3,5,3′,5′-Tetra­methyl-N,N′-bis­(salicyl­idene)biphenyl-4,4′-diamine

Xu, L.; Kim, Y.; Kim, S.-J.

doi:10.1107/S1600536805029260

3,5,3′,5′-Tetramethyl-N,N′-bis(salicylidene)biphenyl-4,4′-diamine

In the molecule of the title Schiff base compound, C₃₀H₂₈N₂O₂, the dihedral angles between the phenol rings and the adjacent dimethylbenzene rings [60.14 (11) and 77.57 (11)°] are distinctly larger than that formed by the dimethylbenzene rings [39.65 (11)°], possibly as a result of the steric hindrance of the methyl groups and the presence of intramolecular O—H

N hydrogen bonds.

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Supporting information

	Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536805029260/rz6110sup1.cif Contains datablocks global, I
	Structure factor file (CIF format) https://doi.org/10.1107/S1600536805029260/rz6110Isup2.hkl Contains datablock I

CCDC reference: 287696

checkCIF report

Key indicators

Single-crystal X-ray study
T = 273 K
Mean (C-C) = 0.005 Å
R factor = 0.064
wR factor = 0.173
Data-to-parameter ratio = 13.7

checkCIF/PLATON results

No syntax errors found



Alert level C
RINTA01_ALERT_3_C  The value of Rint is greater than 0.10
            Rint given   0.101
PLAT020_ALERT_3_C The value of Rint is greater than 0.10 .........       0.10
PLAT026_ALERT_3_C Ratio Observed / Unique Reflections too Low ....         44 Perc.
PLAT250_ALERT_2_C Large U3/U1 Ratio for Average U(i,j) Tensor ....       2.66
PLAT340_ALERT_3_C Low Bond Precision on C-C bonds (x 1000) Ang ...          5

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

   0 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
   4 ALERT type 3 Indicator that the structure quality may be low
   0 ALERT type 4 Improvement, methodology, query or suggestion

Comment top

Multidentate Schiff base ligands and their metal complexes have been studied for many years (Daier et al., 2004; Munro & Camp, 2003; Weber, 1967). These complexes play an important role in the development of coordination chemistry related to magnetism, catalysis and molecular architectures. As a continuation of our previous work (Xu et al., 2001), we report here the structure of the title compound, (I).

Compound (I) crystallizes in the space group P2₁/c. Selected bond distances and angles are listed in Table 1. The molecule contains four aromatic rings (Fig. 1). The dihedral angles formed by the C1–C6 and C25–C30 phenol rings with the adjacent C8–C13 and C16–C21 dimethylbenzene rings are 60.14 (11) and 77.57 (11)°, respectively. These angles are remarkably larger than that formed by the dimethylbenzene rings [39.65 (11)°], possibly due to the concomitant effects of the steric hindrance of the methyl groups and the presence of two intramolecular O—H···N hydrogen-bond interactions (Table 2). There are neither π–π stacking nor weak intermolecular hydrogen-bond interactions, and the crystal packing (Fig. 2) is controlled by van der Waals forces.

Experimental top

The title compound was synthesized by the condensation of salicylaldehyde and 3,3',5,5'-tetramethylbenzidine. A mixture of 3,3',5,5'-tetramethylbenzidine (0.59 mmol) in MeOH (10 ml) and salicylaldehyde (1 mmol) in MeOH (10 ml) was refluxed for 3 h under an N₂ atmosphere and allowed to stand at room temperature overnight. The yellow solid product was isolated by filtration and washed with MeOH (yield: 61%). Pale-yellow single crystals suitable for X-ray diffraction were obtained by slow evaporation of a methanol solution (m.p. 480 K). ¹H NMR (300 MHz, CDCl₃): 2.29 (s, 12H, CH₃), 6.95–7.10 (m, 4H, Ph), 7.22–7.75 (m, 8H, Ph), 8.41 (s, 2H,CH).

Computing details top

Data collection: SMART (Bruker, 1997); cell refinement: SAINT (Bruker, 1997); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: SHELXTL (Bruker, 1998); software used to prepare material for publication: SHELXTL.

