organic compounds\(\def\hfill{\hskip 5em}\def\hfil{\hskip 3em}\def\eqno#1{\hfil {#1}}\)

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ISSN: 2056-9890

2-{(E)-[4-(Di­phenyl­amino)­phen­yl]imino­meth­yl}phenol

aDepartment of Chemistry, Bengbu Medical College, Bengbu 233030, People's Republic of China, bDepartment of Chemistry, Anhui University, Hefei 230039, People's Republic of China, and cKey Laboratory of Functional Inorganic Materials, Chemistry, Hefei 230039, People's Republic of China
*Correspondence e-mail: jywu1957@163.com

(Received 17 January 2014; accepted 12 February 2014; online 15 February 2014)

The asymmetric unit of the title Schiff base molecule, C25H20N2O, contains two independent mol­ecules. In each mol­ecule, the C=N bond is in an E conformation. The most significant difference between the two mol­ecules is seen for the dihedral angles between the meth­oxy-substituted benzene ring and the two phenyl rings, which are 85.5 (1) and 82.3 (1)° in the first mol­ecule, and 49.0 (1) and 40.4 (1)° in the second. This conformational difference is reflected in the central C=N—C C torsion angle, which is 28.7 (2)° in the first mol­ecule and −29.8 (3)° in the other. In each mol­ecule, there is an intra­molecular O—H⋯N hydrogen bond.

Related literature

For related structures, see: Damous et al. (2013[Damous, M., Dénès, G., Bouacida, S., Hamlaoui, M., Merazig, H. & Daran, J.-C. (2013). Acta Cryst. E69, o1460-o1461.]); Zheng (2013[Zheng, Y.-F. (2013). Acta Cryst. E69, o1349.]).

[Scheme 1]

Experimental

Crystal data
  • C25H20N2O

  • Mr = 364.43

  • Monoclinic, P 21 /c

  • a = 18.4128 (4) Å

  • b = 21.2523 (4) Å

  • c = 10.2080 (2) Å

  • β = 99.834 (1)°

  • V = 3935.84 (14) Å3

  • Z = 8

  • Mo Kα radiation

  • μ = 0.08 mm−1

  • T = 298 K

  • 0.30 × 0.20 × 0.20 mm

Data collection
  • Bruker SMART CCD diffractometer

  • Absorption correction: multi-scan (SADABS; Sheldrick, 1996[Sheldrick, G. M. (1996). SADABS. University of Göttingen, Germany.]) Tmin = 0.978, Tmax = 0.985

  • 65034 measured reflections

  • 8961 independent reflections

  • 6499 reflections with I > 2σ(I)

  • Rint = 0.029

Refinement
  • R[F2 > 2σ(F2)] = 0.049

  • wR(F2) = 0.181

  • S = 1.09

  • 8961 reflections

  • 507 parameters

  • H-atom parameters constrained

  • Δρmax = 0.13 e Å−3

  • Δρmin = −0.18 e Å−3

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A D—H H⋯A DA D—H⋯A
O1—H1⋯N2 0.82 1.88 2.609 (2) 147
O2—H2⋯N4 0.82 1.86 2.590 (2) 148

Data collection: SMART (Bruker, 2002[Bruker (2002). SMART and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.]); cell refinement: SAINT (Bruker, 2002[Bruker (2002). SMART and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.]); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); molecular graphics: SHELXTL (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); software used to prepare material for publication: SHELXTL.

Supporting information


Comment top

Schiff bases are considered important compounds because of their wide range of biological activities, and also because of their use as ligands in conjunction with transition metals (Damous et al., 2013). Schiff bases derived from salicyladehyde and methylaniline with various substituents have exhibited potential application in pharmaceutical fields for their antitumor, antimicrobial and antiviral activities (Zheng et al., 2013). Herein, with we report the crystal structure of the title compound (I).

In (I) (Fig.1), the Schiff base moiety shows an E configuration about the C16N2 and C19C20 bonds. The most significant difference between the two molecules are the dihedral angles between the methoxy-substituted benzene ring and the two phenyl rings, which are 85.5 (1)° [C20-C25/C1-C6] and 82.3 (1)° [C20-C25/C7-C12] in one molecule and 49.0 (1)° [C40-C50C26-C31] and 40.4 (1)° [C45-C50/C32-C37] in the other. This conformational difference is reflected in the central CN—CC torsion angle which is 28.7 (2)° in one molecule [C19-N2-C16-C15] and -29.8 (3)° [C44-N4-C41-C40] in the other. The bond distances of the two independent molecules are the same within experimental error.

