Bis(4-ethyl­anilinium) 4,5-dichloro­phthalate

The crystal structure of the title compound, 2C₈H₁₂N⁺·C₈H₃Cl₂O₄²⁻, is stabilized by nine N—H...O and four C—H...O hydrogen bonds, and also by C—H...π inter­actions. Intra­molecular C—H...O hydrogen bonds form C(6) chains along the c axis. This chain and the other hydrogen bonds generate edge-fused [R₁²(6)R₁²(4)R₄³(10)R₁²(4)R₃²(9)] motifs in a three-dimensional network. The dihedral angles between the carboxylate anion and the cation aromatic ring planes are 75.90 (2) and 68.15 (2)°, and the dihedral angles between the carboxyl­ate groups and the anion aromatic ring plane are 13.72 (3) and 84.64 (3)°.

Key indicators

• Single-crystal X-ray study
• T = 296 K
• Mean [sigma](C-C) = 0.005 Å
• R factor = 0.052
• wR factor = 0.145
• Data-to-parameter ratio = 14.6

checkCIF/PLATON results

No syntax errors found



Alert level B
PLAT222_ALERT_3_B Large Non-Solvent    H     Ueq(max)/Ueq(min) ...       4.24 Ratio
PLAT230_ALERT_2_B Hirshfeld Test Diff for    C10    -   C11     ..       8.79 su
PLAT230_ALERT_2_B Hirshfeld Test Diff for    C11    -   C16     ..       8.59 su
PLAT417_ALERT_2_B Short Inter D-H..H-D       H1     ..  H1C     ..       1.47 Ang.

Alert level C
PLAT042_ALERT_1_C Calc. and Rep. MoietyFormula Strings Differ ....          ?
PLAT063_ALERT_3_C Crystal Probably too Large for Beam Size .......       0.78 mm
PLAT094_ALERT_2_C Ratio of Maximum / Minimum Residual Density ....       2.17
PLAT152_ALERT_1_C Supplied and Calc Volume s.u. Inconsistent .....          ?
PLAT220_ALERT_2_C Large Non-Solvent    C     Ueq(max)/Ueq(min) ...       3.30 Ratio
PLAT230_ALERT_2_C Hirshfeld Test Diff for    C11    -   C12     ..       5.61 su
PLAT242_ALERT_2_C Check Low       Ueq as Compared to Neighbors for        C11
PLAT242_ALERT_2_C Check Low       Ueq as Compared to Neighbors for        C19
PLAT340_ALERT_3_C Low Bond Precision on C-C Bonds (x 1000) Ang ...          5
PLAT360_ALERT_2_C Short  C(sp3)-C(sp3) Bond  C10    -   C26    ...       1.34 Ang.
PLAT480_ALERT_4_C Long H...A H-Bond Reported H1B    ..  O1      ..       2.67 Ang.
PLAT480_ALERT_4_C Long H...A H-Bond Reported H23    ..  O3      ..       2.93 Ang.

Alert level G
FORMU01_ALERT_1_G  There is a discrepancy between the atom counts in the
            _chemical_formula_sum and _chemical_formula_moiety. This is
            usually due to the moiety formula being in the wrong format.
            Atom count from _chemical_formula_sum:   C24 H27 Cl2 N2 O4
            Atom count from _chemical_formula_moiety:C22 H17 Cl2 F6 O4
PLAT860_ALERT_3_G Note: Number of Least-Squares Restraints .......          3

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

   3 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
   9 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
   0 ALERT type 5 Informative message, check

---

S1. Comment

We have been interested in hydrogen-bonding systems formed by organic amines and carboxylic acids (Odabaşoğlu & Büyükgüngör, 2007a-c; 2006a-d; Temel et al., 2007; Odabaşoğlu et al., 2003; Büyükgüngör & Odabaşoğlu, 2006a,b; Büyükgüngör & Odabaşoğlu, 2003; Büyükgüngör & Odabaşoğlu, 2002; Ersanlı et al., 2004; Bozkurt et al., 2006; Yeşilel et al., 2006). The present work is part of a structural study of compounds of organic ammonium systems with hydrogen and halogen-bond donors and we report here the molecular and supramolecular structure of (I) (Figure 1).

