Aqua­bis(9-hydroxy­fluorene-9-carboxyl­ato)(methanol)copper(II) methanol disolvate

In the title mononuclear complex, [Cu(C₁₄H₉O₃)₂(CH₄O)(H₂O)]·2CH₃OH, the Cu^II atom has an elongated octahedral coordination environment, defined by two hydroxyl and two carboxyl­ate O atoms from two bidentate 9-hydroxy­fluorene-9-carboxyl­ate ligands, and one water and one methanol mol­ecule in cis positions. A supramolecular chain structure is constructed via hydrogen-bonding interactions.

Key indicators

• Single-crystal X-ray study
• T = 293 K
• Mean [sigma](C-C) = 0.006 Å
• R factor = 0.057
• wR factor = 0.154
• Data-to-parameter ratio = 17.1

checkCIF/PLATON results

No syntax errors found



Alert level B
PLAT232_ALERT_2_B Hirshfeld Test Diff (M-X)  Cu1    -   O7      ..      11.54 su

Alert level C
PLAT042_ALERT_1_C Calc. and Rep. MoietyFormula Strings Differ ....          ?
PLAT094_ALERT_2_C Ratio of Maximum / Minimum Residual Density ....       2.26
PLAT220_ALERT_2_C Large Non-Solvent    C     Ueq(max)/Ueq(min) ...       2.75 Ratio
PLAT720_ALERT_4_C Number of Unusual/Non-Standard Label(s) ........          2
PLAT790_ALERT_4_C Centre of Gravity not Within Unit Cell: Resd.  #          3
              C H4 O

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

   1 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
   2 ALERT type 4 Improvement, methodology, query or suggestion

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Computing details

Data collection: RAPID-AUTO (Rigaku Corporation, 1998); cell refinement: RAPID-AUTO; data reduction: CrystalStructure (Rigaku/MSC, 2002); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEPII (Johnson, 1976); software used to prepare material for publication: SHELXL97.

Aquabis(9-hydroxyfluorene-9-carboxylato)(methanol)copper(II) methanol disolvate

Crystal data

[Cu(C14H9O3)2(CH4O)(H2O)]·2CH4O	F(000) = 1308
Mr = 628.12	Dx = 1.397 Mg m^−3
Monoclinic, P21/n	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2yn	Cell parameters from 19670 reflections
a = 13.592 (3) Å	θ = 3.1–27.5°
b = 7.5178 (15) Å	µ = 0.79 mm^−1
c = 29.233 (6) Å	T = 293 K
β = 90.69 (3)°	Prism, blue
V = 2986.9 (11) Å^3	0.39 × 0.25 × 0.18 mm
Z = 4

Data collection

Rigaku RAXIS-RAPID diffractometer	6772 independent reflections
Radiation source: fine-focus sealed tube	5332 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.042
Detector resolution: 10 pixels mm^-1	θmax = 27.5°, θmin = 3.0°
ω scans	h = −17→17
Absorption correction: multi-scan (ABSCOR; Higashi, 1995)	k = −9→9
Tmin = 0.749, Tmax = 0.871	l = −37→37
26886 measured reflections

Refinement

Refinement on F^2	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F^2 > 2σ(F^2)] = 0.057	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.154	H atoms treated by a mixture of independent and constrained refinement
S = 1.05	w = 1/[σ^2(Fo^2) + (0.0755P)^2 + 2.4818P] where P = (Fo^2 + 2Fc^2)/3
6772 reflections	(Δ/σ)max = 0.001
397 parameters	Δρmax = 0.86 e Å^−3
5 restraints	Δρmin = −0.38 e Å^−3

