Aqua­[N¹-(2-oxidobenzyl­ideneamino)-3-aza­pentane-1,5-diamine]iron(II) chloride

The title compound, [Fe(C₁₁H₁₈N₃O₂)(H₂O)]Cl, is a mononuclear iron(II) complex, consisting of one coordination cation and one uncoordinated Cl^- anion. The central metal has distorted square-pyramidal geometry. Weak inter­molecular hydrogen bonds link the mol­ecules to form two-dimensional layers parallel to the bc plane.

Key indicators

• Single-crystal X-ray study
• T = 293 K
• Mean [sigma](C-C) = 0.007 Å
• R factor = 0.045
• wR factor = 0.122
• Data-to-parameter ratio = 14.1

checkCIF/PLATON results

No syntax errors found



Alert level C
PLAT062_ALERT_4_C Rescale T(min) & T(max) by .....................       0.79
PLAT125_ALERT_4_C No _symmetry_space_group_name_Hall Given .......          ?
PLAT232_ALERT_2_C Hirshfeld Test Diff (M-X)  Fe1    -   O1      ..       7.09 su
PLAT232_ALERT_2_C Hirshfeld Test Diff (M-X)  Fe1    -   O1W     ..       6.81 su
PLAT232_ALERT_2_C Hirshfeld Test Diff (M-X)  Fe1    -   N1      ..       7.96 su
PLAT232_ALERT_2_C Hirshfeld Test Diff (M-X)  Fe1    -   N2      ..       7.25 su
PLAT232_ALERT_2_C Hirshfeld Test Diff (M-X)  Fe1    -   N3      ..       9.84 su
PLAT241_ALERT_2_C Check High      Ueq as Compared to Neighbors for         O1
PLAT242_ALERT_2_C Check Low       Ueq as Compared to Neighbors for        Fe1
PLAT341_ALERT_3_C Low Bond Precision on C-C bonds (x 1000) Ang ...          7
PLAT710_ALERT_4_C Delete 1-2-3 or 2-3-4 Linear Torsion Angle ... #          2
            N2  -FE1 -O1  -C1    -68.70  1.60   1.555   1.555   1.555   1.555
PLAT710_ALERT_4_C Delete 1-2-3 or 2-3-4 Linear Torsion Angle ... #         13
            O1  -FE1 -N2  -C10   -72.70  1.50   1.555   1.555   1.555   1.555
PLAT710_ALERT_4_C Delete 1-2-3 or 2-3-4 Linear Torsion Angle ... #         17
            O1  -FE1 -N2  -C9     53.90  1.60   1.555   1.555   1.555   1.555
PLAT720_ALERT_4_C Number of Unusual/Non-Standard Label(s) ........          4
PLAT735_ALERT_1_C D-H     Calc     0.84(3), Rep   0.843(10) ......       3.00 su-Ra
              O1W  -H3#     1.555   1.555
PLAT736_ALERT_1_C H...A   Calc     1.84(3), Rep   1.842(14) ......       2.14 su-Ra
              H3#  -O1      1.555   3.565

Alert level G
ABSTM02_ALERT_3_G  When printed, the submitted absorption T values will be
            replaced by the scaled T values. Since the ratio of scaled T's
            is identical to the ratio of reported T values, the scaling
            does not imply a change to the absorption corrections used in
            the study.
            Ratio of Tmax expected/reported      0.794
            Tmax scaled      0.582 Tmin scaled      0.495
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
   0 ALERT level B = Potentially serious problem
  16 ALERT level C = Check and explain
   3 ALERT level G = General alerts; check

   4 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
   7 ALERT type 2 Indicator that the structure model may be wrong or deficient
   2 ALERT type 3 Indicator that the structure quality may be low
   6 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: SMART; data reduction: SAINT (Siemens, 1996); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: SHELXTL (Sheldrick, 1997); software used to prepare material for publication: SHELXTL.

Aqua[N¹-(2-oxidobenzylideneamino)-3-azapentane-1,5-diamine]iron(II) chloride

Crystal data

[Fe(C11H18N3O2)(H2O)]Cl	F(000) = 656
Mr = 315.58	Dx = 1.601 Mg m^−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
a = 9.059 (4) Å	Cell parameters from 550 reflections
b = 13.679 (5) Å	θ = 7.3–26.2°
c = 10.800 (5) Å	µ = 1.35 mm^−1
β = 101.88 (1)°	T = 293 K
V = 1309.6 (10) Å^3	Prism, green
Z = 4	0.5 × 0.4 × 0.4 mm

