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In the title compound, [Ni(C12H18N2S)2](C24H20B)2, the NiII atom is coordinated by two ligands via the thiol­ate S and the imine N atoms. The amine N atoms are protonated and inter­act with the phenyl rings of the BPh4 anions.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S2414314617010677/bv4008sup1.cif
Contains datablock I

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S2414314617010677/bv4008Isup2.hkl
Contains datablock I

CCDC reference: 1563052

checkCIF/PLATON results

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Datablock: I


Alert level B PLAT910_ALERT_3_B Missing # of FCF Reflection(s) Below Theta(Min) 11 Note
Alert level C PLAT420_ALERT_2_C D-H Without Acceptor N2 -- H2 ... Please Check PLAT906_ALERT_3_C Large K value in the Analysis of Variance ...... 5.109 Check PLAT911_ALERT_3_C Missing # FCF Refl Between THmin & STh/L= 0.600 27 Report
Alert level G PLAT007_ALERT_5_G Number of Unrefined Donor-H Atoms .............. 1 Report PLAT063_ALERT_4_G Crystal Size Likely too Large for Beam Size .... 0.63 mm PLAT083_ALERT_2_G SHELXL Second Parameter in WGHT Unusually Large 11.64 Why ? PLAT912_ALERT_4_G Missing # of FCF Reflections Above STh/L= 0.600 85 Note PLAT933_ALERT_2_G Number of OMIT Records in Embedded .res File ... 13 Note PLAT978_ALERT_2_G Number C-C Bonds with Positive Residual Density. 2 Note
0 ALERT level A = Most likely a serious problem - resolve or explain 1 ALERT level B = A potentially serious problem, consider carefully 3 ALERT level C = Check. Ensure it is not caused by an omission or oversight 6 ALERT level G = General information/check it is not something unexpected 0 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 3 ALERT type 3 Indicator that the structure quality may be low 2 ALERT type 4 Improvement, methodology, query or suggestion 1 ALERT type 5 Informative message, check

Computing details top

Data collection: APEX2 (Bruker, 2013); cell refinement: SAINT (Bruker, 2013); data reduction: SAINT (Bruker, 2013); program(s) used to solve structure: SHELXT (Sheldrick, 2015); program(s) used to refine structure: XL (Sheldrick, 2008); molecular graphics: OLEX2 (Dolomanov et al., 2009); software used to prepare material for publication: OLEX2 (Dolomanov et al., 2009).

Bis{2-[({[3-(dimethylazaniumyl)propyl]imino}methyl)phenyl]sulfanido}nickel(II) tetraphenylborate top
Crystal data top
[Ni(C12H18N2S2)2](C24H20B)2F(000) = 2424
Mr = 1141.81Dx = 1.284 Mg m3
Monoclinic, C2/cMo Kα radiation, λ = 0.71073 Å
a = 16.376 (2) ÅCell parameters from 4652 reflections
b = 9.9864 (14) Åθ = 2.6–24.3°
c = 36.605 (5) ŵ = 0.45 mm1
β = 99.419 (4)°T = 150 K
V = 5905.6 (14) Å3Block, violet
Z = 40.63 × 0.60 × 0.34 mm
Data collection top
Bruker APEXII CCD
diffractometer
6401 independent reflections
Radiation source: sealed X-ray tube4454 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.076
Detector resolution: 5.6 pixels mm-1θmax = 27.1°, θmin = 3.1°
φ and ω scansh = 2020
Absorption correction: numerical
(SADABS; Bruker, 2012)
k = 1212
Tmin = 0.599, Tmax = 0.746l = 4646
30373 measured reflections
Refinement top
Refinement on F2Primary atom site location: dual
Least-squares matrix: fullHydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.054H-atom parameters constrained
wR(F2) = 0.109 w = 1/[σ2(Fo2) + (0.029P)2 + 11.6381P]
where P = (Fo2 + 2Fc2)/3
S = 1.05(Δ/σ)max = 0.001
6401 reflectionsΔρmax = 0.30 e Å3
368 parametersΔρmin = 0.71 e Å3
0 restraints
Special details top

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.

