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Acta Crystallogr Sect E Struct Rep Online. 2008 December 1; 64(Pt 12): o2488–o2489.
Published online 2008 November 29. doi:  10.1107/S1600536808039548
PMCID: PMC2960136

Ethyl 4-(4-hydroxy­phen­yl)-6-methyl-2-oxo-1,2,3,4-tetra­hydro­pyrimidine-5-carboxyl­ate monohydrate

Abstract

There are three formula units in the asymmetric unit of the title compound, C14H16N2O4·H2O. Mol­ecules are linked by N—H(...)O hydrogen bonds into dimers with the common R 2 2(8) graph-set motif. Between dimers, single N—H(...)O hydrogen bonds are formed between the other N—H group of each pyrimidine ring and the hydroxyl groups. The water mol­ecules accept O—H(...)O hydrogen bonds from the hydroxyl groups and donate hydrogen bonds to the ester groups.

Related literature

For background literature concerning pyrimidine compounds and for synthesis details, see: Kappe (2000 [triangle]); Biginelli (1891 [triangle]); List (2006 [triangle]); Mabry & Ganem (2006 [triangle]).

An external file that holds a picture, illustration, etc.
Object name is e-64-o2488-scheme1.jpg

Experimental

Crystal data

  • C14H16N2O4·H2O
  • M r = 294.30
  • Monoclinic, An external file that holds a picture, illustration, etc.
Object name is e-64-o2488-efi2.jpg
  • a = 11.1583 (15) Å
  • b = 17.773 (2) Å
  • c = 21.686 (3) Å
  • β = 91.448 (2)°
  • V = 4299.3 (10) Å3
  • Z = 12
  • Mo Kα radiation
  • μ = 0.10 mm−1
  • T = 292 (2) K
  • 0.50 × 0.20 × 0.10 mm

Data collection

  • Bruker SMART APEX CCD diffractometer
  • Absorption correction: multi-scan (SADABS; Sheldrick, 1996 [triangle]) T min = 0.906, T max = 0.990
  • 33204 measured reflections
  • 8419 independent reflections
  • 3947 reflections with I > 2σ(I)
  • R int = 0.083

Refinement

  • R[F 2 > 2σ(F 2)] = 0.054
  • wR(F 2) = 0.138
  • S = 0.90
  • 8419 reflections
  • 601 parameters
  • H atoms treated by a mixture of independent and constrained refinement
  • Δρmax = 0.19 e Å−3
  • Δρmin = −0.23 e Å−3

Data collection: SMART (Bruker, 2004 [triangle]); cell refinement: SAINT (Bruker, 2004 [triangle]); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 [triangle]); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 [triangle]); molecular graphics: ORTEP-3 for Windows (Farrugia, 1999 [triangle]) and CAMERON (Watkin et al., 1993 [triangle]); software used to prepare material for publication: PLATON (Spek, 2003 [triangle]).

Table 1
Hydrogen-bond geometry (Å, °)

Supplementary Material

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536808039548/bi2319sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536808039548/bi2319Isup2.hkl

Additional supplementary materials: crystallographic information; 3D view; checkCIF report

Acknowledgments

We thank the Department of Science and Technology, India, for use of the CCD facility set up under the IRHPA–DST program at IISc.

supplementary crystallographic information

Comment

Heterocyclic compounds containing the pyrimidine subunit have been found to have strong bioactivity especially as calcium antagonists. In addition, some of these compounds have also been found to exhibit antihypertensive, antiviral, anti-tumor, antibacterial and anti-inflammatory activity. They can also be potentially used in prevention of coronary artery spasm (Kappe, 2000). The title compound has been synthesized using a Biginelli reaction (Biginelli, 1891), a century-old multi-component reaction (MCR) used to design alkaloids with dihydropyrimidine cores (List, 2006; Mabry & Ganem, 2006).

The compound crystallizes in space group P21/c with an unusual Z value of 12. A search of the Cambridge Structural Database (CSD) yielded only 275 structures having Z = 12, which is less than 0.5% of the 75,822 P21/c structures. In each molecule in the asymmetric unit (Fig. 1), the tetrahydropyrimidine ring adopts a twist boat conformation [C29—N2—C30—C24 = -13.09°, C8—N4—C23—C32 = -14.55°, C38—N6—C33—C37 = 14.90°, C29—N1—C9—C24 = -21.8°, C8—N3—C34—C32 = -31.09°, C38—N5—C52—C37 = 28.07°]. The C—N bond lengths in the tetrahydropyrimidine ring (1.327 (3) to 1.473 (3) Å) are in accordance with those in similar structures. The mean plane of the pyrimidine ring is nearly perpendicular to the phenyl ring [C37—C52—N5 = 110.05°, C14—C34—N3 = 110.25°, C18—C9—N1 = 110.38°].

The structure contains extensive intermolecular N—H···O hydrogen bonding (see Table). Atom N2 acts as a hydrogen-bond donor to O2 to form a centrosymmetric dimer centered at (1/2,1/2,1/2) with the common R22(8) graph-set motif. Atom N6 acts as a hydrogen-bond donor to O6 and N4 acts as a donor to O10 to form another dimeric R22(8) motif. However, such R22(8) motifs are not generated via N1, N3 and N5. Instead, these N atoms form single N—H···O hydrogen bonds to hydroxyl groups: N1 to O5, N3 to O9 and N5 to O1.

Experimental

4-Hydroxybenzaldehyde (0.01 mol), ethyl acetoacetate (0.01 mol), urea (0.02 mol) and p-TSA (0.002 mol) were ground for 4-5 min using a mortar and pestle. The initial syrupy reaction mixture solidified within 15 min. The solid was filtered, washed and recrystallized from a water-acetic acid mixture (yield 95%, m.p. 509–511 K).

1H NMR (DMSO):δ 6.66 (d, 2H), 7.02 (d, 2H), 1.07 (t, 2H), 3.98 (q, 2 H), 2.23 (s, 3 H), 5.08 (s, 1 H), 7.58 (s, 1H), 9.08 (s, 1H), 9.30 (s, 1H).

