organic compounds\(\def\hfill{\hskip 5em}\def\hfil{\hskip 3em}\def\eqno#1{\hfil {#1}}\)

Journal logoCRYSTALLOGRAPHIC
COMMUNICATIONS
ISSN: 2056-9890
Volume 69| Part 3| March 2013| Pages o343-o344

Bis(2-carb­­oxy-N-{[1-(2-hy­dr­oxy­eth­yl)-3,3-di­methyl­indolin-2-yl­­idene]methyl­imino}­anilinium) sulfate monohydrate

aCarbohydrate Chemistry Group, Industrial Research Limited, PO Box 31-310, Lower Hutt, New Zealand, and bPhotonics Group, Industrial Research Limited, PO Box 31-310, Lower Hutt, New Zealand
*Correspondence e-mail: g.gainsford@irl.cri.nz

(Received 14 January 2013; accepted 30 January 2013; online 6 February 2013)

The asymmetric unit of the title compound, 2C20H22N3O3+·SO42−·H2O, contains four cations, two sulfate anions and two lattice water mol­ecules. One of the four cations shows a different conformation of the hy­droxy­ethyl group; the remaining three are all essentially superimposable. Two cations exhibit two-site orientational disorder [ratios = 0.524 (5):0.476 (5) and 0.616 (6):0.384 (6)] of the last two atoms of their hy­droxy­ethyl groups, and one water mol­ecule is disordered over two positions in a 0.634 (13):0.366 (13) ratio. Each imine H atom is intra­molecularly in contact with the adjacent carboxyl O atom, forming an S(6) motif, while all the carb­oxy­lic acid H atoms are hydrogen bonded to O atoms of the sulfate anions. Other notable hydrogen-bond inter­actions involve (methyl­ene, phenyl and imine chain) C—H⋯O (sulfate and carbox­yl) and O—H⋯O(water) contacts, making up a comprehensive three-dimensional network involving D22(n), with n = 4–6 and 15–16, and C22(17) classical hydrogen-bond motifs. The crystal investigated was twinned by pseudomerohedry with a twin component ratio of 0.4745 (12):0.5255 (12).

Related literature

For details of a related synthesis, see: Bhuiyan et al. (2011[Bhuiyan, M., Delower, H., Ashraf, M., Teshome, A., Gainsford, G. J., Kay, A. J., Asselberghs, I. & Clays, K. (2011). Dyes Pigm. 89, 177-187.]). For a closely related structure, see: Gainsford et al. (2013[Gainsford, G. J., Ashraf, M. & Kay, A. J. (2013). Unpublished work.]). For hydrogen-bonding motifs, see: Bernstein et al. (1995[Bernstein, J., Davis, R. E., Shimoni, L. & Chang, N.-L. (1995). Angew. Chem. Int. Ed. Engl. 34, 1555-1573.]).

[Scheme 1]

Experimental

Crystal data
  • 2C20H22N3O3+·SO42−·H2O

  • Mr = 816.88

  • Triclinic, [P \overline 1]

  • a = 12.2530 (9) Å

  • b = 14.6114 (3) Å

  • c = 23.2442 (4) Å

  • α = 71.681 (1)°

  • β = 87.688 (2)°

  • γ = 82.627 (7)°

  • V = 3917.9 (3) Å3

  • Z = 4

  • Cu Kα radiation

  • μ = 1.33 mm−1

  • T = 153 K

  • 0.68 × 0.40 × 0.24 mm

Data collection
  • Rigaku Spider diffractometer

  • Absorption correction: multi-scan (ABSCOR; Higashi, 1995[Higashi, T. (1995). ABSCOR. Rigaku Corporation, Tokyo, Japan.]) Tmin = 0.66, Tmax = 1.0

  • 24005 measured reflections

  • 10558 independent reflections

  • 9283 reflections with I > 2σ(I)

  • Rint = 0.044

  • θmax = 58.9°

Refinement
  • R[F2 > 2σ(F2)] = 0.053

  • wR(F2) = 0.152

  • S = 1.10

  • 10558 reflections

  • 1069 parameters

  • 2 restraints

  • H atoms treated by a mixture of independent and constrained refinement

  • Δρmax = 0.52 e Å−3

  • Δρmin = −0.53 e Å−3

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A D—H H⋯A DA D—H⋯A
O32A—H3A0⋯O101 0.84 1.94 2.644 (8) 140
O2—H2O⋯O14 0.84 1.66 2.457 (5) 158
N1—H1N⋯O1 0.70 (5) 2.08 (5) 2.652 (5) 139 (6)
O3—H3O⋯O13i 0.84 1.97 2.792 (5) 165
N101—H11N⋯O101 0.97 (5) 1.90 (5) 2.642 (6) 132 (4)
N201—H21N⋯O201 0.90 (5) 1.89 (6) 2.626 (6) 138 (5)
O203—H23O⋯O701ii 0.84 1.95 2.741 (6) 157
N301—H31N⋯O301 0.96 (5) 1.95 (5) 2.654 (5) 129 (4)
O102—H102⋯O21iii 0.84 1.68 2.509 (5) 169
O202—H202⋯O13iv 0.84 1.81 2.565 (5) 149
O302—H302⋯O22v 0.84 1.77 2.562 (6) 157
C8—H8⋯O11vi 0.95 2.55 3.402 (6) 150
C12B—H12C⋯O301 0.99 2.41 3.37 (2) 164
C15—H15⋯O12i 0.95 2.29 3.143 (6) 149
C19—H19B⋯O11vi 0.99 2.39 3.357 (7) 166
C20—H20B⋯O201vi 0.99 2.41 3.343 (6) 157
C220—H22B⋯O1vi 0.99 2.48 3.456 (6) 168
C39—H39B⋯O23 0.99 2.53 3.514 (7) 175
C108—H108⋯O24 0.95 2.26 3.073 (6) 143
C114—H114⋯O102vii 0.95 2.54 3.323 (7) 139
C115—H115⋯O23v 0.95 2.39 3.202 (7) 143
C205—H205⋯O21v 0.95 2.57 3.359 (7) 141
C208—H208⋯O12 0.95 2.26 3.119 (5) 150
C212—H212⋯O80A 0.95 2.60 3.486 (10) 156
C215—H215⋯O11vi 0.95 2.27 3.137 (7) 152
C306—H306⋯O203viii 0.95 2.36 3.154 (7) 140
C308—H308⋯O23 0.95 2.39 3.278 (6) 155
C315—H315⋯O24iii 0.95 2.26 3.150 (6) 156
Symmetry codes: (i) x, y+1, z; (ii) x-1, y, z; (iii) -x+1, -y+1, -z+1; (iv) -x, -y, -z; (v) -x+1, -y, -z+1; (vi) -x, -y+1, -z; (vii) x, y-1, z; (viii) x+1, y, z.

Data collection: CrystalClear (Rigaku, 2005[Rigaku (2005). CrystalClear. Rigaku Americas Corporation, The Woodlands, Texas, USA.]); cell refinement: FSProcess in PROCESS-AUTO (Rigaku, 1998[Rigaku (1998). PROCESS-AUTO. Rigaku Corporation, Tokyo, Japan.]); data reduction: FSProcess in PROCESS-AUTO; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); molecular graphics: WinGX (Farrugia, 2012[Farrugia, L. J. (2012). J. Appl. Cryst. 45, 849-854.]) and Mercury (Macrae et al., 2008[Macrae, C. F., Bruno, I. J., Chisholm, J. A., Edgington, P. R., McCabe, P., Pidcock, E., Rodriguez-Monge, L., Taylor, R., van de Streek, J. & Wood, P. A. (2008). J. Appl. Cryst. 41, 466-470.]); software used to prepare material for publication: SHELXL97 and PLATON (Spek, 2009[Spek, A. L. (2009). Acta Cryst. D65, 148-155.]).

Supporting information


Comment top

The title compound was prepared as part of our research into novel nonlinear optical (NLO) materials (Bhuiyan et al., 2011). It crystallizes with four independent C20H22N3O3+ cationic molecules, two sulfate anions and two lattice water molecules in the asymmetric unit (Fig. 2).

Each cation has atom labels related by the addition of 10 (e.g. N2, N102, N202, N302), hereafter assigned molecules 1, 2, 3 & 4. Three of the cations (1, 2 & 4) have identical conformations while molecule 3 has a different conformation for the bound hydroxyethyl group. In molecules 2 & 4 there is two-position disorder at the hydroxyethyl group: the partitioning is 0.476 (5):0.524 (5) and 0.616 (6):0.384 (6) for A:B sites in the respective cations. One of the water molecules (O80) is disordered over two sites (0.634 (13):0.366 (13)). The three similar conformation cations (1, 2 & 4) are essentially superimposable, except for the disordered hydroxyethyl atoms. There is bond length agreement (within experimental error) for the four cations, and also with those in a related uncharged structure: bis[(2-{[1-(2-hydroxy-ethyl)-3,3-dimethyl-1,3-dihydro-indol-2-ylidenemethyl]- azo}-benzoic acid)].3H2O (Gainsford et al., 2013).

Each imine (N—H) cationic proton is in contact intramolecularly with the adjacent carboxyl oxygen (with a S(6) motif; Bernstein et al., 1995), while all the carboxylic acid protons are hydrogen bonded to O atoms of the sulfate anions. Other notable hydrogen bonds (Table 1) involve (methylene, phenyl & imine chain) C—H···O (sulfate and carboxyl) and O—H···O(water) contacts, making up a comprehensive three-dimensional network involving D22(n), n = 4–6,15–16, and C22(17) classical bond motifs.

Related literature top

For details of a related synthesis, see: Bhuiyan et al. (2011). For a closely related structure, see: Gainsford et al. (2013). For hydrogen-bonding motifs, see: Bernstein et al. (1995).

