An ortho­rhom­bic polymorph of N1,N4-diphenyl-3,6-bis­(phenyl­imino)­cyclo­hexa-1,4-diene-1,4-di­amine

Ohno, K.; Fujihara, T.; Nagasawa, A.

doi:10.1107/S1600536814006254

organic compounds

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ISSN: 2056-9890

Volume 70| Part 4| April 2014| Pages o495-o496

doi:10.1107/S1600536814006254

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An orthorhombic polymorph of N¹,N⁴-diphenyl-3,6-bis(phenylimino)cyclohexa-1,4-diene-1,4-diamine

Keiji Ohno,^a Takashi Fujihara ^b ^* and Akira Nagasawa ^a

^aDepartment of Chemistry, Graduate School of Science and Engineering, Saitama University, Shimo-Okubo 255, Sakura-ku, Saitama 338-8570, Japan, and ^bComprehensive Analysis Center for Science, Saitama University, Shimo-Okubo 255, Sakura-ku, Saitama 338-8570, Japan
^*Correspondence e-mail: fuji@chem.saitama-u.ac.jp

(Received 5 March 2014; accepted 20 March 2014; online 29 March 2014)

A new orthorhombic polymorph of the title compound, C₃₀H₂₄N₄, with a density of 1.315 Mg m⁻³, has been obtained. The molecule is centrosymmetric with the centroid of the cyclohexa-1,4-diene ring located on an inversion center. The two unique benzene rings are almost perpendicular to each other [dihedral angle = 86.70 (6)°] and are oriented at dihedral angles of 30.79 (5) and 68.07 (5)° with respect to the central cyclohexadiene ring. In the crystal, π–π stacking is observed between the central cyclohexa-1,4-diene-1,4-diamine unit and a phenyl ring of a neighboring molecule [centroid–centroid distance = 3.7043 (7) Å]. The crystal structure of the triclinic polymorph [Ohno et al. (2014 ). Acta Cryst. E70, o303–o304] showed chains running along the b-axis direction through weak C—H⋯π interactions.

CCDC reference: 992862

Related literature

For general background to the title compound, see: Kimish (1875 ). For the triclinic polymorph of the title compound, see: Ohno et al. (2014). For related structures, see: Siri & Braunstein (2000 ); Khramov et al. (2006 ); Boydston et al. (2006 ); Huang et al. (2008 ); Su et al. (2012 ). A calculation using Gaussian98 indicates that the triclinic form of the title compound is more stable, see: Frisch et al. (2001 ).

Experimental

Crystal data

C₃₀H₂₄N₄
M_r = 440.53
Orthorhombic, P b c a
a = 9.1927 (5) Å
b = 12.4711 (7) Å
c = 18.9806 (11) Å
V = 2176.0 (2) Å³
Z = 4
Mo Kα radiation
μ = 0.08 mm⁻¹
T = 173 K
0.35 × 0.30 × 0.10 mm

Data collection

Bruker SMART APEX CCD area-detector diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2001 ) T_min = 0.97, T_max = 0.99
14830 measured reflections
2591 independent reflections
2193 reflections with I > 2σ(I)
R_int = 0.116

Refinement

R[F² > 2σ(F²)] = 0.046
wR(F²) = 0.133
S = 1.09
2591 reflections
158 parameters
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.31 e Å⁻³
Δρ_min = −0.24 e Å⁻³

Data collection: SMART (Bruker, 2007 ); cell refinement: SAINT (Bruker, 2007); data reduction: SAINT; program(s) used to solve structure: SHELXTL (Sheldrick, 2008 ); program(s) used to refine structure: SHELXTL; molecular graphics: ORTEP-3 for Windows (Farrugia, 2012 ); software used to prepare material for publication: SHELXTL.

Supporting information

CCDC reference: 992862

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536814006254/xu5776sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536814006254/xu5776Isup2.hkl

Supporting information file. DOI: 10.1107/S1600536814006254/xu5776Isup3.cml

checkCIF report

Comment top

N¹,N⁴-Diphenyl-3,6-bis(phenylimino)cyclohexa-1,4-diene-1,4-diamine (I) was synthesized as early as in 1875 (Kimish, 1875) and called azophenine. Recently derivatives of I were prepared and these molecular structures were reported (Siri & Braunstein, 2000; Khramov et al., 2006; Boydston et al., 2006; Huang et al., 2008; Su et al., 2012). Previously, we reported the molecular structure of I in triclinic P-1 space group, which is obtained from an oxidation reaction of aniline in the presence of [V^IV(O)(η²-ox)(H₂O)₃] (ox^2- = oxalate) in a mixture of EtOH and H₂O (Ohno et al., 2014).

