Bis(μ-biphenyl-2,2'-dicarboxyl-ato)bis-[aqua-(4,4'-dimethyl-2,2'-bipyridine-κN,N')copper(II)].

The mol-ecule of the title binuclear copper(II) complex, [Cu(2)(C(14)H(8)O(4))(2)(C(12)H(12)N(2))(2)(H(2)O)(2)], is bis-ected by a crystallographic twofold axis. Each Cu(II) atom is coordinated in a distorted octa-hedral geometry by three O atoms from two biphen-yl-2,2'-dicarboxyl-ate anions, one aqua O atom and two N atoms of a 4,4'-dimethyl-2,2'-bipyridine ligand. Intramolecular O-H⋯O hydrogen bonds between the coordinated water molecules and the carboxylate O atoms are also present.

Related literature

For related structures, see: Li et al. (2009 ▶); Jiang & Feng (2009 ▶); Xu et al. (2009 ▶); Zhang et al. (2009 ▶); Rizal & Ng (2009 ▶); Zhang (2009 ▶).

Experimental

Crystal data

[Cu2(C14H8O4)2(C12H12N2)2(H2O)2]

M = 1109.71

Monoclinic,

a = 17.104 (3) Å

b = 15.395 (2) Å

c = 18.289 (3) Å

β = 104.413 (3)°

V = 4664.2 (13) Å3

Z = 4

Mo Kα radiation

μ = 0.98 mm−1

T = 296 K

0.26 × 0.24 × 0.22 mm

Data collection

Bruker SMART APEXII CCD area-detector diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2005 ▶) T min = 0.785, T max = 0.814

13512 measured reflections

4594 independent reflections

3108 reflections with I > 2σ(I)

R int = 0.060

Refinement

R[F 2 > 2σ(F 2)] = 0.047

wR(F 2) = 0.109

S = 0.93

4594 reflections

310 parameters

12 restraints

H-atom parameters constrained

Δρmax = 0.87 e Å−3

Δρmin = −0.33 e Å−3

Data collection: APEX2 (Bruker, 2005 ▶); cell refinement: SAINT (Bruker, 2005 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: SHELXTL (Sheldrick, 2008 ▶); software used to prepare material for publication: SHELXTL.

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536809040628/jh2107sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536809040628/jh2107Isup2.hkl

Additional supplementary materials: crystallographic information; 3D view; checkCIF report

[Cu2(C14H8O4)2(C12H12N2)2(H2O)2]	F(000) = 2240
Mr = 1109.71	Dx = 1.580 Mg m−3
Monoclinic, C2/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -C 2yc	Cell parameters from 3688 reflections
a = 17.104 (3) Å	θ = 2.7–27.3°
b = 15.395 (2) Å	µ = 0.98 mm−1
c = 18.289 (3) Å	T = 296 K
β = 104.413 (3)°	Block, colourless
V = 4664.2 (13) Å3	0.26 × 0.24 × 0.22 mm
Z = 4

Bruker SMART APEXII CCD area-detector diffractometer	4594 independent reflections
Radiation source: fine-focus sealed tube	3108 reflections with I > 2σ(I)
graphite	Rint = 0.060
φ and ω scans	θmax = 26.0°, θmin = 1.8°
Absorption correction: multi-scan (SADABS; Bruker, 2005)	h = −21→20
Tmin = 0.785, Tmax = 0.814	k = −18→12
13512 measured reflections	l = −22→22

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)] = 0.047	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.109	H-atom parameters constrained
S = 0.93	w = 1/[σ2(Fo2) + (0.0562P)2] where P = (Fo2 + 2Fc2)/3
4594 reflections	(Δ/σ)max = 0.001
310 parameters	Δρmax = 0.87 e Å−3
12 restraints	Δρmin = −0.33 e Å−3

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.

