(3-Hy­droxy­piperidin-1-yl)(4-methyl­phen­yl)methanone

In the title mol­ecule, C₁₃H₁₇NO₂, the piperidine ring assumes a chair conformation. The dihedral angle between the mean plane of the piperidine ring and the benzene ring is 45.49 (1)°. In the crystal, mol­ecules are linked by O—H...O inter­molecular hydrogen bonds, leading to a mol­ecular chain running along the c-axis direction. The atoms of the hy­droxy piperidine ring and the methyl group of methyl­phenyl ring are disordered over two sets of sites with refined occupancies of 0.754 (5) and 0.246 (5).

Key indicators

• Single-crystal X-ray study
• T = 293 K
• Mean [sigma](C-C) = 0.003 Å
• Disorder in main residue
• R factor = 0.039
• wR factor = 0.099
• Data-to-parameter ratio = 10.4

checkCIF/PLATON results

No syntax errors found



Alert level C
PLAT089_ALERT_3_C Poor Data / Parameter Ratio (Zmax < 18) ........       5.56 Note
PLAT213_ALERT_2_C Atom C1'             has ADP max/min Ratio .....        3.1 oblate
PLAT230_ALERT_2_C Hirshfeld Test Diff for    C2     --  C7      ..        6.0 s.u.
PLAT242_ALERT_2_C Low    'MainMol' Ueq as Compared to Neighbors of         C2 Check
PLAT250_ALERT_2_C Large U3/U1 Ratio for Average U(i,j) Tensor ....        2.2 Note
PLAT309_ALERT_2_C Single Bonded Oxygen (C-O > 1.3 Ang) ...........        O1' Check
PLAT480_ALERT_4_C Long H...A H-Bond Reported H9B    ..  O1      ..       2.66 Ang.
PLAT911_ALERT_3_C Missing # FCF Refl Between THmin & STh/L=  0.600          6 Report
PLAT913_ALERT_3_C Missing # of Very Strong Reflections in FCF ....          5 Note
PLAT934_ALERT_3_C Number of (Iobs-Icalc)/SigmaW > 10 Outliers ....          1 Check
PLAT978_ALERT_2_C Number C-C Bonds with Positive Residual Density.          0 Info

Alert level G
PLAT002_ALERT_2_G Number of Distance or Angle Restraints on AtSite         15 Note
PLAT003_ALERT_2_G Number of Uiso or Uij Restrained non-H Atoms ...         16 Report
PLAT005_ALERT_5_G No Embedded Refinement Details found  in the CIF     Please Do !
PLAT007_ALERT_5_G Number of Unrefined Donor-H Atoms ..............          2 Report
PLAT032_ALERT_4_G Std. Uncertainty on Flack Parameter Value High .      0.500 Report
PLAT066_ALERT_1_G Predicted and Reported Tmin&Tmax Range Identical          ? Check
PLAT199_ALERT_1_G Reported _cell_measurement_temperature ..... (K)        293 Check
PLAT200_ALERT_1_G Reported   _diffrn_ambient_temperature ..... (K)        293 Check
PLAT301_ALERT_3_G Main Residue  Disorder ..............(Resd  1)..        56% Note
PLAT720_ALERT_4_G Number of Unusual/Non-Standard Labels ..........          5 Note
PLAT779_ALERT_4_G Suspect or Irrelevant (Bond) Angle in CIF .... #         17 Check
              O1   -C8   -O1'     1.555   1.555   1.555             11.40 Deg.
PLAT779_ALERT_4_G Suspect or Irrelevant (Bond) Angle in CIF .... #         20 Check
              N1   -C8   -N1'     1.555   1.555   1.555             36.80 Deg.
PLAT779_ALERT_4_G Suspect or Irrelevant (Bond) Angle in CIF .... #         31 Check
              C1   -C2   -C1'     1.555   1.555   1.555              8.10 Deg.
PLAT792_ALERT_1_G The Model has Chirality at C12     (Polar  SPGR)          S Verify
PLAT811_ALERT_5_G No ADDSYM Analysis: Too Many Excluded Atoms ....          ! Info
PLAT860_ALERT_3_G Number of Least-Squares Restraints .............         99 Note
PLAT899_ALERT_4_G SHELXL97   is Deprecated and Succeeded by SHELXL       2016 Note
PLAT910_ALERT_3_G Missing # of FCF Reflection(s) Below Theta(Min).          2 Note
PLAT916_ALERT_2_G Hooft y and Flack x Parameter values differ by .       0.13 Check

