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Acta Cryst. (2009). E65, o185-o186    [ doi:10.1107/S160053680804049X ]

3-(2-Aminoethyl)-2-(4-chloroanilino)quinazolin-4(3H)-one methanol 0.75-solvate

X.-H. Yang, X.-B. Chen and S.-X. Zhou

Abstract top

In the asymmetric unit of the title compound, C16H15ClN4O·0.75CH3OH, there are two independent quinazolin-4(3H)-one molecules and one and a half methanol molecules. One of the methanol molecules is disordered over two positions with equal occupancies. The dihedral angles between the quinazoline ring system and the chlorobenzene ring in the two quinazolin-4(3H)-one molecules are essentially the same, at 39.83 (1) and 39.84 (1)°. Intramolecular N-H...N and O-H...O, and intermolecular N-H...O and N-H...N hydrogen bonds are observed. In addition, [pi]-[pi] stacking interactions, with centroid-to-centroid distances of 3.654 (1), 3.766 (1) and 3.767 (1) Å, and weak C-H...[pi] interactions, are observed.

Comment top

Quinazoline-4(3H)-one derivatives have broad biological properties. Some of these activities include antimicrobial (Pandeya et al., 1999; Shiba et al., 1997), antidiabetic (Malamas & Millen, 1991), anticonvulsant (Mannschreck et al., 1984), antibacterial (Kung et al., 1999), antifungal (Bartroli et al., 1998), protein tyrosine kinase inhibitors (Palmer et al., 1997), EGFR inhibitors (Tsou et al., 2001) and PDGFR phosphorylation inhibitors (Matsuno et al., 2002). We have recently focused on the synthesis of heterocyclic compounds using an aza-Wittig reaction. We have reported the synthesis of the title compound (Yang et al., 2008). We present here the crystal structure of the title compound, (I) (Fig. 1), which can be used as a precursor for obtaining bioactive molecules.

In the crystal structure, there are two quinazolin-4(3H)-one molecules in the asymmetric unit. The quinazoline heterocycle and the adjacent chlorobenzene ring are not planar, but inclined at 39.83 (1)°. Significant intramolecular N—H···N and O—H···O and intermolecular N—H···O and N—H···N hydrogen bonds contribute strongly to the stability of the molecular configuration (Fig. 2 and Table 1). The crystal structure (Fig. 2) is stabilized by weak intermolecular C—H···π hydrogen bonds (Table 1) and by π–π stacking interactions with centroid–centroid separations of 3.654 (1), 3.767 (1) and 3.766 (1) Å for Cg1···Cg5i, Cg2···Cg6ii and Cg3···Cg5i, respectively, where Cg1, Cg2, Cg3, Cg5 and Cg6 are the centroids of rings N2/C7/N3/C8–C10, C1–C6, C9–C14, C17–C22 and C25–C30, respectively [symmetry codes: (i) 1/2 - x, -1/2 + y, 1/2 - z, (ii) 3/2 - x, -1/2 + y, 1/2 - z].

Related literature top

For biological activities of quinazoline-4(3H)-one derivatives, see: Bartroli et al. (1998); Kung et al. (1999); Malamas & Millen (1991); Mannschreck et al. (1984); Matsuno et al. (2002); Palmer et al. (1997); Pandeya et al. (1999); Shiba et al. (1997); Tsou et al. (2001). For synthesis, see: Hu et al. (2006); Yang et al. (2008).

Experimental top

The title compound was prepared according to the literature method (Hu et al., 2006; Yang et al., 2008). Single crystals suitable for X-ray diffraction were obtained from a methanol–dichloromethane (1:1 v/v) solution at room temperature.

Refinement top

One of the methanol solvent molecules was found to be disordered over two positions. Their final occupancies were set to be 0.5:0.5. H atoms bonded to C were placed at calculated positions, with C—H distances of 0.97 and 0.93 Å for H atoms bonded to sp3 and sp2 C atoms, respectively. They were refined using a riding model, with Uiso(H) = 1.2Ueq(C) or 1.5Ueq(methyl C). H atoms bonded to N and O atoms were found in a difference map and then refined with distance restraints of N—H = 0.86 (2) Å and O—H = 0.82 (2) Å, and with Uiso(H) = 1.2Ueq(N) and 1.5Ueq(O).

