Bis(ethyl­enediamine-κ²N,N′)(2-oxido-5-sulfonatobenzoato-κ²O¹,O²)chromium(III) dihydrate

In the title compound, [Cr(C₇H₃O₆S)(C₂H₈N₂)₂]·2H₂O, the chromium(III) ion is at the centre of a compressed octa­hedron formed by four N atoms [Cr—N = 2.060 (5)–2.107 (5) Å] from two ethyl­enediamine mol­ecules, one phenolate O atom [Cr—O = 1.899 (4) Å] and a carboxyl­ate O atom [Cr—O = 1.929 (4) Å] from the 2-oxido-5-sulfonatobenzoate ligand. These two O atoms and two of the N atoms occupy the equatorial positions and the remaining N atoms occupy the axial positions. The crystal structure is stabilized by a number of inter­molecular hydrogen bonds.

Key indicators

• Single-crystal X-ray study
• T = 293 K
• Mean [sigma](C-C) = 0.009 Å
• R factor = 0.087
• wR factor = 0.152
• Data-to-parameter ratio = 13.5

checkCIF/PLATON results

No syntax errors found



Alert level B
PLAT420_ALERT_2_B D-H Without Acceptor       O8     -   H23    ...          ?

Alert level C
PLAT042_ALERT_1_C Calc. and Rep. MoietyFormula Strings Differ ....          ?
PLAT125_ALERT_4_C No _symmetry_space_group_name_Hall Given .......          ?
PLAT152_ALERT_1_C Supplied and Calc Volume s.u. Inconsistent .....          ?
PLAT199_ALERT_1_C Check the Reported _cell_measurement_temperature        293 K
PLAT200_ALERT_1_C Check the Reported _diffrn_ambient_temperature .        293 K
PLAT341_ALERT_3_C Low Bond Precision on C-C bonds (x 1000) Ang ...          9
PLAT420_ALERT_2_C D-H Without Acceptor       N4     -   H5     ...          ?
PLAT480_ALERT_4_C Long H...A H-Bond Reported H13    ..  S2      ..       2.98 Ang.
PLAT480_ALERT_4_C Long H...A H-Bond Reported H11    ..  S2      ..       2.98 Ang.
PLAT480_ALERT_4_C Long H...A H-Bond Reported H21    ..  S2      ..       2.93 Ang.
PLAT481_ALERT_4_C Long D...A H-Bond Reported N2     ..  S2      ..       3.87 Ang.

Alert level G
FORMU01_ALERT_1_G  There is a discrepancy between the atom counts in the
            _chemical_formula_sum and _chemical_formula_moiety. This is
            usually due to the moiety formula being in the wrong format.
            Atom count from _chemical_formula_sum:   C11 H23 Cr1 N4 O8 S1
            Atom count from _chemical_formula_moiety:C11 H27 Cr1 N4 O10 S1

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

   5 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
   2 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

---

Computing details

Data collection: SMART (Bruker, 2000); cell refinement: SMART; data reduction: SAINT (Bruker, 2000); program(s) used to solve structure: SHELXS97 (Sheldrick, 2000); program(s) used to refine structure: SHELXL97 (Sheldrick, 2000); molecular graphics: SHELXTL (Sheldrick, 1999); software used to prepare material for publication: SHELXTL.

Bis(ethylenediamine-κ²N,N')(2-oxido-5-sulfonatobenzoato- κ²O¹,O²)chromium(III) dihydrate

Crystal data

[Cr(C7H3O6S)(C2H8N2)2]·2H2O	F(000) = 884
Mr = 423.39	Dx = 1.604 Mg m^−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
a = 11.995 (3) Å	θ = 2.5–26.9°
b = 10.138 (3) Å	µ = 0.82 mm^−1
c = 14.933 (4) Å	T = 293 K
β = 105.081 (4)°	Block, red
V = 1753.4 (9) Å^3	0.40 × 0.10 × 0.10 mm
Z = 4

Data collection

Bruker SMART CCD area-detector diffractometer	3061 independent reflections
Radiation source: fine-focus sealed tube	2772 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.043
φ and ω scans	θmax = 25.0°, θmin = 1.8°
Absorption correction: multi-scan (SADABS; Sheldrick, 2000)	h = −14→14
Tmin = 0.735, Tmax = 0.923	k = −12→11
6966 measured reflections	l = −17→14

