Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536802011352/ww6025sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S1600536802011352/ww6025Isup2.hkl |
CCDC reference: 193698
Data collection: SMART (Bruker, 2000); cell refinement: SMART; data reduction: SAINT (Bruker, 2000); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: PLATON (Spek, 2002); software used to prepare material for publication: SHELXL97.
[Ni(C8H9N3)2(C8H8N3)](C2N3)·H2O | F(000) = 1216 |
Mr = 583.29 | Dx = 1.482 Mg m−3 |
Monoclinic, P21/n | Mo Kα radiation, λ = 0.71073 Å |
a = 12.168 (2) Å | Cell parameters from 6371 reflections |
b = 11.983 (2) Å | θ = 2.3–25.0° |
c = 18.901 (4) Å | µ = 0.79 mm−1 |
β = 108.43 (3)° | T = 293 K |
V = 2614.6 (9) Å3 | Platelet, purple |
Z = 4 | 0.30 × 0.20 × 0.10 mm |
CCD area detector diffractometer | 10241 independent reflections |
Radiation source: fine-focus sealed tube | 5110 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.046 |
Detector resolution: 15X15microns pixels mm-1 | θmax = 33.5°, θmin = 2.3° |
φ and ω scans | h = −18→18 |
Absorption correction: empirical (using intensity measurements) (SADABS; Bruker, 2000) | k = −17→18 |
Tmin = 0.827, Tmax = 0.924 | l = −16→29 |
24352 measured reflections |
Refinement on F2 | Primary atom site location: structure-invariant direct methods |
Least-squares matrix: full | Secondary atom site location: difference Fourier map |
R[F2 > 2σ(F2)] = 0.051 | Hydrogen site location: difference Fourier map |
wR(F2) = 0.091 | H atoms treated by a mixture of independent and constrained refinement |
S = 0.82 | w = 1/[σ2(Fo2) + (0.0686P)2] where P = (Fo2 + 2Fc2)/3 |
9577 reflections | (Δ/σ)max = 0.001 |
465 parameters | Δρmax = 1.05 e Å−3 |
1 restraint | Δρmin = −0.46 e Å−3 |
Experimental. The complex was characterized by IR spectral analysis. There is a peak of middle intensity at 3563 cm-1 attributable to the H—O stretching vibration, showing that O—H bond exists in the complex. Three strong peaks at 2239, 2203 and 2141 cm-1 are observed which can be assigned to the stretching vibration of the CN triple bond of dicyanamide. The microelemental analysis results (C 53.40, H 4.77, N 28.69%), agree with the formula [Ni(ambi)3][N(CN)2]OH very well (calculated results: C 53.54, H 4.84, N 28.82%). Consequently, another possibility, i.e. [Ni(ambi)3][N(CN)2]Cl (calculated values: C 51.90, H 4.52, N 27.90%), was dismissed. |
