(E)-1-(3,4-Dimethyl­benzyl­idene)-2,2-diphenyl­hydrazine

Mendoza, A.; Cabrera-Vivas, B.M.; Meléndrez-Luevano, R.; Ramírez, J.C.; Flores-Alamo, M.

doi:10.1107/S1600536811015352

organic compounds

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ISSN: 2056-9890

Volume 67| Part 6| June 2011| Page o1287

doi:10.1107/S1600536811015352

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(E)-1-(3,4-Dimethylbenzylidene)-2,2-diphenylhydrazine

Angel Mendoza,^a ^* Blanca M. Cabrera-Vivas,^b Ruth Meléndrez-Luevano,^b Juan C. Ramírez ^b and Marcos Flores-Alamo ^c

^aCentro de Química, ICUAP, Benemérita Universidad Autónoma de Puebla, Puebla, Pue., Mexico, ^bFacultad de Ciencias Químicas, Benemérita Universidad Autónoma de Puebla, Puebla, Pue., Mexico, and ^cFacultad de Química, Universidad Nacional Autónoma de México, 04510 México DF, Mexico
^*Correspondence e-mail: angel.mendoza.m@gmail.com

(Received 10 April 2011; accepted 23 April 2011; online 7 May 2011)

The asymmetric unit of the title compound, C₂₁H₂₀N₂, contain two molecules, both of them showing an E configuration of the C=N bond. The dihedral angles between the phenyl rings in the phenylhydrazone groups are 86.84 (10) and 84.85 (8)° for the two molecules. Intermolecular C—H⋯π interactions are observed in the crystal structure.

Related literature

For applications of hydrazones, see: Angell et al. (2006 ); Buss et al. (2004 ); Melnyk et al. (2006 ); Ranford et al. (1998 ). For related structures see: Clulow et al. (2008 ); Mendoza et al. (2010 ).

Experimental

Crystal data

C₂₁H₂₀N₂
M_r = 300.39
Triclinic, $[P \overline 1]$
a = 9.9375 (5) Å
b = 10.6322 (5) Å
c = 17.5680 (8) Å
α = 77.530 (4)°
β = 76.480 (4)°
γ = 77.074 (4)°
V = 1732.60 (14) Å³
Z = 4
Mo Kα radiation
μ = 0.07 mm⁻¹
T = 293 K
0.61 × 0.42 × 0.27 mm

Data collection

Oxford Diffraction Xcalibur Atlas Gemini diffractometer
Absorption correction: analytical (CrysAlis PRO; Oxford Diffraction, 2009 $[Oxford Diffraction (2009). CrysAlis CCD, CrysAlis PRO and CrysAlis RED. Oxford Diffraction Ltd, Yarnton, England.]$ ) T_min = 0.971, T_max = 0.984
12246 measured reflections
6288 independent reflections
3202 reflections with I > 2σ(I)
R_int = 0.027

Refinement

R[F² > 2σ(F²)] = 0.040
wR(F²) = 0.100
S = 0.85
6288 reflections
420 parameters
H-atom parameters constrained
Δρ_max = 0.15 e Å⁻³
Δρ_min = −0.11 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

Cg1, Cg2, Cg3 and Cg4 are the centroids of the C31–C36, C37–C42, C2–C7 and C23–C28 rings, respectively.

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C3—H3⋯Cg1ⁱ	0.93	2.81	3.7152 (18)	166
C6—H6⋯Cg1ⁱⁱ	0.93	2.66	3.5506 (19)	160
C9—H9C⋯Cg2ⁱⁱⁱ	0.96	2.97	3.7170 (19)	136
C29—H29B⋯Cg3^iv	0.96	3.00	3.931 (2)	165
C41—H41⋯Cg4ⁱ	0.93	2.83	3.590 (2)	139
Symmetry codes: (i) -x+1, -y, -z; (ii) -x, -y+1, -z; (iii) x, y+1, z; (iv) x, y-1, z.

Data collection: CrysAlis CCD (Oxford Diffraction, 2009 $[Oxford Diffraction (2009). CrysAlis CCD, CrysAlis PRO and CrysAlis RED. Oxford Diffraction Ltd, Yarnton, England.]$ ); cell refinement: CrysAlis RED (Oxford Diffraction, 2009 $[Oxford Diffraction (2009). CrysAlis CCD, CrysAlis PRO and CrysAlis RED. Oxford Diffraction Ltd, Yarnton, England.]$ ); data reduction: CrysAlis RED; 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 ).

Supporting information

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536811015352/bt5512sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536811015352/bt5512Isup2.hkl

checkCIF report

Comment top

Many applications are known for hydrazones and their derivatives in the chemical analysis field. Employing these compounds as molecular sensors in determination and quantization of aldehydes and ketones in gas currents allows their use in environmental, biological and industrial applications (Angell, et al. 2006). Hydrazones have been used in the treatment of several diseases as malaria (Melnyk et al., 2006) or genetic disorders (Ranford et al., 1998). Coordination compounds with iron have shown therapeutic attributes in the treatment of cancer (Buss et al., 2004).

