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In the title CuI complex, [Cu(C10H9N3)2]ClO4·C6H6, the coordination of the metal ion is tetra­hedral, surrounded by two bidentate di-2-pyridylamine ligands, and coordinated by four N atoms from pyridine rings. The CuI-N bond lengths are shorter than those reported for CuII-N. In this structure, the two ligand mol­ecules are approximately orthogonal.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S160053680602784X/at2057sup1.cif
Contains datablocks global, I

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S160053680602784X/at2057Isup2.hkl
Contains datablock I

CCDC reference: 618113

Key indicators

  • Single-crystal X-ray study
  • T = 273 K
  • Mean [sigma](C-C) = 0.007 Å
  • R factor = 0.050
  • wR factor = 0.122
  • Data-to-parameter ratio = 20.0

checkCIF/PLATON results

No syntax errors found



Alert level C REFLT03_ALERT_3_C Reflection count < 95% complete From the CIF: _diffrn_reflns_theta_max 28.27 From the CIF: _diffrn_reflns_theta_full 28.27 From the CIF: _reflns_number_total 6023 TEST2: Reflns within _diffrn_reflns_theta_max Count of symmetry unique reflns 6652 Completeness (_total/calc) 90.54% PLAT042_ALERT_1_C Calc. and Rep. MoietyFormula Strings Differ .... ? PLAT241_ALERT_2_C Check High Ueq as Compared to Neighbors for N5 PLAT243_ALERT_4_C High 'Solvent' Ueq as Compared to Neighbors for C21 PLAT244_ALERT_4_C Low 'Solvent' Ueq as Compared to Neighbors for Cl1 PLAT341_ALERT_3_C Low Bond Precision on C-C bonds (x 1000) Ang ... 7
Alert level G FORMU01_ALERT_1_G There is a discrepancy between the atom counts in the _chemical_formula_sum and _chemical_formula_moiety. This is usually due to the moiety formula being in the wrong format. Atom count from _chemical_formula_sum: C26 H24 Cl1 Cu1 N6 O4 Atom count from _chemical_formula_moiety:C32 H30 Cl1 Cu1 N6 O4
0 ALERT level A = In general: serious problem 0 ALERT level B = Potentially serious problem 6 ALERT level C = Check and explain 1 ALERT level G = General alerts; check 2 ALERT type 1 CIF construction/syntax error, inconsistent or missing data 1 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 2 ALERT type 4 Improvement, methodology, query or suggestion 0 ALERT type 5 Informative message, check

Computing details top

Data collection: APEX2 (Bruker, 2004); cell refinement: APEX2; data reduction: APEX2; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: APEX2; software used to prepare material for publication: APEX2.

