3,5-Diphenyl-1-(quinolin-2-yl)-4,5-dihydro-1H-pyrazol-5-ol

Najib, M.H. bin; Tan, A.L.; Young, D.J.; Ng, S.W.; Tiekink, E.R.T.

doi:10.1107/S1600536812029340

organic compounds

CRYSTALLOGRAPHIC
COMMUNICATIONS

ISSN: 2056-9890

Volume 68| Part 8| August 2012| Pages o2310-o2311

https://doi.org/10.1107/S1600536812029340

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3,5-Diphenyl-1-(quinolin-2-yl)-4,5-dihydro-1H-pyrazol-5-ol

Muhd. Hidayat bin Najib,^a Ai Ling Tan,^a David J. Young,^a ‡ Seik Weng Ng ^b,^c and Edward R. T. Tiekink ^b ^*

^aFaculty of Science, Universiti Brunei Darussalam, Jalan Tungku Link BE 1410, Negara Brunei Darussalam, ^bDepartment of Chemistry, University of Malaya, 50603 Kuala Lumpur, Malaysia, and ^cChemistry Department and Faculty of Science, King Abdulaziz University, PO Box 80203 Jeddah, Saudi Arabia
^*Correspondence e-mail: edward.tiekink@gmail.com

(Received 27 June 2012; accepted 27 June 2012; online 4 July 2012)

In the title compound, C₂₄H₁₉N₃O, the pyrazole ring is close to being planar (r.m.s. deviation of the five fitted atoms = 0.062 Å), and each of the N-bound quinoline ring [dihedral angle = 9.90 (7)°] and the C-bound phenyl ring in the 3-position is close to being coplanar [dihedral angle = 8.87 (9)°]. However, the phenyl ring in the 5-position forms a dihedral angle of 72.31 (9)°. The hydroxy group forms an intramolecular hydrogen bond to the quinoline N atom. In the crystal, molecules are connected into supramolecular layers two molecules thick in the bc plane by C—H⋯O and C—H⋯π interactions.

Related literature

For applications of coordination complexes of hydrazones as organic light emitting diodes and supramolecular magnetic clusters, see: Zhang et al. (2011 , 2012 ). For the synthesis of hydrazones, see: Gupta et al. (2007 ). For background to and the synthesis of the target molecules, see: Najib et al. (2012a ,b ,c )

Experimental

Crystal data

C₂₄H₁₉N₃O
M_r = 365.42
Monoclinic, C 2/c
a = 30.505 (2) Å
b = 7.8881 (4) Å
c = 16.5191 (12) Å
β = 113.718 (9)°
V = 3639.1 (4) Å³
Z = 8
Mo Kα radiation
μ = 0.08 mm⁻¹
T = 100 K
0.35 × 0.30 × 0.25 mm

Data collection

Agilent SuperNova Dual diffractometer with an Atlas detector
Absorption correction: multi-scan (CrysAlis PRO; Agilent, 2012 ) T_min = 0.784, T_max = 1.000
12177 measured reflections
4209 independent reflections
3419 reflections with I > 2σ(I)
R_int = 0.033

Refinement

R[F² > 2σ(F²)] = 0.048
wR(F²) = 0.130
S = 1.07
4209 reflections
257 parameters
1 restraint
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.30 e Å⁻³
Δρ_min = −0.32 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

Cg1 and Cg2 are the centroids of the C1–C6 and N1,C1,C6–C9 rings, respectively.

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O1—H1o⋯N1	0.87 (1)	2.15 (2)	2.8149 (19)	133 (3)
C3—H3⋯O1ⁱ	0.95	2.50	3.298 (2)	142
C11—H11A⋯Cg1ⁱⁱ	0.99	2.92	3.8528 (18)	157
C17—H17⋯Cg2ⁱⁱⁱ	0.95	2.58	3.4426 (18)	151
C24—H24⋯Cg2ⁱⁱ	0.95	2.97	3.6239 (18)	127
Symmetry codes: (i) $[-x+1, y, -z+{\script{3\over 2}}]$ ; (ii) $[-x+{\script{1\over 2}}, y+{\script{3\over 2}}, -z-{\script{1\over 2}}]$ ; (iii) x, y+1, z.

