Bis(2,2′-bipyridine-κ²N,N′)(hippurato-κO)copper(II) perchlorate dihydrate

In the title complex, [Cu(C₉H₈NO₃)(C₁₀H₈N₂)₂]ClO₄·2H₂O, the CuN₄O₂ chromophore exhibits a square-pyramidal geometry that is distorted towards octa­hedral owing to an intra­molecular Cu...O contact from the double-bond carboxyl­ate O atom. The cations, anions and solvent water mol­ecules are linked by hydrogen bonds into a linear chain running along the b axis.

Key indicators

• Single-crystal X-ray study
• T = 298 K
• Mean [sigma](C-C) = 0.004 Å
• R factor = 0.041
• wR factor = 0.118
• Data-to-parameter ratio = 18.6

checkCIF/PLATON results

No syntax errors found



Alert level C
PLAT232_ALERT_2_C Hirshfeld Test Diff (M-X)  Cu1    -   N1      ..       5.07 su
PLAT241_ALERT_2_C Check High      Ueq as Compared to Neighbors for         O2
PLAT244_ALERT_4_C Low   'Solvent' Ueq as Compared to Neighbors for        Cl1
PLAT245_ALERT_2_C U(iso) H1A     Smaller than U(eq) O1W     by ...       0.03 AngSq
PLAT245_ALERT_2_C U(iso) H1B     Smaller than U(eq) O1W     by ...       0.03 AngSq

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

   0 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
   4 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
   1 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, 2004); cell refinement: SAINT (Bruker, 2004); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: SHELXTL (Bruker, 1997); software used to prepare material for publication: SHELXTL.

Bis(2,2'-bipyridine-κ²N,N')(hippurato-κO)copper(II) perchlorate dihydrate

Crystal data

[Cu(C9H8NO3)(C10H8N2)2]ClO4·2H2O	F(000) = 1420
Mr = 689.55	Dx = 1.509 Mg m^−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 2500 reflections
a = 15.3323 (15) Å	θ = 0.9–27.5°
b = 10.3718 (10) Å	µ = 0.87 mm^−1
c = 19.5278 (19) Å	T = 298 K
β = 102.253 (1)°	Prism, blue
V = 3034.6 (5) Å^3	0.41 × 0.31 × 0.26 mm
Z = 4

Data collection

Bruker SMART APEX-II CCD diffractometer	7589 independent reflections
Radiation source: fine-focus sealed tube	5108 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.036
Detector resolution: 8.35 pixels mm^-1	θmax = 28.5°, θmin = 2.4°
ω scans	h = −20→20
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	k = −13→13
Tmin = 0.740, Tmax = 0.801	l = −25→25
27041 measured reflections

Refinement

Refinement on F^2	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F^2 > 2σ(F^2)] = 0.041	H-atom parameters constrained
wR(F^2) = 0.118	w = 1/[σ^2(Fo^2) + (0.0557P)^2 + 0.6157P] where P = (Fo^2 + 2Fc^2)/3
S = 1.02	(Δ/σ)max = 0.001
7589 reflections	Δρmax = 0.38 e Å^−3
407 parameters	Δρmin = −0.42 e Å^−3
0 restraints	Extinction correction: SHELXL97, Fc^*=kFc[1+0.001xFc^2λ^3/sin(2θ)]^-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.0029 (4)

