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The crystal structure of the title compound, C12H20N2O, was determined in order to establish the configuration of C4b (S) and C8a (R) with respect to the known configuration of C1 (R). The compound forms infinite chains of hydrogen-bonded molecules parallel to the c axis.
Supporting information
CCDC reference: 147692
Details of the preparation of (I) are given by Ostendorf et al. (2000). Crystals were obtained after recrystallization from benzene.
Due to the absence of significant anomalous dispersion, the absolute structure cannot be determined reliably. The configuration of C1 was set equal to R, consistent with the starting materials used (see Ostendorf et al., 2000). The 2197 measured reflections reduced to 1924 unique reflections. After merging of the Friedel pairs, 1461 reflections remained. The hydroxyl H atom was located on a difference Fourier map and its coordinates were refined. The other H atoms were also located on a difference Fourier map, but in order to limit the number of refined parameters, they were included in the refinement on calculated positions riding on their carrier atoms. All H-atom displacement parameters were set equal to the equivalent isotropic displacement parameter of their carrier atom, multiplied by a constant factor of 1.5 (hydroxyl H) or 1.2 (other H atoms).
Data collection: locally modified CAD-4 Software (Enraf-Nonius, 1989); cell refinement: SET4 (de Boer & Duisenberg, 1984); data reduction: HELENA (Spek, 1997); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: PLATON (Spek, 2000); software used to prepare material for publication: PLATON.
(1
R,4bS,8aR)-(1,2,3,4 b,5,6,7,8,8a,9a-Decahydro-4,9a-diazafluoren-1-yl)methanol
top
Crystal data top
C12H20N2O | F(000) = 456 |
Mr = 208.30 | Dx = 1.262 Mg m−3 |
Orthorhombic, P212121 | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: P 2ac 2ab | Cell parameters from 24 reflections |
a = 8.4691 (9) Å | θ = 10.1–15.6° |
b = 10.3985 (8) Å | µ = 0.08 mm−1 |
c = 12.4538 (15) Å | T = 150 K |
V = 1096.8 (2) Å3 | Block, colourless |
Z = 4 | 0.3 × 0.2 × 0.1 mm |
Data collection top
Enraf Nonius CAD4T diffractometer | Rint = 0.035 |
Radiation source: Rotating Anode | θmax = 27.5°, θmin = 2.6° |
Graphite monochromator | h = −11→0 |
ω scans | k = −10→13 |
2161 measured reflections | l = 0→16 |
1461 independent reflections | 3 standard reflections every 60 min |
1007 reflections with I > 2σ(I) | intensity decay: 6% |
Refinement top
Refinement on F2 | 0 restraints |
Least-squares matrix: full | H atoms treated by a mixture of independent and constrained refinement |
R[F2 > 2σ(F2)] = 0.050 | w = 1/[σ2(Fo2) + (0.0478P)2] where P = (Fo2 + 2Fc2)/3 |
wR(F2) = 0.104 | (Δ/σ)max < 0.001 |
S = 0.99 | Δρmax = 0.23 e Å−3 |
