Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536807056966/sj2417sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S1600536807056966/sj2417Isup2.hkl |
CCDC reference: 672669
Key indicators
- Single-crystal X-ray study
- T = 139 K
- Mean (C-C) = 0.008 Å
- R factor = 0.049
- wR factor = 0.198
- Data-to-parameter ratio = 16.8
checkCIF/PLATON results
No syntax errors found
Alert level C RINTA01_ALERT_3_C The value of Rint is greater than 0.10 Rint given 0.108 PLAT020_ALERT_3_C The value of Rint is greater than 0.10 ......... 0.11 PLAT026_ALERT_3_C Ratio Observed / Unique Reflections too Low .... 47 Perc. PLAT042_ALERT_1_C Calc. and Rep. MoietyFormula Strings Differ .... ? PLAT152_ALERT_1_C Supplied and Calc Volume s.u. Inconsistent ..... ? PLAT341_ALERT_3_C Low Bond Precision on C-C Bonds (x 1000) Ang ... 8 PLAT716_ALERT_1_C H...A Unknown or Inconsistent Label .......... H1<I>N< PLAT716_ALERT_1_C H...A Unknown or Inconsistent Label .......... H4<I>N< PLAT790_ALERT_4_C Centre of Gravity not Within Unit Cell: Resd. # 2 C2 H6 O S
Alert level G PLAT794_ALERT_5_G Check Predicted Bond Valency for Ni1 (3) 2.96 PLAT860_ALERT_3_G Note: Number of Least-Squares Restraints ....... 2
0 ALERT level A = In general: serious problem 0 ALERT level B = Potentially serious problem 9 ALERT level C = Check and explain 2 ALERT level G = General alerts; check 4 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 5 ALERT type 3 Indicator that the structure quality may be low 1 ALERT type 4 Improvement, methodology, query or suggestion 1 ALERT type 5 Informative message, check
For the structure of 2'-[(5-chloro-1H-indol-3-yl)methylene]-2-(1H-indol-3-yl)acetohydrazide, see Ali et al. (2007).
2'-[(5-Chloro-1H-indol-3-yl)methylene]-2-(1H-indol-3-yl)acetohydrazide was synthesized by using a reported procedure (Ali et al., 2007). This compound (1 g, 2.85 mmol) and nickel acetate tetrahydrate (0.35 g, 1.42 mmol) were heated in ethanol (50 ml) for 5 h. The product that separated was collected and recrystallized from DMSO.
Carbon-bound H atoms were placed at calculated positions (C–H 0.95–0.99 Å), and were included in the refinement in the riding model approximation with U(H) set to 1.2–1.5Ueq(C). The amino hydrogen atom was located in a difference Fouier map, and was refined with a distance restraint of N–H 0.88±0.01 Å.
Data collection: APEX2 (Bruker, 2005); cell refinement: SAINT (Bruker, 2005); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: X-SEED (Barbour, 2001); software used to prepare material for publication: publCIF (Westrip, 2007).
