Bis[4-amino-N-(pyrimidin-2-yl)benzene­sulfonamidato](1,10-phenanthroline)nickel(II)

Hu, X.-F.; Bing, Y.; Li, X.; Kong, Z.-P.

doi:10.1107/S1600536812008185

metal-organic compounds

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ISSN: 2056-9890

Volume 68| Part 3| March 2012| Pages m348-m349

doi:10.1107/S1600536812008185

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Bis[4-amino-N-(pyrimidin-2-yl)benzenesulfonamidato](1,10-phenanthroline)nickel(II)

Xiu-Feng Hu,^a Yue Bing,^a Xing Li ^a ^* and Zu-Ping Kong ^a

^aFaculty of Materials Science and Chemical Engineering, Ningbo University, Ningbo, Zhejiang 315211, People's Republic of China
^*Correspondence e-mail: lix905@126.com

(Received 13 January 2012; accepted 23 February 2012; online 29 February 2012)

In the mononuclear title compound, [Ni(C₁₀H₉N₄O₂S)₂(C₁₂H₈N₂)], the Ni^II atom has a distorted octahedral coordination geometry comprising four N atoms from two 4-amino-N-(pyrimidin-2-yl)benzenesulfonamidate ligands and two N atoms from a 1,10-phenanthroline ligand. In the crystal, molecules are connected into a three-dimensional supramolecular network via N—H⋯O hydrogen bonds and weak C—H⋯O and C—H⋯N contacts.

Related literature

For related literature regarding the properties of 4-amino-N-(pyrimidin-2-yl)benzenesulfonamidate ligands, see: Ellena et al. (2007 ); Garcia-Raso et al. (1997 ). For related literature regarding crystal engineering studies of 4-amino-N-(pyrimidin-2-yl) benzenesulfonamidate ligands, see: Garcia-Raso et al. (2000 ); Golzar Hossain et al. (2007 ); Gutierrez et al. (2001 ).

Experimental

Crystal data

[Ni(C₁₀H₉N₄O₂S)₂(C₁₂H₈N₂)]
M_r = 737.46
Orthorhombic, P c a 2₁
a = 11.015 (2) Å
b = 17.995 (3) Å
c = 16.128 (3) Å
V = 3196.9 (10) Å³
Z = 4
Mo Kα radiation
μ = 0.79 mm⁻¹
T = 293 K
0.34 × 0.26 × 0.18 mm

Data collection

Bruker SMART APEXII CCD area-detector diffractometer
Absorption correction: multi-scan (ABSCOR; Higashi, 1995 ) T_min = 0.774, T_max = 0.870
27217 measured reflections
7075 independent reflections
5020 reflections with I > 2σ(I)
R_int = 0.058

Refinement

R[F² > 2σ(F²)] = 0.044
wR(F²) = 0.110
S = 1.02
7075 reflections
431 parameters
2 restraints
H-atom parameters constrained
Δρ_max = 0.51 e Å⁻³
Δρ_min = −0.35 e Å⁻³
Absolute structure: Flack (1983 ), 3236 Friedel pairs
Flack parameter: 0.236 (16)

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1A⋯O1ⁱ	0.86	2.46	3.162 (6)	140
N1—H1B⋯O2ⁱⁱ	0.86	2.23	3.056 (6)	162
N5—H5A⋯O3ⁱⁱⁱ	0.86	2.52	3.285 (6)	148
N5—H5B⋯O4^iv	0.86	2.20	3.016 (6)	158
C5—H5C⋯O2^v	0.93	2.56	3.377 (5)	147
C12—H12A⋯N8ⁱⁱⁱ	0.93	2.56	3.470 (6)	166
Symmetry codes: (i) $[-x+1, -y, z+{\script{1\over 2}}]$ ; (ii) $[-x+{\script{1\over 2}}, y, z+{\script{1\over 2}}]$ ; (iii) $[-x-{\script{1\over 2}}, y, z+{\script{1\over 2}}]$ ; (iv) $[-x, -y+1, z+{\script{1\over 2}}]$ ; (v) $[x+{\script{1\over 2}}, -y, z]$ .

Data collection: SMART (Bruker, 2001 ); cell refinement: SAINT (Bruker, 2001); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXTL.

