The title compound, [CoCl
2(C
11H
14N
2O)
2], was synthesized from 1-(2-ethoxyethyl)benzimidazole and cobalt dichloride in ethanol. The Co
II atom is coordinated in a distorted tetrahedral environment by two Cl atoms and two N atoms. The crystal structure is stabilized by intermolecular C—H
Cl and C—H
O interactions.
Supporting information
CCDC reference: 251580
Key indicators
- Single-crystal X-ray study
- T = 150 K
- Mean (C-C) = 0.004 Å
- R factor = 0.030
- wR factor = 0.073
- Data-to-parameter ratio = 20.6
checkCIF/PLATON results
No syntax errors found
Alert level A
PLAT220_ALERT_2_A Large Non-Solvent C Ueq(max)/Ueq(min) ... 4.80 Ratio
PLAT222_ALERT_3_A Large Non-Solvent H Ueq(max)/Ueq(min) ... 5.68 Ratio
Alert level C
PLAT063_ALERT_3_C Crystal Probably too Large for Beam Size ....... 0.64 mm
PLAT360_ALERT_2_C Short C(sp3)-C(sp3) Bond C21 - C22 ... 1.42 Ang.
PLAT850_ALERT_2_C Check Flack Parameter Exact Value 0.00 and su .. 0.00
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 28.31
From the CIF: _reflns_number_total 5762
Count of symmetry unique reflns 3074
Completeness (_total/calc) 187.44%
TEST3: Check Friedels for noncentro structure
Estimate of Friedel pairs measured 2688
Fraction of Friedel pairs measured 0.874
Are heavy atom types Z>Si present yes
2 ALERT level A = In general: serious problem
0 ALERT level B = Potentially serious problem
3 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
3 ALERT type 2 Indicator that the structure model may be wrong or deficient
2 ALERT type 3 Indicator that the structure quality may be low
1 ALERT type 4 Improvement, methodology, query or suggestion
Data collection: X-AREA (Stoe & Cie, 2002); cell refinement: X-AREA; data reduction: X-RED32 (Stoe & Cie, 2002); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEPIII (Farrugia, 1997); software used to prepare material for publication: WinGX (Farrugia, 1999).
Dichlorobis[1-(2-ethoxyethyl)-1
H-benzimidazole-
κN3]cobalt(II)
top
Crystal data top
[CoCl2(C11H14N2O)2] | F(000) = 1060 |
Mr = 510.31 | Dx = 1.413 Mg m−3 |
Orthorhombic, Pca21 | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: P 2c -2ac | Cell parameters from 5762 reflections |
a = 17.5842 (17) Å | θ = 1.6–28.4° |
b = 7.6235 (8) Å | µ = 0.96 mm−1 |
c = 17.8892 (13) Å | T = 150 K |
V = 2398.1 (4) Å3 | Prism, violet |
Z = 4 | 0.64 × 0.50 × 0.41 mm |
Data collection top
Stoe IPDS II diffractometer | 5762 independent reflections |
