The amino alcohol MeN(CH2CMe2OH)2

Lutter, M.; Gock, V.; Jurkschat, K.

doi:10.1107/S2414314617007994

organic compounds

IUCrDATA

ISSN: 2414-3146

Volume 2| Part 6| June 2017| x170799

https://doi.org/10.1107/S2414314617007994

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The amino alcohol MeN(CH₂CMe₂OH)₂

Michael Lutter,^a Vinusuya Gock ^a and Klaus Jurkschat ^a ^*

^aLehrstuhl für Anorganische Chemie II, Technische Universität Dortmund, Otto-Hahn-Strasse 6, 44221 Dortmund, Germany
^*Correspondence e-mail: klaus.jurkschat@tu-dortmund.de

Edited by M. Bolte, Goethe-Universität Frankfurt, Germany (Received 25 May 2017; accepted 30 May 2017; online 2 June 2017)

The crystal structure, including a graph-set analysis, of 1-[(2-hydroxy-2-methylpropyl)methylamino]-2-methylpropan-2-ol, C₉H₂₁NO₂, is reported. The structure is characterized by unsymmetrical intra- and intermolecular O—H⋯O hydrogen bridges, giving rise to the formation of an infinite polymer consisting of eight-membered rings arranged in zigzag chains running along the a axis.

Keywords: crystal structure; amino alcohol; graph set analysis; hydrogen bridge.

CCDC reference: 1551877

Structure description

Amino alcohols are an important industrial commodity with widespread applications. Some representatives of these compounds have also characterized by single-crystal X-ray diffraction analysis (Churakov et al., 2009 ). In the context with our long-standing interest in tin and silicon derivatives of amino alcohols (Berends et al., 2009 ; Glowacki et al., 2016 , 2017 ; Gock et al., 2013 ; Iovkova-Berends, Zöller, Bradtmöller et al., 2012 ; Iovkova-Berends, Berends, Zöller, Schollmeyer et al., 2012 ; Lutter et al., 2012 ; Zöller et al., 2011 , 2012 ; Zöller & Jurkschat, 2013 ), we report here the crystal structure of the title compound (Fig. 1). The latter crystallizes in the orthorhombic space group Pna2₁ with eight molecules in the unit cell and two molecules in the asymmetric unit. Each of the crystallographic independent molecules shows an intramolecular O—H⋯O hydrogen bridge with O11⋯O17 and O31⋯O37 distances of 2.621 (4) and 2.715 (4) Å, respectively (Table 1). The two eight-membered rings thus formed are linked by an intermolecular O—H⋯O hydrogen bridge with an O11⋯O37 distance of 2.656 (3) Å giving a dimer. The dimers are linked via intermolecular O—H⋯O hydrogen bridges with an O17⋯O31 distance of 2.712 (3) Å, giving an infinite polymer.

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O11—H11⋯O37	0.76 (2)	1.91 (2)	2.656 (3)	168 (5)
O17—H17⋯O11	0.80 (2)	1.84 (2)	2.621 (4)	165 (4)
O31—H31⋯O17ⁱ	0.74 (2)	1.99 (2)	2.712 (3)	165 (4)
O37—H37⋯O31	0.83 (2)	1.89 (2)	2.715 (4)	174 (4)
Symmetry code: (i) $[x+{\script{1\over 2}}, -y+{\script{1\over 2}}, z]$ .

Figure 1
The molecular structure of MeN(CH₂CMe₂OH)₂, showing 30% probability displacement ellipsoids and the atom-numbering scheme. H atoms bonded to C atoms have been omitted for clarity. Hydrogen bonds are drawn as dashed lines.

The structure resembles those of Ph(Me)(H)CN(CH₂CMe₂OH)₂ (Churakov et al., 2009) and p-FC₆H₄N(CH₂CMe₂OH)₂ (Lutter et al., 2012). A graph-set analysis according to Etter and Bernstein (Bernstein et al., 1990 , 1995 ; Bernstein, 1991 ; Etter, 1990 , 1991 ; Etter et al., 1990 ) gives the unitary graph set N₁ = S(8)DS(8)D.

Synthesis and crystallization

The synthesis and the chemical and physical properties of the title compound were published by Hong et al. (2008 ). The latter crystallizes from the melt as colourless column-shaped crystals.