1461 reflections | Δρmin = −0.24 e Å−3 |
139 parameters | Absolute structure: Refinement was carried out on a data set with averaged Friedel pairs,
therefore no _refine_ls_abs_structure_Flack is reported. |
Crystal data top
C12H20N2O | V = 1096.8 (2) Å3 |
Mr = 208.30 | Z = 4 |
Orthorhombic, P212121 | Mo Kα radiation |
a = 8.4691 (9) Å | µ = 0.08 mm−1 |
b = 10.3985 (8) Å | T = 150 K |
c = 12.4538 (15) Å | 0.3 × 0.2 × 0.1 mm |
Data collection top
Enraf Nonius CAD4T diffractometer | Rint = 0.035 |
2161 measured reflections | 3 standard reflections every 60 min |
1461 independent reflections | intensity decay: 6% |
1007 reflections with I > 2σ(I) | |
Refinement top
R[F2 > 2σ(F2)] = 0.050 | 0 restraints |
wR(F2) = 0.104 | H atoms treated by a mixture of independent and constrained refinement |
S = 0.99 | Δρmax = 0.23 e Å−3 |
1461 reflections | Δρmin = −0.24 e Å−3 |
139 parameters | Absolute structure: Refinement was carried out on a data set with averaged Friedel pairs,
therefore no _refine_ls_abs_structure_Flack is reported. |
Special details top
Geometry. Bond distances, angles etc. have been calculated using the rounded fractional coordinates. All e.s.d.'s are estimated from the variances of the (full) variance-covariance matrix. The cell e.s.d.'s are taken into account in the estimation of distances, angles and torsion angles |
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top | x | y | z | Uiso*/Ueq | |
O11 | 0.3058 (2) | 0.19551 (19) | 0.18233 (17) | 0.0249 (6) | |
N4 | 0.1897 (3) | −0.0947 (2) | 0.47817 (19) | 0.0237 (8) | |
N9A | 0.1409 (2) | −0.0094 (2) | 0.30581 (19) | 0.0216 (7) | |
C1 | 0.3008 (3) | −0.0194 (3) | 0.2635 (2) | 0.0197 (8) | |
C2 | 0.3912 (3) | −0.1123 (3) | 0.3345 (2) | 0.0235 (9) | |
C3 | 0.3595 (3) | −0.0865 (3) | 0.4528 (2) | 0.0250 (10) | |
C4A | 0.0978 (3) | −0.0569 (3) | 0.4033 (2) | 0.0203 (9) | |
C4B | −0.0812 (3) | −0.0614 (3) | 0.4064 (2) | 0.0238 (9) | |
C5 | −0.1563 (3) | −0.0402 (3) | 0.5159 (2) | 0.0281 (10) | |
C6 | −0.1511 (3) | 0.0989 (3) | 0.5528 (2) | 0.0284 (10) | |
C7 | −0.2219 (3) | 0.1869 (3) | 0.4678 (3) | 0.0304 (10) | |
C8 | −0.1279 (4) | 0.1745 (3) | 0.3639 (2) | 0.0270 (9) | |
C8A | −0.1266 (3) | 0.0378 (3) | 0.3208 (2) | 0.0227 (9) | |
C9 | 0.0042 (3) | 0.0202 (3) | 0.2380 (2) | 0.0250 (9) | |
C10 | 0.3804 (3) | 0.1115 (3) | 0.2555 (2) | 0.0243 (9) | |
H1 | 0.29470 | −0.05700 | 0.18970 | 0.0240* | |
H4B | −0.11500 | −0.14800 | 0.38000 | 0.0290* | |
H8A | −0.23140 | 0.01590 | 0.28880 | 0.0270* | |
H11 | 0.324 (3) | 0.161 (3) | 0.106 (2) | 0.0370* | |
H21 | 0.50570 | −0.10390 | 0.32020 | 0.0280* | |
H22 | 0.35950 | −0.20160 | 0.31700 | 0.0280* | |
H31 | 0.41800 | −0.14980 | 0.49680 | 0.0300* | |
H32 | 0.39890 | 0.00030 | 0.47150 | 0.0300* | |
H51 | −0.26770 | −0.06870 | 0.51320 | 0.0340* | |
