2-Hydro­xy­benzoic acid salt of physostigmine

Physostigmine, C₁₅H₂₂N₃O₂, is the major alkaloid found in the seeds of Calabar beans. It was the first anticholinesterase used in the treatment of Alzheimer's disease and is still used in the treatment of glaucoma. The structure of its 2-hydroxy­benzoate salt, viz. 5-carbamoyl­oxy-1,2,3,3a,8,8a-hexa­hydro-1,3a,8-tri­methyl­pyrrolo­[2,3-b]­indol-1-ium benzoate, C₁₅H₂₂N₃O₂⁺·C₇H₅O₃^-, is reported.

Key indicators

• Single-crystal X-ray study
• T = 293 K
• Mean [sigma](C-C) = 0.004 Å
• R factor = 0.045
• wR factor = 0.124
• Data-to-parameter ratio = 7.6

checkCIF results

No syntax errors found

ADDSYM reports no extra symmetry


 Alert Level A:



THETM_01  Alert A The value of sine(theta_max)/wavelength is less than 0.550
          Calculated sin(theta_max)/wavelength =    0.5476

Author response: .This data was collected in the middle 80's and it was the best we could do at the time. It has been re-refined with newer programs to get cif files etc but since the crystals themselves are long gone we could not recollect the data.

 Alert Level C:



REFNR_01  Alert C Ratio of reflections to parameters is < 8 for a
          non-centrosymmetric structure, where ZMAX < 18
          sine(theta)/lambda                0.5476
          Proportion of unique data used    1.0000
          Ratio reflections to parameters   7.5567

STRVAL_01
         From the CIF: _refine_ls_abs_structure_Flack   -1.000
         From the CIF: _refine_ls_abs_structure_Flack_su    0.300
           Alert C Flack parameter is too small

General Notes



REFLT_03
         From the CIF: _diffrn_reflns_theta_max           57.59
         From the CIF: _reflns_number_total               2131
         Count of symmetry unique reflns         1716
         Completeness (_total/calc)            124.18%
         TEST3: Check Friedels for noncentro structure
         Estimate of Friedel pairs measured       415
         Fraction of Friedel pairs measured     0.242
         Are heavy atom types Z>Si present           no
          WARNING: CuKa measured Friedel data can be used to
                   determine absolute structure in a light-atom
                   study only if the Friedel fraction is large.


 1 Alert Level A = Potentially serious problem

 0 Alert Level B = Potential problem

 2 Alert Level C = Please check

---

Computing details

Data collection: XTAPE (Nicolet, 1983); cell refinement: XTAPE; data reduction: XDISK (Nicolet, 1983); program(s) used to solve structure: SHELXTL (Sheldrick, 1997); program(s) used to refine structure: SHELXTL (Sheldrick, 1997); molecular graphics: SHELXTL (Bruker, 2001); software used to prepare material for publication: SHELXTL (Bruker, 2001).

(I)

Crystal data

C15H22N3O2^+·C7H5O3^−	Dx = 1.266 Mg m^−3
Mr = 413.47	Cu Kα radiation, λ = 1.54178 Å
Orthorhombic, P212121	Cell parameters from 25 reflections
a = 9.970 (3) Å	θ = 20.8–38.3°
b = 10.945 (3) Å	µ = 0.74 mm^−1
c = 19.874 (3) Å	T = 293 K
V = 2168.8 (9) Å^3	Prism, colorless
Z = 4	0.40 × 0.25 × 0.20 mm
F(000) = 880

Data collection

Bruker P4 diffractometer	Rint = 0.044
Radiation source: normal-focus sealed tube	θmax = 57.6°, θmin = 4.5°
Graphite monochromator	h = −10→4
θ/2θ scans	k = 0→11
2333 measured reflections	l = 0→21
2131 independent reflections	3 standard reflections every 97 reflections
2094 reflections with I > 2σ(I)	intensity decay: none

Refinement

Refinement on F^2	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F^2 > 2σ(F^2)] = 0.045	H atoms treated by a mixture of independent and constrained refinement
wR(F^2) = 0.124	w = 1/[σ^2(Fo^2) + (0.1362P)^2 + 0.3533P] where P = (Fo^2 + 2Fc^2)/3
S = 0.80	(Δ/σ)max = 0.026
2131 reflections	Δρmax = 0.16 e Å^−3
282 parameters	Δρmin = −0.14 e Å^−3
0 restraints	Absolute structure: Flack (1983), 415 Friedel pairs [CHECK]
Primary atom site location: structure-invariant direct methods	Absolute structure parameter: −1.0 (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.

