4-[(E)-({4-[Bis­(2-hy­droxy­eth­yl)amino]­phen­yl}imino)­meth­yl]phenol

Liu, X.; Yang, B.; Borzov, M.V.

doi:10.1107/S1600536810021926

organic compounds

CRYSTALLOGRAPHIC
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ISSN: 2056-9890

Volume 66| Part 7| July 2010| Page o1646

doi:10.1107/S1600536810021926

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4-[(E)-({4-[Bis(2-hydroxyethyl)amino]phenyl}imino)methyl]phenol

Xiaoju Liu,^a Bingqin Yang ^a ^* and Maxim V. Borzov ^a

^aKey Laboratory of Synthetic and Natural Chemistry of the Ministry of Education, College of Chemistry and Material Science, the North-West University of Xi'an, Taibai Bei Avenue 229, Xi'an 710069, Shaanxi Province, People's Republic of China
^*Correspondence e-mail: yangbq@nwu.edu.cn

(Received 17 May 2010; accepted 8 June 2010; online 16 June 2010)

In the title compound, C₁₇H₂₀N₂O₃, the amino N atom is in a planar environment (sum of angles = 360.0°). All hydroxy H atoms are involved in hydrogen bonding. In the crystal structure, two O—H⋯O and an O—H⋯N_imino hydrogen bond result in the formation of a three-dimensional network. The latter hydrogen bonding causes distortion of the planarity of the 4-HO–C₆H₄–CH=N–C₆H₄– fragment by rotation around the =N—C_Ph bond. The crystal studied was a non-merohedral twin [refined BASF parameter for the major component = 0.5293 (7)].

Related literature

For Schiff bases of the general type p-R′–C₆H₄–CH=N–C₆H₄–R′′-p, see: von König et al. (1982 ); Haldavanekar et al. (2009 ); Ferlin et al. (2004 ); Lewis et al. (2009 ). For the only two structurally characterized compounds of the type with R′′ = N(alkyl)₂, see: Nagao et al. (2002 ); Nakai et al. (1976 ). For the structure of 2,2′-(4-{[(1E)-(4-methoxyphenyl)methylene]amino}phenylimino) bisethanol, see: Liu et al. (2010 ). For the preparation, see: Cho & Park (1997 ); Ferlin et al. (2004); von König et al. (1982). For a description of the Cambridge Structural Database, see: Allen (2002 ).

Experimental

Crystal data

C₁₇H₂₀N₂O₃
M_r = 300.35
Monoclinic, P 2₁ /n
a = 10.1426 (9) Å
b = 9.5192 (9) Å
c = 15.8600 (14) Å
β = 92.679 (1)°
V = 1529.6 (2) Å³
Z = 4
Mo Kα radiation
μ = 0.09 mm⁻¹
T = 296 K
0.36 × 0.27 × 0.13 mm

Data collection

Bruker SMART APEXII diffractometer
Absorption correction: multi-scan (TWINABS; Sheldrick, 1996 ) T_min = 0.968, T_max = 0.988
5506 measured reflections
5506 independent reflections
2959 reflections with I > 2σ(I)

Refinement

R[F² > 2σ(F²)] = 0.047
wR(F²) = 0.109
S = 0.84
5506 reflections
217 parameters
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.16 e Å⁻³
Δρ_min = −0.18 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O1—H1⋯O3ⁱ	0.89 (2)	1.82 (2)	2.669 (2)	160 (2)
O2—H2⋯N1ⁱⁱ	0.95 (2)	1.82 (2)	2.771 (2)	172 (2)
O3—H3⋯O2ⁱⁱⁱ	0.89 (2)	1.79 (2)	2.674 (2)	174 (2)
Symmetry codes: (i) x, y, z+1; (ii) $[x-{\script{1\over 2}}, -y+{\script{1\over 2}}, z-{\script{1\over 2}}]$ ; (iii) $[-x+{\script{3\over 2}}, y+{\script{1\over 2}}, -z+{\script{1\over 2}}]$ .

Data collection: APEX2 (Bruker, 2007 ); cell refinement: SAINT (Bruker, 2007); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008) and OLEX2 (Dolomanov et al., 2009 ); software used to prepare material for publication: SHELXL97 and OLEX2.

