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The title compound, C
16H
16N
2O
2, was prepared by reaction of 2-aminophenol and diacetyl. A colorless crystal was obtained by recrystallization from an MeOH–H
2O solution. X-ray analysis reveals that the molecule has no crystallographically imposed symmetry. The heterocyclic rings adopt opposite twist conformations, leading to an overall V-shaped twist conformation. Weak intermolecular N—H
O hydrogen-bonding interactions link the molecules into a one-dimensional chain along the
c axis.
Supporting information
CCDC reference: 251750
Key indicators
- Single-crystal X-ray study
- T = 293 K
- Mean (C-C) = 0.005 Å
- R factor = 0.077
- wR factor = 0.220
- Data-to-parameter ratio = 13.2
checkCIF/PLATON results
No syntax errors found
Alert level A
PLAT707_ALERT_1_A D...A Calc 8.246(6), Rep 3.122(4), Dev.. 854.00 Sigma
N1 -O2 1.555 2.555
PLAT707_ALERT_1_A D...A Calc 17.593(12), Rep 3.117(3), Dev.. 1206.33 Sigma
N2 -O1 1.555 2.565
PLAT726_ALERT_1_A H...A Calc 9.08778, Rep 2.55000 Dev... 6.54 Ang.
H1 -O2 1.555 2.555
PLAT726_ALERT_1_A H...A Calc 17.15500, Rep 2.54000 Dev... 14.62 Ang.
H2 -O1 1.555 2.565
PLAT728_ALERT_1_A D-H..A Calc 11.45, Rep 125.00 Dev... 113.55 Deg.
N1 -H1 -O2 1.555 1.555 2.555
PLAT728_ALERT_1_A D-H..A Calc 119.37, Rep 126.00 Dev... 6.63 Deg.
N2 -H2 -O1 1.555 1.555 2.565
Alert level C
DIFMX01_ALERT_2_C The maximum difference density is > 0.1*ZMAX*0.75
_refine_diff_density_max given = 0.720
Test value = 0.600
DIFMX02_ALERT_1_C The minimum difference density is > 0.1*ZMAX*0.75
The relevant atom site should be identified.
PLAT029_ALERT_3_C _diffrn_measured_fraction_theta_full Low ....... 0.98
PLAT094_ALERT_2_C Ratio of Maximum / Minimum Residual Density .... 2.57
PLAT097_ALERT_2_C Maximum (Positive) Residual Density ............ 0.72 e/A 3
PLAT125_ALERT_4_C No _symmetry_space_group_name_Hall Given ....... ?
PLAT340_ALERT_3_C Low Bond Precision on C-C bonds (x 1000) Ang ... 5
PLAT737_ALERT_1_C D...A Calc 17.593(12), Rep 3.117(3) ...... 4.00 su-Rat
N2 -O1 1.555 2.565
6 ALERT level A = In general: serious problem
0 ALERT level B = Potentially serious problem
8 ALERT level C = Check and explain
0 ALERT level G = General alerts; check
8 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
3 ALERT type 2 Indicator that the structure model may be wrong or deficient
2 ALERT type 3 Indicator that the structure quality may be low
1 ALERT type 4 Improvement, methodology, query or suggestion
Data collection: SMART (Bruker, 1998); cell refinement: SMART; data reduction: SAINT (Bruker, 1998); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: SHELXTL (Bruker, 1998); software used to prepare material for publication: SHELXTL.
