0.0224 (9)0.0249 (6)0.0032 (6)0.0077 (5)0.0046 (6)
C29A0.0239 (7)0.0332 (11)0.0338 (8)0.0120 (7)0.0092 (6)0.0071 (7)
F1B0.0692 (8)0.0313 (7)0.0496 (6)0.0141 (6)0.0230 (6)0.0227 (5)
O1B0.0152 (4)0.0251 (6)0.0226 (4)0.0025 (4)0.0032 (3)0.0027 (4)
O2B0.0222 (5)0.0258 (6)0.0163 (4)0.0008 (5)0.0024 (3)0.0082 (4)
O3B0.0190 (5)0.0203 (6)0.0212 (4)0.0058 (4)0.0014 (3)0.0047 (4)
O4B0.0228 (5)0.0242 (7)0.0325 (5)0.0055 (5)0.0006 (4)0.0008 (5)
O5B0.0192 (5)0.0313 (7)0.0305 (5)0.0025 (5)0.0009 (4)0.0025 (5)
N1B0.0228 (6)0.0196 (7)0.0167 (5)0.0028 (5)0.0027 (4)0.0037 (5)
C1B0.0147 (6)0.0165 (7)0.0146 (5)0.0004 (5)0.0011 (4)0.0012 (5)
C2B0.0150 (6)0.0147 (7)0.0144 (5)0.0001 (5)0.0013 (4)0.0006 (5)
C3B0.0147 (6)0.0184 (8)0.0159 (5)0.0015 (5)0.0025 (4)0.0008 (5)
C4B0.0181 (6)0.0165 (7)0.0138 (5)0.0024 (5)0.0008 (4)0.0020 (5)
C5B0.0167 (6)0.0156 (7)0.0164 (5)0.0018 (5)0.0015 (4)0.0001 (5)
C6B0.0159 (6)0.0167 (7)0.0159 (5)0.0010 (5)0.0026 (4)0.0000 (5)
C7B0.0149 (6)0.0149 (7)0.0142 (5)0.0001 (5)0.0014 (4)0.0004 (5)
C8B0.0156 (6)0.0172 (7)0.0159 (5)0.0025 (5)0.0032 (4)0.0024 (5)
C9B0.0150 (6)0.0153 (7)0.0155 (5)0.0011 (5)0.0019 (4)0.0022 (5)
C10B0.0184 (6)0.0170 (8)0.0160 (5)0.0020 (6)0.0004 (4)0.0026 (5)
C11B0.0308 (8)0.0253 (9)0.0175 (6)0.0058 (7)0.0025 (5)0.0066 (6)
C12B0.0165 (6)0.0176 (8)0.0165 (5)0.0003 (6)0.0018 (4)0.0018 (5)
C13B0.0188 (6)0.0177 (8)0.0221 (6)0.0013 (6)0.0033 (5)0.0010 (5)
C14B0.0262 (7)0.0172 (8)0.0223 (6)0.0033 (6)0.0057 (5)0.0027 (6)
C15B0.0337 (8)0.0252 (9)0.0298 (7)0.0049 (7)0.0115 (6)0.0092 (7)
C16B0.0518 (11)0.0295 (10)0.0269 (7)0.0137 (9)0.0181 (7)0.0110 (7)
C17B0.0586 (12)0.0276 (10)0.0184 (6)0.0126 (9)0.0022 (7)0.0034 (6)
C18B0.0405 (9)0.0243 (9)0.0200 (6)0.0078 (7)0.0044 (6)0.0006 (6)
C19B0.0289 (7)0.0162 (8)0.0183 (6)0.0059 (6)0.0014 (5)0.0019 (5)
C20B0.0189 (6)0.0180 (8)0.0200 (6)0.0019 (6)0.0002 (5)0.0027 (5)
C21B0.0209 (6)0.0181 (8)0.0148 (5)0.0034 (6)0.0017 (4)0.0022 (5)
C22B0.0224 (7)0.0202 (8)0.0215 (6)0.0024 (6)0.0019 (5)0.0016 (6)
C23B0.0337 (8)0.0184 (9)0.0334 (7)0.0004 (7)0.0112 (6)0.0002 (6)
C24B0.0471 (10)0.0220 (9)0.0288 (7)0.0124 (8)0.0166 (7)0.0098 (7)
C25B0.0365 (9)0.0349 (11)0.0191 (6)0.0173 (8)0.0046 (6)0.0044 (6)
C26B0.0242 (7)0.0312 (10)0.0155 (5)0.0076 (7)0.0002 (5)0.0017 (6)
C27B0.0257 (7)0.0367 (11)0.0193 (6)0.0002 (7)0.0067 (5)0.0064 (6)