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

   4 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
   7 ALERT type 3 Indicator that the structure quality may be low
   7 ALERT type 4 Improvement, methodology, query or suggestion
   3 ALERT type 5 Informative message, check

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Computing details

Data collection: APEX2 (Bruker , 2004); cell refinement: APEX2 and SAINT (Bruker, 2004); data reduction: SAINT and XPREP (Bruker, 2004); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 for Windows (Farrugia, 2012); software used to prepare material for publication: SHELXL97 (Sheldrick, 2008).

(3-Hydroxypiperidin-1-yl)(4-methylphenyl)methanone

Crystal data

C13H17NO2	F(000) = 472
Mr = 219.28	Dx = 1.207 Mg m^−3
Orthorhombic, Pca21	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2c -2ac	Cell parameters from 2385 reflections
a = 24.8766 (14) Å	θ = 0.8–0.7°
b = 6.1117 (4) Å	µ = 0.08 mm^−1
c = 7.9388 (4) Å	T = 293 K
V = 1207.00 (12) Å^3	Block, yellow
Z = 4	0.30 × 0.25 × 0.20 mm

Data collection

Bruker Kappa APEXII CCD diffractometer	2385 independent reflections
Radiation source: fine-focus sealed tube	1692 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.055
ω and \ f scan	θmax = 26.0°, θmin = 3.3°
Absorption correction: multi-scan (SADABS; Bruker, 2004)	h = −30→30
Tmin = 0.976, Tmax = 0.984	k = −7→7
20282 measured reflections	l = −9→9

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)] = 0.039	w = 1/[σ^2(Fo^2) + (0.0468P)^2 + 0.0531P] where P = (Fo^2 + 2Fc^2)/3
wR(F^2) = 0.099	(Δ/σ)max < 0.001
S = 1.11	Δρmax = 0.13 e Å^−3
2385 reflections	Δρmin = −0.11 e Å^−3
230 parameters	Extinction correction: SHELXL97 (Sheldrick, 2008), Fc^*=kFc[1+0.001xFc^2λ^3/sin(2θ)]^-1/4
99 restraints	Extinction coefficient: 0.141 (11)
Primary atom site location: structure-invariant direct methods	Absolute structure: Flack x determined using 675 quotients [(I+)-(I-)]/[(I+)+(I-)] (Parsons et al. (2013)
Secondary atom site location: difference Fourier map	Absolute structure parameter: 0.3 (5)

Special details

Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds 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 > 2sigma(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.

H atoms were positioned geometrically and treated as riding on their parent atoms and refined with, C—H distance of 0.93–0.98 Å, O—H of 0.82 Å with U_iso(H)= 1.5 U_eq(c-methyl),and U_iso(H)= 1.2Ueq(C) for other H atoms.