Radiation source: sealed X-ray tube, 12 x 0.4 mm long-fine focus | 5101 reflections with I > 2σ(I) |
Plane graphite monochromator | Rint = 0.031 |
Detector resolution: 6.67 pixels mm-1 | θmax = 28.3°, θmin = 2.3° |
ω scans | h = −23→23 |
Absorption correction: integration (X-RED32; Stoe & Cie, 2002) | k = −10→10 |
Tmin = 0.577, Tmax = 0.693 | l = −23→22 |
15539 measured reflections | |
Refinement top
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)] = 0.030 | H-atom parameters constrained |
wR(F2) = 0.073 | w = 1/[σ2(Fo2) + (0.0489P)2] where P = (Fo2 + 2Fc2)/3 |
S = 0.98 | (Δ/σ)max = 0.001 |
5762 reflections | Δρmax = 0.50 e Å−3 |
280 parameters | Δρmin = −0.32 e Å−3 |
1 restraint | Absolute structure: Flack (1983), with how many Friedel pairs |
Primary atom site location: structure-invariant direct methods | Absolute structure parameter: 0.000 (1) |
Special details top
Geometry. Bond distances, angles etc. have been calculated using the rounded
fractional coordinates. All su's are estimated from the variances of the
(full) variance-covariance matrix. The cell e.s.d.'s are taken into account in
the estimation of distances, angles and torsion angles |
Refinement. Refinement on F2 for ALL reflections except those flagged by the user
for potential systematic errors. Weighted R-factors wR and all
goodnesses of fit S are based on F2, conventional
R-factors R are based on F, with F set to zero for
negative F2. The observed criterion of F2 > 2σ(F2)
is used only for calculating -R-factor-obs 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 | |
Co1 | 0.43647 (1) | 0.13445 (3) | 0.99175 (2) | 0.0221 (1) | |
Cl1 | 0.52384 (3) | 0.29074 (7) | 1.05419 (3) | 0.0294 (1) | |
Cl2 | 0.41752 (3) | −0.14960 (7) | 1.02076 (4) | 0.0351 (2) | |
O1 | 0.30541 (10) | 0.0041 (2) | 0.70782 (10) | 0.0323 (5) | |
O2 | 0.25378 (14) | 0.5134 (3) | 1.20599 (12) | 0.0515 (7) | |
N1 | 0.45752 (11) | 0.1537 (2) | 0.88137 (11) | 0.0259 (5) | |
N2 | 0.45672 (11) | 0.0868 (3) | 0.76074 (11) | 0.0273 (5) | |
N3 | 0.33842 (9) | 0.2607 (2) | 1.01024 (10) | 0.0257 (5) | |
N4 | 0.25644 (10) | 0.4643 (2) | 1.04593 (12) | 0.0281 (5) | |
C1 | 0.44138 (13) | 0.0342 (3) | 0.83076 (13) | 0.0270 (6) | |
C2 | 0.48519 (13) | 0.2969 (3) | 0.84154 (12) | 0.0253 (6) | |
C3 | 0.51056 (15) | 0.4610 (3) | 0.86561 (14) | 0.0326 (7) | |
C4 | 0.53533 (17) | 0.5767 (3) | 0.81145 (15) | 0.0385 (8) | |
