Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536807022015/om2112sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S1600536807022015/om2112Isup2.hkl |
CCDC reference: 654693
Key indicators
- Single-crystal X-ray study
- T = 298 K
- Mean (C-C) = 0.013 Å
- R factor = 0.056
- wR factor = 0.164
- Data-to-parameter ratio = 14.0
checkCIF/PLATON results
No syntax errors found
Alert level C PLAT062_ALERT_4_C Rescale T(min) & T(max) by ..................... 0.98 PLAT125_ALERT_4_C No _symmetry_space_group_name_Hall Given ....... ? PLAT150_ALERT_1_C Volume as Calculated Differs from that Given ... 1951.40 Ang-3 PLAT230_ALERT_2_C Hirshfeld Test Diff for O1 - C6 .. 5.50 su PLAT241_ALERT_2_C Check High Ueq as Compared to Neighbors for N6 PLAT241_ALERT_2_C Check High Ueq as Compared to Neighbors for C9 PLAT242_ALERT_2_C Check Low Ueq as Compared to Neighbors for C16 PLAT242_ALERT_2_C Check Low Ueq as Compared to Neighbors for C17 PLAT341_ALERT_3_C Low Bond Precision on C-C Bonds (x 1000) Ang ... 13
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 25.01 From the CIF: _reflns_number_total 3427 Count of symmetry unique reflns 1981 Completeness (_total/calc) 172.99% TEST3: Check Friedels for noncentro structure Estimate of Friedel pairs measured 1446 Fraction of Friedel pairs measured 0.730 Are heavy atom types Z>Si present yes PLAT791_ALERT_1_G Confirm the Absolute Configuration of N2 = . S PLAT791_ALERT_1_G Confirm the Absolute Configuration of C6 = . S PLAT791_ALERT_1_G Confirm the Absolute Configuration of C8 = . S PLAT794_ALERT_5_G Check Predicted Bond Valency for Ni1 (2) 2.12
0 ALERT level A = In general: serious problem 0 ALERT level B = Potentially serious problem 9 ALERT level C = Check and explain 5 ALERT level G = General alerts; check 4 ALERT type 1 CIF construction/syntax error, inconsistent or missing data 5 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 3 ALERT type 4 Improvement, methodology, query or suggestion 1 ALERT type 5 Informative message, check
Data collection: SMART (Siemens, 1996); cell refinement: SMART; data reduction: SAINT (Siemens, 1996); 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.
[Ni(NCS)2(C15H16N4O)] | Dx = 1.509 Mg m−3 |
Mr = 443.19 | Mo Kα radiation, λ = 0.71073 Å |
Orthorhombic, P212121 | Cell parameters from 2405 reflections |
a = 8.524 (5) Å | θ = 2.4–20.7° |
b = 15.044 (9) Å | µ = 1.23 mm−1 |
c = 15.218 (9) Å | T = 298 K |
V = 1951.4 (19) Å3 | Block, red |
Z = 4 | 0.33 × 0.31 × 0.29 mm |
F(000) = 912 |
Bruker SMART 1000 CCD diffractometer | 3427 independent reflections |
Radiation source: fine-focus sealed tube | 2429 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.066 |
φ and ω scans | θmax = 25.0°, θmin = 1.9° |
Absorption correction: multi-scan (SADABS; Sheldrick, 1996) | h = −10→9 |
