(3,5-Dibromo-2-oxidobenzoato-κ2O,O′)(1,10-phenanthroline-κ2N,N′)copper(II) monohydrate

Zhang, S.-H.; Feng, X.-Z.; Li, G.-Z.; Jing, L.-X.; Liu, Z.

doi:10.1107/S1600536807012846

(3,5-Dibromo-2-oxidobenzoato-κ²O,O′)(1,10-phenanthroline-κ²N,N′)copper(II) monohydrate

S.-H. Zhang, X.-Z. Feng, G.-Z. Li, L.-X. Jing and Z. Liu

In the title complex, [Cu(C₇H₂Br₂O₃)(C₁₂H₈N₂)]·H₂O, the Cu^II atom is coordinated in a slightly distorted square-planar geometry by two O atoms from a 3,5-dibromo-2-oxidobenzoate dianion and two N atoms from 1,10-phenanthroline. The Cu^II complex and water molecules are linked into chains through O—H

O hydrogen bonds.

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Supporting information

	Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536807012846/ng2238sup1.cif Contains datablocks global, I
	Structure factor file (CIF format) https://doi.org/10.1107/S1600536807012846/ng2238Isup2.hkl Contains datablock I

CCDC reference: 643073

checkCIF report

Key indicators

Single-crystal X-ray study
T = 298 K
Mean (C-C) = 0.010 Å
R factor = 0.050
wR factor = 0.095
Data-to-parameter ratio = 12.6

checkCIF/PLATON results

No syntax errors found



Alert level C
PLAT048_ALERT_1_C MoietyFormula Not Given ........................          ?
PLAT062_ALERT_4_C Rescale T(min) & T(max) by .....................       0.86
PLAT125_ALERT_4_C No _symmetry_space_group_name_Hall Given .......          ?
PLAT220_ALERT_2_C Large Non-Solvent    C     Ueq(max)/Ueq(min) ...       2.68 Ratio
PLAT241_ALERT_2_C Check High      Ueq as Compared to Neighbors for        C18
PLAT341_ALERT_3_C Low Bond Precision on C-C bonds (x 1000) Ang ...         10
PLAT710_ALERT_4_C Delete 1-2-3 or 2-3-4 Linear Torsion Angle ... #          1
            O3  -CU1 -N1  -C8   -158.80  1.10   1.555   1.555   1.555   1.555
PLAT710_ALERT_4_C Delete 1-2-3 or 2-3-4 Linear Torsion Angle ... #          4
            O3  -CU1 -N1  -C12    22.50  1.60   1.555   1.555   1.555   1.555
PLAT710_ALERT_4_C Delete 1-2-3 or 2-3-4 Linear Torsion Angle ... #          8
            O1  -CU1 -N2  -C17   150.80  1.70   1.555   1.555   1.555   1.555
PLAT710_ALERT_4_C Delete 1-2-3 or 2-3-4 Linear Torsion Angle ... #         11
            O1  -CU1 -N2  -C13   -27.00  2.00   1.555   1.555   1.555   1.555
PLAT710_ALERT_4_C Delete 1-2-3 or 2-3-4 Linear Torsion Angle ... #         14
            N2  -CU1 -O1  -C1   -153.40  1.70   1.555   1.555   1.555   1.555
PLAT710_ALERT_4_C Delete 1-2-3 or 2-3-4 Linear Torsion Angle ... #         18
            N1  -CU1 -O3  -C3    162.20  1.20   1.555   1.555   1.555   1.555

Alert level G
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      0.857
            Tmax scaled      0.383 Tmin scaled      0.167

   0 ALERT level A = In general: serious problem
   0 ALERT level B = Potentially serious problem
  12 ALERT level C = Check and explain
   1 ALERT level G = General alerts; check

   1 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
   8 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.