Bis(di-2-pyridylamine)copper(I) perchlorate benzene solvate top
Crystal data top
[Cu(C10H9N3)2]·ClO4·C6H6Z = 8
Mr = 583.50F(000) = 2400
Monoclinic, C2/cDx = 1.447 Mg m3
Hall symbol: -C 2ycMo Kα radiation, λ = 0.71073 Å
a = 14.2353 (9) Åθ = 2.2–28.3°
b = 22.1952 (14) ŵ = 0.96 mm1
c = 18.3608 (15) ÅT = 273 K
β = 112.578 (1)°Needle, green
V = 5356.6 (6) Å30.21 × 0.08 × 0.05 mm
Data collection top
Bruker APEX-II area-detector
diffractometer
6623 independent reflections
Radiation source: fine-focus sealed tube3296 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.088
φ and ω scansθmax = 28.3°, θmin = 1.8°
Absorption correction: multi-scan
(SADABS; Bruker, 2004)
h = 1818
Tmin = 0.824, Tmax = 0.958k = 2929
32478 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)] = 0.050Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.122H-atom parameters constrained
S = 1.04 w = 1/[σ2(Fo2) + (0.035P)2 + 1.0071P]
where P = (Fo2 + 2Fc2)/3
6623 reflections(Δ/σ)max = 0.001
331 parametersΔρmax = 0.39 e Å3
0 restraintsΔρmin = 0.28 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
C210.8356 (4)0.66968 (19)0.4977 (3)0.143 (2)
H210.77720.66850.45180.171*
C220.9284 (6)0.65182 (15)0.4961 (2)0.128 (2)
H220.93200.63870.44920.153*
C231.0158 (4)0.65366 (16)0.5647 (4)0.127 (2)
H231.07790.64170.56360.152*
C241.0104 (3)0.67335 (18)0.6348 (3)0.1247 (18)
H241.06890.67460.68070.150*
C250.9176 (5)0.69121 (15)0.6364 (2)0.1183 (18)
H250.91400.70440.68330.142*
C260.8302 (3)0.68937 (18)0.5678 (4)0.1245 (19)
H260.76820.70130.56890.149*
Cl10.73522 (8)0.78163 (5)0.76685 (6)0.0699 (3)
Cu10.70812 (4)0.54035 (2)0.91408 (3)0.0765 (2)
N60.7157 (2)0.53113 (15)0.80728 (16)0.0653 (8)
N40.6282 (2)0.46387 (14)0.90146 (19)0.0710 (9)
N10.8258 (2)0.55369 (14)1.01541 (16)0.0600 (8)
N20.7640 (2)0.64682 (13)1.04243 (17)0.0699 (9)
H20.77890.67501.07710.084*
N30.6369 (3)0.61669 (14)0.92259 (19)0.0718 (9)
N50.6736 (3)0.42833 (14)0.79915 (19)0.0822 (10)
H50.68650.39530.78020.099*
O10.7120 (3)0.75688 (17)0.8288 (2)0.1517 (15)
O20.7492 (3)0.73481 (18)0.7246 (2)0.1658 (16)
C60.6725 (3)0.65669 (16)0.9798 (2)0.0585 (10)
C50.8365 (3)0.60205 (18)1.0618 (2)0.0591 (10)
C40.9232 (3)0.61012 (19)1.1312 (2)0.0742 (11)
H40.93010.64451.16190.089*
C160.7019 (3)0.47873 (19)0.7699 (2)0.0645 (10)
C150.6287 (3)0.41954 (18)0.8526 (2)0.0646 (10)
C70.6214 (3)0.70970 (17)0.9806 (2)0.0720 (11)
H70.64820.73661.02230.086*
C170.7186 (3)0.4721 (2)0.6998 (3)0.0865 (13)
H170.71070.43480.67510.104*
C10.9007 (3)0.51191 (18)1.0403 (2)0.0743 (11)
H10.89390.47771.00940.089*
C80.5316 (4)0.7222 (2)0.9198 (3)0.1018 (15)
H80.49620.75750.91950.122*
C190.7570 (4)0.5759 (2)0.7053 (3)0.1043 (15)
H190.77480.61000.68410.125*
C30.9972 (3)0.5672 (2)1.1533 (3)0.0915 (14)
H31.05530.57221.19890.110*
C200.7407 (3)0.5788 (2)0.7733 (3)0.0880 (13)
H200.74720.61610.79790.106*
C110.5821 (4)0.4522 (2)0.9519 (3)0.1014 (15)
H110.57990.48280.98580.122*
C140.5863 (3)0.36299 (19)0.8537 (3)0.0820 (12)
