1,1′-Bis(3-methyl-3-phenyl­cyclo­but­yl)-2,2′-(aza­nedi­yl)diethanol

Şen, F.; Dinçer, M.; Çukurovalı, A.; Yılmaz, I.

doi:10.1107/S1600536812010203

organic compounds

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ISSN: 2056-9890

Volume 68| Part 4| April 2012| Page o1052

doi:10.1107/S1600536812010203

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1,1′-Bis(3-methyl-3-phenylcyclobutyl)-2,2′-(azanediyl)diethanol

Fatih Şen,^a ^* Muharrem Dinçer,^b Alaaddin Çukurovalı ^c and Ibrahim Yılmaz ^d

^aKilis 7 Aralık University, Vocational High School of Health Services, Department of Opticianry, 79000 Kilis, Turkey, ^bOndokuz Mayıs University, Arts and Sciences Faculty, Department of Physics, 55139 Samsun, Turkey, ^cFırat University, Sciences Faculty, Department of Chemistry, 23119 Elazığ, Turkey, and ^dKaramanoğlu Mehmetbey University, Faculty of Science, Department of Chemistry, 70200 Karaman, Turkey
^*Correspondence e-mail: fatihsen55@gmail.com

(Received 24 February 2012; accepted 7 March 2012; online 14 March 2012)

The title molecule, C₂₆H₃₅NO₂, contains two cyclobutane rings that adopt butterfly conformations and are linked by a –CH(OH)CH₂NHCH₂CH(OH)– bridge. In the crystal, N—H⋯O, O—H⋯N and O—H⋯O hydrogen bonds together with C–H⋯π interactions link the molecules.

Related literature

For applications of related compounds, see: Dehmlow & Schmidt (1990 ); Coghi et al. (1976 ). For the preparation, see: Zalipsky et al. (1983 ). For puckering of the cyclobutane ring, see: Swenson et al. (1997 ); Allen (1984 ).

Experimental

Crystal data

C₂₆H₃₅NO₂
M_r = 393.55
Monoclinic, P 2₁ /c
a = 6.2156 (4) Å
b = 33.2505 (15) Å
c = 12.1792 (8) Å
β = 110.656 (5)°
V = 2355.3 (2) Å³
Z = 4
Mo Kα radiation
μ = 0.07 mm⁻¹
T = 296 K
0.63 × 0.34 × 0.09 mm

Data collection

Stoe IPDS 2 diffractometer
Absorption correction: integration (X-RED32; Stoe & Cie, 2002 ) T_min = 0.967, T_max = 0.994
26921 measured reflections
4737 independent reflections
1740 reflections with I > 2σ(I)
R_int = 0.105

Refinement

R[F² > 2σ(F²)] = 0.068
wR(F²) = 0.173
S = 0.95
4737 reflections
271 parameters
2 restraints
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.29 e Å⁻³
Δρ_min = −0.13 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

Cg1 is the centroid of the C1–C6 ring.

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1N⋯O2ⁱ	0.87 (3)	2.38 (3)	3.157 (4)	149 (3)
O1—H1O⋯N1ⁱⁱ	0.97 (2)	1.81 (3)	2.768 (4)	170 (3)
O2—H2O⋯O1)ⁱ	0.94 (3)	1.86 (3)	2.681 (4)	146 (3)
C24—H24⋯Cg1ⁱⁱⁱ	0.93	3.86 (1)	2.76	156
Symmetry codes: (i) -x+1, -y, -z; (ii) -x+2, -y, -z; (iii) $[-x+2, y-{\script{1\over 2}}, -z+{\script{1\over 2}}]$ .

Data collection: X-AREA (Stoe & Cie, 2002); cell refinement: X-AREA; data reduction: X-RED32 (Stoe & Cie, 2002); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997 ); software used to prepare material for publication: WinGX (Farrugia, 1999 ) and PLATON (Spek, 2009 ).