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)] = 0.087	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.152	H-atom parameters constrained
S = 1.31	w = 1/[σ^2(Fo^2) + (0.0255P)^2 + 6.1162P] where P = (Fo^2 + 2Fc^2)/3
3061 reflections	(Δ/σ)max < 0.001
226 parameters	Δρmax = 0.56 e Å^−3
0 restraints	Δρmin = −0.56 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
Cr1	0.26449 (7)	0.52022 (9)	0.19039 (7)	0.0202 (3)
O1	0.1626 (3)	0.4252 (4)	0.2450 (3)	0.0280 (10)
O2	0.1379 (3)	0.6120 (4)	0.1076 (3)	0.0279 (10)
O3	−0.0391 (3)	0.6593 (4)	0.0331 (3)	0.0312 (10)
C1	0.0555 (5)	0.4589 (5)	0.2413 (4)	0.0238 (13)
C2	0.0072 (5)	0.4048 (6)	0.3096 (5)	0.0284 (14)
H1	0.0519	0.3496	0.3546	0.034*
C3	−0.1038 (5)	0.4317 (6)	0.3110 (5)	0.0324 (15)
H2	−0.1344	0.3935	0.3559	0.039*
C4	−0.1708 (5)	0.5157 (6)	0.2458 (4)	0.0261 (14)
C5	−0.1253 (5)	0.5698 (5)	0.1784 (4)	0.0226 (13)
H3	−0.1713	0.6251	0.1342	0.027*
C6	−0.0129 (4)	0.5446 (5)	0.1745 (4)	0.0214 (13)
C7	0.0292 (5)	0.6074 (5)	0.0993 (4)	0.0241 (13)
C8	0.3550 (6)	0.5536 (7)	0.0296 (5)	0.0381 (17)
H14	0.4170	0.5784	0.0022	0.057*
H15	0.2822	0.5788	−0.0128	0.057*
C9	0.3573 (5)	0.4073 (7)	0.0463 (5)	0.0365 (16)
H16	0.3440	0.3600	−0.0120	0.055*
H17	0.4317	0.3810	0.0857	0.055*
C10	0.4064 (5)	0.6333 (6)	0.3619 (5)	0.0351 (16)
H6	0.4109	0.6761	0.4208	0.053*
H7	0.4683	0.6668	0.3375	0.053*
N1	0.2644 (4)	0.3774 (5)	0.0922 (3)	0.0263 (12)
H18	0.2765	0.2976	0.1194	0.039*
H19	0.1955	0.3761	0.0499	0.039*
N2	0.3692 (4)	0.6206 (5)	0.1191 (4)	0.0301 (12)
H12	0.3472	0.7055	0.1102	0.045*
H13	0.4436	0.6181	0.1520	0.045*
N3	0.3990 (4)	0.4241 (5)	0.2831 (3)	0.0232 (11)
H10	0.3815	0.3383	0.2868	0.035*
H11	0.4637	0.4297	0.2636	0.035*
N4	0.2938 (4)	0.6607 (5)	0.2963 (4)	0.0280 (12)
H4	0.2939	0.7422	0.2723	0.042*
H5	0.2374	0.6568	0.3259	0.042*
S2	−0.31383 (12)	0.54914 (14)	0.25005 (12)	0.0266 (4)
O4	−0.3627 (3)	0.6422 (4)	0.1784 (3)	0.0357 (11)
O5	−0.3743 (3)	0.4231 (4)	0.2357 (3)	0.0374 (12)
O6	−0.3078 (4)	0.6000 (4)	0.3419 (3)	0.0396 (12)
