2-Bromo-N′-[(E)-(4-fluoro­phen­yl)methyl­ene]-5-methoxy­benzohydrazide monohydrate

The crystal packing of the title compound, C₁₅H₁₂BrFN₂O₂·H₂O, is stabilized by N—H...O and O—H...O hydrogen bonds. There are two mol­ecules in the asymmetric unit, differing in the dihedral angle between the two aromatic rings, which are 62.3 (2) and 49.9 (2)°.

Key indicators

• Single-crystal X-ray study
• T = 173 K
• Mean [sigma](C-C) = 0.013 Å
• R factor = 0.080
• wR factor = 0.202
• Data-to-parameter ratio = 13.7

checkCIF/PLATON results

No syntax errors found



Alert level C
PLAT341_ALERT_3_C Low Bond Precision on C-C Bonds (x 1000) Ang ...         13
PLAT431_ALERT_2_C Short Inter HL..A Contact  Br1    ..  N2A     ..       3.39 Ang.
PLAT720_ALERT_4_C Number of Unusual/Non-Standard Label(s) ........          5

Alert level G
REFLT03_ALERT_4_G Please check that the estimate of the number of Friedel pairs is
            correct. If it is not, please give the correct count in the
            _publ_section_exptl_refinement section of the submitted CIF.
           From the CIF: _diffrn_reflns_theta_max           25.64
           From the CIF: _reflns_number_total               5477
           Count of symmetry unique reflns         2862
           Completeness (_total/calc)            191.37%
           TEST3: Check Friedels for noncentro structure
           Estimate of Friedel pairs measured      2615
           Fraction of Friedel pairs measured     0.914
           Are heavy atom types Z>Si present        yes
PLAT860_ALERT_3_G Note: Number of Least-Squares Restraints .......          2

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

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

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S1. Comment

Schiff bases are used as substrates in the preparation of number of industrial and biologically active compounds via ring closure, cycloaddition and replacement reactions. Some Schiff base derivatives were reported to possess antimicrobial, anti-inflammatory and central nervous system activities. Moreover, Schiff bases are also known to have biological activities such as antimicrobial, antifungal, antitumor, and as herbicides. A new Schiff base, (I), C₁₅H₁₂BrFN₂O₂.H₂O is synthesized and its crystal structure is reported.

The two molecules in the asymmetric unit differ in the dihedral angle between the two aromatic rings, which are 62.3 (2)° and 49.9 (2)°. The crystal packing is stabilized by N—H···O and O—H···O hydrogen bonds.

Related literature

For related structures, see: 2'-[1-(4-fluorophenyl)ethyl]isonicotino-_KN-hydrazide-cyanoborane (Bruno et al., 1998); 1-(2-bromo-5-methoxyphenyl)-8-chloro-6-(2-fluorophenyl)-4H-1,2,4-triazolo[4,3-a] [1,4]benzodiazepine (Harrison et al., 2005); 2-bromo-5-methoxy-N'-[(E)-(2-nitrophenyl)methylene]benzohydrazide (Yathirajan, Sarojini et al., 2007); N'-[(1E)-(4-fluorophenyl)methylene]-6-methoxy-2-naphthohydrazide (Yathirajan, Narayana, et al., 2007). For related literature, see: Varma et al. (1986); Misra et al. (1981); Agarwal et al. (1983); Singh et al. (1988); Hodnett et al. (1970).

S2. Experimental

A mixture of 2-bromo-5-methoxybenzohydrazide (0.735 g, 0.003 mol) and 4-fluorobenzaldehyde (0.372 g, 0.003 mol) in 15 ml of absolute alcohol containing 2 drops of 4 M sulfuric acid was refluxed for about 3 h (see scheme). On cooling, the solid separated was filtered off and recrystallized from ethyl acetate (m.p.: 440–442 K). Analysis for C₁₅H₁₂BrFN₂O₂.H₂O: Found (calculated): C 48.71 (48.80), H 3.76 (3.82), N 7.51 (7.59) %.

S3. Refinement

H atoms were found in a difference map, but they were refined using a riding model with C—H = 0.95 Å, N—H = 0.88 Å, O—H = 0.84Å and U_iso(H) = 1.2U_eq(C,N,O) or C—H = 0.98Å and U_iso(H) = 1.5U_eq(C_methyl).