Related literature top

For related structures, see: Damous et al. (2013); Zheng (2013).

Experimental top

A solution of N1,N1-diphenylbenzene-1,4-diamine (13.00 g, 50 ammol) in 30 ml of ethanol was mixed with 2-hydroxybenzaldehyde (9.15 g, 75 mmol) in ethanol 5 ml. The mixture was refluxed for 4h under cooling to room temperature, the soild was filtrated and recrystallized from ethnol to give X-ray quality crystals. Yield: 85%. 1H NMR (400 MHz, d6-(CD3)2CO) 6.99 (t, 2H), 7.12 (m, 8H), 7.36 (t, 4H), 7.41 (d, 3H), 7.59 (d, 1H), 8.93(d, 1H), 13.28 (s, 1H).

Refinement top

All hydrogen atoms were placed in geometrically idealized positions and constrained to ride on their parent atoms, with C—H = 0.93 Å, O—H = 0.82Å and Uiso(H) = 1.2Ueq(C) or 1.5Ueq(O).

Computing details top

Data collection: SMART (Bruker, 2002); cell refinement: SAINT (Bruker, 2002); data reduction: SAINT (Bruker, 2002); 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. The molecular structure of (I). Displacement ellipsoids are drawn at the 30% probability level.
2-{(E)-[4-(Diphenylamino)phenyl]iminomethyl}phenol top
Crystal data top
C25H20N2OF(000) = 1536
Mr = 364.43Dx = 1.230 Mg m3
Monoclinic, P21/cMo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybcCell parameters from 9854 reflections
a = 18.4128 (4) Åθ = 2.2–24.7°
b = 21.2523 (4) ŵ = 0.08 mm1
c = 10.2080 (2) ÅT = 298 K
β = 99.834 (1)°Block, yellow
V = 3935.84 (14) Å30.30 × 0.20 × 0.20 mm
Z = 8
Data collection top
Bruker SMART CCD
diffractometer
8961 independent reflections
Radiation source: fine-focus sealed tube6499 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.029
φ and ω scansθmax = 27.4°, θmin = 2.2°
Absorption correction: multi-scan
(SADABS; Sheldrick, 1996)
h = 2318
Tmin = 0.978, Tmax = 0.985k = 2723
65034 measured reflectionsl = 1313
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)] = 0.049Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.181H-atom parameters constrained
S = 1.09 w = 1/[σ2(Fo2) + (0.1P)2 + 0.5243P]
where P = (Fo2 + 2Fc2)/3
8961 reflections(Δ/σ)max = 0.001
507 parametersΔρmax = 0.13 e Å3
0 restraintsΔρmin = 0.18 e Å3
Crystal data top
C25H20N2OV = 3935.84 (14) Å3
Mr = 364.43Z = 8
Monoclinic, P21/cMo Kα radiation
a = 18.4128 (4) ŵ = 0.08 mm1
b = 21.2523 (4) ÅT = 298 K
c = 10.2080 (2) Å0.30 × 0.20 × 0.20 mm
β = 99.834 (1)°
Data collection top
Bruker SMART CCD
diffractometer
8961 independent reflections
Absorption correction: multi-scan
(SADABS; Sheldrick, 1996)
6499 reflections with I > 2σ(I)
Tmin = 0.978, Tmax = 0.985Rint = 0.029
65034 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0490 restraints
