N,N'-Bis(2,3-dimethoxy-benzyl-idene)propane-1,3-diamine.

The title compound, C(21)H(26)N(2)O(4), adopts an E configuration with respect to the azomethine C=N bonds. The dihedral angle between the two rings is 8.16 (8)°. The crystal structure is stabilized by weak inter-molecular C-H⋯O inter-actions.

Related literature

For the chemistry of Schiff base derivatives, see: Morshedi et al. (2009a ▶,b ▶); Dehno Khalaji et al. (2009 ▶); Khalaji et al. (2007 ▶); Wang (2008 ▶); Fun et al. (2008 ▶). For their applications, see: Ardizzoia et al. (2009 ▶); Gao et al. (2003 ▶). For the extinction correction, see: Becker & Coppens (1974 ▶).

Experimental

Crystal data

C21H26N2O4

M = 370.4

Orthorhombic,

a = 15.3079 (3) Å

b = 9.2915 (2) Å

c = 13.8059 (3) Å

V = 1963.66 (7) Å3

Z = 4

Cu Kα radiation

μ = 0.71 mm−1

T = 120 K

0.51 × 0.31 × 0.20 mm

Data collection

Oxford Diffraction Xcalibur diffractometer with an Atlas (Gemini ultra Cu) detector

Absorption correction: multi-scan (CrysAlis Pro; Oxford Diffraction, 2009 ▶) T min = 0.628, T max = 0.871

26538 measured reflections

1623 independent reflections

1616 reflections with I > 3σ(I)

R int = 0.021

θmax = 62.4°

Refinement

R[F 2 > 2σ(F 2)] = 0.025

wR(F 2) = 0.077

S = 1.97

1623 reflections

244 parameters

H-atom parameters constrained

Δρmax = 0.10 e Å−3

Δρmin = −0.09 e Å−3

Data collection: CrysAlis Pro (Oxford Diffraction, 2009 ▶); cell refinement: CrysAlis Pro; data reduction: CrysAlis Pro; program(s) used to solve structure: SIR2002 (Burla et al., 2003 ▶); program(s) used to refine structure: JANA2006 (Petříček et al., 2007 ▶); molecular graphics: DIAMOND (Brandenburg & Putz, 2005 ▶); software used to prepare material for publication: JANA2006.

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536809031651/bt5030sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536809031651/bt5030Isup2.hkl

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

C21H26N2O4	F(000) = 792
Mr = 370.4	Dx = 1.253 Mg m−3
Orthorhombic, Pna21	Cu Kα radiation, λ = 1.54184 Å
Hall symbol: P 2c -2n	Cell parameters from 24214 reflections
a = 15.3079 (3) Å	θ = 3.2–62.3°
b = 9.2915 (2) Å	µ = 0.71 mm−1
c = 13.8059 (3) Å	T = 120 K
V = 1963.66 (7) Å3	Irregular shape, colorless
Z = 4	0.51 × 0.31 × 0.20 mm

Oxford Diffraction Xcalibur diffractometer with an Atlas (Gemini ultra Cu) detector	1623 independent reflections
Radiation source: X-ray tube	1616 reflections with I > 3σ(I)
mirror	Rint = 0.021
Detector resolution: 20.7567 pixels mm-1	θmax = 62.4°, θmin = 5.6°
Rotation method data acquisition using ω scans	h = −17→17
Absorption correction: multi-scan (CrysAlis PRO; Oxford Diffraction, 2009)	k = −10→10
Tmin = 0.628, Tmax = 0.871	l = −15→15
26538 measured reflections

Refinement on F2	H-atom parameters constrained
R[F2 > 2σ(F2)] = 0.025	Weighting scheme based on measured s.u.'s w = 1/[σ2(I) + 0.0016I2]
wR(F2) = 0.077	(Δ/σ)max = 0.038
S = 1.97	Δρmax = 0.10 e Å−3
1623 reflections	Δρmin = −0.09 e Å−3
244 parameters	Extinction correction: B–C type 1 Lorentzian isotropic (Becker & Coppens, 1974)
0 restraints	Extinction coefficient: 2800 (1000)
105 constraints

Experimental. CrysAlisPro (Oxford Diffraction, 2009) Version 1.171.33.34d (release 27-02-2009 CrysAlis171 .NET) Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm.

