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
CCDC references: 1881579; 1881580; 1881582; 1881583; 1881584; 1881585; 1960764
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).
Crystal data top
2(C14H12O3)·3(C12H12N2) | Z = 1 |
Mr = 1009.18 | F(000) = 534 |
Triclinic, P1 | Dx = 1.245 Mg m−3 |
a = 8.0448 (11) Å | Mo Kα radiation, λ = 0.71073 Å |
b = 9.9408 (14) Å | Cell parameters from 3481 reflections |
c = 17.371 (3) Å | θ = 2.4–27.4° |
α = 104.203 (2)° | µ = 0.08 mm−1 |
β = 90.628 (3)° | T = 220 K |
γ = 91.751 (4)° | Block, clear light colourless |
V = 1345.9 (3) Å3 | 0.19 × 0.15 × 0.11 mm |
Data collection top
Bruker APEX-II CCD diffractometer | 4129 reflections with I > 2σ(I) |
φ and ω scans | Rint = 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 = 0.746 | h = −10→10 |
12275 measured reflections | k = −10→12 |
6094 independent reflections | l = −22→22 |
Refinement top
Refinement on F2 | Primary atom site location: structure-invariant direct methods |
Least-squares matrix: full | Hydrogen site location: mixed |
R[F2 > 2σ(F2)] = 0.066 | H 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 reflections | Δρmax = 0.56 e Å−3 |
391 parameters | Δρmin = −0.39 e Å−3 |
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 | x | y | z | Uiso*/Ueq | Occ. (<1) |
O2 | 0.3190 (2) | 0.36328 (19) | 0.47493 (8) | 0.0481 (4) | |
O3 | 0.2216 (2) | 0.09946 (19) | 0.20639 (9) | 0.0516 (5) | |
O1 | 1.3895 (2) | 0.6223 (2) | 0.14182 (12) | 0.0583 (5) | |
N2 | 0.0612 (2) | 0.0010 (2) | 0.74080 (11) | 0.0461 (5) | |
N3 | 0.5060 (2) | 0.7790 (2) | 0.04721 (12) | 0.0493 (5) | |
C9 | 0.5457 (2) | 0.3543 (2) | 0.29385 (12) | 0.0328 (4) | |
C12 | 0.2616 (2) | 0.2308 (2) | 0.34152 (11) | 0.0332 (4) | |
H12 | 0.165851 | 0.188965 | 0.357378 | 0.040* | |
C10 | 0.4991 (2) | 0.3899 (2) | 0.37337 (11) | 0.0346 (4) | |
H10 | 0.563315 | 0.455514 | 0.411046 | 0.041* | |
C11 | 0.3567 (2) | 0.3276 (2) | 0.39661 (11) | 0.0340 (4) | |
C4 | 0.9165 (2) | 0.4758 (2) | 0.18421 (12) | 0.0359 (5) | |
C8 | 0.7010 (2) | 0.4177 (2) | 0.27279 (12) | 0.0355 (5) | |
H8 | 0.773170 | 0.460240 | 0.315322 | 0.043* | |
C13 | 0.3087 (2) | 0.1960 (2) | 0.26238 (11) | 0.0346 (5) | |
N1 | 1.0208 (3) | 0.2739 (3) | 0.51822 (13) | 0.0594 (6) | |
C7 | 0.7513 (3) | 0.4220 (2) | 0.20085 (13) | 0.0382 (5) | |
H7 | 0.676969 | 0.388642 | 0.157802 | 0.046* | |
C14 | 0.4499 (2) | 0.2575 (2) | 0.23860 (12) | 0.0352 (5) | |
H14 | 0.480600 | 0.233617 | 0.185029 | 0.042* | |
C1 | 1.2311 (3) | 0.5790 (2) | 0.15328 (14) | 0.0419 (5) | |
C6 | 1.0979 (3) | 0.5808 (2) | 0.10275 (13) | 0.0453 (6) | |
H6 | 1.112111 | 0.617319 | 0.058117 | 0.054* | |
C5 | 0.9427 (3) | 0.5284 (2) | 0.11801 (13) | 0.0439 (5) | |
H5 | 0.853332 | 0.528485 | 0.082699 | 0.053* | |
C3 | 1.0525 (3) | 0.4754 (2) | 0.23381 (14) | 0.0442 (5) | |
H3A | 1.038875 | 0.439389 | 0.278651 | 0.053* | |
C2 | 1.2080 (3) | 0.5266 (3) | 0.21927 (15) | 0.0468 (6) | |
H2A | 1.297701 | 0.525675 | 0.254227 | 0.056* | |
C29 | 0.7733 (3) | 0.9356 (3) | 0.00840 (14) | 0.0443 (5) | |
C27 | 0.6063 (3) | 0.7264 (3) | −0.01224 (14) | 0.0484 (6) | |
H27 | 0.585418 | 0.634366 | −0.041415 | 0.058* | |
C28 | 0.7391 (3) | 0.7995 (3) | −0.03337 (14) | 0.0488 (6) | |
H28 | 0.806285 | 0.757412 | −0.075891 | 0.059* | |
C22 | 0.3719 (3) | 0.0935 (3) | 0.70067 (14) | 0.0486 (6) | |
C24 | 0.1695 (3) | −0.0838 (3) | 0.70020 (17) | 0.0532 (6) | |
H24 | 0.140594 | −0.179133 | 0.685623 | 0.064* | |
C23 | 0.3220 (3) | −0.0421 (3) | 0.67775 (16) | 0.0509 (6) | |
H23 | 0.391443 | −0.107377 | 0.646563 | 0.061* | |
C31 | 0.5400 (3) | 0.9101 (3) | 0.08766 (15) | 0.0540 (6) | |
H31 | 0.471089 | 0.949858 | 0.129956 | 0.065* | |
C30 | 0.6707 (3) | 0.9896 (3) | 0.07046 (15) | 0.0521 (6) | |
H30 | 0.689970 | 1.080880 | 0.101121 | 0.062* | |
C32 | 0.9175 (3) | 1.0205 (3) | −0.01293 (17) | 0.0540 (6) | |
H32A | 0.916920 | 1.009074 | −0.070595 | 0.065* | |
H32B | 0.902230 | 1.118905 | 0.012011 | 0.065* | |
C18 | 0.7284 (3) | 0.2898 (3) | 0.53178 (18) | 0.0628 (7) | |
H18A | 0.635369 | 0.344566 | 0.531369 | 0.075* | 0.5 |
H18 | 0.630694 | 0.313691 | 0.508876 | 0.075* | 0.5 |
C21 | 0.5410 (4) | 0.1414 (3) | 0.67899 (18) | 0.0688 (9) | |
H21C | 0.627854 | 0.092360 | 0.699989 | 0.083* | 0.5 |
H21D | 0.558158 | 0.241093 | 0.702486 | 0.083* | 0.5 |
H21A | 0.587922 | 0.209557 | 0.725358 | 0.083* | 0.5 |
H21B | 0.613220 | 0.061479 | 0.668635 | 0.083* | 0.5 |
C25 | 0.1112 (4) | 0.1314 (3) | 0.7635 (2) | 0.0818 (11) | |
H25 | 0.038359 | 0.194835 | 0.793675 | 0.098* | |
C19 | 0.8799 (4) | 0.3262 (3) | 0.5064 (2) | 0.0702 (8) | |
H19 | 0.882004 | 0.395318 | 0.477933 | 0.084* | |
C26 | 0.2644 (4) | 0.1815 (3) | 0.7460 (2) | 0.0886 (13) | |
H26 | 0.294389 | 0.276101 | 0.765171 | 0.106* | |
C17A | 0.7166 (8) | 0.1613 (6) | 0.5597 (4) | 0.0439 (14) | 0.5 |
C20A | 0.5530 (6) | 0.1106 (7) | 0.5847 (3) | 0.0516 (12) | 0.5 |
H20A | 0.539264 | 0.010373 | 0.561858 | 0.062* | 0.5 |
H20B | 0.462482 | 0.156166 | 0.563995 | 0.062* | 0.5 |
C15A | 1.0026 (8) | 0.1367 (8) | 0.5340 (5) | 0.0749 (17) | 0.5 |
H15A | 1.094627 | 0.079195 | 0.527658 | 0.090* | 0.5 |
C16A | 0.8564 (8) | 0.0902 (8) | 0.5576 (4) | 0.0744 (17) | 0.5 |
H16A | 0.852771 | 0.005810 | 0.572911 | 0.089* | 0.5 |
C16B | 0.8688 (7) | 0.1920 (8) | 0.6123 (4) | 0.0701 (16) | 0.5 |
H16B | 0.870661 | 0.147333 | 0.654059 | 0.084* | 0.5 |
C15B | 1.0156 (6) | 0.2234 (7) | 0.5792 (4) | 0.0604 (14) | 0.5 |
H15B | 1.116430 | 0.206797 | 0.602512 | 0.072* | 0.5 |
C20B | 0.5481 (7) | 0.1972 (8) | 0.6173 (4) | 0.0647 (15) | 0.5 |
H20C | 0.491078 | 0.285340 | 0.631739 | 0.078* | 0.5 |
H20D | 0.482973 | 0.135973 | 0.573854 | 0.078* | 0.5 |
C17B | 0.7183 (7) | 0.2266 (7) | 0.5837 (4) | 0.0475 (14) | 0.5 |
H2 | 0.218 (4) | 0.330 (3) | 0.4846 (18) | 0.069 (9)* | |
H1 | 1.387 (5) | 0.668 (4) | 0.097 (2) | 0.105 (13)* | |
H3 | 0.128 (4) | 0.068 (3) | 0.2294 (16) | 0.062 (8)* | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
O2 | 0.0362 (8) | 0.0664 (11) | 0.0355 (8) | −0.0144 (8) | 0.0076 (6) | 0.0025 (7) |
O3 | 0.0444 (9) | 0.0616 (11) | 0.0394 (8) | −0.0282 (8) | 0.0081 (7) | −0.0019 (7) |
O1 | 0.0363 (9) | 0.0611 (12) | 0.0816 (12) | −0.0128 (8) | 0.0181 (8) | 0.0263 (10) |
N2 | 0.0364 (10) | 0.0441 (11) | 0.0538 (11) | −0.0123 (8) | 0.0094 (8) | 0.0059 (9) |
N3 | 0.0376 (10) | 0.0540 (13) | 0.0556 (11) | −0.0109 (9) | 0.0123 (9) | 0.0134 (9) |
C9 | 0.0245 (9) | 0.0303 (10) | 0.0436 (10) | −0.0024 (8) | 0.0055 (8) | 0.0093 (8) |
C12 | 0.0222 (9) | 0.0381 (11) | 0.0384 (10) | −0.0061 (8) | 0.0047 (7) | 0.0083 (8) |
C10 | 0.0270 (9) | 0.0356 (11) | 0.0381 (10) | −0.0067 (8) | 0.0014 (8) | 0.0041 (8) |
C11 | 0.0287 (9) | 0.0381 (11) | 0.0342 (9) | 0.0010 (8) | 0.0043 (7) | 0.0067 (8) |
C4 | 0.0311 (10) | 0.0311 (11) | 0.0447 (11) | −0.0048 (8) | 0.0095 (8) | 0.0081 (8) |
C8 | 0.0267 (9) | 0.0336 (11) | 0.0451 (11) | −0.0071 (8) | 0.0032 (8) | 0.0083 (8) |
C13 | 0.0281 (9) | 0.0349 (11) | 0.0383 (10) | −0.0074 (8) | 0.0033 (8) | 0.0050 (8) |
N1 | 0.0353 (10) | 0.0901 (18) | 0.0573 (12) | −0.0044 (11) | 0.0141 (9) | 0.0271 (12) |
C7 | 0.0295 (10) | 0.0379 (12) | 0.0466 (11) | −0.0070 (8) | 0.0051 (8) | 0.0099 (9) |
C14 | 0.0316 (10) | 0.0362 (11) | 0.0361 (9) | −0.0064 (8) | 0.0083 (8) | 0.0061 (8) |
C1 | 0.0322 (10) | 0.0333 (11) | 0.0593 (13) | −0.0044 (8) | 0.0162 (9) | 0.0094 (9) |
C6 | 0.0489 (13) | 0.0471 (14) | 0.0404 (11) | −0.0092 (10) | 0.0148 (10) | 0.0122 (10) |
C5 | 0.0404 (12) | 0.0492 (14) | 0.0412 (11) | −0.0079 (10) | 0.0044 (9) | 0.0103 (10) |
C3 | 0.0331 (11) | 0.0478 (14) | 0.0597 (13) | −0.0015 (9) | 0.0073 (10) | 0.0287 (11) |
C2 | 0.0298 (10) | 0.0476 (14) | 0.0692 (15) | −0.0037 (9) | 0.0038 (10) | 0.0263 (12) |
C29 | 0.0337 (11) | 0.0526 (14) | 0.0500 (12) | −0.0092 (10) | 0.0007 (9) | 0.0203 (10) |
C27 | 0.0438 (12) | 0.0454 (14) | 0.0519 (12) | −0.0132 (10) | 0.0081 (10) | 0.0058 (10) |
C28 | 0.0381 (12) | 0.0568 (15) | 0.0491 (12) | −0.0093 (10) | 0.0112 (10) | 0.0092 (11) |
C22 | 0.0416 (12) | 0.0469 (14) | 0.0529 (13) | −0.0128 (10) | 0.0143 (10) | 0.0050 (10) |
C24 | 0.0382 (12) | 0.0357 (13) | 0.0858 (18) | −0.0054 (10) | 0.0059 (12) | 0.0157 (12) |
C23 | 0.0344 (11) | 0.0458 (14) | 0.0730 (16) | 0.0034 (10) | 0.0099 (11) | 0.0153 (12) |
C31 | 0.0459 (13) | 0.0582 (16) | 0.0551 (13) | −0.0069 (11) | 0.0174 (11) | 0.0091 (12) |
C30 | 0.0467 (13) | 0.0454 (14) | 0.0604 (14) | −0.0110 (11) | 0.0045 (11) | 0.0073 (11) |
C32 | 0.0386 (12) | 0.0613 (16) | 0.0674 (15) | −0.0148 (11) | 0.0030 (11) | 0.0279 (13) |
C18 | 0.0362 (13) | 0.080 (2) | 0.0785 (18) | 0.0066 (13) | 0.0122 (12) | 0.0309 (16) |
C21 | 0.0502 (15) | 0.074 (2) | 0.0731 (17) | −0.0249 (14) | 0.0226 (13) | 0.0035 (15) |
C25 | 0.0632 (18) | 0.0464 (16) | 0.120 (3) | −0.0097 (13) | 0.0528 (19) | −0.0113 (16) |
C19 | 0.0501 (16) | 0.073 (2) | 0.099 (2) | 0.0003 (14) | 0.0215 (15) | 0.0423 (17) |
C26 | 0.075 (2) | 0.0414 (16) | 0.132 (3) | −0.0201 (14) | 0.054 (2) | −0.0120 (17) |
C17A | 0.045 (3) | 0.040 (3) | 0.048 (3) | −0.002 (2) | 0.015 (2) | 0.014 (2) |
C20A | 0.042 (2) | 0.058 (3) | 0.054 (2) | −0.013 (2) | 0.011 (2) | 0.014 (2) |
C15A | 0.058 (3) | 0.081 (4) | 0.096 (4) | 0.014 (3) | 0.024 (3) | 0.038 (3) |
C16A | 0.066 (3) | 0.075 (3) | 0.099 (4) | 0.012 (3) | 0.023 (3) | 0.050 (3) |
C16B | 0.052 (3) | 0.103 (4) | 0.072 (3) | −0.002 (3) | 0.007 (2) | 0.054 (3) |
C15B | 0.035 (2) | 0.090 (4) | 0.066 (3) | 0.003 (2) | 0.002 (2) | 0.038 (3) |
C20B | 0.047 (3) | 0.080 (4) | 0.076 (3) | 0.003 (3) | 0.008 (2) | 0.037 (3) |
C17B | 0.032 (2) | 0.062 (4) | 0.054 (3) | 0.004 (3) | 0.011 (2) | 0.024 (3) |
Geometric parameters (Å, º) top
O2—C11 | 1.359 (2) | C28—H28 | 0.9400 |
O2—H2 | 0.90 (3) | C22—C23 | 1.355 (3) |
O3—C13 | 1.358 (2) | C22—C21 | 1.510 (3) |
O3—H3 | 0.93 (3) | C22—C26 | 1.363 (4) |
O1—C1 | 1.365 (2) | C24—H24 | 0.9400 |
O1—H1 | 0.98 (4) | C24—C23 | 1.374 (3) |
N2—C24 | 1.317 (3) | C23—H23 | 0.9400 |
N2—C25 | 1.308 (3) | C31—H31 | 0.9400 |
N3—C27 | 1.330 (3) | C31—C30 | 1.375 (3) |
N3—C31 | 1.339 (3) | C30—H30 | 0.9400 |
C9—C10 | 1.398 (3) | C32—C32i | 1.497 (5) |
C9—C8 | 1.472 (3) | C32—H32A | 0.9800 |
C9—C14 | 1.388 (3) | C32—H32B | 0.9800 |
C12—H12 | 0.9400 | C18—H18A | 0.9400 |
C12—C11 | 1.383 (3) | C18—H18 | 0.9400 |
C12—C13 | 1.393 (3) | C18—C19 | 1.369 (4) |
C10—H10 | 0.9400 | C18—C17A | 1.474 (7) |
C10—C11 | 1.396 (3) | C18—C17B | 1.221 (7) |
C4—C7 | 1.475 (3) | C21—H21C | 0.9800 |
C4—C5 | 1.390 (3) | C21—H21D | 0.9800 |
C4—C3 | 1.386 (3) | C21—H21A | 0.9800 |
C8—H8 | 0.9400 | C21—H21B | 0.9800 |
C8—C7 | 1.328 (3) | C21—C20A | 1.595 (6) |
C13—C14 | 1.388 (3) | C21—C20B | 1.324 (7) |
N1—C19 | 1.296 (4) | C25—H25 | 0.9400 |
N1—C15A | 1.459 (8) | C25—C26 | 1.380 (4) |
N1—C15B | 1.279 (6) | C19—H19 | 0.9400 |
C7—H7 | 0.9400 | C26—H26 | 0.9400 |
C14—H14 | 0.9400 | C17A—C20A | 1.502 (8) |
C1—C6 | 1.380 (4) | C17A—C16A | 1.343 (9) |
C1—C2 | 1.383 (3) | C20A—H20A | 0.9800 |
C6—H6 | 0.9400 | C20A—H20B | 0.9800 |
C6—C5 | 1.392 (3) | C15A—H15A | 0.9400 |
C5—H5 | 0.9400 | C15A—C16A | 1.355 (9) |
C3—H3A | 0.9400 | C16A—H16A | 0.9400 |
C3—C2 | 1.384 (3) | C16B—H16B | 0.9400 |
C2—H2A | 0.9400 | C16B—C15B | 1.379 (7) |
C29—C28 | 1.387 (3) | C16B—C17B | 1.387 (9) |
C29—C30 | 1.376 (3) | C15B—H15B | 0.9400 |
C29—C32 | 1.516 (3) | C20B—H20C | 0.9800 |
C27—H27 | 0.9400 | C20B—H20D | 0.9800 |
C27—C28 | 1.377 (3) | C20B—C17B | 1.542 (8) |
| | | |
C11—O2—H2 | 112.6 (19) | N3—C31—C30 | 123.3 (2) |
C13—O3—H3 | 109.4 (17) | C30—C31—H31 | 118.3 |
C1—O1—H1 | 108 (2) | C29—C30—H30 | 120.0 |
C25—N2—C24 | 115.4 (2) | C31—C30—C29 | 120.1 (2) |
C27—N3—C31 | 116.57 (19) | C31—C30—H30 | 120.0 |
C10—C9—C8 | 117.80 (17) | C29—C32—H32A | 109.0 |
C14—C9—C10 | 119.73 (17) | C29—C32—H32B | 109.0 |
C14—C9—C8 | 122.41 (17) | C32i—C32—C29 | 112.8 (3) |
C11—C12—H12 | 120.3 | C32i—C32—H32A | 109.0 |
C11—C12—C13 | 119.50 (17) | C32i—C32—H32B | 109.0 |
C13—C12—H12 | 120.3 | H32A—C32—H32B | 107.8 |
C9—C10—H10 | 120.1 | C19—C18—H18A | 121.3 |
C11—C10—C9 | 119.74 (17) | C19—C18—H18 | 119.5 |
C11—C10—H10 | 120.1 | C19—C18—C17A | 117.5 (3) |
O2—C11—C12 | 122.09 (17) | C17A—C18—H18A | 121.3 |
O2—C11—C10 | 117.43 (18) | C17B—C18—H18 | 119.5 |
C12—C11—C10 | 120.46 (17) | C17B—C18—C19 | 120.9 (4) |
C5—C4—C7 | 121.5 (2) | C22—C21—H21C | 109.8 |
C3—C4—C7 | 121.32 (19) | C22—C21—H21D | 109.8 |
C3—C4—C5 | 117.14 (18) | C22—C21—H21A | 108.0 |
C9—C8—H8 | 116.1 | C22—C21—H21B | 108.0 |
C7—C8—C9 | 127.72 (19) | C22—C21—C20A | 109.4 (3) |
C7—C8—H8 | 116.1 | H21C—C21—H21D | 108.2 |
O3—C13—C12 | 121.73 (17) | H21A—C21—H21B | 107.2 |
O3—C13—C14 | 117.74 (17) | C20A—C21—H21C | 109.8 |
C14—C13—C12 | 120.52 (17) | C20A—C21—H21D | 109.8 |
C19—N1—C15A | 113.2 (3) | C20B—C21—C22 | 117.2 (4) |
C15B—N1—C19 | 111.0 (3) | C20B—C21—H21A | 108.0 |
C4—C7—H7 | 117.9 | C20B—C21—H21B | 108.0 |
C8—C7—C4 | 124.2 (2) | N2—C25—H25 | 118.0 |
C8—C7—H7 | 117.9 | N2—C25—C26 | 124.1 (2) |
C9—C14—H14 | 120.0 | C26—C25—H25 | 118.0 |
C13—C14—C9 | 120.06 (17) | N1—C19—C18 | 125.8 (3) |
C13—C14—H14 | 120.0 | N1—C19—H19 | 117.1 |
O1—C1—C6 | 124.5 (2) | C18—C19—H19 | 117.1 |
O1—C1—C2 | 116.1 (2) | C22—C26—C25 | 119.7 (3) |
C6—C1—C2 | 119.45 (19) | C22—C26—H26 | 120.1 |
C1—C6—H6 | 120.1 | C25—C26—H26 | 120.1 |
C1—C6—C5 | 119.9 (2) | C18—C17A—C20A | 120.7 (5) |
C5—C6—H6 | 120.1 | C16A—C17A—C18 | 116.6 (5) |
C4—C5—C6 | 121.6 (2) | C16A—C17A—C20A | 122.6 (6) |
C4—C5—H5 | 119.2 | C21—C20A—H20A | 109.3 |