Computing details

Data collection: X-AREA (Stoe & Cie, 2001); cell refinement: X-AREA; data reduction: X-AREA; program(s) used to solve structure: SHELXS97 (Sheldrick, 1990); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: PLATON (Spek, 2003); software used to prepare material for publication: SHELXL97.

Figures

Fig. 1. The structure of the two independent molecules in the asymmetric unit of the title compound, with the atom numbering. Displacement ellipsoids are at the 50% probability level.

2-Bromo-N'-[(1E)-(4-fluorophenyl)methylene]-5-methoxybenzohydrazide monohydrate

Crystal data

C15H12BrFN2O2.H2O	F(000) = 1488
Mr = 369.19	Dx = 1.625 Mg m^−3
Monoclinic, Cc	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: C -2yc	Cell parameters from 11319 reflections
a = 30.1171 (18) Å	θ = 3.6–25.1°
b = 8.0187 (7) Å	µ = 2.75 mm^−1
c = 13.4661 (8) Å	T = 173 K
β = 111.902 (4)°	Block, colourless
V = 3017.3 (4) Å^3	0.37 × 0.35 × 0.33 mm
Z = 8

Data collection

STOE IPDS II two-circle- diffractometer	5477 independent reflections
Radiation source: fine-focus sealed tube	4843 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.059
ω scans	θmax = 25.6°, θmin = 3.5°
Absorption correction: multi-scan (MULABS; Spek, 2003; Blessing, 1995)	h = −36→35
Tmin = 0.379, Tmax = 0.394	k = −9→9
16531 measured reflections	l = −16→16

Refinement

Refinement on F^2	Hydrogen site location: inferred from neighbouring sites
Least-squares matrix: full	H-atom parameters constrained
R[F^2 > 2σ(F^2)] = 0.080	w = 1/[σ^2(Fo^2) + (0.163P)^2] where P = (Fo^2 + 2Fc^2)/3
wR(F^2) = 0.202	(Δ/σ)max < 0.001
S = 1.02	Δρmax = 0.56 e Å^−3
5477 reflections	Δρmin = −0.76 e Å^−3
400 parameters	Extinction correction: SHELXL, Fc^*=kFc[1+0.001xFc^2λ^3/sin(2θ)]^-1/4
2 restraints	Extinction coefficient: 0.0062 (8)
Primary atom site location: structure-invariant direct methods	Absolute structure: Flack (1983), 2642 Friedel pairs
Secondary atom site location: difference Fourier map	Absolute structure parameter: 0.018 (17)

