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In the title complex, [CuCl(C4H5N3)(C5H15N3)](ClO4, the CuII ion assumes a distorted square-pyramidal CuN4Cl coordination geometry. Extensive hydrogen bonding occurs, which helps to stabilize the crystal structure.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536806031709/xu2101sup1.cif
Contains datablocks I, global

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536806031709/xu2101Isup2.hkl
Contains datablock I

CCDC reference: 621551

Key indicators

  • Single-crystal X-ray study
  • T = 298 K
  • Mean [sigma](C-C) = 0.015 Å
  • R factor = 0.063
  • wR factor = 0.148
  • Data-to-parameter ratio = 14.1

checkCIF/PLATON results

No syntax errors found



Alert level C STRVA01_ALERT_4_C Flack test results are ambiguous. From the CIF: _refine_ls_abs_structure_Flack 0.430 From the CIF: _refine_ls_abs_structure_Flack_su 0.040 PLAT033_ALERT_2_C Flack Parameter Value Deviates from Zero ....... 0.43 PLAT094_ALERT_2_C Ratio of Maximum / Minimum Residual Density .... 2.45 PLAT232_ALERT_2_C Hirshfeld Test Diff (M-X) Cu1 - Cl1 .. 7.44 su PLAT244_ALERT_4_C Low 'Solvent' Ueq as Compared to Neighbors for Cl2 PLAT341_ALERT_3_C Low Bond Precision on C-C bonds (x 1000) Ang ... 15 PLAT420_ALERT_2_C D-H Without Acceptor N1 - H1A ... ? PLAT420_ALERT_2_C D-H Without Acceptor N3 - H3A ... ?
Alert level G REFLT03_ALERT_4_G Please check that the estimate of the number of Friedel pairs is correct. If it is not, please give the correct count in the _publ_section_exptl_refinement section of the submitted CIF. From the CIF: _diffrn_reflns_theta_max 25.00 From the CIF: _reflns_number_total 2799 Count of symmetry unique reflns 1550 Completeness (_total/calc) 180.58% TEST3: Check Friedels for noncentro structure Estimate of Friedel pairs measured 1249 Fraction of Friedel pairs measured 0.806 Are heavy atom types Z>Si present yes PLAT792_ALERT_1_G Check the Absolute Configuration of N2 = ... S
0 ALERT level A = In general: serious problem 0 ALERT level B = Potentially serious problem 8 ALERT level C = Check and explain 2 ALERT level G = General alerts; check 1 ALERT type 1 CIF construction/syntax error, inconsistent or missing data 5 ALERT type 2 Indicator that the structure model may be wrong or deficient 1 ALERT type 3 Indicator that the structure quality may be low 3 ALERT type 4 Improvement, methodology, query or suggestion 0 ALERT type 5 Informative message, check

Computing details top

Data collection: SMART (Bruker, 2003); cell refinement: SAINT (Bruker, 2003); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997a); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997a); molecular graphics: SHELXTL (Sheldrick, 1997b); software used to prepare material for publication: SHELXTL.

