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metal-organic compounds
The double chelate ring in the title complex, [Ni(C15H11ClN3O3)2]·C5H5N, is essentially planar, with the O,N,O-donor atoms and a pyridine ligand N atom occuping the equatorial positions in a distorted octahedral environment about the Ni atom. The N-Ni-N axial bond angle is 173.16 (8)°.
Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536804013030/su6095sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S1600536804013030/su6095Isup2.hkl |
CCDC reference: 245112
Key indicators
- Single-crystal X-ray study
- T = 273 K
- Mean (C-C) = 0.005 Å
- R factor = 0.057
- wR factor = 0.139
- Data-to-parameter ratio = 17.8
checkCIF/PLATON results
No syntax errors found
Alert level C PLAT094_ALERT_2_C Ratio of Maximum / Minimum Residual Density .... 3.17 PLAT125_ALERT_4_C No _symmetry_space_group_name_Hall Given ....... ? PLAT220_ALERT_2_C Large Non-Solvent C Ueq(max)/Ueq(min) ... 2.79 Ratio PLAT220_ALERT_2_C Large Non-Solvent O Ueq(max)/Ueq(min) ... 2.77 Ratio PLAT241_ALERT_2_C Check High U(eq) as Compared to Neighbors .... C19 PLAT241_ALERT_2_C Check High U(eq) as Compared to Neighbors .... C24 PLAT242_ALERT_2_C Check Low U(eq) as Compared to Neighbors .... N3 PLAT242_ALERT_2_C Check Low U(eq) as Compared to Neighbors .... N4 PLAT242_ALERT_2_C Check Low U(eq) as Compared to Neighbors .... N5 PLAT243_ALERT_4_C High Solvent U(eq) as Compared to Neighbors .... N7 PLAT244_ALERT_4_C Low Solvent U(eq) as Compared to Neighbors .... C32 PLAT244_ALERT_4_C Low Solvent U(eq) as Compared to Neighbors .... C35 PLAT380_ALERT_4_C Incorrectly Oriented X(sp2)-Methyl Moiety ...... C8 PLAT710_ALERT_4_C Delete 1-2-3 or 2-3-4 Linear Torsion Angle ... # 2 O2 -NI1 -O1 -C1 -15.90 0.60 1.555 1.555 1.555 1.555 PLAT710_ALERT_4_C Delete 1-2-3 or 2-3-4 Linear Torsion Angle ... # 6 O1 -NI1 -O2 -C9 4.40 0.50 1.555 1.555 1.555 1.555 PLAT710_ALERT_4_C Delete 1-2-3 or 2-3-4 Linear Torsion Angle ... # 13 N6 -NI1 -N1 -C7 -171.70 1.00 1.555 1.555 1.555 1.555 PLAT710_ALERT_4_C Delete 1-2-3 or 2-3-4 Linear Torsion Angle ... # 18 N6 -NI1 -N1 -N2 9.30 1.20 1.555 1.555 1.555 1.555 PLAT710_ALERT_4_C Delete 1-2-3 or 2-3-4 Linear Torsion Angle ... # 27 N5 -NI1 -N4 -C16 128.00 0.70 1.555 1.555 1.555 1.555 PLAT710_ALERT_4_C Delete 1-2-3 or 2-3-4 Linear Torsion Angle ... # 32 N5 -NI1 -N4 -C20 -51.80 0.80 1.555 1.555 1.555 1.555 PLAT710_ALERT_4_C Delete 1-2-3 or 2-3-4 Linear Torsion Angle ... # 37 N4 -NI1 -N5 -C21 44.70 0.80 1.555 1.555 1.555 1.555 PLAT710_ALERT_4_C Delete 1-2-3 or 2-3-4 Linear Torsion Angle ... # 42 N4 -NI1 -N5 -C25 -128.80 0.70 1.555 1.555 1.555 1.555 PLAT710_ALERT_4_C Delete 1-2-3 or 2-3-4 Linear Torsion Angle ... # 44 N1 -NI1 -N6 -C30 -12.10 1.20 1.555 1.555 1.555 1.555 PLAT710_ALERT_4_C Delete 1-2-3 or 2-3-4 Linear Torsion Angle ... # 49 N1 -NI1 -N6 -C26 165.20 1.00 1.555 1.555 1.555 1.555
0 ALERT level A = In general: serious problem 0 ALERT level B = Potentially serious problem 23 ALERT level C = Check and explain 0 ALERT level G = General alerts; check 0 ALERT type 1 CIF construction/syntax error, inconsistent or missing data 8 ALERT type 2 Indicator that the structure model may be wrong or deficient 0 ALERT type 3 Indicator that the structure quality may be low 15 ALERT type 4 Improvement, methodology, query or suggestion
Computing details top
Data collection: SMART (Siemens, 1996); cell refinement: SAINT (Siemens, 1996); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997a); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997a); molecular graphics: SHELXTL (Sheldrick, 1997b); software used to prepare material for publication: SHELXTL, PARST (Nardelli, 1995) and PLATON (Spek, 2003).