O7	0.7120 (4)	0.3798 (5)	0.4694 (4)	0.0570 (15)
H20	0.7766	0.3632	0.5073	0.085*
H21	0.7172	0.4496	0.4393	0.085*
O8	0.0786 (5)	0.7972 (6)	0.9194 (4)	0.079 (2)
H22	0.0597	0.7594	0.9641	0.118*
H23	0.0217	0.8415	0.8879	0.118*
C11	0.4175 (6)	0.4868 (6)	0.3748 (5)	0.0373 (16)
H8	0.4937	0.4649	0.4132	0.056*
H9	0.3607	0.4549	0.4055	0.056*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
Cr1	0.0161 (5)	0.0187 (5)	0.0273 (5)	0.0001 (4)	0.0084 (4)	0.0032 (4)
O1	0.020 (2)	0.026 (2)	0.042 (3)	0.0033 (17)	0.014 (2)	0.009 (2)
O2	0.018 (2)	0.029 (2)	0.038 (3)	0.0030 (17)	0.0089 (19)	0.010 (2)
O3	0.026 (2)	0.036 (3)	0.030 (3)	0.0030 (19)	0.005 (2)	0.010 (2)
C1	0.019 (3)	0.017 (3)	0.040 (4)	−0.002 (2)	0.016 (3)	−0.005 (3)
C2	0.023 (3)	0.026 (3)	0.037 (4)	0.005 (3)	0.009 (3)	0.009 (3)
C3	0.037 (4)	0.023 (3)	0.045 (4)	−0.002 (3)	0.023 (3)	0.006 (3)
C4	0.016 (3)	0.024 (3)	0.040 (4)	0.002 (2)	0.010 (3)	−0.004 (3)
C5	0.018 (3)	0.023 (3)	0.024 (3)	−0.005 (2)	0.002 (2)	−0.006 (3)
C6	0.019 (3)	0.018 (3)	0.029 (3)	0.001 (2)	0.009 (3)	−0.007 (3)
C7	0.030 (3)	0.019 (3)	0.026 (3)	0.000 (3)	0.011 (3)	−0.003 (3)
C8	0.038 (4)	0.046 (4)	0.036 (4)	0.005 (3)	0.018 (3)	0.012 (3)
C9	0.031 (4)	0.049 (4)	0.034 (4)	0.008 (3)	0.016 (3)	−0.002 (3)
C10	0.039 (4)	0.030 (4)	0.036 (4)	−0.003 (3)	0.009 (3)	−0.005 (3)
N1	0.021 (3)	0.026 (3)	0.028 (3)	0.002 (2)	−0.001 (2)	0.000 (2)
N2	0.023 (3)	0.031 (3)	0.039 (3)	0.000 (2)	0.011 (2)	0.010 (3)
N3	0.019 (2)	0.022 (3)	0.028 (3)	0.001 (2)	0.005 (2)	0.004 (2)
N4	0.032 (3)	0.021 (3)	0.037 (3)	−0.002 (2)	0.018 (3)	0.002 (2)
S2	0.0195 (7)	0.0201 (8)	0.0428 (10)	0.0003 (6)	0.0127 (7)	−0.0038 (7)
O4	0.027 (2)	0.033 (3)	0.049 (3)	0.0099 (19)	0.014 (2)	0.003 (2)
O5	0.016 (2)	0.034 (2)	0.069 (3)	−0.0052 (18)	0.022 (2)	−0.012 (2)
O6	0.041 (3)	0.035 (3)	0.050 (3)	−0.005 (2)	0.026 (2)	−0.012 (2)
O7	0.061 (3)	0.048 (3)	0.072 (4)	0.002 (3)	0.034 (3)	0.006 (3)
O8	0.078 (4)	0.085 (5)	0.068 (4)	−0.012 (4)	0.010 (3)	0.032 (4)
C11	0.039 (4)	0.040 (4)	0.033 (4)	0.001 (3)	0.010 (3)	0.000 (3)