Data collection: CrysAlis PRO (Agilent, 2012); cell refinement: CrysAlis PRO; data reduction: CrysAlis PRO; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997 ) and DIAMOND (Brandenburg, 2006 ); software used to prepare material for publication: publCIF (Westrip, 2010 ).

Supporting information

Crystal structure: contains datablocks global, I. DOI: https://doi.org/10.1107/S1600536812029340/sj5251sup1.cif

Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S1600536812029340/sj5251Isup2.hkl

Supporting information file. DOI: https://doi.org/10.1107/S1600536812029340/sj5251Isup3.cml

checkCIF report

Comment top

We have previously prepared 3,5-dimethyl-1-(2'-quinolyl)-pyrazole (Najib et al., 2012c) and a related Cinchonine derived ligand (Zhang et al., 2011) for the synthesis of photoluminescent zinc (Najib et al., 2012a; Najib et al., 2012b) and iridium complexes (Zhang et al., 2012). These ligands are made by the condensation of the corresponding hydrazine (Najib et al., 2012a) with a β-diketone (Gupta et al., 2007). In our attempted synthesis of 3,5-diphenyl-1-(2'-quinolyl)-pyrazole using the same procedure, we were surprised to prepare the title compound, (I), presumably from initial condensation but only partial dehydration. The reluctance of this benzylic, tertiary alcohol to undergo dehydration may be due to the resulting unfavourable proximity of the phenyl and quinoline groups.

In (I), the pyrazolyl ring has an envelope configuration with the C10 atom being the flap atom. However, the distortion from planarity is relatively minor with the r.m.s. deviation = 0.062 Å and maximum deviations of 0.051 (1) Å for the N1 atom and -0.052 (2) Å for the C10 atom. The N2-bound quinolinyl ring (r.m.s. deviation = 0.009 Å) forms a dihedral angle of 9.90 (7)° with the pyrazolyl plane. The C12-bound phenyl ring is almost co-planar with the pyrazolyl plane [dihedral angle = 8.87 (9)°) whereas the C10-bound phenyl ring forms a dihedral angle of 72.31 (9)°. The latter projects to one side of the pyrazolyl plane and the hydroxy group to the other. The hydroxy group forms an intramolecular hydrogen bond to the quinolinyl-N1 atom, Table 1.

In the crystal packing, C—H···O interactions link molecules into centrosymmetric dimers via 18-membered {···HC₃NCNCO}₂ synthons, Table 1. These are connected into supramolecular layers two molecules thick in the bc plane via C—H···π interactions, Fig. 2 and Table 1. Layers stack along the a axis without specific interactions between them.

Related literature top

For applications of coordination complexes of hydrazones as organic light emitting diodes and supramolecular magnetic clusters, see: Zhang et al. (2011, 2012). For the synthesis of hydrazones, see: Gupta et al. (2007). For background to and the synthesis of the target molecules, see: Najib et al. (2012a,b,c)

Experimental top

Ethanol (25 ml) was added to a mixture of 2-hydrazinylquinoline (0.08 g) and dibenzoylmethane (0.23 g) and the resulting solution was refluxed for 48 h. The solvent was removed to obtain an orange residue that was recrystallized from toluene to yield 0.063 g of orange crystals. A second recrystallization from toluene produced 0.035 g (19.1%) of orange crystals. Melting point: 503 K. IR ν/cm^-1: 3409, 3061, 3028, 1616, 1602, 1559, 1507, 1480, 1447, 1432, 1405, 1371, 1343, 1326, 1302, 1263, 1248, 1233, 1170, 1149, 1070, 1050, 856, 828, 756, 698, 692. ¹H NMR 400 MHz (CDCl₃) δ: 8.00 (1H, d), 7.80 (3H, m), 7.58 (3H, m), 7.42 (5H, m), 7.30 (1H, m), 7.21 (2H, m), 7.15(1H, m), 3.83 (1H, d), 3.50 (1H, d), 1.25 (1H, s).