[1-(5-Chloro-2-oxidophenyl)ethanone
4-nitrobenzoylhydrazonato(2-)]tripyridinenickel(II) pyridine solvate top
Crystal data top
[Ni(C15H11ClN3O3)2]·C5H5N | F(000) = 1464 |
Mr = 706.82 | Dx = 1.387 Mg m−3 |
Monoclinic, P21/n | Mo Kα radiation, λ = 0.71073 Å |
a = 12.585 (2) Å | Cell parameters from 4938 reflections |
b = 21.175 (3) Å | θ = 1.8–27.5° |
c = 12.704 (2) Å | µ = 0.70 mm−1 |
β = 90.211 (3)° | T = 273 K |
V = 3385.7 (9) Å3 | Block, dark orange |
Z = 4 | 0.42 × 0.23 × 0.14 mm |
Data collection top
Bruker SMART APEX area-detector diffractometer | 7728 independent reflections |
Radiation source: fine-focus sealed tube | 5161 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.036 |
Detector resolution: 83.66 pixels mm-1 | θmax = 27.5°, θmin = 1.8° |
ω scans | h = −16→13 |
Absorption correction: multi-scan (SADABS; Sheldrick, 1996) | k = −27→27 |
Tmin = 0.757, Tmax = 0.908 | l = −16→16 |
26253 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)] = 0.057 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.139 | H-atom parameters constrained |
S = 1.06 | w = 1/[σ2(Fo2) + (0.0629P)2 + 0.3467P] where P = (Fo2 + 2Fc2)/3 |
7728 reflections | (Δ/σ)max < 0.001 |
433 parameters | Δρmax = 0.57 e Å−3 |
0 restraints | Δρmin = −0.18 e Å−3 |
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
x | y | z | Uiso*/Ueq | ||
Ni1 | 0.17899 (3) | 0.250461 (14) | 0.30205 (2) | 0.04754 (12) | |
O1 | 0.15109 (15) | 0.34085 (8) | 0.27369 (14) | 0.0565 (5) | |
O2 | 0.21929 (14) | 0.16262 (8) | 0.35365 (13) | 0.0510 (4) | |
O3 | 0.4132 (2) | −0.10769 (12) | 0.5795 (2) | 0.1140 (10) | |
O4 | 0.4154 (3) | −0.06359 (13) | 0.7287 (2) | 0.1410 (13) | |
N1 | 0.23282 (16) | 0.27196 (10) | 0.44701 (16) | 0.0457 (5) | |
N2 | 0.27185 (17) | 0.21956 (10) | 0.50180 (17) | 0.0480 (5) | |
N4 | 0.33748 (19) | 0.25760 (10) | 0.23517 (18) | 0.0544 (6) | |
N5 | 0.01678 (18) | 0.23477 (11) | 0.35474 (18) | 0.0557 (6) | |
N6 | 0.12419 (17) | 0.22084 (11) | 0.15410 (17) | 0.0537 (6) | |
N7 | 0.1001 (4) | 0.9853 (2) | 0.2618 (8) | 0.179 (3) | |
C1 | 0.1557 (2) | 0.38711 (12) | 0.3405 (2) | 0.0507 (6) | |
C2 | 0.1184 (2) | 0.44636 (13) | 0.3058 (2) | 0.0636 (8) | |
H2B | 0.0935 | 0.4497 | 0.2370 | 0.076* | |
C3 | 0.1167 (3) | 0.49945 (13) | 0.3677 (3) | 0.0690 (8) | |
H3A | 0.0912 | 0.5376 | 0.3416 | 0.083* | |
C4 | 0.1535 (2) | 0.49475 (12) | 0.4693 (3) | 0.0637 (8) | |
C5 | 0.1916 (2) | 0.43909 (12) | 0.5071 (2) | 0.0575 (7) | |
H5A | 0.2165 | 0.4376 | 0.5761 | 0.069* | |
C6 | 0.1950 (2) | 0.38340 (11) | 0.4460 (2) | 0.0480 (6) | |
C7 | 0.2380 (2) | 0.32591 (12) | 0.4959 (2) | 0.0488 (6) | |
C8 | 0.2880 (2) | 0.33065 (13) | 0.6035 (2) | 0.0655 (8) | |
H8A | 0.3122 | 0.2897 | 0.6254 | 0.098* | |
