Crystal packing in the structures of diethanol­amine derivatives

Four distinct hydrogen-bonding topologies were observed in the structures of six diethanol­amine ligands. These compounds are (1R*,2R*)-2-[(2-hydroxy­ethyl)(methyl)amino]-1,2-diphenyl­ethanol, C₁₇H₂₁NO₂, (I), 1-[(2S)-2-(hydr­oxy­diphenyl­methyl)­pyrrolidin-1-yl]-2-methyl­propan-2-ol, C₂₁H₂₇NO₂, (II), 2-[(2-hydroxy­ethyl)(methyl)amino]-1,1-diphenyl­ethanol, C₁₇H₂₁NO₂, (III), 1-{(2-hydr­oxy-2-methyl­propyl)[(1S)-1-phenyl­ethyl]­amino}-2-methyl­propan-2-ol, C₁₆H₂₇NO₂, (IV), 1-{[(2R)-2-hydroxy-2-phenyl­ethyl][(1S)-1-phenyl­ethyl]amino}-2-methyl­propan-2-ol, C₂₀H₂₇NO₂, (V), and (1R*,2S*)-2-[(2-hydroxy­ethyl)­(methyl)­amino]-1,2-diphenyl­ethanol, C₁₇H₂₁NO₂, (VI). In each compound, all `active' hydroxy H atoms are engaged in hydrogen bonding, but the N atoms are not involved in inter­molecular hydrogen bonding. In the structures of (I), (II) and (IV)–(VI), mol­ecules are linked into chains by inter­molecular O—H...O inter­actions. These chains are organized in such a way as to hide the hydro­philic groups inside, and so the outer surfaces of the chains are hydro­phobic. The structure of (VI) contains two distinct non-equivalent systems of inter­molecular O—H...O hydrogen bonds formed by disordered hydroxy H atoms.

S1. Comment

In the last two decades, polydentate ligand frameworks have been widely used in the synthesis of transition metal complexes which may be applied as catalysts for fine organic reactions or polymerization processes (Odom, 2005; Mountford, 1998; Coates, 2002). Within this field, ligands featuring anionic O donors (alkoxides, aryloxides), and especially alkoxides with an additional intramolecular donor group, have attracted particular attention (Mack & Eisen, 1998; Chmura et al., 2006; Knight et al., 2004). Among these ligands, diethanolamines look highly intriguing, due to the relative ease of manipulating the ligand topology (cyclic or open-chain), steric hindrance, chirality and coordination ability. We reported recently the synthesis of several titanium complexes based on chiral diethanolamines (Zaitsev et al., 2008).

N-Aryldiethanolamines are well known (El-Sayed et al., 2001; Centore & Tuzi, 2003; Luger & Roch, 1983; Chen & Shi, 2006), but in their structures the N atom never normally participates in hydrogen bonding due to significant aryl–N conjugation. Additionally, the structures of N-diethanolamines where the N atom bonds to a Csp³ atom are rare (Skinner et al., 2005; Wu & Rehder, 2005). Here, we report the structures of six N-alkyldiethanolamines, (I)–(VI). In the molecules of (I)–(VI), all bond lengths have normal values and the N atoms adopt pyramidal conformations, with the sums of the bond angles in the range 334.7–341.3°. However, analysis of the hydrogen bonding in these compounds demonstrates four distinct topologies.

In structures (I) and (II), the N atom forms a bent intramolecular hydrogen bond with one of the O^a atoms (A in Scheme 1; Fig. 1, Tables 1 and 2). The O^a—H···N angle varies from 126 (2) to 131 (2)°. The resulting five-membered rings are non-planar, and both `envelope' and `twist' conformations are observed. Atom O^a accepts an intermolecular hydrogen bond from a hydroxyl group O^b—H of an adjacent molecule. Atom O^b, however, serves only as a hydrogen-bond donor for the neighbouring molecule. This motif results in the formation of chains (Fig. 2).

As in the structures of (I) and (II), in compound (III) the N atom forms an intramolecular hydrogen bond with one of the O^a atoms, with an O^a—H···N angle of 126 (2)° (Table 2). However, in contrast with (I) and (II), the molecules of (III) form centrosymmetric S(5)R₄⁴(14) dimers (Bernstein et al., 1995) (Fig. 3).

In structures (IV) and (V), the N atom does not participate in hydrogen bonding (B in Scheme 1; Fig. 4). This is probably caused by the steric requirements of the bulky CH(Me)Ph substituent bound to the amine N atoms. The O atoms form an intramolecular O^a—H···O^b hydrogen bond, resulting in an eight-membered cycle closure. Additionally, both O atoms are engaged in intermolecular hydrogen bonds, combining adjacent molecules into chains (Fig. 5). The O^a—H···O^b bond is close to linear. The identical structural motif to that in (IV) was found previously for the related diethanolamine derivative o-(C₅NH₄)CH₂N(CH₂CMe₂OH)₂ (Skinner et al., 2005) and for some aryl-substituted ligands (Seo et al., 2007).

In the structure of (VI), the N atom is not involved in hydrogen bonding and no intramolecular hydrogen bonds were observed. However, both O atoms form intermolecular hydrogen bonds, resulting in chain generation. Interestingly, both hydroxyl H atoms are disordered over two positions with approximately equal occupancies (Fig. 6). Thus, (VI) demonstrates two distinct non-equivalent systems of intermolecular O—H···O bonds (see Scheme 2; Fig. 7). We have previously observed the same type of chains in the structure of 2-(hydroxymethyl)-6-(1,7,7-trimethylbicyclo[2.2.1]hept-2-yl)phenol (Chukicheva et al., 2006). We made two data collections from the same crystal at different temperatures (100 and 300 K), but found only minimal structural changes.

In the structures of (I), (II) and (IV)–(VI), the chains are organized in such a way as to hide the hydrophilic groups inside, and hence the outer surfaces of the chains are hydrophobic. These chains are combined in two- or three-dimensional networks by T-shaped aromatic C—H···π interactions. No face-to-face intermolecular π=-π interactions were found. In the structure of (III), the dimers are also connected by intermolecular C—H···π interactions.

In all four packing motifs, we observed that the N atoms are not involved in intermolecular hydrogen bonding. However, Wu & Rehder (2005) found another supramolecular aggregation for the structure of allyldiethanolamine, (VII), where the N atom does interact intermolecularly with the hydroxyl groups. In (VII), one of two OH groups serves as both donor and acceptor of hydrogen bonds, while another acts as donor only. The latter results in the formation of hydrophobic chains of the molecules (see Scheme 3).

It is noteworthy that three of the compounds investigated here [(II), (IV) and (V)] were obtained from enantiopure amines (Zaitsev et al., 2008) and crystallize in the Sohncke space group P2₁2₁2₁, forming helical chains along 2₁ screw axes. Therefore, they possess the potential for the effective transfer of chirality to a metal centre which is essential for successful asymmetric metal-based catalysis.

S2. Experimental

Compounds (I)–(VI) were synthesized by the methods described by Zaitsev et al. (2008). Single colourless crystals suitable for X-ray diffraction analysis were obtained from toluene solutions upon freezing to 258 K.

S3. Refinement

In the structures of (I) and (III)–(V), the hydroxyl H atoms were found in difference Fourier syntheses and refined with isotropic displacement parameters. In (II), all H atoms were found in a difference Fourier synthesis and refined isotropically. In (VI), the disordered hydroxyl H atoms were also found in a difference Fourier synthesis and refined with U_iso(H) = 1.5U_eq(O). The occupancies of these hydroxyl H atoms were refined in the last runs of SHELXL97 (Sheldrick, 2008). Their values converged to 0.51 (2):0.49 (2) for both datasets collected at 100 and 300 K from the same crystal. In all compounds, all other (C-bound) H atoms were placed in calculated positions and refined using a riding model, with C—H = 0.95 (aromatic), 0.98 (CH₃), 0.99 (CH₂) or 1.00 Å (CH), and with U_iso(H) = kU_eq(carrier), where k = 1.5 for the methyl groups, which were permitted to rotate but not to tilt, and k = 1.2 for all other H atoms. In the noncentrosymmetric structures (I), (II), (IV) and (V), Friedel pairs were merged in the final refinements (MERG 3 instruction in SHELXL97). In (VI), the possibility of a superstructure was checked but was not confirmed.

Computing details

For all compounds, data collection: SMART (Bruker, 2004); cell refinement: SAINT (Bruker, 2004); data reduction: SAINT (Bruker, 2004); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXTL (Sheldrick, 2008).

Figures

	Fig. 1. The molecular structures of (a) (I) and (b) (II), showing the atom-numbering schemes. Displacement ellipsoids are drawn at the 50% probability level and hydroxyl H atoms are shown as small spheres of arbitrary radii. Hydrogen bonds are shown as dashed lines. H atoms bonded to C atoms have been omitted for clarity.
	Fig. 2. Chains along the b axis in the structure of (II). Hydrogen bonds are shown as dashed lines. H atoms not involved in hydrogen bonding have been omitted for clarity. [Symmetry codes: (i) 1 - x, -1/2 + y, 1/2 - z; (ii) x, -1 + y, z; (iii) 1 - x, -3/2 + y, 1/2 - z.]
	Fig. 3. The centrosymmetric dimer in the structure of (III), showing the atom-numbering scheme [Please complete numbering]. Displacement ellipsoids are drawn at the 50% probability level and hydroxyl H atoms are shown as small spheres of arbitrary radii. Hydrogen bonds are shown as dashed lines. H atoms not involved in hydrogen bonding have been omitted for clarity. [Symmetry codes: (i) 2 - x, -y, 1 - z.]
	Fig. 4. The molecular structures of (a) (IV) and (b) (V), showing the atom-numbering schemes. Displacement ellipsoids are drawn at the 50% probability level and hydroxyl H atoms are shown as small spheres of arbitrary radii. The intramolecular hydrogen bond is shown as a dashed line. H atoms bonded to C atoms have been omitted for clarity.
	Fig. 5. Chains along the a axis in the structures of (a) (IV) and (b) (V). Hydrogen bonds are shown as dashed lines. H atoms not involved in hydrogen bonding have been omitted for clarity. [Symmetry codes for (a): (i) 1/2 + x, -1/2 - y, -z; (ii) 1 + x, y, z; (iii) -1/2 + x, -1/2 - y, -z. Symmetry codes for (b): (i) -1/2 + x, 3/2 - y, -z; (ii) -1 + x, y, z; (iii) 1/2 + x, 3/2 - y, -z.]
	Fig. 6. The molecular structure of (VI), showing the atom-numbering scheme. Displacement ellipsoids are drawn at the 50% probability level and hydroxyl H atoms are shown as small spheres of arbitrary radii. H atoms bonded to C atoms have been omitted for clarity.
	Fig. 7. The disordered double chains in the structure of (VI). Hydrogen bonds are shown as dashed lines. H atoms not involved in hydrogen bonding have been omitted for clarity. [Symmetry codes: (i) 1 + x, y, z; (ii) -1 + x, y, z; (iii) 1 - x, 1 - y, 1 - z; (iv) -x, 1 - y, 1 - z; (v) -1 - x, 1 - y, 1 - z.]

