metal-organic compounds
Bis{2-[({[3-(dimethylazaniumyl)propyl]imino}methyl)phenyl]sulfanido}nickel(II) tetraphenylborate
aDepartment of Chemistry, Wichita State University, 1845 Fairmount, Wichita, KS 67260-0051, USA
*Correspondence e-mail: david.eichhorn@wichita.edu
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.
Keywords: crystal structure; nickel complex.
CCDC reference: 1563052
Structure description
We have previously published the reaction of 2,2′-dithiodibenzaldehyde with NiCl2 and N,N-dimethylethylenediamine to produce a nickel complex of a tridentate ligand in which the Ni is coordinated by the three potential donor atoms (imine N, amine N, and thiolate S) of the ligand with the square-planar Ni coordination sphere completed by a Cl ligand. When Ni(BPh4)2 was used as the nickel source, a related species was isolated in which the fourth coordination site is occupied by a thiolate derived from the tridentate ligand. (Zimmerman, et al., 2011) In an analogous reaction using N,N-dimethylpropylenediamine, the title complex was isolated in which the potentially tridentate ligand utilizes only the imine N and thiolate S atoms to bind to Ni (Table 1).
|
Two ligands coordinate to the Ni atom, related to each other by a crystallographic twofold rotation axis (Fig. 1). The coordination around Ni deviates somewhat from ideal square planar, with the chelate rings of the two ligands rotated by 19.40 (9)° with respect to each other. The amine N atoms are protonated, with each proton participating in a hydrogen bond with a phenyl ring of one BPh4− anion (Fig. 2, Table 2).
|
Synthesis and crystallization
The title compound was synthesized and crystallized by layering a solution of 0.10 g (0.90 mmol) of N,N-dimethylpropylenediamine and 0.701 g (1.0 mmol) of [Ni(BPh4)2] in 20 mL of ethyl acetate on top of a solution of 0.123 g (0.45 mmol) of 2,2′-dithiodibenzaldehyde in 10 mL of dichloromethane.
Refinement
Crystal data, data collection and structure .
details are summarized in Table 3Structural data
CCDC reference: 1563052
https://doi.org/10.1107/S2414314617010677/bv4008sup1.cif
contains datablock I. DOI:Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S2414314617010677/bv4008Isup2.hkl
Data collection: APEX2 (Bruker, 2013); cell
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).[Ni(C12H18N2S2)2](C24H20B)2 | F(000) = 2424 |
Mr = 1141.81 | Dx = 1.284 Mg m−3 |
Monoclinic, C2/c | Mo Kα radiation, λ = 0.71073 Å |
a = 16.376 (2) Å | Cell parameters from 4652 reflections |
b = 9.9864 (14) Å | θ = 2.6–24.3° |