H8B | 0.2365 | 0.3461 | 0.6528 | 0.098* | |
H8C | 0.3472 | 0.3592 | 0.6010 | 0.098* | |
C9 | 0.26072 (19) | 0.16772 (12) | 0.4457 (2) | 0.0456 (6) | |
C10 | 0.30087 (19) | 0.10850 (12) | 0.4967 (2) | 0.0468 (6) | |
C11 | 0.3051 (2) | 0.05383 (13) | 0.4385 (2) | 0.0606 (7) | |
H11A | 0.2845 | 0.0545 | 0.3681 | 0.073* | |
C12 | 0.3396 (2) | −0.00236 (13) | 0.4832 (2) | 0.0648 (8) | |
H12A | 0.3427 | −0.0392 | 0.4436 | 0.078* | |
C13 | 0.3688 (2) | −0.00225 (13) | 0.5863 (2) | 0.0579 (7) | |
C14 | 0.3664 (3) | 0.05127 (14) | 0.6462 (2) | 0.0708 (9) | |
H14A | 0.3870 | 0.0501 | 0.7166 | 0.085* | |
C15 | 0.3329 (2) | 0.10717 (13) | 0.6007 (2) | 0.0640 (8) | |
H15A | 0.3319 | 0.1441 | 0.6404 | 0.077* | |
N3 | 0.4020 (2) | −0.06191 (12) | 0.6351 (3) | 0.0755 (8) | |
C16 | 0.3779 (3) | 0.31204 (15) | 0.2068 (3) | 0.0742 (9) | |
H16A | 0.3368 | 0.3480 | 0.2165 | 0.089* | |
C17 | 0.4763 (3) | 0.31925 (18) | 0.1640 (3) | 0.0902 (11) | |
H17A | 0.5010 | 0.3592 | 0.1460 | 0.108* | |
C18 | 0.5376 (3) | 0.2678 (2) | 0.1480 (3) | 0.0877 (11) | |
H18A | 0.6047 | 0.2714 | 0.1182 | 0.105* | |
C19 | 0.4985 (3) | 0.2109 (2) | 0.1765 (3) | 0.1079 (15) | |
H19A | 0.5386 | 0.1745 | 0.1667 | 0.129* | |
C20 | 0.3996 (3) | 0.20749 (16) | 0.2200 (3) | 0.0895 (12) | |
H20A | 0.3742 | 0.1681 | 0.2400 | 0.107* | |
C21 | −0.0210 (3) | 0.17734 (16) | 0.3653 (3) | 0.0800 (10) | |
H21A | 0.0254 | 0.1436 | 0.3558 | 0.096* | |
C22 | −0.1253 (3) | 0.16412 (18) | 0.3896 (3) | 0.0986 (13) | |
H22A | −0.1483 | 0.1225 | 0.3956 | 0.118* | |
C23 | −0.1935 (3) | 0.2122 (2) | 0.4045 (3) | 0.1008 (13) | |
H23A | −0.2640 | 0.2048 | 0.4223 | 0.121* | |
C24 | −0.1566 (3) | 0.2709 (2) | 0.3927 (5) | 0.127 (2) | |
H24A | −0.2022 | 0.3051 | 0.4011 | 0.153* | |
C25 | −0.0518 (3) | 0.28100 (17) | 0.3684 (3) | 0.0968 (13) | |
H25A | −0.0282 | 0.3224 | 0.3612 | 0.116* | |
C26 | 0.0747 (2) | 0.26021 (14) | 0.0891 (2) | 0.0616 (8) | |
H26A | 0.0670 | 0.3021 | 0.1096 | 0.074* | |
C27 | 0.0345 (3) | 0.24224 (17) | −0.0063 (3) | 0.0734 (9) | |
H27A | 0.0010 | 0.2715 | −0.0499 | 0.088* | |
C28 | 0.0443 (3) | 0.1810 (2) | −0.0366 (3) | 0.0822 (10) | |
H28A | 0.0166 | 0.1674 | −0.1006 | 0.099* | |
C29 | 0.0958 (3) | 0.13981 (18) | 0.0288 (3) | 0.0883 (11) | |
H29A | 0.1048 | 0.0978 | 0.0095 | 0.106* | |
C30 | 0.1336 (3) | 0.16143 (15) | 0.1231 (2) | 0.0745 (9) | |
H30A | 0.1677 | 0.1330 | 0.1677 | 0.089* | |
C31 | 0.0339 (6) | 0.9924 (3) | 0.3485 (5) | 0.137 (2) | |
H31A | 0.0623 | 0.9937 | 0.4162 | 0.164* | |
C32 | −0.0655 (5) | 0.9972 (2) | 0.3340 (5) | 0.1157 (16) | |
H32A | −0.1103 | 1.0011 | 0.3917 | 0.139* | |
C33 | −0.1059 (4) | 0.9968 (3) | 0.2391 (6) | 0.1307 (19) | |
H33A | −0.1789 | 1.0018 | 0.2310 | 0.157* | |
C34 | −0.0483 (6) | 0.9896 (3) | 0.1562 (5) | 0.1275 (18) | |
