In the title complex, [Ni(C14H34N6)](ClO4)2, the 14-membered hexaazacyclotetradecane macrocycle ring chelates to the Ni atom through its four secondary N atoms. The O atoms of the perchlorate ions are 2.86 (1) and 3.070 (4) Å from the Ni atom, whose geometry is best described as intermediate between octahedral and square pyramidal.
Supporting information
CCDC reference: 205546
Key indicators
- Single-crystal X-ray study
- T = 298 K
- Mean (C-C) = 0.006 Å
- Disorder in solvent or counterion
- R factor = 0.044
- wR factor = 0.131
- Data-to-parameter ratio = 12.8
checkCIF/PLATON results
No syntax errors found
Alert level B
PLAT029_ALERT_3_B _diffrn_measured_fraction_theta_full Low ....... 0.96
PLAT430_ALERT_2_B Short Inter D...A Contact O13 .. O24 = 2.76 Ang.
PLAT430_ALERT_2_B Short Inter D...A Contact O23 .. O23 = 2.81 Ang.
Alert level C
PLAT042_ALERT_1_C Calc. and Rep. MoietyFormula Strings Differ .... ?
PLAT152_ALERT_1_C Supplied and Calc Volume s.u. Inconsistent ..... ?
PLAT244_ALERT_4_C Low Solvent U(eq) as Compared to Neighbors .... Cl2
PLAT244_ALERT_4_C Low Solvent U(eq) as Compared to Neighbors .... Cl1
PLAT302_ALERT_4_C Anion/Solvent Disorder ......................... 23.00 Perc.
PLAT480_ALERT_4_C Long H...A H-Bond Reported H2 .. O24 = 2.63 Ang.
0 ALERT level A = In general: serious problem
3 ALERT level B = Potentially serious problem
6 ALERT level C = Check and explain
0 ALERT level G = General alerts; check
2 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
1 ALERT type 3 Indicator that the structure quality may be low
4 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) and ORTEP-3 for Windows (Farrugia, 1997); software used to prepare material for publication: SHELXL97.
[1,8-Di-2-n-propyl-1,3,6,8,10,13-hexaazacyclotetradecane]nickel(II)
diperchlorate
top
Crystal data top
[Ni(C14H34N6)](ClO4)2 | Z = 2 |
Mr = 544.08 | F(000) = 572 |
Triclinic, P1 | Dx = 1.540 Mg m−3 |
Hall symbol: -P 1 | Mo Kα radiation, λ = 0.71073 Å |
a = 8.1634 (6) Å | Cell parameters from 2807 reflections |
b = 12.411 (1) Å | θ = 4.2–29.5° |
c = 12.518 (1) Å | µ = 1.11 mm−1 |
α = 77.094 (1)° | T = 298 K |
β = 83.348 (1)° | Plate, yellow |
