2(R)-Hydro­xy-4-(4-methoxy­benzoyl)-2-methoxy­carbonyl­methyl-5-(4-methoxy­phenyl)-1-(2-methyl­phenyl)-2,3-di­hydro-1H-3-pyrrolone

Öztürk, S.; Saçmacı, M.; Üngören, H.; Akkurt, M.; Fun, H.-K.; Akçamur, Y.

doi:10.1107/S1600536803011012

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2(R)-Hydroxy-4-(4-methoxybenzoyl)-2-methoxycarbonylmethyl-5-(4-methoxyphenyl)-1-(2-methylphenyl)-2,3-dihydro-1H-3-pyrrolone

S. Öztürk, M. Saçmacı, Ş. H. Üngören, M. Akkurt, H.-K. Fun and Y. Akçamur

The title compound, C₂₉H₂₇NO₇, has a non-planar configuration. The methoxycarbonylmethyl group exhibits an E configuration. The crystal structure is stabilized by intermolecular O—H

O and C—H

O contacts.

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Supporting information

	Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536803011012/cv6194sup1.cif Contains datablocks global, I
	Structure factor file (CIF format) https://doi.org/10.1107/S1600536803011012/cv6194Isup2.hkl Contains datablock I

CCDC reference: 214856

checkCIF report

Key indicators

Single-crystal X-ray study
T = 293 K
Mean (C-C) = 0.006 Å
R factor = 0.078
wR factor = 0.257
Data-to-parameter ratio = 16.7

checkCIF results

No syntax errors found

ADDSYM reports no extra symmetry


 Alert Level C:



REFLT_03
         From the CIF: _diffrn_reflns_theta_max           27.30
         From the CIF: _reflns_number_total               5384
         TEST2: Reflns within _diffrn_reflns_theta_max
         Count of symmetry unique reflns         5855
         Completeness (_total/calc)             91.96%
          Alert C: < 95% complete

RFACR_01  Alert C The value of the weighted R factor is > 0.25
          Weighted R factor given   0.257

PLAT_213  Alert C Atom C14     has ADP max/min Ratio ...........       3.40 prolate


 0 Alert Level A = Potentially serious problem

 0 Alert Level B = Potential problem

 3 Alert Level C = Please check

Comment top

The title compound, (I), is a derivative of 2,3-dihydro-1H-3-pyrrolone, which exhibits antimicrobiological and pharmacological activity (Koz'minykh et al., 2002). The bond lengths and angles in (I) (Table 1) are within normal ranges (Allen et al., 1987). The methoxycarbonylmethyl group shows an E conformation. Compound (I) consists of four planar rings, viz A, B, C and D (Fig. 1). In pyrrolone ring A, the maximum deviation from planarity is 0.028 (3) Å for C2. The dihedral angles between rings A/B, A/C, A/D, B/C, B/D and C/D are 34.6 (1), 72.0 (2), 74.2 (1), 59.6 (2), 80.3 (1) and 40.1 (2)°, respectively.

The crystal structure of (I) is stabilized by O—H···O and C—H···O intermolecular contacts (Table 2).

Experimental top

A mixture of 4-(4-methoxybenzoyl)-2-[(Z)-methoxycarbonylmethylene]-5- (4-methoxyphenyl)-2,3-dihydro-3-furanone (2.213 g, 5 mmol) and o-toluidine (0.536 g, 5 mmol) in dry benzene (25 ml) was refluxed for 0.5 h. The solid obtained after evaporation of the solvent was recrytstallized from ethanol to give yellow crystals of 2(R)-hydroxy-4-(4-methoxybenzoyl)-2- methoxycarbonylmethyl-5-(4-methoxyphenyl)-1-(2-methylphenyl)-2,3-dihydro- 1H-3-pyrrolone; yield: 1.574 g (59%), m.p: 442 K. Solvents were dried by refluxing with the appropriate drying agent and distilled before use. Melting points were determined on an Electrothermal 9200 apparatus and were uncorrected. Elemental analysis was performed with a Carlo Erba Elemental Analyzer 1108. An FT–IR spectrum was measured on a Jasco-Plus Model 460 spectrometer, using a potassium bromide pellet. The ¹H and ¹³C NMR spectra were recorded on a Gemini-Varian 200 MHz instrument. The chemical shifts are reported in p.p.m. from tetramethylsilane and given in d units. FT–IR (KBr, cm⁻¹): ν = 3200.29 (broad OH), 1740.92 (C₂₀═O), 1653.66 (C₂₂═O), 1633.41 (C₂═O), 1257.84 (C₂₀—O₄—C₂₁); ¹H NMR (CDCl₃, p.p.m.): δ = 2.181 (s, 3H, Ph—CH₃), 2.806–3.081 (q, 2H, CH₂), 3.528, 3.666, 3.813 (s, 9H, OCH₃), 5.901 (s, 1H, OH), 6.885–7.942 (m, 12H, Ar—H); ¹³C NMR (CDCl₃, p.p.m.): δ = 20.895 (C₁₈), 41.927 (C₁₉), 54.230, 57.180, 57.384 (C₂₁, C₂₉ and C₁₁), 92.432 (C₁), 110.032–165.105 (C═C, aromatic and aliphatic), 181.055 (C₂₀═O), 190.213 (C₂₂═O), 198.213 (C₂═O). Analysis calculated for C₃₁H₃₅NO₇: C 69.78, N 2.62, H 6.61%; found: C 69.65, N 2.56, H 6.59%.

