3-(Anthracen-9-yl­methyl­ene)-2,4-di­methyl-3H-benzo­[1,5]­diazepine

Megzari, A.; El Bali, B.; Janati, T.; Kerbal, A.; Benlarbi, N.; Benhadda, T.; Mimouni, M.; Bolte, M.

doi:10.1107/S1600536803007207

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3-(Anthracen-9-ylmethylene)-2,4-dimethyl-3H-benzo[1,5]diazepine

A. Megzari, B. El Bali, T. Janati, A. Kerbal, N. Benlarbi, T. Benhadda, M. Mimouni and M. Bolte

The title compound, C₂₆H₂₀N₂, crystallizes with two almost identical molecules in the asymmetric unit. The diazepine ring adopts a boat conformation.

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Supporting information

	Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536803007207/ob6229sup1.cif Contains datablocks I, global
	Structure factor file (CIF format) https://doi.org/10.1107/S1600536803007207/ob6229Isup2.hkl Contains datablock I

CCDC reference: 214596

checkCIF report

Key indicators

Single-crystal X-ray study
T = 173 K
Mean (C-C) = 0.004 Å
R factor = 0.051
wR factor = 0.123
Data-to-parameter ratio = 10.4

checkCIF results

No syntax errors found

ADDSYM reports no extra symmetry

General Notes



REFLT_03
         From the CIF: _diffrn_reflns_theta_max           29.45
         From the CIF: _reflns_number_total               5318
         Count of symmetry unique reflns         5366
         Completeness (_total/calc)             99.11%
         TEST3: Check Friedels for noncentro structure
         Estimate of Friedel pairs measured         0
         Fraction of Friedel pairs measured     0.000
         Are heavy atom types Z>Si present           no
          Please check that the estimate of the number of Friedel pairs is
          correct. If it is not, please give the correct count in the
          _publ_section_exptl_refinement section of the submitted CIF.

Comment top

Charge-transfer processes are fundamental in photosynthesis. They are important in the solar field, as well as in biochemical reactions. We synthesized a new donor–acceptor system based on anthracene connected by a double bond (Elazami et al., 1999; Senhaji et al., 2001), as it is the case with 1,4-benzodiazepine (Tucker et al., 1996). Our focus is the study of different intramolecular interactions in this system by the techniques of absorption and fluorescence spectroscopy. The synthesis of the title compound, (I), was performed by reacting 3-(anthracen-9-ylmethylene)pentane-2,4-dione and 1,2-diaminobenzene in ethanol (see Scheme).

(I) has a high stability at room temperature, its structure has been determined by IR, MS and NMR (¹H and ¹³C) spectroscopy. Since these techniques did not provide sufficient information about the conformation of the reaction product, we have carried out the X-ray structure analysis. (I) crystallizes with two almost identical molecules in the asymmetric unit. A least-squares fit of all non-H atoms of the two molecules gives an r.m.s. deviation of 0.075 Å. The diazepine ring adopts the boat conformation with the two N atoms and atoms C1 and C8 in a common plane. Atom C9 is the bow atom and C2 and C7 are the stern atoms.

Experimental top

Equimolar quantities of 3-(anthracen-9-ylmethylene)pentane-2,4-dione (2.88 g, 10 mmol) and benzene-1,2-diamine (1.1 g, 10 mmol) in 30 ml of ethanol were added to a 100 ml three-necked flask fitted with a reflux condenser. The mixture was stirred and refluxed for 12 h. The solution was filtered and extracted with diethyl ether (50 ml). The solvent was removed using a rotary evaporator. The residue was recrystallized from methanol leading to yellow crystals of the title compound (I).

Computing details top

Data collection: X-AREA (Stoe & Cie, 2001); cell refinement: X-AREA; data reduction: X-AREA; program(s) used to solve structure: SHELXS97 (Sheldrick, 1990); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: XP in SHELXTL-Plus (Sheldrick, 1991).

Figures top

	Fig. 1. Perspective view of molecule 1 in the asymmetric unit of the title compound with the atom numbering; displacement ellipsoids are at the 50% probability level.
	Fig. 2. Perspective view of molecule 2 in the asymmetric unit of the title compound with the atom numbering; displacement ellipsoids are at the 50% probability level.

3-(Anthracen-9-ylmethylene)-2,4-dimethyl-3H-benzo[1,5]diazepine top

Crystal data top

C₂₆H₂₀N₂	F(000) = 1520
M_r = 360.44	D_x = 1.261 Mg m⁻³
Orthorhombic, Pca2₁	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2c -2ac	Cell parameters from 24219 reflections
a = 12.8014 (9) Å	θ = 2.3–29.5°
b = 10.4027 (8) Å	µ = 0.07 mm⁻¹
c = 28.5030 (19) Å	T = 173 K
V = 3795.7 (5) Å³	Block, yellow
Z = 8	0.48 × 0.42 × 0.36 mm

Data collection top

Stoe IPDS II two-circle diffractometer	3581 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	R_int = 0.072
Graphite monochromator	θ_max = 29.5°, θ_min = 2.0°
ω scans	h = −17→17
31816 measured reflections	k = −14→14
5318 independent reflections	l = −39→39

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)] = 0.051	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.123	H-atom parameters constrained
S = 0.94	w = 1/[σ²(F_o²) + (0.0732P)²] where P = (F_o² + 2F_c²)/3
5318 reflections	(Δ/σ)_max < 0.001
509 parameters	Δρ_max = 0.37 e Å⁻³
1 restraint	Δρ_min = −0.20 e Å⁻³

