Δ_L-(L-Cysteinato-κ²N,S)bis­(ethyl­enediamine-κ²N,N′)cobalt(III) bis(perchlorate) monohydrate

In the title compound, [Co(C₃H₆NO₂S)(C₂H₈N₂)₂](ClO₄)₂·H₂O, the central Co^III atom is coordinated by one N,S-bidentate L-cysteine (L-H₂cys) and two N,N′-bidentate ethyl­enediamine (en) ligands in a slightly distorted octa­hedral geometry with a Δ configuration. The L-Hcys chelate ring adopts a λ conformation, while the two en chelate rings have a δ conformation.

Key indicators

• Single-crystal X-ray study
• T = 296 K
• Mean [sigma](C-C) = 0.004 Å
• R factor = 0.036
• wR factor = 0.099
• Data-to-parameter ratio = 21.3

checkCIF/PLATON results

No syntax errors found



Alert level C
PLAT062_ALERT_4_C Rescale T(min) & T(max) by .....................       0.96
PLAT232_ALERT_2_C Hirshfeld Test Diff (M-X)  Co1    -   S1      ..       5.25 su
PLAT244_ALERT_4_C Low   'Solvent' Ueq as Compared to Neighbors for        Cl1
PLAT244_ALERT_4_C Low   'Solvent' Ueq as Compared to Neighbors for        Cl2
PLAT420_ALERT_2_C D-H Without Acceptor       N3     -   H6     ...          ?
PLAT420_ALERT_2_C D-H Without Acceptor       N3     -   H7     ...          ?
PLAT420_ALERT_2_C D-H Without Acceptor       N4     -   H8     ...          ?
PLAT480_ALERT_4_C Long H...A H-Bond Reported H7     ..  O8      ..       2.67 Ang.
PLAT480_ALERT_4_C Long H...A H-Bond Reported H6     ..  O8      ..       2.61 Ang.
PLAT731_ALERT_1_C Bond    Calc     0.81(4), Rep   0.809(19) ......       2.11 su-Ra
              O2   -H1      1.555   1.555
PLAT731_ALERT_1_C Bond    Calc     0.81(4), Rep   0.809(18) ......       2.22 su-Ra
              O11  -H23     1.555   1.555
PLAT735_ALERT_1_C D-H     Calc     0.81(4), Rep   0.809(19) ......       2.11 su-Ra
              O2   -H1      1.555   1.555

Alert level G
REFLT03_ALERT_4_G Please check that the estimate of the number of Friedel pairs is
            correct. If it is not, please give the correct count in the
            _publ_section_exptl_refinement section of the submitted CIF.
           From the CIF: _diffrn_reflns_theta_max           29.99
           From the CIF: _reflns_number_total               5431
           Count of symmetry unique reflns         3066
           Completeness (_total/calc)            177.14%
           TEST3: Check Friedels for noncentro structure
           Estimate of Friedel pairs measured      2365
           Fraction of Friedel pairs measured     0.771
           Are heavy atom types Z>Si present        yes
PLAT791_ALERT_1_G Confirm the Absolute Configuration of C2     = .          R

   0 ALERT level A = In general: serious problem
   0 ALERT level B = Potentially serious problem
  12 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
   4 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
   6 ALERT type 4 Improvement, methodology, query or suggestion
   0 ALERT type 5 Informative message, check

---

Computing details

Data collection: WinAFC (Rigaku/MSC, 2004); cell refinement: WinAFC; data reduction: CrystalStructure (Rigaku/MSC, 2004); program(s) used to solve structure: SIR92 (Altomare et al., 1994); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997); software used to prepare material for publication: WinGX (Farrugia, 1999).

Δ_L-(L-Cysteinato-κ²N,S)bis(ethylenediamine-κ²N,N')cobalt(III) bis(perchlorate) monohydrate

Crystal data

[Co(C3H6NO2S)(C2H8N2)2](ClO4)2·H2O	F(000) = 1064
Mr = 516.21	Dx = 1.835 Mg m^−3
Orthorhombic, P212121	Mo Kα radiation, λ = 0.71069 Å
Hall symbol: P 2ac 2ab	Cell parameters from 25 reflections
a = 11.987 (4) Å	θ = 12.5–14.9°
b = 16.926 (6) Å	µ = 1.38 mm^−1
c = 9.209 (3) Å	T = 296 K
V = 1868.5 (12) Å^3	Prism, dark brown
Z = 4	0.60 × 0.40 × 0.32 mm

