Bis(1,10-phenanthroline-κ²N,N′)platinum(II) bis­(3-carb­oxy­benzene­sulfonate) dihydrate

The title complex, [Pt(C₁₂H₈N₂)₂](C₇H₅O₅S)₂·2H₂O, consists of a complex cation [Pt(1,10-phen)₂]²⁺ (1,10-phen = 1,10-phenanthroline), two 3-sulfobenzoate anions and two lattice water mol­ecules. In the crystal, anions and water mol­ecules form hydrogen-bonded centrosymmetric dimers. In addition, π–π inter­actions are observed between 1,10-phenanthroline ligands and 3-sulfobenzoate anions.

Key indicators

• Single-crystal X-ray study
• T = 295 K
• Mean [sigma](C-C) = 0.014 Å
• R factor = 0.050
• wR factor = 0.122
• Data-to-parameter ratio = 11.6

checkCIF/PLATON results

No syntax errors found



Alert level B
PLAT213_ALERT_2_B Atom O3              has ADP max/min Ratio .....        4.2 prolat

Author Response: Although the sulfonate group seems to be disordered due to the thermal parameters of oxygen atoms, disorder has not been resolved because the refinement then did not converge.

Alert level C
PLAT234_ALERT_4_C Large Hirshfeld Difference O1     --  C13     ..       0.18 Ang.
PLAT242_ALERT_2_C Low    'MainMol' Ueq as Compared to Neighbors of         S1 Check
PLAT342_ALERT_3_C Low Bond Precision on  C-C Bonds ...............    0.01416 Ang.
PLAT906_ALERT_3_C Large K value in the Analysis of Variance ......     19.890 Check
PLAT906_ALERT_3_C Large K value in the Analysis of Variance ......      4.042 Check
PLAT910_ALERT_3_C Missing # of FCF Reflection(s) Below Th(Min) ...          6 Report
PLAT911_ALERT_3_C Missing # FCF Refl Between THmin & STh/L=  0.596          3 Report
PLAT975_ALERT_2_C Check Calcd Residual Density  0.97A From      O2       0.49 eA-3
PLAT976_ALERT_2_C Check Calcd Residual Density  0.94A From      O4      -0.41 eA-3
PLAT978_ALERT_2_C Number C-C Bonds with Positive Residual Density           0 Note

Alert level G
PLAT002_ALERT_2_G Number of Distance or Angle Restraints on AtSite          4 Note
PLAT005_ALERT_5_G No Embedded Refinement Details found  in the CIF     Please Do !
PLAT007_ALERT_5_G Number of Unrefined Donor-H Atoms ..............          1 Report
PLAT008_ALERT_5_G No _iucr_refine_reflections_details   in the CIF     Please Do !
PLAT484_ALERT_4_G Round D-H..A Angle Rep for O2     ..  O1W     to        177 Degree
PLAT790_ALERT_4_G Centre of Gravity not Within Unit Cell: Resd.  #          2 Note
              C7 H5 O5 S
PLAT860_ALERT_3_G Number of Least-Squares Restraints .............          5 Note
PLAT899_ALERT_4_G SHELXL97   is Deprecated and Succeeded by SHELXL       2014 Note
PLAT909_ALERT_3_G Percentage of Observed Data at Theta(Max) Still          57 %

   0 ALERT level A = Most likely a serious problem - resolve or explain
   1 ALERT level B = A potentially serious problem, consider carefully
  10 ALERT level C = Check. Ensure it is not caused by an omission or oversight
   9 ALERT level G = General information/check it is not something unexpected

   0 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
   6 ALERT type 2 Indicator that the structure model may be wrong or deficient
   7 ALERT type 3 Indicator that the structure quality may be low
   4 ALERT type 4 Improvement, methodology, query or suggestion
   3 ALERT type 5 Informative message, check

---

Computing details

Data collection: CrysAlis PRO (Oxford Diffraction, 2009); cell refinement: CrysAlis PRO (Oxford Diffraction, 2009); data reduction: CrysAlis PRO (Oxford Diffraction, 2009); molecular graphics: ORTEP-3 for Windows (Farrugia, 2012); software used to prepare material for publication: WinGX (Farrugia, 2012).