γ = 71.882 (1)° | 0.42 × 0.25 × 0.08 mm |
V = 1173.5 (2) Å3 | |
Data collection top
Bruker SMART 1K area-detector diffractometer | 3973 independent reflections |
Radiation source: normal-focus sealed tube | 3155 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.015 |
Detector resolution: 8.33 pixels mm-1 | θmax = 25.0°, θmin = 4.2° |
φ and ω scans | h = −9→9 |
Absorption correction: multi-scan (SADABS; Sheldrick, 1996) | k = −14→14 |
Tmin = 0.654, Tmax = 0.917 | l = 0→14 |
6468 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)] = 0.044 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.131 | H atoms treated by a mixture of independent and constrained refinement |
S = 1.08 | w = 1/[σ2(Fo2) + (0.0832P)2 + 0.0059P] where P = (Fo2 + 2Fc2)/3 |
3973 reflections | (Δ/σ)max = 0.004 |
311 parameters | Δρmax = 0.53 e Å−3 |
91 restraints | Δρmin = −0.33 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 | Occ. (<1) |
Ni1 | 0.73545 (4) | 0.76704 (3) | 0.77014 (3) | 0.04957 (17) | |
Cl1 | 1.06157 (10) | 0.73602 (8) | 0.96401 (7) | 0.0671 (2) | |
O11 | 0.9125 (4) | 0.8281 (3) | 0.9411 (4) | 0.1498 (15) | |
O12 | 1.0126 (5) | 0.6316 (3) | 0.9936 (3) | 0.1285 (13) | |
O13 | 1.1696 (4) | 0.7307 (4) | 0.8681 (2) | 0.1192 (12) | |
O14 | 1.1534 (3) | 0.7426 (3) | 1.0499 (2) | 0.0895 (8) | |
Cl2 | 0.42569 (10) | 0.79180 (7) | 0.56356 (7) | 0.0660 (2) | |
O21 | 0.3354 (4) | 0.7666 (3) | 0.4879 (3) | 0.1099 (10) | |
O22 | 0.5907 (8) | 0.7121 (8) | 0.5738 (9) | 0.171 (3) | 0.63 |
O23 | 0.4397 (15) | 0.9031 (6) | 0.5374 (8) | 0.138 (3) | 0.63 |
O24 | 0.3341 (10) | 0.7742 (9) | 0.6645 (4) | 0.132 (2) | 0.63 |
O22A | 0.5521 (18) | 0.8220 (18) | 0.4884 (11) | 0.185 (6) | 0.37 |
O23A | 0.310 (2) | 0.8968 (12) | 0.5929 (13) | 0.162 (6) | 0.37 |
O24A | 0.4947 (18) | 0.7173 (10) | 0.6535 (9) | 0.140 (4) | 0.37 |
N1 | 1.0091 (3) | 0.5426 (2) | 0.6806 (2) | 0.0701 (7) | |
N2 | 0.9361 (3) | 0.7521 (2) | 0.6698 (2) | 0.0619 (7) | |
H2 | 1.0276 | 0.7420 | 0.7100 | 0.074* | |
N3 | 0.6763 (3) | 0.9324 (2) | 0.7145 (2) | 0.0633 (7) | |
H3 | 0.5986 | 0.9493 | 0.6621 | 0.076* | |
N4 | 0.4487 (4) | 0.9915 (2) | 0.8550 (3) | 0.0731 (8) | |
N5 | 0.5372 (3) | 0.7809 (2) | 0.8727 (2) | 0.0547 (6) | |
