Opipramol

Fun, H.-K.; Loh, W.-S.; Siddegowda, M.S.; Yathirajan, H.S.; Narayana, B.

doi:10.1107/S1600536811021131

organic compounds

CRYSTALLOGRAPHIC
COMMUNICATIONS

ISSN: 2056-9890

Volume 67| Part 7| July 2011| Page o1598

doi:10.1107/S1600536811021131

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Opipramol

Hoong-Kun Fun,^a ^*‡ Wan-Sin Loh,^a § M. S. Siddegowda,^b H. S. Yathirajan ^b and B. Narayana ^c

^aX-ray Crystallography Unit, School of Physics, Universiti Sains Malaysia, 11800 USM, Penang, Malaysia, ^bDepartment of Studies in Chemistry, University of Mysore, Manasagangotri, Mysore 570 006, India, and ^cDepartment of Studies in Chemistry, Mangalore University, Mangalagangotri 574 199, India
^*Correspondence e-mail: hkfun@usm.my

(Received 31 May 2011; accepted 1 June 2011; online 11 June 2011)

In the title compound (systematic name: 2-{4-[3-(5H-dibenz[b,f]azepin-5-yl)propyl]piperazin-1-yl}ethanol), C₂₃H₂₉N₃O, the 5H-dibenz[b,f]azepine and piperazine rings adopt boat and chair conformations, respectively, and the overall shape of the fused ring part of the molecule is a butterfly. In the crystal, O—H⋯N and C—H⋯O hydrogen bonds link the molecules into a layer parallel to the bc plane.

Related literature

For the application of opipramol, see: Moller et al. (2001 ). For related structures, see: Jasinski et al. (2010 ); Nagaraj et al. (2005 ). For ring conformations, see: Cremer & Pople (1975 ). For bond-length data, see: Allen et al. (1987 ). For the stability of the temperature controller used for the data collection, see: Cosier & Glazer (1986 ).

Experimental

Crystal data

C₂₃H₂₉N₃O
M_r = 363.49
Monoclinic, P 2₁ /c
a = 12.6215 (2) Å
b = 10.5929 (2) Å
c = 14.3629 (2) Å
β = 90.966 (1)°
V = 1920.02 (5) Å³
Z = 4
Mo Kα radiation
μ = 0.08 mm⁻¹
T = 100 K
0.59 × 0.36 × 0.30 mm

Data collection

Bruker SMART APEXII CCD area-detector diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2009 ) T_min = 0.955, T_max = 0.977
30830 measured reflections
7949 independent reflections
6682 reflections with I > 2σ(I)
R_int = 0.026

Refinement

R[F² > 2σ(F²)] = 0.042
wR(F²) = 0.117
S = 1.03
7949 reflections
248 parameters
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.56 e Å⁻³
Δρ_min = −0.25 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O1—H1O1⋯N2ⁱ	0.896 (16)	1.999 (16)	2.8822 (9)	168.3 (14)
C5—H5A⋯O1ⁱⁱ	0.95	2.41	3.3478 (11)	167
Symmetry codes: (i) $[x, -y+{\script{5\over 2}}, z+{\script{1\over 2}}]$ ; (ii) $[x, -y+{\script{3\over 2}}, z-{\script{1\over 2}}]$ .

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

Supporting information

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536811021131/is2726sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536811021131/is2726Isup2.hkl

Supporting information file. DOI: 10.1107/S1600536811021131/is2726Isup3.cml

checkCIF report

Comment top

Opipramol [systematic IUPAC name: 4-[3-(5H-dibenz[b,f] azepin-5-yl)propyl]-1-piperazinethanol] is an antidepressant and anxiolytic typically used in the treatment of generalized anxiety disorder (Moller et al., 2001). Opipramol is a tricyclic compound with no reuptake-inhibiting properties. However, it has pronounced D2-, 5-HT2-, and H1-blocking potential and high affinity to sigma receptors (sigma-1 and sigma-2). The crystal structure studies of opipramol dipicrate is reported (Jasinski et al., 2010). In view of the importance of the title compound, C₂₃H₂₉N₃O, the crystal structure is reported.