We obtained the crystals of I in orthorhombic Pbca space group from a reaction with aniline and [V^IV(O)(η²-ox)(H₂O)₃] and will report here its molecular and crystal structures. This crystal is a porymorph of the previously reported triclinic structure, which showed one-dimensional chains running along the b-axis direction through weak C—H···π interactions in the crystal.

The crystals contain only I. The main structural difference between the polymorphs of I lies in the orientation of phenyl rings (Figure 2). The neighboring phenyl rings in orthorhombic polymorph of I locate near perpendicular with each other, where the dihedral angle between C(4)—C(5)—C(6)—C(7)—C(8)—C(9) and C(10 A)—C(11 A)—C(12 A)—C(13 A)—C(14 A)—C(15 A) phenyl rings is 86.71°. On the other hand, the dihedral angles between neighboring phenyl rings in triclinic polymorph of I are 29.46 and 19.69° for between C(7)—C(8)—C(9)—C(10)—C(11)—C(12) and C(25)—C(26)—C(27)—C(28)—C(29)—C(30) phenyl rings and C(13)—C(14)—C(15)—C(16)— C(17)—C(18) and C(19)—C(20)—C(21)—C(22)—C(23)—C(24) ones, respectively.

Packing structure of the orthorhombic polymorph of I represented two-dimensional sheets through intermolecular π–π interaction, where the distances between the phenyl ring C(10)—C(11)—C(12)—C(13)—C(14)—C(15) and the central six-membered ring of adjacent molecule C(1)—C(2)—C(3)—C(1 A)—C(2 A)—C(3 A) is about 3.54 Å (the symmetry code: -x + 0.5, y - 0.5, z) and the dihedral angle between them is 10.70 (8)° (Figure 3).

Calculations using Gaussian98 (Frisch et al., 2001) with a B3LYP/6–31 G(d) set of parameters for polymorphs indicate that the triclinic form is more stable than the monoclinic form by approximately 10 kJ mol^-1.

Related literature top

For general background to the title compound, see: Kimish (1875). For the triclinic polymorph of the title compound, see: Ohno et al. (2014). For related structures, see: Siri & Braunstein (2000); Khramov et al. (2006); Boydston et al. (2006); Huang et al. (2008); Su et al. (2012). A calculation using Gaussian98 indicates that the triclinic form of the title compound is more stable, see: Frisch et al. (2001).

Experimental top

The V^IV complex [V^IV(O)(η²-ox)(H₂O)₃] was purchased as "VO(ox)^.nH₂O" from Wako Chemicals, and used without further purification. A solution of aniline (27.9 g, 300 mmol) in EtOH (50 cm³) was added to a solution of VO(ox)^.nH₂O (1.13 g, 3.00 mmol) in a mixture of EtOH (50 cm³) and H₂O (100 cm³). The reaction mixture was set aside for 2 weeks at room temperature in air. The precipitated crystals of I were filtered off, washed with H₂O and EtOH, successively, and dried. Yield 1.34 g. (5.1%). ¹H NMR / CDCl₃: δ 8.22 (s, 2H, NH), 7.41–6.88 (m, 20H, PhH), 6.21 (s, 2H, CH). MALDI TOF MS: 441 (M+1). UV-vis / CH₂Cl₂, λ/nm (ε/M^-1cm^-1): 290 (46000), 379 (30000).

Computing details top

Data collection: SMART (Bruker, 2007); cell refinement: SAINT (Bruker, 2007); data reduction: SAINT (Bruker, 2007); program(s) used to solve structure: SHELXTL (Sheldrick, 2008); program(s) used to refine structure: SHELXTL (Sheldrick, 2008); molecular graphics: ORTEP-3 for Windows (Farrugia, 2012); software used to prepare material for publication: SHELXTL (Sheldrick, 2008).

Figures top

	Fig. 1. The molecular structure in the orthorhombic polymorph of I, with displacement ellipsoids drawn at the 50% probability level.
	Fig. 2. A superposition of the molecular structures of the orthorhombic polymorph of I (colour: black) and the triclinic one (colour: orange).
	Fig. 3. The packing structure through intermolecular π–π interaction in the orthorhombic polymorph of I.