(3,5-Dibromo-2-oxidobenzoato-κ²O,O')(1,10-phenanthroline- κ²N,N')copper(II) monohydrate top

Crystal data top

[Cu(C₇H₂Br₂O₃)(C₁₂H₈N₂)]·H₂O	F(000) = 1084
M_r = 555.67	D_x = 2.038 Mg m⁻³
Monoclinic, P2₁/c	Mo Kα radiation, λ = 0.71073 Å
a = 4.7831 (11) Å	Cell parameters from 2274 reflections
b = 20.382 (3) Å	θ = 2.2–24.4°
c = 18.710 (2) Å	µ = 5.65 mm⁻¹
β = 96.795 (2)°	T = 298 K
V = 1811.1 (5) Å³	Prism, blue
Z = 4	0.43 × 0.22 × 0.17 mm

Data collection top

Bruker SMART CCD area-detector diffractometer	3186 independent reflections
Radiation source: fine-focus sealed tube	1791 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.084
φ and ω scans	θ_max = 25.0°, θ_min = 1.5°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −5→5
T_min = 0.195, T_max = 0.447	k = −16→24
9123 measured reflections	l = −21→22

Refinement top

Refinement on F²	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F² > 2σ(F²)] = 0.050	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.095	H-atom parameters constrained
S = 1.00	w = 1/[σ²(F_o²) + (0.0294P)²] where P = (F_o² + 2F_c²)/3
3186 reflections	(Δ/σ)_max = 0.001
253 parameters	Δρ_max = 0.95 e Å⁻³
0 restraints	Δρ_min = −0.48 e Å⁻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	U_iso*/U_eq
Cu1	0.10239 (16)	0.36006 (4)	0.21037 (4)	0.0395 (3)
Br1	0.63172 (17)	0.32124 (4)	0.43753 (4)	0.0552 (3)
Br2	1.26707 (15)	0.54877 (4)	0.40010 (4)	0.0494 (2)
N1	−0.1911 (11)	0.3510 (3)	0.1253 (3)	0.0426 (16)
N2	−0.0787 (11)	0.2784 (3)	0.2409 (3)	0.0397 (15)
O1	0.2598 (10)	0.4343 (2)	0.1711 (2)	0.0428 (12)
O2	0.5406 (10)	0.5194 (3)	0.1647 (2)	0.0580 (15)
O3	0.3674 (9)	0.3548 (2)	0.2914 (2)	0.0378 (11)
O4	−0.0006 (12)	0.5557 (3)	0.0841 (3)	0.109 (2)
H1	−0.1389	0.5492	0.1078	0.163*
H2	0.1462	0.5488	0.1134	0.163*
C1	0.4715 (15)	0.4705 (4)	0.1968 (4)	0.0370 (18)
C2	0.6353 (13)	0.4531 (3)	0.2683 (3)	0.0288 (16)
C3	0.5635 (12)	0.3987 (3)	0.3100 (3)	0.0280 (16)
C4	0.7245 (13)	0.3915 (3)	0.3786 (3)	0.0305 (16)
C5	0.9316 (12)	0.4342 (3)	0.4044 (3)	0.0315 (17)
H5	1.0306	0.4278	0.4497	0.038*
C6	0.9942 (13)	0.4877 (3)	0.3626 (3)	0.0318 (17)
C7	0.8484 (13)	0.4957 (3)	0.2957 (3)	0.0344 (17)
H7	0.8936	0.5309	0.2675	0.041*
C8	−0.2403 (15)	0.3902 (4)	0.0681 (4)	0.053 (2)
H8	−0.1281	0.4270	0.0646	0.064*
C9	−0.4575 (18)	0.3767 (5)	0.0134 (4)	0.072 (3)
H9	−0.4877	0.4043	−0.0263	0.086*
C10	−0.6229 (18)	0.3241 (5)	0.0181 (4)	0.068 (3)
H10	−0.7678	0.3157	−0.0184	0.081*
C11	−0.5800 (15)	0.2818 (5)	0.0772 (4)	0.056 (2)