	x	y	z	Uiso*/Ueq
Cd1	0.13088 (2)	0.599652 (19)	0.344239 (17)	0.05361 (14)
N1	0.1810 (2)	0.5542 (2)	0.4686 (2)	0.0615 (10)
N2	0.2592 (2)	0.6574 (2)	0.39215 (19)	0.0516 (9)
O1	0.11652 (18)	0.67905 (18)	0.23068 (16)	0.0602 (8)
O2	0.0871 (2)	0.74927 (19)	0.32546 (17)	0.0611 (8)
O3	0.1387 (2)	0.4729 (2)	0.2927 (3)	0.0977 (12)
O4	0.0538 (2)	0.41826 (19)	0.1917 (2)	0.0701 (10)
O1W	0.00362 (18)	0.57274 (19)	0.35468 (17)	0.0611 (8)
H1WA	−0.0326	0.6100	0.3365	0.073*
H1WB	−0.0137	0.5234	0.3371	0.073*
C1	0.0942 (3)	0.7474 (3)	0.2590 (3)	0.0527 (11)
C2	0.0782 (3)	0.8273 (3)	0.2111 (2)	0.0537 (11)
C3	0.1193 (3)	0.8370 (3)	0.1546 (3)	0.0677 (14)
H3	0.1545	0.7937	0.1473	0.081*
C4	0.1087 (4)	0.9095 (3)	0.1096 (3)	0.0825 (17)
H4	0.1387	0.9161	0.0740	0.099*
C5	0.0541 (4)	0.9725 (3)	0.1166 (3)	0.0813 (16)
H5	0.0455	1.0205	0.0848	0.098*
C6	0.0121 (3)	0.9632 (3)	0.1716 (3)	0.0685 (14)
H6	−0.0245	1.0060	0.1769	0.082*
C7	0.0232 (3)	0.8913 (2)	0.2195 (3)	0.0540 (11)
C8	0.0959 (3)	0.4138 (3)	0.2577 (4)	0.0675 (15)
C9	0.0975 (3)	0.3293 (3)	0.3005 (3)	0.0578 (12)
C10	0.1638 (4)	0.3135 (4)	0.3615 (4)	0.0935 (19)
H10	0.2047	0.3546	0.3747	0.112*
C11	0.1687 (5)	0.2361 (5)	0.4026 (4)	0.114 (2)
H11	0.2144	0.2245	0.4411	0.137*
C12	0.1072 (5)	0.1780 (4)	0.3865 (4)	0.101 (2)
H12	0.1096	0.1276	0.4151	0.121*
C13	0.0428 (3)	0.1938 (3)	0.3290 (3)	0.0691 (14)
H13	0.0007	0.1538	0.3194	0.083*
C14	0.0357 (3)	0.2671 (2)	0.2827 (2)	0.0491 (10)
C15	0.2960 (3)	0.7114 (3)	0.3534 (2)	0.0619 (12)
H15	0.2725	0.7195	0.3023	0.074*
C16	0.3658 (3)	0.7551 (3)	0.3848 (3)	0.0577 (12)
H16	0.3882	0.7925	0.3556	0.069*
C17	0.4026 (3)	0.7432 (3)	0.4598 (2)	0.0523 (11)
C18	0.3652 (3)	0.6872 (3)	0.4998 (2)	0.0514 (11)
H18	0.3882	0.6778	0.5508	0.062*
C19	0.2946 (3)	0.6456 (2)	0.4655 (2)	0.0446 (10)
C20	0.2522 (3)	0.5850 (2)	0.5076 (3)	0.0484 (11)
C21	0.2842 (3)	0.5611 (3)	0.5819 (3)	0.0575 (12)
H21	0.3336	0.5840	0.6080	0.069*
C22	0.2441 (3)	0.5040 (3)	0.6179 (3)	0.0589 (12)
C23	0.1719 (3)	0.4713 (3)	0.5762 (3)	0.0750 (15)
H23	0.1435	0.4311	0.5974	0.090*
C24	0.1423 (3)	0.4981 (3)	0.5035 (3)	0.0761 (15)
H24	0.0927	0.4763	0.4766	0.091*
C25	0.4800 (3)	0.7895 (3)	0.4962 (3)	0.0717 (14)
H25A	0.4703	0.8509	0.4960	0.108*
H25B	0.5196	0.7774	0.4685	0.108*
H25C	0.4994	0.7698	0.5473	0.108*
C26	0.2776 (3)	0.4777 (4)	0.6985 (3)	0.0843 (16)
H26A	0.3136	0.4294	0.7006	0.126*
H26B	0.2342	0.4612	0.7203	0.126*
H26C	0.3066	0.5256	0.7263	0.126*

