Tramadolium 2-chloro­benzoate

In the title mol­ecular salt, C₁₆H₂₆NO₂⁺·C₇H₄ClO₂⁻, {systematic name: [2-hy­droxy-2-(3-meth­oxy­phen­yl)cyclo­hexyl­meth­yl]di­methyl­ammonium 2-chloro­benzoate}, the cyclo­hexane ring of the cation exhibits a chair conformation with the aromatic and amine substituents in equatorial orientations and the hydroxyl group in an axial orientation. In the anion, the dihedral angle between the aromatic ring and the carboxyl­ate group is 39.16 (13)°. In the crystal, the cations are linked to the anions by O—H...O, N—H...O and C—H...O hydrogen bonds, generating [010] chains. Further C—H...O and C—H...π inter­actions are also observed, which link the chains into a three-dimensional framework.

Key indicators

• Single-crystal X-ray study
• T = 293 K
• Mean [sigma](C-C) = 0.003 Å
• R factor = 0.047
• wR factor = 0.111
• Data-to-parameter ratio = 14.1

checkCIF/PLATON results

No syntax errors found



Alert level B
PLAT029_ALERT_3_B _diffrn_measured_fraction_theta_full Low .......      0.946 Note

Alert level C
PLAT906_ALERT_3_C Large K value in the Analysis of Variance ......      8.019 Check
PLAT910_ALERT_3_C Missing # of FCF Reflection(s) Below Th(Min) ...          7 Report
PLAT911_ALERT_3_C Missing # FCF Refl Between THmin & STh/L=  0.600        208 Report

Alert level G
PLAT007_ALERT_5_G Number of Unrefined Donor-H Atoms ..............          2 Report
PLAT042_ALERT_1_G Calc. and Reported MoietyFormula Strings  Differ     Please Check
PLAT066_ALERT_1_G Predicted and Reported Tmin&Tmax Range Identical          ? Check
PLAT199_ALERT_1_G Reported _cell_measurement_temperature ..... (K)        293 Check
PLAT200_ALERT_1_G Reported   _diffrn_ambient_temperature ..... (K)        293 Check
PLAT793_ALERT_4_G The Model has Chirality at C9      (Centro SPGR)          S Verify
PLAT793_ALERT_4_G The Model has Chirality at C15     (Centro SPGR)          S Verify
PLAT909_ALERT_3_G Percentage of Observed Data at Theta(Max) Still          48 %
PLAT912_ALERT_4_G Missing # of FCF Reflections Above STh/L=  0.600          3 Note

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

   4 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
   0 ALERT type 2 Indicator that the structure model may be wrong or deficient
   5 ALERT type 3 Indicator that the structure quality may be low
   3 ALERT type 4 Improvement, methodology, query or suggestion
   1 ALERT type 5 Informative message, check


checkCIF publication errors

Alert level A
PUBL024_ALERT_1_A The number of authors is greater than 5.
              Please specify the role of each of the co-authors
              for your paper.

Author Response: This research work is a colloborative work between two universities and costituent colleges. MKS performed X-ray diffraction experiments SSN synthesized the molecule NP and SBP were involved in the desiging the synthesis and assisted in synthesizing molecule NKL and KB were involved in the manuscript preparation and refinement of the molecule.

   1 ALERT level A = Data missing that is essential or data in wrong format
   0 ALERT level G = General alerts. Data that may be required is missing

---

Related literature

For a related structure, see: Sheshadri et al. (2015).

S1. Experimental

Tramadol (3 g, 0.01 mol) and 2-chloro benzoic acid (1 g, 0.01 mol) were each dissolved in 10 ml of ethanol. The solutions were mixed and stirred in a beaker at 300 K for 30 min. The mixture was kept aside for three days at room temperature. Colourless blocks were formed and one was used for the data collection.

S2. Refinement

Crystal data, data collection and structure refinement details are summarized in Table 2.

Structure description

A view of the title molecular salt is shown in Fig. 1. Details of the hydrogen bonds and C—H···π interactions are given in Table 1 and illustrated in Fig. 2. For a related structure, see: Sheshadri et al. (2015).