[Ni(C19H14ClN4O)2]·2C2H6OS | F(000) = 948 |
Mr = 914.55 | Dx = 1.484 Mg m−3 |
Monoclinic, P21/c | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: -P 2ybc | Cell parameters from 1360 reflections |
a = 11.659 (1) Å | θ = 4.4–22.5° |
b = 10.219 (1) Å | µ = 0.76 mm−1 |
c = 17.585 (2) Å | T = 139 K |
β = 102.272 (3)° | Block, red |
V = 2047.2 (3) Å3 | 0.42 × 0.05 × 0.02 mm |
Z = 2 |
Bruker APEXII CCD diffractometer | 4683 independent reflections |
Radiation source: medium-focus sealed tube | 2216 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.108 |
ϕ and ω scans | θmax = 27.5°, θmin = 1.8° |
Absorption correction: multi-scan (SADABS; Sheldrick, 1996) | h = −15→14 |
Tmin = 0.776, Tmax = 0.985 | k = −13→10 |
13220 measured reflections | l = −22→22 |
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)] = 0.049 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.198 | H atoms treated by a mixture of independent and constrained refinement |
S = 0.99 | w = 1/[σ2(Fo2) + (0.076P)2] where P = (Fo2 + 2Fc2)/3 |
4683 reflections | (Δ/σ)max = 0.001 |
278 parameters | Δρmax = 0.50 e Å−3 |
2 restraints | Δρmin = −0.89 e Å−3 |
[Ni(C19H14ClN4O)2]·2C2H6OS | V = 2047.2 (3) Å3 |
Mr = 914.55 | Z = 2 |
Monoclinic, P21/c | Mo Kα radiation |
a = 11.659 (1) Å | µ = 0.76 mm−1 |
b = 10.219 (1) Å | T = 139 K |
c = 17.585 (2) Å | 0.42 × 0.05 × 0.02 mm |
β = 102.272 (3)° |
Bruker APEXII CCD diffractometer | 4683 independent reflections |
Absorption correction: multi-scan (SADABS; Sheldrick, 1996) | 2216 reflections with I > 2σ(I) |
Tmin = 0.776, Tmax = 0.985 | Rint = 0.108 |
13220 measured reflections |
R[F2 > 2σ(F2)] = 0.049 | 2 restraints |
wR(F2) = 0.198 | H atoms treated by a mixture of independent and constrained refinement |
S = 0.99 | Δρmax = 0.50 e Å−3 |
4683 reflections | Δρmin = −0.89 e Å−3 |
278 parameters |
x | y | z | Uiso*/Ueq | ||
Ni1 | 0.5000 | 0.5000 | 0.5000 | 0.0207 (3) | |
Cl1 | 0.77582 (14) | −0.23758 (13) | 0.53762 (9) | 0.0329 (4) | |
S1 | 0.21730 (14) | −0.18848 (14) | 0.10978 (9) | 0.0305 (4) | |
O1 | 0.3902 (3) | 0.5808 (3) | 0.4234 (2) | 0.0240 (9) | |
O2 | 0.2384 (3) | −0.0989 (4) | 0.1797 (2) | 0.0315 (10) | |
N1 | 0.4210 (4) | −0.0021 (5) | 0.2925 (3) | 0.0263 (11) | |
H1N | 0.369 (4) | −0.029 (6) | 0.252 (2) | 0.05 (2)* | |
