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The 1:1 adduct of piperazine and ethane-1,2-diphosphonic acid is a salt [C4H12N2]2+·[C2H6O6P2]2−, in which both ions lie across centres of inversion in space group P21/c. The anions are linked by a single type of O—H...O hydrogen bond [O...O, 2.562 (3) Å; H...O, 1.73 Å, O—H...O, 169°] into (6, 3) nets built from a single type of R^4_4(22) ring. The cations lie between these nets, linked to them by two types of N—H...O hydrogen bond [N...O, 2.635 (3) and 2.735 (3) Å; H...O 1.72 and 1.82 Å, N—H...O, 175 and 177°] such that the cations link adjacent sheets, thus forming a pillared-layer framework. The aquated adduct formed between trimethylenedipiperidine and ethane-1,2-diphosphonic acid is also a salt [C13H28N2]2+·[C2H6O6P2]2−·2.8[H2O], in which there are 12 different types of hydrogen bond, eight O—H...O and four N—H...O. The anions are linked into chains by pairs of O—H...O hydrogen bonds and these chains are linked by the water molecules into a continuous three-dimensional framework. Within the anion/water framework are large voids which contain pairs of cations, linked to the framework by N—H...O hydrogen bonds.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S0108768100014841/na0111sup1.cif
Contains datablocks global, 18, 17

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S0108768100014841/na011118sup2.hkl
Contains datablock 18

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S0108768100014841/na011117sup3.hkl
Contains datablock 17

CCDC references: 159972; 159973

Comment top

In full text version

Experimental top

In full text version

Refinement top

In full text version

Computing details top

For both compounds, data collection: Kappa-CCD server software (Nonius, 1997); cell refinement: DENZO-SMN (Otwinowski & Minor, 1997); data reduction: DENZO-SMN (Otwinowski & Minor, 1997); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997a); program(s) used to refine structure: NRCVAX96 and SHELXL97 (Sheldrick, 1997b); molecular graphics: NRCVAX96, ORTEP (Johnson, 1976), PLATON (Spek, 2000); software used to prepare material for publication: NRCVAX96, SHELXL97 and WORDPERFECT macro PRPKAPPA (Ferguson, 1999).

Figures top
[Figure 1]
[Figure 2]
[Figure 3]
[Figure 4]
[Figure 5]
[Figure 6]
[Figure 7]
In full text version
(18) Piperazine-ethane-1,2-diphosphonic acid (1/1) top
Crystal data top
C4H12N2·C2H6O6P2F(000) = 292
Mr = 276.16Dx = 1.488 Mg m3
Monoclinic, P21/cMo Kα radiation, λ = 0.71073 Å
a = 7.3914 (6) ÅCell parameters from 3237 reflections
b = 9.3343 (7) Åθ = 2.9–27.4°
c = 9.3590 (6) ŵ = 0.37 mm1
β = 107.291 (4)°T = 150 K
V = 616.53 (8) Å3Needle, colourless
Z = 20.20 × 0.06 × 0.02 mm
Data collection top
Kappa-CCD
diffractometer
1401 independent reflections
Radiation source: fine-focus sealed X-ray tube947 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.057
ϕ scans and ω scans with κ offsetsθmax = 27.4°, θmin = 2.9°
Absorption correction: multi-scan
DENZO-SMN (Otwinowski & Minor, 1997)
h = 09
Tmin = 0.930, Tmax = 0.993k = 012
3237 measured reflectionsl = 1211
Refinement top
Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.059Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.123H-atom parameters constrained
S = 1.04 w = 1/[σ2(Fo2) + (0.0312P)2 + 0.6688P]
where P = (Fo2 + 2Fc2)/3
1401 reflections(Δ/σ)max < 0.001
74 parametersΔρmax = 0.37 e Å3
0 restraintsΔρmin = 0.43 e Å3
Crystal data top
C4H12N2·C2H6O6P2V = 616.53 (8) Å3
Mr = 276.16Z = 2
Monoclinic, P21/cMo Kα radiation
a = 7.3914 (6) ŵ = 0.37 mm1
b = 9.3343 (7) ÅT = 150 K
c = 9.3590 (6) Å0.20 × 0.06 × 0.02 mm
β = 107.291 (4)°
Data collection top
Kappa-CCD
diffractometer
1401 independent reflections
Absorption correction: multi-scan
DENZO-SMN (Otwinowski & Minor, 1997)
947 reflections with I > 2σ(I)
Tmin = 0.930, Tmax = 0.993Rint = 0.057
3237 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0590 restraints
wR(F2) = 0.123H-atom parameters constrained
S = 1.04Δρmax = 0.37 e Å3
1401 reflectionsΔρmin = 0.43 e Å3
74 parameters
Special details top

