{2-[(2-Carbamoylhydrazin-1-yl­idene)methyl-κ2N1,O]-5-meth­oxy­phenolato-κO1}chloridocopper(II)

Kunnath, R.J.; Prathapachandra Kurup, M.R.; Ng, S.W.

doi:10.1107/S160053681203574X

{2-[(2-Carbamoylhydrazin-1-ylidene)methyl-κ²N¹,O]-5-methoxyphenolato-κO¹}chloridocopper(II)

R. J. Kunnath, M. R. Prathapachandra Kurup and S. W. Ng

The asymmetric unit of the title compound, [Cu(C₉H₁₀N₃O₃)Cl], contains two independent molecules with similar structures. The Cu^II cation is N,O,O′-chelated by the deprotonated Schiff base ligand and is further coordinated by a Cl⁻ anion in a distorted ClNO₂ square-planar geometry. In the crystal, adjacent molecules are linked by N—H

O and N—H

Cl hydrogen bonds, forming a two-dimensional network parallel to [100].

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Supporting information

	Crystallographic Information File (CIF) https://doi.org/10.1107/S160053681203574X/xu5610sup1.cif Contains datablocks global, I
	Structure factor file (CIF format) https://doi.org/10.1107/S160053681203574X/xu5610Isup2.hkl Contains datablock I

CCDC reference: 899595

checkCIF report

Key indicators

Single-crystal X-ray study
T = 295 K
Mean (C-C) = 0.005 Å
R factor = 0.040
wR factor = 0.110
Data-to-parameter ratio = 18.1

checkCIF/PLATON results

No syntax errors found



Alert level C
PLAT250_ALERT_2_C Large U3/U1 Ratio for Average U(i,j) Tensor ....        2.1
PLAT905_ALERT_3_C Negative K value in the Analysis of Variance ...     -1.125
PLAT910_ALERT_3_C Missing # of FCF Reflections Below Th(Min) .....          1
PLAT911_ALERT_3_C Missing # FCF Refl Between THmin & STh/L=  0.600          6
PLAT975_ALERT_2_C Positive Residual Density at 0.64A from O2     .       0.61 eA-3

Alert level G
PLAT005_ALERT_5_G No _iucr_refine_instructions_details in CIF ....          ?
PLAT007_ALERT_5_G Note: Number of Unrefined D-H Atoms ............          6
PLAT128_ALERT_4_G Alternate Setting of Space-group P21/c   .......      P21/n
PLAT912_ALERT_4_G Missing # of FCF Reflections Above STh/L=  0.600         37

   0 ALERT level A = Most likely a serious problem - resolve or explain
   0 ALERT level B = A potentially serious problem, consider carefully
   5 ALERT level C = Check. Ensure it is not caused by an omission or oversight
   4 ALERT level G = General information/check it is not something unexpected

   0 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
   3 ALERT type 3 Indicator that the structure quality may be low
   2 ALERT type 4 Improvement, methodology, query or suggestion
   2 ALERT type 5 Informative message, check

Comment top

Salicylaldehyde thiosemicarbazone and its subsituted derivatives are Schiff bases that are capable of N,N',O-chelation to transition metal ions, a feature that has been documented in a plethora of metal derivatives. Several copper derivatives have been reported (Wang et al., 2008; Patole et al., 2001). The Cu^II atom in CuCl(C₉H₁₀N₃O₃) (Scheme I) is N,N',O-chelated by the deprotonated Schiff base, and it exists in a square planar environment in the two independent molecules (Fig. 1). Adjacent molecules are linked by N–H···O and N–H···Cl hydrogen bonds to form a two-dimensional network (Table 1).

Related literature top

For similar copper(II) complexes, see: Wang et al. (2008); Patole et al. (2001).

Experimental top

The Schiff base was prepared by heating 2-hydroxy-4-methoxybenzaldehyde (0.152 g,1 mmol) and semicarbazide hydrochloride (0.111 g,1 mmol) for 3 h. Copper(II) dichloride dihydrate (0.170 g, 1 mmol) was added to the solution and reflux was continued for another 2 h. Dark green colored crystals were isolated from the cool solution.