Data collection

Rigaku AFC-7R diffractometer	5056 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	Rint = 0.027
Graphite monochromator	θmax = 30.0°, θmin = 2.5°
ω–2θ scans	h = −7→16
Absorption correction: ψ scan (North et al., 1968)	k = 0→23
Tmin = 0.491, Tmax = 0.666	l = −12→12
6218 measured reflections	3 standard reflections every 150 reflections
5431 independent reflections	intensity decay: 1.0%

Refinement

Refinement on F^2	Hydrogen site location: inferred from neighbouring sites
Least-squares matrix: full	H atoms treated by a mixture of independent and constrained refinement
R[F^2 > 2σ(F^2)] = 0.036	w = 1/[σ^2(Fo^2) + (0.0657P)^2 + 0.6912P] where P = (Fo^2 + 2Fc^2)/3
wR(F^2) = 0.099	(Δ/σ)max < 0.001
S = 1.07	Δρmax = 0.78 e Å^−3
5431 reflections	Δρmin = −0.77 e Å^−3
255 parameters	Extinction correction: SHELXL97, Fc^*=kFc[1+0.001xFc^2λ^3/sin(2θ)]^-1/4
4 restraints	Extinction coefficient: 0.0237 (14)
Primary atom site location: structure-invariant direct methods	Absolute structure: Flack (1983), no Friedel pairs
Secondary atom site location: difference Fourier map	Absolute structure parameter: −0.004 (12)

