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

Journal logoCRYSTALLOGRAPHIC
COMMUNICATIONS
ISSN: 2056-9890
Volume 71| Part 11| November 2015| Pages o828-o829
https://doi.org/10.1107/S2056989015018472

Crystal structure of 3-meth­­oxy-2-[5-(naphthalen-1-yl)-4,5-di­hydro-1H-pyrazol-3-yl]phenol

Dongsoo Koha*

aDepartment of Applied Chemistry, Dongduk Women's University, Seoul 136-714, Republic of Korea
*Correspondence e-mail: dskoh@dongduk.ac.kr

Edited by H. Stoeckli-Evans, University of Neuchâtel, Switzerland (Received 8 September 2015; accepted 2 October 2015; online 7 October 2015)

In the title compound, C20H18N2O2, the central pyrazoline ring has an envelope conformation with the atom substituted by the naphthalene ring as the flap. It bridges a benzene ring and a naphthalene ring system which are almost normal to one another, making a dihedral angle of 82.03 (6) °. There is an intra­molecular O—H⋯N hydrogen bond forming an S(6) ring motif. In the crystal, mol­ecules are linked by pairs of N—H⋯π inter­actions, forming inversion dimers. There are also C—H⋯π inter­actions present and the dimers are linked via C—H⋯O hydrogen bonds, forming ribbons propagating along the a-axis direction.

CCDC reference: 1429221

Similar articles

1. Related literature

For the biological properties and synthesis of pyrazoline derivatives, see: Viveka et al. (2015[Viveka, S., Dinesha, Shama, P., Nagaraja, G. K., Ballav, S. & Kerkar, S. (2015). Eur. J. Med. Chem. 101, 442-451.]); Neudorfer et al. (2014[Neudorfer, C., Shanab, K., Jurik, A., Schreiber, V., Neudorfer, C., Vraka, C., Schirmer, E., Holzer, W., Ecker, G., Mitterhauser, M., Wadsak, W. & Spreitzer, H. (2014). Bioorg. Med. Chem. Lett. 24, 4490-4495.]); Hwang et al. (2013[Hwang, D., Yoon, H., Ahn, S., Kim, D.-W., Bae, D.-H., Koh, D. & Lim, Y. (2013). Magn. Reson. Chem. 51, 593-599.]); Congiu et al. (2010[Congiu, C., Onnis, V., Vesci, L., Castorina, M. & Pisano, C. (2010). Bioorg. Med. Chem. 18, 6238-6248.]). For the N—H⋯π inter­action, see: Naveen et al. (2015[Naveen, S., Pavithra, G., Abdoh, M., Ajay Kumar, K., Warad, I. & Lokanath, N. K. (2015). Acta Cryst. E71, 763-765.]). For related structures, see: Zhu et al. (2013[Zhu, Y.-Z., Wang, H., Sun, P.-P. & Tian, Y.-P. (2013). Acta Cryst. E69, o1316.]); Patel et al. (2013[Patel, U. H., Gandhi, S. A., Barot, V. M. & Varma, N. V. S. (2013). Acta Cryst. E69, o840.]).

[Scheme 1]

2. Experimental

2.1. Crystal data

  • C20H18N2O2

  • Mr = 318.36

  • Triclinic, [P \overline 1]

  • a = 7.7280 (12) Å

  • b = 8.6933 (14) Å

  • c = 12.721 (2) Å

  • α = 78.507 (4)°

  • β = 73.781 (4)°

  • γ = 76.148 (4)°

  • V = 788.7 (2) Å3

  • Z = 2

  • Mo Kα radiation

  • μ = 0.09 mm−1

  • T = 147 K

  • 0.23 × 0.14 × 0.10 mm

2.2. Data collection

  • Bruker Kappa APEX-DUO CCD diffractometer

  • Absorption correction: multi-scan (SADABS; Bruker, 2012[Bruker (2012). APEX2, SAINT and SADABS, Bruker AXS Inc. Madison, Wisconsin, USA.]) Tmin = 0.980, Tmax = 0.991

  • 6731 measured reflections

  • 3605 independent reflections

  • 2963 reflections with I > 2σ(I)

  • Rint = 0.027

2.3. Refinement

  • R[F2 > 2σ(F2)] = 0.042

  • wR(F2) = 0.119

  • S = 1.06

  • 3605 reflections

  • 226 parameters

  • H atoms treated by a mixture of independent and constrained refinement

  • Δρmax = 0.28 e Å−3

  • Δρmin = −0.26 e Å−3

Table 1
Hydrogen-bond geometry (Å, °)