H34A | −0.0800 | 0.9889 | 0.0899 | 0.153* | |
C35 | 0.0520 (7) | 0.9835 (2) | 0.1649 (6) | 0.135 (2) | |
H35A | 0.0930 | 0.9777 | 0.1050 | 0.161* | |
Cl1 | 0.15041 (8) | 0.56194 (4) | 0.54950 (8) | 0.0922 (3) |
Atomic displacement parameters (Å2) top
U11 | U22 | U33 | U12 | U13 | U23 | |
Ni1 | 0.0530 (2) | 0.0468 (2) | 0.0429 (2) | 0.00384 (14) | 0.00186 (15) | −0.00260 (14) |
O1 | 0.0689 (13) | 0.0498 (10) | 0.0508 (11) | 0.0069 (9) | 0.0006 (9) | −0.0003 (9) |
O2 | 0.0604 (12) | 0.0488 (10) | 0.0438 (10) | 0.0018 (8) | −0.0028 (9) | −0.0021 (8) |
O3 | 0.163 (3) | 0.0594 (15) | 0.119 (2) | 0.0278 (16) | −0.0157 (19) | 0.0048 (15) |
O4 | 0.245 (4) | 0.0817 (19) | 0.096 (2) | 0.024 (2) | −0.059 (2) | 0.0179 (16) |
N1 | 0.0459 (13) | 0.0461 (11) | 0.0452 (12) | 0.0002 (9) | 0.0062 (10) | −0.0006 (10) |
N2 | 0.0522 (13) | 0.0458 (12) | 0.0461 (12) | 0.0015 (10) | 0.0028 (10) | −0.0013 (10) |
N4 | 0.0569 (15) | 0.0597 (15) | 0.0466 (12) | 0.0030 (11) | 0.0045 (10) | 0.0001 (11) |
N5 | 0.0532 (14) | 0.0596 (14) | 0.0544 (14) | 0.0002 (11) | 0.0049 (11) | −0.0094 (11) |
N6 | 0.0573 (15) | 0.0600 (14) | 0.0438 (12) | 0.0055 (11) | 0.0002 (11) | −0.0057 (11) |
N7 | 0.110 (4) | 0.116 (4) | 0.312 (9) | −0.011 (3) | −0.014 (5) | −0.042 (5) |
C1 | 0.0484 (16) | 0.0462 (14) | 0.0576 (16) | −0.0010 (11) | 0.0131 (13) | 0.0015 (13) |
C2 | 0.069 (2) | 0.0569 (17) | 0.0655 (19) | 0.0052 (14) | 0.0090 (15) | 0.0069 (15) |
C3 | 0.076 (2) | 0.0473 (16) | 0.084 (2) | 0.0057 (14) | 0.0127 (18) | 0.0056 (16) |
C4 | 0.068 (2) | 0.0441 (15) | 0.079 (2) | −0.0016 (13) | 0.0179 (17) | −0.0103 (14) |
C5 | 0.0602 (18) | 0.0500 (15) | 0.0623 (18) | −0.0047 (13) | 0.0089 (14) | −0.0071 (13) |
C6 | 0.0449 (15) | 0.0466 (14) | 0.0527 (16) | −0.0012 (11) | 0.0105 (12) | −0.0028 (12) |
C7 | 0.0456 (15) | 0.0520 (15) | 0.0490 (15) | −0.0040 (11) | 0.0068 (12) | −0.0057 (12) |
C8 | 0.074 (2) | 0.0595 (17) | 0.0632 (19) | 0.0016 (14) | −0.0089 (15) | −0.0117 (14) |
C9 | 0.0427 (15) | 0.0500 (14) | 0.0440 (14) | −0.0003 (11) | 0.0059 (11) | 0.0011 (12) |
C10 | 0.0428 (15) | 0.0503 (14) | 0.0474 (15) | 0.0009 (11) | 0.0007 (11) | −0.0001 (12) |
C11 | 0.077 (2) | 0.0557 (16) | 0.0488 (16) | 0.0053 (14) | −0.0047 (14) | −0.0048 (13) |
C12 | 0.084 (2) | 0.0482 (16) | 0.0624 (19) | 0.0069 (14) | −0.0016 (16) | −0.0054 (13) |
C13 | 0.0566 (18) | 0.0518 (16) | 0.0653 (19) | 0.0009 (12) | −0.0048 (14) | 0.0080 (14) |
C14 | 0.091 (2) | 0.0646 (19) | 0.0566 (18) | 0.0049 (16) | −0.0186 (16) | 0.0026 (15) |
C15 | 0.084 (2) | 0.0524 (16) | 0.0558 (17) | 0.0051 (15) | −0.0105 (15) | −0.0057 (13) |
N3 | 0.085 (2) | 0.0551 (16) | 0.086 (2) | 0.0055 (14) | −0.0155 (16) | 0.0097 (15) |