Figures top

	Fig. 1. The structure of (I), showing 50% probability displacement ellipsoids and the atom-numbering scheme. The O—H···N hydrogen-bond interactions are indicated by dashed lines.
	Fig. 2. The crystal packing of the title compound, viewed down the [100] direction. H atoms have been omitted for clarity. Displacement ellipsoids are drawn at the 50% probability level.

3,5,3',5'-Tetramethyl-N,N'-bis(salicylidene)biphenyl-4,4'-diamine top

Crystal data top

C₃₀H₂₈N₂O₂	F(000) = 952
M_r = 448.54	D_x = 1.223 Mg m⁻³
Monoclinic, P2₁/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 661 reflections
a = 10.693 (5) Å	θ = 2.5–18.1°
b = 12.896 (6) Å	µ = 0.08 mm⁻¹
c = 17.673 (8) Å	T = 273 K
β = 90.871 (9)°	Block, pale yellow
V = 2436.7 (19) Å³	0.12 × 0.09 × 0.06 mm
Z = 4

Data collection top

Bruker SMART CCD area-detector diffractometer	1897 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	R_int = 0.102
Graphite monochromator	θ_max = 25.0°, θ_min = 1.9°
ϕ and ω scans	h = −12→12
12159 measured reflections	k = −8→15
4289 independent reflections	l = −20→21

Refinement top

Refinement on F²	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F² > 2σ(F²)] = 0.064	H-atom parameters constrained
wR(F²) = 0.173	w = 1/[σ²(F_o²) + (0.0555P)²] where P = (F_o² + 2F_c²)/3
S = 0.93	(Δ/σ)_max = 0.001
4289 reflections	Δρ_max = 0.23 e Å⁻³
314 parameters	Δρ_min = −0.21 e Å⁻³
0 restraints	Extinction correction: SHELXL97, Fc^*=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.0088 (13)

Crystal data top

C₃₀H₂₈N₂O₂	V = 2436.7 (19) Å³
M_r = 448.54	Z = 4
Monoclinic, P2₁/c	Mo Kα radiation
a = 10.693 (5) Å	µ = 0.08 mm⁻¹
b = 12.896 (6) Å	T = 273 K
c = 17.673 (8) Å	0.12 × 0.09 × 0.06 mm
β = 90.871 (9)°

Data collection top

Bruker SMART CCD area-detector diffractometer	1897 reflections with I > 2σ(I)
12159 measured reflections	R_int = 0.102
4289 independent reflections

