Crystal structure of the tri­ethyl­ammonium salt of 3-[(4-hy­droxy-3-meth­oxy­phen­yl)(4-hy­droxy-2-oxo-2H-chromen-3-yl)meth­yl]-2-oxo-2H-chromen-4-olate

3,3′-[(3-Meth­oxy-4-hy­droxy­phen­yl)methanedi­yl]bis­(4-hy­droxy-2H-chromen-2-one), the 4-hy­droxy-3-meth­oxy­phenyl-substituted derivative of dicoumarol, was deprotonated by the addition of tri­ethyl­amine, yielding the respective ammonium salt which was crystallized from a methanol solution. The deprotonated dicoumarol derivative exhibits an intra­molecular negative charge-assisted hydrogen bond between the deprotonated and non-deprotonated alcohol functions of the coumarol substituents.

Key indicators

• Single-crystal X-ray study
• T = 170 K
• Mean [sigma](C-C) = 0.002 Å
• R factor = 0.044
• wR factor = 0.122
• Data-to-parameter ratio = 20.0

checkCIF/PLATON results

No syntax errors found



Alert level C
PLAT303_ALERT_2_C Full Occupancy Atom H3O       with # Connections       2.00 Check
PLAT601_ALERT_2_C Structure Contains Solvent Accessible VOIDS of .         32 Ang   3
PLAT906_ALERT_3_C Large K Value in the Analysis of Variance ......      3.222 Check
PLAT910_ALERT_3_C Missing # of FCF Reflection(s) Below Theta(Min).         10 Note

Alert level G
PLAT042_ALERT_1_G Calc. and Reported MoietyFormula Strings  Differ     Please Check
PLAT231_ALERT_4_G Hirshfeld Test (Solvent)  C31      --C32       .        5.8 s.u.
PLAT912_ALERT_4_G Missing # of FCF Reflections Above STh/L=  0.600        157 Note
PLAT978_ALERT_2_G Number C-C Bonds with Positive Residual Density.          2 Info

   0 ALERT level A = Most likely a serious problem - resolve or explain
   0 ALERT level B = A potentially serious problem, consider carefully
   4 ALERT level C = Check. Ensure it is not caused by an omission or oversight
   4 ALERT level G = General information/check it is not something unexpected

   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
   2 ALERT type 3 Indicator that the structure quality may be low
   2 ALERT type 4 Improvement, methodology, query or suggestion
   0 ALERT type 5 Informative message, check

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Computing details

Data collection: X-AREA (Stoe & Cie, 2010); cell refinement: X-AREA (Stoe & Cie, 2010); data reduction: X-AREA (Stoe & Cie, 2010); program(s) used to solve structure: SHELXT2016 (Sheldrick, 2015a); program(s) used to refine structure: SHELXL2016 (Sheldrick, 2015b); molecular graphics: XP in SHELXTL (Sheldrick, 2008); software used to prepare material for publication: CIFTAB (Sheldrick, 2008) and Mercury (Macrae et al., 2006).

Triethylammonium 3-[(4-hydroxy-3-methoxyphenyl)(4-hydroxy-2-oxo-2H-chromen-3-yl)methyl]-2-oxo-2H-chromen-4-olate

Crystal data

C6H16N^+·C26H17O8^−	F(000) = 2368
Mr = 559.59	Dx = 1.326 Mg m^−3
Monoclinic, C2/c	Mo Kα radiation, λ = 0.71073 Å
a = 19.408 (4) Å	Cell parameters from 31667 reflections
b = 13.518 (3) Å	θ = 6.3–59.2°
c = 21.714 (4) Å	µ = 0.10 mm^−1
β = 100.16 (3)°	T = 170 K
V = 5607 (2) Å^3	Prism, colourless
Z = 8	0.44 × 0.39 × 0.37 mm

Data collection

Stoe IPDS2T diffractometer	7726 independent reflections
Radiation source: fine-focus sealed tube	4433 reflections with I > 2σ(I)
Detector resolution: 6.67 pixels mm^-1	Rint = 0.054
ω scans	θmax = 29.6°, θmin = 3.2°
Absorption correction: numerical (X-RED32 and X-SHAPE; Stoe & Cie, 2010)	h = −26→26
Tmin = 0.784, Tmax = 0.927	k = −18→18
31033 measured reflections	l = −29→30

