Crystal structures and Hirshfeld surface analysis of trans-bis­(thio­cyanato-κN)bis­{2,4,6-trimethyl-N-[(pyridin-2-yl)methyl­idene]aniline-κ²N,N′}manganese(II) and trans-bis­(thio­cyanato-κN)bis­{2,4,6-trimethyl-N-[(pyridin-2-yl)methyl­idene]aniline-κ²N,N′}nickel(II))

Each metal cation in the mol­ecular structures of [Mn(NCS)₂(PM-TMA)₂] (I) and [Ni(NCS)₂(PM-TMA)₂] (II) (PM-TMA is 2,4,6-trimethyl-N-[(pyridin-2-yl)methyl­idene]aniline) is situated on an inversion centre and is in a distorted octa­hedral coordination by six N atoms.

Key indicators

Structure: 1

• Single-crystal X-ray study
• T = 296 K
• Mean [sigma](C-C) = 0.004 Å
• R factor = 0.044
• wR factor = 0.100
• Data-to-parameter ratio = 16.3

Structure: 2

• Single-crystal X-ray study
• T = 296 K
• Mean [sigma](C-C) = 0.005 Å
• R factor = 0.053
• wR factor = 0.104
• Data-to-parameter ratio = 16.0

checkCIF/PLATON results

No syntax errors found



Datablock: 1


Alert level C
PLAT480_ALERT_4_C Long H...A H-Bond Reported H3       ..S1       .       3.16 Ang.
PLAT480_ALERT_4_C Long H...A H-Bond Reported H5       ..S1       .       3.00 Ang.
PLAT480_ALERT_4_C Long H...A H-Bond Reported H7       ..S1       .       3.07 Ang.
PLAT715_ALERT_1_C D-H     Unknown or Inconsistent Label ..........          . Check
PLAT906_ALERT_3_C Large K Value in the Analysis of Variance ......      2.934 Check
PLAT911_ALERT_3_C Missing FCF Refl Between Thmin & STh/L=    0.600         32 Report

Alert level G
PLAT154_ALERT_1_G The s.u.'s on the Cell Angles are Equal ..(Note)      0.002 Degree
PLAT794_ALERT_5_G Tentative Bond Valency for Mn1       (II)      .       2.02 Info
PLAT910_ALERT_3_G Missing # of FCF Reflection(s) Below Theta(Min).          4 Note
PLAT912_ALERT_4_G Missing # of FCF Reflections Above STh/L=  0.600         62 Note
PLAT978_ALERT_2_G Number C-C Bonds with Positive Residual Density.          7 Info

   0 ALERT level A = Most likely a serious problem - resolve or explain
   0 ALERT level B = A potentially serious problem, consider carefully
   6 ALERT level C = Check. Ensure it is not caused by an omission or oversight
   5 ALERT level G = General information/check it is not something unexpected

   2 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
   3 ALERT type 3 Indicator that the structure quality may be low
   4 ALERT type 4 Improvement, methodology, query or suggestion
   1 ALERT type 5 Informative message, check




Datablock: 2


Alert level C
PLAT480_ALERT_4_C Long H...A H-Bond Reported H4       ..S1       .       2.89 Ang.
PLAT480_ALERT_4_C Long H...A H-Bond Reported H10      ..S1       .       3.17 Ang.
PLAT911_ALERT_3_C Missing FCF Refl Between Thmin & STh/L=    0.600         19 Report

Alert level G
PLAT230_ALERT_2_G Hirshfeld Test Diff for    S1       --C1       .        5.4 s.u.
PLAT794_ALERT_5_G Tentative Bond Valency for Ni1       (II)      .       2.03 Info
PLAT910_ALERT_3_G Missing # of FCF Reflection(s) Below Theta(Min).          4 Note
PLAT912_ALERT_4_G Missing # of FCF Reflections Above STh/L=  0.600         13 Note
PLAT978_ALERT_2_G Number C-C Bonds with Positive Residual Density.          1 Info

   0 ALERT level A = Most likely a serious problem - resolve or explain
   0 ALERT level B = A potentially serious problem, consider carefully
   3 ALERT level C = Check. Ensure it is not caused by an omission or oversight
   5 ALERT level G = General information/check it is not something unexpected

   0 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
   2 ALERT type 3 Indicator that the structure quality may be low
   3 ALERT type 4 Improvement, methodology, query or suggestion
   1 ALERT type 5 Informative message, check