c = 36.605 (5) Å | µ = 0.45 mm−1 |
β = 99.419 (4)° | T = 150 K |
V = 5905.6 (14) Å3 | Block, violet |
Z = 4 | 0.63 × 0.60 × 0.34 mm |
Bruker APEXII CCD diffractometer | 6401 independent reflections |
Radiation source: sealed X-ray tube | 4454 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.076 |
Detector resolution: 5.6 pixels mm-1 | θmax = 27.1°, θmin = 3.1° |
φ and ω scans | h = −20→20 |
Absorption correction: numerical (SADABS; Bruker, 2012) | k = −12→12 |
Tmin = 0.599, Tmax = 0.746 | l = −46→46 |
30373 measured reflections |
Refinement on F2 | Primary atom site location: dual |
Least-squares matrix: full | Hydrogen site location: inferred from neighbouring sites |
R[F2 > 2σ(F2)] = 0.054 | H-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 reflections | Δρmax = 0.30 e Å−3 |
368 parameters | Δρmin = −0.71 e Å−3 |
0 restraints |
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) |
x | y | z | Uiso*/Ueq | ||
Ni1 | 0.5000 | 0.94419 (5) | 0.7500 | 0.01869 (13) | |
S1 | 0.40969 (4) | 1.10165 (7) | 0.75171 (2) | 0.02515 (18) | |
N1 | 0.41471 (13) | 0.8114 (2) | 0.73848 (6) | 0.0198 (5) | |
N2 | 0.40986 (14) | 0.9765 (2) | 0.62926 (6) | 0.0281 (6) | |
H2 | 0.4357 | 0.9225 | 0.6120 | 0.034* | |
C18 | 0.50475 (16) | 0.4326 (3) | 0.66288 (7) | 0.0220 (6) | |
H18 | 0.4515 | 0.4090 | 0.6518 | 0.026* | |
C3 | 0.26569 (17) | 0.8453 (3) | 0.80122 (8) | 0.0271 (7) | |
H3 | 0.2463 | 0.7577 | 0.7984 | 0.033* | |
C2 | 0.32047 (16) | 0.8932 (3) | 0.77834 (7) | 0.0211 (6) | |
C17 | 0.52741 (18) | 0.4125 (3) | 0.70094 (8) | 0.0275 (7) | |
H17 | 0.4896 | 0.3758 | 0.7145 | 0.033* | |
C15 | 0.66161 (19) | 0.4988 (3) | 0.69757 (8) | 0.0285 (7) | |
H15 | 0.7149 | 0.5210 | 0.7089 | 0.034* | |
C13 | 0.55877 (17) | 0.4869 (2) | 0.64052 (7) | 0.0209 (6) | |
C1 | 0.34617 (17) | 0.8015 (3) | 0.75121 (7) | 0.0218 (6) | |
H1 | 0.3107 | 0.7315 | 0.7426 | 0.026* | |
C31 | 0.45004 (16) | 0.4282 (3) | 0.57731 (7) | 0.0208 (6) | |
C16 | 0.60599 (19) | 0.4470 (3) | 0.71857 (8) | 0.0281 (6) | |
H16 | 0.6211 | 0.4356 | 0.7440 | 0.034* | |
C14 | 0.63840 (17) | 0.5177 (3) | 0.65982 (8) | 0.0253 (6) | |
H14 | 0.6773 | 0.5526 | 0.6465 | 0.030* | |
C6 | 0.31900 (17) | 1.1093 (3) | 0.80796 (8) | 0.0274 (7) | |
H6 | 0.3353 | 1.1985 | 0.8102 | 0.033* | |
C19 | 0.61271 (16) | 0.4398 (3) | 0.57707 (7) | 0.0209 (6) | |
C32 | 0.37278 (16) | 0.4651 (3) | 0.58659 (8) | 0.0247 (6) | |
H32 | 0.3711 | 0.5340 | 0.6035 | 0.030* | |
C5 | 0.26801 (18) | 1.0579 (3) | 0.83128 (8) | 0.0318 (7) | |
H5 | 0.2522 | 1.1123 | 0.8495 | 0.038* | |
