organic compounds
1-(Pyridin-2-yl)-2,4-bis[(pyridin-2-yl)carbonyl]-3,5-bis(3,4,5-trimethoxyphenyl)cyclohexanol 2.25-hydrate
aPG and Research Department of Physics, Queen Mary's College, Chennai-4, Tamilnadu, India, bPG Department of Physics, Bhaktavatsalam Memorial College for Women, Chennai-80, Tamilnadu, India, and cDepartment of Physics, Bharathi Women's College, Chennai-108, Tamilnadu, India
*Correspondence e-mail: guqmc@yahoo.com
In the title compound, C41H41N3O9·2.25H2O, the cyclohexanol ring adopts a chair conformation. The cyclohexanol ring makes dihedral angles of 87.89 (7) and 75.53 (8)° with the mean planes of the trimethoxyphenyl rings and dihedral angles of 84.18 (8), 85.07 (7) and 82.03 (8)° with the pyridine rings. In the crystal, the packing is stabilized by C—H⋯O, O—H⋯O and O—H⋯N hydrogen bonds involving water molecules and methoxy O atoms, resulting in a supramolecular network. One of the methoxy groups is disordered over two sets of sites with occupancy factors of 0.63 (3) and 0.37 (3).
CCDC reference: 1568420
Structure description
The title compound (Fig. 1) has a central cyclohexanol ring attached to two trimethoxyphenyl, one pyridine and two pyridinecarbonyl rings. The dihedral angle between the trimethoxyphenyl rings E and F is 69.65 (7)°. The cyclohexanol ring A (C39–C44) makes dihedral angles of 75.53 (8) and 87.89 (7)°, respectively, with the mean planes of the rings E (C10–C15) and F (C1–C6). The pyridine rings B (N2/C20–C24), C (N1/C25–C29) and D (N1/C25–C29) are inclined to the central cyclohexanol ring by dihedral angles of 85.07 (7), 82.03 (8) and 84.18 (8)°, respectively. The cyclohexanol ring A adopts a chair conformation with puckering parameters q2 = 0.034 (2), q3 = 0.595 (2) and QT = 0.597 (2) Å, φ2 = 288 (4) and θ2 = 3.81 (19)°, and is similar to that observed in reported structures (Çelik et al., 2016; Fun et al., 2012).
In the crystal, the molecules are linked by C—H⋯O, O—H⋯O and O—H⋯N hydrogen bonds (Fig. 2, Table 1). The trifurcated atom O10 (acting as donor to two hydrogen bonds and acceptor to one) and bifurcated atom O11 (acting as acceptor to two hydrogen bonds) of the water molecules are actively involved in the formation of hydrogen bonds through carbonyl O and pyridine N atoms. The O9 atom from the hydroxyl group generates intra- and intermolecular interactions with ketone atoms through O9—H9⋯O8 and O9—H9⋯O7 bonds. The packing of the molecules viewed along the a axis is shown in Fig. 3.
Synthesis and crystallization
The title compound was synthesized by the following Claisen–Schmidt reaction. In this procedure, 4-acetylpyridine(1.5 ml, 0.01 mol) and 3,4,5-trimethoxybenzaldehyde (2.6 g, 0.01 mol) were dissolved in 50 ml of ethanol in a round-bottomed flask. After 15 minutes, NaOH (10%) was added and the reaction mixture was maintained at 283 K and stirred for 5 h. Then the mixture was poured onto ice. The white-coloured precipitate was collected and washed with distilled water. A colourless, diffraction-quality crystal was obtained from repeated recrystallization from ethanol solution (yield: 87%, m.p. 398 K).
Refinement
Crystal data, data collection and structure . Atom C7 and its attached H atoms are disordered over two sets of sites with occupancy factors of 0.63 (3) and 0.37 (3). Atom O12 was refined with a fixed occupancy factor of 0.25 and no H atoms attached.
details are summarized in Table 2
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Structural data