N2 | 0.4846 (4) | 0.3641 (4) | 0.4281 (3) | 0.0214 (10) | |
N3 | 0.4110 (4) | 0.3933 (4) | 0.3554 (3) | 0.0242 (11) | |
N4 | −0.0266 (5) | 0.5368 (5) | 0.3064 (3) | 0.0289 (12) | |
H4N | −0.096 (2) | 0.499 (5) | 0.297 (4) | 0.040 (19)* | |
C1 | 0.5565 (5) | 0.0105 (5) | 0.4043 (3) | 0.0207 (12) | |
C2 | 0.6428 (5) | −0.0401 (5) | 0.4652 (3) | 0.0230 (13) | |
H2 | 0.6787 | 0.0131 | 0.5079 | 0.028* | |
C3 | 0.6737 (5) | −0.1689 (5) | 0.4610 (3) | 0.0262 (14) | |
C4 | 0.6230 (5) | −0.2500 (5) | 0.3983 (3) | 0.0276 (14) | |
H4 | 0.6474 | −0.3386 | 0.3976 | 0.033* | |
C5 | 0.5385 (5) | −0.2023 (5) | 0.3380 (3) | 0.0276 (14) | |
H5 | 0.5041 | −0.2560 | 0.2950 | 0.033* | |
C6 | 0.5055 (5) | −0.0719 (5) | 0.3425 (3) | 0.0230 (13) | |
C7 | 0.4171 (5) | 0.1210 (5) | 0.3197 (3) | 0.0240 (13) | |
H7 | 0.3657 | 0.1877 | 0.2950 | 0.029* | |
C8 | 0.4989 (5) | 0.1359 (5) | 0.3887 (3) | 0.0237 (13) | |
C9 | 0.5233 (5) | 0.2449 (5) | 0.4401 (3) | 0.0226 (13) | |
H9 | 0.5739 | 0.2285 | 0.4891 | 0.027* | |
C10 | 0.3674 (5) | 0.5089 (5) | 0.3609 (3) | 0.0223 (12) | |
C11 | 0.2836 (5) | 0.5632 (5) | 0.2906 (3) | 0.0243 (13) | |
H11A | 0.3127 | 0.6495 | 0.2774 | 0.029* | |
H11B | 0.2820 | 0.5041 | 0.2458 | 0.029* | |
C12 | 0.1612 (5) | 0.5787 (5) | 0.3033 (3) | 0.0224 (13) | |
C13 | 0.0737 (5) | 0.4888 (5) | 0.2867 (3) | 0.0252 (13) | |
H13 | 0.0806 | 0.4049 | 0.2648 | 0.030* | |
C14 | 0.1126 (5) | 0.6907 (5) | 0.3346 (3) | 0.0211 (12) | |
C15 | 0.1571 (5) | 0.8133 (5) | 0.3635 (3) | 0.0267 (14) | |
H15 | 0.2351 | 0.8379 | 0.3620 | 0.032* | |
C16 | 0.0856 (6) | 0.8971 (6) | 0.3938 (3) | 0.0331 (16) | |
H16 | 0.1152 | 0.9799 | 0.4134 | 0.040* | |
C17 | −0.0294 (6) | 0.8624 (5) | 0.3964 (3) | 0.0315 (15) | |
H17 | −0.0761 | 0.9212 | 0.4187 | 0.038* | |
C18 | −0.0766 (6) | 0.7439 (5) | 0.3671 (3) | 0.0291 (14) | |
H18 | −0.1554 | 0.7208 | 0.3675 | 0.035* | |
C19 | −0.0038 (5) | 0.6605 (5) | 0.3371 (3) | 0.0233 (13) | |
C20 | 0.1682 (6) | −0.0854 (6) | 0.0285 (4) | 0.0445 (18) | |
H20A | 0.2345 | −0.0345 | 0.0182 | 0.067* | |
H20B | 0.1080 | −0.0257 | 0.0396 | 0.067* | |
H20C | 0.1349 | −0.1388 | −0.0171 | 0.067* | |
C21 | 0.0809 (6) | −0.2677 (6) | 0.1102 (4) | 0.0408 (17) | |
H21A | 0.0888 | −0.3214 | 0.1572 | 0.061* | |
