Dibromo­{4-bromo-2-[2-(isopropyl­amino)ethyl­imino­meth­yl]phenolato}zinc(II)

In the title mononuclear Schiff base zinc(II) complex, [ZnBr₂(C₁₂H₁₇BrN₂O)], the Zn^II ion is four-coordinated by one O atom and one imine N atom of a Schiff base ligand, and by two Br atoms, giving a tetra­hedral geometry. The crystal structure is stabilized by inter­molecular C—H...O hydrogen bonds.

Key indicators

• Single-crystal X-ray study
• T = 298 K
• Mean [sigma](C-C) = 0.013 Å
• R factor = 0.072
• wR factor = 0.215
• Data-to-parameter ratio = 19.9

checkCIF/PLATON results

No syntax errors found



Alert level B
PLAT232_ALERT_2_B Hirshfeld Test Diff (M-X)  Br3    -   Zn1     ..      34.66 su
PLAT242_ALERT_2_B Check Low       Ueq as Compared to Neighbors for        C10
PLAT432_ALERT_2_B Short Inter X...Y Contact  O1     ..  C10     ..       2.88 Ang.

Alert level C
PLAT029_ALERT_3_C _diffrn_measured_fraction_theta_full Low .......       0.98
PLAT062_ALERT_4_C Rescale T(min) & T(max) by .....................       0.90
PLAT125_ALERT_4_C No _symmetry_space_group_name_Hall Given .......          ?
PLAT220_ALERT_2_C Large Non-Solvent    C     Ueq(max)/Ueq(min) ...       2.89 Ratio
PLAT222_ALERT_3_C Large Non-Solvent    H     Ueq(max)/Ueq(min) ...       3.28 Ratio
PLAT241_ALERT_2_C Check High      Ueq as Compared to Neighbors for         N2
PLAT242_ALERT_2_C Check Low       Ueq as Compared to Neighbors for        Zn1
PLAT341_ALERT_3_C Low Bond Precision on C-C bonds (x 1000) Ang ...         13
PLAT420_ALERT_2_C D-H Without Acceptor       N2     -   H2A    ...          ?
PLAT420_ALERT_2_C D-H Without Acceptor       N2     -   H2B    ...          ?

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      0.905
            Tmax scaled      0.469 Tmin scaled      0.390

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

   0 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
   8 ALERT type 2 Indicator that the structure model may be wrong or deficient
   4 ALERT type 3 Indicator that the structure quality may be low
   2 ALERT type 4 Improvement, methodology, query or suggestion

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Computing details

Data collection: SMART (Bruker, 1998); cell refinement: SMART; data reduction: SAINT (Bruker, 1998); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: SHELXTL (Bruker, 1998); software used to prepare material for publication: SHELXTL.

Dibromo{4-bromo-2-[2-(isopropylamino)ethyliminomethyl]phenolato}zinc(II)

Crystal data

[ZnBr2(C12H17BrN2O)]	F(000) = 984
Mr = 510.38	Dx = 1.978 Mg m^−3
Monoclinic, P21/n	Mo Kα radiation, λ = 0.71073 Å
a = 7.044 (1) Å	Cell parameters from 3471 reflections
b = 15.048 (3) Å	θ = 2.5–24.1°
c = 16.179 (3) Å	µ = 8.42 mm^−1
β = 92.007 (3)°	T = 298 K
V = 1713.9 (5) Å^3	Block, colourless
Z = 4	0.12 × 0.10 × 0.09 mm

Data collection

Bruker SMART CCD area-detector diffractometer	3471 independent reflections
Radiation source: fine-focus sealed tube	2078 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.075
ω scans	θmax = 26.5°, θmin = 2.7°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −8→8
Tmin = 0.431, Tmax = 0.518	k = −18→18
13301 measured reflections	l = −19→20

Refinement

Refinement on F^2	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F^2 > 2σ(F^2)] = 0.072	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.215	H-atom parameters constrained
S = 1.05	w = 1/[σ^2(Fo^2) + (0.1122P)^2 + 0.0647P] where P = (Fo^2 + 2Fc^2)/3
3471 reflections	(Δ/σ)max < 0.001
174 parameters	Δρmax = 0.96 e Å^−3
0 restraints	Δρmin = −1.86 e Å^−3