---

Computing details

For both structures, data collection: APEX3 (Bruker, 2016); cell refinement: SAINT (Bruker, 2016); data reduction: SAINT (Bruker, 2016); program(s) used to solve structure: ShelXT (Sheldrick, 2015a); program(s) used to refine structure: SHELXL (Sheldrick, 2015b); molecular graphics: OLEX2 (Dolomanov et al., 2009); software used to prepare material for publication: OLEX2 (Dolomanov et al., 2009).

trans-Bis(thiocyanato-κN)bis{2,4,6-trimethyl-N-[(pyridin-2-yl)methylidene]aniline-κ²N,N'}manganese(II) (1)

Crystal data

[Mn(NCS)2(C15H16N2)2]	Z = 1
Mr = 619.69	F(000) = 323
Triclinic, P1	Dx = 1.322 Mg m^−3
a = 8.5597 (5) Å	Mo Kα radiation, λ = 0.71073 Å
b = 9.0255 (5) Å	Cell parameters from 2271 reflections
c = 10.7718 (7) Å	θ = 2.9–25.8°
α = 91.718 (2)°	µ = 0.59 mm^−1
β = 109.830 (2)°	T = 296 K
γ = 95.080 (2)°	Block, yellow
V = 778.16 (8) Å^3	0.28 × 0.28 × 0.22 mm

Data collection

BRUKER D8 QUEST CMOS PHOTON II diffractometer	3091 independent reflections
Radiation source: sealed x-ray tube	2326 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.043
Detector resolution: 7.39 pixels mm^-1	θmax = 26.4°, θmin = 2.9°
φ and ω scans	h = −10→10
Absorption correction: multi-scan (SADABS; Krause et al., 2015)	k = −11→11
Tmin = 0.673, Tmax = 0.745	l = −13→13
7594 measured reflections

Refinement

Refinement on F^2	0 restraints
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F^2 > 2σ(F^2)] = 0.044	H-atom parameters constrained
wR(F^2) = 0.100	w = 1/[σ^2(Fo^2) + (0.0454P)^2 + 0.1287P] where P = (Fo^2 + 2Fc^2)/3
S = 1.02	(Δ/σ)max < 0.001
3091 reflections	Δρmax = 0.27 e Å^−3
190 parameters	Δρmin = −0.20 e Å^−3

Special details

Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Ų)

