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Acta Cryst. (2003). E59, o1314-o1317
https://doi.org/10.1107/S1600536803017926
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Tris(2-ammonio­ethyl)­amine tris({2-[(2,6-di­chloro­phenyl)­amino]­phenyl}acetate) hexahydrate

D. E. Lynch, A. S. Bening and S. Parsons
The structure of the title compound, C6H21N43+·3C14H10Cl2NO2-·6H2O, comprises the 1:3 organic salt of tris(2-ethyl­amine)­amine and diclofenac acid, with an approximated six water mol­ecules in an extensive hydrogen-bonding network. Two water mol­ecules exist as full-occupancy mol­ecules but the remainder are all disordered with partial occupancies. Disorder is also present in the base mol­ecule, with the ammonium group of one 2-ammonio­ethyl arm unequally disordered over two sites.
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Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536803017926/wn6172sup1.cif
Contains datablocks I, global

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536803017926/wn6172Isup2.hkl
Contains datablock I

CCDC reference: 222868

checkCIF report

Key indicators

  • Single-crystal X-ray study
  • T = 150 K
  • Mean [sigma](C-C) = 0.007 Å
  • H-atom completeness 85%
  • Disorder in solvent or counterion
  • R factor = 0.070
  • wR factor = 0.222
  • Data-to-parameter ratio = 13.0

checkCIF/PLATON results

No syntax errors found




Alert level A
PLAT029_ALERT_3_A _diffrn_measured_fraction_theta_full Low .....       0.94
PLAT052_ALERT_1_A (Proper) Absorption Correction Method Missing           ?
PLAT430_ALERT_2_A Short Inter D...A Contact:O2D     .. O5      =       2.27 Ang.
Author Response: This I have covered in the text. I suspect that with the nature of the partial occupancies of the water molecules, which includes O5, that this distance is an artifact of the refinement. 

Alert level B
PLAT430_ALERT_2_B Short Inter D...A Contact:O1B     .. O6      =       2.65 Ang.
Author Response: This I have covered in the text. I suspect that with the nature of the partial occupancies of the water molecules, which includes O5, that this distance is an artifact of the refinement. 
PLAT430_ALERT_2_B Short Inter D...A Contact:O1C     .. O11     =       2.76 Ang.
Author Response: This I have covered in the text. I suspect that with the nature of the partial occupancies of the water molecules, which includes O5, that this distance is an artifact of the refinement. 
PLAT430_ALERT_2_B Short Inter D...A Contact:O2B     .. O8      =       2.66 Ang.
Author Response: This I have covered in the text. I suspect that with the nature of the partial occupancies of the water molecules, which includes O5, that this distance is an artifact of the refinement. 
PLAT430_ALERT_2_B Short Inter D...A Contact:O2B     .. O7      =       2.70 Ang.
Author Response: This I have covered in the text. I suspect that with the nature of the partial occupancies of the water molecules, which includes O5, that this distance is an artifact of the refinement. 
PLAT430_ALERT_2_B Short Inter D...A Contact:O2D     .. O6      =       2.79 Ang.
Author Response: This I have covered in the text. I suspect that with the nature of the partial occupancies of the water molecules, which includes O5, that this distance is an artifact of the refinement. 
PLAT432_ALERT_2_B Short Inter X...Y Contact:C8A     .. O6      =       2.86 Ang.
PLAT432_ALERT_2_B Short Inter X...Y Contact:C9A     .. O6      =       2.81 Ang.


Alert level C
PLAT041_ALERT_1_C Calc. and Rep. SumFormula Strings    Differ ..          ?
PLAT042_ALERT_1_C Calc. and Rep. MoietyFormula Strings Differ ..          ?
PLAT057_ALERT_3_C Correction for Absorption Required   RT(exp) =       1.16
PLAT063_ALERT_3_C Crystal Probably too Large for Beam Size .....       0.77 mm
PLAT068_ALERT_1_C Reported F000 Differs from Calcd (or Missing).          ?
PLAT125_ALERT_4_C No _symmetry_space_group_name_Hall Given .....          ?
PLAT241_ALERT_2_C Check High   U(eq) as Compared to Neighbors ..          C5A
PLAT242_ALERT_2_C Check Low    U(eq) as Compared to Neighbors ..         C14B
PLAT301_ALERT_3_C Main Residue  Disorder .......................       1.00 Perc.
PLAT302_ALERT_4_C Anion/Solvent Disorder .......................      31.00 Perc.
PLAT311_ALERT_2_C Isolated Disordered Oxygen Atom (No H's ?) ...          >O7
PLAT311_ALERT_2_C Isolated Disordered Oxygen Atom (No H's ?) ...          <O8
PLAT311_ALERT_2_C Isolated Disordered Oxygen Atom (No H's ?) ...         <O13
PLAT311_ALERT_2_C Isolated Disordered Oxygen Atom (No H's ?) ...          <O3
PLAT340_ALERT_3_C Low Bond Precision on C-C bonds (x 1000) Ang..          7
PLAT417_ALERT_2_C Short Inter D-H..H-D      H11     .. H42A    =       2.10 Ang.
PLAT417_ALERT_2_C Short Inter D-H..H-D      H21     .. H76A    =       2.14 Ang.
PLAT430_ALERT_2_C Short Inter D...A Contact:O1B     .. O5      =       2.85 Ang.
Author Response: This I have covered in the text. I suspect that with the nature of the partial occupancies of the water molecules, which includes O5, that this distance is an artifact of the refinement. 
PLAT432_ALERT_2_C Short Inter X...Y Contact:O2D     .. C9A     =       2.98 Ang.
PLAT751_ALERT_4_C Bond    Calc     0.81714, Rep    0.817(4) ....  Senseless su
              O1   -H11     1.555   1.555
PLAT751_ALERT_4_C Bond    Calc     0.81929, Rep    0.820(4) ....  Senseless su
              O1   -H12     1.555   1.555
PLAT751_ALERT_4_C Bond    Calc     0.89371, Rep    0.894(6) ....  Senseless su
              O2   -H21     1.555   1.555
PLAT751_ALERT_4_C Bond    Calc     0.82600, Rep    0.826(5) ....  Senseless su
              O2   -H22     1.555   1.555
PLAT752_ALERT_4_C Angle   Calc      124.01, Rep    124.0(5) ....  Senseless su
              H11  -O1   -H12     1.555   1.555   1.555
PLAT752_ALERT_4_C Angle   Calc      100.48, Rep    100.5(7) ....  Senseless su
              H21  -O2   -H22     1.555   1.555   1.555
PLAT755_ALERT_4_C D-H     Calc     0.81714, Rep    0.817(4) ....  Senseless su
              O1   -H11     1.555   1.555
PLAT755_ALERT_4_C D-H     Calc     0.81929, Rep    0.820(4) ....  Senseless su
              O1   -H12     1.555   1.555
PLAT755_ALERT_4_C D-H     Calc     0.89371, Rep    0.894(6) ....  Senseless su
              O2   -H21     1.555   1.555
PLAT755_ALERT_4_C D-H     Calc     0.89371, Rep    0.894(6) ....  Senseless su
              O2   -H21     1.555   1.555
PLAT755_ALERT_4_C D-H     Calc     0.82600, Rep    0.826(5) ....  Senseless su
              O2   -H22     1.555   1.555
PLAT756_ALERT_4_C H...A   Calc     1.90942, Rep    1.909(4) ....  Senseless su
              H11  -O1C     1.555   2.555
PLAT756_ALERT_4_C H...A   Calc     1.87799, Rep    1.878(4) ....  Senseless su
              H12  -O2B     1.555   2.555
PLAT756_ALERT_4_C H...A   Calc     1.90617, Rep    1.906(4) ....  Senseless su
              H22  -O1D     1.555   2.555
PLAT764_ALERT_4_C Overcomplete CIF Bond list Detected (Rep/Expd)       1.11 Ratio


Alert level G
FORMU01_ALERT_2_G  There is a discrepancy between the atom counts in the
            _chemical_formula_sum and the formula from the _atom_site* data.
            Atom count from _chemical_formula_sum:C48 H63 Cl6 N7 O12
            Atom count from the _atom_site data:  C48 H53 Cl6 N7 O12
CELLZ01_ALERT_1_G Difference between formula and atom_site contents detected.
CELLZ01_ALERT_1_G WARNING: H atoms missing from atom site list. Is this intentional?
           From the CIF: _cell_formula_units_Z    4
           From the CIF: _chemical_formula_sum  C48 H63 Cl6 N7 O12
           TEST: Compare cell contents of formula and atom_site data

           atom    Z*formula  cif sites diff
           C        192.00    192.00    0.00
           H        252.00    212.00   40.00
           Cl        24.00     24.00    0.00
           N         28.00     28.00    0.00
           O         48.00     48.00    0.00