Tmin = 0.687, Tmax = 0.717 | k = −14→17 |
9991 measured reflections | l = −15→18 |
Refinement on F2 | Secondary atom site location: difference Fourier map |
Least-squares matrix: full | Hydrogen site location: inferred from neighbouring sites |
R[F2 > 2σ(F2)] = 0.056 | H-atom parameters constrained |
wR(F2) = 0.164 | w = 1/[σ2(Fo2) + (0.087P)2 + 1.7567P] where P = (Fo2 + 2Fc2)/3 |
S = 1.00 | (Δ/σ)max < 0.001 |
3427 reflections | Δρmax = 0.62 e Å−3 |
245 parameters | Δρmin = −0.36 e Å−3 |
0 restraints | Absolute structure: Flack (1983) |
Primary atom site location: structure-invariant direct methods | Absolute structure parameter: 0.02 (3) |
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. |
x | y | z | Uiso*/Ueq | ||
Ni1 | 0.78859 (11) | 0.11254 (6) | 0.22387 (6) | 0.0425 (3) | |
N1 | 0.8975 (7) | 0.0170 (4) | 0.1439 (4) | 0.0397 (14) | |
N2 | 0.9845 (7) | 0.1845 (4) | 0.1789 (4) | 0.0498 (15) | |
H2 | 0.9556 | 0.2215 | 0.1345 | 0.060* | |
N3 | 0.9235 (8) | 0.0752 (5) | 0.3344 (4) | 0.0506 (16) | |
N4 | 0.6419 (8) | 0.0192 (4) | 0.2822 (4) | 0.0480 (15) | |
N5 | 0.6420 (8) | 0.1409 (4) | 0.1199 (4) | 0.0546 (17) | |
N6 | 0.6941 (9) | 0.2139 (5) | 0.2976 (4) | 0.064 (2) | |
O1 | 1.1987 (5) | 0.1048 (3) | 0.2237 (3) | 0.0536 (12) | |
S1 | 0.4241 (3) | 0.16968 (18) | −0.01253 (14) | 0.0651 (6) | |
S2 | 0.5109 (4) | 0.31011 (17) | 0.41002 (15) | 0.0762 (8) | |
C1 | 0.8304 (10) | −0.0587 (5) | 0.1149 (5) | 0.053 (2) | |
H1 | 0.7284 | −0.0717 | 0.1325 | 0.064* | |
C2 | 0.9080 (10) | −0.1182 (6) | 0.0597 (5) | 0.063 (2) | |
H2A | 0.8618 | −0.1716 | 0.0431 | 0.076* | |
C3 | 1.0561 (12) | −0.0950 (6) | 0.0304 (6) | 0.075 (3) | |
H3 | 1.1097 | −0.1321 | −0.0082 | 0.089* | |
C4 | 1.1246 (12) | −0.0164 (6) | 0.0586 (7) | 0.074 (3) | |
H4 | 1.2256 | −0.0010 | 0.0411 | 0.089* | |
C5 | 1.0383 (9) | 0.0389 (5) | 0.1137 (4) | 0.0463 (19) | |
C6 | 1.1043 (9) | 0.1225 (6) | 0.1480 (5) | 0.057 (2) | |
H6 | 1.1683 | 0.1510 | 0.1026 | 0.068* | |
C7 | 1.0604 (12) | 0.2348 (6) | 0.2485 (6) | 0.073 (3) | |
H7A | 0.9842 | 0.2611 | 0.2881 | 0.088* | |
H7B | 1.1272 | 0.2813 | 0.2248 | 0.088* | |
C8 | 1.1569 (11) | 0.1622 (7) | 0.2942 (6) | 0.071 (3) | |
H8 | 1.2520 | 0.1885 | 0.3193 | 0.085* | |
C9 | 1.0731 (11) | 0.1124 (8) | 0.3627 (6) | 0.077 (3) | |
H9A | 1.1398 | 0.0643 | 0.3828 | 0.093* | |
H9B | 1.0546 | 0.1515 | 0.4122 | 0.093* | |
C10 | 0.8618 (11) | 0.0133 (6) | 0.3779 (6) | 0.064 (2) | |
H10 | 0.9143 | −0.0106 | 0.4260 | 0.077* | |
C11 | 0.7086 (12) | −0.0210 (5) | 0.3533 (5) | 0.055 (2) | |
C12 | 0.6357 (14) | −0.0892 (6) | 0.3975 (6) | 0.076 (3) | |
H12 | 0.6853 | −0.1170 | 0.4445 | 0.091* | |
C13 | 0.4893 (12) | −0.1155 (6) | 0.3717 (6) | 0.073 (3) | |
H13 | 0.4387 | −0.1618 | 0.4006 | 0.088* | |
