Bis{2-bromo-4-chloro-6-[(2-pyridylmethyl­imino)meth­yl]phenolato}cadmium(II) methanol solvate monohydrate

The asymmetric unit of the title compound, [Cd(C₁₃H₉BrClN₂O)₂]·CH₃OH·H₂O, comprises a mononuclear cadmium(II) complex, a methanol mol­ecule and an uncoordinated water mol­ecule. The Cd^II atom is coordinated by two tridentate Schiff base ligands in a distorted octa­hedral geometry.

Key indicators

• Single-crystal X-ray study
• T = 298 K
• Mean [sigma](C-C) = 0.005 Å
• R factor = 0.032
• wR factor = 0.082
• Data-to-parameter ratio = 18.1

checkCIF/PLATON results

No syntax errors found



Alert level C
PLAT042_ALERT_1_C Calc. and Rep. MoietyFormula Strings Differ ....          ?
PLAT062_ALERT_4_C Rescale T(min) & T(max) by .....................       0.93
PLAT180_ALERT_3_C Check Cell Rounding: # of Values Ending with 0 =          3
PLAT480_ALERT_4_C Long H...A H-Bond Reported H3A    ..  BR1     ..       3.01 Ang.

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:   C27 H24 Br2 Cd1 Cl2 N4 O4
            Atom count from _chemical_formula_moiety:C27 H24 Br2 Cd1 Cl2 N4 O6
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      0.925
            Tmax scaled      0.514 Tmin scaled      0.447

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

   2 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
   0 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
   2 ALERT type 4 Improvement, methodology, query or suggestion
   0 ALERT type 5 Informative message, check

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Computing details

Data collection: SMART (Bruker, 1998); cell refinement: SAINT (Bruker, 1998); 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.

Bis{2-bromo-4-chloro-6-[(2-pyridylmethylimino)methyl]phenolato}cadmium(II) methanol monohydrate

Crystal data

[Cd(C13H9BrClN2O)2]·CH4O·H2O	F(000) = 1592
Mr = 811.62	Dx = 1.841 Mg m^−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 9086 reflections
a = 13.194 (1) Å	θ = 2.3–27.6°
b = 13.275 (1) Å	µ = 3.70 mm^−1
c = 17.951 (2) Å	T = 298 K
β = 111.33 (1)°	Block, colourless
V = 2928.8 (5) Å^3	0.23 × 0.22 × 0.18 mm
Z = 4

Data collection

Bruker CCD area-detector diffractometer	6673 independent reflections
Radiation source: fine-focus sealed tube	5514 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.026
ω scans	θmax = 27.5°, θmin = 1.7°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −17→17
Tmin = 0.484, Tmax = 0.556	k = −17→17
24866 measured reflections	l = −23→22

