A fourfold inter­penetrating diamond-like three-dimensional zinc(II) coordination polymer: synthesis, crystal structure and physical properties

Excellent fluorescence properties are exhibited by d¹⁰ metal compounds. The novel three-dimensional Zn^II coordination framework, poly[[{μ₂-bis­[4-(2-methyl-1H-imidazol-1-yl)phen­yl] ether-κ²N³:N^3′}(μ₂-furan-2,5-di­carboxyl­ato-κ²O²:O⁵)zinc(II)] 1.76-hydrate], {[Zn(C₆H₂O₅)(C₂₀H₁₈N₄O)]·1.76H₂O}_n, has been pre­pared and characterized using IR spectroscopy, elemental analysis and single-crystal X-ray diffraction. The crystal structure analysis revealed that the compound exhibits a novel fourfold inter­penetrating diamond-like network. This polymer also displays a strong fluorescence emission in the solid state at room temperature.

Computing details

Data collection: APEX3 (Bruker, 2016); cell refinement: SAINT (Bruker, 2016); data reduction: SAINT (Bruker, 2016); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL2014 (Sheldrick, 2015); molecular graphics: DIAMOND (Brandenburg & Putz, 2005); software used to prepare material for publication: SHELXL2014 (Sheldrick, 2015).

Poly[[{µ₂-bis[4-(2-methyl-1H-imidazol-1-yl)phenyl] ether-κ²N³:N^3'}(µ₂-furan-2,5-dicarboxylato-κ²O²:O⁵)zinc(II)] 1.76-hydrate]

Crystal data

[Zn(C6H2O5)(C20H18N4O)]·1.76H2O	F(000) = 1198
Mr = 581.56	Dx = 1.443 Mg m^−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
a = 11.622 (5) Å	Cell parameters from 9602 reflections
b = 12.346 (6) Å	θ = 2.9–27.4°
c = 18.669 (9) Å	µ = 0.97 mm^−1
β = 92.13 (3)°	T = 293 K
V = 2677 (2) Å^3	Block, colorless
Z = 4	0.21 × 0.20 × 0.19 mm

Data collection

Bruker APEXII CCD diffractometer	4694 reflections with I > 2σ(I)
φ and ω scans	Rint = 0.030
Absorption correction: multi-scan (SADABS; Bruker, 2008)	θmax = 26.0°, θmin = 2.8°
Tmin = 0.815, Tmax = 0.831	h = −14→14
75815 measured reflections	k = −15→15
5259 independent reflections	l = −23→23

Refinement

Refinement on F^2	0 restraints
Least-squares matrix: full	Hydrogen site location: mixed
R[F^2 > 2σ(F^2)] = 0.029	H-atom parameters constrained
wR(F^2) = 0.079	w = 1/[σ^2(Fo^2) + (0.0432P)^2 + 1.3019P] where P = (Fo^2 + 2Fc^2)/3
S = 1.05	(Δ/σ)max = 0.002
5259 reflections	Δρmax = 0.49 e Å^−3
354 parameters	Δρmin = −0.36 e Å^−3

Special details

Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes.

