4,4′-Dimeth­oxy-2,2′-[1,2-phenyl­ene­bis(nitrilo­methyl­idyne)]diphenol

The title compound, C₂₂H₂₀N₂O₄, was synthesized by the reaction of o-phenyl­enediamine with 5-methoxy­salicyl­aldehyde, as an extension of our investigations of Schiff base ligands and complexes. The central ring makes dihedral angles of 36.35 (5) and 17.81 (5)° with the two phenol rings. Each meth­oxy group is coplanar with the attached phenol ring. There are two O—H...N intra­molecular hydrogen bonds involving the two hydr­oxy groups, which generate S(6) ring motifs. In the crystal structure, the mol­ecules are arranged into chains along the c axis. These chains form mol­ecular sheets parallel to the ac plane. The crystal is stabilized by intra­molecular O—H...N hydrogen bonds and C—H...π inter­actions.

Key indicators

• Single-crystal X-ray study
• T = 100 K
• Mean [sigma](C-C) = 0.002 Å
• R factor = 0.053
• wR factor = 0.154
• Data-to-parameter ratio = 29.4

checkCIF/PLATON results

No syntax errors found



Alert level C
PLAT066_ALERT_1_C Predicted and Reported Transmissions Identical .          ?
PLAT153_ALERT_1_C The su's on the Cell Axes   are Equal (x 100000)         30 Ang.
PLAT222_ALERT_3_C Large Non-Solvent    H     Ueq(max)/Ueq(min) ...       3.95 Ratio
PLAT720_ALERT_4_C Number of Unusual/Non-Standard Label(s) ........          2

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

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

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S1. Comment

Schiff base compounds have received much attention because of their potential applications. Some of these compounds exhibit various pharmacological activities, such as anticancer (Dao et al., 2000), anti-HIV (Sriram et al., 2006), antibacterial and antifungal (Karthikeyan et al., 2006) properties. In addition, some of them may be used as analytical reagents for the determination of trace elements (Eltayeb & Ahmed, 2005a,b). We have previously reported the crystal structures of Schiff base ligands which are 2,2'-[1,2-phenylenebis(nitrilomethylidyne)]bis(5-methylphenol) (Eltayeb et al., 2007a), 6,6'-dimethyl-2,2'-[1,2-phenylenebis(nitrilomethylidyne)]diphenol (Eltayeb et al., 2007b) and 5,5'-dimethoxy-2,2'-[1,2-phenylenebis(nitrilomethylidyne)]diphenol (Eltayeb et al., 2007). As an extension of our investigations of Schiff base ligands and complexes, the title compound, (I), was synthesized by the reaction of o-phenylenediamine with 5-methoxysalicylaldehyde, and its crystal structure is reported here.

The structure of the title compound is not planar. The orientations of the C1–C6 and C15–C20 benzene rings respect to the o-phenylenediamine unit are indicated by the dihedral angles of 36.35 (5) and 17.81 (5)°, respectively. The C1–C6 and C15–C20 benzene rings makes the dihedral angle of 43.94 (5)°. The two methoxy groups are planarly attached to the C1–C6 and C15–C20 benzene rings. The C8/N1/C7/C6 unit is not planar as indicated by the torsion angles C8/N1/C7/C6 = -171.09 (8)° while the C13/N2/C14/C15 unit is planarly attached with the torsion angle of 178.91 (8)°. The orientations of these units with respect to the o-phenylenediamine ring are shown by the torsion angles C7/N1/C8/C9 = 31.92 (13)° and C14/N2/C13/C12 = -22.97 (14)°.

The two intramolecular hydrogen bonds, O1—H1O1···N1 and O3—H1O3···N2 generate S(6) ring motifs (Bernstein et al., 1995). Bond lengths and angles in (I) are in normal ranges (Allen et al., 1987) and comparable to those in related structures (Eltayeb et al., 2007; Eltayeb et al., 2007a,b).

