In the crystal structure of the title compound, [(HOC
6H
4CH(NH
3)CH(NH
3)C
6H
4OH]Cl
2 or C
14H
18N
2O
22+·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
CCDC reference: 183814
Key indicators
- Single-crystal X-ray study
- T = 150 K
- Mean (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
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+·2Cl− | Dx = 1.461 Mg m−3 |
Mr = 317.20 | Mo Kα radiation, λ = 0.71073 Å |
Trigonal, R3 | Cell parameters from 1380 reflections |
a = 21.8715 (7) Å | θ = 2.5–27.5° |
c = 7.8297 (3) Å | µ = 0.45 mm−1 |
V = 3243.64 (19) Å3 | T = 150 K |
Z = 9 | Needle, colourless |
F(000) = 1494 | 0.25 × 0.12 × 0.10 mm |
Data collection top
Nonius KappaCCD diffractometer | 1640 independent reflections |
Radiation source: fine-focus sealed tube | 1538 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.020 |
Detector resolution: 9 pixels mm-1 | θmax = 27.5°, θmin = 3.2° |
φ scans and ω scans with κ offsets | h = −28→28 |
Absorption correction: multi-scan DENZO-SMN (Otwinowski & Minor, 1997) | k = −28→29 |
Tmin = 0.895, Tmax = 0.956 | l = −7→10 |
4231 measured reflections | |
Refinement top
Refinement on F2 | Secondary atom site location: difference Fourier map |
Least-squares matrix: full | Hydrogen site location: inferred from neighbouring sites |
R[F2 > 2σ(F2)] = 0.026 | H 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 reflections | Δρmax = 0.28 e Å−3 |
97 parameters | Δρmin = −0.27 e Å−3 |
0 restraints | Extinction correction: SHELXL97, Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4 |
Primary atom site location: structure-invariant direct methods | Extinction 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 | x | y | z | Uiso*/Ueq | |
Cl1 | 0.212429 (14) | 0.264395 (14) | 0.37680 (3) | 0.01695 (13) | |
O1 | 0.35544 (5) | 0.38971 (4) | 0.49886 (12) | 0.0213 (2) | |
C1 | 0.41919 (6) | 0.51335 (6) | 0.52595 (15) | 0.0158 (2) | |
C2 | 0.35630 (6) | 0.45206 (6) | 0.48185 (15) | 0.0157 (2) | |
C3 | 0.29891 (6) | 0.45669 (6) | 0.42185 (16) | 0.0186 (3) | |
H3A | 0.2561 | 0.4149 | 0.3942 | 0.022* | |
C4 | 0.30403 (7) | 0.52200 (7) | 0.40231 (19) | 0.0253 (3) | |
H4A | 0.2650 | 0.5250 | 0.3595 | 0.030* | |
C5 | 0.36618 (7) | 0.58318 (7) | 0.4453 (2) | 0.0293 (3) | |
H5A | 0.3696 | 0.6280 | 0.4322 | 0.035* | |
C6 | 0.42322 (6) | 0.57865 (6) | 0.50728 (18) | 0.0224 (3) | |
H6A | 0.4655 | 0.6205 | 0.5374 | 0.027* | |
C7 | 0.48415 (6) | 0.50996 (6) | 0.57596 (14) | 0.0154 (2) | |
H7 | 0.5206 | 0.5578 | 0.6172 | 0.018* | |
N1 | 0.47017 (5) | 0.45783 (5) | 0.71739 (13) | 0.0177 (2) | |
H1A | 0.5118 | 0.4672 | 0.7656 | 0.027* | |