Experimental. The program DENZO-SMN (Otwinowski & Minor, 1997) uses a scaling algorithm (Fox & Holmes, 1966) which effectively corrects for absorption effects. High redundancy data were used in the scaling program hence the 'multi-scan' code word was used. No transmission coefficients are available from the program (only scale factors for each frame). The scale factors in the experimental table are calculated from the 'size' command in the SHELXL97 input file.

Geometry. Mean-plane data from the final SHELXL97 refinement run:-

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
P10.94421 (13)0.41065 (9)0.20303 (9)0.0164 (3)
O10.7583 (3)0.3578 (2)0.2177 (2)0.0206 (6)
O21.0375 (3)0.5304 (2)0.3082 (2)0.0205 (6)
O31.0943 (3)0.2861 (2)0.2286 (3)0.0220 (6)
C10.9100 (4)0.4705 (4)0.0138 (3)0.0204 (8)
N10.6521 (4)0.4553 (3)0.4446 (3)0.0208 (7)
C20.5123 (5)0.3499 (4)0.4674 (4)0.0219 (8)
C30.5674 (5)0.5999 (4)0.4102 (4)0.0236 (8)
H31.03790.20690.21180.033*
H1A0.86260.38920.05510.024*
H1B0.81150.54600.01020.024*
H1C0.75400.45970.52960.025*
H1D0.69540.42510.36700.025*
H2A0.57460.25570.49490.026*
H2B0.40810.33810.37310.026*
H3A0.46520.59720.31390.028*
H3B0.66530.66820.40000.028*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
P10.0180 (5)0.0168 (5)0.0148 (4)0.0004 (4)0.0053 (3)0.0008 (4)
O10.0195 (13)0.0258 (13)0.0191 (12)0.0030 (11)0.0095 (10)0.0028 (10)
O20.0240 (14)0.0151 (12)0.0191 (11)0.0036 (10)0.0013 (10)0.0046 (10)
O30.0212 (14)0.0114 (12)0.0330 (13)0.0015 (10)0.0074 (11)0.0018 (11)
C10.0202 (19)0.025 (2)0.0157 (16)0.0028 (16)0.0047 (14)0.0001 (14)
N10.0199 (16)0.0273 (17)0.0162 (14)0.0013 (13)0.0069 (12)0.0021 (12)
C20.0227 (19)0.0210 (18)0.0219 (17)0.0010 (16)0.0064 (15)0.0019 (15)
C30.025 (2)0.026 (2)0.0214 (17)0.0006 (17)0.0095 (15)0.0038 (15)
Geometric parameters (Å, º) top
P1—O11.504 (2)N1—C21.487 (4)
P1—O21.514 (2)N1—H1C0.9200
P1—O31.575 (2)N1—H1D0.9200
P1—C11.802 (3)C2—C3ii1.510 (5)
O3—H30.8400C2—H2A0.9900
C1—C1i1.531 (6)C2—H2B0.9900
C1—H1A0.9900C3—C2ii1.510 (5)
C1—H1B0.9900C3—H3A0.9900
N1—C31.482 (4)C3—H3B0.9900
O1—P1—O2115.77 (13)C3—N1—H1D109.3
O1—P1—O3111.42 (13)C2—N1—H1D109.3
O2—P1—O3106.39 (13)H1C—N1—H1D108.0
O1—P1—C1109.04 (13)N1—C2—C3ii110.4 (3)
O2—P1—C1108.31 (14)N1—C2—H2A109.6
O3—P1—C1105.36 (15)C3ii—C2—H2A109.6
P1—O3—H3109.5N1—C2—H2B109.6
C1i—C1—P1113.7 (3)C3ii—C2—H2B109.6
C1i—C1—H1A108.8H2A—C2—H2B108.1
P1—C1—H1A108.8N1—C3—C2ii110.7 (3)
C1i—C1—H1B108.8N1—C3—H3A109.5