   3 ALERT level A = In general: serious problem
   7 ALERT level B = Potentially serious problem
  34 ALERT level C = Check and explain
   3 ALERT level G = General alerts; check

   6 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
  19 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
  17 ALERT type 4 Improvement, methodology, query or suggestion
Comment top

{2-[(2,6-Dichlorophenyl)amino]phenyl}acetic acid, or diclofenac acid, was first synthesized in 1966 in the Netherlands (Calabro & Ehrlich, 1986). Diclofenac acid is most commonly used as a non-steroidal anti-inflammatory drug but also shows analgesic and antipyretic properties. The sodium salt of diclofenac acid is sold commercially as Voltaren, whereas the potassium salt is marketed as Cataflam. The molecular structure of diclofenac acid consists of a phenylacetic acid group, linked by a secondary amino group to a 2,6-dichlorophenyl group; there is the potential for maximum twist between the two rings. The dihedral angle between these rings is of great importance to the pharmacological activity of diclofenac acid. To obtain optimal activity, the two rings should be twisted as much as possible, so that the carboxylate group of the drug can bind to arachidonic acid, thus preventing the binding of the enzyme COX-2 which propagates inflammation (Castellari & Sabatino, 1994; Castellari & Ottani, 1997b).

A search of the April 2003 release of the Cambridge Structural Database (Allen, 2002) reveals that the crystal structure of diclofenac acid has been reported five times [Moser et al., 1990; Kovala-Demertzi et al., 1993; Castellari & Ottani, 1997b (2 polymorphic forms); Jaiboon et al., 2001]. Moreover, in attempts to improve the structural characteristics of diclofenac acid, organic salts have been prepared, using small aliphatic bases, and their structures studied. Thus far, these bases include N-(2-hydroxyethyl)pyrrolidine (Castellari & Sabatino, 1994), N-(2-hydroxyethyl)piperazine, N-(2-hydroxyethyl)piperidine, N-(2-hydroxyethyl)morpholine (Castellari & Sabatino, 1996a), bis(2-hydroxyethyl)amine (Castellari & Ottani, 1995), tris(2-hydroxyethyl)amine (Castellari & Sabatino, 1996b), tris(2-hydroxymethyl)methylamine (Castellari & Ottani, 1997a), piperazine (Castellari & Ottani, 1998), diethylamine (Pomes-Hernandez et al., 1997; Castellari et al., 2000, 2001a) and pyrrolidine (Castellari et al., 2001b). Here we report the 1:3 organic salt hexahydrate of tris(2-ethylamine)amine with diclofenac acid in an attempt to extend the use of small aliphatic bases to improve the structural characteristics of diclofenac acid.

The asymmetric unit of (I) comprises the 1:3 organic salt of tris(2-ethylamine)amine and diclofenac acid, with an approximated six water molecules (Fig. 1). Two of those water molecules, O1 and O2, exist as full-occupancy molecules but the remainder are all disordered with partial occupancies. Atoms O3 and O4 are associated as a disordered pair (O···O distances are listed in Table 1), with occupancies of 0.20 (2) and 0.50 (2), respectively, while O5 and O6 are also associated as a disordered pair, each with an occupancy of 0.30 (2). Fragments O7–O13 are associated with each other and the respective occupancies are 0.70 (2), 0.20 (2), 0.30 (2), 0.50 (2), 0.50 (2), 0.30 (2) and 0.20 (2). Extensive refinement was required to determine each of these values and the total number of water molecules was determined to the nearest half-water molecule; thus, to satisfy the electron-density map there are 6.0 (5) water molecules. The three highest unassigned peaks in the difference map are greater than 0.60 e Å−3; they are 0.70 e Å−3 at 1.17 Å from C6A, 0.65 e Å−3 at 1.55 Å from N10A, and 0.64 e Å−3 at 1.05 Å from C9A. Although no H atoms were located on C6A (or positioned geometrically), the residual peak close to C6A is not in a suitable position to be considered as one. Furthermore, removing the disordered fragments and calculating the void space that is left can afford a rough approximation to the number of water molecules. Thus, removal of O3–O13 leaves a void space of 482 Å3 per unit cell; assuming 40 Å3 per hydrogen-bonded water molecule, this corresponds to 12 full water molecules or three full molecules per asymmetric unit, giving a total of five water molecules per asymmetric unit. However, the displacement parameters for the water fragments could not sustain realistic occupancies that totalled only three full water molecules. Interestingly, two recent structures (Lynch, 2003a, 2003b), also containing tris(2-ethylamine)amine and benzoic acid derivatives, crystallized with 5.5 and four water molecules, respectively, in their asymmetric units.

The existence of ten water fragments in the hydrogen-bonding network and the difficultly involved with the assignment of H atoms to each has caused certain problems. The formal assignment of hydrogen-bonding associations is listed in Table 2, but does not include the D···A distances for the disordered water fragments. Atom O3 is 2.227 Å from O5, 2.780 Å from O6, 3.023 Å from O2D, and 3.149 Å from N72A. Atom O4 is 2.566 Å from N72A, 2.733 Å from O5, 3.063 Å from O2C, 3.182 Å from O2D, and 3.236 Å from O6. O5 is 2.271 Å from O2D and 2.846 Å from O1B. Atom O6 is 1.828 Å from N71A, 2.647 Å from O1B, and 2.787 Å from O2D. Atom O7 is 2.697 Å from O2B, 2.751 Å from N10A, and 3.196 Å from N71A. Atom O8 is 2.805 Å from O11, 2.654 Å from O2B, 2.794 Å from N72A, 2.832 Å from N71A, and 3.228 Å from N10A. Atom O10 is 2.988 Å from O11 and 3.122 Å from O2B. Atom O11 is 3.233 Å from O13, 2.760 Å from O1C, 3.055 Å from N72A, and 3.128 Å and 3.340 Å from N4A. Atom O12 is 2.749 Å from N72A and 3.183 Å from O1C. Atom O13 is 3.027 Å from O2B. The majority of these distances are appropriate for normal D—H···A associations, although some are slightly short. However, the `problem' distance is that between O5 and O2D, 2.271 Å. Atom O5 has an occupancy of 0.30 (2), and is too heavy to be a partial-occupancy H atom but there does not seem to be any obvious explanation.

Disorder is also present in the base molecule, with the ammonium group of one 2-ammonioethyl arm disordered over two sites, N71A and N72A, with occupancies of 0.70 (2) and 0.30 (2), respectively. In all known structures where tris(2-ammonioethyl)amine is used as an organic base and not as a ligand, the base molecule adopts a tripod conformation, as it does when containing a metal centre. In the title structure, the tris(2-ammonioethyl)amine adopts two conformations, with the major one, occupancy = 0.70 (2), having one arm twisted away from the rest of the molecule; this contrasts with the minor conformation that adopts the standard tripod shape of previously reported structures. The dihedral angles between the two aromatic rings in the three diclofenac acid molecules are 59.57 (15)° for molecule B, 59.25 (14)° for molecule C and 58.92 (15)° for molecule D; these values are low compared to those in the previously reported structures of diclofenac acid (range 59–74°), including the salt structures.

Experimental top

Tris(2-aminoethyl)amine and diclofenac acid (1:3 molar ratio) were refluxed in ethanol for 20 min. Total evaporation of the solvent gave colourless prisms (m.p. 422 K).

Refinement top

All amine H atoms were initially located in difference syntheses, but were then included in the refinement (along with all non-water H atoms), at calculated positions, in the riding-model approximation, with N—H set to 0.88 Å (NH) and 0.91 Å (NH3+), and C—H set to 0.99 Å (CH2) and 0.95 Å (Ar—H). The isotropic displacement parameters were set equal to 1.25Ueq of the carrier atom. The H atoms for O1 and O2 were included in the refinement at calculated positions, while the isotropic displacement parameters were set equal to 1.25Ueq(O). No H atoms on C6A or any of the water fragments (O3–O13) were either located or positioned geometrically. Poor crystal quality restricted the measured data to only 94% of the possible total.