Computing details

Data collection: CrystalClear SM Expert (Rigaku, 2011); cell refinement: CrystalClear SM Expert (Rigaku, 2011); data reduction: CrystalClear SM Expert (Rigaku, 2011); program(s) used to solve structure: SHELXS1997 (Sheldrick, 2008); program(s) used to refine structure: SHELXL2014/7 (Sheldrick, 2015); molecular graphics: Mercury (Macrae et al., 2008); software used to prepare material for publication: OLEX2 (Dolomanov et al., 2009).

Figures

	Fig. 1. A view of the title compound with displacement ellipsoids drawn at the 50% probability level. The intramolecular hydrogen bond is drawn as a dashed line.
	Fig. 2. A view along the a axis of the packing of the title compound. Hydrogen bonds are drawn as a dashed lines.

[2-Hydroxy-2-(3-methoxyphenyl)cyclohexylmethyl]dimethylammonium 2-chlorobenzoate

Crystal data

C16H26NO2^+·C7H4ClO2^−	Z = 2
Mr = 419.93	F(000) = 448
Triclinic, P1	Dx = 1.277 Mg m^−3
a = 9.205 (6) Å	Mo Kα radiation, λ = 0.71075 Å
b = 9.688 (7) Å	Cell parameters from 3759 reflections
c = 12.943 (9) Å	θ = 3.1–25.3°
α = 104.871 (11)°	µ = 0.20 mm^−1
β = 91.465 (7)°	T = 293 K
γ = 100.983 (12)°	Block, colourless
V = 1091.8 (13) Å^3	0.47 × 0.46 × 0.23 mm

Data collection

Rigaku Saturn724+ diffractometer	3759 independent reflections
Radiation source: Sealed tube	2737 reflections with I > 2σ(I)
Confocal monochromator	Rint = 0.021
Detector resolution: 28.5714 pixels mm^-1	θmax = 25.3°, θmin = 3.1°
profile data from ω–scans	h = −11→11
Absorption correction: multi-scan (NUMABS; Rigaku 1999)	k = −10→11
Tmin = 0.909, Tmax = 0.954	l = −13→15
5644 measured reflections

Refinement

Refinement on F^2	0 restraints
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F^2 > 2σ(F^2)] = 0.047	H-atom parameters constrained
wR(F^2) = 0.111	w = 1/[σ^2(Fo^2) + (0.0438P)^2 + 0.271P] where P = (Fo^2 + 2Fc^2)/3
S = 1.03	(Δ/σ)max < 0.001
3759 reflections	Δρmax = 0.23 e Å^−3
266 parameters	Δρmin = −0.26 e Å^−3

Special details

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.

