(E)-2-{[(2-Amino­phen­yl)imino]­meth­yl}-5-(benz­yl­oxy)phenol and (Z)-3-benz­yl­oxy-6-{[(5-chloro-2-hy­droxy­phen­yl)amino]­methyl­idene}cyclo­hexa-2,4-dien-1-one

The synthesis and structures of (E)-2-{[(2-amino­phen­yl)imino]­meth­yl}-5-(benz­yloxy)phenol (I) and (Z)-3-benz­yloxy-6-{[(5-chloro-2-hy­droxy­phen­yl)amino]­methyl­idene}cyclo­hexa-2,4-dien-1-one (II) are reported. The crystal structures of the mol­ecules are stabilized by N—H...O, O—H...O and C—H...π contacts. DFT calculations on the structure of (II) support the Keto–imine tautomeric form found in the solid state structure. The anti­oxident properties of both mol­ecules are investigated.

Key indicators

Structure: I

• Single-crystal X-ray study
• T = 293 K
• Mean [sigma](C-C) = 0.003 Å
• R factor = 0.049
• wR factor = 0.134
• Data-to-parameter ratio = 17.2

Structure: II

• Single-crystal X-ray study
• T = 293 K
• Mean [sigma](C-C) = 0.003 Å
• R factor = 0.042
• wR factor = 0.133
• Data-to-parameter ratio = 12.8

checkCIF/PLATON results

No syntax errors found



Datablock: I


Alert level C
PLAT905_ALERT_3_C Negative K value in the Analysis of Variance ...     -3.554 Report
PLAT910_ALERT_3_C Missing # of FCF Reflection(s) Below Theta(Min).          8 Note
PLAT911_ALERT_3_C Missing FCF Refl Between Thmin & STh/L=    0.600         24 Report

Alert level G
PLAT007_ALERT_5_G Number of Unrefined Donor-H Atoms ..............          3 Report
PLAT019_ALERT_1_G _diffrn_measured_fraction_theta_full/*_max < 1.0      0.997 Report
PLAT199_ALERT_1_G Reported _cell_measurement_temperature ..... (K)        293 Check
PLAT200_ALERT_1_G Reported   _diffrn_ambient_temperature ..... (K)        293 Check
PLAT432_ALERT_2_G Short Inter X...Y Contact  C13      ..C13              3.19 Ang.
PLAT933_ALERT_2_G Number of OMIT Records in Embedded .res File ...          9 Note
PLAT955_ALERT_1_G Reported (CIF) and Actual (FCF) Lmax Differ by .          1 Units
PLAT978_ALERT_2_G Number C-C Bonds with Positive Residual Density.          1 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

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




Datablock: II


Alert level B
PLAT230_ALERT_2_B Hirshfeld Test Diff for   C17      --C18       .        8.0 s.u.

Alert level C
PLAT480_ALERT_4_C Long H...A H-Bond Reported H7       ..CL1              2.84 Ang.
PLAT911_ALERT_3_C Missing FCF Refl Between Thmin & STh/L=    0.600         46 Report

Alert level G
PLAT154_ALERT_1_G The s.u.'s on the Cell Angles are Equal ..(Note)      0.002 Degree
PLAT199_ALERT_1_G Reported _cell_measurement_temperature ..... (K)        293 Check
PLAT200_ALERT_1_G Reported   _diffrn_ambient_temperature ..... (K)        293 Check
PLAT910_ALERT_3_G Missing # of FCF Reflection(s) Below Theta(Min).          2 Note
PLAT933_ALERT_2_G Number of OMIT Records in Embedded .res File ...         14 Note
PLAT978_ALERT_2_G Number C-C Bonds with Positive Residual Density.          6 Info

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

   3 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
   3 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
   1 ALERT type 4 Improvement, methodology, query or suggestion
   0 ALERT type 5 Informative message, check

---

Computing details

For both structures, data collection: APEX2 (Bruker, 2012); cell refinement: SAINT (Bruker, 2012); data reduction: SAINT (Bruker, 2012); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL2017 (Sheldrick, 2015); molecular graphics: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXTL (Sheldrick, 2008).

