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In the title compound, C26H36N4O4, the two phenyl rings are almost parallel, making a dihedral angle of 2.54 (6)°. The piperazine ring adopts a chair conformation, with the substituents on the N atoms both lying in equatorial positions so that the mol­ecule has an extended conformation and is pseudocentrosymmetric. The crystal structure is stabilized by intramolecular and intermolecular O—H...N hydrogen bonds and weak C—H...O interactions.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536802022560/lh6022sup1.cif
Contains datablocks I, global

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536802022560/lh6022Isup2.hkl
Contains datablock I

CCDC reference: 203014

Key indicators

  • Single-crystal X-ray study
  • T = 293 K
  • Mean [sigma](C-C) = 0.003 Å
  • R factor = 0.060
  • wR factor = 0.190
  • Data-to-parameter ratio = 20.0

checkCIF results

No syntax errors found

ADDSYM reports no extra symmetry








Computing details top

Data collection: SMART (Siemens, 1996); cell refinement: SAINT (Siemens, 1996); data reduction: SAINT (Siemens, 1996); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEP-3 (Farrugia, 1997) and PLATON (Spek, 2002); software used to prepare material for publication: SHELXL97 and PARST (Nardelli, 1995).

1,4-Bis{2-hydroxy-3-[N-(2-hydroxyethyl)imino]-5-methylbenzyl}piperazine top
Crystal data top
C26H36N4O4F(000) = 1008
Mr = 468.62Dx = 1.273 Mg m3
Monoclinic, P21/cMo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybcCell parameters from 6435 reflections
a = 9.7575 (2) Åθ = 1.9–28.6°
b = 13.8091 (3) ŵ = 0.09 mm1
c = 18.4270 (1) ÅT = 293 K
β = 99.964 (1)°Block, colourless
V = 2445.45 (7) Å30.48 × 0.38 × 0.22 mm
Z = 4
Data collection top
Siemens SMART CCD area-detector
diffractometer
3721 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tubeRint = 0.043
Graphite monochromatorθmax = 28.7°, θmin = 1.9°
ω scansh = 1311
17219 measured reflectionsk = 1718
6219 independent reflectionsl = 2324
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)] = 0.060Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.190H-atom parameters constrained
S = 1.06 w = 1/[σ2(Fo2) + (0.1P)2]
where P = (Fo2 + 2Fc2)/3
6219 reflections(Δ/σ)max < 0.001
311 parametersΔρmax = 0.28 e Å3
0 restraintsΔρmin = 0.21 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
C10.4111 (2)0.98193 (12)0.20338 (9)0.0330 (4)
C20.47411 (19)1.06918 (13)0.22891 (9)0.0355 (4)
C30.4148 (2)1.15519 (13)0.20150 (10)0.0392 (4)