In the title compound (Fig. 1), the seven-membered, 5H-dibenz[b,f]azepine ring (N1/C1/C6–C9/C14) adopts a boat conformation (Cremer & Pople, 1975) and the overall molecular shape is that of a butterfly (Nagaraj et al., 2005) whereas the piperazine ring (N2/C18/C19/N3/C20/C21) adopts a chair conformation (Cremer & Pople, 1975) with the puckering parameters, Q = 0.5934 (8) Å, Θ = 177.94 (8)°, ϕ = 305.8 (18)°. The torsion angle between the 5H-dibenz[b,f]azepine and the piperazine rings, N1–C15–C16–C17 is 61.73 (8)°. Bond lengths (Allen et al., 1987) and angles are within the normal ranges.

In the crystal packing (Fig. 2), intermolecular O1—H1O1···N2 and C5—H5A···O1 hydrogen bonds link the molecules into layers parallel to the bc plane.

Related literature top

For the application of opipramol, see: Moller et al. (2001). For related structures, see: Jasinski et al. (2010); Nagaraj et al. (2005). For ring conformations, see: Cremer & Pople (1975). For bond-length data, see: Allen et al. (1987). For the stability of the temperature controller used for the data collection, see: Cosier & Glazer (1986).

Experimental top

The title compound was obtained as a gift sample from R. L. Fine Chem. Ltd., Bangalore, India. The compound was recrystallized from acetone (m. p. 373–374 K).

Computing details top

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

Figures top

	Fig. 1. The molecular structure of the title compound, showing 50% probability displacement ellipsoids and the atom-numbering scheme.
	Fig. 2. The crystal packing of the title compound, viewed along the b axis. H atoms not involved in the intermolecular interactions (dashed lines) have been omitted for clarity.

2-{4-[3-(5H-dibenz[b,f]azepin-5- yl)propyl]piperazin-1-yl}ethanol top

Crystal data top

C₂₃H₂₉N₃O	F(000) = 784
M_r = 363.49	D_x = 1.257 Mg m⁻³
Monoclinic, P2₁/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 9885 reflections
a = 12.6215 (2) Å	θ = 2.9–34.2°
b = 10.5929 (2) Å	µ = 0.08 mm⁻¹
c = 14.3629 (2) Å	T = 100 K
β = 90.966 (1)°	Block, colourless
V = 1920.02 (5) Å³	0.59 × 0.36 × 0.30 mm
Z = 4

Data collection top

Bruker SMART APEXII CCD area-detector diffractometer	7949 independent reflections
Radiation source: fine-focus sealed tube	6682 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.026
ϕ and ω scans	θ_max = 34.3°, θ_min = 2.4°
Absorption correction: multi-scan (SADABS; Bruker, 2009)	h = −16→19
T_min = 0.955, T_max = 0.977	k = −13→16
30830 measured reflections	l = −22→20

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)] = 0.042	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.117	H atoms treated by a mixture of independent and constrained refinement
S = 1.03	w = 1/[σ²(F_o²) + (0.0611P)² + 0.4097P] where P = (F_o² + 2F_c²)/3
7949 reflections	(Δ/σ)_max = 0.001
248 parameters	Δρ_max = 0.56 e Å⁻³
0 restraints	Δρ_min = −0.25 e Å⁻³

Crystal data top

C₂₃H₂₉N₃O	V = 1920.02 (5) Å³
M_r = 363.49	Z = 4
Monoclinic, P2₁/c	Mo Kα radiation
a = 12.6215 (2) Å	µ = 0.08 mm⁻¹
b = 10.5929 (2) Å	T = 100 K
c = 14.3629 (2) Å	0.59 × 0.36 × 0.30 mm
β = 90.966 (1)°

Data collection top

Bruker SMART APEXII CCD area-detector diffractometer	7949 independent reflections
Absorption correction: multi-scan (SADABS; Bruker, 2009)	6682 reflections with I > 2σ(I)
T_min = 0.955, T_max = 0.977	R_int = 0.026
30830 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.042	0 restraints
wR(F²) = 0.117	H atoms treated by a mixture of independent and constrained refinement
S = 1.03	Δρ_max = 0.56 e Å⁻³
7949 reflections	Δρ_min = −0.25 e Å⁻³
248 parameters

Special details top

Experimental. The crystal was placed in the cold stream of an Oxford Cryosystems Cobra open-flow nitrogen cryostat (Cosier & Glazer, 1986) operating at 100.0 (1) K.