Supporting information

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536810021926/hg2687sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536810021926/hg2687Isup2.hkl

checkCIF report

Comment top

Schiff bases of general type p-R'–C₆H₄–CH=N–C₆H₄–R"-p are well-known objects that find their practical application in various areas [photography (for instance, see von König et al., 1982), medicinal and pharmaceutical chemistry (for instance, see Haldavanekar et al., 2009; Ferlin et al., 2004; Lewis et al., 2009)]. Recently we were interested in preparation of a series of 2,2'-(4-{[(1E)-phenylmethylene]amino}phenylimino)bisethanols as semi-products for their further conversion into paracyclophanes. This way, 4-[(E)-({4-[bis(2-hydroxyethyl)amino]phenyl}imino)methyl]phenol, C₁₇H₂₀N₂O₃, (I), and 2,2'-(4-{[(1E)-(4-methoxyphenyl)methylene]amino}phenylimino)bisethanol, C₁₈H₂₂N₂O₃, [II; Liu et al. (2010)], were prepared by a condensation reaction between 2,2'-[(4-aminophenyl)imino]bisethanol and 4-methoxy- or 4-hydroxybenzaldehyde, respectively (see Scheme).

Despite of the fact that structurally characterized Schiff bases of general type p-R'–C₆H₄–CH=N–C₆H₄–R"-p are well presented in the Cambridge Structural Database [CSD; Version 5.27, release February 2009; Allen, 2002; 128 entries, 173 fragments], among them there are only two compounds with R" = N(alkyl)₂ [namely: R' = H, R'' = NEt₂ (Nagao et al., 2002) and R' = NO₂, R" = NMe₂ (Nakai et al., 1976)]. From this viewpoint, X-ray single crystal study of (I) presents a certain descriptive interest.

The asymmetric unit of (I) is shown in Fig. 1. Except of dihedral angle C7–N1–C8–C9, asymmetric units of (I) and [II; Liu et al. (2010)] have nearly identical geometries (Supplementary materials). Bond lengths, valency angles and C4–C7–N1–C8 torsion angle values for C4/C7/N1/C8 fragment match well the reported median values for p-R'–C₆H₄–CH=N–C₆H₄–R"-p [analysis of the Cambridge Structural Database (CSD); Version 5.27, release February 2009; Allen, 2002; 128 entries, 173 fragments]. Fragments O1/C1—C7/N1 and C8—C13/N2/C14/C16 are nearly planar [within 0.04 and 0.07 Å for (I)]. Atom N2 is also in a planar environment [sum of the valent angles 360.0 (6)°] what presents the most frequent case for aryldialkylamines (range from 317.6 to 360.0°, median value 359.0°)..

All hydroxy H-atoms in (I) are involved into hydrogen bonding [for the H-bonds lengths and angles values see the Table 1]. This way, O1—H1···O3 H-bonds assemble the molecules in chains stretched along the c-axis of the crystal lattice [linked molecules are connected by a simple (0,0,±1) translation]. These chains, in their turn, assemble into "foldered" zigzag layers parallel to the a0b face due to O2—H2···N1 bonds (see Fig. 2). Finally, O3—H3···O2 bonds join the adjacent layers what completes the entire 3D-framework (see Fig. 3). Involving of the N1 imino-atom into H-binding, evidently, causes a considerable distortion of the 4-HO–C₆H₄–CH=N–C₆H₄– fragment planarity by rotation around the ═N—C_Ph bond.

Related literature top

For Schiff bases of general type p-R'–C₆H₄–CH=N–C₆H₄–R"-p in various areas, see, for instance: von König et al. (1982); Haldavanekar et al. (2009); Ferlin et al. (2004); Lewis et al. (2009). For the only two structurally characterized compounds of the type with R" = N(alkyl)₂, see: Nagao et al. (2002); Nakai et al. (1976). For the structure of 2,2'-(4-{[(1E)-(4-methoxyphenyl)methylene]amino}phenylimino) bisethanol, see: Liu et al. (2010). For a description of preparation routines, see: Cho & Park (1997); Ferlin et al. (2004); von König et al. (1982). For a description of the Cambridge Structural Database, see: Allen (2002).