Data collection

Bruker SMART CCD area-detector diffractometer	2425 independent reflections
Radiation source: fine-focus sealed tube	2055 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.026
φ and ω scans	θmax = 25.5°, θmin = 2.3°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = 0→10
Tmin = 0.623, Tmax = 0.733	k = 0→16
2581 measured reflections	l = −13→12

Refinement

Refinement on F^2	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F^2 > 2σ(F^2)] = 0.045	H atoms treated by a mixture of independent and constrained refinement
wR(F^2) = 0.122	w = 1/[σ^2(Fo^2) + (0.044P)^2 + 3.4826P] where P = (Fo^2 + 2Fc^2)/3
S = 1.08	(Δ/σ)max < 0.001
2425 reflections	Δρmax = 0.56 e Å^−3
172 parameters	Δρmin = −0.52 e Å^−3
3 restraints	Extinction correction: SHELXL97 (Sheldrick, 1997), Fc^*=kFc[1+0.001xFc^2λ^3/sin(2θ)]^-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.0127 (18)

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	0.17061 (6)	0.41927 (4)	0.16061 (5)	0.0294 (2)
Cl1	0.19816 (16)	0.66842 (10)	0.40226 (12)	0.0595 (4)
O1W	0.1386 (4)	0.5851 (3)	0.1271 (3)	0.0490 (8)
O1	0.1512 (3)	0.3912 (3)	−0.0149 (3)	0.0534 (9)
N1	0.3874 (4)	0.4151 (3)	0.1925 (3)	0.0430 (8)
N2	0.1972 (5)	0.4345 (3)	0.3481 (3)	0.0473 (9)
H2N	0.1843	0.4987	0.3630	0.050*
N3	−0.0452 (4)	0.3892 (3)	0.1652 (3)	0.0486 (9)
H3NA	−0.0696	0.3211	0.1385	0.050*
H3NB	−0.0992	0.4283	0.1022	0.050*
C1	0.2601 (5)	0.3709 (3)	−0.0761 (4)	0.0392 (9)
C2	0.2202 (5)	0.3470 (3)	−0.2048 (4)	0.0450 (10)
H2A	0.1151	0.3462	−0.2450	0.080*
C3	0.3257 (6)	0.3240 (3)	−0.2731 (4)	0.0511 (12)
H3A	0.2945	0.3076	−0.3615	0.080*
C4	0.4780 (6)	0.3247 (4)	−0.2173 (5)	0.0560 (13)
H4A	0.5529	0.3077	−0.2652	0.080*
C5	0.5199 (6)	0.3487 (4)	−0.0907 (5)	0.0515 (12)
H5A	0.6252	0.3502	−0.0511	0.080*
C6	0.4134 (5)	0.3717 (3)	−0.0182 (4)	0.0406 (10)
C7	0.4690 (5)	0.3940 (3)	0.1134 (4)	0.0460 (11)
H7A	0.5765	0.3942	0.1437	0.080*
C8	0.4558 (6)	0.4367 (4)	0.3247 (4)	0.0547 (13)
H8A	0.4719	0.5060	0.3361	0.080*
H8B	0.5515	0.4040	0.3476	0.080*
C9	0.3503 (5)	0.4006 (4)	0.4057 (4)	0.0496 (12)
H9A	0.3525	0.3302	0.4090	0.080*
H9B	0.3802	0.4253	0.4908	0.080*
C10	0.0721 (6)	0.3844 (4)	0.3888 (4)	0.0528 (12)
H10A	0.0642	0.4059	0.4722	0.080*
H10B	0.0892	0.3149	0.3914	0.080*
C11	−0.0695 (6)	0.4069 (4)	0.2956 (5)	0.0567 (13)
H11A	−0.1509	0.3669	0.3114	0.080*
H11B	−0.0959	0.4745	0.3032	0.080*
H1WA	0.048 (2)	0.599 (4)	0.097 (5)	0.08 (2)*
H1WB	0.172 (6)	0.624 (4)	0.188 (5)	0.12 (3)*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
Fe1	0.0318 (3)	0.0363 (3)	0.0189 (3)	−0.0006 (2)	0.0027 (2)	−0.0019 (2)
Cl1	0.0710 (8)	0.0529 (7)	0.0534 (7)	0.0022 (6)	0.0102 (6)	−0.0102 (6)
O1W	0.0450 (19)	0.052 (2)	0.0478 (19)	0.0043 (16)	0.0055 (15)	0.0033 (17)
O1	0.0414 (17)	0.082 (2)	0.0351 (16)	0.0081 (16)	0.0050 (13)	−0.0128 (16)
N1	0.047 (2)	0.045 (2)	0.0341 (18)	−0.0073 (17)	0.0008 (16)	0.0000 (16)
N2	0.066 (3)	0.039 (2)	0.037 (2)	0.0004 (18)	0.0105 (18)	−0.0015 (16)
N3	0.053 (2)	0.054 (2)	0.039 (2)	0.0003 (19)	0.0101 (17)	0.0012 (17)
C1	0.047 (2)	0.037 (2)	0.033 (2)	0.0022 (19)	0.0076 (18)	0.0016 (18)
C2	0.056 (3)	0.044 (2)	0.035 (2)	0.004 (2)	0.009 (2)	0.0016 (19)
C3	0.073 (3)	0.043 (3)	0.040 (2)	0.004 (2)	0.020 (2)	0.005 (2)
C4	0.064 (3)	0.057 (3)	0.054 (3)	−0.004 (3)	0.029 (3)	0.003 (2)
C5	0.048 (3)	0.056 (3)	0.054 (3)	−0.004 (2)	0.019 (2)	0.004 (2)
C6	0.043 (2)	0.039 (2)	0.040 (2)	−0.0028 (19)	0.0094 (19)	0.0029 (19)
C7	0.044 (2)	0.047 (3)	0.045 (3)	−0.002 (2)	0.005 (2)	0.005 (2)
C8	0.060 (3)	0.061 (3)	0.037 (2)	−0.017 (2)	−0.003 (2)	−0.002 (2)
C9	0.062 (3)	0.051 (3)	0.030 (2)	−0.004 (2)	−0.002 (2)	−0.002 (2)
C10	0.068 (3)	0.054 (3)	0.040 (3)	0.004 (2)	0.019 (2)	0.004 (2)
C11	0.062 (3)	0.064 (3)	0.048 (3)	0.012 (3)	0.020 (2)	0.004 (2)