P1—C1—H1B108.8C2ii—C3—H3A109.5
H1A—C1—H1B107.7N1—C3—H3B109.5
C3—N1—C2111.5 (3)C2ii—C3—H3B109.5
C3—N1—H1C109.3H3A—C3—H3B108.1
C2—N1—H1C109.3
O1—P1—C1—C1i178.9 (3)C3—N1—C2—C3ii56.5 (4)
O2—P1—C1—C1i52.1 (4)C2—N1—C3—C2ii56.7 (4)
O3—P1—C1—C1i61.4 (4)
Symmetry codes: (i) x+2, y+1, z; (ii) x+1, y+1, z+1.
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
O3—H3···O2iii0.841.732.562 (2)169
N1—H1C···O2iv0.921.822.735 (3)177
N1—H1D···O10.921.722.635 (3)175
C2—H2A···O1v0.992.373.166 (4)136
C2—H2B···O3vi0.992.363.285 (5)155
Symmetry codes: (iii) x+2, y1/2, z+1/2; (iv) x+2, y+1, z+1; (v) x, y+1/2, z+1/2; (vi) x1, y, z.
(17) 4,4'-trimethylenedipiperidine-ethane-1,2-diphosphonic acid-water (1/1/2.8). top
Crystal data top
(C13H28N2)·(C2H6O6P2)·2.8(H2O)F(000) = 973
Mr = 450.01Dx = 1.332 Mg m3
Monoclinic, P21/cMo Kα radiation, λ = 0.71073 Å
a = 6.1218 (2) ÅCell parameters from 13672 reflections
b = 20.6215 (7) Åθ = 3.0–30.1°
c = 18.1831 (7) ŵ = 0.24 mm1
β = 99.942 (2)°T = 120 K
V = 2260.98 (14) Å3Block, colourless
Z = 40.30 × 0.12 × 0.12 mm
Data collection top
Kappa-CCD
diffractometer
6599 independent reflections
Radiation source: fine-focus sealed X-ray tube4617 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.033
ϕ scans and ω scans with κ offsetsθmax = 30.1°, θmin = 3.0°
Absorption correction: multi-scan
DENZO-SMN (Otwinowski & Minor, 1997)
h = 08
Tmin = 0.932, Tmax = 0.972k = 290
13672 measured reflectionsl = 2524
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)] = 0.051Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.114H-atom parameters constrained
S = 1.02 w = 1/[σ2(Fo2) + (0.0333P)2 + 1.181P]
where P = (Fo2 + 2Fc2)/3
6599 reflections(Δ/σ)max = 0.001
284 parametersΔρmax = 0.40 e Å3
6 restraintsΔρmin = 0.39 e Å3
Crystal data top
(C13H28N2)·(C2H6O6P2)·2.8(H2O)V = 2260.98 (14) Å3
Mr = 450.01Z = 4
Monoclinic, P21/cMo Kα radiation
a = 6.1218 (2) ŵ = 0.24 mm1
b = 20.6215 (7) ÅT = 120 K
c = 18.1831 (7) Å0.30 × 0.12 × 0.12 mm
β = 99.942 (2)°
Data collection top
Kappa-CCD
diffractometer
6599 independent reflections
Absorption correction: multi-scan
DENZO-SMN (Otwinowski & Minor, 1997)
4617 reflections with I > 2σ(I)
Tmin = 0.932, Tmax = 0.972Rint = 0.033
13672 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0516 restraints
wR(F2) = 0.114H-atom parameters constrained
S = 1.02Δρmax = 0.40 e Å3
6599 reflectionsΔρmin = 0.39 e Å3
284 parameters
Special details top