The title compound I, C₂₁H₂₀N₂, presents an E configuration of the C=N double bond. The asymmetric unit contains two non-planar molecules. The dihedral angles between the C10/C11/C12/C13/C14/C15 ring and C16/C17/C18/C19/C20/C21 ring is 86.84 (10)° for molecule 1 (N1 to C21). The dihedral angle for the phenyl rings C31/C32/C33/C34/C35/C36 and C37/C38/C39/C40/C41/C42 is 84.85 (8)° for molecule 2 (N3 to C42). The dimethyl-phenyl rings are slightly twisted with respect to the C=N group with torsion angles of 2.8 (2)° for N1/C1/C2/C7 and of 1.1 (2)° for N3/C22/C23/C24. The N—N distances [N1—N2 1.3765 (17) Å and N3—N4 1.3701 (16) Å] are shorter than found in free diphenylhydrazine [1.418 (2) Å] (Clulow, et al., 2008). The imine bond distances [N1—C1 1.277 (2) Å and N3—C22 1.2797 (18) Å] are longer than N=C typical bond and shorter [1.287 (2) Å] than related structures with N,N-diphenylhidrazone group (Mendoza et al. 2010). Intermolecular C—H···π interactions are observed.

Related literature top

For applications of hydrazones, see: Angell et al. (2006); Buss et al. (2004); Melnyk et al. (2006); Ranford et al. (1998). For related structures see: Clulow et al. (2008); Mendoza et al. (2010).

Experimental top

N,N-diphenylhydrazine (592 mg, 2.68 mmol) was dissolved in ethanol and acetic acid (0.5 ml) was added slowly into this solution while stirring. 300 mg (2.24 mmol) of 3,4-dimethylbenzaldehyde was added drop by drop into the above solution with strong stirring and the resulting mixture was kept at atmospheric temperature until it became amber transparent solution. After three hours the amber solution turns to be precipitated. The mixture was separated with filtration in vacuum system and the precipitate was washed three times with cold methanol. Recrystallization was performed several times with acetonitrile, to obtain colorless crystals for X-ray analysis. Yield 72% at 25°C, m. p. 95–99°C. UV λ_max = 341.24 nm. FT. IR (film): (cm^-1): 3033 ν(C—H), 2933 ν(C—H), 1588, 1490 ν(C=N), 1221 ν(C=N—N). ¹H NMR (400 MHz (CD₃)₂CO: (δ p.p.m.): 7.46–7.41 (m, 4H), 7.37 (s, 1H), 7.35–7.32 (dd, 1H), 7.22–7.16 (m, 6H), 7.13 (s, 1H), 7.10–7.08 (d, 1H), 2.23, 2.21 (2 s, 6H). ¹³C NMR (400 MHz, (CD₃)₂CO: (δ p.p.m.): 143.83, 136.72, 136.56, 135.72, 133.90, 129.84, 129.77, 127.45, 124.41, 123.78, 122.35, 18.91, 18.81. MS—EI: m/z = 300 M⁺.

Computing details top

Data collection: CrysAlis CCD (Oxford Diffraction, 2009); cell refinement: CrysAlis RED (Oxford Diffraction, 2009); data reduction: CrysAlis RED (Oxford Diffraction, 2009); 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).

Figures top

Fig. 1. The molecular structure and the atom labelling scheme for I. Displacement ellipsoids are draw at the 50% probability level and H atoms are shown as circles of arbitrary size.

(E)-1-(3,4-Dimethylbenzylidene)-2,2-diphenylhydrazine top

Crystal data top

C₂₁H₂₀N₂	Z = 4
M_r = 300.39	F(000) = 640
Triclinic, P1	D_x = 1.152 Mg m⁻³
a = 9.9375 (5) Å	Mo Kα radiation, λ = 0.71073 Å
b = 10.6322 (5) Å	Cell parameters from 3720 reflections
c = 17.5680 (8) Å	θ = 3.4–25.2°
α = 77.530 (4)°	µ = 0.07 mm⁻¹
β = 76.480 (4)°	T = 293 K
γ = 77.074 (4)°	Prism, colorless
V = 1732.60 (14) Å³	0.61 × 0.42 × 0.27 mm

Data collection top

Oxford Diffraction Xcalibur Atlas Gemini diffractometer	6288 independent reflections
Graphite monochromator	3202 reflections with I > 2σ(I)
Detector resolution: 10.4685 pixels mm^-1	R_int = 0.027
ω scans	θ_max = 25.3°, θ_min = 3.4°
Absorption correction: analytical (CrysAlis PRO; Oxford Diffraction, 2009)	h = −9→11
T_min = 0.971, T_max = 0.984	k = −10→12
12246 measured reflections	l = −21→20

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)] = 0.040	H-atom parameters constrained
wR(F²) = 0.100	w = 1/[σ²(F_o²) + (0.0496P)²] where P = (F_o² + 2F_c²)/3
S = 0.85	(Δ/σ)_max = 0.001
6288 reflections	Δρ_max = 0.15 e Å⁻³
420 parameters	Δρ_min = −0.11 e Å⁻³
0 restraints	Extinction correction: SHELXL97 (Sheldrick, 2008), Fc^*=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.0220 (12)

