In the title compound, [ZnCl
2(C
19H
13N
5)]·C
3H
7NO, the Zn
II cation shows distorted trigonal–bipyramidal coordination by three N atoms and two Cl atoms, the latter occupying equatorial sites. N—H
O and N—H
Cl hydrogen bonds help to stabilize the crystal packing.
Supporting information
CCDC reference: 252957
Key indicators
- Single-crystal X-ray study
- T = 295 K
- Mean (C-C) = 0.007 Å
- R factor = 0.050
- wR factor = 0.126
- Data-to-parameter ratio = 11.5
checkCIF/PLATON results
No syntax errors found
Alert level A
PLAT052_ALERT_1_A (Proper) Absorption Correction Method Missing .. ?
Alert level C
PLAT063_ALERT_3_C Crystal Probably too Large for Beam Size ....... 0.80 mm
PLAT164_ALERT_4_C Nr. of Refined C-H H-Atoms in Heavy-At Struct... 11
PLAT222_ALERT_3_C Large Non-Solvent H Ueq(max)/Ueq(min) ... 3.60 Ratio
PLAT244_ALERT_4_C Low Solvent U(eq) as Compared to Neighbors for N6
PLAT341_ALERT_3_C Low Bond Precision on C-C bonds (x 1000) Ang ... 7
PLAT350_ALERT_3_C Short C-H Bond (0.96A) C8 - H8 ... 0.77 Ang.
PLAT352_ALERT_3_C Short N-H Bond (0.87A) N3 - H3N ... 0.76 Ang.
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 0.920
Tmax scaled 0.760 Tmin scaled 0.723
1 ALERT level A = In general: serious problem
0 ALERT level B = Potentially serious problem
7 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
0 ALERT type 2 Indicator that the structure model may be wrong or deficient
6 ALERT type 3 Indicator that the structure quality may be low
2 ALERT type 4 Improvement, methodology, query or suggestion
Data collection: XSCANS (Siemens, 1996); cell refinement: XSCANS; data reduction: SHELXTL (Bruker, 1997); 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.
[2,6-Bis(1
H-benzimidazol-2-yl)pyridine]dichlorozinc(II)
N,
N-dimethylformamide solvate
top
Crystal data top
[ZnCl2(C19H13N5)]·C3H7NO | F(000) = 1064 |
Mr = 520.71 | Dx = 1.554 Mg m−3 |
Monoclinic, P21/n | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: -P 2yn | Cell parameters from 28 reflections |
a = 14.594 (3) Å | θ = 5.0–12.5° |
b = 7.889 (2) Å | µ = 1.37 mm−1 |
c = 19.811 (4) Å | T = 295 K |
β = 102.640 (8)° | Rod, light brown |
V = 2225.6 (9) Å3 | 0.80 × 0.20 × 0.20 mm |
Z = 4 | |
Data collection top
Bruker P4 diffractometer | 2705 reflections with I > 2σ(I) |
Radiation source: fine-focus sealed tube | Rint = 0.039 |
Graphite monochromator | θmax = 25.0°, θmin = 2.0° |
ω scans | h = −1→17 |
Absorption correction: ψ scan (XEMP in XSCANS; Siemens, 1996) | k = −1→9 |
Tmin = 0.723, Tmax = 0.760 | l = −23→23 |