Experimental. The program DENZO-SMN (Otwinowski & Minor, 1997) uses a scaling algorithm (Fox & Holmes, 1966) which effectively corrects for absorption effects. High redundancy data were used in the scaling program hence the 'multi-scan' code word was used. No transmission coefficients are available from the program (only scale factors for each frame). The scale factors in the experimental table are calculated from the 'size' command in the SHELXL97 input file.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/UeqOcc. (<1)
N110.2398 (2)0.26517 (8)0.50540 (9)0.0190 (3)
C120.1348 (3)0.33055 (10)0.50280 (12)0.0246 (4)
C130.3078 (3)0.38363 (9)0.50220 (12)0.0231 (4)
C140.4954 (3)0.37781 (9)0.56953 (11)0.0197 (4)
C150.5957 (3)0.30998 (9)0.56861 (11)0.0198 (4)
C160.4226 (3)0.25759 (10)0.57085 (11)0.0218 (4)
C170.6671 (3)0.43166 (9)0.57012 (11)0.0227 (4)
C180.8409 (3)0.43454 (9)0.64141 (11)0.0231 (4)
C190.9987 (3)0.49186 (9)0.64262 (11)0.0225 (4)
N211.4015 (2)0.56843 (7)0.84112 (9)0.0196 (3)
C221.2669 (3)0.50973 (9)0.85170 (11)0.0213 (4)
C231.0895 (3)0.50044 (10)0.78325 (11)0.0219 (4)
C241.1834 (3)0.49508 (9)0.71087 (11)0.0198 (4)
C251.3363 (3)0.55287 (9)0.70467 (11)0.0218 (4)
C261.5105 (3)0.56218 (10)0.77452 (11)0.0227 (4)
P10.51784 (7)0.18672 (2)0.36067 (3)0.01750 (11)
P20.97414 (7)0.28310 (2)0.22866 (3)0.01652 (11)
O110.5704 (2)0.13972 (7)0.42480 (8)0.0251 (3)
O120.4089 (2)0.24934 (6)0.37945 (7)0.0201 (3)
O130.3689 (2)0.15207 (6)0.29305 (8)0.0231 (3)
O210.8935 (2)0.33129 (6)0.16740 (7)0.0220 (3)
O221.0973 (2)0.22498 (6)0.20657 (7)0.0194 (3)
O231.1228 (2)0.32169 (6)0.29441 (8)0.0221 (3)
C10.7729 (3)0.20749 (9)0.32879 (10)0.0197 (4)
C20.7328 (3)0.25730 (9)0.26563 (11)0.0189 (4)
O30.3198 (2)0.08832 (8)0.52162 (8)0.0274 (3)
O40.0510 (4)0.16833 (16)0.52524 (9)0.0251 (8)0.866 (11)
O410.122 (3)0.1948 (8)0.5260 (6)0.017 (4)*0.134 (11)
O50.1802 (7)0.02668 (15)0.5826 (3)0.0366 (14)0.585 (10)
O510.1100 (16)0.0376 (4)0.5439 (7)0.030 (3)*0.209 (11)
H11A0.29560.25860.46220.023*
H11B0.13360.23400.50780.023*
H12A0.06150.33620.54680.030*
H12B0.02010.33410.45740.030*
H13A0.23600.42660.50300.028*
H13B0.37030.38050.45560.028*
H140.42920.38200.61590.024*
H15A0.66120.30470.52280.024*
H15B0.71600.30500.61220.024*
H16A0.49150.21430.56950.026*
H16B0.36190.26110.61780.026*
H17A0.58890.47380.56350.027*
H17B0.74390.42540.52700.027*
H18A0.76450.43750.68500.028*
H18B0.92800.39380.64610.028*
H19A0.91120.53240.64020.027*
H19B1.06740.49000.59720.027*
H21A1.31110.60440.83580.023*