C5 | 0.53532 (16) | 0.5326 (3) | 0.73497 (15) | 0.0359 (8) | |
C6 | 0.50993 (14) | 0.3725 (3) | 0.71034 (14) | 0.0324 (7) | |
C7 | 0.48500 (12) | 0.2557 (3) | 0.76531 (13) | 0.0263 (6) | |
C8 | 0.43941 (15) | −0.0083 (3) | 0.69226 (14) | 0.0340 (7) | |
C9 | 0.36518 (14) | 0.0502 (3) | 0.65847 (13) | 0.0324 (7) | |
C10 | 0.23301 (14) | 0.0545 (3) | 0.67792 (15) | 0.0353 (7) | |
C11 | 0.17177 (17) | −0.0089 (4) | 0.7295 (2) | 0.0501 (10) | |
C12 | 0.32948 (12) | 0.4122 (3) | 1.04334 (13) | 0.0261 (6) | |
C13 | 0.26592 (10) | 0.2065 (3) | 0.98884 (14) | 0.0244 (5) | |
C14 | 0.24169 (13) | 0.0546 (3) | 0.95324 (13) | 0.0307 (7) | |
C15 | 0.16422 (14) | 0.0370 (3) | 0.94086 (14) | 0.0329 (7) | |
C16 | 0.11307 (14) | 0.1664 (3) | 0.96345 (15) | 0.0339 (7) | |
C17 | 0.13585 (12) | 0.3169 (3) | 0.99857 (15) | 0.0313 (6) | |
C18 | 0.21374 (12) | 0.3344 (3) | 1.01154 (12) | 0.0259 (6) | |
C19 | 0.22826 (15) | 0.6201 (3) | 1.08385 (17) | 0.0378 (8) | |
C20 | 0.19570 (15) | 0.5781 (4) | 1.16058 (19) | 0.0440 (9) | |
C21 | 0.2321 (3) | 0.4574 (6) | 1.2803 (2) | 0.0707 (14) | |
C22 | 0.2174 (5) | 0.5930 (7) | 1.3331 (3) | 0.117 (3) | |
H1 | 0.42140 | −0.07550 | 0.84230 | 0.0320* | |
H3 | 0.51080 | 0.49120 | 0.91600 | 0.0390* | |
H4 | 0.55250 | 0.68690 | 0.82590 | 0.0460* | |
H5 | 0.55290 | 0.61390 | 0.70030 | 0.0430* | |
H6 | 0.50940 | 0.34330 | 0.65990 | 0.0390* | |
H8A | 0.43690 | −0.13280 | 0.70300 | 0.0410* | |
H8B | 0.48000 | 0.01020 | 0.65640 | 0.0410* | |
H9A | 0.36570 | 0.17620 | 0.65080 | 0.0390* | |
H9B | 0.35770 | −0.00620 | 0.61040 | 0.0390* | |
H10A | 0.22620 | 0.00340 | 0.62870 | 0.0420* | |
H10B | 0.23040 | 0.18110 | 0.67320 | 0.0420* | |
H11A | 0.12300 | 0.02360 | 0.70990 | 0.0750* | |
H11B | 0.17850 | 0.04330 | 0.77790 | 0.0750* | |
H11C | 0.17460 | −0.13430 | 0.73390 | 0.0750* | |
H12 | 0.36950 | 0.47720 | 1.06310 | 0.0310* | |
H14 | 0.27590 | −0.03150 | 0.93830 | 0.0370* | |
H15 | 0.14600 | −0.06300 | 0.91710 | 0.0390* | |
H16 | 0.06150 | 0.14970 | 0.95430 | 0.0410* | |
H17 | 0.10130 | 0.40280 | 1.01300 | 0.0380* | |
H19A | 0.18910 | 0.67440 | 1.05350 | 0.0450* | |
H19B | 0.26950 | 0.70370 | 1.08930 | 0.0450* | |
H20A | 0.17420 | 0.68320 | 1.18270 | 0.0530* | |
H20B | 0.15560 | 0.49130 | 1.15600 | 0.0530* | |
H21A | 0.18680 | 0.38540 | 1.27610 | 0.0850* | |
H21B | 0.27230 | 0.38360 | 1.29990 | 0.0850* | |
H22A | 0.20430 | 0.54170 | 1.38040 | 0.1760* | |
H22B | 0.17600 | 0.66420 | 1.31580 | 0.1760* | |