Refinement

Refinement on F^2	0 restraints
Least-squares matrix: full	Hydrogen site location: mixed
R[F^2 > 2σ(F^2)] = 0.044	H atoms treated by a mixture of independent and constrained refinement
wR(F^2) = 0.122	w = 1/[σ^2(Fo^2) + (0.0718P)^2] where P = (Fo^2 + 2Fc^2)/3
S = 0.90	(Δ/σ)max < 0.001
7726 reflections	Δρmax = 0.44 e Å^−3
386 parameters	Δρmin = −0.26 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
O1	0.65404 (7)	0.33340 (8)	0.59806 (5)	0.0450 (3)
O2	0.71609 (6)	0.37291 (7)	0.52747 (5)	0.0351 (2)
O3	0.72176 (6)	0.66489 (7)	0.57698 (5)	0.0349 (2)
O4	0.54117 (6)	0.42562 (8)	0.68855 (5)	0.0392 (3)
O5	0.46745 (5)	0.54780 (8)	0.66496 (5)	0.0413 (3)
O6	0.61390 (6)	0.72322 (8)	0.60507 (5)	0.0380 (3)
O7	0.89787 (6)	0.52052 (8)	0.78148 (5)	0.0432 (3)
O8	0.88267 (5)	0.69683 (8)	0.82643 (5)	0.0382 (3)
C1	0.65911 (7)	0.52333 (10)	0.65646 (6)	0.0283 (3)
H1	0.653226	0.456518	0.674616	0.034*
C2	0.68601 (7)	0.50216 (10)	0.59576 (6)	0.0274 (3)
C3	0.68308 (8)	0.40112 (10)	0.57585 (6)	0.0307 (3)
C4	0.75438 (8)	0.43890 (10)	0.49954 (7)	0.0304 (3)
C5	0.79254 (9)	0.40104 (12)	0.45636 (7)	0.0380 (3)
H5	0.791402	0.332382	0.446889	0.046*
C6	0.83190 (9)	0.46504 (12)	0.42771 (7)	0.0397 (4)
H6	0.859256	0.440327	0.398885	0.048*
C7	0.83193 (9)	0.56603 (12)	0.44068 (7)	0.0391 (4)
H7	0.858278	0.609993	0.419785	0.047*
C8	0.79410 (8)	0.60231 (11)	0.48347 (7)	0.0340 (3)
H8	0.794209	0.671288	0.491881	0.041*
C9	0.75550 (7)	0.53842 (10)	0.51466 (6)	0.0282 (3)
C10	0.71880 (7)	0.57089 (10)	0.56401 (6)	0.0280 (3)
C11	0.58739 (7)	0.57065 (11)	0.64990 (6)	0.0306 (3)
C12	0.53443 (8)	0.51111 (11)	0.66936 (7)	0.0334 (3)
C13	0.45011 (8)	0.64011 (12)	0.64179 (7)	0.0384 (4)
C14	0.38105 (9)	0.66885 (15)	0.63775 (9)	0.0515 (4)
H14	0.347869	0.626144	0.651362	0.062*
C15	0.36156 (10)	0.76085 (16)	0.61355 (10)	0.0577 (5)
H15	0.314319	0.781672	0.610423	0.069*
C16	0.40959 (9)	0.82347 (15)	0.59370 (9)	0.0517 (5)
H16	0.395311	0.886758	0.577164	0.062*
C17	0.47810 (9)	0.79387 (12)	0.59795 (8)	0.0420 (4)
H17	0.511084	0.836923	0.584344	0.050*
C18	0.49943 (8)	0.70091 (11)	0.62216 (7)	0.0352 (3)
C19	0.57071 (7)	0.66420 (11)	0.62576 (7)	0.0313 (3)
C20	0.71563 (7)	0.57348 (10)	0.70423 (6)	0.0282 (3)
C21	0.77965 (8)	0.52424 (10)	0.72074 (7)	0.0315 (3)
H21	0.785784	0.461518	0.702725	0.038*