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)] = 0.032	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.082	H atoms treated by a mixture of independent and constrained refinement
S = 1.03	w = 1/[σ^2(Fo^2) + (0.0448P)^2 + 1.1396P] where P = (Fo^2 + 2Fc^2)/3
6673 reflections	(Δ/σ)max < 0.001
369 parameters	Δρmax = 0.85 e Å^−3
3 restraints	Δρmin = −0.59 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
Cd1	0.233166 (15)	0.567322 (14)	0.369000 (12)	0.03446 (7)
Br1	0.10993 (4)	0.60162 (3)	0.06851 (2)	0.07010 (12)
Br2	0.49719 (3)	0.85735 (2)	0.37114 (2)	0.05471 (10)
Cl1	0.20543 (7)	0.20356 (7)	0.03716 (5)	0.0603 (2)
Cl2	0.17614 (9)	1.13853 (6)	0.33546 (9)	0.0860 (4)
O1	0.2174 (2)	0.55219 (15)	0.24188 (13)	0.0502 (5)
O2	0.31958 (16)	0.71657 (13)	0.37761 (13)	0.0433 (5)
O3	0.3425 (2)	0.7055 (2)	0.21799 (15)	0.0630 (6)
O4	0.4946 (2)	0.6629 (2)	0.14987 (17)	0.0735 (7)
H4	0.4553	0.6737	0.1754	0.110*
N1	0.32945 (18)	0.41733 (16)	0.37496 (14)	0.0358 (5)
N2	0.32982 (18)	0.52872 (17)	0.50364 (14)	0.0374 (5)
N3	0.10608 (19)	0.67582 (17)	0.38743 (16)	0.0412 (5)
N4	0.07278 (19)	0.47286 (17)	0.35648 (15)	0.0417 (5)
C1	0.2674 (2)	0.3791 (2)	0.23216 (18)	0.0399 (6)
C2	0.2185 (2)	0.4738 (2)	0.19989 (18)	0.0414 (6)
C3	0.1726 (3)	0.4779 (2)	0.11556 (19)	0.0480 (7)
C4	0.1698 (3)	0.3977 (3)	0.0656 (2)	0.0516 (8)
H4A	0.1384	0.4045	0.0104	0.062*
C5	0.2153 (2)	0.3067 (2)	0.10016 (19)	0.0468 (7)
C6	0.2639 (2)	0.2981 (2)	0.18046 (19)	0.0449 (7)
H6	0.2960	0.2372	0.2022	0.054*
C7	0.3248 (2)	0.3600 (2)	0.31633 (18)	0.0390 (6)
H7	0.3626	0.2994	0.3294	0.047*
C8	0.3948 (2)	0.3799 (2)	0.45432 (18)	0.0396 (6)
H8A	0.4691	0.3710	0.4574	0.047*
H8B	0.3673	0.3143	0.4617	0.047*
C9	0.3946 (2)	0.44835 (19)	0.52139 (17)	0.0359 (6)
C10	0.4590 (2)	0.4248 (2)	0.59931 (19)	0.0449 (7)
H10	0.5040	0.3685	0.6104	0.054*
C11	0.4554 (3)	0.4860 (3)	0.6603 (2)	0.0515 (8)
H11	0.4980	0.4712	0.7132	0.062*
C12	0.3883 (3)	0.5693 (2)	0.6425 (2)	0.0501 (7)
H12	0.3841	0.6114	0.6827	0.060*
C13	0.3282 (2)	0.5882 (2)	0.56394 (19)	0.0447 (7)
H13	0.2840	0.6450	0.5515	0.054*
C14	0.1815 (2)	0.83884 (19)	0.37023 (17)	0.0376 (6)
C15	0.2857 (2)	0.80791 (19)	0.37109 (16)	0.0352 (6)
C16	0.3534 (2)	0.8885 (2)	0.36373 (18)	0.0412 (6)
C17	0.3212 (3)	0.9877 (2)	0.3522 (2)	0.0496 (7)
H17	0.3675	1.0370	0.3458	0.060*
C18	0.2182 (3)	1.0124 (2)	0.3503 (2)	0.0522 (8)
C19	0.1506 (3)	0.9408 (2)	0.3603 (2)	0.0464 (7)
H19	0.0829	0.9596	0.3607	0.056*
C20	0.1011 (2)	0.7716 (2)	0.37952 (17)	0.0390 (6)
H20	0.0376	0.8017	0.3798	0.047*
C21	0.0135 (3)	0.6287 (2)	0.4000 (2)	0.0554 (9)
H21A	−0.0516	0.6672	0.3714	0.067*
H21B	0.0250	0.6316	0.4565	0.067*
C22	−0.0050 (2)	0.5203 (2)	0.37272 (18)	0.0423 (6)
C23	−0.1009 (3)	0.4724 (3)	0.3669 (2)	0.0590 (9)
H23	−0.1553	0.5075	0.3774	0.071*
C24	−0.1150 (3)	0.3719 (3)	0.3453 (2)	0.0585 (9)
H24	−0.1784	0.3381	0.3417	0.070*
C25	−0.0338 (3)	0.3232 (2)	0.3293 (2)	0.0504 (7)
H25	−0.0407	0.2555	0.3151	0.061*
C26	0.0572 (2)	0.3754 (2)	0.3346 (2)	0.0474 (7)
H26	0.1113	0.3421	0.3226	0.057*
C27	0.4303 (4)	0.6405 (3)	0.0706 (3)	0.0818 (12)
H27A	0.3944	0.7006	0.0443	0.123*
H27B	0.3769	0.5910	0.0697	0.123*
H27C	0.4755	0.6146	0.0435	0.123*