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

	x	y	z	Uiso*/Ueq	Occ. (<1)
C3	0.18222 (11)	−0.4020 (4)	1.0752 (3)	0.0762 (7)
H3	0.1791	−0.5388	1.1256	0.091*
C4	0.13647 (8)	−0.2764 (3)	1.0519 (3)	0.0670 (6)
H4	0.1032	−0.3274	1.0885	0.080*
C5	0.14041 (8)	−0.0763 (3)	0.9743 (2)	0.0576 (5)
C6	0.19040 (9)	−0.0040 (4)	0.9234 (3)	0.0701 (6)
H6	0.1935	0.1314	0.8708	0.084*
C7	0.23570 (8)	−0.1285 (4)	0.9492 (3)	0.0748 (6)
H7	0.2690	−0.0765	0.9145	0.090*
C8	0.09139 (9)	0.0653 (3)	0.9589 (3)	0.0666 (6)
C2	0.23190 (9)	−0.3301 (4)	1.0261 (3)	0.0733 (7)
C1	0.2817 (3)	−0.4667 (13)	1.0622 (13)	0.116 (3)	0.754 (5)
H1A	0.3073	−0.4472	0.9729	0.174*	0.754 (5)
H1B	0.2719	−0.6183	1.0694	0.174*	0.754 (5)
H1C	0.2974	−0.4208	1.1669	0.174*	0.754 (5)
C9	0.02203 (13)	0.2386 (6)	0.7818 (4)	0.0590 (8)	0.754 (5)
H9A	0.0114	0.2993	0.8897	0.071*	0.754 (5)
H9B	−0.0085	0.1612	0.7347	0.071*	0.754 (5)
C10	0.03892 (17)	0.4199 (6)	0.6648 (5)	0.0643 (10)	0.754 (5)
H10A	0.0666	0.5071	0.7187	0.077*	0.754 (5)
H10B	0.0084	0.5144	0.6428	0.077*	0.754 (5)
C11	0.06016 (18)	0.3312 (8)	0.4998 (5)	0.0669 (12)	0.754 (5)
H11A	0.0312	0.2601	0.4389	0.080*	0.754 (5)
H11B	0.0734	0.4511	0.4313	0.080*	0.754 (5)
C12	0.10493 (16)	0.1694 (7)	0.5298 (4)	0.0621 (9)	0.754 (5)
H12	0.1339	0.2492	0.5867	0.075*	0.754 (5)
C13	0.08638 (13)	−0.0078 (5)	0.6499 (3)	0.0529 (8)	0.754 (5)
H13A	0.0579	−0.0923	0.5978	0.063*	0.754 (5)
H13B	0.1160	−0.1060	0.6740	0.063*	0.754 (5)
N1	0.06702 (11)	0.0872 (5)	0.8051 (3)	0.0498 (7)	0.754 (5)
O1	0.0701 (2)	0.1339 (12)	1.0822 (7)	0.0802 (15)	0.754 (5)
O2	0.12710 (16)	0.0789 (9)	0.3835 (4)	0.1091 (16)	0.754 (5)
H2	0.1118	0.1294	0.3007	0.164*	0.754 (5)
C1'	0.2820 (6)	−0.480 (4)	1.037 (3)	0.095 (7)	0.246 (5)
H1'1	0.3139	−0.3949	1.0188	0.142*	0.246 (5)
H1'2	0.2796	−0.5919	0.9519	0.142*	0.246 (5)
H1'3	0.2835	−0.5473	1.1460	0.142*	0.246 (5)
C9'	0.0545 (5)	0.363 (2)	0.7878 (13)	0.081 (4)	0.246 (5)
H9'1	0.0743	0.4953	0.7602	0.097*	0.246 (5)
H9'2	0.0362	0.3883	0.8940	0.097*	0.246 (5)
C10'	0.0136 (5)	0.325 (3)	0.6554 (15)	0.081 (4)	0.246 (5)
H10C	−0.0066	0.4583	0.6364	0.097*	0.246 (5)
H10D	−0.0114	0.2131	0.6933	0.097*	0.246 (5)
C11'	0.0396 (6)	0.251 (3)	0.4900 (19)	0.087 (5)	0.246 (5)
H11C	0.0121	0.2065	0.4106	0.104*	0.246 (5)
H11D	0.0596	0.3717	0.4407	0.104*	0.246 (5)
C12'	0.0770 (6)	0.062 (2)	0.5267 (15)	0.083 (4)	0.246 (5)
H12'	0.0547	−0.0547	0.5744	0.100*	0.246 (5)
C13'	0.1182 (4)	0.1118 (19)	0.6524 (12)	0.071 (3)	0.246 (5)
H13C	0.1417	0.2262	0.6103	0.085*	0.246 (5)
H13D	0.1398	−0.0174	0.6734	0.085*	0.246 (5)
N1'	0.0927 (4)	0.1837 (17)	0.8095 (9)	0.064 (3)	0.246 (5)
O1'	0.0737 (10)	0.179 (4)	1.098 (3)	0.110 (8)	0.246 (5)
O2'	0.1012 (5)	−0.0230 (18)	0.3875 (13)	0.084 (3)	0.246 (5)
H2'	0.0802	−0.0193	0.3079	0.126*	0.246 (5)