Refinement. 1. Fixed Uiso

At 1.2 times of:

All C(H) groups, All C(H,H) groups, All N(H) groups

At 1.5 times of:

All C(H,H,H) groups

2.a Ternary CH refined with riding coordinates:

N2(H2)

2.b Secondary CH2 refined with riding coordinates:

C8(H8A,H8B), C9(H9A,H9B), C10(H10A,H10B)

2.c Aromatic/amide H refined with riding coordinates:

C18(H18), C3(H3), C17(H17), C15(H15), C1(H1), C16(H16), C14(H14), C6(H6),

C32(H32), C5(H5), C4(H4), C33(H33), C34(H34), C36(H36), C35(H35), C24(H24),

C26(H26), C23(H23), C20(H20), C21(H21), C30(H30), C22(H22), C29(H29), C27(H27),

C28(H28)

2.d Idealised Me refined as rotating group:

C11(H11A,H11B,H11C), C12(H12A,H12B,H12C)

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
Ni10.50000.94419 (5)0.75000.01869 (13)
S10.40969 (4)1.10165 (7)0.75171 (2)0.02515 (18)
N10.41471 (13)0.8114 (2)0.73848 (6)0.0198 (5)
N20.40986 (14)0.9765 (2)0.62926 (6)0.0281 (6)
H20.43570.92250.61200.034*
C180.50475 (16)0.4326 (3)0.66288 (7)0.0220 (6)
H180.45150.40900.65180.026*
C30.26569 (17)0.8453 (3)0.80122 (8)0.0271 (7)
H30.24630.75770.79840.033*
C20.32047 (16)0.8932 (3)0.77834 (7)0.0211 (6)
C170.52741 (18)0.4125 (3)0.70094 (8)0.0275 (7)
H170.48960.37580.71450.033*
C150.66161 (19)0.4988 (3)0.69757 (8)0.0285 (7)
H150.71490.52100.70890.034*
C130.55877 (17)0.4869 (2)0.64052 (7)0.0209 (6)
C10.34617 (17)0.8015 (3)0.75121 (7)0.0218 (6)
H10.31070.73150.74260.026*
C310.45004 (16)0.4282 (3)0.57731 (7)0.0208 (6)
C160.60599 (19)0.4470 (3)0.71857 (8)0.0281 (6)
H160.62110.43560.74400.034*
C140.63840 (17)0.5177 (3)0.65982 (8)0.0253 (6)
H140.67730.55260.64650.030*
C60.31900 (17)1.1093 (3)0.80796 (8)0.0274 (7)
H60.33531.19850.81020.033*
C190.61271 (16)0.4398 (3)0.57707 (7)0.0209 (6)
C320.37278 (16)0.4651 (3)0.58659 (8)0.0247 (6)
H320.37110.53400.60350.030*
C50.26801 (18)1.0579 (3)0.83128 (8)0.0318 (7)
H50.25221.11230.84950.038*
C250.52708 (16)0.6677 (3)0.58324 (8)0.0215 (6)
C80.42913 (17)0.7166 (3)0.70892 (7)0.0226 (6)
H8A0.37940.66430.70110.027*
H8B0.47340.65550.71860.027*
C70.34641 (16)1.0285 (3)0.78095 (7)0.0223 (6)
C40.24024 (17)0.9263 (3)0.82782 (8)0.0303 (7)
H40.20500.89320.84320.036*
C330.29891 (18)0.4027 (3)0.57146 (8)0.0303 (7)
H330.24960.42920.57880.036*
C340.29856 (18)0.3015 (3)0.54565 (8)0.0297 (7)
H340.24940.25910.53560.036*
C360.44618 (18)0.3265 (3)0.55081 (7)0.0241 (6)
H360.49520.29890.54340.029*
C350.37274 (18)0.2643 (3)0.53491 (8)0.0292 (7)
H350.37350.19800.51710.035*
C240.64779 (17)0.3167 (3)0.59048 (8)0.0253 (6)
H240.63040.27860.61110.030*
C260.57679 (17)0.7696 (3)0.60160 (8)0.0261 (6)
H260.61330.74810.62300.031*
C230.70681 (19)0.2500 (3)0.57433 (8)0.0337 (7)
H230.72790.16860.58400.040*