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

	x	y	z	Uiso*/Ueq
Cu1	0.33997 (2)	0.36708 (4)	0.294648 (12)	0.04010 (13)
O1	0.30838 (15)	0.6092 (2)	0.31333 (7)	0.0425 (4)
O2	0.26438 (19)	0.8120 (3)	0.36392 (9)	0.0603 (6)
O3	0.24581 (17)	0.3421 (3)	0.36143 (8)	0.0501 (5)
O4	0.38224 (14)	0.1320 (2)	0.27548 (7)	0.0447 (5)
O5	0.49370 (15)	−0.0818 (3)	0.28452 (8)	0.0507 (5)
O6	0.46237 (14)	0.3505 (2)	0.33194 (8)	0.0440 (5)
O7	0.4432 (2)	0.5437 (4)	0.23990 (9)	0.0683 (7)
O8	0.1881 (4)	1.0749 (4)	0.41502 (13)	0.1229 (16)
O9	0.5614 (2)	−0.3602 (3)	0.34001 (16)	0.0978 (12)
O1W	0.22488 (17)	0.3526 (3)	0.25478 (8)	0.0505 (5)
C1	0.2697 (2)	0.6564 (4)	0.35124 (10)	0.0412 (6)
C2	0.2229 (2)	0.5102 (4)	0.38122 (11)	0.0442 (7)
C3	0.1122 (2)	0.5497 (4)	0.38305 (11)	0.0482 (7)
C4	0.0438 (3)	0.5499 (5)	0.34786 (15)	0.0658 (9)
C5	−0.0525 (3)	0.6008 (6)	0.3577 (2)	0.0854 (14)
C6	−0.0772 (3)	0.6507 (7)	0.4015 (2)	0.0986 (18)
C7	−0.0095 (4)	0.6501 (6)	0.43671 (19)	0.0855 (14)
C8	0.0876 (3)	0.5993 (4)	0.42778 (13)	0.0590 (9)
C9	0.1746 (3)	0.5843 (4)	0.45750 (12)	0.0595 (9)
C10	0.1880 (5)	0.6107 (6)	0.50454 (15)	0.0877 (15)
C11	0.2780 (6)	0.5783 (7)	0.52393 (17)	0.107 (2)
C12	0.3557 (5)	0.5206 (8)	0.49762 (19)	0.0998 (17)
C13	0.3449 (3)	0.4971 (6)	0.45089 (15)	0.0743 (11)
C14	0.2540 (3)	0.5282 (4)	0.43105 (11)	0.0517 (7)
C15	0.46198 (19)	0.0683 (4)	0.29290 (10)	0.0389 (6)
C16	0.5199 (2)	0.1905 (4)	0.32610 (10)	0.0404 (6)
C17	0.6235 (2)	0.2261 (4)	0.30864 (11)	0.0437 (6)
C18	0.6516 (2)	0.3083 (4)	0.26848 (12)	0.0540 (8)
C19	0.7516 (3)	0.3278 (5)	0.26036 (15)	0.0666 (10)
C20	0.8211 (3)	0.2676 (6)	0.29128 (16)	0.0738 (12)
C21	0.7936 (3)	0.1855 (6)	0.33135 (16)	0.0691 (11)
C22	0.6933 (2)	0.1656 (4)	0.34054 (12)	0.0505 (7)
C23	0.6417 (3)	0.0875 (4)	0.37984 (12)	0.0530 (8)
C24	0.6770 (3)	0.0088 (6)	0.41966 (15)	0.0764 (12)
C25	0.6098 (5)	−0.0624 (7)	0.45021 (16)	0.0909 (15)
C26	0.5102 (4)	−0.0556 (6)	0.44143 (14)	0.0812 (13)
C27	0.4737 (3)	0.0271 (5)	0.40202 (12)	0.0631 (9)
C28	0.5404 (2)	0.0983 (4)	0.37152 (11)	0.0464 (7)
C29	0.4253 (4)	0.5391 (7)	0.19310 (15)	0.0831 (12)
C30	0.1517 (8)	1.0766 (8)	0.4546 (3)	0.191 (5)
