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The structure of the title compound, [Cu(BH4)(C26H20N2)], has been redetermined at 90 K. The geometric parameters of the present structure agree with those previously studied at room temperature [Green, Kennard, Smith, Elcombe, Moore, James & White (1984). Inorg. Chim. Acta, 83, 177-189], but with significantly improved precision.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536806031308/hk2089sup1.cif
Contains datablocks I, global

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536806031308/hk2089Isup2.hkl
Contains datablock I

CCDC reference: 621356

Key indicators

  • Single-crystal X-ray study
  • T = 90 K
  • Mean [sigma](C-C) = 0.002 Å
  • R factor = 0.026
  • wR factor = 0.060
  • Data-to-parameter ratio = 28.0

checkCIF/PLATON results

No syntax errors found



Alert level B PLAT414_ALERT_2_B Short Intra D-H..H-X H1B .. H3B .. 1.82 Ang. PLAT414_ALERT_2_B Short Intra D-H..H-X H1B .. H4B .. 1.80 Ang. PLAT414_ALERT_2_B Short Intra D-H..H-X H2B .. H3B .. 1.80 Ang. PLAT414_ALERT_2_B Short Intra D-H..H-X H2B .. H4B .. 1.83 Ang. PLAT416_ALERT_2_B Short Intra D-H..H-D H1B .. H2B .. 1.82 Ang.
Alert level C PLAT066_ALERT_1_C Predicted and Reported Transmissions Identical . ? PLAT094_ALERT_2_C Ratio of Maximum / Minimum Residual Density .... 2.29 PLAT230_ALERT_2_C Hirshfeld Test Diff for N2 - C6 .. 5.21 su PLAT701_ALERT_1_C Bond Calc 1.4770(19), Rep 1.479(2), Dev.. 1.05 Sigma C3 -C13 1.555 1.555 PLAT731_ALERT_1_C Bond Calc 1.4035(18), Rep 1.404(4) ...... 2.22 su-Ra C4 -C5 1.555 1.555
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 33.00 From the CIF: _reflns_number_total 7938 Count of symmetry unique reflns 4028 Completeness (_total/calc) 197.07% TEST3: Check Friedels for noncentro structure Estimate of Friedel pairs measured 3910 Fraction of Friedel pairs measured 0.971 Are heavy atom types Z>Si present yes
0 ALERT level A = In general: serious problem 5 ALERT level B = Potentially serious problem 5 ALERT level C = Check and explain 1 ALERT level G = General alerts; check 3 ALERT type 1 CIF construction/syntax error, inconsistent or missing data 7 ALERT type 2 Indicator that the structure model may be wrong or deficient 0 ALERT type 3 Indicator that the structure quality may be low 1 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: SAINT-Plus (Bruker, 2004); program(s) used to solve structure: XS in SHELXTL (Sheldrick, 2000); program(s) used to refine structure: XL in SHELXTL; molecular graphics: XP in SHELXTL; software used to prepare material for publication: enCIFer (Allen et al., 2004).