CCDC reference: 1568420
https://doi.org/10.1107/S2414314617016248/hg4029sup1.cif
contains datablock I. DOI:Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S2414314617016248/hg4029Isup2.hkl
Supporting information file. DOI: https://doi.org/10.1107/S2414314617016248/hg4029Isup3.cml
Data collection: APEX2 (Bruker, 2004); cell
APEX2 and SAINT (Bruker, 2004); data reduction: SAINT and XPREP (Bruker, 2004); program(s) used to solve structure: SIR92 (Altomare et al., 1993); program(s) used to refine structure: SHELXL2014 (Sheldrick, 2015); molecular graphics: ORTEP-3 for Windows (Farrugia, 2012) and Mercury (Macrae et al., 2008); software used to prepare material for publication: SHELXL2014 (Sheldrick, 2015).4C41H41N3O9·9H2O | F(000) = 1608 |
Mr = 3039.20 | Dx = 1.270 Mg m−3 |
Monoclinic, P21/n | Mo Kα radiation, λ = 0.71073 Å |
a = 15.2367 (10) Å | Cell parameters from 7551 reflections |
b = 14.8923 (7) Å | θ = 2.5–21.9° |
c = 18.8149 (9) Å | µ = 0.09 mm−1 |
β = 111.474 (2)° | T = 293 K |
V = 3972.9 (4) Å3 | Block, colourless |
Z = 1 | 0.30 × 0.25 × 0.20 mm |
Bruker Kappa APEXII CCD diffractometer | 6999 independent reflections |
Radiation source: fine-focus sealed tube | 4142 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.042 |
ω and φ scan | θmax = 25.0°, θmin = 2.2° |
Absorption correction: multi-scan (SADABS; Bruker, 2004) | h = −15→18 |
Tmin = 0.972, Tmax = 0.982 | k = −17→17 |
38138 measured reflections | l = −22→22 |
Refinement on F2 | 13 restraints |
Least-squares matrix: full | Hydrogen site location: mixed |
R[F2 > 2σ(F2)] = 0.047 | H atoms treated by a mixture of independent and constrained refinement |
wR(F2) = 0.130 | w = 1/[σ2(Fo2) + (0.0408P)2 + 2.0333P] where P = (Fo2 + 2Fc2)/3 |
S = 1.08 | (Δ/σ)max < 0.001 |
6995 reflections | Δρmax = 0.18 e Å−3 |
533 parameters | Δρmin = −0.20 e Å−3 |
Refinement. H atoms were positioned geometrically and treated as riding on their parent atoms and refined with, C—H = 0.93–0.96 Å and O—H = 0.82 Å, with Uiso(H) = 1.5 Ueq(c-methyl) and Uiso(H) = 1.2Ueq(O) for other H atoms. The water H atoms were identified through Fourier maps and fixed with their parent O atoms using DFIX 0.82 (2). |
x | y | z | Uiso*/Ueq | Occ. (<1) | |
C1 | 0.47583 (16) | 0.04020 (14) | 0.68518 (13) | 0.0309 (5) | |
C2 | 0.43319 (18) | 0.02820 (16) | 0.73806 (13) | 0.0393 (6) | |
H2 | 0.3882 | −0.0166 | 0.7308 | 0.047* | |
C3 | 0.4578 (2) | 0.08296 (18) | 0.80163 (14) | 0.0463 (7) | |
C4 | 0.5238 (2) | 0.15036 (18) | 0.81334 (15) | 0.0519 (7) | |
C5 | 0.5690 (2) | 0.15985 (17) | 0.76169 (16) | 0.0503 (7) | |
C6 | 0.54417 (18) | 0.10571 (16) | 0.69746 (14) | 0.0402 (6) | |
H6 | 0.5736 | 0.1135 | 0.6624 | 0.048* | |
C7 | 0.456 (2) | 0.019 (2) | 0.9148 (13) | 0.113 (7) | 0.37 (3) |
H7A | 0.4212 | 0.0208 | 0.9481 | 0.170* | 0.37 (3) |
H7B | 0.5199 | 0.0377 | 0.9421 | 0.170* | 0.37 (3) |
H7C | 0.4563 | −0.0417 | 0.8969 | 0.170* | 0.37 (3) |
C7' | 0.4051 (13) | −0.0152 (6) | 0.8755 (10) | 0.091 (4) | 0.63 (3) |
H7'1 | 0.4635 | −0.0470 | 0.8872 | 0.136* | 0.63 (3) |
H7'2 | 0.3568 | −0.0442 | 0.8337 | 0.136* | 0.63 (3) |
H7'3 | 0.3873 | −0.0152 | 0.9195 | 0.136* | 0.63 (3) |
C8 | 0.5355 (4) | 0.2949 (3) | 0.8708 (3) | 0.1271 (18) | |
H8A | 0.4757 | 0.3078 | 0.8314 | 0.191* | |
H8B | 0.5851 | 0.3203 | 0.8572 | 0.191* | |
H8C | 0.5372 | 0.3206 | 0.9181 | 0.191* | |
C9 | 0.7029 (3) | 0.2193 (3) | 0.7414 (2) | 0.0899 (12) | |
H9A | 0.7302 | 0.1603 | 0.7483 | 0.135* | |
