In the title compound, [Ni(C22H34N6)](ClO4)2, the 14-membered hexaazacyclotetradecane macrocycle chelates to the Ni atom through its four secondary N atoms. The asymmetric unit contains two independent half-molecules, with the Ni atoms located on inversion centers. The Ni atoms have a distorted octahedral geometry, with long Ni-O(perchlorate) bonds. The occurrence of hydrogen-bonding interactions results in a linear chain structure.
Supporting information
CCDC reference: 205547
Key indicators
- Single-crystal X-ray study
- T = 298 K
- Mean (C-C) = 0.004 Å
- R factor = 0.036
- wR factor = 0.105
- Data-to-parameter ratio = 17.2
checkCIF/PLATON results
No syntax errors found
Alert level C
PLAT029_ALERT_3_C _diffrn_measured_fraction_theta_full Low ....... 0.97
PLAT042_ALERT_1_C Calc. and Rep. MoietyFormula Strings Differ .... ?
0 ALERT level A = In general: serious problem
0 ALERT level B = Potentially serious problem
2 ALERT level C = Check and explain
0 ALERT level G = General alerts; check
1 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
0 ALERT type 2 Indicator that the structure model may be wrong or deficient
1 ALERT type 3 Indicator that the structure quality may be low
0 ALERT type 4 Improvement, methodology, query or suggestion
Data collection: SMART (Bruker, 1999); cell refinement: SAINT (Bruker, 1999); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEPIII (Burnett & Johnson, 1996), ORTEP-3 for Windows
(Farrugia, 1997) and PLUTON (Spek, 1990); software used to prepare material for publication: SHELXL97.
[1,8-Bis(2-benzyl)-1,3,6,8,10,13-hexaazacyclotetradecane]nickel(II)
diperchlorate
top
Crystal data top
[Ni(C22H34N6)](ClO4)2 | Z = 2 |
Mr = 640.16 | F(000) = 668 |
Triclinic, P1 | Dx = 1.552 Mg m−3 |
Hall symbol: -P 1 | Mo Kα radiation, λ = 0.71073 Å |
a = 10.209 (1) Å | Cell parameters from 855 reflections |
b = 11.617 (1) Å | θ = 4.0–29.8° |
c = 11.916 (1) Å | µ = 0.96 mm−1 |
α = 87.633 (2)° | T = 298 K |
β = 75.940 (2)° | Prism, yellow |
γ = 88.501 (2)° | 0.23 × 0.22 × 0.12 mm |
V = 1369.5 (2) Å3 | |
Data collection top
Bruker SMART 1K area-detector diffractometer | 6134 independent reflections |
Radiation source: normal-focus sealed tube | 5089 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.011 |
Detector resolution: 8.33 pixels mm-1 | θmax = 27.5°, θmin = 4.1° |
