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The title compound, [CuCl(NO3)(C33H39N3)] or Cu([9]­ane(Nvbz)3NO3Cl, is the polymerizable form of a potent metal-chelator complex that catalyses the hydro­lysis of phosphate esters. The coordination geometry around the Cu atom is square pyramidal. The structure has a similar conformation to the parent catalyst Cu([9]­aneN3)Cl2, showing that the extensive functionalization does not significantly distort the metal-complex geometry.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536802011613/ob6143sup1.cif
Contains datablocks global, I

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536802011613/ob6143Isup2.hkl
Contains datablock I

CCDC reference: 169486

Key indicators

  • Single-crystal X-ray study
  • T = 93 K
  • Mean [sigma](C-C) = 0.003 Å
  • R factor = 0.023
  • wR factor = 0.064
  • Data-to-parameter ratio = 14.8

checkCIF results

No syntax errors found

ADDSYM reports no extra symmetry

General Notes

REFLT_03 From the CIF: _diffrn_reflns_theta_max 28.29 From the CIF: _reflns_number_total 5597 Count of symmetry unique reflns 3799 Completeness (_total/calc) 147.33% TEST3: Check Friedels for noncentro structure Estimate of Friedel pairs measured 1798 Fraction of Friedel pairs measured 0.473 Are heavy atom types Z>Si present yes WARNING: Large fraction of Friedel related reflns may be needed to determine absolute structure

Computing details top

Data collection: SMART (Bruker, 1999); cell refinement: SMART; data reduction: SAINT (Bruker, 2000) and 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.