wR(F2) = 0.181H-atom parameters constrained
S = 1.09Δρmax = 0.13 e Å3
8961 reflectionsΔρmin = 0.18 e Å3
507 parameters
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*/Ueq
N20.65015 (7)0.18511 (7)0.70724 (14)0.0475 (3)
O10.52431 (8)0.12577 (8)0.67606 (13)0.0767 (4)
H10.56570.13590.71300.115*
C350.71752 (14)0.54098 (15)1.1730 (2)0.0880 (8)
H350.72290.55541.26020.106*
N40.41701 (8)0.39242 (7)0.52112 (15)0.0553 (4)
N10.91196 (7)0.25341 (7)1.04786 (15)0.0546 (4)
O20.28230 (8)0.36766 (9)0.54581 (15)0.0775 (4)
H20.32370.38290.56510.116*
N30.69482 (8)0.47621 (8)0.77970 (15)0.0589 (4)
C160.71657 (8)0.20425 (7)0.78898 (16)0.0440 (3)
C130.84654 (8)0.23704 (7)0.96105 (16)0.0455 (4)
C200.56131 (8)0.19141 (8)0.50738 (16)0.0462 (4)
C70.96755 (8)0.20695 (8)1.08522 (17)0.0463 (4)
C190.63139 (9)0.20661 (8)0.58888 (17)0.0483 (4)
H190.66390.23280.55430.058*
C10.92484 (9)0.31669 (7)1.09053 (16)0.0467 (4)
C320.70191 (10)0.49776 (9)0.91339 (18)0.0550 (4)
C450.33276 (10)0.34029 (8)0.35242 (19)0.0557 (4)
C150.74933 (9)0.26249 (8)0.77910 (17)0.0518 (4)
H150.72770.29110.71520.062*
C390.62060 (9)0.40697 (8)0.61860 (18)0.0537 (4)
H390.66340.38780.60160.064*
C260.75879 (9)0.47338 (8)0.71989 (17)0.0489 (4)
C81.00166 (10)0.20185 (9)1.21639 (18)0.0573 (4)
H80.98750.22791.28070.069*
C250.50993 (9)0.15246 (9)0.55383 (17)0.0545 (4)
C210.54279 (10)0.21685 (9)0.38024 (18)0.0581 (4)
H210.57680.24220.34750.070*
C170.74919 (9)0.16321 (8)0.88735 (16)0.0470 (4)
H170.72760.12420.89610.056*
C400.55297 (10)0.38645 (9)0.55257 (18)0.0549 (4)
H400.55070.35400.49090.066*
C380.62562 (9)0.45600 (8)0.71015 (17)0.0512 (4)
C180.81303 (9)0.17920 (8)0.97237 (17)0.0482 (4)
H180.83380.15101.03780.058*
C120.98805 (9)0.16712 (8)0.99112 (18)0.0528 (4)
H120.96480.16990.90300.063*
C20.86863 (10)0.35225 (8)1.12765 (18)0.0535 (4)
H2A0.82230.33451.12590.064*
C111.04306 (10)0.12317 (9)1.0277 (2)0.0616 (5)
H111.05660.09630.96400.074*
C140.81354 (9)0.27842 (8)0.86274 (18)0.0533 (4)
H140.83520.31730.85350.064*
C60.99364 (10)0.34357 (9)1.0969 (2)0.0612 (5)
H61.03200.32031.07270.073*
C440.40457 (10)0.36586 (9)0.40703 (19)0.0580 (4)
H440.44250.36290.35790.070*
C410.48819 (9)0.41398 (9)0.57765 (17)0.0524 (4)
C500.27411 (10)0.34239 (9)0.4237 (2)0.0612 (5)
C91.05702 (11)0.15786 (11)1.2517 (2)0.0680 (5)
H91.08020.15481.33980.082*
C270.75680 (10)0.49235 (9)0.58993 (19)0.0574 (4)
H270.71280.50630.53970.069*
C430.56070 (10)0.48410 (10)0.73322 (19)0.0606 (5)
H430.56280.51770.79220.073*
C310.82527 (10)0.45261 (9)0.7935 (2)0.0595 (5)
H310.82740.43960.88110.071*
C300.88793 (11)0.45130 (9)0.7362 (3)0.0705 (6)
H300.93220.43750.78560.085*
C280.82003 (12)0.49053 (10)0.5349 (2)0.0696 (5)