C25 | 0.52708 (16) | 0.6677 (3) | 0.58324 (8) | 0.0215 (6) | |
C8 | 0.42913 (17) | 0.7166 (3) | 0.70892 (7) | 0.0226 (6) | |
H8A | 0.3794 | 0.6643 | 0.7011 | 0.027* | |
H8B | 0.4734 | 0.6555 | 0.7186 | 0.027* | |
C7 | 0.34641 (16) | 1.0285 (3) | 0.78095 (7) | 0.0223 (6) | |
C4 | 0.24024 (17) | 0.9263 (3) | 0.82782 (8) | 0.0303 (7) | |
H4 | 0.2050 | 0.8932 | 0.8432 | 0.036* | |
C33 | 0.29891 (18) | 0.4027 (3) | 0.57146 (8) | 0.0303 (7) | |
H33 | 0.2496 | 0.4292 | 0.5788 | 0.036* | |
C34 | 0.29856 (18) | 0.3015 (3) | 0.54565 (8) | 0.0297 (7) | |
H34 | 0.2494 | 0.2591 | 0.5356 | 0.036* | |
C36 | 0.44618 (18) | 0.3265 (3) | 0.55081 (7) | 0.0241 (6) | |
H36 | 0.4952 | 0.2989 | 0.5434 | 0.029* | |
C35 | 0.37274 (18) | 0.2643 (3) | 0.53491 (8) | 0.0292 (7) | |
H35 | 0.3735 | 0.1980 | 0.5171 | 0.035* | |
C24 | 0.64779 (17) | 0.3167 (3) | 0.59048 (8) | 0.0253 (6) | |
H24 | 0.6304 | 0.2786 | 0.6111 | 0.030* | |
C26 | 0.57679 (17) | 0.7696 (3) | 0.60160 (8) | 0.0261 (6) | |
H26 | 0.6133 | 0.7481 | 0.6230 | 0.031* | |
C23 | 0.70681 (19) | 0.2500 (3) | 0.57433 (8) | 0.0337 (7) | |
H23 | 0.7279 | 0.1686 | 0.5840 | 0.040* | |
C20 | 0.64204 (17) | 0.4912 (3) | 0.54601 (7) | 0.0252 (6) | |
H20 | 0.6209 | 0.5721 | 0.5361 | 0.030* | |
C9 | 0.45220 (17) | 0.7912 (3) | 0.67557 (7) | 0.0253 (6) | |
H9A | 0.5018 | 0.8436 | 0.6835 | 0.030* | |
H9B | 0.4645 | 0.7266 | 0.6574 | 0.030* | |
C21 | 0.70175 (18) | 0.4253 (3) | 0.52945 (8) | 0.0337 (7) | |
H21 | 0.7194 | 0.4624 | 0.5088 | 0.040* | |
C30 | 0.47271 (19) | 0.7095 (3) | 0.55167 (8) | 0.0328 (7) | |
H30 | 0.4379 | 0.6462 | 0.5385 | 0.039* | |
C22 | 0.7346 (2) | 0.3050 (3) | 0.54369 (8) | 0.0371 (8) | |
H22 | 0.7749 | 0.2614 | 0.5329 | 0.045* | |
C10 | 0.38377 (18) | 0.8832 (3) | 0.65759 (8) | 0.0294 (7) | |
H10A | 0.3378 | 0.8291 | 0.6457 | 0.035* | |
H10B | 0.3644 | 0.9360 | 0.6767 | 0.035* | |
C29 | 0.4683 (2) | 0.8411 (3) | 0.53907 (10) | 0.0410 (8) | |
H29 | 0.4311 | 0.8639 | 0.5180 | 0.049* | |
C27 | 0.57369 (19) | 0.9017 (3) | 0.58911 (9) | 0.0346 (8) | |
H27 | 0.6086 | 0.9654 | 0.6019 | 0.042* | |
C28 | 0.5191 (2) | 0.9386 (3) | 0.55781 (9) | 0.0386 (8) | |
H28 | 0.5165 | 1.0267 | 0.5495 | 0.046* | |
C11 | 0.4715 (2) | 1.0792 (3) | 0.64582 (9) | 0.0417 (8) | |
H11A | 0.4503 | 1.1264 | 0.6651 | 0.063* | |
H11B | 0.4813 | 1.1413 | 0.6270 | 0.063* | |
H11C | 0.5225 | 1.0357 | 0.6560 | 0.063* | |
C12 | 0.3369 (2) | 1.0444 (4) | 0.60779 (10) | 0.0535 (10) | |
H12A | 0.2976 | 0.9785 | 0.5970 | 0.080* | |
H12B | 0.3542 | 1.0973 | 0.5885 | 0.080* | |
H12C | 0.3119 | 1.1014 | 0.6239 | 0.080* | |