Supporting information

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536812008185/ez2279sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536812008185/ez2279Isup2.hkl

checkCIF report

Comment top

4-amino-N-(pyrimidin-2-yl)benzenesulfonamidato ligands have strong metal-binding properties as well as antibacterial functions (Ellena et al., 2007; Garcia-Raso et al., 1997). Crystal engineering studies of metal 4-amino-N-(pyrimidin-2-yl)benzenesulfonamidato complexes are less well developed (Garcia-Raso et al., 2000; Golzar et al., 2007; Gutierrez et al. 2001), and adding 1,10-phenanthroline as secondary ligand with 4-amino-N-(pyrimidin-2-yl)benzenesulfonamide to synthesize novel complex has not been reported yet, as far as we know. Here, we report the crystal structure of the title nickel complex with 1,10-phenanthroline and 4-amino-N-(pyrimidin-2-yl)benzenesulfonamide, (I).

Complex (I) is a mononuclear structure, in which the Ni^II atom has a distorted octahedral coordination geometry comprising four N atoms from two 4-amino-N-(pyrimidin-2-yl)benzenesulfonamidato ligands, two N atoms from a 1,10-phenanthroline ligand. Ni—N distances range from 2.064 to 2.205 Å (Figure 1). In the crystal, the molecules are connected into a three-dimensional supramolecular network via N—H···O hydrogen bonds and weak C—H···O and C—H···N contacts. (Figure 2).

Related literature top

For related literature regarding the properties of 4-amino-N-(pyrimidin-2-yl)benzenesulfonamidate ligands, see: Ellena et al. (2007); Garcia-Raso et al. (1997). For related literature regarding crystal engineering studies of 4-amino-N-(pyrimidin-2-yl) benzenesulfonamidate ligands, see: Garcia-Raso et al. (2000); Golzar et al. (2007); Gutierrez et al. (2001).

Experimental top

A mixture containing 0.005 mmol of 4-amino-N-(pyrimidin-2-yl)benzenesulfonamide, 0.005 mmol of Ni(OAc)₂, 0.005 mmol of 1,10-phenanthroline and 0.005 mmol of KOH was placed in a small vial containing H₂O (1.0 ml). The vial was sealed, heated at 373 K for 2 days, and allowed to cool to room temperature. Green crystals suitable for X-ray diffraction were collected and dried in air (yield, 31%).

Computing details top

Data collection: SMART (Bruker, 2001); cell refinement: SAINT (Bruker, 2001); data reduction: SAINT (Bruker, 2001); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXTL (Sheldrick, 2008).

Figures top

	Fig. 1. The molecular structure of (I) showing displacement ellipsoids at the 30% probability level.
	Fig. 2. Unit-cell contents for (I) viewed in projection down the a axis.

Bis[4-amino-N-(pyrimidin-2-yl)benzenesulfonamidato](1,10- phenanthroline)nickel(II) top

Crystal data top

[Ni(C₁₀H₉N₄O₂S)₂(C₁₂H₈N₂)]	F(000) = 1520
M_r = 737.46	D_x = 1.532 Mg m⁻³
Orthorhombic, Pca2₁	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2c -2ac	Cell parameters from 4514 reflections
a = 11.015 (2) Å	θ = 2.2–23.4°
b = 17.995 (3) Å	µ = 0.79 mm⁻¹
c = 16.128 (3) Å	T = 293 K
V = 3196.9 (10) Å³	Block, green
Z = 4	0.34 × 0.26 × 0.18 mm

Data collection top

Bruker SMART APEXII CCD area-detector diffractometer	7075 independent reflections
Radiation source: fine-focus sealed tube	5020 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.058
phi and ω scans	θ_max = 27.6°, θ_min = 2.2°
Absorption correction: multi-scan (ABSCOR; Higashi, 1995)	h = −14→14
T_min = 0.774, T_max = 0.870	k = −23→22
27217 measured reflections	l = −18→20

Refinement top

Refinement on F²	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F² > 2σ(F²)] = 0.044	H-atom parameters constrained
wR(F²) = 0.110	w = 1/[σ²(F_o²) + (0.0454P)² + 0.7787P] where P = (F_o² + 2F_c²)/3
S = 1.02	(Δ/σ)_max = 0.001
7075 reflections	Δρ_max = 0.51 e Å⁻³
431 parameters	Δρ_min = −0.35 e Å⁻³
2 restraints	Absolute structure: Flack (1983), 3236 Friedel pairs
Primary atom site location: structure-invariant direct methods	Absolute structure parameter: 0.236 (16)

Crystal data top

[Ni(C₁₀H₉N₄O₂S)₂(C₁₂H₈N₂)]	V = 3196.9 (10) Å³
M_r = 737.46	Z = 4
Orthorhombic, Pca2₁	Mo Kα radiation
a = 11.015 (2) Å	µ = 0.79 mm⁻¹
b = 17.995 (3) Å	T = 293 K
c = 16.128 (3) Å	0.34 × 0.26 × 0.18 mm

