2,2′-[(Propane-1,3-diyldinitrilo)bis­(phenyl­methyl­idyne)]diphenol

Black, R.S.; Billing, D.G.; Bartyzel, A.; Cukrowska, E.

doi:10.1107/S1600536810011189

organic compounds

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ISSN: 2056-9890

Volume 66| Part 4| April 2010| Pages o1002-o1003

doi:10.1107/S1600536810011189

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2,2′-[(Propane-1,3-diyldinitrilo)bis(phenylmethylidyne)]diphenol

Robert S. Black,^a David G. Billing,^a ^* Agata Bartyzel ^a ‡ and Ewa Cukrowska ^a

^aMolecular Sciences Institute, School of Chemistry, University of the Witwatersrand, Private Bag 3, PO Wits 2050, South Africa
^*Correspondence e-mail: dave.billing@wits.ac.za

(Received 9 March 2010; accepted 24 March 2010; online 31 March 2010)

In the title molecule, C₂₉H₂₆N₂O₂, there are two strong intramolecular O—H⋯N hydrogen bonds involving the hydroxy and imine groups, forming S(6) ring motifs. The dihedral angles between adjacent phenyl rings and phenol-containing planes are 85.27 (19) and 91.38 (18)°. In the crystal structure, weak intermolecular C—H⋯O hydrogen bonds connect molecules into a two-dimensional network.

Related literature

The title compound forms part of the group of Schiff bases with a similar method of synthesis as described in Schilf et al. (2007 ). The intermolecular hydrogen bonds O—H⋯N between the hydroxy and imine are common to this type of compound as shown with the series of compounds reported by Fernández et al. (2001 ); Kabak (2003 ); Wojciechowski et al. (2001 ); Dey et al. (2001 ); Koşar, et al. (2004 ); Lu, et al. (2008 ); Qiu & Zhao (2008 ); Montazerozohori et al. (2009 ); Corden et al. (1996 ). For a decription of hydrogen-bond motifs, see: Bernstein et al. (1995 ).

Experimental

Crystal data

C₂₉H₂₆N₂O₂
M_r = 434.52
Monoclinic, P 2₁ /c
a = 18.226 (2) Å
b = 8.2303 (9) Å
c = 18.642 (2) Å
β = 119.086 (5)°
V = 2443.7 (5) Å³
Z = 4
Mo Kα radiation
μ = 0.07 mm⁻¹
T = 293 K
0.7 × 0.5 × 0.28 mm

Data collection

Bruker SMART 1K CCD area-detector diffractometer
21350 measured reflections
5896 independent reflections
3749 reflections with I > 2σ(I)
R_int = 0.071

Refinement

R[F² > 2σ(F²)] = 0.055
wR(F²) = 0.173
S = 1.03
5896 reflections
300 parameters
H-atom parameters constrained
Δρ_max = 0.23 e Å⁻³
Δρ_min = −0.36 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O1—H1A⋯N1	0.82	1.80	2.5344 (17)	148
O2—H2A⋯N2	0.82	1.81	2.5431 (18)	148
C17—H17⋯O2ⁱ	0.93	2.56	3.481 (2)	168
C18—H18⋯O1ⁱⁱ	0.93	2.47	3.395 (3)	174
C21—H21⋯O2ⁱⁱⁱ	0.93	2.56	3.492 (2)	175
Symmetry codes: (i) $[-x+1, y+{\script{1\over 2}}, -z+{\script{1\over 2}}]$ ; (ii) -x+1, -y+1, -z+1; (iii) $[-x+1, y-{\script{1\over 2}}, -z+{\script{1\over 2}}]$ .

Data collection: SMART-NT (Bruker, 1998 ); cell refinement: SAINT-Plus (Bruker, 1999 ); data reduction: SAINT-Plus; 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: WinGX (Farrugia, 1999 ) and PLATON.

Supporting information

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536810011189/lh5012sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536810011189/lh5012Isup2.hkl

checkCIF report

Comment top

The molecular structure of the title compound is shown in Fig. 1. There are two strong intramolecular O—H..O hydrogen bonds involving the hydroxyl and imine groups forming S(6) ring motifs (Bernstein et al., 1995). These types of hydrogen bonds are common to some reported molecular structures (Schilf et al., 2007; Fernández et al., 2001; Kabak, 2003; Wojciechowski et al., 2001; Dey et al., 2001; Koşar, et al., 2004; Lu, et al., 2008; Qiu & Zhao, 2008; Montazerozohori et al., 2009; Corden et al., 1996). In the crystal structure, weak intermolecular C—H···O hydrogen bond connect molecules to form a two-dimensional network.

