organic compounds
Ethyl 4-(4-hydroxyphenyl)-6-methyl-2-oxo-1,2,3,4-tetrahydropyrimidine-5-carboxylate monohydrate
aSolid State and Structural Chemistry Unit, Indian Institute of Science, Bangalore 560 012, India, bF-12, Organic Chemistry Research Laboratory, Ramanujan Ruia College, Matunga (East), Mumbai 400 019, India, and cJai Research Foundation, C-12, Road No. 16, Wagale Industrial Estate, Thane (West) 400 064, India
*Correspondence e-mail: ssctng@sscu.iisc.ernet.in
There are three formula units in the 14H16N2O4·H2O. Molecules are linked by N—H⋯O hydrogen bonds into dimers with the common R22(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.
of the title compound, CRelated literature
For background literature concerning pyrimidine compounds and for synthesis details, see: Kappe (2000); Biginelli (1891); List (2006); Mabry & Ganem (2006).
Experimental
Crystal data
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Refinement
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Data collection: SMART (Bruker, 2004); cell SAINT (Bruker, 2004); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 for Windows (Farrugia, 1999) and CAMERON (Watkin et al., 1993); software used to prepare material for publication: PLATON (Spek, 2003).
Supporting information
10.1107/S1600536808039548/bi2319sup1.cif
contains datablocks global, I. DOI:Structure factors: contains datablock I. DOI: 10.1107/S1600536808039548/bi2319Isup2.hkl
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).
H atoms bound to C atoms were placed geometrically and allowed to ride during subsequent
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.Data collection: SMART (Bruker, 2004); cell
SAINT (Bruker, 2004); data reduction: SAINT (Bruker, 2004); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 for Windows (Farrugia, 1999) and CAMERON (Watkin et al., 1993); software used to prepare material for publication: PLATON (Spek, 2003).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. |
C14H16N2O4·H2O | F(000) = 1872 |
Mr = 294.30 | Dx = 1.364 Mg m−3 |
Monoclinic, P21/c | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: -P 2ybc | Cell parameters from 1328 reflections |
a = 11.1583 (15) Å | θ = 1.8–26.0° |
b = 17.773 (2) Å | µ = 0.10 mm−1 |
c = 21.686 (3) Å | T = 292 K |
β = 91.448 (2)° | Lath, colourless |
V = 4299.3 (10) Å3 | 0.50 × 0.20 × 0.10 mm |
Z = 12 |
Bruker SMART APEX CCD diffractometer | 8419 independent reflections |
Radiation source: fine-focus sealed tube | 3947 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.083 |
ϕ and ω scans | θmax = 26.0°, θmin = 1.8° |
Absorption correction: multi-scan (SADABS; Sheldrick, 1996) | h = −13→13 |
Tmin = 0.906, Tmax = 0.990 | k = −20→21 |
33204 measured reflections | l = −26→26 |
Refinement on F2 | Primary atom site location: structure-invariant direct methods |
Least-squares matrix: full | Secondary atom site location: difference Fourier map |
R[F2 > 2σ(F2)] = 0.054 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.138 | H atoms treated by a mixture of independent and constrained refinement |
S = 0.90 | w = 1/[σ2(Fo2) + (0.0537P)2 + 0.2183P] where P = (Fo2 + 2Fc2)/3 |
8419 reflections | (Δ/σ)max = 0.048 |
601 parameters | Δρmax = 0.19 e Å−3 |
0 restraints | Δρmin = −0.23 e Å−3 |
C14H16N2O4·H2O | V = 4299.3 (10) Å3 |
Mr = 294.30 | Z = 12 |
Monoclinic, P21/c | Mo Kα radiation |
a = 11.1583 (15) Å | µ = 0.10 mm−1 |
b = 17.773 (2) Å | T = 292 K |
c = 21.686 (3) Å | 0.50 × 0.20 × 0.10 mm |
β = 91.448 (2)° |
Bruker SMART APEX CCD diffractometer | 8419 independent reflections |
Absorption correction: multi-scan (SADABS; Sheldrick, 1996) | 3947 reflections with I > 2σ(I) |
Tmin = 0.906, Tmax = 0.990 | Rint = 0.083 |
33204 measured reflections |
R[F2 > 2σ(F2)] = 0.054 | 0 restraints |
wR(F2) = 0.138 | H atoms treated by a mixture of independent and constrained refinement |
S = 0.90 | Δρmax = 0.19 e Å−3 |
8419 reflections | Δρmin = −0.23 e Å−3 |
601 parameters |
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. |
x | y | z | Uiso*/Ueq | ||
O1 | 0.33773 (18) | 0.41538 (12) | 0.11596 (8) | 0.0621 (8) | |
O2 | 0.57587 (15) | 0.42885 (10) | 0.45666 (8) | 0.0497 (7) | |
O3 | 0.02224 (16) | 0.37128 (12) | 0.41500 (9) | 0.0719 (9) | |
O4 | 0.11134 (15) | 0.28500 (11) | 0.35739 (8) | 0.0557 (7) | |
N1 | 0.45115 (16) | 0.35440 (12) | 0.39975 (9) | 0.0422 (8) | |
N2 | 0.37628 (18) | 0.45170 (12) | 0.45626 (9) | 0.0458 (8) | |
C9 | 0.3345 (2) | 0.33601 (14) | 0.37022 (11) | 0.0389 (9) | |