N¹,N⁴-Diphenyl-3,6-bis(phenylimino)cyclohexa-1,4-diene-1,4-diamine top

Crystal data top

C₃₀H₂₄N₄	F(000) = 928
M_r = 440.53	D_x = 1.345 Mg m⁻³
Orthorhombic, Pbca	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ac 2ab	Cell parameters from 6200 reflections
a = 9.1927 (5) Å	θ = 3.0–27.8°
b = 12.4711 (7) Å	µ = 0.08 mm⁻¹
c = 18.9806 (11) Å	T = 173 K
V = 2176.0 (2) Å³	Plate, orange
Z = 4	0.35 × 0.30 × 0.10 mm

Data collection top

Bruker SMART APEX CCD area-detector diffractometer	2591 independent reflections
Radiation source: fine-focus sealed tube	2193 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.116
Detector resolution: 8.366 pixels mm^-1	θ_max = 27.9°, θ_min = 2.2°
ϕ and ω scans	h = −12→11
Absorption correction: multi-scan (SADABS; Bruker, 2001)	k = −16→15
T_min = 0.97, T_max = 0.99	l = −16→24
14830 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)] = 0.046	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.133	H atoms treated by a mixture of independent and constrained refinement
S = 1.09	w = 1/[σ²(F_o²) + (0.073P)² + 0.1882P] where P = (F_o² + 2F_c²)/3
2591 reflections	(Δ/σ)_max < 0.001
158 parameters	Δρ_max = 0.31 e Å⁻³
0 restraints	Δρ_min = −0.24 e Å⁻³

Crystal data top

C₃₀H₂₄N₄	V = 2176.0 (2) Å³
M_r = 440.53	Z = 4
Orthorhombic, Pbca	Mo Kα radiation
a = 9.1927 (5) Å	µ = 0.08 mm⁻¹
b = 12.4711 (7) Å	T = 173 K
c = 18.9806 (11) Å	0.35 × 0.30 × 0.10 mm

Data collection top

Bruker SMART APEX CCD area-detector diffractometer	2591 independent reflections
Absorption correction: multi-scan (SADABS; Bruker, 2001)	2193 reflections with I > 2σ(I)
T_min = 0.97, T_max = 0.99	R_int = 0.116
14830 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.046	0 restraints
wR(F²) = 0.133	H atoms treated by a mixture of independent and constrained refinement
S = 1.09	Δρ_max = 0.31 e Å⁻³
2591 reflections	Δρ_min = −0.24 e Å⁻³
158 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.

Least-squares planes (x,y,z in crystal coordinates) and deviations from them (* indicates atom used to define plane)

- 4.5932 (0.0050) x + 6.9089 (0.0064) y + 12.6394 (0.0086) z = 6.3197 (0.0043)

* 0.0005 (0.0006) C1 * -0.0005 (0.0006) C2 * 0.0005 (0.0006) C3 * -0.0005 (0.0006) C1_$1 * 0.0005 (0.0006) C2_$1 * -0.0005 (0.0006) C3_$1

Rms deviation of fitted atoms = 0.0005

- 5.6034 (0.0038) x + 5.0416 (0.0058) y + 12.9434 (0.0070) z = 2.9266 (0.0041)

Angle to previous plane (with approximate e.s.d.) = 10.70 (0.08)

* 0.0006 (0.0008) C10_$2 * -0.0066 (0.0008) C11_$2 * 0.0067 (0.0009) C12_$2 * -0.0008 (0.0009) C13_$2 * -0.0053 (0.0009) C14_$2 * 0.0053 (0.0008) C15_$2

Rms deviation of fitted atoms = 0.0049

- 4.5932 (0.0050) x + 6.9089 (0.0064) y + 12.6394 (0.0086) z = 6.3197 (0.0043)

Angle to previous plane (with approximate e.s.d.) = 10.70 (0.08)

* 0.0005 (0.0006) C1 * -0.0005 (0.0006) C2 * 0.0005 (0.0006) C3 * -0.0005 (0.0006) C1_$1 * 0.0005 (0.0006) C2_$1 * -0.0005 (0.0006) C3_$1 - 3.7228 (0.0017) C10_$2 - 3.4796 (0.0019) C11_$2 - 3.2849 (0.0018) C12_$2