Special details

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 (Ų)

	x	y	z	Uiso*/Ueq
Zn1	0.25285 (15)	0.75608 (7)	0.11034 (6)	0.0423 (3)
Br1	0.96561 (16)	0.50596 (7)	0.34194 (7)	0.0591 (4)
Br2	0.08996 (16)	0.88974 (8)	0.08763 (7)	0.0605 (4)
Br3	0.1238 (2)	0.63055 (12)	0.03592 (12)	0.1021 (6)
O1	0.3113 (9)	0.7391 (5)	0.2276 (4)	0.0503 (17)
N1	0.5261 (11)	0.7639 (5)	0.0798 (4)	0.0373 (17)
N2	0.6233 (14)	0.6740 (7)	−0.0823 (5)	0.065 (3)
H2A	0.7472	0.6807	−0.0682	0.078*
H2B	0.5739	0.6337	−0.0480	0.078*
C1	0.6198 (12)	0.6794 (6)	0.2021 (5)	0.0354 (19)
C2	0.4594 (12)	0.6908 (6)	0.2513 (5)	0.0362 (19)
C3	0.4646 (14)	0.6473 (7)	0.3284 (6)	0.049 (2)
H3	0.3621	0.6546	0.3624	0.059*
C4	0.6095 (14)	0.5958 (6)	0.3553 (6)	0.043 (2)
H4	0.6077	0.5694	0.4073	0.052*
C5	0.7633 (13)	0.5822 (6)	0.3044 (5)	0.041 (2)
C6	0.7725 (13)	0.6244 (6)	0.2311 (5)	0.040 (2)
H6	0.8790	0.6176	0.1993	0.048*
C7	0.6530 (13)	0.7261 (6)	0.1256 (5)	0.038 (2)
H7	0.7775	0.7286	0.1084	0.046*
C8	0.5845 (13)	0.8099 (6)	0.0040 (5)	0.042 (2)
H8A	0.7218	0.8151	0.0053	0.050*
H8B	0.5318	0.8694	0.0032	0.050*
C9	0.5210 (13)	0.7625 (6)	−0.0732 (5)	0.040 (2)
H9A	0.5455	0.7997	−0.1206	0.049*
H9B	0.3852	0.7521	−0.0723	0.049*
C10	0.6029 (14)	0.6412 (6)	−0.1701 (5)	0.041 (2)
H10	0.6599	0.6848	−0.2068	0.049*
C11	0.3994 (18)	0.6275 (8)	−0.1970 (7)	0.066 (3)
H11A	0.3918	0.6146	−0.2552	0.099*
H11B	0.3282	0.6803	−0.1862	0.099*
H11C	0.3480	0.5786	−0.1670	0.099*
C12	0.711 (3)	0.5550 (9)	−0.1752 (9)	0.101 (5)
H12A	0.7031	0.5236	−0.1238	0.151*
H12B	0.8415	0.5673	−0.1858	0.151*
H12C	0.6566	0.5194	−0.2192	0.151*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
Zn1	0.0337 (6)	0.0534 (7)	0.0401 (6)	0.0027 (5)	0.0062 (4)	−0.0014 (5)
Br1	0.0615 (7)	0.0521 (7)	0.0636 (7)	0.0165 (5)	0.0017 (5)	0.0092 (5)
Br2	0.0612 (7)	0.0585 (7)	0.0617 (7)	0.0133 (5)	−0.0014 (5)	−0.0009 (5)
Br3	0.0864 (11)	0.1016 (13)	0.1182 (14)	−0.0129 (9)	0.0040 (9)	0.0023 (10)
O1	0.044 (4)	0.068 (5)	0.040 (3)	0.014 (3)	0.014 (3)	−0.002 (3)
N1	0.047 (4)	0.037 (4)	0.029 (4)	−0.001 (3)	0.008 (3)	−0.001 (3)
N2	0.071 (6)	0.077 (7)	0.046 (5)	0.019 (5)	−0.001 (4)	−0.002 (5)
C1	0.038 (5)	0.038 (5)	0.030 (4)	0.003 (4)	0.008 (4)	−0.005 (4)
C2	0.030 (4)	0.045 (5)	0.034 (4)	0.005 (4)	0.009 (3)	0.000 (4)
C3	0.044 (5)	0.063 (7)	0.041 (5)	0.011 (5)	0.016 (4)	0.011 (5)
C4	0.053 (6)	0.043 (5)	0.035 (5)	−0.007 (4)	0.004 (4)	0.004 (4)
C5	0.042 (5)	0.039 (5)	0.043 (5)	−0.001 (4)	−0.001 (4)	0.000 (4)
C6	0.040 (5)	0.044 (5)	0.036 (5)	−0.001 (4)	0.011 (4)	0.001 (4)
C7	0.032 (5)	0.046 (5)	0.037 (5)	−0.001 (4)	0.010 (4)	−0.007 (4)
C8	0.046 (5)	0.043 (5)	0.037 (5)	0.000 (4)	0.008 (4)	0.004 (4)
C9	0.033 (5)	0.051 (6)	0.037 (5)	0.004 (4)	0.002 (4)	0.006 (4)
C10	0.059 (6)	0.038 (5)	0.026 (4)	0.002 (4)	0.011 (4)	0.002 (4)
C11	0.072 (8)	0.075 (8)	0.050 (6)	−0.014 (6)	0.001 (6)	−0.003 (5)
C12	0.165 (16)	0.068 (9)	0.071 (9)	0.052 (10)	0.021 (9)	−0.005 (7)