φ and ω scans | h = −13→9 |
Absorption correction: multi-scan SADABS (Sheldrick, 1996) | k = −15→12 |
Tmin = 0.809, Tmax = 0.893 | l = −15→12 |
8366 measured reflections | |
Refinement top
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)] = 0.036 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.105 | H-atom parameters constrained |
S = 1.05 | w = 1/[σ2(Fo2) + (0.0591P)2 + 0.4245P] where P = (Fo2 + 2Fc2)/3 |
6134 reflections | (Δ/σ)max = 0.001 |
357 parameters | Δρmax = 0.66 e Å−3 |
96 restraints | Δρmin = −0.51 e Å−3 |
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. |
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top | x | y | z | Uiso*/Ueq | |
Ni1 | 0.5000 | 0.5000 | 0.5000 | 0.02862 (10) | |
Ni2 | 0.5000 | 0.0000 | 0.0000 | 0.02726 (10) | |
C1 | 0.5635 (3) | 0.5956 (2) | 0.7049 (2) | 0.0451 (5) | |
H1A | 0.5782 | 0.6711 | 0.6666 | 0.054* | |
H1B | 0.5305 | 0.6068 | 0.7872 | 0.054* | |
C2 | 0.3270 (3) | 0.6017 (2) | 0.6905 (2) | 0.0454 (5) | |
H2A | 0.3417 | 0.6824 | 0.6679 | 0.054* | |
H2B | 0.2864 | 0.5957 | 0.7730 | 0.054* | |
C3 | 0.2370 (2) | 0.5499 (2) | 0.6242 (2) | 0.0456 (5) | |
H3A | 0.2105 | 0.4733 | 0.6554 | 0.055* | |
H3B | 0.1561 | 0.5971 | 0.6294 | 0.055* | |
C4 | 0.2433 (2) | 0.4740 (2) | 0.4340 (2) | 0.0425 (5) | |
H4A | 0.2322 | 0.3969 | 0.4691 | 0.051* | |
H4B | 0.1539 | 0.5072 | 0.4397 | 0.051* | |
C5 | 0.3153 (2) | 0.5733 (2) | 0.2428 (2) | 0.0432 (5) | |
H5A | 0.3691 | 0.5593 | 0.1653 | 0.052* | |
H5B | 0.3600 | 0.6317 | 0.2751 | 0.052* | |
C6 | 0.1781 (2) | 0.6184 (2) | 0.23504 (19) | 0.0406 (5) | |
C7 | 0.1166 (3) | 0.5790 (2) | 0.1530 (2) | 0.0539 (6) | |
H7 | 0.1585 | 0.5212 | 0.1046 | 0.065* | |
C8 | −0.0066 (3) | 0.6247 (3) | 0.1421 (3) | 0.0657 (8) | |
H8 | −0.0457 | 0.5992 | 0.0850 | 0.079* | |
C9 | −0.0713 (3) | 0.7080 (3) | 0.2158 (3) | 0.0634 (8) | |
H9 | −0.1548 | 0.7377 | 0.2094 | 0.076* | |
C10 | −0.0127 (3) | 0.7469 (3) | 0.2980 (3) | 0.0606 (7) | |
H10 | −0.0564 | 0.8030 | 0.3480 | 0.073* | |
C11 | 0.1121 (3) | 0.7029 (2) | 0.3073 (2) | 0.0511 (6) | |
H11 | 0.1519 | 0.7306 | 0.3629 | 0.061* | |
C12 | 0.2410 (2) | −0.1159 (2) | 0.0301 (2) | 0.0429 (5) | |
H12A | 0.2788 | −0.1878 | 0.0536 | 0.052* | |
H12B | 0.1459 | −0.1135 | 0.0691 | 0.052* | |
C13 | 0.2878 (2) | −0.0234 (2) | 0.19751 (17) | 0.0395 (5) | |