Crystal data top

C₂₆H₂₀N₂	V = 3795.7 (5) Å³
M_r = 360.44	Z = 8
Orthorhombic, Pca2₁	Mo Kα radiation
a = 12.8014 (9) Å	µ = 0.07 mm⁻¹
b = 10.4027 (8) Å	T = 173 K
c = 28.5030 (19) Å	0.48 × 0.42 × 0.36 mm

Data collection top

Stoe IPDS II two-circle diffractometer	3581 reflections with I > 2σ(I)
31816 measured reflections	R_int = 0.072
5318 independent reflections

Refinement top

R[F² > 2σ(F²)] = 0.051	1 restraint
wR(F²) = 0.123	H-atom parameters constrained
S = 0.94	Δρ_max = 0.37 e Å⁻³
5318 reflections	Δρ_min = −0.20 e Å⁻³
509 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	0.7256 (2)	0.2535 (3)	0.31711 (11)	0.0421 (6)
C11	0.7918 (2)	0.1376 (3)	0.32798 (12)	0.0486 (7)
H11A	0.8433	0.1599	0.3521	0.073*
H11B	0.8279	0.1095	0.2995	0.073*
H11C	0.7471	0.0679	0.3395	0.073*
N1	0.73906 (19)	0.3576 (3)	0.33934 (9)	0.0447 (6)
C2	0.6766 (2)	0.4677 (3)	0.33082 (11)	0.0425 (6)
C3	0.7270 (2)	0.5862 (3)	0.33433 (12)	0.0492 (8)
H3	0.7995	0.5882	0.3414	0.059*
C4	0.6746 (3)	0.7001 (3)	0.32789 (15)	0.0553 (8)
H4	0.7108	0.7796	0.3298	0.066*
C5	0.5677 (3)	0.6976 (4)	0.31855 (14)	0.0548 (9)
H5	0.5309	0.7758	0.3135	0.066*
C6	0.5159 (2)	0.5837 (3)	0.31661 (12)	0.0479 (7)
H6	0.4425	0.5838	0.3117	0.058*
C7	0.5683 (2)	0.4652 (3)	0.32166 (11)	0.0420 (6)
N2	0.50422 (18)	0.3544 (3)	0.31998 (9)	0.0436 (6)
C8	0.5360 (2)	0.2482 (3)	0.30143 (11)	0.0430 (6)
C81	0.4648 (2)	0.1340 (3)	0.30096 (14)	0.0529 (8)
H81A	0.3975	0.1575	0.3149	0.079*
H81B	0.4964	0.0641	0.3192	0.079*
H81C	0.4541	0.1056	0.2685	0.079*
C9	0.64264 (19)	0.2345 (3)	0.28102 (11)	0.0388 (6)
C10	0.6604 (2)	0.2030 (3)	0.23631 (11)	0.0398 (6)
H10	0.6018	0.1841	0.2171	0.048*
C12	0.7661 (2)	0.1955 (3)	0.21462 (10)	0.0375 (6)
C13	0.8293 (2)	0.3063 (3)	0.21119 (10)	0.0382 (6)
C14	0.7951 (2)	0.4319 (3)	0.22533 (11)	0.0426 (6)
H14	0.7259	0.4422	0.2369	0.051*
C15	0.8584 (3)	0.5369 (3)	0.22271 (12)	0.0488 (7)
H15	0.8342	0.6186	0.2329	0.059*
C16	0.9618 (3)	0.5226 (3)	0.20453 (13)	0.0532 (8)
H16	1.0062	0.5956	0.2026	0.064*
C17	0.9972 (3)	0.4081 (3)	0.19012 (12)	0.0501 (7)
H17	1.0665	0.4015	0.1785	0.060*
C18	0.9332 (2)	0.2956 (3)	0.19179 (11)	0.0422 (6)
C19	0.9687 (2)	0.1767 (3)	0.17597 (12)	0.0451 (7)
H19	1.0376	0.1699	0.1638	0.054*
C20	0.9057 (2)	0.0673 (3)	0.17746 (10)	0.0405 (6)
C21	0.9395 (3)	−0.0532 (3)	0.15912 (13)	0.0493 (8)
H21	1.0069	−0.0596	0.1453	0.059*
C22	0.8773 (3)	−0.1594 (3)	0.16101 (13)	0.0537 (8)
