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The title compound, C20H19NO7, crystallizes in the space group Pna21. X-ray analysis shows the compound has the desired 3'-hydroxy and 4'-methoxy substitution pattern, as in the natural template combretastatin A-4.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536805003685/lh6360sup1.cif
Contains datablocks I, global

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536805003685/lh6360Isup2.hkl
Contains datablock I

CCDC reference: 269813

Key indicators

  • Single-crystal X-ray study
  • T = 295 K
  • Mean [sigma](C-C) = 0.005 Å
  • R factor = 0.051
  • wR factor = 0.145
  • Data-to-parameter ratio = 7.4

checkCIF/PLATON results

No syntax errors found



Alert level A PLAT222_ALERT_3_A Large Non-Solvent H Ueq(max)/Ueq(min) ... 6.73 Ratio
Alert level C RINTA01_ALERT_3_C The value of Rint is greater than 0.10 Rint given 0.135 PLAT020_ALERT_3_C The value of Rint is greater than 0.10 ......... 0.14 PLAT089_ALERT_3_C Poor Data / Parameter Ratio (Zmax .LT. 18) ..... 7.36 PLAT220_ALERT_2_C Large Non-Solvent C Ueq(max)/Ueq(min) ... 3.00 Ratio PLAT340_ALERT_3_C Low Bond Precision on C-C bonds (x 1000) Ang ... 5
Alert level G REFLT03_ALERT_4_G Please check that the estimate of the number of Friedel pairs is correct. If it is not, please give the correct count in the _publ_section_exptl_refinement section of the submitted CIF. From the CIF: _diffrn_reflns_theta_max 74.01 From the CIF: _reflns_number_total 1972 Count of symmetry unique reflns 1975 Completeness (_total/calc) 99.85% TEST3: Check Friedels for noncentro structure Estimate of Friedel pairs measured 0 Fraction of Friedel pairs measured 0.000 Are heavy atom types Z>Si present no
1 ALERT level A = In general: serious problem 0 ALERT level B = Potentially serious problem 5 ALERT level C = Check and explain 1 ALERT level G = General alerts; check 0 ALERT type 1 CIF construction/syntax error, inconsistent or missing data 1 ALERT type 2 Indicator that the structure model may be wrong or deficient 5 ALERT type 3 Indicator that the structure quality may be low 1 ALERT type 4 Improvement, methodology, query or suggestion

Computing details top

Data collection: CAD-4 Software (Enraf–Nonius, 1998); cell refinement: CAD-4 Software; data reduction: CORINC (Dräger & Gattow, 1971); program(s) used to solve structure: SIR92 (Altomare et al., 1994); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEPII (Johnson, 1976); software used to prepare material for publication: SHELXL97.