C12	−0.3588 (14)	0.2972 (4)	0.1307 (4)	0.043 (2)
C13	−0.2944 (14)	0.2585 (3)	0.1923 (4)	0.0382 (18)
C14	−0.4499 (15)	0.2016 (4)	0.2009 (4)	0.050 (2)
C15	−0.3708 (17)	0.1645 (4)	0.2630 (5)	0.068 (3)
H15	−0.4671	0.1261	0.2711	0.081*
C16	−0.1498 (17)	0.1850 (4)	0.3120 (4)	0.061 (2)
H16	−0.0951	0.1606	0.3533	0.073*
C17	−0.0110 (15)	0.2425 (4)	0.2987 (4)	0.050 (2)
H17	0.1365	0.2564	0.3321	0.060*
C18	−0.7338 (17)	0.2234 (5)	0.0869 (5)	0.075 (3)
H18	−0.8782	0.2111	0.0517	0.090*
C19	−0.6755 (15)	0.1856 (4)	0.1456 (5)	0.061 (2)
H19	−0.7832	0.1483	0.1506	0.073*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Cu1	0.0312 (5)	0.0464 (6)	0.0393 (5)	0.0026 (4)	−0.0030 (4)	−0.0102 (4)
Br1	0.0615 (6)	0.0538 (6)	0.0466 (5)	−0.0170 (4)	−0.0085 (4)	0.0158 (4)
Br2	0.0385 (5)	0.0479 (5)	0.0608 (5)	−0.0118 (4)	0.0015 (4)	−0.0094 (4)
N1	0.037 (4)	0.050 (4)	0.040 (4)	0.010 (3)	0.000 (3)	−0.013 (3)
N2	0.039 (4)	0.035 (4)	0.045 (4)	0.003 (3)	0.002 (3)	−0.012 (3)
O1	0.044 (3)	0.047 (3)	0.036 (3)	−0.003 (3)	−0.002 (2)	0.003 (2)
O2	0.064 (4)	0.056 (4)	0.052 (3)	−0.010 (3)	0.001 (3)	0.020 (3)
O3	0.039 (3)	0.038 (3)	0.035 (2)	−0.009 (2)	−0.002 (2)	−0.001 (2)
O4	0.094 (5)	0.106 (6)	0.118 (5)	−0.016 (4)	−0.024 (4)	0.060 (4)
C1	0.037 (5)	0.031 (5)	0.044 (5)	0.012 (4)	0.008 (4)	−0.012 (4)
C2	0.032 (4)	0.029 (4)	0.025 (4)	0.007 (3)	0.004 (3)	−0.006 (3)
C3	0.022 (4)	0.031 (5)	0.031 (4)	0.006 (3)	0.003 (3)	−0.003 (3)
C4	0.035 (4)	0.021 (4)	0.035 (4)	−0.002 (3)	0.000 (3)	0.004 (3)
C5	0.025 (4)	0.041 (5)	0.027 (4)	0.003 (3)	−0.002 (3)	−0.010 (3)
C6	0.028 (4)	0.028 (4)	0.040 (4)	0.000 (3)	0.007 (3)	−0.003 (3)
C7	0.036 (4)	0.032 (4)	0.038 (4)	0.004 (4)	0.013 (3)	0.003 (4)
C8	0.046 (5)	0.069 (6)	0.044 (5)	0.016 (4)	0.000 (4)	−0.010 (5)
C9	0.054 (6)	0.108 (9)	0.050 (5)	0.007 (6)	−0.004 (5)	−0.017 (6)
C10	0.052 (6)	0.106 (9)	0.039 (5)	0.027 (6)	−0.017 (4)	−0.025 (6)
C11	0.028 (5)	0.082 (7)	0.058 (6)	0.007 (5)	−0.001 (4)	−0.051 (6)
C12	0.025 (4)	0.065 (6)	0.041 (5)	0.012 (4)	0.008 (4)	−0.020 (4)
C13	0.027 (4)	0.034 (5)	0.053 (5)	0.001 (4)	0.004 (4)	−0.031 (4)
C14	0.036 (5)	0.044 (6)	0.071 (6)	0.007 (4)	0.008 (4)	−0.027 (5)
C15	0.052 (6)	0.058 (6)	0.096 (7)	−0.018 (5)	0.017 (5)	−0.030 (6)
C16	0.067 (6)	0.046 (6)	0.070 (6)	−0.004 (5)	0.013 (5)	−0.001 (5)
C17	0.045 (5)	0.044 (6)	0.060 (5)	0.001 (4)	0.003 (4)	−0.007 (5)
C18	0.036 (6)	0.110 (9)	0.076 (7)	0.020 (6)	−0.011 (5)	−0.057 (7)
C19	0.026 (5)	0.054 (6)	0.103 (7)	−0.001 (4)	0.011 (5)	−0.050 (6)

