Ethyl­ene­diammonium dichloride bis­(1,10-phen­anthroline) tetra­hydrate

The title compound, C₂H₁₀N₂²⁺·2Cl⁻·2C₁₂H₈N₂·4H₂O, has an inversion centre located midway between the two C atoms of the ethyl­ene­diammonium cation. The 1,10-phenanthroline mol­ecules stack along the a axis, and are linked by π–π stacking inter­actions to form one-dimensional chains. These are bridged by ethyl­ene­diammonium cations, via hydrogen bonds, forming two-dimensional supra­molecular sheets parallel to the ac plane. Hydrogen bonds to chloride anions and water mol­ecules connect these two-dimensional sheets, resulting in the formation of a three-dimensional supra­molecular network.

Key indicators

• Single-crystal X-ray study
• T = 291 K
• Mean [sigma](C-C) = 0.003 Å
• R factor = 0.036
• wR factor = 0.103
• Data-to-parameter ratio = 12.7

checkCIF/PLATON results

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Alert level C
PLAT029_ALERT_3_C _diffrn_measured_fraction_theta_full Low .......       0.96

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

   0 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
   0 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
   0 ALERT type 4 Improvement, methodology, query or suggestion

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Computing details

Data collection: SMART (Bruker, 1998); cell refinement: SMART; data reduction: SAINT (Bruker, 1998); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: SHELXTL (Bruker, 1997); software used to prepare material for publication: SHELXTL.

Ethylenediammonium dichloride bis(1,10-phenanthroline) tetrahydrate

Crystal data

C2H10N2^2+·2Cl^−·2C12H8N2·4H2O	Z = 2
Mr = 282.75	F(000) = 298
Triclinic, P1	Dx = 1.321 Mg m^−3
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 7.6518 (8) Å	Cell parameters from 1423 reflections
b = 9.8985 (10) Å	θ = 2.5–26.2°
c = 10.6525 (11) Å	µ = 0.27 mm^−1
α = 69.492 (2)°	T = 291 K
β = 70.416 (2)°	Block, yellow
γ = 80.602 (2)°	0.35 × 0.30 × 0.12 mm
V = 711.02 (13) Å^3

Data collection

Bruker SMART CCD area-detector diffractometer	2402 independent reflections
Radiation source: fine-focus sealed tube	2013 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.014
φ and ω scans	θmax = 25.0°, θmin = 2.5°
Absorption correction: multi-scan (SADABS; Bruker, 1998)	h = −9→7
Tmin = 0.912, Tmax = 0.967	k = −11→11
3211 measured reflections	l = −12→12