Computing details top

Data collection: SMART (Bruker, 2000); cell refinement: SAINT (Bruker, 2000); data reduction: SAINT (Bruker, 2000); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXTL (Sheldrick, 2008).

Figures top
[Figure 1] Fig. 1. View of the molecular structure of (I), showing the atom labelling scheme and with displacement ellipsoids drawn at the 50% probability level.
[Figure 2] Fig. 2. A partial view of the crystal packing of (I), showing the formation of N—H···N, O—H···O and N—H···O hydrogen-bonds (dashed lines).
3-(2-Aminoethyl)-2-(4-chloroanilino)quinazolin-4(3H)-one methanol 0.75-solvate top
Crystal data top
C16H15ClN4O·0.75CH4OF(000) = 1420
Mr = 338.81Dx = 1.366 Mg m−3
Monoclinic, P21/nMo Kα radiation, λ = 0.71073 Å
a = 13.380 (3) ÅCell parameters from 5048 reflections
b = 12.048 (2) Åθ = 2.2–25.8°
c = 21.105 (4) ŵ = 0.25 mm−1
β = 104.49 (3)°T = 293 K
V = 3293.8 (11) Å3Block, colourless
Z = 80.23 × 0.20 × 0.10 mm
Data collection top
Bruker SMART APEX CCD area-detector
diffractometer		4529 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tubeRint = 0.018
graphiteθmax = 26.0°, θmin = 2.0°
φ and ω scansh = −16→16
18726 measured reflectionsk = −13→14
6451 independent reflectionsl = −25→23
Refinement top
Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.045Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.132H atoms treated by a mixture of independent and constrained refinement
S = 1.07 w = 1/[σ2(Fo2) + (0.0651P)2 + 0.4596P]
where P = (Fo2 + 2Fc2)/3
6451 reflections(Δ/σ)max = 0.001
453 parametersΔρmax = 0.22 e Å−3
9 restraintsΔρmin = −0.40 e Å−3
Crystal data top
C16H15ClN4O·0.75CH4OV = 3293.8 (11) Å3
Mr = 338.81Z = 8
Monoclinic, P21/nMo Kα radiation
a = 13.380 (3) ŵ = 0.25 mm−1
b = 12.048 (2) ÅT = 293 K
c = 21.105 (4) Å0.23 × 0.20 × 0.10 mm
β = 104.49 (3)°
Data collection top
Bruker SMART APEX CCD area-detector
diffractometer		4529 reflections with I > 2σ(I)
18726 measured reflectionsRint = 0.018
6451 independent reflectionsθmax = 26.0°
Refinement top
R[F2 > 2σ(F2)] = 0.045H atoms treated by a mixture of independent and constrained refinement
wR(F2) = 0.132Δρmax = 0.22 e Å−3
S = 1.07Δρmin = −0.40 e Å−3
6451 reflectionsAbsolute structure: ?
453 parametersFlack parameter: ?
9 restraintsRogers parameter: ?
Special details top