Geometric parameters (Å, º)

Fe1—O1	1.907 (3)	C2—H2A	0.9616
Fe1—N1	1.924 (4)	C3—C4	1.387 (7)
Fe1—N2	2.000 (4)	C3—H3A	0.9639
Fe1—N3	2.008 (4)	C4—C5	1.381 (7)
Fe1—O1W	2.306 (4)	C4—H4A	0.9625
O1W—H1WA	0.85 (6)	C5—C6	1.398 (6)
O1W—H1WB	0.85 (6)	C5—H5A	0.9615
O1—C1	1.325 (5)	C6—C7	1.440 (6)
N1—C7	1.272 (6)	C7—H7A	0.9614
N1—C8	1.465 (5)	C8—C9	1.506 (7)
N2—C10	1.467 (6)	C8—H8A	0.9632
N2—C9	1.473 (6)	C8—H8B	0.9617
N2—H2N	0.9047	C9—H9A	0.9633
N3—C11	1.490 (6)	C9—H9B	0.9639
N3—H3NA	0.9859	C10—C11	1.490 (7)
N3—H3NB	0.9230	C10—H10A	0.9639
C1—C6	1.400 (6)	C10—H10B	0.9632
C1—C2	1.402 (6)	C11—H11A	0.9621
C2—C3	1.359 (6)	C11—H11B	0.9631
O1—Fe1—N1	93.09 (14)	C4—C3—H3A	119.7
O1—Fe1—N2	174.17 (16)	C5—C4—C3	118.6 (5)
N1—Fe1—N2	85.19 (16)	C5—C4—H4A	120.6
O1—Fe1—N3	95.28 (14)	C3—C4—H4A	120.8
N1—Fe1—N3	162.29 (16)	C4—C5—C6	121.8 (5)
N2—Fe1—N3	84.92 (16)	C4—C5—H5A	119.4
O1—Fe1—O1W	93.39 (14)	C6—C5—H5A	118.8
N1—Fe1—O1W	98.52 (14)	C5—C6—C1	118.9 (4)
N2—Fe1—O1W	92.38 (14)	C5—C6—C7	117.3 (4)
N3—Fe1—O1W	96.54 (15)	C1—C6—C7	123.8 (4)
Fe1—O1W—H1WA	112 (4)	N1—C7—C6	125.3 (4)
Fe1—O1W—H1WB	118 (5)	N1—C7—H7A	117.3
H1WA—O1W—H1WB	108 (3)	C6—C7—H7A	117.4
C1—O1—Fe1	127.7 (3)	N1—C8—C9	108.0 (4)
C7—N1—C8	120.8 (4)	N1—C8—H8A	110.3
C7—N1—Fe1	126.8 (3)	C9—C8—H8A	110.2
C8—N1—Fe1	112.3 (3)	N1—C8—H8B	109.6
C10—N2—C9	116.4 (4)	C9—C8—H8B	110.1
C10—N2—Fe1	108.4 (3)	H8A—C8—H8B	108.7
C9—N2—Fe1	107.6 (3)	N2—C9—C8	107.8 (4)
C10—N2—H2N	105.3	N2—C9—H9A	109.9
C9—N2—H2N	112.0	C8—C9—H9A	109.8
Fe1—N2—H2N	106.8	N2—C9—H9B	110.3
C11—N3—Fe1	108.9 (3)	C8—C9—H9B	110.6
C11—N3—H3NA	111.3	H9A—C9—H9B	108.4
Fe1—N3—H3NA	110.3	N2—C10—C11	108.1 (4)
C11—N3—H3NB	116.3	N2—C10—H10A	110.4
Fe1—N3—H3NB	103.5	C11—C10—H10A	110.4
H3NA—N3—H3NB	106.2	N2—C10—H10B	109.9
O1—C1—C6	123.2 (4)	C11—C10—H10B	109.6