Chloro(nitrato)[1,4,7-tris(4-vinyl)benzyl-1,4,7-triazacyclononane]copper(II) top
Crystal data top
[CuCl(NO3)(C33H39N3)]F(000) = 1340
Mr = 638.67Dx = 1.383 Mg m3
Monoclinic, CcMo Kα radiation, λ = 0.71073 Å
a = 9.7764 (10) ÅCell parameters from 5031 reflections
b = 28.491 (3) Åθ = 4.7–56.5°
c = 11.2790 (12) ŵ = 0.84 mm1
β = 102.437 (2)°T = 93 K
V = 3068.0 (6) Å3Prism, blue
Z = 40.35 × 0.20 × 0.10 mm
Data collection top
Bruker SMART 1000 CCD
diffractometer
5597 independent reflections
Radiation source: sealed tube5414 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.014
φ and ω scansθmax = 28.3°, θmin = 1.4°
Absorption correction: integration
(XPREP; Bruker, 1997)
h = 1213
Tmin = 0.68, Tmax = 0.87k = 3637
10947 measured reflectionsl = 1414
Refinement top
Refinement on F2Secondary atom site location: difference Fourier map
Least-squares matrix: fullHydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.023H-atom parameters constrained
wR(F2) = 0.064 w = 1/[σ2(Fo2) + (0.0335P)2 + 1.7291P]
where P = (Fo2 + 2Fc2)/3
S = 0.88(Δ/σ)max = 0.001
5597 reflectionsΔρmax = 0.35 e Å3
379 parametersΔρmin = 0.22 e Å3
2 restraintsAbsolute structure: (Flack, 1983), 1798 Friedel pairs
Primary atom site location: structure-invariant direct methodsAbsolute structure parameter: 0.011 (6)
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
Cu10.73600 (2)0.13864 (1)0.49083 (2)0.01610 (6)
N10.81315 (16)0.19164 (6)0.40219 (15)0.0168 (3)
C20.68483 (19)0.21137 (7)0.32228 (18)0.0199 (4)
H2A0.71150.23480.26920.024*
H2B0.62840.22670.37190.024*
C30.59752 (19)0.17305 (7)0.24517 (18)0.0204 (4)
H3A0.50870.18620.20320.025*
H3B0.64670.16190.18450.025*
N40.57174 (17)0.13337 (5)0.32109 (16)0.0197 (3)
C50.6019 (2)0.08664 (7)0.27555 (19)0.0226 (4)
H5A0.54940.08300.19270.027*
H5B0.57080.06260.32460.027*
C60.7579 (2)0.07986 (7)0.27910 (19)0.0222 (4)
H6A0.77490.04710.26430.027*
H6B0.78280.09810.21420.027*
N70.85058 (17)0.09432 (6)0.39781 (15)0.0185 (3)
C80.9665 (2)0.12482 (7)0.37834 (18)0.0199 (4)
H8A1.01490.10980.32190.024*
H8B1.03320.12940.45470.024*
C90.90960 (18)0.17208 (7)0.32793 (17)0.0183 (4)
H9A0.98660.19370.32920.022*
H9B0.85940.16840.24440.022*
C100.9082 (2)0.05282 (7)0.47540 (18)0.0227 (4)
H10A0.83640.02880.46480.027*
H10B0.92660.06250.55980.027*
C111.0407 (2)0.03107 (7)0.45035 (18)0.0227 (4)
C121.1706 (2)0.04569 (7)0.51966 (19)0.0250 (4)
H12A1.17290.06870.57860.030*
C131.2947 (2)0.02684 (7)0.5026 (2)0.0262 (4)
H13A1.37920.03700.55040.031*
C141.2945 (2)0.00735 (7)0.4142 (2)0.0264 (4)
C151.1656 (3)0.02244 (7)0.3460 (2)0.0290 (4)
H15A1.16330.04550.28730.035*
C161.0405 (2)0.00362 (7)0.36398 (19)0.0277 (4)
H16A0.95590.01440.31770.033*
C171.4263 (3)0.02772 (8)0.3921 (2)0.0318 (5)
H17A1.42050.04440.32030.038*
C181.5505 (2)0.02441 (8)0.4644 (2)0.0334 (5)
H18A1.56140.00810.53730.040*
H18B1.62760.03840.44290.040*
C190.88762 (19)0.23016 (7)0.48259 (18)0.0196 (4)
