Diaqua-bis[4-(dimethyl-amino)benzoato-κO](isonicotinamide-κN)manganese(II).

The title Mn(II) complex, [Mn(C(9)H(10)NO(2))(2)(C(6)H(6)N(2)O)(H(2)O)(2)], contains two 4-(dimethylamino)benzoate (DMAB) anions, one isonicotinamide (INA) ligand and two coordinated water mol-ecules. One of the DMAB anions acts as a bidentate ligand, while the other is monodentate. The four O atoms in the equatorial plane around the Mn atom form a highly distorted square-planar arrangement, while the distorted octa-hedral coordination geometry is completed by the N atom of the INA ligand and the O atom of the second water mol-ecule in the axial positions. In the crystal structure, strong inter-molecular O-H⋯O, O-H⋯N and N-H⋯O hydrogen bonds link the mol-ecules into a two-dimensional network parallel to (010). Two weak C-H⋯π inter-actions are also found.

Related literature

For general backgroud, see: Adiwidjaja et al. (1978 ▶); Amiraslanov et al. (1979 ▶); Antolini et al. (1982 ▶); Antsyshkina et al. (1980 ▶); Bigoli et al. (1972 ▶); Catterick et al. (1974 ▶); Chen & Chen (2002 ▶); Hauptmann et al. (2000 ▶); Krishnamachari (1974 ▶); Shnulin et al. (1981 ▶). For related structures, see: Hökelek et al. (2009a ▶,b ▶,c ▶,d ▶,e ▶,f ▶,g ▶); Özbek et al. (2009 ▶); Tercan et al. (2009 ▶).

Experimental

Crystal data

[Mn(C9H10NO2)2(C6n class="Species">H6N2O)(H2O)2]

M = 541.46

Monoclinic,

a = 6.9120 (2) Å

b = 45.1365 (5) Å

c = 8.1506 (2) Å

β = 93.889 (1)°

V = 2537.0 (1) Å3

Z = 4

Mo Kα radiation

μ = 0.57 mm−1

T = 100 K

0.34 × 0.30 × 0.26 mm

Data collection

Bruker Kappa APEXII CCD area-detector diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2005 ▶) T min = 0.822, T max = 0.860

22933 measured reflections

6311 independent reflections

5980 reflections with I > 2σ(I)

R int = 0.025

Refinement

R[F 2 > 2σ(F 2)] = 0.074

wR(F 2) = 0.147

S = 1.38

6311 reflections

344 parameters

6 restraints

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.50 e Å−3

Δρmin = −1.15 e Å−3

Data collection: APEX2 (Bruker, 2007 ▶); cell refinement: SAINT (Bruker, 2007 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997 ▶); software used to prepare material for publication: WinGX (Farrugia, 1999 ▶).

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536809027093/dn2464sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536809027093/dn2464Isup2.hkl

Additional supplementary materials: crystallographic information; 3D view; checkCIF report

[Mn(C9H10NO2)2(C6H6N2O)(H2O)2]	F(000) = 1132
Mr = 541.46	Dx = 1.418 Mg m−3
Monoclinic, P21/n	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2yn	Cell parameters from 9856 reflections
a = 6.9120 (2) Å	θ = 2.6–28.4°
b = 45.1365 (5) Å	µ = 0.57 mm−1
c = 8.1506 (2) Å	T = 100 K
β = 93.889 (1)°	Block, colorless
V = 2537.0 (1) Å3	0.34 × 0.30 × 0.26 mm
Z = 4

Bruker Kappa APEXII CCD area-detector diffractometer	6311 independent reflections
Radiation source: fine-focus sealed tube	5980 reflections with I > 2σ(I)
graphite	Rint = 0.025
φ and ω scans	θmax = 28.5°, θmin = 1.8°
Absorption correction: multi-scan (SADABS; Bruker, 2005)	h = −9→8
Tmin = 0.822, Tmax = 0.860	k = −60→59
22933 measured reflections	l = −10→10

