Bis[N,N-diisobutyl-N′-(2-thienylcarbon­yl)thio­ureato]nickel(II)

Gomes, L.R.; Santos, L.M.N.B.F.; Schröder, B.; Wagner, C.; Low, J.N.

doi:10.1107/S1600536807009403

Bis[N,N-diisobutyl-N'-(2-thienylcarbonyl)thioureato]nickel(II)

L. R. Gomes, L. M. N. B. F. Santos, B. Schröder, C. Wagner and J. N. Low

In the title complex, [Ni(C₁₄H₂₁N₂OS₂)₂], the Ni^II ion is in a square-planar coordination enviroment. The ligands assume a cis arrangement with respect to each other around the Ni^II ion, which lies on a crystallographic twofold rotation axis running parallel to the c axis. The title complex is isostructural with the copper(II) analogue.

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Supporting information

	Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536807009403/lh2318sup1.cif Contains datablocks global, I
	Structure factor file (CIF format) https://doi.org/10.1107/S1600536807009403/lh2318Isup2.hkl Contains datablock I

CCDC reference: 600468

checkCIF report

Key indicators

Single-crystal X-ray study
T = 290 K
Mean (C-C) = 0.008 Å
Disorder in main residue
R factor = 0.038
wR factor = 0.099
Data-to-parameter ratio = 16.1

checkCIF/PLATON results

No syntax errors found



Alert level C
PLAT220_ALERT_2_C Large Non-Solvent    C     Ueq(max)/Ueq(min) ...       2.70 Ratio
PLAT241_ALERT_2_C Check High      Ueq as Compared to Neighbors for         C5
PLAT241_ALERT_2_C Check High      Ueq as Compared to Neighbors for         C7
PLAT241_ALERT_2_C Check High      Ueq as Compared to Neighbors for         C9
PLAT242_ALERT_2_C Check Low       Ueq as Compared to Neighbors for        C8A
PLAT242_ALERT_2_C Check Low       Ueq as Compared to Neighbors for        C8B
PLAT301_ALERT_3_C Main Residue  Disorder .........................       9.00 Perc.
PLAT341_ALERT_3_C Low Bond Precision on C-C bonds (x 1000) Ang ...          8
PLAT601_ALERT_2_C Structure Contains Solvent Accessible VOIDS of .      59.00 A   3 
PLAT720_ALERT_4_C Number of Unusual/Non-Standard Label(s) ........          1

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           26.00
           From the CIF: _reflns_number_total               2957
           Count of symmetry unique reflns         1770
           Completeness (_total/calc)            167.06%
           TEST3: Check Friedels for noncentro structure
           Estimate of Friedel pairs measured      1187
           Fraction of Friedel pairs measured     0.671
           Are heavy atom types Z>Si present        yes

   0 ALERT level A = In general: serious problem
   0 ALERT level B = Potentially serious problem
  10 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
   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
   2 ALERT type 4 Improvement, methodology, query or suggestion
   0 ALERT type 5 Informative message, check

Computing details top

Data collection: IPDS Software (Stoe & Cie, 1996); cell refinement: CELL (Burzlaff, 1996); data reduction: INTEGRATE in IPDS Software; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEPIII (Johnson & Burnett, 1998); software used to prepare material for publication: SHELXL97.

Bis[N,N-diisobutyl-N'-(2-thienylcarbonyl)thioureato]copper(II) top

Crystal data top

[Ni(C₁₄H₂₁N₂OS₂)₂]	D_x = 1.242 Mg m⁻³
M_r = 653.60	Mo Kα radiation, λ = 0.71073 Å
Tetragonal, I4	Cell parameters from 20 reflections
Hall symbol: I -4	θ = 2.1–26.8°
a = 13.077 (9) Å	µ = 0.82 mm⁻¹
c = 20.44 (2) Å	T = 290 K
V = 3495 (5) Å³	Prismatic, violet
Z = 4	0.3 × 0.2 × 0.1 mm
F(000) = 1384