Computing details top

Data collection: SMART (Siemens, 1996); cell refinement: SAINT (Siemens, 1996); data reduction: SAINT; program(s) used to solve structure: SIR97 (Altomare et al., 1999); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997); software used to prepare material for publication: PARST (Nardelli, 1995) and WinGX (Farrugia, 1999).

Figures top

Fig. 1. An ORTEP drawing of (I), showing the labelling of the non-H atoms. Displacement ellipsoids are shown at the 10% probability level.

2(R)-Hydroxy-4-(4-methoxybenzoyl)-2-methoxycarbonylmethyl-5-(4-methoxyphenyl)- 1-(2-methylphenyl)-2,3-dihydro-1H-3-pyrrolone top

Crystal data top

C₂₉H₂₇NO₇	Z = 2
M_r = 501.52	F(000) = 528
Triclinic, P1	D_x = 1.287 Mg m⁻³
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 8.948 (5) Å	Cell parameters from 2345 reflections
b = 11.254 (5) Å	θ = 5.7–53.7°
c = 13.724 (5) Å	µ = 0.09 mm⁻¹
α = 110.167 (5)°	T = 293 K
β = 93.755 (5)°	Block, yellow
γ = 90.106 (5)°	0.28 × 0.24 × 0.18 mm
V = 1294.1 (10) Å³

Data collection top

Siemens SMART CCD area-detector diffractometer	5384 independent reflections
Radiation source: fine-focus sealed tube	2742 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.000
Detector resolution: 8.33 pixels mm^-1	θ_max = 27.3°, θ_min = 2.9°
ω scans	h = −11→11
Absorption correction: part of the refinement model (ΔF) (Parkin et al., 1995) Cubic fit to sin(theta)/lambda - 24 parameters	k = −15→14
T_min = 0.975, T_max = 0.984	l = 0→18
5384 measured reflections

Refinement top

Refinement on F²	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F² > 2σ(F²)] = 0.078	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.257	H atoms treated by a mixture of independent and constrained refinement
S = 1.00	w = 1/[σ²(F_o²) + (0.1411P)²] where P = (F_o² + 2F_c²)/3
5384 reflections	(Δ/σ)_max < 0.001
322 parameters	Δρ_max = 0.54 e Å⁻³
1 restraint	Δρ_min = −0.29 e Å⁻³

Crystal data top

C₂₉H₂₇NO₇	γ = 90.106 (5)°
M_r = 501.52	V = 1294.1 (10) Å³
Triclinic, P1	Z = 2
a = 8.948 (5) Å	Mo Kα radiation
b = 11.254 (5) Å	µ = 0.09 mm⁻¹
c = 13.724 (5) Å	T = 293 K
α = 110.167 (5)°	0.28 × 0.24 × 0.18 mm
β = 93.755 (5)°

Data collection top

Siemens SMART CCD area-detector diffractometer	5384 independent reflections
Absorption correction: part of the refinement model (ΔF) (Parkin et al., 1995) Cubic fit to sin(theta)/lambda - 24 parameters	2742 reflections with I > 2σ(I)
T_min = 0.975, T_max = 0.984	R_int = 0.000
5384 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.078	1 restraint
wR(F²) = 0.257	H atoms treated by a mixture of independent and constrained refinement
S = 1.00	Δρ_max = 0.54 e Å⁻³
5384 reflections	Δρ_min = −0.29 e Å⁻³
322 parameters

Special details top

Geometry. Bond distances, angles etc. have been calculated using the rounded fractional coordinates. All e.s.d.'s are estimated from the variances of the (full) variance-covariance matrix. The cell e.s.d.'s are taken into account in the estimation of distances, angles and torsion angles

Refinement. Refinement on F^{2 for ALL reflections except those flagged by the user for potential systematic errors. Weighted R-factors wR and all goodnesses of fit S are based on F}2, conventional R-factors R are based on F, with F set to zero for negative F^{2. The observed criterion of F}2 > σ(F^{2) is used only for calculating -R-factor-obs etc. and is not relevant to the choice of reflections for refinement. R-factors based on F}2 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