	U11	U22	U33	U12	U13	U23
Cd1	0.0639 (3)	0.0397 (2)	0.0639 (2)	−0.00834 (15)	0.02867 (18)	−0.00204 (16)
N1	0.068 (3)	0.050 (2)	0.073 (3)	−0.012 (2)	0.031 (2)	0.012 (2)
N2	0.062 (2)	0.044 (2)	0.057 (2)	−0.0098 (17)	0.0290 (18)	0.0006 (17)
O1	0.074 (2)	0.0420 (17)	0.073 (2)	0.0006 (15)	0.0356 (17)	−0.0078 (15)
O2	0.078 (2)	0.0476 (17)	0.068 (2)	0.0056 (15)	0.0378 (17)	0.0039 (15)
O3	0.087 (2)	0.070 (2)	0.150 (3)	−0.021 (2)	0.057 (2)	−0.040 (2)
O4	0.084 (3)	0.0377 (18)	0.106 (3)	−0.0016 (17)	0.058 (2)	−0.0019 (19)
O1W	0.065 (2)	0.0444 (16)	0.080 (2)	−0.0043 (15)	0.0306 (17)	−0.0008 (16)
C1	0.055 (3)	0.039 (2)	0.073 (3)	−0.0036 (19)	0.033 (2)	0.001 (2)
C2	0.063 (3)	0.042 (2)	0.065 (3)	−0.007 (2)	0.032 (2)	−0.002 (2)
C3	0.082 (4)	0.054 (3)	0.080 (3)	−0.004 (3)	0.045 (3)	0.003 (3)
C4	0.113 (5)	0.073 (4)	0.078 (4)	−0.014 (3)	0.054 (3)	0.009 (3)
C5	0.115 (5)	0.050 (3)	0.087 (4)	−0.005 (3)	0.040 (3)	0.017 (3)
C6	0.088 (4)	0.041 (3)	0.083 (3)	−0.002 (2)	0.035 (3)	0.008 (2)
C7	0.063 (3)	0.035 (2)	0.068 (3)	−0.005 (2)	0.025 (2)	0.000 (2)
C8	0.062 (3)	0.044 (3)	0.116 (5)	−0.009 (2)	0.057 (3)	−0.029 (3)
C9	0.058 (3)	0.053 (3)	0.069 (3)	0.005 (2)	0.027 (2)	−0.026 (2)
C10	0.067 (4)	0.093 (5)	0.117 (5)	0.003 (3)	0.017 (4)	−0.044 (4)
C11	0.116 (5)	0.116 (5)	0.093 (4)	0.045 (5)	−0.008 (4)	−0.020 (4)
C12	0.125 (6)	0.089 (5)	0.082 (4)	0.030 (4)	0.013 (4)	−0.001 (4)
C13	0.090 (4)	0.052 (3)	0.069 (3)	0.017 (3)	0.026 (3)	0.003 (3)
C14	0.061 (3)	0.035 (2)	0.058 (3)	0.0070 (19)	0.0269 (19)	−0.0053 (19)
C15	0.072 (3)	0.065 (3)	0.055 (3)	−0.009 (3)	0.029 (2)	0.012 (2)
C16	0.066 (3)	0.049 (3)	0.068 (3)	−0.010 (2)	0.037 (3)	0.008 (2)
C17	0.066 (3)	0.036 (2)	0.065 (3)	−0.003 (2)	0.036 (2)	−0.004 (2)
C18	0.062 (3)	0.047 (2)	0.052 (2)	−0.003 (2)	0.027 (2)	−0.003 (2)
C19	0.056 (3)	0.032 (2)	0.055 (3)	0.0018 (19)	0.031 (2)	−0.0006 (19)
C20	0.056 (3)	0.036 (2)	0.062 (3)	0.0020 (19)	0.032 (2)	0.001 (2)
C21	0.066 (3)	0.052 (3)	0.064 (3)	−0.001 (2)	0.034 (2)	0.008 (2)
C22	0.069 (3)	0.054 (3)	0.068 (3)	0.006 (2)	0.042 (3)	0.010 (2)
C23	0.083 (4)	0.068 (3)	0.087 (4)	−0.013 (3)	0.045 (3)	0.025 (3)
C24	0.068 (3)	0.070 (3)	0.096 (4)	−0.016 (3)	0.030 (3)	0.020 (3)
C25	0.077 (4)	0.068 (3)	0.077 (3)	−0.023 (3)	0.033 (3)	−0.007 (3)
C26	0.106 (4)	0.083 (4)	0.079 (4)	−0.003 (3)	0.050 (3)	0.022 (3)