C6—C5—H5 | 119.2 | C21—C20A—H20B | 109.3 |
C4—C3—H3A | 119.0 | C17A—C20A—C21 | 111.8 (4) |
C2—C3—C4 | 122.0 (2) | C17A—C20A—H20A | 109.3 |
C2—C3—H3A | 119.0 | C17A—C20A—H20B | 109.3 |
C1—C2—C3 | 119.9 (2) | H20A—C20A—H20B | 107.9 |
C1—C2—H2A | 120.0 | N1—C15A—H15A | 119.2 |
C3—C2—H2A | 120.0 | C16A—C15A—N1 | 121.6 (5) |
C28—C29—C32 | 121.6 (2) | C16A—C15A—H15A | 119.2 |
C30—C29—C28 | 116.8 (2) | C17A—C16A—C15A | 121.8 (6) |
C30—C29—C32 | 121.6 (2) | C17A—C16A—H16A | 119.1 |
N3—C27—H27 | 118.2 | C15A—C16A—H16A | 119.1 |
N3—C27—C28 | 123.6 (2) | C15B—C16B—H16B | 120.1 |
C28—C27—H27 | 118.2 | C15B—C16B—C17B | 119.9 (5) |
C29—C28—H28 | 120.2 | C17B—C16B—H16B | 120.1 |
C27—C28—C29 | 119.7 (2) | N1—C15B—C16B | 123.0 (5) |
C27—C28—H28 | 120.2 | N1—C15B—H15B | 118.5 |
C23—C22—C21 | 120.9 (2) | C16B—C15B—H15B | 118.5 |
C23—C22—C26 | 116.5 (2) | C21—C20B—H20C | 107.4 |
C26—C22—C21 | 122.5 (2) | C21—C20B—H20D | 107.4 |
N2—C24—H24 | 117.9 | C21—C20B—C17B | 119.8 (5) |
N2—C24—C23 | 124.3 (2) | H20C—C20B—H20D | 106.9 |
C23—C24—H24 | 117.9 | C17B—C20B—H20C | 107.4 |
C22—C23—C24 | 119.8 (2) | C17B—C20B—H20D | 107.4 |
C22—C23—H23 | 120.1 | C18—C17B—C16B | 115.5 (5) |
C24—C23—H23 | 120.1 | C18—C17B—C20B | 120.7 (5) |
N3—C31—H31 | 118.3 | C16B—C17B—C20B | 123.7 (5) |
Symmetry code: (i) −x+2, −y+2, −z. |
Crystal data top
C14H12O3·2(C12H10N2) | F(000) = 1248 |
Mr = 592.67 | Dx = 1.262 Mg m−3 |
Monoclinic, P21/c | Mo Kα radiation, λ = 0.71073 Å |
a = 8.9669 (16) Å | Cell parameters from 1985 reflections |
b = 36.365 (6) Å | θ = 2.2–19.2° |
c = 9.6042 (19) Å | µ = 0.08 mm−1 |
β = 94.898 (6)° | T = 230 K |
V = 3120.3 (10) Å3 | Block, clear yellowish colourless |
Z = 4 | 0.2 × 0.11 × 0.08 mm |
Data collection top
Bruker APEX-II CCD diffractometer | 3368 reflections with I > 2σ(I) |
φ and ω scans | Rint = 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 = 0.746 | h = −10→11 |
28472 measured reflections | k = −47→47 |
7190 independent reflections | l = −12→12 |
Refinement top
Refinement on F2 | Primary atom site location: dual |
Least-squares matrix: full | Hydrogen site location: mixed |
R[F2 > 2σ(F2)] = 0.058 | H 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 reflections | Δρmax = 0.37 e Å−3 |
418 parameters | Δρmin = −0.21 e Å−3 |
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 | x | y | z | Uiso*/Ueq | |
O1 | 1.4411 (2) | 0.27475 (5) | 1.0440 (2) | 0.0554 (5) | |
O2 | 0.4016 (2) | 0.42892 (5) | 0.73444 (19) | 0.0555 (5) | |
O3 | 0.7522 (2) | 0.52049 (5) | 0.9082 (2) | 0.0592 (5) | |
N3 | 0.2388 (2) | 0.48893 (5) | 0.6494 (2) | 0.0513 (6) | |
N4 | −0.3079 (2) | 0.70687 (5) | 0.4803 (2) | 0.0510 (6) | |
N1 | 0.5345 (3) | 0.56683 (5) | 0.7748 (2) | 0.0551 (6) | |
C1 | 1.3391 (3) | 0.30158 (6) | 1.0144 (2) | 0.0418 (6) | |
C2 | 1.1869 (3) | 0.29513 (6) | 0.9879 (2) | 0.0435 (6) | |
H2A | 1.150339 | 0.270905 | 0.987701 | 0.052* | |
C3 | 1.0892 (3) | 0.32391 (7) | 0.9621 (2) | 0.0460 (6) | |
H3A | 0.986298 | 0.318989 | 0.945058 | 0.055* | |
C4 | 1.1390 (3) | 0.36034 (6) | 0.9604 (2) | 0.0475 (6) | |
C11 | 0.5385 (3) | 0.43941 (6) | 0.7903 (2) | 0.0439 (6) | |
C12 | 0.5726 (3) | 0.47587 (6) | 0.8224 (2) | 0.0439 (6) | |
H12 | 0.499216 | 0.494238 | 0.807083 | 0.053* | |
C13 | 0.7156 (3) | 0.48484 (6) | 0.8772 (2) | 0.0450 (6) | |
C29 | 0.0756 (3) | 0.55191 (6) | 0.5692 (3) | 0.0465 (6) | |
C34 | −0.1532 (3) | 0.64191 (7) | 0.5555 (3) | 0.0487 (6) | |
C17 | 0.3781 (3) | 0.62228 (7) | 0.6203 (3) | 0.0486 (7) | |
C9 | 0.7890 (3) | 0.42123 (7) | 0.8724 (2) | 0.0483 (6) | |
C22 | 0.2645 (3) | 0.69724 (7) | 0.3449 (3) | 0.0512 (7) | |
C14 | 0.8241 (3) | 0.45771 (7) | 0.9042 (2) | 0.0464 (6) | |
H14 | 0.920261 | 0.464016 | 0.943532 | 0.056* | |
C10 | 0.6467 (3) | 0.41249 (7) | 0.8161 (2) | 0.0489 (7) | |
H10 | 0.622757 | 0.387844 | 0.794951 | 0.059* | |
C33 | −0.0732 (3) | 0.60791 (7) | 0.6012 (3) | 0.0530 (7) | |
H33 | −0.070890 | 0.601960 | 0.696612 | 0.064* | |
C7 | 1.0373 (3) | 0.39199 (7) | 0.9353 (3) | 0.0528 (7) | |
H7 | 1.079354 | 0.415550 | 0.948150 | 0.063* | |
C36 | −0.2593 (3) | 0.68409 (7) | 0.3851 (3) | 0.0559 (7) | |
H36 | −0.277904 | 0.690466 | 0.290375 | 0.067* | |
C8 | 0.8961 (3) | 0.39030 (7) | 0.8972 (3) | 0.0553 (7) | |
H8 | 0.856012 | 0.366568 | 0.883528 | 0.066* | |
C20 | 0.2975 (3) | 0.65228 (7) | 0.5433 (3) | 0.0532 (7) | |
H20 | 0.211233 | 0.661549 | 0.580197 | 0.064* | |
C6 | 1.3891 (3) | 0.33760 (7) | 1.0098 (3) | 0.0510 (7) | |
H6 | 1.492179 | 0.342516 | 1.024737 | 0.061* | |
C21 | 0.3369 (3) | 0.66723 (7) | 0.4262 (3) | 0.0541 (7) | |
H21 | 0.422693 | 0.657243 | 0.390822 | 0.065* | |
N2 | 0.1407 (3) | 0.75643 (8) | 0.1870 (3) | 0.0861 (8) | |
C18 | 0.3361 (3) | 0.61091 (7) | 0.7484 (3) | 0.0546 (7) | |
H18 | 0.253971 | 0.621967 | 0.786471 | 0.066* | |
C5 | 1.2914 (3) | 0.36601 (7) | 0.9839 (3) | 0.0529 (7) | |
H5 | 1.328875 | 0.390132 | 0.981966 | 0.063* | |
C32 | −0.0056 (3) | 0.58537 (7) | 0.5218 (3) | 0.0525 (6) | |
H32 | −0.008968 | 0.591006 | 0.426053 | 0.063* | |
C30 | 0.0563 (3) | 0.53388 (7) | 0.6933 (3) | 0.0567 (7) | |
H30 | −0.013459 | 0.542659 | 0.753007 | 0.068* | |
C35 | −0.1837 (3) | 0.65193 (7) | 0.4168 (3) | 0.0563 (7) | |
H35 | −0.152816 | 0.636862 | 0.345068 | 0.068* | |
C31 | 0.1398 (3) | 0.50306 (7) | 0.7287 (3) | 0.0562 (7) | |
H31 | 0.125730 | 0.491398 | 0.813895 | 0.067* | |
C28 | 0.1785 (3) | 0.53715 (7) | 0.4869 (3) | 0.0570 (7) | |
H28 | 0.195057 | 0.548105 | 0.400916 | 0.068* | |
C27 | 0.2566 (3) | 0.50643 (7) | 0.5310 (3) | 0.0598 (8) | |
H27 | 0.327513 | 0.497115 | 0.473552 | 0.072* | |
C16 | 0.4959 (3) | 0.60405 (7) | 0.5712 (3) | 0.0590 (8) | |
H16 | 0.526330 | 0.609943 | 0.482659 | 0.071* | |
C37 | −0.2793 (4) | 0.69645 (7) | 0.6126 (3) | 0.0629 (8) | |
H37 | −0.313758 | 0.711550 | 0.682548 | 0.075* | |
C38 | −0.2033 (3) | 0.66536 (7) | 0.6533 (3) | 0.0607 (8) | |
H38 | −0.184981 | 0.659904 | 0.748934 | 0.073* | |
C15 | 0.5696 (3) | 0.57750 (7) | 0.6491 (3) | 0.0616 (8) | |
H15 | 0.650825 | 0.565866 | 0.611651 | 0.074* | |
C26 | 0.1311 (3) | 0.71328 (8) | 0.3724 (3) | 0.0612 (8) | |
H26 | 0.078522 | 0.704474 | 0.446136 | 0.073* | |
C19 | 0.4150 (3) | 0.58325 (8) | 0.8204 (3) | 0.0580 (7) | |
H19 | 0.382717 | 0.575591 | 0.906386 | 0.070* | |
C23 | 0.3326 (3) | 0.71179 (8) | 0.2329 (3) | 0.0669 (8) | |
H23 | 0.422802 | 0.701656 | 0.207296 | 0.080* | |
C25 | 0.0753 (4) | 0.74196 (9) | 0.2925 (3) | 0.0742 (9) | |
H25 | −0.016291 | 0.752167 | 0.314009 | 0.089* | |
C24 | 0.2694 (4) | 0.74059 (10) | 0.1601 (4) | 0.0883 (11) | |
H24 | 0.319574 | 0.750023 | 0.085792 | 0.106* | |
H2 | 0.344 (3) | 0.4479 (6) | 0.706 (3) | 0.079 (10)* | |
H1 | 1.401 (3) | 0.2534 (5) | 1.040 (3) | 0.065 (9)* | |
H3 | 0.685 (3) | 0.5359 (7) | 0.882 (3) | 0.073 (10)* | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
O1 | 0.0430 (11) | 0.0442 (11) | 0.0782 (14) | 0.0036 (9) | −0.0007 (10) | 0.0023 (10) |
O2 | 0.0560 (13) | 0.0448 (11) | 0.0638 (12) | 0.0004 (10) | −0.0051 (10) | 0.0037 (9) |
O3 | 0.0554 (13) | 0.0529 (13) | 0.0679 (13) | −0.0035 (10) | −0.0033 (11) | 0.0025 (10) |
N3 | 0.0459 (14) | 0.0488 (13) | 0.0575 (14) | −0.0033 (10) | −0.0058 (12) | 0.0043 (10) |
N4 | 0.0524 (14) | 0.0476 (13) | 0.0518 (14) | −0.0036 (10) | −0.0020 (12) | 0.0016 (10) |
N1 | 0.0591 (15) | 0.0477 (13) | 0.0580 (15) | −0.0114 (11) | 0.0017 (13) | −0.0005 (10) |
C1 | 0.0455 (16) | 0.0431 (14) | 0.0371 (14) | 0.0021 (12) | 0.0052 (12) | 0.0007 (10) |
C2 | 0.0460 (16) | 0.0402 (14) | 0.0449 (14) | −0.0024 (12) | 0.0069 (13) | 0.0001 (11) |
C3 | 0.0410 (16) | 0.0567 (16) | 0.0397 (14) | −0.0001 (13) | −0.0004 (12) | −0.0001 (11) |
C4 | 0.0635 (19) | 0.0468 (14) | 0.0327 (13) | 0.0028 (11) | 0.0066 (13) | 0.0055 (10) |
C11 | 0.0505 (17) | 0.0434 (15) | 0.0380 (14) | 0.0024 (13) | 0.0052 (13) | 0.0048 (11) |
C12 | 0.0448 (16) | 0.0456 (15) | 0.0412 (14) | 0.0039 (12) | 0.0025 (13) | 0.0055 (11) |
C13 | 0.0544 (18) | 0.0446 (15) | 0.0369 (14) | −0.0043 (13) | 0.0088 (13) | 0.0023 (11) |
C29 | 0.0413 (15) | 0.0502 (13) | 0.0464 (15) | −0.0105 (10) | −0.0045 (13) | 0.0021 (11) |
C34 | 0.0493 (17) | 0.0508 (14) | 0.0457 (15) | −0.0057 (10) | 0.0022 (13) | 0.0026 (11) |
C17 | 0.0479 (17) | 0.0505 (15) | 0.0468 (15) | −0.0142 (13) | 0.0009 (14) | −0.0062 (12) |
C9 | 0.0556 (17) | 0.0562 (11) | 0.0342 (13) | 0.0047 (10) | 0.0104 (13) | 0.0036 (11) |
C22 | 0.0501 (18) | 0.0573 (16) | 0.0453 (15) | −0.0080 (13) | −0.0004 (14) | −0.0046 (12) |
C14 | 0.0414 (15) | 0.0608 (12) | 0.0368 (14) | −0.0021 (12) | 0.0027 (12) | 0.0028 (11) |
C10 | 0.0603 (19) | 0.0452 (15) | 0.0410 (15) | 0.0076 (13) | 0.0031 (13) | −0.0003 (11) |
C33 | 0.0549 (18) | 0.0573 (14) | 0.0461 (15) | 0.0004 (12) | 0.0009 (14) | 0.0041 (12) |
C7 | 0.061 (2) | 0.0555 (15) | 0.0418 (15) | 0.0068 (11) | 0.0018 (14) | 0.0044 (12) |
C36 | 0.0582 (19) | 0.0704 (19) | 0.0392 (15) | 0.0011 (15) | 0.0049 (14) | 0.0055 (13) |
C8 | 0.0580 (19) | 0.0601 (16) | 0.0473 (16) | 0.0074 (11) | 0.0027 (15) | 0.0019 (12) |
C20 | 0.0503 (18) | 0.0622 (17) | 0.0477 (16) | −0.0106 (14) | 0.0083 (14) | −0.0030 (13) |
C6 | 0.0451 (17) | 0.0485 (16) | 0.0596 (17) | −0.0054 (13) | 0.0048 (14) | −0.0017 (12) |
C21 | 0.0562 (18) | 0.0548 (16) | 0.0518 (16) | −0.0111 (13) | 0.0081 (15) | −0.0062 (13) |
N2 | 0.077 (2) | 0.111 (2) | 0.0720 (19) | 0.0308 (17) | 0.0159 (16) | 0.0251 (16) |
C18 | 0.0525 (18) | 0.0696 (18) | 0.0425 (15) | −0.0055 (14) | 0.0080 (14) | −0.0037 (13) |
C5 | 0.061 (2) | 0.0449 (15) | 0.0527 (16) | −0.0042 (14) | 0.0067 (15) | 0.0018 (12) |
C32 | 0.0543 (17) | 0.0540 (14) | 0.0489 (15) | −0.0016 (11) | 0.0021 (14) | 0.0027 (12) |
C30 | 0.0490 (17) | 0.0601 (17) | 0.0629 (19) | 0.0012 (14) | 0.0163 (15) | 0.0053 (14) |
C35 | 0.0606 (19) | 0.0652 (18) | 0.0440 (16) | 0.0116 (15) | 0.0096 (14) | −0.0016 (13) |
C31 | 0.0521 (18) | 0.0627 (18) | 0.0539 (17) | −0.0053 (15) | 0.0049 (15) | 0.0142 (14) |
C28 | 0.072 (2) | 0.0551 (17) | 0.0445 (15) | 0.0008 (15) | 0.0092 (15) | 0.0024 (12) |
C27 | 0.067 (2) | 0.0581 (18) | 0.0555 (17) | 0.0050 (15) | 0.0136 (16) | −0.0010 (14) |
C16 | 0.070 (2) | 0.0585 (18) | 0.0514 (16) | −0.0058 (15) | 0.0195 (16) | 0.0032 (13) |
C37 | 0.095 (2) | 0.0476 (16) | 0.0455 (17) | 0.0050 (15) | 0.0041 (17) | −0.0068 (12) |
C38 | 0.091 (2) | 0.0543 (17) | 0.0359 (15) | 0.0083 (15) | −0.0013 (15) | 0.0017 (12) |
C15 | 0.069 (2) | 0.0522 (17) | 0.0665 (19) | −0.0054 (15) | 0.0208 (17) | −0.0012 (14) |
C26 | 0.0548 (19) | 0.083 (2) | 0.0467 (16) | 0.0002 (16) | 0.0077 (15) | −0.0018 (15) |
C19 | 0.0600 (19) | 0.0696 (19) | 0.0449 (16) | −0.0131 (16) | 0.0080 (15) | 0.0047 (14) |
C23 | 0.0511 (19) | 0.091 (2) | 0.0595 (18) | 0.0077 (16) | 0.0134 (15) | 0.0167 (16) |
C25 | 0.064 (2) | 0.107 (3) | 0.0515 (18) | 0.0225 (19) | 0.0071 (17) | −0.0006 (17) |
C24 | 0.068 (2) | 0.119 (3) | 0.080 (2) | 0.022 (2) | 0.0218 (19) | 0.047 (2) |
Geometric parameters (Å, º) top
O1—C1 | 1.351 (3) | C14—H14 | 0.9400 |
O1—H1 | 0.855 (16) | C10—H10 | 0.9400 |
O2—C11 | 1.352 (3) | C33—H33 | 0.9400 |
O2—H2 | 0.893 (17) | C33—C32 | 1.304 (3) |
O3—C13 | 1.364 (3) | C7—H7 | 0.9400 |
O3—H3 | 0.845 (17) | C7—C8 | 1.289 (4) |
N3—C31 | 1.322 (3) | C36—H36 | 0.9400 |
N3—C27 | 1.325 (3) | C36—C35 | 1.373 (3) |
N4—C36 | 1.334 (3) | C8—H8 | 0.9400 |
N4—C37 | 1.330 (3) | C20—H20 | 0.9400 |
N1—C15 | 1.332 (3) | C20—C21 | 1.324 (3) |
N1—C19 | 1.333 (3) | C6—H6 | 0.9400 |
C1—C2 | 1.386 (3) | C6—C5 | 1.364 (3) |
C1—C6 | 1.386 (3) | C21—H21 | 0.9400 |
C2—H2A | 0.9400 | N2—C25 | 1.322 (4) |
C2—C3 | 1.374 (3) | N2—C24 | 1.335 (4) |
C3—H3A | 0.9400 | C18—H18 | 0.9400 |
C3—C4 | 1.399 (3) | C18—C19 | 1.381 (4) |
C4—C7 | 1.475 (4) | C5—H5 | 0.9400 |
C4—C5 | 1.382 (4) | C32—H32 | 0.9400 |
C11—C12 | 1.389 (3) | C30—H30 | 0.9400 |
C11—C10 | 1.386 (3) | C30—C31 | 1.374 (4) |
C12—H12 | 0.9400 | C35—H35 | 0.9400 |
C12—C13 | 1.383 (3) | C31—H31 | 0.9400 |
C13—C14 | 1.394 (3) | C28—H28 | 0.9400 |
C29—C32 | 1.470 (3) | C28—C27 | 1.366 (4) |
C29—C30 | 1.384 (3) | C27—H27 | 0.9400 |
C29—C28 | 1.374 (4) | C16—H16 | 0.9400 |
C34—C33 | 1.477 (3) | C16—C15 | 1.358 (4) |
C34—C35 | 1.385 (3) | C37—H37 | 0.9400 |
C34—C38 | 1.373 (3) | C37—C38 | 1.360 (4) |
C17—C20 | 1.473 (4) | C38—H38 | 0.9400 |
C17—C18 | 1.380 (3) | C15—H15 | 0.9400 |
C17—C16 | 1.364 (4) | C26—H26 | 0.9400 |
C9—C14 | 1.391 (3) | C26—C25 | 1.364 (4) |
C9—C10 | 1.379 (4) | C19—H19 | 0.9400 |
C9—C8 | 1.485 (4) | C23—H23 | 0.9400 |
C22—C21 | 1.462 (4) | C23—C24 | 1.356 (4) |
C22—C26 | 1.376 (4) | C25—H25 | 0.9400 |
C22—C23 | 1.387 (4) | C24—H24 | 0.9400 |
| | | |
C1—O1—H1 | 111.9 (19) | C21—C20—C17 | 125.1 (3) |
C11—O2—H2 | 112.9 (18) | C21—C20—H20 | 117.4 |
C13—O3—H3 | 114 (2) | C1—C6—H6 | 119.4 |
C31—N3—C27 | 116.3 (2) | C5—C6—C1 | 121.1 (3) |
C37—N4—C36 | 115.4 (2) | C5—C6—H6 | 119.4 |
C15—N1—C19 | 115.3 (2) | C22—C21—H21 | 115.8 |
O1—C1—C2 | 123.7 (2) | C20—C21—C22 | 128.4 (3) |
O1—C1—C6 | 118.3 (2) | C20—C21—H21 | 115.8 |
C6—C1—C2 | 118.1 (2) | C25—N2—C24 | 115.1 (3) |
C1—C2—H2A | 119.8 | C17—C18—H18 | 120.1 |
C3—C2—C1 | 120.5 (2) | C17—C18—C19 | 119.8 (3) |
C3—C2—H2A | 119.8 | C19—C18—H18 | 120.1 |
C2—C3—H3A | 119.2 | C4—C5—H5 | 119.1 |
C2—C3—C4 | 121.6 (2) | C6—C5—C4 | 121.9 (2) |
C4—C3—H3A | 119.2 | C6—C5—H5 | 119.1 |
C3—C4—C7 | 123.2 (3) | C29—C32—H32 | 117.2 |
C5—C4—C3 | 116.9 (2) | C33—C32—C29 | 125.6 (3) |
C5—C4—C7 | 120.0 (2) | C33—C32—H32 | 117.2 |
O2—C11—C12 | 122.1 (2) | C29—C30—H30 | 120.2 |