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. |
x | y | z | Uiso*/Ueq | ||
Ni1 | −0.06599 (2) | −0.00528 (2) | 0.227217 (14) | 0.02789 (7) | |
N5 | 0.03389 (13) | 0.12667 (13) | 0.28363 (9) | 0.0296 (4) | |
N2 | 0.00214 (13) | −0.14067 (13) | 0.29673 (9) | 0.0295 (4) | |
N8 | −0.39250 (14) | −0.01274 (14) | 0.25135 (9) | 0.0322 (4) | |
N7 | −0.20695 (13) | 0.02549 (12) | 0.26552 (9) | 0.0287 (4) | |
N1 | 0.05946 (18) | −0.06565 (15) | 0.17822 (12) | 0.0348 (4) | |
N6 | 0.05092 (14) | 0.31548 (13) | 0.29222 (10) | 0.0349 (4) | |
C10 | 0.06425 (16) | −0.20811 (15) | 0.26942 (11) | 0.0299 (4) | |
N9 | −0.19332 (16) | −0.11511 (17) | 0.15608 (13) | 0.0365 (4) | |
C19 | −0.35001 (16) | 0.04503 (15) | 0.31781 (11) | 0.0296 (4) | |
C11 | −0.01400 (16) | −0.19857 (15) | 0.35669 (11) | 0.0290 (4) | |
C12 | 0.04174 (16) | −0.30158 (15) | 0.36360 (11) | 0.0306 (4) | |
C4 | 0.12807 (16) | 0.15245 (16) | 0.34575 (11) | 0.0295 (4) | |
C21 | −0.16495 (19) | 0.12368 (17) | 0.38989 (12) | 0.0352 (5) | |
N4 | −0.1208 (2) | 0.12583 (15) | 0.14706 (11) | 0.0371 (4) | |
N3 | 0.09120 (15) | −0.30449 (14) | 0.30698 (10) | 0.0357 (4) | |
C3 | 0.13833 (16) | 0.26947 (16) | 0.35075 (11) | 0.0304 (4) | |
C20 | −0.23379 (15) | 0.06971 (15) | 0.32596 (11) | 0.0274 (4) | |
C18 | −0.30336 (16) | −0.02266 (15) | 0.22406 (11) | 0.0293 (4) | |
C17 | −0.31011 (19) | −0.0819 (2) | 0.15366 (13) | 0.0379 (5) | |
C9 | 0.0961 (2) | −0.18017 (18) | 0.20167 (14) | 0.0383 (5) | |
C1 | −0.1085 (2) | 0.23264 (18) | 0.18636 (13) | 0.0395 (5) | |
C16 | −0.07469 (18) | −0.16980 (18) | 0.40520 (12) | 0.0359 (5) | |
C2 | −0.00570 (17) | 0.22581 (16) | 0.25545 (11) | 0.0313 (4) | |
C13 | 0.04064 (19) | −0.37790 (18) | 0.41825 (13) | 0.0399 (5) | |
C24 | −0.4001 (2) | 0.07249 (18) | 0.37211 (13) | 0.0380 (5) | |
C8 | 0.22874 (19) | 0.3194 (2) | 0.40620 (13) | 0.0400 (5) | |
C5 | 0.20726 (19) | 0.0842 (2) | 0.39669 (13) | 0.0434 (6) | |
C14 | −0.0210 (2) | −0.3477 (2) | 0.46497 (14) | 0.0435 (6) | |
C23 | −0.3304 (2) | 0.12554 (18) | 0.43452 (13) | 0.0435 (6) | |
C15 | −0.07784 (19) | −0.24574 (19) | 0.45860 (13) | 0.0399 (5) | |
C6 | 0.2970 (2) | 0.1354 (2) | 0.45016 (14) | 0.0521 (7) | |