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

	x	y	z	Uiso*/Ueq	Occ. (<1)
C1	0.5367 (2)	0.43499 (18)	0.18771 (16)	0.0573 (6)
H1A	0.5066	0.4148	0.2330	0.086*
H1B	0.6126	0.4056	0.1839	0.086*
H1C	0.4874	0.4071	0.1496	0.086*
C2	0.54176 (15)	0.55437 (16)	0.18253 (10)	0.0327 (4)
C3	0.50141 (17)	0.72303 (15)	0.15807 (11)	0.0385 (4)
H3	0.4623	0.7843	0.1414	0.046*
C4	0.60567 (18)	0.72289 (16)	0.19173 (12)	0.0429 (5)
H4	0.6518	0.7828	0.2021	0.051*
C5	0.73578 (15)	0.57888 (15)	0.24232 (10)	0.0336 (4)
C6	0.73480 (16)	0.52289 (17)	0.30642 (11)	0.0401 (4)
H6	0.6653	0.5089	0.3278	0.048*
C7	0.83724 (17)	0.48756 (17)	0.33894 (10)	0.0401 (4)
H7	0.8370	0.4498	0.3820	0.048*
C8	0.93949 (16)	0.50927 (16)	0.30648 (10)	0.0362 (4)
C9	0.94087 (16)	0.56777 (16)	0.24316 (10)	0.0360 (4)
H9	1.0104	0.5838	0.2225	0.043*
C10	0.83870 (16)	0.60197 (15)	0.21097 (10)	0.0348 (4)
H10	0.8390	0.6406	0.1682	0.042*
C11	1.06815 (17)	0.41327 (17)	0.39102 (12)	0.0422 (5)
C12	1.01238 (17)	0.31617 (17)	0.39990 (11)	0.0435 (5)
H12	0.9527	0.2953	0.3683	0.052*
C13	1.04657 (17)	0.24982 (16)	0.45686 (11)	0.0406 (4)
H13	1.0087	0.1846	0.4642	0.049*
C14	1.13636 (16)	0.28044 (15)	0.50243 (10)	0.0351 (4)
C15	1.19299 (19)	0.37706 (19)	0.49313 (13)	0.0505 (6)
H15	1.2540	0.3969	0.5240	0.061*
C16	1.1576 (2)	0.4444 (2)	0.43701 (14)	0.0562 (6)
H16	1.1942	0.5104	0.4304	0.067*
C17	1.3120 (2)	0.1004 (2)	0.49227 (12)	0.0553 (6)
H17A	1.3663	0.0438	0.5036	0.083*
H17B	1.3525	0.1641	0.4777	0.083*
H17C	1.2604	0.0772	0.4540	0.083*
C18	1.24530 (16)	0.12550 (15)	0.55636 (10)	0.0325 (4)
C19	1.18000 (18)	0.12671 (16)	0.66359 (10)	0.0383 (4)
H19	1.1676	0.1077	0.7109	0.046*
C20	1.13161 (19)	0.21130 (17)	0.62874 (11)	0.0438 (5)
H20	1.0805	0.2611	0.6472	0.053*
C21	0.25083 (15)	0.63055 (16)	0.26829 (9)	0.0325 (4)
C22	0.21898 (15)	0.70943 (15)	0.32380 (9)	0.0301 (4)
C23	0.15612 (19)	0.80050 (17)	0.32017 (10)	0.0421 (5)
H23	0.1187	0.8291	0.2795	0.051*
C24	0.1578 (2)	0.84465 (17)	0.39009 (10)	0.0433 (5)
H24	0.1217	0.9078	0.4045	0.052*
C25	0.22218 (16)	0.77716 (15)	0.43180 (9)	0.0314 (4)
C26	0.25729 (16)	0.78125 (16)	0.50914 (10)	0.0362 (4)
N1	0.46154 (12)	0.61806 (12)	0.15208 (8)	0.0309 (3)
N2	0.63084 (13)	0.61590 (13)	0.20782 (9)	0.0346 (3)
N3	1.17226 (13)	0.20987 (12)	0.56069 (8)	0.0344 (3)
N4	1.25081 (13)	0.07256 (12)	0.61824 (8)	0.0305 (3)
O1	1.04794 (12)	0.48206 (15)	0.33317 (9)	0.0612 (5)
O2	0.21115 (11)	0.65552 (11)	0.20532 (6)	0.0371 (3)
O3	0.31001 (13)	0.55100 (13)	0.28280 (7)	0.0475 (4)
O4	0.26064 (11)	0.69279 (10)	0.39230 (6)	0.0327 (3)
O5	0.22551 (12)	0.86727 (11)	0.53981 (7)	0.0407 (3)
O6	0.30911 (17)	0.70551 (15)	0.53787 (8)	0.0664 (5)
O7	0.47612 (19)	0.48887 (19)	0.38610 (12)	0.0777 (6)	0.91
H7B	0.4251	0.5106	0.3556	0.116*	0.91
H7A	0.4892	0.5392	0.4164	0.116*	0.91
O8	0.5279 (2)	0.6499 (2)	0.48896 (14)	0.0891 (8)	0.85
H8B	0.4615	0.6764	0.4952	0.134*	0.85
H8A	0.5423	0.6046	0.5224	0.134*	0.85
Zn1	0.29611 (2)	0.58356 (2)	0.13066 (2)	0.02567 (8)

