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The title acridone alkaloid compound [systematic name: 6,11-dihydr­oxy-3,3,12-trimethyl-5-(3-methyl­but-2-en­yl)-3,12-dihydro-7H-pyrano[2,3-c]acridin-7-one], C24H25NO4, was isolated from Atalantia monophylla Corrêa, a mangrove plant. The mol­ecule contains four fused rings. The pyridine ring is in an envelope conformation and the chromene ring adopts a screw-boat conformation. An intra­molecular O—H...O hydrogen bond generates an S(6) ring motif. In the crystal structure, the mol­ecules are linked into chains along the b axis by O—H...O hydrogen bonds. These chains are inter­connected into mol­ecular sheets parallel to the bc plane by weak C—H...O inter­actions. The crystal structure is further stabilized by C—H...π inter­actions.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536807038238/ci2432sup1.cif
Contains datablocks global, I

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536807038238/ci2432Isup2.hkl
Contains datablock I

CCDC reference: 662408

Key indicators

  • Single-crystal X-ray study
  • T = 100 K
  • Mean [sigma](C-C) = 0.002 Å
  • R factor = 0.045
  • wR factor = 0.129
  • Data-to-parameter ratio = 20.5

checkCIF/PLATON results

No syntax errors found



Alert level C PLAT066_ALERT_1_C Predicted and Reported Transmissions Identical . ? PLAT154_ALERT_1_C The su's on the Cell Angles are Equal (x 10000) 100 Deg. PLAT180_ALERT_3_C Check Cell Rounding: # of Values Ending with 0 = 5 PLAT222_ALERT_3_C Large Non-Solvent H Ueq(max)/Ueq(min) ... 3.19 Ratio PLAT380_ALERT_4_C Check Incorrectly? Oriented X(sp2)-Methyl Moiety C24 PLAT720_ALERT_4_C Number of Unusual/Non-Standard Label(s) ........ 2
0 ALERT level A = In general: serious problem 0 ALERT level B = Potentially serious problem 6 ALERT level C = Check and explain 0 ALERT level G = General alerts; check 2 ALERT type 1 CIF construction/syntax error, inconsistent or missing data 0 ALERT type 2 Indicator that the structure model may be wrong or deficient 2 ALERT type 3 Indicator that the structure quality may be low 2 ALERT type 4 Improvement, methodology, query or suggestion 0 ALERT type 5 Informative message, check

Comment top

Atalantia monophylla Corrêa is a mangrove plant, distributed in South-East Asia and known locally in Thai as Manao Phi. This plant has been used in folk medicine for several purposes such as the treatment of dysentery, chronic rheumatism and paralysis in India (Basa, 1975). Acridone alkaloids had been isolated from the petroleum ether extract of the root bark of this plant (Basu & Basa, 1972). In our continuing interest on the chemical constituents of Thai mangrove plants, we have examined the roots of A. monophylla collected from Trang Province in the southern part of Thailand. The title compound was isolated from the methylene chloride extract. It has shown several biological activities such as inhibition of EBV-EA induction (Itoigawa et al., 2003), antiviral (Kawaii et al., 1999a) and antiproliferative properties (Kawaii et al., 1999b).

The title molecule is chiral, but crystallized in the centrosymmetric space group P1. This indicates that the crude extract from which the compound was obtained is a racemic mixture and that the compound is a non-enzymatic product (Chantrapromma, Boonnak & Fun, 2005; Chantrapromma, Boonnak, Fun, Anjum et al., 2005; Fun et al., 2006; Kosela et al., 1999; Pancharoen et al., 1984).