Computing details top

Data collection: APEX2 (Bruker, 2010); cell refinement: SAINT (Bruker, 2010); data reduction: SAINT (Bruker, 2010); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: X-SEED (Barbour, 2001); software used to prepare material for publication: publCIF (Westrip, 2010).

Figures top

Fig. 1. Thermal ellipsoid plot (Barbour, 2001) of CuCl(C₉H₁₀N₃O₃) at the 70% probability level; hydrogen atoms are drawn as spheres of arbitrary radius.

{2-[(2-Carbamoylhydrazin-1-ylidene)methyl-κ²N¹,O]- 5-methoxyphenolato-κO¹}chloridocopper(II) top

Crystal data top

[Cu(C₉H₁₀N₃O₃)Cl]	F(000) = 1240
M_r = 307.19	D_x = 1.821 Mg m⁻³
Monoclinic, P2₁/n	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2yn	Cell parameters from 5495 reflections
a = 11.8413 (6) Å	θ = 2.3–27.0°
b = 14.2791 (7) Å	µ = 2.19 mm⁻¹
c = 13.5751 (6) Å	T = 295 K
β = 102.501 (2)°	Prism, dark green
V = 2240.90 (19) Å³	0.30 × 0.25 × 0.20 mm
Z = 8

Data collection top

Bruker Kappa APEXII diffractometer	5562 independent reflections
Radiation source: fine-focus sealed tube	3809 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.047
ω scans	θ_max = 28.4°, θ_min = 2.1°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −15→15
T_min = 0.560, T_max = 0.669	k = −17→19
20852 measured reflections	l = −11→18

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)] = 0.040	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.110	H-atom parameters constrained
S = 1.02	w = 1/[σ²(F_o²) + (0.0443P)² + 2.0625P] where P = (F_o² + 2F_c²)/3
5562 reflections	(Δ/σ)_max = 0.001
307 parameters	Δρ_max = 0.57 e Å⁻³
0 restraints	Δρ_min = −0.37 e Å⁻³

Crystal data top

[Cu(C₉H₁₀N₃O₃)Cl]	V = 2240.90 (19) Å³
M_r = 307.19	Z = 8
Monoclinic, P2₁/n	Mo Kα radiation
a = 11.8413 (6) Å	µ = 2.19 mm⁻¹
b = 14.2791 (7) Å	T = 295 K
c = 13.5751 (6) Å	0.30 × 0.25 × 0.20 mm
β = 102.501 (2)°

Data collection top

Bruker Kappa APEXII diffractometer	5562 independent reflections
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	3809 reflections with I > 2σ(I)
T_min = 0.560, T_max = 0.669	R_int = 0.047
20852 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.040	0 restraints
wR(F²) = 0.110	H-atom parameters constrained
S = 1.02	Δρ_max = 0.57 e Å⁻³
5562 reflections	Δρ_min = −0.37 e Å⁻³
307 parameters