O2—C11—C10 | 118.0 (2) | C31—C30—C29 | 119.6 (3) |
C10—C11—C12 | 119.8 (2) | C31—C30—H30 | 120.2 |
C11—C12—H12 | 120.4 | C34—C35—H35 | 120.3 |
C13—C12—C11 | 119.2 (2) | C36—C35—C34 | 119.3 (2) |
C13—C12—H12 | 120.4 | C36—C35—H35 | 120.3 |
O3—C13—C12 | 120.4 (2) | N3—C31—C30 | 123.6 (2) |
O3—C13—C14 | 118.8 (2) | N3—C31—H31 | 118.2 |
C12—C13—C14 | 120.9 (2) | C30—C31—H31 | 118.2 |
C30—C29—C32 | 124.3 (3) | C29—C28—H28 | 120.2 |
C28—C29—C32 | 119.0 (2) | C27—C28—C29 | 119.5 (2) |
C28—C29—C30 | 116.7 (2) | C27—C28—H28 | 120.2 |
C35—C34—C33 | 123.8 (2) | N3—C27—C28 | 124.3 (3) |
C38—C34—C33 | 119.7 (2) | N3—C27—H27 | 117.9 |
C38—C34—C35 | 116.5 (2) | C28—C27—H27 | 117.9 |
C18—C17—C20 | 120.6 (3) | C17—C16—H16 | 119.7 |
C16—C17—C20 | 123.2 (2) | C15—C16—C17 | 120.7 (3) |
C16—C17—C18 | 116.1 (3) | C15—C16—H16 | 119.7 |
C14—C9—C8 | 123.8 (3) | N4—C37—H37 | 117.9 |
C10—C9—C14 | 119.3 (2) | N4—C37—C38 | 124.2 (2) |
C10—C9—C8 | 116.9 (2) | C38—C37—H37 | 117.9 |
C26—C22—C21 | 124.6 (3) | C34—C38—H38 | 119.8 |
C26—C22—C23 | 115.8 (3) | C37—C38—C34 | 120.3 (2) |
C23—C22—C21 | 119.6 (3) | C37—C38—H38 | 119.8 |
C13—C14—H14 | 120.2 | N1—C15—C16 | 124.4 (3) |
C9—C14—C13 | 119.5 (2) | N1—C15—H15 | 117.8 |
C9—C14—H14 | 120.2 | C16—C15—H15 | 117.8 |
C11—C10—H10 | 119.4 | C22—C26—H26 | 120.0 |
C9—C10—C11 | 121.2 (2) | C25—C26—C22 | 119.9 (3) |
C9—C10—H10 | 119.4 | C25—C26—H26 | 120.0 |
C34—C33—H33 | 116.9 | N1—C19—C18 | 123.6 (2) |
C32—C33—C34 | 126.2 (3) | N1—C19—H19 | 118.2 |
C32—C33—H33 | 116.9 | C18—C19—H19 | 118.2 |
C4—C7—H7 | 117.0 | C22—C23—H23 | 119.9 |
C8—C7—C4 | 126.0 (3) | C24—C23—C22 | 120.1 (3) |
C8—C7—H7 | 117.0 | C24—C23—H23 | 119.9 |
N4—C36—H36 | 117.9 | N2—C25—C26 | 124.7 (3) |
N4—C36—C35 | 124.2 (2) | N2—C25—H25 | 117.6 |
C35—C36—H36 | 117.9 | C26—C25—H25 | 117.6 |
C9—C8—H8 | 116.0 | N2—C24—C23 | 124.3 (3) |
C7—C8—C9 | 128.0 (3) | N2—C24—H24 | 117.9 |
C7—C8—H8 | 116.0 | C23—C24—H24 | 117.9 |
C17—C20—H20 | 117.4 | | |
Crystal data top
C14H12O3·2(C12H10N2) | Z = 2 |
Mr = 592.67 | F(000) = 624 |
Triclinic, P1 | Dx = 1.261 Mg m−3 |
a = 9.718 (3) Å | Mo Kα radiation, λ = 0.71073 Å |
b = 12.072 (4) Å | Cell parameters from 2497 reflections |
c = 15.426 (5) Å | θ = 2.5–25.1° |
α = 72.697 (4)° | µ = 0.08 mm−1 |
β = 72.681 (5)° | T = 220 K |
γ = 67.465 (6)° | Block, clear whiteish colourless |
V = 1560.9 (8) Å3 | 0.2 × 0.15 × 0.08 mm |
Data collection top
Bruker APEX-II CCD diffractometer | 3196 reflections with I > 2σ(I) |
ω scans | Rint = 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 = 0.746 | h = −10→11 |
10193 measured reflections | k = −12→14 |
5357 independent reflections | l = −18→18 |
Refinement top
Refinement on F2 | Primary atom site location: dual |
Least-squares matrix: full | Hydrogen site location: mixed |
R[F2 > 2σ(F2)] = 0.076 | H 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 reflections | Δρmax = 0.41 e Å−3 |
436 parameters | Δρmin = −0.39 e Å−3 |
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 | x | y | z | Uiso*/Ueq | Occ. (<1) |
O3 | 0.1818 (3) | 0.4689 (2) | 0.23593 (19) | 0.0597 (7) | |
O1 | 1.4001 (3) | −0.0064 (3) | 0.19658 (19) | 0.0607 (8) | |
O2 | 0.2864 (3) | 0.6208 (3) | 0.45601 (19) | 0.0669 (8) | |
N3 | 0.5590 (3) | 0.8017 (3) | 0.11591 (19) | 0.0472 (7) | |
N1 | 0.1042 (3) | 0.3554 (3) | 0.7201 (2) | 0.0586 (9) | |
N2 | 0.9988 (3) | −0.2183 (3) | 0.4647 (2) | 0.0588 (9) | |
C6 | 1.1532 (4) | 0.0068 (3) | 0.1833 (2) | 0.0440 (8) | |
H6 | 1.194634 | −0.064323 | 0.158570 | 0.053* | |
C1 | 1.2475 (3) | 0.0493 (3) | 0.2072 (2) | 0.0414 (8) | |
C29 | 0.8091 (3) | 0.6057 (3) | 0.0588 (2) | 0.0386 (8) | |
N4 | 0.7945 (4) | 0.0809 (3) | 0.0398 (2) | 0.0610 (9) | |
C4 | 0.9318 (3) | 0.1746 (3) | 0.2327 (2) | 0.0419 (8) | |
C9 | 0.5264 (3) | 0.3881 (3) | 0.3210 (2) | 0.0402 (8) | |
C32 | 0.9399 (4) | 0.4989 (3) | 0.0334 (2) | 0.0417 (8) | |
H32 | 0.936608 | 0.421289 | 0.068664 | 0.050* | |
C28 | 0.8001 (3) | 0.7267 (3) | 0.0158 (2) | 0.0433 (8) | |
H28 | 0.878276 | 0.744358 | −0.033355 | 0.052* | |
C13 | 0.2770 (3) | 0.4704 (3) | 0.2853 (2) | 0.0437 (8) | |
C35 | 0.6432 (4) | 0.3372 (3) | 0.0008 (2) | 0.0476 (8) | |
C8 | 0.6887 (4) | 0.3111 (3) | 0.3074 (2) | 0.0450 (8) | |
H8 | 0.744090 | 0.315152 | 0.346361 | 0.054* | |
C14 | 0.4255 (3) | 0.3900 (3) | 0.2711 (2) | 0.0442 (8) | |
H14 | 0.457698 | 0.338099 | 0.228971 | 0.053* | |
C7 | 0.7669 (3) | 0.2376 (3) | 0.2486 (2) | 0.0446 (8) | |
H7 | 0.712089 | 0.224394 | 0.213757 | 0.054* | |
C5 | 0.9977 (4) | 0.0686 (3) | 0.1958 (2) | 0.0452 (8) | |
H5 | 0.935220 | 0.038672 | 0.179074 | 0.054* | |
C10 | 0.4775 (3) | 0.4653 (3) | 0.3827 (2) | 0.0467 (9) | |
H10 | 0.544783 | 0.463826 | 0.416271 | 0.056* | |
C11 | 0.3276 (4) | 0.5453 (3) | 0.3950 (2) | 0.0474 (9) | |
C34 | 0.5654 (4) | 0.2540 (3) | 0.0528 (3) | 0.0519 (9) | |
H34 | 0.459971 | 0.282383 | 0.076484 | 0.062* | |
C12 | 0.2288 (3) | 0.5477 (3) | 0.3462 (2) | 0.0446 (8) | |
H12 | 0.128392 | 0.602061 | 0.354349 | 0.054* | |
C3 | 1.0306 (4) | 0.2175 (3) | 0.2538 (2) | 0.0459 (8) | |
H3A | 0.990283 | 0.289709 | 0.277154 | 0.055* | |
C17 | 0.3686 (4) | 0.1830 (4) | 0.6443 (3) | 0.0606 (11) | |
C36 | 0.7998 (4) | 0.2841 (3) | −0.0303 (3) | 0.0540 (9) | |
H36 | 0.858910 | 0.334648 | −0.065437 | 0.065* | |
C2 | 1.1862 (4) | 0.1564 (3) | 0.2411 (2) | 0.0536 (10) | |
H2A | 1.249976 | 0.187492 | 0.255448 | 0.064* | |
C31 | 0.5672 (4) | 0.6856 (4) | 0.1552 (2) | 0.0565 (10) | |
H31 | 0.485402 | 0.670457 | 0.202384 | 0.068* | |
C30 | 0.6884 (4) | 0.5871 (3) | 0.1304 (2) | 0.0513 (9) | |
H30 | 0.689915 | 0.507071 | 0.161798 | 0.062* | |
C27 | 0.6748 (4) | 0.8204 (3) | 0.0464 (2) | 0.0485 (9) | |
H27 | 0.670344 | 0.901566 | 0.017028 | 0.058* | |
C37 | 0.8678 (4) | 0.1605 (4) | −0.0106 (3) | 0.0614 (10) | |
H37 | 0.972988 | 0.129076 | −0.033853 | 0.074* | |
C38 | 0.5715 (4) | 0.4714 (3) | −0.0184 (2) | 0.0501 (9) | |
H38 | 0.630636 | 0.519394 | −0.059154 | 0.060* | |
C23 | 0.7439 (5) | −0.1646 (5) | 0.5533 (3) | 0.0773 (14) | |
H23 | 0.663608 | −0.191004 | 0.593832 | 0.093* | |
C24 | 0.8812 (5) | −0.2503 (4) | 0.5227 (3) | 0.0653 (11) | |
H24 | 0.891656 | −0.334059 | 0.543769 | 0.078* | |
C33 | 0.6442 (4) | 0.1313 (4) | 0.0687 (3) | 0.0614 (10) | |
H33 | 0.588308 | 0.077887 | 0.102654 | 0.074* | |
C22 | 0.7246 (5) | −0.0401 (5) | 0.5243 (3) | 0.0759 (15) | |
C25 | 0.9768 (5) | −0.0993 (4) | 0.4342 (3) | 0.0654 (11) | |
H25 | 1.056544 | −0.074655 | 0.391039 | 0.079* | |
C26 | 0.8440 (6) | −0.0092 (4) | 0.4621 (3) | 0.0753 (13) | |
H26 | 0.835807 | 0.073829 | 0.438075 | 0.090* | |
C15 | 0.2140 (5) | 0.3888 (4) | 0.6543 (3) | 0.0738 (12) | |
H15 | 0.200965 | 0.472879 | 0.632551 | 0.089* | |
C19 | 0.1293 (5) | 0.2359 (4) | 0.7463 (3) | 0.0816 (15) | |
H19 | 0.053618 | 0.208485 | 0.791700 | 0.098* | |
C16 | 0.3454 (5) | 0.3065 (5) | 0.6166 (3) | 0.0816 (14) | |
H16 | 0.420187 | 0.335185 | 0.571311 | 0.098* | |
C18 | 0.2574 (5) | 0.1497 (4) | 0.7119 (4) | 0.0866 (15) | |
H18 | 0.268630 | 0.066108 | 0.735422 | 0.104* | |
C20 | 0.4929 (8) | 0.0695 (9) | 0.6184 (5) | 0.0506 (17) | 0.6 |
H20 | 0.488837 | −0.007740 | 0.653956 | 0.061* | 0.6 |
C21 | 0.6056 (7) | 0.0756 (9) | 0.5482 (4) | 0.0554 (18) | 0.6 |
H21 | 0.612405 | 0.152157 | 0.512651 | 0.066* | 0.6 |
C1AA | 0.5667 (11) | 0.0065 (10) | 0.5817 (7) | 0.043 (2) | 0.4 |
H1AA | 0.504467 | −0.042753 | 0.613119 | 0.052* | 0.4 |
C0AA | 0.5249 (12) | 0.1251 (10) | 0.5832 (10) | 0.044 (2) | 0.4 |
H0AA | 0.588382 | 0.172250 | 0.548187 | 0.052* | 0.4 |
H1 | 1.416 (4) | −0.063 (3) | 0.169 (3) | 0.066 (13)* | |
H3 | 0.092 (3) | 0.522 (3) | 0.253 (3) | 0.082 (14)* | |
H2 | 0.192 (3) | 0.668 (3) | 0.463 (3) | 0.078 (13)* | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
O3 | 0.0356 (13) | 0.0656 (18) | 0.0845 (18) | −0.0041 (12) | −0.0104 (13) | −0.0436 (14) |
O1 | 0.0293 (12) | 0.0715 (19) | 0.0819 (18) | −0.0019 (12) | −0.0035 (12) | −0.0441 (15) |
O2 | 0.0394 (14) | 0.081 (2) | 0.0796 (18) | 0.0109 (13) | −0.0195 (13) | −0.0497 (15) |
N3 | 0.0376 (15) | 0.0456 (18) | 0.0518 (16) | −0.0035 (12) | −0.0034 (12) | −0.0198 (13) |
N1 | 0.0355 (15) | 0.074 (2) | 0.071 (2) | −0.0076 (15) | −0.0069 (14) | −0.0392 (17) |
N2 | 0.0411 (17) | 0.064 (2) | 0.0601 (18) | 0.0031 (15) | −0.0059 (14) | −0.0281 (16) |
C6 | 0.0389 (17) | 0.0345 (17) | 0.0546 (19) | −0.0073 (14) | 0.0033 (15) | −0.0225 (14) |
C1 | 0.0274 (15) | 0.0451 (19) | 0.0458 (17) | −0.0043 (13) | 0.0000 (13) | −0.0185 (14) |
C29 | 0.0365 (17) | 0.0363 (18) | 0.0437 (16) | −0.0086 (13) | −0.0051 (13) | −0.0165 (13) |
N4 | 0.0562 (19) | 0.0493 (19) | 0.080 (2) | −0.0093 (15) | −0.0139 (17) | −0.0283 (16) |
C4 | 0.0328 (16) | 0.0374 (18) | 0.0500 (18) | −0.0082 (13) | −0.0032 (14) | −0.0107 (14) |
C9 | 0.0298 (16) | 0.0355 (17) | 0.0443 (16) | −0.0035 (13) | −0.0035 (13) | −0.0063 (13) |
C32 | 0.0432 (17) | 0.0279 (16) | 0.0485 (18) | −0.0053 (14) | −0.0079 (13) | −0.0100 (13) |
C28 | 0.0366 (17) | 0.0379 (19) | 0.0521 (18) | −0.0099 (14) | 0.0024 (14) | −0.0191 (15) |
C13 | 0.0300 (16) | 0.0470 (19) | 0.0528 (19) | −0.0108 (14) | −0.0020 (14) | −0.0174 (15) |
C35 | 0.0479 (19) | 0.047 (2) | 0.0551 (19) | −0.0130 (16) | −0.0130 (16) | −0.0220 (16) |
C8 | 0.0302 (16) | 0.049 (2) | 0.0463 (17) | −0.0052 (14) | −0.0048 (13) | −0.0103 (15) |
C14 | 0.0337 (16) | 0.0407 (19) | 0.0497 (18) | −0.0027 (14) | −0.0038 (14) | −0.0149 (15) |
C7 | 0.0304 (16) | 0.0428 (19) | 0.0561 (19) | −0.0069 (14) | −0.0069 (14) | −0.0127 (15) |
C5 | 0.0365 (17) | 0.0445 (19) | 0.0544 (19) | −0.0124 (14) | −0.0046 (14) | −0.0157 (15) |
C10 | 0.0298 (16) | 0.058 (2) | 0.0484 (18) | −0.0070 (15) | −0.0059 (14) | −0.0166 (16) |
C11 | 0.0354 (17) | 0.050 (2) | 0.0505 (19) | −0.0016 (15) | −0.0054 (15) | −0.0218 (16) |
C34 | 0.0459 (19) | 0.047 (2) | 0.073 (2) | −0.0155 (16) | −0.0108 (17) | −0.0272 (18) |
C12 | 0.0268 (15) | 0.048 (2) | 0.0543 (19) | −0.0005 (13) | −0.0085 (14) | −0.0197 (15) |
C3 | 0.0405 (18) | 0.0414 (19) | 0.0559 (19) | −0.0059 (14) | −0.0014 (15) | −0.0286 (15) |
C17 | 0.0371 (19) | 0.079 (3) | 0.065 (2) | 0.0050 (18) | −0.0181 (18) | −0.037 (2) |
C36 | 0.0442 (19) | 0.051 (2) | 0.064 (2) | −0.0129 (16) | −0.0052 (17) | −0.0178 (17) |
C2 | 0.0355 (17) | 0.067 (2) | 0.066 (2) | −0.0129 (16) | −0.0015 (16) | −0.0387 (19) |
C31 | 0.0396 (18) | 0.061 (2) | 0.055 (2) | −0.0106 (17) | 0.0057 (16) | −0.0161 (18) |
C30 | 0.049 (2) | 0.0358 (19) | 0.055 (2) | −0.0107 (15) | −0.0004 (16) | −0.0039 (15) |
C27 | 0.0395 (17) | 0.0376 (19) | 0.065 (2) | −0.0069 (14) | −0.0036 (16) | −0.0211 (16) |
C37 | 0.049 (2) | 0.054 (2) | 0.078 (3) | −0.0073 (18) | −0.0065 (19) | −0.027 (2) |
C38 | 0.0453 (18) | 0.050 (2) | 0.060 (2) | −0.0130 (15) | −0.0099 (16) | −0.0226 (16) |
C23 | 0.044 (2) | 0.124 (4) | 0.054 (2) | −0.024 (2) | 0.0004 (18) | −0.019 (2) |
C24 | 0.059 (2) | 0.063 (3) | 0.070 (2) | −0.014 (2) | −0.016 (2) | −0.012 (2) |
C33 | 0.057 (2) | 0.056 (2) | 0.081 (3) | −0.0243 (19) | −0.014 (2) | −0.021 (2) |
C22 | 0.059 (3) | 0.095 (4) | 0.054 (2) | 0.022 (2) | −0.022 (2) | −0.038 (2) |
C25 | 0.062 (2) | 0.066 (3) | 0.054 (2) | −0.014 (2) | 0.0011 (19) | −0.0143 (19) |
C26 | 0.095 (3) | 0.049 (2) | 0.069 (3) | 0.005 (2) | −0.034 (3) | −0.013 (2) |
C15 | 0.056 (2) | 0.056 (3) | 0.105 (3) | −0.016 (2) | −0.006 (2) | −0.023 (2) |
C19 | 0.047 (2) | 0.074 (3) | 0.096 (3) | −0.018 (2) | 0.014 (2) | −0.010 (3) |
C16 | 0.050 (2) | 0.090 (4) | 0.086 (3) | −0.021 (2) | 0.019 (2) | −0.025 (3) |
C18 | 0.059 (3) | 0.054 (3) | 0.117 (4) | −0.005 (2) | −0.007 (3) | −0.004 (2) |
C20 | 0.043 (4) | 0.043 (5) | 0.058 (4) | −0.006 (4) | −0.012 (3) | −0.009 (4) |
C21 | 0.044 (4) | 0.051 (4) | 0.048 (4) | 0.003 (4) | −0.002 (3) | −0.009 (3) |
C1AA | 0.030 (4) | 0.042 (5) | 0.047 (5) | −0.005 (5) | −0.006 (4) | −0.007 (5) |
C0AA | 0.031 (5) | 0.036 (6) | 0.069 (7) | −0.013 (5) | −0.005 (5) | −0.021 (6) |
Geometric parameters (Å, º) top
O3—C13 | 1.371 (4) | C11—C12 | 1.373 (5) |
O3—H3 | 0.881 (19) | C34—H34 | 0.9400 |
O1—C1 | 1.354 (4) | C34—C33 | 1.366 (5) |
O1—H1 | 0.853 (19) | C12—H12 | 0.9400 |
O2—C11 | 1.371 (4) | C3—H3A | 0.9400 |
O2—H2 | 0.870 (19) | C3—C2 | 1.387 (4) |
N3—C31 | 1.332 (5) | C17—C16 | 1.370 (7) |
N3—C27 | 1.341 (4) | C17—C18 | 1.352 (6) |
N1—C15 | 1.332 (5) | C17—C20 | 1.505 (9) |
N1—C19 | 1.322 (5) | C17—C0AA | 1.553 (13) |
N2—C24 | 1.334 (5) | C36—H36 | 0.9400 |
N2—C25 | 1.325 (5) | C36—C37 | 1.360 (5) |
C6—H6 | 0.9400 | C2—H2A | 0.9400 |
C6—C1 | 1.383 (5) | C31—H31 | 0.9400 |
C6—C5 | 1.388 (4) | C31—C30 | 1.369 (5) |
C1—C2 | 1.388 (5) | C30—H30 | 0.9400 |
C29—C32 | 1.477 (4) | C27—H27 | 0.9400 |
C29—C28 | 1.393 (5) | C37—H37 | 0.9400 |
C29—C30 | 1.389 (4) | C38—C38ii | 1.326 (6) |
N4—C37 | 1.336 (5) | C38—H38 | 0.9400 |
N4—C33 | 1.340 (5) | C23—H23 | 0.9400 |
C4—C7 | 1.466 (4) | C23—C24 | 1.390 (6) |
C4—C5 | 1.400 (5) | C23—C22 | 1.389 (7) |
C4—C3 | 1.401 (5) | C24—H24 | 0.9400 |
C9—C8 | 1.480 (4) | C33—H33 | 0.9400 |
C9—C14 | 1.406 (5) | C22—C26 | 1.365 (7) |
C9—C10 | 1.385 (5) | C22—C21 | 1.496 (9) |
C32—C32i | 1.310 (6) | C22—C1AA | 1.511 (11) |
C32—H32 | 0.9400 | C25—H25 | 0.9400 |
C28—H28 | 0.9400 | C25—C26 | 1.380 (6) |
C28—C27 | 1.379 (4) | C26—H26 | 0.9400 |
C13—C14 | 1.392 (4) | C15—H15 | 0.9400 |
C13—C12 | 1.377 (5) | C15—C16 | 1.372 (6) |
C35—C34 | 1.402 (5) | C19—H19 | 0.9400 |
C35—C36 | 1.399 (5) | C19—C18 | 1.362 (6) |
C35—C38 | 1.474 (5) | C16—H16 | 0.9400 |
C8—H8 | 0.9400 | C18—H18 | 0.9400 |
