2-((E)-{4-[Bis(4-eth­oxy­phen­yl)amino]­phen­yl}imino­meth­yl)phenol

Gao, B.-F.; Jin, Z.-P.; Chen, J.; Tian, Y.-P.

doi:10.1107/S1600536814003201

organic compounds

CRYSTALLOGRAPHIC
COMMUNICATIONS

ISSN: 2056-9890

Volume 70| Part 3| March 2014| Page o313

doi:10.1107/S1600536814003201

Open

access

2-((E)-{4-[Bis(4-ethoxyphenyl)amino]phenyl}iminomethyl)phenol

Bing-Fei Gao,^a,^b Zhe-Peng Jin,^a,^b Jiang Chen ^c and Yu-Peng Tian ^a,^b ^*

^aDepartment of Chemistry, Anhui University, Hefei 230039, People's Republic of China, ^bKey Laboratory of Functional Inorganic Materials Chemistry, Hefei 230039, People's Republic of China, and ^cDepartment of Chemistry, Bengbu Medical College, Bengbu 233030, People's Republic of China
^*Correspondence e-mail: yptian@ahu.edu.cn

(Received 16 January 2014; accepted 12 February 2014; online 15 February 2014)

In the title Schiff base molecule, C₂₉H₂₈N₂O₃, the three terminal benzene rings are twisted by 73.84 (15), 81.25 (16) and 12.1 (2)° with respect to the central benzene ring. An intramolecular O—H⋯N hydrogen bond occurs. In the crystal, molecules are linked via weak C—H⋯π interactions into a three-dimensional supramolecular architecture.

CCDC reference: 986499

Related literature

For background and the synthesis of the title compound, see: Dharmaraj et al. (2001 ); Feng (2014 ). For a related structure, see: Tanak et al. (2013 ).

Experimental

Crystal data

C₂₉H₂₈N₂O₃
M_r = 452.53
Orthorhombic, P 2₁ 2₁ 2₁
a = 9.765 (3) Å
b = 13.113 (4) Å
c = 19.378 (6) Å
V = 2481.2 (14) Å³
Z = 4
Mo Kα radiation
μ = 0.08 mm⁻¹
T = 296 K
0.40 × 0.30 × 0.20 mm

Data collection

Bruker SMART CCD area-detector diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2001 ) T_min = 0.969, T_max = 0.984
17684 measured reflections
2486 independent reflections
1747 reflections with I > 2σ(I)
R_int = 0.051

Refinement

R[F² > 2σ(F²)] = 0.044
wR(F²) = 0.113
S = 1.13
2486 reflections
310 parameters
6 restraints
H-atom parameters constrained
Δρ_max = 0.12 e Å⁻³
Δρ_min = −0.18 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

Cg1 Cg2 and Cg3 are the centroids of the C3–C8, C11–C16 and C17–C22 benzene rings, respectively.

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O3—H3⋯N2	0.82	1.87	2.605 (4)	148
C1—H1C⋯Cg2ⁱ	0.96	2.84	3.760 (4)	162
C4—H4⋯Cg3ⁱⁱ	0.93	2.82	3.655 (3)	150
C9—H9C⋯Cg1ⁱⁱⁱ	0.96	2.94	3.872 (4)	164
C28—H28⋯Cg1^iv	0.93	2.88	3.742 (4)	154
Symmetry codes: (i) $[-x, y+{\script{1\over 2}}, -z+{\script{5\over 2}}]$ ; (ii) $[x+{\script{1\over 2}}, -y+{\script{1\over 2}}, -z+2]$ ; (iii) $[-x, y-{\script{1\over 2}}, -z+{\script{5\over 2}}]$ ; (iv) $[-x, y-{\script{1\over 2}}, -z+{\script{3\over 2}}]$ .

Data collection: SMART (Bruker, 2007 ); cell refinement: SAINT (Bruker, 2007); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXTL.