(E)-2-{[(2-Aminophenyl)imino]methyl}-5-(benzyloxy)phenol (I)

Crystal data

C20H18N2O2	F(000) = 1344
Mr = 318.36	Dx = 1.268 Mg m^−3
Monoclinic, C2/c	Mo Kα radiation, λ = 0.71073 Å
a = 35.1343 (12) Å	Cell parameters from 1907 reflections
b = 7.2564 (2) Å	θ = 2.9–21.9°
c = 13.1450 (5) Å	µ = 0.08 mm^−1
β = 95.553 (2)°	T = 293 K
V = 3335.57 (19) Å^3	Block, yellow
Z = 8	0.03 × 0.02 × 0.01 mm

Data collection

Bruker APEXII CCD diffractometer	Rint = 0.072
Detector resolution: 18.4 pixels mm^-1	θmax = 27.5°, θmin = 3.4°
φ and ω scans	h = −45→45
18218 measured reflections	k = −9→9
3811 independent reflections	l = −16→17
1915 reflections with I > 2σ(I)

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)] = 0.049	Hydrogen site location: mixed
wR(F^2) = 0.134	H atoms treated by a mixture of independent and constrained refinement
S = 1.00	w = 1/[σ^2(Fo^2) + (0.0527P)^2 + 0.5669P] where P = (Fo^2 + 2Fc^2)/3
3811 reflections	(Δ/σ)max = 0.001
221 parameters	Δρmax = 0.17 e Å^−3
0 restraints	Δρmin = −0.15 e Å^−3

Special details

Geometry. Bond distances, angles etc. have been calculated using the rounded fractional coordinates. All su's are estimated from the variances of the (full) variance-covariance matrix. The cell esds are taken into account in the estimation of distances, angles and torsion angles