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
C1	0.0403 (12)	0.0394 (12)	0.0909 (19)	−0.0002 (9)	−0.0160 (12)	0.0120 (12)
C2	0.0261 (9)	0.0365 (10)	0.0351 (9)	−0.0006 (7)	−0.0009 (7)	0.0044 (8)
C3	0.0377 (10)	0.0315 (9)	0.0454 (11)	0.0029 (8)	−0.0113 (8)	0.0025 (8)
C4	0.0396 (11)	0.0336 (10)	0.0543 (12)	−0.0021 (8)	−0.0132 (9)	0.0009 (9)
C5	0.0277 (9)	0.0366 (10)	0.0358 (10)	0.0022 (7)	−0.0070 (7)	0.0031 (8)
C6	0.0304 (9)	0.0508 (12)	0.0393 (10)	0.0034 (8)	0.0033 (8)	0.0078 (9)
C7	0.0373 (10)	0.0491 (12)	0.0337 (10)	0.0042 (9)	−0.0002 (8)	0.0140 (8)
C8	0.0293 (9)	0.0397 (10)	0.0391 (10)	0.0031 (8)	−0.0070 (8)	0.0086 (8)
C9	0.0274 (9)	0.0423 (11)	0.0379 (10)	−0.0021 (8)	−0.0025 (8)	0.0075 (8)
C10	0.0336 (9)	0.0398 (10)	0.0306 (9)	−0.0024 (8)	−0.0049 (8)	0.0077 (8)
C11	0.0303 (10)	0.0509 (12)	0.0451 (11)	0.0066 (8)	−0.0028 (8)	0.0203 (9)
C12	0.0359 (10)	0.0491 (12)	0.0445 (11)	0.0037 (9)	−0.0103 (9)	0.0067 (9)
C13	0.0400 (10)	0.0344 (10)	0.0471 (11)	0.0013 (8)	−0.0035 (9)	0.0065 (9)
C14	0.0349 (9)	0.0358 (10)	0.0344 (9)	0.0063 (8)	−0.0016 (8)	0.0084 (8)
C15	0.0433 (12)	0.0507 (12)	0.0559 (13)	−0.0089 (10)	−0.0182 (10)	0.0191 (11)
C16	0.0458 (12)	0.0509 (13)	0.0704 (16)	−0.0123 (10)	−0.0160 (11)	0.0313 (12)
C17	0.0744 (16)	0.0523 (13)	0.0406 (12)	0.0179 (12)	0.0209 (11)	0.0144 (10)
C18	0.0357 (9)	0.0312 (9)	0.0306 (9)	0.0024 (8)	0.0011 (7)	0.0044 (7)
C19	0.0512 (12)	0.0373 (10)	0.0269 (9)	0.0037 (9)	0.0059 (8)	0.0003 (8)
C20	0.0526 (12)	0.0406 (11)	0.0390 (11)	0.0129 (9)	0.0118 (9)	0.0029 (8)
C21	0.0295 (9)	0.0420 (10)	0.0260 (9)	−0.0048 (8)	0.0014 (7)	−0.0059 (8)
C22	0.0338 (9)	0.0375 (9)	0.0188 (8)	−0.0046 (7)	0.0000 (7)	−0.0017 (7)
C23	0.0557 (12)	0.0478 (11)	0.0224 (9)	0.0114 (10)	−0.0062 (8)	−0.0002 (8)
C24	0.0605 (13)	0.0410 (11)	0.0280 (9)	0.0148 (10)	−0.0027 (9)	−0.0055 (8)
C25	0.0374 (9)	0.0332 (9)	0.0237 (8)	−0.0009 (7)	0.0018 (7)	−0.0054 (7)
C26	0.0377 (10)	0.0450 (11)	0.0257 (9)	0.0010 (8)	−0.0036 (7)	−0.0043 (8)
N1	0.0262 (7)	0.0334 (8)	0.0327 (8)	0.0005 (6)	−0.0038 (6)	0.0028 (6)
N2	0.0275 (8)	0.0380 (8)	0.0378 (8)	0.0014 (6)	−0.0063 (6)	0.0049 (7)
N3	0.0371 (8)	0.0332 (8)	0.0326 (8)	0.0048 (7)	−0.0006 (6)	0.0065 (6)
N4	0.0367 (8)	0.0302 (8)	0.0243 (7)	0.0030 (6)	−0.0013 (6)	0.0023 (6)
O1	0.0295 (7)	0.0845 (12)	0.0689 (11)	0.0006 (7)	−0.0083 (7)	0.0483 (9)
O2	0.0339 (7)	0.0555 (8)	0.0219 (6)	0.0031 (6)	−0.0004 (5)	−0.0089 (6)
O3	0.0580 (9)	0.0498 (8)	0.0345 (7)	0.0137 (7)	−0.0005 (6)	−0.0075 (6)
O4	0.0399 (7)	0.0361 (7)	0.0219 (6)	0.0046 (5)	−0.0035 (5)	−0.0041 (5)
O5	0.0511 (8)	0.0465 (8)	0.0239 (6)	0.0025 (6)	−0.0057 (6)	−0.0094 (6)
O6	0.0857 (13)	0.0733 (12)	0.0385 (8)	0.0311 (10)	−0.0203 (8)	−0.0070 (8)
O7	0.0738 (14)	0.0918 (16)	0.0666 (13)	0.0322 (12)	−0.0082 (10)	−0.0023 (11)
O8	0.0623 (14)	0.117 (2)	0.0876 (18)	0.0195 (14)	−0.0092 (12)	−0.0105 (16)
Zn1	0.02701 (12)	0.03025 (12)	0.01951 (11)	−0.00071 (8)	−0.00229 (7)	−0.00138 (7)