C28B0.0212 (7)0.0237 (9)0.0291 (7)0.0072 (6)0.0040 (5)0.0031 (6)
C29B0.0307 (8)0.0212 (9)0.0267 (7)0.0043 (7)0.0023 (6)0.0046 (6)
O60.0455 (8)0.0322 (8)0.0409 (7)0.0065 (6)0.0185 (6)0.0034 (6)
C300.0367 (9)0.0344 (11)0.0346 (8)0.0034 (8)0.0009 (7)0.0008 (8)
Geometric parameters (Å, º) top
F1A—C24A1.3597 (19)O2B—C27B1.4302 (18)
O1A—C1A1.2158 (18)O3B—C5B1.3534 (17)
O2A—C4A1.3624 (16)O3B—C28B1.4351 (18)
O2A—C27A1.4376 (18)O4B—C13B1.2093 (18)
O3A—C5A1.3575 (17)O5B—C20B1.2116 (18)
O3A—C28A1.4366 (17)N1B—C12B1.4446 (17)
O4A—C13A1.2170 (19)N1B—C29B1.452 (2)
O5A—C20A1.210 (2)N1B—C11B1.4719 (18)
N1A—C12A1.4455 (17)C1B—C2B1.4538 (19)
N1A—C29A1.453 (2)C1B—C9B1.5433 (18)
N1A—C11A1.471 (2)C2B—C7B1.3877 (18)
C1A—C2A1.4604 (19)C2B—C3B1.4064 (18)
C1A—C9A1.5432 (18)C3B—C4B1.376 (2)
C2A—C7A1.3848 (19)C3B—H3BA0.9500
C2A—C3A1.4034 (18)C4B—C5B1.4290 (19)
C3A—C4A1.377 (2)C5B—C6B1.3924 (18)
C3A—H3AA0.9500C6B—C7B1.396 (2)
C4A—C5A1.4326 (19)C6B—H6BA0.9500
C5A—C6A1.3888 (19)C7B—C8B1.5132 (18)
C6A—C7A1.391 (2)C8B—C9B1.5499 (19)
C6A—H6AA0.9500C8B—H8BA0.9900
C7A—C8A1.5138 (19)C8B—H8BB0.9900
C8A—C9A1.547 (2)C9B—C10B1.5570 (17)
C8A—H8AA0.9900C9B—C12B1.571 (2)
C8A—H8AB0.9900C10B—C21B1.515 (2)
C9A—C10A1.552 (2)C10B—C11B1.536 (2)
C9A—C12A1.575 (2)C10B—H10B1.0000
C10A—C21A1.514 (2)C11B—H11C0.9900
C10A—C11A1.536 (2)C11B—H11D0.9900
C10A—H10A1.0000C12B—C20B1.5446 (18)
C11A—H11A0.9900C12B—C13B1.554 (2)
C11A—H11B0.9900C13B—C14B1.4944 (19)
C12A—C20A1.542 (2)C14B—C19B1.383 (2)
C12A—C13A1.555 (2)C14B—C15B1.390 (2)
C13A—C14A1.4801 (19)C15B—C16B1.396 (2)
C14A—C19A1.397 (2)C15B—H15B0.9500
C14A—C15A1.4000 (19)C16B—C17B1.389 (3)
C15A—C16A1.386 (2)C16B—H16B0.9500
C15A—H15A0.9500C17B—C18B1.388 (2)
C16A—C17A1.394 (3)C17B—H17B0.9500
C16A—H16A0.9500C18B—C19B1.3959 (19)
C17A—C18A1.395 (2)C18B—H18B0.9500
C17A—H17A0.9500C19B—C20B1.4874 (19)
C18A—C19A1.393 (2)C21B—C22B1.393 (2)
C18A—H18A0.9500C21B—C26B1.404 (2)
C19A—C20A1.4853 (19)C22B—C23B1.393 (2)
C21A—C22A1.394 (2)C22B—H22B0.9500
C21A—C26A1.4004 (19)C23B—C24B1.379 (3)
C22A—C23A1.385 (2)C23B—H23B0.9500
C22A—H22A0.9500C24B—C25B1.375 (3)
C23A—C24A1.382 (2)C25B—C26B1.386 (2)
C23A—H23A0.9500C25B—H25B0.9500
C24A—C25A1.373 (3)C26B—H26B0.9500
C25A—C26A1.386 (2)C27B—H27D0.9800
C25A—H25A0.9500C27B—H27E0.9800
C26A—H26A0.9500C27B—H27F0.9800
