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In the title compound, C42H34N2O8·CH4O, the calix­[4]­arene assumes a cone conform­ation. The hydroxyl groups form intramolecular hydrogen bonds to the ether O atoms.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536804020860/tk6185sup1.cif
Contains datablocks I, global

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536804020860/tk6185Isup2.hkl
Contains datablock I

CCDC reference: 251756

Key indicators

  • Single-crystal X-ray study
  • T = 173 K
  • Mean [sigma](C-C) = 0.004 Å
  • Some non-H atoms missing
  • R factor = 0.057
  • wR factor = 0.153
  • Data-to-parameter ratio = 14.4

checkCIF/PLATON results

No syntax errors found



Alert level A PLAT220_ALERT_2_A Large Non-Solvent C Ueq(max)/Ueq(min) ... 6.01 Ratio
Author Response: The phenyl ring C52 to C57 seems to be disordered over two sites or the ring swings about an axis perpendicular to the ring and running through C52. However, we think the description we have chosen works better than refining it as disorder.
PLAT222_ALERT_3_A Large Non-Solvent    H     Ueq(max)/Ueq(min) ...       5.91 Ratio
Author Response: The phenyl ring C52 to C57 seems to be disordered over two sites or the ring swings about an axis perpendicular to the ring and running through C52. However, we think the description we have chosen works better than refining it as disorder.

Alert level B PLAT213_ALERT_2_B Atom C56 has ADP max/min Ratio ............. 4.80 prolat PLAT230_ALERT_2_B Hirshfeld Test Diff for C54 - C55 .. 7.30 su PLAT241_ALERT_2_B Check High U(eq) as Compared to Neighbors for C55 PLAT601_ALERT_2_B Structure Contains Solvent Accessible VOIDS of . 168.00 A   3
Alert level C CHEMW03_ALERT_2_C The ratio of given/expected molecular weight as calculated from the _atom_site* data lies outside the range 0.99 <> 1.01 From the CIF: _cell_formula_units_Z 4 From the CIF: _chemical_formula_weight 726.75 TEST: Calculate formula weight from _atom_site_* atom mass num sum C 12.01 42.00 504.46 H 1.01 34.00 34.27 N 14.01 2.00 28.01 O 16.00 8.00 127.99 Calculated formula weight 694.74 PLAT041_ALERT_1_C Calc. and Rep. SumFormula Strings Differ .... ? PLAT042_ALERT_1_C Calc. and Rep. MoietyFormula Strings Differ .... ? PLAT043_ALERT_1_C Check Reported Molecular Weight ................ 726.75 PLAT044_ALERT_1_C Calculated and Reported Dx Differ .............. ? PLAT068_ALERT_1_C Reported F000 Differs from Calcd (or Missing)... ? PLAT213_ALERT_2_C Atom C54 has ADP max/min Ratio ............. 3.30 prolat PLAT213_ALERT_2_C Atom C55 has ADP max/min Ratio ............. 3.90 prolat PLAT230_ALERT_2_C Hirshfeld Test Diff for C53 - C54 .. 5.28 su PLAT241_ALERT_2_C Check High U(eq) as Compared to Neighbors for C51 PLAT241_ALERT_2_C Check High U(eq) as Compared to Neighbors for C56 PLAT242_ALERT_2_C Check Low U(eq) as Compared to Neighbors for C52 PLAT242_ALERT_2_C Check Low U(eq) as Compared to Neighbors for C53 PLAT242_ALERT_2_C Check Low U(eq) as Compared to Neighbors for C57
Alert level G FORMU01_ALERT_2_G There is a discrepancy between the atom counts in the _chemical_formula_sum and the formula from the _atom_site* data. Atom count from _chemical_formula_sum:C43 H38 N2 O9 Atom count from the _atom_site data: C42 H34 N2 O8 CELLZ01_ALERT_1_G Difference between formula and atom_site contents detected. CELLZ01_ALERT_1_G ALERT: Large difference may be due to a symmetry error - see SYMMG tests From the CIF: _cell_formula_units_Z 4 From the CIF: _chemical_formula_sum C43 H38 N2 O9 TEST: Compare cell contents of formula and atom_site data atom Z*formula cif sites diff C 172.00 168.00 4.00 H 152.00 136.00 16.00 N 8.00 8.00 0.00 O 36.00 32.00 4.00
2 ALERT level A = In general: serious problem 4 ALERT level B = Potentially serious problem 14 ALERT level C = Check and explain 3 ALERT level G = General alerts; check 7 ALERT type 1 CIF construction/syntax error, inconsistent or missing data 15 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: SMART (Siemens, 1995); cell refinement: SMART; data reduction: SAINT (Siemens, 1995); program(s) used to solve structure: SHELXS97 (Sheldrick, 1990); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: XP in SHELXTL-Plus (Sheldrick, 1991); software used to prepare material for publication: SHELXL97.