H3B	0.373 (3)	0.721 (3)	0.2673 (9)	0.080*
H3A	0.297 (3)	0.660 (2)	0.217 (2)	0.080*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
Cd1	0.03619 (11)	0.02645 (10)	0.04439 (12)	0.00293 (7)	0.01900 (9)	0.00242 (8)
Br1	0.0838 (3)	0.0609 (2)	0.0539 (2)	0.0197 (2)	0.01102 (19)	0.00636 (17)
Br2	0.04390 (17)	0.04346 (18)	0.0816 (3)	−0.00345 (13)	0.02861 (17)	0.00118 (15)
Cl1	0.0662 (5)	0.0616 (5)	0.0629 (5)	−0.0012 (4)	0.0351 (4)	−0.0239 (4)
Cl2	0.0908 (7)	0.0250 (4)	0.1596 (11)	0.0130 (4)	0.0662 (8)	0.0136 (5)
O1	0.0739 (15)	0.0334 (11)	0.0479 (12)	0.0059 (10)	0.0278 (11)	0.0022 (9)
O2	0.0417 (11)	0.0263 (9)	0.0662 (13)	0.0026 (8)	0.0249 (10)	0.0030 (9)
O3	0.0745 (17)	0.0605 (16)	0.0609 (15)	−0.0129 (12)	0.0329 (14)	−0.0044 (12)
O4	0.0658 (16)	0.0825 (19)	0.0741 (18)	0.0062 (14)	0.0279 (14)	−0.0081 (15)
N1	0.0358 (12)	0.0304 (11)	0.0441 (13)	0.0002 (9)	0.0182 (10)	0.0005 (10)
N2	0.0375 (12)	0.0336 (11)	0.0440 (13)	0.0017 (9)	0.0182 (10)	0.0026 (10)
N3	0.0404 (12)	0.0305 (11)	0.0603 (16)	−0.0011 (10)	0.0275 (12)	−0.0018 (11)
N4	0.0377 (13)	0.0334 (12)	0.0572 (15)	0.0006 (10)	0.0211 (11)	0.0037 (11)
C1	0.0416 (15)	0.0362 (15)	0.0476 (17)	−0.0015 (12)	0.0230 (13)	−0.0032 (12)
C2	0.0433 (15)	0.0392 (15)	0.0463 (17)	0.0005 (12)	0.0219 (13)	−0.0002 (13)
C3	0.0469 (17)	0.0495 (18)	0.0478 (17)	0.0063 (14)	0.0174 (14)	0.0037 (14)
C4	0.0456 (17)	0.064 (2)	0.0457 (18)	0.0034 (15)	0.0165 (14)	−0.0084 (15)
C5	0.0445 (16)	0.0515 (18)	0.0506 (18)	−0.0035 (13)	0.0246 (14)	−0.0142 (14)
C6	0.0452 (16)	0.0400 (16)	0.0574 (19)	−0.0015 (12)	0.0281 (15)	−0.0049 (13)
C7	0.0382 (14)	0.0307 (13)	0.0529 (17)	0.0005 (11)	0.0223 (13)	0.0004 (12)
C8	0.0396 (15)	0.0306 (13)	0.0520 (17)	0.0056 (11)	0.0208 (13)	0.0039 (12)
C9	0.0334 (13)	0.0308 (13)	0.0459 (15)	−0.0024 (10)	0.0172 (12)	0.0049 (11)
C10	0.0411 (16)	0.0360 (15)	0.0529 (18)	0.0023 (12)	0.0116 (14)	0.0040 (13)
C11	0.0512 (18)	0.0532 (19)	0.0450 (17)	−0.0016 (15)	0.0113 (14)	0.0022 (14)
C12	0.0511 (18)	0.0524 (18)	0.0478 (18)	−0.0022 (14)	0.0193 (15)	−0.0086 (14)
C13	0.0419 (16)	0.0416 (16)	0.0530 (18)	0.0038 (12)	0.0203 (14)	−0.0031 (13)
C14	0.0442 (15)	0.0281 (13)	0.0435 (15)	0.0007 (11)	0.0196 (13)	−0.0011 (11)
C15	0.0401 (14)	0.0273 (13)	0.0397 (14)	0.0010 (11)	0.0164 (12)	0.0004 (10)
C16	0.0382 (15)	0.0348 (14)	0.0541 (18)	−0.0019 (11)	0.0211 (13)	−0.0012 (13)
C17	0.0545 (18)	0.0318 (15)	0.067 (2)	−0.0059 (13)	0.0279 (16)	0.0020 (14)
C18	0.063 (2)	0.0238 (14)	0.075 (2)	0.0044 (13)	0.0308 (18)	0.0025 (13)
C19	0.0506 (17)	0.0318 (14)	0.062 (2)	0.0048 (12)	0.0274 (15)	0.0003 (13)
C20	0.0363 (14)	0.0331 (14)	0.0511 (17)	0.0046 (11)	0.0198 (13)	−0.0040 (12)
C21	0.0543 (19)	0.0394 (16)	0.091 (3)	−0.0053 (14)	0.0480 (19)	−0.0057 (16)
C22	0.0387 (15)	0.0372 (15)	0.0543 (18)	−0.0023 (12)	0.0210 (13)	0.0035 (13)
C23	0.0454 (18)	0.0511 (19)	0.092 (3)	−0.0046 (15)	0.0386 (19)	−0.0022 (18)
C24	0.0475 (18)	0.0493 (19)	0.084 (3)	−0.0134 (15)	0.0308 (18)	−0.0004 (17)
C25	0.0530 (18)	0.0369 (15)	0.062 (2)	−0.0072 (13)	0.0210 (16)	−0.0017 (14)
C26	0.0432 (16)	0.0372 (15)	0.066 (2)	0.0007 (12)	0.0243 (15)	−0.0002 (14)
C27	0.090 (3)	0.081 (3)	0.065 (3)	0.017 (2)	0.018 (2)	0.004 (2)