C8—C7 | 1.319 (5) | C20—H20 | 0.9400 |
C14—H14 | 0.9400 | C20—C21 | 1.298 (9) |
C7—H7 | 0.9400 | C21—H21 | 0.9400 |
C5—H5 | 0.9400 | C1AA—H1AA | 0.9400 |
C10—H10 | 0.9400 | C1AA—C0AA | 1.336 (15) |
C10—C11 | 1.399 (4) | C0AA—H0AA | 0.9400 |
| | | |
C13—O3—H3 | 107 (3) | C35—C36—H36 | 119.5 |
C1—O1—H1 | 103 (3) | C37—C36—C35 | 121.1 (4) |
C11—O2—H2 | 115 (3) | C37—C36—H36 | 119.5 |
C31—N3—C27 | 116.9 (3) | C1—C2—H2A | 120.1 |
C19—N1—C15 | 115.0 (3) | C3—C2—C1 | 119.9 (3) |
C25—N2—C24 | 116.6 (3) | C3—C2—H2A | 120.1 |
C1—C6—H6 | 119.9 | N3—C31—H31 | 118.2 |
C1—C6—C5 | 120.3 (3) | N3—C31—C30 | 123.6 (3) |
C5—C6—H6 | 119.9 | C30—C31—H31 | 118.2 |
O1—C1—C6 | 123.3 (3) | C29—C30—H30 | 120.1 |
O1—C1—C2 | 117.2 (3) | C31—C30—C29 | 119.9 (3) |
C6—C1—C2 | 119.5 (3) | C31—C30—H30 | 120.1 |
C28—C29—C32 | 123.6 (3) | N3—C27—C28 | 123.5 (3) |
C30—C29—C32 | 119.4 (3) | N3—C27—H27 | 118.2 |
C30—C29—C28 | 117.0 (3) | C28—C27—H27 | 118.2 |
C37—N4—C33 | 114.9 (3) | N4—C37—C36 | 124.1 (3) |
C5—C4—C7 | 121.4 (3) | N4—C37—H37 | 117.9 |
C5—C4—C3 | 116.9 (3) | C36—C37—H37 | 117.9 |
C3—C4—C7 | 121.6 (3) | C35—C38—H38 | 118.1 |
C14—C9—C8 | 122.9 (3) | C38ii—C38—C35 | 123.8 (5) |
C10—C9—C8 | 116.9 (3) | C38ii—C38—H38 | 118.1 |
C10—C9—C14 | 120.1 (3) | C24—C23—H23 | 119.8 |
C29—C32—H32 | 116.7 | C22—C23—H23 | 119.8 |
C32i—C32—C29 | 126.6 (4) | C22—C23—C24 | 120.4 (4) |
C32i—C32—H32 | 116.7 | N2—C24—C23 | 122.5 (4) |
C29—C28—H28 | 120.4 | N2—C24—H24 | 118.7 |
C27—C28—C29 | 119.1 (3) | C23—C24—H24 | 118.7 |
C27—C28—H28 | 120.4 | N4—C33—C34 | 125.4 (4) |
O3—C13—C14 | 116.9 (3) | N4—C33—H33 | 117.3 |
O3—C13—C12 | 121.8 (3) | C34—C33—H33 | 117.3 |
C12—C13—C14 | 121.3 (3) | C23—C22—C21 | 136.1 (5) |
C34—C35—C38 | 124.3 (3) | C23—C22—C1AA | 97.9 (6) |
C36—C35—C34 | 115.0 (3) | C26—C22—C23 | 116.1 (4) |
C36—C35—C38 | 120.6 (3) | C26—C22—C21 | 107.7 (5) |
C9—C8—H8 | 115.3 | C26—C22—C1AA | 146.0 (6) |
C7—C8—C9 | 129.4 (3) | N2—C25—H25 | 118.0 |
C7—C8—H8 | 115.3 | N2—C25—C26 | 124.0 (4) |
C9—C14—H14 | 120.7 | C26—C25—H25 | 118.0 |
C13—C14—C9 | 118.6 (3) | C22—C26—C25 | 120.3 (4) |
C13—C14—H14 | 120.7 | C22—C26—H26 | 119.8 |
C4—C7—H7 | 117.1 | C25—C26—H26 | 119.8 |
C8—C7—C4 | 125.7 (3) | N1—C15—H15 | 118.3 |
C8—C7—H7 | 117.1 | N1—C15—C16 | 123.3 (4) |
C6—C5—C4 | 121.5 (3) | C16—C15—H15 | 118.3 |
C6—C5—H5 | 119.2 | N1—C19—H19 | 117.8 |
C4—C5—H5 | 119.2 | N1—C19—C18 | 124.5 (4) |
C9—C10—H10 | 120.1 | C18—C19—H19 | 117.8 |
C9—C10—C11 | 119.9 (3) | C17—C16—C15 | 120.7 (4) |
C11—C10—H10 | 120.1 | C17—C16—H16 | 119.6 |
O2—C11—C10 | 117.2 (3) | C15—C16—H16 | 119.6 |
O2—C11—C12 | 122.5 (3) | C17—C18—C19 | 120.8 (4) |
C12—C11—C10 | 120.3 (3) | C17—C18—H18 | 119.6 |
C35—C34—H34 | 120.3 | C19—C18—H18 | 119.6 |
C33—C34—C35 | 119.4 (3) | C17—C20—H20 | 119.1 |
C33—C34—H34 | 120.3 | C21—C20—C17 | 121.7 (10) |
C13—C12—H12 | 120.0 | C21—C20—H20 | 119.1 |
C11—C12—C13 | 119.9 (3) | C22—C21—H21 | 120.2 |
C11—C12—H12 | 120.0 | C20—C21—C22 | 119.6 (9) |
C4—C3—H3A | 119.1 | C20—C21—H21 | 120.2 |
C2—C3—C4 | 121.8 (3) | C22—C1AA—H1AA | 123.6 |
C2—C3—H3A | 119.1 | C0AA—C1AA—C22 | 112.8 (12) |
C16—C17—C20 | 135.3 (5) | C0AA—C1AA—H1AA | 123.6 |
C16—C17—C0AA | 103.9 (6) | C17—C0AA—H0AA | 120.9 |
C18—C17—C16 | 115.7 (4) | C1AA—C0AA—C17 | 118.1 (12) |
C18—C17—C20 | 109.1 (5) | C1AA—C0AA—H0AA | 120.9 |
C18—C17—C0AA | 140.4 (6) | | |
Symmetry codes: (i) −x+2, −y+1, −z; (ii) −x+1, −y+1, −z. |
Crystal data top
C14H12O3·2(C6H5N) | F(000) = 864 |
Mr = 410.45 | Dx = 1.341 Mg m−3 |
Monoclinic, P21/c | Mo Kα radiation, λ = 0.71073 Å |
a = 24.4184 (16) Å | Cell parameters from 4351 reflections |
b = 6.5303 (4) Å | θ = 3.2–23.6° |
c = 12.7495 (8) Å | µ = 0.09 mm−1 |
β = 90.172 (4)° | T = 230 K |
V = 2033.0 (2) Å3 | Block, clear yellowish yellow |
Z = 4 | 0.19 × 0.11 × 0.08 mm |
Data collection top
Bruker APEX-II CCD diffractometer | 3156 reflections with I > 2σ(I) |
ω scans | Rint = 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 = 0.991 | h = −31→31 |
28343 measured reflections | k = −8→8 |
4682 independent reflections | l = −16→16 |
Refinement top
Refinement on F2 | Primary atom site location: dual |
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) = 0.121 | w = 1/[σ2(Fo2) + (0.0548P)2 + 0.0935P] where P = (Fo2 + 2Fc2)/3 |
S = 1.04 | (Δ/σ)max = 0.001 |
4682 reflections | Δρmax = 0.16 e Å−3 |
301 parameters | Δρmin = −0.27 e Å−3 |
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 | x | y | z | Uiso*/Ueq | Occ. (<1) |
O1 | 0.12413 (5) | 0.2452 (2) | 0.36281 (9) | 0.0421 (3) | |
O3 | 0.37555 (5) | 1.05969 (17) | 0.97733 (10) | 0.0453 (3) | |
O2 | 0.32749 (5) | 0.4053 (2) | 1.10909 (9) | 0.0454 (3) | |
N1 | 0.44309 (5) | 0.44638 (19) | 0.64889 (10) | 0.0325 (3) | |
N2 | 0.91339 (6) | 0.0680 (2) | 0.25515 (11) | 0.0429 (4) | |
C20 | 0.51344 (6) | 0.4965 (2) | 0.95487 (11) | 0.0284 (3) | |
H20 | 0.551805 | 0.506981 | 0.958128 | 0.034* | |
C17 | 0.48878 (6) | 0.4740 (2) | 0.85075 (11) | 0.0258 (3) | |
C9 | 0.29402 (6) | 0.6534 (2) | 0.85800 (11) | 0.0277 (3) | |
C18 | 0.43265 (6) | 0.4508 (2) | 0.83554 (12) | 0.0301 (4) | |
H18 | 0.408948 | 0.443942 | 0.893390 | 0.036* | |
C11 | 0.32386 (6) | 0.5454 (2) | 1.02896 (12) | 0.0298 (3) | |
C16 | 0.52122 (6) | 0.4770 (2) | 0.76107 (12) | 0.0286 (3) | |
H16 | 0.559489 | 0.487542 | 0.767184 | 0.034* | |
C1 | 0.15489 (6) | 0.2965 (3) | 0.44784 (12) | 0.0314 (4) | |
C15 | 0.49716 (6) | 0.4644 (2) | 0.66348 (12) | 0.0306 (4) | |
H15 | 0.519870 | 0.468665 | 0.604114 | 0.037* | |
C13 | 0.34959 (6) | 0.8758 (2) | 0.96586 (12) | 0.0307 (4) | |
C12 | 0.35084 (6) | 0.7295 (2) | 1.04445 (12) | 0.0294 (3) | |
H12 | 0.369748 | 0.754870 | 1.107460 | 0.035* | |
C8 | 0.26542 (6) | 0.6158 (3) | 0.75827 (12) | 0.0315 (4) | |
H8 | 0.262297 | 0.726881 | 0.711735 | 0.038* | |
C14 | 0.32128 (6) | 0.8383 (2) | 0.87318 (12) | 0.0311 (4) | |
H14 | 0.320519 | 0.938562 | 0.820293 | 0.037* | |
C4 | 0.21512 (6) | 0.3939 (3) | 0.62937 (12) | 0.0315 (4) | |
C10 | 0.29527 (6) | 0.5057 (2) | 0.93791 (12) | 0.0300 (4) | |
H10 | 0.276736 | 0.380611 | 0.929373 | 0.036* | |
C7 | 0.24353 (6) | 0.4387 (3) | 0.72785 (12) | 0.0339 (4) | |
H7 | 0.246716 | 0.329357 | 0.775405 | 0.041* | |
C5 | 0.21042 (6) | 0.5326 (3) | 0.54629 (12) | 0.0346 (4) | |
H5 | 0.227666 | 0.660900 | 0.551305 | 0.042* | |
C19 | 0.41225 (6) | 0.4381 (2) | 0.73557 (12) | 0.0332 (4) | |
H19 | 0.374212 | 0.422638 | 0.727224 | 0.040* | |
C3 | 0.19020 (6) | 0.2029 (3) | 0.61646 (12) | 0.0349 (4) | |
H3A | 0.193877 | 0.104399 | 0.669762 | 0.042* | |
C6 | 0.18100 (6) | 0.4848 (3) | 0.45722 (13) | 0.0362 (4) | |
H6 | 0.178565 | 0.580393 | 0.402282 | 0.043* | |
C2 | 0.16026 (6) | 0.1546 (3) | 0.52747 (13) | 0.0347 (4) | |
H2A | 0.143610 | 0.025380 | 0.521277 | 0.042* | |
C25 | 0.95751 (7) | 0.0084 (3) | 0.30793 (14) | 0.0460 (5) | |
H25 | 0.970875 | −0.124590 | 0.296138 | 0.055* | |
C21 | 0.89562 (7) | 0.2574 (3) | 0.27439 (17) | 0.0537 (5) | |
H21 | 0.864775 | 0.304440 | 0.237258 | 0.064* | |
C24 | 0.98461 (8) | 0.1295 (4) | 0.37847 (16) | 0.0624 (6) | |
H24 | 1.016198 | 0.080425 | 0.412499 | 0.075* | |
C23 | 0.96535 (10) | 0.3250 (4) | 0.39968 (16) | 0.0710 (8) | |
C22 | 0.91961 (9) | 0.3866 (4) | 0.34481 (19) | 0.0672 (7) | |
H22 | 0.904903 | 0.517789 | 0.355897 | 0.081* | |
C26A | 1.00612 (17) | 0.4094 (6) | 0.4793 (3) | 0.0373 (8) | 0.5 |
H26A | 1.038048 | 0.337621 | 0.498048 | 0.045* | 0.5 |
C26B | 0.02241 (14) | 0.4922 (7) | 0.5290 (3) | 0.0390 (8) | 0.5 |
H26B | 0.045238 | 0.376415 | 0.526466 | 0.047* | 0.5 |
H3 | 0.4005 (8) | 1.057 (4) | 1.0295 (16) | 0.093 (8)* | |
H1 | 0.1161 (10) | 0.358 (3) | 0.3271 (18) | 0.094 (9)* | |
H2 | 0.3148 (10) | 0.294 (3) | 1.085 (2) | 0.111 (10)* | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
O1 | 0.0441 (7) | 0.0497 (8) | 0.0325 (7) | −0.0037 (6) | −0.0178 (5) | −0.0029 (6) |
O3 | 0.0593 (8) | 0.0316 (7) | 0.0450 (8) | −0.0118 (6) | −0.0214 (6) | 0.0033 (6) |
O2 | 0.0648 (8) | 0.0389 (7) | 0.0324 (7) | −0.0095 (6) | −0.0156 (6) | 0.0085 (6) |
N1 | 0.0404 (8) | 0.0303 (7) | 0.0266 (7) | 0.0062 (6) | −0.0078 (6) | −0.0014 (6) |
N2 | 0.0387 (8) | 0.0531 (10) | 0.0371 (9) | −0.0046 (7) | −0.0055 (6) | −0.0084 (7) |
C20 | 0.0272 (8) | 0.0300 (8) | 0.0280 (8) | 0.0007 (6) | −0.0071 (6) | 0.0010 (6) |
C17 | 0.0296 (7) | 0.0209 (7) | 0.0269 (8) | 0.0019 (6) | −0.0046 (6) | 0.0016 (6) |
C9 | 0.0245 (7) | 0.0356 (9) | 0.0229 (8) | 0.0029 (6) | −0.0030 (6) | −0.0032 (7) |
C18 | 0.0293 (8) | 0.0338 (9) | 0.0272 (8) | 0.0032 (6) | −0.0012 (6) | −0.0017 (7) |
C11 | 0.0318 (8) | 0.0335 (9) | 0.0239 (8) | 0.0025 (7) | −0.0028 (6) | 0.0014 (7) |
C16 | 0.0310 (8) | 0.0238 (7) | 0.0310 (9) | 0.0007 (6) | −0.0025 (7) | 0.0014 (6) |
C1 | 0.0254 (7) | 0.0434 (10) | 0.0253 (8) | 0.0008 (7) | −0.0060 (6) | −0.0042 (7) |
C15 | 0.0381 (9) | 0.0260 (8) | 0.0278 (9) | 0.0036 (6) | 0.0000 (7) | 0.0005 (6) |
C13 | 0.0309 (8) | 0.0290 (8) | 0.0321 (9) | 0.0005 (6) | −0.0049 (7) | −0.0032 (7) |
C12 | 0.0303 (8) | 0.0339 (9) | 0.0238 (8) | 0.0033 (6) | −0.0070 (6) | −0.0063 (7) |
C8 | 0.0286 (8) | 0.0408 (9) | 0.0250 (8) | 0.0003 (7) | −0.0040 (6) | 0.0010 (7) |
C14 | 0.0331 (8) | 0.0331 (9) | 0.0271 (8) | 0.0022 (7) | −0.0046 (7) | 0.0017 (7) |
C4 | 0.0282 (8) | 0.0415 (9) | 0.0249 (8) | −0.0017 (7) | −0.0034 (6) | −0.0009 (7) |
C10 | 0.0296 (8) | 0.0330 (9) | 0.0275 (8) | −0.0035 (6) | −0.0025 (6) | −0.0026 (7) |
C7 | 0.0327 (8) | 0.0430 (10) | 0.0260 (8) | −0.0012 (7) | −0.0055 (7) | 0.0012 (7) |
C5 | 0.0323 (8) | 0.0414 (9) | 0.0302 (9) | −0.0084 (7) | −0.0058 (7) | 0.0029 (7) |
C19 | 0.0307 (8) | 0.0358 (9) | 0.0331 (9) | 0.0040 (7) | −0.0069 (7) | −0.0017 (7) |
C3 | 0.0388 (9) | 0.0387 (9) | 0.0272 (9) | −0.0018 (7) | −0.0055 (7) | 0.0051 (7) |
C6 | 0.0361 (9) | 0.0449 (10) | 0.0275 (9) | −0.0057 (7) | −0.0068 (7) | 0.0066 (7) |
C2 | 0.0343 (8) | 0.0366 (9) | 0.0332 (9) | −0.0045 (7) | −0.0054 (7) | −0.0007 (7) |
C25 | 0.0417 (10) | 0.0579 (12) | 0.0383 (11) | −0.0023 (8) | −0.0004 (8) | 0.0011 (9) |
C21 | 0.0395 (10) | 0.0544 (12) | 0.0673 (14) | 0.0001 (9) | −0.0021 (9) | −0.0113 (11) |
C24 | 0.0505 (12) | 0.0981 (19) | 0.0386 (11) | −0.0295 (12) | −0.0142 (9) | 0.0132 (12) |
C23 | 0.0810 (16) | 0.098 (2) | 0.0344 (12) | −0.0572 (15) | 0.0127 (11) | −0.0178 (12) |
C22 | 0.0662 (14) | 0.0601 (14) | 0.0755 (16) | −0.0204 (11) | 0.0255 (13) | −0.0312 (12) |
C26A | 0.0253 (18) | 0.049 (2) | 0.038 (2) | 0.0024 (19) | −0.0038 (16) | −0.0102 (19) |
C26B | 0.036 (2) | 0.043 (2) | 0.038 (2) | 0.006 (2) | −0.0026 (17) | −0.0062 (19) |
Geometric parameters (Å, º) top
O1—C1 | 1.3590 (18) | C8—H8 | 0.9400 |
O1—H1 | 0.887 (16) | C8—C7 | 1.331 (2) |
O3—C13 | 1.3657 (19) | C14—H14 | 0.9400 |
O3—H3 | 0.901 (16) | C4—C7 | 1.462 (2) |
O2—C11 | 1.3742 (19) | C4—C5 | 1.398 (2) |
O2—H2 | 0.847 (17) | C4—C3 | 1.397 (2) |
N1—C15 | 1.3380 (19) | C10—H10 | 0.9400 |
N1—C19 | 1.340 (2) | C7—H7 | 0.9400 |
N2—C25 | 1.327 (2) | C5—H5 | 0.9400 |
N2—C21 | 1.333 (2) | C5—C6 | 1.378 (2) |
C20—C20i | 1.327 (3) | C19—H19 | 0.9400 |
C20—H20 | 0.9400 | C3—H3A | 0.9400 |
C20—C17 | 1.464 (2) | C3—C2 | 1.384 (2) |
C17—C18 | 1.392 (2) | C6—H6 | 0.9400 |
C17—C16 | 1.393 (2) | C2—H2A | 0.9400 |
C9—C8 | 1.470 (2) | C25—H25 | 0.9400 |
C9—C14 | 1.392 (2) | C25—C24 | 1.367 (3) |
C9—C10 | 1.403 (2) | C21—H21 | 0.9400 |
C18—H18 | 0.9400 | C21—C22 | 1.363 (3) |
C18—C19 | 1.370 (2) | C24—H24 | 0.9400 |
C11—C12 | 1.385 (2) | C24—C23 | 1.388 (3) |
C11—C10 | 1.377 (2) | C23—C22 | 1.376 (3) |
C16—H16 | 0.9400 | C23—C26A | 1.523 (5) |
C16—C15 | 1.377 (2) | C23—C26Bii | 1.530 (5) |
C1—C6 | 1.390 (2) | C22—H22 | 0.9400 |
C1—C2 | 1.380 (2) | C26A—C26Aiii | 1.330 (7) |
C15—H15 | 0.9400 | C26A—H26A | 0.9400 |
C13—C12 | 1.384 (2) | C26B—C26Biv | 1.322 (7) |
C13—C14 | 1.389 (2) | C26B—H26B | 0.9400 |
C12—H12 | 0.9400 | | |
| | | |
C1—O1—H1 | 108.9 (17) | C9—C10—H10 | 120.3 |
C13—O3—H3 | 112.0 (16) | C11—C10—C9 | 119.49 (14) |
C11—O2—H2 | 106.1 (19) | C11—C10—H10 | 120.3 |
C15—N1—C19 | 116.47 (13) | C8—C7—C4 | 127.82 (16) |
C25—N2—C21 | 116.30 (16) | C8—C7—H7 | 116.1 |
C20i—C20—H20 | 117.0 | C4—C7—H7 | 116.1 |
C20i—C20—C17 | 125.91 (18) | C4—C5—H5 | 119.4 |
C17—C20—H20 | 117.0 | C6—C5—C4 | 121.28 (15) |
C18—C17—C20 | 122.66 (13) | C6—C5—H5 | 119.4 |
C18—C17—C16 | 116.70 (14) | N1—C19—C18 | 124.13 (14) |
C16—C17—C20 | 120.63 (13) | N1—C19—H19 | 117.9 |
C14—C9—C8 | 119.41 (14) | C18—C19—H19 | 117.9 |
C14—C9—C10 | 119.08 (14) | C4—C3—H3A | 119.0 |
C10—C9—C8 | 121.50 (14) | C2—C3—C4 | 121.92 (15) |
C17—C18—H18 | 120.3 | C2—C3—H3A | 119.0 |
C19—C18—C17 | 119.44 (14) | C1—C6—H6 | 119.7 |
C19—C18—H18 | 120.3 | C5—C6—C1 | 120.60 (15) |
O2—C11—C12 | 116.26 (14) | C5—C6—H6 | 119.7 |
O2—C11—C10 | 122.19 (14) | C1—C2—C3 | 119.90 (15) |
C10—C11—C12 | 121.56 (14) | C1—C2—H2A | 120.0 |
C17—C16—H16 | 120.0 | C3—C2—H2A | 120.0 |
C15—C16—C17 | 119.92 (14) | N2—C25—H25 | 118.2 |
C15—C16—H16 | 120.0 | N2—C25—C24 | 123.7 (2) |
O1—C1—C6 | 122.61 (15) | C24—C25—H25 | 118.2 |
O1—C1—C2 | 118.18 (15) | N2—C21—H21 | 118.1 |
C2—C1—C6 | 119.20 (15) | N2—C21—C22 | 123.8 (2) |
N1—C15—C16 | 123.30 (14) | C22—C21—H21 | 118.1 |
N1—C15—H15 | 118.3 | C25—C24—H24 | 120.1 |
C16—C15—H15 | 118.3 | C25—C24—C23 | 119.8 (2) |
O3—C13—C12 | 121.32 (14) | C23—C24—H24 | 120.1 |
O3—C13—C14 | 118.41 (14) | C24—C23—C26A | 104.0 (3) |
C12—C13—C14 | 120.27 (14) | C24—C23—C26Bii | 140.2 (3) |
C11—C12—H12 | 120.5 | C22—C23—C24 | 116.41 (19) |
