Buy article online - an online subscription or single-article purchase is required to access this article.
The carbazole unit of the title molecule, C
15H
9NO
3, is planar and forms dihedral angles of 3.08 (4)° with the attached carbaldehyde group and 0.75 (4)° with the fused oxazine ring. The dihedral angle between the two benzene rings is 2.09 (4)°. The structure is stabilized by inter- and intramolecular C—H
O hydrogen bonds.
Supporting information
CCDC reference: 647727
Key indicators
- Single-crystal X-ray study
- T = 203 K
- Mean (C-C) = 0.003 Å
- R factor = 0.045
- wR factor = 0.103
- Data-to-parameter ratio = 17.5
checkCIF/PLATON results
No syntax errors found
Alert level B
ABSTM02_ALERT_3_B The ratio of expected to reported Tmax/Tmin(RR') is < 0.75
Tmin and Tmax reported: 0.632 1.000
Tmin(prime) and Tmax expected: 0.931 0.975
RR(prime) = 0.662
Please check that your absorption correction is appropriate.
PLAT061_ALERT_3_B Tmax/Tmin Range Test RR' too Large ............. 0.66
PLAT230_ALERT_2_B Hirshfeld Test Diff for C4 - C41 .. 8.24 su
Alert level C
PLAT026_ALERT_3_C Ratio Observed / Unique Reflections too Low .... 42 Perc.
PLAT062_ALERT_4_C Rescale T(min) & T(max) by ..................... 0.98
PLAT063_ALERT_3_C Crystal Probably too Large for Beam Size ....... 0.65 mm
PLAT150_ALERT_1_C Volume as Calculated Differs from that Given ... 544.60 Ang-3
PLAT154_ALERT_1_C The su's on the Cell Angles are Equal (x 10000) 3000 Deg.
PLAT230_ALERT_2_C Hirshfeld Test Diff for O41 - C41 .. 5.77 su
PLAT230_ALERT_2_C Hirshfeld Test Diff for N11 - C1 .. 6.63 su
PLAT230_ALERT_2_C Hirshfeld Test Diff for C4 - C5 .. 6.08 su
0 ALERT level A = In general: serious problem
3 ALERT level B = Potentially serious problem
8 ALERT level C = Check and explain
0 ALERT level G = General alerts; check
2 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
4 ALERT type 2 Indicator that the structure model may be wrong or deficient
4 ALERT type 3 Indicator that the structure quality may be low
1 ALERT type 4 Improvement, methodology, query or suggestion
0 ALERT type 5 Informative message, check
Data collection: CrysAlis CCD (Oxford Diffraction, 2007); cell refinement: CrysAlis RED (Oxford Diffraction, 2007); data reduction: CrysAlis RED; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEP-3 (Farrugia, 1997); software used to prepare material for publication: PLATON (Spek, 2003).
1-Oxo-1,2-dihydro-1,4-oxazino[2,3,4-jk]carbazole-4-carbaldehyde
top
Crystal data top
C15H9NO3 | Z = 2 |
Mr = 251.23 | F(000) = 260 |
Triclinic, P1 | Dx = 1.532 Mg m−3 |
Hall symbol: -P 1 | Melting point = 436–438 K |
a = 6.811 (2) Å | Mo Kα radiation, λ = 0.71073 Å |
b = 8.751 (2) Å | Cell parameters from 10263 reflections |
c = 10.066 (4) Å | θ = 4.5–30.6° |
α = 111.84 (3)° | µ = 0.11 mm−1 |
β = 100.31 (3)° | T = 203 K |