Structure description top

For applications of coordination complexes of hydrazones as organic light emitting diodes and supramolecular magnetic clusters, see: Zhang et al. (2011, 2012). For the synthesis of hydrazones, see: Gupta et al. (2007). For background to and the synthesis of the target molecules, see: Najib et al. (2012a,b,c)

Computing details top

Data collection: CrysAlis PRO (Agilent, 2012); cell refinement: CrysAlis PRO (Agilent, 2012); data reduction: CrysAlis PRO (Agilent, 2012); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997) and DIAMOND (Brandenburg, 2006); software used to prepare material for publication: publCIF (Westrip, 2010).

Figures top

	Fig. 1. The molecular structure of (I) showing the atom-labelling scheme and displacement ellipsoids at the 50% probability level.
	Fig. 2. A view of the supramolecular array in the bc plane in (I). The C—H···O and C—H···π interactions are shown as orange and purple dashed lines, respectively.
	Fig. 3. A view of the unit-cell contents of (I) in projection down the b axis. The C—H···O and C—H···π interactions are shown as orange and purple dashed lines, respectively.

3,5-Diphenyl-1-(quinolin-2-yl)-4,5-dihydro-1H-pyrazol-5-ol top

Crystal data top

C₂₄H₁₉N₃O	F(000) = 1536
M_r = 365.42	D_x = 1.334 Mg m⁻³
Monoclinic, C2/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -C 2yc	Cell parameters from 4159 reflections
a = 30.505 (2) Å	θ = 2.4–27.5°
b = 7.8881 (4) Å	µ = 0.08 mm⁻¹
c = 16.5191 (12) Å	T = 100 K
β = 113.718 (9)°	Block, yellow
V = 3639.1 (4) Å³	0.35 × 0.30 × 0.25 mm
Z = 8

Data collection top

Agilent SuperNova Dual diffractometer with an Atlas detector	4209 independent reflections
Radiation source: fine-focus sealed tube	3419 reflections with I > 2σ(I)
Mirror monochromator	R_int = 0.033
Detector resolution: 10.4041 pixels mm^-1	θ_max = 27.6°, θ_min = 2.5°
ω scan	h = −30→39
Absorption correction: multi-scan (CrysAlis PRO; Agilent, 2012)	k = −9→10
T_min = 0.784, T_max = 1.000	l = −21→14
12177 measured reflections

Refinement top

Refinement on F²	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F² > 2σ(F²)] = 0.048	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.130	H atoms treated by a mixture of independent and constrained refinement
S = 1.07	w = 1/[σ²(F_o²) + (0.0534P)² + 3.4025P] where P = (F_o² + 2F_c²)/3
4209 reflections	(Δ/σ)_max < 0.001
257 parameters	Δρ_max = 0.30 e Å⁻³
1 restraint	Δρ_min = −0.32 e Å⁻³

Crystal data top

C₂₄H₁₉N₃O	V = 3639.1 (4) Å³
M_r = 365.42	Z = 8
Monoclinic, C2/c	Mo Kα radiation
a = 30.505 (2) Å	µ = 0.08 mm⁻¹
b = 7.8881 (4) Å	T = 100 K
c = 16.5191 (12) Å	0.35 × 0.30 × 0.25 mm
β = 113.718 (9)°