(I) 2-[(2-hydroxyethyl)(methyl)amino]-1,2-diphenylethanol

Crystal data

C17H21NO2	F(000) = 292
Mr = 271.35	Dx = 1.245 Mg m^−3
Monoclinic, Pc	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P -2yc	Cell parameters from 4308 reflections
a = 5.8366 (1) Å	θ = 2.5–29.9°
b = 15.3018 (4) Å	µ = 0.08 mm^−1
c = 8.1078 (2) Å	T = 120 K
β = 91.444 (1)°	Block, colourless
V = 723.88 (3) Å^3	0.40 × 0.20 × 0.10 mm
Z = 2

Data collection

Bruker SMART 1K diffractometer	1677 independent reflections
Radiation source: fine-focus sealed tube	1626 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.029
ω scans	θmax = 27.5°, θmin = 2.7°
Absorption correction: multi-scan (SADABS; Bruker, 2004)	h = −7→7
Tmin = 0.968, Tmax = 0.992	k = −19→19
4958 measured reflections	l = −10→10

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)] = 0.030	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.077	H atoms treated by a mixture of independent and constrained refinement
S = 1.06	w = 1/[σ^2(Fo^2) + (0.0487P)^2 + 0.0768P] where P = (Fo^2 + 2Fc^2)/3
1677 reflections	(Δ/σ)max < 0.001
190 parameters	Δρmax = 0.26 e Å^−3
2 restraints	Δρmin = −0.19 e Å^−3

Special details

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 (Ų)

	x	y	z	Uiso*/Ueq
N1	0.8651 (2)	0.35398 (9)	0.27939 (17)	0.0166 (3)
O1	0.6689 (2)	0.52412 (8)	0.25285 (17)	0.0253 (3)
O2	0.9803 (2)	0.40890 (8)	−0.01196 (15)	0.0206 (3)
C1	0.5441 (3)	0.45589 (11)	0.3303 (2)	0.0214 (3)
H1A	0.3781	0.4644	0.3078	0.026*
H1B	0.5714	0.4588	0.4512	0.026*
C2	0.6157 (3)	0.36586 (11)	0.2676 (2)	0.0188 (3)
H2A	0.5404	0.3200	0.3332	0.023*
H2B	0.5635	0.3591	0.1511	0.023*
C3	0.9522 (3)	0.34606 (12)	0.4504 (2)	0.0212 (3)
H3A	0.9002	0.3962	0.5147	0.032*
H3B	1.1201	0.3448	0.4516	0.032*
H3C	0.8944	0.2919	0.4988	0.032*
C4	0.9550 (3)	0.28428 (10)	0.17160 (19)	0.0151 (3)
H4	1.1226	0.2792	0.1986	0.018*
C5	0.9338 (3)	0.31695 (10)	−0.0104 (2)	0.0163 (3)
H5	0.7735	0.3069	−0.0525	0.020*
C11	0.8504 (3)	0.19411 (10)	0.2025 (2)	0.0163 (3)
C6	0.9644 (3)	0.13769 (11)	0.3123 (2)	0.0209 (3)
H6	1.1094	0.1541	0.3582	0.025*
C7	0.8684 (3)	0.05745 (12)	0.3557 (2)	0.0265 (4)
H7	0.9476	0.0200	0.4313	0.032*
C8	0.6575 (4)	0.03254 (12)	0.2885 (2)	0.0266 (4)
H8	0.5920	−0.0220	0.3176	0.032*
C9	0.5422 (3)	0.08783 (12)	0.1780 (2)	0.0236 (4)
H9	0.3981	0.0707	0.1314	0.028*
C10	0.6368 (3)	0.16814 (11)	0.1354 (2)	0.0190 (3)
H10	0.5563	0.2055	0.0605	0.023*
C12	1.0991 (3)	0.27011 (11)	−0.12307 (19)	0.0161 (3)
C13	1.0579 (3)	0.18331 (11)	−0.1715 (2)	0.0205 (3)
H13	0.9265	0.1535	−0.1337	0.025*
C14	1.2093 (3)	0.14079 (12)	−0.2747 (2)	0.0243 (4)
H14	1.1815	0.0818	−0.3055	0.029*
C15	1.4011 (3)	0.18402 (13)	−0.3333 (2)	0.0243 (4)
H15	1.5042	0.1548	−0.4034	0.029*
C16	1.4396 (3)	0.27083 (12)	−0.2876 (2)	0.0217 (4)
H16	1.5683	0.3012	−0.3285	0.026*
C17	1.2906 (3)	0.31327 (11)	−0.1823 (2)	0.0185 (3)
H17	1.3198	0.3721	−0.1508	0.022*
H1	0.770 (5)	0.5387 (16)	0.321 (4)	0.035 (7)*
H2	0.948 (5)	0.4278 (18)	0.081 (4)	0.042 (7)*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
N1	0.0161 (6)	0.0189 (7)	0.0149 (7)	0.0006 (5)	0.0014 (5)	−0.0018 (5)
O1	0.0322 (7)	0.0203 (6)	0.0231 (6)	−0.0007 (5)	−0.0033 (6)	0.0022 (5)
O2	0.0283 (6)	0.0155 (6)	0.0183 (6)	0.0005 (5)	0.0050 (5)	0.0013 (5)
C1	0.0220 (8)	0.0200 (8)	0.0223 (8)	0.0020 (7)	0.0023 (7)	−0.0022 (7)
C2	0.0160 (7)	0.0201 (8)	0.0202 (8)	−0.0001 (6)	0.0015 (6)	−0.0018 (6)
C3	0.0209 (8)	0.0266 (9)	0.0160 (8)	0.0010 (7)	−0.0003 (6)	−0.0012 (6)
C4	0.0140 (6)	0.0163 (7)	0.0151 (7)	0.0007 (6)	0.0016 (6)	0.0002 (6)
C5	0.0163 (7)	0.0158 (7)	0.0167 (7)	0.0008 (6)	0.0017 (6)	0.0014 (6)
C11	0.0190 (8)	0.0154 (7)	0.0145 (7)	0.0011 (6)	0.0039 (6)	−0.0002 (6)
C6	0.0225 (8)	0.0193 (8)	0.0208 (8)	0.0019 (6)	−0.0007 (7)	−0.0003 (6)
C7	0.0377 (10)	0.0189 (8)	0.0228 (9)	0.0027 (8)	0.0001 (8)	0.0037 (7)
C8	0.0371 (10)	0.0181 (8)	0.0247 (9)	−0.0059 (7)	0.0057 (8)	−0.0009 (7)
C9	0.0241 (8)	0.0240 (9)	0.0228 (8)	−0.0058 (7)	0.0037 (7)	−0.0039 (7)
C10	0.0185 (7)	0.0199 (8)	0.0189 (8)	0.0006 (6)	0.0018 (6)	−0.0002 (6)
C12	0.0177 (7)	0.0186 (8)	0.0120 (7)	0.0014 (6)	−0.0001 (6)	0.0009 (6)
C13	0.0226 (8)	0.0198 (8)	0.0193 (8)	−0.0012 (7)	0.0022 (7)	0.0002 (6)
C14	0.0294 (10)	0.0218 (8)	0.0216 (9)	0.0037 (7)	0.0005 (7)	−0.0039 (7)
C15	0.0240 (8)	0.0319 (10)	0.0170 (8)	0.0078 (7)	0.0018 (7)	−0.0009 (7)
C16	0.0175 (8)	0.0316 (9)	0.0162 (8)	−0.0001 (7)	0.0022 (6)	0.0023 (7)
C17	0.0194 (7)	0.0214 (8)	0.0147 (8)	−0.0015 (6)	−0.0002 (6)	0.0014 (6)

Geometric parameters (Å, º)

N1—C2	1.468 (2)	C11—C10	1.405 (2)
N1—C3	1.469 (2)	C6—C7	1.398 (3)
N1—C4	1.483 (2)	C6—H6	0.9500
O1—C1	1.427 (2)	C7—C8	1.387 (3)
O1—H1	0.83 (3)	C7—H7	0.9500
O2—C5	1.4329 (19)	C8—C9	1.393 (3)
O2—H2	0.83 (3)	C8—H8	0.9500
C1—C2	1.530 (2)	C9—C10	1.394 (2)
C1—H1A	0.9900	C9—H9	0.9500
C1—H1B	0.9900	C10—H10	0.9500
C2—H2A	0.9900	C12—C17	1.394 (2)
C2—H2B	0.9900	C12—C13	1.404 (2)
C3—H3A	0.9800	C13—C14	1.394 (2)
C3—H3B	0.9800	C13—H13	0.9500
C3—H3C	0.9800	C14—C15	1.394 (3)
C4—C11	1.532 (2)	C14—H14	0.9500
C4—C5	1.560 (2)	C15—C16	1.396 (3)
C4—H4	1.0000	C15—H15	0.9500
C5—C12	1.524 (2)	C16—C17	1.394 (2)
C5—H5	1.0000	C16—H16	0.9500
C11—C6	1.397 (2)	C17—H17	0.9500
C2—N1—C3	113.00 (13)	C6—C11—C4	118.40 (15)
C2—N1—C4	114.56 (13)	C10—C11—C4	123.01 (14)
C3—N1—C4	112.18 (13)	C7—C6—C11	121.06 (17)
C1—O1—H1	105.5 (19)	C7—C6—H6	119.5
C5—O2—H2	106.7 (19)	C11—C6—H6	119.5
O1—C1—C2	111.44 (14)	C8—C7—C6	119.97 (17)
O1—C1—H1A	109.3	C8—C7—H7	120.0
C2—C1—H1A	109.3	C6—C7—H7	120.0
O1—C1—H1B	109.3	C7—C8—C9	119.70 (17)
C2—C1—H1B	109.3	C7—C8—H8	120.2
H1A—C1—H1B	108.0	C9—C8—H8	120.2
N1—C2—C1	111.62 (14)	C10—C9—C8	120.44 (17)
N1—C2—H2A	109.3	C10—C9—H9	119.8
C1—C2—H2A	109.3	C8—C9—H9	119.8
N1—C2—H2B	109.3	C9—C10—C11	120.41 (16)
C1—C2—H2B	109.3	C9—C10—H10	119.8
H2A—C2—H2B	108.0	C11—C10—H10	119.8
N1—C3—H3A	109.5	C17—C12—C13	119.00 (15)
N1—C3—H3B	109.5	C17—C12—C5	120.59 (14)
H3A—C3—H3B	109.5	C13—C12—C5	120.40 (14)
N1—C3—H3C	109.5	C14—C13—C12	120.20 (16)
H3A—C3—H3C	109.5	C14—C13—H13	119.9
H3B—C3—H3C	109.5	C12—C13—H13	119.9
N1—C4—C11	113.74 (13)	C15—C14—C13	120.65 (16)
N1—C4—C5	107.83 (12)	C15—C14—H14	119.7
C11—C4—C5	114.90 (13)	C13—C14—H14	119.7
N1—C4—H4	106.6	C14—C15—C16	119.12 (16)
C11—C4—H4	106.6	C14—C15—H15	120.4
C5—C4—H4	106.6	C16—C15—H15	120.4
O2—C5—C12	109.50 (13)	C15—C16—C17	120.45 (16)
O2—C5—C4	108.20 (13)	C15—C16—H16	119.8
C12—C5—C4	112.32 (13)	C17—C16—H16	119.8
O2—C5—H5	108.9	C12—C17—C16	120.56 (15)
C12—C5—H5	108.9	C12—C17—H17	119.7
C4—C5—H5	108.9	C16—C17—H17	119.7
C6—C11—C10	118.42 (15)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
O1—H1···O2^i	0.83 (3)	1.97 (3)	2.7954 (19)	170 (3)
O2—H2···N1	0.83 (3)	2.04 (3)	2.6111 (18)	126 (2)

Symmetry code: (i) x, −y+1, z+1/2.

(II) 1-{2-[hydroxy(diphenyl)methyl]pyrrolidin-1-yl}- 2-methylpropan-2-ol

Crystal data

C21H27NO2	F(000) = 704
Mr = 325.44	Dx = 1.206 Mg m^−3
Orthorhombic, P212121	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2ac 2ab	Cell parameters from 6375 reflections
a = 8.5024 (4) Å	θ = 2.3–29.9°
b = 11.9480 (5) Å	µ = 0.08 mm^−1
c = 17.6485 (7) Å	T = 120 K
V = 1792.85 (13) Å^3	Block, colourless
Z = 4	0.30 × 0.24 × 0.20 mm

Data collection

Bruker SMART 1K diffractometer	2712 independent reflections
Radiation source: fine-focus sealed tube	2398 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.040
ω scans	θmax = 29.0°, θmin = 2.1°
Absorption correction: multi-scan (SADABS; Bruker, 2004)	h = −11→11
Tmin = 0.977, Tmax = 0.985	k = −12→16
12996 measured reflections	l = −19→24

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)] = 0.035	Hydrogen site location: difference Fourier map
wR(F^2) = 0.083	All H-atom parameters refined
S = 1.03	w = 1/[σ^2(Fo^2) + (0.0452P)^2 + 0.2289P] where P = (Fo^2 + 2Fc^2)/3
2712 reflections	(Δ/σ)max < 0.001
325 parameters	Δρmax = 0.21 e Å^−3
0 restraints	Δρmin = −0.20 e Å^−3

