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In the title compound, [CoCl(C
24H
21N
7)]
2[CoCl
4]·4CH
3OH, the crystal packing is stabilized by O—H
Cl, N—H
Cl and N—H
O hydrogen bonds, weak C—H
Cl interactions, and π–π stacking. The anion lies on a twofold rotation axis.
Supporting information
CCDC reference: 274407
Key indicators
- Single-crystal X-ray study
- T = 298 K
- Mean (C-C) = 0.018 Å
- R factor = 0.092
- wR factor = 0.259
- Data-to-parameter ratio = 15.3
checkCIF/PLATON results
No syntax errors found
Alert level B
PLAT241_ALERT_2_B Check High Ueq as Compared to Neighbors for C22
PLAT341_ALERT_3_B Low Bond Precision on C-C bonds (x 1000) Ang ... 18
Alert level C
RFACR01_ALERT_3_C The value of the weighted R factor is > 0.25
Weighted R factor given 0.259
PLAT026_ALERT_3_C Ratio Observed / Unique Reflections too Low .... 40 Perc.
PLAT042_ALERT_1_C Calc. and Rep. MoietyFormula Strings Differ .... ?
PLAT084_ALERT_2_C High R2 Value .................................. 0.26
PLAT220_ALERT_2_C Large Non-Solvent C Ueq(max)/Ueq(min) ... 3.02 Ratio
PLAT242_ALERT_2_C Check Low Ueq as Compared to Neighbors for C2
PLAT244_ALERT_4_C Low 'Solvent' Ueq as Compared to Neighbors for Co2
PLAT250_ALERT_2_C Large U3/U1 Ratio for Average U(i,j) Tensor .... 2.04
PLAT480_ALERT_4_C Long H...A H-Bond Reported H16 .. CL1 .. 2.85 Ang.
PLAT480_ALERT_4_C Long H...A H-Bond Reported H16 .. C16 .. 2.90 Ang.
PLAT601_ALERT_2_C Structure Contains Solvent Accessible VOIDS of . 49.00 A 3
0 ALERT level A = In general: serious problem
2 ALERT level B = Potentially serious problem
11 ALERT level C = Check and explain
0 ALERT level G = General alerts; check
1 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
6 ALERT type 2 Indicator that the structure model may be wrong or deficient
3 ALERT type 3 Indicator that the structure quality may be low
3 ALERT type 4 Improvement, methodology, query or suggestion
Data collection: SMART (Bruker, 2000); cell refinement: SAINT (Bruker, 2000); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: SHELXTL/PC (Sheldrick, 1999); software used to prepare material for publication: SHELXTL/PC.
Bis{chloro[tris(1
H-benzimidazol-2-ylmethyl)amine]cobalt(II)}
tetrachlorocobalt(II) methanol tetrasolvate
top
Crystal data top
[CoCl(C24H21N7)]2[CoCl4]·4CH4O | F(000) = 2732 |
Mr = 1332.61 | Dx = 1.402 Mg m−3 |