	x	y	z	U_iso*/U_eq
O1	0.4380 (3)	0.1806 (2)	0.57598 (17)	0.0594 (7)
O2	0.6063 (3)	−0.0214 (2)	0.62095 (18)	0.0609 (8)
O3	0.9095 (3)	0.1478 (4)	0.6198 (2)	0.0851 (13)
O4	0.9314 (4)	0.2001 (4)	0.4803 (2)	0.0956 (13)
O5	0.5549 (4)	0.1283 (3)	0.9223 (2)	0.0759 (10)
O6	1.1126 (4)	−0.2202 (3)	0.8827 (3)	0.0909 (14)
O7	0.8319 (4)	0.6700 (3)	1.1684 (2)	0.0872 (10)
N1	0.6171 (3)	0.3129 (2)	0.6995 (2)	0.0532 (9)
C1	0.5905 (4)	0.1902 (3)	0.6125 (2)	0.0509 (9)
C2	0.6190 (4)	0.0935 (3)	0.6682 (2)	0.0492 (9)
C3	0.6448 (4)	0.1610 (3)	0.7752 (2)	0.0481 (9)
C4	0.6473 (4)	0.2898 (3)	0.7890 (2)	0.0473 (9)
C5	0.6877 (4)	0.3936 (3)	0.8873 (2)	0.0500 (9)
C6	0.7961 (5)	0.3705 (3)	0.9576 (3)	0.0647 (13)
C7	0.8401 (6)	0.4645 (4)	1.0482 (3)	0.0776 (14)
C8	0.7784 (5)	0.5837 (3)	1.0753 (3)	0.0639 (13)
C9	0.6704 (5)	0.6073 (3)	1.0085 (3)	0.0585 (10)
C10	0.6255 (4)	0.5121 (3)	0.9140 (2)	0.0519 (9)
C11	0.7722 (5)	0.7913 (4)	1.2006 (3)	0.0764 (14)
C12	0.6365 (5)	0.4284 (3)	0.6823 (3)	0.0798 (16)
C13	0.7814 (5)	0.4788 (5)	0.6952 (4)	0.179 (5)
C14	0.8067 (10)	0.5951 (6)	0.6839 (5)	0.343 (14)
C15	0.6871 (13)	0.6611 (4)	0.6598 (5)	0.37 (2)
C16	0.5422 (11)	0.6107 (5)	0.6470 (4)	0.307 (14)
C17	0.5169 (6)	0.4944 (5)	0.6582 (3)	0.132 (3)
C18	0.3560 (19)	0.4519 (14)	0.6478 (12)	0.272 (12)
C19	0.6885 (4)	0.1750 (3)	0.5223 (2)	0.0566 (10)
C20	0.8530 (4)	0.1734 (4)	0.5485 (3)	0.0601 (11)
C21	1.0921 (6)	0.1952 (8)	0.4957 (5)	0.121 (3)
C22	0.6474 (4)	0.1019 (3)	0.8568 (2)	0.0550 (10)
C23	0.7651 (4)	0.0096 (3)	0.8561 (2)	0.0545 (10)
C24	0.8909 (4)	0.0055 (3)	0.8011 (3)	0.0579 (11)
C25	1.0093 (5)	−0.0709 (4)	0.8072 (3)	0.0669 (12)
C26	1.0018 (5)	−0.1450 (3)	0.8697 (3)	0.0673 (13)
C27	0.8756 (6)	−0.1441 (3)	0.9221 (3)	0.0715 (14)
C28	0.7586 (5)	−0.0668 (3)	0.9172 (3)	0.0657 (13)
C29	1.2501 (8)	−0.2163 (7)	0.8393 (4)	0.116 (3)
H1	0.42020	0.11070	0.53160	0.0890*
H6	0.83750	0.29090	0.94200	0.0770*
H7	0.91340	0.44860	1.09310	0.0930*
H9	0.62730	0.68640	1.02610	0.0700*
H10	0.55330	0.52860	0.86870	0.0620*
H11A	0.81980	0.84130	1.26690	0.1140*
H11B	0.66650	0.78490	1.20660	0.1140*
H11C	0.78950	0.83080	1.15040	0.1140*
H13	0.86140	0.43470	0.71130	0.2150*
H14	0.90360	0.62880	0.69250	0.4120*
H15	0.70400	0.73890	0.65220	0.4430*
H16	0.46210	0.65490	0.63080	0.3690*
H18A	0.34970	0.37270	0.65950	0.4090*
H18B	0.31400	0.44130	0.57910	0.4090*
H18C	0.30140	0.51430	0.69810	0.4090*
H19A	0.65910	0.09660	0.46650	0.0680*
H19B	0.66910	0.24380	0.49630	0.0680*
H21A	1.13860	0.21820	0.44340	0.1810*
H21B	1.11940	0.11090	0.49060	0.1810*
H21C	1.12510	0.25330	0.56340	0.1810*
H24	0.89570	0.05520	0.75940	0.0690*
H25	1.09300	−0.07290	0.76990	0.0800*
H27	0.86930	−0.19660	0.96130	0.0860*
H28	0.67510	−0.06540	0.95450	0.0790*
H29A	1.31750	−0.27420	0.85560	0.1730*
H29B	1.29290	−0.13210	0.86760	0.1730*
