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The title compound, C22H28N2O4, is a potential multidentate azomethine ligand. The asymmetric unit contains two half-molecules, each molecule lying on a centre of symmetry. The mol­ecules are linked into sheets and a three-dimensional network by C—H...O hydrogen bonds and van der Waals forces.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536806053062/at2182sup1.cif
Contains datablocks I, global

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536806053062/at2182Isup2.hkl
Contains datablock I

CCDC reference: 633591

Key indicators

  • Single-crystal X-ray study
  • T = 293 K
  • Mean [sigma](C-C) = 0.009 Å
  • R factor = 0.073
  • wR factor = 0.277
  • Data-to-parameter ratio = 14.3

checkCIF/PLATON results

No syntax errors found



Alert level B PLAT026_ALERT_3_B Ratio Observed / Unique Reflections too Low .... 34 Perc.
Alert level C RFACR01_ALERT_3_C The value of the weighted R factor is > 0.25 Weighted R factor given 0.277 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 PLAT066_ALERT_1_C Predicted and Reported Transmissions Identical . ? PLAT084_ALERT_2_C High R2 Value .................................. 0.28 PLAT241_ALERT_2_C Check High Ueq as Compared to Neighbors for C9 PLAT241_ALERT_2_C Check High Ueq as Compared to Neighbors for C20 PLAT340_ALERT_3_C Low Bond Precision on C-C bonds (x 1000) Ang ... 9 PLAT360_ALERT_2_C Short C(sp3)-C(sp3) Bond C9 - C10 ... 1.40 Ang. PLAT360_ALERT_2_C Short C(sp3)-C(sp3) Bond C11 - C11_a ... 1.42 Ang. PLAT480_ALERT_4_C Long H...A H-Bond Reported H8A .. O1 .. 2.67 Ang.
Alert level G PLAT199_ALERT_1_G Check the Reported _cell_measurement_temperature 293 K PLAT200_ALERT_1_G Check the Reported _diffrn_ambient_temperature . 293 K
0 ALERT level A = In general: serious problem 1 ALERT level B = Potentially serious problem 11 ALERT level C = Check and explain 2 ALERT level G = General alerts; check 3 ALERT type 1 CIF construction/syntax error, inconsistent or missing data 5 ALERT type 2 Indicator that the structure model may be wrong or deficient 5 ALERT type 3 Indicator that the structure quality may be low 1 ALERT type 4 Improvement, methodology, query or suggestion 0 ALERT type 5 Informative message, check

Computing details top

Data collection: SMART (Siemens, 1996); cell refinement: SMART; data reduction: SAINT (Siemens, 1996); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997a); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997a); molecular graphics: SHELXTL (Sheldrick, 1997b); software used to prepare material for publication: SHELXTL.