H21B1.50810.57440.88290.023*
H22A1.19690.51520.89650.026*
H22B1.36400.47100.85920.026*
H23A0.98540.53750.77920.026*
H23B1.00460.46060.78970.026*
H241.27310.45440.71280.024*
H25A1.41170.54630.66130.026*
H25B1.24560.59280.69560.026*
H26A1.61270.52460.78090.027*
H26B1.59840.60170.76920.027*
H130.28290.17930.26880.035*
H231.21580.29640.31870.033*
H1A0.87990.22540.37100.024*
H1B0.83870.16780.31100.024*
H2A0.66350.29610.28400.023*
H2B0.62460.23880.22420.023*
H310.197 (2)0.1081 (10)0.5193 (14)0.040*
H320.380 (3)0.1032 (11)0.4864 (9)0.040*
H410.173 (3)0.1595 (14)0.4967 (13)0.040*0.866 (11)
H420.066 (5)0.1721 (14)0.5706 (5)0.040*0.866 (11)
H510.206 (7)0.0030 (18)0.5468 (18)0.040*0.585 (10)
H520.244 (6)0.0617 (11)0.574 (2)0.040*0.585 (10)
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
N110.0165 (7)0.0241 (8)0.0165 (8)0.0035 (6)0.0031 (6)0.0025 (6)
C120.0163 (8)0.0299 (11)0.0262 (11)0.0021 (8)0.0005 (8)0.0052 (9)
C130.0205 (9)0.0211 (10)0.0256 (11)0.0027 (7)0.0021 (8)0.0015 (8)
C140.0180 (8)0.0232 (10)0.0174 (9)0.0004 (7)0.0012 (7)0.0031 (8)
C150.0162 (8)0.0220 (10)0.0199 (9)0.0013 (7)0.0002 (7)0.0026 (8)
C160.0205 (9)0.0265 (10)0.0176 (10)0.0035 (8)0.0012 (7)0.0037 (8)
C170.0246 (9)0.0191 (9)0.0224 (10)0.0012 (8)0.0019 (8)0.0021 (8)
C180.0238 (9)0.0224 (10)0.0212 (10)0.0014 (8)0.0010 (8)0.0020 (8)
C190.0250 (9)0.0207 (10)0.0206 (10)0.0024 (8)0.0007 (8)0.0008 (8)
N210.0160 (7)0.0205 (8)0.0209 (8)0.0017 (6)0.0005 (6)0.0012 (7)
C220.0210 (9)0.0227 (10)0.0198 (10)0.0022 (7)0.0023 (7)0.0006 (8)
C230.0156 (8)0.0268 (10)0.0223 (10)0.0027 (7)0.0005 (7)0.0003 (8)
C240.0184 (8)0.0190 (9)0.0213 (10)0.0002 (7)0.0014 (7)0.0023 (8)
C250.0227 (9)0.0216 (10)0.0218 (10)0.0042 (8)0.0064 (8)0.0034 (8)
C260.0173 (8)0.0238 (10)0.0277 (11)0.0032 (7)0.0063 (8)0.0033 (8)
P10.0165 (2)0.0196 (2)0.0159 (2)0.00030 (18)0.00156 (17)0.00276 (19)
P20.0166 (2)0.0180 (2)0.0150 (2)0.00223 (18)0.00275 (17)0.00145 (19)
O110.0200 (6)0.0305 (8)0.0240 (8)0.0005 (6)0.0012 (6)0.0115 (6)
O120.0204 (6)0.0237 (7)0.0162 (7)0.0024 (5)0.0031 (5)0.0007 (5)
O130.0244 (7)0.0176 (7)0.0242 (8)0.0010 (5)0.0047 (6)0.0003 (6)
O210.0240 (6)0.0241 (7)0.0185 (7)0.0069 (5)0.0059 (5)0.0053 (5)
O220.0201 (6)0.0208 (7)0.0171 (7)0.0040 (5)0.0030 (5)0.0002 (5)
O230.0234 (7)0.0196 (7)0.0216 (7)0.0017 (5)0.0013 (6)0.0003 (6)
C10.0186 (8)0.0231 (10)0.0174 (9)0.0023 (7)0.0025 (7)0.0023 (8)
C20.0159 (8)0.0224 (10)0.0179 (9)0.0014 (7)0.0018 (7)0.0025 (8)
O30.0221 (7)0.0372 (9)0.0227 (8)0.0027 (6)0.0033 (6)0.0068 (7)