Computing details top

Data collection: DIF4 (Stoe & Cie, 1990); cell refinement: DIF4; data reduction: REDU4 (Stoe & Cie, 1990); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: PLATON97 (Spek, 1997); software used to prepare material for publication: SHELXL97.

Figures top
[Figure 1] Fig. 1. The molecular configuration and atom-numbering scheme for the title compound. Displacement ellipsoids are drawn at the 50% probability level.
Tris(2-ammonioethyl)amine tris({2-[(2,6-dichlorophenyl)amino]phenyl}acetate) hexahydrate top
Crystal data top
C6H21N43+·3C14H10Cl2NO2−·6H2ODx = 1.401 Mg m−3
Mr = 1142.75Melting point: 453 K K
Monoclinic, P21/nMo Kα radiation, λ = 0.71073 Å
a = 22.677 (4) ÅCell parameters from 48 reflections
b = 9.3735 (17) Åθ = 15–16°
c = 26.415 (5) ŵ = 0.38 mm−1
β = 105.176 (17)°T = 150 K
V = 5419.0 (18) Å3Prism, colourless
Z = 40.77 × 0.58 × 0.31 mm
F(000) = 2392
Data collection top
Stoe Stadi-4
diffractometer		5678 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tubeRint = 0.025
Graphite monochromatorθmax = 25.0°, θmin = 2.6°
ω/θ scansh = −26→26
Absorption correction: ψ scan
(Stoe & Cie, 1995)		k = 0→11
Tmin = 0.757, Tmax = 0.891l = 0→31
9857 measured reflections3 standard reflections every 60 min
9532 independent reflections intensity decay: 3%
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)] = 0.070Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.222H atoms treated by a mixture of independent and constrained refinement
S = 1.02 w = 1/[σ2(Fo2) + (0.1165P)2 + 6.6139P]
where P = (Fo2 + 2Fc2)/3
9532 reflections(Δ/σ)max < 0.001
734 parametersΔρmax = 0.70 e Å−3
100 restraintsΔρmin = −0.50 e Å−3
Crystal data top
C6H21N43+·3C14H10Cl2NO2−·6H2OV = 5419.0 (18) Å3
Mr = 1142.75Z = 4
Monoclinic, P21/nMo Kα radiation
a = 22.677 (4) ŵ = 0.38 mm−1
b = 9.3735 (17) ÅT = 150 K
c = 26.415 (5) Å0.77 × 0.58 × 0.31 mm
β = 105.176 (17)°
Data collection top
Stoe Stadi-4
diffractometer		5678 reflections with I > 2σ(I)
Absorption correction: ψ scan
(Stoe & Cie, 1995)		Rint = 0.025
Tmin = 0.757, Tmax = 0.8913 standard reflections every 60 min
9857 measured reflections intensity decay: 3%
9532 independent reflections
Refinement top
R[F2 > 2σ(F2)] = 0.070100 restraints
wR(F2) = 0.222H atoms treated by a mixture of independent and constrained refinement
S = 1.02Δρmax = 0.70 e Å−3
9532 reflectionsΔρmin = −0.50 e Å−3
734 parameters
Special details top

Geometry. Mean plane data ex SHELXL97 for molecule (I) ############################################

Least-squares planes (x,y,z in crystal coordinates) and deviations from them (* indicates atom used to define plane)

- 6.4009 (0.0399) x + 0.8654 (0.0181) y + 26.2959 (0.0092) z = 11.3239 (0.0137)

* −0.0070 (0.0031) C1B * 0.0040 (0.0033) C2B * 0.0027 (0.0035) C3B * −0.0065 (0.0035) C4B * 0.0035 (0.0034) C5B * 0.0033 (0.0032) C6B

Rms deviation of fitted atoms = 0.0048

9.3070 (0.0374) x + 6.5650 (0.0122) y + 12.0496 (0.0436) z = 9.0379 (0.0207)

Angle to previous plane (with approximate e.s.d.) = 59.57 (0.15)

* 0.0277 (0.0029) C7B * −0.0094 (0.0031) C8B * −0.0157 (0.0032) C9B * 0.0223 (0.0032) C10B * −0.0029 (0.0031) C11B * −0.0221 (0.0030) C12B

Rms deviation of fitted atoms = 0.0187

− 6.9839 (0.0389) x − 0.6825 (0.0180) y + 26.3136 (0.0090) z = 7.5474 (0.0082)

Angle to previous plane (with approximate e.s.d.) = 67.88 (0.14)

* −0.0099 (0.0031) C1C * 0.0028 (0.0033) C2C * 0.0055 (0.0034) C3C * −0.0067 (0.0034) C4C * −0.0004 (0.0035) C5C * 0.0088 (0.0033) C6C

Rms deviation of fitted atoms = 0.0065

8.8881 (0.0376) x − 6.4251 (0.0124) y + 12.9331 (0.0417) z = 2.5395 (0.0196)

Angle to previous plane (with approximate e.s.d.) = 59.25 (0.14)

* 0.0256 (0.0029) C7C * −0.0099 (0.0031) C8C * −0.0129 (0.0031) C9C * 0.0199 (0.0032) C10C * −0.0031 (0.0031) C11C * −0.0196 (0.0030) C12C

Rms deviation of fitted atoms = 0.0169

− 7.6414 (0.0388) x + 1.1039 (0.0174) y + 26.1449 (0.0105) z = 4.6210 (0.0048)

Angle to previous plane (with approximate e.s.d.) = 68.88 (0.13)

* −0.0110 (0.0031) C1D * 0.0035 (0.0032) C2D * 0.0079 (0.0035) C3D * −0.0117 (0.0035) C4D * 0.0041 (0.0033) C5D * 0.0072 (0.0032) C6D

Rms deviation of fitted atoms = 0.0082

9.2711 (0.0382) x + 6.3187 (0.0128) y + 12.8562 (0.0431) z = 2.1119 (0.0084)

Angle to previous plane (with approximate e.s.d.) = 58.92 (0.15)

* 0.0328 (0.0030) C7D * −0.0129 (0.0031) C8D * −0.0135 (0.0032) C9D * 0.0202 (0.0032) C10D * 0.0008 (0.0031) C11D * −0.0275 (0.0031) C12D