C31	0.6559 (4)	−0.3570 (6)	0.3522 (2)	0.1076 (19)
H1W1	0.198 (3)	0.448 (3)	0.2459 (11)	0.076*
H1W2	0.223 (3)	0.274 (3)	0.2342 (9)	0.076*
H4	0.0613	0.5172	0.3184	0.079*
H5	−0.1002	0.6011	0.3346	0.103*
H6	−0.1415	0.6856	0.4073	0.118*
H7	−0.0277	0.6830	0.4661	0.103*
H10	0.1362	0.6499	0.5224	0.105*
H11	0.2872	0.5952	0.5552	0.128*
H12	0.4162	0.4973	0.5116	0.120*
H13	0.3978	0.4611	0.4333	0.089*
H18	0.6049	0.3494	0.2475	0.065*
H19	0.7719	0.3825	0.2335	0.080*
H20	0.8875	0.2826	0.2851	0.089*
H21	0.8410	0.1439	0.3519	0.083*
H24	0.7442	0.0036	0.4258	0.092*
H25	0.6327	−0.1154	0.4770	0.109*
H26	0.4668	−0.1066	0.4620	0.097*
H27	0.4064	0.0342	0.3963	0.076*
H29A	0.3679	0.6087	0.1860	0.125*
H29B	0.4147	0.4184	0.1836	0.125*
H29C	0.4809	0.5871	0.1774	0.125*
H30A	0.1982	1.0274	0.4761	0.287*
H30B	0.0925	1.0068	0.4547	0.287*
H30C	0.1367	1.1968	0.4631	0.287*
H31A	0.6888	−0.2638	0.3360	0.161*
H31B	0.6857	−0.4692	0.3451	0.161*
H31C	0.6616	−0.3356	0.3845	0.161*
H32	0.230 (3)	0.259 (4)	0.3795 (11)	0.075*
H33	0.497 (2)	0.443 (3)	0.3345 (13)	0.066*
H34	0.4384	0.6463	0.2491	0.102*
H35	0.2113	0.9763	0.4098	0.184*
H36	0.5521	−0.2917	0.3186	0.147*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
Cu1	0.03667 (19)	0.03185 (19)	0.0519 (2)	0.00543 (13)	0.00491 (14)	−0.00101 (15)
O1	0.0465 (11)	0.0323 (9)	0.0490 (11)	0.0025 (8)	0.0110 (9)	0.0033 (8)
O2	0.0758 (16)	0.0328 (10)	0.0729 (15)	−0.0033 (10)	0.0265 (13)	−0.0056 (10)
O3	0.0610 (13)	0.0309 (10)	0.0590 (13)	−0.0009 (9)	0.0212 (11)	−0.0002 (9)
O4	0.0392 (10)	0.0352 (10)	0.0598 (12)	0.0044 (8)	−0.0035 (9)	−0.0035 (9)
O5	0.0462 (11)	0.0338 (10)	0.0720 (14)	0.0076 (9)	−0.0023 (10)	−0.0077 (10)
O6	0.0391 (10)	0.0297 (9)	0.0633 (13)	0.0029 (8)	0.0038 (9)	−0.0069 (9)
O7	0.0686 (16)	0.0606 (15)	0.0761 (17)	0.0058 (13)	0.0135 (13)	0.0044 (13)
O8	0.221 (5)	0.0401 (14)	0.110 (3)	0.006 (2)	0.097 (3)	0.0012 (16)
O9	0.080 (2)	0.0398 (14)	0.172 (4)	0.0002 (13)	−0.039 (2)	0.0067 (17)
O1W	0.0514 (12)	0.0364 (11)	0.0634 (14)	0.0120 (9)	−0.0090 (10)	−0.0080 (10)
C1	0.0393 (14)	0.0334 (13)	0.0511 (16)	−0.0005 (11)	0.0077 (12)	−0.0010 (12)
