N,N'-Bis(3,4-dimethoxy-benzyl-idene)butane-1,4-diamine.

The title Schiff base compound, C(22)H(28)N(2)O(4), was synthesized by the reaction of 3,4-dimethoxy-benzaldehyde and 1,4-diamino-butane in methanol. The mol-ecule is located on a center of inversion with one half-mol-ecule in the asymmetric unit. Both C=N double bonds are in a trans configuration. Inter-molecular C-H⋯O hydrogen bonds link the mol-ecules into a three-dimensional network.

Related literature

For related structures, see: Khalaji & Ng (2008 ▶); Khalaji et al. (2007 ▶).

Experimental

Crystal data

C22H28N2O4

M = 384.5

Monoclinic,

a = 14.5770 (4) Å

b = 7.6201 (2) Å

c = 9.4456 (3) Å

β = 101.725 (2)°

V = 1027.31 (5) Å3

Z = 2

Cu Kα radiation

μ = 0.69 mm−1

T = 120 K

0.29 × 0.16 × 0.09 mm

Data collection

Oxford Diffraction Gemini diffractometer with Xcalibur goniometer, an Atlas detector and a Gemini ultra Cu source

Absorption correction: multi-scan (CrysAlis RED; Oxford Diffraction, 2009 ▶) T min = 0.765, T max = 0.935

5312 measured reflections

1594 independent reflections

1293 reflections with I > 3σ(I)

R int = 0.024

θmax = 62.3°

Refinement

R[F 2 > 2σ(F 2)] = 0.035

wR(F 2) = 0.096

S = 1.67

1594 reflections

127 parameters

H-atom parameters constrained

Δρmax = 0.13 e Å−3

Δρmin = −0.14 e Å−3

Data collection: CrysAlis CCD (Oxford Diffraction, 2009 ▶); cell refinement: CrysAlis RED (Oxford Diffraction, 2009 ▶); data reduction: CrysAlis RED; program(s) used to solve structure: SIR2002 (Burla et al., 2003 ▶); program(s) used to refine structure: JANA2006 (Petříček et al., 2006 ▶); molecular graphics: DIAMOND (Brandenburg & Putz, 2005 ▶); software used to prepare material for publication: JANA2006.

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536809025069/bt2985sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536809025069/bt2985Isup2.hkl

Additional supplementary materials: crystallographic information; 3D view; checkCIF report

C22H28N2O4	F(000) = 412
Mr = 384.5	Dx = 1.243 Mg m−3
Monoclinic, P21/c	Cu Kα radiation, λ = 1.54184 Å
Hall symbol: -P 2ybc	Cell parameters from 3320 reflections
a = 14.5770 (4) Å	θ = 3.1–62.2°
b = 7.6201 (2) Å	µ = 0.69 mm−1
c = 9.4456 (3) Å	T = 120 K
β = 101.725 (2)°	Prism, colorless
V = 1027.31 (5) Å3	0.28 × 0.16 × 0.09 mm
Z = 2

Oxford Diffraction Gemini diffractometer with Xcalibur goniometer, an Atlas detector and a Gemini ultra Cu source	1594 independent reflections
Radiation source: X-ray tube	1293 reflections with I > 3σ(I)
mirror	Rint = 0.024
Detector resolution: 20.7567 pixels mm-1	θmax = 62.3°, θmin = 6.2°
Rotation method data acquisition using ω scans	h = −15→16
Absorption correction: multi-scan (CrysAlis RED; Oxford Diffraction, 2009)	k = −6→8
Tmin = 0.765, Tmax = 0.935	l = −10→8
5312 measured reflections

Refinement on F2	56 constraints
R[F2 > 2σ(F2)] = 0.035	H-atom parameters constrained
wR(F2) = 0.096	Weighting scheme based on measured s.u.'s w = 1/[σ2(I) + 0.0016I2]
S = 1.67	(Δ/σ)max = 0.010
1594 reflections	Δρmax = 0.13 e Å−3
127 parameters	Δρmin = −0.14 e Å−3
0 restraints