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)] = 0.074	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.147	H atoms treated by a mixture of independent and constrained refinement
S = 1.38	w = 1/[σ2(Fo2) + (0.P)2 + 9.0299P] where P = (Fo2 + 2Fc2)/3
6311 reflections	(Δ/σ)max < 0.001
344 parameters	Δρmax = 0.50 e Å−3
6 restraints	Δρmin = −1.15 e Å−3

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.

	x	y	z	Uiso*/Ueq
Mn1	0.89626 (8)	0.138233 (11)	0.52423 (6)	0.01186 (12)
O1	1.0707 (4)	0.16630 (6)	0.6803 (3)	0.0163 (5)
O2	1.3091 (4)	0.17803 (6)	0.5212 (3)	0.0168 (5)
O3	0.7933 (3)	0.09672 (5)	0.4009 (3)	0.0154 (5)
O4	1.0942 (4)	0.09799 (5)	0.5074 (3)	0.0145 (5)
O5	0.1617 (4)	0.11645 (6)	1.0883 (3)	0.0179 (5)
O6	1.0332 (4)	0.15667 (6)	0.3078 (3)	0.0154 (5)
H61	1.137 (5)	0.1657 (10)	0.363 (5)	0.034 (14)*
H62	1.081 (7)	0.1434 (9)	0.240 (5)	0.042 (15)*
O7	0.6603 (4)	0.16490 (6)	0.4240 (3)	0.0184 (5)
H71	0.694 (6)	0.1821 (6)	0.375 (5)	0.029 (13)*
H72	0.541 (3)	0.1671 (9)	0.452 (5)	0.024*
N1	0.7162 (4)	0.12666 (6)	0.7352 (3)	0.0132 (6)
N2	0.4078 (5)	0.10213 (7)	1.2669 (4)	0.0176 (6)
H2A	0.3322	0.0996	1.3453	0.021*
H2B	0.5301	0.0988	1.2834	0.021*
N3	1.6781 (4)	0.21772 (6)	1.2368 (4)	0.0145 (6)
N4	1.0784 (6)	−0.03194 (8)	0.1892 (5)	0.0333 (9)
C1	1.2368 (5)	0.17669 (7)	0.6597 (4)	0.0129 (6)
C2	1.3526 (5)	0.18809 (7)	0.8083 (4)	0.0126 (6)
C3	1.2728 (5)	0.18913 (8)	0.9603 (4)	0.0148 (6)
H3	1.1459	0.1827	0.9687	0.018*
C4	1.3773 (5)	0.19945 (8)	1.0992 (4)	0.0158 (7)
H4	1.3192	0.2003	1.1987	0.019*
C5	1.5709 (5)	0.20875 (7)	1.0916 (4)	0.0125 (6)
C6	1.6523 (5)	0.20724 (8)	0.9390 (4)	0.0153 (7)
H6	1.7804	0.2130	0.9307	0.018*
C7	1.5446 (5)	0.19722 (8)	0.8003 (4)	0.0158 (7)
H7	1.6014	0.1966	0.7001	0.019*
C8	0.9572 (5)	0.08403 (7)	0.4297 (4)	0.0131 (6)
C9	0.9864 (5)	0.05360 (8)	0.3708 (4)	0.0158 (7)
C10	1.1647 (6)	0.03925 (8)	0.4017 (5)	0.0199 (7)
H10	1.2647	0.0489	0.4623	0.024*
C11	1.1946 (6)	0.01099 (9)	0.3434 (5)	0.0245 (8)
H11	1.3143	0.0019	0.3657	0.029*
C12	1.0473 (7)	−0.00428 (8)	0.2511 (5)	0.0243 (8)
C13	0.8674 (6)	0.01007 (9)	0.2229 (5)	0.0248 (8)
H13	0.7664	0.0004	0.1639	0.030*
C14	0.8381 (6)	0.03848 (8)	0.2817 (5)	0.0203 (7)
H14	0.7180	0.0475	0.2613	0.024*
C15	0.7809 (5)	0.13009 (8)	0.8924 (4)	0.0161 (7)
H15	0.9075	0.1366	0.9153	0.019*
C16	0.6671 (5)	0.12440 (8)	1.0228 (4)	0.0157 (7)
H16	0.7181	0.1264	1.1308	0.019*
C17	0.4757 (5)	0.11571 (7)	0.9890 (4)	0.0129 (6)
C18	0.4073 (5)	0.11246 (7)	0.8254 (4)	0.0130 (6)
H18	0.2797	0.1068	0.7988	0.016*
C19	0.5315 (5)	0.11775 (8)	0.7038 (4)	0.0149 (6)
H19	0.4858	0.1150	0.5949	0.018*
C20	0.3358 (5)	0.11123 (7)	1.1209 (4)	0.0126 (6)
C21	1.5745 (6)	0.23707 (9)	1.3459 (5)	0.0230 (8)
H21A	1.6569	0.2415	1.4424	0.034*
H21B	1.4595	0.2272	1.3772	0.034*
H21C	1.5395	0.2552	1.2895	0.034*
C22	1.8760 (6)	0.22797 (9)	1.2178 (5)	0.0223 (8)
H22A	1.9377	0.2324	1.3239	0.033*
H22B	1.8725	0.2455	1.1506	0.033*
H22C	1.9476	0.2127	1.1663	0.033*
C23	0.9198 (8)	−0.04870 (10)	0.1085 (6)	0.0397 (12)
H23A	0.9672	−0.0675	0.0732	0.060*
H23B	0.8661	−0.0379	0.0148	0.060*
H23C	0.8211	−0.0519	0.1841	0.060*
C24	1.2663 (8)	−0.04584 (10)	0.2133 (7)	0.0429 (13)
H24A	1.2638	−0.0647	0.1583	0.064*
H24B	1.2976	−0.0487	0.3288	0.064*
H24C	1.3625	−0.0334	0.1690	0.064*