C2	0.0476 (16)	0.0313 (13)	0.0539 (17)	−0.0004 (12)	0.0134 (13)	−0.0023 (12)
C3	0.0478 (16)	0.0351 (14)	0.0621 (19)	−0.0040 (12)	0.0134 (14)	−0.0008 (14)
C4	0.055 (2)	0.056 (2)	0.087 (3)	−0.0087 (16)	0.0066 (18)	−0.0019 (19)
C5	0.050 (2)	0.069 (3)	0.137 (4)	−0.0045 (19)	−0.004 (2)	0.008 (3)
C6	0.050 (2)	0.084 (3)	0.163 (6)	0.006 (2)	0.034 (3)	0.000 (3)
C7	0.074 (3)	0.075 (3)	0.108 (4)	0.002 (2)	0.050 (3)	−0.009 (3)
C8	0.062 (2)	0.0419 (16)	0.073 (2)	−0.0016 (15)	0.0304 (17)	0.0016 (16)
C9	0.086 (3)	0.0406 (16)	0.0523 (18)	−0.0099 (17)	0.0203 (18)	−0.0016 (14)
C10	0.148 (5)	0.057 (2)	0.059 (2)	−0.004 (3)	0.030 (3)	−0.0030 (19)
C11	0.185 (7)	0.075 (3)	0.059 (3)	−0.026 (4)	−0.020 (4)	0.008 (2)
C12	0.122 (4)	0.090 (4)	0.086 (3)	−0.017 (3)	−0.035 (3)	0.014 (3)
C13	0.076 (3)	0.072 (3)	0.074 (3)	−0.005 (2)	−0.012 (2)	0.011 (2)
C14	0.065 (2)	0.0370 (15)	0.0535 (18)	−0.0058 (14)	0.0080 (15)	0.0030 (13)
C15	0.0330 (13)	0.0331 (13)	0.0508 (16)	−0.0008 (10)	0.0075 (11)	−0.0001 (12)
C16	0.0348 (13)	0.0329 (13)	0.0536 (16)	0.0033 (10)	0.0057 (12)	−0.0004 (12)
C17	0.0356 (14)	0.0315 (13)	0.0642 (18)	0.0007 (11)	0.0061 (13)	−0.0049 (13)
C18	0.0500 (17)	0.0444 (16)	0.068 (2)	0.0022 (14)	0.0127 (15)	0.0034 (15)
C19	0.058 (2)	0.0525 (19)	0.090 (3)	−0.0034 (16)	0.028 (2)	0.0016 (19)
C20	0.0435 (19)	0.065 (2)	0.113 (3)	−0.0071 (17)	0.021 (2)	−0.012 (2)
C21	0.0408 (17)	0.067 (2)	0.099 (3)	0.0049 (16)	−0.0058 (19)	−0.013 (2)
C22	0.0400 (15)	0.0402 (15)	0.071 (2)	0.0036 (12)	−0.0010 (14)	−0.0083 (15)
C23	0.0580 (19)	0.0413 (15)	0.0595 (19)	0.0066 (14)	−0.0090 (15)	−0.0048 (15)
C24	0.083 (3)	0.074 (3)	0.072 (3)	0.016 (2)	−0.019 (2)	−0.002 (2)
C25	0.139 (5)	0.074 (3)	0.060 (2)	0.016 (3)	−0.008 (3)	0.011 (2)
C26	0.118 (4)	0.068 (3)	0.059 (2)	−0.006 (3)	0.018 (2)	0.009 (2)
C27	0.076 (2)	0.056 (2)	0.058 (2)	−0.0057 (18)	0.0140 (18)	−0.0012 (17)
C28	0.0531 (17)	0.0327 (14)	0.0536 (17)	0.0000 (12)	0.0050 (14)	−0.0030 (12)
C29	0.088 (3)	0.084 (3)	0.077 (3)	0.002 (2)	0.007 (2)	0.004 (2)
C30	0.365 (13)	0.064 (3)	0.148 (6)	−0.023 (5)	0.139 (8)	−0.012 (4)
C31	0.120 (5)	0.061 (3)	0.142 (5)	−0.005 (3)	−0.028 (4)	−0.016 (3)