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å²) top

	x	y	z	U_iso*/U_eq
Cu1	0.29935 (3)	0.85386 (3)	0.32124 (3)	0.03357 (12)
Cu2	0.79752 (3)	0.56618 (3)	0.33325 (3)	0.03219 (12)
Cl1	0.11883 (7)	0.88631 (6)	0.33195 (7)	0.0418 (2)
Cl2	0.61629 (7)	0.53124 (6)	0.33804 (8)	0.0509 (3)
O1	0.6111 (2)	1.23052 (19)	0.4410 (2)	0.0569 (7)
O2	0.35126 (19)	0.97847 (15)	0.33806 (18)	0.0365 (5)
O3	0.25915 (19)	0.72346 (16)	0.2833 (2)	0.0446 (6)
O4	1.1173 (2)	0.19137 (16)	0.4510 (2)	0.0488 (6)
O5	0.85178 (17)	0.44138 (14)	0.35581 (17)	0.0334 (5)
O6	0.75675 (19)	0.69642 (15)	0.29078 (18)	0.0380 (5)
N1	0.4534 (2)	0.80675 (18)	0.3315 (2)	0.0324 (6)
N2	0.4528 (2)	0.71236 (19)	0.3109 (2)	0.0396 (7)
H1	0.5168	0.6802	0.3132	0.048*
N3	0.3391 (3)	0.58301 (19)	0.2679 (3)	0.0495 (8)
H2	0.2709	0.5559	0.2522	0.059*
H3	0.4023	0.5497	0.2710	0.059*
N4	0.9510 (2)	0.61509 (17)	0.34674 (18)	0.0276 (5)
N5	0.9498 (2)	0.70935 (17)	0.3251 (2)	0.0330 (6)
H4	1.0136	0.7425	0.3314	0.040*
N6	0.8360 (2)	0.83611 (18)	0.2675 (2)	0.0400 (7)
H5	0.7678	0.8625	0.2471	0.048*
H6	0.8993	0.8692	0.2706	0.048*
C1	0.5869 (3)	1.1399 (2)	0.4154 (3)	0.0409 (8)
C2	0.4767 (3)	1.1034 (2)	0.3879 (2)	0.0357 (7)
H2A	0.4132	1.1426	0.3843	0.043*
C3	0.4589 (3)	1.0082 (2)	0.3654 (2)	0.0310 (7)
C4	0.5574 (3)	0.9494 (2)	0.3722 (2)	0.0325 (7)
C5	0.6682 (3)	0.9899 (3)	0.3998 (3)	0.0414 (8)
H5A	0.7329	0.9519	0.4040	0.050*
C6	0.6834 (3)	1.0825 (3)	0.4205 (3)	0.0459 (9)
H6A	0.7576	1.1075	0.4380	0.055*
C7	0.5192 (4)	1.2946 (3)	0.4323 (3)	0.0632 (12)
H7A	0.5493	1.3555	0.4535	0.095*
H7B	0.4679	1.2746	0.4741	0.095*
H7C	0.4776	1.2974	0.3633	0.095*
C8	0.5499 (3)	0.8510 (2)	0.3526 (2)	0.0340 (7)
H8	0.6179	0.8176	0.3552	0.041*
C9	0.3466 (3)	0.6727 (2)	0.2867 (3)	0.0366 (7)
C10	1.0904 (3)	0.2828 (2)	0.4312 (2)	0.0349 (7)
C11	0.9796 (3)	0.3175 (2)	0.4037 (2)	0.0326 (7)
H11	0.9171	0.2770	0.3988	0.039*
C12	0.9595 (2)	0.4135 (2)	0.3829 (2)	0.0268 (6)
C13	1.0564 (3)	0.4741 (2)	0.3919 (2)	0.0291 (6)
C14	1.1674 (3)	0.4347 (2)	0.4214 (3)	0.0376 (8)
H14	1.2313	0.4740	0.4279	0.045*
C15	1.1859 (3)	0.3423 (2)	0.4406 (3)	0.0412 (8)
H15	1.2607	0.3188	0.4598	0.049*
C16	1.0267 (3)	0.1256 (2)	0.4431 (3)	0.0516 (10)
H16A	1.0587	0.0643	0.4593	0.077*
H16B	0.9811	0.1257	0.3754	0.077*
H16C	0.9788	0.1421	0.4891	0.077*
C17	1.0479 (3)	0.5715 (2)	0.3717 (2)	0.0311 (7)
H17	1.1158	0.6056	0.3767	0.037*
C18	0.8432 (3)	0.7473 (2)	0.2934 (2)	0.0322 (7)