C27A—H27A0.9800C28B—H28D0.9800
C27A—H27B0.9800C28B—H28E0.9800
C27A—H27C0.9800C28B—H28F0.9800
C28A—H28A0.9800C29B—H29D0.9800
C28A—H28B0.9800C29B—H29E0.9800
C28A—H28C0.9800C29B—H29F0.9800
C29A—H29A0.9800O6—C301.412 (2)
C29A—H29B0.9800O6—H1O60.97 (3)
C29A—H29C0.9800C30—H30A0.9800
F1B—C24B1.361 (2)C30—H30B0.9800
O1B—C1B1.2199 (16)C30—H30C0.9800
O2B—C4B1.3666 (15)
C4A—O2A—C27A115.02 (11)C29B—N1B—C11B115.32 (12)
C5A—O3A—C28A116.30 (11)O1B—C1B—C2B128.19 (12)
C12A—N1A—C29A116.75 (12)O1B—C1B—C9B124.33 (13)
C12A—N1A—C11A108.41 (12)C2B—C1B—C9B107.44 (11)
C29A—N1A—C11A114.61 (13)C7B—C2B—C3B121.97 (12)
O1A—C1A—C2A128.48 (12)C7B—C2B—C1B110.27 (11)
O1A—C1A—C9A124.55 (13)C3B—C2B—C1B127.75 (12)
C2A—C1A—C9A106.89 (12)C4B—C3B—C2B117.99 (12)
C7A—C2A—C3A122.12 (13)C4B—C3B—H3BA121.0
C7A—C2A—C1A110.24 (12)C2B—C3B—H3BA121.0
C3A—C2A—C1A127.63 (12)O2B—C4B—C3B124.76 (12)
C4A—C3A—C2A118.32 (12)O2B—C4B—C5B114.92 (12)
C4A—C3A—H3AA120.8C3B—C4B—C5B120.32 (12)
C2A—C3A—H3AA120.8O3B—C5B—C6B124.81 (12)
O2A—C4A—C3A125.29 (12)O3B—C5B—C4B114.41 (11)
O2A—C4A—C5A114.93 (12)C6B—C5B—C4B120.77 (13)
C3A—C4A—C5A119.78 (12)C5B—C6B—C7B118.38 (12)
O3A—C5A—C6A124.46 (13)C5B—C6B—H6BA120.8
O3A—C5A—C4A114.67 (12)C7B—C6B—H6BA120.8
C6A—C5A—C4A120.87 (13)C2B—C7B—C6B120.30 (12)
C5A—C6A—C7A118.75 (13)C2B—C7B—C8B111.54 (12)
C5A—C6A—H6AA120.6C6B—C7B—C8B128.16 (12)
C7A—C6A—H6AA120.6C7B—C8B—C9B104.23 (10)
C2A—C7A—C6A120.11 (12)C7B—C8B—H8BA110.9
C2A—C7A—C8A111.69 (12)C9B—C8B—H8BA110.9
C6A—C7A—C8A128.20 (12)C7B—C8B—H8BB110.9
C7A—C8A—C9A103.75 (10)C9B—C8B—H8BB110.9
C7A—C8A—H8AA111.0H8BA—C8B—H8BB108.9
C9A—C8A—H8AA111.0C1B—C9B—C8B104.67 (11)
C7A—C8A—H8AB111.0C1B—C9B—C10B113.81 (11)
C9A—C8A—H8AB111.0C8B—C9B—C10B116.14 (11)
H8AA—C8A—H8AB109.0C1B—C9B—C12B110.37 (11)
C1A—C9A—C8A104.88 (11)C8B—C9B—C12B112.50 (11)
C1A—C9A—C10A115.06 (13)C10B—C9B—C12B99.51 (11)
C8A—C9A—C10A116.55 (11)C21B—C10B—C11B118.27 (11)
C1A—C9A—C12A110.14 (10)C21B—C10B—C9B113.91 (12)
C8A—C9A—C12A110.85 (13)C11B—C10B—C9B104.20 (11)
C10A—C9A—C12A99.37 (11)C21B—C10B—H10B106.6
C21A—C10A—C11A117.53 (11)C11B—C10B—H10B106.6
C21A—C10A—C9A115.12 (11)C9B—C10B—H10B106.6
C11A—C10A—C9A103.80 (13)N1B—C11B—C10B105.86 (11)
C21A—C10A—H10A106.5N1B—C11B—H11C110.6
C11A—C10A—H10A106.5C10B—C11B—H11C110.6
C9A—C10A—H10A106.5N1B—C11B—H11D110.6
N1A—C11A—C10A105.57 (11)C10B—C11B—H11D110.6
