Redetermination of (2,2′-bipyridyl-κ²N,N′)chloro­(glycinato-κ²N:O)copper(II) dihydrate

The redetermined structure of the title compound, [Cu(C₂H₄NO₂)Cl(C₁₀H₈N₂)]·2H₂O, confirms that reported earlier [Neitzel & Desiderato (1975). Cryst. Struct. Commun. 4, 333–336] with respect to the non-H atoms. All the H atoms have been located in the present study and the network of N—H...O, N—H...Cl, O—H...O and O—H...Cl hydrogen bonds has been elucidated.

Key indicators

• Single-crystal X-ray study
• T = 123 K
• Mean [sigma](C-C) = 0.005 Å
• R factor = 0.030
• wR factor = 0.086
• Data-to-parameter ratio = 16.0

checkCIF/PLATON results

No syntax errors found



Alert level B
PLAT417_ALERT_2_B Short Inter D-H..H-D       H10    ..  H13     ..       1.89 Ang.

Alert level C
PLAT042_ALERT_1_C Calc. and Rep. MoietyFormula Strings Differ ....          ?
PLAT066_ALERT_1_C Predicted and Reported Transmissions Identical .          ?
PLAT232_ALERT_2_C Hirshfeld Test Diff (M-X)  Cu1    -   Cl1     ..       7.86 su
PLAT432_ALERT_2_C Short Inter X...Y Contact  O1     ..  C12     ..       3.00 Ang.

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

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

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Computing details

Data collection: RAPID-AUTO (Rigaku, 2003); cell refinement: RAPID-AUTO; data reduction: CrystalStructure (Rigaku/MSC, 2004) and CRYSTALS (Watkin et al., 1996); program(s) used to solve structure: SIR97 (Altomare et al., 1999) and DIRDIF99 (Beurskens et al., 1999); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEP-3 (Farrugia, 1997); software used to prepare material for publication: CrystalStructure.

(2,2'-bipyridyl-κ²N,N')chloro(glycinato-κ²N:O)copper(II) dihydrate

Crystal data

[Cu(C2H4NO2)Cl(C10H8N2)]·2H2O	F(000) = 748.00
Mr = 365.28	Dx = 1.704 Mg m^−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.7107 Å
Hall symbol: -P 2ybc	Cell parameters from 10955 reflections
a = 10.47 (2) Å	θ = 3.0–27.5°
b = 18.32 (2) Å	µ = 1.74 mm^−1
c = 7.646 (9) Å	T = 123 K
β = 103.92 (5)°	Prism, blue
V = 1424 (4) Å^3	0.30 × 0.10 × 0.05 mm
Z = 4

Data collection

Rigaku R-AXIS RAPID diffractometer	2104 reflections with F^2 > 2σ(F^2)
Detector resolution: 10.00 pixels mm^-1	Rint = 0.032
ω scans	θmax = 27.5°
Absorption correction: multi-scan (ABSCOR; Higashi, 1995)	h = −13→13
Tmin = 0.812, Tmax = 0.917	k = −23→23
13847 measured reflections	l = −9→9
3249 independent reflections

Refinement

Refinement on F^2	All H-atom parameters refined
R[F^2 > 2σ(F^2)] = 0.030	w = 1/[σ^2(Fo^2) + (0.0561P)^2] where P = (Fo^2 + 2Fc^2)/3
wR(F^2) = 0.086	(Δ/σ)max < 0.001
S = 0.94	Δρmax = 0.40 e Å^−3
3249 reflections	Δρmin = −0.63 e Å^−3
203 parameters

Special details

Refinement. Refinement using all reflections. The weighted R-factor (wR) and goodness of fit (S) are based on F². R-factor (gt) are based on F. The threshold expression of F² > 2.0 σ(F²) is used only for calculating R-factor (gt).

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Ų)