Data collection top

Agilent SuperNova Dual diffractometer with an Atlas detector	4209 independent reflections
Absorption correction: multi-scan (CrysAlis PRO; Agilent, 2012)	3419 reflections with I > 2σ(I)
T_min = 0.784, T_max = 1.000	R_int = 0.033
12177 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.048	1 restraint
wR(F²) = 0.130	H atoms treated by a mixture of independent and constrained refinement
S = 1.07	Δρ_max = 0.30 e Å⁻³
4209 reflections	Δρ_min = −0.32 e Å⁻³
257 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

	x	y	z	U_iso*/U_eq
O1	0.43944 (4)	0.27304 (15)	0.51758 (8)	0.0265 (3)
H1o	0.4449 (11)	0.250 (4)	0.5723 (9)	0.087 (11)*
N1	0.40135 (5)	0.26810 (16)	0.64704 (9)	0.0201 (3)
N2	0.36017 (5)	0.33420 (17)	0.50098 (9)	0.0208 (3)
N3	0.32336 (5)	0.29868 (16)	0.42006 (9)	0.0210 (3)
C1	0.40233 (6)	0.20442 (18)	0.72467 (10)	0.0187 (3)
C2	0.44529 (6)	0.2169 (2)	0.80119 (11)	0.0225 (3)
H2	0.4724	0.2708	0.7980	0.027*
C3	0.44810 (6)	0.1519 (2)	0.88010 (11)	0.0241 (4)
H3	0.4772	0.1607	0.9311	0.029*
C4	0.40834 (6)	0.0723 (2)	0.88630 (11)	0.0246 (4)
H4	0.4107	0.0275	0.9413	0.030*
C5	0.36626 (6)	0.05912 (19)	0.81328 (11)	0.0232 (3)
H5	0.3395	0.0054	0.8179	0.028*
C6	0.36217 (6)	0.12429 (18)	0.73125 (10)	0.0195 (3)
C7	0.31958 (6)	0.1126 (2)	0.65227 (11)	0.0218 (3)
H7	0.2921	0.0580	0.6534	0.026*
C8	0.31823 (6)	0.17893 (19)	0.57593 (11)	0.0213 (3)
H8	0.2899	0.1730	0.5232	0.026*
C9	0.36047 (6)	0.25830 (19)	0.57660 (10)	0.0193 (3)
C10	0.40389 (6)	0.3997 (2)	0.49355 (11)	0.0215 (3)
C11	0.38509 (6)	0.4283 (2)	0.39280 (10)	0.0234 (4)
H11A	0.3836	0.5507	0.3786	0.028*
H11B	0.4056	0.3703	0.3677	0.028*
C12	0.33582 (5)	0.35170 (19)	0.35852 (10)	0.0196 (3)
C13	0.42182 (5)	0.56032 (19)	0.54739 (10)	0.0185 (3)
C14	0.47014 (6)	0.6033 (2)	0.57873 (11)	0.0228 (3)
H14	0.4921	0.5291	0.5690	0.027*
C15	0.48632 (6)	0.7545 (2)	0.62411 (12)	0.0275 (4)
H15	0.5192	0.7839	0.6449	0.033*
C16	0.45464 (6)	0.8621 (2)	0.63909 (11)	0.0273 (4)
H16	0.4658	0.9649	0.6706	0.033*
C17	0.40668 (6)	0.8200 (2)	0.60811 (12)	0.0283 (4)
H17	0.3848	0.8937	0.6184	0.034*
C18	0.39055 (6)	0.6704 (2)	0.56208 (11)	0.0245 (4)
H18	0.3575	0.6429	0.5402	0.029*
C19	0.30291 (5)	0.33954 (19)	0.26559 (10)	0.0194 (3)
C20	0.25909 (6)	0.2537 (2)	0.24096 (11)	0.0213 (3)
H20	0.2515	0.1979	0.2846	0.026*
C21	0.22711 (6)	0.2503 (2)	0.15352 (11)	0.0233 (3)
