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The title compound, C22H24N2O4, crystallizes with an inversion centre at the mid-point of the central benzene ring. Mol­ecules are linked into sheets by N—H...O and O—H...N hydrogen bonds, leading to fused R22(4) rings, which form sheets parallel to the (010) plane.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536806049208/at2160sup1.cif
Contains datablocks I, global

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536806049208/at2160Isup2.hkl
Contains datablock I

CCDC reference: 633583

Key indicators

  • Single-crystal X-ray study
  • T = 298 K
  • Mean [sigma](C-C) = 0.007 Å
  • R factor = 0.059
  • wR factor = 0.201
  • Data-to-parameter ratio = 13.4

checkCIF/PLATON results

No syntax errors found




Alert level B PLAT417_ALERT_2_B Short Inter D-H..H-D H1 .. H1A .. 1.38 Ang.
Alert level C PLAT026_ALERT_3_C Ratio Observed / Unique Reflections too Low .... 44 Perc. PLAT066_ALERT_1_C Predicted and Reported Transmissions Identical . ? PLAT340_ALERT_3_C Low Bond Precision on C-C bonds (x 1000) Ang ... 7
0 ALERT level A = In general: serious problem 1 ALERT level B = Potentially serious problem 3 ALERT level C = Check and explain 0 ALERT level G = General alerts; check 1 ALERT type 1 CIF construction/syntax error, inconsistent or missing data 1 ALERT type 2 Indicator that the structure model may be wrong or deficient 2 ALERT type 3 Indicator that the structure quality may be low 0 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.

