Buy article online - an online subscription or single-article purchase is required to access this article.
Download citation
Download citation
link to html
The title compound, trans-[Cu(gly)2]·4-BrC6H4OH, (I), crystallized in the non-centrosymmetric orthorhombic space group Pca21 when trans-bis­(glycinato-N,O)copper(II) and 4-bromo­phenol were allowed to stand in water for several days. Structural analysis reveals that the 4-bromo­phenol is not coordinated to the copper and that the glycinato units are trans in N,O-bidentate binding mode. The packing of the mol­ecules shows well defined units of (I), interlocked via a network of secondary covalent and non-covalent bonds, with the Cu atom in a [4 + 2] coordination mode.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536804012541/su6106sup1.cif
Contains datablocks global, I

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536804012541/su6106Isup2.hkl
Contains datablock I

CCDC reference: 242289

Key indicators

  • Single-crystal X-ray study
  • T = 293 K
  • Mean [sigma](C-C) = 0.017 Å
  • R factor = 0.043
  • wR factor = 0.104
  • Data-to-parameter ratio = 7.0

checkCIF/PLATON results

No syntax errors found



Alert level B PLAT027_ALERT_3_B _diffrn_reflns_theta_full (too) Low ............ 24.99 Deg. PLAT031_ALERT_4_B Refined Extinction Parameter within Range ...... 1.44 Sigma PLAT341_ALERT_3_B Low Bond Precision on C-C bonds (x 1000) Ang ... 17
Alert level C ABSTM02_ALERT_3_C The ratio of expected to reported Tmax/Tmin(RR) is > 1.10 Tmin and Tmax reported: 0.191 0.308 Tmin and Tmax expected: 0.420 0.757 RR = 1.116 Please check that your absorption correction is appropriate. PLAT029_ALERT_3_C _diffrn_measured_fraction_theta_full Low ....... 0.97 PLAT060_ALERT_3_C Ratio Tmax/Tmin (Exp-to-Rep) (too) Large ....... 1.13 PLAT062_ALERT_4_C Rescale T(min) & T(max) by ..................... 2.46 PLAT089_ALERT_3_C Poor Data / Parameter Ratio (Zmax .LT. 18) ..... 6.98 PLAT242_ALERT_2_C Check Low U(eq) as Compared to Neighbors .... C14 PLAT420_ALERT_2_C D-H Without Acceptor N1 - H1D ... ? PLAT431_ALERT_2_C Short Inter HL..A Contact Br .. O2 .. 3.15 Ang. PLAT480_ALERT_4_C Long H...A H-Bond Reported H1D .. BR .. 3.02 Ang. PLAT710_ALERT_4_C Delete 1-2-3 or 2-3-4 Linear Torsion Angle ... # 1 O1' -CU -O1 -C2 -96.00 3.00 1.555 1.555 1.555 1.555 PLAT710_ALERT_4_C Delete 1-2-3 or 2-3-4 Linear Torsion Angle ... # 6 N1' -CU -N1 -C1 107.00 4.00 1.555 1.555 1.555 1.555 PLAT710_ALERT_4_C Delete 1-2-3 or 2-3-4 Linear Torsion Angle ... # 12 O1 -CU -O1' -C2' -80.00 3.00 1.555 1.555 1.555 1.555 PLAT710_ALERT_4_C Delete 1-2-3 or 2-3-4 Linear Torsion Angle ... # 17 N1 -CU -N1' -C1' 70.00 5.00 1.555 1.555 1.555 1.555 PLAT720_ALERT_4_C Number of Unusual/Non-Standard Label(s) ........ 4
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: C10 H13 Br1 Cu1 N2 O5 Atom count from _chemical_formula_moiety:C10 H14 Br1 Cu1 N2 O5 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 2.457 Tmax scaled 0.757 Tmin scaled 0.469 REFLT03_ALERT_4_G WARNING: Large fraction of Friedel related reflns may be needed to determine absolute structure From the CIF: _diffrn_reflns_theta_max 24.99 From the CIF: _reflns_number_total 1214 Count of symmetry unique reflns 1200 Completeness (_total/calc) 101.17% TEST3: Check Friedels for noncentro structure Estimate of Friedel pairs measured 14 Fraction of Friedel pairs measured 0.012 Are heavy atom types Z>Si present yes
0 ALERT level A = In general: serious problem 3 ALERT level B = Potentially serious problem 14 ALERT level C = Check and explain 3 ALERT level G = General alerts; check 1 ALERT type 1 CIF construction/syntax error, inconsistent or missing data 3 ALERT type 2 Indicator that the structure model may be wrong or deficient 7 ALERT type 3 Indicator that the structure quality may be low 9 ALERT type 4 Improvement, methodology, query or suggestion

