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In the crystal structure of the title compound, [(HOC6H4CH(NH3)CH(NH3)C6H4OH]Cl2 or C14H18N2O22+·2Cl, the dication lies about an inversion center at the midpoint of the central C—C bond. The asymmetric unit forms one intramolecular N—H...O hydrogen bond, with an N...O distance of 2.7759 (14) Å, three intermolecular N—H...Cl hydrogen bonds, with N...Cl distances ranging from 3.1343 (10) to 3.3343 (10) Å, and one intermolecular O—H...Cl hydrogen bond, with an O...Cl distance of 3.0142 (9) Å.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536802004920/ya6093sup1.cif
Contains datablocks k01207, I

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536802004920/ya6093Isup2.hkl
Contains datablock I

CCDC reference: 183814

Key indicators

  • Single-crystal X-ray study
  • T = 150 K
  • Mean [sigma](C-C) = 0.002 Å
  • R factor = 0.026
  • wR factor = 0.068
  • Data-to-parameter ratio = 16.9

checkCIF results

No syntax errors found

ADDSYM reports no extra symmetry








Computing details top

Data collection: COLLECT (Nonius BV, 1997-2001); cell refinement: DENZO-SMN (Otwinowski & Minor, 1997); data reduction: DENZO-SMN; program(s) used to solve structure: SHELXTL (Sheldrick, 1999); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL.

