Crystal structure of 3-hy-droxy-methyl-1,2,3,4-tetra-hydro-isoquinolin-1-one.

In the title compound, C10H11NO2, two independent but virtually superimposable mol-ecules, A and B, comprise the asymmetric unit. The heterocyclic ring in each mol-ecule has a screw-boat conformation, and the methyl-hydroxyl group occupies a position to one side of this ring with N-C-C-O torsion angles of -55.30 (15) (mol-ecule A) and -55.94 (16)° (mol-ecule B). In the crystal, O-H⋯O and N-H⋯O hydrogen bonding leads to 11-membered {⋯HNCO⋯HO⋯HNC2O} heterosynthons, involving three different mol-ecules, which are edge-shared to generate a supra-molecular chain along the a axis. Inter-actions of the type C-H⋯O provide additional stability to the chains, and link these into a three-dimensional architecture.

Related literature

For background, including medicinal potential, to compounds related to the title compound, see: Biaggio et al. (2007 ▸); Grunewald et al. (1999 ▸); Zoretic & Soja (1977 ▸). For additional conformational analysis, see: Cremer & Pople (1975 ▸).

Experimental

Crystal data

C10H11NO2

M = 177.20

Orthorhombic,

a = 6.2846 (1) Å

b = 13.8914 (1) Å

c = 19.5592 (2) Å

V = 1707.56 (3) Å3

Z = 8

Cu Kα radiation

μ = 0.79 mm−1

T = 100 K

0.35 × 0.25 × 0.15 mm

Data collection

Agilent SuperNova CCD diffractometer

Absorption correction: multi-scan (CrysAlis PRO; Agilent, 2011 ▸) T min = 0.882, T max = 1.000

6258 measured reflections

3358 independent reflections

3336 reflections with I > 2σ(I)

R int = 0.011

Refinement

R[F 2 > 2σ(F 2)] = 0.026

wR(F 2) = 0.070

S = 1.06

3358 reflections

251 parameters

4 restraints

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.15 e Å−3

Δρmin = −0.29 e Å−3

Absolute structure: Flack x determined using 1359 quotients [(I +)−(I −)]/[(I +)+(I −)] (Parsons et al., 2013 ▸)

Absolute structure parameter: −0.05 (6)

Data collection: CrysAlis PRO (Agilent, 2011 ▸); cell refinement: CrysAlis PRO; data reduction: CrysAlis PRO; program(s) used to solve structure: SIR2014 (Burla et al., 2015 ▸); program(s) used to refine structure: SHELXL2014 (Sheldrick, 2015 ▸); molecular graphics: ORTEP-3 for Windows (Farrugia, 2012 ▸), QMOL (Gans & Shalloway, 2001 ▸) and DIAMOND (Brandenburg, 2006 ▸); software used to prepare material for publication: MarvinSketch (ChemAxon, 2010 ▸) and publCIF (Westrip, 2010 ▸).

Crystal structure: contains datablock(s) I, New_Global_Publ_Block. DOI: 10.1107/S2056989015012670/hg5449sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S2056989015012670/hg5449Isup2.hkl

Click here for additional data file.

Supporting information file. DOI: 10.1107/S2056989015012670/hg5449Isup3.cml

Click here for additional data file.

. DOI: 10.1107/S2056989015012670/hg5449fig1.tif

Reaction scheme for the preparation of the title compound.

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. DOI: 10.1107/S2056989015012670/hg5449fig2.tif

The mol­ecular structures of the two independent mol­ecules in the title compound showing the atom-labelling scheme and displacement ellipsoids at the 70% probability level.

Click here for additional data file.

A B . DOI: 10.1107/S2056989015012670/hg5449fig3.tif

Superimposition of the two independent mol­ecules. Mol­ecule A is shown in blue and B in red. The mol­ecules have been superimposed such that the benzene rings are overlapped.

Click here for additional data file.

a . DOI: 10.1107/S2056989015012670/hg5449fig4.tif

A view of the supra­molecular chain sustained by O—H⋯O and N—H⋯O hydrogen bonds (orange and blue dashed lines, respectively) and aligned along the a axis in the crystal packing.

Click here for additional data file.

a . DOI: 10.1107/S2056989015012670/hg5449fig5.tif

A view in projection down the a axis of the unit-cell contents. The O—H⋯O, N—H⋯O and C—H⋯O inter­actions are shown as orange, blue and purple dashed lines, respectively.

