Buy article online - an online subscription or single-article purchase is required to access this article.
Download citation
Download citation
link to html
The title compound, C16H16N2O2, was prepared by reaction of 2-amino­phenol and di­acetyl. A colorless crystal was obtained by recrystallization from an MeOH–H2O 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

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536804020665/cv6360sup1.cif
Contains datablocks global, I

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536804020665/cv6360Isup2.hkl
Contains datablock I

CCDC reference: 251750

Key indicators

  • Single-crystal X-ray study
  • T = 293 K
  • Mean [sigma](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

Computing details top

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,6,11a,12-Tetrahydro-5a,11a-dimethyl-1,4-benzoxazino[3,2-b][1,4]benzoxazine top
Crystal data top
C16H16N2O2F(000) = 568
Mr = 268.31Dx = 1.279 Mg m3
Monoclinic, P21/cMo Kα radiation, λ = 0.71073 Å
a = 11.025 (7) ÅCell parameters from 739 reflections
b = 11.238 (7) Åθ = 3.6–25.1°
c = 11.666 (7) ŵ = 0.09 mm1
β = 105.484 (10)°T = 293 K
V = 1392.9 (15) Å3Block, colorless
Z = 40.20 × 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 tubeRint = 0.033
Graphite monochromatorθmax = 25.0°, θmin = 2.6°
φ and ω scansh = 1311
6838 measured reflectionsk = 1312
2408 independent reflectionsl = 1313
Refinement top
Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.077Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.220H 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 parametersΔρmax = 0.72 e Å3
0 restraintsΔρmin = 0.28 e Å3
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
xyzUiso*/Ueq
N10.1128 (2)0.1267 (2)0.01817 (19)0.0413 (6)
H10.13160.06780.05730.050*
N20.1104 (2)0.3731 (2)0.07434 (19)0.0408 (6)
H20.12940.43200.12290.049*
O10.07866 (17)0.35124 (16)0.07054 (15)0.0387 (5)
O20.07529 (17)0.14876 (16)0.03206 (15)0.0388 (5)
C10.0814 (3)0.3645 (3)0.1363 (2)0.0478 (8)
H1A0.03790.34350.21650.072*
H1B0.16390.32950.11600.072*
H1C0.08880.44950.12960.072*
C20.0080 (2)0.3184 (2)0.0519 (2)0.0340 (6)
C30.0062 (2)0.1821 (2)0.0556 (2)0.0331 (6)
C40.0799 (3)0.1349 (3)0.1765 (2)0.0468 (7)
H4A0.03540.15320.23470.070*
H4B0.16150.17160.19900.070*
H4C0.08940.05030.17210.070*
C50.1835 (3)0.2830 (3)0.1243 (2)0.0400 (7)
C60.1992 (3)0.1697 (3)0.0839 (2)0.0415 (7)
C70.3032 (3)0.1039 (3)0.1445 (3)0.0551 (8)
H70.31570.02800.11800.066*
C80.3886 (3)0.1502 (4)0.2441 (3)0.0663 (10)
H80.45750.10490.28430.080*
C90.3720 (3)0.2617 (4)0.2833 (3)0.0647 (10)
H90.42940.29220.35030.078*
C100.2679 (3)0.3308 (3)0.2225 (3)0.0533 (8)
H100.25650.40730.24820.064*
C110.1801 (2)0.2168 (2)0.0331 (2)0.0385 (7)
C120.1962 (3)0.3301 (2)0.0166 (2)0.0405 (7)
C130.3010 (3)0.3956 (3)0.0081 (3)0.0547 (8)
H130.31430.47130.04120.066*