Special details

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 (Ų)

	x	y	z	Uiso*/Ueq
N1	0.35346 (16)	0.52971 (12)	0.27771 (8)	0.0168 (3)
O1	0.28678 (14)	0.74120 (10)	0.30108 (7)	0.0189 (2)
O2	0.66413 (14)	0.47597 (11)	0.20799 (7)	0.0221 (3)
C1	0.5350 (2)	0.52078 (14)	0.16482 (9)	0.0189 (3)
C2	0.37558 (19)	0.48853 (14)	0.19995 (10)	0.0184 (3)
C3	0.5592 (2)	0.64710 (15)	0.16528 (11)	0.0225 (4)
C4	0.5423 (2)	0.47535 (18)	0.08388 (10)	0.0263 (4)
C5	0.4226 (2)	0.45467 (15)	0.33634 (10)	0.0227 (4)
C6	0.2884 (3)	0.42443 (16)	0.38944 (11)	0.0280 (4)
C7	0.1827 (2)	0.52712 (16)	0.38402 (10)	0.0232 (4)
C8	0.18740 (19)	0.55350 (13)	0.29899 (9)	0.0167 (3)
C9	0.14822 (18)	0.67934 (13)	0.28141 (9)	0.0167 (3)
C10	0.10664 (18)	0.70077 (14)	0.19757 (9)	0.0180 (3)
C11	0.1615 (2)	0.79812 (15)	0.16237 (10)	0.0228 (4)
C12	0.1260 (2)	0.82006 (18)	0.08651 (11)	0.0306 (4)
C13	0.0340 (2)	0.7466 (2)	0.04558 (10)	0.0314 (4)
C14	−0.0230 (2)	0.65083 (18)	0.08018 (10)	0.0279 (4)
C15	0.0126 (2)	0.62770 (16)	0.15586 (10)	0.0224 (4)
C16	0.01362 (19)	0.71839 (13)	0.33306 (9)	0.0172 (3)
C17	0.0390 (2)	0.79870 (15)	0.38896 (10)	0.0218 (3)
C18	−0.0794 (2)	0.82608 (17)	0.44028 (10)	0.0260 (4)
C19	−0.2242 (2)	0.77320 (16)	0.43673 (10)	0.0247 (4)
C20	−0.2520 (2)	0.69529 (17)	0.37973 (10)	0.0251 (4)
C21	−0.1349 (2)	0.66812 (15)	0.32815 (10)	0.0226 (4)
H1	0.360 (3)	0.695 (2)	0.2932 (14)	0.037 (7)*
H2	0.673 (3)	0.406 (2)	0.2018 (15)	0.039 (7)*
H8	0.111 (2)	0.5054 (17)	0.2722 (10)	0.016 (5)*
H11	0.226 (3)	0.8489 (19)	0.1884 (13)	0.029 (6)*
H12	0.166 (2)	0.8904 (19)	0.0638 (12)	0.024 (5)*
H13	0.004 (3)	0.759 (2)	−0.0051 (15)	0.040 (6)*
H14	−0.094 (3)	0.5981 (19)	0.0528 (11)	0.026 (5)*
H15	−0.030 (2)	0.5631 (18)	0.1773 (11)	0.021 (5)*
H17	0.141 (2)	0.8358 (17)	0.3923 (11)	0.019 (5)*
H18	−0.063 (3)	0.881 (2)	0.4783 (12)	0.030 (6)*
H19	−0.306 (3)	0.7904 (18)	0.4737 (12)	0.026 (5)*
H20	−0.358 (3)	0.6615 (19)	0.3750 (12)	0.027 (6)*
H21	−0.158 (2)	0.6126 (17)	0.2876 (11)	0.015 (5)*
H22	0.294 (2)	0.5219 (18)	0.1672 (11)	0.023 (5)*
H23	0.368 (2)	0.4065 (18)	0.1989 (12)	0.022 (5)*
H31	0.650 (3)	0.6659 (19)	0.1338 (12)	0.027 (6)*
H32	0.467 (3)	0.6827 (18)	0.1449 (12)	0.024 (5)*
H33	0.573 (2)	0.6771 (18)	0.2192 (12)	0.023 (5)*
H41	0.535 (3)	0.393 (2)	0.0857 (12)	0.031 (6)*
H42	0.451 (3)	0.507 (2)	0.0521 (13)	0.040 (7)*
H43	0.642 (3)	0.4923 (19)	0.0583 (13)	0.028 (6)*
H51	0.506 (3)	0.494 (2)	0.3651 (12)	0.032 (6)*
H52	0.473 (3)	0.3898 (19)	0.3115 (12)	0.027 (5)*
H61	0.327 (3)	0.409 (2)	0.4391 (14)	0.033 (6)*
H62	0.231 (3)	0.358 (2)	0.3697 (12)	0.027 (6)*
H71	0.077 (3)	0.513 (2)	0.4013 (13)	0.034 (6)*
H72	0.229 (3)	0.589 (2)	0.4111 (13)	0.033 (6)*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
N1	0.0180 (6)	0.0155 (6)	0.0168 (6)	0.0015 (5)	−0.0003 (5)	0.0015 (5)
O1	0.0165 (5)	0.0148 (5)	0.0255 (6)	−0.0015 (5)	−0.0002 (5)	−0.0021 (5)
O2	0.0193 (5)	0.0162 (6)	0.0307 (7)	0.0028 (5)	−0.0023 (5)	0.0004 (5)
C1	0.0188 (7)	0.0168 (7)	0.0210 (8)	0.0019 (7)	0.0002 (7)	0.0005 (6)
C2	0.0179 (7)	0.0183 (8)	0.0191 (8)	−0.0007 (6)	0.0009 (6)	−0.0022 (6)
C3	0.0237 (8)	0.0166 (8)	0.0273 (9)	0.0012 (7)	0.0032 (8)	0.0038 (7)
C4	0.0264 (9)	0.0294 (10)	0.0231 (9)	0.0003 (8)	0.0033 (7)	−0.0032 (7)
C5	0.0232 (8)	0.0206 (8)	0.0244 (8)	0.0017 (7)	−0.0030 (7)	0.0052 (7)
C6	0.0342 (10)	0.0235 (9)	0.0263 (9)	0.0058 (9)	0.0039 (8)	0.0096 (7)
C7	0.0301 (10)	0.0207 (8)	0.0186 (8)	0.0047 (8)	0.0035 (7)	0.0038 (7)
C8	0.0166 (7)	0.0145 (7)	0.0190 (7)	−0.0015 (6)	0.0002 (6)	0.0005 (6)
C9	0.0181 (7)	0.0136 (7)	0.0183 (7)	−0.0014 (6)	−0.0006 (6)	0.0001 (6)
C10	0.0162 (7)	0.0203 (7)	0.0176 (7)	0.0047 (6)	0.0018 (6)	0.0002 (6)
C11	0.0231 (8)	0.0216 (8)	0.0236 (9)	0.0038 (7)	0.0012 (7)	0.0039 (7)
C12	0.0335 (10)	0.0328 (10)	0.0256 (9)	0.0081 (9)	0.0084 (8)	0.0112 (8)
C13	0.0343 (10)	0.0428 (11)	0.0170 (8)	0.0154 (10)	0.0022 (8)	0.0036 (8)
C14	0.0254 (9)	0.0369 (11)	0.0216 (9)	0.0078 (8)	−0.0024 (7)	−0.0043 (7)
C15	0.0216 (8)	0.0258 (8)	0.0199 (8)	0.0018 (7)	0.0009 (7)	0.0000 (7)
C16	0.0194 (7)	0.0156 (7)	0.0167 (7)	0.0024 (6)	0.0000 (6)	0.0018 (6)
C17	0.0235 (8)	0.0202 (8)	0.0218 (8)	−0.0023 (7)	0.0008 (7)	−0.0029 (7)
C18	0.0297 (9)	0.0279 (9)	0.0203 (8)	0.0021 (8)	0.0009 (7)	−0.0061 (7)
C19	0.0251 (9)	0.0278 (9)	0.0212 (8)	0.0059 (7)	0.0045 (7)	0.0018 (7)
C20	0.0211 (8)	0.0277 (9)	0.0266 (9)	−0.0011 (8)	0.0032 (7)	0.0013 (7)
C21	0.0221 (8)	0.0235 (8)	0.0220 (9)	−0.0020 (7)	−0.0002 (7)	−0.0022 (7)

Geometric parameters (Å, º)

N1—C2	1.470 (2)	C8—C9	1.571 (2)
N1—C8	1.488 (2)	C8—H8	0.99 (2)
N1—C5	1.490 (2)	C9—C16	1.536 (2)
O1—C9	1.4334 (19)	C9—C10	1.543 (2)
O1—H1	0.84 (3)	C10—C15	1.394 (2)
O2—C1	1.439 (2)	C10—C11	1.399 (2)
O2—H2	0.85 (3)	C11—C12	1.397 (3)
C1—C3	1.523 (2)	C11—H11	0.94 (2)
C1—C4	1.530 (2)	C12—C13	1.380 (3)
C1—C2	1.540 (2)	C12—H12	0.99 (2)
C2—H22	0.98 (2)	C13—C14	1.385 (3)
C2—H23	0.98 (2)	C13—H13	0.94 (3)
C3—H31	0.98 (2)	C14—C15	1.397 (3)
C3—H32	0.96 (2)	C14—H14	1.00 (2)
C3—H33	1.02 (2)	C15—H15	0.93 (2)
C4—H41	0.99 (2)	C16—C17	1.393 (2)
C4—H42	1.03 (3)	C16—C21	1.401 (2)
C4—H43	0.99 (2)	C17—C18	1.393 (3)
C5—C6	1.520 (3)	C17—H17	0.98 (2)
C5—H51	0.99 (2)	C18—C19	1.386 (3)
C5—H52	0.99 (2)	C18—H18	0.95 (2)
C6—C7	1.524 (3)	C19—C20	1.391 (3)
C6—H61	0.96 (2)	C19—H19	0.98 (2)
C6—H62	0.99 (2)	C20—C21	1.388 (2)
C7—C8	1.534 (2)	C20—H20	0.99 (2)
C7—H71	0.96 (3)	C21—H21	0.99 (2)
C7—H72	0.96 (2)
C2—N1—C8	114.89 (13)	N1—C8—C9	109.52 (13)
C2—N1—C5	113.36 (14)	C7—C8—C9	112.60 (14)
C8—N1—C5	108.29 (13)	N1—C8—H8	113.0 (11)
C9—O1—H1	103.1 (17)	C7—C8—H8	109.4 (11)
C1—O2—H2	111.3 (17)	C9—C8—H8	108.8 (11)
O2—C1—C3	105.26 (14)	O1—C9—C16	108.19 (13)
O2—C1—C4	109.37 (14)	O1—C9—C10	109.57 (13)
C3—C1—C4	110.56 (15)	C16—C9—C10	110.37 (13)
O2—C1—C2	111.43 (13)	O1—C9—C8	105.75 (12)
C3—C1—C2	111.37 (14)	C16—C9—C8	109.37 (13)
C4—C1—C2	108.83 (14)	C10—C9—C8	113.38 (13)
N1—C2—C1	113.88 (14)	C15—C10—C11	118.52 (16)
N1—C2—H22	108.9 (12)	C15—C10—C9	122.28 (15)
C1—C2—H22	106.2 (12)	C11—C10—C9	119.18 (15)
N1—C2—H23	110.0 (13)	C12—C11—C10	120.63 (18)
C1—C2—H23	107.6 (12)	C12—C11—H11	118.3 (14)
H22—C2—H23	110.1 (17)	C10—C11—H11	121.0 (14)
C1—C3—H31	109.3 (14)	C13—C12—C11	120.32 (19)
C1—C3—H32	109.1 (13)	C13—C12—H12	121.3 (12)
H31—C3—H32	109.1 (16)	C11—C12—H12	118.3 (13)
C1—C3—H33	111.6 (12)	C12—C13—C14	119.54 (17)
H31—C3—H33	110.9 (17)	C12—C13—H13	123.6 (17)
H32—C3—H33	106.7 (17)	C14—C13—H13	116.8 (17)
C1—C4—H41	108.7 (13)	C13—C14—C15	120.62 (19)
C1—C4—H42	110.4 (14)	C13—C14—H14	121.3 (12)
H41—C4—H42	109.9 (19)	C15—C14—H14	118.0 (12)
C1—C4—H43	113.0 (13)	C10—C15—C14	120.35 (18)
H41—C4—H43	105.7 (19)	C10—C15—H15	121.9 (12)
H42—C4—H43	109.0 (17)	C14—C15—H15	117.7 (12)
N1—C5—C6	105.97 (14)	C17—C16—C21	118.60 (16)
N1—C5—H51	110.9 (13)	C17—C16—C9	120.95 (15)
C6—C5—H51	109.6 (12)	C21—C16—C9	120.32 (14)
N1—C5—H52	109.5 (12)	C18—C17—C16	120.70 (17)
C6—C5—H52	114.4 (13)	C18—C17—H17	119.8 (12)
H51—C5—H52	106.5 (18)	C16—C17—H17	119.5 (12)
C5—C6—C7	102.29 (14)	C19—C18—C17	120.38 (17)
C5—C6—H61	110.6 (14)	C19—C18—H18	118.8 (14)
C7—C6—H61	114.9 (15)	C17—C18—H18	120.9 (14)
C5—C6—H62	109.9 (13)	C18—C19—C20	119.25 (17)
C7—C6—H62	109.4 (13)	C18—C19—H19	120.5 (13)
H61—C6—H62	109 (2)	C20—C19—H19	120.3 (13)
C6—C7—C8	102.19 (14)	C21—C20—C19	120.63 (17)
C6—C7—H71	113.1 (15)	C21—C20—H20	120.0 (13)
C8—C7—H71	111.7 (14)	C19—C20—H20	119.3 (13)
C6—C7—H72	110.1 (14)	C20—C21—C16	120.39 (16)
C8—C7—H72	108.6 (14)	C20—C21—H21	119.3 (11)
H71—C7—H72	111 (2)	C16—C21—H21	120.4 (11)
N1—C8—C7	103.45 (13)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
O1—H1···N1	0.84 (3)	1.99 (3)	2.6223 (18)	131 (2)
O2—H2···O1^i	0.85 (3)	1.99 (3)	2.8404 (17)	172 (2)

Symmetry code: (i) −x+1, y−1/2, −z+1/2.