H5 | 0.4462 | 0.7852 | 0.8346 | 0.066* | |
N6 | 0.7953 (3) | 0.60199 (18) | 0.8259 (2) | 0.0521 (6) | |
H6 | 0.8812 | 0.5843 | 0.8729 | 0.062* | |
C1 | 1.4878 (5) | 0.3860 (4) | 0.7160 (4) | 0.1114 (15) | |
H1A | 1.4989 | 0.4295 | 0.7679 | 0.167* | |
H1B | 1.5846 | 0.3792 | 0.6638 | 0.167* | |
H1C | 1.4847 | 0.3104 | 0.7540 | 0.167* | |
C2 | 1.3231 (5) | 0.4476 (4) | 0.6567 (4) | 0.0921 (12) | |
H2A | 1.3401 | 0.5121 | 0.6013 | 0.111* | |
H2B | 1.2960 | 0.3948 | 0.6198 | 0.111* | |
C3 | 1.1742 (4) | 0.4914 (3) | 0.7337 (3) | 0.0745 (9) | |
H3A | 1.1647 | 0.4278 | 0.7929 | 0.089* | |
H3B | 1.1978 | 0.5490 | 0.7658 | 0.089* | |
C4 | 0.9831 (5) | 0.6528 (3) | 0.6100 (3) | 0.0752 (9) | |
H4A | 0.8918 | 0.6645 | 0.5616 | 0.090* | |
H4B | 1.0877 | 0.6534 | 0.5647 | 0.090* | |
C5 | 0.9116 (5) | 0.8652 (3) | 0.5921 (3) | 0.0816 (11) | |
H5A | 0.8351 | 0.8721 | 0.5355 | 0.098* | |
H5B | 1.0214 | 0.8721 | 0.5574 | 0.098* | |
C6 | 0.8345 (4) | 0.9565 (3) | 0.6583 (3) | 0.0796 (11) | |
H6A | 0.9143 | 0.9532 | 0.7114 | 0.096* | |
H6B | 0.8065 | 1.0326 | 0.6112 | 0.096* | |
C7 | 0.5976 (5) | 1.0112 (3) | 0.7945 (3) | 0.0752 (9) | |
H7A | 0.6838 | 1.0022 | 0.8456 | 0.090* | |
H7B | 0.5679 | 1.0906 | 0.7543 | 0.090* | |
C8 | 0.2877 (5) | 1.0263 (3) | 0.7977 (4) | 0.0833 (11) | |
H8A | 0.3083 | 0.9880 | 0.7358 | 0.100* | |
H8B | 0.2019 | 0.9991 | 0.8471 | 0.100* | |
C9 | 0.2177 (5) | 1.1493 (4) | 0.7583 (4) | 0.1013 (13) | |
H9A | 0.2963 | 1.1750 | 0.7014 | 0.122* | |
H9B | 0.2107 | 1.1888 | 0.8181 | 0.122* | |
C10 | 0.0399 (5) | 1.1839 (4) | 0.7126 (4) | 0.0957 (13) | |
H10A | 0.0444 | 1.1425 | 0.6555 | 0.144* | |
H10B | 0.0045 | 1.2656 | 0.6831 | 0.144* | |
H10C | −0.0413 | 1.1656 | 0.7702 | 0.144* | |
C11 | 0.4823 (4) | 0.8820 (3) | 0.9287 (3) | 0.0681 (8) | |
H11A | 0.3788 | 0.8791 | 0.9745 | 0.082* | |
H11B | 0.5720 | 0.8754 | 0.9764 | 0.082* | |
C12 | 0.5700 (4) | 0.6713 (3) | 0.9549 (3) | 0.0641 (8) | |
H12A | 0.4633 | 0.6637 | 0.9942 | 0.077* | |
H12B | 0.6502 | 0.6690 | 1.0074 | 0.077* | |
C13 | 0.6452 (4) | 0.5765 (3) | 0.8918 (3) | 0.0658 (8) | |
H13A | 0.6807 | 0.5022 | 0.9415 | 0.079* | |
H13B | 0.5607 | 0.5743 | 0.8444 | 0.079* | |