Rms deviation of fitted atoms = 0.0208

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/UeqOcc. (<1)
N1A0.6834 (2)0.8791 (7)0.1158 (2)0.0651 (17)
C2A0.6713 (3)0.8594 (8)0.0590 (2)0.0524 (17)
H21A0.70440.80180.05120.065*
H22A0.67080.95350.04190.065*
C3A0.6116 (3)0.7866 (8)0.0372 (2)0.0587 (19)
H31A0.61100.69400.05510.073*
H32A0.60550.7682−0.00070.073*
N4A0.5613 (2)0.8811 (6)0.0456 (2)0.0586 (15)
H41A0.56740.89830.08050.073*
H42A0.52460.83710.03300.073*
H43A0.56150.96520.02840.073*
C5A0.7180 (3)1.0028 (12)0.1374 (3)0.100 (3)
H51A0.75201.01670.12080.125*
H52A0.73570.98990.17550.125*
C6A0.6756 (3)1.1349 (9)0.1273 (4)0.088 (3)
N71A0.7066 (4)1.2778 (11)0.1478 (3)0.078 (3)0.70
H71A0.74751.26390.16080.097*0.70
H72A0.69061.31190.17360.097*0.70
H73A0.70001.34190.12100.097*0.70
N72A0.6217 (8)1.126 (2)0.1526 (7)0.067 (6)0.30
H74A0.60121.04270.14310.084*0.30
H75A0.59601.20080.14160.084*0.30
H76A0.63621.12920.18820.084*0.30
C8A0.7170 (3)0.7479 (9)0.1429 (3)0.077 (2)
H81A0.70600.66500.11910.096*
H82A0.76150.76370.14950.096*
C9A0.7028 (4)0.7130 (10)0.1939 (3)0.087 (2)
H91A0.72900.63300.21100.109*
H92A0.71210.79680.21740.109*
N10A0.6358 (3)0.6719 (7)0.1856 (2)0.081 (2)
H11A0.61180.74920.17400.101*
H12A0.62960.64130.21640.101*
H13A0.62610.60080.16140.101*
Cl1B0.34609 (6)−0.21282 (13)0.59379 (5)0.0333 (3)
Cl2B0.37814 (5)0.04546 (12)0.41896 (4)0.0264 (3)
O1B0.21500 (17)0.0302 (5)0.55915 (15)0.0586 (13)
O2B0.1240 (2)0.1154 (6)0.5240 (2)0.0846 (19)
N1B0.31522 (16)0.0010 (4)0.50707 (15)0.0240 (9)
H1B0.2821−0.04530.50890.030*
C1B0.3118 (2)0.1528 (5)0.50124 (17)0.0234 (10)
C2B0.2540 (2)0.2154 (5)0.48554 (18)0.0260 (11)
C3B0.2510 (2)0.3635 (5)0.47988 (19)0.0323 (12)
H3B0.21210.40790.46920.040*
C4B0.3028 (3)0.4475 (5)0.4894 (2)0.0362 (13)
H4B0.29950.54790.48480.045*
C5B0.3597 (2)0.3836 (5)0.50569 (19)0.0305 (12)
H5B0.39560.44050.51280.038*
C6B0.3643 (2)0.2368 (5)0.51164 (17)0.0242 (10)
H6B0.40340.19330.52280.030*
C7B0.36814 (19)−0.0772 (5)0.51006 (17)0.0190 (9)
C8B0.3884 (2)−0.1814 (5)0.54805 (17)0.0225 (10)
C9B0.4402 (2)−0.2628 (5)0.55191 (19)0.0257 (11)
H9B0.4519−0.33300.57860.032*
C10B0.4748 (2)−0.2417 (5)0.51689 (19)0.0268 (11)
H10B0.5116−0.29370.52040.033*
C11B0.4556 (2)−0.1444 (5)0.47657 (18)0.0252 (11)
H11B0.4784−0.13120.45140.031*
C12B0.4025 (2)−0.0658 (5)0.47319 (17)0.0214 (10)
C13B0.1965 (2)0.1273 (6)0.47323 (19)0.0301 (11)
H13B0.20310.03910.45480.038*
H14B0.16310.18180.44950.038*
C14B0.1778 (2)0.0877 (6)0.5227 (2)0.0328 (12)
Cl1C0.16720 (6)0.69718 (13)0.42201 (5)0.0336 (3)
Cl2C0.21473 (5)0.43552 (12)0.25345 (4)0.0255 (3)
O1C0.04580 (15)0.4563 (4)0.38634 (14)0.0411 (10)
O2C−0.04894 (17)0.3889 (5)0.35016 (16)0.0530 (12)
N1C0.14390 (16)0.4798 (4)0.33667 (15)0.0232 (9)
H1C0.10980.52530.33610.029*
C1C0.1419 (2)0.3294 (5)0.33264 (17)0.0217 (10)
C2C0.0844 (2)0.2630 (5)0.31616 (17)0.0253 (11)
C3C0.0826 (2)0.1146 (5)0.31193 (19)0.0313 (12)
H3C0.04420.06810.30090.039*
C4C0.1358 (3)0.0334 (5)0.3235 (2)0.0356 (13)
H4C0.1336−0.06750.31980.045*
C5C0.1915 (2)0.1004 (5)0.34023 (19)0.0313 (12)
H5C0.22790.04530.34840.039*
C6C0.1949 (2)0.2459 (5)0.34527 (18)0.0256 (11)
H6C0.23370.29050.35740.032*
C7C0.19673 (19)0.5604 (5)0.34152 (17)0.0205 (10)
C8C0.2140 (2)0.6671 (5)0.37992 (17)0.0221 (10)
C9C0.2652 (2)0.7500 (5)0.38571 (19)0.0272 (11)
H9C0.27490.82080.41230.034*
C10C0.3024 (2)0.7299 (5)0.35265 (19)0.0259 (11)
H10C0.33890.78380.35730.032*
C11C0.2863 (2)0.6310 (5)0.31280 (18)0.0238 (10)
H11C0.31120.61870.28930.030*
C12C0.23409 (19)0.5495 (5)0.30694 (17)0.0201 (10)
C13C0.0258 (2)0.3476 (6)0.30202 (18)0.0285 (11)
H13C−0.00710.28720.28030.036*
H14C0.03110.43080.28060.036*
C14C0.0061 (2)0.4000 (5)0.3497 (2)0.0308 (12)
Cl1D0.00610 (6)−0.21160 (14)0.25532 (5)0.0366 (3)
Cl2D0.05621 (5)0.04400 (12)0.08711 (4)0.0276 (3)
O1D−0.11495 (18)0.0437 (6)0.21934 (16)0.0627 (14)
O2D−0.1769 (2)0.2278 (7)0.20130 (17)0.0850 (18)
N1D−0.01196 (17)0.0122 (4)0.17183 (15)0.0268 (9)
H1D−0.0467−0.02820.17270.034*
C1D−0.0109 (2)0.1624 (5)0.16630 (17)0.0222 (10)
C2D−0.0659 (2)0.2348 (5)0.14770 (17)0.0258 (11)
C3D−0.0644 (2)0.3829 (6)0.14207 (19)0.0333 (12)
H3D−0.10170.43340.12970.042*
C4D−0.0101 (2)0.4577 (5)0.15402 (19)0.0345 (12)
H4D−0.01010.55800.14890.043*
C5D0.0442 (2)0.3854 (5)0.17354 (18)0.0284 (11)
H5D0.08180.43600.18270.035*
C6D0.0435 (2)0.2384 (5)0.17967 (17)0.0245 (10)
H6D0.08090.18900.19320.031*
C7D0.0387 (2)−0.0754 (5)0.17599 (17)0.0226 (10)
C8D0.0539 (2)−0.1828 (5)0.21421 (18)0.0257 (10)
C9D0.1045 (2)−0.2686 (5)0.21988 (19)0.0291 (11)
H9D0.1134−0.33950.24650.036*
C10D0.1422 (2)−0.2516 (5)0.18698 (19)0.0289 (11)
H10D0.1780−0.30790.19160.036*
C11D0.1271 (2)−0.1516 (5)0.14716 (19)0.0284 (11)
H11D0.1523−0.14000.12380.036*
C12D0.0756 (2)−0.0688 (5)0.14144 (17)0.0220 (10)
C13D−0.1259 (2)0.1571 (6)0.13707 (18)0.0314 (12)
H13D−0.12260.06310.12090.039*
H14D−0.15820.21290.11260.039*
C14D−0.1417 (2)0.1374 (8)0.1894 (2)0.0531 (18)
O10.43163 (19)0.8630 (5)0.01263 (16)0.0581 (12)
H110.43820.89010.04300.073*
H120.41470.78760.00180.073*
O20.6611 (3)0.3245 (6)0.2346 (2)0.104 (2)
H210.66340.25500.25820.130*
H220.64690.38980.24880.130*
O30.6455 (15)0.037 (4)0.2712 (11)0.068 (9)0.20
O40.6351 (5)0.0291 (12)0.2458 (4)0.061 (3)0.50