Data collection top

Stoe Stadi-4 diffractometer	2785 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	R_int = 0.028
Graphite monochromator	θ_max = 26.0°, θ_min = 1.9°
Profile fitted 2θ/w scans (Clegg, 1981)	h = −16→10
Absorption correction: ψ scan (North et al., 1968)	k = −3→16
T_min = 0.790, T_max = 0.922	l = −25→0
3040 measured reflections	16 standard reflections every 60 min
2957 independent reflections	intensity decay: none

Refinement top

Refinement on F²	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F² > 2σ(F²)] = 0.038	H-atom parameters constrained
wR(F²) = 0.099	w = 1/[σ²(F_o²) + (0.05P)² + 3.1544P] where P = (F_o² + 2F_c²)/3
S = 1.08	(Δ/σ)_max = 0.001
2957 reflections	Δρ_max = 0.52 e Å⁻³
184 parameters	Δρ_min = −0.60 e Å⁻³
6 restraints	Absolute structure: Flack (1983), 1653 Friedel pairs
Primary atom site location: structure-invariant direct methods	Absolute structure parameter: 0.003 (15)

Special details top

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 (Å²) top

	x	y	z	U_iso*/U_eq	Occ. (<1)
Ni1	0.5000	0.5000	0.83692 (3)	0.04292 (16)
S1	0.39086 (15)	0.86168 (10)	0.96810 (7)	0.0893 (4)
C2	0.4370 (3)	0.7387 (3)	0.9649 (2)	0.0566 (9)
C3	0.4763 (4)	0.7095 (4)	1.0236 (2)	0.0702 (12)
H3	0.5038	0.6451	1.0317	0.084*
C4	0.4705 (5)	0.7871 (6)	1.0706 (3)	0.0946 (18)
H4	0.4941	0.7798	1.1133	0.114*
C5	0.4281 (6)	0.8721 (5)	1.0482 (3)	0.108 (2)
H5	0.4195	0.9310	1.0732	0.130*
C21	0.4295 (3)	0.6789 (3)	0.90372 (19)	0.0493 (8)
O2	0.4740 (2)	0.5933 (2)	0.90436 (12)	0.0567 (6)
N1	0.3746 (3)	0.7229 (2)	0.85731 (16)	0.0554 (8)
C6	0.3690 (3)	0.6891 (3)	0.79582 (19)	0.0502 (8)
S2	0.44967 (8)	0.59998 (8)	0.75955 (4)	0.0541 (2)
N2	0.2958 (3)	0.7322 (3)	0.75909 (17)	0.0590 (8)
C7	0.2884 (5)	0.7188 (5)	0.6879 (3)	0.0942 (12)
H7A	0.2207	0.7394	0.6737	0.113*	0.627 (12)
H7B	0.2965	0.6468	0.6776	0.113*	0.627 (12)
H7C	0.2195	0.6966	0.6775	0.113*	0.373 (12)
H7D	0.3346	0.6643	0.6751	0.113*	0.373 (12)
C8A	0.3676 (7)	0.7798 (7)	0.6496 (3)	0.085 (3)	0.627 (12)
H8A	0.4350	0.7482	0.6552	0.102*	0.627 (12)
C8B	0.3128 (9)	0.8129 (5)	0.6466 (3)	0.069 (4)	0.373 (12)
H8B	0.2580	0.8640	0.6474	0.082*	0.373 (12)
C9	0.3372 (5)	0.7753 (5)	0.5774 (2)	0.0942 (12)
H9A	0.3877	0.8100	0.5516	0.141*	0.313 (6)
H9B	0.2720	0.8079	0.5716	0.141*	0.313 (6)
H9C	0.3327	0.7052	0.5637	0.141*	0.313 (6)
H9D	0.2739	0.7387	0.5730	0.141*	0.313 (6)
H9E	0.3896	0.7409	0.5530	0.141*	0.313 (6)
H9F	0.3289	0.8435	0.5609	0.141*	0.313 (6)
H9G	0.3570	0.8323	0.5506	0.141*	0.187 (6)
H9H	0.2777	0.7433	0.5590	0.141*	0.187 (6)
H9I	0.3922	0.7267	0.5792	0.141*	0.187 (6)
H9J	0.3276	0.7026	0.5752	0.141*	0.187 (6)
H9K	0.4069	0.7916	0.5669	0.141*	0.187 (6)
H9LF	0.2924	0.8081	0.5467	0.141*	0.187 (6)
C10A	0.3738 (15)	0.8924 (6)	0.6675 (8)	0.133 (6)	0.627 (12)
H10A	0.3066	0.9218	0.6664	0.200*	0.313 (6)
H10B	0.4171	0.9273	0.6368	0.200*	0.313 (6)
H10C	0.4018	0.8993	0.7107	0.200*	0.313 (6)
H10D	0.4437	0.9105	0.6762	0.200*	0.313 (6)
H10E	0.3332	0.9050	0.7058	0.200*	0.313 (6)
H10F	0.3485	0.9330	0.6319	0.200*	0.313 (6)
C10B	0.4145 (11)	0.8545 (16)	0.6712 (10)	0.085 (3)	0.373 (12)
H10G	0.4669	0.8042	0.6647	0.128*	0.187 (6)
H10H	0.4090	0.8702	0.7169	0.128*	0.187 (6)
H10I	0.4316	0.9155	0.6474	0.128*	0.187 (6)
H10J	0.4047	0.9224	0.6880	0.128*	0.187 (6)
H10K	0.4627	0.8564	0.6358	0.128*	0.187 (6)
H10L	0.4401	0.8111	0.7053	0.128*	0.187 (6)
C11	0.2228 (3)	0.8022 (4)	0.7917 (2)	0.0717 (13)
H11A	0.1870	0.8413	0.7585	0.086*
H11B	0.2609	0.8500	0.8186	0.086*
C12	0.1449 (4)	0.7479 (5)	0.8341 (3)	0.0864 (15)
H12	0.1816	0.7004	0.8628	0.104*
C13	0.0687 (5)	0.6858 (6)	0.7928 (3)	0.111 (2)
H13A	0.1053	0.6469	0.7605	0.166*	0.50
H13B	0.0220	0.7315	0.7713	0.166*	0.50
H13C	0.0312	0.6401	0.8207	0.166*	0.50
H13D	0.0004	0.6988	0.8078	0.166*	0.50
H13E	0.0836	0.6142	0.7970	0.166*	0.50
H13F	0.0745	0.7056	0.7477	0.166*	0.50
C14	0.0887 (5)	0.8266 (6)	0.8776 (3)	0.110 (2)
H14A	0.0538	0.7915	0.9123	0.165*	0.50
H14B	0.0401	0.8636	0.8517	0.165*	0.50
H14C	0.1375	0.8734	0.8959	0.165*	0.50
H14D	0.1005	0.8942	0.8610	0.165*	0.50
H14E	0.1141	0.8220	0.9216	0.165*	0.50
H14F	0.0167	0.8123	0.8773	0.165*	0.50