CCDC reference: 1409827

Additional supporting information: crystallographic information; 3D view; checkCIF report

C10H11NO2	Dx = 1.379 Mg m−3
Mr = 177.20	Cu Kα radiation, λ = 1.54184 Å
Orthorhombic, P212121	Cell parameters from 5937 reflections
a = 6.2846 (1) Å	θ = 3.2–74.2°
b = 13.8914 (1) Å	µ = 0.79 mm−1
c = 19.5592 (2) Å	T = 100 K
V = 1707.56 (3) Å3	Prism, colourless
Z = 8	0.35 × 0.25 × 0.15 mm
F(000) = 752

Agilent SuperNova CCD diffractometer	3336 reflections with I > 2σ(I)
Radiation source: SuperNova (Cu) X-ray Source	Rint = 0.011
ω scans	θmax = 74.3°, θmin = 3.9°
Absorption correction: multi-scan (CrysAlis PRO; Agilent, 2011)	h = −7→7
Tmin = 0.882, Tmax = 1.000	k = −17→17
6258 measured reflections	l = −14→24
3358 independent reflections

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)] = 0.026	w = 1/[σ2(Fo2) + (0.0483P)2 + 0.1971P] where P = (Fo2 + 2Fc2)/3
wR(F2) = 0.070	(Δ/σ)max = 0.001
S = 1.06	Δρmax = 0.15 e Å−3
3358 reflections	Δρmin = −0.29 e Å−3
251 parameters	Absolute structure: Flack x determined using 1359 quotients [(I+)-(I-)]/[(I+)+(I-)] (Parsons et al., 2013)
4 restraints	Absolute structure parameter: −0.05 (6)

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.

	x	y	z	Uiso*/Ueq
O1	0.62669 (16)	0.73762 (7)	0.18705 (5)	0.0180 (2)
O2	1.32523 (16)	0.66602 (7)	0.10231 (5)	0.0168 (2)
H2O	1.424 (3)	0.6888 (18)	0.1273 (11)	0.049 (7)*
N1	0.91512 (19)	0.75379 (8)	0.11906 (6)	0.0150 (2)
H1N	0.887 (3)	0.6996 (10)	0.0994 (9)	0.021 (5)*
C1	0.7850 (2)	0.78505 (10)	0.16823 (6)	0.0144 (3)
C2	0.8387 (2)	0.87911 (10)	0.20099 (7)	0.0156 (3)
C3	0.6905 (2)	0.92359 (11)	0.24371 (7)	0.0195 (3)
H3	0.5548	0.8950	0.2507	0.023*
C4	0.7411 (3)	1.00942 (11)	0.27601 (8)	0.0228 (3)
H4	0.6397	1.0401	0.3047	0.027*
C5	0.9411 (3)	1.05064 (11)	0.26623 (8)	0.0212 (3)
H5	0.9764	1.1091	0.2887	0.025*
C6	1.0884 (2)	1.00671 (10)	0.22384 (7)	0.0187 (3)
H6	1.2240	1.0355	0.2172	0.022*
C7	1.0392 (2)	0.92024 (10)	0.19065 (7)	0.0158 (3)
C8	1.1995 (2)	0.86671 (10)	0.14844 (7)	0.0169 (3)
H8A	1.2810	0.8226	0.1784	0.020*
H8B	1.3008	0.9132	0.1282	0.020*
C9	1.0952 (2)	0.80877 (10)	0.09148 (7)	0.0153 (3)
H9	1.0405	0.8544	0.0561	0.018*
C10	1.2538 (2)	0.74041 (10)	0.05779 (7)	0.0163 (3)
H10A	1.1863	0.7108	0.0172	0.020*
H10B	1.3783	0.7779	0.0419	0.020*
O3	0.10908 (16)	0.52866 (7)	−0.04188 (5)	0.0200 (2)
O4	0.80454 (17)	0.57641 (7)	0.04790 (5)	0.0183 (2)
H4O	0.904 (3)	0.5612 (18)	0.0200 (11)	0.050 (7)*
N2	0.3944 (2)	0.49397 (8)	0.02382 (6)	0.0165 (2)
H2N	0.373 (4)	0.5458 (11)	0.0481 (9)	0.028 (5)*
C11	0.2649 (2)	0.47641 (10)	−0.02887 (7)	0.0160 (3)
C12	0.3141 (2)	0.39062 (10)	−0.07222 (7)	0.0174 (3)
C13	0.1653 (2)	0.35932 (11)	−0.12001 (7)	0.0217 (3)
H13	0.0327	0.3916	−0.1242	0.026*
C14	0.2107 (3)	0.28085 (12)	−0.16165 (7)	0.0241 (3)
H14	0.1092	0.2591	−0.1941	0.029*
C15	0.4058 (3)	0.23446 (11)	−0.15537 (8)	0.0249 (3)
H15	0.4370	0.1805	−0.1835	0.030*
C16	0.5553 (3)	0.26632 (11)	−0.10831 (8)	0.0230 (3)
H16	0.6883	0.2342	−0.1047	0.028*
C17	0.5124 (2)	0.34507 (10)	−0.06620 (7)	0.0188 (3)
C18	0.6750 (2)	0.38637 (10)	−0.01815 (8)	0.0208 (3)
H18A	0.7610	0.4350	−0.0428	0.025*
H18B	0.7720	0.3344	−0.0031	0.025*
C19	0.5744 (2)	0.43317 (10)	0.04445 (7)	0.0179 (3)
H19	0.5197	0.3811	0.0751	0.022*
C20	0.7337 (2)	0.49417 (10)	0.08474 (7)	0.0194 (3)
H20A	0.6665	0.5155	0.1279	0.023*
H20B	0.8583	0.4539	0.0966	0.023*