B1 | 0.53614 (19) | 0.5067 (3) | 0.59512 (9) | 0.0214 (7) |
U11 | U22 | U33 | U12 | U13 | U23 | |
Ni1 | 0.0205 (3) | 0.0140 (2) | 0.0217 (3) | 0.000 | 0.0037 (2) | 0.000 |
S1 | 0.0272 (4) | 0.0168 (3) | 0.0323 (4) | 0.0024 (3) | 0.0072 (3) | 0.0020 (3) |
N1 | 0.0215 (12) | 0.0168 (11) | 0.0205 (12) | 0.0004 (9) | 0.0020 (10) | 0.0006 (9) |
N2 | 0.0271 (14) | 0.0309 (14) | 0.0257 (14) | −0.0052 (11) | 0.0028 (11) | 0.0043 (11) |
C18 | 0.0215 (14) | 0.0193 (13) | 0.0264 (15) | −0.0002 (11) | 0.0080 (12) | 0.0000 (12) |
C3 | 0.0209 (15) | 0.0306 (15) | 0.0304 (17) | 0.0036 (12) | 0.0057 (13) | 0.0045 (13) |
C2 | 0.0198 (14) | 0.0234 (13) | 0.0197 (15) | 0.0043 (11) | 0.0019 (12) | 0.0027 (11) |
C17 | 0.0355 (17) | 0.0231 (15) | 0.0268 (16) | 0.0032 (12) | 0.0140 (14) | 0.0013 (12) |
C15 | 0.0333 (17) | 0.0238 (14) | 0.0265 (16) | −0.0030 (13) | −0.0005 (13) | −0.0022 (13) |
C13 | 0.0249 (15) | 0.0148 (13) | 0.0235 (15) | 0.0011 (11) | 0.0058 (12) | −0.0006 (11) |
C1 | 0.0216 (15) | 0.0202 (13) | 0.0227 (15) | −0.0010 (11) | 0.0009 (12) | 0.0008 (12) |
C31 | 0.0238 (14) | 0.0189 (13) | 0.0195 (14) | 0.0005 (11) | 0.0033 (11) | 0.0046 (11) |
C16 | 0.0443 (18) | 0.0236 (14) | 0.0162 (14) | 0.0084 (14) | 0.0040 (13) | 0.0005 (12) |
C14 | 0.0261 (16) | 0.0234 (15) | 0.0269 (16) | −0.0033 (12) | 0.0055 (13) | 0.0032 (12) |
C6 | 0.0253 (16) | 0.0261 (15) | 0.0294 (17) | 0.0058 (12) | 0.0007 (13) | −0.0009 (13) |
C19 | 0.0200 (14) | 0.0239 (14) | 0.0182 (14) | −0.0049 (12) | 0.0014 (11) | −0.0020 (12) |
C32 | 0.0271 (16) | 0.0226 (15) | 0.0243 (15) | 0.0015 (12) | 0.0044 (12) | −0.0014 (12) |
C5 | 0.0281 (16) | 0.0417 (18) | 0.0258 (16) | 0.0114 (15) | 0.0051 (13) | −0.0018 (14) |
C25 | 0.0188 (14) | 0.0219 (14) | 0.0247 (15) | 0.0015 (11) | 0.0066 (12) | 0.0012 (12) |
C8 | 0.0278 (16) | 0.0179 (13) | 0.0210 (15) | −0.0010 (11) | 0.0011 (12) | −0.0029 (11) |
C7 | 0.0204 (14) | 0.0223 (14) | 0.0228 (15) | 0.0040 (11) | −0.0001 (12) | 0.0020 (11) |
C4 | 0.0257 (16) | 0.0400 (18) | 0.0275 (16) | 0.0073 (13) | 0.0107 (13) | 0.0057 (14) |
C33 | 0.0210 (15) | 0.0350 (16) | 0.0346 (18) | 0.0023 (13) | 0.0036 (13) | 0.0070 (14) |
C34 | 0.0267 (16) | 0.0303 (16) | 0.0290 (17) | −0.0076 (13) | −0.0047 (13) | 0.0062 (13) |
C36 | 0.0264 (15) | 0.0236 (14) | 0.0228 (15) | 0.0014 (12) | 0.0056 (12) | 0.0024 (12) |
C35 | 0.0368 (18) | 0.0244 (15) | 0.0246 (16) | −0.0023 (13) | −0.0005 (14) | −0.0016 (12) |
C24 | 0.0279 (16) | 0.0264 (15) | 0.0227 (15) | 0.0027 (12) | 0.0072 (13) | 0.0028 (12) |
C26 | 0.0264 (16) | 0.0244 (15) | 0.0274 (16) | −0.0002 (12) | 0.0045 (13) | −0.0011 (12) |
