Aqua­(2,9-dimethyl-1,10-phenanthroline-κ2N,N′)dinitratocobalt(II)

Ding, C.-F.; Zhang, M.-L.; Li, X.-M.; Zhang, S.-S.

doi:10.1107/S1600536806036476

Aqua(2,9-dimethyl-1,10-phenanthroline-κ²N,N′)dinitratocobalt(II)

C.-F. Ding, M.-L. Zhang, X.-M. Li and S.-S. Zhang

In the title compound, [Co(NO₃)₂(C₁₄H₁₂N₂)(H₂O)], the Co^II atom is coordinated by a bidentate 2,9-dimethyl-1,10-phenanthroline ligand, two nitrate ligands and one water molecule in a distorted octahedral environment. One of the nitrate ligands chelates in a bidentate manner and the other is monodentate. The molecule is stabilized by O—H

O hydrogen bonds involving water molecules and by C—H

O hydrogen bonds to form a two-dimensional network. The packing is further stablized by π–π interactions.

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Supporting information

	Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536806036476/ym2013sup1.cif Contains datablocks global, I
	Structure factor file (CIF format) https://doi.org/10.1107/S1600536806036476/ym2013Isup2.hkl Contains datablock I

CCDC reference: 625057

checkCIF report

Key indicators

Single-crystal X-ray study
T = 293 K
Mean (C-C) = 0.005 Å
R factor = 0.044
wR factor = 0.119
Data-to-parameter ratio = 14.0

checkCIF/PLATON results

No syntax errors found



Alert level B
PLAT232_ALERT_2_B Hirshfeld Test Diff (M-X)  Co1    -   O1      ..      21.92 su
PLAT232_ALERT_2_B Hirshfeld Test Diff (M-X)  Co1    -   O6      ..      19.40 su
PLAT241_ALERT_2_B Check High      Ueq as Compared to Neighbors for         O1

Alert level C
PLAT232_ALERT_2_C Hirshfeld Test Diff (M-X)  Co1    -   O5      ..       9.77 su
PLAT241_ALERT_2_C Check High      Ueq as Compared to Neighbors for         O5
PLAT241_ALERT_2_C Check High      Ueq as Compared to Neighbors for         O6
PLAT242_ALERT_2_C Check Low       Ueq as Compared to Neighbors for        Co1
PLAT242_ALERT_2_C Check Low       Ueq as Compared to Neighbors for         N3
PLAT242_ALERT_2_C Check Low       Ueq as Compared to Neighbors for         N4
PLAT380_ALERT_4_C Check Incorrectly? Oriented X(sp2)-Methyl Moiety         C1
PLAT710_ALERT_4_C Delete 1-2-3 or 2-3-4 Linear Torsion Angle ... #          8
            N2  -CO1 -O5  -N4     20.00  0.70   1.555   1.555   1.555   1.555
PLAT710_ALERT_4_C Delete 1-2-3 or 2-3-4 Linear Torsion Angle ... #         28
            O5  -CO1 -N2  -C11   -28.60  0.70   1.555   1.555   1.555   1.555
PLAT710_ALERT_4_C Delete 1-2-3 or 2-3-4 Linear Torsion Angle ... #         33
            O5  -CO1 -N2  -C12   151.80  0.50   1.555   1.555   1.555   1.555
PLAT720_ALERT_4_C Number of Unusual/Non-Standard Label(s) ........          2

Alert level G
PLAT199_ALERT_1_G Check the Reported _cell_measurement_temperature        293 K
PLAT200_ALERT_1_G Check the Reported _diffrn_ambient_temperature .        293 K

   0 ALERT level A = In general: serious problem
   3 ALERT level B = Potentially serious problem
  11 ALERT level C = Check and explain
   2 ALERT level G = General alerts; check

   2 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
   9 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
   5 ALERT type 4 Improvement, methodology, query or suggestion
   0 ALERT type 5 Informative message, check

Computing details top

Data collection: SMART (Siemens, 1996); cell refinement: SAINT (Siemens, 1996); data reduction: SAINT; program(s) used to solve structure: SHELXTL (Sheldrick, 1997); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL, PARST (Nardelli, 1995) and PLATON (Spek, 2003).