C18 | 0.3331 (2) | 0.35869 (14) | 0.30237 (11) | 0.0367 (9) | |
C24 | 0.2357 (2) | 0.37138 (15) | 0.40681 (11) | 0.0391 (9) | |
C27 | 0.2886 (2) | 0.42710 (15) | 0.28185 (12) | 0.0425 (10) | |
C29 | 0.4734 (2) | 0.41183 (15) | 0.43768 (11) | 0.0400 (10) | |
C30 | 0.2591 (2) | 0.42843 (15) | 0.44647 (11) | 0.0407 (10) | |
C35 | 0.3341 (2) | 0.39763 (17) | 0.17742 (12) | 0.0452 (10) | |
C36 | 0.2889 (2) | 0.44681 (15) | 0.22048 (12) | 0.0447 (10) | |
C41 | 0.1130 (2) | 0.34506 (17) | 0.39467 (12) | 0.0469 (10) | |
C43 | 0.3778 (2) | 0.31030 (15) | 0.25840 (12) | 0.0461 (10) | |
C51 | 0.3789 (2) | 0.32967 (16) | 0.19670 (12) | 0.0511 (11) | |
C58 | −0.0060 (2) | 0.25637 (19) | 0.33819 (14) | 0.0726 (13) | |
C59 | 0.1717 (2) | 0.47050 (15) | 0.48439 (12) | 0.0564 (11) | |
C63 | 0.0100 (3) | 0.19780 (19) | 0.29252 (17) | 0.0982 (16) | |
O5 | 0.66400 (17) | 0.25970 (11) | 0.36851 (8) | 0.0604 (8) | |
O6 | 0.43755 (14) | 0.22711 (11) | 0.03821 (8) | 0.0521 (7) | |
O7 | 0.99348 (15) | 0.17389 (11) | 0.07701 (9) | 0.0656 (8) | |
O8 | 0.90818 (14) | 0.09252 (10) | 0.14113 (8) | 0.0464 (7) | |
N3 | 0.56592 (16) | 0.15289 (12) | 0.09325 (9) | 0.0402 (8) | |
N4 | 0.63647 (17) | 0.25030 (12) | 0.03655 (9) | 0.0458 (8) | |
C8 | 0.5406 (2) | 0.21040 (15) | 0.05610 (11) | 0.0392 (10) | |
C14 | 0.67912 (19) | 0.17523 (14) | 0.19033 (11) | 0.0340 (9) | |
C17 | 0.9035 (2) | 0.14900 (16) | 0.09962 (12) | 0.0424 (10) | |
C23 | 0.7551 (2) | 0.22858 (15) | 0.04565 (11) | 0.0410 (10) | |
C26 | 0.6355 (2) | 0.13308 (15) | 0.23857 (11) | 0.0434 (10) | |
C31 | 0.6696 (2) | 0.23365 (16) | 0.30919 (12) | 0.0426 (10) | |
C32 | 0.7804 (2) | 0.17388 (14) | 0.08680 (11) | 0.0366 (9) | |
C34 | 0.6820 (2) | 0.14156 (14) | 0.12561 (10) | 0.0368 (9) | |
C39 | 0.7103 (2) | 0.27746 (15) | 0.26171 (12) | 0.0451 (10) | |
C47 | 1.0265 (2) | 0.06549 (16) | 0.15924 (12) | 0.0519 (10) | |
C48 | 0.7151 (2) | 0.24819 (14) | 0.20283 (11) | 0.0416 (10) | |
C55 | 0.8393 (2) | 0.27145 (16) | 0.00655 (11) | 0.0544 (10) | |
C57 | 0.6307 (2) | 0.16154 (16) | 0.29722 (12) | 0.0484 (11) | |
C62 | 1.0128 (3) | 0.01022 (16) | 0.21043 (14) | 0.0651 (11) | |
O9 | 0.35723 (18) | 0.05785 (11) | 0.14122 (8) | 0.0603 (8) | |
O10 | 0.58206 (15) | 0.11471 (10) | 0.47033 (8) | 0.0522 (7) | |
O11 | 0.02324 (17) | 0.06082 (12) | 0.43805 (10) | 0.0759 (9) | |
O12 | 0.10976 (14) | −0.03730 (11) | 0.39298 (8) | 0.0509 (7) | |
N5 | 0.45147 (17) | 0.03034 (12) | 0.42832 (9) | 0.0443 (8) | |
N6 | 0.38344 (17) | 0.14147 (12) | 0.46649 (9) | 0.0440 (8) | |
C22 | 0.3837 (2) | −0.01916 (16) | 0.22853 (13) | 0.0488 (11) | |
C25 | 0.3366 (2) | 0.02517 (15) | 0.33034 (11) | 0.0369 (9) | |
C33 | 0.2636 (2) | 0.11928 (15) | 0.46115 (11) | 0.0411 (10) | |
C37 | 0.2370 (2) | 0.05563 (15) | 0.43094 (11) | 0.0406 (9) | |
C38 | 0.4785 (2) | 0.09551 (16) | 0.45504 (11) | 0.0410 (10) | |
C42 | 0.3491 (2) | 0.04858 (17) | 0.20369 (12) | 0.0449 (10) | |
C44 | 0.3102 (2) | 0.10538 (15) | 0.24164 (12) | 0.0442 (10) | |
C49 | 0.3046 (2) | 0.09334 (15) | 0.30425 (12) | 0.0420 (10) | |
C52 | 0.3344 (2) | 0.01124 (15) | 0.39965 (11) | 0.0386 (9) | |
C53 | 0.1136 (2) | 0.02892 (17) | 0.42254 (12) | 0.0460 (10) | |
C54 | 0.3758 (2) | −0.03085 (15) | 0.29138 (13) | 0.0449 (10) | |
C56 | 0.1815 (2) | 0.17336 (15) | 0.49137 (12) | 0.0544 (11) | |
C60 | −0.0077 (2) | −0.06677 (15) | 0.37706 (13) | 0.0553 (11) | |
C61 | 0.0072 (3) | −0.13722 (16) | 0.34069 (14) | 0.0699 (14) | |
O13 | 0.7780 (2) | 0.38763 (15) | 0.38773 (12) | 0.0812 (10) | |
O14 | 0.2287 (2) | 0.54269 (15) | 0.08331 (12) | 0.0840 (11) | |
O15 | 0.2419 (2) | 0.17780 (15) | 0.10108 (11) | 0.0879 (10) | |
H1 | 0.30135 | 0.45482 | 0.10960 | 0.0932* | |
H2 | 0.38863 | 0.49366 | 0.47513 | 0.0549* | |
H9 | 0.32437 | 0.28129 | 0.37210 | 0.0467* | |
H11 | 0.51035 | 0.32531 | 0.39174 | 0.0506* | |
H27 | 0.25777 | 0.46068 | 0.31026 | 0.0509* | |
H36 | 0.25859 | 0.49325 | 0.20793 | 0.0537* | |
H43 | 0.40775 | 0.26369 | 0.27072 | 0.0553* | |
H51 | 0.41020 | 0.29641 | 0.16817 | 0.0612* | |
H58A | −0.04686 | 0.23614 | 0.37349 | 0.0871* | |
H58B | −0.05442 | 0.29676 | 0.32070 | 0.0871* | |
H59A | 0.09680 | 0.47487 | 0.46189 | 0.0845* | |
H59B | 0.20257 | 0.51979 | 0.49344 | 0.0845* | |
H59C | 0.15941 | 0.44387 | 0.52223 | 0.0845* | |
H63A | 0.05611 | 0.21716 | 0.25926 | 0.1474* | |
H63B | −0.06690 | 0.18151 | 0.27685 | 0.1474* | |
H63C | 0.05152 | 0.15599 | 0.31123 | 0.1474* | |
H3 | 0.51070 | 0.11999 | 0.09877 | 0.0483* | |
H4 | 0.62266 | 0.29180 | 0.01724 | 0.0550* | |