Refinement top

R[F² > 2σ(F²)] = 0.064	0 restraints
wR(F²) = 0.173	H-atom parameters constrained
S = 0.93	Δρ_max = 0.23 e Å⁻³
4289 reflections	Δρ_min = −0.21 e Å⁻³
314 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	0.6992 (3)	0.2741 (3)	0.34697 (19)	0.0467 (10)
C2	0.7802 (4)	0.2645 (3)	0.4090 (2)	0.0601 (12)
H2A	0.8663	0.2672	0.4022	0.072*
C3	0.7335 (4)	0.2513 (3)	0.4793 (2)	0.0530 (11)
H3	0.7885	0.2455	0.5204	0.064*
C4	0.6079 (4)	0.2463 (3)	0.4912 (2)	0.0529 (11)
H4	0.5774	0.2362	0.5397	0.064*
C5	0.5265 (3)	0.2566 (3)	0.42996 (19)	0.0479 (10)
H5	0.4407	0.2540	0.4376	0.058*
C6	0.5711 (3)	0.2706 (3)	0.35743 (18)	0.0368 (9)
C7	0.4819 (3)	0.2835 (3)	0.29432 (18)	0.0413 (9)
H7	0.3967	0.2826	0.3041	0.050*
C8	0.4275 (3)	0.3144 (3)	0.16633 (17)	0.0363 (9)
C9	0.3404 (3)	0.2387 (3)	0.14418 (17)	0.0357 (9)
C10	0.2643 (3)	0.2604 (3)	0.08110 (18)	0.0367 (9)
H10	0.2068	0.2106	0.0651	0.044*
C11	0.2709 (3)	0.3534 (3)	0.04119 (17)	0.0350 (8)
C12	0.3586 (3)	0.4267 (3)	0.06545 (17)	0.0377 (9)
H12	0.3636	0.4897	0.0400	0.045*
C13	0.4395 (3)	0.4080 (3)	0.12718 (17)	0.0369 (9)
C14	0.5418 (3)	0.4847 (3)	0.14726 (19)	0.0520 (11)
H14A	0.5358	0.5036	0.1996	0.078*
H14B	0.5326	0.5455	0.1164	0.078*
H14C	0.6219	0.4537	0.1385	0.078*
C15	0.3310 (3)	0.1349 (3)	0.18256 (18)	0.0481 (10)
H15A	0.4134	0.1081	0.1923	0.072*
H15B	0.2856	0.0877	0.1503	0.072*
H15C	0.2879	0.1426	0.2295	0.072*
C16	0.1930 (3)	0.3732 (3)	−0.02820 (17)	0.0324 (8)
C17	0.1702 (3)	0.2936 (3)	−0.08082 (17)	0.0359 (9)
H17	0.1985	0.2270	−0.0700	0.043*
C18	0.1064 (3)	0.3116 (3)	−0.14875 (17)	0.0336 (8)
C19	0.0625 (3)	0.4115 (3)	−0.16283 (17)	0.0343 (8)
C20	0.0810 (3)	0.4927 (3)	−0.11198 (17)	0.0342 (8)
C21	0.1468 (3)	0.4710 (3)	−0.04497 (17)	0.0349 (8)
H21	0.1601	0.5242	−0.0103	0.042*
C22	0.0360 (3)	0.6009 (3)	−0.12849 (18)	0.0456 (10)
H22A	0.0871	0.6314	−0.1667	0.068*
H22B	0.0415	0.6418	−0.0832	0.068*
H22C	−0.0493	0.5985	−0.1461	0.068*
C23	0.0860 (3)	0.2257 (3)	−0.20559 (18)	0.0448 (10)
H23A	0.1374	0.1673	−0.1921	0.067*
H23B	0.1079	0.2498	−0.2550	0.067*
H23C	−0.0004	0.2053	−0.2058	0.067*
C24	−0.1144 (3)	0.4369 (3)	−0.24260 (17)	0.0379 (9)
H24	−0.1630	0.4283	−0.1999	0.045*
C25	−0.1761 (3)	0.4566 (2)	−0.31533 (18)	0.0360 (9)
C26	−0.3064 (3)	0.4673 (3)	−0.3194 (2)	0.0525 (11)
H26	−0.3532	0.4586	−0.2760	0.063*
C27	−0.3664 (4)	0.4907 (3)	−0.3870 (2)	0.0555 (11)
H27	−0.4528	0.4984	−0.3889	0.067*
C28	−0.2977 (4)	0.5024 (3)	−0.4513 (2)	0.0505 (10)
H28	−0.3384	0.5179	−0.4968	0.061*
C29	−0.1692 (3)	0.4914 (3)	−0.44978 (19)	0.0506 (10)
H29	−0.1236	0.4990	−0.4938	0.061*
C30	−0.1091 (3)	0.4688 (3)	−0.38156 (18)	0.0404 (9)
N1	0.5174 (2)	0.2961 (2)	0.22647 (15)	0.0396 (8)
N2	0.0043 (3)	0.4310 (2)	−0.23580 (14)	0.0401 (8)