C13—C12—C11 | 119.09 (14) | C22—C23—C26A | 139.6 (3) |
C13—C12—H12 | 120.5 | C22—C23—C26Bii | 103.4 (3) |
C9—C8—H8 | 117.0 | C26A—C23—C26Bii | 36.40 (16) |
C7—C8—C9 | 125.92 (15) | C21—C22—C23 | 120.0 (2) |
C7—C8—H8 | 117.0 | C21—C22—H22 | 120.0 |
C9—C14—H14 | 119.7 | C23—C22—H22 | 120.0 |
C13—C14—C9 | 120.51 (15) | C23—C26A—H26A | 122.0 |
C13—C14—H14 | 119.7 | C26Aiii—C26A—C23 | 116.1 (5) |
C5—C4—C7 | 123.95 (15) | C26Aiii—C26A—H26A | 122.0 |
C3—C4—C7 | 119.02 (15) | C23ii—C26B—H26B | 122.2 |
C3—C4—C5 | 117.02 (14) | C26Biv—C26B—H26B | 122.2 |
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. |
Crystal data top
2(C14H12O3)·3(C12H10N2)·C3H6O | Z = 2 |
Mr = 1061.21 | F(000) = 1120 |
Triclinic, P1 | Dx = 1.243 Mg m−3 |
a = 12.215 (3) Å | Mo Kα radiation, λ = 0.71073 Å |
b = 15.890 (4) Å | Cell parameters from 2202 reflections |
c = 17.769 (5) Å | θ = 2.3–22.3° |
α = 114.901 (6)° | µ = 0.08 mm−1 |
β = 92.443 (7)° | T = 220 K |
γ = 111.284 (6)° | Block, colourless |
V = 2835.8 (13) Å3 | 0.15 × 0.08 × 0.04 mm |
Data collection top
Bruker APEX-II CCD diffractometer | 5391 reflections with I > 2σ(I) |
φ and ω scans | Rint = 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 = 0.746 | h = −14→14 |
22595 measured reflections | k = −17→19 |
10635 independent reflections | l = −21→21 |
Refinement top
Refinement on F2 | Primary atom site location: dual |
Least-squares matrix: full | Hydrogen site location: mixed |
R[F2 > 2σ(F2)] = 0.062 | H 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 reflections | Δρmax = 0.71 e Å−3 |
765 parameters | Δρmin = −0.25 e Å−3 |
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 | x | y | z | Uiso*/Ueq | Occ. (<1) |
O2 | 0.19346 (19) | 0.62541 (15) | 0.19593 (13) | 0.0411 (5) | |
O5 | 0.68639 (19) | 1.13974 (16) | 0.20609 (14) | 0.0452 (6) | |
O1 | 0.4451 (2) | 0.13175 (18) | 0.38792 (15) | 0.0531 (6) | |
O3 | −0.1821 (2) | 0.35277 (17) | 0.15215 (15) | 0.0510 (6) | |
O6 | 0.3095 (2) | 0.85797 (18) | 0.14610 (17) | 0.0594 (7) | |
N3 | 0.5514 (2) | 0.1979 (2) | 0.12773 (17) | 0.0422 (6) | |
N5 | 0.2273 (2) | −0.05724 (19) | 1.06342 (17) | 0.0430 (6) | |
N6 | −0.0498 (2) | 0.30619 (19) | 0.86170 (16) | 0.0429 (6) | |
N4 | 0.2638 (2) | 0.5594 (2) | −0.06905 (17) | 0.0448 (7) | |
O4 | 1.0152 (2) | 0.7448 (2) | 0.4548 (2) | 0.0787 (9) | |
N2 | 0.8875 (3) | 0.5595 (2) | 0.43974 (18) | 0.0521 (7) | |
N1 | 0.6474 (2) | 0.0080 (2) | 0.55967 (19) | 0.0493 (7) | |
C25 | 0.1273 (3) | 0.5368 (2) | 0.19809 (16) | 0.0329 (7) | |
C28 | 0.0014 (3) | 0.3571 (2) | 0.20437 (17) | 0.0355 (7) | |
H28 | −0.042275 | 0.296392 | 0.206973 | 0.043* | |
C26 | 0.0033 (3) | 0.4921 (2) | 0.17459 (17) | 0.0352 (7) | |
H26 | −0.038389 | 0.522763 | 0.157344 | 0.042* | |
C23 | 0.1265 (3) | 0.4023 (2) | 0.22825 (17) | 0.0343 (7) | |
C13 | 0.6204 (3) | 1.0493 (2) | 0.20420 (17) | 0.0356 (7) | |
C24 | 0.1901 (3) | 0.4924 (2) | 0.22391 (17) | 0.0354 (7) | |
H24 | 0.275025 | 0.522869 | 0.238378 | 0.043* | |
C27 | −0.0593 (3) | 0.4011 (2) | 0.17670 (18) | 0.0372 (7) | |
C58 | 0.3947 (3) | 0.3258 (2) | 0.01060 (19) | 0.0363 (7) | |
H58 | 0.364228 | 0.286945 | −0.048758 | 0.044* | |
C48 | 0.0488 (3) | 0.2164 (2) | 0.93517 (18) | 0.0351 (7) | |
C60 | 0.3424 (2) | 0.4615 (2) | 0.00603 (19) | 0.0363 (7) | |
C4 | 0.8458 (3) | 0.8566 (2) | 0.33738 (18) | 0.0380 (7) | |
C59 | 0.3873 (3) | 0.4147 (2) | 0.04833 (19) | 0.0390 (7) | |
H59 | 0.413415 | 0.451338 | 0.108079 | 0.047* | |
C22 | 0.1964 (3) | 0.3591 (2) | 0.25644 (18) | 0.0377 (7) | |
H22 | 0.280020 | 0.388454 | 0.260855 | 0.045* | |
C43 | 0.1507 (3) | 0.0375 (2) | 0.98422 (18) | 0.0374 (7) | |
C14 | 0.6806 (3) | 1.0054 (2) | 0.23207 (17) | 0.0390 (7) | |
H14 | 0.765152 | 1.038134 | 0.251334 | 0.047* | |
C55 | 0.4460 (3) | 0.2827 (2) | 0.05285 (18) | 0.0345 (7) | |
C54 | 0.4992 (3) | 0.3333 (2) | 0.13970 (18) | 0.0403 (7) | |
H54 | 0.500260 | 0.397430 | 0.175105 | 0.048* | |
C18 | 0.2312 (3) | 0.2438 (2) | 0.30615 (18) | 0.0375 (7) | |
C9 | 0.6162 (3) | 0.9125 (2) | 0.23166 (17) | 0.0386 (7) | |
C12 | 0.4962 (3) | 1.0023 (2) | 0.17616 (18) | 0.0395 (7) | |
H12 | 0.455656 | 1.033157 | 0.158153 | 0.047* | |
C11 | 0.4312 (3) | 0.9090 (2) | 0.17463 (19) | 0.0415 (8) | |
C15 | 0.3723 (3) | 0.1654 (2) | 0.36219 (18) | 0.0403 (8) | |
C10 | 0.4913 (3) | 0.8653 (2) | 0.20281 (18) | 0.0416 (8) | |
H10 | 0.447230 | 0.802745 | 0.202477 | 0.050* | |
C21 | 0.1565 (3) | 0.2831 (2) | 0.27670 (18) | 0.0397 (7) | |
H21 | 0.072889 | 0.252043 | 0.271634 | 0.048* | |
C46 | 0.1080 (3) | 0.0843 (2) | 0.9400 (2) | 0.0409 (7) | |
H46 | 0.088152 | 0.049483 | 0.880099 | 0.049* | |
C49 | 0.0337 (3) | 0.3036 (2) | 0.98402 (19) | 0.0410 (8) | |
H49 | 0.057331 | 0.335111 | 1.043804 | 0.049* | |
C47 | 0.0952 (3) | 0.1699 (2) | 0.97686 (19) | 0.0371 (7) | |
H47 | 0.118450 | 0.205532 | 1.036740 | 0.045* | |
C53 | 0.5500 (3) | 0.2888 (2) | 0.1730 (2) | 0.0417 (8) | |
H53 | 0.586269 | 0.324705 | 0.231580 | 0.050* | |
C44 | 0.1616 (3) | −0.0534 (2) | 0.9376 (2) | 0.0415 (8) | |
H44 | 0.142988 | −0.084700 | 0.877657 | 0.050* | |
C17 | 0.3530 (3) | 0.2754 (3) | 0.3078 (2) | 0.0481 (8) | |
H17 | 0.389808 | 0.325070 | 0.290272 | 0.058* | |
C8 | 0.6749 (3) | 0.8628 (2) | 0.26157 (18) | 0.0427 (8) | |
H8 | 0.627007 | 0.795214 | 0.249879 | 0.051* | |
C56 | 0.4482 (3) | 0.1883 (2) | 0.0060 (2) | 0.0412 (8) | |
H56 | 0.413816 | 0.150715 | −0.052918 | 0.049* | |
C1 | 0.9594 (3) | 0.7782 (3) | 0.4142 (2) | 0.0487 (8) | |
C3 | 0.7899 (3) | 0.7572 (2) | 0.3239 (2) | 0.0456 (8) | |
H3A | 0.712055 | 0.715123 | 0.288148 | 0.055* | |
C2 | 0.8447 (3) | 0.7178 (3) | 0.3611 (2) | 0.0504 (9) | |
H2A | 0.804198 | 0.649661 | 0.350574 | 0.061* | |
C41 | 0.2177 (3) | 0.0299 (2) | 1.1082 (2) | 0.0438 (8) | |
H41 | 0.237403 | 0.059411 | 1.167962 | 0.053* | |
C57 | 0.5000 (3) | 0.1495 (2) | 0.0452 (2) | 0.0439 (8) | |
H57 | 0.499054 | 0.084946 | 0.011691 | 0.053* | |
C36 | 0.7069 (3) | 0.1756 (2) | 0.5296 (2) | 0.0454 (8) | |
C45 | 0.1992 (3) | −0.0972 (2) | 0.9787 (2) | 0.0446 (8) | |
H45 | 0.205737 | −0.158748 | 0.945577 | 0.053* | |
C51 | −0.0317 (3) | 0.2232 (2) | 0.8140 (2) | 0.0465 (8) | |
H51 | −0.052532 | 0.195282 | 0.754368 | 0.056* | |
C50 | −0.0156 (3) | 0.3444 (2) | 0.9459 (2) | 0.0450 (8) | |
H50 | −0.026054 | 0.403275 | 0.981169 | 0.054* | |
C61 | 0.3383 (3) | 0.5547 (2) | 0.0540 (2) | 0.0415 (8) | |
H61 | 0.362094 | 0.586775 | 0.113800 | 0.050* | |
C64 | 0.3054 (3) | 0.4189 (2) | −0.0817 (2) | 0.0439 (8) | |
H64 | 0.306313 | 0.355795 | −0.117604 | 0.053* | |
C5 | 0.9614 (3) | 0.9148 (2) | 0.3891 (2) | 0.0474 (8) | |
H5A | 1.002761 | 0.982369 | 0.398535 | 0.057* | |
C52 | 0.0153 (3) | 0.1769 (2) | 0.84724 (19) | 0.0455 (8) | |
H52 | 0.025060 | 0.118153 | 0.810633 | 0.055* | |
O7 | 0.5154 (3) | 0.5483 (2) | 0.2963 (2) | 0.1097 (12) | |
C6 | 1.0177 (3) | 0.8767 (3) | 0.4271 (2) | 0.0497 (9) | |
H6A | 1.096212 | 0.918274 | 0.461839 | 0.060* | |
C62 | 0.2996 (3) | 0.6005 (2) | 0.0149 (2) | 0.0455 (8) | |
H62 | 0.298515 | 0.664078 | 0.049186 | 0.055* | |
C42 | 0.1811 (3) | 0.0795 (2) | 1.0727 (2) | 0.0433 (8) | |
H42 | 0.176327 | 0.141333 | 1.107679 | 0.052* | |
C40 | 0.6636 (3) | 0.0778 (3) | 0.4630 (2) | 0.0483 (8) | |
H40 | 0.653341 | 0.066395 | 0.406240 | 0.058* | |
C39 | 0.6354 (3) | −0.0030 (2) | 0.4808 (2) | 0.0484 (8) | |
H39 | 0.606230 | −0.069372 | 0.434793 | 0.058* | |
C7 | 0.7880 (3) | 0.9032 (2) | 0.30312 (19) | 0.0445 (8) | |
H7 | 0.836902 | 0.969219 | 0.311703 | 0.053* | |
C16 | 0.4228 (3) | 0.2369 (2) | 0.3344 (2) | 0.0485 (8) | |
H16 | 0.505107 | 0.259544 | 0.333572 | 0.058* | |
C38 | 0.6871 (3) | 0.1021 (3) | 0.6225 (2) | 0.0533 (9) | |
H38 | 0.694632 | 0.111544 | 0.678647 | 0.064* | |
C19 | 0.1809 (3) | 0.1717 (3) | 0.3337 (2) | 0.0504 (9) | |
H19 | 0.098306 | 0.148342 | 0.333577 | 0.061* | |
C63 | 0.2675 (3) | 0.4689 (2) | −0.1157 (2) | 0.0493 (9) | |
H63 | 0.242612 | 0.438294 | −0.175376 | 0.059* | |
C33 | 0.8444 (3) | 0.4668 (3) | 0.3734 (2) | 0.0540 (9) | |
H33 | 0.845025 | 0.461368 | 0.318718 | 0.065* | |
C31 | 0.7937 (3) | 0.3824 (3) | 0.4573 (3) | 0.0566 (9) | |
C37 | 0.7179 (3) | 0.1861 (3) | 0.6110 (2) | 0.0550 (9) | |
H37 | 0.746638 | 0.251400 | 0.658417 | 0.066* | |
C20 | 0.2503 (3) | 0.1331 (3) | 0.3617 (2) | 0.0525 (9) | |
H20 | 0.214027 | 0.084558 | 0.380393 | 0.063* | |
C32 | 0.7995 (3) | 0.3791 (3) | 0.3801 (2) | 0.0575 (9) | |
H32 | 0.772214 | 0.315568 | 0.330811 | 0.069* | |
C30 | 0.8383 (4) | 0.4800 (3) | 0.5278 (2) | 0.0692 (12) | |
H30 | 0.837598 | 0.487329 | 0.583065 | 0.083* | |
C35 | 0.7486 (4) | 0.2716 (4) | 0.5263 (3) | 0.0415 (11) | 0.75 |
H35 | 0.781887 | 0.331750 | 0.578735 | 0.050* | 0.75 |
C29 | 0.8825 (4) | 0.5638 (3) | 0.5158 (2) | 0.0646 (11) | |
H29 | 0.911294 | 0.628544 | 0.563893 | 0.078* | |
C34 | 0.7443 (4) | 0.2828 (4) | 0.4564 (3) | 0.0413 (10) | 0.75 |
H34 | 0.707628 | 0.223666 | 0.403442 | 0.050* | 0.75 |
C65 | 0.5320 (4) | 0.6018 (3) | 0.3707 (3) | 0.0802 (13) | |
C67 | 0.5210 (5) | 0.7002 (4) | 0.4042 (3) | 0.1053 (17) | |
H67A | 0.600539 | 0.756257 | 0.431887 | 0.158* | |
H67B | 0.470582 | 0.703535 | 0.445112 | 0.158* | |
H67C | 0.484793 | 0.705273 | 0.357519 | 0.158* | |
C66 | 0.5739 (7) | 0.5764 (4) | 0.4359 (4) | 0.143 (2) | |
H66A | 0.508319 | 0.554899 | 0.462026 | 0.215* | |
H66B | 0.641522 | 0.636305 | 0.479376 | 0.215* | |
H66C | 0.598967 | 0.521478 | 0.408314 | 0.215* | |
C0AA | 0.7818 (13) | 0.3225 (9) | 0.5214 (10) | 0.048 (4) | 0.25 |
H0AA | 0.816505 | 0.352621 | 0.579844 | 0.058* | 0.25 |
C1AA | 0.7164 (14) | 0.2303 (10) | 0.4715 (11) | 0.053 (4) | 0.25 |
H1AA | 0.681076 | 0.200277 | 0.413207 | 0.064* | 0.25 |
H2 | 0.144 (3) | 0.645 (3) | 0.181 (2) | 0.063 (11)* | |
H3 | −0.206 (4) | 0.379 (3) | 0.126 (2) | 0.082 (14)* | |
H6 | 0.282 (4) | 0.884 (3) | 0.118 (2) | 0.093 (15)* | |
H1 | 0.410 (4) | 0.091 (3) | 0.409 (3) | 0.105 (17)* | |
H5 | 0.645 (3) | 1.159 (3) | 0.182 (2) | 0.079 (13)* | |
H4 | 0.970 (4) | 0.686 (3) | 0.452 (4) | 0.16 (3)* | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
O2 | 0.0415 (13) | 0.0365 (12) | 0.0490 (13) | 0.0162 (10) | 0.0052 (10) | 0.0239 (11) |
O5 | 0.0451 (14) | 0.0394 (13) | 0.0536 (13) | 0.0185 (11) | 0.0002 (10) | 0.0241 (11) |
O1 | 0.0485 (15) | 0.0639 (16) | 0.0739 (16) | 0.0293 (13) | 0.0115 (12) | 0.0511 (14) |
O3 | 0.0389 (14) | 0.0569 (15) | 0.0742 (16) | 0.0222 (12) | 0.0094 (11) | 0.0440 (14) |
O6 | 0.0377 (14) | 0.0602 (15) | 0.0950 (19) | 0.0146 (12) | 0.0007 (12) | 0.0554 (15) |
N3 | 0.0407 (16) | 0.0451 (16) | 0.0542 (17) | 0.0201 (13) | 0.0131 (13) | 0.0330 (14) |
N5 | 0.0391 (16) | 0.0421 (16) | 0.0526 (16) | 0.0191 (13) | 0.0047 (12) | 0.0253 (14) |
N6 | 0.0458 (16) | 0.0439 (16) | 0.0501 (16) | 0.0214 (13) | 0.0103 (12) | 0.0297 (14) |
N4 | 0.0398 (16) | 0.0449 (16) | 0.0586 (18) | 0.0199 (13) | 0.0076 (13) | 0.0305 (15) |
O4 | 0.0489 (16) | 0.080 (2) | 0.134 (3) | 0.0219 (15) | −0.0052 (15) | 0.080 (2) |
N2 | 0.063 (2) | 0.0489 (18) | 0.0584 (18) | 0.0265 (15) | 0.0129 (15) | 0.0346 (16) |
N1 | 0.0499 (18) | 0.0533 (18) | 0.0624 (19) | 0.0241 (15) | 0.0153 (14) | 0.0403 (17) |
C25 | 0.0418 (18) | 0.0300 (16) | 0.0278 (14) | 0.0180 (14) | 0.0043 (12) | 0.0122 (13) |
C28 | 0.0411 (18) | 0.0350 (17) | 0.0373 (16) | 0.0194 (14) | 0.0072 (13) | 0.0202 (14) |
C26 | 0.0437 (19) | 0.0348 (17) | 0.0347 (15) | 0.0228 (15) | 0.0058 (13) | 0.0177 (14) |
C23 | 0.0432 (18) | 0.0365 (17) | 0.0276 (14) | 0.0230 (15) | 0.0046 (13) | 0.0139 (13) |
C13 | 0.0461 (19) | 0.0341 (17) | 0.0297 (15) | 0.0216 (15) | 0.0082 (13) | 0.0137 (13) |
C24 | 0.0350 (17) | 0.0367 (17) | 0.0360 (16) | 0.0170 (14) | 0.0021 (13) | 0.0172 (14) |
C27 | 0.0349 (18) | 0.0424 (18) | 0.0395 (16) | 0.0207 (15) | 0.0076 (13) | 0.0201 (15) |
C58 | 0.0363 (17) | 0.0365 (17) | 0.0391 (16) | 0.0161 (14) | 0.0075 (13) | 0.0197 (15) |
C48 | 0.0360 (17) | 0.0363 (17) | 0.0415 (17) | 0.0170 (14) | 0.0111 (13) | 0.0239 (15) |
C60 | 0.0304 (16) | 0.0379 (18) | 0.0465 (18) | 0.0156 (14) | 0.0123 (13) | 0.0237 (15) |
C4 | 0.0408 (18) | 0.0462 (19) | 0.0419 (17) | 0.0271 (16) | 0.0139 (14) | 0.0256 (15) |
C59 | 0.0412 (18) | 0.0426 (18) | 0.0421 (17) | 0.0206 (15) | 0.0110 (14) | 0.0249 (15) |
C22 | 0.0397 (18) | 0.0385 (17) | 0.0400 (16) | 0.0193 (15) | 0.0049 (13) | 0.0207 (15) |
C43 | 0.0362 (17) | 0.0398 (18) | 0.0439 (17) | 0.0182 (14) | 0.0082 (13) | 0.0244 (15) |
C14 | 0.0401 (18) | 0.0473 (19) | 0.0355 (16) | 0.0249 (16) | 0.0036 (13) | 0.0195 (15) |
C55 | 0.0355 (17) | 0.0364 (17) | 0.0417 (17) | 0.0175 (14) | 0.0145 (13) | 0.0245 (15) |
C54 | 0.0464 (19) | 0.0393 (17) | 0.0391 (17) | 0.0223 (15) | 0.0107 (14) | 0.0180 (15) |
C18 | 0.0445 (19) | 0.0391 (17) | 0.0405 (16) | 0.0216 (15) | 0.0107 (14) | 0.0252 (15) |
C9 | 0.051 (2) | 0.0452 (19) | 0.0287 (15) | 0.0302 (16) | 0.0090 (13) | 0.0168 (14) |
C12 | 0.0441 (19) | 0.0454 (19) | 0.0398 (17) | 0.0264 (16) | 0.0065 (14) | 0.0233 (15) |
C11 | 0.0439 (19) | 0.0434 (19) | 0.0438 (18) | 0.0218 (16) | 0.0054 (14) | 0.0236 (16) |
C15 | 0.046 (2) | 0.0424 (18) | 0.0425 (17) | 0.0217 (16) | 0.0048 (14) | 0.0267 (15) |
C10 | 0.049 (2) | 0.0432 (18) | 0.0470 (18) | 0.0254 (16) | 0.0087 (15) | 0.0288 (16) |
C21 | 0.0454 (19) | 0.0434 (18) | 0.0370 (16) | 0.0242 (15) | 0.0070 (13) | 0.0202 (15) |
C46 | 0.0455 (19) | 0.0411 (18) | 0.0420 (17) | 0.0201 (15) | 0.0093 (14) | 0.0232 (15) |
C49 | 0.051 (2) | 0.0396 (18) | 0.0378 (16) | 0.0233 (16) | 0.0084 (14) | 0.0192 (15) |