O50.2808 (9)0.063 (2)0.6661 (7)0.074 (5)0.30
O60.2433 (10)0.048 (2)0.6627 (8)0.082 (6)0.30
O70.5885 (3)0.4749 (8)0.1084 (3)0.0510 (17)0.70
O80.5884 (14)0.398 (3)0.1120 (12)0.071 (9)0.20
O90.5281 (7)0.4246 (18)0.1127 (7)0.072 (5)0.30
O100.4590 (5)0.4878 (12)0.0794 (4)0.071 (3)0.50
O110.5006 (4)0.1877 (10)0.0722 (4)0.057 (2)0.50
O120.5137 (7)0.2597 (18)0.1046 (7)0.065 (4)0.30
O130.4813 (10)0.530 (3)0.0674 (10)0.055 (6)0.20
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
N1A0.056 (3)0.104 (5)0.041 (3)−0.002 (3)0.023 (3)−0.028 (3)
C2A0.046 (3)0.078 (5)0.038 (3)0.007 (3)0.020 (3)0.000 (3)
C3A0.038 (3)0.106 (6)0.037 (3)0.000 (4)0.018 (3)−0.013 (4)
N4A0.039 (3)0.093 (4)0.043 (3)0.009 (3)0.010 (2)0.015 (3)
C5A0.051 (4)0.185 (11)0.065 (5)0.001 (6)0.016 (4)−0.035 (6)
C6A0.033 (4)0.083 (6)0.138 (8)−0.002 (4)0.005 (4)0.031 (6)
N71A0.053 (5)0.109 (8)0.069 (6)0.026 (5)0.011 (4)0.000 (6)
N72A0.076 (13)0.081 (14)0.059 (12)−0.044 (11)0.046 (10)−0.031 (11)
C8A0.066 (4)0.105 (4)0.062 (4)0.027 (3)0.023 (3)0.002 (3)
C9A0.083 (4)0.114 (5)0.073 (4)0.019 (4)0.037 (3)0.003 (4)
N10A0.095 (5)0.114 (5)0.040 (3)0.068 (4)0.027 (3)0.025 (3)
Cl1B0.0393 (7)0.0315 (7)0.0340 (7)0.0003 (6)0.0182 (6)0.0088 (6)
Cl2B0.0356 (6)0.0245 (6)0.0202 (6)0.0025 (5)0.0091 (5)0.0039 (5)
O1B0.037 (2)0.108 (4)0.031 (2)−0.007 (2)0.0107 (18)0.023 (2)
O2B0.072 (3)0.095 (4)0.114 (4)0.047 (3)0.073 (3)0.063 (3)
N1B0.0194 (19)0.020 (2)0.035 (2)−0.0013 (16)0.0102 (17)0.0046 (18)
C1B0.032 (3)0.024 (3)0.015 (2)−0.001 (2)0.010 (2)−0.0001 (19)
C2B0.031 (3)0.029 (3)0.019 (2)0.004 (2)0.008 (2)0.005 (2)
C3B0.040 (3)0.029 (3)0.028 (3)0.017 (2)0.011 (2)0.006 (2)
C4B0.058 (4)0.020 (3)0.033 (3)0.003 (3)0.015 (3)0.001 (2)
C5B0.045 (3)0.026 (3)0.025 (3)−0.008 (2)0.017 (2)−0.005 (2)
C6B0.029 (3)0.025 (3)0.019 (2)−0.001 (2)0.008 (2)−0.002 (2)
C7B0.020 (2)0.015 (2)0.021 (2)−0.0032 (18)0.0051 (18)−0.0045 (19)
C8B0.025 (2)0.022 (2)0.022 (2)−0.004 (2)0.0078 (19)0.002 (2)
C9B0.030 (3)0.019 (2)0.025 (3)−0.002 (2)0.002 (2)0.000 (2)
C10B0.023 (2)0.023 (3)0.032 (3)0.003 (2)0.003 (2)−0.002 (2)
C11B0.025 (2)0.023 (3)0.028 (3)−0.004 (2)0.007 (2)−0.005 (2)
C12B0.026 (2)0.017 (2)0.018 (2)−0.0043 (19)0.0003 (18)−0.0011 (19)
C13B0.021 (2)0.042 (3)0.028 (3)0.005 (2)0.007 (2)0.005 (2)
C14B0.034 (3)0.033 (3)0.037 (3)0.000 (2)0.020 (2)0.001 (2)
Cl1C0.0436 (7)0.0301 (7)0.0331 (7)−0.0001 (6)0.0204 (6)−0.0058 (6)
Cl2C0.0309 (6)0.0240 (6)0.0225 (6)0.0003 (5)0.0086 (5)−0.0030 (5)
O1C0.0301 (19)0.060 (3)0.034 (2)−0.0071 (18)0.0114 (16)−0.022 (2)
O2C0.037 (2)0.079 (3)0.052 (3)−0.027 (2)0.0299 (19)−0.031 (2)
N1C0.0205 (19)0.020 (2)0.030 (2)0.0015 (16)0.0094 (16)0.0007 (17)
C1C0.029 (2)0.018 (2)0.020 (2)−0.001 (2)0.011 (2)0.0006 (19)
C2C0.033 (3)0.028 (3)0.018 (2)−0.003 (2)0.011 (2)−0.007 (2)
C3C0.041 (3)0.028 (3)0.028 (3)−0.012 (2)0.014 (2)−0.005 (2)
C4C0.058 (4)0.019 (3)0.032 (3)−0.002 (3)0.015 (3)−0.002 (2)
C5C0.044 (3)0.023 (3)0.029 (3)0.010 (2)0.014 (2)0.008 (2)
C6C0.030 (3)0.026 (3)0.024 (3)0.001 (2)0.013 (2)0.005 (2)
C7C0.022 (2)0.016 (2)0.023 (2)0.0053 (19)0.0049 (19)0.0048 (19)
C8C0.027 (2)0.020 (2)0.019 (2)0.007 (2)0.0068 (19)0.004 (2)
C9C0.032 (3)0.020 (2)0.026 (3)0.000 (2)0.000 (2)0.001 (2)
C10C0.023 (2)0.020 (2)0.033 (3)−0.001 (2)0.005 (2)0.003 (2)
C11C0.027 (2)0.020 (2)0.025 (3)0.005 (2)0.008 (2)0.007 (2)
C12C0.023 (2)0.016 (2)0.019 (2)0.0041 (19)0.0019 (18)0.0023 (18)
C13C0.026 (2)0.039 (3)0.022 (3)−0.004 (2)0.008 (2)−0.005 (2)
C14C0.031 (3)0.035 (3)0.032 (3)−0.006 (2)0.018 (2)−0.001 (2)
Cl1D0.0487 (8)0.0305 (7)0.0332 (7)−0.0067 (6)0.0152 (6)0.0045 (6)
Cl2D0.0360 (6)0.0248 (6)0.0225 (6)−0.0009 (5)0.0088 (5)0.0007 (5)
O1D0.037 (2)0.113 (4)0.042 (2)0.013 (2)0.0165 (19)0.035 (3)
O2D0.052 (3)0.169 (5)0.037 (2)0.044 (3)0.016 (2)−0.001 (3)
N1D0.025 (2)0.025 (2)0.030 (2)0.0000 (17)0.0069 (18)0.0034 (18)
C1D0.031 (3)0.022 (2)0.014 (2)0.005 (2)0.0070 (19)−0.0004 (19)
C2D0.029 (3)0.033 (3)0.015 (2)0.009 (2)0.0051 (19)−0.002 (2)
C3D0.040 (3)0.037 (3)0.019 (3)0.014 (2)0.002 (2)0.002 (2)
C4D0.052 (3)0.025 (3)0.026 (3)0.009 (3)0.010 (2)0.002 (2)
C5D0.040 (3)0.026 (3)0.021 (3)0.000 (2)0.011 (2)−0.002 (2)
C6D0.029 (3)0.024 (3)0.019 (2)0.002 (2)0.005 (2)−0.002 (2)
C7D0.022 (2)0.020 (2)0.021 (2)−0.0056 (19)−0.0019 (19)−0.003 (2)
C8D0.031 (3)0.020 (2)0.023 (3)−0.007 (2)0.003 (2)−0.003 (2)
C9D0.038 (3)0.017 (2)0.027 (3)−0.003 (2)−0.002 (2)0.001 (2)
C10D0.031 (3)0.019 (3)0.031 (3)0.004 (2)−0.001 (2)−0.005 (2)
C11D0.030 (3)0.021 (3)0.035 (3)−0.005 (2)0.009 (2)−0.010 (2)
C12D0.030 (2)0.014 (2)0.020 (2)−0.0047 (19)0.0019 (19)−0.0013 (18)
C13D0.026 (3)0.046 (3)0.021 (3)0.002 (2)0.003 (2)0.004 (2)
C14D0.024 (3)0.107 (6)0.026 (3)0.009 (3)0.001 (2)0.005 (3)
O10.064 (2)0.065 (3)0.041 (2)−0.026 (2)0.0055 (19)−0.003 (2)
O20.129 (4)0.091 (3)0.092 (4)0.017 (3)0.030 (3)−0.018 (3)
O30.081 (12)0.070 (12)0.051 (12)−0.019 (9)0.017 (9)0.005 (9)
O40.062 (5)0.053 (5)0.052 (6)0.007 (4)−0.011 (5)0.007 (5)
O50.086 (9)0.074 (9)0.063 (8)−0.005 (8)0.020 (8)0.001 (7)
O60.088 (9)0.085 (10)0.071 (9)0.004 (8)0.018 (8)0.003 (7)
O70.047 (3)0.059 (4)0.057 (3)0.002 (3)0.032 (3)−0.003 (3)
O80.068 (10)0.077 (10)0.071 (10)0.003 (5)0.024 (5)−0.005 (5)
O90.070 (6)0.071 (6)0.075 (6)0.001 (5)0.020 (5)0.003 (5)