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)] = 0.036	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.103	H atoms treated by a mixture of independent and constrained refinement
S = 1.07	w = 1/[σ^2(Fo^2) + (0.049P)^2 + 0.1558P] where P = (Fo^2 + 2Fc^2)/3
2402 reflections	(Δ/σ)max < 0.001
189 parameters	Δρmax = 0.15 e Å^−3
6 restraints	Δρmin = −0.17 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
Cl1	0.26183 (7)	0.81920 (5)	0.42322 (6)	0.0703 (2)
O1	0.3051 (2)	0.25192 (17)	0.64136 (18)	0.0719 (4)
O2	0.8352 (3)	0.9093 (2)	0.4578 (3)	0.1015 (6)
N1	0.1339 (2)	0.66044 (16)	1.07722 (16)	0.0538 (4)
N2	0.1341 (2)	0.36811 (16)	1.14794 (15)	0.0500 (4)
N3	0.09620 (19)	0.51495 (16)	0.63567 (14)	0.0488 (4)
H3A	0.1706	0.4353	0.6442	0.073*
H3B	0.0399	0.5250	0.7200	0.073*
H3C	0.1630	0.5913	0.5802	0.073*
C1	0.1349 (3)	0.8029 (2)	1.0401 (2)	0.0679 (6)
H1	0.0647	0.8474	1.1062	0.081*
C2	0.2340 (3)	0.8901 (2)	0.9088 (3)	0.0731 (6)
H2	0.2282	0.9899	0.8880	0.088*
C3	0.3391 (3)	0.8272 (2)	0.8119 (2)	0.0650 (5)
H3	0.4066	0.8837	0.7235	0.078*
C4	0.3461 (2)	0.6764 (2)	0.84501 (18)	0.0500 (4)
C5	0.4558 (3)	0.6013 (2)	0.74925 (19)	0.0581 (5)
H5	0.5245	0.6539	0.6595	0.070*
C6	0.4617 (2)	0.4572 (2)	0.78595 (19)	0.0575 (5)
H6	0.5352	0.4113	0.7219	0.069*
C7	0.3563 (2)	0.3728 (2)	0.92244 (18)	0.0487 (4)
C8	0.3612 (3)	0.2214 (2)	0.9657 (2)	0.0620 (5)
H8	0.4361	0.1717	0.9055	0.074*
C9	0.2552 (3)	0.1482 (2)	1.0963 (2)	0.0697 (6)
H9	0.2581	0.0478	1.1272	0.084*
C10	0.1423 (3)	0.2258 (2)	1.1832 (2)	0.0634 (5)
H10	0.0682	0.1744	1.2714	0.076*
C11	0.2424 (2)	0.44222 (18)	1.01870 (16)	0.0420 (4)
C12	0.2392 (2)	0.59737 (18)	0.98017 (17)	0.0433 (4)
C13	−0.0447 (2)	0.5038 (2)	0.57350 (17)	0.0471 (4)
H13A	−0.1317	0.5870	0.5712	0.057*
H13B	−0.1134	0.4179	0.6316	0.057*
H1W	0.4215 (15)	0.234 (3)	0.630 (3)	0.102 (9)*
H2W	0.264 (3)	0.197 (2)	0.613 (3)	0.090 (8)*
H3W	0.9526 (15)	0.892 (3)	0.435 (3)	0.110 (10)*
H4W	0.799 (4)	0.983 (3)	0.485 (4)	0.153 (15)*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
Cl1	0.0569 (3)	0.0568 (3)	0.0902 (4)	0.0004 (2)	−0.0138 (3)	−0.0245 (3)
O1	0.0605 (10)	0.0753 (10)	0.0964 (12)	0.0104 (8)	−0.0317 (8)	−0.0454 (9)
O2	0.0852 (14)	0.0955 (14)	0.167 (2)	0.0148 (10)	−0.0650 (14)	−0.0762 (14)
N1	0.0558 (9)	0.0524 (9)	0.0490 (9)	0.0035 (7)	−0.0111 (7)	−0.0186 (7)
N2	0.0565 (9)	0.0515 (9)	0.0405 (8)	−0.0072 (7)	−0.0109 (7)	−0.0143 (7)
N3	0.0449 (8)	0.0606 (9)	0.0407 (8)	−0.0043 (6)	−0.0075 (6)	−0.0202 (7)
C1	0.0758 (14)	0.0539 (12)	0.0705 (14)	0.0091 (10)	−0.0178 (11)	−0.0252 (10)
C2	0.0826 (15)	0.0478 (11)	0.0816 (16)	−0.0007 (10)	−0.0267 (13)	−0.0111 (11)
C3	0.0645 (13)	0.0606 (12)	0.0575 (12)	−0.0122 (10)	−0.0182 (10)	−0.0002 (10)
C4	0.0440 (9)	0.0604 (11)	0.0421 (10)	−0.0065 (8)	−0.0141 (7)	−0.0094 (8)
C5	0.0466 (10)	0.0816 (14)	0.0394 (10)	−0.0112 (9)	−0.0056 (8)	−0.0147 (9)
C6	0.0452 (10)	0.0826 (14)	0.0477 (11)	−0.0036 (9)	−0.0056 (8)	−0.0319 (10)
C7	0.0448 (9)	0.0613 (11)	0.0479 (10)	−0.0002 (8)	−0.0169 (8)	−0.0251 (8)
C8	0.0666 (12)	0.0636 (12)	0.0670 (13)	0.0061 (10)	−0.0218 (10)	−0.0365 (11)
C9	0.0932 (16)	0.0498 (11)	0.0721 (15)	−0.0018 (11)	−0.0299 (12)	−0.0224 (10)
C10	0.0825 (14)	0.0543 (12)	0.0506 (11)	−0.0141 (10)	−0.0177 (10)	−0.0108 (9)
C11	0.0397 (8)	0.0516 (10)	0.0372 (9)	−0.0019 (7)	−0.0136 (7)	−0.0154 (7)
C12	0.0396 (9)	0.0523 (10)	0.0392 (9)	−0.0001 (7)	−0.0139 (7)	−0.0152 (8)
C13	0.0371 (8)	0.0603 (10)	0.0421 (9)	−0.0026 (7)	−0.0054 (7)	−0.0203 (8)

Geometric parameters (Å, º)