The title molecule (Fig. 1) has a four-fused rings (A, B, C and D). The pyridine ring (B) is in an envelope conformation, with puckering parameters Q = 0.157 (1) Å, θ = 102.3 (4)° and φ = 170.5 (5)° (Cremer & Pople, 1975), atom N1 having the maximum deviation of 0.102 (1) Å. The chromene ring (D) adopts a screw-boat conformation, with the C14 and O4 atoms deviating from the ring mean plane by 0.276 (11) and -0.238 (1) Å, respectively. The prenyl group (C20–C24) is in a (-)-anticlinal conformation (Fig. 1), as evidenced by the torsion angle C2—C1—C20—C21 of -104.52 (13)°. The dihedral angle between the mean plane of the prenyl unit and the benzene ring C is 86.30 (7)°. The two methyl groups are axially and equatorially attached to the ring D at atom C14. The two hydroxyl groups are coplanar with the attached rings.

The bond lengths and angles in the title compound are within normal ranges (Allen et al., 1987).

Intramolecular O1—H1O1···O2 hydrogen bond generates an S(6) ring motif (Bernstein et al., 1995). The molecules are linked into a chain along the b axis by O3—H1O3···O1 hydrogen bonds (Fig. 2 and Table 1). These chains are interconnected into molecular sheets by weak C6—H6A···O2 hydrogen bonds (Table 1). In addition, the molecular packing is stabilized by C—H···π interactions involving the ring A (centroid Cg1).

Related literature top

For the biological activities of acridone alkaloids, see: Basa (1975); Basu & Basa (1972); Itoigawa et al. (2003); Kawaii et al. (1999a, 1999b). For hydrogen-bond motifs, see: Bernstein et al. (1995). For bond-length data, see: Allen et al. (1987). For ring conformations, see: Cremer & Pople (1975). For related structures of non-enzymatic products, see: Chantrapromma, Boonnak & Fun (2005); Chantrapromma, Boonnak, Fun et al. (2005); Fun et al. (2006); Kosela et al. (1999); Pancharoen et al. (1984).

Experimental top

Air-dried roots of A. monophylla (6.0 kg) were ground and extracted with methylene chloride (2 × 20 l) for 7 d at room temperature. The yellow viscous residue (52.5 g) obtained after evaporation of the solvent was subjected to quick column chromatography over silica gel using solvents of increasing polarity from n-hexane through EtOAc. The eluents were separated into 18 fractions (F1—F18) on the basis of TLC analysis. Fraction F6 (1.2 g) was further separated by quick column chromatography (QCC) with a gradient of acetone–hexane to afford eight subfractions (6 A-6H). Fraction 6 F was further purified by column chromatography (CC) eluting with 20% acetone-hexane to give two subfractions (6 F A and 6FB). Fraction 6 F A was recrystallized from acetone to yield brown single crystals of the title compound after several days (m.p. 468–469 K).

Refinement top

Hydroxyl H atoms were located in a difference map and isotropically refined. The remaining H atoms were positioned geometrically and allowed to ride on their parent atoms, with C—H distances in the range 0.93–0.97 Å. The Uiso values were constrained to be 1.5Ueq of the carrier atom for methyl H atoms and 1.2Ueq for the remaining H atoms. A rotating group model was used for the methyl groups.

Structure description top

Atalantia monophylla Corrêa is a mangrove plant, distributed in South-East Asia and known locally in Thai as Manao Phi. This plant has been used in folk medicine for several purposes such as the treatment of dysentery, chronic rheumatism and paralysis in India (Basa, 1975). Acridone alkaloids had been isolated from the petroleum ether extract of the root bark of this plant (Basu & Basa, 1972). In our continuing interest on the chemical constituents of Thai mangrove plants, we have examined the roots of A. monophylla collected from Trang Province in the southern part of Thailand. The title compound was isolated from the methylene chloride extract. It has shown several biological activities such as inhibition of EBV-EA induction (Itoigawa et al., 2003), antiviral (Kawaii et al., 1999a) and antiproliferative properties (Kawaii et al., 1999b).

The title molecule is chiral, but crystallized in the centrosymmetric space group P1. This indicates that the crude extract from which the compound was obtained is a racemic mixture and that the compound is a non-enzymatic product (Chantrapromma, Boonnak & Fun, 2005; Chantrapromma, Boonnak, Fun, Anjum et al., 2005; Fun et al., 2006; Kosela et al., 1999; Pancharoen et al., 1984).