O1	0.7480 (2)	0.2884 (3)	0.27771 (13)	0.0749 (10)
H1	0.6914	0.2987	0.2468	0.112*
O2	0.0173 (2)	0.4599 (3)	−0.38157 (13)	0.0702 (9)
H2	0.0437	0.4559	−0.3379	0.105*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
C1	0.038 (2)	0.073 (3)	0.029 (2)	0.012 (2)	−0.0092 (17)	0.0004 (19)
C2	0.039 (2)	0.103 (3)	0.038 (2)	0.013 (2)	−0.0145 (19)	−0.005 (2)
C3	0.062 (3)	0.061 (3)	0.035 (2)	0.008 (2)	−0.022 (2)	0.0015 (19)
C4	0.063 (3)	0.068 (3)	0.027 (2)	−0.011 (2)	−0.0114 (19)	0.0109 (19)
C5	0.044 (2)	0.067 (3)	0.032 (2)	−0.012 (2)	−0.0076 (17)	0.0057 (19)
C6	0.037 (2)	0.044 (2)	0.0293 (19)	0.0013 (17)	−0.0106 (16)	0.0023 (16)
C7	0.034 (2)	0.056 (3)	0.033 (2)	−0.0008 (18)	−0.0090 (17)	0.0024 (18)
C8	0.0302 (19)	0.056 (3)	0.0223 (18)	0.0060 (18)	−0.0070 (15)	−0.0008 (18)
C9	0.035 (2)	0.045 (2)	0.0266 (18)	0.0036 (17)	−0.0035 (15)	0.0045 (17)
C10	0.032 (2)	0.044 (2)	0.0336 (19)	−0.0008 (17)	−0.0096 (16)	0.0008 (17)
C11	0.034 (2)	0.044 (2)	0.0264 (19)	0.0037 (18)	−0.0054 (15)	−0.0027 (17)
C12	0.038 (2)	0.047 (2)	0.0273 (19)	0.0017 (18)	−0.0098 (16)	−0.0013 (16)
C13	0.042 (2)	0.046 (2)	0.0226 (18)	0.0001 (18)	−0.0066 (16)	−0.0025 (17)
C14	0.051 (2)	0.064 (3)	0.040 (2)	−0.008 (2)	−0.0148 (19)	−0.0026 (19)
C15	0.042 (2)	0.061 (3)	0.041 (2)	−0.002 (2)	−0.0115 (17)	0.0114 (19)
C16	0.0278 (19)	0.045 (2)	0.0238 (18)	−0.0011 (17)	−0.0064 (15)	0.0003 (17)
C17	0.0344 (19)	0.038 (2)	0.035 (2)	0.0002 (16)	−0.0142 (16)	0.0027 (17)
C18	0.0294 (19)	0.046 (2)	0.0254 (18)	0.0021 (17)	−0.0086 (15)	−0.0052 (17)
C19	0.0292 (19)	0.052 (2)	0.0219 (18)	−0.0019 (17)	−0.0088 (14)	0.0018 (17)
C20	0.034 (2)	0.041 (2)	0.0267 (19)	0.0041 (17)	−0.0072 (15)	0.0012 (17)
C21	0.040 (2)	0.039 (2)	0.0255 (18)	−0.0031 (17)	−0.0111 (15)	0.0021 (16)
C22	0.049 (2)	0.049 (3)	0.038 (2)	0.0049 (19)	−0.0167 (18)	0.0009 (18)
C23	0.047 (2)	0.050 (2)	0.036 (2)	0.0036 (19)	−0.0150 (17)	−0.0064 (18)
C24	0.040 (2)	0.047 (2)	0.0267 (19)	−0.0023 (18)	−0.0100 (16)	0.0015 (17)
C25	0.038 (2)	0.039 (2)	0.031 (2)	−0.0017 (17)	−0.0161 (16)	0.0013 (16)
C26	0.039 (2)	0.080 (3)	0.039 (2)	−0.001 (2)	−0.0113 (18)	0.007 (2)
C27	0.041 (2)	0.079 (3)	0.046 (2)	−0.003 (2)	−0.0213 (19)	0.008 (2)
C28	0.057 (3)	0.055 (3)	0.039 (2)	−0.007 (2)	−0.0247 (19)	0.0059 (19)
C29	0.049 (3)	0.070 (3)	0.033 (2)	−0.004 (2)	−0.0129 (18)	−0.0001 (19)
C30	0.036 (2)	0.056 (3)	0.029 (2)	0.0035 (19)	−0.0089 (16)	−0.0019 (18)
N1	0.0347 (17)	0.057 (2)	0.0264 (16)	0.0043 (15)	−0.0109 (13)	−0.0007 (14)
N2	0.0366 (18)	0.053 (2)	0.0303 (16)	−0.0001 (15)	−0.0145 (13)	0.0031 (14)
O1	0.0392 (16)	0.155 (3)	0.0299 (15)	0.0119 (18)	−0.0062 (12)	0.0033 (17)
O2	0.0388 (16)	0.141 (3)	0.0308 (14)	0.0113 (17)	−0.0064 (12)	0.0106 (17)

