The title compound, sodium pamidronate monohydrate, Na
+·C
3H
10NO
7P
·H
2O, crystallizes in sheets in the
ab plane through Na-O coordination and hydrogen bonding to the pamidronate zwitterion. The neutral sheets are connected through hydrogen bonding, including the water molecule in the
c direction.
Supporting information
CCDC reference: 262266
Key indicators
- Single-crystal X-ray study
- T = 120 K
- Mean (C-C) = 0.003 Å
- R factor = 0.045
- wR factor = 0.111
- Data-to-parameter ratio = 17.6
checkCIF/PLATON results
No syntax errors found
Alert level C
PLAT042_ALERT_1_C Calc. and Rep. MoietyFormula Strings Differ .... ?
PLAT094_ALERT_2_C Ratio of Maximum / Minimum Residual Density .... 2.17
PLAT417_ALERT_2_C Short Inter D-H..H-D H9 .. H12 .. 2.12 Ang.
0 ALERT level A = In general: serious problem
0 ALERT level B = Potentially serious problem
3 ALERT level C = Check and explain
0 ALERT level G = General alerts; check
1 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
2 ALERT type 2 Indicator that the structure model may be wrong or deficient
0 ALERT type 3 Indicator that the structure quality may be low
0 ALERT type 4 Improvement, methodology, query or suggestion
Data collection: SMART (Bruker, 1999); cell refinement: SAINT-Plus (Bruker, 1999); data reduction: SAINT-Plus; program(s) used to solve structure: SHELXTL (Sheldrick, 2000); program(s) used to refine structure: SHELXTL; molecular graphics: ORTEP-3 (Farrugia, 1997); software used to prepare material for publication: SHELXTL.
sodium 3-ammonium-1-hydroxypropylidene-1,1-bisphosphonate monohydrate
top
Crystal data top
Na+·C3H10NO7P2−·H2O | Z = 2 |
Mr = 275.07 | F(000) = 284 |
Triclinic, P1 | Dx = 1.883 Mg m−3 |
Hall symbol: -P 1 | Mo Kα radiation, λ = 0.71073 Å |
a = 5.8699 (5) Å | Cell parameters from 3147 reflections |
b = 9.1235 (8) Å | θ = 3.1–30.7° |
c = 9.3113 (8) Å | µ = 0.52 mm−1 |
α = 86.746 (2)° | T = 120 K |
β = 77.125 (2)° | Lath like, colorless |
γ = 87.728 (2)° | 0.35 × 0.08 × 0.02 mm |
V = 485.15 (7) Å3 | |
Data collection top
Bruker SMART APEX diffractometer | 2811 independent reflections |
Radiation source: fine-focus sealed tube | 2543 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.027 |
ω scans, frame data integration | θmax = 30.8°, θmin = 2.2° |
Absorption correction: multi-scan SADABS (Sheldrick, 2002) | h = −8→8 |
Tmin = 0.8, Tmax = 1.0 | k = −13→13 |
6525 measured reflections | l = −13→13 |
Refinement top
Refinement on F2 | Primary atom site location: structure-invariant direct methods |
Least-squares matrix: full | Secondary atom site location: difference Fourier map |
R[F2 > 2σ(F2)] = 0.045 | Hydrogen site location: difference Fourier map |
wR(F2) = 0.111 | H atoms treated by a mixture of independent and constrained refinement |
S = 1.10 | w = 1/[σ2(Fo2) + (0.056P)2 + 0.4254P] where P = (Fo2 + 2Fc2)/3 |
2811 reflections | (Δ/σ)max < 0.001 |
160 parameters | Δρmax = 0.96 e Å−3 |
5 restraints | Δρmin = −0.44 e Å−3 |
Special details top
Experimental. Oxford Cryosystem liquid nitrogen cryostream cooler |
Geometry. All e.s.d.'s (except the e.s.d. in the dihedral angle between two l.s. planes)
are estimated using the full covariance matrix. The cell e.s.d.'s are taken
into account individually in the estimation of e.s.d.'s in distances, angles
and torsion angles; correlations between e.s.d.'s in cell parameters are only
used when they are defined by crystal symmetry. An approximate (isotropic)
treatment of cell e.s.d.'s is used for estimating e.s.d.'s involving l.s.
planes. |
Refinement. Refinement of F2 against ALL reflections. The weighted R-factor
wR and goodness of fit S are based on F2, conventional
R-factors R are based on F, with F set to zero for
negative F2. The threshold expression of F2 >
2σ(F2) is used only for calculating R-factors(gt) etc.
and is not relevant to the choice of reflections for refinement.