H21	0.1975	0.1919	0.1372	0.028*
C22	0.23785 (6)	0.3313 (2)	0.08928 (11)	0.0240 (3)
H22	0.2154	0.3305	0.0294	0.029*
C23	0.28120 (6)	0.4133 (2)	0.11249 (11)	0.0238 (4)
H23	0.2887	0.4674	0.0682	0.029*
C24	0.31400 (6)	0.4175 (2)	0.20006 (11)	0.0223 (3)
H24	0.3439	0.4731	0.2154	0.027*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
O1	0.0252 (6)	0.0256 (6)	0.0271 (7)	0.0021 (5)	0.0087 (5)	−0.0023 (5)
N1	0.0211 (7)	0.0193 (6)	0.0190 (7)	−0.0010 (5)	0.0071 (5)	−0.0013 (5)
N2	0.0180 (6)	0.0245 (7)	0.0171 (6)	−0.0051 (5)	0.0042 (5)	−0.0010 (5)
N3	0.0198 (7)	0.0213 (7)	0.0175 (7)	−0.0006 (5)	0.0031 (5)	−0.0006 (5)
C1	0.0216 (8)	0.0162 (7)	0.0194 (8)	0.0011 (6)	0.0094 (6)	−0.0018 (6)
C2	0.0209 (8)	0.0239 (8)	0.0231 (8)	−0.0005 (6)	0.0094 (6)	−0.0018 (6)
C3	0.0253 (8)	0.0263 (8)	0.0188 (8)	0.0043 (6)	0.0068 (6)	−0.0015 (6)
C4	0.0344 (9)	0.0197 (8)	0.0218 (8)	0.0042 (6)	0.0134 (7)	0.0031 (6)
C5	0.0286 (8)	0.0165 (7)	0.0272 (8)	−0.0003 (6)	0.0140 (7)	0.0001 (6)
C6	0.0229 (8)	0.0140 (7)	0.0232 (8)	0.0012 (6)	0.0108 (6)	−0.0015 (6)
C7	0.0221 (8)	0.0187 (7)	0.0273 (8)	−0.0026 (6)	0.0128 (7)	−0.0016 (6)
C8	0.0189 (7)	0.0198 (7)	0.0233 (8)	−0.0015 (6)	0.0066 (6)	−0.0020 (6)
C9	0.0214 (8)	0.0170 (7)	0.0194 (8)	0.0003 (6)	0.0083 (6)	−0.0009 (6)
C10	0.0210 (8)	0.0222 (8)	0.0217 (8)	−0.0031 (6)	0.0088 (6)	−0.0024 (6)
C11	0.0227 (8)	0.0258 (8)	0.0197 (8)	−0.0047 (6)	0.0065 (6)	−0.0027 (6)
C12	0.0205 (8)	0.0173 (7)	0.0202 (8)	0.0012 (6)	0.0074 (6)	−0.0004 (6)
C13	0.0210 (7)	0.0196 (7)	0.0146 (7)	−0.0023 (6)	0.0067 (6)	0.0003 (6)
C14	0.0199 (8)	0.0245 (8)	0.0239 (8)	−0.0003 (6)	0.0085 (6)	−0.0036 (6)
C15	0.0212 (8)	0.0278 (9)	0.0292 (9)	−0.0051 (7)	0.0057 (7)	−0.0041 (7)
C16	0.0335 (9)	0.0216 (8)	0.0233 (8)	−0.0019 (7)	0.0077 (7)	−0.0040 (6)
C17	0.0310 (9)	0.0256 (9)	0.0308 (9)	0.0052 (7)	0.0150 (7)	−0.0023 (7)
C18	0.0200 (8)	0.0264 (8)	0.0273 (9)	0.0005 (6)	0.0096 (7)	0.0010 (7)
C19	0.0193 (7)	0.0180 (7)	0.0186 (7)	0.0039 (6)	0.0051 (6)	−0.0017 (6)
C20	0.0214 (8)	0.0220 (8)	0.0202 (8)	0.0001 (6)	0.0081 (6)	−0.0006 (6)
C21	0.0182 (8)	0.0256 (8)	0.0245 (8)	−0.0021 (6)	0.0069 (6)	−0.0015 (6)
C22	0.0229 (8)	0.0256 (8)	0.0198 (8)	0.0010 (6)	0.0048 (6)	−0.0010 (6)
C23	0.0260 (8)	0.0249 (8)	0.0207 (8)	−0.0015 (6)	0.0097 (7)	0.0012 (6)
C24	0.0201 (8)	0.0218 (8)	0.0246 (8)	−0.0019 (6)	0.0086 (6)	−0.0020 (6)