H13A | 0.3083 | −0.1004 | 0.2239 | 0.047* | |
H13B | 0.1945 | −0.0044 | 0.2343 | 0.047* | |
C14 | 0.3805 (2) | 0.0622 (2) | 0.22703 (18) | 0.0398 (5) | |
H14A | 0.3513 | 0.1402 | 0.2118 | 0.048* | |
H14B | 0.3814 | 0.0536 | 0.3082 | 0.048* | |
C15 | 0.6124 (2) | 0.13189 (19) | 0.1601 (2) | 0.0385 (5) | |
H15A | 0.5768 | 0.2044 | 0.1358 | 0.046* | |
H15B | 0.6155 | 0.1377 | 0.2404 | 0.046* | |
C16 | 0.8320 (2) | 0.0343 (2) | 0.1414 (2) | 0.0421 (5) | |
H16A | 0.9017 | 0.0025 | 0.0795 | 0.051* | |
H16B | 0.7778 | −0.0289 | 0.1820 | 0.051* | |
C17 | 0.8971 (2) | 0.0935 (2) | 0.2244 (2) | 0.0390 (5) | |
C18 | 0.8651 (3) | 0.0638 (2) | 0.3413 (2) | 0.0514 (6) | |
H18 | 0.8008 | 0.0080 | 0.3704 | 0.062* | |
C19 | 0.9289 (3) | 0.1170 (3) | 0.4158 (3) | 0.0646 (8) | |
H19 | 0.9072 | 0.0964 | 0.4943 | 0.078* | |
C20 | 1.0231 (3) | 0.1992 (3) | 0.3740 (3) | 0.0645 (8) | |
H20 | 1.0661 | 0.2338 | 0.4240 | 0.077* | |
C21 | 1.0545 (3) | 0.2312 (3) | 0.2588 (3) | 0.0596 (7) | |
H21 | 1.1180 | 0.2880 | 0.2308 | 0.071* | |
C22 | 0.9916 (2) | 0.1787 (2) | 0.1839 (2) | 0.0496 (6) | |
H22 | 1.0129 | 0.2009 | 0.1058 | 0.059* | |
N1 | 0.45669 (19) | 0.53585 (15) | 0.66207 (15) | 0.0349 (4) | |
H1 | 0.4418 | 0.4674 | 0.7027 | 0.042* | |
N2 | 0.31535 (17) | 0.54460 (15) | 0.50175 (15) | 0.0342 (4) | |
H2 | 0.3177 | 0.6178 | 0.4710 | 0.041* | |
N3 | 0.3102 (2) | 0.46581 (16) | 0.31442 (16) | 0.0411 (4) | |
N4 | 0.30957 (17) | −0.01765 (15) | 0.06928 (14) | 0.0323 (4) | |
H4 | 0.2676 | 0.0481 | 0.0511 | 0.039* | |
N5 | 0.51754 (17) | 0.03758 (15) | 0.15204 (14) | 0.0321 (4) | |
H5 | 0.5488 | −0.0275 | 0.1828 | 0.039* | |
N6 | 0.74627 (19) | 0.11509 (16) | 0.09187 (16) | 0.0391 (4) | |
Cl1 | 0.53145 (6) | 0.81334 (4) | 0.42677 (5) | 0.04294 (14) | |
O11 | 0.5861 (2) | 0.90013 (18) | 0.34389 (19) | 0.0719 (6) | |
O12 | 0.5997 (3) | 0.70582 (17) | 0.4011 (2) | 0.0792 (7) | |
O13 | 0.3930 (2) | 0.7962 (2) | 0.4239 (3) | 0.0947 (8) | |
O14 | 0.5366 (5) | 0.8438 (2) | 0.5369 (2) | 0.1286 (13) | |
Cl2 | 0.36834 (6) | 0.29594 (5) | −0.04832 (5) | 0.04134 (14) | |
O21 | 0.3469 (2) | 0.39121 (17) | −0.12005 (19) | 0.0674 (6) | |
O22 | 0.4846 (3) | 0.2315 (2) | −0.1008 (3) | 0.1066 (10) | |
O23 | 0.2580 (2) | 0.2180 (2) | −0.0296 (3) | 0.1031 (10) | |