(III) 2-[(2-hydroxyethyl)(methyl)amino]-1,1-diphenylethanol

Crystal data

C17H21NO2	F(000) = 584
Mr = 271.35	Dx = 1.210 Mg m^−3
Monoclinic, P21/n	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2yn	Cell parameters from 4201 reflections
a = 9.3438 (2) Å	θ = 2.4–30.0°
b = 15.9896 (4) Å	µ = 0.08 mm^−1
c = 10.9479 (3) Å	T = 120 K
β = 114.441 (1)°	Block, colourless
V = 1489.08 (6) Å^3	0.30 × 0.20 × 0.20 mm
Z = 4

Data collection

Bruker SMART 1K diffractometer	3416 independent reflections
Radiation source: fine-focus sealed tube	2508 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.039
ω scans	θmax = 27.5°, θmin = 2.4°
Absorption correction: multi-scan (SADABS; Bruker, 2004)	h = −9→12
Tmin = 0.977, Tmax = 0.984	k = −20→17
10283 measured reflections	l = −13→14

Refinement

Refinement on F^2	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F^2 > 2σ(F^2)] = 0.044	H atoms treated by a mixture of independent and constrained refinement
wR(F^2) = 0.097	w = 1/[σ^2(Fo^2) + (0.0376P)^2 + 0.2784P] where P = (Fo^2 + 2Fc^2)/3
S = 1.05	(Δ/σ)max < 0.001
3416 reflections	Δρmax = 0.26 e Å^−3
191 parameters	Δρmin = −0.18 e Å^−3
0 restraints	Extinction correction: SHELXL97 (Sheldrick, 2008), Fc^*=kFc[1+0.001xFc^2λ^3/sin(2θ)]^-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.0050 (15)

Special details

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 (Ų)

	x	y	z	Uiso*/Ueq
N1	0.85622 (13)	0.05759 (7)	0.74752 (11)	0.0209 (3)
O1	1.00400 (13)	−0.06277 (7)	0.64116 (13)	0.0371 (3)
O2	0.80726 (11)	0.09856 (6)	0.49626 (10)	0.0230 (2)
C1	1.09664 (17)	−0.00902 (9)	0.74820 (15)	0.0274 (3)
H1A	1.1236	0.0425	0.7121	0.033*
H1B	1.1956	−0.0374	0.8066	0.033*
C2	1.00289 (17)	0.01278 (9)	0.82778 (14)	0.0263 (3)
H2A	0.9771	−0.0393	0.8633	0.032*
H2B	1.0682	0.0480	0.9052	0.032*
C3	0.74175 (17)	0.05058 (9)	0.80697 (15)	0.0263 (3)
H3A	0.6438	0.0786	0.7489	0.039*
H3B	0.7845	0.0771	0.8956	0.039*
H3C	0.7206	−0.0086	0.8161	0.039*
C4	0.88563 (16)	0.14520 (8)	0.72346 (13)	0.0202 (3)
H4A	0.9992	0.1534	0.7478	0.024*
H4B	0.8545	0.1826	0.7803	0.024*
C5	0.78997 (15)	0.16750 (8)	0.57320 (13)	0.0183 (3)
C6	0.61520 (15)	0.18108 (8)	0.54241 (13)	0.0196 (3)
C7	0.56931 (16)	0.25041 (9)	0.59572 (14)	0.0240 (3)
H7	0.6460	0.2898	0.6486	0.029*
C8	0.41220 (17)	0.26216 (9)	0.57198 (16)	0.0291 (3)
H8	0.3825	0.3094	0.6088	0.035*
C9	0.29885 (17)	0.20507 (10)	0.49461 (15)	0.0315 (4)
H9	0.1916	0.2133	0.4777	0.038*
C10	0.34365 (17)	0.13601 (10)	0.44236 (15)	0.0297 (4)
H10	0.2668	0.0965	0.3902	0.036*
C11	0.50079 (16)	0.12408 (9)	0.46581 (14)	0.0251 (3)
H11	0.5299	0.0766	0.4291	0.030*
C12	0.85580 (15)	0.24542 (8)	0.53429 (13)	0.0184 (3)
C13	0.93583 (16)	0.30651 (8)	0.62954 (14)	0.0233 (3)
H13	0.9503	0.2994	0.7201	0.028*
C14	0.99440 (17)	0.37765 (9)	0.59293 (15)	0.0259 (3)
H14	1.0483	0.4188	0.6584	0.031*
C15	0.97449 (17)	0.38869 (9)	0.46163 (16)	0.0279 (3)
H15	1.0154	0.4371	0.4370	0.033*
C16	0.89443 (18)	0.32875 (9)	0.36600 (15)	0.0270 (3)
H16	0.8799	0.3364	0.2756	0.032*
C17	0.83539 (16)	0.25766 (8)	0.40184 (14)	0.0219 (3)
H17	0.7807	0.2170	0.3356	0.026*
H1	1.060 (2)	−0.0751 (12)	0.596 (2)	0.062 (6)*
H2	0.816 (2)	0.0551 (12)	0.547 (2)	0.053 (6)*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
N1	0.0188 (6)	0.0214 (6)	0.0233 (6)	0.0025 (5)	0.0096 (5)	0.0037 (5)
O1	0.0323 (6)	0.0335 (6)	0.0558 (8)	−0.0081 (5)	0.0285 (6)	−0.0159 (6)
O2	0.0292 (5)	0.0184 (5)	0.0228 (5)	−0.0001 (4)	0.0124 (4)	−0.0018 (4)
C1	0.0211 (7)	0.0259 (7)	0.0338 (8)	0.0039 (6)	0.0100 (6)	0.0018 (6)
C2	0.0254 (8)	0.0269 (7)	0.0243 (7)	0.0061 (6)	0.0078 (6)	0.0069 (6)
C3	0.0256 (7)	0.0293 (7)	0.0271 (7)	0.0028 (6)	0.0142 (6)	0.0054 (6)
C4	0.0203 (7)	0.0210 (7)	0.0187 (7)	0.0000 (6)	0.0073 (5)	0.0002 (5)
C5	0.0211 (7)	0.0171 (6)	0.0174 (6)	−0.0018 (5)	0.0085 (5)	−0.0023 (5)
C6	0.0199 (7)	0.0222 (7)	0.0160 (6)	−0.0010 (5)	0.0066 (5)	0.0048 (5)
C7	0.0233 (7)	0.0238 (7)	0.0245 (7)	−0.0009 (6)	0.0096 (6)	0.0028 (6)
C8	0.0274 (8)	0.0292 (8)	0.0351 (8)	0.0069 (6)	0.0173 (7)	0.0093 (7)
C9	0.0184 (7)	0.0433 (9)	0.0320 (8)	0.0036 (7)	0.0097 (6)	0.0144 (7)
C10	0.0219 (7)	0.0399 (9)	0.0231 (7)	−0.0086 (7)	0.0052 (6)	0.0041 (7)
C11	0.0258 (7)	0.0276 (8)	0.0193 (7)	−0.0037 (6)	0.0068 (6)	0.0020 (6)
C12	0.0157 (6)	0.0193 (7)	0.0201 (6)	0.0015 (5)	0.0074 (5)	0.0001 (5)
C13	0.0229 (7)	0.0250 (7)	0.0221 (7)	−0.0012 (6)	0.0095 (6)	−0.0009 (6)
C14	0.0246 (7)	0.0214 (7)	0.0333 (8)	−0.0046 (6)	0.0136 (6)	−0.0037 (6)
C15	0.0302 (8)	0.0197 (7)	0.0408 (9)	−0.0001 (6)	0.0219 (7)	0.0021 (6)
C16	0.0329 (8)	0.0275 (7)	0.0256 (8)	0.0054 (6)	0.0170 (6)	0.0057 (6)
C17	0.0236 (7)	0.0218 (7)	0.0213 (7)	0.0023 (6)	0.0102 (6)	−0.0006 (6)

Geometric parameters (Å, º)

N1—C3	1.4684 (17)	C6—C7	1.4002 (19)
N1—C4	1.4722 (16)	C7—C8	1.394 (2)
N1—C2	1.4721 (17)	C7—H7	0.9500
O1—C1	1.4219 (18)	C8—C9	1.389 (2)
O1—H1	0.88 (2)	C8—H8	0.9500
O2—C5	1.4364 (15)	C9—C10	1.386 (2)
O2—H2	0.87 (2)	C9—H9	0.9500
C1—C2	1.510 (2)	C10—C11	1.395 (2)
C1—H1A	0.9900	C10—H10	0.9500
C1—H1B	0.9900	C11—H11	0.9500
C2—H2A	0.9900	C12—C17	1.3959 (19)
C2—H2B	0.9900	C12—C13	1.3984 (19)
C3—H3A	0.9800	C13—C14	1.3913 (19)
C3—H3B	0.9800	C13—H13	0.9500
C3—H3C	0.9800	C14—C15	1.382 (2)
C4—C5	1.5541 (18)	C14—H14	0.9500
C4—H4A	0.9900	C15—C16	1.388 (2)
C4—H4B	0.9900	C15—H15	0.9500
C5—C12	1.5261 (18)	C16—C17	1.3891 (19)
C5—C6	1.5402 (18)	C16—H16	0.9500
C6—C11	1.3909 (19)	C17—H17	0.9500
C3—N1—C4	112.09 (11)	C11—C6—C5	121.36 (12)
C3—N1—C2	111.55 (11)	C7—C6—C5	120.01 (12)
C4—N1—C2	111.92 (11)	C8—C7—C6	120.64 (13)
C1—O1—H1	107.3 (14)	C8—C7—H7	119.7
C5—O2—H2	104.0 (13)	C6—C7—H7	119.7
O1—C1—C2	108.32 (12)	C9—C8—C7	120.23 (14)
O1—C1—H1A	110.0	C9—C8—H8	119.9
C2—C1—H1A	110.0	C7—C8—H8	119.9
O1—C1—H1B	110.0	C10—C9—C8	119.41 (14)
C2—C1—H1B	110.0	C10—C9—H9	120.3
H1A—C1—H1B	108.4	C8—C9—H9	120.3
N1—C2—C1	112.77 (11)	C9—C10—C11	120.51 (14)
N1—C2—H2A	109.0	C9—C10—H10	119.7
C1—C2—H2A	109.0	C11—C10—H10	119.7
N1—C2—H2B	109.0	C6—C11—C10	120.61 (14)
C1—C2—H2B	109.0	C6—C11—H11	119.7
H2A—C2—H2B	107.8	C10—C11—H11	119.7
N1—C3—H3A	109.5	C17—C12—C13	118.55 (12)
N1—C3—H3B	109.5	C17—C12—C5	120.45 (12)
H3A—C3—H3B	109.5	C13—C12—C5	121.00 (12)
N1—C3—H3C	109.5	C14—C13—C12	120.59 (13)
H3A—C3—H3C	109.5	C14—C13—H13	119.7
H3B—C3—H3C	109.5	C12—C13—H13	119.7
N1—C4—C5	109.85 (10)	C15—C14—C13	120.29 (14)
N1—C4—H4A	109.7	C15—C14—H14	119.9
C5—C4—H4A	109.7	C13—C14—H14	119.9
N1—C4—H4B	109.7	C14—C15—C16	119.65 (13)
C5—C4—H4B	109.7	C14—C15—H15	120.2
H4A—C4—H4B	108.2	C16—C15—H15	120.2
O2—C5—C12	107.87 (10)	C15—C16—C17	120.34 (13)
O2—C5—C6	110.25 (10)	C15—C16—H16	119.8
C12—C5—C6	109.70 (10)	C17—C16—H16	119.8
O2—C5—C4	106.84 (10)	C16—C17—C12	120.57 (13)
C12—C5—C4	111.16 (10)	C16—C17—H17	119.7
C6—C5—C4	110.94 (10)	C12—C17—H17	119.7
C11—C6—C7	118.59 (13)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
O2—H2···N1	0.87 (2)	2.07 (2)	2.6765 (15)	126.0 (16)
O1—H1···O2^i	0.88 (2)	1.93 (2)	2.8101 (15)	177 (2)

Symmetry code: (i) −x+2, −y, −z+1.