H22C | 0.26200 | 0.66430 | 1.33890 | 0.1760* | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
Co1 | 0.0199 (1) | 0.0253 (1) | 0.0211 (1) | −0.0004 (1) | 0.0013 (1) | 0.0011 (1) |
Cl1 | 0.0283 (2) | 0.0343 (3) | 0.0256 (2) | −0.0066 (2) | −0.0049 (2) | 0.0032 (2) |
Cl2 | 0.0312 (3) | 0.0274 (3) | 0.0468 (3) | −0.0012 (2) | 0.0050 (2) | 0.0084 (2) |
O1 | 0.0375 (9) | 0.0339 (9) | 0.0255 (9) | −0.0002 (7) | −0.0013 (7) | 0.0025 (7) |
O2 | 0.0601 (13) | 0.0547 (13) | 0.0396 (11) | 0.0020 (10) | 0.0091 (10) | −0.0080 (9) |
N1 | 0.0281 (9) | 0.0281 (9) | 0.0214 (9) | −0.0022 (7) | 0.0015 (7) | −0.0003 (7) |
N2 | 0.0310 (9) | 0.0272 (9) | 0.0238 (10) | −0.0024 (7) | 0.0020 (8) | −0.0054 (7) |
N3 | 0.0204 (8) | 0.0290 (8) | 0.0276 (11) | 0.0017 (6) | −0.0004 (7) | 0.0003 (7) |
N4 | 0.0249 (8) | 0.0259 (9) | 0.0335 (10) | 0.0032 (7) | 0.0015 (8) | 0.0011 (8) |
C1 | 0.0304 (10) | 0.0258 (10) | 0.0249 (11) | −0.0036 (8) | 0.0033 (9) | −0.0021 (8) |
C2 | 0.0277 (10) | 0.0282 (10) | 0.0200 (10) | −0.0018 (8) | −0.0001 (8) | −0.0013 (9) |
C3 | 0.0406 (13) | 0.0341 (12) | 0.0230 (12) | −0.0066 (10) | −0.0020 (10) | −0.0012 (9) |
C4 | 0.0516 (15) | 0.0350 (13) | 0.0289 (13) | −0.0135 (11) | −0.0045 (12) | 0.0010 (10) |
C5 | 0.0450 (14) | 0.0359 (13) | 0.0269 (12) | −0.0097 (11) | −0.0003 (11) | 0.0056 (10) |
C6 | 0.0357 (12) | 0.0395 (13) | 0.0219 (11) | −0.0028 (10) | 0.0006 (9) | 0.0025 (10) |
C7 | 0.0254 (10) | 0.0299 (11) | 0.0236 (11) | −0.0002 (8) | 0.0008 (9) | −0.0018 (8) |
C8 | 0.0407 (13) | 0.0366 (13) | 0.0248 (12) | −0.0039 (10) | 0.0014 (10) | −0.0085 (9) |
C9 | 0.0447 (13) | 0.0304 (11) | 0.0222 (11) | −0.0059 (10) | −0.0001 (10) | −0.0018 (9) |
C10 | 0.0406 (13) | 0.0310 (11) | 0.0344 (13) | 0.0018 (10) | −0.0080 (11) | −0.0028 (10) |
C11 | 0.0420 (16) | 0.063 (2) | 0.0453 (17) | −0.0029 (13) | −0.0034 (13) | 0.0025 (14) |
C12 | 0.0210 (9) | 0.0268 (10) | 0.0304 (12) | −0.0022 (7) | −0.0007 (8) | 0.0011 (8) |
C13 | 0.0208 (8) | 0.0308 (9) | 0.0217 (9) | 0.0004 (7) | 0.0018 (10) | 0.0032 (10) |
C14 | 0.0257 (11) | 0.0374 (12) | 0.0291 (13) | 0.0000 (9) | −0.0001 (9) | −0.0029 (10) |
C15 | 0.0309 (12) | 0.0396 (12) | 0.0281 (12) | −0.0073 (10) | −0.0040 (10) | −0.0013 (10) |
C16 | 0.0247 (10) | 0.0437 (13) | 0.0334 (12) | −0.0024 (9) | −0.0049 (9) | 0.0081 (10) |
C17 | 0.0233 (9) | 0.0394 (11) | 0.0313 (12) | 0.0063 (8) | 0.0006 (10) | 0.0073 (11) |