	x	y	z	Uiso*/Ueq
Cu1	0.36217 (3)	0.41535 (1)	0.66617 (4)	0.0188 (1)
Cl1	0.44017 (7)	0.32463 (3)	0.93870 (9)	0.0242 (1)
O1	0.5175 (2)	0.47853 (9)	0.7139 (2)	0.0210 (4)
O2	0.7169 (2)	0.4906 (1)	0.6620 (3)	0.0274 (4)
O3	0.2231 (3)	0.1196 (1)	0.6391 (3)	0.0384 (5)
O4	0.6476 (3)	0.2411 (1)	0.7784 (4)	0.0500 (6)
N1	0.1863 (2)	0.3667 (1)	0.5909 (3)	0.0195 (4)
N2	0.2578 (2)	0.4859 (1)	0.7751 (3)	0.0171 (4)
N3	0.4536 (2)	0.3621 (1)	0.5020 (3)	0.0220 (5)
C1	0.1598 (3)	0.3029 (1)	0.5042 (4)	0.0251 (6)
C2	0.0341 (3)	0.2738 (1)	0.4580 (4)	0.0256 (6)
C3	−0.0681 (3)	0.3118 (1)	0.5013 (4)	0.0261 (6)
C4	−0.0415 (3)	0.3776 (1)	0.5929 (4)	0.0211 (5)
C5	0.0867 (3)	0.4035 (1)	0.6360 (3)	0.0171 (5)
C6	0.1276 (3)	0.4722 (1)	0.7371 (3)	0.0173 (5)
C7	0.0401 (3)	0.5189 (1)	0.7915 (3)	0.0199 (5)
C8	0.0893 (3)	0.5811 (1)	0.8882 (4)	0.0226 (5)
C9	0.2229 (3)	0.5944 (1)	0.9292 (4)	0.0227 (5)
C10	0.3050 (3)	0.5453 (1)	0.8704 (3)	0.0201 (5)
C11	0.5918 (3)	0.3864 (1)	0.5405 (4)	0.0277 (6)
C12	0.6111 (3)	0.4575 (1)	0.6460 (4)	0.0222 (5)
H1	0.2281	0.2773	0.4741	0.030*
H2	0.0187	0.2292	0.3984	0.031*
H3	−0.1534	0.2935	0.4696	0.031*
H4	−0.1086	0.4038	0.6249	0.025*
H5	−0.0496	0.5088	0.7637	0.024*
H6	0.0326	0.6135	0.9251	0.027*
H7	0.2576	0.6355	0.9952	0.027*
H8	0.3952	0.5541	0.8980	0.024*
H9	0.4501	0.3136	0.5200	0.026*
H10	0.4135	0.3716	0.3863	0.026*
H11	0.6178	0.3931	0.4280	0.033*
H12	0.6479	0.3490	0.6093	0.033*
H13	0.2743	0.0838	0.7156	0.058*
H14	0.2887	0.1294	0.5748	0.058*
H15	0.5791	0.2630	0.8314	0.075*
H16	0.5937	0.2025	0.7059	0.075*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
Cu1	0.0101 (2)	0.0201 (2)	0.0273 (2)	0.0000 (1)	0.0065 (1)	−0.0020 (1)
Cl1	0.0220 (4)	0.0210 (3)	0.0302 (4)	0.0014 (2)	0.0074 (3)	0.0036 (2)
O1	0.013 (1)	0.0242 (9)	0.027 (1)	−0.0016 (7)	0.0062 (8)	−0.0017 (7)
O2	0.014 (1)	0.032 (1)	0.038 (1)	−0.0016 (8)	0.0098 (9)	0.0003 (8)
O3	0.038 (1)	0.036 (1)	0.048 (1)	−0.002 (1)	0.024 (1)	0.0018 (9)
O4	0.045 (2)	0.049 (1)	0.055 (2)	0.007 (1)	0.011 (1)	0.003 (1)
N1	0.015 (1)	0.021 (1)	0.023 (1)	0.0002 (8)	0.0054 (9)	0.0010 (8)
N2	0.012 (1)	0.020 (1)	0.019 (1)	0.0008 (8)	0.0051 (9)	0.0021 (7)
N3	0.017 (1)	0.022 (1)	0.028 (1)	0.0029 (8)	0.008 (1)	−0.0008 (8)
C1	0.022 (2)	0.022 (1)	0.033 (2)	0.000 (1)	0.008 (1)	−0.004 (1)
C2	0.023 (2)	0.025 (1)	0.028 (2)	−0.006 (1)	0.006 (1)	−0.004 (1)
C3	0.017 (2)	0.028 (1)	0.031 (2)	−0.006 (1)	0.002 (1)	0.002 (1)
C4	0.014 (1)	0.024 (1)	0.025 (1)	0.002 (1)	0.004 (1)	0.0026 (9)
C5	0.014 (1)	0.019 (1)	0.018 (1)	0.0016 (9)	0.004 (1)	0.0049 (8)
C6	0.013 (1)	0.019 (1)	0.021 (1)	0.0010 (9)	0.006 (1)	0.0055 (9)
C7	0.014 (1)	0.022 (1)	0.026 (1)	0.0019 (9)	0.008 (1)	0.0039 (9)
C8	0.021 (1)	0.023 (1)	0.026 (1)	0.004 (1)	0.011 (1)	0.002 (1)
C9	0.024 (2)	0.021 (1)	0.026 (1)	−0.001 (1)	0.010 (1)	−0.0006 (9)
C10	0.014 (1)	0.024 (1)	0.023 (1)	−0.003 (1)	0.005 (1)	0.0002 (9)
C11	0.019 (2)	0.026 (1)	0.042 (2)	0.001 (1)	0.015 (1)	−0.002 (1)
C12	0.016 (1)	0.023 (1)	0.028 (1)	0.002 (1)	0.006 (1)	0.002 (1)

Geometric parameters (Å, º)