Related literature top

The title compound forms part of the group of Schiff bases with a similar method of synthesis as described in Schilf et al. (2007). The intermolecular hydrogen bonds O—H···N between the hydroxy and imine are common to this type of compound as shown with the series of compounds reported by Fernández et al. (2001); Kabak (2003); Wojciechowski et al. (2001); Dey et al. (2001); Koşar, et al. (2004); Lu, et al. (2008); Qiu & Zhao (2008); Montazerozohori et al. (2009); Corden et al. (1996). For a decription of hydrogen-bond motifs, see: Bernstein et al. (1995).

Experimental top

A mixture of 1.0 mmol (2.00 g) of 2-hydroxybenzophenone, 0.5 mmole (0.42 cm³) of 1,3-propanediamine and 2 drops of glacial acetic acid in 40 ml of methanol was refluxed for 8 h. The excess of solvent (ca. 30 ml) was then evaporated. After cooling to 277 K a yellow solid was produced. The polycrystalline product was collected by filtration, washed with methanol and dried. A yield of 52% was obtained. Recrystalization from an ethanol solution yielded single crystals suitable for x-ray diffraction. Elemental analysis C% 79.67 H% 6.26 N% 6.11%.

Computing details top

Data collection: SMART-NT (Bruker, 1998); cell refinement: SAINT-Plus (Bruker, 1999); data reduction: SAINT-Plus (Bruker, 1999); program(s) used to solve structure: SHELXSL97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: PLATON (Spek, 2009); software used to prepare material for publication: WinGX (Farrugia, 1999) and PLATON (Spek, 2009).

Figures top

Fig. 1. The molecular structure of the title compound with displacement ellipsoids drawn at the 30% probability level. Hydrogen bonds are shown as dashed lines.

2,2'-[(Propane-1,3-diyldinitrilo)bis(phenylmethylidyne)]diphenol top

Crystal data top

C₂₉H₂₆N₂O₂	F(000) = 920
M_r = 434.52	D_x = 1.181 Mg m⁻³
Monoclinic, P2₁/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 21350 reflections
a = 18.226 (2) Å	θ = 2.1–23.0°
b = 8.2303 (9) Å	µ = 0.07 mm⁻¹
c = 18.642 (2) Å	T = 293 K
β = 119.086 (5)°	Block, yellow
V = 2443.7 (5) Å³	0.7 × 0.5 × 0.28 mm
Z = 4

Data collection top

Bruker SMART 1K CCD area-detector diffractometer	R_int = 0.071
ϕ and ω scans	θ_max = 28°, θ_min = 1.3°
21350 measured reflections	h = −19→24
5896 independent reflections	k = −10→10
3749 reflections with I > 2σ(I)	l = −24→20

Refinement top

Refinement on F²	0 restraints
Least-squares matrix: full	H-atom parameters constrained
R[F² > 2σ(F²)] = 0.055	w = 1/[σ²(F_o²) + (0.0897P)² + 0.2258P] where P = (F_o² + 2F_c²)/3
wR(F²) = 0.173	(Δ/σ)_max = 0.002
S = 1.03	Δρ_max = 0.23 e Å⁻³
5896 reflections	Δρ_min = −0.36 e Å⁻³
300 parameters

Crystal data top

C₂₉H₂₆N₂O₂	V = 2443.7 (5) Å³
M_r = 434.52	Z = 4
Monoclinic, P2₁/c	Mo Kα radiation
a = 18.226 (2) Å	µ = 0.07 mm⁻¹
b = 8.2303 (9) Å	T = 293 K
c = 18.642 (2) Å	0.7 × 0.5 × 0.28 mm
β = 119.086 (5)°

Data collection top

Bruker SMART 1K CCD area-detector diffractometer	3749 reflections with I > 2σ(I)
21350 measured reflections	R_int = 0.071
5896 independent reflections