H9B | 0.7517 | 0.2631 | 0.7629 | 0.135* | |
H9C | 0.6714 | 0.2309 | 0.6878 | 0.135* | |
C10 | 0.48096 (18) | −0.27134 (15) | 0.58138 (13) | 0.0354 (6) | |
C11 | 0.56584 (19) | −0.30086 (16) | 0.57766 (14) | 0.0424 (6) | |
H11 | 0.6017 | −0.2624 | 0.5602 | 0.051* | |
C12 | 0.5971 (2) | −0.38757 (17) | 0.59992 (15) | 0.0466 (7) | |
C13 | 0.5450 (2) | −0.44482 (16) | 0.62708 (14) | 0.0462 (7) | |
C14 | 0.4599 (2) | −0.41605 (17) | 0.62933 (14) | 0.0453 (7) | |
C15 | 0.42774 (19) | −0.32902 (16) | 0.60684 (14) | 0.0424 (6) | |
H15 | 0.3707 | −0.3099 | 0.6090 | 0.051* | |
C16 | 0.3273 (3) | −0.4507 (3) | 0.6625 (3) | 0.1220 (18) | |
H16A | 0.3383 | −0.3976 | 0.6935 | 0.183* | |
H16B | 0.3047 | −0.4978 | 0.6861 | 0.183* | |
H16C | 0.2811 | −0.4381 | 0.6129 | 0.183* | |
C17 | 0.5445 (3) | −0.5983 (2) | 0.6001 (2) | 0.0919 (13) | |
H17A | 0.4768 | −0.5969 | 0.5807 | 0.138* | |
H17B | 0.5661 | −0.6552 | 0.6240 | 0.138* | |
H17C | 0.5664 | −0.5899 | 0.5587 | 0.138* | |
C18 | 0.7276 (2) | −0.3747 (2) | 0.5590 (2) | 0.0798 (10) | |
H18A | 0.6883 | −0.3698 | 0.5060 | 0.120* | |
H18B | 0.7846 | −0.4060 | 0.5638 | 0.120* | |
H18C | 0.7429 | −0.3158 | 0.5807 | 0.120* | |
C19 | 0.32405 (17) | 0.09088 (16) | 0.54529 (13) | 0.0354 (6) | |
C20 | 0.28709 (19) | 0.14740 (16) | 0.59363 (14) | 0.0426 (7) | |
C21 | 0.3261 (3) | 0.23114 (19) | 0.61551 (18) | 0.0694 (9) | |
H21 | 0.3738 | 0.2524 | 0.6002 | 0.083* | |
C22 | 0.2919 (4) | 0.2829 (2) | 0.6613 (2) | 0.0973 (14) | |
H22 | 0.3200 | 0.3384 | 0.6781 | 0.117* | |
N2 | 0.2214 (3) | 0.2575 (3) | 0.68226 (19) | 0.0988 (12) | |
C23 | 0.1847 (3) | 0.1778 (3) | 0.6599 (2) | 0.0857 (11) | |
H23 | 0.1349 | 0.1593 | 0.6737 | 0.103* | |
C24 | 0.2162 (2) | 0.1203 (2) | 0.61726 (16) | 0.0599 (8) | |
H24 | 0.1896 | 0.0636 | 0.6045 | 0.072* | |
C25 | 0.21191 (18) | −0.05937 (15) | 0.44586 (13) | 0.0360 (6) | |
C26 | 0.1745 (2) | −0.03033 (18) | 0.37130 (14) | 0.0513 (7) | |
H26 | 0.2139 | −0.0160 | 0.3451 | 0.062* | |
C27 | 0.0774 (3) | −0.0226 (2) | 0.33555 (18) | 0.0712 (10) | |
H27 | 0.0537 | −0.0032 | 0.2851 | 0.085* | |
N1 | 0.01609 (19) | −0.04114 (19) | 0.36869 (16) | 0.0731 (8) | |
C28 | 0.0532 (2) | −0.0694 (2) | 0.44029 (18) | 0.0602 (8) | |
H28 | 0.0121 | −0.0832 | 0.4651 | 0.072* | |
C29 | 0.14823 (18) | −0.07962 (17) | 0.48042 (15) | 0.0457 (7) | |
H29 | 0.1697 | −0.1001 | 0.5306 | 0.055* | |
C30 | 0.57500 (18) | −0.12177 (15) | 0.68717 (13) | 0.0332 (6) | |
C31 | 0.59889 (17) | −0.14134 (15) | 0.77039 (13) | 0.0354 (6) | |
C32 | 0.67705 (19) | −0.10218 (18) | 0.82379 (14) | 0.0481 (7) | |
H32 | 0.7160 | −0.0650 | 0.8086 | 0.058* | |
C33 | 0.6968 (2) | −0.1188 (2) | 0.90010 (16) | 0.0590 (8) | |
H33 | 0.7498 | −0.0917 | 0.9355 | 0.071* | |
N3 | 0.64484 (19) | −0.17117 (17) | 0.92603 (13) | 0.0616 (7) | |
C34 | 0.5709 (2) | −0.2095 (2) | 0.87408 (17) | 0.0668 (9) | |
H34 | 0.5343 | −0.2477 | 0.8909 | 0.080* | |
C35 | 0.5443 (2) | −0.19640 (18) | 0.79624 (15) | 0.0541 (8) | |
H35 | 0.4908 | −0.2242 | 0.7621 | 0.065* | |
C39 | 0.44920 (16) | −0.01741 (14) | 0.61395 (12) | 0.0284 (5) | |
H39 | 0.4867 | 0.0027 | 0.5843 | 0.034* | |
C40 | 0.34386 (16) | −0.00810 (14) | 0.56285 (12) | 0.0294 (5) | |
H40 | 0.3061 | −0.0285 | 0.5922 | 0.035* | |
C41 | 0.31782 (16) | −0.06659 (14) | 0.48983 (12) | 0.0310 (5) | |
C42 | 0.34647 (17) | −0.16422 (15) | 0.51199 (13) | 0.0346 (6) | |
H42A | 0.3326 | −0.1996 | 0.4659 | 0.042* | |
H42B | 0.3090 | −0.1879 | 0.5397 | 0.042* | |