meso-1,2-(2-Hydroxyphenyl)-1,2-ethylenediammonium dichloride top
Crystal data top
C14H18N2O22+·2ClDx = 1.461 Mg m3
Mr = 317.20Mo Kα radiation, λ = 0.71073 Å
Trigonal, R3Cell parameters from 1380 reflections
a = 21.8715 (7) Åθ = 2.5–27.5°
c = 7.8297 (3) ŵ = 0.45 mm1
V = 3243.64 (19) Å3T = 150 K
Z = 9Needle, colourless
F(000) = 14940.25 × 0.12 × 0.10 mm
Data collection top
Nonius KappaCCD
diffractometer
1640 independent reflections
Radiation source: fine-focus sealed tube1538 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.020
Detector resolution: 9 pixels mm-1θmax = 27.5°, θmin = 3.2°
φ scans and ω scans with κ offsetsh = 2828
Absorption correction: multi-scan
DENZO-SMN (Otwinowski & Minor, 1997)
k = 2829
Tmin = 0.895, Tmax = 0.956l = 710
4231 measured reflections
Refinement top
Refinement on F2Secondary atom site location: difference Fourier map
Least-squares matrix: fullHydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.026H atoms treated by a mixture of independent and constrained refinement
wR(F2) = 0.068 w = 1/[σ2(Fo2) + (0.0097P)2 + 3.9792P]
where P = (Fo2 + 2Fc2)/3
S = 1.06(Δ/σ)max < 0.001
1640 reflectionsΔρmax = 0.28 e Å3
97 parametersΔρmin = 0.27 e Å3
0 restraintsExtinction correction: SHELXL97, Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
Primary atom site location: structure-invariant direct methodsExtinction coefficient: 0.0020 (6)
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
Cl10.212429 (14)0.264395 (14)0.37680 (3)0.01695 (13)
O10.35544 (5)0.38971 (4)0.49886 (12)0.0213 (2)
C10.41919 (6)0.51335 (6)0.52595 (15)0.0158 (2)
C20.35630 (6)0.45206 (6)0.48185 (15)0.0157 (2)
C30.29891 (6)0.45669 (6)0.42185 (16)0.0186 (3)
H3A0.25610.41490.39420.022*
C40.30403 (7)0.52200 (7)0.40231 (19)0.0253 (3)
H4A0.26500.52500.35950.030*
C50.36618 (7)0.58318 (7)0.4453 (2)0.0293 (3)
H5A0.36960.62800.43220.035*
C60.42322 (6)0.57865 (6)0.50728 (18)0.0224 (3)
H6A0.46550.62050.53740.027*
C70.48415 (6)0.50996 (6)0.57596 (14)0.0154 (2)
H70.52060.55780.61720.018*
N10.47017 (5)0.45783 (5)0.71739 (13)0.0177 (2)
H1A0.51180.46720.76560.027*
H1B0.44800.41330.67390.027*
H1C0.44230.46160.79810.027*
H1O0.3132 (10)0.3542 (10)0.462 (2)0.043 (5)*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Cl10.01538 (17)0.01685 (17)0.01810 (19)0.00768 (11)0.00131 (9)0.00108 (10)
O10.0178 (4)0.0145 (4)0.0300 (5)0.0070 (3)0.0052 (4)0.0013 (3)
C10.0140 (5)0.0179 (5)0.0161 (5)0.0083 (4)0.0015 (4)0.0009 (4)
C20.0164 (5)0.0160 (5)0.0148 (5)0.0082 (4)0.0018 (4)0.0001 (4)
C30.0133 (5)0.0198 (6)0.0207 (6)0.0067 (4)0.0004 (4)0.0008 (5)
C40.0180 (6)0.0252 (6)0.0360 (7)0.0134 (5)0.0007 (5)0.0016 (5)
C50.0232 (6)0.0189 (6)0.0489 (9)0.0128 (5)0.0008 (6)0.0022 (6)
C60.0165 (6)0.0166 (6)0.0322 (7)0.0069 (5)0.0004 (5)0.0015 (5)
C70.0143 (5)0.0149 (5)0.0154 (5)0.0061 (4)0.0003 (4)0.0010 (4)
N10.0160 (5)0.0212 (5)0.0153 (5)0.0089 (4)0.0008 (4)0.0003 (4)
Geometric parameters (Å, º) top
O1—C21.3607 (14)C5—C61.3876 (18)
O1—H1O0.91 (2)C5—H5A0.9500
C1—C61.3941 (16)C6—H6A0.9500
C1—C21.4015 (16)C7—N11.5070 (15)
C1—C71.5108 (15)C7—C7i1.545 (2)
C2—C31.3907 (16)C7—H71.0000
C3—C41.3842 (17)N1—H1A0.9100
C3—H3A0.9500N1—H1B0.9100
C4—C51.3902 (18)N1—H1C0.9100
C4—H4A0.9500
C2—O1—H1O109.0 (12)C5—C6—C1120.75 (11)
C6—C1—C2118.89 (10)C5—C6—H6A119.6
C6—C1—C7119.88 (10)C1—C6—H6A119.6
C2—C1—C7120.95 (10)N1—C7—C1112.80 (9)
O1—C2—C3123.05 (10)N1—C7—C7i107.59 (11)
O1—C2—C1116.72 (10)C1—C7—C7i112.32 (12)
C3—C2—C1120.23 (10)N1—C7—H7108.0
C4—C3—C2120.15 (11)C1—C7—H7108.0
C4—C3—H3A119.9C7i—C7—H7108.0
C2—C3—H3A119.9C7—N1—H1A109.5
C3—C4—C5120.14 (11)C7—N1—H1B109.5
C3—C4—H4A119.9H1A—N1—H1B109.5
C5—C4—H4A119.9C7—N1—H1C109.5
C6—C5—C4119.82 (12)H1A—N1—H1C109.5
C6—C5—H5A120.1H1B—N1—H1C109.5
C4—C5—H5A120.1
Symmetry code: (i) x+1, y+1, z+1.
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N1—H1A···Cl1ii0.912.533.3344 (10)148
N1—H1B···O10.912.282.7759 (14)114
N1—H1B···Cl1iii0.912.553.3724 (10)150
N1—H1C···Cl1iv0.912.253.1343 (10)163
O1—H1O···Cl10.91 (2)2.20 (2)3.1042 (9)177.2 (17)
Symmetry codes: (ii) xy+2/3, x+1/3, z+4/3; (iii) y+2/3, xy+1/3, z+1/3; (iv) x+y+1/3, x+2/3, z+2/3.
 

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