Cg2 and Cg3 are the centroids of rings C4–C8/C13 and C8–C13, respectively.
D—H⋯A D—H H⋯A D⋯A D—H⋯A
O2—H2O⋯N1 0.87 (2) 1.79 (2) 2.5681 (14) 148.0 (19)
N2—H2N⋯Cg3i 0.88 (2) 2.56 (2) 3.1811 (13) 128.1 (14)
C3—H3A⋯Cg2i 1.00 2.80 3.5306 (15) 130
C12—H12A⋯O2ii 0.95 2.54 3.4488 (17) 161
Symmetry codes: (i) -x+2, -y+1, -z; (ii) x+1, y, z.

Data collection: APEX2 (Bruker, 2012[Bruker (2012). APEX2, SAINT and SADABS, Bruker AXS Inc. Madison, Wisconsin, USA.]); cell refinement: SAINT (Bruker, 2012[Bruker (2012). APEX2, SAINT and SADABS, 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: PLATON (Spek, 2009[Spek, A. L. (2009). Acta Cryst. D65, 148-155.]); software used to prepare material for publication: SHELXTL (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]) and PLATON.

Supporting information

CCDC reference: 1429221

Crystal structure: contains datablocks I, New_Global_Publ_Block. DOI: https://doi.org/10.1107/S2056989015018472/su5207sup1.cif

Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S2056989015018472/su5207Isup2.hkl

Supporting information file. DOI: https://doi.org/10.1107/S2056989015018472/su5207Isup3.cml

checkCIF report


Introduction top

Pyrazolines have been reported to show a wide range of biological activities: They have been reported to be effective as Alzheimer drugs (Neudorfer et al., 2014), and as having anti-inflammatory (Viveka et al., 2015) and anti­tumor properties (Congiu et al., 2010). The title pyrazoline derivative was synthesized in continuation of our research program (Hwang et al. 2013), and we report herein on its crystal structure.

The molecular structure of the title compound is shown in Fig. 1. The central pyrazoline ring (N1/N2/C1—C3) has an envelope conformation with the atom C3 as the flap. The benzene ring (C14—C19) and the naphthalene ring system (C4—C13) are attached to the central pyrazoline ring (N1/N2/C1—C3) at positions C1 and C3, respectively. The benzene and naphthalene ring are almost normal to one another with a dihedral angle of is 82.03 (6) °. The meth­oxy group at the ortho position of the benzene ring is almost coplanar with the ring [C16—C15—O1—C20 = 2.2 (2) °]. The hydroxyl group at the ortho position of the benzene ring makes an intra­molecular O—H···N hydrogen bond to form an S(6) ring motif.

In the crystal, molecules are linked by pairs of N—H···π inter­actions forming inversion dimers (Fig. 2 and Table 1). There are also C—H···π inter­actions present and the dimers are linked via C—H···O hydrogen bonds forming ribbons propagating along the a axis direction. (Table 1).

An example of inter­molecular N—H···π inter­action in pyrazoline system was reported in a recent publication (Naveen et al., 2015). Examples of pyrazoline structures have been also published (Zhu et al., 2013; Patel et al., 2013).

Experimental top

To a solution of 6-meth­oxy-2-hy­droxy­aceto­phenone (10 mmol, 1.66 g) in 40 ml of ethanol was added 1-naphthaldehyde (10 mmol, 1.56 g) and the temperature was adjusted to around 276-277 K in an ice-bath. To the reaction mixture was added 10 ml of 50% (w/v) aqueous KOH solution and the reaction mixture was stirred at room temperature for 24 h. At the end of the reaction, ice water was added to the mixture and it was acidified with 6N HCl (pH = 3-4). The resulting precipitate was filtered and washed with water and ethanol. The crude solid was purified by recrystallization from ethanol to give pure chalcone. Excess hydrazine monohydrate (1 ml of 64-65% solution, 13 mmol) was added to a solution of the chalcone compound (5 mmol, 1.52 g) in 30 ml anhydrous ethanol, and the solution was refluxed at 360 K for 5 h. The reaction mixture was cooled to room temperature to yield a solid that was then filtered. The crude solids were purified by recrystallization from ethanol to afford the title compound as yellow needles (m.p.: 429-430 K; yield: 56%).