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
Cu1	0.248199 (18)	1.02074 (3)	0.490802 (15)	0.04546 (11)
Cl1	0.64140 (5)	0.50181 (7)	0.35647 (4)	0.06217 (19)
O4	0.7265 (2)	0.5480 (4)	0.3558 (2)	0.1539 (14)
O5	0.5772 (2)	0.6015 (3)	0.34309 (16)	0.1228 (10)
O6	0.6386 (2)	0.4478 (3)	0.42273 (14)	0.1258 (10)
O7	0.61945 (14)	0.4038 (2)	0.30467 (12)	0.0844 (6)
N1	0.17975 (12)	0.86873 (19)	0.51187 (10)	0.0486 (5)
N2	0.16431 (12)	1.1110 (2)	0.54509 (10)	0.0485 (5)
C1	0.19282 (18)	0.7478 (3)	0.49345 (15)	0.0618 (7)
H1	0.2345	0.7321	0.4661	0.074*
C2	0.1471 (2)	0.6450 (3)	0.51337 (18)	0.0777 (9)
H2	0.1579	0.5613	0.5002	0.093*
C3	0.0848 (2)	0.6693 (3)	0.55324 (19)	0.0827 (10)
H3	0.0529	0.6017	0.5674	0.099*
C4	0.07011 (19)	0.7930 (3)	0.57183 (15)	0.0699 (8)
H4	0.0282	0.8100	0.5988	0.084*
C5	0.11782 (15)	0.8931 (3)	0.55035 (12)	0.0499 (6)
C6	0.10591 (15)	1.0298 (2)	0.56557 (12)	0.0480 (5)
C7	0.03916 (16)	1.0755 (3)	0.59773 (13)	0.0623 (7)
H7	−0.0014	1.0187	0.6107	0.075*
C8	0.03383 (19)	1.2050 (3)	0.61004 (14)	0.0730 (9)
H8	−0.0108	1.2370	0.6310	0.088*
C9	0.0949 (2)	1.2874 (3)	0.59108 (15)	0.0730 (8)
H9	0.0931	1.3754	0.5998	0.088*
C10	0.15889 (18)	1.2366 (3)	0.55883 (14)	0.0599 (7)
H10	0.2002	1.2923	0.5460	0.072*
N3	0.31849 (13)	1.17635 (19)	0.47625 (10)	0.0505 (5)
N4	0.37486 (12)	0.97782 (19)	0.55816 (10)	0.0471 (4)
C11	0.2856 (2)	1.2715 (3)	0.43189 (13)	0.0621 (7)
H11	0.2260	1.2683	0.4088	0.074*
C12	0.3370 (2)	1.3735 (3)	0.41943 (15)	0.0719 (8)
H12	0.3124	1.4388	0.3887	0.086*
C13	0.4246 (2)	1.3778 (3)	0.45261 (16)	0.0757 (9)
H13	0.4609	1.4450	0.4438	0.091*
C14	0.4589 (2)	1.2822 (3)	0.49915 (15)	0.0665 (8)
H14	0.5183	1.2854	0.5228	0.080*
C15	0.40494 (16)	1.1808 (2)	0.51105 (12)	0.0504 (6)
C16	0.43575 (15)	1.0717 (3)	0.55820 (12)	0.0497 (6)
C17	0.52117 (17)	1.0617 (3)	0.59986 (15)	0.0656 (8)
H17	0.5625	1.1272	0.5995	0.079*
C18	0.54420 (19)	0.9555 (3)	0.64130 (16)	0.0708 (8)
H18	0.6012	0.9481	0.6692	0.085*
C19	0.48237 (18)	0.8601 (3)	0.64133 (14)	0.0647 (7)
H19	0.4966	0.7869	0.6690	0.078*
C20	0.39807 (16)	0.8752 (3)	0.59921 (13)	0.0547 (6)
H20	0.3558	0.8110	0.5996	0.066*
O1	0.25799 (11)	0.94056 (17)	0.39600 (9)	0.0532 (4)
O2	0.13788 (12)	1.06382 (18)	0.36513 (10)	0.0629 (5)