C22	0.83384 (7)	0.56465 (11)	0.76247 (6)	0.0313 (3)
C23	0.82595 (7)	0.65759 (11)	0.78824 (6)	0.0303 (3)
C24	0.76243 (8)	0.70469 (11)	0.77388 (7)	0.0338 (3)
H24	0.756016	0.766884	0.792446	0.041*
C25	0.70744 (8)	0.66260 (11)	0.73256 (7)	0.0331 (3)
H25	0.663662	0.695791	0.723776	0.040*
C26	0.90262 (10)	0.41779 (13)	0.76835 (9)	0.0543 (5)
H26A	0.865134	0.382110	0.783783	0.081*
H26B	0.948123	0.392467	0.789170	0.081*
H26C	0.897890	0.408094	0.723074	0.081*
H3O	0.6704 (13)	0.6889 (17)	0.5951 (11)	0.085 (7)*
H8O	0.8688 (10)	0.7456 (14)	0.8472 (9)	0.047 (5)*
N1	0.43844 (8)	0.30039 (12)	0.62696 (7)	0.0470 (4)
C27	0.44835 (9)	0.20824 (14)	0.66564 (9)	0.0509 (5)
H27A	0.431136	0.220287	0.705272	0.061*
H27B	0.499039	0.193640	0.676315	0.061*
C28	0.41125 (13)	0.11883 (15)	0.63391 (11)	0.0694 (6)
H28A	0.360606	0.130354	0.626276	0.104*
H28B	0.422180	0.060744	0.660876	0.104*
H28C	0.426885	0.107345	0.593994	0.104*
C29	0.46749 (11)	0.28595 (16)	0.56641 (9)	0.0583 (5)
H29A	0.512240	0.249257	0.576127	0.070*
H29B	0.434245	0.244931	0.537270	0.070*
C30	0.47967 (13)	0.38019 (16)	0.53470 (9)	0.0651 (6)
H30A	0.434859	0.413819	0.520966	0.098*
H30B	0.501585	0.366045	0.498311	0.098*
H30C	0.510589	0.422827	0.563915	0.098*
C31	0.36666 (10)	0.34013 (16)	0.61423 (10)	0.0604 (5)
H31A	0.334931	0.289439	0.591806	0.072*
H31B	0.365407	0.398452	0.586472	0.072*
C32	0.34037 (11)	0.3698 (2)	0.67264 (10)	0.0723 (7)
H32A	0.331448	0.310448	0.695904	0.108*
H32B	0.296877	0.407609	0.661328	0.108*
H32C	0.375635	0.410813	0.698784	0.108*
H1N	0.4677 (11)	0.3515 (15)	0.6501 (10)	0.064 (6)*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
O1	0.0646 (8)	0.0275 (5)	0.0459 (6)	−0.0090 (5)	0.0180 (6)	0.0021 (5)
O2	0.0467 (6)	0.0250 (5)	0.0350 (5)	−0.0026 (4)	0.0105 (5)	−0.0019 (4)
O3	0.0372 (6)	0.0243 (5)	0.0460 (6)	−0.0043 (4)	0.0146 (5)	−0.0036 (4)
O4	0.0366 (6)	0.0435 (6)	0.0367 (5)	−0.0117 (5)	0.0039 (4)	0.0044 (5)
O5	0.0263 (5)	0.0525 (7)	0.0458 (6)	−0.0047 (5)	0.0080 (5)	0.0017 (5)
O6	0.0306 (6)	0.0333 (5)	0.0511 (6)	0.0003 (4)	0.0094 (5)	0.0053 (5)
O7	0.0334 (6)	0.0446 (6)	0.0470 (6)	0.0127 (5)	−0.0056 (5)	−0.0110 (5)
O8	0.0284 (6)	0.0417 (6)	0.0427 (6)	−0.0011 (5)	0.0011 (5)	−0.0143 (5)
C1	0.0270 (7)	0.0281 (7)	0.0295 (7)	−0.0029 (5)	0.0042 (5)	0.0015 (5)
