Ethidium benzoate methanol monosolvate

In the title salt solvate (systematic name: 8-amino-5-ethyl-6-phenyl­phenanthridin-5-ium benzoate methanol monosolvate), C₂₁H₂₀N₃⁺·C₆H₅CO₂⁻·CH₃OH, two ethidium cations, C₂₁H₂₀N₃⁺, dimerize about a twofold axis through π–π inter­actions [inter-centroid separation = 3.6137 (4) Å]. The benzoate anions are connected through hydrogen bonding with the –NH₂ groups of the ethidium cations and the –OH group of the MeOH mol­ecule. The MeOH mol­ecule also accepts a hydrogen bond from the –NH₂ group of the ethidium cation. The result is a one-dimensional hydrogen-bonded chain along the b-axis direction.

Key indicators

Structure: I

• Single-crystal X-ray study
• T = 90 K
• Mean [sigma](C-C) = 0.002 Å
• R factor = 0.053
• wR factor = 0.150
• Data-to-parameter ratio = 19.1

checkCIF/PLATON results

No syntax errors found



Alert level C
PLAT410_ALERT_2_C Short Intra H...H Contact  H7       ..H14      .       1.92 Ang.
                                                      x,y,z  =      1_555 Check
PLAT906_ALERT_3_C Large K Value in the Analysis of Variance ......      2.719 Check
PLAT911_ALERT_3_C Missing FCF Refl Between Thmin & STh/L=    0.600          6 Report
              -24  0 10, -25  1 11, -25  1 12, -24  0 12, -24  0 14, -22  0 14,

Alert level G
PLAT007_ALERT_5_G Number of Unrefined Donor-H Atoms ..............          5 Report
              H2    H2A   H3A   H3B   H3
PLAT883_ALERT_1_G No Info/Value for _atom_sites_solution_primary .     Please Do !
PLAT899_ALERT_4_G SHELXL2018 is Deprecated and Succeeded by SHELXL     2019/3 Note
PLAT910_ALERT_3_G Missing # of FCF Reflection(s) Below Theta(Min).          1 Note
                1  1  0,
PLAT912_ALERT_4_G Missing # of FCF Reflections Above STh/L=  0.600        318 Note
PLAT941_ALERT_3_G Average HKL Measurement Multiplicity ...........        4.9 Low
PLAT969_ALERT_5_G The 'Henn et al.' R-Factor-gap value ...........       2.68 Note
              Predicted wR2: Based on SigI   2  5.61 or SHELX Weight 14.75       
PLAT978_ALERT_2_G Number C-C Bonds with Positive Residual Density.         16 Info

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

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

---

Computing details

8-Amino-5-ethyl-6-phenylphenanthridin-5-ium benzoate methanol monosolvate

Crystal data

C21H20N3^+·C7H5O2^−·CH4O	F(000) = 1984
Mr = 467.55	Dx = 1.312 Mg m^−3
Monoclinic, C2/c	Mo Kα radiation, λ = 0.71069 Å
a = 22.0407 (6) Å	Cell parameters from 6092 reflections
b = 12.4642 (3) Å	θ = 2.8–28.6°
c = 18.0706 (5) Å	µ = 0.09 mm^−1
β = 107.4952 (10)°	T = 90 K
V = 4734.7 (2) Å^3	Block, red
Z = 8	0.30 × 0.15 × 0.10 mm

Data collection

Bruker PHOTON II CPAD diffractometer	4736 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	Rint = 0.064
φ and ω scans	θmax = 29.2°, θmin = 1.9°
Absorption correction: multi-scan (SADABS; Krause et al., 2015)	h = −29→27
Tmin = 0.691, Tmax = 0.746	k = −16→15
29963 measured reflections	l = −24→24
6087 independent 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)] = 0.053	H-atom parameters constrained
wR(F^2) = 0.150	w = 1/[σ^2(Fo^2) + (0.0683P)^2 + 4.3384P] where P = (Fo^2 + 2Fc^2)/3
S = 1.05	(Δ/σ)max < 0.001
6087 reflections	Δρmax = 0.51 e Å^−3
319 parameters	Δρmin = −0.27 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.

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 > 2sigma(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.

