2-Hydr­oxy-6-[(2-hydroxy­phenyl­amino)methyl­ene]cyclo­hexa­-2,4-dienone

Koşar, B.; Albayrak, C.; Odabaşoğlu, M.; Büyükgüngör, O.

doi:10.1107/S160053680500807X

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2-Hydroxy-6-[(2-hydroxyphenylamino)methylene]cyclohexa-2,4-dienone

B. Koşar, C. Albayrak, M. Odabaşoğlu and O. Büyükgüngör

The title compound, C₁₃H₁₁NO₃, adopts the keto–amine tautomeric form, with the H atom located on N rather than on O. This H atom is involved in a strong intramolecular hydrogen bond. There are two independent molecules in the asymmetric unit. The molecules are linked by intramolecular N—H

O and O—H

O and intermolecular O—H

O hydrogen bonds into a three-dimensional network.

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Supporting information

	Crystallographic Information File (CIF) https://doi.org/10.1107/S160053680500807X/bt6617sup1.cif Contains datablocks global, I
	Structure factor file (CIF format) https://doi.org/10.1107/S160053680500807X/bt6617Isup2.hkl Contains datablock I

CCDC reference: 270238

checkCIF report

Key indicators

Single-crystal X-ray study
T = 293 K
Mean (C-C) = 0.008 Å
R factor = 0.098
wR factor = 0.296
Data-to-parameter ratio = 17.4

checkCIF/PLATON results

No syntax errors found



Alert level B
DIFMX01_ALERT_2_B  The maximum difference density is > 0.1*ZMAX*1.00
            _refine_diff_density_max given =      0.883
            Test value =      0.800
PLAT026_ALERT_3_B Ratio Observed / Unique Reflections too Low ....         33 Perc.
PLAT097_ALERT_2_B Maximum (Positive) Residual Density ............       0.88 e/A   3
PLAT415_ALERT_2_B Short Inter D-H..H-X       H5A    ..  H33B    ..       2.01 Ang.
PLAT415_ALERT_2_B Short Inter D-H..H-X       H5B    ..  H33A    ..       2.03 Ang.

Alert level C
DIFMX02_ALERT_1_C  The minimum difference density is > 0.1*ZMAX*0.75
            The relevant atom site should be identified.
RFACR01_ALERT_3_C  The value of the weighted R factor is > 0.25
            Weighted R factor given   0.296
RINTA01_ALERT_3_C  The value of Rint is greater than 0.10
            Rint given   0.113
PLAT020_ALERT_3_C The value of Rint is greater than 0.10 .........       0.11
PLAT084_ALERT_2_C High R2 Value ..................................       0.30
PLAT094_ALERT_2_C Ratio of Maximum / Minimum Residual Density ....       3.42
PLAT125_ALERT_4_C No _symmetry_space_group_name_Hall Given .......          ?
PLAT199_ALERT_1_C Check the Reported cell_measurement_temperature         293
PLAT200_ALERT_1_C Check the Reported cell_ambient_temperature ....        293
PLAT222_ALERT_3_C Large Non-Solvent    H     Ueq(max)/Ueq(min) ...       3.09 Ratio
PLAT340_ALERT_3_C Low Bond Precision on C-C bonds (x 1000) Ang ...          8
PLAT417_ALERT_2_C Short Inter D-H..H-D       H1A1   ..  H33B    ..       2.14 Ang.
PLAT720_ALERT_4_C Number of Unusual/Non-Standard Label(s) ........          2

   0 ALERT level A = In general: serious problem
   5 ALERT level B = Potentially serious problem
  13 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
   7 ALERT type 2 Indicator that the structure model may be wrong or deficient
   6 ALERT type 3 Indicator that the structure quality may be low
   2 ALERT type 4 Improvement, methodology, query or suggestion

Computing details top

Data collection: X-AREA (Stoe & Cie, 2002); cell refinement: X-AREA; 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).