C14 | 0.8605 (4) | 0.5264 (3) | 0.7426 (3) | 0.0662 (8) | |
H14A | 0.8857 | 0.4462 | 0.7802 | 0.079* | |
H14B | 0.7696 | 0.5413 | 0.6930 | 0.079* | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
Ni1 | 0.0453 (2) | 0.0446 (2) | 0.0553 (3) | −0.01629 (16) | −0.00589 (16) | 0.00353 (16) |
Cl1 | 0.0499 (4) | 0.0831 (6) | 0.0648 (5) | −0.0217 (4) | −0.0100 (4) | −0.0009 (4) |
O11 | 0.091 (2) | 0.130 (3) | 0.192 (4) | 0.022 (2) | −0.049 (2) | −0.016 (3) |
O12 | 0.140 (3) | 0.134 (3) | 0.130 (3) | −0.089 (2) | −0.061 (2) | 0.032 (2) |
O13 | 0.094 (2) | 0.208 (4) | 0.0736 (19) | −0.070 (2) | 0.0026 (15) | −0.030 (2) |
O14 | 0.0677 (15) | 0.128 (2) | 0.0809 (17) | −0.0321 (15) | −0.0068 (12) | −0.0316 (15) |
Cl2 | 0.0619 (5) | 0.0755 (5) | 0.0601 (5) | −0.0211 (4) | −0.0132 (4) | −0.0063 (4) |
O21 | 0.111 (2) | 0.110 (2) | 0.118 (2) | −0.0220 (18) | −0.0399 (19) | −0.0399 (18) |
O22 | 0.076 (4) | 0.184 (8) | 0.213 (9) | 0.028 (4) | −0.041 (5) | −0.034 (7) |
O23 | 0.195 (8) | 0.093 (4) | 0.148 (7) | −0.083 (5) | −0.078 (6) | 0.023 (4) |
O24 | 0.127 (5) | 0.231 (8) | 0.068 (3) | −0.101 (5) | 0.016 (3) | −0.037 (4) |
O22A | 0.135 (10) | 0.205 (15) | 0.225 (17) | −0.105 (11) | 0.060 (11) | −0.018 (14) |
O23A | 0.184 (13) | 0.142 (11) | 0.163 (13) | 0.007 (9) | −0.041 (10) | −0.096 (11) |
O24A | 0.123 (9) | 0.159 (10) | 0.101 (8) | −0.023 (8) | −0.047 (7) | 0.042 (7) |
N1 | 0.0670 (17) | 0.0691 (17) | 0.0652 (17) | −0.0126 (13) | 0.0009 (13) | −0.0079 (13) |
N2 | 0.0560 (14) | 0.0616 (15) | 0.0581 (16) | −0.0189 (12) | −0.0036 (11) | 0.0113 (12) |
N3 | 0.0577 (15) | 0.0490 (13) | 0.0784 (18) | −0.0179 (11) | −0.0138 (13) | 0.0054 (12) |
N4 | 0.0643 (17) | 0.0586 (16) | 0.099 (2) | −0.0131 (13) | −0.0131 (15) | −0.0231 (14) |
N5 | 0.0441 (13) | 0.0517 (13) | 0.0666 (16) | −0.0143 (10) | −0.0081 (11) | −0.0053 (11) |
N6 | 0.0437 (12) | 0.0476 (12) | 0.0599 (15) | −0.0141 (10) | −0.0039 (10) | 0.0011 (10) |
C1 | 0.073 (2) | 0.124 (4) | 0.145 (4) | −0.014 (2) | 0.004 (3) | −0.070 (3) |
C2 | 0.078 (2) | 0.092 (3) | 0.101 (3) | −0.009 (2) | 0.007 (2) | −0.037 (2) |
C3 | 0.069 (2) | 0.069 (2) | 0.079 (2) | −0.0076 (17) | −0.0002 (17) | −0.0205 (17) |