Crystal data top

C₂₁H₂₀N₂	γ = 77.074 (4)°
M_r = 300.39	V = 1732.60 (14) Å³
Triclinic, P1	Z = 4
a = 9.9375 (5) Å	Mo Kα radiation
b = 10.6322 (5) Å	µ = 0.07 mm⁻¹
c = 17.5680 (8) Å	T = 293 K
α = 77.530 (4)°	0.61 × 0.42 × 0.27 mm
β = 76.480 (4)°

Data collection top

Oxford Diffraction Xcalibur Atlas Gemini diffractometer	6288 independent reflections
Absorption correction: analytical (CrysAlis PRO; Oxford Diffraction, 2009)	3202 reflections with I > 2σ(I)
T_min = 0.971, T_max = 0.984	R_int = 0.027
12246 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.040	0 restraints
wR(F²) = 0.100	H-atom parameters constrained
S = 0.85	Δρ_max = 0.15 e Å⁻³
6288 reflections	Δρ_min = −0.11 e Å⁻³
420 parameters

Special details top

Geometry. All s.u.'s (except the s.u. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell s.u.'s are taken into account individually in the estimation of s.u.'s in distances, angles and torsion angles; correlations between s.u.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell s.u.'s is used for estimating s.u.'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 > 2σ(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
N1	0.36159 (15)	0.39399 (14)	0.36518 (8)	0.0660 (4)
N2	0.41791 (15)	0.32889 (15)	0.43054 (8)	0.0756 (4)
C16	0.32092 (19)	0.29285 (16)	0.49984 (10)	0.0597 (4)
C21	0.1779 (2)	0.33547 (18)	0.50422 (11)	0.0730 (5)
H21	0.1443	0.3888	0.4607	0.088*
C20	0.0850 (2)	0.2992 (2)	0.57287 (12)	0.0858 (6)
H20	−0.0111	0.3292	0.5752	0.103*
C19	0.1307 (3)	0.2199 (2)	0.63774 (12)	0.0875 (6)
H19	0.0669	0.1956	0.6837	0.105*
C18	0.2719 (3)	0.17699 (19)	0.63365 (11)	0.0812 (6)
H18	0.3043	0.1226	0.6772	0.097*
C17	0.3673 (2)	0.21310 (18)	0.56583 (10)	0.0730 (5)
H17	0.4632	0.1838	0.5643	0.088*
C10	0.56693 (18)	0.29103 (18)	0.42665 (9)	0.0601 (5)
C11	0.6403 (2)	0.37197 (19)	0.44503 (11)	0.0787 (6)
H11	0.5936	0.4524	0.4589	0.094*
C12	0.7826 (3)	0.3344 (3)	0.44297 (12)	0.0907 (6)
H12	0.8317	0.3887	0.4563	0.109*
C13	0.8510 (2)	0.2186 (3)	0.42167 (12)	0.0936 (7)
H13	0.9472	0.1932	0.4204	0.112*
C14	0.7801 (3)	0.1397 (2)	0.40227 (13)	0.0963 (7)
H14	0.8281	0.0604	0.3873	0.116*
C15	0.6372 (2)	0.1753 (2)	0.40443 (11)	0.0806 (6)
H15	0.5891	0.1204	0.3908	0.097*
C1	0.44210 (18)	0.43109 (16)	0.29977 (10)	0.0617 (5)
H1	0.5391	0.4145	0.2964	0.074*
C2	0.38244 (17)	0.49919 (15)	0.23059 (9)	0.0532 (4)
C7	0.23891 (17)	0.52161 (16)	0.23122 (10)	0.0606 (5)
H7	0.1774	0.4926	0.2771	0.073*
C6	0.18753 (17)	0.58661 (16)	0.16420 (10)	0.0617 (5)
H6	0.0913	0.5999	0.1656	0.074*
C5	0.27467 (16)	0.63270 (15)	0.09501 (9)	0.0513 (4)
C4	0.41897 (16)	0.61329 (15)	0.09341 (9)	0.0518 (4)
C3	0.46939 (16)	0.54615 (16)	0.16103 (10)	0.0572 (4)
H3	0.5657	0.532	0.1597	0.069*
C8	0.51750 (17)	0.66410 (19)	0.01989 (10)	0.0770 (5)
H8A	0.613	0.6321	0.0267	0.115*
H8B	0.4992	0.7581	0.0111	0.115*