26,28-Bis(benzyloxy)-25,27-dihydroxy-5,17-dinitrocalix[4]arene top
Crystal data top
C43H38N2O9F(000) = 1528
Mr = 726.75Dx = 1.350 Mg m3
Monoclinic, P21/nMo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ynCell parameters from 510 reflections
a = 10.2000 (8) Åθ = 1–20°
b = 15.254 (1) ŵ = 0.10 mm1
c = 22.986 (2) ÅT = 173 K
β = 90.508 (6)°Plate, yellow
V = 3576.3 (5) Å30.35 × 0.32 × 0.11 mm
Z = 4
Data collection top
Siemens CCD three-circle
diffractometer
4635 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tubeRint = 0.065
Graphite monochromatorθmax = 25.7°, θmin = 1.6°
ω scansh = 1212
67307 measured reflectionsk = 1818
6793 independent reflectionsl = 2828
Refinement top
Refinement on F2Secondary atom site location: difference Fourier map
Least-squares matrix: fullHydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.057H-atom parameters constrained
wR(F2) = 0.153 w = 1/[σ2(Fo2) + (0.0722P)2 + 1.9514P]
where P = (Fo2 + 2Fc2)/3
S = 1.06(Δ/σ)max < 0.001
6793 reflectionsΔρmax = 0.45 e Å3
472 parametersΔρmin = 0.47 e Å3
0 restraintsExtinction correction: SHELXL97, Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
Primary atom site location: structure-invariant direct methodsExtinction coefficient: 0.0021 (5)
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
C10.8258 (2)0.36892 (18)0.32394 (12)0.0409 (7)
H1A0.85500.42070.30150.049*
H1B0.88770.36110.35690.049*
C20.7998 (2)0.22347 (17)0.12386 (11)0.0315 (6)
H2A0.81270.28420.10990.038*
H2B0.86420.18540.10410.038*
C30.3130 (2)0.29171 (17)0.10646 (11)0.0330 (6)
H3A0.33930.34760.08810.040*
H3B0.23620.26860.08480.040*
C40.3538 (2)0.46907 (16)0.29391 (11)0.0343 (6)
H4A0.38960.51340.26680.041*
H4B0.28420.49740.31700.041*
C110.8328 (2)0.28885 (17)0.28510 (11)0.0337 (6)
C120.8267 (2)0.29428 (15)0.22466 (11)0.0295 (5)
C130.8231 (2)0.21983 (15)0.18907 (10)0.0278 (5)
C140.8364 (2)0.13877 (16)0.21659 (11)0.0332 (6)
H140.83670.08680.19380.040*
C150.8491 (2)0.13243 (18)0.27628 (12)0.0393 (6)
H150.86090.07670.29400.047*
C160.8447 (2)0.20606 (18)0.31000 (12)0.0385 (6)
H160.84980.20070.35110.046*
C210.6620 (2)0.19340 (16)0.10874 (10)0.0278 (5)
C220.5562 (2)0.25300 (15)0.11361 (10)0.0287 (5)