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	0.26797 (8)	0.00499 (13)	0.18586 (12)	0.0306 (4)
O2	0.18047 (7)	−0.18392 (11)	0.07546 (13)	0.0282 (3)
O3	0.46602 (7)	0.01788 (12)	0.27381 (11)	0.0315 (4)
O4	0.57090 (7)	−0.12117 (13)	0.40069 (13)	0.0348 (4)
N1	0.22853 (8)	0.43567 (14)	0.17846 (14)	0.0279 (4)
N2	0.46937 (8)	0.45543 (14)	0.24531 (14)	0.0281 (4)
C1	0.18698 (9)	0.20195 (17)	0.11887 (15)	0.0239 (4)
C2	0.20316 (10)	0.05443 (16)	0.12523 (15)	0.0239 (4)
C3	0.16066 (9)	−0.04171 (17)	0.06289 (16)	0.0246 (4)
C4	0.10498 (10)	0.01093 (17)	−0.00881 (15)	0.0274 (5)
C5	0.09133 (10)	0.15967 (17)	−0.01601 (15)	0.0292 (5)
C6	0.13056 (11)	0.25368 (17)	0.04693 (16)	0.0272 (5)
C7	0.23004 (10)	0.30040 (17)	0.18825 (14)	0.0246 (4)
C8	0.27152 (10)	0.52016 (17)	0.25365 (14)	0.0263 (5)
C9	0.34446 (10)	0.61189 (16)	0.21099 (14)	0.0262 (5)
C10	0.41895 (11)	0.52360 (17)	0.16833 (15)	0.0277 (5)
C11	0.47382 (10)	0.31972 (17)	0.24671 (15)	0.0253 (5)
C12	0.52555 (9)	0.24424 (17)	0.32177 (14)	0.0244 (4)
C13	0.52359 (10)	0.09464 (17)	0.32989 (15)	0.0249 (4)
C14	0.57636 (10)	0.02498 (19)	0.39893 (16)	0.0275 (5)
C15	0.62910 (10)	0.10661 (19)	0.46004 (15)	0.0301 (5)
C16	0.62956 (11)	0.25595 (19)	0.45242 (15)	0.0303 (5)
C17	0.57829 (10)	0.32443 (18)	0.38485 (15)	0.0272 (5)
C18	0.23861 (13)	−0.0640 (2)	0.27226 (15)	0.0402 (6)
C19	0.14018 (12)	−0.28468 (19)	0.01141 (16)	0.0327 (5)
C20	0.50416 (12)	−0.0730 (2)	0.20153 (18)	0.0396 (6)
C21	0.62707 (12)	−0.1948 (2)	0.46665 (17)	0.0400 (6)
H4	0.076366	−0.053919	−0.052675	0.0329*
H5	0.053814	0.196398	−0.065946	0.035*
H6	0.119366	0.355051	0.041722	0.0327*
H7	0.260269	0.26004	0.242784	0.0295*
H8a	0.295303	0.456715	0.301782	0.0315*
H8b	0.229431	0.581308	0.284681	0.0315*
H9a	0.32086	0.674064	0.162003	0.0314*
H9b	0.366972	0.675138	0.259983	0.0314*
H10a	0.395548	0.450955	0.126235	0.0333*
H10b	0.456428	0.58522	0.131065	0.0333*
H11	0.443276	0.264808	0.198515	0.0303*
H15	0.66515	0.059858	0.507446	0.0361*
H16	0.666035	0.31172	0.494737	0.0364*
H17	0.5786	0.427575	0.380869	0.0327*
H18a	0.288071	−0.09841	0.308189	0.0482*
H18b	0.206536	0.003592	0.311013	0.0482*
H18c	0.201483	−0.14353	0.255709	0.0482*
H19a	0.156576	−0.380645	0.029678	0.0393*
H19b	0.077848	−0.274903	0.015211	0.0393*
H19c	0.159047	−0.266242	−0.053739	0.0393*
H20a	0.4592	−0.108672	0.159426	0.0475*
H20b	0.545747	−0.018776	0.164399	0.0475*
H20c	0.533122	−0.15241	0.23229	0.0475*
H21a	0.615974	−0.296407	0.463211	0.0479*
H21b	0.686855	−0.176274	0.449786	0.0479*
H21c	0.616154	−0.16141	0.531323	0.0479*