	U11	U22	U33	U12	U13	U23
Mn1	0.0110 (2)	0.0148 (2)	0.0100 (2)	−0.0003 (2)	0.00228 (17)	−0.00047 (19)
O1	0.0136 (12)	0.0213 (12)	0.0145 (12)	−0.0047 (10)	0.0052 (9)	−0.0037 (9)
O2	0.0117 (12)	0.0261 (13)	0.0127 (12)	−0.0010 (10)	0.0017 (9)	−0.0015 (10)
O3	0.0111 (11)	0.0195 (12)	0.0155 (12)	0.0009 (9)	−0.0003 (9)	−0.0026 (9)
O4	0.0144 (12)	0.0184 (12)	0.0106 (11)	0.0001 (9)	0.0008 (9)	−0.0019 (9)
O5	0.0137 (12)	0.0263 (13)	0.0136 (12)	0.0016 (10)	0.0012 (9)	−0.0031 (10)
O6	0.0128 (12)	0.0203 (12)	0.0135 (12)	0.0005 (10)	0.0047 (9)	0.0006 (9)
O7	0.0131 (12)	0.0230 (13)	0.0197 (13)	0.0048 (10)	0.0065 (10)	0.0062 (10)
N1	0.0142 (14)	0.0126 (13)	0.0130 (13)	0.0003 (11)	0.0024 (11)	0.0011 (10)
N2	0.0147 (14)	0.0267 (16)	0.0117 (14)	−0.0015 (12)	0.0022 (11)	0.0012 (11)
N3	0.0144 (14)	0.0161 (14)	0.0132 (13)	−0.0027 (11)	0.0021 (11)	−0.0017 (11)
N4	0.051 (2)	0.0158 (16)	0.034 (2)	0.0016 (16)	0.0109 (18)	−0.0041 (14)
C1	0.0110 (15)	0.0138 (15)	0.0140 (15)	0.0012 (12)	0.0013 (12)	−0.0011 (12)
C2	0.0154 (16)	0.0112 (14)	0.0112 (15)	−0.0013 (12)	0.0007 (12)	0.0003 (11)
C3	0.0125 (16)	0.0163 (16)	0.0158 (16)	−0.0007 (13)	0.0038 (12)	0.0003 (12)
C4	0.0183 (17)	0.0173 (16)	0.0121 (16)	−0.0019 (13)	0.0040 (13)	−0.0010 (12)
C5	0.0144 (16)	0.0108 (14)	0.0122 (15)	0.0017 (12)	0.0005 (12)	−0.0005 (11)
C6	0.0152 (16)	0.0174 (16)	0.0134 (16)	−0.0010 (13)	0.0021 (13)	−0.0003 (12)
C7	0.0143 (16)	0.0191 (16)	0.0145 (16)	0.0007 (13)	0.0043 (13)	−0.0004 (12)
C8	0.0148 (16)	0.0142 (15)	0.0108 (15)	0.0007 (12)	0.0044 (12)	0.0021 (12)
C9	0.0189 (17)	0.0140 (15)	0.0150 (16)	−0.0003 (13)	0.0036 (13)	0.0007 (12)
C10	0.0214 (19)	0.0175 (17)	0.0210 (18)	0.0015 (14)	0.0036 (14)	0.0010 (14)
C11	0.026 (2)	0.0191 (18)	0.029 (2)	0.0068 (15)	0.0057 (16)	0.0030 (15)
C12	0.039 (2)	0.0161 (17)	0.0192 (18)	0.0007 (16)	0.0100 (16)	0.0006 (14)
C13	0.032 (2)	0.0189 (18)	0.024 (2)	−0.0049 (16)	0.0060 (16)	−0.0034 (15)
C14	0.0223 (19)	0.0186 (17)	0.0205 (18)	0.0003 (14)	0.0046 (14)	−0.0028 (14)
C15	0.0104 (15)	0.0208 (17)	0.0170 (16)	−0.0004 (13)	0.0005 (12)	0.0011 (13)
C16	0.0171 (17)	0.0181 (16)	0.0115 (15)	−0.0005 (13)	−0.0018 (12)	−0.0011 (12)
C17	0.0166 (16)	0.0108 (14)	0.0118 (15)	0.0012 (12)	0.0046 (12)	0.0001 (11)
C18	0.0117 (15)	0.0137 (15)	0.0136 (15)	−0.0022 (12)	−0.0002 (12)	−0.0010 (12)
C19	0.0166 (17)	0.0165 (16)	0.0113 (15)	0.0000 (13)	0.0002 (12)	−0.0012 (12)
C20	0.0140 (16)	0.0149 (15)	0.0091 (14)	−0.0016 (12)	0.0020 (12)	−0.0025 (11)
C21	0.025 (2)	0.0225 (19)	0.0216 (19)	−0.0009 (15)	0.0046 (15)	−0.0104 (14)
C22	0.0181 (18)	0.030 (2)	0.0183 (18)	−0.0063 (15)	0.0007 (14)	−0.0033 (15)
C23	0.059 (3)	0.018 (2)	0.044 (3)	−0.010 (2)	0.020 (2)	−0.0083 (18)
C24	0.062 (4)	0.020 (2)	0.048 (3)	0.012 (2)	0.018 (3)	−0.0008 (19)