Aqua(2,9-dimethyl-1,10-phenanthroline-κ²N,N')dinitratocobalt(II) top

Crystal data top

[Co(NO₃)₂(C₁₄H₁₂N₂)(H₂O)]	F(000) = 836
M_r = 409.22	D_x = 1.633 Mg m⁻³
Monoclinic, P2₁/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 2633 reflections
a = 11.1392 (10) Å	θ = 2.4–24.0°
b = 10.8081 (10) Å	µ = 1.08 mm⁻¹
c = 15.0542 (10) Å	T = 293 K
β = 113.287 (5)°	Plate, brown
V = 1664.8 (2) Å³	0.28 × 0.20 × 0.08 mm
Z = 4

Data collection top

Siemens SMART 1000 CCD area-detector diffractometer	3287 independent reflections
Radiation source: fine-focus sealed tube	2650 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.025
Detector resolution: 8.33 pixels mm^-1	θ_max = 26.0°, θ_min = 2.0°
ω scans	h = −13→13
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	k = −13→12
T_min = 0.752, T_max = 0.918	l = −15→18
9118 measured reflections

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)] = 0.044	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.119	H-atom parameters constrained
S = 1.03	w = 1/[σ²(F_o²) + (0.0683P)² + 0.3288P] where P = (F_o² + 2F_c²)/3
3287 reflections	(Δ/σ)_max < 0.001
235 parameters	Δρ_max = 0.40 e Å⁻³
0 restraints	Δρ_min = −0.30 e Å⁻³