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

	x	y	z	Uiso*/Ueq
Cl1	0.18349 (7)	0.60882 (6)	0.56379 (5)	0.0535 (2)
O27	0.4450 (2)	0.97619 (19)	0.78882 (17)	0.0728 (6)
O28	0.34218 (16)	0.74702 (16)	0.77727 (13)	0.0451 (4)
C20	0.1255 (2)	0.7722 (2)	0.61387 (17)	0.0375 (5)
C21	0.2059 (2)	0.8822 (2)	0.69885 (16)	0.0357 (5)
C22	0.1524 (3)	1.0101 (3)	0.72920 (18)	0.0487 (6)
H22	0.2047	1.0868	0.7842	0.058*
C23	0.0248 (3)	1.0276 (3)	0.68102 (19)	0.0533 (7)
H23	−0.0095	1.1138	0.7047	0.064*
C24	−0.0514 (3)	0.9175 (3)	0.5981 (2)	0.0542 (7)
H24	−0.1377	0.9289	0.5652	0.065*
C25	−0.0009 (3)	0.7906 (3)	0.56338 (19)	0.0498 (6)
H25	−0.0516	0.7168	0.5059	0.060*
C26	0.3432 (3)	0.8682 (2)	0.75872 (17)	0.0398 (5)
O7	1.02381 (18)	0.2539 (2)	0.99917 (13)	0.0586 (5)
O10	0.54164 (16)	0.26798 (16)	0.81780 (12)	0.0416 (4)
H10	0.5134	0.1793	0.7962	0.062*
N17	0.60162 (19)	0.71995 (18)	0.84805 (13)	0.0347 (4)
H17	0.5020	0.7134	0.8162	0.042*
C1	0.9828 (2)	0.3083 (2)	0.91759 (17)	0.0388 (5)
C2	1.0957 (2)	0.3841 (3)	0.87499 (18)	0.0448 (6)
H2	1.1932	0.3986	0.9028	0.054*
C3	1.0643 (2)	0.4392 (3)	0.79062 (19)	0.0467 (6)
H3	1.1407	0.4914	0.7618	0.056*
C4	0.9191 (2)	0.4169 (3)	0.74858 (18)	0.0421 (6)
H4	0.8992	0.4520	0.6904	0.050*
C5	0.8031 (2)	0.3428 (2)	0.79229 (16)	0.0320 (5)
C6	0.8359 (2)	0.2882 (2)	0.87754 (16)	0.0356 (5)
H6	0.7598	0.2381	0.9080	0.043*
C8	0.9107 (3)	0.1785 (4)	1.0477 (2)	0.0814 (10)
H8A	0.8580	0.0929	0.9955	0.122*
H8B	0.8432	0.2408	1.0751	0.122*
H8C	0.9540	0.1505	1.1054	0.122*
C9	0.6417 (2)	0.3177 (2)	0.74684 (16)	0.0324 (5)
C11	0.6219 (2)	0.2069 (2)	0.63600 (17)	0.0422 (6)
H11A	0.6982	0.2398	0.5924	0.051*
H11B	0.6365	0.1139	0.6448	0.051*
C12	0.4703 (3)	0.1842 (3)	0.5766 (2)	0.0536 (7)
H12A	0.4688	0.1204	0.5051	0.064*
H12B	0.3943	0.1376	0.6142	0.064*
C13	0.4369 (3)	0.3285 (3)	0.56868 (19)	0.0517 (7)
H13A	0.3374	0.3125	0.5354	0.062*
H13B	0.5060	0.3695	0.5238	0.062*
C14	0.4494 (2)	0.4356 (2)	0.67874 (17)	0.0426 (6)
H14A	0.3752	0.3976	0.7218	0.051*
H14B	0.4295	0.5274	0.6711	0.051*
C15	0.6030 (2)	0.4623 (2)	0.73608 (15)	0.0317 (5)
H15	0.6758	0.5041	0.6927	0.038*
C16	0.6174 (2)	0.5690 (2)	0.84660 (16)	0.0364 (5)
H16A	0.5425	0.5303	0.8889	0.044*
H16B	0.7137	0.5743	0.8813	0.044*
C18	0.6123 (3)	0.8113 (3)	0.96057 (18)	0.0555 (7)
H18A	0.5395	0.7656	0.9997	0.083*
H18B	0.5947	0.9059	0.9610	0.083*
H18C	0.7097	0.8212	0.9936	0.083*