Data collection top

Bruker SMART APEXII CCD area-detector diffractometer	7075 independent reflections
Absorption correction: multi-scan (ABSCOR; Higashi, 1995)	5020 reflections with I > 2σ(I)
T_min = 0.774, T_max = 0.870	R_int = 0.058
27217 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.044	H-atom parameters constrained
wR(F²) = 0.110	Δρ_max = 0.51 e Å⁻³
S = 1.02	Δρ_min = −0.35 e Å⁻³
7075 reflections	Absolute structure: Flack (1983), 3236 Friedel pairs
431 parameters	Absolute structure parameter: 0.236 (16)
2 restraints

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. 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

	x	y	z	U_iso*/U_eq
Ni1	0.08935 (4)	0.25754 (2)	0.18766 (4)	0.04064 (12)
S1	0.26208 (7)	0.09491 (5)	0.18621 (8)	0.0421 (2)
S2	−0.12704 (9)	0.40536 (6)	0.14560 (7)	0.0451 (3)
O1	0.3501 (3)	0.07865 (16)	0.12315 (19)	0.0571 (8)
O2	0.1443 (2)	0.06087 (14)	0.1758 (2)	0.0553 (8)
O3	−0.2414 (2)	0.3700 (2)	0.1294 (2)	0.0745 (10)
O4	−0.1087 (3)	0.47423 (18)	0.1020 (2)	0.0692 (9)
N1	0.4429 (4)	−0.0080 (3)	0.5131 (3)	0.0859 (14)
H1B	0.4044	0.0048	0.5571	0.103*
H1A	0.5071	−0.0351	0.5168	0.103*
N2	0.2338 (2)	0.18145 (15)	0.1963 (3)	0.0420 (7)
N3	0.2674 (3)	0.30325 (16)	0.1940 (3)	0.0466 (7)
N4	0.4420 (3)	0.22257 (17)	0.1955 (3)	0.0468 (7)
N5	−0.1094 (5)	0.4790 (3)	0.5019 (3)	0.106 (2)
H5A	−0.1683	0.4659	0.5337	0.127*
H5B	−0.0489	0.5033	0.5219	0.127*
N6	−0.0154 (3)	0.34928 (16)	0.13242 (19)	0.0408 (7)
N7	0.0896 (3)	0.2665 (2)	0.0604 (2)	0.0460 (9)
N8	−0.0354 (3)	0.3499 (2)	−0.0161 (2)	0.0583 (10)
N9	−0.0642 (3)	0.19039 (18)	0.1896 (4)	0.0570 (8)
N10	0.0438 (5)	0.2643 (2)	0.3117 (3)	0.0667 (13)
C1	0.4020 (4)	0.0146 (3)	0.4366 (3)	0.0551 (11)
C2	0.2985 (4)	0.0583 (2)	0.4303 (3)	0.0533 (10)
H2A	0.2549	0.0705	0.4778	0.064*
C3	0.2601 (4)	0.0837 (2)	0.3543 (3)	0.0488 (10)
H3A	0.1919	0.1141	0.3515	0.059*
C4	0.3206 (3)	0.0651 (2)	0.2817 (3)	0.0395 (9)
C5	0.4211 (4)	0.0207 (2)	0.2871 (3)	0.0534 (11)
H5C	0.4623	0.0072	0.2390	0.064*