Mn1—O1	2.114 (2)	C7—C2	1.395 (5)
Mn1—O3	2.221 (2)	C7—H7	0.9300
Mn1—O4	2.284 (2)	C8—C9	1.473 (5)
Mn1—O6	2.219 (2)	C9—C10	1.400 (5)
Mn1—O7	2.144 (3)	C10—H10	0.9300
Mn1—N1	2.252 (3)	C11—C10	1.381 (5)
Mn1—C8	2.608 (3)	C11—C12	1.405 (6)
O1—C1	1.261 (4)	C11—H11	0.9300
O2—C1	1.267 (4)	C13—C12	1.408 (6)
O3—C8	1.277 (4)	C13—H13	0.9300
O4—C8	1.270 (4)	C14—C9	1.394 (5)
O5—C20	1.238 (4)	C14—C13	1.388 (5)
O6—H61	0.92 (4)	C14—H14	0.9300
O6—H62	0.89 (4)	C15—C16	1.388 (5)
O7—H71	0.909 (17)	C15—H15	0.9300
O7—H72	0.876 (19)	C16—H16	0.9300
N1—C15	1.337 (4)	C17—C16	1.389 (5)
N2—C20	1.324 (4)	C17—C18	1.392 (5)
N2—H2A	0.8600	C17—C20	1.507 (5)
N2—H2B	0.8600	C18—H18	0.9300
N3—C5	1.412 (4)	C19—N1	1.346 (4)
N3—C21	1.467 (5)	C19—C18	1.376 (5)
N3—C22	1.462 (5)	C19—H19	0.9300
N4—C12	1.369 (5)	C21—H21A	0.9600
N4—C23	1.453 (6)	C21—H21B	0.9600
N4—C24	1.444 (7)	C21—H21C	0.9600
C1—C2	1.497 (5)	C22—H22A	0.9600
C3—C2	1.391 (5)	C22—H22B	0.9600
C3—C4	1.382 (5)	C22—H22C	0.9600
C3—H3	0.9300	C23—H23A	0.9600
C4—H4	0.9300	C23—H23B	0.9600
C5—C4	1.407 (5)	C23—H23C	0.9600
C5—C6	1.401 (5)	C24—H24A	0.9600
C6—C7	1.387 (5)	C24—H24B	0.9600
C6—H6	0.9300	C24—H24C	0.9600
O1—Mn1—O3	158.49 (10)	O4—C8—O3	119.4 (3)
O1—Mn1—O4	101.13 (9)	O4—C8—C9	120.7 (3)
O1—Mn1—O6	89.82 (10)	O4—C8—Mn1	61.14 (17)
O1—Mn1—O7	106.33 (11)	C9—C8—Mn1	177.8 (3)
O1—Mn1—N1	90.10 (10)	C10—C9—C8	120.8 (3)
O1—Mn1—C8	130.01 (11)	C14—C9—C8	120.9 (3)
O3—Mn1—O4	58.45 (9)	C14—C9—C10	118.3 (3)
O3—Mn1—N1	88.47 (10)	C9—C10—H10	119.5
O3—Mn1—C8	29.30 (10)	C11—C10—C9	121.1 (4)
O4—Mn1—C8	29.15 (10)	C11—C10—H10	119.5
O6—Mn1—O3	95.59 (9)	C10—C11—C12	121.2 (4)
O6—Mn1—O4	87.77 (9)	C10—C11—H11	119.4
O6—Mn1—N1	168.98 (10)	C12—C11—H11	119.4
O6—Mn1—C8	91.77 (10)	N4—C12—C11	121.2 (4)
O7—Mn1—O3	95.10 (10)	N4—C12—C13	121.2 (4)
O7—Mn1—O4	150.12 (10)	C11—C12—C13	117.5 (3)
O7—Mn1—O6	80.84 (9)	C12—C13—H13	119.5
O7—Mn1—N1	88.61 (10)	C14—C13—C12	121.1 (4)
O7—Mn1—C8	123.23 (11)	C14—C13—H13	119.5
N1—Mn1—O4	103.05 (9)	C9—C14—H14	119.6
