Ethyl 2-[5-(4-fluoro-phen-yl)pyridin-3-yl]-1-[3-(2-oxopyrrolidin-1-yl)prop-yl]-1H-benzimidazole-5-carboxyl-ate.

In the title compound, C28H27FN4O3·H2O, the benzimidazole ring system is essentially planar with a maximum deviation of 0.028 (1) Å. It makes dihedral angles of 47.59 (5) and 60.31 (5)°, respectively, with the pyridine and benzene rings, which make a dihedral angle of 22.58 (6)° with each other. The pyrrolidine ring shows an envelope conformation with one of the methyl-ene C atoms as the flap. In the crystal, the components are connected into a tape along the b-axis direction through O-H⋯O and O-H⋯N hydrogen bonds and a π-π inter-action between the pyridine and benzene rings [centroid-centroid distance of 3.685 (8) Å]. The tapes are further linked into layers parallel to the ab plane by C-H⋯O and C-H⋯F inter-actions.

Related literature

For biological applications of benzimidazole derivatives, see: Tanious et al. (2004 ▶); Coburn et al. (1987 ▶); Rao et al. (2002 ▶). For a related structure, see: Yoon et al. (2012 ▶).

Experimental

Crystal data

C28H27FN4O3·H2O

M = 504.55

Monoclinic,

a = 16.0640 (15) Å

b = 7.6562 (7) Å

c = 20.1991 (19) Å

β = 98.163 (2)°

V = 2459.1 (4) Å3

Z = 4

Mo Kα radiation

μ = 0.10 mm−1

T = 100 K

0.35 × 0.33 × 0.21 mm

Data collection

Bruker APEX Duo CCD area-detector diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2009 ▶) T min = 0.967, T max = 0.980

24841 measured reflections

6502 independent reflections

5002 reflections with I > 2σ(I)

R int = 0.037

Refinement

R[F 2 > 2σ(F 2)] = 0.042

wR(F 2) = 0.113

S = 1.03

6502 reflections

343 parameters

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.31 e Å−3

Δρmin = −0.25 e Å−3

Data collection: APEX2 (Bruker, 2009 ▶); cell refinement: SAINT (Bruker, 2009 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXTL (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL and PLATON (Spek, 2009 ▶).

Crystal structure: contains datablock(s) I, New_Global_Publ_Block. DOI: 10.1107/S1600536813014177/is5275sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536813014177/is5275Isup2.hkl

Click here for additional data file.

Supplementary material file. DOI: 10.1107/S1600536813014177/is5275Isup3.cml

Additional supplementary materials: crystallographic information; 3D view; checkCIF report

C28H27FN4O3·H2O	F(000) = 1064
Mr = 504.55	Dx = 1.363 Mg m−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 7659 reflections
a = 16.0640 (15) Å	θ = 3.0–30.3°
b = 7.6562 (7) Å	µ = 0.10 mm−1
c = 20.1991 (19) Å	T = 100 K
β = 98.163 (2)°	Block, brown
V = 2459.1 (4) Å3	0.35 × 0.33 × 0.21 mm
Z = 4

Bruker APEX Duo CCD area-detector diffractometer	6502 independent reflections
Radiation source: fine-focus sealed tube	5002 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.037
φ and ω scans	θmax = 29.0°, θmin = 1.3°
Absorption correction: multi-scan (SADABS; Bruker, 2009)	h = −21→21
Tmin = 0.967, Tmax = 0.980	k = −8→10
24841 measured reflections	l = −25→27

Refinement on F2	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.042	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.113	H atoms treated by a mixture of independent and constrained refinement
S = 1.03	w = 1/[σ2(Fo2) + (0.0504P)2 + 0.8415P] where P = (Fo2 + 2Fc2)/3
6502 reflections	(Δ/σ)max < 0.001
343 parameters	Δρmax = 0.31 e Å−3
0 restraints	Δρmin = −0.25 e Å−3