C6	0.4622 (4)	−0.0042 (3)	0.3629 (3)	0.0661 (13)
H6A	0.5310	−0.0340	0.3652	0.079*
C7	0.3218 (3)	0.23493 (18)	0.1954 (3)	0.0394 (8)
C8	0.3396 (4)	0.3626 (2)	0.1879 (4)	0.0585 (10)
H8A	0.3056	0.4099	0.1855	0.070*
C9	0.4641 (4)	0.3546 (2)	0.1849 (4)	0.0581 (10)
H9A	0.5152	0.3954	0.1791	0.070*
C10	0.5090 (3)	0.2838 (2)	0.1909 (3)	0.0522 (9)
H10A	0.5929	0.2782	0.1919	0.063*
C11	−0.1119 (4)	0.4612 (3)	0.4200 (3)	0.0624 (13)
C12	−0.2097 (4)	0.4218 (3)	0.3869 (3)	0.0641 (13)
H12A	−0.2735	0.4074	0.4211	0.077*
C13	−0.2117 (4)	0.4043 (2)	0.3044 (3)	0.0540 (11)
H13A	−0.2776	0.3782	0.2831	0.065*
C14	−0.1180 (4)	0.4247 (2)	0.2518 (3)	0.0436 (10)
C15	−0.0206 (4)	0.4629 (2)	0.2838 (3)	0.0524 (11)
H15A	0.0431	0.4768	0.2492	0.063*
C16	−0.0166 (4)	0.4810 (3)	0.3674 (3)	0.0657 (13)
H16A	0.0501	0.5064	0.3886	0.079*
C17	0.0102 (3)	0.3235 (2)	0.0552 (2)	0.0416 (9)
C18	0.0034 (5)	0.3153 (3)	−0.0834 (3)	0.0739 (15)
H18A	−0.0274	0.3313	−0.1340	0.089*
C19	0.0845 (5)	0.2583 (3)	−0.0851 (3)	0.0763 (17)
H19A	0.1093	0.2366	−0.1346	0.092*
C20	0.1284 (5)	0.2342 (3)	−0.0089 (3)	0.0643 (13)
H20A	0.1845	0.1956	−0.0063	0.077*
C21	−0.1147 (4)	0.1532 (3)	0.1260 (4)	0.0726 (15)
H21A	−0.0726	0.1510	0.0761	0.087*
C22	−0.2264 (5)	0.1177 (3)	0.1312 (6)	0.102 (2)
H22A	−0.2596	0.0926	0.0862	0.123*
C23	−0.2840 (6)	0.1216 (4)	0.2044 (7)	0.123 (3)
H23A	−0.3606	0.1001	0.2086	0.148*
C24	−0.2353 (8)	0.1563 (5)	0.2753 (6)	0.1249 (18)
C25	−0.2921 (7)	0.1584 (4)	0.3481 (6)	0.1249 (18)
H25A	−0.3678	0.1362	0.3543	0.150*
C26	−0.2388 (8)	0.1930 (4)	0.4128 (6)	0.1249 (18)
H26A	−0.2788	0.1939	0.4636	0.150*
C27	−0.1208 (8)	0.2290 (5)	0.4057 (6)	0.116 (2)
C28	−0.0600 (11)	0.2649 (7)	0.4671 (5)	0.152 (4)
H28A	−0.0939	0.2655	0.5199	0.182*
C29	0.0518 (10)	0.3012 (6)	0.4548 (5)	0.130 (3)
H29A	0.0920	0.3252	0.4979	0.156*
C30	0.1011 (6)	0.2993 (4)	0.3709 (4)	0.099 (2)
H30A	0.1741	0.3233	0.3594	0.119*
C31	−0.0656 (5)	0.2289 (3)	0.3275 (3)	0.0754 (17)
C32	−0.1222 (5)	0.1917 (3)	0.2603 (4)	0.0717 (15)