Rms deviation of fitted atoms = 0.0005

- 4.5932 (0.0050) x + 6.9089 (0.0064) y + 12.6394 (0.0086) z = 6.3197 (0.0043)

Angle to previous plane (with approximate e.s.d.) = 0.00 (0.10)

* 0.0005 (0.0006) C1 * -0.0005 (0.0006) C2 * 0.0005 (0.0006) C3 * -0.0005 (0.0006) C1_$1 * 0.0005 (0.0006) C2_$1 * -0.0005 (0.0006) C3_$1 - 3.3572 (0.0015) C13_$2 - 3.6100 (0.0013) C14_$2 - 3.7830 (0.0014) C15_$2

Rms deviation of fitted atoms = 0.0005

- 7.4963 (0.0028) x + 1.7481 (0.0065) y + 10.6592 (0.0082) z = 4.5261 (0.0067)

Angle to previous plane (with approximate e.s.d.) = 30.79 (0.06)

* 0.0118 (0.0008) C4 * -0.0134 (0.0008) C5 * 0.0021 (0.0009) C6 * 0.0111 (0.0009) C7 * -0.0128 (0.0009) C8 * 0.0013 (0.0009) C9

Rms deviation of fitted atoms = 0.0101

5.6034 (0.0038) x + 5.0416 (0.0058) y + 12.9434 (0.0071) z = 8.2491 (0.0021)

Angle to previous plane (with approximate e.s.d.) = 86.71 (0.03)

* 0.0006 (0.0008) C10 * -0.0066 (0.0008) C11 * 0.0067 (0.0009) C12 * -0.0008 (0.0009) C13 * -0.0053 (0.0009) C14 * 0.0053 (0.0008) C15

Rms deviation of fitted atoms = 0.004

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

	x	y	z	U_iso*/U_eq
C1	0.12006 (12)	−0.00788 (8)	0.54798 (6)	0.0209 (3)
C2	0.10916 (12)	0.08101 (8)	0.49535 (6)	0.0206 (3)
C3	−0.01449 (12)	0.08355 (9)	0.44911 (6)	0.0215 (3)
H3	−0.0224	0.1398	0.4156	0.026*
C4	0.29282 (12)	−0.06850 (9)	0.64289 (6)	0.0219 (3)
C5	0.27035 (13)	−0.17924 (10)	0.64288 (6)	0.0256 (3)
H5	0.2148	−0.2119	0.6065	0.031*
C6	0.32978 (14)	−0.24128 (10)	0.69630 (7)	0.0301 (3)
H6	0.3123	−0.3164	0.6968	0.036*
C7	0.41411 (15)	−0.19588 (10)	0.74902 (6)	0.0321 (3)
H7	0.4531	−0.2392	0.7856	0.039*
C8	0.44080 (15)	−0.08662 (10)	0.74762 (6)	0.0314 (3)
H8	0.5013	−0.0551	0.7825	0.038*
C9	0.37968 (13)	−0.02321 (9)	0.69556 (6)	0.0264 (3)
H9	0.3969	0.0519	0.6956	0.032*
C10	0.21200 (12)	0.24083 (9)	0.45179 (6)	0.0223 (3)
C11	0.11033 (13)	0.32190 (10)	0.46367 (6)	0.0262 (3)
H11	0.0366	0.3124	0.4982	0.031*
C12	0.11658 (14)	0.41614 (9)	0.42529 (7)	0.0280 (3)
H12	0.0483	0.4717	0.4343	0.034*
C13	0.22200 (14)	0.43007 (10)	0.37364 (7)	0.0288 (3)
H13	0.2254	0.4945	0.3469	0.035*
C14	0.32205 (14)	0.34921 (10)	0.36147 (7)	0.0291 (3)
H14	0.3940	0.3582	0.3260	0.035*
C15	0.31853 (13)	0.25534 (9)	0.40038 (6)	0.0254 (3)
H15	0.3887	0.2008	0.3921	0.031*
H1	0.2849 (18)	0.0610 (13)	0.5831 (8)	0.030 (4)*
N1	0.23876 (11)	0.00087 (8)	0.59090 (5)	0.0248 (2)
N2	0.21592 (10)	0.14848 (8)	0.49516 (5)	0.0236 (2)