H22	0.9005	−0.2383	0.1478	0.064*
C23	0.7786 (3)	−0.1519 (3)	0.18248 (13)	0.0521 (8)
H23	0.7365	−0.2269	0.1844	0.063*
C24	0.7420 (2)	−0.0397 (3)	0.20049 (11)	0.0466 (7)
H24	0.6752	−0.0378	0.2150	0.056*
C25	0.8026 (2)	0.0756 (3)	0.19792 (10)	0.0397 (6)
C1A	0.50427 (19)	0.7544 (3)	0.44258 (10)	0.0394 (6)
C11A	0.4380 (2)	0.6387 (3)	0.43185 (12)	0.0489 (7)
H11D	0.3879	0.6602	0.4071	0.073*
H11E	0.4002	0.6126	0.4602	0.073*
H11F	0.4828	0.5680	0.4213	0.073*
N1A	0.48963 (17)	0.8598 (2)	0.42022 (9)	0.0419 (5)
C2A	0.5522 (2)	0.9689 (3)	0.42852 (11)	0.0424 (7)
C3A	0.5016 (2)	1.0884 (3)	0.42478 (12)	0.0499 (8)
H3A	0.4297	1.0899	0.4166	0.060*
C4A	0.5524 (3)	1.2044 (4)	0.43261 (15)	0.0582 (10)
H4A	0.5151	1.2834	0.4323	0.070*
C5A	0.6601 (3)	1.2017 (3)	0.44095 (14)	0.0549 (8)
H5A	0.6972	1.2797	0.4457	0.066*
C6A	0.7123 (2)	1.0856 (3)	0.44226 (13)	0.0491 (8)
H6A	0.7860	1.0858	0.4465	0.059*
C7A	0.6610 (2)	0.9685 (3)	0.43762 (11)	0.0422 (6)
N2A	0.72538 (18)	0.8577 (3)	0.43847 (10)	0.0455 (6)
C8A	0.6950 (2)	0.7534 (3)	0.45686 (11)	0.0403 (6)
C81A	0.7657 (2)	0.6373 (3)	0.45711 (13)	0.0515 (8)
H81D	0.8321	0.6591	0.4420	0.077*
H81E	0.7322	0.5668	0.4400	0.077*
H81F	0.7787	0.6106	0.4896	0.077*
C9A	0.58861 (19)	0.7361 (3)	0.47836 (11)	0.0380 (6)
C10A	0.5732 (2)	0.7058 (2)	0.52284 (10)	0.0384 (6)
H10A	0.6330	0.6898	0.5417	0.046*
C12A	0.4685 (2)	0.6949 (3)	0.54555 (10)	0.0384 (6)
C13A	0.4029 (2)	0.8029 (3)	0.55062 (10)	0.0400 (6)
C14A	0.4317 (2)	0.9291 (3)	0.53486 (11)	0.0438 (7)
H14A	0.4997	0.9431	0.5225	0.053*
C15A	0.3636 (2)	1.0289 (3)	0.53722 (12)	0.0490 (7)
H15A	0.3839	1.1110	0.5258	0.059*
C16A	0.2627 (3)	1.0121 (3)	0.55660 (14)	0.0534 (8)
H16A	0.2156	1.0825	0.5575	0.064*
C17A	0.2328 (2)	0.8965 (3)	0.57387 (12)	0.0484 (7)
H17A	0.1659	0.8875	0.5879	0.058*
C18A	0.3014 (2)	0.7875 (3)	0.57116 (11)	0.0436 (6)
C19A	0.2708 (2)	0.6671 (3)	0.58774 (11)	0.0447 (6)
H19A	0.2045	0.6586	0.6024	0.054*
C20A	0.3343 (2)	0.5592 (3)	0.58343 (11)	0.0438 (7)
C21A	0.3003 (3)	0.4341 (3)	0.59705 (11)	0.0468 (7)
H21A	0.2341	0.4244	0.6117	0.056*
C22A	0.3602 (3)	0.3289 (3)	0.58957 (12)	0.0522 (8)
H22A	0.3356	0.2465	0.5987	0.063*
C23A	0.4600 (2)	0.3415 (3)	0.56804 (13)	0.0524 (8)
H23A	0.5020	0.2674	0.5631	0.063*
C24A	0.4955 (3)	0.4585 (3)	0.55458 (12)	0.0463 (7)
H24A	0.5624	0.4650	0.5404	0.056*
C25A	0.4351 (2)	0.5719 (3)	0.56124 (10)	0.0404 (6)