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 > σ(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.

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

	x	y	z	Uiso*/Ueq
N1	0.8598 (2)	0.04951 (17)	0.17821 (10)	0.0508 (6)
H1	0.870 (3)	0.091 (3)	0.2181 (15)	0.061*
C1A	0.8241 (4)	−0.0793 (2)	0.19414 (14)	0.0686 (8)
H1AA	0.8908	−0.1136	0.2234	0.103*
H1AB	0.8201	−0.1259	0.1533	0.103*
H1AC	0.7383	−0.0815	0.2160	0.103*
C2	0.9952 (3)	0.0650 (2)	0.14883 (13)	0.0547 (6)
H2A	1.0085	0.0114	0.1105	0.066*
H2B	1.0647	0.0497	0.1819	0.066*
C3	0.9932 (3)	0.1971 (2)	0.12773 (13)	0.0564 (7)
H3A	1.0627	0.2135	0.0948	0.068*
H3B	1.0064	0.2504	0.1662	0.068*
C3A	0.8539 (3)	0.2153 (2)	0.09722 (11)	0.0455 (6)
C3B	0.8004 (4)	0.3456 (2)	0.10724 (15)	0.0642 (8)
H3BA	0.8591	0.4026	0.0853	0.096*
H3BB	0.7965	0.3638	0.1545	0.096*
H3BC	0.7122	0.3519	0.0882	0.096*
C4	0.9119 (3)	0.2217 (2)	−0.03126 (12)	0.0509 (6)
H4A	0.9727	0.2856	−0.0270	0.061*
C4A	0.8470 (3)	0.1753 (2)	0.02398 (11)	0.0444 (6)
C5	0.8844 (3)	0.1707 (3)	−0.09369 (13)	0.0542 (6)
C6	0.7954 (3)	0.0762 (3)	−0.10042 (13)	0.0600 (7)
H6A	0.7783	0.0438	−0.1428	0.072*
C7	0.7309 (3)	0.0285 (2)	−0.04515 (13)	0.0594 (7)
H7A	0.6702	−0.0355	−0.0498	0.071*
C7A	0.7583 (3)	0.0778 (2)	0.01768 (12)	0.0455 (6)
N8	0.7101 (2)	0.04122 (18)	0.08027 (10)	0.0543 (6)
C8A	0.7630 (3)	0.1176 (2)	0.13200 (11)	0.0463 (6)
H8AA	0.6908	0.1564	0.1578	0.056*
C8B	0.5857 (3)	−0.0262 (3)	0.08787 (17)	0.0700 (8)
H8BA	0.6032	−0.1121	0.0838	0.105*
H8BB	0.5237	−0.0015	0.0535	0.105*
H8BC	0.5478	−0.0095	0.1313	0.105*
O9	0.95513 (19)	0.2130 (2)	−0.15066 (9)	0.0669 (6)
C10	0.8872 (3)	0.2899 (3)	−0.19249 (14)	0.0615 (7)
O10	0.7801 (3)	0.3288 (3)	−0.17988 (16)	0.1169 (12)
N11	0.9591 (3)	0.3153 (3)	−0.24678 (13)	0.0779 (9)
H11	1.024 (5)	0.272 (4)	−0.254 (2)	0.093*
C12	0.9118 (5)	0.3978 (6)	−0.2974 (2)	0.134 (2)
H12A	0.9530	0.3782	−0.3397	0.201*
H12B	0.9344	0.4800	−0.2850	0.201*
H12C	0.8161	0.3904	−0.3014	0.201*
C1'	0.8551 (3)	0.2758 (2)	0.38573 (11)	0.0521 (6)
C1'A	0.8258 (4)	0.2158 (3)	0.31986 (14)	0.0661 (8)
O1'A	0.7269 (3)	0.2424 (3)	0.28750 (12)	0.1067 (9)
O1'B	0.9098 (3)	0.1358 (2)	0.30100 (11)	0.0908 (8)
C2'	0.9701 (3)	0.2498 (2)	0.42212 (14)	0.0615 (7)
O2'	1.0589 (3)	0.1661 (2)	0.40132 (15)	0.0932 (8)
H2'	1.020 (5)	0.141 (4)	0.355 (2)	0.112*
C3'	0.9941 (5)	0.3125 (3)	0.48298 (15)	0.0794 (11)
H3'A	1.0708	0.2964	0.5081	0.095*
C4'	0.9027 (5)	0.3972 (3)	0.50452 (15)	0.0927 (13)
H4'A	0.9179	0.4377	0.5449	0.111*