5a,6,11
a,12-Tetrahydro-5a,11
a-dimethyl-1,4-benzoxazino[3,2-
b][1,4]benzoxazine
top
Crystal data top
C16H16N2O2 | F(000) = 568 |
Mr = 268.31 | Dx = 1.279 Mg m−3 |
Monoclinic, P21/c | Mo Kα radiation, λ = 0.71073 Å |
a = 11.025 (7) Å | Cell parameters from 739 reflections |
b = 11.238 (7) Å | θ = 3.6–25.1° |
c = 11.666 (7) Å | µ = 0.09 mm−1 |
β = 105.484 (10)° | T = 293 K |
V = 1392.9 (15) Å3 | Block, colorless |
Z = 4 | 0.20 × 0.18 × 0.14 mm |
Data collection top
Bruker SMART CCD area-detector diffractometer | 1621 reflections with I > 2σ(I) |
Radiation source: fine-focus sealed tube | Rint = 0.033 |
Graphite monochromator | θmax = 25.0°, θmin = 2.6° |
φ and ω scans | h = −13→11 |
6838 measured reflections | k = −13→12 |
2408 independent reflections | l = −13→13 |
Refinement top
Refinement on F2 | Primary atom site location: structure-invariant direct methods |
Least-squares matrix: full | Secondary atom site location: difference Fourier map |
R[F2 > 2σ(F2)] = 0.077 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.220 | H atoms treated by a mixture of independent and constrained refinement |
S = 1.01 | w = 1/[σ2(Fo2) + (0.1574P)2] where P = (Fo2 + 2Fc2)/3 |
2408 reflections | (Δ/σ)max < 0.001 |
183 parameters | Δρmax = 0.72 e Å−3 |
0 restraints | Δρmin = −0.28 e Å−3 |
Special details top
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 (Å2) top | x | y | z | Uiso*/Ueq | |
N1 | 0.1128 (2) | 0.1267 (2) | −0.01817 (19) | 0.0413 (6) | |
H1 | 0.1316 | 0.0678 | −0.0573 | 0.050* | |
N2 | −0.1104 (2) | 0.3731 (2) | −0.07434 (19) | 0.0408 (6) | |
H2 | −0.1294 | 0.4320 | −0.1229 | 0.049* | |
O1 | 0.07866 (17) | 0.35124 (16) | 0.07054 (15) | 0.0387 (5) | |
O2 | −0.07529 (17) | 0.14876 (16) | 0.03206 (15) | 0.0388 (5) | |
C1 | 0.0814 (3) | 0.3645 (3) | −0.1363 (2) | 0.0478 (8) | |
H1A | 0.0379 | 0.3435 | −0.2165 | 0.072* | |
H1B | 0.1639 | 0.3295 | −0.1160 | 0.072* | |
H1C | 0.0888 | 0.4495 | −0.1296 | 0.072* | |
C2 | 0.0080 (2) | 0.3184 (2) | −0.0519 (2) | 0.0340 (6) | |
C3 | −0.0062 (2) | 0.1821 (2) | −0.0556 (2) | 0.0331 (6) | |
C4 | −0.0799 (3) | 0.1349 (3) | −0.1765 (2) | 0.0468 (7) | |
H4A | −0.0354 | 0.1532 | −0.2347 | 0.070* | |
H4B | −0.1615 | 0.1716 | −0.1990 | 0.070* | |
H4C | −0.0894 | 0.0503 | −0.1721 | 0.070* | |