N1A—C11A—H11A110.6H11C—C11B—H11D108.7
C10A—C11A—H11A110.6N1B—C12B—C20B114.99 (11)
N1A—C11A—H11B110.6N1B—C12B—C13B116.42 (12)
C10A—C11A—H11B110.6C20B—C12B—C13B101.69 (11)
H11A—C11A—H11B108.8N1B—C12B—C9B102.18 (10)
N1A—C12A—C20A114.62 (13)C20B—C12B—C9B111.04 (12)
N1A—C12A—C13A117.24 (12)C13B—C12B—C9B110.80 (11)
C20A—C12A—C13A101.88 (11)O4B—C13B—C14B127.71 (14)
N1A—C12A—C9A100.64 (10)O4B—C13B—C12B125.50 (12)
C20A—C12A—C9A112.52 (11)C14B—C13B—C12B106.74 (12)
C13A—C12A—C9A110.33 (12)C19B—C14B—C15B121.37 (14)
O4A—C13A—C14A126.67 (13)C19B—C14B—C13B109.69 (12)
O4A—C13A—C12A125.80 (12)C15B—C14B—C13B128.90 (15)
C14A—C13A—C12A107.41 (12)C14B—C15B—C16B117.09 (17)
C19A—C14A—C15A121.28 (14)C14B—C15B—H15B121.5
C19A—C14A—C13A109.84 (12)C16B—C15B—H15B121.5
C15A—C14A—C13A128.85 (15)C17B—C16B—C15B121.47 (15)
C16A—C15A—C14A117.07 (15)C17B—C16B—H16B119.3
C16A—C15A—H15A121.5C15B—C16B—H16B119.3
C14A—C15A—H15A121.5C18B—C17B—C16B121.29 (15)
C15A—C16A—C17A121.62 (14)C18B—C17B—H17B119.4
C15A—C16A—H16A119.2C16B—C17B—H17B119.4
C17A—C16A—H16A119.2C17B—C18B—C19B117.14 (16)
C16A—C17A—C18A121.63 (15)C17B—C18B—H18B121.4
C16A—C17A—H17A119.2C19B—C18B—H18B121.4
C18A—C17A—H17A119.2C14B—C19B—C18B121.59 (14)
C19A—C18A—C17A116.85 (16)C14B—C19B—C20B110.25 (12)
C19A—C18A—H18A121.6C18B—C19B—C20B128.15 (15)
C17A—C18A—H18A121.6O5B—C20B—C19B126.90 (13)
C18A—C19A—C14A121.54 (13)O5B—C20B—C12B126.49 (12)
C18A—C19A—C20A128.48 (15)C19B—C20B—C12B106.60 (11)
C14A—C19A—C20A109.87 (13)C22B—C21B—C26B118.36 (15)
O5A—C20A—C19A126.67 (15)C22B—C21B—C10B118.58 (12)
O5A—C20A—C12A125.97 (13)C26B—C21B—C10B122.96 (14)
C19A—C20A—C12A107.30 (13)C23B—C22B—C21B121.25 (15)
C22A—C21A—C26A117.97 (14)C23B—C22B—H22B119.4
C22A—C21A—C10A118.39 (12)C21B—C22B—H22B119.4
C26A—C21A—C10A123.64 (14)C24B—C23B—C22B118.00 (17)
C23A—C22A—C21A121.63 (14)C24B—C23B—H23B121.0
C23A—C22A—H22A119.2C22B—C23B—H23B121.0
C21A—C22A—H22A119.2F1B—C24B—C25B118.34 (17)
C24A—C23A—C22A118.22 (16)F1B—C24B—C23B118.70 (18)
C24A—C23A—H23A120.9C25B—C24B—C23B122.96 (16)
C22A—C23A—H23A120.9C24B—C25B—C26B118.30 (15)
F1A—C24A—C25A119.12 (14)C24B—C25B—H25B120.8
F1A—C24A—C23A118.55 (16)C26B—C25B—H25B120.8
C25A—C24A—C23A122.33 (15)C25B—C26B—C21B121.11 (16)
C24A—C25A—C26A118.66 (14)C25B—C26B—H26B119.4
C24A—C25A—H25A120.7C21B—C26B—H26B119.4