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
Br1	0.52393 (3)	0.24296 (11)	0.77882 (6)	0.0677 (3)
F1	0.82483 (19)	0.6614 (8)	0.6074 (5)	0.0838 (15)
O1	0.5622 (2)	0.5636 (7)	0.6968 (4)	0.0603 (12)
O2	0.3807 (2)	0.4246 (8)	0.3428 (5)	0.0697 (14)
N1	0.5647 (3)	0.4797 (9)	0.5375 (5)	0.0578 (14)
H1	0.5499	0.4312	0.4752	0.069*
N2	0.6106 (2)	0.5460 (8)	0.5654 (5)	0.0548 (13)
C1	0.5439 (3)	0.4937 (9)	0.6110 (6)	0.0557 (15)
C2	0.6317 (3)	0.5090 (10)	0.5039 (7)	0.0594 (17)
H2	0.6153	0.4475	0.4404	0.071*
C11	0.4947 (3)	0.4167 (8)	0.5755 (6)	0.0540 (15)
C12	0.4806 (3)	0.3189 (9)	0.6429 (5)	0.0555 (15)
C13	0.4333 (3)	0.2595 (9)	0.6109 (7)	0.0584 (17)
H13	0.4237	0.1914	0.6571	0.070*
C14	0.4013 (3)	0.3030 (12)	0.5107 (7)	0.0623 (19)
H14	0.3689	0.2680	0.4893	0.075*
C15	0.4150 (3)	0.3964 (10)	0.4402 (7)	0.0605 (17)
C16	0.4613 (3)	0.4553 (9)	0.4731 (6)	0.0568 (16)
H16	0.4707	0.5222	0.4261	0.068*
C17	0.3953 (3)	0.5087 (12)	0.2651 (7)	0.070 (2)
H17A	0.4090	0.6176	0.2933	0.105*
H17B	0.3674	0.5243	0.1986	0.105*
H17C	0.4193	0.4412	0.2506	0.105*
C21	0.6819 (3)	0.5605 (10)	0.5292 (6)	0.0554 (15)
C22	0.7068 (3)	0.4959 (10)	0.4660 (7)	0.0625 (17)
H22	0.6901	0.4297	0.4049	0.075*
C23	0.7554 (3)	0.5292 (11)	0.4933 (7)	0.0629 (18)
H23	0.7725	0.4847	0.4528	0.076*
C24	0.7774 (3)	0.6282 (11)	0.5806 (7)	0.0648 (19)
C25	0.7545 (3)	0.6977 (11)	0.6432 (7)	0.0661 (18)
H25	0.7712	0.7684	0.7019	0.079*
C26	0.7071 (3)	0.6607 (9)	0.6175 (6)	0.0583 (16)
H26	0.6910	0.7039	0.6605	0.070*
Br1A	0.15181 (3)	0.26881 (10)	0.25235 (4)	0.0646 (3)
C1A	0.1256 (3)	0.4374 (10)	0.0114 (6)	0.0569 (16)
F1A	−0.1718 (2)	0.6188 (9)	−0.1250 (5)	0.0903 (17)
O1A	0.1093 (2)	0.3990 (7)	−0.0840 (4)	0.0620 (12)
O2A	0.2918 (2)	0.3916 (8)	0.0344 (5)	0.0682 (14)
N1A	0.0998 (2)	0.5084 (9)	0.0612 (5)	0.0583 (14)
H1A	0.1135	0.5470	0.1268	0.070*
N2A	0.0509 (3)	0.5199 (8)	0.0075 (5)	0.0576 (15)
C2A	0.0269 (3)	0.5737 (10)	0.0615 (6)	0.0597 (16)
H2A	0.0430	0.6068	0.1339	0.072*
C11A	0.1769 (3)	0.3985 (8)	0.0781 (6)	0.0543 (15)
C12A	0.1936 (3)	0.3191 (9)	0.1777 (6)	0.0551 (15)