Geometric parameters (Å, º)

Zn1—O1	1.944 (7)	C4—H4	0.9300
Zn1—N1	2.007 (8)	C5—C6	1.349 (12)
Zn1—Br2	2.3382 (16)	C6—H6	0.9300
Zn1—Br3	2.402 (2)	C7—H7	0.9300
Br1—C5	1.912 (9)	C8—C9	1.493 (12)
O1—C2	1.317 (10)	C8—H8A	0.9700
N1—C7	1.275 (12)	C8—H8B	0.9700
N1—C8	1.479 (11)	C9—H9A	0.9700
N2—C10	1.506 (12)	C9—H9B	0.9700
N2—C9	1.524 (13)	C10—C11	1.498 (16)
N2—H2A	0.9000	C10—C12	1.507 (15)
N2—H2B	0.9000	C10—H10	0.9800
C1—C2	1.415 (11)	C11—H11A	0.9600
C1—C6	1.424 (13)	C11—H11B	0.9600
C1—C7	1.449 (12)	C11—H11C	0.9600
C2—C3	1.407 (12)	C12—H12A	0.9600
C3—C4	1.342 (14)	C12—H12B	0.9600
C3—H3	0.9300	C12—H12C	0.9600
C4—C5	1.399 (13)
O1—Zn1—N1	94.3 (3)	N1—C7—C1	125.5 (8)
O1—Zn1—Br2	110.6 (2)	N1—C7—H7	117.2
N1—Zn1—Br2	112.4 (2)	C1—C7—H7	117.2
O1—Zn1—Br3	116.7 (2)	N1—C8—C9	112.8 (8)
N1—Zn1—Br3	105.8 (2)	N1—C8—H8A	109.0
Br2—Zn1—Br3	115.01 (7)	C9—C8—H8A	109.0
C2—O1—Zn1	119.7 (5)	N1—C8—H8B	109.0
C7—N1—C8	118.7 (7)	C9—C8—H8B	109.0
C7—N1—Zn1	119.3 (6)	H8A—C8—H8B	107.8
C8—N1—Zn1	121.9 (6)	C8—C9—N2	111.7 (8)
C10—N2—C9	110.3 (7)	C8—C9—H9A	109.3
C10—N2—H2A	109.6	N2—C9—H9A	109.3
C9—N2—H2A	109.6	C8—C9—H9B	109.3
C10—N2—H2B	109.6	N2—C9—H9B	109.3
C9—N2—H2B	109.6	H9A—C9—H9B	107.9
H2A—N2—H2B	108.1	C11—C10—N2	112.2 (8)
C2—C1—C6	119.6 (8)	C11—C10—C12	110.1 (11)
C2—C1—C7	125.3 (8)	N2—C10—C12	107.6 (9)
C6—C1—C7	114.8 (7)	C11—C10—H10	109.0
O1—C2—C3	120.7 (7)	N2—C10—H10	109.0
O1—C2—C1	122.8 (8)	C12—C10—H10	109.0
C3—C2—C1	116.5 (8)	C10—C11—H11A	109.5
C4—C3—C2	123.5 (8)	C10—C11—H11B	109.5
C4—C3—H3	118.2	H11A—C11—H11B	109.5
C2—C3—H3	118.2	C10—C11—H11C	109.5
C3—C4—C5	119.2 (8)	H11A—C11—H11C	109.5
C3—C4—H4	120.4	H11B—C11—H11C	109.5
C5—C4—H4	120.4	C10—C12—H12A	109.5
C6—C5—C4	120.7 (9)	C10—C12—H12B	109.5
C6—C5—Br1	120.3 (7)	H12A—C12—H12B	109.5
C4—C5—Br1	118.9 (7)	C10—C12—H12C	109.5
C5—C6—C1	120.3 (8)	H12A—C12—H12C	109.5
C5—C6—H6	119.8	H12B—C12—H12C	109.5
C1—C6—H6	119.8

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
C10—H10···O1^i	0.98	1.91	2.882 (11)	170

Symmetry code: (i) x+1/2, −y+3/2, z−1/2.