H5 | 0.70400 | 0.29823 | 0.37209 | 0.0906* | |
H26 | 0.60883 | 0.08429 | 0.23100 | 0.0521* | |
H34 | 0.69565 | 0.08730 | 0.12966 | 0.0441* | |
H39 | 0.73457 | 0.32672 | 0.26929 | 0.0541* | |
H47A | 1.07654 | 0.10717 | 0.17294 | 0.0624* | |
H47B | 1.06404 | 0.04155 | 0.12448 | 0.0624* | |
H48 | 0.74299 | 0.27808 | 0.17104 | 0.0499* | |
H55A | 0.85834 | 0.31867 | 0.02594 | 0.0813* | |
H55B | 0.80233 | 0.28044 | −0.03322 | 0.0813* | |
H55C | 0.91146 | 0.24286 | 0.00175 | 0.0813* | |
H57 | 0.60112 | 0.13213 | 0.32889 | 0.0581* | |
H62A | 0.96886 | 0.03302 | 0.24302 | 0.0977* | |
H62B | 1.09059 | −0.00470 | 0.22590 | 0.0977* | |
H62C | 0.97019 | −0.03319 | 0.19528 | 0.0977* | |
H6 | 0.39839 | 0.18699 | 0.47771 | 0.0527* | |
H9A | 0.31708 | 0.09432 | 0.13021 | 0.0904* | |
H22 | 0.41239 | −0.05706 | 0.20328 | 0.0583* | |
H44 | 0.28789 | 0.15168 | 0.22501 | 0.0530* | |
H49 | 0.27868 | 0.13203 | 0.32952 | 0.0503* | |
H52 | 0.31950 | −0.04243 | 0.40642 | 0.0464* | |
H54 | 0.39733 | −0.07741 | 0.30781 | 0.0538* | |
H56A | 0.19101 | 0.16920 | 0.53535 | 0.0815* | |
H56B | 0.20054 | 0.22368 | 0.47884 | 0.0815* | |
H56C | 0.10009 | 0.16203 | 0.47936 | 0.0815* | |
H60A | −0.05117 | −0.07733 | 0.41424 | 0.0662* | |
H60B | −0.05286 | −0.03009 | 0.35289 | 0.0662* | |
H61A | 0.04801 | −0.17420 | 0.36572 | 0.1045* | |
H61B | −0.07023 | −0.15608 | 0.32804 | 0.1045* | |
H61C | 0.05328 | −0.12674 | 0.30491 | 0.1045* | |
H511 | 0.50667 | −0.00340 | 0.42770 | 0.0532* | |
H13A | 0.854 (3) | 0.3808 (19) | 0.4000 (15) | 0.109 (14)* | |
H13B | 0.730 (3) | 0.409 (2) | 0.4129 (16) | 0.117 (15)* | |
H14A | 0.276 (4) | 0.570 (2) | 0.0565 (18) | 0.140 (17)* | |
H14B | 0.157 (3) | 0.555 (2) | 0.0722 (17) | 0.121 (16)* | |
H15A | 0.297 (4) | 0.199 (2) | 0.0682 (17) | 0.153 (16)* | |
H15B | 0.165 (3) | 0.1797 (18) | 0.0914 (14) | 0.096 (13)* |
U11 | U22 | U33 | U12 | U13 | U23 | |
O1 | 0.0634 (14) | 0.0856 (17) | 0.0372 (12) | 0.0017 (12) | −0.0015 (10) | 0.0022 (10) |
O2 | 0.0299 (10) | 0.0717 (14) | 0.0473 (12) | −0.0014 (10) | −0.0008 (9) | −0.0075 (10) |
O3 | 0.0325 (12) | 0.1028 (18) | 0.0806 (16) | −0.0027 (11) | 0.0056 (10) | −0.0294 (13) |
O4 | 0.0359 (11) | 0.0668 (14) | 0.0643 (13) | −0.0062 (10) | 0.0002 (9) | −0.0132 (11) |
N1 | 0.0281 (12) | 0.0581 (16) | 0.0401 (13) | 0.0072 (11) | −0.0022 (10) | −0.0083 (12) |
N2 | 0.0324 (13) | 0.0503 (15) | 0.0547 (15) | 0.0007 (11) | 0.0023 (11) | −0.0085 (12) |
C9 | 0.0346 (15) | 0.0408 (17) | 0.0413 (16) | −0.0010 (12) | 0.0000 (12) | −0.0005 (13) |
C18 | 0.0279 (13) | 0.0398 (17) | 0.0422 (16) | −0.0020 (12) | −0.0035 (12) | −0.0039 (13) |
C24 | 0.0309 (14) | 0.0492 (18) | 0.0371 (16) | −0.0001 (13) | 0.0020 (12) | 0.0023 (14) |
C27 | 0.0368 (15) | 0.0492 (19) | 0.0414 (18) | 0.0023 (13) | 0.0011 (13) | −0.0066 (14) |
C29 | 0.0313 (16) | 0.0551 (19) | 0.0335 (16) | −0.0006 (14) | 0.0015 (12) | 0.0042 (14) |
C30 | 0.0316 (15) | 0.0512 (19) | 0.0392 (16) | 0.0011 (13) | 0.0010 (12) | 0.0024 (14) |
C35 | 0.0376 (16) | 0.062 (2) | 0.0359 (17) | −0.0069 (14) | −0.0004 (13) | −0.0024 (15) |
C36 | 0.0392 (16) | 0.0460 (18) | 0.0489 (18) | 0.0012 (13) | −0.0010 (13) | 0.0004 (14) |
C41 | 0.0368 (16) | 0.061 (2) | 0.0431 (18) | 0.0006 (15) | 0.0027 (13) | 0.0029 (15) |
C43 | 0.0395 (16) | 0.0473 (18) | 0.0514 (19) | 0.0042 (13) | −0.0003 (14) | −0.0063 (14) |
C51 | 0.0518 (18) | 0.060 (2) | 0.0418 (18) | 0.0059 (16) | 0.0056 (14) | −0.0144 (16) |
C58 | 0.0372 (17) | 0.096 (3) | 0.084 (2) | −0.0118 (17) | −0.0087 (16) | −0.027 (2) |
C59 | 0.0444 (17) | 0.069 (2) | 0.056 (2) | 0.0030 (16) | 0.0080 (14) | −0.0133 (16) |
C63 | 0.057 (2) | 0.097 (3) | 0.139 (3) | 0.011 (2) | −0.026 (2) | −0.054 (3) |
O5 | 0.0576 (14) | 0.0820 (17) | 0.0417 (12) | 0.0082 (11) | 0.0026 (10) | −0.0114 (11) |
O6 | 0.0270 (10) | 0.0748 (14) | 0.0543 (12) | 0.0008 (10) | −0.0032 (9) | 0.0147 (10) |
O7 | 0.0294 (11) | 0.0941 (16) | 0.0734 (14) | 0.0036 (10) | 0.0048 (10) | 0.0304 (12) |
O8 | 0.0317 (10) | 0.0578 (13) | 0.0496 (12) | 0.0032 (9) | −0.0022 (8) | 0.0079 (10) |
N3 | 0.0318 (12) | 0.0496 (15) | 0.0391 (13) | −0.0108 (10) | −0.0032 (10) | 0.0063 (11) |
N4 | 0.0306 (12) | 0.0542 (15) | 0.0527 (14) | 0.0001 (11) | 0.0004 (10) | 0.0168 (12) |
C8 | 0.0321 (15) | 0.0518 (19) | 0.0338 (16) | −0.0057 (14) | 0.0033 (12) | 0.0001 (14) |
C14 | 0.0258 (13) | 0.0406 (17) | 0.0355 (15) | −0.0023 (12) | −0.0015 (11) | 0.0010 (13) |
C17 | 0.0365 (16) | 0.0526 (19) | 0.0381 (16) | 0.0017 (14) | 0.0009 (13) | −0.0011 (14) |
C23 | 0.0287 (14) | 0.0584 (19) | 0.0359 (16) | 0.0008 (13) | 0.0024 (12) | 0.0008 (14) |
