Download citation
Download citation
link to html
In the title complex, [Ni(C2N3)2(C13H8N2)2], which consists of discrete mol­ecules, the NiII atom has a slightly distorted octahedral environment, with four N atoms of two phenanthroline ligands and two terminal N atoms of two dicyan­amide ligands in a cis arrangement. The π–π stacking interactions result in the formation of a one-dimensional chain structure along the [110] direction.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536804004921/hb6020sup1.cif
Contains datablocks global, I

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536804004921/hb6020Isup2.hkl
Contains datablock I

CCDC reference: 238634

Key indicators

  • Single-crystal X-ray study
  • T = 293 K
  • Mean [sigma](C-C) = 0.003 Å
  • R factor = 0.069
  • wR factor = 0.157
  • Data-to-parameter ratio = 16.1

checkCIF/PLATON results

No syntax errors found



Alert level B PLAT230_ALERT_2_B Hirshfeld Test Diff for N6 - C25 .. 47.60 su PLAT230_ALERT_2_B Hirshfeld Test Diff for N6 - C26 .. 41.48 su PLAT230_ALERT_2_B Hirshfeld Test Diff for C23 - C24 .. 7.01 su PLAT241_ALERT_2_B Check High U(eq) as Compared to Neighbors .... N6 PLAT241_ALERT_2_B Check High U(eq) as Compared to Neighbors .... N9 PLAT242_ALERT_2_B Check Low U(eq) as Compared to Neighbors .... C26 PLAT242_ALERT_2_B Check Low U(eq) as Compared to Neighbors .... C28
Alert level C PLAT062_ALERT_4_C Rescale T(min) & T(max) by ..................... 0.85 PLAT220_ALERT_2_C Large Non-Solvent N Ueq(max)/Ueq(min) ... 2.74 Ratio PLAT230_ALERT_2_C Hirshfeld Test Diff for N3 - C13 .. 6.84 su PLAT230_ALERT_2_C Hirshfeld Test Diff for C16 - C17 .. 5.29 su PLAT230_ALERT_2_C Hirshfeld Test Diff for C17 - C18 .. 5.00 su PLAT230_ALERT_2_C Hirshfeld Test Diff for C19 - C20 .. 5.29 su PLAT242_ALERT_2_C Check Low U(eq) as Compared to Neighbors .... C25 PLAT242_ALERT_2_C Check Low U(eq) as Compared to Neighbors .... C27
Alert level G ABSTM02_ALERT_3_G When printed, the submitted absorption T values will be replaced by the scaled T values. Since the ratio of scaled T's is identical to the ratio of reported T values, the scaling does not imply a change to the absorption corrections used in the study. Ratio of Tmax expected/reported 0.848 Tmax scaled 0.848 Tmin scaled 0.809
0 ALERT level A = In general: serious problem 7 ALERT level B = Potentially serious problem 8 ALERT level C = Check and explain 1 ALERT level G = General alerts; check 0 ALERT type 1 CIF construction/syntax error, inconsistent or missing data 14 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 1 ALERT type 4 Improvement, methodology, query or suggestion

Computing details top

Data collection: CrystalClear (Rigaku Corporation, 2002); cell refinement: CrystalClear; data reduction: CrystalClear; program(s) used to solve structure: SHELXTL (Siemens, 1994); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL.