C13A	0.2403 (3)	0.2667 (10)	0.2268 (7)	0.0604 (17)
H13A	0.2504	0.2118	0.2941	0.072*
C14A	0.2724 (3)	0.2947 (10)	0.1770 (8)	0.0645 (18)
H14A	0.3048	0.2601	0.2108	0.077*
C15A	0.2577 (3)	0.3727 (10)	0.0784 (6)	0.0606 (16)
C16A	0.2104 (3)	0.4230 (10)	0.0277 (6)	0.0565 (16)
H16A	0.2004	0.4739	−0.0409	0.068*
C17A	0.2772 (3)	0.4652 (12)	−0.0697 (7)	0.071 (2)
H17D	0.2507	0.4004	−0.1200	0.107*
H17E	0.3042	0.4654	−0.0936	0.107*
H17F	0.2666	0.5800	−0.0667	0.107*
C21A	−0.0256 (3)	0.5847 (10)	0.0117 (7)	0.0625 (18)
C22A	−0.0509 (3)	0.6564 (10)	0.0689 (8)	0.0665 (18)
H22A	−0.0343	0.6958	0.1397	0.080*
C23A	−0.1008 (3)	0.6706 (12)	0.0220 (9)	0.073 (2)
H23A	−0.1185	0.7223	0.0590	0.088*
C24A	−0.1232 (3)	0.6070 (13)	−0.0792 (8)	0.077 (2)
C25A	−0.0994 (3)	0.5372 (13)	−0.1390 (8)	0.073 (2)
H25A	−0.1163	0.5000	−0.2101	0.088*
C26A	−0.0501 (3)	0.5231 (9)	−0.0922 (7)	0.0611 (17)
H26A	−0.0328	0.4717	−0.1302	0.073*
O1W	0.5235 (2)	0.2938 (8)	0.3394 (5)	0.0634 (12)
H1W1	0.5349	0.3360	0.2969	0.076*
H1W2	0.5488	0.2372	0.3619	0.076*
O1WA	0.1404 (2)	0.7000 (7)	0.2531 (4)	0.0585 (12)
H1W3	0.1178	0.7686	0.2367	0.070*
H1W4	0.1311	0.6703	0.3020	0.070*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
Br1	0.0677 (5)	0.0716 (5)	0.0613 (5)	−0.0041 (4)	0.0213 (4)	0.0093 (3)
F1	0.055 (3)	0.098 (4)	0.102 (4)	−0.007 (2)	0.033 (3)	0.007 (3)
O1	0.059 (3)	0.067 (3)	0.060 (3)	−0.003 (2)	0.027 (2)	−0.004 (2)
O2	0.056 (3)	0.081 (4)	0.068 (3)	−0.003 (3)	0.019 (3)	0.005 (3)
N1	0.057 (4)	0.059 (3)	0.055 (3)	−0.004 (3)	0.018 (3)	−0.004 (3)
N2	0.051 (3)	0.057 (3)	0.055 (3)	0.001 (2)	0.019 (3)	0.001 (2)
C1	0.057 (4)	0.053 (3)	0.057 (4)	0.000 (3)	0.020 (3)	−0.003 (3)
C2	0.058 (4)	0.055 (4)	0.060 (4)	0.001 (3)	0.017 (3)	0.001 (3)
C11	0.049 (4)	0.048 (3)	0.068 (4)	0.002 (3)	0.025 (3)	−0.003 (3)
C12	0.056 (4)	0.060 (4)	0.045 (3)	0.007 (3)	0.013 (3)	0.002 (3)
C13	0.063 (4)	0.055 (4)	0.065 (4)	−0.003 (3)	0.032 (4)	−0.003 (3)
C14	0.050 (4)	0.066 (5)	0.076 (5)	−0.002 (3)	0.029 (4)	−0.006 (3)
C15	0.062 (4)	0.054 (4)	0.066 (4)	0.000 (3)	0.025 (4)	−0.004 (3)