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
C1	0.0327 (13)	0.0528 (17)	0.0408 (16)	−0.0030 (12)	0.0001 (11)	0.0033 (13)
C11	0.0453 (15)	0.0552 (18)	0.0453 (17)	0.0082 (13)	−0.0050 (13)	0.0008 (14)
N1	0.0377 (12)	0.0565 (15)	0.0398 (14)	0.0044 (12)	−0.0018 (10)	−0.0042 (12)
C2	0.0362 (12)	0.0496 (16)	0.0417 (17)	0.0021 (11)	0.0017 (11)	−0.0062 (13)
C3	0.0364 (14)	0.061 (2)	0.0505 (19)	0.0020 (14)	0.0046 (13)	−0.0134 (16)
C4	0.0522 (17)	0.0472 (17)	0.066 (2)	−0.0069 (14)	0.0098 (16)	−0.0146 (16)
C5	0.0510 (17)	0.055 (2)	0.059 (2)	0.0131 (16)	0.0031 (15)	−0.0155 (18)
C6	0.0404 (14)	0.0540 (19)	0.0494 (18)	0.0080 (13)	0.0039 (13)	−0.0109 (15)
C7	0.0367 (13)	0.0534 (17)	0.0358 (16)	0.0024 (12)	0.0044 (11)	−0.0024 (14)
N2	0.0333 (11)	0.0502 (14)	0.0473 (15)	−0.0005 (10)	0.0022 (10)	−0.0037 (12)
C8	0.0324 (12)	0.0503 (17)	0.0462 (17)	−0.0015 (12)	−0.0011 (11)	−0.0009 (13)
C81	0.0401 (14)	0.0551 (18)	0.063 (2)	−0.0069 (14)	0.0030 (14)	−0.0013 (16)
C9	0.0328 (12)	0.0379 (14)	0.0456 (16)	0.0002 (10)	0.0003 (11)	−0.0011 (12)
C10	0.0367 (12)	0.0382 (13)	0.0447 (16)	0.0004 (11)	−0.0038 (11)	−0.0044 (12)
C12	0.0391 (13)	0.0401 (14)	0.0332 (14)	−0.0006 (11)	−0.0045 (11)	−0.0005 (11)
C13	0.0398 (13)	0.0405 (14)	0.0343 (14)	0.0001 (11)	−0.0039 (11)	0.0006 (11)
C14	0.0470 (15)	0.0408 (14)	0.0401 (16)	0.0050 (12)	−0.0003 (12)	−0.0001 (12)
C15	0.0619 (18)	0.0394 (14)	0.0452 (18)	−0.0082 (14)	−0.0019 (14)	0.0043 (14)
C16	0.0622 (18)	0.0496 (17)	0.048 (2)	−0.0151 (15)	0.0014 (15)	0.0018 (15)
C17	0.0487 (16)	0.0538 (18)	0.0477 (17)	−0.0080 (14)	0.0069 (13)	0.0029 (14)
C18	0.0445 (14)	0.0441 (15)	0.0380 (15)	−0.0008 (12)	0.0031 (11)	0.0001 (12)
C19	0.0405 (13)	0.0535 (17)	0.0413 (16)	0.0042 (12)	0.0029 (12)	0.0001 (13)
C20	0.0453 (14)	0.0404 (15)	0.0357 (14)	0.0082 (11)	−0.0030 (12)	0.0014 (12)
C21	0.0502 (16)	0.0474 (17)	0.0504 (19)	0.0132 (13)	−0.0044 (14)	−0.0043 (14)
C22	0.0609 (18)	0.0419 (15)	0.058 (2)	0.0131 (14)	−0.0127 (15)	−0.0115 (14)
C23	0.0575 (18)	0.0382 (15)	0.061 (2)	0.0008 (13)	−0.0169 (15)	−0.0051 (14)
C24	0.0446 (14)	0.0474 (16)	0.0480 (18)	−0.0009 (13)	−0.0080 (13)	−0.0034 (14)
C25	0.0444 (14)	0.0410 (15)	0.0337 (14)	0.0066 (12)	−0.0075 (12)	−0.0025 (12)
C1A	0.0300 (11)	0.0492 (15)	0.0391 (15)	−0.0010 (11)	0.0022 (10)	−0.0021 (12)
C11A	0.0449 (15)	0.0563 (18)	0.0456 (17)	−0.0088 (13)	−0.0045 (13)	−0.0014 (14)
N1A	0.0321 (10)	0.0518 (14)	0.0416 (13)	0.0020 (10)	−0.0002 (9)	0.0011 (11)
C2A	0.0364 (13)	0.0530 (17)	0.0378 (16)	0.0028 (12)	0.0031 (11)	0.0096 (14)
C3A	0.0379 (14)	0.060 (2)	0.0518 (19)	0.0111 (14)	0.0019 (13)	0.0102 (15)
C4A	0.0445 (16)	0.060 (2)	0.070 (3)	0.0048 (15)	0.0115 (17)	0.0264 (18)
C5A	0.0474 (16)	0.0486 (17)	0.069 (2)	−0.0055 (14)	0.0053 (15)	0.0121 (16)
C6A	0.0347 (14)	0.057 (2)	0.055 (2)	−0.0004 (13)	0.0036 (13)	0.0096 (16)
C7A	0.0343 (12)	0.0484 (15)	0.0439 (16)	−0.0010 (11)	0.0036 (11)	0.0071 (14)
N2A	0.0347 (12)	0.0543 (16)	0.0475 (15)	0.0024 (11)	0.0018 (10)	0.0013 (13)
C8A	0.0312 (12)	0.0449 (16)	0.0447 (16)	0.0024 (11)	−0.0010 (11)	−0.0047 (13)
C81A	0.0398 (15)	0.0508 (16)	0.064 (2)	0.0057 (13)	0.0035 (14)	0.0046 (15)
C9A	0.0328 (12)	0.0365 (13)	0.0449 (16)	−0.0021 (10)	−0.0004 (11)	−0.0016 (12)
C10A	0.0334 (11)	0.0372 (13)	0.0446 (16)	0.0002 (10)	−0.0040 (11)	0.0020 (12)
C12A	0.0380 (13)	0.0401 (14)	0.0372 (15)	−0.0045 (11)	−0.0017 (11)	0.0010 (11)
C13A	0.0419 (13)	0.0427 (14)	0.0355 (15)	−0.0024 (12)	0.0010 (11)	−0.0031 (12)
C14A	0.0469 (15)	0.0447 (16)	0.0397 (16)	−0.0022 (13)	0.0013 (12)	0.0004 (13)
C15A	0.0580 (17)	0.0425 (15)	0.0466 (18)	0.0017 (13)	0.0026 (14)	−0.0033 (14)
C16A	0.0586 (17)	0.0496 (18)	0.052 (2)	0.0109 (15)	0.0051 (15)	−0.0078 (14)
C17A	0.0455 (15)	0.0540 (17)	0.0455 (16)	0.0035 (13)	0.0062 (13)	−0.0075 (14)
C18A	0.0435 (14)	0.0489 (15)	0.0382 (15)	0.0029 (12)	0.0018 (12)	−0.0072 (13)
C19A	0.0458 (15)	0.0509 (16)	0.0374 (15)	−0.0071 (12)	0.0067 (12)	−0.0013 (13)
C20A	0.0418 (14)	0.0478 (16)	0.0418 (17)	−0.0064 (12)	−0.0024 (12)	0.0013 (13)
C21A	0.0485 (15)	0.0522 (17)	0.0397 (16)	−0.0139 (13)	−0.0022 (12)	0.0055 (13)
C22A	0.0653 (19)	0.0449 (16)	0.0465 (18)	−0.0118 (15)	−0.0092 (15)	0.0089 (13)
C23A	0.0536 (16)	0.0464 (17)	0.057 (2)	0.0004 (14)	−0.0091 (15)	0.0046 (14)
C24A	0.0463 (15)	0.0436 (16)	0.0489 (18)	0.0022 (13)	−0.0051 (13)	0.0001 (14)
C25A	0.0405 (13)	0.0432 (15)	0.0374 (15)	−0.0036 (11)	−0.0047 (11)	0.0050 (12)

