1,10-Bis(2-amino­phen­oxy)deca­ne

Zhang, Q.-L.; Zhu, X.-C.; Zhang, Y.-Q.; Zhu, B.-X.

doi:10.1107/S1600536807043577

1,10-Bis(2-aminophenoxy)decane

Q.-L. Zhang, X.-C. Zhu, Y.-Q. Zhang and B.-X. Zhu

The crystal structure of the title compound, C₂₂H₃₂N₂O₂, contains two independent molecules, each of which is centrosymmetric. Each molecule, with benzene rings linked by a diether strand, is essentially planar except for H atoms. There are two N—H

O and one N—H

N hydrogen bonds. The molecular packing is also controlled by N—H

π and C—H

π interactions.

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Supporting information

	Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536807043577/rk2040sup1.cif Contains datablocks global, I
	Structure factor file (CIF format) https://doi.org/10.1107/S1600536807043577/rk2040Isup2.hkl Contains datablock I

CCDC reference: 663752

checkCIF report

Key indicators

Single-crystal X-ray study
T = 293 K
Mean (C-C) = 0.003 Å
R factor = 0.048
wR factor = 0.134
Data-to-parameter ratio = 15.5

checkCIF/PLATON results

No syntax errors found



Alert level C
PLAT066_ALERT_1_C Predicted and Reported Transmissions Identical .          ?
PLAT420_ALERT_2_C D-H Without Acceptor       N1     -   H1A    ...          ?

Alert level G
PLAT199_ALERT_1_G Check the Reported _cell_measurement_temperature        293 K
PLAT200_ALERT_1_G Check the Reported _diffrn_ambient_temperature .        293 K

   0 ALERT level A = In general: serious problem
   0 ALERT level B = Potentially serious problem
   2 ALERT level C = Check and explain
   2 ALERT level G = General alerts; check

   3 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
   1 ALERT type 2 Indicator that the structure model may be wrong or deficient
   0 ALERT type 3 Indicator that the structure quality may be low
   0 ALERT type 4 Improvement, methodology, query or suggestion
   0 ALERT type 5 Informative message, check

Comment top

Diamine compounds not only are the materials of preparing dyes, paints, oil dope, but also are the important intermediate of synthesizing Schiff base compounds. Recently, Schiff base metal complexes have been widely investigated for their properties and applications in different fields, such as catalysis (Sabater et al., 2001) and materials chemistry (Lacroix, 2001).

The structure of the title compound C₂₂H₃₂N₂O₂ (I) contains two independent molecules, which occupy the center of symmetry positions in the middle of C11—C11a and C22—C22b bonds, respectively (symmetry codes: (a) -x + 1,-y + 2,-z + 1 and (b) -x + 2,-y,-z). In the molecular structure of the (I), the two phenyl rings were linked by ethereal chain forming a non–coplanar structure (Fig. 1). The crystal structure displays two N—H···O and one N—H···N hydrogen bonds (see hydroge–bond table). In the crystal structure, N—H···π and C—H···π interactions occur between adjacent molecules, with N1—H1A···Cg(2)ⁱ angle of 174.99°, H1A···Cg(2)ⁱ distance of 2.5782 Å, N1···Cg(2)ⁱ distances of 3.436 (2) Å, C7—H7A···Cg(1)ⁱⁱ angle of 137.90°, H7A···Cg(1)ⁱⁱ distance of 3.0698 Å, N1···Cg(1)ⁱⁱ distances of 3.8452 (2) Å, C14—H14A···Cg(1)ⁱⁱⁱ angle of 133.77°, H14A···Cg(1)ⁱⁱⁱ distance of 3.2656 Å, C14···Cg(1)ⁱⁱⁱ distances of 3.966 (2) Å and C21—H21B···Cg(2)^iv angle of 136.73°, H21B···Cg(2))^iv distance of 3.2896 Å, C21···Cg(2)^iv distances of 4.051 (2) Å, respectively. Cg(1)ⁱ, Cg(1)ⁱⁱ, Cg(1)ⁱⁱⁱ and Cg(2)^iv are the centroid of the C1–C6 benzene and C12—C17 benzene rings (symmetry codes: (i) -x + y, y, z; (ii) 1 + x, y, z; (iii) x, 1 + y, z; (iv) 1 + x, -1 + y, z).

Related literature top

For related literature, see: Lacroix (2001); Sabater et al. (2001).