N1—Mn1—C8	96.71 (10)	C13—C14—C9	120.9 (4)
C1—O1—Mn1	129.0 (2)	C13—C14—H14	119.6
C8—O3—Mn1	92.4 (2)	N1—C15—C16	122.8 (3)
C8—O4—Mn1	89.7 (2)	N1—C15—H15	118.6
Mn1—O6—H61	98 (3)	C16—C15—H15	118.6
Mn1—O6—H62	116 (3)	C15—C16—C17	118.8 (3)
H61—O6—H62	107 (3)	C15—C16—H16	120.6
Mn1—O7—H71	116 (3)	C17—C16—H16	120.6
Mn1—O7—H72	132 (3)	C16—C17—C18	118.4 (3)
H71—O7—H72	107 (3)	C16—C17—C20	123.0 (3)
C15—N1—Mn1	122.6 (2)	C18—C17—C20	118.4 (3)
C15—N1—C19	117.9 (3)	C17—C18—H18	120.5
C19—N1—Mn1	119.4 (2)	C19—C18—C17	118.9 (3)
C20—N2—H2A	120.0	C19—C18—H18	120.5
C20—N2—H2B	120.0	N1—C19—C18	123.0 (3)
H2A—N2—H2B	120.0	N1—C19—H19	118.5
C5—N3—C21	115.4 (3)	C18—C19—H19	118.5
C5—N3—C22	116.3 (3)	O5—C20—N2	123.6 (3)
C22—N3—C21	112.0 (3)	O5—C20—C17	118.9 (3)
C12—N4—C23	120.6 (4)	N2—C20—C17	117.6 (3)
C12—N4—C24	120.6 (4)	N3—C21—H21A	109.5
C24—N4—C23	118.7 (4)	N3—C21—H21B	109.5
O1—C1—O2	123.6 (3)	N3—C21—H21C	109.5
O1—C1—C2	117.5 (3)	H21A—C21—H21B	109.5
O2—C1—C2	118.9 (3)	H21A—C21—H21C	109.5
C3—C2—C1	120.6 (3)	H21B—C21—H21C	109.5
C3—C2—C7	117.9 (3)	N3—C22—H22A	109.5
C7—C2—C1	121.5 (3)	N3—C22—H22B	109.5
C2—C3—H3	119.2	N3—C22—H22C	109.5
C4—C3—C2	121.6 (3)	H22A—C22—H22B	109.5
C4—C3—H3	119.2	H22A—C22—H22C	109.5
C3—C4—C5	120.7 (3)	H22B—C22—H22C	109.5
C3—C4—H4	119.7	N4—C23—H23A	109.5
C5—C4—H4	119.7	N4—C23—H23B	109.5
C4—C5—N3	119.7 (3)	N4—C23—H23C	109.5
C6—C5—C4	117.7 (3)	H23A—C23—H23B	109.5
C6—C5—N3	122.6 (3)	H23A—C23—H23C	109.5
C5—C6—H6	119.5	H23B—C23—H23C	109.5
C7—C6—C5	120.9 (3)	N4—C24—H24A	109.5
C7—C6—H6	119.5	N4—C24—H24B	109.5
C2—C7—H7	119.4	N4—C24—H24C	109.5
C6—C7—C2	121.2 (3)	H24A—C24—H24B	109.5
C6—C7—H7	119.4	H24A—C24—H24C	109.5
O3—C8—C9	119.8 (3)	H24B—C24—H24C	109.5
O3—C8—Mn1	58.31 (17)
O3—Mn1—O1—C1	76.6 (4)	C21—N3—C5—C6	139.4 (3)
O4—Mn1—O1—C1	59.4 (3)	C22—N3—C5—C4	−178.1 (3)
O6—Mn1—O1—C1	−28.3 (3)	C22—N3—C5—C6	5.3 (5)
O7—Mn1—O1—C1	−108.7 (3)	C23—N4—C12—C11	173.7 (4)
N1—Mn1—O1—C1	162.7 (3)	C23—N4—C12—C13	−7.1 (6)
C8—Mn1—O1—C1	63.9 (3)	C24—N4—C12—C11	−1.9 (6)