cis-Bis(dicyanamido)bis(1,10-phenanthroline)nickel(II) top
Crystal data top
[Ni(C2N3)2(C13H8N2)2]F(000) = 1128
Mr = 551.22Dx = 1.482 Mg m3
Monoclinic, P21/cMo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybcCell parameters from 4234 reflections
a = 9.580 (3) Åθ = 3.1–27.5°
b = 15.176 (5) ŵ = 0.83 mm1
c = 17.589 (6) ÅT = 293 K
β = 105.021 (4)°Prism, green
V = 2469.9 (13) Å30.32 × 0.23 × 0.20 mm
Z = 4
Data collection top
Rigaku Mercury CCD
diffractometer
5668 independent reflections
Radiation source: fine-focus sealed tube3542 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.056
ω scansθmax = 27.5°, θmin = 3.1°
Absorption correction: multi-scan
Sphere (CrystalClear; Rigaku Corporation, 2002)
h = 1212
Tmin = 0.955, Tmax = 1.000k = 1918
20640 measured reflectionsl = 2221
Refinement top
Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.069Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.158H-atom parameters constrained
S = 1.09 w = 1/[σ2(Fo2) + (0.056P)2 + 0.5P]
where P = (Fo2 + 2Fc2)/3
5668 reflections(Δ/σ)max = 0.004
352 parametersΔρmax = 0.89 e Å3
6 restraintsΔρmin = 0.63 e Å3
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
xyzUiso*/Ueq
Ni10.77384 (2)0.733262 (16)0.519212 (14)0.03916 (7)
N10.61658 (14)0.64276 (10)0.46436 (8)0.0393 (4)
N20.63813 (15)0.73377 (10)0.59621 (9)0.0412 (4)
C10.6086 (2)0.59610 (13)0.39958 (11)0.0484 (6)
H1A0.68810.59540.37850.058*
C20.4863 (2)0.54798 (14)0.36159 (13)0.0604 (7)
H2A0.48490.51650.31600.072*
C30.3693 (2)0.54748 (15)0.39164 (13)0.0653 (8)
H3A0.28710.51570.36680.078*
C40.3732 (2)0.59509 (14)0.46033 (13)0.0533 (7)
C50.2557 (2)0.59864 (17)0.49760 (14)0.0720 (8)
H5A0.16940.56990.47450.086*
C60.2690 (2)0.64225 (16)0.56418 (14)0.0707 (8)
H6A0.19120.64350.58660.085*
C70.39823 (19)0.68741 (14)0.60277 (12)0.0544 (6)
C80.4230 (2)0.73105 (15)0.67699 (14)0.0696 (7)
H8A0.35230.73070.70450.084*
C90.5504 (2)0.77313 (16)0.70715 (13)0.0692 (8)
H9A0.56750.80150.75560.083*
C100.6563 (2)0.77351 (14)0.66459 (11)0.0563 (7)
H10A0.74270.80310.68570.068*
C110.51390 (18)0.68961 (13)0.56694 (11)0.0437 (5)
C120.49988 (18)0.64137 (13)0.49497 (11)0.0416 (5)
N30.65123 (15)0.83910 (10)0.45747 (8)0.0415 (5)
N40.89448 (15)0.84074 (11)0.57313 (8)0.0444 (5)
C130.5312 (2)0.83752 (14)0.39978 (12)0.0519 (6)
H13A0.49040.78300.38280.062*
C140.4625 (2)0.91273 (14)0.36304 (13)0.0602 (7)