Experimental top

1-Chloro-4-nitrobenzene, 4-methoxy- and 4-hydroxybenzaldehydes, 2,2'-iminobisethanol, ammonium formate, 10% Pd/C catalyst and solvents were purchased from Sinopharm Chemical Reagent and Tianjin Fuyu Chemical companies. 2,2'-[(4-nitrophenyl)imino]bisethanol was prepared as described by Cho & Park (1997) and Ferlin et al. (2004). Reduction of the nitro-group was carried out as described by Lewis et al. (2009). Schiff-base preparation was done closely to what described by von König et al. (1982). – ¹H NMR spectra were recorded on a Varian INOVA-400 instrument in CD₃OD at 298 K using the resonance of the residual solvent protons as an internal reference [δ(H) = 3.30 ppm]. Procedure: 1-chloro-4-nitrobenzene (15.76 g, 0.10 mol) was dissolved in 2,2'-iminobisethanol (50 ml). The reaction mixture was heated at 393 K for 10 h, cooled down to room temperature, the precipitated crude 2,2'-[(4-nitrophenyl)imino]bisethanol filtered off, dried in vacuum and recrystallized from minimal amount of hot ethanol. Yield 11.54 g (51%). 2,2'-[(4-nitrophenyl)imino]bisethanol (8.15 g, 0.036 mol) was dissolved in MeOH (50 ml). To this solution, HCOONH₄(0.216 mol) and 10% Pd/C (0.6 g) were added and the slurry was stirred at 293 K for 30 min. On removal of the catalyst by filtration, the filtrate was placed into a N₂-flushed flask containing 1 ml of acetic acid and an equimolar (0.036 mol) amount of 4-hydroxybenzaldehyde (0.036 mol) was added dropwise at 333 K during 30 min. The reaction mixture was kept at the same temperature for additional 30 min, cooled down to 273 K and ice-cold water (200 ml) was added. The precipitated light-green (I) solid was collected by filtration, washed with water, dried under reduced pressure and, finally, re-crystallized by a slow evaporation of their methanol solutions in air at 293 K. Yield 92%, m.p. 476 K. ¹H NMR for (I) δ: 8.45 (s, 1H, CH═N), 6.78–7.73 (m, 8H, C₆H₄), 3.30, 3.74 (both t, 4 H and 4 H, ³J_HH = 7.2 Hz, CH₂). Single crystal of (I) suitable for X-ray diffraction analysis was picked up directly from the obtained materials.

Computing details top

Data collection: APEX2 (Bruker, 2007); cell refinement: SAINT (Bruker, 2007); data reduction: SAINT (Bruker, 2007); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008) and OLEX2 (Dolomanov et al., 2009); software used to prepare material for publication: SHELXL97 (Sheldrick, 2008) and OLEX2 (Dolomanov et al., 2009).

Figures top

	Fig. 1. Asymmetric unit of the compound (I) with labelling and thermal ellipsoids at the 50% probability level.
	Fig. 2. Assembling of the molecules of (I) into a "foldered" zigzag layer. Hydrogen atoms except of the OH ones are omitted for clarity. Labelling is provided only for atoms involved in H-bonding. H-bonds are depicted as dashed lines.
	Fig. 3. Inter-layer assembling of the molecules of (I) into a 3D-network. Hydrogen atoms except of the OH ones are omitted for clarity. Only O3—H3···O2ⁱⁱⁱ [symmetry code: (iii) –x + 1.5, y + 0.5, –z + 0.5] bonds and their symmetry equivalents are depicted (dashed lines).

4-[(E)-({4-[bis(2-hydroxyethyl)amino]phenyl}imino)methyl]phenol top

Crystal data top

C₁₇H₂₀N₂O₃	F(000) = 640
M_r = 300.35	D_x = 1.304 Mg m⁻³
Monoclinic, P2₁/n	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2yn	Cell parameters from 4620 reflections
a = 10.1426 (9) Å	θ = 2.3–27.0°
b = 9.5192 (9) Å	µ = 0.09 mm⁻¹
c = 15.8600 (14) Å	T = 296 K
β = 92.679 (1)°	Block, green
V = 1529.6 (2) Å³	0.36 × 0.27 × 0.13 mm
Z = 4

Data collection top

Bruker SMART APEXII diffractometer	5506 measured reflections
Radiation source: fine-focus sealed tube	5506 independent reflections
Graphite monochromator	2959 reflections with I > 2σ(I)
Detector resolution: 8.333 pixels mm^-1	θ_max = 25.1°, θ_min = 2.3°
phi and ω scans	h = −12→12
Absorption correction: multi-scan (TWINABS; Sheldrick, 1996)	k = 0→11
T_min = 0.968, T_max = 0.988	l = 0→18