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

Refinement. Refinement of F2 against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F2, conventional R-factors R are based on F, with F set to zero for negative F2. The threshold expression of F2 > σ(F2) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F2 are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/UeqOcc. (<1)
C1−0.08984 (15)0.47979 (16)0.12395 (9)0.0528 (5)
H1−0.03470.46220.10630.063*
C2−0.18874 (15)0.48069 (16)0.08437 (10)0.0556 (5)
H2−0.20030.46360.04020.067*
C3−0.27035 (14)0.50686 (16)0.11023 (10)0.0534 (5)
C4−0.25485 (14)0.53302 (15)0.17510 (10)0.0530 (5)
H4−0.31040.55140.19210.064*
C5−0.15634 (14)0.53178 (14)0.21477 (9)0.0489 (4)
H5−0.14560.54910.25890.059*
C6−0.07211 (14)0.50494 (14)0.18997 (9)0.0458 (4)
C70.11714 (13)0.52077 (14)0.22075 (9)0.0462 (4)
C80.30176 (14)0.52546 (15)0.26820 (10)0.0534 (5)
C90.30837 (13)0.57442 (15)0.20688 (10)0.0499 (4)
C100.21855 (13)0.59011 (14)0.15719 (9)0.0481 (4)
C110.22667 (16)0.63532 (17)0.09793 (10)0.0593 (5)
H110.16750.64670.06440.071*
C120.32126 (18)0.66313 (18)0.08869 (12)0.0688 (6)
H120.32560.69350.04900.083*
C130.41067 (18)0.64669 (19)0.13779 (13)0.0729 (6)
H130.47450.66550.13090.087*
C140.40457 (15)0.60298 (17)0.19601 (12)0.0642 (6)
H140.46450.59180.22890.077*
C150.19411 (16)0.42811 (17)0.32874 (10)0.0621 (5)
H15A0.25860.38900.34570.074*
H15B0.14050.37290.31420.074*
C160.1693 (2)0.4950 (2)0.38362 (11)0.0721 (6)
H16A0.18370.45050.42320.087*
H16B0.21330.56000.39200.087*
C171.20193 (15)0.78133 (15)0.30649 (10)0.0524 (5)
H171.19430.76270.26280.063*
C181.29879 (15)0.78222 (16)0.34860 (10)0.0560 (5)
H181.35650.76490.33350.067*
C191.30922 (15)0.80899 (17)0.41320 (11)0.0572 (5)
C201.22461 (15)0.83549 (17)0.43566 (10)0.0599 (5)
H201.23270.85340.47950.072*
C211.12771 (15)0.83567 (16)0.39363 (10)0.0572 (5)
H211.07060.85440.40910.069*
C221.11498 (14)0.80811 (14)0.32859 (9)0.0478 (4)
C230.92555 (14)0.79103 (14)0.29335 (9)0.0483 (4)
C240.74195 (14)0.78926 (15)0.24330 (10)0.0517 (5)
C250.73119 (14)0.74191 (15)0.30396 (9)0.0486 (4)
C260.81934 (14)0.72442 (15)0.35473 (9)0.0500 (4)
C270.80719 (17)0.67926 (18)0.41340 (11)0.0629 (5)
H270.86490.66650.44770.075*
C280.71130 (18)0.65384 (19)0.42065 (12)0.0708 (6)
H280.70450.62350.45990.085*
C290.62350 (16)0.67269 (18)0.37022 (12)0.0667 (6)
H290.55850.65540.37580.080*
C300.63343 (15)0.71662 (16)0.31264 (11)0.0582 (5)
H300.57490.72990.27890.070*
C310.85432 (16)0.88363 (16)0.18470 (10)0.0604 (5)
H31A0.90880.93770.19970.072*
H31B0.79090.92420.16680.072*