C16 | 0.076 (2) | 0.063 (2) | 0.084 (2) | 0.0037 (16) | 0.0246 (18) | −0.0033 (17) |
C17 | 0.085 (3) | 0.082 (2) | 0.103 (3) | −0.013 (2) | 0.030 (2) | −0.001 (2) |
C18 | 0.074 (2) | 0.109 (3) | 0.079 (2) | 0.008 (2) | 0.032 (2) | 0.010 (2) |
C19 | 0.091 (3) | 0.098 (3) | 0.135 (4) | 0.034 (2) | 0.060 (3) | 0.025 (3) |
C20 | 0.088 (3) | 0.072 (2) | 0.108 (3) | 0.0148 (19) | 0.041 (2) | 0.018 (2) |
C21 | 0.067 (2) | 0.069 (2) | 0.103 (3) | 0.0009 (17) | 0.0105 (19) | 0.0002 (19) |
C22 | 0.073 (3) | 0.082 (3) | 0.141 (4) | −0.018 (2) | 0.022 (2) | −0.012 (2) |
C23 | 0.063 (2) | 0.103 (3) | 0.137 (4) | −0.014 (2) | 0.033 (2) | −0.038 (3) |
C24 | 0.069 (3) | 0.084 (3) | 0.229 (6) | 0.001 (2) | 0.049 (3) | −0.047 (3) |
C25 | 0.070 (2) | 0.068 (2) | 0.153 (4) | −0.0036 (18) | 0.032 (2) | −0.029 (2) |
C26 | 0.0594 (19) | 0.0655 (19) | 0.0600 (18) | 0.0056 (14) | −0.0008 (15) | 0.0026 (14) |
C27 | 0.062 (2) | 0.097 (3) | 0.0607 (19) | −0.0056 (17) | −0.0132 (16) | 0.0111 (18) |
C28 | 0.084 (3) | 0.109 (3) | 0.0532 (19) | −0.018 (2) | −0.0094 (17) | −0.014 (2) |
C29 | 0.114 (3) | 0.080 (2) | 0.071 (2) | 0.001 (2) | −0.011 (2) | −0.0242 (19) |
C30 | 0.098 (3) | 0.067 (2) | 0.0580 (19) | 0.0113 (17) | −0.0133 (17) | −0.0064 (15) |
C31 | 0.134 (5) | 0.151 (5) | 0.125 (5) | 0.022 (4) | −0.042 (4) | −0.045 (4) |
C32 | 0.115 (4) | 0.116 (4) | 0.116 (4) | 0.033 (3) | 0.035 (3) | 0.003 (3) |
C33 | 0.073 (3) | 0.145 (5) | 0.174 (6) | 0.006 (3) | −0.010 (4) | 0.021 (4) |
C34 | 0.132 (5) | 0.151 (5) | 0.099 (4) | −0.005 (4) | −0.009 (4) | −0.015 (3) |
C35 | 0.142 (6) | 0.099 (3) | 0.163 (6) | −0.014 (4) | 0.079 (5) | −0.026 (4) |
Cl1 | 0.1156 (8) | 0.0507 (4) | 0.1103 (7) | 0.0009 (4) | 0.0134 (6) | −0.0229 (4) |
Geometric parameters (Å, º) top
Ni1—O1 | 1.9787 (18) | C12—H12A | 0.9300 |
Ni1—N1 | 2.012 (2) | C13—C14 | 1.366 (4) |
Ni1—O2 | 2.0357 (17) | C13—N3 | 1.468 (4) |
Ni1—N6 | 2.096 (2) | C14—C15 | 1.383 (4) |
Ni1—N4 | 2.176 (2) | C14—H14A | 0.9300 |
Ni1—N5 | 2.176 (2) | C15—H15A | 0.9300 |
O1—C1 | 1.297 (3) | C16—C17 | 1.363 (4) |
O2—C9 | 1.283 (3) | C16—H16A | 0.9300 |
O3—N3 | 1.208 (3) | C17—C18 | 1.351 (5) |
O4—N3 | 1.200 (4) | C17—H17A | 0.9300 |
N1—C7 | 1.302 (3) | C18—C19 | 1.351 (5) |
N1—N2 | 1.398 (3) | C18—H18A | 0.9300 |
N2—C9 | 1.316 (3) | C19—C20 | 1.366 (5) |
N4—C16 | 1.311 (4) | C19—H19A | 0.9300 |
N4—C20 | 1.333 (4) | C20—H20A | 0.9300 |
N5—C21 | 1.313 (4) | C21—C22 | 1.379 (4) |
N5—C25 | 1.317 (4) | C21—H21A | 0.9300 |
N6—C30 | 1.323 (4) | C22—C23 | 1.345 (5) |
N6—C26 | 1.327 (4) | C22—H22A | 0.9300 |
N7—C35 | 1.370 (8) | C23—C24 | 1.336 (6) |
N7—C31 | 1.391 (8) | C23—H23A | 0.9300 |
C1—C2 | 1.410 (4) | C24—C25 | 1.372 (5) |
C1—C6 | 1.429 (4) | C24—H24A | 0.9300 |
C2—C3 | 1.372 (4) | C25—H25A | 0.9300 |