H30.45781.21310.21800.047*
C40.2948 (2)1.15804 (13)0.15087 (10)0.0419 (5)
C50.2332 (2)1.07062 (13)0.12736 (10)0.0393 (4)
H50.15031.07130.09370.047*
C70.2149 (2)0.89211 (13)0.12458 (9)0.0381 (4)
H7A0.24940.83900.15710.046*
H7B0.11670.90000.12610.046*
C60.29000 (19)0.98249 (13)0.15191 (9)0.0348 (4)
N80.23179 (15)0.86740 (10)0.04911 (7)0.0317 (3)
C90.37406 (18)0.83825 (13)0.04687 (9)0.0370 (4)
H9A0.39940.78460.08040.044*
H9B0.43650.89170.06290.044*
C100.38983 (19)0.80838 (13)0.02988 (9)0.0368 (4)
H10A0.36890.86300.06310.044*
H10B0.48530.78890.03010.044*
N110.29675 (15)0.72850 (10)0.05533 (7)0.0319 (3)
C120.15462 (18)0.75816 (13)0.05392 (9)0.0364 (4)
H12A0.09190.70490.07020.044*
H12B0.13020.81190.08760.044*
C130.13814 (19)0.78819 (13)0.02254 (10)0.0370 (4)
H13A0.04280.80830.02230.044*
H13B0.15760.73340.05560.044*
C140.3143 (2)0.69910 (13)0.12949 (9)0.0377 (4)
H14A0.41260.69050.13040.045*
H14B0.28030.75040.16390.045*
C150.2392 (2)0.60762 (13)0.15399 (9)0.0356 (4)
C160.2960 (2)0.52013 (13)0.12836 (10)0.0401 (4)
H160.38030.52010.09590.048*
C170.2332 (2)0.43273 (14)0.14880 (11)0.0446 (5)
C180.1113 (2)0.43423 (14)0.19768 (11)0.0451 (5)
H180.06760.37590.21250.054*
C190.0504 (2)0.51948 (14)0.22591 (9)0.0384 (4)
C200.1157 (2)0.60701 (13)0.20366 (9)0.0350 (4)
O210.46652 (15)0.89689 (9)0.22920 (7)0.0429 (3)
H210.53580.90690.26040.064*
C220.2301 (3)1.25202 (15)0.12341 (14)0.0619 (6)
H22A0.14711.23980.08830.093*
H22B0.29451.28830.10030.093*
H22C0.20701.28840.16400.093*
C230.5973 (2)1.07195 (14)0.28494 (10)0.0408 (4)
H230.63651.13190.29900.049*
N240.65432 (18)0.99723 (12)0.31571 (8)0.0432 (4)
C250.7698 (2)1.01125 (16)0.37546 (11)0.0499 (5)
H25A0.81391.07300.36950.060*
H25B0.83830.96060.37420.060*
C260.7208 (3)1.00910 (17)0.44802 (11)0.0560 (6)
H26A0.68010.94640.45480.067*
H26B0.79941.01840.48750.067*
O270.62244 (17)1.08137 (12)0.45128 (8)0.0646 (5)
H270.65441.12160.48240.097*
O280.05876 (15)0.69161 (9)0.22974 (7)0.0466 (4)
H280.01200.68100.25980.070*
C290.2981 (3)0.33945 (16)0.11912 (14)0.0670 (7)
H29A0.38210.35280.08510.101*
H29B0.31930.30070.15900.101*
H29C0.23430.30500.09420.101*
C300.0769 (2)0.51578 (15)0.27915 (10)0.0435 (5)
H300.11550.45550.29260.052*
N310.13801 (18)0.58952 (13)0.30820 (8)0.0447 (4)
C320.2608 (2)0.57383 (16)0.36346 (11)0.0490 (5)
H32A0.33150.62110.35740.059*
H32B0.29810.50980.35740.059*
C330.2253 (2)0.58284 (16)0.43874 (11)0.0478 (5)
H33A0.30810.57140.47520.057*
H33B0.19360.64820.44560.057*
O340.12288 (15)0.51790 (12)0.44964 (8)0.0576 (4)