C14 | 0.4166 (11) | −0.0726 (6) | 0.3017 (6) | 0.070 (3) | |
H14 | 0.3153 | −0.0877 | 0.2845 | 0.084* | |
C15 | 0.5000 (10) | −0.0064 (5) | 0.2580 (5) | 0.0529 (19) | |
H15 | 0.4538 | 0.0210 | 0.2097 | 0.064* | |
C16 | 0.5514 (9) | 0.1540 (5) | 0.0662 (5) | 0.0442 (17) | |
C17 | 0.6194 (10) | 0.2532 (5) | 0.3430 (6) | 0.054 (2) |
U11 | U22 | U33 | U12 | U13 | U23 | |
Ni1 | 0.0433 (5) | 0.0485 (5) | 0.0359 (5) | 0.0075 (4) | 0.0021 (5) | 0.0004 (5) |
N1 | 0.039 (4) | 0.038 (3) | 0.042 (3) | 0.001 (3) | 0.001 (3) | −0.001 (3) |
N2 | 0.050 (4) | 0.048 (4) | 0.052 (4) | 0.000 (3) | 0.000 (3) | 0.004 (3) |
N3 | 0.046 (4) | 0.069 (4) | 0.037 (3) | −0.002 (3) | −0.004 (3) | −0.008 (3) |
N4 | 0.046 (4) | 0.057 (4) | 0.040 (3) | 0.010 (3) | 0.011 (3) | −0.008 (3) |
N5 | 0.051 (4) | 0.058 (4) | 0.054 (4) | 0.014 (3) | 0.001 (4) | 0.004 (3) |
N6 | 0.073 (5) | 0.068 (5) | 0.050 (4) | 0.020 (4) | 0.015 (4) | −0.007 (3) |
O1 | 0.039 (3) | 0.076 (3) | 0.046 (3) | 0.017 (3) | −0.007 (3) | −0.008 (3) |
S1 | 0.0510 (13) | 0.0944 (17) | 0.0498 (12) | −0.0045 (12) | −0.0075 (10) | 0.0166 (12) |
S2 | 0.0984 (19) | 0.0755 (15) | 0.0548 (13) | 0.0334 (15) | 0.0133 (13) | −0.0014 (12) |
C1 | 0.056 (5) | 0.057 (5) | 0.047 (4) | −0.001 (4) | 0.007 (4) | 0.002 (4) |
C2 | 0.068 (6) | 0.058 (5) | 0.064 (5) | −0.010 (5) | 0.020 (4) | −0.024 (5) |
C3 | 0.087 (7) | 0.059 (6) | 0.078 (6) | 0.015 (5) | 0.041 (5) | −0.024 (5) |
C4 | 0.057 (6) | 0.071 (6) | 0.096 (7) | −0.002 (5) | 0.028 (5) | −0.018 (6) |
C5 | 0.054 (5) | 0.052 (5) | 0.033 (4) | −0.001 (4) | 0.010 (3) | 0.006 (3) |
C6 | 0.052 (5) | 0.064 (5) | 0.054 (5) | −0.009 (4) | 0.015 (4) | 0.000 (4) |
C7 | 0.092 (7) | 0.068 (6) | 0.059 (6) | −0.028 (5) | −0.003 (5) | −0.010 (4) |
C8 | 0.056 (5) | 0.087 (7) | 0.068 (6) | −0.017 (5) | −0.020 (4) | −0.012 (5) |
C9 | 0.080 (7) | 0.102 (7) | 0.049 (5) | −0.003 (6) | −0.025 (5) | 0.010 (5) |
C10 | 0.059 (6) | 0.082 (7) | 0.052 (5) | 0.008 (5) | −0.015 (4) | 0.006 (5) |
C11 | 0.074 (6) | 0.054 (5) | 0.038 (4) | 0.019 (5) | 0.012 (4) | 0.012 (3) |
C12 | 0.086 (7) | 0.069 (7) | 0.073 (6) | 0.008 (5) | 0.014 (6) | 0.023 (5) |
C13 | 0.073 (6) | 0.057 (5) | 0.089 (7) | 0.005 (6) | 0.017 (5) | 0.026 (5) |
C14 | 0.056 (5) | 0.072 (6) | 0.083 (7) | −0.006 (4) | 0.015 (5) | −0.008 (5) |
C15 | 0.051 (5) | 0.058 (5) | 0.050 (5) | 0.000 (4) | 0.009 (4) | 0.001 (4) |
C16 | 0.047 (4) | 0.041 (4) | 0.044 (4) | 0.003 (3) | 0.012 (4) | 0.003 (3) |
C17 | 0.056 (5) | 0.052 (5) | 0.053 (5) | 0.002 (4) | −0.002 (4) | 0.004 (4) |
Ni1—N6 | 2.058 (7) | C2—H2A | 0.9300 |
Ni1—N5 | 2.061 (7) | C3—C4 | 1.387 (13) |
Ni1—N4 | 2.079 (7) | C3—H3 | 0.9300 |
Ni1—N1 | 2.099 (6) | C4—C5 | 1.391 (11) |
Ni1—N2 | 2.104 (6) | C4—H4 | 0.9300 |
Ni1—N3 | 2.114 (6) | C5—C6 | 1.473 (11) |
N1—C5 | 1.327 (9) | C6—H6 | 0.9800 |