C5'	0.7888 (5)	0.4243 (4)	0.4681 (2)	0.0953 (12)
H5'A	0.7287	0.4830	0.4834	0.114*
C6'	0.7663 (3)	0.3640 (3)	0.40999 (16)	0.0760 (9)
H6'A	0.6894	0.3817	0.3854	0.091*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
N1	0.0660 (14)	0.0457 (11)	0.0408 (10)	−0.0018 (11)	0.0011 (11)	−0.0048 (9)
C1A	0.090 (2)	0.0524 (13)	0.0635 (15)	−0.0066 (17)	−0.0041 (17)	0.0128 (13)
C2	0.0506 (15)	0.0599 (14)	0.0535 (13)	0.0053 (13)	−0.0064 (12)	−0.0011 (11)
C3	0.0556 (16)	0.0608 (14)	0.0527 (13)	−0.0122 (14)	−0.0059 (12)	−0.0029 (12)
C3A	0.0470 (14)	0.0396 (11)	0.0499 (12)	−0.0063 (11)	0.0019 (11)	−0.0053 (10)
C3B	0.078 (2)	0.0447 (13)	0.0702 (16)	−0.0006 (14)	−0.0013 (16)	−0.0052 (12)
C4	0.0454 (13)	0.0521 (13)	0.0553 (14)	−0.0033 (12)	0.0001 (12)	0.0031 (11)
C4A	0.0435 (13)	0.0418 (11)	0.0480 (12)	−0.0002 (11)	−0.0040 (11)	−0.0008 (10)
C5	0.0491 (14)	0.0646 (15)	0.0487 (13)	0.0056 (13)	0.0014 (12)	0.0034 (12)
C6	0.0692 (18)	0.0639 (15)	0.0469 (14)	0.0041 (15)	−0.0086 (13)	−0.0053 (12)
C7	0.0674 (18)	0.0525 (14)	0.0582 (15)	−0.0079 (14)	−0.0151 (15)	−0.0044 (11)
C7A	0.0453 (13)	0.0416 (11)	0.0496 (12)	−0.0027 (11)	−0.0064 (12)	−0.0005 (10)
N8	0.0539 (13)	0.0563 (11)	0.0525 (11)	−0.0196 (11)	−0.0034 (11)	0.0012 (10)
C8A	0.0488 (14)	0.0431 (11)	0.0471 (12)	−0.0005 (12)	0.0048 (11)	−0.0026 (10)
C8B	0.0628 (17)	0.0675 (16)	0.0796 (18)	−0.0213 (16)	−0.0001 (16)	0.0091 (16)
O9	0.0547 (11)	0.0959 (14)	0.0501 (9)	0.0134 (11)	0.0089 (9)	0.0117 (10)
C10	0.0481 (16)	0.0775 (18)	0.0587 (15)	−0.0002 (15)	0.0018 (13)	0.0125 (14)
O10	0.0619 (15)	0.146 (2)	0.143 (2)	0.0415 (16)	0.0384 (16)	0.080 (2)
N11	0.0568 (16)	0.117 (2)	0.0598 (14)	0.0002 (17)	0.0063 (14)	0.0250 (15)
C12	0.101 (3)	0.194 (5)	0.108 (3)	−0.015 (4)	0.000 (3)	0.090 (4)
C1'	0.0577 (15)	0.0556 (13)	0.0432 (11)	−0.0176 (13)	0.0033 (13)	0.0010 (10)
C1'A	0.0745 (19)	0.0710 (17)	0.0528 (14)	−0.0203 (18)	−0.0020 (16)	−0.0022 (14)
O1'A	0.0921 (18)	0.141 (2)	0.0867 (15)	−0.016 (2)	−0.0395 (16)	−0.0162 (16)
O1'B	0.121 (2)	0.0895 (14)	0.0622 (12)	−0.0014 (17)	−0.0044 (14)	−0.0281 (12)
C2'	0.0823 (19)	0.0455 (13)	0.0566 (13)	−0.0120 (16)	−0.0104 (16)	0.0097 (11)
O2'	0.104 (2)	0.0659 (13)	0.1100 (18)	0.0165 (13)	−0.0335 (16)	−0.0025 (12)
C3'	0.114 (3)	0.0658 (17)	0.0582 (15)	−0.031 (2)	−0.032 (2)	0.0168 (14)
C4'	0.152 (4)	0.082 (2)	0.0447 (15)	−0.023 (3)	0.009 (2)	−0.0169 (15)
C5'	0.089 (3)	0.114 (3)	0.083 (2)	−0.009 (2)	0.025 (2)	−0.033 (2)
C6'	0.0573 (17)	0.095 (2)	0.0761 (18)	−0.0132 (18)	0.0176 (17)	−0.0185 (18)