	U11	U22	U33	U12	U13	U23
O1	0.0137 (5)	0.0198 (5)	0.0204 (5)	−0.0022 (4)	0.0008 (4)	−0.0006 (4)
O2	0.0153 (5)	0.0148 (5)	0.0203 (5)	0.0004 (4)	−0.0012 (4)	−0.0004 (4)
N1	0.0141 (5)	0.0138 (5)	0.0171 (5)	−0.0010 (4)	−0.0001 (4)	−0.0022 (4)
C1	0.0131 (6)	0.0157 (6)	0.0145 (6)	0.0020 (5)	−0.0029 (5)	0.0016 (5)
C2	0.0162 (7)	0.0161 (6)	0.0146 (6)	0.0009 (5)	−0.0017 (5)	0.0005 (5)
C3	0.0163 (7)	0.0229 (7)	0.0193 (6)	0.0007 (6)	0.0009 (6)	−0.0021 (5)
C4	0.0222 (7)	0.0242 (7)	0.0219 (7)	0.0035 (6)	0.0021 (6)	−0.0061 (6)
C5	0.0247 (8)	0.0180 (7)	0.0210 (7)	−0.0005 (6)	−0.0045 (6)	−0.0050 (5)
C6	0.0193 (7)	0.0172 (6)	0.0196 (7)	−0.0026 (6)	−0.0027 (5)	−0.0004 (5)
C7	0.0170 (7)	0.0154 (6)	0.0152 (6)	0.0011 (5)	−0.0021 (5)	0.0015 (5)
C8	0.0131 (6)	0.0162 (6)	0.0216 (7)	−0.0017 (5)	0.0005 (6)	−0.0017 (5)
C9	0.0137 (6)	0.0153 (6)	0.0167 (6)	0.0003 (5)	0.0015 (5)	0.0009 (5)
C10	0.0158 (6)	0.0179 (6)	0.0152 (6)	0.0013 (5)	0.0013 (5)	0.0013 (5)
O3	0.0151 (5)	0.0225 (5)	0.0225 (5)	0.0022 (4)	−0.0001 (4)	−0.0020 (4)
O4	0.0162 (5)	0.0161 (5)	0.0227 (5)	−0.0004 (4)	0.0016 (4)	−0.0021 (4)
N2	0.0163 (6)	0.0150 (5)	0.0183 (5)	0.0013 (5)	0.0003 (5)	−0.0032 (4)
C11	0.0143 (6)	0.0167 (6)	0.0172 (6)	−0.0033 (5)	0.0034 (5)	0.0004 (5)
C12	0.0179 (7)	0.0169 (6)	0.0174 (6)	−0.0030 (5)	0.0034 (5)	−0.0017 (5)
C13	0.0191 (7)	0.0253 (7)	0.0206 (7)	−0.0040 (6)	0.0026 (6)	−0.0014 (6)
C14	0.0275 (8)	0.0260 (7)	0.0187 (7)	−0.0089 (6)	0.0018 (6)	−0.0036 (6)
C15	0.0348 (9)	0.0187 (6)	0.0212 (7)	−0.0057 (7)	0.0083 (6)	−0.0046 (6)
C16	0.0250 (7)	0.0173 (7)	0.0267 (7)	0.0007 (6)	0.0057 (6)	−0.0022 (6)
C17	0.0195 (7)	0.0159 (6)	0.0210 (6)	−0.0020 (5)	0.0034 (5)	−0.0006 (5)
C18	0.0156 (7)	0.0180 (6)	0.0288 (7)	0.0018 (5)	−0.0001 (6)	−0.0040 (6)
C19	0.0169 (6)	0.0153 (6)	0.0215 (7)	0.0011 (5)	−0.0018 (5)	0.0019 (5)
C20	0.0185 (7)	0.0200 (6)	0.0198 (6)	−0.0005 (6)	−0.0026 (5)	0.0005 (5)