Supporting information

CCDC reference: 986499

Crystal structure: contains datablocks I, Global. DOI: 10.1107/S1600536814003201/xu5765sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536814003201/xu5765Isup2.hkl

Supporting information file. DOI: 10.1107/S1600536814003201/xu5765Isup3.cml

checkCIF report

Comment top

In the past few decades, the researchers have witnessed a great deal of interest in the chemistry of transition metal Schiff base chelates bacause of their importance as catalysts in reactions such as carbonylation, hydroformylation, reduction, oxidation, epoxidation and hydrolysis (Dharmaraj et al., 2001). Schiff bases derived from salicyladehyde and fluoroaniline, specifically, have been considered as potential pharmaceutically interesting compounds as several of the members of this family of molecules have shown antimicrobial, antitumor or antiviral activities (Feng et al., 2014). As an extension of our work on the structural characterization of Schiff base compounds, the crystal structure of the title compound (I) is reported.

In (I) (Fig.1), the molecular structure of title compound shows an E configuration, with a C(20)—N(2)=C(23)—C(24) torsion angle of -176.9 (3)°. The bond distance of N(2)=C(23) at 1.258 (3) Å is a typical double bond. The dihedral angles between the salicyladehyde moiety and the aniline ring is 12.1 (2)°, indicating they are nearly coplanar. Intramolecular O—H···N hydrogen bond exists, similar to that found in a related structure (Tanak et al. 2013). In the crystal, the molecules are linked via weak C—H···π interaction into the three dimensional supramolecular architecture.

Related literature top

For background and the synthesis of the title compound, see: Dharmaraj et al. (2001); Feng (2014). For a related structure, see: Tanak et al. (2013).

Experimental top

A hot solution of N¹,N¹ -bis (4-ethoxyphenyl) benzene -1,4 - diamine (3.48 g, 10 mmol) in ethanol 50 mL was mixed with a salicylaldehyde (1.83 g, 15 mmol) in ethanol 5 mL, a yellow solid was appeared immediately, then the reaction mixture was reflux for 2 h. Under cooling the room temperature, the light yellow crystals were separated by filtration and recrystallized from ethanol. Yield: 96%. ¹H NMR (400 MHz, DMSO-d⁶) 1.34 (t, 6H), 4.03 (m, 4H), 6.82 (d, 2H), 6.97 (m, 6H), 7.04 (d, 4H), 7.31 (d, 2H), 7.38 (t, 1H), 7.59 (d, 1H), 8.90 (s, 1H), 13.37 (s, 1H).

Computing details top

Data collection: SMART (Bruker, 2007); cell refinement: SAINT (Bruker, 2007); data reduction: SAINT (Bruker, 2007); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXTL (Sheldrick, 2008).

Figures top

	Fig. 1. : The molecular structure of (I), with the atom-numbering scheme. Displacement ellipsoids are drawn at the 30% probability level.
	Fig. 2. : The H-bond diagram of the title molecule(I).

2-((E)-{4-[Bis(4-ethoxyphenyl)amino]phenyl}iminomethyl)phenol top

Crystal data top

C₂₉H₂₈N₂O₃	D_x = 1.211 Mg m⁻³
M_r = 452.53	Mo Kα radiation, λ = 0.71073 Å
Orthorhombic, P2₁2₁2₁	Cell parameters from 2336 reflections
a = 9.765 (3) Å	θ = 2.3–20.7°
b = 13.113 (4) Å	µ = 0.08 mm⁻¹
c = 19.378 (6) Å	T = 296 K
V = 2481.2 (14) Å³	Block, yellow
Z = 4	0.40 × 0.30 × 0.20 mm
F(000) = 960

Data collection top

Bruker SMART CCD area-detector diffractometer	2486 independent reflections
Radiation source: fine-focus sealed tube	1747 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.051
phi and ω scans	θ_max = 25.0°, θ_min = 1.9°
Absorption correction: multi-scan (SADABS; Bruker, 2001)	h = −11→11
T_min = 0.969, T_max = 0.984	k = −15→15
17684 measured reflections	l = −22→22

