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The structure of {3-[(4-fluoro­phenyl)­methyl]-1H-benzim­id­azol-2-yl­idene}{1-[2-(4-methoxy­phenyl)­ethyl]-4-piperidin-1-io}­ammonium tetra­chloro­cobaltate(II), (C28H33FN4O)[CoCl4], is isomorphous with its CuCl42− analogue. It contains diprotonated cations of astemizole hydrogen-bonded to three Cl atoms in two different CoCl42− anions, with Cl...N distances in the range 3.109 (5)–3.212 (5) Å. One of the Cl atoms in the CoCl42− anion is disordered and the geometry around cobalt is distorted tetrahedral. The phenyl­ethyl C atoms of the (4-methoxy­phenyl)­ethyl group attached to the piperidine ring are disordered, indicating the presence of two conformers in the crystal.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536804007743/lh6193sup1.cif
Contains datablocks global, I

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536804007743/lh6193Isup2.hkl
Contains datablock I

CCDC reference: 239049

Key indicators

  • Single-crystal X-ray study
  • T = 170 K
  • Mean [sigma](C-C) = 0.009 Å
  • Disorder in solvent or counterion
  • R factor = 0.065
  • wR factor = 0.157
  • Data-to-parameter ratio = 14.3

checkCIF/PLATON results

No syntax errors found



Alert level A PLAT432_ALERT_2_A Short Inter X...Y Contact C21' .. C21' .. 2.86 Ang.
Author Response: The phenylethyl C-atoms of the (4-methoxyphenyl)ethyl group attched to the piperdin ring are disordered over sites (C20-C27) and (C20'-C27') which is likely the cause of this contact.

Alert level B PLAT432_ALERT_2_B Short Inter X...Y Contact C21' .. C22' .. 2.95 Ang.
Author Response: The phenylethyl C-atoms of the (4-methoxyphenyl)ethyl group attched to the piperdin ring are disordered over sites (C20-C27) and (C20'-C27') which is likely the cause of this contact.

Alert level C PLAT165_ALERT_3_C Nr. of Status R Flagged Non-Hydrogen Atoms ..... 12 PLAT213_ALERT_2_C Atom C24 has ADP max/min Ratio ............. 3.30 prolat PLAT213_ALERT_2_C Atom C26 has ADP max/min Ratio ............. 3.10 prolat PLAT213_ALERT_2_C Atom C24' has ADP max/min Ratio ............. 3.30 prolat PLAT213_ALERT_2_C Atom C26' has ADP max/min Ratio ............. 3.10 prolat PLAT241_ALERT_2_C Check High U(eq) as Compared to Neighbors .... O1 PLAT244_ALERT_4_C Low Solvent U(eq) as Compared to Neighbors .... Co1 PLAT301_ALERT_3_C Main Residue Disorder ......................... 19.00 Perc. PLAT302_ALERT_4_C Anion/Solvent Disorder ......................... 17.00 Perc. PLAT341_ALERT_3_C Low Bond Precision on C-C bonds (x 1000) Ang ... 9 PLAT411_ALERT_2_C Short Inter H...H Contact H19B .. H26' .. 2.14 Ang. PLAT432_ALERT_2_C Short Inter X...Y Contact Cl4 .. C24' .. 3.18 Ang.
Author Response: The phenylethyl C-atoms of the (4-methoxyphenyl)ethyl group attched to the piperdin ring are disordered over sites (C20-C27) and (C20'-C27') which is likely the cause of this contact.
PLAT432_ALERT_2_C Short Inter X...Y Contact  C21'   ..  C23'    ..       3.13 Ang.
Author Response: The phenylethyl C-atoms of the (4-methoxyphenyl)ethyl group attched to the piperdin ring are disordered over sites (C20-C27) and (C20'-C27') which is likely the cause of this contact.

