catena-Poly[[[aqua-copper(II)]bis-[μ-bis(3,5-dimethyl-1H-pyrazol-4-yl) selenide]] bis-(tetra-fluorido-borate) bis-(triphenyl-phosphine oxide) monohydrate].

The title compound, {[Cu(C(10)H(14)N(4)Se)(2)(H(2)O)](BF(4))(2)·2C(18)H(15)PO·H(2)O}(n), has a polymeric structure where each Cu(II) ion adopts a square-pyramidal coordination constituted by four N atoms of pyrazole moieties in the equatorial plane and an axial O atom of a water mol-ecule. A pair of bis-(3,5-dimethyl-1H-pyrazol-4-yl) selenide ligands bridges the Cu(II) centres into a chain extending along the c axis. The water mol-ecules, anions and triphenyl-phosphine oxide mol-ecules are involved in inter-molecular hydrogen bonding, which links the chains into a three-dimensional network.

Related literature

For general background, see: Farha et al. (2009 ▶); Shibahara et al. (2007 ▶); Zhang et al. (2009 ▶). For related structures, see: Seredyuk et al. (2007 ▶, 2009 ▶).

Experimental

Crystal data

[Cu(C10H14N4Se)2(H2O)](BF4)2·2C18H15OP·H2O

M = 1386.17

Monoclinic,

a = 21.4560 (4) Å

b = 15.3590 (4) Å

c = 18.4910 (6) Å

β = 97.74 (2)°

V = 6038.0 (3) Å3

Z = 4

Mo Kα radiation

μ = 1.70 mm−1

T = 100 K

0.09 × 0.07 × 0.04 mm

Data collection

Kuma KM4 CCD area-detector diffractometer

34362 measured reflections

6876 independent reflections

6210 reflections with I > 2σ(I)

R int = 0.045

Refinement

R[F 2 > 2σ(F 2)] = 0.043

wR(F 2) = 0.082

S = 1.16

6876 reflections

384 parameters

H-atom parameters constrained

Δρmax = 0.63 e Å−3

Δρmin = −0.38 e Å−3

Data collection: KM-4-CCD (Kuma, 1999 ▶); cell refinement: KM-4-CCD; data reduction: KM-4-CCD; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997 ▶); software used to prepare material for publication: WinGX (Farrugia, 1999 ▶).

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536810012997/ds2023sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536810012997/ds2023Isup2.hkl

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

[Cu(C10H14N4Se)2(H2O)](BF4)2·2C18H15OP·H2O	F(000) = 2820
Mr = 1386.17	Dx = 1.525 Mg m−3
Monoclinic, C2/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -C 2yc	Cell parameters from 34362 reflections
a = 21.4560 (4) Å	θ = 3.1–28.5°
b = 15.3590 (4) Å	µ = 1.70 mm−1
c = 18.4910 (6) Å	T = 100 K
β = 97.74 (2)°	Needle, green
V = 6038.0 (3) Å3	0.09 × 0.07 × 0.04 mm
Z = 4

Kuma KM4 CCD area-detector diffractometer	6210 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	Rint = 0.045
graphite	θmax = 27.5°, θmin = 3.1°
ω scans	h = −27→27
34362 measured reflections	k = −19→18
6876 independent reflections	l = −24→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)] = 0.043	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.082	H-atom parameters constrained
S = 1.16	w = 1/[σ2(Fo2) + (0.0323P)2 + 9.8106P] where P = (Fo2 + 2Fc2)/3
6876 reflections	(Δ/σ)max = 0.002
384 parameters	Δρmax = 0.63 e Å−3
0 restraints	Δρmin = −0.38 e Å−3

Experimental. The H atoms were located from the difference Fourier map and were constrained to ride on their parent atoms with Uiso = 1.2–1.5Ueq(parent atom). The highest peak is located 0.90 Å from atom F3 and the deepest hole is located 0.67 Å from atom F2.

