Methyl 4-chloro-3,5-di-p-tolyl-1H-pyrrole-2-carboxyl­ate dichloro­methane hemisolvate

The structure of the title compound, C₂₀H₁₈ClNO₂·0.5CH₂Cl₂, at 173 K is described. There is one crystallographically distinct mol­ecule which forms centrosymmetric dimers through N—H...O hydrogen bonding. The dichloro­methane solvent mol­ecule is disordered across an inversion centre.

Key indicators

• Single-crystal X-ray study
• T = 173 K
• Mean [sigma](C-C) = 0.004 Å
• Disorder in solvent or counterion
• R factor = 0.051
• wR factor = 0.156
• Data-to-parameter ratio = 13.4

checkCIF/PLATON results

No syntax errors found



Alert level B
PLAT148_ALERT_3_B su on the      b  - Axis is Too Large (x 1000) .         11 Ang.
PLAT149_ALERT_3_B su on the  gamma   Angle is Too Large (x 100) ..          7 Deg.

Alert level C
PLAT041_ALERT_1_C Calc. and Rep. SumFormula Strings    Differ ....          ?
PLAT042_ALERT_1_C Calc. and Rep. MoietyFormula Strings Differ ....          ?
PLAT045_ALERT_1_C Calculated and Reported Z Differ by ............       0.50 Ratio
PLAT244_ALERT_4_C Low   'Solvent' Ueq as Compared to Neighbors for        C21
PLAT302_ALERT_4_C Anion/Solvent Disorder .........................      50.00 Perc.

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

   3 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
   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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Computing details

Data collection: CAD-4 EXPRESS (Enraf–Nonius, 1994); cell refinement: CAD-4 EXPRESS; data reduction: XCAD4 (Harms & Wocadlo, 1995); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: X-SEED (Barbour, 2001) and ORTEP-3 (Farrugia, 1997); software used to prepare material for publication: WinGX (Farrugia, 1999).

Methyl 4-chloro-3,5-di-p-tolyl-1H-pyrrole-2-carboxylate dichloromethane hemisolvate

Crystal data

C20H18ClNO2·0.5CH2Cl2	Z = 2
Mr = 382.27	F(000) = 398
Triclinic, P1	Dx = 1.350 Mg m^−3
Hall symbol: -P 1	Melting point = 452–458 K
a = 8.456 (3) Å	Mo Kα radiation, λ = 0.71073 Å
b = 9.902 (11) Å	Cell parameters from 25 reflections
c = 12.316 (3) Å	θ = 9.6–14.1°
α = 71.61 (5)°	µ = 0.36 mm^−1
β = 82.94 (3)°	T = 173 K
γ = 74.33 (7)°	Plate, colourless
V = 941.4 (11) Å^3	0.45 × 0.40 × 0.30 mm

Data collection

Enraf–Nonius TurboCAD-4 diffractometer	Rint = 0.049
Radiation source: fine-focus sealed tube	θmax = 25.0°, θmin = 1.7°
Graphite monochromator	h = −9→10
non–profiled ω/2θ scans	k = −11→11
3482 measured reflections	l = 0→14
3314 independent reflections	3 standard reflections every 60 min
2791 reflections with I > 2σ(I)	intensity decay: 5%

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)] = 0.051	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.156	H-atom parameters constrained
S = 1.05	w = 1/[σ^2(Fo^2) + (0.0933P)^2 + 0.75P] where P = (Fo^2 + 2Fc^2)/3
3314 reflections	(Δ/σ)max < 0.001
247 parameters	Δρmax = 0.36 e Å^−3
0 restraints	Δρmin = −0.48 e Å^−3

Special details

Experimental. Iodine (1.28 g, 10.02 mmol) was added to a mixture of methyl 4-chloro-1H-pyrrole-2-carboxylate (0.80 g, 5.01 mmol) and silver trifluoroacetate (2.21 g, 10.02 mmol) in chloroform (20 ml) at 273 K (ice bath) under a nitrogen atmosphere. The reaction mixture was stirred at room temperature for 7 h with exclusion of light, before quenching with aqueous sodium sulfite and brine solution. The reaction mixture was extracted with ethyl acetate (3 × 20 ml), and the combined organic extracts were dried and filtered through a small plug of silica gel. The solution was concentrated under reduced pressure to give methyl 4-chloro-3,5-diiodo-1H-pyrrole-2-carboxylate (1.85 g, 90%) as a white solid (m.p. 465–470 K). Spectroscopic analysis: ¹H NMR (300 MHz, CDCl₃, δ, p.p.m.): 3.92 (3H, s), 9.69 (1H, bs); IR (Medium?, ν, cm^-1): 3242, 1681, 1445, 1391, 1238.