Geometric parameters (Å, º)

Cr1—O1	1.899 (4)	C9—H16	0.9700
Cr1—O2	1.929 (4)	C9—H17	0.9700
Cr1—N1	2.060 (5)	C10—N4	1.474 (8)
Cr1—N3	2.075 (5)	C10—C11	1.499 (9)
Cr1—N4	2.089 (5)	C10—H6	0.9700
Cr1—N2	2.107 (5)	C10—H7	0.9700
O1—C1	1.316 (6)	N1—H18	0.9000
O2—C7	1.278 (7)	N1—H19	0.9000
O3—C7	1.226 (7)	N2—H12	0.9000
C1—C2	1.409 (8)	N2—H13	0.9000
C1—C6	1.413 (8)	N3—C11	1.473 (8)
C2—C3	1.364 (8)	N3—H10	0.9000
C2—H1	0.9300	N3—H11	0.9000
C3—C4	1.383 (8)	N4—H4	0.9000
C3—H2	0.9300	N4—H5	0.9000
C4—C5	1.376 (8)	S2—O4	1.433 (5)
C4—S2	1.767 (5)	S2—O6	1.449 (5)
C5—C6	1.389 (7)	S2—O5	1.457 (4)
C5—H3	0.9300	O7—H20	0.8496
C6—C7	1.488 (8)	O7—H21	0.8495
C8—N2	1.470 (8)	O8—H22	0.8508
C8—C9	1.503 (9)	O8—H23	0.8495
C8—H14	0.9700	C11—H8	0.9700
C8—H15	0.9700	C11—H9	0.9700
C9—N1	1.484 (7)
O1—Cr1—O2	91.85 (17)	N1—C9—H17	110.3
O1—Cr1—N1	93.87 (19)	C8—C9—H17	110.3
O2—Cr1—N1	91.64 (19)	H16—C9—H17	108.5
O1—Cr1—N3	87.18 (18)	N4—C10—C11	107.9 (5)
O2—Cr1—N3	178.08 (19)	N4—C10—H6	110.1
N1—Cr1—N3	90.08 (19)	C11—C10—H6	110.1
O1—Cr1—N4	91.21 (18)	N4—C10—H7	110.1
O2—Cr1—N4	96.05 (19)	C11—C10—H7	110.1
N1—Cr1—N4	170.65 (19)	H6—C10—H7	108.4
N3—Cr1—N4	82.32 (19)	C9—N1—Cr1	108.9 (4)
O1—Cr1—N2	175.3 (2)	C9—N1—H18	109.9
O2—Cr1—N2	85.23 (18)	Cr1—N1—H18	109.9
N1—Cr1—N2	82.6 (2)	C9—N1—H19	109.9
N3—Cr1—N2	95.84 (19)	Cr1—N1—H19	109.9
N4—Cr1—N2	92.8 (2)	H18—N1—H19	108.3
C1—O1—Cr1	125.5 (4)	C8—N2—Cr1	107.0 (4)
C7—O2—Cr1	131.2 (4)	C8—N2—H12	110.3
O1—C1—C2	116.7 (5)	Cr1—N2—H12	110.3
O1—C1—C6	124.8 (5)	C8—N2—H13	110.3
C2—C1—C6	118.6 (5)	Cr1—N2—H13	110.3
C3—C2—C1	121.3 (6)	H12—N2—H13	108.6
C3—C2—H1	119.4	C11—N3—Cr1	108.7 (4)
C1—C2—H1	119.4	C11—N3—H10	109.9
C2—C3—C4	120.2 (6)	Cr1—N3—H10	109.9
C2—C3—H2	119.9	C11—N3—H11	109.9
C4—C3—H2	119.9	Cr1—N3—H11	109.9
C5—C4—C3	119.5 (5)	H10—N3—H11	108.3
C5—C4—S2	121.6 (5)	C10—N4—Cr1	108.6 (4)
C3—C4—S2	119.0 (5)	C10—N4—H4	110.0
C4—C5—C6	122.1 (6)	Cr1—N4—H4	110.0
C4—C5—H3	119.0	C10—N4—H5	110.0
C6—C5—H3	119.0	Cr1—N4—H5	110.0
C5—C6—C1	118.4 (5)	H4—N4—H5	108.4
C5—C6—C7	118.5 (5)	O4—S2—O6	112.5 (3)
C1—C6—C7	123.2 (5)	O4—S2—O5	112.1 (3)
O3—C7—O2	120.9 (5)	O6—S2—O5	110.6 (3)
O3—C7—C6	120.4 (5)	O4—S2—C4	108.1 (3)
O2—C7—C6	118.6 (5)	O6—S2—C4	107.0 (3)
N2—C8—C9	108.2 (5)	O5—S2—C4	106.1 (3)
N2—C8—H14	110.1	H20—O7—H21	109.7
C9—C8—H14	110.1	H22—O8—H23	109.5
N2—C8—H15	110.1	N3—C11—C10	108.7 (5)
C9—C8—H15	110.1	N3—C11—H8	110.0
H14—C8—H15	108.4	C10—C11—H8	110.0
N1—C9—C8	107.2 (5)	N3—C11—H9	110.0
N1—C9—H16	110.3	C10—C11—H9	110.0
C8—C9—H16	110.3	H8—C11—H9	108.3

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H18···O6^i	0.90	2.09	2.980 (6)	169
N1—H19···O3^ii	0.90	1.99	2.884 (6)	169
N2—H12···O7^iii	0.90	2.14	2.988 (7)	156
N2—H13···O4^iv	0.90	2.27	3.114 (6)	157
N2—H13···S2^iv	0.90	2.98	3.865 (5)	168
N3—H10···O4^i	0.90	2.08	2.970 (6)	169
N3—H11···O5^iv	0.90	2.09	2.983 (6)	171
N3—H11···S2^iv	0.90	2.98	3.821 (5)	155
N4—H4···O5^v	0.90	2.09	2.912 (6)	151
O7—H20···O8^vi	0.85	1.92	2.758 (8)	170
O7—H21···O6^iv	0.85	2.07	2.904 (7)	165
O7—H21···S2^iv	0.85	2.93	3.639 (6)	142
O8—H22···O3^vii	0.85	2.03	2.842 (7)	159
O8—H22···O2^vii	0.85	2.58	3.301 (7)	143

Symmetry codes: (i) −x, y−1/2, −z+1/2; (ii) −x, −y+1, −z; (iii) −x+1, y+1/2, −z+1/2; (iv) x+1, y, z; (v) −x, y+1/2, −z+1/2; (vi) −x+1, y−1/2, −z+3/2; (vii) x, y, z+1.