Geometric parameters (Å, º) top

Cu1—O3	1.861 (4)	C6—C7	1.369 (8)
Cu1—O1	1.878 (4)	C7—H7	0.9300
Cu1—N2	1.991 (6)	C8—C9	1.396 (9)
Cu1—N1	2.002 (5)	C8—H8	0.9300
Br1—C4	1.892 (6)	C9—C10	1.341 (11)
Br2—C6	1.879 (6)	C9—H9	0.9300
N1—C8	1.335 (8)	C10—C11	1.399 (10)
N1—C12	1.369 (8)	C10—H10	0.9300
N2—C17	1.314 (8)	C11—C12	1.403 (9)
N2—C13	1.352 (7)	C11—C18	1.422 (11)
O1—C1	1.299 (7)	C12—C13	1.401 (9)
O2—C1	1.228 (7)	C13—C14	1.398 (9)
O3—C3	1.313 (7)	C14—C15	1.400 (10)
O4—H1	0.8500	C14—C19	1.441 (10)
O4—H2	0.8500	C15—C16	1.380 (9)
C1—C2	1.510 (8)	C15—H15	0.9300
C2—C7	1.390 (8)	C16—C17	1.385 (9)
C2—C3	1.422 (8)	C16—H16	0.9300
C3—C4	1.423 (7)	C17—H17	0.9300
C4—C5	1.364 (8)	C18—C19	1.344 (10)
C5—C6	1.394 (8)	C18—H18	0.9300
C5—H5	0.9300	C19—H19	0.9300

O3—Cu1—O1	95.74 (18)	N1—C8—C9	121.1 (8)
O3—Cu1—N2	89.7 (2)	N1—C8—H8	119.5
O1—Cu1—N2	173.6 (2)	C9—C8—H8	119.5
O3—Cu1—N1	171.2 (2)	C10—C9—C8	120.2 (9)
O1—Cu1—N1	92.3 (2)	C10—C9—H9	119.9
N2—Cu1—N1	82.1 (3)	C8—C9—H9	119.9
C8—N1—C12	119.3 (6)	C9—C10—C11	120.8 (8)
C8—N1—Cu1	128.5 (5)	C9—C10—H10	119.6
C12—N1—Cu1	112.2 (5)	C11—C10—H10	119.6
C17—N2—C13	118.8 (6)	C10—C11—C12	117.0 (9)
C17—N2—Cu1	128.8 (5)	C10—C11—C18	125.9 (8)
C13—N2—Cu1	112.4 (5)	C12—C11—C18	117.1 (9)
C1—O1—Cu1	130.1 (4)	N1—C12—C13	115.9 (7)
C3—O3—Cu1	124.9 (4)	N1—C12—C11	121.7 (8)
H1—O4—H2	105.7	C13—C12—C11	122.4 (8)
O2—C1—O1	121.5 (6)	N2—C13—C14	123.0 (7)
O2—C1—C2	118.9 (6)	N2—C13—C12	117.4 (7)
O1—C1—C2	119.6 (7)	C14—C13—C12	119.5 (7)
C7—C2—C3	120.0 (5)	C13—C14—C15	116.6 (7)
C7—C2—C1	117.4 (6)	C13—C14—C19	117.9 (8)
C3—C2—C1	122.4 (6)	C15—C14—C19	125.5 (8)
O3—C3—C2	126.7 (5)	C16—C15—C14	120.0 (8)
O3—C3—C4	117.5 (6)	C16—C15—H15	120.0
C2—C3—C4	115.8 (6)	C14—C15—H15	120.0
C5—C4—C3	123.1 (6)	C15—C16—C17	118.8 (8)
C5—C4—Br1	119.2 (5)	C15—C16—H16	120.6
C3—C4—Br1	117.6 (5)	C17—C16—H16	120.6
C4—C5—C6	119.7 (6)	N2—C17—C16	122.8 (7)
C4—C5—H5	120.1	N2—C17—H17	118.6
C6—C5—H5	120.1	C16—C17—H17	118.6
C7—C6—C5	119.1 (6)	C19—C18—C11	121.5 (8)
C7—C6—Br2	121.3 (5)	C19—C18—H18	119.2
C5—C6—Br2	119.6 (5)	C11—C18—H18	119.2
C6—C7—C2	122.3 (6)	C18—C19—C14	121.5 (8)
C6—C7—H7	118.8	C18—C19—H19	119.2
C2—C7—H7	118.8	C14—C19—H19	119.2