C4 | 0.070 (2) | 0.089 (2) | 0.058 (2) | −0.0214 (18) | 0.0054 (16) | −0.0053 (17) |
C5 | 0.065 (2) | 0.082 (2) | 0.076 (2) | −0.0234 (18) | 0.0052 (17) | 0.0265 (19) |
C6 | 0.071 (2) | 0.0592 (19) | 0.096 (3) | −0.0263 (17) | −0.0111 (19) | 0.0239 (18) |
C7 | 0.079 (2) | 0.0480 (17) | 0.101 (3) | −0.0218 (16) | −0.018 (2) | −0.0097 (17) |
C8 | 0.070 (2) | 0.067 (2) | 0.112 (3) | −0.0060 (17) | −0.016 (2) | −0.031 (2) |
C9 | 0.100 (3) | 0.079 (3) | 0.123 (4) | −0.007 (2) | −0.031 (3) | −0.031 (2) |
C10 | 0.091 (3) | 0.093 (3) | 0.092 (3) | 0.007 (2) | −0.023 (2) | −0.035 (2) |
C11 | 0.0623 (19) | 0.0644 (19) | 0.080 (2) | −0.0178 (15) | −0.0041 (16) | −0.0204 (16) |
C12 | 0.0488 (16) | 0.0674 (19) | 0.068 (2) | −0.0216 (14) | 0.0061 (14) | 0.0046 (15) |
C13 | 0.0541 (17) | 0.0501 (16) | 0.085 (2) | −0.0196 (14) | 0.0022 (15) | 0.0073 (15) |
C14 | 0.0676 (19) | 0.0578 (17) | 0.071 (2) | −0.0174 (15) | −0.0059 (16) | −0.0086 (15) |
Geometric parameters (Å, º) top
Ni1—N2 | 1.932 (3) | C1—C2 | 1.511 (5) |
Ni1—N6 | 1.934 (2) | C1—H1A | 0.9600 |
Ni1—N5 | 1.934 (2) | C1—H1B | 0.9600 |
Ni1—N3 | 1.937 (2) | C1—H1C | 0.9600 |
Ni1—O24A | 2.863 (11) | C2—C3 | 1.501 (5) |
Ni1—O11 | 3.060 (4) | C2—H2A | 0.9700 |
Ni1—O22 | 3.134 (9) | C2—H2B | 0.9700 |
Cl1—O11 | 1.392 (3) | C3—H3A | 0.9700 |
Cl1—O13 | 1.406 (3) | C3—H3B | 0.9700 |
Cl1—O14 | 1.411 (3) | C4—H4A | 0.9700 |
Cl1—O12 | 1.432 (3) | C4—H4B | 0.9700 |
Cl2—O24A | 1.341 (7) | C5—C6 | 1.490 (6) |
Cl2—O23 | 1.384 (5) | C5—H5A | 0.9700 |
Cl2—O22A | 1.396 (8) | C5—H5B | 0.9700 |
Cl2—O24 | 1.402 (5) | C6—H6A | 0.9700 |
Cl2—O22 | 1.402 (5) | C6—H6B | 0.9700 |
Cl2—O21 | 1.405 (3) | C7—H7A | 0.9700 |
Cl2—O23A | 1.446 (9) | C7—H7B | 0.9700 |
N1—C14 | 1.407 (4) | C8—C9 | 1.444 (5) |
N1—C4 | 1.421 (4) | C8—H8A | 0.9700 |
N1—C3 | 1.466 (4) | C8—H8B | 0.9700 |
N2—C5 | 1.489 (4) | C9—C10 | 1.521 (5) |
N2—C4 | 1.510 (5) | C9—H9A | 0.9700 |
N2—H2 | 0.9100 | C9—H9B | 0.9700 |
N3—C6 | 1.479 (4) | C10—H10A | 0.9600 |
N3—C7 | 1.507 (5) | C10—H10B | 0.9600 |
N3—H3 | 0.9100 | C10—H10C | 0.9600 |
N4—C7 | 1.414 (4) | C11—H11A | 0.9700 |
N4—C11 | 1.428 (4) | C11—H11B | 0.9700 |
N4—C8 | 1.468 (4) | C12—C13 | 1.497 (5) |