All hydrogen atoms are geometrically fixed using a riding-model approximation with C—H = 0.95 (for phenyl), 0.98 (for methyl), 0.99 (for methylene), O—H = 0.84 and N—H = 0.88 Å.

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

	x	y	z	Uiso*/Ueq
N1	0.41329 (6)	0.45032 (9)	0.33925 (7)	0.0185 (3)
O1	0.69273 (5)	0.72829 (8)	0.31166 (7)	0.0271 (3)
C1	0.52679 (7)	0.33972 (11)	0.35270 (8)	0.0188 (3)
C2	0.52645 (7)	0.45352 (11)	0.35874 (8)	0.0187 (3)
C3	0.46802 (7)	0.28272 (11)	0.33491 (8)	0.0189 (3)
O2	0.69837 (6)	0.89712 (9)	0.27351 (7)	0.0308 (3)
C4	0.41035 (7)	0.33857 (11)	0.32620 (8)	0.0190 (3)
C5	0.58308 (7)	0.51335 (11)	0.36914 (8)	0.0203 (3)
H5	0.581926	0.589338	0.372557	0.024*
C6	0.46801 (7)	0.50549 (11)	0.35457 (8)	0.0184 (3)
O3	0.29255 (6)	0.86288 (10)	0.36827 (7)	0.0333 (3)
H3	0.297556	0.860786	0.324012	0.050*
N2	0.29253 (6)	0.12236 (10)	0.26776 (8)	0.0271 (3)
H2	0.256774	0.157719	0.261451	0.033*
H2A	0.291688	0.052819	0.259098	0.033*
C7	0.35174 (7)	0.28527 (12)	0.30498 (9)	0.0209 (3)
H7	0.313740	0.324333	0.300220	0.025*
C8	0.58634 (7)	0.28949 (12)	0.36280 (8)	0.0209 (3)
H8	0.588537	0.213396	0.361985	0.025*
C9	0.40670 (7)	0.11801 (12)	0.30101 (9)	0.0230 (3)
H9	0.405605	0.042653	0.292810	0.028*
C10	0.64007 (7)	0.46248 (12)	0.37438 (8)	0.0206 (3)
N3	0.69510 (7)	0.51611 (11)	0.38180 (9)	0.0291 (3)
H3A	0.695708	0.586676	0.383493	0.035*
H3B	0.730214	0.480361	0.384930	0.035*
C11	0.64045 (7)	0.34775 (12)	0.37364 (8)	0.0217 (3)
H11	0.679646	0.311216	0.380930	0.026*
C12	0.46366 (7)	0.17005 (12)	0.32241 (9)	0.0213 (3)
H12	0.501570	0.129871	0.329174	0.026*
C13	0.34882 (7)	0.17493 (12)	0.29078 (8)	0.0213 (3)
C14	0.35344 (7)	0.50599 (12)	0.33950 (9)	0.0218 (3)
H14	0.317546	0.478366	0.296421	0.026*
H14A	0.357563	0.583836	0.331271	0.026*
C15	0.46851 (7)	0.62318 (11)	0.36976 (8)	0.0195 (3)
C16	0.68832 (7)	0.82758 (12)	0.31927 (9)	0.0223 (3)
C17	0.67009 (7)	0.86787 (12)	0.38850 (9)	0.0236 (3)