C23 | 0.0368 (19) | 0.0320 (17) | 0.0325 (18) | 0.0129 (14) | 0.0062 (15) | 0.0018 (14) |
C20 | 0.0232 (15) | 0.0291 (15) | 0.0226 (15) | 0.0021 (12) | 0.0018 (12) | 0.0022 (12) |
C9 | 0.0274 (16) | 0.0258 (15) | 0.0231 (16) | −0.0010 (12) | 0.0050 (13) | −0.0060 (12) |
C21 | 0.0340 (17) | 0.0462 (19) | 0.0227 (16) | −0.0015 (15) | 0.0093 (13) | 0.0014 (14) |
C30 | 0.0345 (18) | 0.0277 (16) | 0.0337 (18) | −0.0060 (14) | −0.0011 (14) | 0.0044 (14) |
C22 | 0.0356 (18) | 0.050 (2) | 0.0288 (18) | 0.0124 (16) | 0.0132 (15) | −0.0058 (15) |
C10 | 0.0286 (17) | 0.0350 (16) | 0.0246 (16) | −0.0058 (13) | 0.0045 (13) | 0.0067 (13) |
C29 | 0.038 (2) | 0.0376 (18) | 0.045 (2) | 0.0018 (15) | −0.0015 (16) | 0.0166 (16) |
C27 | 0.0342 (18) | 0.0243 (15) | 0.047 (2) | −0.0066 (13) | 0.0123 (16) | −0.0037 (14) |
C28 | 0.0411 (19) | 0.0229 (15) | 0.054 (2) | 0.0015 (15) | 0.0138 (17) | 0.0105 (15) |
C11 | 0.047 (2) | 0.0361 (18) | 0.042 (2) | −0.0135 (16) | 0.0049 (16) | 0.0022 (15) |
C12 | 0.043 (2) | 0.063 (2) | 0.051 (2) | −0.0031 (19) | −0.0010 (17) | 0.029 (2) |
B1 | 0.0221 (17) | 0.0225 (15) | 0.0198 (17) | −0.0004 (13) | 0.0043 (13) | 0.0031 (13) |
Ni1—S1 | 2.1665 (8) | C25—C30 | 1.402 (4) |
Ni1—S1i | 2.1665 (8) | C25—B1 | 1.665 (4) |
Ni1—N1i | 1.922 (2) | C8—H8A | 0.9700 |
Ni1—N1 | 1.922 (2) | C8—H8B | 0.9700 |
S1—C7 | 1.765 (3) | C8—C9 | 1.529 (4) |
N1—C1 | 1.287 (3) | C4—H4 | 0.9300 |
N1—C8 | 1.485 (3) | C33—H33 | 0.9300 |
N2—H2 | 0.9800 | C33—C34 | 1.383 (4) |
N2—C10 | 1.507 (3) | C34—H34 | 0.9300 |
N2—C11 | 1.496 (4) | C34—C35 | 1.387 (4) |
N2—C12 | 1.482 (4) | C36—H36 | 0.9300 |
C18—H18 | 0.9300 | C36—C35 | 1.393 (4) |
C18—C17 | 1.396 (4) | C35—H35 | 0.9300 |
C18—C13 | 1.409 (4) | C24—H24 | 0.9300 |
C3—H3 | 0.9300 | C24—C23 | 1.383 (4) |
C3—C2 | 1.408 (4) | C26—H26 | 0.9300 |
C3—C4 | 1.381 (4) | C26—C27 | 1.394 (4) |
C2—C1 | 1.463 (4) | C23—H23 | 0.9300 |
C2—C7 | 1.414 (4) | C23—C22 | 1.391 (4) |
C17—H17 | 0.9300 | C20—H20 | 0.9300 |
C17—C16 | 1.385 (4) | C20—C21 | 1.396 (4) |
C15—H15 | 0.9300 | C9—H9A | 0.9700 |
C15—C16 | 1.385 (4) | C9—H9B | 0.9700 |
C15—C14 | 1.385 (4) | C9—C10 | 1.513 (4) |
C13—C14 | 1.412 (4) | C21—H21 | 0.9300 |
C13—B1 | 1.654 (4) | C21—C22 | 1.384 (4) |
C1—H1 | 0.9300 | C30—H30 | 0.9300 |
C31—C32 | 1.411 (4) | C30—C29 | 1.391 (4) |
C31—C36 | 1.399 (4) | C22—H22 | 0.9300 |
C31—B1 | 1.651 (4) | C10—H10A | 0.9700 |
C16—H16 | 0.9300 | C10—H10B | 0.9700 |
C14—H14 | 0.9300 | C29—H29 | 0.9300 |
C6—H6 | 0.9300 | C29—C28 | 1.386 (4) |
C6—C5 | 1.387 (4) | C27—H27 | 0.9300 |