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.

	x	y	z	Uiso*/Ueq
F1	0.00660 (5)	1.18506 (11)	0.02501 (4)	0.0277 (2)
O1	0.89089 (5)	0.94479 (13)	0.30464 (5)	0.0235 (2)
O2	0.92597 (6)	0.83605 (14)	0.20908 (5)	0.0283 (2)
O3	0.29289 (7)	0.45959 (15)	0.01770 (6)	0.0368 (3)
N1	0.52774 (6)	0.76622 (14)	0.16989 (5)	0.0155 (2)
N2	0.56706 (6)	0.87671 (14)	0.27305 (5)	0.0170 (2)
N3	0.31735 (7)	0.78858 (16)	0.31867 (6)	0.0205 (2)
N4	0.32987 (6)	0.73537 (15)	−0.01162 (5)	0.0182 (2)
C1	0.61471 (7)	0.77837 (16)	0.17809 (6)	0.0160 (2)
C2	0.67326 (8)	0.73151 (17)	0.13630 (7)	0.0184 (3)
H2A	0.6568	0.6795	0.0938	0.022*
C3	0.75670 (8)	0.76529 (17)	0.16049 (7)	0.0193 (3)
H3A	0.7987	0.7358	0.1337	0.023*
C4	0.78115 (7)	0.84195 (17)	0.22350 (7)	0.0178 (3)
C5	0.72238 (7)	0.88486 (17)	0.26539 (7)	0.0170 (2)
H5A	0.7390	0.9360	0.3081	0.020*
C6	0.63811 (7)	0.84952 (16)	0.24192 (6)	0.0159 (2)
C7	0.50329 (7)	0.82625 (16)	0.22826 (6)	0.0156 (2)
C8	0.41508 (7)	0.83587 (16)	0.24061 (6)	0.0158 (2)
C9	0.39447 (8)	0.77708 (17)	0.30149 (6)	0.0182 (3)
H9A	0.4376	0.7260	0.3325	0.022*
C10	0.25739 (8)	0.85882 (18)	0.27371 (7)	0.0191 (3)
H10A	0.2025	0.8688	0.2857	0.023*
C11	0.26951 (7)	0.91840 (16)	0.21053 (6)	0.0160 (2)
C12	0.35139 (7)	0.90683 (16)	0.19441 (6)	0.0163 (2)
H12A	0.3634	0.9471	0.1523	0.020*
C13	0.19944 (7)	0.99304 (16)	0.16271 (6)	0.0166 (2)
C14	0.21604 (8)	1.10604 (17)	0.11189 (7)	0.0187 (3)
H14A	0.2726	1.1379	0.1089	0.022*
C15	0.15166 (8)	1.17301 (18)	0.06552 (7)	0.0203 (3)