Refinement

H atoms bound to C atoms were placed geometrically and allowed to ride during subsequent refinement with C—H = 0.93 (3)–0.98 (3) Å and Uiso(H) = 1.2 or 1.5 Ueq(C). H atoms of the hydroxyl groups were placed geometrically with C—H = 0.82 Å and allowed to rotate around the C—O bond with Uiso(H) = 1.5 Ueq(O). H atoms of the water molecules were located in difference Fourier maps and refined freely with isotropic displacement parameters.

Figures

Fig. 1.
The asymmetric unit of the title compound with displacement ellipsoids drawn at the 50% probability level. H atoms are omitted.
Fig. 2.
Partial packing diagram showing the R22(8) motifs formed by N—H···O hydrogen bonds.

Crystal data

C14H16N2O4·H2OF000 = 1872
Mr = 294.30Dx = 1.364 Mg m3
Monoclinic, P21/cMo Kα radiation λ = 0.71073 Å
Hall symbol: -P 2ybcCell parameters from 1328 reflections
a = 11.1583 (15) Åθ = 1.8–26.0º
b = 17.773 (2) ŵ = 0.10 mm1
c = 21.686 (3) ÅT = 292 (2) K
β = 91.448 (2)ºLath, colourless
V = 4299.3 (10) Å30.50 × 0.20 × 0.10 mm
Z = 12

Data collection

Bruker SMART APEX CCD diffractometer8419 independent reflections
Radiation source: fine-focus sealed tube3947 reflections with I > 2σ(I)
Monochromator: graphiteRint = 0.083
T = 292(2) Kθmax = 26.0º
[var phi] and ω scansθmin = 1.8º
Absorption correction: multi-scan(SADABS; Sheldrick, 1996)h = −13→13
Tmin = 0.906, Tmax = 0.990k = −20→21
33204 measured reflectionsl = −26→26

Refinement

Refinement on F2Secondary atom site location: difference Fourier map
Least-squares matrix: fullHydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.054H atoms treated by a mixture of independent and constrained refinement
wR(F2) = 0.138  w = 1/[σ2(Fo2) + (0.0537P)2 + 0.2183P] where P = (Fo2 + 2Fc2)/3
S = 0.90(Δ/σ)max = 0.048
8419 reflectionsΔρmax = 0.19 e Å3
601 parametersΔρmin = −0.23 e Å3
Primary atom site location: structure-invariant direct methodsExtinction correction: none

Special details

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 > 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)

