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In the title complex, [Zn(C16H13Br2NO3)(C12H8N2)]·2H2O or [Zn(L)(phen)]·2H2O, [LH2 = 2-(3,5-dibromo-2-hydr­oxy-benzyl­amino)-3-phenylpropionic acid and phen = 1,10-phenanthroline], the ZnII 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, complex mol­ecules are linked into a chain along the c axis through N—H...O hydrogen bonds; the water mol­ecules are connected to the chains via O—H...O hydrogen bonds.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536807000177/ci2225sup1.cif
Contains datablocks global, I

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536807000177/ci2225Isup2.hkl
Contains datablock I

CCDC reference: 636196

Key indicators

  • Single-crystal X-ray study
  • T = 294 K
  • Mean [sigma](C-C) = 0.010 Å
  • R factor = 0.054
  • wR factor = 0.165
  • Data-to-parameter ratio = 18.6

checkCIF/PLATON results

No syntax errors found



Alert level B PLAT420_ALERT_2_B D-H Without Acceptor O1W - H1WA ... ?
Alert level C PLAT026_ALERT_3_C Ratio Observed / Unique Reflections too Low .... 45 Perc. PLAT042_ALERT_1_C Calc. and Rep. MoietyFormula Strings Differ .... ? PLAT066_ALERT_1_C Predicted and Reported Transmissions Identical . ? PLAT242_ALERT_2_C Check Low Ueq as Compared to Neighbors for C13 PLAT341_ALERT_3_C Low Bond Precision on C-C bonds (x 1000) Ang ... 10 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: C28 H25 Br2 N3 O5 Zn1 Atom count from _chemical_formula_moiety:
0 ALERT level A = In general: serious problem 1 ALERT level B = Potentially serious problem 6 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 2 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 1 ALERT type 4 Improvement, methodology, query or suggestion 0 ALERT type 5 Informative message, check

Computing details top

Data collection: SMART (Bruker, 2004); cell refinement: SAINT (Bruker, 2004); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997a); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997a); molecular graphics: SHELXTL (Sheldrick, 1997b); software used to prepare material for publication: SHELXTL.