C43 | 0.45134 (16) | −0.17447 (14) | 0.56144 (12) | 0.0322 (6) | |
H43 | 0.4883 | −0.1501 | 0.5328 | 0.039* | |
C44 | 0.47249 (16) | −0.11756 (14) | 0.63428 (12) | 0.0302 (5) | |
H44 | 0.4332 | −0.1393 | 0.6619 | 0.036* | |
O1 | 0.41605 (17) | 0.07301 (15) | 0.85542 (12) | 0.0709 (6) | |
O2 | 0.54795 (17) | 0.20044 (15) | 0.87925 (12) | 0.0811 (7) | |
O3 | 0.63731 (17) | 0.22451 (15) | 0.77829 (13) | 0.0807 (7) | |
O4 | 0.41173 (16) | −0.47771 (12) | 0.65519 (12) | 0.0662 (6) | |
O5 | 0.58008 (15) | −0.52884 (11) | 0.65415 (11) | 0.0642 (6) | |
O6 | 0.67918 (16) | −0.42277 (13) | 0.59817 (13) | 0.0700 (6) | |
O7 | 0.63819 (12) | −0.10414 (11) | 0.66429 (9) | 0.0445 (4) | |
O8 | 0.34263 (16) | 0.12696 (11) | 0.49476 (11) | 0.0609 (6) | |
O9 | 0.36986 (11) | −0.04089 (10) | 0.44406 (8) | 0.0382 (4) | |
H9 | 0.3575 | 0.0113 | 0.4302 | 0.057* | |
O10 | 0.6558 (3) | −0.2192 (2) | 1.07603 (16) | 0.1056 (10) | |
O11 | 0.2246 (2) | 0.3390 (2) | 0.82088 (18) | 0.1155 (11) | |
O12 | 0.3307 (11) | −0.5495 (10) | 0.7994 (8) | 0.149 (5)* | 0.25 |
H11B | 0.219 (3) | 0.321 (2) | 0.7766 (11) | 0.125 (16)* | |
H11A | 0.257 (2) | 0.2982 (18) | 0.8533 (14) | 0.082 (13)* | |
H10A | 0.651 (3) | −0.202 (3) | 1.0309 (15) | 0.16 (2)* | |
H10B | 0.617 (3) | −0.188 (3) | 1.089 (2) | 0.16 (2)* |
U11 | U22 | U33 | U12 | U13 | U23 | |
C1 | 0.0301 (14) | 0.0274 (12) | 0.0343 (13) | 0.0018 (11) | 0.0106 (11) | −0.0024 (10) |
C2 | 0.0418 (16) | 0.0362 (14) | 0.0405 (14) | −0.0055 (12) | 0.0159 (12) | −0.0059 (11) |
C3 | 0.0505 (18) | 0.0501 (16) | 0.0425 (15) | 0.0010 (14) | 0.0221 (13) | −0.0081 (13) |
C4 | 0.0568 (19) | 0.0496 (17) | 0.0471 (16) | −0.0063 (15) | 0.0166 (15) | −0.0206 (14) |
C5 | 0.0495 (18) | 0.0410 (15) | 0.0570 (17) | −0.0149 (14) | 0.0155 (15) | −0.0133 (14) |
C6 | 0.0425 (16) | 0.0384 (14) | 0.0414 (14) | −0.0050 (12) | 0.0174 (12) | −0.0046 (12) |
C7 | 0.117 (14) | 0.153 (17) | 0.076 (10) | 0.041 (12) | 0.041 (10) | 0.031 (12) |
C7' | 0.120 (10) | 0.091 (6) | 0.093 (8) | 0.019 (5) | 0.078 (7) | 0.024 (5) |
C8 | 0.176 (5) | 0.070 (3) | 0.153 (4) | −0.023 (3) | 0.081 (4) | −0.065 (3) |
C9 | 0.080 (3) | 0.108 (3) | 0.078 (2) | −0.055 (2) | 0.024 (2) | −0.008 (2) |
C10 | 0.0428 (16) | 0.0270 (13) | 0.0323 (13) | 0.0017 (12) | 0.0090 (11) | −0.0036 (10) |
C11 | 0.0492 (18) | 0.0316 (14) | 0.0450 (15) | 0.0028 (12) | 0.0155 (13) | −0.0015 (11) |
C12 | 0.0476 (18) | 0.0393 (15) | 0.0483 (16) | 0.0112 (14) | 0.0119 (14) | −0.0007 (13) |
C13 | 0.0540 (19) | 0.0300 (14) | 0.0437 (15) | 0.0082 (13) | 0.0052 (14) | 0.0013 (12) |
C14 | 0.0536 (19) | 0.0338 (14) | 0.0427 (15) | −0.0034 (14) | 0.0108 (13) | 0.0016 (12) |
C15 | 0.0445 (17) | 0.0330 (14) | 0.0446 (15) | 0.0048 (12) | 0.0104 (13) | 0.0003 (12) |
C16 | 0.114 (4) | 0.070 (3) | 0.218 (5) | 0.007 (3) | 0.103 (4) | 0.046 (3) |
C17 | 0.098 (3) | 0.0373 (18) | 0.118 (3) | 0.0069 (18) | 0.012 (2) | −0.0150 (19) |
C18 | 0.064 (2) | 0.081 (2) | 0.102 (3) | 0.0197 (19) | 0.040 (2) | 0.008 (2) |
C19 | 0.0358 (15) | 0.0360 (14) | 0.0352 (14) | 0.0016 (11) | 0.0137 (12) | −0.0010 (11) |
C20 | 0.0503 (18) | 0.0368 (15) | 0.0420 (15) | 0.0114 (13) | 0.0184 (13) | 0.0033 (12) |
C21 | 0.097 (3) | 0.0397 (17) | 0.080 (2) | 0.0060 (17) | 0.042 (2) | −0.0069 (16) |
C22 | 0.137 (4) | 0.051 (2) | 0.102 (3) | 0.016 (2) | 0.041 (3) | −0.023 (2) |
N2 | 0.120 (3) | 0.104 (3) | 0.083 (2) | 0.040 (2) | 0.049 (2) | −0.016 (2) |
C23 | 0.081 (3) | 0.105 (3) | 0.083 (3) | 0.031 (2) | 0.044 (2) | −0.009 (2) |