	x	y	z	Uiso*/Ueq
Mn1	0.500000	0.500000	0.500000	0.03059 (16)
S1	−0.00476 (8)	0.21358 (9)	0.19246 (7)	0.0556 (2)
N1	0.2655 (2)	0.3678 (2)	0.3908 (2)	0.0432 (5)
N2	0.3816 (2)	0.71929 (19)	0.47958 (17)	0.0305 (4)
N3	0.4064 (2)	0.5223 (2)	0.67669 (17)	0.0295 (4)
C1	0.1524 (3)	0.3041 (3)	0.3083 (2)	0.0352 (5)
C2	0.3662 (3)	0.8173 (3)	0.3873 (2)	0.0394 (6)
H2	0.403637	0.795727	0.317827	0.047*
C3	0.2972 (3)	0.9498 (3)	0.3898 (3)	0.0460 (6)
H3	0.286186	1.014330	0.322324	0.055*
C4	0.2457 (3)	0.9843 (3)	0.4924 (3)	0.0486 (7)
H4	0.200641	1.073625	0.496677	0.058*
C5	0.2609 (3)	0.8853 (3)	0.5905 (2)	0.0431 (6)
H5	0.226735	0.906801	0.661687	0.052*
C6	0.3284 (3)	0.7535 (2)	0.5801 (2)	0.0325 (5)
C7	0.3369 (3)	0.6414 (3)	0.6780 (2)	0.0340 (5)
H7	0.290036	0.657904	0.742805	0.041*
C8	0.3925 (3)	0.4146 (2)	0.7695 (2)	0.0301 (5)
C9	0.2353 (3)	0.3410 (3)	0.7554 (2)	0.0364 (5)
C10	0.2266 (3)	0.2367 (3)	0.8455 (2)	0.0415 (6)
H10	0.123433	0.186156	0.836340	0.050*
C11	0.3663 (3)	0.2049 (3)	0.9487 (2)	0.0403 (6)
C12	0.5191 (3)	0.2774 (3)	0.9573 (2)	0.0375 (6)
H12	0.614163	0.255307	1.024579	0.045*
C13	0.5366 (3)	0.3818 (2)	0.8697 (2)	0.0328 (5)
C14	0.0778 (3)	0.3699 (3)	0.6467 (3)	0.0531 (7)
H14A	0.041645	0.462049	0.667966	0.080*
H14B	−0.007793	0.289925	0.637957	0.080*
H14C	0.098935	0.376187	0.564940	0.080*
C15	0.3481 (4)	0.0982 (3)	1.0500 (3)	0.0573 (8)
H15A	0.456430	0.073952	1.103645	0.086*
H15B	0.280474	0.008835	1.005464	0.086*
H15C	0.295925	0.144197	1.105062	0.086*
C16	0.7065 (3)	0.4597 (3)	0.8867 (2)	0.0441 (6)
H16A	0.733250	0.440009	0.808518	0.066*
H16B	0.788622	0.423560	0.961442	0.066*
H16C	0.705757	0.565104	0.900840	0.066*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
Mn1	0.0319 (3)	0.0273 (3)	0.0335 (3)	0.0076 (2)	0.0113 (2)	0.0037 (2)
S1	0.0379 (4)	0.0659 (5)	0.0543 (4)	−0.0008 (3)	0.0070 (3)	−0.0082 (4)
N1	0.0384 (11)	0.0424 (13)	0.0473 (12)	0.0020 (10)	0.0131 (10)	0.0040 (10)
N2	0.0318 (10)	0.0278 (10)	0.0316 (10)	0.0050 (8)	0.0096 (8)	0.0048 (8)
N3	0.0300 (9)	0.0285 (10)	0.0294 (10)	0.0065 (8)	0.0084 (8)	0.0067 (8)
C1	0.0328 (12)	0.0352 (13)	0.0415 (14)	0.0094 (11)	0.0161 (11)	0.0071 (11)
C2	0.0447 (14)	0.0362 (14)	0.0399 (14)	0.0049 (11)	0.0170 (11)	0.0080 (11)
C3	0.0515 (15)	0.0363 (14)	0.0521 (16)	0.0106 (12)	0.0177 (13)	0.0171 (12)
C4	0.0556 (16)	0.0325 (14)	0.0646 (18)	0.0183 (12)	0.0251 (14)	0.0150 (12)
C5	0.0514 (15)	0.0372 (14)	0.0469 (15)	0.0149 (12)	0.0223 (12)	0.0058 (11)
C6	0.0329 (12)	0.0285 (12)	0.0348 (13)	0.0062 (10)	0.0091 (10)	0.0043 (10)
C7	0.0373 (12)	0.0367 (14)	0.0290 (12)	0.0084 (11)	0.0115 (10)	0.0022 (10)
C8	0.0360 (12)	0.0274 (12)	0.0291 (12)	0.0082 (10)	0.0126 (10)	0.0046 (9)
C9	0.0372 (12)	0.0377 (14)	0.0358 (13)	0.0097 (11)	0.0129 (10)	0.0060 (10)
C10	0.0425 (14)	0.0372 (14)	0.0498 (15)	0.0043 (11)	0.0220 (12)	0.0078 (12)
C11	0.0583 (16)	0.0299 (13)	0.0399 (14)	0.0116 (12)	0.0240 (12)	0.0072 (10)
C12	0.0465 (14)	0.0355 (13)	0.0299 (12)	0.0156 (12)	0.0095 (11)	0.0063 (10)
C13	0.0390 (12)	0.0299 (12)	0.0288 (12)	0.0088 (10)	0.0096 (10)	0.0015 (9)
C14	0.0353 (13)	0.0594 (18)	0.0598 (18)	0.0039 (13)	0.0092 (13)	0.0166 (14)
C15	0.078 (2)	0.0481 (17)	0.0577 (18)	0.0182 (15)	0.0347 (16)	0.0215 (14)
C16	0.0401 (13)	0.0474 (16)	0.0401 (14)	0.0053 (12)	0.0071 (11)	0.0077 (12)

Geometric parameters (Å, º)