A solution of the diiodopyrrole from above (0.216 g, 0.525 mmol) in acetone (10 ml), p-tolylboronic acid (0.179 g, 1.313 mmol), 2M potassium carbonate (5 ml) and palladium acetate (0.020 g, 0.089 mmol) was refluxed overnight under an atmosphere of nitrogen. The reaction was cooled to room temperature, quenched by the addition of water (10 ml) and extracted with ethyl acetate (2 × 10 ml). The organic layer was dried and evaporated to give the crude product, which was purified by silica-gel chromatography (eluent 20% ethyl acetate–hexanes). The product was recrystallized from diethyl ether–hexane (1:4 v/v) to give the title compound, (I), in 78% yield as colourless crystals. Crystals of (I) suitable for X-ray analysis were obtained by recrystallization from dichloromethane (m.p. 452–458 K). Spectroscopic analysis: ¹H NMR (300 MHz, CDCl₃, δ, p.p.m.): 2.41 (6H, s), 3.73 (3H, s), 7.27 (6H, m), 7.64 (2H, m), 9.20 (1H, bs); ¹³C NMR (75 MHz, CDCl₃, δ, p.p.m.): 21.68, 21.74, 51.91, 127.28, 127.41, 128.38, 128.76, 129.38, 129.78, 129.93, 130.48, 130.72, 137.70, 138.93, 161.49; IR (Medium?, ν, cm^-1): 3288, 1676, 1450, 1292; MS m/z 341 (M⁺, ³⁷Cl, 20%), 339 (M⁺, ³⁵Cl, 55%), 309 (20%), 307 (60%), 244 (100%).

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.

Least-squares planes (x,y,z in crystal coordinates) and deviations from them (* indicates atom used to define plane)

4.2020 (0.0097) x + 7.8660 (0.0087) y - 2.9795 (0.0158) z = 6.1041 (0.0112)

* 0.0053 (0.0015) N1 * -0.0032 (0.0016) C1 * -0.0001 (0.0015) C2 * 0.0033 (0.0015) C3 * -0.0053 (0.0015) C4 - 0.0861 (0.0044) C5 0.0419 (0.0043) C7 - 0.0202 (0.0041) Cl1 - 0.1076 (0.0044) C14

Rms deviation of fitted atoms = 0.0039

0.5892 (0.0091) x - 2.8203 (0.0103) y + 10.0172 (0.0092) z = 0.4353 (0.0100)

Angle to previous plane (with approximate e.s.d.) = 46.78 (0.12)

* 0.0044 (0.0017) C7 * -0.0074 (0.0018) C8 * 0.0037 (0.0019) C9 * 0.0031 (0.0019) C10 * -0.0061 (0.0019) C11 * 0.0024 (0.0018) C12 - 0.0055 (0.0039) C2 0.0375 (0.0050) C13

Rms deviation of fitted atoms = 0.0048

3.4886 (0.0080) x + 9.7512 (0.0054) y + 2.9889 (0.0136) z = 9.4452 (0.0081)

Angle to previous plane (with approximate e.s.d.) = 70.64 (0.10)

* 0.0034 (0.0018) C14 * 0.0013 (0.0019) C15 * -0.0021 (0.0019) C16 * -0.0019 (0.0019) C17 * 0.0068 (0.0019) C18 * -0.0075 (0.0018) C19 - 0.0374 (0.0038) C4 - 0.0089 (0.0046) C20

Rms deviation of fitted atoms = 0.0045

4.4354 (0.0079) x + 6.9848 (0.0056) y - 4.3081 (0.0100) z = 4.8307 (0.0090)

Angle to previous plane (with approximate e.s.d.) = 37.24 (0.09)

