{N,N′-Bis­[3-methoxy­methyl-5-methyl­salicyl­idene]-(R,R)-1,2-di­phenyl­enedi­amino}nickel(II)

Wu, J.-C.; Tang, N.; Yu, K.-B.

doi:10.1107/S1600536803021949

{N,N'-Bis[3-methoxymethyl-5-methylsalicylidene]-(R,R)-1,2-diphenylenediamino}nickel(II)

In the title compound, 6,6'-bis(methoxymethyl)-4,4'-dimethyl-2,2'-[1,2-diphenyl-1,2-ethanediylbis(nitrilomethylidyne)]diphenol, [Ni(C₃₄H₃₄N₂O₄)], there are two independent molecules per asymmetric unit; both have a twofold axis. These molecular structures are two rotamers in the presence of steric repulsions between the ether groups, and the coordination geometry around the Ni^II atom is slightly tetrahedrally distorted square planar. The rotamers are stacked alternately along the c axis.

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Supporting information

	Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536803021949/ob6309sup1.cif Contains datablocks global, I
	Structure factor file (CIF format) https://doi.org/10.1107/S1600536803021949/ob6309Isup2.hkl Contains datablock I

CCDC reference: 195285

checkCIF report

Key indicators

Single-crystal X-ray study
T = 295 K
Mean (C-C) = 0.006 Å
R factor = 0.043
wR factor = 0.100
Data-to-parameter ratio = 19.3

checkCIF/PLATON results

No syntax errors found



Alert level B
PLAT111_ALERT_2_B ADDSYM Detects (Pseudo) Centre of Symmetry .....         95 PerFit
PLAT113_ALERT_2_B ADDSYM Suggests Possible Pseudo/New Spacegroup .       C2/c
PLAT230_ALERT_2_B Hirshfeld Test Diff for    O2     -   C17      =       9.80 su

Alert level C
PLAT125_ALERT_4_C No _symmetry_space_group_name_Hall Given .......          ?
PLAT220_ALERT_2_C Large Non-Solvent    C     Ueq(max)/Ueq(min) ...       3.01 Ratio
PLAT220_ALERT_2_C Large Non-Solvent    C     Ueq(max)/Ueq(min) ...       2.99 Ratio
PLAT222_ALERT_3_C Large Non-Solvent    H     Ueq(max)/Ueq(min) ...       3.02 Ratio
PLAT230_ALERT_2_C Hirshfeld Test Diff for    C1     -   C6       =       5.04 su
PLAT230_ALERT_2_C Hirshfeld Test Diff for    C11    -   C12      =       5.95 su
PLAT241_ALERT_2_C Check High   U(eq) as Compared to Neighbors ....        C21
PLAT242_ALERT_2_C Check Low    U(eq) as Compared to Neighbors ....        C23
PLAT411_ALERT_2_C Short Inter H...H Contact  H16A   ..  H22      =       2.14 Ang.
PLAT710_ALERT_4_C Delete 1-2-3 or 2-3-4 Linear Torsion Angle ... #          3
            N1  -NI1 -O1  -C14   111.00  3.00   2.655   1.555   1.555   1.555
PLAT710_ALERT_4_C Delete 1-2-3 or 2-3-4 Linear Torsion Angle ... #          4
            O1  -NI1 -N1  -C8     65.00  3.00   2.655   1.555   1.555   1.555
PLAT710_ALERT_4_C Delete 1-2-3 or 2-3-4 Linear Torsion Angle ... #          7
            O1  -NI1 -N1  -C7   -117.00  3.00   2.655   1.555   1.555   1.555
PLAT710_ALERT_4_C Delete 1-2-3 or 2-3-4 Linear Torsion Angle ... #         52
            N2  -NI2 -O3  -C31   -86.40  1.10   2.656   1.555   1.555   1.555
PLAT710_ALERT_4_C Delete 1-2-3 or 2-3-4 Linear Torsion Angle ... #         56
            O3  -NI2 -N2  -C25   -89.60  1.10   2.656   1.555   1.555   1.555
PLAT710_ALERT_4_C Delete 1-2-3 or 2-3-4 Linear Torsion Angle ... #         59
            O3  -NI2 -N2  -C24    81.80  1.10   2.656   1.555   1.555   1.555
PLAT742_ALERT_1_C Angle   Calc    126.1(4), Rep      126.12 ......    Missing su
              N1   -C8   -C9      1.555   1.555   1.555