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

	x	y	z	Uiso*/Ueq
O1	0.00836 (4)	−0.03108 (16)	0.12180 (11)	0.0578 (5)
O2	0.10314 (4)	0.43746 (16)	0.17382 (10)	0.0513 (5)
N1	−0.06331 (5)	0.0754 (2)	0.08936 (12)	0.0477 (6)
N2	−0.09669 (6)	−0.1879 (3)	0.19901 (17)	0.0913 (9)
C1	−0.10273 (6)	0.0392 (2)	0.06599 (15)	0.0458 (7)
C2	−0.12530 (6)	0.1274 (3)	−0.01145 (17)	0.0529 (8)
C3	−0.16347 (7)	0.0816 (3)	−0.03355 (19)	0.0653 (9)
C4	−0.17934 (7)	−0.0518 (3)	0.0237 (2)	0.0708 (10)
C5	−0.15720 (7)	−0.1400 (3)	0.1008 (2)	0.0683 (10)
C6	−0.11880 (6)	−0.1003 (3)	0.12233 (17)	0.0553 (8)
C7	−0.05090 (6)	0.2425 (3)	0.09311 (14)	0.0436 (7)
C8	−0.01110 (5)	0.2870 (2)	0.11319 (14)	0.0396 (6)
C9	0.01726 (6)	0.1499 (2)	0.12587 (14)	0.0411 (7)
C10	0.05547 (6)	0.1960 (2)	0.14368 (15)	0.0452 (7)
C11	0.06603 (5)	0.3795 (2)	0.15199 (14)	0.0410 (6)
C12	0.03863 (6)	0.5185 (2)	0.13959 (14)	0.0431 (7)
C13	0.00105 (6)	0.4708 (2)	0.12065 (14)	0.0421 (7)
C14	0.13205 (6)	0.2969 (3)	0.18376 (19)	0.0617 (9)
C15	0.16990 (6)	0.3854 (2)	0.21507 (18)	0.0490 (7)
C16	0.18486 (7)	0.3842 (3)	0.3151 (2)	0.0623 (9)
C17	0.22001 (7)	0.4634 (3)	0.3441 (2)	0.0693 (10)
C18	0.24053 (7)	0.5423 (3)	0.2725 (2)	0.0698 (10)
C19	0.22599 (7)	0.5434 (3)	0.1723 (2)	0.0715 (10)
C20	0.19090 (6)	0.4654 (3)	0.14359 (19)	0.0617 (9)
H1	−0.01490	−0.04310	0.11149	0.0870*
H2	−0.11464	0.21904	−0.04924	0.0640*
H2A	−0.10663	−0.27019	0.23540	0.1100*
H2B	−0.07285	−0.16065	0.21082	0.1100*
H3	−0.17822	0.14023	−0.08652	0.0780*
H4	−0.20504	−0.08226	0.01022	0.0850*
H5	−0.16836	−0.22861	0.13952	0.0820*
H7	−0.0691 (5)	0.349 (3)	0.0810 (13)	0.045 (5)*
H10	0.07401	0.10419	0.15006	0.0540*
H12	0.04583	0.64178	0.14416	0.0520*
H13	−0.01720	0.56385	0.11238	0.0510*
H14A	0.12613	0.20744	0.23476	0.0740*
H14B	0.13296	0.23331	0.11913	0.0740*
H16	0.17121	0.32937	0.36425	0.0750*
H17	0.22971	0.46292	0.41244	0.0830*
H18	0.26425	0.59506	0.29182	0.0840*
H19	0.23986	0.59698	0.12325	0.0860*
H20	0.18125	0.46665	0.07518	0.0740*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
O1	0.0526 (9)	0.0348 (7)	0.0852 (11)	−0.0032 (6)	0.0022 (8)	0.0001 (6)
O2	0.0397 (9)	0.0389 (7)	0.0745 (10)	0.0008 (6)	0.0021 (7)	−0.0048 (6)
N1	0.0457 (11)	0.0460 (10)	0.0507 (11)	−0.0054 (7)	0.0018 (8)	0.0016 (7)
N2	0.0912 (17)	0.0807 (15)	0.0962 (17)	−0.0325 (12)	−0.0211 (13)	0.0422 (12)
C1	0.0440 (13)	0.0420 (11)	0.0509 (13)	−0.0023 (9)	0.0028 (10)	−0.0036 (9)
C2	0.0527 (15)	0.0473 (11)	0.0581 (14)	0.0000 (9)	0.0020 (11)	0.0007 (10)
C3	0.0532 (16)	0.0590 (14)	0.0801 (18)	0.0082 (11)	−0.0113 (13)	−0.0071 (12)
C4	0.0454 (15)	0.0639 (15)	0.102 (2)	−0.0072 (11)	0.0012 (14)	−0.0144 (14)
C5	0.0598 (17)	0.0602 (14)	0.0848 (19)	−0.0201 (11)	0.0058 (14)	0.0032 (12)
C6	0.0544 (15)	0.0470 (12)	0.0633 (15)	−0.0100 (10)	−0.0002 (12)	0.0042 (10)
C7	0.0474 (13)	0.0430 (11)	0.0403 (12)	0.0003 (9)	0.0041 (9)	0.0017 (8)
C8	0.0417 (12)	0.0403 (10)	0.0365 (11)	−0.0009 (8)	0.0027 (9)	0.0003 (8)
C9	0.0476 (13)	0.0347 (10)	0.0411 (12)	−0.0006 (8)	0.0056 (10)	−0.0004 (8)
C10	0.0434 (13)	0.0369 (10)	0.0553 (13)	0.0036 (8)	0.0043 (10)	−0.0015 (9)
C11	0.0401 (12)	0.0418 (10)	0.0415 (11)	−0.0024 (8)	0.0056 (9)	−0.0018 (8)
C12	0.0471 (13)	0.0344 (10)	0.0472 (12)	−0.0014 (8)	0.0021 (10)	−0.0014 (8)
C13	0.0457 (13)	0.0380 (10)	0.0422 (12)	0.0044 (8)	0.0021 (9)	0.0006 (8)
C14	0.0454 (14)	0.0441 (12)	0.0954 (19)	0.0041 (9)	0.0055 (12)	−0.0047 (11)
C15	0.0398 (13)	0.0381 (10)	0.0683 (15)	0.0037 (8)	0.0017 (11)	0.0001 (9)
C16	0.0557 (16)	0.0601 (14)	0.0720 (18)	0.0053 (11)	0.0111 (13)	0.0067 (11)
C17	0.0664 (18)	0.0707 (15)	0.0673 (17)	0.0101 (13)	−0.0113 (14)	−0.0064 (12)
C18	0.0473 (15)	0.0571 (14)	0.102 (2)	−0.0037 (11)	−0.0074 (15)	−0.0060 (13)
C19	0.0623 (17)	0.0643 (15)	0.088 (2)	−0.0158 (12)	0.0079 (15)	0.0094 (13)
C20	0.0618 (16)	0.0554 (13)	0.0668 (16)	−0.0088 (11)	0.0014 (13)	0.0057 (11)

Geometric parameters (Å, º)