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
Co1	0.31409 (4)	0.28228 (3)	0.53980 (3)	0.04265 (16)
O1W	0.3765 (2)	0.27633 (19)	0.42755 (17)	0.0604 (6)
H1W1	0.3496	0.2309	0.3801	0.072*
H2W1	0.4196	0.3314	0.4168	0.072*
O1	0.2112 (3)	0.3756 (3)	0.62011 (17)	0.0905 (9)
O2	0.3243 (4)	0.2367 (3)	0.7099 (3)	0.1027 (11)
O3	0.2098 (2)	0.3527 (2)	0.76138 (15)	0.0640 (6)
O4	0.6062 (2)	0.4992 (3)	0.65643 (18)	0.0838 (8)
O5	0.5106 (2)	0.3218 (2)	0.63445 (18)	0.0722 (7)
O6	0.4037 (2)	0.4780 (2)	0.55733 (16)	0.0662 (6)
N1	0.2886 (2)	0.0884 (2)	0.52961 (16)	0.0453 (6)
N2	0.1199 (2)	0.2695 (2)	0.43410 (16)	0.0414 (5)
N3	0.2491 (3)	0.3223 (3)	0.6986 (2)	0.0570 (7)
N4	0.5087 (3)	0.4352 (3)	0.61667 (19)	0.0575 (7)
C1	0.5059 (3)	0.0383 (3)	0.6464 (3)	0.0746 (10)
H1A	0.5116	0.1269	0.6486	0.112*
H1B	0.5710	0.0053	0.6261	0.112*
H1C	0.5204	0.0071	0.7096	0.112*
C2	0.3741 (3)	0.0003 (3)	0.5768 (2)	0.0561 (8)
C3	0.3409 (4)	−0.1261 (3)	0.5606 (3)	0.0735 (10)
H3A	0.4017	−0.1862	0.5940	0.088*
C4	0.2218 (4)	−0.1601 (3)	0.4971 (3)	0.0742 (10)
H4A	0.2007	−0.2436	0.4869	0.089*
C5	0.1285 (3)	−0.0701 (3)	0.4459 (2)	0.0560 (8)
C6	−0.0004 (4)	−0.0983 (3)	0.3787 (3)	0.0666 (9)
H6A	−0.0263	−0.1805	0.3663	0.080*
C7	−0.0850 (4)	−0.0081 (4)	0.3332 (2)	0.0648 (9)
H7A	−0.1692	−0.0288	0.2905	0.078*
C8	−0.0486 (3)	0.1190 (3)	0.3490 (2)	0.0520 (7)
C9	−0.1311 (3)	0.2179 (3)	0.3025 (2)	0.0646 (9)
H9A	−0.2159	0.2020	0.2588	0.078*
C10	−0.0886 (3)	0.3361 (4)	0.3207 (2)	0.0618 (8)
H10A	−0.1438	0.4010	0.2890	0.074*
C11	0.0397 (3)	0.3608 (3)	0.3878 (2)	0.0493 (7)
C12	0.0773 (3)	0.1497 (3)	0.41496 (19)	0.0431 (6)
C13	0.1672 (3)	0.0539 (3)	0.4648 (2)	0.0445 (7)
C14	0.0896 (3)	0.4911 (3)	0.4076 (2)	0.0601 (8)
H14A	0.1777	0.4907	0.4552	0.090*
H14B	0.0353	0.5382	0.4312	0.090*
H14C	0.0876	0.5278	0.3489	0.090*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Co1	0.0383 (2)	0.0412 (2)	0.0445 (3)	−0.00496 (15)	0.01209 (18)	−0.00244 (16)
O1W	0.0680 (15)	0.0595 (13)	0.0629 (14)	−0.0127 (11)	0.0358 (12)	−0.0084 (10)
O1	0.0813 (19)	0.144 (3)	0.0431 (14)	−0.0107 (18)	0.0210 (13)	0.0050 (15)
O2	0.125 (3)	0.0747 (18)	0.138 (3)	0.0110 (18)	0.084 (3)	−0.0145 (18)
O3	0.0691 (15)	0.0822 (16)	0.0488 (13)	0.0075 (12)	0.0320 (12)	0.0003 (11)
O4	0.0684 (17)	0.0887 (18)	0.0704 (16)	−0.0432 (15)	0.0021 (13)	0.0000 (14)
O5	0.0640 (16)	0.0641 (15)	0.0710 (16)	−0.0193 (12)	0.0082 (12)	0.0101 (12)
O6	0.0580 (15)	0.0698 (15)	0.0596 (14)	−0.0033 (12)	0.0113 (12)	−0.0044 (12)
N1	0.0484 (15)	0.0429 (13)	0.0467 (14)	0.0004 (10)	0.0212 (12)	−0.0011 (10)
N2	0.0395 (13)	0.0473 (13)	0.0369 (12)	−0.0054 (10)	0.0145 (11)	−0.0031 (10)
N3	0.0577 (17)	0.0647 (17)	0.0521 (16)	−0.0223 (14)	0.0254 (14)	−0.0146 (13)
N4	0.0534 (17)	0.0666 (18)	0.0477 (15)	−0.0207 (14)	0.0148 (13)	−0.0032 (13)
C1	0.061 (2)	0.064 (2)	0.086 (3)	0.0188 (18)	0.0162 (19)	0.0120 (19)
C2	0.057 (2)	0.0481 (17)	0.068 (2)	0.0069 (15)	0.0301 (17)	0.0016 (15)
C3	0.078 (3)	0.0455 (18)	0.103 (3)	0.0107 (18)	0.043 (2)	0.0078 (19)
C4	0.091 (3)	0.0424 (18)	0.103 (3)	−0.0090 (19)	0.054 (2)	−0.0086 (19)
C5	0.069 (2)	0.0495 (17)	0.0604 (19)	−0.0126 (16)	0.0379 (17)	−0.0103 (14)
C6	0.077 (2)	0.058 (2)	0.073 (2)	−0.0326 (18)	0.038 (2)	−0.0230 (18)
C7	0.060 (2)	0.079 (2)	0.055 (2)	−0.0326 (19)	0.0223 (17)	−0.0195 (18)
C8	0.0460 (17)	0.069 (2)	0.0422 (16)	−0.0159 (15)	0.0183 (13)	−0.0067 (14)
C9	0.0456 (19)	0.090 (3)	0.0478 (19)	−0.0160 (18)	0.0069 (14)	−0.0030 (17)
C10	0.0471 (18)	0.078 (2)	0.0497 (18)	0.0011 (17)	0.0083 (14)	0.0085 (17)
C11	0.0458 (17)	0.0592 (18)	0.0412 (16)	0.0001 (14)	0.0154 (13)	0.0035 (13)
C12	0.0461 (16)	0.0514 (16)	0.0376 (14)	−0.0112 (13)	0.0229 (13)	−0.0062 (12)
C13	0.0513 (18)	0.0458 (15)	0.0432 (16)	−0.0100 (13)	0.0261 (14)	−0.0074 (12)
C14	0.060 (2)	0.0550 (18)	0.057 (2)	0.0024 (15)	0.0136 (16)	0.0070 (15)

Geometric parameters (Å, º) top

Co1—O1W	2.067 (2)	C2—C3	1.412 (5)
Co1—N1	2.112 (2)	C3—C4	1.343 (5)
Co1—N2	2.124 (2)	C3—H3A	0.9300
Co1—O5	2.130 (2)	C4—C5	1.410 (5)
Co1—O1	2.211 (3)	C4—H4A	0.9300
Co1—O6	2.309 (2)	C5—C13	1.402 (4)
O1W—H1W1	0.8199	C5—C6	1.424 (5)
O1W—H2W1	0.8201	C6—C7	1.341 (5)
O1—N3	1.229 (4)	C6—H6A	0.9300
O2—N3	1.214 (4)	C7—C8	1.426 (5)
O3—N3	1.233 (3)	C7—H7A	0.9300
O4—N4	1.225 (3)	C8—C12	1.401 (4)
O5—N4	1.253 (4)	C8—C9	1.403 (5)
O6—N4	1.247 (3)	C9—C10	1.352 (5)
N1—C2	1.335 (4)	C9—H9A	0.9300
N1—C13	1.370 (4)	C10—C11	1.411 (4)
N2—C11	1.329 (4)	C10—H10A	0.9300
N2—C12	1.370 (4)	C11—C14	1.500 (4)
C1—C2	1.485 (5)	C12—C13	1.430 (4)
C1—H1A	0.9600	C14—H14A	0.9600
C1—H1B	0.9600	C14—H14B	0.9600
C1—H1C	0.9600	C14—H14C	0.9600