C5 | 0.1835 (3) | 0.2830 (3) | 0.1243 (2) | 0.0400 (7) | |
C6 | 0.1992 (3) | 0.1697 (3) | 0.0839 (2) | 0.0415 (7) | |
C7 | 0.3032 (3) | 0.1039 (3) | 0.1445 (3) | 0.0551 (8) | |
H7 | 0.3157 | 0.0280 | 0.1180 | 0.066* | |
C8 | 0.3886 (3) | 0.1502 (4) | 0.2441 (3) | 0.0663 (10) | |
H8 | 0.4575 | 0.1049 | 0.2843 | 0.080* | |
C9 | 0.3720 (3) | 0.2617 (4) | 0.2833 (3) | 0.0647 (10) | |
H9 | 0.4294 | 0.2922 | 0.3503 | 0.078* | |
C10 | 0.2679 (3) | 0.3308 (3) | 0.2225 (3) | 0.0533 (8) | |
H10 | 0.2565 | 0.4073 | 0.2482 | 0.064* | |
C11 | −0.1801 (2) | 0.2168 (2) | 0.0331 (2) | 0.0385 (7) | |
C12 | −0.1962 (3) | 0.3301 (2) | −0.0166 (2) | 0.0405 (7) | |
C13 | −0.3010 (3) | 0.3956 (3) | −0.0081 (3) | 0.0547 (8) | |
H13 | −0.3143 | 0.4713 | −0.0412 | 0.066* | |
C14 | −0.3851 (3) | 0.3493 (4) | 0.0487 (4) | 0.0690 (11) | |
H14 | −0.4541 | 0.3943 | 0.0540 | 0.083* | |
C15 | −0.3680 (3) | 0.2373 (4) | 0.0977 (3) | 0.0660 (10) | |
H15 | −0.4247 | 0.2067 | 0.1365 | 0.079* | |
C16 | −0.2645 (3) | 0.1700 (3) | 0.0885 (3) | 0.0531 (8) | |
H16 | −0.2528 | 0.0935 | 0.1200 | 0.064* | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
N1 | 0.0559 (14) | 0.0276 (12) | 0.0438 (13) | 0.0066 (10) | 0.0193 (11) | −0.0028 (9) |
N2 | 0.0552 (15) | 0.0278 (12) | 0.0376 (12) | 0.0058 (10) | 0.0094 (11) | 0.0058 (9) |
O1 | 0.0499 (11) | 0.0305 (11) | 0.0342 (10) | −0.0005 (8) | 0.0085 (8) | −0.0038 (7) |
O2 | 0.0517 (12) | 0.0298 (10) | 0.0382 (10) | 0.0018 (8) | 0.0176 (9) | 0.0044 (7) |
C1 | 0.071 (2) | 0.0376 (16) | 0.0392 (15) | −0.0055 (14) | 0.0227 (14) | 0.0050 (12) |
C2 | 0.0524 (16) | 0.0238 (13) | 0.0270 (12) | −0.0025 (11) | 0.0127 (11) | −0.0005 (9) |
C3 | 0.0500 (15) | 0.0230 (13) | 0.0281 (12) | −0.0013 (11) | 0.0136 (11) | 0.0008 (9) |
C4 | 0.0676 (19) | 0.0353 (16) | 0.0371 (15) | −0.0037 (14) | 0.0133 (13) | −0.0063 (11) |
C5 | 0.0443 (15) | 0.0415 (16) | 0.0364 (14) | −0.0021 (13) | 0.0145 (12) | 0.0042 (11) |
C6 | 0.0410 (15) | 0.0418 (16) | 0.0446 (16) | −0.0014 (12) | 0.0166 (13) | 0.0080 (12) |
C7 | 0.0500 (18) | 0.0512 (19) | 0.068 (2) | 0.0074 (15) | 0.0219 (16) | 0.0125 (15) |
C8 | 0.0434 (18) | 0.075 (3) | 0.076 (2) | 0.0050 (16) | 0.0069 (17) | 0.0207 (19) |
C9 | 0.0495 (19) | 0.083 (3) | 0.053 (2) | −0.0090 (18) | −0.0012 (15) | 0.0118 (17) |