O1—C1—C2	118.5 (4)	H10A—C10—H10B	108.4
C6—C1—C2	118.3 (4)	N3—C11—C10	109.3 (4)
C3—C2—C1	121.7 (5)	N3—C11—H11A	110.1
C3—C2—H2A	119.6	C10—C11—H11A	110.3
C1—C2—H2A	118.7	N3—C11—H11B	108.9
C2—C3—C4	120.6 (5)	C10—C11—H11B	109.6
C2—C3—H3A	119.7	H11A—C11—H11B	108.5
N1—Fe1—O1—C1	4.0 (4)	Fe1—O1—C1—C2	176.5 (3)
N2—Fe1—O1—C1	−68.7 (16)	O1—C1—C2—C3	−179.0 (4)
N3—Fe1—O1—C1	−160.4 (4)	C6—C1—C2—C3	0.7 (7)
O1W—Fe1—O1—C1	102.8 (4)	C1—C2—C3—C4	−0.9 (7)
O1—Fe1—N1—C7	−3.4 (4)	C2—C3—C4—C5	0.4 (7)
N2—Fe1—N1—C7	171.0 (4)	C3—C4—C5—C6	0.2 (7)
N3—Fe1—N1—C7	114.8 (6)	C4—C5—C6—C1	−0.3 (7)
O1W—Fe1—N1—C7	−97.3 (4)	C4—C5—C6—C7	178.9 (4)
O1—Fe1—N1—C8	178.4 (3)	O1—C1—C6—C5	179.6 (4)
N2—Fe1—N1—C8	−7.2 (3)	C2—C1—C6—C5	−0.1 (6)
N3—Fe1—N1—C8	−63.5 (6)	O1—C1—C6—C7	0.4 (7)
O1W—Fe1—N1—C8	84.5 (3)	C2—C1—C6—C7	−179.3 (4)
O1—Fe1—N2—C10	−72.7 (15)	C8—N1—C7—C6	−179.9 (4)
N1—Fe1—N2—C10	−145.8 (3)	Fe1—N1—C7—C6	2.0 (7)
N3—Fe1—N2—C10	19.5 (3)	C5—C6—C7—N1	−179.0 (4)
O1W—Fe1—N2—C10	115.9 (3)	C1—C6—C7—N1	0.2 (7)
O1—Fe1—N2—C9	53.9 (16)	C7—N1—C8—C9	−146.8 (4)
N1—Fe1—N2—C9	−19.2 (3)	Fe1—N1—C8—C9	31.5 (5)
N3—Fe1—N2—C9	146.1 (3)	C10—N2—C9—C8	162.5 (4)
O1W—Fe1—N2—C9	−117.5 (3)	Fe1—N2—C9—C8	40.7 (4)
O1—Fe1—N3—C11	−178.7 (3)	N1—C8—C9—N2	−47.2 (5)
N1—Fe1—N3—C11	63.4 (6)	C9—N2—C10—C11	−163.5 (4)
N2—Fe1—N3—C11	7.1 (3)	Fe1—N2—C10—C11	−42.2 (4)
O1W—Fe1—N3—C11	−84.7 (3)	Fe1—N3—C11—C10	−32.3 (5)
Fe1—O1—C1—C6	−3.2 (6)	N2—C10—C11—N3	49.4 (5)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
O1W—H1WA···O1^i	0.84 (1)	1.84 (1)	2.675 (5)	169 (5)
O1W—H1WB···Cl1	0.85 (6)	2.36 (4)	3.124 (4)	151 (7)
N2—H2N···Cl1	0.90	2.36	3.253 (4)	170
N3—H3NA···Cl1^ii	0.99	2.39	3.340 (4)	162
N3—H3NB···O1W^i	0.92	2.43	3.115 (5)	131

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