C320.87963 (17)0.81504 (19)0.13073 (10)0.0657 (6)
H32A0.83740.74850.12380.079*
H32B0.86370.85740.09030.079*
C330.5966 (3)0.8449 (4)0.02991 (16)0.1534 (17)
H33A0.65270.89670.03550.230*
H33B0.55030.8552−0.01240.230*
H33C0.62320.77060.03350.230*
Cl1−0.39482 (4)0.50595 (6)0.05930 (3)0.0837 (2)
Cl21.43110 (4)0.81046 (7)0.46778 (3)0.0904 (2)
N10.02479 (12)0.49709 (14)0.23440 (8)0.0541 (4)
H1A0.0250 (17)0.5023 (17)0.2759 (5)0.065*
N20.12216 (11)0.56474 (13)0.16588 (7)0.0486 (4)
N30.20303 (11)0.49523 (12)0.27173 (7)0.0486 (4)
H3A0.5847 (15)0.8370 (17)0.1097 (7)0.215*
N40.06204 (17)0.52954 (17)0.36770 (9)0.0716 (5)
H4A0.0474 (18)0.5956 (11)0.3769 (12)0.086*
H4B0.0261 (17)0.4888 (18)0.3870 (11)0.086*
N51.01963 (12)0.81229 (14)0.28200 (8)0.0553 (4)
H5A1.0179 (16)0.8063 (17)0.2410 (5)0.066*
N60.91717 (11)0.74695 (13)0.34781 (8)0.0524 (4)
N70.84205 (12)0.81837 (12)0.24149 (7)0.0490 (4)
N80.98838 (15)0.78405 (16)0.14741 (9)0.0662 (5)
H8A1.0023 (18)0.7195 (11)0.1344 (11)0.079*
H8B1.0213 (16)0.8306 (15)0.1300 (11)0.079*
O10.37637 (11)0.50823 (12)0.31482 (8)0.0725 (4)
O20.66919 (11)0.80647 (12)0.19558 (7)0.0678 (4)
O30.5479 (2)0.8615 (2)0.07449 (11)0.1432 (10)
C340.5063 (2)0.4916 (2)0.50408 (11)0.131 (2)0.50
H34A0.52280.56780.49810.197*0.50
H34B0.56640.44650.50690.197*0.50
H34C0.48400.48440.54370.197*0.50
O40.4296 (5)0.4506 (6)0.4520 (3)0.168 (2)0.50
H4C0.43240.48270.41830.253*0.50
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
C10.0460 (10)0.0627 (12)0.0515 (12)0.0002 (8)0.0153 (9)−0.0065 (9)
C20.0538 (11)0.0646 (12)0.0466 (11)−0.0023 (9)0.0094 (9)−0.0065 (9)
C30.0412 (10)0.0549 (11)0.0620 (13)−0.0048 (8)0.0086 (9)0.0037 (9)
C40.0465 (10)0.0491 (10)0.0682 (13)−0.0022 (8)0.0232 (9)−0.0019 (9)
C50.0523 (11)0.0473 (10)0.0508 (11)−0.0065 (8)0.0197 (9)−0.0058 (8)
C60.0443 (10)0.0450 (10)0.0478 (11)−0.0036 (7)0.0111 (8)−0.0012 (8)
C70.0424 (10)0.0478 (10)0.0461 (11)0.0011 (7)0.0066 (8)−0.0042 (8)
C80.0464 (11)0.0457 (10)0.0627 (13)0.0047 (8)0.0039 (9)−0.0043 (9)
C90.0450 (10)0.0423 (10)0.0615 (12)0.0009 (8)0.0115 (9)−0.0078 (8)
C100.0462 (10)0.0442 (10)0.0550 (11)0.0008 (8)0.0149 (8)−0.0072 (8)
C110.0618 (12)0.0634 (12)0.0552 (12)−0.0011 (10)0.0191 (10)−0.0021 (10)
C120.0767 (15)0.0650 (13)0.0743 (15)−0.0069 (11)0.0368 (13)−0.0032 (11)
C130.0625 (14)0.0639 (13)0.103 (2)−0.0068 (11)0.0408 (14)−0.0064 (13)
C140.0447 (11)0.0554 (12)0.0912 (17)−0.0010 (9)0.0145 (11)−0.0084 (11)
C150.0648 (13)0.0555 (12)0.0608 (13)0.0046 (9)0.0061 (10)0.0142 (10)
C160.0844 (16)0.0790 (15)0.0473 (12)−0.0093 (12)0.0059 (11)0.0110 (11)
