Opipramol.

IN THE TITLE COMPOUND (SYSTEMATIC NAME: 2-{4-[3-(5H-dibenz[b,f]azepin-5-yl)prop-yl]piperazin-1-yl}ethanol), C(23)H(29)N(3)O, 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 mol-ecules 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 = 363.49

Monoclinic,

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[F 2 > 2σ(F 2)] = 0.042

wR(F 2) = 0.117

S = 1.03

7949 reflections

248 parameters

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.56 e Å−3

Δρmin = −0.25 e Å−3

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 ▶).

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S1600536811021131/is2726sup1.cif

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

Supplementary material file. DOI: 10.1107/S1600536811021131/is2726Isup3.cml

Additional supplementary materials: crystallographic information; 3D view; checkCIF report

C23H29N3O	F(000) = 784
Mr = 363.49	Dx = 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

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

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(Fo2) + (0.0611P)2 + 0.4097P] where P = (Fo2 + 2Fc2)/3
7949 reflections	(Δ/σ)max = 0.001
248 parameters	Δρmax = 0.56 e Å−3
0 restraints	Δρmin = −0.25 e Å−3

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.

	x	y	z	Uiso*/Ueq
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)*

	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)

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)

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.

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) ; (ii) .