Refinement top

Crystal data, data collection and structure refinement details are summarized in Table 2. The NH and OH H atoms were located in a difference Fourier map and freely refined. The C-bound H atoms were fixed geometrically and allowed to ride on their parent atoms: C—H = 0.95 - 1.00 Å with Uiso(H) = 1.5Ueq(C) for methyl H atoms and 1.2Ueq(C) for other H atoms.

Related literature top

For the biological properties and synthesis of pyrazoline derivatives, see: Viveka et al. (2015); Neudorfer et al. (2014); Hwang et al. (2013); Congiu et al. (2010). For the N—H···π interaction, see: Naveen et al. (2015). For related structures, see: Zhu et al. (2013); Patel et al. (2013).

Structure description top

Pyrazolines have been reported to show a wide range of biological activities: They have been reported to be effective as Alzheimer drugs (Neudorfer et al., 2014), and as having anti-inflammatory (Viveka et al., 2015) and anti­tumor properties (Congiu et al., 2010). The title pyrazoline derivative was synthesized in continuation of our research program (Hwang et al. 2013), and we report herein on its crystal structure.

The molecular structure of the title compound is shown in Fig. 1. The central pyrazoline ring (N1/N2/C1—C3) has an envelope conformation with the atom C3 as the flap. The benzene ring (C14—C19) and the naphthalene ring system (C4—C13) are attached to the central pyrazoline ring (N1/N2/C1—C3) at positions C1 and C3, respectively. The benzene and naphthalene ring are almost normal to one another with a dihedral angle of is 82.03 (6) °. The meth­oxy group at the ortho position of the benzene ring is almost coplanar with the ring [C16—C15—O1—C20 = 2.2 (2) °]. The hydroxyl group at the ortho position of the benzene ring makes an intra­molecular O—H···N hydrogen bond to form an S(6) ring motif.

In the crystal, molecules are linked by pairs of N—H···π inter­actions forming inversion dimers (Fig. 2 and Table 1). There are also C—H···π inter­actions present and the dimers are linked via C—H···O hydrogen bonds forming ribbons propagating along the a axis direction. (Table 1).

An example of inter­molecular N—H···π inter­action in pyrazoline system was reported in a recent publication (Naveen et al., 2015). Examples of pyrazoline structures have been also published (Zhu et al., 2013; Patel et al., 2013).

To a solution of 6-meth­oxy-2-hy­droxy­aceto­phenone (10 mmol, 1.66 g) in 40 ml of ethanol was added 1-naphthaldehyde (10 mmol, 1.56 g) and the temperature was adjusted to around 276-277 K in an ice-bath. To the reaction mixture was added 10 ml of 50% (w/v) aqueous KOH solution and the reaction mixture was stirred at room temperature for 24 h. At the end of the reaction, ice water was added to the mixture and it was acidified with 6N HCl (pH = 3-4). The resulting precipitate was filtered and washed with water and ethanol. The crude solid was purified by recrystallization from ethanol to give pure chalcone. Excess hydrazine monohydrate (1 ml of 64-65% solution, 13 mmol) was added to a solution of the chalcone compound (5 mmol, 1.52 g) in 30 ml anhydrous ethanol, and the solution was refluxed at 360 K for 5 h. The reaction mixture was cooled to room temperature to yield a solid that was then filtered. The crude solids were purified by recrystallization from ethanol to afford the title compound as yellow needles (m.p.: 429-430 K; yield: 56%).

For the biological properties and synthesis of pyrazoline derivatives, see: Viveka et al. (2015); Neudorfer et al. (2014); Hwang et al. (2013); Congiu et al. (2010). For the N—H···π interaction, see: Naveen et al. (2015). For related structures, see: Zhu et al. (2013); Patel et al. (2013).

Refinement details top

Crystal data, data collection and structure refinement details are summarized in Table 2. The NH and OH H atoms were located in a difference Fourier map and freely refined. The C-bound H atoms were fixed geometrically and allowed to ride on their parent atoms: C—H = 0.95 - 1.00 Å with Uiso(H) = 1.5Ueq(C) for methyl H atoms and 1.2Ueq(C) for other H atoms.