H29C	1.23370	−0.24010	0.76510	0.1730*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
O1	0.0419 (12)	0.0648 (14)	0.0618 (12)	0.0016 (10)	−0.0037 (9)	0.0107 (10)
O2	0.0673 (16)	0.0490 (12)	0.0595 (12)	−0.0034 (11)	−0.0053 (10)	0.0119 (10)
O3	0.0528 (16)	0.136 (3)	0.0833 (17)	−0.0038 (17)	0.0016 (13)	0.0600 (19)
O4	0.0595 (18)	0.156 (3)	0.0871 (19)	−0.0088 (19)	0.0128 (14)	0.061 (2)
O5	0.083 (2)	0.0806 (18)	0.0761 (16)	0.0196 (15)	0.0295 (14)	0.0379 (14)
O6	0.105 (3)	0.0781 (19)	0.096 (2)	0.0341 (18)	0.0042 (18)	0.0386 (17)
O7	0.108 (2)	0.0663 (17)	0.0661 (15)	0.0011 (16)	−0.0221 (15)	0.0010 (13)
N1	0.0563 (17)	0.0504 (14)	0.0506 (13)	−0.0053 (12)	−0.0005 (11)	0.0152 (11)
C1	0.0427 (16)	0.0548 (16)	0.0494 (14)	−0.0060 (13)	−0.0045 (12)	0.0122 (12)
C2	0.0404 (16)	0.0503 (15)	0.0535 (14)	0.0017 (12)	0.0024 (12)	0.0139 (12)
C3	0.0489 (17)	0.0445 (14)	0.0496 (14)	−0.0006 (12)	0.0059 (12)	0.0142 (12)
C4	0.0449 (17)	0.0498 (15)	0.0479 (13)	−0.0027 (13)	0.0051 (11)	0.0173 (12)
C5	0.0530 (18)	0.0471 (15)	0.0481 (14)	−0.0057 (13)	0.0037 (12)	0.0140 (12)
C6	0.075 (3)	0.0508 (17)	0.0612 (18)	0.0028 (17)	−0.0086 (16)	0.0127 (14)
C7	0.093 (3)	0.067 (2)	0.062 (2)	0.002 (2)	−0.0184 (19)	0.0128 (17)
C8	0.075 (3)	0.0525 (18)	0.0591 (18)	−0.0093 (17)	0.0030 (16)	0.0132 (15)
C9	0.071 (2)	0.0453 (15)	0.0603 (17)	−0.0029 (15)	0.0112 (15)	0.0184 (13)
C10	0.0573 (19)	0.0450 (14)	0.0523 (15)	−0.0023 (13)	0.0010 (13)	0.0159 (12)
C11	0.084 (3)	0.065 (2)	0.062 (2)	−0.010 (2)	0.0057 (18)	−0.0011 (16)
C12	0.123 (4)	0.059 (2)	0.059 (2)	−0.018 (2)	0.011 (2)	0.0216 (17)
C13	0.284 (12)	0.142 (6)	0.086 (4)	−0.112 (7)	0.077 (5)	−0.005 (4)
C14	0.61 (4)	0.223 (13)	0.139 (8)	−0.280 (19)	0.113 (14)	−0.026 (9)
C15	0.83 (6)	0.172 (12)	0.126 (9)	−0.02 (2)	0.122 (19)	0.059 (9)
C16	0.70 (4)	0.149 (9)	0.109 (6)	0.184 (18)	0.131 (13)	0.071 (7)
C17	0.223 (9)	0.098 (4)	0.080 (3)	0.053 (5)	0.025 (4)	0.036 (3)
C18	0.37 (3)	0.215 (13)	0.211 (14)	0.079 (15)	−0.034 (15)	0.057 (11)
C19	0.0533 (19)	0.0662 (19)	0.0510 (15)	−0.0006 (15)	0.0027 (13)	0.0213 (14)
C20	0.051 (2)	0.073 (2)	0.0582 (17)	−0.0021 (16)	0.0108 (14)	0.0240 (16)
C21	0.061 (3)	0.195 (7)	0.132 (5)	−0.002 (4)	0.026 (3)	0.086 (5)
C22	0.064 (2)	0.0459 (15)	0.0535 (15)	−0.0033 (14)	0.0045 (14)	0.0152 (13)
C23	0.067 (2)	0.0456 (15)	0.0506 (15)	−0.0004 (14)	0.0022 (14)	0.0165 (12)
C24	0.058 (2)	0.0580 (18)	0.0630 (17)	0.0027 (15)	0.0070 (15)	0.0271 (15)
C25	0.065 (2)	0.068 (2)	0.071 (2)	0.0058 (18)	0.0078 (17)	0.0276 (17)
C26	0.080 (3)	0.0515 (18)	0.0660 (19)	0.0133 (18)	−0.0021 (18)	0.0161 (15)
C27	0.097 (3)	0.0544 (19)	0.071 (2)	0.0111 (19)	0.010 (2)	0.0310 (17)
C28	0.083 (3)	0.0556 (19)	0.0631 (18)	0.0005 (18)	0.0118 (17)	0.0253 (16)
C29	0.109 (5)	0.141 (5)	0.097 (3)	0.062 (4)	0.013 (3)	0.040 (3)