Experimental top

To conc. sulfuric acid (4 ml) was added 2-aminobenzoic acid (2.5 mmol) and the reaction mixture cooled to 273–278 K. A solution of sodium nitrite (206 mg, 3 mmol) in 2 ml of water was then slowly added and the reaction stirred at 273–278 K for 30 min. To this was added a solution of 1-hydroxyethyl-3,3-trimethyl-2-methyleneindoline (2 mmol) in 10 ml of glacial acetic acid and the solution stirred for 2 h and allowed to gradually warm to room temperature (Fig. 1). At this point a solid was evident in the reaction mixture. This was collected by filtration, washed with water, dried and recrystallized from ethanol to give the title compound as orange crystals. The filtrate was then neutralized with aqueous sodium carbonate. This resulted in the formation of a second precipitate which after filtration, washing water and recrystallization from ethanol gave fine red needles subsequently identified as bis[(2-{[1-(2-hydroxy-ethyl)-3,3-dimethyl-1,3-dihydro-indol-2-ylidenemethyl]- azo}-benzoic acid)].3H2O (Gainsford et al., 2013).

Refinement top

Preliminary scans and initial processing indicated a monoclinic space group with cell parameters a = 14.6114 (3), b = 44.1324 (9), c = 12.2530 (8) Å and β = 97.373 (7)° [cell volume = 7835.9 (5) Å3]. Careful mapping established that there were 16 cations consistent with a final triclinic (halved volume) cell in space group P1. The model was converted to this cell using PLATON (Spek, 2009). Further analysis with PLATON then revealed that the crystal was twinned by pseudo-merohedry according to the matrix (-1 0 0 0 - 1 0 0 - 1 1); final twin components occupancies were 0.4745 (12):0.5255 (12). One water molecule (O701) was resolved while the other (O80A/O80B) was disordered over two main sites; the H atoms on these O atoms could not be located or calculated and so were not included in the refinement. Fixed occupancies for O80A and O80B (0.634 (13):0.366 (13)) were determined and individual isotropic U values were refined. Two site (conformational) disorder was also noted for the terminal C and O atoms of the ethyl alcohol groups on the second cation (C13 & O13) and the fourth cation (C32 & O32), with final occupancies of 0.476 (5):0.524 (5) and 0.616 (6):0.384 (6), respectively. Linked individual isotropic U values were refined for these atoms; H atoms on minor conformation atom C32B were fixed in calculated positions in the final cycles of refinement.

A total of 19 weak individual outlier reflections were omitted (using SHELXL OMIT) as outliers (Δ(F2)/e.s.d.(F2)> 6.2) as shown in the attached. RES file to give the final R1 of 0.053. Remaining poor agreement data were all measured as weak or unobserved at high resolution, with Fo2 << Fc2. There are 241 reflections missing within the final 0.90 Å shell with 26 low angle reflections affected by backstop interactions. An extinction parameter was refined.

All hydroxyl H atoms were constrained to an ideal geometry (0.84 Å) at the difference Fourier map positions (AFIX 147) with Uiso(H) = 1.2Ueq(O). The methyl H atoms were constrained to an ideal geometry (C—H = 0.98 Å) with Uiso(H) = 1.5Ueq(C), but were allowed to rotate freely about the adjacent C—C bond. Imine (N—H) protons were refined using their difference Fourier map assigned positions with Uiso(H) = 1.2Ueq(N). All other H atoms were placed in geometrically idealized positions and constrained o ride on their parent atoms with C—H distances of 1.00 (primary), 0.99 (methylene) or 0.95 (phenyl) Å with Uiso(H) = 1.2Ueq(C) except for H atoms on disordered atoms for which Uiso(H) = 1.5Ueq(C,O).

Computing details top

Data collection: CrystalClear (Rigaku, 2005); cell refinement: FSProcess in PROCESS-AUTO (Rigaku, 1998); data reduction: FSProcess in PROCESS-AUTO (Rigaku, 1998); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: WinGX (Farrugia, 2012) and Mercury (Macrae et al., 2008); software used to prepare material for publication: SHELXL97 (Sheldrick, 2008) and PLATON (Spek, 2009).

Figures top
[Figure 1] Fig. 1. Synthesis method for the title compound.
[Figure 2] Fig. 2. The atoms in the asymmetric unit with 35% probability ellipsoids. Some labels and all hydrogen atoms are omitted for clarity. Only the major conformers of the two site ethyl alcohol atoms are shown (see text).
Bis(2-carboxy-N-{[1-(2-hydroxyethyl)-3,3-dimethylindolin-2-ylidene]methylimino}anilinium) sulfate monohydrate top
Crystal data top
2C20H22N3O3+·SO42·H2OZ = 4
Mr = 816.88F(000) = 1724
Triclinic, P1Dx = 1.388 Mg m3
Hall symbol: -P 1Cu Kα radiation, λ = 1.54178 Å
a = 12.2530 (9) ÅCell parameters from 11451 reflections
b = 14.6114 (3) Åθ = 6.7–71.9°
c = 23.2442 (4) ŵ = 1.33 mm1
α = 71.681 (1)°T = 153 K
β = 87.688 (2)°Needle, orange
γ = 82.627 (7)°0.68 × 0.40 × 0.24 mm
V = 3917.9 (3) Å3
Data collection top
Rigaku Spider
diffractometer
10558 independent reflections
Radiation source: Rigaku MM007 rotating anode9283 reflections with I > 2σ(I)
Rigaku VariMax-HF Confocal Optical System monochromatorRint = 0.044
Detector resolution: 10 pixels mm-1θmax = 58.9°, θmin = 6.7°
ω–scansh = 1313
Absorption correction: multi-scan
(ABSCOR; Higashi, 1995)
k = 1612
Tmin = 0.66, Tmax = 1.0l = 2516
24005 measured reflections
Refinement top
Refinement on F2Secondary atom site location: difference Fourier map
Least-squares matrix: fullHydrogen site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.053H atoms treated by a mixture of independent and constrained refinement
wR(F2) = 0.152 w = 1/[σ2(Fo2) + (0.0892P)2 + 0.4584P]
where P = (Fo2 + 2Fc2)/3
S = 1.10(Δ/σ)max < 0.001
10558 reflectionsΔρmax = 0.52 e Å3
1069 parametersΔρmin = 0.53 e Å3
2 restraintsExtinction correction: SHELXL97 (Sheldrick, 2008), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
Primary atom site location: structure-invariant direct methodsExtinction coefficient: 0.00137 (15)
Crystal data top
2C20H22N3O3+·SO42·H2Oγ = 82.627 (7)°
Mr = 816.88V = 3917.9 (3) Å3
Triclinic, P1Z = 4
a = 12.2530 (9) ÅCu Kα radiation
b = 14.6114 (3) ŵ = 1.33 mm1
c = 23.2442 (4) ÅT = 153 K
α = 71.681 (1)°0.68 × 0.40 × 0.24 mm
β = 87.688 (2)°
Data collection top
Rigaku Spider
diffractometer
10558 independent reflections
Absorption correction: multi-scan
(ABSCOR; Higashi, 1995)
9283 reflections with I > 2σ(I)
Tmin = 0.66, Tmax = 1.0Rint = 0.044
24005 measured reflectionsθmax = 58.9°
Refinement top
R[F2 > 2σ(F2)] = 0.0532 restraints
wR(F2) = 0.152H atoms treated by a mixture of independent and constrained refinement
S = 1.10Δρmax = 0.52 e Å3
10558 reflectionsΔρmin = 0.53 e Å3
1069 parameters
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. Refined as a 2-component twin.

Reflections were merged by SHELXL according to the crystal class for the calculation of statistics and refinement.

_reflns_Friedel_fraction is defined as the number of unique Friedel pairs measured divided by the number that would be possible theoretically, ignoring centric projections and systematic absences. These statistics refer to single and composite reflections containing twin component 1 only.