H140.58890.33290.81930.098*
C100.5479 (4)0.6300 (2)0.8636 (3)0.1064 (16)
H100.52130.60210.82310.128*
C20.9857 (3)0.5168 (2)1.1080 (3)0.0926 (14)
H2A1.03460.48661.12290.111*
C120.5386 (4)0.3983 (3)0.9560 (3)0.1123 (17)
H120.50770.39230.99180.135*
C130.5415 (4)0.3526 (2)0.9055 (3)0.1029 (15)
H130.51290.31520.90710.124*
C90.4944 (4)0.6811 (3)0.8590 (3)0.1183 (18)
H90.43420.68840.81600.142*
C180.7464 (4)0.5208 (3)0.6689 (3)0.1016 (15)
H180.75840.51700.62280.122*
O30.8213 (2)0.81863 (15)0.7987 (2)0.1434 (14)
O40.6532 (3)0.81604 (17)0.7195 (2)0.1673 (16)
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
C210.134 (6)0.147 (6)0.113 (6)0.051 (5)0.011 (4)0.006 (4)
C220.209 (7)0.094 (4)0.092 (5)0.022 (5)0.071 (5)0.010 (3)
C230.150 (6)0.118 (4)0.151 (5)0.040 (4)0.100 (5)0.029 (4)
C240.117 (5)0.141 (5)0.102 (5)0.010 (4)0.027 (3)0.000 (4)
C250.158 (5)0.117 (4)0.088 (4)0.027 (4)0.056 (5)0.012 (3)
C260.095 (5)0.135 (5)0.154 (5)0.013 (4)0.060 (5)0.042 (5)
Cl10.0773 (8)0.0614 (7)0.0667 (7)0.0069 (6)0.0229 (6)0.0061 (6)
Cu10.0911 (4)0.0667 (3)0.0672 (3)0.0017 (3)0.0256 (3)0.0172 (3)
N60.074 (2)0.057 (2)0.060 (2)0.0060 (17)0.0196 (17)0.0086 (18)
N40.076 (2)0.071 (2)0.070 (2)0.0064 (18)0.0333 (19)0.0166 (19)
N10.066 (2)0.059 (2)0.060 (2)0.0037 (18)0.0297 (17)0.0038 (17)
N20.078 (2)0.061 (2)0.062 (2)0.0066 (19)0.0169 (19)0.0154 (17)
N30.080 (2)0.062 (2)0.059 (2)0.0093 (19)0.0116 (19)0.0065 (18)
N50.123 (3)0.054 (2)0.082 (2)0.001 (2)0.054 (2)0.0144 (19)
O10.207 (4)0.157 (3)0.118 (3)0.061 (3)0.093 (3)0.009 (2)
O20.165 (4)0.155 (3)0.201 (4)0.008 (3)0.097 (3)0.091 (3)
C60.069 (3)0.048 (2)0.060 (3)0.003 (2)0.027 (2)0.002 (2)
C50.066 (3)0.066 (3)0.048 (2)0.002 (2)0.025 (2)0.001 (2)
C40.080 (3)0.090 (3)0.054 (3)0.000 (3)0.027 (2)0.008 (2)
C160.071 (3)0.063 (3)0.058 (3)0.005 (2)0.025 (2)0.002 (2)
C150.061 (3)0.058 (3)0.065 (3)0.004 (2)0.013 (2)0.003 (2)
C70.085 (3)0.052 (3)0.079 (3)0.003 (2)0.031 (3)0.001 (2)
C170.117 (4)0.072 (3)0.078 (3)0.011 (3)0.046 (3)0.007 (3)
C10.081 (3)0.072 (3)0.076 (3)0.013 (3)0.037 (3)0.007 (2)
C80.110 (4)0.073 (3)0.118 (4)0.034 (3)0.039 (4)0.013 (3)
C190.135 (4)0.101 (4)0.093 (4)0.015 (3)0.062 (3)0.013 (3)
C30.076 (3)0.124 (4)0.066 (3)0.015 (3)0.017 (3)0.007 (3)
C200.107 (4)0.070 (3)0.086 (3)0.016 (3)0.036 (3)0.001 (3)
C110.101 (4)0.108 (4)0.117 (4)0.022 (3)0.066 (3)0.028 (3)
C140.088 (3)0.066 (3)0.079 (3)0.010 (3)0.017 (3)0.010 (2)
C100.113 (4)0.095 (4)0.078 (3)0.022 (3)0.000 (3)0.022 (3)
C20.081 (3)0.110 (4)0.077 (3)0.032 (3)0.020 (3)0.000 (3)
C120.098 (4)0.132 (5)0.125 (4)0.029 (4)0.062 (3)0.003 (4)
C130.089 (4)0.094 (4)0.119 (4)0.025 (3)0.032 (3)0.007 (4)
C90.107 (4)0.109 (4)0.108 (4)0.040 (4)0.006 (3)0.006 (4)
C180.123 (4)0.116 (4)0.078 (3)0.008 (3)0.052 (3)0.006 (3)
O30.122 (3)0.120 (3)0.136 (3)0.061 (2)0.009 (2)0.034 (2)
O40.127 (3)0.136 (3)0.175 (4)0.035 (3)0.013 (3)0.021 (3)
Geometric parameters (Å, º) top
C21—C221.3900N5—H50.8600
C21—C261.3900C6—C71.386 (5)
C21—H210.9300C5—C41.405 (5)