In the phthalate anion, O1—C1—O2—C2 and O3—C8—O4—C7 planes and the plane of C2–C7 ring are not the same plane. The dihedral angles between the C2–C7 ring and O1—C1—O2—C2, O3—C8—O4—C7 planes are 13.72 (3)° and 84,64 (3)°, respectively. The dihedral angles between the aromatic C2–C7 (A), C11–C16 (B) and C19–C24 (C) rings planes are 75.90 (2)° (A/B), 68.15 (2)° (A/C), and 9.01 (2)° (B/C).

The ions are linked to each other by C6—H6···O1 hydrogen bonds forming C(6) chain along the z-axis (Fig. 2). Other hydrogen bons form [R₁²(6)R₁²(4)R₄³(10)R₁²(4)R₃²(9)] (Etter, 1990) motifs (Fig. 3). The C—H···π interaction and hydrogen bonds properties are given in Table1.

Related literature

For related literature, see: Bozkurt et al. (2006); Braga et al. (2002); Büyükgüngör & Odabaşoğlu (2002); Büyükgüngör & Odabaşoğlu (2003); Büyükgüngör & Odabaşoǧlu (2006a,b); Ersanlı et al. (2004); Etter (1990); Goswami et al. (1998); Goswami & Ghosh (1997); Joesten & Schaad (1974); Lam & Mak (2000); Mulliken & Person (1969); Odabaşoǧlu & Büyükgüngör (2006a,b,c,d); Odabaşoğlu & Büyükgüngör (2007a,b,c); Odabaşoğlu et al. (2003a,b); Pimentel & McClellan (1960); Scheiner (1997a); Scheiner (1997b); Temel et al. (2007); Yeşilel et al. (2006)..

S2. Experimental

The title compound was prepared according to the method described by Odabaşoğlu & Büyükgüngör (2007c), using 3-ethylaniline and 4,5-dichlorophthalic acid as starting materials (yield 95%; m.p. 458–459 K). Crystals of (I) suitable for X-ray analysis were obtained by slow evaporation of an ethanol-water (1:1) solution at room temperature.

S3. Refinement

All H atoms except bounded to N were refined using the riding model approximation with d(C—H) = 0.93 for aromatic, d(C—H) = 0.97 for methylene, d(C—H) = 0.96 for methyl and d(C—O) = 0.82 for hydroxyl H. (U_iso(H) = (1.2–1.5)U_eq(parent atom)]. N-bound H atoms were located in Fourier difference map and refined freely.

Computing details

Data collection: X-AREA (Stoe & Cie, 2002); cell refinement: X-AREA (Stoe & Cie, 2002); data reduction: X-RED32 (Stoe & Cie, 2002); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997); software used to prepare material for publication: WinGX (Farrugia, 1999).

Figures

	Fig. 1. A view of (I) with the atomic numbering scheme. Displacement ellipsoids are drawn at the 30% probability level..
	Fig. 2. Part of the crystal structure of (I), showing the C(6) chain along the c axis. H atoms not involved in hydrogen bonds have been omitted for clarity. [Symmetry codes: (i) 1 - x, 1 - y, 1 - z; (ii) x, 3/2 - y, 1 - z].
	Fig. 3. Part of the crystal structure of (I), showing the hydrogen bonding R1^2(6)R1^2(4)R4^3(10) R1^2(4)R3^2(9) motif. H atoms not involved in hydrogen bonds have been omitted for clarity.