Geometric parameters (Å, º)

N1—C2	1.481 (4)	N8—C8A	1.426 (3)
N1—C1A	1.488 (3)	N8—C8B	1.452 (4)
N1—C8A	1.526 (3)	C8A—H8AA	0.9800
N1—H1	0.92 (3)	C8B—H8BA	0.9600
C1A—H1AA	0.9600	C8B—H8BB	0.9600
C1A—H1AB	0.9600	C8B—H8BC	0.9600
C1A—H1AC	0.9600	O9—C10	1.364 (4)
C2—C3	1.506 (4)	C10—O10	1.176 (4)
C2—H2A	0.9700	C10—N11	1.325 (4)
C2—H2B	0.9700	N11—C12	1.431 (5)
C3—C3A	1.529 (4)	N11—H11	0.82 (5)
C3—H3A	0.9700	C12—H12A	0.9600
C3—H3B	0.9700	C12—H12B	0.9600
C3A—C4A	1.522 (3)	C12—H12C	0.9600
C3A—C3B	1.535 (3)	C1'—C2'	1.386 (4)
C3A—C8A	1.564 (3)	C1'—C6'	1.395 (4)
C3B—H3BA	0.9600	C1'—C1'A	1.494 (4)
C3B—H3BB	0.9600	C1'A—O1'A	1.213 (4)
C3B—H3BC	0.9600	C1'A—O1'B	1.268 (4)
C4—C4A	1.371 (4)	C2'—O2'	1.339 (4)
C4—C5	1.388 (4)	C2'—C3'	1.411 (4)
C4—H4A	0.9300	O2'—H2'	1.03 (5)
C4A—C7A	1.392 (3)	C3'—C4'	1.369 (6)
C5—C6	1.370 (4)	C3'—H3'A	0.9300
C5—O9	1.412 (3)	C4'—C5'	1.378 (6)
C6—C7	1.375 (4)	C4'—H4'A	0.9300
C6—H6A	0.9300	C5'—C6'	1.350 (5)
C7—C7A	1.387 (3)	C5'—H5'A	0.9300
C7—H7A	0.9300	C6'—H6'A	0.9300
C7A—N8	1.392 (3)
C2—N1—C1A	114.2 (2)	C7—C7A—N8	128.7 (2)
C2—N1—C8A	106.46 (18)	C4A—C7A—N8	111.06 (19)
C1A—N1—C8A	116.0 (2)	C7A—N8—C8A	110.39 (18)
C2—N1—H1	100 (2)	C7A—N8—C8B	122.3 (2)
C1A—N1—H1	108.3 (18)	C8A—N8—C8B	122.6 (2)
C8A—N1—H1	110.4 (19)	N8—C8A—N1	112.42 (18)
N1—C1A—H1AA	109.5	N8—C8A—C3A	107.25 (18)
N1—C1A—H1AB	109.5	N1—C8A—C3A	103.5 (2)
H1AA—C1A—H1AB	109.5	N8—C8A—H8AA	111.1
N1—C1A—H1AC	109.5	N1—C8A—H8AA	111.1
H1AA—C1A—H1AC	109.5	C3A—C8A—H8AA	111.1
H1AB—C1A—H1AC	109.5	N8—C8B—H8BA	109.5
N1—C2—C3	102.0 (2)	N8—C8B—H8BB	109.5
N1—C2—H2A	111.4	H8BA—C8B—H8BB	109.5
C3—C2—H2A	111.4	N8—C8B—H8BC	109.5
N1—C2—H2B	111.4	H8BA—C8B—H8BC	109.5