5087 measured reflections | 3 standard reflections every 97 reflections |
3910 independent reflections | intensity decay: none |
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)] = 0.050 | Hydrogen site location: difference Fourier map |
wR(F2) = 0.126 | H atoms treated by a mixture of independent and constrained refinement |
S = 1.05 | w = 1/[σ2(Fo2) + (0.0475P)2 + 3.1157P] where P = (Fo2 + 2Fc2)/3 |
3910 reflections | (Δ/σ)max < 0.001 |
341 parameters | Δρmax = 0.51 e Å−3 |
0 restraints | Δρmin = −0.73 e Å−3 |
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 | Uiso*/Ueq | |
Zn | 0.29750 (3) | 0.75458 (8) | 0.01264 (2) | 0.03814 (18) | |
Cl1 | 0.16533 (9) | 0.6720 (2) | −0.06227 (6) | 0.0624 (4) | |
Cl2 | 0.28012 (9) | 0.99431 (19) | 0.07410 (7) | 0.0546 (4) | |
N1 | 0.4439 (2) | 0.6785 (5) | 0.04646 (17) | 0.0371 (9) | |
N2 | 0.3728 (2) | 0.8552 (5) | −0.06354 (17) | 0.0367 (9) | |
N3 | 0.5079 (3) | 0.8997 (6) | −0.0960 (2) | 0.0399 (10) | |
N4 | 0.3018 (2) | 0.5652 (5) | 0.09390 (17) | 0.0382 (10) | |
N5 | 0.3870 (3) | 0.4198 (6) | 0.18222 (19) | 0.0424 (10) | |
C1 | 0.4694 (3) | 0.5794 (6) | 0.1028 (2) | 0.0354 (11) | |
C2 | 0.5624 (3) | 0.5378 (7) | 0.1290 (3) | 0.0427 (13) | |
C3 | 0.6296 (3) | 0.5981 (8) | 0.0957 (3) | 0.0481 (14) | |
C4 | 0.6038 (3) | 0.6990 (7) | 0.0372 (3) | 0.0444 (13) | |
C5 | 0.5087 (3) | 0.7362 (6) | 0.0140 (2) | 0.0342 (10) | |
C6 | 0.4651 (3) | 0.8322 (6) | −0.0481 (2) | 0.0352 (11) | |
C7 | 0.4391 (3) | 0.9740 (7) | −0.1461 (2) | 0.0441 (13) | |
C8 | 0.4433 (5) | 1.0631 (8) | −0.2059 (3) | 0.0561 (16) | |
C9 | 0.3600 (5) | 1.1230 (9) | −0.2441 (3) | 0.0603 (17) | |
C10 | 0.2752 (5) | 1.0972 (8) | −0.2239 (3) | 0.0604 (16) | |
C11 | 0.2700 (4) | 1.0059 (8) | −0.1656 (3) | 0.0482 (13) | |
C12 | 0.3547 (3) | 0.9452 (7) | −0.1257 (2) | 0.0394 (12) | |
C13 | 0.3872 (3) | 0.5224 (7) | 0.1276 (2) | 0.0381 (11) | |
C14 | 0.2945 (3) | 0.3971 (7) | 0.1849 (2) | 0.0406 (12) | |
C15 | 0.2526 (4) | 0.3037 (8) | 0.2298 (3) | 0.0565 (16) | |
C16 | 0.1557 (4) | 0.3070 (9) | 0.2166 (3) | 0.0612 (17) | |
C17 | 0.1025 (4) | 0.3962 (8) | 0.1613 (3) | 0.0554 (15) | |
C18 | 0.1436 (3) | 0.4865 (7) | 0.1169 (3) | 0.0443 (12) | |
C19 | 0.2415 (3) | 0.4871 (6) | 0.1290 (2) | 0.0373 (11) | |
O | −0.0381 (3) | 0.8073 (6) | 0.22379 (19) | 0.0748 (13) | |
N6 | −0.0398 (3) | 0.8263 (7) | 0.1092 (2) | 0.0572 (12) | |
C20 | 0.0229 (6) | 0.9703 (10) | 0.1170 (4) | 0.103 (3) | |
H20A | 0.0434 | 0.9973 | 0.1652 | 0.155* | |
H20B | −0.0094 | 1.0659 | 0.0929 | 0.155* | |
H20C | 0.0764 | 0.9433 | 0.0981 | 0.155* | |