γ = 91.98 (3)° | Small block, pale yellow |
V = 544.6 (3) Å3 | 0.65 × 0.45 × 0.23 mm |
Data collection top
Oxford Gemini diffractometer | 3013 independent reflections |
Radiation source: Enhance (Mo) X-ray Source | 1262 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.034 |
Detector resolution: 10.5081 pixels mm-1 | θmax = 30.7°, θmin = 4.7° |
φ and ω scans | h = −9→9 |
Absorption correction: multi-scan (SCALE3 ABSPACK in CrysAlis RED; Oxford Diffraction, 2007) | k = −12→11 |
Tmin = 0.632, Tmax = 1.000 | l = −13→14 |
7163 measured reflections | |
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)] = 0.045 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.103 | H-atom parameters constrained |
S = 0.82 | w = 1/[σ2(Fo2) + (0.0514P)2] where P = (Fo2 + 2Fc2)/3 |
3013 reflections | (Δ/σ)max = 0.012 |
172 parameters | Δρmax = 0.26 e Å−3 |
0 restraints | Δρmin = −0.25 e Å−3 |
Special details top
Geometry. Bond distances, angles etc. have been calculated using the rounded
fractional coordinates. All su'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 |
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 | |
O1 | 0.78186 (19) | 0.48821 (16) | 0.58296 (14) | 0.0545 (5) | |
O3 | 0.68494 (17) | 0.13315 (14) | 0.23366 (11) | 0.0427 (4) | |
O41 | 0.60345 (17) | −0.34645 (17) | −0.05178 (13) | 0.0530 (5) | |
N11 | 0.76183 (17) | 0.21236 (16) | 0.53957 (13) | 0.0280 (4) | |
C1 | 0.7559 (2) | 0.3435 (2) | 0.49782 (19) | 0.0372 (6) | |
C2 | 0.7156 (3) | 0.3010 (2) | 0.33438 (19) | 0.0497 (7) | |
C3a | 0.6972 (2) | 0.0115 (2) | 0.28673 (17) | 0.0265 (5) | |
C4 | 0.6703 (2) | −0.1558 (2) | 0.19577 (16) | 0.0271 (5) | |
C5 | 0.6849 (2) | −0.2748 (2) | 0.25926 (18) | 0.0333 (6) | |
C6 | 0.7244 (2) | −0.2321 (2) | 0.40937 (18) | 0.0337 (6) | |
C6a | 0.75053 (19) | −0.0642 (2) | 0.49986 (16) | 0.0266 (5) | |
C6b | 0.78905 (19) | 0.0336 (2) | 0.65749 (17) | 0.0272 (5) | |
C7 | 0.8166 (2) | −0.0088 (2) | 0.77943 (18) | 0.0339 (6) | |
C8 | 0.8473 (2) | 0.1174 (2) | 0.91659 (18) | 0.0365 (6) | |
C9 | 0.8495 (2) | 0.2817 (2) | 0.93357 (18) | 0.0379 (6) | |
C10 | 0.8231 (2) | 0.3280 (2) | 0.81498 (17) | 0.0341 (6) | |
C10a | 0.7946 (2) | 0.2012 (2) | 0.67862 (17) | 0.0289 (6) | |
C11a | 0.73489 (19) | 0.05022 (19) | 0.43522 (16) | 0.0252 (5) | |
C41 | 0.6236 (2) | −0.2062 (2) | 0.03521 (19) | 0.0377 (6) | |
H2A | 0.82856 | 0.35534 | 0.31435 | 0.0597* | |
H2B | 0.59648 | 0.35314 | 0.31055 | 0.0597* | |
H5 | 0.66717 | −0.38758 | 0.19748 | 0.0400* | |
H6 | 0.73325 | −0.31394 | 0.44908 | 0.0405* | |
H7 | 0.81444 | −0.12027 | 0.76885 | 0.0406* | |
H8 | 0.86709 | 0.09080 | 0.99998 | 0.0438* | |
H9 | 0.86952 | 0.36409 | 1.02833 | 0.0455* | |
H10 | 0.82439 | 0.43962 | 0.82646 | 0.0409* | |
H41 | 0.60843 | −0.12203 | −0.00149 | 0.0453* | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