C21	0.19332 (16)	0.9838 (2)	0.35148 (13)	0.0492 (6)
C22	0.18132 (19)	0.9418 (3)	0.27542 (13)	0.0572 (6)
H23	0.1181	0.9300	0.2563	0.069*
H22	0.2019	1.0108	0.2493	0.069*
N5	0.22737 (14)	0.8246 (2)	0.26407 (10)	0.0548 (5)
H5	0.2750	0.8297	0.2475	0.066*
C23	0.19808 (16)	0.7093 (2)	0.27852 (12)	0.0495 (6)
C24	0.24936 (15)	0.5939 (2)	0.26448 (12)	0.0494 (6)
C25	0.20364 (18)	0.4793 (3)	0.24717 (14)	0.0591 (7)
H25	0.1424	0.4769	0.2448	0.071*
C26	0.2466 (2)	0.3688 (3)	0.23340 (15)	0.0736 (8)
H26	0.2146	0.2929	0.2217	0.088*
C27	0.3376 (2)	0.3712 (3)	0.23709 (15)	0.0755 (9)
H27	0.3670	0.2975	0.2271	0.091*
C28	0.3841 (2)	0.4830 (3)	0.25558 (17)	0.0746 (9)
H28	0.4455	0.4839	0.2592	0.090*
C29	0.34098 (17)	0.5954 (3)	0.26905 (14)	0.0618 (7)
H29	0.3733	0.6710	0.2810	0.074*
O1W	0.0588 (2)	0.4796 (2)	0.36910 (17)	0.1294 (12)
O2W	0.04166 (15)	0.2561 (2)	0.28714 (12)	0.0857 (6)
O3	0.12940 (11)	0.69794 (18)	0.30220 (10)	0.0646 (5)
H2B	0.0723	0.1920	0.3054	0.097*
H1B	0.1048	0.5155	0.3593	0.097*
H1A	0.0464	0.4206	0.3383	0.097*
H2A	−0.0066	0.2342	0.2592	0.097*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
Cu1	0.04317 (17)	0.04653 (18)	0.05091 (18)	−0.00764 (12)	0.01948 (12)	0.00165 (12)
Cl1	0.0609 (4)	0.0630 (4)	0.0644 (4)	−0.0055 (3)	0.0172 (3)	−0.0092 (3)
O4	0.109 (2)	0.174 (3)	0.194 (3)	−0.076 (2)	0.066 (2)	−0.073 (3)
O5	0.140 (2)	0.0822 (18)	0.143 (2)	0.0371 (17)	0.0243 (19)	−0.0086 (17)
O6	0.169 (3)	0.139 (3)	0.0811 (18)	0.029 (2)	0.0509 (18)	0.0059 (16)
O7	0.0794 (14)	0.0846 (15)	0.0930 (15)	−0.0053 (12)	0.0268 (12)	−0.0300 (12)
N1	0.0439 (10)	0.0502 (12)	0.0534 (11)	−0.0045 (9)	0.0142 (9)	0.0059 (9)
N2	0.0446 (10)	0.0584 (13)	0.0451 (11)	−0.0030 (9)	0.0150 (8)	−0.0001 (9)
C1	0.0612 (16)	0.0525 (16)	0.0735 (18)	−0.0050 (13)	0.0180 (13)	0.0038 (13)
C2	0.081 (2)	0.0504 (17)	0.099 (2)	−0.0111 (15)	0.0128 (18)	0.0107 (15)
C3	0.081 (2)	0.073 (2)	0.097 (2)	−0.0245 (17)	0.0242 (18)	0.0268 (18)
C4	0.0635 (17)	0.085 (2)	0.0665 (18)	−0.0173 (15)	0.0255 (14)	0.0159 (15)
C5	0.0401 (12)	0.0664 (16)	0.0435 (12)	−0.0095 (11)	0.0090 (10)	0.0096 (11)
C6	0.0386 (12)	0.0695 (16)	0.0365 (11)	−0.0041 (11)	0.0096 (9)	0.0033 (11)
C7	0.0435 (14)	0.098 (2)	0.0481 (14)	0.0011 (14)	0.0160 (11)	0.0034 (14)
C8	0.0569 (17)	0.110 (3)	0.0547 (16)	0.0223 (17)	0.0171 (13)	−0.0084 (16)