Geometry. All s.u.'s (except the s.u. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell s.u.'s are taken into account individually in the estimation of s.u.'s in distances, angles and torsion angles; correlations between s.u.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell s.u.'s is used for estimating s.u.'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 > 2σ(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
C1	0.76965 (12)	0.52259 (18)	0.58609 (14)	0.0230 (6)
H1A	0.7463	0.4882	0.6180	0.035*
H1B	0.7520	0.5126	0.5351	0.035*
H1C	0.7664	0.5845	0.5977	0.035*
C2	0.83728 (11)	0.49578 (16)	0.59738 (12)	0.0161 (5)
C3	0.87223 (11)	0.44383 (15)	0.55608 (12)	0.0150 (5)
C4	0.93294 (11)	0.43713 (15)	0.59578 (12)	0.0140 (5)
C5	0.98757 (11)	0.38947 (16)	0.57328 (13)	0.0163 (5)
H5A	1.0132	0.4296	0.5485	0.025*
H5B	0.9724	0.3421	0.5400	0.025*
H5C	1.0131	0.3653	0.6165	0.025*
C6	0.97077 (12)	0.35740 (16)	0.37061 (14)	0.0199 (5)
H6A	0.9845	0.3431	0.3236	0.030*
H6B	0.9494	0.3070	0.3885	0.030*
H6C	1.0075	0.3725	0.4059	0.030*
C7	0.92668 (11)	0.43281 (15)	0.36128 (12)	0.0142 (5)
C8	0.87522 (11)	0.45220 (15)	0.39826 (12)	0.0134 (5)
C9	0.84777 (11)	0.52685 (16)	0.36613 (12)	0.0156 (5)
C10	0.78973 (12)	0.57463 (17)	0.37889 (14)	0.0207 (5)
H10A	0.7855	0.6274	0.3489	0.031*
H10B	0.7926	0.5906	0.4305	0.031*
H10C	0.7530	0.5372	0.3656	0.031*
C11	0.93216 (12)	0.04009 (16)	0.84170 (13)	0.0172 (5)
C12	0.97655 (13)	−0.02714 (16)	0.84964 (13)	0.0204 (5)
H12	1.0177	−0.0166	0.8740	0.024*
C13	0.96033 (14)	−0.10957 (17)	0.82184 (15)	0.0264 (6)
H13	0.9906	−0.1551	0.8269	0.032*
C14	0.90039 (15)	−0.12532 (19)	0.78687 (15)	0.0326 (7)
H14	0.8894	−0.1818	0.7683	0.039*
C15	0.85628 (15)	−0.0592 (2)	0.77881 (15)	0.0328 (7)
H15	0.8151	−0.0704	0.7547	0.039*
C16	0.87171 (13)	0.02374 (18)	0.80581 (14)	0.0252 (6)
H16	0.8413	0.0690	0.7999	0.030*
