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Resveratrol (RSV) is one of the most extensively investigated natural polyphenol with potential cardioprotective effects and various biological activities. However, the polymorphism and solvates of RSV cocrystals have not been studied comprehensively. In addition, the relationship between the crystal packing modes and their physicochemical properties of RSV cocrystals remains poorly understood. In this paper, seven novel RSV cocrystals were prepared and characterized by powder X-ray diffraction, single-crystal X-ray diffraction, thermogravimetric analysis, differential scanning calorimetry, dynamic vapor sorption, Raman and Fourier transform infrared spectroscopy. Five RSV–4,4′-vinyl­enedi­pyridine (DPE) cocrystals were synthesized with polymorphs and solvates, such as RSV–DPE (1:2) in form (I) [RSV–2DPE form (I)], RSV–DPE (1:2) in form (II) [RSV–2DPE form (II)], RSV–DPE (1:1) (RSV–DPE), RSV–DPE (2:3)·acetone (RSV–1.5DPE·0.5ACE), RSV–DPE (1:1.5)·MeOH (RSV–1.5DPE·MeOH). However, RSV–4,4′-ethyl­enedi­pyridine (BPE) and RSV–4,4′-azobispyridine (AZPY) cocrystals were prepared as their single crystal forms, that is, RSV–BPE (1:1.5) (RSV–1.5BPE) and RSV–AZPY (1:2) (RSV–2AZPY). RSV–2DPE form (II) can be transformed from RSV–2DPE form (I) during the heating process from single crystal to single crystal. The physicochemical properties of RSV cocrystals are closely related to their crystal packing modes. Also, the conformation and molecular packing of RSV among different cocrystals is flexible. The solubility of RSV–1.5BPE and RSV–2DPE form (II) exhibit higher than RSV in the buffer solution of pH 4.6 and 2.0, respectively. This study may provide a valuable insight into the crystal packing modes of cocrystals which may affect their physicochemical properties.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S2052520619013477/aw5030sup1.cif
Contains datablocks RSV-1.5BPE, RSV-2DPE-FormI, RSV-2DPE-FormII, RSV-DPE, RSV-1.5DPE-0.5ACE, RSV-1.5DPE-MeOH, RSV-2AZPY

pdf

Portable Document Format (PDF) file https://doi.org/10.1107/S2052520619013477/aw5030sup9.pdf
Tables S1-S6 and Figs. S1-S22

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S2052520619013477/aw5030RSV-1.5BPEsup2.hkl
Contains datablock RSV-1.5BPE

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S2052520619013477/aw5030RSV-2DPE-FormIsup3.hkl
Contains datablock RSV-2DPE-FormI

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S2052520619013477/aw5030RSV-2DPE-FormIIsup4.hkl
Contains datablock RSV-2DPE-FormII

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S2052520619013477/aw5030RSV-DPEsup5.hkl
Contains datablock RSV-DPE

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S2052520619013477/aw5030RSV-1.5DPE-0.5ACEsup6.hkl
Contains datablock RSV-1.5DPE-0.5ACE

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S2052520619013477/aw5030RSV-1.5DPE-MeOHsup7.hkl
Contains datablock RSV-1.5DPE-MeOH

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S2052520619013477/aw5030RSV-2AZPYsup8.hkl
Contains datablock RSV-2AZPY

CCDC references: 1881579; 1881580; 1881582; 1881583; 1881584; 1881585; 1960764

Computing details top

Cell refinement: SAINT v8.34A (Bruker, 2013) for RSV-1.5BPE, RSV-2DPE-FormI, RSV-2DPE-FormII, RSV-1.5DPE-MeOH, RSV-2AZPY. Data reduction: SAINT v8.34A (Bruker, 2013) for RSV-1.5BPE, RSV-2DPE-FormI, RSV-2DPE-FormII, RSV-1.5DPE-MeOH, RSV-2AZPY. Program(s) used to solve structure: SHELXS1997 (Sheldrick, 2008) for RSV-1.5BPE; ShelXT (Sheldrick, 2015) for RSV-2DPE-FormI, RSV-2DPE-FormII, RSV-DPE, RSV-1.5DPE-0.5ACE; XT (Sheldrick, 2015) for RSV-1.5DPE-MeOH; SIR2004 (Burla et al., 2007) for RSV-2AZPY. For all structures, program(s) used to refine structure: SHELXL (Sheldrick, 2015); molecular graphics: Olex2 (Dolomanov et al., 2009); software used to prepare material for publication: Olex2 (Dolomanov et al., 2009).

(RSV-1.5BPE) top
Crystal data top
2(C14H12O3)·3(C12H12N2)Z = 1
Mr = 1009.18F(000) = 534
Triclinic, P1Dx = 1.245 Mg m3
a = 8.0448 (11) ÅMo Kα radiation, λ = 0.71073 Å
b = 9.9408 (14) ÅCell parameters from 3481 reflections
c = 17.371 (3) Åθ = 2.4–27.4°
α = 104.203 (2)°µ = 0.08 mm1
β = 90.628 (3)°T = 220 K
γ = 91.751 (4)°Block, clear light colourless
V = 1345.9 (3) Å30.19 × 0.15 × 0.11 mm
Data collection top
Bruker APEX-II CCD
diffractometer
4129 reflections with I > 2σ(I)
φ and ω scansRint = 0.027
Absorption correction: multi-scan
SADABS-2014/5 (Bruker,2014/5) was used for absorption correction. wR2(int) was 0.0635 before and 0.0445 after correction. The Ratio of minimum to maximum transmission is 0.9052. The λ/2 correction factor is 0.00150.
θmax = 27.6°, θmin = 1.2°
Tmin = 0.675, Tmax = 0.746h = 1010
12275 measured reflectionsk = 1012
6094 independent reflectionsl = 2222
Refinement top
Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullHydrogen site location: mixed
R[F2 > 2σ(F2)] = 0.066H atoms treated by a mixture of independent and constrained refinement
wR(F2) = 0.222 w = 1/[σ2(Fo2) + (0.1277P)2 + 0.2781P]
where P = (Fo2 + 2Fc2)/3
S = 1.05(Δ/σ)max < 0.001
6094 reflectionsΔρmax = 0.56 e Å3
391 parametersΔρmin = 0.39 e Å3
48 restraints
Special details top

Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/UeqOcc. (<1)
O20.3190 (2)0.36328 (19)0.47493 (8)0.0481 (4)
O30.2216 (2)0.09946 (19)0.20639 (9)0.0516 (5)
O11.3895 (2)0.6223 (2)0.14182 (12)0.0583 (5)
N20.0612 (2)0.0010 (2)0.74080 (11)0.0461 (5)
N30.5060 (2)0.7790 (2)0.04721 (12)0.0493 (5)
C90.5457 (2)0.3543 (2)0.29385 (12)0.0328 (4)
C120.2616 (2)0.2308 (2)0.34152 (11)0.0332 (4)
H120.1658510.1889650.3573780.040*
C100.4991 (2)0.3899 (2)0.37337 (11)0.0346 (4)
H100.5633150.4555140.4110460.041*
C110.3567 (2)0.3276 (2)0.39661 (11)0.0340 (4)
C40.9165 (2)0.4758 (2)0.18421 (12)0.0359 (5)
C80.7010 (2)0.4177 (2)0.27279 (12)0.0355 (5)
H80.7731700.4602400.3153220.043*
C130.3087 (2)0.1960 (2)0.26238 (11)0.0346 (5)
N11.0208 (3)0.2739 (3)0.51822 (13)0.0594 (6)
C70.7513 (3)0.4220 (2)0.20085 (13)0.0382 (5)
H70.6769690.3886420.1578020.046*
C140.4499 (2)0.2575 (2)0.23860 (12)0.0352 (5)
H140.4806000.2336170.1850290.042*
C11.2311 (3)0.5790 (2)0.15328 (14)0.0419 (5)
C61.0979 (3)0.5808 (2)0.10275 (13)0.0453 (6)
H61.1121110.6173190.0581170.054*
C50.9427 (3)0.5284 (2)0.11801 (13)0.0439 (5)
H50.8533320.5284850.0826990.053*
C31.0525 (3)0.4754 (2)0.23381 (14)0.0442 (5)
H3A1.0388750.4393890.2786510.053*
C21.2080 (3)0.5266 (3)0.21927 (15)0.0468 (6)
H2A1.2977010.5256750.2542270.056*
C290.7733 (3)0.9356 (3)0.00840 (14)0.0443 (5)
C270.6063 (3)0.7264 (3)0.01224 (14)0.0484 (6)
H270.5854180.6343660.0414150.058*
C280.7391 (3)0.7995 (3)0.03337 (14)0.0488 (6)
H280.8062850.7574120.0758910.059*
C220.3719 (3)0.0935 (3)0.70067 (14)0.0486 (6)
C240.1695 (3)0.0838 (3)0.70020 (17)0.0532 (6)
H240.1405940.1791330.6856230.064*
C230.3220 (3)0.0421 (3)0.67775 (16)0.0509 (6)
H230.3914430.1073770.6465630.061*
C310.5400 (3)0.9101 (3)0.08766 (15)0.0540 (6)
H310.4710890.9498580.1299560.065*
C300.6707 (3)0.9896 (3)0.07046 (15)0.0521 (6)
H300.6899701.0808800.1011210.062*
C320.9175 (3)1.0205 (3)0.01293 (17)0.0540 (6)
H32A0.9169201.0090740.0705950.065*
H32B0.9022301.1189050.0120110.065*
C180.7284 (3)0.2898 (3)0.53178 (18)0.0628 (7)
H18A0.6353690.3445660.5313690.075*0.5
H180.6306940.3136910.5088760.075*0.5
C210.5410 (4)0.1414 (3)0.67899 (18)0.0688 (9)
H21C0.6278540.0923600.6999890.083*0.5
H21D0.5581580.2410930.7024860.083*0.5
H21A0.5879220.2095570.7253580.083*0.5
H21B0.6132200.0614790.6686350.083*0.5
C250.1112 (4)0.1314 (3)0.7635 (2)0.0818 (11)
H250.0383590.1948350.7936750.098*
C190.8799 (4)0.3262 (3)0.5064 (2)0.0702 (8)
H190.8820040.3953180.4779330.084*
C260.2644 (4)0.1815 (3)0.7460 (2)0.0886 (13)
H260.2943890.2761010.7651710.106*
C17A0.7166 (8)0.1613 (6)0.5597 (4)0.0439 (14)0.5
C20A0.5530 (6)0.1106 (7)0.5847 (3)0.0516 (12)0.5
H20A0.5392640.0103730.5618580.062*0.5
H20B0.4624820.1561660.5639950.062*0.5
C15A1.0026 (8)0.1367 (8)0.5340 (5)0.0749 (17)0.5
H15A1.0946270.0791950.5276580.090*0.5
C16A0.8564 (8)0.0902 (8)0.5576 (4)0.0744 (17)0.5
H16A0.8527710.0058100.5729110.089*0.5
C16B0.8688 (7)0.1920 (8)0.6123 (4)0.0701 (16)0.5
H16B0.8706610.1473330.6540590.084*0.5
C15B1.0156 (6)0.2234 (7)0.5792 (4)0.0604 (14)0.5
H15B1.1164300.2067970.6025120.072*0.5
C20B0.5481 (7)0.1972 (8)0.6173 (4)0.0647 (15)0.5
H20C0.4910780.2853400.6317390.078*0.5
H20D0.4829730.1359730.5738540.078*0.5
C17B0.7183 (7)0.2266 (7)0.5837 (4)0.0475 (14)0.5
H20.218 (4)0.330 (3)0.4846 (18)0.069 (9)*
H11.387 (5)0.668 (4)0.097 (2)0.105 (13)*
H30.128 (4)0.068 (3)0.2294 (16)0.062 (8)*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
O20.0362 (8)0.0664 (11)0.0355 (8)0.0144 (8)0.0076 (6)0.0025 (7)
O30.0444 (9)0.0616 (11)0.0394 (8)0.0282 (8)0.0081 (7)0.0019 (7)
O10.0363 (9)0.0611 (12)0.0816 (12)0.0128 (8)0.0181 (8)0.0263 (10)
N20.0364 (10)0.0441 (11)0.0538 (11)0.0123 (8)0.0094 (8)0.0059 (9)
N30.0376 (10)0.0540 (13)0.0556 (11)0.0109 (9)0.0123 (9)0.0134 (9)
C90.0245 (9)0.0303 (10)0.0436 (10)0.0024 (8)0.0055 (8)0.0093 (8)
C120.0222 (9)0.0381 (11)0.0384 (10)0.0061 (8)0.0047 (7)0.0083 (8)
C100.0270 (9)0.0356 (11)0.0381 (10)0.0067 (8)0.0014 (8)0.0041 (8)
C110.0287 (9)0.0381 (11)0.0342 (9)0.0010 (8)0.0043 (7)0.0067 (8)
C40.0311 (10)0.0311 (11)0.0447 (11)0.0048 (8)0.0095 (8)0.0081 (8)
C80.0267 (9)0.0336 (11)0.0451 (11)0.0071 (8)0.0032 (8)0.0083 (8)
C130.0281 (9)0.0349 (11)0.0383 (10)0.0074 (8)0.0033 (8)0.0050 (8)
N10.0353 (10)0.0901 (18)0.0573 (12)0.0044 (11)0.0141 (9)0.0271 (12)
C70.0295 (10)0.0379 (12)0.0466 (11)0.0070 (8)0.0051 (8)0.0099 (9)
C140.0316 (10)0.0362 (11)0.0361 (9)0.0064 (8)0.0083 (8)0.0061 (8)
C10.0322 (10)0.0333 (11)0.0593 (13)0.0044 (8)0.0162 (9)0.0094 (9)
C60.0489 (13)0.0471 (14)0.0404 (11)0.0092 (10)0.0148 (10)0.0122 (10)
C50.0404 (12)0.0492 (14)0.0412 (11)0.0079 (10)0.0044 (9)0.0103 (10)
C30.0331 (11)0.0478 (14)0.0597 (13)0.0015 (9)0.0073 (10)0.0287 (11)
C20.0298 (10)0.0476 (14)0.0692 (15)0.0037 (9)0.0038 (10)0.0263 (12)
C290.0337 (11)0.0526 (14)0.0500 (12)0.0092 (10)0.0007 (9)0.0203 (10)
C270.0438 (12)0.0454 (14)0.0519 (12)0.0132 (10)0.0081 (10)0.0058 (10)
C280.0381 (12)0.0568 (15)0.0491 (12)0.0093 (10)0.0112 (10)0.0092 (11)
C220.0416 (12)0.0469 (14)0.0529 (13)0.0128 (10)0.0143 (10)0.0050 (10)
C240.0382 (12)0.0357 (13)0.0858 (18)0.0054 (10)0.0059 (12)0.0157 (12)
C230.0344 (11)0.0458 (14)0.0730 (16)0.0034 (10)0.0099 (11)0.0153 (12)
C310.0459 (13)0.0582 (16)0.0551 (13)0.0069 (11)0.0174 (11)0.0091 (12)
C300.0467 (13)0.0454 (14)0.0604 (14)0.0110 (11)0.0045 (11)0.0073 (11)
C320.0386 (12)0.0613 (16)0.0674 (15)0.0148 (11)0.0030 (11)0.0279 (13)
C180.0362 (13)0.080 (2)0.0785 (18)0.0066 (13)0.0122 (12)0.0309 (16)
C210.0502 (15)0.074 (2)0.0731 (17)0.0249 (14)0.0226 (13)0.0035 (15)
C250.0632 (18)0.0464 (16)0.120 (3)0.0097 (13)0.0528 (19)0.0113 (16)
C190.0501 (16)0.073 (2)0.099 (2)0.0003 (14)0.0215 (15)0.0423 (17)
C260.075 (2)0.0414 (16)0.132 (3)0.0201 (14)0.054 (2)0.0120 (17)
C17A0.045 (3)0.040 (3)0.048 (3)0.002 (2)0.015 (2)0.014 (2)
C20A0.042 (2)0.058 (3)0.054 (2)0.013 (2)0.011 (2)0.014 (2)
C15A0.058 (3)0.081 (4)0.096 (4)0.014 (3)0.024 (3)0.038 (3)
C16A0.066 (3)0.075 (3)0.099 (4)0.012 (3)0.023 (3)0.050 (3)
C16B0.052 (3)0.103 (4)0.072 (3)0.002 (3)0.007 (2)0.054 (3)
C15B0.035 (2)0.090 (4)0.066 (3)0.003 (2)0.002 (2)0.038 (3)
C20B0.047 (3)0.080 (4)0.076 (3)0.003 (3)0.008 (2)0.037 (3)
C17B0.032 (2)0.062 (4)0.054 (3)0.004 (3)0.011 (2)0.024 (3)
Geometric parameters (Å, º) top
O2—C111.359 (2)C28—H280.9400
O2—H20.90 (3)C22—C231.355 (3)
O3—C131.358 (2)C22—C211.510 (3)
O3—H30.93 (3)C22—C261.363 (4)
O1—C11.365 (2)C24—H240.9400
O1—H10.98 (4)C24—C231.374 (3)
N2—C241.317 (3)C23—H230.9400
N2—C251.308 (3)C31—H310.9400
N3—C271.330 (3)C31—C301.375 (3)
N3—C311.339 (3)C30—H300.9400
C9—C101.398 (3)C32—C32i1.497 (5)
C9—C81.472 (3)C32—H32A0.9800
C9—C141.388 (3)C32—H32B0.9800
C12—H120.9400C18—H18A0.9400
C12—C111.383 (3)C18—H180.9400
C12—C131.393 (3)C18—C191.369 (4)
C10—H100.9400C18—C17A1.474 (7)
C10—C111.396 (3)C18—C17B1.221 (7)
C4—C71.475 (3)C21—H21C0.9800
C4—C51.390 (3)C21—H21D0.9800
C4—C31.386 (3)C21—H21A0.9800
C8—H80.9400C21—H21B0.9800
C8—C71.328 (3)C21—C20A1.595 (6)
C13—C141.388 (3)C21—C20B1.324 (7)
N1—C191.296 (4)C25—H250.9400
N1—C15A1.459 (8)C25—C261.380 (4)
N1—C15B1.279 (6)C19—H190.9400
C7—H70.9400C26—H260.9400
C14—H140.9400C17A—C20A1.502 (8)
C1—C61.380 (4)C17A—C16A1.343 (9)
C1—C21.383 (3)C20A—H20A0.9800
C6—H60.9400C20A—H20B0.9800
C6—C51.392 (3)C15A—H15A0.9400
C5—H50.9400C15A—C16A1.355 (9)
C3—H3A0.9400C16A—H16A0.9400
C3—C21.384 (3)C16B—H16B0.9400
C2—H2A0.9400C16B—C15B1.379 (7)
C29—C281.387 (3)C16B—C17B1.387 (9)
C29—C301.376 (3)C15B—H15B0.9400
C29—C321.516 (3)C20B—H20C0.9800
C27—H270.9400C20B—H20D0.9800
C27—C281.377 (3)C20B—C17B1.542 (8)
C11—O2—H2112.6 (19)N3—C31—C30123.3 (2)
C13—O3—H3109.4 (17)C30—C31—H31118.3
C1—O1—H1108 (2)C29—C30—H30120.0
C25—N2—C24115.4 (2)C31—C30—C29120.1 (2)
C27—N3—C31116.57 (19)C31—C30—H30120.0
C10—C9—C8117.80 (17)C29—C32—H32A109.0
C14—C9—C10119.73 (17)C29—C32—H32B109.0
C14—C9—C8122.41 (17)C32i—C32—C29112.8 (3)
C11—C12—H12120.3C32i—C32—H32A109.0
C11—C12—C13119.50 (17)C32i—C32—H32B109.0
C13—C12—H12120.3H32A—C32—H32B107.8
C9—C10—H10120.1C19—C18—H18A121.3
C11—C10—C9119.74 (17)C19—C18—H18119.5
C11—C10—H10120.1C19—C18—C17A117.5 (3)
O2—C11—C12122.09 (17)C17A—C18—H18A121.3
O2—C11—C10117.43 (18)C17B—C18—H18119.5
C12—C11—C10120.46 (17)C17B—C18—C19120.9 (4)
C5—C4—C7121.5 (2)C22—C21—H21C109.8
C3—C4—C7121.32 (19)C22—C21—H21D109.8
C3—C4—C5117.14 (18)C22—C21—H21A108.0
C9—C8—H8116.1C22—C21—H21B108.0
C7—C8—C9127.72 (19)C22—C21—C20A109.4 (3)
C7—C8—H8116.1H21C—C21—H21D108.2
O3—C13—C12121.73 (17)H21A—C21—H21B107.2
O3—C13—C14117.74 (17)C20A—C21—H21C109.8
C14—C13—C12120.52 (17)C20A—C21—H21D109.8
C19—N1—C15A113.2 (3)C20B—C21—C22117.2 (4)
C15B—N1—C19111.0 (3)C20B—C21—H21A108.0
C4—C7—H7117.9C20B—C21—H21B108.0
C8—C7—C4124.2 (2)N2—C25—H25118.0
C8—C7—H7117.9N2—C25—C26124.1 (2)
C9—C14—H14120.0C26—C25—H25118.0
C13—C14—C9120.06 (17)N1—C19—C18125.8 (3)
C13—C14—H14120.0N1—C19—H19117.1
O1—C1—C6124.5 (2)C18—C19—H19117.1
O1—C1—C2116.1 (2)C22—C26—C25119.7 (3)
C6—C1—C2119.45 (19)C22—C26—H26120.1
C1—C6—H6120.1C25—C26—H26120.1
C1—C6—C5119.9 (2)C18—C17A—C20A120.7 (5)
C5—C6—H6120.1C16A—C17A—C18116.6 (5)
C4—C5—C6121.6 (2)C16A—C17A—C20A122.6 (6)
C4—C5—H5119.2C21—C20A—H20A109.3
C6—C5—H5119.2C21—C20A—H20B109.3
C4—C3—H3A119.0C17A—C20A—C21111.8 (4)
C2—C3—C4122.0 (2)C17A—C20A—H20A109.3
C2—C3—H3A119.0C17A—C20A—H20B109.3
C1—C2—C3119.9 (2)H20A—C20A—H20B107.9
C1—C2—H2A120.0N1—C15A—H15A119.2
C3—C2—H2A120.0C16A—C15A—N1121.6 (5)
C28—C29—C32121.6 (2)C16A—C15A—H15A119.2
C30—C29—C28116.8 (2)C17A—C16A—C15A121.8 (6)
C30—C29—C32121.6 (2)C17A—C16A—H16A119.1
N3—C27—H27118.2C15A—C16A—H16A119.1
N3—C27—C28123.6 (2)C15B—C16B—H16B120.1
C28—C27—H27118.2C15B—C16B—C17B119.9 (5)
C29—C28—H28120.2C17B—C16B—H16B120.1
C27—C28—C29119.7 (2)N1—C15B—C16B123.0 (5)
C27—C28—H28120.2N1—C15B—H15B118.5
C23—C22—C21120.9 (2)C16B—C15B—H15B118.5
C23—C22—C26116.5 (2)C21—C20B—H20C107.4
C26—C22—C21122.5 (2)C21—C20B—H20D107.4
N2—C24—H24117.9C21—C20B—C17B119.8 (5)
N2—C24—C23124.3 (2)H20C—C20B—H20D106.9
C23—C24—H24117.9C17B—C20B—H20C107.4
C22—C23—C24119.8 (2)C17B—C20B—H20D107.4
C22—C23—H23120.1C18—C17B—C16B115.5 (5)
C24—C23—H23120.1C18—C17B—C20B120.7 (5)
N3—C31—H31118.3C16B—C17B—C20B123.7 (5)
Symmetry code: (i) x+2, y+2, z.
(RSV-2DPE-FormI) top
Crystal data top
C14H12O3·2(C12H10N2)F(000) = 1248
Mr = 592.67Dx = 1.262 Mg m3
Monoclinic, P21/cMo Kα radiation, λ = 0.71073 Å
a = 8.9669 (16) ÅCell parameters from 1985 reflections
b = 36.365 (6) Åθ = 2.2–19.2°
c = 9.6042 (19) ŵ = 0.08 mm1
β = 94.898 (6)°T = 230 K
V = 3120.3 (10) Å3Block, clear yellowish colourless
Z = 40.2 × 0.11 × 0.08 mm
Data collection top
Bruker APEX-II CCD
diffractometer
3368 reflections with I > 2σ(I)
φ and ω scansRint = 0.079
Absorption correction: multi-scan
SADABS-2014/5 (Bruker,2014/5) was used for absorption correction.
θmax = 27.5°, θmin = 2.2°
Tmin = 0.673, Tmax = 0.746h = 1011
28472 measured reflectionsk = 4747
7190 independent reflectionsl = 1212
Refinement top
Refinement on F2Primary atom site location: dual
Least-squares matrix: fullHydrogen site location: mixed
R[F2 > 2σ(F2)] = 0.058H atoms treated by a mixture of independent and constrained refinement
wR(F2) = 0.174 w = 1/[σ2(Fo2) + (0.0695P)2]
where P = (Fo2 + 2Fc2)/3
S = 1.01(Δ/σ)max < 0.001
7190 reflectionsΔρmax = 0.37 e Å3
418 parametersΔρmin = 0.21 e Å3
8 restraints
Special details top

Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
O11.4411 (2)0.27475 (5)1.0440 (2)0.0554 (5)
O20.4016 (2)0.42892 (5)0.73444 (19)0.0555 (5)
O30.7522 (2)0.52049 (5)0.9082 (2)0.0592 (5)
N30.2388 (2)0.48893 (5)0.6494 (2)0.0513 (6)
N40.3079 (2)0.70687 (5)0.4803 (2)0.0510 (6)
N10.5345 (3)0.56683 (5)0.7748 (2)0.0551 (6)
C11.3391 (3)0.30158 (6)1.0144 (2)0.0418 (6)
C21.1869 (3)0.29513 (6)0.9879 (2)0.0435 (6)
H2A1.1503390.2709050.9877010.052*
C31.0892 (3)0.32391 (7)0.9621 (2)0.0460 (6)
H3A0.9862980.3189890.9450580.055*
C41.1390 (3)0.36034 (6)0.9604 (2)0.0475 (6)
C110.5385 (3)0.43941 (6)0.7903 (2)0.0439 (6)
C120.5726 (3)0.47587 (6)0.8224 (2)0.0439 (6)
H120.4992160.4942380.8070830.053*
C130.7156 (3)0.48484 (6)0.8772 (2)0.0450 (6)
C290.0756 (3)0.55191 (6)0.5692 (3)0.0465 (6)
C340.1532 (3)0.64191 (7)0.5555 (3)0.0487 (6)
C170.3781 (3)0.62228 (7)0.6203 (3)0.0486 (7)
C90.7890 (3)0.42123 (7)0.8724 (2)0.0483 (6)
C220.2645 (3)0.69724 (7)0.3449 (3)0.0512 (7)
C140.8241 (3)0.45771 (7)0.9042 (2)0.0464 (6)
H140.9202610.4640160.9435320.056*
C100.6467 (3)0.41249 (7)0.8161 (2)0.0489 (7)
H100.6227570.3878440.7949510.059*
C330.0732 (3)0.60791 (7)0.6012 (3)0.0530 (7)
H330.0708900.6019600.6966120.064*
C71.0373 (3)0.39199 (7)0.9353 (3)0.0528 (7)
H71.0793540.4155500.9481500.063*
C360.2593 (3)0.68409 (7)0.3851 (3)0.0559 (7)
H360.2779040.6904660.2903750.067*
C80.8961 (3)0.39030 (7)0.8972 (3)0.0553 (7)
H80.8560120.3665680.8835280.066*
C200.2975 (3)0.65228 (7)0.5433 (3)0.0532 (7)
H200.2112330.6615490.5801970.064*
C61.3891 (3)0.33760 (7)1.0098 (3)0.0510 (7)
H61.4921790.3425161.0247370.061*
C210.3369 (3)0.66723 (7)0.4262 (3)0.0541 (7)
H210.4226930.6572430.3908220.065*
N20.1407 (3)0.75643 (8)0.1870 (3)0.0861 (8)
C180.3361 (3)0.61091 (7)0.7484 (3)0.0546 (7)
H180.2539710.6219670.7864710.066*
C51.2914 (3)0.36601 (7)0.9839 (3)0.0529 (7)
H51.3288750.3901320.9819660.063*
C320.0056 (3)0.58537 (7)0.5218 (3)0.0525 (6)
H320.0089680.5910060.4260530.063*
C300.0563 (3)0.53388 (7)0.6933 (3)0.0567 (7)
H300.0134590.5426590.7530070.068*
C350.1837 (3)0.65193 (7)0.4168 (3)0.0563 (7)
H350.1528160.6368620.3450680.068*
C310.1398 (3)0.50306 (7)0.7287 (3)0.0562 (7)
H310.1257300.4913980.8138950.067*
C280.1785 (3)0.53715 (7)0.4869 (3)0.0570 (7)
H280.1950570.5481050.4009160.068*
C270.2566 (3)0.50643 (7)0.5310 (3)0.0598 (8)
H270.3275130.4971150.4735520.072*
C160.4959 (3)0.60405 (7)0.5712 (3)0.0590 (8)
H160.5263300.6099430.4826590.071*
C370.2793 (4)0.69645 (7)0.6126 (3)0.0629 (8)
H370.3137580.7115500.6825480.075*
C380.2033 (3)0.66536 (7)0.6533 (3)0.0607 (8)
H380.1849810.6599040.7489340.073*
C150.5696 (3)0.57750 (7)0.6491 (3)0.0616 (8)
H150.6508250.5658660.6116510.074*
C260.1311 (3)0.71328 (8)0.3724 (3)0.0612 (8)
H260.0785220.7044740.4461360.073*
C190.4150 (3)0.58325 (8)0.8204 (3)0.0580 (7)
H190.3827170.5755910.9063860.070*
C230.3326 (3)0.71179 (8)0.2329 (3)0.0669 (8)
H230.4228020.7016560.2072960.080*
C250.0753 (4)0.74196 (9)0.2925 (3)0.0742 (9)
H250.0162910.7521670.3140090.089*
C240.2694 (4)0.74059 (10)0.1601 (4)0.0883 (11)
H240.3195740.7500230.0857920.106*
H20.344 (3)0.4479 (6)0.706 (3)0.079 (10)*
H11.401 (3)0.2534 (5)1.040 (3)0.065 (9)*
H30.685 (3)0.5359 (7)0.882 (3)0.073 (10)*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
O10.0430 (11)0.0442 (11)0.0782 (14)0.0036 (9)0.0007 (10)0.0023 (10)
O20.0560 (13)0.0448 (11)0.0638 (12)0.0004 (10)0.0051 (10)0.0037 (9)
O30.0554 (13)0.0529 (13)0.0679 (13)0.0035 (10)0.0033 (11)0.0025 (10)
N30.0459 (14)0.0488 (13)0.0575 (14)0.0033 (10)0.0058 (12)0.0043 (10)
N40.0524 (14)0.0476 (13)0.0518 (14)0.0036 (10)0.0020 (12)0.0016 (10)
N10.0591 (15)0.0477 (13)0.0580 (15)0.0114 (11)0.0017 (13)0.0005 (10)
C10.0455 (16)0.0431 (14)0.0371 (14)0.0021 (12)0.0052 (12)0.0007 (10)
C20.0460 (16)0.0402 (14)0.0449 (14)0.0024 (12)0.0069 (13)0.0001 (11)
C30.0410 (16)0.0567 (16)0.0397 (14)0.0001 (13)0.0004 (12)0.0001 (11)
C40.0635 (19)0.0468 (14)0.0327 (13)0.0028 (11)0.0066 (13)0.0055 (10)
C110.0505 (17)0.0434 (15)0.0380 (14)0.0024 (13)0.0052 (13)0.0048 (11)
C120.0448 (16)0.0456 (15)0.0412 (14)0.0039 (12)0.0025 (13)0.0055 (11)
C130.0544 (18)0.0446 (15)0.0369 (14)0.0043 (13)0.0088 (13)0.0023 (11)
C290.0413 (15)0.0502 (13)0.0464 (15)0.0105 (10)0.0045 (13)0.0021 (11)
C340.0493 (17)0.0508 (14)0.0457 (15)0.0057 (10)0.0022 (13)0.0026 (11)
C170.0479 (17)0.0505 (15)0.0468 (15)0.0142 (13)0.0009 (14)0.0062 (12)
C90.0556 (17)0.0562 (11)0.0342 (13)0.0047 (10)0.0104 (13)0.0036 (11)
C220.0501 (18)0.0573 (16)0.0453 (15)0.0080 (13)0.0004 (14)0.0046 (12)
C140.0414 (15)0.0608 (12)0.0368 (14)0.0021 (12)0.0027 (12)0.0028 (11)
C100.0603 (19)0.0452 (15)0.0410 (15)0.0076 (13)0.0031 (13)0.0003 (11)
C330.0549 (18)0.0573 (14)0.0461 (15)0.0004 (12)0.0009 (14)0.0041 (12)
C70.061 (2)0.0555 (15)0.0418 (15)0.0068 (11)0.0018 (14)0.0044 (12)
C360.0582 (19)0.0704 (19)0.0392 (15)0.0011 (15)0.0049 (14)0.0055 (13)
C80.0580 (19)0.0601 (16)0.0473 (16)0.0074 (11)0.0027 (15)0.0019 (12)
C200.0503 (18)0.0622 (17)0.0477 (16)0.0106 (14)0.0083 (14)0.0030 (13)
C60.0451 (17)0.0485 (16)0.0596 (17)0.0054 (13)0.0048 (14)0.0017 (12)
C210.0562 (18)0.0548 (16)0.0518 (16)0.0111 (13)0.0081 (15)0.0062 (13)
N20.077 (2)0.111 (2)0.0720 (19)0.0308 (17)0.0159 (16)0.0251 (16)
C180.0525 (18)0.0696 (18)0.0425 (15)0.0055 (14)0.0080 (14)0.0037 (13)
C50.061 (2)0.0449 (15)0.0527 (16)0.0042 (14)0.0067 (15)0.0018 (12)
C320.0543 (17)0.0540 (14)0.0489 (15)0.0016 (11)0.0021 (14)0.0027 (12)
C300.0490 (17)0.0601 (17)0.0629 (19)0.0012 (14)0.0163 (15)0.0053 (14)
C350.0606 (19)0.0652 (18)0.0440 (16)0.0116 (15)0.0096 (14)0.0016 (13)
C310.0521 (18)0.0627 (18)0.0539 (17)0.0053 (15)0.0049 (15)0.0142 (14)
C280.072 (2)0.0551 (17)0.0445 (15)0.0008 (15)0.0092 (15)0.0024 (12)
C270.067 (2)0.0581 (18)0.0555 (17)0.0050 (15)0.0136 (16)0.0010 (14)
C160.070 (2)0.0585 (18)0.0514 (16)0.0058 (15)0.0195 (16)0.0032 (13)
C370.095 (2)0.0476 (16)0.0455 (17)0.0050 (15)0.0041 (17)0.0068 (12)
C380.091 (2)0.0543 (17)0.0359 (15)0.0083 (15)0.0013 (15)0.0017 (12)
C150.069 (2)0.0522 (17)0.0665 (19)0.0054 (15)0.0208 (17)0.0012 (14)
C260.0548 (19)0.083 (2)0.0467 (16)0.0002 (16)0.0077 (15)0.0018 (15)
C190.0600 (19)0.0696 (19)0.0449 (16)0.0131 (16)0.0080 (15)0.0047 (14)
C230.0511 (19)0.091 (2)0.0595 (18)0.0077 (16)0.0134 (15)0.0167 (16)
C250.064 (2)0.107 (3)0.0515 (18)0.0225 (19)0.0071 (17)0.0006 (17)
C240.068 (2)0.119 (3)0.080 (2)0.022 (2)0.0218 (19)0.047 (2)
Geometric parameters (Å, º) top
O1—C11.351 (3)C14—H140.9400
O1—H10.855 (16)C10—H100.9400
O2—C111.352 (3)C33—H330.9400
O2—H20.893 (17)C33—C321.304 (3)
O3—C131.364 (3)C7—H70.9400
O3—H30.845 (17)C7—C81.289 (4)
N3—C311.322 (3)C36—H360.9400
N3—C271.325 (3)C36—C351.373 (3)
N4—C361.334 (3)C8—H80.9400
N4—C371.330 (3)C20—H200.9400
N1—C151.332 (3)C20—C211.324 (3)
N1—C191.333 (3)C6—H60.9400
C1—C21.386 (3)C6—C51.364 (3)
C1—C61.386 (3)C21—H210.9400
C2—H2A0.9400N2—C251.322 (4)
C2—C31.374 (3)N2—C241.335 (4)
C3—H3A0.9400C18—H180.9400
C3—C41.399 (3)C18—C191.381 (4)
C4—C71.475 (4)C5—H50.9400
C4—C51.382 (4)C32—H320.9400
C11—C121.389 (3)C30—H300.9400
C11—C101.386 (3)C30—C311.374 (4)
C12—H120.9400C35—H350.9400
C12—C131.383 (3)C31—H310.9400
C13—C141.394 (3)C28—H280.9400
C29—C321.470 (3)C28—C271.366 (4)
C29—C301.384 (3)C27—H270.9400
C29—C281.374 (4)C16—H160.9400
C34—C331.477 (3)C16—C151.358 (4)
C34—C351.385 (3)C37—H370.9400
C34—C381.373 (3)C37—C381.360 (4)
C17—C201.473 (4)C38—H380.9400
C17—C181.380 (3)C15—H150.9400
C17—C161.364 (4)C26—H260.9400
C9—C141.391 (3)C26—C251.364 (4)
C9—C101.379 (4)C19—H190.9400
C9—C81.485 (4)C23—H230.9400
C22—C211.462 (4)C23—C241.356 (4)
C22—C261.376 (4)C25—H250.9400
C22—C231.387 (4)C24—H240.9400
C1—O1—H1111.9 (19)C21—C20—C17125.1 (3)
C11—O2—H2112.9 (18)C21—C20—H20117.4
C13—O3—H3114 (2)C1—C6—H6119.4
C31—N3—C27116.3 (2)C5—C6—C1121.1 (3)
C37—N4—C36115.4 (2)C5—C6—H6119.4
C15—N1—C19115.3 (2)C22—C21—H21115.8
O1—C1—C2123.7 (2)C20—C21—C22128.4 (3)
O1—C1—C6118.3 (2)C20—C21—H21115.8
C6—C1—C2118.1 (2)C25—N2—C24115.1 (3)
C1—C2—H2A119.8C17—C18—H18120.1
C3—C2—C1120.5 (2)C17—C18—C19119.8 (3)
C3—C2—H2A119.8C19—C18—H18120.1
C2—C3—H3A119.2C4—C5—H5119.1
C2—C3—C4121.6 (2)C6—C5—C4121.9 (2)
C4—C3—H3A119.2C6—C5—H5119.1
C3—C4—C7123.2 (3)C29—C32—H32117.2
C5—C4—C3116.9 (2)C33—C32—C29125.6 (3)
C5—C4—C7120.0 (2)C33—C32—H32117.2
O2—C11—C12122.1 (2)C29—C30—H30120.2
O2—C11—C10118.0 (2)C31—C30—C29119.6 (3)
C10—C11—C12119.8 (2)C31—C30—H30120.2
C11—C12—H12120.4C34—C35—H35120.3
C13—C12—C11119.2 (2)C36—C35—C34119.3 (2)
C13—C12—H12120.4C36—C35—H35120.3
O3—C13—C12120.4 (2)N3—C31—C30123.6 (2)
O3—C13—C14118.8 (2)N3—C31—H31118.2
C12—C13—C14120.9 (2)C30—C31—H31118.2
C30—C29—C32124.3 (3)C29—C28—H28120.2
C28—C29—C32119.0 (2)C27—C28—C29119.5 (2)
C28—C29—C30116.7 (2)C27—C28—H28120.2
C35—C34—C33123.8 (2)N3—C27—C28124.3 (3)
C38—C34—C33119.7 (2)N3—C27—H27117.9
C38—C34—C35116.5 (2)C28—C27—H27117.9
C18—C17—C20120.6 (3)C17—C16—H16119.7
C16—C17—C20123.2 (2)C15—C16—C17120.7 (3)
C16—C17—C18116.1 (3)C15—C16—H16119.7
C14—C9—C8123.8 (3)N4—C37—H37117.9
C10—C9—C14119.3 (2)N4—C37—C38124.2 (2)
C10—C9—C8116.9 (2)C38—C37—H37117.9
C26—C22—C21124.6 (3)C34—C38—H38119.8
C26—C22—C23115.8 (3)C37—C38—C34120.3 (2)
C23—C22—C21119.6 (3)C37—C38—H38119.8
C13—C14—H14120.2N1—C15—C16124.4 (3)
C9—C14—C13119.5 (2)N1—C15—H15117.8
C9—C14—H14120.2C16—C15—H15117.8
C11—C10—H10119.4C22—C26—H26120.0
C9—C10—C11121.2 (2)C25—C26—C22119.9 (3)
C9—C10—H10119.4C25—C26—H26120.0
C34—C33—H33116.9N1—C19—C18123.6 (2)
C32—C33—C34126.2 (3)N1—C19—H19118.2
C32—C33—H33116.9C18—C19—H19118.2
C4—C7—H7117.0C22—C23—H23119.9
C8—C7—C4126.0 (3)C24—C23—C22120.1 (3)
C8—C7—H7117.0C24—C23—H23119.9
N4—C36—H36117.9N2—C25—C26124.7 (3)
N4—C36—C35124.2 (2)N2—C25—H25117.6
C35—C36—H36117.9C26—C25—H25117.6
C9—C8—H8116.0N2—C24—C23124.3 (3)
C7—C8—C9128.0 (3)N2—C24—H24117.9
C7—C8—H8116.0C23—C24—H24117.9
C17—C20—H20117.4
(RSV-2DPE-FormII) top
Crystal data top
C14H12O3·2(C12H10N2)Z = 2
Mr = 592.67F(000) = 624
Triclinic, P1Dx = 1.261 Mg m3
a = 9.718 (3) ÅMo Kα radiation, λ = 0.71073 Å
b = 12.072 (4) ÅCell parameters from 2497 reflections
c = 15.426 (5) Åθ = 2.5–25.1°
α = 72.697 (4)°µ = 0.08 mm1
β = 72.681 (5)°T = 220 K
γ = 67.465 (6)°Block, clear whiteish colourless
V = 1560.9 (8) Å30.2 × 0.15 × 0.08 mm
Data collection top
Bruker APEX-II CCD
diffractometer
3196 reflections with I > 2σ(I)
ω scansRint = 0.037
Absorption correction: multi-scan
SADABS-2014/5 (Bruker,2014/5) was used for absorption correction. wR2(int) was 0.0681 before and 0.0473 after correction. The Ratio of minimum to maximum transmission is 0.8095. The λ/2 correction factor is 0.00150.
θmax = 25.0°, θmin = 1.4°
Tmin = 0.604, Tmax = 0.746h = 1011
10193 measured reflectionsk = 1214
5357 independent reflectionsl = 1818
Refinement top
Refinement on F2Primary atom site location: dual
Least-squares matrix: fullHydrogen site location: mixed
R[F2 > 2σ(F2)] = 0.076H atoms treated by a mixture of independent and constrained refinement
wR(F2) = 0.283 w = 1/[σ2(Fo2) + (0.2P)2]
where P = (Fo2 + 2Fc2)/3
S = 0.99(Δ/σ)max = 0.001
5357 reflectionsΔρmax = 0.41 e Å3
436 parametersΔρmin = 0.39 e Å3
90 restraints
Special details top

Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/UeqOcc. (<1)
O30.1818 (3)0.4689 (2)0.23593 (19)0.0597 (7)
O11.4001 (3)0.0064 (3)0.19658 (19)0.0607 (8)
O20.2864 (3)0.6208 (3)0.45601 (19)0.0669 (8)
N30.5590 (3)0.8017 (3)0.11591 (19)0.0472 (7)
N10.1042 (3)0.3554 (3)0.7201 (2)0.0586 (9)
N20.9988 (3)0.2183 (3)0.4647 (2)0.0588 (9)
C61.1532 (4)0.0068 (3)0.1833 (2)0.0440 (8)
H61.1946340.0643230.1585700.053*
C11.2475 (3)0.0493 (3)0.2072 (2)0.0414 (8)
C290.8091 (3)0.6057 (3)0.0588 (2)0.0386 (8)
N40.7945 (4)0.0809 (3)0.0398 (2)0.0610 (9)
C40.9318 (3)0.1746 (3)0.2327 (2)0.0419 (8)
C90.5264 (3)0.3881 (3)0.3210 (2)0.0402 (8)
C320.9399 (4)0.4989 (3)0.0334 (2)0.0417 (8)
H320.9366080.4212890.0686640.050*
C280.8001 (3)0.7267 (3)0.0158 (2)0.0433 (8)
H280.8782760.7443580.0333550.052*
C130.2770 (3)0.4704 (3)0.2853 (2)0.0437 (8)
C350.6432 (4)0.3372 (3)0.0008 (2)0.0476 (8)
C80.6887 (4)0.3111 (3)0.3074 (2)0.0450 (8)
H80.7440900.3151520.3463610.054*
C140.4255 (3)0.3900 (3)0.2711 (2)0.0442 (8)
H140.4576980.3380990.2289710.053*
C70.7669 (3)0.2376 (3)0.2486 (2)0.0446 (8)
H70.7120890.2243940.2137570.054*
C50.9977 (4)0.0686 (3)0.1958 (2)0.0452 (8)
H50.9352200.0386720.1790740.054*
C100.4775 (3)0.4653 (3)0.3827 (2)0.0467 (9)
H100.5447830.4638260.4162710.056*
C110.3276 (4)0.5453 (3)0.3950 (2)0.0474 (9)
C340.5654 (4)0.2540 (3)0.0528 (3)0.0519 (9)
H340.4599710.2823830.0764840.062*
C120.2288 (3)0.5477 (3)0.3462 (2)0.0446 (8)
H120.1283920.6020610.3543490.054*
C31.0306 (4)0.2175 (3)0.2538 (2)0.0459 (8)
H3A0.9902830.2897090.2771540.055*
C170.3686 (4)0.1830 (4)0.6443 (3)0.0606 (11)
C360.7998 (4)0.2841 (3)0.0303 (3)0.0540 (9)
H360.8589100.3346480.0654370.065*
C21.1862 (4)0.1564 (3)0.2411 (2)0.0536 (10)
H2A1.2499760.1874920.2554480.064*
C310.5672 (4)0.6856 (4)0.1552 (2)0.0565 (10)
H310.4854020.6704570.2023840.068*
C300.6884 (4)0.5871 (3)0.1304 (2)0.0513 (9)
H300.6899150.5070710.1617980.062*
C270.6748 (4)0.8204 (3)0.0464 (2)0.0485 (9)
H270.6703440.9015660.0170280.058*
C370.8678 (4)0.1605 (4)0.0106 (3)0.0614 (10)
H370.9729880.1290760.0338530.074*
C380.5715 (4)0.4714 (3)0.0184 (2)0.0501 (9)
H380.6306360.5193940.0591540.060*
C230.7439 (5)0.1646 (5)0.5533 (3)0.0773 (14)
H230.6636080.1910040.5938320.093*
C240.8812 (5)0.2503 (4)0.5227 (3)0.0653 (11)
H240.8916560.3340590.5437690.078*
C330.6442 (4)0.1313 (4)0.0687 (3)0.0614 (10)
H330.5883080.0778870.1026540.074*
C220.7246 (5)0.0401 (5)0.5243 (3)0.0759 (15)
C250.9768 (5)0.0993 (4)0.4342 (3)0.0654 (11)
H251.0565440.0746550.3910390.079*
C260.8440 (6)0.0092 (4)0.4621 (3)0.0753 (13)
H260.8358070.0738290.4380750.090*
C150.2140 (5)0.3888 (4)0.6543 (3)0.0738 (12)
H150.2009650.4728790.6325510.089*
C190.1293 (5)0.2359 (4)0.7463 (3)0.0816 (15)
H190.0536180.2084850.7917000.098*
C160.3454 (5)0.3065 (5)0.6166 (3)0.0816 (14)
H160.4201870.3351850.5713110.098*
C180.2574 (5)0.1497 (4)0.7119 (4)0.0866 (15)
H180.2686300.0661080.7354220.104*
C200.4929 (8)0.0695 (9)0.6184 (5)0.0506 (17)0.6
H200.4888370.0077400.6539560.061*0.6
C210.6056 (7)0.0756 (9)0.5482 (4)0.0554 (18)0.6
H210.6124050.1521570.5126510.066*0.6
C1AA0.5667 (11)0.0065 (10)0.5817 (7)0.043 (2)0.4
H1AA0.5044670.0427530.6131190.052*0.4
C0AA0.5249 (12)0.1251 (10)0.5832 (10)0.044 (2)0.4
H0AA0.5883820.1722500.5481870.052*0.4
H11.416 (4)0.063 (3)0.169 (3)0.066 (13)*
H30.092 (3)0.522 (3)0.253 (3)0.082 (14)*
H20.192 (3)0.668 (3)0.463 (3)0.078 (13)*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
O30.0356 (13)0.0656 (18)0.0845 (18)0.0041 (12)0.0104 (13)0.0436 (14)
O10.0293 (12)0.0715 (19)0.0819 (18)0.0019 (12)0.0035 (12)0.0441 (15)
O20.0394 (14)0.081 (2)0.0796 (18)0.0109 (13)0.0195 (13)0.0497 (15)
N30.0376 (15)0.0456 (18)0.0518 (16)0.0035 (12)0.0034 (12)0.0198 (13)
N10.0355 (15)0.074 (2)0.071 (2)0.0076 (15)0.0069 (14)0.0392 (17)
N20.0411 (17)0.064 (2)0.0601 (18)0.0031 (15)0.0059 (14)0.0281 (16)
C60.0389 (17)0.0345 (17)0.0546 (19)0.0073 (14)0.0033 (15)0.0225 (14)
C10.0274 (15)0.0451 (19)0.0458 (17)0.0043 (13)0.0000 (13)0.0185 (14)
C290.0365 (17)0.0363 (18)0.0437 (16)0.0086 (13)0.0051 (13)0.0165 (13)
N40.0562 (19)0.0493 (19)0.080 (2)0.0093 (15)0.0139 (17)0.0283 (16)
C40.0328 (16)0.0374 (18)0.0500 (18)0.0082 (13)0.0032 (14)0.0107 (14)
C90.0298 (16)0.0355 (17)0.0443 (16)0.0035 (13)0.0035 (13)0.0063 (13)
C320.0432 (17)0.0279 (16)0.0485 (18)0.0053 (14)0.0079 (13)0.0100 (13)
C280.0366 (17)0.0379 (19)0.0521 (18)0.0099 (14)0.0024 (14)0.0191 (15)
C130.0300 (16)0.0470 (19)0.0528 (19)0.0108 (14)0.0020 (14)0.0174 (15)
C350.0479 (19)0.047 (2)0.0551 (19)0.0130 (16)0.0130 (16)0.0220 (16)
C80.0302 (16)0.049 (2)0.0463 (17)0.0052 (14)0.0048 (13)0.0103 (15)
C140.0337 (16)0.0407 (19)0.0497 (18)0.0027 (14)0.0038 (14)0.0149 (15)
C70.0304 (16)0.0428 (19)0.0561 (19)0.0069 (14)0.0069 (14)0.0127 (15)
C50.0365 (17)0.0445 (19)0.0544 (19)0.0124 (14)0.0046 (14)0.0157 (15)
C100.0298 (16)0.058 (2)0.0484 (18)0.0070 (15)0.0059 (14)0.0166 (16)
C110.0354 (17)0.050 (2)0.0505 (19)0.0016 (15)0.0054 (15)0.0218 (16)
C340.0459 (19)0.047 (2)0.073 (2)0.0155 (16)0.0108 (17)0.0272 (18)
C120.0268 (15)0.048 (2)0.0543 (19)0.0005 (13)0.0085 (14)0.0197 (15)
C30.0405 (18)0.0414 (19)0.0559 (19)0.0059 (14)0.0014 (15)0.0286 (15)
C170.0371 (19)0.079 (3)0.065 (2)0.0050 (18)0.0181 (18)0.037 (2)
C360.0442 (19)0.051 (2)0.064 (2)0.0129 (16)0.0052 (17)0.0178 (17)
C20.0355 (17)0.067 (2)0.066 (2)0.0129 (16)0.0015 (16)0.0387 (19)
C310.0396 (18)0.061 (2)0.055 (2)0.0106 (17)0.0057 (16)0.0161 (18)
C300.049 (2)0.0358 (19)0.055 (2)0.0107 (15)0.0004 (16)0.0039 (15)
C270.0395 (17)0.0376 (19)0.065 (2)0.0069 (14)0.0036 (16)0.0211 (16)
C370.049 (2)0.054 (2)0.078 (3)0.0073 (18)0.0065 (19)0.027 (2)
C380.0453 (18)0.050 (2)0.060 (2)0.0130 (15)0.0099 (16)0.0226 (16)
C230.044 (2)0.124 (4)0.054 (2)0.024 (2)0.0004 (18)0.019 (2)
C240.059 (2)0.063 (3)0.070 (2)0.014 (2)0.016 (2)0.012 (2)
C330.057 (2)0.056 (2)0.081 (3)0.0243 (19)0.014 (2)0.021 (2)
C220.059 (3)0.095 (4)0.054 (2)0.022 (2)0.022 (2)0.038 (2)
C250.062 (2)0.066 (3)0.054 (2)0.014 (2)0.0011 (19)0.0143 (19)
C260.095 (3)0.049 (2)0.069 (3)0.005 (2)0.034 (3)0.013 (2)
C150.056 (2)0.056 (3)0.105 (3)0.016 (2)0.006 (2)0.023 (2)
C190.047 (2)0.074 (3)0.096 (3)0.018 (2)0.014 (2)0.010 (3)
C160.050 (2)0.090 (4)0.086 (3)0.021 (2)0.019 (2)0.025 (3)
C180.059 (3)0.054 (3)0.117 (4)0.005 (2)0.007 (3)0.004 (2)
C200.043 (4)0.043 (5)0.058 (4)0.006 (4)0.012 (3)0.009 (4)
C210.044 (4)0.051 (4)0.048 (4)0.003 (4)0.002 (3)0.009 (3)
C1AA0.030 (4)0.042 (5)0.047 (5)0.005 (5)0.006 (4)0.007 (5)
C0AA0.031 (5)0.036 (6)0.069 (7)0.013 (5)0.005 (5)0.021 (6)
Geometric parameters (Å, º) top
O3—C131.371 (4)C11—C121.373 (5)
O3—H30.881 (19)C34—H340.9400
O1—C11.354 (4)C34—C331.366 (5)
O1—H10.853 (19)C12—H120.9400
O2—C111.371 (4)C3—H3A0.9400
O2—H20.870 (19)C3—C21.387 (4)
N3—C311.332 (5)C17—C161.370 (7)
N3—C271.341 (4)C17—C181.352 (6)
N1—C151.332 (5)C17—C201.505 (9)
N1—C191.322 (5)C17—C0AA1.553 (13)
N2—C241.334 (5)C36—H360.9400
N2—C251.325 (5)C36—C371.360 (5)
C6—H60.9400C2—H2A0.9400
C6—C11.383 (5)C31—H310.9400
C6—C51.388 (4)C31—C301.369 (5)
C1—C21.388 (5)C30—H300.9400
C29—C321.477 (4)C27—H270.9400
C29—C281.393 (5)C37—H370.9400
C29—C301.389 (4)C38—C38ii1.326 (6)
N4—C371.336 (5)C38—H380.9400
N4—C331.340 (5)C23—H230.9400
C4—C71.466 (4)C23—C241.390 (6)
C4—C51.400 (5)C23—C221.389 (7)
C4—C31.401 (5)C24—H240.9400
C9—C81.480 (4)C33—H330.9400
C9—C141.406 (5)C22—C261.365 (7)
C9—C101.385 (5)C22—C211.496 (9)
C32—C32i1.310 (6)C22—C1AA1.511 (11)
C32—H320.9400C25—H250.9400
C28—H280.9400C25—C261.380 (6)
C28—C271.379 (4)C26—H260.9400
C13—C141.392 (4)C15—H150.9400
C13—C121.377 (5)C15—C161.372 (6)
C35—C341.402 (5)C19—H190.9400
C35—C361.399 (5)C19—C181.362 (6)
C35—C381.474 (5)C16—H160.9400
C8—H80.9400C18—H180.9400
C8—C71.319 (5)C20—H200.9400
C14—H140.9400C20—C211.298 (9)
C7—H70.9400C21—H210.9400
C5—H50.9400C1AA—H1AA0.9400
C10—H100.9400C1AA—C0AA1.336 (15)
C10—C111.399 (4)C0AA—H0AA0.9400
C13—O3—H3107 (3)C35—C36—H36119.5
C1—O1—H1103 (3)C37—C36—C35121.1 (4)
C11—O2—H2115 (3)C37—C36—H36119.5
C31—N3—C27116.9 (3)C1—C2—H2A120.1
C19—N1—C15115.0 (3)C3—C2—C1119.9 (3)
C25—N2—C24116.6 (3)C3—C2—H2A120.1
C1—C6—H6119.9N3—C31—H31118.2
C1—C6—C5120.3 (3)N3—C31—C30123.6 (3)
C5—C6—H6119.9C30—C31—H31118.2
O1—C1—C6123.3 (3)C29—C30—H30120.1
O1—C1—C2117.2 (3)C31—C30—C29119.9 (3)
C6—C1—C2119.5 (3)C31—C30—H30120.1
C28—C29—C32123.6 (3)N3—C27—C28123.5 (3)
C30—C29—C32119.4 (3)N3—C27—H27118.2
C30—C29—C28117.0 (3)C28—C27—H27118.2
C37—N4—C33114.9 (3)N4—C37—C36124.1 (3)
C5—C4—C7121.4 (3)N4—C37—H37117.9
C5—C4—C3116.9 (3)C36—C37—H37117.9
C3—C4—C7121.6 (3)C35—C38—H38118.1
C14—C9—C8122.9 (3)C38ii—C38—C35123.8 (5)
C10—C9—C8116.9 (3)C38ii—C38—H38118.1
C10—C9—C14120.1 (3)C24—C23—H23119.8
C29—C32—H32116.7C22—C23—H23119.8
C32i—C32—C29126.6 (4)C22—C23—C24120.4 (4)
C32i—C32—H32116.7N2—C24—C23122.5 (4)
C29—C28—H28120.4N2—C24—H24118.7
C27—C28—C29119.1 (3)C23—C24—H24118.7
C27—C28—H28120.4N4—C33—C34125.4 (4)
O3—C13—C14116.9 (3)N4—C33—H33117.3
O3—C13—C12121.8 (3)C34—C33—H33117.3
C12—C13—C14121.3 (3)C23—C22—C21136.1 (5)
C34—C35—C38124.3 (3)C23—C22—C1AA97.9 (6)
C36—C35—C34115.0 (3)C26—C22—C23116.1 (4)
C36—C35—C38120.6 (3)C26—C22—C21107.7 (5)
C9—C8—H8115.3C26—C22—C1AA146.0 (6)
C7—C8—C9129.4 (3)N2—C25—H25118.0
C7—C8—H8115.3N2—C25—C26124.0 (4)
C9—C14—H14120.7C26—C25—H25118.0
C13—C14—C9118.6 (3)C22—C26—C25120.3 (4)
C13—C14—H14120.7C22—C26—H26119.8
C4—C7—H7117.1C25—C26—H26119.8
C8—C7—C4125.7 (3)N1—C15—H15118.3
C8—C7—H7117.1N1—C15—C16123.3 (4)
C6—C5—C4121.5 (3)C16—C15—H15118.3
C6—C5—H5119.2N1—C19—H19117.8
C4—C5—H5119.2N1—C19—C18124.5 (4)
C9—C10—H10120.1C18—C19—H19117.8
C9—C10—C11119.9 (3)C17—C16—C15120.7 (4)
C11—C10—H10120.1C17—C16—H16119.6
O2—C11—C10117.2 (3)C15—C16—H16119.6
O2—C11—C12122.5 (3)C17—C18—C19120.8 (4)
C12—C11—C10120.3 (3)C17—C18—H18119.6
C35—C34—H34120.3C19—C18—H18119.6
C33—C34—C35119.4 (3)C17—C20—H20119.1
C33—C34—H34120.3C21—C20—C17121.7 (10)
C13—C12—H12120.0C21—C20—H20119.1
C11—C12—C13119.9 (3)C22—C21—H21120.2
C11—C12—H12120.0C20—C21—C22119.6 (9)
C4—C3—H3A119.1C20—C21—H21120.2
C2—C3—C4121.8 (3)C22—C1AA—H1AA123.6
C2—C3—H3A119.1C0AA—C1AA—C22112.8 (12)
C16—C17—C20135.3 (5)C0AA—C1AA—H1AA123.6
C16—C17—C0AA103.9 (6)C17—C0AA—H0AA120.9
C18—C17—C16115.7 (4)C1AA—C0AA—C17118.1 (12)
C18—C17—C20109.1 (5)C1AA—C0AA—H0AA120.9
C18—C17—C0AA140.4 (6)
Symmetry codes: (i) x+2, y+1, z; (ii) x+1, y+1, z.
(RSV-DPE) top
Crystal data top
C14H12O3·2(C6H5N)F(000) = 864
Mr = 410.45Dx = 1.341 Mg m3
Monoclinic, P21/cMo Kα radiation, λ = 0.71073 Å
a = 24.4184 (16) ÅCell parameters from 4351 reflections
b = 6.5303 (4) Åθ = 3.2–23.6°
c = 12.7495 (8) ŵ = 0.09 mm1
β = 90.172 (4)°T = 230 K
V = 2033.0 (2) Å3Block, clear yellowish yellow
Z = 40.19 × 0.11 × 0.08 mm
Data collection top
Bruker APEX-II CCD
diffractometer
3156 reflections with I > 2σ(I)
ω scansRint = 0.068
Absorption correction: multi-scan
SADABS-2014/5 (Bruker,2014/5) was used for absorption correction.
θmax = 27.6°, θmin = 1.7°
Tmin = 0.969, Tmax = 0.991h = 3131
28343 measured reflectionsk = 88
4682 independent reflectionsl = 1616
Refinement top
Refinement on F2Primary atom site location: dual
Least-squares matrix: fullHydrogen site location: mixed
R[F2 > 2σ(F2)] = 0.047H atoms treated by a mixture of independent and constrained refinement
wR(F2) = 0.121 w = 1/[σ2(Fo2) + (0.0548P)2 + 0.0935P]
where P = (Fo2 + 2Fc2)/3
S = 1.04(Δ/σ)max = 0.001
4682 reflectionsΔρmax = 0.16 e Å3
301 parametersΔρmin = 0.27 e Å3
40 restraints
Special details top

Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/UeqOcc. (<1)
O10.12413 (5)0.2452 (2)0.36281 (9)0.0421 (3)
O30.37555 (5)1.05969 (17)0.97733 (10)0.0453 (3)
O20.32749 (5)0.4053 (2)1.10909 (9)0.0454 (3)
N10.44309 (5)0.44638 (19)0.64889 (10)0.0325 (3)
N20.91339 (6)0.0680 (2)0.25515 (11)0.0429 (4)
C200.51344 (6)0.4965 (2)0.95487 (11)0.0284 (3)
H200.5518050.5069810.9581280.034*
C170.48878 (6)0.4740 (2)0.85075 (11)0.0258 (3)
C90.29402 (6)0.6534 (2)0.85800 (11)0.0277 (3)
C180.43265 (6)0.4508 (2)0.83554 (12)0.0301 (4)
H180.4089480.4439420.8933900.036*
C110.32386 (6)0.5454 (2)1.02896 (12)0.0298 (3)
C160.52122 (6)0.4770 (2)0.76107 (12)0.0286 (3)
H160.5594890.4875420.7671840.034*
C10.15489 (6)0.2965 (3)0.44784 (12)0.0314 (4)
C150.49716 (6)0.4644 (2)0.66348 (12)0.0306 (4)
H150.5198700.4686650.6041140.037*
C130.34959 (6)0.8758 (2)0.96586 (12)0.0307 (4)
C120.35084 (6)0.7295 (2)1.04445 (12)0.0294 (3)
H120.3697480.7548701.1074600.035*
C80.26542 (6)0.6158 (3)0.75827 (12)0.0315 (4)
H80.2622970.7268810.7117350.038*
C140.32128 (6)0.8383 (2)0.87318 (12)0.0311 (4)
H140.3205190.9385620.8202930.037*
C40.21512 (6)0.3939 (3)0.62937 (12)0.0315 (4)
C100.29527 (6)0.5057 (2)0.93791 (12)0.0300 (4)
H100.2767360.3806110.9293730.036*
C70.24353 (6)0.4387 (3)0.72785 (12)0.0339 (4)
H70.2467160.3293570.7754050.041*
C50.21042 (6)0.5326 (3)0.54629 (12)0.0346 (4)
H50.2276660.6609000.5513050.042*
C190.41225 (6)0.4381 (2)0.73557 (12)0.0332 (4)
H190.3742120.4226380.7272240.040*
C30.19020 (6)0.2029 (3)0.61646 (12)0.0349 (4)
H3A0.1938770.1043990.6697620.042*
C60.18100 (6)0.4848 (3)0.45722 (13)0.0362 (4)
H60.1785650.5803930.4022820.043*
C20.16026 (6)0.1546 (3)0.52747 (13)0.0347 (4)
H2A0.1436100.0253800.5212770.042*
C250.95751 (7)0.0084 (3)0.30793 (14)0.0460 (5)
H250.9708750.1245900.2961380.055*
C210.89562 (7)0.2574 (3)0.27439 (17)0.0537 (5)
H210.8647750.3044400.2372580.064*
C240.98461 (8)0.1295 (4)0.37847 (16)0.0624 (6)
H241.0161980.0804250.4124990.075*
C230.96535 (10)0.3250 (4)0.39968 (16)0.0710 (8)
C220.91961 (9)0.3866 (4)0.34481 (19)0.0672 (7)
H220.9049030.5177890.3558970.081*
C26A1.00612 (17)0.4094 (6)0.4793 (3)0.0373 (8)0.5
H26A1.0380480.3376210.4980480.045*0.5
C26B0.02241 (14)0.4922 (7)0.5290 (3)0.0390 (8)0.5
H26B0.0452380.3764150.5264660.047*0.5
H30.4005 (8)1.057 (4)1.0295 (16)0.093 (8)*
H10.1161 (10)0.358 (3)0.3271 (18)0.094 (9)*
H20.3148 (10)0.294 (3)1.085 (2)0.111 (10)*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
O10.0441 (7)0.0497 (8)0.0325 (7)0.0037 (6)0.0178 (5)0.0029 (6)
O30.0593 (8)0.0316 (7)0.0450 (8)0.0118 (6)0.0214 (6)0.0033 (6)
O20.0648 (8)0.0389 (7)0.0324 (7)0.0095 (6)0.0156 (6)0.0085 (6)
N10.0404 (8)0.0303 (7)0.0266 (7)0.0062 (6)0.0078 (6)0.0014 (6)
N20.0387 (8)0.0531 (10)0.0371 (9)0.0046 (7)0.0055 (6)0.0084 (7)
C200.0272 (8)0.0300 (8)0.0280 (8)0.0007 (6)0.0071 (6)0.0010 (6)
C170.0296 (7)0.0209 (7)0.0269 (8)0.0019 (6)0.0046 (6)0.0016 (6)
C90.0245 (7)0.0356 (9)0.0229 (8)0.0029 (6)0.0030 (6)0.0032 (7)
C180.0293 (8)0.0338 (9)0.0272 (8)0.0032 (6)0.0012 (6)0.0017 (7)
C110.0318 (8)0.0335 (9)0.0239 (8)0.0025 (7)0.0028 (6)0.0014 (7)
C160.0310 (8)0.0238 (7)0.0310 (9)0.0007 (6)0.0025 (7)0.0014 (6)
C10.0254 (7)0.0434 (10)0.0253 (8)0.0008 (7)0.0060 (6)0.0042 (7)
C150.0381 (9)0.0260 (8)0.0278 (9)0.0036 (6)0.0000 (7)0.0005 (6)
C130.0309 (8)0.0290 (8)0.0321 (9)0.0005 (6)0.0049 (7)0.0032 (7)
C120.0303 (8)0.0339 (9)0.0238 (8)0.0033 (6)0.0070 (6)0.0063 (7)
C80.0286 (8)0.0408 (9)0.0250 (8)0.0003 (7)0.0040 (6)0.0010 (7)
C140.0331 (8)0.0331 (9)0.0271 (8)0.0022 (7)0.0046 (7)0.0017 (7)
C40.0282 (8)0.0415 (9)0.0249 (8)0.0017 (7)0.0034 (6)0.0009 (7)
C100.0296 (8)0.0330 (9)0.0275 (8)0.0035 (6)0.0025 (6)0.0026 (7)
C70.0327 (8)0.0430 (10)0.0260 (8)0.0012 (7)0.0055 (7)0.0012 (7)
C50.0323 (8)0.0414 (9)0.0302 (9)0.0084 (7)0.0058 (7)0.0029 (7)
C190.0307 (8)0.0358 (9)0.0331 (9)0.0040 (7)0.0069 (7)0.0017 (7)
C30.0388 (9)0.0387 (9)0.0272 (9)0.0018 (7)0.0055 (7)0.0051 (7)
C60.0361 (9)0.0449 (10)0.0275 (9)0.0057 (7)0.0068 (7)0.0066 (7)
C20.0343 (8)0.0366 (9)0.0332 (9)0.0045 (7)0.0054 (7)0.0007 (7)
C250.0417 (10)0.0579 (12)0.0383 (11)0.0023 (8)0.0004 (8)0.0011 (9)
C210.0395 (10)0.0544 (12)0.0673 (14)0.0001 (9)0.0021 (9)0.0113 (11)
C240.0505 (12)0.0981 (19)0.0386 (11)0.0295 (12)0.0142 (9)0.0132 (12)
C230.0810 (16)0.098 (2)0.0344 (12)0.0572 (15)0.0127 (11)0.0178 (12)
C220.0662 (14)0.0601 (14)0.0755 (16)0.0204 (11)0.0255 (13)0.0312 (12)
C26A0.0253 (18)0.049 (2)0.038 (2)0.0024 (19)0.0038 (16)0.0102 (19)
C26B0.036 (2)0.043 (2)0.038 (2)0.006 (2)0.0026 (17)0.0062 (19)
Geometric parameters (Å, º) top
O1—C11.3590 (18)C8—H80.9400
O1—H10.887 (16)C8—C71.331 (2)
O3—C131.3657 (19)C14—H140.9400
O3—H30.901 (16)C4—C71.462 (2)
O2—C111.3742 (19)C4—C51.398 (2)
O2—H20.847 (17)C4—C31.397 (2)
N1—C151.3380 (19)C10—H100.9400
N1—C191.340 (2)C7—H70.9400
N2—C251.327 (2)C5—H50.9400
N2—C211.333 (2)C5—C61.378 (2)
C20—C20i1.327 (3)C19—H190.9400
C20—H200.9400C3—H3A0.9400
C20—C171.464 (2)C3—C21.384 (2)
C17—C181.392 (2)C6—H60.9400
C17—C161.393 (2)C2—H2A0.9400
C9—C81.470 (2)C25—H250.9400
C9—C141.392 (2)C25—C241.367 (3)
C9—C101.403 (2)C21—H210.9400
C18—H180.9400C21—C221.363 (3)
C18—C191.370 (2)C24—H240.9400
C11—C121.385 (2)C24—C231.388 (3)
C11—C101.377 (2)C23—C221.376 (3)
C16—H160.9400C23—C26A1.523 (5)
C16—C151.377 (2)C23—C26Bii1.530 (5)
C1—C61.390 (2)C22—H220.9400
C1—C21.380 (2)C26A—C26Aiii1.330 (7)
C15—H150.9400C26A—H26A0.9400
C13—C121.384 (2)C26B—C26Biv1.322 (7)
C13—C141.389 (2)C26B—H26B0.9400
C12—H120.9400
C1—O1—H1108.9 (17)C9—C10—H10120.3
C13—O3—H3112.0 (16)C11—C10—C9119.49 (14)
C11—O2—H2106.1 (19)C11—C10—H10120.3
C15—N1—C19116.47 (13)C8—C7—C4127.82 (16)
C25—N2—C21116.30 (16)C8—C7—H7116.1
C20i—C20—H20117.0C4—C7—H7116.1
C20i—C20—C17125.91 (18)C4—C5—H5119.4
C17—C20—H20117.0C6—C5—C4121.28 (15)
C18—C17—C20122.66 (13)C6—C5—H5119.4
C18—C17—C16116.70 (14)N1—C19—C18124.13 (14)
C16—C17—C20120.63 (13)N1—C19—H19117.9
C14—C9—C8119.41 (14)C18—C19—H19117.9
C14—C9—C10119.08 (14)C4—C3—H3A119.0
C10—C9—C8121.50 (14)C2—C3—C4121.92 (15)
C17—C18—H18120.3C2—C3—H3A119.0
C19—C18—C17119.44 (14)C1—C6—H6119.7
C19—C18—H18120.3C5—C6—C1120.60 (15)
O2—C11—C12116.26 (14)C5—C6—H6119.7
O2—C11—C10122.19 (14)C1—C2—C3119.90 (15)
C10—C11—C12121.56 (14)C1—C2—H2A120.0
C17—C16—H16120.0C3—C2—H2A120.0
C15—C16—C17119.92 (14)N2—C25—H25118.2
C15—C16—H16120.0N2—C25—C24123.7 (2)
O1—C1—C6122.61 (15)C24—C25—H25118.2
O1—C1—C2118.18 (15)N2—C21—H21118.1
C2—C1—C6119.20 (15)N2—C21—C22123.8 (2)
N1—C15—C16123.30 (14)C22—C21—H21118.1
N1—C15—H15118.3C25—C24—H24120.1
C16—C15—H15118.3C25—C24—C23119.8 (2)
O3—C13—C12121.32 (14)C23—C24—H24120.1
O3—C13—C14118.41 (14)C24—C23—C26A104.0 (3)
C12—C13—C14120.27 (14)C24—C23—C26Bii140.2 (3)
C11—C12—H12120.5C22—C23—C24116.41 (19)
C13—C12—C11119.09 (14)C22—C23—C26A139.6 (3)
C13—C12—H12120.5C22—C23—C26Bii103.4 (3)
C9—C8—H8117.0C26A—C23—C26Bii36.40 (16)
C7—C8—C9125.92 (15)C21—C22—C23120.0 (2)
C7—C8—H8117.0C21—C22—H22120.0
C9—C14—H14119.7C23—C22—H22120.0
C13—C14—C9120.51 (15)C23—C26A—H26A122.0
C13—C14—H14119.7C26Aiii—C26A—C23116.1 (5)
C5—C4—C7123.95 (15)C26Aiii—C26A—H26A122.0
C3—C4—C7119.02 (15)C23ii—C26B—H26B122.2
C3—C4—C5117.02 (14)C26Biv—C26B—H26B122.2
Symmetry codes: (i) x+1, y+1, z+2; (ii) x+1, y+1, z+1; (iii) x+2, y+1, z+1; (iv) x, y+1, z+1.
(RSV-1.5DPE-0.5ACE) top
Crystal data top
2(C14H12O3)·3(C12H10N2)·C3H6OZ = 2
Mr = 1061.21F(000) = 1120
Triclinic, P1Dx = 1.243 Mg m3
a = 12.215 (3) ÅMo Kα radiation, λ = 0.71073 Å
b = 15.890 (4) ÅCell parameters from 2202 reflections
c = 17.769 (5) Åθ = 2.3–22.3°
α = 114.901 (6)°µ = 0.08 mm1
β = 92.443 (7)°T = 220 K
γ = 111.284 (6)°Block, colourless
V = 2835.8 (13) Å30.15 × 0.08 × 0.04 mm
Data collection top
Bruker APEX-II CCD
diffractometer
5391 reflections with I > 2σ(I)
φ and ω scansRint = 0.053
Absorption correction: multi-scan
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction. wR2(int) was 0.0714 before and 0.0518 after correction. The Ratio of minimum to maximum transmission is 0.8675. The λ/2 correction factor is Not present.
θmax = 25.7°, θmin = 1.5°
Tmin = 0.647, Tmax = 0.746h = 1414
22595 measured reflectionsk = 1719
10635 independent reflectionsl = 2121
Refinement top
Refinement on F2Primary atom site location: dual
Least-squares matrix: fullHydrogen site location: mixed
R[F2 > 2σ(F2)] = 0.062H atoms treated by a mixture of independent and constrained refinement
wR(F2) = 0.209 w = 1/[σ2(Fo2) + (0.1035P)2]
where P = (Fo2 + 2Fc2)/3
S = 0.96(Δ/σ)max < 0.001
10635 reflectionsΔρmax = 0.71 e Å3
765 parametersΔρmin = 0.25 e Å3
22 restraints
Special details top

Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/UeqOcc. (<1)
O20.19346 (19)0.62541 (15)0.19593 (13)0.0411 (5)
O50.68639 (19)1.13974 (16)0.20609 (14)0.0452 (6)
O10.4451 (2)0.13175 (18)0.38792 (15)0.0531 (6)
O30.1821 (2)0.35277 (17)0.15215 (15)0.0510 (6)
O60.3095 (2)0.85797 (18)0.14610 (17)0.0594 (7)
N30.5514 (2)0.1979 (2)0.12773 (17)0.0422 (6)
N50.2273 (2)0.05724 (19)1.06342 (17)0.0430 (6)
N60.0498 (2)0.30619 (19)0.86170 (16)0.0429 (6)
N40.2638 (2)0.5594 (2)0.06905 (17)0.0448 (7)
O41.0152 (2)0.7448 (2)0.4548 (2)0.0787 (9)
N20.8875 (3)0.5595 (2)0.43974 (18)0.0521 (7)
N10.6474 (2)0.0080 (2)0.55967 (19)0.0493 (7)
C250.1273 (3)0.5368 (2)0.19809 (16)0.0329 (7)
C280.0014 (3)0.3571 (2)0.20437 (17)0.0355 (7)
H280.0422750.2963920.2069730.043*
C260.0033 (3)0.4921 (2)0.17459 (17)0.0352 (7)
H260.0383890.5227630.1573440.042*
C230.1265 (3)0.4023 (2)0.22825 (17)0.0343 (7)
C130.6204 (3)1.0493 (2)0.20420 (17)0.0356 (7)
C240.1901 (3)0.4924 (2)0.22391 (17)0.0354 (7)
H240.2750250.5228690.2383780.043*
C270.0593 (3)0.4011 (2)0.17670 (18)0.0372 (7)
C580.3947 (3)0.3258 (2)0.01060 (19)0.0363 (7)
H580.3642280.2869450.0487580.044*
C480.0488 (3)0.2164 (2)0.93517 (18)0.0351 (7)
C600.3424 (2)0.4615 (2)0.00603 (19)0.0363 (7)
C40.8458 (3)0.8566 (2)0.33738 (18)0.0380 (7)
C590.3873 (3)0.4147 (2)0.04833 (19)0.0390 (7)
H590.4134150.4513380.1080790.047*
C220.1964 (3)0.3591 (2)0.25644 (18)0.0377 (7)
H220.2800200.3884540.2608550.045*
C430.1507 (3)0.0375 (2)0.98422 (18)0.0374 (7)
C140.6806 (3)1.0054 (2)0.23207 (17)0.0390 (7)
H140.7651521.0381340.2513340.047*
C550.4460 (3)0.2827 (2)0.05285 (18)0.0345 (7)
C540.4992 (3)0.3333 (2)0.13970 (18)0.0403 (7)
H540.5002600.3974300.1751050.048*
C180.2312 (3)0.2438 (2)0.30615 (18)0.0375 (7)
C90.6162 (3)0.9125 (2)0.23166 (17)0.0386 (7)
C120.4962 (3)1.0023 (2)0.17616 (18)0.0395 (7)
H120.4556561.0331570.1581530.047*
C110.4312 (3)0.9090 (2)0.17463 (19)0.0415 (8)
C150.3723 (3)0.1654 (2)0.36219 (18)0.0403 (8)
C100.4913 (3)0.8653 (2)0.20281 (18)0.0416 (8)
H100.4472300.8027450.2024770.050*
C210.1565 (3)0.2831 (2)0.27670 (18)0.0397 (7)
H210.0728890.2520430.2716340.048*
C460.1080 (3)0.0843 (2)0.9400 (2)0.0409 (7)
H460.0881520.0494830.8800990.049*
C490.0337 (3)0.3036 (2)0.98402 (19)0.0410 (8)
H490.0573310.3351111.0438040.049*
C470.0952 (3)0.1699 (2)0.97686 (19)0.0371 (7)
H470.1184500.2055321.0367400.045*
C530.5500 (3)0.2888 (2)0.1730 (2)0.0417 (8)
H530.5862690.3247050.2315800.050*
C440.1616 (3)0.0534 (2)0.9376 (2)0.0415 (8)
H440.1429880.0847000.8776570.050*
C170.3530 (3)0.2754 (3)0.3078 (2)0.0481 (8)
H170.3898080.3250700.2902720.058*
C80.6749 (3)0.8628 (2)0.26157 (18)0.0427 (8)
H80.6270070.7952140.2498790.051*
C560.4482 (3)0.1883 (2)0.0060 (2)0.0412 (8)
H560.4138160.1507150.0529180.049*
C10.9594 (3)0.7782 (3)0.4142 (2)0.0487 (8)
C30.7899 (3)0.7572 (2)0.3239 (2)0.0456 (8)
H3A0.7120550.7151230.2881480.055*
C20.8447 (3)0.7178 (3)0.3611 (2)0.0504 (9)
H2A0.8041980.6496610.3505740.061*
C410.2177 (3)0.0299 (2)1.1082 (2)0.0438 (8)
H410.2374030.0594111.1679620.053*
C570.5000 (3)0.1495 (2)0.0452 (2)0.0439 (8)
H570.4990540.0849460.0116910.053*
C360.7069 (3)0.1756 (2)0.5296 (2)0.0454 (8)
C450.1992 (3)0.0972 (2)0.9787 (2)0.0446 (8)
H450.2057370.1587480.9455770.053*
C510.0317 (3)0.2232 (2)0.8140 (2)0.0465 (8)
H510.0525320.1952820.7543680.056*
C500.0156 (3)0.3444 (2)0.9459 (2)0.0450 (8)
H500.0260540.4032750.9811690.054*
C610.3383 (3)0.5547 (2)0.0540 (2)0.0415 (8)
H610.3620940.5867750.1138000.050*
C640.3054 (3)0.4189 (2)0.0817 (2)0.0439 (8)
H640.3063130.3557950.1176040.053*
C50.9614 (3)0.9148 (2)0.3891 (2)0.0474 (8)
H5A1.0027610.9823690.3985350.057*
C520.0153 (3)0.1769 (2)0.84724 (19)0.0455 (8)
H520.0250600.1181530.8106330.055*
O70.5154 (3)0.5483 (2)0.2963 (2)0.1097 (12)
C61.0177 (3)0.8767 (3)0.4271 (2)0.0497 (9)
H6A1.0962120.9182740.4618390.060*
C620.2996 (3)0.6005 (2)0.0149 (2)0.0455 (8)
H620.2985150.6640780.0491860.055*
C420.1811 (3)0.0795 (2)1.0727 (2)0.0433 (8)
H420.1763270.1413331.1076790.052*
C400.6636 (3)0.0778 (3)0.4630 (2)0.0483 (8)
H400.6533410.0663950.4062400.058*
C390.6354 (3)0.0030 (2)0.4808 (2)0.0484 (8)
H390.6062300.0693720.4347930.058*
C70.7880 (3)0.9032 (2)0.30312 (19)0.0445 (8)
H70.8369020.9692190.3117030.053*
C160.4228 (3)0.2369 (2)0.3344 (2)0.0485 (8)
H160.5051070.2595440.3335720.058*
C380.6871 (3)0.1021 (3)0.6225 (2)0.0533 (9)
H380.6946320.1115440.6786470.064*
C190.1809 (3)0.1717 (3)0.3337 (2)0.0504 (9)
H190.0983060.1483420.3335770.061*
C630.2675 (3)0.4689 (2)0.1157 (2)0.0493 (9)
H630.2426120.4382940.1753760.059*
C330.8444 (3)0.4668 (3)0.3734 (2)0.0540 (9)
H330.8450250.4613680.3187180.065*
C310.7937 (3)0.3824 (3)0.4573 (3)0.0566 (9)
C370.7179 (3)0.1861 (3)0.6110 (2)0.0550 (9)
H370.7466380.2514000.6584170.066*
C200.2503 (3)0.1331 (3)0.3617 (2)0.0525 (9)
H200.2140270.0845580.3803930.063*
C320.7995 (3)0.3791 (3)0.3801 (2)0.0575 (9)
H320.7722140.3155680.3308110.069*
C300.8383 (4)0.4800 (3)0.5278 (2)0.0692 (12)
H300.8375980.4873290.5830650.083*
C350.7486 (4)0.2716 (4)0.5263 (3)0.0415 (11)0.75
H350.7818870.3317500.5787350.050*0.75
C290.8825 (4)0.5638 (3)0.5158 (2)0.0646 (11)
H290.9112940.6285440.5638930.078*
C340.7443 (4)0.2828 (4)0.4564 (3)0.0413 (10)0.75
H340.7076280.2236660.4034420.050*0.75
C650.5320 (4)0.6018 (3)0.3707 (3)0.0802 (13)
C670.5210 (5)0.7002 (4)0.4042 (3)0.1053 (17)
H67A0.6005390.7562570.4318870.158*
H67B0.4705820.7035350.4451120.158*
H67C0.4847930.7052730.3575190.158*
C660.5739 (7)0.5764 (4)0.4359 (4)0.143 (2)
H66A0.5083190.5548990.4620260.215*
H66B0.6415220.6363050.4793760.215*
H66C0.5989670.5214780.4083140.215*
C0AA0.7818 (13)0.3225 (9)0.5214 (10)0.048 (4)0.25
H0AA0.8165050.3526210.5798440.058*0.25
C1AA0.7164 (14)0.2303 (10)0.4715 (11)0.053 (4)0.25
H1AA0.6810760.2002770.4132070.064*0.25
H20.144 (3)0.645 (3)0.181 (2)0.063 (11)*
H30.206 (4)0.379 (3)0.126 (2)0.082 (14)*
H60.282 (4)0.884 (3)0.118 (2)0.093 (15)*
H10.410 (4)0.091 (3)0.409 (3)0.105 (17)*
H50.645 (3)1.159 (3)0.182 (2)0.079 (13)*
H40.970 (4)0.686 (3)0.452 (4)0.16 (3)*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
O20.0415 (13)0.0365 (12)0.0490 (13)0.0162 (10)0.0052 (10)0.0239 (11)
O50.0451 (14)0.0394 (13)0.0536 (13)0.0185 (11)0.0002 (10)0.0241 (11)
O10.0485 (15)0.0639 (16)0.0739 (16)0.0293 (13)0.0115 (12)0.0511 (14)
O30.0389 (14)0.0569 (15)0.0742 (16)0.0222 (12)0.0094 (11)0.0440 (14)
O60.0377 (14)0.0602 (15)0.0950 (19)0.0146 (12)0.0007 (12)0.0554 (15)
N30.0407 (16)0.0451 (16)0.0542 (17)0.0201 (13)0.0131 (13)0.0330 (14)
N50.0391 (16)0.0421 (16)0.0526 (16)0.0191 (13)0.0047 (12)0.0253 (14)
N60.0458 (16)0.0439 (16)0.0501 (16)0.0214 (13)0.0103 (12)0.0297 (14)
N40.0398 (16)0.0449 (16)0.0586 (18)0.0199 (13)0.0076 (13)0.0305 (15)
O40.0489 (16)0.080 (2)0.134 (3)0.0219 (15)0.0052 (15)0.080 (2)
N20.063 (2)0.0489 (18)0.0584 (18)0.0265 (15)0.0129 (15)0.0346 (16)
N10.0499 (18)0.0533 (18)0.0624 (19)0.0241 (15)0.0153 (14)0.0403 (17)
C250.0418 (18)0.0300 (16)0.0278 (14)0.0180 (14)0.0043 (12)0.0122 (13)
C280.0411 (18)0.0350 (17)0.0373 (16)0.0194 (14)0.0072 (13)0.0202 (14)
C260.0437 (19)0.0348 (17)0.0347 (15)0.0228 (15)0.0058 (13)0.0177 (14)
C230.0432 (18)0.0365 (17)0.0276 (14)0.0230 (15)0.0046 (13)0.0139 (13)
C130.0461 (19)0.0341 (17)0.0297 (15)0.0216 (15)0.0082 (13)0.0137 (13)
C240.0350 (17)0.0367 (17)0.0360 (16)0.0170 (14)0.0021 (13)0.0172 (14)
C270.0349 (18)0.0424 (18)0.0395 (16)0.0207 (15)0.0076 (13)0.0201 (15)
C580.0363 (17)0.0365 (17)0.0391 (16)0.0161 (14)0.0075 (13)0.0197 (15)
C480.0360 (17)0.0363 (17)0.0415 (17)0.0170 (14)0.0111 (13)0.0239 (15)
C600.0304 (16)0.0379 (18)0.0465 (18)0.0156 (14)0.0123 (13)0.0237 (15)
C40.0408 (18)0.0462 (19)0.0419 (17)0.0271 (16)0.0139 (14)0.0256 (15)
C590.0412 (18)0.0426 (18)0.0421 (17)0.0206 (15)0.0110 (14)0.0249 (15)
C220.0397 (18)0.0385 (17)0.0400 (16)0.0193 (15)0.0049 (13)0.0207 (15)
C430.0362 (17)0.0398 (18)0.0439 (17)0.0182 (14)0.0082 (13)0.0244 (15)
C140.0401 (18)0.0473 (19)0.0355 (16)0.0249 (16)0.0036 (13)0.0195 (15)
C550.0355 (17)0.0364 (17)0.0417 (17)0.0175 (14)0.0145 (13)0.0245 (15)
C540.0464 (19)0.0393 (17)0.0391 (17)0.0223 (15)0.0107 (14)0.0180 (15)
C180.0445 (19)0.0391 (17)0.0405 (16)0.0216 (15)0.0107 (14)0.0252 (15)
C90.051 (2)0.0452 (19)0.0287 (15)0.0302 (16)0.0090 (13)0.0168 (14)
C120.0441 (19)0.0454 (19)0.0398 (17)0.0264 (16)0.0065 (14)0.0233 (15)
C110.0439 (19)0.0434 (19)0.0438 (18)0.0218 (16)0.0054 (14)0.0236 (16)
C150.046 (2)0.0424 (18)0.0425 (17)0.0217 (16)0.0048 (14)0.0267 (15)
C100.049 (2)0.0432 (18)0.0470 (18)0.0254 (16)0.0087 (15)0.0288 (16)
C210.0454 (19)0.0434 (18)0.0370 (16)0.0242 (15)0.0070 (13)0.0202 (15)
C460.0455 (19)0.0411 (18)0.0420 (17)0.0201 (15)0.0093 (14)0.0232 (15)
C490.051 (2)0.0396 (18)0.0378 (16)0.0233 (16)0.0084 (14)0.0192 (15)
C470.0378 (18)0.0412 (18)0.0402 (17)0.0191 (15)0.0091 (13)0.0238 (15)
C530.0433 (19)0.0457 (19)0.0423 (17)0.0206 (16)0.0074 (14)0.0245 (16)
C440.0452 (19)0.0361 (17)0.0454 (18)0.0203 (15)0.0057 (14)0.0187 (15)
C170.046 (2)0.058 (2)0.064 (2)0.0261 (17)0.0165 (16)0.0453 (19)
C80.051 (2)0.0459 (19)0.0432 (17)0.0262 (16)0.0072 (15)0.0269 (16)
C560.0437 (19)0.0380 (18)0.0433 (17)0.0176 (15)0.0098 (14)0.0200 (15)
C10.0398 (19)0.059 (2)0.068 (2)0.0252 (17)0.0068 (16)0.0438 (19)
C30.0368 (18)0.049 (2)0.056 (2)0.0205 (16)0.0052 (15)0.0280 (17)
C20.0377 (19)0.050 (2)0.072 (2)0.0160 (16)0.0018 (16)0.0388 (19)
C410.0442 (19)0.0441 (19)0.0434 (18)0.0195 (16)0.0015 (14)0.0207 (16)
C570.049 (2)0.0381 (18)0.051 (2)0.0232 (16)0.0081 (16)0.0233 (16)
C360.046 (2)0.0418 (17)0.064 (2)0.0235 (16)0.0163 (16)0.0339 (17)
C450.045 (2)0.0361 (18)0.056 (2)0.0212 (15)0.0085 (15)0.0214 (16)
C510.059 (2)0.049 (2)0.0417 (18)0.0290 (18)0.0105 (15)0.0243 (17)
C500.057 (2)0.0412 (19)0.0490 (19)0.0296 (17)0.0158 (16)0.0245 (16)
C610.0429 (19)0.0438 (19)0.0460 (18)0.0236 (15)0.0112 (14)0.0235 (16)
C640.049 (2)0.0389 (18)0.0489 (19)0.0233 (16)0.0083 (15)0.0215 (16)