C24 | 0.053 (2) | 0.068 (2) | 0.0656 (19) | 0.0098 (16) | 0.0309 (17) | −0.0069 (16) |
C25 | 0.0397 (16) | 0.0300 (13) | 0.0355 (13) | 0.0021 (11) | 0.0103 (12) | −0.0025 (11) |
C26 | 0.0461 (19) | 0.0629 (18) | 0.0377 (15) | 0.0048 (14) | 0.0068 (14) | 0.0035 (13) |
C27 | 0.065 (3) | 0.081 (2) | 0.0473 (18) | 0.0097 (19) | −0.0024 (18) | 0.0069 (16) |
N1 | 0.0465 (17) | 0.088 (2) | 0.0683 (19) | 0.0058 (15) | 0.0021 (15) | −0.0030 (15) |
C28 | 0.0429 (19) | 0.069 (2) | 0.065 (2) | −0.0062 (15) | 0.0156 (16) | −0.0116 (16) |
C29 | 0.0373 (17) | 0.0508 (16) | 0.0438 (15) | −0.0030 (13) | 0.0085 (13) | −0.0009 (13) |
C30 | 0.0390 (16) | 0.0264 (12) | 0.0327 (13) | 0.0021 (11) | 0.0113 (12) | −0.0001 (10) |
C31 | 0.0369 (15) | 0.0321 (13) | 0.0336 (13) | 0.0025 (11) | 0.0086 (12) | 0.0034 (11) |
C32 | 0.0464 (18) | 0.0527 (17) | 0.0415 (15) | −0.0063 (14) | 0.0114 (13) | 0.0014 (13) |
C33 | 0.061 (2) | 0.066 (2) | 0.0405 (16) | −0.0066 (16) | 0.0071 (15) | −0.0051 (15) |
N3 | 0.0672 (19) | 0.0712 (17) | 0.0400 (14) | 0.0056 (15) | 0.0121 (13) | 0.0119 (13) |
C34 | 0.071 (2) | 0.074 (2) | 0.0531 (19) | −0.0096 (18) | 0.0193 (18) | 0.0245 (17) |
C35 | 0.0544 (19) | 0.0562 (17) | 0.0420 (16) | −0.0145 (15) | 0.0063 (14) | 0.0118 (13) |
C39 | 0.0298 (14) | 0.0268 (12) | 0.0295 (12) | −0.0002 (10) | 0.0121 (10) | 0.0004 (10) |
C40 | 0.0338 (14) | 0.0273 (12) | 0.0301 (12) | 0.0010 (10) | 0.0155 (11) | 0.0016 (10) |
C41 | 0.0353 (15) | 0.0317 (13) | 0.0267 (12) | 0.0010 (11) | 0.0121 (11) | 0.0018 (10) |
C42 | 0.0413 (16) | 0.0303 (13) | 0.0306 (12) | 0.0005 (11) | 0.0112 (11) | −0.0032 (10) |
C43 | 0.0387 (15) | 0.0262 (12) | 0.0312 (12) | 0.0016 (11) | 0.0122 (11) | −0.0005 (10) |
C44 | 0.0337 (14) | 0.0266 (12) | 0.0308 (12) | 0.0006 (10) | 0.0125 (11) | 0.0008 (10) |
O1 | 0.0972 (18) | 0.0766 (15) | 0.0572 (13) | −0.0113 (13) | 0.0500 (13) | −0.0206 (12) |
O2 | 0.1008 (19) | 0.0757 (16) | 0.0674 (14) | −0.0199 (13) | 0.0314 (13) | −0.0427 (12) |
O3 | 0.0823 (17) | 0.0742 (15) | 0.0899 (16) | −0.0475 (13) | 0.0366 (14) | −0.0343 (13) |
O4 | 0.0750 (16) | 0.0400 (11) | 0.0843 (15) | 0.0002 (11) | 0.0298 (13) | 0.0160 (10) |
O5 | 0.0787 (15) | 0.0327 (10) | 0.0642 (13) | 0.0145 (10) | 0.0059 (11) | 0.0074 (9) |
O6 | 0.0645 (15) | 0.0540 (12) | 0.0939 (16) | 0.0241 (11) | 0.0319 (13) | 0.0107 (11) |
O7 | 0.0390 (11) | 0.0520 (11) | 0.0433 (10) | 0.0027 (9) | 0.0160 (9) | 0.0043 (8) |
O8 | 0.1010 (17) | 0.0377 (10) | 0.0628 (12) | 0.0081 (10) | 0.0523 (12) | 0.0098 (9) |
O9 | 0.0454 (11) | 0.0391 (9) | 0.0359 (9) | 0.0048 (8) | 0.0217 (8) | 0.0044 (7) |
O10 | 0.161 (3) | 0.105 (2) | 0.0690 (18) | 0.051 (2) | 0.0637 (19) | 0.0157 (15) |
O11 | 0.127 (3) | 0.152 (3) | 0.0771 (19) | 0.063 (2) | 0.0488 (19) | −0.011 (2) |
C1—C6 | 1.383 (3) | C19—C40 | 1.517 (3) |
C1—C2 | 1.385 (3) | C20—C24 | 1.371 (4) |
C1—C39 | 1.516 (3) | C20—C21 | 1.378 (4) |
C2—C3 | 1.381 (3) | C21—C22 | 1.392 (5) |
C2—H2 | 0.9300 | C21—H21 | 0.9300 |
C3—C4 | 1.380 (4) | C22—N2 | 1.328 (5) |
C3—O1 | 1.386 (3) | C22—H22 | 0.9300 |
C4—O2 | 1.377 (3) | N2—C23 | 1.314 (5) |
C4—C5 | 1.389 (4) | C23—C24 | 1.374 (4) |
C5—O3 | 1.368 (3) | C23—H23 | 0.9300 |
C5—C6 | 1.385 (3) | C24—H24 | 0.9300 |
C6—H6 | 0.9300 | C25—C26 | 1.376 (3) |
C7—O1 | 1.333 (11) | C25—C29 | 1.385 (3) |
C7—H7A | 0.9600 | C25—C41 | 1.524 (3) |
C7—H7B | 0.9600 | C26—C27 | 1.387 (4) |
C7—H7C | 0.9600 | C26—H26 | 0.9300 |
C7'—O1 | 1.394 (7) | C27—N1 | 1.329 (4) |