Monoclinic, C2/c | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: -C 2yc | Cell parameters from 1380 reflections |
a = 23.432 (7) Å | θ = 2.7–16.1° |
b = 16.752 (5) Å | µ = 1.09 mm−1 |
c = 16.134 (5) Å | T = 298 K |
β = 94.372 (5)° | Block, black |
V = 6315 (3) Å3 | 0.30 × 0.20 × 0.10 mm |
Z = 4 | |
Data collection top
Bruker SMART 1K CCD area-detector diffractometer | 5539 independent reflections |
Radiation source: fine-focus sealed tube | 2235 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.085 |
ω scans | θmax = 25.0°, θmin = 1.5° |
Absorption correction: multi-scan (SADABS; Sheldrick, 2000) | h = −27→24 |
Tmin = 0.737, Tmax = 0.899 | k = −14→19 |
15114 measured reflections | l = −19→18 |
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)] = 0.092 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.259 | H-atom parameters constrained |
S = 0.94 | w = 1/[σ2(Fo2) + (0.1169P)2] where P = (Fo2 + 2Fc2)/3 |
5539 reflections | (Δ/σ)max = 0.002 |
361 parameters | Δρmax = 0.70 e Å−3 |
6 restraints | Δρmin = −0.64 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 | |
Co1 | 0.09552 (5) | 0.31455 (8) | 0.38875 (7) | 0.0626 (5) | |
Cl1 | 0.13355 (11) | 0.40684 (18) | 0.30595 (17) | 0.0977 (10) | |
N1 | 0.0612 (3) | 0.2136 (5) | 0.4755 (4) | 0.066 (2) | |
N2 | 0.1573 (3) | 0.3009 (5) | 0.4850 (4) | 0.063 (2) | |
N3 | 0.1940 (4) | 0.2464 (6) | 0.6001 (5) | 0.080 (2) | |
H3 | 0.1990 | 0.2125 | 0.6400 | 0.096* | |
N4 | 0.0225 (3) | 0.3610 (5) | 0.4270 (4) | 0.063 (2) | |
N5 | −0.0538 (3) | 0.3597 (5) | 0.4986 (5) | 0.074 (2) | |
H5 | −0.0776 | 0.3436 | 0.5331 | 0.089* | |
N6 | 0.0829 (3) | 0.2197 (6) | 0.3126 (5) | 0.069 (2) | |
N7 | 0.0641 (4) | 0.0889 (6) | 0.2933 (6) | 0.096 (3) | |
H7 | 0.0532 | 0.0411 | 0.3037 | 0.116* | |
C1 | 0.1101 (4) | 0.1807 (6) | 0.5248 (6) | 0.076 (3) | |
H1A | 0.0986 | 0.1619 | 0.5779 | 0.091* | |
H1B | 0.1259 | 0.1360 | 0.4959 | 0.091* | |
C2 | 0.1528 (4) | 0.2433 (6) | 0.5377 (5) | 0.057 (2) | |
C3 | 0.2030 (4) | 0.3486 (6) | 0.5168 (6) | 0.066 (3) | |
C4 | 0.2262 (5) | 0.3122 (8) | 0.5895 (6) | 0.079 (3) | |
C5 | 0.2729 (5) | 0.3460 (9) | 0.6369 (8) | 0.103 (4) | |
H5A | 0.2886 | 0.3218 | 0.6852 | 0.124* | |
C6 | 0.2934 (5) | 0.4136 (11) | 0.6098 (9) | 0.112 (5) | |
H6 | 0.3239 | 0.4371 | 0.6411 | 0.134* | |
C7 | 0.2724 (5) | 0.4521 (8) | 0.5373 (10) | 0.112 (5) | |
H7A | 0.2891 | 0.4994 | 0.5213 | 0.135* | |