Supporting information

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536812010203/sj5204sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536812010203/sj5204Isup2.hkl

Supporting information file. DOI: 10.1107/S1600536812010203/sj5204Isup3.cml

checkCIF report

Comment top

It is well known that 3-substituted cyclobutane carboxylic acid derivatives exhibit anti-inflammatory and anti-depressant activity (Dehmlow & Schmidt, 1990), and also liquid crystal properties (Coghi, et al., 1976).

The structure of (I) (Fig. 1) contains two cyclobutane rings (C7—C10),(C16—C19) each with methyl and phenyl substituents in the 3-position. The four-membered rings are linked by a C12,C13,N1,C14,C15 bridge. The best fit meanplanes through the (C7—C10) and (C16—C19) atoms of the cyclobutane rings subtend dihedral angles of 36.69 (24)°, 41.91 (21)° with the planes of the (C1—C6) and (C21—C26) phenyl rings respectively.

Values for the puckering of the cyclobutane has been reported as 23.5-24.3° (Swenson et al.. 1997, Allen, 1984). In this molecule the C7—C8—C9 plane forms a dihedral angle of 25.83 (43)° with the C9—C10—C7 plane and the angle between the C16—C17—C18 and C18—C19—C16 planes is 26.74 (36)°.

In the crystal structure N—H···O, O—H···N and C—H···π interactions stabilize the packing, Table 2, and link the molecules into infinite chains, Fig.2, Fig. 3.

Related literature top

For applications of related compounds, see: Dehmlow & Schmidt (1990); Coghi et al. (1976). For the preparation, see: Zalipsky et al. (1983). For puckering of the cyclobutane ring, see: Swenson et al. (1997); Allen (1984).

Experimental top

The compound was synthesised using a literature method (Zalipsky et al., 1983) with some modification. Colourless plate-like crystals suitable for X-ray analysis were obtained by crystallization from ethanol. Overall yield: 71%. M.p.: 445 K (EtOH).

Structure description top

In the crystal structure N—H···O, O—H···N and C—H···π interactions stabilize the packing, Table 2, and link the molecules into infinite chains, Fig.2, Fig. 3.

For applications of related compounds, see: Dehmlow & Schmidt (1990); Coghi et al. (1976). For the preparation, see: Zalipsky et al. (1983). For puckering of the cyclobutane ring, see: Swenson et al. (1997); Allen (1984).

Computing details top

Data collection: X-AREA (Stoe & Cie, 2002); cell refinement: X-AREA (Stoe & Cie, 2002); data reduction: X-RED32 (Stoe & Cie, 2002); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997); software used to prepare material for publication: WinGX (Farrugia, 1999) and PLATON (Spek, 2009).

Figures top

	Fig. 1. The structure of (I), showing the atom numbering scheme. Displacement ellipsoids are drawn at the 30% probability level.
	Fig. 2. Part of the crystal structure of the title compound, showing the N—H···O and O—H···N interactions. For clarity, only H atoms involved in hydrogen bonding have been included. For symmetry codes, see Table 1.
	Fig. 3. Part of the crystal structure of the title compound, showing the C—H···π interactions.For clarity, only H atoms involved in hydrogen bonding have been included.For symmetry codes, see table 1.

1,1'-Bis(3-methyl-3-phenylcyclobutyl)-2,2'-(azanediyl)diethanol top

Crystal data top

C₂₆H₃₅NO₂	F(000) = 856
M_r = 393.55	D_x = 1.110 Mg m⁻³
Monoclinic, P2₁/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 18482 reflections
a = 6.2156 (4) Å	θ = 1.2–26.7°
b = 33.2505 (15) Å	µ = 0.07 mm⁻¹
c = 12.1792 (8) Å	T = 296 K
β = 110.656 (5)°	Plate, colourless
V = 2355.3 (2) Å³	0.63 × 0.34 × 0.09 mm
Z = 4

Data collection top

Stoe IPDS 2 diffractometer	4737 independent reflections
Radiation source: fine-focus sealed tube	1740 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.105
Detector resolution: 6.67 pixels mm^-1	θ_max = 26.3°, θ_min = 1.2°
rotation method scans	h = −7→7
Absorption correction: integration (X-RED32; Stoe & Cie, 2002)	k = −41→41
T_min = 0.967, T_max = 0.994	l = −15→15
26921 measured reflections