Cg1 and Cg2 are the centroids of the C1–C6 and C12–C17 benzene rings

Experimental top

p–Toluenesulfonyl chloride (7.62 g, 40 mmol) was added slowly, whilst stirring, to a pyridine solution (50 ml) containing 1,10–hexanediol (3.48 g, 20 mmol). The mixture was stirred for about 4 h in the range of 268–278 K. Water (40 ml) was added to the resulting solution, the precipitate was collected by filtration, the solid product was crystallized using ethanol. The solid product (0.852 g, 2 mmol) dissolved in DMF (100 ml) containing K₂CO₃ (2 g), o–hydroxyaniline (0.38 g, 4 mmol) was added slowly, to the DMF solution and the mixture was heated at 353 K for 10 h and then the solvent was removed under reduced pressure. The crude product was purified by column chromatography over silica gel using 80% dichloromethane–hexane to afford pure crystals (I), 0.492 g, a yield of 81%. Single crystals suitable for X–ray diffraction were obtained from the 60% C₂H₅OH–CH₂Cl₂ mixture by slow evaporation at room temperature.

Structure description top

For related literature, see: Lacroix (2001); Sabater et al. (2001).

Cg1 and Cg2 are the centroids of the C1–C6 and C12–C17 benzene rings

Computing details top

Data collection: APEX2 (Bruker, 2005); cell refinement: SAINT (Bruker, 2002); data reduction: SAINT (Bruker, 2002); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997); software used to prepare material for publication: WinGX (Farrugia, 1999).

Figures top

Fig. 1. The molecular structure of (I) with the numbering scheme. Displacement ellipsoids are shown with 30% probability level (symmetry codes:(a) -x + 1, -y + 2, -z + 1; (b) -x + 2, -y, -z).

1,10-Bis(2-aminophenoxy)decane top

Crystal data top

C₂₂H₃₂N₂O₂	Z = 2
M_r = 356.50	F(000) = 388
Triclinic, P1	D_x = 1.125 Mg m⁻³
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 6.0138 (9) Å	Cell parameters from 11351 reflections
b = 7.1653 (10) Å	θ = 0.8–25.0°
c = 25.932 (4) Å	µ = 0.07 mm⁻¹
α = 84.666 (6)°	T = 293 K
β = 88.774 (7)°	Prism, colourless
γ = 71.078 (4)°	0.18 × 0.13 × 0.08 mm
V = 1052.4 (3) Å³

Data collection top

Bruker APEX II CCD area-detector diffractometer	3651 independent reflections
Radiation source: Fine–focus sealed tube	2303 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.030
φ– and ω–scan	θ_max = 25.0°, θ_min = 0.8°
Absorption correction: multi-scan (SADABS; Bruker, 2002)	h = −7→6
T_min = 0.987, T_max = 0.993	k = −8→8
11351 measured reflections	l = −30→29

Refinement top

Refinement on F²	Secondary atom site location: Difmap
Least-squares matrix: Full	Hydrogen site location: Geom
R[F² > 2σ(F²)] = 0.048	H-atom parameters constrained
wR(F²) = 0.134	w = 1/[σ²(F_o²) + (0.0602P)² + 0.0396P] where P = (F_o² + 2F_c²)/3
S = 1.06	(Δ/σ)_max < 0.001
3651 reflections	Δρ_max = 0.15 e Å⁻³
235 parameters	Δρ_min = −0.11 e Å⁻³
0 restraints	Extinction correction: SHELXL97, Fc^*=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4
Primary atom site location: Direct	Extinction coefficient: 0.128

Crystal data top

C₂₂H₃₂N₂O₂	γ = 71.078 (4)°
M_r = 356.50	V = 1052.4 (3) Å³
Triclinic, P1	Z = 2
a = 6.0138 (9) Å	Mo Kα radiation
b = 7.1653 (10) Å	µ = 0.07 mm⁻¹
c = 25.932 (4) Å	T = 293 K
α = 84.666 (6)°	0.18 × 0.13 × 0.08 mm
β = 88.774 (7)°