Refinement. The refinement was carried out against all reflections. The conventional R-factor is always based on F. The goodness of fit as well as the weighted R-factor are based on F and F2 for refinement carried out on F and F2, respectively. The threshold expression is used only for calculating R-factors etc. and it is not relevant to the choice of reflections for refinement.The program used for refinement, Jana2006, uses the weighting scheme based on the experimental expectations, see _refine_ls_weighting_details, that does not force S to be one. Therefore the values of S are usually larger than the ones from the SHELX program.

	x	y	z	Uiso*/Ueq
O1	0.32039 (6)	−0.14609 (12)	0.79180 (10)	0.0270 (3)
O2	0.44401 (6)	0.09623 (12)	0.85186 (10)	0.0273 (3)
N1	0.09135 (9)	0.06805 (17)	0.32350 (12)	0.0300 (4)
C1	0.22426 (10)	0.16821 (19)	0.50087 (14)	0.0249 (4)
C2	0.23245 (10)	0.01522 (19)	0.58506 (14)	0.0253 (5)
C3	0.30568 (10)	−0.00345 (17)	0.70163 (14)	0.0230 (4)
C4	0.37318 (9)	0.13126 (18)	0.73672 (14)	0.0238 (4)
C5	0.36408 (10)	0.28352 (19)	0.65593 (14)	0.0267 (5)
C6	0.28914 (10)	0.30120 (19)	0.53867 (14)	0.0268 (5)
C7	0.14929 (10)	0.1882 (2)	0.37154 (14)	0.0271 (5)
C8	0.02298 (10)	0.1056 (2)	0.19086 (15)	0.0328 (5)
C9	0.03674 (10)	−0.01461 (19)	0.06882 (14)	0.0280 (5)
C10	0.25804 (11)	−0.2911 (2)	0.75602 (16)	0.0335 (5)
C11	0.50866 (10)	0.2352 (2)	0.89969 (16)	0.0334 (5)
H2	0.186873	−0.076684	0.56133	0.0303*
H5	0.40895	0.376514	0.680225	0.032*
H6	0.282503	0.407674	0.483197	0.0322*
H7	0.144082	0.298205	0.320967	0.0325*
H8a	0.02928	0.225547	0.163206	0.0393*
H8b	−0.039196	0.0907	0.208212	0.0393*
H9a	0.098065	0.003565	0.048977	0.0337*
H9b	0.034701	−0.13463	0.098931	0.0337*
H10a	0.278325	−0.386148	0.821663	0.0402*
H10b	0.195898	−0.256261	0.763371	0.0402*
H10c	0.257961	−0.328557	0.658943	0.0402*
H11a	0.55323	0.197841	0.983561	0.0401*
H11b	0.540945	0.265307	0.82402	0.0401*
H11c	0.475258	0.335902	0.923628	0.0401*

	U11	U22	U33	U12	U13	U23
O1	0.0291 (6)	0.0255 (5)	0.0232 (5)	−0.0036 (4)	−0.0026 (4)	0.0037 (4)
O2	0.0245 (5)	0.0302 (6)	0.0231 (5)	−0.0033 (4)	−0.0049 (4)	0.0017 (4)
N1	0.0301 (7)	0.0343 (7)	0.0218 (6)	0.0028 (6)	−0.0036 (5)	−0.0020 (5)
C1	0.0275 (8)	0.0271 (8)	0.0189 (7)	0.0039 (6)	0.0018 (6)	−0.0010 (6)
C2	0.0246 (7)	0.0285 (8)	0.0213 (7)	−0.0002 (6)	0.0014 (6)	−0.0043 (6)
C3	0.0264 (7)	0.0236 (8)	0.0182 (7)	0.0025 (6)	0.0024 (5)	0.0000 (6)
C4	0.0230 (7)	0.0293 (8)	0.0176 (7)	0.0017 (6)	0.0009 (6)	−0.0020 (6)
C5	0.0276 (8)	0.0278 (8)	0.0234 (7)	−0.0032 (6)	0.0021 (6)	−0.0005 (6)
C6	0.0319 (8)	0.0272 (8)	0.0208 (7)	0.0021 (6)	0.0037 (6)	0.0019 (6)
C7	0.0308 (8)	0.0284 (8)	0.0200 (7)	0.0057 (7)	0.0003 (6)	−0.0008 (6)
C8	0.0307 (8)	0.0365 (9)	0.0262 (8)	0.0043 (7)	−0.0059 (6)	−0.0004 (7)
C9	0.0252 (8)	0.0302 (8)	0.0258 (8)	−0.0001 (6)	−0.0019 (6)	0.0027 (6)
C10	0.0362 (9)	0.0277 (8)	0.0326 (8)	−0.0072 (7)	−0.0022 (7)	0.0042 (6)
C11	0.0283 (8)	0.0373 (9)	0.0299 (8)	−0.0088 (7)	−0.0052 (6)	0.0016 (7)