xyzUiso*/Ueq
O10.33773 (18)0.41538 (12)0.11596 (8)0.0621 (8)
O20.57587 (15)0.42885 (10)0.45666 (8)0.0497 (7)
O30.02224 (16)0.37128 (12)0.41500 (9)0.0719 (9)
O40.11134 (15)0.28500 (11)0.35739 (8)0.0557 (7)
N10.45115 (16)0.35440 (12)0.39975 (9)0.0422 (8)
N20.37628 (18)0.45170 (12)0.45626 (9)0.0458 (8)
C90.3345 (2)0.33601 (14)0.37022 (11)0.0389 (9)
C180.3331 (2)0.35869 (14)0.30237 (11)0.0367 (9)
C240.2357 (2)0.37138 (15)0.40681 (11)0.0391 (9)
C270.2886 (2)0.42710 (15)0.28185 (12)0.0425 (10)
C290.4734 (2)0.41183 (15)0.43768 (11)0.0400 (10)
C300.2591 (2)0.42843 (15)0.44647 (11)0.0407 (10)
C350.3341 (2)0.39763 (17)0.17742 (12)0.0452 (10)
C360.2889 (2)0.44681 (15)0.22048 (12)0.0447 (10)
C410.1130 (2)0.34506 (17)0.39467 (12)0.0469 (10)
C430.3778 (2)0.31030 (15)0.25840 (12)0.0461 (10)
C510.3789 (2)0.32967 (16)0.19670 (12)0.0511 (11)
C58−0.0060 (2)0.25637 (19)0.33819 (14)0.0726 (13)
C590.1717 (2)0.47050 (15)0.48439 (12)0.0564 (11)
C630.0100 (3)0.19780 (19)0.29252 (17)0.0982 (16)
O50.66400 (17)0.25970 (11)0.36851 (8)0.0604 (8)
O60.43755 (14)0.22711 (11)0.03821 (8)0.0521 (7)
O70.99348 (15)0.17389 (11)0.07701 (9)0.0656 (8)
O80.90818 (14)0.09252 (10)0.14113 (8)0.0464 (7)
N30.56592 (16)0.15289 (12)0.09325 (9)0.0402 (8)
N40.63647 (17)0.25030 (12)0.03655 (9)0.0458 (8)
C80.5406 (2)0.21040 (15)0.05610 (11)0.0392 (10)
C140.67912 (19)0.17523 (14)0.19033 (11)0.0340 (9)
C170.9035 (2)0.14900 (16)0.09962 (12)0.0424 (10)
C230.7551 (2)0.22858 (15)0.04565 (11)0.0410 (10)
C260.6355 (2)0.13308 (15)0.23857 (11)0.0434 (10)
C310.6696 (2)0.23365 (16)0.30919 (12)0.0426 (10)
C320.7804 (2)0.17388 (14)0.08680 (11)0.0366 (9)
C340.6820 (2)0.14156 (14)0.12561 (10)0.0368 (9)
C390.7103 (2)0.27746 (15)0.26171 (12)0.0451 (10)
C471.0265 (2)0.06549 (16)0.15924 (12)0.0519 (10)
C480.7151 (2)0.24819 (14)0.20283 (11)0.0416 (10)
C550.8393 (2)0.27145 (16)0.00655 (11)0.0544 (10)
C570.6307 (2)0.16154 (16)0.29722 (12)0.0484 (11)
C621.0128 (3)0.01022 (16)0.21043 (14)0.0651 (11)
O90.35723 (18)0.05785 (11)0.14122 (8)0.0603 (8)
O100.58206 (15)0.11471 (10)0.47033 (8)0.0522 (7)
O110.02324 (17)0.06082 (12)0.43805 (10)0.0759 (9)
O120.10976 (14)−0.03730 (11)0.39298 (8)0.0509 (7)
N50.45147 (17)0.03034 (12)0.42832 (9)0.0443 (8)
N60.38344 (17)0.14147 (12)0.46649 (9)0.0440 (8)
C220.3837 (2)−0.01916 (16)0.22853 (13)0.0488 (11)
C250.3366 (2)0.02517 (15)0.33034 (11)0.0369 (9)
C330.2636 (2)0.11928 (15)0.46115 (11)0.0411 (10)
C370.2370 (2)0.05563 (15)0.43094 (11)0.0406 (9)
C380.4785 (2)0.09551 (16)0.45504 (11)0.0410 (10)
C420.3491 (2)0.04858 (17)0.20369 (12)0.0449 (10)
C440.3102 (2)0.10538 (15)0.24164 (12)0.0442 (10)
C490.3046 (2)0.09334 (15)0.30425 (12)0.0420 (10)
C520.3344 (2)0.01124 (15)0.39965 (11)0.0386 (9)
C530.1136 (2)0.02892 (17)0.42254 (12)0.0460 (10)
C540.3758 (2)−0.03085 (15)0.29138 (13)0.0449 (10)
C560.1815 (2)0.17336 (15)0.49137 (12)0.0544 (11)
C60−0.0077 (2)−0.06677 (15)0.37706 (13)0.0553 (11)
C610.0072 (3)−0.13722 (16)0.34069 (14)0.0699 (14)
O130.7780 (2)0.38763 (15)0.38773 (12)0.0812 (10)
O140.2287 (2)0.54269 (15)0.08331 (12)0.0840 (11)
O150.2419 (2)0.17780 (15)0.10108 (11)0.0879 (10)
H10.301350.454820.109600.0932*
H20.388630.493660.475130.0549*
H90.324370.281290.372100.0467*
H110.510350.325310.391740.0506*
H270.257770.460680.310260.0509*
H360.258590.493250.207930.0537*
H430.407750.263690.270720.0553*
H510.410200.296410.168170.0612*
H58A−0.046860.236140.373490.0871*
H58B−0.054420.296760.320700.0871*
H59A0.096800.474870.461890.0845*
H59B0.202570.519790.493440.0845*
H59C0.159410.443870.522230.0845*
H63A0.056110.217160.259260.1474*
H63B−0.066900.181510.276850.1474*
H63C0.051520.155990.311230.1474*
H30.510700.119990.098770.0483*
H40.622660.291800.017240.0550*
H50.704000.298230.372090.0906*
H260.608830.084290.231000.0521*
H340.695650.087300.129660.0441*
H390.734570.326720.269290.0541*
H47A1.076540.107170.172940.0624*
H47B1.064040.041550.124480.0624*
H480.742990.278080.171040.0499*
H55A0.858340.318670.025940.0813*
H55B0.802330.28044−0.033220.0813*
H55C0.911460.242860.001750.0813*
H570.601120.132130.328890.0581*
H62A0.968860.033020.243020.0977*
H62B1.09059−0.004700.225900.0977*
H62C0.97019−0.033190.195280.0977*
H60.398390.186990.477710.0527*
H9A0.317080.094320.130210.0904*
H220.41239−0.057060.203280.0583*
H440.287890.151680.225010.0530*
H490.278680.132030.329520.0503*
H520.31950−0.042430.406420.0464*
H540.39733−0.077410.307810.0538*
H56A0.191010.169200.535350.0815*
H56B0.200540.223680.478840.0815*
H56C0.100090.162030.479360.0815*
H60A−0.05117−0.077330.414240.0662*
H60B−0.05286−0.030090.352890.0662*
H61A0.04801−0.174200.365720.1045*
H61B−0.07023−0.156080.328040.1045*
H61C0.05328−0.126740.304910.1045*
H5110.50667−0.003400.427700.0532*
H13A0.854 (3)0.3808 (19)0.4000 (15)0.109 (14)*
H13B0.730 (3)0.409 (2)0.4129 (16)0.117 (15)*
H14A0.276 (4)0.570 (2)0.0565 (18)0.140 (17)*
H14B0.157 (3)0.555 (2)0.0722 (17)0.121 (16)*
H15A0.297 (4)0.199 (2)0.0682 (17)0.153 (16)*
H15B0.165 (3)0.1797 (18)0.0914 (14)0.096 (13)*

Atomic displacement parameters (Å2)

