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The title compound, [CoCl2(C17H28N4O2)](CH3O4S), is formed from the esterification of the parent benzoic acid complex in refluxing methanol/sulfuric acid. The coordination around cobalt is distorted octahedral, with cis chloride ligands.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536803020099/lh6106sup1.cif
Contains datablocks global, I

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536803020099/lh6106Isup2.hkl
Contains datablock I

CCDC reference: 225676

Key indicators

  • Single-crystal X-ray study
  • T = 103 K
  • Mean [sigma](C-C) = 0.003 Å
  • R factor = 0.034
  • wR factor = 0.098
  • Data-to-parameter ratio = 19.0

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
Author Response: The largest Ueq's are in the region of C20 to C23. This terminal group off of a phenyl ring doesn't interact with any other atoms in the crystal structure. Thus even in this low temperature structure the thermal paramertes increase towards the end of this chain although the elipsoids themselves are not disotted and have resonable orientations.
PLAT222_ALERT_3_A Large Non-Solvent    H     Ueq(max)/Ueq(min) ...       6.12 Ratio
Author Response: (see above) these are the riding hydrogens on C23 in the group described above.

Alert level C PLAT029_ALERT_3_C _diffrn_measured_fraction_theta_full Low ....... 0.99 PLAT063_ALERT_3_C Crystal Probably too Large for Beam Size ....... 0.61 mm PLAT232_ALERT_2_C Hirshfeld Test Diff (M-X) Co - Cl1 = 6.90 su PLAT720_ALERT_4_C Number of Unusual/Non-Standard Label(s) ........ 3
2 ALERT level A = In general: serious problem 0 ALERT level B = Potentially serious problem 4 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 2 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 1 ALERT type 4 Improvement, methodology, query or suggestion

Computing details top

Data collection: SMART (Bruker, 1999); cell refinement: SMART; data reduction: SAINT (Bruker, 2000), XPREP (Bruker, 1997); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: SHELXTL (Bruker, 2000); software used to prepare material for publication: SHELXTL.