Mn1—N1^i	2.174 (2)	C7—H7	0.9300
Mn1—N1	2.174 (2)	C8—C9	1.404 (3)
Mn1—N2^i	2.2856 (17)	C8—C13	1.398 (3)
Mn1—N2	2.2855 (17)	C9—C10	1.388 (3)
Mn1—N3	2.3118 (17)	C9—C14	1.505 (3)
Mn1—N3^i	2.3117 (17)	C10—H10	0.9300
S1—C1	1.624 (3)	C10—C11	1.387 (3)
N1—C1	1.160 (3)	C11—C12	1.382 (3)
N2—C2	1.332 (3)	C11—C15	1.514 (3)
N2—C6	1.346 (3)	C12—H12	0.9300
N3—C7	1.276 (3)	C12—C13	1.387 (3)
N3—C8	1.441 (3)	C13—C16	1.508 (3)
C2—H2	0.9300	C14—H14A	0.9600
C2—C3	1.383 (3)	C14—H14B	0.9600
C3—H3	0.9300	C14—H14C	0.9600
C3—C4	1.359 (4)	C15—H15A	0.9600
C4—H4	0.9300	C15—H15B	0.9600
C4—C5	1.384 (3)	C15—H15C	0.9600
C5—H5	0.9300	C16—H16A	0.9600
C5—C6	1.386 (3)	C16—H16B	0.9600
C6—C7	1.471 (3)	C16—H16C	0.9600
N1^i—Mn1—N1	180.0	N3—C7—H7	119.0
N1—Mn1—N2	93.63 (7)	C6—C7—H7	119.0
N1—Mn1—N2^i	86.37 (7)	C9—C8—N3	119.49 (19)
N1^i—Mn1—N2	86.37 (7)	C13—C8—N3	119.39 (19)
N1^i—Mn1—N2^i	93.63 (7)	C13—C8—C9	121.1 (2)
N1—Mn1—N3^i	91.50 (7)	C8—C9—C14	122.8 (2)
N1—Mn1—N3	88.50 (7)	C10—C9—C8	118.0 (2)
N1^i—Mn1—N3	91.50 (7)	C10—C9—C14	119.2 (2)
N1^i—Mn1—N3^i	88.50 (7)	C9—C10—H10	118.8
N2—Mn1—N2^i	180.0	C11—C10—C9	122.4 (2)
N2^i—Mn1—N3^i	74.26 (6)	C11—C10—H10	118.8
N2^i—Mn1—N3	105.74 (6)	C10—C11—C15	120.3 (2)
N2—Mn1—N3	74.26 (6)	C12—C11—C10	117.7 (2)
N2—Mn1—N3^i	105.74 (6)	C12—C11—C15	122.0 (2)
N3^i—Mn1—N3	180.00 (7)	C11—C12—H12	118.6
C1—N1—Mn1	164.27 (19)	C11—C12—C13	122.8 (2)
C2—N2—Mn1	129.08 (15)	C13—C12—H12	118.6
C2—N2—C6	117.55 (19)	C8—C13—C16	121.9 (2)
C6—N2—Mn1	113.30 (14)	C12—C13—C8	118.0 (2)
C7—N3—Mn1	112.59 (15)	C12—C13—C16	120.1 (2)
C7—N3—C8	116.82 (19)	C9—C14—H14A	109.5
C8—N3—Mn1	129.81 (13)	C9—C14—H14B	109.5
N1—C1—S1	179.4 (2)	C9—C14—H14C	109.5
N2—C2—H2	118.5	H14A—C14—H14B	109.5
N2—C2—C3	123.1 (2)	H14A—C14—H14C	109.5
C3—C2—H2	118.5	H14B—C14—H14C	109.5
C2—C3—H3	120.5	C11—C15—H15A	109.5
C4—C3—C2	119.0 (2)	C11—C15—H15B	109.5
C4—C3—H3	120.5	C11—C15—H15C	109.5
C3—C4—H4	120.3	H15A—C15—H15B	109.5
C3—C4—C5	119.4 (2)	H15A—C15—H15C	109.5
C5—C4—H4	120.3	H15B—C15—H15C	109.5
C4—C5—H5	120.8	C13—C16—H16A	109.5
C4—C5—C6	118.4 (2)	C13—C16—H16B	109.5
C6—C5—H5	120.8	C13—C16—H16C	109.5
N2—C6—C5	122.6 (2)	H16A—C16—H16B	109.5
N2—C6—C7	117.45 (19)	H16A—C16—H16C	109.5
C5—C6—C7	119.9 (2)	H16B—C16—H16C	109.5
N3—C7—C6	122.1 (2)
Mn1—N2—C2—C3	−177.25 (17)	C5—C6—C7—N3	−175.9 (2)
Mn1—N2—C6—C5	176.51 (18)	C6—N2—C2—C3	−0.8 (3)
Mn1—N2—C6—C7	−6.3 (2)	C7—N3—C8—C9	66.4 (3)
Mn1—N3—C7—C6	−3.2 (3)	C7—N3—C8—C13	−115.6 (2)
Mn1—N3—C8—C9	−102.6 (2)	C8—N3—C7—C6	−174.13 (19)
Mn1—N3—C8—C13	75.4 (2)	C8—C9—C10—C11	0.9 (4)
N2—C2—C3—C4	1.6 (4)	C9—C8—C13—C12	−1.9 (3)
N2—C6—C7—N3	6.8 (3)	C9—C8—C13—C16	−179.9 (2)
N3—C8—C9—C10	179.25 (19)	C9—C10—C11—C12	−2.3 (4)
N3—C8—C9—C14	−0.3 (3)	C9—C10—C11—C15	175.6 (2)
N3—C8—C13—C12	−179.89 (19)	C10—C11—C12—C13	1.7 (4)
N3—C8—C13—C16	2.1 (3)	C11—C12—C13—C8	0.4 (3)
C2—N2—C6—C5	−0.5 (3)	C11—C12—C13—C16	178.4 (2)
C2—N2—C6—C7	176.70 (19)	C13—C8—C9—C10	1.2 (3)
C2—C3—C4—C5	−1.0 (4)	C13—C8—C9—C14	−178.3 (2)
C3—C4—C5—C6	−0.1 (4)	C14—C9—C10—C11	−179.5 (2)
C4—C5—C6—N2	1.0 (4)	C15—C11—C12—C13	−176.3 (2)
C4—C5—C6—C7	−176.2 (2)

