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

In the title compound, [Fe(NO₃)₂(C₁₄H₁₂N₂)(H₂O)], the Fe atom is six-coordinated in an octa­hedral geometry by O and N atoms. The water mol­ecules act as donors in O—H...O hydrogen bonds, linking the mol­ecules into chains along the c axis. The chains are connected into a three-dimensional framework by other O—H...O and C—H...O hydrogen bonds. The packing is further stabilized by C—H...π and π–π inter­actions.

Key indicators

• Single-crystal X-ray study
• T = 293 K
• Mean [sigma](C-C) = 0.004 Å
• R factor = 0.038
• wR factor = 0.107
• Data-to-parameter ratio = 13.5

checkCIF/PLATON results

No syntax errors found



Alert level B
PLAT232_ALERT_2_B Hirshfeld Test Diff (M-X)  Fe1    -   O1      ..      29.24 su
PLAT232_ALERT_2_B Hirshfeld Test Diff (M-X)  Fe1    -   O4      ..      14.77 su
PLAT232_ALERT_2_B Hirshfeld Test Diff (M-X)  Fe1    -   O5      ..      29.55 su
PLAT241_ALERT_2_B Check High      Ueq as Compared to Neighbors for         O1
PLAT242_ALERT_2_B Check Low       Ueq as Compared to Neighbors for         N3

Alert level C
CRYSC01_ALERT_1_C The word below has not been recognised as a standard
            identifier.
            plate
CRYSC01_ALERT_1_C No recognised colour has been given for crystal colour.
PLAT230_ALERT_2_C Hirshfeld Test Diff for    O3     -   N3      ..       5.02 su
PLAT232_ALERT_2_C Hirshfeld Test Diff (M-X)  Fe1    -   N1      ..       6.12 su
PLAT232_ALERT_2_C Hirshfeld Test Diff (M-X)  Fe1    -   N2      ..       5.43 su
PLAT241_ALERT_2_C Check High      Ueq as Compared to Neighbors for         O4
PLAT241_ALERT_2_C Check High      Ueq as Compared to Neighbors for         O5
PLAT242_ALERT_2_C Check Low       Ueq as Compared to Neighbors for        Fe1
PLAT242_ALERT_2_C Check Low       Ueq as Compared to Neighbors for         N4
PLAT355_ALERT_3_C Long    O-H Bond (0.82A)   O1W    -   H1W    ...       1.01 Ang.
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  -FE1 -O4  -N4     20.40  0.60   1.555   1.555   1.555   1.555
PLAT710_ALERT_4_C Delete 1-2-3 or 2-3-4 Linear Torsion Angle ... #         28
            O4  -FE1 -N2  -C11   -28.70  0.60   1.555   1.555   1.555   1.555
PLAT710_ALERT_4_C Delete 1-2-3 or 2-3-4 Linear Torsion Angle ... #         33
            O4  -FE1 -N2  -C12   151.40  0.50   1.555   1.555   1.555   1.555
PLAT790_ALERT_4_C Centre of Gravity not Within Unit Cell: Resd.  #          1
              C14 H14 Fe N4 O7

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
   5 ALERT level B = Potentially serious problem
  15 ALERT level C = Check and explain
   2 ALERT level G = General alerts; check

   4 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
  12 ALERT type 2 Indicator that the structure model may be wrong or deficient
   1 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

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Computing details

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)dinitratoiron(II)

Crystal data

[Fe(NO3)2(C14H12N2)(H2O)]	F(000) = 832
Mr = 406.14	Dx = 1.618 Mg m^−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 3587 reflections
a = 11.1447 (13) Å	θ = 2.4–24.8°
b = 10.8137 (13) Å	µ = 0.95 mm^−1
c = 15.0625 (14) Å	T = 293 K
β = 113.306 (7)°	Brown, plate
V = 1667.1 (3) Å^3	0.28 × 0.19 × 0.09 mm
Z = 4

Data collection

Siemens SMART 1000 CCD area-detector diffractometer	3287 independent reflections
Radiation source: fine-focus sealed tube	2747 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.024
Detector resolution: 8.33 pixels mm^-1	θmax = 26.1°, θmin = 2.0°
ω scans	h = −13→11
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	k = −12→13
Tmin = 0.777, Tmax = 0.919	l = −17→18
9395 measured reflections