Computing details top

Data collection: APEX2 (Bruker, 2012); cell refinement: SAINT (Bruker, 2012); data reduction: SAINT (Bruker, 2012); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: PLATON (Spek, 2009); software used to prepare material for publication: SHELXTL (Sheldrick, 2008) and PLATON (Spek, 2009).

Figures top
[Figure 1] Fig. 1. The molecular structure of the title compound, with atom labelling. Displacement ellipsoids are drawn at the 30% probability level. The intramolecular O-H···N hydrogen bond is shown as a dashed line (see Table 1).
[Figure 2] Fig. 2. Part of the crystal structure of the title compound, showing the intramolecular O—H···N hydrogen bond and the intermolecular N—H···π interactions, as dashed lines (see Table 1). H atoms not involved in these interactions have been omitted for clarity.
3-Methoxy-2-(5-(naphthalen-1-yl)-4,5-dihydro-1H-pyrazol-3-yl)phenol top
Crystal data top
C20H18N2O2Z = 2
Mr = 318.36F(000) = 336
Triclinic, P1Dx = 1.341 Mg m−3
Hall symbol: -P 1Mo Kα radiation, λ = 0.71073 Å
a = 7.7280 (12) ÅCell parameters from 2949 reflections
b = 8.6933 (14) Åθ = 2.4–27.5°
c = 12.721 (2) ŵ = 0.09 mm−1
α = 78.507 (4)°T = 147 K
β = 73.781 (4)°Needle, yellow
γ = 76.148 (4)°0.23 × 0.14 × 0.10 mm
V = 788.7 (2) Å3
Data collection top
Bruker Kappa APEX-DUO CCD
diffractometer		3605 independent reflections
Radiation source: fine-focus sealed tube2963 reflections with I > 2σ(I)
Bruker Triumph monochromatorRint = 0.027
φ and ω scansθmax = 27.5°, θmin = 1.7°
Absorption correction: multi-scan
(SADABS; Bruker, 2012)		h = −10→9
Tmin = 0.980, Tmax = 0.991k = −11→10
6731 measured reflectionsl = −16→16
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)] = 0.042Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.119H atoms treated by a mixture of independent and constrained refinement
S = 1.06 w = 1/[σ2(Fo2) + (0.0564P)2 + 0.190P]
where P = (Fo2 + 2Fc2)/3
3605 reflections(Δ/σ)max < 0.001
226 parametersΔρmax = 0.28 e Å−3
0 restraintsΔρmin = −0.26 e Å−3
Crystal data top
C20H18N2O2γ = 76.148 (4)°
Mr = 318.36V = 788.7 (2) Å3
Triclinic, P1Z = 2
a = 7.7280 (12) ÅMo Kα radiation
b = 8.6933 (14) ŵ = 0.09 mm−1
c = 12.721 (2) ÅT = 147 K
α = 78.507 (4)°0.23 × 0.14 × 0.10 mm
β = 73.781 (4)°
Data collection top
Bruker Kappa APEX-DUO CCD
diffractometer		3605 independent reflections
Absorption correction: multi-scan
(SADABS; Bruker, 2012)		2963 reflections with I > 2σ(I)
Tmin = 0.980, Tmax = 0.991Rint = 0.027
6731 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0420 restraints
wR(F2) = 0.119H atoms treated by a mixture of independent and constrained refinement