H21B | 0.0593 | −0.3236 | 0.0641 | 0.061* | |
H21C | 0.0198 | −0.2017 | 0.1095 | 0.061* |
U11 | U22 | U33 | U12 | U13 | U23 | |
Ni1 | 0.0197 (6) | 0.0166 (5) | 0.0232 (6) | 0.0004 (4) | −0.0016 (4) | −0.0016 (4) |
Cl1 | 0.0278 (9) | 0.0262 (8) | 0.0419 (9) | 0.0053 (6) | 0.0011 (7) | 0.0021 (6) |
S1 | 0.0267 (9) | 0.0282 (8) | 0.0343 (9) | 0.0030 (7) | 0.0017 (7) | −0.0093 (7) |
O1 | 0.024 (2) | 0.0199 (19) | 0.025 (2) | 0.0006 (17) | −0.0017 (18) | 0.0009 (16) |
O2 | 0.023 (2) | 0.037 (2) | 0.029 (2) | −0.0041 (19) | −0.0044 (19) | −0.0139 (18) |
N1 | 0.026 (3) | 0.026 (3) | 0.024 (3) | −0.004 (2) | −0.002 (2) | −0.007 (2) |
N2 | 0.016 (3) | 0.023 (2) | 0.025 (3) | −0.002 (2) | 0.003 (2) | −0.0009 (19) |
N3 | 0.025 (3) | 0.021 (2) | 0.023 (3) | 0.001 (2) | −0.003 (2) | 0.0013 (19) |
N4 | 0.023 (3) | 0.027 (3) | 0.036 (3) | −0.006 (2) | 0.002 (2) | −0.001 (2) |
C1 | 0.019 (3) | 0.018 (3) | 0.025 (3) | −0.004 (2) | 0.004 (2) | −0.005 (2) |
C2 | 0.018 (3) | 0.025 (3) | 0.025 (3) | −0.005 (2) | 0.000 (3) | −0.005 (2) |
C3 | 0.023 (3) | 0.023 (3) | 0.033 (3) | 0.000 (2) | 0.006 (3) | 0.001 (2) |
C4 | 0.028 (4) | 0.017 (3) | 0.041 (4) | −0.001 (3) | 0.013 (3) | −0.006 (3) |
C5 | 0.024 (3) | 0.025 (3) | 0.033 (3) | −0.009 (3) | 0.005 (3) | −0.010 (3) |
C6 | 0.015 (3) | 0.027 (3) | 0.024 (3) | −0.004 (2) | −0.001 (3) | 0.000 (2) |
C7 | 0.026 (3) | 0.022 (3) | 0.023 (3) | −0.006 (2) | 0.001 (3) | −0.001 (2) |
C8 | 0.025 (3) | 0.021 (3) | 0.023 (3) | −0.002 (2) | 0.001 (3) | −0.004 (2) |
C9 | 0.022 (3) | 0.019 (3) | 0.025 (3) | −0.002 (2) | 0.003 (3) | 0.000 (2) |
C10 | 0.017 (3) | 0.027 (3) | 0.021 (3) | −0.004 (2) | −0.001 (2) | 0.002 (2) |
C11 | 0.024 (3) | 0.025 (3) | 0.021 (3) | 0.003 (3) | −0.003 (3) | 0.000 (2) |
C12 | 0.023 (3) | 0.022 (3) | 0.019 (3) | 0.000 (2) | −0.002 (3) | 0.004 (2) |
C13 | 0.023 (3) | 0.024 (3) | 0.027 (3) | 0.001 (3) | 0.002 (3) | 0.002 (2) |
C14 | 0.021 (3) | 0.021 (3) | 0.018 (3) | −0.002 (2) | −0.001 (2) | 0.005 (2) |
C15 | 0.026 (3) | 0.024 (3) | 0.026 (3) | −0.003 (3) | −0.003 (3) | 0.004 (2) |
C16 | 0.041 (4) | 0.022 (3) | 0.032 (4) | −0.002 (3) | −0.002 (3) | 0.001 (3) |
C17 | 0.034 (4) | 0.028 (3) | 0.033 (4) | 0.010 (3) | 0.007 (3) | 0.003 (3) |
C18 | 0.024 (3) | 0.031 (3) | 0.031 (3) | 0.002 (3) | 0.003 (3) | 0.007 (3) |