Alert level G
REFLT03_ALERT_4_G Please check that the estimate of the number of Friedel pairs is
            correct. If it is not, please give the correct count in the
            _publ_section_exptl_refinement section of the submitted CIF.
           From the CIF: _diffrn_reflns_theta_max           28.25
           From the CIF: _reflns_number_total               7242
           Count of symmetry unique reflns         3769
           Completeness (_total/calc)            192.15%
           TEST3: Check Friedels for noncentro structure
           Estimate of Friedel pairs measured      3473
           Fraction of Friedel pairs measured     0.921
           Are heavy atom types Z>Si present          yes

   0 ALERT level A = In general: serious problem
   3 ALERT level B = Potentially serious problem
  16 ALERT level C = Check and explain
   1 ALERT level G = General alerts; check

   1 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
  10 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
   8 ALERT type 4 Improvement, methodology, query or suggestion

Computing details top

Data collection: XSCANS (Siemens, 1996); cell refinement: XSCANS; data reduction: SHELXTL (Siemens, 1996); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL.

6,6'-bis(methoxymethyl)-4,4'-dimethyl-2,2'-[1,2-diphenyl-1,2- ethanediylbis(nitrilomethylidyne)]diphenol top

Crystal data top

[Ni(C₃₄H₃₄N₂O₄)]	D_x = 1.346 Mg m⁻³
M_r = 593.34	Melting point: 512 K
Monoclinic, C2	Mo Kα radiation, λ = 0.71073 Å
a = 24.101 (3) Å	Cell parameters from 29 reflections
b = 13.760 (1) Å	θ = 3.0–14.2°
c = 8.989 (1) Å	µ = 0.70 mm⁻¹
β = 100.87 (1)°	T = 295 K
V = 2927.3 (5) Å³	Block, brown
Z = 4	0.52 × 0.40 × 0.32 mm
F(000) = 1248

Data collection top

Siemens P4 diffractometer	5073 reflections with I > 2σ(I)
Radiation source: normal-focus sealed tube	R_int = 0.014
Graphite monochromator	θ_max = 28.3°, θ_min = 1.7°
ω scans	h = −32→32
Absorption correction: ψ scan (SHELXTL; Siemens, 1996)	k = −18→18
T_min = 0.738, T_max = 0.798	l = −11→11
7965 measured reflections	3 standard reflections every 97 reflections
7242 independent reflections	intensity decay: 2.5%

Refinement top

Refinement on F²	Hydrogen site location: inferred from neighbouring sites
Least-squares matrix: full	H-atom parameters constrained
R[F² > 2σ(F²)] = 0.043	w = 1/[σ²(F_o²) + (0.0454P)²] where P = (F_o² + 2F_c²)/3
wR(F²) = 0.100	(Δ/σ)_max = 0.001
S = 0.96	Δρ_max = 0.47 e Å⁻³
7242 reflections	Δρ_min = −0.27 e Å⁻³
376 parameters	Extinction correction: SHELXTL, Fc^*=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4
1 restraint	Extinction coefficient: 0.00045 (13)
Primary atom site location: structure-invariant direct methods	Absolute structure: Flack (1983), 3473 Friedel pairs
Secondary atom site location: difference Fourier map	Absolute structure parameter: 0.038 (15)

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.

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.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å²) top