C7 | 0.3075 (2) | 0.2507 (2) | 0.45476 (14) | 0.0474 (6) | |
C22 | −0.2148 (2) | 0.15088 (18) | 0.44298 (13) | 0.0403 (5) | |
C25 | 0.1217 (2) | 0.1134 (2) | 0.03506 (15) | 0.0465 (6) | |
N10 | 0.0985 (2) | 0.15786 (19) | 0.09151 (12) | 0.0633 (6) | |
C26 | 0.1245 (2) | 0.2593 (2) | 0.11155 (14) | 0.0534 (6) | |
N11 | 0.1410 (2) | 0.3485 (2) | 0.13364 (16) | 0.0925 (9) | |
N12 | 0.1367 (2) | 0.0656 (2) | −0.01348 (13) | 0.0701 (7) | |
O1 | 0.18666 (16) | −0.48457 (16) | 0.24673 (10) | 0.0765 (6) | |
H5 | 0.1977 (17) | 0.0073 (17) | 0.3945 (11) | 0.034 (5)* | |
H21 | −0.0886 (16) | 0.1395 (15) | 0.3955 (10) | 0.029 (5)* | |
H15 | −0.1163 (16) | −0.2259 (16) | 0.4918 (11) | 0.037 (6)* | |
H24 | −0.4737 (16) | 0.0534 (15) | 0.3662 (10) | 0.022 (5)* | |
H1A | 0.1208 (19) | −0.0253 (18) | 0.1897 (12) | 0.040 (6)* | |
H1D | −0.1760 (18) | 0.2444 (17) | 0.1994 (11) | 0.040 (6)* | |
H16 | −0.1080 (15) | −0.1036 (16) | 0.4032 (10) | 0.026 (5)* | |
H4A | −0.186 (2) | 0.1188 (17) | 0.1172 (12) | 0.037 (7)* | |
H17D | −0.3635 (17) | −0.1465 (18) | 0.1448 (11) | 0.044 (6)* | |
H3A | 0.1301 (16) | −0.3575 (13) | 0.2959 (11) | 0.043 (6)* | |
H1C | −0.0993 (16) | 0.2904 (17) | 0.1561 (11) | 0.036 (6)* | |
H8 | 0.2362 (16) | 0.3995 (18) | 0.4091 (11) | 0.039 (6)* | |
H9A | 0.177 (2) | −0.1921 (19) | 0.2116 (12) | 0.055 (7)* | |
H22 | −0.1740 (16) | 0.1845 (16) | 0.4835 (11) | 0.035 (6)* | |
H14 | −0.0263 (18) | −0.3955 (19) | 0.4982 (12) | 0.048 (7)* | |
H7 | 0.3676 (19) | 0.2784 (18) | 0.4895 (12) | 0.046 (7)* | |
H17C | −0.3469 (18) | −0.0301 (17) | 0.1120 (12) | 0.042 (6)* | |
H23 | −0.3608 (16) | 0.1447 (16) | 0.4719 (11) | 0.033 (6)* | |
H8A | −0.454 (2) | −0.0563 (19) | 0.2350 (13) | 0.056 (7)* | |
H9D | −0.1885 (19) | −0.1164 (18) | 0.1157 (13) | 0.042 (7)* | |
H9B | 0.0551 (19) | −0.2300 (19) | 0.1623 (13) | 0.055 (7)* | |
H4B | −0.0700 (18) | 0.1239 (17) | 0.1233 (12) | 0.038 (6)* | |
H9C | −0.177 (2) | −0.183 (2) | 0.1743 (14) | 0.061 (8)* | |
H13 | 0.0837 (18) | −0.4448 (19) | 0.4239 (12) | 0.046 (6)* | |
H1B | 0.0264 (18) | −0.0624 (17) | 0.1293 (13) | 0.038 (6)* | |
H6 | 0.348 (2) | 0.093 (2) | 0.4815 (14) | 0.071 (9)* | |
H101 | 0.1811 | −0.5273 | 0.2813 | 0.085* | |
H100 | 0.1791 | −0.5023 | 0.2019 | 0.085* |
U11 | U22 | U33 | U12 | U13 | U23 | |
