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In the title compound, C34H34N4O11·C4H8O2, the dihydro­pyridine rings display envelope configuration. The solvent mol­ecule links to the anhydride via weak C—H...O hydrogen bonding.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536805039772/xu6072sup1.cif
Contains datablocks global, I

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536805039772/xu6072Isup2.hkl
Contains datablock I

CCDC reference: 296732

Key indicators

  • Single-crystal X-ray study
  • T = 293 K
  • Mean [sigma](C-C) = 0.005 Å
  • R factor = 0.065
  • wR factor = 0.206
  • Data-to-parameter ratio = 13.8

checkCIF/PLATON results

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Alert level C PLAT199_ALERT_1_C Check the Reported _cell_measurement_temperature 293 K PLAT200_ALERT_1_C Check the Reported _diffrn_ambient_temperature . 293 K PLAT220_ALERT_2_C Large Non-Solvent C Ueq(max)/Ueq(min) ... 2.94 Ratio PLAT220_ALERT_2_C Large Non-Solvent O Ueq(max)/Ueq(min) ... 2.97 Ratio PLAT222_ALERT_3_C Large Non-Solvent H Ueq(max)/Ueq(min) ... 3.45 Ratio PLAT242_ALERT_2_C Check Low Ueq as Compared to Neighbors for N2 PLAT242_ALERT_2_C Check Low Ueq as Compared to Neighbors for N4 PLAT244_ALERT_4_C Low 'Solvent' Ueq as Compared to Neighbors for C36 PLAT250_ALERT_2_C Large U3/U1 Ratio for Average U(i,j) Tensor .... 2.19 PLAT340_ALERT_3_C Low Bond Precision on C-C bonds (x 1000) Ang ... 5 PLAT360_ALERT_2_C Short C(sp3)-C(sp3) Bond C37 - C38 ... 1.35 Ang.
0 ALERT level A = In general: serious problem 0 ALERT level B = Potentially serious problem 11 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 6 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 1 ALERT type 4 Improvement, methodology, query or suggestion

Comment top

4-Aryl-1,4-dihydropyridine-3,5-dicarboxylic diesters of the nefidipine type have become almost indispensable for the treatment of cardiovascular diseases since they first appeared on the market in 1975 (Yiu & Edward, 1999; Goldmann & Stoltefuss, 1991). The title compound, (I), is related to the preparation of the above compounds.

The molecular structure of (I) is shown in Fig. 1. Both dihydropyridine rings display the envelope configuration, with atoms C10 and C28 displaced from the mean planes formed by the other atoms in the same ring by 0.287 (1) and 0.217 (1) Å, respectively. The dihedral angle between the C11-containing benzene ring and the N1/C4/C5/C7/C9 plane is 87.42 (5)°, while the dihedral angle between the C29-containing benzene ring and the N3/C19/C20/C22/C24 plane is 85.04 (5)°. This is comparable to the situation found in nefidipine (Hofmann & Cimiraglia, 1990; Ramusino & Varì, 1999). The C17—O6 and C18—O6 bond distances (Table 1) are much longer than the C17—O5 and C18—O7 bond distances, respectively, and show the single-bond feature.

Both classic N—H···O and weak C—H···O hydrogen bonds occur in the crystal structure (Table 2). The solvent molecule links with the anhydride via weak C—H···O hydrogen bonding.

Experimental top

5-Ethoxycarbonyl-2,6-dimethyl-4-(3-nitrophenyl)-1,4-dihydropyridine- 3-carboxylic acid (0.45 g, 1 mmol) was dissolved in CH2Cl2 (30 ml), and dicyclohexylcarbodiimide (0.21 g, 1 mmol) in CH2Cl2 (10 ml) was dropped into the above solution at 278 K. The reaction mixture was stirred at 276–279 K for 4 h. The solvent CH2Cl2 was removed by vacuum evaporation at 293 K. The destination compound was purified by chromatography on a silica gel column (eluted by ethyl acetate and petroleum, 3:7) at room temperature. The product (0.41 g) was obtained in a yield of 94%. Recrystallization from a dichloromethane/ethyl acetate solution gave single crystals of (I).

Refinement top

Methyl H atoms were placed in calculated positions with C—H = 0.96 Å and torsion refined to fit the electron density with Uiso(H) = 1.5Ueq(C). Other H atoms were placed in calculated positions with C—H = 0.93–0.98 Å and N—H = 0.86 Å, and constrained to ride on their parent atoms with Uiso(H) = 1.2Ueq(carrier).