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Ni1	0.0439 (3)	0.0385 (3)	0.0464 (3)	0.0053 (3)	0.000	0.000
S1	0.1229 (12)	0.0552 (7)	0.0898 (8)	0.0180 (7)	0.0172 (8)	−0.0150 (6)
C2	0.059 (2)	0.049 (2)	0.061 (2)	0.0040 (19)	0.0076 (19)	−0.0082 (18)
C3	0.069 (3)	0.080 (3)	0.062 (2)	0.011 (2)	−0.003 (2)	−0.010 (2)
C4	0.081 (4)	0.132 (5)	0.070 (3)	0.000 (4)	−0.002 (3)	−0.035 (3)
C5	0.127 (5)	0.095 (4)	0.103 (4)	−0.009 (4)	0.017 (4)	−0.051 (4)
C21	0.0480 (19)	0.0428 (18)	0.057 (2)	0.0008 (16)	0.0070 (16)	−0.0011 (15)
O2	0.0749 (17)	0.0443 (14)	0.0510 (13)	0.0140 (14)	−0.0019 (13)	−0.0007 (11)
N1	0.0592 (18)	0.0463 (16)	0.0607 (18)	0.0098 (15)	−0.0009 (15)	−0.0015 (14)
C6	0.0468 (18)	0.0417 (17)	0.062 (2)	0.0017 (15)	0.0012 (16)	0.0095 (16)
S2	0.0594 (5)	0.0526 (5)	0.0502 (5)	0.0129 (4)	0.0002 (4)	0.0040 (4)
N2	0.0529 (17)	0.0587 (18)	0.066 (2)	0.0100 (15)	−0.0007 (15)	0.0175 (16)
C7	0.107 (3)	0.107 (3)	0.069 (2)	−0.016 (3)	−0.008 (2)	0.016 (2)
C8A	0.089 (6)	0.086 (5)	0.081 (5)	−0.020 (5)	−0.015 (4)	0.033 (5)
C8B	0.072 (8)	0.069 (8)	0.064 (7)	0.021 (7)	−0.012 (6)	0.020 (6)
C9	0.107 (3)	0.107 (3)	0.069 (2)	−0.016 (3)	−0.008 (2)	0.016 (2)
C10A	0.206 (16)	0.067 (6)	0.127 (9)	−0.009 (9)	0.019 (12)	0.028 (7)
C10B	0.089 (6)	0.086 (5)	0.081 (5)	−0.020 (5)	−0.015 (4)	0.033 (5)
C11	0.058 (3)	0.070 (3)	0.087 (3)	0.031 (2)	−0.001 (2)	0.010 (2)
C12	0.067 (3)	0.102 (4)	0.090 (3)	0.033 (3)	0.003 (3)	0.024 (3)
C13	0.071 (4)	0.131 (6)	0.129 (5)	−0.004 (4)	0.010 (4)	−0.001 (5)
C14	0.086 (4)	0.152 (6)	0.092 (4)	0.037 (4)	0.017 (3)	0.008 (4)