H52 | −0.10100 | −0.09430 | 0.56950 | 0.0340* | |
H61 | −0.04030 | 0.12430 | 0.56670 | 0.0340* | |
H62 | −0.21090 | 0.10790 | 0.62070 | 0.0340* | |
H71 | −0.21920 | 0.27710 | 0.49310 | 0.0360* | |
H72 | −0.33340 | 0.16290 | 0.45470 | 0.0360* | |
H81 | −0.17410 | 0.23230 | 0.30910 | 0.0320* | |
H82 | −0.01790 | 0.20260 | 0.37700 | 0.0320* | |
H91 | −0.01970 | −0.05150 | 0.18830 | 0.0300* | |
H92 | 0.02140 | 0.09980 | 0.19600 | 0.0300* | |
H101 | 0.38120 | 0.15200 | 0.32750 | 0.0290* | |
H102 | 0.49160 | 0.09910 | 0.23310 | 0.0290* | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
O11 | 0.0276 (10) | 0.0226 (12) | 0.0244 (11) | −0.0015 (9) | −0.0019 (10) | 0.0031 (10) |
N4 | 0.0200 (12) | 0.0265 (14) | 0.0245 (13) | 0.0007 (11) | −0.0011 (11) | 0.0029 (13) |
N9A | 0.0146 (10) | 0.0274 (14) | 0.0228 (13) | 0.0039 (11) | −0.0014 (10) | 0.0019 (11) |
C1 | 0.0166 (13) | 0.0220 (15) | 0.0204 (15) | 0.0021 (12) | −0.0004 (12) | −0.0025 (14) |
C2 | 0.0201 (14) | 0.0244 (16) | 0.0259 (16) | 0.0039 (13) | −0.0009 (13) | 0.0000 (14) |
C3 | 0.0205 (14) | 0.0274 (19) | 0.0272 (17) | 0.0014 (14) | −0.0062 (13) | 0.0052 (15) |
C4A | 0.0211 (15) | 0.0150 (14) | 0.0247 (16) | 0.0017 (13) | 0.0019 (13) | 0.0017 (14) |
C4B | 0.0216 (15) | 0.0219 (16) | 0.0278 (17) | −0.0053 (13) | −0.0008 (13) | 0.0003 (15) |
C5 | 0.0210 (14) | 0.0331 (18) | 0.0302 (18) | −0.0042 (14) | 0.0021 (13) | 0.0074 (16) |
C6 | 0.0252 (15) | 0.0349 (19) | 0.0251 (16) | −0.0010 (15) | 0.0048 (13) | −0.0044 (15) |
C7 | 0.0295 (16) | 0.0270 (18) | 0.0348 (18) | 0.0048 (15) | −0.0027 (15) | −0.0039 (17) |
C8 | 0.0309 (16) | 0.0214 (16) | 0.0287 (17) | 0.0052 (15) | −0.0043 (14) | 0.0045 (14) |
C8A | 0.0143 (13) | 0.0285 (17) | 0.0253 (15) | −0.0024 (13) | −0.0049 (14) | −0.0017 (15) |
C9 | 0.0218 (13) | 0.0295 (17) | 0.0238 (15) | 0.0020 (14) | −0.0079 (13) | 0.0005 (15) |
C10 | 0.0219 (14) | 0.0269 (16) | 0.0240 (16) | 0.0000 (14) | −0.0023 (13) | 0.0014 (15) |
Geometric parameters (Å, º) top
O11—C10 | 1.412 (3) | C2—H21 | 0.9898 |
O11—H11 | 1.03 (3) | C2—H22 | 0.9909 |
N4—C3 | 1.475 (4) | C3—H31 | 0.9894 |
N4—C4A | 1.277 (4) | C3—H32 | 0.9901 |
N9A—C4A | 1.361 (3) | C4B—H4B | 1.0005 |
N9A—C9 | 1.466 (3) | C5—H51 | 0.9895 |
N9A—C1 | 1.457 (3) | C5—H52 | 0.9907 |
C1—C2 | 1.517 (4) | C6—H61 | 0.9901 |
C1—C10 | 1.522 (4) | C6—H62 | 0.9901 |
C2—C3 | 1.521 (4) | C7—H71 | 0.9897 |
C4A—C4B | 1.517 (4) | C7—H72 | 0.9903 |
C4B—C8A | 1.532 (4) | C8—H81 | 0.9900 |
C4B—C5 | 1.521 (4) | C8—H82 | 0.9899 |
C5—C6 | 1.518 (4) | C8A—H8A | 0.9992 |
C6—C7 | 1.522 (4) | C9—H91 | 0.9899 |
C7—C8 | 1.525 (4) | C9—H92 | 0.9899 |
C8—C8A | 1.519 (4) | C10—H101 | 0.9907 |
C8A—C9 | 1.524 (4) | C10—H102 | 0.9906 |
C1—H1 | 1.0001 | | |
| | | |
O11···N9A | 2.976 (3) | H22···C4A | 2.8864 |