6,6'-Dimethoxy-2,2'-(hexane-1,6-diyldinitrilodimethylidyne)diphenol top
Crystal data top
C22H28N2O4F(000) = 824
Mr = 384.46Dx = 1.240 Mg m3
Monoclinic, P21/cMo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybcCell parameters from 899 reflections
a = 21.834 (11) Åθ = 2.6–19.8°
b = 8.420 (4) ŵ = 0.09 mm1
c = 11.203 (6) ÅT = 293 K
β = 91.778 (9)°Plate, yellow
V = 2058.6 (19) Å30.52 × 0.48 × 0.15 mm
Z = 4
Data collection top
Bruker SMART CCD area-detector
diffractometer
3621 independent reflections
Radiation source: fine-focus sealed tube1223 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.102
φ and ω scansθmax = 25.0°, θmin = 1.9°
Absorption correction: multi-scan
(SADABS; Sheldrick, 1996)
h = 2525
Tmin = 0.957, Tmax = 0.987k = 109
10347 measured reflectionsl = 136
Refinement top
Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.073Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.277H-atom parameters constrained
S = 1.02 w = 1/[σ2(Fo2) + (0.0391P)2 + 1.1443P]
where P = (Fo2 + 2Fc2)/3
3621 reflections(Δ/σ)max < 0.001
253 parametersΔρmax = 0.20 e Å3
0 restraintsΔρmin = 0.24 e Å3
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
xyzUiso*/Ueq
N10.4265 (3)0.0897 (7)0.8446 (5)0.0832 (18)
N20.0901 (2)0.3990 (6)0.6828 (4)0.0604 (14)
O10.43011 (18)0.0516 (5)1.0496 (4)0.0779 (14)
H10.44200.02330.98420.117*
O20.37742 (19)0.1263 (5)1.2498 (4)0.0819 (14)
O30.15944 (16)0.3791 (4)0.8715 (3)0.0656 (12)
H30.13900.34800.81350.098*
O40.2200 (2)0.5193 (5)1.0454 (4)0.0882 (15)
C10.3737 (4)0.1425 (7)0.8714 (6)0.075 (2)
H1A0.35290.20820.81720.090*
C20.3451 (3)0.1044 (7)0.9821 (6)0.0608 (17)
C30.3757 (3)0.0073 (7)1.0666 (6)0.0588 (16)
C40.3457 (3)0.0280 (7)1.1736 (6)0.0593 (16)
C50.2890 (3)0.0350 (8)1.1948 (6)0.0699 (19)
H50.26940.01111.26510.084*
C60.2611 (3)0.1356 (8)1.1098 (8)0.083 (2)
H60.22370.18201.12640.100*
C70.2868 (3)0.1672 (7)1.0050 (7)0.077 (2)
H70.26630.22980.94820.093*
C80.3501 (3)0.1648 (9)1.3594 (6)0.100 (2)
H8A0.37640.23571.40420.150*
H8B0.31130.21531.34350.150*
H8C0.34410.06951.40460.150*
C90.4527 (4)0.1385 (10)0.7304 (7)0.114 (3)
H9A0.42660.21940.69380.137*
H9B0.49270.18530.74620.137*
C100.4586 (4)0.0125 (10)0.6498 (7)0.112 (3)
H10A0.41880.03620.63620.134*
H10B0.48550.06690.68580.134*
C110.4838 (4)0.0605 (8)0.5297 (7)0.109 (3)
H11A0.44990.09510.47800.131*
H11B0.51090.15070.54200.131*
C120.0887 (2)0.5478 (8)0.6962 (5)0.0574 (16)
H120.06590.60910.64200.069*
C130.1218 (2)0.6251 (6)0.7938 (5)0.0484 (14)
C140.1562 (2)0.5402 (7)0.8781 (5)0.0500 (15)
C150.1882 (3)0.6160 (7)0.9706 (5)0.0571 (16)
C160.1864 (3)0.7786 (8)0.9770 (6)0.0679 (19)
H160.20830.83071.03780.082*
C170.1526 (3)0.8655 (8)0.8943 (6)0.0746 (19)
H170.15160.97570.89990.089*
C180.1203 (3)0.7906 (8)0.8035 (6)0.0697 (19)
H180.09740.85010.74820.084*
C190.2583 (3)0.5889 (9)1.1358 (6)0.096 (2)
H19A0.27780.50671.18260.144*
H19B0.23400.65411.18640.144*