The title molecule (Fig. 1) has a four-fused rings (A, B, C and D). The pyridine ring (B) is in an envelope conformation, with puckering parameters Q = 0.157 (1) Å, θ = 102.3 (4)° and φ = 170.5 (5)° (Cremer & Pople, 1975), atom N1 having the maximum deviation of 0.102 (1) Å. The chromene ring (D) adopts a screw-boat conformation, with the C14 and O4 atoms deviating from the ring mean plane by 0.276 (11) and -0.238 (1) Å, respectively. The prenyl group (C20–C24) is in a (-)-anticlinal conformation (Fig. 1), as evidenced by the torsion angle C2—C1—C20—C21 of -104.52 (13)°. The dihedral angle between the mean plane of the prenyl unit and the benzene ring C is 86.30 (7)°. The two methyl groups are axially and equatorially attached to the ring D at atom C14. The two hydroxyl groups are coplanar with the attached rings.

The bond lengths and angles in the title compound are within normal ranges (Allen et al., 1987).

Intramolecular O1—H1O1···O2 hydrogen bond generates an S(6) ring motif (Bernstein et al., 1995). The molecules are linked into a chain along the b axis by O3—H1O3···O1 hydrogen bonds (Fig. 2 and Table 1). These chains are interconnected into molecular sheets by weak C6—H6A···O2 hydrogen bonds (Table 1). In addition, the molecular packing is stabilized by C—H···π interactions involving the ring A (centroid Cg1).

For the biological activities of acridone alkaloids, see: Basa (1975); Basu & Basa (1972); Itoigawa et al. (2003); Kawaii et al. (1999a, 1999b). For hydrogen-bond motifs, see: Bernstein et al. (1995). For bond-length data, see: Allen et al. (1987). For ring conformations, see: Cremer & Pople (1975). For related structures of non-enzymatic products, see: Chantrapromma, Boonnak & Fun (2005); Chantrapromma, Boonnak, Fun et al. (2005); Fun et al. (2006); Kosela et al. (1999); Pancharoen et al. (1984).

Computing details top

Data collection: APEX2 (Bruker, 2005); cell refinement: APEX2; data reduction: SAINT (Bruker, 2005); program(s) used to solve structure: SHELXTL (Sheldrick, 1998); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL and PLATON (Spek, 2003).