O1 | 0.0894 (10) | 0.0299 (8) | 0.0356 (8) | 0.0024 (7) | 0.0067 (7) | 0.0061 (7) |
O3 | 0.0703 (8) | 0.0295 (8) | 0.0256 (7) | 0.0032 (6) | 0.0065 (6) | 0.0092 (6) |
O41 | 0.0637 (8) | 0.0449 (9) | 0.0371 (8) | 0.0083 (6) | 0.0085 (6) | 0.0014 (7) |
N11 | 0.0349 (7) | 0.0252 (8) | 0.0206 (8) | 0.0026 (6) | 0.0029 (5) | 0.0066 (7) |
C1 | 0.0450 (10) | 0.0329 (12) | 0.0298 (11) | 0.0033 (8) | 0.0042 (8) | 0.0094 (9) |
C2 | 0.0804 (13) | 0.0314 (12) | 0.0313 (11) | −0.0029 (9) | 0.0022 (9) | 0.0102 (9) |
C3a | 0.0255 (8) | 0.0276 (10) | 0.0280 (10) | 0.0021 (7) | 0.0057 (7) | 0.0125 (8) |
C4 | 0.0238 (8) | 0.0289 (10) | 0.0241 (9) | 0.0017 (7) | 0.0035 (6) | 0.0058 (8) |
C5 | 0.0303 (9) | 0.0285 (11) | 0.0334 (11) | 0.0031 (7) | 0.0053 (7) | 0.0038 (8) |
C6 | 0.0340 (9) | 0.0325 (11) | 0.0347 (11) | 0.0050 (7) | 0.0059 (8) | 0.0134 (9) |
C6a | 0.0205 (8) | 0.0286 (10) | 0.0278 (10) | 0.0018 (7) | 0.0040 (7) | 0.0081 (8) |
C6b | 0.0222 (8) | 0.0331 (10) | 0.0243 (10) | 0.0038 (7) | 0.0042 (7) | 0.0089 (8) |
C7 | 0.0301 (9) | 0.0369 (11) | 0.0340 (11) | 0.0040 (7) | 0.0039 (7) | 0.0141 (9) |
C8 | 0.0301 (9) | 0.0535 (14) | 0.0254 (10) | 0.0034 (8) | 0.0033 (7) | 0.0157 (10) |
C9 | 0.0325 (9) | 0.0488 (13) | 0.0225 (10) | 0.0011 (8) | 0.0024 (7) | 0.0043 (9) |
C10 | 0.0359 (9) | 0.0325 (11) | 0.0276 (10) | 0.0006 (7) | 0.0041 (7) | 0.0059 (9) |
C10a | 0.0220 (8) | 0.0384 (11) | 0.0249 (10) | 0.0045 (7) | 0.0041 (7) | 0.0107 (8) |
C11a | 0.0227 (8) | 0.0246 (10) | 0.0226 (9) | 0.0013 (7) | 0.0041 (6) | 0.0032 (8) |
C41 | 0.0334 (10) | 0.0339 (12) | 0.0332 (11) | 0.0011 (8) | 0.0049 (8) | −0.0003 (9) |
Geometric parameters (Å, º) top
O1—C1 | 1.222 (2) | C6b—C7 | 1.393 (2) |
O3—C2 | 1.423 (2) | C6b—C10a | 1.400 (3) |
O3—C3a | 1.356 (2) | C7—C8 | 1.384 (2) |
O41—C41 | 1.199 (2) | C8—C9 | 1.383 (3) |
N11—C1 | 1.361 (2) | C9—C10 | 1.382 (2) |
N11—C10a | 1.418 (2) | C10—C10a | 1.382 (2) |
N11—C11a | 1.398 (2) | C2—H2A | 0.9800 |
C1—C2 | 1.515 (3) | C2—H2B | 0.9800 |
C3a—C4 | 1.393 (3) | C5—H5 | 0.9400 |
C3a—C11a | 1.377 (2) | C6—H6 | 0.9400 |
C4—C5 | 1.408 (3) | C7—H7 | 0.9400 |
C4—C41 | 1.478 (2) | C8—H8 | 0.9400 |
C5—C6 | 1.387 (2) | C9—H9 | 0.9400 |
C6—C6a | 1.396 (3) | C10—H10 | 0.9400 |
C6a—C6b | 1.464 (2) | C41—H41 | 0.9400 |
C6a—C11a | 1.380 (3) | | |
| | | |
O1···C10 | 3.119 (3) | C8···C4vii | 3.572 (2) |
O3···N11 | 2.8366 (19) | C8···C41vii | 3.402 (2) |
O3···C41i | 3.390 (2) | C9···C41vii | 3.360 (2) |
O41···C10ii | 3.213 (3) | C9···C4vii | 3.529 (2) |
O41···C2i | 3.415 (3) | C10···O1 | 3.119 (3) |
O1···H2Aiii | 2.7700 | C10···C5viii | 3.571 (2) |
O1···H10 | 2.6100 | C10···C5vii | 3.384 (2) |
O1···H6iv | 2.5600 | C10···O41ix | 3.213 (3) |
O3···H41i | 2.7600 | C10a···C6viii | 3.570 (2) |
O3···H41 | 2.5300 | C10a···C5viii | 3.482 (2) |
O3···H8v | 2.7600 | C10a···C6vii | 3.532 (2) |