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)] = 0.068	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.173	H atoms treated by a mixture of independent and constrained refinement
S = 0.95	w = 1/[σ²(F_o²) + (0.0627P)²] where P = (F_o² + 2F_c²)/3
4737 reflections	(Δ/σ)_max < 0.001
271 parameters	Δρ_max = 0.29 e Å⁻³
2 restraints	Δρ_min = −0.13 e Å⁻³

Crystal data top

C₂₆H₃₅NO₂	V = 2355.3 (2) Å³
M_r = 393.55	Z = 4
Monoclinic, P2₁/c	Mo Kα radiation
a = 6.2156 (4) Å	µ = 0.07 mm⁻¹
b = 33.2505 (15) Å	T = 296 K
c = 12.1792 (8) Å	0.63 × 0.34 × 0.09 mm
β = 110.656 (5)°

Data collection top

Stoe IPDS 2 diffractometer	4737 independent reflections
Absorption correction: integration (X-RED32; Stoe & Cie, 2002)	1740 reflections with I > 2σ(I)
T_min = 0.967, T_max = 0.994	R_int = 0.105
26921 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.068	2 restraints
wR(F²) = 0.173	H atoms treated by a mixture of independent and constrained refinement
S = 0.95	Δρ_max = 0.29 e Å⁻³
4737 reflections	Δρ_min = −0.13 e Å⁻³
271 parameters

Special details top

Experimental. IR (KBr, ν cm-1): 3416 (–OH), 3288 (–NH–), 3089–3024 (aromatics), 2960–2858 (aliphatics), 1497 (C—N), 1113 (C—O), ¹H NMR (CDCl₃, TMS, δ p.p.m.): 1.46 (s, 6H,–CH₃), 2.08 (d,j = 8.8 Hz, 4H, CH₂– in cyclobutane ring), 2.21 (d, j = 8.4 Hz, 4H, –CH₂– in cyclobutane ring), 2.32–2.42 (m, 4H, CH2-), 2.59 (dd, j=12.0 Hz, 2H, >CH–), 3.15 (brs, 3H, –OH plus –NH–),3.50 (quint, j₁=7.4 Hz, j₂=2.4 Hz, 2H, >CH–, in cyclobutane), 7.13–7.20 (m, 6H, aromatics), 7.29–7.33 (m, 4H, aromatics). ¹³C NMR (CDCl₃, TMS, δ p.p.m.): 152.47, 128.20, 125.26, 124.66, 74.27, 53.20, 38.77, 36.80, 36.14, 33.15, 30.70.