H19A0.82480.24330.52960.023*
H19B0.91290.25500.43240.023*
C201.01820 (19)0.21224 (6)0.56786 (18)0.0190 (4)
C211.1499 (2)0.21804 (7)0.54098 (18)0.0205 (4)
H21A1.15840.23530.47300.025*
C221.2687 (2)0.19839 (7)0.61444 (19)0.0223 (4)
H22A1.35520.20210.59380.027*
C231.2601 (2)0.17318 (7)0.71861 (19)0.0211 (4)
C241.1280 (2)0.16764 (7)0.74641 (19)0.0221 (4)
H24A1.11960.15080.81510.027*
C251.0096 (2)0.18702 (7)0.67247 (19)0.0211 (4)
H25A0.92300.18320.69280.025*
C261.3891 (2)0.15483 (8)0.7983 (2)0.0273 (4)
H26A1.46680.15090.76410.033*
C271.4037 (3)0.14354 (8)0.9135 (2)0.0306 (5)
H27A1.32870.14690.95140.037*
H27B1.48910.13220.95700.037*
C280.4331 (2)0.13617 (7)0.35569 (18)0.0214 (4)
H28A0.43120.16460.40270.026*
H28B0.42550.10980.40840.026*
C290.3056 (2)0.13611 (7)0.25244 (18)0.0208 (4)
C300.2483 (2)0.09432 (7)0.19978 (19)0.0235 (4)
H30A0.29200.06590.22490.028*
C310.1262 (2)0.09482 (8)0.11006 (19)0.0256 (4)
H31A0.08940.06670.07530.031*
C320.0574 (2)0.13702 (8)0.0709 (2)0.0250 (5)
C330.1173 (2)0.17883 (8)0.12155 (19)0.0258 (4)
H33A0.07570.20740.09470.031*
C340.2386 (2)0.17807 (7)0.21167 (19)0.0231 (4)
H34A0.27620.20620.24570.028*
C350.0763 (2)0.13590 (10)0.0203 (2)0.0351 (5)
H35A0.10070.10760.06020.042*
C360.1637 (3)0.17093 (13)0.0503 (3)0.0520 (8)
H36A0.14390.20000.01290.062*
H36B0.24560.16670.10900.062*
N20.7202 (2)0.07331 (7)0.67013 (17)0.0264 (4)
O10.83070 (16)0.09329 (6)0.71528 (14)0.0291 (3)
O20.65605 (15)0.08391 (5)0.56098 (13)0.0227 (3)
O30.6682 (2)0.04239 (7)0.72359 (16)0.0424 (4)
Cl10.64140 (5)0.18881 (2)0.61001 (5)0.02386 (11)
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Cu10.01574 (9)0.01914 (10)0.01308 (10)0.00109 (9)0.00233 (7)0.00179 (9)
N10.0168 (7)0.0179 (8)0.0154 (8)0.0014 (6)0.0027 (6)0.0019 (6)
C20.0185 (8)0.0224 (9)0.0182 (9)0.0006 (7)0.0023 (7)0.0034 (7)
C30.0186 (8)0.0258 (9)0.0160 (9)0.0003 (7)0.0019 (7)0.0045 (7)
N40.0197 (8)0.0226 (8)0.0161 (8)0.0031 (6)0.0025 (6)0.0022 (6)
C50.0230 (9)0.0250 (10)0.0183 (10)0.0047 (7)0.0009 (8)0.0008 (8)
C60.0268 (10)0.0220 (9)0.0158 (9)0.0006 (7)0.0005 (8)0.0029 (7)
N70.0208 (7)0.0194 (8)0.0144 (8)0.0010 (6)0.0016 (6)0.0013 (6)
C80.0194 (8)0.0220 (9)0.0186 (9)0.0020 (7)0.0044 (7)0.0008 (7)
C90.0175 (8)0.0232 (9)0.0146 (8)0.0003 (7)0.0043 (7)0.0013 (7)
C100.0252 (9)0.0223 (9)0.0198 (9)0.0014 (7)0.0033 (8)0.0031 (8)
C110.0274 (10)0.0207 (9)0.0194 (10)0.0035 (7)0.0034 (8)0.0035 (7)
C120.0306 (10)0.0224 (10)0.0208 (10)0.0035 (8)0.0033 (8)0.0007 (8)
C130.0320 (10)0.0237 (10)0.0232 (10)0.0010 (8)0.0061 (8)0.0040 (8)
C140.0375 (11)0.0198 (9)0.0230 (10)0.0044 (8)0.0092 (9)0.0055 (8)
C150.0446 (12)0.0211 (9)0.0212 (10)0.0015 (9)0.0067 (9)0.0033 (8)
C160.0355 (11)0.0227 (10)0.0225 (10)0.0009 (8)0.0010 (9)0.0003 (8)
C170.0460 (13)0.0239 (10)0.0308 (12)0.0037 (9)0.0197 (10)0.0008 (8)
C180.0364 (12)0.0267 (11)0.0417 (13)0.0036 (9)0.0187 (11)0.0014 (9)
C190.0184 (8)0.0177 (9)0.0212 (9)0.0009 (7)0.0013 (7)0.0012 (7)