H15A	0.1634	1.2498	0.0311	0.024*
C16	0.07029 (8)	1.12430 (18)	0.07115 (7)	0.0206 (3)
C17	0.05031 (8)	1.01864 (18)	0.12132 (7)	0.0223 (3)
H17A	−0.0066	0.9914	0.1247	0.027*
C18	0.11554 (8)	0.95205 (18)	0.16728 (7)	0.0201 (3)
H18A	0.1029	0.8778	0.2022	0.024*
C19	0.47650 (7)	0.68575 (17)	0.11211 (6)	0.0162 (2)
H19A	0.4186	0.6689	0.1223	0.019*
H19B	0.4999	0.5693	0.1040	0.019*
C20	0.47344 (8)	0.79563 (18)	0.04903 (6)	0.0188 (3)
H20A	0.5313	0.8123	0.0385	0.023*
H20B	0.4500	0.9121	0.0569	0.023*
C21	0.41947 (7)	0.70879 (19)	−0.01050 (7)	0.0206 (3)
H21A	0.4361	0.7557	−0.0524	0.025*
H21B	0.4312	0.5818	−0.0093	0.025*
C22	0.29024 (8)	0.90041 (19)	−0.03556 (7)	0.0236 (3)
H22A	0.3130	0.9429	−0.0757	0.028*
H22B	0.2988	0.9913	−0.0004	0.028*
C23	0.19705 (9)	0.8521 (2)	−0.05240 (8)	0.0296 (3)
H23A	0.1606	0.9487	−0.0410	0.035*
H23B	0.1824	0.8238	−0.1005	0.035*
C24	0.18793 (9)	0.6929 (2)	−0.00927 (9)	0.0352 (4)
H24A	0.1457	0.6107	−0.0322	0.042*
H24B	0.1709	0.7270	0.0341	0.042*
C25	0.27508 (8)	0.6116 (2)	0.00055 (7)	0.0245 (3)
C26	0.87277 (8)	0.87268 (17)	0.24398 (7)	0.0204 (3)
C27	0.97999 (8)	0.9758 (2)	0.32679 (8)	0.0273 (3)
H27A	1.0033	1.0541	0.2950	0.033*
H27B	1.0113	0.8642	0.3291	0.033*
C28	0.98829 (9)	1.0583 (2)	0.39429 (8)	0.0316 (3)
H28A	1.0470	1.0917	0.4084	0.047*
H28B	0.9707	0.9750	0.4264	0.047*
H28C	0.9526	1.1625	0.3924	0.047*
O1W	0.41361 (6)	0.24454 (14)	0.08944 (6)	0.0233 (2)
H1W1	0.3772 (12)	0.315 (3)	0.0644 (10)	0.043 (5)*
H2W1	0.4181 (12)	0.291 (3)	0.1303 (12)	0.050 (6)*