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)] = 0.044	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.113	H-atom parameters constrained
S = 1.13	w = 1/[σ²(F_o²) + (0.0561P)²] where P = (F_o² + 2F_c²)/3
2486 reflections	(Δ/σ)_max < 0.001
310 parameters	Δρ_max = 0.12 e Å⁻³
6 restraints	Δρ_min = −0.18 e Å⁻³

Crystal data top

C₂₉H₂₈N₂O₃	V = 2481.2 (14) Å³
M_r = 452.53	Z = 4
Orthorhombic, P2₁2₁2₁	Mo Kα radiation
a = 9.765 (3) Å	µ = 0.08 mm⁻¹
b = 13.113 (4) Å	T = 296 K
c = 19.378 (6) Å	0.40 × 0.30 × 0.20 mm

Data collection top

Bruker SMART CCD area-detector diffractometer	2486 independent reflections
Absorption correction: multi-scan (SADABS; Bruker, 2001)	1747 reflections with I > 2σ(I)
T_min = 0.969, T_max = 0.984	R_int = 0.051
17684 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.044	6 restraints
wR(F²) = 0.113	H-atom parameters constrained
S = 1.13	Δρ_max = 0.12 e Å⁻³
2486 reflections	Δρ_min = −0.18 e Å⁻³
310 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 > 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	0.1807 (5)	0.6157 (3)	1.2427 (2)	0.0891 (13)
H1A	0.1266	0.6695	1.2231	0.134*
H1B	0.2698	0.6414	1.2543	0.134*
H1C	0.1367	0.5904	1.2835	0.134*
C2	0.1945 (4)	0.5321 (3)	1.1919 (2)	0.0741 (11)
H2A	0.2332	0.5582	1.1493	0.089*
H2B	0.2555	0.4800	1.2098	0.089*
C3	0.0558 (3)	0.4027 (2)	1.13890 (15)	0.0476 (8)
C4	0.1641 (3)	0.3628 (2)	1.10191 (16)	0.0554 (9)
H4	0.2488	0.3953	1.1023	0.066*
C5	0.1461 (3)	0.2750 (3)	1.06451 (17)	0.0569 (9)
H5	0.2196	0.2478	1.0402	0.068*
C6	0.0203 (3)	0.2259 (2)	1.06227 (15)	0.0484 (8)
C7	−0.0875 (3)	0.2676 (3)	1.09885 (16)	0.0560 (9)
H7	−0.1727	0.2361	1.0976	0.067*
C8	−0.0708 (4)	0.3548 (2)	1.13691 (16)	0.0551 (9)
H8	−0.1442	0.3819	1.1614	0.066*
C9	−0.2070 (4)	−0.3382 (3)	1.25128 (19)	0.0800 (12)
H9A	−0.1536	−0.3916	1.2306	0.120*
H9B	−0.2961	−0.3639	1.2629	0.120*
H9C	−0.1621	−0.3145	1.2923	0.120*
C10	−0.2213 (4)	−0.2511 (3)	1.2010 (2)	0.0757 (11)
H10A	−0.2586	−0.2754	1.1576	0.091*
H10B	−0.2823	−0.1995	1.2195	0.091*
C11	−0.0768 (4)	−0.1254 (2)	1.14919 (16)	0.0546 (8)