U11U22U33U12U13U23
O10.0634 (14)0.0856 (17)0.0372 (12)0.0017 (12)−0.0015 (10)0.0022 (10)
O20.0299 (10)0.0717 (14)0.0473 (12)−0.0014 (10)−0.0008 (9)−0.0075 (10)
O30.0325 (12)0.1028 (18)0.0806 (16)−0.0027 (11)0.0056 (10)−0.0294 (13)
O40.0359 (11)0.0668 (14)0.0643 (13)−0.0062 (10)0.0002 (9)−0.0132 (11)
N10.0281 (12)0.0581 (16)0.0401 (13)0.0072 (11)−0.0022 (10)−0.0083 (12)
N20.0324 (13)0.0503 (15)0.0547 (15)0.0007 (11)0.0023 (11)−0.0085 (12)
C90.0346 (15)0.0408 (17)0.0413 (16)−0.0010 (12)0.0000 (12)−0.0005 (13)
C180.0279 (13)0.0398 (17)0.0422 (16)−0.0020 (12)−0.0035 (12)−0.0039 (13)
C240.0309 (14)0.0492 (18)0.0371 (16)−0.0001 (13)0.0020 (12)0.0023 (14)
C270.0368 (15)0.0492 (19)0.0414 (18)0.0023 (13)0.0011 (13)−0.0066 (14)
C290.0313 (16)0.0551 (19)0.0335 (16)−0.0006 (14)0.0015 (12)0.0042 (14)
C300.0316 (15)0.0512 (19)0.0392 (16)0.0011 (13)0.0010 (12)0.0024 (14)
C350.0376 (16)0.062 (2)0.0359 (17)−0.0069 (14)−0.0004 (13)−0.0024 (15)
C360.0392 (16)0.0460 (18)0.0489 (18)0.0012 (13)−0.0010 (13)0.0004 (14)
C410.0368 (16)0.061 (2)0.0431 (18)0.0006 (15)0.0027 (13)0.0029 (15)
C430.0395 (16)0.0473 (18)0.0514 (19)0.0042 (13)−0.0003 (14)−0.0063 (14)
C510.0518 (18)0.060 (2)0.0418 (18)0.0059 (16)0.0056 (14)−0.0144 (16)
C580.0372 (17)0.096 (3)0.084 (2)−0.0118 (17)−0.0087 (16)−0.027 (2)
C590.0444 (17)0.069 (2)0.056 (2)0.0030 (16)0.0080 (14)−0.0133 (16)
C630.057 (2)0.097 (3)0.139 (3)0.011 (2)−0.026 (2)−0.054 (3)
O50.0576 (14)0.0820 (17)0.0417 (12)0.0082 (11)0.0026 (10)−0.0114 (11)
O60.0270 (10)0.0748 (14)0.0543 (12)0.0008 (10)−0.0032 (9)0.0147 (10)
O70.0294 (11)0.0941 (16)0.0734 (14)0.0036 (10)0.0048 (10)0.0304 (12)
O80.0317 (10)0.0578 (13)0.0496 (12)0.0032 (9)−0.0022 (8)0.0079 (10)
N30.0318 (12)0.0496 (15)0.0391 (13)−0.0108 (10)−0.0032 (10)0.0063 (11)
N40.0306 (12)0.0542 (15)0.0527 (14)0.0001 (11)0.0004 (10)0.0168 (12)
C80.0321 (15)0.0518 (19)0.0338 (16)−0.0057 (14)0.0033 (12)0.0001 (14)
C140.0258 (13)0.0406 (17)0.0355 (15)−0.0023 (12)−0.0015 (11)0.0010 (13)
C170.0365 (16)0.0526 (19)0.0381 (16)0.0017 (14)0.0009 (13)−0.0011 (14)
C230.0287 (14)0.0584 (19)0.0359 (16)0.0008 (13)0.0024 (12)0.0008 (14)
C260.0441 (16)0.0421 (17)0.0440 (18)−0.0064 (13)0.0001 (13)0.0040 (14)
C310.0345 (15)0.058 (2)0.0352 (16)0.0096 (14)0.0010 (12)−0.0061 (15)
C320.0282 (14)0.0474 (18)0.0341 (15)0.0012 (12)−0.0030 (11)−0.0003 (13)
C340.0291 (14)0.0411 (16)0.0399 (16)0.0011 (12)−0.0046 (12)0.0035 (13)
C390.0403 (16)0.0453 (18)0.0495 (19)0.0000 (13)−0.0004 (13)−0.0054 (15)
C470.0318 (15)0.067 (2)0.0568 (19)0.0066 (14)−0.0026 (13)0.0089 (16)
C480.0437 (16)0.0440 (18)0.0370 (16)−0.0037 (13)0.0002 (12)0.0037 (14)
C550.0383 (16)0.080 (2)0.0450 (18)−0.0029 (15)0.0054 (13)0.0156 (15)
C570.0512 (18)0.059 (2)0.0354 (17)−0.0001 (15)0.0069 (13)0.0072 (15)
C620.0480 (19)0.070 (2)0.077 (2)0.0000 (16)−0.0039 (16)0.0214 (18)
O90.0626 (14)0.0743 (16)0.0444 (12)−0.0070 (11)0.0098 (10)−0.0001 (10)
O100.0288 (10)0.0685 (14)0.0592 (13)−0.0029 (9)−0.0033 (9)−0.0138 (10)
O110.0315 (12)0.0871 (17)0.1094 (18)−0.0028 (11)0.0055 (11)−0.0312 (13)
O120.0302 (10)0.0586 (14)0.0637 (13)−0.0065 (9)−0.0012 (9)−0.0062 (11)
N50.0310 (12)0.0509 (16)0.0505 (14)0.0057 (11)−0.0108 (10)−0.0023 (12)
N60.0308 (12)0.0519 (15)0.0492 (14)−0.0020 (11)0.0015 (10)−0.0118 (11)
C220.0477 (18)0.051 (2)0.0478 (19)0.0030 (15)0.0062 (14)−0.0099 (15)
C250.0276 (14)0.0390 (17)0.0437 (17)−0.0014 (12)−0.0043 (12)−0.0044 (14)
C330.0301 (14)0.059 (2)0.0342 (15)0.0027 (14)0.0019 (12)0.0018 (14)
C370.0313 (15)0.0489 (18)0.0414 (16)−0.0010 (13)−0.0003 (12)−0.0002 (14)
C380.0361 (16)0.053 (2)0.0339 (16)0.0029 (14)−0.0011 (12)0.0003 (14)
C420.0357 (16)0.061 (2)0.0380 (17)−0.0056 (14)0.0025 (13)0.0009 (16)
C440.0403 (16)0.0462 (18)0.0459 (18)−0.0027 (13)−0.0023 (13)0.0001 (15)
C490.0413 (16)0.0430 (18)0.0413 (17)0.0030 (13)−0.0036 (12)−0.0055 (14)
C520.0264 (14)0.0466 (18)0.0427 (16)−0.0025 (12)−0.0035 (12)−0.0023 (13)
C530.0349 (16)0.055 (2)0.0481 (18)−0.0014 (15)−0.0001 (13)0.0033 (15)
C540.0357 (15)0.0398 (17)0.059 (2)0.0057 (13)−0.0021 (13)−0.0015 (15)
C560.0411 (16)0.068 (2)0.0544 (19)0.0036 (15)0.0084 (14)−0.0106 (15)
C600.0366 (16)0.059 (2)0.070 (2)−0.0095 (14)−0.0065 (14)−0.0077 (16)
C610.056 (2)0.060 (2)0.093 (3)0.0000 (17)−0.0132 (18)−0.0122 (19)
O130.0445 (15)0.109 (2)0.0898 (18)0.0123 (14)−0.0036 (14)−0.0457 (15)
O140.0466 (15)0.102 (2)0.103 (2)−0.0050 (14)−0.0046 (14)0.0502 (16)
O150.0438 (14)0.131 (2)0.0886 (19)−0.0107 (15)−0.0047 (13)0.0552 (16)

Geometric parameters (Å, °)