	U11	U22	U33	U12	U13	U23
F1	0.0204 (4)	0.0310 (5)	0.0289 (5)	0.0040 (3)	−0.0065 (3)	0.0031 (4)
O1	0.0147 (4)	0.0285 (5)	0.0262 (5)	−0.0030 (4)	−0.0004 (4)	−0.0006 (4)
O2	0.0175 (4)	0.0359 (6)	0.0329 (6)	−0.0010 (4)	0.0080 (4)	−0.0008 (5)
O3	0.0320 (6)	0.0305 (6)	0.0450 (7)	−0.0029 (4)	−0.0040 (5)	0.0121 (5)
N1	0.0140 (5)	0.0197 (5)	0.0124 (5)	0.0003 (4)	0.0010 (4)	0.0001 (4)
N2	0.0157 (5)	0.0201 (5)	0.0153 (5)	0.0006 (4)	0.0021 (4)	0.0003 (4)
N3	0.0188 (5)	0.0269 (6)	0.0161 (6)	−0.0010 (4)	0.0030 (4)	0.0006 (5)
N4	0.0148 (5)	0.0238 (6)	0.0155 (5)	0.0014 (4)	0.0005 (4)	−0.0001 (4)
C1	0.0148 (5)	0.0173 (6)	0.0155 (6)	0.0005 (4)	0.0011 (4)	0.0031 (5)
C2	0.0191 (6)	0.0211 (6)	0.0151 (6)	0.0021 (5)	0.0027 (5)	0.0015 (5)
C3	0.0182 (6)	0.0211 (6)	0.0197 (7)	0.0028 (5)	0.0059 (5)	0.0043 (5)
C4	0.0154 (5)	0.0180 (6)	0.0196 (7)	0.0009 (4)	0.0012 (5)	0.0046 (5)
C5	0.0166 (6)	0.0177 (6)	0.0160 (6)	−0.0002 (4)	−0.0006 (4)	0.0016 (5)
C6	0.0161 (5)	0.0163 (6)	0.0153 (6)	0.0008 (4)	0.0020 (4)	0.0022 (5)
C7	0.0163 (5)	0.0168 (6)	0.0135 (6)	0.0011 (4)	0.0017 (4)	0.0022 (5)
C8	0.0150 (5)	0.0178 (6)	0.0147 (6)	−0.0013 (4)	0.0019 (4)	−0.0030 (5)
C9	0.0187 (6)	0.0224 (6)	0.0134 (6)	0.0000 (5)	0.0013 (4)	−0.0006 (5)
C10	0.0161 (6)	0.0238 (6)	0.0181 (6)	−0.0015 (5)	0.0043 (5)	−0.0014 (5)
C11	0.0150 (5)	0.0170 (6)	0.0158 (6)	−0.0014 (4)	0.0014 (4)	−0.0022 (5)
C12	0.0168 (5)	0.0184 (6)	0.0136 (6)	−0.0011 (4)	0.0021 (4)	−0.0008 (5)
C13	0.0151 (5)	0.0188 (6)	0.0157 (6)	−0.0004 (4)	0.0014 (4)	−0.0037 (5)
C14	0.0157 (5)	0.0211 (6)	0.0195 (7)	−0.0008 (4)	0.0030 (5)	−0.0020 (5)
C15	0.0211 (6)	0.0221 (6)	0.0178 (7)	0.0015 (5)	0.0028 (5)	0.0002 (5)
C16	0.0171 (6)	0.0226 (6)	0.0205 (7)	0.0042 (5)	−0.0031 (5)	−0.0027 (5)
C17	0.0146 (5)	0.0266 (7)	0.0253 (7)	−0.0002 (5)	0.0009 (5)	−0.0011 (6)
C18	0.0169 (6)	0.0236 (7)	0.0199 (7)	−0.0019 (5)	0.0026 (5)	0.0006 (5)
C19	0.0162 (5)	0.0188 (6)	0.0131 (6)	−0.0005 (4)	0.0007 (4)	−0.0013 (5)
C20	0.0162 (6)	0.0258 (7)	0.0141 (6)	−0.0028 (5)	0.0007 (4)	0.0010 (5)
C21	0.0143 (5)	0.0335 (7)	0.0140 (6)	0.0016 (5)	0.0020 (4)	−0.0020 (6)
C22	0.0247 (6)	0.0231 (7)	0.0225 (7)	0.0036 (5)	0.0009 (5)	0.0001 (6)
C23	0.0215 (6)	0.0345 (8)	0.0306 (8)	0.0084 (6)	−0.0038 (6)	−0.0057 (7)
C24	0.0166 (6)	0.0444 (9)	0.0438 (10)	−0.0016 (6)	0.0016 (6)	0.0020 (8)
C25	0.0200 (6)	0.0298 (7)	0.0224 (7)	−0.0022 (5)	−0.0016 (5)	0.0020 (6)
C26	0.0171 (6)	0.0187 (6)	0.0257 (7)	−0.0005 (5)	0.0034 (5)	0.0047 (5)
C27	0.0143 (6)	0.0300 (7)	0.0361 (9)	−0.0045 (5)	−0.0017 (5)	0.0020 (6)
C28	0.0267 (7)	0.0277 (8)	0.0370 (9)	−0.0032 (6)	−0.0068 (6)	0.0037 (7)
O1W	0.0215 (5)	0.0276 (5)	0.0209 (5)	−0.0001 (4)	0.0031 (4)	−0.0023 (4)