In the crystal, the molecules are arranged into chains along the c axis. These chains form molecular sheets parallel to the ac plane (Fig. 2). The crystal is stabilized by O—H···N intramolecular hydrogen bonds (Table 1) and further stabilized by C—H···π interactions (Table 1); Cg₁ and Cg₂ are the centroids of C8–C13 and C15–C20 benzene rings, respectively.

Related literature

For related literature on values of bond lengths and angles, see: Allen et al. (1987). For related literature on hydrogen-bond motifs, see: Bernstein et al. (1995). For related structures, see, for example: Eltayeb, Teoh, Chantrapromma et al. (2007); Eltayeb, Teoh, Teh et al. (2007a,b). For related literature on pharmacological activities and applications, see, for example: Dao et al. (2000); Karthikeyan et al. (2006); Sriram et al. (2006); Eltayeb & Ahmed (2005a,b).

S2. Experimental

The title compound was synthesized by adding 5-methoxysalicylaldehyde (0.4 ml, 4 mmol) into a solution of o-phenylenediamine (0.216 g, 2 mmol) in ethanol 95% (20 ml). The mixture was refluxed with stirring for half an hour. The resultant red solution was filtered. Red plate-shaped single crystals of (I) suitable for X-ray structure determination were formed after two days of slow evaporation of the solvent at room temperature.

S3. Refinement

All H atoms were positioned geometrically and allowed to ride on their parent atoms, with O—H distances of 0.86–0.90 Å and C—H distances in the range 0.93–0.96 Å. The U_iso values were constrained to be 1.5U_eq of the carrier atom for methyl H atoms and 1.2U_eq for the remaining H atoms. A rotating group model was used for the methyl groups.

Computing details

Data collection: APEX2 (Bruker, 2005); cell refinement: APEX2; data reduction: SAINT (Bruker, 2005); program(s) used to solve structure: SHELXTL (Sheldrick, 1998); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL and PLATON (Spek, 2003).

Figures

	Fig. 1. The molecular structure of (I), showing 50% probability displacement ellipsoids and the atomic numbering. Hydrogen bonds were drawn as dash lines.
	Fig. 2. The crystal packing of (I), viewed along the b axis. Hydrogen bonds were drawn as dash lines.

4,4'-Dimethoxy-2,2'-[1,2-phenylenebis(nitrilomethylidyne)]diphenol

Crystal data

C22H20N2O4	F(000) = 792
Mr = 376.40	Dx = 1.357 Mg m^−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 8095 reflections
a = 11.6772 (3) Å	θ = 2.3–35.0°
b = 13.8721 (3) Å	µ = 0.09 mm^−1
c = 13.1182 (3) Å	T = 100 K
β = 119.875 (2)°	Plate, red
V = 1842.60 (8) Å^3	0.57 × 0.47 × 0.12 mm
Z = 4

Data collection

Bruker SMART APEX II CCD area-detector diffractometer	8095 independent reflections
Radiation source: fine-focus sealed tube	6228 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.049
Detector resolution: 8.33 pixels mm^-1	θmax = 35.0°, θmin = 2.3°
ω scans	h = −18→18
Absorption correction: multi-scan (SADABS; Bruker, 2005)	k = −22→22
Tmin = 0.948, Tmax = 0.989	l = −21→21
36710 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)] = 0.053	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.154	H-atom parameters constrained
S = 1.04	w = 1/[σ^2(Fo^2) + (0.0831P)^2 + 0.3111P] where P = (Fo^2 + 2Fc^2)/3
8095 reflections	(Δ/σ)max = 0.001
275 parameters	Δρmax = 0.41 e Å^−3
0 restraints	Δρmin = −0.33 e Å^−3

Special details

Experimental. The low-temparture data was collected with the Oxford Cyrosystem Cobra low-temperature attachment.