C200.0168 (8)0.0180 (8)0.0206 (9)0.0014 (6)0.0006 (7)0.0035 (7)
C210.0216 (8)0.0226 (9)0.0176 (9)0.0021 (7)0.0049 (7)0.0014 (7)
C220.0162 (8)0.0273 (10)0.0239 (10)0.0000 (7)0.0058 (7)0.0059 (8)
C230.0197 (9)0.0204 (9)0.0221 (10)0.0016 (7)0.0018 (7)0.0052 (7)
C240.0219 (9)0.0226 (9)0.0211 (10)0.0013 (7)0.0031 (8)0.0002 (8)
C250.0178 (8)0.0230 (9)0.0224 (10)0.0035 (7)0.0039 (7)0.0039 (7)
C260.0241 (9)0.0265 (10)0.0300 (11)0.0055 (8)0.0029 (8)0.0009 (9)
C270.0300 (11)0.0284 (12)0.0303 (13)0.0040 (9)0.0002 (10)0.0019 (9)
C280.0191 (9)0.0305 (10)0.0140 (9)0.0046 (7)0.0019 (7)0.0013 (7)
C290.0166 (8)0.0314 (11)0.0141 (9)0.0031 (7)0.0026 (7)0.0008 (7)
C300.0214 (9)0.0275 (10)0.0213 (10)0.0019 (8)0.0038 (7)0.0014 (8)
C310.0248 (9)0.0335 (11)0.0181 (9)0.0072 (8)0.0040 (8)0.0062 (8)
C320.0182 (9)0.0419 (13)0.0148 (10)0.0000 (8)0.0031 (8)0.0011 (8)
C330.0235 (9)0.0344 (11)0.0206 (10)0.0048 (8)0.0071 (8)0.0040 (8)
C340.0226 (9)0.0274 (10)0.0203 (10)0.0035 (8)0.0070 (8)0.0014 (8)
C350.0235 (11)0.0611 (16)0.0192 (11)0.0013 (9)0.0014 (9)0.0064 (10)
C360.0333 (13)0.081 (2)0.0350 (14)0.0156 (13)0.0081 (11)0.0119 (14)
N20.0308 (9)0.0295 (9)0.0194 (9)0.0005 (7)0.0062 (7)0.0040 (7)
O10.0304 (8)0.0323 (8)0.0205 (8)0.0001 (7)0.0034 (6)0.0004 (6)
O20.0240 (7)0.0265 (7)0.0166 (7)0.0041 (5)0.0020 (5)0.0038 (6)
O30.0546 (11)0.0459 (10)0.0283 (9)0.0107 (9)0.0126 (8)0.0159 (8)
Cl10.0187 (2)0.0323 (3)0.0208 (2)0.00056 (18)0.00473 (17)0.00233 (19)
Geometric parameters (Å, º) top
Cu1—O21.9837 (15)C17—C181.312 (3)
Cu1—N12.0428 (17)C17—H17A0.9300
Cu1—N72.1111 (17)C18—H18A0.9300
Cu1—N42.2232 (17)C18—H18B0.9300
Cu1—Cl12.2892 (6)C19—C201.512 (3)
N1—C21.488 (2)C19—H19A0.9700
N1—C91.497 (2)C19—H19B0.9700
N1—C191.508 (2)C20—C211.395 (3)
C2—C31.535 (3)C20—C251.399 (3)
C2—H2A0.9700C21—C221.391 (3)
C2—H2B0.9700C21—H21A0.9300
C3—N41.472 (2)C22—C231.395 (3)
C3—H3A0.9700C22—H22A0.9300
C3—H3B0.9700C23—C241.402 (3)
N4—C51.479 (3)C23—C261.478 (3)
N4—C281.491 (2)C24—C251.387 (3)
C5—C61.529 (3)C24—H24A0.9300
C5—H5A0.9700C25—H25A0.9300
C5—H5B0.9700C26—C271.315 (4)
C6—N71.504 (3)C26—H26A0.9300
C6—H6A0.9700C27—H27A0.9300
C6—H6B0.9700C27—H27B0.9300
N7—C81.482 (3)C28—C291.511 (3)
N7—C101.506 (2)C28—H28A0.9700
C8—C91.520 (3)C28—H28B0.9700
C8—H8A0.9700C29—C341.393 (3)
C8—H8B0.9700C29—C301.393 (3)
C9—H9A0.9700C30—C311.389 (3)
C9—H9B0.9700C30—H30A0.9300
C10—C111.517 (3)C31—C321.402 (3)
C10—H10A0.9700C31—H31A0.9300
C10—H10B0.9700C32—C331.394 (3)
C11—C161.388 (3)C32—C351.480 (3)
C11—C121.403 (3)C33—C341.386 (3)
C12—C131.378 (3)C33—H33A0.9300
C12—H12A0.9300C34—H34A0.9300
C13—C141.394 (3)C35—C361.310 (4)
C13—H13A0.9300C35—H35A0.9300
C14—C151.396 (3)C36—H36A0.9300
C14—C171.483 (3)C36—H36B0.9300
C15—C161.389 (3)N2—O11.230 (2)
C15—H15A0.9300N2—O31.237 (3)
C16—H16A0.9300N2—O21.291 (2)
O2—Cu1—N1174.25 (7)C13—C14—C15118.1 (2)
O2—Cu1—N791.42 (7)C13—C14—C17121.8 (2)