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	0.10636 (5)	1.33255 (6)	1.06904 (4)	0.01965 (12)
N1	0.33738 (5)	0.74218 (6)	0.57588 (4)	0.01418 (11)
N2	0.21096 (5)	1.06560 (6)	0.73239 (4)	0.01326 (11)
N3	0.12890 (5)	1.23458 (6)	0.87387 (4)	0.01380 (11)
C1	0.35654 (6)	0.60944 (7)	0.58110 (5)	0.01411 (12)
C2	0.45637 (6)	0.56231 (8)	0.60674 (5)	0.01763 (13)
H2A	0.5136	0.6192	0.6165	0.021*
C3	0.47316 (7)	0.43319 (8)	0.61812 (5)	0.02086 (15)
H3A	0.5412	0.4027	0.6363	0.025*
C4	0.39006 (8)	0.34908 (8)	0.60285 (6)	0.02318 (16)
H4A	0.4011	0.2610	0.6106	0.028*
C5	0.29077 (7)	0.39456 (8)	0.57628 (6)	0.02090 (15)
H5A	0.2344	0.3367	0.5656	0.025*
C6	0.27213 (6)	0.52452 (7)	0.56485 (5)	0.01608 (13)
C7	0.16454 (6)	0.56539 (8)	0.53991 (5)	0.01885 (14)
H7A	0.1084	0.5136	0.5611	0.023*
C8	0.13636 (6)	0.66812 (8)	0.49038 (5)	0.01869 (14)
H8A	0.0627	0.6846	0.4831	0.022*
C9	0.20930 (6)	0.75680 (7)	0.44664 (5)	0.01590 (13)
C10	0.17851 (7)	0.81058 (8)	0.36112 (5)	0.02081 (15)
H10A	0.1099	0.7931	0.3362	0.025*
C11	0.24589 (8)	0.88867 (8)	0.31209 (5)	0.02329 (16)
H11A	0.2239	0.9232	0.2539	0.028*
C12	0.34570 (7)	0.91589 (8)	0.34884 (6)	0.02238 (16)
H12A	0.3926	0.9685	0.3153	0.027*
C13	0.37721 (6)	0.86616 (8)	0.43480 (5)	0.01829 (14)
H13A	0.4454	0.8858	0.4597	0.022*
C14	0.30944 (6)	0.78756 (7)	0.48477 (5)	0.01414 (12)
C15	0.40721 (6)	0.82280 (7)	0.63287 (5)	0.01655 (13)
H15A	0.4750	0.8347	0.6004	0.020*
H15B	0.4229	0.7799	0.6928	0.020*
C16	0.35831 (6)	0.95205 (7)	0.65234 (5)	0.01594 (13)
H16A	0.4100	1.0040	0.6881	0.019*
H16B	0.3434	0.9954	0.5925	0.019*
C17	0.25587 (6)	0.94200 (7)	0.70697 (5)	0.01620 (13)
H17A	0.2028	0.8949	0.6691	0.019*
H17B	0.2700	0.8929	0.7645	0.019*
C18	0.10673 (6)	1.04721 (7)	0.77555 (5)	0.01661 (13)
H18A	0.1148	0.9920	0.8308	0.020*
H18B	0.0580	1.0051	0.7307	0.020*
C19	0.06022 (6)	1.17294 (8)	0.80442 (5)	0.01601 (13)
H19A	0.0522	1.2281	0.7491	0.019*
H19B	−0.0109	1.1594	0.8307	0.019*
C20	0.23213 (6)	1.25503 (7)	0.83151 (5)	0.01593 (13)
H20A	0.2805	1.2962	0.8772	0.019*
H20B	0.2237	1.3121	0.7773	0.019*
C21	0.28023 (6)	1.13121 (7)	0.80016 (5)	0.01553 (13)
H21A	0.3497	1.1479	0.7716	0.019*
H21B	0.2924	1.0762	0.8550	0.019*
C22	0.08179 (6)	1.35398 (7)	0.90363 (5)	0.01556 (13)