Ni1 | 0.03013 (13) | 0.02637 (12) | 0.02827 (13) | −0.00190 (11) | 0.01077 (10) | −0.00005 (12) |
N5 | 0.0283 (8) | 0.0262 (8) | 0.0331 (9) | −0.0001 (7) | 0.0081 (7) | 0.0012 (7) |
N2 | 0.0328 (9) | 0.0286 (8) | 0.0303 (9) | 0.0004 (7) | 0.0145 (7) | 0.0018 (7) |
N8 | 0.0273 (9) | 0.0322 (9) | 0.0369 (10) | −0.0078 (8) | 0.0101 (7) | −0.0057 (8) |
N7 | 0.0276 (8) | 0.0290 (8) | 0.0291 (9) | −0.0028 (6) | 0.0084 (7) | −0.0024 (7) |
N1 | 0.0389 (11) | 0.0347 (10) | 0.0349 (12) | −0.0046 (8) | 0.0177 (9) | 0.0019 (8) |
N6 | 0.0381 (10) | 0.0275 (8) | 0.0394 (11) | −0.0004 (7) | 0.0128 (8) | 0.0006 (8) |
C10 | 0.0306 (10) | 0.0274 (9) | 0.0338 (11) | −0.0035 (8) | 0.0129 (8) | −0.0006 (9) |
N9 | 0.0396 (11) | 0.0369 (11) | 0.0361 (12) | −0.0039 (8) | 0.0164 (9) | −0.0071 (9) |
C19 | 0.0299 (10) | 0.0242 (9) | 0.0339 (12) | 0.0013 (8) | 0.0089 (9) | 0.0001 (8) |
C11 | 0.0300 (10) | 0.0282 (10) | 0.0282 (11) | −0.0023 (8) | 0.0083 (8) | 0.0017 (8) |
C12 | 0.0327 (10) | 0.0261 (9) | 0.0327 (12) | −0.0018 (8) | 0.0098 (9) | 0.0005 (8) |
C4 | 0.0280 (10) | 0.0319 (10) | 0.0300 (11) | 0.0001 (8) | 0.0109 (8) | −0.0019 (8) |
C21 | 0.0330 (12) | 0.0322 (11) | 0.0374 (13) | −0.0021 (9) | 0.0070 (10) | −0.0039 (9) |
N4 | 0.0388 (11) | 0.0377 (10) | 0.0313 (11) | −0.0043 (9) | 0.0058 (10) | 0.0016 (8) |
N3 | 0.0420 (10) | 0.0243 (8) | 0.0469 (12) | 0.0042 (8) | 0.0228 (9) | 0.0015 (8) |
C3 | 0.0312 (10) | 0.0326 (10) | 0.0315 (11) | −0.0034 (8) | 0.0158 (9) | −0.0047 (9) |
C20 | 0.0286 (10) | 0.0226 (9) | 0.0317 (11) | 0.0015 (7) | 0.0103 (8) | 0.0006 (8) |
C18 | 0.0294 (10) | 0.0269 (10) | 0.0303 (11) | −0.0005 (8) | 0.0075 (8) | −0.0003 (8) |
C17 | 0.0335 (12) | 0.0439 (13) | 0.0342 (13) | −0.0052 (10) | 0.0077 (10) | −0.0094 (11) |
C9 | 0.0482 (14) | 0.0319 (11) | 0.0442 (14) | 0.0011 (10) | 0.0280 (12) | 0.0001 (10) |
C1 | 0.0413 (13) | 0.0330 (12) | 0.0409 (14) | 0.0032 (10) | 0.0084 (11) | 0.0054 (10) |
C16 | 0.0404 (12) | 0.0364 (12) | 0.0340 (12) | 0.0085 (10) | 0.0162 (10) | 0.0053 (10) |
C2 | 0.0321 (11) | 0.0290 (10) | 0.0345 (12) | 0.0004 (8) | 0.0128 (9) | 0.0009 (9) |
C13 | 0.0456 (13) | 0.0293 (11) | 0.0439 (14) | 0.0009 (10) | 0.0129 (11) | 0.0064 (10) |
C24 | 0.0358 (12) | 0.0380 (12) | 0.0449 (14) | −0.0016 (10) | 0.0196 (11) | 0.0000 (10) |