	x	y	z	U_iso*/U_eq
Ni1	0.5000	0.40797 (4)	0.0000	0.03748 (17)
O1	0.45311 (12)	0.5061 (2)	0.0383 (3)	0.0456 (8)
O2	0.34447 (15)	0.7422 (3)	0.0063 (4)	0.0870 (11)
N1	0.45378 (14)	0.3093 (2)	0.0494 (4)	0.0368 (8)
C1	0.46305 (15)	0.1038 (3)	0.2184 (4)	0.0514 (9)
H1	0.4874	0.1458	0.2803	0.062*
C2	0.44399 (17)	0.0202 (3)	0.2791 (5)	0.0664 (11)
H2	0.4555	0.0065	0.3816	0.080*
C3	0.4082 (2)	−0.0425 (3)	0.1883 (6)	0.0794 (15)
H3	0.3964	−0.0996	0.2282	0.095*
C4	0.3902 (2)	−0.0204 (3)	0.0403 (6)	0.0828 (16)
H4	0.3648	−0.0615	−0.0202	0.099*
C5	0.40903 (17)	0.0623 (3)	−0.0224 (5)	0.0613 (10)
H5	0.3967	0.0758	−0.1247	0.074*
C6	0.44610 (15)	0.1247 (3)	0.0665 (4)	0.0386 (9)
C7	0.46794 (12)	0.2120 (2)	−0.0077 (4)	0.0369 (7)
H7	0.4516	0.2093	−0.1161	0.044*
C8	0.41316 (18)	0.3195 (3)	0.1206 (5)	0.0414 (10)
H8	0.3975	0.2630	0.1516	0.050*
C9	0.38984 (13)	0.4082 (4)	0.1567 (4)	0.0403 (8)
C10	0.34386 (15)	0.4051 (4)	0.2335 (4)	0.0480 (9)
H10	0.3337	0.3465	0.2723	0.058*
C11	0.31377 (19)	0.4888 (4)	0.2514 (5)	0.0591 (13)
C12	0.32882 (18)	0.5761 (3)	0.1846 (4)	0.0513 (11)
H12	0.3074	0.6317	0.1903	0.062*
C13	0.37405 (17)	0.5810 (3)	0.1117 (4)	0.0454 (11)
C14	0.4080 (2)	0.4975 (3)	0.0995 (5)	0.0440 (11)
C15	0.2654 (2)	0.4865 (4)	0.3362 (5)	0.0890 (18)
H15A	0.2533	0.4205	0.3444	0.107*
H15B	0.2345	0.5243	0.2825	0.107*
H15C	0.2775	0.5131	0.4358	0.107*
C16	0.38927 (19)	0.6745 (3)	0.0398 (6)	0.0647 (14)
H16A	0.4205	0.7050	0.1076	0.078*
H16B	0.4022	0.6587	−0.0532	0.078*
C17	0.3089 (2)	0.7157 (5)	−0.1304 (5)	0.111 (2)
H17A	0.3312	0.7043	−0.2065	0.133*
H17B	0.2825	0.7672	−0.1627	0.133*
H17C	0.2887	0.6576	−0.1151	0.133*
Ni2	0.5000	0.41741 (3)	0.5000	0.03721 (16)
O3	0.54490 (12)	0.31790 (19)	0.4459 (3)	0.0431 (7)
O4	0.65755 (12)	0.0900 (2)	0.4908 (3)	0.0605 (8)
N2	0.53612 (15)	0.5161 (2)	0.4160 (4)	0.0395 (8)
C18	0.60015 (18)	0.7104 (3)	0.5019 (5)	0.0682 (12)
H18	0.6137	0.6622	0.5720	0.082*
C19	0.6321 (2)	0.7909 (4)	0.4920 (5)	0.0908 (17)
H19	0.6669	0.7972	0.5565	0.109*
C20	0.6141 (2)	0.8622 (4)	0.3898 (8)	0.094 (2)
H20	0.6362	0.9171	0.3846	0.113*