O220.58635 (16)0.33624 (11)0.12752 (8)0.0370 (4)
H220.51750.36370.13560.044*
C230.4256 (2)0.22639 (16)0.10275 (10)0.0284 (5)
C240.4017 (2)0.13966 (16)0.08908 (10)0.0287 (5)
H240.31440.11980.08290.034*
C250.5057 (2)0.08185 (15)0.08440 (10)0.0292 (5)
N250.4790 (2)0.00890 (13)0.07038 (9)0.0335 (5)
O2510.56691 (18)0.05394 (12)0.04903 (8)0.0413 (5)
O2520.3705 (2)0.03808 (14)0.08033 (11)0.0652 (7)
C260.6352 (2)0.10793 (16)0.09279 (10)0.0292 (5)
H260.70470.06730.08760.035*
C310.2752 (2)0.30847 (16)0.16911 (11)0.0293 (5)
C320.3171 (2)0.38270 (15)0.19946 (10)0.0280 (5)
C330.2951 (2)0.39319 (16)0.25903 (10)0.0303 (5)
C340.2214 (2)0.32973 (17)0.28682 (12)0.0371 (6)
H340.20360.33610.32710.045*
C350.1731 (2)0.25728 (17)0.25740 (12)0.0381 (6)
H350.12080.21540.27710.046*
C360.2013 (2)0.24628 (17)0.19924 (12)0.0348 (6)
H360.17000.19570.17940.042*
C410.4622 (2)0.43743 (15)0.33438 (10)0.0294 (5)
C420.5863 (2)0.41720 (15)0.31196 (10)0.0299 (5)
O420.59981 (16)0.42841 (11)0.25412 (7)0.0342 (4)
H420.67890.42200.24520.041*
C430.6897 (2)0.38717 (16)0.34796 (11)0.0319 (6)
C440.6653 (2)0.37618 (16)0.40655 (11)0.0328 (6)
H440.73260.35500.43170.039*
C450.5430 (2)0.39598 (16)0.42859 (11)0.0318 (6)
N450.5200 (2)0.38602 (15)0.49083 (9)0.0408 (5)
O4510.41539 (19)0.41010 (15)0.51055 (8)0.0539 (6)
O4520.6077 (2)0.35417 (17)0.52120 (9)0.0662 (7)
C460.4417 (2)0.42710 (16)0.39358 (10)0.0313 (6)
H460.35920.44120.41000.038*
O510.82106 (15)0.37766 (11)0.19969 (8)0.0362 (4)
C510.9484 (3)0.40917 (18)0.18164 (18)0.0612 (10)
H51A0.96350.39180.14070.073*
H51B1.01730.38140.20600.073*
C520.9590 (2)0.50555 (17)0.18673 (13)0.0400 (6)
C530.9287 (3)0.5602 (2)0.14150 (15)0.0567 (8)
H530.89440.53730.10610.068*
C540.9489 (5)0.6516 (3)0.1481 (3)0.111 (2)
H540.92720.69030.11710.134*
C550.9983 (5)0.6839 (3)0.1978 (5)0.167 (5)
H551.01570.74480.20140.201*
C561.0242 (4)0.6275 (5)0.2443 (3)0.138 (3)
H561.05440.65040.28050.166*
C571.0068 (3)0.5438 (3)0.23821 (16)0.0660 (10)
H571.02750.50660.27010.079*
O610.38831 (15)0.44643 (10)0.16951 (7)0.0313 (4)
C610.3048 (2)0.51268 (17)0.14337 (12)0.0376 (6)
H61A0.25840.54520.17430.045*
H61B0.23820.48420.11810.045*
C620.3843 (3)0.57524 (16)0.10805 (11)0.0359 (6)
C630.4979 (3)0.55105 (19)0.07998 (12)0.0465 (7)