C26 | 0.0441 (16) | 0.0421 (17) | 0.0440 (18) | −0.0064 (13) | 0.0001 (13) | 0.0040 (14) |
C31 | 0.0345 (15) | 0.058 (2) | 0.0352 (16) | 0.0096 (14) | 0.0010 (12) | −0.0061 (15) |
C32 | 0.0282 (14) | 0.0474 (18) | 0.0341 (15) | 0.0012 (12) | −0.0030 (11) | −0.0003 (13) |
C34 | 0.0291 (14) | 0.0411 (16) | 0.0399 (16) | 0.0011 (12) | −0.0046 (12) | 0.0035 (13) |
C39 | 0.0403 (16) | 0.0453 (18) | 0.0495 (19) | 0.0000 (13) | −0.0004 (13) | −0.0054 (15) |
C47 | 0.0318 (15) | 0.067 (2) | 0.0568 (19) | 0.0066 (14) | −0.0026 (13) | 0.0089 (16) |
C48 | 0.0437 (16) | 0.0440 (18) | 0.0370 (16) | −0.0037 (13) | 0.0002 (12) | 0.0037 (14) |
C55 | 0.0383 (16) | 0.080 (2) | 0.0450 (18) | −0.0029 (15) | 0.0054 (13) | 0.0156 (15) |
C57 | 0.0512 (18) | 0.059 (2) | 0.0354 (17) | −0.0001 (15) | 0.0069 (13) | 0.0072 (15) |
C62 | 0.0480 (19) | 0.070 (2) | 0.077 (2) | 0.0000 (16) | −0.0039 (16) | 0.0214 (18) |
O9 | 0.0626 (14) | 0.0743 (16) | 0.0444 (12) | −0.0070 (11) | 0.0098 (10) | −0.0001 (10) |
O10 | 0.0288 (10) | 0.0685 (14) | 0.0592 (13) | −0.0029 (9) | −0.0033 (9) | −0.0138 (10) |
O11 | 0.0315 (12) | 0.0871 (17) | 0.1094 (18) | −0.0028 (11) | 0.0055 (11) | −0.0312 (13) |
O12 | 0.0302 (10) | 0.0586 (14) | 0.0637 (13) | −0.0065 (9) | −0.0012 (9) | −0.0062 (11) |
N5 | 0.0310 (12) | 0.0509 (16) | 0.0505 (14) | 0.0057 (11) | −0.0108 (10) | −0.0023 (12) |
N6 | 0.0308 (12) | 0.0519 (15) | 0.0492 (14) | −0.0020 (11) | 0.0015 (10) | −0.0118 (11) |
C22 | 0.0477 (18) | 0.051 (2) | 0.0478 (19) | 0.0030 (15) | 0.0062 (14) | −0.0099 (15) |
C25 | 0.0276 (14) | 0.0390 (17) | 0.0437 (17) | −0.0014 (12) | −0.0043 (12) | −0.0044 (14) |
C33 | 0.0301 (14) | 0.059 (2) | 0.0342 (15) | 0.0027 (14) | 0.0019 (12) | 0.0018 (14) |
C37 | 0.0313 (15) | 0.0489 (18) | 0.0414 (16) | −0.0010 (13) | −0.0003 (12) | −0.0002 (14) |
C38 | 0.0361 (16) | 0.053 (2) | 0.0339 (16) | 0.0029 (14) | −0.0011 (12) | 0.0003 (14) |
C42 | 0.0357 (16) | 0.061 (2) | 0.0380 (17) | −0.0056 (14) | 0.0025 (13) | 0.0009 (16) |
C44 | 0.0403 (16) | 0.0462 (18) | 0.0459 (18) | −0.0027 (13) | −0.0023 (13) | 0.0001 (15) |
C49 | 0.0413 (16) | 0.0430 (18) | 0.0413 (17) | 0.0030 (13) | −0.0036 (12) | −0.0055 (14) |
C52 | 0.0264 (14) | 0.0466 (18) | 0.0427 (16) | −0.0025 (12) | −0.0035 (12) | −0.0023 (13) |
C53 | 0.0349 (16) | 0.055 (2) | 0.0481 (18) | −0.0014 (15) | −0.0001 (13) | 0.0033 (15) |
C54 | 0.0357 (15) | 0.0398 (17) | 0.059 (2) | 0.0057 (13) | −0.0021 (13) | −0.0015 (15) |
C56 | 0.0411 (16) | 0.068 (2) | 0.0544 (19) | 0.0036 (15) | 0.0084 (14) | −0.0106 (15) |
C60 | 0.0366 (16) | 0.059 (2) | 0.070 (2) | −0.0095 (14) | −0.0065 (14) | −0.0077 (16) |
C61 | 0.056 (2) | 0.060 (2) | 0.093 (3) | 0.0000 (17) | −0.0132 (18) | −0.0122 (19) |
O13 | 0.0445 (15) | 0.109 (2) | 0.0898 (18) | 0.0123 (14) | −0.0036 (14) | −0.0457 (15) |
O14 | 0.0466 (15) | 0.102 (2) | 0.103 (2) | −0.0050 (14) | −0.0046 (14) | 0.0502 (16) |
O15 | 0.0438 (14) | 0.131 (2) | 0.0886 (19) | −0.0107 (15) | −0.0047 (13) | 0.0552 (16) |
O1—C35 | 1.371 (3) | C58—H58B | 0.97 |
O2—C29 | 1.243 (3) | C58—H58A | 0.97 |
O3—C41 | 1.208 (3) | C59—H59A | 0.96 |
O4—C41 | 1.339 (3) | C59—H59C | 0.96 |
O4—C58 | 1.456 (3) | C59—H59B | 0.96 |
O1—H1 | 0.82 | C63—H63B | 0.96 |
O5—C31 | 1.370 (3) | C63—H63C | 0.96 |
O6—C8 | 1.240 (3) | C63—H63A | 0.96 |
O7—C17 | 1.212 (3) | C14—C34 | 1.527 (3) |
O8—C17 | 1.349 (3) | C14—C26 | 1.385 (3) |
O8—C47 | 1.450 (3) | C14—C48 | 1.382 (3) |
O5—H5 | 0.82 | C17—C32 | 1.463 (3) |
O9—C42 | 1.370 (3) | C23—C55 | 1.491 (3) |
O10—C38 | 1.242 (3) | C23—C32 | 1.345 (4) |
O11—C53 | 1.212 (3) | C26—C57 | 1.371 (4) |
O12—C60 | 1.445 (3) | C31—C57 | 1.376 (4) |
O12—C53 | 1.340 (4) | C31—C39 | 1.377 (4) |
O9—H9A | 0.82 | C32—C34 | 1.514 (3) |
O13—H13A | 0.89 (3) | C39—C48 | 1.381 (4) |
O13—H13B | 0.86 (3) | C47—C62 | 1.493 (4) |
O14—H14A | 0.93 (4) | C26—H26 | 0.93 |
O14—H14B | 0.86 (3) | C34—H34 | 0.98 |
N1—C29 | 1.330 (3) | C39—H39 | 0.93 |
N1—C9 | 1.473 (3) | C47—H47B | 0.97 |
N2—C29 | 1.364 (3) | C47—H47A | 0.97 |
N2—C30 | 1.383 (3) | C48—H48 | 0.93 |
N1—H11 | 0.86 | C55—H55C | 0.96 |
N2—H2 | 0.86 | C55—H55A | 0.96 |
O15—H15B | 0.88 (3) | C55—H55B | 0.96 |
O15—H15A | 1.03 (4) | C57—H57 | 0.93 |
N3—C34 | 1.471 (3) | C62—H62C | 0.96 |
N3—C8 | 1.327 (3) | C62—H62B | 0.96 |
N4—C23 | 1.388 (3) | C62—H62A | 0.96 |
N4—C8 | 1.360 (3) | C22—C54 | 1.384 (4) |
N3—H3 | 0.86 | C22—C42 | 1.371 (4) |
N4—H4 | 0.86 | C25—C54 | 1.384 (4) |
N5—C52 | 1.472 (3) | C25—C52 | 1.524 (3) |