Symmetry code: (i) −x+1, −y+1, −z+1.

Hydrogen-bond geometry (Å, º)

Cg1 is the mid-point of the C1═N1 group. Cg2 and Cg3 are the centroids of the N2/C2–C6 and C8–C13 rings.

D—H···A	D—H	H···A	D···A	D—H···A
C3—H3···S1^ii	0.93	3.16	3.812 (3)	129
C4—H4···Cg1^ii	0.93	2.89	3.561 (3)	129
C5—H5···S1^iii	0.93	3.00	3.785 (3)	143
C7—H7···S1^iii	0.93	3.07	3.871 (2)	146
C14—H14A···Cg1^iii	0.96	2.89	3.779 (3)	153
C14—H14B···Cg2^iii	0.96	2.68	3.556 (3)	152
C16—H16C···Cg3^iv	0.96	3.14	3.711 (3)	145

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

trans-Bis(thiocyanato-κN)bis{2,4,6-trimethyl-N-[(pyridin-2-yl)methylidene]aniline-κ²N,N'}nickel(II) (2)

Crystal data

[Ni(NCS)2(C15H16N2)2]	F(000) = 652
Mr = 623.46	Dx = 1.333 Mg m^−3
Monoclinic, P21/n	Mo Kα radiation, λ = 0.71073 Å
a = 9.6156 (5) Å	Cell parameters from 9899 reflections
b = 12.6786 (7) Å	θ = 2.9–26.0°
c = 12.9870 (7) Å	µ = 0.79 mm^−1
β = 101.250 (2)°	T = 296 K
V = 1552.85 (14) Å^3	Block, yellow
Z = 2	0.34 × 0.3 × 0.3 mm

Data collection

BRUKER D8 QUEST CMOS PHOTON II diffractometer	3037 independent reflections
Radiation source: sealed x-ray tube	2486 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.032
Detector resolution: 7.39 pixels mm^-1	θmax = 26.1°, θmin = 2.9°
φ and ω scans	h = −11→11
Absorption correction: multi-scan (SADABS; Krause et al., 2015)	k = −15→15
Tmin = 0.607, Tmax = 0.745	l = −16→15
16977 measured reflections

Refinement

Refinement on F^2	Primary atom site location: dual
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F^2 > 2σ(F^2)] = 0.053	H-atom parameters constrained
wR(F^2) = 0.104	w = 1/[σ^2(Fo^2) + 2.7087P] where P = (Fo^2 + 2Fc^2)/3
S = 1.21	(Δ/σ)max < 0.001
3037 reflections	Δρmax = 0.70 e Å^−3
190 parameters	Δρmin = −0.46 e Å^−3
0 restraints