Geometric parameters (Å, º)

C1—C2	1.478 (3)	C17—C18	1.482 (3)
C1—H1A	0.9600	C17—H17A	0.9600
C1—H1B	0.9600	C17—H17B	0.9600
C1—H1C	0.9600	C17—H17C	0.9600
C2—N1	1.331 (2)	C18—N4	1.327 (2)
C2—N2	1.355 (2)	C18—N3	1.348 (2)
C3—C4	1.344 (3)	C19—C20	1.343 (3)
C3—N1	1.379 (3)	C19—N4	1.376 (2)
C3—H3	0.9300	C19—H19	0.9300
C4—N2	1.383 (3)	C20—N3	1.372 (3)
C4—H4	0.9300	C20—H20	0.9300
C5—C10	1.381 (3)	C21—O3	1.224 (2)
C5—C6	1.382 (3)	C21—O2	1.284 (2)
C5—N2	1.433 (2)	C21—C22	1.479 (2)
C6—C7	1.386 (3)	C22—C23	1.341 (3)
C6—H6	0.9300	C22—O4	1.366 (2)
C7—C8	1.380 (3)	C23—C24	1.414 (3)
C7—H7	0.9300	C23—H23	0.9300
C8—O1	1.380 (2)	C24—C25	1.348 (3)
C8—C9	1.386 (3)	C24—H24	0.9300
C9—C10	1.377 (3)	C25—O4	1.361 (2)
C9—H9	0.9300	C25—C26	1.487 (2)
C10—H10	0.9300	C26—O6	1.225 (3)
C11—C12	1.376 (3)	C26—O5	1.268 (2)
C11—C16	1.378 (3)	Zn1—N1	1.9951 (17)
C11—O1	1.387 (2)	N4—Zn1^i	2.0092 (17)
C12—C13	1.389 (3)	Zn1—O2	1.9516 (14)
C12—H12	0.9300	O5—Zn1^ii	1.9532 (15)
C13—C14	1.375 (3)	O7—H7B	0.8500
C13—H13	0.9300	O7—H7A	0.8499
C14—C15	1.376 (3)	O8—H8B	0.8500
C14—N3	1.443 (2)	O8—H8A	0.8501
C15—C16	1.388 (3)	Zn1—O5^iii	1.9532 (15)
C15—H15	0.9300	Zn1—N4^iv	2.0093 (17)
C16—H16	0.9300
C2—C1—H1A	109.5	C18—C17—H17C	109.5
C2—C1—H1B	109.5	H17A—C17—H17C	109.5
H1A—C1—H1B	109.5	H17B—C17—H17C	109.5
C2—C1—H1C	109.5	N4—C18—N3	109.79 (16)
H1A—C1—H1C	109.5	N4—C18—C17	126.17 (17)
H1B—C1—H1C	109.5	N3—C18—C17	123.99 (17)
N1—C2—N2	109.37 (17)	C20—C19—N4	109.21 (17)
N1—C2—C1	126.00 (18)	C20—C19—H19	125.4
N2—C2—C1	124.62 (17)	N4—C19—H19	125.4
C4—C3—N1	109.32 (17)	C19—C20—N3	106.63 (17)
C4—C3—H3	125.3	C19—C20—H20	126.7
N1—C3—H3	125.3	N3—C20—H20	126.7
C3—C4—N2	106.41 (17)	O3—C21—O2	125.10 (17)
C3—C4—H4	126.8	O3—C21—C22	121.77 (16)
N2—C4—H4	126.8	O2—C21—C22	113.12 (17)
C10—C5—C6	120.35 (17)	C23—C22—O4	110.29 (15)