H630.53060.49310.08430.056*
C640.5647 (4)0.6106 (2)0.04560 (13)0.0573 (8)
H640.64270.59320.02650.069*
C650.5183 (4)0.6953 (2)0.03902 (13)0.0614 (10)
H650.56440.73590.01550.074*
C660.4061 (4)0.7203 (2)0.06638 (14)0.0589 (9)
H660.37360.77830.06170.071*
C670.3391 (3)0.66061 (18)0.10123 (13)0.0481 (7)
H670.26170.67850.12050.058*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
C10.0314 (13)0.0471 (16)0.0442 (16)0.0069 (12)0.0039 (11)0.0165 (13)
C20.0301 (12)0.0308 (14)0.0337 (14)0.0010 (10)0.0042 (10)0.0040 (11)
C30.0346 (13)0.0339 (14)0.0305 (14)0.0058 (11)0.0063 (10)0.0019 (11)
C40.0451 (15)0.0305 (14)0.0273 (13)0.0092 (11)0.0014 (11)0.0003 (11)
C110.0199 (11)0.0438 (16)0.0374 (15)0.0043 (10)0.0004 (10)0.0141 (12)
C120.0205 (11)0.0246 (13)0.0434 (15)0.0001 (9)0.0036 (10)0.0022 (11)
C130.0208 (11)0.0276 (13)0.0351 (14)0.0002 (9)0.0028 (9)0.0044 (11)
C140.0339 (13)0.0242 (13)0.0413 (15)0.0011 (10)0.0024 (11)0.0049 (11)
C150.0386 (14)0.0339 (15)0.0453 (17)0.0026 (11)0.0033 (12)0.0031 (13)
C160.0329 (13)0.0500 (18)0.0326 (14)0.0013 (12)0.0027 (11)0.0008 (13)
C210.0308 (12)0.0306 (13)0.0221 (12)0.0003 (10)0.0039 (9)0.0007 (10)
C220.0352 (13)0.0253 (13)0.0255 (13)0.0009 (10)0.0009 (10)0.0006 (10)
O220.0322 (9)0.0277 (10)0.0512 (12)0.0036 (7)0.0013 (8)0.0048 (8)
C230.0321 (12)0.0336 (14)0.0195 (12)0.0054 (10)0.0007 (9)0.0012 (10)
C240.0278 (12)0.0338 (14)0.0244 (12)0.0002 (10)0.0000 (9)0.0018 (10)
C250.0358 (13)0.0290 (13)0.0227 (12)0.0004 (10)0.0008 (10)0.0020 (10)
N250.0329 (11)0.0309 (12)0.0366 (12)0.0002 (9)0.0008 (9)0.0006 (10)
O2510.0442 (10)0.0371 (10)0.0426 (11)0.0082 (8)0.0067 (8)0.0040 (9)
O2520.0525 (13)0.0456 (13)0.0978 (19)0.0107 (10)0.0180 (12)0.0085 (12)
C260.0312 (12)0.0307 (14)0.0257 (13)0.0053 (10)0.0036 (10)0.0011 (10)
C310.0230 (11)0.0325 (13)0.0322 (13)0.0084 (10)0.0037 (10)0.0014 (11)
C320.0242 (11)0.0288 (13)0.0311 (13)0.0053 (10)0.0004 (9)0.0054 (10)
C330.0321 (12)0.0296 (13)0.0292 (13)0.0106 (10)0.0003 (10)0.0011 (11)
C340.0351 (14)0.0419 (16)0.0345 (15)0.0111 (12)0.0057 (11)0.0077 (12)
C350.0282 (13)0.0367 (15)0.0494 (17)0.0034 (11)0.0066 (12)0.0101 (13)
C360.0254 (12)0.0328 (14)0.0461 (16)0.0019 (10)0.0014 (11)0.0008 (12)