N5—C38 | 1.327 (3) | C25—C49 | 1.380 (4) |
N6—C38 | 1.367 (3) | C33—C56 | 1.491 (4) |
N6—C33 | 1.396 (3) | C33—C37 | 1.337 (4) |
N5—H511 | 0.86 | C37—C53 | 1.464 (3) |
N6—H6 | 0.86 | C37—C52 | 1.517 (3) |
C9—C24 | 1.511 (3) | C42—C44 | 1.379 (4) |
C9—C18 | 1.525 (3) | C44—C49 | 1.378 (4) |
C18—C27 | 1.383 (4) | C60—C61 | 1.491 (4) |
C18—C43 | 1.386 (4) | C22—H22 | 0.93 |
C24—C30 | 1.351 (4) | C44—H44 | 0.93 |
C24—C41 | 1.464 (3) | C49—H49 | 0.93 |
C27—C36 | 1.376 (4) | C52—H52 | 0.98 |
C30—C59 | 1.492 (3) | C54—H54 | 0.93 |
C35—C36 | 1.384 (4) | C56—H56A | 0.96 |
C35—C51 | 1.369 (4) | C56—H56B | 0.96 |
C43—C51 | 1.382 (4) | C56—H56C | 0.96 |
C58—C63 | 1.451 (5) | C60—H60A | 0.97 |
C9—H9 | 0.98 | C60—H60B | 0.97 |
C27—H27 | 0.93 | C61—H61C | 0.96 |
C36—H36 | 0.93 | C61—H61A | 0.96 |
C43—H43 | 0.93 | C61—H61B | 0.96 |
C51—H51 | 0.93 | ||
O1···O14 | 2.657 (3) | C51···H54ii | 3.00 |
O2···C8i | 3.313 (3) | C53···H14Bviii | 3.06 (3) |
O2···O13 | 2.834 (3) | C53···H56C | 2.67 |
O2···O9ii | 3.225 (3) | C54···H39vii | 3.09 |
O2···N2iii | 2.882 (3) | C56···H60Axi | 3.06 |
O3···C59 | 2.834 (3) | C56···H15Ai | 3.08 (4) |
O3···O13iv | 2.789 (3) | C58···H13Aiv | 3.04 (3) |
O4···C18 | 3.068 (3) | C60···H14Bviii | 2.96 (4) |
O5···O13 | 2.633 (3) | H1···H14A | 2.36 |
O5···N1 | 32 (3) | H1···H36 | 2.30 |
O6···N6v | 2.862 (3) | H1···H511ii | 2.43 |
O6···O15 | 2.747 (3) | H1···H14B | 2.52 |
O6···C29v | 3.325 (3) | H1···O14 | 1.84 |
O7···C55 | 2.858 (3) | H2···O2iii | 2.05 |
O7···O15vi | 2.809 (3) | H2···H59B | 2.17 |
O8···C14 | 3.158 (3) | H2···C29iii | 2.94 |
O9···N3 | 3.079 (3) | H3···O9 | 2.25 |
O9···O2vii | 3.225 (3) | H3···H9A | 2.33 |
O9···O15 | 2.627 (3) | H4···O10v | 1.99 |
O10···O14vii | 2.752 (3) | H4···H55B | 2.32 |
O10···N4i | 2.854 (3) | H4···C38v | 2.88 |
O11···O14viii | 2.856 (3) | H5···H13B | 2.17 |
O11···C56 | 2.890 (3) | H5···H13A | 2.30 |
O12···C25 | 3.108 (3) | H5···O13 | 1.82 |
O13···O5 | 2.633 (3) | H5···H39 | 2.32 |
O13···O3vi | 2.789 (3) | H5···H11 | 2.26 |
O13···O2 | 2.834 (3) | H6···O6i | 2.05 |
O14···O11ix | 2.856 (3) | H6···H56B | 2.30 |
O14···C60ix | 3.273 (3) | H6···C8i | 2.93 |
O14···O10ii | 2.752 (3) | H9···O4 | 2.39 |
O14···O1 | 2.657 (3) | H9···H43 | 2.43 |
O15···C42 | 3.395 (4) | H9A···H44 | 2.33 |
O15···O9 | 2.627 (3) | H9A···H15A | 2.30 |
O15···C47iv | 3.392 (4) | H9A···H15B | 2.41 |
O15···C44 | 3.378 (4) | H9A···H3 | 2.33 |
O15···O6 | 2.747 (3) | H9A···O15 | 1.81 |
O15···O7iv | 2.809 (3) | H11···C31 | 3.03 |
O1···H511ii | 2.47 | H11···H5 | 2.26 |
O1···H56Av | 2.80 | H11···O5 | 2.14 |
O2···H13B | 2.02 (3) | H13A···O3vi | 1.91 (3) |
O2···H2iii | 2.05 | H13A···H5 | 2.30 |
O2···H59Biii | 2.83 | H13A···C58vi | 3.04 (3) |
O3···H13Aiv | 1.91 (3) | H13A···C41vi | 2.96 (3) |
O3···H58B | 2.57 | H13A···H58Bvi | 2.51 |
O3···H58A | 2.67 | H13B···O5 | 2.91 (4) |
O3···H59A | 2.25 | H13B···H5 | 2.17 |
O4···H9 | 2.39 | H13B···O2 | 2.02 (3) |
O5···H11 | 2.14 | H13B···H59Biii | 2.49 |
O5···H13B | 2.91 (4) | H13B···C29 | 2.93 (3) |
O5···H55Bi | 2.70 | H14A···C38ii | 2.79 (4) |
O6···H15A | 1.78 (4) | H14A···O10ii | 1.88 (4) |
O6···H6v | 2.05 | H14A···H1 | 2.36 |
O7···H15Bvi | 1.93 (3) | H14B···H1 | 2.52 |
O7···H55C | 2.22 | H14B···C60ix | 2.96 (4) |
O7···H47A | 2.55 | H14B···C53ix | 3.06 (3) |
O7···H47B | 2.68 | H14B···O11ix | 2.02 (3) |
O8···H34 | 2.38 | H14B···H60Bix | 2.52 |
O9···H3 | 2.25 | H15A···C8 | 2.75 (4) |
O10···H4i | 1.99 | H15A···C56v | 3.08 (4) |
O10···H14Avii | 1.88 (4) | H15A···H9A | 2.30 |
O11···H60B | 2.58 | H15A···O6 | 1.78 (4) |
O11···H14Bviii | 2.02 (3) | H15A···H56Bv | 2.59 |
O11···H60A | 2.64 | H15B···O7iv | 1.93 (3) |
O11···H56C | 2.18 | H15B···C17iv | 2.98 (3) |
O12···H52 | 2.35 | H15B···C47iv | 2.96 (3) |
O13···H58Bvi | 2.89 | H15B···H9A | 2.41 |
O13···H5 | 1.82 | H15B···H47Aiv | 2.42 |
O13···H39 | 2.82 | H26···C42 | 3.01 |
O14···H60Aix | 2.91 | H26···C36vii | 2.88 |
O14···H36 | 2.85 | H26···H34 | 2.42 |
O14···H1 | 1.84 | H26···C27vii | 3.03 |
O14···H60Bix | 2.75 | H26···H36vii | 2.54 |
O15···H59Cv | 2.89 | H27···H62Cii | 2.55 |
O15···H47Aiv | 2.75 | H27···C24 | 2.64 |
O15···H9A | 1.81 | H27···C30 | 3.01 |
O15···H44 | 2.76 | H34···H26 | 2.42 |
N1···O5 | 32 (3) | H34···O8 | 2.38 |
N2···O2iii | 2.882 (3) | H36···O14 | 2.85 |
N3···O9 | 3.079 (3) | H36···H26ii | 2.54 |
N4···O10v | 2.854 (3) | H36···H1 | 2.30 |
N6···O6i | 2.862 (3) | H36···C26ii | 2.97 |
C8···O2v | 3.313 (3) | H39···C54ii | 3.09 |
C8···C29v | 3.432 (4) | H39···O13 | 2.82 |
C14···O8 | 3.158 (3) | H39···C22ii | 3.04 |
C17···C48 | 3.574 (3) | H39···H5 | 2.32 |