C9	0.0743 (19)	0.076 (2)	0.0709 (19)	0.0177 (16)	0.0197 (15)	−0.0119 (15)
C10	0.0644 (16)	0.0563 (16)	0.0625 (16)	0.0028 (13)	0.0214 (13)	−0.0068 (12)
N3	0.0573 (12)	0.0521 (12)	0.0466 (11)	−0.0120 (10)	0.0211 (9)	−0.0009 (9)
N4	0.0414 (10)	0.0547 (12)	0.0478 (11)	−0.0050 (9)	0.0153 (8)	−0.0057 (9)
C11	0.0777 (18)	0.0573 (16)	0.0533 (15)	−0.0152 (14)	0.0187 (13)	0.0044 (12)
C12	0.111 (3)	0.0574 (17)	0.0528 (16)	−0.0241 (16)	0.0304 (16)	−0.0028 (13)
C13	0.110 (3)	0.0613 (18)	0.0663 (18)	−0.0436 (18)	0.0416 (18)	−0.0159 (15)
C14	0.0710 (18)	0.0691 (18)	0.0665 (17)	−0.0318 (15)	0.0307 (14)	−0.0219 (15)
C15	0.0544 (14)	0.0572 (15)	0.0469 (13)	−0.0178 (11)	0.0269 (11)	−0.0169 (11)
C16	0.0452 (13)	0.0629 (15)	0.0459 (13)	−0.0103 (11)	0.0205 (10)	−0.0165 (11)
C17	0.0444 (14)	0.089 (2)	0.0663 (17)	−0.0156 (14)	0.0185 (13)	−0.0235 (16)
C18	0.0474 (15)	0.101 (2)	0.0630 (18)	0.0061 (16)	0.0085 (13)	−0.0144 (17)
C19	0.0584 (16)	0.080 (2)	0.0558 (16)	0.0128 (14)	0.0128 (13)	−0.0046 (14)
C20	0.0508 (14)	0.0619 (16)	0.0523 (14)	0.0006 (12)	0.0128 (11)	−0.0022 (12)
O1	0.0489 (9)	0.0627 (11)	0.0515 (10)	−0.0073 (8)	0.0187 (8)	−0.0003 (8)
O2	0.0622 (11)	0.0623 (11)	0.0703 (12)	0.0009 (9)	0.0275 (9)	−0.0068 (9)
C21	0.0508 (14)	0.0480 (13)	0.0546 (14)	−0.0138 (11)	0.0238 (12)	−0.0002 (11)
C22	0.0683 (16)	0.0549 (15)	0.0515 (14)	−0.0021 (13)	0.0196 (12)	0.0016 (11)
N5	0.0608 (13)	0.0576 (13)	0.0530 (12)	−0.0034 (10)	0.0279 (10)	−0.0010 (10)
C23	0.0473 (13)	0.0570 (15)	0.0464 (13)	−0.0026 (11)	0.0147 (10)	−0.0013 (11)
C24	0.0480 (13)	0.0616 (15)	0.0416 (12)	0.0014 (11)	0.0164 (10)	0.0032 (11)
C25	0.0543 (15)	0.0673 (17)	0.0546 (15)	0.0018 (13)	0.0089 (12)	−0.0100 (12)
C26	0.082 (2)	0.070 (2)	0.0647 (18)	0.0095 (16)	0.0065 (15)	−0.0150 (14)
C27	0.090 (2)	0.081 (2)	0.0600 (18)	0.0277 (19)	0.0253 (16)	0.0055 (15)
C28	0.0540 (16)	0.104 (3)	0.074 (2)	0.0227 (17)	0.0317 (15)	0.0273 (18)
C29	0.0478 (14)	0.0777 (19)	0.0639 (16)	0.0008 (13)	0.0211 (12)	0.0165 (14)
O1W	0.190 (3)	0.0897 (18)	0.141 (3)	−0.0559 (19)	0.109 (2)	−0.0371 (16)
O2W	0.0828 (14)	0.0752 (14)	0.0933 (16)	−0.0035 (11)	0.0060 (12)	−0.0020 (12)
O3	0.0532 (10)	0.0629 (12)	0.0864 (13)	0.0007 (8)	0.0345 (10)	0.0046 (10)