C8 | 0.2266 (4) | 0.4200 (7) | 0.4892 (7) | 0.084 (3) | |
H8 | 0.2120 | 0.4448 | 0.4405 | 0.101* | |
C9 | 0.0194 (4) | 0.2523 (6) | 0.5275 (5) | 0.069 (3) | |
H9A | 0.0384 | 0.2683 | 0.5805 | 0.083* | |
H9B | −0.0109 | 0.2151 | 0.5380 | 0.083* | |
C10 | −0.0049 (4) | 0.3237 (6) | 0.4822 (6) | 0.064 (2) | |
C11 | −0.0108 (4) | 0.4266 (6) | 0.4055 (6) | 0.063 (3) | |
C12 | −0.0586 (4) | 0.4266 (6) | 0.4506 (6) | 0.069 (3) | |
C13 | −0.1007 (5) | 0.4861 (7) | 0.4409 (7) | 0.091 (3) | |
H13 | −0.1339 | 0.4838 | 0.4691 | 0.109* | |
C14 | −0.0909 (5) | 0.5474 (7) | 0.3883 (7) | 0.090 (3) | |
H14 | −0.1173 | 0.5887 | 0.3816 | 0.108* | |
C15 | −0.0426 (5) | 0.5495 (7) | 0.3451 (6) | 0.093 (3) | |
H15 | −0.0371 | 0.5920 | 0.3094 | 0.112* | |
C16 | −0.0025 (4) | 0.4900 (7) | 0.3537 (6) | 0.081 (3) | |
H16 | 0.0302 | 0.4925 | 0.3246 | 0.097* | |
C17 | 0.0334 (4) | 0.1539 (7) | 0.4207 (6) | 0.086 (3) | |
H17A | −0.0070 | 0.1662 | 0.4105 | 0.103* | |
H17B | 0.0369 | 0.1015 | 0.4463 | 0.103* | |
C18 | 0.0614 (4) | 0.1543 (8) | 0.3412 (7) | 0.085 (3) | |
C19 | 0.0999 (4) | 0.1966 (9) | 0.2356 (7) | 0.083 (3) | |
C20 | 0.0890 (5) | 0.1170 (11) | 0.2227 (8) | 0.098 (4) | |
C21 | 0.1019 (6) | 0.0718 (12) | 0.1496 (10) | 0.140 (7) | |
H21 | 0.0945 | 0.0175 | 0.1427 | 0.167* | |
C22 | 0.1259 (8) | 0.1175 (16) | 0.0931 (12) | 0.171 (11) | |
H22 | 0.1357 | 0.0925 | 0.0447 | 0.206* | |
C23 | 0.1374 (6) | 0.1990 (13) | 0.1003 (9) | 0.138 (7) | |
H23 | 0.1533 | 0.2259 | 0.0572 | 0.166* | |
C24 | 0.1247 (4) | 0.2418 (9) | 0.1749 (7) | 0.104 (4) | |
H24 | 0.1326 | 0.2959 | 0.1820 | 0.125* | |
C25 | 0.2215 (8) | 0.1046 (11) | 0.7871 (11) | 0.210 (8) | |
H25A | 0.2373 | 0.1289 | 0.8376 | 0.315* | |
H25B | 0.2341 | 0.0501 | 0.7849 | 0.315* | |
H25C | 0.1805 | 0.1060 | 0.7855 | 0.315* | |
O1 | 0.2399 (4) | 0.1464 (8) | 0.7189 (6) | 0.161 (4) | |
H1 | 0.2749 | 0.1479 | 0.7220 | 0.242* | |
C26 | 0.8202 (10) | 0.3701 (10) | 0.6502 (13) | 0.249 (10) | |
H26A | 0.8176 | 0.3566 | 0.7076 | 0.374* | |
H26B | 0.7830 | 0.3656 | 0.6210 | 0.374* | |
H26C | 0.8338 | 0.4239 | 0.6461 | 0.374* | |
O2 | 0.8674 (6) | 0.3052 (7) | 0.6065 (6) | 0.180 (4) | |
H2 | 0.8805 | 0.2737 | 0.6420 | 0.271* | |
Co2 | 1.0000 | 0.85514 (13) | 0.2500 | 0.1017 (8) | |
Cl2 | 1.0145 (3) | 0.9309 (2) | 0.36469 (19) | 0.222 (3) | |
Cl3 | 0.9242 (2) | 0.7777 (4) | 0.2594 (2) | 0.231 (3) | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
