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In the title complex, [CuBr(C14H21N5)]Br, the Cu atom is located at the center of a distorted square pyramid with three N and one Br atoms in the square plane and one N atom at the apex. The Cu atom is displaced by 0.2430 (2) Å from the square plane.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536807019137/dn2154sup1.cif
Contains datablocks global, I

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536807019137/dn2154Isup2.hkl
Contains datablock I

CCDC reference: 647184

Key indicators

  • Single-crystal X-ray study
  • T = 297 K
  • Mean [sigma](C-C) = 0.007 Å
  • R factor = 0.035
  • wR factor = 0.080
  • Data-to-parameter ratio = 19.1

checkCIF/PLATON results

No syntax errors found



Alert level C PLAT062_ALERT_4_C Rescale T(min) & T(max) by ..................... 0.94 PLAT094_ALERT_2_C Ratio of Maximum / Minimum Residual Density .... 2.62 PLAT341_ALERT_3_C Low Bond Precision on C-C bonds (x 1000) Ang ... 7
Alert level G ABSTM02_ALERT_3_G When printed, the submitted absorption T values will be replaced by the scaled T values. Since the ratio of scaled T's is identical to the ratio of reported T values, the scaling does not imply a change to the absorption corrections used in the study. Ratio of Tmax expected/reported 0.941 Tmax scaled 0.558 Tmin scaled 0.366 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 26.99 From the CIF: _reflns_number_total 3796 Count of symmetry unique reflns 2007 Completeness (_total/calc) 189.14% TEST3: Check Friedels for noncentro structure Estimate of Friedel pairs measured 1789 Fraction of Friedel pairs measured 0.891 Are heavy atom types Z>Si present yes PLAT792_ALERT_1_G Check the Absolute Configuration of N2 = ... S PLAT792_ALERT_1_G Check the Absolute Configuration of N3 = ... R
0 ALERT level A = In general: serious problem 0 ALERT level B = Potentially serious problem 3 ALERT level C = Check and explain 4 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: SMART (Bruker, 2001; cell refinement: SAINT (Bruker, 2001); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997); software used to prepare material for publication: PLATON (Spek, 2003).

