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The title compound, C24H26N2O8, is a derivative of neihumicin, a cytotoxic antibiotic from Micromonospora neihuensis. The compound crystallizes as discrete mol­ecules with crystallographic inversion symmetry. Inter­molecular N—H...O hydrogen bonds yield polymeric chains along the c axis. The trimethoxy­phenyl­methyl­ene side chain is found to be in a Z configuration about the C=C double bond.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536805012316/bt6651sup1.cif
Contains datablocks global, I

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536805012316/bt6651Isup2.hkl
Contains datablock I

CCDC reference: 271825

Key indicators

  • Single-crystal X-ray study
  • T = 295 K
  • Mean [sigma](C-C) = 0.005 Å
  • R factor = 0.052
  • wR factor = 0.189
  • Data-to-parameter ratio = 13.4

checkCIF/PLATON results

No syntax errors found



Alert level C PLAT340_ALERT_3_C Low Bond Precision on C-C bonds (x 1000) Ang ... 5 PLAT601_ALERT_2_C Structure Contains Solvent Accessible VOIDS of . 31.00 A   3
0 ALERT level A = In general: serious problem 0 ALERT level B = Potentially serious problem 2 ALERT level C = Check and explain 0 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 1 ALERT type 3 Indicator that the structure quality may be low 0 ALERT type 4 Improvement, methodology, query or suggestion

Computing details top

Data collection: MSC/AFC7 Diffractometer Control Software (Molecular Structure Corporation, 1999); cell refinement: MSC/AFC7 Diffractometer Control Software (Molecular Structure Corporation, 1999); data reduction: TEXSAN for Windows (Molecular Structure Corporation, 2001); program(s) used to solve structure: TEXSAN for Windows; program(s) used to refine structure: TEXSAN for Windows and SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEP-3 (Farrugia, 1997); software used to prepare material for publication: TEXSAN for Windows and PLATON (Spek, 2003).

3,6-(Z,Z)-Bis[(3,4,5-trimethyoxyphenyl)methylene]piperazine-2,5-dione top
Crystal data top
C24H26N2O8F(000) = 992
Mr = 470.47Dx = 1.331 Mg m3
Monoclinic, C2/cMo Kα radiation, λ = 0.7107 Å
Hall symbol: -C 2ycCell parameters from 25 reflections
a = 35.204 (3) Åθ = 18.5–19.9°
b = 5.282 (6) ŵ = 0.10 mm1
c = 12.738 (4) ÅT = 295 K
β = 97.503 (15)°Plate, yellow
V = 2348 (3) Å30.50 × 0.20 × 0.05 mm
Z = 4
Data collection top
Rigaku AFC-7R
diffractometer
Rint = 0.037
Radiation source: Rigaku rotating anodeθmax = 25.0°, θmin = 2.3°
Graphite monochromatorh = 041
ω–2θ scansk = 06
2106 measured reflectionsl = 1515
2070 independent reflections3 standard reflections every 150 reflections
1094 reflections with I > 2σ(I) intensity decay: 0.3%
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)] = 0.052Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.189H-atom parameters constrained
S = 1.03 w = 1/[σ2(Fo2) + (0.0815P)2 + 4.1485P]
where P = (Fo2 + 2Fc2)/3
2070 reflections(Δ/σ)max = 0.001
154 parametersΔρmax = 0.23 e Å3
0 restraintsΔρmin = 0.23 e Å3
Special details top

Experimental. The scan width was (1.68 + 0.35tanθ)° with an ω scan speed of 16° per minute (up to 4 scans to achieve I/σ(I) > 10). Stationary background counts were recorded at each end of the scan, and the scan time:background time ratio was 2:1.