Refinement

Crystal data, data collection and structure refinement details are summarized in Table 2. The crystal structure exhibits pseudo symmetry with a percentage fit of 83% for the higher symmetry space group Pbcn. However, refinement in the space group Pbcn is non-satisfactory.

Table 2
Experimental details

Crystal data
Chemical formula	C₉H₂₁NO₂
M_r	175.27
Crystal system, space group	Orthorhombic, Pna2₁
Temperature (K)	173
a, b, c (Å)	14.152 (2), 9.8983 (16), 15.9939 (19)
V (Å³)	2240.5 (5)
Z	8
Radiation type	Mo Kα
μ (mm⁻¹)	0.07
Crystal size (mm)	0.40 × 0.19 × 0.06

Data collection
Diffractometer	Oxford Diffraction Xcalibur Sapphire3
Absorption correction	Multi-scan (CrysAlis PRO; Oxford Diffraction, 2006 $[Oxford Diffraction (2006). CrysAlis PRO. Oxford Diffraction Ltd, Abingdon, Oxfordshire, England.]$ )
T_min, T_max	0.872, 1.000
No. of measured, independent and observed [I > 2σ(I)] reflections	8013, 4390, 1763
R_int	0.039
(sin θ/λ)_max (Å⁻¹)	0.650

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.039, 0.045, 0.80
No. of reflections	4390
No. of parameters	239
No. of restraints	5
H-atom treatment	H atoms treated by a mixture of independent and constrained refinement
Δρ_max, Δρ_min (e Å⁻³)	0.13, −0.15
Computer programs: CrysAlis PRO (Oxford Diffraction, 2006 $[Oxford Diffraction (2006). CrysAlis PRO. Oxford Diffraction Ltd, Abingdon, Oxfordshire, England.]$ ), SHELXS (Sheldrick, 2008 ), SHELXL2014 (Sheldrick, 2015 ), ORTEP-3 for Windows (Farrugia, 2012 ) and enCIFer(Allen et al., 2004 ).

Structural data

CCDC reference: 1551877

Crystal structure: contains datablocks global, I. DOI: https://doi.org/10.1107/S2414314617007994/bt4050sup1.cif

Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S2414314617007994/bt4050Isup2.hkl

Supporting information file. DOI: https://doi.org/10.1107/S2414314617007994/bt4050Isup3.cdx

Supporting information file. DOI: https://doi.org/10.1107/S2414314617007994/bt4050Isup4.cml

checkCIF report

Computing details top

Data collection: CrysAlis PRO (Oxford Diffraction, 2006); cell refinement: CrysAlis PRO (Oxford Diffraction, 2006); data reduction: CrysAlis PRO (Oxford Diffraction, 2006); program(s) used to solve structure: SHELXS (Sheldrick, 2008); program(s) used to refine structure: SHELXL2014 (Sheldrick, 2015); molecular graphics: ORTEP-3 for Windows (Farrugia, 2012); software used to prepare material for publication: enCIFer (Allen et al., 2004).

1-[(2-Hydroxy-2-methylpropyl)methylamino]-2-methylpropan-2-ol top

Crystal data top

C₉H₂₁NO₂	D_x = 1.039 Mg m⁻³
M_r = 175.27	Mo Kα radiation, λ = 0.71073 Å
Orthorhombic, Pna2₁	Cell parameters from 1703 reflections
a = 14.152 (2) Å	θ = 2.4–29.2°
b = 9.8983 (16) Å	µ = 0.07 mm⁻¹
c = 15.9939 (19) Å	T = 173 K
V = 2240.5 (5) Å³	Column, colourless
Z = 8	0.40 × 0.19 × 0.06 mm
F(000) = 784

Data collection top

Oxford Diffraction Xcalibur Sapphire3 diffractometer	4390 independent reflections
Graphite monochromator	1763 reflections with I > 2σ(I)
Detector resolution: 16.0560 pixels mm^-1	R_int = 0.039
ω und ψ scan	θ_max = 27.5°, θ_min = 2.4°
Absorption correction: multi-scan (CrysAlis PRO; Oxford Diffraction, 2006)	h = −14→18
T_min = 0.872, T_max = 1.000	k = −12→6
8013 measured reflections	l = −20→18

Refinement top

Refinement on F²	Hydrogen site location: mixed
Least-squares matrix: full	H atoms treated by a mixture of independent and constrained refinement
R[F² > 2σ(F²)] = 0.039	w = 1/[σ²(F_o²) + (0.005P)²] where P = (F_o² + 2F_c²)/3
wR(F²) = 0.045	(Δ/σ)_max = 0.036
S = 0.80	Δρ_max = 0.13 e Å⁻³
4390 reflections	Δρ_min = −0.15 e Å⁻³
239 parameters	Absolute structure: Flack x determined using 585 quotients [(I⁺)-(I^-)]/[(I⁺)+(I^-)] (Parsons et al., 2013).
5 restraints

Special details top

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.