Bis(4-ethylanilinium) 4,5-dichlorophthalate

Crystal data

2C7H7F3N^+·C8H3Cl2O4^2^−	F(000) = 1004
Mr = 478.38	Dx = 1.364 Mg m^−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 16318 reflections
a = 16.9642 (16) Å	θ = 2.1–27.9°
b = 11.8744 (8) Å	µ = 0.31 mm^−1
c = 11.8783 (11) Å	T = 296 K
β = 103.133 (8)°	Prism, colourless
V = 2330.2 (3) Å^3	0.78 × 0.45 × 0.23 mm
Z = 4

Data collection

Stoe IPDS2 diffractometer	4585 independent reflections
Radiation source: sealed X-ray tube, 12 x 0.4 mm long-fine focus	2666 reflections with I > 2σ(I)
Plane graphite monochromator	Rint = 0.069
Detector resolution: 6.67 pixels mm^-1	θmax = 26.0°, θmin = 2.1°
ω scans	h = −20→20
Absorption correction: integration (X-RED32; Stoe & Cie, 2002)	k = −14→14
Tmin = 0.828, Tmax = 0.932	l = −14→14
16318 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)] = 0.052	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.145	H atoms treated by a mixture of independent and constrained refinement
S = 0.92	w = 1/[σ^2(Fo^2) + (0.0797P)^2] where P = (Fo^2 + 2Fc^2)/3
4585 reflections	(Δ/σ)max < 0.001
314 parameters	Δρmax = 0.62 e Å^−3
3 restraints	Δρmin = −0.29 e Å^−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
C1	0.89830 (17)	0.9151 (2)	0.7758 (2)	0.0419 (6)
C2	0.83587 (16)	0.8676 (2)	0.6751 (2)	0.0393 (6)
C3	0.75484 (17)	0.8843 (2)	0.6729 (2)	0.0446 (7)
H3	0.7405	0.9267	0.7310	0.054*
C4	0.69517 (16)	0.8395 (3)	0.5866 (2)	0.0468 (7)
C5	0.71630 (17)	0.7758 (3)	0.5007 (2)	0.0468 (7)
C6	0.79687 (17)	0.7593 (2)	0.5006 (2)	0.0452 (7)
H6	0.8107	0.7178	0.4415	0.054*
C7	0.85740 (16)	0.8040 (2)	0.5880 (2)	0.0386 (6)
C8	0.94313 (17)	0.7689 (3)	0.5895 (2)	0.0450 (7)
C10	0.3417 (3)	0.8015 (5)	0.3264 (6)	0.1243 (19)
H10A	0.3462	0.7593	0.2581	0.149*
H10B	0.3283	0.8787	0.3027	0.149*
C11	0.2713 (3)	0.7511 (3)	0.3748 (4)	0.0775 (11)
C12	0.1952 (3)	0.7812 (4)	0.3238 (4)	0.0795 (11)
H12	0.1865	0.8332	0.2637	0.095*
C13	0.1310 (2)	0.7375 (3)	0.3581 (3)	0.0655 (9)
H13	0.0788	0.7594	0.3215	0.079*
C14	0.14248 (18)	0.6603 (3)	0.4476 (2)	0.0470 (7)