Geometric parameters (Å, º) top

C1—N1	1.266 (4)	C1A—N1A	1.282 (4)
C1—C9	1.492 (4)	C1A—C9A	1.497 (4)
C1—C11	1.505 (4)	C1A—C11A	1.504 (4)
C11—H11A	0.9800	C11A—H11D	0.9800
C11—H11B	0.9800	C11A—H11E	0.9800
C11—H11C	0.9800	C11A—H11F	0.9800
N1—C2	1.417 (4)	N1A—C2A	1.409 (4)
C2—C3	1.395 (4)	C2A—C3A	1.407 (4)
C2—C7	1.411 (4)	C2A—C7A	1.417 (4)
C3—C4	1.373 (5)	C3A—C4A	1.389 (5)
C3—H3	0.9500	C3A—H3A	0.9500
C4—C5	1.395 (5)	C4A—C5A	1.399 (5)
C4—H4	0.9500	C4A—H4A	0.9500
C5—C6	1.359 (5)	C5A—C6A	1.381 (5)
C5—H5	0.9500	C5A—H5A	0.9500
C6—C7	1.411 (4)	C6A—C7A	1.390 (4)
C6—H6	0.9500	C6A—H6A	0.9500
C7—N2	1.416 (4)	C7A—N2A	1.417 (4)
N2—C8	1.291 (4)	N2A—C8A	1.267 (4)
C8—C9	1.491 (4)	C8A—C9A	1.504 (4)
C8—C81	1.497 (4)	C8A—C81A	1.509 (4)
C81—H81A	0.9800	C81A—H81D	0.9800
C81—H81B	0.9800	C81A—H81E	0.9800
C81—H81C	0.9800	C81A—H81F	0.9800
C9—C10	1.335 (4)	C9A—C10A	1.321 (4)
C10—C12	1.489 (4)	C10A—C12A	1.493 (4)
C10—H10	0.9500	C10A—H10A	0.9500
C12—C13	1.412 (4)	C12A—C13A	1.410 (4)
C12—C25	1.415 (4)	C12A—C25A	1.421 (4)
C13—C14	1.436 (4)	C13A—C18A	1.435 (4)
C13—C18	1.444 (4)	C13A—C14A	1.436 (4)
C14—C15	1.362 (4)	C14A—C15A	1.357 (4)
C14—H14	0.9500	C14A—H14A	0.9500
C15—C16	1.429 (5)	C15A—C16A	1.416 (5)
C15—H15	0.9500	C15A—H15A	0.9500
C16—C17	1.338 (5)	C16A—C17A	1.354 (5)
C16—H16	0.9500	C16A—H16A	0.9500
C17—C18	1.430 (4)	C17A—C18A	1.437 (4)
C17—H17	0.9500	C17A—H17A	0.9500
C18—C19	1.393 (4)	C18A—C19A	1.394 (4)
C19—C20	1.395 (4)	C19A—C20A	1.392 (4)
C19—H19	0.9500	C19A—H19A	0.9500
C20—C21	1.426 (4)	C20A—C21A	1.427 (4)
C20—C25	1.445 (4)	C20A—C25A	1.443 (4)
C21—C22	1.363 (5)	C21A—C22A	1.353 (5)
C21—H21	0.9500	C21A—H21A	0.9500
C22—C23	1.406 (5)	C22A—C23A	1.424 (5)
C22—H22	0.9500	C22A—H22A	0.9500
C23—C24	1.357 (4)	C23A—C24A	1.355 (5)
C23—H23	0.9500	C23A—H23A	0.9500
C24—C25	1.431 (4)	C24A—C25A	1.424 (4)
C24—H24	0.9500	C24A—H24A	0.9500

