(11R,12S)-16-Amino-tetra-cyclo-[6.6.2.0(2,7).0(9,14)]hexa-deca-2(7),3,5,9(14),10,12-hexaen-15-ol.

In the title compound, C(16)H(15)NO, the dihedral angle between the outer benzene rings is 51.88 (6)°, and each of the central six-membered rings has a boat conformation. The hy-droxy and amino groups are syn, and the hy-droxy H atom forms an intra-molecular O-H⋯N hydrogen bond. In the crystal, mol-ecules assemble via C-H⋯O and C-H⋯π inter-actions, consolidating a three-dimensional architecture.

Related literature

For chiral ligands in asymmetric catalytic reactions, see: Yamakuchi et al. (2005 ▶). For the synthesis of the title compound, see: Hashimoto et al. (1998 ▶); Matsunaga et al. (2005 ▶). For a related structure, see: Abdel-Aziz et al. (2012 ▶).

Experimental

Crystal data

C16H15NO

M = 237.29

Monoclinic,

a = 8.6224 (2) Å

b = 7.1140 (1) Å

c = 10.0210 (2) Å

β = 106.707 (2)°

V = 588.74 (2) Å3

Z = 2

Cu Kα radiation

μ = 0.65 mm−1

T = 100 K

0.40 × 0.30 × 0.20 mm

Data collection

Agilent SuperNova Dual diffractometer with an Atlas detector

Absorption correction: multi-scan (CrysAlis PRO; Agilent, 2012 ▶) T min = 0.590, T max = 1.000

4044 measured reflections

2375 independent reflections

2357 reflections with I > 2σ(I)

R int = 0.011

Refinement

R[F 2 > 2σ(F 2)] = 0.029

wR(F 2) = 0.077

S = 1.06

2375 reflections

175 parameters

1 restraint

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.20 e Å−3

Δρmin = −0.17 e Å−3

Absolute structure: Flack (1983 ▶), 1060 Friedel pairs

Flack parameter: 0.0 (2)

Data collection: CrysAlis PRO (Agilent, 2012 ▶); cell refinement: CrysAlis PRO; data reduction: CrysAlis PRO; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: ORTEP-3 (Farrugia, 1997 ▶) and DIAMOND (Brandenburg, 2006 ▶); software used to prepare material for publication: publCIF (Westrip, 2010 ▶).

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S1600536812026542/pv2558sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536812026542/pv2558Isup2.hkl

Additional supplementary materials: crystallographic information; 3D view; checkCIF report

C16H15NO	F(000) = 252
Mr = 237.29	Dx = 1.339 Mg m−3
Monoclinic, P21	Cu Kα radiation, λ = 1.54184 Å
Hall symbol: P 2yb	Cell parameters from 3312 reflections
a = 8.6224 (2) Å	θ = 4.6–76.4°
b = 7.1140 (1) Å	µ = 0.65 mm−1
c = 10.0210 (2) Å	T = 100 K
β = 106.707 (2)°	Prism, colourless
V = 588.74 (2) Å3	0.40 × 0.30 × 0.20 mm
Z = 2

Agilent SuperNova Dual diffractometer with an Atlas detector	2375 independent reflections
Radiation source: SuperNova (Cu) X-ray Source	2357 reflections with I > 2σ(I)
Mirror monochromator	Rint = 0.011
Detector resolution: 10.4041 pixels mm-1	θmax = 76.6°, θmin = 4.6°
ω scan	h = −10→10
Absorption correction: multi-scan (CrysAlis PRO; Agilent, 2012)	k = −8→8
Tmin = 0.590, Tmax = 1.000	l = −12→7
4044 measured reflections