O1—C9	1.3498 (19)	C14—C15	1.498 (3)
O2—C11	1.374 (2)	C15—C20	1.378 (3)
O2—C14	1.437 (3)	C15—C16	1.368 (3)
N1—C1	1.414 (3)	C16—C17	1.382 (3)
N1—C7	1.288 (3)	C17—C18	1.366 (4)
O1—H1	0.8200	C18—C19	1.366 (4)
N2—C6	1.368 (3)	C19—C20	1.376 (3)
C1—C2	1.385 (3)	C2—H2	0.9300
C1—C6	1.405 (3)	C3—H3	0.9300
N2—H2A	0.8600	C4—H4	0.9300
N2—H2B	0.8600	C5—H5	0.9300
C2—C3	1.385 (3)	C7—H7	1.01 (2)
C3—C4	1.377 (3)	C10—H10	0.9300
C4—C5	1.375 (4)	C12—H12	0.9300
C5—C6	1.382 (3)	C13—H13	0.9300
C7—C8	1.435 (3)	C14—H14A	0.9700
C8—C9	1.407 (2)	C14—H14B	0.9700
C8—C13	1.401 (2)	C16—H16	0.9300
C9—C10	1.381 (3)	C17—H17	0.9300
C10—C11	1.384 (2)	C18—H18	0.9300
C11—C12	1.393 (2)	C19—H19	0.9300
C12—C13	1.364 (3)	C20—H20	0.9300
C11—O2—C14	116.75 (13)	C17—C18—C19	119.6 (2)
C1—N1—C7	120.27 (16)	C18—C19—C20	120.3 (2)
C9—O1—H1	109.00	C15—C20—C19	120.7 (2)
N1—C1—C2	123.57 (17)	C1—C2—H2	119.00
C2—C1—C6	119.33 (19)	C3—C2—H2	119.00
N1—C1—C6	117.04 (17)	C2—C3—H3	120.00
H2A—N2—H2B	120.00	C4—C3—H3	120.00
C6—N2—H2B	120.00	C3—C4—H4	120.00
C1—C2—C3	121.1 (2)	C5—C4—H4	120.00
C6—N2—H2A	120.00	C4—C5—H5	119.00
C2—C3—C4	119.3 (2)	C6—C5—H5	119.00
C3—C4—C5	120.0 (2)	N1—C7—H7	120.6 (11)
C4—C5—C6	121.7 (2)	C8—C7—H7	116.7 (11)
N2—C6—C5	121.8 (2)	C9—C10—H10	120.00
C1—C6—C5	118.5 (2)	C11—C10—H10	120.00
N2—C6—C1	119.7 (2)	C11—C12—H12	121.00
N1—C7—C8	122.64 (19)	C13—C12—H12	121.00
C7—C8—C9	121.96 (15)	C8—C13—H13	119.00
C7—C8—C13	120.81 (17)	C12—C13—H13	119.00
C9—C8—C13	117.23 (17)	O2—C14—H14A	110.00
O1—C9—C10	117.38 (16)	O2—C14—H14B	110.00
C8—C9—C10	120.97 (14)	C15—C14—H14A	110.00
O1—C9—C8	121.65 (17)	C15—C14—H14B	110.00
C9—C10—C11	119.68 (16)	H14A—C14—H14B	108.00
C10—C11—C12	120.70 (17)	C15—C16—H16	120.00
O2—C11—C10	123.57 (15)	C17—C16—H16	120.00
O2—C11—C12	115.72 (14)	C16—C17—H17	120.00
C11—C12—C13	118.90 (14)	C18—C17—H17	120.00
C8—C13—C12	122.50 (16)	C17—C18—H18	120.00
O2—C14—C15	108.77 (16)	C19—C18—H18	120.00
C14—C15—C16	120.6 (2)	C18—C19—H19	120.00
C14—C15—C20	120.9 (2)	C20—C19—H19	120.00
C16—C15—C20	118.5 (2)	C15—C20—H20	120.00
C15—C16—C17	120.8 (2)	C19—C20—H20	120.00
C16—C17—C18	120.1 (2)
C14—O2—C11—C10	2.8 (3)	C13—C8—C9—O1	178.84 (17)
C14—O2—C11—C12	−178.09 (17)	C13—C8—C9—C10	−0.8 (3)
C11—O2—C14—C15	−175.82 (17)	C7—C8—C13—C12	−179.96 (18)
C7—N1—C1—C2	44.0 (3)	C9—C8—C13—C12	−0.1 (3)
C7—N1—C1—C6	−139.06 (19)	O1—C9—C10—C11	−177.83 (17)
C1—N1—C7—C8	−177.94 (17)	C8—C9—C10—C11	1.8 (3)
N1—C1—C2—C3	177.54 (19)	C9—C10—C11—O2	177.20 (17)
C6—C1—C2—C3	0.6 (3)	C9—C10—C11—C12	−1.9 (3)
N1—C1—C6—N2	3.0 (3)	O2—C11—C12—C13	−178.16 (16)
N1—C1—C6—C5	−179.52 (19)	C10—C11—C12—C13	1.0 (3)
C2—C1—C6—N2	−179.9 (2)	C11—C12—C13—C8	0.0 (3)
C2—C1—C6—C5	−2.4 (3)	O2—C14—C15—C16	99.2 (2)
C1—C2—C3—C4	1.1 (3)	O2—C14—C15—C20	−82.5 (2)
C2—C3—C4—C5	−1.0 (4)	C14—C15—C16—C17	179.1 (2)
C3—C4—C5—C6	−0.8 (4)	C20—C15—C16—C17	0.8 (3)
C4—C5—C6—N2	−180.0 (2)	C14—C15—C20—C19	−178.73 (19)
C4—C5—C6—C1	2.5 (3)	C16—C15—C20—C19	−0.4 (3)
N1—C7—C8—C9	2.8 (3)	C15—C16—C17—C18	−0.8 (3)
N1—C7—C8—C13	−177.43 (18)	C16—C17—C18—C19	0.4 (3)
C7—C8—C9—O1	−1.4 (3)	C17—C18—C19—C20	−0.1 (3)
C7—C8—C9—C10	179.05 (18)	C18—C19—C20—C15	0.1 (3)