H19C0.28900.65301.09960.144*
C200.0555 (3)0.3314 (7)0.5804 (5)0.077 (2)
H20A0.07820.34820.50840.092*
H20B0.01660.38610.57080.092*
C210.0443 (2)0.1582 (6)0.5958 (5)0.0557 (16)
H21A0.02450.14100.67110.067*
H21B0.08330.10290.59950.067*
C220.0047 (2)0.0892 (6)0.4958 (5)0.0554 (16)
H22A0.02340.11310.42040.066*
H22B0.03500.14090.49550.066*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
N10.112 (5)0.083 (4)0.056 (4)0.001 (4)0.014 (4)0.003 (3)
N20.071 (3)0.053 (3)0.056 (3)0.007 (3)0.009 (3)0.001 (3)
O10.069 (3)0.101 (3)0.065 (3)0.025 (2)0.015 (2)0.020 (2)
O20.083 (3)0.103 (4)0.060 (3)0.008 (3)0.010 (3)0.013 (3)
O30.074 (3)0.049 (3)0.073 (3)0.0012 (19)0.015 (2)0.001 (2)
O40.098 (3)0.074 (3)0.090 (3)0.008 (3)0.037 (3)0.015 (3)
C10.104 (6)0.058 (4)0.063 (5)0.002 (4)0.014 (5)0.008 (4)
C20.072 (4)0.049 (4)0.060 (5)0.002 (3)0.013 (4)0.000 (3)
C30.057 (4)0.062 (4)0.058 (4)0.002 (3)0.002 (4)0.009 (4)
C40.059 (4)0.061 (4)0.059 (4)0.000 (3)0.000 (4)0.002 (4)
C50.061 (4)0.073 (5)0.076 (5)0.012 (4)0.013 (4)0.018 (4)
C60.067 (4)0.071 (5)0.111 (7)0.007 (4)0.006 (5)0.021 (5)
C70.075 (5)0.060 (4)0.096 (6)0.014 (4)0.013 (5)0.004 (4)
C80.099 (5)0.140 (7)0.062 (5)0.019 (5)0.011 (5)0.023 (5)
C90.168 (8)0.101 (7)0.074 (6)0.021 (6)0.023 (6)0.023 (5)
C100.141 (7)0.111 (7)0.087 (6)0.006 (5)0.060 (6)0.006 (5)
C110.121 (7)0.099 (7)0.110 (7)0.011 (5)0.040 (6)0.008 (5)
C120.056 (4)0.063 (4)0.053 (4)0.004 (3)0.001 (3)0.008 (4)
C130.053 (3)0.043 (4)0.049 (4)0.002 (3)0.008 (3)0.005 (3)
C140.055 (3)0.041 (4)0.055 (4)0.002 (3)0.007 (3)0.007 (3)
C150.058 (4)0.055 (4)0.057 (4)0.004 (3)0.003 (3)0.011 (4)
C160.068 (4)0.058 (4)0.078 (5)0.004 (3)0.007 (4)0.026 (4)
C170.099 (5)0.050 (4)0.075 (5)0.006 (4)0.013 (5)0.007 (4)
C180.081 (4)0.061 (5)0.067 (5)0.014 (4)0.008 (4)0.008 (4)
C190.088 (5)0.120 (6)0.077 (5)0.006 (4)0.031 (5)0.018 (5)
C200.100 (5)0.065 (5)0.064 (4)0.015 (4)0.023 (4)0.003 (4)
C210.062 (4)0.055 (4)0.050 (4)0.002 (3)0.002 (3)0.002 (3)
C220.059 (3)0.059 (4)0.048 (4)0.006 (3)0.000 (3)0.002 (3)
Geometric parameters (Å, º) top
N1—C11.280 (7)C10—C111.523 (9)
N1—C91.476 (8)C10—H10A0.9700
N2—C121.262 (6)C10—H10B0.9700
N2—C201.469 (7)C11—C11i1.418 (13)
O1—C31.308 (6)C11—H11A0.9700
O1—H10.8200C11—H11B0.9700
O2—C41.363 (7)C12—C131.446 (7)
O2—C81.419 (7)C12—H120.9300
O3—C141.361 (6)C13—C141.387 (7)
O3—H30.8200C13—C181.397 (7)
O4—C151.346 (7)C14—C151.387 (7)
O4—C191.420 (7)C15—C161.372 (7)
C1—C21.441 (8)C16—C171.378 (8)
C1—H1A0.9300C16—H160.9300
C2—C31.403 (8)C17—C181.373 (8)
C2—C71.410 (8)C17—H170.9300
C3—C41.415 (8)C18—H180.9300
C4—C51.373 (8)C19—H19A0.9600
C5—C61.400 (9)C19—H19B0.9600
C5—H50.9300C19—H19C0.9600
C6—C71.343 (9)C20—C211.490 (7)
C6—H60.9300C20—H20A0.9700
C7—H70.9300C20—H20B0.9700
C8—H8A0.9600C21—C221.510 (7)
C8—H8B0.9600C21—H21A0.9700
C8—H8C0.9600C21—H21B0.9700
C9—C101.402 (9)C22—C22ii1.519 (9)
C9—H9A0.9700C22—H22A0.9700