Computing details top

Data collection: PROCESS-AUTO (Rigaku, 1998); cell refinement: PROCESS-AUTO; data reduction: CrystalStructure (Rigaku/MSC, 2002); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: SHELXTL (Bruker, 2002); software used to prepare material for publication: SHELXTL.

Figures top
[Figure 1] Fig. 1. The molecular structure of (I), with 30% probability displacement ellipsoids. H atoms are shown as small spheres of arbitrary radii.
5-Ethoxycarbonyl-2,6-dimethyl-4-(3-nitrophenyl)-1,4-dihydro-pyridine- 3-carboxylic anhydride ethyl acetate solvate top
Crystal data top
C34H34N4O11·C4H8O2Z = 2
Mr = 762.76F(000) = 804
Triclinic, P1Dx = 1.342 Mg m3
Hall symbol: -P 1Melting point = 450–451 K
a = 10.896 (2) ÅMo Kα radiation, λ = 0.71073 Å
b = 12.017 (2) ÅCell parameters from 15558 reflections
c = 16.162 (3) Åθ = 3.2–25.5°
α = 99.59 (3)°µ = 0.10 mm1
β = 106.29 (3)°T = 293 K
γ = 105.69 (3)°Block, yellow
V = 1887.1 (9) Å30.28 × 0.22 × 0.10 mm
Data collection top
Rigaku R-AXIS RAPID
diffractometer
4362 reflections with I > 2σ(I)
Radiation source: rotating anodeRint = 0.038
Graphite monochromatorθmax = 25.5°, θmin = 3.2°
ω scansh = 1313
18422 measured reflectionsk = 1414
6953 independent reflectionsl = 1919
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)] = 0.065Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.206H-atom parameters constrained
S = 1.08 w = 1/[σ2(Fo2) + (0.1184P)2]
where P = (Fo2 + 2Fc2)/3
6953 reflections(Δ/σ)max = 0.001
504 parametersΔρmax = 0.57 e Å3
0 restraintsΔρmin = 0.45 e Å3
Crystal data top
C34H34N4O11·C4H8O2γ = 105.69 (3)°
Mr = 762.76V = 1887.1 (9) Å3
Triclinic, P1Z = 2
a = 10.896 (2) ÅMo Kα radiation
b = 12.017 (2) ŵ = 0.10 mm1
c = 16.162 (3) ÅT = 293 K
α = 99.59 (3)°0.28 × 0.22 × 0.10 mm
β = 106.29 (3)°
Data collection top
Rigaku R-AXIS RAPID
diffractometer
4362 reflections with I > 2σ(I)
18422 measured reflectionsRint = 0.038
6953 independent reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0650 restraints
wR(F2) = 0.206H-atom parameters constrained
S = 1.08Δρmax = 0.57 e Å3
6953 reflectionsΔρmin = 0.45 e Å3
504 parameters
Special details top