Geometric parameters (Å, º) top

Ni1—O2ⁱ	1.872 (3)	C9—H9F	0.9600
Ni1—O2	1.872 (3)	C9—H9G	0.9600
Ni1—S2	2.1549 (17)	C9—H9H	0.9600
Ni1—S2ⁱ	2.1549 (17)	C9—H9I	0.9600
S1—C5	1.714 (7)	C9—H9J	0.9600
S1—C2	1.719 (4)	C9—H9K	0.9600
C2—C3	1.360 (6)	C9—H9LF	0.9600
C2—C21	1.478 (5)	C10A—H10A	0.9600
C3—C4	1.400 (7)	C10A—H10B	0.9600
C3—H3	0.9300	C10A—H10C	0.9600
C4—C5	1.324 (9)	C10A—H10D	0.9600
C4—H4	0.9300	C10A—H10E	0.9600
C5—H5	0.9300	C10A—H10F	0.9600
C21—O2	1.261 (5)	C10B—H10G	0.9600
C21—N1	1.321 (5)	C10B—H10H	0.9600
N1—C6	1.334 (5)	C10B—H10I	0.9600
C6—N2	1.341 (5)	C10B—H10J	0.9600
C6—S2	1.738 (4)	C10B—H10K	0.9600
N2—C7	1.470 (7)	C10B—H10L	0.9600
N2—C11	1.481 (5)	C11—C12	1.514 (7)
C7—C8A	1.523 (5)	C11—H11A	0.9700
C7—C8B	1.525 (5)	C11—H11B	0.9700
C7—H7A	0.9700	C12—C13	1.539 (9)
C7—H7B	0.9700	C12—C14	1.545 (8)
C7—H7C	0.9700	C12—H12	0.9800
C7—H7D	0.9700	C13—H13A	0.9600
C8A—C10A	1.521 (5)	C13—H13B	0.9600
C8A—C9	1.529 (5)	C13—H13C	0.9600
C8A—H8A	0.9800	C13—H13D	0.9600
C8B—C10B	1.523 (5)	C13—H13E	0.9600
C8B—C9	1.531 (5)	C13—H13F	0.9600
C8B—H8B	0.9800	C14—H14A	0.9600
C9—H9A	0.9600	C14—H14B	0.9600
C9—H9B	0.9600	C14—H14C	0.9600
C9—H9C	0.9600	C14—H14D	0.9600
C9—H9D	0.9600	C14—H14E	0.9600
C9—H9E	0.9600	C14—H14F	0.9600