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
O1	0.83325 (7)	0.46826 (6)	0.48148 (6)	0.02043 (15)
H1O1	0.7502	0.4544	0.4461	0.062 (6)*
O2	1.06862 (7)	0.28976 (6)	0.91533 (7)	0.02480 (16)
O3	0.72475 (7)	0.41856 (6)	0.21130 (6)	0.02213 (15)
H1O3	0.6644	0.4180	0.2348	0.075 (7)*
O4	0.48112 (7)	0.34127 (6)	−0.26517 (6)	0.02223 (15)
N1	0.60911 (8)	0.39635 (6)	0.43686 (7)	0.01623 (15)
N2	0.49232 (8)	0.40442 (6)	0.19622 (7)	0.01599 (15)
C1	0.88570 (9)	0.42265 (7)	0.58656 (8)	0.01575 (16)
C2	1.01832 (9)	0.43830 (7)	0.66858 (8)	0.01768 (17)
H2A	1.0690	0.4789	0.6503	0.024 (4)*
C3	1.07443 (9)	0.39357 (7)	0.77689 (8)	0.01846 (17)
H3A	1.1626	0.4052	0.8317	0.028 (4)*
C4	1.00057 (9)	0.33070 (7)	0.80566 (8)	0.01765 (17)
C5	0.86873 (9)	0.31521 (7)	0.72544 (8)	0.01713 (16)
H5A	0.8192	0.2738	0.7441	0.025 (4)*
C6	0.80918 (9)	0.36209 (7)	0.61532 (8)	0.01528 (16)
C7	0.66841 (9)	0.35170 (7)	0.53648 (8)	0.01638 (16)
H7A	0.6197	0.3121	0.5580	0.019 (3)*
C8	0.47016 (9)	0.39602 (7)	0.36932 (8)	0.01505 (15)
C9	0.39089 (10)	0.39297 (7)	0.42200 (9)	0.01845 (17)
H9A	0.4305	0.3887	0.5033	0.032 (4)*
C10	0.25443 (10)	0.39636 (8)	0.35414 (9)	0.02039 (18)
H10A	0.2029	0.3916	0.3897	0.034 (4)*
C11	0.19468 (10)	0.40685 (8)	0.23291 (9)	0.02124 (19)
H11A	0.1032	0.4106	0.1876	0.029 (4)*
C12	0.27157 (9)	0.41177 (8)	0.17945 (9)	0.01916 (18)
H12A	0.2312	0.4200	0.0985	0.027 (4)*
C13	0.40965 (9)	0.40438 (7)	0.24637 (8)	0.01541 (16)
C14	0.44488 (9)	0.37959 (7)	0.08798 (8)	0.01615 (16)
H14A	0.3568	0.3609	0.0448	0.028 (4)*
C15	0.52455 (9)	0.37990 (7)	0.03136 (8)	0.01512 (15)
C16	0.46282 (9)	0.35957 (7)	−0.08930 (8)	0.01622 (16)
H16A	0.3727	0.3469	−0.1309	0.023 (3)*
C17	0.53497 (9)	0.35827 (7)	−0.14717 (8)	0.01730 (16)
C18	0.67094 (10)	0.37513 (8)	−0.08346 (9)	0.01983 (18)
H18A	0.7201	0.3728	−0.1215	0.038 (4)*
C19	0.73312 (10)	0.39529 (7)	0.03560 (9)	0.01973 (18)
H19A	0.8236	0.4066	0.0768	0.034 (4)*
C20	0.66080 (9)	0.39875 (7)	0.09450 (8)	0.01706 (16)
C21	0.99719 (12)	0.22443 (10)	0.94684 (11)	0.0321 (3)
H21A	1.0553	0.1983	1.0234	0.047 (5)*
H21B	0.9623	0.1731	0.8904	0.041 (5)*
H21C	0.9259	0.2580	0.9480	0.038 (4)*
C22	0.34072 (10)	0.33517 (8)	−0.33058 (9)	0.02211 (19)