Geometric parameters (Å, º)

Cu1—O1	1.950 (2)	C11—C12	1.384 (9)
Cu1—O3	2.355 (2)	C11—H11	0.9300
Cu1—O4	1.943 (2)	C12—C13	1.384 (7)
Cu1—O6	1.982 (2)	C12—H12	0.9300
Cu1—O7	2.519 (2)	C13—C14	1.378 (5)
Cu1—O1W	1.943 (2)	C13—H13	0.9300
O1—C1	1.283 (4)	C15—C16	1.545 (4)
O2—C1	1.229 (3)	C16—C28	1.521 (4)
O4—C15	1.284 (3)	C16—C17	1.527 (4)
O5—C15	1.233 (3)	C17—C18	1.384 (5)
O3—C2	1.426 (3)	C17—C22	1.398 (4)
O3—H32	0.85 (3)	C18—C19	1.391 (5)
O6—C16	1.446 (3)	C18—H18	0.9300
O6—H33	0.84 (3)	C19—C20	1.376 (6)
O7—C29	1.387 (5)	C19—H19	0.9300
O7—H34	0.8200	C20—C21	1.380 (6)
O8—C30	1.264 (7)	C20—H20	0.9300
O8—H35	0.8200	C21—C22	1.401 (5)
O9—C31	1.330 (6)	C21—H21	0.9300
O9—H36	0.8200	C22—C23	1.475 (5)
O1W—H1W1	0.84 (3)	C23—C24	1.386 (5)
O1W—H1W2	0.84 (3)	C23—C28	1.398 (5)
C1—C2	1.547 (4)	C24—C25	1.392 (7)
C2—C14	1.518 (5)	C24—H24	0.9300
C2—C3	1.536 (4)	C25—C26	1.376 (7)
C3—C4	1.378 (5)	C25—H25	0.9300
C3—C8	1.404 (5)	C26—C27	1.395 (6)
C4—C5	1.397 (6)	C26—H26	0.9300
C4—H4	0.9300	C27—C28	1.387 (5)
C5—C6	1.380 (8)	C27—H27	0.9300
C5—H5	0.9300	C29—H29A	0.9600
C6—C7	1.373 (8)	C29—H29B	0.9600
C6—H6	0.9300	C29—H29C	0.9600
C7—C8	1.400 (5)	C30—H30A	0.9600
C7—H7	0.9300	C30—H30B	0.9600
C8—C9	1.464 (6)	C30—H30C	0.9600
C9—C10	1.399 (6)	C31—H31A	0.9600
C9—C14	1.400 (5)	C31—H31B	0.9600
C10—C11	1.364 (8)	C31—H31C	0.9600
C10—H10	0.9300
O1—Cu1—O3	73.65 (8)	C11—C10—H10	120.4
O1—Cu1—O6	95.20 (8)	C11—C12—H12	119.5
O1—Cu1—O7	79.20 (8)	C12—C11—H11	119.6
O3—Cu1—O7	151.78 (9)	C12—C13—H13	120.7
O4—Cu1—O1	175.43 (8)	C13—C12—C11	121.1 (5)
O4—Cu1—O3	109.39 (8)	C13—C12—H12	119.5
O4—Cu1—O6	81.51 (8)	C13—C14—C2	128.8 (3)
O4—Cu1—O7	97.31 (9)	C13—C14—C9	120.8 (4)
O4—Cu1—O1W	90.84 (8)	C14—C2—C1	111.6 (2)
O6—Cu1—O3	89.99 (9)	C14—C2—C3	102.2 (2)
O6—Cu1—O7	84.97 (9)	C14—C9—C8	108.6 (3)
O1W—Cu1—O1	92.41 (9)	C14—C13—C12	118.6 (5)
O1W—Cu1—O3	92.93 (10)	C14—C13—H13	120.7
O1W—Cu1—O6	172.34 (8)	C15—O4—Cu1	118.41 (18)
O1W—Cu1—O7	95.68 (10)	C16—O6—Cu1	116.01 (17)
Cu1—O3—H32	136 (3)	C16—O6—H33	113 (3)
Cu1—O6—H33	118 (3)	C17—C16—C15	111.0 (2)
Cu1—O1W—H1W1	119 (2)	C17—C18—C19	118.2 (3)
Cu1—O1W—H1W2	119 (2)	C17—C18—H18	120.9
O1—C1—C2	117.9 (2)	C17—C22—C21	119.5 (3)
O2—C1—O1	123.3 (3)	C17—C22—C23	108.9 (3)
O2—C1—C2	118.7 (3)	C18—C17—C16	128.8 (3)
O3—C2—C1	107.9 (2)	C18—C17—C22	121.3 (3)
O3—C2—C3	113.8 (2)	C18—C19—H19	119.4
O3—C2—C14	114.1 (3)	C19—C18—H18	120.9
O4—C15—C16	116.6 (2)	C19—C20—C21	121.0 (3)