H1B | 0.4480 | 0.4133 | 0.6739 | 0.027* | |
H1C | 0.4423 | 0.4616 | 0.7981 | 0.027* | |
H1O | 0.3132 (10) | 0.3542 (10) | 0.462 (2) | 0.043 (5)* | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
Cl1 | 0.01538 (17) | 0.01685 (17) | 0.01810 (19) | 0.00768 (11) | −0.00131 (9) | 0.00108 (10) |
O1 | 0.0178 (4) | 0.0145 (4) | 0.0300 (5) | 0.0070 (3) | −0.0052 (4) | −0.0013 (3) |
C1 | 0.0140 (5) | 0.0179 (5) | 0.0161 (5) | 0.0083 (4) | 0.0015 (4) | −0.0009 (4) |
C2 | 0.0164 (5) | 0.0160 (5) | 0.0148 (5) | 0.0082 (4) | 0.0018 (4) | 0.0001 (4) |
C3 | 0.0133 (5) | 0.0198 (6) | 0.0207 (6) | 0.0067 (4) | 0.0004 (4) | −0.0008 (5) |
C4 | 0.0180 (6) | 0.0252 (6) | 0.0360 (7) | 0.0134 (5) | −0.0007 (5) | 0.0016 (5) |
C5 | 0.0232 (6) | 0.0189 (6) | 0.0489 (9) | 0.0128 (5) | −0.0008 (6) | 0.0022 (6) |
C6 | 0.0165 (6) | 0.0166 (6) | 0.0322 (7) | 0.0069 (5) | 0.0004 (5) | −0.0015 (5) |
C7 | 0.0143 (5) | 0.0149 (5) | 0.0154 (5) | 0.0061 (4) | 0.0003 (4) | −0.0010 (4) |
N1 | 0.0160 (5) | 0.0212 (5) | 0.0153 (5) | 0.0089 (4) | 0.0008 (4) | 0.0003 (4) |
Geometric parameters (Å, º) top
O1—C2 | 1.3607 (14) | C5—C6 | 1.3876 (18) |
O1—H1O | 0.91 (2) | C5—H5A | 0.9500 |
C1—C6 | 1.3941 (16) | C6—H6A | 0.9500 |
C1—C2 | 1.4015 (16) | C7—N1 | 1.5070 (15) |
C1—C7 | 1.5108 (15) | C7—C7i | 1.545 (2) |
C2—C3 | 1.3907 (16) | C7—H7 | 1.0000 |
C3—C4 | 1.3842 (17) | N1—H1A | 0.9100 |
C3—H3A | 0.9500 | N1—H1B | 0.9100 |
C4—C5 | 1.3902 (18) | N1—H1C | 0.9100 |
C4—H4A | 0.9500 | | |
| | | |
C2—O1—H1O | 109.0 (12) | C5—C6—C1 | 120.75 (11) |
C6—C1—C2 | 118.89 (10) | C5—C6—H6A | 119.6 |
C6—C1—C7 | 119.88 (10) | C1—C6—H6A | 119.6 |
C2—C1—C7 | 120.95 (10) | N1—C7—C1 | 112.80 (9) |
O1—C2—C3 | 123.05 (10) | N1—C7—C7i | 107.59 (11) |
O1—C2—C1 | 116.72 (10) | C1—C7—C7i | 112.32 (12) |
C3—C2—C1 | 120.23 (10) | N1—C7—H7 | 108.0 |
C4—C3—C2 | 120.15 (11) | C1—C7—H7 | 108.0 |
C4—C3—H3A | 119.9 | C7i—C7—H7 | 108.0 |
C2—C3—H3A | 119.9 | C7—N1—H1A | 109.5 |
C3—C4—C5 | 120.14 (11) | C7—N1—H1B | 109.5 |
C3—C4—H4A | 119.9 | H1A—N1—H1B | 109.5 |
C5—C4—H4A | 119.9 | C7—N1—H1C | 109.5 |
C6—C5—C4 | 119.82 (12) | H1A—N1—H1C | 109.5 |
C6—C5—H5A | 120.1 | H1B—N1—H1C | 109.5 |
C4—C5—H5A | 120.1 | | |
Symmetry code: (i) −x+1, −y+1, −z+1. |
Hydrogen-bond geometry (Å, º) top
D—H···A | D—H | H···A | D···A | D—H···A |
N1—H1A···Cl1ii | 0.91 | 2.53 | 3.3344 (10) | 148 |
N1—H1B···O1 | 0.91 | 2.28 | 2.7759 (14) | 114 |
N1—H1B···Cl1iii | 0.91 | 2.55 | 3.3724 (10) | 150 |
N1—H1C···Cl1iv | 0.91 | 2.25 | 3.1343 (10) | 163 |
O1—H1O···Cl1 | 0.91 (2) | 2.20 (2) | 3.1042 (9) | 177.2 (17) |
Symmetry codes: (ii) x−y+2/3, x+1/3, −z+4/3; (iii) −y+2/3, x−y+1/3, z+1/3; (iv) −x+y+1/3, −x+2/3, z+2/3. |