H22A	0.0054	1.3403	0.9144	0.019*
H22B	0.0881	1.4162	0.8526	0.019*
C23	0.13187 (6)	1.40919 (7)	0.99127 (5)	0.01650 (13)
H23A	0.2097	1.4132	0.9847	0.020*
H23B	0.1053	1.4960	1.0010	0.020*
H1O1	0.1474 (12)	1.3609 (15)	1.1160 (11)	0.047 (4)*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
O1	0.0255 (3)	0.0212 (3)	0.0123 (2)	−0.0037 (2)	−0.0003 (2)	−0.00024 (19)
N1	0.0171 (3)	0.0124 (3)	0.0129 (2)	0.0007 (2)	−0.00349 (19)	−0.00178 (19)
N2	0.0140 (2)	0.0135 (3)	0.0123 (2)	−0.0022 (2)	−0.00079 (19)	−0.00190 (19)
N3	0.0138 (2)	0.0157 (3)	0.0119 (2)	−0.0006 (2)	−0.00102 (19)	−0.00231 (19)
C1	0.0180 (3)	0.0130 (3)	0.0113 (3)	0.0014 (2)	−0.0002 (2)	−0.0009 (2)
C2	0.0203 (3)	0.0175 (3)	0.0150 (3)	0.0033 (3)	−0.0019 (2)	−0.0009 (2)
C3	0.0276 (4)	0.0191 (3)	0.0159 (3)	0.0078 (3)	−0.0006 (3)	0.0010 (2)
C4	0.0352 (4)	0.0149 (3)	0.0196 (3)	0.0043 (3)	0.0037 (3)	0.0018 (3)
C5	0.0289 (4)	0.0155 (3)	0.0183 (3)	−0.0023 (3)	0.0036 (3)	−0.0002 (3)
C6	0.0199 (3)	0.0153 (3)	0.0131 (3)	−0.0010 (2)	0.0018 (2)	−0.0017 (2)
C7	0.0178 (3)	0.0205 (4)	0.0184 (3)	−0.0035 (3)	0.0021 (2)	−0.0039 (3)
C8	0.0157 (3)	0.0219 (4)	0.0184 (3)	0.0004 (3)	−0.0010 (2)	−0.0059 (3)
C9	0.0172 (3)	0.0165 (3)	0.0139 (3)	0.0036 (2)	−0.0019 (2)	−0.0036 (2)
C10	0.0251 (4)	0.0211 (4)	0.0160 (3)	0.0063 (3)	−0.0062 (3)	−0.0038 (3)
C11	0.0349 (4)	0.0213 (4)	0.0136 (3)	0.0087 (3)	−0.0013 (3)	−0.0003 (3)
C12	0.0306 (4)	0.0196 (4)	0.0171 (3)	0.0047 (3)	0.0058 (3)	0.0021 (3)
C13	0.0194 (3)	0.0177 (3)	0.0177 (3)	0.0023 (3)	0.0023 (2)	−0.0002 (2)
C14	0.0163 (3)	0.0136 (3)	0.0125 (3)	0.0029 (2)	−0.0007 (2)	−0.0020 (2)
C15	0.0172 (3)	0.0151 (3)	0.0172 (3)	0.0009 (2)	−0.0041 (2)	−0.0034 (2)
C16	0.0179 (3)	0.0134 (3)	0.0165 (3)	−0.0006 (2)	−0.0003 (2)	−0.0025 (2)
C17	0.0190 (3)	0.0126 (3)	0.0170 (3)	−0.0016 (2)	0.0007 (2)	−0.0017 (2)
C18	0.0168 (3)	0.0181 (3)	0.0150 (3)	−0.0054 (2)	0.0012 (2)	−0.0026 (2)
C19	0.0135 (3)	0.0210 (3)	0.0135 (3)	−0.0019 (2)	−0.0009 (2)	−0.0027 (2)
C20	0.0142 (3)	0.0159 (3)	0.0177 (3)	−0.0019 (2)	0.0001 (2)	−0.0039 (2)
C21	0.0144 (3)	0.0169 (3)	0.0152 (3)	−0.0003 (2)	−0.0026 (2)	−0.0037 (2)
C22	0.0169 (3)	0.0163 (3)	0.0135 (3)	0.0020 (2)	−0.0008 (2)	−0.0005 (2)
C23	0.0198 (3)	0.0161 (3)	0.0136 (3)	−0.0008 (2)	0.0009 (2)	−0.0015 (2)