O1—C351.371 (3)C58—H58B0.97
O2—C291.243 (3)C58—H58A0.97
O3—C411.208 (3)C59—H59A0.96
O4—C411.339 (3)C59—H59C0.96
O4—C581.456 (3)C59—H59B0.96
O1—H10.82C63—H63B0.96
O5—C311.370 (3)C63—H63C0.96
O6—C81.240 (3)C63—H63A0.96
O7—C171.212 (3)C14—C341.527 (3)
O8—C171.349 (3)C14—C261.385 (3)
O8—C471.450 (3)C14—C481.382 (3)
O5—H50.82C17—C321.463 (3)
O9—C421.370 (3)C23—C551.491 (3)
O10—C381.242 (3)C23—C321.345 (4)
O11—C531.212 (3)C26—C571.371 (4)
O12—C601.445 (3)C31—C571.376 (4)
O12—C531.340 (4)C31—C391.377 (4)
O9—H9A0.82C32—C341.514 (3)
O13—H13A0.89 (3)C39—C481.381 (4)
O13—H13B0.86 (3)C47—C621.493 (4)
O14—H14A0.93 (4)C26—H260.93
O14—H14B0.86 (3)C34—H340.98
N1—C291.330 (3)C39—H390.93
N1—C91.473 (3)C47—H47B0.97
N2—C291.364 (3)C47—H47A0.97
N2—C301.383 (3)C48—H480.93
N1—H110.86C55—H55C0.96
N2—H20.86C55—H55A0.96
O15—H15B0.88 (3)C55—H55B0.96
O15—H15A1.03 (4)C57—H570.93
N3—C341.471 (3)C62—H62C0.96
N3—C81.327 (3)C62—H62B0.96
N4—C231.388 (3)C62—H62A0.96
N4—C81.360 (3)C22—C541.384 (4)
N3—H30.86C22—C421.371 (4)
N4—H40.86C25—C541.384 (4)
N5—C521.472 (3)C25—C521.524 (3)
N5—C381.327 (3)C25—C491.380 (4)
N6—C381.367 (3)C33—C561.491 (4)
N6—C331.396 (3)C33—C371.337 (4)
N5—H5110.86C37—C531.464 (3)
N6—H60.86C37—C521.517 (3)
C9—C241.511 (3)C42—C441.379 (4)
C9—C181.525 (3)C44—C491.378 (4)
C18—C271.383 (4)C60—C611.491 (4)
C18—C431.386 (4)C22—H220.93
C24—C301.351 (4)C44—H440.93
C24—C411.464 (3)C49—H490.93
C27—C361.376 (4)C52—H520.98
C30—C591.492 (3)C54—H540.93
C35—C361.384 (4)C56—H56A0.96
C35—C511.369 (4)C56—H56B0.96
C43—C511.382 (4)C56—H56C0.96
C58—C631.451 (5)C60—H60A0.97
C9—H90.98C60—H60B0.97
C27—H270.93C61—H61C0.96
C36—H360.93C61—H61A0.96
C43—H430.93C61—H61B0.96
C51—H510.93
O1···O142.657 (3)C51···H54ii3.00
O2···C8i3.313 (3)C53···H14Bviii3.06 (3)
O2···O132.834 (3)C53···H56C2.67
O2···O9ii3.225 (3)C54···H39vii3.09
O2···N2iii2.882 (3)C56···H60Axi3.06
O3···C592.834 (3)C56···H15Ai3.08 (4)
O3···O13iv2.789 (3)C58···H13Aiv3.04 (3)
O4···C183.068 (3)C60···H14Bviii2.96 (4)
O5···O132.633 (3)H1···H14A2.36
O5···N132 (3)H1···H362.30
O6···N6v2.862 (3)H1···H511ii2.43
O6···O152.747 (3)H1···H14B2.52
O6···C29v3.325 (3)H1···O141.84
O7···C552.858 (3)H2···O2iii2.05
O7···O15vi2.809 (3)H2···H59B2.17
O8···C143.158 (3)H2···C29iii2.94
O9···N33.079 (3)H3···O92.25
O9···O2vii3.225 (3)H3···H9A2.33
O9···O152.627 (3)H4···O10v1.99
O10···O14vii2.752 (3)H4···H55B2.32
O10···N4i2.854 (3)H4···C38v2.88
O11···O14viii2.856 (3)H5···H13B2.17
O11···C562.890 (3)H5···H13A2.30
O12···C253.108 (3)H5···O131.82
O13···O52.633 (3)H5···H392.32
O13···O3vi2.789 (3)H5···H112.26
O13···O22.834 (3)H6···O6i2.05
O14···O11ix2.856 (3)H6···H56B2.30
O14···C60ix3.273 (3)H6···C8i2.93
O14···O10ii2.752 (3)H9···O42.39
O14···O12.657 (3)H9···H432.43
O15···C423.395 (4)H9A···H442.33
O15···O92.627 (3)H9A···H15A2.30
O15···C47iv3.392 (4)H9A···H15B2.41
O15···C443.378 (4)H9A···H32.33
O15···O62.747 (3)H9A···O151.81
O15···O7iv2.809 (3)H11···C313.03
O1···H511ii2.47H11···H52.26
O1···H56Av2.80H11···O52.14
O2···H13B2.02 (3)H13A···O3vi1.91 (3)
O2···H2iii2.05H13A···H52.30
O2···H59Biii2.83H13A···C58vi3.04 (3)
O3···H13Aiv1.91 (3)H13A···C41vi2.96 (3)
O3···H58B2.57H13A···H58Bvi2.51
O3···H58A2.67H13B···O52.91 (4)
O3···H59A2.25H13B···H52.17
O4···H92.39H13B···O22.02 (3)
O5···H112.14H13B···H59Biii2.49
O5···H13B2.91 (4)H13B···C292.93 (3)
O5···H55Bi2.70H14A···C38ii2.79 (4)
O6···H15A1.78 (4)H14A···O10ii1.88 (4)
O6···H6v2.05H14A···H12.36
O7···H15Bvi1.93 (3)H14B···H12.52
O7···H55C2.22H14B···C60ix2.96 (4)
O7···H47A2.55H14B···C53ix3.06 (3)
O7···H47B2.68H14B···O11ix2.02 (3)
O8···H342.38H14B···H60Bix2.52
O9···H32.25H15A···C82.75 (4)
O10···H4i1.99H15A···C56v3.08 (4)
O10···H14Avii1.88 (4)H15A···H9A2.30
O11···H60B2.58H15A···O61.78 (4)
O11···H14Bviii2.02 (3)H15A···H56Bv2.59
O11···H60A2.64H15B···O7iv1.93 (3)
O11···H56C2.18H15B···C17iv2.98 (3)
O12···H522.35H15B···C47iv2.96 (3)
O13···H58Bvi2.89H15B···H9A2.41
O13···H51.82H15B···H47Aiv2.42
O13···H392.82H26···C423.01
O14···H60Aix2.91H26···C36vii2.88
O14···H362.85H26···H342.42
O14···H11.84H26···C27vii3.03
O14···H60Bix2.75H26···H36vii2.54
O15···H59Cv2.89H27···H62Cii2.55
O15···H47Aiv2.75H27···C242.64
O15···H9A1.81H27···C303.01
O15···H442.76H34···H262.42
N1···O532 (3)H34···O82.38