Bis(1,10-phenanthroline-κ²N,N')platinum(II) bis(3-carboxybenzenesulfonate) dihydrate

Crystal data

[Pt(C12H8N2)2](C7H5O5S)2·2H2O	F(000) = 984
Mr = 993.87	Dx = 1.883 Mg m^−3
Monoclinic, P21/n	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2yn	Cell parameters from 2156 reflections
a = 6.9957 (7) Å	θ = 2.9–29.2°
b = 12.0819 (10) Å	µ = 4.20 mm^−1
c = 20.904 (2) Å	T = 295 K
β = 97.296 (10)°	Needle, brown
V = 1752.5 (3) Å^3	0.40 × 0.15 × 0.13 mm
Z = 2

Data collection

Oxford Diffraction Xcalibur Atlas Gemini ultra diffractometer	3087 independent reflections
Radiation source: fine-focus sealed tube	2202 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.047
ω scans	θmax = 25.1°, θmin = 3.4°
Absorption correction: multi-scan (CrysAlis PRO; Oxford Diffraction, 2009)	h = −8→7
Tmin = 0.285, Tmax = 0.611	k = −14→11
7677 measured reflections	l = −24→22

Refinement

Refinement on F^2	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F^2 > 2σ(F^2)] = 0.050	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.122	H atoms treated by a mixture of independent and constrained refinement
S = 1.16	w = 1/[σ^2(Fo^2) + (0.0463P)^2 + 1.9422P] where P = (Fo^2 + 2Fc^2)/3
3087 reflections	(Δ/σ)max < 0.001
265 parameters	Δρmax = 1.35 e Å^−3
5 restraints	Δρmin = −0.76 e Å^−3

Special details

Experimental. Absorption correction: CrysAlisPro, Oxford Diffraction Ltd., Version 1.171.33.53 (release 17-11-2009 CrysAlis171 .NET) (compiled Nov 17 2009,16:58:22) Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm.

Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds 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 > 2sigma(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 (Ų)

	x	y	z	Uiso*/Ueq
O1W	0.4465 (17)	0.3570 (11)	0.1629 (4)	0.135 (5)
H1A	0.48 (3)	0.413 (4)	0.186 (3)	0.160*
H1B	0.44 (3)	0.302 (5)	0.189 (2)	0.160*
Pt1	0.0000	0.0000	0.0000	0.03467 (18)
S1	0.2546 (4)	0.3824 (3)	−0.22026 (14)	0.0649 (8)
N1	0.1230 (9)	−0.0662 (5)	0.0841 (3)	0.0354 (16)
C12	0.1129 (11)	−0.2246 (7)	0.0181 (5)	0.040 (2)
C11	0.1365 (11)	−0.1803 (7)	0.0815 (4)	0.037 (2)
C14	0.3660 (11)	0.2165 (7)	−0.0524 (4)	0.0346 (19)
C19	0.3717 (12)	0.1080 (7)	−0.0727 (4)	0.042 (2)
H19	0.4000	0.0515	−0.0427	0.050*
N2	0.0730 (9)	−0.1517 (5)	−0.0315 (3)	0.0356 (16)
C15	0.3292 (11)	0.3015 (7)	−0.0961 (4)	0.040 (2)
H15	0.3283	0.3746	−0.0822	0.047*
C16	0.2934 (12)	0.2762 (8)	−0.1612 (4)	0.042 (2)
C8	0.1435 (14)	−0.3731 (8)	−0.0563 (6)	0.062 (3)
H8	0.1646	−0.4472	−0.0652	0.074*
O2	0.3736 (11)	0.3364 (6)	0.0359 (3)	0.070 (2)
H2A	0.3916	0.3416	0.0753	0.106*
C18	0.3351 (13)	0.0836 (8)	−0.1375 (5)	0.047 (2)
H18	0.3365	0.0106	−0.1515	0.057*
C4	0.1922 (12)	−0.2446 (8)	0.1343 (5)	0.048 (2)
O1	0.4453 (11)	0.1592 (6)	0.0573 (3)	0.072 (2)
O5	0.4059 (10)	0.3743 (6)	−0.2592 (3)	0.071 (2)
C7	0.1426 (12)	−0.3370 (7)	0.0087 (5)	0.051 (3)
C5	0.2090 (15)	−0.3632 (9)	0.1251 (6)	0.065 (3)
H5	0.2319	−0.4104	0.1604	0.078*
C17	0.2968 (13)	0.1676 (9)	−0.1812 (5)	0.051 (2)
H17	0.2728	0.1512	−0.2250	0.061*
C6	0.1908 (14)	−0.4040 (9)	0.0645 (6)	0.063 (3)
H6	0.2107	−0.4793	0.0589	0.075*
C2	0.2373 (14)	−0.0813 (10)	0.1967 (5)	0.060 (3)
H2	0.2756	−0.0454	0.2356	0.071*
C13	0.3961 (13)	0.2350 (9)	0.0194 (5)	0.051 (2)
C9	0.1130 (14)	−0.2979 (9)	−0.1053 (5)	0.058 (3)
H9	0.1125	−0.3205	−0.1479	0.070*
C10	0.0829 (13)	−0.1876 (8)	−0.0911 (5)	0.050 (2)
H10	0.0690	−0.1366	−0.1247	0.060*
C1	0.1804 (14)	−0.0196 (8)	0.1412 (5)	0.052 (3)
H1	0.1826	0.0572	0.1440	0.062*
C3	0.2370 (13)	−0.1932 (10)	0.1941 (5)	0.060 (3)
H3	0.2659	−0.2350	0.2314	0.071*
O3	0.249 (2)	0.4796 (7)	−0.1881 (5)	0.158 (6)
O4	0.0693 (13)	0.3532 (9)	−0.2588 (5)	0.132 (4)