O1—H1W	0.854 (10)	C4—C12	1.408 (2)
O1—H2W	0.849 (10)	C4—C5	1.432 (3)
O2—H3W	0.853 (10)	C5—C6	1.338 (3)
O2—H4W	0.85 (3)	C5—H5	0.9300
N1—C1	1.325 (2)	C6—C7	1.430 (3)
N1—C12	1.356 (2)	C6—H6	0.9300
N2—C10	1.321 (2)	C7—C8	1.403 (3)
N2—C11	1.359 (2)	C7—C11	1.408 (2)
N3—C13	1.477 (2)	C8—C9	1.360 (3)
N3—H3A	0.8900	C8—H8	0.9300
N3—H3B	0.8900	C9—C10	1.393 (3)
N3—H3C	0.8900	C9—H9	0.9300
C1—C2	1.391 (3)	C10—H10	0.9300
C1—H1	0.9300	C11—C12	1.442 (2)
C2—C3	1.353 (3)	C13—C13^i	1.507 (3)
C2—H2	0.9300	C13—H13A	0.9700
C3—C4	1.405 (3)	C13—H13B	0.9700
C3—H3	0.9300
H1W—O1—H2W	110.3 (19)	C5—C6—H6	119.6
H3W—O2—H4W	114 (2)	C7—C6—H6	119.6
C1—N1—C12	116.98 (17)	C8—C7—C11	117.81 (17)
C10—N2—C11	117.56 (16)	C8—C7—C6	122.54 (17)
C13—N3—H3A	109.5	C11—C7—C6	119.65 (17)
C13—N3—H3B	109.5	C9—C8—C7	119.38 (18)
H3A—N3—H3B	109.5	C9—C8—H8	120.3
C13—N3—H3C	109.5	C7—C8—H8	120.3
H3A—N3—H3C	109.5	C8—C9—C10	118.98 (19)
H3B—N3—H3C	109.5	C8—C9—H9	120.5
N1—C1—C2	124.3 (2)	C10—C9—H9	120.5
N1—C1—H1	117.9	N2—C10—C9	123.93 (19)
C2—C1—H1	117.9	N2—C10—H10	118.0
C3—C2—C1	118.8 (2)	C9—C10—H10	118.0
C3—C2—H2	120.6	N2—C11—C7	122.29 (16)
C1—C2—H2	120.6	N2—C11—C12	118.24 (15)
C2—C3—C4	119.88 (19)	C7—C11—C12	119.46 (15)
C2—C3—H3	120.1	N1—C12—C4	122.95 (16)
C4—C3—H3	120.1	N1—C12—C11	118.02 (15)
C3—C4—C12	117.16 (18)	C4—C12—C11	119.03 (15)
C3—C4—C5	123.35 (17)	N3—C13—C13^i	111.10 (16)
C12—C4—C5	119.49 (17)	N3—C13—H13A	109.4
C6—C5—C4	121.48 (17)	C13^i—C13—H13A	109.4
C6—C5—H5	119.3	N3—C13—H13B	109.4
C4—C5—H5	119.3	C13^i—C13—H13B	109.4
C5—C6—C7	120.84 (17)	H13A—C13—H13B	108.0
C12—N1—C1—C2	1.0 (3)	C10—N2—C11—C12	−178.20 (15)
N1—C1—C2—C3	−0.9 (4)	C8—C7—C11—N2	−2.4 (2)
C1—C2—C3—C4	0.1 (3)	C6—C7—C11—N2	177.57 (15)
C2—C3—C4—C12	0.6 (3)	C8—C7—C11—C12	177.60 (15)
C2—C3—C4—C5	−179.10 (19)	C6—C7—C11—C12	−2.4 (2)
C3—C4—C5—C6	178.58 (18)	C1—N1—C12—C4	−0.2 (3)
C12—C4—C5—C6	−1.1 (3)	C1—N1—C12—C11	179.19 (16)
C4—C5—C6—C7	0.7 (3)	C3—C4—C12—N1	−0.6 (3)
C5—C6—C7—C8	−178.90 (17)	C5—C4—C12—N1	179.12 (16)
C5—C6—C7—C11	1.1 (3)	C3—C4—C12—C11	−179.94 (15)
C11—C7—C8—C9	1.0 (3)	C5—C4—C12—C11	−0.2 (2)
C6—C7—C8—C9	−179.04 (18)	N2—C11—C12—N1	2.6 (2)
C7—C8—C9—C10	0.9 (3)	C7—C11—C12—N1	−177.42 (15)
C11—N2—C10—C9	0.2 (3)	N2—C11—C12—C4	−178.02 (15)
C8—C9—C10—N2	−1.6 (3)	C7—C11—C12—C4	2.0 (2)
C10—N2—C11—C7	1.8 (2)

Symmetry code: (i) −x, −y+1, −z+1.

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
N3—H3A···O1	0.89	1.94	2.816 (2)	168
N3—H3B···N2^ii	0.89	2.05	2.870 (2)	153
N3—H3B···N1^ii	0.89	2.43	3.023 (2)	125
N3—H3C···Cl1	0.89	2.35	3.2165 (16)	164
O1—H1W···Cl1^iii	0.85 (1)	2.31 (1)	3.1623 (16)	174 (2)
O1—H2W···O2^iii	0.85 (1)	1.86 (1)	2.705 (2)	176 (2)
O2—H3W···Cl1^iv	0.85 (1)	2.33 (1)	3.172 (2)	168 (3)
O2—H4W···Cl1^v	0.85 (3)	2.40 (3)	3.238 (2)	171 (3)

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