The OH protons were located in the difference Fourier map. Their coordinates were refined using a restraint of O—H = 0.84 (2) Å. The H atoms bonded to C were refined as riding on their parent atom. The U values of all H atoms were set to U_iso(H) = 1.2U_eq(C) or U_iso(H) = 1.5U_eq(C_methyl,O).

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å²) top

	x	y	z	U_iso*/U_eq
O11	0.4659 (2)	0.3733 (3)	0.5278 (2)	0.0561 (9)
H11	0.476 (3)	0.298 (2)	0.522 (3)	0.084*
C12	0.5439 (3)	0.4601 (4)	0.5463 (3)	0.0399 (11)
C13	0.4990 (3)	0.5893 (4)	0.5796 (2)	0.0407 (11)
H13A	0.5490	0.6583	0.5866	0.049*
H13B	0.4537	0.6237	0.5375	0.049*
N14	0.4499 (2)	0.5737 (3)	0.65840 (18)	0.0404 (9)
C14	0.5045 (3)	0.6325 (4)	0.7268 (3)	0.0708 (16)
H14A	0.5671	0.5904	0.7287	0.106*
H14B	0.4716	0.6166	0.7798	0.106*
H14C	0.5113	0.7299	0.7176	0.106*
C15	0.3512 (3)	0.6184 (4)	0.6587 (2)	0.0466 (13)
H15A	0.3439	0.6903	0.6162	0.056*
H15B	0.3373	0.6589	0.7139	0.056*
C16	0.2785 (3)	0.5092 (4)	0.6414 (2)	0.0338 (11)
O17	0.29330 (19)	0.4557 (3)	0.55810 (14)	0.0441 (8)
H17	0.3433 (19)	0.418 (4)	0.554 (2)	0.066*
C18	0.5966 (3)	0.4929 (5)	0.4649 (2)	0.0595 (14)
H18A	0.6225	0.4096	0.4411	0.089*
H18B	0.6482	0.5561	0.4767	0.089*
H18C	0.5526	0.5340	0.4249	0.089*
C19	0.6092 (3)	0.3933 (4)	0.6075 (2)	0.0436 (12)
H19A	0.5750	0.3747	0.6595	0.065*
H19B	0.6627	0.4532	0.6191	0.065*
H19C	0.6324	0.3083	0.5838	0.065*
C20	0.2889 (3)	0.3954 (3)	0.70317 (19)	0.0489 (12)
H20A	0.2439	0.3234	0.6894	0.073*
H20B	0.2761	0.4289	0.7597	0.073*
H20C	0.3534	0.3596	0.7006	0.073*
C21	0.1808 (3)	0.5690 (4)	0.6412 (2)	0.0526 (14)
H21A	0.1346	0.4987	0.6273	0.079*
H21B	0.1774	0.6415	0.5996	0.079*
H21C	0.1665	0.6058	0.6967	0.079*
O31	0.6890 (2)	0.0885 (3)	0.41852 (14)	0.0383 (7)
H31	0.725 (2)	0.081 (4)	0.4514 (19)	0.057*
C32	0.7068 (3)	−0.0168 (4)	0.35925 (19)	0.0330 (11)
C33	0.6370 (3)	−0.1301 (4)	0.3741 (2)	0.0393 (12)
H33A	0.6514	−0.2050	0.3351	0.047*
H33B	0.6454	−0.1645	0.4317	0.047*
N34	0.5380 (2)	−0.0898 (3)	0.36282 (15)	0.0321 (9)
C34	0.4953 (4)	−0.1566 (4)	0.2901 (3)	0.0593 (13)
H34A	0.5305	−0.1322	0.2395	0.089*
H34B	0.4294	−0.1275	0.2843	0.089*
H34C	0.4975	−0.2548	0.2978	0.089*
C35	0.4787 (3)	−0.0994 (4)	0.4377 (2)	0.0409 (12)
H35A	0.5167	−0.1374	0.4841	0.049*
H35B	0.4258	−0.1622	0.4266	0.049*
C36	0.4393 (3)	0.0357 (5)	0.4642 (2)	0.0371 (11)
O37	0.51499 (19)	0.1230 (3)	0.48663 (15)	0.0444 (8)