C18 | 0.0243 (9) | 0.0276 (10) | 0.0259 (12) | 0.0014 (8) | −0.0006 (8) | 0.0053 (7) |
C19 | 0.0340 (12) | 0.0242 (11) | 0.0551 (16) | 0.0060 (9) | 0.0026 (11) | −0.0012 (11) |
C20 | 0.0383 (13) | 0.0314 (13) | 0.0624 (19) | −0.0006 (10) | 0.0173 (13) | −0.0144 (12) |
C21 | 0.092 (3) | 0.068 (2) | 0.052 (2) | −0.012 (2) | 0.011 (2) | −0.0042 (17) |
C22 | 0.214 (8) | 0.085 (4) | 0.053 (3) | 0.014 (4) | 0.030 (4) | −0.004 (2) |
Geometric parameters (Å, º) top
Co1—Cl1 | 2.2423 (6) | C17—C18 | 1.396 (3) |
Co1—Cl2 | 2.2516 (6) | C19—C20 | 1.521 (4) |
Co1—N1 | 2.014 (2) | C21—C22 | 1.424 (7) |
Co1—N3 | 2.0021 (16) | C1—H1 | 0.9303 |
O1—C9 | 1.417 (3) | C3—H3 | 0.9304 |
O1—C10 | 1.433 (3) | C4—H4 | 0.9294 |
O2—C20 | 1.395 (4) | C5—H5 | 0.9297 |
O2—C21 | 1.447 (4) | C6—H6 | 0.9294 |
N1—C1 | 1.315 (3) | C8—H8A | 0.9694 |
N1—C2 | 1.392 (3) | C8—H8B | 0.9700 |
N2—C1 | 1.343 (3) | C9—H9A | 0.9704 |
N2—C7 | 1.383 (3) | C9—H9B | 0.9704 |
N2—C8 | 1.456 (3) | C10—H10A | 0.9703 |
N3—C12 | 1.307 (3) | C10—H10B | 0.9699 |
N3—C13 | 1.394 (2) | C11—H11A | 0.9590 |
N4—C12 | 1.345 (3) | C11—H11B | 0.9602 |
N4—C18 | 1.387 (3) | C11—H11C | 0.9605 |
N4—C19 | 1.455 (3) | C12—H12 | 0.9304 |
C2—C3 | 1.396 (3) | C14—H14 | 0.9296 |
C2—C7 | 1.399 (3) | C15—H15 | 0.9298 |
C3—C4 | 1.381 (4) | C16—H16 | 0.9302 |
C4—C5 | 1.409 (4) | C17—H17 | 0.9298 |
C5—C6 | 1.372 (3) | C19—H19A | 0.9697 |
C6—C7 | 1.397 (3) | C19—H19B | 0.9703 |
C8—C9 | 1.506 (4) | C20—H20A | 0.9703 |
C10—C11 | 1.498 (4) | C20—H20B | 0.9705 |
C13—C14 | 1.389 (3) | C21—H21A | 0.9703 |
C13—C18 | 1.399 (3) | C21—H21B | 0.9691 |
C14—C15 | 1.387 (3) | C22—H22A | 0.9602 |
C15—C16 | 1.395 (3) | C22—H22B | 0.9594 |
C16—C17 | 1.368 (3) | C22—H22C | 0.9598 |
| | | |
Co1···C16i | 3.894 (2) | C18···H20B | 3.0256 |
Co1···H3 | 3.3078 | C19···H17 | 3.0553 |
Co1···H14 | 3.2383 | C20···H22B | 2.8742 |
Co1···H16i | 3.1583 | C21···H10Bvii | 2.9227 |
Cl1···N1 | 3.466 (2) | C22···H20A | 2.8790 |
Cl1···N3 | 3.3617 (17) | H1···H8A | 2.5446 |
Cl1···C3 | 3.622 (3) | H3···Co1 | 3.3078 |
Cl1···C12 | 3.546 (2) | H3···Cl1 | 2.9154 |
Cl1···C8ii | 3.340 (3) | H3···C17iii | 3.0261 |
Cl2···C16i | 3.591 (3) | H3···H17iii | 2.4893 |
Cl2···N1 | 3.4726 (19) | H4···C16iii | 2.9052 |
Cl2···N3 | 3.4284 (17) | H5···Cl1xiii | 3.0301 |
Cl1···H8Aii | 3.0022 | H6···C8 | 3.0057 |
Cl1···H8Bii | 2.9345 | H6···H8B | 2.5922 |
Cl1···H3 | 2.9154 | H8A···H1 | 2.5446 |
Cl1···H19Aiii | 2.9181 | H8A···Cl1viii | 3.0022 |