C410.0363 (13)0.0211 (12)0.0307 (13)0.0026 (10)0.0009 (10)0.0024 (10)
C420.0420 (14)0.0204 (12)0.0276 (13)0.0053 (10)0.0070 (10)0.0038 (10)
O420.0332 (9)0.0389 (10)0.0305 (10)0.0050 (8)0.0070 (7)0.0009 (8)
C430.0296 (12)0.0280 (13)0.0382 (15)0.0063 (10)0.0006 (10)0.0100 (11)
C440.0312 (13)0.0318 (14)0.0355 (14)0.0006 (11)0.0058 (10)0.0064 (11)
C450.0345 (13)0.0306 (14)0.0302 (13)0.0023 (10)0.0010 (10)0.0012 (11)
N450.0427 (13)0.0473 (14)0.0325 (13)0.0023 (11)0.0017 (10)0.0059 (11)
O4510.0476 (12)0.0778 (15)0.0364 (11)0.0088 (11)0.0102 (9)0.0086 (10)
O4520.0566 (13)0.1007 (19)0.0410 (12)0.0157 (13)0.0112 (10)0.0173 (12)
C460.0315 (13)0.0309 (14)0.0316 (14)0.0011 (10)0.0037 (10)0.0017 (11)
O510.0259 (8)0.0265 (9)0.0562 (12)0.0022 (7)0.0079 (8)0.0029 (8)
C510.0461 (17)0.0308 (16)0.107 (3)0.0042 (13)0.0360 (18)0.0016 (16)
C520.0315 (13)0.0319 (15)0.0566 (18)0.0007 (11)0.0060 (12)0.0019 (13)
C530.0430 (17)0.064 (2)0.063 (2)0.0092 (15)0.0035 (15)0.0163 (17)
C540.067 (3)0.064 (3)0.203 (6)0.034 (2)0.045 (3)0.078 (4)
C550.051 (3)0.044 (3)0.408 (15)0.020 (2)0.060 (5)0.048 (5)
C560.060 (3)0.159 (5)0.196 (6)0.073 (4)0.064 (4)0.150 (5)
C570.0367 (16)0.097 (3)0.065 (2)0.0100 (17)0.0098 (15)0.010 (2)
O610.0323 (9)0.0289 (9)0.0326 (9)0.0025 (7)0.0011 (7)0.0078 (7)
C610.0408 (14)0.0338 (14)0.0382 (15)0.0102 (11)0.0017 (11)0.0080 (12)
C620.0516 (16)0.0292 (14)0.0268 (14)0.0009 (12)0.0052 (12)0.0019 (11)
C630.0652 (19)0.0355 (16)0.0390 (16)0.0007 (14)0.0059 (14)0.0015 (13)
C640.080 (2)0.057 (2)0.0353 (17)0.0091 (17)0.0153 (15)0.0002 (15)
C650.103 (3)0.052 (2)0.0290 (16)0.0249 (19)0.0007 (17)0.0110 (14)
C660.099 (3)0.0310 (16)0.0462 (19)0.0013 (17)0.0125 (18)0.0094 (14)
C670.068 (2)0.0338 (16)0.0422 (17)0.0054 (14)0.0056 (14)0.0044 (13)
Geometric parameters (Å, º) top
C1—C111.515 (3)C35—C361.380 (4)
C1—C431.524 (3)C35—H350.9500
C1—H1A0.9900C36—H360.9500
C1—H1B0.9900C41—C461.387 (3)
C2—C211.517 (3)C41—C421.406 (3)
C2—C131.517 (3)C42—O421.349 (3)
C2—H2A0.9900C42—C431.411 (3)
C2—H2B0.9900O42—H420.8400
C3—C311.516 (3)C43—C441.382 (4)
C3—C231.523 (3)C44—C451.384 (3)
C3—H3A0.9900C44—H440.9500
C3—H3B0.9900C45—C461.387 (3)
C4—C411.517 (3)C45—N451.460 (3)
C4—C331.527 (3)N45—O4511.220 (3)