N1—C1 | 1.349 (9) | C7—C8 | 1.535 (13) |
N2—C7 | 1.453 (10) | C7—H7A | 0.9700 |
N2—C6 | 1.460 (10) | C7—H7B | 0.9700 |
N2—H2 | 0.9100 | C8—C9 | 1.468 (12) |
N3—C10 | 1.258 (11) | C8—H8 | 0.9800 |
N3—C9 | 1.457 (11) | C9—H9A | 0.9700 |
N4—C15 | 1.322 (10) | C9—H9B | 0.9700 |
N4—C11 | 1.365 (10) | C10—C11 | 1.453 (13) |
N5—C16 | 1.141 (9) | C10—H10 | 0.9300 |
N6—C17 | 1.110 (10) | C11—C12 | 1.375 (12) |
O1—C8 | 1.423 (10) | C12—C13 | 1.367 (14) |
O1—C6 | 1.429 (9) | C12—H12 | 0.9300 |
S1—C16 | 1.634 (8) | C13—C14 | 1.391 (12) |
S2—C17 | 1.621 (9) | C13—H13 | 0.9300 |
C1—C2 | 1.395 (11) | C14—C15 | 1.392 (11) |
C1—H1 | 0.9300 | C14—H14 | 0.9300 |
C2—C3 | 1.384 (12) | C15—H15 | 0.9300 |
N6—Ni1—N5 | 91.6 (3) | N1—C5—C6 | 115.7 (7) |
N6—Ni1—N4 | 91.8 (3) | C4—C5—C6 | 121.5 (8) |
N5—Ni1—N4 | 95.9 (3) | O1—C6—N2 | 104.6 (6) |
N6—Ni1—N1 | 175.2 (3) | O1—C6—C5 | 110.0 (7) |
N5—Ni1—N1 | 88.0 (2) | N2—C6—C5 | 113.1 (6) |
N4—Ni1—N1 | 92.9 (2) | O1—C6—H6 | 109.7 |
N6—Ni1—N2 | 96.1 (3) | N2—C6—H6 | 109.7 |
N5—Ni1—N2 | 97.2 (3) | C5—C6—H6 | 109.7 |
N4—Ni1—N2 | 164.4 (2) | N2—C7—C8 | 101.4 (7) |
N1—Ni1—N2 | 79.2 (2) | N2—C7—H7A | 111.5 |
N6—Ni1—N3 | 88.6 (3) | C8—C7—H7A | 111.5 |
N5—Ni1—N3 | 174.8 (3) | N2—C7—H7B | 111.5 |
N4—Ni1—N3 | 78.9 (3) | C8—C7—H7B | 111.5 |
N1—Ni1—N3 | 92.2 (2) | H7A—C7—H7B | 109.3 |
N2—Ni1—N3 | 87.9 (3) | O1—C8—C9 | 110.3 (8) |
C5—N1—C1 | 118.7 (7) | O1—C8—C7 | 102.9 (7) |
C5—N1—Ni1 | 115.5 (5) | C9—C8—C7 | 115.1 (8) |
C1—N1—Ni1 | 125.4 (5) | O1—C8—H8 | 109.4 |
C7—N2—C6 | 104.9 (7) | C9—C8—H8 | 109.4 |
C7—N2—Ni1 | 112.6 (5) | C7—C8—H8 | 109.4 |
C6—N2—Ni1 | 109.3 (4) | N3—C9—C8 | 114.4 (7) |
C7—N2—H2 | 110.0 | N3—C9—H9A | 108.7 |
C6—N2—H2 | 110.0 | C8—C9—H9A | 108.7 |
Ni1—N2—H2 | 110.0 | N3—C9—H9B | 108.7 |
C10—N3—C9 | 119.7 (7) | C8—C9—H9B | 108.7 |
C10—N3—Ni1 | 112.8 (6) | H9A—C9—H9B | 107.6 |
C9—N3—Ni1 | 127.5 (6) | N3—C10—C11 | 120.2 (8) |
C15—N4—C11 | 118.2 (7) | N3—C10—H10 | 119.9 |
C15—N4—Ni1 | 129.0 (6) | C11—C10—H10 | 119.9 |
C11—N4—Ni1 | 112.8 (6) | N4—C11—C12 | 122.1 (10) |
C16—N5—Ni1 | 174.6 (6) | N4—C11—C10 | 114.9 (7) |
C17—N6—Ni1 | 163.4 (8) | C12—C11—C10 | 123.0 (9) |
C8—O1—C6 | 110.8 (6) | C13—C12—C11 | 119.2 (9) |
N1—C1—C2 | 122.5 (8) | C13—C12—H12 | 120.4 |
N1—C1—H1 | 118.7 | C11—C12—H12 | 120.4 |
C2—C1—H1 | 118.7 | C12—C13—C14 | 119.5 (9) |
C3—C2—C1 | 117.7 (8) | C12—C13—H13 | 120.3 |
C3—C2—H2A | 121.1 | C14—C13—H13 | 120.3 |
C1—C2—H2A | 121.1 | C13—C14—C15 | 118.1 (9) |
C2—C3—C4 | 119.9 (8) | C13—C14—H14 | 121.0 |
C2—C3—H3 | 120.0 | C15—C14—H14 | 121.0 |
C4—C3—H3 | 120.0 | N4—C15—C14 | 122.9 (8) |
C3—C4—C5 | 118.3 (8) | N4—C15—H15 | 118.6 |
C3—C4—H4 | 120.9 | C14—C15—H15 | 118.6 |
C5—C4—H4 | 120.9 | N5—C16—S1 | 178.0 (7) |
N1—C5—C4 | 122.6 (7) | N6—C17—S2 | 179.5 (9) |
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