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*/UeqOcc. (<1)
O10.2394 (2)0.4953 (2)0.00067 (15)0.0425 (8)
O20.2862 (3)0.3439 (2)0.00003 (18)0.0550 (10)
H2O0.22440.35380.01670.082*
O30.2575 (3)1.0269 (3)0.06476 (17)0.0570 (9)
H3O0.21371.07330.06010.086*
N10.3661 (3)0.5659 (3)0.06213 (19)0.0381 (10)
H1N0.321 (4)0.573 (4)0.043 (2)0.046*
N20.3953 (3)0.6389 (3)0.07792 (17)0.0357 (9)
N30.2953 (3)0.8848 (3)0.06109 (16)0.0349 (9)
C10.3040 (4)0.4204 (4)0.0130 (2)0.0380 (11)
C20.4078 (3)0.4070 (3)0.0485 (2)0.0349 (10)
C30.4809 (4)0.3241 (3)0.0577 (2)0.0405 (11)
H30.46410.27650.04050.049*
C40.5765 (4)0.3060 (4)0.0902 (2)0.0480 (13)
H40.62410.24700.09660.058*
C50.6008 (4)0.3790 (4)0.1137 (2)0.0483 (13)
H50.66720.36980.13560.058*
C60.5311 (4)0.4627 (4)0.1057 (2)0.0452 (12)
H60.54810.51010.12290.054*
C70.4349 (3)0.4786 (3)0.0721 (2)0.0355 (11)
C80.3284 (4)0.7187 (3)0.0620 (2)0.0367 (11)
H80.26210.72300.04100.044*
C90.3571 (4)0.8002 (3)0.0770 (2)0.0367 (11)
C100.4570 (4)0.8038 (3)0.1123 (2)0.0353 (10)
C110.4386 (4)0.9097 (3)0.1117 (2)0.0395 (11)
C120.5016 (4)0.9617 (3)0.1349 (2)0.0446 (12)
H120.56930.93260.15490.053*
C130.4631 (4)1.0566 (4)0.1279 (3)0.0521 (14)
H130.50341.09260.14540.063*
C140.3677 (4)1.1021 (4)0.0962 (2)0.0483 (13)
H140.34531.16890.09120.058*
C150.3037 (4)1.0507 (3)0.0714 (2)0.0421 (11)
H150.23741.08010.04990.050*
C160.3435 (4)0.9549 (3)0.0803 (2)0.0364 (11)
C170.5652 (4)0.7833 (4)0.0802 (3)0.0527 (14)
H17A0.56230.82540.03800.079*
H17B0.57550.71510.08130.079*
H17C0.62680.79620.10090.079*
C180.4534 (4)0.7345 (3)0.1778 (2)0.0433 (12)
H18A0.45950.66730.17720.065*
H18B0.38360.75010.19680.065*
H18C0.51470.74210.20100.065*
C190.1909 (4)0.9098 (4)0.0259 (2)0.0441 (12)
H19A0.14540.96360.03620.053*
H19B0.14930.85290.03800.053*
C200.2093 (4)0.9395 (4)0.0415 (2)0.0503 (13)
H20A0.25750.88680.05140.060*
H20B0.13780.94730.06190.060*
O1010.2709 (3)0.5022 (2)0.49747 (19)0.0560 (10)
O1020.2103 (3)0.6547 (2)0.49437 (19)0.0532 (9)
H1020.27280.66480.47940.080*
N1010.1521 (3)0.3627 (3)0.55596 (19)0.0436 (10)
H11N0.222 (4)0.380 (3)0.538 (2)0.052*
N1020.1256 (3)0.2723 (3)0.56968 (19)0.0423 (10)
N1030.2293 (3)0.0462 (2)0.54970 (17)0.0341 (9)
C1010.2017 (4)0.5614 (4)0.5104 (2)0.0486 (13)
C1020.1027 (4)0.5326 (3)0.5464 (2)0.0394 (11)
C1030.0256 (4)0.6039 (4)0.5589 (2)0.0467 (13)
H1030.03840.67000.54360.056*
C1040.0675 (4)0.5810 (4)0.5924 (2)0.0453 (12)
H1040.11960.63080.59890.054*
C1050.0849 (4)0.4839 (4)0.6169 (2)0.0516 (13)
H1050.14760.46760.64160.062*
C1060.0125 (4)0.4118 (4)0.6056 (2)0.0463 (13)
H1060.02600.34610.62250.056*
C1070.0807 (4)0.4335 (4)0.5697 (2)0.0427 (12)
C1080.1946 (4)0.2094 (3)0.5532 (2)0.0446 (12)
H1080.26140.22700.53310.054*
C1090.1666 (4)0.1144 (3)0.5662 (2)0.0353 (10)
C1100.0659 (3)0.0743 (3)0.6005 (2)0.0343 (10)
C1110.0845 (4)0.0269 (3)0.5995 (2)0.0371 (11)
C1120.0219 (4)0.1025 (4)0.6212 (2)0.0464 (13)
H1120.04580.09380.64140.056*
C1130.0593 (4)0.1928 (3)0.6132 (2)0.0475 (13)
H1130.01690.24540.62860.057*
C1140.1566 (4)0.2060 (4)0.5833 (2)0.0459 (12)
H1140.18040.26750.57840.055*
C1150.2206 (4)0.1303 (4)0.5603 (2)0.0463 (12)
H1150.28770.13890.53960.056*
C1160.1818 (3)0.0412 (3)0.5689 (2)0.0354 (10)
C1170.0632 (4)0.0801 (4)0.6656 (2)0.0486 (13)
H11A0.00070.05130.68700.073*
H11B0.05790.14820.66420.073*
H11C0.13070.04440.68690.073*
C1180.0400 (4)0.1281 (3)0.5662 (3)0.0485 (13)
H11D0.03310.13020.52370.073*
H11E0.05170.19450.56850.073*
H11F0.10270.09400.58460.073*
C1190.3262 (4)0.0599 (4)0.5101 (2)0.0444 (12)
H11G0.37830.00060.52180.053*
H11H0.36360.11240.51600.053*
O2010.0154 (3)0.0296 (3)0.12762 (16)0.0549 (9)
O2020.0235 (3)0.1928 (2)0.15901 (16)0.0527 (9)
H2020.00560.18600.12320.079*
O2030.0898 (3)0.3446 (3)0.15518 (17)0.0623 (10)
H23O0.11430.31620.13300.093*
N2010.1403 (3)0.0481 (3)0.18402 (19)0.0429 (10)
H21N0.100 (4)0.051 (4)0.152 (2)0.052*
N2020.1727 (3)0.1232 (3)0.19590 (19)0.0431 (10)
N2030.1385 (3)0.3820 (3)0.14242 (18)0.0403 (9)
C2010.0471 (4)0.1083 (4)0.1628 (2)0.0416 (12)
C2020.1215 (4)0.1230 (3)0.2154 (2)0.0370 (11)
C2030.1466 (4)0.2138 (4)0.2579 (2)0.0464 (12)
H2030.11450.26710.25350.056*
C2040.2158 (4)0.2302 (4)0.3060 (2)0.0511 (13)
H2040.23050.29320.33450.061*
C2050.2640 (4)0.1524 (4)0.3124 (3)0.0545 (14)
H2050.31330.16260.34490.065*
C2060.2403 (4)0.0616 (4)0.2718 (2)0.0503 (13)
H2060.27280.00890.27680.060*
C2070.1689 (4)0.0452 (3)0.2232 (2)0.0395 (11)
C2080.1423 (4)0.2094 (4)0.1587 (2)0.0456 (12)
H2080.10140.21790.12320.055*
C2090.1724 (4)0.2905 (4)0.1732 (2)0.0396 (11)
C2100.2454 (4)0.2845 (3)0.2258 (2)0.0380 (11)
C2110.2434 (4)0.3926 (4)0.2180 (2)0.0448 (12)
C2120.2887 (5)0.4385 (4)0.2527 (2)0.0525 (14)
H2120.33370.40260.28670.063*
C2130.2670 (5)0.5395 (4)0.2368 (3)0.0587 (15)
H2130.29910.57260.25980.070*
C2140.2002 (5)0.5921 (4)0.1886 (3)0.0579 (15)
H2140.18550.66060.17940.069*
C2150.1532 (4)0.5456 (4)0.1527 (3)0.0534 (13)
H2150.10820.58100.11860.064*
C2160.1763 (4)0.4451 (3)0.1697 (2)0.0387 (11)
C2170.3617 (4)0.2374 (4)0.2206 (3)0.0498 (13)
H21A0.40550.23670.25510.075*
H21B0.39510.27450.18280.075*
H21C0.35960.17070.22040.075*
C2180.1926 (5)0.2353 (4)0.2870 (2)0.0563 (15)
H21D0.11610.26460.28750.084*
H21E0.23370.24410.31980.084*
H21F0.19420.16580.29270.084*
C2190.0597 (4)0.4180 (4)0.0927 (2)0.0484 (13)
H21G0.06180.37080.07000.058*
H21H0.07860.48040.06450.058*
C2200.0559 (4)0.4327 (4)0.1189 (2)0.0582 (15)
H22A0.05600.47720.14340.070*
H22B0.10880.46350.08530.070*
O3010.5326 (3)0.0855 (2)0.37373 (16)0.0484 (9)
O3020.5300 (4)0.0437 (2)0.34318 (18)0.0624 (10)
H3020.48280.05800.37080.094*
N3010.6508 (3)0.2239 (3)0.31096 (19)0.0410 (9)
H31N0.596 (4)0.207 (3)0.342 (2)0.049*
N3020.6845 (3)0.3113 (3)0.29572 (18)0.0408 (9)
N3030.6494 (3)0.5197 (3)0.34567 (17)0.0380 (9)
C3010.5578 (4)0.0421 (3)0.3380 (2)0.0409 (11)
C3020.6339 (4)0.0764 (3)0.2857 (2)0.0378 (11)
C3030.6614 (4)0.0227 (3)0.2459 (2)0.0446 (12)
H3030.62640.03380.25110.054*
C3040.7359 (5)0.0471 (4)0.1999 (2)0.0533 (14)
H3040.75160.00950.17320.064*
C3050.7887 (4)0.1296 (4)0.1935 (2)0.0523 (13)
H3050.84350.14630.16320.063*
C3060.7623 (4)0.1868 (4)0.2305 (2)0.0467 (12)
H3060.79850.24250.22550.056*
C3070.6819 (4)0.1626 (3)0.2753 (2)0.0405 (11)
C3080.6496 (4)0.3640 (3)0.3307 (2)0.0382 (11)
H3080.60340.34060.36450.046*
C3090.6842 (4)0.4577 (3)0.3155 (2)0.0393 (11)
C3100.7633 (4)0.5041 (3)0.2650 (2)0.0370 (11)
C3110.7620 (4)0.6022 (3)0.2728 (2)0.0382 (11)
C3120.8157 (4)0.6804 (3)0.2401 (3)0.0520 (14)
H3120.86300.67670.20730.062*
C3130.7977 (5)0.7655 (4)0.2571 (3)0.0589 (15)
H3130.83370.82010.23560.071*
C3140.7280 (4)0.7707 (4)0.3049 (3)0.0518 (13)
H3140.71760.82880.31550.062*
C3150.6736 (4)0.6939 (3)0.3371 (2)0.0463 (13)
H3150.62480.69820.36920.056*
C3160.6931 (4)0.6100 (3)0.3205 (2)0.0408 (11)