O1—C3	1.3706 (16)	C6—H6	0.96
O1—C10	1.4272 (18)	C7—H7	0.96
O2—C4	1.3651 (14)	C8—C9	1.517 (2)
O2—C11	1.4287 (17)	C8—H8a	0.96
N1—C7	1.2657 (19)	C8—H8b	0.96
N1—C8	1.4620 (17)	C9—C9i	1.5236 (17)
C1—C2	1.403 (2)	C9—H9a	0.96
C1—C6	1.383 (2)	C9—H9b	0.96
C1—C7	1.4722 (17)	C10—H10a	0.96
C2—C3	1.3763 (17)	C10—H10b	0.96
C2—H2	0.96	C10—H10c	0.96
C3—C4	1.4139 (19)	C11—H11a	0.96
C4—C5	1.380 (2)	C11—H11b	0.96
C5—C6	1.3951 (18)	C11—H11c	0.96
C5—H5	0.96
C3—O1—C10	117.08 (10)	N1—C8—C9	111.13 (12)
C4—O2—C11	116.78 (10)	N1—C8—H8a	109.4714
C7—N1—C8	117.04 (12)	N1—C8—H8b	109.4713
C2—C1—C6	119.20 (11)	C9—C8—H8a	109.4714
C2—C1—C7	121.32 (13)	C9—C8—H8b	109.471
C6—C1—C7	119.46 (13)	H8a—C8—H8b	107.7587
C1—C2—C3	120.15 (13)	C8—C9—C9i	112.43 (12)
C1—C2—H2	119.9235	C8—C9—H9a	109.4708
C3—C2—H2	119.9231	C8—C9—H9b	109.4709
O1—C3—C2	125.24 (12)	C9i—C9—H9a	109.4717
O1—C3—C4	114.61 (11)	C9i—C9—H9b	109.4713
C2—C3—C4	120.14 (12)	H9a—C9—H9b	106.344
O2—C4—C3	114.99 (11)	O1—C10—H10a	109.4718
O2—C4—C5	125.24 (12)	O1—C10—H10b	109.4712
C3—C4—C5	119.77 (11)	O1—C10—H10c	109.4714
C4—C5—C6	119.46 (13)	H10a—C10—H10b	109.471
C4—C5—H5	120.2676	H10a—C10—H10c	109.4712
C6—C5—H5	120.2684	H10b—C10—H10c	109.4707
C1—C6—C5	121.22 (13)	O2—C11—H11a	109.4712
C1—C6—H6	119.3878	O2—C11—H11b	109.4717
C5—C6—H6	119.3886	O2—C11—H11c	109.4713
N1—C7—C1	123.46 (13)	H11a—C11—H11b	109.4716
N1—C7—H7	118.272	H11a—C11—H11c	109.4708
C1—C7—H7	118.2721	H11b—C11—H11c	109.4708

D—H···A	D—H	H···A	D···A	D—H···A
C11—H11A···O1ii	0.96	2.54	3.4945 (17)	171
C11—H11B···O1iii	0.96	2.58	3.4830 (17)	158

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C11—H11A⋯O1i	0.96	2.54	3.4945 (17)	171
C11—H11B⋯O1ii	0.96	2.58	3.4830 (17)	158

Symmetry codes: (i) ; (ii) .