H8C	0.5032	0.6345	−0.025	0.115*
C9	0.21465 (17)	0.70064 (17)	0.02243 (10)	0.0686 (5)
H9A	0.1143	0.7069	0.0346	0.103*
H9B	0.2544	0.6513	−0.0199	0.103*
H9C	0.2371	0.7869	0.0063	0.103*
N3	0.19466 (12)	0.19292 (13)	0.00863 (7)	0.0525 (3)
N4	0.19869 (13)	0.19943 (13)	−0.07059 (7)	0.0565 (4)
C31	0.18030 (15)	0.32507 (16)	−0.11695 (9)	0.0477 (4)
C32	0.13244 (15)	0.43680 (16)	−0.08245 (9)	0.0522 (4)
H32	0.1149	0.4297	−0.0275	0.063*
C33	0.11102 (16)	0.55796 (17)	−0.12972 (10)	0.0599 (4)
H33	0.0781	0.6322	−0.106	0.072*
C34	0.13712 (17)	0.57179 (18)	−0.21115 (11)	0.0657 (5)
H34	0.1215	0.6542	−0.2424	0.079*
C35	0.18661 (18)	0.46180 (19)	−0.24540 (10)	0.0663 (5)
H35	0.2056	0.4698	−0.3005	0.08*
C36	0.20849 (17)	0.33961 (17)	−0.19914 (9)	0.0600 (4)
H36	0.2426	0.266	−0.2233	0.072*
C37	0.23353 (16)	0.08491 (15)	−0.10724 (8)	0.0492 (4)
C38	0.12895 (17)	0.03792 (17)	−0.12529 (10)	0.0587 (4)
H38	0.0355	0.078	−0.1116	0.07*
C39	0.1620 (2)	−0.06805 (18)	−0.16345 (10)	0.0681 (5)
H39	0.091	−0.0988	−0.1763	0.082*
C40	0.2989 (2)	−0.12838 (17)	−0.18261 (10)	0.0704 (5)
H40	0.3213	−0.2002	−0.2084	0.084*
C41	0.4032 (2)	−0.08287 (19)	−0.16375 (10)	0.0749 (5)
H41	0.4963	−0.1245	−0.1763	0.09*
C42	0.37124 (17)	0.02402 (18)	−0.12631 (10)	0.0648 (5)
H42	0.4425	0.055	−0.1139	0.078*
C22	0.21859 (15)	0.08199 (17)	0.05388 (9)	0.0532 (4)
H22	0.2346	0.0053	0.0333	0.064*
C23	0.22101 (14)	0.07456 (16)	0.13727 (9)	0.0479 (4)
C28	0.24973 (16)	−0.04682 (16)	0.18511 (9)	0.0544 (4)
H28	0.2625	−0.1219	0.1633	0.065*
C27	0.26025 (16)	−0.06090 (16)	0.26412 (9)	0.0572 (4)
C26	0.23930 (16)	0.05158 (17)	0.29740 (9)	0.0575 (4)
C25	0.20856 (17)	0.17242 (17)	0.25014 (10)	0.0628 (5)
H25	0.1929	0.2477	0.2722	0.075*
C24	0.20038 (16)	0.18513 (16)	0.17172 (10)	0.0591 (5)
H24	0.181	0.2681	0.1416	0.071*
C29	0.2983 (2)	−0.19570 (18)	0.31134 (11)	0.0935 (7)
H29A	0.393	−0.2085	0.3194	0.14*
H29B	0.2911	−0.2606	0.2827	0.14*
H29C	0.235	−0.2038	0.3619	0.14*
C30	0.2536 (2)	0.0441 (2)	0.38198 (10)	0.0887 (6)
H30A	0.2308	0.1307	0.3948	0.133*
H30B	0.3486	0.0058	0.3876	0.133*
H30C	0.1904	−0.0089	0.4173	0.133*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
N1	0.0642 (9)	0.0726 (10)	0.0561 (9)	−0.0088 (7)	−0.0201 (8)	0.0053 (8)
N2	0.0601 (10)	0.0977 (12)	0.0557 (9)	−0.0060 (8)	−0.0172 (8)	0.0129 (8)
C16	0.0683 (12)	0.0599 (12)	0.0512 (11)	−0.0110 (9)	−0.0159 (10)	−0.0064 (9)
C21	0.0701 (13)	0.0872 (15)	0.0601 (12)	−0.0164 (10)	−0.0175 (10)	−0.0020 (10)
C20	0.0763 (13)	0.1129 (18)	0.0689 (14)	−0.0269 (12)	−0.0096 (12)	−0.0118 (13)
C19	0.1008 (18)	0.1049 (18)	0.0549 (13)	−0.0310 (13)	−0.0027 (12)	−0.0107 (12)
C18	0.1102 (18)	0.0804 (15)	0.0494 (12)	−0.0108 (13)	−0.0185 (12)	−0.0072 (10)
C17	0.0839 (13)	0.0763 (14)	0.0545 (12)	−0.0046 (10)	−0.0190 (11)	−0.0067 (10)
C10	0.0620 (12)	0.0657 (13)	0.0489 (10)	−0.0040 (10)	−0.0170 (9)	−0.0029 (9)