C17	0.89479 (12)	0.09403 (16)	0.99831 (13)	0.0192 (5)
H17	0.9065	0.0365	0.9869	0.023*
C18	0.86575 (12)	0.10921 (18)	1.06015 (14)	0.0234 (6)
H18	0.8580	0.0620	1.0909	0.028*
C19	0.84825 (13)	0.19234 (19)	1.07704 (15)	0.0263 (6)
H19	0.8285	0.2024	1.1193	0.032*
C20	0.90673 (11)	0.16311 (15)	0.95319 (13)	0.0151 (5)
C21	1.07652 (13)	0.14666 (17)	0.86366 (15)	0.0234 (6)
H21	1.0631	0.1465	0.8126	0.028*
C22	1.11652 (13)	0.14863 (17)	1.01317 (15)	0.0236 (6)
H22	1.1304	0.1496	1.0642	0.028*
C23	1.05261 (12)	0.14969 (16)	0.98780 (13)	0.0183 (5)
H23	1.0228	0.1510	1.0215	0.022*
C24	1.03194 (12)	0.14881 (15)	0.91255 (13)	0.0160 (5)
C25	1.16016 (13)	0.14610 (17)	0.96428 (16)	0.0262 (6)
H25	1.2038	0.1453	0.9819	0.031*
C26	0.88851 (13)	0.24716 (17)	0.97001 (15)	0.0244 (6)
H26	0.8959	0.2945	0.9392	0.029*
C27	0.85963 (14)	0.26146 (19)	1.03183 (16)	0.0311 (7)
H27	0.8476	0.3188	1.0434	0.037*
C28	1.14020 (13)	0.14472 (19)	0.88991 (16)	0.0283 (6)
H28	1.1703	0.1424	0.8567	0.034*
N1	0.87644 (9)	0.51791 (13)	0.65756 (10)	0.0159 (4)
H1N	0.8655	0.5510	0.6926	0.019*
N2	0.93546 (9)	0.48303 (13)	0.65830 (10)	0.0132 (4)
N3	0.93111 (9)	0.49421 (12)	0.30991 (10)	0.0130 (4)
N4	0.88268 (9)	0.55081 (13)	0.31437 (10)	0.0140 (4)
H4N	0.8752	0.5973	0.2867	0.017*
O1	1.0000	0.33717 (15)	0.7500	0.0184 (5)
H1O	0.9810	0.3047	0.7736	0.028*
O2	0.93330 (8)	0.21702 (11)	0.81896 (9)	0.0200 (4)
O1W	0.84524 (9)	0.31134 (11)	0.72590 (10)	0.0238 (4)
H1W	0.8041	0.2973	0.7207	0.036*
H2W	0.8687	0.2652	0.7505	0.036*
Cu1	1.0000	0.48181 (3)	0.7500	0.01134 (9)
Se1	0.841882 (11)	0.382203 (16)	0.468941 (12)	0.01567 (7)
P1	0.94959 (3)	0.14841 (4)	0.87644 (3)	0.01450 (13)
B1	0.71450 (15)	0.1759 (2)	0.75026 (17)	0.0261 (7)
F4	0.65217 (8)	0.17089 (10)	0.76495 (9)	0.0292 (4)
F3	0.75223 (9)	0.21024 (12)	0.81081 (10)	0.0423 (5)
F1	0.73540 (9)	0.09284 (12)	0.73760 (10)	0.0459 (5)
F2	0.71809 (9)	0.22853 (14)	0.68996 (10)	0.0503 (5)