Data collection top

Bruker APEX II CCD area-detector diffractometer	3651 independent reflections
Absorption correction: multi-scan (SADABS; Bruker, 2002)	2303 reflections with I > 2σ(I)
T_min = 0.987, T_max = 0.993	R_int = 0.030
11351 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.048	0 restraints
wR(F²) = 0.134	H-atom parameters constrained
S = 1.06	Δρ_max = 0.15 e Å⁻³
3651 reflections	Δρ_min = −0.11 e Å⁻³
235 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 > 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
C1	−0.4800 (3)	0.6252 (2)	0.30398 (7)	0.0635 (5)
C2	−0.6094 (3)	0.5138 (3)	0.28764 (7)	0.0712 (5)
H2	−0.7256	0.5696	0.2624	0.085*
C3	−0.5696 (4)	0.3215 (3)	0.30801 (8)	0.0756 (6)
H3	−0.6589	0.2485	0.2967	0.091*
C4	−0.3988 (4)	0.2378 (3)	0.34489 (8)	0.0781 (6)
H4	−0.3713	0.1075	0.3586	0.094*
C5	−0.2663 (3)	0.3465 (3)	0.36198 (7)	0.0719 (5)
H5	−0.1489	0.2888	0.3868	0.086*
C6	−0.3083 (3)	0.5398 (2)	0.34220 (7)	0.0605 (5)
C7	−0.0239 (3)	0.5993 (3)	0.39754 (7)	0.0689 (5)
H7A	0.1087	0.4899	0.3875	0.083*
H7B	−0.0911	0.5554	0.4288	0.083*
C8	0.0530 (3)	0.7731 (3)	0.40642 (7)	0.0718 (5)
H8A	−0.0840	0.8810	0.4153	0.086*
H8B	0.1138	0.8163	0.3742	0.086*
C9	0.2379 (3)	0.7359 (3)	0.44833 (7)	0.0715 (5)
H9A	0.3784	0.6316	0.4393	0.086*
H9B	0.1800	0.6916	0.4808	0.086*
C10	0.2990 (4)	0.9216 (3)	0.45502 (8)	0.0779 (6)
H10A	0.3592	0.9624	0.4224	0.093*
H10B	0.1553	1.0262	0.4622	0.093*
C11	0.4746 (4)	0.9042 (3)	0.49681 (7)	0.0765 (6)
H11A	0.6206	0.8031	0.4892	0.092*
H11B	0.4171	0.8605	0.5294	0.092*
C12	−0.0083 (3)	0.9033 (3)	0.18955 (8)	0.0685 (5)
C13	−0.1008 (4)	1.0721 (3)	0.21528 (8)	0.0787 (6)
H13	−0.2335	1.0855	0.2356	0.094*
C14	−0.0016 (4)	1.2196 (3)	0.21158 (8)	0.0837 (6)
H14	−0.0656	1.3304	0.2298	0.100*
C15	0.1925 (4)	1.2053 (3)	0.18105 (8)	0.0830 (6)
H15	0.2596	1.3059	0.1784	0.100*
C16	0.2869 (4)	1.0378 (3)	0.15426 (7)	0.0780 (6)
H16	0.4174	1.0267	0.1334	0.094*
C17	0.1884 (3)	0.8893 (3)	0.15847 (7)	0.0669 (5)
C18	0.4753 (3)	0.6741 (3)	0.10493 (8)	0.0823 (6)
H18A	0.6034	0.6890	0.1245	0.099*
H18B	0.4489	0.7643	0.0737	0.099*
C19	0.5331 (4)	0.4638 (3)	0.09153 (8)	0.0840 (6)
H19A	0.3967	0.4508	0.0748	0.101*
H19B	0.5623	0.3771	0.1234	0.101*
C20	0.7430 (4)	0.3932 (3)	0.05650 (8)	0.0837 (6)
H20A	0.7179	0.4812	0.0249	0.100*
H20B	0.8823	0.3987	0.0736	0.100*
C21	0.7829 (4)	0.1840 (3)	0.04315 (8)	0.0831 (6)
H21A	0.6402	0.1792	0.0274	0.100*
H21B	0.8104	0.0973	0.0750	0.100*
C22	0.9851 (4)	0.1039 (3)	0.00703 (8)	0.0842 (6)
H22A	1.1292	0.1034	0.0232	0.101*
H22B	0.9607	0.1923	−0.0245	0.101*
N1	−0.5123 (3)	0.8182 (2)	0.28294 (7)	0.0932 (6)
H1A	−0.6158	0.8717	0.2589	0.112*
H1B	−0.4288	0.8838	0.2940	0.112*
N2	−0.1044 (3)	0.7523 (2)	0.19298 (8)	0.0967 (6)
H2A	−0.2266	0.7609	0.2117	0.116*
H2B	−0.0422	0.6495	0.1764	0.116*
O1	−0.1958 (2)	0.66528 (17)	0.35693 (5)	0.0776 (4)
O2	0.2675 (2)	0.71497 (19)	0.13528 (5)	0.0870 (4)