C4—H4A0.9900N45—O4521.229 (3)
C4—H4B0.9900C46—H460.9500
C11—C161.391 (4)O51—C511.450 (3)
C11—C121.393 (4)C51—C521.479 (4)
C12—O511.396 (3)C51—H51A0.9900
C12—C131.400 (3)C51—H51B0.9900
C13—C141.395 (3)C52—C531.366 (4)
C14—C151.380 (4)C52—C571.403 (4)
C14—H140.9500C53—C541.417 (6)
C15—C161.366 (4)C53—H530.9500
C15—H150.9500C54—C551.338 (10)
C16—H160.9500C54—H540.9500
C21—C261.381 (3)C55—C561.396 (11)
C21—C221.416 (3)C55—H550.9500
C22—O221.344 (3)C56—C571.296 (7)
C22—C231.413 (3)C56—H560.9500
O22—H220.8400C57—H570.9500
C23—C241.381 (3)O61—C611.449 (3)
C24—C251.384 (3)C61—C621.496 (4)
C24—H240.9500C61—H61A0.9900
C25—C261.392 (3)C61—H61B0.9900
C25—N251.446 (3)C62—C631.381 (4)
N25—O2521.217 (3)C62—C671.390 (4)
N25—O2511.235 (3)C63—C641.387 (4)
C26—H260.9500C63—H630.9500
C31—C321.395 (3)C64—C651.384 (5)
C31—C361.399 (3)C64—H640.9500
C32—O611.399 (3)C65—C661.365 (5)
C32—C331.399 (3)C65—H650.9500
C33—C341.385 (4)C66—C671.395 (4)
C34—C351.384 (4)C66—H660.9500
C34—H340.9500C67—H670.9500
C11—C1—C43114.1 (2)C36—C35—H35120.2
C11—C1—H1A108.7C34—C35—H35120.2
C43—C1—H1A108.7C35—C36—C31121.0 (2)
C11—C1—H1B108.7C35—C36—H36119.5
C43—C1—H1B108.7C31—C36—H36119.5
H1A—C1—H1B107.6C46—C41—C42118.6 (2)
C21—C2—C13110.60 (19)C46—C41—C4121.5 (2)
C21—C2—H2A109.5C42—C41—C4119.9 (2)
C13—C2—H2A109.5O42—C42—C41115.7 (2)
C21—C2—H2B109.5O42—C42—C43122.5 (2)
C13—C2—H2B109.5C41—C42—C43121.8 (2)
H2A—C2—H2B108.1C42—O42—H42109.5
C31—C3—C23111.20 (19)C44—C43—C42118.1 (2)
C31—C3—H3A109.4C44—C43—C1120.2 (2)
C23—C3—H3A109.4C42—C43—C1121.7 (2)
C31—C3—H3B109.4C43—C44—C45120.1 (2)
C23—C3—H3B109.4C43—C44—H44120.0
H3A—C3—H3B108.0C45—C44—H44120.0
C41—C4—C33111.16 (19)C44—C45—C46122.1 (2)
C41—C4—H4A109.4C44—C45—N45119.3 (2)
C33—C4—H4A109.4C46—C45—N45118.6 (2)
C41—C4—H4B109.4O451—N45—O452122.8 (2)
C33—C4—H4B109.4O451—N45—C45118.8 (2)
H4A—C4—H4B108.0O452—N45—C45118.4 (2)
C16—C11—C12117.9 (2)C41—C46—C45119.4 (2)
C16—C11—C1119.6 (2)C41—C46—H46120.3
C12—C11—C1122.5 (2)C45—C46—H46120.3
C11—C12—O51117.7 (2)C12—O51—C51112.71 (19)
C11—C12—C13122.4 (2)O51—C51—C52111.8 (2)
O51—C12—C13119.9 (2)O51—C51—H51A109.2
C14—C13—C12116.9 (2)C52—C51—H51A109.2
C14—C13—C2119.6 (2)O51—C51—H51B109.2
C12—C13—C2123.4 (2)C52—C51—H51B109.2