O5—C15—O4	123.9 (3)	C19—C20—H20	119.5
O5—C15—C16	119.5 (2)	C20—C19—C18	121.2 (4)
O6—C16—C15	107.3 (2)	C20—C19—H19	119.4
O6—C16—C17	113.3 (2)	C20—C21—C22	119.0 (4)
O6—C16—C28	111.7 (2)	C20—C21—H21	120.5
O7—C29—H29A	109.5	C21—C20—H20	119.5
O7—C29—H29B	109.5	C21—C22—C23	131.6 (3)
O7—C29—H29C	109.5	C22—C17—C16	109.9 (3)
O8—C30—H30A	109.5	C22—C21—H21	120.5
O8—C30—H30B	109.5	C23—C24—C25	118.6 (4)
O8—C30—H30C	109.5	C23—C24—H24	120.7
O9—C31—H31A	109.5	C23—C28—C16	110.4 (3)
O9—C31—H31B	109.5	C24—C23—C22	131.4 (4)
O9—C31—H31C	109.5	C24—C23—C28	120.1 (4)
C1—O1—Cu1	126.46 (18)	C24—C25—H25	119.4
C2—O3—Cu1	112.89 (16)	C25—C24—H24	120.7
C2—O3—H32	110 (3)	C25—C26—C27	120.6 (4)
C3—C2—C1	107.0 (2)	C25—C26—H26	119.7
C3—C4—C5	118.2 (4)	C26—C25—C24	121.2 (4)
C3—C4—H4	120.9	C26—C25—H25	119.4
C3—C8—C9	109.4 (3)	C26—C27—H27	120.8
C4—C3—C2	128.8 (3)	C27—C26—H26	119.7
C4—C3—C8	121.9 (3)	C27—C28—C16	128.5 (3)
C4—C5—H5	119.9	C27—C28—C23	121.1 (3)
C5—C4—H4	120.9	C28—C16—C15	111.4 (2)
C5—C6—C7	121.8 (4)	C28—C16—C17	102.2 (2)
C5—C6—H6	119.1	C28—C27—C26	118.3 (4)
C6—C5—C4	120.3 (5)	C28—C27—H27	120.8
C6—C5—H5	119.9	C28—C23—C22	108.5 (3)
C6—C7—C8	119.1 (4)	C29—O7—H34	109.5
C6—C7—H7	120.5	C30—O8—H35	109.5
C7—C6—H6	119.1	C31—O9—H36	109.5
C7—C8—C3	118.8 (4)	H1W1—O1W—H1W2	111.4 (17)
C7—C8—C9	131.8 (4)	H29A—C29—H29B	109.5
C8—C3—C2	109.2 (3)	H29A—C29—H29C	109.5
C8—C7—H7	120.5	H29B—C29—H29C	109.5
C9—C10—H10	120.4	H30A—C30—H30B	109.5
C9—C14—C2	110.4 (3)	H30A—C30—H30C	109.5
C10—C9—C8	131.9 (4)	H30B—C30—H30C	109.5
C10—C9—C14	119.5 (4)	H31A—C31—H31B	109.5
C10—C11—C12	120.8 (5)	H31A—C31—H31C	109.5
C10—C11—H11	119.6	H31B—C31—H31C	109.5
C11—C10—C9	119.3 (5)
Cu1—O1—C1—O2	169.2 (2)	C4—C3—C8—C9	179.5 (3)
Cu1—O1—C1—C2	−13.9 (4)	C4—C5—C6—C7	−0.8 (7)
Cu1—O3—C2—C1	−0.3 (3)	C5—C6—C7—C8	0.7 (7)
Cu1—O3—C2—C3	118.3 (2)	C6—C7—C8—C3	−0.3 (6)
Cu1—O3—C2—C14	−125.0 (2)	C6—C7—C8—C9	−179.5 (4)
Cu1—O4—C15—O5	177.2 (2)	C7—C8—C9—C10	2.2 (7)
Cu1—O4—C15—C16	−2.9 (3)	C7—C8—C9—C14	−179.7 (4)
Cu1—O6—C16—C15	−3.7 (3)	C8—C3—C4—C5	−0.2 (5)
Cu1—O6—C16—C17	119.2 (2)	C8—C9—C10—C11	176.8 (4)
Cu1—O6—C16—C28	−126.0 (2)	C8—C9—C14—C2	2.2 (4)
O1—Cu1—O3—C2	−4.29 (19)	C8—C9—C14—C13	−177.7 (3)
O1—Cu1—O6—C16	−174.77 (18)	C9—C10—C11—C12	0.3 (7)
O1—C1—C2—O3	7.7 (4)	C10—C9—C14—C2	−179.4 (3)
O1—C1—C2—C3	−115.2 (3)	C10—C9—C14—C13	0.7 (5)
O1—C1—C2—C14	133.8 (3)	C10—C11—C12—C13	1.1 (8)