O24 | 0.3812 (6) | 0.3315 (3) | 0.0565 (3) | 0.1586 (18) | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
Ni1 | 0.03381 (19) | 0.02616 (18) | 0.02739 (18) | 0.00008 (13) | −0.01048 (14) | −0.00026 (13) |
Ni2 | 0.03079 (18) | 0.02865 (18) | 0.02325 (17) | −0.00063 (13) | −0.00834 (13) | −0.00073 (13) |
C1 | 0.0639 (15) | 0.0354 (11) | 0.0433 (12) | 0.0033 (10) | −0.0263 (11) | −0.0074 (9) |
C2 | 0.0537 (14) | 0.0440 (12) | 0.0371 (12) | 0.0139 (10) | −0.0091 (10) | −0.0055 (9) |
C3 | 0.0391 (12) | 0.0507 (14) | 0.0435 (13) | 0.0060 (10) | −0.0046 (10) | 0.0022 (10) |
C4 | 0.0441 (12) | 0.0406 (12) | 0.0474 (13) | −0.0105 (10) | −0.0208 (10) | 0.0098 (10) |
C5 | 0.0476 (13) | 0.0437 (12) | 0.0423 (12) | −0.0040 (10) | −0.0196 (10) | 0.0080 (10) |
C6 | 0.0441 (12) | 0.0413 (12) | 0.0386 (11) | −0.0057 (9) | −0.0153 (10) | 0.0107 (9) |
C7 | 0.0617 (16) | 0.0541 (15) | 0.0526 (15) | 0.0000 (12) | −0.0269 (13) | −0.0011 (12) |
C8 | 0.0622 (17) | 0.076 (2) | 0.0698 (19) | −0.0096 (15) | −0.0391 (16) | 0.0094 (16) |
C9 | 0.0471 (15) | 0.0679 (18) | 0.076 (2) | 0.0012 (13) | −0.0220 (14) | 0.0231 (16) |
C10 | 0.0614 (17) | 0.0567 (16) | 0.0603 (17) | 0.0099 (13) | −0.0107 (14) | 0.0065 (13) |
C11 | 0.0594 (15) | 0.0479 (14) | 0.0496 (14) | −0.0007 (11) | −0.0210 (12) | 0.0018 (11) |
C12 | 0.0432 (12) | 0.0473 (13) | 0.0403 (12) | −0.0128 (10) | −0.0138 (10) | 0.0060 (10) |
C13 | 0.0388 (11) | 0.0515 (13) | 0.0257 (10) | −0.0024 (9) | −0.0032 (8) | 0.0013 (9) |
C14 | 0.0389 (11) | 0.0509 (13) | 0.0289 (10) | 0.0037 (10) | −0.0061 (9) | −0.0085 (9) |
C15 | 0.0421 (11) | 0.0368 (11) | 0.0415 (12) | 0.0007 (9) | −0.0188 (10) | −0.0085 (9) |
C16 | 0.0392 (11) | 0.0469 (13) | 0.0436 (12) | 0.0027 (9) | −0.0157 (10) | −0.0064 (10) |
C17 | 0.0330 (10) | 0.0456 (12) | 0.0412 (12) | 0.0038 (9) | −0.0142 (9) | −0.0032 (9) |
C18 | 0.0556 (15) | 0.0543 (15) | 0.0448 (13) | −0.0048 (12) | −0.0130 (11) | 0.0011 (11) |
C19 | 0.082 (2) | 0.0737 (19) | 0.0430 (14) | 0.0038 (16) | −0.0240 (14) | −0.0062 (13) |
C20 | 0.0671 (18) | 0.0682 (19) | 0.072 (2) | 0.0038 (15) | −0.0405 (16) | −0.0226 (15) |
C21 | 0.0443 (14) | 0.0572 (16) | 0.081 (2) | −0.0081 (12) | −0.0218 (14) | −0.0059 (14) |
C22 | 0.0427 (13) | 0.0574 (15) | 0.0497 (14) | −0.0058 (11) | −0.0142 (11) | 0.0050 (11) |
N1 | 0.0457 (10) | 0.0306 (9) | 0.0297 (8) | 0.0041 (7) | −0.0122 (8) | −0.0001 (7) |