C7'—H7'1 | 0.9600 | C27—H27 | 0.9300 |
C7'—H7'2 | 0.9600 | N1—C28 | 1.324 (4) |
C7'—H7'3 | 0.9600 | C28—C29 | 1.375 (4) |
C8—O2 | 1.421 (4) | C28—H28 | 0.9300 |
C8—H8A | 0.9600 | C29—H29 | 0.9300 |
C8—H8B | 0.9600 | C30—O7 | 1.218 (3) |
C8—H8C | 0.9600 | C30—C31 | 1.501 (3) |
C9—O3 | 1.413 (4) | C30—C44 | 1.515 (3) |
C9—H9A | 0.9600 | C31—C32 | 1.375 (3) |
C9—H9B | 0.9600 | C31—C35 | 1.377 (3) |
C9—H9C | 0.9600 | C32—C33 | 1.377 (4) |
C10—C15 | 1.382 (3) | C32—H32 | 0.9300 |
C10—C11 | 1.392 (3) | C33—N3 | 1.325 (4) |
C10—C43 | 1.517 (3) | C33—H33 | 0.9300 |
C11—C12 | 1.387 (3) | N3—C34 | 1.321 (4) |
C11—H11 | 0.9300 | C34—C35 | 1.383 (4) |
C12—O6 | 1.368 (3) | C34—H34 | 0.9300 |
C12—C13 | 1.383 (4) | C35—H35 | 0.9300 |
C13—C14 | 1.382 (4) | C39—C40 | 1.546 (3) |
C13—O5 | 1.383 (3) | C39—C44 | 1.548 (3) |
C14—O4 | 1.371 (3) | C39—H39 | 0.9800 |
C14—C15 | 1.395 (3) | C40—C41 | 1.551 (3) |
C15—H15 | 0.9300 | C40—H40 | 0.9800 |
C16—O4 | 1.402 (4) | C41—O9 | 1.420 (3) |
C16—H16A | 0.9600 | C41—C42 | 1.531 (3) |
C16—H16B | 0.9600 | C42—C43 | 1.534 (3) |
C16—H16C | 0.9600 | C42—H42A | 0.9700 |
C17—O5 | 1.412 (3) | C42—H42B | 0.9700 |
C17—H17A | 0.9600 | C43—C44 | 1.542 (3) |
C17—H17B | 0.9600 | C43—H43 | 0.9800 |
C17—H17C | 0.9600 | C44—H44 | 0.9800 |
C18—O6 | 1.413 (4) | O9—H9 | 0.8200 |
C18—H18A | 0.9600 | O10—H10A | 0.864 (18) |
C18—H18B | 0.9600 | O10—H10B | 0.855 (19) |
C18—H18C | 0.9600 | O11—H11B | 0.851 (18) |
C19—O8 | 1.212 (3) | O11—H11A | 0.873 (17) |
C19—C20 | 1.493 (3) | ||
C6—C1—C2 | 119.6 (2) | C21—C22—H22 | 118.2 |
C6—C1—C39 | 119.2 (2) | C23—N2—C22 | 117.3 (3) |
C2—C1—C39 | 121.2 (2) | N2—C23—C24 | 123.4 (4) |
C3—C2—C1 | 119.7 (2) | N2—C23—H23 | 118.3 |
C3—C2—H2 | 120.1 | C24—C23—H23 | 118.3 |
C1—C2—H2 | 120.1 | C20—C24—C23 | 119.4 (3) |
C4—C3—C2 | 121.2 (2) | C20—C24—H24 | 120.3 |
C4—C3—O1 | 117.6 (2) | C23—C24—H24 | 120.3 |
C2—C3—O1 | 121.2 (2) | C26—C25—C29 | 116.6 (2) |
O2—C4—C3 | 118.5 (3) | C26—C25—C41 | 122.5 (2) |
O2—C4—C5 | 122.5 (3) | C29—C25—C41 | 121.0 (2) |
C3—C4—C5 | 118.8 (2) | C25—C26—C27 | 119.4 (3) |
O3—C5—C6 | 123.4 (3) | C25—C26—H26 | 120.3 |
O3—C5—C4 | 116.3 (2) | C27—C26—H26 | 120.3 |
C6—C5—C4 | 120.3 (2) | N1—C27—C26 | 124.3 (3) |
C1—C6—C5 | 120.3 (2) | N1—C27—H27 | 117.9 |
C1—C6—H6 | 119.9 | C26—C27—H27 | 117.9 |
C5—C6—H6 | 119.9 | C28—N1—C27 | 115.6 (3) |
O1—C7—H7A | 109.5 | N1—C28—C29 | 124.4 (3) |
O1—C7—H7B | 109.5 | N1—C28—H28 | 117.8 |
H7A—C7—H7B | 109.5 | C29—C28—H28 | 117.8 |
O1—C7—H7C | 109.5 | C28—C29—C25 | 119.8 (3) |
H7A—C7—H7C | 109.5 | C28—C29—H29 | 120.1 |
H7B—C7—H7C | 109.5 | C25—C29—H29 | 120.1 |
O1—C7'—H7'1 | 109.5 | O7—C30—C31 | 119.3 (2) |
O1—C7'—H7'2 | 109.5 | O7—C30—C44 | 121.1 (2) |
H7'1—C7'—H7'2 | 109.5 | C31—C30—C44 | 119.4 (2) |
O1—C7'—H7'3 | 109.5 | C32—C31—C35 | 117.9 (2) |
H7'1—C7'—H7'3 | 109.5 | C32—C31—C30 | 119.6 (2) |
H7'2—C7'—H7'3 | 109.5 | C35—C31—C30 | 122.5 (2) |
O2—C8—H8A | 109.5 | C31—C32—C33 | 119.0 (3) |
O2—C8—H8B | 109.5 | C31—C32—H32 | 120.5 |
H8A—C8—H8B | 109.5 | C33—C32—H32 | 120.5 |
O2—C8—H8C | 109.5 | N3—C33—C32 | 123.9 (3) |
H8A—C8—H8C | 109.5 | N3—C33—H33 | 118.0 |
H8B—C8—H8C | 109.5 | C32—C33—H33 | 118.0 |
O3—C9—H9A | 109.5 | C34—N3—C33 | 116.4 (2) |
O3—C9—H9B | 109.5 | N3—C34—C35 | 124.2 (3) |
H9A—C9—H9B | 109.5 | N3—C34—H34 | 117.9 |
O3—C9—H9C | 109.5 | C35—C34—H34 | 117.9 |
H9A—C9—H9C | 109.5 | C31—C35—C34 | 118.5 (3) |
H9B—C9—H9C | 109.5 | C31—C35—H35 | 120.7 |
C15—C10—C11 | 119.7 (2) | C34—C35—H35 | 120.7 |