H37	0.5662 (19)	0.111 (4)	0.463 (2)	0.067*
C38	0.8072 (3)	−0.0694 (4)	0.3662 (2)	0.0495 (13)
H38A	0.8515	0.0066	0.3639	0.074*
H38B	0.8201	−0.1314	0.3198	0.074*
H38C	0.8149	−0.1174	0.4194	0.074*
C39	0.6915 (3)	0.0493 (3)	0.27373 (18)	0.0543 (14)
H39A	0.7316	0.1297	0.2691	0.081*
H39B	0.6251	0.0756	0.2679	0.081*
H39C	0.7081	−0.0150	0.2295	0.081*
C40	0.3803 (3)	0.0181 (5)	0.5426 (2)	0.0577 (13)
H40A	0.4193	−0.0215	0.5869	0.087*
H40B	0.3268	−0.0417	0.5307	0.087*
H40C	0.3567	0.1064	0.5610	0.087*
C41	0.3790 (3)	0.1033 (4)	0.3960 (2)	0.0557 (13)
H41A	0.3523	0.1876	0.4177	0.084*
H41B	0.3277	0.0423	0.3795	0.084*
H41C	0.4187	0.1230	0.3473	0.084*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
O11	0.0255 (18)	0.039 (2)	0.104 (2)	0.0015 (18)	−0.0051 (17)	−0.029 (2)
C12	0.029 (2)	0.035 (3)	0.055 (2)	−0.002 (2)	0.001 (3)	−0.001 (3)
C13	0.037 (3)	0.031 (3)	0.055 (3)	−0.012 (2)	−0.011 (2)	0.009 (2)
N14	0.034 (2)	0.043 (3)	0.045 (2)	0.002 (2)	−0.0089 (17)	−0.0028 (17)
C14	0.062 (4)	0.095 (4)	0.055 (3)	−0.004 (3)	−0.005 (3)	−0.018 (3)
C15	0.055 (3)	0.035 (3)	0.051 (2)	0.009 (3)	0.004 (2)	−0.001 (2)
C16	0.033 (3)	0.034 (3)	0.034 (2)	0.003 (2)	−0.003 (2)	0.004 (2)
O17	0.0292 (18)	0.068 (2)	0.0355 (16)	0.0103 (16)	−0.0004 (15)	−0.0111 (14)
C18	0.047 (3)	0.086 (4)	0.046 (2)	0.004 (3)	0.002 (3)	0.002 (3)
C19	0.030 (3)	0.043 (3)	0.058 (3)	−0.001 (2)	−0.006 (2)	0.012 (2)
C20	0.055 (3)	0.051 (3)	0.040 (2)	−0.001 (2)	−0.001 (2)	0.012 (2)
C21	0.038 (3)	0.070 (4)	0.050 (2)	0.021 (3)	0.008 (2)	0.008 (2)
O31	0.0303 (18)	0.0394 (17)	0.0452 (16)	0.0008 (15)	−0.0075 (13)	−0.0113 (15)
C32	0.023 (2)	0.046 (3)	0.030 (2)	0.012 (2)	0.003 (2)	−0.002 (2)
C33	0.049 (3)	0.035 (3)	0.034 (2)	−0.001 (2)	0.002 (2)	−0.0092 (19)
N34	0.030 (2)	0.032 (2)	0.034 (2)	−0.0035 (18)	−0.0050 (18)	−0.0084 (16)
C34	0.043 (3)	0.089 (4)	0.046 (2)	0.000 (3)	−0.014 (2)	−0.028 (3)
C35	0.047 (3)	0.038 (3)	0.037 (3)	−0.005 (2)	−0.006 (2)	0.001 (2)
C36	0.029 (3)	0.040 (3)	0.041 (2)	−0.003 (2)	0.006 (2)	−0.003 (2)
O37	0.0283 (19)	0.043 (2)	0.0613 (18)	−0.0015 (17)	0.0105 (14)	−0.0197 (15)
C38	0.035 (3)	0.066 (4)	0.047 (2)	0.013 (3)	−0.004 (2)	−0.013 (2)
C39	0.050 (3)	0.072 (4)	0.041 (2)	0.011 (3)	0.008 (2)	0.023 (2)
C40	0.040 (3)	0.083 (4)	0.050 (2)	−0.007 (3)	0.014 (3)	0.001 (3)
C41	0.044 (3)	0.065 (3)	0.058 (3)	0.013 (3)	−0.006 (2)	0.006 (3)