H14A0.37820.90800.32260.072*
C150.5189 (2)0.99254 (15)0.38648 (13)0.0658 (8)
H15A0.47371.04320.36230.079*
C160.6470 (2)0.99897 (13)0.44794 (12)0.0528 (6)
C170.7150 (2)1.07965 (15)0.47876 (14)0.0712 (8)
H17A0.67401.13270.45760.085*
C180.8359 (3)1.08095 (15)0.53731 (14)0.0741 (8)
H18A0.87771.13480.55570.089*
C190.9023 (2)1.00138 (14)0.57220 (12)0.0550 (6)
C201.0288 (3)0.99733 (16)0.63371 (13)0.0738 (8)
H20A1.07531.04910.65440.089*
C211.0842 (2)0.91842 (17)0.66329 (13)0.0701 (8)
H21A1.16790.91580.70430.084*
C221.0139 (2)0.84156 (15)0.63135 (12)0.0567 (7)
H22A1.05290.78790.65200.068*
C230.83823 (19)0.92100 (13)0.54389 (11)0.0448 (5)
C240.70778 (18)0.91922 (13)0.48160 (11)0.0440 (6)
N50.90131 (15)0.64119 (11)0.58980 (10)0.0526 (5)
N60.9908 (3)0.52241 (17)0.67871 (14)0.1077 (4)
N71.22950 (19)0.46457 (14)0.73626 (12)0.0770 (7)
C250.9516 (2)0.58819 (14)0.63073 (14)0.0590 (7)
C261.1230 (2)0.49371 (15)0.70726 (13)0.0579 (7)
N80.88112 (16)0.72493 (11)0.43260 (10)0.0521 (5)
N90.9711 (2)0.74532 (17)0.31737 (12)0.0969 (9)
N101.2172 (2)0.74706 (16)0.30464 (13)0.0961 (8)
C270.9309 (2)0.73243 (14)0.38090 (12)0.0526 (6)
C281.1053 (2)0.74467 (15)0.31489 (12)0.0617 (7)
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Ni10.03329 (10)0.04301 (13)0.04335 (12)0.00317 (11)0.01385 (9)0.00251 (11)
N10.0330 (7)0.0393 (9)0.0463 (8)0.0011 (7)0.0115 (6)0.0019 (7)
N20.0459 (7)0.0414 (9)0.0392 (8)0.0017 (7)0.0162 (6)0.0043 (7)
C10.0520 (10)0.0521 (12)0.0442 (10)0.0026 (9)0.0182 (8)0.0011 (9)
C20.0690 (13)0.0573 (14)0.0522 (12)0.0124 (11)0.0110 (11)0.0099 (11)
C30.0591 (12)0.0637 (15)0.0677 (15)0.0201 (11)0.0065 (12)0.0057 (12)
C40.0411 (9)0.0552 (13)0.0610 (13)0.0067 (10)0.0087 (9)0.0068 (10)
C50.0415 (10)0.0789 (17)0.0973 (18)0.0113 (11)0.0209 (11)0.0012 (14)
C60.0489 (9)0.0728 (16)0.1037 (16)0.0070 (11)0.0441 (10)0.0024 (13)
C70.0503 (9)0.0586 (13)0.0653 (11)0.0055 (10)0.0347 (8)0.0095 (10)
C80.0755 (12)0.0738 (15)0.0745 (13)0.0101 (12)0.0464 (10)0.0059 (12)
C90.0926 (14)0.0749 (16)0.0504 (11)0.0048 (13)0.0370 (10)0.0085 (11)
C100.0655 (12)0.0630 (14)0.0423 (11)0.0010 (11)0.0174 (10)0.0076 (10)
C110.0404 (8)0.0459 (11)0.0490 (10)0.0021 (9)0.0194 (8)0.0065 (9)
C120.0388 (8)0.0437 (11)0.0430 (10)0.0019 (8)0.0115 (8)0.0067 (9)
N30.0397 (7)0.0433 (9)0.0416 (8)0.0014 (7)0.0106 (7)0.0034 (7)