Cl1···H12 | 3.0678 | H8A···H20Avi | 2.4323 |
Cl1···H5iv | 3.0301 | H8B···C6 | 2.9727 |
Cl1···H17iii | 2.8029 | H8B···H6 | 2.5922 |
Cl2···H14 | 3.0312 | H8B···Cl1viii | 2.9345 |
Cl2···H19Bv | 3.0869 | H9A···C7 | 2.9941 |
Cl2···H12v | 3.0629 | H9A···H10B | 2.4129 |
Cl2···H16i | 2.7970 | H9A···C17ix | 2.9270 |
O1···N2 | 2.894 (3) | H9A···H20Bix | 2.4330 |
O1···C1 | 3.257 (3) | H9B···H10A | 2.3365 |
O1···C20vi | 3.356 (3) | H9B···C15ix | 3.0750 |
O2···N4 | 2.888 (3) | H9B···C16ix | 2.9843 |
O2···C12 | 3.291 (3) | H10A···H9B | 2.3365 |
O1···H20Avi | 2.5130 | H10A···C13ix | 2.9456 |
O2···H10Bvii | 2.6152 | H10A···H19Bvi | 2.3922 |
N1···Cl1 | 3.466 (2) | H10B···H9A | 2.4129 |
N1···Cl2 | 3.4726 (19) | H10B···O2ix | 2.6152 |
N1···N3 | 3.220 (3) | H10B···C12ix | 3.0999 |
N2···O1 | 2.894 (3) | H10B···C21ix | 2.9227 |
N3···Cl1 | 3.3617 (17) | H11B···C15 | 2.9264 |
N3···Cl2 | 3.4284 (17) | H12···Cl1 | 3.0678 |
N3···N1 | 3.220 (3) | H12···Cl2xiv | 3.0629 |
N4···O2 | 2.888 (3) | H12···H19B | 2.5086 |
C1···O1 | 3.257 (3) | H14···Co1 | 3.2383 |
C3···Cl1 | 3.622 (3) | H14···Cl2 | 3.0312 |
C8···Cl1viii | 3.340 (3) | H16···Co1x | 3.1583 |
C9···C17ix | 3.510 (3) | H16···Cl2x | 2.7970 |
C10···C13ix | 3.576 (4) | H17···C19 | 3.0553 |
C12···O2 | 3.291 (3) | H17···Cl1xii | 2.8029 |
C13···C10vii | 3.576 (4) | H17···H3xii | 2.4893 |
C16···Cl2x | 3.591 (3) | H19A···C17 | 3.0447 |
C16···Co1x | 3.894 (2) | H19A···Cl1xii | 2.9181 |
C17···C9vii | 3.510 (3) | H19B···Cl2xiv | 3.0869 |
C20···O1xi | 3.356 (3) | H19B···H12 | 2.5086 |
C6···H8B | 2.9727 | H19B···H10Axi | 2.3922 |
C7···H9A | 2.9941 | H20A···C22 | 2.8790 |
C8···H6 | 3.0057 | H20A···H22B | 2.3857 |
C8···H20Avi | 3.0905 | H20A···O1xi | 2.5130 |
C9···H20Avi | 2.9147 | H20A···C8xi | 3.0905 |
C12···H10Bvii | 3.0999 | H20A···C9xi | 2.9147 |
C13···H10Avii | 2.9456 | H20A···H8Axi | 2.4323 |
C15···H9Bvii | 3.0750 | H20B···C18 | 3.0256 |
C15···H11B | 2.9264 | H20B···H21A | 2.3598 |
C16···H9Bvii | 2.9843 | H20B···H9Avii | 2.4330 |
C16···H4xii | 2.9052 | H21A···H20B | 2.3598 |
C17···H9Avii | 2.9270 | H22B···C20 | 2.8742 |
C17···H3xii | 3.0261 | H22B···H20A | 2.3857 |
C17···H19A | 3.0447 | | |
| | | |
Cl1—Co1—Cl2 | 119.84 (2) | C6—C5—H5 | 119.14 |
Cl1—Co1—N1 | 108.89 (5) | C5—C6—H6 | 121.87 |
Cl1—Co1—N3 | 104.61 (5) | C7—C6—H6 | 121.84 |
Cl2—Co1—N1 | 108.86 (5) | N2—C8—H8A | 109.29 |
Cl2—Co1—N3 | 107.27 (5) | N2—C8—H8B | 109.29 |
N1—Co1—N3 | 106.57 (7) | C9—C8—H8A | 109.27 |
