Tris(N,N-diethyl­carbamato-κ²S,S′)arsenic(III)

In the title compound, [As{S₂CN(C₂H₅)₂}₃], the coordination environment of the As atom can be described as a distorted trigonal anti­prism.

Key indicators

• Single-crystal X-ray study
• T = 298 K
• Mean [sigma](C-C) = 0.006 Å
• R factor = 0.033
• wR factor = 0.088
• Data-to-parameter ratio = 18.3

checkCIF/PLATON results

No syntax errors found



Alert level C
PLAT062_ALERT_4_C Rescale T(min) & T(max) by .....................       0.94
PLAT322_ALERT_2_C Check Hybridisation of  As1    in Main Residue .          ?
PLAT764_ALERT_4_C Overcomplete CIF Bond List Detected (Rep/Expd) .       1.12 Ratio

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      0.942
            Tmax scaled      0.561 Tmin scaled      0.536

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

   0 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
   1 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
   2 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: SHELXS97 (Sheldrick, 1997a); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997a); molecular graphics: SHELXTL (Sheldrick, 1997b); software used to prepare material for publication: SHELXTL.

Tris(N,N-diethylcarbamato-κ²S,S')arsenic(III)

Crystal data

[As(C5H10NS2)3]	F(000) = 1080
Mr = 519.70	Dx = 1.424 Mg m^−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 4083 reflections
a = 15.868 (5) Å	θ = 2.6–26.5°
b = 8.389 (3) Å	µ = 1.92 mm^−1
c = 18.548 (6) Å	T = 298 K
β = 100.990 (4)°	Block, orange-red
V = 2423.9 (14) Å^3	0.33 × 0.31 × 0.30 mm
Z = 4

Data collection

Siemens SMART CCD diffractometer	4257 independent reflections
Radiation source: fine-focus sealed tube	3141 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.038
φ and ω scans	θmax = 25.0°, θmin = 1.3°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −18→18
Tmin = 0.569, Tmax = 0.596	k = −9→9
12134 measured reflections	l = −22→16