H280.81830.50330.44730.083*
C460.32167 (12)0.31212 (11)0.2265 (2)0.0757 (6)
H460.36020.31080.17840.091*
C290.88547 (12)0.47023 (10)0.6072 (3)0.0732 (6)
H290.92780.46930.56900.088*
C30.88131 (12)0.41414 (10)1.1674 (2)0.0673 (5)
H30.84300.43801.19020.081*
C220.47585 (12)0.20549 (11)0.3023 (2)0.0676 (5)
H220.46450.22300.21780.081*
C420.49353 (10)0.46248 (10)0.6692 (2)0.0605 (5)
H420.45060.48090.68790.073*
C240.44245 (10)0.14073 (12)0.4740 (2)0.0704 (6)
H240.40850.11440.50420.084*
C101.07792 (10)0.11884 (10)1.1578 (2)0.0666 (5)
H101.11540.08961.18190.080*
C230.42569 (11)0.16797 (12)0.3502 (2)0.0726 (6)
H230.37980.16080.29830.087*
C370.74217 (11)0.55151 (10)0.9510 (2)0.0651 (5)
H370.76420.57340.88930.078*
C330.66962 (13)0.46571 (11)1.0058 (2)0.0724 (6)
H330.64270.42930.98140.087*
C40.94920 (14)0.44041 (10)1.1734 (3)0.0803 (6)
H40.95740.48201.20040.096*
C360.74966 (13)0.57282 (12)1.0814 (2)0.0815 (7)
H360.77680.60911.10660.098*
C51.00554 (13)0.40513 (11)1.1393 (3)0.0801 (7)
H51.05220.42281.14470.096*
C490.20642 (12)0.31691 (12)0.3675 (3)0.0850 (7)
H490.16710.31860.41370.102*
C470.25461 (16)0.28644 (12)0.1733 (3)0.0941 (8)
H470.24780.26730.09020.113*
C340.67742 (15)0.48791 (15)1.1355 (2)0.0883 (8)
H340.65510.46641.19740.106*
C480.19746 (14)0.28941 (13)0.2448 (3)0.0976 (9)
H480.15190.27240.20860.117*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
N20.0392 (7)0.0522 (8)0.0498 (8)0.0011 (6)0.0035 (6)0.0029 (6)
O10.0643 (8)0.1061 (12)0.0574 (8)0.0312 (8)0.0041 (6)0.0169 (8)
C350.0838 (16)0.117 (2)0.0560 (12)0.0424 (15)0.0093 (11)0.0196 (14)
N40.0454 (7)0.0602 (9)0.0582 (9)0.0063 (6)0.0029 (6)0.0003 (7)
N10.0470 (7)0.0417 (7)0.0671 (9)0.0048 (6)0.0129 (6)0.0055 (7)
O20.0627 (8)0.0956 (12)0.0762 (10)0.0009 (8)0.0177 (7)0.0033 (8)
N30.0485 (8)0.0746 (10)0.0523 (8)0.0128 (7)0.0052 (6)0.0119 (7)
C160.0364 (7)0.0464 (8)0.0484 (8)0.0006 (6)0.0043 (6)0.0021 (7)
C130.0415 (8)0.0411 (8)0.0505 (9)0.0025 (6)0.0017 (6)0.0028 (7)
C200.0411 (8)0.0505 (9)0.0462 (8)0.0019 (6)0.0054 (6)0.0053 (7)
C70.0381 (7)0.0426 (8)0.0556 (9)0.0010 (6)0.0006 (6)0.0021 (7)
C190.0412 (8)0.0530 (9)0.0507 (9)0.0044 (7)0.0079 (7)0.0017 (7)
C10.0483 (8)0.0418 (8)0.0469 (8)0.0017 (6)0.0012 (7)0.0014 (7)
C320.0509 (9)0.0603 (10)0.0511 (9)0.0002 (8)0.0010 (7)0.0055 (8)
C450.0487 (9)0.0498 (10)0.0647 (11)0.0001 (7)0.0010 (8)0.0008 (8)
C150.0522 (9)0.0434 (9)0.0548 (10)0.0044 (7)0.0051 (7)0.0049 (7)
C390.0464 (9)0.0543 (10)0.0596 (10)0.0001 (7)0.0067 (7)0.0062 (8)
C260.0464 (8)0.0418 (8)0.0571 (10)0.0062 (7)0.0046 (7)0.0027 (7)
C80.0530 (9)0.0629 (11)0.0530 (10)0.0075 (8)0.0001 (8)0.0029 (8)