C15	0.21790 (19)	0.6257 (3)	0.5022 (3)	0.0611 (9)
H15	0.2254	0.5734	0.5619	0.073*
C16	0.2846 (2)	0.6721 (4)	0.4650 (4)	0.0795 (11)
H16	0.3371	0.6502	0.5002	0.095*
C17	0.4675 (3)	0.4776 (5)	0.3165 (5)	0.1188 (18)
H17A	0.5224	0.4905	0.3111	0.178*
H17B	0.4594	0.3986	0.3264	0.178*
H17C	0.4570	0.5181	0.3814	0.178*
C18	0.4113 (2)	0.5174 (4)	0.2085 (4)	0.0857 (12)
H18A	0.4242	0.4774	0.1437	0.103*
H18B	0.4219	0.5967	0.1986	0.103*
C19	0.3213 (2)	0.5033 (3)	0.2024 (3)	0.0582 (8)
C20	0.2659 (3)	0.5503 (3)	0.1126 (3)	0.0707 (10)
H20	0.2844	0.5928	0.0581	0.085*
C21	0.1838 (2)	0.5367 (3)	0.1003 (3)	0.0666 (9)
H21	0.1476	0.5698	0.0386	0.080*
C22	0.15610 (18)	0.4730 (3)	0.1807 (3)	0.0490 (7)
C23	0.2101 (2)	0.4279 (3)	0.2713 (3)	0.0625 (9)
H23	0.1918	0.3866	0.3269	0.075*
C24	0.2915 (2)	0.4426 (3)	0.2815 (3)	0.0661 (9)
H24	0.3276	0.4105	0.3440	0.079*
C26	0.4134 (4)	0.8002 (7)	0.4016 (6)	0.155 (3)
H26A	0.4537	0.8321	0.3661	0.233*
H26B	0.4278	0.7240	0.4243	0.233*
H26C	0.4101	0.8437	0.4685	0.233*
N1	0.07153 (15)	0.6147 (3)	0.4812 (2)	0.0472 (6)
N2	0.07019 (19)	0.4498 (3)	0.1670 (3)	0.0636 (8)
O1	0.87227 (13)	0.9484 (2)	0.86003 (19)	0.0649 (6)
H1	0.9093	0.9490	0.9180	0.097*
O2	0.97009 (11)	0.91689 (17)	0.76807 (17)	0.0506 (5)
O3	0.96912 (12)	0.68350 (18)	0.64711 (18)	0.0552 (5)
O4	0.98173 (12)	0.8219 (2)	0.52755 (18)	0.0606 (6)
Cl1	0.59467 (5)	0.86080 (9)	0.58955 (8)	0.0726 (3)
Cl2	0.64334 (5)	0.71200 (9)	0.39448 (7)	0.0705 (3)
H1A	0.048 (3)	0.671 (4)	0.521 (4)	0.094 (14)*
H1B	0.032 (2)	0.592 (3)	0.410 (3)	0.059 (9)*
H1C	0.085 (2)	0.562 (3)	0.531 (3)	0.055 (10)*
H2A	0.061 (3)	0.405 (4)	0.233 (4)	0.099 (15)*
H2B	0.053 (2)	0.412 (3)	0.099 (3)	0.064 (10)*
H2C	0.042 (3)	0.508 (4)	0.154 (4)	0.094 (16)*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
C1	0.0444 (16)	0.0418 (15)	0.0400 (15)	−0.0017 (13)	0.0109 (13)	0.0024 (12)
C2	0.0373 (14)	0.0427 (15)	0.0385 (14)	0.0007 (12)	0.0098 (11)	0.0037 (12)
C3	0.0404 (14)	0.0529 (17)	0.0413 (15)	0.0054 (13)	0.0107 (12)	−0.0009 (13)
C4	0.0346 (14)	0.0601 (18)	0.0463 (16)	0.0020 (13)	0.0102 (12)	0.0059 (14)