(I) top
Crystal data top
[Co(C17H28N4O2)Cl2]·CH3O4SZ = 2
Mr = 561.37F(000) = 584
Triclinic, P1Dx = 1.561 Mg m3
Hall symbol: -P 1Mo Kα radiation, λ = 0.71073 Å
a = 8.0250 (5) ÅCell parameters from 8842 reflections
b = 8.2310 (5) Åθ = 2.2–29.0°
c = 18.7105 (11) ŵ = 1.07 mm1
α = 79.067 (1)°T = 103 K
β = 80.884 (1)°Prism, purple
γ = 83.636 (1)°0.61 × 0.20 × 0.18 mm
V = 1193.97 (13) Å3
Data collection top
Bruker SMART 1000 CCD
diffractometer
5701 independent reflections
Radiation source: sealed tube5017 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.025
φ and ω scansθmax = 29.0°, θmin = 1.1°
Absorption correction: multi-scan
(SADABS; Bruker, 2000)
h = 109
Tmin = 0.695, Tmax = 0.824k = 1110
12393 measured reflectionsl = 2425
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)] = 0.034Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.098H atoms treated by a mixture of independent and constrained refinement
S = 0.96 w = 1/[σ2(Fo2) + (0.0608P)2 + 0.977P]
where P = (Fo2 + 2Fc2)/3
5700 reflections(Δ/σ)max = 0.001
300 parametersΔρmax = 0.89 e Å3
0 restraintsΔρmin = 0.50 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
Co0.45115 (3)0.57761 (3)0.144491 (13)0.01273 (8)
Cl10.24456 (6)0.69652 (6)0.07504 (3)0.02035 (11)
Cl20.39295 (6)0.32742 (6)0.12132 (2)0.01755 (11)
N10.3089 (2)0.5669 (2)0.24589 (9)0.0156 (3)
C20.3092 (3)0.7336 (2)0.27026 (11)0.0198 (4)
H2A0.19670.76310.29710.024*
H2B0.39470.72570.30380.024*
C30.3498 (3)0.8659 (2)0.20382 (11)0.0207 (4)
H3A0.25290.89330.17560.025*
H3B0.37630.96810.21880.025*
N40.4989 (2)0.7945 (2)0.15915 (9)0.0170 (3)
H40.585 (3)0.790 (3)0.1837 (14)0.020*
C50.5508 (3)0.8970 (2)0.08651 (11)0.0214 (4)
H5A0.59730.99930.09250.026*
H5B0.45280.92890.05910.026*
C60.6849 (3)0.7900 (3)0.04603 (12)0.0219 (4)
H6A0.69770.83490.00730.026*
H6B0.79510.79120.06330.026*
N70.6345 (2)0.6139 (2)0.05972 (9)0.0170 (3)
H70.602 (3)0.600 (3)0.0198 (15)0.020*
C80.7821 (2)0.4934 (3)0.07730 (11)0.0202 (4)
H8A0.88710.53090.04610.024*
H8B0.76430.38240.06820.024*
C90.7968 (2)0.4851 (2)0.15789 (11)0.0177 (4)
H9A0.88300.39600.17420.021*
H9B0.82820.59210.16650.021*
N100.6262 (2)0.4491 (2)0.19742 (9)0.0143 (3)
H100.615 (3)0.356 (3)0.1919 (14)0.017*
C110.5895 (2)0.4546 (2)0.27718 (10)0.0167 (4)
H11A0.61680.56180.28720.020*
H11B0.65540.36310.30570.020*
C120.4006 (2)0.4351 (2)0.29650 (10)0.0171 (4)
H12A0.37640.32350.29050.021*
H12B0.36220.44740.34830.021*
C130.1297 (2)0.5284 (3)0.24569 (11)0.0204 (4)
H13A0.13300.44370.21420.025*
H13B0.06720.63020.22260.025*
C140.0302 (3)0.4660 (3)0.32012 (11)0.0211 (4)
C150.0191 (3)0.2959 (3)0.34254 (13)0.0282 (5)
H15A0.08330.22140.31360.034*
C160.0842 (3)0.2326 (3)0.40668 (14)0.0336 (5)
H16A0.09140.11620.42080.040*
C170.1766 (3)0.3404 (3)0.44990 (12)0.0301 (5)
C180.1645 (3)0.5114 (3)0.42879 (12)0.0280 (5)
H18A0.22600.58540.45870.034*
C190.0628 (3)0.5736 (3)0.36423 (12)0.0249 (4)