N2···O2iii2.882 (3)H36···O142.85
N3···O93.079 (3)H36···H26ii2.54
N4···O10v2.854 (3)H36···H12.30
N6···O6i2.862 (3)H36···C26ii2.97
C8···O2v3.313 (3)H39···C54ii3.09
C8···C29v3.432 (4)H39···O132.82
C14···O83.158 (3)H39···C22ii3.04
C17···C483.574 (3)H39···H52.32
C18···O43.068 (3)H43···H442.58
C23···C483.466 (3)H43···H92.43
C25···O123.108 (3)H43···C443.08
C26···C36vii3.525 (4)H43···C313.07
C26···C423.594 (3)H44···C433.07
C27···C303.593 (4)H44···O152.76
C27···C413.492 (4)H44···H9A2.33
C29···O6i3.325 (3)H44···H432.58
C29···C8i3.432 (4)H47A···H15Bvi2.42
C30···C273.593 (4)H47A···C44vi2.97
C33···C493.475 (4)H47A···O72.55
C35···C54ii3.527 (3)H47A···O15vi2.75
C36···C26ii3.525 (4)H47B···O72.68
C39···C58vi3.556 (3)H47B···H59Cxii2.50
C41···C273.492 (4)H48···C322.64
C42···O153.395 (4)H48···C232.86
C42···C263.594 (3)H49···H63C2.59
C44···O153.378 (4)H49···C372.64
C47···O15vi3.392 (4)H49···C332.87
C48···C233.466 (3)H52···H542.41
C48···C173.574 (3)H52···O122.35
C49···C333.475 (4)H54···C35vii3.04
C49···C533.565 (4)H54···C51vii3.00
C53···C493.565 (4)H54···H522.41
C54···C35vii3.527 (3)H55A···H61Aii2.55
C55···O72.858 (3)H55B···O5v2.70
C56···O112.890 (3)H55B···H42.32
C58···C39iv3.556 (3)H55C···C172.70
C59···O32.834 (3)H55C···O72.22
C60···O14viii3.273 (3)H56A···O1i2.80
C8···H15A2.75 (4)H56A···H60Axi2.53
C8···H6v2.93H56B···C243.08
C17···H15Bvi2.98 (3)H56B···H62.30
C17···H55C2.70H56B···C412.97
C22···H39vii3.04H56B···H15Ai2.59
C23···H482.86H56C···C532.67
C24···H272.64H56C···O112.18
C24···H56B3.08H58A···O32.67
C26···H36vii2.97H58B···H13Aiv2.51
C27···H62Cii3.03H58B···O13iv2.89
C27···H26ii3.03H58B···C39iv2.91
C29···H2iii2.94H58B···O32.57
C29···H13B2.93 (3)H59A···C412.74
C30···H273.01H59A···O32.25
C31···H433.07H59B···H22.17
C31···H113.03H59B···H13Biii2.49
C32···H482.64H59B···O2iii2.83
C33···H492.87H59C···O15i2.89
C35···H61Bix3.09H59C···H47Bxiii2.50
C35···H54ii3.04H60A···O14viii2.91
C36···H26ii2.88H60A···O112.64
C36···H60Bix3.07H60A···H56Axi2.53
C37···H492.64H60A···C56xi3.06
C38···H4i2.88H60B···O14viii2.75
C38···H14Avii2.79 (4)H60B···C36viii3.07
C38···H511x3.03H60B···O112.58
C39···H58Bvi2.91H60B···H14Bviii2.52
C39···H63Bvi3.03H61A···H55Avii2.55
C41···H59A2.74H61B···C35viii3.09
C41···H13Aiv2.96 (3)H62B···C42vi3.09
C41···H62Cii3.04H62C···C27vii3.03
C41···H56B2.97H62C···H27vii2.55
C42···H62Biv3.09H62C···C41vii3.04
C42···H263.01H63B···C39iv3.03
C43···H443.07H63C···C493.04
C44···H47Aiv2.97H63C···H492.59
C44···H433.08H511···C38x3.03
C47···H15Bvi2.96 (3)H511···O1vii2.47
C49···H63C3.04H511···H1vii2.43
C41—O4—C58116.7 (2)C39—C31—C57119.6 (2)
C35—O1—H1109O5—C31—C57118.1 (2)
C17—O8—C47116.56 (18)C17—C32—C23121.7 (2)
C31—O5—H5109C17—C32—C34118.1 (2)
C53—O12—C60116.77 (18)C23—C32—C34120.0 (2)
C42—O9—H9A109C14—C34—C32113.26 (19)
H13A—O13—H13B118 (3)N3—C34—C32108.97 (18)
H14A—O14—H14B103 (4)N3—C34—C14110.25 (18)
C9—N1—C29126.0 (2)C31—C39—C48120.0 (2)
C29—N2—C30123.7 (2)O8—C47—C62108.1 (2)
C29—N1—H11117C14—C48—C39121.1 (2)
C9—N1—H11117C26—C57—C31120.0 (2)
C29—N2—H2118C14—C26—H26119
C30—N2—H2118C57—C26—H26119
H15A—O15—H15B115 (3)C14—C34—H34108
C8—N3—C34124.5 (2)C32—C34—H34108
C8—N4—C23124.4 (2)N3—C34—H34108
C34—N3—H3118C31—C39—H39120
C8—N3—H3118C48—C39—H39120
C23—N4—H4118O8—C47—H47A110
C8—N4—H4118H47A—C47—H47B108
C38—N5—C52125.1 (2)C62—C47—H47A110
C33—N6—C38124.2 (2)C62—C47—H47B110
C52—N5—H511117O8—C47—H47B110
C38—N5—H511117C14—C48—H48119
C38—N6—H6118C39—C48—H48119
C33—N6—H6118H55A—C55—H55C109
C18—C9—C24114.0 (2)H55A—C55—H55B109
N1—C9—C18110.38 (18)C23—C55—H55A109
N1—C9—C24109.13 (19)C23—C55—H55B109
C9—C18—C27122.5 (2)H55B—C55—H55C109
C27—C18—C43117.2 (2)C23—C55—H55C109
C9—C18—C43120.3 (2)C26—C57—H57120
C9—C24—C41117.6 (2)C31—C57—H57120
C30—C24—C41121.3 (2)C47—C62—H62A109
C9—C24—C30121.0 (2)C47—C62—H62B109
C18—C27—C36121.7 (2)H62A—C62—H62C109
O2—C29—N2120.5 (2)H62A—C62—H62B109
N1—C29—N2116.4 (2)H62B—C62—H62C109
O2—C29—N1123.2 (2)C47—C62—H62C109
C24—C30—C59127.5 (2)C42—C22—C54119.7 (3)
N2—C30—C24119.3 (2)C52—C25—C54119.9 (2)
N2—C30—C59113.2 (2)C49—C25—C52122.4 (2)
C36—C35—C51119.2 (2)C49—C25—C54117.6 (2)
O1—C35—C36122.1 (3)N6—C33—C37118.7 (2)
O1—C35—C51118.7 (2)C37—C33—C56129.0 (2)
C27—C36—C35120.1 (2)N6—C33—C56112.3 (2)
O4—C41—C24111.2 (2)C33—C37—C52120.4 (2)