C16	0.065 (4)	0.051 (3)	0.061 (4)	−0.004 (3)	0.032 (3)	0.001 (3)
C17	0.062 (5)	0.079 (5)	0.061 (4)	−0.004 (4)	0.015 (4)	0.003 (4)
C21	0.054 (4)	0.057 (4)	0.058 (4)	0.003 (3)	0.024 (3)	0.010 (3)
C22	0.071 (5)	0.055 (4)	0.062 (4)	−0.002 (3)	0.025 (4)	0.004 (3)
C23	0.062 (4)	0.067 (4)	0.071 (4)	0.007 (3)	0.038 (4)	0.007 (3)
C24	0.058 (4)	0.070 (5)	0.070 (4)	0.003 (3)	0.029 (4)	0.017 (4)
C25	0.066 (5)	0.064 (4)	0.063 (4)	−0.006 (4)	0.018 (4)	0.006 (3)
C26	0.058 (4)	0.056 (4)	0.067 (4)	0.005 (3)	0.030 (3)	0.007 (3)
Br1A	0.0716 (5)	0.0638 (4)	0.0619 (5)	0.0006 (4)	0.0291 (4)	0.0058 (4)
C1A	0.058 (4)	0.052 (4)	0.060 (4)	−0.001 (3)	0.021 (3)	0.001 (3)
F1A	0.059 (3)	0.117 (5)	0.097 (4)	0.014 (3)	0.031 (3)	0.027 (3)
O1A	0.055 (3)	0.076 (3)	0.053 (2)	0.003 (2)	0.019 (2)	−0.004 (2)
O2A	0.055 (3)	0.073 (3)	0.077 (4)	0.001 (3)	0.026 (3)	−0.001 (3)
N1A	0.055 (3)	0.061 (3)	0.056 (3)	0.001 (3)	0.018 (3)	−0.005 (2)
N2A	0.056 (4)	0.057 (3)	0.058 (3)	0.000 (3)	0.018 (3)	−0.001 (3)
C2A	0.059 (4)	0.053 (4)	0.063 (4)	0.003 (3)	0.018 (3)	0.002 (3)
C11A	0.054 (4)	0.048 (3)	0.061 (4)	−0.001 (3)	0.022 (3)	−0.002 (3)
C12A	0.058 (4)	0.056 (3)	0.058 (4)	−0.004 (3)	0.029 (3)	0.000 (3)
C13A	0.062 (5)	0.060 (4)	0.054 (4)	0.007 (3)	0.017 (3)	0.000 (3)
C14A	0.059 (4)	0.056 (4)	0.074 (5)	0.004 (3)	0.019 (4)	−0.006 (3)
C15A	0.057 (4)	0.058 (4)	0.068 (4)	−0.002 (3)	0.025 (3)	−0.010 (3)
C16A	0.058 (4)	0.054 (4)	0.054 (3)	−0.001 (3)	0.017 (3)	−0.004 (3)
C17A	0.069 (5)	0.075 (5)	0.074 (5)	0.000 (4)	0.031 (4)	0.000 (4)
C21A	0.059 (4)	0.055 (4)	0.074 (5)	0.002 (3)	0.026 (4)	0.003 (3)
C22A	0.065 (5)	0.061 (4)	0.079 (5)	−0.001 (3)	0.033 (4)	−0.001 (3)
C23A	0.071 (5)	0.055 (4)	0.106 (7)	0.007 (3)	0.046 (5)	0.009 (4)
C24A	0.059 (5)	0.087 (6)	0.085 (6)	0.003 (4)	0.026 (4)	0.021 (5)
C25A	0.062 (5)	0.087 (6)	0.072 (5)	−0.009 (4)	0.027 (4)	0.004 (4)
C26A	0.061 (4)	0.057 (4)	0.069 (4)	0.005 (3)	0.029 (4)	0.012 (3)
O1W	0.062 (3)	0.067 (3)	0.062 (3)	0.002 (2)	0.023 (3)	−0.003 (2)
O1WA	0.060 (3)	0.060 (3)	0.057 (3)	0.006 (2)	0.023 (2)	0.004 (2)