F1—C16	1.3642 (14)	C13—C18	1.3996 (17)
O1—C26	1.3378 (17)	C14—C15	1.3910 (18)
O1—C27	1.4571 (15)	C14—H14A	0.9500
O2—C26	1.2152 (16)	C15—C16	1.3793 (18)
O3—C25	1.2358 (18)	C15—H15A	0.9500
N1—C7	1.3737 (16)	C16—C17	1.370 (2)
N1—C1	1.3864 (15)	C17—C18	1.3939 (18)
N1—C19	1.4652 (15)	C17—H17A	0.9500
N2—C7	1.3244 (15)	C18—H18A	0.9500
N2—C6	1.3946 (16)	C19—C20	1.5216 (18)
N3—C9	1.3362 (16)	C19—H19A	0.9900
N3—C10	1.3391 (17)	C19—H19B	0.9900
N4—C25	1.3398 (18)	C20—C21	1.5309 (18)
N4—C21	1.4506 (15)	C20—H20A	0.9900
N4—C22	1.4658 (17)	C20—H20B	0.9900
C1—C2	1.3968 (18)	C21—H21A	0.9900
C1—C6	1.4010 (18)	C21—H21B	0.9900
C2—C3	1.3844 (17)	C22—C23	1.5327 (19)
C2—H2A	0.9500	C22—H22A	0.9900
C3—C4	1.4060 (19)	C22—H22B	0.9900
C3—H3A	0.9500	C23—C24	1.517 (2)
C4—C5	1.3934 (18)	C23—H23A	0.9900
C4—C26	1.4899 (17)	C23—H23B	0.9900
C5—C6	1.3959 (16)	C24—C25	1.519 (2)
C5—H5A	0.9500	C24—H24A	0.9900
C7—C8	1.4751 (16)	C24—H24B	0.9900
C8—C9	1.3928 (18)	C27—C28	1.491 (2)
C8—C12	1.3934 (17)	C27—H27A	0.9900
C9—H9A	0.9500	C27—H27B	0.9900
C10—C11	1.3947 (18)	C28—H28A	0.9800
C10—H10A	0.9500	C28—H28B	0.9800
C11—C12	1.4021 (17)	C28—H28C	0.9800
C11—C13	1.4891 (17)	O1W—H1W1	0.90 (2)
C12—H12A	0.9500	O1W—H2W1	0.89 (2)
C13—C14	1.3968 (19)
C26—O1—C27	115.15 (11)	C18—C17—H17A	120.8
C7—N1—C1	106.33 (10)	C17—C18—C13	120.93 (13)
C7—N1—C19	128.87 (10)	C17—C18—H18A	119.5
C1—N1—C19	124.47 (10)	C13—C18—H18A	119.5
C7—N2—C6	104.58 (10)	N1—C19—C20	112.47 (10)
C9—N3—C10	117.03 (12)	N1—C19—H19A	109.1
C25—N4—C21	125.03 (12)	C20—C19—H19A	109.1
C25—N4—C22	113.87 (11)	N1—C19—H19B	109.1
C21—N4—C22	120.64 (11)	C20—C19—H19B	109.1
N1—C1—C2	131.62 (12)	H19A—C19—H19B	107.8
N1—C1—C6	105.67 (11)	C19—C20—C21	111.41 (11)
C2—C1—C6	122.71 (11)	C19—C20—H20A	109.3
C3—C2—C1	116.11 (12)	C21—C20—H20A	109.3
C3—C2—H2A	121.9	C19—C20—H20B	109.3
C1—C2—H2A	121.9	C21—C20—H20B	109.3
C2—C3—C4	121.97 (12)	H20A—C20—H20B	108.0
C2—C3—H3A	119.0	N4—C21—C20	113.66 (11)
C4—C3—H3A	119.0	N4—C21—H21A	108.8
C5—C4—C3	121.45 (11)	C20—C21—H21A	108.8
C5—C4—C26	121.46 (12)	N4—C21—H21B	108.8
C3—C4—C26	117.08 (11)	C20—C21—H21B	108.8