Cd1—O3	2.186 (4)	C10—H10	0.9300
Cd1—O1W	2.270 (3)	C11—C12	1.357 (9)
Cd1—N2	2.327 (3)	C11—H11	0.9300
Cd1—N1	2.329 (4)	C12—C13	1.342 (8)
Cd1—O1	2.369 (3)	C12—H12	0.9300
Cd1—O2	2.420 (3)	C13—C14	1.397 (6)
N1—C20	1.335 (6)	C13—H13	0.9300
N1—C24	1.343 (5)	C14—C14i	1.482 (8)
N2—C19	1.339 (5)	C15—C16	1.366 (6)
N2—C15	1.346 (5)	C15—H15	0.9300
O1—C1	1.272 (5)	C16—C17	1.371 (6)
O2—C1	1.252 (5)	C16—H16	0.9300
O3—C8	1.240 (6)	C17—C18	1.386 (5)
O4—C8	1.244 (6)	C17—C25	1.505 (6)
O1W—H1WA	0.8498	C18—C19	1.373 (6)
O1W—H1WB	0.8499	C18—H18	0.9300
C1—C2	1.495 (6)	C19—C20	1.506 (5)
C2—C3	1.395 (6)	C20—C21	1.382 (6)
C2—C7	1.397 (6)	C21—C22	1.380 (6)
C3—C4	1.372 (6)	C21—H21	0.9300
C3—H3	0.9300	C22—C23	1.375 (7)
C4—C5	1.374 (7)	C22—C26	1.499 (6)
C4—H4	0.9300	C23—C24	1.364 (7)
C5—C6	1.382 (7)	C23—H23	0.9300
C5—H5	0.9300	C24—H24	0.9300
C6—C7	1.394 (6)	C25—H25A	0.9600
C6—H6	0.9300	C25—H25B	0.9600
C7—C7i	1.524 (8)	C25—H25C	0.9600
C8—C9	1.515 (7)	C26—H26A	0.9600
C9—C10	1.400 (8)	C26—H26B	0.9600
C9—C14	1.403 (6)	C26—H26C	0.9600
C10—C11	1.400 (9)
O3—Cd1—O1W	92.06 (12)	C9—C10—H10	119.9
O3—Cd1—N2	110.50 (13)	C12—C11—C10	120.3 (6)
O1W—Cd1—N2	150.70 (11)	C12—C11—H11	119.8
O3—Cd1—N1	96.06 (15)	C10—C11—H11	119.8
O1W—Cd1—N1	89.48 (12)	C13—C12—C11	119.4 (6)
N2—Cd1—N1	70.32 (12)	C13—C12—H12	120.3
O3—Cd1—O1	95.00 (13)	C11—C12—H12	120.3
O1W—Cd1—O1	106.00 (11)	C12—C13—C14	123.5 (6)
N2—Cd1—O1	90.88 (11)	C12—C13—H13	118.2
N1—Cd1—O1	160.61 (12)	C14—C13—H13	118.2
O3—Cd1—O2	147.01 (15)	C13—C14—C9	117.6 (4)
O1W—Cd1—O2	85.21 (10)	C13—C14—C14i	114.8 (4)
N2—Cd1—O2	85.37 (12)	C9—C14—C14i	127.5 (3)
N1—Cd1—O2	116.74 (12)	N2—C15—C16	123.9 (4)
O1—Cd1—O2	54.80 (9)	N2—C15—H15	118.0
C20—N1—C24	117.8 (4)	C16—C15—H15	118.0
C20—N1—Cd1	118.7 (3)	C15—C16—C17	119.3 (4)
C24—N1—Cd1	123.5 (4)	C15—C16—H16	120.4
C19—N2—C15	117.1 (4)	C17—C16—H16	120.4
C19—N2—Cd1	118.3 (2)	C16—C17—C18	117.0 (4)
C15—N2—Cd1	124.0 (3)	C16—C17—C25	120.9 (4)
C1—O1—Cd1	92.7 (2)	C18—C17—C25	122.1 (4)