C19 | 0.026 (3) | 0.020 (3) | 0.022 (3) | −0.002 (2) | 0.001 (3) | 0.006 (2) |
C20 | 0.058 (5) | 0.044 (4) | 0.030 (4) | −0.012 (4) | 0.007 (4) | −0.003 (3) |
C21 | 0.042 (4) | 0.040 (4) | 0.036 (4) | −0.017 (3) | −0.001 (3) | −0.001 (3) |
Ni1—O1 | 1.845 (4) | C7—C8 | 1.382 (7) |
Ni1—O1i | 1.845 (4) | C7—H7 | 0.9500 |
Ni1—N2i | 1.861 (4) | C8—C9 | 1.425 (7) |
Ni1—N2 | 1.861 (4) | C9—H9 | 0.9500 |
Cl1—C3 | 1.745 (6) | C10—C11 | 1.510 (7) |
S1—O2 | 1.510 (4) | C11—C12 | 1.499 (8) |
S1—C20 | 1.769 (6) | C11—H11A | 0.9900 |
S1—C21 | 1.786 (6) | C11—H11B | 0.9900 |
O1—C10 | 1.301 (6) | C12—C13 | 1.358 (7) |
N1—C7 | 1.351 (6) | C12—C14 | 1.438 (7) |
N1—C6 | 1.372 (7) | C13—H13 | 0.9500 |
N1—H1N | 0.88 (4) | C14—C19 | 1.402 (8) |
N2—C9 | 1.300 (6) | C14—C15 | 1.408 (7) |
N2—N3 | 1.413 (6) | C15—C16 | 1.379 (8) |
N3—C10 | 1.297 (6) | C15—H15 | 0.9500 |
N4—C19 | 1.378 (7) | C16—C17 | 1.398 (8) |
N4—C13 | 1.378 (7) | C16—H16 | 0.9500 |
N4—H4N | 0.88 (3) | C17—C18 | 1.383 (8) |
C1—C2 | 1.403 (7) | C17—H17 | 0.9500 |
C1—C6 | 1.403 (7) | C18—C19 | 1.384 (8) |
C1—C8 | 1.446 (7) | C18—H18 | 0.9500 |
C2—C3 | 1.370 (7) | C20—H20A | 0.9800 |
C2—H2 | 0.9500 | C20—H20B | 0.9800 |
C3—C4 | 1.405 (8) | C20—H20C | 0.9800 |
C4—C5 | 1.374 (8) | C21—H21A | 0.9800 |
C4—H4 | 0.9500 | C21—H21B | 0.9800 |
C5—C6 | 1.395 (7) | C21—H21C | 0.9800 |
C5—H5 | 0.9500 | ||
O1—Ni1—O1i | 180.000 (1) | C8—C9—H9 | 116.1 |
O1—Ni1—N2i | 96.52 (17) | N3—C10—O1 | 124.4 (5) |
O1i—Ni1—N2i | 83.48 (17) | N3—C10—C11 | 118.0 (5) |
O1—Ni1—N2 | 83.48 (17) | O1—C10—C11 | 117.6 (5) |
O1i—Ni1—N2 | 96.52 (17) | C12—C11—C10 | 112.9 (5) |
N2i—Ni1—N2 | 180.000 (1) | C12—C11—H11A | 109.0 |
O2—S1—C20 | 105.4 (3) | C10—C11—H11A | 109.0 |
O2—S1—C21 | 105.2 (3) | C12—C11—H11B | 109.0 |
C20—S1—C21 | 97.9 (3) | C10—C11—H11B | 109.0 |
C10—O1—Ni1 | 110.4 (3) | H11A—C11—H11B | 107.8 |
C7—N1—C6 | 109.3 (5) | C13—C12—C14 | 106.4 (5) |
C7—N1—H1N | 121 (4) | C13—C12—C11 | 126.3 (5) |
C6—N1—H1N | 129 (4) | C14—C12—C11 | 127.3 (5) |
C9—N2—N3 | 117.9 (4) | C12—C13—N4 | 110.1 (5) |
C9—N2—Ni1 | 127.5 (4) | C12—C13—H13 | 124.9 |
N3—N2—Ni1 | 114.2 (3) | N4—C13—H13 | 124.9 |
C10—N3—N2 | 107.2 (4) | C19—C14—C15 | 118.0 (5) |
C19—N4—C13 | 108.8 (5) | C19—C14—C12 | 107.4 (5) |