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
Co1	0.47672 (2)	0.103004 (16)	0.37721 (3)	0.02071 (8)
S1	0.48017 (5)	0.00569 (3)	0.54160 (6)	0.02847 (12)
O1	0.73762 (19)	0.22769 (12)	0.6910 (2)	0.0368 (4)
O2	0.7443 (2)	0.11823 (15)	0.8247 (2)	0.0463 (5)
H1	0.800 (3)	0.144 (3)	0.841 (6)	0.069*
N1	0.58312 (17)	0.16183 (12)	0.5033 (2)	0.0246 (4)
H2	0.6496	0.1640	0.4581	0.029*
H3	0.5584	0.2117	0.5135	0.029*
N2	0.34975 (16)	0.15071 (13)	0.4773 (2)	0.0261 (4)
H4	0.3633	0.1527	0.5734	0.031*
H5	0.3395	0.2004	0.4453	0.031*
N3	0.36294 (19)	0.04459 (13)	0.2647 (2)	0.0296 (4)
H6	0.3790	0.0474	0.1693	0.036*
H7	0.3632	−0.0066	0.2910	0.036*
N4	0.4808 (2)	0.18783 (12)	0.2231 (2)	0.0288 (4)
H8	0.4110	0.2002	0.1953	0.035*
H9	0.5134	0.2317	0.2586	0.035*
N5	0.60096 (19)	0.05560 (13)	0.2663 (2)	0.0303 (4)
H10	0.6566	0.0426	0.3275	0.036*
H11	0.5773	0.0112	0.2224	0.036*
C1	0.6036 (2)	0.03793 (15)	0.6383 (3)	0.0337 (5)
H12	0.6054	0.0145	0.7344	0.040*
H13	0.6701	0.0217	0.5863	0.040*
C2	0.59957 (19)	0.12723 (14)	0.6499 (2)	0.0270 (4)
H25	0.5350	0.1410	0.7082	0.032*
C3	0.7027 (2)	0.16370 (16)	0.7228 (3)	0.0288 (4)
C4	0.2481 (2)	0.10318 (17)	0.4495 (3)	0.0328 (5)
H15	0.1818	0.1342	0.4696	0.039*
H16	0.2473	0.0567	0.5113	0.039*
C5	0.2509 (2)	0.07926 (17)	0.2920 (3)	0.0336 (5)
H17	0.1930	0.0407	0.2720	0.040*
H18	0.2389	0.1249	0.2302	0.040*
C6	0.5454 (2)	0.15750 (18)	0.0972 (3)	0.0366 (6)
H19	0.5713	0.2011	0.0377	0.044*
H20	0.4988	0.1235	0.0378	0.044*
C7	0.6432 (2)	0.1117 (2)	0.1558 (3)	0.0399 (6)
H21	0.6797	0.0831	0.0778	0.048*
H22	0.6969	0.1474	0.1991	0.048*
Cl1	0.43393 (5)	0.38458 (4)	0.54580 (7)	0.03353 (14)
O3	0.4579 (2)	0.31652 (17)	0.4617 (4)	0.0647 (8)
O4	0.4796 (3)	0.3719 (3)	0.6884 (3)	0.0772 (9)
O5	0.31590 (19)	0.39700 (19)	0.5564 (4)	0.0599 (7)
O6	0.4840 (3)	0.45364 (17)	0.4913 (4)	0.0744 (9)
Cl2	0.26380 (6)	0.16612 (4)	0.87287 (8)	0.04103 (15)
O7	0.3542 (3)	0.2061 (2)	0.8029 (4)	0.0763 (10)
O8	0.3005 (5)	0.0894 (2)	0.9164 (6)	0.1076 (17)
O9	0.2367 (3)	0.20894 (19)	1.0015 (3)	0.0648 (8)
O10	0.1703 (4)	0.1601 (4)	0.7822 (5)	0.117 (2)
O11	0.9151 (2)	0.16773 (14)	0.9737 (3)	0.0442 (5)
H23	0.956 (4)	0.1321 (19)	0.998 (5)	0.066*
H24	0.936 (4)	0.2133 (12)	0.978 (5)	0.066*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
Co1	0.02155 (13)	0.02132 (13)	0.01927 (13)	−0.00031 (10)	0.00091 (10)	0.00089 (10)
S1	0.0311 (2)	0.0245 (2)	0.0298 (3)	−0.0043 (2)	−0.0023 (2)	0.00591 (19)
O1	0.0431 (10)	0.0327 (9)	0.0347 (9)	−0.0092 (8)	−0.0045 (8)	−0.0006 (7)
O2	0.0498 (12)	0.0514 (13)	0.0376 (10)	−0.0178 (10)	−0.0195 (9)	0.0159 (9)
N1	0.0257 (8)	0.0237 (8)	0.0243 (8)	−0.0007 (7)	−0.0014 (6)	0.0035 (7)
N2	0.0234 (8)	0.0313 (10)	0.0237 (9)	0.0015 (7)	0.0002 (7)	−0.0014 (7)
N3	0.0336 (10)	0.0292 (10)	0.0260 (9)	−0.0057 (8)	−0.0033 (8)	−0.0031 (8)
N4	0.0311 (9)	0.0298 (9)	0.0255 (8)	0.0002 (8)	0.0004 (8)	0.0054 (7)
N5	0.0293 (10)	0.0330 (10)	0.0286 (10)	0.0052 (8)	0.0044 (8)	0.0009 (8)
C1	0.0338 (11)	0.0281 (10)	0.0391 (13)	−0.0034 (9)	−0.0097 (11)	0.0105 (10)
C2	0.0271 (10)	0.0307 (10)	0.0231 (10)	−0.0041 (8)	0.0003 (8)	0.0026 (8)
C3	0.0304 (10)	0.0357 (12)	0.0204 (9)	−0.0009 (9)	0.0016 (8)	−0.0014 (8)
C4	0.0222 (9)	0.0402 (12)	0.0361 (11)	−0.0035 (9)	0.0027 (9)	0.0038 (10)
C5	0.0291 (11)	0.0356 (12)	0.0362 (12)	−0.0049 (9)	−0.0075 (10)	0.0019 (10)
C6	0.0415 (14)	0.0449 (14)	0.0235 (10)	−0.0011 (11)	0.0064 (9)	0.0067 (9)
C7	0.0352 (12)	0.0526 (16)	0.0318 (12)	0.0035 (11)	0.0107 (10)	0.0082 (11)
Cl1	0.0253 (2)	0.0316 (3)	0.0437 (3)	0.0012 (2)	−0.0003 (2)	−0.0082 (2)
O3	0.0596 (16)	0.0517 (14)	0.083 (2)	0.0058 (12)	0.0070 (15)	−0.0282 (14)
O4	0.0695 (18)	0.111 (3)	0.0513 (15)	0.005 (2)	−0.0145 (15)	0.0040 (17)
O5	0.0266 (10)	0.0783 (19)	0.0748 (18)	0.0044 (11)	0.0018 (11)	−0.0245 (16)
O6	0.0655 (17)	0.0442 (13)	0.113 (3)	−0.0041 (13)	0.010 (2)	0.0225 (16)
Cl2	0.0446 (3)	0.0428 (3)	0.0357 (3)	−0.0048 (3)	0.0032 (3)	−0.0117 (3)
O7	0.089 (2)	0.089 (2)	0.0513 (16)	−0.0304 (19)	0.0245 (16)	−0.0117 (16)
O8	0.142 (4)	0.0451 (17)	0.135 (4)	0.007 (2)	−0.003 (4)	−0.008 (2)
O9	0.093 (2)	0.0628 (17)	0.0390 (12)	0.0042 (16)	0.0109 (14)	−0.0150 (11)
O10	0.065 (2)	0.216 (6)	0.070 (2)	0.001 (3)	−0.0267 (18)	−0.051 (3)
O11	0.0448 (11)	0.0430 (11)	0.0449 (12)	0.0037 (9)	−0.0122 (10)	0.0022 (10)