C12	0.0506 (4)	−0.0825 (3)	1.14815 (18)	0.0648 (10)
H12	0.1200	−0.1098	1.1753	0.078*
C13	0.0772 (4)	0.0010 (3)	1.10721 (17)	0.0584 (9)
H13	0.1647	0.0290	1.1063	0.070*
C14	−0.0254 (4)	0.0431 (2)	1.06752 (16)	0.0513 (8)
C15	−0.1533 (4)	0.0009 (3)	1.06924 (18)	0.0613 (9)
H15	−0.2233	0.0293	1.0430	0.074*
C16	−0.1797 (3)	−0.0843 (3)	1.11010 (18)	0.0631 (10)
H16	−0.2667	−0.1132	1.1108	0.076*
C17	0.0234 (3)	0.1219 (2)	0.95562 (15)	0.0486 (8)
C18	0.0227 (3)	0.2085 (2)	0.91266 (15)	0.0494 (8)
H18	0.0144	0.2732	0.9318	0.059*
C19	0.0345 (3)	0.1973 (2)	0.84202 (16)	0.0524 (8)
H19	0.0340	0.2552	0.8142	0.063*
C20	0.0470 (3)	0.1022 (2)	0.81143 (15)	0.0483 (8)
C21	0.0489 (4)	0.0180 (2)	0.85418 (17)	0.0556 (9)
H21	0.0576	−0.0465	0.8348	0.067*
C22	0.0384 (4)	0.0268 (2)	0.92461 (16)	0.0562 (9)
H22	0.0413	−0.0314	0.9519	0.067*
N2	0.0527 (3)	0.0833 (2)	0.73886 (13)	0.0539 (7)
C24	0.0683 (4)	0.1357 (3)	0.62156 (17)	0.0636 (9)
C25	0.0822 (7)	0.2158 (4)	0.5769 (2)	0.129 (2)
H25	0.0939	0.2812	0.5944	0.154*
C26	0.0793 (8)	0.2014 (4)	0.5064 (2)	0.146 (2)
H26	0.0878	0.2568	0.4767	0.175*
C27	0.0637 (7)	0.1046 (4)	0.4803 (2)	0.125 (2)
H27	0.0633	0.0945	0.4328	0.150*
C28	0.0490 (5)	0.0243 (3)	0.52299 (19)	0.0818 (12)
H28	0.0381	−0.0409	0.5050	0.098*
C29	0.0503 (4)	0.0392 (3)	0.59391 (17)	0.0615 (9)
N1	0.0028 (3)	0.13169 (19)	1.02609 (13)	0.0572 (8)
C23	0.0688 (4)	0.1534 (3)	0.69541 (17)	0.0633 (9)
H23	0.0816	0.2197	0.7113	0.076*
O1	−0.0896 (3)	−0.21002 (19)	1.19072 (13)	0.0745 (7)
O2	0.0625 (2)	0.48898 (16)	1.17876 (11)	0.0613 (6)
O3	0.0333 (4)	−0.04181 (18)	0.63487 (13)	0.0933 (10)
H3	0.0383	−0.0239	0.6753	0.140*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
C1	0.095 (3)	0.078 (3)	0.093 (3)	−0.022 (2)	0.003 (3)	−0.023 (3)
C2	0.069 (3)	0.069 (2)	0.085 (3)	−0.015 (2)	0.005 (2)	−0.012 (2)
C3	0.053 (2)	0.0494 (19)	0.0401 (17)	0.0010 (16)	0.0005 (15)	−0.0007 (15)
C4	0.0502 (18)	0.062 (2)	0.054 (2)	−0.0089 (17)	0.0027 (17)	−0.0064 (19)
C5	0.053 (2)	0.065 (2)	0.0527 (19)	−0.0001 (18)	0.0150 (17)	−0.0058 (18)