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
C1	0.0178 (5)	0.0226 (5)	0.0223 (5)	0.0024 (4)	−0.0001 (4)	−0.0009 (4)
C2	0.0181 (5)	0.0207 (5)	0.0231 (5)	0.0007 (4)	0.0008 (4)	−0.0010 (4)
C3	0.0197 (5)	0.0220 (5)	0.0229 (5)	0.0005 (4)	−0.0010 (4)	0.0020 (4)
C4	0.0160 (5)	0.0264 (6)	0.0234 (5)	0.0013 (4)	0.0005 (4)	0.0022 (4)
C5	0.0198 (6)	0.0265 (6)	0.0305 (6)	−0.0003 (4)	−0.0015 (4)	−0.0008 (4)
C6	0.0243 (6)	0.0266 (6)	0.0393 (7)	0.0012 (5)	0.0003 (5)	0.0055 (5)
C7	0.0288 (7)	0.0374 (7)	0.0302 (6)	0.0062 (5)	−0.0025 (5)	0.0084 (5)
C8	0.0267 (7)	0.0395 (7)	0.0279 (6)	0.0026 (5)	−0.0061 (5)	−0.0014 (5)
C9	0.0233 (6)	0.0267 (6)	0.0291 (6)	0.0007 (4)	−0.0032 (4)	−0.0007 (4)
C10	0.0183 (5)	0.0222 (5)	0.0264 (6)	−0.0041 (4)	−0.0045 (4)	0.0007 (4)
C11	0.0201 (6)	0.0287 (6)	0.0297 (6)	−0.0013 (4)	0.0015 (4)	0.0006 (4)
C12	0.0225 (6)	0.0250 (6)	0.0364 (7)	0.0025 (4)	−0.0017 (5)	−0.0001 (5)
C13	0.0282 (6)	0.0251 (6)	0.0330 (6)	−0.0032 (5)	−0.0028 (5)	0.0064 (5)
C14	0.0244 (6)	0.0326 (6)	0.0301 (6)	−0.0035 (5)	0.0032 (5)	0.0038 (5)
C15	0.0202 (6)	0.0264 (6)	0.0296 (6)	0.0006 (4)	−0.0014 (4)	−0.0002 (4)
N1	0.0217 (5)	0.0237 (5)	0.0290 (5)	−0.0051 (4)	−0.0059 (4)	0.0044 (4)
N2	0.0194 (5)	0.0227 (5)	0.0286 (5)	−0.0017 (4)	−0.0019 (4)	0.0021 (4)

Geometric parameters (Å, º) top

C1—C3ⁱ	1.3547 (16)	C8—C9	1.3847 (17)
C1—N1	1.3662 (15)	C8—H8	0.9500
C1—C2	1.4957 (15)	C9—H9	0.9500
C2—N2	1.2927 (14)	C10—C15	1.3942 (17)
C2—C3	1.4365 (15)	C10—C11	1.3952 (17)
C3—C1ⁱ	1.3547 (16)	C10—N2	1.4160 (14)
C3—H3	0.9500	C11—C12	1.3840 (17)
C4—C5	1.3964 (16)	C11—H11	0.9500
C4—C9	1.3985 (16)	C12—C13	1.3893 (18)
C4—N1	1.4032 (15)	C12—H12	0.9500
C5—C6	1.3874 (17)	C13—C14	1.3842 (18)
C5—H5	0.9500	C13—H13	0.9500
C6—C7	1.3866 (19)	C14—C15	1.3846 (16)
C6—H6	0.9500	C14—H14	0.9500
C7—C8	1.3848 (19)	C15—H15	0.9500
C7—H7	0.9500	N1—H1	0.874 (17)