(IV) 1-[(2-hydroxy-2-methylpropyl)(1-phenylethyl)amino]- 2-methylpropan-2-ol

Crystal data

C16H27NO2	F(000) = 584
Mr = 265.39	Dx = 1.092 Mg m^−3
Orthorhombic, P212121	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2ac 2ab	Cell parameters from 4891 reflections
a = 8.6781 (5) Å	θ = 2.8–28.7°
b = 12.8084 (7) Å	µ = 0.07 mm^−1
c = 14.5243 (8) Å	T = 120 K
V = 1614.41 (16) Å^3	Block, colourless
Z = 4	0.30 × 0.25 × 0.20 mm

Data collection

Bruker SMART 1K diffractometer	2428 independent reflections
Radiation source: fine-focus sealed tube	1986 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.039
ω scans	θmax = 29.0°, θmin = 2.1°
Absorption correction: multi-scan (SADABS; Bruker, 2004)	h = −11→11
Tmin = 0.979, Tmax = 0.986	k = −7→17
11540 measured reflections	l = −19→19

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)] = 0.041	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.095	H atoms treated by a mixture of independent and constrained refinement
S = 1.06	w = 1/[σ^2(Fo^2) + (0.0435P)^2 + 0.1881P] where P = (Fo^2 + 2Fc^2)/3
2428 reflections	(Δ/σ)max < 0.001
185 parameters	Δρmax = 0.17 e Å^−3
0 restraints	Δρmin = −0.18 e Å^−3

Special details

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 (Ų)

	x	y	z	Uiso*/Ueq
N1	0.33183 (16)	0.03617 (11)	−0.00955 (10)	0.0249 (3)
O1	0.10809 (16)	−0.14653 (9)	0.01479 (9)	0.0297 (3)
O2	0.40324 (16)	−0.18861 (9)	−0.03175 (9)	0.0320 (3)
C1	0.4068 (2)	0.14075 (13)	−0.00743 (12)	0.0296 (4)
H1A	0.5147	0.1301	−0.0296	0.036*
C2	0.3331 (3)	0.22025 (15)	−0.07315 (14)	0.0412 (5)
H2A	0.3319	0.1917	−0.1357	0.062*
H2B	0.3931	0.2851	−0.0724	0.062*
H2C	0.2273	0.2348	−0.0533	0.062*
C3	0.4195 (2)	0.17997 (15)	0.09170 (13)	0.0339 (4)
C4	0.4949 (3)	0.11861 (18)	0.15682 (15)	0.0454 (5)
H4	0.5368	0.0531	0.1390	0.055*
C5	0.5098 (3)	0.1519 (2)	0.24784 (17)	0.0622 (8)
H5	0.5596	0.1085	0.2917	0.075*
C6	0.4526 (4)	0.2473 (2)	0.27417 (18)	0.0727 (9)
H6	0.4637	0.2702	0.3360	0.087*
C7	0.3794 (4)	0.3092 (2)	0.21094 (18)	0.0697 (9)
H7	0.3396	0.3752	0.2292	0.084*
C8	0.3629 (3)	0.27612 (18)	0.11993 (15)	0.0478 (6)
H8	0.3123	0.3200	0.0767	0.057*
C11	0.1692 (2)	0.04041 (13)	0.01720 (13)	0.0284 (4)
H11A	0.1059	0.0470	−0.0392	0.034*
H11B	0.1523	0.1040	0.0546	0.034*
C12	0.1122 (2)	−0.05432 (13)	0.07207 (12)	0.0296 (4)
C13	0.2141 (3)	−0.07307 (16)	0.15569 (12)	0.0391 (5)
H13A	0.1701	−0.1292	0.1932	0.059*
H13B	0.2203	−0.0090	0.1924	0.059*
H13C	0.3177	−0.0931	0.1353	0.059*
C14	−0.0548 (2)	−0.03491 (17)	0.09920 (16)	0.0432 (5)
H14A	−0.0951	−0.0962	0.1317	0.065*
H14B	−0.1164	−0.0223	0.0437	0.065*
H14C	−0.0605	0.0262	0.1396	0.065*
C21	0.3589 (2)	−0.01954 (13)	−0.09660 (11)	0.0293 (4)
H21A	0.3987	0.0310	−0.1423	0.035*
H21B	0.2588	−0.0457	−0.1197	0.035*
C22	0.4715 (2)	−0.11187 (14)	−0.09130 (13)	0.0317 (4)
C23	0.4893 (3)	−0.15751 (18)	−0.18736 (14)	0.0543 (7)
H23A	0.5557	−0.2193	−0.1846	0.081*
H23B	0.5358	−0.1053	−0.2281	0.081*
H23C	0.3878	−0.1773	−0.2113	0.081*
C24	0.6267 (2)	−0.07987 (16)	−0.05172 (17)	0.0453 (5)
H24A	0.6950	−0.1407	−0.0496	0.068*
H24B	0.6122	−0.0524	0.0107	0.068*
H24C	0.6727	−0.0258	−0.0907	0.068*
H1	0.196 (4)	−0.163 (2)	0.0063 (17)	0.064 (9)*
H2	0.470 (3)	−0.242 (2)	−0.0305 (17)	0.063 (8)*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
N1	0.0237 (7)	0.0204 (6)	0.0307 (7)	−0.0014 (6)	−0.0026 (6)	0.0011 (6)
O1	0.0305 (7)	0.0232 (6)	0.0355 (6)	−0.0047 (5)	0.0035 (6)	−0.0051 (5)
O2	0.0319 (7)	0.0239 (6)	0.0402 (7)	0.0062 (6)	0.0054 (6)	0.0077 (5)
C1	0.0290 (9)	0.0251 (8)	0.0348 (9)	−0.0066 (7)	−0.0018 (8)	0.0035 (7)
C2	0.0545 (13)	0.0259 (9)	0.0431 (11)	−0.0026 (9)	−0.0091 (10)	0.0053 (8)
C3	0.0290 (9)	0.0352 (10)	0.0375 (9)	−0.0155 (8)	−0.0017 (8)	−0.0003 (8)
C4	0.0426 (12)	0.0487 (13)	0.0449 (11)	−0.0154 (11)	−0.0135 (10)	0.0026 (10)
C5	0.0657 (16)	0.0780 (18)	0.0429 (11)	−0.0374 (15)	−0.0192 (12)	0.0082 (14)
C6	0.098 (2)	0.080 (2)	0.0400 (13)	−0.0490 (18)	−0.0003 (14)	−0.0118 (13)
C7	0.100 (2)	0.0548 (15)	0.0544 (15)	−0.0259 (16)	0.0164 (17)	−0.0199 (13)
C8	0.0574 (14)	0.0396 (11)	0.0464 (12)	−0.0132 (11)	0.0058 (11)	−0.0047 (10)
C11	0.0250 (8)	0.0229 (8)	0.0374 (9)	0.0004 (7)	−0.0047 (8)	−0.0036 (7)
C12	0.0300 (9)	0.0256 (8)	0.0331 (9)	−0.0059 (7)	0.0020 (8)	−0.0070 (7)
C13	0.0471 (12)	0.0392 (11)	0.0310 (10)	−0.0110 (10)	0.0001 (9)	0.0005 (8)
C14	0.0349 (10)	0.0374 (10)	0.0575 (13)	−0.0071 (9)	0.0110 (10)	−0.0145 (10)
C21	0.0360 (10)	0.0259 (8)	0.0259 (8)	0.0012 (7)	−0.0022 (8)	0.0042 (7)
C22	0.0365 (10)	0.0253 (8)	0.0333 (9)	0.0046 (8)	0.0057 (8)	0.0061 (7)
C23	0.0846 (19)	0.0402 (13)	0.0381 (11)	0.0200 (13)	0.0136 (12)	0.0034 (9)
C24	0.0293 (10)	0.0357 (10)	0.0709 (14)	0.0025 (8)	0.0046 (10)	0.0069 (10)

Geometric parameters (Å, º)

N1—C11	1.465 (2)	C8—H8	0.9500
N1—C21	1.471 (2)	C11—C12	1.534 (2)
N1—C1	1.489 (2)	C11—H11A	0.9900
O1—C12	1.445 (2)	C11—H11B	0.9900
O1—H1	0.80 (3)	C12—C13	1.522 (3)
O2—C22	1.437 (2)	C12—C14	1.523 (3)
O2—H2	0.89 (3)	C13—H13A	0.9800
C1—C3	1.529 (2)	C13—H13B	0.9800
C1—C2	1.535 (3)	C13—H13C	0.9800
C1—H1A	1.0000	C14—H14A	0.9800
C2—H2A	0.9800	C14—H14B	0.9800
C2—H2B	0.9800	C14—H14C	0.9800
C2—H2C	0.9800	C21—C22	1.536 (2)
C3—C8	1.388 (3)	C21—H21A	0.9900
C3—C4	1.393 (3)	C21—H21B	0.9900
C4—C5	1.395 (3)	C22—C23	1.521 (3)
C4—H4	0.9500	C22—C24	1.520 (3)
C5—C6	1.372 (4)	C23—H23A	0.9800
C5—H5	0.9500	C23—H23B	0.9800
C6—C7	1.370 (4)	C23—H23C	0.9800
C6—H6	0.9500	C24—H24A	0.9800
C7—C8	1.396 (3)	C24—H24B	0.9800
C7—H7	0.9500	C24—H24C	0.9800
C11—N1—C21	113.58 (14)	O1—C12—C14	105.01 (14)
C11—N1—C1	112.45 (13)	C13—C12—C14	111.89 (16)
C21—N1—C1	112.60 (13)	O1—C12—C11	110.82 (14)
C12—O1—H1	106.5 (19)	C13—C12—C11	110.61 (15)
C22—O2—H2	105.7 (17)	C14—C12—C11	108.20 (16)
N1—C1—C3	110.28 (14)	C12—C13—H13A	109.5
N1—C1—C2	113.69 (15)	C12—C13—H13B	109.5
C3—C1—C2	113.44 (16)	H13A—C13—H13B	109.5
N1—C1—H1A	106.3	C12—C13—H13C	109.5
C3—C1—H1A	106.3	H13A—C13—H13C	109.5
C2—C1—H1A	106.3	H13B—C13—H13C	109.5
C1—C2—H2A	109.5	C12—C14—H14A	109.5
C1—C2—H2B	109.5	C12—C14—H14B	109.5
H2A—C2—H2B	109.5	H14A—C14—H14B	109.5
C1—C2—H2C	109.5	C12—C14—H14C	109.5
H2A—C2—H2C	109.5	H14A—C14—H14C	109.5
H2B—C2—H2C	109.5	H14B—C14—H14C	109.5
C8—C3—C4	117.8 (2)	N1—C21—C22	115.61 (14)
C8—C3—C1	122.96 (18)	N1—C21—H21A	108.4
C4—C3—C1	119.22 (18)	C22—C21—H21A	108.4
C3—C4—C5	121.0 (2)	N1—C21—H21B	108.4
C3—C4—H4	119.5	C22—C21—H21B	108.4
C5—C4—H4	119.5	H21A—C21—H21B	107.4
C6—C5—C4	120.2 (3)	O2—C22—C23	109.34 (16)
C6—C5—H5	119.9	O2—C22—C24	108.78 (16)
C4—C5—H5	119.9	C23—C22—C24	111.15 (19)
C7—C6—C5	119.8 (2)	O2—C22—C21	107.13 (14)
C7—C6—H6	120.1	C23—C22—C21	108.34 (16)
C5—C6—H6	120.1	C24—C22—C21	112.01 (15)
C6—C7—C8	120.4 (3)	C22—C23—H23A	109.5
C6—C7—H7	119.8	C22—C23—H23B	109.5
C8—C7—H7	119.8	H23A—C23—H23B	109.5
C3—C8—C7	120.9 (3)	C22—C23—H23C	109.5
C3—C8—H8	119.6	H23A—C23—H23C	109.5
C7—C8—H8	119.6	H23B—C23—H23C	109.5
N1—C11—C12	114.78 (15)	C22—C24—H24A	109.5
N1—C11—H11A	108.6	C22—C24—H24B	109.5
C12—C11—H11A	108.6	H24A—C24—H24B	109.5
N1—C11—H11B	108.6	C22—C24—H24C	109.5
C12—C11—H11B	108.6	H24A—C24—H24C	109.5
H11A—C11—H11B	107.5	H24B—C24—H24C	109.5
O1—C12—C13	110.17 (15)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
O1—H1···O2	0.80 (3)	1.91 (3)	2.703 (2)	170 (3)
O2—H2···O1^i	0.89 (3)	1.88 (3)	2.7713 (18)	174 (2)

Symmetry code: (i) x+1/2, −y−1/2, −z.