C21 | −0.0776 (5) | 0.7646 (10) | 0.0398 (3) | 0.095 (2) | |
H21A | −0.1184 | 0.6701 | 0.0417 | 0.143* | |
H21B | −0.0270 | 0.7294 | 0.0191 | 0.143* | |
H21C | −0.1124 | 0.8535 | 0.0125 | 0.143* | |
C22 | −0.0633 (4) | 0.7603 (8) | 0.1632 (3) | 0.0584 (15) | |
H22A | −0.1034 | 0.6674 | 0.1552 | 0.070* | |
H3N | 0.561 (3) | 0.904 (6) | −0.091 (2) | 0.033 (14)* | |
H5N | 0.443 (4) | 0.368 (9) | 0.211 (3) | 0.09 (2)* | |
H2 | 0.576 (3) | 0.472 (6) | 0.166 (2) | 0.035 (13)* | |
H3 | 0.694 (3) | 0.572 (6) | 0.113 (2) | 0.047 (13)* | |
H4 | 0.648 (3) | 0.747 (5) | 0.0113 (19) | 0.025 (10)* | |
H8 | 0.490 (3) | 1.078 (6) | −0.217 (2) | 0.034 (14)* | |
H9 | 0.359 (3) | 1.191 (7) | −0.281 (3) | 0.056 (16)* | |
H10 | 0.218 (4) | 1.131 (7) | −0.251 (3) | 0.058 (16)* | |
H11 | 0.212 (3) | 0.988 (6) | −0.151 (2) | 0.042 (13)* | |
H15 | 0.287 (4) | 0.262 (8) | 0.268 (3) | 0.08 (2)* | |
H16 | 0.128 (4) | 0.235 (7) | 0.247 (3) | 0.057 (15)* | |
H17 | 0.037 (4) | 0.389 (8) | 0.157 (3) | 0.075 (18)* | |
H18 | 0.110 (3) | 0.549 (6) | 0.081 (2) | 0.030 (12)* | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
Zn | 0.0305 (3) | 0.0495 (4) | 0.0327 (3) | −0.0012 (3) | 0.00311 (19) | 0.0016 (3) |
Cl1 | 0.0419 (7) | 0.0954 (12) | 0.0430 (7) | −0.0179 (7) | −0.0060 (5) | 0.0071 (8) |
Cl2 | 0.0449 (7) | 0.0595 (9) | 0.0631 (8) | −0.0011 (7) | 0.0201 (6) | −0.0115 (7) |
N1 | 0.0320 (19) | 0.050 (3) | 0.0287 (19) | −0.0055 (18) | 0.0045 (15) | −0.0040 (19) |
N2 | 0.033 (2) | 0.043 (3) | 0.033 (2) | −0.0035 (18) | 0.0058 (16) | −0.0031 (19) |
N3 | 0.032 (2) | 0.051 (3) | 0.040 (2) | −0.006 (2) | 0.0159 (19) | −0.004 (2) |
N4 | 0.035 (2) | 0.047 (3) | 0.0309 (19) | 0.0026 (19) | 0.0033 (16) | 0.0026 (19) |
N5 | 0.045 (2) | 0.047 (3) | 0.034 (2) | 0.007 (2) | 0.0065 (18) | 0.006 (2) |
C1 | 0.037 (2) | 0.040 (3) | 0.028 (2) | 0.000 (2) | 0.0049 (18) | −0.009 (2) |
C2 | 0.040 (3) | 0.045 (3) | 0.038 (3) | 0.003 (2) | −0.001 (2) | −0.003 (3) |
C3 | 0.031 (3) | 0.060 (4) | 0.049 (3) | 0.006 (3) | 0.000 (2) | −0.007 (3) |
C4 | 0.035 (3) | 0.054 (4) | 0.044 (3) | −0.007 (2) | 0.011 (2) | −0.013 (3) |
C5 | 0.040 (2) | 0.032 (3) | 0.032 (2) | −0.002 (2) | 0.0092 (18) | −0.009 (2) |
C6 | 0.038 (2) | 0.033 (3) | 0.035 (2) | −0.006 (2) | 0.009 (2) | −0.008 (2) |
C7 | 0.048 (3) | 0.055 (4) | 0.029 (2) | −0.004 (3) | 0.009 (2) | −0.005 (2) |
C8 | 0.069 (4) | 0.066 (4) | 0.041 (3) | −0.011 (3) | 0.027 (3) | −0.005 (3) |
C9 | 0.087 (5) | 0.063 (4) | 0.028 (3) | −0.005 (3) | 0.008 (3) | 0.007 (3) |