O100.074 (5)0.074 (5)0.063 (5)0.010 (4)0.016 (4)0.006 (4)
O110.056 (5)0.062 (5)0.053 (5)−0.008 (4)0.015 (4)0.018 (4)
O120.064 (6)0.062 (6)0.072 (6)0.003 (4)0.022 (5)0.005 (5)
O130.048 (7)0.058 (8)0.060 (8)−0.004 (5)0.016 (5)0.004 (5)
Geometric parameters (Å, º) top
N1A—C5A1.433 (10)N1C—H1C0.88
N1A—C2A1.465 (7)C1C—C6C1.401 (6)
N1A—C8A1.523 (9)C1C—C2C1.405 (6)
C2A—C3A1.491 (8)C2C—C3C1.395 (7)
C2A—H21A0.99C2C—C13C1.509 (7)
C2A—H22A0.99C3C—C4C1.391 (7)
C3A—N4A1.505 (8)C3C—H3C0.95
C3A—H31A0.99C4C—C5C1.377 (7)
C3A—H32A0.99C4C—H4C0.95
N4A—H41A0.91C5C—C6C1.370 (7)
N4A—H42A0.91C5C—H5C0.95
N4A—H43A0.91C6C—H6C0.95
C5A—C6A1.547 (12)C7C—C12C1.403 (6)
C5A—H51A0.99C7C—C8C1.405 (6)
C5A—H52A0.99C8C—C9C1.372 (6)
C6A—N72A1.543 (16)C9C—C10C1.377 (7)
C6A—N71A1.543 (12)C9C—H9C0.95
N71A—H71A0.91C10C—C11C1.378 (6)
N71A—H72A0.91C10C—H10C0.95
N71A—H73A0.91C11C—C12C1.384 (6)
N72A—H74A0.91C11C—H11C0.95
N72A—H75A0.91C13C—C14C1.524 (6)
N72A—H76A0.91C13C—H13C0.99
C8A—C9A1.500 (10)C13C—H14C0.99
C8A—H81A0.99Cl1D—C8D1.745 (5)
C8A—H82A0.99Cl2D—C12D1.744 (4)
C9A—N10A1.527 (10)O1D—C14D1.231 (7)
C9A—H91A0.99O2D—C14D1.258 (8)
C9A—H92A0.99N1D—C7D1.393 (6)
N10A—H11A0.91N1D—C1D1.417 (6)
N10A—H12A0.91N1D—H1D0.88
N10A—H13A0.91C1D—C6D1.387 (6)
Cl1B—C8B1.754 (4)C1D—C2D1.392 (6)
Cl2B—C12B1.741 (4)C2D—C3D1.397 (7)
O1B—C14B1.226 (6)C2D—C13D1.504 (7)
O2B—C14B1.256 (6)C3D—C4D1.379 (7)
N1B—C7B1.391 (5)C3D—H3D0.95
N1B—C1B1.431 (6)C4D—C5D1.381 (7)
N1B—H1B0.88C4D—H4D0.95
C1B—C6B1.393 (6)C5D—C6D1.388 (7)
C1B—C2B1.396 (6)C5D—H5D0.95
C2B—C3B1.396 (7)C6D—H6D0.95
C2B—C13B1.506 (7)C7D—C12D1.392 (6)
C3B—C4B1.381 (7)C7D—C8D1.403 (6)
C3B—H3B0.95C8D—C9D1.376 (7)
C4B—C5B1.384 (7)C9D—C10D1.378 (7)
C4B—H4B0.95C9D—H9D0.95
C5B—C6B1.386 (7)C10D—C11D1.383 (7)
C5B—H5B0.95C10D—H10D0.95
C6B—H6B0.95C11D—C12D1.377 (6)
C7B—C8B1.389 (6)C11D—H11D0.95
C7B—C12B1.401 (6)C13D—C14D1.527 (7)
C8B—C9B1.382 (6)C13D—H13D0.99
C9B—C10B1.374 (7)C13D—H14D0.99
C9B—H9B0.95O1—H110.817 (4)
C10B—C11B1.383 (7)O1—H120.820 (4)
C10B—H10B0.95O2—H210.894 (6)
C11B—C12B1.395 (6)O2—H220.826 (5)
C11B—H11B0.95O3—O40.65 (3)
C13B—C14B1.523 (7)O5—O60.84 (2)
C13B—H13B0.99O7—O80.72 (3)
C13B—H14B0.99O7—O91.480 (17)
Cl1C—C8C1.749 (4)O8—O91.40 (3)
Cl2C—C12C1.733 (4)O9—O101.691 (19)
O1C—C14C1.253 (6)O9—O131.69 (3)
O2C—C14C1.255 (6)O9—O121.58 (2)
N1C—C7C1.393 (6)O10—O130.77 (2)
N1C—C1C1.414 (6)O11—O121.069 (17)
C5A—N1A—C2A116.5 (6)C14B—C13B—H14B109.3
C5A—N1A—C8A108.2 (6)H13B—C13B—H14B108.0
C2A—N1A—C8A108.5 (5)O1B—C14B—O2B122.9 (5)
N1A—C2A—C3A111.1 (5)O1B—C14B—C13B119.4 (4)
N1A—C2A—H21A109.4O2B—C14B—C13B117.6 (5)
C3A—C2A—H21A109.4C7C—N1C—C1C123.9 (4)
N1A—C2A—H22A109.4C7C—N1C—H1C118.1
C3A—C2A—H22A109.4C1C—N1C—H1C118.1
H21A—C2A—H22A108.0C6C—C1C—C2C119.7 (4)
C2A—C3A—N4A108.7 (6)C6C—C1C—N1C122.0 (4)
C2A—C3A—H31A110.0C2C—C1C—N1C118.3 (4)
N4A—C3A—H31A110.0C3C—C2C—C1C118.1 (5)
C2A—C3A—H32A110.0C3C—C2C—C13C119.8 (4)
N4A—C3A—H32A110.0C1C—C2C—C13C122.0 (4)
H31A—C3A—H32A108.3C4C—C3C—C2C121.5 (5)
C3A—N4A—H41A109.5C4C—C3C—H3C119.2
C3A—N4A—H42A109.5C2C—C3C—H3C119.2
H41A—N4A—H42A109.5C5C—C4C—C3C119.4 (5)
C3A—N4A—H43A109.5C5C—C4C—H4C120.3
H41A—N4A—H43A109.5C3C—C4C—H4C120.3
H42A—N4A—H43A109.5C6C—C5C—C4C120.6 (5)
N1A—C5A—C6A109.2 (6)C6C—C5C—H5C119.7
N1A—C5A—H51A109.8C4C—C5C—H5C119.7
C6A—C5A—H51A109.8C5C—C6C—C1C120.6 (5)
N1A—C5A—H52A109.8C5C—C6C—H6C119.7
C6A—C5A—H52A109.8C1C—C6C—H6C119.7
H51A—C5A—H52A108.3N1C—C7C—C12C123.5 (4)
N72A—C6A—N71A103.6 (9)N1C—C7C—C8C121.5 (4)
N72A—C6A—C5A114.2 (10)C12C—C7C—C8C114.8 (4)
N71A—C6A—C5A115.4 (6)C9C—C8C—C7C123.5 (4)
C6A—N71A—H71A109.5C9C—C8C—Cl1C118.3 (4)
C6A—N71A—H72A109.5C7C—C8C—Cl1C118.2 (3)
H71A—N71A—H72A109.5C8C—C9C—C10C119.5 (4)
C6A—N71A—H73A109.5C8C—C9C—H9C120.2
H71A—N71A—H73A109.5C10C—C9C—H9C120.2
H72A—N71A—H73A109.5C9C—C10C—C11C119.5 (4)
C6A—N72A—H74A109.5C9C—C10C—H10C120.2
C6A—N72A—H75A109.5C11C—C10C—H10C120.2
H74A—N72A—H75A109.5C10C—C11C—C12C120.3 (4)
C6A—N72A—H76A109.5C10C—C11C—H11C119.8
H74A—N72A—H76A109.5C12C—C11C—H11C119.8
H75A—N72A—H76A109.5C11C—C12C—C7C122.2 (4)
C9A—C8A—N1A113.6 (6)C11C—C12C—Cl2C117.3 (3)
C9A—C8A—H81A108.8C7C—C12C—Cl2C120.6 (3)
N1A—C8A—H81A108.8C2C—C13C—C14C113.2 (4)
C9A—C8A—H82A108.8C2C—C13C—H13C108.9
N1A—C8A—H82A108.8C14C—C13C—H13C108.9
H81A—C8A—H82A107.7C2C—C13C—H14C108.9
N10A—C9A—C8A111.4 (7)C14C—C13C—H14C108.9
N10A—C9A—H91A109.3H13C—C13C—H14C107.7
C8A—C9A—H91A109.3O1C—C14C—O2C122.9 (4)
N10A—C9A—H92A109.3O1C—C14C—C13C117.8 (4)
C8A—C9A—H92A109.3O2C—C14C—C13C119.2 (4)
H91A—C9A—H92A108.0C7D—N1D—C1D123.9 (4)
C9A—N10A—H11A109.5C7D—N1D—H1D118.0
C9A—N10A—H12A109.5C1D—N1D—H1D118.0
H11A—N10A—H12A109.5C6D—C1D—C2D119.6 (4)
C9A—N10A—H13A109.5C6D—C1D—N1D121.5 (4)
H11A—N10A—H13A109.5C2D—C1D—N1D118.8 (4)
H12A—N10A—H13A109.5C1D—C2D—C3D118.5 (5)
C7B—N1B—C1B123.5 (4)C1D—C2D—C13D120.9 (4)
C7B—N1B—H1B118.3C3D—C2D—C13D120.5 (4)
C1B—N1B—H1B118.3C4D—C3D—C2D121.8 (5)
C6B—C1B—C2B120.5 (4)C4D—C3D—H3D119.1
C6B—C1B—N1B121.4 (4)C2D—C3D—H3D119.1
C2B—C1B—N1B118.0 (4)C3D—C4D—C5D119.3 (5)
C1B—C2B—C3B117.8 (5)C3D—C4D—H4D120.3
C1B—C2B—C13B121.8 (4)C5D—C4D—H4D120.3
C3B—C2B—C13B120.4 (4)C4D—C5D—C6D119.7 (5)
C4B—C3B—C2B122.1 (5)C4D—C5D—H5D120.2
C4B—C3B—H3B118.9C6D—C5D—H5D120.2
C2B—C3B—H3B118.9C5D—C6D—C1D121.1 (5)
C3B—C4B—C5B119.2 (5)C5D—C6D—H6D119.5