4-(3-hydroxy-4-methoxyphenyl)-3-(3,4,5-trimethoxyphenyl)-2,5-dihydro- 1H-pyrrole-2,5-dione top
Crystal data top
C20H19NO7Dx = 1.424 Mg m3
Mr = 385.22Melting point: 234 K
Orthorhombic, Pna21Cu Kα radiation, λ = 1.54178 Å
Hall symbol: P 2c -2nCell parameters from 25 reflections
a = 14.0827 (17) Åθ = 21–28°
b = 17.674 (3) ŵ = 0.92 mm1
c = 7.2238 (4) ÅT = 295 K
V = 1798.0 (4) Å3Needle, green yellow
Z = 40.58 × 0.12 × 0.04 mm
F(000) = 808
Data collection top
Enraf–Nonius CAD-4
diffractometer
1654 reflections with I > 2σ(I)
Radiation source: rotating anodeRint = 0.135
Graphite monochromatorθmax = 74.0°
θ/2ω scansh = 1717
Absorption correction: numerical
(de Meulenaer & Tompa, 1965)
k = 2221
Tmin = 0.69, Tmax = 0.965l = 88
3459 measured reflections3 standard reflections every 60 min
1972 independent reflections intensity decay: 3%
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)] = 0.051Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.145Only H-atom displacement parameters refined
S = 1.07 w = 1/[σ2(Fo2) + (0.0712P)2]
where P = (Fo2 + 2Fc2)/3
1972 reflections(Δ/σ)max < 0.001
268 parametersΔρmax = 0.44 e Å3
1 restraintΔρmin = 0.23 e Å3
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
C10.1848 (2)0.02928 (17)0.5300 (6)0.0277 (7)
C20.0906 (2)0.02839 (17)0.5627 (5)0.0261 (7)
C30.0601 (3)0.10821 (18)0.6082 (6)0.0286 (8)
C50.2188 (3)0.10917 (19)0.5518 (7)0.0324 (8)
N40.1406 (2)0.15187 (15)0.5968 (6)0.0332 (8)
H40.14710.19500.61930.031 (12)*
C60.2515 (2)0.03134 (18)0.4829 (6)0.0275 (8)
C70.2352 (3)0.07935 (18)0.3325 (6)0.0323 (8)
H70.18050.07420.26160.017 (9)*
C80.3018 (3)0.13503 (19)0.2897 (6)0.0320 (8)
C90.3825 (3)0.14408 (19)0.3977 (6)0.0309 (8)
C100.3980 (3)0.0965 (2)0.5472 (7)0.0374 (9)
C110.3332 (3)0.0390 (2)0.5867 (7)0.0353 (9)
H110.34510.00570.68360.061 (16)*
C120.0225 (2)0.03464 (17)0.5744 (6)0.0260 (7)
C130.0731 (3)0.0237 (2)0.5296 (6)0.0323 (8)
H130.09350.02320.48670.050 (14)*
C140.1375 (3)0.0822 (2)0.5486 (7)0.0366 (9)
H140.20080.07460.51710.021 (9)*
C150.1082 (3)0.1526 (2)0.6148 (7)0.0356 (9)
C160.0121 (3)0.16363 (18)0.6583 (6)0.0337 (8)
C170.0519 (3)0.10542 (19)0.6374 (6)0.0313 (8)
H170.11560.11340.66550.015 (8)*
O180.01722 (18)0.13021 (14)0.6544 (6)0.0396 (7)
O190.29849 (19)0.13220 (15)0.5328 (7)0.0507 (10)
O200.2942 (2)0.18510 (16)0.1466 (5)0.0492 (9)
C210.2285 (4)0.1705 (3)0.0040 (8)0.0559 (14)
H21A0.16510.17360.05250.093 (14)*
H21B0.23920.12070.04490.093 (14)*
H21C0.23620.20720.09270.093 (14)*
O220.4435 (2)0.20294 (14)0.3608 (5)0.0406 (7)
C230.5255 (3)0.1831 (3)0.2582 (12)0.0630 (17)
H23A0.50700.16490.13830.101 (15)*
H23B0.55980.14420.32250.101 (15)*
H23C0.56540.22680.24400.101 (15)*
O240.4781 (2)0.11165 (18)0.6479 (6)0.0576 (11)
C250.5024 (4)0.0617 (3)0.7931 (11)0.078 (2)
H25A0.51090.01170.74430.079 (12)*
H25B0.45250.06130.88370.079 (12)*
H25C0.56040.07830.85000.079 (12)*
O260.1656 (2)0.21367 (16)0.6431 (5)0.0459 (8)
C270.2594 (3)0.2101 (3)0.5727 (10)0.0545 (13)