Refinement top

R[F² > 2σ(F²)] = 0.055	0 restraints
wR(F²) = 0.173	H-atom parameters constrained
S = 1.03	Δρ_max = 0.23 e Å⁻³
5896 reflections	Δρ_min = −0.36 e Å⁻³
300 parameters

Special details top

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.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å²) top

	x	y	z	U_iso*/U_eq
C1	0.17087 (13)	0.1655 (3)	0.08228 (11)	0.0718 (5)
H1	0.1926	0.2672	0.0813	0.086*
C2	0.15625 (16)	0.0517 (3)	0.02117 (14)	0.0940 (7)
H2	0.1689	0.0776	−0.0201	0.113*
C3	0.12367 (14)	−0.0961 (3)	0.02162 (16)	0.0947 (8)
H3	0.1142	−0.1708	−0.0194	0.114*
C4	0.10480 (16)	−0.1362 (3)	0.08146 (16)	0.0960 (7)
H4	0.0823	−0.2377	0.0812	0.115*
C5	0.11925 (13)	−0.0247 (3)	0.14328 (13)	0.0759 (5)
H5	0.1062	−0.0519	0.1842	0.091*
C6	0.15300 (9)	0.12641 (19)	0.14400 (9)	0.0501 (4)
C7	0.17057 (8)	0.24201 (18)	0.21320 (9)	0.0457 (3)
C8	0.10782 (9)	0.36732 (18)	0.20194 (9)	0.0476 (3)
C9	0.03699 (10)	0.3944 (2)	0.12497 (11)	0.0612 (4)
H9	0.0291	0.3308	0.0805	0.073*
C10	−0.02150 (12)	0.5138 (3)	0.11365 (13)	0.0775 (6)
H10	−0.0675	0.5312	0.062	0.093*
C11	−0.01072 (13)	0.6066 (3)	0.17994 (16)	0.0826 (6)
H11	−0.05	0.6861	0.1726	0.099*
C12	0.05729 (13)	0.5829 (2)	0.25660 (14)	0.0735 (5)
H12	0.0632	0.6461	0.3004	0.088*
C13	0.11810 (10)	0.4642 (2)	0.26941 (10)	0.0548 (4)
C14	0.30624 (10)	0.1168 (2)	0.29798 (11)	0.0637 (4)
H14A	0.3103	0.1037	0.2483	0.076*
H14B	0.2935	0.0117	0.3128	0.076*
C15	0.38907 (10)	0.1788 (2)	0.36662 (10)	0.0590 (4)
H15A	0.385	0.1869	0.4165	0.071*
H15B	0.3992	0.287	0.3528	0.071*
C16	0.46364 (10)	0.0702 (2)	0.38294 (10)	0.0606 (4)
H16A	0.5125	0.1034	0.4336	0.073*
H16B	0.4508	−0.0416	0.3891	0.073*
C17	0.66693 (10)	0.2305 (2)	0.45511 (10)	0.0602 (4)
H17	0.6442	0.3306	0.4316	0.072*
C18	0.73422 (12)	0.2233 (3)	0.53470 (12)	0.0729 (5)
H18	0.756	0.3185	0.5644	0.087*
C19	0.76854 (12)	0.0763 (3)	0.56945 (12)	0.0743 (5)
H19	0.813	0.0721	0.6229	0.089*
C20	0.73734 (12)	−0.0646 (3)	0.52550 (13)	0.0747 (5)
H20	0.7618	−0.1637	0.5489	0.09*
C21	0.66949 (11)	−0.0604 (2)	0.44627 (11)	0.0608 (4)
H21	0.6481	−0.1564	0.4172	0.073*
C22	0.63373 (9)	0.08832 (18)	0.41069 (9)	0.0469 (3)
C23	0.55780 (9)	0.09263 (18)	0.32620 (9)	0.0496 (4)
C24	0.57020 (11)	0.10567 (19)	0.25341 (10)	0.0539 (4)
C25	0.65069 (12)	0.1279 (2)	0.26229 (12)	0.0676 (5)
H25	0.6968	0.134	0.3147	0.081*
C26	0.66269 (15)	0.1409 (3)	0.19441 (15)	0.0808 (6)
H26	0.7163	0.156	0.2012	0.097*
C27	0.59361 (18)	0.1312 (3)	0.11627 (15)	0.0861 (7)
H27	0.6013	0.1387	0.0706	0.103*
C28	0.51399 (16)	0.1106 (2)	0.10547 (12)	0.0769 (6)
H28	0.4686	0.1045	0.0527	0.092*
C29	0.50056 (12)	0.09859 (19)	0.17301 (11)	0.0597 (4)
N1	0.23864 (8)	0.23289 (17)	0.28316 (8)	0.0562 (3)