Special details

Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Ų)

	x	y	z	Uiso*/Ueq
Ni1	0.500000	0.500000	0.500000	0.03174 (15)
S1	0.30833 (12)	0.80667 (8)	0.64005 (9)	0.0656 (3)
N1	0.4244 (3)	0.6312 (2)	0.5593 (2)	0.0407 (6)
N2	0.7069 (3)	0.5629 (2)	0.5334 (2)	0.0376 (6)
N3	0.5103 (3)	0.58125 (19)	0.35336 (19)	0.0351 (6)
C1	0.3753 (3)	0.7033 (3)	0.5927 (2)	0.0380 (7)
C2	0.8053 (4)	0.5554 (3)	0.6204 (3)	0.0533 (9)
H2	0.783080	0.519973	0.677802	0.064*
C3	0.9390 (4)	0.5978 (4)	0.6293 (3)	0.0729 (13)
H3	1.005516	0.590034	0.691205	0.087*
C4	0.9733 (4)	0.6514 (4)	0.5467 (4)	0.0819 (15)
H4	1.062568	0.681377	0.551611	0.098*
C5	0.8729 (4)	0.6600 (4)	0.4559 (3)	0.0678 (12)
H5	0.893397	0.695433	0.398017	0.081*
C6	0.7414 (3)	0.6153 (3)	0.4521 (3)	0.0437 (8)
C7	0.6315 (3)	0.6226 (3)	0.3574 (3)	0.0444 (8)
H7	0.650545	0.658144	0.299091	0.053*
C8	0.4138 (3)	0.5878 (2)	0.2529 (2)	0.0372 (7)
C9	0.3021 (4)	0.6589 (3)	0.2392 (3)	0.0462 (8)
C10	0.2091 (4)	0.6604 (3)	0.1422 (3)	0.0545 (9)
H10	0.134814	0.708629	0.131543	0.065*
C11	0.2232 (4)	0.5933 (3)	0.0619 (3)	0.0517 (9)
C12	0.3352 (4)	0.5232 (3)	0.0780 (3)	0.0538 (9)
H12	0.345521	0.477030	0.024406	0.065*
C13	0.4330 (4)	0.5197 (3)	0.1723 (3)	0.0451 (8)
C14	0.2780 (5)	0.7328 (4)	0.3238 (3)	0.0732 (13)
H14A	0.250055	0.693336	0.379517	0.110*
H14B	0.204558	0.781995	0.295563	0.110*
H14C	0.364035	0.770498	0.350751	0.110*
C15	0.1202 (5)	0.5975 (4)	−0.0417 (3)	0.0734 (12)
H15A	0.029627	0.621583	−0.030483	0.110*
H15B	0.110203	0.528411	−0.072451	0.110*
H15C	0.155037	0.645291	−0.088141	0.110*
C16	0.5547 (5)	0.4432 (3)	0.1826 (3)	0.0675 (12)
H16A	0.642709	0.480996	0.199615	0.101*
H16B	0.550087	0.406302	0.117462	0.101*
H16C	0.548991	0.393416	0.237354	0.101*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
Ni1	0.0322 (3)	0.0306 (3)	0.0340 (3)	−0.0017 (2)	0.0105 (2)	−0.0011 (2)
S1	0.0730 (7)	0.0543 (6)	0.0761 (7)	0.0125 (5)	0.0307 (6)	−0.0150 (5)
N1	0.0474 (15)	0.0369 (15)	0.0401 (15)	0.0012 (12)	0.0139 (12)	−0.0028 (12)
N2	0.0351 (13)	0.0347 (14)	0.0434 (15)	−0.0050 (11)	0.0087 (11)	−0.0019 (11)
N3	0.0400 (14)	0.0316 (13)	0.0355 (13)	0.0054 (11)	0.0117 (11)	0.0039 (11)
C1	0.0377 (16)	0.0437 (19)	0.0340 (16)	−0.0035 (14)	0.0105 (13)	0.0018 (14)
C2	0.048 (2)	0.062 (2)	0.047 (2)	−0.0088 (18)	0.0038 (16)	−0.0006 (18)
C3	0.046 (2)	0.102 (4)	0.064 (3)	−0.016 (2)	−0.0051 (19)	−0.004 (3)
C4	0.043 (2)	0.112 (4)	0.089 (3)	−0.030 (2)	0.008 (2)	0.005 (3)
C5	0.050 (2)	0.083 (3)	0.073 (3)	−0.023 (2)	0.017 (2)	0.011 (2)
C6	0.0392 (17)	0.0463 (19)	0.0479 (19)	−0.0060 (15)	0.0142 (15)	0.0020 (15)
C7	0.0480 (19)	0.0442 (19)	0.0441 (18)	−0.0028 (15)	0.0169 (15)	0.0078 (15)
C8	0.0398 (16)	0.0388 (17)	0.0338 (16)	0.0008 (13)	0.0093 (13)	0.0053 (13)
C9	0.0468 (19)	0.047 (2)	0.0453 (19)	0.0090 (16)	0.0105 (15)	0.0071 (16)
C10	0.049 (2)	0.057 (2)	0.057 (2)	0.0144 (17)	0.0078 (17)	0.0106 (18)
C11	0.056 (2)	0.050 (2)	0.046 (2)	−0.0018 (17)	0.0022 (16)	0.0097 (17)
C12	0.072 (2)	0.050 (2)	0.0376 (18)	0.0048 (18)	0.0062 (17)	0.0020 (15)
C13	0.056 (2)	0.0425 (19)	0.0383 (17)	0.0090 (15)	0.0121 (15)	0.0079 (14)
C14	0.085 (3)	0.073 (3)	0.059 (2)	0.033 (2)	0.008 (2)	−0.006 (2)
C15	0.073 (3)	0.078 (3)	0.061 (3)	0.002 (2)	−0.008 (2)	0.007 (2)
C16	0.089 (3)	0.072 (3)	0.043 (2)	0.036 (2)	0.016 (2)	0.0029 (19)