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
O1W	0.098 (7)	0.268 (15)	0.039 (5)	0.036 (10)	0.005 (5)	−0.033 (6)
Pt1	0.0381 (3)	0.0305 (3)	0.0373 (3)	0.0038 (3)	0.01218 (19)	0.0002 (2)
S1	0.0707 (18)	0.0720 (19)	0.0559 (17)	0.0306 (16)	0.0230 (14)	0.0305 (15)
N1	0.031 (4)	0.035 (4)	0.043 (4)	0.004 (3)	0.013 (3)	0.003 (3)
C12	0.021 (4)	0.040 (5)	0.063 (6)	0.006 (4)	0.014 (4)	0.001 (4)
C11	0.025 (4)	0.038 (5)	0.051 (6)	0.004 (4)	0.017 (4)	0.008 (4)
C14	0.023 (4)	0.045 (5)	0.036 (5)	−0.004 (4)	0.005 (4)	−0.001 (4)
C19	0.040 (5)	0.046 (5)	0.040 (5)	0.000 (4)	0.006 (4)	0.008 (4)
N2	0.033 (4)	0.034 (4)	0.041 (4)	0.008 (3)	0.007 (3)	0.000 (3)
C15	0.038 (5)	0.037 (5)	0.046 (6)	0.011 (4)	0.014 (4)	0.000 (4)
C16	0.041 (5)	0.051 (6)	0.038 (5)	0.006 (4)	0.014 (4)	0.013 (4)
C8	0.047 (6)	0.037 (6)	0.105 (10)	0.001 (5)	0.020 (6)	−0.027 (6)
O2	0.089 (5)	0.082 (6)	0.037 (4)	0.015 (5)	0.001 (4)	−0.015 (4)
C18	0.052 (6)	0.040 (5)	0.051 (6)	−0.012 (5)	0.013 (5)	−0.001 (4)
C4	0.029 (5)	0.062 (6)	0.057 (7)	0.004 (5)	0.013 (4)	0.019 (5)
O1	0.094 (6)	0.078 (5)	0.042 (4)	0.001 (5)	−0.006 (4)	0.020 (4)
O5	0.071 (5)	0.090 (5)	0.057 (5)	0.016 (4)	0.029 (4)	0.028 (4)
C7	0.033 (5)	0.031 (5)	0.089 (8)	−0.002 (4)	0.004 (5)	0.001 (5)
C5	0.059 (7)	0.053 (7)	0.084 (9)	0.007 (6)	0.016 (6)	0.029 (6)
C17	0.046 (5)	0.070 (7)	0.035 (5)	−0.002 (5)	0.004 (4)	−0.014 (5)
C6	0.052 (6)	0.037 (6)	0.102 (10)	0.003 (5)	0.020 (6)	0.009 (6)
C2	0.058 (6)	0.085 (8)	0.036 (6)	0.021 (6)	0.008 (5)	0.001 (5)
C13	0.034 (5)	0.063 (7)	0.056 (7)	−0.009 (5)	0.011 (5)	−0.014 (6)
C9	0.052 (6)	0.054 (7)	0.071 (8)	0.000 (5)	0.014 (5)	−0.029 (6)
C10	0.056 (6)	0.056 (6)	0.041 (6)	0.003 (5)	0.018 (5)	−0.007 (5)
C1	0.054 (6)	0.061 (7)	0.041 (6)	0.014 (5)	0.011 (5)	−0.010 (5)
C3	0.043 (5)	0.091 (9)	0.046 (7)	0.011 (6)	0.008 (5)	0.031 (6)
O3	0.328 (19)	0.060 (6)	0.110 (8)	0.082 (8)	0.120 (10)	0.058 (6)
O4	0.078 (6)	0.169 (11)	0.142 (9)	0.017 (7)	−0.013 (6)	0.098 (8)