C11	0.0801 (15)	0.0813 (15)	0.0751 (13)	−0.0075 (12)	−0.0145 (11)	−0.0223 (11)
C12	0.0837 (17)	0.115 (2)	0.0818 (15)	−0.0300 (14)	−0.0284 (12)	−0.0101 (14)
C13	0.0675 (14)	0.121 (2)	0.0756 (15)	−0.0010 (15)	−0.0203 (11)	0.0084 (14)
C14	0.0977 (19)	0.0835 (17)	0.0968 (17)	0.0175 (14)	−0.0238 (14)	−0.0222 (13)
C15	0.0903 (16)	0.0723 (15)	0.0818 (14)	−0.0036 (12)	−0.0299 (12)	−0.0158 (11)
C1	0.0564 (11)	0.0663 (12)	0.0590 (11)	−0.0090 (9)	−0.0171 (9)	0.0007 (9)
C2	0.0523 (10)	0.0510 (11)	0.0562 (10)	−0.0111 (8)	−0.0165 (9)	−0.0005 (8)
C7	0.0534 (11)	0.0666 (12)	0.0596 (11)	−0.0198 (8)	−0.0100 (9)	0.0021 (9)
C6	0.0472 (10)	0.0696 (12)	0.0693 (12)	−0.0165 (8)	−0.0196 (9)	0.0009 (10)
C5	0.0527 (10)	0.0492 (10)	0.0564 (10)	−0.0152 (8)	−0.0194 (9)	−0.0025 (8)
C4	0.0519 (10)	0.0519 (11)	0.0541 (10)	−0.0164 (8)	−0.0148 (8)	−0.0020 (8)
C3	0.0451 (9)	0.0667 (12)	0.0603 (11)	−0.0117 (8)	−0.0192 (9)	−0.0011 (9)
C8	0.0620 (12)	0.1005 (15)	0.0667 (12)	−0.0268 (10)	−0.0176 (10)	0.0070 (11)
C9	0.0655 (11)	0.0738 (13)	0.0696 (12)	−0.0174 (9)	−0.0294 (9)	0.0034 (9)
N3	0.0526 (8)	0.0588 (10)	0.0472 (8)	−0.0148 (6)	−0.0124 (6)	−0.0035 (7)
N4	0.0715 (9)	0.0548 (10)	0.0448 (8)	−0.0116 (7)	−0.0162 (7)	−0.0065 (7)
C31	0.0430 (9)	0.0545 (11)	0.0468 (10)	−0.0125 (7)	−0.0134 (7)	−0.0023 (8)
C32	0.0488 (10)	0.0586 (12)	0.0495 (10)	−0.0082 (8)	−0.0143 (8)	−0.0066 (9)
C33	0.0588 (11)	0.0573 (12)	0.0652 (12)	−0.0074 (8)	−0.0224 (9)	−0.0065 (9)
C34	0.0697 (12)	0.0599 (13)	0.0661 (13)	−0.0175 (9)	−0.0227 (10)	0.0079 (10)
C35	0.0762 (13)	0.0729 (14)	0.0484 (10)	−0.0223 (10)	−0.0131 (9)	0.0024 (10)
C36	0.0689 (11)	0.0618 (12)	0.0499 (11)	−0.0145 (9)	−0.0128 (9)	−0.0071 (9)
C37	0.0480 (10)	0.0512 (10)	0.0454 (9)	−0.0084 (8)	−0.0091 (8)	−0.0029 (8)
C38	0.0478 (10)	0.0633 (12)	0.0664 (11)	−0.0100 (8)	−0.0120 (8)	−0.0128 (9)
C39	0.0707 (13)	0.0675 (13)	0.0717 (12)	−0.0191 (10)	−0.0167 (10)	−0.0142 (10)
C40	0.0905 (15)	0.0592 (13)	0.0564 (11)	−0.0060 (11)	−0.0071 (11)	−0.0150 (9)
C41	0.0582 (12)	0.0847 (15)	0.0670 (13)	0.0043 (10)	0.0001 (10)	−0.0133 (11)
C42	0.0472 (11)	0.0827 (14)	0.0636 (12)	−0.0117 (9)	−0.0085 (9)	−0.0132 (10)
C22	0.0523 (10)	0.0564 (12)	0.0525 (10)	−0.0151 (8)	−0.0115 (8)	−0.0063 (9)
C23	0.0423 (9)	0.0534 (11)	0.0471 (10)	−0.0100 (7)	−0.0103 (7)	−0.0034 (8)
C28	0.0608 (10)	0.0501 (11)	0.0550 (11)	−0.0140 (8)	−0.0135 (8)	−0.0085 (8)
C27	0.0596 (11)	0.0573 (12)	0.0528 (11)	−0.0108 (8)	−0.0156 (8)	−0.0004 (9)
C26	0.0565 (10)	0.0632 (12)	0.0516 (10)	−0.0047 (8)	−0.0154 (8)	−0.0081 (9)
C25	0.0686 (12)	0.0593 (12)	0.0596 (12)	0.0005 (9)	−0.0171 (9)	−0.0163 (9)
C24	0.0625 (11)	0.0524 (11)	0.0598 (11)	−0.0024 (8)	−0.0192 (9)	−0.0048 (9)
C29	0.1421 (19)	0.0656 (14)	0.0724 (13)	−0.0160 (12)	−0.0396 (13)	0.0063 (11)
C30	0.1113 (16)	0.0927 (16)	0.0646 (12)	−0.0006 (12)	−0.0351 (12)	−0.0180 (11)