Figures top
[Figure 1] Fig. 1. The molecular structure of the title compound, showing 50% probability displacement ellipsoids and the atomic numbering scheme. The hydrogen bond is shown as a dashed line.
[Figure 2] Fig. 2. The crystal packing of the title compound, viewed along the a axis. Hydrogen bonds are shown as dashed lines.
6,11-dihydroxy-3,3,12-trimethyl-5-(3-methylbut-2-enyl)-3,12-dihydro- 7H-pyrano[2,3-c]acridin-7-one top
Crystal data top
C24H25NO4Z = 2
Mr = 391.45F(000) = 416
Triclinic, P1Dx = 1.343 Mg m3
Hall symbol: -P 1Melting point = 468–469 K
a = 9.1387 (1) ÅMo Kα radiation, λ = 0.71073 Å
b = 9.7188 (1) ÅCell parameters from 5637 reflections
c = 11.7006 (2) Åθ = 2.1–30.0°
α = 90.796 (1)°µ = 0.09 mm1
β = 108.274 (1)°T = 100 K
γ = 100.432 (1)°Block, brown
V = 967.71 (2) Å30.20 × 0.17 × 0.13 mm
Data collection top
Bruker SMART APEXII CCD area-detector
diffractometer
5637 independent reflections
Radiation source: fine-focus sealed tube4346 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.039
Detector resolution: 8.33 pixels mm-1θmax = 30.0°, θmin = 2.1°
ω scansh = 1212
Absorption correction: multi-scan
(SADABS; Bruker, 2005)
k = 1313
Tmin = 0.982, Tmax = 0.989l = 1616
27568 measured reflections
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)] = 0.045Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.129H atoms treated by a mixture of independent and constrained refinement
S = 1.06 w = 1/[σ2(Fo2) + (0.063P)2 + 0.2437P]
where P = (Fo2 + 2Fc2)/3
5637 reflections(Δ/σ)max = 0.001
275 parametersΔρmax = 0.47 e Å3
0 restraintsΔρmin = 0.29 e Å3
Crystal data top
C24H25NO4γ = 100.432 (1)°
Mr = 391.45V = 967.71 (2) Å3
Triclinic, P1Z = 2
a = 9.1387 (1) ÅMo Kα radiation
b = 9.7188 (1) ŵ = 0.09 mm1
c = 11.7006 (2) ÅT = 100 K
α = 90.796 (1)°0.20 × 0.17 × 0.13 mm
β = 108.274 (1)°
Data collection top
Bruker SMART APEXII CCD area-detector
diffractometer
5637 independent reflections
Absorption correction: multi-scan
(SADABS; Bruker, 2005)
4346 reflections with I > 2σ(I)
Tmin = 0.982, Tmax = 0.989Rint = 0.039
27568 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0450 restraints
wR(F2) = 0.129H atoms treated by a mixture of independent and constrained refinement
S = 1.06Δρmax = 0.47 e Å3
5637 reflectionsΔρmin = 0.29 e Å3
275 parameters
Special details top

Experimental. The low-temparture data was collected with the Oxford Cyrosystem Cobra low-temperature attachment.