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)] = 0.033	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.088	H-atom parameters constrained
S = 1.01	w = 1/[σ^2(Fo^2) + (0.0397P)^2 + 1.0408P] where P = (Fo^2 + 2Fc^2)/3
4257 reflections	(Δ/σ)max = 0.002
232 parameters	Δρmax = 0.67 e Å^−3
0 restraints	Δρmin = −0.46 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
As1	0.25896 (2)	0.80445 (4)	0.878817 (18)	0.03740 (12)
N1	0.45510 (17)	0.4362 (3)	0.89791 (15)	0.0455 (7)
N2	0.03384 (17)	0.7385 (3)	0.70982 (14)	0.0389 (7)
N3	0.25087 (18)	1.0919 (3)	1.06807 (14)	0.0444 (7)
S1	0.29442 (6)	0.53203 (11)	0.88517 (5)	0.0472 (2)
S2	0.44218 (7)	0.75214 (13)	0.89367 (7)	0.0683 (3)
S3	0.11414 (5)	0.73081 (11)	0.84921 (5)	0.0407 (2)
S4	0.19631 (6)	0.83642 (13)	0.72657 (5)	0.0538 (3)
S5	0.25468 (6)	0.80706 (11)	1.00515 (5)	0.0447 (2)
S6	0.21377 (6)	1.10783 (11)	0.92238 (5)	0.0483 (2)
C1	0.4053 (2)	0.5643 (4)	0.89273 (18)	0.0423 (8)
C2	0.5487 (2)	0.4508 (5)	0.9053 (2)	0.0589 (11)
H2A	0.5761	0.3635	0.9352	0.071*
H2B	0.5673	0.5494	0.9308	0.071*
C3	0.5776 (3)	0.4496 (6)	0.8328 (2)	0.0773 (14)
H3A	0.5539	0.3583	0.8049	0.116*
H3B	0.6392	0.4445	0.8411	0.116*
H3C	0.5584	0.5450	0.8062	0.116*
C4	0.4210 (3)	0.2726 (5)	0.8998 (2)	0.0601 (11)
H4A	0.4650	0.2054	0.9281	0.072*
H4B	0.3726	0.2744	0.9247	0.072*
C5	0.3936 (3)	0.2026 (6)	0.8271 (3)	0.0891 (16)
H5A	0.3467	0.2634	0.8000	0.134*
H5B	0.3754	0.0947	0.8320	0.134*
H5C	0.4406	0.2037	0.8013	0.134*
C6	0.1087 (2)	0.7665 (4)	0.75464 (17)	0.0371 (8)
C7	0.0218 (2)	0.7745 (5)	0.63068 (18)	0.0552 (10)
H7A	0.0609	0.8591	0.6231	0.066*
H7B	−0.0363	0.8123	0.6135	0.066*
C8	0.0377 (3)	0.6305 (6)	0.5860 (2)	0.0725 (13)
H8A	0.0934	0.5873	0.6054	0.109*
H8B	0.0350	0.6615	0.5358	0.109*
H8C	−0.0053	0.5512	0.5884	0.109*
C9	−0.0411 (2)	0.6705 (4)	0.73433 (19)	0.0425 (9)
H9A	−0.0219	0.6126	0.7798	0.051*
H9B	−0.0689	0.5951	0.6978	0.051*
C10	−0.1058 (3)	0.7959 (5)	0.7466 (2)	0.0590 (11)
H10A	−0.0799	0.8663	0.7854	0.089*
H10B	−0.1548	0.7448	0.7600	0.089*
H10C	−0.1237	0.8560	0.7023	0.089*
C11	0.24018 (19)	1.0152 (4)	1.00431 (18)	0.0382 (8)
C12	0.2768 (2)	1.0100 (5)	1.13914 (19)	0.0536 (10)
H12A	0.2554	0.9015	1.1346	0.064*
H12B	0.2508	1.0636	1.1758	0.064*