Refinement top

Refinement on F²	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F² > 2σ(F²)] = 0.047	H atoms treated by a mixture of independent and constrained refinement
wR(F²) = 0.109	w = 1/[σ²(F_o²) + (0.0702P)²] where P = (F_o² + 2F_c²)/3
S = 0.84	(Δ/σ)_max < 0.001
5506 reflections	Δρ_max = 0.16 e Å⁻³
217 parameters	Δρ_min = −0.18 e Å⁻³
0 restraints	Extinction correction: SHELXL97 (Sheldrick, 2008), Fc^*=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.0107 (15)

Crystal data top

C₁₇H₂₀N₂O₃	V = 1529.6 (2) Å³
M_r = 300.35	Z = 4
Monoclinic, P2₁/n	Mo Kα radiation
a = 10.1426 (9) Å	µ = 0.09 mm⁻¹
b = 9.5192 (9) Å	T = 296 K
c = 15.8600 (14) Å	0.36 × 0.27 × 0.13 mm
β = 92.679 (1)°

Data collection top

Bruker SMART APEXII diffractometer	5506 measured reflections
Absorption correction: multi-scan (TWINABS; Sheldrick, 1996)	5506 independent reflections
T_min = 0.968, T_max = 0.988	2959 reflections with I > 2σ(I)

Refinement top

R[F² > 2σ(F²)] = 0.047	0 restraints
wR(F²) = 0.109	H atoms treated by a mixture of independent and constrained refinement
S = 0.84	Δρ_max = 0.16 e Å⁻³
5506 reflections	Δρ_min = −0.18 e Å⁻³
217 parameters

Special details top

Experimental. Sample of (I) was a two-component non-merohedral twin with approximately equal component contribution. Thus, the structure of (I) was solved and pre-refined for one of the components (HKLF 4 format) and finally refined for the full set of reflexions (HKLF 5 file format). The refined BASF parameter for the prevailing component equals 0.5293 (7).

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.