2-Hydroxy-6-[(2-hydroxyphenylamino)methylene]cyclohexa-2,4-dienone top

Crystal data top

C₁₃H₁₁NO₃	Z = 4
M_r = 229.23	F(000) = 480
Triclinic, P1	D_x = 1.433 Mg m⁻³
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 8.938 (2) Å	Cell parameters from 9705 reflections
b = 10.520 (3) Å	θ = 2.2–27.0°
c = 12.548 (3) Å	µ = 0.10 mm⁻¹
α = 67.726 (18)°	T = 293 K
β = 89.769 (18)°	Plate, red
γ = 77.689 (18)°	0.38 × 0.26 × 0.07 mm
V = 1062.9 (5) Å³

Data collection top

Stoe IPDS-2 diffractometer	5355 independent reflections
Radiation source: fine-focus sealed tube	1774 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.113
Detector resolution: 6.67 pixels mm^-1	θ_max = 28.5°, θ_min = 2.3°
rotation method scans	h = −10→11
Absorption correction: integration (X-RED32; Stoe & Cie, 2002)	k = −14→14
T_min = 0.965, T_max = 0.992	l = −16→16
18950 measured reflections

Refinement top

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)] = 0.098	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.296	H-atom parameters constrained
S = 0.89	w = 1/[σ²(F_o²) + (0.145P)²] where P = (F_o² + 2F_c²)/3
5355 reflections	(Δ/σ)_max < 0.001
307 parameters	Δρ_max = 0.88 e Å⁻³
0 restraints	Δρ_min = −0.26 e Å⁻³