Refinement on F2	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.029	H atoms treated by a mixture of independent and constrained refinement
wR(F2) = 0.077	w = 1/[σ2(Fo2) + (0.0469P)2 + 0.1178P] where P = (Fo2 + 2Fc2)/3
S = 1.06	(Δ/σ)max < 0.001
2375 reflections	Δρmax = 0.20 e Å−3
175 parameters	Δρmin = −0.17 e Å−3
1 restraint	Absolute structure: Flack (1983), 1060 Friedel pairs
Primary atom site location: structure-invariant direct methods	Flack parameter: 0.0 (2)

	x	y	z	Uiso*/Ueq
O1	0.49638 (11)	0.50034 (15)	0.64491 (10)	0.0241 (2)
N1	0.71887 (14)	0.29044 (18)	0.80145 (14)	0.0240 (3)
C1	0.96576 (14)	0.71372 (17)	0.75647 (12)	0.0142 (2)
C2	1.12329 (14)	0.73301 (18)	0.74782 (12)	0.0158 (2)
H2	1.2081	0.6575	0.8038	0.019*
C3	1.15501 (14)	0.86460 (19)	0.65592 (12)	0.0160 (2)
H3	1.2620	0.8777	0.6488	0.019*
C4	1.03187 (15)	0.97688 (19)	0.57454 (12)	0.0168 (2)
H4	1.0557	1.0684	0.5142	0.020*
C5	0.87298 (15)	0.95569 (18)	0.58111 (12)	0.0160 (2)
H5	0.7882	1.0306	0.5244	0.019*
C6	0.84091 (15)	0.82368 (17)	0.67170 (12)	0.0144 (3)
C7	0.67531 (14)	0.77274 (18)	0.68480 (12)	0.0151 (2)
H7	0.5883	0.8555	0.6263	0.018*
C8	0.65031 (15)	0.56368 (19)	0.63948 (13)	0.0180 (3)
H8	0.6555	0.5528	0.5414	0.022*
C9	0.78995 (15)	0.43912 (18)	0.73668 (13)	0.0181 (3)
H9	0.8514	0.3787	0.6773	0.022*
C10	0.90784 (14)	0.57079 (17)	0.84339 (13)	0.0150 (3)
H10	0.9998	0.4997	0.9070	0.018*
C11	0.80732 (14)	0.67230 (17)	0.92286 (12)	0.0141 (2)
C12	0.82683 (14)	0.66176 (18)	1.06492 (13)	0.0161 (2)
H12	0.9093	0.5848	1.1225	0.019*
C13	0.72441 (15)	0.76507 (18)	1.12256 (12)	0.0181 (3)
H13	0.7377	0.7591	1.2199	0.022*
C14	0.60311 (15)	0.87664 (18)	1.03815 (13)	0.0178 (3)
H14	0.5346	0.9479	1.0782	0.021*
C15	0.58155 (14)	0.88446 (17)	0.89508 (13)	0.0159 (2)
H15	0.4978	0.9597	0.8374	0.019*
C16	0.68295 (14)	0.78190 (18)	0.83726 (12)	0.0145 (2)
H1o	0.526 (3)	0.384 (4)	0.696 (2)	0.048 (6)*
H1n	0.720 (3)	0.316 (4)	0.891 (3)	0.060 (7)*
H2n	0.772 (3)	0.179 (4)	0.803 (2)	0.043 (5)*

	U11	U22	U33	U12	U13	U23
O1	0.0167 (4)	0.0288 (6)	0.0270 (5)	−0.0084 (4)	0.0067 (4)	−0.0030 (4)
N1	0.0266 (6)	0.0152 (5)	0.0352 (6)	−0.0026 (5)	0.0170 (5)	−0.0005 (5)
C1	0.0170 (5)	0.0130 (6)	0.0131 (5)	−0.0007 (5)	0.0051 (4)	−0.0011 (4)
C2	0.0156 (5)	0.0163 (6)	0.0153 (5)	0.0009 (4)	0.0043 (4)	−0.0019 (4)
C3	0.0143 (5)	0.0184 (6)	0.0161 (5)	−0.0018 (5)	0.0059 (4)	−0.0029 (5)
C4	0.0200 (6)	0.0178 (6)	0.0141 (5)	−0.0025 (5)	0.0072 (4)	0.0004 (5)
C5	0.0178 (6)	0.0161 (6)	0.0135 (5)	0.0023 (5)	0.0036 (4)	0.0000 (4)
C6	0.0143 (5)	0.0156 (6)	0.0141 (5)	−0.0006 (4)	0.0051 (4)	−0.0023 (4)
C7	0.0127 (5)	0.0183 (6)	0.0146 (5)	0.0013 (5)	0.0042 (4)	0.0007 (5)
C8	0.0167 (6)	0.0211 (7)	0.0179 (6)	−0.0030 (5)	0.0075 (5)	−0.0039 (5)
C9	0.0201 (6)	0.0146 (6)	0.0229 (6)	−0.0029 (5)	0.0114 (5)	−0.0029 (5)
C10	0.0148 (5)	0.0141 (6)	0.0171 (6)	0.0006 (4)	0.0064 (4)	0.0017 (4)
C11	0.0149 (5)	0.0120 (6)	0.0162 (6)	−0.0023 (4)	0.0059 (4)	0.0001 (4)
C12	0.0168 (5)	0.0137 (6)	0.0177 (6)	−0.0019 (5)	0.0051 (4)	0.0020 (4)
C13	0.0222 (6)	0.0191 (6)	0.0152 (5)	−0.0057 (5)	0.0088 (5)	−0.0011 (5)
C14	0.0181 (6)	0.0158 (6)	0.0230 (6)	−0.0034 (5)	0.0113 (5)	−0.0040 (5)
C15	0.0132 (5)	0.0146 (6)	0.0206 (6)	−0.0005 (5)	0.0058 (4)	0.0002 (5)
C16	0.0142 (5)	0.0144 (6)	0.0164 (5)	−0.0027 (5)	0.0065 (4)	−0.0003 (5)