C1—O2—Cd1	90.8 (2)	C19—C18—C17	121.2 (4)
C8—O3—Cd1	141.8 (3)	C19—C18—H18	119.4
Cd1—O1W—H1WA	117.7	C17—C18—H18	119.4
Cd1—O1W—H1WB	112.5	N2—C19—C18	121.5 (4)
H1WA—O1W—H1WB	107.7	N2—C19—C20	116.1 (4)
O2—C1—O1	121.7 (4)	C18—C19—C20	122.4 (4)
O2—C1—C2	120.2 (4)	N1—C20—C21	121.1 (4)
O1—C1—C2	118.1 (4)	N1—C20—C19	115.9 (4)
C3—C2—C7	118.8 (4)	C21—C20—C19	123.0 (4)
C3—C2—C1	118.0 (4)	C22—C21—C20	121.1 (5)
C7—C2—C1	123.1 (4)	C22—C21—H21	119.5
C4—C3—C2	121.1 (5)	C20—C21—H21	119.5
C4—C3—H3	119.5	C23—C22—C21	116.9 (4)
C2—C3—H3	119.5	C23—C22—C26	121.2 (4)
C3—C4—C5	120.7 (5)	C21—C22—C26	121.9 (5)
C3—C4—H4	119.7	C24—C23—C22	119.7 (4)
C5—C4—H4	119.7	C24—C23—H23	120.2
C4—C5—C6	119.0 (5)	C22—C23—H23	120.2
C4—C5—H5	120.5	N1—C24—C23	123.4 (5)
C6—C5—H5	120.5	N1—C24—H24	118.3
C5—C6—C7	121.6 (5)	C23—C24—H24	118.3
C5—C6—H6	119.2	C17—C25—H25A	109.5
C7—C6—H6	119.2	C17—C25—H25B	109.5
C6—C7—C2	118.8 (4)	H25A—C25—H25B	109.5
C6—C7—C7i	116.4 (3)	C17—C25—H25C	109.5
C2—C7—C7i	124.6 (3)	H25A—C25—H25C	109.5
O3—C8—O4	125.9 (6)	H25B—C25—H25C	109.5
O3—C8—C9	115.5 (6)	C22—C26—H26A	109.5
O4—C8—C9	118.7 (4)	C22—C26—H26B	109.5
C10—C9—C14	118.7 (5)	H26A—C26—H26B	109.5
C10—C9—C8	117.9 (5)	C22—C26—H26C	109.5
C14—C9—C8	123.5 (4)	H26A—C26—H26C	109.5
C11—C10—C9	120.3 (6)	H26B—C26—H26C	109.5
C11—C10—H10	119.9
O3—Cd1—N1—C20	113.7 (3)	C1—C2—C7—C6	−179.5 (4)
O1W—Cd1—N1—C20	−154.3 (3)	C3—C2—C7—C7i	−177.3 (5)
N2—Cd1—N1—C20	4.0 (3)	C1—C2—C7—C7i	3.9 (8)
O1—Cd1—N1—C20	−10.8 (6)	Cd1—O3—C8—O4	69.7 (8)
O2—Cd1—N1—C20	−69.9 (3)	Cd1—O3—C8—C9	−111.2 (6)
O3—Cd1—N1—C24	−65.9 (4)	O3—C8—C9—C10	−21.7 (6)
O1W—Cd1—N1—C24	26.1 (4)	O4—C8—C9—C10	157.6 (4)
N2—Cd1—N1—C24	−175.6 (4)	O3—C8—C9—C14	157.5 (4)
O1—Cd1—N1—C24	169.6 (3)	O4—C8—C9—C14	−23.3 (6)
O2—Cd1—N1—C24	110.5 (4)	C14—C9—C10—C11	1.4 (7)
O3—Cd1—N2—C19	−95.8 (3)	C8—C9—C10—C11	−179.4 (5)
O1W—Cd1—N2—C19	42.3 (4)	C9—C10—C11—C12	−3.8 (10)
N1—Cd1—N2—C19	−6.6 (3)	C10—C11—C12—C13	2.4 (10)
O1—Cd1—N2—C19	168.5 (3)	C11—C12—C13—C14	1.3 (9)
O2—Cd1—N2—C19	114.0 (3)	C12—C13—C14—C9	−3.6 (7)