C3—C2—H2B	111.4	H8BB—C8B—H8BC	109.5
H2A—C2—H2B	109.2	C10—O9—C5	116.3 (2)
C2—C3—C3A	104.3 (2)	O10—C10—N11	126.1 (3)
C2—C3—H3A	110.9	O10—C10—O9	123.0 (3)
C3A—C3—H3A	110.9	N11—C10—O9	110.9 (3)
C2—C3—H3B	110.9	C10—N11—C12	121.7 (3)
C3A—C3—H3B	110.9	C10—N11—H11	117 (3)
H3A—C3—H3B	108.9	C12—N11—H11	120 (3)
C4A—C3A—C3	112.5 (2)	N11—C12—H12A	109.5
C4A—C3A—C3B	112.1 (2)	N11—C12—H12B	109.5
C3—C3A—C3B	112.7 (2)	H12A—C12—H12B	109.5
C4A—C3A—C8A	101.52 (18)	N11—C12—H12C	109.5
C3—C3A—C8A	105.2 (2)	H12A—C12—H12C	109.5
C3B—C3A—C8A	112.1 (2)	H12B—C12—H12C	109.5
C3A—C3B—H3BA	109.5	C2'—C1'—C6'	119.1 (2)
C3A—C3B—H3BB	109.5	C2'—C1'—C1'A	121.9 (3)
H3BA—C3B—H3BB	109.5	C6'—C1'—C1'A	118.9 (3)
C3A—C3B—H3BC	109.5	O1'A—C1'A—O1'B	123.1 (3)
H3BA—C3B—H3BC	109.5	O1'A—C1'A—C1'	121.2 (3)
H3BB—C3B—H3BC	109.5	O1'B—C1'A—C1'	115.7 (3)
C4A—C4—C5	118.3 (2)	O2'—C2'—C1'	121.8 (3)
C4A—C4—H4A	120.8	O2'—C2'—C3'	119.1 (3)
C5—C4—H4A	120.8	C1'—C2'—C3'	119.2 (3)
C4—C4A—C7A	120.8 (2)	C2'—O2'—H2'	102 (3)
C4—C4A—C3A	129.6 (2)	C4'—C3'—C2'	119.0 (3)
C7A—C4A—C3A	109.6 (2)	C4'—C3'—H3'A	120.5
C6—C5—C4	121.2 (2)	C2'—C3'—H3'A	120.5
C6—C5—O9	119.5 (2)	C3'—C4'—C5'	122.0 (3)
C4—C5—O9	119.1 (2)	C3'—C4'—H4'A	119.0
C5—C6—C7	120.7 (2)	C5'—C4'—H4'A	119.0
C5—C6—H6A	119.6	C6'—C5'—C4'	118.7 (4)
C7—C6—H6A	119.6	C6'—C5'—H5'A	120.6
C6—C7—C7A	118.7 (3)	C4'—C5'—H5'A	120.6
C6—C7—H7A	120.7	C5'—C6'—C1'	121.9 (4)
C7A—C7—H7A	120.7	C5'—C6'—H6'A	119.0
C7—C7A—C4A	120.3 (2)	C1'—C6'—H6'A	119.0
C1A—N1—C2—C3	170.8 (2)	C8B—N8—C8A—C3A	−155.1 (2)
C8A—N1—C2—C3	41.4 (2)	C2—N1—C8A—N8	90.7 (2)
N1—C2—C3—C3A	−41.6 (2)	C1A—N1—C8A—N8	−37.6 (3)
C2—C3—C3A—C4A	−83.3 (2)	C2—N1—C8A—C3A	−24.6 (2)