Special details top

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 (Å²) top

	x	y	z	U_iso*/U_eq
C1A	0.5830 (5)	0.6433 (5)	0.4334 (4)	0.0360 (11)
N1A	0.7138 (5)	0.5296 (4)	0.4629 (4)	0.0404 (10)
H1A	0.7369	0.4943	0.4117	0.048*
C8A	0.9324 (6)	0.3592 (5)	0.5851 (4)	0.0384 (11)
O2A	0.9061 (4)	0.3443 (4)	0.4015 (3)	0.0553 (10)
C5A	0.3613 (6)	0.7853 (5)	0.3007 (4)	0.0435 (12)
H5A	0.2998	0.8063	0.2339	0.052*
O1A	0.5320 (5)	0.5886 (4)	0.2759 (4)	0.0637 (12)
H1A1	0.4701	0.6134	0.2198	0.096*
C6A	0.4908 (6)	0.6744 (5)	0.3339 (4)	0.0386 (11)
C13A	0.9737 (6)	0.2978 (6)	0.5041 (4)	0.0424 (12)
C7A	0.8026 (6)	0.4727 (5)	0.5581 (4)	0.0394 (11)
H7A	0.7786	0.5103	0.6139	0.047*
C9A	1.0153 (6)	0.3097 (6)	0.6935 (5)	0.0459 (13)
H9A	0.9861	0.3526	0.7452	0.055*
C4A	0.3245 (6)	0.8641 (6)	0.3676 (5)	0.0470 (13)
H4A	0.2385	0.9388	0.3453	0.056*
C12A	1.0976 (7)	0.1775 (6)	0.5411 (5)	0.0523 (14)
C11A	1.1794 (7)	0.1297 (6)	0.6451 (5)	0.0530 (14)
H11A	1.2620	0.0520	0.6655	0.064*
C10A	1.1397 (6)	0.1973 (6)	0.7220 (5)	0.0510 (14)
H10A	1.1978	0.1660	0.7922	0.061*
C2A	0.5438 (6)	0.7212 (6)	0.5010 (5)	0.0493 (13)
H2A	0.6035	0.6994	0.5688	0.059*
C3A	0.4141 (7)	0.8327 (6)	0.4668 (5)	0.0543 (15)
H3A	0.3883	0.8861	0.5114	0.065*
O3A	1.1429 (6)	0.1140 (6)	0.4661 (4)	0.0969 (19)
H33A	1.0846	0.1524	0.4069	0.145*
C1B	0.1555 (5)	0.3533 (5)	0.0654 (4)	0.0371 (11)
N1B	0.2288 (5)	0.4681 (4)	0.0356 (4)	0.0403 (10)
H1B	0.2341	0.5036	0.0865	0.048*
C8B	0.3615 (5)	0.6379 (5)	−0.0858 (4)	0.0355 (11)
C13B	0.3749 (6)	0.6992 (5)	−0.0049 (4)	0.0405 (12)
O2B	0.3301 (5)	0.6494 (4)	0.0982 (3)	0.0526 (10)
C12B	0.4387 (6)	0.8185 (6)	−0.0403 (4)	0.0460 (13)
C7B	0.2885 (5)	0.5245 (5)	−0.0604 (4)	0.0377 (11)
H7B	0.2829	0.4876	−0.1166	0.045*
C6B	0.0744 (5)	0.3247 (5)	0.1635 (4)	0.0396 (11)
C9B	0.4192 (6)	0.6909 (5)	−0.1947 (4)	0.0421 (12)
H9B	0.4115	0.6489	−0.2471	0.051*
C5B	0.0012 (6)	0.2123 (6)	0.1968 (5)	0.0481 (13)
H5B	−0.0510	0.1912	0.2634	0.058*
C11B	0.4945 (6)	0.8684 (5)	−0.1458 (4)	0.0452 (13)
H11B	0.5384	0.9461	−0.1662	0.054*
O1B	0.0710 (5)	0.4116 (4)	0.2198 (4)	0.0653 (12)
H1B1	0.0213	0.3872	0.2762	0.098*
C4B	0.0069 (7)	0.1330 (6)	0.1304 (5)	0.0527 (14)
H4B	−0.0419	0.0583	0.1523	0.063*
C10B	0.4861 (6)	0.8030 (5)	−0.2239 (5)	0.0452 (12)
H10B	0.5261	0.8362	−0.2952	0.054*
C2B	0.1591 (6)	0.2745 (6)	−0.0020 (5)	0.0490 (14)
H2B	0.2107	0.2952	−0.0688	0.059*
O3B	0.4511 (7)	0.8783 (5)	0.0362 (4)	0.0848 (16)
H33B	0.4290	0.8284	0.0995	0.127*
C3B	0.0841 (7)	0.1635 (6)	0.0320 (5)	0.0586 (16)
H3B	0.0865	0.1096	−0.0124	0.070*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
C1A	0.030 (2)	0.035 (3)	0.042 (3)	−0.006 (2)	0.006 (2)	−0.015 (2)
N1A	0.039 (2)	0.041 (2)	0.044 (2)	−0.0089 (19)	0.0090 (19)	−0.021 (2)
C8A	0.034 (3)	0.035 (3)	0.046 (3)	−0.007 (2)	0.009 (2)	−0.016 (2)
O2A	0.055 (2)	0.070 (3)	0.042 (2)	−0.005 (2)	0.0024 (18)	−0.0279 (19)
C5A	0.042 (3)	0.045 (3)	0.042 (3)	−0.005 (2)	0.000 (2)	−0.018 (2)
O1A	0.069 (3)	0.072 (3)	0.062 (3)	−0.001 (2)	−0.011 (2)	−0.046 (2)
C6A	0.037 (3)	0.038 (3)	0.048 (3)	−0.011 (2)	0.008 (2)	−0.023 (2)
C13A	0.036 (3)	0.049 (3)	0.039 (3)	−0.003 (2)	0.002 (2)	−0.017 (2)
C7A	0.039 (3)	0.043 (3)	0.036 (3)	−0.012 (2)	0.010 (2)	−0.014 (2)
C9A	0.044 (3)	0.049 (3)	0.047 (3)	−0.008 (3)	0.001 (2)	−0.022 (3)
C4A	0.037 (3)	0.047 (3)	0.054 (3)	0.000 (2)	0.005 (2)	−0.021 (3)
C12A	0.052 (3)	0.054 (3)	0.053 (3)	0.004 (3)	0.007 (3)	−0.031 (3)
C11A	0.047 (3)	0.049 (3)	0.056 (3)	−0.004 (3)	0.004 (3)	−0.016 (3)
C10A	0.041 (3)	0.056 (3)	0.050 (3)	−0.004 (3)	−0.008 (2)	−0.017 (3)
C2A	0.042 (3)	0.068 (4)	0.041 (3)	−0.002 (3)	0.003 (2)	−0.030 (3)
C3A	0.051 (3)	0.056 (3)	0.052 (3)	0.010 (3)	0.003 (3)	−0.029 (3)
O3A	0.106 (4)	0.100 (4)	0.080 (3)	0.034 (3)	−0.017 (3)	−0.060 (3)
C1B	0.036 (3)	0.038 (3)	0.041 (3)	−0.008 (2)	−0.002 (2)	−0.019 (2)
N1B	0.040 (2)	0.044 (2)	0.042 (2)	−0.008 (2)	−0.0049 (19)	−0.023 (2)
C8B	0.028 (2)	0.036 (2)	0.042 (3)	−0.003 (2)	−0.004 (2)	−0.017 (2)
C13B	0.039 (3)	0.050 (3)	0.035 (3)	−0.013 (2)	−0.001 (2)	−0.017 (2)
O2B	0.062 (3)	0.063 (2)	0.045 (2)	−0.023 (2)	0.0070 (18)	−0.0297 (19)
C12B	0.059 (3)	0.050 (3)	0.039 (3)	−0.020 (3)	0.000 (2)	−0.025 (2)
C7B	0.036 (3)	0.038 (3)	0.041 (3)	−0.007 (2)	−0.002 (2)	−0.018 (2)
C6B	0.030 (3)	0.043 (3)	0.048 (3)	−0.001 (2)	0.003 (2)	−0.025 (2)
C9B	0.047 (3)	0.042 (3)	0.042 (3)	−0.007 (2)	0.003 (2)	−0.023 (2)
C5B	0.045 (3)	0.052 (3)	0.048 (3)	−0.019 (3)	0.006 (2)	−0.016 (3)
C11B	0.055 (3)	0.034 (3)	0.046 (3)	−0.013 (2)	0.000 (3)	−0.014 (2)
O1B	0.081 (3)	0.070 (3)	0.066 (3)	−0.029 (2)	0.029 (2)	−0.044 (2)
C4B	0.056 (4)	0.055 (3)	0.053 (3)	−0.026 (3)	0.004 (3)	−0.021 (3)
C10B	0.050 (3)	0.044 (3)	0.047 (3)	−0.015 (3)	0.011 (2)	−0.021 (2)
C2B	0.054 (3)	0.067 (4)	0.042 (3)	−0.031 (3)	0.011 (2)	−0.030 (3)
O3B	0.139 (5)	0.087 (3)	0.065 (3)	−0.066 (3)	0.032 (3)	−0.048 (3)
C3B	0.073 (4)	0.066 (4)	0.059 (4)	−0.036 (3)	0.009 (3)	−0.039 (3)