	U11	U22	U33	U12	U13	U23
C1	0.0159 (13)	0.0333 (15)	0.0200 (13)	0.0052 (11)	0.0030 (10)	−0.0026 (11)
C2	0.0145 (12)	0.0212 (12)	0.0127 (11)	0.0000 (10)	0.0028 (9)	0.0022 (9)
C3	0.0155 (12)	0.0189 (12)	0.0111 (11)	−0.0018 (9)	0.0037 (9)	0.0021 (9)
C4	0.0172 (12)	0.0148 (11)	0.0107 (11)	−0.0012 (9)	0.0045 (9)	0.0027 (9)
C5	0.0153 (12)	0.0201 (12)	0.0134 (11)	0.0030 (10)	0.0014 (9)	−0.0025 (9)
C6	0.0209 (13)	0.0201 (13)	0.0197 (12)	0.0031 (10)	0.0064 (10)	0.0033 (10)
C7	0.0136 (12)	0.0179 (12)	0.0111 (11)	−0.0026 (9)	0.0016 (9)	−0.0020 (9)
C8	0.0115 (11)	0.0179 (12)	0.0107 (10)	−0.0023 (9)	0.0015 (9)	−0.0026 (9)
C9	0.0154 (12)	0.0197 (12)	0.0116 (11)	−0.0007 (10)	0.0019 (9)	−0.0018 (9)
C10	0.0175 (13)	0.0262 (14)	0.0191 (12)	0.0042 (10)	0.0045 (10)	−0.0011 (10)
C11	0.0211 (13)	0.0197 (12)	0.0118 (11)	−0.0025 (10)	0.0053 (9)	0.0012 (9)
C12	0.0236 (14)	0.0201 (13)	0.0184 (12)	−0.0010 (10)	0.0062 (10)	0.0004 (10)
C13	0.0363 (16)	0.0205 (13)	0.0245 (13)	−0.0015 (12)	0.0119 (12)	−0.0022 (11)
C14	0.048 (2)	0.0277 (15)	0.0234 (14)	−0.0133 (14)	0.0115 (13)	−0.0091 (12)
C15	0.0329 (17)	0.0432 (18)	0.0210 (14)	−0.0154 (14)	−0.0015 (12)	−0.0022 (12)
C16	0.0229 (14)	0.0309 (15)	0.0213 (13)	−0.0015 (11)	0.0017 (11)	0.0016 (11)
C17	0.0187 (13)	0.0180 (12)	0.0218 (13)	0.0002 (10)	0.0063 (10)	0.0014 (10)
C18	0.0212 (14)	0.0280 (14)	0.0223 (13)	−0.0012 (11)	0.0078 (11)	0.0063 (11)
C19	0.0238 (14)	0.0356 (16)	0.0217 (13)	−0.0007 (12)	0.0114 (11)	−0.0048 (11)
C20	0.0120 (11)	0.0172 (12)	0.0164 (11)	0.0012 (9)	0.0030 (9)	0.0016 (9)
C21	0.0234 (14)	0.0269 (14)	0.0213 (13)	0.0021 (11)	0.0084 (11)	0.0038 (11)
C22	0.0214 (14)	0.0227 (13)	0.0252 (14)	0.0010 (11)	−0.0020 (11)	0.0023 (11)
C23	0.0180 (13)	0.0175 (12)	0.0201 (12)	0.0005 (10)	0.0056 (10)	0.0008 (9)
C24	0.0166 (12)	0.0127 (11)	0.0194 (12)	0.0010 (9)	0.0045 (10)	0.0016 (9)
C25	0.0141 (13)	0.0231 (13)	0.0408 (16)	0.0011 (10)	0.0019 (11)	0.0076 (12)
C26	0.0254 (14)	0.0187 (13)	0.0318 (15)	0.0015 (11)	0.0140 (12)	0.0033 (11)
C27	0.0348 (17)	0.0221 (14)	0.0398 (17)	0.0035 (12)	0.0177 (14)	−0.0056 (12)
C28	0.0199 (14)	0.0318 (15)	0.0359 (16)	0.0044 (11)	0.0137 (12)	0.0100 (12)
N1	0.0150 (10)	0.0210 (10)	0.0121 (9)	0.0046 (8)	0.0032 (8)	−0.0002 (8)
N2	0.0113 (10)	0.0175 (10)	0.0113 (9)	0.0021 (8)	0.0029 (7)	0.0013 (7)
N3	0.0120 (10)	0.0157 (10)	0.0114 (9)	0.0017 (8)	0.0018 (7)	0.0006 (7)
N4	0.0138 (10)	0.0151 (10)	0.0135 (9)	0.0026 (8)	0.0028 (8)	0.0017 (7)
O1	0.0212 (13)	0.0162 (12)	0.0203 (12)	0.000	0.0111 (10)	0.000
O2	0.0196 (9)	0.0212 (9)	0.0195 (9)	0.0008 (7)	0.0038 (7)	0.0072 (7)
O1W	0.0204 (10)	0.0215 (9)	0.0283 (10)	−0.0019 (8)	−0.0006 (8)	−0.0022 (8)
Cu1	0.0110 (2)	0.0155 (2)	0.00792 (18)	0.000	0.00246 (14)	0.000
Se1	0.01537 (13)	0.02050 (13)	0.01152 (11)	−0.00501 (10)	0.00324 (8)	−0.00052 (9)
P1	0.0146 (3)	0.0151 (3)	0.0144 (3)	0.0005 (2)	0.0040 (2)	0.0027 (2)
B1	0.0247 (17)	0.0276 (16)	0.0271 (16)	−0.0012 (13)	0.0066 (13)	−0.0015 (13)
F4	0.0275 (9)	0.0238 (8)	0.0369 (9)	−0.0034 (7)	0.0066 (7)	0.0056 (7)
F3	0.0413 (11)	0.0443 (11)	0.0420 (10)	−0.0186 (9)	0.0080 (8)	−0.0179 (8)
F1	0.0429 (11)	0.0384 (10)	0.0501 (12)	0.0178 (9)	−0.0167 (9)	−0.0192 (9)
F2	0.0476 (12)	0.0625 (13)	0.0447 (11)	0.0072 (10)	0.0209 (9)	0.0234 (10)