C2—C3—C3A—C3B	148.8 (2)	C1A—N1—C8A—C3A	−153.0 (2)
C2—C3—C3A—C8A	26.4 (3)	C4A—C3A—C8A—N8	−3.1 (3)
C5—C4—C4A—C7A	1.5 (4)	C3—C3A—C8A—N8	−120.5 (2)
C5—C4—C4A—C3A	−177.8 (3)	C3B—C3A—C8A—N8	116.7 (2)
C3—C3A—C4A—C4	−64.4 (3)	C4A—C3A—C8A—N1	116.0 (2)
C3B—C3A—C4A—C4	63.8 (4)	C3—C3A—C8A—N1	−1.5 (2)
C8A—C3A—C4A—C4	−176.4 (3)	C3B—C3A—C8A—N1	−124.3 (2)
C3—C3A—C4A—C7A	116.2 (2)	C6—C5—O9—C10	80.1 (3)
C3B—C3A—C4A—C7A	−115.6 (2)	C4—C5—O9—C10	−103.2 (3)
C8A—C3A—C4A—C7A	4.2 (3)	C5—O9—C10—O10	6.6 (5)
C4A—C4—C5—C6	−0.2 (4)	C5—O9—C10—N11	−174.8 (3)
C4A—C4—C5—O9	−176.8 (2)	O10—C10—N11—C12	0.8 (6)
C4—C5—C6—C7	−0.4 (4)	O9—C10—N11—C12	−177.7 (4)
O9—C5—C6—C7	176.2 (3)	C2'—C1'—C1'A—O1'A	−177.6 (3)
C5—C6—C7—C7A	−0.2 (4)	C6'—C1'—C1'A—O1'A	0.0 (4)
C6—C7—C7A—C4A	1.5 (4)	C2'—C1'—C1'A—O1'B	3.1 (4)
C6—C7—C7A—N8	−176.9 (3)	C6'—C1'—C1'A—O1'B	−179.4 (3)
C4—C4A—C7A—C7	−2.1 (4)	C6'—C1'—C2'—O2'	180.0 (3)
C3A—C4A—C7A—C7	177.3 (2)	C1'A—C1'—C2'—O2'	−2.5 (4)
C4—C4A—C7A—N8	176.5 (2)	C6'—C1'—C2'—C3'	0.4 (4)
C3A—C4A—C7A—N8	−4.0 (3)	C1'A—C1'—C2'—C3'	178.0 (2)
C7—C7A—N8—C8A	−179.6 (3)	O2'—C2'—C3'—C4'	−179.4 (3)
C4A—C7A—N8—C8A	1.9 (3)	C1'—C2'—C3'—C4'	0.1 (4)
C7—C7A—N8—C8B	−23.5 (4)	C2'—C3'—C4'—C5'	−0.8 (5)
C4A—C7A—N8—C8B	158.0 (2)	C3'—C4'—C5'—C6'	0.9 (6)
C7A—N8—C8A—N1	−112.2 (2)	C4'—C5'—C6'—C1'	−0.3 (6)
C8B—N8—C8A—N1	91.8 (3)	C2'—C1'—C6'—C5'	−0.4 (5)
C7A—N8—C8A—C3A	0.9 (3)	C1'A—C1'—C6'—C5'	−178.0 (3)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1···O1′B	0.92 (3)	1.76 (3)	2.664 (3)	165 (3)
O2′—H2′···O1′B	1.03 (5)	1.54 (5)	2.509 (4)	154 (4)
N11—H11···O1′A^i	0.82 (5)	2.13 (5)	2.860 (4)	149 (4)

Symmetry code: (i) x+1/2, −y+1/2, −z.