C26A—C25A—H25A120.7O2B—C27B—H27D109.5
C25A—C26A—C21A121.16 (15)O2B—C27B—H27E109.5
C25A—C26A—H26A119.4H27D—C27B—H27E109.5
C21A—C26A—H26A119.4O2B—C27B—H27F109.5
O2A—C27A—H27A109.5H27D—C27B—H27F109.5
O2A—C27A—H27B109.5H27E—C27B—H27F109.5
H27A—C27A—H27B109.5O3B—C28B—H28D109.5
O2A—C27A—H27C109.5O3B—C28B—H28E109.5
H27A—C27A—H27C109.5H28D—C28B—H28E109.5
H27B—C27A—H27C109.5O3B—C28B—H28F109.5
O3A—C28A—H28A109.5H28D—C28B—H28F109.5
O3A—C28A—H28B109.5H28E—C28B—H28F109.5
H28A—C28A—H28B109.5N1B—C29B—H29D109.5
O3A—C28A—H28C109.5N1B—C29B—H29E109.5
H28A—C28A—H28C109.5H29D—C29B—H29E109.5
H28B—C28A—H28C109.5N1B—C29B—H29F109.5
N1A—C29A—H29A109.5H29D—C29B—H29F109.5
N1A—C29A—H29B109.5H29E—C29B—H29F109.5
H29A—C29A—H29B109.5C30—O6—H1O6111.3 (18)
N1A—C29A—H29C109.5O6—C30—H30A109.5
H29A—C29A—H29C109.5O6—C30—H30B109.5
H29B—C29A—H29C109.5H30A—C30—H30B109.5
C4B—O2B—C27B115.48 (12)O6—C30—H30C109.5
C5B—O3B—C28B117.48 (11)H30A—C30—H30C109.5
C12B—N1B—C29B116.36 (12)H30B—C30—H30C109.5
C12B—N1B—C11B108.74 (11)
O1A—C1A—C2A—C7A172.47 (15)O1B—C1B—C2B—C7B171.09 (14)
C9A—C1A—C2A—C7A10.63 (16)C9B—C1B—C2B—C7B10.90 (15)
O1A—C1A—C2A—C3A8.6 (3)O1B—C1B—C2B—C3B9.2 (2)
C9A—C1A—C2A—C3A168.33 (14)C9B—C1B—C2B—C3B168.79 (14)
C7A—C2A—C3A—C4A0.3 (2)C7B—C2B—C3B—C4B1.0 (2)
C1A—C2A—C3A—C4A179.15 (14)C1B—C2B—C3B—C4B179.30 (14)
C27A—O2A—C4A—C3A3.5 (2)C27B—O2B—C4B—C3B11.1 (2)
C27A—O2A—C4A—C5A177.05 (13)C27B—O2B—C4B—C5B169.22 (13)
C2A—C3A—C4A—O2A178.90 (13)C2B—C3B—C4B—O2B176.79 (13)
C2A—C3A—C4A—C5A1.7 (2)C2B—C3B—C4B—C5B3.6 (2)
C28A—O3A—C5A—C6A16.5 (2)C28B—O3B—C5B—C6B10.0 (2)
C28A—O3A—C5A—C4A163.83 (13)C28B—O3B—C5B—C4B171.30 (13)
O2A—C4A—C5A—O3A1.07 (19)O2B—C4B—C5B—O3B3.72 (18)
C3A—C4A—C5A—O3A178.39 (13)C3B—C4B—C5B—O3B175.95 (13)
O2A—C4A—C5A—C6A178.61 (13)O2B—C4B—C5B—C6B175.04 (13)
C3A—C4A—C5A—C6A1.9 (2)C3B—C4B—C5B—C6B5.3 (2)
O3A—C5A—C6A—C7A179.75 (14)O3B—C5B—C6B—C7B179.17 (13)
C4A—C5A—C6A—C7A0.1 (2)C4B—C5B—C6B—C7B2.2 (2)
C3A—C2A—C7A—C6A2.1 (2)C3B—C2B—C7B—C6B4.1 (2)
C1A—C2A—C7A—C6A178.83 (13)C1B—C2B—C7B—C6B176.18 (13)
C3A—C2A—C7A—C8A178.17 (13)C3B—C2B—C7B—C8B176.41 (13)
C1A—C2A—C7A—C8A0.85 (17)C1B—C2B—C7B—C8B3.30 (16)
C5A—C6A—C7A—C2A1.9 (2)C5B—C6B—C7B—C2B2.4 (2)
C5A—C6A—C7A—C8A178.49 (14)C5B—C6B—C7B—C8B178.24 (14)
C2A—C7A—C8A—C9A9.12 (17)C2B—C7B—C8B—C9B5.56 (15)
C6A—C7A—C8A—C9A171.23 (15)C6B—C7B—C8B—C9B175.01 (14)