Geometric parameters (Å, º) top

C1—O1	1.351 (4)	C16—C17	1.404 (4)
C1—C6	1.385 (5)	C17—C18	1.391 (4)
C1—C2	1.393 (5)	C17—H17	0.9300
C2—C3	1.358 (5)	C18—C19	1.392 (5)
C2—H2A	0.9300	C18—C23	1.508 (4)
C3—C4	1.365 (5)	C19—C20	1.393 (5)
C3—H3	0.9300	C19—N2	1.447 (4)
C4—C5	1.384 (5)	C20—C21	1.398 (4)
C4—H4	0.9300	C20—C22	1.502 (5)
C5—C6	1.386 (5)	C21—H21	0.9300
C5—H5	0.9300	C22—H22A	0.9600
C6—C7	1.467 (4)	C22—H22B	0.9600
C7—N1	1.273 (4)	C22—H22C	0.9600
C7—H7	0.9300	C23—H23A	0.9600
C8—C13	1.398 (5)	C23—H23B	0.9600
C8—C9	1.400 (5)	C23—H23C	0.9600
C8—N1	1.441 (4)	C24—N2	1.274 (4)
C9—C10	1.400 (4)	C24—C25	1.460 (4)
C9—C15	1.504 (5)	C24—H24	0.9300
C10—C11	1.393 (4)	C25—C30	1.389 (5)
C10—H10	0.9300	C25—C26	1.401 (5)
C11—C12	1.395 (5)	C26—C27	1.381 (5)
C11—C16	1.496 (4)	C26—H26	0.9300
C12—C13	1.405 (4)	C27—C28	1.370 (5)
C12—H12	0.9300	C27—H27	0.9300
C13—C14	1.512 (5)	C28—C29	1.381 (5)
C14—H14A	0.9600	C28—H28	0.9300
C14—H14B	0.9600	C29—C30	1.389 (5)
C14—H14C	0.9600	C29—H29	0.9300
C15—H15A	0.9600	C30—O2	1.357 (4)
C15—H15B	0.9600	O1—H1	0.8200
C15—H15C	0.9600	O2—H2	0.8200
C16—C21	1.383 (4)