(I) top
Crystal data top
[Cu(C5H15N3)(C4H5N3)Cl](ClO4)F(000) = 844
Mr = 410.75Dx = 1.668 Mg m3
Orthorhombic, Pna21Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2c -2nCell parameters from 3064 reflections
a = 12.019 (2) Åθ = 2.6–25.0°
b = 15.450 (3) ŵ = 1.69 mm1
c = 8.8057 (16) ÅT = 298 K
V = 1635.2 (5) Å3Block, blue
Z = 40.35 × 0.32 × 0.30 mm
Data collection top
Bruker Smart 1000 detector
diffractometer
2799 independent reflections
Radiation source: fine-focus sealed tube2500 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.032
φ and ω scansθmax = 25.0°, θmin = 2.1°
Absorption correction: multi-scan
SADABS (Sheldrick, 2002)
h = 1412
Tmin = 0.540, Tmax = 0.606k = 1818
8212 measured reflectionsl = 910
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)] = 0.063H-atom parameters constrained
wR(F2) = 0.148 w = 1/[σ2(Fo2) + (0.0315P)2 + 11.4496P]
where P = (Fo2 + 2Fc2)/3
S = 1.16(Δ/σ)max = 0.001
2799 reflectionsΔρmax = 1.35 e Å3
199 parametersΔρmin = 0.55 e Å3
1 restraintAbsolute structure: Flack (1983), 1249 Friedel Pairs
Primary atom site location: structure-invariant direct methodsAbsolute structure parameter: 0.43 (4)
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
Cu10.96275 (8)0.77796 (5)0.54819 (12)0.0331 (3)
Cl11.17752 (16)0.77353 (13)0.5213 (3)0.0435 (6)
Cl20.76281 (19)0.36907 (16)0.5178 (3)0.0474 (6)
N10.9712 (8)0.7517 (6)0.7761 (8)0.042 (2)
H1A1.04250.75000.80710.051*
H1B0.93510.79260.82960.051*
N20.9318 (5)0.6496 (4)0.5248 (9)0.0293 (15)
H20.85700.64460.51100.035*
N30.9342 (7)0.7952 (5)0.3300 (8)0.0334 (18)
H3A0.86020.79290.31460.040*
H3B0.95690.84880.30460.040*
N40.9232 (6)0.9070 (4)0.5903 (9)0.0352 (19)
N50.9536 (8)1.0470 (6)0.6929 (13)0.067 (3)
N61.0935 (8)0.9452 (6)0.6888 (13)0.068 (3)
H6A1.11780.89420.66750.082*
H6B1.13690.98230.73110.082*
O10.7677 (7)0.4040 (6)0.6715 (10)0.073 (3)
O20.8536 (10)0.3972 (11)0.4474 (15)0.150 (6)
O30.6622 (8)0.3910 (6)0.4527 (13)0.095 (3)
O40.7679 (11)0.2779 (6)0.527 (2)0.147 (6)
C10.9175 (9)0.6660 (8)0.7975 (11)0.051 (3)
H1C0.93730.64230.89590.061*
H1D0.83730.67180.79290.061*
C20.9566 (10)0.6087 (8)0.6764 (12)0.044 (3)
H2A0.91960.55310.68370.053*
H2B1.03610.59930.68650.053*
C30.9828 (10)0.6023 (7)0.4021 (12)0.043 (3)
H3C0.95960.54220.40540.051*
H3D1.06320.60430.41200.051*
C40.9474 (10)0.6433 (7)0.2509 (11)0.046 (3)
H4A0.97440.60730.16850.055*
H4B0.86680.64350.24570.055*
C50.9880 (10)0.7329 (7)0.2271 (12)0.048 (3)
H5A1.06780.73440.24330.057*
H5B0.97380.74980.12290.057*
C60.9894 (8)0.9664 (6)0.6565 (13)0.044 (2)
C70.8529 (9)1.0674 (6)0.6526 (16)0.064 (4)
H70.82821.12330.67210.076*
C80.7819 (9)1.0115 (6)0.5838 (14)0.058 (3)
H80.71011.02820.55770.070*
C90.8195 (7)0.9300 (5)0.5542 (16)0.049 (2)
H90.77240.89000.50840.059*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Cu10.0368 (5)0.0226 (4)0.0400 (6)0.0005 (4)0.0013 (7)0.0035 (6)
Cl10.0263 (9)0.0404 (11)0.0637 (19)0.0001 (8)0.0022 (11)0.0098 (14)
Cl20.0425 (12)0.0637 (14)0.0359 (13)0.0050 (11)0.0032 (11)0.0019 (12)
N10.051 (6)0.046 (5)0.031 (5)0.005 (4)0.004 (4)0.004 (4)
N20.029 (3)0.026 (3)0.032 (4)0.003 (3)0.000 (3)0.009 (4)
N30.041 (4)0.025 (4)0.034 (4)0.004 (3)0.007 (3)0.004 (3)
N40.036 (4)0.023 (3)0.046 (5)0.002 (3)0.005 (3)0.005 (3)