O2—C1—C2—O3	−175.2 (3)	C11—C12—C13—C14	−1.6 (7)
O2—C1—C2—C3	61.9 (4)	C12—C13—C14—C2	−179.2 (4)
O2—C1—C2—C14	−49.1 (4)	C12—C13—C14—C9	0.7 (6)
O3—Cu1—O1—C1	10.1 (2)	C14—C2—C3—C4	−178.8 (3)
O3—Cu1—O4—C15	−86.4 (2)	C14—C2—C3—C8	4.8 (3)
O3—Cu1—O6—C16	111.65 (18)	C14—C9—C10—C11	−1.1 (6)
O3—C2—C3—C4	−55.2 (4)	C15—C16—C17—C18	61.4 (4)
O3—C2—C3—C8	128.4 (3)	C15—C16—C17—C22	−120.1 (3)
O3—C2—C14—C9	−127.6 (3)	C15—C16—C28—C23	120.3 (3)
O3—C2—C14—C13	52.3 (4)	C15—C16—C28—C27	−58.1 (4)
O4—Cu1—O3—C2	172.13 (19)	C16—C17—C18—C19	179.1 (3)
O4—Cu1—O6—C16	2.04 (18)	C16—C17—C22—C21	−179.9 (3)
O4—C15—C16—O6	4.2 (3)	C16—C17—C22—C23	0.3 (3)
O4—C15—C16—C17	−120.1 (3)	C17—C16—C28—C23	1.7 (3)
O4—C15—C16—C28	126.7 (3)	C17—C16—C28—C27	−176.7 (3)
O5—C15—C16—O6	−175.9 (2)	C17—C18—C19—C20	−0.1 (5)
O5—C15—C16—C17	59.8 (3)	C17—C22—C23—C24	179.3 (4)
O5—C15—C16—C28	−53.4 (3)	C17—C22—C23—C28	0.8 (4)
O6—Cu1—O1—C1	−78.4 (2)	C18—C17—C22—C21	−1.2 (5)
O6—Cu1—O3—C2	91.1 (2)	C18—C17—C22—C23	179.0 (3)
O6—Cu1—O4—C15	0.6 (2)	C18—C19—C20—C21	0.2 (6)
O6—C16—C17—C18	−59.4 (4)	C19—C20—C21—C22	−0.7 (6)
O6—C16—C17—C22	119.1 (3)	C20—C21—C22—C17	1.2 (5)
O6—C16—C28—C23	−119.7 (3)	C20—C21—C22—C23	−179.1 (4)
O6—C16—C28—C27	61.8 (4)	C21—C22—C23—C24	−0.4 (6)
O1W—Cu1—O1—C1	102.4 (2)	C21—C22—C23—C28	−178.9 (4)
O1W—Cu1—O3—C2	−95.9 (2)	C22—C17—C18—C19	0.6 (5)
O1W—Cu1—O4—C15	−179.8 (2)	C22—C23—C24—C25	−176.8 (4)
C1—C2—C3—C4	63.8 (4)	C22—C23—C28—C16	−1.6 (3)
C1—C2—C3—C8	−112.6 (3)	C22—C23—C28—C27	177.0 (3)
C1—C2—C14—C9	109.8 (3)	C23—C24—C25—C26	0.0 (7)
C1—C2—C14—C13	−70.3 (4)	C24—C23—C28—C16	179.7 (3)
C2—C3—C4—C5	−176.3 (3)	C24—C23—C28—C27	−1.8 (5)
C2—C3—C8—C9	−3.8 (3)	C24—C25—C26—C27	−1.6 (7)
C2—C3—C8—C7	176.8 (3)	C25—C26—C27—C28	1.5 (6)
C3—C2—C14—C9	−4.2 (3)	C26—C27—C28—C16	178.5 (3)
C3—C2—C14—C13	175.7 (3)	C26—C27—C28—C23	0.2 (5)
C3—C4—C5—C6	0.6 (6)	C28—C16—C17—C18	−179.8 (3)
C3—C8—C9—C10	−177.1 (4)	C28—C16—C17—C22	−1.2 (3)
C3—C8—C9—C14	1.1 (4)	C28—C23—C24—C25	1.6 (6)
C4—C3—C8—C7	0.1 (5)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
O3—H32···O8^i	0.85 (3)	1.83 (3)	2.671 (4)	176 (4)
O6—H33···O9^ii	0.84 (3)	1.73 (3)	2.567 (3)	176 (4)
O7—H34···O5^ii	0.82	2.41	3.175 (4)	156
O8—H35···O2	0.82	1.97	2.693 (4)	147
O9—H36···O5	0.82	2.02	2.797 (4)	157
O1W—H1W2···O1^iii	0.84 (3)	1.91 (3)	2.737 (3)	169 (4)
O1W—H1W1···O4^iv	0.84 (3)	1.87 (3)	2.699 (3)	170 (4)

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