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
C1	0.8359 (8)	0.20105 (13)	−0.1639 (4)	0.1058 (13)
H1	0.7569	0.2015	−0.1117	0.127*
C2	0.7425 (10)	0.21975 (15)	−0.2715 (6)	0.140 (2)
H2	0.6004	0.2324	−0.2916	0.168*
C3	0.8559 (17)	0.2198 (2)	−0.3480 (6)	0.165 (3)
H3	0.7941	0.2330	−0.4196	0.198*
C4	1.0599 (15)	0.2005 (2)	−0.3198 (6)	0.154 (2)
H4	1.1362	0.1997	−0.3731	0.184*
C5	1.1544 (9)	0.18199 (13)	−0.2128 (4)	0.1127 (15)
H5	1.2963	0.1693	−0.1942	0.135*
C6	1.0466 (8)	0.18161 (11)	−0.1327 (4)	0.0830 (11)
C7	1.1539 (6)	0.16222 (10)	−0.0146 (3)	0.0773 (10)
C8	1.2839 (6)	0.12244 (11)	−0.0088 (4)	0.0976 (12)
H8A	1.2404	0.1085	−0.0833	0.117*
H8B	1.4496	0.1251	0.0261	0.117*
C9	1.1733 (6)	0.10506 (11)	0.0749 (3)	0.0848 (11)
H9	1.2729	0.1100	0.1563	0.102*
C10	0.9910 (6)	0.13874 (10)	0.0332 (3)	0.0834 (10)
H10A	0.8492	0.1302	−0.0272	0.100*
H10B	0.9604	0.1523	0.0966	0.100*
C11	1.3001 (7)	0.19339 (12)	0.0741 (4)	0.1111 (14)
H11A	1.3692	0.1809	0.1495	0.167*
H11B	1.2038	0.2152	0.0803	0.167*
H11C	1.4183	0.2035	0.0479	0.167*
C12	1.0931 (6)	0.06167 (11)	0.0605 (3)	0.0784 (10)
H12	1.2276	0.0441	0.0781	0.094*
C13	0.9725 (6)	0.05249 (11)	0.1454 (3)	0.0858 (11)
H13A	1.0804	0.0563	0.2246	0.103*
H13B	0.8486	0.0717	0.1329	0.103*
C14	0.7920 (6)	0.00309 (10)	0.2295 (3)	0.0822 (10)
H14A	0.6836	0.0239	0.2311	0.099*
H14B	0.9194	0.0039	0.3038	0.099*
C15	0.6758 (6)	−0.03736 (10)	0.2161 (3)	0.0742 (10)
H15	0.7914	−0.0581	0.2221	0.089*
C16	0.5795 (5)	−0.04484 (10)	0.3104 (3)	0.0694 (9)
H16	0.4640	−0.0244	0.3076	0.083*
C17	0.7514 (5)	−0.04950 (9)	0.4367 (3)	0.0697 (9)
H17A	0.9025	−0.0585	0.4407	0.084*
H17B	0.7628	−0.0258	0.4849	0.084*
C18	0.6036 (5)	−0.08305 (9)	0.4600 (3)	0.0644 (9)
C19	0.4902 (6)	−0.08705 (11)	0.3251 (3)	0.0842 (11)
H19A	0.5548	−0.1084	0.2922	0.101*
H19B	0.3239	−0.0889	0.2977	0.101*
C20	0.4371 (6)	−0.06601 (13)	0.5146 (4)	0.1093 (14)
H20A	0.3630	−0.0426	0.4716	0.164*
H20B	0.5200	−0.0588	0.5947	0.164*
H20C	0.3233	−0.0859	0.5117	0.164*
C21	0.7205 (7)	−0.11958 (11)	0.5263 (3)	0.0751 (10)
C22	0.9511 (7)	−0.11942 (13)	0.5945 (3)	0.0999 (13)
H22	1.0387	−0.0963	0.6001	0.120*
C23	1.0512 (11)	−0.1540 (2)	0.6546 (5)	0.157 (3)
H23	1.2071	−0.1538	0.6996	0.189*
C24	0.9279 (19)	−0.1881 (2)	0.6496 (6)	0.183 (4)
H24	0.9979	−0.2111	0.6898	0.220*
C25	0.6985 (17)	−0.18775 (16)	0.5840 (6)	0.176 (3)
H25	0.6107	−0.2106	0.5813	0.211*