O1—C1	1.2486 (17)	O3—C11	1.2454 (18)
O2—C10	1.4239 (16)	O4—C20	1.4220 (17)
O2—H2O	0.849 (13)	O4—H4O	0.855 (13)
N1—C1	1.3351 (18)	N2—C11	1.3356 (18)
N1—C9	1.4680 (17)	N2—C19	1.4682 (18)
N1—H1N	0.863 (12)	N2—H2N	0.872 (12)
C1—C2	1.4939 (18)	C11—C12	1.4949 (18)
C2—C3	1.396 (2)	C12—C13	1.392 (2)
C2—C7	1.398 (2)	C12—C17	1.402 (2)
C3—C4	1.386 (2)	C13—C14	1.390 (2)
C3—H3	0.9500	C13—H13	0.9500
C4—C5	1.395 (2)	C14—C15	1.391 (2)
C4—H4	0.9500	C14—H14	0.9500
C5—C6	1.385 (2)	C15—C16	1.388 (2)
C5—H5	0.9500	C15—H15	0.9500
C6—C7	1.400 (2)	C16—C17	1.396 (2)
C6—H6	0.9500	C16—H16	0.9500
C7—C8	1.4997 (19)	C17—C18	1.502 (2)
C8—C9	1.5227 (18)	C18—C19	1.524 (2)
C8—H8A	0.9900	C18—H18A	0.9900
C8—H8B	0.9900	C18—H18B	0.9900
C9—C10	1.5263 (19)	C19—C20	1.5303 (19)
C9—H9	1.0000	C19—H19	1.0000
C10—H10A	0.9900	C20—H20A	0.9900
C10—H10B	0.9900	C20—H20B	0.9900
C10—O2—H2O	108.1 (18)	C20—O4—H4O	110.7 (17)
C1—N1—C9	124.60 (12)	C11—N2—C19	125.20 (12)
C1—N1—H1N	118.7 (14)	C11—N2—H2N	118.6 (14)
C9—N1—H1N	116.5 (14)	C19—N2—H2N	116.2 (14)
O1—C1—N1	121.92 (13)	O3—C11—N2	122.02 (13)
O1—C1—C2	121.01 (12)	O3—C11—C12	120.76 (12)
N1—C1—C2	117.06 (12)	N2—C11—C12	117.21 (12)
C3—C2—C7	120.47 (13)	C13—C12—C17	120.82 (13)
C3—C2—C1	119.55 (13)	C13—C12—C11	119.41 (13)
C7—C2—C1	119.94 (12)	C17—C12—C11	119.73 (13)
C4—C3—C2	120.03 (14)	C14—C13—C12	120.04 (15)
C4—C3—H3	120.0	C14—C13—H13	120.0
C2—C3—H3	120.0	C12—C13—H13	120.0
C3—C4—C5	119.83 (14)	C13—C14—C15	119.50 (14)
C3—C4—H4	120.1	C13—C14—H14	120.3
C5—C4—H4	120.1	C15—C14—H14	120.3
C6—C5—C4	120.26 (13)	C16—C15—C14	120.51 (14)
C6—C5—H5	119.9	C16—C15—H15	119.7
C4—C5—H5	119.9	C14—C15—H15	119.7
C5—C6—C7	120.54 (14)	C15—C16—C17	120.70 (15)
C5—C6—H6	119.7	C15—C16—H16	119.7
C7—C6—H6	119.7	C17—C16—H16	119.7
C2—C7—C6	118.86 (13)	C16—C17—C12	118.42 (14)
C2—C7—C8	118.83 (12)	C16—C17—C18	122.47 (14)
C6—C7—C8	122.17 (13)	C12—C17—C18	119.00 (12)
C7—C8—C9	112.08 (12)	C17—C18—C19	112.53 (12)
C7—C8—H8A	109.2	C17—C18—H18A	109.1
C9—C8—H8A	109.2	C19—C18—H18A	109.1
C7—C8—H8B	109.2	C17—C18—H18B	109.1
C9—C8—H8B	109.2	C19—C18—H18B	109.1
H8A—C8—H8B	107.9	H18A—C18—H18B	107.8
N1—C9—C8	109.74 (11)	N2—C19—C18	110.14 (11)
N1—C9—C10	109.78 (11)	N2—C19—C20	109.10 (11)
C8—C9—C10	111.33 (11)	C18—C19—C20	112.23 (12)
N1—C9—H9	108.6	N2—C19—H19	108.4
C8—C9—H9	108.6	C18—C19—H19	108.4
C10—C9—H9	108.6	C20—C19—H19	108.4
O2—C10—C9	113.17 (11)	O4—C20—C19	112.88 (11)
O2—C10—H10A	108.9	O4—C20—H20A	109.0
C9—C10—H10A	108.9	C19—C20—H20A	109.0
O2—C10—H10B	108.9	O4—C20—H20B	109.0
C9—C10—H10B	108.9	C19—C20—H20B	109.0
H10A—C10—H10B	107.8	H20A—C20—H20B	107.8
C9—N1—C1—O1	175.75 (12)	C19—N2—C11—O3	176.74 (13)
C9—N1—C1—C2	−5.26 (19)	C19—N2—C11—C12	−3.2 (2)
O1—C1—C2—C3	−12.24 (19)	O3—C11—C12—C13	−11.1 (2)
N1—C1—C2—C3	168.76 (13)	N2—C11—C12—C13	168.84 (13)
O1—C1—C2—C7	165.51 (12)	O3—C11—C12—C17	166.40 (13)
N1—C1—C2—C7	−13.49 (18)	N2—C11—C12—C17	−13.68 (19)
C7—C2—C3—C4	0.3 (2)	C17—C12—C13—C14	1.2 (2)
C1—C2—C3—C4	178.05 (13)	C11—C12—C13—C14	178.68 (13)
C2—C3—C4—C5	−0.6 (2)	C12—C13—C14—C15	−0.4 (2)
C3—C4—C5—C6	0.7 (2)	C13—C14—C15—C16	−0.4 (2)
C4—C5—C6—C7	−0.4 (2)	C14—C15—C16—C17	0.3 (2)
C3—C2—C7—C6	0.0 (2)	C15—C16—C17—C12	0.5 (2)
C1—C2—C7—C6	−177.76 (12)	C15—C16—C17—C18	−175.52 (14)
C3—C2—C7—C8	175.65 (13)	C13—C12—C17—C16	−1.3 (2)
C1—C2—C7—C8	−2.08 (18)	C11—C12—C17—C16	−178.75 (13)
C5—C6—C7—C2	0.1 (2)	C13—C12—C17—C18	174.88 (13)
C5—C6—C7—C8	−175.46 (13)	C11—C12—C17—C18	−2.57 (19)
C2—C7—C8—C9	33.21 (17)	C16—C17—C18—C19	−151.24 (14)
C6—C7—C8—C9	−151.25 (13)	C12—C17—C18—C19	32.74 (18)
C1—N1—C9—C8	35.96 (18)	C11—N2—C19—C18	32.98 (18)
C1—N1—C9—C10	158.62 (12)	C11—N2—C19—C20	156.58 (12)
C7—C8—C9—N1	−47.52 (15)	C17—C18—C19—N2	−45.45 (16)
C7—C8—C9—C10	−169.26 (11)	C17—C18—C19—C20	−167.21 (12)
N1—C9—C10—O2	−55.30 (15)	N2—C19—C20—O4	−55.94 (16)
C8—C9—C10—O2	66.42 (15)	C18—C19—C20—O4	66.41 (16)