C18···O4 | 3.068 (3) | H43···H44 | 2.58 |
C23···C48 | 3.466 (3) | H43···H9 | 2.43 |
C25···O12 | 3.108 (3) | H43···C44 | 3.08 |
C26···C36vii | 3.525 (4) | H43···C31 | 3.07 |
C26···C42 | 3.594 (3) | H44···C43 | 3.07 |
C27···C30 | 3.593 (4) | H44···O15 | 2.76 |
C27···C41 | 3.492 (4) | H44···H9A | 2.33 |
C29···O6i | 3.325 (3) | H44···H43 | 2.58 |
C29···C8i | 3.432 (4) | H47A···H15Bvi | 2.42 |
C30···C27 | 3.593 (4) | H47A···C44vi | 2.97 |
C33···C49 | 3.475 (4) | H47A···O7 | 2.55 |
C35···C54ii | 3.527 (3) | H47A···O15vi | 2.75 |
C36···C26ii | 3.525 (4) | H47B···O7 | 2.68 |
C39···C58vi | 3.556 (3) | H47B···H59Cxii | 2.50 |
C41···C27 | 3.492 (4) | H48···C32 | 2.64 |
C42···O15 | 3.395 (4) | H48···C23 | 2.86 |
C42···C26 | 3.594 (3) | H49···H63C | 2.59 |
C44···O15 | 3.378 (4) | H49···C37 | 2.64 |
C47···O15vi | 3.392 (4) | H49···C33 | 2.87 |
C48···C23 | 3.466 (3) | H52···H54 | 2.41 |
C48···C17 | 3.574 (3) | H52···O12 | 2.35 |
C49···C33 | 3.475 (4) | H54···C35vii | 3.04 |
C49···C53 | 3.565 (4) | H54···C51vii | 3.00 |
C53···C49 | 3.565 (4) | H54···H52 | 2.41 |
C54···C35vii | 3.527 (3) | H55A···H61Aii | 2.55 |
C55···O7 | 2.858 (3) | H55B···O5v | 2.70 |
C56···O11 | 2.890 (3) | H55B···H4 | 2.32 |
C58···C39iv | 3.556 (3) | H55C···C17 | 2.70 |
C59···O3 | 2.834 (3) | H55C···O7 | 2.22 |
C60···O14viii | 3.273 (3) | H56A···O1i | 2.80 |
C8···H15A | 2.75 (4) | H56A···H60Axi | 2.53 |
C8···H6v | 2.93 | H56B···C24 | 3.08 |
C17···H15Bvi | 2.98 (3) | H56B···H6 | 2.30 |
C17···H55C | 2.70 | H56B···C41 | 2.97 |
C22···H39vii | 3.04 | H56B···H15Ai | 2.59 |
C23···H48 | 2.86 | H56C···C53 | 2.67 |
C24···H27 | 2.64 | H56C···O11 | 2.18 |
C24···H56B | 3.08 | H58A···O3 | 2.67 |
C26···H36vii | 2.97 | H58B···H13Aiv | 2.51 |
C27···H62Cii | 3.03 | H58B···O13iv | 2.89 |
C27···H26ii | 3.03 | H58B···C39iv | 2.91 |
C29···H2iii | 2.94 | H58B···O3 | 2.57 |
C29···H13B | 2.93 (3) | H59A···C41 | 2.74 |
C30···H27 | 3.01 | H59A···O3 | 2.25 |
C31···H43 | 3.07 | H59B···H2 | 2.17 |
C31···H11 | 3.03 | H59B···H13Biii | 2.49 |
C32···H48 | 2.64 | H59B···O2iii | 2.83 |
C33···H49 | 2.87 | H59C···O15i | 2.89 |
C35···H61Bix | 3.09 | H59C···H47Bxiii | 2.50 |
C35···H54ii | 3.04 | H60A···O14viii | 2.91 |
C36···H26ii | 2.88 | H60A···O11 | 2.64 |
C36···H60Bix | 3.07 | H60A···H56Axi | 2.53 |
C37···H49 | 2.64 | H60A···C56xi | 3.06 |
C38···H4i | 2.88 | H60B···O14viii | 2.75 |
C38···H14Avii | 2.79 (4) | H60B···C36viii | 3.07 |
C38···H511x | 3.03 | H60B···O11 | 2.58 |
C39···H58Bvi | 2.91 | H60B···H14Bviii | 2.52 |
C39···H63Bvi | 3.03 | H61A···H55Avii | 2.55 |
C41···H59A | 2.74 | H61B···C35viii | 3.09 |
C41···H13Aiv | 2.96 (3) | H62B···C42vi | 3.09 |
C41···H62Cii | 3.04 | H62C···C27vii | 3.03 |
C41···H56B | 2.97 | H62C···H27vii | 2.55 |
C42···H62Biv | 3.09 | H62C···C41vii | 3.04 |
C42···H26 | 3.01 | H63B···C39iv | 3.03 |
C43···H44 | 3.07 | H63C···C49 | 3.04 |
C44···H47Aiv | 2.97 | H63C···H49 | 2.59 |
C44···H43 | 3.08 | H511···C38x | 3.03 |
C47···H15Bvi | 2.96 (3) | H511···O1vii | 2.47 |
C49···H63C | 3.04 | H511···H1vii | 2.43 |
C41—O4—C58 | 116.7 (2) | C39—C31—C57 | 119.6 (2) |
C35—O1—H1 | 109 | O5—C31—C57 | 118.1 (2) |
C17—O8—C47 | 116.56 (18) | C17—C32—C23 | 121.7 (2) |
C31—O5—H5 | 109 | C17—C32—C34 | 118.1 (2) |
C53—O12—C60 | 116.77 (18) | C23—C32—C34 | 120.0 (2) |
C42—O9—H9A | 109 | C14—C34—C32 | 113.26 (19) |
H13A—O13—H13B | 118 (3) | N3—C34—C32 | 108.97 (18) |
H14A—O14—H14B | 103 (4) | N3—C34—C14 | 110.25 (18) |
C9—N1—C29 | 126.0 (2) | C31—C39—C48 | 120.0 (2) |
C29—N2—C30 | 123.7 (2) | O8—C47—C62 | 108.1 (2) |
C29—N1—H11 | 117 | C14—C48—C39 | 121.1 (2) |
C9—N1—H11 | 117 | C26—C57—C31 | 120.0 (2) |
C29—N2—H2 | 118 | C14—C26—H26 | 119 |
C30—N2—H2 | 118 | C57—C26—H26 | 119 |
H15A—O15—H15B | 115 (3) | C14—C34—H34 | 108 |
C8—N3—C34 | 124.5 (2) | C32—C34—H34 | 108 |
C8—N4—C23 | 124.4 (2) | N3—C34—H34 | 108 |
C34—N3—H3 | 118 | C31—C39—H39 | 120 |
C8—N3—H3 | 118 | C48—C39—H39 | 120 |
C23—N4—H4 | 118 | O8—C47—H47A | 110 |
C8—N4—H4 | 118 | H47A—C47—H47B | 108 |
C38—N5—C52 | 125.1 (2) | C62—C47—H47A | 110 |
C33—N6—C38 | 124.2 (2) | C62—C47—H47B | 110 |
C52—N5—H511 | 117 | O8—C47—H47B | 110 |
C38—N5—H511 | 117 | C14—C48—H48 | 119 |
C38—N6—H6 | 118 | C39—C48—H48 | 119 |
C33—N6—H6 | 118 | H55A—C55—H55C | 109 |
C18—C9—C24 | 114.0 (2) | H55A—C55—H55B | 109 |
N1—C9—C18 | 110.38 (18) | C23—C55—H55A | 109 |
N1—C9—C24 | 109.13 (19) | C23—C55—H55B | 109 |
C9—C18—C27 | 122.5 (2) | H55B—C55—H55C | 109 |
C27—C18—C43 | 117.2 (2) | C23—C55—H55C | 109 |
C9—C18—C43 | 120.3 (2) | C26—C57—H57 | 120 |
C9—C24—C41 | 117.6 (2) | C31—C57—H57 | 120 |