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
O10.61622 (11)0.27676 (9)0.32200 (8)0.01883 (19)
H1O10.613 (3)0.222 (2)0.250 (2)0.067 (7)*
O20.61815 (11)0.09885 (9)0.16858 (8)0.02066 (19)
O30.75404 (12)0.44307 (10)0.37072 (8)0.0228 (2)
H1O30.712 (2)0.532 (2)0.3441 (18)0.049 (6)*
O40.70875 (10)0.15820 (9)0.72458 (7)0.01672 (18)
N10.76273 (12)0.16662 (10)0.43264 (8)0.0149 (2)
C10.66453 (13)0.22153 (12)0.52648 (10)0.0157 (2)
C20.65150 (13)0.18472 (12)0.40837 (10)0.0152 (2)
C30.67677 (13)0.05172 (12)0.37412 (10)0.0147 (2)
C40.65261 (14)0.01412 (12)0.24907 (10)0.0157 (2)
C50.66192 (13)0.12935 (12)0.21856 (10)0.0160 (2)
C60.61480 (14)0.17997 (13)0.09659 (11)0.0181 (2)
H6A0.58030.12150.03570.022*
C70.61999 (14)0.31638 (13)0.06789 (11)0.0198 (2)
H7A0.59020.34990.01260.024*
C80.66982 (14)0.40457 (13)0.15928 (11)0.0190 (2)
H8A0.67310.49650.13890.023*
C90.71431 (14)0.35751 (12)0.27954 (11)0.0174 (2)
C100.71450 (13)0.21600 (12)0.31109 (10)0.0151 (2)
C110.72382 (13)0.04215 (12)0.46307 (10)0.0147 (2)
C120.73386 (13)0.00910 (12)0.58322 (10)0.0152 (2)
C130.70556 (13)0.12269 (12)0.61097 (10)0.0153 (2)
C140.80949 (14)0.09311 (13)0.82384 (10)0.0172 (2)
C150.77746 (15)0.06229 (13)0.79078 (11)0.0190 (2)
H15A0.77930.12550.84990.023*
C160.74650 (14)0.10879 (12)0.67641 (11)0.0179 (2)
H16A0.73300.20410.65600.021*
C170.76250 (15)0.12599 (14)0.93288 (11)0.0210 (3)
H17A0.65620.07910.92050.032*
H17B0.77030.22540.94390.032*
H17C0.83120.09431.00330.032*
C180.97943 (15)0.16100 (15)0.84190 (12)0.0242 (3)
H18A1.00470.14230.77020.036*
H18B1.04730.12300.90890.036*
H18C0.99360.26050.85800.036*
C190.90568 (14)0.20744 (13)0.51514 (11)0.0196 (2)
H19A0.96260.13160.57490.029*
H19B0.97110.22820.46970.029*
H19C0.87580.28900.55420.029*
C200.64205 (14)0.36238 (12)0.56688 (11)0.0172 (2)
H20A0.58950.40830.49700.021*
H20B0.57620.34890.61820.021*
C210.79840 (14)0.45383 (12)0.63520 (11)0.0183 (2)
H21A0.87470.46410.59720.022*
C220.83977 (16)0.52167 (13)0.74370 (11)0.0216 (3)
C230.73177 (19)0.51901 (16)0.81818 (13)0.0311 (3)
H23A0.65300.43460.79600.047*
H23B0.68210.59900.80390.047*
H23C0.79130.52170.90220.047*
C241.00179 (17)0.60931 (15)0.79955 (13)0.0293 (3)
H24A1.06200.60500.74600.044*
H24B1.05280.57400.87490.044*
H24C0.99390.70490.81340.044*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
O10.0264 (4)0.0139 (4)0.0152 (4)0.0049 (3)0.0045 (3)0.0019 (3)
O20.0294 (5)0.0177 (4)0.0144 (4)0.0057 (3)0.0057 (3)0.0023 (3)
O30.0355 (5)0.0129 (4)0.0186 (4)0.0038 (4)0.0072 (4)0.0010 (3)
O40.0209 (4)0.0173 (4)0.0127 (4)0.0052 (3)0.0056 (3)0.0006 (3)
N10.0195 (5)0.0127 (4)0.0120 (4)0.0042 (4)0.0038 (4)0.0003 (3)
C10.0168 (5)0.0129 (5)0.0167 (5)0.0022 (4)0.0050 (4)0.0002 (4)
C20.0164 (5)0.0127 (5)0.0153 (5)0.0018 (4)0.0040 (4)0.0023 (4)
C30.0167 (5)0.0133 (5)0.0136 (5)0.0017 (4)0.0048 (4)0.0001 (4)
C40.0169 (5)0.0152 (5)0.0142 (5)0.0024 (4)0.0041 (4)0.0011 (4)
C50.0173 (5)0.0157 (5)0.0151 (5)0.0020 (4)0.0059 (4)0.0002 (4)
C60.0194 (5)0.0201 (6)0.0147 (5)0.0039 (4)0.0054 (4)0.0008 (4)