C22—C231.3900C4—C31.361 (5)
C22—H220.9300C4—H40.9300
C23—C241.3900C16—C171.404 (5)
C23—H230.9300C15—C141.396 (5)
C24—C251.3900C7—C81.364 (5)
C24—H240.9300C7—H70.9300
C25—C261.3900C17—C181.348 (6)
C25—H250.9300C17—H170.9300
C26—H260.9300C1—C21.365 (5)
Cl1—O21.357 (3)C1—H10.9300
Cl1—O41.387 (3)C8—C91.381 (6)
Cl1—O31.403 (3)C8—H80.9300
Cl1—O11.411 (3)C19—C201.356 (5)
Cu1—N11.990 (3)C19—C181.374 (6)
Cu1—N42.007 (3)C19—H190.9300
Cu1—N32.011 (3)C3—C21.365 (5)
Cu1—N62.016 (3)C3—H30.9300
N6—C161.326 (4)C20—H200.9300
N6—C201.344 (5)C11—C121.364 (6)
N4—C151.333 (4)C11—H110.9300
N4—C111.349 (5)C14—C131.354 (5)
N1—C51.341 (4)C14—H140.9300
N1—C11.354 (4)C10—C91.349 (6)
N2—C51.378 (4)C10—H100.9300
N2—C61.385 (4)C2—H2A0.9300
N2—H20.8600C12—C131.385 (6)
N3—C61.319 (4)C12—H120.9300
N3—C101.347 (5)C13—H130.9300
N5—C161.367 (4)C9—H90.9300
N5—C151.376 (5)C18—H180.9300
C22—C21—C26120.0C3—C4—C5119.4 (4)
C22—C21—H21120.0C3—C4—H4120.3
C26—C21—H21120.0C5—C4—H4120.3
C23—C22—C21120.0N6—C16—N5121.5 (4)
C23—C22—H22120.0N6—C16—C17121.5 (4)
C21—C22—H22120.0N5—C16—C17117.0 (4)
C22—C23—C24120.0N4—C15—N5120.0 (4)
C22—C23—H23120.0N4—C15—C14122.7 (4)
C24—C23—H23120.0N5—C15—C14117.3 (4)
C25—C24—C23120.0C8—C7—C6119.7 (4)
C25—C24—H24120.0C8—C7—H7120.2
C23—C24—H24120.0C6—C7—H7120.2
C26—C25—C24120.0C18—C17—C16118.8 (4)
C26—C25—H25120.0C18—C17—H17120.6
C24—C25—H25120.0C16—C17—H17120.6
C25—C26—C21120.0N1—C1—C2124.1 (4)
C25—C26—H26120.0N1—C1—H1118.0
C21—C26—H26120.0C2—C1—H1118.0
O2—Cl1—O4109.6 (3)C7—C8—C9118.4 (4)
O2—Cl1—O3113.0 (3)C7—C8—H8120.8
O4—Cl1—O3109.2 (2)C9—C8—H8120.8
O2—Cl1—O1107.1 (3)C20—C19—C18117.7 (4)
O4—Cl1—O1108.6 (3)C20—C19—H19121.2
O3—Cl1—O1109.2 (2)C18—C19—H19121.2
N1—Cu1—N4118.04 (12)C4—C3—C2119.6 (4)
N1—Cu1—N394.04 (13)C4—C3—H3120.2
N4—Cu1—N3116.16 (13)C2—C3—H3120.2
N1—Cu1—N6125.76 (12)N6—C20—C19124.0 (4)
N4—Cu1—N692.39 (13)N6—C20—H20118.0
N3—Cu1—N6112.23 (13)C19—C20—H20118.0
C16—N6—C20117.6 (3)N4—C11—C12123.9 (5)
C16—N6—Cu1122.7 (3)N4—C11—H11118.1
C20—N6—Cu1119.6 (3)C12—C11—H11118.1
C15—N4—C11116.8 (4)C13—C14—C15119.1 (4)
C15—N4—Cu1123.5 (3)C13—C14—H14120.5
C11—N4—Cu1119.1 (3)C15—C14—H14120.5
C5—N1—C1116.8 (3)N3—C10—C9124.7 (4)
C5—N1—Cu1124.2 (3)N3—C10—H10117.7
C1—N1—Cu1119.0 (3)C9—C10—H10117.7
C5—N2—C6134.5 (3)C3—C2—C1118.5 (4)
C5—N2—H2112.7C3—C2—H2A120.7
C6—N2—H2112.7C1—C2—H2A120.7
C6—N3—C10116.6 (3)C11—C12—C13118.3 (5)
C6—N3—Cu1125.3 (3)C11—C12—H12120.9
C10—N3—Cu1118.0 (3)C13—C12—H12120.9
C16—N5—C15133.2 (3)C14—C13—C12119.3 (5)
C16—N5—H5113.4C14—C13—H13120.3
C15—N5—H5113.4C12—C13—H13120.3
N3—C6—N2120.4 (3)C10—C9—C8118.2 (5)
N3—C6—C7122.5 (4)C10—C9—H9120.9
N2—C6—C7117.1 (4)C8—C9—H9120.9
N1—C5—N2121.5 (3)C17—C18—C19120.3 (4)
N1—C5—C4121.6 (4)C17—C18—H18119.8
N2—C5—C4116.9 (4)C19—C18—H18119.8
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N2—H2···O1i0.862.263.108 (4)168
N5—H5···O3ii0.862.213.043 (4)163
Symmetry codes: (i) x+3/2, y+3/2, z+2; (ii) x+3/2, y1/2, z+3/2.
 

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