C47 | 0.0378 (18) | 0.0412 (18) | 0.0402 (17) | 0.0191 (15) | 0.0091 (13) | 0.0238 (15) |
C53 | 0.0433 (19) | 0.0457 (19) | 0.0423 (17) | 0.0206 (16) | 0.0074 (14) | 0.0245 (16) |
C44 | 0.0452 (19) | 0.0361 (17) | 0.0454 (18) | 0.0203 (15) | 0.0057 (14) | 0.0187 (15) |
C17 | 0.046 (2) | 0.058 (2) | 0.064 (2) | 0.0261 (17) | 0.0165 (16) | 0.0453 (19) |
C8 | 0.051 (2) | 0.0459 (19) | 0.0432 (17) | 0.0262 (16) | 0.0072 (15) | 0.0269 (16) |
C56 | 0.0437 (19) | 0.0380 (18) | 0.0433 (17) | 0.0176 (15) | 0.0098 (14) | 0.0200 (15) |
C1 | 0.0398 (19) | 0.059 (2) | 0.068 (2) | 0.0252 (17) | 0.0068 (16) | 0.0438 (19) |
C3 | 0.0368 (18) | 0.049 (2) | 0.056 (2) | 0.0205 (16) | 0.0052 (15) | 0.0280 (17) |
C2 | 0.0377 (19) | 0.050 (2) | 0.072 (2) | 0.0160 (16) | 0.0018 (16) | 0.0388 (19) |
C41 | 0.0442 (19) | 0.0441 (19) | 0.0434 (18) | 0.0195 (16) | 0.0015 (14) | 0.0207 (16) |
C57 | 0.049 (2) | 0.0381 (18) | 0.051 (2) | 0.0232 (16) | 0.0081 (16) | 0.0233 (16) |
C36 | 0.046 (2) | 0.0418 (17) | 0.064 (2) | 0.0235 (16) | 0.0163 (16) | 0.0339 (17) |
C45 | 0.045 (2) | 0.0361 (18) | 0.056 (2) | 0.0212 (15) | 0.0085 (15) | 0.0214 (16) |
C51 | 0.059 (2) | 0.049 (2) | 0.0417 (18) | 0.0290 (18) | 0.0105 (15) | 0.0243 (17) |
C50 | 0.057 (2) | 0.0412 (19) | 0.0490 (19) | 0.0296 (17) | 0.0158 (16) | 0.0245 (16) |
C61 | 0.0429 (19) | 0.0438 (19) | 0.0460 (18) | 0.0236 (15) | 0.0112 (14) | 0.0235 (16) |
C64 | 0.049 (2) | 0.0389 (18) | 0.0489 (19) | 0.0233 (16) | 0.0083 (15) | 0.0215 (16) |
C5 | 0.044 (2) | 0.0428 (19) | 0.063 (2) | 0.0190 (16) | 0.0089 (16) | 0.0317 (17) |
C52 | 0.064 (2) | 0.0416 (18) | 0.0428 (18) | 0.0346 (17) | 0.0148 (16) | 0.0197 (16) |
O7 | 0.111 (3) | 0.076 (2) | 0.077 (2) | 0.0283 (19) | 0.0119 (19) | −0.0098 (18) |
C6 | 0.0386 (19) | 0.054 (2) | 0.067 (2) | 0.0201 (17) | 0.0026 (16) | 0.0375 (19) |
C62 | 0.0425 (19) | 0.0400 (18) | 0.061 (2) | 0.0213 (15) | 0.0134 (16) | 0.0261 (17) |
C42 | 0.051 (2) | 0.0421 (18) | 0.0466 (18) | 0.0272 (16) | 0.0093 (15) | 0.0225 (16) |
C40 | 0.052 (2) | 0.062 (2) | 0.0442 (19) | 0.0278 (18) | 0.0145 (15) | 0.0328 (18) |
C39 | 0.050 (2) | 0.0410 (19) | 0.051 (2) | 0.0202 (16) | 0.0070 (16) | 0.0181 (17) |
C7 | 0.047 (2) | 0.052 (2) | 0.0511 (19) | 0.0277 (17) | 0.0143 (16) | 0.0322 (17) |
C16 | 0.0401 (19) | 0.058 (2) | 0.067 (2) | 0.0225 (17) | 0.0127 (16) | 0.0452 (19) |
C38 | 0.050 (2) | 0.074 (3) | 0.0418 (19) | 0.024 (2) | 0.0084 (16) | 0.034 (2) |
C19 | 0.040 (2) | 0.062 (2) | 0.070 (2) | 0.0235 (17) | 0.0133 (16) | 0.047 (2) |
C63 | 0.058 (2) | 0.047 (2) | 0.0447 (19) | 0.0252 (17) | 0.0041 (16) | 0.0221 (17) |
C33 | 0.066 (2) | 0.065 (3) | 0.0430 (19) | 0.031 (2) | 0.0107 (17) | 0.032 (2) |
C31 | 0.058 (2) | 0.054 (2) | 0.087 (3) | 0.0360 (18) | 0.032 (2) | 0.047 (2) |
C37 | 0.067 (2) | 0.044 (2) | 0.046 (2) | 0.0229 (18) | 0.0107 (17) | 0.0148 (17) |
C20 | 0.043 (2) | 0.058 (2) | 0.078 (2) | 0.0205 (17) | 0.0151 (17) | 0.051 (2) |
C32 | 0.062 (2) | 0.046 (2) | 0.060 (2) | 0.0242 (18) | 0.0091 (18) | 0.0190 (19) |
C30 | 0.110 (4) | 0.091 (3) | 0.051 (2) | 0.064 (3) | 0.040 (2) | 0.052 (2) |
C35 | 0.043 (3) | 0.031 (2) | 0.047 (3) | 0.011 (2) | 0.009 (2) | 0.019 (2) |
C29 | 0.099 (3) | 0.053 (2) | 0.049 (2) | 0.041 (2) | 0.017 (2) | 0.0227 (19) |
C34 | 0.044 (3) | 0.0375 (19) | 0.041 (2) | 0.016 (2) | 0.007 (2) | 0.018 (2) |
C65 | 0.062 (3) | 0.059 (3) | 0.086 (3) | 0.014 (2) | 0.019 (2) | 0.016 (3) |
C67 | 0.105 (4) | 0.103 (4) | 0.094 (4) | 0.065 (3) | 0.027 (3) | 0.015 (3) |
C66 | 0.204 (7) | 0.108 (4) | 0.135 (5) | 0.067 (5) | 0.059 (5) | 0.068 (4) |
C0AA | 0.043 (5) | 0.054 (5) | 0.041 (5) | 0.021 (4) | 0.011 (4) | 0.015 (4) |
C1AA | 0.055 (6) | 0.054 (6) | 0.047 (5) | 0.022 (4) | 0.013 (4) | 0.022 (4) |
Geometric parameters (Å, º) top
O2—C25 | 1.364 (3) | C49—C50 | 1.364 (4) |
O2—H2 | 0.861 (18) | C47—H47 | 0.9400 |
O5—C13 | 1.353 (4) | C53—H53 | 0.9400 |
O5—H5 | 0.857 (18) | C44—H44 | 0.9400 |
O1—C15 | 1.342 (3) | C44—C45 | 1.365 (4) |
O1—H1 | 0.878 (19) | C17—H17 | 0.9400 |
O3—C27 | 1.363 (4) | C17—C16 | 1.384 (4) |
O3—H3 | 0.841 (18) | C8—H8 | 0.9400 |
O6—C11 | 1.356 (4) | C8—C7 | 1.317 (4) |
O6—H6 | 0.877 (18) | C56—H56 | 0.9400 |
N3—C53 | 1.331 (4) | C56—C57 | 1.367 (4) |
N3—C57 | 1.326 (4) | C1—C2 | 1.387 (4) |
N5—C41 | 1.328 (4) | C1—C6 | 1.373 (4) |
N5—C45 | 1.335 (4) | C3—H3A | 0.9400 |
N6—C51 | 1.339 (4) | C3—C2 | 1.376 (4) |
N6—C50 | 1.333 (4) | C2—H2A | 0.9400 |
N4—C62 | 1.326 (4) | C41—H41 | 0.9400 |
N4—C63 | 1.344 (4) | C41—C42 | 1.367 (4) |
O4—C1 | 1.345 (4) | C57—H57 | 0.9400 |
O4—H4 | 0.87 (2) | C36—C40 | 1.377 (4) |
N2—C33 | 1.326 (4) | C36—C37 | 1.380 (5) |
N2—C29 | 1.329 (4) | C36—C35 | 1.449 (5) |
N1—C39 | 1.333 (4) | C36—C1AA | 1.588 (18) |
N1—C38 | 1.319 (4) | C45—H45 | 0.9400 |
C25—C26 | 1.374 (4) | C51—H51 | 0.9400 |
C25—C24 | 1.390 (4) | C51—C52 | 1.366 (4) |
C28—H28 | 0.9400 | C50—H50 | 0.9400 |
C28—C23 | 1.386 (4) | C61—H61 | 0.9400 |
C28—C27 | 1.384 (4) | C61—C62 | 1.374 (4) |
C26—H26 | 0.9400 | C64—H64 | 0.9400 |
C26—C27 | 1.386 (4) | C64—C63 | 1.363 (4) |
C23—C24 | 1.396 (4) | C5—H5A | 0.9400 |
C23—C22 | 1.460 (4) | C5—C6 | 1.379 (4) |
C13—C14 | 1.381 (4) | C52—H52 | 0.9400 |
C13—C12 | 1.381 (4) | O7—C65 | 1.189 (5) |
C24—H24 | 0.9400 | C6—H6A | 0.9400 |
C58—H58 | 0.9400 | C62—H62 | 0.9400 |
C58—C59 | 1.324 (4) | C42—H42 | 0.9400 |
C58—C55 | 1.459 (4) | C40—H40 | 0.9400 |
C48—C49 | 1.377 (4) | C40—C39 | 1.377 (4) |
C48—C47 | 1.463 (4) | C39—H39 | 0.9400 |
C48—C52 | 1.391 (4) | C7—H7 | 0.9400 |
C60—C59 | 1.467 (4) | C16—H16 | 0.9400 |
C60—C61 | 1.384 (4) | C38—H38 | 0.9400 |
C60—C64 | 1.387 (4) | C38—C37 | 1.355 (4) |
C4—C3 | 1.379 (4) | C19—H19 | 0.9400 |
C4—C5 | 1.385 (4) | C19—C20 | 1.392 (4) |
C4—C7 | 1.463 (4) | C63—H63 | 0.9400 |
C59—H59 | 0.9400 | C33—H33 | 0.9400 |
C22—H22 | 0.9400 | C33—C32 | 1.359 (5) |
C22—C21 | 1.333 (4) | C31—C32 | 1.355 (5) |
C43—C46 | 1.476 (4) | C31—C30 | 1.402 (5) |
C43—C44 | 1.390 (4) | C31—C34 | 1.467 (6) |
C43—C42 | 1.394 (4) | C31—C0AA | 1.746 (16) |
C14—H14 | 0.9400 | C37—H37 | 0.9400 |
C14—C9 | 1.395 (4) | C20—H20 | 0.9400 |
C55—C54 | 1.393 (4) | C32—H32 | 0.9400 |
C55—C56 | 1.387 (4) | C30—H30 | 0.9400 |
C54—H54 | 0.9400 | C30—C29 | 1.356 (5) |
C54—C53 | 1.369 (4) | C35—H35 | 0.9400 |
C18—C21 | 1.465 (4) | C35—C34 | 1.328 (5) |
C18—C17 | 1.380 (4) | C29—H29 | 0.9400 |
C18—C19 | 1.384 (4) | C34—H34 | 0.9400 |
C9—C10 | 1.389 (4) | C65—C67 | 1.480 (6) |
C9—C8 | 1.468 (4) | C65—C66 | 1.505 (7) |
C12—H12 | 0.9400 | C67—H67A | 0.9700 |
C12—C11 | 1.393 (4) | C67—H67B | 0.9700 |
C11—C10 | 1.380 (4) | C67—H67C | 0.9700 |
C15—C16 | 1.380 (4) | C66—H66A | 0.9700 |
C15—C20 | 1.386 (4) | C66—H66B | 0.9700 |
C10—H10 | 0.9400 | C66—H66C | 0.9700 |
C21—H21 | 0.9400 | C0AA—H0AA | 0.9400 |
C46—H46 | 0.9400 | C0AA—C1AA | 1.253 (14) |
C46—C47 | 1.311 (4) | C1AA—H1AA | 0.9400 |
C49—H49 | 0.9400 | | |
| | | |
C25—O2—H2 | 108 (2) | C3—C2—C1 | 120.2 (3) |
C13—O5—H5 | 113 (3) | C3—C2—H2A | 119.9 |
C15—O1—H1 | 114 (3) | N5—C41—H41 | 117.9 |
C27—O3—H3 | 108 (3) | N5—C41—C42 | 124.1 (3) |
C11—O6—H6 | 110 (3) | C42—C41—H41 | 117.9 |
C57—N3—C53 | 116.3 (3) | N3—C57—C56 | 123.7 (3) |
C41—N5—C45 | 116.7 (3) | N3—C57—H57 | 118.2 |
C50—N6—C51 | 115.8 (3) | C56—C57—H57 | 118.2 |
C62—N4—C63 | 116.5 (3) | C40—C36—C37 | 117.1 (3) |
C1—O4—H4 | 115 (4) | C40—C36—C35 | 128.5 (3) |
C33—N2—C29 | 116.3 (3) | C40—C36—C1AA | 95.7 (6) |
C38—N1—C39 | 116.5 (3) | C37—C36—C35 | 114.3 (3) |
O2—C25—C26 | 121.4 (2) | C37—C36—C1AA | 147.1 (6) |
O2—C25—C24 | 117.5 (3) | N5—C45—C44 | 123.4 (3) |
C26—C25—C24 | 121.1 (3) | N5—C45—H45 | 118.3 |
C23—C28—H28 | 119.9 | C44—C45—H45 | 118.3 |
C27—C28—H28 | 119.9 | N6—C51—H51 | 118.2 |
C27—C28—C23 | 120.2 (3) | N6—C51—C52 | 123.6 (3) |
C25—C26—H26 | 120.5 | C52—C51—H51 | 118.2 |
C25—C26—C27 | 119.0 (3) | N6—C50—C49 | 124.1 (3) |
C27—C26—H26 | 120.5 | N6—C50—H50 | 117.9 |
C28—C23—C24 | 119.2 (3) | C49—C50—H50 | 117.9 |
C28—C23—C22 | 123.1 (3) | C60—C61—H61 | 119.7 |
C24—C23—C22 | 117.7 (3) | C62—C61—C60 | 120.5 (3) |
O5—C13—C14 | 118.1 (3) | C62—C61—H61 | 119.7 |
O5—C13—C12 | 121.4 (3) | C60—C64—H64 | 120.1 |
C12—C13—C14 | 120.5 (3) | C63—C64—C60 | 119.8 (3) |
C25—C24—C23 | 119.7 (3) | C63—C64—H64 | 120.1 |
C25—C24—H24 | 120.2 | C4—C5—H5A | 119.0 |
C23—C24—H24 | 120.2 | C6—C5—C4 | 122.1 (3) |
O3—C27—C28 | 118.1 (3) | C6—C5—H5A | 119.0 |
O3—C27—C26 | 121.1 (3) | C48—C52—H52 | 119.9 |
C28—C27—C26 | 120.8 (3) | C51—C52—C48 | 120.1 (3) |
C59—C58—H58 | 117.1 | C51—C52—H52 | 119.9 |
C59—C58—C55 | 125.9 (3) | C1—C6—C5 | 120.1 (3) |
C55—C58—H58 | 117.1 | C1—C6—H6A | 119.9 |
C49—C48—C47 | 119.7 (3) | C5—C6—H6A | 119.9 |
C49—C48—C52 | 116.1 (3) | N4—C62—C61 | 123.1 (3) |
C52—C48—C47 | 124.2 (3) | N4—C62—H62 | 118.4 |
C61—C60—C59 | 120.1 (3) | C61—C62—H62 | 118.4 |
C61—C60—C64 | 116.2 (3) | C43—C42—H42 | 120.4 |
C64—C60—C59 | 123.7 (3) | C41—C42—C43 | 119.3 (3) |
C3—C4—C5 | 116.8 (3) | C41—C42—H42 | 120.4 |
C3—C4—C7 | 123.6 (3) | C36—C40—H40 | 120.5 |
C5—C4—C7 | 119.6 (3) | C36—C40—C39 | 119.0 (3) |
C58—C59—C60 | 126.4 (3) | C39—C40—H40 | 120.5 |
C58—C59—H59 | 116.8 | N1—C39—C40 | 123.5 (3) |
C60—C59—H59 | 116.8 | N1—C39—H39 | 118.3 |
C23—C22—H22 | 115.9 | C40—C39—H39 | 118.3 |
C21—C22—C23 | 128.1 (3) | C4—C7—H7 | 116.4 |
C21—C22—H22 | 115.9 | C8—C7—C4 | 127.1 (3) |
C44—C43—C46 | 120.2 (3) | C8—C7—H7 | 116.4 |
C44—C43—C42 | 116.5 (3) | C15—C16—C17 | 120.3 (3) |
C42—C43—C46 | 123.3 (3) | C15—C16—H16 | 119.8 |
C13—C14—H14 | 120.0 | C17—C16—H16 | 119.8 |
C13—C14—C9 | 120.0 (3) | N1—C38—H38 | 118.0 |
C9—C14—H14 | 120.0 | N1—C38—C37 | 124.0 (3) |
C54—C55—C58 | 123.5 (3) | C37—C38—H38 | 118.0 |
C56—C55—C58 | 120.4 (3) | C18—C19—H19 | 119.3 |
C56—C55—C54 | 116.1 (3) | C18—C19—C20 | 121.3 (3) |
C55—C54—H54 | 120.4 | C20—C19—H19 | 119.3 |
C53—C54—C55 | 119.3 (3) | N4—C63—C64 | 123.9 (3) |
C53—C54—H54 | 120.4 | N4—C63—H63 | 118.1 |
C17—C18—C21 | 122.7 (3) | C64—C63—H63 | 118.1 |
C17—C18—C19 | 116.9 (3) | N2—C33—H33 | 118.1 |
C19—C18—C21 | 120.5 (3) | N2—C33—C32 | 123.7 (3) |
C14—C9—C8 | 122.6 (3) | C32—C33—H33 | 118.1 |
C10—C9—C14 | 119.1 (3) | C32—C31—C30 | 116.2 (3) |
C10—C9—C8 | 118.4 (3) | C32—C31—C34 | 115.6 (4) |
C13—C12—H12 | 120.1 | C32—C31—C0AA | 149.4 (5) |
C13—C12—C11 | 119.9 (3) | C30—C31—C34 | 128.2 (4) |
C11—C12—H12 | 120.1 | C30—C31—C0AA | 92.8 (5) |
O6—C11—C12 | 122.6 (3) | C36—C37—H37 | 120.1 |
O6—C11—C10 | 117.8 (3) | C38—C37—C36 | 119.9 (3) |
C10—C11—C12 | 119.6 (3) | C38—C37—H37 | 120.1 |
O1—C15—C16 | 117.5 (3) | C15—C20—C19 | 120.9 (3) |
O1—C15—C20 | 124.4 (3) | C15—C20—H20 | 119.6 |
C16—C15—C20 | 118.1 (3) | C19—C20—H20 | 119.6 |
C9—C10—H10 | 119.6 | C33—C32—H32 | 119.7 |
C11—C10—C9 | 120.9 (3) | C31—C32—C33 | 120.6 (3) |
C11—C10—H10 | 119.6 | C31—C32—H32 | 119.7 |
C22—C21—C18 | 125.9 (3) | C31—C30—H30 | 120.2 |
C22—C21—H21 | 117.1 | C29—C30—C31 | 119.6 (3) |
C18—C21—H21 | 117.1 | C29—C30—H30 | 120.2 |
C43—C46—H46 | 117.1 | C36—C35—H35 | 116.8 |
C47—C46—C43 | 125.9 (3) | C34—C35—C36 | 126.4 (5) |
C47—C46—H46 | 117.1 | C34—C35—H35 | 116.8 |
C48—C49—H49 | 119.9 | N2—C29—C30 | 123.6 (3) |
C50—C49—C48 | 120.2 (3) | N2—C29—H29 | 118.2 |
C50—C49—H49 | 119.9 | C30—C29—H29 | 118.2 |
C48—C47—H47 | 116.4 | C31—C34—H34 | 118.2 |
C46—C47—C48 | 127.3 (3) | C35—C34—C31 | 123.7 (5) |
C46—C47—H47 | 116.4 | C35—C34—H34 | 118.2 |
N3—C53—C54 | 124.3 (3) | O7—C65—C67 | 122.0 (5) |
N3—C53—H53 | 117.8 | O7—C65—C66 | 121.5 (5) |
C54—C53—H53 | 117.8 | C67—C65—C66 | 116.4 (4) |
C43—C44—H44 | 120.0 | C65—C67—H67A | 109.5 |
C45—C44—C43 | 120.1 (3) | C65—C67—H67B | 109.5 |
C45—C44—H44 | 120.0 | C65—C67—H67C | 109.5 |
C18—C17—H17 | 118.7 | H67A—C67—H67B | 109.5 |
C18—C17—C16 | 122.5 (3) | H67A—C67—H67C | 109.5 |
C16—C17—H17 | 118.7 | H67B—C67—H67C | 109.5 |
C9—C8—H8 | 116.7 | C65—C66—H66A | 109.5 |
C7—C8—C9 | 126.6 (3) | C65—C66—H66B | 109.5 |
C7—C8—H8 | 116.7 | C65—C66—H66C | 109.5 |
C55—C56—H56 | 119.8 | H66A—C66—H66B | 109.5 |
C57—C56—C55 | 120.3 (3) | H66A—C66—H66C | 109.5 |
C57—C56—H56 | 119.8 | H66B—C66—H66C | 109.5 |
O4—C1—C2 | 122.6 (3) | C31—C0AA—H0AA | 128.0 |
O4—C1—C6 | 118.6 (3) | C1AA—C0AA—C31 | 104.0 (14) |
C6—C1—C2 | 118.8 (3) | C1AA—C0AA—H0AA | 128.0 |
C4—C3—H3A | 119.0 | C36—C1AA—H1AA | 128.0 |
C2—C3—C4 | 122.0 (3) | C0AA—C1AA—C36 | 104.0 (15) |
C2—C3—H3A | 119.0 | C0AA—C1AA—H1AA | 128.0 |
C1—C2—H2A | 119.9 | | |
Hydrogen-bond geometry (Å, º) top
D—H···A | D—H | H···A | D···A | D—H···A |
O2—H2···N6i | 0.86 (2) | 1.88 (2) | 2.735 (3) | 172 (3) |
O3—H3···N4ii | 0.84 (2) | 1.94 (2) | 2.782 (3) | 177 (4) |
O6—H6···N5iii | 0.88 (2) | 1.86 (2) | 2.739 (3) | 178 (4) |
O1—H1···N1iv | 0.88 (2) | 1.79 (2) | 2.661 (3) | 169 (4) |
O5—H5···N3v | 0.86 (2) | 1.88 (2) | 2.740 (3) | 179 (4) |
O4—H4···N2 | 0.87 (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, z−1; (iv) −x+1, −y, −z+1; (v) x, y+1, z. |
Crystal data top
C14H12O3·1.5(C12H10N2)·CH4O | Z = 2 |
Mr = 533.61 | F(000) = 564 |
Triclinic, P1 | Dx = 1.266 Mg m−3 |
a = 11.765 (3) Å | Mo Kα radiation, λ = 0.71073 Å |
b = 11.892 (3) Å | Cell parameters from 1641 reflections |
c = 12.314 (3) Å | θ = 2.3–21.7° |
α = 95.213 (7)° | µ = 0.08 mm−1 |
β = 111.706 (6)° | T = 220 K |
γ = 114.134 (6)° | Block, clear light colourless |
V = 1400.0 (7) Å3 | 0.16 × 0.12 × 0.08 mm |
Data collection top
Bruker APEX-II CCD diffractometer | 3094 reflections with I > 2σ(I) |
φ and ω scans | Rint = 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 = 0.746 | h = −15→15 |