R-factors based on F2 are statistically about twice as large
as those based on F, and R- factors based on ALL data will be
even larger. |
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top | x | y | z | Uiso*/Ueq | |
Na | −0.29895 (14) | 0.39826 (9) | −0.11810 (9) | 0.00902 (18) | |
O8 | −0.1372 (3) | 0.30519 (18) | −0.52726 (18) | 0.0130 (3) | |
H11 | −0.255 (4) | 0.322 (3) | −0.457 (3) | 0.020* | |
H12 | −0.126 (5) | 0.376 (3) | −0.587 (3) | 0.020* | |
P1 | 0.14952 (9) | 0.25656 (5) | 0.04207 (5) | 0.00579 (13) | |
O1 | −0.0999 (2) | 0.33818 (16) | 0.07714 (16) | 0.0083 (3) | |
H10 | −0.095 (5) | 0.402 (3) | 0.135 (3) | 0.012* | |
O2 | 0.1462 (3) | 0.12529 (15) | 0.14890 (16) | 0.0090 (3) | |
O3 | 0.3404 (3) | 0.36108 (15) | 0.03975 (16) | 0.0085 (3) | |
P2 | 0.26402 (9) | 0.33484 (5) | −0.28981 (5) | 0.00640 (13) | |
O4 | 0.0906 (3) | 0.46301 (15) | −0.25636 (16) | 0.0084 (3) | |
O5 | 0.2384 (3) | 0.26740 (16) | −0.43723 (16) | 0.0093 (3) | |
H9 | 0.112 (4) | 0.288 (3) | −0.462 (3) | 0.014* | |
O6 | 0.5157 (3) | 0.36392 (16) | −0.30145 (16) | 0.0102 (3) | |
O7 | −0.0656 (3) | 0.15823 (15) | −0.15782 (17) | 0.0086 (3) | |
H8 | −0.084 (5) | 0.071 (2) | −0.161 (3) | 0.013* | |
C1 | 0.1666 (3) | 0.1903 (2) | −0.1451 (2) | 0.0063 (3) | |
C2 | 0.3327 (4) | 0.0552 (2) | −0.1592 (2) | 0.0085 (4) | |
H1 | 0.4813 | 0.0840 | −0.1394 | 0.010* | |
H2 | 0.2661 | −0.0186 | −0.0823 | 0.010* | |
C3 | 0.3840 (4) | −0.0168 (2) | −0.3071 (2) | 0.0091 (4) | |
H3 | 0.2395 | −0.0238 | −0.3421 | 0.011* | |
H4 | 0.4940 | 0.0420 | −0.3805 | 0.011* | |
N1 | 0.4874 (3) | −0.16689 (19) | −0.2859 (2) | 0.0097 (3) | |
H5 | 0.619 (5) | −0.167 (3) | −0.243 (3) | 0.015* | |
H6 | 0.382 (5) | −0.227 (3) | −0.227 (3) | 0.015* | |
H7 | 0.527 (5) | −0.206 (3) | −0.371 (3) | 0.015* | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
Na | 0.0085 (4) | 0.0084 (4) | 0.0108 (4) | −0.0018 (3) | −0.0030 (3) | −0.0011 (3) |
O8 | 0.0127 (7) | 0.0148 (7) | 0.0113 (7) | 0.0020 (6) | −0.0029 (6) | 0.0012 (6) |
P1 | 0.0066 (2) | 0.0042 (2) | 0.0068 (2) | −0.00070 (16) | −0.00188 (18) | −0.00056 (16) |
O1 | 0.0069 (6) | 0.0077 (6) | 0.0110 (7) | 0.0005 (5) | −0.0028 (5) | −0.0032 (5) |
O2 | 0.0129 (7) | 0.0060 (6) | 0.0086 (7) | −0.0012 (5) | −0.0030 (5) | 0.0002 (5) |
O3 | 0.0086 (7) | 0.0060 (6) | 0.0112 (7) | −0.0035 (5) | −0.0021 (5) | −0.0020 (5) |
P2 | 0.0075 (2) | 0.0051 (2) | 0.0068 (2) | −0.00044 (17) | −0.00178 (18) | −0.00077 (16) |
O4 | 0.0108 (7) | 0.0044 (6) | 0.0100 (7) | 0.0009 (5) | −0.0021 (5) | −0.0015 (5) |
O5 | 0.0100 (7) | 0.0109 (7) | 0.0078 (7) | 0.0017 (5) | −0.0035 (5) | −0.0028 (5) |
O6 | 0.0085 (7) | 0.0130 (7) | 0.0094 (7) | −0.0023 (5) | −0.0023 (5) | −0.0001 (5) |
O7 | 0.0077 (7) | 0.0055 (6) | 0.0139 (7) | −0.0016 (5) | −0.0045 (5) | −0.0017 (5) |
C1 | 0.0069 (8) | 0.0049 (8) | 0.0076 (8) | −0.0006 (6) | −0.0023 (7) | −0.0019 (6) |