O40.0207 (11)0.0370 (17)0.0174 (9)0.0077 (11)0.0026 (7)0.0007 (8)
O50.040 (2)0.0316 (18)0.043 (3)0.0086 (13)0.0215 (19)0.0061 (15)
Geometric parameters (Å, º) top
N11—C121.491 (2)C23—H23B0.9900
N11—C161.494 (2)C24—C251.532 (3)
N11—H11A0.9200C24—H241.0000
N11—H11B0.9200C25—C261.523 (3)
C12—C131.524 (3)C25—H25A0.9900
C12—H12A0.9900C25—H25B0.9900
C12—H12B0.9900C26—H26A0.9900
C13—C141.532 (2)C26—H26B0.9900
C13—H13A0.9900P1—O111.5076 (14)
C13—H13B0.9900P1—O121.5189 (14)
C14—C171.528 (3)P1—O131.5707 (13)
C14—C151.529 (3)P1—C11.8086 (19)
C14—H141.0000P2—O221.5071 (13)
C15—C161.519 (2)P2—O211.5105 (13)
C15—H15A0.9900P2—O231.5860 (13)
C15—H15B0.9900P2—C21.8055 (18)
C16—H16A0.9900O13—H130.8400
C16—H16B0.9900O23—H230.8400
C17—C181.530 (3)C1—C21.529 (3)
C17—H17A0.9900C1—H1A0.9900
C17—H17B0.9900C1—H1B0.9900
C18—C191.524 (3)C2—H2A0.9900
C18—H18A0.9900C2—H2B0.9900
C18—H18B0.9900O3—H310.85 (2)
C19—C241.529 (2)O3—H320.85 (2)
C19—H19A0.9900O4—O410.701 (18)
C19—H19B0.9900O4—H410.850 (3)
N21—C261.486 (2)O4—H420.850 (3)
N21—C221.495 (2)O41—H410.92 (2)
N21—H21A0.9200O41—H420.95 (2)
N21—H21B0.9200O5—O510.791 (10)
C22—C231.516 (3)O5—H510.850 (3)
C22—H22A0.9900O5—H520.850 (3)
C22—H22B0.9900O51—H510.92 (4)
C23—C241.528 (3)O51—H521.03 (3)
C23—H23A0.9900
C12—N11—C16112.30 (15)H22A—C22—H22B108.3
C12—N11—H11A109.1C22—C23—C24113.18 (15)
C16—N11—H11A109.1C22—C23—H23A108.9
C12—N11—H11B109.1C24—C23—H23A108.9
C16—N11—H11B109.1C22—C23—H23B108.9
H11A—N11—H11B107.9C24—C23—H23B108.9
N11—C12—C13110.69 (15)H23A—C23—H23B107.8
N11—C12—H12A109.5C23—C24—C19111.52 (15)
C13—C12—H12A109.5C23—C24—C25109.42 (15)
N11—C12—H12B109.5C19—C24—C25110.47 (16)
C13—C12—H12B109.5C23—C24—H24108.5
H12A—C12—H12B108.1C19—C24—H24108.5
C12—C13—C14111.34 (16)C25—C24—H24108.5
C12—C13—H13A109.4C26—C25—C24112.68 (16)
C14—C13—H13A109.4C26—C25—H25A109.1
C12—C13—H13B109.4C24—C25—H25A109.1
C14—C13—H13B109.4C26—C25—H25B109.1
H13A—C13—H13B108.0C24—C25—H25B109.1
C17—C14—C15112.84 (15)H25A—C25—H25B107.8
C17—C14—C13111.63 (16)N21—C26—C25110.04 (15)
C15—C14—C13108.05 (15)N21—C26—H26A109.7
C17—C14—H14108.1C25—C26—H26A109.7
C15—C14—H14108.1N21—C26—H26B109.7
C13—C14—H14108.1C25—C26—H26B109.7
C16—C15—C14111.55 (15)H26A—C26—H26B108.2
C16—C15—H15A109.3O11—P1—O12114.59 (8)
C14—C15—H15A109.3O11—P1—O13109.30 (8)
C16—C15—H15B109.3O12—P1—O13110.17 (7)
C14—C15—H15B109.3O11—P1—C1108.62 (8)
H15A—C15—H15B108.0O12—P1—C1107.92 (8)
N11—C16—C15109.52 (15)O13—P1—C1105.87 (8)
N11—C16—H16A109.8O22—P2—O21116.20 (8)
C15—C16—H16A109.8O22—P2—O23110.58 (7)