C6—C7 | 1.406 (4) | C27—C28 | 1.383 (4) |
C19—C24 | 1.411 (4) | C28—H28 | 0.9300 |
C19—C20 | 1.402 (4) | C11—H11A | 0.9600 |
C19—B1 | 1.651 (4) | C11—H11B | 0.9600 |
C32—H32 | 0.9300 | C11—H11C | 0.9600 |
C32—C33 | 1.392 (4) | C12—H12A | 0.9600 |
C5—H5 | 0.9300 | C12—H12B | 0.9600 |
C5—C4 | 1.390 (4) | C12—H12C | 0.9600 |
C25—C26 | 1.404 (4) | ||
S1—Ni1—S1i | 86.93 (4) | C32—C33—H33 | 119.8 |
N1—Ni1—S1i | 165.78 (7) | C34—C33—C32 | 120.3 (3) |
N1i—Ni1—S1 | 165.78 (7) | C34—C33—H33 | 119.8 |
N1—Ni1—S1 | 91.85 (7) | C33—C34—H34 | 120.6 |
N1i—Ni1—S1i | 91.85 (7) | C33—C34—C35 | 118.9 (3) |
N1i—Ni1—N1 | 92.73 (13) | C35—C34—H34 | 120.6 |
C7—S1—Ni1 | 100.86 (9) | C31—C36—H36 | 118.3 |
C1—N1—Ni1 | 128.23 (19) | C35—C36—C31 | 123.4 (3) |
C1—N1—C8 | 117.8 (2) | C35—C36—H36 | 118.3 |
C8—N1—Ni1 | 113.76 (16) | C34—C35—C36 | 119.9 (3) |
C10—N2—H2 | 107.8 | C34—C35—H35 | 120.1 |
C11—N2—H2 | 107.8 | C36—C35—H35 | 120.1 |
C11—N2—C10 | 113.2 (2) | C19—C24—H24 | 118.5 |
C12—N2—H2 | 107.8 | C23—C24—C19 | 123.0 (3) |
C12—N2—C10 | 110.7 (2) | C23—C24—H24 | 118.5 |
C12—N2—C11 | 109.5 (3) | C25—C26—H26 | 118.6 |
C17—C18—H18 | 118.5 | C27—C26—C25 | 122.8 (3) |
C17—C18—C13 | 123.1 (3) | C27—C26—H26 | 118.6 |
C13—C18—H18 | 118.5 | C24—C23—H23 | 120.0 |
C2—C3—H3 | 119.5 | C24—C23—C22 | 119.9 (3) |
C4—C3—H3 | 119.5 | C22—C23—H23 | 120.0 |
C4—C3—C2 | 121.0 (3) | C19—C20—H20 | 118.7 |
C3—C2—C1 | 118.2 (2) | C21—C20—C19 | 122.5 (3) |
C3—C2—C7 | 119.9 (2) | C21—C20—H20 | 118.7 |
C7—C2—C1 | 121.8 (2) | C8—C9—H9A | 109.1 |
C18—C17—H17 | 119.9 | C8—C9—H9B | 109.1 |
C16—C17—C18 | 120.3 (3) | H9A—C9—H9B | 107.9 |
C16—C17—H17 | 119.9 | C10—C9—C8 | 112.4 (2) |
C16—C15—H15 | 119.8 | C10—C9—H9A | 109.1 |
C16—C15—C14 | 120.5 (3) | C10—C9—H9B | 109.1 |
C14—C15—H15 | 119.8 | C20—C21—H21 | 119.9 |
C18—C13—C14 | 114.2 (2) | C22—C21—C20 | 120.2 (3) |
C18—C13—B1 | 124.8 (2) | C22—C21—H21 | 119.9 |
C14—C13—B1 | 120.9 (2) | C25—C30—H30 | 118.4 |
N1—C1—C2 | 124.2 (2) | C29—C30—C25 | 123.1 (3) |
N1—C1—H1 | 117.9 | C29—C30—H30 | 118.4 |
C2—C1—H1 | 117.9 | C23—C22—H22 | 120.4 |
C32—C31—B1 | 121.5 (2) | C21—C22—C23 | 119.2 (3) |
C36—C31—C32 | 114.6 (2) | C21—C22—H22 | 120.4 |
C36—C31—B1 | 123.9 (2) | N2—C10—C9 | 113.7 (2) |
C17—C16—H16 | 120.7 | N2—C10—H10A | 108.8 |
C15—C16—C17 | 118.6 (3) | N2—C10—H10B | 108.8 |
C15—C16—H16 | 120.7 | C9—C10—H10A | 108.8 |
C15—C14—C13 | 123.3 (3) | C9—C10—H10B | 108.8 |
C15—C14—H14 | 118.3 | H10A—C10—H10B | 107.7 |
C13—C14—H14 | 118.3 | C30—C29—H29 | 119.8 |
C5—C6—H6 | 119.5 | C28—C29—C30 | 120.3 (3) |