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)] = 0.038	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.107	H atoms treated by a mixture of independent and constrained refinement
S = 1.04	w = 1/[σ^2(Fo^2) + (0.0646P)^2 + 0.2884P] where P = (Fo^2 + 2Fc^2)/3
3287 reflections	(Δ/σ)max < 0.001
243 parameters	Δρmax = 0.32 e Å^−3
0 restraints	Δρmin = −0.37 e Å^−3

Special details

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 (Ų)

	x	y	z	Uiso*/Ueq
Fe1	0.18586 (3)	−0.21765 (3)	−0.03978 (2)	0.04389 (14)
O1W	0.1224 (2)	−0.2240 (2)	0.07252 (16)	0.0665 (5)
O1	0.2888 (2)	−0.1243 (3)	−0.12013 (14)	0.1000 (8)
O2	0.1746 (3)	−0.2632 (2)	−0.2104 (2)	0.1128 (10)
O3	0.29007 (19)	−0.1477 (2)	−0.26142 (13)	0.0713 (5)
O4	−0.0109 (2)	−0.1784 (2)	−0.13457 (15)	0.0790 (6)
O5	0.09589 (19)	−0.0221 (2)	−0.05798 (14)	0.0737 (5)
O6	−0.1064 (2)	−0.0010 (2)	−0.15652 (15)	0.0917 (7)
N1	0.21161 (19)	−0.41168 (19)	−0.02963 (13)	0.0505 (5)
N2	0.38016 (19)	−0.23061 (18)	0.06581 (13)	0.0471 (4)
N3	0.2513 (2)	−0.1776 (2)	−0.19803 (16)	0.0620 (6)
N4	−0.0092 (2)	−0.0650 (2)	−0.11710 (15)	0.0622 (6)
C1	−0.0064 (3)	−0.4612 (3)	−0.1472 (2)	0.0834 (9)
H1A	−0.0123	−0.3726	−0.1488	0.125*
H1B	−0.0718	−0.4948	−0.1275	0.125*
H1C	−0.0200	−0.4916	−0.2103	0.125*
C2	0.1257 (3)	−0.4994 (3)	−0.0769 (2)	0.0621 (6)
C3	0.1592 (3)	−0.6256 (3)	−0.0607 (3)	0.0808 (9)
H3A	0.0984	−0.6856	−0.0942	0.097*
C4	0.2786 (3)	−0.6602 (3)	0.0030 (3)	0.0802 (9)
H4A	0.2999	−0.7436	0.0130	0.096*
C5	0.3708 (3)	−0.5697 (2)	0.0542 (2)	0.0614 (6)
C6	0.5002 (3)	−0.5978 (3)	0.1212 (2)	0.0738 (8)
H6A	0.5260	−0.6799	0.1335	0.089*
C7	0.5852 (3)	−0.5077 (3)	0.1667 (2)	0.0713 (8)
H7A	0.6694	−0.5285	0.2090	0.086*
C8	0.5482 (2)	−0.3802 (3)	0.15102 (17)	0.0577 (6)
C9	0.6312 (3)	−0.2818 (3)	0.1978 (2)	0.0704 (8)
H9A	0.7159	−0.2977	0.2419	0.085*
C10	0.5882 (3)	−0.1636 (3)	0.17887 (19)	0.0685 (7)
H10A	0.6435	−0.0987	0.2101	0.082*
C11	0.4603 (2)	−0.1385 (2)	0.11229 (16)	0.0548 (6)
C12	0.4223 (2)	−0.3495 (2)	0.08496 (15)	0.0485 (5)
C13	0.3322 (2)	−0.4459 (2)	0.03532 (16)	0.0503 (6)
C14	0.4097 (3)	−0.0095 (3)	0.09242 (19)	0.0665 (7)
H14A	0.3216	−0.0105	0.0449	0.100*