O1—C8	1.4174 (15)	C7—C8	1.5518 (17)
O1—H1o	0.96 (3)	C7—H7	1.0000
N1—C9	1.4644 (17)	C8—C9	1.5841 (18)
N1—H1n	0.91 (3)	C8—H8	1.0000
N1—H2n	0.91 (3)	C9—C10	1.5586 (17)
C1—C2	1.3924 (16)	C9—H9	1.0000
C1—C6	1.4024 (16)	C10—C11	1.5177 (16)
C1—C10	1.5140 (16)	C10—H10	1.0000
C2—C3	1.3944 (18)	C11—C12	1.3867 (17)
C2—H2	0.9500	C11—C16	1.4017 (16)
C3—C4	1.3902 (17)	C12—C13	1.3954 (18)
C3—H3	0.9500	C12—H12	0.9500
C4—C5	1.3985 (17)	C13—C14	1.3895 (18)
C4—H4	0.9500	C13—H13	0.9500
C5—C6	1.3881 (17)	C14—C15	1.3928 (18)
C5—H5	0.9500	C14—H14	0.9500
C6—C7	1.5150 (16)	C15—C16	1.3869 (17)
C7—C16	1.5116 (15)	C15—H15	0.9500
C8—O1—H1o	100.4 (13)	C7—C8—H8	108.7
C9—N1—H1n	113.9 (17)	C9—C8—H8	108.7
C9—N1—H2n	110.8 (14)	N1—C9—C10	113.79 (11)
H1n—N1—H2n	107 (2)	N1—C9—C8	109.61 (10)
C2—C1—C6	120.00 (11)	C10—C9—C8	108.43 (10)
C2—C1—C10	126.23 (11)	N1—C9—H9	108.3
C6—C1—C10	113.60 (10)	C10—C9—H9	108.3
C3—C2—C1	119.17 (11)	C8—C9—H9	108.3
C3—C2—H2	120.4	C1—C10—C11	108.35 (10)
C1—C2—H2	120.4	C1—C10—C9	105.47 (10)
C2—C3—C4	120.76 (11)	C11—C10—C9	106.73 (10)
C2—C3—H3	119.6	C1—C10—H10	112.0
C4—C3—H3	119.6	C11—C10—H10	112.0
C3—C4—C5	120.25 (11)	C9—C10—H10	112.0
C3—C4—H4	119.9	C12—C11—C16	120.26 (11)
C5—C4—H4	119.9	C12—C11—C10	126.43 (11)
C6—C5—C4	119.06 (11)	C16—C11—C10	113.29 (10)
C6—C5—H5	120.5	C11—C12—C13	119.47 (11)
C4—C5—H5	120.5	C11—C12—H12	120.3
C5—C6—C1	120.73 (11)	C13—C12—H12	120.3
C5—C6—C7	126.05 (11)	C14—C13—C12	120.27 (11)
C1—C6—C7	113.11 (10)	C14—C13—H13	119.9
C16—C7—C6	108.00 (9)	C12—C13—H13	119.9
C16—C7—C8	107.41 (10)	C13—C14—C15	120.25 (11)
C6—C7—C8	105.01 (10)	C13—C14—H14	119.9
C16—C7—H7	112.0	C15—C14—H14	119.9
C6—C7—H7	112.0	C16—C15—C14	119.70 (11)
C8—C7—H7	112.0	C16—C15—H15	120.2
O1—C8—C7	110.26 (10)	C14—C15—H15	120.2
O1—C8—C9	110.68 (11)	C15—C16—C11	120.02 (11)
C7—C8—C9	109.82 (10)	C15—C16—C7	126.54 (11)
O1—C8—H8	108.7	C11—C16—C7	113.44 (10)
C6—C1—C2—C3	1.06 (17)	C2—C1—C10—C9	−113.84 (13)