C10 | 0.064 (4) | 0.070 (4) | 0.037 (3) | −0.004 (3) | −0.012 (3) | −0.001 (3) |
C11 | 0.041 (3) | 0.058 (4) | 0.042 (3) | −0.009 (3) | 0.001 (2) | 0.000 (3) |
C12 | 0.042 (3) | 0.046 (3) | 0.028 (2) | −0.009 (2) | 0.005 (2) | −0.004 (2) |
C13 | 0.038 (2) | 0.048 (3) | 0.027 (2) | −0.001 (2) | 0.0040 (19) | 0.001 (2) |
C14 | 0.046 (3) | 0.043 (3) | 0.033 (2) | 0.000 (2) | 0.010 (2) | 0.003 (2) |
C15 | 0.064 (4) | 0.056 (4) | 0.049 (3) | 0.004 (3) | 0.011 (3) | 0.013 (3) |
C16 | 0.065 (4) | 0.068 (4) | 0.058 (3) | −0.002 (3) | 0.029 (3) | 0.012 (3) |
C17 | 0.047 (3) | 0.065 (4) | 0.059 (3) | −0.004 (3) | 0.022 (3) | −0.001 (3) |
C18 | 0.046 (3) | 0.046 (3) | 0.040 (3) | 0.000 (3) | 0.005 (2) | 0.000 (3) |
C19 | 0.041 (3) | 0.038 (3) | 0.034 (2) | −0.003 (2) | 0.010 (2) | −0.004 (2) |
O | 0.067 (3) | 0.104 (4) | 0.047 (2) | −0.024 (2) | −0.0007 (19) | −0.018 (2) |
N6 | 0.056 (3) | 0.059 (3) | 0.054 (3) | −0.006 (2) | 0.004 (2) | 0.009 (2) |
C20 | 0.118 (6) | 0.088 (6) | 0.100 (6) | −0.037 (5) | 0.014 (5) | 0.014 (5) |
C21 | 0.112 (6) | 0.113 (7) | 0.049 (3) | −0.008 (5) | −0.006 (4) | 0.005 (4) |
C22 | 0.048 (3) | 0.064 (4) | 0.057 (3) | −0.011 (3) | −0.001 (3) | 0.002 (3) |
Geometric parameters (Å, º) top
Zn—N1 | 2.179 (4) | C8—H8 | 0.78 (4) |
Zn—N4 | 2.187 (4) | C9—C10 | 1.396 (8) |
Zn—N2 | 2.201 (4) | C9—H9 | 0.90 (5) |
Zn—Cl1 | 2.2571 (13) | C10—C11 | 1.379 (8) |
Zn—Cl2 | 2.2933 (16) | C10—H10 | 0.93 (5) |
N1—C5 | 1.335 (5) | C11—C12 | 1.398 (7) |
N1—C1 | 1.346 (6) | C11—H11 | 0.96 (4) |
N2—C6 | 1.326 (5) | C14—C15 | 1.395 (7) |
N2—C12 | 1.395 (6) | C14—C19 | 1.398 (6) |
N3—C6 | 1.353 (6) | C15—C16 | 1.381 (8) |
N3—C7 | 1.379 (6) | C15—H15 | 0.88 (6) |
N3—H3N | 0.77 (4) | C16—C17 | 1.387 (8) |
N4—C13 | 1.322 (5) | C16—H16 | 0.97 (5) |
N4—C19 | 1.380 (6) | C17—C18 | 1.369 (7) |
N5—C13 | 1.352 (6) | C17—H17 | 0.95 (6) |
N5—C14 | 1.375 (6) | C18—C19 | 1.396 (6) |
N5—H5N | 0.98 (6) | C18—H18 | 0.92 (4) |
C1—C2 | 1.381 (6) | O—C22 | 1.233 (6) |
C1—C13 | 1.464 (6) | N6—C22 | 1.300 (7) |
C2—C3 | 1.381 (7) | N6—C20 | 1.446 (8) |
C2—H2 | 0.89 (4) | N6—C21 | 1.449 (7) |
C3—C4 | 1.389 (7) | C20—H20A | 0.9600 |
C3—H3 | 0.95 (5) | C20—H20B | 0.9600 |
C4—C5 | 1.394 (6) | C20—H20C | 0.9600 |
C4—H4 | 0.98 (4) | C21—H21A | 0.9600 |
C5—C6 | 1.466 (6) | C21—H21B | 0.9600 |
C7—C8 | 1.390 (7) | C21—H21C | 0.9600 |
C7—C12 | 1.398 (6) | C22—H22A | 0.9300 |
C8—C9 | 1.369 (8) | | |
| | | |
N1—Zn—N4 | 73.57 (14) | C8—C9—H9 | 121 (3) |
N1—Zn—N2 | 72.94 (13) | C10—C9—H9 | 117 (3) |
N4—Zn—N2 | 144.38 (14) | C11—C10—C9 | 122.1 (6) |