C10—C5—N2	118.68 (17)	C23—C22—C21	131.80 (17)
C6—C5—N2	120.96 (17)	O4—C22—C21	117.88 (16)
C5—C6—C7	120.11 (18)	C22—C23—C24	106.72 (17)
C5—C6—H6	119.9	C22—C23—H23	126.6
C7—C6—H6	119.9	C24—C23—H23	126.6
C8—C7—C6	119.08 (18)	C25—C24—C23	106.46 (18)
C8—C7—H7	120.5	C25—C24—H24	126.8
C6—C7—H7	120.5	C23—C24—H24	126.8
O1—C8—C7	125.75 (17)	C24—C25—O4	110.27 (16)
O1—C8—C9	113.30 (17)	C24—C25—C26	131.80 (17)
C7—C8—C9	120.87 (17)	O4—C25—C26	117.92 (16)
C10—C9—C8	119.66 (18)	O6—C26—O5	126.03 (18)
C10—C9—H9	120.2	O6—C26—C25	120.80 (18)
C8—C9—H9	120.2	O5—C26—C25	113.14 (17)
C9—C10—C5	119.89 (17)	C2—N1—C3	107.01 (15)
C9—C10—H10	120.1	C2—N1—Zn1	127.89 (13)
C5—C10—H10	120.1	C3—N1—Zn1	122.35 (12)
C12—C11—C16	121.04 (18)	C2—N2—C4	107.88 (15)
C12—C11—O1	124.09 (19)	C2—N2—C5	127.19 (16)
C16—C11—O1	114.61 (18)	C4—N2—C5	124.88 (16)
C11—C12—C13	118.92 (19)	C18—N3—C20	107.74 (15)
C11—C12—H12	120.5	C18—N3—C14	125.90 (16)
C13—C12—H12	120.5	C20—N3—C14	126.18 (16)
C14—C13—C12	120.05 (19)	C18—N4—C19	106.61 (15)
C14—C13—H13	120.0	C18—N4—Zn1^i	125.24 (13)
C12—C13—H13	120.0	C19—N4—Zn1^i	123.73 (12)
C13—C14—C15	121.05 (18)	C8—O1—C11	123.80 (16)
C13—C14—N3	119.47 (17)	C21—O2—Zn1	111.75 (12)
C15—C14—N3	119.47 (17)	C25—O4—C22	106.26 (14)
C14—C15—C16	119.0 (2)	C26—O5—Zn1^ii	122.17 (12)
C14—C15—H15	120.5	H7B—O7—H7A	108.5
C16—C15—H15	120.5	H8B—O8—H8A	107.9
C11—C16—C15	119.9 (2)	O2—Zn1—O5^iii	105.75 (7)
C11—C16—H16	120.0	O2—Zn1—N1	105.60 (6)
C15—C16—H16	120.0	O5^iii—Zn1—N1	118.58 (6)
C18—C17—H17A	109.5	O2—Zn1—N4^iv	112.45 (6)
C18—C17—H17B	109.5	O5^iii—Zn1—N4^iv	95.63 (6)
H17A—C17—H17B	109.5	N1—Zn1—N4^iv	118.32 (6)
N1—C3—C4—N2	−0.7 (2)	C4—C3—N1—Zn1	162.82 (14)
C10—C5—C6—C7	−1.3 (3)	N1—C2—N2—C4	−0.7 (2)
N2—C5—C6—C7	179.90 (19)	C1—C2—N2—C4	178.7 (2)