Geometric parameters (Å, º) top

N1—C1	1.2773 (19)	N3—C22	1.2797 (18)
N1—N2	1.3765 (17)	N3—N4	1.3701 (16)
N2—C16	1.405 (2)	N4—C31	1.4041 (19)
N2—C10	1.434 (2)	N4—C37	1.4362 (18)
C16—C21	1.381 (2)	C31—C36	1.386 (2)
C16—C17	1.388 (2)	C31—C32	1.389 (2)
C21—C20	1.376 (2)	C32—C33	1.376 (2)
C21—H21	0.93	C32—H32	0.93
C20—C19	1.369 (3)	C33—C34	1.374 (2)
C20—H20	0.93	C33—H33	0.93
C19—C18	1.364 (3)	C34—C35	1.371 (2)
C19—H19	0.93	C34—H34	0.93
C18—C17	1.379 (2)	C35—C36	1.377 (2)
C18—H18	0.93	C35—H35	0.93
C17—H17	0.93	C36—H36	0.93
C10—C15	1.360 (2)	C37—C38	1.373 (2)
C10—C11	1.374 (2)	C37—C42	1.374 (2)
C11—C12	1.374 (3)	C38—C39	1.373 (2)
C11—H11	0.93	C38—H38	0.93
C12—C13	1.350 (3)	C39—C40	1.366 (2)
C12—H12	0.93	C39—H39	0.93
C13—C14	1.347 (3)	C40—C41	1.368 (2)
C13—H13	0.93	C40—H40	0.93
C14—C15	1.379 (3)	C41—C42	1.374 (2)
C14—H14	0.93	C41—H41	0.93
C15—H15	0.93	C42—H42	0.93
C1—C2	1.455 (2)	C22—C23	1.455 (2)
C1—H1	0.93	C22—H22	0.93
C2—C3	1.387 (2)	C23—C24	1.390 (2)
C2—C7	1.390 (2)	C23—C28	1.390 (2)
C7—C6	1.377 (2)	C28—C27	1.390 (2)
C7—H7	0.93	C28—H28	0.93
C6—C5	1.381 (2)	C27—C26	1.396 (2)
C6—H6	0.93	C27—C29	1.509 (2)
C5—C4	1.397 (2)	C26—C25	1.384 (2)
C5—C9	1.506 (2)	C26—C30	1.509 (2)
C4—C3	1.387 (2)	C25—C24	1.375 (2)
C4—C8	1.504 (2)	C25—H25	0.93
C3—H3	0.93	C24—H24	0.93
C8—H8A	0.96	C29—H29A	0.96
C8—H8B	0.96	C29—H29B	0.96
C8—H8C	0.96	C29—H29C	0.96
C9—H9A	0.96	C30—H30A	0.96
C9—H9B	0.96	C30—H30B	0.96
C9—H9C	0.96	C30—H30C	0.96