O1A—C1A—C9A—C8A167.21 (15)O1B—C1B—C9B—C8B168.11 (13)
C2A—C1A—C9A—C8A15.74 (15)C2B—C1B—C9B—C8B13.78 (14)
O1A—C1A—C9A—C10A37.81 (19)O1B—C1B—C9B—C10B40.27 (19)
C2A—C1A—C9A—C10A145.14 (12)C2B—C1B—C9B—C10B141.62 (12)
O1A—C1A—C9A—C12A73.47 (19)O1B—C1B—C9B—C12B70.62 (16)
C2A—C1A—C9A—C12A103.58 (13)C2B—C1B—C9B—C12B107.49 (12)
C7A—C8A—C9A—C1A14.71 (15)C7B—C8B—C9B—C1B11.48 (14)
C7A—C8A—C9A—C10A143.22 (13)C7B—C8B—C9B—C10B137.88 (12)
C7A—C8A—C9A—C12A104.13 (13)C7B—C8B—C9B—C12B108.38 (12)
C1A—C9A—C10A—C21A77.09 (15)C1B—C9B—C10B—C21B78.01 (15)
C8A—C9A—C10A—C21A46.31 (18)C8B—C9B—C10B—C21B43.66 (17)
C12A—C9A—C10A—C21A165.37 (12)C12B—C9B—C10B—C21B164.63 (11)
C1A—C9A—C10A—C11A153.05 (11)C1B—C9B—C10B—C11B151.70 (13)
C8A—C9A—C10A—C11A83.55 (14)C8B—C9B—C10B—C11B86.63 (15)
C12A—C9A—C10A—C11A35.51 (13)C12B—C9B—C10B—C11B34.33 (13)
C12A—N1A—C11A—C10A17.98 (15)C12B—N1B—C11B—C10B15.16 (17)
C29A—N1A—C11A—C10A150.38 (13)C29B—N1B—C11B—C10B147.94 (13)
C21A—C10A—C11A—N1A141.21 (13)C21B—C10B—C11B—N1B141.35 (13)
C9A—C10A—C11A—N1A12.82 (14)C9B—C10B—C11B—N1B13.70 (16)
C29A—N1A—C12A—C20A67.19 (18)C29B—N1B—C12B—C20B70.02 (17)
C11A—N1A—C12A—C20A161.56 (12)C11B—N1B—C12B—C20B157.75 (13)
C29A—N1A—C12A—C13A52.2 (2)C29B—N1B—C12B—C13B48.74 (17)
C11A—N1A—C12A—C13A79.06 (15)C11B—N1B—C12B—C13B83.49 (16)
C29A—N1A—C12A—C9A171.83 (14)C29B—N1B—C12B—C9B169.60 (12)
C11A—N1A—C12A—C9A40.58 (14)C11B—N1B—C12B—C9B37.37 (15)
C1A—C9A—C12A—N1A167.34 (12)C1B—C9B—C12B—N1B163.49 (10)
C8A—C9A—C12A—N1A77.04 (14)C8B—C9B—C12B—N1B80.01 (12)
C10A—C9A—C12A—N1A46.16 (13)C10B—C9B—C12B—N1B43.56 (12)
C1A—C9A—C12A—C20A70.19 (15)C1B—C9B—C12B—C20B73.41 (13)
C8A—C9A—C12A—C20A45.42 (14)C8B—C9B—C12B—C20B43.09 (14)
C10A—C9A—C12A—C20A168.62 (11)C10B—C9B—C12B—C20B166.66 (10)
C1A—C9A—C12A—C13A42.84 (16)C1B—C9B—C12B—C13B38.82 (14)
C8A—C9A—C12A—C13A158.46 (11)C8B—C9B—C12B—C13B155.32 (10)
C10A—C9A—C12A—C13A78.34 (13)C10B—C9B—C12B—C13B81.11 (12)
N1A—C12A—C13A—O4A32.5 (2)N1B—C12B—C13B—O4B31.6 (2)
C20A—C12A—C13A—O4A158.50 (15)C20B—C12B—C13B—O4B157.37 (16)
C9A—C12A—C13A—O4A81.81 (18)C9B—C12B—C13B—O4B84.55 (18)
N1A—C12A—C13A—C14A143.58 (13)N1B—C12B—C13B—C14B145.98 (13)
C20A—C12A—C13A—C14A17.63 (14)C20B—C12B—C13B—C14B20.21 (15)
C9A—C12A—C13A—C14A102.07 (14)C9B—C12B—C13B—C14B97.87 (13)
O4A—C13A—C14A—C19A165.60 (15)O4B—C13B—C14B—C19B165.96 (17)