N1—Zn—Cl1 | 139.64 (11) | C11—C10—H10 | 115 (3) |
N4—Zn—Cl1 | 99.76 (11) | C9—C10—H10 | 123 (3) |
N2—Zn—Cl1 | 97.85 (10) | C10—C11—C12 | 116.7 (5) |
N1—Zn—Cl2 | 106.19 (11) | C10—C11—H11 | 123 (3) |
N4—Zn—Cl2 | 99.29 (11) | C12—C11—H11 | 121 (3) |
N2—Zn—Cl2 | 101.33 (11) | N2—C12—C7 | 109.2 (4) |
Cl1—Zn—Cl2 | 114.16 (6) | N2—C12—C11 | 130.3 (4) |
C5—N1—C1 | 120.1 (4) | C7—C12—C11 | 120.5 (4) |
C5—N1—Zn | 120.5 (3) | N4—C13—N5 | 113.0 (4) |
C1—N1—Zn | 119.3 (3) | N4—C13—C1 | 120.2 (4) |
C6—N2—C12 | 105.1 (4) | N5—C13—C1 | 126.8 (4) |
C6—N2—Zn | 115.3 (3) | N5—C14—C15 | 131.7 (5) |
C12—N2—Zn | 139.6 (3) | N5—C14—C19 | 106.3 (4) |
C6—N3—C7 | 107.3 (4) | C15—C14—C19 | 122.0 (5) |
C6—N3—H3N | 123 (3) | C16—C15—C14 | 116.3 (5) |
C7—N3—H3N | 129 (4) | C16—C15—H15 | 123 (4) |
C13—N4—C19 | 105.4 (4) | C14—C15—H15 | 120 (4) |
C13—N4—Zn | 114.7 (3) | C15—C16—C17 | 122.2 (5) |
C19—N4—Zn | 139.2 (3) | C15—C16—H16 | 115 (3) |
C13—N5—C14 | 106.5 (4) | C17—C16—H16 | 123 (3) |
C13—N5—H5N | 125 (4) | C18—C17—C16 | 121.5 (5) |
C14—N5—H5N | 129 (4) | C18—C17—H17 | 123 (4) |
N1—C1—C2 | 121.3 (4) | C16—C17—H17 | 115 (4) |
N1—C1—C13 | 111.0 (4) | C17—C18—C19 | 117.9 (5) |
C2—C1—C13 | 127.6 (4) | C17—C18—H18 | 123 (3) |
C3—C2—C1 | 118.7 (5) | C19—C18—H18 | 119 (3) |
C3—C2—H2 | 123 (3) | N4—C19—C18 | 131.0 (4) |
C1—C2—H2 | 118 (3) | N4—C19—C14 | 108.8 (4) |
C2—C3—C4 | 120.3 (5) | C18—C19—C14 | 120.1 (4) |
C2—C3—H3 | 120 (3) | C22—N6—C20 | 120.1 (5) |
C4—C3—H3 | 120 (3) | C22—N6—C21 | 122.2 (5) |
C3—C4—C5 | 117.7 (5) | C20—N6—C21 | 117.7 (5) |
C3—C4—H4 | 125 (2) | N6—C20—H20A | 109.5 |
C5—C4—H4 | 118 (2) | N6—C20—H20B | 109.5 |
N1—C5—C4 | 121.9 (4) | H20A—C20—H20B | 109.5 |
N1—C5—C6 | 110.9 (4) | N6—C20—H20C | 109.5 |
C4—C5—C6 | 127.2 (4) | H20A—C20—H20C | 109.5 |
N2—C6—N3 | 112.7 (4) | H20B—C20—H20C | 109.5 |
N2—C6—C5 | 119.8 (4) | N6—C21—H21A | 109.5 |
N3—C6—C5 | 127.5 (4) | N6—C21—H21B | 109.5 |
N3—C7—C8 | 131.9 (5) | H21A—C21—H21B | 109.5 |
N3—C7—C12 | 105.7 (4) | N6—C21—H21C | 109.5 |
C8—C7—C12 | 122.4 (5) | H21A—C21—H21C | 109.5 |
C9—C8—C7 | 116.5 (5) | H21B—C21—H21C | 109.5 |
C9—C8—H8 | 121 (4) | O—C22—N6 | 127.2 (6) |
C7—C8—H8 | 122 (4) | O—C22—H22A | 116.4 |
C8—C9—C10 | 121.8 (5) | N6—C22—H22A | 116.4 |
Hydrogen-bond geometry (Å, º) top
D—H···A | D—H | H···A | D···A | D—H···A |
N3—H3N···Cl2i | 0.76 (5) | 2.41 (4) | 3.142 (5) | 163 (5) |
N5—H5N···Oii | 0.98 (6) | 1.74 (6) | 2.706 (6) | 167 (5) |
C20—H20A···O | 0.96 | 2.37 | 2.783 (9) | 105 |
Symmetry codes: (i) −x+1, −y+2, −z; (ii) −x+1/2, y−1/2, −z+1/2. |