C70.0209 (6)0.0226 (6)0.0153 (5)0.0024 (5)0.0064 (4)0.0040 (4)
C80.0215 (6)0.0157 (5)0.0202 (6)0.0022 (4)0.0082 (5)0.0032 (4)
C90.0197 (5)0.0152 (5)0.0180 (6)0.0030 (4)0.0071 (4)0.0010 (4)
C100.0160 (5)0.0154 (5)0.0139 (5)0.0013 (4)0.0059 (4)0.0005 (4)
C110.0150 (5)0.0123 (5)0.0157 (5)0.0005 (4)0.0047 (4)0.0004 (4)
C120.0176 (5)0.0139 (5)0.0134 (5)0.0025 (4)0.0045 (4)0.0011 (4)
C130.0166 (5)0.0150 (5)0.0138 (5)0.0011 (4)0.0055 (4)0.0004 (4)
C140.0191 (5)0.0186 (6)0.0133 (5)0.0038 (4)0.0044 (4)0.0015 (4)
C150.0245 (6)0.0176 (6)0.0165 (5)0.0059 (5)0.0076 (5)0.0040 (4)
C160.0233 (6)0.0135 (5)0.0175 (6)0.0040 (4)0.0074 (5)0.0020 (4)
C170.0254 (6)0.0224 (6)0.0155 (5)0.0045 (5)0.0070 (5)0.0004 (4)
C180.0199 (6)0.0275 (7)0.0235 (6)0.0025 (5)0.0058 (5)0.0031 (5)
C190.0204 (6)0.0190 (6)0.0177 (6)0.0056 (4)0.0030 (4)0.0001 (4)
C200.0212 (6)0.0154 (5)0.0160 (5)0.0058 (4)0.0061 (4)0.0010 (4)
C210.0220 (6)0.0139 (5)0.0202 (6)0.0047 (4)0.0078 (5)0.0012 (4)
C220.0278 (6)0.0165 (6)0.0198 (6)0.0071 (5)0.0050 (5)0.0009 (4)
C230.0442 (8)0.0300 (7)0.0224 (7)0.0092 (6)0.0145 (6)0.0027 (5)
C240.0314 (7)0.0223 (7)0.0268 (7)0.0057 (5)0.0011 (6)0.0044 (5)
Geometric parameters (Å, º) top
O1—C21.3604 (14)C14—C151.5064 (17)
O1—H1O10.98 (2)C14—C171.5153 (16)
O2—C41.2624 (14)C14—C181.5203 (17)
O3—C91.3610 (15)C15—C161.3321 (16)
O3—H1O30.88 (2)C15—H15A0.93
O4—C131.3588 (13)C16—H16A0.93
O4—C141.4688 (14)C17—H17A0.96
N1—C111.3927 (14)C17—H17B0.96
N1—C101.3995 (14)C17—H17C0.96
N1—C191.4844 (15)C18—H18A0.96
C1—C21.3855 (16)C18—H18B0.96
C1—C131.4019 (16)C18—H18C0.96
C1—C201.5113 (16)C19—H19A0.96
C2—C31.4271 (16)C19—H19B0.96
C3—C111.4099 (16)C19—H19C0.96
C3—C41.4410 (15)C20—C211.5082 (17)
C4—C51.4585 (16)C20—H20A0.97
C5—C101.3993 (17)C20—H20B0.97
C5—C61.4079 (16)C21—C221.3323 (17)
C6—C71.3758 (17)C21—H21A0.93
C6—H6A0.93C22—C231.5050 (19)
C7—C81.3953 (18)C22—C241.5053 (19)
C7—H7A0.93C23—H23A0.96
C8—C91.3823 (16)C23—H23B0.96
C8—H8A0.93C23—H23C0.96
C9—C101.4186 (16)C24—H24A0.96
C11—C121.4085 (15)C24—H24B0.96
C12—C131.4049 (16)C24—H24C0.96
C12—C161.4601 (16)
C2—O1—H1O1101.5 (13)C17—C14—C18111.13 (10)
C9—O3—H1O3110.2 (13)C16—C15—C14119.69 (11)
C13—O4—C14117.12 (9)C16—C15—H15A120.2
C11—N1—C10119.09 (10)C14—C15—H15A120.2
C11—N1—C19117.83 (9)C15—C16—C12119.58 (11)
C10—N1—C19117.58 (9)C15—C16—H16A120.2
C2—C1—C13116.87 (10)C12—C16—H16A120.2
C2—C1—C20123.15 (11)C14—C17—H17A109.5
C13—C1—C20119.95 (10)C14—C17—H17B109.5
O1—C2—C1120.20 (10)H17A—C17—H17B109.5
O1—C2—C3118.25 (10)C14—C17—H17C109.5
C1—C2—C3121.54 (11)H17A—C17—H17C109.5
C11—C3—C2119.55 (10)H17B—C17—H17C109.5
C11—C3—C4120.67 (10)C14—C18—H18A109.5
C2—C3—C4119.77 (11)C14—C18—H18B109.5
O2—C4—C3121.89 (10)H18A—C18—H18B109.5
O2—C4—C5121.25 (10)C14—C18—H18C109.5
C3—C4—C5116.79 (10)H18A—C18—H18C109.5
C10—C5—C6120.80 (11)H18B—C18—H18C109.5
C10—C5—C4119.49 (10)N1—C19—H19A109.5
C6—C5—C4119.70 (11)N1—C19—H19B109.5
C7—C6—C5119.68 (12)H19A—C19—H19B109.5
C7—C6—H6A120.2N1—C19—H19C109.5
C5—C6—H6A120.2H19A—C19—H19C109.5