H19A0.05640.69010.35000.030*
C200.2973 (4)0.2804 (4)0.51714 (13)0.0379 (6)
O210.3696 (3)0.3664 (3)0.55986 (10)0.0427 (5)
O220.3185 (3)0.1178 (3)0.52328 (12)0.0619 (7)
C230.4380 (6)0.0445 (6)0.5876 (2)0.0802 (14)
H23A0.45800.06770.58230.104*
H23B0.54560.11380.58980.104*
H23C0.38920.03930.63280.104*
S0.81037 (7)0.00403 (6)0.23169 (3)0.02219 (12)
O10.9664 (2)0.0071 (2)0.25846 (10)0.0321 (4)
O20.6594 (2)0.0750 (2)0.26772 (10)0.0337 (4)
O30.7910 (2)0.17199 (18)0.22117 (10)0.0291 (4)
O40.82127 (19)0.10897 (19)0.15025 (9)0.0262 (3)
C4A0.9755 (3)0.0833 (3)0.10085 (14)0.0303 (5)
H4AA0.95910.13630.05070.039*
H4AB1.00470.03600.10250.039*
H4AC1.06750.13220.11590.039*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Co0.01322 (13)0.01300 (13)0.01269 (13)0.00030 (9)0.00398 (9)0.00304 (9)
Cl10.0198 (2)0.0243 (2)0.0178 (2)0.00428 (18)0.00830 (17)0.00447 (17)
Cl20.0198 (2)0.0169 (2)0.0182 (2)0.00360 (17)0.00524 (17)0.00556 (16)
N10.0139 (7)0.0193 (8)0.0145 (7)0.0005 (6)0.0039 (6)0.0044 (6)
C20.0227 (10)0.0196 (9)0.0187 (9)0.0018 (7)0.0046 (7)0.0080 (7)
C30.0223 (10)0.0170 (9)0.0227 (10)0.0025 (7)0.0028 (8)0.0061 (7)
N40.0197 (8)0.0147 (7)0.0165 (8)0.0004 (6)0.0037 (6)0.0028 (6)
C50.0266 (10)0.0153 (9)0.0214 (10)0.0032 (8)0.0030 (8)0.0005 (7)
C60.0252 (10)0.0191 (9)0.0213 (10)0.0060 (8)0.0016 (8)0.0021 (7)
N70.0187 (8)0.0184 (8)0.0150 (8)0.0035 (6)0.0027 (6)0.0040 (6)
C80.0172 (9)0.0221 (10)0.0218 (9)0.0005 (7)0.0014 (7)0.0075 (8)
C90.0141 (8)0.0181 (9)0.0221 (9)0.0004 (7)0.0039 (7)0.0060 (7)
N100.0155 (7)0.0125 (7)0.0166 (7)0.0002 (6)0.0053 (6)0.0049 (6)
C110.0177 (9)0.0168 (9)0.0170 (9)0.0002 (7)0.0072 (7)0.0036 (7)
C120.0186 (9)0.0176 (9)0.0155 (9)0.0009 (7)0.0054 (7)0.0015 (7)
C130.0139 (9)0.0309 (11)0.0180 (9)0.0023 (8)0.0032 (7)0.0072 (8)
C140.0168 (9)0.0296 (11)0.0187 (9)0.0035 (8)0.0040 (7)0.0065 (8)
C150.0269 (11)0.0298 (11)0.0298 (11)0.0062 (9)0.0021 (9)0.0130 (9)
C160.0369 (13)0.0302 (12)0.0331 (13)0.0116 (10)0.0018 (10)0.0044 (10)
C170.0315 (12)0.0413 (13)0.0189 (10)0.0110 (10)0.0015 (9)0.0058 (9)
C180.0274 (11)0.0374 (12)0.0191 (10)0.0008 (9)0.0001 (8)0.0088 (9)
C190.0232 (10)0.0294 (11)0.0208 (10)0.0007 (8)0.0017 (8)0.0041 (8)
C200.0422 (14)0.0529 (16)0.0209 (11)0.0204 (12)0.0012 (10)0.0052 (11)
O210.0456 (11)0.0612 (13)0.0201 (8)0.0124 (9)0.0050 (8)0.0076 (8)
O220.0860 (18)0.0648 (15)0.0366 (11)0.0461 (14)0.0195 (11)0.0131 (10)
C230.115 (4)0.085 (3)0.0444 (19)0.061 (3)0.014 (2)0.0116 (19)
S0.0225 (2)0.0147 (2)0.0313 (3)0.00114 (18)0.0075 (2)0.00744 (19)
O10.0292 (9)0.0314 (9)0.0415 (10)0.0011 (7)0.0137 (7)0.0144 (7)
O20.0296 (9)0.0227 (8)0.0449 (10)0.0037 (7)0.0014 (7)0.0048 (7)
O30.0359 (9)0.0145 (7)0.0415 (9)0.0002 (6)0.0188 (7)0.0065 (6)
O40.0220 (7)0.0204 (7)0.0338 (9)0.0043 (6)0.0045 (6)0.0020 (6)
C4A0.0250 (11)0.0308 (12)0.0335 (12)0.0060 (9)0.0031 (9)0.0071 (9)