Geometric parameters (Å, º) top

O1—C1	1.413 (4)	C22—C23	1.479 (5)
O2—C2	1.232 (4)	C23—C28	1.396 (5)
O3—C20	1.194 (5)	C23—C24	1.388 (5)
O4—C20	1.318 (5)	C24—C25	1.382 (6)
O4—C21	1.444 (7)	C25—C26	1.391 (6)
O5—C22	1.223 (4)	C26—C27	1.376 (7)
O6—C26	1.347 (6)	C27—C28	1.375 (6)
O6—C29	1.409 (8)	C6—H6	0.9300
O7—C8	1.367 (5)	C7—H7	0.9303
O7—C11	1.401 (6)	C9—H9	0.9299
O1—H1	0.8195	C10—H10	0.9305
N1—C4	1.351 (4)	C11—H11A	0.9598
N1—C12	1.411 (4)	C11—H11B	0.9595
N1—C1	1.488 (4)	C11—H11C	0.9597
C1—C2	1.544 (5)	C13—H13	0.9294
C1—C19	1.526 (4)	C14—H14	0.9296
C2—C3	1.404 (4)	C15—H15	0.9300
C3—C4	1.396 (5)	C16—H16	0.9313
C3—C22	1.486 (4)	C18—H18A	0.9608
C4—C5	1.471 (4)	C18—H18B	0.9593
C5—C10	1.384 (5)	C18—H18C	0.9589
C5—C6	1.411 (5)	C19—H19A	0.9701
C6—C7	1.359 (6)	C19—H19B	0.9695
C7—C8	1.389 (6)	C21—H21A	0.9603
C8—C9	1.378 (6)	C21—H21B	0.9602
C9—C10	1.401 (5)	C21—H21C	0.9604
C12—C17	1.3901	C24—H24	0.9306
C12—C13	1.3900	C25—H25	0.9305
C13—C14	1.3899	C27—H27	0.9299
C14—C15	1.3901	C28—H28	0.9301
C15—C16	1.3901	C29—H29A	0.9605
C16—C17	1.3893	C29—H29B	0.9596
C17—C18	1.498 (18)	C29—H29C	0.9605
C19—C20	1.494 (5)

O1···O2	2.945 (4)	C4···H11B^vi	2.9399
O1···C17	3.374 (6)	C9···H11C	2.7560
O1···C18	2.977 (17)	C9···H27^vii	3.0951
O1···C21ⁱ	3.240 (6)	C9···H11B	2.7665
O1···O2ⁱⁱ	2.681 (4)	C11···H9	2.5393
O2···C19ⁱⁱ	3.282 (5)	C12···H19B	2.7130
O2···O1	2.945 (4)	C12···H10	2.5756
O2···C23	3.343 (4)	C15···H21A^x	2.8092
O2···C24	3.368 (5)	C15···H18B^xi	3.0771
O2···O1ⁱⁱ	2.681 (4)	C17···H10	2.7766
O3···C3	3.260 (5)	C18···H21Cⁱ	2.9138
O3···C24	3.404 (6)	C20···H21B^iv	3.0696
O3···C2	2.841 (5)	C20···H13	3.0153
O3···N1	3.238 (5)	C21···H15^x	3.0849
O3···C4	3.409 (5)	C22···H6	2.6069
O5···C5	3.407 (5)	C23···H6	3.0250
O5···C6	3.355 (6)	C25···H29B	2.7795
O6···C6ⁱⁱⁱ	3.265 (6)	C25···H29C	2.7201
O6···C7ⁱⁱⁱ	3.223 (6)	C26···H14^ix	2.9342
O1···H18A	2.2424	C28···H29Bⁱⁱⁱ	3.0934
O2···H1ⁱⁱ	1.9831	C29···H18C^xii	3.0378
O2···H19Aⁱⁱ	2.5914	C29···H25	2.5260
O2···H1	2.7360	H1···O2	2.7360
O3···H21C	2.5596	H1···H19A	2.3551
O3···H21B^iv	2.7826	H1···O2ⁱⁱ	1.9831
O3···H21B	2.6030	H1···C2ⁱⁱ	2.9067
O3···H11A^v	2.7702	H1···H19Aⁱⁱ	2.4464
O3···H24	2.4858	H6···C3	2.7417
O5···H9^vi	2.5795	H6···C22	2.6069
O5···H28	2.5913	H6···C23	3.0250
O6···H6ⁱⁱⁱ	2.7930	H6···O6ⁱⁱⁱ	2.7930
O6···H7ⁱⁱⁱ	2.7144	H7···O6ⁱⁱⁱ	2.7144
N1···O3	3.238 (5)	H9···C11	2.5393
N1···H10	2.8112	H9···H11B	2.3409
N1···H18A	2.5628	H9···H11C	2.3266
C1···C18	3.533 (17)	H9···O5^vi	2.5795
C2···O3	2.841 (5)	H10···N1	2.8112
C2···C24	3.302 (5)	H10···C12	2.5756
C3···O3	3.260 (5)	H10···C17	2.7766
C4···O3	3.409 (5)	H11A···O3^v	2.7702
C5···C9^vi	3.595 (6)	H11B···C9	2.7665
C5···C13	3.256 (6)	H11B···H9	2.3409
C5···O5	3.407 (5)	H11B···C3^vi	2.8609
C6···O5	3.355 (6)	H11B···C4^vi	2.9399
C6···C22	3.112 (5)	H11C···C9	2.7560
C6···O6ⁱⁱⁱ	3.265 (6)	H11C···H9	2.3266
C7···C7^v	3.434 (7)	H13···C4	2.9869
C7···O6ⁱⁱⁱ	3.223 (6)	H13···C20	3.0153
C9···C5^vi	3.595 (6)	H14···C26^vii	2.9342
C9···C10^vi	3.360 (6)	H15···C21^x	3.0849
C10···C13	3.298 (6)	H15···H21A^x	2.1481
C10···C10^vi	3.439 (5)	H16···H18B	2.5937
C10···C17	3.518 (5)	H16···H18C	2.5686
C10···C9^vi	3.360 (6)	H18A···O1	2.2424
C10···C12	2.997 (5)	H18A···N1	2.5628
C12···C10	2.997 (5)	H18A···C1	2.9261
C12···C20	3.495 (6)	H18A···H21Cⁱ	2.4505
C13···C19	3.485 (7)	H18B···H16	2.5937
C13···C5	3.256 (6)	H18B···C15^xi	3.0771
C13···C20	3.418 (7)	H18C···C29^xiii	3.0378
C13···C10	3.298 (6)	H18C···H16	2.5686
C14···C26^vii	3.516 (8)	H19A···H1	2.3551
C14···C27^vii	3.577 (8)	H19A···O2ⁱⁱ	2.5914
C17···O1	3.374 (6)	H19A···H1ⁱⁱ	2.4464
C17···C10	3.518 (5)	H19B···C12	2.7130
C18···C1	3.533 (17)	H21A···C15^x	2.8092
C18···O1	2.977 (17)	H21A···H15^x	2.1481
C19···O2ⁱⁱ	3.282 (5)	H21B···O3	2.6030
C19···C13	3.485 (7)	H21B···O3^iv	2.7826
C20···C12	3.495 (6)	H21B···C20^iv	3.0696
C20···C13	3.418 (7)	H21C···O3	2.5596
C21···O1^viii	3.240 (6)	H21C···C18^viii	2.9138
C22···C6	3.112 (5)	H21C···H18A^viii	2.4505
C23···O2	3.343 (4)	H24···O3	2.4858
C24···O2	3.368 (5)	H24···C2	2.8022
C24···C2	3.302 (5)	H24···C3	2.5299
C24···O3	3.404 (6)	H25···C29	2.5260
C26···C14^ix	3.516 (8)	H25···H29B	2.3974
C27···C14^ix	3.577 (8)	H25···H29C	2.2504
C1···H18A	2.9261	H27···C9^ix	3.0951
C2···H24	2.8022	H28···O5	2.5913
C2···H1ⁱⁱ	2.9067	H29B···C25	2.7795
C3···H24	2.5299	H29B···H25	2.3974
C3···H11B^vi	2.8609	H29B···C28ⁱⁱⁱ	3.0934
C3···H6	2.7417	H29C···C25	2.7201
C4···H13	2.9869	H29C···H25	2.2504

