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In the title complex, [Cu(L)(phen)]·2H2O, {LH2 = 3-[(E)-(5-bromo-2-oxidophen­yl)methyl­eneamino]propanoic acid (C10H10BrNO3) and phen = 1,10-phenanthroline (C12H8N2)}, the CuII atom is coordinated in a slightly distorted square-pyramidal geometry by two O atoms and one N atom from an L2− ligand, and two N atoms from a phen ligand. One of the carboxyl­ate O atoms is in the apical position. In the crystal structure, a two-dimensional supra­molecular network is formed through inter­molecular N—H...O and O—H...O hydrogen bonds.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536806052500/lh2236sup1.cif
Contains datablocks I, global

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536806052500/lh2236Isup2.hkl
Contains datablock I

CCDC reference: 633910

Key indicators

  • Single-crystal X-ray study
  • T = 293 K
  • Mean [sigma](C-C) = 0.014 Å
  • R factor = 0.057
  • wR factor = 0.122
  • Data-to-parameter ratio = 11.7

checkCIF/PLATON results

No syntax errors found



Alert level B PLAT245_ALERT_2_B U(iso) H2WA Smaller than U(eq) O2W by ... 0.06 AngSq
Alert level C PLAT128_ALERT_4_C Non-standard setting of Space group Pc .... Pn PLAT220_ALERT_2_C Large Non-Solvent O Ueq(max)/Ueq(min) ... 2.72 Ratio PLAT223_ALERT_4_C Large Solvent/Anion H Ueq(max)/Ueq(min) ... 4.00 Ratio PLAT242_ALERT_2_C Check Low Ueq as Compared to Neighbors for C10 PLAT341_ALERT_3_C Low Bond Precision on C-C bonds (x 1000) Ang ... 14 PLAT353_ALERT_3_C Long N-H Bond (0.87A) N1 - H1A ... 1.02 Ang. PLAT720_ALERT_4_C Number of Unusual/Non-Standard Label(s) ........ 4 PLAT850_ALERT_2_C Check Flack Parameter Exact Value 0.00 and su .. 0.01
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 25.99 From the CIF: _reflns_number_total 3605 Count of symmetry unique reflns 2156 Completeness (_total/calc) 167.21% TEST3: Check Friedels for noncentro structure Estimate of Friedel pairs measured 1449 Fraction of Friedel pairs measured 0.672 Are heavy atom types Z>Si present yes PLAT199_ALERT_1_G Check the Reported _cell_measurement_temperature 293 K PLAT200_ALERT_1_G Check the Reported _diffrn_ambient_temperature . 293 K PLAT792_ALERT_1_G Check the Absolute Configuration of N1 = ... R
0 ALERT level A = In general: serious problem 1 ALERT level B = Potentially serious problem 8 ALERT level C = Check and explain 4 ALERT level G = General alerts; check 3 ALERT type 1 CIF construction/syntax error, inconsistent or missing data 4 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 4 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: PLATON (Spek, 2003); software used to prepare material for publication: SHELXTL (Bruker, 2001).