[(4RS,7SR)-1-(1H-Benzimidazol-2-ylmethyl-κN3)-1,4,7-triazacyclononane- κ3N]bromidocopper(II) bromide top
Crystal data top
[CuBr(C14H21N5)]BrF(000) = 956
Mr = 482.72Dx = 1.835 Mg m3
Orthorhombic, Pna21Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2c -2nCell parameters from 4123 reflections
a = 19.525 (2) Åθ = 2.8–24.2°
b = 7.9390 (9) ŵ = 5.83 mm1
c = 11.2702 (12) ÅT = 297 K
V = 1747.0 (3) Å3Block, colourless
Z = 40.20 × 0.10 × 0.10 mm
Data collection top
Bruker SMART APEX CCD area-detector
diffractometer
3796 independent reflections
Radiation source: fine focus sealed Siemens Mo tube3268 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.036
0.3° wide ω exposures scansθmax = 27.0°, θmin = 2.1°
Absorption correction: multi-scan
(SADABS; Sheldrick, 2001)
h = 2424
Tmin = 0.389, Tmax = 0.593k = 810
12313 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)] = 0.035H-atom parameters constrained
wR(F2) = 0.080 w = 1/[σ2(Fo2) + (0.0378P)2]
where P = (Fo2 + 2Fc2)/3
S = 1.00(Δ/σ)max = 0.001
3796 reflectionsΔρmax = 0.74 e Å3
199 parametersΔρmin = 0.28 e Å3
1 restraintAbsolute structure: Flack (1983), 1789 Friedel pairs measured
Primary atom site location: structure-invariant direct methodsAbsolute structure parameter: 0.017 (12)
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
Cu10.15537 (2)0.08222 (6)0.58863 (4)0.03287 (12)
Br10.14746 (3)0.35578 (6)0.68282 (5)0.06084 (16)
Br20.40028 (2)0.01195 (6)0.77450 (6)0.04833 (13)
C10.2037 (2)0.2360 (6)0.4789 (4)0.0445 (10)
H1A0.22710.21420.40450.053*
H1B0.19280.35510.48170.053*
C20.2506 (2)0.1952 (7)0.5783 (4)0.0512 (12)
H2A0.23200.24200.65100.061*
H2B0.29460.24810.56390.061*
C30.2983 (3)0.0715 (9)0.4959 (5)0.0679 (16)
H3A0.34330.10590.52340.081*
H3B0.30460.00850.43170.081*
C40.2606 (3)0.2218 (8)0.4506 (5)0.0630 (15)
H4A0.26510.31370.50680.076*
H4B0.28050.25760.37590.076*
C50.1723 (3)0.0696 (6)0.3322 (4)0.0475 (12)
H5A0.15490.13500.26600.057*
H5B0.21450.01560.30710.057*
C60.1207 (2)0.0625 (6)0.3661 (4)0.0414 (10)
H6A0.11960.14990.30590.050*
H6B0.07550.01220.37070.050*
C70.0825 (2)0.2343 (6)0.5364 (4)0.0440 (11)
H7A0.03980.20810.49670.053*
H7B0.09120.35400.52750.053*
C80.0774 (2)0.1912 (6)0.6639 (4)0.0363 (10)
C90.0488 (2)0.1931 (6)0.8520 (4)0.0399 (10)
C100.0242 (2)0.2273 (7)0.9662 (4)0.0516 (12)
H100.00200.32250.98180.062*
C110.0401 (2)0.1160 (8)1.0527 (4)0.0560 (14)
H110.02460.13581.12950.067*
C120.0792 (3)0.0283 (8)1.0299 (5)0.0572 (14)
H120.08910.10181.09180.069*
C130.1034 (2)0.0636 (7)0.9179 (5)0.0486 (12)
H130.12880.16030.90290.058*
C140.0883 (2)0.0510 (7)0.8276 (4)0.0369 (10)
N10.13896 (16)0.1372 (5)0.4821 (3)0.0344 (8)
N20.26097 (18)0.0110 (5)0.5943 (4)0.0487 (10)
H20.28090.01190.66550.058*
N30.1865 (2)0.1823 (5)0.4329 (3)0.0436 (9)
H30.16350.28070.42110.052*
N40.10622 (17)0.0531 (5)0.7083 (3)0.0337 (8)
N50.04310 (18)0.2767 (5)0.7470 (3)0.0448 (9)
H50.02110.36920.73610.054*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Cu10.0368 (2)0.0321 (3)0.0297 (3)0.0042 (2)0.0005 (2)0.0004 (2)
Br10.0994 (4)0.0357 (3)0.0474 (3)0.0022 (3)0.0006 (3)0.0071 (2)
Br20.0459 (2)0.0481 (3)0.0509 (3)0.0080 (2)0.0043 (2)0.0023 (2)
C10.048 (3)0.045 (3)0.040 (2)0.013 (2)0.005 (2)0.000 (2)
C20.047 (2)0.063 (3)0.043 (3)0.020 (2)0.000 (2)0.001 (2)
C30.043 (3)0.114 (5)0.047 (3)0.021 (3)0.008 (2)0.001 (3)
C40.071 (3)0.072 (4)0.047 (3)0.033 (3)0.013 (3)0.002 (3)
C50.071 (3)0.045 (3)0.026 (2)0.005 (2)0.009 (2)0.002 (2)