Co1 | 0.0507 (7) | 0.0807 (10) | 0.0567 (7) | 0.0113 (7) | 0.0050 (5) | 0.0071 (7) |
Cl1 | 0.0819 (18) | 0.118 (2) | 0.0956 (19) | 0.0102 (17) | 0.0233 (15) | 0.0363 (18) |
N1 | 0.065 (5) | 0.067 (5) | 0.064 (5) | 0.015 (4) | 0.001 (4) | −0.004 (4) |
N2 | 0.044 (4) | 0.076 (6) | 0.068 (5) | 0.001 (4) | 0.003 (4) | −0.005 (5) |
N3 | 0.066 (6) | 0.103 (8) | 0.073 (6) | 0.030 (5) | 0.013 (5) | 0.006 (5) |
N4 | 0.053 (5) | 0.073 (6) | 0.062 (5) | 0.018 (4) | 0.002 (4) | −0.005 (4) |
N5 | 0.059 (5) | 0.088 (6) | 0.077 (5) | 0.016 (5) | 0.017 (4) | −0.004 (5) |
N6 | 0.058 (5) | 0.090 (7) | 0.062 (5) | −0.004 (5) | 0.017 (4) | −0.017 (5) |
N7 | 0.091 (7) | 0.092 (8) | 0.102 (7) | 0.013 (5) | −0.021 (6) | −0.026 (7) |
C1 | 0.078 (7) | 0.071 (7) | 0.080 (7) | 0.011 (6) | 0.014 (5) | 0.018 (6) |
C2 | 0.056 (6) | 0.065 (7) | 0.049 (5) | 0.020 (5) | 0.003 (5) | 0.002 (5) |
C3 | 0.056 (6) | 0.065 (7) | 0.077 (7) | 0.019 (6) | 0.008 (5) | −0.020 (6) |
C4 | 0.066 (7) | 0.106 (10) | 0.065 (7) | 0.039 (7) | 0.008 (6) | −0.010 (7) |
C5 | 0.055 (8) | 0.163 (14) | 0.088 (8) | 0.038 (8) | −0.008 (7) | −0.024 (10) |
C6 | 0.062 (9) | 0.164 (16) | 0.107 (11) | 0.009 (9) | −0.008 (7) | −0.039 (11) |
C7 | 0.056 (8) | 0.096 (10) | 0.189 (14) | −0.010 (7) | 0.037 (9) | −0.053 (11) |
C8 | 0.054 (7) | 0.096 (9) | 0.105 (8) | 0.012 (6) | 0.013 (6) | −0.015 (8) |
C9 | 0.070 (6) | 0.072 (7) | 0.067 (6) | 0.004 (5) | 0.015 (5) | 0.005 (6) |
C10 | 0.061 (6) | 0.061 (7) | 0.070 (6) | 0.006 (6) | 0.014 (5) | −0.003 (6) |
C11 | 0.056 (6) | 0.077 (8) | 0.055 (6) | 0.015 (6) | −0.002 (5) | −0.011 (6) |
C12 | 0.078 (7) | 0.067 (8) | 0.062 (6) | 0.013 (6) | −0.003 (5) | −0.011 (6) |
C13 | 0.085 (8) | 0.097 (9) | 0.091 (8) | 0.026 (7) | 0.002 (6) | −0.022 (8) |
C14 | 0.107 (9) | 0.085 (9) | 0.077 (7) | 0.043 (7) | 0.000 (7) | 0.001 (7) |
C15 | 0.106 (9) | 0.110 (10) | 0.064 (7) | 0.030 (8) | 0.009 (6) | 0.002 (7) |
C16 | 0.089 (8) | 0.090 (8) | 0.064 (6) | 0.038 (7) | 0.006 (5) | 0.014 (6) |
C17 | 0.079 (7) | 0.097 (9) | 0.084 (7) | 0.005 (6) | 0.022 (6) | 0.005 (7) |
C18 | 0.064 (7) | 0.097 (10) | 0.092 (9) | 0.012 (7) | −0.021 (6) | −0.039 (8) |
C19 | 0.059 (7) | 0.119 (11) | 0.073 (8) | 0.008 (7) | 0.006 (6) | −0.003 (8) |
C20 | 0.060 (7) | 0.154 (14) | 0.078 (9) | 0.022 (8) | 0.000 (6) | −0.024 (10) |
C21 | 0.101 (11) | 0.194 (19) | 0.118 (12) | 0.046 (11) | −0.025 (9) | −0.074 (14) |