C18	0.49149 (8)	0.66099 (13)	0.44535 (9)	0.0255 (3)
H18	0.503879	0.611805	0.487379	0.031*
C19	0.33973 (8)	0.48795 (14)	0.41613 (10)	0.0298 (4)
H19	0.340212	0.410852	0.426940	0.045*
H19A	0.297811	0.517464	0.412963	0.045*
H19B	0.372324	0.523897	0.457891	0.045*
C20	0.65307 (9)	0.97436 (14)	0.39351 (10)	0.0342 (4)
H20	0.652014	1.022597	0.352441	0.041*
C21	0.45042 (8)	0.69580 (12)	0.30839 (9)	0.0240 (3)
H21	0.434456	0.670472	0.256566	0.029*
C22	0.49639 (9)	0.77075 (13)	0.45959 (10)	0.0300 (4)
H22	0.511866	0.796341	0.511400	0.036*
C23	0.47885 (8)	0.84285 (13)	0.39869 (10)	0.0289 (4)
H23	0.482578	0.917811	0.408518	0.035*
C24	0.67216 (9)	0.79923 (14)	0.44987 (10)	0.0324 (4)
H24	0.683412	0.726078	0.447166	0.039*
C25	0.45578 (8)	0.80517 (13)	0.32318 (10)	0.0278 (3)
H25	0.443564	0.854601	0.281290	0.033*
C26	0.64006 (9)	0.94195 (15)	0.51899 (10)	0.0340 (4)
H26	0.629493	0.967049	0.563207	0.041*
C27	0.63763 (10)	1.01061 (15)	0.45818 (11)	0.0374 (4)
H27	0.625279	1.083222	0.460647	0.045*
C28	0.65795 (10)	0.83670 (15)	0.51494 (11)	0.0391 (4)
H28	0.660563	0.789493	0.557056	0.047*
C29	0.30916 (9)	0.76352 (14)	0.40501 (11)	0.0351 (4)
H29	0.354249	0.749124	0.412005	0.053*
H29A	0.283218	0.706941	0.372969	0.053*
H29B	0.301619	0.764985	0.455754	0.053*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
N1	0.0208 (6)	0.0152 (6)	0.0197 (6)	0.0019 (4)	0.0063 (5)	0.0003 (4)
O1	0.0308 (6)	0.0187 (5)	0.0341 (6)	0.0025 (4)	0.0133 (5)	0.0023 (4)
C1	0.0236 (7)	0.0166 (7)	0.0165 (6)	0.0012 (5)	0.0064 (5)	0.0007 (5)
C2	0.0223 (7)	0.0171 (7)	0.0160 (6)	0.0022 (5)	0.0048 (5)	0.0008 (5)
C3	0.0224 (7)	0.0166 (7)	0.0188 (7)	0.0010 (5)	0.0077 (6)	0.0001 (5)
O2	0.0429 (7)	0.0208 (6)	0.0331 (6)	−0.0014 (5)	0.0181 (5)	0.0030 (4)
C4	0.0244 (7)	0.0146 (7)	0.0179 (6)	0.0012 (5)	0.0064 (5)	−0.0007 (5)
C5	0.0243 (7)	0.0152 (7)	0.0212 (7)	0.0007 (5)	0.0065 (6)	0.0011 (5)