(2,9-Dimethyl-4,7-diphenyl-1,10-phenanthroline)(tetrahydroborato)copper(I) top
Crystal data top
[Cu(BH4)(C26H20N2)]F(000) = 912
Mr = 438.82Dx = 1.366 Mg m3
Monoclinic, CcMo Kα radiation, λ = 0.71073 Å
Hall symbol: C -2ycCell parameters from 8024 reflections
a = 14.6291 (5) Åθ = 2.9–31.4°
b = 19.9859 (7) ŵ = 1.04 mm1
c = 7.5743 (3) ÅT = 90 K
β = 105.529 (1)°Block, orange–red
V = 2133.70 (13) Å30.10 × 0.04 × 0.03 mm
Z = 4
Data collection top
Bruker SMART APEX2
diffractometer
7938 independent reflections
Radiation source: rotating anode7219 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.031
ω scansθmax = 33.0°, θmin = 1.8°
Absorption correction: multi-scan
(SADABS; Sheldrick, 1996)
h = 2222
Tmin = 0.903, Tmax = 0.970k = 3030
21394 measured reflectionsl = 1111
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)] = 0.026H atoms treated by a mixture of independent and constrained refinement
wR(F2) = 0.060 w = 1/[σ2(Fo2) + (0.0227P)2]
where P = (Fo2 + 2Fc2)/3
S = 1.01(Δ/σ)max = 0.001
7938 reflectionsΔρmax = 0.64 e Å3
284 parametersΔρmin = 0.28 e Å3
8 restraintsAbsolute structure: Flack (1983), 3922 Friedel pairs
Primary atom site location: structure-invariant direct methodsAbsolute structure parameter: 0.027 (5)
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*/UeqOcc. (<1)
Cu10.115069 (14)0.095239 (7)0.587008 (19)0.01696 (4)
B10.22900 (10)0.16299 (8)0.6784 (2)0.0201 (3)
N10.02374 (8)0.09613 (5)0.44651 (15)0.01508 (19)
N20.09261 (7)0.00548 (5)0.56881 (15)0.0151 (2)
C10.07998 (9)0.14917 (6)0.39231 (17)0.0166 (2)
C20.17441 (9)0.14132 (6)0.28953 (17)0.0163 (2)
H20.21330.17980.25670.020*
C30.21257 (9)0.07877 (6)0.23445 (17)0.0146 (2)
C40.15234 (9)0.02188 (6)0.28950 (16)0.0139 (2)
C50.05986 (9)0.03386 (6)0.39829 (17)0.0139 (2)
C60.00334 (9)0.02183 (6)0.46691 (17)0.0144 (2)
C70.02816 (8)0.08797 (6)0.42644 (17)0.0142 (2)
C80.03606 (9)0.14049 (6)0.50509 (17)0.0152 (2)
C90.12502 (10)0.12230 (6)0.61119 (18)0.0175 (2)
H90.16850.15620.66790.021*
C100.15274 (9)0.05472 (6)0.63725 (17)0.0171 (2)
C110.12007 (9)0.09781 (6)0.30263 (17)0.0154 (2)
H110.14040.14200.26540.018*
C120.17912 (8)0.04557 (6)0.23682 (17)0.0154 (2)
H120.23940.05410.15420.019*
C130.31265 (9)0.07424 (6)0.12617 (17)0.0158 (2)
C140.37657 (9)0.02920 (6)0.16879 (17)0.0178 (2)
H140.35480.00240.26440.021*
C150.47197 (9)0.03039 (7)0.0721 (2)0.0223 (3)
H150.51470.00080.10140.027*
C160.50495 (11)0.07637 (8)0.0657 (2)0.0247 (3)
H160.57040.07740.12950.030*
C170.44208 (10)0.12141 (7)0.11162 (19)0.0229 (3)
H170.46450.15260.20820.028*
C180.34738 (10)0.12058 (6)0.01659 (18)0.0196 (2)
H180.30500.15160.04770.024*
C190.03961 (10)0.21708 (7)0.45052 (19)0.0216 (3)
H19A0.02690.21260.52080.032*0.40 (2)