N50.054 (6)0.037 (5)0.111 (9)0.008 (4)0.024 (6)0.024 (5)
N60.048 (5)0.049 (5)0.107 (9)0.002 (4)0.024 (6)0.031 (6)
O10.052 (5)0.112 (7)0.055 (5)0.014 (5)0.000 (4)0.018 (5)
O20.086 (8)0.269 (18)0.095 (8)0.069 (10)0.034 (7)0.011 (11)
O30.074 (6)0.094 (7)0.117 (8)0.015 (5)0.049 (6)0.013 (6)
O40.193 (12)0.070 (6)0.177 (13)0.037 (7)0.104 (13)0.018 (9)
C10.056 (7)0.069 (8)0.027 (6)0.000 (6)0.004 (5)0.026 (5)
C20.049 (6)0.033 (6)0.051 (6)0.002 (5)0.002 (5)0.000 (5)
C30.054 (7)0.025 (5)0.048 (7)0.009 (5)0.006 (5)0.016 (4)
C40.060 (7)0.050 (6)0.027 (5)0.002 (5)0.004 (5)0.009 (5)
C50.059 (7)0.053 (6)0.032 (5)0.004 (5)0.005 (5)0.006 (5)
C60.038 (5)0.036 (5)0.059 (7)0.003 (4)0.010 (5)0.016 (5)
C70.052 (7)0.030 (5)0.109 (11)0.001 (5)0.032 (7)0.017 (6)
C80.042 (5)0.049 (6)0.083 (10)0.006 (5)0.013 (6)0.001 (6)
C90.034 (4)0.037 (4)0.076 (7)0.002 (4)0.010 (6)0.017 (6)
Geometric parameters (Å, º) top
Cu1—N12.050 (8)N6—C61.325 (13)
Cu1—N22.029 (6)N6—H6A0.8600
Cu1—N31.969 (7)N6—H6B0.8600
Cu1—N42.082 (7)C1—C21.464 (15)
Cu1—Cl12.593 (2)C1—H1C0.9700
Cl2—O11.458 (9)C1—H1D0.9700
Cl2—O21.328 (10)C2—H2A0.9700
Cl2—O31.381 (9)C2—H2B0.9700
Cl2—O41.413 (9)C3—C41.535 (15)
N1—C11.485 (15)C3—H3C0.9700
N1—H1A0.9000C3—H3D0.9700
N1—H1B0.9000C4—C51.482 (15)
N2—C31.440 (12)C4—H4A0.9700
N2—C21.507 (13)C4—H4B0.9700
N2—H20.9100C5—H5A0.9700
N3—C51.473 (12)C5—H5B0.9700
N3—H3A0.9000C7—C81.357 (15)
N3—H3B0.9000C7—H70.9300
N4—C91.335 (11)C8—C91.363 (12)
N4—C61.347 (12)C8—H80.9300
N5—C71.300 (15)C9—H90.9300
N5—C61.357 (12)
N3—Cu1—N290.1 (3)C2—C1—H1C110.1
N3—Cu1—N1172.0 (3)N1—C1—H1C110.1
N2—Cu1—N185.1 (4)C2—C1—H1D110.1
N3—Cu1—N490.2 (3)N1—C1—H1D110.1
N2—Cu1—N4155.8 (2)H1C—C1—H1D108.4
N1—Cu1—N491.5 (3)C1—C2—N2109.2 (8)
N3—Cu1—Cl195.1 (2)C1—C2—H2A109.8
N2—Cu1—Cl198.47 (19)N2—C2—H2A109.8
N1—Cu1—Cl192.0 (3)C1—C2—H2B109.8
N4—Cu1—Cl1105.58 (19)N2—C2—H2B109.8
O2—Cl2—O3116.4 (8)H2A—C2—H2B108.3
O2—Cl2—O4108.5 (10)N2—C3—C4108.9 (8)
O3—Cl2—O4107.9 (6)N2—C3—H3C109.9
O2—Cl2—O1106.2 (7)C4—C3—H3C109.9
O3—Cl2—O1109.3 (6)N2—C3—H3D109.9
O4—Cl2—O1108.3 (8)C4—C3—H3D109.9
C1—N1—Cu1106.2 (6)H3C—C3—H3D108.3
C1—N1—H1A110.5C5—C4—C3114.6 (9)
Cu1—N1—H1A110.5C5—C4—H4A108.6
C1—N1—H1B110.5C3—C4—H4A108.6
Cu1—N1—H1B110.5C5—C4—H4B108.6
H1A—N1—H1B108.7C3—C4—H4B108.6
C3—N2—C2111.6 (6)H4A—C4—H4B107.6
C3—N2—Cu1119.6 (6)N3—C5—C4112.3 (9)
C2—N2—Cu1106.5 (6)N3—C5—H5A109.1
C3—N2—H2106.1C4—C5—H5A109.1
C2—N2—H2106.1N3—C5—H5B109.1
Cu1—N2—H2106.1C4—C5—H5B109.1
C5—N3—Cu1115.8 (6)H5A—C5—H5B107.9
C5—N3—H3A108.3N6—C6—N4118.8 (9)
Cu1—N3—H3A108.3N6—C6—N5118.4 (9)
C5—N3—H3B108.3N4—C6—N5122.7 (9)
Cu1—N3—H3B108.3N5—C7—C8123.6 (10)
H3A—N3—H3B107.4N5—C7—H7118.2
C9—N4—C6118.2 (8)C8—C7—H7118.2
C9—N4—Cu1115.2 (6)C7—C8—C9117.7 (10)
C6—N4—Cu1126.5 (6)C7—C8—H8121.1
C7—N5—C6116.9 (10)C9—C8—H8121.1
C6—N6—H6A120.0N4—C9—C8120.7 (9)
C6—N6—H6B120.0N4—C9—H9119.7
H6A—N6—H6B120.0C8—C9—H9119.7
C2—C1—N1107.9 (8)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N1—H1B···O3i0.902.203.102 (13)177
N2—H2···Cl1ii0.912.503.279 (6)143
N3—H3B···N5iii0.902.173.036 (12)161
N6—H6A···Cl10.862.383.198 (10)160
N6—H6B···O1iv0.862.423.136 (13)142
Symmetry codes: (i) x+3/2, y+1/2, z+1/2; (ii) x1/2, y+3/2, z; (iii) x+2, y+2, z1/2; (iv) x+1/2, y+3/2, z.
 

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