C6	0.0234 (7)	0.0155 (7)	0.0162 (6)	0.0011 (5)	0.0056 (5)	0.0010 (5)
O3	0.0448 (7)	0.0262 (6)	0.0324 (6)	0.0095 (5)	0.0169 (6)	0.0010 (5)
N2	0.0233 (7)	0.0180 (6)	0.0405 (8)	−0.0020 (5)	0.0102 (6)	−0.0053 (5)
C7	0.0209 (7)	0.0184 (7)	0.0247 (7)	0.0018 (5)	0.0085 (6)	0.0003 (5)
C8	0.0241 (7)	0.0159 (7)	0.0220 (7)	0.0031 (5)	0.0057 (6)	−0.0001 (5)
C9	0.0289 (8)	0.0157 (7)	0.0254 (7)	0.0003 (6)	0.0099 (6)	−0.0015 (5)
C10	0.0222 (7)	0.0201 (7)	0.0194 (7)	0.0001 (5)	0.0061 (6)	0.0016 (5)
N3	0.0231 (7)	0.0198 (6)	0.0457 (9)	0.0012 (5)	0.0122 (6)	0.0026 (6)
C11	0.0218 (7)	0.0209 (7)	0.0225 (7)	0.0039 (5)	0.0066 (6)	0.0013 (5)
C12	0.0236 (7)	0.0174 (7)	0.0232 (7)	0.0023 (5)	0.0077 (6)	−0.0002 (5)
C13	0.0248 (7)	0.0192 (7)	0.0209 (7)	−0.0012 (5)	0.0085 (6)	−0.0014 (5)
C14	0.0209 (7)	0.0158 (7)	0.0294 (8)	0.0030 (5)	0.0086 (6)	−0.0010 (5)
C15	0.0195 (7)	0.0157 (7)	0.0237 (7)	0.0012 (5)	0.0069 (6)	−0.0008 (5)
C16	0.0204 (7)	0.0200 (7)	0.0260 (7)	0.0001 (5)	0.0062 (6)	0.0009 (6)
C17	0.0238 (7)	0.0222 (7)	0.0239 (7)	−0.0019 (6)	0.0059 (6)	0.0005 (6)
C18	0.0320 (8)	0.0208 (7)	0.0221 (7)	0.0018 (6)	0.0059 (6)	0.0005 (6)
C19	0.0331 (9)	0.0253 (8)	0.0361 (9)	0.0038 (6)	0.0178 (7)	−0.0020 (6)
C20	0.0497 (11)	0.0247 (8)	0.0302 (9)	0.0074 (7)	0.0153 (8)	0.0053 (7)
C21	0.0282 (8)	0.0194 (7)	0.0225 (7)	0.0026 (6)	0.0048 (6)	0.0007 (5)
C22	0.0408 (10)	0.0232 (8)	0.0240 (8)	−0.0001 (7)	0.0068 (7)	−0.0048 (6)
C23	0.0345 (9)	0.0161 (7)	0.0347 (9)	0.0008 (6)	0.0082 (7)	−0.0033 (6)
C24	0.0453 (10)	0.0225 (8)	0.0312 (9)	0.0001 (7)	0.0140 (8)	0.0025 (6)
C25	0.0335 (9)	0.0185 (7)	0.0296 (8)	0.0043 (6)	0.0070 (7)	0.0036 (6)
C26	0.0395 (10)	0.0354 (9)	0.0285 (8)	−0.0029 (7)	0.0125 (7)	−0.0045 (7)
C27	0.0518 (12)	0.0271 (9)	0.0335 (9)	0.0075 (8)	0.0133 (8)	−0.0013 (7)
C28	0.0572 (12)	0.0304 (9)	0.0322 (9)	−0.0039 (8)	0.0174 (9)	0.0040 (7)
C29	0.0366 (10)	0.0297 (9)	0.0391 (10)	0.0067 (7)	0.0117 (8)	0.0031 (7)