N2 | 0.0369 (9) | 0.0321 (9) | 0.0346 (9) | −0.0006 (7) | −0.0113 (7) | 0.0039 (7) |
N3 | 0.0516 (11) | 0.0374 (10) | 0.0404 (10) | −0.0036 (8) | −0.0233 (9) | 0.0031 (8) |
N4 | 0.0330 (9) | 0.0360 (9) | 0.0288 (8) | −0.0009 (7) | −0.0096 (7) | 0.0023 (7) |
N5 | 0.0362 (9) | 0.0332 (9) | 0.0289 (8) | 0.0018 (7) | −0.0119 (7) | −0.0017 (7) |
N6 | 0.0390 (9) | 0.0441 (10) | 0.0386 (10) | −0.0033 (8) | −0.0177 (8) | −0.0028 (8) |
Cl1 | 0.0632 (4) | 0.0310 (3) | 0.0349 (3) | −0.0052 (2) | −0.0128 (2) | 0.0043 (2) |
O11 | 0.0920 (15) | 0.0579 (12) | 0.0685 (13) | −0.0242 (11) | −0.0276 (12) | 0.0324 (10) |
O12 | 0.0881 (16) | 0.0418 (11) | 0.1023 (18) | 0.0110 (10) | −0.0145 (14) | −0.0004 (11) |
O13 | 0.0630 (14) | 0.0772 (16) | 0.142 (3) | −0.0115 (12) | −0.0235 (15) | 0.0178 (16) |
O14 | 0.260 (4) | 0.088 (2) | 0.0543 (15) | −0.015 (2) | −0.068 (2) | −0.0070 (13) |
Cl2 | 0.0473 (3) | 0.0423 (3) | 0.0358 (3) | 0.0040 (2) | −0.0140 (2) | 0.0042 (2) |
O21 | 0.0668 (12) | 0.0590 (12) | 0.0768 (14) | 0.0002 (10) | −0.0235 (11) | 0.0301 (10) |
O22 | 0.0846 (17) | 0.0700 (16) | 0.136 (2) | 0.0284 (14) | 0.0227 (16) | 0.0227 (15) |
O23 | 0.0710 (15) | 0.0916 (18) | 0.148 (3) | −0.0240 (13) | −0.0394 (16) | 0.0666 (17) |
O24 | 0.313 (6) | 0.112 (2) | 0.086 (2) | 0.020 (3) | −0.116 (3) | −0.0286 (18) |
Geometric parameters (Å, º) top
Ni1—N1 | 1.9340 (17) | C13—N4 | 1.489 (3) |
Ni1—N2 | 1.9372 (17) | C13—C14 | 1.500 (3) |
Ni1—O12 | 2.730 (2) | C13—H13A | 0.9700 |
Ni2—N4 | 1.9314 (17) | C13—H13B | 0.9700 |
Ni2—N5 | 1.9318 (16) | C14—N5 | 1.494 (3) |
Ni2—O22 | 2.916 (2) | C14—H14A | 0.9700 |
C1—N3i | 1.431 (3) | C14—H14B | 0.9700 |
C1—N1 | 1.506 (3) | C15—N6 | 1.424 (3) |
C1—H1A | 0.9700 | C15—N5 | 1.502 (3) |
C1—H1B | 0.9700 | C15—H15A | 0.9700 |
C2—N1 | 1.484 (3) | C15—H15B | 0.9700 |
C2—C3 | 1.501 (4) | C16—N6 | 1.469 (3) |
C2—H2A | 0.9700 | C16—C17 | 1.514 (3) |
C2—H2B | 0.9700 | C16—H16A | 0.9700 |
C3—N2 | 1.487 (3) | C16—H16B | 0.9700 |
C3—H3A | 0.9700 | C17—C18 | 1.383 (3) |
C3—H3B | 0.9700 | C17—C22 | 1.388 (3) |
C4—N3 | 1.429 (3) | C18—C19 | 1.393 (4) |
C4—N2 | 1.497 (3) | C18—H18 | 0.9300 |
C4—H4A | 0.9700 | C19—C20 | 1.364 (5) |
C4—H4B | 0.9700 | C19—H19 | 0.9300 |
C5—N3 | 1.478 (3) | C20—C21 | 1.370 (4) |
C5—C6 | 1.506 (3) | C20—H20 | 0.9300 |