Geometric parameters (Å, º)

Co1—S1	2.2376 (8)	C1—C2	1.516 (4)
Co1—N1	1.991 (2)	C1—H12	0.9700
Co1—N2	1.954 (2)	C1—H13	0.9700
Co1—N3	1.978 (2)	C2—C3	1.536 (3)
Co1—N4	2.019 (2)	C2—H25	0.9700
Co1—N5	1.976 (2)	C4—C5	1.506 (4)
S1—C1	1.811 (3)	C4—H15	0.9700
O1—C3	1.198 (3)	C4—H16	0.9700
O2—C3	1.312 (3)	C5—H17	0.9700
O2—H1	0.809 (19)	C5—H18	0.9700
N1—C2	1.485 (3)	C6—C7	1.505 (4)
N1—H2	0.9000	C6—H19	0.9700
N1—H3	0.9000	C6—H20	0.9700
N2—C4	1.482 (3)	C7—H21	0.9700
N2—H4	0.9000	C7—H22	0.9700
N2—H5	0.9000	Cl1—O6	1.407 (3)
N3—C5	1.487 (4)	Cl1—O3	1.417 (3)
N3—H6	0.9000	Cl1—O5	1.434 (2)
N3—H7	0.9000	Cl1—O4	1.439 (3)
N4—C6	1.486 (3)	Cl2—O10	1.401 (4)
N4—H8	0.9000	Cl2—O9	1.426 (3)
N4—H9	0.9000	Cl2—O8	1.429 (4)
N5—C7	1.481 (4)	Cl2—O7	1.431 (3)
N5—H10	0.9000	O11—H23	0.809 (18)
N5—H11	0.9000	O11—H24	0.810 (18)
S1—Co1—N4	176.78 (7)	C2—C1—H13	110.1
N2—Co1—N5	177.02 (9)	S1—C1—H13	110.1
N2—Co1—N3	85.22 (10)	H12—C1—H13	108.4
N5—Co1—N3	92.64 (10)	N1—C2—C1	109.4 (2)
N2—Co1—N1	90.98 (9)	N1—C2—C3	110.25 (19)
N5—Co1—N1	91.23 (10)	C1—C2—C3	114.0 (2)
N1—Co1—N3	175.60 (9)	N1—C2—H25	107.6
N2—Co1—N4	93.25 (9)	C1—C2—H25	107.6
N5—Co1—N4	84.68 (9)	C3—C2—H25	107.6
N3—Co1—N4	90.24 (10)	O1—C3—O2	124.9 (3)
N1—Co1—N4	92.20 (9)	O1—C3—C2	122.5 (2)
N2—Co1—S1	89.96 (7)	O2—C3—C2	112.5 (2)
N5—Co1—S1	92.10 (7)	N2—C4—C5	107.1 (2)
N3—Co1—S1	89.96 (7)	N2—C4—H15	110.3
N1—Co1—S1	87.81 (6)	C5—C4—H15	110.3
C1—S1—Co1	97.23 (8)	N2—C4—H16	110.3
C3—O2—H1	98 (4)	C5—C4—H16	110.3
C2—N1—Co1	114.71 (14)	H15—C4—H16	108.5
C2—N1—H2	108.6	N3—C5—C4	106.8 (2)
Co1—N1—H2	108.6	N3—C5—H17	110.4
C2—N1—H3	108.6	C4—C5—H17	110.4
Co1—N1—H3	108.6	N3—C5—H18	110.4
H2—N1—H3	107.6	C4—C5—H18	110.4
C4—N2—Co1	109.53 (16)	H17—C5—H18	108.6
C4—N2—H4	109.8	N4—C6—C7	107.7 (2)
Co1—N2—H4	109.8	N4—C6—H19	110.2
C4—N2—H5	109.8	C7—C6—H19	110.2
Co1—N2—H5	109.8	N4—C6—H20	110.2
H4—N2—H5	108.2	C7—C6—H20	110.2
C5—N3—Co1	109.69 (16)	H19—C6—H20	108.5
C5—N3—H6	109.7	N5—C7—C6	108.1 (2)
Co1—N3—H6	109.7	N5—C7—H21	110.1
C5—N3—H7	109.7	C6—C7—H21	110.1
Co1—N3—H7	109.7	N5—C7—H22	110.1