C1—N1—N2	120.22 (14)	C22—N3—N4	120.47 (13)
N1—N2—C16	116.03 (14)	N3—N4—C31	116.75 (12)
N1—N2—C10	122.07 (14)	N3—N4—C37	122.52 (13)
C16—N2—C10	121.73 (13)	C31—N4—C37	120.46 (12)
C21—C16—C17	118.38 (17)	C36—C31—C32	118.44 (15)
C21—C16—N2	121.21 (15)	C36—C31—N4	120.01 (15)
C17—C16—N2	120.41 (16)	C32—C31—N4	121.54 (14)
C20—C21—C16	120.14 (18)	C33—C32—C31	119.90 (15)
C20—C21—H21	119.9	C33—C32—H32	120
C16—C21—H21	119.9	C31—C32—H32	120
C19—C20—C21	121.4 (2)	C34—C33—C32	121.46 (16)
C19—C20—H20	119.3	C34—C33—H33	119.3
C21—C20—H20	119.3	C32—C33—H33	119.3
C18—C19—C20	118.7 (2)	C35—C34—C33	118.75 (16)
C18—C19—H19	120.7	C35—C34—H34	120.6
C20—C19—H19	120.7	C33—C34—H34	120.6
C19—C18—C17	120.99 (18)	C34—C35—C36	120.70 (16)
C19—C18—H18	119.5	C34—C35—H35	119.7
C17—C18—H18	119.5	C36—C35—H35	119.7
C18—C17—C16	120.36 (18)	C35—C36—C31	120.73 (16)
C18—C17—H17	119.8	C35—C36—H36	119.6
C16—C17—H17	119.8	C31—C36—H36	119.6
C15—C10—C11	119.31 (17)	C38—C37—C42	119.71 (15)
C15—C10—N2	120.53 (17)	C38—C37—N4	119.82 (13)
C11—C10—N2	120.16 (17)	C42—C37—N4	120.44 (14)
C10—C11—C12	120.12 (18)	C39—C38—C37	120.19 (15)
C10—C11—H11	119.9	C39—C38—H38	119.9
C12—C11—H11	119.9	C37—C38—H38	119.9
C13—C12—C11	120.0 (2)	C40—C39—C38	120.10 (17)
C13—C12—H12	120	C40—C39—H39	120
C11—C12—H12	120	C38—C39—H39	120
C14—C13—C12	120.2 (2)	C39—C40—C41	119.84 (17)
C14—C13—H13	119.9	C39—C40—H40	120.1
C12—C13—H13	119.9	C41—C40—H40	120.1
C13—C14—C15	120.7 (2)	C40—C41—C42	120.45 (16)
C13—C14—H14	119.7	C40—C41—H41	119.8
C15—C14—H14	119.7	C42—C41—H41	119.8
C10—C15—C14	119.66 (19)	C37—C42—C41	119.70 (16)
C10—C15—H15	120.2	C37—C42—H42	120.1
C14—C15—H15	120.2	C41—C42—H42	120.1
N1—C1—C2	120.15 (16)	N3—C22—C23	120.75 (15)
N1—C1—H1	119.9	N3—C22—H22	119.6
C2—C1—H1	119.9	C23—C22—H22	119.6
C3—C2—C7	117.54 (14)	C24—C23—C28	117.36 (14)
C3—C2—C1	120.02 (15)	C24—C23—C22	122.72 (15)
C7—C2—C1	122.44 (15)	C28—C23—C22	119.89 (15)
C6—C7—C2	120.26 (15)	C27—C28—C23	122.90 (15)
C6—C7—H7	119.9	C27—C28—H28	118.6
C2—C7—H7	119.9	C23—C28—H28	118.6
C7—C6—C5	121.94 (15)	C28—C27—C26	118.71 (15)
C7—C6—H6	119	C28—C27—C29	119.93 (15)
C5—C6—H6	119	C26—C27—C29	121.33 (15)
C6—C5—C4	118.81 (14)	C25—C26—C27	118.42 (14)
C6—C5—C9	120.28 (14)	C25—C26—C30	119.86 (16)
C4—C5—C9	120.90 (14)	C27—C26—C30	121.70 (16)
C3—C4—C5	118.58 (15)	C24—C25—C26	122.32 (16)
C3—C4—C8	120.75 (15)	C24—C25—H25	118.8
C5—C4—C8	120.67 (14)	C26—C25—H25	118.8
C4—C3—C2	122.85 (15)	C25—C24—C23	120.28 (15)
C4—C3—H3	118.6	C25—C24—H24	119.9
C2—C3—H3	118.6	C23—C24—H24	119.9
C4—C8—H8A	109.5	C27—C29—H29A	109.5
C4—C8—H8B	109.5	C27—C29—H29B	109.5
H8A—C8—H8B	109.5	H29A—C29—H29B	109.5
C4—C8—H8C	109.5	C27—C29—H29C	109.5
H8A—C8—H8C	109.5	H29A—C29—H29C	109.5
H8B—C8—H8C	109.5	H29B—C29—H29C	109.5
C5—C9—H9A	109.5	C26—C30—H30A	109.5
C5—C9—H9B	109.5	C26—C30—H30B	109.5
H9A—C9—H9B	109.5	H30A—C30—H30B	109.5
C5—C9—H9C	109.5	C26—C30—H30C	109.5
H9A—C9—H9C	109.5	H30A—C30—H30C	109.5
H9B—C9—H9C	109.5	H30B—C30—H30C	109.5