C21	0.5637 (2)	0.8521 (4)	0.2960 (8)	0.110 (2)
H21	0.5513	0.8997	0.2239	0.132*
C22	0.53021 (18)	0.7710 (3)	0.3063 (6)	0.0791 (14)
H22	0.4953	0.7658	0.2420	0.095*
C23	0.54741 (17)	0.6992 (3)	0.4083 (4)	0.0452 (10)
C24	0.51040 (14)	0.6139 (2)	0.4254 (4)	0.0396 (7)
H24	0.4771	0.6179	0.3440	0.047*
C25	0.57540 (17)	0.5054 (3)	0.3381 (5)	0.0433 (10)
H25	0.5855	0.5600	0.2882	0.052*
C26	0.60486 (14)	0.4167 (4)	0.3217 (4)	0.0420 (8)
C27	0.65167 (15)	0.4172 (4)	0.2493 (4)	0.0503 (9)
H27	0.6599	0.4747	0.2036	0.060*
C28	0.68538 (18)	0.3404 (3)	0.2416 (4)	0.0482 (10)
C29	0.67137 (17)	0.2567 (3)	0.3101 (4)	0.0504 (11)
H29	0.6939	0.2022	0.3067	0.060*
C30	0.62604 (17)	0.2480 (3)	0.3836 (4)	0.0466 (11)
C31	0.59050 (18)	0.3294 (3)	0.3862 (4)	0.0368 (10)
C32	0.73431 (18)	0.3447 (4)	0.1594 (5)	0.0704 (15)
H32A	0.7260	0.3902	0.0773	0.085*
H32B	0.7404	0.2815	0.1202	0.085*
H32C	0.7677	0.3651	0.2283	0.085*
C33	0.61270 (18)	0.1560 (3)	0.4595 (5)	0.0552 (12)
H33A	0.6010	0.1727	0.5538	0.066*
H33B	0.5810	0.1243	0.3951	0.066*
C34	0.69603 (19)	0.1142 (4)	0.6225 (5)	0.0797 (15)
H34A	0.7100	0.1788	0.6131	0.096*
H34B	0.7270	0.0691	0.6368	0.096*
H34C	0.6775	0.1113	0.7081	0.096*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Ni1	0.0341 (3)	0.0300 (4)	0.0488 (4)	0.000	0.0088 (3)	0.000
O1	0.0424 (17)	0.0320 (17)	0.0638 (19)	0.0014 (14)	0.0134 (15)	−0.0008 (15)
O2	0.088 (3)	0.060 (2)	0.117 (3)	0.0161 (19)	0.028 (2)	−0.002 (2)
N1	0.0352 (18)	0.0282 (15)	0.0476 (18)	0.0016 (12)	0.0094 (15)	0.0007 (14)
C1	0.047 (2)	0.044 (2)	0.067 (2)	0.0010 (16)	0.0187 (17)	0.0036 (18)
C2	0.079 (3)	0.060 (2)	0.068 (3)	0.017 (2)	0.033 (2)	0.024 (2)
C3	0.116 (4)	0.033 (2)	0.104 (4)	−0.007 (3)	0.059 (3)	0.004 (2)
C4	0.113 (4)	0.050 (3)	0.097 (4)	−0.038 (3)	0.050 (3)	−0.017 (3)
C5	0.078 (3)	0.046 (2)	0.063 (2)	−0.015 (2)	0.022 (2)	−0.0048 (19)
C6	0.041 (2)	0.0281 (19)	0.050 (2)	0.0001 (16)	0.0183 (17)	−0.0016 (15)
C7	0.0403 (17)	0.0286 (14)	0.0422 (17)	−0.0022 (13)	0.0092 (14)	0.0004 (14)
C8	0.037 (2)	0.036 (2)	0.054 (2)	−0.0011 (15)	0.0153 (18)	0.0063 (17)