C22 | 0.132 (16) | 0.27 (3) | 0.112 (14) | 0.10 (2) | −0.001 (11) | −0.06 (2) |
C23 | 0.100 (10) | 0.24 (2) | 0.073 (9) | 0.075 (14) | 0.023 (7) | 0.009 (13) |
C24 | 0.069 (7) | 0.161 (13) | 0.081 (8) | 0.032 (8) | −0.008 (6) | −0.017 (9) |
C25 | 0.200 (11) | 0.217 (11) | 0.217 (11) | 0.005 (9) | 0.045 (9) | 0.044 (9) |
O1 | 0.111 (6) | 0.246 (11) | 0.131 (7) | 0.074 (8) | 0.040 (6) | 0.091 (8) |
C26 | 0.32 (3) | 0.155 (17) | 0.28 (2) | 0.056 (18) | 0.06 (2) | 0.052 (18) |
O2 | 0.195 (11) | 0.209 (13) | 0.148 (8) | 0.008 (9) | 0.088 (8) | 0.041 (8) |
Co2 | 0.155 (2) | 0.0885 (17) | 0.0637 (12) | 0.000 | 0.0255 (13) | 0.000 |
Cl2 | 0.514 (9) | 0.084 (3) | 0.065 (2) | −0.016 (4) | 0.006 (3) | −0.0075 (19) |
Cl3 | 0.173 (4) | 0.418 (8) | 0.099 (3) | −0.111 (5) | −0.005 (3) | 0.019 (4) |
Geometric parameters (Å, º) top
Co1—N6 | 2.016 (8) | C9—H9B | 0.9700 |
Co1—N4 | 2.019 (7) | C11—C16 | 1.374 (12) |
Co1—N2 | 2.053 (7) | C11—C12 | 1.381 (11) |
Co1—Cl1 | 2.269 (3) | C12—C13 | 1.402 (13) |
Co1—N1 | 2.375 (7) | C13—C14 | 1.363 (13) |
N1—C1 | 1.453 (10) | C13—H13 | 0.9300 |
N1—C17 | 1.456 (11) | C14—C15 | 1.374 (13) |
N1—C9 | 1.485 (10) | C14—H14 | 0.9300 |
N2—C2 | 1.296 (10) | C15—C16 | 1.369 (13) |
N2—C3 | 1.402 (11) | C15—H15 | 0.9300 |
N3—C2 | 1.342 (11) | C16—H16 | 0.9300 |
N3—C4 | 1.353 (12) | C17—C18 | 1.485 (14) |
N3—H3 | 0.8600 | C17—H17A | 0.9700 |
N4—C10 | 1.297 (10) | C17—H17B | 0.9700 |
N4—C11 | 1.378 (11) | C19—C20 | 1.370 (15) |
N5—C10 | 1.337 (10) | C19—C24 | 1.399 (14) |
N5—C12 | 1.363 (11) | C20—C21 | 1.453 (17) |
N5—H5 | 0.8600 | C21—C22 | 1.35 (2) |
N6—C18 | 1.305 (13) | C21—H21 | 0.9300 |
N6—C19 | 1.389 (12) | C22—C23 | 1.39 (2) |
N7—C18 | 1.345 (12) | C22—H22 | 0.9300 |
N7—C20 | 1.400 (13) | C23—C24 | 1.452 (17) |
N7—H7 | 0.8600 | C23—H23 | 0.9300 |
C1—C2 | 1.452 (12) | C24—H24 | 0.9300 |
C1—H1A | 0.9700 | C25—O1 | 1.400 (16) |
C1—H1B | 0.9700 | C25—H25A | 0.9600 |
C3—C4 | 1.395 (13) | C25—H25B | 0.9600 |
C3—C8 | 1.405 (13) | C25—H25C | 0.9600 |
C4—C5 | 1.406 (16) | O1—H1 | 0.8200 |
C5—C6 | 1.318 (16) | C26—O2 | 1.739 (19) |
C5—H5A | 0.9300 | C26—H26A | 0.9600 |
C6—C7 | 1.392 (17) | C26—H26B | 0.9600 |
C6—H6 | 0.9300 | C26—H26C | 0.9600 |
C7—C8 | 1.384 (14) | O2—H2 | 0.8200 |
C7—H7A | 0.9300 | Co2—Cl3i | 2.214 (5) |
C8—H8 | 0.9300 | Co2—Cl3 | 2.214 (5) |
C9—C10 | 1.493 (12) | Co2—Cl2 | 2.248 (3) |