S = 1.06Δρmax = 0.28 e Å−3
3605 reflectionsΔρmin = −0.26 e Å−3
226 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
O10.59916 (15)0.28958 (14)0.48006 (8)0.0359 (3)
O20.28750 (13)0.15225 (12)0.24649 (8)0.0271 (2)
N10.58945 (14)0.25517 (12)0.16583 (8)0.0194 (2)
N20.75708 (14)0.27317 (13)0.09019 (9)0.0201 (2)
C10.60118 (16)0.26040 (14)0.26482 (10)0.0185 (3)
C20.78599 (16)0.29279 (15)0.26322 (10)0.0206 (3)
H2A0.86800.19420.28810.025*
H2B0.77270.37560.30980.025*
C30.85658 (16)0.35262 (14)0.13973 (10)0.0187 (3)
H3A0.99180.31160.11560.022*
C40.81502 (15)0.53454 (14)0.11606 (10)0.0173 (2)
C50.67014 (16)0.61697 (15)0.07244 (11)0.0207 (3)
H5A0.59460.55890.05500.025*
C60.63041 (17)0.78560 (15)0.05276 (11)0.0236 (3)
H6A0.52910.83950.02240.028*
C70.73662 (17)0.87181 (15)0.07702 (11)0.0223 (3)
H7A0.70900.98540.06350.027*
C80.88810 (16)0.79261 (14)0.12231 (10)0.0182 (3)
C91.00239 (17)0.88065 (15)0.14546 (10)0.0219 (3)
H9A0.97540.99430.13190.026*
C101.15088 (17)0.80452 (16)0.18700 (11)0.0246 (3)
H10A1.22670.86490.20180.029*
C111.19088 (17)0.63583 (16)0.20777 (11)0.0239 (3)
H11A1.29400.58300.23670.029*
C121.08277 (16)0.54708 (15)0.18673 (10)0.0207 (3)
H12A1.11130.43360.20200.025*
C130.92878 (15)0.62248 (14)0.14245 (9)0.0171 (2)
C140.45128 (16)0.22550 (15)0.36055 (10)0.0206 (3)
C150.45112 (18)0.23952 (16)0.46981 (11)0.0260 (3)
C160.3089 (2)0.20441 (19)0.55885 (12)0.0347 (3)
H16A0.31100.21430.63150.042*
C170.1636 (2)0.1547 (2)0.54096 (13)0.0389 (4)
H17A0.06560.13110.60210.047*
C180.1581 (2)0.13886 (19)0.43663 (12)0.0340 (3)
H18A0.05710.10460.42600.041*
C190.30079 (17)0.17304 (16)0.34678 (11)0.0234 (3)
C200.6108 (2)0.3009 (2)0.58802 (13)0.0419 (4)
H20A0.72290.33890.58270.063*
H20B0.61400.19530.63320.063*
H20C0.50340.37640.62240.063*
H2O0.383 (3)0.178 (2)0.1972 (18)0.050 (5)*
H2N0.739 (2)0.318 (2)0.0247 (15)0.032 (4)*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
O10.0432 (6)0.0524 (7)0.0186 (5)−0.0193 (5)−0.0083 (4)−0.0069 (5)
O20.0268 (5)0.0338 (6)0.0235 (5)−0.0144 (4)−0.0055 (4)−0.0010 (4)
N10.0224 (5)0.0184 (5)0.0177 (5)−0.0075 (4)−0.0019 (4)−0.0034 (4)
N20.0237 (5)0.0202 (5)0.0167 (5)−0.0086 (4)−0.0009 (4)−0.0042 (4)
C10.0216 (6)0.0148 (6)0.0192 (6)−0.0041 (4)−0.0047 (5)−0.0027 (5)
C20.0218 (6)0.0197 (6)0.0210 (6)−0.0053 (4)−0.0059 (5)−0.0022 (5)
C30.0186 (5)0.0167 (6)0.0209 (6)−0.0045 (4)−0.0033 (4)−0.0036 (5)
C40.0175 (5)0.0171 (6)0.0160 (6)−0.0046 (4)−0.0003 (4)−0.0033 (4)
C50.0190 (6)0.0210 (6)0.0236 (6)−0.0063 (5)−0.0049 (5)−0.0045 (5)
C60.0209 (6)0.0222 (6)0.0265 (7)−0.0004 (5)−0.0079 (5)−0.0021 (5)
C70.0235 (6)0.0165 (6)0.0250 (7)−0.0019 (5)−0.0044 (5)−0.0033 (5)