Geometric parameters (Å, º) top

C1A—C2A	1.384 (7)	C1B—C2B	1.387 (7)
C1A—C6A	1.389 (7)	C1B—C6B	1.392 (7)
C1A—N1A	1.416 (6)	C1B—N1B	1.421 (6)
N1A—C7A	1.296 (6)	N1B—C7B	1.294 (6)
N1A—H1A	0.8600	N1B—H1B	0.8600
C8A—C9A	1.406 (7)	C8B—C9B	1.408 (7)
C8A—C13A	1.406 (7)	C8B—C13B	1.411 (6)
C8A—C7A	1.412 (7)	C8B—C7B	1.412 (6)
O2A—C13A	1.291 (6)	C13B—O2B	1.296 (6)
C5A—C4A	1.381 (7)	C13B—C12B	1.406 (7)
C5A—C6A	1.391 (7)	C12B—O3B	1.348 (6)
C5A—H5A	0.9300	C12B—C11B	1.363 (7)
O1A—C6A	1.353 (6)	C7B—H7B	0.9300
O1A—H1A1	0.8200	C6B—O1B	1.347 (6)
C13A—C12A	1.416 (7)	C6B—C5B	1.397 (7)
C7A—H7A	0.9300	C9B—C10B	1.362 (7)
C9A—C10A	1.373 (8)	C9B—H9B	0.9300
C9A—H9A	0.9300	C5B—C4B	1.380 (8)
C4A—C3A	1.372 (8)	C5B—H5B	0.9300
C4A—H4A	0.9300	C11B—C10B	1.404 (7)
C12A—C11A	1.358 (8)	C11B—H11B	0.9300
C12A—O3A	1.361 (7)	O1B—H1B1	0.8200
C11A—C10A	1.404 (8)	C4B—C3B	1.375 (8)
C11A—H11A	0.9300	C4B—H4B	0.9300
C10A—H10A	0.9300	C10B—H10B	0.9300
C2A—C3A	1.395 (7)	C2B—C3B	1.395 (7)
C2A—H2A	0.9300	C2B—H2B	0.9300
C3A—H3A	0.9300	O3B—H33B	0.8200
O3A—H33A	0.8200	C3B—H3B	0.9300