N1—C1—C9	123.7 (3)	N1A—C1A—C9A	123.6 (2)
N1—C1—C11	120.4 (3)	N1A—C1A—C11A	120.1 (3)
C9—C1—C11	115.9 (3)	C9A—C1A—C11A	116.3 (3)
C1—C11—H11A	109.5	C1A—C11A—H11D	109.5
C1—C11—H11B	109.5	C1A—C11A—H11E	109.5
H11A—C11—H11B	109.5	H11D—C11A—H11E	109.5
C1—C11—H11C	109.5	C1A—C11A—H11F	109.5
H11A—C11—H11C	109.5	H11D—C11A—H11F	109.5
H11B—C11—H11C	109.5	H11E—C11A—H11F	109.5
C1—N1—C2	121.9 (3)	C1A—N1A—C2A	121.5 (2)
C3—C2—C7	118.9 (3)	N1A—C2A—C3A	115.9 (2)
C3—C2—N1	116.2 (2)	N1A—C2A—C7A	126.0 (3)
C7—C2—N1	124.8 (3)	C3A—C2A—C7A	118.0 (3)
C4—C3—C2	121.8 (3)	C4A—C3A—C2A	122.7 (3)
C4—C3—H3	119.1	C4A—C3A—H3A	118.6
C2—C3—H3	119.1	C2A—C3A—H3A	118.6
C3—C4—C5	119.3 (3)	C3A—C4A—C5A	118.1 (3)
C3—C4—H4	120.4	C3A—C4A—H4A	120.9
C5—C4—H4	120.4	C5A—C4A—H4A	120.9
C6—C5—C4	120.2 (3)	C6A—C5A—C4A	120.0 (3)
C6—C5—H5	119.9	C6A—C5A—H5A	120.0
C4—C5—H5	119.9	C4A—C5A—H5A	120.0
C5—C6—C7	121.7 (3)	C5A—C6A—C7A	122.3 (3)
C5—C6—H6	119.1	C5A—C6A—H6A	118.8
C7—C6—H6	119.1	C7A—C6A—H6A	118.8
C6—C7—N2	115.6 (2)	C6A—C7A—C2A	118.7 (3)
C6—C7—C2	118.1 (3)	C6A—C7A—N2A	115.9 (2)
N2—C7—C2	126.2 (3)	C2A—C7A—N2A	125.2 (3)
C8—N2—C7	121.9 (2)	C8A—N2A—C7A	121.7 (2)
N2—C8—C9	122.0 (3)	N2A—C8A—C9A	123.3 (3)
N2—C8—C81	119.4 (3)	N2A—C8A—C81A	120.2 (3)
C9—C8—C81	118.5 (3)	C9A—C8A—C81A	116.5 (3)
C8—C81—H81A	109.5	C8A—C81A—H81D	109.5
C8—C81—H81B	109.5	C8A—C81A—H81E	109.5
H81A—C81—H81B	109.5	H81D—C81A—H81E	109.5
C8—C81—H81C	109.5	C8A—C81A—H81F	109.5
H81A—C81—H81C	109.5	H81D—C81A—H81F	109.5
H81B—C81—H81C	109.5	H81E—C81A—H81F	109.5
C10—C9—C1	124.7 (2)	C10A—C9A—C1A	125.2 (2)
C10—C9—C8	123.5 (3)	C10A—C9A—C8A	123.7 (3)
C1—C9—C8	111.7 (3)	C1A—C9A—C8A	111.1 (2)
C9—C10—C12	124.3 (2)	C9A—C10A—C12A	124.6 (2)
C9—C10—H10	117.8	C9A—C10A—H10A	117.7
C12—C10—H10	117.8	C12A—C10A—H10A	117.7
C13—C12—C25	120.5 (3)	C13A—C12A—C25A	120.4 (2)
C13—C12—C10	120.5 (2)	C13A—C12A—C10A	121.2 (2)
C25—C12—C10	119.1 (2)	C25A—C12A—C10A	118.4 (2)
C12—C13—C14	123.2 (3)	C12A—C13A—C18A	119.5 (3)
C12—C13—C18	119.4 (2)	C12A—C13A—C14A	123.0 (3)
C14—C13—C18	117.3 (3)	C18A—C13A—C14A	117.5 (3)
C15—C14—C13	122.1 (3)	C15A—C14A—C13A	121.3 (3)
C15—C14—H14	118.9	C15A—C14A—H14A	119.3
C13—C14—H14	118.9	C13A—C14A—H14A	119.3
C14—C15—C16	119.2 (3)	C14A—C15A—C16A	120.7 (3)
C14—C15—H15	120.4	C14A—C15A—H15A	119.7
C16—C15—H15	120.4	C16A—C15A—H15A	119.7
C17—C16—C15	121.2 (3)	C17A—C16A—C15A	120.7 (3)
C17—C16—H16	119.4	C17A—C16A—H16A	119.7
C15—C16—H16	119.4	C15A—C16A—H16A	119.7
C16—C17—C18	121.6 (3)	C16A—C17A—C18A	120.5 (3)
C16—C17—H17	119.2	C16A—C17A—H17A	119.7
C18—C17—H17	119.2	C18A—C17A—H17A	119.7
C19—C18—C17	122.0 (3)	C19A—C18A—C13A	119.6 (3)
C19—C18—C13	119.5 (3)	C19A—C18A—C17A	121.3 (3)
C17—C18—C13	118.5 (3)	C13A—C18A—C17A	119.2 (3)
C18—C19—C20	121.7 (3)	C20A—C19A—C18A	122.0 (3)
C18—C19—H19	119.1	C20A—C19A—H19A	119.0
C20—C19—H19	119.1	C18A—C19A—H19A	119.0
C19—C20—C21	122.0 (3)	C19A—C20A—C21A	122.2 (3)
C19—C20—C25	119.4 (3)	C19A—C20A—C25A	119.2 (3)
C21—C20—C25	118.5 (3)	C21A—C20A—C25A	118.4 (3)
C22—C21—C20	121.4 (3)	C22A—C21A—C20A	121.5 (3)
C22—C21—H21	119.3	C22A—C21A—H21A	119.3
C20—C21—H21	119.3	C20A—C21A—H21A	119.3
C21—C22—C23	119.8 (3)	C21A—C22A—C23A	120.2 (3)
C21—C22—H22	120.1	C21A—C22A—H22A	119.9
C23—C22—H22	120.1	C23A—C22A—H22A	119.9
C24—C23—C22	121.5 (3)	C24A—C23A—C22A	120.4 (3)
C24—C23—H23	119.3	C24A—C23A—H23A	119.8
C22—C23—H23	119.3	C22A—C23A—H23A	119.8
C23—C24—C25	121.0 (3)	C23A—C24A—C25A	121.6 (3)
C23—C24—H24	119.5	C23A—C24A—H24A	119.2
C25—C24—H24	119.5	C25A—C24A—H24A	119.2
C12—C25—C24	122.9 (3)	C12A—C25A—C24A	122.7 (3)
C12—C25—C20	119.4 (3)	C12A—C25A—C20A	119.3 (3)
C24—C25—C20	117.8 (3)	C24A—C25A—C20A	118.0 (3)