C19—N4—H4N | 125 (4) | C15—C14—C12 | 134.6 (5) |
C13—N4—H4N | 126 (4) | C16—C15—C14 | 119.1 (6) |
C2—C1—C6 | 119.1 (5) | C16—C15—H15 | 120.5 |
C2—C1—C8 | 134.5 (5) | C14—C15—H15 | 120.5 |
C6—C1—C8 | 106.3 (5) | C15—C16—C17 | 121.2 (6) |
C3—C2—C1 | 117.8 (5) | C15—C16—H16 | 119.4 |
C3—C2—H2 | 121.1 | C17—C16—H16 | 119.4 |
C1—C2—H2 | 121.1 | C18—C17—C16 | 121.2 (6) |
C2—C3—C4 | 122.5 (5) | C18—C17—H17 | 119.4 |
C2—C3—Cl1 | 119.3 (4) | C16—C17—H17 | 119.4 |
C4—C3—Cl1 | 118.2 (4) | C17—C18—C19 | 117.0 (6) |
C5—C4—C3 | 120.6 (5) | C17—C18—H18 | 121.5 |
C5—C4—H4 | 119.7 | C19—C18—H18 | 121.5 |
C3—C4—H4 | 119.7 | N4—C19—C18 | 129.2 (6) |
C4—C5—C6 | 117.1 (5) | N4—C19—C14 | 107.3 (5) |
C4—C5—H5 | 121.4 | C18—C19—C14 | 123.5 (5) |
C6—C5—H5 | 121.4 | S1—C20—H20A | 109.5 |
N1—C6—C5 | 129.0 (5) | S1—C20—H20B | 109.5 |
N1—C6—C1 | 108.2 (5) | H20A—C20—H20B | 109.5 |
C5—C6—C1 | 122.8 (5) | S1—C20—H20C | 109.5 |
N1—C7—C8 | 110.2 (5) | H20A—C20—H20C | 109.5 |
N1—C7—H7 | 124.9 | H20B—C20—H20C | 109.5 |
C8—C7—H7 | 124.9 | S1—C21—H21A | 109.5 |
C7—C8—C9 | 130.6 (5) | S1—C21—H21B | 109.5 |
C7—C8—C1 | 105.9 (5) | H21A—C21—H21B | 109.5 |
C9—C8—C1 | 123.4 (5) | S1—C21—H21C | 109.5 |
N2—C9—C8 | 127.8 (5) | H21A—C21—H21C | 109.5 |
N2—C9—H9 | 116.1 | H21B—C21—H21C | 109.5 |
N2i—Ni1—O1—C10 | 175.5 (4) | Ni1—N2—C9—C8 | 170.9 (5) |
N2—Ni1—O1—C10 | −4.5 (4) | C7—C8—C9—N2 | −10.9 (11) |
O1—Ni1—N2—C9 | −167.7 (5) | C1—C8—C9—N2 | 173.1 (6) |
O1i—Ni1—N2—C9 | 12.3 (5) | N2—N3—C10—O1 | 0.0 (7) |
O1—Ni1—N2—N3 | 4.7 (3) | N2—N3—C10—C11 | −179.2 (4) |
O1i—Ni1—N2—N3 | −175.3 (3) | Ni1—O1—C10—N3 | 3.8 (7) |
C9—N2—N3—C10 | 169.3 (5) | Ni1—O1—C10—C11 | −177.0 (4) |
Ni1—N2—N3—C10 | −3.8 (5) | N3—C10—C11—C12 | 113.6 (6) |
C6—C1—C2—C3 | 0.3 (8) | O1—C10—C11—C12 | −65.7 (6) |
C8—C1—C2—C3 | 177.8 (6) | C10—C11—C12—C13 | −91.7 (7) |
C1—C2—C3—C4 | 0.5 (9) | C10—C11—C12—C14 | 88.7 (7) |
C1—C2—C3—Cl1 | −177.1 (4) | C14—C12—C13—N4 | −0.6 (6) |
C2—C3—C4—C5 | −0.4 (9) | C11—C12—C13—N4 | 179.8 (5) |
Cl1—C3—C4—C5 | 177.3 (5) | C19—N4—C13—C12 | −0.5 (6) |
C3—C4—C5—C6 | −0.6 (9) | C13—C12—C14—C19 | 1.4 (6) |
C7—N1—C6—C5 | 179.2 (6) | C11—C12—C14—C19 | −178.9 (5) |
C7—N1—C6—C1 | 0.5 (7) | C13—C12—C14—C15 | 178.9 (6) |
C4—C5—C6—N1 | −177.1 (6) | C11—C12—C14—C15 | −1.4 (10) |
C4—C5—C6—C1 | 1.4 (9) | C19—C14—C15—C16 | 1.0 (8) |