C250.0464 (9)0.0667 (11)0.0500 (9)0.0082 (8)0.0074 (7)0.0037 (8)
C210.0576 (10)0.0627 (11)0.0527 (10)0.0075 (8)0.0055 (8)0.0019 (8)
C170.0459 (8)0.0429 (8)0.0511 (9)0.0043 (7)0.0052 (7)0.0030 (7)
C400.0517 (9)0.0536 (10)0.0576 (10)0.0033 (7)0.0046 (8)0.0090 (8)
C380.0467 (9)0.0546 (10)0.0509 (9)0.0070 (7)0.0045 (7)0.0031 (7)
C180.0498 (9)0.0407 (8)0.0507 (9)0.0024 (7)0.0009 (7)0.0056 (7)
C120.0527 (9)0.0535 (10)0.0501 (9)0.0021 (7)0.0032 (7)0.0005 (8)
C20.0507 (9)0.0490 (9)0.0596 (10)0.0017 (7)0.0057 (7)0.0010 (8)
C110.0525 (10)0.0597 (11)0.0734 (12)0.0094 (8)0.0130 (9)0.0049 (9)
C140.0529 (9)0.0380 (8)0.0637 (10)0.0046 (7)0.0048 (8)0.0051 (7)
C60.0512 (10)0.0577 (11)0.0738 (12)0.0053 (8)0.0085 (9)0.0066 (9)
C440.0460 (9)0.0674 (12)0.0600 (11)0.0042 (8)0.0076 (8)0.0023 (9)
C410.0450 (8)0.0571 (10)0.0537 (9)0.0073 (7)0.0047 (7)0.0001 (8)
C500.0475 (9)0.0579 (11)0.0757 (13)0.0002 (8)0.0039 (8)0.0104 (10)
C90.0566 (10)0.0810 (14)0.0599 (11)0.0139 (10)0.0090 (9)0.0049 (10)
C270.0554 (10)0.0523 (10)0.0636 (11)0.0042 (8)0.0074 (8)0.0057 (8)
C430.0554 (10)0.0631 (11)0.0630 (11)0.0019 (8)0.0092 (8)0.0172 (9)
C310.0565 (10)0.0492 (10)0.0684 (11)0.0023 (8)0.0019 (9)0.0008 (8)
C300.0488 (10)0.0493 (10)0.1082 (18)0.0018 (8)0.0011 (10)0.0123 (11)
C280.0740 (13)0.0618 (12)0.0772 (13)0.0143 (10)0.0252 (11)0.0013 (10)
C460.0661 (12)0.0793 (14)0.0757 (14)0.0055 (10)0.0050 (10)0.0161 (12)
C290.0601 (12)0.0543 (11)0.1110 (19)0.0119 (9)0.0310 (12)0.0178 (12)
C30.0758 (13)0.0549 (11)0.0682 (12)0.0126 (9)0.0038 (10)0.0106 (9)
C220.0696 (12)0.0754 (13)0.0517 (10)0.0030 (10)0.0071 (9)0.0001 (9)
C420.0463 (9)0.0679 (12)0.0672 (11)0.0000 (8)0.0097 (8)0.0129 (9)
C240.0500 (10)0.0926 (16)0.0674 (13)0.0241 (10)0.0064 (9)0.0085 (11)
C100.0463 (9)0.0671 (12)0.0825 (14)0.0162 (8)0.0002 (9)0.0043 (11)
C230.0538 (10)0.0930 (16)0.0644 (12)0.0107 (10)0.0088 (9)0.0120 (11)
C370.0570 (10)0.0642 (12)0.0691 (12)0.0007 (9)0.0039 (9)0.0094 (10)
C330.0802 (14)0.0755 (14)0.0623 (12)0.0020 (11)0.0149 (10)0.0035 (10)
C40.0904 (16)0.0478 (11)0.0958 (17)0.0088 (11)0.0037 (13)0.0152 (11)
C360.0690 (13)0.0803 (15)0.0833 (16)0.0147 (11)0.0211 (12)0.0294 (13)
C50.0685 (13)0.0657 (13)0.1025 (17)0.0241 (11)0.0046 (12)0.0100 (12)
C490.0499 (11)0.0879 (17)0.113 (2)0.0064 (11)0.0006 (12)0.0179 (15)
C470.0868 (17)0.0775 (16)0.1023 (19)0.0035 (13)0.0287 (15)0.0260 (14)
C340.0930 (17)0.114 (2)0.0592 (13)0.0266 (16)0.0154 (12)0.0115 (14)
C480.0638 (14)0.0815 (16)0.132 (2)0.0167 (12)0.0281 (15)0.0068 (16)
Geometric parameters (Å, º) top
N2—C191.283 (2)C18—H180.9300
N2—C161.4173 (19)C12—C111.382 (2)
O1—C251.355 (2)C12—H120.9300
O1—H10.8200C2—C31.385 (3)
C35—C341.366 (4)C2—H2A0.9300