C15—C14—C13121.4 (2)H51A—C51—H51B107.9
C15—C14—H14119.3C53—C52—C57117.6 (3)
C13—C14—H14119.3C53—C52—C51122.1 (3)
C16—C15—C14120.2 (3)C57—C52—C51120.3 (3)
C16—C15—H15119.9C52—C53—C54119.2 (4)
C14—C15—H15119.9C52—C53—H53120.4
C15—C16—C11121.1 (2)C54—C53—H53120.4
C15—C16—H16119.5C55—C54—C53120.4 (5)
C11—C16—H16119.5C55—C54—H54119.8
C26—C21—C22118.6 (2)C53—C54—H54119.8
C26—C21—C2121.8 (2)C54—C55—C56119.7 (5)
C22—C21—C2119.6 (2)C54—C55—H55120.2
O22—C22—C23121.8 (2)C56—C55—H55120.2
O22—C22—C21116.9 (2)C57—C56—C55119.9 (6)
C23—C22—C21121.3 (2)C57—C56—H56120.0
C22—O22—H22109.5C55—C56—H56120.0
C24—C23—C22118.7 (2)C56—C57—C52123.2 (5)
C24—C23—C3120.5 (2)C56—C57—H57118.4
C22—C23—C3120.8 (2)C52—C57—H57118.4
C23—C24—C25119.6 (2)C32—O61—C61112.52 (17)
C23—C24—H24120.2O61—C61—C62110.5 (2)
C25—C24—H24120.2O61—C61—H61A109.5
C24—C25—C26122.3 (2)C62—C61—H61A109.5
C24—C25—N25119.0 (2)O61—C61—H61B109.5
C26—C25—N25118.7 (2)C62—C61—H61B109.5
O252—N25—O251122.4 (2)H61A—C61—H61B108.1
O252—N25—C25118.5 (2)C63—C62—C67118.4 (3)
O251—N25—C25119.0 (2)C63—C62—C61123.0 (2)
C21—C26—C25119.5 (2)C67—C62—C61118.5 (3)
C21—C26—H26120.3C62—C63—C64120.7 (3)
C25—C26—H26120.3C62—C63—H63119.7
C32—C31—C36117.8 (2)C64—C63—H63119.7
C32—C31—C3122.2 (2)C65—C64—C63120.3 (3)
C36—C31—C3119.9 (2)C65—C64—H64119.9
C31—C32—O61118.4 (2)C63—C64—H64119.9
C31—C32—C33122.1 (2)C66—C65—C64119.9 (3)
O61—C32—C33119.4 (2)C66—C65—H65120.1
C34—C33—C32117.6 (2)C64—C65—H65120.1
C34—C33—C4120.0 (2)C65—C66—C67119.9 (3)
C32—C33—C4122.4 (2)C65—C66—H66120.0
C35—C34—C33121.7 (2)C67—C66—H66120.0
C35—C34—H34119.2C62—C67—C66120.8 (3)
C33—C34—H34119.2C62—C67—H67119.6
C36—C35—C34119.6 (2)C66—C67—H67119.6
C43—C1—C11—C1682.1 (3)C4—C33—C34—C35176.1 (2)
C43—C1—C11—C1297.3 (3)C33—C34—C35—C361.6 (4)
C16—C11—C12—O51177.0 (2)C34—C35—C36—C311.7 (4)
C1—C11—C12—O513.5 (3)C32—C31—C36—C351.3 (3)
C16—C11—C12—C134.4 (3)C3—C31—C36—C35175.6 (2)
C1—C11—C12—C13175.0 (2)C33—C4—C41—C46103.0 (3)
C11—C12—C13—C144.9 (3)C33—C4—C41—C4276.5 (3)
O51—C12—C13—C14176.55 (19)C46—C41—C42—O42179.9 (2)
C11—C12—C13—C2172.3 (2)C4—C41—C42—O420.3 (3)
O51—C12—C13—C26.2 (3)C46—C41—C42—C430.2 (3)
C21—C2—C13—C1472.0 (3)C4—C41—C42—C43179.7 (2)
C21—C2—C13—C12105.2 (3)O42—C42—C43—C44178.8 (2)