O2ⁱ—Ni1—O2	85.19 (17)	H9I—C9—H9J	56.3
O2ⁱ—Ni1—S2	172.46 (10)	C8A—C9—H9K	87.7
O2—Ni1—S2	95.12 (10)	C8B—C9—H9K	109.5
O2ⁱ—Ni1—S2ⁱ	95.12 (10)	H9B—C9—H9K	135.8
O2—Ni1—S2ⁱ	172.46 (10)	H9C—C9—H9K	101.8
S2—Ni1—S2ⁱ	85.57 (9)	H9D—C9—H9K	155.2
C5—S1—C2	90.6 (3)	H9E—C9—H9K	46.4
C3—C2—C21	128.5 (4)	H9F—C9—H9K	79.8
C3—C2—S1	111.2 (3)	H9G—C9—H9K	56.3
C21—C2—S1	120.2 (3)	H9H—C9—H9K	141.1
C2—C3—C4	112.4 (5)	H9I—C9—H9K	56.3
C2—C3—H3	123.8	H9J—C9—H9K	109.5
C4—C3—H3	123.8	C8A—C9—H9LF	140.6
C5—C4—C3	113.2 (5)	C8B—C9—H9LF	109.5
C5—C4—H4	123.4	H9A—C9—H9LF	81.3
C3—C4—H4	123.4	H9C—C9—H9LF	101.5
C4—C5—S1	112.5 (4)	H9D—C9—H9LF	68.7
C4—C5—H5	123.8	H9E—C9—H9LF	107.8
S1—C5—H5	123.8	H9G—C9—H9LF	56.3
O2—C21—N1	130.1 (4)	H9H—C9—H9LF	56.3
O2—C21—C2	115.5 (3)	H9I—C9—H9LF	141.1
N1—C21—C2	114.4 (3)	H9J—C9—H9LF	109.5
C21—O2—Ni1	130.9 (2)	H9K—C9—H9LF	109.5
C21—N1—C6	124.2 (3)	C8A—C10A—H10A	109.5
N1—C6—N2	115.3 (3)	C8A—C10A—H10B	109.5
N1—C6—S2	126.2 (3)	H10A—C10A—H10B	109.5
N2—C6—S2	118.4 (3)	C8A—C10A—H10C	109.5
C6—S2—Ni1	106.22 (14)	H10A—C10A—H10C	109.5
C6—N2—C7	123.5 (4)	H10B—C10A—H10C	109.5
C6—N2—C11	117.9 (4)	C8A—C10A—H10D	109.5
C7—N2—C11	118.5 (4)	H10A—C10A—H10D	141.1
N2—C7—C8A	113.7 (5)	H10B—C10A—H10D	56.3
N2—C7—C8B	116.0 (5)	H10C—C10A—H10D	56.3
N2—C7—H7A	108.8	C8A—C10A—H10E	109.5
C8A—C7—H7A	108.8	H10A—C10A—H10E	56.3
C8B—C7—H7A	78.6	H10B—C10A—H10E	141.1
N2—C7—H7B	108.8	H10C—C10A—H10E	56.3
C8A—C7—H7B	108.8	H10D—C10A—H10E	109.5
C8B—C7—H7B	129.8	C8A—C10A—H10F	109.5
H7A—C7—H7B	107.7	H10A—C10A—H10F	56.3
N2—C7—H7C	108.3	H10B—C10A—H10F	56.3
C8A—C7—H7C	132.5	H10C—C10A—H10F	141.1
C8B—C7—H7C	108.3	H10D—C10A—H10F	109.5
H7B—C7—H7C	76.3	H10E—C10A—H10F	109.5
N2—C7—H7D	108.3	C8B—C10B—H10G	109.5
C8A—C7—H7D	79.8	C8B—C10B—H10H	109.5
C8B—C7—H7D	108.3	H10G—C10B—H10H	109.5
H7A—C7—H7D	133.8	C8B—C10B—H10I	109.5
H7C—C7—H7D	107.4	H10G—C10B—H10I	109.5
C10A—C8A—C7	114.8 (9)	H10H—C10B—H10I	109.5
C10A—C8A—C9	106.5 (9)	C8B—C10B—H10J	109.5
C7—C8A—C9	107.4 (5)	H10G—C10B—H10J	141.1
C10A—C8A—H8A	109.3	H10H—C10B—H10J	56.3
C7—C8A—H8A	109.3	H10I—C10B—H10J	56.3
C9—C8A—H8A	109.3	C8B—C10B—H10K	109.5
C10B—C8B—C7	106.7 (9)	H10G—C10B—H10K	56.3
C10B—C8B—C9	103.8 (11)	H10H—C10B—H10K	141.1
C7—C8B—C9	107.2 (5)	H10I—C10B—H10K	56.3
C10B—C8B—H8B	112.8	H10J—C10B—H10K	109.5