Geometric parameters (Å, º)

Br1—C12	1.908 (7)	C1A—N1A	1.331 (11)
F1—C24	1.363 (10)	C1A—C11A	1.501 (11)
O1—C1	1.216 (9)	F1A—C24A	1.363 (11)
O2—C15	1.352 (11)	O2A—C15A	1.371 (10)
O2—C17	1.444 (11)	O2A—C17A	1.431 (11)
N1—C1	1.358 (10)	N1A—N2A	1.378 (10)
N1—N2	1.396 (10)	N1A—H1A	0.8800
N1—H1	0.8800	N2A—C2A	1.276 (11)
N2—C2	1.254 (11)	C2A—C21A	1.474 (12)
C1—C11	1.510 (10)	C2A—H2A	0.9500
C2—C21	1.480 (12)	C11A—C12A	1.398 (10)
C2—H2	0.9500	C11A—C16A	1.425 (11)
C11—C12	1.381 (11)	C12A—C13A	1.380 (12)
C11—C16	1.405 (11)	C13A—C14A	1.385 (14)
C12—C13	1.408 (12)	C13A—H13A	0.9500
C13—C14	1.379 (13)	C14A—C15A	1.382 (13)
C13—H13	0.9500	C14A—H14A	0.9500
C14—C15	1.386 (12)	C15A—C16A	1.390 (12)
C14—H14	0.9500	C16A—H16A	0.9500
C15—C16	1.380 (11)	C17A—H17D	0.9800
C16—H16	0.9500	C17A—H17E	0.9800
C17—H17A	0.9800	C17A—H17F	0.9800
C17—H17B	0.9800	C21A—C22A	1.393 (12)
C17—H17C	0.9800	C21A—C26A	1.405 (12)
C21—C26	1.401 (12)	C22A—C23A	1.400 (13)
C21—C22	1.423 (12)	C22A—H22A	0.9500
C22—C23	1.396 (13)	C23A—C24A	1.373 (16)
C22—H22	0.9500	C23A—H23A	0.9500
C23—C24	1.368 (13)	C24A—C25A	1.382 (15)
C23—H23	0.9500	C25A—C26A	1.384 (13)
C24—C25	1.389 (13)	C25A—H25A	0.9500
C25—C26	1.370 (12)	C26A—H26A	0.9500
C25—H25	0.9500	O1W—H1W1	0.8401
C26—H26	0.9500	O1W—H1W2	0.8424
Br1A—C12A	1.923 (7)	O1WA—H1W3	0.8399
C1A—O1A	1.231 (10)	O1WA—H1W4	0.8400
C15—O2—C17	116.9 (6)	O1A—C1A—C11A	119.5 (7)
C1—N1—N2	116.9 (6)	N1A—C1A—C11A	116.8 (7)
C1—N1—H1	121.6	C15A—O2A—C17A	117.5 (7)
N2—N1—H1	121.6	C1A—N1A—N2A	118.3 (7)
C2—N2—N1	115.4 (7)	C1A—N1A—H1A	120.8
O1—C1—N1	124.3 (7)	N2A—N1A—H1A	120.8
O1—C1—C11	122.1 (7)	C2A—N2A—N1A	116.4 (7)
N1—C1—C11	113.6 (6)	N2A—C2A—C21A	120.1 (7)
N2—C2—C21	120.6 (8)	N2A—C2A—H2A	120.0
N2—C2—H2	119.7	C21A—C2A—H2A	120.0
C21—C2—H2	119.7	C12A—C11A—C16A	117.0 (7)
C12—C11—C16	119.2 (7)	C12A—C11A—C1A	126.2 (7)
C12—C11—C1	122.1 (7)	C16A—C11A—C1A	116.1 (6)
C16—C11—C1	118.6 (6)	C13A—C12A—C11A	122.4 (7)
C11—C12—C13	121.0 (7)	C13A—C12A—Br1A	115.8 (6)
C11—C12—Br1	122.9 (6)	C11A—C12A—Br1A	121.7 (6)
C13—C12—Br1	116.0 (6)	C12A—C13A—C14A	119.4 (8)
C14—C13—C12	118.2 (7)	C12A—C13A—H13A	120.3
C14—C13—H13	120.9	C14A—C13A—H13A	120.3
C12—C13—H13	120.9	C15A—C14A—C13A	120.4 (8)
C13—C14—C15	121.9 (7)	C15A—C14A—H14A	119.8
C13—C14—H14	119.0	C13A—C14A—H14A	119.8
C15—C14—H14	119.0	O2A—C15A—C14A	116.1 (8)
O2—C15—C16	124.6 (7)	O2A—C15A—C16A	123.4 (7)
O2—C15—C14	116.2 (7)	C14A—C15A—C16A	120.4 (8)
C16—C15—C14	119.2 (7)	C15A—C16A—C11A	120.3 (7)
C15—C16—C11	120.4 (7)	C15A—C16A—H16A	119.9
C15—C16—H16	119.8	C11A—C16A—H16A	119.9
C11—C16—H16	119.8	O2A—C17A—H17D	109.5
O2—C17—H17A	109.5	O2A—C17A—H17E	109.5
O2—C17—H17B	109.5	H17D—C17A—H17E	109.5
H17A—C17—H17B	109.5	O2A—C17A—H17F	109.5
O2—C17—H17C	109.5	H17D—C17A—H17F	109.5
H17A—C17—H17C	109.5	H17E—C17A—H17F	109.5
H17B—C17—H17C	109.5	C22A—C21A—C26A	120.3 (8)
C26—C21—C22	118.6 (7)	C22A—C21A—C2A	119.2 (8)
C26—C21—C2	122.6 (7)	C26A—C21A—C2A	120.5 (7)
C22—C21—C2	118.7 (8)	C21A—C22A—C23A	120.0 (9)