Geometric parameters (Å, º) top

O1—C10	1.409 (2)	C11—H11A	0.9900
O1—H1o	0.871 (10)	C11—H11B	0.9900
N1—C9	1.3220 (19)	C12—C19	1.461 (2)
N1—C1	1.366 (2)	C13—C18	1.382 (2)
N2—C9	1.382 (2)	C13—C14	1.393 (2)
N2—N3	1.3850 (17)	C14—C15	1.389 (2)
N2—C10	1.481 (2)	C14—H14	0.9500
N3—C12	1.290 (2)	C15—C16	1.381 (2)
C1—C2	1.411 (2)	C15—H15	0.9500
C1—C6	1.421 (2)	C16—C17	1.382 (2)
C2—C3	1.371 (2)	C16—H16	0.9500
C2—H2	0.9500	C17—C18	1.383 (2)
C3—C4	1.405 (2)	C17—H17	0.9500
C3—H3	0.9500	C18—H18	0.9500
C4—C5	1.367 (2)	C19—C24	1.400 (2)
C4—H4	0.9500	C19—C20	1.405 (2)
C5—C6	1.407 (2)	C20—C21	1.380 (2)
C5—H5	0.9500	C20—H20	0.9500
C6—C7	1.426 (2)	C21—C22	1.386 (2)
C7—C8	1.350 (2)	C21—H21	0.9500
C7—H7	0.9500	C22—C23	1.381 (2)
C8—C9	1.429 (2)	C22—H22	0.9500
C8—H8	0.9500	C23—C24	1.389 (2)
C10—C13	1.518 (2)	C23—H23	0.9500
C10—C11	1.543 (2)	C24—H24	0.9500
C11—C12	1.503 (2)

C10—O1—H1o	104 (2)	C12—C11—H11B	111.1
C9—N1—C1	117.48 (13)	C10—C11—H11B	111.1
C9—N2—N3	119.53 (12)	H11A—C11—H11B	109.1
C9—N2—C10	123.18 (12)	N3—C12—C19	120.74 (14)
N3—N2—C10	113.46 (12)	N3—C12—C11	113.60 (14)
C12—N3—N2	108.27 (13)	C19—C12—C11	125.63 (14)
N1—C1—C2	118.47 (14)	C18—C13—C14	118.91 (14)
N1—C1—C6	122.77 (14)	C18—C13—C10	121.07 (14)
C2—C1—C6	118.76 (14)	C14—C13—C10	119.93 (14)
C3—C2—C1	120.37 (15)	C15—C14—C13	120.18 (15)
C3—C2—H2	119.8	C15—C14—H14	119.9
C1—C2—H2	119.8	C13—C14—H14	119.9
C2—C3—C4	120.71 (15)	C16—C15—C14	120.13 (16)
C2—C3—H3	119.6	C16—C15—H15	119.9
C4—C3—H3	119.6	C14—C15—H15	119.9
C5—C4—C3	120.08 (15)	C15—C16—C17	119.90 (16)
C5—C4—H4	120.0	C15—C16—H16	120.1
C3—C4—H4	120.0	C17—C16—H16	120.1
C4—C5—C6	120.68 (16)	C16—C17—C18	119.89 (16)
C4—C5—H5	119.7	C16—C17—H17	120.1
C6—C5—H5	119.7	C18—C17—H17	120.1
C5—C6—C1	119.40 (14)	C13—C18—C17	120.99 (15)
C5—C6—C7	123.54 (15)	C13—C18—H18	119.5
C1—C6—C7	117.06 (14)	C17—C18—H18	119.5
C8—C7—C6	120.24 (15)	C24—C19—C20	119.05 (14)
C8—C7—H7	119.9	C24—C19—C12	120.41 (14)
C6—C7—H7	119.9	C20—C19—C12	120.51 (15)
C7—C8—C9	118.28 (14)	C21—C20—C19	120.14 (15)
C7—C8—H8	120.9	C21—C20—H20	119.9
C9—C8—H8	120.9	C19—C20—H20	119.9
N1—C9—N2	115.56 (14)	C20—C21—C22	120.45 (15)
N1—C9—C8	124.12 (14)	C20—C21—H21	119.8
N2—C9—C8	120.31 (14)	C22—C21—H21	119.8
O1—C10—N2	110.25 (13)	C23—C22—C21	119.90 (15)
O1—C10—C13	111.82 (12)	C23—C22—H22	120.1
N2—C10—C13	111.52 (13)	C21—C22—H22	120.1
O1—C10—C11	108.52 (13)	C22—C23—C24	120.55 (16)
N2—C10—C11	100.60 (12)	C22—C23—H23	119.7
C13—C10—C11	113.56 (13)	C24—C23—H23	119.7
C12—C11—C10	103.23 (13)	C23—C24—C19	119.88 (15)
C12—C11—H11A	111.1	C23—C24—H24	120.1
C10—C11—H11A	111.1	C19—C24—H24	120.1