C2 | 0.0097 (9) | 0.0077 (8) | 0.0081 (8) | 0.0010 (7) | −0.0023 (7) | −0.0012 (6) |
C3 | 0.0115 (9) | 0.0052 (8) | 0.0107 (9) | 0.0024 (7) | −0.0027 (7) | −0.0012 (6) |
N1 | 0.0131 (9) | 0.0054 (7) | 0.0109 (8) | 0.0014 (6) | −0.0031 (7) | −0.0015 (6) |
Geometric parameters (Å, º) top
Na—O6i | 2.2611 (17) | P2—O5 | 1.5751 (15) |
Na—O3i | 2.3174 (16) | P2—C1 | 1.843 (2) |
Na—O3ii | 2.3394 (16) | O5—H9 | 0.837 (17) |
Na—O1 | 2.3987 (17) | O7—C1 | 1.436 (2) |
Na—O4 | 2.4382 (17) | O7—H8 | 0.807 (17) |
Na—O7 | 2.5371 (17) | C1—C2 | 1.534 (3) |
O8—H11 | 0.852 (17) | C2—C3 | 1.523 (3) |
O8—H12 | 0.818 (17) | C2—H1 | 0.9800 |
P1—O3 | 1.4956 (15) | C2—H2 | 0.9800 |
P1—O2 | 1.5108 (14) | C3—N1 | 1.496 (2) |
P1—O1 | 1.5913 (15) | C3—H3 | 0.9800 |
P1—C1 | 1.858 (2) | C3—H4 | 0.9800 |
O1—H10 | 0.817 (17) | N1—H5 | 0.94 (3) |
P2—O6 | 1.4902 (15) | N1—H6 | 0.91 (3) |
P2—O4 | 1.5185 (15) | N1—H7 | 0.87 (3) |
| | | |
O6i—Na—O3i | 85.65 (6) | O5—P2—C1 | 104.85 (8) |
O6i—Na—O3ii | 113.04 (6) | P2—O5—H9 | 115 (2) |
O3i—Na—O3ii | 85.70 (6) | C1—O7—H8 | 112 (2) |
O6i—Na—O1 | 158.87 (6) | O7—C1—C2 | 113.34 (15) |
O3i—Na—O1 | 91.46 (6) | O7—C1—P2 | 104.80 (12) |
O3ii—Na—O1 | 87.54 (6) | C2—C1—P2 | 112.75 (13) |
O6i—Na—O4 | 101.74 (6) | O7—C1—P1 | 108.29 (13) |
O3i—Na—O4 | 171.20 (6) | C2—C1—P1 | 106.06 (13) |
O3ii—Na—O4 | 86.98 (6) | P2—C1—P1 | 111.64 (10) |
O1—Na—O4 | 83.34 (6) | C3—C2—C1 | 116.35 (16) |
O6i—Na—O7 | 93.08 (6) | C3—C2—H1 | 108 |
O3i—Na—O7 | 110.80 (6) | C1—C2—H1 | 108 |
O3ii—Na—O7 | 150.48 (6) | C3—C2—H2 | 108 |
O1—Na—O7 | 68.39 (5) | C1—C2—H2 | 108 |
O4—Na—O7 | 73.91 (5) | H1—C2—H2 | 107 |
H11—O8—H12 | 108 (3) | N1—C3—C2 | 108.03 (16) |
O3—P1—O2 | 114.45 (8) | N1—C3—H3 | 110 |
O3—P1—O1 | 111.03 (8) | C2—C3—H3 | 110 |
O2—P1—O1 | 108.83 (8) | N1—C3—H4 | 110 |
O3—P1—C1 | 110.64 (8) | C2—C3—H4 | 110 |
O2—P1—C1 | 108.74 (8) | H3—C3—H4 | 108 |
O1—P1—C1 | 102.45 (8) | C3—N1—H5 | 113.5 (18) |
P1—O1—H10 | 108 (2) | C3—N1—H6 | 111.6 (19) |
O6—P2—O4 | 117.49 (9) | H5—N1—H6 | 107 (2) |
O6—P2—O5 | 108.37 (9) | C3—N1—H7 | 108.3 (19) |
O4—P2—O5 | 108.96 (8) | H5—N1—H7 | 109 (3) |
O6—P2—C1 | 109.99 (9) | H6—N1—H7 | 107 (3) |
O4—P2—C1 | 106.46 (8) | | |
Symmetry codes: (i) x−1, y, z; (ii) −x, −y+1, −z. |
Hydrogen-bond geometry (Å, º) top
D—H···A | D—H | H···A | D···A | D—H···A |
N1—H5···O2iii | 0.94 (3) | 1.85 (3) | 2.782 (2) | 167 (3) |
N1—H6···O1iv | 0.91 (3) | 2.16 (3) | 3.060 (2) | 171 (3) |
N1—H7···O5v | 0.87 (3) | 2.09 (3) | 2.895 (2) | 155 (3) |
O7—H8···O2iv | 0.81 (2) | 1.84 (2) | 2.641 (2) | 174 (3) |
O5—H9···O8 | 0.84 (2) | 1.70 (2) | 2.532 (2) | 171 (3) |
O1—H10···O4ii | 0.82 (2) | 1.73 (2) | 2.544 (2) | 179 (3) |
O8—H11···O6i | 0.85 (2) | 1.79 (2) | 2.644 (2) | 175 (3) |
O8—H12···O4vi | 0.82 (2) | 2.00 (2) | 2.815 (2) | 176 (3) |
Symmetry codes: (i) x−1, y, z; (ii) −x, −y+1, −z; (iii) −x+1, −y, −z; (iv) −x, −y, −z; (v) −x+1, −y, −z−1; (vi) −x, −y+1, −z−1. |