	U11	U22	U33	U12	U13	U23
O1	0.0289 (6)	0.0321 (7)	0.0309 (6)	0.0034 (4)	−0.0083 (5)	0.0007 (5)
O2	0.0280 (6)	0.0220 (6)	0.0346 (6)	−0.0006 (4)	−0.0038 (5)	−0.0025 (5)
O3	0.0245 (6)	0.0338 (6)	0.0362 (7)	−0.0033 (4)	−0.0073 (5)	−0.0013 (5)
O4	0.0298 (6)	0.0339 (6)	0.0405 (7)	−0.0035 (4)	−0.0091 (5)	0.0143 (6)
N1	0.0261 (7)	0.0265 (7)	0.0310 (8)	0.0016 (5)	−0.0001 (6)	−0.0017 (6)
N2	0.0267 (7)	0.0287 (7)	0.0288 (7)	0.0025 (5)	0.0028 (6)	−0.0020 (6)
C1	0.0185 (7)	0.0264 (8)	0.0268 (8)	0.0012 (6)	0.0048 (6)	−0.0005 (7)
C2	0.0185 (7)	0.0281 (8)	0.0250 (8)	0.0017 (6)	0.0011 (6)	−0.0002 (6)
C3	0.0194 (7)	0.0245 (8)	0.0298 (8)	−0.0010 (5)	0.0052 (7)	−0.0003 (7)
C4	0.0179 (7)	0.0347 (9)	0.0297 (9)	−0.0020 (6)	0.0000 (7)	−0.0032 (7)
C5	0.0225 (8)	0.0348 (8)	0.0303 (10)	0.0045 (6)	−0.0027 (7)	0.0020 (7)
C6	0.0237 (8)	0.0259 (8)	0.0322 (8)	0.0035 (6)	0.0025 (6)	0.0011 (7)
C7	0.0219 (7)	0.0269 (8)	0.0250 (8)	0.0005 (6)	0.0021 (6)	−0.0006 (6)
C8	0.0286 (9)	0.0236 (7)	0.0266 (8)	0.0038 (6)	0.0008 (7)	−0.0028 (7)
C9	0.0308 (8)	0.0219 (8)	0.0258 (8)	0.0023 (6)	0.0002 (6)	−0.0004 (6)
C10	0.0306 (9)	0.0268 (8)	0.0257 (8)	0.0014 (6)	0.0025 (7)	0.0002 (7)
C11	0.0214 (8)	0.0302 (8)	0.0243 (8)	0.0007 (5)	0.0019 (6)	−0.0039 (7)
C12	0.0184 (7)	0.0313 (8)	0.0236 (8)	0.0013 (5)	0.0046 (6)	−0.0018 (7)
C13	0.0181 (7)	0.0327 (8)	0.0241 (8)	−0.0017 (6)	0.0010 (6)	−0.0002 (7)
C14	0.0213 (7)	0.0355 (8)	0.0256 (8)	−0.0001 (6)	0.0033 (6)	0.0032 (7)
C15	0.0198 (7)	0.0461 (10)	0.0243 (8)	0.0018 (7)	−0.0018 (6)	0.0025 (7)
C16	0.0229 (8)	0.0417 (9)	0.0264 (9)	0.0008 (6)	0.0011 (6)	−0.0086 (8)
C17	0.0195 (8)	0.0334 (9)	0.0289 (9)	0.0016 (6)	0.0038 (6)	−0.0073 (7)
C18	0.0560 (12)	0.0369 (10)	0.0277 (9)	0.0151 (8)	0.0010 (8)	0.0018 (7)
C19	0.0338 (9)	0.0256 (8)	0.0388 (9)	−0.0044 (7)	−0.0058 (7)	−0.0029 (7)
C20	0.0442 (10)	0.0393 (9)	0.0352 (10)	−0.0108 (8)	−0.0042 (8)	−0.0069 (8)
C21	0.0356 (10)	0.0442 (10)	0.0401 (10)	0.0030 (7)	−0.0057 (8)	0.0177 (9)