C3170.8780 (4)0.4465 (4)0.2744 (2)0.0452 (12)
H31A0.90220.43480.31610.068*
H31B0.92970.48350.24600.068*
H31C0.87550.38420.26720.068*
C3180.7170 (4)0.5133 (4)0.2029 (2)0.0448 (12)
H31D0.72020.44860.19830.067*
H31E0.76090.55350.17090.067*
H31F0.64050.54360.19980.067*
S10.06408 (9)0.24937 (9)0.03304 (6)0.0409 (3)
O110.0552 (3)0.2821 (2)0.04153 (16)0.0511 (9)
O120.0915 (3)0.2003 (3)0.03033 (15)0.0565 (9)
O130.0984 (3)0.1842 (2)0.06986 (16)0.0544 (9)
O140.1239 (3)0.3376 (2)0.05672 (17)0.0568 (10)
S20.54556 (9)0.23700 (8)0.53390 (5)0.0383 (3)
O210.6139 (3)0.2948 (2)0.55787 (15)0.0459 (8)
O220.5804 (3)0.1314 (2)0.56443 (16)0.0493 (8)
O230.5641 (3)0.2580 (3)0.46818 (15)0.0506 (9)
O240.4308 (2)0.2617 (3)0.54699 (16)0.0550 (9)
O7010.8376 (3)0.2999 (3)0.05839 (18)0.0680 (11)
O13A0.2507 (6)0.0149 (5)0.4261 (4)0.0556 (13)*0.476 (5)
H13A0.18590.03650.41430.083*0.476 (5)
C12A0.297 (2)0.0848 (19)0.4455 (14)0.0506 (18)*0.476 (5)
H12A0.24440.14490.43510.076*0.476 (5)
H12B0.36450.10050.42140.076*0.476 (5)
C390.5651 (4)0.5077 (4)0.3938 (2)0.0515 (13)
H39A0.57960.54330.42200.077*
H39B0.56480.43820.41710.077*
C32A0.4486 (11)0.5519 (10)0.3593 (6)0.0733 (14)*0.616 (6)
H32A0.43880.62310.35130.110*0.616 (6)
H32B0.45230.53990.31960.110*0.616 (6)
O32A0.3578 (6)0.5154 (5)0.3896 (3)0.0733 (14)*0.616 (6)
H3AO0.34570.53530.41980.110*0.616 (6)
O80A0.3757 (7)0.3100 (7)0.4002 (4)0.0739 (17)*0.634 (13)
O80B0.3461 (12)0.3430 (11)0.4156 (6)0.0739 (17)*0.366 (13)
O13B0.2195 (5)0.1859 (5)0.4300 (3)0.0556 (13)*0.524 (5)
H13B0.25910.23110.42250.0739 (17)*0.524 (5)
C12B0.2868 (19)0.0965 (17)0.4437 (12)0.0506 (18)*0.524 (5)
H12C0.35160.10350.41650.076*0.524 (5)
H12D0.24530.04760.43600.076*0.524 (5)
O32B0.4336 (10)0.6167 (9)0.3458 (5)0.0733 (14)*0.384 (6)
H3BO0.40920.64860.36900.110*0.384 (6)
C32B0.4624 (18)0.5261 (15)0.3778 (9)0.0733 (14)*0.384 (6)
H32C0.41580.51060.41490.110*0.384 (6)
H32D0.44680.48350.35430.110*0.384 (6)
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
O10.0406 (17)0.0372 (19)0.054 (2)0.0068 (16)0.0109 (15)0.0182 (16)
O20.0453 (19)0.045 (2)0.088 (3)0.0001 (16)0.0196 (19)0.040 (2)
O30.065 (2)0.046 (2)0.058 (2)0.0045 (18)0.0084 (19)0.0147 (19)
N10.036 (2)0.041 (2)0.043 (3)0.0037 (19)0.0079 (18)0.020 (2)
N20.044 (2)0.027 (2)0.045 (2)0.0061 (18)0.0011 (18)0.0223 (18)
N30.0340 (19)0.038 (2)0.036 (2)0.0026 (17)0.0020 (16)0.0168 (18)
C10.035 (2)0.038 (3)0.048 (3)0.009 (2)0.001 (2)0.021 (2)
C20.036 (2)0.032 (2)0.038 (3)0.006 (2)0.001 (2)0.012 (2)
C30.043 (3)0.034 (3)0.050 (3)0.012 (2)0.002 (2)0.018 (2)
C40.044 (3)0.044 (3)0.056 (3)0.000 (2)0.006 (2)0.018 (3)
C50.037 (3)0.058 (3)0.058 (3)0.009 (2)0.008 (2)0.028 (3)
C60.048 (3)0.040 (3)0.055 (3)0.002 (2)0.014 (2)0.025 (3)
C70.037 (2)0.029 (3)0.042 (3)0.005 (2)0.000 (2)0.014 (2)
C80.040 (2)0.032 (3)0.044 (3)0.003 (2)0.005 (2)0.020 (2)
C90.040 (2)0.032 (3)0.037 (3)0.004 (2)0.003 (2)0.010 (2)
C100.042 (2)0.027 (2)0.041 (3)0.009 (2)0.001 (2)0.015 (2)
C110.044 (3)0.040 (3)0.042 (3)0.014 (2)0.002 (2)0.021 (2)
C120.046 (3)0.039 (3)0.060 (3)0.004 (2)0.000 (2)0.032 (3)
C130.051 (3)0.052 (3)0.068 (4)0.019 (3)0.011 (3)0.035 (3)
C140.054 (3)0.036 (3)0.060 (4)0.008 (2)0.015 (3)0.022 (3)
C150.045 (3)0.034 (3)0.045 (3)0.002 (2)0.002 (2)0.011 (2)
C160.043 (3)0.023 (2)0.048 (3)0.011 (2)0.007 (2)0.015 (2)
C170.037 (3)0.061 (3)0.070 (4)0.009 (2)0.003 (3)0.033 (3)
C180.053 (3)0.034 (3)0.046 (3)0.007 (2)0.004 (2)0.016 (2)
C190.035 (2)0.046 (3)0.052 (3)0.003 (2)0.007 (2)0.015 (2)
C200.050 (3)0.045 (3)0.052 (3)0.006 (2)0.014 (2)0.012 (3)
O1010.0378 (18)0.039 (2)0.084 (3)0.0081 (16)0.0055 (19)0.0087 (19)
O1020.049 (2)0.0308 (19)0.083 (3)0.0166 (15)0.0041 (19)0.0187 (18)
N1010.040 (2)0.034 (2)0.054 (3)0.0032 (19)0.001 (2)0.012 (2)
N1020.039 (2)0.032 (2)0.052 (3)0.0088 (18)0.0055 (19)0.0050 (19)
N1030.0327 (19)0.024 (2)0.050 (2)0.0058 (16)0.0011 (17)0.0157 (18)
C1010.031 (3)0.058 (4)0.051 (3)0.007 (3)0.010 (2)0.008 (3)
C1020.037 (2)0.041 (3)0.041 (3)0.013 (2)0.008 (2)0.011 (2)
C1030.042 (3)0.051 (3)0.048 (3)0.005 (2)0.015 (2)0.015 (3)
C1040.042 (3)0.041 (3)0.058 (3)0.011 (2)0.004 (2)0.019 (3)
C1050.044 (3)0.055 (4)0.056 (3)0.010 (3)0.002 (2)0.016 (3)
C1060.050 (3)0.039 (3)0.058 (3)0.021 (2)0.001 (2)0.019 (3)
C1070.038 (3)0.045 (3)0.042 (3)0.009 (2)0.008 (2)0.007 (2)
C1080.035 (2)0.044 (3)0.054 (3)0.005 (2)0.001 (2)0.013 (2)
C1090.041 (2)0.026 (2)0.039 (3)0.011 (2)0.007 (2)0.007 (2)
C1100.037 (2)0.019 (2)0.050 (3)0.0015 (19)0.002 (2)0.015 (2)
C1110.040 (2)0.030 (3)0.038 (3)0.002 (2)0.004 (2)0.006 (2)
C1120.042 (3)0.047 (3)0.052 (3)0.017 (2)0.008 (2)0.014 (3)
C1130.055 (3)0.031 (3)0.057 (3)0.006 (2)0.004 (3)0.014 (2)
C1140.049 (3)0.037 (3)0.053 (3)0.010 (2)0.009 (3)0.014 (2)
C1150.038 (3)0.061 (3)0.041 (3)0.010 (2)0.007 (2)0.023 (3)
C1160.035 (2)0.029 (3)0.042 (3)0.0041 (19)0.003 (2)0.014 (2)
C1170.045 (3)0.055 (3)0.051 (3)0.016 (2)0.006 (2)0.022 (3)
C1180.039 (3)0.040 (3)0.065 (4)0.003 (2)0.007 (2)0.014 (3)
C1190.037 (3)0.042 (3)0.055 (3)0.005 (2)0.002 (2)0.017 (3)
O2010.064 (2)0.048 (2)0.050 (2)0.0064 (18)0.0194 (18)0.0101 (19)
O2020.068 (2)0.051 (2)0.046 (2)0.0135 (18)0.0121 (18)0.0212 (18)
O2030.060 (2)0.066 (3)0.059 (2)0.023 (2)0.0091 (19)0.012 (2)
N2010.049 (2)0.039 (2)0.047 (3)0.0161 (19)0.006 (2)0.017 (2)
N2020.043 (2)0.044 (3)0.048 (3)0.0132 (19)0.0006 (19)0.019 (2)
N2030.041 (2)0.035 (2)0.045 (2)0.0029 (18)0.0012 (19)0.0134 (19)
C2010.046 (3)0.050 (3)0.039 (3)0.016 (2)0.004 (2)0.025 (3)
C2020.045 (3)0.034 (3)0.038 (3)0.014 (2)0.011 (2)0.018 (2)
C2030.050 (3)0.048 (3)0.046 (3)0.010 (2)0.010 (2)0.021 (3)
C2040.058 (3)0.052 (3)0.046 (3)0.013 (3)0.002 (3)0.017 (3)
C2050.056 (3)0.060 (4)0.048 (3)0.008 (3)0.008 (3)0.015 (3)
C2060.053 (3)0.050 (3)0.057 (3)0.015 (3)0.005 (3)0.026 (3)
C2070.042 (3)0.039 (3)0.040 (3)0.010 (2)0.005 (2)0.016 (2)
C2080.040 (3)0.056 (3)0.043 (3)0.006 (2)0.001 (2)0.019 (3)
C2090.035 (2)0.047 (3)0.043 (3)0.007 (2)0.006 (2)0.023 (2)
C2100.054 (3)0.022 (2)0.042 (3)0.008 (2)0.003 (2)0.015 (2)
C2110.048 (3)0.045 (3)0.039 (3)0.010 (2)0.008 (2)0.008 (2)
C2120.070 (3)0.039 (3)0.052 (3)0.002 (3)0.009 (3)0.019 (3)
C2130.075 (4)0.048 (3)0.063 (4)0.014 (3)0.012 (3)0.030 (3)
C2140.075 (4)0.033 (3)0.058 (4)0.002 (3)0.013 (3)0.009 (3)
C2150.050 (3)0.052 (3)0.052 (3)0.005 (3)0.006 (3)0.008 (3)
C2160.049 (3)0.020 (2)0.048 (3)0.000 (2)0.008 (2)0.014 (2)
C2170.047 (3)0.047 (3)0.060 (3)0.003 (2)0.014 (3)0.023 (3)
C2180.086 (4)0.037 (3)0.046 (3)0.014 (3)0.008 (3)0.011 (3)
C2190.050 (3)0.046 (3)0.045 (3)0.008 (2)0.003 (2)0.008 (2)
C2200.046 (3)0.068 (4)0.047 (3)0.009 (3)0.006 (3)0.003 (3)
O3010.058 (2)0.0355 (19)0.058 (2)0.0206 (16)0.0082 (17)0.0188 (18)
O3020.100 (3)0.037 (2)0.059 (3)0.034 (2)0.013 (2)0.0200 (18)
N3010.045 (2)0.040 (2)0.045 (2)0.0125 (18)0.0037 (19)0.020 (2)