C9—O1—C10 | 111.09 (18) | C9—C8—H8B | 109.22 |
C20—O2—C21 | 116.5 (3) | H8A—C8—H8B | 107.88 |
Co1—N1—C1 | 125.78 (15) | O1—C9—H9A | 109.92 |
Co1—N1—C2 | 128.56 (14) | O1—C9—H9B | 109.98 |
C1—N1—C2 | 105.45 (19) | C8—C9—H9A | 109.98 |
C1—N2—C7 | 107.2 (2) | C8—C9—H9B | 110.00 |
C1—N2—C8 | 126.5 (2) | H9A—C9—H9B | 108.34 |
C7—N2—C8 | 126.1 (2) | O1—C10—H10A | 109.92 |
Co1—N3—C12 | 127.09 (14) | O1—C10—H10B | 109.95 |
Co1—N3—C13 | 126.85 (14) | C11—C10—H10A | 109.92 |
C12—N3—C13 | 106.04 (17) | C11—C10—H10B | 109.91 |
C12—N4—C18 | 106.91 (17) | H10A—C10—H10B | 108.34 |
C12—N4—C19 | 125.62 (19) | C10—C11—H11A | 109.52 |
C18—N4—C19 | 127.26 (19) | C10—C11—H11B | 109.45 |
N1—C1—N2 | 113.1 (2) | C10—C11—H11C | 109.53 |
N1—C2—C3 | 131.1 (2) | H11A—C11—H11B | 109.44 |
N1—C2—C7 | 108.79 (19) | H11A—C11—H11C | 109.48 |
C3—C2—C7 | 120.2 (2) | H11B—C11—H11C | 109.40 |
C2—C3—C4 | 117.2 (2) | N3—C12—H12 | 123.48 |
C3—C4—C5 | 121.9 (2) | N4—C12—H12 | 123.49 |
C4—C5—C6 | 121.6 (2) | C13—C14—H14 | 121.48 |
C5—C6—C7 | 116.3 (2) | C15—C14—H14 | 121.43 |
N2—C7—C2 | 105.5 (2) | C14—C15—H15 | 119.40 |
N2—C7—C6 | 131.7 (2) | C16—C15—H15 | 119.35 |
C2—C7—C6 | 122.8 (2) | C15—C16—H16 | 118.74 |
N2—C8—C9 | 111.8 (2) | C17—C16—H16 | 118.75 |
O1—C9—C8 | 108.63 (19) | C16—C17—H17 | 121.79 |
O1—C10—C11 | 108.8 (2) | C18—C17—H17 | 121.85 |
N3—C12—N4 | 113.03 (19) | N4—C19—H19A | 109.23 |
N3—C13—C14 | 130.84 (19) | N4—C19—H19B | 109.18 |
N3—C13—C18 | 108.27 (19) | C20—C19—H19A | 109.13 |
C14—C13—C18 | 120.87 (18) | C20—C19—H19B | 109.20 |
C13—C14—C15 | 117.1 (2) | H19A—C19—H19B | 107.85 |
C14—C15—C16 | 121.3 (2) | O2—C20—H20A | 109.86 |
C15—C16—C17 | 122.5 (2) | O2—C20—H20B | 109.88 |
C16—C17—C18 | 116.4 (2) | C19—C20—H20A | 109.93 |
N4—C18—C13 | 105.75 (18) | C19—C20—H20B | 109.92 |
N4—C18—C17 | 132.3 (2) | H20A—C20—H20B | 108.32 |
C13—C18—C17 | 121.9 (2) | O2—C21—H21A | 108.18 |
N4—C19—C20 | 112.2 (2) | O2—C21—H21B | 108.15 |
O2—C20—C19 | 108.9 (2) | C22—C21—H21A | 108.24 |
O2—C21—C22 | 116.3 (4) | C22—C21—H21B | 108.29 |
N1—C1—H1 | 123.46 | H21A—C21—H21B | 107.36 |
N2—C1—H1 | 123.46 | C21—C22—H22A | 109.42 |
C2—C3—H3 | 121.46 | C21—C22—H22B | 109.54 |
C4—C3—H3 | 121.36 | C21—C22—H22C | 109.54 |
C3—C4—H4 | 119.00 | H22A—C22—H22B | 109.43 |
C5—C4—H4 | 119.07 | H22A—C22—H22C | 109.35 |
C4—C5—H5 | 119.26 | H22B—C22—H22C | 109.54 |
| | | |
Cl1—Co1—N1—C1 | 150.71 (18) | Co1—N3—C13—C14 | 2.8 (4) |