* -0.1042 (0.0011) H1 * 0.0038 (0.0010) N1 * 0.1013 (0.0020) C1 * -0.0729 (0.0018) C5 * -0.0189 (0.0020) O2 * 0.1042 (0.0011) H1_$2 * -0.0038 (0.0010) N1_$2 * -0.1013 (0.0020) C1_$2 * 0.0729 (0.0018) C5_$2 * 0.0189 (0.0020) O2_$2

Rms deviation of fitted atoms = 0.0732

5.7205 (0.0088) x + 6.3705 (0.0109) y - 3.7855 (0.0170) z = 4.7726 (0.0155)

Angle to previous plane (with approximate e.s.d.) = 11.18 (0.19)

* -0.0022 (0.0006) C1 * 0.0075 (0.0021) C5 * -0.0024 (0.0007) O1 * -0.0029 (0.0008) O2 0.0201 (0.0048) C6 - 0.0603 (0.0053) H1_$2

Rms deviation of fitted atoms = 0.0043

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. All H atoms were calculated using the riding model of SHELXL. The dichloromethane solvent molecule contains a disorder about a inversion centre and was modeled with anisotropically refined carbon and chlorine atoms.

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

	x	y	z	Uiso*/Ueq	Occ. (<1)
Cl1	−0.00913 (7)	0.80466 (8)	0.06952 (5)	0.0334 (2)
O1	0.3575 (2)	0.7011 (2)	0.46000 (15)	0.0343 (4)
O2	0.1835 (2)	0.8887 (2)	0.51273 (17)	0.0426 (5)
N1	−0.0268 (3)	0.9212 (2)	0.34383 (18)	0.0291 (5)
H1	−0.0741	0.9671	0.3945	0.035*
C1	0.1325 (3)	0.8366 (3)	0.3481 (2)	0.0263 (5)
C2	0.1660 (3)	0.7834 (3)	0.2537 (2)	0.0255 (5)
C3	0.0179 (3)	0.8402 (3)	0.1937 (2)	0.0279 (5)
C4	−0.1012 (3)	0.9242 (3)	0.2504 (2)	0.0274 (5)
C5	0.2246 (3)	0.8146 (3)	0.4476 (2)	0.0275 (5)
C6	0.4588 (4)	0.6703 (4)	0.5553 (3)	0.0448 (7)
H6A	0.5245	0.7429	0.5381	0.067*
H6B	0.5321	0.5718	0.5684	0.067*
H6C	0.3886	0.6753	0.6242	0.067*
C7	0.3247 (3)	0.6910 (3)	0.2193 (2)	0.0258 (5)
C8	0.4724 (3)	0.7283 (3)	0.2200 (2)	0.0286 (5)
H8	0.4723	0.8121	0.2420	0.034*
C9	0.6204 (3)	0.6427 (3)	0.1883 (2)	0.0334 (6)
H9	0.7200	0.6685	0.1905	0.040*
C10	0.6259 (3)	0.5205 (3)	0.1535 (2)	0.0344 (6)
C11	0.4769 (3)	0.4858 (3)	0.1516 (2)	0.0348 (6)
H11	0.4760	0.4039	0.1274	0.042*
C12	0.3295 (3)	0.5700 (3)	0.1848 (2)	0.0322 (6)
H12	0.2299	0.5435	0.1836	0.039*
C13	0.7868 (4)	0.4264 (4)	0.1210 (3)	0.0536 (8)
H13A	0.8688	0.4847	0.0963	0.080*
H13B	0.7698	0.3913	0.0583	0.080*
H13C	0.8259	0.3421	0.1873	0.080*
C14	−0.2770 (3)	0.9975 (3)	0.2302 (2)	0.0259 (5)
C15	−0.3381 (3)	1.0526 (3)	0.1211 (2)	0.0332 (6)
H15	−0.2655	1.0465	0.0566	0.040*
C16	−0.5055 (3)	1.1170 (3)	0.1053 (2)	0.0352 (6)
H16	−0.5449	1.1539	0.0299	0.042*
C17	−0.6164 (3)	1.1283 (3)	0.1979 (2)	0.0322 (6)
C18	−0.5543 (3)	1.0736 (3)	0.3066 (2)	0.0332 (6)
H18	−0.6267	1.0815	0.3709	0.040*
C19	−0.3873 (3)	1.0073 (3)	0.3236 (2)	0.0317 (6)
H19	−0.3484	0.9684	0.3991	0.038*
C20	−0.7974 (4)	1.1977 (4)	0.1804 (3)	0.0464 (8)
H20A	−0.8492	1.1282	0.1657	0.070*
H20B	−0.8113	1.2867	0.1149	0.070*
H20C	−0.8491	1.2233	0.2493	0.070*
C21	−0.0720 (12)	0.5340 (11)	0.4882 (11)	0.086 (3)	0.50
H21A	−0.0955	0.6353	0.4354	0.104*	0.50
H21B	−0.1774	0.5093	0.5203	0.104*	0.50
Cl2	0.0530 (8)	0.5169 (8)	0.5978 (4)	0.155 (2)	0.50
Cl3	0.0446 (5)	0.4064 (5)	0.4155 (4)	0.1078 (14)	0.50