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Ni1	0.0409 (2)	0.0465 (3)	0.0345 (2)	0.00456 (19)	−0.0015 (3)	0.0027 (3)
S1	0.0427 (4)	0.0406 (5)	0.0428 (5)	−0.0028 (3)	−0.0011 (5)	0.0020 (6)
S2	0.0396 (5)	0.0521 (6)	0.0437 (6)	0.0067 (4)	−0.0002 (4)	−0.0002 (5)
O1	0.0654 (18)	0.0592 (19)	0.0469 (19)	0.0048 (15)	0.0074 (15)	−0.0075 (15)
O2	0.0510 (14)	0.0504 (15)	0.065 (2)	−0.0131 (12)	−0.0083 (16)	−0.0006 (16)
O3	0.0397 (15)	0.125 (3)	0.059 (2)	−0.0106 (17)	−0.0056 (15)	−0.015 (2)
O4	0.102 (3)	0.0514 (19)	0.054 (2)	0.0244 (17)	0.0111 (17)	0.0098 (16)
N1	0.092 (3)	0.112 (4)	0.054 (3)	0.032 (3)	−0.011 (2)	0.016 (3)
N2	0.0408 (14)	0.0349 (15)	0.050 (2)	−0.0026 (11)	−0.0030 (18)	0.0058 (18)
N3	0.0485 (15)	0.0398 (16)	0.051 (2)	−0.0030 (13)	−0.008 (2)	0.003 (2)
N4	0.0402 (14)	0.0541 (18)	0.046 (2)	−0.0020 (13)	−0.0013 (19)	0.002 (2)
N5	0.109 (4)	0.156 (5)	0.052 (3)	−0.066 (4)	0.018 (3)	−0.027 (3)
N6	0.0463 (16)	0.0415 (17)	0.0346 (17)	0.0082 (14)	0.0002 (14)	−0.0013 (15)
N7	0.050 (2)	0.052 (2)	0.036 (2)	0.0120 (16)	0.0017 (16)	−0.0046 (17)
N8	0.069 (2)	0.068 (3)	0.037 (2)	0.019 (2)	−0.0056 (18)	0.0053 (18)
N9	0.0466 (16)	0.0558 (19)	0.068 (2)	0.0068 (14)	0.007 (3)	0.020 (3)
N10	0.083 (3)	0.076 (3)	0.041 (2)	0.030 (2)	−0.007 (2)	0.000 (2)
C1	0.061 (3)	0.050 (3)	0.054 (3)	0.006 (2)	−0.011 (2)	0.009 (2)
C2	0.065 (3)	0.050 (2)	0.045 (3)	0.002 (2)	0.008 (2)	0.003 (2)
C3	0.047 (2)	0.046 (2)	0.053 (3)	0.0064 (19)	0.0030 (19)	0.005 (2)
C4	0.0402 (19)	0.036 (2)	0.042 (2)	0.0011 (16)	−0.0010 (17)	−0.0020 (17)
C5	0.048 (2)	0.057 (3)	0.055 (3)	0.012 (2)	0.007 (2)	−0.003 (2)
C6	0.055 (3)	0.079 (3)	0.064 (3)	0.027 (3)	−0.005 (2)	0.004 (3)
C7	0.0430 (16)	0.0415 (19)	0.034 (2)	−0.0025 (14)	0.001 (2)	−0.001 (2)
C8	0.069 (2)	0.0370 (19)	0.070 (3)	−0.0032 (18)	−0.006 (3)	−0.001 (3)
C9	0.063 (2)	0.051 (2)	0.060 (3)	−0.0197 (18)	0.002 (3)	−0.004 (3)
C10	0.0466 (19)	0.063 (2)	0.048 (2)	−0.0135 (17)	−0.004 (3)	0.000 (3)
C11	0.070 (3)	0.072 (3)	0.045 (3)	−0.020 (2)	0.006 (2)	−0.009 (2)
C12	0.051 (2)	0.087 (4)	0.054 (3)	−0.027 (2)	0.011 (2)	−0.006 (3)
C13	0.045 (2)	0.062 (3)	0.055 (3)	−0.013 (2)	0.003 (2)	−0.007 (2)
C14	0.036 (2)	0.050 (3)	0.045 (2)	0.0035 (18)	0.0027 (17)	0.004 (2)
C15	0.047 (2)	0.057 (3)	0.053 (3)	−0.009 (2)	0.010 (2)	−0.002 (2)
C16	0.058 (3)	0.080 (4)	0.060 (3)	−0.029 (2)	0.007 (2)	−0.008 (3)
C17	0.045 (2)	0.041 (2)	0.038 (2)	0.0024 (16)	0.0008 (17)	0.0032 (18)
C18	0.074 (3)	0.110 (4)	0.037 (3)	0.023 (3)	−0.008 (2)	0.006 (3)
C19	0.086 (4)	0.110 (5)	0.033 (3)	0.027 (3)	0.005 (2)	−0.013 (3)
C20	0.065 (3)	0.076 (3)	0.052 (3)	0.021 (3)	0.002 (2)	−0.009 (3)
C21	0.057 (3)	0.062 (3)	0.100 (5)	−0.010 (2)	−0.010 (3)	−0.002 (3)
C22	0.064 (4)	0.076 (4)	0.168 (8)	−0.005 (3)	−0.011 (4)	0.013 (5)
C23	0.073 (4)	0.072 (4)	0.225 (11)	0.009 (3)	0.041 (6)	0.058 (6)
C24	0.113 (4)	0.126 (4)	0.136 (5)	−0.001 (3)	0.052 (3)	0.040 (4)
C25	0.113 (4)	0.126 (4)	0.136 (5)	−0.001 (3)	0.052 (3)	0.040 (4)
C26	0.113 (4)	0.126 (4)	0.136 (5)	−0.001 (3)	0.052 (3)	0.040 (4)
C27	0.127 (5)	0.134 (6)	0.087 (5)	0.030 (5)	0.030 (5)	0.037 (5)
C28	0.181 (10)	0.225 (12)	0.051 (5)	0.067 (9)	0.008 (6)	−0.001 (6)
C29	0.169 (9)	0.170 (9)	0.052 (5)	0.045 (8)	−0.022 (5)	−0.009 (5)
C30	0.117 (5)	0.130 (6)	0.051 (4)	0.047 (4)	−0.022 (3)	−0.020 (4)
C31	0.083 (4)	0.089 (4)	0.054 (3)	0.037 (3)	0.034 (3)	0.032 (3)
C32	0.069 (3)	0.066 (3)	0.080 (4)	0.020 (3)	0.017 (3)	0.032 (3)