1 ALERT level A = In general: serious problem 1 ALERT level B = Potentially serious problem 13 ALERT level C = Check and explain 0 ALERT level G = General alerts; check 0 ALERT type 1 CIF construction/syntax error, inconsistent or missing data 10 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 2 ALERT type 4 Improvement, methodology, query or suggestion

Computing details top

Data collection: COLLECT (Hooft, 1998); cell refinement: HKL DENZO (Otwinowski & Minor, 1997); data reduction: SCALEPACK (Otwinowski & Minor, 1997); program(s) used to solve structure: SAPI91 (Fan, 1991); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEPII (Johnson, 1976); software used to prepare material for publication: SHELXL97.

{3-[(4-fluorophenyl)methyl]-1H-benzimidazol-2-ylidene}{1-[2-(4- methoxyphenyl)ethyl]-4-piperidin-1-io}ammonium tetrachlorocobaltate(II) top
Crystal data top
(C28H33FN4O)[CoCl4]F(000) = 1364
Mr = 661.31Dx = 1.465 Mg m3
Monoclinic, P21/nMo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ynCell parameters from 9625 reflections
a = 9.327 (3) Åθ = 2.5–25.0°
b = 15.836 (6) ŵ = 0.96 mm1
c = 20.691 (9) ÅT = 170 K
β = 101.186 (14)°Prism, blue
V = 2998 (2) Å30.10 × 0.08 × 0.06 mm
Z = 4
Data collection top
Nonius KappaCCD
diffractometer
5205 independent reflections
Radiation source: fine-focus sealed tube2899 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.084
ω and φ scansθmax = 25.0°, θmin = 2.5°
Absorption correction: multi-scan
(SORTAV; Blessing, 1997)
h = 1111
Tmin = 0.91, Tmax = 0.94k = 1718
9625 measured reflectionsl = 2424
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)] = 0.065Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.157H-atom parameters constrained
S = 1.02 w = 1/[σ2(Fo2) + (0.062P)2 + 2.13P]
where P = (Fo2 + 2Fc2)/3
5205 reflections(Δ/σ)max < 0.001
363 parametersΔρmax = 0.44 e Å3
4 restraintsΔρmin = 0.55 e Å3
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/UeqOcc. (<1)
Co10.79619 (8)0.01356 (4)0.23763 (3)0.0316 (2)
Cl10.936 (3)0.1012 (10)0.2373 (3)0.055 (4)0.65 (6)
Cl1'0.874 (4)0.1199 (14)0.2414 (10)0.054 (4)0.35 (6)
Cl20.9301 (2)0.13013 (10)0.22853 (8)0.0655 (5)
Cl30.61643 (15)0.01524 (9)0.14424 (6)0.0462 (4)