C13	0.3729 (3)	1.0067 (6)	1.1649 (2)	0.0739 (13)
H13A	0.3989	0.9507	1.1296	0.111*
H13B	0.3865	0.9535	1.2114	0.111*
H13C	0.3944	1.1139	1.1699	0.111*
C14	0.2447 (3)	1.2667 (5)	1.0699 (2)	0.0686 (13)
H14A	0.2694	1.3107	1.0303	0.082*
H14B	0.2784	1.3050	1.1158	0.082*
C15	0.1545 (3)	1.3265 (6)	1.0628 (3)	0.0915 (17)
H15A	0.1225	1.3006	1.0149	0.137*
H15B	0.1552	1.4401	1.0693	0.137*
H15C	0.1280	1.2773	1.0996	0.137*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
As1	0.0320 (2)	0.0344 (2)	0.0434 (2)	0.00130 (15)	0.00117 (14)	−0.00345 (16)
N1	0.0361 (17)	0.0447 (19)	0.0539 (18)	0.0077 (14)	0.0046 (13)	0.0008 (14)
N2	0.0375 (16)	0.0363 (16)	0.0397 (16)	−0.0019 (13)	−0.0006 (12)	−0.0013 (13)
N3	0.0489 (18)	0.0426 (18)	0.0394 (17)	−0.0059 (14)	0.0025 (13)	−0.0090 (14)
S1	0.0322 (5)	0.0355 (5)	0.0724 (6)	0.0009 (4)	0.0062 (4)	−0.0049 (4)
S2	0.0450 (6)	0.0448 (6)	0.1148 (10)	−0.0076 (5)	0.0145 (6)	−0.0001 (6)
S3	0.0349 (5)	0.0449 (5)	0.0400 (5)	−0.0007 (4)	0.0015 (4)	−0.0013 (4)
S4	0.0431 (6)	0.0704 (7)	0.0493 (6)	−0.0112 (5)	0.0127 (4)	−0.0060 (5)
S5	0.0506 (6)	0.0373 (5)	0.0426 (5)	0.0026 (4)	−0.0005 (4)	0.0004 (4)
S6	0.0546 (6)	0.0394 (5)	0.0477 (5)	0.0030 (4)	0.0015 (4)	0.0029 (4)
C1	0.036 (2)	0.043 (2)	0.049 (2)	0.0037 (16)	0.0073 (15)	−0.0014 (17)
C2	0.033 (2)	0.070 (3)	0.070 (3)	0.010 (2)	0.0010 (18)	0.002 (2)
C3	0.057 (3)	0.095 (4)	0.085 (3)	−0.009 (3)	0.027 (2)	−0.010 (3)
C4	0.056 (3)	0.045 (2)	0.079 (3)	0.007 (2)	0.013 (2)	0.002 (2)
C5	0.099 (4)	0.072 (3)	0.102 (4)	−0.005 (3)	0.035 (3)	−0.010 (3)
C6	0.0354 (19)	0.0318 (18)	0.0424 (19)	0.0028 (15)	0.0031 (15)	−0.0044 (15)
C7	0.052 (2)	0.071 (3)	0.038 (2)	−0.010 (2)	−0.0034 (17)	0.0026 (19)
C8	0.059 (3)	0.104 (4)	0.054 (3)	0.000 (3)	0.011 (2)	−0.016 (3)
C9	0.041 (2)	0.036 (2)	0.046 (2)	−0.0096 (16)	−0.0036 (16)	0.0024 (16)
C10	0.051 (2)	0.054 (3)	0.072 (3)	0.003 (2)	0.013 (2)	−0.004 (2)
C11	0.0282 (18)	0.040 (2)	0.045 (2)	−0.0032 (15)	0.0036 (14)	−0.0011 (16)
C12	0.058 (2)	0.060 (3)	0.043 (2)	−0.004 (2)	0.0086 (17)	−0.0075 (19)
C13	0.061 (3)	0.089 (4)	0.063 (3)	−0.002 (2)	−0.009 (2)	−0.007 (2)
C14	0.093 (4)	0.046 (3)	0.062 (3)	−0.007 (2)	0.003 (2)	−0.018 (2)
C15	0.114 (5)	0.078 (4)	0.084 (3)	0.039 (3)	0.020 (3)	−0.015 (3)