C8 | 0.0420 (13) | 0.0432 (13) | 0.0406 (14) | −0.0123 (10) | 0.0214 (11) | −0.0128 (11) |
C5 | 0.0428 (13) | 0.0389 (13) | 0.0424 (14) | 0.0046 (10) | 0.0050 (11) | −0.0011 (11) |
C14 | 0.0511 (14) | 0.0414 (13) | 0.0371 (14) | −0.0074 (11) | 0.0128 (11) | 0.0104 (11) |
C23 | 0.0563 (15) | 0.0412 (13) | 0.0387 (14) | 0.0027 (11) | 0.0234 (12) | −0.0052 (11) |
C15 | 0.0414 (13) | 0.0496 (14) | 0.0327 (13) | −0.0013 (10) | 0.0174 (10) | 0.0039 (11) |
C6 | 0.0413 (14) | 0.0648 (18) | 0.0422 (15) | 0.0103 (13) | 0.0022 (11) | 0.0042 (13) |
C7 | 0.0347 (13) | 0.0688 (18) | 0.0366 (14) | −0.0095 (12) | 0.0085 (11) | −0.0141 (13) |
C22 | 0.0478 (14) | 0.0380 (12) | 0.0304 (13) | −0.0014 (10) | 0.0057 (11) | −0.0077 (10) |
C25 | 0.0496 (14) | 0.0457 (14) | 0.0431 (15) | −0.0056 (11) | 0.0130 (12) | 0.0100 (12) |
N10 | 0.0902 (17) | 0.0549 (13) | 0.0561 (15) | −0.0215 (12) | 0.0391 (13) | −0.0067 (12) |
C26 | 0.0539 (16) | 0.0614 (17) | 0.0494 (16) | −0.0095 (13) | 0.0228 (13) | −0.0008 (14) |
N11 | 0.117 (2) | 0.0713 (18) | 0.106 (2) | −0.0270 (17) | 0.0595 (18) | −0.0286 (17) |
N12 | 0.0999 (19) | 0.0655 (15) | 0.0540 (15) | −0.0050 (14) | 0.0372 (14) | −0.0008 (13) |
O1 | 0.0715 (12) | 0.0872 (14) | 0.0622 (12) | 0.0390 (11) | 0.0086 (9) | −0.0226 (11) |
Ni1—N1 | 2.1458 (18) | N4—H4A | 0.82 (2) |
Ni1—N2 | 2.0874 (16) | N4—H4B | 0.87 (2) |
Ni1—N4 | 2.1376 (19) | N3—H3A | 0.856 (9) |
Ni1—N5 | 2.0724 (16) | C3—C8 | 1.392 (3) |
Ni1—N7 | 2.0945 (16) | C18—C17 | 1.488 (3) |
Ni1—N9 | 2.1502 (19) | C17—H17D | 0.99 (2) |
N5—C2 | 1.329 (2) | C17—H17C | 0.99 (2) |
N5—C4 | 1.392 (2) | C9—H9A | 0.96 (2) |
N2—C10 | 1.318 (2) | C9—H9B | 0.96 (2) |
N2—C11 | 1.395 (2) | C1—C2 | 1.498 (3) |
N8—C18 | 1.346 (2) | C1—H1D | 0.94 (2) |
N8—C19 | 1.384 (2) | C1—H1C | 0.93 (2) |
N8—H8A | 0.88 (2) | C16—C15 | 1.368 (3) |
N7—C18 | 1.320 (2) | C16—H16 | 0.886 (18) |
N7—C20 | 1.389 (2) | C13—C14 | 1.376 (3) |
N1—C9 | 1.468 (3) | C13—H13 | 0.95 (2) |
N1—H1A | 0.86 (2) | C24—C23 | 1.372 (3) |
N1—H1B | 0.88 (2) | C24—H24 | 0.897 (18) |
N6—C2 | 1.345 (2) | C8—C7 | 1.372 (3) |
N6—C3 | 1.384 (2) | C8—H8 | 0.96 (2) |
C10—N3 | 1.341 (2) | C5—C6 | 1.376 (3) |
C10—C9 | 1.489 (3) | C5—H5 | 0.928 (19) |
N9—C17 | 1.462 (3) | C14—C15 | 1.391 (3) |
N9—H9D | 0.78 (2) | C14—H14 | 0.87 (2) |
N9—H9C | 0.88 (3) | C23—C22 | 1.398 (3) |