Geometry. Bond distances, angles etc. have been calculated using the rounded fractional coordinates. All su'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 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 > 2σ(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
O10.53698 (7)0.0575 (8)0.69482 (18)0.0693 (12)
O20.36291 (7)0.3712 (5)0.76440 (19)0.0476 (9)
O30.30077 (7)0.0919 (6)0.7169 (2)0.0522 (10)
O40.29522 (7)0.2530 (6)0.5583 (2)0.0556 (10)
N10.48120 (8)0.0309 (7)0.5871 (2)0.0469 (12)
C10.51982 (10)0.0344 (9)0.6049 (3)0.0435 (13)
C20.45894 (10)0.0070 (8)0.4879 (2)0.0395 (13)
C30.42094 (10)0.0229 (8)0.4709 (2)0.0384 (13)
C40.39136 (9)0.0048 (7)0.5411 (2)0.0343 (10)
C50.39360 (9)0.1813 (7)0.6232 (3)0.0353 (11)
C60.36389 (10)0.2043 (7)0.6830 (3)0.0356 (11)
C70.33085 (10)0.0520 (7)0.6613 (3)0.0374 (11)
C80.32854 (10)0.1199 (8)0.5775 (3)0.0402 (14)
C90.35875 (10)0.1416 (8)0.5181 (3)0.0377 (11)
C100.39351 (13)0.5489 (9)0.7836 (3)0.0569 (16)
C110.29179 (13)0.1128 (10)0.7822 (3)0.0607 (17)
C120.29279 (12)0.4492 (9)0.4805 (4)0.0574 (17)
H10.468500.054700.643300.0560*
H30.411100.059100.399500.0460*
H50.415600.285500.637900.0420*
H90.357000.258300.460900.0450*
H10A0.416800.461300.804800.0680*
H10B0.395500.641700.720700.0680*
H10C0.388500.662200.838200.0680*
H11A0.295800.268600.748100.0730*
H11B0.265700.100900.793800.0730*
H11C0.307800.105300.848200.0730*
H12A0.312400.570500.499800.0690*
H12B0.268500.529100.476300.0690*
H12C0.295900.378400.413600.0690*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
O10.0385 (15)0.148 (3)0.0210 (13)0.0108 (18)0.0028 (10)0.0094 (17)
O20.0571 (17)0.0465 (17)0.0404 (15)0.0041 (14)0.0113 (12)0.0121 (13)
O30.0484 (16)0.0506 (18)0.0634 (18)0.0054 (13)0.0287 (13)0.0042 (15)
O40.0383 (15)0.069 (2)0.0607 (18)0.0147 (14)0.0107 (13)0.0196 (17)
N10.0289 (16)0.092 (3)0.0205 (14)0.0032 (17)0.0061 (11)0.0026 (17)
C10.0281 (18)0.077 (3)0.0249 (17)0.0044 (19)0.0018 (13)0.0045 (19)
C20.035 (2)0.061 (3)0.0218 (16)0.0040 (19)0.0013 (13)0.0016 (18)
C30.0330 (19)0.057 (3)0.0252 (16)0.0003 (18)0.0038 (13)0.0008 (17)
C40.0299 (18)0.047 (2)0.0249 (16)0.0023 (17)0.0000 (13)0.0047 (17)
C50.0319 (19)0.045 (2)0.0283 (17)0.0007 (16)0.0008 (14)0.0034 (17)
C60.040 (2)0.036 (2)0.0304 (18)0.0058 (17)0.0029 (15)0.0037 (17)
C70.0341 (19)0.042 (2)0.0376 (19)0.0071 (17)0.0109 (15)0.0065 (18)