Cl40.71713 (17)0.02805 (13)0.33399 (7)0.0652 (5)
F10.5850 (5)0.4120 (3)0.0490 (2)0.1018 (15)
O10.6535 (4)0.1665 (3)0.73968 (16)0.0538 (11)
N10.2122 (5)0.1057 (3)0.0308 (2)0.0362 (11)
N20.0640 (5)0.1242 (3)0.0998 (2)0.0362 (11)
H20.03230.13170.13680.043*
N30.3185 (5)0.1169 (3)0.1442 (2)0.0376 (11)
H30.40500.10580.13520.045*
N40.4391 (6)0.1258 (3)0.35295 (18)0.0452 (13)
H40.51900.09170.35020.054*
C10.2036 (7)0.1153 (3)0.0950 (3)0.0346 (13)
C20.0241 (6)0.1196 (3)0.0371 (2)0.0336 (13)
C30.1726 (7)0.1222 (3)0.0171 (3)0.0437 (15)
H3A0.23570.13060.04750.052*
C40.2267 (7)0.1117 (4)0.0501 (3)0.0475 (16)
H4A0.32930.11240.06620.057*
C50.1320 (7)0.1003 (3)0.0943 (3)0.0419 (15)
H50.17160.09480.14000.050*
C60.0173 (7)0.0968 (3)0.0731 (3)0.0378 (14)
H60.08100.08760.10310.045*
C70.0705 (6)0.1070 (3)0.0066 (2)0.0339 (13)
C80.3475 (6)0.0993 (4)0.0043 (3)0.0425 (15)
H8A0.32740.06590.03690.051*
H8B0.42210.06870.03630.051*
C90.4075 (6)0.1838 (4)0.0096 (3)0.0416 (15)
C100.4951 (7)0.2303 (4)0.0396 (3)0.0532 (17)
H100.51540.20850.08320.064*
C110.5539 (7)0.3077 (5)0.0270 (4)0.0654 (19)
H110.61300.33930.06110.079*
C120.5234 (8)0.3368 (5)0.0367 (4)0.066 (2)
C130.4395 (7)0.2944 (5)0.0870 (4)0.065 (2)
H130.42060.31660.13050.078*
C140.3828 (7)0.2182 (4)0.0729 (3)0.0505 (16)
H140.32410.18760.10770.061*
C150.3104 (7)0.1360 (3)0.2124 (2)0.0385 (14)
H150.22240.17190.21290.046*
C160.2993 (7)0.0561 (3)0.2526 (2)0.0425 (15)
H16A0.20710.02620.23450.051*
H16B0.38170.01790.24950.051*
C170.3031 (7)0.0790 (4)0.3243 (3)0.0478 (16)
H17A0.21710.11430.32740.057*
H17B0.29740.02680.35000.057*
C180.4498 (8)0.2058 (3)0.3146 (3)0.0552 (18)
H18A0.36710.24350.31820.066*
H18B0.54180.23560.33330.066*
C190.4468 (7)0.1855 (3)0.2432 (3)0.0473 (16)
H19A0.53460.15210.23960.057*
H19B0.45010.23870.21840.057*
C200.425 (3)0.1320 (15)0.4246 (5)0.040 (4)0.508 (4)
H20A0.34720.17240.42940.048*0.508 (4)
H20B0.40070.07620.44090.048*0.508 (4)
C210.5706 (12)0.1621 (7)0.4637 (5)0.038 (2)0.508 (4)
H21A0.58540.22160.45170.046*0.508 (4)
H21B0.64960.12820.45080.046*0.508 (4)
C220.5844 (9)0.1566 (5)0.5378 (3)0.035 (2)0.508 (4)
C230.4698 (8)0.1752 (5)0.5695 (3)0.0317 (19)0.508 (4)
H230.37650.18960.54440.038*0.508 (4)