C9—C1—N1—C2	−1.5 (5)	C9A—C1A—N1A—C2A	−1.1 (4)
C11—C1—N1—C2	−178.5 (3)	C11A—C1A—N1A—C2A	−178.2 (3)
C1—N1—C2—C3	−144.6 (3)	C1A—N1A—C2A—C3A	−145.6 (3)
C1—N1—C2—C7	38.7 (5)	C1A—N1A—C2A—C7A	38.0 (4)
C7—C2—C3—C4	−1.7 (5)	N1A—C2A—C3A—C4A	179.0 (3)
N1—C2—C3—C4	−178.6 (3)	C7A—C2A—C3A—C4A	−4.3 (5)
C2—C3—C4—C5	1.4 (5)	C2A—C3A—C4A—C5A	5.1 (5)
C3—C4—C5—C6	1.0 (6)	C3A—C4A—C5A—C6A	−1.4 (6)
C4—C5—C6—C7	−3.0 (5)	C4A—C5A—C6A—C7A	−2.9 (6)
C5—C6—C7—N2	178.6 (3)	C5A—C6A—C7A—C2A	3.7 (5)
C5—C6—C7—C2	2.6 (5)	C5A—C6A—C7A—N2A	178.4 (3)
C3—C2—C7—C6	−0.2 (4)	N1A—C2A—C7A—C6A	176.1 (3)
N1—C2—C7—C6	176.3 (3)	C3A—C2A—C7A—C6A	−0.2 (4)
C3—C2—C7—N2	−175.7 (3)	N1A—C2A—C7A—N2A	2.0 (5)
N1—C2—C7—N2	0.8 (5)	C3A—C2A—C7A—N2A	−174.3 (3)
C6—C7—N2—C8	145.1 (3)	C6A—C7A—N2A—C8A	145.0 (3)
C2—C7—N2—C8	−39.3 (5)	C2A—C7A—N2A—C8A	−40.7 (5)
C7—N2—C8—C9	0.7 (5)	C7A—N2A—C8A—C9A	1.3 (5)
C7—N2—C8—C81	179.6 (3)	C7A—N2A—C8A—C81A	−180.0 (3)
N1—C1—C9—C10	120.6 (3)	N1A—C1A—C9A—C10A	120.0 (3)
C11—C1—C9—C10	−62.3 (4)	C11A—C1A—C9A—C10A	−62.7 (4)
N1—C1—C9—C8	−62.4 (4)	N1A—C1A—C9A—C8A	−61.5 (4)
C11—C1—C9—C8	114.7 (3)	C11A—C1A—C9A—C8A	115.8 (3)
N2—C8—C9—C10	−120.8 (3)	N2A—C8A—C9A—C10A	−119.5 (4)
C81—C8—C9—C10	60.3 (4)	C81A—C8A—C9A—C10A	61.7 (4)
N2—C8—C9—C1	62.1 (4)	N2A—C8A—C9A—C1A	61.9 (4)
C81—C8—C9—C1	−116.8 (3)	C81A—C8A—C9A—C1A	−116.8 (3)
C1—C9—C10—C12	−6.7 (4)	C1A—C9A—C10A—C12A	−5.0 (4)
C8—C9—C10—C12	176.6 (3)	C8A—C9A—C10A—C12A	176.7 (3)
C9—C10—C12—C13	−63.1 (4)	C9A—C10A—C12A—C13A	−65.0 (4)
C9—C10—C12—C25	116.3 (3)	C9A—C10A—C12A—C25A	113.8 (3)
C25—C12—C13—C14	176.8 (3)	C25A—C12A—C13A—C18A	−0.9 (4)
C10—C12—C13—C14	−3.8 (4)	C10A—C12A—C13A—C18A	177.8 (3)
C25—C12—C13—C18	−1.9 (4)	C25A—C12A—C13A—C14A	−179.1 (3)
C10—C12—C13—C18	177.4 (3)	C10A—C12A—C13A—C14A	−0.4 (4)
C12—C13—C14—C15	178.4 (3)	C12A—C13A—C14A—C15A	175.2 (3)
C18—C13—C14—C15	−2.8 (4)	C18A—C13A—C14A—C15A	−3.1 (5)
C13—C14—C15—C16	1.2 (5)	C13A—C14A—C15A—C16A	1.8 (5)
C14—C15—C16—C17	−0.1 (5)	C14A—C15A—C16A—C17A	1.1 (6)
C15—C16—C17—C18	0.7 (6)	C15A—C16A—C17A—C18A	−2.5 (5)
C16—C17—C18—C19	178.6 (3)	C12A—C13A—C18A—C19A	2.8 (4)
C16—C17—C18—C13	−2.3 (5)	C14A—C13A—C18A—C19A	−178.8 (3)
C12—C13—C18—C19	1.2 (4)	C12A—C13A—C18A—C17A	−176.6 (3)
C14—C13—C18—C19	−177.7 (3)	C14A—C13A—C18A—C17A	1.7 (4)
C12—C13—C18—C17	−177.9 (3)	C16A—C17A—C18A—C19A	−178.4 (3)
C14—C13—C18—C17	3.3 (4)	C16A—C17A—C18A—C13A	1.1 (5)
C17—C18—C19—C20	−179.7 (3)	C13A—C18A—C19A—C20A	−2.5 (5)
C13—C18—C19—C20	1.3 (5)	C17A—C18A—C19A—C20A	177.0 (3)
C18—C19—C20—C21	176.7 (3)	C18A—C19A—C20A—C21A	−175.1 (3)
C18—C19—C20—C25	−3.0 (5)	C18A—C19A—C20A—C25A	0.1 (5)
C19—C20—C21—C22	179.7 (3)	C19A—C20A—C21A—C22A	175.3 (3)
C25—C20—C21—C22	−0.6 (5)	C25A—C20A—C21A—C22A	0.0 (5)
C20—C21—C22—C23	−1.7 (5)	C20A—C21A—C22A—C23A	0.5 (5)
C21—C22—C23—C24	1.8 (5)	C21A—C22A—C23A—C24A	−0.5 (5)
C22—C23—C24—C25	0.5 (5)	C22A—C23A—C24A—C25A	−0.2 (5)
C13—C12—C25—C24	180.0 (3)	C13A—C12A—C25A—C24A	176.3 (3)
C10—C12—C25—C24	0.6 (4)	C10A—C12A—C25A—C24A	−2.4 (4)
C13—C12—C25—C20	0.3 (4)	C13A—C12A—C25A—C20A	−1.5 (4)
C10—C12—C25—C20	−179.1 (3)	C10A—C12A—C25A—C20A	179.8 (3)
C23—C24—C25—C12	177.6 (3)	C23A—C24A—C25A—C12A	−177.1 (3)
C23—C24—C25—C20	−2.7 (4)	C23A—C24A—C25A—C20A	0.7 (5)
C19—C20—C25—C12	2.1 (4)	C19A—C20A—C25A—C12A	1.9 (4)
C21—C20—C25—C12	−177.5 (3)	C21A—C20A—C25A—C12A	177.3 (3)
C19—C20—C25—C24	−177.6 (3)	C19A—C20A—C25A—C24A	−176.0 (3)
C21—C20—C25—C24	2.8 (4)	C21A—C20A—C25A—C24A	−0.6 (4)