C6—C7—C8120.11 (11)H19B—C19—H19C109.5
C6—C7—H7A119.9C21—C20—C1110.51 (10)
C8—C7—H7A119.9C21—C20—H20A109.5
C9—C8—C7121.10 (11)C1—C20—H20A109.5
C9—C8—H8A119.5C21—C20—H20B109.5
C7—C8—H8A119.5C1—C20—H20B109.5
O3—C9—C8122.58 (11)H20A—C20—H20B108.1
O3—C9—C10117.72 (10)C22—C21—C20127.50 (12)
C8—C9—C10119.67 (11)C22—C21—H21A116.3
C5—C10—N1121.34 (10)C20—C21—H21A116.3
C5—C10—C9118.58 (10)C21—C22—C23123.88 (12)
N1—C10—C9120.06 (11)C21—C22—C24120.84 (12)
N1—C11—C12119.91 (10)C23—C22—C24115.27 (11)
N1—C11—C3120.07 (10)C22—C23—H23A109.5
C12—C11—C3120.02 (10)C22—C23—H23B109.5
C13—C12—C11117.58 (11)H23A—C23—H23B109.5
C13—C12—C16116.87 (10)C22—C23—H23C109.5
C11—C12—C16124.79 (10)H23A—C23—H23C109.5
O4—C13—C1115.59 (10)H23B—C23—H23C109.5
O4—C13—C12120.03 (10)C22—C24—H24A109.5
C1—C13—C12124.29 (10)C22—C24—H24B109.5
O4—C14—C15108.29 (9)H24A—C24—H24B109.5
O4—C14—C17105.00 (9)C22—C24—H24C109.5
C15—C14—C17112.06 (10)H24A—C24—H24C109.5
O4—C14—C18108.01 (10)H24B—C24—H24C109.5
C15—C14—C18111.99 (10)
C13—C1—C2—O1178.24 (10)C19—N1—C11—C1243.29 (15)
C20—C1—C2—O10.31 (17)C10—N1—C11—C317.49 (16)
C13—C1—C2—C30.75 (17)C19—N1—C11—C3135.73 (11)
C20—C1—C2—C3178.68 (10)C2—C3—C11—N1174.13 (10)
O1—C2—C3—C11175.77 (10)C4—C3—C11—N16.46 (16)
C1—C2—C3—C113.23 (17)C2—C3—C11—C124.89 (16)
O1—C2—C3—C44.81 (16)C4—C3—C11—C12174.52 (10)
C1—C2—C3—C4176.18 (10)N1—C11—C12—C13174.99 (10)
C11—C3—C4—O2176.40 (11)C3—C11—C12—C134.03 (16)
C2—C3—C4—O24.19 (17)N1—C11—C12—C1615.31 (17)
C11—C3—C4—C56.65 (16)C3—C11—C12—C16165.67 (11)
C2—C3—C4—C5172.77 (10)C14—O4—C13—C1155.25 (10)
O2—C4—C5—C10174.13 (11)C14—O4—C13—C1228.13 (15)
C3—C4—C5—C108.89 (16)C2—C1—C13—O4176.40 (10)
O2—C4—C5—C67.23 (17)C20—C1—C13—O45.61 (15)
C3—C4—C5—C6169.75 (10)C2—C1—C13—C120.07 (17)
C10—C5—C6—C70.20 (18)C20—C1—C13—C12177.93 (11)
C4—C5—C6—C7178.42 (11)C11—C12—C13—O4177.89 (10)
C5—C6—C7—C80.82 (18)C16—C12—C13—O47.37 (16)
C6—C7—C8—C90.16 (18)C11—C12—C13—C11.57 (17)
C7—C8—C9—O3175.78 (11)C16—C12—C13—C1168.95 (11)
C7—C8—C9—C102.12 (18)C13—O4—C14—C1548.10 (13)
C6—C5—C10—N1179.53 (10)C13—O4—C14—C17167.97 (9)
C4—C5—C10—N11.85 (17)C13—O4—C14—C1873.37 (12)
C6—C5—C10—C92.12 (17)O4—C14—C15—C1636.03 (15)
C4—C5—C10—C9176.51 (10)C17—C14—C15—C16151.37 (12)
C11—N1—C10—C515.26 (16)C18—C14—C15—C1682.95 (14)
C19—N1—C10—C5138.02 (11)C14—C15—C16—C123.98 (18)
C11—N1—C10—C9163.07 (10)C13—C12—C16—C1519.66 (17)
C19—N1—C10—C943.65 (15)C11—C12—C16—C15170.58 (12)
O3—C9—C10—C5174.94 (10)C2—C1—C20—C21104.52 (13)
C8—C9—C10—C53.06 (17)C13—C1—C20—C2173.35 (14)
O3—C9—C10—N13.43 (16)C1—C20—C21—C22128.12 (13)
C8—C9—C10—N1178.57 (11)C20—C21—C22—C230.7 (2)
C10—N1—C11—C12163.49 (10)C20—C21—C22—C24179.97 (12)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
O1—H1O1···O20.98 (2)1.54 (2)2.4813 (13)160 (2)
O3—H1O3···O1i0.89 (2)1.88 (2)2.7550 (13)167 (2)
C6—H6A···O2ii0.932.553.3636 (15)147
C20—H20A···O10.972.502.8976 (15)105
C18—H18A···Cg1iii0.962.923.3513 (16)109
Symmetry codes: (i) x, y1, z; (ii) x+1, y, z; (iii) x+2, y, z+1.