C6	0.058 (2)	0.0510 (19)	0.0365 (16)	−0.0029 (17)	0.0009 (15)	0.0031 (15)
C7	0.0462 (19)	0.067 (2)	0.0550 (19)	−0.0081 (17)	0.0033 (16)	0.0012 (19)
C8	0.049 (2)	0.064 (2)	0.052 (2)	0.0052 (17)	0.0050 (16)	−0.0077 (18)
C9	0.097 (3)	0.072 (3)	0.071 (2)	−0.023 (2)	0.002 (2)	0.014 (2)
C10	0.073 (3)	0.072 (2)	0.082 (3)	−0.010 (2)	0.002 (2)	0.008 (2)
C11	0.068 (2)	0.0469 (19)	0.0492 (18)	0.0013 (18)	0.0059 (18)	0.0055 (17)
C12	0.061 (2)	0.067 (2)	0.067 (2)	0.002 (2)	−0.0060 (19)	0.012 (2)
C13	0.054 (2)	0.061 (2)	0.060 (2)	−0.0035 (17)	0.0025 (18)	0.0040 (19)
C14	0.060 (2)	0.0538 (19)	0.0398 (17)	−0.0022 (17)	0.0059 (16)	−0.0005 (16)
C15	0.063 (2)	0.059 (2)	0.062 (2)	−0.0035 (19)	−0.0084 (18)	0.0085 (19)
C16	0.053 (2)	0.063 (2)	0.073 (2)	−0.0079 (18)	0.000 (2)	0.007 (2)
C17	0.0502 (19)	0.056 (2)	0.0397 (17)	−0.0035 (17)	0.0018 (14)	−0.0008 (16)
C18	0.054 (2)	0.0496 (18)	0.0443 (18)	−0.0055 (16)	−0.0008 (15)	−0.0019 (15)
C19	0.055 (2)	0.0566 (19)	0.0460 (18)	−0.0032 (17)	0.0010 (17)	0.0040 (16)
C20	0.0463 (19)	0.059 (2)	0.0395 (16)	0.0027 (17)	−0.0015 (15)	−0.0018 (16)
C21	0.070 (2)	0.0464 (18)	0.0508 (19)	0.0026 (18)	0.0012 (18)	−0.0051 (16)
C22	0.072 (2)	0.0481 (19)	0.0479 (19)	0.0053 (18)	0.0019 (18)	0.0021 (16)
N2	0.0578 (17)	0.0597 (17)	0.0440 (15)	0.0038 (14)	0.0024 (14)	0.0000 (15)
C24	0.081 (2)	0.065 (2)	0.0452 (19)	−0.015 (2)	0.0012 (19)	0.0000 (19)
C25	0.233 (7)	0.091 (3)	0.061 (3)	−0.055 (4)	0.010 (4)	0.006 (3)
C26	0.259 (7)	0.115 (4)	0.063 (3)	−0.054 (4)	0.009 (4)	0.019 (3)
C27	0.208 (6)	0.123 (4)	0.044 (2)	−0.050 (4)	0.001 (3)	−0.006 (3)
C28	0.112 (3)	0.083 (3)	0.051 (2)	−0.011 (3)	−0.009 (2)	−0.007 (2)
C29	0.067 (2)	0.067 (2)	0.051 (2)	0.001 (2)	−0.0048 (19)	0.002 (2)
N1	0.085 (2)	0.0491 (16)	0.0381 (14)	−0.0123 (15)	0.0043 (14)	−0.0009 (13)
C23	0.076 (2)	0.060 (2)	0.053 (2)	−0.014 (2)	0.005 (2)	−0.0069 (19)
O1	0.0706 (17)	0.0684 (15)	0.0846 (17)	−0.0048 (14)	0.0022 (14)	0.0202 (14)
O2	0.0602 (15)	0.0605 (14)	0.0630 (15)	−0.0050 (12)	0.0041 (12)	−0.0160 (12)
O3	0.159 (3)	0.0601 (16)	0.0610 (16)	0.0017 (19)	−0.008 (2)	−0.0043 (14)