C2	0.0250 (7)	0.0277 (6)	0.0282 (6)	−0.0012 (5)	0.0012 (5)	0.0000 (5)
C3	0.0330 (8)	0.0278 (7)	0.0300 (7)	−0.0009 (6)	0.0023 (6)	0.0018 (5)
C4	0.0316 (7)	0.0284 (7)	0.0299 (7)	−0.0019 (6)	0.0021 (6)	0.0012 (5)
C5	0.0440 (9)	0.0333 (8)	0.0368 (8)	0.0032 (7)	0.0074 (7)	−0.0039 (6)
C6	0.0410 (9)	0.0470 (9)	0.0326 (8)	0.0028 (7)	0.0104 (7)	−0.0022 (6)
C7	0.0401 (9)	0.0413 (9)	0.0373 (8)	−0.0039 (7)	0.0105 (7)	0.0012 (6)
C8	0.0344 (8)	0.0315 (7)	0.0362 (7)	−0.0028 (6)	0.0068 (6)	0.0004 (6)
C9	0.0266 (7)	0.0275 (6)	0.0289 (7)	−0.0003 (5)	0.0002 (5)	0.0008 (5)
C10	0.0255 (7)	0.0258 (6)	0.0311 (7)	−0.0009 (5)	0.0008 (5)	−0.0003 (5)
C11	0.0256 (7)	0.0362 (7)	0.0292 (7)	−0.0039 (6)	0.0031 (5)	−0.0028 (6)
C12	0.0283 (7)	0.0427 (8)	0.0284 (7)	−0.0058 (6)	0.0031 (6)	−0.0041 (6)
C13	0.0278 (8)	0.0513 (9)	0.0352 (8)	−0.0002 (7)	0.0032 (6)	−0.0065 (7)
C14	0.0292 (8)	0.0706 (12)	0.0546 (10)	0.0016 (8)	0.0072 (7)	−0.0067 (9)
C15	0.0303 (9)	0.0755 (13)	0.0647 (12)	0.0120 (9)	0.0010 (8)	−0.0129 (10)
C16	0.0396 (10)	0.0584 (11)	0.0526 (10)	0.0135 (9)	−0.0045 (8)	−0.0088 (8)
C17	0.0366 (9)	0.0457 (9)	0.0414 (8)	0.0059 (7)	0.0003 (7)	−0.0054 (7)
C18	0.0285 (8)	0.0433 (8)	0.0318 (7)	0.0017 (6)	−0.0001 (6)	−0.0067 (6)
C19	0.0271 (7)	0.0347 (7)	0.0313 (7)	−0.0037 (6)	0.0032 (6)	−0.0034 (6)
C20	0.0268 (7)	0.0301 (7)	0.0280 (6)	−0.0018 (6)	0.0055 (5)	0.0003 (5)
C21	0.0345 (8)	0.0289 (7)	0.0302 (7)	0.0038 (6)	0.0028 (6)	−0.0027 (5)
C22	0.0266 (7)	0.0355 (7)	0.0307 (7)	0.0043 (6)	0.0023 (5)	−0.0012 (6)
C23	0.0260 (7)	0.0351 (7)	0.0288 (7)	−0.0037 (6)	0.0025 (5)	−0.0033 (6)
C24	0.0315 (8)	0.0311 (7)	0.0385 (8)	0.0007 (6)	0.0056 (6)	−0.0081 (6)
C25	0.0261 (7)	0.0340 (7)	0.0384 (8)	0.0030 (6)	0.0037 (6)	−0.0033 (6)
C26	0.0536 (11)	0.0461 (10)	0.0575 (11)	0.0231 (9)	−0.0055 (9)	−0.0063 (8)
N1	0.0418 (8)	0.0546 (8)	0.0391 (7)	−0.0160 (7)	−0.0081 (6)	0.0083 (6)
C27	0.0362 (9)	0.0638 (12)	0.0495 (10)	−0.0042 (8)	−0.0010 (8)	0.0164 (9)
C28	0.0777 (15)	0.0541 (12)	0.0745 (14)	−0.0127 (11)	0.0082 (12)	0.0119 (10)
C29	0.0603 (12)	0.0710 (13)	0.0402 (9)	−0.0151 (10)	−0.0002 (8)	−0.0013 (9)
C30	0.0820 (15)	0.0759 (14)	0.0356 (9)	−0.0231 (12)	0.0051 (9)	0.0010 (9)
C31	0.0511 (11)	0.0590 (12)	0.0622 (12)	−0.0008 (9)	−0.0145 (9)	0.0007 (10)
C32	0.0476 (12)	0.1114 (19)	0.0579 (12)	−0.0237 (12)	0.0092 (10)	0.0128 (12)