C200.64204 (17)0.4912 (3)0.54601 (7)0.0252 (6)
H200.62090.57210.53610.030*
C90.45220 (17)0.7912 (3)0.67557 (7)0.0253 (6)
H9A0.50180.84360.68350.030*
H9B0.46450.72660.65740.030*
C210.70175 (18)0.4253 (3)0.52945 (8)0.0337 (7)
H210.71940.46240.50880.040*
C300.47271 (19)0.7095 (3)0.55167 (8)0.0328 (7)
H300.43790.64620.53850.039*
C220.7346 (2)0.3050 (3)0.54369 (8)0.0371 (8)
H220.77490.26140.53290.045*
C100.38377 (18)0.8832 (3)0.65759 (8)0.0294 (7)
H10A0.33780.82910.64570.035*
H10B0.36440.93600.67670.035*
C290.4683 (2)0.8411 (3)0.53907 (10)0.0410 (8)
H290.43110.86390.51800.049*
C270.57369 (19)0.9017 (3)0.58911 (9)0.0346 (8)
H270.60860.96540.60190.042*
C280.5191 (2)0.9386 (3)0.55781 (9)0.0386 (8)
H280.51651.02670.54950.046*
C110.4715 (2)1.0792 (3)0.64582 (9)0.0417 (8)
H11A0.45031.12640.66510.063*
H11B0.48131.14130.62700.063*
H11C0.52251.03570.65600.063*
C120.3369 (2)1.0444 (4)0.60779 (10)0.0535 (10)
H12A0.29760.97850.59700.080*
H12B0.35421.09730.58850.080*
H12C0.31191.10140.62390.080*
B10.53614 (19)0.5067 (3)0.59512 (9)0.0214 (7)
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Ni10.0205 (3)0.0140 (2)0.0217 (3)0.0000.0037 (2)0.000
S10.0272 (4)0.0168 (3)0.0323 (4)0.0024 (3)0.0072 (3)0.0020 (3)
N10.0215 (12)0.0168 (11)0.0205 (12)0.0004 (9)0.0020 (10)0.0006 (9)
N20.0271 (14)0.0309 (14)0.0257 (14)0.0052 (11)0.0028 (11)0.0043 (11)
C180.0215 (14)0.0193 (13)0.0264 (15)0.0002 (11)0.0080 (12)0.0000 (12)
C30.0209 (15)0.0306 (15)0.0304 (17)0.0036 (12)0.0057 (13)0.0045 (13)
C20.0198 (14)0.0234 (13)0.0197 (15)0.0043 (11)0.0019 (12)0.0027 (11)
C170.0355 (17)0.0231 (15)0.0268 (16)0.0032 (12)0.0140 (14)0.0013 (12)
C150.0333 (17)0.0238 (14)0.0265 (16)0.0030 (13)0.0005 (13)0.0022 (13)
C130.0249 (15)0.0148 (13)0.0235 (15)0.0011 (11)0.0058 (12)0.0006 (11)
C10.0216 (15)0.0202 (13)0.0227 (15)0.0010 (11)0.0009 (12)0.0008 (12)
C310.0238 (14)0.0189 (13)0.0195 (14)0.0005 (11)0.0033 (11)0.0046 (11)
C160.0443 (18)0.0236 (14)0.0162 (14)0.0084 (14)0.0040 (13)0.0005 (12)
C140.0261 (16)0.0234 (15)0.0269 (16)0.0033 (12)0.0055 (13)0.0032 (12)
C60.0253 (16)0.0261 (15)0.0294 (17)0.0058 (12)0.0007 (13)0.0009 (13)
C190.0200 (14)0.0239 (14)0.0182 (14)0.0049 (12)0.0014 (11)0.0020 (12)
C320.0271 (16)0.0226 (15)0.0243 (15)0.0015 (12)0.0044 (12)0.0014 (12)
C50.0281 (16)0.0417 (18)0.0258 (16)0.0114 (15)0.0051 (13)0.0018 (14)
C250.0188 (14)0.0219 (14)0.0247 (15)0.0015 (11)0.0066 (12)0.0012 (12)
C80.0278 (16)0.0179 (13)0.0210 (15)0.0010 (11)0.0011 (12)0.0029 (11)
C70.0204 (14)0.0223 (14)0.0228 (15)0.0040 (11)0.0001 (12)0.0020 (11)
C40.0257 (16)0.0400 (18)0.0275 (16)0.0073 (13)0.0107 (13)0.0057 (14)
C330.0210 (15)0.0350 (16)0.0346 (18)0.0023 (13)0.0036 (13)0.0070 (14)