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Cu1	0.0244 (2)	0.0258 (2)	0.0503 (3)	−0.00060 (15)	0.00748 (16)	−0.00107 (17)
Cu2	0.0229 (2)	0.0211 (2)	0.0503 (3)	0.00078 (14)	0.00288 (16)	0.00072 (16)
Cl1	0.0258 (4)	0.0332 (4)	0.0670 (6)	−0.0013 (3)	0.0116 (4)	−0.0007 (4)
Cl2	0.0247 (4)	0.0293 (4)	0.0961 (8)	−0.0006 (3)	0.0073 (4)	−0.0012 (4)
O1	0.0594 (18)	0.0400 (16)	0.0694 (19)	−0.0185 (13)	0.0099 (14)	−0.0094 (13)
O2	0.0285 (12)	0.0257 (12)	0.0548 (15)	−0.0006 (9)	0.0081 (10)	−0.0012 (10)
O3	0.0277 (12)	0.0296 (13)	0.0749 (18)	−0.0020 (10)	0.0079 (11)	−0.0087 (12)
O4	0.0478 (16)	0.0282 (13)	0.0696 (18)	0.0131 (11)	0.0107 (12)	0.0097 (12)
O5	0.0226 (11)	0.0229 (11)	0.0524 (14)	0.0008 (8)	0.0031 (9)	−0.0013 (9)
O6	0.0301 (12)	0.0244 (12)	0.0585 (15)	0.0019 (9)	0.0074 (10)	0.0048 (10)
N1	0.0311 (14)	0.0290 (14)	0.0372 (15)	0.0004 (11)	0.0075 (11)	−0.0017 (11)
N2	0.0329 (15)	0.0260 (14)	0.0595 (19)	0.0039 (11)	0.0092 (13)	−0.0029 (13)
N3	0.0340 (17)	0.0280 (16)	0.085 (2)	0.0026 (12)	0.0091 (15)	−0.0099 (15)
N4	0.0266 (13)	0.0216 (13)	0.0342 (14)	−0.0005 (10)	0.0056 (10)	0.0025 (10)
N5	0.0277 (14)	0.0197 (13)	0.0507 (17)	0.0001 (10)	0.0068 (11)	0.0050 (11)
N6	0.0308 (15)	0.0249 (14)	0.0628 (19)	0.0023 (11)	0.0072 (13)	0.0098 (13)
C1	0.048 (2)	0.037 (2)	0.0372 (19)	−0.0124 (16)	0.0101 (15)	−0.0028 (15)
C2	0.0386 (19)	0.0313 (18)	0.0373 (18)	−0.0030 (14)	0.0085 (14)	0.0019 (14)
C3	0.0302 (17)	0.0312 (17)	0.0322 (17)	−0.0043 (13)	0.0081 (12)	0.0009 (13)
C4	0.0277 (16)	0.0359 (18)	0.0348 (17)	−0.0039 (13)	0.0086 (12)	0.0009 (13)
C5	0.0289 (18)	0.047 (2)	0.048 (2)	−0.0052 (15)	0.0064 (14)	−0.0006 (16)
C6	0.0335 (19)	0.052 (2)	0.050 (2)	−0.0151 (16)	0.0043 (15)	−0.0052 (17)
C7	0.086 (3)	0.041 (2)	0.060 (3)	−0.006 (2)	0.011 (2)	−0.0008 (19)
C8	0.0242 (16)	0.0371 (19)	0.0413 (19)	0.0014 (13)	0.0081 (13)	0.0018 (14)
C9	0.0308 (18)	0.0292 (17)	0.049 (2)	−0.0027 (13)	0.0069 (14)	−0.0014 (15)
C10	0.0394 (19)	0.0269 (17)	0.0378 (19)	0.0088 (13)	0.0071 (13)	0.0021 (13)
C11	0.0319 (17)	0.0275 (17)	0.0374 (18)	0.0013 (12)	0.0058 (13)	0.0003 (13)
C12	0.0248 (15)	0.0261 (16)	0.0287 (16)	0.0025 (11)	0.0042 (11)	−0.0012 (12)
C13	0.0258 (16)	0.0264 (16)	0.0346 (17)	0.0034 (12)	0.0052 (12)	−0.0008 (12)
C14	0.0257 (17)	0.0343 (19)	0.051 (2)	0.0021 (13)	0.0044 (14)	0.0026 (15)
C15	0.0286 (18)	0.038 (2)	0.056 (2)	0.0098 (14)	0.0055 (15)	0.0082 (16)
C16	0.060 (3)	0.0251 (18)	0.070 (3)	0.0024 (17)	0.015 (2)	0.0074 (17)
C17	0.0242 (16)	0.0297 (17)	0.0392 (18)	−0.0005 (12)	0.0063 (12)	−0.0002 (13)
C18	0.0305 (17)	0.0270 (16)	0.0397 (18)	0.0024 (13)	0.0087 (13)	−0.0001 (13)

