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
CCDC reference: 242289
Key indicators
- Single-crystal X-ray study
- T = 293 K
- Mean (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
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]C6H5BrO | F(000) = 764 |
Mr = 384.67 | Dx = 1.914 Mg m−3 |
Orthorhombic, Pca21 | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: P 2c -2ac | Cell parameters from 61 reflections |
a = 9.442 (1) Å | θ = 5.8–32.6° |
b = 5.063 (1) Å | µ = 4.65 mm−1 |
c = 27.926 (4) Å | T = 293 K |
V = 1335.0 (4) Å3 | Prism, blue |
Z = 4 | 0.26 × 0.16 × 0.06 mm |
Data collection top
Bruker P4 diffractometer | 983 reflections with I > 2σ(I) |
Radiation source: fine-focus sealed tube | Rint = 0.045 |
Graphite monochromator | θmax = 25.0°, θmin = 2.9° |
2θ/ω scans | h = −1→11 |
Absorption correction: empirical Psi scan (XSCANS; Bruker, 1996) | k = −1→6 |
Tmin = 0.191, Tmax = 0.308 | l = −1→33 |
1691 measured reflections | 3 standard reflections every 97 reflections |
1214 independent reflections | intensity decay: none |
Refinement top
Refinement on F2 | Hydrogen site location: inferred from neighbouring sites |
Least-squares matrix: full | H 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 = 1.03 | Δρmax = 0.47 e Å−3 |
1214 reflections | Δρmin = −0.39 e Å−3 |
174 parameters | Extinction correction: SHELXL, Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4 |
1 restraint | Extinction coefficient: 0.00013 (9) |
Primary atom site location: structure-invariant direct methods | Absolute structure: Flack H D (1983), Acta Cryst. A39, 876-881 |
Secondary atom site location: difference Fourier map | Absolute 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 | x | y | z | Uiso*/Ueq | |
Cu | 0.36332 (11) | 0.2586 (2) | 0.21775 (5) | 0.0313 (3) | |
O1 | 0.1986 (6) | 0.4765 (12) | 0.2029 (2) | 0.0315 (16) | |
N1 | 0.2868 (9) | 0.0155 (14) | 0.1683 (3) | 0.033 (2) | |
H1D | 0.3563 | −0.0317 | 0.1479 | 0.040* | |
H1C | 0.2531 | −0.1316 | 0.1823 | 0.040* | |
C1 | 0.1734 (11) | 0.147 (2) | 0.1419 (3) | 0.032 (2) | |
H1B | 0.0965 | 0.0236 | 0.1365 | 0.038* | |
H1A | 0.2086 | 0.2045 | 0.1110 | 0.038* | |
C2 | 0.1189 (9) | 0.3840 (19) | 0.1698 (4) | 0.030 (2) | |
O2 | 0.0023 (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'C | 0.4713 | 0.6326 | 0.2586 | 0.037* | |
H1'D | 0.3592 | 0.5319 | 0.2894 | 0.037* | |
C1' | 0.5389 (11) | 0.3430 (18) | 0.2997 (4) | 0.037 (2) | |
H1'A | 0.4979 | 0.2948 | 0.3303 | 0.044* | |
H1'B | 0.6191 | 0.4580 | 0.3057 | 0.044* | |
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) | |