C2—H2B | 0.9300 | C26—C27 | 1.366 (4) |
C3—C4 | 1.374 (4) | C26—H26A | 0.9300 |
C3—H3A | 0.9300 | C27—C28 | 1.358 (5) |
C4—C5 | 1.359 (4) | C27—H27A | 0.9300 |
C4—Cl1 | 1.751 (3) | C28—C29 | 1.366 (5) |
C5—C6 | 1.412 (3) | C28—H28A | 0.9300 |
C5—H5A | 0.9300 | C29—C30 | 1.367 (4) |
C6—C7 | 1.474 (4) | C29—H29A | 0.9300 |
C7—C8 | 1.507 (4) | C30—H30A | 0.9300 |
C8—H8A | 0.9600 | C31—C32 | 1.268 (7) |
C8—H8B | 0.9600 | C31—H31A | 0.9300 |
C8—H8C | 0.9600 | C32—C33 | 1.307 (7) |
C9—C10 | 1.498 (3) | C32—H32A | 0.9300 |
C10—C11 | 1.375 (3) | C33—C34 | 1.290 (7) |
C10—C15 | 1.380 (4) | C33—H33A | 0.9300 |
C11—C12 | 1.388 (4) | C34—C35 | 1.273 (7) |
C11—H11A | 0.9300 | C34—H34A | 0.9300 |
C12—C13 | 1.358 (4) | C35—H35A | 0.9300 |
O1—Ni1—N1 | 90.39 (8) | C12—C13—N3 | 118.8 (3) |
O1—Ni1—O2 | 170.49 (7) | C14—C13—N3 | 119.0 (3) |
N1—Ni1—O2 | 80.17 (8) | C13—C14—C15 | 119.0 (3) |
O1—Ni1—N6 | 93.93 (8) | C13—C14—H14A | 120.5 |
N1—Ni1—N6 | 175.66 (8) | C15—C14—H14A | 120.5 |
O2—Ni1—N6 | 95.52 (8) | C10—C15—C14 | 120.4 (3) |
O1—Ni1—N4 | 91.37 (8) | C10—C15—H15A | 119.8 |
N1—Ni1—N4 | 92.04 (9) | C14—C15—H15A | 119.8 |
O2—Ni1—N4 | 87.80 (8) | O4—N3—O3 | 122.7 (3) |
N6—Ni1—N4 | 88.26 (9) | O4—N3—C13 | 118.9 (3) |
O1—Ni1—N5 | 92.16 (8) | O3—N3—C13 | 118.4 (3) |
N1—Ni1—N5 | 93.79 (8) | N4—C16—C17 | 124.2 (3) |
O2—Ni1—N5 | 89.68 (8) | N4—C16—H16A | 117.9 |
N6—Ni1—N5 | 85.65 (9) | C17—C16—H16A | 117.9 |
N4—Ni1—N5 | 173.16 (8) | C18—C17—C16 | 119.4 (3) |
C1—O1—Ni1 | 127.13 (17) | C18—C17—H17A | 120.3 |
C9—O2—Ni1 | 108.45 (15) | C16—C17—H17A | 120.3 |
C7—N1—N2 | 116.2 (2) | C17—C18—C19 | 118.0 (3) |
C7—N1—Ni1 | 130.63 (19) | C17—C18—H18A | 121.0 |
N2—N1—Ni1 | 113.13 (15) | C19—C18—H18A | 121.0 |
C9—N2—N1 | 110.8 (2) | C18—C19—C20 | 119.3 (3) |
C16—N4—C20 | 115.6 (3) | C18—C19—H19A | 120.4 |
C16—N4—Ni1 | 121.7 (2) | C20—C19—H19A | 120.4 |
C20—N4—Ni1 | 122.7 (2) | N4—C20—C19 | 123.6 (3) |
C21—N5—C25 | 115.9 (3) | N4—C20—H20A | 118.2 |
C21—N5—Ni1 | 120.9 (2) | C19—C20—H20A | 118.2 |
C25—N5—Ni1 | 122.9 (2) | N5—C21—C22 | 123.8 (3) |
C30—N6—C26 | 117.0 (3) | N5—C21—H21A | 118.1 |
C30—N6—Ni1 | 121.4 (2) | C22—C21—H21A | 118.1 |
C26—N6—Ni1 | 121.5 (2) | C23—C22—C21 | 119.1 (4) |
C35—N7—C31 | 116.8 (6) | C23—C22—H22A | 120.4 |
O1—C1—C2 | 117.0 (3) | C21—C22—H22A | 120.4 |
O1—C1—C6 | 125.9 (2) | C24—C23—C22 | 117.8 (4) |
C2—C1—C6 | 117.1 (2) | C24—C23—H23A | 121.1 |
C3—C2—C1 | 123.8 (3) | C22—C23—H23A | 121.1 |
C3—C2—H2B | 118.1 | C23—C24—C25 | 120.3 (4) |
C1—C2—H2B | 118.1 | C23—C24—H24A | 119.9 |
C2—C3—C4 | 118.2 (3) | C25—C24—H24A | 119.9 |
C2—C3—H3A | 120.9 | N5—C25—C24 | 123.0 (4) |
C4—C3—H3A | 120.9 | N5—C25—H25A | 118.5 |
C5—C4—C3 | 120.8 (3) | C24—C25—H25A | 118.5 |
C5—C4—Cl1 | 120.5 (3) | N6—C26—C27 | 123.3 (3) |