C9	0.0379 (17)	0.0367 (19)	0.0470 (18)	0.007 (2)	0.0096 (14)	−0.005 (2)
C10	0.0461 (19)	0.046 (2)	0.056 (2)	0.003 (2)	0.0197 (16)	−0.002 (2)
C11	0.051 (3)	0.067 (3)	0.062 (3)	0.014 (3)	0.016 (2)	−0.009 (3)
C12	0.056 (3)	0.041 (2)	0.057 (3)	0.013 (2)	0.011 (2)	−0.002 (2)
C13	0.043 (2)	0.038 (2)	0.052 (2)	0.0098 (19)	−0.001 (2)	−0.0081 (19)
C14	0.043 (2)	0.037 (2)	0.049 (3)	0.002 (2)	0.002 (2)	−0.004 (2)
C15	0.081 (4)	0.092 (5)	0.107 (4)	0.014 (3)	0.050 (3)	0.008 (4)
C16	0.058 (3)	0.034 (2)	0.106 (4)	0.003 (2)	0.025 (3)	−0.001 (3)
C17	0.095 (4)	0.164 (7)	0.068 (3)	−0.028 (5)	−0.002 (3)	−0.004 (4)
Ni2	0.0401 (3)	0.0271 (3)	0.0467 (3)	0.000	0.0141 (3)	0.000
O3	0.0427 (17)	0.0289 (15)	0.0627 (17)	0.0027 (13)	0.0225 (15)	−0.0012 (13)
O4	0.071 (2)	0.0426 (17)	0.0685 (19)	0.0153 (15)	0.0150 (16)	0.0011 (15)
N2	0.0442 (17)	0.0311 (16)	0.0445 (19)	0.0034 (14)	0.0118 (14)	0.0024 (13)
C18	0.076 (3)	0.075 (3)	0.054 (2)	−0.027 (2)	0.011 (2)	0.007 (2)
C19	0.086 (4)	0.112 (4)	0.080 (3)	−0.058 (3)	0.029 (3)	−0.028 (3)
C20	0.094 (4)	0.044 (3)	0.166 (6)	−0.030 (3)	0.077 (5)	−0.017 (4)
C21	0.091 (4)	0.047 (3)	0.202 (7)	0.005 (3)	0.054 (4)	0.053 (4)
C22	0.056 (2)	0.054 (2)	0.126 (4)	0.004 (2)	0.015 (3)	0.040 (3)
C23	0.052 (2)	0.031 (2)	0.057 (2)	0.0008 (18)	0.0210 (19)	−0.0010 (17)
C24	0.0442 (18)	0.0282 (15)	0.0465 (18)	−0.0004 (13)	0.0089 (15)	0.0006 (14)
C25	0.050 (2)	0.0335 (19)	0.048 (2)	0.0014 (16)	0.0147 (18)	0.0056 (16)
C26	0.0451 (19)	0.041 (2)	0.0402 (17)	0.000 (2)	0.0094 (15)	0.003 (2)
C27	0.054 (2)	0.056 (2)	0.0437 (18)	0.005 (3)	0.0155 (17)	0.009 (3)
C28	0.047 (2)	0.053 (3)	0.047 (2)	0.008 (2)	0.0148 (19)	0.003 (2)
C29	0.046 (2)	0.054 (3)	0.054 (2)	0.017 (2)	0.017 (2)	−0.007 (2)
C30	0.049 (3)	0.042 (3)	0.050 (2)	0.004 (2)	0.013 (2)	−0.0024 (19)
C31	0.037 (2)	0.039 (2)	0.035 (2)	0.0016 (19)	0.0086 (17)	−0.0041 (17)
C32	0.062 (3)	0.080 (4)	0.080 (3)	0.021 (3)	0.041 (3)	0.010 (3)
C33	0.057 (3)	0.042 (3)	0.067 (3)	0.013 (2)	0.013 (2)	0.001 (2)
C34	0.066 (3)	0.083 (4)	0.087 (3)	0.018 (3)	0.007 (3)	0.002 (3)