C80.032 (2)0.048 (3)0.040 (2)0.0014 (17)0.0021 (15)0.0018 (19)
C90.0313 (19)0.051 (2)0.0304 (18)0.0013 (18)0.0022 (14)0.0047 (18)
C100.068 (3)0.050 (3)0.051 (2)0.006 (2)0.001 (2)0.011 (2)
C110.067 (3)0.066 (3)0.053 (3)0.009 (2)0.023 (2)0.001 (2)
C120.050 (3)0.053 (3)0.066 (3)0.007 (2)0.004 (2)0.012 (2)
Geometric parameters (Å, º) top
O1—C11.229 (5)C6—C71.412 (5)
O2—C61.365 (5)C7—C81.396 (6)
O2—C101.426 (6)C8—C91.388 (5)
O3—C71.365 (5)C3—H30.9500
O3—C111.425 (6)C5—H50.9500
O4—C81.362 (5)C9—H90.9500
O4—C121.429 (6)C10—H10A0.9500
N1—C11.349 (5)C10—H10B0.9500
N1—C21.412 (4)C10—H10C0.9500
N1—H10.9000C11—H11A0.9500
C1—C2i1.486 (5)C11—H11B0.9500
C2—C31.330 (5)C11—H11C0.9500
C3—C41.466 (5)C12—H12A0.9500
C4—C91.383 (5)C12—H12B0.9500
C4—C51.396 (5)C12—H12C0.9500
C5—C61.377 (5)
O1···O1ii3.116 (5)C12···H92.5200
O1···N1ii2.934 (5)H1···C42.8700
O1···C5ii3.208 (6)H1···C52.7000
O2···O32.642 (5)H1···H52.2200
O3···O22.642 (5)H1···O1ii2.1000
O3···O42.708 (5)H3···H92.3900
O4···C112.964 (6)H3···O1i2.3100
O4···O32.708 (5)H3···O2xii2.7900
O4···C12iii3.253 (6)H3···C10xii3.0000
O1···H10Aii2.6800H3···C10vi3.1000
O1···H1ii2.1000H3···H10Axii2.4600
O1···H5ii2.8000H3···H10Cvi2.3400
O1···H3i2.3100H5···N12.8200
O2···H3iv2.7900H5···C23.0200
O2···H9iv2.6100H5···C102.5200
O3···H11Bv2.8400H5···H12.2200
O4···H11A2.4200H5···H10A2.3200
O4···H12Biii2.6800H5···H10B2.3100
N1···C53.275 (6)H5···O1ii2.8000
N1···O1ii2.934 (5)H9···C122.5200
N1···N1i2.748 (5)H9···H32.3900
N1···H52.8200H9···H12A2.3700
C3···C10vi3.506 (7)H9···H12C2.2500
C5···O1ii3.208 (6)H9···O2xii2.6100
C5···N13.275 (6)H10A···C52.7800
C10···C3vii3.506 (7)H10A···H52.3200
C11···C12viii3.422 (8)H10A···O1ii2.6800
C11···O42.964 (6)H10A···H3iv2.4600
C12···O4iii3.253 (6)H10B···C4xi2.9700
C12···C11ix3.422 (8)H10B···C52.7300
C2···H53.0200H10B···C8xi3.0600
C3···H10Cvi2.7000H10B···C9xi2.9600
C4···H10Bx2.9700H10B···H52.3100
C4···H12.8700H10C···C3vii2.7000
C5···H10A2.7800H10C···H3vii2.3400
C5···H12.7000H11A···O42.4200
C5···H10B2.7300H11A···C82.7100
C6···H12Axi3.0100H11B···O3xiii2.8400
C7···H12Axi2.8800H11C···C9iv2.9300
C8···H12Axi3.0900H11C···C12viii2.9800
C8···H10Bx3.0600H11C···H12Aviii2.5700
C8···H11A2.7100H12A···C6x3.0100
C9···H10Bx2.9600H12A···C7x2.8800
C9···H11Cxii2.9300H12A···C8x3.0900
C9···H12A2.7800H12A···C92.7800