O1W—Co1—N1	89.35 (8)	C3—C2—C1	120.5 (3)
O1W—Co1—N2	87.58 (9)	C4—C3—C2	120.3 (4)
N1—Co1—N2	79.24 (9)	C4—C3—H3A	119.8
O1W—Co1—O5	87.95 (10)	C2—C3—H3A	119.8
N1—Co1—O5	108.71 (10)	C3—C4—C5	120.5 (3)
N2—Co1—O5	170.84 (9)	C3—C4—H4A	119.7
O1W—Co1—O1	151.17 (10)	C5—C4—H4A	119.7
N1—Co1—O1	114.11 (10)	C13—C5—C4	116.6 (3)
N2—Co1—O1	81.06 (9)	C13—C5—C6	119.4 (3)
O5—Co1—O1	99.22 (10)	C4—C5—C6	124.0 (3)
O1W—Co1—O6	81.50 (8)	C7—C6—C5	121.0 (3)
N1—Co1—O6	163.10 (9)	C7—C6—H6A	119.5
N2—Co1—O6	114.29 (9)	C5—C6—H6A	119.5
O5—Co1—O6	57.07 (9)	C6—C7—C8	121.3 (3)
O1—Co1—O6	79.26 (10)	C6—C7—H7A	119.4
Co1—O1W—H1W1	127.3	C8—C7—H7A	119.4
Co1—O1W—H2W1	123.4	C12—C8—C9	116.6 (3)
H1W1—O1W—H2W1	107.7	C12—C8—C7	119.1 (3)
N3—O1—Co1	104.9 (2)	C9—C8—C7	124.3 (3)
N4—O5—Co1	97.33 (19)	C10—C9—C8	120.7 (3)
N4—O6—Co1	89.02 (18)	C10—C9—H9A	119.6
C2—N1—C13	118.7 (3)	C8—C9—H9A	119.6
C2—N1—Co1	128.4 (2)	C9—C10—C11	119.9 (3)
C13—N1—Co1	112.87 (19)	C9—C10—H10A	120.1
C11—N2—C12	119.1 (2)	C11—C10—H10A	120.1
C11—N2—Co1	128.28 (19)	N2—C11—C10	121.0 (3)
C12—N2—Co1	112.60 (19)	N2—C11—C14	118.3 (3)
O2—N3—O3	122.0 (3)	C10—C11—C14	120.7 (3)
O2—N3—O1	116.5 (3)	N2—C12—C8	122.6 (3)
O3—N3—O1	121.5 (3)	N2—C12—C13	117.5 (2)
O4—N4—O6	122.7 (3)	C8—C12—C13	119.8 (3)
O4—N4—O5	120.7 (3)	N1—C13—C5	122.9 (3)
O6—N4—O5	116.6 (3)	N1—C13—C12	117.7 (2)
C2—C1—H1A	109.5	C5—C13—C12	119.4 (3)
C2—C1—H1B	109.5	C11—C14—H14A	109.5
H1A—C1—H1B	109.5	C11—C14—H14B	109.5
C2—C1—H1C	109.5	H14A—C14—H14B	109.5
H1A—C1—H1C	109.5	C11—C14—H14C	109.5
H1B—C1—H1C	109.5	H14A—C14—H14C	109.5
N1—C2—C3	121.0 (3)	H14B—C14—H14C	109.5
N1—C2—C1	118.5 (3)