C5—C6—C7 | 120.9 (3) | C28—C29—H29 | 119.8 |
C7—C6—H6 | 119.5 | C26—C27—H27 | 119.7 |
C24—C19—B1 | 120.4 (2) | C28—C27—C26 | 120.5 (3) |
C20—C19—C24 | 115.3 (2) | C28—C27—H27 | 119.7 |
C20—C19—B1 | 124.1 (2) | C29—C28—H28 | 120.8 |
C31—C32—H32 | 118.6 | C27—C28—C29 | 118.5 (3) |
C33—C32—C31 | 122.8 (3) | C27—C28—H28 | 120.8 |
C33—C32—H32 | 118.6 | N2—C11—H11A | 109.5 |
C6—C5—H5 | 119.5 | N2—C11—H11B | 109.5 |
C6—C5—C4 | 121.0 (3) | N2—C11—H11C | 109.5 |
C4—C5—H5 | 119.5 | H11A—C11—H11B | 109.5 |
C26—C25—B1 | 123.7 (2) | H11A—C11—H11C | 109.5 |
C30—C25—C26 | 114.8 (2) | H11B—C11—H11C | 109.5 |
C30—C25—B1 | 121.3 (2) | N2—C12—H12A | 109.5 |
N1—C8—H8A | 109.4 | N2—C12—H12B | 109.5 |
N1—C8—H8B | 109.4 | N2—C12—H12C | 109.5 |
N1—C8—C9 | 111.1 (2) | H12A—C12—H12B | 109.5 |
H8A—C8—H8B | 108.0 | H12A—C12—H12C | 109.5 |
C9—C8—H8A | 109.4 | H12B—C12—H12C | 109.5 |
C9—C8—H8B | 109.4 | C13—B1—C25 | 112.0 (2) |
C2—C7—S1 | 123.6 (2) | C31—B1—C13 | 112.1 (2) |
C6—C7—S1 | 118.4 (2) | C31—B1—C25 | 108.8 (2) |
C6—C7—C2 | 118.0 (2) | C19—B1—C13 | 107.1 (2) |
C3—C4—C5 | 119.1 (3) | C19—B1—C31 | 107.8 (2) |
C3—C4—H4 | 120.5 | C19—B1—C25 | 109.1 (2) |
C5—C4—H4 | 120.5 |
Symmetry code: (i) −x+1, y, −z+3/2. |
Cg is the centroid of the C25–C30 ring. |
D—H···A | D—H | H···A | D···A | D—H···A |
N2—H2···Cg | 0.98 | 2.54 | 3.510 (3) | 171 |
Acknowledgements
JRZ acknowledges support from the Graduate Assistance in Areas of National Need program of the US Department of Education. DME acknowledges support from the National Center for Research Resources – NIH COBRE Award P20 RR017708.
Funding information
Funding for this research was provided by: Kansas IDeA Network of Biomedical Research Excellence.
References
Bruker (2012). SADABS. Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
Bruker (2013). APEX and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
Dolomanov, O. V., Bourhis, L. J., Gildea, R. J., Howard, J. A. K. & Puschmann, H. (2009). J. Appl. Cryst. 42, 339–341. Web of Science CrossRef CAS IUCr Journals Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar
Sheldrick, G. M. (2015). Acta Cryst. A71, 3–8. Web of Science CrossRef IUCr Journals Google Scholar
Zimmerman, J. R., Smucker, B. W., Dain, R. P., Van Stipdonk, M. J. & Eichhorn, D. M. (2011). Inorg. Chim. Acta, 373, 54–61. CSD CrossRef CAS Google Scholar
This is an open-access article distributed under the terms of the Creative Commons Attribution (CC-BY) Licence, which permits unrestricted use, distribution, and reproduction in any medium, provided the original authors and source are cited.