C5	0.0408 (15)	0.0549 (18)	0.0423 (15)	−0.0059 (13)	0.0042 (12)	0.0019 (14)
C6	0.0464 (16)	0.0531 (17)	0.0375 (14)	−0.0001 (13)	0.0123 (13)	−0.0009 (13)
C7	0.0379 (13)	0.0425 (15)	0.0366 (13)	0.0008 (12)	0.0114 (11)	0.0029 (12)
C8	0.0418 (15)	0.0593 (19)	0.0337 (14)	0.0011 (14)	0.0085 (12)	−0.0067 (14)
C10	0.090 (4)	0.117 (4)	0.173 (6)	−0.019 (3)	0.043 (4)	−0.026 (4)
C11	0.097 (3)	0.066 (2)	0.084 (3)	−0.027 (2)	0.052 (2)	−0.018 (2)
C12	0.091 (3)	0.080 (3)	0.073 (2)	−0.017 (2)	0.029 (2)	0.003 (2)
C13	0.069 (2)	0.069 (2)	0.059 (2)	−0.0064 (18)	0.0153 (17)	0.0029 (17)
C14	0.0458 (16)	0.0553 (18)	0.0421 (15)	−0.0014 (13)	0.0148 (13)	−0.0089 (14)
C15	0.0466 (18)	0.070 (2)	0.069 (2)	0.0003 (16)	0.0174 (16)	−0.0007 (18)
C16	0.0445 (18)	0.088 (3)	0.109 (3)	−0.0009 (18)	0.022 (2)	−0.025 (2)
C17	0.064 (3)	0.145 (5)	0.139 (5)	−0.011 (3)	0.005 (3)	−0.013 (4)
C18	0.070 (3)	0.091 (3)	0.099 (3)	−0.014 (2)	0.026 (2)	−0.016 (2)
C19	0.059 (2)	0.0532 (19)	0.064 (2)	−0.0058 (16)	0.0174 (17)	−0.0085 (17)
C20	0.087 (3)	0.064 (2)	0.066 (2)	−0.007 (2)	0.028 (2)	0.0127 (18)
C21	0.074 (2)	0.064 (2)	0.059 (2)	0.0117 (18)	0.0100 (18)	0.0138 (17)
C22	0.0506 (17)	0.0477 (17)	0.0496 (17)	0.0036 (14)	0.0131 (14)	−0.0100 (14)
C23	0.065 (2)	0.068 (2)	0.0549 (19)	−0.0063 (17)	0.0145 (17)	0.0163 (17)
C24	0.058 (2)	0.071 (2)	0.065 (2)	−0.0010 (18)	0.0043 (17)	0.0144 (18)
C26	0.106 (5)	0.217 (8)	0.144 (5)	−0.024 (5)	0.030 (4)	−0.011 (5)
N1	0.0397 (13)	0.0626 (18)	0.0404 (14)	0.0060 (13)	0.0112 (12)	0.0018 (14)
N2	0.0565 (18)	0.069 (2)	0.065 (2)	0.0073 (16)	0.0134 (16)	−0.0157 (18)
O1	0.0560 (13)	0.0947 (18)	0.0461 (12)	−0.0116 (13)	0.0156 (11)	−0.0244 (12)
O2	0.0368 (11)	0.0623 (13)	0.0521 (12)	−0.0064 (9)	0.0091 (9)	−0.0079 (10)
O3	0.0502 (12)	0.0549 (13)	0.0599 (13)	0.0133 (10)	0.0112 (10)	0.0027 (11)
O4	0.0424 (11)	0.0909 (17)	0.0525 (12)	0.0032 (11)	0.0194 (10)	0.0124 (12)
Cl1	0.0358 (4)	0.1121 (8)	0.0693 (6)	0.0081 (4)	0.0108 (4)	0.0000 (5)
Cl2	0.0515 (5)	0.0935 (7)	0.0599 (5)	−0.0144 (4)	−0.0014 (4)	−0.0156 (5)