C60.050 (3)0.039 (3)0.035 (2)0.001 (2)0.011 (2)0.000 (2)
C70.049 (3)0.035 (3)0.048 (3)0.010 (2)0.005 (2)0.010 (2)
C80.035 (2)0.037 (2)0.037 (3)0.0019 (18)0.0044 (17)0.002 (2)
C90.030 (2)0.046 (3)0.043 (3)0.0029 (19)0.0003 (19)0.010 (2)
C100.044 (3)0.064 (3)0.047 (3)0.004 (2)0.007 (2)0.013 (3)
C110.046 (3)0.090 (4)0.032 (3)0.007 (3)0.003 (2)0.011 (3)
C120.050 (3)0.087 (4)0.034 (3)0.005 (3)0.005 (2)0.005 (3)
C130.039 (3)0.061 (3)0.045 (3)0.010 (2)0.003 (2)0.004 (2)
C140.024 (2)0.050 (3)0.036 (2)0.0002 (18)0.0008 (17)0.004 (2)
N10.0355 (19)0.036 (2)0.0313 (19)0.0027 (14)0.0005 (15)0.0031 (15)
N20.0324 (18)0.081 (3)0.033 (2)0.0020 (16)0.0021 (17)0.001 (2)
N30.060 (2)0.034 (2)0.036 (2)0.0110 (18)0.0004 (18)0.0041 (16)
N40.0311 (18)0.035 (2)0.035 (2)0.0060 (15)0.0022 (14)0.0032 (16)
N50.045 (2)0.040 (2)0.049 (2)0.0100 (16)0.0095 (17)0.0021 (18)
Geometric parameters (Å, º) top
Cu1—N41.973 (4)C6—H6A0.9700
Cu1—N32.020 (4)C6—H6B0.9700
Cu1—N12.140 (4)C7—N11.478 (6)
Cu1—N22.192 (4)C7—C81.480 (6)
Cu1—Br12.4222 (7)C7—H7A0.9700
C1—C21.482 (7)C7—H7B0.9700
C1—N11.489 (6)C8—N41.331 (6)
C1—H1A0.9700C8—N51.337 (5)
C1—H1B0.9700C9—N51.361 (6)
C2—N21.487 (6)C9—C141.394 (7)
C2—H2A0.9700C9—C101.400 (6)
C2—H2B0.9700C10—C111.352 (7)
C3—N21.480 (6)C10—H100.9300
C3—C41.492 (9)C11—C121.401 (8)
C3—H3A0.9700C11—H110.9300
C3—H3B0.9700C12—C131.376 (8)
C4—N31.494 (6)C12—H120.9300
C4—H4A0.9700C13—C141.397 (7)
C4—H4B0.9700C13—H130.9300
C5—N31.471 (6)C14—N41.390 (5)
C5—C61.504 (7)N2—H20.9100
C5—H5A0.9700N3—H30.9100
C5—H5B0.9700N5—H50.8600
C6—N11.479 (6)
N4—Cu1—N3162.57 (14)N1—C7—H7B109.8
N4—Cu1—N182.38 (15)C8—C7—H7B109.8
N3—Cu1—N182.96 (14)H7A—C7—H7B108.2
N4—Cu1—N2104.71 (15)N4—C8—N5111.5 (4)
N3—Cu1—N282.83 (16)N4—C8—C7121.8 (4)
N1—Cu1—N283.24 (14)N5—C8—C7126.7 (4)
N4—Cu1—Br199.07 (11)N5—C9—C14105.5 (4)
N3—Cu1—Br192.71 (11)N5—C9—C10132.6 (4)
N1—Cu1—Br1165.07 (9)C14—C9—C10121.9 (5)
N2—Cu1—Br1110.49 (11)C11—C10—C9117.2 (5)
C2—C1—N1113.0 (4)C11—C10—H10121.4
C2—C1—H1A109.0C9—C10—H10121.4
N1—C1—H1A109.0C10—C11—C12121.8 (5)
C2—C1—H1B109.0C10—C11—H11119.1
N1—C1—H1B109.0C12—C11—H11119.1
H1A—C1—H1B107.8C13—C12—C11121.5 (5)
C1—C2—N2113.0 (4)C13—C12—H12119.3
C1—C2—H2A109.0C11—C12—H12119.3
N2—C2—H2A109.0C12—C13—C14117.6 (5)
C1—C2—H2B109.0C12—C13—H13121.2
N2—C2—H2B109.0C14—C13—H13121.2
H2A—C2—H2B107.8N4—C14—C9108.7 (4)
N2—C3—C4111.5 (4)N4—C14—C13131.3 (5)
N2—C3—H3A109.3C9—C14—C13120.0 (4)
C4—C3—H3A109.3C7—N1—C6113.3 (3)
N2—C3—H3B109.3C7—N1—C1111.6 (4)
C4—C3—H3B109.3C6—N1—C1113.2 (3)
H3A—C3—H3B108.0C7—N1—Cu1107.7 (3)
C3—C4—N3110.9 (4)C6—N1—Cu1101.9 (3)
C3—C4—H4A109.5C1—N1—Cu1108.4 (3)
N3—C4—H4A109.5C3—N2—C2114.3 (4)
C3—C4—H4B109.5C3—N2—Cu1107.0 (3)
N3—C4—H4B109.5C2—N2—Cu1101.5 (3)
H4A—C4—H4B108.1C3—N2—H2111.2
N3—C5—C6110.7 (4)C2—N2—H2111.2
N3—C5—H5A109.5Cu1—N2—H2111.2
C6—C5—H5A109.5C5—N3—C4114.4 (4)
N3—C5—H5B109.5C5—N3—Cu1112.0 (3)
C6—C5—H5B109.5C4—N3—Cu1104.9 (3)
H5A—C5—H5B108.1C5—N3—H3108.4
N1—C6—C5110.1 (4)C4—N3—H3108.4
N1—C6—H6A109.6Cu1—N3—H3108.4
C5—C6—H6A109.6C8—N4—C14105.5 (4)
N1—C6—H6B109.6C8—N4—Cu1113.4 (3)
C5—C6—H6B109.6C14—N4—Cu1141.0 (4)
H6A—C6—H6B108.2C8—N5—C9108.7 (4)
N1—C7—C8109.4 (4)C8—N5—H5125.6
N1—C7—H7A109.8C9—N5—H5125.6
C8—C7—H7A109.8
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N2—H2···Br20.912.643.395 (4)141
N3—H3···Br2i0.912.643.456 (4)149
N5—H5···Br2ii0.862.583.269 (3)138
Symmetry codes: (i) x+1/2, y1/2, z1/2; (ii) x1/2, y+1/2, z.
 

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