N40.0428 (7)0.0539 (10)0.0394 (8)0.0096 (7)0.0157 (6)0.0001 (7)
C130.0499 (10)0.0491 (12)0.0552 (12)0.0018 (10)0.0110 (9)0.0019 (10)
C140.0560 (11)0.0611 (14)0.0597 (13)0.0089 (11)0.0081 (11)0.0148 (11)
C150.0786 (14)0.0534 (13)0.0672 (14)0.0151 (12)0.0221 (12)0.0167 (11)
C160.0681 (11)0.0428 (12)0.0548 (11)0.0005 (10)0.0290 (9)0.0002 (9)
C170.0996 (16)0.0433 (13)0.0782 (15)0.0027 (12)0.0362 (13)0.0015 (12)
C180.1081 (15)0.0432 (13)0.0817 (15)0.0205 (12)0.0441 (13)0.0207 (11)
C190.0692 (11)0.0510 (12)0.0531 (11)0.0202 (10)0.0307 (9)0.0148 (10)
C200.0884 (14)0.0773 (16)0.0599 (13)0.0385 (13)0.0266 (12)0.0206 (12)
C210.0612 (12)0.0965 (18)0.0504 (13)0.0247 (13)0.0106 (11)0.0145 (13)
C220.0447 (10)0.0746 (15)0.0493 (12)0.0082 (11)0.0096 (9)0.0023 (11)
C230.0554 (9)0.0430 (11)0.0441 (10)0.0082 (9)0.0274 (8)0.0003 (8)
C240.0471 (9)0.0469 (11)0.0428 (10)0.0023 (9)0.0202 (8)0.0031 (9)
N50.0400 (8)0.0562 (10)0.0624 (10)0.0024 (8)0.0149 (7)0.0138 (9)
N60.1049 (6)0.1081 (6)0.1097 (6)0.0022 (5)0.0269 (5)0.0080 (5)
N70.0621 (11)0.0808 (14)0.0790 (14)0.0190 (10)0.0019 (11)0.0020 (11)
C250.0403 (9)0.0600 (13)0.0751 (14)0.0007 (10)0.0121 (10)0.0273 (11)
C260.0482 (11)0.0583 (14)0.0644 (13)0.0002 (10)0.0097 (10)0.0113 (11)
N80.0436 (7)0.0615 (11)0.0571 (9)0.0084 (8)0.0235 (7)0.0046 (8)
N90.0643 (11)0.178 (2)0.0546 (11)0.0322 (13)0.0266 (9)0.0045 (13)
N100.0813 (11)0.144 (2)0.0776 (13)0.0346 (12)0.0469 (10)0.0214 (13)
C270.0449 (9)0.0627 (13)0.0523 (11)0.0203 (10)0.0161 (9)0.0111 (10)
C280.0660 (11)0.0809 (16)0.0449 (11)0.0226 (11)0.0265 (9)0.0166 (10)
Geometric parameters (Å, º) top
Ni1—N52.0492 (16)N3—C241.354 (2)
Ni1—N82.0505 (19)N4—C221.323 (2)
Ni1—N42.0802 (16)N4—C231.377 (2)
Ni1—N12.0817 (14)C13—C141.391 (3)
Ni1—N22.1064 (17)C13—H13A0.9300
Ni1—N32.1162 (15)C14—C151.347 (3)
N1—C11.327 (2)C14—H14A0.9300
N1—C121.361 (2)C15—C161.413 (3)
N2—C101.316 (3)C15—H15A0.9300
N2—C111.346 (2)C16—C241.406 (3)
C1—C21.395 (3)C16—C171.426 (3)
C1—H1A0.9300C17—C181.336 (3)
C2—C31.357 (3)C17—H17A0.9300
C2—H2A0.9300C18—C191.427 (3)
C3—C41.400 (3)C18—H18A0.9300
C3—H3A0.9300C19—C231.398 (3)
C4—C121.398 (3)C19—C201.401 (3)
C4—C51.444 (3)C20—C211.358 (3)
C5—C61.322 (3)C20—H20A0.9300
C5—H5A0.9300C21—C221.391 (3)
C6—C71.424 (3)C21—H21A0.9300
C6—H6A0.9300C22—H22A0.9300
C7—C111.410 (3)C23—C241.433 (2)
C7—C81.428 (3)N5—C251.103 (3)
C8—C91.357 (3)N6—C251.298 (3)