H22A	0.3125	0.3243	−0.4120	0.034 (4)*
H22B	0.3033	0.3943	−0.3226	0.038 (4)*
H22C	0.3117	0.2827	−0.3013	0.022 (3)*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
O1	0.0168 (3)	0.0278 (4)	0.0151 (3)	−0.0011 (3)	0.0067 (2)	0.0054 (3)
O2	0.0181 (3)	0.0329 (4)	0.0166 (3)	−0.0015 (3)	0.0035 (3)	0.0090 (3)
O3	0.0155 (3)	0.0301 (4)	0.0173 (3)	−0.0036 (3)	0.0055 (3)	−0.0050 (3)
O4	0.0211 (3)	0.0304 (4)	0.0165 (3)	0.0008 (3)	0.0104 (3)	−0.0006 (3)
N1	0.0136 (3)	0.0192 (3)	0.0134 (3)	−0.0008 (3)	0.0049 (3)	−0.0004 (3)
N2	0.0141 (3)	0.0180 (3)	0.0152 (3)	0.0007 (3)	0.0068 (3)	0.0005 (3)
C1	0.0157 (4)	0.0182 (4)	0.0137 (3)	0.0000 (3)	0.0076 (3)	0.0007 (3)
C2	0.0146 (4)	0.0206 (4)	0.0178 (4)	−0.0021 (3)	0.0081 (3)	0.0003 (3)
C3	0.0131 (4)	0.0227 (4)	0.0169 (4)	−0.0012 (3)	0.0054 (3)	0.0002 (3)
C4	0.0158 (4)	0.0210 (4)	0.0137 (4)	0.0002 (3)	0.0054 (3)	0.0021 (3)
C5	0.0158 (4)	0.0181 (4)	0.0154 (4)	−0.0018 (3)	0.0062 (3)	0.0018 (3)
C6	0.0134 (4)	0.0165 (4)	0.0139 (3)	−0.0014 (3)	0.0052 (3)	−0.0002 (3)
C7	0.0154 (4)	0.0161 (4)	0.0156 (4)	−0.0021 (3)	0.0062 (3)	0.0000 (3)
C8	0.0131 (4)	0.0156 (4)	0.0149 (4)	−0.0001 (3)	0.0058 (3)	0.0003 (3)
C9	0.0180 (4)	0.0216 (4)	0.0165 (4)	0.0007 (3)	0.0092 (3)	0.0008 (3)
C10	0.0173 (4)	0.0242 (4)	0.0219 (4)	0.0017 (3)	0.0114 (4)	0.0008 (3)
C11	0.0137 (4)	0.0270 (5)	0.0219 (4)	0.0020 (3)	0.0079 (3)	−0.0002 (3)
C12	0.0142 (4)	0.0250 (4)	0.0158 (4)	0.0022 (3)	0.0055 (3)	0.0001 (3)
C13	0.0128 (4)	0.0175 (4)	0.0146 (4)	0.0003 (3)	0.0059 (3)	−0.0001 (3)
C14	0.0139 (4)	0.0184 (4)	0.0150 (4)	0.0003 (3)	0.0064 (3)	0.0005 (3)
C15	0.0136 (4)	0.0156 (4)	0.0153 (4)	0.0005 (3)	0.0066 (3)	0.0006 (3)
C16	0.0139 (4)	0.0182 (4)	0.0158 (4)	0.0006 (3)	0.0068 (3)	0.0008 (3)
C17	0.0181 (4)	0.0178 (4)	0.0170 (4)	0.0014 (3)	0.0095 (3)	0.0009 (3)
C18	0.0177 (4)	0.0210 (4)	0.0232 (4)	0.0010 (3)	0.0120 (4)	0.0002 (3)
C19	0.0144 (4)	0.0220 (4)	0.0227 (4)	−0.0007 (3)	0.0091 (3)	−0.0004 (3)
C20	0.0147 (4)	0.0169 (4)	0.0173 (4)	0.0003 (3)	0.0063 (3)	−0.0004 (3)
C21	0.0220 (5)	0.0418 (7)	0.0282 (5)	0.0008 (5)	0.0092 (4)	0.0185 (5)
C22	0.0219 (5)	0.0267 (5)	0.0157 (4)	0.0015 (4)	0.0079 (3)	0.0021 (3)