Geometric parameters (Å, º) top

C1—C2	1.479 (5)	C14—C15	1.367 (5)
C1—H1A	0.9600	C14—N1	1.439 (4)
C1—H1B	0.9600	C15—C16	1.394 (4)
C1—H1C	0.9600	C15—H15	0.9300
C2—O2	1.431 (4)	C16—H16	0.9300
C2—H2A	0.9700	C17—N1	1.386 (4)
C2—H2B	0.9700	C17—C22	1.392 (4)
C3—O2	1.371 (3)	C17—C18	1.407 (4)
C3—C4	1.380 (4)	C18—C19	1.381 (4)
C3—C8	1.387 (5)	C18—H18	0.9300
C4—C5	1.372 (4)	C19—C20	1.387 (4)
C4—H4	0.9300	C19—H19	0.9300
C5—C6	1.388 (4)	C20—C21	1.380 (4)
C5—H5	0.9300	C20—N2	1.429 (4)
C6—C7	1.382 (4)	C21—C22	1.373 (4)
C6—N1	1.431 (4)	C21—H21	0.9300
C7—C8	1.370 (4)	C22—H22	0.9300
C7—H7	0.9300	N2—C23	1.257 (4)
C8—H8	0.9300	C24—C25	1.368 (5)
C9—C10	1.508 (5)	C24—C29	1.385 (5)
C9—H9A	0.9600	C24—C23	1.450 (5)
C9—H9B	0.9600	C25—C26	1.379 (6)
C9—H9C	0.9600	C25—H25	0.9300
C10—O1	1.408 (4)	C26—C27	1.375 (6)
C10—H10A	0.9700	C26—H26	0.9300
C10—H10B	0.9700	C27—C28	1.347 (6)
C11—C12	1.366 (5)	C27—H27	0.9300
C11—C16	1.369 (5)	C28—C29	1.388 (5)
C11—O1	1.376 (4)	C28—H28	0.9300
C12—C13	1.376 (5)	C29—O3	1.337 (4)
C12—H12	0.9300	C23—H23	0.9300
C13—C14	1.379 (4)	O3—H3	0.8200
C13—H13	0.9300

C2—C1—H1A	109.5	C13—C14—N1	119.8 (3)
C2—C1—H1B	109.5	C14—C15—C16	120.5 (3)
H1A—C1—H1B	109.5	C14—C15—H15	119.7
C2—C1—H1C	109.5	C16—C15—H15	119.7
H1A—C1—H1C	109.5	C11—C16—C15	119.6 (3)
H1B—C1—H1C	109.5	C11—C16—H16	120.2
O2—C2—C1	109.2 (3)	C15—C16—H16	120.2
O2—C2—H2A	109.8	N1—C17—C22	121.5 (3)
C1—C2—H2A	109.8	N1—C17—C18	120.5 (3)
O2—C2—H2B	109.8	C22—C17—C18	117.9 (3)
C1—C2—H2B	109.8	C19—C18—C17	120.0 (3)
H2A—C2—H2B	108.3	C19—C18—H18	120.0
O2—C3—C4	124.7 (3)	C17—C18—H18	120.0
O2—C3—C8	115.6 (3)	C18—C19—C20	121.7 (3)
C4—C3—C8	119.8 (3)	C18—C19—H19	119.1
C5—C4—C3	119.6 (3)	C20—C19—H19	119.1
C5—C4—H4	120.2	C21—C20—C19	117.6 (3)
C3—C4—H4	120.2	C21—C20—N2	116.8 (3)
C4—C5—C6	121.3 (3)	C19—C20—N2	125.5 (3)
C4—C5—H5	119.4	C22—C21—C20	121.9 (3)
C6—C5—H5	119.4	C22—C21—H21	119.1
C7—C6—C5	118.3 (3)	C20—C21—H21	119.1
C7—C6—N1	120.1 (3)	C21—C22—C17	120.8 (3)
C5—C6—N1	121.5 (3)	C21—C22—H22	119.6
C8—C7—C6	121.0 (3)	C17—C22—H22	119.6
C8—C7—H7	119.5	C23—N2—C20	122.5 (3)
C6—C7—H7	119.5	C25—C24—C29	117.9 (3)
C7—C8—C3	119.9 (3)	C25—C24—C23	120.1 (3)
C7—C8—H8	120.0	C29—C24—C23	121.9 (3)
C3—C8—H8	120.0	C24—C25—C26	121.4 (4)
C10—C9—H9A	109.5	C24—C25—H25	119.3
C10—C9—H9B	109.5	C26—C25—H25	119.3
H9A—C9—H9B	109.5	C27—C26—C25	119.5 (4)
C10—C9—H9C	109.5	C27—C26—H26	120.3
H9A—C9—H9C	109.5	C25—C26—H26	120.3
H9B—C9—H9C	109.5	C28—C27—C26	120.5 (4)
O1—C10—C9	107.3 (3)	C28—C27—H27	119.7
O1—C10—H10A	110.3	C26—C27—H27	119.7
C9—C10—H10A	110.3	C27—C28—C29	119.8 (4)
O1—C10—H10B	110.3	C27—C28—H28	120.1
C9—C10—H10B	110.3	C29—C28—H28	120.1
H10A—C10—H10B	108.5	O3—C29—C24	120.8 (3)
C12—C11—C16	119.9 (3)	O3—C29—C28	118.3 (3)
C12—C11—O1	115.1 (3)	C24—C29—C28	120.9 (4)
C16—C11—O1	125.0 (3)	C17—N1—C6	123.0 (3)
C11—C12—C13	120.5 (3)	C17—N1—C14	120.2 (3)
C11—C12—H12	119.7	C6—N1—C14	116.5 (2)
C13—C12—H12	119.7	N2—C23—C24	122.9 (3)
C12—C13—C14	120.2 (3)	N2—C23—H23	118.5
C12—C13—H13	119.9	C24—C23—H23	118.5
C14—C13—H13	119.9	C11—O1—C10	118.3 (3)
C15—C14—C13	119.2 (3)	C3—O2—C2	118.0 (3)
C15—C14—N1	121.0 (3)	C29—O3—H3	109.5