H14B	0.4635	0.0379	0.0686	0.100*
H14C	0.4116	0.0271	0.1510	0.100*
H2W	0.106 (4)	−0.160 (5)	0.097 (3)	0.138 (17)*
H1W	0.193 (4)	−0.259 (4)	0.133 (3)	0.120 (15)*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
Fe1	0.0381 (2)	0.0428 (2)	0.0465 (2)	0.00529 (12)	0.01216 (14)	0.00253 (13)
O1W	0.0705 (13)	0.0685 (13)	0.0679 (12)	0.0108 (10)	0.0354 (10)	0.0050 (10)
O1	0.0888 (15)	0.159 (3)	0.0487 (11)	0.0095 (16)	0.0233 (10)	−0.0095 (13)
O2	0.135 (2)	0.0828 (17)	0.153 (3)	−0.0114 (16)	0.091 (2)	0.0156 (16)
O3	0.0768 (12)	0.0907 (15)	0.0556 (10)	−0.0085 (11)	0.0359 (9)	−0.0005 (10)
O4	0.0672 (12)	0.0735 (13)	0.0776 (13)	0.0192 (10)	0.0087 (10)	−0.0115 (11)
O5	0.0641 (12)	0.0769 (13)	0.0686 (12)	0.0028 (10)	0.0137 (10)	0.0057 (10)
O6	0.0738 (13)	0.0987 (16)	0.0776 (13)	0.0471 (13)	0.0034 (10)	0.0010 (12)
N1	0.0519 (11)	0.0484 (11)	0.0543 (11)	0.0011 (9)	0.0242 (9)	0.0025 (9)
N2	0.0446 (11)	0.0523 (11)	0.0434 (10)	0.0063 (8)	0.0163 (9)	0.0026 (8)
N3	0.0638 (13)	0.0684 (14)	0.0572 (13)	0.0226 (12)	0.0275 (11)	0.0147 (11)
N4	0.0553 (13)	0.0703 (15)	0.0538 (12)	0.0184 (11)	0.0139 (10)	0.0012 (11)
C1	0.0635 (18)	0.074 (2)	0.098 (2)	−0.0196 (15)	0.0167 (16)	−0.0127 (17)
C2	0.0603 (15)	0.0547 (15)	0.0758 (17)	−0.0080 (12)	0.0318 (13)	−0.0033 (13)
C3	0.088 (2)	0.0537 (17)	0.110 (2)	−0.0110 (15)	0.0486 (19)	−0.0081 (17)
C4	0.096 (2)	0.0469 (16)	0.114 (2)	0.0086 (15)	0.058 (2)	0.0081 (16)
C5	0.0764 (17)	0.0526 (15)	0.0673 (15)	0.0122 (13)	0.0415 (14)	0.0097 (12)
C6	0.082 (2)	0.0655 (18)	0.0815 (19)	0.0349 (16)	0.0405 (16)	0.0246 (15)
C7	0.0669 (17)	0.085 (2)	0.0629 (16)	0.0332 (16)	0.0268 (14)	0.0197 (15)
C8	0.0519 (14)	0.0748 (17)	0.0472 (12)	0.0185 (12)	0.0204 (11)	0.0097 (12)
C9	0.0494 (15)	0.096 (2)	0.0539 (15)	0.0131 (14)	0.0074 (12)	0.0013 (14)
C10	0.0510 (14)	0.085 (2)	0.0580 (15)	0.0003 (14)	0.0089 (12)	−0.0079 (14)
C11	0.0502 (13)	0.0648 (16)	0.0455 (12)	0.0011 (11)	0.0149 (10)	−0.0036 (11)
C12	0.0493 (13)	0.0566 (14)	0.0443 (11)	0.0113 (11)	0.0235 (10)	0.0070 (10)
C13	0.0560 (14)	0.0526 (13)	0.0495 (12)	0.0114 (11)	0.0287 (11)	0.0090 (10)
C14	0.0673 (17)	0.0579 (15)	0.0656 (16)	−0.0058 (13)	0.0171 (13)	−0.0092 (13)