C19	0.7097 (3)	0.7899 (3)	0.7845 (2)	0.0543 (7)
H19A	0.8086	0.7877	0.8085	0.082*
H19B	0.7003	0.8892	0.7937	0.082*
H19C	0.6903	0.7379	0.7100	0.082*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
Cl1	0.0658 (4)	0.0412 (4)	0.0514 (4)	0.0202 (3)	−0.0058 (3)	0.0027 (3)
O27	0.0604 (12)	0.0367 (10)	0.1158 (16)	−0.0075 (9)	−0.0366 (11)	0.0273 (10)
O28	0.0375 (9)	0.0325 (9)	0.0685 (10)	0.0069 (7)	−0.0082 (8)	0.0202 (8)
C20	0.0386 (12)	0.0337 (12)	0.0425 (12)	0.0091 (10)	0.0056 (10)	0.0130 (10)
C21	0.0379 (12)	0.0309 (12)	0.0414 (12)	0.0080 (10)	0.0051 (10)	0.0144 (9)
C22	0.0600 (16)	0.0366 (14)	0.0492 (14)	0.0186 (12)	−0.0044 (12)	0.0055 (11)
C23	0.0600 (17)	0.0492 (16)	0.0585 (15)	0.0304 (13)	0.0031 (13)	0.0141 (13)
C24	0.0431 (14)	0.0646 (18)	0.0630 (16)	0.0217 (13)	−0.0018 (12)	0.0240 (14)
C25	0.0467 (15)	0.0476 (15)	0.0530 (14)	0.0104 (12)	−0.0094 (12)	0.0106 (11)
C26	0.0409 (13)	0.0300 (13)	0.0476 (13)	0.0067 (11)	−0.0025 (11)	0.0097 (10)
O7	0.0397 (10)	0.0873 (14)	0.0591 (10)	0.0111 (9)	−0.0044 (8)	0.0401 (10)
O10	0.0354 (9)	0.0330 (9)	0.0565 (9)	0.0024 (7)	0.0060 (7)	0.0151 (7)
N17	0.0313 (10)	0.0282 (10)	0.0420 (10)	0.0059 (8)	−0.0037 (8)	0.0056 (8)
C1	0.0382 (13)	0.0417 (13)	0.0384 (12)	0.0121 (10)	0.0003 (10)	0.0115 (10)
C2	0.0267 (11)	0.0532 (15)	0.0534 (14)	0.0064 (11)	−0.0023 (10)	0.0138 (11)
C3	0.0298 (12)	0.0554 (16)	0.0603 (15)	0.0089 (11)	0.0103 (11)	0.0243 (12)
C4	0.0348 (13)	0.0485 (15)	0.0496 (13)	0.0139 (11)	0.0042 (11)	0.0210 (11)
C5	0.0294 (11)	0.0278 (11)	0.0396 (12)	0.0110 (9)	0.0023 (9)	0.0067 (9)
C6	0.0302 (11)	0.0356 (13)	0.0418 (12)	0.0076 (9)	0.0049 (10)	0.0109 (10)
C8	0.0576 (18)	0.117 (3)	0.085 (2)	0.0026 (18)	−0.0068 (16)	0.067 (2)
C9	0.0275 (11)	0.0291 (12)	0.0419 (12)	0.0063 (9)	0.0036 (9)	0.0113 (9)
C11	0.0432 (13)	0.0329 (13)	0.0483 (13)	0.0134 (10)	−0.0031 (11)	0.0035 (10)
C12	0.0529 (15)	0.0395 (14)	0.0580 (15)	0.0116 (12)	−0.0144 (13)	−0.0053 (11)
C13	0.0447 (14)	0.0484 (15)	0.0557 (15)	0.0150 (12)	−0.0189 (12)	0.0009 (12)
C14	0.0369 (13)	0.0363 (13)	0.0532 (14)	0.0147 (10)	−0.0067 (11)	0.0049 (10)
C15	0.0285 (11)	0.0296 (11)	0.0363 (11)	0.0072 (9)	−0.0017 (9)	0.0073 (9)
C16	0.0371 (12)	0.0302 (12)	0.0437 (12)	0.0109 (10)	−0.0008 (10)	0.0105 (9)
C18	0.0679 (17)	0.0428 (15)	0.0488 (14)	0.0193 (13)	−0.0081 (13)	−0.0047 (11)
C19	0.0479 (15)	0.0417 (15)	0.0737 (17)	0.0018 (12)	0.0085 (13)	0.0209 (13)