Geometric parameters (Å, º) top

Cu1—O2	1.880 (2)	N6—H6	0.8800
Cu1—N1	1.920 (3)	C1—C2	1.380 (5)
Cu1—O3	1.963 (2)	C1—C6	1.396 (5)
Cu1—Cl1	2.2225 (9)	C2—C3	1.398 (4)
Cu2—O5	1.897 (2)	C2—H2A	0.9300
Cu2—N4	1.918 (2)	C3—C4	1.424 (4)
Cu2—O6	1.976 (2)	C4—C5	1.408 (4)
Cu2—Cl2	2.2179 (9)	C4—C8	1.429 (4)
O1—C1	1.354 (4)	C5—C6	1.356 (5)
O1—C7	1.408 (5)	C5—H5A	0.9300
O2—C3	1.319 (4)	C6—H6A	0.9300
O3—C9	1.257 (4)	C7—H7A	0.9600
O4—C10	1.357 (4)	C7—H7B	0.9600
O4—C16	1.412 (4)	C7—H7C	0.9600
O5—C12	1.311 (3)	C8—H8	0.9300
O6—C18	1.250 (4)	C10—C11	1.376 (4)
N1—C8	1.283 (4)	C10—C15	1.398 (5)
N1—N2	1.376 (4)	C11—C12	1.409 (4)
N2—C9	1.353 (4)	C11—H11	0.9300
N2—H1	0.8800	C12—C13	1.422 (4)
N3—C9	1.305 (4)	C13—C14	1.406 (4)
N3—H2	0.8800	C13—C17	1.417 (4)
N3—H3	0.8800	C14—C15	1.354 (4)
N4—C17	1.284 (4)	C14—H14	0.9300
N4—N5	1.377 (3)	C15—H15	0.9300
N5—C18	1.355 (4)	C16—H16A	0.9600
N5—H4	0.8800	C16—H16B	0.9600
N6—C18	1.314 (4)	C16—H16C	0.9600
N6—H5	0.8800	C17—H17	0.9300