12980 measured reflections | k = −15→15 |
6409 independent reflections | l = −15→16 |
Refinement top
Refinement on F2 | Primary atom site location: dual |
Least-squares matrix: full | Hydrogen site location: mixed |
R[F2 > 2σ(F2)] = 0.064 | H 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 reflections | Δρmax = 0.22 e Å−3 |
390 parameters | Δρmin = −0.26 e Å−3 |
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 | x | y | z | Uiso*/Ueq | Occ. (<1) |
O1 | 0.9399 (2) | 0.33405 (18) | 0.03997 (19) | 0.0661 (5) | |
O2 | 0.4004 (2) | 0.8436 (2) | 0.20077 (18) | 0.0726 (6) | |
O3 | 0.4546 (2) | 0.6491 (2) | 0.52574 (19) | 0.0771 (6) | |
O4 | 0.0972 (2) | 0.2538 (2) | 0.1872 (2) | 0.0812 (7) | |
N1 | 1.2240 (3) | −0.1087 (2) | 0.2728 (2) | 0.0647 (6) | |
N3 | 0.2258 (2) | 0.1555 (2) | 0.0886 (2) | 0.0642 (6) | |
N2 | 0.7056 (2) | 0.2491 (2) | 0.4389 (2) | 0.0666 (6) | |
C12 | 0.4261 (2) | 0.7490 (2) | 0.3647 (2) | 0.0467 (6) | |
H12 | 0.376682 | 0.782242 | 0.389472 | 0.056* | |
C29 | 0.4052 (2) | 0.0871 (2) | 0.0339 (2) | 0.0526 (5) | |
C13 | 0.4754 (3) | 0.6752 (2) | 0.4276 (2) | 0.0536 (6) | |
C1 | 0.8813 (3) | 0.3891 (2) | 0.0875 (3) | 0.0535 (6) | |
C11 | 0.4495 (2) | 0.7735 (2) | 0.2659 (2) | 0.0538 (6) | |
C17 | 1.0452 (3) | −0.0273 (2) | 0.3105 (2) | 0.0559 (6) | |
C22 | 0.8809 (3) | 0.1544 (3) | 0.4155 (2) | 0.0538 (6) | |
C14 | 0.5497 (3) | 0.6278 (2) | 0.3922 (3) | 0.0652 (8) | |
H14 | 0.583521 | 0.578293 | 0.435762 | 0.078* | |
C23 | 0.7404 (3) | 0.0959 (3) | 0.3356 (2) | 0.0596 (7) | |
H23 | 0.701062 | 0.022125 | 0.271152 | 0.072* | |
C24 | 0.6585 (3) | 0.1456 (3) | 0.3504 (2) | 0.0623 (7) | |
H24 | 0.563536 | 0.103825 | 0.294641 | 0.075* | |
C28 | 0.2734 (3) | −0.0033 (2) | 0.0111 (3) | 0.0605 (7) | |
H28 | 0.241504 | −0.090795 | −0.022935 | 0.073* | |
C20 | 0.9472 (3) | 0.0127 (3) | 0.3232 (3) | 0.0607 (7) | |
H20 | 0.853106 | −0.037429 | 0.266235 | 0.073* | |
C21 | 0.9778 (3) | 0.1112 (3) | 0.4060 (2) | 0.0612 (7) | |
H21 | 1.071187 | 0.159069 | 0.465322 | 0.073* | |
C6 | 0.8835 (3) | 0.3850 (3) | 0.1995 (3) | 0.0628 (7) | |
H6 | 0.927142 | 0.343824 | 0.247210 | 0.075* | |
C9 | 0.5747 (3) | 0.6520 (3) | 0.2943 (3) | 0.0728 (9) | |
C16 | 0.9955 (3) | −0.1391 (3) | 0.2225 (3) | 0.0659 (7) | |
H16 | 0.899175 | −0.190105 | 0.172894 | 0.079* | |
C26 | 0.9296 (3) | 0.2608 (3) | 0.5086 (3) | 0.0677 (8) | |
H26 | 1.023885 | 0.303996 | 0.566211 | 0.081* | |
C10 | 0.5251 (3) | 0.7271 (3) | 0.2319 (3) | 0.0696 (8) | |
H10 | 0.543334 | 0.746273 | 0.165788 | 0.084* | |
C30 | 0.4422 (3) | 0.2135 (3) | 0.0822 (3) | 0.0672 (8) | |
H30 | 0.529481 | 0.279956 | 0.097032 | 0.081* | |
C15 | 1.0867 (3) | −0.1755 (3) | 0.2075 (3) | 0.0655 (7) | |
H15 | 1.049755 | −0.252212 | 0.147523 | 0.079* | |
C27 | 0.1890 (3) | 0.0341 (3) | 0.0381 (3) | 0.0673 (8) | |
H27 | 0.099141 | −0.029954 | 0.019849 | 0.081* | |
C31 | 0.3520 (3) | 0.2418 (3) | 0.1083 (3) | 0.0710 (8) | |
H31 | 0.381445 | 0.328622 | 0.142622 | 0.085* | |
C19 | 1.2716 (3) | −0.0027 (3) | 0.3593 (3) | 0.0684 (8) | |
H19 | 1.368389 | 0.045434 | 0.408220 | 0.082* | |
C2 | 0.8167 (3) | 0.4505 (2) | 0.0196 (3) | 0.0697 (8) | |
H2A | 0.814092 | 0.453757 | −0.057200 | 0.084* | |
C18 | 1.1887 (3) | 0.0404 (3) | 0.3813 (3) | 0.0669 (8) | |
H18 | 1.228639 | 0.115660 | 0.444245 | 0.080* | |
C25 | 0.8405 (3) | 0.3032 (3) | 0.5168 (3) | 0.0772 (9) | |
H25 | 0.876730 | 0.375464 | 0.581831 | 0.093* | |
C5 | 0.8203 (3) | 0.4427 (3) | 0.2405 (3) | 0.0851 (10) | |
H5 | 0.821492 | 0.438929 | 0.316771 | 0.102* | |
C3 | 0.7564 (3) | 0.5065 (3) | 0.0649 (4) | 0.0905 (12) | |
H3A | 0.713079 | 0.547949 | 0.017228 | 0.109* | |
C4 | 0.7554 (3) | 0.5059 (3) | 0.1750 (5) | 0.1021 (15) | |
C33 | 0.2080 (4) | 0.3504 (4) | 0.2933 (3) | 0.1029 (12) | |
H33A | 0.245899 | 0.430482 | 0.273412 | 0.154* | |
H33B | 0.280014 | 0.325921 | 0.327327 | 0.154* | |
H33C | 0.174537 | 0.361710 | 0.352464 | 0.154* | |
C8A | 0.6527 (5) | 0.5815 (6) | 0.2804 (5) | 0.0430 (12) | 0.5 |
H8A | 0.683801 | 0.542362 | 0.339544 | 0.052* | 0.5 |
C7A | 0.6764 (5) | 0.5759 (5) | 0.1823 (5) | 0.0423 (11) | 0.5 |
H7A | 0.645413 | 0.613643 | 0.121750 | 0.051* | 0.5 |
C7B | 0.6993 (6) | 0.5456 (5) | 0.2613 (6) | 0.0533 (13) | 0.5 |
H7B | 0.706127 | 0.520530 | 0.332746 | 0.064* | 0.5 |
C8B | 0.6424 (5) | 0.6171 (5) | 0.2232 (7) | 0.0511 (13) | 0.5 |
H8B | 0.643322 | 0.645624 | 0.154644 | 0.061* | 0.5 |
C32 | 0.5048 (3) | 0.0573 (2) | 0.0117 (2) | 0.0526 (5) | |
H32 | 0.583252 | 0.126604 | 0.014276 | 0.063* | |
H2 | 0.344 (3) | 0.856 (3) | 0.225 (3) | 0.093 (11)* | |
H3 | 0.403 (3) | 0.683 (3) | 0.533 (3) | 0.096 (11)* | |
H4 | 0.130 (3) | 0.217 (3) | 0.150 (3) | 0.103 (12)* | |
H1 | 0.988 (3) | 0.303 (3) | 0.087 (3) | 0.102 (13)* | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
O1 | 0.0731 (13) | 0.0676 (12) | 0.0774 (14) | 0.0448 (11) | 0.0424 (11) | 0.0134 (11) |
O2 | 0.0751 (14) | 0.0919 (15) | 0.0731 (13) | 0.0450 (13) | 0.0461 (12) | 0.0388 (12) |
O3 | 0.0972 (16) | 0.0929 (15) | 0.0792 (14) | 0.0699 (14) | 0.0451 (13) | 0.0438 (12) |
O4 | 0.0607 (13) | 0.0718 (14) | 0.0984 (17) | 0.0394 (12) | 0.0196 (13) | 0.0025 (13) |
N1 | 0.0649 (16) | 0.0653 (15) | 0.0674 (15) | 0.0362 (13) | 0.0277 (13) | 0.0178 (13) |
N3 | 0.0509 (14) | 0.0621 (15) | 0.0760 (16) | 0.0303 (12) | 0.0207 (12) | 0.0217 (13) |
N2 | 0.0616 (16) | 0.0880 (17) | 0.0562 (14) | 0.0379 (14) | 0.0312 (13) | 0.0155 (14) |
C12 | 0.0427 (13) | 0.0491 (13) | 0.0502 (14) | 0.0246 (12) | 0.0211 (11) | 0.0075 (11) |
C29 | 0.0425 (10) | 0.0566 (11) | 0.0489 (10) | 0.0168 (9) | 0.0177 (8) | 0.0184 (9) |
C13 | 0.0491 (15) | 0.0547 (15) | 0.0574 (16) | 0.0305 (13) | 0.0192 (13) | 0.0098 (13) |
C1 | 0.0446 (14) | 0.0382 (13) | 0.0715 (18) | 0.0164 (12) | 0.0272 (13) | 0.0021 (12) |
C11 | 0.0416 (14) | 0.0580 (15) | 0.0559 (16) | 0.0197 (13) | 0.0223 (12) | 0.0088 (13) |
C17 | 0.0558 (16) | 0.0553 (15) | 0.0549 (16) | 0.0278 (14) | 0.0219 (14) | 0.0149 (13) |
C22 | 0.0544 (16) | 0.0647 (16) | 0.0443 (14) | 0.0282 (14) | 0.0239 (13) | 0.0173 (13) |
C14 | 0.0449 (15) | 0.0539 (16) | 0.090 (2) | 0.0299 (14) | 0.0208 (15) | 0.0025 (15) |
C23 | 0.0610 (18) | 0.0647 (16) | 0.0488 (15) | 0.0284 (15) | 0.0235 (14) | 0.0097 (13) |
C24 | 0.0521 (16) | 0.082 (2) | 0.0532 (16) | 0.0317 (16) | 0.0243 (14) | 0.0172 (16) |
C28 | 0.0486 (15) | 0.0473 (14) | 0.0783 (19) | 0.0198 (13) | 0.0247 (14) | 0.0176 (14) |
C20 | 0.0543 (16) | 0.0621 (17) | 0.0569 (16) | 0.0254 (14) | 0.0198 (13) | 0.0136 (14) |
C21 | 0.0554 (16) | 0.0681 (17) | 0.0535 (16) | 0.0260 (15) | 0.0228 (14) | 0.0126 (15) |
C6 | 0.0574 (16) | 0.0595 (16) | 0.0730 (19) | 0.0242 (14) | 0.0368 (15) | 0.0106 (14) |
C9 | 0.0334 (14) | 0.0606 (17) | 0.096 (2) | 0.0124 (13) | 0.0227 (16) | −0.0214 (17) |
C16 | 0.0548 (17) | 0.0649 (18) | 0.0615 (17) | 0.0246 (15) | 0.0168 (14) | 0.0071 (15) |
C26 | 0.0544 (17) | 0.081 (2) | 0.0549 (16) | 0.0275 (16) | 0.0213 (14) | 0.0013 (15) |
C10 | 0.0478 (16) | 0.0774 (19) | 0.0705 (19) | 0.0152 (15) | 0.0358 (15) | −0.0037 (16) |
C30 | 0.0464 (16) | 0.0509 (16) | 0.083 (2) | 0.0121 (13) | 0.0215 (15) | 0.0143 (15) |
C15 | 0.068 (2) | 0.0623 (17) | 0.0594 (17) | 0.0343 (16) | 0.0209 (15) | 0.0080 (14) |
C27 | 0.0448 (15) | 0.0561 (17) | 0.094 (2) | 0.0205 (14) | 0.0273 (15) | 0.0269 (16) |
C31 | 0.0581 (18) | 0.0520 (16) | 0.089 (2) | 0.0246 (15) | 0.0221 (16) | 0.0153 (16) |
C19 | 0.0540 (17) | 0.0654 (18) | 0.0710 (19) | 0.0269 (15) | 0.0183 (15) | 0.0061 (16) |
C2 | 0.0602 (17) | 0.0515 (15) | 0.095 (2) | 0.0275 (15) | 0.0317 (17) | 0.0175 (16) |
C18 | 0.0634 (19) | 0.0576 (17) | 0.0688 (18) | 0.0282 (15) | 0.0227 (16) | 0.0044 (15) |
C25 | 0.068 (2) | 0.092 (2) | 0.0655 (19) | 0.0363 (19) | 0.0311 (17) | 0.0005 (17) |
C5 | 0.0610 (19) | 0.076 (2) | 0.095 (2) | 0.0066 (17) | 0.0516 (19) | −0.0194 (19) |
C3 | 0.0524 (18) | 0.0473 (17) | 0.162 (4) | 0.0284 (15) | 0.039 (2) | 0.002 (2) |
C4 | 0.0423 (17) | 0.0515 (18) | 0.179 (4) | 0.0044 (15) | 0.053 (2) | −0.037 (2) |
C33 | 0.072 (2) | 0.104 (3) | 0.095 (3) | 0.041 (2) | 0.008 (2) | −0.001 (2) |
C8A | 0.035 (3) | 0.041 (3) | 0.053 (3) | 0.025 (2) | 0.013 (3) | 0.011 (3) |
C7A | 0.038 (3) | 0.035 (2) | 0.056 (3) | 0.019 (2) | 0.021 (2) | 0.011 (2) |
C7B | 0.048 (3) | 0.049 (3) | 0.058 (4) | 0.024 (3) | 0.019 (3) | 0.012 (3) |
C8B | 0.042 (3) | 0.048 (3) | 0.061 (4) | 0.020 (3) | 0.024 (3) | 0.012 (3) |
C32 | 0.0425 (10) | 0.0566 (11) | 0.0489 (10) | 0.0168 (9) | 0.0177 (8) | 0.0184 (9) |
Geometric parameters (Å, º) top
O1—C1 | 1.358 (3) | C21—H21 | 0.9400 |
O1—H1 | 0.873 (18) | C6—H6 | 0.9400 |
O2—C11 | 1.358 (3) | C6—C5 | 1.382 (4) |
O2—H2 | 0.879 (17) | C9—C10 | 1.396 (4) |
O3—C13 | 1.357 (3) | C9—C8A | 1.514 (6) |
O3—H3 | 0.881 (17) | C9—C8B | 1.515 (7) |
O4—C33 | 1.404 (4) | C16—H16 | 0.9400 |
O4—H4 | 0.886 (18) | C16—C15 | 1.373 (4) |
N1—C15 | 1.327 (4) | C26—H26 | 0.9400 |
N1—C19 | 1.331 (4) | C26—C25 | 1.366 (4) |
N3—C27 | 1.337 (3) | C10—H10 | 0.9400 |
N3—C31 | 1.326 (3) | C30—H30 | 0.9400 |
N2—C24 | 1.327 (3) | C30—C31 | 1.368 (4) |
N2—C25 | 1.334 (4) | C15—H15 | 0.9400 |
C12—H12 | 0.9400 | C27—H27 | 0.9400 |
C12—C13 | 1.384 (3) | C31—H31 | 0.9400 |
C12—C11 | 1.374 (3) | C19—H19 | 0.9400 |
C29—C28 | 1.378 (3) | C19—C18 | 1.367 (4) |
C29—C30 | 1.383 (4) | C2—H2A | 0.9400 |
C29—C32 | 1.460 (4) | C2—C3 | 1.368 (4) |
C13—C14 | 1.383 (3) | C18—H18 | 0.9400 |
C1—C6 | 1.376 (4) | C25—H25 | 0.9400 |
C1—C2 | 1.380 (4) | C5—H5 | 0.9400 |
C11—C10 | 1.381 (4) | C5—C4 | 1.386 (5) |
C17—C20 | 1.466 (4) | C3—H3A | 0.9400 |
C17—C16 | 1.385 (4) | C3—C4 | 1.361 (6) |
C17—C18 | 1.389 (4) | C4—C7A | 1.499 (6) |
C22—C23 | 1.384 (4) | C4—C7B | 1.571 (7) |
C22—C21 | 1.464 (4) | C33—H33A | 0.9700 |
C22—C26 | 1.378 (4) | C33—H33B | 0.9700 |
C14—H14 | 0.9400 | C33—H33C | 0.9700 |
C14—C9 | 1.370 (4) | C8A—H8A | 0.9400 |
C23—H23 | 0.9400 | C8A—C7A | 1.339 (7) |
C23—C24 | 1.374 (4) | C7A—H7A | 0.9400 |
C24—H24 | 0.9400 | C7B—H7B | 0.9400 |
C28—H28 | 0.9400 | C7B—C8B | 1.302 (7) |
C28—C27 | 1.368 (4) | C8B—H8B | 0.9400 |
C20—H20 | 0.9400 | C32—C32i | 1.316 (5) |
C20—C21 | 1.307 (4) | C32—H32 | 0.9400 |
| | | |
C1—O1—H1 | 117 (2) | C11—C10—C9 | 120.9 (3) |
C11—O2—H2 | 109 (2) | C11—C10—H10 | 119.6 |
C13—O3—H3 | 106 (2) | C9—C10—H10 | 119.6 |
C33—O4—H4 | 109 (2) | C29—C30—H30 | 120.0 |
C15—N1—C19 | 116.1 (2) | C31—C30—C29 | 120.1 (3) |
C31—N3—C27 | 114.9 (2) | C31—C30—H30 | 120.0 |
C24—N2—C25 | 115.6 (2) | N1—C15—C16 | 123.9 (3) |
C13—C12—H12 | 120.1 | N1—C15—H15 | 118.1 |
C11—C12—H12 | 120.1 | C16—C15—H15 | 118.1 |
C11—C12—C13 | 119.7 (2) | N3—C27—C28 | 124.4 (2) |
C28—C29—C30 | 115.9 (2) | N3—C27—H27 | 117.8 |
C28—C29—C32 | 124.5 (2) | C28—C27—H27 | 117.8 |
C30—C29—C32 | 119.7 (2) | N3—C31—C30 | 124.6 (3) |
O3—C13—C12 | 121.5 (2) | N3—C31—H31 | 117.7 |
O3—C13—C14 | 118.4 (2) | C30—C31—H31 | 117.7 |
C14—C13—C12 | 120.1 (2) | N1—C19—H19 | 117.9 |
O1—C1—C6 | 122.5 (2) | N1—C19—C18 | 124.1 (3) |
O1—C1—C2 | 118.2 (3) | C18—C19—H19 | 117.9 |
C6—C1—C2 | 119.3 (2) | C1—C2—H2A | 120.2 |
O2—C11—C12 | 121.3 (2) | C3—C2—C1 | 119.5 (3) |
O2—C11—C10 | 118.9 (2) | C3—C2—H2A | 120.2 |
C12—C11—C10 | 119.8 (3) | C17—C18—H18 | 120.1 |
C16—C17—C20 | 119.6 (3) | C19—C18—C17 | 119.9 (3) |
C16—C17—C18 | 116.0 (3) | C19—C18—H18 | 120.1 |
C18—C17—C20 | 124.4 (3) | N2—C25—C26 | 124.4 (3) |
C23—C22—C21 | 124.4 (3) | N2—C25—H25 | 117.8 |
C26—C22—C23 | 116.2 (2) | C26—C25—H25 | 117.8 |
C26—C22—C21 | 119.4 (3) | C6—C5—H5 | 118.3 |
C13—C14—H14 | 119.6 | C6—C5—C4 | 123.5 (3) |
C9—C14—C13 | 120.9 (3) | C4—C5—H5 | 118.3 |
C9—C14—H14 | 119.6 | C2—C3—H3A | 118.1 |
C22—C23—H23 | 120.0 | C4—C3—C2 | 123.9 (3) |
C24—C23—C22 | 120.1 (3) | C4—C3—H3A | 118.1 |
C24—C23—H23 | 120.0 | C5—C4—C7A | 140.9 (5) |
N2—C24—C23 | 123.8 (3) | C5—C4—C7B | 101.1 (4) |
N2—C24—H24 | 118.1 | C3—C4—C5 | 115.1 (3) |
C23—C24—H24 | 118.1 | C3—C4—C7A | 103.9 (4) |
C29—C28—H28 | 120.0 | C3—C4—C7B | 143.7 (4) |
C27—C28—C29 | 120.0 (2) | O4—C33—H33A | 109.5 |
C27—C28—H28 | 120.0 | O4—C33—H33B | 109.5 |
C17—C20—H20 | 116.8 | O4—C33—H33C | 109.5 |
C21—C20—C17 | 126.4 (3) | H33A—C33—H33B | 109.5 |
C21—C20—H20 | 116.8 | H33A—C33—H33C | 109.5 |
C22—C21—H21 | 116.8 | H33B—C33—H33C | 109.5 |
C20—C21—C22 | 126.4 (3) | C9—C8A—H8A | 120.7 |
C20—C21—H21 | 116.8 | C7A—C8A—C9 | 118.7 (6) |
C1—C6—H6 | 120.7 | C7A—C8A—H8A | 120.7 |
C1—C6—C5 | 118.7 (3) | C4—C7A—H7A | 122.1 |
C5—C6—H6 | 120.7 | C8A—C7A—C4 | 115.9 (6) |
C14—C9—C10 | 118.6 (2) | C8A—C7A—H7A | 122.1 |
C14—C9—C8A | 105.9 (4) | C4—C7B—H7B | 123.7 |
C14—C9—C8B | 138.5 (4) | C8B—C7B—C4 | 112.7 (6) |
C10—C9—C8A | 135.6 (4) | C8B—C7B—H7B | 123.7 |
C10—C9—C8B | 102.9 (4) | C9—C8B—H8B | 121.5 |
C17—C16—H16 | 120.0 | C7B—C8B—C9 | 116.9 (7) |
C15—C16—C17 | 120.0 (3) | C7B—C8B—H8B | 121.5 |
C15—C16—H16 | 120.0 | C29—C32—H32 | 116.9 |
C22—C26—H26 | 120.1 | C32i—C32—C29 | 126.3 (3) |
C25—C26—C22 | 119.8 (3) | C32i—C32—H32 | 116.9 |
C25—C26—H26 | 120.1 | | |
Symmetry code: (i) −x+1, −y, −z. |
Hydrogen-bond geometry (Å, º) top
D—H···A | D—H | H···A | D···A | D—H···A |
O2—H2···N1ii | 0.88 (2) | 1.89 (2) | 2.766 (3) | 177 (3) |
O3—H3···N2iii | 0.88 (2) | 1.88 (2) | 2.754 (3) | 175 (3) |
O4—H4···N3 | 0.89 (2) | 1.89 (2) | 2.770 (3) | 172 (3) |
O1—H1···O4iv | 0.87 (2) | 1.76 (2) | 2.626 (3) | 175 (3) |
Symmetry codes: (ii) x−1, y+1, z; (iii) −x+1, −y+1, −z+1; (iv) x+1, y, z. |
Crystal data top
C14H12O3·2(C10H8N4) | F(000) = 2496 |
Mr = 596.64 | Dx = 1.337 Mg m−3 |