O3—Cu1—N1—C8	−158.8 (11)	C3—C2—C7—C6	−0.5 (9)
O1—Cu1—N1—C8	−3.7 (6)	C1—C2—C7—C6	174.4 (5)
N2—Cu1—N1—C8	179.2 (6)	C12—N1—C8—C9	−0.8 (10)
O3—Cu1—N1—C12	22.5 (16)	Cu1—N1—C8—C9	−179.4 (5)
O1—Cu1—N1—C12	177.6 (4)	N1—C8—C9—C10	0.7 (12)
N2—Cu1—N1—C12	0.5 (4)	C8—C9—C10—C11	−0.4 (13)
O3—Cu1—N2—C17	1.5 (6)	C9—C10—C11—C12	0.2 (11)
O1—Cu1—N2—C17	150.8 (17)	C9—C10—C11—C18	−177.4 (8)
N1—Cu1—N2—C17	178.2 (6)	C8—N1—C12—C13	−179.9 (6)
O3—Cu1—N2—C13	−176.5 (4)	Cu1—N1—C12—C13	−1.1 (7)
O1—Cu1—N2—C13	−27 (2)	C8—N1—C12—C11	0.6 (9)
N1—Cu1—N2—C13	0.2 (4)	Cu1—N1—C12—C11	179.5 (5)
O3—Cu1—O1—C1	−4.2 (6)	C10—C11—C12—N1	−0.3 (10)
N2—Cu1—O1—C1	−153.4 (17)	C18—C11—C12—N1	177.5 (6)
N1—Cu1—O1—C1	179.5 (5)	C10—C11—C12—C13	−179.8 (6)
O1—Cu1—O3—C3	7.2 (5)	C18—C11—C12—C13	−1.9 (10)
N2—Cu1—O3—C3	−176.0 (5)	C17—N2—C13—C14	0.1 (9)
N1—Cu1—O3—C3	162.2 (12)	Cu1—N2—C13—C14	178.4 (5)
Cu1—O1—C1—O2	−177.2 (4)	C17—N2—C13—C12	−179.1 (6)
Cu1—O1—C1—C2	2.0 (9)	Cu1—N2—C13—C12	−0.8 (7)
O2—C1—C2—C7	3.2 (9)	N1—C12—C13—N2	1.3 (8)
O1—C1—C2—C7	−176.1 (6)	C11—C12—C13—N2	−179.2 (6)
O2—C1—C2—C3	177.9 (6)	N1—C12—C13—C14	−178.0 (6)
O1—C1—C2—C3	−1.3 (9)	C11—C12—C13—C14	1.5 (10)
Cu1—O3—C3—C2	−8.9 (9)	N2—C13—C14—C15	−0.4 (10)
Cu1—O3—C3—C4	171.7 (4)	C12—C13—C14—C15	178.8 (6)
C7—C2—C3—O3	179.7 (6)	N2—C13—C14—C19	179.8 (6)
C1—C2—C3—O3	5.1 (9)	C12—C13—C14—C19	−1.0 (9)
C7—C2—C3—C4	−0.8 (8)	C13—C14—C15—C16	0.2 (11)
C1—C2—C3—C4	−175.5 (5)	C19—C14—C15—C16	179.9 (7)
O3—C3—C4—C5	−179.2 (6)	C14—C15—C16—C17	0.3 (11)
C2—C3—C4—C5	1.3 (9)	C13—N2—C17—C16	0.4 (10)
O3—C3—C4—Br1	−2.1 (7)	Cu1—N2—C17—C16	−177.5 (5)
C2—C3—C4—Br1	178.4 (4)	C15—C16—C17—N2	−0.7 (11)
C3—C4—C5—C6	−0.4 (10)	C10—C11—C18—C19	179.5 (7)
Br1—C4—C5—C6	−177.5 (4)	C12—C11—C18—C19	1.9 (11)
C4—C5—C6—C7	−0.9 (9)	C11—C18—C19—C14	−1.5 (12)
C4—C5—C6—Br2	177.0 (5)	C13—C14—C19—C18	1.0 (10)
C5—C6—C7—C2	1.4 (9)	C15—C14—C19—C18	−178.7 (7)
Br2—C6—C7—C2	−176.5 (5)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O4—H1···O2ⁱ	0.85	2.06	2.900 (8)	172
O4—H2···O2	0.85	2.10	2.932 (8)	166

Symmetry code: (i) x−1, y, z.

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