C3ⁱ—C1—N1	127.12 (10)	C8—C9—H9	119.6
C3ⁱ—C1—C2	119.71 (10)	C4—C9—H9	119.6
N1—C1—C2	113.12 (10)	C15—C10—C11	119.31 (10)
N2—C2—C3	125.78 (10)	C15—C10—N2	119.63 (10)
N2—C2—C1	115.69 (10)	C11—C10—N2	120.83 (10)
C3—C2—C1	118.51 (10)	C12—C11—C10	120.17 (11)
C1ⁱ—C3—C2	121.78 (10)	C12—C11—H11	119.9
C1ⁱ—C3—H3	119.1	C10—C11—H11	119.9
C2—C3—H3	119.1	C11—C12—C13	120.44 (11)
C5—C4—C9	118.94 (10)	C11—C12—H12	119.8
C5—C4—N1	123.87 (10)	C13—C12—H12	119.8
C9—C4—N1	117.12 (10)	C14—C13—C12	119.34 (11)
C6—C5—C4	119.55 (11)	C14—C13—H13	120.3
C6—C5—H5	120.2	C12—C13—H13	120.3
C4—C5—H5	120.2	C13—C14—C15	120.76 (11)
C7—C6—C5	121.32 (11)	C13—C14—H14	119.6
C7—C6—H6	119.3	C15—C14—H14	119.6
C5—C6—H6	119.3	C14—C15—C10	119.96 (11)
C8—C7—C6	119.14 (11)	C14—C15—H15	120.0
C8—C7—H7	120.4	C10—C15—H15	120.0
C6—C7—H7	120.4	C1—N1—C4	130.77 (10)
C9—C8—C7	120.25 (12)	C1—N1—H1	110.7 (10)
C9—C8—H8	119.9	C4—N1—H1	118.5 (10)
C7—C8—H8	119.9	C2—N2—C10	120.77 (10)
C8—C9—C4	120.74 (11)

C3ⁱ—C1—C2—N2	−178.63 (10)	N2—C10—C11—C12	173.81 (11)
N1—C1—C2—N2	3.91 (14)	C10—C11—C12—C13	1.35 (18)
C3ⁱ—C1—C2—C3	0.14 (17)	C11—C12—C13—C14	−0.79 (19)
N1—C1—C2—C3	−177.31 (10)	C12—C13—C14—C15	−0.37 (19)
N2—C2—C3—C1ⁱ	178.50 (11)	C13—C14—C15—C10	0.95 (18)
C1—C2—C3—C1ⁱ	−0.14 (17)	C11—C10—C15—C14	−0.38 (17)
C9—C4—C5—C6	2.39 (17)	N2—C10—C15—C14	−175.02 (10)
N1—C4—C5—C6	179.27 (11)	C3ⁱ—C1—N1—C4	7.7 (2)
C4—C5—C6—C7	−1.51 (18)	C2—C1—N1—C4	−175.09 (11)
C5—C6—C7—C8	−0.8 (2)	C5—C4—N1—C1	26.84 (19)
C6—C7—C8—C9	2.2 (2)	C9—C4—N1—C1	−156.22 (12)
C7—C8—C9—C4	−1.33 (19)	C3—C2—N2—C10	6.60 (17)
C5—C4—C9—C8	−1.00 (18)	C1—C2—N2—C10	−174.73 (9)
N1—C4—C9—C8	−178.09 (11)	C15—C10—N2—C2	−119.41 (12)
C15—C10—C11—C12	−0.76 (17)	C11—C10—N2—C2	66.04 (14)

Symmetry code: (i) −x, −y, −z+1.

Experimental details

Crystal data
Chemical formula	C₃₀H₂₄N₄
M_r	440.53
Crystal system, space group	Orthorhombic, Pbca
Temperature (K)	173
a, b, c (Å)	9.1927 (5), 12.4711 (7), 18.9806 (11)
V (Å³)	2176.0 (2)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.08
Crystal size (mm)	0.35 × 0.30 × 0.10

Data collection
Diffractometer	Bruker SMART APEX CCD area-detector diffractometer
Absorption correction	Multi-scan (SADABS; Bruker, 2001)
T_min, T_max	0.97, 0.99
No. of measured, independent and observed [I > 2σ(I)] reflections	14830, 2591, 2193
R_int	0.116
(sin θ/λ)_max (Å⁻¹)	0.658

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.046, 0.133, 1.09
No. of reflections	2591
No. of parameters	158
H-atom treatment	H atoms treated by a mixture of independent and constrained refinement
Δρ_max, Δρ_min (e Å⁻³)	0.31, −0.24

Computer programs: SMART (Bruker, 2007), SAINT (Bruker, 2007), SHELXTL (Sheldrick, 2008), ORTEP-3 for Windows (Farrugia, 2012).

Acknowledgements

This work was supported by the programs of the Grants-in-Aid for Scientific Research (to TF, No. 23510115) from the Japan Society for the Promotion of Science.

References

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Volume 70| Part 4| April 2014| Pages o495-o496

doi:10.1107/S1600536814006254

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