N3020.045 (2)0.037 (2)0.042 (2)0.0101 (18)0.0037 (18)0.012 (2)
N3030.040 (2)0.044 (2)0.036 (2)0.0138 (18)0.0023 (17)0.0167 (19)
C3010.053 (3)0.026 (2)0.044 (3)0.014 (2)0.010 (2)0.007 (2)
C3020.044 (3)0.028 (3)0.039 (3)0.005 (2)0.009 (2)0.008 (2)
C3030.065 (3)0.028 (3)0.047 (3)0.010 (2)0.012 (3)0.018 (2)
C3040.075 (4)0.048 (3)0.037 (3)0.012 (3)0.004 (3)0.011 (2)
C3050.064 (3)0.052 (3)0.043 (3)0.015 (3)0.005 (3)0.016 (3)
C3060.051 (3)0.046 (3)0.043 (3)0.011 (2)0.005 (2)0.012 (3)
C3070.048 (3)0.041 (3)0.034 (3)0.011 (2)0.006 (2)0.011 (2)
C3080.041 (2)0.039 (3)0.035 (3)0.011 (2)0.004 (2)0.012 (2)
C3090.043 (3)0.042 (3)0.039 (3)0.008 (2)0.006 (2)0.019 (2)
C3100.037 (2)0.043 (3)0.037 (3)0.011 (2)0.004 (2)0.018 (2)
C3110.046 (3)0.026 (2)0.048 (3)0.005 (2)0.001 (2)0.019 (2)
C3120.066 (3)0.034 (3)0.055 (3)0.012 (2)0.010 (3)0.011 (3)
C3130.078 (4)0.035 (3)0.067 (4)0.016 (3)0.003 (3)0.018 (3)
C3140.070 (3)0.037 (3)0.057 (3)0.007 (3)0.009 (3)0.027 (3)
C3150.056 (3)0.041 (3)0.050 (3)0.001 (2)0.005 (2)0.028 (3)
C3160.045 (3)0.041 (3)0.040 (3)0.009 (2)0.001 (2)0.017 (2)
C3170.041 (3)0.056 (3)0.040 (3)0.010 (2)0.001 (2)0.016 (2)
C3180.049 (3)0.051 (3)0.038 (3)0.016 (2)0.006 (2)0.014 (2)
S10.0396 (6)0.0418 (7)0.0452 (8)0.0059 (5)0.0093 (5)0.0176 (6)
O110.0412 (18)0.048 (2)0.065 (2)0.0019 (16)0.0161 (17)0.0206 (19)
O120.058 (2)0.066 (2)0.041 (2)0.0004 (18)0.0133 (17)0.0116 (19)
O130.063 (2)0.051 (2)0.063 (2)0.0035 (17)0.0159 (18)0.0389 (19)
O140.059 (2)0.037 (2)0.078 (3)0.0220 (17)0.0202 (19)0.0146 (19)
S20.0358 (6)0.0413 (7)0.0395 (7)0.0087 (5)0.0016 (5)0.0138 (6)
O210.0521 (19)0.0420 (19)0.055 (2)0.0208 (15)0.0017 (16)0.0253 (17)
O220.064 (2)0.0286 (18)0.052 (2)0.0103 (16)0.0005 (17)0.0065 (16)
O230.0484 (19)0.062 (2)0.0366 (19)0.0041 (17)0.0005 (16)0.0132 (17)
O240.0329 (17)0.076 (3)0.060 (2)0.0076 (17)0.0079 (16)0.027 (2)
O7010.060 (2)0.076 (3)0.071 (3)0.010 (2)0.002 (2)0.027 (2)
C390.049 (3)0.062 (4)0.045 (3)0.012 (3)0.015 (2)0.020 (3)
Geometric parameters (Å, º) top
O1—C11.227 (5)C201—C2021.500 (7)
O2—C11.292 (5)C202—C2031.389 (7)
O2—H2O0.8400C202—C2071.403 (6)
O3—C201.417 (6)C203—C2041.372 (7)
O3—H3O0.8400C203—H2030.9500
N1—N21.325 (5)C204—C2051.395 (7)
N1—C71.395 (6)C204—H2040.9500
N1—H1N0.70 (5)C205—C2061.368 (7)
N2—C81.295 (5)C205—H2050.9500
N3—C91.317 (5)C206—C2071.399 (7)
N3—C161.435 (5)C206—H2060.9500
N3—C191.488 (5)C208—C2091.422 (6)
C1—C21.501 (6)C208—H2080.9500
C2—C31.374 (6)C209—C2101.519 (6)
C2—C71.404 (6)C210—C2171.518 (7)
C3—C41.372 (6)C210—C2111.530 (6)
C3—H30.9500C210—C2181.537 (7)
C4—C51.409 (7)C211—C2121.372 (7)
C4—H40.9500C211—C2161.376 (7)
C5—C61.364 (7)C212—C2131.396 (7)
C5—H50.9500C212—H2120.9500
C6—C71.393 (6)C213—C2141.373 (8)
C6—H60.9500C213—H2130.9500
C8—C91.427 (6)C214—C2151.410 (8)
C8—H80.9500C214—H2140.9500
C9—C101.516 (6)C215—C2161.389 (7)
C10—C111.530 (6)C215—H2150.9500
C10—C171.537 (7)C217—H21A0.9800
C10—C181.545 (6)C217—H21B0.9800
C11—C161.376 (6)C217—H21C0.9800
C11—C121.381 (6)C218—H21D0.9800
C12—C131.366 (7)C218—H21E0.9800
C12—H120.9500C218—H21F0.9800
C13—C141.383 (7)C219—C2201.535 (7)
C13—H130.9500C219—H21G0.9900
C14—C151.405 (7)C219—H21H0.9900
C14—H140.9500C220—H22A0.9900
C15—C161.375 (6)C220—H22B0.9900
C15—H150.9500O301—C3011.204 (5)
C17—H17A0.9800O302—C3011.309 (5)
C17—H17B0.9800O302—H3020.8400
C17—H17C0.9800N301—N3021.330 (5)
C18—H18A0.9800N301—C3071.410 (6)
C18—H18B0.9800N301—H31N0.96 (5)
C18—H18C0.9800N302—C3081.310 (6)
C19—C201.504 (7)N303—C3091.332 (6)
C19—H19A0.9900N303—C3161.428 (6)
C19—H19B0.9900N303—C391.476 (6)
C20—H20A0.9900C301—C3021.497 (7)
C20—H20B0.9900C302—C3031.396 (6)
O101—C1011.230 (6)C302—C3071.405 (6)
O102—C1011.312 (6)C303—C3041.368 (7)
O102—H1020.8400C303—H3030.9500
N101—N1021.336 (5)C304—C3051.405 (7)
N101—C1071.374 (6)C304—H3040.9500
N101—H11N0.97 (5)C305—C3061.378 (7)
N102—C1081.305 (6)C305—H3050.9500
N103—C1091.322 (5)C306—C3071.399 (7)
N103—C1161.407 (5)C306—H3060.9500
N103—C1191.467 (6)C308—C3091.418 (6)
C101—C1021.475 (7)C308—H3080.9500
C102—C1031.406 (7)C309—C3101.534 (6)
C102—C1071.435 (6)C310—C3111.497 (6)
C103—C1041.373 (7)C310—C3171.528 (6)
C103—H1030.9500C310—C3181.533 (6)
C104—C1051.393 (7)C311—C3121.387 (7)
C104—H1040.9500C311—C3161.392 (7)
C105—C1061.371 (7)C312—C3131.408 (7)
C105—H1050.9500C312—H3120.9500
C106—C1071.398 (7)C313—C3141.388 (8)
C106—H1060.9500C313—H3130.9500
C108—C1091.410 (6)C314—C3151.374 (7)
C108—H1080.9500C314—H3140.9500
C109—C1101.521 (6)C315—C3161.387 (6)
C110—C1111.474 (6)C315—H3150.9500
C110—C1181.539 (6)C317—H31A0.9800
C110—C1171.539 (6)C317—H31B0.9800
C111—C1121.379 (6)C317—H31C0.9800
C111—C1161.391 (6)C318—H31D0.9800
C112—C1131.405 (7)C318—H31E0.9800
C112—H1120.9500C318—H31F0.9800
C113—C1141.379 (7)S1—O121.453 (4)
C113—H1130.9500S1—O111.479 (3)
C114—C1151.392 (7)S1—O131.482 (3)
C114—H1140.9500S1—O141.505 (3)
C115—C1161.399 (6)S2—O241.450 (3)
C115—H1150.9500S2—O231.475 (3)
C117—H11A0.9800S2—O211.496 (3)
C117—H11B0.9800S2—O221.494 (3)
C117—H11C0.9800O13A—C12A1.42 (3)
C118—H11D0.9800O13A—H13A0.8400
C118—H11E0.9800C12A—H12A0.9900
C118—H11F0.9800C12A—H12B0.9900
C119—C12A1.48 (3)C39—C32A1.621 (13)
C119—C12B1.54 (3)C39—H39A0.9900
C119—H11G0.9900C39—H39B0.9900
C119—H11H0.9900C32A—O32A1.367 (15)
O201—C2011.209 (6)C32A—H32A0.9900
O202—C2011.333 (6)C32A—H32B0.9900
O202—H2020.8400O32A—H3AO0.8400
O203—C2201.403 (6)O13B—C12B1.40 (2)
O203—H23O0.8400O13B—H13B0.8400
N201—N2021.324 (5)C12B—H12C0.9900
N201—C2071.390 (6)C12B—H12D0.9900
N201—H21N0.90 (5)O32B—C32B1.31 (2)
N202—C2081.301 (6)O32B—H3BO0.8400
N203—C2091.324 (6)C32B—H32C1.00 (2)
N203—C2161.403 (6)C32B—H32D0.99 (2)
N203—C2191.457 (6)
C1—O2—H2O109.5C203—C204—C205118.7 (5)
C20—O3—H3O109.5C203—C204—H204120.6
N2—N1—C7121.7 (4)C205—C204—H204120.6
N2—N1—H1N121 (5)C206—C205—C204120.1 (5)
C7—N1—H1N116 (4)C206—C205—H205119.9
C8—N2—N1115.9 (4)C204—C205—H205119.9
C9—N3—C16111.1 (4)C205—C206—C207120.9 (5)
C9—N3—C19126.6 (4)C205—C206—H206119.5
C16—N3—C19122.3 (4)C207—C206—H206119.5
O1—C1—O2123.3 (4)N201—C207—C206120.8 (4)
O1—C1—C2122.9 (4)N201—C207—C202119.4 (4)
O2—C1—C2113.7 (4)C206—C207—C202119.7 (5)
C3—C2—C7117.8 (4)N202—C208—C209117.7 (4)
C3—C2—C1120.4 (4)N202—C208—H208121.2
C7—C2—C1121.7 (4)C209—C208—H208121.2
C2—C3—C4123.8 (4)N203—C209—C208123.9 (4)
C2—C3—H3118.1N203—C209—C210110.9 (4)
C4—C3—H3118.1C208—C209—C210125.2 (4)
C3—C4—C5116.9 (5)C209—C210—C217112.9 (4)
C3—C4—H4121.6C209—C210—C211100.0 (4)
C5—C4—H4121.6C217—C210—C211111.2 (4)
C6—C5—C4121.5 (4)C209—C210—C218111.4 (4)
C6—C5—H5119.2C217—C210—C218111.9 (4)
C4—C5—H5119.2C211—C210—C218108.7 (4)
C5—C6—C7119.9 (4)C212—C211—C216120.5 (5)
C5—C6—H6120.1C212—C211—C210130.7 (5)
C7—C6—H6120.1C216—C211—C210108.6 (4)
N1—C7—C6119.6 (4)C211—C212—C213118.2 (5)
N1—C7—C2120.4 (4)C211—C212—H212120.9
C6—C7—C2120.0 (4)C213—C212—H212120.9