Hydrogen-bond geometry (Å, º)

Cg1 and Cg3 are the centroids of the C1–C6 and C15–C20 rings respectively.

D—H···A	D—H	H···A	D···A	D—H···A
O1—H1···N1	0.82	1.90	2.629 (2)	147
N2—H2A···O2^i	0.86	2.43	3.211 (3)	151
C14—H14B···Cg1^ii	0.97	2.74	3.704 (3)	171
C16—H16···Cg1^iii	0.93	2.96	3.792 (3)	150
C18—H18···Cg3^iv	0.93	2.94	3.620 (2)	131

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

(Z)-3-Benzyloxy-6-{[(5-chloro-2-hydroxyphenyl)amino]methylidene}cyclohexa-2,4-dien-1-one (II)

Crystal data

C20H16ClNO3	Z = 2
Mr = 353.79	F(000) = 368
Triclinic, P1	Dx = 1.412 Mg m^−3
a = 5.9590 (2) Å	Mo Kα radiation, λ = 0.71073 Å
b = 7.8710 (3) Å	Cell parameters from 5281 reflections
c = 17.9743 (6) Å	θ = 2.7–30.7°
α = 98.381 (2)°	µ = 0.25 mm^−1
β = 93.817 (2)°	T = 293 K
γ = 90.294 (2)°	Block, orange
V = 832.11 (5) Å^3	0.03 × 0.02 × 0.01 mm

Data collection

Bruker APEXII CCD diffractometer	Rint = 0.025
Detector resolution: 18.4 pixels mm^-1	θmax = 25.5°, θmin = 2.6°
φ and ω scans	h = −6→7
13513 measured reflections	k = −9→9
3052 independent reflections	l = −21→21
2490 reflections with I > 2σ(I)

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)] = 0.042	Hydrogen site location: mixed
wR(F^2) = 0.133	H atoms treated by a mixture of independent and constrained refinement
S = 1.10	w = 1/[σ^2(Fo^2) + (0.0727P)^2 + 0.2078P] where P = (Fo^2 + 2Fc^2)/3
3052 reflections	(Δ/σ)max < 0.001
238 parameters	Δρmax = 0.21 e Å^−3
0 restraints	Δρmin = −0.21 e Å^−3

Special details

Geometry. Bond distances, angles etc. have been calculated using the rounded fractional coordinates. All su's are estimated from the variances of the (full) variance-covariance matrix. The cell esds are taken into account in the estimation of distances, angles and torsion angles