O11···C9 | 3.214 (3) | H22···H52xi | 2.5718 |
O11···C2i | 3.259 (3) | H22···C10v | 3.0732 |
O11···N4ii | 2.750 (3) | H22···H81vi | 2.3247 |
O11···C3ii | 3.379 (3) | H22···H102v | 2.5049 |
O11···C4Biii | 3.351 (3) | H31···H11iv | 2.4624 |
O11···H92 | 2.6117 | H31···H92iv | 2.5861 |
O11···H4Biii | 2.4211 | H32···C10 | 2.9322 |
O11···H21i | 2.6268 | H32···H101 | 2.3931 |
N4···O11iv | 2.750 (3) | H32···H71xii | 2.5598 |
N9A···O11 | 2.976 (3) | H51···H72 | 2.5769 |
N4···H11iv | 1.74 (3) | H52···N4 | 2.7120 |
N4···H52 | 2.7120 | H52···C10iv | 2.9813 |
N9A···H82 | 2.7303 | H52···H11iv | 2.4882 |
C2···O11v | 3.259 (3) | H52···H102iv | 2.2388 |
C3···O11iv | 3.379 (3) | H52···H22xiii | 2.5718 |
C4B···O11vi | 3.351 (3) | H61···C4A | 3.0098 |
C9···O11 | 3.214 (3) | H61···H82 | 2.5060 |
C1···H81vi | 2.9386 | H62···H8Axiv | 2.5057 |
C2···H81vi | 3.0315 | H62···H91xiv | 2.5017 |
C3···H11iv | 2.58 (3) | H71···H32vii | 2.5598 |
C3···H101 | 2.9359 | H71···H101vii | 2.5017 |
C4A···H82 | 2.8894 | H72···H51 | 2.5769 |
C4A···H22 | 2.8864 | H81···H92 | 2.5736 |
C4A···H61 | 3.0098 | H81···C1iii | 2.9386 |
C4A···H11iv | 2.83 (3) | H81···C2iii | 3.0315 |
C6···H101vii | 3.0011 | H81···H1iii | 2.4174 |
C10···H32 | 2.9322 | H81···H22iii | 2.3247 |
C10···H52ii | 2.9813 | H82···N9A | 2.7303 |
C10···H22i | 3.0732 | H82···C4A | 2.8894 |
H1···H11 | 2.5074 | H82···H61 | 2.5060 |
H1···H81vi | 2.4174 | H82···H92 | 2.5169 |
H4B···O11vi | 2.4211 | H91···H62ix | 2.5017 |
H8A···H21viii | 2.5811 | H92···O11 | 2.6117 |
H8A···H102viii | 2.5948 | H92···H81 | 2.5736 |
H8A···H62ix | 2.5057 | H92···H82 | 2.5169 |
H11···H1 | 2.5074 | H92···H31ii | 2.5861 |
H11···N4ii | 1.74 (3) | H101···C3 | 2.9359 |
H11···C3ii | 2.58 (3) | H101···H32 | 2.3931 |
H11···C4Aii | 2.83 (3) | H101···C6xii | 3.0011 |
H11···H31ii | 2.4624 | H101···H71xii | 2.5017 |
H11···H52ii | 2.4882 | H102···H8Ax | 2.5948 |
H21···H8Ax | 2.5811 | H102···H21 | 2.3763 |
H21···H102 | 2.3763 | H102···H52ii | 2.2388 |
H21···O11v | 2.6268 | H102···H22i | 2.5049 |
| | | |
C10—O11—H11 | 108.3 (16) | H31—C3—H32 | 107.90 |
C3—N4—C4A | 114.8 (2) | C4A—C4B—H4B | 107.78 |
C1—N9A—C4A | 123.1 (2) | C5—C4B—H4B | 107.79 |
C4A—N9A—C9 | 112.24 (19) | C8A—C4B—H4B | 107.79 |
C1—N9A—C9 | 122.7 (2) | C4B—C5—H51 | 108.96 |
N9A—C1—C2 | 107.7 (2) | C4B—C5—H52 | 108.92 |
N9A—C1—C10 | 111.8 (2) | C6—C5—H51 | 108.86 |
C2—C1—C10 | 112.6 (2) | C6—C5—H52 | 108.86 |
C1—C2—C3 | 111.3 (2) | H51—C5—H52 | 107.67 |
N4—C3—C2 | 111.7 (2) | C5—C6—H61 | 109.54 |
N4—C4A—C4B | 125.5 (2) | C5—C6—H62 | 109.49 |
N9A—C4A—C4B | 107.6 (2) | C7—C6—H61 | 109.54 |
N4—C4A—N9A | 126.9 (2) | C7—C6—H62 | 109.61 |
C4A—C4B—C5 | 115.9 (2) | H61—C6—H62 | 108.07 |
C4A—C4B—C8A | 102.3 (2) | C6—C7—H71 | 109.83 |
C5—C4B—C8A | 114.9 (2) | C6—C7—H72 | 109.80 |
C4B—C5—C6 | 113.4 (2) | C8—C7—H71 | 109.77 |