H6—N3—H7	108.2	C6—C7—H22	110.1
C6—N4—Co1	108.40 (16)	H21—C7—H22	108.4
C6—N4—H8	110.0	O6—Cl1—O3	113.2 (2)
Co1—N4—H8	110.0	O6—Cl1—O5	108.9 (2)
C6—N4—H9	110.0	O3—Cl1—O5	110.90 (17)
Co1—N4—H9	110.0	O6—Cl1—O4	106.7 (3)
H8—N4—H9	108.4	O3—Cl1—O4	107.5 (2)
C7—N5—Co1	110.64 (17)	O5—Cl1—O4	109.6 (2)
C7—N5—H10	109.5	O10—Cl2—O9	110.5 (3)
Co1—N5—H10	109.5	O10—Cl2—O8	110.3 (4)
C7—N5—H11	109.5	O9—Cl2—O8	107.4 (3)
Co1—N5—H11	109.5	O10—Cl2—O7	111.8 (3)
H10—N5—H11	108.1	O9—Cl2—O7	107.9 (2)
C2—C1—S1	108.04 (17)	O8—Cl2—O7	108.8 (3)
C2—C1—H12	110.1	H23—O11—H24	121 (3)
S1—C1—H12	110.1
N2—Co1—S1—C1	−106.38 (12)	N3—Co1—N5—C7	101.1 (2)
N5—Co1—S1—C1	75.76 (12)	N1—Co1—N5—C7	−81.03 (19)
N3—Co1—S1—C1	168.40 (12)	N4—Co1—N5—C7	11.07 (19)
N1—Co1—S1—C1	−15.39 (12)	S1—Co1—N5—C7	−168.88 (18)
N2—Co1—N1—C2	79.22 (17)	Co1—S1—C1—C2	39.72 (19)
N5—Co1—N1—C2	−102.76 (17)	Co1—N1—C2—C1	39.7 (2)
N4—Co1—N1—C2	172.51 (16)	Co1—N1—C2—C3	165.85 (15)
S1—Co1—N1—C2	−10.70 (15)	S1—C1—C2—N1	−53.0 (2)
N3—Co1—N2—C4	16.44 (17)	S1—C1—C2—C3	−176.94 (16)
N1—Co1—N2—C4	−161.33 (17)	N1—C2—C3—O1	24.7 (3)
N4—Co1—N2—C4	106.40 (17)	C1—C2—C3—O1	148.2 (3)
S1—Co1—N2—C4	−73.52 (16)	N1—C2—C3—O2	−157.3 (2)
N2—Co1—N3—C5	11.85 (17)	C1—C2—C3—O2	−33.8 (3)
N5—Co1—N3—C5	−166.08 (18)	Co1—N2—C4—C5	−40.9 (2)
N4—Co1—N3—C5	−81.39 (18)	Co1—N3—C5—C4	−36.9 (2)
S1—Co1—N3—C5	101.81 (17)	N2—C4—C5—N3	50.3 (3)
N2—Co1—N4—C6	−161.58 (18)	Co1—N4—C6—C7	−39.8 (3)
N5—Co1—N4—C6	16.28 (18)	Co1—N5—C7—C6	−35.9 (3)
N3—Co1—N4—C6	−76.35 (18)	N4—C6—C7—N5	49.6 (3)
N1—Co1—N4—C6	107.31 (18)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
N2—H5···O1^i	0.90	2.13	2.906 (3)	144
O2—H1···O11	0.81 (2)	1.89 (3)	2.603 (3)	147 (5)
N1—H3···O3	0.90	2.20	3.042 (4)	156
N1—H2···O5^ii	0.90	2.25	3.013 (3)	143
N2—H5···O3	0.90	2.43	3.095 (4)	131
N2—H4···O7	0.90	2.30	3.141 (4)	155
N3—H7···O8^iii	0.90	2.67	3.307 (5)	128
N3—H6···O8^iv	0.90	2.61	3.379 (6)	144
N4—H9···O3	0.90	2.45	3.106 (3)	130
N5—H10···O5^ii	0.90	2.42	3.154 (4)	139
N5—H11···O6^v	0.90	2.32	3.106 (4)	147

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