O2—C3—C4—C5	179.0 (3)	C29—C24—C25—C26	−0.3 (8)
C8—C3—C4—C5	−1.2 (5)	C23—C24—C25—C26	−178.7 (5)
C3—C4—C5—C6	0.9 (5)	C24—C25—C26—C27	−0.8 (11)
C4—C5—C6—C7	0.0 (5)	C25—C26—C27—C28	1.1 (11)
C4—C5—C6—N1	−176.9 (3)	C26—C27—C28—C29	−0.3 (9)
C5—C6—C7—C8	−0.5 (5)	C25—C24—C29—O3	−178.7 (4)
N1—C6—C7—C8	176.4 (3)	C23—C24—C29—O3	−0.3 (6)
C6—C7—C8—C3	0.2 (5)	C25—C24—C29—C28	1.1 (7)
O2—C3—C8—C7	−179.6 (3)	C23—C24—C29—C28	179.5 (4)
C4—C3—C8—C7	0.7 (5)	C27—C28—C29—O3	178.9 (5)
C16—C11—C12—C13	−1.1 (5)	C27—C28—C29—C24	−0.8 (7)
O1—C11—C12—C13	178.3 (3)	C22—C17—N1—C6	164.1 (3)
C11—C12—C13—C14	1.0 (5)	C18—C17—N1—C6	−19.1 (5)
C12—C13—C14—C15	−0.2 (5)	C22—C17—N1—C14	−9.9 (5)
C12—C13—C14—N1	178.6 (3)	C18—C17—N1—C14	166.8 (3)
C13—C14—C15—C16	−0.6 (5)	C7—C6—N1—C17	121.5 (3)
N1—C14—C15—C16	−179.4 (3)	C5—C6—N1—C17	−61.7 (4)
C12—C11—C16—C15	0.3 (5)	C7—C6—N1—C14	−64.3 (4)
O1—C11—C16—C15	−179.1 (3)	C5—C6—N1—C14	112.6 (4)
C14—C15—C16—C11	0.6 (5)	C15—C14—N1—C17	−79.1 (4)
N1—C17—C18—C19	−175.8 (3)	C13—C14—N1—C17	102.1 (4)
C22—C17—C18—C19	1.1 (5)	C15—C14—N1—C6	106.4 (4)
C17—C18—C19—C20	0.0 (5)	C13—C14—N1—C6	−72.3 (4)
C18—C19—C20—C21	−0.7 (5)	C20—N2—C23—C24	−177.0 (3)
C18—C19—C20—N2	176.7 (3)	C25—C24—C23—N2	178.0 (4)
C19—C20—C21—C22	0.2 (5)	C29—C24—C23—N2	−0.3 (6)
N2—C20—C21—C22	−177.3 (3)	C12—C11—O1—C10	172.5 (3)
C20—C21—C22—C17	0.9 (6)	C16—C11—O1—C10	−8.2 (5)
N1—C17—C22—C21	175.3 (3)	C9—C10—O1—C11	−176.7 (3)
C18—C17—C22—C21	−1.5 (5)	C4—C3—O2—C2	−10.3 (4)
C21—C20—N2—C23	−170.9 (3)	C8—C3—O2—C2	170.0 (3)
C19—C20—N2—C23	11.7 (5)	C1—C2—O2—C3	−172.8 (3)