H340.15530.47860.48130.086*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
C10.0459 (11)0.0299 (9)0.0246 (8)0.0015 (7)0.0100 (7)0.0016 (6)
C20.0442 (11)0.0353 (10)0.0275 (8)0.0037 (8)0.0076 (8)0.0027 (7)
C30.0491 (11)0.0323 (10)0.0371 (10)0.0053 (8)0.0102 (8)0.0025 (7)
C40.0516 (12)0.0366 (10)0.0377 (10)0.0016 (9)0.0087 (9)0.0013 (8)
C50.0444 (11)0.0405 (10)0.0327 (9)0.0008 (8)0.0059 (8)0.0027 (8)
C70.0465 (11)0.0383 (10)0.0304 (9)0.0047 (8)0.0091 (8)0.0052 (7)
C60.0426 (10)0.0361 (10)0.0266 (8)0.0044 (8)0.0086 (8)0.0055 (7)
N80.0339 (8)0.0335 (8)0.0270 (7)0.0013 (6)0.0031 (6)0.0060 (6)
C90.0339 (10)0.0407 (10)0.0343 (9)0.0018 (8)0.0003 (7)0.0101 (7)
C100.0337 (10)0.0392 (10)0.0378 (9)0.0045 (8)0.0071 (8)0.0072 (8)
N110.0355 (8)0.0328 (8)0.0270 (7)0.0016 (6)0.0037 (6)0.0049 (6)
C120.0342 (10)0.0398 (10)0.0331 (9)0.0028 (8)0.0001 (7)0.0085 (7)
C130.0332 (10)0.0396 (10)0.0382 (9)0.0043 (8)0.0062 (8)0.0091 (8)
C140.0446 (11)0.0396 (10)0.0300 (9)0.0059 (8)0.0095 (8)0.0058 (7)
C150.0464 (11)0.0358 (10)0.0258 (8)0.0031 (8)0.0102 (8)0.0050 (7)
C160.0468 (11)0.0431 (11)0.0312 (9)0.0008 (9)0.0087 (8)0.0014 (8)
C170.0600 (13)0.0353 (10)0.0396 (10)0.0018 (9)0.0118 (10)0.0016 (8)
C180.0587 (13)0.0368 (11)0.0412 (11)0.0087 (9)0.0124 (10)0.0044 (8)
C190.0474 (11)0.0403 (10)0.0290 (9)0.0055 (8)0.0108 (8)0.0062 (7)
C200.0462 (11)0.0341 (9)0.0261 (8)0.0003 (8)0.0104 (8)0.0043 (7)
O210.0554 (9)0.0351 (7)0.0362 (7)0.0020 (6)0.0021 (6)0.0012 (5)
C220.0678 (16)0.0406 (12)0.0721 (15)0.0041 (11)0.0022 (12)0.0050 (10)
C230.0511 (12)0.0408 (11)0.0301 (9)0.0057 (9)0.0059 (8)0.0055 (8)
N240.0501 (10)0.0494 (10)0.0283 (8)0.0006 (8)0.0014 (7)0.0057 (7)
C250.0509 (13)0.0533 (13)0.0422 (11)0.0009 (10)0.0014 (9)0.0053 (9)
C260.0749 (16)0.0556 (13)0.0332 (10)0.0094 (11)0.0023 (10)0.0055 (9)
O270.0696 (11)0.0687 (11)0.0492 (9)0.0124 (9)0.0073 (8)0.0206 (7)
O280.0570 (9)0.0385 (7)0.0408 (8)0.0028 (6)0.0015 (6)0.0054 (6)
C290.0846 (18)0.0447 (13)0.0701 (16)0.0056 (12)0.0084 (13)0.0111 (11)
C300.0488 (12)0.0480 (12)0.0342 (10)0.0113 (9)0.0089 (9)0.0104 (8)
N310.0464 (10)0.0544 (10)0.0327 (8)0.0044 (8)0.0052 (7)0.0081 (7)
C320.0399 (11)0.0612 (13)0.0447 (11)0.0056 (10)0.0042 (9)0.0098 (10)
C330.0487 (12)0.0532 (12)0.0396 (11)0.0047 (10)0.0022 (9)0.0046 (9)
O340.0514 (9)0.0698 (10)0.0488 (9)0.0100 (8)0.0005 (7)0.0245 (7)
Geometric parameters (Å, º) top
C1—O211.345 (2)C16—H160.9300
C1—C61.381 (3)C17—C181.363 (3)
C1—C21.397 (2)C17—C291.496 (3)
C2—C31.379 (2)C18—C191.379 (3)
C2—C231.443 (3)C18—H180.9300
C3—C41.365 (3)C19—C201.394 (2)