C10—C1—C2—C3	176.01 (12)	C6—C1—C10—C9	61.39 (12)
C1—C2—C3—C4	0.59 (18)	N1—C9—C10—C1	−179.42 (10)
C2—C3—C4—C5	−1.72 (19)	C8—C9—C10—C1	−57.17 (11)
C3—C4—C5—C6	1.17 (18)	N1—C9—C10—C11	−64.31 (13)
C4—C5—C6—C1	0.48 (17)	C8—C9—C10—C11	57.94 (12)
C4—C5—C6—C7	−175.42 (11)	C1—C10—C11—C12	−128.68 (13)
C2—C1—C6—C5	−1.61 (17)	C9—C10—C11—C12	118.16 (13)
C10—C1—C6—C5	−177.17 (11)	C1—C10—C11—C16	52.62 (13)
C2—C1—C6—C7	174.79 (11)	C9—C10—C11—C16	−60.54 (13)
C10—C1—C6—C7	−0.77 (14)	C16—C11—C12—C13	−1.70 (18)
C5—C6—C7—C16	−129.68 (13)	C10—C11—C12—C13	179.68 (12)
C1—C6—C7—C16	54.15 (13)	C11—C12—C13—C14	0.43 (18)
C5—C6—C7—C8	115.94 (13)	C12—C13—C14—C15	0.78 (18)
C1—C6—C7—C8	−60.23 (12)	C13—C14—C15—C16	−0.72 (18)
C16—C7—C8—O1	66.32 (12)	C14—C15—C16—C11	−0.55 (17)
C6—C7—C8—O1	−178.88 (10)	C14—C15—C16—C7	179.28 (12)
C16—C7—C8—C9	−55.90 (12)	C12—C11—C16—C15	1.77 (17)
C6—C7—C8—C9	58.89 (12)	C10—C11—C16—C15	−179.44 (11)
O1—C8—C9—N1	1.54 (14)	C12—C11—C16—C7	−178.08 (11)
C7—C8—C9—N1	123.51 (11)	C10—C11—C16—C7	0.71 (14)
O1—C8—C9—C10	−123.22 (11)	C6—C7—C16—C15	126.02 (13)
C7—C8—C9—C10	−1.25 (13)	C8—C7—C16—C15	−121.19 (13)
C2—C1—C10—C11	132.18 (12)	C6—C7—C16—C11	−54.14 (14)
C6—C1—C10—C11	−52.59 (13)	C8—C7—C16—C11	58.65 (12)

D—H···A	D—H	H···A	D···A	D—H···A
O1—H1o···N1	0.96 (3)	1.82 (2)	2.577 (2)	133 (2)
C5—H5···O1i	0.95	2.56	3.3506 (16)	141
C4—H4···Cg1ii	0.95	2.61	3.5064 (14)	158
C10—H10···Cg2iii	1.00	2.95	3.9212 (14)	164
C12—H12···Cg1iii	0.95	2.67	3.5159 (14)	149

Table 1

Hydrogen-bond geometry (Å, °)

Cg1 and Cg2 are the centroids of the C1–C6 and C11–C16 benzene rings, respectively.

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O1—H1o⋯N1	0.96 (3)	1.82 (2)	2.577 (2)	133 (2)
C5—H5⋯O1i	0.95	2.56	3.3506 (16)	141
C4—H4⋯Cg1ii	0.95	2.61	3.5064 (14)	158
C10—H10⋯Cg2iii	1.00	2.95	3.9212 (14)	164
C12—H12⋯Cg1iii	0.95	2.67	3.5159 (14)	149

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