O1—C1—C6	121.5 (3)	C17—C16—C11	120.5 (3)
O1—C1—C2	118.7 (3)	C18—C17—C16	121.9 (3)
C6—C1—C2	119.8 (4)	C18—C17—H17	119.1
C3—C2—C1	119.9 (4)	C16—C17—H17	119.1
C3—C2—H2A	120.1	C17—C18—C19	117.8 (3)
C1—C2—H2A	120.1	C17—C18—C23	121.1 (3)
C2—C3—C4	121.6 (4)	C19—C18—C23	121.1 (3)
C2—C3—H3	119.2	C18—C19—C20	122.5 (3)
C4—C3—H3	119.2	C18—C19—N2	117.3 (3)
C3—C4—C5	118.9 (4)	C20—C19—N2	120.0 (3)
C3—C4—H4	120.6	C19—C20—C21	117.3 (3)
C5—C4—H4	120.6	C19—C20—C22	122.1 (3)
C4—C5—C6	121.0 (4)	C21—C20—C22	120.5 (3)
C4—C5—H5	119.5	C16—C21—C20	122.5 (3)
C6—C5—H5	119.5	C16—C21—H21	118.7
C1—C6—C5	118.8 (3)	C20—C21—H21	118.7
C1—C6—C7	121.8 (3)	C20—C22—H22A	109.5
C5—C6—C7	119.3 (3)	C20—C22—H22B	109.5
N1—C7—C6	122.1 (3)	H22A—C22—H22B	109.5
N1—C7—H7	118.9	C20—C22—H22C	109.5
C6—C7—H7	118.9	H22A—C22—H22C	109.5
C13—C8—C9	122.0 (3)	H22B—C22—H22C	109.5
C13—C8—N1	116.1 (3)	C18—C23—H23A	109.5
C9—C8—N1	121.7 (3)	C18—C23—H23B	109.5
C10—C9—C8	117.4 (3)	H23A—C23—H23B	109.5
C10—C9—C15	119.6 (3)	C18—C23—H23C	109.5
C8—C9—C15	122.9 (3)	H23A—C23—H23C	109.5
C11—C10—C9	122.8 (3)	H23B—C23—H23C	109.5
C11—C10—H10	118.6	N2—C24—C25	122.0 (3)
C9—C10—H10	118.6	N2—C24—H24	119.0
C10—C11—C12	117.9 (3)	C25—C24—H24	119.0
C10—C11—C16	122.0 (3)	C30—C25—C26	118.0 (3)
C12—C11—C16	119.9 (3)	C30—C25—C24	121.9 (3)
C11—C12—C13	121.7 (4)	C26—C25—C24	120.0 (3)
C11—C12—H12	119.2	C27—C26—C25	121.0 (4)
C13—C12—H12	119.2	C27—C26—H26	119.5
C8—C13—C12	118.2 (3)	C25—C26—H26	119.5
C8—C13—C14	121.4 (3)	C28—C27—C26	119.5 (4)
C12—C13—C14	120.3 (3)	C28—C27—H27	120.2
C13—C14—H14A	109.5	C26—C27—H27	120.2
C13—C14—H14B	109.5	C27—C28—C29	121.3 (4)
H14A—C14—H14B	109.5	C27—C28—H28	119.3
C13—C14—H14C	109.5	C29—C28—H28	119.3
H14A—C14—H14C	109.5	C28—C29—C30	118.9 (4)
H14B—C14—H14C	109.5	C28—C29—H29	120.5
C9—C15—H15A	109.5	C30—C29—H29	120.5
C9—C15—H15B	109.5	O2—C30—C29	117.7 (3)
H15A—C15—H15B	109.5	O2—C30—C25	121.1 (3)
C9—C15—H15C	109.5	C29—C30—C25	121.2 (4)
H15A—C15—H15C	109.5	C7—N1—C8	120.7 (3)
H15B—C15—H15C	109.5	C24—N2—C19	120.5 (3)
C21—C16—C17	117.9 (3)	C1—O1—H1	109.5
C21—C16—C11	121.5 (3)	C30—O2—H2	109.5

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O1—H1···N1	0.82	1.89	2.616 (3)	147
O2—H2···N2	0.82	1.89	2.609 (2)	146

Experimental details

Crystal data
Chemical formula	C₃₀H₂₈N₂O₂
M_r	448.54
Crystal system, space group	Monoclinic, P2₁/c
Temperature (K)	273
a, b, c (Å)	10.693 (5), 12.896 (6), 17.673 (8)
β (°)	90.871 (9)
V (Å³)	2436.7 (19)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.08
Crystal size (mm)	0.12 × 0.09 × 0.06

Data collection
Diffractometer	Bruker SMART CCD area-detector diffractometer
Absorption correction	–
No. of measured, independent and observed [I > 2σ(I)] reflections	12159, 4289, 1897
R_int	0.102
(sin θ/λ)_max (Å⁻¹)	0.595

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.064, 0.173, 0.93
No. of reflections	4289
No. of parameters	314
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.23, −0.21

Computer programs: SMART (Bruker, 1997), SAINT (Bruker, 1997), SAINT, SHELXS97 (Sheldrick, 1997), SHELXL97 (Sheldrick, 1997), SHELXTL (Bruker, 1998), SHELXTL.

Selected geometric parameters (Å, º) top

C1—O1	1.351 (4)	C19—N2	1.447 (4)
C6—C7	1.467 (4)	C24—N2	1.274 (4)
C7—N1	1.273 (4)	C24—C25	1.460 (4)
C8—N1	1.441 (4)	C30—O2	1.357 (4)

C7—N1—C8	120.7 (3)	C24—N2—C19	120.5 (3)