Geometric parameters (Å, º)

Fe1—O1W	2.077 (2)	C2—C3	1.411 (4)
Fe1—N1	2.115 (2)	C3—C4	1.349 (5)
Fe1—N2	2.1244 (19)	C3—H3A	0.9300
Fe1—O4	2.133 (2)	C4—C5	1.408 (4)
Fe1—O1	2.213 (2)	C4—H4A	0.9300
Fe1—O5	2.310 (2)	C5—C13	1.400 (3)
O1W—H2W	0.84 (5)	C5—C6	1.428 (4)
O1W—H1W	1.02 (4)	C6—C7	1.342 (5)
O1—N3	1.223 (3)	C6—H6A	0.9300
O2—N3	1.223 (3)	C7—C8	1.432 (4)
O3—N3	1.237 (3)	C7—H7A	0.9300
O4—N4	1.252 (3)	C8—C12	1.401 (3)
O5—N4	1.247 (3)	C8—C9	1.403 (4)
O6—N4	1.223 (3)	C9—C10	1.355 (4)
N1—C2	1.335 (3)	C9—H9A	0.9300
N1—C13	1.364 (3)	C10—C11	1.407 (3)
N2—C11	1.336 (3)	C10—H10A	0.9300
N2—C12	1.360 (3)	C11—C14	1.489 (4)
C1—C2	1.492 (4)	C12—C13	1.435 (3)
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—Fe1—N1	89.33 (8)	C3—C2—C1	120.7 (3)
O1W—Fe1—N2	87.87 (8)	C4—C3—C2	120.7 (3)
N1—Fe1—N2	79.13 (8)	C4—C3—H3A	119.7
O1W—Fe1—O4	87.73 (9)	C2—C3—H3A	119.7
N1—Fe1—O4	108.66 (8)	C3—C4—C5	119.9 (3)
N2—Fe1—O4	171.00 (8)	C3—C4—H4A	120.1
O1W—Fe1—O1	151.39 (9)	C5—C4—H4A	120.1
N1—Fe1—O1	114.01 (9)	C13—C5—C4	117.0 (3)
N2—Fe1—O1	81.03 (8)	C13—C5—C6	119.3 (3)
O4—Fe1—O1	99.29 (9)	C4—C5—C6	123.6 (3)
O1W—Fe1—O5	81.69 (8)	C7—C6—C5	121.2 (3)
N1—Fe1—O5	163.13 (7)	C7—C6—H6A	119.4
N2—Fe1—O5	114.54 (7)	C5—C6—H6A	119.4
O4—Fe1—O5	56.99 (8)	C6—C7—C8	121.0 (3)
O1—Fe1—O5	79.18 (9)	C6—C7—H7A	119.5
Fe1—O1W—H2W	123 (3)	C8—C7—H7A	119.5
Fe1—O1W—H1W	111 (2)	C12—C8—C9	116.9 (2)
H2W—O1W—H1W	97 (4)	C12—C8—C7	119.2 (3)
N3—O1—Fe1	104.8 (2)	C9—C8—C7	123.9 (2)
N4—O4—Fe1	97.34 (16)	C10—C9—C8	120.1 (3)
N4—O5—Fe1	89.11 (15)	C10—C9—H9A	120.0
C2—N1—C13	119.0 (2)	C8—C9—H9A	120.0
C2—N1—Fe1	128.17 (17)	C9—C10—C11	120.5 (3)
C13—N1—Fe1	112.81 (16)	C9—C10—H10A	119.8
C11—N2—C12	119.4 (2)	C11—C10—H10A	119.8
C11—N2—Fe1	127.95 (16)	N2—C11—C10	120.5 (2)
C12—N2—Fe1	112.68 (16)	N2—C11—C14	118.2 (2)
O1—N3—O2	117.1 (3)	C10—C11—C14	121.3 (2)
O1—N3—O3	121.7 (3)	N2—C12—C8	122.6 (2)
O2—N3—O3	121.1 (3)	N2—C12—C13	117.66 (19)
O6—N4—O5	122.5 (3)	C8—C12—C13	119.7 (2)
O6—N4—O4	121.0 (2)	N1—C13—C5	122.8 (2)
O5—N4—O4	116.6 (2)	N1—C13—C12	117.7 (2)
C2—C1—H1A	109.5	C5—C13—C12	119.5 (2)
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	120.7 (3)	H14B—C14—H14C	109.5
N1—C2—C1	118.7 (3)
O1W—Fe1—O1—N3	−163.61 (17)	Fe1—N1—C2—C3	−179.52 (19)
N1—Fe1—O1—N3	54.20 (19)	C13—N1—C2—C1	179.5 (2)