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
C3	0.1035 (19)	0.0606 (13)	0.0644 (13)	0.0231 (12)	−0.0065 (13)	0.0065 (11)
C4	0.0729 (13)	0.0679 (14)	0.0601 (12)	0.0152 (10)	0.0062 (10)	0.0074 (10)
C5	0.0705 (13)	0.0611 (12)	0.0413 (9)	0.0178 (10)	0.0010 (9)	0.0032 (9)
C6	0.0805 (14)	0.0612 (11)	0.0686 (14)	0.0120 (11)	0.0052 (11)	0.0074 (10)
C7	0.0665 (13)	0.0795 (16)	0.0784 (14)	0.0045 (12)	−0.0032 (12)	−0.0057 (12)
C8	0.0769 (13)	0.0750 (14)	0.0477 (11)	0.0262 (11)	0.0040 (11)	0.0086 (10)
C2	0.0765 (16)	0.0815 (16)	0.0618 (14)	0.0287 (13)	−0.0157 (11)	−0.0186 (12)
C1	0.126 (6)	0.120 (6)	0.100 (5)	0.078 (5)	−0.028 (3)	−0.044 (4)
C9	0.0543 (17)	0.071 (2)	0.0519 (17)	0.0210 (15)	0.0023 (13)	0.0046 (14)
C10	0.075 (2)	0.059 (2)	0.059 (2)	0.0239 (16)	−0.0076 (18)	0.0038 (17)
C11	0.075 (3)	0.080 (2)	0.0464 (19)	0.0186 (19)	−0.0010 (17)	0.0135 (17)
C12	0.062 (2)	0.086 (2)	0.0380 (16)	0.0183 (17)	0.0000 (13)	0.0011 (16)
C13	0.0557 (16)	0.0535 (17)	0.0494 (16)	0.0130 (14)	−0.0132 (12)	−0.0121 (13)
N1	0.0508 (15)	0.0529 (15)	0.0457 (12)	0.0118 (12)	−0.0007 (11)	0.0038 (11)
O1	0.082 (2)	0.119 (4)	0.040 (2)	0.046 (2)	0.0107 (16)	0.002 (2)
O2	0.096 (3)	0.186 (5)	0.0448 (12)	0.071 (3)	0.0066 (16)	−0.003 (2)
C1'	0.041 (8)	0.153 (18)	0.090 (12)	0.015 (7)	−0.032 (7)	0.037 (11)
C9'	0.097 (8)	0.083 (7)	0.062 (6)	0.046 (6)	−0.020 (5)	−0.015 (5)
C10'	0.077 (8)	0.108 (9)	0.058 (6)	0.033 (6)	−0.016 (6)	−0.015 (7)
C11'	0.092 (9)	0.108 (10)	0.060 (6)	0.050 (8)	−0.019 (6)	−0.009 (7)
C12'	0.096 (8)	0.093 (8)	0.062 (6)	0.043 (7)	−0.019 (6)	−0.019 (6)
C13'	0.079 (7)	0.069 (6)	0.064 (6)	0.016 (6)	0.007 (5)	0.000 (5)
N1'	0.075 (6)	0.076 (6)	0.040 (4)	0.028 (5)	−0.014 (4)	−0.015 (4)
O1'	0.188 (15)	0.085 (8)	0.057 (8)	0.075 (8)	−0.027 (7)	−0.036 (6)
O2'	0.100 (8)	0.097 (7)	0.054 (4)	0.045 (5)	−0.003 (5)	−0.024 (4)

Geometric parameters (Å, º)