C5—C6—C7—C8	0.1 (3)	N1—C2—N2—C5	−178.03 (17)
C6—C7—C8—O1	178.1 (2)	C1—C2—N2—C5	1.3 (3)
C6—C7—C8—C9	1.5 (3)	C3—C4—N2—C2	0.8 (2)
O1—C8—C9—C10	−178.96 (19)	C3—C4—N2—C5	178.27 (18)
C7—C8—C9—C10	−2.0 (3)	C10—C5—N2—C2	119.2 (2)
C8—C9—C10—C5	0.7 (3)	C6—C5—N2—C2	−62.0 (3)
C6—C5—C10—C9	0.9 (3)	C10—C5—N2—C4	−57.7 (3)
N2—C5—C10—C9	179.71 (18)	C6—C5—N2—C4	121.0 (2)
C16—C11—C12—C13	0.8 (3)	N4—C18—N3—C20	1.1 (2)
O1—C11—C12—C13	174.7 (2)	C17—C18—N3—C20	−176.5 (2)
C11—C12—C13—C14	−1.3 (3)	N4—C18—N3—C14	−174.28 (17)
C12—C13—C14—C15	0.7 (3)	C17—C18—N3—C14	8.1 (3)
C12—C13—C14—N3	−178.96 (18)	C19—C20—N3—C18	−0.8 (2)
C13—C14—C15—C16	0.5 (4)	C19—C20—N3—C14	174.59 (18)
N3—C14—C15—C16	−179.9 (2)	C13—C14—N3—C18	84.1 (2)
C12—C11—C16—C15	0.3 (4)	C15—C14—N3—C18	−95.6 (3)
O1—C11—C16—C15	−174.1 (2)	C13—C14—N3—C20	−90.5 (3)
C14—C15—C16—C11	−1.0 (4)	C15—C14—N3—C20	89.8 (3)
N4—C19—C20—N3	0.2 (2)	N3—C18—N4—C19	−1.0 (2)
O3—C21—C22—C23	−179.9 (2)	C17—C18—N4—C19	176.6 (2)
O2—C21—C22—C23	0.7 (3)	N3—C18—N4—Zn1^i	155.97 (13)
O3—C21—C22—O4	1.9 (3)	C17—C18—N4—Zn1^i	−26.4 (3)
O2—C21—C22—O4	−177.48 (15)	C20—C19—N4—C18	0.5 (2)
O4—C22—C23—C24	0.1 (2)	C20—C19—N4—Zn1^i	−156.93 (15)
C21—C22—C23—C24	−178.14 (19)	C7—C8—O1—C11	11.0 (4)
C22—C23—C24—C25	0.1 (3)	C9—C8—O1—C11	−172.2 (2)
C23—C24—C25—O4	−0.3 (2)	C12—C11—O1—C8	45.3 (3)
C23—C24—C25—C26	178.5 (2)	C16—C11—O1—C8	−140.5 (2)
C24—C25—C26—O6	173.9 (2)	O3—C21—O2—Zn1	−19.7 (2)
O4—C25—C26—O6	−7.4 (3)	C22—C21—O2—Zn1	159.66 (12)
C24—C25—C26—O5	−4.4 (3)	C24—C25—O4—C22	0.4 (2)
O4—C25—C26—O5	174.30 (16)	C26—C25—O4—C22	−178.61 (16)
N2—C2—N1—C3	0.2 (2)	C23—C22—O4—C25	−0.3 (2)
C1—C2—N1—C3	−179.1 (2)	C21—C22—O4—C25	178.23 (15)
N2—C2—N1—Zn1	−161.01 (13)	O6—C26—O5—Zn1^ii	20.8 (3)
C1—C2—N1—Zn1	19.7 (3)	C25—C26—O5—Zn1^ii	−161.01 (12)
C4—C3—N1—C2	0.3 (2)