C30—C24—C41 | 121.3 (2) | C47—C62—H62A | 109 |
C9—C24—C30 | 121.0 (2) | C47—C62—H62B | 109 |
C18—C27—C36 | 121.7 (2) | H62A—C62—H62C | 109 |
O2—C29—N2 | 120.5 (2) | H62A—C62—H62B | 109 |
N1—C29—N2 | 116.4 (2) | H62B—C62—H62C | 109 |
O2—C29—N1 | 123.2 (2) | C47—C62—H62C | 109 |
C24—C30—C59 | 127.5 (2) | C42—C22—C54 | 119.7 (3) |
N2—C30—C24 | 119.3 (2) | C52—C25—C54 | 119.9 (2) |
N2—C30—C59 | 113.2 (2) | C49—C25—C52 | 122.4 (2) |
C36—C35—C51 | 119.2 (2) | C49—C25—C54 | 117.6 (2) |
O1—C35—C36 | 122.1 (3) | N6—C33—C37 | 118.7 (2) |
O1—C35—C51 | 118.7 (2) | C37—C33—C56 | 129.0 (2) |
C27—C36—C35 | 120.1 (2) | N6—C33—C56 | 112.3 (2) |
O4—C41—C24 | 111.2 (2) | C33—C37—C52 | 120.4 (2) |
O3—C41—O4 | 121.9 (2) | C33—C37—C53 | 122.1 (2) |
O3—C41—C24 | 126.9 (3) | C52—C37—C53 | 117.3 (2) |
C18—C43—C51 | 121.6 (2) | O10—C38—N5 | 123.8 (2) |
C35—C51—C43 | 120.2 (2) | N5—C38—N6 | 115.6 (2) |
O4—C58—C63 | 108.7 (2) | O10—C38—N6 | 120.6 (2) |
N1—C9—H9 | 108 | O9—C42—C22 | 118.0 (2) |
C24—C9—H9 | 108 | O9—C42—C44 | 122.1 (3) |
C18—C9—H9 | 108 | C22—C42—C44 | 119.9 (2) |
C36—C27—H27 | 119 | C42—C44—C49 | 119.8 (2) |
C18—C27—H27 | 119 | C25—C49—C44 | 121.5 (2) |
C27—C36—H36 | 120 | N5—C52—C37 | 109.2 (2) |
C35—C36—H36 | 120 | N5—C52—C25 | 110.05 (19) |
C18—C43—H43 | 119 | C25—C52—C37 | 112.7 (2) |
C51—C43—H43 | 119 | O11—C53—O12 | 121.8 (2) |
C35—C51—H51 | 120 | O11—C53—C37 | 126.9 (3) |
C43—C51—H51 | 120 | O12—C53—C37 | 111.3 (2) |
C63—C58—H58A | 110 | C22—C54—C25 | 121.5 (2) |
O4—C58—H58B | 110 | O12—C60—C61 | 108.6 (2) |
C63—C58—H58B | 110 | C42—C22—H22 | 120 |
O4—C58—H58A | 110 | C54—C22—H22 | 120 |
H58A—C58—H58B | 108 | C42—C44—H44 | 120 |
H59A—C59—H59B | 109 | C49—C44—H44 | 120 |
C30—C59—H59C | 109 | C25—C49—H49 | 119 |
H59A—C59—H59C | 109 | C44—C49—H49 | 119 |
H59B—C59—H59C | 109 | C37—C52—H52 | 108 |
C30—C59—H59B | 110 | N5—C52—H52 | 108 |
C30—C59—H59A | 109 | C25—C52—H52 | 108 |
C58—C63—H63A | 109 | C22—C54—H54 | 119 |
C58—C63—H63C | 109 | C25—C54—H54 | 119 |
C58—C63—H63B | 110 | C33—C56—H56A | 109 |
H63B—C63—H63C | 109 | C33—C56—H56B | 109 |
H63A—C63—H63C | 109 | H56B—C56—H56C | 109 |
H63A—C63—H63B | 109 | H56A—C56—H56C | 109 |
O6—C8—N4 | 120.5 (2) | C33—C56—H56C | 109 |
O6—C8—N3 | 123.8 (2) | H56A—C56—H56B | 109 |
N3—C8—N4 | 115.7 (2) | O12—C60—H60A | 110 |
C34—C14—C48 | 122.4 (2) | O12—C60—H60B | 110 |
C26—C14—C34 | 119.9 (2) | C61—C60—H60A | 110 |
C26—C14—C48 | 117.7 (2) | C61—C60—H60B | 110 |
O7—C17—O8 | 121.6 (2) | H60A—C60—H60B | 108 |
O7—C17—C32 | 126.6 (2) | C60—C61—H61C | 109 |
O8—C17—C32 | 111.9 (2) | H61A—C61—H61C | 110 |
N4—C23—C55 | 112.9 (2) | H61B—C61—H61C | 109 |
N4—C23—C32 | 118.6 (2) | H61A—C61—H61B | 109 |
C32—C23—C55 | 128.5 (2) | C60—C61—H61A | 109 |
C14—C26—C57 | 121.6 (2) | C60—C61—H61B | 109 |
O5—C31—C39 | 122.3 (2) | ||
C58—O4—C41—O3 | 5.0 (4) | C36—C35—C51—C43 | 0.6 (4) |
C58—O4—C41—C24 | −175.9 (2) | C51—C35—C36—C27 | −0.4 (4) |
C41—O4—C58—C63 | 173.1 (2) | C18—C43—C51—C35 | −0.7 (4) |
C47—O8—C17—O7 | 2.6 (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—C62 | 173.3 (2) | C26—C14—C48—C39 | 1.5 (3) |
C60—O12—C53—O11 | 3.7 (4) | C34—C14—C48—C39 | 179.3 (2) |
C60—O12—C53—C37 | −174.8 (2) | C26—C14—C34—N3 | 85.8 (3) |
C53—O12—C60—C61 | 175.9 (2) | C26—C14—C34—C32 | −151.9 (2) |
C29—N1—C9—C18 | 104.2 (3) | C48—C14—C34—N3 | −92.0 (3) |
C9—N1—C29—O2 | −173.0 (2) | C48—C14—C34—C32 | 30.4 (3) |
C29—N1—C9—C24 | −21.8 (3) | O7—C17—C32—C34 | −172.9 (3) |
C9—N1—C29—N2 | 8.1 (4) | O8—C17—C32—C23 | −178.5 (2) |
C29—N2—C30—C59 | 165.2 (2) | O7—C17—C32—C23 | 1.4 (4) |
C30—N2—C29—N1 | 11.2 (3) | O8—C17—C32—C34 | 7.2 (3) |
C29—N2—C30—C24 | −13.1 (4) | C55—C23—C32—C17 | 1.0 (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—C34 | 175.2 (2) |
C34—N3—C8—N4 | 15.6 (3) | C14—C26—C57—C31 | 0.1 (4) |
C8—N3—C34—C14 | 93.8 (3) | O5—C31—C39—C48 | 179.4 (2) |
C23—N4—C8—N3 | 9.5 (3) | C39—C31—C57—C26 | 1.7 (4) |
C8—N4—C23—C32 | −14.6 (4) | C57—C31—C39—C48 | −1.9 (3) |
C8—N4—C23—C55 | 165.5 (2) | O5—C31—C57—C26 | −179.6 (2) |
C23—N4—C8—O6 | −168.8 (2) | C17—C32—C34—C14 | 75.7 (3) |
C38—N5—C52—C37 | −28.1 (3) | C23—C32—C34—N3 | 24.4 (3) |
C38—N5—C52—C25 | 96.2 (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—N6 | 12.9 (3) | C31—C39—C48—C14 | 0.3 (3) |
C38—N6—C33—C56 | 165.4 (2) | C54—C22—C42—O9 | −179.5 (2) |
C33—N6—C38—O10 | −168.1 (2) | C54—C22—C42—C44 | 2.0 (4) |
C33—N6—C38—N5 | 10.7 (3) | C42—C22—C54—C25 | −1.8 (4) |
C38—N6—C33—C37 | −14.9 (4) | C52—C25—C49—C44 | 178.3 (2) |