Cl2—Co1—N1—C1 | 18.5 (2) | Co1—N3—C12—N4 | 178.71 (15) |
N3—Co1—N1—C1 | −96.95 (19) | C12—N4—C18—C13 | −0.4 (2) |
Cl1—Co1—N1—C2 | −35.4 (2) | C18—N4—C19—C20 | 75.7 (3) |
Cl2—Co1—N1—C2 | −167.65 (17) | C19—N4—C12—N3 | 175.2 (2) |
N3—Co1—N1—C2 | 77.0 (2) | C19—N4—C18—C13 | −175.3 (2) |
Cl1—Co1—N3—C12 | 7.77 (19) | C18—N4—C12—N3 | 0.2 (3) |
Cl2—Co1—N3—C12 | 136.05 (18) | C19—N4—C18—C17 | 4.6 (4) |
N1—Co1—N3—C12 | −107.48 (19) | C12—N4—C19—C20 | −98.3 (3) |
Cl1—Co1—N3—C13 | −173.82 (17) | C12—N4—C18—C17 | 179.5 (3) |
Cl2—Co1—N3—C13 | −45.54 (19) | C7—C2—C3—C4 | −0.5 (4) |
N1—Co1—N3—C13 | 70.93 (19) | N1—C2—C3—C4 | 179.7 (2) |
C10—O1—C9—C8 | −179.15 (18) | N1—C2—C7—N2 | 0.2 (2) |
C9—O1—C10—C11 | 175.9 (2) | C3—C2—C7—N2 | −179.7 (2) |
C21—O2—C20—C19 | −176.8 (3) | N1—C2—C7—C6 | −179.7 (2) |
C20—O2—C21—C22 | −75.5 (6) | C3—C2—C7—C6 | 0.4 (4) |
Co1—N1—C2—C7 | −175.23 (15) | C2—C3—C4—C5 | 0.0 (4) |
C1—N1—C2—C3 | 179.5 (3) | C3—C4—C5—C6 | 0.6 (4) |
C2—N1—C1—N2 | 0.4 (3) | C4—C5—C6—C7 | −0.7 (4) |
C1—N1—C2—C7 | −0.4 (2) | C5—C6—C7—N2 | −179.7 (2) |
Co1—N1—C1—N2 | 175.50 (15) | C5—C6—C7—C2 | 0.2 (4) |
Co1—N1—C2—C3 | 4.6 (4) | N2—C8—C9—O1 | −65.5 (2) |
C1—N2—C7—C6 | 180.0 (2) | N3—C13—C18—C17 | −179.5 (2) |
C8—N2—C7—C2 | 174.2 (2) | C14—C13—C18—N4 | 178.8 (2) |
C1—N2—C7—C2 | 0.1 (2) | C18—C13—C14—C15 | 0.6 (3) |
C7—N2—C1—N1 | −0.4 (3) | C14—C13—C18—C17 | −1.0 (4) |
C8—N2—C1—N1 | −174.4 (2) | N3—C13—C14—C15 | 178.6 (2) |
C7—N2—C8—C9 | −77.8 (3) | N3—C13—C18—N4 | 0.4 (3) |
C1—N2—C8—C9 | 95.2 (3) | C13—C14—C15—C16 | −0.2 (4) |
C8—N2—C7—C6 | −6.0 (4) | C14—C15—C16—C17 | 0.2 (4) |
C12—N3—C13—C18 | −0.3 (3) | C15—C16—C17—C18 | −0.6 (4) |
Co1—N3—C13—C18 | −178.95 (15) | C16—C17—C18—N4 | −178.8 (2) |
C13—N3—C12—N4 | 0.0 (3) | C16—C17—C18—C13 | 1.0 (4) |
C12—N3—C13—C14 | −178.5 (3) | N4—C19—C20—O2 | 63.7 (3) |
Symmetry codes: (i) x+1/2, −y, z; (ii) −x+1, −y, z+1/2; (iii) x+1/2, −y+1, z; (iv) −x+1, −y+1, z+1/2; (v) x, y−1, z; (vi) −x+1/2, y−1, z−1/2; (vii) −x+1/2, y, z+1/2; (viii) −x+1, −y, z−1/2; (ix) −x+1/2, y, z−1/2; (x) x−1/2, −y, z; (xi) −x+1/2, y+1, z+1/2; (xii) x−1/2, −y+1, z; (xiii) −x+1, −y+1, z−1/2; (xiv) x, y+1, z. |
Hydrogen-bond geometry (Å, º) top
D—H···A | D—H | H···A | D···A | D—H···A |
C16—H16···Cl2x | 0.93 | 2.80 | 3.591 (3) | 144 |
C17—H17···Cl1xii | 0.93 | 2.80 | 3.717 (2) | 168 |
C20—H20A···O1xi | 0.97 | 2.51 | 3.356 (3) | 145 |
Symmetry codes: (x) x−1/2, −y, z; (xi) −x+1/2, y+1, z+1/2; (xii) x−1/2, −y+1, z. |