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

	x	y	z	Uiso*/Ueq
Cl1	0.93492 (8)	0.93423 (7)	−0.13197 (3)	0.0533 (2)
O1	0.1309 (2)	0.6289 (2)	0.14736 (7)	0.0518 (5)
O2	0.1581 (3)	0.5583 (2)	−0.05318 (9)	0.0546 (5)
O3	0.3158 (2)	0.7742 (2)	0.41212 (7)	0.0520 (5)
N1	0.4214 (3)	0.7241 (2)	0.05641 (8)	0.0382 (5)
C1	0.4780 (3)	0.7305 (2)	−0.01782 (10)	0.0348 (5)
C2	0.3343 (3)	0.6417 (2)	−0.07572 (10)	0.0381 (6)
C3	0.3805 (3)	0.6429 (3)	−0.15011 (10)	0.0444 (6)
C4	0.5643 (3)	0.7329 (3)	−0.16776 (10)	0.0433 (6)
C5	0.7028 (3)	0.8202 (2)	−0.11011 (10)	0.0374 (6)
C6	0.6635 (3)	0.8205 (2)	−0.03551 (10)	0.0371 (5)
C7	0.5388 (3)	0.7860 (2)	0.11873 (10)	0.0394 (6)
C8	0.4718 (3)	0.7766 (2)	0.19092 (10)	0.0380 (5)
C9	0.2627 (3)	0.6945 (2)	0.20317 (10)	0.0380 (5)
C10	0.2119 (3)	0.6906 (3)	0.27886 (10)	0.0426 (6)
C11	0.3535 (3)	0.7669 (3)	0.33778 (10)	0.0409 (6)
C12	0.5562 (3)	0.8502 (3)	0.32557 (11)	0.0481 (7)
C13	0.6123 (3)	0.8526 (3)	0.25418 (11)	0.0465 (6)
C14	0.1117 (4)	0.6974 (3)	0.43003 (11)	0.0572 (8)
C15	0.1044 (4)	0.7217 (3)	0.51439 (10)	0.0474 (7)
C16	−0.0740 (4)	0.8010 (3)	0.54911 (14)	0.0632 (8)
C17	−0.0843 (5)	0.8143 (3)	0.62686 (15)	0.0719 (9)
C18	0.0817 (5)	0.7470 (3)	0.66975 (12)	0.0631 (8)
C19	0.2599 (5)	0.6690 (4)	0.63599 (13)	0.0677 (9)
C20	0.2723 (4)	0.6576 (3)	0.55862 (12)	0.0621 (8)
H1	0.299 (4)	0.674 (3)	0.0639 (13)	0.057 (7)*
H2	0.080 (5)	0.509 (4)	−0.0877 (18)	0.086 (10)*
H3	0.28678	0.58262	−0.18855	0.0530*
H4	0.59415	0.73465	−0.21778	0.0520*
H6	0.75959	0.88004	0.00245	0.0450*
H7	0.686 (4)	0.840 (3)	0.1147 (11)	0.043 (5)*
H10	0.08097	0.63559	0.28872	0.0510*
H12	0.64933	0.90248	0.36612	0.0580*
H13	0.74667	0.90542	0.24615	0.0560*
H14A	0.10695	0.57595	0.41018	0.0690*
H14B	−0.01698	0.75127	0.40768	0.0690*
H16	−0.18852	0.84600	0.52046	0.0760*
H17	−0.20480	0.86928	0.64988	0.0860*
H18	0.07282	0.75461	0.72159	0.0760*
H19	0.37329	0.62325	0.66483	0.0810*