O3—C41—O4121.9 (2)C33—C37—C53122.1 (2)
O3—C41—C24126.9 (3)C52—C37—C53117.3 (2)
C18—C43—C51121.6 (2)O10—C38—N5123.8 (2)
C35—C51—C43120.2 (2)N5—C38—N6115.6 (2)
O4—C58—C63108.7 (2)O10—C38—N6120.6 (2)
N1—C9—H9108O9—C42—C22118.0 (2)
C24—C9—H9108O9—C42—C44122.1 (3)
C18—C9—H9108C22—C42—C44119.9 (2)
C36—C27—H27119C42—C44—C49119.8 (2)
C18—C27—H27119C25—C49—C44121.5 (2)
C27—C36—H36120N5—C52—C37109.2 (2)
C35—C36—H36120N5—C52—C25110.05 (19)
C18—C43—H43119C25—C52—C37112.7 (2)
C51—C43—H43119O11—C53—O12121.8 (2)
C35—C51—H51120O11—C53—C37126.9 (3)
C43—C51—H51120O12—C53—C37111.3 (2)
C63—C58—H58A110C22—C54—C25121.5 (2)
O4—C58—H58B110O12—C60—C61108.6 (2)
C63—C58—H58B110C42—C22—H22120
O4—C58—H58A110C54—C22—H22120
H58A—C58—H58B108C42—C44—H44120
H59A—C59—H59B109C49—C44—H44120
C30—C59—H59C109C25—C49—H49119
H59A—C59—H59C109C44—C49—H49119
H59B—C59—H59C109C37—C52—H52108
C30—C59—H59B110N5—C52—H52108
C30—C59—H59A109C25—C52—H52108
C58—C63—H63A109C22—C54—H54119
C58—C63—H63C109C25—C54—H54119
C58—C63—H63B110C33—C56—H56A109
H63B—C63—H63C109C33—C56—H56B109
H63A—C63—H63C109H56B—C56—H56C109
H63A—C63—H63B109H56A—C56—H56C109
O6—C8—N4120.5 (2)C33—C56—H56C109
O6—C8—N3123.8 (2)H56A—C56—H56B109
N3—C8—N4115.7 (2)O12—C60—H60A110
C34—C14—C48122.4 (2)O12—C60—H60B110
C26—C14—C34119.9 (2)C61—C60—H60A110
C26—C14—C48117.7 (2)C61—C60—H60B110
O7—C17—O8121.6 (2)H60A—C60—H60B108
O7—C17—C32126.6 (2)C60—C61—H61C109
O8—C17—C32111.9 (2)H61A—C61—H61C110
N4—C23—C55112.9 (2)H61B—C61—H61C109
N4—C23—C32118.6 (2)H61A—C61—H61B109
C32—C23—C55128.5 (2)C60—C61—H61A109
C14—C26—C57121.6 (2)C60—C61—H61B109
O5—C31—C39122.3 (2)
C58—O4—C41—O35.0 (4)C36—C35—C51—C430.6 (4)
C58—O4—C41—C24−175.9 (2)C51—C35—C36—C27−0.4 (4)
C41—O4—C58—C63173.1 (2)C18—C43—C51—C35−0.7 (4)
C47—O8—C17—O72.6 (4)C48—C14—C26—C57−1.7 (3)
C47—O8—C17—C32−177.5 (2)C34—C14—C26—C57−179.5 (2)
C17—O8—C47—C62173.3 (2)C26—C14—C48—C391.5 (3)
C60—O12—C53—O113.7 (4)C34—C14—C48—C39179.3 (2)
C60—O12—C53—C37−174.8 (2)C26—C14—C34—N385.8 (3)
C53—O12—C60—C61175.9 (2)C26—C14—C34—C32−151.9 (2)
C29—N1—C9—C18104.2 (3)C48—C14—C34—N3−92.0 (3)
C9—N1—C29—O2−173.0 (2)C48—C14—C34—C3230.4 (3)
C29—N1—C9—C24−21.8 (3)O7—C17—C32—C34−172.9 (3)
C9—N1—C29—N28.1 (4)O8—C17—C32—C23−178.5 (2)
C29—N2—C30—C59165.2 (2)O7—C17—C32—C231.4 (4)
C30—N2—C29—N111.2 (3)O8—C17—C32—C347.2 (3)
C29—N2—C30—C24−13.1 (4)C55—C23—C32—C171.0 (4)
C30—N2—C29—O2−167.8 (2)N4—C23—C32—C17−178.9 (2)
C8—N3—C34—C32−31.1 (3)N4—C23—C32—C34−4.7 (4)
C34—N3—C8—O6−166.1 (2)C55—C23—C32—C34175.2 (2)
C34—N3—C8—N415.6 (3)C14—C26—C57—C310.1 (4)
C8—N3—C34—C1493.8 (3)O5—C31—C39—C48179.4 (2)
C23—N4—C8—N39.5 (3)C39—C31—C57—C261.7 (4)
C8—N4—C23—C32−14.6 (4)C57—C31—C39—C48−1.9 (3)
C8—N4—C23—C55165.5 (2)O5—C31—C57—C26−179.6 (2)
C23—N4—C8—O6−168.8 (2)C17—C32—C34—C1475.7 (3)
C38—N5—C52—C37−28.1 (3)C23—C32—C34—N324.4 (3)
C38—N5—C52—C2596.2 (3)C23—C32—C34—C14−98.7 (3)
C52—N5—C38—O10−168.4 (2)C17—C32—C34—N3−161.2 (2)
C52—N5—C38—N612.9 (3)C31—C39—C48—C140.3 (3)
C38—N6—C33—C56165.4 (2)C54—C22—C42—O9−179.5 (2)
C33—N6—C38—O10−168.1 (2)C54—C22—C42—C442.0 (4)
C33—N6—C38—N510.7 (3)C42—C22—C54—C25−1.8 (4)
C38—N6—C33—C37−14.9 (4)C52—C25—C49—C44178.3 (2)
N1—C9—C24—C41−165.2 (2)C54—C25—C49—C440.6 (3)
C18—C9—C24—C30−105.1 (3)C49—C25—C52—N5−90.3 (3)
C18—C9—C24—C4170.9 (3)C49—C25—C52—C3731.9 (3)
C24—C9—C18—C2728.6 (3)C54—C25—C52—N587.3 (3)
N1—C9—C18—C27−94.6 (3)C54—C25—C52—C37−150.5 (2)
N1—C9—C18—C4385.2 (3)C49—C25—C54—C220.5 (3)
C24—C9—C18—C43−151.6 (2)C52—C25—C54—C22−177.3 (2)
N1—C9—C24—C3018.8 (3)N6—C33—C37—C52−3.9 (4)
C9—C18—C27—C36179.5 (2)N6—C33—C37—C53−179.2 (2)
C9—C18—C43—C51−179.3 (2)C56—C33—C37—C52175.8 (2)
C43—C18—C27—C36−0.3 (3)C56—C33—C37—C530.5 (4)
C27—C18—C43—C510.5 (3)C33—C37—C52—N522.4 (3)
C9—C24—C41—O3−172.6 (3)C33—C37—C52—C25−100.2 (3)
C9—C24—C41—O48.3 (3)C53—C37—C52—N5−162.1 (2)
C41—C24—C30—N2−179.6 (2)C53—C37—C52—C2575.3 (3)
C41—C24—C30—C592.3 (4)C33—C37—C53—O113.9 (4)
C9—C24—C30—C59178.2 (2)C33—C37—C53—O12−177.6 (2)
C9—C24—C30—N2−3.8 (4)C52—C37—C53—O11−171.5 (3)
C30—C24—C41—O4−175.7 (2)C52—C37—C53—O126.9 (3)
C30—C24—C41—O33.4 (4)O9—C42—C44—C49−179.5 (2)
C18—C27—C36—C350.2 (4)C22—C42—C44—C49−1.0 (4)
O1—C35—C51—C43179.3 (2)C42—C44—C49—C25−0.3 (4)
O1—C35—C36—C27−179.1 (2)