C9···H12C2.7300H12A···H92.3700
C10···H52.5200H12A···H11Cix2.5700
C10···H3vii3.1000H12B···O4iii2.6800
C10···H3iv3.0000H12C···C92.7300
C11···H12Civ3.0800H12C···H92.2500
C12···H11Cix2.9800H12C···C11xii3.0800
C6—O2—C10117.5 (3)C4—C9—C8120.8 (4)
C7—O3—C11115.6 (3)C2—C3—H3114.00
C8—O4—C12118.1 (3)C4—C3—H3114.00
C1—N1—C2125.6 (3)C4—C5—H5120.00
C2—N1—H1117.00C6—C5—H5120.00
C1—N1—H1117.00C4—C9—H9120.00
O1—C1—C2i120.9 (3)C8—C9—H9120.00
N1—C1—C2i117.8 (3)O2—C10—H10A109.00
O1—C1—N1121.3 (3)O2—C10—H10B109.00
C1i—C2—C3117.7 (3)O2—C10—H10C109.00
N1—C2—C3125.7 (3)H10A—C10—H10B110.00
N1—C2—C1i116.6 (3)H10A—C10—H10C110.00
C2—C3—C4132.4 (3)H10B—C10—H10C109.00
C5—C4—C9119.8 (3)O3—C11—H11A109.00
C3—C4—C9116.8 (3)O3—C11—H11B109.00
C3—C4—C5123.3 (3)O3—C11—H11C110.00
C4—C5—C6120.1 (3)H11A—C11—H11B109.00
C5—C6—C7120.5 (3)H11A—C11—H11C110.00
O2—C6—C5125.0 (3)H11B—C11—H11C109.00
O2—C6—C7114.5 (3)O4—C12—H12A110.00
C6—C7—C8119.0 (3)O4—C12—H12B109.00
O3—C7—C6119.1 (3)O4—C12—H12C109.00
O3—C7—C8121.7 (3)H12A—C12—H12B109.00
O4—C8—C7115.9 (3)H12A—C12—H12C109.00
O4—C8—C9124.2 (4)H12B—C12—H12C109.00
C7—C8—C9119.9 (3)
C10—O2—C6—C55.3 (5)C2—C3—C4—C9147.4 (5)
C10—O2—C6—C7173.7 (3)C3—C4—C5—C6177.1 (3)
C11—O3—C7—C6116.2 (4)C3—C4—C9—C8177.2 (4)
C11—O3—C7—C869.4 (5)C5—C4—C9—C81.7 (6)
C12—O4—C8—C7173.9 (4)C9—C4—C5—C61.9 (5)
C12—O4—C8—C97.9 (6)C4—C5—C6—C70.6 (6)
C2—N1—C1—O1176.7 (4)C4—C5—C6—O2179.5 (3)
C2—N1—C1—C2i2.7 (7)O2—C6—C7—C8178.2 (3)
C1—N1—C2—C3176.5 (4)O2—C6—C7—O33.7 (5)
C1—N1—C2—C1i2.7 (6)C5—C6—C7—C80.8 (6)
O1—C1—C2i—N1i177.0 (4)C5—C6—C7—O3175.3 (3)
O1—C1—C2i—C3i3.8 (7)O3—C7—C8—O43.0 (5)
N1—C1—C2i—N1i2.5 (6)C6—C7—C8—C91.0 (6)
N1—C1—C2i—C3i176.8 (4)O3—C7—C8—C9175.3 (4)
N1—C2—C3—C43.7 (8)C6—C7—C8—O4177.4 (3)
C1i—C2—C3—C4177.1 (4)C7—C8—C9—C40.2 (6)
C2—C3—C4—C537.3 (7)O4—C8—C9—C4178.5 (4)
Symmetry codes: (i) x+1, y, z+1; (ii) x+1, y, z+3/2; (iii) x+1/2, y1/2, z+1; (iv) x, y, z+1/2; (v) x+1/2, y+1/2, z+3/2; (vi) x, y+1, z1/2; (vii) x, y+1, z+1/2; (viii) x, y1, z+1/2; (ix) x, y1, z1/2; (x) x, y1, z; (xi) x, y+1, z; (xii) x, y, z1/2; (xiii) x+1/2, y1/2, z+3/2.
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N1—H1···O1ii0.902.102.934 (5)154
C3—H3···O1i0.952.312.739 (5)106
C11—H11A···O40.952.422.964 (6)116
Symmetry codes: (i) x+1, y, z+1; (ii) x+1, y, z+3/2.
 

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