C2—C1—C6—N1 | 177.5 (5) | C12—C14—C15—C16 | −176.3 (6) |
C8—C1—C6—N1 | −0.7 (6) | C14—C15—C16—C17 | 0.0 (8) |
C2—C1—C6—C5 | −1.3 (9) | C15—C16—C17—C18 | −1.4 (9) |
C8—C1—C6—C5 | −179.4 (5) | C16—C17—C18—C19 | 1.6 (8) |
C6—N1—C7—C8 | −0.2 (7) | C13—N4—C19—C18 | −177.5 (5) |
N1—C7—C8—C9 | −176.8 (6) | C13—N4—C19—C14 | 1.4 (6) |
N1—C7—C8—C1 | −0.2 (7) | C17—C18—C19—N4 | 178.2 (5) |
C2—C1—C8—C7 | −177.2 (6) | C17—C18—C19—C14 | −0.5 (8) |
C6—C1—C8—C7 | 0.6 (6) | C15—C14—C19—N4 | −179.7 (5) |
C2—C1—C8—C9 | −0.3 (10) | C12—C14—C19—N4 | −1.7 (6) |
C6—C1—C8—C9 | 177.4 (5) | C15—C14—C19—C18 | −0.8 (8) |
N3—N2—C9—C8 | −1.3 (9) | C12—C14—C19—C18 | 177.3 (5) |
Symmetry code: (i) −x+1, −y+1, −z+1. |
D—H···A | D—H | H···A | D···A | D—H···A |
N1—H1N···O2 | 0.88 (4) | 1.90 (5) | 2.766 (6) | 167 (6) |
N4—H4N···O2ii | 0.88 (3) | 2.05 (3) | 2.887 (6) | 158 (6) |
Symmetry code: (ii) −x, y+1/2, −z+1/2. |
Experimental details
Crystal data | |
Chemical formula | [Ni(C19H14ClN4O)2]·2C2H6OS |
Mr | 914.55 |
Crystal system, space group | Monoclinic, P21/c |
Temperature (K) | 139 |
a, b, c (Å) | 11.659 (1), 10.219 (1), 17.585 (2) |
β (°) | 102.272 (3) |
V (Å3) | 2047.2 (3) |
Z | 2 |
Radiation type | Mo Kα |
µ (mm−1) | 0.76 |
Crystal size (mm) | 0.42 × 0.05 × 0.02 |
Data collection | |
Diffractometer | Bruker APEXII CCD diffractometer |
Absorption correction | Multi-scan (SADABS; Sheldrick, 1996) |
Tmin, Tmax | 0.776, 0.985 |
No. of measured, independent and observed [I > 2σ(I)] reflections | 13220, 4683, 2216 |
Rint | 0.108 |
(sin θ/λ)max (Å−1) | 0.650 |
Refinement | |
R[F2 > 2σ(F2)], wR(F2), S | 0.049, 0.198, 0.99 |
No. of reflections | 4683 |
No. of parameters | 278 |
No. of restraints | 2 |
H-atom treatment | H atoms treated by a mixture of independent and constrained refinement |
Δρmax, Δρmin (e Å−3) | 0.50, −0.89 |
Computer programs: APEX2 (Bruker, 2005), SAINT (Bruker, 2005), SAINT, SHELXS97 (Sheldrick, 1997), SHELXL97 (Sheldrick, 1997), X-SEED (Barbour, 2001), publCIF (Westrip, 2007).
D—H···A | D—H | H···A | D···A | D—H···A |
N1—H1N···O2 | 0.88 (4) | 1.90 (5) | 2.766 (6) | 167 (6) |
N4—H4N···O2i | 0.88 (3) | 2.05 (3) | 2.887 (6) | 158 (6) |
Symmetry code: (i) −x, y+1/2, −z+1/2. |
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