C20—O4—C21	115.9 (4)	C25—C26—C27	119.8 (4)
C26—O6—C29	119.2 (4)	C26—C27—C28	120.9 (4)
C8—O7—C11	118.6 (3)	C23—C28—C27	120.0 (4)
C1—O1—H1	109.54	C5—C6—H6	120.02
C1—N1—C4	109.0 (2)	C7—C6—H6	119.93
C1—N1—C12	122.3 (3)	C6—C7—H7	119.19
C4—N1—C12	127.6 (3)	C8—C7—H7	119.21
O1—C1—C2	108.7 (3)	C8—C9—H9	120.02
O1—C1—C19	109.4 (2)	C10—C9—H9	119.99
O1—C1—N1	108.6 (3)	C5—C10—H10	119.62
N1—C1—C19	113.3 (3)	C9—C10—H10	119.80
C2—C1—C19	114.5 (3)	O7—C11—H11A	109.45
N1—C1—C2	102.0 (2)	O7—C11—H11B	109.48
O2—C2—C3	130.1 (3)	O7—C11—H11C	109.45
C1—C2—C3	108.0 (3)	H11A—C11—H11B	109.45
O2—C2—C1	121.6 (2)	H11A—C11—H11C	109.47
C2—C3—C4	107.7 (3)	H11B—C11—H11C	109.51
C2—C3—C22	124.1 (3)	C12—C13—H13	120.01
C4—C3—C22	127.8 (2)	C14—C13—H13	119.98
N1—C4—C3	113.1 (2)	C13—C14—H14	120.01
N1—C4—C5	121.0 (3)	C15—C14—H14	119.98
C3—C4—C5	125.7 (3)	C14—C15—H15	120.03
C4—C5—C10	123.5 (3)	C16—C15—H15	120.01
C6—C5—C10	118.6 (3)	C15—C16—H16	119.94
C4—C5—C6	117.9 (3)	C17—C16—H16	120.02
C5—C6—C7	120.1 (4)	C17—C18—H18A	109.45
C6—C7—C8	121.6 (4)	C17—C18—H18B	109.43
O7—C8—C7	116.0 (4)	C17—C18—H18C	109.49
C7—C8—C9	119.2 (4)	H18A—C18—H18B	109.47
O7—C8—C9	124.8 (4)	H18A—C18—H18C	109.49
C8—C9—C10	120.0 (3)	H18B—C18—H18C	109.51
C5—C10—C9	120.6 (3)	C1—C19—H19A	108.54
N1—C12—C13	117.4 (4)	C1—C19—H19B	108.59
N1—C12—C17	122.6 (4)	C20—C19—H19A	108.49
C13—C12—C17	119.98	C20—C19—H19B	108.50
C12—C13—C14	120.00	H19A—C19—H19B	107.52
C13—C14—C15	120.01	O4—C21—H21A	109.42
C14—C15—C16	119.96	O4—C21—H21B	109.48
C15—C16—C17	120.04	O4—C21—H21C	109.45
C12—C17—C16	120.00	H21A—C21—H21B	109.53
C12—C17—C18	124.3 (8)	H21A—C21—H21C	109.51
C16—C17—C18	115.6 (8)	H21B—C21—H21C	109.43
C1—C19—C20	115.0 (3)	C23—C24—H24	119.40
O3—C20—O4	122.9 (4)	C25—C24—H24	119.36
O4—C20—C19	111.5 (3)	C24—C25—H25	120.44
O3—C20—C19	125.6 (4)	C26—C25—H25	120.35
O5—C22—C23	121.0 (3)	C26—C27—H27	119.51
C3—C22—C23	117.9 (3)	C28—C27—H27	119.54
O5—C22—C3	121.1 (3)	C23—C28—H28	119.94
C22—C23—C28	121.1 (3)	C27—C28—H28	120.09
C24—C23—C28	118.8 (3)	O6—C29—H29A	109.42
C22—C23—C24	120.0 (3)	O6—C29—H29B	109.52
C23—C24—C25	121.2 (4)	O6—C29—H29C	109.50
C24—C25—C26	119.2 (4)	H29A—C29—H29B	109.45
O6—C26—C25	123.7 (4)	H29A—C29—H29C	109.46
O6—C26—C27	116.5 (4)	H29B—C29—H29C	109.47