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
Cl1	0.0291 (3)	0.0534 (4)	0.0271 (3)	−0.0123 (3)	0.0011 (2)	−0.0239 (3)
O1	0.0335 (10)	0.0438 (11)	0.0287 (9)	−0.0024 (8)	−0.0070 (8)	−0.0189 (8)
O2	0.0353 (11)	0.0632 (13)	0.0403 (11)	−0.0037 (9)	−0.0051 (8)	−0.0364 (10)
N1	0.0249 (11)	0.0437 (12)	0.0264 (11)	−0.0095 (9)	0.0027 (8)	−0.0216 (10)
C1	0.0211 (12)	0.0351 (13)	0.0276 (12)	−0.0075 (10)	0.0010 (9)	−0.0164 (10)
C2	0.0239 (12)	0.0334 (13)	0.0247 (12)	−0.0115 (10)	0.0030 (9)	−0.0140 (10)
C3	0.0277 (12)	0.0428 (14)	0.0221 (12)	−0.0168 (11)	0.0038 (10)	−0.0170 (11)
C4	0.0236 (12)	0.0390 (14)	0.0255 (12)	−0.0123 (10)	0.0019 (9)	−0.0150 (10)
C5	0.0224 (12)	0.0372 (14)	0.0276 (12)	−0.0080 (10)	0.0032 (10)	−0.0173 (11)
C6	0.0451 (17)	0.0507 (18)	0.0399 (16)	−0.0017 (14)	−0.0186 (13)	−0.0174 (14)
C7	0.0225 (12)	0.0360 (13)	0.0202 (11)	−0.0094 (10)	0.0011 (9)	−0.0091 (10)
C8	0.0286 (13)	0.0353 (13)	0.0266 (12)	−0.0116 (11)	0.0022 (10)	−0.0136 (10)
C9	0.0240 (13)	0.0449 (15)	0.0322 (14)	−0.0105 (11)	0.0026 (10)	−0.0123 (12)
C10	0.0316 (14)	0.0432 (16)	0.0267 (13)	−0.0044 (12)	0.0035 (10)	−0.0138 (12)
C11	0.0407 (15)	0.0392 (15)	0.0306 (13)	−0.0100 (12)	0.0009 (11)	−0.0196 (12)
C12	0.0286 (13)	0.0462 (15)	0.0287 (13)	−0.0139 (11)	0.0011 (10)	−0.0176 (12)
C13	0.0383 (17)	0.067 (2)	0.055 (2)	0.0010 (15)	0.0058 (14)	−0.0306 (17)
C14	0.0224 (12)	0.0332 (13)	0.0283 (12)	−0.0105 (10)	0.0014 (10)	−0.0155 (10)
C15	0.0300 (13)	0.0450 (15)	0.0277 (13)	−0.0123 (12)	0.0035 (10)	−0.0143 (12)
C16	0.0348 (14)	0.0419 (15)	0.0301 (14)	−0.0082 (12)	−0.0065 (11)	−0.0111 (12)
C17	0.0260 (13)	0.0352 (14)	0.0402 (15)	−0.0069 (11)	−0.0030 (11)	−0.0180 (12)
C18	0.0261 (13)	0.0466 (16)	0.0365 (14)	−0.0122 (11)	0.0047 (11)	−0.0250 (12)
C19	0.0274 (13)	0.0487 (16)	0.0273 (13)	−0.0139 (11)	0.0006 (10)	−0.0194 (12)
C20	0.0286 (15)	0.0563 (19)	0.0565 (19)	−0.0022 (13)	−0.0101 (13)	−0.0235 (16)
C21	0.080 (6)	0.071 (6)	0.108 (8)	−0.033 (5)	0.009 (6)	−0.018 (6)
Cl2	0.191 (5)	0.235 (6)	0.072 (2)	−0.168 (5)	−0.011 (3)	0.006 (3)
Cl3	0.116 (3)	0.117 (3)	0.089 (3)	−0.048 (2)	0.049 (2)	−0.031 (2)