H27A0.29730.17830.65120.069 (10)*
H27B0.25820.18940.44980.069 (10)*
H27C0.28610.26000.56940.069 (10)*
O280.0205 (2)0.23070 (15)0.7287 (6)0.0528 (10)
H280.01250.27020.67820.050 (14)*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
C10.0364 (18)0.0220 (14)0.0246 (19)0.0007 (12)0.0037 (17)0.0014 (14)
C20.0297 (17)0.0267 (15)0.0219 (19)0.0020 (12)0.0001 (15)0.0011 (14)
C30.0354 (17)0.0276 (15)0.0229 (19)0.0027 (13)0.0003 (15)0.0002 (13)
C50.038 (2)0.0287 (16)0.031 (2)0.0013 (14)0.0018 (19)0.0017 (15)
N40.0385 (17)0.0200 (13)0.041 (2)0.0008 (11)0.0023 (16)0.0031 (12)
C60.0277 (17)0.0266 (15)0.028 (2)0.0014 (13)0.0017 (15)0.0014 (14)
C70.0329 (18)0.0330 (17)0.031 (2)0.0043 (14)0.0081 (17)0.0056 (16)
C80.0383 (19)0.0295 (16)0.028 (2)0.0049 (14)0.0013 (18)0.0027 (15)
C90.0335 (18)0.0251 (15)0.034 (2)0.0059 (13)0.0002 (17)0.0020 (14)
C100.0350 (18)0.0359 (18)0.041 (3)0.0058 (15)0.011 (2)0.0017 (18)
C110.0362 (19)0.0349 (17)0.035 (2)0.0028 (14)0.0078 (18)0.0088 (15)
C120.0299 (17)0.0251 (15)0.0231 (19)0.0005 (12)0.0010 (15)0.0037 (13)
C130.0367 (19)0.0343 (17)0.026 (2)0.0025 (14)0.0000 (18)0.0011 (14)
C140.0301 (17)0.047 (2)0.033 (2)0.0018 (15)0.0003 (18)0.0020 (19)
C150.045 (2)0.0355 (18)0.026 (2)0.0094 (15)0.0057 (18)0.0058 (15)
C160.048 (2)0.0263 (15)0.027 (2)0.0003 (14)0.0018 (19)0.0005 (16)
C170.0334 (17)0.0288 (15)0.032 (2)0.0005 (13)0.0070 (17)0.0064 (15)
O180.0328 (13)0.0345 (12)0.052 (2)0.0076 (10)0.0012 (15)0.0047 (13)
O190.0332 (14)0.0375 (14)0.081 (3)0.0071 (11)0.0056 (19)0.0067 (17)
O200.0585 (18)0.0453 (14)0.044 (2)0.0226 (13)0.0192 (18)0.0207 (15)
C210.065 (3)0.065 (3)0.038 (3)0.023 (2)0.019 (3)0.022 (2)
O220.0372 (14)0.0333 (13)0.051 (2)0.0125 (11)0.0045 (15)0.0029 (13)
C230.045 (2)0.054 (3)0.090 (5)0.004 (2)0.019 (3)0.011 (3)
O240.0544 (19)0.0536 (16)0.065 (3)0.0221 (14)0.032 (2)0.0185 (19)
C250.074 (4)0.077 (3)0.084 (6)0.025 (3)0.054 (4)0.023 (4)
O260.0435 (16)0.0487 (15)0.046 (2)0.0147 (12)0.0006 (17)0.0030 (15)
C270.044 (2)0.063 (3)0.057 (4)0.019 (2)0.002 (3)0.002 (3)
O280.064 (2)0.0324 (14)0.062 (3)0.0063 (13)0.017 (2)0.0070 (14)
Geometric parameters (Å, º) top
C1—C21.347 (5)C14—C151.395 (6)
C1—C61.466 (5)C14—H140.9300
C1—C51.500 (4)C15—O261.363 (4)
C2—C121.472 (4)C15—C161.404 (6)
C2—C31.511 (4)C16—O281.369 (4)
C3—O181.203 (5)C16—C171.376 (5)
C3—N41.374 (5)C17—H170.9300
C5—O191.201 (4)O20—C211.409 (6)
C5—N41.374 (5)C21—H21A0.9600
N4—H40.7842C21—H21B0.9600
C6—C111.380 (5)C21—H21C0.9600
C6—C71.398 (5)O22—C231.416 (6)
C7—C81.394 (5)C23—H23A0.9600
C7—H70.9300C23—H23B0.9600
C8—O201.365 (5)C23—H23C0.9600
C8—C91.387 (5)O24—C251.413 (7)
C9—O221.376 (4)C25—H25A0.9600
C9—C101.385 (6)C25—H25B0.9600
C10—O241.369 (5)C25—H25C0.9600
C10—C111.395 (5)O26—C271.417 (6)
C11—H110.9300C27—H27A0.9600
C12—C171.394 (5)C27—H27B0.9600
C12—C131.399 (5)C27—H27C0.9600
C13—C141.382 (5)O28—H280.9147
C13—H130.9300
C2—C1—C6131.6 (3)C13—C14—H14119.7
C2—C1—C5107.9 (3)C15—C14—H14119.7
C6—C1—C5120.5 (3)O26—C15—C14125.6 (4)