C12—C13—C14—C151.6 (3)C41—C42—C43—C441.3 (3)
C2—C13—C14—C15175.7 (2)O42—C42—C43—C12.5 (4)
C13—C14—C15—C162.1 (4)C41—C42—C43—C1177.4 (2)
C14—C15—C16—C112.6 (4)C11—C1—C43—C44110.8 (3)
C12—C11—C16—C150.5 (4)C11—C1—C43—C4270.5 (3)
C1—C11—C16—C15178.9 (2)C42—C43—C44—C451.2 (3)
C13—C2—C21—C2695.1 (3)C1—C43—C44—C45177.6 (2)
C13—C2—C21—C2281.8 (3)C43—C44—C45—C460.0 (4)
C26—C21—C22—O22178.1 (2)C43—C44—C45—N45178.5 (2)
C2—C21—C22—O224.9 (3)C44—C45—N45—O451174.3 (2)
C26—C21—C22—C230.3 (3)C46—C45—N45—O4514.2 (4)
C2—C21—C22—C23176.8 (2)C44—C45—N45—O4525.2 (4)
O22—C22—C23—C24179.6 (2)C46—C45—N45—O452176.3 (2)
C21—C22—C23—C242.2 (3)C42—C41—C46—C451.0 (3)
O22—C22—C23—C30.0 (3)C4—C41—C46—C45178.5 (2)
C21—C22—C23—C3178.3 (2)C44—C45—C46—C411.2 (4)
C31—C3—C23—C24100.6 (3)N45—C45—C46—C41179.6 (2)
C31—C3—C23—C2278.9 (3)C11—C12—O51—C5196.5 (3)
C22—C23—C24—C252.2 (3)C13—C12—O51—C5184.9 (3)
C3—C23—C24—C25178.3 (2)C12—O51—C51—C52148.1 (3)
C23—C24—C25—C260.3 (4)O51—C51—C52—C5391.8 (4)
C23—C24—C25—N25179.6 (2)O51—C51—C52—C5791.0 (4)
C24—C25—N25—O25222.1 (3)C57—C52—C53—C541.2 (4)
C26—C25—N25—O252157.8 (2)C51—C52—C53—C54176.0 (3)
C24—C25—N25—O251158.1 (2)C52—C53—C54—C550.6 (6)
C26—C25—N25—O25122.0 (3)C53—C54—C55—C563.1 (8)
C22—C21—C26—C252.7 (3)C54—C55—C56—C573.7 (8)
C2—C21—C26—C25174.3 (2)C55—C56—C57—C521.8 (6)
C24—C25—C26—C212.8 (4)C53—C52—C57—C560.6 (5)
N25—C25—C26—C21177.1 (2)C51—C52—C57—C56176.7 (3)
C23—C3—C31—C32100.1 (3)C31—C32—O61—C6190.0 (2)
C23—C3—C31—C3676.7 (3)C33—C32—O61—C6192.8 (2)
C36—C31—C32—O61178.44 (19)C32—O61—C61—C62175.6 (2)
C3—C31—C32—O614.7 (3)O61—C61—C62—C6330.7 (3)
C36—C31—C32—C334.5 (3)O61—C61—C62—C67152.0 (2)
C3—C31—C32—C33172.4 (2)C67—C62—C63—C640.3 (4)
C31—C32—C33—C344.5 (3)C61—C62—C63—C64177.0 (3)
O61—C32—C33—C34178.5 (2)C62—C63—C64—C650.0 (5)
C31—C32—C33—C4172.9 (2)C63—C64—C65—C660.1 (5)
O61—C32—C33—C44.1 (3)C64—C65—C66—C670.5 (5)
C41—C4—C33—C3469.0 (3)C63—C62—C67—C660.6 (4)
C41—C4—C33—C32108.4 (3)C61—C62—C67—C66176.8 (3)
C32—C33—C34—C351.4 (3)C65—C66—C67—C620.7 (5)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
O22—H22···O610.841.992.806 (2)164
O42—H42···O510.841.922.703 (2)155
 

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