Geometric parameters (Å, º)

Cu1—N1	1.9849 (19)	C13—C14	1.372 (4)
Cu1—N2	2.0576 (19)	C13—H13	0.9300
Cu1—N3	1.9943 (19)	C14—C15	1.388 (3)
Cu1—N4	2.148 (2)	C14—H14	0.9300
Cu1—O1	2.0639 (17)	C15—C16	1.472 (4)
Cu1—O2	2.7058 (19)	C16—C17	1.391 (3)
Cl1—O4	1.393 (3)	C17—C18	1.368 (4)
Cl1—O5	1.413 (3)	C17—H17	0.9300
Cl1—O6	1.419 (3)	C18—C19	1.371 (4)
Cl1—O7	1.423 (2)	C18—H18	0.9300
N1—C1	1.332 (3)	C19—C20	1.386 (3)
N1—C5	1.354 (3)	C19—H19	0.9300
N2—C10	1.336 (3)	C20—H20	0.9300
N2—C6	1.350 (3)	O1—C21	1.255 (3)
C1—C2	1.377 (4)	O2—C21	1.256 (3)
C1—H1	0.9300	C21—C22	1.521 (3)
C2—C3	1.377 (5)	C22—N5	1.446 (3)
C2—H2	0.9300	C22—H23	0.9700
C3—C4	1.365 (5)	C22—H22	0.9700
C3—H3	0.9300	N5—C23	1.329 (3)
C4—C5	1.385 (3)	N5—H5	0.8600
C4—H4	0.9300	C23—O3	1.242 (3)
C5—C6	1.468 (4)	C23—C24	1.489 (3)
C6—C7	1.392 (3)	C24—C25	1.385 (4)
C7—C8	1.371 (4)	C24—C29	1.389 (3)
C7—H7	0.9300	C25—C26	1.377 (4)
C8—C9	1.375 (4)	C25—H25	0.9300
C8—H8	0.9300	C26—C27	1.382 (4)
C9—C10	1.378 (4)	C26—H26	0.9300
C9—H9	0.9300	C27—C28	1.369 (4)
C10—H10	0.9300	C27—H27	0.9300
N3—C11	1.339 (3)	C28—C29	1.392 (4)
N3—C15	1.356 (3)	C28—H28	0.9300
N4—C20	1.335 (3)	C29—H29	0.9300
N4—C16	1.349 (3)	O1W—H1B	0.8559
C11—C12	1.371 (4)	O1W—H1A	0.8502
C11—H11	0.9300	O2W—H2B	0.8470
C12—C13	1.363 (4)	O2W—H2A	0.8515
C12—H12	0.9300
N1—Cu1—N3	176.27 (8)	C12—C11—H11	118.9
N1—Cu1—N2	80.72 (8)	C13—C12—C11	119.1 (3)
N1—Cu1—O2	93.61 (7)	C13—C12—H12	120.4
N1—Cu1—O1	90.47 (7)	C11—C12—H12	120.4
N1—Cu1—N4	99.06 (8)	C12—C13—C14	119.4 (3)
N2—Cu1—O1	144.88 (7)	C12—C13—H13	120.3
N2—Cu1—N4	111.20 (7)	C14—C13—H13	120.3
N3—Cu1—N2	96.95 (8)	C13—C14—C15	120.0 (3)
N3—Cu1—N4	79.00 (8)	C13—C14—H14	120.0
N3—Cu1—O1	93.09 (7)	C15—C14—H14	120.0
N3—Cu1—O2	89.42 (7)	N3—C15—C14	119.7 (3)
O1—Cu1—O2	53.38 (6)	N3—C15—C16	115.9 (2)
O1—Cu1—N4	103.72 (7)	C14—C15—C16	124.3 (2)
O2—Cu1—N4	154.08 (7)	N4—C16—C17	120.8 (3)
O2—Cu1—N2	93.06 (7)	N4—C16—C15	115.1 (2)
O4—Cl1—O5	111.4 (2)	C17—C16—C15	124.1 (2)
O4—Cl1—O6	110.7 (2)	C18—C17—C16	119.9 (3)
O5—Cl1—O6	107.63 (18)	C18—C17—H17	120.0
O4—Cl1—O7	108.63 (16)	C16—C17—H17	120.0
O5—Cl1—O7	109.92 (16)	C17—C18—C19	119.3 (3)
O6—Cl1—O7	108.53 (17)	C17—C18—H18	120.3