C170.0589 (12)0.0484 (10)0.0532 (11)−0.0026 (8)0.0200 (9)−0.0015 (8)
C180.0488 (11)0.0569 (12)0.0660 (13)0.0018 (8)0.0214 (10)0.0047 (10)
C190.0486 (11)0.0600 (12)0.0617 (13)−0.0071 (9)0.0111 (9)0.0072 (10)
C200.0562 (12)0.0727 (13)0.0518 (12)−0.0147 (10)0.0156 (10)−0.0056 (10)
C210.0522 (11)0.0644 (12)0.0588 (13)−0.0074 (9)0.0208 (10)−0.0108 (10)
C220.0484 (10)0.0424 (10)0.0531 (11)−0.0058 (8)0.0139 (9)0.0006 (8)
C230.0477 (10)0.0442 (10)0.0516 (11)−0.0012 (8)0.0097 (9)−0.0036 (8)
C240.0493 (11)0.0482 (10)0.0549 (12)0.0033 (8)0.0078 (9)−0.0086 (9)
C250.0479 (10)0.0437 (10)0.0534 (11)−0.0010 (8)0.0114 (9)−0.0076 (8)
C260.0483 (10)0.0466 (10)0.0550 (11)−0.0017 (8)0.0128 (9)−0.0042 (8)
C270.0569 (12)0.0735 (14)0.0566 (13)−0.0041 (10)0.0113 (10)0.0064 (10)
C280.0678 (14)0.0782 (15)0.0711 (15)−0.0055 (11)0.0261 (12)0.0073 (12)
C290.0541 (12)0.0679 (14)0.0820 (16)−0.0083 (10)0.0242 (12)−0.0017 (11)
C300.0473 (11)0.0568 (12)0.0678 (14)−0.0025 (9)0.0092 (10)−0.0080 (10)
C310.0619 (12)0.0540 (12)0.0634 (13)0.0021 (9)0.0124 (10)0.0117 (10)
C320.0673 (14)0.0764 (14)0.0520 (12)−0.0076 (11)0.0124 (10)0.0101 (10)
C330.107 (3)0.280 (6)0.075 (2)0.029 (3)0.025 (2)0.000 (3)
Cl10.0437 (3)0.1160 (5)0.0841 (4)−0.0049 (3)0.0024 (3)0.0082 (3)
Cl20.0523 (3)0.1351 (6)0.0773 (4)−0.0083 (3)0.0042 (3)0.0178 (4)
N10.0467 (9)0.0715 (11)0.0437 (9)−0.0048 (7)0.0104 (8)−0.0004 (8)
N20.0438 (8)0.0563 (9)0.0450 (9)0.0024 (7)0.0098 (7)−0.0009 (7)
N30.0474 (9)0.0474 (8)0.0481 (9)0.0028 (6)0.0066 (7)0.0024 (7)
N40.0872 (14)0.0732 (13)0.0557 (11)0.0059 (11)0.0204 (10)0.0053 (10)
N50.0497 (9)0.0676 (10)0.0486 (9)−0.0061 (7)0.0122 (8)−0.0009 (8)
N60.0461 (9)0.0573 (9)0.0524 (10)−0.0024 (7)0.0095 (7)0.0008 (8)
N70.0504 (9)0.0454 (8)0.0503 (9)0.0015 (7)0.0112 (7)0.0008 (7)
N80.0703 (12)0.0699 (12)0.0611 (12)0.0019 (10)0.0214 (9)0.0070 (9)
O10.0518 (8)0.0808 (10)0.0731 (10)0.0075 (7)−0.0065 (8)0.0072 (8)
O20.0562 (8)0.0828 (10)0.0571 (9)0.0043 (7)0.0004 (7)0.0008 (7)
O30.153 (2)0.196 (3)0.0823 (15)0.088 (2)0.0324 (15)0.0356 (16)
C340.187 (7)0.107 (4)0.098 (4)−0.014 (4)0.033 (4)0.004 (3)
O40.170 (6)0.180 (6)0.120 (4)0.016 (4)−0.028 (4)0.018 (4)
Geometric parameters (Å, °) top
C1—C21.377 (3)C20—H200.9300
C1—C61.387 (3)C21—C221.381 (3)
C1—H10.9300C21—H210.9300
C2—C31.374 (3)C22—N51.403 (2)
C2—H20.9300C23—N61.296 (2)
C3—C41.369 (3)C23—N51.363 (2)
C3—Cl11.742 (2)C23—N71.394 (2)
C4—C51.373 (3)C24—O21.231 (2)
C4—H40.9300C24—N71.394 (2)
C5—C61.394 (3)C24—C251.441 (3)
C5—H50.9300C25—C261.397 (3)
C6—N11.400 (2)C25—C301.399 (3)
C7—N21.290 (2)C26—N61.380 (2)