C5—H5A | 0.9700 | C21—C22 | 1.387 (4) |
C5—H5B | 0.9700 | C21—H21 | 0.9300 |
C6—C7 | 1.381 (3) | C22—H22 | 0.9300 |
C6—C11 | 1.382 (4) | N1—H1 | 0.9100 |
C7—C8 | 1.386 (4) | N2—H2 | 0.9100 |
C7—H7 | 0.9300 | N3—C1i | 1.431 (3) |
C8—C9 | 1.378 (5) | N4—H4 | 0.9100 |
C8—H8 | 0.9300 | N5—H5 | 0.9100 |
C9—C10 | 1.363 (4) | N6—C12ii | 1.427 (3) |
C9—H9 | 0.9300 | Cl1—O14 | 1.387 (2) |
C10—C11 | 1.388 (4) | Cl1—O11 | 1.4082 (18) |
C10—H10 | 0.9300 | Cl1—O12 | 1.422 (2) |
C11—H11 | 0.9300 | Cl1—O13 | 1.441 (2) |
C12—N6ii | 1.427 (3) | Cl2—O24 | 1.369 (3) |
C12—N4 | 1.502 (3) | Cl2—O22 | 1.411 (2) |
C12—H12A | 0.9700 | Cl2—O21 | 1.4156 (18) |
C12—H12B | 0.9700 | Cl2—O23 | 1.433 (2) |
| | | |
N1—Ni1—N2 | 86.66 (7) | N5—C14—H14B | 110.5 |
N1i—Ni1—N2 | 93.34 (7) | C13—C14—H14B | 110.5 |
N1—Ni1—O12 | 100.60 (8) | H14A—C14—H14B | 108.7 |
N1i—Ni1—O12 | 79.40 (8) | N6—C15—N5 | 113.97 (17) |
N2—Ni1—O12 | 93.11 (7) | N6—C15—H15A | 108.8 |
N2i—Ni1—O12 | 86.89 (7) | N5—C15—H15A | 108.8 |
N4—Ni2—N5 | 86.70 (7) | N6—C15—H15B | 108.8 |
N4ii—Ni2—N5 | 93.30 (7) | N5—C15—H15B | 108.8 |
N4—Ni2—O22 | 97.51 (7) | H15A—C15—H15B | 107.7 |
N4ii—Ni2—O22 | 82.49 (7) | N6—C16—C17 | 111.14 (18) |
N5—Ni2—O22 | 99.83 (9) | N6—C16—H16A | 109.4 |
N5ii—Ni2—O22 | 80.17 (9) | C17—C16—H16A | 109.4 |
N3i—C1—N1 | 113.94 (17) | N6—C16—H16B | 109.4 |
N3i—C1—H1A | 108.8 | C17—C16—H16B | 109.4 |
N1—C1—H1A | 108.8 | H16A—C16—H16B | 108.0 |
N3i—C1—H1B | 108.8 | C18—C17—C22 | 118.5 (2) |
N1—C1—H1B | 108.8 | C18—C17—C16 | 121.1 (2) |
H1A—C1—H1B | 107.7 | C22—C17—C16 | 120.3 (2) |
N1—C2—C3 | 106.59 (18) | C17—C18—C19 | 120.3 (3) |
N1—C2—H2A | 110.4 | C17—C18—H18 | 119.9 |
C3—C2—H2A | 110.4 | C19—C18—H18 | 119.9 |
N1—C2—H2B | 110.4 | C20—C19—C18 | 120.2 (3) |
C3—C2—H2B | 110.4 | C20—C19—H19 | 119.9 |
H2A—C2—H2B | 108.6 | C18—C19—H19 | 119.9 |
N2—C3—C2 | 107.05 (19) | C19—C20—C21 | 120.3 (3) |
N2—C3—H3A | 110.3 | C19—C20—H20 | 119.8 |
C2—C3—H3A | 110.3 | C21—C20—H20 | 119.8 |
N2—C3—H3B | 110.3 | C20—C21—C22 | 119.9 (3) |
C2—C3—H3B | 110.3 | C20—C21—H21 | 120.1 |
H3A—C3—H3B | 108.6 | C22—C21—H21 | 120.1 |
N3—C4—N2 | 114.45 (18) | C21—C22—C17 | 120.7 (2) |
N3—C4—H4A | 108.6 | C21—C22—H22 | 119.6 |
N2—C4—H4A | 108.6 | C17—C22—H22 | 119.6 |
N3—C4—H4B | 108.6 | C2—N1—C1 | 110.69 (17) |
N2—C4—H4B | 108.6 | C2—N1—Ni1 | 109.20 (13) |