{3-[(E)-(5-Bromo-2-oxidophenyl)methyleneamino]propanoato-k3O,N,O'}(1,10- phenanthroline-k2N,N')copper(II) dihydrate top
Crystal data top
[Cu(C10H10BrNO3)(C12H8N2)]·2H2OF(000) = 558
Mr = 551.88Dx = 1.668 Mg m3
Monoclinic, PnMo Kα radiation, λ = 0.71073 Å
Hall symbol: P -2yacCell parameters from 2006 reflections
a = 11.120 (2) Åθ = 2.1–26.0°
b = 5.3808 (11) ŵ = 2.85 mm1
c = 18.393 (4) ÅT = 293 K
β = 93.47 (3)°Prism, blue
V = 1098.5 (4) Å30.18 × 0.08 × 0.06 mm
Z = 2
Data collection top
Bruker SMART CCD
diffractometer
3605 independent reflections
Radiation source: fine-focus sealed tube2695 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.039
φ and ω scansθmax = 26.0°, θmin = 2.1°
Absorption correction: multi-scan
(SADABS; Sheldrick, 1996)
h = 1313
Tmin = 0.628, Tmax = 0.848k = 65
5630 measured reflectionsl = 2122
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)] = 0.057H atoms treated by a mixture of independent and constrained refinement
wR(F2) = 0.122 w = 1/[σ2(Fo2) + (0.0239P)2 + 4.2874P]
where P = (Fo2 + 2Fc2)/3
S = 0.97(Δ/σ)max = 0.007
3605 reflectionsΔρmax = 0.77 e Å3
309 parametersΔρmin = 0.62 e Å3
8 restraintsAbsolute structure: Flack (1983), 1462 Friedel pairs
Primary atom site location: structure-invariant direct methodsAbsolute structure parameter: 0.00 (1)
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
Br11.11996 (9)0.3852 (2)0.34870 (6)0.0714 (4)
C10.7947 (8)0.5843 (16)0.1871 (5)0.036 (2)
C20.8970 (8)0.7341 (17)0.1929 (5)0.044 (2)
H20.90140.87180.16260.053*
C30.9915 (9)0.6836 (19)0.2422 (6)0.049 (3)
H31.05770.78930.24630.059*
C40.9877 (9)0.4756 (18)0.2855 (5)0.044 (2)
C50.8878 (8)0.3213 (18)0.2805 (5)0.041 (2)
H50.88590.18140.31000.049*
C60.7917 (8)0.3724 (15)0.2324 (5)0.035 (2)
C70.6846 (8)0.2011 (16)0.2260 (5)0.037 (2)
H7A0.68280.11700.17930.044*
H7B0.69280.07580.26380.044*
C80.5669 (9)0.454 (2)0.3050 (5)0.050 (2)
H8A0.62950.57940.30960.060*
H8B0.58520.32830.34180.060*
C90.4473 (9)0.5731 (17)0.3192 (5)0.047 (2)
H9A0.38310.45940.30370.056*
H9B0.44340.59840.37120.056*
C100.4257 (9)0.8166 (17)0.2813 (5)0.047 (2)
C110.2886 (9)0.2955 (18)0.1533 (5)0.045 (2)
H110.32360.18700.18780.054*
C120.1653 (9)0.276 (2)0.1343 (6)0.056 (3)
H120.11970.15660.15670.067*
C130.1111 (9)0.430 (2)0.0832 (5)0.055 (3)
H130.02900.41800.07060.066*
C140.1827 (8)0.6092 (18)0.0498 (5)0.047 (2)
C150.1352 (9)0.781 (2)0.0034 (5)0.054 (3)
H150.05340.77820.01730.065*
C160.2079 (10)0.949 (2)0.0339 (5)0.055 (3)
H160.17541.05690.06940.066*
C170.3329 (9)0.9639 (18)0.0125 (5)0.043 (2)
C180.4120 (11)1.1323 (17)0.0412 (5)0.054 (3)
H180.38421.24520.07660.065*
C190.5297 (10)1.1319 (19)0.0175 (5)0.058 (3)
H190.58311.24330.03690.069*
C200.5702 (9)0.9635 (17)0.0361 (5)0.043 (2)
H200.65090.96680.05250.052*
C210.3805 (8)0.8007 (16)0.0397 (4)0.034 (2)
C220.3058 (8)0.6197 (15)0.0722 (4)0.0318 (19)