C19—C24 | 1.388 (3) | C23—H23 | 0.923 (19) |
C19—C20 | 1.405 (2) | C15—H15 | 0.925 (19) |
C11—C16 | 1.391 (3) | C6—C7 | 1.387 (4) |
C11—C12 | 1.395 (3) | C6—H6 | 0.87 (3) |
C12—N3 | 1.384 (3) | C7—H7 | 0.88 (2) |
C12—C13 | 1.383 (3) | C22—H22 | 0.87 (2) |
C4—C5 | 1.392 (3) | C25—N10 | 1.301 (3) |
C4—C3 | 1.408 (3) | C25—N12 | 1.143 (3) |
C21—C22 | 1.366 (3) | C26—N10 | 1.283 (3) |
C21—C20 | 1.393 (3) | C26—N11 | 1.142 (3) |
C21—H21 | 0.921 (18) | O1—H101 | 0.8490 |
N4—C1 | 1.464 (3) | O1—H100 | 0.8501 |
N1—Ni1—N2 | 79.30 (7) | N6—C3—C8 | 131.0 (2) |
N1—Ni1—N4 | 92.69 (8) | N6—C3—C4 | 108.28 (17) |
N1—Ni1—N5 | 95.61 (7) | C8—C3—C4 | 120.7 (2) |
N1—Ni1—N7 | 168.66 (7) | N7—C20—C21 | 131.10 (17) |
N1—Ni1—N9 | 89.66 (8) | N7—C20—C19 | 108.66 (16) |
N2—Ni1—N4 | 171.96 (7) | C21—C20—C19 | 120.10 (18) |
N2—Ni1—N5 | 102.57 (7) | N7—C18—N8 | 114.00 (17) |
N2—Ni1—N7 | 97.18 (6) | N7—C18—C17 | 121.82 (17) |
N2—Ni1—N9 | 88.98 (8) | N8—C18—C17 | 124.19 (18) |
N4—Ni1—N5 | 78.74 (7) | N9—C17—C18 | 108.87 (18) |
N4—Ni1—N7 | 90.56 (8) | N9—C17—H17D | 111.9 (12) |
N4—Ni1—N9 | 90.29 (9) | C18—C17—H17D | 111.8 (12) |
N5—Ni1—N7 | 95.68 (6) | N9—C17—H17C | 112.7 (12) |
N5—Ni1—N9 | 168.01 (7) | C18—C17—H17C | 107.1 (12) |
N7—Ni1—N9 | 79.45 (7) | H17D—C17—H17C | 104.4 (16) |
C2—N5—C4 | 103.73 (16) | N1—C9—C10 | 109.45 (17) |
C2—N5—Ni1 | 113.36 (13) | N1—C9—H9A | 113.3 (14) |
C4—N5—Ni1 | 142.76 (13) | C10—C9—H9A | 109.4 (14) |
C10—N2—C11 | 104.99 (16) | N1—C9—H9B | 108.3 (14) |
C10—N2—Ni1 | 113.14 (13) | C10—C9—H9B | 108.2 (13) |
C11—N2—Ni1 | 140.19 (12) | H9A—C9—H9B | 108.1 (18) |
C18—N8—C19 | 106.09 (16) | N4—C1—C2 | 108.54 (18) |
C18—N8—H8A | 120.5 (15) | N4—C1—H1D | 107.9 (13) |
C19—N8—H8A | 130.3 (15) | C2—C1—H1D | 109.7 (13) |
C18—N7—C20 | 105.02 (15) | N4—C1—H1C | 110.6 (13) |
C18—N7—Ni1 | 112.90 (12) | C2—C1—H1C | 110.4 (12) |
C20—N7—Ni1 | 141.52 (12) | H1D—C1—H1C | 109.6 (17) |
C9—N1—Ni1 | 112.01 (13) | C15—C16—C11 | 117.8 (2) |
C9—N1—H1A | 107.0 (14) | C15—C16—H16 | 120.6 (12) |
Ni1—N1—H1A | 112.5 (14) | C11—C16—H16 | 121.6 (12) |
C9—N1—H1B | 110.6 (14) | N5—C2—N6 | 116.45 (18) |
Ni1—N1—H1B | 106.6 (13) | N5—C2—C1 | 119.70 (18) |
H1A—N1—H1B | 108 (2) | N6—C2—C1 | 123.85 (18) |
C2—N6—C3 | 103.51 (16) | C14—C13—C12 | 116.2 (2) |