O1—Mn1—O3—C8	−20.3 (4)	C24—N4—C12—C13	177.3 (4)
O4—Mn1—O3—C8	−0.29 (18)	O1—C1—C2—C3	−4.8 (5)
O6—Mn1—O3—C8	83.6 (2)	O1—C1—C2—C7	173.5 (3)
O7—Mn1—O3—C8	164.89 (19)	O2—C1—C2—C3	175.0 (3)
N1—Mn1—O3—C8	−106.6 (2)	O2—C1—C2—C7	−6.7 (5)
O1—Mn1—O4—C8	172.96 (19)	C4—C3—C2—C1	179.7 (3)
O3—Mn1—O4—C8	0.29 (18)	C4—C3—C2—C7	1.4 (5)
O6—Mn1—O4—C8	−97.66 (19)	C2—C3—C4—C5	−1.3 (5)
O7—Mn1—O4—C8	−30.5 (3)	N3—C5—C4—C3	−176.6 (3)
N1—Mn1—O4—C8	80.2 (2)	C6—C5—C4—C3	0.2 (5)
O1—Mn1—N1—C15	−20.9 (3)	N3—C5—C6—C7	177.4 (3)
O1—Mn1—N1—C19	154.6 (3)	C4—C5—C6—C7	0.7 (5)
O3—Mn1—N1—C15	137.6 (3)	C5—C6—C7—C2	−0.6 (5)
O3—Mn1—N1—C19	−46.9 (3)	C6—C7—C2—C1	−178.8 (3)
O4—Mn1—N1—C15	80.5 (3)	C6—C7—C2—C3	−0.5 (5)
O4—Mn1—N1—C19	−103.9 (3)	O3—C8—C9—C10	−179.8 (3)
O6—Mn1—N1—C15	−110.5 (5)	O3—C8—C9—C14	0.9 (5)
O6—Mn1—N1—C19	65.1 (6)	O4—C8—C9—C10	1.1 (5)
O7—Mn1—N1—C15	−127.3 (3)	O4—C8—C9—C14	−178.3 (3)
O7—Mn1—N1—C19	48.3 (3)	C8—C9—C10—C11	−178.4 (3)
C8—Mn1—N1—C15	109.4 (3)	C14—C9—C10—C11	0.9 (5)
C8—Mn1—N1—C19	−75.0 (3)	C12—C11—C10—C9	0.1 (6)
O1—Mn1—C8—O3	170.45 (17)	C10—C11—C12—N4	178.1 (4)
O1—Mn1—C8—O4	−9.0 (2)	C10—C11—C12—C13	−1.1 (6)
O3—Mn1—C8—O4	−179.5 (3)	C14—C13—C12—N4	−178.1 (4)
O4—Mn1—C8—O3	179.5 (3)	C14—C13—C12—C11	1.2 (6)
O6—Mn1—C8—O3	−98.29 (19)	C9—C14—C13—C12	−0.1 (6)
O6—Mn1—C8—O4	82.22 (19)	C13—C14—C9—C8	178.4 (3)
O7—Mn1—C8—O3	−18.1 (2)	C13—C14—C9—C10	−0.9 (5)
O7—Mn1—C8—O4	162.42 (17)	N1—C15—C16—C17	−2.2 (5)
N1—Mn1—C8—O3	74.7 (2)	C18—C17—C16—C15	1.3 (5)
N1—Mn1—C8—O4	−104.83 (19)	C20—C17—C16—C15	−175.3 (3)
Mn1—O1—C1—O2	18.6 (5)	C16—C17—C18—C19	0.5 (5)
Mn1—O1—C1—C2	−161.6 (2)	C20—C17—C18—C19	177.2 (3)
Mn1—O3—C8—O4	0.5 (3)	C16—C17—C20—O5	148.3 (3)
Mn1—O3—C8—C9	−178.7 (3)	C16—C17—C20—N2	−31.0 (5)
Mn1—O4—C8—O3	−0.5 (3)	C18—C17—C20—O5	−28.3 (5)
Mn1—O4—C8—C9	178.7 (3)	C18—C17—C20—N2	152.4 (3)
Mn1—N1—C15—C16	176.7 (3)	C18—C19—N1—Mn1	−174.9 (3)
C19—N1—C15—C16	1.1 (5)	C18—C19—N1—C15	0.9 (5)
C21—N3—C5—C4	−43.9 (4)	N1—C19—C18—C17	−1.6 (5)