C1—C2—C12131.3 (3)O26—C15—C16115.4 (3)
C1—C2—C3107.9 (3)C14—C15—C16119.0 (3)
C12—C2—C3120.6 (3)O28—C16—C17117.9 (4)
O18—C3—N4125.6 (3)O28—C16—C15121.8 (3)
O18—C3—C2128.3 (3)C17—C16—C15120.2 (3)
N4—C3—C2106.1 (3)C16—C17—C12120.8 (3)
O19—C5—N4126.1 (3)C16—C17—H17119.6
O19—C5—C1127.3 (3)C12—C17—H17119.6
N4—C5—C1106.6 (3)C8—O20—C21119.1 (3)
C3—N4—C5111.5 (3)O20—C21—H21A109.5
C3—N4—H4129.0O20—C21—H21B109.5
C5—N4—H4119.2H21A—C21—H21B109.5
C11—C6—C7120.0 (3)O20—C21—H21C109.5
C11—C6—C1118.7 (3)H21A—C21—H21C109.5
C7—C6—C1121.2 (3)H21B—C21—H21C109.5
C8—C7—C6119.4 (4)C9—O22—C23115.1 (3)
C8—C7—H7120.3O22—C23—H23A109.5
C6—C7—H7120.3O22—C23—H23B109.5
O20—C8—C9114.5 (3)H23A—C23—H23B109.5
O20—C8—C7124.9 (4)O22—C23—H23C109.5
C9—C8—C7120.5 (4)H23A—C23—H23C109.5
O22—C9—C10120.7 (4)H23B—C23—H23C109.5
O22—C9—C8119.3 (4)C10—O24—C25118.2 (3)
C10—C9—C8119.8 (3)O24—C25—H25A109.5
O24—C10—C9115.2 (3)O24—C25—H25B109.5
O24—C10—C11124.9 (4)H25A—C25—H25B109.5
C9—C10—C11119.9 (4)O24—C25—H25C109.5
C6—C11—C10120.4 (4)H25A—C25—H25C109.5
C6—C11—H11119.8H25B—C25—H25C109.5
C10—C11—H11119.8C15—O26—C27117.6 (4)
C17—C12—C13119.0 (3)O26—C27—H27A109.5
C17—C12—C2120.3 (3)O26—C27—H27B109.5
C13—C12—C2120.6 (3)H27A—C27—H27B109.5
C14—C13—C12120.3 (3)O26—C27—H27C109.5
C14—C13—H13119.8H27A—C27—H27C109.5
C12—C13—H13119.8H27B—C27—H27C109.5
C13—C14—C15120.5 (4)C16—O28—H28110.1
C6—C1—C2—C124.5 (8)C8—C9—C10—C111.0 (6)
C5—C1—C2—C12174.7 (4)C7—C6—C11—C102.6 (6)
C6—C1—C2—C3179.0 (4)C1—C6—C11—C10179.4 (4)
C5—C1—C2—C30.3 (5)O24—C10—C11—C6176.1 (4)
C1—C2—C3—O18176.0 (4)C9—C10—C11—C62.9 (7)
C12—C2—C3—O180.8 (7)C1—C2—C12—C1730.7 (7)
C1—C2—C3—N40.6 (5)C3—C2—C12—C17143.2 (4)
C12—C2—C3—N4175.8 (3)C1—C2—C12—C13151.8 (4)
C2—C1—C5—O19179.7 (5)C3—C2—C12—C1334.4 (6)
C6—C1—C5—O191.0 (7)C17—C12—C13—C140.4 (6)
C2—C1—C5—N40.2 (5)C2—C12—C13—C14177.2 (4)
C6—C1—C5—N4179.5 (4)C12—C13—C14—C150.7 (7)
O18—C3—N4—C5176.0 (5)C13—C14—C15—O26178.4 (4)
C2—C3—N4—C50.7 (5)C13—C14—C15—C161.2 (7)
O19—C5—N4—C3179.9 (5)O26—C15—C16—O281.6 (6)
C1—C5—N4—C30.6 (5)C14—C15—C16—O28178.1 (5)
C2—C1—C6—C11128.1 (5)O26—C15—C16—C17179.1 (4)
C5—C1—C6—C1151.1 (5)C14—C15—C16—C170.6 (7)
C2—C1—C6—C753.9 (6)O28—C16—C17—C12177.1 (4)
C5—C1—C6—C7126.9 (4)C15—C16—C17—C120.6 (7)
C11—C6—C7—C80.4 (6)C13—C12—C17—C161.1 (6)
C1—C6—C7—C8178.4 (4)C2—C12—C17—C16176.5 (4)
C6—C7—C8—O20179.8 (4)C9—C8—O20—C21165.2 (4)
C6—C7—C8—C91.5 (6)C7—C8—O20—C2116.1 (7)
O20—C8—C9—O223.5 (6)C10—C9—O22—C2383.5 (6)
C7—C8—C9—O22175.3 (4)C8—C9—O22—C23100.0 (5)
O20—C8—C9—C10180.0 (4)C9—C10—O24—C25175.0 (5)
C7—C8—C9—C101.2 (6)C11—C10—O24—C256.0 (8)
O22—C9—C10—O241.6 (6)C14—C15—O26—C2710.8 (7)
C8—C9—C10—O24178.1 (4)C16—C15—O26—C27169.6 (4)
O22—C9—C10—C11177.4 (4)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N4—H4···O20i0.782.283.045 (4)164
O28—H28···O24ii0.912.102.909 (4)146
O28—H28···O22ii0.912.423.101 (5)131
Symmetry codes: (i) x+1/2, y1/2, z+1/2; (ii) x1/2, y+1/2, z.
 

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