C340.0267 (16)0.0303 (16)0.0290 (17)0.0076 (13)0.0047 (13)0.0062 (13)
C360.0264 (15)0.0236 (14)0.0228 (15)0.0014 (12)0.0056 (12)0.0024 (12)
C350.0368 (18)0.0244 (15)0.0246 (16)0.0023 (13)0.0005 (14)0.0016 (12)
C240.0279 (16)0.0264 (15)0.0227 (15)0.0027 (12)0.0072 (13)0.0028 (12)
C260.0264 (16)0.0244 (15)0.0274 (16)0.0002 (12)0.0045 (13)0.0011 (12)
C230.0368 (19)0.0320 (17)0.0325 (18)0.0129 (14)0.0062 (15)0.0018 (14)
C200.0232 (15)0.0291 (15)0.0226 (15)0.0021 (12)0.0018 (12)0.0022 (12)
C90.0274 (16)0.0258 (15)0.0231 (16)0.0010 (12)0.0050 (13)0.0060 (12)
C210.0340 (17)0.0462 (19)0.0227 (16)0.0015 (15)0.0093 (13)0.0014 (14)
C300.0345 (18)0.0277 (16)0.0337 (18)0.0060 (14)0.0011 (14)0.0044 (14)
C220.0356 (18)0.050 (2)0.0288 (18)0.0124 (16)0.0132 (15)0.0058 (15)
C100.0286 (17)0.0350 (16)0.0246 (16)0.0058 (13)0.0045 (13)0.0067 (13)
C290.038 (2)0.0376 (18)0.045 (2)0.0018 (15)0.0015 (16)0.0166 (16)
C270.0342 (18)0.0243 (15)0.047 (2)0.0066 (13)0.0123 (16)0.0037 (14)
C280.0411 (19)0.0229 (15)0.054 (2)0.0015 (15)0.0138 (17)0.0105 (15)
C110.047 (2)0.0361 (18)0.042 (2)0.0135 (16)0.0049 (16)0.0022 (15)
C120.043 (2)0.063 (2)0.051 (2)0.0031 (19)0.0010 (17)0.029 (2)
B10.0221 (17)0.0225 (15)0.0198 (17)0.0004 (13)0.0043 (13)0.0031 (13)
Geometric parameters (Å, º) top
Ni1—S12.1665 (8)C25—C301.402 (4)
Ni1—S1i2.1665 (8)C25—B11.665 (4)
Ni1—N1i1.922 (2)C8—H8A0.9700
Ni1—N11.922 (2)C8—H8B0.9700
S1—C71.765 (3)C8—C91.529 (4)
N1—C11.287 (3)C4—H40.9300
N1—C81.485 (3)C33—H330.9300
N2—H20.9800C33—C341.383 (4)
N2—C101.507 (3)C34—H340.9300
N2—C111.496 (4)C34—C351.387 (4)
N2—C121.482 (4)C36—H360.9300
C18—H180.9300C36—C351.393 (4)
C18—C171.396 (4)C35—H350.9300
C18—C131.409 (4)C24—H240.9300
C3—H30.9300C24—C231.383 (4)
C3—C21.408 (4)C26—H260.9300
C3—C41.381 (4)C26—C271.394 (4)
C2—C11.463 (4)C23—H230.9300
C2—C71.414 (4)C23—C221.391 (4)
C17—H170.9300C20—H200.9300
C17—C161.385 (4)C20—C211.396 (4)
C15—H150.9300C9—H9A0.9700
C15—C161.385 (4)C9—H9B0.9700
C15—C141.385 (4)C9—C101.513 (4)
C13—C141.412 (4)C21—H210.9300
C13—B11.654 (4)C21—C221.384 (4)
C1—H10.9300C30—H300.9300
C31—C321.411 (4)C30—C291.391 (4)
C31—C361.399 (4)C22—H220.9300
C31—B11.651 (4)C10—H10A0.9700
C16—H160.9300C10—H10B0.9700
C14—H140.9300C29—H290.9300
C6—H60.9300C29—C281.386 (4)
C6—C51.387 (4)C27—H270.9300
C6—C71.406 (4)C27—C281.383 (4)
C19—C241.411 (4)C28—H280.9300
C19—C201.402 (4)C11—H11A0.9600
C19—B11.651 (4)C11—H11B0.9600
C32—H320.9300C11—H11C0.9600
C32—C331.392 (4)C12—H12A0.9600
C5—H50.9300C12—H12B0.9600
C5—C41.390 (4)C12—H12C0.9600
C25—C261.404 (4)
S1—Ni1—S1i86.93 (4)C32—C33—H33119.8
N1—Ni1—S1i165.78 (7)C34—C33—C32120.3 (3)
N1i—Ni1—S1165.78 (7)C34—C33—H33119.8