C140.3851 (3)0.3493 (4)0.0487 (4)0.0690 (11)
H140.45410.39430.05400.083*
C150.3680 (3)0.2373 (4)0.0977 (3)0.0660 (10)
H150.42470.20670.13650.079*
C160.2645 (3)0.1700 (3)0.0885 (3)0.0531 (8)
H160.25280.09350.12000.064*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
N10.0559 (14)0.0276 (12)0.0438 (13)0.0066 (10)0.0193 (11)0.0028 (9)
N20.0552 (15)0.0278 (12)0.0376 (12)0.0058 (10)0.0094 (11)0.0058 (9)
O10.0499 (11)0.0305 (11)0.0342 (10)0.0005 (8)0.0085 (8)0.0038 (7)
O20.0517 (12)0.0298 (10)0.0382 (10)0.0018 (8)0.0176 (9)0.0044 (7)
C10.071 (2)0.0376 (16)0.0392 (15)0.0055 (14)0.0227 (14)0.0050 (12)
C20.0524 (16)0.0238 (13)0.0270 (12)0.0025 (11)0.0127 (11)0.0005 (9)
C30.0500 (15)0.0230 (13)0.0281 (12)0.0013 (11)0.0136 (11)0.0008 (9)
C40.0676 (19)0.0353 (16)0.0371 (15)0.0037 (14)0.0133 (13)0.0063 (11)
C50.0443 (15)0.0415 (16)0.0364 (14)0.0021 (13)0.0145 (12)0.0042 (11)
C60.0410 (15)0.0418 (16)0.0446 (16)0.0014 (12)0.0166 (13)0.0080 (12)
C70.0500 (18)0.0512 (19)0.068 (2)0.0074 (15)0.0219 (16)0.0125 (15)
C80.0434 (18)0.075 (3)0.076 (2)0.0050 (16)0.0069 (17)0.0207 (19)
C90.0495 (19)0.083 (3)0.053 (2)0.0090 (18)0.0012 (15)0.0118 (17)
C100.0547 (19)0.054 (2)0.0483 (18)0.0109 (15)0.0084 (15)0.0020 (14)
C110.0421 (15)0.0399 (15)0.0326 (13)0.0020 (12)0.0085 (11)0.0033 (11)
C120.0414 (15)0.0391 (16)0.0369 (14)0.0018 (12)0.0034 (12)0.0079 (11)
C130.0467 (17)0.0474 (19)0.063 (2)0.0057 (14)0.0028 (15)0.0044 (14)
C140.0468 (19)0.075 (3)0.087 (3)0.0066 (17)0.0210 (18)0.013 (2)
C150.052 (2)0.084 (3)0.069 (2)0.0087 (18)0.0285 (17)0.0101 (19)
C160.0581 (19)0.0512 (19)0.0536 (18)0.0060 (15)0.0210 (15)0.0004 (14)
Geometric parameters (Å, º) top
N1—C61.398 (4)C5—C61.384 (4)
N1—C31.412 (3)C6—C71.388 (4)
N1—H10.8600C7—C81.386 (5)
N2—C121.387 (4)C7—H70.9300
N2—C21.402 (3)C8—C91.363 (5)
N2—H20.8600C8—H80.9300
O1—C51.390 (3)C9—C101.410 (4)
O1—C21.480 (3)C9—H90.9300
O2—C111.388 (3)C10—H100.9300
O2—C31.477 (3)C11—C161.372 (4)
C1—C21.522 (4)C11—C121.390 (4)
C1—H1A0.9600C12—C131.395 (4)
C1—H1B0.9600C13—C141.377 (5)
C1—H1C0.9600C13—H130.9300
C2—C31.540 (4)C14—C151.374 (6)
C3—C41.523 (4)C14—H140.9300
C4—H4A0.9600C15—C161.397 (4)
C4—H4B0.9600C15—H150.9300
C4—H4C0.9600C16—H160.9300
C5—C101.377 (4)
C6—N1—C3118.5 (2)C6—C5—O1121.2 (2)
C6—N1—H1120.8C5—C6—C7118.5 (3)
C3—N1—H1120.8C5—C6—N1119.3 (2)
C12—N2—C2118.6 (2)C7—C6—N1122.2 (3)
C12—N2—H2120.7C8—C7—C6120.7 (3)
C2—N2—H2120.7C8—C7—H7119.6
C5—O1—C2117.3 (2)C6—C7—H7119.6
C11—O2—C3116.8 (2)C9—C8—C7120.2 (3)
C2—C1—H1A109.5C9—C8—H8119.9
C2—C1—H1B109.5C7—C8—H8119.9
H1A—C1—H1B109.5C8—C9—C10120.1 (3)
C2—C1—H1C109.5C8—C9—H9119.9
H1A—C1—H1C109.5C10—C9—H9119.9
H1B—C1—H1C109.5C5—C10—C9118.8 (3)
N2—C2—O1107.15 (19)C5—C10—H10120.6
N2—C2—C1111.1 (2)C9—C10—H10120.6
O1—C2—C1107.8 (2)C16—C11—O2117.6 (3)
N2—C2—C3110.4 (2)C16—C11—C12121.4 (3)
O1—C2—C3107.34 (18)O2—C11—C12121.0 (2)
C1—C2—C3112.8 (2)N2—C12—C11119.6 (2)