C9—N2—N3—C12	−165.92 (14)	N2—C10—C11—C12	−7.55 (15)
C10—N2—N3—C12	−7.26 (17)	C13—C10—C11—C12	−126.82 (14)
C9—N1—C1—C2	−178.59 (14)	N2—N3—C12—C19	−176.76 (13)
C9—N1—C1—C6	2.3 (2)	N2—N3—C12—C11	1.48 (18)
N1—C1—C2—C3	−178.78 (14)	C10—C11—C12—N3	4.29 (18)
C6—C1—C2—C3	0.4 (2)	C10—C11—C12—C19	−177.58 (14)
C1—C2—C3—C4	−0.2 (2)	O1—C10—C13—C18	−153.52 (15)
C2—C3—C4—C5	−0.1 (2)	N2—C10—C13—C18	−29.6 (2)
C3—C4—C5—C6	0.2 (2)	C11—C10—C13—C18	83.26 (19)
C4—C5—C6—C1	0.0 (2)	O1—C10—C13—C14	30.0 (2)
C4—C5—C6—C7	179.05 (15)	N2—C10—C13—C14	153.99 (14)
N1—C1—C6—C5	178.84 (14)	C11—C10—C13—C14	−93.20 (18)
C2—C1—C6—C5	−0.3 (2)	C18—C13—C14—C15	0.1 (2)
N1—C1—C6—C7	−0.3 (2)	C10—C13—C14—C15	176.68 (15)
C2—C1—C6—C7	−179.38 (14)	C13—C14—C15—C16	0.6 (3)
C5—C6—C7—C8	179.68 (15)	C14—C15—C16—C17	−0.6 (3)
C1—C6—C7—C8	−1.3 (2)	C15—C16—C17—C18	−0.1 (3)
C6—C7—C8—C9	0.7 (2)	C14—C13—C18—C17	−0.9 (2)
C1—N1—C9—N2	175.86 (13)	C10—C13—C18—C17	−177.38 (15)
C1—N1—C9—C8	−2.9 (2)	C16—C17—C18—C13	0.9 (3)
N3—N2—C9—N1	165.54 (13)	N3—C12—C19—C24	171.36 (14)
C10—N2—C9—N1	9.0 (2)	C11—C12—C19—C24	−6.6 (2)
N3—N2—C9—C8	−15.6 (2)	N3—C12—C19—C20	−6.8 (2)
C10—N2—C9—C8	−172.13 (14)	C11—C12—C19—C20	175.19 (15)
C7—C8—C9—N1	1.5 (2)	C24—C19—C20—C21	−1.5 (2)
C7—C8—C9—N2	−177.26 (14)	C12—C19—C20—C21	176.65 (15)
C9—N2—C10—O1	52.69 (19)	C19—C20—C21—C22	0.0 (2)
N3—N2—C10—O1	−105.08 (14)	C20—C21—C22—C23	1.3 (3)
C9—N2—C10—C13	−72.15 (18)	C21—C22—C23—C24	−0.9 (3)
N3—N2—C10—C13	130.07 (13)	C22—C23—C24—C19	−0.7 (2)
C9—N2—C10—C11	167.12 (14)	C20—C19—C24—C23	1.9 (2)
N3—N2—C10—C11	9.34 (16)	C12—C19—C24—C23	−176.29 (14)
O1—C10—C11—C12	108.17 (14)