N2—Fe1—O1—N3	127.98 (19)	Fe1—N1—C2—C1	0.5 (4)
O4—Fe1—O1—N3	−61.13 (19)	N1—C2—C3—C4	0.1 (4)
O5—Fe1—O1—N3	−114.75 (18)	C1—C2—C3—C4	−179.9 (3)
O1W—Fe1—O4—N4	81.21 (17)	C2—C3—C4—C5	0.3 (5)
N1—Fe1—O4—N4	169.74 (15)	C3—C4—C5—C13	−0.2 (4)
N2—Fe1—O4—N4	20.4 (6)	C3—C4—C5—C6	−178.5 (3)
O1—Fe1—O4—N4	−70.89 (18)	C13—C5—C6—C7	0.3 (4)
O5—Fe1—O4—N4	−0.35 (14)	C4—C5—C6—C7	178.6 (3)
O1W—Fe1—O5—N4	−92.35 (15)	C5—C6—C7—C8	1.3 (4)
N1—Fe1—O5—N4	−33.8 (3)	C6—C7—C8—C12	−1.9 (4)
N2—Fe1—O5—N4	−176.15 (14)	C6—C7—C8—C9	178.5 (3)
O4—Fe1—O5—N4	0.35 (14)	C12—C8—C9—C10	0.5 (4)
O1—Fe1—O5—N4	109.02 (15)	C7—C8—C9—C10	−179.9 (3)
O1W—Fe1—N1—C2	91.0 (2)	C8—C9—C10—C11	0.0 (4)
N2—Fe1—N1—C2	179.0 (2)	C12—N2—C11—C10	1.4 (3)
O4—Fe1—N1—C2	3.7 (2)	Fe1—N2—C11—C10	−178.39 (17)
O1—Fe1—N1—C2	−106.0 (2)	C12—N2—C11—C14	−177.8 (2)
O5—Fe1—N1—C2	33.5 (4)	Fe1—N2—C11—C14	2.3 (3)
O1W—Fe1—N1—C13	−88.01 (16)	C9—C10—C11—N2	−1.0 (4)
N2—Fe1—N1—C13	−0.05 (14)	C9—C10—C11—C14	178.3 (3)
O4—Fe1—N1—C13	−175.39 (14)	C11—N2—C12—C8	−1.0 (3)
O1—Fe1—N1—C13	74.92 (16)	Fe1—N2—C12—C8	178.89 (16)
O5—Fe1—N1—C13	−145.5 (2)	C11—N2—C12—C13	178.5 (2)
O1W—Fe1—N2—C11	−89.5 (2)	Fe1—N2—C12—C13	−1.7 (2)
N1—Fe1—N2—C11	−179.2 (2)	C9—C8—C12—N2	0.0 (3)
O4—Fe1—N2—C11	−28.7 (6)	C7—C8—C12—N2	−179.7 (2)
O1—Fe1—N2—C11	64.0 (2)	C9—C8—C12—C13	−179.4 (2)
O5—Fe1—N2—C11	−9.7 (2)	C7—C8—C12—C13	0.9 (3)
O1W—Fe1—N2—C12	90.66 (15)	C2—N1—C13—C5	0.6 (3)
N1—Fe1—N2—C12	0.93 (14)	Fe1—N1—C13—C5	179.76 (18)
O4—Fe1—N2—C12	151.4 (5)	C2—N1—C13—C12	−180.0 (2)
O1—Fe1—N2—C12	−115.80 (16)	Fe1—N1—C13—C12	−0.8 (2)
O5—Fe1—N2—C12	170.52 (14)	C4—C5—C13—N1	−0.3 (4)
Fe1—O1—N3—O2	−1.2 (3)	C6—C5—C13—N1	178.2 (2)
Fe1—O1—N3—O3	179.74 (19)	C4—C5—C13—C12	−179.7 (2)
Fe1—O5—N4—O6	179.4 (2)	C6—C5—C13—C12	−1.2 (4)
Fe1—O5—N4—O4	−0.6 (2)	N2—C12—C13—N1	1.7 (3)
Fe1—O4—N4—O6	−179.3 (2)	C8—C12—C13—N1	−178.82 (19)
Fe1—O4—N4—O5	0.6 (3)	N2—C12—C13—C5	−178.8 (2)
C13—N1—C2—C3	−0.5 (4)	C8—C12—C13—C5	0.6 (3)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
O1W—H1W···O2^i	1.01 (4)	2.46 (4)	3.089 (4)	120 (3)
O1W—H1W···O3^i	1.01 (4)	1.83 (4)	2.824 (3)	166 (4)
O1W—H2W···O6^ii	0.84 (5)	1.96 (5)	2.780 (3)	167 (5)
C7—H7A···O6^iii	0.93	2.54	3.416 (4)	158

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