C1—N1—N2—C16	179.59 (15)	C22—N3—N4—C31	−175.97 (13)
C1—N1—N2—C10	−5.1 (2)	C22—N3—N4—C37	−1.9 (2)
N1—N2—C16—C21	−8.0 (2)	N3—N4—C31—C36	168.14 (13)
C10—N2—C16—C21	176.64 (17)	C37—N4—C31—C36	−6.0 (2)
N1—N2—C16—C17	172.04 (15)	N3—N4—C31—C32	−12.63 (19)
C10—N2—C16—C17	−3.3 (3)	C37—N4—C31—C32	173.21 (13)
C17—C16—C21—C20	0.2 (3)	C36—C31—C32—C33	1.5 (2)
N2—C16—C21—C20	−179.79 (16)	N4—C31—C32—C33	−177.73 (13)
C16—C21—C20—C19	−0.6 (3)	C31—C32—C33—C34	−0.6 (2)
C21—C20—C19—C18	0.3 (3)	C32—C33—C34—C35	−0.5 (2)
C20—C19—C18—C17	0.4 (3)	C33—C34—C35—C36	0.6 (2)
C19—C18—C17—C16	−0.8 (3)	C34—C35—C36—C31	0.3 (2)
C21—C16—C17—C18	0.5 (3)	C32—C31—C36—C35	−1.4 (2)
N2—C16—C17—C18	−179.52 (15)	N4—C31—C36—C35	177.86 (14)
N1—N2—C10—C15	−86.5 (2)	N3—N4—C37—C38	103.54 (17)
C16—N2—C10—C15	88.6 (2)	C31—N4—C37—C38	−82.65 (18)
N1—N2—C10—C11	93.2 (2)	N3—N4—C37—C42	−78.19 (18)
C16—N2—C10—C11	−91.7 (2)	C31—N4—C37—C42	95.62 (18)
C15—C10—C11—C12	−1.7 (3)	C42—C37—C38—C39	−1.1 (2)
N2—C10—C11—C12	178.59 (16)	N4—C37—C38—C39	177.16 (15)
C10—C11—C12—C13	1.0 (3)	C37—C38—C39—C40	0.9 (3)
C11—C12—C13—C14	0.1 (3)	C38—C39—C40—C41	−0.1 (3)
C12—C13—C14—C15	−0.5 (3)	C39—C40—C41—C42	−0.6 (3)
C11—C10—C15—C14	1.3 (3)	C38—C37—C42—C41	0.4 (2)
N2—C10—C15—C14	−178.98 (17)	N4—C37—C42—C41	−177.84 (15)
C13—C14—C15—C10	−0.2 (3)	C40—C41—C42—C37	0.5 (3)
N2—N1—C1—C2	179.62 (14)	N4—N3—C22—C23	177.09 (12)
N1—C1—C2—C3	176.21 (15)	N3—C22—C23—C24	−1.1 (2)
N1—C1—C2—C7	−2.8 (2)	N3—C22—C23—C28	−178.83 (13)
C3—C2—C7—C6	0.9 (2)	C24—C23—C28—C27	−0.9 (2)
C1—C2—C7—C6	179.98 (15)	C22—C23—C28—C27	176.88 (14)
C2—C7—C6—C5	−0.7 (2)	C23—C28—C27—C26	0.9 (2)
C7—C6—C5—C4	−0.4 (2)	C23—C28—C27—C29	−177.19 (15)
C7—C6—C5—C9	178.62 (14)	C28—C27—C26—C25	0.2 (2)
C6—C5—C4—C3	1.2 (2)	C29—C27—C26—C25	178.17 (16)
C9—C5—C4—C3	−177.80 (14)	C28—C27—C26—C30	−178.03 (16)
C6—C5—C4—C8	−178.79 (15)	C29—C27—C26—C30	0.0 (2)
C9—C5—C4—C8	2.2 (2)	C27—C26—C25—C24	−1.1 (2)
C5—C4—C3—C2	−1.0 (2)	C30—C26—C25—C24	177.13 (16)
C8—C4—C3—C2	179.01 (15)	C26—C25—C24—C23	1.0 (2)
C7—C2—C3—C4	−0.1 (2)	C28—C23—C24—C25	0.0 (2)
C1—C2—C3—C4	−179.15 (14)	C22—C23—C24—C25	−177.75 (14)

Hydrogen-bond geometry (Å, º) top

Cg1, Cg2, Cg3 and Cg4 are the centroids of the C31–C36, C37–C42, C2–C7 and C23–C28 rings, respectively.

D—H···A	D—H	H···A	D···A	D—H···A
C3—H3···Cg1ⁱ	0.93	2.81	3.7152 (18)	166
C6—H6···Cg1ⁱⁱ	0.93	2.66	3.5506 (19)	160
C9—H9C···Cg2ⁱⁱⁱ	0.96	2.97	3.7170 (19)	136
C29—H29B···Cg3^iv	0.96	3.00	3.931 (2)	165
C41—H41···Cg4ⁱ	0.93	2.83	3.590 (2)	139

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

Experimental details

Crystal data
Chemical formula	C₂₁H₂₀N₂
M_r	300.39
Crystal system, space group	Triclinic, P1
Temperature (K)	293
a, b, c (Å)	9.9375 (5), 10.6322 (5), 17.5680 (8)
α, β, γ (°)	77.530 (4), 76.480 (4), 77.074 (4)
V (Å³)	1732.60 (14)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.07
Crystal size (mm)	0.61 × 0.42 × 0.27

Data collection
Diffractometer	Oxford Diffraction Xcalibur Atlas Gemini diffractometer
Absorption correction	Analytical (CrysAlis PRO; Oxford Diffraction, 2009)
T_min, T_max	0.971, 0.984
No. of measured, independent and observed [I > 2σ(I)] reflections	12246, 6288, 3202
R_int	0.027
(sin θ/λ)_max (Å⁻¹)	0.601

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.040, 0.100, 0.85
No. of reflections	6288
No. of parameters	420
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.15, −0.11

Computer programs: CrysAlis CCD (Oxford Diffraction, 2009), CrysAlis RED (Oxford Diffraction, 2009), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), ORTEP-3 for Windows (Farrugia, 1997), WinGX (Farrugia, 1999).

Hydrogen-bond geometry (Å, º) top

Cg1, Cg2, Cg3 and Cg4 are the centroids of the C31–C36, C37–C42, C2–C7 and C23–C28 rings, respectively.

D—H···A	D—H	H···A	D···A	D—H···A
C3—H3···Cg1ⁱ	0.93	2.81	3.7152 (18)	166
C6—H6···Cg1ⁱⁱ	0.93	2.66	3.5506 (19)	160
C9—H9C···Cg2ⁱⁱⁱ	0.96	2.97	3.7170 (19)	136
C29—H29B···Cg3^iv	0.96	3.00	3.931 (2)	165
C41—H41···Cg4ⁱ	0.93	2.83	3.590 (2)	139

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

Acknowledgements

The authors are grateful to VIEP–BUAP for the supporting project CAVB-NAT-I10.

References

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