C3B—C4B—H4B120.4C1D—C6D—H6D119.5
C5B—C4B—H4B120.4C12D—C7D—N1D123.2 (4)
C4B—C5B—C6B120.1 (5)C12D—C7D—C8D115.3 (4)
C4B—C5B—H5B119.9N1D—C7D—C8D121.5 (4)
C6B—C5B—H5B119.9C9D—C8D—C7D122.6 (4)
C5B—C6B—C1B120.2 (5)C9D—C8D—Cl1D118.5 (4)
C5B—C6B—H6B119.9C7D—C8D—Cl1D118.9 (4)
C1B—C6B—H6B119.9C8D—C9D—C10D120.0 (5)
N1B—C7B—C8B122.0 (4)C8D—C9D—H9D120.0
N1B—C7B—C12B123.2 (4)C10D—C9D—H9D120.0
C8B—C7B—C12B114.6 (4)C9D—C10D—C11D119.2 (4)
C9B—C8B—C7B123.8 (4)C9D—C10D—H10D120.4
C9B—C8B—Cl1B117.7 (4)C11D—C10D—H10D120.4
C7B—C8B—Cl1B118.6 (3)C12D—C11D—C10D119.9 (5)
C10B—C9B—C8B119.6 (4)C12D—C11D—H11D120.0
C10B—C9B—H9B120.2C10D—C11D—H11D120.0
C8B—C9B—H9B120.2C11D—C12D—C7D122.8 (4)
C9B—C10B—C11B119.5 (4)C11D—C12D—Cl2D117.1 (4)
C9B—C10B—H10B120.2C7D—C12D—Cl2D120.1 (3)
C11B—C10B—H10B120.2C2D—C13D—C14D107.8 (4)
C10B—C11B—C12B119.3 (4)C2D—C13D—H13D110.2
C10B—C11B—H11B120.3C14D—C13D—H13D110.2
C12B—C11B—H11B120.3C2D—C13D—H14D110.2
C11B—C12B—C7B122.9 (4)C14D—C13D—H14D110.2
C11B—C12B—Cl2B116.8 (3)H13D—C13D—H14D108.5
C7B—C12B—Cl2B120.3 (3)O1D—C14D—O2D123.9 (6)
C2B—C13B—C14B111.7 (4)O1D—C14D—C13D118.4 (5)
C2B—C13B—H13B109.3O2D—C14D—C13D117.3 (6)
C14B—C13B—H13B109.3H11—O1—H12124.0 (5)
C2B—C13B—H14B109.3H21—O2—H22100.5 (7)
C5A—N1A—C2A—C3A−148.4 (6)N1C—C1C—C6C—C5C−179.1 (4)
C8A—N1A—C2A—C3A89.3 (7)C1C—N1C—C7C—C12C53.0 (6)
N1A—C2A—C3A—N4A63.5 (7)C1C—N1C—C7C—C8C−131.6 (5)
C2A—N1A—C5A—C6A78.9 (8)N1C—C7C—C8C—C9C−179.2 (4)
C8A—N1A—C5A—C6A−158.7 (6)C12C—C7C—C8C—C9C−3.5 (6)
N1A—C5A—C6A—N72A60.8 (11)N1C—C7C—C8C—Cl1C0.0 (6)
N1A—C5A—C6A—N71A−179.3 (7)C12C—C7C—C8C—Cl1C175.7 (3)
C5A—N1A—C8A—C9A84.6 (8)C7C—C8C—C9C—C10C0.0 (7)
C2A—N1A—C8A—C9A−148.2 (7)Cl1C—C8C—C9C—C10C−179.2 (4)
N1A—C8A—C9A—N10A64.6 (9)C8C—C9C—C10C—C11C2.8 (7)
C7B—N1B—C1B—C6B−16.9 (7)C9C—C10C—C11C—C12C−1.9 (7)
C7B—N1B—C1B—C2B164.1 (4)C10C—C11C—C12C—C7C−1.9 (7)
C6B—C1B—C2B—C3B1.1 (7)C10C—C11C—C12C—Cl2C176.2 (3)
N1B—C1B—C2B—C3B−180.0 (4)N1C—C7C—C12C—C11C−180.0 (4)
C6B—C1B—C2B—C13B179.1 (4)C8C—C7C—C12C—C11C4.4 (6)
N1B—C1B—C2B—C13B−1.9 (6)N1C—C7C—C12C—Cl2C2.0 (6)
C1B—C2B—C3B—C4B−0.1 (7)C8C—C7C—C12C—Cl2C−173.6 (3)
C13B—C2B—C3B—C4B−178.2 (4)C3C—C2C—C13C—C14C103.2 (5)
C2B—C3B—C4B—C5B−0.9 (8)C1C—C2C—C13C—C14C−78.2 (6)
C3B—C4B—C5B—C6B0.9 (7)C2C—C13C—C14C—O1C46.1 (6)
C4B—C5B—C6B—C1B0.0 (7)C2C—C13C—C14C—O2C−135.9 (5)
C2B—C1B—C6B—C5B−1.0 (7)C7D—N1D—C1D—C6D−19.1 (7)
N1B—C1B—C6B—C5B−180.0 (4)C7D—N1D—C1D—C2D161.8 (4)
C1B—N1B—C7B—C8B133.0 (5)C6D—C1D—C2D—C3D1.3 (7)
C1B—N1B—C7B—C12B−52.0 (6)N1D—C1D—C2D—C3D−179.6 (4)
N1B—C7B—C8B—C9B179.0 (4)C6D—C1D—C2D—C13D−174.9 (4)
C12B—C7B—C8B—C9B3.7 (6)N1D—C1D—C2D—C13D4.1 (6)
N1B—C7B—C8B—Cl1B−0.7 (6)C1D—C2D—C3D—C4D0.5 (7)
C12B—C7B—C8B—Cl1B−176.0 (3)C13D—C2D—C3D—C4D176.8 (4)
C7B—C8B—C9B—C10B0.3 (7)C2D—C3D—C4D—C5D−1.9 (8)
Cl1B—C8B—C9B—C10B180.0 (4)C3D—C4D—C5D—C6D1.5 (7)
C8B—C9B—C10B—C11B−3.3 (7)C4D—C5D—C6D—C1D0.3 (7)
C9B—C10B—C11B—C12B2.1 (7)C2D—C1D—C6D—C5D−1.7 (7)
C10B—C11B—C12B—C7B2.2 (7)N1D—C1D—C6D—C5D179.3 (4)
C10B—C11B—C12B—Cl2B−175.6 (3)C1D—N1D—C7D—C12D−50.0 (6)
N1B—C7B—C12B—C11B179.8 (4)C1D—N1D—C7D—C8D133.6 (5)
C8B—C7B—C12B—C11B−4.9 (6)C12D—C7D—C8D—C9D4.8 (6)
N1B—C7B—C12B—Cl2B−2.5 (6)N1D—C7D—C8D—C9D−178.5 (4)
C8B—C7B—C12B—Cl2B172.9 (3)C12D—C7D—C8D—Cl1D−173.8 (3)
C1B—C2B—C13B—C14B82.7 (6)N1D—C7D—C8D—Cl1D2.9 (6)
C3B—C2B—C13B—C14B−99.4 (5)C7D—C8D—C9D—C10D−0.6 (7)
C2B—C13B—C14B—O1B−52.8 (7)Cl1D—C8D—C9D—C10D178.0 (4)
C2B—C13B—C14B—O2B127.6 (6)C8D—C9D—C10D—C11D−2.5 (7)
C7C—N1C—C1C—C6C15.2 (7)C9D—C10D—C11D—C12D1.2 (7)
C7C—N1C—C1C—C2C−165.8 (4)C10D—C11D—C12D—C7D3.5 (7)
C6C—C1C—C2C—C3C−1.3 (7)C10D—C11D—C12D—Cl2D−174.7 (3)
N1C—C1C—C2C—C3C179.6 (4)N1D—C7D—C12D—C11D177.1 (4)
C6C—C1C—C2C—C13C−180.0 (4)C8D—C7D—C12D—C11D−6.2 (6)
N1C—C1C—C2C—C13C1.0 (6)N1D—C7D—C12D—Cl2D−4.7 (6)
C1C—C2C—C3C—C4C−0.1 (7)C8D—C7D—C12D—Cl2D171.9 (3)
C13C—C2C—C3C—C4C178.5 (4)C1D—C2D—C13D—C14D80.6 (6)
C2C—C3C—C4C—C5C1.0 (8)C3D—C2D—C13D—C14D−95.6 (6)
C3C—C4C—C5C—C6C−0.4 (8)C2D—C13D—C14D—O1D−77.0 (7)
C4C—C5C—C6C—C1C−1.0 (7)C2D—C13D—C14D—O2D96.0 (6)
C2C—C1C—C6C—C5C1.9 (7)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N4A—H41A···O2Ci0.911.992.841 (6)156
N4A—H42A···O10.912.052.845 (6)145
N4A—H43A···O1ii0.911.972.876 (7)174
N71A—H71A···O2Diii0.911.802.692 (9)166
N71A—H72A···O2iv0.911.902.785 (10)163
N71A—H73A···O1Bv0.912.132.999 (11)161
N72A—H74A···O2Ci0.911.902.758 (17)156
N72A—H75A···O8iv0.912.002.79 (4)145
N72A—H75A···O12iv0.911.952.75 (3)146
N72A—H75A···O11iv0.912.443.06 (2)125
N72A—H75A···O9iv0.912.603.50 (3)177
N72A—H76A···O4iv0.911.792.57 (2)141
N72A—H76A···O2iv0.912.192.816 (18)125
N72A—H76A···O3iv0.912.323.15 (3)152
N10A—H11A···O2Ci0.911.922.816 (6)169
N10A—H12A···O1Di0.912.032.932 (7)172
N10A—H12A···O2Di0.912.302.935 (7)126
N10A—H13A···O70.911.862.751 (10)167
N10A—H13A···O80.912.343.23 (3)167
N1B—H1B···O1B0.882.372.961 (5)124
N1C—H1C···O1C0.882.302.872 (5)123
N1D—H1D···O1D0.882.322.941 (5)128
O1—H11···O1Ci0.82 (1)1.91 (1)2.726 (6)179 (3)
O1—H12···O2Bi0.82 (1)1.88 (1)2.698 (6)179 (3)
O2—H21···O30.89 (1)2.13 (3)2.92 (3)146 (3)
O2—H21···O40.89 (1)2.21 (1)2.863 (13)129 (3)
O2—H22···O1Di0.83 (1)1.91 (1)2.732 (7)179 (3)
Symmetry codes: (i) −x+1/2, y+1/2, −z+1/2; (ii) −x+1, −y+2, −z; (iii) x+1, y+1, z; (iv) x, y+1, z; (v) x+1/2, −y+3/2, z−1/2.