O2—Cu1—N1	92.42 (10)	C6—C5—C4	122.0 (3)
O2—Cu1—O3	169.71 (10)	C6—C5—H5A	119.0
N1—Cu1—O3	81.91 (10)	C4—C5—H5A	119.0
O2—Cu1—Cl1	95.08 (7)	C5—C6—C1	119.5 (3)
N1—Cu1—Cl1	168.53 (8)	C5—C6—H6A	120.3
O3—Cu1—Cl1	91.89 (7)	C1—C6—H6A	120.3
O5—Cu2—N4	92.63 (10)	O1—C7—H7A	109.5
O5—Cu2—O6	169.86 (10)	O1—C7—H7B	109.5
N4—Cu2—O6	81.48 (10)	H7A—C7—H7B	109.5
O5—Cu2—Cl2	94.59 (7)	O1—C7—H7C	109.5
N4—Cu2—Cl2	169.05 (8)	H7A—C7—H7C	109.5
O6—Cu2—Cl2	92.49 (7)	H7B—C7—H7C	109.5
C1—O1—C7	118.8 (3)	N1—C8—C4	122.8 (3)
C3—O2—Cu1	127.6 (2)	N1—C8—H8	118.6
C9—O3—Cu1	112.7 (2)	C4—C8—H8	118.6
C10—O4—C16	118.8 (3)	O3—C9—N3	122.5 (3)
C12—O5—Cu2	127.32 (19)	O3—C9—N2	118.8 (3)
C18—O6—Cu2	113.1 (2)	N3—C9—N2	118.6 (3)
C8—N1—N2	119.5 (3)	O4—C10—C11	124.7 (3)
C8—N1—Cu1	129.0 (2)	O4—C10—C15	114.6 (3)
N2—N1—Cu1	111.46 (19)	C11—C10—C15	120.7 (3)
C9—N2—N1	115.0 (3)	C10—C11—C12	120.9 (3)
C9—N2—H1	122.5	C10—C11—H11	119.5
N1—N2—H1	122.5	C12—C11—H11	119.5
C9—N3—H2	120.0	O5—C12—C11	117.6 (3)
C9—N3—H3	120.0	O5—C12—C13	123.9 (3)
H2—N3—H3	120.0	C11—C12—C13	118.5 (3)
C17—N4—N5	119.8 (3)	C14—C13—C17	118.1 (3)
C17—N4—Cu2	128.5 (2)	C14—C13—C12	117.9 (3)
N5—N4—Cu2	111.69 (18)	C17—C13—C12	124.0 (3)
C18—N5—N4	115.1 (2)	C15—C14—C13	123.2 (3)
C18—N5—H4	122.4	C15—C14—H14	118.4
N4—N5—H4	122.4	C13—C14—H14	118.4
C18—N6—H5	120.0	C14—C15—C10	118.7 (3)
C18—N6—H6	120.0	C14—C15—H15	120.6
H5—N6—H6	120.0	C10—C15—H15	120.6
O1—C1—C2	124.5 (3)	O4—C16—H16A	109.5
O1—C1—C6	115.0 (3)	O4—C16—H16B	109.5
C2—C1—C6	120.5 (3)	H16A—C16—H16B	109.5
C1—C2—C3	121.0 (3)	O4—C16—H16C	109.5
C1—C2—H2A	119.5	H16A—C16—H16C	109.5
C3—C2—H2A	119.5	H16B—C16—H16C	109.5
O2—C3—C2	117.7 (3)	N4—C17—C13	123.3 (3)
O2—C3—C4	123.8 (3)	N4—C17—H17	118.3
C2—C3—C4	118.5 (3)	C13—C17—H17	118.3
C5—C4—C3	118.5 (3)	O6—C18—N6	123.2 (3)
C5—C4—C8	118.0 (3)	O6—C18—N5	118.5 (3)
C3—C4—C8	123.4 (3)	N6—C18—N5	118.2 (3)