Hydrogen-bond geometry (Å, º) top

Cg1 Cg2 and Cg3 are the centroids of the C3–C8, C11–C16 and C17–C22 benzene rings, respectively.

D—H···A	D—H	H···A	D···A	D—H···A
O3—H3···N2	0.82	1.87	2.605 (4)	148
C1—H1C···Cg2ⁱ	0.96	2.84	3.760 (4)	162
C4—H4···Cg3ⁱⁱ	0.93	2.82	3.655 (3)	150
C9—H9C···Cg1ⁱⁱⁱ	0.96	2.94	3.872 (4)	164
C28—H28···Cg1^iv	0.93	2.88	3.742 (4)	154

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

Hydrogen-bond geometry (Å, º) top

Cg1 Cg2 and Cg3 are the centroids of the C3–C8, C11–C16 and C17–C22 benzene rings, respectively.

D—H···A	D—H	H···A	D···A	D—H···A
O3—H3···N2	0.82	1.87	2.605 (4)	148
C1—H1C···Cg2ⁱ	0.96	2.8370	3.760 (4)	162
C4—H4···Cg3ⁱⁱ	0.93	2.8182	3.655 (3)	150
C9—H9C···Cg1ⁱⁱⁱ	0.96	2.9417	3.872 (4)	164
C28—H28···Cg1^iv	0.93	2.8839	3.742 (4)	154

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

Acknowledgements

This work was supported by the National Natural Science Foundation of China (51372003, 21271004).

References

Bruker (2001). SADABS. Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
Bruker (2007). SMART and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
Dharmaraj, N., Viswanathamurthi, P. & Natarajan, K. (2001). Transition Met. Chem. 26, 105–109. Web of Science CrossRef CAS Google Scholar
Feng, T.-J. (2014). Acta Cryst. E70, o42. CSD CrossRef IUCr Journals Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar
Tanak, H., Toğurman, F., Kalecik, S., Dege, N. & Yavuz, M. (2013). Acta Cryst. E69, o1085. CSD CrossRef IUCr Journals Google Scholar

This is an open-access article distributed under the terms of the Creative Commons Attribution (CC-BY) Licence, which permits unrestricted use, distribution, and reproduction in any medium, provided the original authors and source are cited.

CRYSTALLOGRAPHIC
COMMUNICATIONS

ISSN: 2056-9890

Volume 70| Part 3| March 2014| Page o313

doi:10.1107/S1600536814003201

Open

access