{2-[(3,5-Dibromo-2-oxidophenyl)methylamino]-3-phenylpropanoato-k3N,O,O'} (1,10-phenanthroline-k2N,N')zinc(II) dihydrate top
Crystal data top
[Zn(C16H13Br2NO3)(C12H8N2)]·2H2OF(000) = 1416
Mr = 708.72Dx = 1.655 Mg m3
Monoclinic, P21/cMo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybcCell parameters from 5694 reflections
a = 9.5929 (11) Åθ = 1–27.5°
b = 25.969 (3) ŵ = 3.72 mm1
c = 11.9430 (13) ÅT = 294 K
β = 107.101 (2)°Plate, colourless
V = 2843.7 (6) Å30.34 × 0.28 × 0.10 mm
Z = 4
Data collection top
Bruker SMART CCD area-detector
diffractometer
6547 independent reflections
Radiation source: fine-focus sealed tube2965 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.087
φ and ω scansθmax = 27.6°, θmin = 1.6°
Absorption correction: multi-scan
(SADABS; Sheldrick, 1996)
h = 1211
Tmin = 0.299, Tmax = 0.690k = 3332
18930 measured reflectionsl = 1215
Refinement top
Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.054Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.165H-atom parameters constrained
S = 0.97 w = 1/[σ2(Fo2) + (0.0638P)2 + 3.5289P]
where P = (Fo2 + 2Fc2)/3
6547 reflections(Δ/σ)max = 0.001
352 parametersΔρmax = 0.93 e Å3
0 restraintsΔρmin = 1.19 e Å3
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
Br10.49859 (9)0.00194 (3)0.81733 (7)0.0637 (3)
Br20.80993 (14)0.14671 (4)1.15012 (8)0.1247 (5)
Zn10.23347 (8)0.13833 (3)0.62993 (6)0.0379 (2)
O10.2344 (5)0.17181 (17)0.4732 (3)0.0489 (11)
O20.4166 (5)0.09892 (16)0.6683 (3)0.0469 (11)
O30.2689 (6)0.2474 (2)0.3979 (4)0.0783 (17)
N10.3210 (5)0.20988 (18)0.6926 (4)0.0366 (12)
H1B0.29340.21970.75610.044*
N20.1735 (5)0.11288 (18)0.7854 (4)0.0405 (12)
N30.0548 (5)0.09340 (18)0.5547 (4)0.0378 (12)
C10.2691 (7)0.2463 (2)0.5956 (5)0.0420 (16)
H1A0.34010.27440.60670.050*
C20.2575 (7)0.2205 (3)0.4794 (6)0.0484 (17)
C30.1207 (7)0.2695 (2)0.5940 (6)0.0516 (18)
H3A0.13440.28870.66610.062*
H3B0.09290.29410.53000.062*
C40.0049 (7)0.2332 (2)0.5814 (6)0.0476 (17)
C50.0951 (8)0.2193 (3)0.4717 (7)0.062 (2)
H5A0.07420.23100.40480.074*
C60.2152 (9)0.1884 (3)0.4604 (8)0.073 (2)
H6A0.27540.17960.38650.088*
C70.2457 (9)0.1704 (3)0.5596 (10)0.078 (3)
H7A0.32660.14950.55240.094*
C80.1566 (9)0.1834 (3)0.6692 (8)0.072 (2)
H8A0.17620.17090.73590.086*
C90.0377 (8)0.2151 (3)0.6795 (6)0.0522 (18)
H9A0.02090.22450.75350.063*
C100.4826 (7)0.2039 (2)0.7227 (5)0.0440 (16)
H10A0.52870.23600.75520.053*
H10B0.50870.19690.65170.053*
C110.5404 (7)0.1610 (2)0.8098 (5)0.0408 (15)
C120.6298 (7)0.1712 (3)0.9208 (6)0.0557 (19)
H12A0.65510.20500.94330.067*
C130.6818 (8)0.1321 (3)0.9982 (6)0.064 (2)
C140.6452 (8)0.0819 (3)0.9693 (6)0.060 (2)
H14A0.68000.05561.02310.072*
C150.5544 (7)0.0711 (2)0.8572 (6)0.0467 (17)
C160.5010 (7)0.1098 (2)0.7747 (5)0.0409 (15)
C170.0040 (7)0.0856 (2)0.4407 (6)0.0442 (16)
H17A0.03600.10250.38870.053*
C180.1242 (7)0.0530 (3)0.3956 (6)0.0541 (19)
H18A0.16100.04760.31530.065*
C190.1859 (7)0.0297 (3)0.4709 (6)0.0530 (19)
H19A0.26570.00810.44220.064*
C200.1297 (7)0.0379 (2)0.5924 (6)0.0441 (16)
C210.1875 (8)0.0148 (3)0.6765 (7)0.061 (2)
H21A0.26680.00740.65210.073*
C220.1285 (8)0.0246 (3)0.7922 (7)0.061 (2)
H22A0.16920.00930.84570.073*