N2—C10—N3 | 113.29 (17) | C14—C13—H13 | 123.1 (13) |
N2—C10—C9 | 122.44 (18) | C12—C13—H13 | 120.6 (13) |
N3—C10—C9 | 124.22 (18) | C23—C24—C19 | 116.7 (2) |
C17—N9—Ni1 | 110.75 (13) | C23—C24—H24 | 123.1 (12) |
C17—N9—H9D | 110.2 (17) | C19—C24—H24 | 120.2 (12) |
Ni1—N9—H9D | 111.1 (16) | C7—C8—C3 | 117.7 (2) |
C17—N9—H9C | 110.9 (16) | C7—C8—H8 | 121.7 (12) |
Ni1—N9—H9C | 107.0 (16) | C3—C8—H8 | 120.6 (12) |
H9D—N9—H9C | 107 (2) | C6—C5—C4 | 117.4 (2) |
N8—C19—C24 | 131.63 (19) | C6—C5—H5 | 122.3 (13) |
N8—C19—C20 | 106.22 (17) | C4—C5—H5 | 120.2 (13) |
C24—C19—C20 | 122.05 (19) | C13—C14—C15 | 122.2 (2) |
C16—C11—C12 | 120.11 (18) | C13—C14—H14 | 118.1 (15) |
C16—C11—N2 | 130.78 (18) | C15—C14—H14 | 119.7 (15) |
C12—C11—N2 | 109.10 (16) | C24—C23—C22 | 121.7 (2) |
N3—C12—C13 | 132.08 (19) | C24—C23—H23 | 119.0 (12) |
N3—C12—C11 | 105.51 (16) | C22—C23—H23 | 119.4 (12) |
C13—C12—C11 | 122.41 (19) | C16—C15—C14 | 121.3 (2) |
N5—C4—C5 | 131.17 (19) | C16—C15—H15 | 117.9 (13) |
N5—C4—C3 | 108.03 (17) | C14—C15—H15 | 120.7 (13) |
C5—C4—C3 | 120.76 (19) | C5—C6—C7 | 121.7 (2) |
C22—C21—C20 | 117.6 (2) | C5—C6—H6 | 117.9 (18) |
C22—C21—H21 | 122.1 (12) | C7—C6—H6 | 120.3 (18) |
C20—C21—H21 | 120.3 (12) | C8—C7—C6 | 121.7 (2) |
C1—N4—Ni1 | 108.91 (14) | C8—C7—H7 | 120.9 (15) |
C1—N4—H4A | 111.1 (15) | C6—C7—H7 | 117.4 (15) |
Ni1—N4—H4A | 115.4 (15) | C21—C22—C23 | 121.9 (2) |
C1—N4—H4B | 108.0 (14) | C21—C22—H22 | 119.7 (13) |
Ni1—N4—H4B | 103.5 (14) | C23—C22—H22 | 118.4 (13) |
H4A—N4—H4B | 109 (2) | N12—C25—N10 | 173.6 (3) |
C10—N3—C12 | 107.12 (16) | C26—N10—C25 | 122.2 (2) |
C10—N3—H3A | 124.8 (15) | N11—C26—N10 | 173.4 (3) |
C12—N3—H3A | 128.0 (15) | H101—O1—H100 | 127.3 |
D—H···A | D—H | H···A | D···A | D—H···A |
N1—H1B···N12i | 0.88 (2) | 2.45 (2) | 3.270 (4) | 155.0 (18) |
N1—H1A···O1ii | 0.86 (2) | 2.32 (2) | 3.119 (3) | 154.8 (19) |
N3—H3A···O1 | 0.86 (1) | 2.02 (1) | 2.853 (2) | 166 (2) |
N4—H4B···N10 | 0.87 (2) | 2.35 (2) | 3.184 (3) | 161.1 (18) |
N8—H8A···N6iii | 0.88 (2) | 1.91 (2) | 2.762 (2) | 163 (2) |
N9—H9D···N12i | 0.78 (2) | 2.30 (2) | 3.044 (3) | 160 (2) |
O1—H100···N11iv | 0.85 | 2.17 | 2.851 (3) | 137 |
O1—H101···N6iv | 0.85 | 2.51 | 3.179 (3) | 136 |
Symmetry codes: (i) −x, −y, −z; (ii) −x+1/2, y+1/2, −z+1/2; (iii) −x−1/2, y−1/2, −z+1/2; (iv) x, y−1, z. |