C7—C8B—H8B	112.8	C8B—C10B—H10L	109.5
C9—C8B—H8B	112.8	H10G—C10B—H10L	56.3
C8A—C9—H9A	109.5	H10H—C10B—H10L	56.3
C8B—C9—H9A	120.0	H10I—C10B—H10L	141.1
C8A—C9—H9B	109.5	H10J—C10B—H10L	109.5
C8B—C9—H9B	77.7	H10K—C10B—H10L	109.5
H9A—C9—H9B	109.5	N2—C11—C12	113.7 (4)
C8A—C9—H9C	109.5	N2—C11—H11A	108.8
C8B—C9—H9C	124.3	C12—C11—H11A	108.8
H9A—C9—H9C	109.5	N2—C11—H11B	108.8
H9B—C9—H9C	109.5	C12—C11—H11B	108.8
C8A—C9—H9D	109.5	H11A—C11—H11B	107.7
C8B—C9—H9D	93.8	C11—C12—C13	111.7 (5)
H9A—C9—H9D	141.1	C11—C12—C14	109.7 (5)
H9B—C9—H9D	56.3	C13—C12—C14	111.1 (4)
H9C—C9—H9D	56.3	C11—C12—H12	108.1
C8A—C9—H9E	109.5	C13—C12—H12	108.1
C8B—C9—H9E	141.2	C14—C12—H12	108.1
H9A—C9—H9E	56.3	C12—C13—H13A	109.5
H9B—C9—H9E	141.1	C12—C13—H13B	109.5
H9C—C9—H9E	56.3	H13A—C13—H13B	109.5
H9D—C9—H9E	109.5	C12—C13—H13C	109.5
C8A—C9—H9F	109.5	H13A—C13—H13C	109.5
C8B—C9—H9F	90.2	H13B—C13—H13C	109.5
H9A—C9—H9F	56.3	C12—C13—H13D	109.5
H9B—C9—H9F	56.3	H13A—C13—H13D	141.1
H9C—C9—H9F	141.1	H13B—C13—H13D	56.3
H9D—C9—H9F	109.5	H13C—C13—H13D	56.3
H9E—C9—H9F	109.5	C12—C13—H13E	109.5
C8A—C9—H9G	116.7	H13A—C13—H13E	56.3
C8B—C9—H9G	109.5	H13B—C13—H13E	141.1
H9B—C9—H9G	79.9	H13C—C13—H13E	56.3
H9C—C9—H9G	126.3	H13D—C13—H13E	109.5
H9D—C9—H9G	124.5	C12—C13—H13F	109.5
H9E—C9—H9G	82.8	H13A—C13—H13F	56.3
C8A—C9—H9H	127.3	H13B—C13—H13F	56.3
C8B—C9—H9H	109.5	H13C—C13—H13F	141.1
H9A—C9—H9H	123.2	H13D—C13—H13F	109.5
H9B—C9—H9H	55.0	H13E—C13—H13F	109.5
H9C—C9—H9H	54.6	C12—C14—H14A	109.5
H9E—C9—H9H	99.8	C12—C14—H14B	109.5
H9F—C9—H9H	100.1	H14A—C14—H14B	109.5
H9G—C9—H9H	109.5	C12—C14—H14C	109.5
C8A—C9—H9I	78.1	H14A—C14—H14C	109.5
C8B—C9—H9I	109.5	H14B—C14—H14C	109.5
H9A—C9—H9I	79.5	C12—C14—H14D	109.5
H9B—C9—H9I	164.4	H14A—C14—H14D	141.1
H9C—C9—H9I	54.9	H14B—C14—H14D	56.3
H9D—C9—H9I	108.6	H14C—C14—H14D	56.3
H9F—C9—H9I	135.4	C12—C14—H14E	109.5
H9G—C9—H9I	109.5	H14A—C14—H14E	56.3
H9H—C9—H9I	109.5	H14B—C14—H14E	141.1
C8A—C9—H9J	96.7	H14C—C14—H14E	56.3
C8B—C9—H9J	109.5	H14D—C14—H14E	109.5
H9A—C9—H9J	122.2	C12—C14—H14F	109.5
H9B—C9—H9J	108.5	H14A—C14—H14F	56.3
H9D—C9—H9J	52.4	H14B—C14—H14F	56.3
H9E—C9—H9J	66.7	H14C—C14—H14F	141.1
H9F—C9—H9J	152.8	H14D—C14—H14F	109.5
H9G—C9—H9J	141.1	H14E—C14—H14F	109.5
H9H—C9—H9J	56.3