C26	0.5959 (9)	−0.15427 (13)	0.5223 (4)	0.1241 (16)
H26	0.4402	−0.1549	0.4771	0.149*
O1	0.9385 (4)	0.05398 (7)	−0.0596 (2)	0.0841 (7)
O2	0.5073 (4)	−0.03918 (9)	0.1009 (2)	0.1019 (9)
N1	0.8774 (5)	0.01166 (9)	0.1352 (2)	0.0789 (9)
H1N	0.761 (6)	0.0091 (10)	0.070 (3)	0.095*
H1O	0.986 (6)	0.0304 (9)	−0.092 (3)	0.118*
H2O	0.371 (5)	−0.0403 (12)	0.117 (3)	0.118*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
C1	0.107 (3)	0.084 (3)	0.123 (4)	−0.010 (3)	0.037 (3)	0.009 (3)
C2	0.137 (5)	0.099 (4)	0.146 (5)	−0.023 (3)	0.001 (4)	0.037 (4)
C3	0.227 (9)	0.115 (5)	0.110 (5)	−0.072 (5)	0.006 (6)	0.025 (4)
C4	0.230 (8)	0.134 (5)	0.105 (5)	−0.055 (5)	0.069 (5)	−0.001 (4)
C5	0.148 (4)	0.100 (3)	0.105 (4)	−0.019 (3)	0.064 (4)	0.001 (3)
C6	0.099 (3)	0.063 (2)	0.092 (3)	−0.022 (2)	0.041 (3)	−0.010 (2)
C7	0.079 (2)	0.067 (2)	0.090 (3)	−0.019 (2)	0.035 (2)	−0.009 (2)
C8	0.083 (2)	0.082 (3)	0.139 (4)	−0.001 (2)	0.053 (3)	0.010 (2)
C9	0.075 (2)	0.081 (3)	0.090 (3)	−0.013 (2)	0.019 (2)	0.007 (2)
C10	0.084 (2)	0.081 (2)	0.091 (3)	0.000 (2)	0.038 (2)	0.000 (2)
C11	0.117 (3)	0.099 (3)	0.105 (3)	−0.027 (3)	0.026 (3)	−0.011 (3)
C12	0.069 (2)	0.085 (3)	0.071 (2)	−0.0025 (19)	0.012 (2)	0.011 (2)
C13	0.092 (2)	0.079 (3)	0.078 (2)	−0.010 (2)	0.020 (2)	0.011 (2)
C14	0.093 (3)	0.080 (3)	0.065 (2)	−0.006 (2)	0.018 (2)	0.0078 (19)
C15	0.073 (2)	0.081 (3)	0.055 (2)	−0.0028 (19)	0.0054 (19)	0.0093 (18)
C16	0.0628 (19)	0.069 (2)	0.071 (2)	0.0057 (17)	0.0173 (18)	0.0129 (18)
C17	0.071 (2)	0.072 (2)	0.061 (2)	−0.0004 (17)	0.0162 (18)	0.0022 (17)
C18	0.0564 (19)	0.070 (2)	0.068 (2)	0.0012 (17)	0.0227 (17)	0.0045 (18)
C19	0.075 (2)	0.090 (3)	0.073 (2)	−0.0131 (19)	0.0066 (19)	0.007 (2)
C20	0.093 (3)	0.119 (3)	0.131 (4)	0.022 (2)	0.060 (3)	0.025 (3)
C21	0.096 (3)	0.069 (2)	0.063 (2)	0.011 (2)	0.031 (2)	0.0043 (18)
C22	0.097 (3)	0.122 (3)	0.084 (3)	0.038 (3)	0.036 (2)	0.034 (3)
C23	0.173 (5)	0.194 (7)	0.118 (4)	0.101 (6)	0.068 (4)	0.074 (5)
C24	0.317 (12)	0.146 (6)	0.104 (5)	0.133 (8)	0.096 (6)	0.065 (5)
C25	0.327 (10)	0.069 (4)	0.123 (5)	0.001 (5)	0.069 (6)	0.023 (3)
C26	0.172 (4)	0.077 (3)	0.107 (3)	−0.017 (3)	0.030 (3)	0.012 (3)
O1	0.0786 (15)	0.0864 (17)	0.0791 (17)	0.0006 (13)	0.0177 (13)	0.0055 (14)
O2	0.0920 (18)	0.128 (2)	0.0659 (16)	−0.0200 (17)	0.0035 (15)	0.0200 (15)
N1	0.090 (2)	0.084 (2)	0.0557 (18)	−0.0114 (18)	0.0164 (15)	0.0083 (16)