Geometric parameters (Å, º) top

O1—C23	1.4221 (9)	C11—C12	1.3879 (13)
O1—H1O1	0.896 (16)	C11—H11A	0.9500
N1—C1	1.4284 (10)	C12—C13	1.3941 (11)
N1—C14	1.4327 (9)	C12—H12A	0.9500
N1—C15	1.4669 (9)	C13—C14	1.4002 (11)
N2—C21	1.4719 (9)	C13—H13A	0.9500
N2—C17	1.4750 (10)	C15—C16	1.5295 (10)
N2—C18	1.4766 (9)	C15—H15A	0.9900
N3—C20	1.4633 (9)	C15—H15B	0.9900
N3—C19	1.4641 (9)	C16—C17	1.5275 (11)
N3—C22	1.4644 (10)	C16—H16A	0.9900
C1—C2	1.3988 (10)	C16—H16B	0.9900
C1—C6	1.4109 (11)	C17—H17A	0.9900
C2—C3	1.3932 (11)	C17—H17B	0.9900
C2—H2A	0.9500	C18—C19	1.5160 (11)
C3—C4	1.3908 (13)	C18—H18A	0.9900
C3—H3A	0.9500	C18—H18B	0.9900
C4—C5	1.3900 (13)	C19—H19A	0.9900
C4—H4A	0.9500	C19—H19B	0.9900
C5—C6	1.4057 (11)	C20—C21	1.5168 (11)
C5—H5A	0.9500	C20—H20A	0.9900
C6—C7	1.4641 (11)	C20—H20B	0.9900
C7—C8	1.3446 (12)	C21—H21A	0.9900
C7—H7A	0.9500	C21—H21B	0.9900
C8—C9	1.4644 (12)	C22—C23	1.5163 (10)
C8—H8A	0.9500	C22—H22A	0.9900
C9—C10	1.4029 (11)	C22—H22B	0.9900
C9—C14	1.4072 (10)	C23—H23A	0.9900
C10—C11	1.3870 (13)	C23—H23B	0.9900
C10—H10A	0.9500

C23—O1—H1O1	105.3 (10)	N1—C15—H15A	109.1
C1—N1—C14	114.65 (6)	C16—C15—H15A	109.1
C1—N1—C15	116.37 (6)	N1—C15—H15B	109.1
C14—N1—C15	116.79 (6)	C16—C15—H15B	109.1
C21—N2—C17	110.88 (6)	H15A—C15—H15B	107.8
C21—N2—C18	107.94 (6)	C17—C16—C15	112.28 (6)
C17—N2—C18	109.61 (6)	C17—C16—H16A	109.1
C20—N3—C19	107.69 (5)	C15—C16—H16A	109.1
C20—N3—C22	111.24 (6)	C17—C16—H16B	109.1
C19—N3—C22	110.21 (6)	C15—C16—H16B	109.1
C2—C1—C6	119.36 (7)	H16A—C16—H16B	107.9
C2—C1—N1	121.07 (7)	N2—C17—C16	113.42 (6)
C6—C1—N1	119.49 (6)	N2—C17—H17A	108.9
C3—C2—C1	121.06 (8)	C16—C17—H17A	108.9
C3—C2—H2A	119.5	N2—C17—H17B	108.9
C1—C2—H2A	119.5	C16—C17—H17B	108.9
C4—C3—C2	119.84 (8)	H17A—C17—H17B	107.7
C4—C3—H3A	120.1	N2—C18—C19	110.53 (6)
C2—C3—H3A	120.1	N2—C18—H18A	109.5
C5—C4—C3	119.69 (8)	C19—C18—H18A	109.5
C5—C4—H4A	120.2	N2—C18—H18B	109.5
C3—C4—H4A	120.2	C19—C18—H18B	109.5
C4—C5—C6	121.32 (8)	H18A—C18—H18B	108.1
C4—C5—H5A	119.3	N3—C19—C18	110.52 (6)
C6—C5—H5A	119.3	N3—C19—H19A	109.5
C5—C6—C1	118.73 (7)	C18—C19—H19A	109.5
C5—C6—C7	118.10 (7)	N3—C19—H19B	109.5
C1—C6—C7	123.14 (7)	C18—C19—H19B	109.5
C8—C7—C6	127.21 (7)	H19A—C19—H19B	108.1
C8—C7—H7A	116.4	N3—C20—C21	111.04 (6)
C6—C7—H7A	116.4	N3—C20—H20A	109.4
C7—C8—C9	125.70 (7)	C21—C20—H20A	109.4
C7—C8—H8A	117.1	N3—C20—H20B	109.4
C9—C8—H8A	117.1	C21—C20—H20B	109.4
C10—C9—C14	118.72 (7)	H20A—C20—H20B	108.0
C10—C9—C8	117.98 (7)	N2—C21—C20	111.61 (6)
C14—C9—C8	123.27 (7)	N2—C21—H21A	109.3
C11—C10—C9	121.56 (8)	C20—C21—H21A	109.3
C11—C10—H10A	119.2	N2—C21—H21B	109.3
C9—C10—H10A	119.2	C20—C21—H21B	109.3
C10—C11—C12	119.42 (7)	H21A—C21—H21B	108.0
C10—C11—H11A	120.3	N3—C22—C23	114.20 (6)
C12—C11—H11A	120.3	N3—C22—H22A	108.7
C11—C12—C13	120.12 (8)	C23—C22—H22A	108.7
C11—C12—H12A	119.9	N3—C22—H22B	108.7
C13—C12—H12A	119.9	C23—C22—H22B	108.7
C12—C13—C14	120.73 (8)	H22A—C22—H22B	107.6
C12—C13—H13A	119.6	O1—C23—C22	109.58 (6)
C14—C13—H13A	119.6	O1—C23—H23A	109.8
C13—C14—C9	119.38 (7)	C22—C23—H23A	109.8
C13—C14—N1	121.65 (7)	O1—C23—H23B	109.8
C9—C14—N1	118.91 (7)	C22—C23—H23B	109.8
N1—C15—C16	112.50 (6)	H23A—C23—H23B	108.2