C5—S1—C2—C3	1.2 (4)	S2—C6—N2—C7	−8.6 (5)
C5—S1—C2—C21	−179.5 (4)	N1—C6—N2—C11	−6.8 (5)
C21—C2—C3—C4	179.8 (4)	S2—C6—N2—C11	175.5 (3)
S1—C2—C3—C4	−1.0 (6)	C6—N2—C7—C8A	−74.8 (7)
C2—C3—C4—C5	0.2 (8)	C11—N2—C7—C8A	101.1 (7)
C3—C4—C5—S1	0.8 (8)	C6—N2—C7—C8B	−110.1 (8)
C2—S1—C5—C4	−1.2 (6)	C11—N2—C7—C8B	65.8 (8)
C3—C2—C21—O2	−7.3 (6)	N2—C7—C8A—C10A	−50.7 (13)
S1—C2—C21—O2	173.6 (3)	C8B—C7—C8A—C10A	50.9 (14)
C3—C2—C21—N1	170.9 (4)	N2—C7—C8A—C9	−168.9 (6)
S1—C2—C21—N1	−8.2 (5)	C8B—C7—C8A—C9	−67.3 (6)
N1—C21—O2—Ni1	11.0 (6)	N2—C7—C8B—C10B	50.0 (13)
C2—C21—O2—Ni1	−171.0 (3)	C8A—C7—C8B—C10B	−43.7 (13)
O2ⁱ—Ni1—O2—C21	−164.2 (4)	N2—C7—C8B—C9	160.7 (6)
S2—Ni1—O2—C21	8.2 (3)	C8A—C7—C8B—C9	67.0 (6)
O2—C21—N1—C6	−11.3 (7)	C10A—C8A—C9—C8B	−56.2 (12)
C2—C21—N1—C6	170.8 (4)	C7—C8A—C9—C8B	67.3 (6)
C21—N1—C6—N2	168.5 (4)	C10B—C8B—C9—C8A	45.8 (11)
C21—N1—C6—S2	−14.0 (6)	C7—C8B—C9—C8A	−66.9 (6)
N1—C6—S2—Ni1	29.8 (4)	C6—N2—C11—C12	−73.9 (5)
N2—C6—S2—Ni1	−152.8 (3)	C7—N2—C11—C12	110.0 (5)
O2—Ni1—S2—C6	−22.03 (17)	N2—C11—C12—C13	−69.1 (5)
S2ⁱ—Ni1—S2—C6	165.51 (15)	N2—C11—C12—C14	167.4 (4)
N1—C6—N2—C7	169.2 (4)

Symmetry code: (i) −x+1, −y+1, z.

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C3—H3···O2ⁱⁱ	0.93	2.35	3.204 (6)	153

Symmetry code: (ii) y, −x+1, −z+2.

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Bis[N,N-diisobutyl-N'-(2-thienylcarbon­yl)thio­ureato]nickel(II)

Supporting information

Key indicators

checkCIF/PLATON results

Bis[N,N-diisobutyl-N'-(2-thienylcarbonyl)thioureato]nickel(II)