Geometric parameters (Å, º) top

Ni1—N7	2.059 (4)	C5—H5C	0.9300
Ni1—N10	2.066 (4)	C6—H6A	0.9300
Ni1—N9	2.079 (3)	C8—C9	1.379 (5)
Ni1—N2	2.104 (3)	C8—H8A	0.9300
Ni1—N3	2.130 (3)	C9—C10	1.370 (5)
Ni1—N6	2.202 (3)	C9—H9A	0.9300
S1—O1	1.435 (3)	C10—H10A	0.9300
S1—O2	1.444 (2)	C11—C12	1.395 (6)
S1—N2	1.596 (3)	C11—C16	1.396 (6)
S1—C4	1.754 (4)	C12—C13	1.368 (6)
S2—O3	1.435 (3)	C12—H12A	0.9300
S2—O4	1.439 (3)	C13—C14	1.385 (5)
S2—N6	1.605 (3)	C13—H13A	0.9300
S2—C14	1.750 (4)	C14—C15	1.376 (6)
N1—C1	1.374 (6)	C15—C16	1.388 (6)
N1—H1B	0.8600	C15—H15A	0.9300
N1—H1A	0.8600	C16—H16A	0.9300
N2—C7	1.367 (4)	C18—C19	1.360 (7)
N3—C8	1.336 (4)	C18—H18A	0.9300
N3—C7	1.368 (4)	C19—C20	1.391 (7)
N4—C10	1.329 (4)	C19—H19A	0.9300
N4—C7	1.342 (4)	C20—H20A	0.9300
N5—C11	1.360 (6)	C21—C22	1.388 (7)
N5—H5A	0.8600	C21—H21A	0.9300
N5—H5B	0.8600	C22—C23	1.344 (11)
N6—C17	1.359 (5)	C22—H22A	0.9300
N7—C20	1.330 (6)	C23—C24	1.409 (12)
N7—C17	1.349 (5)	C23—H23A	0.9300
N8—C18	1.321 (6)	C24—C25	1.330 (11)
N8—C17	1.343 (5)	C24—C32	1.421 (10)
N9—C32	1.307 (7)	C25—C26	1.350 (11)
N9—C21	1.346 (7)	C25—H25A	0.9300
N10—C30	1.306 (7)	C26—C27	1.457 (12)
N10—C31	1.387 (7)	C26—H26A	0.9300
C1—C2	1.389 (6)	C27—C28	1.359 (13)
C1—C6	1.402 (6)	C27—C31	1.400 (9)
C2—C3	1.374 (6)	C28—C29	1.408 (13)
C2—H2A	0.9300	C28—H28A	0.9300
C3—C4	1.389 (6)	C29—C30	1.459 (10)
C3—H3A	0.9300	C29—H29A	0.9300
C4—C5	1.368 (5)	C30—H30A	0.9300
C5—C6	1.379 (6)	C31—C32	1.418 (8)