H19B0.07580.23830.52700.032*0.40 (2)
H19C0.04350.24470.34180.032*0.40 (2)
H19D0.08850.25110.40560.032*0.60 (2)
H19E0.01420.22550.39940.032*0.60 (2)
H19F0.01810.21910.58460.032*0.60 (2)
H2B0.1796 (11)0.1390 (9)0.761 (2)0.032*
H1B0.2028 (12)0.1378 (9)0.5361 (19)0.032*
H3B0.2990 (10)0.1480 (9)0.743 (2)0.032*
H4B0.2165 (13)0.2147 (7)0.664 (2)0.032*
C200.01344 (9)0.21242 (6)0.47198 (17)0.0156 (2)
C210.07430 (9)0.24000 (6)0.47451 (17)0.0177 (2)
H210.12090.21230.50370.021*
C220.09419 (10)0.30708 (7)0.43508 (18)0.0205 (2)
H220.15420.32480.43630.025*
C230.02624 (10)0.34825 (7)0.39379 (19)0.0224 (3)
H230.04010.39400.36450.027*
C240.06225 (10)0.32225 (6)0.39549 (19)0.0214 (2)
H240.10920.35060.36980.026*
C250.08213 (9)0.25507 (6)0.43468 (18)0.0190 (2)
H250.14290.23780.43620.023*
C260.25161 (10)0.03644 (8)0.7403 (2)0.0232 (3)
H26A0.25770.01240.74750.035*
H26B0.29630.05460.67680.035*
H26C0.26570.05510.86430.035*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Cu10.01498 (6)0.01594 (6)0.01946 (7)0.00355 (7)0.00374 (5)0.00136 (7)
B10.0143 (6)0.0202 (7)0.0254 (7)0.0037 (5)0.0043 (5)0.0045 (6)
N10.0160 (5)0.0131 (4)0.0161 (5)0.0009 (4)0.0042 (4)0.0003 (3)
N20.0118 (5)0.0152 (4)0.0177 (5)0.0004 (3)0.0026 (4)0.0005 (4)
C10.0178 (6)0.0145 (5)0.0171 (6)0.0009 (4)0.0043 (4)0.0010 (4)
C20.0180 (6)0.0137 (5)0.0165 (5)0.0020 (4)0.0030 (4)0.0022 (4)
C30.0162 (6)0.0135 (5)0.0138 (5)0.0010 (4)0.0031 (4)0.0020 (4)
C40.0147 (5)0.0124 (5)0.0143 (5)0.0002 (4)0.0037 (4)0.0000 (4)
C50.0139 (5)0.0132 (5)0.0147 (5)0.0002 (4)0.0041 (4)0.0004 (4)
C60.0151 (6)0.0138 (5)0.0151 (5)0.0004 (4)0.0052 (4)0.0004 (4)
C70.0138 (5)0.0139 (5)0.0151 (5)0.0012 (4)0.0041 (4)0.0002 (4)
C80.0158 (5)0.0136 (5)0.0165 (5)0.0023 (4)0.0052 (4)0.0001 (4)
C90.0175 (7)0.0150 (5)0.0196 (7)0.0013 (5)0.0042 (5)0.0005 (5)
C100.0143 (5)0.0175 (6)0.0187 (6)0.0007 (4)0.0032 (4)0.0019 (4)
C110.0165 (5)0.0139 (5)0.0153 (5)0.0012 (4)0.0035 (4)0.0023 (4)
C120.0136 (5)0.0148 (5)0.0169 (5)0.0000 (4)0.0023 (4)0.0012 (4)
C130.0166 (5)0.0139 (5)0.0155 (5)0.0021 (4)0.0017 (4)0.0015 (4)
C140.0161 (5)0.0163 (5)0.0198 (6)0.0021 (4)0.0025 (4)0.0004 (4)
C150.0173 (6)0.0198 (6)0.0282 (7)0.0004 (5)0.0034 (5)0.0054 (5)
C160.0162 (6)0.0253 (6)0.0283 (7)0.0040 (5)0.0013 (5)0.0057 (5)
C170.0243 (6)0.0202 (6)0.0205 (6)0.0081 (5)0.0007 (5)0.0010 (5)
C180.0231 (6)0.0154 (5)0.0183 (6)0.0036 (5)0.0020 (5)0.0005 (4)
C190.0243 (7)0.0115 (5)0.0255 (7)0.0032 (5)0.0004 (5)0.0002 (5)
C200.0161 (5)0.0148 (5)0.0151 (5)0.0008 (4)0.0028 (4)0.0002 (4)
C210.0178 (6)0.0183 (5)0.0175 (6)0.0012 (4)0.0055 (4)0.0011 (4)
C220.0214 (6)0.0185 (6)0.0214 (6)0.0026 (5)0.0053 (5)0.0005 (5)
C230.0281 (7)0.0162 (6)0.0231 (6)0.0009 (5)0.0075 (5)0.0010 (5)