Geometric parameters (Å, º)

As1—S3	2.3417 (12)	C4—H4B	0.9700
As1—S1	2.3513 (12)	C5—H5A	0.9600
As1—S5	2.3573 (12)	C5—H5B	0.9600
As1—S6	2.8047 (13)	C5—H5C	0.9600
As1—S4	2.8221 (13)	C7—C8	1.513 (5)
As1—S2	2.9009 (15)	C7—H7A	0.9700
N1—C1	1.326 (4)	C7—H7B	0.9700
N1—C2	1.470 (4)	C8—H8A	0.9600
N1—C4	1.478 (5)	C8—H8B	0.9600
N2—C6	1.334 (4)	C8—H8C	0.9600
N2—C9	1.466 (4)	C9—C10	1.518 (5)
N2—C7	1.475 (4)	C9—H9A	0.9700
N3—C11	1.328 (4)	C9—H9B	0.9700
N3—C14	1.471 (5)	C10—H10A	0.9600
N3—C12	1.474 (4)	C10—H10B	0.9600
S1—C1	1.759 (3)	C10—H10C	0.9600
S2—C1	1.680 (4)	C12—C13	1.508 (5)
S3—C6	1.765 (3)	C12—H12A	0.9700
S4—C6	1.681 (4)	C12—H12B	0.9700
S5—C11	1.761 (3)	C13—H13A	0.9600
S6—C11	1.687 (3)	C13—H13B	0.9600
C2—C3	1.501 (5)	C13—H13C	0.9600
C2—H2A	0.9700	C14—C15	1.499 (6)
C2—H2B	0.9700	C14—H14A	0.9700
C3—H3A	0.9600	C14—H14B	0.9700
C3—H3B	0.9600	C15—H15A	0.9600
C3—H3C	0.9600	C15—H15B	0.9600
C4—C5	1.459 (6)	C15—H15C	0.9600
C4—H4A	0.9700
S3—As1—S1	88.29 (4)	H5B—C5—H5C	109.5
S3—As1—S5	91.29 (3)	N2—C6—S4	124.0 (3)
S1—As1—S5	90.64 (3)	N2—C6—S3	117.3 (3)
S3—As1—S6	90.78 (3)	S4—C6—S3	118.70 (18)
S1—As1—S6	159.97 (4)	N2—C7—C8	112.2 (3)
S5—As1—S6	69.37 (3)	N2—C7—H7A	109.2
S3—As1—S4	69.37 (3)	C8—C7—H7A	109.2
S1—As1—S4	100.24 (3)	N2—C7—H7B	109.2
S5—As1—S4	157.28 (4)	C8—C7—H7B	109.2
S6—As1—S4	98.13 (3)	H7A—C7—H7B	107.9
S3—As1—S2	154.60 (4)	C7—C8—H8A	109.5
S1—As1—S2	67.81 (3)	C7—C8—H8B	109.5
S5—As1—S2	97.20 (4)	H8A—C8—H8B	109.5
S6—As1—S2	114.62 (3)	C7—C8—H8C	109.5
S4—As1—S2	105.36 (4)	H8A—C8—H8C	109.5
C1—N1—C2	121.1 (3)	H8B—C8—H8C	109.5
C1—N1—C4	122.6 (3)	N2—C9—C10	112.9 (3)
C2—N1—C4	116.3 (3)	N2—C9—H9A	109.0
C6—N2—C9	123.6 (3)	C10—C9—H9A	109.0
C6—N2—C7	121.0 (3)	N2—C9—H9B	109.0
C9—N2—C7	115.4 (3)	C10—C9—H9B	109.0
C11—N3—C14	120.4 (3)	H9A—C9—H9B	107.8
C11—N3—C12	122.5 (3)	C9—C10—H10A	109.5
C14—N3—C12	116.9 (3)	C9—C10—H10B	109.5
C1—S1—As1	94.63 (12)	H10A—C10—H10B	109.5
C1—S2—As1	78.48 (12)	C9—C10—H10C	109.5
C6—S3—As1	92.77 (11)	H10A—C10—H10C	109.5
C6—S4—As1	79.12 (11)	H10B—C10—H10C	109.5
C11—S5—As1	91.65 (11)	N3—C11—S6	123.2 (3)
C11—S6—As1	78.95 (12)	N3—C11—S5	118.5 (2)
N1—C1—S2	123.9 (3)	S6—C11—S5	118.32 (19)
N1—C1—S1	117.0 (3)	N3—C12—C13	112.6 (3)
S2—C1—S1	119.1 (2)	N3—C12—H12A	109.1
N1—C2—C3	113.1 (3)	C13—C12—H12A	109.1
N1—C2—H2A	109.0	N3—C12—H12B	109.1
C3—C2—H2A	109.0	C13—C12—H12B	109.1
N1—C2—H2B	109.0	H12A—C12—H12B	107.8
C3—C2—H2B	109.0	C12—C13—H13A	109.5
H2A—C2—H2B	107.8	C12—C13—H13B	109.5
C2—C3—H3A	109.5	H13A—C13—H13B	109.5
C2—C3—H3B	109.5	C12—C13—H13C	109.5
H3A—C3—H3B	109.5	H13A—C13—H13C	109.5
C2—C3—H3C	109.5	H13B—C13—H13C	109.5
H3A—C3—H3C	109.5	N3—C14—C15	113.5 (4)
H3B—C3—H3C	109.5	N3—C14—H14A	108.9
C5—C4—N1	113.5 (4)	C15—C14—H14A	108.9
C5—C4—H4A	108.9	N3—C14—H14B	108.9
N1—C4—H4A	108.9	C15—C14—H14B	108.9
C5—C4—H4B	108.9	H14A—C14—H14B	107.7
N1—C4—H4B	108.9	C14—C15—H15A	109.5
H4A—C4—H4B	107.7	C14—C15—H15B	109.5
C4—C5—H5A	109.5	H15A—C15—H15B	109.5
C4—C5—H5B	109.5	C14—C15—H15C	109.5
H5A—C5—H5B	109.5	H15A—C15—H15C	109.5
C4—C5—H5C	109.5	H15B—C15—H15C	109.5
H5A—C5—H5C	109.5