N5—C12 | 1.480 (4) | C12—H12A | 0.9700 |
N5—C11 | 1.496 (4) | C12—H12B | 0.9700 |
N5—H5 | 0.9100 | C13—H13A | 0.9700 |
N6—C13 | 1.474 (4) | C13—H13B | 0.9700 |
N6—C14 | 1.499 (4) | C14—H14A | 0.9700 |
N6—H6 | 0.9100 | C14—H14B | 0.9700 |
| | | |
N2—Ni1—N6 | 92.47 (10) | H1A—C1—H1C | 109.5 |
N2—Ni1—N5 | 178.99 (9) | H1B—C1—H1C | 109.5 |
N6—Ni1—N5 | 87.05 (9) | C3—C2—C1 | 111.9 (3) |
N2—Ni1—N3 | 87.44 (11) | C3—C2—H2A | 109.2 |
N6—Ni1—N3 | 179.79 (10) | C1—C2—H2A | 109.2 |
N5—Ni1—N3 | 93.03 (11) | C3—C2—H2B | 109.2 |
N2—Ni1—O24A | 102.8 (3) | C1—C2—H2B | 109.2 |
N6—Ni1—O24A | 82.0 (2) | H2A—C2—H2B | 107.9 |
N5—Ni1—O24A | 78.0 (3) | N1—C3—C2 | 113.4 (3) |
N3—Ni1—O24A | 98.2 (2) | N1—C3—H3A | 108.9 |
N2—Ni1—O11 | 92.56 (12) | C2—C3—H3A | 108.9 |
N6—Ni1—O11 | 97.56 (10) | N1—C3—H3B | 108.9 |
N5—Ni1—O11 | 86.62 (11) | C2—C3—H3B | 108.9 |
N3—Ni1—O11 | 82.26 (11) | H3A—C3—H3B | 107.7 |
O24A—Ni1—O11 | 164.6 (3) | N1—C4—N2 | 113.8 (3) |
N2—Ni1—O22 | 80.5 (2) | N1—C4—H4A | 108.8 |
N6—Ni1—O22 | 84.93 (19) | N2—C4—H4A | 108.8 |
N5—Ni1—O22 | 100.3 (2) | N1—C4—H4B | 108.8 |
N3—Ni1—O22 | 95.2 (2) | N2—C4—H4B | 108.8 |
O11—Ni1—O22 | 172.8 (2) | H4A—C4—H4B | 107.7 |
O11—Cl1—O13 | 108.7 (2) | N2—C5—C6 | 106.5 (3) |
O11—Cl1—O14 | 114.0 (2) | N2—C5—H5A | 110.4 |
O13—Cl1—O14 | 109.46 (17) | C6—C5—H5A | 110.4 |
O11—Cl1—O12 | 107.9 (3) | N2—C5—H5B | 110.4 |
O13—Cl1—O12 | 108.1 (3) | C6—C5—H5B | 110.4 |
O14—Cl1—O12 | 108.52 (18) | H5A—C5—H5B | 108.6 |
O24A—Cl2—O23 | 121.3 (6) | N3—C6—C5 | 106.0 (3) |
O24A—Cl2—O22A | 111.7 (8) | N3—C6—H6A | 110.5 |
O23—Cl2—O22A | 57.7 (6) | C5—C6—H6A | 110.5 |
O24A—Cl2—O24 | 56.0 (6) | N3—C6—H6B | 110.5 |
O23—Cl2—O24 | 110.5 (5) | C5—C6—H6B | 110.5 |
O22A—Cl2—O24 | 158.1 (7) | H6A—C6—H6B | 108.7 |
O24A—Cl2—O22 | 51.6 (5) | N4—C7—N3 | 114.8 (3) |
O23—Cl2—O22 | 109.5 (5) | N4—C7—H7A | 108.6 |
O22A—Cl2—O22 | 65.0 (7) | N3—C7—H7A | 108.6 |
O24—Cl2—O22 | 107.5 (5) | N4—C7—H7B | 108.6 |
O24A—Cl2—O21 | 124.8 (6) | N3—C7—H7B | 108.6 |
O23—Cl2—O21 | 113.9 (3) | H7A—C7—H7B | 107.5 |
O22A—Cl2—O21 | 96.4 (6) | C9—C8—N4 | 115.0 (3) |
O24—Cl2—O21 | 105.4 (3) | C9—C8—H8A | 108.5 |
O22—Cl2—O21 | 109.8 (4) | N4—C8—H8A | 108.5 |
O24A—Cl2—O23A | 110.2 (8) | C9—C8—H8B | 108.5 |