Geometric parameters (Å, º) top
Co—N41.9444 (17)C11—C121.520 (3)
Co—N101.9462 (16)C11—H11A0.9900
Co—N71.9868 (17)C11—H11B0.9900
Co—N12.0453 (16)C12—H12A0.9900
Co—Cl12.2882 (5)C12—H12B0.9900
Co—Cl22.2940 (5)C13—C141.519 (3)
N1—C121.507 (2)C13—H13A0.9900
N1—C131.507 (2)C13—H13B0.9900
N1—C21.526 (2)C14—C151.392 (3)
C2—C31.508 (3)C14—C191.399 (3)
C2—H2A0.9900C15—C161.394 (3)
C2—H2B0.9900C15—H15A0.9500
C3—N41.480 (3)C16—C171.389 (4)
C3—H3A0.9900C16—H16A0.9500
C3—H3B0.9900C17—C181.398 (3)
N4—C51.482 (2)C17—C201.500 (3)
N4—H40.88 (3)C18—C191.390 (3)
C5—C61.515 (3)C18—H18A0.9500
C5—H5A0.9900C19—H19A0.9500
C5—H5B0.9900C20—O211.205 (3)
C6—N71.512 (3)C20—O221.349 (4)
C6—H6A0.9900O22—C231.489 (4)
C6—H6B0.9900C23—H23A0.9800
N7—C81.495 (3)C23—H23B0.9800
N7—H70.86 (3)C23—H23C0.9800
C8—C91.519 (3)S—O11.4384 (17)
C8—H8A0.9900S—O21.4418 (17)
C8—H8B0.9900S—O31.4611 (15)
C9—N101.481 (2)S—O41.6226 (17)
C9—H9A0.9900O4—C4A1.444 (3)
C9—H9B0.9900C4A—H4AA0.9800
N10—C111.483 (2)C4A—H4AB0.9800
N10—H100.81 (3)C4A—H4AC0.9800
N4—Co—N1096.74 (7)C8—C9—H9B110.8
N4—Co—N783.89 (7)H9A—C9—H9B108.9
N10—Co—N785.46 (7)C9—N10—C11118.87 (15)
N4—Co—N184.23 (7)C9—N10—Co110.64 (12)
N10—Co—N185.19 (7)C11—N10—Co111.37 (12)
N7—Co—N1163.90 (7)C9—N10—H10104.5 (18)
N4—Co—Cl190.92 (5)C11—N10—H10108.1 (18)
N10—Co—Cl1171.96 (5)Co—N10—H10101.6 (18)
N7—Co—Cl192.97 (5)N10—C11—C12104.35 (15)
N1—Co—Cl198.06 (5)N10—C11—H11A110.9
N4—Co—Cl2177.16 (5)C12—C11—H11A110.9
N10—Co—Cl285.40 (5)N10—C11—H11B110.9
N7—Co—Cl294.45 (5)C12—C11—H11B110.9
N1—Co—Cl297.82 (5)H11A—C11—H11B108.9
Cl1—Co—Cl286.867 (19)N1—C12—C11108.26 (15)
C12—N1—C13111.78 (15)N1—C12—H12A110.0
C12—N1—C2108.72 (14)C11—C12—H12A110.0
C13—N1—C2110.13 (15)N1—C12—H12B110.0
C12—N1—Co105.53 (11)C11—C12—H12B110.0
C13—N1—Co112.33 (12)H12A—C12—H12B108.4
C2—N1—Co108.16 (12)N1—C13—C14116.35 (16)
C3—C2—N1109.59 (16)N1—C13—H13A108.2
C3—C2—H2A109.8C14—C13—H13A108.2
N1—C2—H2A109.8N1—C13—H13B108.2
C3—C2—H2B109.8C14—C13—H13B108.2
N1—C2—H2B109.8H13A—C13—H13B107.4
H2A—C2—H2B108.2C15—C14—C19118.5 (2)
N4—C3—C2105.58 (16)C15—C14—C13118.8 (2)
N4—C3—H3A110.6C19—C14—C13122.42 (19)
C2—C3—H3A110.6C14—C15—C16121.3 (2)
N4—C3—H3B110.6C14—C15—H15A119.3
C2—C3—H3B110.6C16—C15—H15A119.3
H3A—C3—H3B108.8C17—C16—C15119.7 (2)
C3—N4—C5115.03 (16)C17—C16—H16A120.1
C3—N4—Co108.64 (12)C15—C16—H16A120.1
C5—N4—Co108.85 (13)C16—C17—C18119.7 (2)
C3—N4—H4106.0 (16)C16—C17—C20122.1 (2)
C5—N4—H4105.1 (16)C18—C17—C20118.2 (2)
Co—N4—H4113.3 (16)C19—C18—C17120.3 (2)
N4—C5—C6105.98 (16)C19—C18—H18A119.9
N4—C5—H5A110.5C17—C18—H18A119.9
C6—C5—H5A110.5C18—C19—C14120.5 (2)
N4—C5—H5B110.5C18—C19—H19A119.7
C6—C5—H5B110.5C14—C19—H19A119.7
H5A—C5—H5B108.7O21—C20—O22123.7 (2)
N7—C6—C5109.69 (16)O21—C20—C17124.7 (3)
N7—C6—H6A109.7O22—C20—C17111.5 (2)
C5—C6—H6A109.7C20—O22—C23116.4 (3)
N7—C6—H6B109.7O22—C23—H23A109.5
C5—C6—H6B109.7O22—C23—H23B109.5