C240.0240 (6)0.0155 (5)0.0271 (6)0.0029 (5)0.0108 (5)0.0005 (5)
C250.0189 (6)0.0162 (5)0.0234 (6)0.0030 (4)0.0082 (5)0.0016 (4)
C260.0144 (6)0.0221 (7)0.0296 (7)0.0020 (5)0.0002 (5)0.0018 (5)
Geometric parameters (Å, º) top
Cu1—N12.025 (1)C8—C91.383 (2)
Cu1—N22.038 (1)C8—C201.481 (2)
Cu1—B12.115 (1)C9—C101.409 (2)
Cu1—H2B1.65 (2)C9—H90.9500
Cu1—H1B1.67 (2)C10—C261.493 (2)
B1—H2B1.18 (1)C11—C121.362 (2)
B1—H1B1.16 (1)C11—H110.9500
B1—H3B1.05 (1)C12—H120.9500
B1—H4B1.05 (1)C13—C141.397 (2)
N1—C11.337 (2)C13—C181.411 (2)
N1—C51.363 (2)C14—C151.392 (2)
N2—C101.329 (2)C14—H140.9500
N2—C61.367 (2)C15—C161.377 (2)
C23—C221.389 (2)C15—H150.9500
C23—C241.392 (2)C16—C171.396 (2)
C23—H230.9500C16—H160.9500
C24—C251.389 (2)C17—C181.380 (2)
C24—H240.9500C17—H170.9500
C25—C201.403 (2)C18—H180.9500
C25—H250.9500C19—H19A0.9800
C1—C21.401 (2)C19—H19B0.9800
C1—C191.499 (2)C19—H19C0.9800
C2—C31.387 (2)C19—H19D0.9800
C2—H20.9500C19—H19E0.9800
C3—C41.431 (2)C19—H19F0.9800
C3—C131.479 (2)C20—C211.402 (2)
C4—C51.404 (4)C21—C221.387 (2)
C4—C121.431 (2)C21—H210.9500
C5—C61.451 (2)C22—H220.9500
C6—C71.406 (2)C26—H26A0.9800
C7—C81.428 (2)C26—H26B0.9800
C7—C111.432 (2)C26—H26C0.9800
N1—Cu1—N281.51 (4)N2—C10—C26118.03 (12)
N1—Cu1—B1139.29 (5)C9—C10—C26120.66 (12)
N2—Cu1—B1138.86 (5)C12—C11—C7121.78 (11)
N1—Cu1—H2B133.9 (6)C12—C11—H11119.1
N2—Cu1—H2B128.7 (6)C7—C11—H11119.1
B1—Cu1—H2B33.6 (5)C11—C12—C4121.40 (11)
N1—Cu1—H1B126.8 (5)C11—C12—H12119.3
N2—Cu1—H1B127.4 (6)C4—C12—H12119.3
B1—Cu1—H1B33.1 (5)C14—C13—C18118.31 (12)
H2B—Cu1—H1B66.6 (6)C14—C13—C3122.45 (11)
Cu1—B1—H2B50.9 (8)C18—C13—C3119.04 (12)
Cu1—B1—H1B51.8 (8)C15—C14—C13120.42 (12)
H2B—B1—H1B102.6 (11)C15—C14—H14119.8
Cu1—B1—H3B123.5 (10)C13—C14—H14119.8
H2B—B1—H3B107.3 (11)C16—C15—C14120.58 (13)
H1B—B1—H3B110.3 (12)C16—C15—H15119.7
Cu1—B1—H4B119.7 (10)C14—C15—H15119.7
H2B—B1—H4B110.1 (12)C15—C16—C17119.89 (13)
H1B—B1—H4B109.0 (12)C15—C16—H16120.1
H3B—B1—H4B116.7 (13)C17—C16—H16120.1
C1—N1—C5118.62 (12)C18—C17—C16119.93 (13)
C1—N1—Cu1128.05 (9)C18—C17—H17120.0
C5—N1—Cu1113.27 (8)C16—C17—H17120.0
C10—N2—C6118.41 (11)C17—C18—C13120.86 (13)
C10—N2—Cu1128.82 (9)C17—C18—H18119.6
C6—N2—Cu1112.74 (8)C13—C18—H18119.6
C22—C23—C24119.78 (12)C1—C19—H19A109.5
C22—C23—H23120.1C1—C19—H19B109.5
C24—C23—H23120.1H19A—C19—H19B109.5
C25—C24—C23120.26 (12)C1—C19—H19C109.5
C25—C24—H24119.9H19A—C19—H19C109.5
C23—C24—H24119.9H19B—C19—H19C109.5
C24—C25—C20120.67 (12)C1—C19—H19D109.4
C24—C25—H25119.7H19A—C19—H19D141.1
C20—C25—H25119.7H19B—C19—H19D56.3
N1—C1—C2121.06 (12)H19C—C19—H19D56.2
N1—C1—C19117.77 (11)C1—C19—H19E109.5
C2—C1—C19121.14 (11)H19A—C19—H19E56.3
C3—C2—C1121.70 (11)H19B—C19—H19E141.1
C3—C2—H2119.1H19C—C19—H19E56.2
C1—C2—H2119.1H19D—C19—H19E109.5
C2—C3—C4117.50 (11)C1—C19—H19F109.5