C3—C4—Cl1 | 118.7 (2) | N6—C26—H26A | 118.4 |
C4—C5—C6 | 122.8 (3) | C27—C26—H26A | 118.4 |
C4—C5—H5A | 118.6 | C28—C27—C26 | 118.9 (3) |
C6—C5—H5A | 118.6 | C28—C27—H27A | 120.6 |
C5—C6—C1 | 117.3 (2) | C26—C27—H27A | 120.6 |
C5—C6—C7 | 117.7 (2) | C27—C28—C29 | 118.8 (3) |
C1—C6—C7 | 125.0 (2) | C27—C28—H28A | 120.6 |
N1—C7—C6 | 120.1 (2) | C29—C28—H28A | 120.6 |
N1—C7—C8 | 120.8 (2) | C28—C29—C30 | 118.8 (3) |
C6—C7—C8 | 119.1 (2) | C28—C29—H29A | 120.6 |
C7—C8—H8A | 109.5 | C30—C29—H29A | 120.6 |
C7—C8—H8B | 109.5 | N6—C30—C29 | 123.2 (3) |
H8A—C8—H8B | 109.5 | N6—C30—H30A | 118.4 |
C7—C8—H8C | 109.5 | C29—C30—H30A | 118.4 |
H8A—C8—H8C | 109.5 | C32—C31—N7 | 119.1 (6) |
H8B—C8—H8C | 109.5 | C32—C31—H31A | 120.4 |
O2—C9—N2 | 127.3 (2) | N7—C31—H31A | 120.4 |
O2—C9—C10 | 117.3 (2) | C31—C32—C33 | 120.9 (5) |
N2—C9—C10 | 115.4 (2) | C31—C32—H32A | 119.6 |
C11—C10—C15 | 119.1 (2) | C33—C32—H32A | 119.6 |
C11—C10—C9 | 119.1 (2) | C34—C33—C32 | 122.5 (5) |
C15—C10—C9 | 121.8 (2) | C34—C33—H33A | 118.8 |
C10—C11—C12 | 120.9 (3) | C32—C33—H33A | 118.8 |
C10—C11—H11A | 119.5 | C35—C34—C33 | 120.0 (6) |
C12—C11—H11A | 119.5 | C35—C34—H34A | 120.0 |
C13—C12—C11 | 118.5 (3) | C33—C34—H34A | 120.0 |
C13—C12—H12A | 120.8 | C34—C35—N7 | 120.7 (6) |
C11—C12—H12A | 120.8 | C34—C35—H35A | 119.7 |
C12—C13—C14 | 122.2 (3) | N7—C35—H35A | 119.7 |
N1—Ni1—O1—C1 | −8.7 (2) | C2—C1—C6—C5 | 0.9 (3) |
O2—Ni1—O1—C1 | −15.9 (6) | O1—C1—C6—C7 | 0.8 (4) |
N6—Ni1—O1—C1 | 170.8 (2) | C2—C1—C6—C7 | −179.4 (2) |
N4—Ni1—O1—C1 | −100.8 (2) | N2—N1—C7—C6 | −177.6 (2) |
N5—Ni1—O1—C1 | 85.1 (2) | Ni1—N1—C7—C6 | 3.4 (4) |
O1—Ni1—O2—C9 | 4.4 (5) | N2—N1—C7—C8 | 2.5 (3) |
N1—Ni1—O2—C9 | −2.93 (16) | Ni1—N1—C7—C8 | −176.48 (19) |
N6—Ni1—O2—C9 | 177.57 (16) | C5—C6—C7—N1 | 172.9 (2) |
N4—Ni1—O2—C9 | 89.53 (17) | C1—C6—C7—N1 | −6.8 (4) |
N5—Ni1—O2—C9 | −96.83 (16) | C5—C6—C7—C8 | −7.2 (4) |
O1—Ni1—N1—C7 | 3.0 (2) | C1—C6—C7—C8 | 173.1 (2) |
O2—Ni1—N1—C7 | −178.2 (2) | Ni1—O2—C9—N2 | 3.1 (3) |
N6—Ni1—N1—C7 | −171.7 (10) | Ni1—O2—C9—C10 | −177.29 (17) |
N4—Ni1—N1—C7 | 94.3 (2) | N1—N2—C9—O2 | −0.8 (3) |
N5—Ni1—N1—C7 | −89.2 (2) | N1—N2—C9—C10 | 179.53 (19) |
O1—Ni1—N1—N2 | −176.06 (15) | O2—C9—C10—C11 | 8.8 (4) |
O2—Ni1—N1—N2 | 2.73 (14) | N2—C9—C10—C11 | −171.6 (2) |
N6—Ni1—N1—N2 | 9.3 (12) | O2—C9—C10—C15 | −170.7 (2) |
N4—Ni1—N1—N2 | −84.68 (16) | N2—C9—C10—C15 | 9.0 (4) |
N5—Ni1—N1—N2 | 91.75 (16) | C15—C10—C11—C12 | 0.9 (4) |
C7—N1—N2—C9 | 178.8 (2) | C9—C10—C11—C12 | −178.6 (3) |
Ni1—N1—N2—C9 | −2.0 (2) | C10—C11—C12—C13 | 0.3 (5) |
O1—Ni1—N4—C16 | 6.9 (3) | C11—C12—C13—C14 | −0.8 (5) |
N1—Ni1—N4—C16 | −83.5 (3) | C11—C12—C13—N3 | 178.0 (3) |
O2—Ni1—N4—C16 | −163.6 (3) | C12—C13—C14—C15 | 0.2 (5) |