C240.4917 (11)0.1727 (6)0.6378 (4)0.040 (3)0.508 (4)
H240.41340.18540.65950.049*0.508 (4)
C250.6282 (14)0.1517 (8)0.6745 (3)0.0271 (18)0.508 (4)
C260.7428 (10)0.1331 (9)0.6428 (5)0.031 (3)0.508 (4)
H260.83610.11870.66780.037*0.508 (4)
C270.7209 (8)0.1356 (7)0.5744 (5)0.0456 (19)0.508 (4)
H270.79930.12290.55270.055*0.508 (4)
C20'0.478 (3)0.1546 (16)0.4236 (5)0.040 (4)0.492 (4)
H20C0.39640.18670.43560.048*0.492 (4)
H20D0.56540.19170.42980.048*0.492 (4)
C21'0.5100 (13)0.0778 (7)0.4659 (5)0.038 (2)0.492 (4)
H21C0.59260.04620.45390.046*0.492 (4)
H21D0.42330.04040.45880.046*0.492 (4)
C22'0.5497 (9)0.1054 (5)0.5406 (3)0.035 (2)0.492 (4)
C23'0.4369 (7)0.1080 (5)0.5758 (3)0.0317 (19)0.492 (4)
H23'0.34100.09150.55520.038*0.492 (4)
C24'0.4646 (12)0.1347 (6)0.6410 (3)0.040 (3)0.492 (4)
H24'0.38750.13650.66500.049*0.492 (4)
C25'0.6050 (14)0.1588 (8)0.6711 (3)0.0271 (18)0.492 (4)
C26'0.7177 (10)0.1562 (9)0.6360 (5)0.031 (3)0.492 (4)
H26'0.81370.17270.65660.037*0.492 (4)
C27'0.6901 (8)0.1295 (7)0.5707 (5)0.0456 (19)0.492 (4)
H27'0.76710.12770.54670.055*0.492 (4)
C280.5393 (7)0.1650 (4)0.7760 (3)0.0501 (16)
H28A0.58010.17360.82280.075*
H28B0.48950.11020.76990.075*
H28C0.46910.21010.76030.075*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Co10.0312 (5)0.0337 (4)0.0303 (4)0.0020 (3)0.0071 (3)0.0014 (3)
Cl10.086 (10)0.041 (4)0.0395 (18)0.032 (5)0.014 (3)0.0037 (16)
Cl1'0.054 (9)0.049 (5)0.056 (4)0.012 (6)0.003 (5)0.001 (3)
Cl20.0880 (14)0.0670 (11)0.0481 (10)0.0386 (10)0.0297 (9)0.0149 (8)
Cl30.0395 (9)0.0659 (9)0.0312 (8)0.0039 (7)0.0022 (6)0.0031 (7)
Cl40.0413 (10)0.1254 (15)0.0326 (9)0.0078 (10)0.0163 (8)0.0039 (9)
F10.078 (3)0.113 (4)0.121 (4)0.024 (3)0.036 (3)0.044 (3)
O10.049 (3)0.076 (3)0.035 (3)0.005 (2)0.003 (2)0.015 (2)
N10.037 (3)0.045 (3)0.027 (3)0.011 (2)0.007 (2)0.006 (2)
N20.041 (3)0.042 (3)0.027 (3)0.008 (2)0.008 (2)0.002 (2)
N30.040 (3)0.047 (3)0.026 (3)0.002 (2)0.006 (2)0.003 (2)
N40.068 (4)0.037 (3)0.025 (3)0.018 (2)0.006 (2)0.005 (2)
C10.041 (4)0.034 (3)0.029 (3)0.006 (3)0.007 (3)0.009 (2)
C20.035 (4)0.035 (3)0.030 (3)0.013 (3)0.005 (3)0.004 (2)
C30.043 (4)0.054 (4)0.038 (4)0.016 (3)0.016 (3)0.010 (3)
C40.041 (4)0.054 (4)0.044 (4)0.008 (3)0.000 (3)0.008 (3)