N1—Cu1—O2—C3	−10.5 (3)	C2—C3—C4—C8	179.0 (3)
O3—Cu1—O2—C3	−66.8 (7)	C3—C4—C5—C6	0.5 (5)
Cl1—Cu1—O2—C3	160.8 (2)	C8—C4—C5—C6	−179.5 (3)
O2—Cu1—O3—C9	59.4 (7)	C4—C5—C6—C1	0.5 (5)
N1—Cu1—O3—C9	2.3 (2)	O1—C1—C6—C5	177.6 (3)
Cl1—Cu1—O3—C9	−168.0 (2)	C2—C1—C6—C5	−1.0 (5)
N4—Cu2—O5—C12	7.3 (3)	N2—N1—C8—C4	178.3 (3)
O6—Cu2—O5—C12	61.4 (6)	Cu1—N1—C8—C4	−0.6 (5)
Cl2—Cu2—O5—C12	−164.5 (2)	C5—C4—C8—N1	176.7 (3)
O5—Cu2—O6—C18	−55.8 (6)	C3—C4—C8—N1	−3.2 (5)
N4—Cu2—O6—C18	−0.9 (2)	Cu1—O3—C9—N3	177.4 (3)
Cl2—Cu2—O6—C18	169.9 (2)	Cu1—O3—C9—N2	−2.5 (4)
O2—Cu1—N1—C8	5.9 (3)	N1—N2—C9—O3	1.1 (5)
O3—Cu1—N1—C8	177.3 (3)	N1—N2—C9—N3	−178.8 (3)
Cl1—Cu1—N1—C8	−124.9 (4)	C16—O4—C10—C11	0.3 (5)
O2—Cu1—N1—N2	−173.0 (2)	C16—O4—C10—C15	−179.7 (3)
O3—Cu1—N1—N2	−1.7 (2)	O4—C10—C11—C12	−179.0 (3)
Cl1—Cu1—N1—N2	56.1 (5)	C15—C10—C11—C12	1.0 (5)
C8—N1—N2—C9	−178.2 (3)	Cu2—O5—C12—C11	174.7 (2)
Cu1—N1—N2—C9	0.9 (3)	Cu2—O5—C12—C13	−5.6 (4)
O5—Cu2—N4—C17	−5.5 (3)	C10—C11—C12—O5	179.1 (3)
O6—Cu2—N4—C17	−177.2 (3)	C10—C11—C12—C13	−0.7 (4)
Cl2—Cu2—N4—C17	125.8 (4)	O5—C12—C13—C14	−179.8 (3)
O5—Cu2—N4—N5	174.17 (19)	C11—C12—C13—C14	−0.1 (4)
O6—Cu2—N4—N5	2.46 (19)	O5—C12—C13—C17	−0.7 (5)
Cl2—Cu2—N4—N5	−54.6 (5)	C11—C12—C13—C17	179.0 (3)
C17—N4—N5—C18	175.9 (3)	C17—C13—C14—C15	−178.6 (3)
Cu2—N4—N5—C18	−3.7 (3)	C12—C13—C14—C15	0.5 (5)
C7—O1—C1—C2	−5.1 (5)	C13—C14—C15—C10	−0.2 (5)
C7—O1—C1—C6	176.3 (3)	O4—C10—C15—C14	179.4 (3)
O1—C1—C2—C3	−178.0 (3)	C11—C10—C15—C14	−0.6 (5)
C6—C1—C2—C3	0.5 (5)	N5—N4—C17—C13	−177.9 (3)
Cu1—O2—C3—C2	−170.5 (2)	Cu2—N4—C17—C13	1.7 (5)
Cu1—O2—C3—C4	10.1 (4)	C14—C13—C17—N4	−178.2 (3)
C1—C2—C3—O2	−178.9 (3)	C12—C13—C17—N4	2.7 (5)
C1—C2—C3—C4	0.5 (5)	Cu2—O6—C18—N6	179.5 (3)
O2—C3—C4—C5	178.4 (3)	Cu2—O6—C18—N5	−1.0 (4)
C2—C3—C4—C5	−1.0 (4)	N4—N5—C18—O6	3.2 (4)
O2—C3—C4—C8	−1.6 (5)	N4—N5—C18—N6	−177.2 (3)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N2—H1···Cl2	0.88	2.42	3.203 (3)	149
N3—H2···O2ⁱ	0.88	2.01	2.824 (4)	153
N3—H3···Cl2	0.88	2.51	3.297 (3)	149
N5—H4···Cl1ⁱⁱ	0.88	2.40	3.212 (3)	154
N6—H5···O5ⁱⁱⁱ	0.88	2.09	2.897 (3)	152
N6—H6···Cl1ⁱⁱ	0.88	2.56	3.351 (3)	149

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

Experimental details

Crystal data
Chemical formula	[Cu(C₉H₁₀N₃O₃)Cl]
M_r	307.19
Crystal system, space group	Monoclinic, P2₁/n
Temperature (K)	295
a, b, c (Å)	11.8413 (6), 14.2791 (7), 13.5751 (6)
β (°)	102.501 (2)
V (Å³)	2240.90 (19)
Z	8
Radiation type	Mo Kα
µ (mm⁻¹)	2.19
Crystal size (mm)	0.30 × 0.25 × 0.20

Data collection
Diffractometer	Bruker Kappa APEXII diffractometer
Absorption correction	Multi-scan (SADABS; Sheldrick, 1996)
T_min, T_max	0.560, 0.669
No. of measured, independent and observed [I > 2σ(I)] reflections	20852, 5562, 3809
R_int	0.047
(sin θ/λ)_max (Å⁻¹)	0.669

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.040, 0.110, 1.02
No. of reflections	5562
No. of parameters	307
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.57, −0.37

Computer programs: APEX2 (Bruker, 2010), SAINT (Bruker, 2010), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), X-SEED (Barbour, 2001), publCIF (Westrip, 2010).