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
C1	0.0744 (13)	0.0562 (10)	0.0565 (12)	−0.0163 (9)	−0.0026 (10)	−0.0052 (9)
C2	0.0774 (13)	0.0620 (11)	0.0697 (13)	−0.0150 (10)	−0.0127 (10)	−0.0081 (10)
C3	0.0862 (15)	0.0600 (12)	0.0819 (15)	−0.0226 (10)	−0.0104 (12)	−0.0150 (10)
C4	0.0996 (16)	0.0516 (10)	0.0811 (15)	−0.0210 (11)	−0.0091 (13)	−0.0060 (10)
C5	0.0818 (14)	0.0577 (11)	0.0692 (13)	−0.0127 (10)	−0.0145 (10)	−0.0041 (9)
C6	0.0706 (12)	0.0545 (10)	0.0572 (11)	−0.0199 (9)	−0.0007 (10)	−0.0100 (9)
C7	0.0722 (12)	0.0665 (11)	0.0657 (12)	−0.0174 (9)	−0.0082 (10)	−0.0100 (9)
C8	0.0751 (13)	0.0745 (12)	0.0678 (13)	−0.0258 (10)	−0.0019 (10)	−0.0094 (10)
C9	0.0701 (13)	0.0744 (12)	0.0718 (13)	−0.0232 (10)	−0.0004 (11)	−0.0155 (10)
C10	0.0813 (14)	0.0875 (14)	0.0717 (14)	−0.0357 (11)	−0.0031 (11)	−0.0098 (11)
C11	0.0800 (14)	0.0836 (13)	0.0713 (13)	−0.0314 (11)	0.0019 (11)	−0.0171 (11)
C12	0.0578 (12)	0.0695 (12)	0.0718 (13)	−0.0081 (9)	−0.0058 (10)	−0.0184 (10)
C13	0.0692 (13)	0.0708 (12)	0.0873 (15)	−0.0066 (10)	0.0103 (11)	−0.0233 (11)
C14	0.0916 (16)	0.0645 (12)	0.0877 (16)	−0.0112 (11)	0.0103 (13)	−0.0233 (11)
C15	0.0924 (16)	0.0689 (12)	0.0864 (15)	−0.0219 (11)	0.0094 (13)	−0.0178 (11)
C16	0.0753 (14)	0.0830 (13)	0.0686 (13)	−0.0146 (11)	0.0096 (11)	−0.0135 (11)
C17	0.0633 (12)	0.0667 (11)	0.0614 (12)	−0.0046 (9)	−0.0066 (10)	−0.0180 (9)
C18	0.0674 (13)	0.0959 (15)	0.0747 (14)	−0.0076 (11)	0.0027 (11)	−0.0329 (11)
C19	0.0795 (14)	0.0854 (14)	0.0709 (14)	−0.0004 (11)	0.0080 (11)	−0.0235 (11)
C20	0.0734 (14)	0.0885 (14)	0.0745 (14)	−0.0009 (11)	0.0033 (11)	−0.0260 (11)
C21	0.0785 (14)	0.0827 (13)	0.0691 (14)	0.0022 (11)	0.0077 (11)	−0.0168 (11)
C22	0.0753 (14)	0.0820 (13)	0.0768 (14)	0.0031 (11)	0.0079 (12)	−0.0207 (11)
N1	0.1217 (15)	0.0657 (10)	0.0945 (13)	−0.0383 (10)	−0.0410 (11)	0.0212 (9)
N2	0.0746 (12)	0.0878 (12)	0.1345 (16)	−0.0260 (10)	0.0147 (11)	−0.0475 (11)
O1	0.0927 (10)	0.0660 (8)	0.0765 (9)	−0.0300 (7)	−0.0240 (8)	0.0033 (7)
O2	0.0780 (9)	0.0863 (9)	0.0933 (10)	−0.0135 (7)	0.0158 (8)	−0.0417 (8)