C3—H30.9300C19—C301.444 (3)
C4—C51.384 (3)C20—O281.346 (2)
C4—C221.493 (3)O21—H210.8200
C5—C61.381 (2)C22—H22A0.9600
C5—H50.9300C22—H22B0.9600
C7—N81.469 (2)C22—H22C0.9600
C7—C61.490 (2)C23—N241.260 (2)
C7—H7A0.9700C23—H230.9300
C7—H7B0.9700N24—C251.446 (2)
N8—C91.453 (2)C25—C261.496 (3)
N8—C131.455 (2)C25—H25A0.9700
C9—C101.506 (2)C25—H25B0.9700
C9—H9A0.9700C26—O271.393 (3)
C9—H9B0.9700C26—H26A0.9700
C10—N111.454 (2)C26—H26B0.9700
C10—H10A0.9700O27—H270.8200
C10—H10B0.9700O28—H280.8200
N11—C121.451 (2)C29—H29A0.9600
N11—C141.464 (2)C29—H29B0.9600
C12—C131.504 (2)C29—H29C0.9600
C12—H12A0.9700C30—N311.252 (3)
C12—H12B0.9700C30—H300.9300
C13—H13A0.9700N31—C321.448 (2)
C13—H13B0.9700C32—C331.492 (3)
C14—C151.491 (2)C32—H32A0.9700
C14—H14A0.9700C32—H32B0.9700
C14—H14B0.9700C33—O341.383 (2)
C15—C161.378 (2)C33—H33A0.9700
C15—C201.382 (3)C33—H33B0.9700
C16—C171.376 (3)O34—H340.8200
O21—C1—C6119.4 (2)C17—C16—C15122.78 (19)
O21—C1—C2120.5 (2)C17—C16—H16118.6
C6—C1—C2120.05 (16)C15—C16—H16118.6
C3—C2—C1119.16 (17)C18—C17—C16117.7 (2)
C3—C2—C23118.98 (16)C18—C17—C29121.4 (2)
C1—C2—C23121.83 (16)C16—C17—C29121.0 (2)
C4—C3—C2122.10 (17)C17—C18—C19122.15 (18)
C4—C3—H3118.9C17—C18—H18118.9
C2—C3—H3118.9C19—C18—H18118.9
C3—C4—C5117.61 (17)C18—C19—C20118.94 (17)
C3—C4—C22121.3 (2)C18—C19—C30119.32 (17)
C5—C4—C22121.1 (2)C20—C19—C30121.72 (18)
C6—C5—C4122.55 (18)O28—C20—C15119.3 (2)
C6—C5—H5118.7O28—C20—C19120.5 (2)
C4—C5—H5118.7C15—C20—C19120.12 (17)
N8—C7—C6112.68 (14)C1—O21—H21109.5
N8—C7—H7A109.1C4—C22—H22A109.5
C6—C7—H7A109.1C4—C22—H22B109.5
N8—C7—H7B109.1H22A—C22—H22B109.5
C6—C7—H7B109.1C4—C22—H22C109.5
H7A—C7—H7B107.8H22A—C22—H22C109.5
C5—C6—C1118.50 (16)H22B—C22—H22C109.5
C5—C6—C7118.79 (17)N24—C23—C2123.28 (18)
C1—C6—C7122.65 (16)N24—C23—H23118.4
C9—N8—C13109.3 (1)C2—C23—H23118.4
C9—N8—C7110.8 (1)C23—N24—C25117.3 (2)
C13—N8—C7109.1 (1)N24—C25—C26110.50 (18)
N8—C9—C10110.85 (14)N24—C25—H25A109.6
N8—C9—H9A109.5C26—C25—H25A109.6
C10—C9—H9A109.5N24—C25—H25B109.6
N8—C9—H9B109.5C26—C25—H25B109.6
C10—C9—H9B109.5H25A—C25—H25B108.1
H9A—C9—H9B108.1O27—C26—C25110.70 (17)
N11—C10—C9110.54 (14)O27—C26—H26A109.5
N11—C10—H10A109.5C25—C26—H26A109.5
C9—C10—H10A109.5O27—C26—H26B109.5
N11—C10—H10B109.5C25—C26—H26B109.5
C9—C10—H10B109.5H26A—C26—H26B108.1
H10A—C10—H10B108.1C26—O27—H27109.5
C12—N11—C10109.0 (1)C20—O28—H28109.5
C12—N11—C14111.2 (1)C17—C29—H29A109.5
C10—N11—C14110.1 (1)C17—C29—H29B109.5
N11—C12—C13110.62 (14)H29A—C29—H29B109.5
N11—C12—H12A109.5C17—C29—H29C109.5
C13—C12—H12A109.5H29A—C29—H29C109.5