Geometric parameters (Å, º)

O1—C3	1.2183 (17)	C16—C17	1.376 (2)
O2—C4	1.3692 (17)	C16—H16	0.9500
O2—C3	1.3773 (18)	C17—C18	1.396 (2)
O3—C10	1.3005 (16)	C17—H17	0.9500
O3—H3O	1.18 (3)	C18—C19	1.459 (2)
O4—C12	1.2275 (18)	C20—C25	1.375 (2)
O5—C13	1.365 (2)	C20—C21	1.399 (2)
O5—C12	1.3789 (18)	C21—C22	1.375 (2)
O6—C19	1.2939 (17)	C21—H21	0.9500
O6—H3O	1.24 (3)	C22—C23	1.395 (2)
O7—C22	1.3745 (17)	C23—C24	1.374 (2)
O7—C26	1.424 (2)	C24—C25	1.389 (2)
O8—C23	1.3634 (17)	C24—H24	0.9500
O8—H8O	0.869 (19)	C25—H25	0.9500
C1—C11	1.516 (2)	C26—H26A	0.9800
C1—C2	1.5277 (19)	C26—H26B	0.9800
C1—C20	1.5287 (19)	C26—H26C	0.9800
C1—H1	1.0000	N1—C31	1.473 (2)
C2—C10	1.3779 (19)	N1—C27	1.496 (2)
C2—C3	1.4307 (19)	N1—C29	1.532 (3)
C4—C9	1.384 (2)	N1—H1N	0.98 (2)
C4—C5	1.391 (2)	C27—C28	1.510 (3)
C5—C6	1.374 (2)	C27—H27A	0.9900
C5—H5	0.9500	C27—H27B	0.9900
C6—C7	1.394 (2)	C28—H28A	0.9800
C6—H6	0.9500	C28—H28B	0.9800
C7—C8	1.372 (2)	C28—H28C	0.9800
C7—H7	0.9500	C29—C30	1.487 (3)
C8—C9	1.395 (2)	C29—H29A	0.9900
C8—H8	0.9500	C29—H29B	0.9900
C9—C10	1.455 (2)	C30—H30A	0.9800
C11—C19	1.385 (2)	C30—H30B	0.9800
C11—C12	1.427 (2)	C30—H30C	0.9800
C13—C14	1.383 (2)	C31—C32	1.503 (3)
C13—C18	1.385 (2)	C31—H31A	0.9900
C14—C15	1.377 (3)	C31—H31B	0.9900
C14—H14	0.9500	C32—H32A	0.9800
C15—C16	1.383 (3)	C32—H32B	0.9800
C15—H15	0.9500	C32—H32C	0.9800
C4—O2—C3	121.30 (11)	C25—C20—C21	118.02 (13)
C10—O3—H3O	109.5 (11)	C25—C20—C1	124.51 (13)
C13—O5—C12	121.49 (12)	C21—C20—C1	117.47 (12)
C19—O6—H3O	118.4 (11)	C22—C21—C20	121.43 (13)
C22—O7—C26	116.76 (13)	C22—C21—H21	119.3
C23—O8—H8O	108.6 (12)	C20—C21—H21	119.3
C11—C1—C2	116.48 (12)	O7—C22—C21	124.85 (13)
C11—C1—C20	114.44 (12)	O7—C22—C23	115.34 (12)
C2—C1—C20	110.79 (11)	C21—C22—C23	119.80 (13)
C11—C1—H1	104.5	O8—C23—C24	123.63 (13)
C2—C1—H1	104.5	O8—C23—C22	117.41 (13)
C20—C1—H1	104.5	C24—C23—C22	118.96 (13)
C10—C2—C3	119.32 (13)	C23—C24—C25	120.88 (13)
C10—C2—C1	124.31 (12)	C23—C24—H24	119.6
C3—C2—C1	115.99 (12)	C25—C24—H24	119.6
O1—C3—O2	113.83 (12)	C20—C25—C24	120.78 (13)
O1—C3—C2	126.45 (14)	C20—C25—H25	119.6
O2—C3—C2	119.72 (12)	C24—C25—H25	119.6
O2—C4—C9	121.00 (13)	O7—C26—H26A	109.5
O2—C4—C5	117.01 (12)	O7—C26—H26B	109.5