Geometric parameters (Å, º)

O1—C1	1.3544 (11)	C9—C10	1.3858 (14)
O1—H1O1	0.8632	C9—H9A	0.9299
O2—C4	1.3729 (11)	C10—C11	1.3898 (14)
O2—C21	1.4253 (14)	C10—H10A	0.9300
O3—C20	1.3567 (12)	C11—C12	1.3893 (14)
O3—H1O3	0.8989	C11—H11A	0.9300
O4—C17	1.3702 (12)	C12—C13	1.4038 (13)
O4—C22	1.4247 (13)	C12—H12A	0.9299
N1—C7	1.2921 (12)	C14—C15	1.4511 (12)
N1—C8	1.4091 (12)	C14—H14A	0.9300
N2—C14	1.2877 (12)	C15—C16	1.4028 (13)
N2—C13	1.4133 (12)	C15—C20	1.4046 (13)
C1—C2	1.3939 (13)	C16—C17	1.3869 (12)
C1—C6	1.4080 (13)	C16—H16A	0.9299
C2—C3	1.3804 (13)	C17—C18	1.3972 (14)
C2—H2A	0.9301	C18—C19	1.3838 (14)
C3—C4	1.4040 (13)	C18—H18A	0.9301
C3—H3A	0.9300	C19—C20	1.4010 (13)
C4—C5	1.3819 (13)	C19—H19A	0.9300
C5—C6	1.4116 (13)	C21—H21A	0.9600
C5—H5A	0.9301	C21—H21B	0.9600
C6—C7	1.4487 (13)	C21—H21C	0.9600
C7—H7A	0.9300	C22—H22A	0.9600
C8—C9	1.4047 (13)	C22—H22B	0.9600
C8—C13	1.4067 (13)	C22—H22C	0.9600
C1—O1—H1O1	105.1	C11—C12—C13	120.69 (9)
C4—O2—C21	116.75 (8)	C11—C12—H12A	119.7
C20—O3—H1O3	107.5	C13—C12—H12A	119.7
C17—O4—C22	115.70 (7)	C12—C13—C8	119.18 (8)
C7—N1—C8	120.23 (8)	C12—C13—N2	123.15 (8)
C14—N2—C13	119.65 (8)	C8—C13—N2	117.66 (8)
O1—C1—C2	118.57 (8)	N2—C14—C15	122.02 (8)
O1—C1—C6	121.72 (8)	N2—C14—H14A	119.0
C2—C1—C6	119.70 (8)	C15—C14—H14A	119.0
C3—C2—C1	119.98 (8)	C16—C15—C20	119.82 (8)
C3—C2—H2A	120.0	C16—C15—C14	118.48 (8)
C1—C2—H2A	120.0	C20—C15—C14	121.69 (8)
C2—C3—C4	121.04 (9)	C17—C16—C15	120.62 (9)
C2—C3—H3A	119.5	C17—C16—H16A	119.7
C4—C3—H3A	119.5	C15—C16—H16A	119.7
O2—C4—C5	125.26 (9)	O4—C17—C16	123.95 (9)
O2—C4—C3	115.23 (8)	O4—C17—C18	116.73 (8)
C5—C4—C3	119.50 (8)	C16—C17—C18	119.31 (9)
C4—C5—C6	120.11 (8)	C19—C18—C17	120.66 (9)
C4—C5—H5A	119.9	C19—C18—H18A	119.7
C6—C5—H5A	119.9	C17—C18—H18A	119.7
C1—C6—C5	119.61 (8)	C18—C19—C20	120.52 (9)
C1—C6—C7	120.93 (8)	C18—C19—H19A	119.7
C5—C6—C7	119.35 (8)	C20—C19—H19A	119.7
N1—C7—C6	121.35 (8)	O3—C20—C19	119.07 (8)
N1—C7—H7A	119.3	O3—C20—C15	121.89 (8)
C6—C7—H7A	119.3	C19—C20—C15	119.03 (9)