Geometric parameters (Å, º)

C1—O2	1.242 (3)	C16—H16	0.9300
C1—O1	1.246 (3)	C17—C18	1.491 (7)
C1—C2	1.514 (4)	C17—H17A	0.9600
C2—C3	1.383 (4)	C17—H17B	0.9600
C2—C7	1.395 (4)	C17—H17C	0.9600
C3—C4	1.374 (4)	C18—C19	1.521 (5)
C3—H3	0.9300	C18—H18A	0.9700
C4—C5	1.381 (4)	C18—H18B	0.9700
C4—Cl1	1.732 (3)	C19—C20	1.370 (5)
C5—C6	1.381 (4)	C19—C24	1.370 (5)
C5—Cl2	1.729 (3)	C20—C21	1.376 (5)
C6—C7	1.389 (4)	C20—H20	0.9300
C6—H6	0.9300	C21—C22	1.382 (5)
C7—C8	1.509 (4)	C21—H21	0.9300
C8—O3	1.246 (3)	C22—C23	1.356 (4)
C8—O4	1.260 (4)	C22—N2	1.456 (4)
C10—C26	1.335 (8)	C23—C24	1.370 (5)
C10—C11	1.557 (7)	C23—H23	0.9300
C10—H10A	0.9700	C24—H24	0.9300
C10—H10B	0.9700	C26—H26A	0.9600
C11—C12	1.345 (6)	C26—H26B	0.9600
C11—C16	1.403 (6)	C26—H26C	0.9600
C12—C13	1.350 (5)	N1—H1A	0.96 (5)
C12—H12	0.9300	N1—H1B	0.99 (3)
C13—C14	1.383 (5)	N1—H1C	0.86 (4)
C13—H13	0.9300	N2—H2A	0.98 (5)
C14—C15	1.360 (4)	N2—H2B	0.91 (4)
C14—N1	1.456 (4)	N2—H2C	0.84 (5)
C15—C16	1.417 (5)	O1—H1	0.8200
C15—H15	0.9300
O2—C1—O1	125.9 (3)	C18—C17—H17B	109.5
O2—C1—C2	118.0 (2)	H17A—C17—H17B	109.5
O1—C1—C2	116.1 (3)	C18—C17—H17C	109.5
C3—C2—C7	119.3 (2)	H17A—C17—H17C	109.5
C3—C2—C1	118.4 (2)	H17B—C17—H17C	109.5
C7—C2—C1	122.2 (2)	C17—C18—C19	116.4 (4)
C4—C3—C2	121.3 (3)	C17—C18—H18A	108.2
C4—C3—H3	119.4	C19—C18—H18A	108.2
C2—C3—H3	119.4	C17—C18—H18B	108.2
C3—C4—C5	119.5 (3)	C19—C18—H18B	108.2
C3—C4—Cl1	119.3 (2)	H18A—C18—H18B	107.3
C5—C4—Cl1	121.1 (2)	C20—C19—C24	117.0 (3)
C4—C5—C6	120.1 (2)	C20—C19—C18	119.8 (3)
C4—C5—Cl2	121.1 (2)	C24—C19—C18	123.3 (3)
C6—C5—Cl2	118.8 (2)	C19—C20—C21	122.3 (3)
C5—C6—C7	120.6 (3)	C19—C20—H20	118.9
C5—C6—H6	119.7	C21—C20—H20	118.9
C7—C6—H6	119.7	C20—C21—C22	119.1 (3)
C6—C7—C2	119.2 (3)	C20—C21—H21	120.5
C6—C7—C8	116.7 (2)	C22—C21—H21	120.5
C2—C7—C8	123.7 (2)	C23—C22—C21	119.4 (3)
O3—C8—O4	124.2 (3)	C23—C22—N2	119.5 (3)
O3—C8—C7	116.8 (3)	C21—C22—N2	121.1 (3)
O4—C8—C7	118.8 (3)	C22—C23—C24	120.4 (3)
C26—C10—C11	114.0 (6)	C22—C23—H23	119.8
C26—C10—H10A	108.8	C24—C23—H23	119.8
C11—C10—H10A	108.8	C23—C24—C19	121.9 (3)
C26—C10—H10B	108.8	C23—C24—H24	119.0
C11—C10—H10B	108.8	C19—C24—H24	119.0
H10A—C10—H10B	107.7	C10—C26—H26A	109.5
C12—C11—C16	119.5 (4)	C10—C26—H26B	109.5
C12—C11—C10	118.0 (5)	H26A—C26—H26B	109.5
C16—C11—C10	122.4 (5)	C10—C26—H26C	109.5
C11—C12—C13	121.4 (4)	H26A—C26—H26C	109.5
C11—C12—H12	119.3	H26B—C26—H26C	109.5
C13—C12—H12	119.3	C14—N1—H1A	110 (2)