N11—C16—H16B109.8O21—P2—O23107.33 (8)
C15—C16—H16B109.8O22—P2—C2110.12 (8)
H16A—C16—H16B108.2O21—P2—C2106.51 (8)
C14—C17—C18114.29 (16)O23—P2—C2105.50 (8)
C14—C17—H17A108.7P1—O13—H13109.5
C18—C17—H17A108.7P2—O23—H23109.5
C14—C17—H17B108.7C2—C1—P1111.37 (12)
C18—C17—H17B108.7C2—C1—H1A109.4
H17A—C17—H17B107.6P1—C1—H1A109.4
C19—C18—C17112.88 (16)C2—C1—H1B109.4
C19—C18—H18A109.0P1—C1—H1B109.4
C17—C18—H18A109.0H1A—C1—H1B108.0
C19—C18—H18B109.0C1—C2—P2116.24 (12)
C17—C18—H18B109.0C1—C2—H2A108.2
H18A—C18—H18B107.8P2—C2—H2A108.2
C18—C19—C24115.05 (16)C1—C2—H2B108.2
C18—C19—H19A108.5P2—C2—H2B108.2
C24—C19—H19A108.5H2A—C2—H2B107.4
C18—C19—H19B108.5H31—O3—H32107 (2)
C24—C19—H19B108.5O41—O4—H4172 (2)
H19A—C19—H19B107.5O41—O4—H4275 (2)
C26—N21—C22111.69 (15)H41—O4—H42112 (3)
C26—N21—H21A109.3O4—O41—H4161.3 (16)
C22—N21—H21A109.3O4—O41—H4259.8 (15)
C26—N21—H21B109.3H41—O41—H4298 (3)
C22—N21—H21B109.3O51—O5—H5168 (3)
H21A—N21—H21B107.9O51—O5—H5278 (3)
N21—C22—C23109.22 (15)H51—O5—H52101 (4)
N21—C22—H22A109.8O5—O51—H5158.9 (17)
C23—C22—H22A109.8O5—O51—H5253.8 (16)
N21—C22—H22B109.8H51—O51—H5284 (3)
C23—C22—H22B109.8
C16—N11—C12—C1356.4 (2)C22—C23—C24—C2552.4 (2)
N11—C12—C13—C1456.2 (2)C18—C19—C24—C2360.2 (2)
C12—C13—C14—C17178.88 (16)C18—C19—C24—C25177.84 (16)
C12—C13—C14—C1556.5 (2)C23—C24—C25—C2651.4 (2)
C17—C14—C15—C16177.95 (16)C19—C24—C25—C26174.59 (16)
C13—C14—C15—C1658.1 (2)C22—N21—C26—C2559.5 (2)
C12—N11—C16—C1557.2 (2)C24—C25—C26—N2155.5 (2)
C14—C15—C16—N1158.6 (2)O11—P1—C1—C2177.70 (13)
C15—C14—C17—C1866.4 (2)O12—P1—C1—C252.92 (15)
C13—C14—C17—C18171.71 (16)O13—P1—C1—C265.02 (15)
C14—C17—C18—C19175.63 (16)P1—C1—C2—P2179.53 (10)
C17—C18—C19—C24176.98 (17)O22—P2—C2—C152.81 (16)
C26—N21—C22—C2359.66 (19)O21—P2—C2—C1179.60 (14)
N21—C22—C23—C2456.5 (2)O23—P2—C2—C166.54 (16)
C22—C23—C24—C19174.92 (16)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
O13—H13···O22i0.841.742.568 (2)170
O23—H23···O12ii0.841.762.598 (2)173
O3—H31···O40.85 (2)1.98 (2)2.816 (3)168 (2)
O3—H32···O110.85 (2)1.91 (2)2.740 (2)167 (2)
O4—H41···O11i0.85 (2)1.91 (2)2.756 (3)174 (2)
O4—H42···O21iii0.85 (2)1.82 (2)2.665 (2)172 (3)
O5—H51···O30.85 (4)2.09 (4)2.813 (4)143 (3)
O5—H52···O11iv0.85 (3)1.97 (3)2.802 (4)168 (3)
N11—H11A···O120.921.772.691 (2)177
N11—H11B···O40.921.832.740 (3)172
N21—H21A···O21v0.921.822.732 (2)172
N21—H21B···O3vi0.921.892.800 (3)169
Symmetry codes: (i) x1, y, z; (ii) x+1, y, z; (iii) x1, y+1/2, z+1/2; (iv) x+1, y, z+1; (v) x+2, y+1, z+1; (vi) x+2, y+1/2, z+3/2.