C5—C6—C7 | 110.5 (2) | C8—C7—H72 | 109.68 |
C6—C7—C8 | 109.5 (2) | H71—C7—H72 | 108.26 |
C7—C8—C8A | 112.5 (2) | C7—C8—H81 | 109.11 |
C4B—C8A—C8 | 112.7 (2) | C7—C8—H82 | 109.06 |
C4B—C8A—C9 | 102.0 (2) | C8A—C8—H81 | 109.10 |
C8—C8A—C9 | 110.9 (2) | C8A—C8—H82 | 109.12 |
N9A—C9—C8A | 102.1 (2) | H81—C8—H82 | 107.84 |
O11—C10—C1 | 113.4 (2) | C4B—C8A—H8A | 110.30 |
N9A—C1—H1 | 108.20 | C8—C8A—H8A | 110.34 |
C2—C1—H1 | 108.23 | C9—C8A—H8A | 110.38 |
C10—C1—H1 | 108.20 | N9A—C9—H91 | 111.32 |
C1—C2—H21 | 109.47 | N9A—C9—H92 | 111.33 |
C1—C2—H22 | 109.38 | C8A—C9—H91 | 111.39 |
C3—C2—H21 | 109.36 | C8A—C9—H92 | 111.34 |
C3—C2—H22 | 109.30 | H91—C9—H92 | 109.24 |
H21—C2—H22 | 107.97 | O11—C10—H101 | 108.92 |
N4—C3—H31 | 109.34 | O11—C10—H102 | 108.92 |
N4—C3—H32 | 109.33 | C1—C10—H101 | 108.90 |
C2—C3—H31 | 109.31 | C1—C10—H102 | 108.85 |
C2—C3—H32 | 109.21 | H101—C10—H102 | 107.68 |
| | | |
C4A—N4—C3—C2 | −33.8 (3) | N4—C4A—C4B—C5 | 33.8 (4) |
C3—N4—C4A—N9A | −1.0 (4) | N4—C4A—C4B—C8A | 159.5 (3) |
C3—N4—C4A—C4B | 176.8 (3) | N9A—C4A—C4B—C5 | −148.1 (3) |
C4A—N9A—C1—C2 | 11.6 (3) | N9A—C4A—C4B—C8A | −22.3 (3) |
C1—N9A—C4A—N4 | 13.3 (5) | C8A—C4B—C5—C6 | −44.8 (3) |
C1—N9A—C4A—C4B | −164.9 (2) | C5—C4B—C8A—C8 | 42.4 (3) |
C9—N9A—C4A—N4 | 177.9 (3) | C4A—C4B—C8A—C8 | −84.0 (3) |
C9—N9A—C4A—C4B | −0.3 (3) | C4A—C4B—C8A—C9 | 34.9 (3) |
C1—N9A—C9—C8A | −172.5 (2) | C4A—C4B—C5—C6 | 74.3 (3) |
C4A—N9A—C9—C8A | 22.8 (3) | C5—C4B—C8A—C9 | 161.3 (2) |
C4A—N9A—C1—C10 | −112.6 (3) | C4B—C5—C6—C7 | 53.5 (3) |
C9—N9A—C1—C2 | −151.5 (2) | C5—C6—C7—C8 | −60.2 (3) |
C9—N9A—C1—C10 | 84.4 (3) | C6—C7—C8—C8A | 59.1 (3) |
C2—C1—C10—O11 | 174.7 (2) | C7—C8—C8A—C9 | −163.4 (2) |
N9A—C1—C10—O11 | −63.9 (3) | C7—C8—C8A—C4B | −49.8 (3) |
N9A—C1—C2—C3 | −44.1 (3) | C4B—C8A—C9—N9A | −35.0 (3) |
C10—C1—C2—C3 | 79.6 (3) | C8—C8A—C9—N9A | 85.2 (3) |
C1—C2—C3—N4 | 57.6 (3) | | |
Symmetry codes: (i) −x+1, y+1/2, −z+1/2; (ii) −x+1/2, −y, z−1/2; (iii) −x, y+1/2, −z+1/2; (iv) −x+1/2, −y, z+1/2; (v) −x+1, y−1/2, −z+1/2; (vi) −x, y−1/2, −z+1/2; (vii) x−1/2, −y+1/2, −z+1; (viii) x−1, y, z; (ix) −x−1/2, −y, z−1/2; (x) x+1, y, z; (xi) x+1/2, −y−1/2, −z+1; (xii) x+1/2, −y+1/2, −z+1; (xiii) x−1/2, −y−1/2, −z+1; (xiv) −x−1/2, −y, z+1/2. |
Hydrogen-bond geometry (Å, º) top
D—H···A | D—H | H···A | D···A | D—H···A |
O11—H11···N4ii | 1.03 (3) | 1.74 (3) | 2.750 (3) | 167 (2) |
C4B—H4B···O11vi | 1.0005 | 2.4211 | 3.351 (3) | 154.33 |
Symmetry codes: (ii) −x+1/2, −y, z−1/2; (vi) −x, y−1/2, −z+1/2. |
Experimental details
Crystal data |
Chemical formula | C12H20N2O |
Mr | 208.30 |
Crystal system, space group | Orthorhombic, P212121 |
Temperature (K) | 150 |
a, b, c (Å) | 8.4691 (9), 10.3985 (8), 12.4538 (15) |
V (Å3) | 1096.8 (2) |
Z | 4 |
Radiation type | Mo Kα |