C50.055 (5)0.043 (4)0.027 (3)0.008 (3)0.007 (3)0.004 (2)
C60.048 (4)0.039 (3)0.028 (3)0.008 (3)0.011 (3)0.003 (2)
C70.040 (4)0.032 (3)0.029 (3)0.008 (2)0.004 (3)0.000 (2)
C80.039 (4)0.062 (4)0.027 (3)0.018 (3)0.006 (3)0.010 (3)
C90.023 (3)0.068 (4)0.037 (4)0.015 (3)0.014 (3)0.008 (3)
C100.031 (4)0.085 (5)0.047 (4)0.005 (3)0.015 (3)0.022 (4)
C110.040 (4)0.096 (6)0.065 (5)0.009 (4)0.021 (4)0.008 (4)
C120.041 (5)0.085 (5)0.081 (6)0.002 (4)0.032 (4)0.030 (5)
C130.050 (5)0.091 (6)0.056 (5)0.017 (4)0.017 (4)0.027 (4)
C140.039 (4)0.072 (5)0.042 (4)0.020 (3)0.013 (3)0.011 (3)
C150.057 (4)0.028 (3)0.028 (3)0.001 (3)0.001 (3)0.001 (2)
C160.068 (5)0.027 (3)0.033 (3)0.001 (3)0.012 (3)0.004 (2)
C170.071 (5)0.044 (4)0.030 (3)0.013 (3)0.014 (3)0.006 (3)
C180.083 (5)0.024 (3)0.047 (4)0.008 (3)0.015 (3)0.007 (3)
C190.068 (5)0.031 (3)0.039 (4)0.000 (3)0.001 (3)0.004 (3)
C200.043 (16)0.032 (12)0.036 (4)0.003 (7)0.015 (5)0.020 (4)
C210.046 (6)0.044 (5)0.029 (5)0.001 (4)0.019 (4)0.004 (4)
C220.048 (6)0.028 (6)0.032 (4)0.000 (5)0.013 (4)0.012 (5)
C230.019 (4)0.044 (5)0.031 (4)0.004 (4)0.003 (4)0.001 (4)
C240.020 (6)0.070 (11)0.036 (4)0.016 (6)0.018 (4)0.002 (5)
C250.027 (5)0.023 (3)0.031 (3)0.001 (3)0.005 (3)0.007 (2)
C260.022 (5)0.010 (8)0.060 (5)0.007 (5)0.009 (4)0.002 (4)
C270.045 (5)0.048 (4)0.051 (4)0.006 (4)0.027 (4)0.002 (3)
C20'0.043 (16)0.032 (12)0.036 (4)0.003 (7)0.015 (5)0.020 (4)
C21'0.046 (6)0.044 (5)0.029 (5)0.001 (4)0.019 (4)0.004 (4)
C22'0.048 (6)0.028 (6)0.032 (4)0.000 (5)0.013 (4)0.012 (5)
C23'0.019 (4)0.044 (5)0.031 (4)0.004 (4)0.003 (4)0.001 (4)
C24'0.020 (6)0.070 (11)0.036 (4)0.016 (6)0.018 (4)0.002 (5)
C25'0.027 (5)0.023 (3)0.031 (3)0.001 (3)0.005 (3)0.007 (2)
C26'0.022 (5)0.010 (8)0.060 (5)0.007 (5)0.009 (4)0.002 (4)
C27'0.045 (5)0.048 (4)0.051 (4)0.006 (4)0.027 (4)0.002 (3)
C280.066 (5)0.060 (4)0.027 (3)0.010 (3)0.015 (3)0.004 (3)
Geometric parameters (Å, º) top
Co1—Cl1'2.232 (14)C15—C161.528 (7)
Co1—Cl12.240 (8)C15—H151.0000
Co1—Cl22.257 (2)C16—C171.521 (7)
Co1—Cl42.268 (2)C16—H16A0.9900
Co1—Cl32.300 (2)C16—H16B0.9900
F1—C121.367 (8)C17—H17A0.9900
O1—C251.344 (6)C17—H17B0.9900
O1—C25'1.409 (6)C18—C191.506 (8)
O1—C281.418 (7)C18—H18A0.9900
N1—C11.353 (6)C18—H18B0.9900