Geometric parameters (Å, º) top

Ni1—O1ⁱ	1.835 (3)	C25—C26	1.434 (6)
Ni1—O1	1.835 (3)	C26—C27	1.404 (5)
Ni1—N1	1.862 (3)	C26—C31	1.405 (6)
Ni1—N1ⁱ	1.862 (3)	C27—C28	1.343 (6)
O1—C14	1.313 (5)	C28—C29	1.378 (6)
O2—C17	1.407 (5)	C28—C32	1.506 (5)
O2—C16	1.415 (5)	C29—C30	1.384 (5)
N1—C8	1.274 (5)	C30—C31	1.413 (6)
N1—C7	1.496 (4)	C30—C33	1.502 (6)
C1—C6	1.380 (5)	C1—H1	0.930
C1—C2	1.388 (5)	C2—H2	0.930
C2—C3	1.375 (6)	C3—H3	0.930
C3—C4	1.353 (6)	C4—H4	0.930
C4—C5	1.383 (5)	C5—H5	0.930
C5—C6	1.381 (5)	C7—H7	0.980
C6—C7	1.515 (5)	C8—H8	0.930
C7—C7ⁱ	1.525 (6)	C10—H10	0.930
C8—C9	1.407 (6)	C12—H12	0.930
C9—C10	1.412 (5)	C15—H15c	0.960
C9—C14	1.433 (6)	C15—H15b	0.961
C10—C11	1.387 (6)	C15—H15a	0.961
C11—C12	1.420 (6)	C16—H16a	0.970
C11—C15	1.510 (6)	C16—H16b	0.970
C12—C13	1.376 (6)	C17—H17a	0.959
C13—C14	1.426 (6)	C17—H17c	0.959
C13—C16	1.516 (6)	C17—H17b	0.960
Ni2—N2	1.849 (4)	C18—H18	0.931
Ni2—N2ⁱⁱ	1.849 (4)	C19—H19	0.929
Ni2—O3	1.866 (3)	C20—H20	0.931
Ni2—O3ⁱⁱ	1.866 (3)	C21—H21	0.930
O3—C31	1.320 (5)	C22—H22	0.929
O4—C33	1.399 (4)	C24—H24	0.980
O4—C34	1.399 (5)	C25—H25	0.931
N2—C25	1.288 (5)	C27—H27	0.930
N2—C24	1.491 (4)	C29—H29	0.930
C18—C19	1.362 (6)	C32—H32a	0.960
C18—C23	1.394 (5)	C32—H32b	0.960
C19—C20	1.358 (7)	C32—H32c	0.960
C20—C21	1.350 (7)	C33—H33a	0.970
C21—C22	1.391 (6)	C33—H33b	0.971
C22—C23	1.358 (5)	C34—H34a	0.960
C23—C24	1.500 (5)	C34—H34b	0.961
C24—C24ⁱⁱ	1.518 (6)	C34—H34c	0.961