N2—C8—C9118.1 (4)C214—C213—C212121.4 (5)
N2—C8—H8120.9C214—C213—H213119.3
C9—C8—H8120.9C212—C213—H213119.3
N3—C9—C8122.0 (4)C213—C214—C215120.8 (5)
N3—C9—C10110.7 (4)C213—C214—H214119.6
C8—C9—C10127.3 (4)C215—C214—H214119.6
C9—C10—C11100.6 (4)C216—C215—C214116.4 (5)
C9—C10—C17112.1 (4)C216—C215—H215121.8
C11—C10—C17110.9 (4)C214—C215—H215121.8
C9—C10—C18110.4 (4)C211—C216—C215122.7 (5)
C11—C10—C18110.4 (4)C211—C216—N203109.7 (4)
C17—C10—C18111.9 (4)C215—C216—N203127.6 (5)
C16—C11—C12120.0 (4)C210—C217—H21A109.5
C16—C11—C10109.2 (4)C210—C217—H21B109.5
C12—C11—C10130.8 (4)H21A—C217—H21B109.5
C13—C12—C11117.6 (5)C210—C217—H21C109.5
C13—C12—H12121.2H21A—C217—H21C109.5
C11—C12—H12121.2H21B—C217—H21C109.5
C12—C13—C14122.4 (5)C210—C218—H21D109.5
C12—C13—H13118.8C210—C218—H21E109.5
C14—C13—H13118.8H21D—C218—H21E109.5
C13—C14—C15120.7 (5)C210—C218—H21F109.5
C13—C14—H14119.7H21D—C218—H21F109.5
C15—C14—H14119.7H21E—C218—H21F109.5
C16—C15—C14115.5 (5)N203—C219—C220108.7 (4)
C16—C15—H15122.3N203—C219—H21G109.9
C14—C15—H15122.3C220—C219—H21G109.9
C15—C16—C11123.8 (4)N203—C219—H21H109.9
C15—C16—N3127.8 (4)C220—C219—H21H109.9
C11—C16—N3108.4 (4)H21G—C219—H21H108.3
C10—C17—H17A109.5O203—C220—C219111.8 (5)
C10—C17—H17B109.5O203—C220—H22A109.3
H17A—C17—H17B109.5C219—C220—H22A109.3
C10—C17—H17C109.5O203—C220—H22B109.3
H17A—C17—H17C109.5C219—C220—H22B109.3
H17B—C17—H17C109.5H22A—C220—H22B107.9
C10—C18—H18A109.5C301—O302—H302109.5
C10—C18—H18B109.5N302—N301—C307119.8 (4)
H18A—C18—H18B109.5N302—N301—H31N120 (3)
C10—C18—H18C109.5C307—N301—H31N120 (3)
H18A—C18—H18C109.5C308—N302—N301115.5 (4)
H18B—C18—H18C109.5C309—N303—C316111.5 (4)
N3—C19—C20112.9 (4)C309—N303—C39127.2 (4)
N3—C19—H19A109.0C316—N303—C39120.9 (4)
C20—C19—H19A109.0O301—C301—O302124.1 (4)
N3—C19—H19B109.0O301—C301—C302123.3 (4)
C20—C19—H19B109.0O302—C301—C302112.4 (4)
H19A—C19—H19B107.8C303—C302—C307117.4 (4)
O3—C20—C19113.8 (4)C303—C302—C301120.9 (4)
O3—C20—H20A108.8C307—C302—C301121.7 (4)
C19—C20—H20A108.8C304—C303—C302123.4 (4)
O3—C20—H20B108.8C304—C303—H303118.3
C19—C20—H20B108.8C302—C303—H303118.3
H20A—C20—H20B107.7C303—C304—C305117.8 (5)
C101—O102—H102109.5C303—C304—H304121.1
N102—N101—C107120.0 (4)C305—C304—H304121.1
N102—N101—H11N122 (3)C306—C305—C304121.1 (5)
C107—N101—H11N118 (3)C306—C305—H305119.4
C108—N102—N101117.1 (4)C304—C305—H305119.4
C109—N103—C116110.1 (3)C305—C306—C307119.8 (5)
C109—N103—C119126.4 (4)C305—C306—H306120.1
C116—N103—C119123.0 (4)C307—C306—H306120.1
O101—C101—O102123.2 (5)C306—C307—C302120.2 (4)
O101—C101—C102122.4 (5)C306—C307—N301119.7 (4)
O102—C101—C102114.5 (5)C302—C307—N301120.1 (4)
C103—C102—C107117.7 (4)N302—C308—C309116.7 (4)
C103—C102—C101119.7 (4)N302—C308—H308121.6
C107—C102—C101122.6 (5)C309—C308—H308121.6
C104—C103—C102122.1 (5)N303—C309—C308122.1 (4)
C104—C103—H103119.0N303—C309—C310109.5 (4)
C102—C103—H103119.0C308—C309—C310128.3 (4)
C103—C104—C105119.4 (5)C311—C310—C317112.3 (4)
C103—C104—H104120.3C311—C310—C309101.1 (4)
C105—C104—H104120.3C317—C310—C309111.3 (4)
C106—C105—C104120.7 (5)C311—C310—C318110.6 (4)
C106—C105—H105119.6C317—C310—C318110.9 (4)
C104—C105—H105119.6C309—C310—C318110.3 (4)
C105—C106—C107121.1 (5)C312—C311—C316119.7 (4)
C105—C106—H106119.5C312—C311—C310130.1 (4)
C107—C106—H106119.5C316—C311—C310110.2 (4)
N101—C107—C106122.0 (4)C311—C312—C313117.8 (5)
N101—C107—C102119.0 (4)C311—C312—H312121.1
C106—C107—C102119.0 (5)C313—C312—H312121.1
N102—C108—C109117.7 (4)C314—C313—C312120.8 (5)
N102—C108—H108121.1C314—C313—H313119.6
C109—C108—H108121.1C312—C313—H313119.6
N103—C109—C108122.4 (4)C315—C314—C313121.8 (5)
N103—C109—C110110.5 (3)C315—C314—H314119.1
C108—C109—C110127.1 (4)C313—C314—H314119.1
C111—C110—C109100.9 (3)C314—C315—C316116.9 (5)
C111—C110—C118110.9 (4)C314—C315—H315121.5
C109—C110—C118110.5 (4)C316—C315—H315121.5
C111—C110—C117112.0 (4)C315—C316—C311123.0 (4)
C109—C110—C117111.4 (4)C315—C316—N303129.4 (4)
C118—C110—C117110.8 (4)C311—C316—N303107.7 (4)
C112—C111—C116119.1 (4)C310—C317—H31A109.5
C112—C111—C110131.3 (4)C310—C317—H31B109.5
C116—C111—C110109.7 (4)H31A—C317—H31B109.5
C111—C112—C113119.3 (5)C310—C317—H31C109.5
C111—C112—H112120.4H31A—C317—H31C109.5
C113—C112—H112120.4H31B—C317—H31C109.5
C114—C113—C112120.9 (5)C310—C318—H31D109.5
C114—C113—H113119.6C310—C318—H31E109.5
C112—C113—H113119.6H31D—C318—H31E109.5
C113—C114—C115120.9 (5)C310—C318—H31F109.5
C113—C114—H114119.5H31D—C318—H31F109.5
C115—C114—H114119.5H31E—C318—H31F109.5
C114—C115—C116117.2 (4)O12—S1—O11111.7 (2)
C114—C115—H115121.4O12—S1—O13110.4 (2)
C116—C115—H115121.4O11—S1—O13109.16 (19)
C111—C116—C115122.7 (4)O12—S1—O14109.9 (2)
C111—C116—N103108.7 (4)O11—S1—O14107.74 (19)
C115—C116—N103128.6 (4)O13—S1—O14107.9 (2)
C110—C117—H11A109.5O24—S2—O23111.2 (2)
C110—C117—H11B109.5O24—S2—O21108.6 (2)
H11A—C117—H11B109.5O23—S2—O21109.7 (2)
C110—C117—H11C109.5O24—S2—O22110.1 (2)
H11A—C117—H11C109.5O23—S2—O22108.5 (2)
H11B—C117—H11C109.5O21—S2—O22108.7 (2)
C110—C118—H11D109.5C12A—O13A—H13A109.5
C110—C118—H11E109.5O13A—C12A—C119118.4 (19)
H11D—C118—H11E109.5O13A—C12A—H12A107.7
C110—C118—H11F109.5C119—C12A—H12A107.7
H11D—C118—H11F109.5O13A—C12A—H12B107.7
H11E—C118—H11F109.5C119—C12A—H12B107.7
N103—C119—C12A112.2 (11)H12A—C12A—H12B107.1
N103—C119—C12B108.4 (10)N303—C39—C32A105.8 (6)
N103—C119—H11G109.2N303—C39—H39A110.6
C12A—C119—H11G109.2C32A—C39—H39A110.6
N103—C119—H11H109.2N303—C39—H39B110.6
C12A—C119—H11H109.2C32A—C39—H39B110.6
H11G—C119—H11H107.9H39A—C39—H39B108.7
C201—O202—H202109.5O32A—C32A—C39115.6 (8)
C220—O203—H23O109.5O32A—C32A—H32A108.4
N202—N201—C207119.7 (4)C39—C32A—H32A108.4
N202—N201—H21N125 (3)O32A—C32A—H32B108.4
C207—N201—H21N115 (3)C39—C32A—H32B108.4
C208—N202—N201117.7 (4)H32A—C32A—H32B107.4
C209—N203—C216110.6 (4)C32A—O32A—H3AO109.5
C209—N203—C219127.8 (4)C12B—O13B—H13B109.5
C216—N203—C219121.0 (4)O13B—C12B—C119112.3 (17)
O201—C201—O202124.9 (4)O13B—C12B—H12C109.2
O201—C201—C202123.7 (4)C119—C12B—H12C109.2
O202—C201—C202111.4 (4)O13B—C12B—H12D109.2
C203—C202—C207117.6 (4)C119—C12B—H12D109.2
C203—C202—C201121.4 (4)H12C—C12B—H12D107.9
C207—C202—C201121.0 (4)C32B—O32B—H3BO109.5
C204—C203—C202122.9 (5)O32B—C32B—H32C108.3 (19)
C204—C203—H203118.5O32B—C32B—H32D109.2 (17)
C202—C203—H203118.5H32C—C32B—H32D107 (2)
C7—N1—N2—C8174.7 (4)O201—C201—C202—C203173.4 (5)
O1—C1—C2—C3175.7 (5)O202—C201—C202—C2038.3 (6)
O2—C1—C2—C38.1 (6)O201—C201—C202—C2077.0 (7)
O1—C1—C2—C72.9 (7)O202—C201—C202—C207171.2 (4)
O2—C1—C2—C7173.3 (4)C207—C202—C203—C2040.7 (7)
C7—C2—C3—C42.2 (7)C201—C202—C203—C204178.9 (5)
C1—C2—C3—C4179.1 (4)C202—C203—C204—C2050.6 (8)
C2—C3—C4—C51.8 (8)C203—C204—C205—C2061.4 (8)
C3—C4—C5—C61.5 (8)C204—C205—C206—C2070.8 (8)
C4—C5—C6—C71.9 (8)N202—N201—C207—C2066.1 (7)
N2—N1—C7—C67.5 (7)N202—N201—C207—C202170.8 (4)