C14—N1—C1—C2	116.85 (7)	C10—C9—C14—C13	−2.75 (11)
C15—N1—C1—C2	−24.50 (10)	C8—C9—C14—C13	175.33 (7)
C14—N1—C1—C6	−66.45 (9)	C10—C9—C14—N1	174.38 (7)
C15—N1—C1—C6	152.20 (7)	C8—C9—C14—N1	−7.54 (11)
C6—C1—C2—C3	−1.21 (11)	C1—N1—C14—C13	−111.94 (8)
N1—C1—C2—C3	175.49 (7)	C15—N1—C14—C13	29.25 (10)
C1—C2—C3—C4	0.74 (12)	C1—N1—C14—C9	71.01 (8)
C2—C3—C4—C5	0.03 (12)	C15—N1—C14—C9	−147.81 (7)
C3—C4—C5—C6	−0.32 (12)	C1—N1—C15—C16	−158.48 (6)
C4—C5—C6—C1	−0.14 (11)	C14—N1—C15—C16	61.01 (8)
C4—C5—C6—C7	−177.90 (7)	N1—C15—C16—C17	61.73 (8)
C2—C1—C6—C5	0.90 (10)	C21—N2—C17—C16	−67.12 (8)
N1—C1—C6—C5	−175.86 (7)	C18—N2—C17—C16	173.81 (6)
C2—C1—C6—C7	178.53 (7)	C15—C16—C17—N2	175.98 (6)
N1—C1—C6—C7	1.78 (10)	C21—N2—C18—C19	57.76 (8)
C5—C6—C7—C8	−150.54 (8)	C17—N2—C18—C19	178.62 (6)
C1—C6—C7—C8	31.80 (12)	C20—N3—C19—C18	60.33 (8)
C6—C7—C8—C9	3.66 (13)	C22—N3—C19—C18	−178.17 (6)
C7—C8—C9—C10	144.64 (8)	N2—C18—C19—N3	−61.60 (8)
C7—C8—C9—C14	−33.45 (12)	C19—N3—C20—C21	−58.73 (8)
C14—C9—C10—C11	2.62 (12)	C22—N3—C20—C21	−179.59 (6)
C8—C9—C10—C11	−175.56 (7)	C17—N2—C21—C20	−176.59 (6)
C9—C10—C11—C12	−0.88 (13)	C18—N2—C21—C20	−56.52 (8)
C10—C11—C12—C13	−0.73 (12)	N3—C20—C21—N2	58.74 (8)
C11—C12—C13—C14	0.55 (12)	C20—N3—C22—C23	−74.86 (8)
C12—C13—C14—C9	1.22 (11)	C19—N3—C22—C23	165.77 (6)
C12—C13—C14—N1	−175.83 (7)	N3—C22—C23—O1	−69.38 (8)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O1—H1O1···N2ⁱ	0.896 (16)	1.999 (16)	2.8822 (9)	168.3 (14)
C5—H5A···O1ⁱⁱ	0.95	2.41	3.3478 (11)	167