H20	0.39585	0.60591	0.53619	0.0740*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
Cl1	0.0448 (3)	0.0693 (4)	0.0476 (3)	−0.0148 (2)	0.0136 (2)	0.0105 (2)
O1	0.0473 (8)	0.0697 (10)	0.0352 (7)	−0.0287 (7)	−0.0005 (6)	−0.0002 (6)
O2	0.0469 (8)	0.0723 (11)	0.0437 (8)	−0.0303 (8)	−0.0049 (7)	0.0105 (7)
O3	0.0513 (8)	0.0735 (10)	0.0313 (7)	−0.0160 (7)	0.0047 (6)	0.0075 (6)
N1	0.0356 (8)	0.0456 (9)	0.0330 (8)	−0.0118 (7)	0.0042 (6)	0.0039 (6)
C1	0.0346 (9)	0.0376 (9)	0.0323 (9)	−0.0039 (7)	0.0041 (7)	0.0046 (7)
C2	0.0340 (9)	0.0399 (10)	0.0397 (10)	−0.0075 (8)	−0.0029 (8)	0.0066 (7)
C3	0.0469 (11)	0.0494 (11)	0.0349 (10)	−0.0082 (9)	−0.0067 (8)	0.0037 (8)
C4	0.0487 (11)	0.0505 (11)	0.0310 (9)	−0.0036 (9)	0.0038 (8)	0.0068 (8)
C5	0.0340 (9)	0.0404 (10)	0.0385 (10)	−0.0029 (8)	0.0062 (7)	0.0066 (7)
C6	0.0343 (9)	0.0421 (10)	0.0335 (9)	−0.0077 (8)	0.0011 (7)	0.0017 (7)
C7	0.0352 (10)	0.0454 (11)	0.0373 (10)	−0.0108 (8)	0.0025 (8)	0.0052 (8)
C8	0.0353 (9)	0.0440 (10)	0.0345 (9)	−0.0087 (8)	0.0025 (7)	0.0051 (7)
C9	0.0370 (9)	0.0407 (10)	0.0352 (9)	−0.0089 (8)	0.0021 (7)	0.0028 (7)
C10	0.0388 (10)	0.0513 (11)	0.0379 (10)	−0.0134 (8)	0.0057 (8)	0.0063 (8)
C11	0.0426 (10)	0.0484 (11)	0.0321 (9)	−0.0043 (8)	0.0034 (8)	0.0068 (8)
C12	0.0414 (11)	0.0641 (13)	0.0370 (10)	−0.0152 (9)	−0.0041 (8)	0.0047 (9)
C13	0.0376 (10)	0.0631 (13)	0.0380 (10)	−0.0178 (9)	0.0004 (8)	0.0066 (9)
C14	0.0551 (13)	0.0804 (16)	0.0358 (10)	−0.0195 (11)	0.0051 (9)	0.0072 (10)
C15	0.0520 (12)	0.0559 (12)	0.0340 (10)	−0.0134 (9)	0.0084 (9)	0.0035 (8)
C16	0.0670 (15)	0.0686 (15)	0.0584 (14)	0.0097 (12)	0.0141 (12)	0.0195 (11)
C17	0.0911 (19)	0.0635 (15)	0.0647 (15)	0.0071 (14)	0.0405 (15)	0.0050 (12)
C18	0.0877 (18)	0.0656 (15)	0.0342 (10)	−0.0144 (13)	0.0125 (11)	−0.0020 (10)
C19	0.0683 (16)	0.0918 (19)	0.0397 (12)	−0.0086 (14)	−0.0080 (11)	0.0046 (11)
C20	0.0496 (13)	0.0896 (18)	0.0434 (12)	0.0007 (12)	0.0051 (10)	−0.0033 (11)