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
O10.3869 (2)0.50900 (18)0.11858 (13)0.0586 (5)
O20.5820 (3)0.6080 (3)0.10492 (19)0.0967 (9)
O30.1157 (3)0.4971 (3)0.4347 (2)0.1420 (15)
O40.0521 (3)0.4272 (3)0.2952 (2)0.0983 (9)
O50.4989 (2)0.1678 (2)0.36098 (16)0.0705 (6)
O60.33349 (17)0.17678 (15)0.24507 (12)0.0479 (4)
O70.2374 (2)0.18901 (19)0.35081 (13)0.0681 (6)
O80.6393 (3)0.1781 (3)0.2608 (2)0.1137 (11)
O90.6059 (3)0.0693 (3)0.1715 (2)0.1117 (11)
O100.0790 (2)0.2303 (2)0.08999 (14)0.0800 (7)
O110.1436 (2)0.14129 (18)0.02035 (12)0.0632 (6)
O120.0855 (5)0.7276 (5)0.3950 (3)0.184 (2)
O130.1371 (4)0.9037 (3)0.4833 (3)0.1408 (14)
N10.7668 (2)0.4367 (2)0.29037 (17)0.0590 (6)
H1D0.85350.45870.31530.071*
N20.1399 (3)0.4761 (2)0.3657 (2)0.0704 (8)
N30.1162 (2)0.0783 (2)0.15706 (15)0.0537 (6)
H3A0.19050.10240.16790.064*
N40.5678 (3)0.1315 (3)0.2177 (2)0.0774 (8)
C10.1708 (4)0.5116 (4)0.0361 (3)0.0974 (13)
H1A0.12280.54430.00740.146*
H1B0.15550.53400.09120.146*
H1C0.13880.42580.01480.146*
C20.3182 (4)0.5589 (3)0.0511 (2)0.0726 (9)
H2A0.33510.53560.00400.087*
H2B0.35130.64570.07140.087*
C30.5221 (3)0.5391 (3)0.13875 (19)0.0585 (7)
C40.5810 (3)0.4801 (2)0.20378 (17)0.0481 (6)
C50.7152 (3)0.4987 (3)0.23253 (19)0.0537 (7)
C60.8237 (3)0.5814 (3)0.2086 (2)0.0793 (10)
H6A0.78840.63690.18170.119*
H6B0.85080.53520.16710.119*
H6C0.90070.62480.26160.119*
C70.6882 (3)0.3422 (2)0.31032 (18)0.0487 (6)
C80.7672 (3)0.2741 (3)0.3592 (2)0.0679 (9)
H8A0.71040.19220.34560.102*
H8B0.79740.30940.42240.102*
H8C0.84440.27710.34100.102*
C90.5518 (2)0.3174 (2)0.28333 (17)0.0420 (6)
C100.4863 (2)0.4002 (2)0.24045 (16)0.0399 (5)
H10A0.40330.35080.19060.048*
C110.4469 (2)0.4729 (2)0.30959 (15)0.0367 (5)
C120.3119 (2)0.4478 (2)0.30282 (17)0.0407 (6)
H12A0.24290.39200.25340.049*
C130.2829 (3)0.5081 (2)0.37171 (18)0.0462 (6)
C140.3790 (3)0.5935 (2)0.44488 (19)0.0519 (7)
H14A0.35490.63220.48950.062*
C150.5130 (3)0.6205 (2)0.45048 (18)0.0509 (6)
H15A0.58090.67930.49870.061*
C160.5456 (3)0.5593 (2)0.38350 (17)0.0445 (6)
H16A0.63620.57690.38840.053*
C170.4665 (3)0.2170 (2)0.30386 (18)0.0466 (6)
C180.2275 (3)0.1374 (2)0.27749 (18)0.0459 (6)
C190.1148 (2)0.0392 (2)0.21225 (16)0.0399 (6)
C200.0079 (3)0.0098 (2)0.22210 (18)0.0484 (6)
C210.0416 (3)0.0664 (3)0.2993 (2)0.0715 (9)
H21A0.00180.15170.31530.107*
H21B0.00990.03580.34940.107*
H21C0.13810.04790.28240.107*
C220.1134 (3)0.1310 (2)0.07489 (17)0.0454 (6)
C230.2531 (3)0.2037 (3)0.0100 (2)0.0646 (8)
H23A0.24730.26640.03260.097*
H23B0.29200.15290.02070.097*
H23C0.30930.23840.04180.097*
C240.0062 (3)0.1113 (2)0.06206 (16)0.0423 (6)
C250.0137 (3)0.1674 (2)0.02374 (18)0.0510 (6)
C260.1673 (4)0.2005 (4)0.0973 (2)0.0832 (11)
H26A0.13140.17200.14860.100*
H26B0.12220.28630.11200.100*
C270.3136 (5)0.1735 (5)0.0755 (3)0.1079 (15)
H27A0.33170.20680.12720.162*
H27B0.34700.20780.02800.162*
H27C0.35810.08830.05690.162*
C280.1392 (2)0.0350 (2)0.13605 (16)0.0389 (5)