C1—C2	1.496 (3)	C17—H17	0.9500
C1—H1A	0.9800	C18—C19	1.378 (4)
C1—H1B	0.9800	C18—H18	0.9500
C1—H1C	0.9800	C19—C27	1.393 (4)
C2—N1	1.345 (3)	C19—H19	0.9500
C2—C3	1.392 (3)	C20—C26	1.396 (3)
C3—C4	1.410 (3)	C20—P1	1.806 (2)
C3—Se1	1.906 (2)	C21—C28	1.387 (4)
C4—N2	1.349 (3)	C21—C24	1.402 (3)
C4—C5	1.488 (3)	C21—H21	0.9500
C5—H5A	0.9800	C22—C25	1.387 (4)
C5—H5B	0.9800	C22—C23	1.388 (4)
C5—H5C	0.9800	C22—H22	0.9500
C6—C7	1.491 (3)	C23—C24	1.402 (3)
C6—H6A	0.9800	C23—H23	0.9500
C6—H6B	0.9800	C24—P1	1.803 (3)
C6—H6C	0.9800	C25—C28	1.384 (4)
C7—N3	1.351 (3)	C25—H25	0.9500
C7—C8	1.407 (3)	C26—C27	1.389 (4)
C8—C9	1.386 (3)	C26—H26	0.9500
C8—Se1	1.905 (2)	C27—H27	0.9500
C9—N4	1.344 (3)	C28—H28	0.9500
C9—C10	1.491 (3)	N1—N2	1.373 (3)
C10—H10A	0.9800	N1—H1N	0.8800
C10—H10B	0.9800	N2—Cu1	2.0397 (19)
C10—H10C	0.9800	N3—N4	1.366 (3)
C11—C16	1.398 (4)	N3—Cu1i	1.9971 (19)
C11—C12	1.399 (4)	N4—H4N	0.8800
C11—P1	1.804 (2)	O1—Cu1	2.222 (2)
C12—C13	1.393 (4)	O1—H1O	0.8082
C12—H12	0.9500	O2—P1	1.5040 (17)
C13—C14	1.381 (4)	O1W—H1W	0.9003
C13—H13	0.9500	O1W—H2W	0.9489
C14—C15	1.383 (4)	Cu1—N3ii	1.9971 (19)
C14—H14	0.9500	Cu1—N3i	1.9971 (19)
C15—C16	1.391 (4)	Cu1—N2iii	2.0397 (19)
C15—H15	0.9500	B1—F1	1.383 (4)
C16—H16	0.9500	B1—F2	1.387 (4)
C17—C18	1.394 (3)	B1—F3	1.394 (4)
C17—C20	1.395 (3)	B1—F4	1.402 (4)
C2—C1—H1A	109.5	C18—C19—H19	120.2
C2—C1—H1B	109.5	C27—C19—H19	120.2
H1A—C1—H1B	109.5	C17—C20—C26	119.4 (2)
C2—C1—H1C	109.5	C17—C20—P1	121.94 (18)
H1A—C1—H1C	109.5	C26—C20—P1	118.57 (18)
H1B—C1—H1C	109.5	C28—C21—C24	120.0 (2)
N1—C2—C3	106.0 (2)	C28—C21—H21	120.0
N1—C2—C1	122.2 (2)	C24—C21—H21	120.0
C3—C2—C1	131.7 (2)	C25—C22—C23	120.2 (2)
C2—C3—C4	106.5 (2)	C25—C22—H22	119.9
C2—C3—Se1	126.91 (18)	C23—C22—H22	119.9
C4—C3—Se1	126.17 (17)	C22—C23—C24	120.1 (2)
N2—C4—C3	109.6 (2)	C22—C23—H23	120.0
N2—C4—C5	123.7 (2)	C24—C23—H23	120.0
C3—C4—C5	126.7 (2)	C21—C24—C23	119.2 (2)
C4—C5—H5A	109.5	C21—C24—P1	118.74 (19)
C4—C5—H5B	109.5	C23—C24—P1	122.04 (19)
H5A—C5—H5B	109.5	C28—C25—C22	120.2 (3)
C4—C5—H5C	109.5	C28—C25—H25	119.9
H5A—C5—H5C	109.5	C22—C25—H25	119.9
H5B—C5—H5C	109.5	C27—C26—C20	119.9 (2)
C7—C6—H6A	109.5	C27—C26—H26	120.0
C7—C6—H6B	109.5	C20—C26—H26	120.0