Geometric parameters (Å, º)

Ni1—N1	2.027 (3)	C7—H7	0.9300
Ni1—N1^i	2.027 (3)	C8—C9	1.387 (4)
Ni1—N2^i	2.108 (2)	C8—C13	1.398 (4)
Ni1—N2	2.108 (2)	C9—C10	1.395 (5)
Ni1—N3	2.184 (2)	C9—C14	1.496 (5)
Ni1—N3^i	2.184 (2)	C10—H10	0.9300
S1—C1	1.632 (3)	C10—C11	1.373 (5)
N1—C1	1.152 (4)	C11—C12	1.380 (5)
N2—C2	1.329 (4)	C11—C15	1.508 (5)
N2—C6	1.343 (4)	C12—H12	0.9300
N3—C7	1.269 (4)	C12—C13	1.391 (5)
N3—C8	1.448 (4)	C13—C16	1.506 (5)
C2—H2	0.9300	C14—H14A	0.9600
C2—C3	1.378 (5)	C14—H14B	0.9600
C3—H3	0.9300	C14—H14C	0.9600
C3—C4	1.363 (6)	C15—H15A	0.9600
C4—H4	0.9300	C15—H15B	0.9600
C4—C5	1.374 (6)	C15—H15C	0.9600
C5—H5	0.9300	C16—H16A	0.9600
C5—C6	1.377 (5)	C16—H16B	0.9600
C6—C7	1.459 (5)	C16—H16C	0.9600
N1—Ni1—N1^i	180.00 (14)	N3—C7—H7	119.4
N1^i—Ni1—N2	89.71 (10)	C6—C7—H7	119.4
N1^i—Ni1—N2^i	90.29 (10)	C9—C8—N3	119.8 (3)
N1—Ni1—N2	90.29 (10)	C9—C8—C13	121.2 (3)
N1—Ni1—N2^i	89.71 (10)	C13—C8—N3	118.9 (3)
N1^i—Ni1—N3^i	91.41 (10)	C8—C9—C10	117.9 (3)
N1^i—Ni1—N3	88.59 (10)	C8—C9—C14	122.6 (3)
N1—Ni1—N3	91.41 (10)	C10—C9—C14	119.4 (3)
N1—Ni1—N3^i	88.59 (10)	C9—C10—H10	118.8
N2—Ni1—N2^i	180.0	C11—C10—C9	122.5 (3)
N2^i—Ni1—N3^i	78.43 (10)	C11—C10—H10	118.8
N2^i—Ni1—N3	101.57 (10)	C10—C11—C12	118.2 (3)
N2—Ni1—N3	78.43 (10)	C10—C11—C15	120.7 (4)
N2—Ni1—N3^i	101.57 (10)	C12—C11—C15	121.1 (4)
N3^i—Ni1—N3	180.00 (13)	C11—C12—H12	119.1
C1—N1—Ni1	176.7 (3)	C11—C12—C13	121.9 (3)
C2—N2—Ni1	129.4 (2)	C13—C12—H12	119.1
C2—N2—C6	117.4 (3)	C8—C13—C16	123.1 (3)
C6—N2—Ni1	113.2 (2)	C12—C13—C8	118.3 (3)
C7—N3—Ni1	110.9 (2)	C12—C13—C16	118.7 (3)
C7—N3—C8	115.8 (3)	C9—C14—H14A	109.5
C8—N3—Ni1	133.02 (19)	C9—C14—H14B	109.5
N1—C1—S1	179.0 (3)	C9—C14—H14C	109.5
N2—C2—H2	118.6	H14A—C14—H14B	109.5