C12—C13—C14	120.2 (4)	C14—N1—H1B	107.7 (19)
C12—C13—H13	119.9	H1A—N1—H1B	109 (3)
C14—C13—H13	119.9	C14—N1—H1C	111 (2)
C15—C14—C13	121.3 (3)	H1A—N1—H1C	104 (3)
C15—C14—N1	120.2 (3)	H1B—N1—H1C	115 (3)
C13—C14—N1	118.4 (3)	C22—N2—H2A	110 (3)
C14—C15—C16	117.7 (3)	C22—N2—H2B	107 (2)
C14—C15—H15	121.1	H2A—N2—H2B	112 (3)
C16—C15—H15	121.1	C22—N2—H2C	112 (3)
C11—C16—C15	119.8 (4)	H2A—N2—H2C	114 (4)
C11—C16—H16	120.1	H2B—N2—H2C	100 (4)
C15—C16—H16	120.1	C1—O1—H1	109.5
C18—C17—H17A	109.5
O2—C1—C2—C3	−168.0 (3)	C26—C10—C11—C12	158.2 (6)
O1—C1—C2—C3	12.5 (4)	C26—C10—C11—C16	−25.0 (8)
O2—C1—C2—C7	14.8 (4)	C16—C11—C12—C13	0.4 (6)
O1—C1—C2—C7	−164.7 (3)	C10—C11—C12—C13	177.4 (4)
C7—C2—C3—C4	0.0 (4)	C11—C12—C13—C14	0.2 (6)
C1—C2—C3—C4	−177.3 (3)	C12—C13—C14—C15	−0.7 (5)
C2—C3—C4—C5	0.5 (4)	C12—C13—C14—N1	−179.5 (3)
C2—C3—C4—Cl1	178.8 (2)	C13—C14—C15—C16	0.5 (5)
C3—C4—C5—C6	−1.2 (4)	N1—C14—C15—C16	179.3 (3)
Cl1—C4—C5—C6	−179.5 (2)	C12—C11—C16—C15	−0.6 (6)
C3—C4—C5—Cl2	176.8 (2)	C10—C11—C16—C15	−177.4 (4)
Cl1—C4—C5—Cl2	−1.6 (4)	C14—C15—C16—C11	0.1 (5)
C4—C5—C6—C7	1.6 (4)	C17—C18—C19—C20	171.9 (4)
Cl2—C5—C6—C7	−176.5 (2)	C17—C18—C19—C24	−9.8 (6)
C5—C6—C7—C2	−1.1 (4)	C24—C19—C20—C21	−0.9 (6)
C5—C6—C7—C8	172.1 (3)	C18—C19—C20—C21	177.5 (4)
C3—C2—C7—C6	0.4 (4)	C19—C20—C21—C22	−0.3 (6)
C1—C2—C7—C6	177.5 (2)	C20—C21—C22—C23	1.6 (5)
C3—C2—C7—C8	−172.4 (3)	C20—C21—C22—N2	−175.7 (3)
C1—C2—C7—C8	4.7 (4)	C21—C22—C23—C24	−1.7 (5)
C6—C7—C8—O3	−90.4 (3)	N2—C22—C23—C24	175.7 (3)
C2—C7—C8—O3	82.5 (3)	C22—C23—C24—C19	0.5 (6)
C6—C7—C8—O4	85.0 (3)	C20—C19—C24—C23	0.8 (5)
C2—C7—C8—O4	−102.1 (3)	C18—C19—C24—C23	−177.5 (4)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1B···O1^i	0.99 (4)	2.67 (3)	3.442 (3)	134 (2)
N1—H1C···O1^ii	0.86 (4)	1.90 (4)	2.747 (4)	172 (3)
N1—H1B···O2^i	0.99 (4)	1.77 (4)	2.746 (3)	166 (3)
N1—H1A···O3^iii	0.93 (4)	2.24 (4)	3.021 (3)	140 (3)
N1—H1A···O4^iii	0.93 (4)	2.15 (4)	3.013 (4)	154 (3)
N2—H2C···O2^i	0.84 (5)	2.20 (5)	2.784 (4)	126 (4)
N2—H2A···O3^iv	0.98 (5)	1.94 (5)	2.913 (5)	174 (4)
N2—H2C···O4^i	0.84 (5)	2.58 (5)	3.350 (5)	152 (4)
N2—H2B···O4^v	0.92 (4)	1.83 (4)	2.739 (4)	172 (3)
C6—H6···O1^vi	0.93	2.52	3.388 (3)	154
C13—H13···O3^i	0.93	2.54	3.402 (4)	154
C15—H15···O1^ii	0.93	2.55	3.254 (4)	133
C23—H23···O3^iv	0.93	2.93	3.641 (4)	134
C23—H23···Cg1	0.93	2.69	3.389 (4)	133

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