C12A—C13A—C14A—C19A10.48 (16)C12B—C13B—C14B—C19B11.55 (18)
O4A—C13A—C14A—C15A12.3 (3)O4B—C13B—C14B—C15B16.3 (3)
C12A—C13A—C14A—C15A171.57 (15)C12B—C13B—C14B—C15B166.19 (17)
C19A—C14A—C15A—C16A0.5 (2)C19B—C14B—C15B—C16B1.6 (3)
C13A—C14A—C15A—C16A177.23 (15)C13B—C14B—C15B—C16B175.89 (17)
C14A—C15A—C16A—C17A0.7 (2)C14B—C15B—C16B—C17B1.1 (3)
C15A—C16A—C17A—C18A0.2 (3)C15B—C16B—C17B—C18B0.8 (3)
C16A—C17A—C18A—C19A0.6 (2)C16B—C17B—C18B—C19B2.2 (3)
C17A—C18A—C19A—C14A0.8 (2)C15B—C14B—C19B—C18B0.2 (3)
C17A—C18A—C19A—C20A174.99 (15)C13B—C14B—C19B—C18B177.76 (15)
C15A—C14A—C19A—C18A0.2 (2)C15B—C14B—C19B—C20B179.10 (15)
C13A—C14A—C19A—C18A178.36 (14)C13B—C14B—C19B—C20B2.96 (19)
C15A—C14A—C19A—C20A176.23 (13)C17B—C18B—C19B—C14B1.8 (3)
C13A—C14A—C19A—C20A1.90 (17)C17B—C18B—C19B—C20B179.11 (17)
C18A—C19A—C20A—O5A12.4 (3)C14B—C19B—C20B—O5B162.86 (17)
C14A—C19A—C20A—O5A163.70 (15)C18B—C19B—C20B—O5B16.4 (3)
C18A—C19A—C20A—C12A170.24 (15)C14B—C19B—C20B—C12B16.38 (18)
C14A—C19A—C20A—C12A13.61 (16)C18B—C19B—C20B—C12B164.40 (16)
N1A—C12A—C20A—O5A31.0 (2)N1B—C12B—C20B—O5B30.7 (2)
C13A—C12A—C20A—O5A158.67 (15)C13B—C12B—C20B—O5B157.38 (17)
C9A—C12A—C20A—O5A83.19 (18)C9B—C12B—C20B—O5B84.71 (19)
N1A—C12A—C20A—C19A146.33 (12)N1B—C12B—C20B—C19B148.57 (13)
C13A—C12A—C20A—C19A18.67 (14)C13B—C12B—C20B—C19B21.86 (16)
C9A—C12A—C20A—C19A99.47 (13)C9B—C12B—C20B—C19B96.05 (14)
C11A—C10A—C21A—C22A152.37 (15)C11B—C10B—C21B—C22B149.87 (13)
C9A—C10A—C21A—C22A84.84 (17)C9B—C10B—C21B—C22B87.23 (15)
C11A—C10A—C21A—C26A27.8 (2)C11B—C10B—C21B—C26B33.80 (19)
C9A—C10A—C21A—C26A94.95 (17)C9B—C10B—C21B—C26B89.10 (16)
C26A—C21A—C22A—C23A1.1 (2)C26B—C21B—C22B—C23B1.6 (2)
C10A—C21A—C22A—C23A179.15 (14)C10B—C21B—C22B—C23B178.14 (13)
C21A—C22A—C23A—C24A0.5 (2)C21B—C22B—C23B—C24B0.9 (2)
C22A—C23A—C24A—F1A177.43 (15)C22B—C23B—C24B—F1B179.86 (14)
C22A—C23A—C24A—C25A1.9 (3)C22B—C23B—C24B—C25B0.5 (2)
F1A—C24A—C25A—C26A177.74 (15)F1B—C24B—C25B—C26B179.24 (14)
C23A—C24A—C25A—C26A1.6 (3)C23B—C24B—C25B—C26B1.1 (2)
C24A—C25A—C26A—C21A0.1 (2)C24B—C25B—C26B—C21B0.3 (2)
C22A—C21A—C26A—C25A1.4 (2)C22B—C21B—C26B—C25B1.0 (2)
C10A—C21A—C26A—C25A178.84 (15)C10B—C21B—C26B—C25B177.34 (13)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
O6—H1O6···O4A0.97 (3)1.99 (3)2.9346 (18)164 (3)
C8A—H8AA···O5A0.992.433.088 (2)124