C21—O4—C20—O3	0.8 (7)	N1—C4—C5—C10	36.5 (5)
C21—O4—C20—C19	−177.2 (5)	C3—C4—C5—C6	32.5 (5)
C29—O6—C26—C27	−174.0 (4)	C3—C4—C5—C10	−147.7 (4)
C29—O6—C26—C25	6.2 (6)	N1—C4—C5—C6	−143.3 (4)
C11—O7—C8—C9	1.2 (6)	C6—C5—C10—C9	0.6 (5)
C11—O7—C8—C7	−179.0 (4)	C10—C5—C6—C7	−1.6 (6)
C12—N1—C1—C2	165.6 (3)	C4—C5—C6—C7	178.2 (4)
C4—N1—C12—C13	62.2 (5)	C4—C5—C10—C9	−179.2 (3)
C12—N1—C4—C5	8.6 (5)	C5—C6—C7—C8	1.5 (7)
C1—N1—C12—C17	79.2 (5)	C6—C7—C8—C9	−0.3 (7)
C1—N1—C12—C13	−103.8 (4)	C6—C7—C8—O7	179.9 (4)
C12—N1—C1—O1	−79.7 (4)	C7—C8—C9—C10	−0.8 (6)
C1—N1—C4—C3	−0.1 (4)	O7—C8—C9—C10	179.0 (4)
C4—N1—C1—O1	111.9 (3)	C8—C9—C10—C5	0.6 (6)
C12—N1—C1—C19	42.0 (4)	C13—C12—C17—C18	−176.9 (8)
C4—N1—C1—C19	−126.3 (3)	C13—C12—C17—C16	0.00
C4—N1—C1—C2	−2.7 (3)	N1—C12—C17—C18	0.0 (9)
C4—N1—C12—C17	−114.7 (4)	N1—C12—C13—C14	−177.1 (5)
C12—N1—C4—C3	−167.7 (3)	N1—C12—C17—C16	176.9 (4)
C1—N1—C4—C5	176.1 (3)	C17—C12—C13—C14	−0.07
C19—C1—C2—O2	−57.9 (4)	C12—C13—C14—C15	0.07
O1—C1—C2—O2	64.7 (4)	C13—C14—C15—C16	0.00
O1—C1—C2—C3	−109.9 (3)	C14—C15—C16—C17	−0.05
N1—C1—C2—O2	179.3 (3)	C15—C16—C17—C12	0.04
C19—C1—C2—C3	127.4 (3)	C15—C16—C17—C18	177.2 (8)
C2—C1—C19—C20	−53.3 (4)	C1—C19—C20—O4	−160.1 (3)
N1—C1—C2—C3	4.7 (4)	C1—C19—C20—O3	22.0 (6)
N1—C1—C19—C20	63.1 (4)	C3—C22—C23—C28	−168.0 (3)
O1—C1—C19—C20	−175.6 (3)	O5—C22—C23—C24	−162.7 (3)
O2—C2—C3—C22	−6.4 (6)	O5—C22—C23—C28	11.7 (5)
C1—C2—C3—C22	167.7 (3)	C3—C22—C23—C24	17.5 (4)
C1—C2—C3—C4	−4.9 (4)	C22—C23—C24—C25	173.6 (3)
O2—C2—C3—C4	−179.0 (4)	C24—C23—C28—C27	0.1 (5)
C4—C3—C22—C23	−125.4 (4)	C22—C23—C28—C27	−174.4 (3)
C4—C3—C22—O5	54.8 (5)	C28—C23—C24—C25	−1.0 (5)
C22—C3—C4—C5	15.1 (6)	C23—C24—C25—C26	0.0 (6)
C2—C3—C22—O5	−116.2 (4)	C24—C25—C26—O6	−178.4 (4)
C2—C3—C4—N1	3.3 (4)	C24—C25—C26—C27	1.8 (6)
C22—C3—C4—N1	−168.9 (3)	C25—C26—C27—C28	−2.7 (6)
C2—C3—C22—C23	63.5 (5)	O6—C26—C27—C28	177.5 (4)
C2—C3—C4—C5	−172.7 (3)	C26—C27—C28—C23	1.8 (6)