C10 | 0.0547 (19) | 0.054 (2) | 0.0483 (18) | −0.0109 (15) | 0.0084 (15) | −0.0020 (14) |
C11 | 0.0421 (15) | 0.0399 (15) | 0.0326 (13) | −0.0020 (12) | 0.0085 (11) | −0.0033 (11) |
C12 | 0.0414 (15) | 0.0391 (16) | 0.0369 (14) | −0.0018 (12) | 0.0034 (12) | −0.0079 (11) |
C13 | 0.0467 (17) | 0.0474 (19) | 0.063 (2) | 0.0057 (14) | 0.0028 (15) | −0.0044 (14) |
C14 | 0.0468 (19) | 0.075 (3) | 0.087 (3) | 0.0066 (17) | 0.0210 (18) | −0.013 (2) |
C15 | 0.052 (2) | 0.084 (3) | 0.069 (2) | −0.0087 (18) | 0.0285 (17) | −0.0101 (19) |
C16 | 0.0581 (19) | 0.0512 (19) | 0.0536 (18) | −0.0060 (15) | 0.0210 (15) | −0.0004 (14) |
Geometric parameters (Å, º) top
N1—C6 | 1.398 (4) | C5—C6 | 1.384 (4) |
N1—C3 | 1.412 (3) | C6—C7 | 1.388 (4) |
N1—H1 | 0.8600 | C7—C8 | 1.386 (5) |
N2—C12 | 1.387 (4) | C7—H7 | 0.9300 |
N2—C2 | 1.402 (3) | C8—C9 | 1.363 (5) |
N2—H2 | 0.8600 | C8—H8 | 0.9300 |
O1—C5 | 1.390 (3) | C9—C10 | 1.410 (4) |
O1—C2 | 1.480 (3) | C9—H9 | 0.9300 |
O2—C11 | 1.388 (3) | C10—H10 | 0.9300 |
O2—C3 | 1.477 (3) | C11—C16 | 1.372 (4) |
C1—C2 | 1.522 (4) | C11—C12 | 1.390 (4) |
C1—H1A | 0.9600 | C12—C13 | 1.395 (4) |
C1—H1B | 0.9600 | C13—C14 | 1.377 (5) |
C1—H1C | 0.9600 | C13—H13 | 0.9300 |
C2—C3 | 1.540 (4) | C14—C15 | 1.374 (6) |
C3—C4 | 1.523 (4) | C14—H14 | 0.9300 |
C4—H4A | 0.9600 | C15—C16 | 1.397 (4) |
C4—H4B | 0.9600 | C15—H15 | 0.9300 |
C4—H4C | 0.9600 | C16—H16 | 0.9300 |
C5—C10 | 1.377 (4) | | |
| | | |
C6—N1—C3 | 118.5 (2) | C6—C5—O1 | 121.2 (2) |
C6—N1—H1 | 120.8 | C5—C6—C7 | 118.5 (3) |
C3—N1—H1 | 120.8 | C5—C6—N1 | 119.3 (2) |
C12—N2—C2 | 118.6 (2) | C7—C6—N1 | 122.2 (3) |
C12—N2—H2 | 120.7 | C8—C7—C6 | 120.7 (3) |
C2—N2—H2 | 120.7 | C8—C7—H7 | 119.6 |
C5—O1—C2 | 117.3 (2) | C6—C7—H7 | 119.6 |
C11—O2—C3 | 116.8 (2) | C9—C8—C7 | 120.2 (3) |
C2—C1—H1A | 109.5 | C9—C8—H8 | 119.9 |
C2—C1—H1B | 109.5 | C7—C8—H8 | 119.9 |
H1A—C1—H1B | 109.5 | C8—C9—C10 | 120.1 (3) |
C2—C1—H1C | 109.5 | C8—C9—H9 | 119.9 |
H1A—C1—H1C | 109.5 | C10—C9—H9 | 119.9 |
H1B—C1—H1C | 109.5 | C5—C10—C9 | 118.8 (3) |
N2—C2—O1 | 107.15 (19) | C5—C10—H10 | 120.6 |
N2—C2—C1 | 111.1 (2) | C9—C10—H10 | 120.6 |
O1—C2—C1 | 107.8 (2) | C16—C11—O2 | 117.6 (3) |
N2—C2—C3 | 110.4 (2) | C16—C11—C12 | 121.4 (3) |
O1—C2—C3 | 107.34 (18) | O2—C11—C12 | 121.0 (2) |
C1—C2—C3 | 112.8 (2) | N2—C12—C11 | 119.6 (2) |