N7—Ni1—N10	163.95 (16)	N3—C8—H8A	119.7
N7—Ni1—N9	93.55 (19)	C9—C8—H8A	119.7
N10—Ni1—N9	79.7 (2)	C10—C9—C8	117.0 (3)
N7—Ni1—N2	96.67 (15)	C10—C9—H9A	121.5
N10—Ni1—N2	99.08 (17)	C8—C9—H9A	121.5
N9—Ni1—N2	103.64 (11)	N4—C10—C9	125.1 (3)
N7—Ni1—N3	90.95 (16)	N4—C10—H10A	117.5
N10—Ni1—N3	98.85 (19)	C9—C10—H10A	117.5
N9—Ni1—N3	166.70 (12)	N5—C11—C12	120.4 (4)
N2—Ni1—N3	63.36 (11)	N5—C11—C16	121.0 (4)
N7—Ni1—N6	62.52 (12)	C12—C11—C16	118.6 (4)
N10—Ni1—N6	102.74 (14)	C13—C12—C11	120.1 (4)
N9—Ni1—N6	90.91 (12)	C13—C12—H12A	119.9
N2—Ni1—N6	155.62 (13)	C11—C12—H12A	119.9
N3—Ni1—N6	102.27 (12)	C12—C13—C14	121.5 (4)
O1—S1—O2	115.96 (19)	C12—C13—H13A	119.2
O1—S1—N2	113.76 (19)	C14—C13—H13A	119.2
O2—S1—N2	104.49 (15)	C15—C14—C13	118.9 (4)
O1—S1—C4	108.17 (18)	C15—C14—S2	120.7 (3)
O2—S1—C4	107.61 (18)	C13—C14—S2	120.3 (3)
N2—S1—C4	106.3 (2)	C14—C15—C16	120.4 (4)
O3—S2—O4	114.6 (2)	C14—C15—H15A	119.8
O3—S2—N6	111.69 (19)	C16—C15—H15A	119.8
O4—S2—N6	111.68 (18)	C15—C16—C11	120.5 (4)
O3—S2—C14	108.4 (2)	C15—C16—H16A	119.8
O4—S2—C14	107.4 (2)	C11—C16—H16A	119.8
N6—S2—C14	102.18 (19)	N8—C17—N7	124.3 (4)
C1—N1—H1B	120.0	N8—C17—N6	125.9 (3)
C1—N1—H1A	120.0	N7—C17—N6	109.7 (3)
H1B—N1—H1A	120.0	N8—C18—C19	125.8 (5)
C7—N2—S1	123.2 (2)	N8—C18—H18A	117.1
C7—N2—Ni1	94.5 (2)	C19—C18—H18A	117.1
S1—N2—Ni1	140.89 (17)	C18—C19—C20	116.5 (5)
C8—N3—C7	117.4 (3)	C18—C19—H19A	121.8
C8—N3—Ni1	148.6 (3)	C20—C19—H19A	121.8
C7—N3—Ni1	93.3 (2)	N7—C20—C19	119.6 (4)
C10—N4—C7	114.2 (3)	N7—C20—H20A	120.2
C11—N5—H5A	120.0	C19—C20—H20A	120.2
C11—N5—H5B	120.0	N9—C21—C22	123.3 (6)
H5A—N5—H5B	120.0	N9—C21—H21A	118.3
C17—N6—S2	119.7 (3)	C22—C21—H21A	118.3
C17—N6—Ni1	90.3 (2)	C23—C22—C21	116.6 (8)
S2—N6—Ni1	145.00 (19)	C23—C22—H22A	121.7
C20—N7—C17	119.2 (4)	C21—C22—H22A	121.7
C20—N7—Ni1	143.5 (3)	C22—C23—C24	123.9 (7)
C17—N7—Ni1	96.9 (3)	C22—C23—H23A	118.1
C18—N8—C17	114.5 (4)	C24—C23—H23A	118.1
C32—N9—C21	118.2 (4)	C25—C24—C23	123.3 (9)
C32—N9—Ni1	113.6 (4)	C25—C24—C32	123.4 (10)
C21—N9—Ni1	127.9 (4)	C23—C24—C32	113.2 (7)
C30—N10—C31	120.5 (6)	C24—C25—C26	119.4 (9)
C30—N10—Ni1	128.2 (5)	C24—C25—H25A	120.3
C31—N10—Ni1	111.2 (4)	C26—C25—H25A	120.3
N1—C1—C2	120.2 (4)	C25—C26—C27	122.1 (8)
N1—C1—C6	122.3 (4)	C25—C26—H26A	118.9
C2—C1—C6	117.5 (4)	C27—C26—H26A	118.9
C3—C2—C1	120.5 (4)	C28—C27—C31	116.3 (8)
C3—C2—H2A	119.8	C28—C27—C26	126.4 (9)
C1—C2—H2A	119.8	C31—C27—C26	117.3 (9)
C2—C3—C4	121.5 (4)	C27—C28—C29	123.3 (8)
C2—C3—H3A	119.2	C27—C28—H28A	118.3
C4—C3—H3A	119.2	C29—C28—H28A	118.3
C5—C4—C3	118.5 (4)	C28—C29—C30	116.4 (8)
C5—C4—S1	122.1 (3)	C28—C29—H29A	121.8
C3—C4—S1	119.3 (3)	C30—C29—H29A	121.8
C4—C5—C6	120.7 (4)	N10—C30—C29	120.6 (8)
C4—C5—H5C	119.6	N10—C30—H30A	119.7
C6—C5—H5C	119.6	C29—C30—H30A	119.7
C5—C6—C1	121.3 (4)	N10—C31—C27	122.8 (7)
C5—C6—H6A	119.4	N10—C31—C32	117.3 (4)
C1—C6—H6A	119.4	C27—C31—C32	119.9 (7)
N4—C7—N2	125.7 (3)	N9—C32—C24	124.7 (7)
N4—C7—N3	125.5 (3)	N9—C32—C31	117.4 (5)
N2—C7—N3	108.8 (3)	C24—C32—C31	117.8 (7)
N3—C8—C9	120.7 (4)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1A···O1ⁱ	0.86	2.46	3.162 (6)	140
N1—H1B···O2ⁱⁱ	0.86	2.23	3.056 (6)	162
N5—H5A···O3ⁱⁱⁱ	0.86	2.52	3.285 (6)	148
N5—H5B···O4^iv	0.86	2.20	3.016 (6)	158
C5—H5C···O2^v	0.93	2.56	3.377 (5)	147
C12—H12A···N8ⁱⁱⁱ	0.93	2.56	3.470 (6)	166