H28A0.19300.02010.11100.047*
C290.2221 (2)0.1100 (2)0.17451 (15)0.0386 (5)
C300.3545 (3)0.0891 (2)0.17608 (17)0.0462 (6)
H30A0.39320.03220.14990.055*
C310.4280 (3)0.1543 (3)0.2171 (2)0.0553 (7)
C320.3777 (4)0.2385 (3)0.2573 (2)0.0687 (9)
H32A0.43060.27930.28590.082*
C330.2447 (4)0.2606 (3)0.2539 (3)0.0746 (10)
H33A0.20620.31900.27900.090*
C340.1692 (3)0.1971 (3)0.2137 (2)0.0576 (7)
H34A0.08030.21290.21260.069*
C350.0780 (5)0.7699 (6)0.4520 (4)0.147 (2)
H35A0.10230.83980.46640.220*
H35B0.07100.73220.50020.220*
H35C0.14640.71490.39850.220*
C360.0499 (6)0.8038 (5)0.4382 (3)0.1156 (16)
C370.2697 (6)0.9385 (6)0.4697 (5)0.148 (2)
H37A0.30880.87540.47510.177*
H37B0.25690.94940.41000.177*
C380.3552 (7)1.0415 (6)0.5308 (6)0.179 (3)
H38A0.44001.06430.52050.268*
H38B0.37051.02960.58970.268*
H38C0.31581.10360.52580.268*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
O10.0542 (12)0.0670 (13)0.0531 (11)0.0188 (10)0.0143 (10)0.0219 (10)
O20.0763 (17)0.119 (2)0.0955 (18)0.0094 (16)0.0328 (16)0.0624 (17)
O30.092 (2)0.170 (3)0.148 (3)0.011 (2)0.085 (2)0.022 (2)
O40.0395 (13)0.135 (2)0.101 (2)0.0202 (15)0.0219 (15)0.0007 (18)
O50.0540 (13)0.0688 (14)0.0823 (15)0.0167 (11)0.0092 (12)0.0341 (12)
O60.0352 (10)0.0439 (10)0.0494 (10)0.0007 (8)0.0077 (8)0.0057 (8)
O70.0579 (13)0.0689 (13)0.0547 (12)0.0055 (10)0.0163 (11)0.0115 (10)
O80.0691 (18)0.144 (3)0.141 (3)0.067 (2)0.0239 (18)0.039 (2)
O90.0567 (16)0.151 (3)0.157 (3)0.0430 (18)0.057 (2)0.068 (2)
O100.0725 (16)0.0886 (16)0.0471 (12)0.0048 (13)0.0071 (12)0.0043 (12)
O110.0645 (13)0.0777 (14)0.0449 (11)0.0223 (11)0.0232 (10)0.0048 (10)
O120.165 (4)0.187 (4)0.163 (4)0.025 (3)0.074 (4)0.023 (3)
O130.097 (3)0.110 (3)0.173 (4)0.009 (2)0.029 (3)0.002 (3)
N10.0251 (11)0.0760 (16)0.0660 (15)0.0077 (11)0.0129 (11)0.0130 (13)
N20.0517 (17)0.0704 (17)0.093 (2)0.0197 (14)0.0391 (18)0.0094 (15)
N30.0325 (12)0.0622 (14)0.0568 (14)0.0059 (11)0.0161 (11)0.0063 (11)
N40.0482 (16)0.091 (2)0.089 (2)0.0331 (16)0.0164 (16)0.0106 (17)
C10.081 (3)0.128 (4)0.093 (3)0.050 (3)0.020 (2)0.048 (3)
C20.081 (2)0.077 (2)0.0582 (19)0.0296 (19)0.0132 (18)0.0244 (16)
C30.0543 (18)0.0628 (18)0.0519 (16)0.0078 (15)0.0211 (15)0.0132 (14)
C40.0403 (14)0.0511 (15)0.0458 (14)0.0066 (12)0.0172 (13)0.0048 (12)
C50.0398 (15)0.0605 (17)0.0502 (16)0.0044 (13)0.0177 (14)0.0037 (13)
C60.0493 (19)0.104 (3)0.069 (2)0.0057 (18)0.0285 (18)0.0182 (19)
C70.0378 (14)0.0526 (15)0.0528 (15)0.0158 (12)0.0166 (13)0.0034 (12)
C80.0488 (17)0.078 (2)0.082 (2)0.0343 (17)0.0186 (17)0.0196 (18)
C90.0320 (12)0.0417 (13)0.0445 (13)0.0097 (11)0.0108 (11)0.0004 (10)
C100.0282 (12)0.0410 (13)0.0408 (13)0.0043 (10)0.0083 (11)0.0039 (10)
C110.0321 (12)0.0369 (12)0.0397 (12)0.0103 (10)0.0107 (11)0.0112 (10)
C120.0310 (12)0.0372 (13)0.0486 (14)0.0081 (10)0.0101 (11)0.0093 (11)
C130.0411 (14)0.0468 (14)0.0598 (16)0.0192 (12)0.0235 (14)0.0195 (12)
C140.0594 (18)0.0481 (15)0.0521 (16)0.0216 (14)0.0236 (15)0.0093 (12)