C7—N11.367 (2)C26—C271.399 (3)
C7—N31.398 (2)C27—C281.364 (3)
C8—O11.231 (2)C27—H270.9300
C8—N31.390 (2)C28—C291.392 (3)
C8—C91.445 (3)C28—H280.9300
C9—C101.396 (3)C29—C301.362 (3)
C9—C141.406 (3)C29—H290.9300
C10—N21.381 (2)C30—H300.9300
C10—C111.393 (3)C31—N71.477 (2)
C11—C121.369 (3)C31—C321.513 (3)
C11—H110.9300C31—H31A0.9700
C12—C131.387 (3)C31—H31B0.9700
C12—H120.9300C32—N81.457 (3)
C13—C141.358 (3)C32—H32A0.9700
C13—H130.9300C32—H32B0.9700
C14—H140.9300C33—O31.287 (4)
C15—N31.479 (2)C33—H33A0.9600
C15—C161.514 (3)C33—H33B0.9600
C15—H15A0.9700C33—H33C0.9600
C15—H15B0.9700N1—H1A0.877 (9)
C16—N41.451 (3)N4—H4A0.853 (10)
C16—H16A0.9700N4—H4B0.858 (10)
C16—H16B0.9700N5—H5A0.863 (9)
C17—C181.376 (3)N8—H8A0.861 (10)
C17—C221.395 (3)N8—H8B0.851 (10)
C17—H170.9300O3—H3A0.835 (10)
C18—C191.374 (3)C34—O41.392 (6)
C18—H180.9300C34—H34A0.9600
C19—C201.370 (3)C34—H34B0.9600
C19—Cl21.745 (2)C34—H34C0.9600
C20—C211.376 (3)O4—H4C0.8200
C2—C1—C6120.30 (18)N6—C23—N5121.41 (17)
C2—C1—H1119.8N6—C23—N7124.26 (17)
C6—C1—H1119.8N5—C23—N7114.31 (17)
C3—C2—C1119.97 (18)O2—C24—N7120.26 (19)
C3—C2—H2120.0O2—C24—C25124.01 (18)
C1—C2—H2120.0N7—C24—C25115.72 (17)
C4—C3—C2120.89 (18)C26—C25—C30120.28 (18)
C4—C3—Cl1120.05 (15)C26—C25—C24119.23 (17)
C2—C3—Cl1119.06 (16)C30—C25—C24120.47 (18)
C3—C4—C5119.29 (17)N6—C26—C25122.04 (18)
C3—C4—H4120.4N6—C26—C27119.58 (18)
C5—C4—H4120.4C25—C26—C27118.36 (17)
C4—C5—C6121.07 (17)C28—C27—C26120.5 (2)
C4—C5—H5119.5C28—C27—H27119.8
C6—C5—H5119.5C26—C27—H27119.8
C1—C6—C5118.47 (17)C27—C28—C29121.0 (2)
C1—C6—N1123.70 (17)C27—C28—H28119.5
C5—C6—N1117.66 (16)C29—C28—H28119.5
N2—C7—N1121.83 (16)C30—C29—C28119.57 (19)
N2—C7—N3124.32 (16)C30—C29—H29120.2
N1—C7—N3113.83 (16)C28—C29—H29120.2
O1—C8—N3120.28 (19)C29—C30—C25120.30 (19)
O1—C8—C9124.43 (19)C29—C30—C14101.64 (14)
N3—C8—C9115.28 (17)C25—C30—C14129.96 (14)
C10—C9—C14119.71 (19)C29—C30—H30119.8
C10—C9—C8119.60 (16)C25—C30—H30119.8
C14—C9—C8120.66 (18)N7—C31—C32114.31 (16)
N2—C10—C11119.40 (17)N7—C31—H31A108.7
N2—C10—C9121.80 (17)C32—C31—H31A108.7
C11—C10—C9118.78 (17)N7—C31—H31B108.7
C12—C11—C10120.4 (2)C32—C31—H31B108.7
C12—C11—H11119.8H31A—C31—H31B107.6
C10—C11—H11119.8N8—C32—C31110.86 (18)
C11—C12—C13120.9 (2)N8—C32—H32A109.5
C11—C12—H12119.5C31—C32—H32A109.5
C13—C12—H12119.5N8—C32—H32B109.5
C14—C13—C12119.7 (2)C31—C32—H32B109.5
C14—C13—H13120.1H32A—C32—H32B108.1
C12—C13—H13120.1O3—C33—H33A109.5
C13—C14—C9120.5 (2)O3—C33—H33B109.5
C13—C14—C30103.46 (15)H33A—C33—H33B109.5
C9—C14—C30128.66 (15)O3—C33—H33C109.5