C9—C8—C13	119.26 (8)	O2—C21—H21A	109.5
C9—C8—N1	121.69 (8)	O2—C21—H21B	109.5
C13—C8—N1	118.95 (8)	H21A—C21—H21B	109.5
C10—C9—C8	120.77 (9)	O2—C21—H21C	109.5
C10—C9—H9A	119.6	H21A—C21—H21C	109.5
C8—C9—H9A	119.6	H21B—C21—H21C	109.5
C9—C10—C11	119.99 (9)	O4—C22—H22A	109.5
C9—C10—H10A	120.0	O4—C22—H22B	109.5
C11—C10—H10A	120.0	H22A—C22—H22B	109.5
C12—C11—C10	120.03 (9)	O4—C22—H22C	109.5
C12—C11—H11A	120.0	H22A—C22—H22C	109.5
C10—C11—H11A	120.0	H22B—C22—H22C	109.5
O1—C1—C2—C3	179.42 (9)	C11—C12—C13—N2	176.98 (9)
C6—C1—C2—C3	0.79 (14)	C9—C8—C13—C12	1.49 (14)
C1—C2—C3—C4	1.13 (15)	N1—C8—C13—C12	−175.00 (9)
C21—O2—C4—C5	1.54 (16)	C9—C8—C13—N2	−178.22 (8)
C21—O2—C4—C3	−179.11 (10)	N1—C8—C13—N2	5.30 (13)
C2—C3—C4—O2	178.97 (9)	C14—N2—C13—C12	−22.97 (14)
C2—C3—C4—C5	−1.64 (15)	C14—N2—C13—C8	156.72 (9)
O2—C4—C5—C6	179.54 (9)	C13—N2—C14—C15	178.91 (8)
C3—C4—C5—C6	0.22 (15)	N2—C14—C15—C16	−174.80 (9)
O1—C1—C6—C5	179.24 (9)	N2—C14—C15—C20	5.98 (14)
C2—C1—C6—C5	−2.18 (14)	C20—C15—C16—C17	−0.26 (14)
O1—C1—C6—C7	−4.52 (14)	C14—C15—C16—C17	−179.49 (9)
C2—C1—C6—C7	174.06 (9)	C22—O4—C17—C16	6.82 (14)
C4—C5—C6—C1	1.67 (14)	C22—O4—C17—C18	−173.15 (9)
C4—C5—C6—C7	−174.63 (9)	C15—C16—C17—O4	−178.41 (9)
C8—N1—C7—C6	−171.09 (8)	C15—C16—C17—C18	1.56 (14)
C1—C6—C7—N1	1.04 (14)	O4—C17—C18—C19	178.40 (9)
C5—C6—C7—N1	177.29 (9)	C16—C17—C18—C19	−1.57 (15)
C7—N1—C8—C9	31.92 (13)	C17—C18—C19—C20	0.27 (15)
C7—N1—C8—C13	−151.68 (9)	C18—C19—C20—O3	179.90 (9)
C13—C8—C9—C10	1.17 (14)	C18—C19—C20—C15	1.03 (15)
N1—C8—C9—C10	177.55 (9)	C16—C15—C20—O3	−179.87 (9)
C8—C9—C10—C11	−2.66 (16)	C14—C15—C20—O3	−0.66 (14)
C9—C10—C11—C12	1.44 (16)	C16—C15—C20—C19	−1.03 (14)
C10—C11—C12—C13	1.25 (16)	C14—C15—C20—C19	178.18 (9)
C11—C12—C13—C8	−2.70 (15)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
O1—H1O1···N1	0.86	1.78	2.5811 (13)	153
O3—H1O3···N2	0.90	1.82	2.6285 (14)	148
C7—H7A···Cg2^i	0.93	2.82	3.2893 (11)	112
C22—H22C···Cg1^i	0.96	2.84	3.7312 (12)	155

Symmetry code: (i) x, −y−1/2, z−1/2.