C3—C2	1.368 (3)	C11—H11B	0.9700
C3—C4	1.385 (3)	C12—O2	1.399 (5)
C3—H3	0.9300	C12—C13	1.515 (5)
C4—C5	1.373 (3)	C12—H12	0.9800
C4—H4	0.9300	C13—N1	1.444 (3)
C5—C6	1.380 (3)	C13—H13A	0.9700
C5—C8	1.500 (3)	C13—H13B	0.9700
C6—C7	1.375 (3)	O2—H2	0.8200
C6—H6	0.9300	C1'—H1'1	0.9600
C7—C2	1.379 (3)	C1'—H1'2	0.9600
C7—H7	0.9300	C1'—H1'3	0.9600
C8—O1	1.189 (5)	C9'—N1'	1.463 (11)
C8—N1	1.370 (3)	C9'—C10'	1.481 (14)
C8—O1'	1.37 (2)	C9'—H9'1	0.9700
C8—N1'	1.390 (9)	C9'—H9'2	0.9700
C2—C1	1.522 (5)	C10'—C11'	1.531 (15)
C2—C1'	1.551 (13)	C10'—H10C	0.9700
C1—H1A	0.9600	C10'—H10D	0.9700
C1—H1B	0.9600	C11'—C12'	1.512 (14)
C1—H1C	0.9600	C11'—H11C	0.9700
C9—N1	1.464 (3)	C11'—H11D	0.9700
C9—C10	1.506 (5)	C12'—O2'	1.362 (15)
C9—H9A	0.9700	C12'—C13'	1.463 (14)
C9—H9B	0.9700	C12'—H12'	0.9800
C10—C11	1.513 (5)	C13'—N1'	1.467 (11)
C10—H10A	0.9700	C13'—H13C	0.9700
C10—H10B	0.9700	C13'—H13D	0.9700
C11—C12	1.508 (5)	O2'—H2'	0.8200
C11—H11A	0.9700
C2—C3—C4	121.7 (2)	C11—C12—C13	110.1 (3)
C2—C3—H3	119.1	O2—C12—H12	106.8
C4—C3—H3	119.1	C11—C12—H12	106.8
C5—C4—C3	119.7 (2)	C13—C12—H12	106.8
C5—C4—H4	120.2	N1—C13—C12	110.6 (3)
C3—C4—H4	120.2	N1—C13—H13A	109.5
C4—C5—C6	118.73 (18)	C12—C13—H13A	109.5
C4—C5—C8	119.50 (18)	N1—C13—H13B	109.5
C6—C5—C8	121.60 (18)	C12—C13—H13B	109.5
C7—C6—C5	121.2 (2)	H13A—C13—H13B	108.1
C7—C6—H6	119.4	C8—N1—C13	125.0 (2)
C5—C6—H6	119.4	C8—N1—C9	120.8 (2)
C6—C7—C2	120.3 (2)	C13—N1—C9	113.7 (2)
C6—C7—H7	119.9	C12—O2—H2	109.5
C2—C7—H7	119.9	C2—C1'—H1'1	109.5
O1—C8—N1	120.1 (3)	C2—C1'—H1'2	109.5
O1—C8—O1'	11.4 (14)	H1'1—C1'—H1'2	109.5
N1—C8—O1'	121.5 (11)	C2—C1'—H1'3	109.5
O1—C8—N1'	121.9 (5)	H1'1—C1'—H1'3	109.5
N1—C8—N1'	36.8 (4)	H1'2—C1'—H1'3	109.5
O1'—C8—N1'	115.3 (11)	N1'—C9'—C10'	114.2 (9)
O1—C8—C5	119.9 (3)	N1'—C9'—H9'1	108.7
N1—C8—C5	119.25 (19)	C10'—C9'—H9'1	108.7
O1'—C8—C5	119.2 (11)	N1'—C9'—H9'2	108.7
N1'—C8—C5	110.5 (4)	C10'—C9'—H9'2	108.7
C3—C2—C7	118.40 (19)	H9'1—C9'—H9'2	107.6
C3—C2—C1	120.4 (5)	C9'—C10'—C11'	111.4 (10)
C7—C2—C1	121.2 (5)	C9'—C10'—H10C	109.3
C3—C2—C1'	121.3 (9)	C11'—C10'—H10C	109.3
C7—C2—C1'	119.9 (9)	C9'—C10'—H10D	109.3
C1—C2—C1'	8.1 (13)	C11'—C10'—H10D	109.3
C2—C1—H1A	109.5	H10C—C10'—H10D	108.0
C2—C1—H1B	109.5	C12'—C11'—C10'	108.5 (11)
C2—C1—H1C	109.5	C12'—C11'—H11C	110.0
N1—C9—C10	109.2 (2)	C10'—C11'—H11C	110.0
N1—C9—H9A	109.8	C12'—C11'—H11D	110.0