N1—Cu1—N784.70 (7)C15—C14—C17120.1 (2)
O2—Cu1—N490.96 (6)C16—C15—C14121.29 (19)
N1—Cu1—N484.43 (6)C16—C15—H15A119.4
N7—Cu1—N483.90 (6)C14—C15—H15A119.4
O2—Cu1—Cl190.74 (5)C11—C16—C15120.6 (2)
N1—Cu1—Cl193.69 (5)C11—C16—H16A119.7
N7—Cu1—Cl1171.91 (5)C15—C16—H16A119.7
N4—Cu1—Cl1103.86 (5)C18—C17—C14126.0 (2)
C2—N1—C9110.62 (15)C18—C17—H17A117.0
C2—N1—C19108.91 (15)C14—C17—H17A117.0
C9—N1—C19109.07 (14)C17—C18—H18A120.0
C2—N1—Cu1102.93 (11)C17—C18—H18B120.0
C9—N1—Cu1110.01 (12)H18A—C18—H18B120.0
C19—N1—Cu1115.16 (12)N1—C19—C20111.66 (15)
N1—C2—C3111.57 (15)N1—C19—H19A109.3
N1—C2—H2A109.3C20—C19—H19A109.3
C3—C2—H2A109.3N1—C19—H19B109.3
N1—C2—H2B109.3C20—C19—H19B109.3
C3—C2—H2B109.3H19A—C19—H19B107.9
H2A—C2—H2B108.0C21—C20—C25118.04 (17)
N4—C3—C2111.14 (15)C21—C20—C19120.94 (18)
N4—C3—H3A109.4C25—C20—C19120.92 (17)
C2—C3—H3A109.4C22—C21—C20120.97 (18)
N4—C3—H3B109.4C22—C21—H21A119.5
C2—C3—H3B109.4C20—C21—H21A119.5
H3A—C3—H3B108.0C21—C22—C23120.96 (18)
C3—N4—C5114.67 (16)C21—C22—H22A119.5
C3—N4—C28112.96 (15)C23—C22—H22A119.5
C5—N4—C28113.53 (15)C22—C23—C24118.18 (18)
C3—N4—Cu1105.46 (11)C22—C23—C26119.73 (18)
C5—N4—Cu1101.48 (11)C24—C23—C26122.04 (19)
C28—N4—Cu1107.44 (12)C25—C24—C23120.67 (19)
N4—C5—C6112.12 (16)C25—C24—H24A119.7
N4—C5—H5A109.2C23—C24—H24A119.7
C6—C5—H5A109.2C24—C25—C20121.17 (18)
N4—C5—H5B109.2C24—C25—H25A119.4
C6—C5—H5B109.2C20—C25—H25A119.4
H5A—C5—H5B107.9C27—C26—C23125.8 (2)
N7—C6—C5113.28 (17)C27—C26—H26A117.1
N7—C6—H6A108.9C23—C26—H26A117.1
C5—C6—H6A108.9C26—C27—H27A120.0
N7—C6—H6B108.9C26—C27—H27B120.0
C5—C6—H6B108.9H27A—C27—H27B120.0
H6A—C6—H6B107.7N4—C28—C29116.32 (16)
C8—N7—C6111.24 (15)N4—C28—H28A108.2
C8—N7—C10110.14 (15)C29—C28—H28A108.2
C6—N7—C10112.37 (15)N4—C28—H28B108.2
C8—N7—Cu1103.15 (12)C29—C28—H28B108.2
C6—N7—Cu1108.89 (12)H28A—C28—H28B107.4
C10—N7—Cu1110.66 (12)C34—C29—C30118.38 (19)
N7—C8—C9110.17 (15)C34—C29—C28120.30 (18)
N7—C8—H8A109.6C30—C29—C28121.25 (18)
C9—C8—H8A109.6C31—C30—C29120.37 (19)
N7—C8—H8B109.6C31—C30—H30A119.8
C9—C8—H8B109.6C29—C30—H30A119.8
H8A—C8—H8B108.1C30—C31—C32121.1 (2)
N1—C9—C8110.15 (15)C30—C31—H31A119.4
N1—C9—H9A109.6C32—C31—H31A119.4
C8—C9—H9A109.6C33—C32—C31118.2 (2)
N1—C9—H9B109.6C33—C32—C35122.3 (2)
C8—C9—H9B109.6C31—C32—C35119.5 (2)
H9A—C9—H9B108.1C34—C33—C32120.3 (2)
N7—C10—C11116.09 (16)C34—C33—H33A119.8
N7—C10—H10A108.3C32—C33—H33A119.8
C11—C10—H10A108.3C33—C34—C29121.52 (19)
N7—C10—H10B108.3C33—C34—H34A119.2
C11—C10—H10B108.3C29—C34—H34A119.2
H10A—C10—H10B107.4C36—C35—C32126.4 (3)
C16—C11—C12117.85 (19)C36—C35—H35A116.8
C16—C11—C10123.34 (18)C32—C35—H35A116.8
C12—C11—C10118.80 (18)C35—C36—H36A120.0
C13—C12—C11121.6 (2)C35—C36—H36B120.0
C13—C12—H12A119.2H36A—C36—H36B120.0
C11—C12—H12A119.2O1—N2—O3122.98 (19)
C12—C13—C14120.5 (2)O1—N2—O2119.28 (18)
C12—C13—H13A119.8O3—N2—O2117.72 (19)
C14—C13—H13A119.8N2—O2—Cu1114.34 (13)
 

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