C2A—C1A—C6A	119.8 (5)	C2B—C1B—C6B	120.4 (4)
C2A—C1A—N1A	122.4 (4)	C2B—C1B—N1B	122.0 (5)
C6A—C1A—N1A	117.9 (4)	C6B—C1B—N1B	117.6 (4)
C7A—N1A—C1A	127.4 (4)	C7B—N1B—C1B	126.6 (4)
C7A—N1A—H1A	116.3	C7B—N1B—H1B	116.7
C1A—N1A—H1A	116.3	C1B—N1B—H1B	116.7
C9A—C8A—C13A	122.0 (5)	C9B—C8B—C13B	120.2 (4)
C9A—C8A—C7A	118.6 (5)	C9B—C8B—C7B	118.8 (4)
C13A—C8A—C7A	119.4 (5)	C13B—C8B—C7B	121.0 (5)
C4A—C5A—C6A	119.6 (5)	O2B—C13B—C12B	120.4 (4)
C4A—C5A—H5A	120.2	O2B—C13B—C8B	122.2 (4)
C6A—C5A—H5A	120.2	C12B—C13B—C8B	117.4 (5)
C6A—O1A—H1A1	109.5	O3B—C12B—C11B	120.4 (5)
O1A—C6A—C1A	116.2 (4)	O3B—C12B—C13B	117.8 (5)
O1A—C6A—C5A	123.5 (4)	C11B—C12B—C13B	121.7 (4)
C1A—C6A—C5A	120.2 (4)	N1B—C7B—C8B	124.6 (4)
O2A—C13A—C8A	124.2 (5)	N1B—C7B—H7B	117.7
O2A—C13A—C12A	119.9 (5)	C8B—C7B—H7B	117.7
C8A—C13A—C12A	116.0 (5)	O1B—C6B—C1B	115.9 (5)
N1A—C7A—C8A	126.2 (5)	O1B—C6B—C5B	124.3 (5)
N1A—C7A—H7A	116.9	C1B—C6B—C5B	119.8 (5)
C8A—C7A—H7A	116.9	C10B—C9B—C8B	120.6 (4)
C10A—C9A—C8A	119.2 (5)	C10B—C9B—H9B	119.7
C10A—C9A—H9A	120.4	C8B—C9B—H9B	119.7
C8A—C9A—H9A	120.4	C4B—C5B—C6B	119.6 (5)
C3A—C4A—C5A	120.4 (5)	C4B—C5B—H5B	120.2
C3A—C4A—H4A	119.8	C6B—C5B—H5B	120.2
C5A—C4A—H4A	119.8	C12B—C11B—C10B	120.3 (5)
C11A—C12A—O3A	119.0 (5)	C12B—C11B—H11B	119.8
C11A—C12A—C13A	122.3 (5)	C10B—C11B—H11B	119.8
O3A—C12A—C13A	118.5 (5)	C6B—O1B—H1B1	109.5
C12A—C11A—C10A	120.2 (5)	C3B—C4B—C5B	120.5 (5)
C12A—C11A—H11A	119.9	C3B—C4B—H4B	119.7
C10A—C11A—H11A	119.9	C5B—C4B—H4B	119.7
C9A—C10A—C11A	120.0 (5)	C9B—C10B—C11B	119.7 (5)
C9A—C10A—H10A	120.0	C9B—C10B—H10B	120.2
C11A—C10A—H10A	120.0	C11B—C10B—H10B	120.2
C1A—C2A—C3A	119.6 (5)	C1B—C2B—C3B	119.1 (5)
C1A—C2A—H2A	120.2	C1B—C2B—H2B	120.5
C3A—C2A—H2A	120.2	C3B—C2B—H2B	120.5
C4A—C3A—C2A	120.4 (5)	C12B—O3B—H33B	109.5
C4A—C3A—H3A	119.8	C4B—C3B—C2B	120.6 (5)
C2A—C3A—H3A	119.8	C4B—C3B—H3B	119.7
C12A—O3A—H33A	109.5	C2B—C3B—H3B	119.7