C150.0501 (16)0.0476 (15)0.0448 (14)0.0136 (13)0.0082 (13)0.0045 (12)
C160.0344 (13)0.0463 (14)0.0488 (14)0.0121 (11)0.0116 (12)0.0094 (11)
C170.0406 (14)0.0433 (14)0.0465 (15)0.0127 (12)0.0074 (13)0.0027 (12)
C180.0424 (14)0.0423 (14)0.0497 (15)0.0129 (12)0.0161 (13)0.0053 (12)
C190.0393 (13)0.0355 (12)0.0429 (13)0.0106 (11)0.0142 (12)0.0083 (10)
C200.0395 (14)0.0525 (15)0.0508 (15)0.0149 (12)0.0159 (13)0.0071 (12)
C210.0560 (19)0.085 (2)0.069 (2)0.0208 (17)0.0313 (17)0.0036 (17)
C220.0392 (14)0.0384 (13)0.0482 (14)0.0034 (11)0.0091 (12)0.0104 (11)
C230.0443 (17)0.0677 (19)0.0605 (18)0.0014 (14)0.0055 (15)0.0124 (15)
C240.0419 (14)0.0373 (13)0.0425 (13)0.0083 (11)0.0111 (12)0.0116 (10)
C250.0573 (18)0.0441 (15)0.0415 (15)0.0096 (13)0.0107 (14)0.0084 (12)
C260.108 (3)0.104 (3)0.0523 (19)0.050 (2)0.041 (2)0.0108 (18)
C270.127 (4)0.139 (4)0.091 (3)0.068 (3)0.069 (3)0.024 (3)
C280.0337 (13)0.0369 (13)0.0415 (13)0.0056 (10)0.0138 (11)0.0068 (10)
C290.0383 (13)0.0369 (13)0.0398 (13)0.0098 (11)0.0164 (11)0.0075 (10)
C300.0399 (14)0.0468 (14)0.0491 (15)0.0121 (12)0.0167 (13)0.0072 (11)
C310.0419 (15)0.0573 (17)0.0642 (18)0.0215 (14)0.0159 (15)0.0056 (14)
C320.074 (2)0.072 (2)0.073 (2)0.0427 (19)0.0213 (19)0.0281 (17)
C330.079 (2)0.079 (2)0.097 (3)0.041 (2)0.046 (2)0.052 (2)
C340.0554 (17)0.0609 (18)0.0729 (19)0.0244 (15)0.0344 (17)0.0308 (15)
C350.088 (4)0.177 (6)0.123 (4)0.003 (4)0.041 (3)0.023 (4)
C360.102 (4)0.121 (4)0.079 (3)0.000 (3)0.015 (3)0.000 (3)
C370.112 (5)0.128 (5)0.154 (5)0.001 (4)0.032 (4)0.004 (4)
C380.140 (6)0.144 (6)0.204 (7)0.023 (5)0.039 (6)0.002 (5)
Geometric parameters (Å, º) top
O1—C21.453 (4)C12—H12A0.9300
O1—C31.345 (4)C13—C141.367 (4)
O2—C31.212 (3)C14—C151.379 (4)
O3—N21.218 (4)C14—H14A0.9300
O4—N21.192 (4)C15—C161.389 (3)
O5—C171.199 (3)C15—H15A0.9300
O6—C171.391 (3)C16—H16A0.9300
O6—C181.399 (3)C18—C191.445 (4)
O7—C181.203 (3)C19—C201.350 (3)
O8—N41.211 (4)C19—C281.526 (3)
O9—N41.217 (4)C20—C211.504 (4)
O10—C251.204 (4)C21—H21A0.9600
O11—C251.347 (3)C21—H21B0.9600
O11—C261.451 (3)C21—H21C0.9600
O12—C361.269 (6)C22—C241.341 (3)
O13—C361.256 (6)C22—C231.504 (4)
O13—C371.482 (6)C23—H23A0.9600
N1—C71.370 (3)C23—H23B0.9600
N1—C51.381 (4)C23—H23C0.9600
N1—H1D0.8600C24—C251.472 (3)
N2—C131.471 (4)C24—C281.521 (4)
N3—C201.369 (4)C26—C271.462 (6)
N3—C221.385 (3)C26—H26A0.9700
N3—H3A0.8600C26—H26B0.9700
N4—C311.469 (4)C27—H27A0.9600
C1—C21.485 (5)C27—H27B0.9600
C1—H1A0.9600C27—H27C0.9600
C1—H1B0.9600C28—C291.526 (3)
C1—H1C0.9600C28—H28A0.9800
C2—H2A0.9700C29—C301.388 (3)
C2—H2B0.9700C29—C341.388 (4)
C3—C41.461 (4)C30—C311.381 (4)
C4—C51.347 (4)C30—H30A0.9300
C4—C101.528 (3)C31—C321.366 (4)
C5—C61.512 (4)C32—C331.383 (5)
C6—H6A0.9600C32—H32A0.9300
C6—H6B0.9600C33—C341.374 (4)
C6—H6C0.9600C33—H33A0.9300
C7—C91.356 (4)C34—H34A0.9300
C7—C81.501 (4)C35—C361.434 (7)
C8—H8A0.9600C35—H35A0.9600
C8—H8B0.9600C35—H35B0.9600
C8—H8C0.9600C35—H35C0.9600
C9—C171.459 (4)C37—C381.352 (8)