Geometric parameters (Å, º)

O1W—H1A	0.845 (19)	C16—C17	1.378 (13)
O1W—H1B	0.87 (2)	C8—C9	1.365 (15)
Pt1—N1	2.022 (7)	C8—C7	1.428 (14)
Pt1—N1^i	2.022 (7)	C8—H8	0.9300
Pt1—N2^i	2.034 (6)	O2—C13	1.289 (11)
Pt1—N2	2.034 (6)	O2—H2A	0.8200
S1—O3	1.357 (10)	C18—C17	1.368 (13)
S1—O5	1.418 (7)	C18—H18	0.9300
S1—O4	1.479 (10)	C4—C3	1.396 (14)
S1—C16	1.777 (9)	C4—C5	1.452 (14)
N1—C1	1.333 (11)	O1—C13	1.231 (12)
N1—C11	1.384 (10)	C7—C6	1.424 (14)
C12—N2	1.362 (11)	C5—C6	1.349 (15)
C12—C7	1.392 (12)	C5—H5	0.9300
C12—C11	1.419 (12)	C17—H17	0.9300
C11—C4	1.365 (12)	C6—H6	0.9300
C14—C15	1.377 (11)	C2—C3	1.353 (15)
C14—C19	1.381 (12)	C2—C1	1.394 (13)
C14—C13	1.505 (12)	C2—H2	0.9300
C19—C18	1.380 (12)	C9—C10	1.388 (13)
C19—H19	0.9300	C9—H9	0.9300
N2—C10	1.331 (11)	C10—H10	0.9300
C15—C16	1.386 (12)	C1—H1	0.9300
C15—H15	0.9300	C3—H3	0.9300
H1A—O1W—H1B	107 (3)	C7—C8—H8	120.2
N1—Pt1—N1^i	180.0 (4)	C13—O2—H2A	109.5
N1—Pt1—N2^i	99.9 (3)	C17—C18—C19	119.6 (9)
N1^i—Pt1—N2^i	80.1 (3)	C17—C18—H18	120.2
N1—Pt1—N2	80.1 (3)	C19—C18—H18	120.2
N1^i—Pt1—N2	99.9 (3)	C11—C4—C3	118.6 (10)
N2^i—Pt1—N2	180.0 (5)	C11—C4—C5	118.3 (10)
O3—S1—O5	114.6 (7)	C3—C4—C5	123.1 (9)
O3—S1—O4	113.4 (8)	C12—C7—C6	117.6 (10)
O5—S1—O4	109.7 (6)	C12—C7—C8	116.7 (9)
O3—S1—C16	107.0 (5)	C6—C7—C8	125.2 (10)
O5—S1—C16	106.8 (4)	C6—C5—C4	119.0 (10)
O4—S1—C16	104.6 (5)	C6—C5—H5	120.5
C1—N1—C11	116.2 (8)	C4—C5—H5	120.5
C1—N1—Pt1	131.1 (6)	C18—C17—C16	120.8 (9)
C11—N1—Pt1	112.5 (6)	C18—C17—H17	119.6
N2—C12—C7	123.0 (9)	C16—C17—H17	119.6
N2—C12—C11	117.1 (8)	C5—C6—C7	123.0 (10)
C7—C12—C11	119.8 (9)	C5—C6—H6	118.5
C4—C11—N1	123.3 (9)	C7—C6—H6	118.5
C4—C11—C12	121.8 (9)	C3—C2—C1	120.1 (10)
N1—C11—C12	114.3 (8)	C3—C2—H2	119.9
C15—C14—C19	121.0 (8)	C1—C2—H2	119.9
C15—C14—C13	122.8 (8)	O1—C13—O2	124.7 (10)
C19—C14—C13	116.2 (8)	O1—C13—C14	121.6 (9)
C18—C19—C14	119.7 (8)	O2—C13—C14	113.7 (9)
C18—C19—H19	120.2	C8—C9—C10	119.5 (10)
C14—C19—H19	120.2	C8—C9—H9	120.3
C10—N2—C12	118.2 (8)	C10—C9—H9	120.3
C10—N2—Pt1	129.9 (6)	N2—C10—C9	122.7 (9)
C12—N2—Pt1	111.9 (6)	N2—C10—H10	118.6
C14—C15—C16	118.8 (8)	C9—C10—H10	118.6
C14—C15—H15	120.6	N1—C1—C2	122.7 (10)