Symmetry codes: (i) x−1, y, z; (ii) −x+1, −y, −z+1; (iii) −x+2, −y, −z+2; (iv) −x+2, −y, −z+1; (v) −x+2, −y+1, −z+2; (vi) −x+1, −y+1, −z+2; (vii) x, y+1, z; (viii) x+1, y, z; (ix) x, y−1, z; (x) −x+2, −y+1, −z+1; (xi) −x+1, −y+1, −z+1; (xii) x+1, y−1, z; (xiii) x−1, y+1, z.

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O1—H1···O2ⁱⁱ	0.82	1.98	2.681 (4)	143
C9—H9···O5^vi	0.93	2.58	3.485 (6)	165
C18—H18A···O1	0.96	2.24	2.977 (17)	132
C18—H18A···N1	0.96	2.56	2.995 (17)	107
C19—H19A···O2ⁱⁱ	0.97	2.59	3.282 (5)	128
C24—H24···O3	0.93	2.49	3.404 (6)	169

Symmetry codes: (ii) −x+1, −y, −z+1; (vi) −x+1, −y+1, −z+2.

Experimental details

Crystal data
Chemical formula	C₂₉H₂₇NO₇
M_r	501.52
Crystal system, space group	Triclinic, P1
Temperature (K)	293
a, b, c (Å)	8.948 (5), 11.254 (5), 13.724 (5)
α, β, γ (°)	110.167 (5), 93.755 (5), 90.106 (5)
V (Å³)	1294.1 (10)
Z	2
Radiation type	Mo Kα
µ (mm⁻¹)	0.09
Crystal size (mm)	0.28 × 0.24 × 0.18

Data collection
Diffractometer	Siemens SMART CCD area-detector diffractometer
Absorption correction	Part of the refinement model (ΔF) (Parkin et al., 1995) Cubic fit to sin(theta)/lambda - 24 parameters
T_min, T_max	0.975, 0.984
No. of measured, independent and observed [I > 2σ(I)] reflections	5384, 5384, 2742
R_int	0.000
(sin θ/λ)_max (Å⁻¹)	0.645

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.078, 0.257, 1.00
No. of reflections	5384
No. of parameters	322
No. of restraints	1
H-atom treatment	H atoms treated by a mixture of independent and constrained refinement
Δρ_max, Δρ_min (e Å⁻³)	0.54, −0.29

Computer programs: SMART (Siemens, 1996), SAINT (Siemens, 1996), SAINT, SIR97 (Altomare et al., 1999), SHELXL97 (Sheldrick, 1997), ORTEP-3 for Windows (Farrugia, 1997), PARST (Nardelli, 1995) and WinGX (Farrugia, 1999).

Selected geometric parameters (Å, º) top

O1—C1	1.413 (4)	O6—C29	1.409 (8)
O2—C2	1.232 (4)	O7—C8	1.367 (5)
O3—C20	1.194 (5)	O7—C11	1.401 (6)
O4—C20	1.318 (5)	N1—C4	1.351 (4)
O4—C21	1.444 (7)	N1—C12	1.411 (4)
O5—C22	1.223 (4)	N1—C1	1.488 (4)
O6—C26	1.347 (6)

C20—O4—C21	115.9 (4)	N1—C4—C3	113.1 (2)
C26—O6—C29	119.2 (4)	N1—C4—C5	121.0 (3)
C8—O7—C11	118.6 (3)	O7—C8—C7	116.0 (4)
C1—N1—C4	109.0 (2)	O7—C8—C9	124.8 (4)
C1—N1—C12	122.3 (3)	N1—C12—C13	117.4 (4)
C4—N1—C12	127.6 (3)	N1—C12—C17	122.6 (4)
O1—C1—C2	108.7 (3)	O3—C20—O4	122.9 (4)
O1—C1—C19	109.4 (2)	O4—C20—C19	111.5 (3)
O1—C1—N1	108.6 (3)	O3—C20—C19	125.6 (4)
N1—C1—C19	113.3 (3)	O5—C22—C23	121.0 (3)
N1—C1—C2	102.0 (2)	O5—C22—C3	121.1 (3)
O2—C2—C3	130.1 (3)	O6—C26—C25	123.7 (4)
O2—C2—C1	121.6 (2)	O6—C26—C27	116.5 (4)

C21—O4—C20—O3	0.8 (7)	O1—C1—C2—O2	64.7 (4)
C21—O4—C20—C19	−177.2 (5)	O1—C1—C2—C3	−109.9 (3)
C4—N1—C1—O1	111.9 (3)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O1—H1···O2ⁱ	0.82	1.98	2.681 (4)	143
C9—H9···O5ⁱⁱ	0.93	2.58	3.485 (6)	165
C19—H19A···O2ⁱ	0.97	2.59	3.282 (5)	128

Symmetry codes: (i) −x+1, −y, −z+1; (ii) −x+1, −y+1, −z+2.

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