C9—H9A | 0.9700 | Co2—Cl2i | 2.248 (3) |
| | | |
N6—Co1—N4 | 113.7 (3) | N4—C10—C9 | 122.0 (8) |
N6—Co1—N2 | 115.8 (3) | N5—C10—C9 | 124.4 (9) |
N4—Co1—N2 | 112.2 (3) | C16—C11—N4 | 131.7 (9) |
N6—Co1—Cl1 | 102.9 (3) | C16—C11—C12 | 118.6 (10) |
N4—Co1—Cl1 | 107.3 (3) | N4—C11—C12 | 109.5 (9) |
N2—Co1—Cl1 | 103.6 (2) | N5—C12—C11 | 105.3 (9) |
N6—Co1—N1 | 76.0 (3) | N5—C12—C13 | 132.5 (11) |
N4—Co1—N1 | 76.2 (3) | C11—C12—C13 | 122.2 (11) |
N2—Co1—N1 | 74.1 (3) | C14—C13—C12 | 117.0 (11) |
Cl1—Co1—N1 | 176.44 (19) | C14—C13—H13 | 121.5 |
C1—N1—C17 | 111.7 (8) | C12—C13—H13 | 121.5 |
C1—N1—C9 | 112.6 (7) | C13—C14—C15 | 121.4 (10) |
C17—N1—C9 | 111.0 (7) | C13—C14—H14 | 119.3 |
C1—N1—Co1 | 107.7 (6) | C15—C14—H14 | 119.3 |
C17—N1—Co1 | 106.7 (5) | C16—C15—C14 | 120.9 (11) |
C9—N1—Co1 | 106.8 (5) | C16—C15—H15 | 119.5 |
C2—N2—C3 | 106.4 (8) | C14—C15—H15 | 119.5 |
C2—N2—Co1 | 119.4 (6) | C15—C16—C11 | 119.8 (10) |
C3—N2—Co1 | 133.5 (7) | C15—C16—H16 | 120.1 |
C2—N3—C4 | 108.3 (9) | C11—C16—H16 | 120.1 |
C2—N3—H3 | 125.8 | N1—C17—C18 | 108.3 (9) |
C4—N3—H3 | 125.8 | N1—C17—H17A | 110.0 |
C10—N4—C11 | 104.8 (8) | C18—C17—H17A | 110.0 |
C10—N4—Co1 | 120.0 (7) | N1—C17—H17B | 110.0 |
C11—N4—Co1 | 135.1 (7) | C18—C17—H17B | 110.0 |
C10—N5—C12 | 107.1 (8) | H17A—C17—H17B | 108.4 |
C10—N5—H5 | 126.5 | N6—C18—N7 | 116.4 (11) |
C12—N5—H5 | 126.5 | N6—C18—C17 | 121.2 (11) |
C18—N6—C19 | 103.1 (10) | N7—C18—C17 | 122.4 (13) |
C18—N6—Co1 | 119.3 (7) | C20—C19—N6 | 110.1 (11) |
C19—N6—Co1 | 136.6 (9) | C20—C19—C24 | 120.3 (12) |
C18—N7—C20 | 103.6 (11) | N6—C19—C24 | 129.6 (13) |
C18—N7—H7 | 128.2 | C19—C20—N7 | 106.7 (11) |
C20—N7—H7 | 128.2 | C19—C20—C21 | 125.6 (15) |
C2—C1—N1 | 108.1 (8) | N7—C20—C21 | 127.7 (17) |
C2—C1—H1A | 110.1 | C22—C21—C20 | 112 (2) |
N1—C1—H1A | 110.1 | C22—C21—H21 | 123.9 |
C2—C1—H1B | 110.1 | C20—C21—H21 | 123.9 |
N1—C1—H1B | 110.1 | C21—C22—C23 | 126 (2) |
H1A—C1—H1B | 108.4 | C21—C22—H22 | 117.0 |
N2—C2—N3 | 111.9 (9) | C23—C22—H22 | 117.0 |
N2—C2—C1 | 122.2 (8) | C22—C23—C24 | 120.2 (18) |
N3—C2—C1 | 125.7 (10) | C22—C23—H23 | 119.9 |
C4—C3—N2 | 107.2 (10) | C24—C23—H23 | 119.9 |
C4—C3—C8 | 120.1 (11) | C19—C24—C23 | 115.8 (14) |
N2—C3—C8 | 132.7 (10) | C19—C24—H24 | 122.1 |
N3—C4—C3 | 106.1 (10) | C23—C24—H24 | 122.1 |
N3—C4—C5 | 132.7 (12) | O1—C25—H25A | 109.5 |
C3—C4—C5 | 121.2 (13) | O1—C25—H25B | 109.5 |