Experimental details

(18)(17)
Crystal data
Chemical formulaC4H12N2·C2H6O6P2(C13H28N2)·(C2H6O6P2)·2.8(H2O)
Mr276.16450.01
Crystal system, space groupMonoclinic, P21/cMonoclinic, P21/c
Temperature (K)150120
a, b, c (Å)7.3914 (6), 9.3343 (7), 9.3590 (6)6.1218 (2), 20.6215 (7), 18.1831 (7)
β (°) 107.291 (4) 99.942 (2)
V3)616.53 (8)2260.98 (14)
Z24
Radiation typeMo KαMo Kα
µ (mm1)0.370.24
Crystal size (mm)0.20 × 0.06 × 0.020.30 × 0.12 × 0.12
Data collection
DiffractometerKappa-CCD
diffractometer
Kappa-CCD
diffractometer
Absorption correctionMulti-scan
DENZO-SMN (Otwinowski & Minor, 1997)
Multi-scan
DENZO-SMN (Otwinowski & Minor, 1997)
Tmin, Tmax0.930, 0.9930.932, 0.972
No. of measured, independent and
observed [I > 2σ(I)] reflections
3237, 1401, 947 13672, 6599, 4617
Rint0.0570.033
(sin θ/λ)max1)0.6470.705
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.059, 0.123, 1.04 0.051, 0.114, 1.02
No. of reflections14016599
No. of parameters74284
No. of restraints06
H-atom treatmentH-atom parameters constrainedH-atom parameters constrained
Δρmax, Δρmin (e Å3)0.37, 0.430.40, 0.39

Computer programs: Kappa-CCD server software (Nonius, 1997), DENZO-SMN (Otwinowski & Minor, 1997), SHELXS97 (Sheldrick, 1997a), NRCVAX96 and SHELXL97 (Sheldrick, 1997b), NRCVAX96, ORTEP (Johnson, 1976), PLATON (Spek, 2000), NRCVAX96, SHELXL97 and WORDPERFECT macro PRPKAPPA (Ferguson, 1999).

Hydrogen-bond geometry (Å, º) for (18) top
D—H···AD—HH···AD···AD—H···A
O3—H3···O2i0.841.732.562 (2)169
N1—H1C···O2ii0.921.822.735 (3)177
N1—H1D···O10.921.722.635 (3)175
C2—H2A···O1iii0.992.373.166 (4)136
C2—H2B···O3iv0.992.363.285 (5)155
Symmetry codes: (i) x+2, y1/2, z+1/2; (ii) x+2, y+1, z+1; (iii) x, y+1/2, z+1/2; (iv) x1, y, z.
Hydrogen-bond geometry (Å, º) for (17) top
D—H···AD—HH···AD···AD—H···A
O13—H13···O22i0.841.742.568 (2)170
O23—H23···O12ii0.841.762.598 (2)173
O3—H31···O40.85 (2)1.98 (2)2.816 (3)168 (2)
O3—H32···O110.85 (2)1.91 (2)2.740 (2)167 (2)
O4—H41···O11i0.85 (2)1.91 (2)2.756 (3)174 (2)
O4—H42···O21iii0.85 (2)1.82 (2)2.665 (2)172 (3)
O5—H51···O30.85 (4)2.09 (4)2.813 (4)143 (3)
O5—H52···O11iv0.85 (3)1.97 (3)2.802 (4)168 (3)
N11—H11A···O120.921.772.691 (2)177
N11—H11B···O40.921.832.740 (3)172
N21—H21A···O21v0.921.822.732 (2)172
N21—H21B···O3vi0.921.892.800 (3)169
Symmetry codes: (i) x1, y, z; (ii) x+1, y, z; (iii) x1, y+1/2, z+1/2; (iv) x+1, y, z+1; (v) x+2, y+1, z+1; (vi) x+2, y+1/2, z+3/2.
 

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