Geometric parameters (Å, º)

Cl1—C3	1.727 (2)	C11—C12	1.395 (4)
O1—C5	1.341 (3)	C11—H11	0.9500
O1—C6	1.444 (3)	C12—H12	0.9500
O2—C5	1.211 (3)	C13—H13A	0.9800
N1—C4	1.367 (3)	C13—H13B	0.9800
N1—C1	1.378 (3)	C13—H13C	0.9800
N1—H1	0.8800	C14—C15	1.388 (4)
C1—C2	1.390 (3)	C14—C19	1.399 (4)
C1—C5	1.460 (3)	C15—C16	1.396 (4)
C2—C3	1.420 (4)	C15—H15	0.9500
C2—C7	1.504 (4)	C16—C17	1.398 (4)
C3—C4	1.391 (4)	C16—H16	0.9500
C4—C14	1.480 (4)	C17—C18	1.387 (4)
C6—H6A	0.9800	C17—C20	1.510 (4)
C6—H6B	0.9800	C18—C19	1.398 (4)
C6—H6C	0.9800	C18—H18	0.9500
C7—C12	1.381 (4)	C19—H19	0.9500
C7—C8	1.397 (3)	C20—H20A	0.9800
C8—C9	1.397 (4)	C20—H20B	0.9800
C8—H8	0.9500	C20—H20C	0.9800
C9—C10	1.393 (4)	C21—Cl2	1.755 (13)
C9—H9	0.9500	C21—Cl3	1.787 (13)
C10—C11	1.398 (4)	C21—H21A	0.9900
C10—C13	1.516 (4)	C21—H21B	0.9900
C5—O1—C6	117.0 (2)	C7—C12—C11	121.6 (2)
C4—N1—C1	110.8 (2)	C7—C12—H12	119.2
C4—N1—H1	124.6	C11—C12—H12	119.2
C1—N1—H1	124.6	C10—C13—H13A	109.5
N1—C1—C2	108.7 (2)	C10—C13—H13B	109.5
N1—C1—C5	117.2 (2)	H13A—C13—H13B	109.5
C2—C1—C5	134.0 (2)	C10—C13—H13C	109.5
C1—C2—C3	104.7 (2)	H13A—C13—H13C	109.5
C1—C2—C7	128.2 (2)	H13B—C13—H13C	109.5
C3—C2—C7	127.1 (2)	C15—C14—C19	118.3 (2)
C4—C3—C2	110.5 (2)	C15—C14—C4	122.0 (2)
C4—C3—Cl1	125.5 (2)	C19—C14—C4	119.6 (2)
C2—C3—Cl1	123.97 (19)	C14—C15—C16	120.6 (2)
N1—C4—C3	105.3 (2)	C14—C15—H15	119.7
N1—C4—C14	122.0 (2)	C16—C15—H15	119.7
C3—C4—C14	132.6 (2)	C15—C16—C17	121.4 (2)
O2—C5—O1	124.0 (2)	C15—C16—H16	119.3
O2—C5—C1	123.6 (2)	C17—C16—H16	119.3
O1—C5—C1	112.3 (2)	C18—C17—C16	117.6 (2)
O1—C6—H6A	109.5	C18—C17—C20	121.1 (3)
O1—C6—H6B	109.5	C16—C17—C20	121.3 (3)
H6A—C6—H6B	109.5	C17—C18—C19	121.4 (2)
O1—C6—H6C	109.5	C17—C18—H18	119.3
H6A—C6—H6C	109.5	C19—C18—H18	119.3
H6B—C6—H6C	109.5	C18—C19—C14	120.6 (2)
C12—C7—C8	118.3 (2)	C18—C19—H19	119.7