D—H···A	D—H	H···A	D···A	D—H···A
N2—H2A···O4i	0.86	2.18	3.025 (4)	167
N2—H2B···O3ii	0.86	2.00	2.821 (4)	159
O6—H61···O2	0.92 (4)	1.78 (4)	2.672 (4)	162 (4)
O6—H62···O5iii	0.89 (4)	1.85 (4)	2.739 (4)	175 (4)
O7—H71···N3iv	0.91 (2)	1.96 (2)	2.838 (2)	161 (2)
O7—H72···O2v	0.88 (2)	1.80 (2)	2.671 (2)	170 (2)
C23—H23B···Cg2vi	0.96	2.90	3.649 (4)	136
C24—H24A···Cg3vii	0.96	2.74	3.594 (3)	149

Compound	C1—O1	C1—O2	C8—O3	C8—O4
Ia	1.261 (4)	1.267 (4)	1.277 (4)	1.270 (4)
IIb	1.244 (4)	1.270 (4)
IIIc	1.284 (2)	1.248 (2)
	1.278 (2)	1.241 (2)
IVd	1.267 (3)	1.258 (3)
Ve	1.263 (2)	1.240 (2)
VIf	1.2611 (17)	1.2396 (19)
VIIg	1.2616 (17)	1.2435 (18)
VIIIh	1.2746 (18)	1.2675 (17)
IXi	1.2682 (17)	1.2628 (17)	1.2743 (18)	1.2716 (18)
Xj	1.265 (3)	1.265 (3)	1.278 (3)	1.271 (3)