C13—C14—H14119.8H33A—C33—H33C109.5
C9—C14—H14119.8H33B—C33—H33C109.5
N3—C15—C16114.16 (17)C7—N1—C6125.38 (16)
N3—C15—H15A108.7C7—N1—H1A114.7 (15)
C16—C15—H15A108.7C6—N1—H1A115.8 (15)
N3—C15—H15B108.7C7—N2—C10118.03 (16)
C16—C15—H15B108.7C8—N3—C7120.67 (16)
H15A—C15—H15B107.6C8—N3—C15117.26 (16)
N4—C16—C15111.68 (19)C7—N3—C15121.90 (15)
N4—C16—H16A109.3C16—N4—H4A119.0 (17)
C15—C16—H16A109.3C16—N4—H4B111.4 (17)
N4—C16—H16B109.3H4A—N4—H4B104 (2)
C15—C16—H16B109.3C23—N5—C22126.00 (17)
H16A—C16—H16B107.9C23—N5—H5A111.5 (15)
C18—C17—C22120.78 (18)C22—N5—H5A119.4 (15)
C18—C17—H17119.6C23—N6—C26117.98 (16)
C22—C17—H17119.6C23—N7—C24120.39 (16)
C19—C18—C17119.23 (18)C23—N7—C31122.22 (15)
C19—C18—H18120.4C24—N7—C31117.31 (16)
C17—C18—H18120.4C32—N8—H8A115.9 (17)
C20—C19—C18120.71 (19)C32—N8—H8B108.7 (16)
C20—C19—Cl2119.06 (17)H8A—N8—H8B106 (2)
C18—C19—Cl2120.23 (16)C24—O2—O3164.88 (15)
C19—C20—C21120.29 (19)C33—O3—O2110.7 (2)
C19—C20—H20119.9C33—O3—H3A107.5 (17)
C21—C20—H20119.9O4—C34—H34A112.5
C20—C21—C22120.17 (18)O4—C34—H34B106.7
C20—C21—H21119.9H34A—C34—H34B109.5
C22—C21—H21119.9O4—C34—H34C109.1
C21—C22—C17118.83 (18)H34A—C34—H34C109.5
C21—C22—N5123.52 (17)H34B—C34—H34C109.5
C17—C22—N5117.52 (17)
C6—C1—C2—C30.2 (3)C28—C29—C30—C250.5 (3)
C1—C2—C3—C40.5 (3)C28—C29—C30—C14152.10 (18)
C1—C2—C3—Cl1−179.32 (15)C26—C25—C30—C29−1.3 (3)
C2—C3—C4—C5−0.7 (3)C24—C25—C30—C29−179.48 (18)
Cl1—C3—C4—C5179.06 (14)C26—C25—C30—C14−143.90 (15)
C3—C4—C5—C60.3 (3)C24—C25—C30—C1437.9 (2)
C2—C1—C6—C5−0.5 (3)C13—C14—C30—C29178.95 (18)
C2—C1—C6—N1174.61 (17)C9—C14—C30—C2929.7 (2)
C4—C5—C6—C10.3 (3)C13—C14—C30—C25−33.4 (2)
C4—C5—C6—N1−175.16 (16)C9—C14—C30—C25177.3 (2)
O1—C8—C9—C10179.95 (17)N7—C31—C32—N8−78.3 (2)
N3—C8—C9—C101.3 (2)N2—C7—N1—C67.5 (3)
O1—C8—C9—C142.1 (3)N3—C7—N1—C6−173.77 (16)
N3—C8—C9—C14−176.57 (16)C1—C6—N1—C735.7 (3)
C14—C9—C10—N2−179.09 (16)C5—C6—N1—C7−149.14 (18)
C8—C9—C10—N23.0 (3)N1—C7—N2—C10177.40 (16)
C14—C9—C10—C11−0.8 (3)N3—C7—N2—C10−1.2 (3)
C8—C9—C10—C11−178.69 (17)C11—C10—N2—C7178.56 (17)
N2—C10—C11—C12178.72 (17)C9—C10—N2—C7−3.2 (3)
C9—C10—C11—C120.4 (3)O1—C8—N3—C7175.92 (16)
C10—C11—C12—C130.2 (3)C9—C8—N3—C7−5.4 (2)
C11—C12—C13—C14−0.3 (3)O1—C8—N3—C15−8.7 (3)
C12—C13—C14—C9−0.1 (3)C9—C8—N3—C15170.03 (16)
C12—C13—C14—C30−152.49 (18)N2—C7—N3—C85.7 (3)
C10—C9—C14—C130.7 (3)N1—C7—N3—C8−172.99 (15)
C8—C9—C14—C13178.53 (18)N2—C7—N3—C15−169.51 (18)
C10—C9—C14—C30145.43 (15)N1—C7—N3—C1511.8 (2)
C8—C9—C14—C30−36.7 (2)C16—C15—N3—C897.6 (2)
N3—C15—C16—N475.0 (2)C16—C15—N3—C7−87.0 (2)
C22—C17—C18—C190.5 (3)N6—C23—N5—C22−11.2 (3)