C50.044 (2)0.0428 (19)0.063 (2)0.0190 (16)0.0089 (16)0.0317 (17)
C520.064 (2)0.0416 (18)0.0428 (18)0.0346 (17)0.0148 (16)0.0197 (16)
O70.111 (3)0.076 (2)0.077 (2)0.0283 (19)0.0119 (19)0.0098 (18)
C60.0386 (19)0.054 (2)0.067 (2)0.0201 (17)0.0026 (16)0.0375 (19)
C620.0425 (19)0.0400 (18)0.061 (2)0.0213 (15)0.0134 (16)0.0261 (17)
C420.051 (2)0.0421 (18)0.0466 (18)0.0272 (16)0.0093 (15)0.0225 (16)
C400.052 (2)0.062 (2)0.0442 (19)0.0278 (18)0.0145 (15)0.0328 (18)
C390.050 (2)0.0410 (19)0.051 (2)0.0202 (16)0.0070 (16)0.0181 (17)
C70.047 (2)0.052 (2)0.0511 (19)0.0277 (17)0.0143 (16)0.0322 (17)
C160.0401 (19)0.058 (2)0.067 (2)0.0225 (17)0.0127 (16)0.0452 (19)
C380.050 (2)0.074 (3)0.0418 (19)0.024 (2)0.0084 (16)0.034 (2)
C190.040 (2)0.062 (2)0.070 (2)0.0235 (17)0.0133 (16)0.047 (2)
C630.058 (2)0.047 (2)0.0447 (19)0.0252 (17)0.0041 (16)0.0221 (17)
C330.066 (2)0.065 (3)0.0430 (19)0.031 (2)0.0107 (17)0.032 (2)
C310.058 (2)0.054 (2)0.087 (3)0.0360 (18)0.032 (2)0.047 (2)
C370.067 (2)0.044 (2)0.046 (2)0.0229 (18)0.0107 (17)0.0148 (17)
C200.043 (2)0.058 (2)0.078 (2)0.0205 (17)0.0151 (17)0.051 (2)
C320.062 (2)0.046 (2)0.060 (2)0.0242 (18)0.0091 (18)0.0190 (19)
C300.110 (4)0.091 (3)0.051 (2)0.064 (3)0.040 (2)0.052 (2)
C350.043 (3)0.031 (2)0.047 (3)0.011 (2)0.009 (2)0.019 (2)
C290.099 (3)0.053 (2)0.049 (2)0.041 (2)0.017 (2)0.0227 (19)
C340.044 (3)0.0375 (19)0.041 (2)0.016 (2)0.007 (2)0.018 (2)
C650.062 (3)0.059 (3)0.086 (3)0.014 (2)0.019 (2)0.016 (3)
C670.105 (4)0.103 (4)0.094 (4)0.065 (3)0.027 (3)0.015 (3)
C660.204 (7)0.108 (4)0.135 (5)0.067 (5)0.059 (5)0.068 (4)
C0AA0.043 (5)0.054 (5)0.041 (5)0.021 (4)0.011 (4)0.015 (4)
C1AA0.055 (6)0.054 (6)0.047 (5)0.022 (4)0.013 (4)0.022 (4)
Geometric parameters (Å, º) top
O2—C251.364 (3)C49—C501.364 (4)
O2—H20.861 (18)C47—H470.9400
O5—C131.353 (4)C53—H530.9400
O5—H50.857 (18)C44—H440.9400
O1—C151.342 (3)C44—C451.365 (4)
O1—H10.878 (19)C17—H170.9400
O3—C271.363 (4)C17—C161.384 (4)
O3—H30.841 (18)C8—H80.9400
O6—C111.356 (4)C8—C71.317 (4)
O6—H60.877 (18)C56—H560.9400
N3—C531.331 (4)C56—C571.367 (4)
N3—C571.326 (4)C1—C21.387 (4)
N5—C411.328 (4)C1—C61.373 (4)
N5—C451.335 (4)C3—H3A0.9400
N6—C511.339 (4)C3—C21.376 (4)
N6—C501.333 (4)C2—H2A0.9400
N4—C621.326 (4)C41—H410.9400
N4—C631.344 (4)C41—C421.367 (4)
O4—C11.345 (4)C57—H570.9400
O4—H40.87 (2)C36—C401.377 (4)
N2—C331.326 (4)C36—C371.380 (5)
N2—C291.329 (4)C36—C351.449 (5)
N1—C391.333 (4)C36—C1AA1.588 (18)
N1—C381.319 (4)C45—H450.9400
C25—C261.374 (4)C51—H510.9400
C25—C241.390 (4)C51—C521.366 (4)
C28—H280.9400C50—H500.9400
C28—C231.386 (4)C61—H610.9400
C28—C271.384 (4)C61—C621.374 (4)
C26—H260.9400C64—H640.9400
C26—C271.386 (4)C64—C631.363 (4)
C23—C241.396 (4)C5—H5A0.9400
C23—C221.460 (4)C5—C61.379 (4)
C13—C141.381 (4)C52—H520.9400
C13—C121.381 (4)O7—C651.189 (5)
C24—H240.9400C6—H6A0.9400
C58—H580.9400C62—H620.9400
C58—C591.324 (4)C42—H420.9400
C58—C551.459 (4)C40—H400.9400
C48—C491.377 (4)C40—C391.377 (4)
C48—C471.463 (4)C39—H390.9400
C48—C521.391 (4)C7—H70.9400
C60—C591.467 (4)C16—H160.9400
C60—C611.384 (4)C38—H380.9400
C60—C641.387 (4)C38—C371.355 (4)
C4—C31.379 (4)C19—H190.9400
C4—C51.385 (4)C19—C201.392 (4)
C4—C71.463 (4)C63—H630.9400
C59—H590.9400C33—H330.9400
C22—H220.9400C33—C321.359 (5)
C22—C211.333 (4)C31—C321.355 (5)
C43—C461.476 (4)C31—C301.402 (5)
C43—C441.390 (4)C31—C341.467 (6)
C43—C421.394 (4)C31—C0AA1.746 (16)
C14—H140.9400C37—H370.9400
C14—C91.395 (4)C20—H200.9400
C55—C541.393 (4)C32—H320.9400
C55—C561.387 (4)C30—H300.9400
C54—H540.9400C30—C291.356 (5)
C54—C531.369 (4)C35—H350.9400
C18—C211.465 (4)C35—C341.328 (5)
C18—C171.380 (4)C29—H290.9400
C18—C191.384 (4)C34—H340.9400
C9—C101.389 (4)C65—C671.480 (6)
C9—C81.468 (4)C65—C661.505 (7)
C12—H120.9400C67—H67A0.9700
C12—C111.393 (4)C67—H67B0.9700
C11—C101.380 (4)C67—H67C0.9700
C15—C161.380 (4)C66—H66A0.9700
C15—C201.386 (4)C66—H66B0.9700
C10—H100.9400C66—H66C0.9700
C21—H210.9400C0AA—H0AA0.9400
C46—H460.9400C0AA—C1AA1.253 (14)
C46—C471.311 (4)C1AA—H1AA0.9400
C49—H490.9400
C25—O2—H2108 (2)C3—C2—C1120.2 (3)
C13—O5—H5113 (3)C3—C2—H2A119.9
C15—O1—H1114 (3)N5—C41—H41117.9
C27—O3—H3108 (3)N5—C41—C42124.1 (3)
C11—O6—H6110 (3)C42—C41—H41117.9
C57—N3—C53116.3 (3)N3—C57—C56123.7 (3)
C41—N5—C45116.7 (3)N3—C57—H57118.2
C50—N6—C51115.8 (3)C56—C57—H57118.2
C62—N4—C63116.5 (3)C40—C36—C37117.1 (3)
C1—O4—H4115 (4)C40—C36—C35128.5 (3)
C33—N2—C29116.3 (3)C40—C36—C1AA95.7 (6)
C38—N1—C39116.5 (3)C37—C36—C35114.3 (3)
O2—C25—C26121.4 (2)C37—C36—C1AA147.1 (6)
O2—C25—C24117.5 (3)N5—C45—C44123.4 (3)
C26—C25—C24121.1 (3)N5—C45—H45118.3
C23—C28—H28119.9C44—C45—H45118.3
C27—C28—H28119.9N6—C51—H51118.2
C27—C28—C23120.2 (3)N6—C51—C52123.6 (3)
C25—C26—H26120.5C52—C51—H51118.2
C25—C26—C27119.0 (3)N6—C50—C49124.1 (3)
C27—C26—H26120.5N6—C50—H50117.9
C28—C23—C24119.2 (3)C49—C50—H50117.9
C28—C23—C22123.1 (3)C60—C61—H61119.7
C24—C23—C22117.7 (3)C62—C61—C60120.5 (3)
O5—C13—C14118.1 (3)C62—C61—H61119.7
O5—C13—C12121.4 (3)C60—C64—H64120.1
C12—C13—C14120.5 (3)C63—C64—C60119.8 (3)
C25—C24—C23119.7 (3)C63—C64—H64120.1
C25—C24—H24120.2C4—C5—H5A119.0
C23—C24—H24120.2C6—C5—C4122.1 (3)
O3—C27—C28118.1 (3)C6—C5—H5A119.0
O3—C27—C26121.1 (3)C48—C52—H52119.9
C28—C27—C26120.8 (3)C51—C52—C48120.1 (3)
C59—C58—H58117.1C51—C52—H52119.9
C59—C58—C55125.9 (3)C1—C6—C5120.1 (3)
C55—C58—H58117.1C1—C6—H6A119.9
C49—C48—C47119.7 (3)C5—C6—H6A119.9
C49—C48—C52116.1 (3)N4—C62—C61123.1 (3)
C52—C48—C47124.2 (3)N4—C62—H62118.4
C61—C60—C59120.1 (3)C61—C62—H62118.4
C61—C60—C64116.2 (3)C43—C42—H42120.4
C64—C60—C59123.7 (3)C41—C42—C43119.3 (3)
C3—C4—C5116.8 (3)C41—C42—H42120.4
C3—C4—C7123.6 (3)C36—C40—H40120.5
C5—C4—C7119.6 (3)C36—C40—C39119.0 (3)
C58—C59—C60126.4 (3)C39—C40—H40120.5
C58—C59—H59116.8N1—C39—C40123.5 (3)
C60—C59—H59116.8N1—C39—H39118.3
C23—C22—H22115.9C40—C39—H39118.3
C21—C22—C23128.1 (3)C4—C7—H7116.4
C21—C22—H22115.9C8—C7—C4127.1 (3)
C44—C43—C46120.2 (3)C8—C7—H7116.4
C44—C43—C42116.5 (3)C15—C16—C17120.3 (3)
C42—C43—C46123.3 (3)C15—C16—H16119.8
C13—C14—H14120.0C17—C16—H16119.8
C13—C14—C9120.0 (3)N1—C38—H38118.0
C9—C14—H14120.0N1—C38—C37124.0 (3)
C54—C55—C58123.5 (3)C37—C38—H38118.0
C56—C55—C58120.4 (3)C18—C19—H19119.3
C56—C55—C54116.1 (3)C18—C19—C20121.3 (3)
C55—C54—H54120.4C20—C19—H19119.3
C53—C54—C55119.3 (3)N4—C63—C64123.9 (3)
C53—C54—H54120.4N4—C63—H63118.1
C17—C18—C21122.7 (3)C64—C63—H63118.1
C17—C18—C19116.9 (3)N2—C33—H33118.1
C19—C18—C21120.5 (3)N2—C33—C32123.7 (3)
C14—C9—C8122.6 (3)C32—C33—H33118.1
C10—C9—C14119.1 (3)C32—C31—C30116.2 (3)
C10—C9—C8118.4 (3)C32—C31—C34115.6 (4)
C13—C12—H12120.1C32—C31—C0AA149.4 (5)
C13—C12—C11119.9 (3)C30—C31—C34128.2 (4)
C11—C12—H12120.1C30—C31—C0AA92.8 (5)
O6—C11—C12122.6 (3)C36—C37—H37120.1
O6—C11—C10117.8 (3)C38—C37—C36119.9 (3)
C10—C11—C12119.6 (3)C38—C37—H37120.1
O1—C15—C16117.5 (3)C15—C20—C19120.9 (3)
O1—C15—C20124.4 (3)C15—C20—H20119.6
C16—C15—C20118.1 (3)C19—C20—H20119.6
C9—C10—H10119.6C33—C32—H32119.7
C11—C10—C9120.9 (3)C31—C32—C33120.6 (3)
C11—C10—H10119.6C31—C32—H32119.7
C22—C21—C18125.9 (3)C31—C30—H30120.2
C22—C21—H21117.1C29—C30—C31119.6 (3)
C18—C21—H21117.1C29—C30—H30120.2
C43—C46—H46117.1C36—C35—H35116.8
C47—C46—C43125.9 (3)C34—C35—C36126.4 (5)
C47—C46—H46117.1C34—C35—H35116.8
C48—C49—H49119.9N2—C29—C30123.6 (3)
C50—C49—C48120.2 (3)N2—C29—H29118.2
C50—C49—H49119.9C30—C29—H29118.2
C48—C47—H47116.4C31—C34—H34118.2
C46—C47—C48127.3 (3)C35—C34—C31123.7 (5)
C46—C47—H47116.4C35—C34—H34118.2
N3—C53—C54124.3 (3)O7—C65—C67122.0 (5)
N3—C53—H53117.8O7—C65—C66121.5 (5)
C54—C53—H53117.8C67—C65—C66116.4 (4)
C43—C44—H44120.0C65—C67—H67A109.5
C45—C44—C43120.1 (3)C65—C67—H67B109.5
C45—C44—H44120.0C65—C67—H67C109.5
C18—C17—H17118.7H67A—C67—H67B109.5
C18—C17—C16122.5 (3)H67A—C67—H67C109.5
C16—C17—H17118.7H67B—C67—H67C109.5
C9—C8—H8116.7C65—C66—H66A109.5
C7—C8—C9126.6 (3)C65—C66—H66B109.5
C7—C8—H8116.7C65—C66—H66C109.5
C55—C56—H56119.8H66A—C66—H66B109.5
C57—C56—C55120.3 (3)H66A—C66—H66C109.5
C57—C56—H56119.8H66B—C66—H66C109.5
O4—C1—C2122.6 (3)C31—C0AA—H0AA128.0
O4—C1—C6118.6 (3)C1AA—C0AA—C31104.0 (14)
C6—C1—C2118.8 (3)C1AA—C0AA—H0AA128.0
C4—C3—H3A119.0C36—C1AA—H1AA128.0
C2—C3—C4122.0 (3)C0AA—C1AA—C36104.0 (15)
C2—C3—H3A119.0C0AA—C1AA—H1AA128.0
C1—C2—H2A119.9
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
O2—H2···N6i0.86 (2)1.88 (2)2.735 (3)172 (3)
O3—H3···N4ii0.84 (2)1.94 (2)2.782 (3)177 (4)
O6—H6···N5iii0.88 (2)1.86 (2)2.739 (3)178 (4)
O1—H1···N1iv0.88 (2)1.79 (2)2.661 (3)169 (4)
O5—H5···N3v0.86 (2)1.88 (2)2.740 (3)179 (4)
O4—H4···N20.87 (2)1.80 (2)2.673 (4)173 (6)
Symmetry codes: (i) x, y+1, z+1; (ii) x, y+1, z; (iii) x, y+1, z1; (iv) x+1, y, z+1; (v) x, y+1, z.
(RSV-1.5DPE-MeOH) top
Crystal data top
C14H12O3·1.5(C12H10N2)·CH4OZ = 2
Mr = 533.61F(000) = 564
Triclinic, P1Dx = 1.266 Mg m3
a = 11.765 (3) ÅMo Kα radiation, λ = 0.71073 Å
b = 11.892 (3) ÅCell parameters from 1641 reflections
c = 12.314 (3) Åθ = 2.3–21.7°
α = 95.213 (7)°µ = 0.08 mm1
β = 111.706 (6)°T = 220 K
γ = 114.134 (6)°Block, clear light colourless
V = 1400.0 (7) Å30.16 × 0.12 × 0.08 mm
Data collection top
Bruker APEX-II CCD
diffractometer
3094 reflections with I > 2σ(I)
φ and ω scansRint = 0.046
Absorption correction: multi-scan
SADABS-2014/5 (Bruker,2014/5) was used for absorption correction. wR2(int) was 0.0704 before and 0.0553 after correction. The Ratio of minimum to maximum transmission is 0.8816. The λ/2 correction factor is 0.00150.
θmax = 27.7°, θmin = 1.9°
Tmin = 0.657, Tmax = 0.746h = 1515
12980 measured reflectionsk = 1515
6409 independent reflectionsl = 1516
Refinement top
Refinement on F2Primary atom site location: dual
Least-squares matrix: fullHydrogen site location: mixed
R[F2 > 2σ(F2)] = 0.064H atoms treated by a mixture of independent and constrained refinement
wR(F2) = 0.219 w = 1/[σ2(Fo2) + (0.1032P)2]
where P = (Fo2 + 2Fc2)/3
S = 0.99(Δ/σ)max < 0.001
6409 reflectionsΔρmax = 0.22 e Å3
390 parametersΔρmin = 0.26 e Å3
162 restraints
Special details top

Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/UeqOcc. (<1)
O10.9399 (2)0.33405 (18)0.03997 (19)0.0661 (5)
O20.4004 (2)0.8436 (2)0.20077 (18)0.0726 (6)
O30.4546 (2)0.6491 (2)0.52574 (19)0.0771 (6)
O40.0972 (2)0.2538 (2)0.1872 (2)0.0812 (7)
N11.2240 (3)0.1087 (2)0.2728 (2)0.0647 (6)
N30.2258 (2)0.1555 (2)0.0886 (2)0.0642 (6)
N20.7056 (2)0.2491 (2)0.4389 (2)0.0666 (6)
C120.4261 (2)0.7490 (2)0.3647 (2)0.0467 (6)
H120.3766820.7822420.3894720.056*
C290.4052 (2)0.0871 (2)0.0339 (2)0.0526 (5)
C130.4754 (3)0.6752 (2)0.4276 (2)0.0536 (6)
C10.8813 (3)0.3891 (2)0.0875 (3)0.0535 (6)
C110.4495 (2)0.7735 (2)0.2659 (2)0.0538 (6)
C171.0452 (3)0.0273 (2)0.3105 (2)0.0559 (6)
C220.8809 (3)0.1544 (3)0.4155 (2)0.0538 (6)
C140.5497 (3)0.6278 (2)0.3922 (3)0.0652 (8)
H140.5835210.5782930.4357620.078*
C230.7404 (3)0.0959 (3)0.3356 (2)0.0596 (7)
H230.7010620.0221250.2711520.072*
C240.6585 (3)0.1456 (3)0.3504 (2)0.0623 (7)
H240.5635360.1038250.2946410.075*
C280.2734 (3)0.0033 (2)0.0111 (3)0.0605 (7)
H280.2415040.0907950.0229350.073*
C200.9472 (3)0.0127 (3)0.3232 (3)0.0607 (7)
H200.8531060.0374290.2662350.073*
C210.9778 (3)0.1112 (3)0.4060 (2)0.0612 (7)
H211.0711870.1590690.4653220.073*
C60.8835 (3)0.3850 (3)0.1995 (3)0.0628 (7)
H60.9271420.3438240.2472100.075*
C90.5747 (3)0.6520 (3)0.2943 (3)0.0728 (9)
C160.9955 (3)0.1391 (3)0.2225 (3)0.0659 (7)
H160.8991750.1901050.1728940.079*
C260.9296 (3)0.2608 (3)0.5086 (3)0.0677 (8)
H261.0238850.3039960.5662110.081*
C100.5251 (3)0.7271 (3)0.2319 (3)0.0696 (8)
H100.5433340.7462730.1657880.084*
C300.4422 (3)0.2135 (3)0.0822 (3)0.0672 (8)
H300.5294810.2799560.0970320.081*
C151.0867 (3)0.1755 (3)0.2075 (3)0.0655 (7)
H151.0497550.2522120.1475230.079*
C270.1890 (3)0.0341 (3)0.0381 (3)0.0673 (8)
H270.0991410.0299540.0198490.081*
C310.3520 (3)0.2418 (3)0.1083 (3)0.0710 (8)
H310.3814450.3286220.1426220.085*
C191.2716 (3)0.0027 (3)0.3593 (3)0.0684 (8)
H191.3683890.0454340.4082200.082*
C20.8167 (3)0.4505 (2)0.0196 (3)0.0697 (8)
H2A0.8140920.4537570.0572000.084*
C181.1887 (3)0.0404 (3)0.3813 (3)0.0669 (8)
H181.2286390.1156600.4442450.080*
C250.8405 (3)0.3032 (3)0.5168 (3)0.0772 (9)
H250.8767300.3754640.5818310.093*
C50.8203 (3)0.4427 (3)0.2405 (3)0.0851 (10)
H50.8214920.4389290.3167710.102*
C30.7564 (3)0.5065 (3)0.0649 (4)0.0905 (12)
H3A0.7130790.5479490.0172280.109*
C40.7554 (3)0.5059 (3)0.1750 (5)0.1021 (15)
C330.2080 (4)0.3504 (4)0.2933 (3)0.1029 (12)
H33A0.2458990.4304820.2734120.154*
H33B0.2800140.3259210.3273270.154*
H33C0.1745370.3617100.3524640.154*
C8A0.6527 (5)0.5815 (6)0.2804 (5)0.0430 (12)0.5
H8A0.6838010.5423620.3395440.052*0.5
C7A0.6764 (5)0.5759 (5)0.1823 (5)0.0423 (11)0.5
H7A0.6454130.6136430.1217500.051*0.5
C7B0.6993 (6)0.5456 (5)0.2613 (6)0.0533 (13)0.5
H7B0.7061270.5205300.3327460.064*0.5
C8B0.6424 (5)0.6171 (5)0.2232 (7)0.0511 (13)0.5
H8B0.6433220.6456240.1546440.061*0.5
C320.5048 (3)0.0573 (2)0.0117 (2)0.0526 (5)
H320.5832520.1266040.0142760.063*
H20.344 (3)0.856 (3)0.225 (3)0.093 (11)*
H30.403 (3)0.683 (3)0.533 (3)0.096 (11)*
H40.130 (3)0.217 (3)0.150 (3)0.103 (12)*
H10.988 (3)0.303 (3)0.087 (3)0.102 (13)*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
O10.0731 (13)0.0676 (12)0.0774 (14)0.0448 (11)0.0424 (11)0.0134 (11)
O20.0751 (14)0.0919 (15)0.0731 (13)0.0450 (13)0.0461 (12)0.0388 (12)
O30.0972 (16)0.0929 (15)0.0792 (14)0.0699 (14)0.0451 (13)0.0438 (12)
O40.0607 (13)0.0718 (14)0.0984 (17)0.0394 (12)0.0196 (13)0.0025 (13)
N10.0649 (16)0.0653 (15)0.0674 (15)0.0362 (13)0.0277 (13)0.0178 (13)
N30.0509 (14)0.0621 (15)0.0760 (16)0.0303 (12)0.0207 (12)0.0217 (13)
N20.0616 (16)0.0880 (17)0.0562 (14)0.0379 (14)0.0312 (13)0.0155 (14)
C120.0427 (13)0.0491 (13)0.0502 (14)0.0246 (12)0.0211 (11)0.0075 (11)
C290.0425 (10)0.0566 (11)0.0489 (10)0.0168 (9)0.0177 (8)0.0184 (9)
C130.0491 (15)0.0547 (15)0.0574 (16)0.0305 (13)0.0192 (13)0.0098 (13)
C10.0446 (14)0.0382 (13)0.0715 (18)0.0164 (12)0.0272 (13)0.0021 (12)
C110.0416 (14)0.0580 (15)0.0559 (16)0.0197 (13)0.0223 (12)0.0088 (13)
C170.0558 (16)0.0553 (15)0.0549 (16)0.0278 (14)0.0219 (14)0.0149 (13)
C220.0544 (16)0.0647 (16)0.0443 (14)0.0282 (14)0.0239 (13)0.0173 (13)
C140.0449 (15)0.0539 (16)0.090 (2)0.0299 (14)0.0208 (15)0.0025 (15)
C230.0610 (18)0.0647 (16)0.0488 (15)0.0284 (15)0.0235 (14)0.0097 (13)
C240.0521 (16)0.082 (2)0.0532 (16)0.0317 (16)0.0243 (14)0.0172 (16)
C280.0486 (15)0.0473 (14)0.0783 (19)0.0198 (13)0.0247 (14)0.0176 (14)
C200.0543 (16)0.0621 (17)0.0569 (16)0.0254 (14)0.0198 (13)0.0136 (14)
C210.0554 (16)0.0681 (17)0.0535 (16)0.0260 (15)0.0228 (14)0.0126 (15)
C60.0574 (16)0.0595 (16)0.0730 (19)0.0242 (14)0.0368 (15)0.0106 (14)
C90.0334 (14)0.0606 (17)0.096 (2)0.0124 (13)0.0227 (16)0.0214 (17)
C160.0548 (17)0.0649 (18)0.0615 (17)0.0246 (15)0.0168 (14)0.0071 (15)
C260.0544 (17)0.081 (2)0.0549 (16)0.0275 (16)0.0213 (14)0.0013 (15)
C100.0478 (16)0.0774 (19)0.0705 (19)0.0152 (15)0.0358 (15)0.0037 (16)
C300.0464 (16)0.0509 (16)0.083 (2)0.0121 (13)0.0215 (15)0.0143 (15)
C150.068 (2)0.0623 (17)0.0594 (17)0.0343 (16)0.0209 (15)0.0080 (14)
C270.0448 (15)0.0561 (17)0.094 (2)0.0205 (14)0.0273 (15)0.0269 (16)
C310.0581 (18)0.0520 (16)0.089 (2)0.0246 (15)0.0221 (16)0.0153 (16)
C190.0540 (17)0.0654 (18)0.0710 (19)0.0269 (15)0.0183 (15)0.0061 (16)
C20.0602 (17)0.0515 (15)0.095 (2)0.0275 (15)0.0317 (17)0.0175 (16)
C180.0634 (19)0.0576 (17)0.0688 (18)0.0282 (15)0.0227 (16)0.0044 (15)
C250.068 (2)0.092 (2)0.0655 (19)0.0363 (19)0.0311 (17)0.0005 (17)
C50.0610 (19)0.076 (2)0.095 (2)0.0066 (17)0.0516 (19)0.0194 (19)
C30.0524 (18)0.0473 (17)0.162 (4)0.0284 (15)0.039 (2)0.002 (2)
C40.0423 (17)0.0515 (18)0.179 (4)0.0044 (15)0.053 (2)0.037 (2)
C330.072 (2)0.104 (3)0.095 (3)0.041 (2)0.008 (2)0.001 (2)
C8A0.035 (3)0.041 (3)0.053 (3)0.025 (2)0.013 (3)0.011 (3)
C7A0.038 (3)0.035 (2)0.056 (3)0.019 (2)0.021 (2)0.011 (2)
C7B0.048 (3)0.049 (3)0.058 (4)0.024 (3)0.019 (3)0.012 (3)
C8B0.042 (3)0.048 (3)0.061 (4)0.020 (3)0.024 (3)0.012 (3)
C320.0425 (10)0.0566 (11)0.0489 (10)0.0168 (9)0.0177 (8)0.0184 (9)
Geometric parameters (Å, º) top
O1—C11.358 (3)C21—H210.9400
O1—H10.873 (18)C6—H60.9400
O2—C111.358 (3)C6—C51.382 (4)
O2—H20.879 (17)C9—C101.396 (4)
O3—C131.357 (3)C9—C8A1.514 (6)
O3—H30.881 (17)C9—C8B1.515 (7)
O4—C331.404 (4)C16—H160.9400
O4—H40.886 (18)C16—C151.373 (4)
N1—C151.327 (4)C26—H260.9400
N1—C191.331 (4)C26—C251.366 (4)
N3—C271.337 (3)C10—H100.9400
N3—C311.326 (3)C30—H300.9400
N2—C241.327 (3)C30—C311.368 (4)
N2—C251.334 (4)C15—H150.9400
C12—H120.9400C27—H270.9400
C12—C131.384 (3)C31—H310.9400
C12—C111.374 (3)C19—H190.9400
C29—C281.378 (3)C19—C181.367 (4)
C29—C301.383 (4)C2—H2A0.9400
C29—C321.460 (4)C2—C31.368 (4)
C13—C141.383 (3)C18—H180.9400
C1—C61.376 (4)C25—H250.9400
C1—C21.380 (4)C5—H50.9400
C11—C101.381 (4)C5—C41.386 (5)
C17—C201.466 (4)C3—H3A0.9400
C17—C161.385 (4)C3—C41.361 (6)
C17—C181.389 (4)C4—C7A1.499 (6)
C22—C231.384 (4)C4—C7B1.571 (7)
C22—C211.464 (4)C33—H33A0.9700
C22—C261.378 (4)C33—H33B0.9700
C14—H140.9400C33—H33C0.9700
C14—C91.370 (4)C8A—H8A0.9400
C23—H230.9400C8A—C7A1.339 (7)
C23—C241.374 (4)C7A—H7A0.9400
C24—H240.9400C7B—H7B0.9400
C28—H280.9400C7B—C8B1.302 (7)
C28—C271.368 (4)C8B—H8B0.9400
C20—H200.9400C32—C32i1.316 (5)
C20—C211.307 (4)C32—H320.9400
C1—O1—H1117 (2)C11—C10—C9120.9 (3)
C11—O2—H2109 (2)C11—C10—H10119.6
C13—O3—H3106 (2)C9—C10—H10119.6
C33—O4—H4109 (2)C29—C30—H30120.0
C15—N1—C19116.1 (2)C31—C30—C29120.1 (3)
C31—N3—C27114.9 (2)C31—C30—H30120.0
C24—N2—C25115.6 (2)N1—C15—C16123.9 (3)
C13—C12—H12120.1N1—C15—H15118.1
C11—C12—H12120.1C16—C15—H15118.1
C11—C12—C13119.7 (2)N3—C27—C28124.4 (2)
C28—C29—C30115.9 (2)N3—C27—H27117.8
C28—C29—C32124.5 (2)C28—C27—H27117.8
C30—C29—C32119.7 (2)N3—C31—C30124.6 (3)
O3—C13—C12121.5 (2)N3—C31—H31117.7
O3—C13—C14118.4 (2)C30—C31—H31117.7
C14—C13—C12120.1 (2)N1—C19—H19117.9
O1—C1—C6122.5 (2)N1—C19—C18124.1 (3)
O1—C1—C2118.2 (3)C18—C19—H19117.9
C6—C1—C2119.3 (2)C1—C2—H2A120.2
O2—C11—C12121.3 (2)C3—C2—C1119.5 (3)
O2—C11—C10118.9 (2)C3—C2—H2A120.2
C12—C11—C10119.8 (3)C17—C18—H18120.1
C16—C17—C20119.6 (3)C19—C18—C17119.9 (3)
C16—C17—C18116.0 (3)C19—C18—H18120.1
C18—C17—C20124.4 (3)N2—C25—C26124.4 (3)
C23—C22—C21124.4 (3)N2—C25—H25117.8
C26—C22—C23116.2 (2)C26—C25—H25117.8
C26—C22—C21119.4 (3)C6—C5—H5118.3
C13—C14—H14119.6C6—C5—C4123.5 (3)
C9—C14—C13120.9 (3)C4—C5—H5118.3
C9—C14—H14119.6C2—C3—H3A118.1
C22—C23—H23120.0C4—C3—C2123.9 (3)
C24—C23—C22120.1 (3)C4—C3—H3A118.1
C24—C23—H23120.0C5—C4—C7A140.9 (5)
N2—C24—C23123.8 (3)C5—C4—C7B101.1 (4)
N2—C24—H24118.1C3—C4—C5115.1 (3)
C23—C24—H24118.1C3—C4—C7A103.9 (4)
C29—C28—H28120.0C3—C4—C7B143.7 (4)
C27—C28—C29120.0 (2)O4—C33—H33A109.5
C27—C28—H28120.0O4—C33—H33B109.5
C17—C20—H20116.8O4—C33—H33C109.5
C21—C20—C17126.4 (3)H33A—C33—H33B109.5
C21—C20—H20116.8H33A—C33—H33C109.5
C22—C21—H21116.8H33B—C33—H33C109.5
C20—C21—C22126.4 (3)C9—C8A—H8A120.7
C20—C21—H21116.8C7A—C8A—C9118.7 (6)
C1—C6—H6120.7C7A—C8A—H8A120.7
C1—C6—C5118.7 (3)C4—C7A—H7A122.1
C5—C6—H6120.7C8A—C7A—C4115.9 (6)
C14—C9—C10118.6 (2)C8A—C7A—H7A122.1
C14—C9—C8A105.9 (4)C4—C7B—H7B123.7
C14—C9—C8B138.5 (4)C8B—C7B—C4112.7 (6)
C10—C9—C8A135.6 (4)C8B—C7B—H7B123.7
C10—C9—C8B102.9 (4)C9—C8B—H8B121.5
C17—C16—H16120.0C7B—C8B—C9116.9 (7)
C15—C16—C17120.0 (3)C7B—C8B—H8B121.5
C15—C16—H16120.0C29—C32—H32116.9
C22—C26—H26120.1C32i—C32—C29126.3 (3)
C25—C26—C22119.8 (3)C32i—C32—H32116.9
C25—C26—H26120.1
Symmetry code: (i) x+1, y, z.
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
O2—H2···N1ii0.88 (2)1.89 (2)2.766 (3)177 (3)
O3—H3···N2iii0.88 (2)1.88 (2)2.754 (3)175 (3)
O4—H4···N30.89 (2)1.89 (2)2.770 (3)172 (3)
O1—H1···O4iv0.87 (2)1.76 (2)2.626 (3)175 (3)
Symmetry codes: (ii) x1, y+1, z; (iii) x+1, y+1, z+1; (iv) x+1, y, z.
(RSV-2AZPY) top
Crystal data top
C14H12O3·2(C10H8N4)F(000) = 2496
Mr = 596.64Dx = 1.337 Mg m3
Monoclinic, C2/cMo Kα radiation, λ = 0.71073 Å
a = 17.606 (6) ÅCell parameters from 1043 reflections
b = 7.969 (3) Åθ = 2.4–20.8°
c = 42.568 (14) ŵ = 0.09 mm1
β = 97.006 (7)°T = 220 K
V = 5928 (3) Å3Needle, clear orangish orange
Z = 80.2 × 0.08 × 0.02 mm
Data collection top
Bruker APEX-II CCD
diffractometer
2609 reflections with I > 2σ(I)
φ and ω scansRint = 0.091
Absorption correction: multi-scan
SADABS-2014/5 (Bruker,2014/5) was used for absorption correction. wR2(int) was 0.0914 before and 0.0560 after correction. The Ratio of minimum to maximum transmission is 0.7415. The λ/2 correction factor is 0.00150.
θmax = 25.0°, θmin = 1.9°
Tmin = 0.553, Tmax = 0.745h = 2015
15154 measured reflectionsk = 89
5148 independent reflectionsl = 5050
Refinement top
Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullHydrogen site location: mixed
R[F2 > 2σ(F2)] = 0.073H atoms treated by a mixture of independent and constrained refinement
wR(F2) = 0.241 w = 1/[σ2(Fo2) + (0.1155P)2]
where P = (Fo2 + 2Fc2)/3
S = 1.02(Δ/σ)max < 0.001
5148 reflectionsΔρmax = 0.35 e Å3
418 parametersΔρmin = 0.31 e Å3
17 restraints
Special details top

Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
O30.36308 (17)0.0842 (4)0.54829 (7)0.0372 (8)
O20.3623 (2)0.4783 (5)0.50795 (7)0.0474 (10)
O10.3766 (2)0.8777 (5)0.74604 (7)0.0503 (10)
N20.0715 (2)0.4559 (5)0.62856 (7)0.0358 (10)
N10.1093 (2)0.1935 (5)0.54587 (7)0.0348 (10)
N30.1286 (2)0.5238 (5)0.64369 (8)0.0344 (10)
N80.6353 (2)0.1538 (5)0.51584 (8)0.0383 (10)
N50.6369 (2)0.7075 (5)0.70086 (8)0.0392 (10)
N60.6680 (2)0.4601 (5)0.61557 (8)0.0415 (10)
N40.0964 (2)0.7684 (5)0.72896 (8)0.0440 (11)
N70.6115 (2)0.3850 (6)0.60305 (8)0.0446 (10)
C130.3639 (2)0.0842 (6)0.55253 (9)0.0271 (10)
C200.1132 (2)0.6048 (6)0.67213 (9)0.0317 (11)
C170.0881 (2)0.3722 (6)0.60029 (9)0.0330 (11)
C90.3708 (2)0.3206 (6)0.58855 (9)0.0293 (11)
C100.3679 (2)0.4286 (6)0.56282 (9)0.0299 (11)
H100.3693350.5453130.5660580.036*
C30.3654 (3)0.7938 (6)0.66238 (9)0.0355 (12)
H3A0.3599740.8565480.6435490.043*
C40.3697 (2)0.6221 (6)0.66043 (9)0.0315 (11)
C50.3786 (2)0.5307 (6)0.68905 (9)0.0315 (11)
H50.3829080.4132000.6886290.038*
C10.3754 (2)0.7888 (6)0.71915 (9)0.0334 (11)
C140.3703 (2)0.1503 (6)0.58320 (9)0.0311 (11)
H140.3744020.0765820.6005660.037*
C160.0277 (2)0.2909 (6)0.58279 (9)0.0352 (12)
H160.0214370.2938470.5892630.042*
C80.3753 (2)0.3845 (7)0.62127 (9)0.0352 (12)
H80.3857100.3065240.6378080.042*
C300.6255 (3)0.3042 (6)0.57368 (9)0.0353 (11)
C110.3630 (2)0.3643 (6)0.53232 (9)0.0308 (11)
C60.3809 (2)0.6139 (7)0.71785 (9)0.0373 (12)
H60.3861790.5516850.7367430.045*
C120.3591 (2)0.1948 (6)0.52689 (9)0.0358 (12)
H120.3533510.1531930.5060670.043*
C260.5816 (3)0.5471 (6)0.65655 (10)0.0372 (12)
H260.5382950.4946010.6457300.045*
C270.6519 (3)0.5434 (6)0.64450 (10)0.0378 (11)
C190.1676 (2)0.2716 (6)0.56321 (9)0.0378 (12)
H190.2164690.2637600.5565740.045*
C20.3686 (2)0.8786 (6)0.69108 (9)0.0381 (12)
H2A0.3662580.9964220.6914270.046*
C240.1747 (2)0.6795 (6)0.68970 (9)0.0356 (11)
H240.2234950.6760290.6828540.043*
C70.3656 (2)0.5455 (6)0.62923 (9)0.0362 (12)
H70.3544980.6196970.6121120.043*
C310.5608 (2)0.2489 (6)0.55532 (10)0.0383 (12)
H310.5123590.2609940.5622500.046*
C230.1638 (3)0.7608 (6)0.71786 (10)0.0405 (12)
H230.2061370.8126240.7295570.049*
C250.5775 (3)0.6296 (7)0.68467 (10)0.0432 (13)
H250.5303270.6312330.6929020.052*
C330.6988 (3)0.2035 (6)0.53452 (10)0.0414 (12)
H330.7468300.1847330.5275910.050*
C320.5681 (3)0.1752 (6)0.52652 (10)0.0404 (12)
H320.5236360.1385190.5139090.049*
C340.6961 (2)0.2802 (6)0.56318 (9)0.0375 (12)
H340.7412440.3157320.5754610.045*
C180.1600 (2)0.3622 (6)0.59009 (9)0.0356 (12)
H180.2023470.4161340.6013240.043*
C280.7121 (3)0.6266 (7)0.66048 (10)0.0451 (13)
H280.7594850.6301920.6524440.054*
C150.0402 (2)0.2068 (6)0.55618 (9)0.0381 (12)
H150.0018360.1549220.5442610.046*
C210.0423 (3)0.6096 (7)0.68351 (10)0.0450 (13)
H210.0010070.5590190.6722740.054*
C220.0377 (3)0.6909 (6)0.71173 (10)0.0439 (13)
H220.0099700.6923670.7195170.053*
C290.7030 (3)0.7054 (7)0.68853 (10)0.0427 (13)
H290.7453490.7604750.6995380.051*
H10.373 (3)0.811 (5)0.7622 (8)0.055 (16)*
H30.361 (2)0.108 (6)0.5289 (5)0.043 (14)*
H20.363 (3)0.427 (6)0.4909 (8)0.066 (18)*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
O30.0448 (19)0.036 (2)0.0305 (18)0.0038 (16)0.0048 (14)0.0017 (16)
O20.082 (3)0.039 (2)0.0222 (17)0.0000 (19)0.0119 (16)0.0027 (16)
O10.086 (3)0.045 (2)0.0217 (17)0.007 (2)0.0132 (16)0.0063 (17)
N20.033 (2)0.049 (3)0.0258 (19)0.0013 (19)0.0037 (15)0.0079 (18)
N10.041 (2)0.039 (3)0.0253 (19)0.0013 (19)0.0081 (16)0.0004 (18)
N30.039 (2)0.033 (3)0.033 (2)0.0066 (18)0.0083 (16)0.0032 (18)
N80.043 (2)0.038 (3)0.034 (2)0.0036 (19)0.0054 (17)0.0040 (18)
N50.049 (2)0.040 (3)0.029 (2)0.000 (2)0.0044 (17)0.0030 (19)
N60.044 (2)0.046 (3)0.0347 (19)0.003 (2)0.0036 (17)0.0048 (18)
N40.050 (3)0.048 (3)0.034 (2)0.002 (2)0.0090 (19)0.002 (2)
N70.050 (2)0.049 (3)0.0348 (19)0.004 (2)0.0031 (17)0.0003 (19)
C130.028 (2)0.025 (3)0.030 (2)0.0002 (19)0.0069 (17)0.006 (2)
C200.031 (2)0.037 (3)0.028 (2)0.002 (2)0.0060 (18)0.000 (2)
C170.033 (2)0.044 (3)0.023 (2)0.000 (2)0.0039 (18)0.000 (2)
C90.023 (2)0.036 (3)0.029 (2)0.000 (2)0.0031 (17)0.004 (2)
C100.035 (2)0.029 (3)0.026 (2)0.003 (2)0.0061 (18)0.004 (2)
C30.050 (3)0.036 (3)0.021 (2)0.005 (2)0.0080 (19)0.000 (2)
C40.029 (2)0.042 (3)0.024 (2)0.001 (2)0.0054 (17)0.001 (2)
C50.033 (2)0.029 (3)0.033 (2)0.002 (2)0.0083 (19)0.001 (2)
C10.039 (3)0.033 (3)0.027 (2)0.005 (2)0.0040 (18)0.001 (2)
C140.034 (2)0.032 (3)0.028 (2)0.003 (2)0.0054 (18)0.002 (2)
C160.031 (2)0.049 (3)0.028 (2)0.003 (2)0.0087 (18)0.003 (2)
C80.034 (3)0.047 (4)0.025 (2)0.001 (2)0.0043 (18)0.001 (2)
C300.044 (2)0.035 (3)0.029 (2)0.003 (2)0.0115 (19)0.0003 (19)
C110.037 (3)0.027 (3)0.028 (2)0.003 (2)0.0071 (18)0.001 (2)
C60.036 (3)0.052 (4)0.024 (2)0.002 (2)0.0057 (18)0.002 (2)
C120.036 (3)0.050 (4)0.022 (2)0.008 (2)0.0041 (18)0.006 (2)
C260.039 (3)0.037 (3)0.033 (2)0.005 (2)0.005 (2)0.005 (2)
C270.049 (3)0.038 (3)0.027 (2)0.004 (2)0.0078 (19)0.001 (2)
C190.034 (3)0.053 (4)0.028 (2)0.002 (2)0.0077 (19)0.003 (2)
C20.049 (3)0.039 (3)0.027 (2)0.006 (2)0.0056 (19)0.000 (2)
C240.036 (3)0.037 (3)0.035 (2)0.003 (2)0.0075 (19)0.004 (2)
C70.037 (3)0.046 (4)0.026 (2)0.002 (2)0.0028 (19)0.004 (2)
C310.033 (3)0.045 (3)0.038 (3)0.001 (2)0.007 (2)0.006 (2)
C230.041 (3)0.044 (3)0.035 (3)0.001 (2)0.002 (2)0.007 (2)
C250.037 (3)0.060 (4)0.034 (3)0.006 (3)0.008 (2)0.001 (3)
C330.039 (3)0.049 (4)0.037 (3)0.004 (2)0.006 (2)0.002 (2)
C320.036 (3)0.047 (4)0.037 (3)0.009 (2)0.001 (2)0.008 (2)
C340.037 (3)0.047 (3)0.028 (2)0.009 (2)0.0020 (19)0.001 (2)
C180.033 (2)0.045 (3)0.029 (2)0.004 (2)0.0051 (18)0.002 (2)
C280.036 (3)0.064 (4)0.036 (3)0.004 (3)0.008 (2)0.007 (3)
C150.034 (3)0.050 (4)0.030 (2)0.010 (2)0.0016 (19)0.005 (2)
C210.039 (3)0.064 (4)0.032 (2)0.006 (3)0.004 (2)0.011 (3)
C220.041 (3)0.051 (4)0.042 (3)0.002 (3)0.012 (2)0.004 (3)
C290.041 (3)0.051 (4)0.036 (3)0.007 (3)0.000 (2)0.000 (2)
Geometric parameters (Å, º) top
O3—C131.354 (5)C1—C61.399 (7)
O3—H30.846 (19)C1—C21.385 (6)
O2—C111.378 (5)C14—H140.9400
O2—H20.833 (19)C16—H160.9400
O1—C11.344 (5)C16—C151.357 (6)
O1—H10.878 (19)C8—H80.9400
N2—N31.249 (5)C8—C71.343 (7)
N2—C171.437 (5)C30—C311.374 (6)
N1—C191.342 (6)C30—C341.385 (6)
N1—C151.347 (5)C11—C121.371 (7)
N3—C201.426 (5)C6—H60.9400
N8—C331.351 (5)C12—H120.9400
N8—C321.329 (5)C26—H260.9400
N5—C251.333 (6)C26—C271.397 (6)
N5—C291.334 (6)C26—C251.376 (6)
N6—N71.224 (5)C27—C281.360 (6)
N6—C271.457 (6)C19—H190.9400
N4—C231.331 (6)C19—C181.374 (6)
N4—C221.342 (6)C2—H2A0.9400
N7—C301.454 (5)C24—H240.9400
C13—C141.400 (5)C24—C231.396 (6)
C13—C121.397 (6)C7—H70.9400
C20—C241.374 (6)C31—H310.9400
C20—C211.395 (6)C31—C321.379 (6)
C17—C161.382 (6)C23—H230.9400
C17—C181.390 (6)C25—H250.9400
C9—C101.389 (6)C33—H330.9400
C9—C141.376 (6)C33—C341.371 (6)
C9—C81.476 (6)C32—H320.9400
C10—H100.9400C34—H340.9400
C10—C111.389 (5)C18—H180.9400
C3—H3A0.9400C28—H280.9400
C3—C41.373 (7)C28—C291.376 (6)
C3—C21.391 (6)C15—H150.9400
C4—C51.411 (6)C21—H210.9400
C4—C71.456 (6)C21—C221.376 (6)
C5—H50.9400C22—H220.9400
C5—C61.390 (6)C29—H290.9400
C13—O3—H3111 (3)C11—C12—C13119.5 (4)
C11—O2—H2110 (4)C11—C12—H12120.2
C1—O1—H1110 (3)C27—C26—H26120.9
N3—N2—C17113.6 (3)C25—C26—H26120.9
C19—N1—C15116.4 (4)C25—C26—C27118.2 (4)
N2—N3—C20114.2 (3)C26—C27—N6126.3 (4)
C32—N8—C33118.0 (4)C28—C27—N6115.2 (4)
C25—N5—C29117.2 (4)C28—C27—C26118.5 (4)
N7—N6—C27111.1 (4)N1—C19—H19118.1
C23—N4—C22116.4 (4)N1—C19—C18123.8 (4)
N6—N7—C30112.2 (4)C18—C19—H19118.1
O3—C13—C14119.7 (4)C3—C2—H2A120.1
O3—C13—C12121.5 (4)C1—C2—C3119.8 (5)
C12—C13—C14118.8 (4)C1—C2—H2A120.1
C24—C20—N3116.1 (4)C20—C24—H24120.5
C24—C20—C21118.6 (4)C20—C24—C23119.1 (4)
C21—C20—N3125.3 (4)C23—C24—H24120.5
C16—C17—N2116.6 (4)C4—C7—H7115.2
C16—C17—C18118.3 (4)C8—C7—C4129.6 (4)
C18—C17—N2125.0 (4)C8—C7—H7115.2
C10—C9—C8121.5 (4)C30—C31—H31120.6
C14—C9—C10118.8 (4)C30—C31—C32118.8 (4)
C14—C9—C8119.7 (4)C32—C31—H31120.6
C9—C10—H10120.0N4—C23—C24123.3 (4)
C11—C10—C9120.1 (4)N4—C23—H23118.4
C11—C10—H10120.0C24—C23—H23118.4
C4—C3—H3A118.6N5—C25—C26123.5 (4)
C4—C3—C2122.7 (4)N5—C25—H25118.3
C2—C3—H3A118.6C26—C25—H25118.3
C3—C4—C5117.6 (4)N8—C33—H33118.7
C3—C4—C7118.4 (4)N8—C33—C34122.6 (4)
C5—C4—C7124.0 (5)C34—C33—H33118.7
C4—C5—H5119.9N8—C32—C31122.8 (4)
C6—C5—C4120.2 (5)N8—C32—H32118.6
C6—C5—H5119.9C31—C32—H32118.6
O1—C1—C6124.4 (4)C30—C34—H34120.7
O1—C1—C2116.9 (4)C33—C34—C30118.6 (4)
C2—C1—C6118.7 (4)C33—C34—H34120.7
C13—C14—H14119.2C17—C18—H18120.8
C9—C14—C13121.6 (4)C19—C18—C17118.4 (4)
C9—C14—H14119.2C19—C18—H18120.8
C17—C16—H16120.3C27—C28—H28120.3
C15—C16—C17119.3 (4)C27—C28—C29119.4 (4)
C15—C16—H16120.3C29—C28—H28120.3
C9—C8—H8117.5N1—C15—C16123.7 (4)
C7—C8—C9125.0 (4)N1—C15—H15118.1
C7—C8—H8117.5C16—C15—H15118.1
C31—C30—N7114.6 (4)C20—C21—H21121.1
C31—C30—C34119.2 (4)C22—C21—C20117.8 (4)
C34—C30—N7126.2 (4)C22—C21—H21121.1
O2—C11—C10117.0 (4)N4—C22—C21124.8 (4)
C12—C11—O2121.8 (4)N4—C22—H22117.6
C12—C11—C10121.2 (4)C21—C22—H22117.6
C5—C6—C1121.0 (4)N5—C29—C28123.2 (4)
C5—C6—H6119.5N5—C29—H29118.4
C1—C6—H6119.5C28—C29—H29118.4
C13—C12—H12120.2
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
O1—H1···N5i0.88 (2)1.80 (2)2.671 (5)169 (5)
O3—H3···N8ii0.85 (2)1.94 (2)2.789 (4)176 (4)
O2—H2···N1iii0.83 (2)1.95 (2)2.766 (5)166 (5)
Symmetry codes: (i) x+1, y, z+3/2; (ii) x+1, y, z+1; (iii) x+1/2, y+1/2, z+1.
 

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