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

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
O8—H8A···O7^v	0.85	2.08	2.896 (4)	161
O8—H8B···O6	0.85	2.00	2.818 (3)	161
O7—H7A···O8	0.85	1.96	2.813 (4)	176
O7—H7B···O3	0.85	1.94	2.785 (3)	176
C16—H16···O4^vi	0.93	2.49	3.407 (3)	168
C15—H15···O8^vii	0.93	2.62	3.266 (4)	127
C9—H9···O2^vi	0.93	2.53	3.421 (3)	162
C6—H6···O7	0.93	2.50	3.429 (3)	175
C3—H3···O6^iii	0.93	2.58	3.230 (3)	127
O8—H8B···O6	0.85	2.00	2.818 (3)	161
O7—H7A···O8	0.85	1.96	2.813 (4)	176
O7—H7B···O3	0.85	1.94	2.785 (3)	176
C6—H6···O7	0.93	2.50	3.429 (3)	175
C3—H3···O6^iii	0.93	2.58	3.230 (3)	127
C9—H9···O2^vi	0.93	2.53	3.421 (3)	162
C16—H16···O4^vi	0.93	2.49	3.407 (3)	168
C15—H15···O8^vii	0.93	2.62	3.266 (4)	127
O8—H8A···O7^v	0.85	2.08	2.896 (4)	161
C3—H3···O6^iii	0.93	2.58	3.230 (3)	127
C6—H6···O7	0.93	2.50	3.429 (3)	175
C9—H9···O2^vi	0.93	2.53	3.421 (3)	162
C15—H15···O8^vii	0.93	2.62	3.266 (4)	127
C16—H16···O4^vi	0.93	2.49	3.407 (3)	168
O7—H7B···O3	0.85	1.94	2.785 (3)	176
O7—H7A···O8	0.85	1.96	2.813 (4)	176
O8—H8B···O6	0.85	2.00	2.818 (3)	161
O8—H8A···O7^v	0.85	2.08	2.896 (4)	161

Symmetry codes: (iii) x, −y+3/2, z−1/2; (v) −x+1, −y+1, −z+1; (vi) x+1, y, z; (vii) −x+2, −y+1, −z+1.