(V) 1-[(2-Hydroxy-2-phenylethyl)(1-phenylethyl)amino]- 2-methylpropan-2-ol

Crystal data

C20H27NO2	F(000) = 680
Mr = 313.43	Dx = 1.131 Mg m^−3
Orthorhombic, P212121	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2ac 2ab	Cell parameters from 5538 reflections
a = 8.9681 (8) Å	θ = 2.5–29.4°
b = 12.5151 (11) Å	µ = 0.07 mm^−1
c = 16.3960 (14) Å	T = 120 K
V = 1840.2 (3) Å^3	Block, colourless
Z = 4	0.25 × 0.20 × 0.10 mm

Data collection

Bruker SMART 1K diffractometer	2772 independent reflections
Radiation source: fine-focus sealed tube	2376 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.045
ω scans	θmax = 29.0°, θmin = 2.1°
Absorption correction: multi-scan (SADABS; Bruker, 2004)	h = −6→12
Tmin = 0.982, Tmax = 0.993	k = −17→15
13036 measured reflections	l = −16→22

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)] = 0.040	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.086	H atoms treated by a mixture of independent and constrained refinement
S = 1.07	w = 1/[σ^2(Fo^2) + (0.0347P)^2 + 0.2857P] where P = (Fo^2 + 2Fc^2)/3
2772 reflections	(Δ/σ)max < 0.001
219 parameters	Δρmax = 0.25 e Å^−3
0 restraints	Δρmin = −0.19 e Å^−3

Special details

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 (Ų)

	x	y	z	Uiso*/Ueq
N1	0.85952 (16)	0.77498 (11)	0.19666 (9)	0.0187 (3)
O1	1.09159 (15)	0.79961 (11)	0.07312 (8)	0.0242 (3)
O2	0.82898 (15)	0.69725 (11)	0.03022 (8)	0.0244 (3)
C1	0.74550 (19)	0.79181 (14)	0.26025 (10)	0.0205 (3)
H11	0.6548	0.7518	0.2422	0.025*
C2	0.7875 (2)	0.74692 (15)	0.34383 (11)	0.0283 (4)
H2A	0.8006	0.6694	0.3398	0.042*
H2B	0.7080	0.7629	0.3830	0.042*
H2C	0.8808	0.7797	0.3623	0.042*
C3	0.70169 (19)	0.90978 (15)	0.26258 (11)	0.0214 (4)
C4	0.7442 (2)	0.97833 (15)	0.32537 (12)	0.0266 (4)
H4	0.7999	0.9513	0.3701	0.032*
C5	0.7059 (2)	1.08579 (16)	0.32311 (13)	0.0302 (4)
H5	0.7364	1.1319	0.3660	0.036*
C6	0.6240 (2)	1.12599 (16)	0.25894 (14)	0.0326 (5)
H6	0.5986	1.1997	0.2574	0.039*
C7	0.5788 (2)	1.05855 (15)	0.19666 (13)	0.0310 (4)
H7	0.5214	1.0857	0.1526	0.037*
C8	0.6173 (2)	0.95203 (15)	0.19879 (12)	0.0256 (4)
H8	0.5857	0.9063	0.1559	0.031*
C11	0.8686 (2)	0.66259 (13)	0.17157 (10)	0.0199 (4)
H11A	0.8371	0.6167	0.2177	0.024*
H11B	0.9736	0.6450	0.1586	0.024*
C12	0.7717 (2)	0.63768 (13)	0.09766 (10)	0.0199 (4)
H12	0.6668	0.6605	0.1089	0.024*
C13	0.7751 (2)	0.51779 (14)	0.08189 (10)	0.0208 (4)
C14	0.6618 (2)	0.45290 (15)	0.11208 (12)	0.0270 (4)
H14	0.5791	0.4841	0.1394	0.032*
C15	0.6691 (3)	0.34255 (16)	0.10237 (13)	0.0352 (5)
H15	0.5915	0.2986	0.1232	0.042*
C16	0.7885 (3)	0.29681 (17)	0.06266 (12)	0.0371 (5)
H16	0.7937	0.2214	0.0567	0.044*
C17	0.9011 (3)	0.36087 (16)	0.03131 (12)	0.0338 (5)
H17	0.9827	0.3294	0.0033	0.041*
C18	0.8944 (2)	0.47086 (16)	0.04095 (11)	0.0260 (4)
H18	0.9717	0.5145	0.0195	0.031*
C21	1.0045 (2)	0.82471 (14)	0.21296 (10)	0.0194 (3)
H21A	1.0741	0.7695	0.2334	0.023*
H21B	0.9923	0.8790	0.2564	0.023*
C22	1.0727 (2)	0.87806 (14)	0.13747 (10)	0.0203 (4)
C23	0.9759 (2)	0.96925 (16)	0.10625 (13)	0.0308 (4)
H23A	1.0221	1.0007	0.0577	0.046*
H23B	0.9666	1.0239	0.1487	0.046*
H23C	0.8768	0.9418	0.0922	0.046*
C24	1.2299 (2)	0.91583 (15)	0.15766 (12)	0.0258 (4)
H24A	1.2707	0.9553	0.1111	0.039*
H24B	1.2933	0.8539	0.1693	0.039*
H24C	1.2268	0.9626	0.2056	0.039*
H2	0.753 (3)	0.701 (2)	−0.0058 (16)	0.056 (8)*
H1	1.005 (3)	0.7799 (18)	0.0595 (14)	0.041 (7)*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
N1	0.0182 (7)	0.0190 (7)	0.0190 (7)	−0.0023 (6)	0.0016 (6)	−0.0007 (6)
O1	0.0208 (7)	0.0315 (7)	0.0203 (6)	−0.0060 (6)	0.0035 (5)	−0.0054 (5)
O2	0.0262 (7)	0.0267 (7)	0.0202 (6)	−0.0055 (6)	−0.0051 (6)	0.0049 (5)
C1	0.0181 (8)	0.0214 (8)	0.0219 (8)	−0.0035 (7)	0.0028 (7)	−0.0002 (7)
C2	0.0366 (11)	0.0270 (9)	0.0213 (9)	0.0014 (9)	0.0073 (8)	0.0024 (8)
C3	0.0158 (8)	0.0238 (8)	0.0248 (9)	−0.0023 (7)	0.0049 (7)	0.0006 (7)
C4	0.0205 (9)	0.0289 (10)	0.0304 (10)	−0.0013 (8)	0.0009 (8)	−0.0032 (8)
C5	0.0224 (9)	0.0278 (9)	0.0405 (11)	−0.0026 (8)	0.0019 (8)	−0.0083 (9)
C6	0.0231 (9)	0.0228 (9)	0.0519 (13)	0.0018 (8)	0.0048 (10)	0.0007 (9)
C7	0.0212 (9)	0.0315 (11)	0.0405 (11)	0.0008 (8)	−0.0010 (9)	0.0079 (9)
C8	0.0198 (8)	0.0293 (10)	0.0277 (9)	−0.0027 (8)	0.0016 (8)	−0.0017 (8)
C11	0.0208 (8)	0.0190 (8)	0.0200 (8)	−0.0007 (7)	−0.0011 (7)	0.0001 (7)
C12	0.0195 (8)	0.0193 (8)	0.0208 (8)	−0.0012 (7)	0.0000 (7)	0.0011 (7)
C13	0.0233 (9)	0.0215 (9)	0.0176 (8)	−0.0002 (7)	−0.0058 (7)	−0.0008 (7)
C14	0.0288 (10)	0.0265 (9)	0.0258 (9)	−0.0032 (8)	−0.0017 (8)	−0.0008 (8)
C15	0.0476 (13)	0.0250 (10)	0.0330 (11)	−0.0089 (10)	−0.0061 (10)	0.0021 (8)
C16	0.0575 (14)	0.0223 (10)	0.0313 (11)	0.0031 (11)	−0.0142 (10)	−0.0036 (8)
C17	0.0416 (12)	0.0364 (11)	0.0234 (9)	0.0130 (10)	−0.0065 (9)	−0.0091 (9)
C18	0.0250 (9)	0.0321 (10)	0.0208 (9)	0.0018 (8)	−0.0027 (8)	−0.0008 (8)
C21	0.0178 (8)	0.0202 (8)	0.0203 (8)	−0.0013 (7)	0.0015 (7)	−0.0011 (7)
C22	0.0200 (8)	0.0200 (8)	0.0208 (8)	−0.0025 (7)	0.0023 (7)	−0.0012 (7)
C23	0.0266 (10)	0.0312 (10)	0.0344 (10)	−0.0001 (9)	0.0055 (9)	0.0095 (9)
C24	0.0217 (9)	0.0278 (9)	0.0280 (9)	−0.0041 (8)	0.0038 (8)	−0.0048 (8)

Geometric parameters (Å, º)

N1—C21	1.466 (2)	C11—H11B	0.9900
N1—C11	1.468 (2)	C12—C13	1.523 (2)
N1—C1	1.475 (2)	C12—H12	1.0000
O1—C22	1.451 (2)	C13—C18	1.393 (3)
O1—H1	0.84 (3)	C13—C14	1.392 (3)
O2—C12	1.429 (2)	C14—C15	1.392 (3)
O2—H2	0.90 (3)	C14—H14	0.9500
C1—C2	1.528 (2)	C15—C16	1.378 (3)
C1—C3	1.528 (2)	C15—H15	0.9500
C1—H11	1.0000	C16—C17	1.388 (3)
C2—H2A	0.9800	C16—H16	0.9500
C2—H2B	0.9800	C17—C18	1.387 (3)
C2—H2C	0.9800	C17—H17	0.9500
C3—C4	1.393 (3)	C18—H18	0.9500
C3—C8	1.395 (3)	C21—C22	1.534 (2)
C4—C5	1.388 (3)	C21—H21A	0.9900
C4—H4	0.9500	C21—H21B	0.9900
C5—C6	1.378 (3)	C22—C23	1.522 (3)
C5—H5	0.9500	C22—C24	1.523 (3)
C6—C7	1.385 (3)	C23—H23A	0.9800
C6—H6	0.9500	C23—H23B	0.9800
C7—C8	1.378 (3)	C23—H23C	0.9800
C7—H7	0.9500	C24—H24A	0.9800
C8—H8	0.9500	C24—H24B	0.9800
C11—C12	1.523 (2)	C24—H24C	0.9800
C11—H11A	0.9900
C21—N1—C11	114.14 (14)	C13—C12—H12	109.4
C21—N1—C1	115.16 (13)	C11—C12—H12	109.4
C11—N1—C1	111.92 (13)	C18—C13—C14	119.09 (17)
C22—O1—H1	106.6 (16)	C18—C13—C12	120.83 (17)
C12—O2—H2	105.3 (17)	C14—C13—C12	120.00 (17)
N1—C1—C2	114.23 (15)	C15—C14—C13	120.3 (2)
N1—C1—C3	109.50 (13)	C15—C14—H14	119.9
C2—C1—C3	113.34 (15)	C13—C14—H14	119.9
N1—C1—H11	106.4	C16—C15—C14	120.2 (2)
C2—C1—H11	106.4	C16—C15—H15	119.9
C3—C1—H11	106.4	C14—C15—H15	119.9
C1—C2—H2A	109.5	C15—C16—C17	120.03 (19)
C1—C2—H2B	109.5	C15—C16—H16	120.0
H2A—C2—H2B	109.5	C17—C16—H16	120.0
C1—C2—H2C	109.5	C18—C17—C16	120.0 (2)
H2A—C2—H2C	109.5	C18—C17—H17	120.0
H2B—C2—H2C	109.5	C16—C17—H17	120.0
C4—C3—C8	117.97 (17)	C17—C18—C13	120.42 (19)
C4—C3—C1	122.88 (16)	C17—C18—H18	119.8
C8—C3—C1	119.14 (16)	C13—C18—H18	119.8
C5—C4—C3	120.60 (19)	N1—C21—C22	113.05 (14)
C5—C4—H4	119.7	N1—C21—H21A	109.0
C3—C4—H4	119.7	C22—C21—H21A	109.0
C6—C5—C4	120.38 (19)	N1—C21—H21B	109.0
C6—C5—H5	119.8	C22—C21—H21B	109.0
C4—C5—H5	119.8	H21A—C21—H21B	107.8
C5—C6—C7	119.74 (18)	O1—C22—C23	109.22 (15)
C5—C6—H6	120.1	O1—C22—C24	105.07 (14)
C7—C6—H6	120.1	C23—C22—C24	111.58 (15)
C8—C7—C6	119.85 (19)	O1—C22—C21	109.81 (13)
C8—C7—H7	120.1	C23—C22—C21	111.73 (15)
C6—C7—H7	120.1	C24—C22—C21	109.21 (15)
C7—C8—C3	121.45 (19)	C22—C23—H23A	109.5
C7—C8—H8	119.3	C22—C23—H23B	109.5
C3—C8—H8	119.3	H23A—C23—H23B	109.5
N1—C11—C12	112.80 (14)	C22—C23—H23C	109.5
N1—C11—H11A	109.0	H23A—C23—H23C	109.5
C12—C11—H11A	109.0	H23B—C23—H23C	109.5
N1—C11—H11B	109.0	C22—C24—H24A	109.5
C12—C11—H11B	109.0	C22—C24—H24B	109.5
H11A—C11—H11B	107.8	H24A—C24—H24B	109.5
O2—C12—C13	112.05 (14)	C22—C24—H24C	109.5
O2—C12—C11	107.67 (14)	H24A—C24—H24C	109.5
C13—C12—C11	108.99 (14)	H24B—C24—H24C	109.5
O2—C12—H12	109.4

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
O1—H1···O2	0.84 (3)	1.95 (3)	2.7717 (19)	165 (2)
O2—H2···O1^i	0.90 (3)	1.82 (3)	2.7211 (18)	175 (2)

Symmetry code: (i) x−1/2, −y+3/2, −z.