C9—H9B0.9700C22—H22B0.9700
C1—N1—C9118.8 (7)C11i—C11—H11B108.5
C12—N2—C20117.7 (5)C10—C11—H11B108.5
C3—O1—H1109.5H11A—C11—H11B107.5
C4—O2—C8117.5 (5)N2—C12—C13121.6 (6)
C14—O3—H3109.5N2—C12—H12119.2
C15—O4—C19118.4 (5)C13—C12—H12119.2
N1—C1—C2122.8 (7)C14—C13—C18118.3 (6)
N1—C1—H1A118.6C14—C13—C12122.0 (5)
C2—C1—H1A118.6C18—C13—C12119.7 (6)
C3—C2—C7120.5 (6)O3—C14—C13120.4 (5)
C3—C2—C1120.0 (6)O3—C14—C15118.2 (5)
C7—C2—C1119.4 (7)C13—C14—C15121.4 (5)
O1—C3—C2122.5 (6)O4—C15—C16125.9 (6)
O1—C3—C4119.4 (6)O4—C15—C14115.2 (5)
C2—C3—C4118.1 (6)C16—C15—C14119.0 (6)
O2—C4—C5124.7 (6)C15—C16—C17120.7 (6)
O2—C4—C3114.7 (5)C15—C16—H16119.7
C5—C4—C3120.6 (7)C17—C16—H16119.7
C4—C5—C6119.4 (7)C18—C17—C16120.4 (6)
C4—C5—H5120.3C18—C17—H17119.8
C6—C5—H5120.3C16—C17—H17119.8
C7—C6—C5122.0 (6)C17—C18—C13120.2 (6)
C7—C6—H6119.0C17—C18—H18119.9
C5—C6—H6119.0C13—C18—H18119.9
C6—C7—C2119.2 (7)O4—C19—H19A109.5
C6—C7—H7120.4O4—C19—H19B109.5
C2—C7—H7120.4H19A—C19—H19B109.5
O2—C8—H8A109.5O4—C19—H19C109.5
O2—C8—H8B109.5H19A—C19—H19C109.5
H8A—C8—H8B109.5H19B—C19—H19C109.5
O2—C8—H8C109.5N2—C20—C21111.8 (5)
H8A—C8—H8C109.5N2—C20—H20A109.3
H8B—C8—H8C109.5C21—C20—H20A109.3
C10—C9—N1113.2 (6)N2—C20—H20B109.3
C10—C9—H9A108.9C21—C20—H20B109.3
N1—C9—H9A108.9H20A—C20—H20B107.9
C10—C9—H9B108.9C20—C21—C22112.5 (5)
N1—C9—H9B108.9C20—C21—H21A109.1
H9A—C9—H9B107.7C22—C21—H21A109.1
C9—C10—C11114.3 (7)C20—C21—H21B109.1
C9—C10—H10A108.7C22—C21—H21B109.1
C11—C10—H10A108.7H21A—C21—H21B107.8
C9—C10—H10B108.7C21—C22—C22ii114.3 (6)
C11—C10—H10B108.7C21—C22—H22A108.7
H10A—C10—H10B107.6C22ii—C22—H22A108.7
C11i—C11—C10115.0 (9)C21—C22—H22B108.7
C11i—C11—H11A108.5C22ii—C22—H22B108.7
C10—C11—H11A108.5H22A—C22—H22B107.6
C9—N1—C1—C2178.5 (6)C20—N2—C12—C13179.4 (5)
N1—C1—C2—C30.9 (9)N2—C12—C13—C140.5 (8)
N1—C1—C2—C7179.9 (6)N2—C12—C13—C18178.3 (5)
C7—C2—C3—O1179.1 (5)C18—C13—C14—O3179.4 (4)
C1—C2—C3—O10.1 (9)C12—C13—C14—O30.6 (7)
C7—C2—C3—C41.3 (8)C18—C13—C14—C150.5 (8)
C1—C2—C3—C4179.5 (5)C12—C13—C14—C15179.3 (5)
C8—O2—C4—C50.6 (9)C19—O4—C15—C163.8 (9)
C8—O2—C4—C3179.3 (5)C19—O4—C15—C14174.4 (5)
O1—C3—C4—O21.3 (8)O3—C14—C15—O40.3 (7)
C2—C3—C4—O2178.3 (5)C13—C14—C15—O4179.6 (5)
O1—C3—C4—C5178.6 (5)O3—C14—C15—C16178.7 (5)
C2—C3—C4—C51.8 (8)C13—C14—C15—C161.2 (8)
O2—C4—C5—C6179.6 (6)O4—C15—C16—C17179.3 (6)
C3—C4—C5—C60.3 (9)C14—C15—C16—C171.2 (8)
C4—C5—C6—C73.1 (10)C15—C16—C17—C180.4 (9)
C5—C6—C7—C23.5 (10)C16—C17—C18—C130.3 (9)
C3—C2—C7—C61.3 (9)C14—C13—C18—C170.3 (8)
C1—C2—C7—C6177.9 (6)C12—C13—C18—C17178.6 (5)
C1—N1—C9—C10113.9 (9)C12—N2—C20—C21161.7 (5)
N1—C9—C10—C11178.3 (7)N2—C20—C21—C22175.7 (5)
C9—C10—C11—C11i152.1 (10)C20—C21—C22—C22ii176.5 (6)
Symmetry codes: (i) x+1, y, z+1; (ii) x, y, z+1.
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
C8—H8A···O1iii0.962.673.616 (8)169
Symmetry code: (iii) x, y1/2, z+1/2.
 

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