N,N'-(2-Hydroxy-3-methoxybenzyl)benzene-1,4-diamine top
Crystal data top
C22H24N2O4F(000) = 808
Mr = 380.43Dx = 1.293 Mg m3
Orthorhombic, PccnMo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ab 2acCell parameters from 898 reflections
a = 11.308 (2) Åθ = 3.6–19.4°
b = 16.736 (3) ŵ = 0.09 mm1
c = 10.325 (2) ÅT = 298 K
V = 1954.0 (6) Å3Block, yellow
Z = 40.19 × 0.18 × 0.15 mm
Data collection top
Bruker SMART CCD area-detector
diffractometer
1702 independent reflections
Radiation source: fine-focus sealed tube753 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.094
φ and ω scansθmax = 25.0°, θmin = 2.2°
Absorption correction: multi-scan
(SADABS; Sheldrick, 1996)
h = 139
Tmin = 0.983, Tmax = 0.987k = 1919
9222 measured reflectionsl = 1211
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)] = 0.059Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.201H-atom parameters constrained
S = 1.03 w = 1/[σ2(Fo2) + (0.0746P)2 + 0.9056P]
where P = (Fo2 + 2Fc2)/3
1702 reflections(Δ/σ)max < 0.001
127 parametersΔρmax = 0.34 e Å3
0 restraintsΔρmin = 0.37 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
N10.6440 (3)0.3712 (2)0.4193 (3)0.0570 (10)
H1A0.68230.35390.49030.068*
O10.7060 (2)0.35932 (17)0.1451 (3)0.0622 (9)
H10.73370.37880.07880.093*
O20.5982 (3)0.40892 (19)0.0735 (3)0.0705 (10)
C10.5875 (4)0.3012 (3)0.3587 (5)0.0610 (13)
H1C0.53180.27810.41940.073*
H1D0.64760.26140.34060.073*
C20.5236 (3)0.3211 (2)0.2351 (4)0.0503 (11)
C30.5857 (3)0.3526 (2)0.1324 (4)0.0458 (10)
C40.5273 (4)0.3771 (3)0.0216 (4)0.0553 (12)
C50.4068 (4)0.3686 (3)0.0118 (5)0.0673 (14)
H50.36740.38480.06280.081*
C60.3453 (4)0.3360 (3)0.1131 (6)0.0736 (15)
H60.26380.32960.10680.088*
C70.4024 (4)0.3127 (3)0.2231 (5)0.0694 (14)
H70.35920.29090.29110.083*
C80.5438 (5)0.4325 (3)0.1909 (4)0.0888 (17)
H8A0.60260.45400.24830.133*
H8B0.48510.47250.17340.133*
H8C0.50700.38700.23070.133*
C90.5691 (3)0.4347 (3)0.4576 (4)0.0489 (11)
C100.4534 (4)0.4242 (3)0.4990 (4)0.0609 (12)
H100.42020.37340.49920.073*
C110.3872 (4)0.4887 (3)0.5397 (4)0.0594 (13)
H110.30980.48000.56640.071*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
N10.043 (2)0.077 (3)0.051 (2)0.0053 (19)0.0130 (17)0.011 (2)
O10.0380 (16)0.096 (2)0.0530 (19)0.0043 (15)0.0015 (13)0.0094 (16)
O20.062 (2)0.101 (3)0.048 (2)0.0125 (17)0.0057 (16)0.0070 (19)
C10.048 (3)0.062 (3)0.073 (3)0.003 (2)0.003 (2)0.009 (3)
C20.039 (2)0.050 (3)0.061 (3)0.004 (2)0.004 (2)0.003 (2)
C30.039 (2)0.049 (2)0.049 (3)0.0063 (19)0.006 (2)0.005 (2)
C40.051 (3)0.058 (3)0.057 (3)0.008 (2)0.005 (2)0.009 (2)
C50.052 (3)0.074 (3)0.075 (4)0.015 (2)0.020 (3)0.010 (3)
C60.039 (3)0.081 (4)0.101 (4)0.004 (2)0.013 (3)0.001 (3)
C70.043 (3)0.068 (3)0.097 (4)0.002 (2)0.004 (3)0.016 (3)
C80.097 (4)0.119 (5)0.051 (3)0.025 (3)0.015 (3)0.008 (3)
C90.034 (2)0.072 (3)0.041 (3)0.002 (2)0.0018 (18)0.010 (2)
C100.046 (3)0.068 (3)0.068 (3)0.008 (2)0.005 (2)0.007 (3)
C110.036 (2)0.085 (4)0.057 (3)0.012 (2)0.001 (2)0.002 (3)
Geometric parameters (Å, º) top
N1—C91.414 (5)C5—C61.369 (7)
N1—C11.473 (5)C5—H50.9300
N1—H1A0.9000C6—C71.363 (7)
O1—C31.371 (4)C6—H60.9300
O1—H10.8200C7—H70.9300
O2—C41.375 (5)C8—H8A0.9600
O2—C81.416 (5)C8—H8B0.9600
C1—C21.504 (6)C8—H8C0.9600
C1—H1C0.9700C9—C11i1.375 (6)
C1—H1D0.9700C9—C101.388 (5)
C2—C31.376 (5)C10—C111.378 (6)
C2—C71.383 (5)C10—H100.9300
C3—C41.383 (6)C11—C9i1.375 (6)
C4—C51.374 (6)C11—H110.9300
C9—N1—C1117.1 (3)C4—C5—H5120.4
C9—N1—H1A107.6C7—C6—C5120.7 (4)
C1—N1—H1A107.4C7—C6—H6119.7
C3—O1—H1109.5C5—C6—H6119.7
C4—O2—C8117.8 (4)C6—C7—C2120.9 (5)
N1—C1—C2113.1 (3)C6—C7—H7119.5
N1—C1—H1C109.0C2—C7—H7119.5
C2—C1—H1C109.0O2—C8—H8A109.5
N1—C1—H1D109.0O2—C8—H8B109.5
C2—C1—H1D109.0H8A—C8—H8B109.5
H1C—C1—H1D107.8O2—C8—H8C109.5
C3—C2—C7118.4 (4)H8A—C8—H8C109.5
C3—C2—C1119.5 (3)H8B—C8—H8C109.5
C7—C2—C1121.9 (4)C11i—C9—C10116.7 (4)
O1—C3—C2117.7 (4)C11i—C9—N1119.4 (4)
O1—C3—C4121.8 (4)C10—C9—N1123.8 (4)
C2—C3—C4120.4 (4)C11—C10—C9120.5 (4)
C5—C4—O2124.5 (4)C11—C10—H10119.8
C5—C4—C3120.2 (5)C9—C10—H10119.8
O2—C4—C3115.3 (4)C9i—C11—C10122.8 (4)
C6—C5—C4119.3 (5)C9i—C11—H11118.6
C6—C5—H5120.4C10—C11—H11118.6
C9—N1—C1—C261.1 (5)C2—C3—C4—O2178.8 (3)
N1—C1—C2—C360.7 (5)O2—C4—C5—C6180.0 (4)
N1—C1—C2—C7115.9 (5)C3—C4—C5—C60.3 (7)
C7—C2—C3—O1179.0 (4)C4—C5—C6—C70.5 (7)
C1—C2—C3—O14.3 (6)C5—C6—C7—C20.2 (8)
C7—C2—C3—C41.7 (6)C3—C2—C7—C60.9 (7)
C1—C2—C3—C4174.9 (4)C1—C2—C7—C6175.7 (4)
C8—O2—C4—C51.9 (6)C1—N1—C9—C11i151.6 (4)
C8—O2—C4—C3177.9 (4)C1—N1—C9—C1031.4 (6)
O1—C3—C4—C5179.3 (4)C11i—C9—C10—C110.3 (7)
C2—C3—C4—C51.5 (6)N1—C9—C10—C11177.4 (4)
O1—C3—C4—O20.5 (6)C9—C10—C11—C9i0.4 (7)
Symmetry code: (i) x+1, y+1, z+1.
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
O1—H1···N1ii0.822.152.890 (7)149
N1—H1A···O1iii0.902.042.890 (7)157
Symmetry codes: (ii) x+3/2, y, z1/2; (iii) x+3/2, y, z+1/2.
 

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