C2A—C1A—N1A—C7A	8.2 (8)	C2B—C1B—N1B—C7B	9.4 (8)
C6A—C1A—N1A—C7A	−170.7 (5)	C6B—C1B—N1B—C7B	−168.5 (5)
C2A—C1A—C6A—O1A	−176.5 (5)	C9B—C8B—C13B—O2B	−176.6 (5)
N1A—C1A—C6A—O1A	2.4 (7)	C7B—C8B—C13B—O2B	4.3 (7)
C2A—C1A—C6A—C5A	1.3 (7)	C9B—C8B—C13B—C12B	3.8 (7)
N1A—C1A—C6A—C5A	−179.8 (4)	C7B—C8B—C13B—C12B	−175.3 (5)
C4A—C5A—C6A—O1A	177.4 (5)	O2B—C13B—C12B—O3B	0.0 (8)
C4A—C5A—C6A—C1A	−0.2 (8)	C8B—C13B—C12B—O3B	179.6 (5)
C9A—C8A—C13A—O2A	−176.2 (5)	O2B—C13B—C12B—C11B	176.3 (5)
C7A—C8A—C13A—O2A	4.7 (8)	C8B—C13B—C12B—C11B	−4.1 (8)
C9A—C8A—C13A—C12A	4.0 (7)	C1B—N1B—C7B—C8B	−179.5 (5)
C7A—C8A—C13A—C12A	−175.2 (5)	C9B—C8B—C7B—N1B	−178.9 (5)
C1A—N1A—C7A—C8A	179.9 (5)	C13B—C8B—C7B—N1B	0.2 (7)
C9A—C8A—C7A—N1A	−179.4 (5)	C2B—C1B—C6B—O1B	−176.7 (5)
C13A—C8A—C7A—N1A	−0.3 (8)	N1B—C1B—C6B—O1B	1.3 (7)
C13A—C8A—C9A—C10A	−0.5 (8)	C2B—C1B—C6B—C5B	2.5 (8)
C7A—C8A—C9A—C10A	178.6 (5)	N1B—C1B—C6B—C5B	−179.6 (4)
C6A—C5A—C4A—C3A	−0.6 (8)	C13B—C8B—C9B—C10B	−1.1 (7)
O2A—C13A—C12A—C11A	175.5 (5)	C7B—C8B—C9B—C10B	178.0 (5)
C8A—C13A—C12A—C11A	−4.6 (8)	O1B—C6B—C5B—C4B	177.5 (5)
O2A—C13A—C12A—O3A	0.4 (9)	C1B—C6B—C5B—C4B	−1.6 (8)
C8A—C13A—C12A—O3A	−179.8 (5)	O3B—C12B—C11B—C10B	177.9 (5)
O3A—C12A—C11A—C10A	177.0 (6)	C13B—C12B—C11B—C10B	1.6 (8)
C13A—C12A—C11A—C10A	1.9 (9)	C6B—C5B—C4B—C3B	0.1 (9)
C8A—C9A—C10A—C11A	−2.5 (8)	C8B—C9B—C10B—C11B	−1.5 (8)
C12A—C11A—C10A—C9A	1.8 (9)	C12B—C11B—C10B—C9B	1.3 (8)
C6A—C1A—C2A—C3A	−1.7 (8)	C6B—C1B—C2B—C3B	−1.9 (8)
N1A—C1A—C2A—C3A	179.5 (5)	N1B—C1B—C2B—C3B	−179.8 (5)
C5A—C4A—C3A—C2A	0.2 (9)	C5B—C4B—C3B—C2B	0.5 (10)
C1A—C2A—C3A—C4A	0.9 (9)	C1B—C2B—C3B—C4B	0.4 (9)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N1A—H1A···O2A	0.86	1.98	2.655 (5)	134
O1A—H1A1···O2B	0.82	1.85	2.664 (5)	174
O3A—H33A···O2A	0.82	2.27	2.710 (6)	114
N1B—H1B···O2B	0.86	1.96	2.637 (5)	135
O3B—H33B···O2B	0.82	2.25	2.694 (6)	115
O1B—H1B1···O2Aⁱ	0.82	1.84	2.658 (6)	176

Symmetry code: (i) x−1, y, z.

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