H6A—C6—H6B	109.5	C26—C27—C19	120.5 (3)
C7—C6—H6C	109.5	C26—C27—H27	119.8
H6A—C6—H6C	109.5	C19—C27—H27	119.8
H6B—C6—H6C	109.5	C25—C28—C21	120.4 (2)
N3—C7—C8	109.2 (2)	C25—C28—H28	119.8
N3—C7—C6	121.3 (2)	C21—C28—H28	119.8
C8—C7—C6	129.5 (2)	C2—N1—N2	112.47 (19)
C9—C8—C7	106.4 (2)	C2—N1—H1N	123.8
C9—C8—Se1	125.73 (18)	N2—N1—H1N	123.8
C7—C8—Se1	127.30 (18)	C4—N2—N1	105.36 (18)
N4—C9—C8	106.6 (2)	C4—N2—Cu1	130.69 (16)
N4—C9—C10	122.4 (2)	N1—N2—Cu1	122.26 (14)
C8—C9—C10	130.9 (2)	C7—N3—N4	105.99 (18)
C9—C10—H10A	109.5	C7—N3—Cu1i	130.26 (16)
C9—C10—H10B	109.5	N4—N3—Cu1i	122.83 (14)
H10A—C10—H10B	109.5	C9—N4—N3	111.75 (19)
C9—C10—H10C	109.5	C9—N4—H4N	124.1
H10A—C10—H10C	109.5	N3—N4—H4N	124.1
H10B—C10—H10C	109.5	Cu1—O1—H1O	128.2
C16—C11—C12	119.5 (2)	H1W—O1W—H2W	108.7
C16—C11—P1	118.0 (2)	N3ii—Cu1—N3i	158.75 (11)
C12—C11—P1	122.53 (19)	N3ii—Cu1—N2	89.38 (8)
C13—C12—C11	120.0 (3)	N3i—Cu1—N2	90.43 (8)
C13—C12—H12	120.0	N3ii—Cu1—N2iii	90.43 (8)
C11—C12—H12	120.0	N3i—Cu1—N2iii	89.38 (8)
C14—C13—C12	120.2 (3)	N2—Cu1—N2iii	178.95 (11)
C14—C13—H13	119.9	N3ii—Cu1—O1	100.62 (6)
C12—C13—H13	119.9	N3i—Cu1—O1	100.62 (6)
C13—C14—C15	120.2 (3)	N2—Cu1—O1	90.53 (6)
C13—C14—H14	119.9	N2iii—Cu1—O1	90.53 (6)
C15—C14—H14	119.9	C8—Se1—C3	100.52 (10)
C14—C15—C16	120.5 (3)	O2—P1—C24	112.46 (11)
C14—C15—H15	119.7	O2—P1—C11	112.16 (11)
C16—C15—H15	119.7	C24—P1—C11	106.30 (11)
C15—C16—C11	119.7 (3)	O2—P1—C20	111.92 (11)
C15—C16—H16	120.2	C24—P1—C20	106.62 (11)
C11—C16—H16	120.2	C11—P1—C20	106.98 (11)
C18—C17—C20	120.1 (2)	F1—B1—F2	110.3 (2)
C18—C17—H17	119.9	F1—B1—F3	108.6 (3)
C20—C17—H17	119.9	F2—B1—F3	109.7 (3)
C19—C18—C17	120.4 (2)	F1—B1—F4	108.7 (2)
C19—C18—H18	119.8	F2—B1—F4	110.2 (2)
C17—C18—H18	119.8	F3—B1—F4	109.3 (2)
C18—C19—C27	119.7 (2)
N1—C2—C3—C4	0.3 (3)	C3—C4—N2—N1	0.2 (2)
C1—C2—C3—C4	−176.6 (3)	C5—C4—N2—N1	178.7 (2)
N1—C2—C3—Se1	173.45 (17)	C3—C4—N2—Cu1	165.24 (16)
C1—C2—C3—Se1	−3.4 (4)	C5—C4—N2—Cu1	−16.2 (3)
C2—C3—C4—N2	−0.3 (3)	C2—N1—N2—C4	0.0 (3)
Se1—C3—C4—N2	−173.53 (16)	C2—N1—N2—Cu1	−166.62 (16)
C2—C3—C4—C5	−178.8 (2)	C8—C7—N3—N4	−0.5 (2)
Se1—C3—C4—C5	8.0 (3)	C6—C7—N3—N4	177.6 (2)
N3—C7—C8—C9	1.3 (3)	C8—C7—N3—Cu1i	168.54 (16)