C10—C9—H9A	109.8	C10'—C11'—H11D	110.0
N1—C9—H9B	109.8	H11C—C11'—H11D	108.4
C10—C9—H9B	109.8	O2'—C12'—C13'	108.8 (10)
H9A—C9—H9B	108.3	O2'—C12'—C11'	114.1 (11)
C9—C10—C11	111.6 (3)	C13'—C12'—C11'	113.8 (11)
C9—C10—H10A	109.3	O2'—C12'—H12'	106.5
C11—C10—H10A	109.3	C13'—C12'—H12'	106.5
C9—C10—H10B	109.3	C11'—C12'—H12'	106.5
C11—C10—H10B	109.3	C12'—C13'—N1'	109.8 (8)
H10A—C10—H10B	108.0	C12'—C13'—H13C	109.7
C12—C11—C10	110.9 (3)	N1'—C13'—H13C	109.7
C12—C11—H11A	109.5	C12'—C13'—H13D	109.7
C10—C11—H11A	109.5	N1'—C13'—H13D	109.7
C12—C11—H11B	109.5	H13C—C13'—H13D	108.2
C10—C11—H11B	109.5	C8—N1'—C9'	118.4 (8)
H11A—C11—H11B	108.1	C8—N1'—C13'	125.4 (7)
O2—C12—C11	114.8 (3)	C9'—N1'—C13'	114.0 (8)
O2—C12—C13	111.1 (3)	C12'—O2'—H2'	109.5
C2—C3—C4—C5	1.4 (3)	N1'—C8—N1—C13	82.2 (6)
C3—C4—C5—C6	−0.9 (3)	C5—C8—N1—C13	−3.4 (4)
C3—C4—C5—C8	−176.20 (19)	O1—C8—N1—C9	15.1 (6)
C4—C5—C6—C7	0.0 (3)	O1'—C8—N1—C9	1.9 (13)
C8—C5—C6—C7	175.2 (2)	N1'—C8—N1—C9	−89.1 (6)
C5—C6—C7—C2	0.3 (3)	C5—C8—N1—C9	−174.6 (2)
C4—C5—C8—O1	63.9 (5)	C12—C13—N1—C8	−112.6 (4)
C6—C5—C8—O1	−111.3 (5)	C12—C13—N1—C9	59.2 (4)
C4—C5—C8—N1	−106.4 (3)	C10—C9—N1—C8	114.0 (4)
C6—C5—C8—N1	78.4 (3)	C10—C9—N1—C13	−58.2 (4)
C4—C5—C8—O1'	77.0 (13)	N1'—C9'—C10'—C11'	−50.2 (19)
C6—C5—C8—O1'	−98.2 (12)	C9'—C10'—C11'—C12'	51.2 (19)
C4—C5—C8—N1'	−146.0 (5)	C10'—C11'—C12'—O2'	177.8 (13)
C6—C5—C8—N1'	38.8 (6)	C10'—C11'—C12'—C13'	−56.6 (19)
C4—C3—C2—C7	−1.1 (3)	O2'—C12'—C13'—N1'	−174.5 (10)
C4—C3—C2—C1	176.7 (4)	C11'—C12'—C13'—N1'	57.1 (17)
C4—C3—C2—C1'	−174.0 (12)	O1—C8—N1'—C9'	−18.1 (12)
C6—C7—C2—C3	0.2 (3)	N1—C8—N1'—C9'	80.7 (10)
C6—C7—C2—C1	−177.6 (4)	O1'—C8—N1'—C9'	−28.7 (16)
C6—C7—C2—C1'	173.2 (12)	C5—C8—N1'—C9'	−167.5 (8)
N1—C9—C10—C11	54.8 (5)	O1—C8—N1'—C13'	179.8 (9)
C9—C10—C11—C12	−54.5 (5)	N1—C8—N1'—C13'	−81.4 (10)
C10—C11—C12—O2	−179.9 (4)	O1'—C8—N1'—C13'	169.2 (14)
C10—C11—C12—C13	53.9 (5)	C5—C8—N1'—C13'	30.3 (12)
O2—C12—C13—N1	176.0 (3)	C10'—C9'—N1'—C8	−112.8 (14)
C11—C12—C13—N1	−55.7 (4)	C10'—C9'—N1'—C13'	51.3 (17)
O1—C8—N1—C13	−173.6 (5)	C12'—C13'—N1'—C8	109.9 (14)
O1'—C8—N1—C13	173.2 (13)	C12'—C13'—N1'—C9'	−52.9 (14)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
C9—H9B···O1^i	0.97	2.66	3.598 (7)	163
O2—H2···O1^ii	0.82	2.02	2.802 (7)	159
O2′—H2′···O1′^ii	0.82	2.07	2.70 (3)	134

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