O3—Cd1—N2—C15	93.2 (4)	C12—C13—C14—C14i	173.3 (5)
O1W—Cd1—N2—C15	−128.7 (3)	C10—C9—C14—C13	2.1 (6)
N1—Cd1—N2—C15	−177.6 (4)	C8—C9—C14—C13	−177.0 (4)
O1—Cd1—N2—C15	−2.5 (3)	C10—C9—C14—C14i	−174.3 (5)
O2—Cd1—N2—C15	−57.1 (3)	C8—C9—C14—C14i	6.5 (7)
O3—Cd1—O1—C1	166.2 (3)	C19—N2—C15—C16	−1.0 (7)
O1W—Cd1—O1—C1	72.6 (3)	Cd1—N2—C15—C16	170.2 (4)
N2—Cd1—O1—C1	−83.1 (3)	N2—C15—C16—C17	1.1 (7)
N1—Cd1—O1—C1	−69.2 (4)	C15—C16—C17—C18	−0.7 (6)
O2—Cd1—O1—C1	0.6 (2)	C15—C16—C17—C25	179.5 (4)
O3—Cd1—O2—C1	−27.6 (4)	C16—C17—C18—C19	0.2 (6)
O1W—Cd1—O2—C1	−114.0 (3)	C25—C17—C18—C19	−180.0 (4)
N2—Cd1—O2—C1	93.8 (3)	C15—N2—C19—C18	0.4 (6)
N1—Cd1—O2—C1	159.0 (3)	Cd1—N2—C19—C18	−171.2 (3)
O1—Cd1—O2—C1	−0.6 (2)	C15—N2—C19—C20	179.9 (4)
O1W—Cd1—O3—C8	22.1 (7)	Cd1—N2—C19—C20	8.3 (4)
N2—Cd1—O3—C8	−177.0 (7)	C17—C18—C19—N2	−0.1 (6)
N1—Cd1—O3—C8	111.8 (7)	C17—C18—C19—C20	−179.5 (4)
O1—Cd1—O3—C8	−84.2 (7)	C24—N1—C20—C21	−1.3 (6)
O2—Cd1—O3—C8	−62.3 (8)	Cd1—N1—C20—C21	179.0 (3)
Cd1—O2—C1—O1	1.1 (4)	C24—N1—C20—C19	178.2 (4)
Cd1—O2—C1—C2	−177.5 (4)	Cd1—N1—C20—C19	−1.4 (5)
Cd1—O1—C1—O2	−1.1 (4)	N2—C19—C20—N1	−4.5 (5)
Cd1—O1—C1—C2	177.5 (3)	C18—C19—C20—N1	175.0 (4)
O2—C1—C2—C3	151.3 (4)	N2—C19—C20—C21	175.0 (4)
O1—C1—C2—C3	−27.4 (6)	C18—C19—C20—C21	−5.5 (6)
O2—C1—C2—C7	−29.9 (7)	N1—C20—C21—C22	0.8 (6)
O1—C1—C2—C7	151.5 (4)	C19—C20—C21—C22	−178.7 (4)
C7—C2—C3—C4	2.4 (8)	C20—C21—C22—C23	1.0 (7)
C1—C2—C3—C4	−178.7 (5)	C20—C21—C22—C26	−179.8 (4)
C2—C3—C4—C5	−3.3 (8)	C21—C22—C23—C24	−2.1 (7)
C3—C4—C5—C6	2.4 (9)	C26—C22—C23—C24	178.6 (5)
C4—C5—C6—C7	−0.7 (9)	C20—N1—C24—C23	0.1 (7)
C5—C6—C7—C2	−0.1 (8)	Cd1—N1—C24—C23	179.7 (4)
C5—C6—C7—C7i	176.7 (5)	C22—C23—C24—N1	1.7 (8)
C3—C2—C7—C6	−0.7 (7)

D—H···A	D—H	H···A	D···A	D—H···A
O1W—H1WB···O4i	0.85	1.78	2.632 (4)	174
O1W—H1WA···O1i	0.85	1.95	2.782 (4)	164

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O1W—H1WB⋯O4i	0.85	1.78	2.632 (4)	174
O1W—H1WA⋯O1i	0.85	1.95	2.782 (4)	164

Symmetry code: (i) .