N2	0.48206 (8)	0.08218 (17)	0.31467 (8)	0.0564 (3)
O1	0.18408 (8)	0.44387 (17)	0.34460 (7)	0.0709 (4)
H1A	0.2167	0.3781	0.3424	0.106*
O2	0.42130 (8)	0.08050 (17)	0.15964 (7)	0.0715 (4)
H2A	0.4218	0.074	0.2038	0.107*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
C1	0.0820 (13)	0.0800 (12)	0.0680 (11)	−0.0146 (10)	0.0478 (10)	−0.0153 (9)
C2	0.1009 (17)	0.125 (2)	0.0795 (14)	−0.0200 (15)	0.0625 (14)	−0.0331 (13)
C3	0.0776 (14)	0.1138 (19)	0.1001 (16)	−0.0262 (13)	0.0490 (13)	−0.0609 (14)
C4	0.0966 (17)	0.0856 (15)	0.1172 (18)	−0.0384 (13)	0.0610 (16)	−0.0465 (14)
C5	0.0807 (13)	0.0769 (12)	0.0816 (13)	−0.0279 (10)	0.0484 (11)	−0.0252 (10)
C6	0.0390 (7)	0.0596 (9)	0.0508 (8)	−0.0030 (6)	0.0212 (6)	−0.0107 (7)
C7	0.0393 (7)	0.0540 (8)	0.0465 (7)	−0.0056 (6)	0.0229 (6)	−0.0073 (6)
C8	0.0400 (7)	0.0531 (8)	0.0529 (8)	−0.0062 (6)	0.0250 (7)	−0.0070 (6)
C9	0.0456 (9)	0.0714 (11)	0.0615 (10)	−0.0002 (7)	0.0220 (8)	−0.0086 (8)
C10	0.0513 (10)	0.0855 (13)	0.0823 (13)	0.0124 (9)	0.0221 (9)	−0.0007 (11)
C11	0.0607 (12)	0.0732 (12)	0.1165 (18)	0.0144 (9)	0.0451 (13)	−0.0065 (12)
C12	0.0679 (12)	0.0709 (12)	0.0926 (14)	0.0000 (9)	0.0475 (11)	−0.0229 (10)
C13	0.0520 (9)	0.0573 (9)	0.0625 (10)	−0.0083 (7)	0.0338 (8)	−0.0127 (7)
C14	0.0450 (9)	0.0724 (11)	0.0627 (10)	0.0065 (7)	0.0175 (8)	−0.0136 (8)
C15	0.0442 (8)	0.0750 (11)	0.0546 (9)	−0.0015 (7)	0.0217 (7)	−0.0083 (8)
C16	0.0435 (8)	0.0848 (12)	0.0528 (9)	0.0052 (8)	0.0229 (7)	0.0092 (8)
C17	0.0553 (9)	0.0568 (9)	0.0662 (10)	−0.0005 (7)	0.0277 (8)	−0.0048 (8)
C18	0.0569 (10)	0.0913 (14)	0.0704 (12)	−0.0188 (10)	0.0310 (9)	−0.0281 (10)
C19	0.0501 (10)	0.1127 (17)	0.0548 (10)	0.0029 (10)	0.0213 (8)	0.0014 (10)
C20	0.0621 (11)	0.0852 (14)	0.0726 (12)	0.0204 (10)	0.0294 (10)	0.0230 (11)
C21	0.0566 (10)	0.0567 (9)	0.0669 (10)	0.0052 (7)	0.0282 (9)	0.0009 (8)
C22	0.0402 (7)	0.0523 (8)	0.0505 (8)	0.0024 (6)	0.0237 (7)	−0.0007 (6)
C23	0.0455 (8)	0.0508 (8)	0.0518 (8)	0.0035 (6)	0.0230 (7)	−0.0005 (6)
C24	0.0605 (9)	0.0511 (8)	0.0554 (9)	0.0042 (7)	0.0324 (8)	−0.0011 (7)
C25	0.0690 (11)	0.0714 (11)	0.0764 (12)	0.0021 (9)	0.0465 (10)	−0.0025 (9)
C26	0.0994 (16)	0.0749 (13)	0.1028 (16)	0.0019 (11)	0.0763 (15)	−0.0001 (11)
C27	0.136 (2)	0.0732 (13)	0.0831 (15)	0.0020 (13)	0.0797 (16)	0.0013 (11)
C28	0.1119 (17)	0.0633 (11)	0.0601 (11)	0.0001 (11)	0.0456 (12)	−0.0017 (8)
C29	0.0754 (12)	0.0501 (9)	0.0562 (9)	0.0028 (8)	0.0340 (9)	−0.0002 (7)
N1	0.0429 (7)	0.0685 (9)	0.0517 (7)	0.0042 (6)	0.0187 (6)	−0.0111 (6)
N2	0.0442 (7)	0.0732 (9)	0.0494 (7)	0.0036 (6)	0.0209 (6)	0.0030 (6)
O1	0.0677 (8)	0.0854 (9)	0.0572 (7)	0.0013 (6)	0.0285 (6)	−0.0219 (6)
O2	0.0667 (8)	0.0858 (9)	0.0505 (6)	−0.0029 (6)	0.0193 (6)	−0.0008 (6)