Symmetry codes: (i) x, −y+1/2, z+1/2; (ii) −x+1, y+1/2, −z+1/2; (iii) −x+1, −y+1, −z+1; (iv) x−1, y, z; (v) x, −y+1/2, z−1/2; (vi) x+1, y, z; (vii) −x+1, y−1/2, −z+1/2; (viii) −x, y−1/2, −z+1/2; (ix) −x, y+1/2, −z+1/2; (x) −x+1, −y, −z+1; (xi) −x, −y, −z+1; (xii) x+1, −y+1/2, z−1/2; (xiii) x−1, −y+1/2, z+1/2.

Hydrogen-bond geometry (Å, °)

D—H···AD—HH···AD···AD—H···A
N1—H11···O50.862.143.002 (3)176
N2—H2···O2iii0.862.052.882 (3)162
N3—H3···O90.862.253.079 (3)161
N4—H4···O10v0.861.992.854 (3)177
N5—H511···O1vii0.862.473.278 (3)158
N6—H6···O6i0.862.052.862 (3)157
O1—H1···O140.821.842.657 (3)171
O5—H5···O130.821.822.633 (3)172
O9—H9A···O150.821.812.627 (3)174
O13—H13A···O3vi0.89 (3)1.91 (3)2.789 (3)172 (3)
O13—H13B···O20.86 (3)2.02 (3)2.834 (3)158 (3)
O14—H14A···O10ii0.93 (4)1.88 (4)2.752 (3)156 (4)
O14—H14B···O11ix0.86 (3)2.02 (3)2.856 (3)164 (3)
O15—H15A···O61.03 (4)1.78 (4)2.747 (3)155 (3)
O15—H15B···O7iv0.88 (3)1.93 (3)2.809 (3)173 (3)

Symmetry codes: (iii) −x+1, −y+1, −z+1; (v) x, −y+1/2, z−1/2; (vii) −x+1, y−1/2, −z+1/2; (i) x, −y+1/2, z+1/2; (vi) x+1, y, z; (ii) −x+1, y+1/2, −z+1/2; (ix) −x, y+1/2, −z+1/2; (iv) x−1, y, z.

Footnotes

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: BI2319).

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