N1—C71.397 (7)C19—H19A0.9900
N1—C81.473 (7)C19—H19B0.9900
N2—C11.333 (7)C20—C211.51 (2)
N2—C21.397 (6)C20—H20A0.9900
N2—H20.8800C20—H20B0.9900
N3—C11.329 (6)C21—C221.516 (11)
N3—C151.459 (7)C21—H21A0.9900
N3—H30.8800C21—H21B0.9900
N4—C20'1.507 (8)C22—C231.3900
N4—C171.489 (7)C22—C271.3900
N4—C181.509 (7)C23—C241.3900
N4—C201.515 (8)C23—H230.9500
N4—H40.9300C24—C251.3900
C2—C31.367 (7)C24—H240.9500
C2—C71.395 (7)C25—C261.3900
C3—C41.395 (8)C26—C271.3900
C3—H3A0.9500C26—H260.9500
C4—C51.401 (8)C27—H270.9500
C4—H4A0.9500C20'—C21'1.49 (3)
C5—C61.377 (8)C20'—H20C0.9900
C5—H50.9500C20'—H20D0.9900
C6—C71.379 (7)C21'—C22'1.581 (12)
C6—H60.9500C21'—H21C0.9900
C8—C91.499 (8)C21'—H21D0.9900
C8—H8A0.9900C22'—C23'1.3900
C8—H8B0.9900C22'—C27'1.3900
C9—C101.387 (8)C23'—C24'1.3900
C9—C141.396 (8)C23'—H23'0.9500
C10—C111.389 (9)C24'—C25'1.3900
C10—H100.9500C24'—H24'0.9500
C11—C121.373 (9)C25'—C26'1.3900
C11—H110.9500C26'—C27'1.3900
C12—C131.353 (9)C26'—H26'0.9500
C13—C141.371 (9)C27'—H27'0.9500
C13—H130.9500C28—H28A0.9800
C14—H140.9500C28—H28B0.9800
C15—C191.524 (7)C28—H28C0.9800
Cl1'—Co1—Cl2126.6 (11)H16A—C16—H16B108.2
Cl1—Co1—Cl2109.3 (9)N4—C17—C16111.3 (5)
Cl1'—Co1—Cl4102.9 (9)N4—C17—H17A109.4
Cl1—Co1—Cl4112.0 (3)C16—C17—H17A109.4
Cl2—Co1—Cl4105.68 (7)N4—C17—H17B109.4
Cl1'—Co1—Cl3102.7 (4)C16—C17—H17B109.4
Cl1—Co1—Cl3109.7 (5)H17A—C17—H17B108.0
Cl2—Co1—Cl3104.21 (7)C19—C18—N4110.2 (4)
Cl4—Co1—Cl3115.42 (7)C19—C18—H18A109.6
C25—O1—C28121.6 (7)N4—C18—H18A109.6
C25'—O1—C28113.8 (7)C19—C18—H18B109.6
C1—N1—C7108.2 (4)N4—C18—H18B109.6
C1—N1—C8126.2 (5)H18A—C18—H18B108.1
C7—N1—C8125.5 (4)C18—C19—C15112.0 (5)
C1—N2—C2109.3 (4)C18—C19—H19A109.2
C1—N2—H2125.3C15—C19—H19A109.2
C2—N2—H2125.3C18—C19—H19B109.2
C1—N3—C15124.1 (5)C15—C19—H19B109.2
C1—N3—H3117.9H19A—C19—H19B107.9
C15—N3—H3117.9C21—C20—N4107.9 (11)
C20'—N4—C17124.4 (8)C21—C20—H20A110.1
C20'—N4—C18103.1 (9)N4—C20—H20A110.1
C17—N4—C18110.3 (4)C21—C20—H20B110.1
C17—N4—C20101.3 (7)N4—C20—H20B110.1
C18—N4—C20119.1 (10)H20A—C20—H20B108.4
C20'—N4—H4100.8C20—C21—C22114.5 (8)
C17—N4—H4108.6C20—C21—H21A108.6
C18—N4—H4108.6C22—C21—H21A108.6
C20—N4—H4108.6C20—C21—H21B108.6
N3—C1—N2126.5 (5)C22—C21—H21B108.6