C80.0196 (6)0.0183 (6)0.0155 (6)−0.0042 (4)−0.0003 (4)−0.0046 (5)
C90.0260 (6)0.0206 (6)0.0194 (6)−0.0074 (5)−0.0010 (5)−0.0066 (5)
C100.0267 (6)0.0306 (7)0.0213 (6)−0.0126 (5)−0.0041 (5)−0.0089 (5)
C110.0209 (6)0.0321 (7)0.0202 (6)−0.0041 (5)−0.0073 (5)−0.0055 (5)
C120.0213 (6)0.0208 (6)0.0194 (6)−0.0035 (5)−0.0046 (5)−0.0029 (5)
C130.0177 (5)0.0185 (6)0.0142 (6)−0.0039 (4)−0.0013 (4)−0.0032 (4)
C140.0242 (6)0.0177 (6)0.0181 (6)−0.0033 (5)−0.0034 (5)−0.0013 (5)
C150.0306 (7)0.0260 (7)0.0207 (7)−0.0052 (5)−0.0061 (5)−0.0024 (5)
C160.0419 (8)0.0403 (9)0.0171 (7)−0.0072 (6)−0.0017 (6)−0.0017 (6)
C170.0331 (8)0.0492 (10)0.0256 (8)−0.0127 (7)0.0054 (6)0.0028 (7)
C180.0271 (7)0.0419 (9)0.0301 (8)−0.0130 (6)−0.0030 (6)0.0036 (6)
C190.0243 (6)0.0220 (6)0.0217 (7)−0.0047 (5)−0.0049 (5)0.0013 (5)
C200.0533 (10)0.0545 (11)0.0247 (8)−0.0106 (8)−0.0159 (7)−0.0118 (7)
Geometric parameters (Å, º) top
O1—C151.3637 (16)C8—C91.4183 (16)
O1—C201.4253 (17)C8—C131.4223 (17)
O2—C191.3582 (16)C9—C101.3675 (18)
O2—H2O0.87 (2)C9—H9A0.9500
N1—C11.2980 (16)C10—C111.4108 (19)
N1—N21.4032 (14)C10—H10A0.9500
N2—C31.4710 (15)C11—C121.3714 (17)
N2—H2N0.880 (18)C11—H11A0.9500
C1—C141.4662 (17)C12—C131.4201 (16)
C1—C21.5145 (16)C12—H12A0.9500
C2—C31.5387 (17)C14—C191.4109 (18)
C2—H2A0.9900C14—C151.4189 (18)
C2—H2B0.9900C15—C161.383 (2)
C3—C41.5218 (16)C16—C171.383 (2)
C3—H3A1.0000C16—H16A0.9500
C4—C51.3709 (17)C17—C181.375 (2)
C4—C131.4349 (16)C17—H17A0.9500
C5—C61.4097 (18)C18—C191.3885 (19)
C5—H5A0.9500C18—H18A0.9500
C6—C71.3634 (18)C20—H20A0.9800
C6—H6A0.9500C20—H20B0.9800
C7—C81.4174 (17)C20—H20C0.9800
C7—H7A0.9500
C15—O1—C20118.42 (12)C8—C9—H9A119.5
C19—O2—H2O108.3 (13)C9—C10—C11119.64 (11)
C1—N1—N2109.49 (10)C9—C10—H10A120.2
N1—N2—C3108.34 (9)C11—C10—H10A120.2
N1—N2—H2N110.6 (11)C12—C11—C10120.83 (11)
C3—N2—H2N116.6 (11)C12—C11—H11A119.6
N1—C1—C14120.08 (11)C10—C11—H11A119.6
N1—C1—C2111.19 (10)C11—C12—C13120.89 (12)
C14—C1—C2128.58 (11)C11—C12—H12A119.6
C1—C2—C3101.19 (9)C13—C12—H12A119.6
C1—C2—H2A111.5C12—C13—C8118.13 (11)
C3—C2—H2A111.5C12—C13—C4122.86 (11)
C1—C2—H2B111.5C8—C13—C4119.00 (10)
C3—C2—H2B111.5C19—C14—C15117.14 (11)
H2A—C2—H2B109.3C19—C14—C1120.32 (11)
N2—C3—C4114.54 (10)C15—C14—C1122.53 (11)
N2—C3—C2100.63 (9)O1—C15—C16123.05 (12)
C4—C3—C2111.44 (10)O1—C15—C14115.53 (11)
N2—C3—H3A110.0C16—C15—C14121.42 (13)
C4—C3—H3A110.0C15—C16—C17119.26 (13)
C2—C3—H3A110.0C15—C16—H16A120.4
C5—C4—C13119.03 (11)C17—C16—H16A120.4
C5—C4—C3122.04 (10)C18—C17—C16121.39 (13)
C13—C4—C3118.91 (10)C18—C17—H17A119.3
C4—C5—C6121.70 (11)C16—C17—H17A119.3
C4—C5—H5A119.1C17—C18—C19119.76 (14)