Geometric parameters (Å, º)

Cd1—O1	2.224 (2)	C8—H8A	0.9700
Cd1—O2	2.263 (2)	C8—H8B	0.9700
Cd1—N3	2.323 (2)	C9—C10	1.383 (4)
Cd1—N2	2.343 (2)	C10—C11	1.378 (5)
Cd1—N1	2.343 (2)	C10—H10	0.9300
Cd1—N4	2.399 (2)	C11—C12	1.380 (5)
Br1—C3	1.894 (3)	C11—H11	0.9300
Br2—C16	1.898 (3)	C12—C13	1.367 (5)
Cl1—C5	1.750 (3)	C12—H12	0.9300
Cl2—C18	1.753 (3)	C13—H13	0.9300
O1—C2	1.288 (3)	C14—C19	1.406 (4)
O2—C15	1.283 (3)	C14—C15	1.430 (4)
O3—H3B	0.854 (10)	C14—C20	1.442 (4)
O3—H3A	0.85 (3)	C15—C16	1.430 (4)
O4—C27	1.397 (5)	C16—C17	1.376 (4)
O4—H4	0.8200	C17—C18	1.386 (4)
N1—C7	1.282 (4)	C17—H17	0.9300
N1—C8	1.458 (4)	C18—C19	1.360 (4)
N2—C9	1.331 (3)	C19—H19	0.9300
N2—C13	1.346 (4)	C20—H20	0.9300
N3—C20	1.279 (3)	C21—C22	1.511 (4)
N3—C21	1.462 (4)	C21—H21A	0.9700
N4—C22	1.324 (4)	C21—H21B	0.9700
N4—C26	1.346 (4)	C22—C23	1.386 (4)
C1—C6	1.410 (4)	C23—C24	1.383 (5)
C1—C2	1.435 (4)	C23—H23	0.9300
C1—C7	1.445 (4)	C24—C25	1.368 (5)
C2—C3	1.412 (4)	C24—H24	0.9300
C3—C4	1.383 (4)	C25—C26	1.358 (4)
C4—C5	1.390 (5)	C25—H25	0.9300
C4—H4A	0.9300	C26—H26	0.9300
C5—C6	1.353 (5)	C27—H27A	0.9600
C6—H6	0.9300	C27—H27B	0.9600
C7—H7	0.9300	C27—H27C	0.9600
C8—C9	1.509 (4)
O1—Cd1—O2	90.35 (8)	C11—C10—C9	119.0 (3)
O1—Cd1—N3	113.51 (9)	C11—C10—H10	120.5
O2—Cd1—N3	79.59 (7)	C9—C10—H10	120.5
O1—Cd1—N2	148.39 (8)	C10—C11—C12	119.5 (3)
O2—Cd1—N2	92.83 (8)	C10—C11—H11	120.2
N3—Cd1—N2	97.99 (9)	C12—C11—H11	120.2
O1—Cd1—N1	79.46 (8)	C13—C12—C11	117.9 (3)
O2—Cd1—N1	119.31 (8)	C13—C12—H12	121.0
N3—Cd1—N1	158.05 (8)	C11—C12—H12	121.0
N2—Cd1—N1	71.60 (8)	N2—C13—C12	123.4 (3)
O1—Cd1—N4	96.10 (9)	N2—C13—H13	118.3
O2—Cd1—N4	150.38 (7)	C12—C13—H13	118.3
N3—Cd1—N4	71.32 (8)	C19—C14—C15	120.8 (3)
N2—Cd1—N4	96.48 (9)	C19—C14—C20	114.8 (3)
N1—Cd1—N4	90.30 (8)	C15—C14—C20	124.5 (2)
C2—O1—Cd1	131.04 (18)	O2—C15—C14	125.0 (2)
C15—O2—Cd1	132.17 (17)	O2—C15—C16	120.5 (2)
H3B—O3—H3A	105 (2)	C14—C15—C16	114.5 (2)