C230.0054 (7)0.0578 (2)0.8343 (6)0.0491 (17)
C240.0608 (8)0.0701 (3)0.9526 (6)0.060 (2)
H24A0.02330.05631.00960.072*
C250.1778 (8)0.1017 (3)0.9852 (6)0.0541 (19)
H25A0.22110.10971.06360.065*
C260.2320 (8)0.1219 (2)0.8973 (5)0.0488 (17)
H26A0.31420.14280.91990.059*
C270.0568 (6)0.0803 (2)0.7530 (5)0.0386 (15)
C280.0062 (6)0.0704 (2)0.6306 (6)0.0385 (15)
O1W0.3519 (11)0.1287 (3)0.2945 (6)0.170 (4)
H1WB0.33550.15540.32950.204*
H1WA0.26230.12150.27770.204*
O2W0.4820 (5)0.0545 (2)0.4845 (5)0.0827 (17)
H2WB0.45350.07900.43450.099*
H2WA0.47370.06410.55030.099*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Br10.0648 (5)0.0493 (4)0.0709 (5)0.0102 (4)0.0103 (4)0.0024 (4)
Br20.1705 (11)0.1065 (8)0.0534 (6)0.0640 (8)0.0352 (6)0.0164 (5)
Zn10.0434 (4)0.0370 (4)0.0331 (4)0.0036 (3)0.0109 (3)0.0011 (3)
O10.062 (3)0.055 (3)0.031 (2)0.004 (2)0.017 (2)0.002 (2)
O20.047 (3)0.058 (3)0.031 (2)0.009 (2)0.005 (2)0.010 (2)
O30.109 (4)0.087 (4)0.044 (3)0.009 (3)0.030 (3)0.029 (3)
N10.045 (3)0.040 (3)0.029 (3)0.003 (2)0.017 (2)0.004 (2)
N20.043 (3)0.037 (3)0.042 (3)0.006 (2)0.013 (3)0.004 (2)
N30.042 (3)0.036 (3)0.033 (3)0.002 (2)0.008 (2)0.000 (2)
C10.051 (4)0.034 (3)0.046 (4)0.006 (3)0.022 (3)0.009 (3)
C20.049 (4)0.059 (4)0.042 (4)0.001 (4)0.020 (3)0.015 (4)
C30.055 (4)0.038 (4)0.062 (4)0.004 (3)0.018 (4)0.009 (3)
C40.051 (4)0.039 (4)0.057 (5)0.007 (3)0.024 (4)0.001 (3)
C50.053 (5)0.066 (5)0.066 (5)0.015 (4)0.017 (4)0.002 (4)
C60.047 (5)0.080 (6)0.088 (7)0.018 (4)0.012 (5)0.010 (5)
C70.053 (5)0.054 (5)0.137 (9)0.017 (4)0.043 (6)0.000 (6)
C80.065 (6)0.067 (5)0.097 (7)0.024 (5)0.047 (5)0.003 (5)
C90.054 (5)0.049 (4)0.057 (5)0.002 (4)0.020 (4)0.003 (3)
C100.045 (4)0.045 (4)0.041 (4)0.011 (3)0.010 (3)0.001 (3)
C110.042 (4)0.048 (4)0.033 (3)0.008 (3)0.012 (3)0.000 (3)
C120.057 (5)0.061 (4)0.046 (4)0.024 (4)0.009 (3)0.000 (4)
C130.070 (5)0.068 (5)0.041 (4)0.028 (4)0.003 (4)0.006 (4)
C140.056 (5)0.063 (5)0.053 (5)0.011 (4)0.004 (4)0.019 (4)
C150.042 (4)0.050 (4)0.045 (4)0.007 (3)0.007 (3)0.001 (3)
C160.039 (4)0.049 (4)0.040 (4)0.003 (3)0.019 (3)0.002 (3)
C170.047 (4)0.039 (3)0.043 (4)0.001 (3)0.008 (3)0.002 (3)
C180.044 (4)0.058 (4)0.052 (4)0.002 (4)0.001 (4)0.007 (4)
C190.037 (4)0.048 (4)0.063 (5)0.003 (3)0.003 (4)0.002 (4)
C200.037 (4)0.038 (3)0.053 (4)0.000 (3)0.007 (3)0.007 (3)
C210.041 (4)0.054 (4)0.083 (6)0.011 (3)0.010 (4)0.011 (4)
C220.043 (4)0.071 (5)0.072 (5)0.011 (4)0.020 (4)0.020 (4)
C230.047 (4)0.048 (4)0.054 (4)0.006 (3)0.018 (3)0.014 (3)
C240.072 (5)0.064 (5)0.048 (5)0.004 (4)0.026 (4)0.019 (4)
C250.068 (5)0.055 (4)0.037 (4)0.001 (4)0.013 (4)0.004 (3)
C260.070 (5)0.043 (4)0.034 (4)0.005 (3)0.016 (3)0.002 (3)
C270.039 (4)0.038 (3)0.036 (4)0.005 (3)0.008 (3)0.008 (3)
C280.034 (4)0.030 (3)0.051 (4)0.003 (3)0.011 (3)0.006 (3)
O1W0.247 (10)0.170 (8)0.087 (5)0.108 (7)0.040 (6)0.011 (5)
O2W0.080 (4)0.098 (4)0.071 (4)0.010 (3)0.023 (3)0.025 (3)
Geometric parameters (Å, º) top
Br1—C151.896 (6)C10—H10A0.97
Br2—C131.907 (7)C10—H10B0.97
Zn1—O21.968 (4)C11—C121.376 (8)
Zn1—N32.049 (5)C11—C161.413 (8)
Zn1—O12.067 (4)C12—C131.365 (9)
Zn1—N12.085 (5)C12—H12A0.93
Zn1—N22.201 (5)C13—C141.368 (10)
O1—C21.282 (8)C14—C151.394 (9)
O2—C161.320 (7)C14—H14A0.93