C6—C5—H5A119.1C17—C18—H18A120.1
C7—C6—C5120.35 (11)C19—C18—H18A120.1
C7—C6—H6A119.8O2—C19—C18116.51 (12)
C5—C6—H6A119.8O2—C19—C14122.46 (11)
C6—C7—C8120.27 (12)C18—C19—C14121.03 (12)
C6—C7—H7A119.9O1—C20—H20A109.5
C8—C7—H7A119.9O1—C20—H20B109.5
C7—C8—C9120.87 (11)H20A—C20—H20B109.5
C7—C8—C13119.64 (11)O1—C20—H20C109.5
C9—C8—C13119.47 (11)H20A—C20—H20C109.5
C10—C9—C8121.02 (12)H20B—C20—H20C109.5
C10—C9—H9A119.5
C1—N1—N2—C3−22.01 (13)C9—C8—C13—C120.77 (17)
N2—N1—C1—C14−172.78 (10)C7—C8—C13—C40.13 (17)
N2—N1—C1—C23.08 (13)C9—C8—C13—C4−178.41 (10)
N1—C1—C2—C315.56 (13)C5—C4—C13—C12−179.29 (11)
C14—C1—C2—C3−169.03 (11)C3—C4—C13—C122.02 (17)
N1—N2—C3—C4−89.55 (12)C5—C4—C13—C8−0.16 (17)
N1—N2—C3—C230.09 (12)C3—C4—C13—C8−178.84 (10)
C1—C2—C3—N2−26.20 (11)N1—C1—C14—C195.35 (18)
C1—C2—C3—C495.64 (10)C2—C1—C14—C19−169.70 (11)
N2—C3—C4—C512.88 (16)N1—C1—C14—C15−175.78 (11)
C2—C3—C4—C5−100.52 (13)C2—C1—C14—C159.2 (2)
N2—C3—C4—C13−168.47 (10)C20—O1—C15—C162.2 (2)
C2—C3—C4—C1378.13 (13)C20—O1—C15—C14−177.87 (13)
C13—C4—C5—C60.10 (18)C19—C14—C15—O1179.62 (11)
C3—C4—C5—C6178.75 (11)C1—C14—C15—O10.72 (18)
C4—C5—C6—C70.0 (2)C19—C14—C15—C16−0.46 (19)
C5—C6—C7—C80.00 (19)C1—C14—C15—C16−179.36 (13)
C6—C7—C8—C9178.47 (11)O1—C15—C16—C17179.83 (13)
C6—C7—C8—C13−0.06 (18)C14—C15—C16—C17−0.1 (2)
C7—C8—C9—C10−178.63 (12)C15—C16—C17—C180.3 (2)
C13—C8—C9—C10−0.10 (18)C16—C17—C18—C190.0 (2)
C8—C9—C10—C11−0.32 (19)C17—C18—C19—O2178.98 (13)
C9—C10—C11—C120.06 (19)C17—C18—C19—C14−0.6 (2)
C10—C11—C12—C130.63 (19)C15—C14—C19—O2−178.77 (11)
C11—C12—C13—C8−1.03 (18)C1—C14—C19—O20.16 (19)
C11—C12—C13—C4178.11 (11)C15—C14—C19—C180.80 (19)
C7—C8—C13—C12179.31 (11)C1—C14—C19—C18179.73 (12)
Hydrogen-bond geometry (Å, º) top
Cg2 and Cg3 are the centroids of rings C4–C8/C13 and C8–C13, respectively.
D—H···AD—HH···AD···AD—H···A
O2—H2O···N10.87 (2)1.79 (2)2.5681 (14)148.0 (19)
N2—H2N···Cg3i0.88 (2)2.56 (2)3.1811 (13)128.1 (14)
C3—H3A···Cg2i1.002.803.5306 (15)130
C12—H12A···O2ii0.952.543.4488 (17)161
Symmetry codes: (i) −x+2, −y+1, −z; (ii) x+1, y, z.
Hydrogen-bond geometry (Å, º) top
Cg2 and Cg3 are the centroids of rings C4–C8/C13 and C8–C13, respectively.
D—H···AD—HH···AD···AD—H···A
O2—H2O···N10.87 (2)1.79 (2)2.5681 (14)148.0 (19)
N2—H2N···Cg3i0.88 (2)2.56 (2)3.1811 (13)128.1 (14)
C3—H3A···Cg2i1.002.803.5306 (15)130
C12—H12A···O2ii0.952.543.4488 (17)161
Symmetry codes: (i) −x+2, −y+1, −z; (ii) x+1, y, z.
 

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ISSN: 2056-9890
Volume 71| Part 11| November 2015| Pages o828-o829
https://doi.org/10.1107/S2056989015018472
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