C15—C10—C43 | 121.2 (2) | C1—C39—C40 | 112.33 (18) |
C11—C10—C43 | 119.1 (2) | C1—C39—C44 | 111.33 (17) |
C12—C11—C10 | 120.1 (2) | C40—C39—C44 | 109.38 (18) |
C12—C11—H11 | 120.0 | C1—C39—H39 | 107.9 |
C10—C11—H11 | 120.0 | C40—C39—H39 | 107.9 |
O6—C12—C13 | 115.2 (2) | C44—C39—H39 | 107.9 |
O6—C12—C11 | 124.4 (3) | C19—C40—C39 | 107.52 (18) |
C13—C12—C11 | 120.4 (3) | C19—C40—C41 | 112.77 (18) |
C14—C13—O5 | 120.7 (3) | C39—C40—C41 | 111.79 (18) |
C14—C13—C12 | 119.5 (2) | C19—C40—H40 | 108.2 |
O5—C13—C12 | 119.8 (3) | C39—C40—H40 | 108.2 |
O4—C14—C13 | 115.7 (2) | C41—C40—H40 | 108.2 |
O4—C14—C15 | 123.8 (3) | O9—C41—C25 | 111.54 (18) |
C13—C14—C15 | 120.5 (3) | O9—C41—C42 | 104.72 (18) |
C10—C15—C14 | 119.8 (3) | C25—C41—C42 | 110.76 (19) |
C10—C15—H15 | 120.1 | O9—C41—C40 | 111.55 (18) |
C14—C15—H15 | 120.1 | C25—C41—C40 | 108.53 (18) |
O4—C16—H16A | 109.5 | C42—C41—C40 | 109.70 (17) |
O4—C16—H16B | 109.5 | C41—C42—C43 | 112.92 (19) |
H16A—C16—H16B | 109.5 | C41—C42—H42A | 109.0 |
O4—C16—H16C | 109.5 | C43—C42—H42A | 109.0 |
H16A—C16—H16C | 109.5 | C41—C42—H42B | 109.0 |
H16B—C16—H16C | 109.5 | C43—C42—H42B | 109.0 |
O5—C17—H17A | 109.5 | H42A—C42—H42B | 107.8 |
O5—C17—H17B | 109.5 | C10—C43—C42 | 113.21 (19) |
H17A—C17—H17B | 109.5 | C10—C43—C44 | 110.89 (18) |
O5—C17—H17C | 109.5 | C42—C43—C44 | 108.46 (18) |
H17A—C17—H17C | 109.5 | C10—C43—H43 | 108.0 |
H17B—C17—H17C | 109.5 | C42—C43—H43 | 108.0 |
O6—C18—H18A | 109.5 | C44—C43—H43 | 108.0 |
O6—C18—H18B | 109.5 | C30—C44—C43 | 113.00 (19) |
H18A—C18—H18B | 109.5 | C30—C44—C39 | 106.86 (18) |
O6—C18—H18C | 109.5 | C43—C44—C39 | 110.83 (17) |
H18A—C18—H18C | 109.5 | C30—C44—H44 | 108.7 |
H18B—C18—H18C | 109.5 | C43—C44—H44 | 108.7 |
O8—C19—C20 | 118.5 (2) | C39—C44—H44 | 108.7 |
O8—C19—C40 | 121.1 (2) | C7—O1—C3 | 119.0 (8) |
C20—C19—C40 | 120.3 (2) | C3—O1—C7' | 115.6 (4) |
C24—C20—C21 | 118.3 (3) | C4—O2—C8 | 117.1 (3) |
C24—C20—C19 | 123.4 (2) | C5—O3—C9 | 117.7 (2) |
C21—C20—C19 | 118.3 (3) | C14—O4—C16 | 118.2 (2) |
C20—C21—C22 | 117.9 (4) | C13—O5—C17 | 113.7 (2) |
C20—C21—H21 | 121.0 | C12—O6—C18 | 118.4 (2) |
C22—C21—H21 | 121.0 | C41—O9—H9 | 109.5 |
N2—C22—C21 | 123.6 (4) | H10A—O10—H10B | 107 (3) |
N2—C22—H22 | 118.2 | H11B—O11—H11A | 107 (2) |
C6—C1—C2—C3 | 1.4 (4) | C30—C31—C35—C34 | −179.0 (3) |
C39—C1—C2—C3 | −178.8 (2) | N3—C34—C35—C31 | 1.3 (5) |
C1—C2—C3—C4 | 0.6 (4) | C6—C1—C39—C40 | −119.8 (2) |
C1—C2—C3—O1 | 179.6 (2) | C2—C1—C39—C40 | 60.3 (3) |
C2—C3—C4—O2 | −177.6 (3) | C6—C1—C39—C44 | 117.1 (2) |
O1—C3—C4—O2 | 3.4 (4) | C2—C1—C39—C44 | −62.8 (3) |
C2—C3—C4—C5 | −3.0 (4) | O8—C19—C40—C39 | 81.9 (3) |
O1—C3—C4—C5 | 177.9 (3) | C20—C19—C40—C39 | −94.0 (3) |
O2—C4—C5—O3 | −2.3 (4) | O8—C19—C40—C41 | −41.8 (3) |
C3—C4—C5—O3 | −176.6 (3) | C20—C19—C40—C41 | 142.3 (2) |
O2—C4—C5—C6 | 177.8 (3) | C1—C39—C40—C19 | 55.1 (2) |
C3—C4—C5—C6 | 3.5 (4) | C44—C39—C40—C19 | 179.28 (18) |
C2—C1—C6—C5 | −0.9 (4) | C1—C39—C40—C41 | 179.42 (18) |
C39—C1—C6—C5 | 179.3 (2) | C44—C39—C40—C41 | −56.4 (2) |
O3—C5—C6—C1 | 178.5 (3) | C26—C25—C41—O9 | −0.6 (3) |
C4—C5—C6—C1 | −1.6 (4) | C29—C25—C41—O9 | −178.7 (2) |
C15—C10—C11—C12 | −0.4 (4) | C26—C25—C41—C42 | −116.8 (2) |
C43—C10—C11—C12 | 176.2 (2) | C29—C25—C41—C42 | 65.1 (3) |
C10—C11—C12—O6 | 179.8 (2) | C26—C25—C41—C40 | 122.7 (2) |
C10—C11—C12—C13 | −1.0 (4) | C29—C25—C41—C40 | −55.4 (3) |
O6—C12—C13—C14 | −178.5 (2) | C19—C40—C41—O9 | 60.3 (2) |
C11—C12—C13—C14 | 2.3 (4) | C39—C40—C41—O9 | −61.0 (2) |