C9—C4—C5	121.98 (14)	H26A—C26—H26B	109.5
C6—C5—C4	118.58 (14)	O7—C26—H26C	109.5
C6—C5—H5	120.7	H26A—C26—H26C	109.5
C4—C5—H5	120.7	H26B—C26—H26C	109.5
C5—C6—C7	120.38 (15)	C31—N1—C27	115.64 (15)
C5—C6—H6	119.8	C31—N1—C29	111.38 (15)
C7—C6—H6	119.8	C27—N1—C29	110.21 (15)
C8—C7—C6	120.37 (15)	C31—N1—H1N	106.5 (12)
C8—C7—H7	119.8	C27—N1—H1N	107.2 (12)
C6—C7—H7	119.8	C29—N1—H1N	105.2 (12)
C7—C8—C9	120.32 (14)	N1—C27—C28	114.01 (15)
C7—C8—H8	119.8	N1—C27—H27A	108.8
C9—C8—H8	119.8	C28—C27—H27A	108.8
C4—C9—C8	118.30 (14)	N1—C27—H27B	108.8
C4—C9—C10	118.59 (13)	C28—C27—H27B	108.8
C8—C9—C10	123.06 (13)	H27A—C27—H27B	107.6
O3—C10—C2	123.86 (13)	C27—C28—H28A	109.5
O3—C10—C9	116.45 (12)	C27—C28—H28B	109.5
C2—C10—C9	119.63 (12)	H28A—C28—H28B	109.5
C19—C11—C12	119.64 (13)	C27—C28—H28C	109.5
C19—C11—C1	124.77 (13)	H28A—C28—H28C	109.5
C12—C11—C1	115.57 (13)	H28B—C28—H28C	109.5
O4—C12—O5	113.87 (13)	C30—C29—N1	113.64 (17)
O4—C12—C11	126.33 (14)	C30—C29—H29A	108.8
O5—C12—C11	119.74 (13)	N1—C29—H29A	108.8
O5—C13—C14	116.94 (15)	C30—C29—H29B	108.8
O5—C13—C18	121.14 (14)	N1—C29—H29B	108.8
C14—C13—C18	121.90 (16)	H29A—C29—H29B	107.7
C15—C14—C13	118.40 (18)	C29—C30—H30A	109.5
C15—C14—H14	120.8	C29—C30—H30B	109.5
C13—C14—H14	120.8	H30A—C30—H30B	109.5
C14—C15—C16	121.12 (17)	C29—C30—H30C	109.5
C14—C15—H15	119.4	H30A—C30—H30C	109.5
C16—C15—H15	119.4	H30B—C30—H30C	109.5
C17—C16—C15	119.84 (18)	N1—C31—C32	112.94 (17)
C17—C16—H16	120.1	N1—C31—H31A	109.0
C15—C16—H16	120.1	C32—C31—H31A	109.0
C16—C17—C18	120.38 (18)	N1—C31—H31B	109.0
C16—C17—H17	119.8	C32—C31—H31B	109.0
C18—C17—H17	119.8	H31A—C31—H31B	107.8
C13—C18—C17	118.36 (15)	C31—C32—H32A	109.5
C13—C18—C19	118.82 (14)	C31—C32—H32B	109.5
C17—C18—C19	122.80 (15)	H32A—C32—H32B	109.5
O6—C19—C11	124.88 (13)	C31—C32—H32C	109.5
O6—C19—C18	115.97 (13)	H32A—C32—H32C	109.5
C11—C19—C18	119.14 (13)	H32B—C32—H32C	109.5

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
O3—H3O···O6	1.18 (3)	1.24 (3)	2.4139 (15)	169 (2)
O8—H8O···O1^i	0.869 (19)	1.789 (19)	2.6488 (16)	170.0 (18)
C27—H27B···O8^ii	0.99	2.31	3.257 (2)	161
N1—H1N···O4	0.98 (2)	1.82 (2)	2.7727 (19)	164.5 (18)

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