O1ⁱ—Ni1—O1	85.22 (18)	O4—C33—C30	114.5 (4)
O1ⁱ—Ni1—N1	177.07 (17)	H1—C1—C6	119.88
O1—Ni1—N1	94.26 (11)	H1—C1—C2	119.88
O1ⁱ—Ni1—N1ⁱ	94.26 (11)	H2—C2—C3	119.84
O1—Ni1—N1ⁱ	177.07 (17)	H2—C2—C1	119.90
N1—Ni1—N1ⁱ	86.4 (2)	H3—C3—C4	120.26
C14—O1—Ni1	126.9 (3)	H3—C3—C2	120.30
C17—O2—C16	109.3 (4)	H4—C4—C3	119.45
C8—N1—C7	121.2 (3)	H4—C4—C5	119.48
C8—N1—Ni1	126.2 (3)	H5—C5—C6	119.96
C7—N1—Ni1	112.6 (2)	H5—C5—C4	119.91
C6—C1—C2	120.3 (4)	H7—C7—N1	107.46
C3—C2—C1	120.2 (4)	H7—C7—C6	107.43
C4—C3—C2	119.4 (4)	H7—C7—C7ⁱ	107.48
C3—C4—C5	121.1 (4)	H8—C8—N1	116.89
C6—C5—C4	120.1 (4)	H8—C8—C9	116.99
C1—C6—C5	118.7 (4)	N1—C8—C9	126.12
C1—C6—C7	122.6 (3)	H10—C10—C11	119.77
C5—C6—C7	118.6 (3)	H10—C10—C9	119.74
N1—C7—C6	115.9 (3)	H12—C12—C13	118.96
N1—C7—C7ⁱ	105.2 (2)	H12—C12—C11	118.94
C6—C7—C7ⁱ	113.0 (2)	H15c—C15—H15b	109.42
N1—C8—C9	126.2 (4)	H15c—C15—H15a	109.39
C8—C9—C10	118.1 (5)	H15c—C15—C11	109.59
C8—C9—C14	119.9 (3)	H15b—C15—H15a	109.43
C10—C9—C14	121.5 (4)	H15b—C15—C11	109.54
C11—C10—C9	120.5 (5)	H15a—C15—C11	109.46
C10—C11—C12	118.2 (4)	H16a—C16—H16b	107.52
C10—C11—C15	120.8 (5)	H16a—C16—O2	108.63
C12—C11—C15	121.0 (4)	H16a—C16—C13	108.71
C13—C12—C11	122.1 (4)	H16b—C16—O2	108.68
C12—C13—C14	121.0 (4)	H16b—C16—C13	108.67
C12—C13—C16	121.5 (4)	H17a—C17—H17c	109.49
C14—C13—C16	117.6 (4)	H17a—C17—H17b	109.49
O1—C14—C13	119.5 (4)	H17a—C17—O2	109.52
O1—C14—C9	124.1 (4)	H17c—C17—H17b	109.46
C13—C14—C9	116.4 (4)	H17c—C17—O2	109.44
O2—C16—C13	114.4 (4)	H17b—C17—O2	109.43
N2—Ni2—N2ⁱⁱ	85.5 (2)	H18—C18—C19	119.57
N2—Ni2—O3	95.25 (11)	H18—C18—C23	119.57
N2ⁱⁱ—Ni2—O3	170.48 (15)	H19—C19—C20	119.35
N2—Ni2—O3ⁱⁱ	170.48 (15)	H19—C19—C18	119.35
N2ⁱⁱ—Ni2—O3ⁱⁱ	95.25 (11)	H20—C20—C21	120.58
O3—Ni2—O3ⁱⁱ	85.58 (18)	H20—C20—C19	120.50
C31—O3—Ni2	125.9 (3)	H21—C21—C20	119.74
C33—O4—C34	112.3 (3)	H21—C21—C22	119.82
C25—N2—C24	119.3 (3)	H22—C22—C23	119.28
C25—N2—Ni2	126.1 (3)	H22—C22—C21	119.29
C24—N2—Ni2	114.0 (2)	H24—C24—N2	107.40
C19—C18—C23	120.8 (4)	H24—C24—C23	107.37
C20—C19—C18	121.4 (5)	H24—C24—C24	107.41
C21—C20—C19	118.9 (5)	H25—C25—N2	117.11
C20—C21—C22	120.4 (5)	H25—C25—C26	117.27
C23—C22—C21	121.4 (5)	H27—C27—C28	117.73
C22—C23—C18	117.1 (4)	H27—C27—C26	117.75
C22—C23—C24	121.8 (4)	H29—C29—C28	117.76
C18—C23—C24	121.1 (4)	H29—C29—C30	117.66
N2—C24—C23	116.1 (3)	H32a—C32—H32b	109.45
N2—C24—C24ⁱⁱ	105.1 (2)	H32a—C32—H32c	109.47
C23—C24—C24ⁱⁱ	113.1 (3)	H32a—C32—C28	109.49
N2—C25—C26	125.6 (4)	H32b—C32—H32c	109.51
C27—C26—C31	118.5 (5)	H32b—C32—C28	109.42
C27—C26—C25	120.0 (5)	H32c—C32—C28	109.48
C31—C26—C25	121.3 (3)	H33a—C33—H33b	107.56
C28—C27—C26	124.5 (5)	H33a—C33—O4	108.60
C27—C28—C29	115.7 (4)	H33a—C33—C30	108.65
C27—C28—C32	122.1 (4)	H33b—C33—O4	108.64
C29—C28—C32	122.2 (4)	H33b—C33—C30	108.65
C28—C29—C30	124.6 (4)	H34a—C34—H34b	109.48
C29—C30—C31	118.4 (4)	H34a—C34—H34c	109.44
C29—C30—C33	123.0 (4)	H34a—C34—O4	109.47
C31—C30—C33	118.6 (4)	H34b—C34—H34c	109.45
O3—C31—C26	124.0 (4)	H34b—C34—O4	109.50
O3—C31—C30	117.7 (4)	H34c—C34—O4	109.49
C26—C31—C30	118.2 (4)