Geometric parameters (Å, º) top

C1—C2	1.381 (6)	C14—H14A	0.9700
C1—C6	1.388 (5)	C14—H14B	0.9700
C1—H1	0.9300	C15—O2	1.426 (3)
C2—C3	1.352 (9)	C15—C16	1.491 (4)
C2—H2	0.9300	C15—H15	0.9800
C3—C4	1.353 (8)	C16—C17	1.540 (4)
C3—H3	0.9300	C16—C19	1.543 (4)
C4—C5	1.372 (7)	C16—H16	0.9800
C4—H4	0.9300	C17—C18	1.534 (4)
C5—C6	1.365 (5)	C17—H17A	0.9700
C5—H5	0.9300	C17—H17B	0.9700
C6—C7	1.500 (5)	C18—C21	1.497 (4)
C7—C8	1.538 (5)	C18—C20	1.523 (4)
C7—C11	1.541 (4)	C18—C19	1.548 (4)
C7—C10	1.546 (4)	C19—H19A	0.9700
C8—C9	1.529 (5)	C19—H19B	0.9700
C8—H8A	0.9700	C20—H20A	0.9600
C8—H8B	0.9700	C20—H20B	0.9600
C9—C12	1.516 (5)	C20—H20C	0.9600
C9—C10	1.546 (4)	C21—C22	1.380 (4)
C9—H9	0.9800	C21—C26	1.380 (5)
C10—H10A	0.9700	C22—C23	1.387 (6)
C10—H10B	0.9700	C22—H22	0.9300
C11—H11A	0.9600	C23—C24	1.358 (9)
C11—H11B	0.9600	C23—H23	0.9300
C11—H11C	0.9600	C24—C25	1.367 (9)
C12—O1	1.462 (4)	C24—H24	0.9300
C12—C13	1.506 (5)	C25—C26	1.368 (7)
C12—H12	0.9800	C25—H25	0.9300
C13—N1	1.469 (4)	C26—H26	0.9300
C13—H13A	0.9700	O1—H1O	0.97 (2)
C13—H13B	0.9700	O2—H2O	0.93 (2)
C14—N1	1.453 (4)	N1—H1N	0.87 (3)
C14—C15	1.508 (4)

C2—C1—C6	120.6 (5)	N1—C14—H14B	109.1
C2—C1—H1	119.7	C15—C14—H14B	109.1
C6—C1—H1	119.7	H14A—C14—H14B	107.8
C3—C2—C1	120.6 (7)	O2—C15—C16	113.3 (3)
C3—C2—H2	119.7	O2—C15—C14	107.6 (3)
C1—C2—H2	119.7	C16—C15—C14	111.9 (3)
C2—C3—C4	119.6 (8)	O2—C15—H15	108.0
C2—C3—H3	120.2	C16—C15—H15	108.0
C4—C3—H3	120.2	C14—C15—H15	108.0
C3—C4—C5	120.2 (7)	C15—C16—C17	117.4 (3)
C3—C4—H4	119.9	C15—C16—C19	120.0 (3)
C5—C4—H4	119.9	C17—C16—C19	86.8 (2)
C6—C5—C4	122.0 (5)	C15—C16—H16	110.2
C6—C5—H5	119.0	C17—C16—H16	110.2
C4—C5—H5	119.0	C19—C16—H16	110.2
C5—C6—C1	117.0 (4)	C18—C17—C16	90.5 (2)
C5—C6—C7	121.7 (4)	C18—C17—H17A	113.6
C1—C6—C7	121.3 (4)	C16—C17—H17A	113.6
C6—C7—C8	117.5 (3)	C18—C17—H17B	113.6
C6—C7—C11	109.6 (3)	C16—C17—H17B	113.6
C8—C7—C11	112.1 (3)	H17A—C17—H17B	110.8
C6—C7—C10	116.7 (3)	C21—C18—C20	110.0 (3)
C8—C7—C10	87.2 (3)	C21—C18—C17	118.8 (3)
C11—C7—C10	112.2 (3)	C20—C18—C17	110.7 (3)
C9—C8—C7	90.2 (3)	C21—C18—C19	117.1 (3)
C9—C8—H8A	113.6	C20—C18—C19	111.7 (3)
C7—C8—H8A	113.6	C17—C18—C19	86.8 (2)
C9—C8—H8B	113.6	C16—C19—C18	89.9 (2)
C7—C8—H8B	113.6	C16—C19—H19A	113.7
H8A—C8—H8B	110.9	C18—C19—H19A	113.7
C12—C9—C8	119.3 (3)	C16—C19—H19B	113.7
C12—C9—C10	118.6 (3)	C18—C19—H19B	113.7
C8—C9—C10	87.5 (3)	H19A—C19—H19B	110.9
C12—C9—H9	109.9	C18—C20—H20A	109.5
C8—C9—H9	109.9	C18—C20—H20B	109.5
C10—C9—H9	109.9	H20A—C20—H20B	109.5
C7—C10—C9	89.3 (3)	C18—C20—H20C	109.5
C7—C10—H10A	113.8	H20A—C20—H20C	109.5
C9—C10—H10A	113.8	H20B—C20—H20C	109.5
C7—C10—H10B	113.8	C22—C21—C26	118.4 (4)
C9—C10—H10B	113.8	C22—C21—C18	121.7 (3)
H10A—C10—H10B	111.0	C26—C21—C18	120.0 (4)
C7—C11—H11A	109.5	C21—C22—C23	119.5 (5)
C7—C11—H11B	109.5	C21—C22—H22	120.3
H11A—C11—H11B	109.5	C23—C22—H22	120.3
C7—C11—H11C	109.5	C24—C23—C22	121.9 (7)
H11A—C11—H11C	109.5	C24—C23—H23	119.1
H11B—C11—H11C	109.5	C22—C23—H23	119.1
O1—C12—C13	109.9 (3)	C23—C24—C25	118.3 (6)
O1—C12—C9	110.8 (3)	C23—C24—H24	120.8
C13—C12—C9	109.7 (3)	C25—C24—H24	120.8
O1—C12—H12	108.8	C24—C25—C26	121.1 (7)
C13—C12—H12	108.8	C24—C25—H25	119.5
C9—C12—H12	108.8	C26—C25—H25	119.5
N1—C13—C12	114.4 (3)	C25—C26—C21	120.9 (5)
N1—C13—H13A	108.7	C25—C26—H26	119.5
C12—C13—H13A	108.7	C21—C26—H26	119.5
N1—C13—H13B	108.7	C12—O1—H1O	111 (2)
C12—C13—H13B	108.7	C15—O2—H2O	102 (2)
H13A—C13—H13B	107.6	C14—N1—C13	111.3 (3)
N1—C14—C15	112.6 (3)	C14—N1—H1N	106 (2)
N1—C14—H14A	109.1	C13—N1—H1N	110 (2)
C15—C14—H14A	109.1