N1—Ni1—S191.85 (7)C33—C34—H34120.6
N1i—Ni1—S1i91.85 (7)C33—C34—C35118.9 (3)
N1i—Ni1—N192.73 (13)C35—C34—H34120.6
C7—S1—Ni1100.86 (9)C31—C36—H36118.3
C1—N1—Ni1128.23 (19)C35—C36—C31123.4 (3)
C1—N1—C8117.8 (2)C35—C36—H36118.3
C8—N1—Ni1113.76 (16)C34—C35—C36119.9 (3)
C10—N2—H2107.8C34—C35—H35120.1
C11—N2—H2107.8C36—C35—H35120.1
C11—N2—C10113.2 (2)C19—C24—H24118.5
C12—N2—H2107.8C23—C24—C19123.0 (3)
C12—N2—C10110.7 (2)C23—C24—H24118.5
C12—N2—C11109.5 (3)C25—C26—H26118.6
C17—C18—H18118.5C27—C26—C25122.8 (3)
C17—C18—C13123.1 (3)C27—C26—H26118.6
C13—C18—H18118.5C24—C23—H23120.0
C2—C3—H3119.5C24—C23—C22119.9 (3)
C4—C3—H3119.5C22—C23—H23120.0
C4—C3—C2121.0 (3)C19—C20—H20118.7
C3—C2—C1118.2 (2)C21—C20—C19122.5 (3)
C3—C2—C7119.9 (2)C21—C20—H20118.7
C7—C2—C1121.8 (2)C8—C9—H9A109.1
C18—C17—H17119.9C8—C9—H9B109.1
C16—C17—C18120.3 (3)H9A—C9—H9B107.9
C16—C17—H17119.9C10—C9—C8112.4 (2)
C16—C15—H15119.8C10—C9—H9A109.1
C16—C15—C14120.5 (3)C10—C9—H9B109.1
C14—C15—H15119.8C20—C21—H21119.9
C18—C13—C14114.2 (2)C22—C21—C20120.2 (3)
C18—C13—B1124.8 (2)C22—C21—H21119.9
C14—C13—B1120.9 (2)C25—C30—H30118.4
N1—C1—C2124.2 (2)C29—C30—C25123.1 (3)
N1—C1—H1117.9C29—C30—H30118.4
C2—C1—H1117.9C23—C22—H22120.4
C32—C31—B1121.5 (2)C21—C22—C23119.2 (3)
C36—C31—C32114.6 (2)C21—C22—H22120.4
C36—C31—B1123.9 (2)N2—C10—C9113.7 (2)
C17—C16—H16120.7N2—C10—H10A108.8
C15—C16—C17118.6 (3)N2—C10—H10B108.8
C15—C16—H16120.7C9—C10—H10A108.8
C15—C14—C13123.3 (3)C9—C10—H10B108.8
C15—C14—H14118.3H10A—C10—H10B107.7
C13—C14—H14118.3C30—C29—H29119.8
C5—C6—H6119.5C28—C29—C30120.3 (3)
C5—C6—C7120.9 (3)C28—C29—H29119.8
C7—C6—H6119.5C26—C27—H27119.7
C24—C19—B1120.4 (2)C28—C27—C26120.5 (3)
C20—C19—C24115.3 (2)C28—C27—H27119.7
C20—C19—B1124.1 (2)C29—C28—H28120.8
C31—C32—H32118.6C27—C28—C29118.5 (3)
C33—C32—C31122.8 (3)C27—C28—H28120.8
C33—C32—H32118.6N2—C11—H11A109.5
C6—C5—H5119.5N2—C11—H11B109.5
C6—C5—C4121.0 (3)N2—C11—H11C109.5
C4—C5—H5119.5H11A—C11—H11B109.5
C26—C25—B1123.7 (2)H11A—C11—H11C109.5
C30—C25—C26114.8 (2)H11B—C11—H11C109.5
C30—C25—B1121.3 (2)N2—C12—H12A109.5
N1—C8—H8A109.4N2—C12—H12B109.5
N1—C8—H8B109.4N2—C12—H12C109.5
N1—C8—C9111.1 (2)H12A—C12—H12B109.5
H8A—C8—H8B108.0H12A—C12—H12C109.5
C9—C8—H8A109.4H12B—C12—H12C109.5
C9—C8—H8B109.4C13—B1—C25112.0 (2)
C2—C7—S1123.6 (2)C31—B1—C13112.1 (2)
C6—C7—S1118.4 (2)C31—B1—C25108.8 (2)
C6—C7—C2118.0 (2)C19—B1—C13107.1 (2)
C3—C4—C5119.1 (3)C19—B1—C31107.8 (2)
C3—C4—H4120.5C19—B1—C25109.1 (2)
C5—C4—H4120.5
Symmetry code: (i) x+1, y, z+3/2.
Hydrogen-bond geometry (Å, º) top
Cg is the centroid of the C25–C30 ring.
D—H···AD—HH···AD···AD—H···A
N2—H2···Cg0.982.543.510 (3)171
 

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