Computing details top

Data collection: SHELXTL (Bruker, 1997); cell refinement: SHELXTL; data reduction: SHELXTL; program(s) used to solve structure: SHELXS97 (Sheldrick, 1990) and SIR2002 (Burla et al., 2003); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: SHELXTL, ORTEP-3 (Farrugia, 1997) and PLATON (Spek, 2004); software used to prepare material for publication: SHELXTL and WinGX (Farrugia, 1999).

'trans-bis(glycinato-N,O)copper(II) 4-bromophenol solvate' top
Crystal data top
[Cu(C2H4NO2)2]C6H5BrOF(000) = 764
Mr = 384.67Dx = 1.914 Mg m3
Orthorhombic, Pca21Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2c -2acCell parameters from 61 reflections
a = 9.442 (1) Åθ = 5.8–32.6°
b = 5.063 (1) ŵ = 4.65 mm1
c = 27.926 (4) ÅT = 293 K
V = 1335.0 (4) Å3Prism, blue
Z = 40.26 × 0.16 × 0.06 mm
Data collection top
Bruker P4
diffractometer
983 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tubeRint = 0.045
Graphite monochromatorθmax = 25.0°, θmin = 2.9°
2θ/ω scansh = 111
Absorption correction: empirical
Psi scan (XSCANS; Bruker, 1996)
k = 16
Tmin = 0.191, Tmax = 0.308l = 133
1691 measured reflections3 standard reflections every 97 reflections
1214 independent reflections intensity decay: none
Refinement top
Refinement on F2Hydrogen site location: inferred from neighbouring sites
Least-squares matrix: fullH atoms treated by a mixture of independent and constrained refinement
R[F2 > 2σ(F2)] = 0.043 w = 1/[σ2(Fo2) + (0.0578P)2]
where P = (Fo2 + 2Fc2)/3
wR(F2) = 0.104(Δ/σ)max < 0.001
S = 1.03Δρmax = 0.47 e Å3
1214 reflectionsΔρmin = 0.39 e Å3
174 parametersExtinction correction: SHELXL, Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
1 restraintExtinction coefficient: 0.00013 (9)
Primary atom site location: structure-invariant direct methodsAbsolute structure: Flack H D (1983), Acta Cryst. A39, 876-881
Secondary atom site location: difference Fourier mapAbsolute structure parameter: 0.08 (3)
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
Cu0.36332 (11)0.2586 (2)0.21775 (5)0.0313 (3)
O10.1986 (6)0.4765 (12)0.2029 (2)0.0315 (16)
N10.2868 (9)0.0155 (14)0.1683 (3)0.033 (2)
H1D0.35630.03170.14790.040*
H1C0.25310.13160.18230.040*
C10.1734 (11)0.147 (2)0.1419 (3)0.032 (2)
H1B0.09650.02360.13650.038*
H1A0.20860.20450.11100.038*
C20.1189 (9)0.3840 (19)0.1698 (4)0.030 (2)
O20.0023 (8)0.4820 (15)0.1585 (3)0.0412 (18)
O1'0.5169 (6)0.0229 (12)0.2382 (2)0.0326 (16)
N1'0.4325 (8)0.4846 (15)0.2707 (3)0.0306 (19)
H1'C0.47130.63260.25860.037*
H1'D0.35920.53190.28940.037*
C1'0.5389 (11)0.3430 (18)0.2997 (4)0.037 (2)
H1'A0.49790.29480.33030.044*
H1'B0.61910.45800.30570.044*
C2'0.5891 (11)0.0946 (17)0.2738 (4)0.030 (2)