D—H···A	D—H	H···A	D···A	D—H···A
O2—H2O···O1i	0.85 (1)	1.86 (1)	2.7066 (14)	176 (3)
O4—H4O···O3i	0.86 (1)	1.83 (1)	2.6808 (15)	178 (3)
N1—H1N···O4	0.86 (1)	2.05 (1)	2.9141 (15)	176 (2)
N2—H2N···O2ii	0.87 (1)	2.00 (1)	2.8737 (15)	179 (2)
C4—H4···O2iii	0.95	2.53	3.2512 (18)	132
C8—H8A···O1i	0.99	2.48	3.3157 (16)	142
C18—H18A···O3i	0.99	2.55	3.4007 (16)	145

Table 1

Hydrogen-bond geometry (, )

DHA	DH	HA	D A	DHA
O2H2OO1i	0.85(1)	1.86(1)	2.7066(14)	176(3)
O4H4OO3i	0.86(1)	1.83(1)	2.6808(15)	178(3)
N1H1NO4	0.86(1)	2.05(1)	2.9141(15)	176(2)
N2H2NO2ii	0.87(1)	2.00(1)	2.8737(15)	179(2)
C4H4O2iii	0.95	2.53	3.2512(18)	132
C8H8AO1i	0.99	2.48	3.3157(16)	142
C18H18AO3i	0.99	2.55	3.4007(16)	145

Symmetry codes: (i) ; (ii) ; (iii) .