N6—Ni1—N4—C16 | 100.8 (3) | N3—C13—C14—C15 | −178.6 (3) |
N5—Ni1—N4—C16 | 128.0 (7) | C11—C10—C15—C14 | −1.5 (4) |
O1—Ni1—N4—C20 | −172.9 (3) | C9—C10—C15—C14 | 178.0 (3) |
N1—Ni1—N4—C20 | 96.7 (3) | C13—C14—C15—C10 | 1.0 (5) |
O2—Ni1—N4—C20 | 16.6 (3) | C12—C13—N3—O4 | −171.1 (3) |
N6—Ni1—N4—C20 | −79.0 (3) | C14—C13—N3—O4 | 7.7 (5) |
N5—Ni1—N4—C20 | −51.8 (8) | C12—C13—N3—O3 | 7.8 (5) |
O1—Ni1—N5—C21 | 165.8 (2) | C14—C13—N3—O3 | −173.4 (3) |
N1—Ni1—N5—C21 | −103.7 (3) | C20—N4—C16—C17 | 0.2 (5) |
O2—Ni1—N5—C21 | −23.6 (3) | Ni1—N4—C16—C17 | −179.6 (3) |
N6—Ni1—N5—C21 | 72.0 (3) | N4—C16—C17—C18 | 0.6 (6) |
N4—Ni1—N5—C21 | 44.7 (8) | C16—C17—C18—C19 | −0.7 (6) |
O1—Ni1—N5—C25 | −7.8 (3) | C17—C18—C19—C20 | 0.0 (7) |
N1—Ni1—N5—C25 | 82.8 (3) | C16—N4—C20—C19 | −0.9 (6) |
O2—Ni1—N5—C25 | 162.9 (3) | Ni1—N4—C20—C19 | 178.9 (3) |
N6—Ni1—N5—C25 | −101.6 (3) | C18—C19—C20—N4 | 0.8 (7) |
N4—Ni1—N5—C25 | −128.8 (7) | C25—N5—C21—C22 | −0.3 (5) |
O1—Ni1—N6—C30 | 173.3 (2) | Ni1—N5—C21—C22 | −174.3 (3) |
N1—Ni1—N6—C30 | −12.1 (12) | N5—C21—C22—C23 | −0.5 (6) |
O2—Ni1—N6—C30 | −5.5 (2) | C21—C22—C23—C24 | 1.3 (7) |
N4—Ni1—N6—C30 | 82.1 (2) | C22—C23—C24—C25 | −1.3 (8) |
N5—Ni1—N6—C30 | −94.8 (2) | C21—N5—C25—C24 | 0.3 (6) |
O1—Ni1—N6—C26 | −9.4 (2) | Ni1—N5—C25—C24 | 174.2 (4) |
N1—Ni1—N6—C26 | 165.2 (10) | C23—C24—C25—N5 | 0.5 (8) |
O2—Ni1—N6—C26 | 171.7 (2) | C30—N6—C26—C27 | −0.2 (5) |
N4—Ni1—N6—C26 | −100.7 (2) | Ni1—N6—C26—C27 | −177.6 (2) |
N5—Ni1—N6—C26 | 82.5 (2) | N6—C26—C27—C28 | 0.6 (5) |
Ni1—O1—C1—C2 | −171.49 (18) | C26—C27—C28—C29 | −1.1 (5) |
Ni1—O1—C1—C6 | 8.3 (4) | C27—C28—C29—C30 | 1.2 (6) |
O1—C1—C2—C3 | 179.0 (3) | C26—N6—C30—C29 | 0.4 (5) |
C6—C1—C2—C3 | −0.9 (4) | Ni1—N6—C30—C29 | 177.7 (3) |
C1—C2—C3—C4 | 0.1 (5) | C28—C29—C30—N6 | −0.9 (6) |
C2—C3—C4—C5 | 0.6 (5) | C35—N7—C31—C32 | −0.5 (9) |
C2—C3—C4—Cl1 | −179.3 (2) | N7—C31—C32—C33 | −1.4 (9) |
C3—C4—C5—C6 | −0.5 (4) | C31—C32—C33—C34 | 2.2 (9) |
Cl1—C4—C5—C6 | 179.4 (2) | C32—C33—C34—C35 | −1.0 (10) |
C4—C5—C6—C1 | −0.2 (4) | C33—C34—C35—N7 | −1.0 (9) |
C4—C5—C6—C7 | −180.0 (3) | C31—N7—C35—C34 | 1.7 (9) |
O1—C1—C6—C5 | −178.9 (2) |
Hydrogen-bond geometry (Å, º) top
D—H···A | D—H | H···A | D···A | D—H···A |
C8—H8A···N2 | 0.96 | 2.22 | 2.691 (3) | 109 |
C11—H11A···O2 | 0.93 | 2.44 | 2.762 (3) | 100 |
C16—H16A···O1 | 0.93 | 2.45 | 3.043 (4) | 121 |
C18—H18A···N2i | 0.93 | 2.58 | 3.500 (4) | 169 |
C20—H20A···O2 | 0.93 | 2.43 | 2.994 (4) | 119 |
C21—H21A···O2 | 0.93 | 2.47 | 3.044 (4) | 120 |
C25—H25A···O1 | 0.93 | 2.55 | 3.098 (4) | 118 |
C26—H26A···O1 | 0.93 | 2.47 | 3.053 (3) | 121 |
C30—H30A···O2 | 0.93 | 2.53 | 3.118 (3) | 122 |
Symmetry code: (i) x+1/2, −y+1/2, z−1/2. |
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