Geometric parameters (Å, º)

N1—C6	1.3428 (19)	C12—H12	0.9500
N1—C4	1.4109 (18)	C14—C19	1.520 (2)
N1—C14	1.4917 (18)	C14—H14	0.9900
O1—C16	1.2523 (18)	C14—H14A	0.9900
C1—C8	1.416 (2)	C15—C18	1.389 (2)
C1—C2	1.423 (2)	C15—C21	1.394 (2)
C1—C3	1.427 (2)	C16—C17	1.510 (2)
C2—C5	1.417 (2)	C17—C20	1.390 (2)
C2—C6	1.423 (2)	C17—C24	1.390 (2)
C3—C4	1.416 (2)	C18—C22	1.390 (2)
C3—C12	1.421 (2)	C18—H18	0.9500
O2—C16	1.2626 (19)	C19—H19	0.9800
C4—C7	1.400 (2)	C19—H19A	0.9800
C5—C10	1.385 (2)	C19—H19B	0.9800
C5—H5	0.9500	C20—C27	1.387 (3)
C6—C15	1.4918 (19)	C20—H20	0.9500
O3—C29	1.401 (2)	C21—C25	1.387 (2)
O3—H3	0.8400	C21—H21	0.9500
N2—C13	1.353 (2)	C22—C23	1.383 (2)
N2—H2	0.8800	C22—H22	0.9500
N2—H2A	0.8800	C23—C25	1.387 (2)
C7—C13	1.397 (2)	C23—H23	0.9500
C7—H7	0.9500	C24—C28	1.386 (3)
C8—C11	1.359 (2)	C24—H24	0.9500
C8—H8	0.9500	C25—H25	0.9500
C9—C12	1.362 (2)	C26—C28	1.378 (3)
C9—C13	1.422 (2)	C26—C27	1.381 (3)
C9—H9	0.9500	C26—H26	0.9500
C10—N3	1.356 (2)	C27—H27	0.9500
C10—C11	1.430 (2)	C28—H28	0.9500
N3—H3A	0.8800	C29—H29	0.9800
N3—H3B	0.8800	C29—H29A	0.9800
C11—H11	0.9500	C29—H29B	0.9800
C6—N1—C4	122.23 (12)	C19—C14—H14A	109.5
C6—N1—C14	120.09 (12)	H14—C14—H14A	108.1
C4—N1—C14	117.61 (12)	C18—C15—C21	119.65 (14)
C8—C1—C2	117.20 (13)	C18—C15—C6	119.68 (13)
C8—C1—C3	123.55 (13)	C21—C15—C6	120.51 (13)
C2—C1—C3	119.23 (13)	O1—C16—O2	124.88 (15)
C5—C2—C1	120.66 (13)	O1—C16—C17	117.93 (13)
C5—C2—C6	120.96 (13)	O2—C16—C17	117.19 (13)
C1—C2—C6	118.38 (13)	C20—C17—C24	118.72 (15)
C4—C3—C12	116.91 (13)	C20—C17—C16	121.05 (14)
C4—C3—C1	120.27 (13)	C24—C17—C16	120.19 (14)
C12—C3—C1	122.78 (13)	C15—C18—C22	120.07 (14)
C7—C4—N1	120.44 (13)	C15—C18—H18	120.0
C7—C4—C3	121.39 (13)	C22—C18—H18	120.0
N1—C4—C3	118.17 (13)	C14—C19—H19	109.5
C10—C5—C2	120.85 (13)	C14—C19—H19A	109.5
C10—C5—H5	119.6	H19—C19—H19A	109.5
C2—C5—H5	119.6	C14—C19—H19B	109.5
N1—C6—C2	121.34 (13)	H19—C19—H19B	109.5
N1—C6—C15	119.87 (13)	H19A—C19—H19B	109.5
C2—C6—C15	118.77 (13)	C27—C20—C17	120.36 (16)
C29—O3—H3	109.5	C27—C20—H20	119.8
C13—N2—H2	120.0	C17—C20—H20	119.8
C13—N2—H2A	120.0	C25—C21—C15	119.84 (14)
H2—N2—H2A	120.0	C25—C21—H21	120.1
C13—C7—C4	120.35 (13)	C15—C21—H21	120.1
C13—C7—H7	119.8	C23—C22—C18	120.30 (15)
C4—C7—H7	119.8	C23—C22—H22	119.8
C11—C8—C1	121.44 (14)	C18—C22—H22	119.8
C11—C8—H8	119.3	C22—C23—C25	119.67 (15)
C1—C8—H8	119.3	C22—C23—H23	120.2
C12—C9—C13	120.90 (14)	C25—C23—H23	120.2
C12—C9—H9	119.5	C28—C24—C17	120.51 (16)
C13—C9—H9	119.5	C28—C24—H24	119.7
N3—C10—C5	123.17 (14)	C17—C24—H24	119.7
N3—C10—C11	119.10 (14)	C23—C25—C21	120.46 (15)
C5—C10—C11	117.71 (13)	C23—C25—H25	119.8