N2—C2—C3	122.8 (4)	H14A—C14—H14C	109.5
C3—C2—H2	118.6	H14B—C14—H14C	109.5
C2—C3—H3	120.2	C11—C15—H15A	109.5
C4—C3—C2	119.6 (4)	C11—C15—H15B	109.5
C4—C3—H3	120.2	C11—C15—H15C	109.5
C3—C4—H4	120.7	H15A—C15—H15B	109.5
C3—C4—C5	118.5 (4)	H15A—C15—H15C	109.5
C5—C4—H4	120.7	H15B—C15—H15C	109.5
C4—C5—H5	120.5	C13—C16—H16A	109.5
C4—C5—C6	119.0 (4)	C13—C16—H16B	109.5
C6—C5—H5	120.5	C13—C16—H16C	109.5
N2—C6—C5	122.7 (3)	H16A—C16—H16B	109.5
N2—C6—C7	116.4 (3)	H16A—C16—H16C	109.5
C5—C6—C7	120.9 (3)	H16B—C16—H16C	109.5
N3—C7—C6	121.1 (3)
Ni1—N2—C2—C3	177.4 (3)	C5—C6—C7—N3	179.8 (4)
Ni1—N2—C6—C5	−178.0 (3)	C6—N2—C2—C3	−0.6 (6)
Ni1—N2—C6—C7	1.7 (4)	C7—N3—C8—C9	−105.0 (3)
Ni1—N3—C7—C6	−1.6 (4)	C7—N3—C8—C13	76.9 (4)
Ni1—N3—C8—C9	82.2 (4)	C8—N3—C7—C6	−176.0 (3)
Ni1—N3—C8—C13	−96.0 (3)	C8—C9—C10—C11	1.2 (5)
N2—C2—C3—C4	0.9 (7)	C9—C8—C13—C12	−1.4 (5)
N2—C6—C7—N3	0.0 (5)	C9—C8—C13—C16	178.4 (3)
N3—C8—C9—C10	−178.1 (3)	C9—C10—C11—C12	−1.0 (6)
N3—C8—C9—C14	1.7 (5)	C9—C10—C11—C15	179.9 (4)
N3—C8—C13—C12	176.8 (3)	C10—C11—C12—C13	−0.4 (6)
N3—C8—C13—C16	−3.5 (5)	C11—C12—C13—C8	1.6 (5)
C2—N2—C6—C5	0.3 (5)	C11—C12—C13—C16	−178.2 (4)
C2—N2—C6—C7	−179.9 (3)	C13—C8—C9—C10	0.0 (5)
C2—C3—C4—C5	−0.9 (8)	C13—C8—C9—C14	179.8 (4)
C3—C4—C5—C6	0.6 (8)	C14—C9—C10—C11	−178.6 (4)
C4—C5—C6—N2	−0.3 (7)	C15—C11—C12—C13	178.6 (4)
C4—C5—C6—C7	179.9 (4)

Symmetry code: (i) −x+1, −y+1, −z+1.

Hydrogen-bond geometry (Å, º)

Cg1 is the mid-point of the C1═N1 group.

D—H···A	D—H	H···A	D···A	D—H···A
C4—H4···S1^ii	0.93	2.89	3.769 (4)	158
C7—H7···S1^iii	0.93	2.83	3.680 (3)	153
C10—H10···S1^iv	0.93	3.17	3.871 (4)	134
C10—H10···Cg1^iv	0.93	2.73	3.655 (4)	171

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