O6—C12—C13—O5 | 3.8 (4) | C19—C40—C41—C25 | −63.0 (2) |
C11—C12—C13—O5 | −175.4 (2) | C39—C40—C41—C25 | 175.68 (18) |
O5—C13—C14—O4 | −3.9 (4) | C19—C40—C41—C42 | 175.8 (2) |
C12—C13—C14—O4 | 178.4 (2) | C39—C40—C41—C42 | 54.5 (2) |
O5—C13—C14—C15 | 175.6 (2) | O9—C41—C42—C43 | 63.8 (2) |
C12—C13—C14—C15 | −2.1 (4) | C25—C41—C42—C43 | −175.82 (19) |
C11—C10—C15—C14 | 0.6 (4) | C40—C41—C42—C43 | −56.0 (3) |
C43—C10—C15—C14 | −175.9 (2) | C15—C10—C43—C42 | −46.1 (3) |
O4—C14—C15—C10 | −179.9 (2) | C11—C10—C43—C42 | 137.3 (2) |
C13—C14—C15—C10 | 0.6 (4) | C15—C10—C43—C44 | 76.0 (3) |
O8—C19—C20—C24 | 139.8 (3) | C11—C10—C43—C44 | −100.6 (2) |
C40—C19—C20—C24 | −44.3 (4) | C41—C42—C43—C10 | −178.05 (19) |
O8—C19—C20—C21 | −40.1 (4) | C41—C42—C43—C44 | 58.4 (2) |
C40—C19—C20—C21 | 135.9 (3) | O7—C30—C44—C43 | 54.1 (3) |
C24—C20—C21—C22 | 0.8 (4) | C31—C30—C44—C43 | −130.5 (2) |
C19—C20—C21—C22 | −179.3 (3) | O7—C30—C44—C39 | −68.1 (3) |
C20—C21—C22—N2 | −2.8 (6) | C31—C30—C44—C39 | 107.3 (2) |
C21—C22—N2—C23 | 2.1 (6) | C10—C43—C44—C30 | 55.8 (3) |
C22—N2—C23—C24 | 0.6 (6) | C42—C43—C44—C30 | −179.26 (18) |
C21—C20—C24—C23 | 1.7 (4) | C10—C43—C44—C39 | 175.7 (2) |
C19—C20—C24—C23 | −178.2 (3) | C42—C43—C44—C39 | −59.4 (2) |
N2—C23—C24—C20 | −2.5 (5) | C1—C39—C44—C30 | −52.7 (2) |
C29—C25—C26—C27 | 0.3 (4) | C40—C39—C44—C30 | −177.41 (18) |
C41—C25—C26—C27 | −177.9 (2) | C1—C39—C44—C43 | −176.18 (19) |
C25—C26—C27—N1 | 0.4 (5) | C40—C39—C44—C43 | 59.1 (2) |
C26—C27—N1—C28 | −0.7 (5) | C4—C3—O1—C7 | −90 (2) |
C27—N1—C28—C29 | 0.3 (5) | C2—C3—O1—C7 | 91 (2) |
N1—C28—C29—C25 | 0.4 (4) | C4—C3—O1—C7' | −138.1 (10) |
C26—C25—C29—C28 | −0.6 (4) | C2—C3—O1—C7' | 42.8 (10) |
C41—C25—C29—C28 | 177.6 (2) | C3—C4—O2—C8 | −122.9 (3) |
O7—C30—C31—C32 | 29.5 (3) | C5—C4—O2—C8 | 62.8 (4) |
C44—C30—C31—C32 | −146.1 (2) | C6—C5—O3—C9 | −18.4 (4) |
O7—C30—C31—C35 | −151.7 (3) | C4—C5—O3—C9 | 161.7 (3) |
C44—C30—C31—C35 | 32.8 (3) | C13—C14—O4—C16 | 176.7 (3) |
C35—C31—C32—C33 | −0.6 (4) | C15—C14—O4—C16 | −2.8 (4) |
C30—C31—C32—C33 | 178.3 (2) | C14—C13—O5—C17 | 84.7 (3) |
C31—C32—C33—N3 | 0.2 (4) | C12—C13—O5—C17 | −97.6 (3) |
C32—C33—N3—C34 | 0.9 (5) | C13—C12—O6—C18 | 169.1 (3) |
C33—N3—C34—C35 | −1.6 (5) | C11—C12—O6—C18 | −11.8 (4) |
C32—C31—C35—C34 | −0.1 (4) |
D—H···A | D—H | H···A | D···A | D—H···A |
C8—H8B···O3 | 0.96 | 2.40 | 2.918 (5) | 114 |
C9—H9B···O7i | 0.96 | 2.63 | 3.575 (4) | 168 |
C11—H11···O8ii | 0.93 | 2.55 | 3.450 (3) | 163 |
C16—H16B···O12 | 0.96 | 2.16 | 2.951 (15) | 139 |
C24—H24···O12iii | 0.93 | 2.57 | 3.192 (15) | 125 |
C27—H27···O4iv | 0.93 | 2.62 | 3.408 (4) | 143 |
C44—H44···O11v | 0.98 | 2.56 | 3.464 (4) | 153 |
O9—H9···O7ii | 0.82 | 2.27 | 2.941 (2) | 139 |
O9—H9···O8 | 0.82 | 2.17 | 2.760 (2) | 129 |
O11—H11B···N2 | 0.85 (2) | 2.02 (2) | 2.861 (4) | 169 (3) |
O11—H11A···O10vi | 0.87 (2) | 1.91 (2) | 2.771 (4) | 171 (3) |
O10—H10A···N3 | 0.86 (2) | 2.00 (2) | 2.857 (4) | 175 (4) |
O10—H10B···O1vi | 0.86 (2) | 2.16 (3) | 2.939 (3) | 151 (5) |
Symmetry codes: (i) −x+3/2, y+1/2, −z+3/2; (ii) −x+1, −y, −z+1; (iii) −x+1/2, y+1/2, −z+3/2; (iv) x−1/2, −y−1/2, z−1/2; (v) −x+1/2, y−1/2, −z+3/2; (vi) −x+1, −y, −z+2. |
Acknowledgements
The authors thank the Central Instrumentation Facility (DST–FIST), Queen Mary's College, Chennai-4, for computing facilities and SAIF, IIT, Madras, for the X-ray data collection facilities.
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