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N2—H2A⋯O4i	0.86	2.18	3.025 (4)	167
N2—H2B⋯O3ii	0.86	2.00	2.821 (4)	159
O6—H61⋯O2	0.92 (4)	1.78 (4)	2.672 (4)	162 (4)
O6—H62⋯O5iii	0.89 (4)	1.85 (4)	2.739 (4)	175 (4)
O7—H71⋯N3iv	0.91 (2)	1.96 (2)	2.838 (2)	161 (2)
O7—H72⋯O2v	0.88 (2)	1.80 (2)	2.671 (2)	170 (2)
C23—H23B⋯Cg2vi	0.96	2.90	3.649 (4)	136
C24—H24A⋯Cg3vii	0.96	2.74	3.594 (3)	149

Symmetry codes: (i) ; (ii) ; (iii) ; (iv) ; (v) ; (vi) ; (vii) . Cg2 and Cg3 are centroids of the C9–C14 and N1/C15–C19 rings, respectively.

Table 2

Comparison of the carboxylate bonds (Å) in the title compound with the corresponding values in related compounds

Compound	C1—O1	C1—O2	C8—O3	C8—O4
Ia	1.261 (4)	1.267 (4)	1.277 (4)	1.270 (4)
IIb	1.244 (4)	1.270 (4)
IIIc	1.284 (2)	1.248 (2)
	1.278 (2)	1.241 (2)
IVd	1.267 (3)	1.258 (3)
Ve	1.263 (2)	1.240 (2)
VIf	1.2611 (17)	1.2396 (19)
VIIg	1.2616 (17)	1.2435 (18)
VIIIh	1.2746 (18)	1.2675 (17)
IXi	1.2682 (17)	1.2628 (17)	1.2743 (18)	1.2716 (18)
Xj	1.265 (3)	1.265 (3)	1.278 (3)	1.271 (3)

Notes: (a) this work; (b) [Co(NA)2(H2O)4](C7H4FO2)2 (Özbek et al., 2009 ▶); (c) [Zn(NA)2C8H8NO2)2] (Tercan et al., 2009 ▶); (d) [Ni(NA)2(C7H4ClO2)2(H2O)2] (Hökelek et al., 2009a ▶); (e) [Zn(DENA)2(C7H4BrO2)2(H2O)2] (Hökelek et al., 2009b ▶); (f) [Mn(DENA)2(C7H4BrO2)2(H2O)2] (Hökelek et al., 2009c ▶); (g) [Ni(DENA)2(C7H4(ClO2)2(H2O)2] (Hökelek et al., 2009d ▶); (h) [Ni(NA)2(C8H8NO2)2(H2O)2] (Hökelek et al., 2009e ▶); (i) [Co(NA)2(C9H10NO2)2(H2O)2] (Hökelek et al., 2009f ▶); (j) [Zn(NA)2((C9H10NO2)2(H2O)2] (Hökelek et al., 2009g ▶).