N1—C3—O2 | 106.42 (19) | N2—C12—C13 | 122.4 (3) |
N1—C3—C4 | 110.8 (2) | C11—C12—C13 | 118.0 (3) |
O2—C3—C4 | 107.9 (2) | C14—C13—C12 | 120.7 (3) |
N1—C3—C2 | 110.5 (2) | C14—C13—H13 | 119.6 |
O2—C3—C2 | 107.48 (19) | C12—C13—H13 | 119.6 |
C4—C3—C2 | 113.4 (2) | C15—C14—C13 | 120.7 (3) |
C3—C4—H4A | 109.5 | C15—C14—H14 | 119.6 |
C3—C4—H4B | 109.5 | C13—C14—H14 | 119.6 |
H4A—C4—H4B | 109.5 | C14—C15—C16 | 119.2 (3) |
C3—C4—H4C | 109.5 | C14—C15—H15 | 120.4 |
H4A—C4—H4C | 109.5 | C16—C15—H15 | 120.4 |
H4B—C4—H4C | 109.5 | C11—C16—C15 | 119.9 (3) |
C10—C5—C6 | 121.6 (3) | C11—C16—H16 | 120.0 |
C10—C5—O1 | 117.1 (3) | C15—C16—H16 | 120.0 |
| | | |
C12—N2—C2—O1 | −71.1 (3) | O1—C5—C6—N1 | 4.7 (4) |
C12—N2—C2—C1 | 171.4 (2) | C3—N1—C6—C5 | −19.2 (4) |
C12—N2—C2—C3 | 45.5 (3) | C3—N1—C6—C7 | 162.8 (2) |
C5—O1—C2—N2 | 162.8 (2) | C5—C6—C7—C8 | 0.7 (4) |
C5—O1—C2—C1 | −77.5 (3) | N1—C6—C7—C8 | 178.7 (3) |
C5—O1—C2—C3 | 44.3 (3) | C6—C7—C8—C9 | −0.5 (5) |
C6—N1—C3—O2 | −70.9 (3) | C7—C8—C9—C10 | −0.2 (5) |
C6—N1—C3—C4 | 172.1 (2) | C6—C5—C10—C9 | −0.5 (4) |
C6—N1—C3—C2 | 45.5 (3) | O1—C5—C10—C9 | 176.7 (2) |
C11—O2—C3—N1 | 163.1 (2) | C8—C9—C10—C5 | 0.7 (5) |
C11—O2—C3—C4 | −77.9 (3) | C3—O2—C11—C16 | 162.5 (2) |
C11—O2—C3—C2 | 44.7 (3) | C3—O2—C11—C12 | −19.7 (3) |
N2—C2—C3—N1 | −172.47 (18) | C2—N2—C12—C11 | −18.5 (4) |
O1—C2—C3—N1 | −56.0 (3) | C2—N2—C12—C13 | 162.8 (2) |
C1—C2—C3—N1 | 62.6 (3) | C16—C11—C12—N2 | −178.4 (3) |
N2—C2—C3—O2 | −56.7 (2) | O2—C11—C12—N2 | 3.9 (4) |
O1—C2—C3—O2 | 59.7 (3) | C16—C11—C12—C13 | 0.3 (4) |
C1—C2—C3—O2 | 178.3 (2) | O2—C11—C12—C13 | −177.4 (2) |
N2—C2—C3—C4 | 62.4 (3) | N2—C12—C13—C14 | 179.2 (3) |
O1—C2—C3—C4 | 178.9 (2) | C11—C12—C13—C14 | 0.5 (4) |
C1—C2—C3—C4 | −62.5 (3) | C12—C13—C14—C15 | −0.4 (5) |
C2—O1—C5—C10 | 162.8 (2) | C13—C14—C15—C16 | −0.5 (6) |
C2—O1—C5—C6 | −20.0 (3) | O2—C11—C16—C15 | 176.6 (2) |
C10—C5—C6—C7 | −0.2 (4) | C12—C11—C16—C15 | −1.1 (4) |
O1—C5—C6—C7 | −177.2 (2) | C14—C15—C16—C11 | 1.3 (5) |
C10—C5—C6—N1 | −178.2 (3) | | |
Hydrogen-bond geometry (Å, º) top
D—H···A | D—H | H···A | D···A | D—H···A |
N1—H1···O2i | 0.86 | 2.55 | 3.122 (4) | 125 |
N2—H2···O1ii | 0.86 | 2.54 | 3.117 (3) | 126 |
Symmetry codes: (i) −x, y+1/2, −z+1/2; (ii) −x, y+3/2, −z+1/2. |
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