C6—C7—C8—C9	−176.6 (2)	C6—C7—N3—Cu1i	−13.4 (3)
N3—C7—C8—Se1	173.23 (16)	C8—C9—N4—N3	1.3 (3)
C6—C7—C8—Se1	−4.7 (4)	C10—C9—N4—N3	−176.2 (2)
C7—C8—C9—N4	−1.6 (3)	C7—N3—N4—C9	−0.5 (2)
Se1—C8—C9—N4	−173.66 (16)	Cu1i—N3—N4—C9	−170.57 (15)
C7—C8—C9—C10	175.6 (2)	C4—N2—Cu1—N3ii	−146.4 (2)
Se1—C8—C9—C10	3.5 (4)	N1—N2—Cu1—N3ii	16.47 (17)
C16—C11—C12—C13	0.0 (4)	C4—N2—Cu1—N3i	54.8 (2)
P1—C11—C12—C13	179.83 (19)	N1—N2—Cu1—N3i	−142.28 (17)
C11—C12—C13—C14	−0.5 (4)	C4—N2—Cu1—O1	−45.8 (2)
C12—C13—C14—C15	0.5 (4)	N1—N2—Cu1—O1	117.09 (17)
C13—C14—C15—C16	−0.1 (4)	C9—C8—Se1—C3	−84.4 (2)
C14—C15—C16—C11	−0.4 (4)	C7—C8—Se1—C3	105.1 (2)
C12—C11—C16—C15	0.4 (4)	C2—C3—Se1—C8	106.5 (2)
P1—C11—C16—C15	−179.4 (2)	C4—C3—Se1—C8	−81.6 (2)
C20—C17—C18—C19	0.4 (4)	C21—C24—P1—O2	−51.1 (2)
C17—C18—C19—C27	0.1 (4)	C23—C24—P1—O2	130.0 (2)
C18—C17—C20—C26	−0.9 (4)	C21—C24—P1—C11	72.0 (2)
C18—C17—C20—P1	175.1 (2)	C23—C24—P1—C11	−106.8 (2)
C25—C22—C23—C24	−0.4 (4)	C21—C24—P1—C20	−174.10 (19)
C28—C21—C24—C23	0.5 (4)	C23—C24—P1—C20	7.0 (2)
C28—C21—C24—P1	−178.4 (2)	C16—C11—P1—O2	−52.4 (2)
C22—C23—C24—C21	0.2 (4)	C12—C11—P1—O2	127.8 (2)
C22—C23—C24—P1	179.02 (19)	C16—C11—P1—C24	−175.71 (19)
C23—C22—C25—C28	0.1 (4)	C12—C11—P1—C24	4.5 (2)
C17—C20—C26—C27	0.9 (4)	C16—C11—P1—C20	70.7 (2)
P1—C20—C26—C27	−175.2 (2)	C12—C11—P1—C20	−109.1 (2)
C20—C26—C27—C19	−0.5 (4)	C17—C20—P1—O2	155.2 (2)
C18—C19—C27—C26	−0.1 (5)	C26—C20—P1—O2	−28.8 (2)
C22—C25—C28—C21	0.6 (4)	C17—C20—P1—C24	−81.5 (2)
C24—C21—C28—C25	−0.9 (4)	C26—C20—P1—C24	94.6 (2)
C3—C2—N1—N2	−0.2 (3)	C17—C20—P1—C11	31.9 (2)
C1—C2—N1—N2	177.0 (2)	C26—C20—P1—C11	−152.0 (2)

D—H···A	D—H	H···A	D···A	D—H···A
O1W—H1W···F2	0.90	2.14	3.002 (3)	161
O1W—H1W···F3	0.90	2.51	3.115 (3)	125
O1W—H2W···O2	0.95	1.90	2.785 (3)	155
O1—H1O···O2	0.81	1.95	2.752 (2)	173
N1—H1N···F4iv	0.88	2.06	2.861 (3)	152
N4—H4N···O1Wv	0.88	1.86	2.730 (3)	170

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O1W—H1W⋯F2	0.90	2.14	3.002 (3)	161
O1W—H1W⋯F3	0.90	2.51	3.115 (3)	125
O1W—H2W⋯O2	0.95	1.90	2.785 (3)	155
O1—H1O⋯O2	0.81	1.95	2.752 (2)	173
N1—H1N⋯F4i	0.88	2.06	2.861 (3)	152
N4—H4N⋯O1Wii	0.88	1.86	2.730 (3)	170

Symmetry codes: (i) ; (ii) .