N2—N1—C7—C2172.3 (4)C205—C206—C207—N201176.4 (5)
C5—C6—C7—N1177.5 (5)C205—C206—C207—C2020.6 (8)
C5—C6—C7—C22.3 (7)C203—C202—C207—N201175.7 (4)
C3—C2—C7—N1177.4 (4)C201—C202—C207—N2014.7 (7)
C1—C2—C7—N11.2 (7)C203—C202—C207—C2061.3 (7)
C3—C2—C7—C62.4 (7)C201—C202—C207—C206178.3 (4)
C1—C2—C7—C6178.9 (4)N201—N202—C208—C209176.8 (4)
N1—N2—C8—C9178.9 (4)C216—N203—C209—C208176.3 (4)
C16—N3—C9—C8178.6 (4)C219—N203—C209—C2085.3 (7)
C19—N3—C9—C80.8 (7)C216—N203—C209—C2102.8 (5)
C16—N3—C9—C101.9 (5)C219—N203—C209—C210173.8 (4)
C19—N3—C9—C10179.7 (4)N202—C208—C209—N203173.6 (4)
N2—C8—C9—N3178.1 (4)N202—C208—C209—C2105.4 (7)
N2—C8—C9—C102.4 (7)N203—C209—C210—C217117.6 (4)
N3—C9—C10—C110.9 (5)C208—C209—C210—C21763.3 (6)
C8—C9—C10—C11179.6 (4)N203—C209—C210—C2110.7 (5)
N3—C9—C10—C17118.7 (4)C208—C209—C210—C211178.4 (4)
C8—C9—C10—C1761.8 (6)N203—C209—C210—C218115.5 (4)
N3—C9—C10—C18115.8 (4)C208—C209—C210—C21863.6 (6)
C8—C9—C10—C1863.7 (6)C209—C210—C211—C212176.3 (5)
C9—C10—C11—C160.5 (5)C217—C210—C211—C21264.2 (7)
C17—C10—C11—C16118.3 (4)C218—C210—C211—C21259.5 (7)
C18—C10—C11—C16117.2 (4)C209—C210—C211—C2161.7 (5)
C9—C10—C11—C12178.1 (5)C217—C210—C211—C216121.2 (4)
C17—C10—C11—C1259.4 (7)C218—C210—C211—C216115.2 (5)
C18—C10—C11—C1265.2 (7)C216—C211—C212—C2131.5 (8)
C16—C11—C12—C133.1 (7)C210—C211—C212—C213175.6 (5)
C10—C11—C12—C13179.4 (5)C211—C212—C213—C2141.4 (8)
C11—C12—C13—C143.3 (8)C212—C213—C214—C2151.4 (8)
C12—C13—C14—C152.2 (8)C213—C214—C215—C2161.4 (8)
C13—C14—C15—C160.8 (7)C212—C211—C216—C2151.7 (7)
C14—C15—C16—C110.7 (7)C210—C211—C216—C215176.9 (4)
C14—C15—C16—N3179.0 (4)C212—C211—C216—N203178.7 (4)
C12—C11—C16—C151.9 (7)C210—C211—C216—N2033.4 (5)
C10—C11—C16—C15179.8 (4)C214—C215—C216—C2111.6 (7)
C12—C11—C16—N3179.5 (4)C214—C215—C216—N203178.8 (4)
C10—C11—C16—N31.5 (5)C209—N203—C216—C2114.0 (5)
C9—N3—C16—C15179.3 (5)C219—N203—C216—C211175.7 (4)
C19—N3—C16—C151.3 (7)C209—N203—C216—C215176.4 (5)
C9—N3—C16—C112.2 (5)C219—N203—C216—C2154.7 (7)
C19—N3—C16—C11179.9 (4)C209—N203—C219—C22090.9 (6)
C9—N3—C19—C2084.7 (6)C216—N203—C219—C22079.3 (5)
C16—N3—C19—C2092.9 (5)N203—C219—C220—O20364.6 (6)
N3—C19—C20—O365.3 (5)C307—N301—N302—C308178.5 (4)
C107—N101—N102—C108177.1 (4)O301—C301—C302—C303179.3 (5)
O101—C101—C102—C103179.0 (5)O302—C301—C302—C3034.8 (6)
O102—C101—C102—C1032.0 (7)O301—C301—C302—C3070.4 (7)
O101—C101—C102—C1071.1 (8)O302—C301—C302—C307174.0 (4)
O102—C101—C102—C107178.0 (4)C307—C302—C303—C3043.4 (7)
C107—C102—C103—C1040.4 (7)C301—C302—C303—C304175.5 (5)
C101—C102—C103—C104179.5 (4)C302—C303—C304—C3051.3 (8)
C102—C103—C104—C1052.4 (7)C303—C304—C305—C3063.1 (8)
C103—C104—C105—C1062.7 (8)C304—C305—C306—C3070.2 (8)
C104—C105—C106—C1070.3 (8)C305—C306—C307—C3024.6 (7)
N102—N101—C107—C1069.5 (7)C305—C306—C307—N301176.7 (5)
N102—N101—C107—C102170.5 (4)C303—C302—C307—C3066.3 (7)
C105—C106—C107—N101177.5 (5)C301—C302—C307—C306172.6 (4)
C105—C106—C107—C1022.5 (7)C303—C302—C307—N301175.0 (4)
C103—C102—C107—N101177.2 (4)C301—C302—C307—N3016.1 (7)
C101—C102—C107—N1012.9 (7)N302—N301—C307—C30610.7 (6)
C103—C102—C107—C1062.8 (7)N302—N301—C307—C302170.6 (4)
C101—C102—C107—C106177.2 (4)N301—N302—C308—C309180.0 (4)
N101—N102—C108—C109178.7 (4)C316—N303—C309—C308178.1 (4)
C116—N103—C109—C108179.7 (4)C39—N303—C309—C3086.1 (7)
C119—N103—C109—C1088.2 (7)C316—N303—C309—C3102.0 (5)
C116—N103—C109—C1100.4 (5)C39—N303—C309—C310174.0 (4)
C119—N103—C109—C110172.6 (4)N302—C308—C309—N303176.3 (4)
N102—C108—C109—N103177.8 (4)N302—C308—C309—C3103.8 (7)
N102—C108—C109—C1103.1 (7)N303—C309—C310—C3111.4 (5)
N103—C109—C110—C1110.2 (5)C308—C309—C310—C311178.8 (4)
C108—C109—C110—C111179.4 (4)N303—C309—C310—C317118.1 (4)
N103—C109—C110—C118117.7 (4)C308—C309—C310—C31761.8 (6)
C108—C109—C110—C11863.1 (6)N303—C309—C310—C318118.4 (4)
N103—C109—C110—C117118.8 (4)C308—C309—C310—C31861.7 (6)
C108—C109—C110—C11760.4 (6)C317—C310—C311—C31262.6 (7)
C109—C110—C111—C112177.8 (5)C309—C310—C311—C312178.7 (5)
C118—C110—C111—C11260.7 (7)C318—C310—C311—C31261.9 (6)
C117—C110—C111—C11263.6 (6)C317—C310—C311—C316118.4 (4)
C109—C110—C111—C1160.0 (5)C309—C310—C311—C3160.3 (5)
C118—C110—C111—C116117.1 (4)C318—C310—C311—C316117.1 (4)
C117—C110—C111—C116118.6 (4)C316—C311—C312—C3130.0 (8)
C116—C111—C112—C1131.5 (7)C310—C311—C312—C313179.0 (5)
C110—C111—C112—C113179.1 (5)C311—C312—C313—C3140.3 (8)
C111—C112—C113—C1140.8 (8)C312—C313—C314—C3150.4 (8)
C112—C113—C114—C1150.0 (8)C313—C314—C315—C3161.3 (8)
C113—C114—C115—C1160.1 (7)C314—C315—C316—C3111.6 (7)
C112—C111—C116—C1151.5 (7)C314—C315—C316—N303179.6 (5)
C110—C111—C116—C115179.6 (4)C312—C311—C316—C3150.9 (8)
C112—C111—C116—N103178.4 (4)C310—C311—C316—C315178.2 (4)
C110—C111—C116—N1030.3 (5)C312—C311—C316—N303180.0 (4)
C114—C115—C116—C1110.7 (7)C310—C311—C316—N3030.8 (5)
C114—C115—C116—N103179.1 (4)C309—N303—C316—C315177.1 (5)
C109—N103—C116—C1110.4 (5)C39—N303—C316—C3154.5 (7)
C119—N103—C116—C111172.9 (4)C309—N303—C316—C3111.8 (5)
C109—N103—C116—C115179.4 (5)C39—N303—C316—C311174.4 (4)
C119—N103—C116—C1157.0 (7)N103—C119—C12A—O13A64.2 (19)
C109—N103—C119—C12A88.8 (12)C12B—C119—C12A—O13A122 (18)
C116—N103—C119—C12A82.4 (12)C309—N303—C39—C32A88.8 (8)
C109—N103—C119—C12B82.7 (11)C316—N303—C39—C32A82.6 (7)
C116—N103—C119—C12B88.5 (11)N303—C39—C32A—O32A154.6 (10)
C207—N201—N202—C208178.7 (4)N103—C119—C12B—O13B61.0 (18)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
O32A—H3A0···O1010.841.942.644 (8)140
O2—H2O···O140.841.662.457 (5)158
N1—H1N···O10.70 (5)2.08 (5)2.652 (5)139 (6)
O3—H3O···O13i0.841.972.792 (5)165
N101—H11N···O1010.97 (5)1.90 (5)2.642 (6)132 (4)
N201—H21N···O2010.90 (5)1.89 (6)2.626 (6)138 (5)
O203—H23O···O701ii0.841.952.741 (6)157
N301—H31N···O3010.96 (5)1.95 (5)2.654 (5)129 (4)
O102—H102···O21iii0.841.682.509 (5)169
O202—H202···O13iv0.841.812.565 (5)149
O302—H302···O22v0.841.772.562 (6)157
C8—H8···O11vi0.952.553.402 (6)150
C12B—H12C···O3010.992.413.37 (2)164
C15—H15···O12i0.952.293.143 (6)149
C19—H19B···O11vi0.992.393.357 (7)166
C20—H20B···O201vi0.992.413.343 (6)157
C218—H21E···O13B0.982.443.193 (8)133
C219—H21H···O10.992.413.072 (6)124
C220—H22B···O1vi0.992.483.456 (6)168
C39—H39A···O101iii0.992.553.248 (6)128
C39—H39B···O230.992.533.514 (7)175
C108—H108···O240.952.263.073 (6)143
C114—H114···O102vii0.952.543.323 (7)139
C115—H115···O23v0.952.393.202 (7)143
C205—H205···O21v0.952.573.359 (7)141
C208—H208···O120.952.263.119 (5)150
C212—H212···O80A0.952.603.486 (10)156
C215—H215···O11vi0.952.273.137 (7)152
C306—H306···O203viii0.952.363.154 (7)140
C308—H308···O230.952.393.278 (6)155
C315—H315···O24iii0.952.263.150 (6)156
Symmetry codes: (i) x, y+1, z; (ii) x1, y, z; (iii) x+1, y+1, z+1; (iv) x, y, z; (v) x+1, y, z+1; (vi) x, y+1, z; (vii) x, y1, z; (viii) x+1, y, z.