Geometric parameters (Å, º) top

C1—C6	1.378 (2)	C15—H15B	0.97
C1—C2	1.396 (3)	C16—N2	1.469 (2)
C1—H1	0.93	C16—H16A	0.97
C2—C3	1.356 (3)	C16—H16B	0.97
C2—H2	0.93	C17—C22	1.391 (2)
C3—C4	1.358 (3)	C17—C18	1.393 (3)
C3—H3	0.93	C17—H17	0.93
C4—C5	1.394 (3)	C18—C19	1.371 (3)
C4—H4	0.93	C18—H18	0.93
C5—C6	1.385 (2)	C19—C20	1.374 (3)
C5—H5	0.93	C19—H19	0.93
C6—C7	1.507 (2)	C20—C21	1.392 (3)
C7—N1	1.2934 (19)	C20—H20	0.93
C7—C8	1.477 (2)	C21—C22	1.394 (2)
C8—C9	1.405 (2)	C21—H21	0.93
C8—C13	1.422 (2)	C22—C23	1.509 (2)
C9—C10	1.389 (3)	C23—N2	1.293 (2)
C9—H9	0.93	C23—C24	1.484 (2)
C10—C11	1.383 (3)	C24—C25	1.406 (2)
C10—H10	0.93	C24—C29	1.418 (2)
C11—C12	1.376 (3)	C25—C26	1.389 (3)
C11—H11	0.93	C25—H25	0.93
C12—C13	1.408 (2)	C26—C27	1.389 (3)
C12—H12	0.93	C26—H26	0.93
C13—O1	1.342 (2)	C27—C28	1.375 (3)
C14—N1	1.475 (2)	C27—H27	0.93
C14—C15	1.516 (2)	C28—C29	1.398 (3)
C14—H14A	0.97	C28—H28	0.93
C14—H14B	0.97	C29—O2	1.349 (2)
C15—C16	1.528 (2)	O1—H1A	0.82
C15—H15A	0.97	O2—H2A	0.82