C6—C5—C4 | 117.1 (14) | H25A—C25—H25B | 109.5 |
C6—C5—H5A | 121.5 | O1—C25—H25C | 109.5 |
C4—C5—H5A | 121.5 | H25A—C25—H25C | 109.5 |
C5—C6—C7 | 124.1 (14) | H25B—C25—H25C | 109.5 |
C5—C6—H6 | 117.9 | C25—O1—H1 | 109.5 |
C7—C6—H6 | 117.9 | O2—C26—H26A | 109.5 |
C8—C7—C6 | 120.1 (13) | O2—C26—H26B | 109.5 |
C8—C7—H7A | 120.0 | H26A—C26—H26B | 109.5 |
C6—C7—H7A | 120.0 | O2—C26—H26C | 109.5 |
C7—C8—C3 | 117.4 (11) | H26A—C26—H26C | 109.5 |
C7—C8—H8 | 121.3 | H26B—C26—H26C | 109.5 |
C3—C8—H8 | 121.3 | C26—O2—H2 | 109.5 |
N1—C9—C10 | 108.5 (7) | Cl3i—Co2—Cl3 | 108.2 (4) |
N1—C9—H9A | 110.0 | Cl3i—Co2—Cl2 | 108.4 (2) |
C10—C9—H9A | 110.0 | Cl3—Co2—Cl2 | 110.27 (19) |
N1—C9—H9B | 110.0 | Cl3i—Co2—Cl2i | 110.27 (19) |
C10—C9—H9B | 110.0 | Cl3—Co2—Cl2i | 108.4 (2) |
H9A—C9—H9B | 108.4 | Cl2—Co2—Cl2i | 111.3 (2) |
N4—C10—N5 | 113.3 (9) | | |
| | | |
N6—Co1—N1—C1 | 101.3 (6) | C4—C3—C8—C7 | −0.8 (13) |
N4—Co1—N1—C1 | −139.5 (6) | N2—C3—C8—C7 | 179.3 (9) |
N2—Co1—N1—C1 | −21.2 (6) | C1—N1—C9—C10 | 143.8 (8) |
N6—Co1—N1—C17 | −18.8 (6) | C17—N1—C9—C10 | −90.1 (9) |
N4—Co1—N1—C17 | 100.4 (6) | Co1—N1—C9—C10 | 25.8 (8) |
N2—Co1—N1—C17 | −141.3 (6) | C11—N4—C10—N5 | 0.1 (10) |
N6—Co1—N1—C9 | −137.6 (6) | Co1—N4—C10—N5 | −177.2 (6) |
N4—Co1—N1—C9 | −18.4 (5) | C11—N4—C10—C9 | −174.5 (8) |
N2—Co1—N1—C9 | 99.9 (6) | Co1—N4—C10—C9 | 8.2 (11) |
N6—Co1—N2—C2 | −58.0 (7) | C12—N5—C10—N4 | −0.5 (10) |
N4—Co1—N2—C2 | 74.7 (7) | C12—N5—C10—C9 | 174.0 (8) |
Cl1—Co1—N2—C2 | −169.9 (6) | N1—C9—C10—N4 | −25.1 (12) |
N1—Co1—N2—C2 | 7.3 (6) | N1—C9—C10—N5 | 161.0 (8) |
N6—Co1—N2—C3 | 133.0 (7) | C10—N4—C11—C16 | 176.0 (10) |
N4—Co1—N2—C3 | −94.4 (8) | Co1—N4—C11—C16 | −7.4 (15) |
Cl1—Co1—N2—C3 | 21.1 (8) | C10—N4—C11—C12 | 0.3 (9) |
N1—Co1—N2—C3 | −161.7 (8) | Co1—N4—C11—C12 | 177.0 (6) |
N6—Co1—N4—C10 | 74.0 (7) | C10—N5—C12—C11 | 0.6 (9) |
N2—Co1—N4—C10 | −59.7 (7) | C10—N5—C12—C13 | 179.1 (10) |
Cl1—Co1—N4—C10 | −172.9 (6) | C16—C11—C12—N5 | −176.9 (8) |
N1—Co1—N4—C10 | 6.3 (6) | N4—C11—C12—N5 | −0.6 (10) |
N6—Co1—N4—C11 | −102.3 (8) | C16—C11—C12—C13 | 4.5 (14) |
N2—Co1—N4—C11 | 124.0 (8) | N4—C11—C12—C13 | −179.2 (8) |
Cl1—Co1—N4—C11 | 10.8 (8) | N5—C12—C13—C14 | 177.8 (10) |
N1—Co1—N4—C11 | −169.9 (8) | C11—C12—C13—C14 | −3.9 (14) |
N4—Co1—N6—C18 | −64.9 (8) | C12—C13—C14—C15 | 1.8 (16) |
N2—Co1—N6—C18 | 67.1 (8) | C13—C14—C15—C16 | −0.3 (17) |