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 > 2σ(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	0.84481 (15)	0.10572 (15)	1.16972 (7)	0.0735 (5)
O2	0.56639 (11)	0.06213 (12)	0.32409 (7)	0.0477 (3)
O3	0.90811 (13)	0.32742 (15)	0.26638 (8)	0.0649 (4)
N1	0.89456 (12)	0.22592 (15)	0.77116 (8)	0.0438 (4)
N2	0.89798 (12)	0.13765 (13)	0.41928 (7)	0.0423 (4)
C1	0.84745 (17)	0.11819 (19)	1.08463 (10)	0.0479 (5)
C2	0.80262 (17)	0.00647 (18)	1.03658 (10)	0.0551 (5)
H2A	0.7703	−0.0730	1.0628	0.066*
C3	0.80526 (16)	0.01135 (18)	0.94979 (10)	0.0505 (5)
H3A	0.7768	−0.0661	0.9181	0.061*
C4	0.84966 (15)	0.12981 (17)	0.90899 (9)	0.0394 (4)
C5	0.89081 (15)	0.24390 (17)	0.95828 (9)	0.0434 (4)
H5	0.9183	0.3256	0.9322	0.052*
C6	0.89162 (15)	0.23798 (17)	1.04515 (9)	0.0443 (4)
H6	0.9218	0.3143	1.0772	0.053*
C7	0.85321 (16)	0.1266 (2)	0.81716 (10)	0.0442 (4)
C8	0.88878 (15)	0.20652 (16)	0.68171 (9)	0.0401 (4)
C9	0.78712 (16)	0.13679 (17)	0.63799 (9)	0.0444 (4)
H9	0.7167	0.1025	0.6673	0.053*
C10	0.78819 (16)	0.11715 (17)	0.55179 (9)	0.0452 (4)
H10	0.7175	0.0715	0.5242	0.054*
C11	0.89302 (15)	0.16422 (16)	0.50488 (9)	0.0385 (4)
C12	0.99168 (16)	0.24157 (17)	0.54925 (9)	0.0449 (4)
H12	1.0603	0.2802	0.5201	0.054*
C13	0.98867 (16)	0.26125 (17)	0.63517 (9)	0.0450 (4)
H13	1.0557	0.3128	0.6627	0.054*
C14	0.79307 (15)	0.05868 (17)	0.37522 (9)	0.0433 (4)
H14B	0.7674	−0.0192	0.4103	0.052*
H14A	0.8258	0.0202	0.3236	0.052*
C15	0.67400 (15)	0.14873 (17)	0.35403 (10)	0.0442 (4)
H15B	0.6494	0.1998	0.4038	0.053*
H15A	0.6948	0.2166	0.3110	0.053*
C16	1.01067 (15)	0.17981 (18)	0.37224 (10)	0.0479 (5)
H16A	1.0211	0.1130	0.3269	0.057*
H16B	1.0892	0.1743	0.4094	0.057*
C17	1.00283 (17)	0.32486 (19)	0.33494 (10)	0.0536 (5)
H17A	0.9782	0.3916	0.3777	0.064*
H17B	1.0885	0.3519	0.3155	0.064*
H1	0.880 (2)	0.183 (2)	1.1930 (13)	0.107 (9)*
H2	0.5011 (18)	0.130 (2)	0.3071 (11)	0.086 (7)*
H3	0.913 (2)	0.408 (2)	0.2387 (13)	0.117 (9)*
H7	0.8211 (14)	0.0378 (16)	0.7921 (9)	0.050 (5)*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
O1	0.1199 (13)	0.0705 (11)	0.0296 (8)	−0.0099 (9)	−0.0027 (7)	0.0057 (7)
O2	0.0524 (8)	0.0448 (8)	0.0442 (7)	0.0026 (7)	−0.0141 (6)	−0.0081 (6)
O3	0.0834 (10)	0.0586 (9)	0.0499 (8)	−0.0142 (8)	−0.0269 (7)	0.0155 (7)
N1	0.0480 (9)	0.0525 (10)	0.0303 (8)	−0.0016 (7)	−0.0057 (6)	0.0003 (7)
N2	0.0449 (8)	0.0523 (9)	0.0290 (8)	−0.0043 (7)	−0.0030 (7)	0.0018 (6)
C1	0.0604 (12)	0.0515 (12)	0.0314 (10)	0.0057 (10)	−0.0029 (9)	0.0022 (8)
C2	0.0775 (13)	0.0447 (12)	0.0430 (11)	−0.0039 (10)	0.0006 (10)	0.0081 (9)
C3	0.0674 (13)	0.0429 (11)	0.0406 (11)	−0.0041 (9)	−0.0050 (9)	−0.0011 (8)
C4	0.0432 (10)	0.0426 (10)	0.0319 (9)	0.0031 (8)	−0.0042 (8)	0.0015 (8)
C5	0.0492 (11)	0.0445 (11)	0.0365 (10)	−0.0023 (9)	0.0010 (8)	0.0039 (8)
C6	0.0508 (11)	0.0455 (11)	0.0364 (10)	−0.0008 (9)	−0.0017 (8)	−0.0056 (8)
C7	0.0466 (11)	0.0480 (12)	0.0373 (11)	0.0008 (9)	−0.0057 (8)	−0.0017 (9)
C8	0.0452 (10)	0.0437 (10)	0.0307 (9)	0.0000 (8)	−0.0061 (8)	0.0004 (8)
C9	0.0448 (10)	0.0548 (11)	0.0333 (10)	−0.0069 (9)	−0.0025 (8)	0.0042 (8)
C10	0.0473 (10)	0.0521 (11)	0.0352 (10)	−0.0096 (9)	−0.0087 (8)	0.0014 (8)
C11	0.0440 (10)	0.0404 (10)	0.0303 (9)	0.0020 (8)	−0.0073 (8)	0.0050 (7)
C12	0.0445 (10)	0.0555 (12)	0.0343 (10)	−0.0052 (9)	−0.0036 (8)	0.0060 (8)
C13	0.0456 (10)	0.0515 (12)	0.0370 (10)	−0.0068 (9)	−0.0092 (8)	0.0010 (8)
C14	0.0521 (10)	0.0451 (11)	0.0318 (9)	0.0012 (9)	−0.0067 (8)	−0.0011 (8)
C15	0.0486 (10)	0.0451 (11)	0.0383 (10)	−0.0015 (9)	−0.0066 (8)	−0.0017 (8)
C16	0.0472 (10)	0.0608 (12)	0.0351 (10)	0.0070 (9)	−0.0035 (8)	0.0014 (8)
C17	0.0553 (11)	0.0654 (13)	0.0392 (10)	−0.0113 (10)	−0.0088 (9)	0.0078 (9)