Monoclinic, C2/c | Mo Kα radiation, λ = 0.71073 Å |
a = 17.606 (6) Å | Cell parameters from 1043 reflections |
b = 7.969 (3) Å | θ = 2.4–20.8° |
c = 42.568 (14) Å | µ = 0.09 mm−1 |
β = 97.006 (7)° | T = 220 K |
V = 5928 (3) Å3 | Needle, clear orangish orange |
Z = 8 | 0.2 × 0.08 × 0.02 mm |
Data collection top
Bruker APEX-II CCD diffractometer | 2609 reflections with I > 2σ(I) |
φ and ω scans | Rint = 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 = 0.745 | h = −20→15 |
15154 measured reflections | k = −8→9 |
5148 independent reflections | l = −50→50 |
Refinement top
Refinement on F2 | Primary atom site location: structure-invariant direct methods |
Least-squares matrix: full | Hydrogen site location: mixed |
R[F2 > 2σ(F2)] = 0.073 | H 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 reflections | Δρmax = 0.35 e Å−3 |
418 parameters | Δρmin = −0.31 e Å−3 |
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 | x | y | z | Uiso*/Ueq | |
O3 | 0.36308 (17) | −0.0842 (4) | 0.54829 (7) | 0.0372 (8) | |
O2 | 0.3623 (2) | 0.4783 (5) | 0.50795 (7) | 0.0474 (10) | |
O1 | 0.3766 (2) | 0.8777 (5) | 0.74604 (7) | 0.0503 (10) | |
N2 | 0.0715 (2) | 0.4559 (5) | 0.62856 (7) | 0.0358 (10) | |
N1 | 0.1093 (2) | 0.1935 (5) | 0.54587 (7) | 0.0348 (10) | |
N3 | 0.1286 (2) | 0.5238 (5) | 0.64369 (8) | 0.0344 (10) | |
N8 | 0.6353 (2) | 0.1538 (5) | 0.51584 (8) | 0.0383 (10) | |
N5 | 0.6369 (2) | 0.7075 (5) | 0.70086 (8) | 0.0392 (10) | |
N6 | 0.6680 (2) | 0.4601 (5) | 0.61557 (8) | 0.0415 (10) | |
N4 | 0.0964 (2) | 0.7684 (5) | 0.72896 (8) | 0.0440 (11) | |
N7 | 0.6115 (2) | 0.3850 (6) | 0.60305 (8) | 0.0446 (10) | |
C13 | 0.3639 (2) | 0.0842 (6) | 0.55253 (9) | 0.0271 (10) | |
C20 | 0.1132 (2) | 0.6048 (6) | 0.67213 (9) | 0.0317 (11) | |
C17 | 0.0881 (2) | 0.3722 (6) | 0.60029 (9) | 0.0330 (11) | |
C9 | 0.3708 (2) | 0.3206 (6) | 0.58855 (9) | 0.0293 (11) | |
C10 | 0.3679 (2) | 0.4286 (6) | 0.56282 (9) | 0.0299 (11) | |
H10 | 0.369335 | 0.545313 | 0.566058 | 0.036* | |
C3 | 0.3654 (3) | 0.7938 (6) | 0.66238 (9) | 0.0355 (12) | |
H3A | 0.359974 | 0.856548 | 0.643549 | 0.043* | |
C4 | 0.3697 (2) | 0.6221 (6) | 0.66043 (9) | 0.0315 (11) | |
C5 | 0.3786 (2) | 0.5307 (6) | 0.68905 (9) | 0.0315 (11) | |
H5 | 0.382908 | 0.413200 | 0.688629 | 0.038* | |
C1 | 0.3754 (2) | 0.7888 (6) | 0.71915 (9) | 0.0334 (11) | |
C14 | 0.3703 (2) | 0.1503 (6) | 0.58320 (9) | 0.0311 (11) | |
H14 | 0.374402 | 0.076582 | 0.600566 | 0.037* | |
C16 | 0.0277 (2) | 0.2909 (6) | 0.58279 (9) | 0.0352 (12) | |
H16 | −0.021437 | 0.293847 | 0.589263 | 0.042* | |
C8 | 0.3753 (2) | 0.3845 (7) | 0.62127 (9) | 0.0352 (12) | |
H8 | 0.385710 | 0.306524 | 0.637808 | 0.042* | |
C30 | 0.6255 (3) | 0.3042 (6) | 0.57368 (9) | 0.0353 (11) | |
C11 | 0.3630 (2) | 0.3643 (6) | 0.53232 (9) | 0.0308 (11) | |
C6 | 0.3809 (2) | 0.6139 (7) | 0.71785 (9) | 0.0373 (12) | |
H6 | 0.386179 | 0.551685 | 0.736743 | 0.045* | |
C12 | 0.3591 (2) | 0.1948 (6) | 0.52689 (9) | 0.0358 (12) | |
H12 | 0.353351 | 0.153193 | 0.506067 | 0.043* | |
C26 | 0.5816 (3) | 0.5471 (6) | 0.65655 (10) | 0.0372 (12) | |
H26 | 0.538295 | 0.494601 | 0.645730 | 0.045* | |
C27 | 0.6519 (3) | 0.5434 (6) | 0.64450 (10) | 0.0378 (11) | |
C19 | 0.1676 (2) | 0.2716 (6) | 0.56321 (9) | 0.0378 (12) | |
H19 | 0.216469 | 0.263760 | 0.556574 | 0.045* | |
C2 | 0.3686 (2) | 0.8786 (6) | 0.69108 (9) | 0.0381 (12) | |
H2A | 0.366258 | 0.996422 | 0.691427 | 0.046* | |
C24 | 0.1747 (2) | 0.6795 (6) | 0.68970 (9) | 0.0356 (11) | |
H24 | 0.223495 | 0.676029 | 0.682854 | 0.043* | |
C7 | 0.3656 (2) | 0.5455 (6) | 0.62923 (9) | 0.0362 (12) | |
H7 | 0.354498 | 0.619697 | 0.612112 | 0.043* | |
C31 | 0.5608 (2) | 0.2489 (6) | 0.55532 (10) | 0.0383 (12) | |
H31 | 0.512359 | 0.260994 | 0.562250 | 0.046* | |
C23 | 0.1638 (3) | 0.7608 (6) | 0.71786 (10) | 0.0405 (12) | |
H23 | 0.206137 | 0.812624 | 0.729557 | 0.049* | |
C25 | 0.5775 (3) | 0.6296 (7) | 0.68467 (10) | 0.0432 (13) | |
H25 | 0.530327 | 0.631233 | 0.692902 | 0.052* | |
C33 | 0.6988 (3) | 0.2035 (6) | 0.53452 (10) | 0.0414 (12) | |
H33 | 0.746830 | 0.184733 | 0.527591 | 0.050* | |
C32 | 0.5681 (3) | 0.1752 (6) | 0.52652 (10) | 0.0404 (12) | |
H32 | 0.523636 | 0.138519 | 0.513909 | 0.049* | |
C34 | 0.6961 (2) | 0.2802 (6) | 0.56318 (9) | 0.0375 (12) | |
H34 | 0.741244 | 0.315732 | 0.575461 | 0.045* | |
C18 | 0.1600 (2) | 0.3622 (6) | 0.59009 (9) | 0.0356 (12) | |
H18 | 0.202347 | 0.416134 | 0.601324 | 0.043* | |
C28 | 0.7121 (3) | 0.6266 (7) | 0.66048 (10) | 0.0451 (13) | |
H28 | 0.759485 | 0.630192 | 0.652444 | 0.054* | |
C15 | 0.0402 (2) | 0.2068 (6) | 0.55618 (9) | 0.0381 (12) | |
H15 | −0.001836 | 0.154922 | 0.544261 | 0.046* | |
C21 | 0.0423 (3) | 0.6096 (7) | 0.68351 (10) | 0.0450 (13) | |
H21 | −0.001007 | 0.559019 | 0.672274 | 0.054* | |
C22 | 0.0377 (3) | 0.6909 (6) | 0.71173 (10) | 0.0439 (13) | |
H22 | −0.009970 | 0.692367 | 0.719517 | 0.053* | |
C29 | 0.7030 (3) | 0.7054 (7) | 0.68853 (10) | 0.0427 (13) | |
H29 | 0.745349 | 0.760475 | 0.699538 | 0.051* | |
H1 | 0.373 (3) | 0.811 (5) | 0.7622 (8) | 0.055 (16)* | |
H3 | 0.361 (2) | −0.108 (6) | 0.5289 (5) | 0.043 (14)* | |
H2 | 0.363 (3) | 0.427 (6) | 0.4909 (8) | 0.066 (18)* | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
O3 | 0.0448 (19) | 0.036 (2) | 0.0305 (18) | −0.0038 (16) | 0.0048 (14) | −0.0017 (16) |
O2 | 0.082 (3) | 0.039 (2) | 0.0222 (17) | 0.0000 (19) | 0.0119 (16) | 0.0027 (16) |
O1 | 0.086 (3) | 0.045 (2) | 0.0217 (17) | −0.007 (2) | 0.0132 (16) | −0.0063 (17) |
N2 | 0.033 (2) | 0.049 (3) | 0.0258 (19) | 0.0013 (19) | 0.0037 (15) | −0.0079 (18) |
N1 | 0.041 (2) | 0.039 (3) | 0.0253 (19) | 0.0013 (19) | 0.0081 (16) | −0.0004 (18) |
N3 | 0.039 (2) | 0.033 (3) | 0.033 (2) | −0.0066 (18) | 0.0083 (16) | −0.0032 (18) |
N8 | 0.043 (2) | 0.038 (3) | 0.034 (2) | −0.0036 (19) | 0.0054 (17) | −0.0040 (18) |
N5 | 0.049 (2) | 0.040 (3) | 0.029 (2) | 0.000 (2) | 0.0044 (17) | 0.0030 (19) |
N6 | 0.044 (2) | 0.046 (3) | 0.0347 (19) | −0.003 (2) | 0.0036 (17) | 0.0048 (18) |
N4 | 0.050 (3) | 0.048 (3) | 0.034 (2) | 0.002 (2) | 0.0090 (19) | −0.002 (2) |
N7 | 0.050 (2) | 0.049 (3) | 0.0348 (19) | −0.004 (2) | 0.0031 (17) | −0.0003 (19) |
C13 | 0.028 (2) | 0.025 (3) | 0.030 (2) | −0.0002 (19) | 0.0069 (17) | −0.006 (2) |
C20 | 0.031 (2) | 0.037 (3) | 0.028 (2) | 0.002 (2) | 0.0060 (18) | 0.000 (2) |
C17 | 0.033 (2) | 0.044 (3) | 0.023 (2) | 0.000 (2) | 0.0039 (18) | 0.000 (2) |
C9 | 0.023 (2) | 0.036 (3) | 0.029 (2) | 0.000 (2) | 0.0031 (17) | −0.004 (2) |
C10 | 0.035 (2) | 0.029 (3) | 0.026 (2) | −0.003 (2) | 0.0061 (18) | −0.004 (2) |
C3 | 0.050 (3) | 0.036 (3) | 0.021 (2) | 0.005 (2) | 0.0080 (19) | 0.000 (2) |
C4 | 0.029 (2) | 0.042 (3) | 0.024 (2) | −0.001 (2) | 0.0054 (17) | −0.001 (2) |
C5 | 0.033 (2) | 0.029 (3) | 0.033 (2) | 0.002 (2) | 0.0083 (19) | 0.001 (2) |
C1 | 0.039 (3) | 0.033 (3) | 0.027 (2) | −0.005 (2) | 0.0040 (18) | −0.001 (2) |
C14 | 0.034 (2) | 0.032 (3) | 0.028 (2) | −0.003 (2) | 0.0054 (18) | 0.002 (2) |
C16 | 0.031 (2) | 0.049 (3) | 0.028 (2) | −0.003 (2) | 0.0087 (18) | 0.003 (2) |
C8 | 0.034 (3) | 0.047 (4) | 0.025 (2) | −0.001 (2) | 0.0043 (18) | −0.001 (2) |
C30 | 0.044 (2) | 0.035 (3) | 0.029 (2) | −0.003 (2) | 0.0115 (19) | 0.0003 (19) |
C11 | 0.037 (3) | 0.027 (3) | 0.028 (2) | −0.003 (2) | 0.0071 (18) | −0.001 (2) |
C6 | 0.036 (3) | 0.052 (4) | 0.024 (2) | 0.002 (2) | 0.0057 (18) | 0.002 (2) |
C12 | 0.036 (3) | 0.050 (4) | 0.022 (2) | −0.008 (2) | 0.0041 (18) | −0.006 (2) |
C26 | 0.039 (3) | 0.037 (3) | 0.033 (2) | −0.005 (2) | −0.005 (2) | −0.005 (2) |
C27 | 0.049 (3) | 0.038 (3) | 0.027 (2) | 0.004 (2) | 0.0078 (19) | 0.001 (2) |
C19 | 0.034 (3) | 0.053 (4) | 0.028 (2) | 0.002 (2) | 0.0077 (19) | 0.003 (2) |
C2 | 0.049 (3) | 0.039 (3) | 0.027 (2) | −0.006 (2) | 0.0056 (19) | 0.000 (2) |
C24 | 0.036 (3) | 0.037 (3) | 0.035 (2) | −0.003 (2) | 0.0075 (19) | −0.004 (2) |
C7 | 0.037 (3) | 0.046 (4) | 0.026 (2) | −0.002 (2) | 0.0028 (19) | 0.004 (2) |
C31 | 0.033 (3) | 0.045 (3) | 0.038 (3) | 0.001 (2) | 0.007 (2) | −0.006 (2) |
C23 | 0.041 (3) | 0.044 (3) | 0.035 (3) | 0.001 (2) | 0.002 (2) | −0.007 (2) |
C25 | 0.037 (3) | 0.060 (4) | 0.034 (3) | −0.006 (3) | 0.008 (2) | 0.001 (3) |
C33 | 0.039 (3) | 0.049 (4) | 0.037 (3) | 0.004 (2) | 0.006 (2) | 0.002 (2) |
C32 | 0.036 (3) | 0.047 (4) | 0.037 (3) | −0.009 (2) | 0.001 (2) | −0.008 (2) |
C34 | 0.037 (3) | 0.047 (3) | 0.028 (2) | −0.009 (2) | 0.0020 (19) | 0.001 (2) |
C18 | 0.033 (2) | 0.045 (3) | 0.029 (2) | −0.004 (2) | 0.0051 (18) | 0.002 (2) |
C28 | 0.036 (3) | 0.064 (4) | 0.036 (3) | −0.004 (3) | 0.008 (2) | 0.007 (3) |
C15 | 0.034 (3) | 0.050 (4) | 0.030 (2) | −0.010 (2) | 0.0016 (19) | 0.005 (2) |
C21 | 0.039 (3) | 0.064 (4) | 0.032 (2) | −0.006 (3) | 0.004 (2) | −0.011 (3) |
C22 | 0.041 (3) | 0.051 (4) | 0.042 (3) | 0.002 (3) | 0.012 (2) | −0.004 (3) |
C29 | 0.041 (3) | 0.051 (4) | 0.036 (3) | −0.007 (3) | 0.000 (2) | 0.000 (2) |
Geometric parameters (Å, º) top
O3—C13 | 1.354 (5) | C1—C6 | 1.399 (7) |
O3—H3 | 0.846 (19) | C1—C2 | 1.385 (6) |
O2—C11 | 1.378 (5) | C14—H14 | 0.9400 |
O2—H2 | 0.833 (19) | C16—H16 | 0.9400 |
O1—C1 | 1.344 (5) | C16—C15 | 1.357 (6) |
O1—H1 | 0.878 (19) | C8—H8 | 0.9400 |
N2—N3 | 1.249 (5) | C8—C7 | 1.343 (7) |
N2—C17 | 1.437 (5) | C30—C31 | 1.374 (6) |
N1—C19 | 1.342 (6) | C30—C34 | 1.385 (6) |
N1—C15 | 1.347 (5) | C11—C12 | 1.371 (7) |
N3—C20 | 1.426 (5) | C6—H6 | 0.9400 |
N8—C33 | 1.351 (5) | C12—H12 | 0.9400 |
N8—C32 | 1.329 (5) | C26—H26 | 0.9400 |
N5—C25 | 1.333 (6) | C26—C27 | 1.397 (6) |
N5—C29 | 1.334 (6) | C26—C25 | 1.376 (6) |
N6—N7 | 1.224 (5) | C27—C28 | 1.360 (6) |
N6—C27 | 1.457 (6) | C19—H19 | 0.9400 |
N4—C23 | 1.331 (6) | C19—C18 | 1.374 (6) |
N4—C22 | 1.342 (6) | C2—H2A | 0.9400 |
N7—C30 | 1.454 (5) | C24—H24 | 0.9400 |
C13—C14 | 1.400 (5) | C24—C23 | 1.396 (6) |
C13—C12 | 1.397 (6) | C7—H7 | 0.9400 |
C20—C24 | 1.374 (6) | C31—H31 | 0.9400 |
C20—C21 | 1.395 (6) | C31—C32 | 1.379 (6) |
C17—C16 | 1.382 (6) | C23—H23 | 0.9400 |
C17—C18 | 1.390 (6) | C25—H25 | 0.9400 |
C9—C10 | 1.389 (6) | C33—H33 | 0.9400 |
C9—C14 | 1.376 (6) | C33—C34 | 1.371 (6) |
C9—C8 | 1.476 (6) | C32—H32 | 0.9400 |
C10—H10 | 0.9400 | C34—H34 | 0.9400 |
C10—C11 | 1.389 (5) | C18—H18 | 0.9400 |
C3—H3A | 0.9400 | C28—H28 | 0.9400 |
C3—C4 | 1.373 (7) | C28—C29 | 1.376 (6) |
C3—C2 | 1.391 (6) | C15—H15 | 0.9400 |
C4—C5 | 1.411 (6) | C21—H21 | 0.9400 |
C4—C7 | 1.456 (6) | C21—C22 | 1.376 (6) |
C5—H5 | 0.9400 | C22—H22 | 0.9400 |
C5—C6 | 1.390 (6) | C29—H29 | 0.9400 |
| | | |
C13—O3—H3 | 111 (3) | C11—C12—C13 | 119.5 (4) |
C11—O2—H2 | 110 (4) | C11—C12—H12 | 120.2 |
C1—O1—H1 | 110 (3) | C27—C26—H26 | 120.9 |
N3—N2—C17 | 113.6 (3) | C25—C26—H26 | 120.9 |
C19—N1—C15 | 116.4 (4) | C25—C26—C27 | 118.2 (4) |
N2—N3—C20 | 114.2 (3) | C26—C27—N6 | 126.3 (4) |
C32—N8—C33 | 118.0 (4) | C28—C27—N6 | 115.2 (4) |
C25—N5—C29 | 117.2 (4) | C28—C27—C26 | 118.5 (4) |
N7—N6—C27 | 111.1 (4) | N1—C19—H19 | 118.1 |
C23—N4—C22 | 116.4 (4) | N1—C19—C18 | 123.8 (4) |
N6—N7—C30 | 112.2 (4) | C18—C19—H19 | 118.1 |
O3—C13—C14 | 119.7 (4) | C3—C2—H2A | 120.1 |
O3—C13—C12 | 121.5 (4) | C1—C2—C3 | 119.8 (5) |
C12—C13—C14 | 118.8 (4) | C1—C2—H2A | 120.1 |
C24—C20—N3 | 116.1 (4) | C20—C24—H24 | 120.5 |
C24—C20—C21 | 118.6 (4) | C20—C24—C23 | 119.1 (4) |
C21—C20—N3 | 125.3 (4) | C23—C24—H24 | 120.5 |
C16—C17—N2 | 116.6 (4) | C4—C7—H7 | 115.2 |
C16—C17—C18 | 118.3 (4) | C8—C7—C4 | 129.6 (4) |
C18—C17—N2 | 125.0 (4) | C8—C7—H7 | 115.2 |
C10—C9—C8 | 121.5 (4) | C30—C31—H31 | 120.6 |
C14—C9—C10 | 118.8 (4) | C30—C31—C32 | 118.8 (4) |
C14—C9—C8 | 119.7 (4) | C32—C31—H31 | 120.6 |
C9—C10—H10 | 120.0 | N4—C23—C24 | 123.3 (4) |
C11—C10—C9 | 120.1 (4) | N4—C23—H23 | 118.4 |
C11—C10—H10 | 120.0 | C24—C23—H23 | 118.4 |
C4—C3—H3A | 118.6 | N5—C25—C26 | 123.5 (4) |
C4—C3—C2 | 122.7 (4) | N5—C25—H25 | 118.3 |
C2—C3—H3A | 118.6 | C26—C25—H25 | 118.3 |
C3—C4—C5 | 117.6 (4) | N8—C33—H33 | 118.7 |
C3—C4—C7 | 118.4 (4) | N8—C33—C34 | 122.6 (4) |
C5—C4—C7 | 124.0 (5) | C34—C33—H33 | 118.7 |
C4—C5—H5 | 119.9 | N8—C32—C31 | 122.8 (4) |
C6—C5—C4 | 120.2 (5) | N8—C32—H32 | 118.6 |
C6—C5—H5 | 119.9 | C31—C32—H32 | 118.6 |
O1—C1—C6 | 124.4 (4) | C30—C34—H34 | 120.7 |
O1—C1—C2 | 116.9 (4) | C33—C34—C30 | 118.6 (4) |
C2—C1—C6 | 118.7 (4) | C33—C34—H34 | 120.7 |
C13—C14—H14 | 119.2 | C17—C18—H18 | 120.8 |
C9—C14—C13 | 121.6 (4) | C19—C18—C17 | 118.4 (4) |
C9—C14—H14 | 119.2 | C19—C18—H18 | 120.8 |
C17—C16—H16 | 120.3 | C27—C28—H28 | 120.3 |
C15—C16—C17 | 119.3 (4) | C27—C28—C29 | 119.4 (4) |
C15—C16—H16 | 120.3 | C29—C28—H28 | 120.3 |
C9—C8—H8 | 117.5 | N1—C15—C16 | 123.7 (4) |
C7—C8—C9 | 125.0 (4) | N1—C15—H15 | 118.1 |
C7—C8—H8 | 117.5 | C16—C15—H15 | 118.1 |
C31—C30—N7 | 114.6 (4) | C20—C21—H21 | 121.1 |
C31—C30—C34 | 119.2 (4) | C22—C21—C20 | 117.8 (4) |
C34—C30—N7 | 126.2 (4) | C22—C21—H21 | 121.1 |
O2—C11—C10 | 117.0 (4) | N4—C22—C21 | 124.8 (4) |
C12—C11—O2 | 121.8 (4) | N4—C22—H22 | 117.6 |
C12—C11—C10 | 121.2 (4) | C21—C22—H22 | 117.6 |
C5—C6—C1 | 121.0 (4) | N5—C29—C28 | 123.2 (4) |
C5—C6—H6 | 119.5 | N5—C29—H29 | 118.4 |
C1—C6—H6 | 119.5 | C28—C29—H29 | 118.4 |
C13—C12—H12 | 120.2 | | |
Hydrogen-bond geometry (Å, º) top
D—H···A | D—H | H···A | D···A | D—H···A |
O1—H1···N5i | 0.88 (2) | 1.80 (2) | 2.671 (5) | 169 (5) |
O3—H3···N8ii | 0.85 (2) | 1.94 (2) | 2.789 (4) | 176 (4) |
O2—H2···N1iii | 0.83 (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. |