Cu1—O1	1.957 (2)	C1—H1	0.9300
Cu1—N1	2.002 (2)	C2—C3	1.382 (4)
Cu1—N2	1.999 (2)	C2—H2	0.9300
Cu1—N3	2.006 (2)	C3—C4	1.388 (4)
Cu1—Cl1	2.637 (5)	C3—H3	0.9301
O1—C12	1.274 (4)	C4—C5	1.387 (4)
O2—C12	1.242 (3)	C4—H4	0.9300
O3—H13	0.9534	C5—C6	1.485 (3)
O3—H14	0.9532	C6—C7	1.389 (4)
O4—H15	0.9889	C7—C8	1.387 (3)
O4—H16	0.9881	C7—H5	0.9300
N1—C1	1.338 (3)	C8—C9	1.380 (4)
N1—C5	1.354 (4)	C8—H6	0.9300
N2—C6	1.347 (3)	C9—C10	1.391 (4)
N2—C10	1.337 (3)	C9—H7	0.9300
N3—C11	1.474 (4)	C10—H8	0.9300
N3—H9	0.9000	C11—C12	1.520 (4)
N3—H10	0.9000	C11—H11	0.9700
C1—C2	1.384 (4)	C11—H12	0.9701
Cl1—Cu1—O1	98.04 (5)	C3—C2—H2	120.4028
Cl1—Cu1—N1	92.01 (6)	H2—C2—C1	120.3945
Cl1—Cu1—N2	100.04 (6)	C4—C3—C2	119.0 (3)
Cl1—Cu1—N3	94.83 (6)	C4—C3—H3	120.4850
O1—Cu1—N1	169.25 (7)	H3—C3—C2	120.4663
O1—Cu1—N2	93.04 (8)	C5—C4—C3	118.8 (3)
O1—Cu1—N3	84.52 (9)	C5—C4—H4	120.6092
N1—Cu1—N2	81.40 (9)	H4—C4—C3	120.6090
N1—Cu1—N3	98.49 (9)	C6—C5—N1	114.3 (2)
N2—Cu1—N3	165.12 (8)	C6—C5—C4	123.7 (2)
C12—O1—Cu1	115.5 (2)	C7—C6—N2	121.7 (2)
H13—O3—H14	94.4521	C7—C6—C5	123.4 (2)
H15—O4—H16	98.4485	C8—C7—C6	118.6 (2)
C1—N1—Cu1	126.7 (2)	C8—C7—H5	120.7078
C1—N1—C5	118.7 (2)	H5—C7—C6	120.6904
C5—N1—Cu1	114.6 (1)	C9—C8—C7	119.5 (3)
C6—N2—Cu1	114.5 (2)	C9—C8—H6	120.2661
C6—N2—C10	119.5 (2)	H6—C8—C7	120.2513
C10—N2—Cu1	125.8 (2)	C10—C9—C8	118.9 (2)
C11—N3—Cu1	108.7 (2)	C10—C9—H7	120.5407
C11—N3—H9	109.9502	H7—C9—C8	120.5300
C11—N3—H10	109.9469	H8—C10—N2	119.1351
H9—N3—Cu1	109.9404	H8—C10—C9	119.1298
H9—N3—H10	108.3329	C12—C11—N3	111.3 (2)
H10—N3—Cu1	109.9417	C12—C11—H12	109.3690
C2—C1—N1	122.3 (3)	C12—C11—H11	109.3656
C2—C1—H1	118.8732	H11—C11—N3	109.3685
H1—C1—N1	118.8691	H11—C11—H12	107.9880
C3—C2—C1	119.2 (2)	H12—C11—N3	109.3679
Cl1—Cu1—O1—C12	86.7 (2)	C1—C2—C3—C4	−1.1 (4)
Cl1—Cu1—N1—C1	−76.2 (2)	C2—C3—C4—C5	0.8 (4)
Cl1—Cu1—N2—C6	−95.5 (2)	C3—C4—C5—N1	0.2 (4)
Cl1—Cu1—N3—C11	−84.1 (2)	N1—C5—C6—N2	−2.7 (3)
Cu1—O1—C12—O2	179.9 (2)	C4—C5—C6—N2	176.2 (2)
Cu1—O1—C12—C11	−1.0 (3)	N2—C6—C7—C8	−0.3 (4)
Cu1—N1—C1—C2	−180.0 (2)	C6—C7—C8—C9	−0.7 (4)
Cu1—N1—C5—C4	179.6 (2)	C7—C8—C9—C10	0.8 (4)
Cu1—N2—C6—C5	5.5 (3)	C8—C9—C10—N2	0.1 (3)
Cu1—N2—C10—C9	174.9 (2)	N3—C11—C12—O1	12.6 (3)
Cu1—N3—C11—C12	−17.0 (3)	N3—C11—C12—O2	−168.3 (2)
N1—C1—C2—C3	0.4 (4)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
N3—H9···Cl1^i	0.90	2.60	3.453 (7)	157
N3—H10···O3^i	0.90	2.40	3.227 (7)	153
O3—H13···O2^ii	0.95	1.94	2.799 (3)	148
O3—H14···Cl1^i	0.95	2.26	3.199 (7)	168
O4—H15···Cl1	0.99	2.15	3.137 (7)	172
O4—H16···Cl1^i	0.99	2.33	3.194 (7)	145

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