C4—C5—C6	117.14 (12)	H21A—C21—H21B	107.7
C4—C5—H5A	121.4	N4—C22—C23	103.29 (11)
C6—C5—H5A	121.4	N4—C22—H22A	111.1
N2—C6—C5	129.37 (12)	C23—C22—H22A	111.1
N2—C6—C1	110.07 (10)	N4—C22—H22B	111.1
C5—C6—C1	120.55 (11)	C23—C22—H22B	111.1
N2—C7—N1	113.34 (10)	H22A—C22—H22B	109.1
N2—C7—C8	122.57 (11)	C24—C23—C22	103.74 (11)
N1—C7—C8	124.09 (11)	C24—C23—H23A	111.0
C9—C8—C12	118.26 (11)	C22—C23—H23A	111.0
C9—C8—C7	119.18 (11)	C24—C23—H23B	111.0
C12—C8—C7	122.53 (11)	C22—C23—H23B	111.0
N3—C9—C8	123.60 (12)	H23A—C23—H23B	109.0
N3—C9—H9A	118.2	C23—C24—C25	104.00 (12)
C8—C9—H9A	118.2	C23—C24—H24A	111.0
N3—C10—C11	124.86 (11)	C25—C24—H24A	111.0
N3—C10—H10A	117.6	C23—C24—H24B	111.0
C11—C10—H10A	117.6	C25—C24—H24B	111.0
C10—C11—C12	116.70 (11)	H24A—C24—H24B	109.0
C10—C11—C13	121.88 (11)	O3—C25—N4	125.84 (13)
C12—C11—C13	121.41 (11)	O3—C25—C24	126.49 (13)
C8—C12—C11	119.53 (12)	N4—C25—C24	107.66 (13)
C8—C12—H12A	120.2	O2—C26—O1	123.17 (12)
C11—C12—H12A	120.2	O2—C26—C4	123.42 (13)
C14—C13—C18	118.25 (11)	O1—C26—C4	113.41 (11)
C14—C13—C11	120.58 (11)	O1—C27—C28	107.83 (12)
C18—C13—C11	121.16 (12)	O1—C27—H27A	110.1
C15—C14—C13	121.46 (11)	C28—C27—H27A	110.1
C15—C14—H14A	119.3	O1—C27—H27B	110.1
C13—C14—H14A	119.3	C28—C27—H27B	110.1
C16—C15—C14	117.87 (13)	H27A—C27—H27B	108.5
C16—C15—H15A	121.1	C27—C28—H28A	109.5
C14—C15—H15A	121.1	C27—C28—H28B	109.5
F1—C16—C17	118.35 (11)	H28A—C28—H28B	109.5
F1—C16—C15	118.63 (12)	C27—C28—H28C	109.5
C17—C16—C15	123.02 (12)	H28A—C28—H28C	109.5
C16—C17—C18	118.40 (12)	H28B—C28—H28C	109.5
C16—C17—H17A	120.8	H1W1—O1W—H2W1	104.2 (18)
C7—N1—C1—C2	177.83 (13)	C13—C11—C12—C8	−179.92 (11)
C19—N1—C1—C2	3.9 (2)	C10—C11—C13—C14	156.88 (13)
C7—N1—C1—C6	−1.04 (13)	C12—C11—C13—C14	−22.24 (18)
C19—N1—C1—C6	−174.99 (11)	C10—C11—C13—C18	−23.22 (19)
N1—C1—C2—C3	178.99 (13)	C12—C11—C13—C18	157.65 (13)
C6—C1—C2—C3	−2.30 (19)	C18—C13—C14—C15	−1.8 (2)
C1—C2—C3—C4	0.13 (19)	C11—C13—C14—C15	178.05 (12)
C2—C3—C4—C5	1.2 (2)	C13—C14—C15—C16	0.0 (2)
C2—C3—C4—C26	−179.73 (12)	C14—C15—C16—F1	−178.27 (12)
C3—C4—C5—C6	−0.41 (19)	C14—C15—C16—C17	2.3 (2)