C27—O4—H4	109.5	C17—C16—C15	124.1 (3)
C7—N1—C8	115.7 (2)	C17—C16—Br2	117.7 (2)
C7—N1—Cd1	127.1 (2)	C15—C16—Br2	118.2 (2)
C8—N1—Cd1	116.89 (17)	C16—C17—C18	118.4 (3)
C9—N2—C13	118.3 (3)	C16—C17—H17	120.8
C9—N2—Cd1	118.91 (19)	C18—C17—H17	120.8
C13—N2—Cd1	122.67 (19)	C19—C18—C17	121.1 (3)
C20—N3—C21	115.5 (2)	C19—C18—Cl2	120.1 (2)
C20—N3—Cd1	127.68 (19)	C17—C18—Cl2	118.9 (2)
C21—N3—Cd1	116.37 (17)	C18—C19—C14	121.0 (3)
C22—N4—C26	118.2 (2)	C18—C19—H19	119.5
C22—N4—Cd1	117.30 (18)	C14—C19—H19	119.5
C26—N4—Cd1	124.48 (19)	N3—C20—C14	128.2 (3)
C6—C1—C2	120.0 (3)	N3—C20—H20	115.9
C6—C1—C7	115.7 (3)	C14—C20—H20	115.9
C2—C1—C7	124.3 (3)	N3—C21—C22	113.7 (2)
O1—C2—C3	120.3 (3)	N3—C21—H21A	108.8
O1—C2—C1	124.8 (3)	C22—C21—H21A	108.8
C3—C2—C1	114.9 (3)	N3—C21—H21B	108.8
C4—C3—C2	124.4 (3)	C22—C21—H21B	108.8
C4—C3—Br1	118.3 (2)	H21A—C21—H21B	107.7
C2—C3—Br1	117.3 (2)	N4—C22—C23	121.7 (3)
C3—C4—C5	118.3 (3)	N4—C22—C21	118.6 (2)
C3—C4—H4A	120.9	C23—C22—C21	119.7 (3)
C5—C4—H4A	120.9	C24—C23—C22	119.3 (3)
C6—C5—C4	120.6 (3)	C24—C23—H23	120.3
C6—C5—Cl1	121.2 (3)	C22—C23—H23	120.3
C4—C5—Cl1	118.2 (2)	C25—C24—C23	118.6 (3)
C5—C6—C1	121.8 (3)	C25—C24—H24	120.7
C5—C6—H6	119.1	C23—C24—H24	120.7
C1—C6—H6	119.1	C26—C25—C24	119.0 (3)
N1—C7—C1	127.2 (3)	C26—C25—H25	120.5
N1—C7—H7	116.4	C24—C25—H25	120.5
C1—C7—H7	116.4	N4—C26—C25	123.2 (3)
N1—C8—C9	113.7 (2)	N4—C26—H26	118.4
N1—C8—H8A	108.8	C25—C26—H26	118.4
C9—C8—H8A	108.8	O4—C27—H27A	109.5
N1—C8—H8B	108.8	O4—C27—H27B	109.5
C9—C8—H8B	108.8	H27A—C27—H27B	109.5
H8A—C8—H8B	107.7	O4—C27—H27C	109.5
N2—C9—C10	121.9 (3)	H27A—C27—H27C	109.5
N2—C9—C8	118.6 (2)	H27B—C27—H27C	109.5
C10—C9—C8	119.5 (2)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
O3—H3A···Br1	0.85 (3)	3.01 (3)	3.540 (3)	123 (3)
O3—H3A···O1	0.85 (3)	1.92 (3)	2.752 (3)	166 (4)
O3—H3B···Br2	0.85 (1)	2.68 (2)	3.421 (3)	145 (3)
O3—H3B···O2	0.85 (1)	2.33 (3)	2.992 (3)	134 (3)
O4—H4···O3	0.82	1.95	2.762 (4)	170