C8B—H8BA···O5B0.992.383.0960 (19)128
C26A—H26A···O5Ai0.952.543.2430 (18)131
C27A—H27A···N1Bii0.982.423.337 (2)155
C28A—H28A···O2Biii0.982.503.3478 (19)145
C28B—H28F···O6iv0.982.463.360 (2)153
C30—H30B···F1Av0.982.533.307 (2)136
Symmetry codes: (i) x+1, y+2, z+2; (ii) x+2, y+1/2, z+3/2; (iii) x+2, y+2, z+2; (iv) x+1, y, z; (v) x+1, y+1, z+2.

Experimental details

Crystal data
Chemical formulaC29H24FNO5·0.5CH4O
Mr501.52
Crystal system, space groupMonoclinic, P21/c
Temperature (K)100
a, b, c (Å)14.6385 (6), 12.5099 (6), 26.2017 (10)
β (°) 92.645 (1)
V3)4793.1 (4)
Z8
Radiation typeMo Kα
µ (mm1)0.10
Crystal size (mm)0.44 × 0.21 × 0.15
Data collection
DiffractometerBruker APEX DUO CCD area-detector
Absorption correctionMulti-scan
(SADABS; Bruker, 2009)
Tmin, Tmax0.957, 0.985
No. of measured, independent and
observed [I > 2σ(I)] reflections
53390, 14094, 10283
Rint0.046
(sin θ/λ)max1)0.709
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.049, 0.147, 1.04
No. of reflections14094
No. of parameters678
H-atom treatmentH atoms treated by a mixture of independent and constrained refinement
Δρmax, Δρmin (e Å3)0.40, 0.27

Computer programs: APEX2 (Bruker, 2009), SAINT (Bruker, 2009), SHELXTL (Sheldrick, 2008) and PLATON (Spek, 2009).

Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
O6—H1O6···O4A0.97 (3)1.99 (3)2.9346 (18)164 (3)
C8A—H8AA···O5A0.992.433.088 (2)124
C8B—H8BA···O5B0.992.383.0960 (19)128
C26A—H26A···O5Ai0.952.543.2430 (18)131
C27A—H27A···N1Bii0.982.423.337 (2)155
C28A—H28A···O2Biii0.982.503.3478 (19)145
C28B—H28F···O6iv0.982.463.360 (2)153
C30—H30B···F1Av0.982.533.307 (2)136
Symmetry codes: (i) x+1, y+2, z+2; (ii) x+2, y+1/2, z+3/2; (iii) x+2, y+2, z+2; (iv) x+1, y, z; (v) x+1, y+1, z+2.
 

Footnotes

Thomson Reuters ResearcherID: A-5599-2009.

Acknowledgements

The authors wish to express their gratitude and appreciation to the Pharmacogenetics and Novel Therapeutics Research Cluster, Institute for Research in Mol­ecular Medicine, Universiti Sains Malaysia (USM), Penang, for support of this work. This work was funded through Research Grant No. RUC (1001/PSK/8620012) and HiCoE Research Grant No (311.CIPPM.4401005). IAR also thanks USM for the Short Term Grant, No. 304/PFIZIK/6312078.

References

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