C6—C1—C2	119.74 (19)	H15A—C15—H15B	107.7
C6—C1—H1	120.1	N2—C16—C15	110.13 (13)
C2—C1—H1	120.1	N2—C16—H16A	109.6
C3—C2—C1	120.5 (2)	C15—C16—H16A	109.6
C3—C2—H2	119.8	N2—C16—H16B	109.6
C1—C2—H2	119.8	C15—C16—H16B	109.6
C2—C3—C4	120.63 (19)	H16A—C16—H16B	108.1
C2—C3—H3	119.7	C22—C17—C18	120.06 (16)
C4—C3—H3	119.7	C22—C17—H17	120
C3—C4—C5	119.9 (2)	C18—C17—H17	120
C3—C4—H4	120.1	C19—C18—C17	120.31 (18)
C5—C4—H4	120.1	C19—C18—H18	119.8
C6—C5—C4	120.23 (19)	C17—C18—H18	119.8
C6—C5—H5	119.9	C18—C19—C20	120.11 (17)
C4—C5—H5	119.9	C18—C19—H19	119.9
C1—C6—C5	119.07 (16)	C20—C19—H19	119.9
C1—C6—C7	121.98 (15)	C19—C20—C21	120.55 (17)
C5—C6—C7	118.94 (15)	C19—C20—H20	119.7
N1—C7—C8	118.72 (13)	C21—C20—H20	119.7
N1—C7—C6	121.82 (13)	C20—C21—C22	119.74 (16)
C8—C7—C6	119.45 (12)	C20—C21—H21	120.1
C9—C8—C13	118.36 (14)	C22—C21—H21	120.1
C9—C8—C7	121.28 (13)	C17—C22—C21	119.22 (15)
C13—C8—C7	120.37 (13)	C17—C22—C23	120.95 (13)
C10—C9—C8	121.58 (17)	C21—C22—C23	119.78 (13)
C10—C9—H9	119.2	N2—C23—C24	118.54 (14)
C8—C9—H9	119.2	N2—C23—C22	122.36 (14)
C11—C10—C9	119.33 (19)	C24—C23—C22	119.09 (13)
C11—C10—H10	120.3	C25—C24—C29	118.44 (16)
C9—C10—H10	120.3	C25—C24—C23	121.04 (15)
C12—C11—C10	120.99 (17)	C29—C24—C23	120.51 (15)
C12—C11—H11	119.5	C26—C25—C24	121.34 (19)
C10—C11—H11	119.5	C26—C25—H25	119.3
C11—C12—C13	120.75 (17)	C24—C25—H25	119.3
C11—C12—H12	119.6	C27—C26—C25	119.15 (19)
C13—C12—H12	119.6	C27—C26—H26	120.4
O1—C13—C12	119.70 (15)	C25—C26—H26	120.4
O1—C13—C8	121.33 (14)	C28—C27—C26	120.96 (18)
C12—C13—C8	118.98 (16)	C28—C27—H27	119.5
N1—C14—C15	109.80 (14)	C26—C27—H27	119.5
N1—C14—H14A	109.7	C27—C28—C29	120.7 (2)
C15—C14—H14A	109.7	C27—C28—H28	119.6
N1—C14—H14B	109.7	C29—C28—H28	119.6
C15—C14—H14B	109.7	O2—C29—C28	118.80 (17)
H14A—C14—H14B	108.2	O2—C29—C24	121.83 (15)
C14—C15—C16	113.32 (14)	C28—C29—C24	119.37 (18)
C14—C15—H15A	108.9	C7—N1—C14	122.06 (13)
C16—C15—H15A	108.9	C23—N2—C16	122.40 (13)
C14—C15—H15B	108.9	C13—O1—H1A	109.5
C16—C15—H15B	108.9	C29—O2—H2A	109.5