C6—C1—C2—C3	−0.7 (7)	N1—C14—C15—C16	−177.3 (3)
C1—C2—C3—C4	1.7 (9)	O2—C15—C16—C17	171.5 (3)
C2—C3—C4—C5	−2.0 (10)	C14—C15—C16—C17	−66.6 (4)
C3—C4—C5—C6	1.3 (8)	O2—C15—C16—C19	68.5 (4)
C4—C5—C6—C1	−0.3 (6)	C14—C15—C16—C19	−169.7 (3)
C4—C5—C6—C7	−178.4 (4)	C15—C16—C17—C18	−140.9 (3)
C2—C1—C6—C5	0.0 (6)	C19—C16—C17—C18	−18.6 (3)
C2—C1—C6—C7	178.1 (4)	C16—C17—C18—C21	137.9 (3)
C5—C6—C7—C8	−39.3 (5)	C16—C17—C18—C20	−93.5 (3)
C1—C6—C7—C8	142.6 (3)	C16—C17—C18—C19	18.6 (2)
C5—C6—C7—C11	90.2 (4)	C15—C16—C19—C18	138.4 (3)
C1—C6—C7—C11	−87.9 (4)	C17—C16—C19—C18	18.5 (2)
C5—C6—C7—C10	−140.9 (4)	C21—C18—C19—C16	−139.4 (3)
C1—C6—C7—C10	41.1 (5)	C20—C18—C19—C16	92.5 (3)
C6—C7—C8—C9	−136.8 (3)	C17—C18—C19—C16	−18.5 (2)
C11—C7—C8—C9	94.8 (3)	C20—C18—C21—C22	−110.3 (4)
C10—C7—C8—C9	−18.1 (3)	C17—C18—C21—C22	18.7 (5)
C7—C8—C9—C12	139.7 (3)	C19—C18—C21—C22	120.7 (3)
C7—C8—C9—C10	18.1 (3)	C20—C18—C21—C26	68.1 (4)
C6—C7—C10—C9	137.4 (3)	C17—C18—C21—C26	−162.9 (4)
C8—C7—C10—C9	17.9 (3)	C19—C18—C21—C26	−60.8 (4)
C11—C7—C10—C9	−94.9 (3)	C26—C21—C22—C23	1.3 (6)
C12—C9—C10—C7	−140.3 (4)	C18—C21—C22—C23	179.7 (4)
C8—C9—C10—C7	−18.0 (3)	C21—C22—C23—C24	−0.8 (8)
C8—C9—C12—O1	−53.6 (4)	C22—C23—C24—C25	−0.6 (11)
C10—C9—C12—O1	50.8 (5)	C23—C24—C25—C26	1.7 (11)
C8—C9—C12—C13	−175.1 (3)	C24—C25—C26—C21	−1.2 (9)
C10—C9—C12—C13	−70.7 (4)	C22—C21—C26—C25	−0.3 (7)
O1—C12—C13—N1	55.1 (4)	C18—C21—C26—C25	−178.8 (4)
C9—C12—C13—N1	177.2 (3)	C15—C14—N1—C13	175.4 (3)
N1—C14—C15—O2	−52.2 (4)	C12—C13—N1—C14	172.2 (3)