C2—C3—C13118.79 (11)H19A—C19—H19F56.3
C4—C3—C13123.70 (11)H19B—C19—H19F56.2
C5—C4—C12118.27 (11)H19C—C19—H19F141.0
C5—C4—C3117.21 (11)H19D—C19—H19F109.5
C12—C4—C3124.50 (11)H19E—C19—H19F109.5
N1—C5—C4123.83 (11)C21—C20—C25118.15 (11)
N1—C5—C6116.11 (11)C21—C20—C8122.90 (11)
C4—C5—C6120.06 (11)C25—C20—C8118.95 (11)
N2—C6—C7123.74 (11)C22—C21—C20121.14 (12)
N2—C6—C5116.08 (11)C22—C21—H21119.4
C7—C6—C5120.17 (11)C20—C21—H21119.4
C6—C7—C8117.35 (11)C21—C22—C23119.96 (12)
C6—C7—C11117.86 (10)C21—C22—H22120.0
C8—C7—C11124.72 (11)C23—C22—H22120.0
C9—C8—C7117.43 (11)C10—C26—H26A109.5
C9—C8—C20119.11 (10)C10—C26—H26B109.5
C7—C8—C20123.40 (11)H26A—C26—H26B109.5
C8—C9—C10121.63 (11)C10—C26—H26C109.5
C8—C9—H9119.2H26A—C26—H26C109.5
C10—C9—H9119.2H26B—C26—H26C109.5
N2—C10—C9121.30 (12)
N2—Cu1—N1—C1177.97 (11)C5—C6—C7—C115.84 (17)
B1—Cu1—N1—C18.37 (15)C6—C7—C8—C91.56 (17)
N2—Cu1—N1—C54.85 (9)C11—C7—C8—C9175.18 (12)
B1—Cu1—N1—C5168.81 (9)C6—C7—C8—C20178.84 (11)
N1—Cu1—N2—C10177.82 (12)C11—C7—C8—C202.10 (19)
B1—Cu1—N2—C108.46 (16)C7—C8—C9—C101.7 (2)
N1—Cu1—N2—C64.10 (9)C20—C8—C9—C10175.68 (12)
B1—Cu1—N2—C6169.62 (9)C6—N2—C10—C91.98 (18)
C22—C23—C24—C251.3 (2)Cu1—N2—C10—C9179.97 (10)
C23—C24—C25—C200.4 (2)C6—N2—C10—C26176.95 (12)
C5—N1—C1—C20.59 (19)Cu1—N2—C10—C261.04 (17)
Cu1—N1—C1—C2177.64 (9)C8—C9—C10—N23.7 (2)
C5—N1—C1—C19178.58 (11)C8—C9—C10—C26175.24 (13)
Cu1—N1—C1—C194.38 (17)C6—C7—C11—C125.33 (18)
N1—C1—C2—C32.23 (19)C8—C7—C11—C12177.94 (12)
C19—C1—C2—C3179.86 (12)C7—C11—C12—C40.47 (19)
C1—C2—C3—C41.18 (18)C5—C4—C12—C115.69 (18)
C1—C2—C3—C13179.92 (12)C3—C4—C12—C11176.25 (12)
C2—C3—C4—C51.30 (17)C2—C3—C13—C14131.86 (13)
C13—C3—C4—C5177.54 (12)C4—C3—C13—C1446.97 (18)
C2—C3—C4—C12176.78 (11)C2—C3—C13—C1842.88 (17)
C13—C3—C4—C124.38 (19)C4—C3—C13—C18138.30 (13)
C1—N1—C5—C42.08 (19)C18—C13—C14—C150.02 (18)
Cu1—N1—C5—C4175.39 (10)C3—C13—C14—C15174.79 (12)
C1—N1—C5—C6177.73 (11)C13—C14—C15—C160.7 (2)
Cu1—N1—C5—C64.81 (14)C14—C15—C16—C171.2 (2)
C12—C4—C5—N1175.18 (12)C15—C16—C17—C181.2 (2)
C3—C4—C5—N13.02 (18)C16—C17—C18—C130.6 (2)
C12—C4—C5—C65.02 (17)C14—C13—C18—C170.02 (19)
C3—C4—C5—C6176.78 (11)C3—C13—C18—C17174.93 (12)
C10—N2—C6—C71.52 (18)C24—C25—C20—C212.08 (19)
Cu1—N2—C6—C7176.78 (10)C24—C25—C20—C8177.34 (12)
C10—N2—C6—C5178.96 (11)C9—C8—C20—C21139.05 (14)
Cu1—N2—C6—C52.74 (14)C7—C8—C20—C2143.71 (18)
N1—C5—C6—N21.37 (16)C9—C8—C20—C2541.55 (17)
C4—C5—C6—N2178.82 (11)C7—C8—C20—C25135.69 (13)
N1—C5—C6—C7179.09 (11)C25—C20—C21—C222.19 (18)
C4—C5—C6—C70.73 (18)C8—C20—C21—C22177.21 (12)
N2—C6—C7—C83.30 (18)C20—C21—C22—C230.6 (2)
C5—C6—C7—C8177.19 (11)C24—C23—C22—C211.2 (2)
N2—C6—C7—C11173.67 (12)
 

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