µ (mm−1) | 0.08 |
Crystal size (mm) | 0.3 × 0.2 × 0.1 |
|
Data collection |
Diffractometer | Enraf Nonius CAD4T diffractometer |
Absorption correction | – |
No. of measured, independent and observed [I > 2σ(I)] reflections | 2161, 1461, 1007 |
Rint | 0.035 |
(sin θ/λ)max (Å−1) | 0.649 |
|
Refinement |
R[F2 > 2σ(F2)], wR(F2), S | 0.050, 0.104, 0.99 |
No. of reflections | 1461 |
No. of parameters | 139 |
H-atom treatment | H atoms treated by a mixture of independent and constrained refinement |
Δρmax, Δρmin (e Å−3) | 0.23, −0.24 |
Absolute structure | Refinement was carried out on a data set with averaged Friedel pairs,
therefore no _refine_ls_abs_structure_Flack is reported. |
Selected geometric parameters (Å, º) topO11—C10 | 1.412 (3) | N9A—C4A | 1.361 (3) |
N4—C3 | 1.475 (4) | N9A—C9 | 1.466 (3) |
N4—C4A | 1.277 (4) | N9A—C1 | 1.457 (3) |
| | | |
C3—N4—C4A | 114.8 (2) | C4A—N9A—C9 | 112.24 (19) |
C1—N9A—C4A | 123.1 (2) | C1—N9A—C9 | 122.7 (2) |
Hydrogen-bond geometry (Å, º) top
D—H···A | D—H | H···A | D···A | D—H···A |
O11—H11···N4i | 1.03 (3) | 1.74 (3) | 2.750 (3) | 167 (2) |
C4B—H4B···O11ii | 1.0005 | 2.4211 | 3.351 (3) | 154.33 |
Symmetry codes: (i) −x+1/2, −y, z−1/2; (ii) −x, y−1/2, −z+1/2. |
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The title compound was prepared during a study on the synthesis of enantiopure hydroxyamidines (Ostendorf et al., 2000). The crystal structure determination was undertaken in order to establish the configuration of atoms C4b and C8a (note crystallographic numbering) with respect to the known (R) configuration of C4. C4b turned out to have the S configuration, while C8a has the R configuration.
Due to the presence of the double-bond C3═N4 and the sp2 hybridization of N9a, the atoms of the nitrogen-containing rings more or less lie within one plane [maximum deviation from the least-squares plane is 0.118 (3) Å for C1], with the exception of atoms C2 [deviation 0.695 (3) Å] and C8a [deviation 0.515 (3) Å] which protrude on opposite sides. The five-membered ring and the six-membered heteroatomic ring are therefore in a somewhat distorted envelope conformation. The six-membered carbon ring has adopted a slightly deformed chair conformation.
The hydroxyl group donates an intermolecular hydrogen bond to N4 (geometric details in Table 2), thus forming an infinite one-dimensional chain parallel to the c axis [graph set C(7); Bernstein et al., 1995]. The two screw-related anti-parallel chains present in the unit cell are joined by C—H···O interactions involving C4a and O11 (geometric details in Table 2), creating a two-dimensional network perpendicular to the a axis. The C—H···O interactions by themselves organize the molecules in infinite one-dimensional chains [graph set C(7)] parallel to the b axis.