O23—Cl2—O23A | 50.5 (6) | N4—C8—H8B | 108.5 |
O22A—Cl2—O23A | 107.8 (9) | H8A—C8—H8B | 107.5 |
O24—Cl2—O23A | 66.0 (7) | C8—C9—C10 | 113.7 (4) |
O22—Cl2—O23A | 145.8 (6) | C8—C9—H9A | 108.8 |
O21—Cl2—O23A | 104.2 (5) | C10—C9—H9A | 108.8 |
C14—N1—C4 | 114.3 (3) | C8—C9—H9B | 108.8 |
C14—N1—C3 | 117.4 (3) | C10—C9—H9B | 108.8 |
C4—N1—C3 | 117.2 (3) | H9A—C9—H9B | 107.7 |
C5—N2—C4 | 111.6 (3) | C9—C10—H10A | 109.5 |
C5—N2—Ni1 | 107.2 (2) | C9—C10—H10B | 109.5 |
C4—N2—Ni1 | 117.0 (2) | H10A—C10—H10B | 109.5 |
C5—N2—H2 | 106.8 | C9—C10—H10C | 109.5 |
C4—N2—H2 | 106.8 | H10A—C10—H10C | 109.5 |
Ni1—N2—H2 | 106.8 | H10B—C10—H10C | 109.5 |
C6—N3—C7 | 110.9 (3) | N4—C11—N5 | 113.9 (3) |
C6—N3—Ni1 | 106.73 (18) | N4—C11—H11A | 108.8 |
C7—N3—Ni1 | 117.9 (2) | N5—C11—H11A | 108.8 |
C6—N3—H3 | 106.9 | N4—C11—H11B | 108.8 |
C7—N3—H3 | 106.9 | N5—C11—H11B | 108.8 |
Ni1—N3—H3 | 106.9 | H11A—C11—H11B | 107.7 |
C7—N4—C11 | 113.4 (3) | N5—C12—C13 | 106.1 (3) |
C7—N4—C8 | 118.3 (3) | N5—C12—H12A | 110.5 |
C11—N4—C8 | 114.6 (3) | C13—C12—H12A | 110.5 |
C12—N5—C11 | 110.3 (3) | N5—C12—H12B | 110.5 |
C12—N5—Ni1 | 107.26 (17) | C13—C12—H12B | 110.5 |
C11—N5—Ni1 | 118.4 (2) | H12A—C12—H12B | 108.7 |
C12—N5—H5 | 106.8 | N6—C13—C12 | 106.6 (2) |
C11—N5—H5 | 106.8 | N6—C13—H13A | 110.4 |
Ni1—N5—H5 | 106.8 | C12—C13—H13A | 110.4 |
C13—N6—C14 | 111.5 (2) | N6—C13—H13B | 110.4 |
C13—N6—Ni1 | 107.98 (16) | C12—C13—H13B | 110.4 |
C14—N6—Ni1 | 116.32 (18) | H13A—C13—H13B | 108.6 |
C13—N6—H6 | 106.9 | N1—C14—N6 | 114.3 (3) |
C14—N6—H6 | 106.9 | N1—C14—H14A | 108.7 |
Ni1—N6—H6 | 106.9 | N6—C14—H14A | 108.7 |
C2—C1—H1A | 109.5 | N1—C14—H14B | 108.7 |
C2—C1—H1B | 109.5 | N6—C14—H14B | 108.7 |
H1A—C1—H1B | 109.5 | H14A—C14—H14B | 107.6 |
C2—C1—H1C | 109.5 | | |
Hydrogen-bond geometry (Å, º) top
D—H···A | D—H | H···A | D···A | D—H···A |
N2—H2···O13 | 0.91 | 2.36 | 3.217 (4) | 156 |
N2—H2···O24i | 0.91 | 2.63 | 3.336 (6) | 135 |
N3—H3···O23 | 0.91 | 2.40 | 3.250 (7) | 155 |
N5—H5···O24 | 0.91 | 2.46 | 3.276 (6) | 150 |
N5—H5···O13ii | 0.91 | 2.52 | 3.258 (4) | 139 |
N6—H6···O12 | 0.91 | 2.22 | 3.050 (4) | 151 |
Symmetry codes: (i) x+1, y, z; (ii) x−1, y, z. |