Geometric parameters (Å, º)

Cl1—C20	1.739 (2)	C5—C6	1.390 (3)
O27—C26	1.234 (3)	C5—C9	1.535 (3)
O28—C26	1.255 (3)	C6—H6	0.9300
C20—C21	1.396 (3)	C8—H8A	0.9600
C20—C25	1.383 (3)	C8—H8B	0.9600
C21—C22	1.387 (3)	C8—H8C	0.9600
C21—C26	1.512 (3)	C9—C11	1.538 (3)
C22—H22	0.9300	C9—C15	1.548 (3)
C22—C23	1.375 (3)	C11—H11A	0.9700
C23—H23	0.9300	C11—H11B	0.9700
C23—C24	1.368 (4)	C11—C12	1.526 (3)
C24—H24	0.9300	C12—H12A	0.9700
C24—C25	1.369 (3)	C12—H12B	0.9700
C25—H25	0.9300	C12—C13	1.515 (3)
O7—C1	1.370 (3)	C13—H13A	0.9700
O7—C8	1.411 (3)	C13—H13B	0.9700
O10—H10	0.8200	C13—C14	1.519 (3)
O10—C9	1.423 (2)	C14—H14A	0.9700
N17—H17	0.9800	C14—H14B	0.9700
N17—C16	1.493 (3)	C14—C15	1.525 (3)
N17—C18	1.487 (3)	C15—H15	0.9800
N17—C19	1.482 (3)	C15—C16	1.520 (3)
C1—C2	1.367 (3)	C16—H16A	0.9700
C1—C6	1.395 (3)	C16—H16B	0.9700
C2—H2	0.9300	C18—H18A	0.9600
C2—C3	1.379 (3)	C18—H18B	0.9600
C3—H3	0.9300	C18—H18C	0.9600
C3—C4	1.386 (3)	C19—H19A	0.9600
C4—H4	0.9300	C19—H19B	0.9600
C4—C5	1.386 (3)	C19—H19C	0.9600
C21—C20—Cl1	121.50 (17)	O10—C9—C11	111.22 (17)
C25—C20—Cl1	117.08 (18)	O10—C9—C15	105.91 (16)
C25—C20—C21	121.4 (2)	C5—C9—C11	108.63 (16)
C20—C21—C26	124.04 (19)	C5—C9—C15	110.75 (16)
C22—C21—C20	116.4 (2)	C11—C9—C15	109.63 (17)
C22—C21—C26	119.52 (19)	C9—C11—H11A	108.8
C21—C22—H22	118.8	C9—C11—H11B	108.8
C23—C22—C21	122.4 (2)	H11A—C11—H11B	107.7
C23—C22—H22	118.8	C12—C11—C9	113.94 (18)
C22—C23—H23	120.2	C12—C11—H11A	108.8
C24—C23—C22	119.6 (2)	C12—C11—H11B	108.8
C24—C23—H23	120.2	C11—C12—H12A	109.5
C23—C24—H24	119.9	C11—C12—H12B	109.5
C23—C24—C25	120.2 (2)	H12A—C12—H12B	108.1
C25—C24—H24	119.9	C13—C12—C11	110.77 (19)
C20—C25—H25	120.0	C13—C12—H12A	109.5
C24—C25—C20	120.0 (2)	C13—C12—H12B	109.5
C24—C25—H25	120.0	C12—C13—H13A	109.4
O27—C26—O28	124.8 (2)	C12—C13—H13B	109.4
O27—C26—C21	118.5 (2)	C12—C13—C14	111.1 (2)
O28—C26—C21	116.63 (19)	H13A—C13—H13B	108.0
C1—O7—C8	118.02 (18)	C14—C13—H13A	109.4
C9—O10—H10	109.5	C14—C13—H13B	109.4
C16—N17—H17	107.5	C13—C14—H14A	109.3
C18—N17—H17	107.5	C13—C14—H14B	109.3
C18—N17—C16	109.97 (17)	C13—C14—C15	111.71 (18)
C19—N17—H17	107.5	H14A—C14—H14B	107.9
C19—N17—C16	113.29 (17)	C15—C14—H14A	109.3
C19—N17—C18	110.81 (19)	C15—C14—H14B	109.3
O7—C1—C6	123.4 (2)	C9—C15—H15	108.0
C2—C1—O7	116.1 (2)	C14—C15—C9	111.10 (17)
C2—C1—C6	120.5 (2)	C14—C15—H15	108.0
C1—C2—H2	120.1	C16—C15—C9	109.16 (16)
C1—C2—C3	119.7 (2)	C16—C15—C14	112.43 (17)