C8—H8A0.9300N6—C261.311 (3)
C9—C101.409 (3)N7—C261.107 (3)
C9—H9A0.9300N8—C271.137 (3)
C10—H10A0.9300N9—C271.288 (3)
C11—C121.438 (3)N9—C281.298 (3)
N3—C131.322 (2)N10—C281.132 (3)
N5—Ni1—N894.21 (7)N1—C12—C4123.00 (18)
N5—Ni1—N494.88 (6)N1—C12—C11116.19 (15)
N8—Ni1—N493.49 (7)C4—C12—C11120.80 (18)
N5—Ni1—N194.41 (6)C13—N3—C24117.05 (16)
N8—Ni1—N193.26 (6)C13—N3—Ni1129.55 (13)
N4—Ni1—N1168.08 (6)C24—N3—Ni1113.39 (11)
N5—Ni1—N289.03 (7)C22—N4—C23117.20 (17)
N8—Ni1—N2171.73 (6)C22—N4—Ni1128.83 (14)
N4—Ni1—N293.82 (6)C23—N4—Ni1113.96 (11)
N1—Ni1—N278.89 (6)N3—C13—C14123.68 (19)
N5—Ni1—N3173.15 (6)N3—C13—H13A118.2
N8—Ni1—N389.08 (6)C14—C13—H13A118.2
N4—Ni1—N378.91 (6)C15—C14—C13119.46 (19)
N1—Ni1—N391.39 (6)C15—C14—H14A120.3
N2—Ni1—N388.52 (6)C13—C14—H14A120.3
C1—N1—C12117.43 (15)C14—C15—C16119.8 (2)
C1—N1—Ni1128.61 (13)C14—C15—H15A120.1
C12—N1—Ni1113.39 (12)C16—C15—H15A120.1
C10—N2—C11118.17 (18)C24—C16—C15116.45 (18)
C10—N2—Ni1129.17 (14)C24—C16—C17118.75 (17)
C11—N2—Ni1112.58 (12)C15—C16—C17124.77 (19)
N1—C1—C2123.04 (19)C18—C17—C16121.7 (2)
N1—C1—H1A118.5C18—C17—H17A119.2
C2—C1—H1A118.5C16—C17—H17A119.2
C3—C2—C1119.5 (2)C17—C18—C19121.3 (2)
C3—C2—H2A120.3C17—C18—H18A119.3
C1—C2—H2A120.3C19—C18—H18A119.3
C2—C3—C4119.51 (19)C23—C19—C20116.66 (19)
C2—C3—H3A120.2C23—C19—C18118.66 (18)
C4—C3—H3A120.2C20—C19—C18124.7 (2)
C12—C4—C3117.5 (2)C21—C20—C19120.6 (2)
C12—C4—C5118.3 (2)C21—C20—H20A119.7
C3—C4—C5124.15 (19)C19—C20—H20A119.7
C6—C5—C4120.88 (19)C20—C21—C22118.99 (19)
C6—C5—H5A119.6C20—C21—H21A120.5
C4—C5—H5A119.6C22—C21—H21A120.5
C5—C6—C7122.4 (2)N4—C22—C21123.5 (2)
C5—C6—H6A118.8N4—C22—H22A118.3
C7—C6—H6A118.8C21—C22—H22A118.3
C11—C7—C6119.0 (2)N4—C23—C19123.08 (16)
C11—C7—C8115.71 (18)N4—C23—C24116.63 (16)
C6—C7—C8125.3 (2)C19—C23—C24120.28 (17)
C9—C8—C7119.7 (2)N3—C24—C16123.57 (16)
C9—C8—H8A120.1N3—C24—C23117.10 (16)
C7—C8—H8A120.1C16—C24—C23119.31 (17)
C8—C9—C10119.5 (2)C25—N5—Ni1169.47 (17)
C8—C9—H9A120.2C25—N6—C26126.3 (2)
C10—C9—H9A120.2N5—C25—N6171.3 (2)
N2—C10—C9122.73 (19)N7—C26—N6173.1 (3)
N2—C10—H10A118.6C27—N8—Ni1169.47 (17)
C9—C10—H10A118.6C27—N9—C28123.33 (19)
N2—C11—C7124.06 (18)N8—C27—N9172.4 (2)
N2—C11—C12117.49 (17)N10—C28—N9172.6 (2)
C7—C11—C12118.45 (16)
 

Follow Acta Cryst. E
Sign up for e-alerts
Follow Acta Cryst. on Twitter
Follow us on facebook
Sign up for RSS feeds