C35—C361.368 (4)C11—C101.376 (3)
C35—H350.9300C11—H110.9300
N4—C441.279 (2)C14—H140.9300
N4—C411.415 (2)C6—C51.384 (3)
N1—C131.4115 (19)C6—H60.9300
N1—C11.421 (2)C44—H440.9300
N1—C71.427 (2)C41—C421.384 (3)
O2—C501.342 (2)C50—C491.390 (3)
O2—H20.8200C9—C101.371 (3)
N3—C381.415 (2)C9—H90.9300
N3—C261.418 (2)C27—C281.377 (3)
N3—C321.424 (2)C27—H270.9300
C16—C171.387 (2)C43—C421.376 (3)
C16—C151.388 (2)C43—H430.9300
C13—C181.389 (2)C31—C301.380 (3)
C13—C141.393 (2)C31—H310.9300
C20—C211.393 (2)C30—C291.371 (3)
C20—C251.399 (2)C30—H300.9300
C20—C191.447 (2)C28—C291.371 (3)
C7—C121.380 (2)C28—H280.9300
C7—C81.383 (2)C46—C471.374 (3)
C19—H190.9300C46—H460.9300
C1—C61.381 (2)C29—H290.9300
C1—C21.385 (2)C3—C41.361 (3)
C32—C331.378 (3)C3—H30.9300
C32—C371.380 (3)C22—C231.372 (3)
C45—C461.400 (3)C22—H220.9300
C45—C501.402 (3)C42—H420.9300
C45—C441.450 (2)C24—C231.377 (3)
C15—C141.377 (2)C24—H240.9300
C15—H150.9300C10—H100.9300
C39—C401.381 (2)C23—H230.9300
C39—C381.392 (2)C37—C361.391 (3)
C39—H390.9300C37—H370.9300
C26—C271.381 (2)C33—C341.390 (3)
C26—C311.394 (2)C33—H330.9300
C8—C91.385 (3)C4—C51.372 (3)
C8—H80.9300C4—H40.9300
C25—C241.387 (2)C36—H360.9300
C21—C221.369 (3)C5—H50.9300
C21—H210.9300C49—C481.367 (4)
C17—C181.379 (2)C49—H490.9300
C17—H170.9300C47—C481.380 (4)
C40—C411.391 (3)C47—H470.9300
C40—H400.9300C34—H340.9300
C38—C431.392 (3)C48—H480.9300
C19—N2—C16121.25 (14)C1—C6—H6120.0
C25—O1—H1109.5C5—C6—H6120.0
C34—C35—C36119.5 (2)N4—C44—C45121.68 (17)
C34—C35—H35120.2N4—C44—H44119.2
C36—C35—H35120.2C45—C44—H44119.2
C44—N4—C41121.57 (16)C42—C41—C40118.26 (15)
C13—N1—C1120.37 (13)C42—C41—N4118.07 (16)
C13—N1—C7119.58 (13)C40—C41—N4123.53 (16)
C1—N1—C7119.90 (13)O2—C50—C49119.3 (2)
C50—O2—H2109.5O2—C50—C45121.35 (16)
C38—N3—C26120.95 (14)C49—C50—C45119.3 (2)
C38—N3—C32120.38 (14)C10—C9—C8120.57 (18)
C26—N3—C32118.64 (13)C10—C9—H9119.7
C17—C16—C15118.26 (14)C8—C9—H9119.7
C17—C16—N2117.98 (14)C28—C27—C26119.87 (18)
C15—C16—N2123.72 (14)C28—C27—H27120.1
C18—C13—C14118.24 (14)C26—C27—H27120.1
C18—C13—N1120.63 (14)C42—C43—C38120.32 (17)
C14—C13—N1121.13 (15)C42—C43—H43119.8
C21—C20—C25118.23 (15)C38—C43—H43119.8
C21—C20—C19120.08 (15)C30—C31—C26119.92 (19)
C25—C20—C19121.68 (15)C30—C31—H31120.0
C12—C7—C8119.53 (15)C26—C31—H31120.0
C12—C7—N1120.49 (15)C29—C30—C31120.57 (19)
C8—C7—N1119.98 (16)C29—C30—H30119.7
N2—C19—C20122.16 (15)C31—C30—H30119.7
N2—C19—H19118.9C29—C28—C27121.1 (2)
C20—C19—H19118.9C29—C28—H28119.5
C6—C1—C2118.92 (16)C27—C28—H28119.5
C6—C1—N1120.64 (16)C47—C46—C45120.9 (2)
C2—C1—N1120.44 (15)C47—C46—H46119.6
C33—C32—C37119.53 (19)C45—C46—H46119.6