C1—N1—C5	119.3 (2)	C19—C18—H18	120.3
C1—N1—Cu1	125.15 (17)	C18—C19—C20	118.4 (3)
C5—N1—Cu1	115.53 (17)	C18—C19—H19	120.8
C10—N2—C6	118.4 (2)	C20—C19—H19	120.8
C10—N2—Cu1	128.27 (17)	N4—C20—C19	122.9 (3)
C6—N2—Cu1	113.27 (16)	N4—C20—H20	118.5
N1—C1—C2	122.5 (3)	C19—C20—H20	118.5
N1—C1—H1	118.7	C21—O1—Cu1	106.26 (15)
C2—C1—H1	118.7	O1—C21—O2	124.1 (2)
C1—C2—C3	118.3 (3)	O1—C21—C22	119.2 (2)
C1—C2—H2	120.8	O2—C21—C22	116.7 (2)
C3—C2—H2	120.8	N5—C22—C21	115.4 (2)
C4—C3—C2	119.7 (3)	N5—C22—H23	108.4
C4—C3—H3	120.1	C21—C22—H23	108.4
C2—C3—H3	120.1	N5—C22—H22	108.4
C3—C4—C5	119.8 (3)	C21—C22—H22	108.4
C3—C4—H4	120.1	H23—C22—H22	107.5
C5—C4—H4	120.1	C23—N5—C22	121.7 (2)
N1—C5—C4	120.4 (3)	C23—N5—H5	119.1
N1—C5—C6	115.1 (2)	C22—N5—H5	119.1
C4—C5—C6	124.5 (2)	O3—C23—N5	121.0 (2)
N2—C6—C7	121.2 (2)	O3—C23—C24	121.0 (2)
N2—C6—C5	115.1 (2)	N5—C23—C24	118.0 (2)
C7—C6—C5	123.7 (2)	C25—C24—C29	118.6 (2)
C8—C7—C6	119.3 (3)	C25—C24—C23	118.4 (2)
C8—C7—H7	120.3	C29—C24—C23	123.1 (2)
C6—C7—H7	120.3	C26—C25—C24	121.6 (3)
C7—C8—C9	119.5 (3)	C26—C25—H25	119.2
C7—C8—H8	120.3	C24—C25—H25	119.2
C9—C8—H8	120.3	C25—C26—C27	119.6 (3)
C8—C9—C10	118.5 (3)	C25—C26—H26	120.2
C8—C9—H9	120.7	C27—C26—H26	120.2
C10—C9—H9	120.7	C28—C27—C26	119.5 (3)
N2—C10—C9	123.0 (3)	C28—C27—H27	120.2
N2—C10—H10	118.5	C26—C27—H27	120.2
C9—C10—H10	118.5	C27—C28—C29	121.2 (3)
C11—N3—C15	119.5 (2)	C27—C28—H28	119.4
C11—N3—Cu1	123.23 (18)	C29—C28—H28	119.4
C15—N3—Cu1	117.16 (17)	C24—C29—C28	119.5 (3)
C20—N4—C16	118.6 (2)	C24—C29—H29	120.3
C20—N4—Cu1	128.63 (16)	C28—C29—H29	120.3
C16—N4—Cu1	112.72 (16)	H1B—O1W—H1A	103.0
N3—C11—C12	122.1 (3)	H2B—O2W—H2A	112.9
N3—C11—H11	118.9

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
O1W—H1A···O2W	0.85	1.97	2.794 (3)	163
O1W—H1B···O3	0.85	2.27	2.934 (3)	134
O2W—H2A···O3^i	0.85	2.04	2.888 (3)	173
O2W—H2B···O2^ii	0.85	1.91	2.744 (3)	167
N5—H5···O7^iii	0.86	2.22	3.055 (3)	162
C3—H3···O1W^iv	0.93	2.47	3.309 (4)	151
C7—H7···O2^v	0.93	2.40	3.289 (3)	160
C8—H8···O3^v	0.93	2.54	3.469 (3)	173
C22—H22···O4^iii	0.97	2.55	3.362 (5)	141

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