N1—C9—C24—C41 | −165.2 (2) | C54—C25—C49—C44 | 0.6 (3) |
C18—C9—C24—C30 | −105.1 (3) | C49—C25—C52—N5 | −90.3 (3) |
C18—C9—C24—C41 | 70.9 (3) | C49—C25—C52—C37 | 31.9 (3) |
C24—C9—C18—C27 | 28.6 (3) | C54—C25—C52—N5 | 87.3 (3) |
N1—C9—C18—C27 | −94.6 (3) | C54—C25—C52—C37 | −150.5 (2) |
N1—C9—C18—C43 | 85.2 (3) | C49—C25—C54—C22 | 0.5 (3) |
C24—C9—C18—C43 | −151.6 (2) | C52—C25—C54—C22 | −177.3 (2) |
N1—C9—C24—C30 | 18.8 (3) | N6—C33—C37—C52 | −3.9 (4) |
C9—C18—C27—C36 | 179.5 (2) | N6—C33—C37—C53 | −179.2 (2) |
C9—C18—C43—C51 | −179.3 (2) | C56—C33—C37—C52 | 175.8 (2) |
C43—C18—C27—C36 | −0.3 (3) | C56—C33—C37—C53 | 0.5 (4) |
C27—C18—C43—C51 | 0.5 (3) | C33—C37—C52—N5 | 22.4 (3) |
C9—C24—C41—O3 | −172.6 (3) | C33—C37—C52—C25 | −100.2 (3) |
C9—C24—C41—O4 | 8.3 (3) | C53—C37—C52—N5 | −162.1 (2) |
C41—C24—C30—N2 | −179.6 (2) | C53—C37—C52—C25 | 75.3 (3) |
C41—C24—C30—C59 | 2.3 (4) | C33—C37—C53—O11 | 3.9 (4) |
C9—C24—C30—C59 | 178.2 (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—O12 | 6.9 (3) |
C30—C24—C41—O3 | 3.4 (4) | O9—C42—C44—C49 | −179.5 (2) |
C18—C27—C36—C35 | 0.2 (4) | C22—C42—C44—C49 | −1.0 (4) |
O1—C35—C51—C43 | 179.3 (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. |
D—H···A | D—H | H···A | D···A | D—H···A |
N1—H11···O5 | 0.86 | 2.14 | 3.002 (3) | 176 |
N2—H2···O2iii | 0.86 | 2.05 | 2.882 (3) | 162 |
N3—H3···O9 | 0.86 | 2.25 | 3.079 (3) | 161 |
N4—H4···O10v | 0.86 | 1.99 | 2.854 (3) | 177 |
N5—H511···O1vii | 0.86 | 2.47 | 3.278 (3) | 158 |
N6—H6···O6i | 0.86 | 2.05 | 2.862 (3) | 157 |
O1—H1···O14 | 0.82 | 1.84 | 2.657 (3) | 171 |
O5—H5···O13 | 0.82 | 1.82 | 2.633 (3) | 172 |
O9—H9A···O15 | 0.82 | 1.81 | 2.627 (3) | 174 |
O13—H13A···O3vi | 0.89 (3) | 1.91 (3) | 2.789 (3) | 172 (3) |
O13—H13B···O2 | 0.86 (3) | 2.02 (3) | 2.834 (3) | 158 (3) |
O14—H14A···O10ii | 0.93 (4) | 1.88 (4) | 2.752 (3) | 156 (4) |
O14—H14B···O11ix | 0.86 (3) | 2.02 (3) | 2.856 (3) | 164 (3) |
O15—H15A···O6 | 1.03 (4) | 1.78 (4) | 2.747 (3) | 155 (3) |
O15—H15B···O7iv | 0.88 (3) | 1.93 (3) | 2.809 (3) | 173 (3) |
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; (ix) −x, y+1/2, −z+1/2. |
Experimental details
Crystal data | |
Chemical formula | C14H16N2O4·H2O |
Mr | 294.30 |
Crystal system, space group | Monoclinic, P21/c |
Temperature (K) | 292 |
a, b, c (Å) | 11.1583 (15), 17.773 (2), 21.686 (3) |
β (°) | 91.448 (2) |
V (Å3) | 4299.3 (10) |
Z | 12 |
Radiation type | Mo Kα |
µ (mm−1) | 0.10 |
Crystal size (mm) | 0.50 × 0.20 × 0.10 |
Data collection | |
Diffractometer | Bruker SMART APEX CCD diffractometer |
Absorption correction | Multi-scan (SADABS; Sheldrick, 1996) |
Tmin, Tmax | 0.906, 0.990 |
No. of measured, independent and observed [I > 2σ(I)] reflections | 33204, 8419, 3947 |
Rint | 0.083 |
(sin θ/λ)max (Å−1) | 0.617 |
Refinement | |
R[F2 > 2σ(F2)], wR(F2), S | 0.054, 0.138, 0.90 |
No. of reflections | 8419 |
No. of parameters | 601 |
H-atom treatment | H atoms treated by a mixture of independent and constrained refinement |
Δρmax, Δρmin (e Å−3) | 0.19, −0.23 |
Computer programs: SMART (Bruker, 2004), SAINT (Bruker, 2004), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), ORTEP-3 for Windows (Farrugia, 1999) and CAMERON (Watkin et al., 1993), PLATON (Spek, 2003).
D—H···A | D—H | H···A | D···A | D—H···A |
N1—H11···O5 | 0.86 | 2.14 | 3.002 (3) | 176 |
N2—H2···O2i | 0.86 | 2.05 | 2.882 (3) | 162 |
N3—H3···O9 | 0.86 | 2.25 | 3.079 (3) | 161 |
N4—H4···O10ii | 0.86 | 1.99 | 2.854 (3) | 177 |
N5—H511···O1iii | 0.86 | 2.47 | 3.278 (3) | 158 |
N6—H6···O6iv | 0.86 | 2.05 | 2.862 (3) | 157 |
O1—H1···O14 | 0.82 | 1.84 | 2.657 (3) | 171 |
O5—H5···O13 | 0.82 | 1.82 | 2.633 (3) | 172 |
O9—H9A···O15 | 0.82 | 1.81 | 2.627 (3) | 174 |
O13—H13A···O3v | 0.89 (3) | 1.91 (3) | 2.789 (3) | 172 (3) |
O13—H13B···O2 | 0.86 (3) | 2.02 (3) | 2.834 (3) | 158 (3) |
O14—H14A···O10vi | 0.93 (4) | 1.88 (4) | 2.752 (3) | 156 (4) |
O14—H14B···O11vii | 0.86 (3) | 2.02 (3) | 2.856 (3) | 164 (3) |
O15—H15A···O6 | 1.03 (4) | 1.78 (4) | 2.747 (3) | 155 (3) |
O15—H15B···O7viii | 0.88 (3) | 1.93 (3) | 2.809 (3) | 173 (3) |
Symmetry codes: (i) −x+1, −y+1, −z+1; (ii) x, −y+1/2, z−1/2; (iii) −x+1, y−1/2, −z+1/2; (iv) x, −y+1/2, z+1/2; (v) x+1, y, z; (vi) −x+1, y+1/2, −z+1/2; (vii) −x, y+1/2, −z+1/2; (viii) x−1, y, z. |
Acknowledgements
We thank the Department of Science and Technology, India, for use of the CCD facility set up under the IRHPA–DST program at IISc.
References
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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.