C10—N3—H3A	120.0	C21—C25—H25	119.8
C10—N3—H3B	120.0	C28—C26—C27	119.40 (17)
H3A—N3—H3B	120.0	C28—C26—H26	120.3
C8—C11—C10	121.88 (14)	C27—C26—H26	120.3
C8—C11—H11	119.1	C26—C27—C20	120.51 (17)
C10—C11—H11	119.1	C26—C27—H27	119.7
C9—C12—C3	121.90 (14)	C20—C27—H27	119.7
C9—C12—H12	119.1	C26—C28—C24	120.48 (17)
C3—C12—H12	119.1	C26—C28—H28	119.8
N2—C13—C7	121.36 (14)	C24—C28—H28	119.8
N2—C13—C9	120.13 (13)	O3—C29—H29	109.5
C7—C13—C9	118.51 (13)	O3—C29—H29A	109.5
N1—C14—C19	110.62 (12)	H29—C29—H29A	109.5
N1—C14—H14	109.5	O3—C29—H29B	109.5
C19—C14—H14	109.5	H29—C29—H29B	109.5
N1—C14—H14A	109.5	H29A—C29—H29B	109.5
C8—C1—C2—C5	4.2 (2)	C5—C10—C11—C8	4.5 (2)
C3—C1—C2—C5	−174.09 (13)	C13—C9—C12—C3	−0.4 (2)
C8—C1—C2—C6	−175.42 (12)	C4—C3—C12—C9	1.7 (2)
C3—C1—C2—C6	6.3 (2)	C1—C3—C12—C9	−176.06 (14)
C8—C1—C3—C4	179.54 (13)	C4—C7—C13—N2	−177.83 (14)
C2—C1—C3—C4	−2.3 (2)	C4—C7—C13—C9	2.2 (2)
C8—C1—C3—C12	−2.8 (2)	C12—C9—C13—N2	178.47 (14)
C2—C1—C3—C12	175.40 (13)	C12—C9—C13—C7	−1.5 (2)
C6—N1—C4—C7	−175.44 (13)	C6—N1—C14—C19	−98.78 (15)
C14—N1—C4—C7	7.59 (19)	C4—N1—C14—C19	78.27 (16)
C6—N1—C4—C3	4.3 (2)	N1—C6—C15—C18	103.00 (17)
C14—N1—C4—C3	−172.63 (12)	C2—C6—C15—C18	−75.35 (19)
C12—C3—C4—C7	−1.0 (2)	N1—C6—C15—C21	−81.64 (18)
C1—C3—C4—C7	176.79 (13)	C2—C6—C15—C21	100.00 (17)
C12—C3—C4—N1	179.18 (12)	O1—C16—C17—C20	−168.22 (16)
C1—C3—C4—N1	−3.0 (2)	O2—C16—C17—C20	12.2 (2)
C1—C2—C5—C10	−0.6 (2)	O1—C16—C17—C24	14.0 (2)
C6—C2—C5—C10	178.99 (13)	O2—C16—C17—C24	−165.61 (16)
C4—N1—C6—C2	−0.2 (2)	C21—C15—C18—C22	0.0 (2)
C14—N1—C6—C2	176.68 (12)	C6—C15—C18—C22	175.40 (15)
C4—N1—C6—C15	−178.53 (12)	C24—C17—C20—C27	−0.9 (3)
C14—N1—C6—C15	−1.6 (2)	C16—C17—C20—C27	−178.76 (17)
C5—C2—C6—N1	175.22 (13)	C18—C15—C21—C25	0.3 (2)
C1—C2—C6—N1	−5.2 (2)	C6—C15—C21—C25	−175.05 (14)
C5—C2—C6—C15	−6.5 (2)	C15—C18—C22—C23	−0.4 (3)
C1—C2—C6—C15	173.15 (12)	C18—C22—C23—C25	0.5 (3)
N1—C4—C7—C13	178.89 (13)	C20—C17—C24—C28	−0.5 (3)
C3—C4—C7—C13	−0.9 (2)	C16—C17—C24—C28	177.42 (16)
C2—C1—C8—C11	−3.5 (2)	C22—C23—C25—C21	−0.2 (3)
C3—C1—C8—C11	174.73 (14)	C15—C21—C25—C23	−0.2 (3)
C2—C5—C10—N3	177.79 (14)	C28—C26—C27—C20	−0.1 (3)
C2—C5—C10—C11	−3.7 (2)	C17—C20—C27—C26	1.2 (3)
C1—C8—C11—C10	−0.9 (2)	C27—C26—C28—C24	−1.3 (3)
N3—C10—C11—C8	−176.92 (14)	C17—C24—C28—C26	1.6 (3)

Hydrogen-bond geometry (Å, º)

Hydrogen-bond geometry (Å, °).

D—H···A	D—H	H···A	D···A	D—H···A
O3—H3···O2^i	0.84	1.85	2.6636 (17)	163
N2—H2···O1^ii	0.88	2.09	2.8741 (18)	148
N2—H2A···O2^iii	0.88	2.06	2.9271 (17)	169
N3—H3A···O1	0.88	2.18	2.9264 (18)	142
N3—H3B···O3^iv	0.88	2.09	2.939 (2)	162

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