Geometric parameters (Å, º) top

O11—C12	1.430 (5)	O31—C32	1.431 (4)
O11—H11	0.76 (2)	O31—H31	0.74 (2)
C12—C19	1.499 (5)	C32—C33	1.513 (5)
C12—C13	1.525 (5)	C32—C38	1.518 (5)
C12—C18	1.535 (5)	C32—C39	1.532 (4)
C13—N14	1.446 (4)	C33—N34	1.468 (5)
C13—H13A	0.9900	C33—H33A	0.9900
C13—H13B	0.9900	C33—H33B	0.9900
N14—C14	1.459 (4)	N34—C35	1.465 (4)
N14—C15	1.465 (4)	N34—C34	1.468 (4)
C14—H14A	0.9800	C34—H34A	0.9800
C14—H14B	0.9800	C34—H34B	0.9800
C14—H14C	0.9800	C34—H34C	0.9800
C15—C16	1.517 (5)	C35—C36	1.510 (5)
C15—H15A	0.9900	C35—H35A	0.9900
C15—H15B	0.9900	C35—H35B	0.9900
C16—O17	1.449 (4)	C36—O37	1.423 (5)
C16—C20	1.506 (4)	C36—C40	1.516 (5)
C16—C21	1.505 (5)	C36—C41	1.539 (5)
O17—H17	0.80 (2)	O37—H37	0.83 (2)
C18—H18A	0.9800	C38—H38A	0.9800
C18—H18B	0.9800	C38—H38B	0.9800
C18—H18C	0.9800	C38—H38C	0.9800
C19—H19A	0.9800	C39—H39A	0.9800
C19—H19B	0.9800	C39—H39B	0.9800
C19—H19C	0.9800	C39—H39C	0.9800
C20—H20A	0.9800	C40—H40A	0.9800
C20—H20B	0.9800	C40—H40B	0.9800
C20—H20C	0.9800	C40—H40C	0.9800
C21—H21A	0.9800	C41—H41A	0.9800
C21—H21B	0.9800	C41—H41B	0.9800
C21—H21C	0.9800	C41—H41C	0.9800