O2'0.6930 (8)0.0238 (14)0.2894 (3)0.0440 (19)
O30.8525 (9)0.1743 (17)0.3583 (3)0.051 (2)
H30.79270.11130.34030.076*
C110.7951 (12)0.210 (2)0.4027 (4)0.044 (3)
C120.6809 (13)0.063 (2)0.4187 (4)0.049 (3)
H120.63900.06170.39880.058*
C130.6292 (13)0.103 (3)0.4647 (5)0.060 (3)
H130.55310.00400.47590.072*
C140.6910 (12)0.290 (2)0.4937 (4)0.042 (3)
C150.8026 (15)0.431 (3)0.4784 (4)0.058 (3)
H150.84610.55220.49870.070*
C160.8521 (12)0.396 (3)0.4322 (5)0.055 (3)
H160.92590.50060.42110.067*
Br0.61813 (14)0.3465 (3)0.55637 (4)0.0669 (5)
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Cu0.0278 (5)0.0226 (5)0.0435 (7)0.0030 (5)0.0087 (7)0.0058 (5)
O10.025 (3)0.025 (3)0.045 (4)0.007 (3)0.001 (3)0.004 (3)
N10.034 (4)0.024 (4)0.042 (5)0.004 (4)0.013 (4)0.001 (4)
C10.037 (5)0.029 (5)0.030 (5)0.010 (4)0.003 (4)0.004 (4)
C20.018 (4)0.035 (5)0.038 (5)0.010 (5)0.002 (5)0.003 (5)
O20.040 (4)0.045 (5)0.039 (4)0.015 (3)0.007 (4)0.003 (4)
O1'0.031 (3)0.022 (3)0.045 (4)0.003 (3)0.010 (3)0.004 (3)
N1'0.029 (4)0.026 (4)0.036 (4)0.003 (4)0.004 (4)0.008 (3)
C1'0.036 (5)0.030 (5)0.044 (6)0.001 (5)0.004 (5)0.011 (5)
C2'0.037 (5)0.026 (5)0.027 (5)0.002 (5)0.008 (5)0.004 (4)
O2'0.044 (4)0.034 (4)0.054 (5)0.014 (4)0.015 (4)0.004 (4)
O30.061 (5)0.059 (5)0.032 (4)0.022 (4)0.005 (4)0.007 (4)
C110.036 (6)0.045 (7)0.051 (7)0.003 (5)0.007 (5)0.011 (5)
C120.060 (7)0.042 (6)0.044 (7)0.014 (6)0.000 (6)0.004 (5)
C130.049 (7)0.075 (9)0.057 (8)0.013 (7)0.011 (7)0.001 (7)
C140.044 (6)0.054 (7)0.027 (5)0.004 (6)0.005 (5)0.004 (5)
C150.066 (8)0.063 (8)0.046 (7)0.020 (7)0.006 (7)0.011 (6)
C160.053 (7)0.065 (9)0.048 (7)0.020 (7)0.001 (6)0.008 (7)
Br0.0679 (8)0.0927 (10)0.0401 (6)0.0029 (8)0.0025 (8)0.0026 (9)
Geometric parameters (Å, º) top
Cu—O11.951 (6)C1'—H1'A0.9700
Cu—O1'1.963 (6)C1'—H1'B0.9700
Cu—N1'1.981 (8)C2'—O2'1.229 (12)
Cu—N11.986 (8)O3—C111.364 (14)
O1—C21.280 (12)O3—H30.8200
N1—C11.459 (12)C11—C161.361 (16)
N1—H1D0.9000C11—C121.385 (16)
N1—H1C0.9000C12—C131.389 (18)
C1—C21.521 (14)C12—H120.9300
C1—H1B0.9700C13—C141.374 (17)
C1—H1A0.9700C13—H130.9300
C2—O21.249 (12)C14—C151.343 (18)
O1'—C2'1.258 (12)C14—Br1.903 (11)
N1'—C1'1.476 (13)C15—C161.384 (18)
N1'—H1'C0.9000C15—H150.9300
N1'—H1'D0.9000C16—H160.9300
C1'—C2'1.526 (13)
O1—Cu—O1'173.9 (3)N1'—C1'—C2'110.6 (8)
O1—Cu—N1'95.4 (3)N1'—C1'—H1'A109.5
O1'—Cu—N1'83.7 (3)C2'—C1'—H1'A109.5
O1—Cu—N185.0 (3)N1'—C1'—H1'B109.5
O1'—Cu—N195.4 (3)C2'—C1'—H1'B109.5
N1'—Cu—N1175.8 (4)H1'A—C1'—H1'B108.1
C2—O1—Cu114.5 (6)O2'—C2'—O1'124.8 (9)
C1—N1—Cu109.6 (6)O2'—C2'—C1'118.8 (9)
C1—N1—H1D109.8O1'—C2'—C1'116.3 (9)
Cu—N1—H1D109.8C11—O3—H3109.5
C1—N1—H1C109.8C16—C11—O3119.0 (10)
Cu—N1—H1C109.8C16—C11—C12118.8 (12)
H1D—N1—H1C108.2O3—C11—C12122.2 (11)