Hydrogen-bond geometry (Å, º) top

Cg1 is the centroid of the C1–C6 ring.

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1N···O2ⁱ	0.87 (3)	2.38 (3)	3.157 (4)	149 (3)
O1—H1O···N1ⁱⁱ	0.97 (2)	1.81 (3)	2.768 (4)	170 (3)
O2—H2O···O1)ⁱ	0.94 (3)	1.86 (3)	2.681 (4)	146 (3)
C24—H24···Cg1ⁱⁱⁱ	0.93	3.86 (1)	2.76	156

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

Experimental details

Crystal data
Chemical formula	C₂₆H₃₅NO₂
M_r	393.55
Crystal system, space group	Monoclinic, P2₁/c
Temperature (K)	296
a, b, c (Å)	6.2156 (4), 33.2505 (15), 12.1792 (8)
β (°)	110.656 (5)
V (Å³)	2355.3 (2)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.07
Crystal size (mm)	0.63 × 0.34 × 0.09

Data collection
Diffractometer	Stoe IPDS 2
Absorption correction	Integration (X-RED32; Stoe & Cie, 2002)
T_min, T_max	0.967, 0.994
No. of measured, independent and observed [I > 2σ(I)] reflections	26921, 4737, 1740
R_int	0.105
(sin θ/λ)_max (Å⁻¹)	0.623

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.068, 0.173, 0.95
No. of reflections	4737
No. of parameters	271
No. of restraints	2
H-atom treatment	H atoms treated by a mixture of independent and constrained refinement
Δρ_max, Δρ_min (e Å⁻³)	0.29, −0.13

Computer programs: X-AREA (Stoe & Cie, 2002), X-RED32 (Stoe & Cie, 2002), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), ORTEP-3 for Windows (Farrugia, 1997), WinGX (Farrugia, 1999) and PLATON (Spek, 2009).

Hydrogen-bond geometry (Å, º) top

Cg1 is the centroid of the C1–C6 ring.

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1N···O2ⁱ	0.87 (3)	2.38 (3)	3.157 (4)	149 (3)
O1—H1O···N1ⁱⁱ	0.97 (2)	1.81 (3)	2.768 (4)	170 (3)
O2—H2O···O1)ⁱ	0.94 (3)	1.86 (3)	2.681 (4)	146 (3)
C24—H24···Cg1ⁱⁱⁱ	0.93	3.858 (7)	2.76	156

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

References

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Farrugia, L. J. (1997). J. Appl. Cryst. 30, 565. CrossRef IUCr Journals Google Scholar
Farrugia, L. J. (1999). J. Appl. Cryst. 32, 837–838. CrossRef CAS IUCr Journals Google Scholar
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Volume 68| Part 4| April 2012| Page o1052

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