C9—C101.522 (4)C37—H37A0.9700
C10—C111.531 (3)C37—H37B0.9700
C10—H10A0.9800C38—H38A0.9600
C11—C121.387 (3)C38—H38B0.9600
C11—C161.387 (4)C38—H38C0.9600
C12—C131.385 (3)
C3—O1—C2115.9 (2)C20—C19—C18120.0 (2)
C17—O6—C18118.9 (2)C20—C19—C28120.8 (2)
C25—O11—C26116.9 (3)C18—C19—C28119.0 (2)
C36—O13—C37118.7 (5)C19—C20—N3119.6 (2)
C7—N1—C5123.9 (2)C19—C20—C21126.2 (3)
C7—N1—H1D118.1N3—C20—C21114.2 (2)
C5—N1—H1D118.1C20—C21—H21A109.5
O4—N2—O3122.1 (3)C20—C21—H21B109.5
O4—N2—C13119.9 (2)H21A—C21—H21B109.5
O3—N2—C13118.0 (3)C20—C21—H21C109.5
C20—N3—C22124.1 (2)H21A—C21—H21C109.5
C20—N3—H3A118.0H21B—C21—H21C109.5
C22—N3—H3A118.0C24—C22—N3119.1 (2)
O8—N4—O9122.1 (3)C24—C22—C23128.7 (2)
O8—N4—C31119.7 (3)N3—C22—C23112.1 (2)
O9—N4—C31118.1 (3)C22—C23—H23A109.5
C2—C1—H1A109.5C22—C23—H23B109.5
C2—C1—H1B109.5H23A—C23—H23B109.5
H1A—C1—H1B109.5C22—C23—H23C109.5
C2—C1—H1C109.5H23A—C23—H23C109.5
H1A—C1—H1C109.5H23B—C23—H23C109.5
H1B—C1—H1C109.5C22—C24—C25120.8 (2)
O1—C2—C1107.5 (3)C22—C24—C28121.7 (2)
O1—C2—H2A110.2C25—C24—C28117.4 (2)
C1—C2—H2A110.2O10—C25—O11121.5 (2)
O1—C2—H2B110.2O10—C25—C24127.6 (3)
C1—C2—H2B110.2O11—C25—C24110.9 (2)
H2A—C2—H2B108.5O11—C26—C27108.3 (3)
O2—C3—O1121.1 (3)O11—C26—H26A110.0
O2—C3—C4127.0 (3)C27—C26—H26A110.0
O1—C3—C4111.9 (2)O11—C26—H26B110.0
C5—C4—C3120.9 (2)C27—C26—H26B110.0
C5—C4—C10121.1 (3)H26A—C26—H26B108.4
C3—C4—C10117.9 (2)C26—C27—H27A109.5
C4—C5—N1119.6 (2)C26—C27—H27B109.5
C4—C5—C6127.8 (3)H27A—C27—H27B109.5
N1—C5—C6112.6 (3)C26—C27—H27C109.5
C5—C6—H6A109.5H27A—C27—H27C109.5
C5—C6—H6B109.5H27B—C27—H27C109.5
H6A—C6—H6B109.5C24—C28—C29112.43 (19)
C5—C6—H6C109.5C24—C28—C19111.33 (19)
H6A—C6—H6C109.5C29—C28—C19108.39 (19)
H6B—C6—H6C109.5C24—C28—H28A108.2
C9—C7—N1119.3 (3)C29—C28—H28A108.2
C9—C7—C8127.0 (3)C19—C28—H28A108.2
N1—C7—C8113.7 (2)C30—C29—C34118.0 (2)
C7—C8—H8A109.5C30—C29—C28121.4 (2)
C7—C8—H8B109.5C34—C29—C28120.5 (2)
H8A—C8—H8B109.5C31—C30—C29118.9 (2)
C7—C8—H8C109.5C31—C30—H30A120.5
H8A—C8—H8C109.5C29—C30—H30A120.5
H8B—C8—H8C109.5C32—C31—C30123.4 (3)
C7—C9—C17120.0 (2)C32—C31—N4118.4 (3)
C7—C9—C10121.2 (2)C30—C31—N4118.2 (3)
C17—C9—C10118.4 (2)C31—C32—C33117.3 (3)
C9—C10—C4110.9 (2)C31—C32—H32A121.3
C9—C10—C11108.56 (19)C33—C32—H32A121.3
C4—C10—C11112.24 (19)C34—C33—C32120.6 (3)
C9—C10—H10A108.4C34—C33—H33A119.7
C4—C10—H10A108.4C32—C33—H33A119.7
C11—C10—H10A108.4C33—C34—C29121.7 (3)
C12—C11—C16118.5 (2)C33—C34—H34A119.2
C12—C11—C10120.5 (2)C29—C34—H34A119.2
C16—C11—C10120.8 (2)C36—C35—H35A109.5
C13—C12—C11118.1 (2)C36—C35—H35B109.5
C13—C12—H12A120.9H35A—C35—H35B109.5
C11—C12—H12A120.9C36—C35—H35C109.5
C14—C13—C12123.9 (2)H35A—C35—H35C109.5
C14—C13—N2118.6 (2)H35B—C35—H35C109.5
C12—C13—N2117.5 (3)O13—C36—O12119.0 (5)
C13—C14—C15117.9 (2)O13—C36—C35118.6 (5)
C13—C14—H14A121.1O12—C36—C35121.0 (5)
C15—C14—H14A121.1C38—C37—O13110.1 (6)
C14—C15—C16119.5 (3)C38—C37—H37A109.6
C14—C15—H15A120.2O13—C37—H37A109.6
C16—C15—H15A120.2C38—C37—H37B109.6