Geometric parameters (Å, º) top

C1—C2	1.379 (2)	C12—C17	1.398 (3)
C1—N1	1.392 (2)	C13—C14	1.368 (3)
C1—C6	1.394 (2)	C13—H13	0.9300
C2—C3	1.375 (2)	C14—C15	1.378 (3)
C2—H2	0.9300	C14—H14	0.9300
C3—C4	1.366 (3)	C15—C16	1.393 (3)
C3—H3	0.9300	C15—H15	0.9300
C4—C5	1.386 (2)	C16—C17	1.371 (3)
C4—H4	0.9300	C16—H16	0.9300
C5—C6	1.375 (2)	C17—O2	1.375 (2)
C5—H5	0.9300	C18—O2	1.425 (2)
C6—O1	1.3713 (19)	C18—C19	1.505 (3)
C7—O1	1.428 (2)	C18—H18A	0.9700
C7—C8	1.500 (2)	C18—H18B	0.9700
C7—H7A	0.9700	C19—C20	1.515 (3)
C7—H7B	0.9700	C19—H19A	0.9700
C8—C9	1.515 (2)	C19—H19B	0.9700
C8—H8A	0.9700	C20—C21	1.511 (3)
C8—H8B	0.9700	C20—H20A	0.9700
C9—C10	1.516 (2)	C20—H20B	0.9700
C9—H9A	0.9700	C21—C22	1.511 (3)
C9—H9B	0.9700	C21—H21A	0.9700
C10—C11	1.498 (2)	C21—H21B	0.9700
C10—H10A	0.9700	C22—C22ⁱⁱ	1.518 (4)
C10—H10B	0.9700	C22—H22A	0.9700
C11—C11ⁱ	1.523 (3)	C22—H22B	0.9700
C11—H11A	0.9700	N1—H1A	0.8600
C11—H11B	0.9700	N1—H1B	0.8600
C12—N2	1.378 (2)	N2—H2A	0.8600
C12—C13	1.384 (2)	N2—H2B	0.8600

C2—C1—N1	122.20 (18)	C14—C13—H13	119.2
C2—C1—C6	118.71 (16)	C12—C13—H13	119.2
N1—C1—C6	119.08 (16)	C13—C14—C15	120.43 (18)
C3—C2—C1	121.09 (18)	C13—C14—H14	119.8
C3—C2—H2	119.5	C15—C14—H14	119.8
C1—C2—H2	119.5	C14—C15—C16	118.99 (19)
C4—C3—C2	119.90 (18)	C14—C15—H15	120.5
C4—C3—H3	120.0	C16—C15—H15	120.5
C2—C3—H3	120.0	C17—C16—C15	120.4 (2)
C3—C4—C5	120.13 (18)	C17—C16—H16	119.8
C3—C4—H4	119.9	C15—C16—H16	119.8
C5—C4—H4	119.9	C16—C17—O2	126.19 (19)
C6—C5—C4	120.02 (18)	C16—C17—C12	120.68 (17)
C6—C5—H5	120.0	O2—C17—C12	113.11 (17)
C4—C5—H5	120.0	O2—C18—C19	106.50 (17)
O1—C6—C5	125.87 (17)	O2—C18—H18A	110.4
O1—C6—C1	114.00 (15)	C19—C18—H18A	110.4
C5—C6—C1	120.12 (16)	O2—C18—H18B	110.4
O1—C7—C8	106.42 (14)	C19—C18—H18B	110.4
O1—C7—H7A	110.4	H18A—C18—H18B	108.6
C8—C7—H7A	110.4	C18—C19—C20	115.17 (18)
O1—C7—H7B	110.4	C18—C19—H19A	108.5
C8—C7—H7B	110.4	C20—C19—H19A	108.5
H7A—C7—H7B	108.6	C18—C19—H19B	108.5
C7—C8—C9	115.48 (16)	C20—C19—H19B	108.5
C7—C8—H8A	108.4	H19A—C19—H19B	107.5
C9—C8—H8A	108.4	C21—C20—C19	111.83 (18)
C7—C8—H8B	108.4	C21—C20—H20A	109.3
C9—C8—H8B	108.4	C19—C20—H20A	109.3
H8A—C8—H8B	107.5	C21—C20—H20B	109.3
C8—C9—C10	111.26 (16)	C19—C20—H20B	109.3
C8—C9—H9A	109.4	H20A—C20—H20B	107.9
C10—C9—H9A	109.4	C20—C21—C22	115.31 (18)
C8—C9—H9B	109.4	C20—C21—H21A	108.4
C10—C9—H9B	109.4	C22—C21—H21A	108.4
H9A—C9—H9B	108.0	C20—C21—H21B	108.4
C11—C10—C9	115.99 (17)	C22—C21—H21B	108.4
C11—C10—H10A	108.3	H21A—C21—H21B	107.5
C9—C10—H10A	108.3	C21—C22—C22ⁱⁱ	113.9 (2)
C11—C10—H10B	108.3	C21—C22—H22A	108.8
C9—C10—H10B	108.3	C22ⁱⁱ—C22—H22A	108.8
H10A—C10—H10B	107.4	C21—C22—H22B	108.8
C10—C11—C11ⁱ	114.2 (2)	C22ⁱⁱ—C22—H22B	108.8
C10—C11—H11A	108.7	H22A—C22—H22B	107.7
C11ⁱ—C11—H11A	108.7	C1—N1—H1A	120.0
C10—C11—H11B	108.7	C1—N1—H1B	120.0
C11ⁱ—C11—H11B	108.7	H1A—N1—H1B	120.0
H11A—C11—H11B	107.6	C12—N2—H2A	120.0
N2—C12—C13	122.54 (19)	C12—N2—H2B	120.0
N2—C12—C17	119.55 (17)	H2A—N2—H2B	120.0
C13—C12—C17	117.90 (19)	C6—O1—C7	119.66 (13)
C14—C13—C12	121.6 (2)	C17—O2—C18	119.54 (16)