N11—C12—H12B109.5H29B—C29—H29C109.5
C13—C12—H12B109.5N31—C30—C19123.47 (18)
H12A—C12—H12B108.1N31—C30—H30118.3
N8—C13—C12111.09 (15)C19—C30—H30118.3
N8—C13—H13A109.4C30—N31—C32117.0 (2)
C12—C13—H13A109.4N31—C32—C33110.12 (16)
N8—C13—H13B109.4N31—C32—H32A109.6
C12—C13—H13B109.4C33—C32—H32A109.6
H13A—C13—H13B108.0N31—C32—H32B109.6
N11—C14—C15112.78 (14)C33—C32—H32B109.6
N11—C14—H14A109.0H32A—C32—H32B108.2
C15—C14—H14A109.0O34—C33—C32111.77 (17)
N11—C14—H14B109.0O34—C33—H33A109.3
C15—C14—H14B109.0C32—C33—H33A109.3
H14A—C14—H14B107.8O34—C33—H33B109.3
C16—C15—C20118.34 (17)C32—C33—H33B109.3
C16—C15—C14119.47 (17)H33A—C33—H33B107.9
C20—C15—C14122.17 (16)C33—O34—H34109.5
O21—C1—C2—C3179.90 (16)C12—N11—C14—C1568.4 (2)
C6—C1—C2—C30.7 (3)C10—N11—C14—C15170.7 (2)
O21—C1—C2—C231.9 (3)N11—C14—C15—C1678.3 (2)
C6—C1—C2—C23177.30 (16)N11—C14—C15—C20103.66 (19)
C1—C2—C3—C41.0 (3)C20—C15—C16—C171.6 (3)
C23—C2—C3—C4177.05 (17)C14—C15—C16—C17179.65 (16)
C2—C3—C4—C50.0 (3)C15—C16—C17—C181.4 (3)
C2—C3—C4—C22178.29 (18)C15—C16—C17—C29179.50 (19)
C3—C4—C5—C61.4 (3)C16—C17—C18—C190.5 (3)
C22—C4—C5—C6179.71 (18)C29—C17—C18—C19179.65 (19)
C4—C5—C6—C11.7 (3)C17—C18—C19—C200.1 (3)
C4—C5—C6—C7178.90 (17)C17—C18—C19—C30178.22 (18)
O21—C1—C6—C5178.58 (15)C16—C15—C20—O28179.62 (15)
C2—C1—C6—C50.6 (3)C14—C15—C20—O281.6 (3)
O21—C1—C6—C71.5 (3)C16—C15—C20—C190.9 (3)
C2—C1—C6—C7177.67 (15)C14—C15—C20—C19178.92 (16)
N8—C7—C6—C576.6 (2)C18—C19—C20—O28179.58 (16)
N8—C7—C6—C1106.31 (19)C30—C19—C20—O282.2 (3)
C6—C7—N8—C968.82 (19)C18—C19—C20—C150.1 (3)
C6—C7—N8—C13170.9 (2)C30—C19—C20—C15178.36 (16)
C13—N8—C9—C1057.13 (19)C3—C2—C23—N24176.32 (17)
C7—N8—C9—C10177.32 (14)C1—C2—C23—N241.7 (3)
N8—C9—C10—N1158.9 (2)C2—C23—N24—C25174.66 (16)
C9—C10—N11—C1258.57 (18)C23—N24—C25—C2695.0 (2)
C9—C10—N11—C14179.18 (15)N24—C25—C26—O2759.3 (2)
C10—N11—C12—C1358.37 (19)C18—C19—C30—N31179.08 (18)
C14—N11—C12—C13179.97 (14)C20—C19—C30—N310.8 (3)
C9—N8—C13—C1257.03 (19)C19—C30—N31—C32176.92 (16)
C7—N8—C13—C12178.30 (15)C30—N31—C32—C3399.6 (2)
N11—C12—C13—N858.6 (2)N31—C32—C33—O3458.2 (2)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
O21—H21···N240.821.882.609 (2)148
O28—H28···N310.821.882.608 (2)148
C7—H7A···O210.972.432.848 (2)105
C14—H14B···O280.972.432.837 (2)105
O27—H27···N11i0.822.002.811 (2)171
O34—H34···N8ii0.822.042.852 (2)172
C29—H29A···O27iii0.962.503.388 (3)154
Symmetry codes: (i) x+1, y+1/2, z+1/2; (ii) x, y1/2, z1/2; (iii) x, y+3/2, z1/2.
 

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