O1ⁱ—Ni1—O1—C14	−169.3 (4)	N2—Ni2—O3—C31	7.7 (3)
N1—Ni1—O1—C14	7.8 (3)	N2ⁱⁱ—Ni2—O3—C31	−86.4 (11)
N1ⁱ—Ni1—O1—C14	111 (3)	O3ⁱⁱ—Ni2—O3—C31	178.1 (4)
O1ⁱ—Ni1—N1—C8	65 (3)	N2ⁱⁱ—Ni2—N2—C25	175.5 (5)
O1—Ni1—N1—C8	−14.9 (3)	O3—Ni2—N2—C25	5.0 (4)
N1ⁱ—Ni1—N1—C8	168.0 (4)	O3ⁱⁱ—Ni2—N2—C25	−89.6 (11)
O1ⁱ—Ni1—N1—C7	−117 (3)	N2ⁱⁱ—Ni2—N2—C24	−13.11 (17)
O1—Ni1—N1—C7	163.6 (3)	O3—Ni2—N2—C24	176.4 (3)
N1ⁱ—Ni1—N1—C7	−13.56 (16)	O3ⁱⁱ—Ni2—N2—C24	81.8 (11)
C6—C1—C2—C3	0.2 (6)	C23—C18—C19—C20	−0.9 (8)
C1—C2—C3—C4	−2.1 (7)	C18—C19—C20—C21	−0.5 (8)
C2—C3—C4—C5	2.5 (8)	C19—C20—C21—C22	1.5 (9)
C3—C4—C5—C6	−1.0 (7)	C20—C21—C22—C23	−1.2 (9)
C2—C1—C6—C5	1.4 (5)	C21—C22—C23—C18	−0.1 (7)
C2—C1—C6—C7	−176.7 (3)	C21—C22—C23—C24	177.0 (4)
C4—C5—C6—C1	−1.0 (6)	C19—C18—C23—C22	1.1 (6)
C4—C5—C6—C7	177.1 (4)	C19—C18—C23—C24	−176.0 (4)
C8—N1—C7—C6	−19.9 (5)	C25—N2—C24—C23	−27.6 (5)
Ni1—N1—C7—C6	161.6 (2)	Ni2—N2—C24—C23	160.3 (3)
C8—N1—C7—C7ⁱ	−145.4 (4)	C25—N2—C24—C24ⁱⁱ	−153.3 (4)
Ni1—N1—C7—C7ⁱ	36.0 (4)	Ni2—N2—C24—C24ⁱⁱ	34.6 (4)
C1—C6—C7—N1	−63.0 (4)	C22—C23—C24—N2	127.5 (4)
C5—C6—C7—N1	118.9 (4)	C18—C23—C24—N2	−55.6 (5)
C1—C6—C7—C7ⁱ	58.4 (5)	C22—C23—C24—C24ⁱⁱ	−111.0 (5)
C5—C6—C7—C7ⁱ	−119.6 (4)	C18—C23—C24—C24ⁱⁱ	66.0 (5)
C7—N1—C8—C9	−168.5 (3)	C24—N2—C25—C26	178.5 (3)
Ni1—N1—C8—C9	9.9 (6)	Ni2—N2—C25—C26	−10.5 (6)
N1—C8—C9—C10	178.5 (4)	N2—C25—C26—C27	−172.0 (4)
N1—C8—C9—C14	6.3 (6)	N2—C25—C26—C31	3.3 (6)
C8—C9—C10—C11	−170.1 (4)	C31—C26—C27—C28	−2.4 (6)
C14—C9—C10—C11	2.0 (6)	C25—C26—C27—C28	173.0 (4)
C9—C10—C11—C12	2.9 (6)	C26—C27—C28—C29	0.4 (6)
C9—C10—C11—C15	−178.7 (4)	C26—C27—C28—C32	178.6 (4)
C10—C11—C12—C13	−4.1 (7)	C27—C28—C29—C30	0.0 (7)
C15—C11—C12—C13	177.5 (4)	C32—C28—C29—C30	−178.2 (4)
C11—C12—C13—C14	0.3 (6)	C28—C29—C30—C31	1.6 (6)
C11—C12—C13—C16	179.5 (4)	C28—C29—C30—C33	−178.8 (4)
Ni1—O1—C14—C13	−175.8 (3)	Ni2—O3—C31—C26	−15.7 (6)
Ni1—O1—C14—C9	4.4 (6)	Ni2—O3—C31—C30	166.2 (3)
C12—C13—C14—O1	−175.4 (4)	C27—C26—C31—O3	−174.1 (3)
C16—C13—C14—O1	5.4 (6)	C25—C26—C31—O3	10.5 (6)
C12—C13—C14—C9	4.4 (6)	C27—C26—C31—C30	3.9 (5)
C16—C13—C14—C9	−174.8 (3)	C25—C26—C31—C30	−171.5 (3)
C8—C9—C14—O1	−13.8 (5)	C29—C30—C31—O3	174.6 (3)
C10—C9—C14—O1	174.3 (3)	C33—C30—C31—O3	−4.9 (6)
C8—C9—C14—C13	166.3 (4)	C29—C30—C31—C26	−3.6 (6)
C10—C9—C14—C13	−5.6 (5)	C33—C30—C31—C26	176.9 (3)
C17—O2—C16—C13	−80.6 (5)	C34—O4—C33—C30	80.5 (5)
C12—C13—C16—O2	−21.3 (6)	C29—C30—C33—O4	18.4 (6)
C14—C13—C16—O2	158.0 (4)	C31—C30—C33—O4	−162.1 (4)

Symmetry codes: (i) −x+1, y, −z; (ii) −x+1, y, −z+1.

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{N,N'-Bis­[3-methoxy­methyl-5-methyl­salicyl­idene]-(R,R)-1,2-di­phenyl­enedi­amino}nickel(II)

Supporting information

Key indicators

checkCIF/PLATON results

{N,N'-Bis[3-methoxymethyl-5-methylsalicylidene]-(R,R)-1,2-diphenylenediamino}nickel(II)