C12—C7—C2	121.9 (2)	C14—C19—H19	119.7
C8—C7—C2	119.8 (2)	C17—C20—H20A	109.5
C7—C8—C9	120.1 (2)	C17—C20—H20B	109.5
C7—C8—H8	120.0	H20A—C20—H20B	109.5
C9—C8—H8	120.0	C17—C20—H20C	109.5
C10—C9—C8	121.9 (2)	H20A—C20—H20C	109.5
C10—C9—H9	119.1	H20B—C20—H20C	109.5
C8—C9—H9	119.1	Cl2—C21—Cl3	104.8 (5)
C9—C10—C11	117.4 (2)	Cl2—C21—H21A	110.8
C9—C10—C13	121.8 (3)	Cl3—C21—H21A	110.8
C11—C10—C13	120.8 (3)	Cl2—C21—H21B	110.8
C12—C11—C10	120.7 (2)	Cl3—C21—H21B	110.8
C12—C11—H11	119.6	H21A—C21—H21B	108.9
C10—C11—H11	119.6
C4—N1—C1—C2	0.9 (3)	C3—C2—C7—C8	131.1 (3)
C4—N1—C1—C5	−175.9 (2)	C12—C7—C8—C9	−1.2 (4)
N1—C1—C2—C3	−0.3 (3)	C2—C7—C8—C9	179.9 (2)
C5—C1—C2—C3	175.7 (3)	C7—C8—C9—C10	1.1 (4)
N1—C1—C2—C7	177.6 (2)	C8—C9—C10—C11	−0.1 (4)
C5—C1—C2—C7	−6.3 (5)	C8—C9—C10—C13	−179.0 (3)
C1—C2—C3—C4	−0.3 (3)	C9—C10—C11—C12	−0.8 (4)
C7—C2—C3—C4	−178.3 (2)	C13—C10—C11—C12	178.1 (3)
C1—C2—C3—Cl1	−178.87 (19)	C8—C7—C12—C11	0.2 (4)
C7—C2—C3—Cl1	3.1 (4)	C2—C7—C12—C11	179.1 (2)
C1—N1—C4—C3	−1.0 (3)	C10—C11—C12—C7	0.8 (4)
C1—N1—C4—C14	175.1 (2)	N1—C4—C14—C15	153.9 (3)
C2—C3—C4—N1	0.8 (3)	C3—C4—C14—C15	−31.2 (4)
Cl1—C3—C4—N1	179.35 (19)	N1—C4—C14—C19	−28.6 (4)
C2—C3—C4—C14	−174.7 (3)	C3—C4—C14—C19	146.3 (3)
Cl1—C3—C4—C14	3.9 (4)	C19—C14—C15—C16	0.4 (4)
C6—O1—C5—O2	−2.1 (4)	C4—C14—C15—C16	178.0 (2)
C6—O1—C5—C1	179.4 (2)	C14—C15—C16—C17	0.1 (4)
N1—C1—C5—O2	−15.9 (4)	C15—C16—C17—C18	0.2 (4)
C2—C1—C5—O2	168.4 (3)	C15—C16—C17—C20	−179.9 (3)
N1—C1—C5—O1	162.7 (2)	C16—C17—C18—C19	−1.1 (4)
C2—C1—C5—O1	−13.1 (4)	C20—C17—C18—C19	179.0 (3)
C1—C2—C7—C12	134.7 (3)	C17—C18—C19—C14	1.6 (4)
C3—C2—C7—C12	−47.8 (4)	C15—C14—C19—C18	−1.3 (4)
C1—C2—C7—C8	−46.4 (4)	C4—C14—C19—C18	−178.9 (2)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1···O2^i	0.88	2.06	2.932 (3)	169

Symmetry code: (i) −x, −y+2, −z+1.