(VI_100) 2-[(2-hydroxyethyl)(methyl)amino]-1,2-diphenylethanol

Crystal data

C17H21NO2	F(000) = 584
Mr = 271.35	Dx = 1.208 Mg m^−3
Monoclinic, P21/n	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2yn	Cell parameters from 5344 reflections
a = 9.5577 (9) Å	θ = 2.4–30.4°
b = 9.9481 (9) Å	µ = 0.08 mm^−1
c = 15.9403 (15) Å	T = 100 K
β = 100.136 (2)°	Plate, colourless
V = 1492.0 (2) Å^3	0.18 × 0.16 × 0.04 mm
Z = 4

Data collection

Bruker SMART 1K diffractometer	2932 independent reflections
Radiation source: fine-focus sealed tube	2482 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.022
ω scans	θmax = 26.0°, θmin = 2.3°
Absorption correction: multi-scan (SADABS; Bruker, 2004)	h = −9→11
Tmin = 0.986, Tmax = 0.997	k = −12→11
7956 measured reflections	l = −19→14

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)] = 0.038	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.092	H atoms treated by a mixture of independent and constrained refinement
S = 1.07	w = 1/[σ^2(Fo^2) + (0.0395P)^2 + 0.4707P] where P = (Fo^2 + 2Fc^2)/3
2932 reflections	(Δ/σ)max < 0.001
195 parameters	Δρmax = 0.24 e Å^−3
0 restraints	Δρmin = −0.25 e Å^−3

Special details

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 (Ų)

	x	y	z	Uiso*/Ueq	Occ. (<1)
N1	0.13144 (11)	0.27954 (10)	0.52216 (6)	0.0168 (2)
O1	0.37764 (12)	0.44412 (10)	0.52060 (7)	0.0256 (2)
H1A	0.296 (5)	0.473 (4)	0.501 (2)	0.038*	0.490 (18)
H1B	0.450 (3)	0.487 (4)	0.504 (2)	0.038*	0.510 (18)
O2	−0.10814 (12)	0.43810 (9)	0.53834 (6)	0.0216 (2)
H2A	−0.191 (4)	0.472 (4)	0.514 (2)	0.032*	0.490 (18)
H2B	−0.043 (4)	0.460 (3)	0.510 (2)	0.032*	0.510 (18)
C1	0.38458 (14)	0.30256 (13)	0.50782 (8)	0.0219 (3)
H11A	0.4813	0.2698	0.5315	0.026*
H11B	0.3654	0.2827	0.4460	0.026*
C2	0.27655 (13)	0.23023 (13)	0.55095 (8)	0.0193 (3)
H21A	0.2799	0.1328	0.5388	0.023*
H21B	0.3023	0.2426	0.6134	0.023*
C3	0.07927 (14)	0.24067 (14)	0.43373 (8)	0.0233 (3)
H3A	0.1532	0.2578	0.3995	0.035*
H3B	−0.0056	0.2934	0.4111	0.035*
H3C	0.0553	0.1448	0.4313	0.035*
C4	0.03329 (13)	0.23669 (12)	0.57829 (8)	0.0163 (3)
H4A	0.0255	0.1365	0.5750	0.020*
C5	−0.11683 (13)	0.29630 (12)	0.54587 (8)	0.0171 (3)
H5	−0.1530	0.2584	0.4880	0.021*
C6	0.06569 (14)	0.18334 (14)	0.73457 (8)	0.0214 (3)
H6	0.0287	0.0964	0.7191	0.026*
C7	0.10109 (15)	0.21730 (15)	0.82022 (8)	0.0274 (3)
H7	0.0888	0.1541	0.8630	0.033*
C8	0.15458 (15)	0.34431 (15)	0.84275 (9)	0.0283 (3)
H8	0.1770	0.3691	0.9011	0.034*
C9	0.17529 (14)	0.43510 (14)	0.78005 (9)	0.0251 (3)
H9	0.2139	0.5214	0.7958	0.030*
C10	0.14015 (13)	0.40100 (13)	0.69453 (8)	0.0200 (3)
H10	0.1547	0.4638	0.6520	0.024*
C11	0.08351 (13)	0.27458 (13)	0.67089 (8)	0.0172 (3)
C12	−0.21970 (13)	0.25736 (13)	0.60404 (8)	0.0169 (3)
C13	−0.26413 (13)	0.34890 (13)	0.65996 (8)	0.0203 (3)
H13	−0.2319	0.4393	0.6612	0.024*
C14	−0.35558 (14)	0.30825 (14)	0.71397 (8)	0.0248 (3)
H14	−0.3861	0.3714	0.7517	0.030*
C15	−0.40267 (14)	0.17624 (15)	0.71330 (8)	0.0248 (3)
H15	−0.4647	0.1490	0.7506	0.030*
C16	−0.35869 (14)	0.08426 (14)	0.65787 (8)	0.0233 (3)
H16	−0.3902	−0.0064	0.6573	0.028*
C17	−0.26856 (13)	0.12498 (13)	0.60331 (8)	0.0199 (3)
H17	−0.2397	0.0620	0.5649	0.024*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
N1	0.0166 (5)	0.0185 (5)	0.0156 (5)	0.0007 (4)	0.0036 (4)	0.0009 (4)
O1	0.0182 (5)	0.0206 (5)	0.0385 (6)	−0.0013 (4)	0.0070 (4)	0.0044 (4)
O2	0.0200 (5)	0.0174 (5)	0.0280 (5)	0.0015 (4)	0.0058 (4)	0.0074 (4)
C1	0.0197 (7)	0.0224 (7)	0.0243 (7)	0.0035 (5)	0.0057 (5)	0.0018 (5)
C2	0.0188 (6)	0.0188 (6)	0.0206 (6)	0.0033 (5)	0.0042 (5)	0.0017 (5)
C3	0.0225 (7)	0.0288 (7)	0.0190 (6)	0.0000 (5)	0.0049 (5)	−0.0014 (5)
C4	0.0183 (6)	0.0119 (6)	0.0189 (6)	−0.0002 (5)	0.0038 (5)	0.0010 (5)
C5	0.0174 (6)	0.0156 (6)	0.0180 (6)	−0.0013 (5)	0.0018 (5)	0.0011 (5)
C6	0.0202 (6)	0.0216 (7)	0.0230 (7)	0.0022 (5)	0.0049 (5)	0.0035 (5)
C7	0.0258 (7)	0.0367 (8)	0.0202 (7)	0.0092 (6)	0.0055 (5)	0.0086 (6)
C8	0.0264 (7)	0.0396 (9)	0.0178 (6)	0.0119 (6)	0.0003 (5)	−0.0035 (6)
C9	0.0203 (7)	0.0267 (7)	0.0265 (7)	0.0047 (6)	−0.0008 (5)	−0.0070 (6)
C10	0.0179 (6)	0.0189 (6)	0.0230 (7)	0.0020 (5)	0.0032 (5)	0.0001 (5)
C11	0.0137 (6)	0.0191 (6)	0.0189 (6)	0.0029 (5)	0.0034 (5)	0.0013 (5)
C12	0.0139 (6)	0.0186 (6)	0.0171 (6)	−0.0005 (5)	−0.0004 (5)	0.0027 (5)
C13	0.0210 (6)	0.0193 (7)	0.0202 (6)	−0.0027 (5)	0.0026 (5)	0.0001 (5)
C14	0.0260 (7)	0.0283 (7)	0.0210 (6)	−0.0003 (6)	0.0065 (5)	−0.0024 (6)
C15	0.0218 (7)	0.0332 (8)	0.0203 (6)	−0.0054 (6)	0.0057 (5)	0.0055 (6)
C16	0.0212 (7)	0.0216 (7)	0.0255 (7)	−0.0055 (5)	0.0003 (5)	0.0060 (5)
C17	0.0187 (6)	0.0180 (6)	0.0222 (6)	0.0004 (5)	0.0012 (5)	0.0014 (5)

Geometric parameters (Å, º)

N1—C3	1.4621 (16)	C6—C7	1.3892 (19)
N1—C2	1.4666 (16)	C6—C11	1.3944 (18)
N1—C4	1.4689 (15)	C6—H6	0.9500
O1—C1	1.4261 (16)	C7—C8	1.386 (2)
O1—H1A	0.83 (5)	C7—H7	0.9500
O1—H1B	0.89 (3)	C8—C9	1.387 (2)
O2—C5	1.4194 (15)	C8—H8	0.9500
O2—H2A	0.88 (4)	C9—C10	1.3874 (18)
O2—H2B	0.85 (3)	C9—H9	0.9500
C1—C2	1.5186 (18)	C10—C11	1.3947 (18)
C1—H11A	0.9900	C10—H10	0.9500
C1—H11B	0.9900	C12—C13	1.3919 (18)
C2—H21A	0.9900	C12—C17	1.3967 (18)
C2—H21B	0.9900	C13—C14	1.3905 (18)
C3—H3A	0.9800	C13—H13	0.9500
C3—H3B	0.9800	C14—C15	1.388 (2)
C3—H3C	0.9800	C14—H14	0.9500
C4—C11	1.5172 (17)	C15—C16	1.388 (2)
C4—C5	1.5545 (17)	C15—H15	0.9500
C4—H4A	1.0000	C16—C17	1.3879 (19)
C5—C12	1.5156 (17)	C16—H16	0.9500
C5—H5	1.0000	C17—H17	0.9500
C3—N1—C2	110.88 (10)	C4—C5—H5	108.2
C3—N1—C4	111.38 (10)	C7—C6—C11	121.15 (13)
C2—N1—C4	112.49 (9)	C7—C6—H6	119.4
C1—O1—H1A	110 (3)	C11—C6—H6	119.4
C1—O1—H1B	112 (2)	C8—C7—C6	119.42 (13)
H1A—O1—H1B	116 (3)	C8—C7—H7	120.3
C5—O2—H2A	111 (2)	C6—C7—H7	120.3
C5—O2—H2B	111 (2)	C7—C8—C9	119.98 (12)
H2A—O2—H2B	111 (3)	C7—C8—H8	120.0
O1—C1—C2	110.53 (11)	C9—C8—H8	120.0
O1—C1—H11A	109.5	C8—C9—C10	120.54 (13)
C2—C1—H11A	109.5	C8—C9—H9	119.7
O1—C1—H11B	109.5	C10—C9—H9	119.7
C2—C1—H11B	109.5	C9—C10—C11	120.09 (12)
H11A—C1—H11B	108.1	C9—C10—H10	120.0
N1—C2—C1	112.38 (10)	C11—C10—H10	120.0
N1—C2—H21A	109.1	C6—C11—C10	118.79 (12)
C1—C2—H21A	109.1	C6—C11—C4	119.23 (11)
N1—C2—H21B	109.1	C10—C11—C4	121.89 (11)
C1—C2—H21B	109.1	C13—C12—C17	118.88 (11)
H21A—C2—H21B	107.9	C13—C12—C5	121.90 (11)
N1—C3—H3A	109.5	C17—C12—C5	119.20 (11)
N1—C3—H3B	109.5	C14—C13—C12	120.14 (12)
H3A—C3—H3B	109.5	C14—C13—H13	119.9
N1—C3—H3C	109.5	C12—C13—H13	119.9
H3A—C3—H3C	109.5	C15—C14—C13	120.59 (13)
H3B—C3—H3C	109.5	C15—C14—H14	119.7
N1—C4—C11	113.20 (10)	C13—C14—H14	119.7
N1—C4—C5	109.75 (9)	C16—C15—C14	119.65 (12)
C11—C4—C5	110.13 (10)	C16—C15—H15	120.2
N1—C4—H4A	107.9	C14—C15—H15	120.2
C11—C4—H4A	107.9	C15—C16—C17	119.84 (12)
C5—C4—H4A	107.9	C15—C16—H16	120.1
O2—C5—C12	111.08 (10)	C17—C16—H16	120.1
O2—C5—C4	110.05 (10)	C16—C17—C12	120.90 (12)
C12—C5—C4	111.06 (10)	C16—C17—H17	119.6
O2—C5—H5	108.2	C12—C17—H17	119.6
C12—C5—H5	108.2
C3—N1—C2—C1	69.45 (14)	C9—C10—C11—C4	175.32 (11)
C4—N1—C2—C1	−165.08 (10)	N1—C4—C11—C6	−139.83 (11)
O1—C1—C2—N1	55.99 (14)	C5—C4—C11—C6	96.90 (13)
C3—N1—C4—C11	179.80 (10)	N1—C4—C11—C10	43.69 (16)
C2—N1—C4—C11	54.61 (14)	C5—C4—C11—C10	−79.58 (14)
C3—N1—C4—C5	−56.72 (13)	O2—C5—C12—C13	−17.12 (16)
C2—N1—C4—C5	178.09 (10)	C4—C5—C12—C13	105.71 (13)
N1—C4—C5—O2	−54.85 (13)	O2—C5—C12—C17	164.63 (11)
C11—C4—C5—O2	70.41 (12)	C4—C5—C12—C17	−72.53 (14)
N1—C4—C5—C12	−178.28 (10)	C17—C12—C13—C14	0.03 (18)
C11—C4—C5—C12	−53.01 (13)	C5—C12—C13—C14	−178.22 (12)
C11—C6—C7—C8	0.2 (2)	C12—C13—C14—C15	0.5 (2)
C6—C7—C8—C9	−1.4 (2)	C13—C14—C15—C16	−0.4 (2)
C7—C8—C9—C10	1.3 (2)	C14—C15—C16—C17	−0.3 (2)
C8—C9—C10—C11	−0.01 (19)	C15—C16—C17—C12	0.82 (19)
C7—C6—C11—C10	1.06 (19)	C13—C12—C17—C16	−0.69 (18)
C7—C6—C11—C4	−175.53 (12)	C5—C12—C17—C16	177.61 (11)
C9—C10—C11—C6	−1.17 (18)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
O1—H1B···O1^i	0.89 (3)	1.89 (3)	2.771 (2)	170 (3)
O1—H1A···O2^ii	0.83 (5)	2.01 (5)	2.8353 (16)	173 (4)
O2—H2A···O1^ii	0.88 (4)	1.96 (4)	2.8353 (16)	171 (3)
O2—H2B···O2^ii	0.85 (3)	2.03 (3)	2.859 (2)	164 (3)