C11—C16—C15122.0 (2)O13—C37—H37B109.6
C11—C16—H16A119.0H37A—C37—H37B108.1
C15—C16—H16A119.0C37—C38—H38A109.5
O5—C17—O6120.2 (2)C37—C38—H38B109.5
O5—C17—C9128.3 (3)H38A—C38—H38B109.5
O6—C17—C9111.5 (2)C37—C38—H38C109.5
O7—C18—O6119.0 (2)H38A—C38—H38C109.5
O7—C18—C19128.9 (2)H38B—C38—H38C109.5
O6—C18—C19111.99 (19)
C3—O1—C2—C1177.8 (3)O7—C18—C19—C2013.7 (4)
C2—O1—C3—O23.2 (4)O6—C18—C19—C20163.1 (2)
C2—O1—C3—C4177.2 (2)O7—C18—C19—C28162.4 (3)
O2—C3—C4—C50.5 (5)O6—C18—C19—C2820.8 (3)
O1—C3—C4—C5179.9 (2)C18—C19—C20—N3175.8 (2)
O2—C3—C4—C10177.5 (3)C28—C19—C20—N38.1 (4)
O1—C3—C4—C102.1 (3)C18—C19—C20—C213.2 (4)
C3—C4—C5—N1176.5 (2)C28—C19—C20—C21172.8 (3)
C10—C4—C5—N15.5 (4)C22—N3—C20—C198.4 (4)
C3—C4—C5—C62.8 (4)C22—N3—C20—C21170.8 (3)
C10—C4—C5—C6175.1 (3)C20—N3—C22—C2411.9 (4)
C7—N1—C5—C410.9 (4)C20—N3—C22—C23167.1 (3)
C7—N1—C5—C6168.6 (3)N3—C22—C24—C25178.9 (2)
C5—N1—C7—C910.2 (4)C23—C22—C24—C252.3 (4)
C5—N1—C7—C8168.0 (2)N3—C22—C24—C281.5 (4)
N1—C7—C9—C17179.9 (2)C23—C22—C24—C28179.7 (3)
C8—C7—C9—C171.9 (4)C26—O11—C25—O105.1 (4)
N1—C7—C9—C106.8 (4)C26—O11—C25—C24174.0 (2)
C8—C7—C9—C10175.2 (2)C22—C24—C25—O102.6 (4)
C7—C9—C10—C420.2 (3)C28—C24—C25—O10179.9 (3)
C17—C9—C10—C4166.4 (2)C22—C24—C25—O11176.4 (2)
C7—C9—C10—C11103.6 (3)C28—C24—C25—O111.1 (3)
C17—C9—C10—C1169.8 (3)C25—O11—C26—C27172.2 (3)
C5—C4—C10—C919.5 (3)C22—C24—C28—C29106.4 (3)
C3—C4—C10—C9162.5 (2)C25—C24—C28—C2971.1 (3)
C5—C4—C10—C11102.1 (3)C22—C24—C28—C1915.4 (3)
C3—C4—C10—C1175.9 (3)C25—C24—C28—C19167.1 (2)
C9—C10—C11—C12106.8 (3)C20—C19—C28—C2418.8 (3)
C4—C10—C11—C12130.3 (2)C18—C19—C28—C24165.2 (2)
C9—C10—C11—C1668.7 (3)C20—C19—C28—C29105.4 (3)
C4—C10—C11—C1654.2 (3)C18—C19—C28—C2970.7 (3)
C16—C11—C12—C131.9 (3)C24—C28—C29—C30123.8 (2)
C10—C11—C12—C13173.7 (2)C19—C28—C29—C30112.7 (2)
C11—C12—C13—C142.0 (4)C24—C28—C29—C3459.8 (3)
C11—C12—C13—N2177.0 (2)C19—C28—C29—C3463.7 (3)
O4—N2—C13—C14160.6 (3)C34—C29—C30—C310.8 (4)
O3—N2—C13—C1422.1 (4)C28—C29—C30—C31175.6 (2)
O4—N2—C13—C1220.4 (4)C29—C30—C31—C320.5 (4)
O3—N2—C13—C12156.9 (3)C29—C30—C31—N4179.6 (2)
C12—C13—C14—C150.4 (4)O8—N4—C31—C327.4 (5)
N2—C13—C14—C15178.5 (2)O9—N4—C31—C32169.9 (3)
C13—C14—C15—C161.2 (4)O8—N4—C31—C30172.5 (3)
C12—C11—C16—C150.3 (4)O9—N4—C31—C3010.2 (4)
C10—C11—C16—C15175.3 (2)C30—C31—C32—C331.8 (5)
C14—C15—C16—C111.3 (4)N4—C31—C32—C33178.3 (3)
C18—O6—C17—O538.3 (3)C31—C32—C33—C341.9 (5)
C18—O6—C17—C9143.5 (2)C32—C33—C34—C290.7 (5)
C7—C9—C17—O520.9 (4)C30—C29—C34—C330.7 (4)
C10—C9—C17—O5152.6 (3)C28—C29—C34—C33175.8 (3)
C7—C9—C17—O6157.1 (2)C37—O13—C36—O1212.6 (9)
C10—C9—C17—O629.4 (3)C37—O13—C36—C35179.6 (5)
C17—O6—C18—O737.7 (3)C36—O13—C37—C38172.8 (6)
C17—O6—C18—C19145.1 (2)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N1—H1D···O4i0.862.393.121 (4)143
N3—H3A···O9ii0.862.373.131 (4)147
C6—H6C···O12i0.962.363.317 (6)178
C23—H23C···O2iii0.962.443.348 (5)157
Symmetry codes: (i) x+1, y, z; (ii) x1, y, z; (iii) x1, y1, z.