N1—C3—O2106.42 (19)N2—C12—C13122.4 (3)
N1—C3—C4110.8 (2)C11—C12—C13118.0 (3)
O2—C3—C4107.9 (2)C14—C13—C12120.7 (3)
N1—C3—C2110.5 (2)C14—C13—H13119.6
O2—C3—C2107.48 (19)C12—C13—H13119.6
C4—C3—C2113.4 (2)C15—C14—C13120.7 (3)
C3—C4—H4A109.5C15—C14—H14119.6
C3—C4—H4B109.5C13—C14—H14119.6
H4A—C4—H4B109.5C14—C15—C16119.2 (3)
C3—C4—H4C109.5C14—C15—H15120.4
H4A—C4—H4C109.5C16—C15—H15120.4
H4B—C4—H4C109.5C11—C16—C15119.9 (3)
C10—C5—C6121.6 (3)C11—C16—H16120.0
C10—C5—O1117.1 (3)C15—C16—H16120.0
C12—N2—C2—O171.1 (3)O1—C5—C6—N14.7 (4)
C12—N2—C2—C1171.4 (2)C3—N1—C6—C519.2 (4)
C12—N2—C2—C345.5 (3)C3—N1—C6—C7162.8 (2)
C5—O1—C2—N2162.8 (2)C5—C6—C7—C80.7 (4)
C5—O1—C2—C177.5 (3)N1—C6—C7—C8178.7 (3)
C5—O1—C2—C344.3 (3)C6—C7—C8—C90.5 (5)
C6—N1—C3—O270.9 (3)C7—C8—C9—C100.2 (5)
C6—N1—C3—C4172.1 (2)C6—C5—C10—C90.5 (4)
C6—N1—C3—C245.5 (3)O1—C5—C10—C9176.7 (2)
C11—O2—C3—N1163.1 (2)C8—C9—C10—C50.7 (5)
C11—O2—C3—C477.9 (3)C3—O2—C11—C16162.5 (2)
C11—O2—C3—C244.7 (3)C3—O2—C11—C1219.7 (3)
N2—C2—C3—N1172.47 (18)C2—N2—C12—C1118.5 (4)
O1—C2—C3—N156.0 (3)C2—N2—C12—C13162.8 (2)
C1—C2—C3—N162.6 (3)C16—C11—C12—N2178.4 (3)
N2—C2—C3—O256.7 (2)O2—C11—C12—N23.9 (4)
O1—C2—C3—O259.7 (3)C16—C11—C12—C130.3 (4)
C1—C2—C3—O2178.3 (2)O2—C11—C12—C13177.4 (2)
N2—C2—C3—C462.4 (3)N2—C12—C13—C14179.2 (3)
O1—C2—C3—C4178.9 (2)C11—C12—C13—C140.5 (4)
C1—C2—C3—C462.5 (3)C12—C13—C14—C150.4 (5)
C2—O1—C5—C10162.8 (2)C13—C14—C15—C160.5 (6)
C2—O1—C5—C620.0 (3)O2—C11—C16—C15176.6 (2)
C10—C5—C6—C70.2 (4)C12—C11—C16—C151.1 (4)
O1—C5—C6—C7177.2 (2)C14—C15—C16—C111.3 (5)
C10—C5—C6—N1178.2 (3)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N1—H1···O2i0.862.553.122 (4)125
N2—H2···O1ii0.862.543.117 (3)126
Symmetry codes: (i) x, y+1/2, z+1/2; (ii) x, y+3/2, z+1/2.
 

Subscribe to Acta Crystallographica Section E: Crystallographic Communications

The full text of this article is available to subscribers to the journal.

If you have already registered and are using a computer listed in your registration details, please email support@iucr.org for assistance.

Buy online

You may purchase this article in PDF and/or HTML formats. For purchasers in the European Community who do not have a VAT number, VAT will be added at the local rate. Payments to the IUCr are handled by WorldPay, who will accept payment by credit card in several currencies. To purchase the article, please complete the form below (fields marked * are required), and then click on `Continue'.
E-mail address* 
Repeat e-mail address* 
(for error checking) 

Format*   PDF (US $40)
   HTML (US $40)
   PDF+HTML (US $50)
In order for VAT to be shown for your country javascript needs to be enabled.

VAT number 
(non-UK EC countries only) 
Country* 
 

Terms and conditions of use
Contact us

Follow Acta Cryst. E
Sign up for e-alerts
Follow Acta Cryst. on Twitter
Follow us on facebook
Sign up for RSS feeds