C33—C32—N3121.15 (18)C30—C29—C28119.42 (19)
C37—C32—N3119.32 (18)C30—C29—H29120.3
C46—C45—C50119.02 (18)C28—C29—H29120.3
C46—C45—C44119.56 (18)C4—C3—C2120.7 (2)
C50—C45—C44121.42 (17)C4—C3—H3119.6
C14—C15—C16120.79 (15)C2—C3—H3119.6
C14—C15—H15119.6C21—C22—C23119.31 (19)
C16—C15—H15119.6C21—C22—H22120.3
C40—C39—C38120.99 (16)C23—C22—H22120.3
C40—C39—H39119.5C43—C42—C41121.61 (17)
C38—C39—H39119.5C43—C42—H42119.2
C27—C26—C31119.14 (17)C41—C42—H42119.2
C27—C26—N3120.91 (15)C23—C24—C25120.10 (18)
C31—C26—N3119.94 (16)C23—C24—H24119.9
C7—C8—C9119.82 (18)C25—C24—H24119.9
C7—C8—H8120.1C9—C10—C11119.59 (17)
C9—C8—H8120.1C9—C10—H10120.2
O1—C25—C24118.70 (17)C11—C10—H10120.2
O1—C25—C20121.50 (15)C22—C23—C24120.84 (18)
C24—C25—C20119.80 (17)C22—C23—H23119.6
C22—C21—C20121.70 (18)C24—C23—H23119.6
C22—C21—H21119.2C32—C37—C36119.8 (2)
C20—C21—H21119.2C32—C37—H37120.1
C18—C17—C16121.19 (15)C36—C37—H37120.1
C18—C17—H17119.4C32—C33—C34119.9 (2)
C16—C17—H17119.4C32—C33—H33120.1
C39—C40—C41120.48 (17)C34—C33—H33120.1
C39—C40—H40119.8C3—C4—C5119.5 (2)
C41—C40—H40119.8C3—C4—H4120.2
C43—C38—C39118.32 (15)C5—C4—H4120.2
C43—C38—N3120.70 (16)C35—C36—C37120.6 (2)
C39—C38—N3120.98 (16)C35—C36—H36119.7
C17—C18—C13120.57 (15)C37—C36—H36119.7
C17—C18—H18119.7C4—C5—C6120.6 (2)
C13—C18—H18119.7C4—C5—H5119.7
C7—C12—C11120.09 (17)C6—C5—H5119.7
C7—C12—H12120.0C48—C49—C50120.3 (2)
C11—C12—H12120.0C48—C49—H49119.9
C3—C2—C1120.12 (17)C50—C49—H49119.9
C3—C2—H2A119.9C46—C47—C48119.2 (2)
C1—C2—H2A119.9C46—C47—H47120.4
C10—C11—C12120.39 (18)C48—C47—H47120.4
C10—C11—H11119.8C35—C34—C33120.7 (3)
C12—C11—H11119.8C35—C34—H34119.7
C15—C14—C13120.93 (15)C33—C34—H34119.7
C15—C14—H14119.5C49—C48—C47121.4 (2)
C13—C14—H14119.5C49—C48—H48119.3
C1—C6—C5120.06 (19)C47—C48—H48119.3
C19—N2—C16—C17153.60 (16)N1—C13—C14—C15179.37 (16)
C19—N2—C16—C1528.7 (2)C2—C1—C6—C50.3 (3)
C1—N1—C13—C18144.94 (17)N1—C1—C6—C5179.68 (19)
C7—N1—C13—C1839.5 (2)C41—N4—C44—C45176.17 (17)
C1—N1—C13—C1434.5 (3)C46—C45—C44—N4179.45 (19)
C7—N1—C13—C14141.05 (17)C50—C45—C44—N41.4 (3)
C13—N1—C7—C1244.6 (2)C39—C40—C41—C420.5 (3)
C1—N1—C7—C12130.95 (18)C39—C40—C41—N4175.25 (17)
C13—N1—C7—C8135.76 (18)C44—N4—C41—C42154.47 (19)
C1—N1—C7—C848.6 (2)C44—N4—C41—C4029.8 (3)
C16—N2—C19—C20175.25 (15)C46—C45—C50—O2178.58 (19)
C21—C20—C19—N2178.81 (17)C44—C45—C50—O20.6 (3)
C25—C20—C19—N20.3 (3)C46—C45—C50—C490.4 (3)
C13—N1—C1—C6137.97 (18)C44—C45—C50—C49179.59 (19)
C7—N1—C1—C637.6 (2)C7—C8—C9—C100.6 (3)
C13—N1—C1—C242.6 (2)C31—C26—C27—C280.0 (3)
C7—N1—C1—C2141.80 (17)N3—C26—C27—C28178.53 (17)
C38—N3—C32—C3344.7 (3)C39—C38—C43—C421.7 (3)
C26—N3—C32—C33133.12 (19)N3—C38—C43—C42177.35 (18)