Experimental details

Crystal data
Chemical formula2C20H22N3O3+·SO42·H2O
Mr816.88
Crystal system, space groupTriclinic, P1
Temperature (K)153
a, b, c (Å)12.2530 (9), 14.6114 (3), 23.2442 (4)
α, β, γ (°)71.681 (1), 87.688 (2), 82.627 (7)
V3)3917.9 (3)
Z4
Radiation typeCu Kα
µ (mm1)1.33
Crystal size (mm)0.68 × 0.40 × 0.24
Data collection
DiffractometerRigaku Spider
diffractometer
Absorption correctionMulti-scan
(ABSCOR; Higashi, 1995)
Tmin, Tmax0.66, 1.0
No. of measured, independent and
observed [I > 2σ(I)] reflections
24005, 10558, 9283
Rint0.044
θmax (°)58.9
(sin θ/λ)max1)0.556
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.053, 0.152, 1.10
No. of reflections10558
No. of parameters1069
No. of restraints2
H-atom treatmentH atoms treated by a mixture of independent and constrained refinement
Δρmax, Δρmin (e Å3)0.52, 0.53

Computer programs: CrystalClear (Rigaku, 2005), FSProcess in PROCESS-AUTO (Rigaku, 1998), SHELXS97 (Sheldrick, 2008), WinGX (Farrugia, 2012) and Mercury (Macrae et al., 2008), SHELXL97 (Sheldrick, 2008) and PLATON (Spek, 2009).

Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
O32A—H3A0···O1010.841.942.644 (8)140
O2—H2O···O140.841.662.457 (5)158
N1—H1N···O10.70 (5)2.08 (5)2.652 (5)139 (6)
O3—H3O···O13i0.841.972.792 (5)165
N101—H11N···O1010.97 (5)1.90 (5)2.642 (6)132 (4)
N201—H21N···O2010.90 (5)1.89 (6)2.626 (6)138 (5)
O203—H23O···O701ii0.841.952.741 (6)157
N301—H31N···O3010.96 (5)1.95 (5)2.654 (5)129 (4)
O102—H102···O21iii0.841.682.509 (5)169
O202—H202···O13iv0.841.812.565 (5)149
O302—H302···O22v0.841.772.562 (6)157
C8—H8···O11vi0.952.553.402 (6)150
C12B—H12C···O3010.992.413.37 (2)164
C15—H15···O12i0.952.293.143 (6)149
C19—H19B···O11vi0.992.393.357 (7)166
C20—H20B···O201vi0.992.413.343 (6)157
C220—H22B···O1vi0.992.483.456 (6)168
C39—H39B···O230.992.533.514 (7)175
C108—H108···O240.952.263.073 (6)143
C114—H114···O102vii0.952.543.323 (7)139
C115—H115···O23v0.952.393.202 (7)143
C205—H205···O21v0.952.573.359 (7)141
C208—H208···O120.952.263.119 (5)150
C212—H212···O80A0.952.603.486 (10)156
C215—H215···O11vi0.952.273.137 (7)152
C306—H306···O203viii0.952.363.154 (7)140
C308—H308···O230.952.393.278 (6)155
C315—H315···O24iii0.952.263.150 (6)156
Symmetry codes: (i) x, y+1, z; (ii) x1, y, z; (iii) x+1, y+1, z+1; (iv) x, y, z; (v) x+1, y, z+1; (vi) x, y+1, z; (vii) x, y1, z; (viii) x+1, y, z.
 

Acknowledgements

We thank the MacDiarmid Institute for Advanced Materials and Nanotechnology for funding of the diffractometer equipment and the NZ Foundation for Research, Science & Technology for funding.

References

First citationBernstein, J., Davis, R. E., Shimoni, L. & Chang, N.-L. (1995). Angew. Chem. Int. Ed. Engl. 34, 1555–1573.  CrossRef CAS Web of Science
First citationBhuiyan, M., Delower, H., Ashraf, M., Teshome, A., Gainsford, G. J., Kay, A. J., Asselberghs, I. & Clays, K. (2011). Dyes Pigm. 89, 177–187.  Web of Science CSD CrossRef CAS
First citationFarrugia, L. J. (2012). J. Appl. Cryst. 45, 849–854.  Web of Science CrossRef CAS IUCr Journals
First citationGainsford, G. J., Ashraf, M. & Kay, A. J. (2013). Unpublished work.
First citationHigashi, T. (1995). ABSCOR. Rigaku Corporation, Tokyo, Japan.
First citationMacrae, C. F., Bruno, I. J., Chisholm, J. A., Edgington, P. R., McCabe, P., Pidcock, E., Rodriguez-Monge, L., Taylor, R., van de Streek, J. & Wood, P. A. (2008). J. Appl. Cryst. 41, 466–470.  Web of Science CrossRef CAS IUCr Journals
First citationRigaku (1998). PROCESS-AUTO. Rigaku Corporation, Tokyo, Japan.
First citationRigaku (2005). CrystalClear. Rigaku Americas Corporation, The Woodlands, Texas, USA.
First citationSheldrick, G. M. (2008). Acta Cryst. A64, 112–122.  Web of Science CrossRef CAS IUCr Journals
First citationSpek, A. L. (2009). Acta Cryst. D65, 148–155.  Web of Science CrossRef CAS IUCr Journals

This is an open-access article distributed under the terms of the Creative Commons Attribution (CC-BY) Licence, which permits unrestricted use, distribution, and reproduction in any medium, provided the original authors and source are cited.

Journal logoCRYSTALLOGRAPHIC
COMMUNICATIONS
ISSN: 2056-9890
Volume 69| Part 3| March 2013| Pages o343-o344
Follow Acta Cryst. E
Sign up for e-alerts
Follow Acta Cryst. on Twitter
Follow us on facebook
Sign up for RSS feeds