C3—C2—H2	120.1	C16—C15—H15	108.0
C2—C3—H3	119.9	N17—C16—C15	115.42 (17)
C2—C3—C4	120.2 (2)	N17—C16—H16A	108.4
C4—C3—H3	119.9	N17—C16—H16B	108.4
C3—C4—H4	119.6	C15—C16—H16A	108.4
C3—C4—C5	120.8 (2)	C15—C16—H16B	108.4
C5—C4—H4	119.6	H16A—C16—H16B	107.5
C4—C5—C6	118.54 (19)	N17—C18—H18A	109.5
C4—C5—C9	121.37 (19)	N17—C18—H18B	109.5
C6—C5—C9	120.08 (19)	N17—C18—H18C	109.5
C1—C6—H6	119.9	H18A—C18—H18B	109.5
C5—C6—C1	120.2 (2)	H18A—C18—H18C	109.5
C5—C6—H6	119.9	H18B—C18—H18C	109.5
O7—C8—H8A	109.5	N17—C19—H19A	109.5
O7—C8—H8B	109.5	N17—C19—H19B	109.5
O7—C8—H8C	109.5	N17—C19—H19C	109.5
H8A—C8—H8B	109.5	H19A—C19—H19B	109.5
H8A—C8—H8C	109.5	H19A—C19—H19C	109.5
H8B—C8—H8C	109.5	H19B—C19—H19C	109.5
O10—C9—C5	110.70 (17)
Cl1—C20—C21—C22	177.46 (18)	C4—C5—C9—O10	−167.60 (18)
Cl1—C20—C21—C26	−3.5 (3)	C4—C5—C9—C11	70.0 (3)
Cl1—C20—C25—C24	−179.2 (2)	C4—C5—C9—C15	−50.4 (3)
C20—C21—C22—C23	1.8 (4)	C5—C9—C11—C12	−173.8 (2)
C20—C21—C26—O27	143.1 (2)	C5—C9—C15—C14	173.22 (17)
C20—C21—C26—O28	−39.3 (3)	C5—C9—C15—C16	−62.2 (2)
C21—C20—C25—C24	−1.4 (4)	C6—C1—C2—C3	−1.1 (3)
C21—C22—C23—C24	−1.8 (4)	C6—C5—C9—O10	13.8 (3)
C22—C21—C26—O27	−37.9 (3)	C6—C5—C9—C11	−108.6 (2)
C22—C21—C26—O28	139.7 (2)	C6—C5—C9—C15	130.95 (19)
C22—C23—C24—C25	0.1 (4)	C8—O7—C1—C2	178.2 (2)
C23—C24—C25—C20	1.5 (4)	C8—O7—C1—C6	−2.5 (3)
C25—C20—C21—C22	−0.2 (3)	C9—C5—C6—C1	178.68 (18)
C25—C20—C21—C26	178.8 (2)	C9—C11—C12—C13	53.9 (3)
C26—C21—C22—C23	−177.3 (2)	C9—C15—C16—N17	172.82 (16)
O7—C1—C2—C3	178.3 (2)	C11—C9—C15—C14	53.4 (2)
O7—C1—C6—C5	−178.0 (2)	C11—C9—C15—C16	177.90 (18)
O10—C9—C11—C12	64.1 (3)	C11—C12—C13—C14	−55.0 (3)
O10—C9—C15—C14	−66.7 (2)	C12—C13—C14—C15	57.8 (3)
O10—C9—C15—C16	57.8 (2)	C13—C14—C15—C9	−57.2 (3)
C1—C2—C3—C4	−0.5 (4)	C13—C14—C15—C16	−179.84 (19)
C2—C1—C6—C5	1.3 (3)	C14—C15—C16—N17	−63.4 (2)
C2—C3—C4—C5	1.8 (3)	C15—C9—C11—C12	−52.7 (3)
C3—C4—C5—C6	−1.6 (3)	C18—N17—C16—C15	177.93 (18)
C3—C4—C5—C9	179.80 (19)	C19—N17—C16—C15	−57.5 (2)
C4—C5—C6—C1	0.0 (3)

Hydrogen-bond geometry (Å, º)

Cg1 is the centroid of the C1–C6 ring.

D—H···A	D—H	H···A	D···A	D—H···A
O10—H10···O27^i	0.82	1.92	2.721 (3)	164
N17—H17···O28	0.98	1.66	2.619 (3)	164
C14—H14B···O28	0.97	2.50	3.305 (3)	140
C8—H8B···O28^ii	0.96	2.59	3.338 (4)	135
C18—H18A···O10^ii	0.96	2.58	3.428 (4)	148
C23—H23···Cg1^iii	0.93	2.66	3.546 (4)	160

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