C23—C22—C21	120.4 (8)	C21A—C22A—H22A	120.0
C23—C22—H22	119.8	C23A—C22A—H22A	120.0
C21—C22—H22	119.8	C24A—C23A—C22A	117.8 (9)
C24—C23—C22	117.5 (8)	C24A—C23A—H23A	121.1
C24—C23—H23	121.3	C22A—C23A—H23A	121.1
C22—C23—H23	121.3	F1A—C24A—C23A	118.1 (9)
F1—C24—C23	117.7 (8)	F1A—C24A—C25A	117.9 (9)
F1—C24—C25	117.9 (8)	C23A—C24A—C25A	123.9 (9)
C23—C24—C25	124.3 (8)	C24A—C25A—C26A	118.1 (9)
C26—C25—C24	117.7 (8)	C24A—C25A—H25A	121.0
C26—C25—H25	121.1	C26A—C25A—H25A	121.0
C24—C25—H25	121.1	C25A—C26A—C21A	119.9 (8)
C25—C26—C21	121.5 (7)	C25A—C26A—H26A	120.0
C25—C26—H26	119.3	C21A—C26A—H26A	120.0
C21—C26—H26	119.3	H1W1—O1W—H1W2	85.1
O1A—C1A—N1A	123.6 (8)	H1W3—O1WA—H1W4	85.2
C1—N1—N2—C2	169.4 (7)	O1A—C1A—N1A—N2A	8.9 (12)
N2—N1—C1—O1	2.2 (11)	C11A—C1A—N1A—N2A	−169.1 (6)
N2—N1—C1—C11	−179.1 (6)	C1A—N1A—N2A—C2A	173.4 (7)
N1—N2—C2—C21	−175.2 (6)	N1A—N2A—C2A—C21A	−177.9 (7)
O1—C1—C11—C12	−45.4 (10)	O1A—C1A—C11A—C12A	−130.6 (8)
N1—C1—C11—C12	135.9 (7)	N1A—C1A—C11A—C12A	47.4 (11)
O1—C1—C11—C16	130.4 (8)	O1A—C1A—C11A—C16A	39.6 (10)
N1—C1—C11—C16	−48.4 (9)	N1A—C1A—C11A—C16A	−142.4 (7)
C16—C11—C12—C13	−0.8 (10)	C16A—C11A—C12A—C13A	0.3 (11)
C1—C11—C12—C13	174.9 (7)	C1A—C11A—C12A—C13A	170.5 (7)
C16—C11—C12—Br1	174.6 (5)	C16A—C11A—C12A—Br1A	−177.3 (5)
C1—C11—C12—Br1	−9.7 (10)	C1A—C11A—C12A—Br1A	−7.1 (10)
C11—C12—C13—C14	−0.6 (11)	C11A—C12A—C13A—C14A	0.8 (12)
Br1—C12—C13—C14	−176.3 (6)	Br1A—C12A—C13A—C14A	178.5 (6)
C12—C13—C14—C15	2.8 (12)	C12A—C13A—C14A—C15A	−0.8 (12)
C17—O2—C15—C16	6.1 (12)	C17A—O2A—C15A—C14A	177.3 (7)
C17—O2—C15—C14	−174.6 (8)	C17A—O2A—C15A—C16A	−0.8 (11)
C13—C14—C15—O2	177.2 (7)	C13A—C14A—C15A—O2A	−178.6 (7)
C13—C14—C15—C16	−3.5 (13)	C13A—C14A—C15A—C16A	−0.4 (12)
O2—C15—C16—C11	−178.8 (7)	O2A—C15A—C16A—C11A	179.6 (7)
C14—C15—C16—C11	1.9 (12)	C14A—C15A—C16A—C11A	1.6 (11)
C12—C11—C16—C15	0.2 (11)	C12A—C11A—C16A—C15A	−1.6 (10)
C1—C11—C16—C15	−175.7 (7)	C1A—C11A—C16A—C15A	−172.7 (7)
N2—C2—C21—C26	−4.3 (12)	N2A—C2A—C21A—C22A	−174.8 (8)
N2—C2—C21—C22	171.0 (7)	N2A—C2A—C21A—C26A	5.4 (12)
C26—C21—C22—C23	1.4 (11)	C26A—C21A—C22A—C23A	−1.4 (12)
C2—C21—C22—C23	−174.1 (7)	C2A—C21A—C22A—C23A	178.8 (8)
C21—C22—C23—C24	−1.5 (12)	C21A—C22A—C23A—C24A	2.0 (13)
C22—C23—C24—F1	−179.8 (7)	C22A—C23A—C24A—F1A	179.4 (8)
C22—C23—C24—C25	−0.2 (13)	C22A—C23A—C24A—C25A	−3.1 (14)
F1—C24—C25—C26	−178.5 (7)	F1A—C24A—C25A—C26A	−179.1 (8)
C23—C24—C25—C26	1.9 (13)	C23A—C24A—C25A—C26A	3.3 (15)
C24—C25—C26—C21	−1.9 (12)	C24A—C25A—C26A—C21A	−2.4 (13)
C22—C21—C26—C25	0.4 (11)	C22A—C21A—C26A—C25A	1.6 (12)
C2—C21—C26—C25	175.7 (7)	C2A—C21A—C26A—C25A	−178.6 (8)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1···O1W	0.88	2.03	2.901 (9)	172
N1A—H1A···O1WA	0.88	2.01	2.860 (9)	163
O1W—H1W1···O1^i	0.84	1.99	2.832 (8)	180
O1W—H1W2···O1A^ii	0.84	2.01	2.856 (8)	180
O1WA—H1W3···O1^iii	0.84	2.06	2.897 (8)	180
O1WA—H1W4···O1A^iv	0.84	1.96	2.802 (7)	180

Symmetry codes: (i) x, −y+1, z−1/2; (ii) x+1/2, −y+1/2, z+1/2; (iii) x−1/2, −y+3/2, z−1/2; (iv) x, −y+1, z+1/2.