Hydrogen-bond geometry (Å, º) top

Cg1 and Cg2 are the centroids of the C1–C6 and N1,C1,C6–C9 rings, respectively.

D—H···A	D—H	H···A	D···A	D—H···A
O1—H1o···N1	0.87 (1)	2.15 (2)	2.8149 (19)	133 (3)
C3—H3···O1ⁱ	0.95	2.50	3.298 (2)	142
C11—H11A···Cg1ⁱⁱ	0.99	2.92	3.8528 (18)	157
C17—H17···Cg2ⁱⁱⁱ	0.95	2.58	3.4426 (18)	151
C24—H24···Cg2ⁱⁱ	0.95	2.97	3.6239 (18)	127

Symmetry codes: (i) −x+1, y, −z+3/2; (ii) −x+1/2, y+3/2, −z−1/2; (iii) x, y+1, z.

Experimental details

Crystal data
Chemical formula	C₂₄H₁₉N₃O
M_r	365.42
Crystal system, space group	Monoclinic, C2/c
Temperature (K)	100
a, b, c (Å)	30.505 (2), 7.8881 (4), 16.5191 (12)
β (°)	113.718 (9)
V (Å³)	3639.1 (4)
Z	8
Radiation type	Mo Kα
µ (mm⁻¹)	0.08
Crystal size (mm)	0.35 × 0.30 × 0.25

Data collection
Diffractometer	Agilent SuperNova Dual diffractometer with an Atlas detector
Absorption correction	Multi-scan (CrysAlis PRO; Agilent, 2012)
T_min, T_max	0.784, 1.000
No. of measured, independent and observed [I > 2σ(I)] reflections	12177, 4209, 3419
R_int	0.033
(sin θ/λ)_max (Å⁻¹)	0.651

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.048, 0.130, 1.07
No. of reflections	4209
No. of parameters	257
No. of restraints	1
H-atom treatment	H atoms treated by a mixture of independent and constrained refinement
Δρ_max, Δρ_min (e Å⁻³)	0.30, −0.32

Computer programs: CrysAlis PRO (Agilent, 2012), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), ORTEP-3 for Windows (Farrugia, 1997) and DIAMOND (Brandenburg, 2006), publCIF (Westrip, 2010).

Hydrogen-bond geometry (Å, º) top

Cg1 and Cg2 are the centroids of the C1–C6 and N1,C1,C6–C9 rings, respectively.

D—H···A	D—H	H···A	D···A	D—H···A
O1—H1o···N1	0.871 (10)	2.15 (2)	2.8149 (19)	133 (3)
C3—H3···O1ⁱ	0.95	2.50	3.298 (2)	142
C11—H11A···Cg1ⁱⁱ	0.99	2.92	3.8528 (18)	157
C17—H17···Cg2ⁱⁱⁱ	0.95	2.58	3.4426 (18)	151
C24—H24···Cg2ⁱⁱ	0.95	2.97	3.6239 (18)	127

Symmetry codes: (i) −x+1, y, −z+3/2; (ii) −x+1/2, y+3/2, −z−1/2; (iii) x, y+1, z.

Footnotes

‡Additional correspondence author, e-mail: david.young@ubd.edu.bn.

Acknowledgements

We gratefully acknowledge funding from the Brunei Research Council, and thank the Ministry of Higher Education (Malaysia) for funding structural studies through the High-Impact Research scheme (UM.C/HIR/MOHE/SC/12).

References

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Volume 68| Part 8| August 2012| Pages o2310-o2311

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