C17—C18—C19—C20−0.5 (3)N7—C23—N5—C22170.10 (16)
C17—C18—C19—Cl2179.84 (14)C21—C22—N5—C23−33.2 (3)
C18—C19—C20—C210.0 (3)C17—C22—N5—C23151.00 (17)
Cl2—C19—C20—C21179.59 (15)N5—C23—N6—C26−177.79 (16)
C19—C20—C21—C220.6 (3)N7—C23—N6—C260.8 (3)
C20—C21—C22—C17−0.6 (3)C25—C26—N6—C233.6 (3)
C20—C21—C22—N5−176.36 (18)C27—C26—N6—C23−178.51 (18)
C18—C17—C22—C210.0 (3)N6—C23—N7—C24−6.1 (3)
C18—C17—C22—N5176.04 (16)N5—C23—N7—C24172.51 (15)
O2—C24—C25—C26179.05 (18)N6—C23—N7—C31170.51 (17)
N7—C24—C25—C26−2.5 (2)N5—C23—N7—C31−10.8 (2)
O2—C24—C25—C30−2.7 (3)O2—C24—N7—C23−174.86 (16)
N7—C24—C25—C30175.71 (16)C25—C24—N7—C236.6 (2)
C30—C25—C26—N6179.15 (16)O2—C24—N7—C318.3 (3)
C24—C25—C26—N6−2.6 (3)C25—C24—N7—C31−170.18 (15)
C30—C25—C26—C271.3 (3)C32—C31—N7—C2386.7 (2)
C24—C25—C26—C27179.46 (17)C32—C31—N7—C24−96.5 (2)
N6—C26—C27—C28−178.38 (19)N7—C24—O2—O35.4 (6)
C25—C26—C27—C28−0.4 (3)C25—C24—O2—O3−176.2 (4)
C26—C27—C28—C29−0.4 (3)C24—O2—O3—C3330.1 (7)
C27—C28—C29—C300.4 (3)
Hydrogen-bond geometry (Å, °) top
D—H···AD—HH···AD···AD—H···A
N5—H5A···N80.86 (1)1.93 (1)2.787 (3)170 (2)
O4—H4C···O10.822.152.889 (6)151
O3—H3A···O20.84 (1)1.92 (1)2.744 (3)170 (2)
N1—H1A···N40.88 (1)1.90 (1)2.760 (3)164 (2)
N8—H8B···O4i0.85 (1)2.47 (1)3.284 (8)161 (2)
N8—H8A···N2ii0.86 (1)2.44 (2)3.160 (2)142 (2)
N4—H4B···O3iii0.86 (1)2.10 (1)2.941 (3)168 (2)
N4—H4A···N6iv0.85 (1)2.49 (2)3.223 (3)144 (2)
C5—H5···Cg4iv0.932.813.375 (2)120
C17—H17···Cg1ii0.932.843.459 (2)125
C32—H32A···Cg2ii0.972.983.824 (3)146
Symmetry codes: (i) −x+3/2, y+1/2, −z+1/2; (ii) x+1, y, z; (iii) −x+1/2, y−1/2, −z+1/2; (iv) x−1, y, z.
Table 1
Hydrogen-bond geometry (Å, °) top
D—H···AD—HH···AD···AD—H···A
N5—H5A···N80.86 (1)1.93 (1)2.787 (3)170 (2)
O4—H4C···O10.822.152.889 (6)151
O3—H3A···O20.84 (1)1.92 (1)2.744 (3)170 (2)
N1—H1A···N40.88 (1)1.90 (1)2.760 (3)164 (2)
N8—H8B···O4i0.85 (1)2.47 (1)3.284 (8)161 (2)
N8—H8A···N2ii0.86 (1)2.44 (2)3.160 (2)142 (2)
N4—H4B···O3iii0.86 (1)2.10 (1)2.941 (3)168 (2)
N4—H4A···N6iv0.85 (1)2.49 (2)3.223 (3)144 (2)
C5—H5···Cg4iv0.932.813.375 (2)120
C17—H17···Cg1ii0.932.843.459 (2)125
C32—H32A···Cg2ii0.972.983.824 (3)146
Symmetry codes: (i) −x+3/2, y+1/2, −z+1/2; (ii) x+1, y, z; (iii) −x+1/2, y−1/2, −z+1/2; (iv) x−1, y, z.
Acknowledgements top

The authors gratefully acknowledge financial support of this work by Xianning College, and acknowledge the Sophisticated Analytical Instrument Facility, Central China Normal University, Whuhan, for the data collection.

references
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