H4A—C4—H4B | 107.6 | C1—N1—Ni1 | 116.87 (14) |
N3—C5—C6 | 113.32 (19) | C2—N1—H1 | 106.5 |
N3—C5—H5A | 108.9 | C1—N1—H1 | 106.5 |
C6—C5—H5A | 108.9 | Ni1—N1—H1 | 106.5 |
N3—C5—H5B | 108.9 | C3—N2—C4 | 110.50 (18) |
C6—C5—H5B | 108.9 | C3—N2—Ni1 | 108.53 (14) |
H5A—C5—H5B | 107.7 | C4—N2—Ni1 | 117.16 (14) |
C7—C6—C11 | 118.2 (2) | C3—N2—H2 | 106.7 |
C7—C6—C5 | 120.8 (2) | C4—N2—H2 | 106.7 |
C11—C6—C5 | 121.0 (2) | Ni1—N2—H2 | 106.7 |
C6—C7—C8 | 120.8 (3) | C4—N3—C1i | 113.60 (18) |
C6—C7—H7 | 119.6 | C4—N3—C5 | 116.03 (19) |
C8—C7—H7 | 119.6 | C1i—N3—C5 | 113.48 (19) |
C9—C8—C7 | 120.0 (3) | C13—N4—C12 | 110.37 (16) |
C9—C8—H8 | 120.0 | C13—N4—Ni2 | 108.90 (12) |
C7—C8—H8 | 120.0 | C12—N4—Ni2 | 116.98 (14) |
C10—C9—C8 | 119.9 (3) | C13—N4—H4 | 106.7 |
C10—C9—H9 | 120.0 | C12—N4—H4 | 106.7 |
C8—C9—H9 | 120.0 | Ni2—N4—H4 | 106.7 |
C9—C10—C11 | 120.0 (3) | C14—N5—C15 | 110.04 (16) |
C9—C10—H10 | 120.0 | C14—N5—Ni2 | 109.00 (12) |
C11—C10—H10 | 120.0 | C15—N5—Ni2 | 117.86 (13) |
C6—C11—C10 | 121.0 (3) | C14—N5—H5 | 106.4 |
C6—C11—H11 | 119.5 | C15—N5—H5 | 106.4 |
C10—C11—H11 | 119.5 | Ni2—N5—H5 | 106.4 |
N6ii—C12—N4 | 114.05 (18) | C15—N6—C12ii | 115.04 (18) |
N6ii—C12—H12A | 108.7 | C15—N6—C16 | 115.85 (19) |
N4—C12—H12A | 108.7 | C12ii—N6—C16 | 118.18 (19) |
N6ii—C12—H12B | 108.7 | O14—Cl1—O11 | 110.92 (16) |
N4—C12—H12B | 108.7 | O14—Cl1—O12 | 109.43 (18) |
H12A—C12—H12B | 107.6 | O11—Cl1—O12 | 111.66 (15) |
N4—C13—C14 | 106.83 (17) | O14—Cl1—O13 | 109.4 (2) |
N4—C13—H13A | 110.4 | O11—Cl1—O13 | 108.84 (15) |
C14—C13—H13A | 110.4 | O12—Cl1—O13 | 106.45 (16) |
N4—C13—H13B | 110.4 | O24—Cl2—O22 | 109.1 (3) |
C14—C13—H13B | 110.4 | O24—Cl2—O21 | 110.85 (18) |
H13A—C13—H13B | 108.6 | O22—Cl2—O21 | 111.45 (15) |
N5—C14—C13 | 106.27 (17) | O24—Cl2—O23 | 108.9 (3) |
N5—C14—H14A | 110.5 | O22—Cl2—O23 | 105.89 (18) |
C13—C14—H14A | 110.5 | O21—Cl2—O23 | 110.45 (13) |
Symmetry codes: (i) −x+1, −y+1, −z+1; (ii) −x+1, −y, −z. |
Hydrogen-bond geometry (Å, º) top
D—H···A | D—H | H···A | D···A | D—H···A |
N1—H1···O21iii | 0.91 | 2.25 | 3.024 (3) | 142 |
N1—H1···O12i | 0.91 | 2.50 | 3.042 (3) | 118 |
N2—H2···O13 | 0.91 | 2.23 | 3.094 (3) | 158 |
N4—H4···O23 | 0.91 | 2.17 | 3.020 (3) | 155 |
N5—H5···O11iv | 0.91 | 2.18 | 2.947 (3) | 142 |
Symmetry codes: (i) −x+1, −y+1, −z+1; (iii) x, y, z+1; (iv) x, y−1, z. |