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

Experimental details

Crystal data
Chemical formula	[Ni(C₁₀H₉N₄O₂S)₂(C₁₂H₈N₂)]
M_r	737.46
Crystal system, space group	Orthorhombic, Pca2₁
Temperature (K)	293
a, b, c (Å)	11.015 (2), 17.995 (3), 16.128 (3)
V (Å³)	3196.9 (10)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.79
Crystal size (mm)	0.34 × 0.26 × 0.18

Data collection
Diffractometer	Bruker SMART APEXII CCD area-detector diffractometer
Absorption correction	Multi-scan (ABSCOR; Higashi, 1995)
T_min, T_max	0.774, 0.870
No. of measured, independent and observed [I > 2σ(I)] reflections	27217, 7075, 5020
R_int	0.058
(sin θ/λ)_max (Å⁻¹)	0.651

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.044, 0.110, 1.02
No. of reflections	7075
No. of parameters	431
No. of restraints	2
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.51, −0.35
Absolute structure	Flack (1983), 3236 Friedel pairs
Absolute structure parameter	0.236 (16)

Computer programs: SMART (Bruker, 2001), SAINT (Bruker, 2001), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), SHELXTL (Sheldrick, 2008).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1A···O1ⁱ	0.8600	2.4556	3.162 (6)	139.59
N1—H1B···O2ⁱⁱ	0.8599	2.2262	3.056 (6)	161.95
N5—H5A···O3ⁱⁱⁱ	0.8601	2.5208	3.285 (6)	148.34
N5—H5B···O4^iv	0.8600	2.2025	3.016 (6)	157.46
C5—H5C···O2^v	0.9299	2.5598	3.377 (5)	146.85
C12—H12A···N8ⁱⁱⁱ	0.9300	2.5601	3.470 (6)	166.00

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

Acknowledgements

The work was supported by the Ningbo Natural Science Foundation (grant No. 2010 A610060), the Ningbo University Foundation (grant No. XK1066), the training funds of excellent theses for Masters in Ningbo University (grant Nos. PY20090012 and PY20100007) and the K. C. Wong Magna Fund in Ningbo University.

References

Bruker (2001). SAINT and SMART. Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
Ellena, J., Kremer, E., Facchin, G., Baran, E. J., Nascimento, O. R., Costa-Filho, A. J. & Torre, M. H. (2007). Polyhedron, 26, 3277–3285. Web of Science CSD CrossRef CAS Google Scholar
Flack, H. D. (1983). Acta Cryst. A39, 876–881. CrossRef CAS Web of Science IUCr Journals Google Scholar
Garcia-Raso, A., Fiol, J. J., Martorell, G., Lopez-Zafra, A. & Quiros, M. (1997). Polyhedron, 16, 613–621. CSD CrossRef CAS Web of Science Google Scholar
Garcia-Raso, A., Fiol, J. J., Rigo, S., López-López, A., Molins, E., Espinosa, E., Borras, E., Alzuet, G., Borras, J. & Castineiras, A. (2000). Polyhedron, 19, 991–1004. CAS Google Scholar
Golzar Hossain, G. M., Amoroso, A. J., Banu, A. & Malik, K. M. A. (2007). Polyhedron, 26, 967–974. Google Scholar
Gutierrez, L., Alzuet, G., Borras, J., Castineiras, A., Rodriguez-Fortea, A. & Ruiz, E. (2001). Inorg. Chem. 40, 3089–3096. Web of Science PubMed CAS Google Scholar
Higashi, T. (1995). ABSCOR. Rigaku Corporation, Tokyo, Japan. Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar

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Volume 68| Part 3| March 2012| Pages m348-m349

doi:10.1107/S1600536812008185

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

Bis[4-amino-N-(pyrimidin-2-yl)benzene­sulfonamidato](1,10-phenanthroline)nickel(II)

Related literature

Experimental

Crystal data

Data collection

Refinement

Supporting information

Acknowledgements

References

metal-organic compounds

Bis[4-amino-N-(pyrimidin-2-yl)benzenesulfonamidato](1,10-phenanthroline)nickel(II)