N3—C1—N1124.2 (5)H21A—C21—H21B107.6
N2—C1—N1109.3 (5)C23—C22—C27120.0
C3—C2—C7122.7 (5)C23—C22—C21122.9 (7)
C3—C2—N2131.1 (5)C27—C22—C21117.1 (7)
C7—C2—N2106.2 (5)C24—C23—C22120.0
C2—C3—C4116.5 (5)C24—C23—H23120.0
C2—C3—H3A121.7C22—C23—H23120.0
C4—C3—H3A121.7C23—C24—C25120.0
C3—C4—C5121.0 (6)C23—C24—H24120.0
C3—C4—H4A119.5C25—C24—H24120.0
C5—C4—H4A119.5O1—C25—C26120.6 (9)
C6—C5—C4121.6 (5)O1—C25—C24118.0 (9)
C6—C5—H5119.2C26—C25—C24120.0
C4—C5—H5119.2C25—C26—C27120.0
C5—C6—C7117.3 (5)C25—C26—H26120.0
C5—C6—H6121.3C27—C26—H26120.0
C7—C6—H6121.3C26—C27—C22120.0
C6—C7—C2120.9 (5)C26—C27—H27120.0
C6—C7—N1132.1 (5)C22—C27—H27120.0
C2—C7—N1107.0 (4)N4—C20'—C21'107.7 (14)
N1—C8—C9112.9 (4)N4—C20'—H20C110.2
N1—C8—H8A109.0C21'—C20'—H20C110.2
C9—C8—H8A109.0N4—C20'—H20D110.2
N1—C8—H8B109.0C21'—C20'—H20D110.2
C9—C8—H8B109.0H20C—C20'—H20D108.5
H8A—C8—H8B107.8C20'—C21'—C22'109.3 (8)
C10—C9—C14116.6 (6)C20'—C21'—H21C109.8
C10—C9—C8121.4 (5)C22'—C21'—H21C109.8
C14—C9—C8122.0 (6)C20'—C21'—H21D109.8
C9—C10—C11121.9 (6)C22'—C21'—H21D109.8
C9—C10—H10119.1H21C—C21'—H21D108.3
C11—C10—H10119.1C23'—C22'—C27'120.0
C12—C11—C10117.5 (7)C23'—C22'—C21'117.5 (7)
C12—C11—H11121.3C27'—C22'—C21'122.4 (7)
C10—C11—H11121.3C24'—C23'—C22'120.0
C13—C12—F1119.3 (7)C24'—C23'—H23'120.0
C13—C12—C11123.6 (7)C22'—C23'—H23'120.0
F1—C12—C11117.0 (7)C25'—C24'—C23'120.0
C12—C13—C14117.5 (6)C25'—C24'—H24'120.0
C12—C13—H13121.3C23'—C24'—H24'120.0
C14—C13—H13121.3C26'—C25'—C24'120.0
C13—C14—C9123.0 (6)C26'—C25'—O1113.7 (9)
C13—C14—H14118.5C24'—C25'—O1124.5 (8)
C9—C14—H14118.5C25'—C26'—C27'120.0
N3—C15—C19108.4 (5)C25'—C26'—H26'120.0
N3—C15—C16112.1 (4)C27'—C26'—H26'120.0
C19—C15—C16109.7 (4)C26'—C27'—C22'120.0
N3—C15—H15108.9C26'—C27'—H27'120.0
C19—C15—H15108.9C22'—C27'—H27'120.0
C16—C15—H15108.9O1—C28—H28A109.5
C17—C16—C15110.0 (4)O1—C28—H28B109.5
C17—C16—H16A109.7H28A—C28—H28B109.5
C15—C16—H16A109.7O1—C28—H28C109.5
C17—C16—H16B109.7H28A—C28—H28C109.5
C15—C16—H16B109.7H28B—C28—H28C109.5
Cl2—Co1—Cl1—Cl1'178 (2)C18—N4—C17—C1659.2 (6)
Cl4—Co1—Cl1—Cl1'61 (2)C20—N4—C17—C16173.8 (12)
Cl3—Co1—Cl1—Cl1'68.5 (19)C15—C16—C17—N458.2 (6)
Cl2—Co1—Cl1'—Cl13 (2)C20'—N4—C18—C19167.4 (11)
Cl4—Co1—Cl1'—Cl1124 (2)C17—N4—C18—C1957.8 (6)