N1—C1—C2—C3	178.13 (19)	C13—C14—C15—C16	−0.4 (3)
C6—C1—C2—C3	−0.7 (3)	C14—C15—C16—C17	−0.3 (3)
C1—C2—C3—C4	−0.3 (3)	C15—C16—C17—O2	−178.22 (17)
C2—C3—C4—C5	0.3 (3)	C15—C16—C17—C12	0.1 (3)
C3—C4—C5—C6	0.7 (3)	N2—C12—C17—C16	179.78 (18)
C4—C5—C6—O1	177.70 (17)	C13—C12—C17—C16	0.7 (3)
C4—C5—C6—C1	−1.7 (3)	N2—C12—C17—O2	−1.7 (3)
C2—C1—C6—O1	−177.78 (16)	C13—C12—C17—O2	179.23 (16)
N1—C1—C6—O1	3.4 (2)	O2—C18—C19—C20	176.78 (17)
C2—C1—C6—C5	1.7 (3)	C18—C19—C20—C21	−177.64 (17)
N1—C1—C6—C5	−177.21 (18)	C19—C20—C21—C22	178.32 (17)
O1—C7—C8—C9	−179.84 (15)	C20—C21—C22—C22ⁱⁱ	−178.0 (2)
C7—C8—C9—C10	−178.70 (16)	C5—C6—O1—C7	−2.4 (3)
C8—C9—C10—C11	177.98 (16)	C1—C6—O1—C7	177.03 (15)
C9—C10—C11—C11ⁱ	−178.3 (2)	C8—C7—O1—C6	−176.43 (15)
N2—C12—C13—C14	179.58 (19)	C16—C17—O2—C18	2.3 (3)
C17—C12—C13—C14	−1.3 (3)	C12—C17—O2—C18	−176.21 (17)
C12—C13—C14—C15	1.2 (3)	C19—C18—O2—C17	172.20 (15)

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

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N2—H2A···N1	0.86	2.47	3.300 (3)	163
N1—H1B···O1	0.86	2.30	2.630 (2)	103
N2—H2B···O2	0.86	2.28	2.618 (2)	103

Experimental details

Crystal data
Chemical formula	C₂₂H₃₂N₂O₂
M_r	356.50
Crystal system, space group	Triclinic, P1
Temperature (K)	293
a, b, c (Å)	6.0138 (9), 7.1653 (10), 25.932 (4)
α, β, γ (°)	84.666 (6), 88.774 (7), 71.078 (4)
V (Å³)	1052.4 (3)
Z	2
Radiation type	Mo Kα
µ (mm⁻¹)	0.07
Crystal size (mm)	0.18 × 0.13 × 0.08

Data collection
Diffractometer	Bruker APEX II CCD area-detector
Absorption correction	Multi-scan (SADABS; Bruker, 2002)
T_min, T_max	0.987, 0.993
No. of measured, independent and observed [I > 2σ(I)] reflections	11351, 3651, 2303
R_int	0.030
(sin θ/λ)_max (Å⁻¹)	0.595

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.048, 0.134, 1.06
No. of reflections	3651
No. of parameters	235
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.15, −0.11

Computer programs: APEX2 (Bruker, 2005), SAINT (Bruker, 2002), SHELXS97 (Sheldrick, 1997), SHELXL97 (Sheldrick, 1997), ORTEP-3 for Windows (Farrugia, 1997), WinGX (Farrugia, 1999).