Symmetry codes: (i) x, −y+5/2, z+1/2; (ii) x, −y+3/2, z−1/2.

Experimental details

Crystal data
Chemical formula	C₂₃H₂₉N₃O
M_r	363.49
Crystal system, space group	Monoclinic, P2₁/c
Temperature (K)	100
a, b, c (Å)	12.6215 (2), 10.5929 (2), 14.3629 (2)
β (°)	90.966 (1)
V (Å³)	1920.02 (5)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.08
Crystal size (mm)	0.59 × 0.36 × 0.30

Data collection
Diffractometer	Bruker SMART APEXII CCD area-detector diffractometer
Absorption correction	Multi-scan (SADABS; Bruker, 2009)
T_min, T_max	0.955, 0.977
No. of measured, independent and observed [I > 2σ(I)] reflections	30830, 7949, 6682
R_int	0.026
(sin θ/λ)_max (Å⁻¹)	0.792

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.042, 0.117, 1.03
No. of reflections	7949
No. of parameters	248
H-atom treatment	H atoms treated by a mixture of independent and constrained refinement
Δρ_max, Δρ_min (e Å⁻³)	0.56, −0.25

Computer programs: APEX2 (Bruker, 2009), SAINT (Bruker, 2009), SHELXTL (Sheldrick, 2008) and PLATON (Spek, 2009).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O1—H1O1···N2ⁱ	0.896 (16)	1.999 (16)	2.8822 (9)	168.3 (14)
C5—H5A···O1ⁱⁱ	0.95	2.41	3.3478 (11)	167.4

Symmetry codes: (i) x, −y+5/2, z+1/2; (ii) x, −y+3/2, z−1/2.

Footnotes

‡Thomson Reuters ResearcherID: A-3561-2009.

§Thomson Reuters ResearcherID: C-7581-2009.

Acknowledgements

HKF and WSL thank Universiti Sains Malaysia (USM) for a Research University Grant (No. 1001/PFIZIK/811160). WSL also thanks the Malaysian government and USM for the award of a research fellowship. MSS thanks UOM for research facilities.

References

Allen, F. H., Kennard, O., Watson, D. G., Brammer, L., Orpen, A. G. & Taylor, R. (1987). J. Chem. Soc. Perkin Trans. 2, pp. S1–19. CrossRef Web of Science Google Scholar
Bruker (2009). APEX2, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
Cosier, J. & Glazer, A. M. (1986). J. Appl. Cryst. 19, 105–107. CrossRef CAS Web of Science IUCr Journals Google Scholar
Cremer, D. & Pople, J. A. (1975). J. Am. Chem. Soc. 97, 1354–1358. CrossRef CAS Web of Science Google Scholar
Jasinski, J. P., Pek, A. E., Siddaraju, B. P., Yathirajan, H. S. & Narayana, B. (2010). Acta Cryst. E66, o1979–o1980. Web of Science CSD CrossRef IUCr Journals Google Scholar
Moller, H. J., Volz, H. P., Reimann, I. W. & Stoll, K. D. (2001). J. Clin. Psychopharmacol. 21, 59–65. Web of Science CrossRef PubMed CAS Google Scholar
Nagaraj, B., Yathirajan, H. S. & Lynch, D. E. (2005). Acta Cryst. E61, o1757–o1759. Web of Science CSD CrossRef IUCr Journals Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar
Spek, A. L. (2009). Acta Cryst. D65, 148–155. Web of Science CrossRef CAS IUCr Journals Google Scholar