C26—C4—C5—C6	−179.42 (11)	F1—C16—C17—C18	178.03 (12)
C7—N2—C6—C5	177.95 (13)	C15—C16—C17—C18	−2.5 (2)
C7—N2—C6—C1	−1.19 (14)	C16—C17—C18—C13	0.5 (2)
C4—C5—C6—N2	179.24 (12)	C14—C13—C18—C17	1.6 (2)
C4—C5—C6—C1	−1.70 (18)	C11—C13—C18—C17	−178.31 (12)
N1—C1—C6—N2	1.40 (14)	C7—N1—C19—C20	115.93 (14)
C2—C1—C6—N2	−177.59 (12)	C1—N1—C19—C20	−71.54 (15)
N1—C1—C6—C5	−177.83 (11)	N1—C19—C20—C21	−179.93 (10)
C2—C1—C6—C5	3.18 (19)	C25—N4—C21—C20	−109.17 (15)
C6—N2—C7—N1	0.52 (14)	C22—N4—C21—C20	79.12 (15)
C6—N2—C7—C8	−179.04 (11)	C19—C20—C21—N4	80.43 (14)
C1—N1—C7—N2	0.34 (14)	C25—N4—C22—C23	−12.33 (16)
C19—N1—C7—N2	173.93 (12)	C21—N4—C22—C23	160.26 (12)
C1—N1—C7—C8	179.89 (11)	N4—C22—C23—C24	23.99 (15)
C19—N1—C7—C8	−6.5 (2)	C22—C23—C24—C25	−26.92 (16)
N2—C7—C8—C9	−45.73 (18)	C21—N4—C25—O3	3.8 (2)
N1—C7—C8—C9	134.76 (13)	C22—N4—C25—O3	176.05 (14)
N2—C7—C8—C12	132.21 (13)	C21—N4—C25—C24	−177.20 (12)
N1—C7—C8—C12	−47.30 (19)	C22—N4—C25—C24	−4.99 (17)
C10—N3—C9—C8	0.9 (2)	C23—C24—C25—O3	−160.64 (15)
C12—C8—C9—N3	−1.57 (19)	C23—C24—C25—N4	20.41 (17)
C7—C8—C9—N3	176.45 (12)	C27—O1—C26—O2	−0.48 (19)
C9—N3—C10—C11	0.8 (2)	C27—O1—C26—C4	179.56 (11)
N3—C10—C11—C12	−1.7 (2)	C5—C4—C26—O2	179.52 (13)
N3—C10—C11—C13	179.17 (12)	C3—C4—C26—O2	0.5 (2)
C9—C8—C12—C11	0.57 (18)	C5—C4—C26—O1	−0.52 (18)
C7—C8—C12—C11	−177.39 (11)	C3—C4—C26—O1	−179.57 (11)
C10—C11—C12—C8	0.91 (18)	C26—O1—C27—C28	179.18 (12)

D—H···A	D—H	H···A	D···A	D—H···A
O1W—H1W1···O3	0.90 (2)	1.89 (2)	2.7881 (16)	174.3 (19)
O1W—H2W1···N2i	0.89 (2)	2.04 (2)	2.9309 (16)	175 (2)
C14—H14A···O1Wii	0.95	2.49	3.4368 (17)	173
C17—H17A···O2iii	0.95	2.45	3.1768 (17)	133
C27—H27A···O2iv	0.99	2.45	3.2749 (18)	141
C28—H28B···F1i	0.98	2.43	3.2851 (18)	145

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O1W—H1W1⋯O3	0.90 (2)	1.89 (2)	2.7881 (16)	174.3 (19)
O1W—H2W1⋯N2i	0.89 (2)	2.04 (2)	2.9309 (16)	175 (2)
C14—H14A⋯O1W ii	0.95	2.49	3.4368 (17)	173
C17—H17A⋯O2iii	0.95	2.45	3.1768 (17)	133
C27—H27A⋯O2iv	0.99	2.45	3.2749 (18)	141
C28—H28B⋯F1i	0.98	2.43	3.2851 (18)	145

Symmetry codes: (i) ; (ii) ; (iii) ; (iv) .