O1W—Co1—O1—N3	−163.77 (19)	Co1—N1—C2—C3	−179.5 (2)
N1—Co1—O1—N3	54.3 (2)	C13—N1—C2—C1	179.5 (3)
N2—Co1—O1—N3	128.2 (2)	Co1—N1—C2—C1	−0.1 (4)
O5—Co1—O1—N3	−61.1 (2)	N1—C2—C3—C4	−0.2 (5)
O6—Co1—O1—N3	−114.8 (2)	C1—C2—C3—C4	−179.6 (3)
O1W—Co1—O5—N4	80.88 (19)	C2—C3—C4—C5	0.1 (5)
N1—Co1—O5—N4	169.50 (18)	C3—C4—C5—C13	0.1 (5)
N2—Co1—O5—N4	20.0 (7)	C3—C4—C5—C6	−178.8 (3)
O1—Co1—O5—N4	−71.0 (2)	C13—C5—C6—C7	0.3 (5)
O6—Co1—O5—N4	−0.32 (17)	C4—C5—C6—C7	179.2 (3)
O1W—Co1—O6—N4	−92.77 (18)	C5—C6—C7—C8	1.1 (5)
N1—Co1—O6—N4	−34.9 (4)	C6—C7—C8—C12	−1.4 (5)
N2—Co1—O6—N4	−176.21 (16)	C6—C7—C8—C9	178.7 (3)
O5—Co1—O6—N4	0.31 (17)	C12—C8—C9—C10	0.8 (5)
O1—Co1—O6—N4	108.81 (18)	C7—C8—C9—C10	−179.3 (3)
O1W—Co1—N1—C2	91.5 (2)	C8—C9—C10—C11	−0.7 (5)
N2—Co1—N1—C2	179.2 (2)	C12—N2—C11—C10	1.0 (4)
O5—Co1—N1—C2	3.9 (3)	Co1—N2—C11—C10	−178.5 (2)
O1—Co1—N1—C2	−105.8 (2)	C12—N2—C11—C14	−178.2 (2)
O6—Co1—N1—C2	34.6 (4)	Co1—N2—C11—C14	2.3 (4)
O1W—Co1—N1—C13	−88.18 (18)	C9—C10—C11—N2	−0.3 (5)
N2—Co1—N1—C13	−0.52 (17)	C9—C10—C11—C14	178.8 (3)
O5—Co1—N1—C13	−175.80 (17)	C11—N2—C12—C8	−0.8 (4)
O1—Co1—N1—C13	74.52 (19)	Co1—N2—C12—C8	178.79 (19)
O6—Co1—N1—C13	−145.1 (3)	C11—N2—C12—C13	178.8 (2)
O1W—Co1—N2—C11	−89.6 (2)	Co1—N2—C12—C13	−1.6 (3)
N1—Co1—N2—C11	−179.4 (2)	C9—C8—C12—N2	−0.1 (4)
O5—Co1—N2—C11	−28.6 (7)	C7—C8—C12—N2	180.0 (2)
O1—Co1—N2—C11	63.9 (2)	C9—C8—C12—C13	−179.7 (3)
O6—Co1—N2—C11	−10.0 (3)	C7—C8—C12—C13	0.4 (4)
O1W—Co1—N2—C12	90.93 (17)	C2—N1—C13—C5	0.0 (4)
N1—Co1—N2—C12	1.13 (16)	Co1—N1—C13—C5	179.7 (2)
O5—Co1—N2—C12	151.8 (5)	C2—N1—C13—C12	−179.9 (2)
O1—Co1—N2—C12	−115.66 (18)	Co1—N1—C13—C12	−0.2 (3)
O6—Co1—N2—C12	170.48 (16)	C4—C5—C13—N1	−0.1 (4)
Co1—O1—N3—O2	−1.9 (3)	C6—C5—C13—N1	178.8 (3)
Co1—O1—N3—O3	179.8 (2)	C4—C5—C13—C12	179.8 (3)
Co1—O6—N4—O4	179.6 (3)	C6—C5—C13—C12	−1.3 (4)
Co1—O6—N4—O5	−0.5 (3)	N2—C12—C13—N1	1.2 (3)
Co1—O5—N4—O4	−179.5 (3)	C8—C12—C13—N1	−179.2 (2)
Co1—O5—N4—O6	0.5 (3)	N2—C12—C13—C5	−178.7 (2)
C13—N1—C2—C3	0.2 (4)	C8—C12—C13—C5	0.9 (4)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O1W—H1W1···O2ⁱ	0.82	2.49	3.096 (5)	132
O1W—H1W1···O3ⁱ	0.82	2.06	2.825 (3)	155
O1W—H2W1···O4ⁱⁱ	0.82	2.09	2.777 (4)	140
C1—H1A···O5	0.96	2.12	3.071 (4)	173
C7—H7A···O4ⁱⁱⁱ	0.93	2.54	3.418 (5)	158
C14—H14A···O6	0.96	2.38	3.333 (4)	172

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

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Aqua­(2,9-dimethyl-1,10-phenanthroline-κ2N,N′)dinitratocobalt(II)

Supporting information

Key indicators

checkCIF/PLATON results

Aqua(2,9-dimethyl-1,10-phenanthroline-κ²N,N′)dinitratocobalt(II)