Geometric parameters (Å, º)

Cl1—C5	1.7423 (18)	C14—C15	1.504 (3)
O1—C9	1.277 (2)	C15—C20	1.380 (3)
O2—C2	1.351 (2)	C15—C16	1.375 (3)
O3—C11	1.363 (2)	C16—C17	1.392 (4)
O3—C14	1.432 (3)	C17—C18	1.370 (4)
N1—C1	1.406 (2)	C18—C19	1.363 (4)
N1—C7	1.309 (2)	C19—C20	1.387 (3)
O2—H2	0.80 (3)	C3—H3	0.9300
C1—C2	1.403 (2)	C4—H4	0.9300
C1—C6	1.389 (2)	C6—H6	0.9300
N1—H1	0.86 (2)	C7—H7	0.98 (2)
C2—C3	1.384 (3)	C10—H10	0.9300
C3—C4	1.381 (3)	C12—H12	0.9300
C4—C5	1.378 (3)	C13—H13	0.9300
C5—C6	1.376 (3)	C14—H14A	0.9700
C7—C8	1.395 (3)	C14—H14B	0.9700
C8—C13	1.422 (3)	C16—H16	0.9300
C8—C9	1.445 (2)	C17—H17	0.9300
C9—C10	1.418 (3)	C18—H18	0.9300
C10—C11	1.373 (3)	C19—H19	0.9300
C11—C12	1.416 (3)	C20—H20	0.9300
C12—C13	1.350 (3)
C11—O3—C14	117.35 (14)	C15—C16—C17	120.4 (2)
C1—N1—C7	127.15 (17)	C16—C17—C18	120.5 (2)
C2—O2—H2	113 (2)	C17—C18—C19	119.6 (2)
N1—C1—C6	123.47 (16)	C18—C19—C20	120.1 (2)
C2—C1—C6	119.86 (16)	C15—C20—C19	121.1 (2)
N1—C1—C2	116.67 (16)	C2—C3—H3	120.00
C1—N1—H1	119.4 (15)	C4—C3—H3	120.00
C7—N1—H1	113.4 (15)	C3—C4—H4	121.00
C1—C2—C3	119.57 (16)	C5—C4—H4	121.00
O2—C2—C3	124.73 (17)	C1—C6—H6	121.00
O2—C2—C1	115.70 (16)	C5—C6—H6	121.00
C2—C3—C4	120.61 (17)	N1—C7—H7	118.2 (12)
C3—C4—C5	118.97 (17)	C8—C7—H7	117.5 (12)
Cl1—C5—C4	119.22 (14)	C9—C10—H10	120.00
Cl1—C5—C6	118.73 (13)	C11—C10—H10	120.00
C4—C5—C6	122.05 (17)	C11—C12—H12	121.00
C1—C6—C5	118.93 (16)	C13—C12—H12	120.00
N1—C7—C8	124.28 (17)	C8—C13—H13	119.00
C9—C8—C13	119.22 (16)	C12—C13—H13	119.00
C7—C8—C9	121.97 (16)	O3—C14—H14A	110.00
C7—C8—C13	118.80 (16)	O3—C14—H14B	110.00
O1—C9—C8	120.48 (16)	C15—C14—H14A	110.00
O1—C9—C10	122.15 (16)	C15—C14—H14B	110.00
C8—C9—C10	117.36 (16)	H14A—C14—H14B	108.00
C9—C10—C11	120.87 (17)	C15—C16—H16	120.00
C10—C11—C12	121.61 (17)	C17—C16—H16	120.00
O3—C11—C12	113.29 (16)	C16—C17—H17	120.00
O3—C11—C10	125.09 (17)	C18—C17—H17	120.00
C11—C12—C13	119.03 (18)	C17—C18—H18	120.00
C8—C13—C12	121.89 (18)	C19—C18—H18	120.00
O3—C14—C15	108.26 (17)	C18—C19—H19	120.00
C14—C15—C16	121.1 (2)	C20—C19—H19	120.00
C14—C15—C20	120.6 (2)	C15—C20—H20	119.00
C16—C15—C20	118.32 (19)	C19—C20—H20	119.00
C14—O3—C11—C10	−0.5 (3)	C7—C8—C9—C10	179.38 (17)
C14—O3—C11—C12	178.36 (19)	C13—C8—C9—O1	178.32 (17)
C11—O3—C14—C15	−179.52 (18)	C13—C8—C9—C10	−1.6 (3)
C7—N1—C1—C2	174.54 (17)	C7—C8—C13—C12	179.1 (2)
C7—N1—C1—C6	−6.3 (3)	C9—C8—C13—C12	0.1 (3)
C1—N1—C7—C8	179.41 (17)	O1—C9—C10—C11	−177.95 (19)
N1—C1—C2—O2	−0.6 (2)	C8—C9—C10—C11	2.0 (3)
N1—C1—C2—C3	180.00 (18)	C9—C10—C11—O3	177.97 (19)
C6—C1—C2—O2	−179.83 (16)	C9—C10—C11—C12	−0.8 (3)
C6—C1—C2—C3	0.8 (3)	O3—C11—C12—C13	−179.7 (2)
N1—C1—C6—C5	−179.28 (16)	C10—C11—C12—C13	−0.8 (3)
C2—C1—C6—C5	−0.2 (2)	C11—C12—C13—C8	1.2 (3)
O2—C2—C3—C4	179.61 (19)	O3—C14—C15—C16	124.1 (2)
C1—C2—C3—C4	−1.1 (3)	O3—C14—C15—C20	−58.9 (3)
C2—C3—C4—C5	0.7 (3)	C14—C15—C16—C17	176.5 (2)
C3—C4—C5—Cl1	−179.94 (17)	C20—C15—C16—C17	−0.5 (4)
C3—C4—C5—C6	0.0 (3)	C14—C15—C20—C19	−175.6 (2)
Cl1—C5—C6—C1	179.67 (13)	C16—C15—C20—C19	1.4 (4)
C4—C5—C6—C1	−0.2 (3)	C15—C16—C17—C18	−0.7 (4)
N1—C7—C8—C9	0.5 (3)	C16—C17—C18—C19	1.1 (4)
N1—C7—C8—C13	−178.51 (18)	C17—C18—C19—C20	−0.2 (4)
C7—C8—C9—O1	−0.7 (3)	C18—C19—C20—C15	−1.1 (4)

Hydrogen-bond geometry (Å, º)

Cg3 is the centroid of the C15–C20 ring.

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1···O1	0.86 (2)	1.93 (2)	2.637 (2)	139 (2)
N1—H1···O2	0.86 (2)	2.27 (2)	2.620 (2)	104.5 (18)
O2—H2···O1^i	0.80 (3)	1.84 (3)	2.619 (2)	165 (3)
C7—H7···Cl1^ii	0.98 (2)	2.84 (2)	3.7971 (18)	164.5 (17)
C14—H14A···Cg3^iii	0.97	2.71	3.569 (3)	148

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