Cl3—Co1—Cl1'—Cl1116.1 (18)C20—N4—C18—C19174.2 (11)
C15—N3—C1—N25.4 (8)N4—C18—C19—C1556.8 (7)
C15—N3—C1—N1173.4 (4)N3—C15—C19—C18178.3 (4)
C2—N2—C1—N3179.4 (5)C16—C15—C19—C1855.6 (6)
C2—N2—C1—N10.6 (6)C20'—N4—C20—C2120 (4)
C7—N1—C1—N3180.0 (5)C17—N4—C20—C21168.4 (14)
C8—N1—C1—N32.9 (8)C18—N4—C20—C2171 (2)
C7—N1—C1—N21.1 (5)N4—C20—C21—C22169.4 (11)
C8—N1—C1—N2176.0 (4)C20—C21—C22—C2338.8 (16)
C1—N2—C2—C3177.4 (5)C20—C21—C22—C27144.2 (13)
C1—N2—C2—C70.2 (5)C27—C22—C23—C240.0
C7—C2—C3—C40.2 (8)C21—C22—C23—C24177.0 (8)
N2—C2—C3—C4177.0 (5)C22—C23—C24—C250.0
C2—C3—C4—C50.7 (8)C25'—O1—C25—C26157 (6)
C3—C4—C5—C61.6 (8)C28—O1—C25—C26164.2 (5)
C4—C5—C6—C71.5 (8)C25'—O1—C25—C249 (5)
C5—C6—C7—C20.6 (7)C28—O1—C25—C2429.2 (10)
C5—C6—C7—N1178.8 (5)C23—C24—C25—O1166.7 (9)
C3—C2—C7—C60.3 (8)C23—C24—C25—C260.0
N2—C2—C7—C6177.7 (4)O1—C25—C26—C27166.3 (9)
C3—C2—C7—N1178.4 (5)C24—C25—C26—C270.0
N2—C2—C7—N10.9 (5)C25—C26—C27—C220.0
C1—N1—C7—C6177.2 (5)C23—C22—C27—C260.0
C8—N1—C7—C65.7 (8)C21—C22—C27—C26177.1 (7)
C1—N1—C7—C21.3 (5)C17—N4—C20'—C21'68 (2)
C8—N1—C7—C2175.9 (4)C18—N4—C20'—C21'165.3 (12)
C1—N1—C8—C986.4 (6)C20—N4—C20'—C21'59 (5)
C7—N1—C8—C990.2 (6)N4—C20'—C21'—C22'179.2 (11)
N1—C8—C9—C1083.6 (6)C20'—C21'—C22'—C23'93.2 (13)
N1—C8—C9—C1498.8 (6)C20'—C21'—C22'—C27'84.5 (13)
C14—C9—C10—C110.8 (9)C27'—C22'—C23'—C24'0.0
C8—C9—C10—C11178.6 (5)C21'—C22'—C23'—C24'177.7 (8)
C9—C10—C11—C120.6 (10)C22'—C23'—C24'—C25'0.0
C10—C11—C12—C130.3 (11)C23'—C24'—C25'—C26'0.0
C10—C11—C12—F1178.3 (6)C23'—C24'—C25'—O1163.5 (11)
F1—C12—C13—C14178.4 (5)C25—O1—C25'—C26'32 (5)
C11—C12—C13—C140.1 (11)C28—O1—C25'—C26'177.0 (5)
C12—C13—C14—C90.3 (9)C25—O1—C25'—C24'132 (6)
C10—C9—C14—C130.6 (9)C28—O1—C25'—C24'12.7 (11)
C8—C9—C14—C13178.4 (5)C24'—C25'—C26'—C27'0.0
C1—N3—C15—C19144.2 (5)O1—C25'—C26'—C27'165.2 (9)
C1—N3—C15—C1694.5 (6)C25'—C26'—C27'—C22'0.0
N3—C15—C16—C17175.6 (5)C23'—C22'—C27'—C26'0.0
C19—C15—C16—C1755.2 (6)C21'—C22'—C27'—C26'177.6 (8)
C20'—N4—C17—C16177.7 (14)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N2—H2···Cl2i0.882.283.154 (5)170
N3—H3···Cl30.882.423.212 (5)150
N4—H4···Cl40.932.193.109 (5)171
Symmetry code: (i) x1, y, z.
 

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