Experimental details

Crystal data
Chemical formula	C₂₆H₂₀N₂
M_r	360.44
Crystal system, space group	Orthorhombic, Pca2₁
Temperature (K)	173
a, b, c (Å)	12.8014 (9), 10.4027 (8), 28.5030 (19)
V (Å³)	3795.7 (5)
Z	8
Radiation type	Mo Kα
µ (mm⁻¹)	0.07
Crystal size (mm)	0.48 × 0.42 × 0.36

Data collection
Diffractometer	Stoe IPDS II two-circle diffractometer
Absorption correction	–
No. of measured, independent and observed [I > 2σ(I)] reflections	31816, 5318, 3581
R_int	0.072
(sin θ/λ)_max (Å⁻¹)	0.692

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.051, 0.123, 0.94
No. of reflections	5318
No. of parameters	509
No. of restraints	1
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.37, −0.20

Computer programs: X-AREA (Stoe & Cie, 2001), X-AREA, SHELXS97 (Sheldrick, 1990), SHELXL97 (Sheldrick, 1997), XP in SHELXTL-Plus (Sheldrick, 1991).

Selected geometric parameters (Å, º) top

C1—N1	1.266 (4)	C1A—C9A	1.497 (4)
N1—C2	1.417 (4)	N1A—C2A	1.409 (4)
C2—C7	1.411 (4)	C2A—C7A	1.417 (4)
C7—N2	1.416 (4)	C7A—N2A	1.417 (4)
N2—C8	1.291 (4)	N2A—C8A	1.267 (4)
C8—C9	1.491 (4)	C8A—C9A	1.504 (4)
C1A—N1A	1.282 (4)

C1—N1—C2—C7	38.7 (5)	C1A—N1A—C2A—C7A	38.0 (4)
C2—C7—N2—C8	−39.3 (5)	C2A—C7A—N2A—C8A	−40.7 (5)
N1—C1—C9—C8	−62.4 (4)	N1A—C1A—C9A—C8A	−61.5 (4)
N2—C8—C9—C1	62.1 (4)	N2A—C8A—C9A—C1A	61.9 (4)

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