O3 | 0.8525 (9) | 0.1743 (17) | 0.3583 (3) | 0.051 (2) | |
H3 | 0.7927 | 0.1113 | 0.3403 | 0.076* | |
C11 | 0.7951 (12) | 0.210 (2) | 0.4027 (4) | 0.044 (3) | |
C12 | 0.6809 (13) | 0.063 (2) | 0.4187 (4) | 0.049 (3) | |
H12 | 0.6390 | −0.0617 | 0.3988 | 0.058* | |
C13 | 0.6292 (13) | 0.103 (3) | 0.4647 (5) | 0.060 (3) | |
H13 | 0.5531 | 0.0040 | 0.4759 | 0.072* | |
C14 | 0.6910 (12) | 0.290 (2) | 0.4937 (4) | 0.042 (3) | |
C15 | 0.8026 (15) | 0.431 (3) | 0.4784 (4) | 0.058 (3) | |
H15 | 0.8461 | 0.5522 | 0.4987 | 0.070* | |
C16 | 0.8521 (12) | 0.396 (3) | 0.4322 (5) | 0.055 (3) | |
H16 | 0.9259 | 0.5006 | 0.4211 | 0.067* | |
Br | 0.61813 (14) | 0.3465 (3) | 0.55637 (4) | 0.0669 (5) | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
Cu | 0.0278 (5) | 0.0226 (5) | 0.0435 (7) | 0.0030 (5) | −0.0087 (7) | −0.0058 (5) |
O1 | 0.025 (3) | 0.025 (3) | 0.045 (4) | 0.007 (3) | −0.001 (3) | −0.004 (3) |
N1 | 0.034 (4) | 0.024 (4) | 0.042 (5) | 0.004 (4) | 0.013 (4) | 0.001 (4) |
C1 | 0.037 (5) | 0.029 (5) | 0.030 (5) | 0.010 (4) | −0.003 (4) | −0.004 (4) |
C2 | 0.018 (4) | 0.035 (5) | 0.038 (5) | −0.010 (5) | 0.002 (5) | 0.003 (5) |
O2 | 0.040 (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) |
O3 | 0.061 (5) | 0.059 (5) | 0.032 (4) | −0.022 (4) | 0.005 (4) | −0.007 (4) |
C11 | 0.036 (6) | 0.045 (7) | 0.051 (7) | 0.003 (5) | −0.007 (5) | 0.011 (5) |
C12 | 0.060 (7) | 0.042 (6) | 0.044 (7) | −0.014 (6) | 0.000 (6) | −0.004 (5) |
C13 | 0.049 (7) | 0.075 (9) | 0.057 (8) | −0.013 (7) | 0.011 (7) | −0.001 (7) |
C14 | 0.044 (6) | 0.054 (7) | 0.027 (5) | 0.004 (6) | −0.005 (5) | −0.004 (5) |
C15 | 0.066 (8) | 0.063 (8) | 0.046 (7) | −0.020 (7) | −0.006 (7) | −0.011 (6) |
C16 | 0.053 (7) | 0.065 (9) | 0.048 (7) | −0.020 (7) | 0.001 (6) | −0.008 (7) |
Br | 0.0679 (8) | 0.0927 (10) | 0.0401 (6) | 0.0029 (8) | 0.0025 (8) | −0.0026 (9) |
Geometric parameters (Å, º) top
Cu—O1 | 1.951 (6) | C1'—H1'A | 0.9700 |
Cu—O1' | 1.963 (6) | C1'—H1'B | 0.9700 |
Cu—N1' | 1.981 (8) | C2'—O2' | 1.229 (12) |
Cu—N1 | 1.986 (8) | O3—C11 | 1.364 (14) |
O1—C2 | 1.280 (12) | O3—H3 | 0.8200 |
N1—C1 | 1.459 (12) | C11—C16 | 1.361 (16) |
N1—H1D | 0.9000 | C11—C12 | 1.385 (16) |
N1—H1C | 0.9000 | C12—C13 | 1.389 (18) |
C1—C2 | 1.521 (14) | C12—H12 | 0.9300 |
C1—H1B | 0.9700 | C13—C14 | 1.374 (17) |
C1—H1A | 0.9700 | C13—H13 | 0.9300 |
C2—O2 | 1.249 (12) | C14—C15 | 1.343 (18) |
O1'—C2' | 1.258 (12) | C14—Br | 1.903 (11) |
N1'—C1' | 1.476 (13) | C15—C16 | 1.384 (18) |
N1'—H1'C | 0.9000 | C15—H15 | 0.9300 |
N1'—H1'D | 0.9000 | C16—H16 | 0.9300 |