O3—C21.228 (7)C15—C161.394 (8)
N1—C11.464 (7)C17—C181.404 (8)
N1—C101.492 (7)C17—H17A0.93
N1—H1B0.91C18—C191.357 (9)
N2—C261.310 (8)C18—H18A0.93
N2—C271.365 (7)C19—C201.407 (9)
N3—C171.327 (7)C19—H19A0.93
N3—C281.354 (7)C20—C281.415 (8)
C1—C21.516 (9)C20—C211.417 (9)
C1—C31.541 (9)C21—C221.354 (10)
C1—H1A0.98C21—H21A0.93
C3—C41.502 (9)C22—C231.429 (9)
C3—H3A0.97C22—H22A0.93
C3—H3B0.97C23—C241.406 (9)
C4—C91.382 (9)C23—C271.408 (9)
C4—C51.390 (9)C24—C251.351 (9)
C5—C61.377 (10)C24—H24A0.93
C5—H5A0.93C25—C261.403 (9)
C6—C71.383 (12)C25—H25A0.93
C6—H6A0.93C26—H26A0.93
C7—C81.378 (11)C27—C281.432 (8)
C7—H7A0.93O1W—H1WB0.85
C8—C91.383 (10)O1W—H1WA0.84
C8—H8A0.93O2W—H2WB0.86
C9—H9A0.93O2W—H2WA0.85
C10—C111.513 (8)
O2—Zn1—N3112.36 (18)N1—C10—H10B109.0
O2—Zn1—O1100.86 (18)C11—C10—H10B109.0
N3—Zn1—O193.93 (18)H10A—C10—H10B107.8
O2—Zn1—N198.17 (18)C12—C11—C16120.2 (6)
N3—Zn1—N1149.45 (19)C12—C11—C10121.3 (6)
O1—Zn1—N180.90 (17)C16—C11—C10118.5 (5)
O2—Zn1—N294.83 (18)C13—C12—C11120.7 (6)
N3—Zn1—N278.83 (19)C13—C12—H12A119.7
O1—Zn1—N2164.26 (18)C11—C12—H12A119.7
N1—Zn1—N298.17 (18)C12—C13—C14121.5 (6)
C2—O1—Zn1114.2 (4)C12—C13—Br2120.1 (5)
C16—O2—Zn1111.5 (4)C14—C13—Br2118.4 (5)
C1—N1—C10110.2 (4)C13—C14—C15118.3 (6)
C1—N1—Zn1106.5 (3)C13—C14—H14A120.8
C10—N1—Zn1105.9 (4)C15—C14—H14A120.8
C1—N1—H1B111.4C14—C15—C16122.1 (6)
C10—N1—H1B111.4C14—C15—Br1118.8 (5)
Zn1—N1—H1B111.3C16—C15—Br1119.1 (5)
C26—N2—C27118.0 (6)O2—C16—C15121.4 (6)
C26—N2—Zn1131.9 (4)O2—C16—C11121.4 (5)
C27—N2—Zn1110.0 (4)C15—C16—C11117.2 (6)
C17—N3—C28118.8 (5)N3—C17—C18122.6 (6)
C17—N3—Zn1125.8 (4)N3—C17—H17A118.7
C28—N3—Zn1115.4 (4)C18—C17—H17A118.7
N1—C1—C2110.9 (5)C19—C18—C17118.9 (7)
N1—C1—C3111.2 (5)C19—C18—H18A120.5
C2—C1—C3110.1 (5)C17—C18—H18A120.5
N1—C1—H1A108.2C18—C19—C20120.4 (6)
C2—C1—H1A108.2C18—C19—H19A119.8
C3—C1—H1A108.2C20—C19—H19A119.8
O3—C2—O1124.7 (7)C19—C20—C28117.0 (6)
O3—C2—C1118.4 (6)C19—C20—C21123.7 (6)
O1—C2—C1116.9 (5)C28—C20—C21119.3 (6)
C4—C3—C1117.8 (5)C22—C21—C20120.7 (6)
C4—C3—H3A107.9C22—C21—H21A119.6
C1—C3—H3A107.9C20—C21—H21A119.6
C4—C3—H3B107.9C21—C22—C23121.8 (7)
C1—C3—H3B107.9C21—C22—H22A119.1
H3A—C3—H3B107.2C23—C22—H22A119.1
C9—C4—C5118.5 (7)C24—C23—C27116.2 (6)
C9—C4—C3120.3 (6)C24—C23—C22125.0 (7)
C5—C4—C3121.1 (6)C27—C23—C22118.8 (7)
C6—C5—C4121.0 (7)C25—C24—C23121.3 (7)
C6—C5—H5A119.5C25—C24—H24A119.4
C4—C5—H5A119.5C23—C24—H24A119.4
C5—C6—C7119.7 (8)C24—C25—C26118.1 (7)
C5—C6—H6A120.2C24—C25—H25A120.9
C7—C6—H6A120.2C26—C25—H25A120.9
C8—C7—C6120.1 (8)N2—C26—C25123.7 (7)
C8—C7—H7A119.9N2—C26—H26A118.2
C6—C7—H7A119.9C25—C26—H26A118.2
C7—C8—C9119.7 (8)N2—C27—C23122.7 (6)
C7—C8—H8A120.1N2—C27—C28117.8 (5)
C9—C8—H8A120.1C23—C27—C28119.4 (6)
C4—C9—C8121.0 (7)N3—C28—C20122.2 (6)
C4—C9—H9A119.5N3—C28—C27117.9 (5)
C8—C9—H9A119.5C20—C28—C27119.9 (6)
N1—C10—C11112.8 (5)H1WB—O1W—H1WA88.6
N1—C10—H10A109.0H2WB—O2W—H2WA109.2
C11—C10—H10A109.0
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N1—H1B···O3i0.911.972.865 (7)167
O1W—H1WB···O10.852.252.914 (9)136
O2W—H2WB···O1W0.862.112.958 (9)169
O2W—H2WA···O20.851.892.712 (6)163
Symmetry code: (i) x, y+1/2, z+1/2.
 

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