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

(VI_300) 2-[(2-hydroxyethyl)(methyl)amino]-1,2-diphenylethanol

Crystal data

C17H21NO2	F(000) = 584
Mr = 271.35	Dx = 1.173 Mg m^−3
Monoclinic, P21/n	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2yn	Cell parameters from 3073 reflections
a = 9.5879 (5) Å	θ = 2.4–28.7°
b = 10.0655 (6) Å	µ = 0.08 mm^−1
c = 16.1252 (9) Å	T = 300 K
β = 99.034 (1)°	Plate, colourless
V = 1536.89 (15) Å^3	0.18 × 0.16 × 0.04 mm
Z = 4

Data collection

Bruker SMART 1K diffractometer	3025 independent reflections
Radiation source: fine-focus sealed tube	2099 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.027
ω scans	θmax = 26.0°, θmin = 2.3°
Absorption correction: multi-scan (SADABS; Bruker, 2004)	h = −11→9
Tmin = 0.986, Tmax = 0.997	k = −12→11
8282 measured reflections	l = −14→19

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)] = 0.044	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.113	H atoms treated by a mixture of independent and constrained refinement
S = 1.06	w = 1/[σ^2(Fo^2) + (0.0518P)^2 + 0.1373P] where P = (Fo^2 + 2Fc^2)/3
3025 reflections	(Δ/σ)max < 0.001
195 parameters	Δρmax = 0.18 e Å^−3
0 restraints	Δρmin = −0.16 e Å^−3

Special details

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 (Ų)

	x	y	z	Uiso*/Ueq	Occ. (<1)
N1	0.13034 (12)	0.28024 (12)	0.52004 (7)	0.0410 (3)
O1	0.37554 (17)	0.44375 (14)	0.51848 (10)	0.0698 (4)
H1A	0.292 (7)	0.477 (5)	0.501 (3)	0.105*	0.51 (2)
H1B	0.461 (6)	0.502 (6)	0.513 (4)	0.105*	0.49 (2)
O2	−0.10849 (16)	0.43621 (12)	0.53813 (8)	0.0543 (3)
H2A	−0.190 (6)	0.475 (5)	0.518 (3)	0.081*	0.51 (2)
H2B	−0.041 (5)	0.461 (4)	0.518 (3)	0.081*	0.49 (2)
C1	0.38199 (17)	0.30547 (19)	0.50519 (12)	0.0600 (5)
H11A	0.4759	0.2734	0.5272	0.072*
H11B	0.3642	0.2872	0.4454	0.072*
C2	0.27463 (16)	0.23294 (16)	0.54767 (10)	0.0501 (4)
H21A	0.2792	0.1387	0.5357	0.060*
H21B	0.2983	0.2446	0.6080	0.060*
C3	0.08071 (19)	0.2418 (2)	0.43275 (10)	0.0630 (5)
H3A	0.1530	0.2603	0.3994	0.095*
H3B	−0.0028	0.2914	0.4114	0.095*
H3C	0.0594	0.1486	0.4302	0.095*
C4	0.03132 (15)	0.23746 (14)	0.57566 (9)	0.0391 (3)
H4A	0.0234	0.1405	0.5717	0.047*
C5	−0.11738 (15)	0.29667 (15)	0.54522 (9)	0.0421 (4)
H5	−0.1520	0.2606	0.4893	0.051*
C6	0.06436 (19)	0.18146 (19)	0.72902 (11)	0.0588 (5)
H6	0.0286	0.0975	0.7140	0.071*
C7	0.1006 (2)	0.2136 (3)	0.81363 (12)	0.0817 (7)
H7	0.0891	0.1515	0.8547	0.098*
C8	0.1530 (2)	0.3369 (3)	0.83594 (13)	0.0860 (7)
H8	0.1760	0.3593	0.8924	0.103*
C9	0.1719 (2)	0.4274 (2)	0.77537 (12)	0.0706 (6)
H9	0.2093	0.5107	0.7909	0.085*
C10	0.13587 (17)	0.39601 (17)	0.69139 (10)	0.0524 (4)
H10	0.1488	0.4585	0.6508	0.063*
C11	0.08071 (15)	0.27249 (15)	0.66697 (9)	0.0410 (4)
C12	−0.22040 (15)	0.25797 (15)	0.60285 (9)	0.0414 (4)
C13	−0.26360 (17)	0.34606 (17)	0.65922 (10)	0.0525 (4)
H13	−0.2307	0.4331	0.6616	0.063*
C14	−0.3560 (2)	0.3055 (2)	0.71241 (11)	0.0685 (5)
H14	−0.3852	0.3659	0.7498	0.082*
C15	−0.4043 (2)	0.1778 (2)	0.71042 (12)	0.0715 (6)
H15	−0.4655	0.1513	0.7467	0.086*
C16	−0.3627 (2)	0.08911 (19)	0.65501 (12)	0.0659 (5)
H16	−0.3949	0.0019	0.6537	0.079*
C17	−0.27270 (17)	0.12926 (17)	0.60097 (11)	0.0532 (4)
H17	−0.2466	0.0689	0.5625	0.064*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
N1	0.0377 (7)	0.0473 (7)	0.0389 (6)	0.0005 (5)	0.0086 (5)	0.0019 (5)
O1	0.0403 (8)	0.0620 (9)	0.1083 (11)	−0.0016 (6)	0.0156 (7)	0.0194 (7)
O2	0.0408 (7)	0.0498 (7)	0.0741 (8)	0.0036 (5)	0.0144 (6)	0.0241 (6)
C1	0.0414 (10)	0.0757 (13)	0.0658 (11)	0.0097 (8)	0.0178 (8)	0.0088 (9)
C2	0.0440 (9)	0.0512 (10)	0.0569 (10)	0.0098 (7)	0.0134 (7)	0.0056 (7)
C3	0.0591 (11)	0.0854 (13)	0.0464 (10)	−0.0034 (9)	0.0139 (8)	−0.0076 (9)
C4	0.0402 (8)	0.0346 (8)	0.0430 (8)	−0.0018 (6)	0.0086 (6)	0.0021 (6)
C5	0.0368 (8)	0.0475 (9)	0.0415 (8)	−0.0046 (6)	0.0046 (6)	0.0047 (7)
C6	0.0568 (11)	0.0676 (12)	0.0532 (10)	0.0085 (9)	0.0125 (8)	0.0182 (9)
C7	0.0769 (14)	0.121 (2)	0.0493 (11)	0.0318 (14)	0.0152 (10)	0.0301 (12)
C8	0.0772 (15)	0.130 (2)	0.0462 (11)	0.0363 (15)	−0.0035 (10)	−0.0117 (13)
C9	0.0571 (11)	0.0864 (15)	0.0635 (12)	0.0110 (10)	−0.0052 (9)	−0.0226 (11)
C10	0.0468 (9)	0.0577 (11)	0.0511 (10)	0.0034 (8)	0.0029 (7)	−0.0049 (8)
C11	0.0334 (8)	0.0482 (9)	0.0416 (8)	0.0064 (6)	0.0062 (6)	0.0061 (7)
C12	0.0332 (8)	0.0463 (9)	0.0431 (8)	−0.0031 (6)	0.0015 (6)	0.0065 (7)
C13	0.0520 (10)	0.0550 (10)	0.0514 (10)	−0.0087 (8)	0.0112 (8)	−0.0005 (8)
C14	0.0703 (13)	0.0843 (14)	0.0555 (11)	−0.0065 (11)	0.0243 (9)	−0.0044 (9)
C15	0.0634 (12)	0.0957 (16)	0.0591 (11)	−0.0186 (11)	0.0210 (9)	0.0162 (11)
C16	0.0582 (11)	0.0608 (12)	0.0777 (13)	−0.0204 (9)	0.0075 (10)	0.0188 (10)
C17	0.0452 (9)	0.0495 (10)	0.0646 (10)	−0.0076 (8)	0.0075 (8)	0.0034 (8)

Geometric parameters (Å, º)

N1—C2	1.4647 (19)	C6—C11	1.384 (2)
N1—C3	1.4653 (19)	C6—C7	1.392 (3)
N1—C4	1.4692 (18)	C6—H6	0.9300
O1—C1	1.411 (2)	C7—C8	1.366 (3)
O1—H1A	0.87 (7)	C7—H7	0.9300
O1—H1B	1.02 (6)	C8—C9	1.369 (3)
O2—C5	1.4129 (19)	C8—H8	0.9300
O2—H2A	0.89 (6)	C9—C10	1.381 (2)
O2—H2B	0.81 (5)	C9—H9	0.9300
C1—C2	1.511 (2)	C10—C11	1.384 (2)
C1—H11A	0.9700	C10—H10	0.9300
C1—H11B	0.9700	C12—C13	1.379 (2)
C2—H21A	0.9700	C12—C17	1.388 (2)
C2—H21B	0.9700	C13—C14	1.388 (2)
C3—H3A	0.9600	C13—H13	0.9300
C3—H3B	0.9600	C14—C15	1.364 (3)
C3—H3C	0.9600	C14—H14	0.9300
C4—C11	1.516 (2)	C15—C16	1.367 (3)
C4—C5	1.552 (2)	C15—H15	0.9300
C4—H4A	0.9800	C16—C17	1.379 (2)
C5—C12	1.510 (2)	C16—H16	0.9300
C5—H5	0.9800	C17—H17	0.9300
C2—N1—C3	110.80 (13)	C4—C5—H5	108.1
C2—N1—C4	112.90 (11)	C11—C6—C7	121.04 (19)
C3—N1—C4	111.44 (12)	C11—C6—H6	119.5
C1—O1—H1A	113 (3)	C7—C6—H6	119.5
C1—O1—H1B	120 (3)	C8—C7—C6	119.62 (19)
H1A—O1—H1B	117 (5)	C8—C7—H7	120.2
C5—O2—H2A	114 (3)	C6—C7—H7	120.2
C5—O2—H2B	114 (3)	C7—C8—C9	120.10 (19)
H2A—O2—H2B	115 (4)	C7—C8—H8	119.9
O1—C1—C2	111.01 (14)	C9—C8—H8	119.9
O1—C1—H11A	109.4	C8—C9—C10	120.4 (2)
C2—C1—H11A	109.4	C8—C9—H9	119.8
O1—C1—H11B	109.4	C10—C9—H9	119.8
C2—C1—H11B	109.4	C9—C10—C11	120.69 (17)
H11A—C1—H11B	108.0	C9—C10—H10	119.7
N1—C2—C1	112.53 (13)	C11—C10—H10	119.7
N1—C2—H21A	109.1	C6—C11—C10	118.08 (15)
C1—C2—H21A	109.1	C6—C11—C4	119.65 (15)
N1—C2—H21B	109.1	C10—C11—C4	122.18 (13)
C1—C2—H21B	109.1	C13—C12—C17	118.02 (15)
H21A—C2—H21B	107.8	C13—C12—C5	122.21 (14)
N1—C3—H3A	109.5	C17—C12—C5	119.76 (14)
N1—C3—H3B	109.5	C12—C13—C14	120.33 (16)
H3A—C3—H3B	109.5	C12—C13—H13	119.8
N1—C3—H3C	109.5	C14—C13—H13	119.8
H3A—C3—H3C	109.5	C15—C14—C13	120.67 (18)
H3B—C3—H3C	109.5	C15—C14—H14	119.7
N1—C4—C11	113.05 (12)	C13—C14—H14	119.7
N1—C4—C5	110.12 (11)	C14—C15—C16	119.84 (17)
C11—C4—C5	110.45 (12)	C14—C15—H15	120.1
N1—C4—H4A	107.7	C16—C15—H15	120.1
C11—C4—H4A	107.7	C15—C16—C17	119.84 (17)
C5—C4—H4A	107.7	C15—C16—H16	120.1
O2—C5—C12	111.09 (13)	C17—C16—H16	120.1
O2—C5—C4	110.07 (12)	C16—C17—C12	121.29 (17)
C12—C5—C4	111.32 (11)	C16—C17—H17	119.4
O2—C5—H5	108.1	C12—C17—H17	119.4
C12—C5—H5	108.1

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
O1—H1B···O1^i	1.02 (6)	1.81 (6)	2.789 (3)	160 (5)
O1—H1A···O2^ii	0.87 (7)	1.98 (7)	2.849 (2)	177 (5)
O2—H2A···O1^ii	0.89 (6)	1.96 (6)	2.849 (2)	176 (4)
O2—H2B···O2^ii	0.81 (5)	2.09 (4)	2.880 (3)	168 (4)

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