Experimental details

Crystal data
Chemical formulaC34H34N4O11·C4H8O2
Mr762.76
Crystal system, space groupTriclinic, P1
Temperature (K)293
a, b, c (Å)10.896 (2), 12.017 (2), 16.162 (3)
α, β, γ (°)99.59 (3), 106.29 (3), 105.69 (3)
V3)1887.1 (9)
Z2
Radiation typeMo Kα
µ (mm1)0.10
Crystal size (mm)0.28 × 0.22 × 0.10
Data collection
DiffractometerRigaku R-AXIS RAPID
diffractometer
Absorption correction
No. of measured, independent and
observed [I > 2σ(I)] reflections
18422, 6953, 4362
Rint0.038
(sin θ/λ)max1)0.606
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.065, 0.206, 1.08
No. of reflections6953
No. of parameters504
H-atom treatmentH-atom parameters constrained
Δρmax, Δρmin (e Å3)0.57, 0.45

Computer programs: PROCESS-AUTO (Rigaku, 1998), PROCESS-AUTO, CrystalStructure (Rigaku/MSC, 2002), SHELXS97 (Sheldrick, 1997), SHELXL97 (Sheldrick, 1997), SHELXTL (Bruker, 2002), SHELXTL.

Selected bond lengths (Å) top
O1—C21.453 (4)O10—C251.204 (4)
O1—C31.345 (4)O11—C251.347 (3)
O2—C31.212 (3)O11—C261.451 (3)
O5—C171.199 (3)O12—C361.269 (6)
O6—C171.391 (3)O13—C361.256 (6)
O6—C181.399 (3)O13—C371.482 (6)
O7—C181.203 (3)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N1—H1D···O4i0.862.393.121 (4)143
N3—H3A···O9ii0.862.373.131 (4)147
C6—H6C···O12i0.962.363.317 (6)178
C23—H23C···O2iii0.962.443.348 (5)157
Symmetry codes: (i) x+1, y, z; (ii) x1, y, z; (iii) x1, y1, z.
 

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