Cl1—Co1—N6—C18 | 179.4 (7) | C14—C15—C16—C11 | 0.8 (15) |
N1—Co1—N6—C18 | 2.9 (7) | N4—C11—C16—C15 | −178.1 (9) |
N4—Co1—N6—C19 | 129.1 (9) | C12—C11—C16—C15 | −2.8 (14) |
N2—Co1—N6—C19 | −98.9 (10) | C1—N1—C17—C18 | −88.4 (10) |
Cl1—Co1—N6—C19 | 13.4 (10) | C9—N1—C17—C18 | 145.1 (8) |
N1—Co1—N6—C19 | −163.2 (10) | Co1—N1—C17—C18 | 29.1 (9) |
C17—N1—C1—C2 | 146.9 (8) | C19—N6—C18—N7 | 2.6 (11) |
C9—N1—C1—C2 | −87.4 (9) | Co1—N6—C18—N7 | −167.7 (6) |
Co1—N1—C1—C2 | 30.0 (8) | C19—N6—C18—C17 | −174.9 (8) |
C3—N2—C2—N3 | −3.3 (9) | Co1—N6—C18—C17 | 14.9 (12) |
Co1—N2—C2—N3 | −175.1 (5) | C20—N7—C18—N6 | −2.4 (11) |
C3—N2—C2—C1 | −179.0 (8) | C20—N7—C18—C17 | 175.0 (9) |
Co1—N2—C2—C1 | 9.2 (11) | N1—C17—C18—N6 | −31.6 (13) |
C4—N3—C2—N2 | 2.6 (10) | N1—C17—C18—N7 | 151.1 (8) |
C4—N3—C2—C1 | 178.1 (8) | C18—N6—C19—C20 | −1.6 (11) |
N1—C1—C2—N2 | −28.6 (11) | Co1—N6—C19—C20 | 165.9 (8) |
N1—C1—C2—N3 | 156.3 (8) | C18—N6—C19—C24 | 178.3 (10) |
C2—N2—C3—C4 | 2.8 (9) | Co1—N6—C19—C24 | −14.1 (17) |
Co1—N2—C3—C4 | 172.9 (6) | N6—C19—C20—N7 | 0.3 (12) |
C2—N2—C3—C8 | −177.4 (9) | C24—C19—C20—N7 | −179.7 (8) |
Co1—N2—C3—C8 | −7.3 (14) | N6—C19—C20—C21 | −178.9 (10) |
C2—N3—C4—C3 | −0.7 (10) | C24—C19—C20—C21 | 1.1 (17) |
C2—N3—C4—C5 | 177.3 (10) | C18—N7—C20—C19 | 1.2 (11) |
N2—C3—C4—N3 | −1.2 (9) | C18—N7—C20—C21 | −179.7 (11) |
C8—C3—C4—N3 | 178.9 (8) | C19—C20—C21—C22 | −1 (2) |
N2—C3—C4—C5 | −179.6 (8) | N7—C20—C21—C22 | −179.9 (13) |
C8—C3—C4—C5 | 0.6 (13) | C20—C21—C22—C23 | −1 (3) |
N3—C4—C5—C6 | −177.4 (11) | C21—C22—C23—C24 | 2 (3) |
C3—C4—C5—C6 | 0.4 (16) | C20—C19—C24—C23 | 0.0 (15) |
C4—C5—C6—C7 | −1 (2) | N6—C19—C24—C23 | −180.0 (10) |
C5—C6—C7—C8 | 1 (2) | C22—C23—C24—C19 | −1.3 (19) |
C6—C7—C8—C3 | 0.2 (15) | | |
Symmetry code: (i) −x+2, y, −z+1/2. |
Hydrogen-bond geometry (Å, º) top
D—H···A | D—H | H···A | D···A | D—H···A |
O1—H1···Cl1ii | 0.82 | 2.41 | 3.152 (8) | 152 |
N7—H7···Cl2iii | 0.86 | 2.31 | 3.145 (11) | 163 |
N5—H5···O2iv | 0.86 | 1.93 | 2.786 (12) | 178 |
N3—H3···O1 | 0.86 | 1.89 | 2.706 (12) | 158 |
C8—H8···Cl1 | 0.93 | 2.81 | 3.545 (12) | 137 |
C16—H16···Cl1 | 0.93 | 2.85 | 3.616 (10) | 140 |
C24—H24···Cl1 | 0.93 | 2.73 | 3.477 (13) | 138 |
C16—H16···C16v | 0.93 | 2.90 | 3.357 (18) | 112 |
Symmetry codes: (ii) −x+1/2, −y+1/2, −z+1; (iii) x−1, y−1, z; (iv) x−1, y, z; (v) −x, y, −z+1/2. |
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