Cu10.53605 (7)0.57406 (18)0.14968 (5)0.0334 (3)
N10.5685 (7)0.3386 (13)0.2325 (4)0.0371 (17)
N20.3577 (6)0.4658 (13)0.1233 (4)0.0356 (17)
N30.4985 (6)0.8001 (14)0.0644 (4)0.0395 (18)
O10.7056 (5)0.6288 (11)0.1368 (3)0.0435 (15)
O20.4696 (6)0.8527 (10)0.2200 (3)0.0424 (15)
O30.3679 (11)0.9784 (15)0.3112 (5)0.115 (4)
O1W0.8120 (8)0.4982 (17)0.0081 (4)0.069 (2)
O2W0.3434 (9)1.0079 (17)0.4542 (6)0.079 (3)
H2WA0.324 (7)0.878 (8)0.476 (4)0.02 (2)*
H2WB0.34 (2)0.958 (18)0.411 (2)0.08 (12)*
H1A0.512 (8)0.190 (16)0.229 (5)0.04 (2)*
H1WA0.816 (12)0.639 (8)0.011 (5)0.10 (5)*
H1WB0.781 (9)0.534 (16)0.047 (3)0.06 (3)*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Br10.0425 (7)0.1019 (10)0.0674 (8)0.0062 (7)0.0160 (6)0.0039 (8)
C10.035 (5)0.035 (5)0.038 (5)0.007 (4)0.001 (4)0.001 (4)
C20.038 (6)0.041 (6)0.054 (6)0.008 (4)0.008 (5)0.010 (5)
C30.029 (5)0.061 (6)0.057 (6)0.004 (5)0.005 (5)0.010 (6)
C40.043 (6)0.042 (6)0.046 (5)0.003 (4)0.002 (4)0.013 (5)
C50.037 (6)0.040 (5)0.045 (6)0.007 (4)0.002 (5)0.001 (5)
C60.036 (5)0.028 (5)0.041 (5)0.006 (4)0.006 (4)0.004 (4)
C70.036 (5)0.030 (5)0.046 (5)0.004 (4)0.007 (4)0.002 (4)
C80.046 (6)0.066 (7)0.037 (5)0.017 (5)0.001 (4)0.005 (5)
C90.059 (6)0.044 (6)0.039 (5)0.008 (5)0.014 (5)0.011 (5)
C100.051 (6)0.034 (5)0.058 (6)0.008 (4)0.011 (5)0.001 (5)
C110.046 (6)0.047 (6)0.042 (5)0.000 (5)0.003 (5)0.001 (5)
C120.037 (6)0.069 (7)0.062 (7)0.019 (5)0.015 (5)0.006 (6)
C130.034 (5)0.074 (7)0.059 (6)0.009 (6)0.003 (5)0.024 (6)
C140.039 (5)0.057 (6)0.044 (5)0.007 (5)0.004 (4)0.015 (5)
C150.040 (6)0.075 (7)0.045 (6)0.012 (5)0.020 (5)0.017 (6)
C160.055 (7)0.070 (7)0.039 (5)0.021 (6)0.013 (5)0.003 (5)
C170.055 (6)0.046 (6)0.028 (5)0.009 (5)0.006 (4)0.004 (4)
C180.076 (8)0.046 (6)0.040 (6)0.007 (5)0.001 (6)0.012 (5)
C190.067 (8)0.068 (8)0.040 (6)0.002 (6)0.014 (5)0.019 (5)
C200.040 (6)0.050 (6)0.041 (5)0.004 (4)0.011 (4)0.009 (5)
C210.041 (5)0.039 (5)0.024 (4)0.004 (4)0.006 (4)0.009 (4)
C220.043 (5)0.027 (5)0.026 (4)0.002 (4)0.002 (4)0.004 (4)
Cu10.0305 (6)0.0357 (5)0.0343 (5)0.0019 (6)0.0034 (5)0.0016 (6)
N10.036 (4)0.027 (4)0.050 (4)0.003 (3)0.010 (4)0.003 (3)
N20.036 (4)0.030 (4)0.042 (4)0.001 (3)0.004 (3)0.007 (3)
N30.033 (4)0.051 (5)0.035 (4)0.006 (4)0.005 (3)0.002 (4)
O10.023 (3)0.057 (4)0.051 (4)0.003 (3)0.005 (3)0.011 (3)
O20.056 (4)0.033 (3)0.039 (3)0.004 (3)0.014 (3)0.004 (3)
O30.197 (11)0.056 (5)0.103 (7)0.055 (6)0.098 (8)0.029 (5)
O1W0.074 (6)0.093 (7)0.040 (4)0.009 (5)0.011 (4)0.007 (4)
O2W0.078 (6)0.079 (7)0.083 (7)0.008 (5)0.029 (5)0.012 (5)
Geometric parameters (Å, º) top
Br1—C41.883 (10)C13—C141.412 (14)
C1—O11.336 (10)C13—H130.9300
C1—C21.393 (12)C14—C221.407 (12)
C1—C61.414 (11)C14—C151.424 (13)
C2—C31.372 (13)C15—C161.357 (14)
C2—H20.9300C15—H150.9300
C3—C41.376 (13)C16—C171.424 (14)
C3—H30.9300C16—H160.9300
C4—C51.385 (13)C17—C211.383 (12)