Geometric parameters (Å, º) top

O1—C1	1.3563 (18)	C7—H7	0.984 (15)
O1—H1	0.89 (2)	C8—C13	1.383 (2)
O2—C15	1.4310 (17)	C8—C9	1.385 (2)
O2—H2	0.952 (19)	C9—C10	1.3805 (19)
O3—C17	1.4172 (18)	C9—H9	0.9300
O3—H3	0.89 (2)	C10—C11	1.400 (2)
N1—C7	1.277 (2)	C10—H10	0.9300
N1—C8	1.4292 (18)	C11—C12	1.405 (2)
N2—C11	1.3843 (18)	C12—C13	1.3773 (19)
N2—C16	1.4504 (18)	C12—H12	0.9300
N2—C14	1.4546 (18)	C13—H13	0.9300
C1—C2	1.373 (2)	C14—C15	1.506 (2)
C1—C6	1.385 (2)	C14—H14B	0.9700
C2—C3	1.379 (2)	C14—H14A	0.9700
C2—H2A	0.9300	C15—H15B	0.9700
C3—C4	1.386 (2)	C15—H15A	0.9700
C3—H3A	0.9300	C16—C17	1.503 (2)
C4—C5	1.391 (2)	C16—H16A	0.9700
C4—C7	1.459 (2)	C16—H16B	0.9700
C5—C6	1.3786 (19)	C17—H17A	0.9700
C5—H5	0.9300	C17—H17B	0.9700
C6—H6	0.9300

C1—O1—H1	108.4 (14)	C9—C10—H10	119.2
C15—O2—H2	102.4 (11)	C11—C10—H10	119.2
C17—O3—H3	110.1 (14)	N2—C11—C10	121.75 (14)
C7—N1—C8	118.17 (14)	N2—C11—C12	121.97 (14)
C11—N2—C16	121.30 (13)	C10—C11—C12	116.28 (14)
C11—N2—C14	120.41 (13)	C13—C12—C11	121.25 (15)
C16—N2—C14	118.18 (12)	C13—C12—H12	119.4
O1—C1—C2	117.58 (16)	C11—C12—H12	119.4
O1—C1—C6	122.93 (16)	C12—C13—C8	121.84 (15)
C2—C1—C6	119.49 (15)	C12—C13—H13	119.1
C1—C2—C3	120.43 (16)	C8—C13—H13	119.1
C1—C2—H2A	119.8	N2—C14—C15	111.96 (13)
C3—C2—H2A	119.8	N2—C14—H14B	109.2
C2—C3—C4	121.04 (16)	C15—C14—H14B	109.2
C2—C3—H3A	119.5	N2—C14—H14A	109.2
C4—C3—H3A	119.5	C15—C14—H14A	109.2
C3—C4—C5	117.93 (14)	H14B—C14—H14A	107.9
C3—C4—C7	118.23 (16)	O2—C15—C14	109.72 (13)
C5—C4—C7	123.83 (15)	O2—C15—H15B	109.7
C6—C5—C4	121.16 (15)	C14—C15—H15B	109.7
C6—C5—H5	119.4	O2—C15—H15A	109.7
C4—C5—H5	119.4	C14—C15—H15A	109.7
C5—C6—C1	119.89 (15)	H15B—C15—H15A	108.2
C5—C6—H6	120.1	N2—C16—C17	115.35 (14)
C1—C6—H6	120.1	N2—C16—H16A	108.4
N1—C7—C4	125.38 (17)	C17—C16—H16A	108.4
N1—C7—H7	121.1 (8)	N2—C16—H16B	108.4
C4—C7—H7	113.5 (8)	C17—C16—H16B	108.4
C13—C8—C9	117.40 (14)	H16A—C16—H16B	107.5
C13—C8—N1	118.95 (14)	O3—C17—C16	109.84 (14)
C9—C8—N1	123.64 (14)	O3—C17—H17A	109.7
C10—C9—C8	121.38 (15)	C16—C17—H17A	109.7
C10—C9—H9	119.3	O3—C17—H17B	109.7
C8—C9—H9	119.3	C16—C17—H17B	109.7
C9—C10—C11	121.62 (15)	H17A—C17—H17B	108.2