C16—C15—H15	120.6	N1—C1—H1	118.6
C17—C16—C15	120.0 (8)	C2—C1—H1	118.6
C17—C16—S1	118.9 (7)	C2—C3—C4	118.7 (9)
C15—C16—S1	121.0 (7)	C2—C3—H3	120.6
C9—C8—C7	119.5 (9)	C4—C3—H3	120.6
C9—C8—H8	120.2
N2^i—Pt1—N1—C1	−13.2 (8)	N1—C11—C4—C3	0.4 (13)
N2—Pt1—N1—C1	166.8 (8)	C12—C11—C4—C3	171.7 (8)
N2^i—Pt1—N1—C11	162.1 (5)	N1—C11—C4—C5	−177.4 (8)
N2—Pt1—N1—C11	−17.9 (5)	C12—C11—C4—C5	−6.1 (13)
C1—N1—C11—C4	4.4 (12)	N2—C12—C7—C6	177.6 (8)
Pt1—N1—C11—C4	−171.7 (6)	C11—C12—C7—C6	1.8 (12)
C1—N1—C11—C12	−167.5 (7)	N2—C12—C7—C8	4.4 (13)
Pt1—N1—C11—C12	16.4 (8)	C11—C12—C7—C8	−171.3 (8)
N2—C12—C11—C4	−174.5 (7)	C9—C8—C7—C12	−0.9 (14)
C7—C12—C11—C4	1.5 (12)	C9—C8—C7—C6	−173.5 (9)
N2—C12—C11—N1	−2.5 (11)	C11—C4—C5—C6	7.5 (14)
C7—C12—C11—N1	173.5 (7)	C3—C4—C5—C6	−170.2 (9)
C15—C14—C19—C18	−1.7 (12)	C19—C18—C17—C16	−0.3 (14)
C13—C14—C19—C18	176.6 (8)	C15—C16—C17—C18	0.1 (14)
C7—C12—N2—C10	−7.2 (12)	S1—C16—C17—C18	176.9 (7)
C11—C12—N2—C10	168.7 (7)	C4—C5—C6—C7	−4.4 (16)
C7—C12—N2—Pt1	171.6 (6)	C12—C7—C6—C5	−0.2 (15)
C11—C12—N2—Pt1	−12.5 (9)	C8—C7—C6—C5	172.3 (10)
N1—Pt1—N2—C10	−165.0 (8)	C15—C14—C13—O1	−173.6 (9)
N1^i—Pt1—N2—C10	15.0 (8)	C19—C14—C13—O1	8.2 (12)
N1—Pt1—N2—C12	16.4 (5)	C15—C14—C13—O2	3.7 (12)
N1^i—Pt1—N2—C12	−163.6 (5)	C19—C14—C13—O2	−174.5 (8)
C19—C14—C15—C16	1.4 (12)	C7—C8—C9—C10	0.4 (15)
C13—C14—C15—C16	−176.7 (7)	C12—N2—C10—C9	6.6 (13)
C14—C15—C16—C17	−0.6 (13)	Pt1—N2—C10—C9	−172.0 (7)
C14—C15—C16—S1	−177.4 (6)	C8—C9—C10—N2	−3.3 (15)
O3—S1—C16—C17	177.2 (10)	C11—N1—C1—C2	−4.8 (13)
O5—S1—C16—C17	−59.7 (8)	Pt1—N1—C1—C2	170.4 (7)
O4—S1—C16—C17	56.6 (9)	C3—C2—C1—N1	0.4 (15)
O3—S1—C16—C15	−6.0 (11)	C1—C2—C3—C4	4.6 (15)
O5—S1—C16—C15	117.2 (8)	C11—C4—C3—C2	−4.9 (14)
O4—S1—C16—C15	−126.6 (8)	C5—C4—C3—C2	172.8 (9)
C14—C19—C18—C17	1.1 (13)

Symmetry code: (i) −x, −y, −z.

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
O2—H2A···O1W	0.82	1.83	2.650 (10)	177
O1W—H1A···O3^ii	0.85 (2)	2.32 (14)	2.90 (2)	126 (14)
C6—H6···O2^iii	0.93	2.57	3.468 (13)	161
C10—H1···O5^iv	0.93	2.46	3.228 (12)	140

Symmetry codes: (ii) −x+1, −y+1, −z; (iii) x, y−1, z; (iv) −x+1/2, y−1/2, −z−1/2.