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'A | 109.5 |
O1'—Cu—N1' | 83.7 (3) | C2'—C1'—H1'A | 109.5 |
O1—Cu—N1 | 85.0 (3) | N1'—C1'—H1'B | 109.5 |
O1'—Cu—N1 | 95.4 (3) | C2'—C1'—H1'B | 109.5 |
N1'—Cu—N1 | 175.8 (4) | H1'A—C1'—H1'B | 108.1 |
C2—O1—Cu | 114.5 (6) | O2'—C2'—O1' | 124.8 (9) |
C1—N1—Cu | 109.6 (6) | O2'—C2'—C1' | 118.8 (9) |
C1—N1—H1D | 109.8 | O1'—C2'—C1' | 116.3 (9) |
Cu—N1—H1D | 109.8 | C11—O3—H3 | 109.5 |
C1—N1—H1C | 109.8 | C16—C11—O3 | 119.0 (10) |
Cu—N1—H1C | 109.8 | C16—C11—C12 | 118.8 (12) |
H1D—N1—H1C | 108.2 | O3—C11—C12 | 122.2 (11) |
N1—C1—C2 | 110.5 (8) | C11—C12—C13 | 119.7 (11) |
N1—C1—H1B | 109.6 | C11—C12—H12 | 120.2 |
C2—C1—H1B | 109.6 | C13—C12—H12 | 120.2 |
N1—C1—H1A | 109.6 | C14—C13—C12 | 119.7 (11) |
C2—C1—H1A | 109.6 | C14—C13—H13 | 120.2 |
H1B—C1—H1A | 108.1 | C12—C13—H13 | 120.2 |
O2—C2—O1 | 123.8 (9) | C15—C14—C13 | 120.9 (11) |
O2—C2—C1 | 118.8 (9) | C15—C14—Br | 119.7 (9) |
O1—C2—C1 | 117.3 (8) | C13—C14—Br | 119.4 (9) |
C2'—O1'—Cu | 117.1 (6) | C14—C15—C16 | 119.4 (11) |
C1'—N1'—Cu | 110.7 (6) | C14—C15—H15 | 120.3 |
C1'—N1'—H1'C | 109.5 | C16—C15—H15 | 120.3 |
Cu—N1'—H1'C | 109.5 | C11—C16—C15 | 121.4 (12) |
C1'—N1'—H1'D | 109.5 | C11—C16—H16 | 119.3 |
Cu—N1'—H1'D | 109.5 | C15—C16—H16 | 119.3 |
H1'C—N1'—H1'D | 108.1 | | |
| | | |
O1'—Cu—O1—C2 | −96 (3) | N1—Cu—N1'—C1' | 70 (5) |
N1'—Cu—O1—C2 | −177.1 (6) | Cu—N1'—C1'—C2' | 13.4 (9) |
N1—Cu—O1—C2 | −1.4 (6) | Cu—O1'—C2'—O2' | −176.1 (8) |
O1—Cu—N1—C1 | 11.4 (6) | Cu—O1'—C2'—C1' | 5.9 (10) |
O1'—Cu—N1—C1 | −174.8 (6) | N1'—C1'—C2'—O2' | 168.9 (9) |
N1'—Cu—N1—C1 | 107 (4) | N1'—C1'—C2'—O1' | −12.9 (12) |
Cu—N1—C1—C2 | −18.0 (10) | C16—C11—C12—C13 | −1.5 (18) |
Cu—O1—C2—O2 | 173.0 (8) | O3—C11—C12—C13 | 178.3 (11) |
Cu—O1—C2—C1 | −9.2 (11) | C11—C12—C13—C14 | 1 (2) |
N1—C1—C2—O2 | −163.6 (9) | C12—C13—C14—C15 | −1 (2) |
N1—C1—C2—O1 | 18.5 (13) | C12—C13—C14—Br | 179.2 (10) |
O1—Cu—O1'—C2' | −80 (3) | C13—C14—C15—C16 | 3 (2) |
N1'—Cu—O1'—C2' | 1.7 (7) | Br—C14—C15—C16 | −177.8 (10) |
N1—Cu—O1'—C2' | −174.1 (7) | O3—C11—C16—C15 | −176.8 (12) |
O1—Cu—N1'—C1' | 165.2 (6) | C12—C11—C16—C15 | 3.0 (19) |
O1'—Cu—N1'—C1' | −8.8 (6) | C14—C15—C16—C11 | −4 (2) |
Hydrogen-bond geometry (Å, º) top
D—H···A | D—H | H···A | D···A | D—H···A |
O3—H3···O2′ | 0.82 | 1.84 | 2.641 (11) | 166 |
N1—H1D···Bri | 0.90 | 3.02 | 3.732 (9) | 137 |
N1—H1C···O1ii | 0.90 | 2.13 | 3.013 (10) | 167 |
N1′—H1′C···O1′iii | 0.90 | 2.10 | 2.980 (10) | 166 |
N1′—H1′D···O3iv | 0.90 | 2.43 | 3.088 (11) | 130 |
Symmetry codes: (i) −x+1, −y, z−1/2; (ii) x, y−1, z; (iii) x, y+1, z; (iv) x−1/2, −y+1, z. |