O1—C1—C2—C3	−178.64 (16)	C16—N2—C11—C10	−176.39 (14)
C6—C1—C2—C3	2.0 (3)	C14—N2—C11—C10	−0.2 (2)
C1—C2—C3—C4	−1.7 (3)	C16—N2—C11—C12	4.6 (2)
C2—C3—C4—C5	−0.3 (2)	C14—N2—C11—C12	−179.19 (14)
C2—C3—C4—C7	178.38 (16)	C9—C10—C11—N2	176.24 (14)
C3—C4—C5—C6	2.1 (2)	C9—C10—C11—C12	−4.7 (2)
C7—C4—C5—C6	−176.54 (15)	N2—C11—C12—C13	−176.78 (14)
C4—C5—C6—C1	−1.8 (2)	C10—C11—C12—C13	4.1 (2)
O1—C1—C6—C5	−179.58 (16)	C11—C12—C13—C8	−0.2 (2)
C2—C1—C6—C5	−0.3 (2)	C9—C8—C13—C12	−3.3 (2)
C8—N1—C7—C4	−178.79 (15)	N1—C8—C13—C12	177.43 (14)
C3—C4—C7—N1	−178.17 (16)	C11—N2—C14—C15	79.93 (17)
C5—C4—C7—N1	0.5 (3)	C16—N2—C14—C15	−103.73 (15)
C7—N1—C8—C13	−143.95 (16)	N2—C14—C15—O2	−170.21 (11)
C7—N1—C8—C9	36.9 (2)	C11—N2—C16—C17	−89.41 (17)
C13—C8—C9—C10	2.8 (2)	C14—N2—C16—C17	94.28 (17)
N1—C8—C9—C10	−178.01 (14)	N2—C16—C17—O3	−71.61 (18)
C8—C9—C10—C11	1.3 (2)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O1—H1···O3ⁱ	0.89 (2)	1.82 (2)	2.669 (2)	160 (2)
O2—H2···N1ⁱⁱ	0.95 (2)	1.82 (2)	2.771 (2)	172 (2)
O3—H3···O2ⁱⁱⁱ	0.89 (2)	1.79 (2)	2.674 (2)	174 (2)

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

Experimental details

Crystal data
Chemical formula	C₁₇H₂₀N₂O₃
M_r	300.35
Crystal system, space group	Monoclinic, P2₁/n
Temperature (K)	296
a, b, c (Å)	10.1426 (9), 9.5192 (9), 15.8600 (14)
β (°)	92.679 (1)
V (Å³)	1529.6 (2)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.09
Crystal size (mm)	0.36 × 0.27 × 0.13

Data collection
Diffractometer	Bruker SMART APEXII diffractometer
Absorption correction	Multi-scan (TWINABS; Sheldrick, 1996)
T_min, T_max	0.968, 0.988
No. of measured, independent and observed [I > 2σ(I)] reflections	5506, 5506, 2959
R_int	?
(sin θ/λ)_max (Å⁻¹)	0.597

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.047, 0.109, 0.84
No. of reflections	5506
No. of parameters	217
H-atom treatment	H atoms treated by a mixture of independent and constrained refinement
Δρ_max, Δρ_min (e Å⁻³)	0.16, −0.18

Computer programs: APEX2 (Bruker, 2007), SAINT (Bruker, 2007), SHELXS97 (Sheldrick, 2008), SHELXTL (Sheldrick, 2008) and OLEX2 (Dolomanov et al., 2009), SHELXL97 (Sheldrick, 2008) and OLEX2 (Dolomanov et al., 2009).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O1—H1···O3ⁱ	0.89 (2)	1.82 (2)	2.669 (2)	160 (2)
O2—H2···N1ⁱⁱ	0.95 (2)	1.82 (2)	2.771 (2)	172 (2)
O3—H3···O2ⁱⁱⁱ	0.89 (2)	1.79 (2)	2.674 (2)	174 (2)

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

Acknowledgements

Financial support from the National Natural Science Foundation of China (project No. 20972125) is gratefully acknowledged. The authors are grateful to Mr Sun Wei for his help in measuring the ¹H NMR spectra.

References

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