H6A—C6—H6B108.2H23A—C23—H23B109.5
C8—N7—C6110.29 (15)O22—C23—H23C109.5
C8—N7—Co107.62 (12)H23A—C23—H23C109.5
C6—N7—Co110.91 (13)H23B—C23—H23C109.5
C8—N7—H7110.6 (17)O1—S—O2116.68 (11)
C6—N7—H7106.1 (16)O1—S—O3112.35 (10)
Co—N7—H7111.4 (17)O2—S—O3113.77 (10)
N7—C8—C9107.48 (16)O1—S—O4106.74 (10)
N7—C8—H8A110.2O2—S—O4100.20 (9)
C9—C8—H8A110.2O3—S—O4105.40 (9)
N7—C8—H8B110.2C4A—O4—S116.14 (13)
C9—C8—H8B110.2O4—C4A—H4AA109.5
H8A—C8—H8B108.5O4—C4A—H4AB109.5
N10—C9—C8104.77 (15)H4AA—C4A—H4AB109.5
N10—C9—H9A110.8O4—C4A—H4AC109.5
C8—C9—H9A110.8H4AA—C4A—H4AC109.5
N10—C9—H9B110.8H4AB—C4A—H4AC109.5
N4—Co—N1—C12111.33 (12)Cl2—Co—N7—C6168.16 (12)
N10—Co—N1—C1214.04 (12)C6—N7—C8—C980.84 (19)
N7—Co—N1—C1268.7 (3)Co—N7—C8—C940.27 (17)
Cl1—Co—N1—C12158.56 (11)N7—C8—C9—N1052.88 (19)
Cl2—Co—N1—C1270.64 (11)C8—C9—N10—C11172.00 (16)
N4—Co—N1—C13126.64 (14)C8—C9—N10—Co41.28 (17)
N10—Co—N1—C13136.07 (14)N4—Co—N10—C967.28 (13)
N7—Co—N1—C13169.3 (2)N7—Co—N10—C916.00 (13)
Cl1—Co—N1—C1336.52 (13)N1—Co—N10—C9150.88 (13)
Cl2—Co—N1—C1351.40 (13)Cl2—Co—N10—C9110.85 (12)
N4—Co—N1—C24.88 (12)N4—Co—N10—C1167.26 (13)
N10—Co—N1—C2102.18 (12)N7—Co—N10—C11150.54 (13)
N7—Co—N1—C247.5 (3)N1—Co—N10—C1116.34 (12)
Cl1—Co—N1—C285.23 (11)C9—N10—C11—C12172.67 (15)
Cl2—Co—N1—C2173.15 (11)Co—N10—C11—C1242.28 (16)
C12—N1—C2—C3136.45 (16)C13—N1—C12—C11163.58 (16)
C13—N1—C2—C3100.76 (18)C2—N1—C12—C1174.64 (18)
Co—N1—C2—C322.33 (18)Co—N1—C12—C1141.19 (17)
N1—C2—C3—N447.4 (2)N10—C11—C12—N154.65 (19)
C2—C3—N4—C5173.78 (16)C12—N1—C13—C1443.5 (2)
C2—C3—N4—Co51.52 (17)C2—N1—C13—C1477.5 (2)
N10—Co—N4—C3116.16 (13)Co—N1—C13—C14161.90 (15)
N7—Co—N4—C3159.17 (13)N1—C13—C14—C1598.0 (2)
N1—Co—N4—C331.72 (12)N1—C13—C14—C1987.6 (2)
Cl1—Co—N4—C366.29 (12)C19—C14—C15—C161.2 (3)
N10—Co—N4—C5117.90 (13)C13—C14—C15—C16173.4 (2)
N7—Co—N4—C533.23 (13)C14—C15—C16—C170.9 (4)
N1—Co—N4—C5157.66 (14)C15—C16—C17—C180.3 (4)
Cl1—Co—N4—C559.66 (13)C15—C16—C17—C20176.5 (2)
C3—N4—C5—C6171.19 (16)C16—C17—C18—C191.1 (4)
Co—N4—C5—C649.04 (18)C20—C17—C18—C19175.8 (2)
N4—C5—C6—N740.9 (2)C17—C18—C19—C140.8 (3)
C5—C6—N7—C8134.57 (17)C15—C14—C19—C180.3 (3)
C5—C6—N7—Co15.4 (2)C13—C14—C19—C18174.08 (19)
N4—Co—N7—C8111.19 (13)C16—C17—C20—O21173.4 (3)
N10—Co—N7—C813.90 (13)C18—C17—C20—O219.8 (4)
N1—Co—N7—C868.5 (3)C16—C17—C20—O228.0 (4)
Cl1—Co—N7—C8158.21 (12)C18—C17—C20—O22168.8 (2)
Cl2—Co—N7—C871.12 (12)O21—C20—O22—C230.5 (5)
N4—Co—N7—C69.53 (13)C17—C20—O22—C23179.1 (3)
N10—Co—N7—C6106.82 (13)O1—S—O4—C4A48.05 (18)
N1—Co—N7—C652.2 (3)O2—S—O4—C4A170.09 (16)
Cl1—Co—N7—C681.08 (13)O3—S—O4—C4A71.60 (17)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N4—H4···O3i0.88 (3)1.97 (2)2.836 (2)166 (2)
N10—H10···O20.81 (2)2.49 (3)3.111 (2)134 (2)
N7—H7···Cl2ii0.86 (3)2.59 (3)3.3687 (17)151 (2)
Symmetry codes: (i) x, y+1, z; (ii) x+1, y+1, z.
 

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