Experimental details

Crystal data
Chemical formulaC6H21N43+·3C14H10Cl2NO2−·6H2O
Mr1142.75
Crystal system, space groupMonoclinic, P21/n
Temperature (K)150
a, b, c (Å)22.677 (4), 9.3735 (17), 26.415 (5)
β (°) 105.176 (17)
V (Å3)5419.0 (18)
Z4
Radiation typeMo Kα
µ (mm−1)0.38
Crystal size (mm)0.77 × 0.58 × 0.31
Data collection
DiffractometerStoe Stadi-4
diffractometer
Absorption correctionψ scan
(Stoe & Cie, 1995)
Tmin, Tmax0.757, 0.891
No. of measured, independent and
observed [I > 2σ(I)] reflections		9857, 9532, 5678
Rint0.025
(sin θ/λ)max (Å−1)0.595
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.070, 0.222, 1.02
No. of reflections9532
No. of parameters734
No. of restraints100
H-atom treatmentH atoms treated by a mixture of independent and constrained refinement
Δρmax, Δρmin (e Å−3)0.70, −0.50

Computer programs: DIF4 (Stoe & Cie, 1990), DIF4, REDU4 (Stoe & Cie, 1990), SHELXS97 (Sheldrick, 1997), SHELXL97 (Sheldrick, 1997), PLATON97 (Spek, 1997), SHELXL97.

Selected bond lengths (Å) top
O3—O40.65 (3)O9—O101.691 (19)
O5—O60.84 (2)O9—O131.69 (3)
O7—O80.72 (3)O9—O121.58 (2)
O7—O91.480 (17)O10—O130.77 (2)
O8—O91.40 (3)O11—O121.069 (17)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N4A—H41A···O2Ci0.911.992.841 (6)156
N4A—H42A···O10.912.052.845 (6)145
N4A—H43A···O1ii0.911.972.876 (7)174
N71A—H71A···O2Diii0.911.802.692 (9)166
N71A—H72A···O2iv0.911.902.785 (10)163
N71A—H73A···O1Bv0.912.132.999 (11)161
N72A—H74A···O2Ci0.911.902.758 (17)156
N72A—H75A···O8iv0.912.002.79 (4)145
N72A—H75A···O12iv0.911.952.75 (3)146
N72A—H75A···O11iv0.912.443.06 (2)125
N72A—H75A···O9iv0.912.603.50 (3)177
N72A—H76A···O4iv0.911.792.57 (2)141
N72A—H76A···O2iv0.912.192.816 (18)125
N72A—H76A···O3iv0.912.323.15 (3)152
N10A—H11A···O2Ci0.911.922.816 (6)169
N10A—H12A···O1Di0.912.032.932 (7)172
N10A—H12A···O2Di0.912.302.935 (7)126
N10A—H13A···O70.911.862.751 (10)167
N10A—H13A···O80.912.343.23 (3)167
N1B—H1B···O1B0.882.372.961 (5)124
N1C—H1C···O1C0.882.302.872 (5)123
N1D—H1D···O1D0.882.322.941 (5)128
O1—H11···O1Ci0.817 (4)1.909 (4)2.726 (6)179 (3)
O1—H12···O2Bi0.820 (4)1.878 (4)2.698 (6)179 (3)
O2—H21···O30.894 (6)2.13 (3)2.92 (3)146 (3)
O2—H21···O40.894 (6)2.212 (12)2.863 (13)129 (3)
O2—H22···O1Di0.826 (5)1.906 (4)2.732 (7)179 (3)
Symmetry codes: (i) −x+1/2, y+1/2, −z+1/2; (ii) −x+1, −y+2, −z; (iii) x+1, y+1, z; (iv) x, y+1, z; (v) x+1/2, −y+3/2, z−1/2.
 

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