O1—C2	1.377 (2)	C9—H9a	0.96
O1—C18	1.427 (2)	C9—H9b	0.96
O2—C3	1.3668 (18)	C10—H10a	0.96
O2—C19	1.428 (2)	C10—H10b	0.96
O3—C13	1.373 (2)	C11—C12	1.481 (3)
O3—C20	1.432 (3)	C11—H11	0.96
O4—C14	1.361 (2)	C12—C13	1.395 (2)
O4—C21	1.427 (3)	C12—C17	1.402 (2)
N1—C7	1.264 (2)	C13—C14	1.407 (3)
N1—C8	1.458 (2)	C14—C15	1.392 (3)
N2—C10	1.458 (2)	C15—C16	1.392 (2)
N2—C11	1.263 (2)	C15—H15	0.96
C1—C2	1.396 (2)	C16—C17	1.375 (3)
C1—C6	1.401 (3)	C16—H16	0.96
C1—C7	1.479 (2)	C17—H17	0.96
C2—C3	1.401 (2)	C18—H18a	0.96
C3—C4	1.395 (3)	C18—H18b	0.96
C4—C5	1.401 (2)	C18—H18c	0.96
C4—H4	0.96	C19—H19a	0.96
C5—C6	1.371 (3)	C19—H19b	0.96
C5—H5	0.96	C19—H19c	0.96
C6—H6	0.96	C20—H20a	0.96
C7—H7	0.96	C20—H20b	0.96
C8—C9	1.523 (2)	C20—H20c	0.96
C8—H8a	0.96	C21—H21a	0.96
C8—H8b	0.96	C21—H21b	0.96
C9—C10	1.523 (2)	C21—H21c	0.96
C2—O1—C18	115.54 (13)	N2—C11—C12	120.82 (17)
C3—O2—C19	117.35 (15)	N2—C11—H11	119.5897
C13—O3—C20	115.95 (13)	C12—C11—H11	119.5889
C14—O4—C21	116.94 (15)	C11—C12—C13	121.11 (15)
C7—N1—C8	116.79 (16)	C11—C12—C17	119.41 (14)
C10—N2—C11	118.25 (16)	C13—C12—C17	119.48 (16)
C2—C1—C6	119.40 (16)	O3—C13—C12	119.09 (15)
C2—C1—C7	119.17 (16)	O3—C13—C14	120.77 (15)
C6—C1—C7	121.43 (14)	C12—C13—C14	120.03 (16)
O1—C2—C1	119.59 (15)	O4—C14—C13	115.84 (16)
O1—C2—C3	119.70 (13)	O4—C14—C15	124.64 (17)
C1—C2—C3	120.35 (16)	C13—C14—C15	119.52 (16)
O2—C3—C2	115.82 (16)	C14—C15—C16	120.02 (17)
O2—C3—C4	124.38 (16)	C14—C15—H15	119.9905
C2—C3—C4	119.75 (14)	C16—C15—H15	119.9904
C3—C4—C5	119.16 (16)	C15—C16—C17	120.65 (17)
C3—C4—H4	120.42	C15—C16—H16	119.6771
C5—C4—H4	120.4205	C17—C16—H16	119.6769
C4—C5—C6	121.22 (17)	C12—C17—C16	120.28 (15)
C4—C5—H5	119.3896	C12—C17—H17	119.8593
C6—C5—H5	119.3903	C16—C17—H17	119.8611
C1—C6—C5	120.05 (15)	O1—C18—H18a	109.4709
C1—C6—H6	119.9753	O1—C18—H18b	109.4711
C5—C6—H6	119.9765	O1—C18—H18c	109.4709
N1—C7—C1	122.50 (17)	H18a—C18—H18b	109.4714
N1—C7—H7	118.7511	H18a—C18—H18c	109.4717
C1—C7—H7	118.7506	H18b—C18—H18c	109.4712
N1—C8—C9	110.91 (16)	O2—C19—H19a	109.4712
N1—C8—H8a	109.4708	O2—C19—H19b	109.4713
N1—C8—H8b	109.4707	O2—C19—H19c	109.4707
C9—C8—H8a	109.4715	H19a—C19—H19b	109.4714
C9—C8—H8b	109.4712	H19a—C19—H19c	109.4716
H8a—C8—H8b	107.9975	H19b—C19—H19c	109.4711
C8—C9—C10	113.38 (13)	O3—C20—H20a	109.4712
C8—C9—H9a	109.4711	O3—C20—H20b	109.4716
C8—C9—H9b	109.471	O3—C20—H20c	109.4718
C10—C9—H9a	109.4708	H20a—C20—H20b	109.471
C10—C9—H9b	109.4724	H20a—C20—H20c	109.4707
H9a—C9—H9b	105.2553	H20b—C20—H20c	109.4711
N2—C10—C9	110.39 (16)	O4—C21—H21a	109.4718
N2—C10—H10a	109.4708	O4—C21—H21b	109.4707
N2—C10—H10b	109.4703	O4—C21—H21c	109.4713
C9—C10—H10a	109.472	H21a—C21—H21b	109.4709
C9—C10—H10b	109.4717	H21a—C21—H21c	109.4715
H10a—C10—H10b	108.5415	H21b—C21—H21c	109.4711

D—H···A	D—H	H···A	D···A	D—H···A
C5—H5···O4i	0.96	2.59	3.411 (2)	143

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C5—H5⋯O4i	0.96	2.59	3.411 (2)	143

Symmetry code: (i) .