C5—C61.373 (12)C17—C181.389 (14)
C5—H50.9300C18—C191.354 (14)
C6—C71.505 (11)C18—H180.9300
C7—N11.499 (11)C19—C201.394 (13)
C7—H7A0.9700C19—H190.9300
C7—H7B0.9700C20—N31.315 (11)
C8—N11.472 (11)C20—H200.9300
C8—C91.513 (12)C21—N31.362 (11)
C8—H8A0.9700C21—C221.434 (12)
C8—H8B0.9700C22—N21.354 (10)
C9—C101.496 (12)Cu1—O11.937 (6)
C9—H9A0.9700Cu1—N11.997 (7)
C9—H9B0.9700Cu1—N32.009 (7)
C10—O31.231 (11)Cu1—N22.096 (7)
C10—O21.270 (11)Cu1—O22.141 (6)
C11—N21.336 (11)N1—H1A1.01 (9)
C11—C121.399 (13)O1W—H1WA0.84 (6)
C11—H110.9300O1W—H1WB0.84 (7)
C12—C131.368 (15)O2W—H2WA0.84 (6)
C12—H120.9300O2W—H2WB0.84 (6)
O1—C1—C2121.2 (8)C16—C15—C14120.8 (9)
O1—C1—C6120.6 (8)C16—C15—H15119.6
C2—C1—C6118.0 (8)C14—C15—H15119.6
C3—C2—C1121.7 (9)C15—C16—C17121.3 (9)
C3—C2—H2119.2C15—C16—H16119.3
C1—C2—H2119.2C17—C16—H16119.3
C2—C3—C4119.6 (9)C21—C17—C18117.0 (9)
C2—C3—H3120.2C21—C17—C16118.8 (9)
C4—C3—H3120.2C18—C17—C16124.2 (9)
C3—C4—C5120.1 (9)C19—C18—C17119.9 (9)
C3—C4—Br1121.1 (7)C19—C18—H18120.0
C5—C4—Br1118.7 (8)C17—C18—H18120.0
C6—C5—C4120.9 (9)C18—C19—C20119.5 (9)
C6—C5—H5119.6C18—C19—H19120.2
C4—C5—H5119.6C20—C19—H19120.2
C5—C6—C1119.7 (8)N3—C20—C19122.5 (9)
C5—C6—C7120.7 (8)N3—C20—H20118.8
C1—C6—C7119.6 (8)C19—C20—H20118.8
N1—C7—C6111.9 (7)N3—C21—C17123.6 (8)
N1—C7—H7A109.2N3—C21—C22115.4 (7)
C6—C7—H7A109.2C17—C21—C22121.0 (9)
N1—C7—H7B109.2N2—C22—C14123.0 (8)
C6—C7—H7B109.2N2—C22—C21118.1 (8)
H7A—C7—H7B107.9C14—C22—C21118.8 (8)
N1—C8—C9113.2 (8)O1—Cu1—N193.3 (3)
N1—C8—H8A108.9O1—Cu1—N388.3 (3)
C9—C8—H8A108.9N1—Cu1—N3177.5 (3)
N1—C8—H8B108.9O1—Cu1—N2158.2 (3)
C9—C8—H8B108.9N1—Cu1—N297.2 (3)
H8A—C8—H8B107.8N3—Cu1—N280.7 (3)
C10—C9—C8114.1 (8)O1—Cu1—O2110.0 (3)
C10—C9—H9A108.7N1—Cu1—O292.1 (3)
C8—C9—H9A108.7N3—Cu1—O289.1 (2)
C10—C9—H9B108.7N2—Cu1—O288.8 (3)
C8—C9—H9B108.7C8—N1—C7109.8 (7)
H9A—C9—H9B107.6C8—N1—Cu1114.3 (6)
O3—C10—O2121.8 (9)C7—N1—Cu1111.6 (5)
O3—C10—C9119.0 (8)C8—N1—H1A111 (5)
O2—C10—C9119.2 (8)C7—N1—H1A98 (5)
N2—C11—C12121.8 (9)Cu1—N1—H1A112 (5)
N2—C11—H11119.1C11—N2—C22118.3 (8)
C12—C11—H11119.1C11—N2—Cu1130.8 (6)
C13—C12—C11120.7 (9)C22—N2—Cu1110.4 (5)
C13—C12—H12119.7C20—N3—C21117.5 (8)
C11—C12—H12119.7C20—N3—Cu1127.7 (6)
C12—C13—C14118.5 (9)C21—N3—Cu1114.4 (6)
C12—C13—H13120.8C1—O1—Cu1125.1 (6)
C14—C13—H13120.8C10—O2—Cu1126.5 (6)
C22—C14—C13117.6 (9)H1WA—O1W—H1WB101 (9)
C22—C14—C15119.3 (9)H2WA—O2W—H2WB101 (9)
C13—C14—C15123.1 (9)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N1—H1A···O2i1.01 (9)1.88 (9)2.841 (9)157 (7)
N1—H1A···O3i1.01 (9)2.54 (9)3.349 (12)136 (6)
O1W—H1WB···O10.84 (6)1.96 (7)2.800 (9)178 (9)
O1W—H1WA···O2Wii0.84 (6)2.03 (5)2.865 (13)172 (18)
O2W—H2WA···O1Wiii0.84 (6)2.12 (5)2.926 (13)162 (6)
O2W—H2WB···O30.84 (7)1.88 (3)2.667 (13)157 (8)
Symmetry codes: (i) x, y1, z; (ii) x+1/2, y+2, z1/2; (iii) x1/2, y+1, z+1/2.
 

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