C38—N3—C32—C37135.65 (19)C27—C26—C31—C300.1 (3)
C26—N3—C32—C3746.5 (2)N3—C26—C31—C30178.45 (16)
C17—C16—C15—C141.6 (3)C26—C31—C30—C290.1 (3)
N2—C16—C15—C14179.25 (16)C26—C27—C28—C290.1 (3)
C38—N3—C26—C2743.8 (2)C50—C45—C46—C470.4 (3)
C32—N3—C26—C27138.44 (18)C44—C45—C46—C47178.8 (2)
C38—N3—C26—C31137.73 (18)C31—C30—C29—C280.0 (3)
C32—N3—C26—C3140.1 (2)C27—C28—C29—C300.1 (3)
C12—C7—C8—C91.4 (3)C1—C2—C3—C41.4 (3)
N1—C7—C8—C9178.22 (18)C20—C21—C22—C230.2 (3)
C21—C20—C25—O1179.59 (18)C38—C43—C42—C412.1 (3)
C19—C20—C25—O11.8 (3)C40—C41—C42—C430.9 (3)
C21—C20—C25—C240.6 (3)N4—C41—C42—C43176.91 (18)
C19—C20—C25—C24177.94 (18)O1—C25—C24—C23178.9 (2)
C25—C20—C21—C221.2 (3)C20—C25—C24—C230.8 (3)
C19—C20—C21—C22177.42 (18)C8—C9—C10—C110.6 (3)
C15—C16—C17—C180.8 (2)C12—C11—C10—C90.9 (3)
N2—C16—C17—C18178.64 (15)C21—C22—C23—C241.3 (3)
C38—C39—C40—C410.8 (3)C25—C24—C23—C221.8 (4)
C40—C39—C38—C430.3 (3)C33—C32—C37—C360.1 (3)
C40—C39—C38—N3178.76 (17)N3—C32—C37—C36179.76 (18)
C26—N3—C38—C43148.57 (18)C37—C32—C33—C340.4 (3)
C32—N3—C38—C4333.7 (3)N3—C32—C33—C34179.92 (19)
C26—N3—C38—C3932.4 (3)C2—C3—C4—C50.2 (4)
C32—N3—C38—C39145.35 (18)C34—C35—C36—C370.3 (3)
C16—C17—C18—C130.3 (3)C32—C37—C36—C350.0 (3)
C14—C13—C18—C170.6 (3)C3—C4—C5—C61.1 (4)
N1—C13—C18—C17179.89 (16)C1—C6—C5—C41.0 (4)
C8—C7—C12—C111.0 (3)O2—C50—C49—C48178.2 (2)
N1—C7—C12—C11178.60 (16)C45—C50—C49—C480.8 (3)
C6—C1—C2—C31.5 (3)C45—C46—C47—C480.9 (4)
N1—C1—C2—C3179.12 (17)C36—C35—C34—C330.6 (4)
C7—C12—C11—C100.2 (3)C32—C33—C34—C350.7 (4)
C16—C15—C14—C131.2 (3)C50—C49—C48—C470.3 (4)
C18—C13—C14—C150.1 (3)C46—C47—C48—C490.5 (4)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
O1—H1···N20.821.882.609 (2)147
O2—H2···N40.821.862.590 (2)148
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
O1—H1···N20.821.882.609 (2)147
O2—H2···N40.821.862.590 (2)148
 

Acknowledgements

This work was supported by the National Natural Science Foundation of China (grant Nos. 51372003 and 21271004).

References

First citationBruker (2002). SMART and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.  Google Scholar
First citationDamous, M., Dénès, G., Bouacida, S., Hamlaoui, M., Merazig, H. & Daran, J.-C. (2013). Acta Cryst. E69, o1460–o1461.  CSD CrossRef CAS IUCr Journals Google Scholar
First citationSheldrick, G. M. (1996). SADABS. University of Göttingen, Germany.  Google Scholar
First citationSheldrick, G. M. (2008). Acta Cryst. A64, 112–122.  Web of Science CrossRef CAS IUCr Journals Google Scholar
First citationZheng, Y.-F. (2013). Acta Cryst. E69, o1349.  CSD CrossRef IUCr Journals Google Scholar

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