Experimental details

Crystal data
Chemical formulaC24H25NO4
Mr391.45
Crystal system, space groupTriclinic, P1
Temperature (K)100
a, b, c (Å)9.1387 (1), 9.7188 (1), 11.7006 (2)
α, β, γ (°)90.796 (1), 108.274 (1), 100.432 (1)
V3)967.71 (2)
Z2
Radiation typeMo Kα
µ (mm1)0.09
Crystal size (mm)0.20 × 0.17 × 0.13
Data collection
DiffractometerBruker SMART APEXII CCD area-detector
Absorption correctionMulti-scan
(SADABS; Bruker, 2005)
Tmin, Tmax0.982, 0.989
No. of measured, independent and
observed [I > 2σ(I)] reflections
27568, 5637, 4346
Rint0.039
(sin θ/λ)max1)0.703
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.045, 0.129, 1.06
No. of reflections5637
No. of parameters275
H-atom treatmentH atoms treated by a mixture of independent and constrained refinement
Δρmax, Δρmin (e Å3)0.47, 0.29

Computer programs: APEX2 (Bruker, 2005), APEX2, SAINT (Bruker, 2005), SHELXTL (Sheldrick, 1998), SHELXTL and PLATON (Spek, 2003).

Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
O1—H1O1···O20.98 (2)1.54 (2)2.4813 (13)160 (2)
O3—H1O3···O1i0.89 (2)1.88 (2)2.7550 (13)167 (2)
C6—H6A···O2ii0.932.553.3636 (15)147
C20—H20A···O10.972.502.8976 (15)105
C18—H18A···Cg1iii0.962.923.3513 (16)109
Symmetry codes: (i) x, y1, z; (ii) x+1, y, z; (iii) x+2, y, z+1.
 

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