N1—C1—C2110.5 (8)C11—C12—C13119.7 (11)
N1—C1—H1B109.6C11—C12—H12120.2
C2—C1—H1B109.6C13—C12—H12120.2
N1—C1—H1A109.6C14—C13—C12119.7 (11)
C2—C1—H1A109.6C14—C13—H13120.2
H1B—C1—H1A108.1C12—C13—H13120.2
O2—C2—O1123.8 (9)C15—C14—C13120.9 (11)
O2—C2—C1118.8 (9)C15—C14—Br119.7 (9)
O1—C2—C1117.3 (8)C13—C14—Br119.4 (9)
C2'—O1'—Cu117.1 (6)C14—C15—C16119.4 (11)
C1'—N1'—Cu110.7 (6)C14—C15—H15120.3
C1'—N1'—H1'C109.5C16—C15—H15120.3
Cu—N1'—H1'C109.5C11—C16—C15121.4 (12)
C1'—N1'—H1'D109.5C11—C16—H16119.3
Cu—N1'—H1'D109.5C15—C16—H16119.3
H1'C—N1'—H1'D108.1
O1'—Cu—O1—C296 (3)N1—Cu—N1'—C1'70 (5)
N1'—Cu—O1—C2177.1 (6)Cu—N1'—C1'—C2'13.4 (9)
N1—Cu—O1—C21.4 (6)Cu—O1'—C2'—O2'176.1 (8)
O1—Cu—N1—C111.4 (6)Cu—O1'—C2'—C1'5.9 (10)
O1'—Cu—N1—C1174.8 (6)N1'—C1'—C2'—O2'168.9 (9)
N1'—Cu—N1—C1107 (4)N1'—C1'—C2'—O1'12.9 (12)
Cu—N1—C1—C218.0 (10)C16—C11—C12—C131.5 (18)
Cu—O1—C2—O2173.0 (8)O3—C11—C12—C13178.3 (11)
Cu—O1—C2—C19.2 (11)C11—C12—C13—C141 (2)
N1—C1—C2—O2163.6 (9)C12—C13—C14—C151 (2)
N1—C1—C2—O118.5 (13)C12—C13—C14—Br179.2 (10)
O1—Cu—O1'—C2'80 (3)C13—C14—C15—C163 (2)
N1'—Cu—O1'—C2'1.7 (7)Br—C14—C15—C16177.8 (10)
N1—Cu—O1'—C2'174.1 (7)O3—C11—C16—C15176.8 (12)
O1—Cu—N1'—C1'165.2 (6)C12—C11—C16—C153.0 (19)
O1'—Cu—N1'—C1'8.8 (6)C14—C15—C16—C114 (2)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
O3—H3···O20.821.842.641 (11)166
N1—H1D···Bri0.903.023.732 (9)137
N1—H1C···O1ii0.902.133.013 (10)167
N1—H1C···O1iii0.902.102.980 (10)166
N1—H1D···O3iv0.902.433.088 (11)130
Symmetry codes: (i) x+1, y, z1/2; (ii) x, y1, z; (iii) x, y+1, z; (iv) x1/2, y+1, z.
 

Subscribe to Acta Crystallographica Section E: Crystallographic Communications

The full text of this article is available to subscribers to the journal.

If you have already registered and are using a computer listed in your registration details, please email support@iucr.org for assistance.

Buy online

You may purchase this article in PDF and/or HTML formats. For purchasers in the European Community who do not have a VAT number, VAT will be added at the local rate. Payments to the IUCr are handled by WorldPay, who will accept payment by credit card in several currencies. To purchase the article, please complete the form below (fields marked * are required), and then click on `Continue'.
E-mail address* 
Repeat e-mail address* 
(for error checking) 

Format*   PDF (US $40)
   HTML (US $40)
   PDF+HTML (US $50)
In order for VAT to be shown for your country javascript needs to be enabled.

VAT number 
(non-UK EC countries only) 
Country* 
 

Terms and conditions of use
Contact us

Follow Acta Cryst. E
Sign up for e-alerts
Follow Acta Cryst. on Twitter
Follow us on facebook
Sign up for RSS feeds