C12—O11—H11	118 (4)	C32—O31—H31	106 (3)
O11—C12—C19	110.2 (4)	O31—C32—C33	108.7 (3)
O11—C12—C13	104.8 (3)	O31—C32—C38	111.4 (3)
C19—C12—C13	113.5 (4)	C33—C32—C38	110.2 (4)
O11—C12—C18	109.0 (4)	O31—C32—C39	104.8 (3)
C19—C12—C18	110.4 (3)	C33—C32—C39	111.4 (3)
C13—C12—C18	108.8 (3)	C38—C32—C39	110.1 (3)
N14—C13—C12	114.5 (3)	N34—C33—C32	113.7 (3)
N14—C13—H13A	108.6	N34—C33—H33A	108.8
C12—C13—H13A	108.6	C32—C33—H33A	108.8
N14—C13—H13B	108.6	N34—C33—H33B	108.8
C12—C13—H13B	108.6	C32—C33—H33B	108.8
H13A—C13—H13B	107.6	H33A—C33—H33B	107.7
C13—N14—C14	110.8 (4)	C33—N34—C35	115.4 (3)
C13—N14—C15	115.3 (3)	C33—N34—C34	111.6 (3)
C14—N14—C15	112.4 (3)	C35—N34—C34	112.5 (3)
N14—C14—H14A	109.5	N34—C34—H34A	109.5
N14—C14—H14B	109.5	N34—C34—H34B	109.5
H14A—C14—H14B	109.5	H34A—C34—H34B	109.5
N14—C14—H14C	109.5	N34—C34—H34C	109.5
H14A—C14—H14C	109.5	H34A—C34—H34C	109.5
H14B—C14—H14C	109.5	H34B—C34—H34C	109.5
N14—C15—C16	115.5 (4)	N34—C35—C36	112.6 (3)
N14—C15—H15A	108.4	N34—C35—H35A	109.1
C16—C15—H15A	108.4	C36—C35—H35A	109.1
N14—C15—H15B	108.4	N34—C35—H35B	109.1
C16—C15—H15B	108.4	C36—C35—H35B	109.1
H15A—C15—H15B	107.5	H35A—C35—H35B	107.8
O17—C16—C20	108.4 (3)	O37—C36—C35	109.3 (3)
O17—C16—C21	105.9 (3)	O37—C36—C40	106.0 (3)
C20—C16—C21	112.6 (3)	C35—C36—C40	109.6 (4)
O17—C16—C15	109.3 (3)	O37—C36—C41	109.4 (3)
C20—C16—C15	110.3 (3)	C35—C36—C41	113.0 (3)
C21—C16—C15	110.1 (4)	C40—C36—C41	109.4 (4)
C16—O17—H17	112 (3)	C36—O37—H37	117 (3)
C12—C18—H18A	109.5	C32—C38—H38A	109.5
C12—C18—H18B	109.5	C32—C38—H38B	109.5
H18A—C18—H18B	109.5	H38A—C38—H38B	109.5
C12—C18—H18C	109.5	C32—C38—H38C	109.5
H18A—C18—H18C	109.5	H38A—C38—H38C	109.5
H18B—C18—H18C	109.5	H38B—C38—H38C	109.5
C12—C19—H19A	109.5	C32—C39—H39A	109.5
C12—C19—H19B	109.5	C32—C39—H39B	109.5
H19A—C19—H19B	109.5	H39A—C39—H39B	109.5
C12—C19—H19C	109.5	C32—C39—H39C	109.5
H19A—C19—H19C	109.5	H39A—C39—H39C	109.5
H19B—C19—H19C	109.5	H39B—C39—H39C	109.5
C16—C20—H20A	109.5	C36—C40—H40A	109.5
C16—C20—H20B	109.5	C36—C40—H40B	109.5
H20A—C20—H20B	109.5	H40A—C40—H40B	109.5
C16—C20—H20C	109.5	C36—C40—H40C	109.5
H20A—C20—H20C	109.5	H40A—C40—H40C	109.5
H20B—C20—H20C	109.5	H40B—C40—H40C	109.5
C16—C21—H21A	109.5	C36—C41—H41A	109.5
C16—C21—H21B	109.5	C36—C41—H41B	109.5
H21A—C21—H21B	109.5	H41A—C41—H41B	109.5
C16—C21—H21C	109.5	C36—C41—H41C	109.5
H21A—C21—H21C	109.5	H41A—C41—H41C	109.5
H21B—C21—H21C	109.5	H41B—C41—H41C	109.5

O11—C12—C13—N14	65.9 (4)	O31—C32—C33—N34	61.5 (4)
C19—C12—C13—N14	−54.4 (5)	C38—C32—C33—N34	−176.0 (3)
C18—C12—C13—N14	−177.7 (3)	C39—C32—C33—N34	−53.5 (4)
C12—C13—N14—C14	105.6 (4)	C32—C33—N34—C35	−117.1 (4)
C12—C13—N14—C15	−125.2 (4)	C32—C33—N34—C34	112.8 (4)
C13—N14—C15—C16	94.1 (4)	C33—N34—C35—C36	118.2 (4)
C14—N14—C15—C16	−137.5 (3)	C34—N34—C35—C36	−112.2 (4)
N14—C15—C16—O17	−62.5 (4)	N34—C35—C36—O37	−63.3 (4)
N14—C15—C16—C20	56.6 (4)	N34—C35—C36—C40	−179.0 (3)
N14—C15—C16—C21	−178.5 (3)	N34—C35—C36—C41	58.7 (4)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O11—H11···O37	0.76 (2)	1.91 (2)	2.656 (3)	168 (5)
O17—H17···O11	0.80 (2)	1.84 (2)	2.621 (4)	165 (4)
O31—H31···O17ⁱ	0.74 (2)	1.99 (2)	2.712 (3)	165 (4)
O37—H37···O31	0.83 (2)	1.89 (2)	2.715 (4)	174 (4)

Symmetry code: (i) x+1/2, −y+1/2, z.

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