C6—C1—C2—C3	0.8 (4)	C18—C19—C20—C21	−1.6 (3)
C1—C2—C3—C4	−0.1 (4)	C19—C20—C21—C22	1.0 (3)
C2—C3—C4—C5	−0.2 (4)	C18—C17—C22—C21	−1.1 (2)
C3—C4—C5—C6	−0.2 (4)	C18—C17—C22—C23	176.55 (14)
C2—C1—C6—C5	−1.2 (3)	C20—C21—C22—C17	0.3 (2)
C2—C1—C6—C7	177.65 (19)	C20—C21—C22—C23	−177.36 (15)
C4—C5—C6—C1	0.9 (3)	C17—C22—C23—N2	−90.01 (19)
C4—C5—C6—C7	−177.97 (19)	C21—C22—C23—N2	87.61 (19)
C1—C6—C7—N1	−96.1 (2)	C17—C22—C23—C24	91.38 (18)
C5—C6—C7—N1	82.8 (2)	C21—C22—C23—C24	−91.00 (18)
C1—C6—C7—C8	85.27 (19)	N2—C23—C24—C25	175.86 (15)
C5—C6—C7—C8	−95.88 (19)	C22—C23—C24—C25	−5.5 (2)
N1—C7—C8—C9	173.25 (15)	N2—C23—C24—C29	−3.1 (2)
C6—C7—C8—C9	−8.1 (2)	C22—C23—C24—C29	175.57 (13)
N1—C7—C8—C13	−6.6 (2)	C29—C24—C25—C26	−0.7 (3)
C6—C7—C8—C13	172.08 (13)	C23—C24—C25—C26	−179.70 (16)
C13—C8—C9—C10	1.0 (3)	C24—C25—C26—C27	−0.2 (3)
C7—C8—C9—C10	−178.90 (17)	C25—C26—C27—C28	0.7 (3)
C8—C9—C10—C11	−1.2 (3)	C26—C27—C28—C29	−0.1 (3)
C9—C10—C11—C12	0.5 (3)	C27—C28—C29—O2	179.16 (17)
C10—C11—C12—C13	0.4 (3)	C27—C28—C29—C24	−0.9 (3)
C11—C12—C13—O1	179.67 (18)	C25—C24—C29—O2	−178.77 (16)
C11—C12—C13—C8	−0.6 (3)	C23—C24—C29—O2	0.2 (2)
C9—C8—C13—O1	179.63 (15)	C25—C24—C29—C28	1.2 (2)
C7—C8—C13—O1	−0.5 (2)	C23—C24—C29—C28	−179.77 (15)
C9—C8—C13—C12	−0.1 (2)	C8—C7—N1—C14	−176.84 (14)
C7—C8—C13—C12	179.80 (15)	C6—C7—N1—C14	4.5 (2)
N1—C14—C15—C16	−176.82 (14)	C15—C14—N1—C7	155.47 (15)
C14—C15—C16—N2	70.2 (2)	C24—C23—N2—C16	−179.47 (14)
C22—C17—C18—C19	0.5 (3)	C22—C23—N2—C16	1.9 (2)
C17—C18—C19—C20	0.8 (3)	C15—C16—N2—C23	137.49 (16)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O1—H1A···N1	0.82	1.80	2.5344 (17)	148
O2—H2A···N2	0.82	1.81	2.5431 (18)	148
C17—H17···O2ⁱ	0.93	2.56	3.481 (2)	168
C18—H18···O1ⁱⁱ	0.93	2.47	3.395 (3)	174
C21—H21···O2ⁱⁱⁱ	0.93	2.56	3.492 (2)	175

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

Experimental details

Crystal data
Chemical formula	C₂₉H₂₆N₂O₂
M_r	434.52
Crystal system, space group	Monoclinic, P2₁/c
Temperature (K)	293
a, b, c (Å)	18.226 (2), 8.2303 (9), 18.642 (2)
β (°)	119.086 (5)
V (Å³)	2443.7 (5)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.07
Crystal size (mm)	0.7 × 0.5 × 0.28

Data collection
Diffractometer	Bruker SMART 1K CCD area-detector diffractometer
Absorption correction	–
No. of measured, independent and observed [I > 2σ(I)] reflections	21350, 5896, 3749
R_int	0.071
(sin θ/λ)_max (Å⁻¹)	0.661

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.055, 0.173, 1.03
No. of reflections	5896
No. of parameters	300
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.23, −0.36

Computer programs: SMART-NT (Bruker, 1998), SAINT-Plus (Bruker, 1999), SHELXSL97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), WinGX (Farrugia, 1999) and PLATON (Spek, 2009).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O1—H1A···N1	0.82	1.80	2.5344 (17)	148
O2—H2A···N2	0.82	1.81	2.5431 (18)	148
C17—H17···O2ⁱ	0.93	2.56	3.481 (2)	168
C18—H18···O1ⁱⁱ	0.93	2.47	3.395 (3)	174
C21—H21···O2ⁱⁱⁱ	0.93	2.56	3.492 (2)	175

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

Footnotes

‡On leave from: Faculty of Chemistry Department of General and Coordination Chemistry Maria Curie-Sklodowska University Maria Curie-Sklodowska Sq. 2 20-031 Lublin Poland.

Acknowledgements

The University of the Witwatersrand and the National Research Foundation (GUN 2069064) are thanked for providing the infrastructure and for the award of a research grant required to carry out this work.

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