O41···H5 | 2.6300 | C10a···C5vii | 3.471 (2) |
O41···H10ii | 2.5300 | C11a···C6bviii | 3.558 (2) |
O41···H2Bi | 2.6900 | C11a···C6avii | 3.481 (2) |
O41···H5vi | 2.6800 | C11a···C6bvii | 3.502 (2) |
N11···O3 | 2.8366 (19) | C11a···C6aviii | 3.438 (2) |
N11···C6vii | 3.442 (2) | C41···C8viii | 3.567 (2) |
N11···C6viii | 3.433 (2) | C41···C8vii | 3.402 (2) |
C2···O41i | 3.415 (3) | C41···O3i | 3.390 (2) |
C3a···C6bviii | 3.503 (2) | C41···C9vii | 3.360 (2) |
C3a···C6bvii | 3.490 (2) | C1···H10 | 3.0400 |
C3a···C7vii | 3.441 (2) | C8···H8x | 2.9300 |
C3a···C7viii | 3.492 (2) | C8···H41xi | 3.0400 |
C4···C9vii | 3.529 (2) | C10···H9xii | 3.0700 |
C4···C8vii | 3.572 (2) | H2A···O1iii | 2.7700 |
C5···C10avii | 3.471 (2) | H2B···O41i | 2.6900 |
C5···C10vii | 3.384 (2) | H5···O41 | 2.6300 |
C5···C10viii | 3.571 (2) | H5···O41vi | 2.6800 |
C5···C10aviii | 3.482 (2) | H6···O1xiii | 2.5600 |
C6···C10aviii | 3.570 (2) | H8···O3xi | 2.7600 |
C6···N11vii | 3.442 (2) | H8···H41xi | 2.5100 |
C6···N11viii | 3.433 (2) | H8···C8x | 2.9300 |
C6···C10avii | 3.532 (2) | H8···H8x | 2.4500 |
C6a···C11aviii | 3.438 (2) | H9···C10xii | 3.0700 |
C6a···C6aviii | 3.541 (2) | H9···H10xii | 2.5000 |
C6a···C11avii | 3.481 (2) | H10···O1 | 2.6100 |
C6b···C11aviii | 3.558 (2) | H10···O41ix | 2.5300 |
C6b···C3avii | 3.490 (2) | H10···C1 | 3.0400 |
C6b···C3aviii | 3.503 (2) | H10···H9xii | 2.5000 |
C6b···C11avii | 3.502 (2) | H41···O3 | 2.5300 |
C7···C3avii | 3.441 (2) | H41···C8v | 3.0400 |
C7···C3aviii | 3.492 (2) | H41···H8v | 2.5100 |
C8···C41viii | 3.567 (2) | H41···O3i | 2.7600 |
| | | |
C2—O3—C3a | 118.71 (13) | N11—C10a—C6b | 108.28 (14) |
C1—N11—C10a | 132.54 (15) | N11—C10a—C10 | 128.40 (17) |
C1—N11—C11a | 120.63 (14) | C6b—C10a—C10 | 123.31 (16) |
C10a—N11—C11a | 106.83 (14) | N11—C11a—C3a | 123.58 (16) |
O1—C1—N11 | 124.12 (16) | N11—C11a—C6a | 111.60 (13) |
O1—C1—C2 | 120.07 (17) | C3a—C11a—C6a | 124.82 (16) |
N11—C1—C2 | 115.81 (15) | O41—C41—C4 | 124.89 (18) |
O3—C2—C1 | 120.82 (16) | O3—C2—H2A | 107.00 |
O3—C3a—C4 | 122.37 (14) | O3—C2—H2B | 107.00 |
O3—C3a—C11a | 120.43 (16) | C1—C2—H2A | 107.00 |
C4—C3a—C11a | 117.19 (17) | C1—C2—H2B | 107.00 |
C3a—C4—C5 | 118.99 (15) | H2A—C2—H2B | 107.00 |
C3a—C4—C41 | 120.01 (16) | C4—C5—H5 | 119.00 |
C5—C4—C41 | 120.99 (16) | C6—C5—H5 | 119.00 |
C4—C5—C6 | 122.56 (17) | C5—C6—H6 | 121.00 |
C5—C6—C6a | 118.14 (17) | C6a—C6—H6 | 121.00 |
C6—C6a—C6b | 136.41 (17) | C6b—C7—H7 | 121.00 |
C6—C6a—C11a | 118.30 (14) | C8—C7—H7 | 121.00 |
C6b—C6a—C11a | 105.28 (15) | C7—C8—H8 | 119.00 |
C6a—C6b—C7 | 133.12 (17) | C9—C8—H8 | 119.00 |
C6a—C6b—C10a | 108.02 (15) | C8—C9—H9 | 119.00 |
C7—C6b—C10a | 118.85 (15) | C10—C9—H9 | 119.00 |
C6b—C7—C8 | 118.28 (17) | C9—C10—H10 | 122.00 |
C7—C8—C9 | 121.41 (16) | C10a—C10—H10 | 122.00 |
C8—C9—C10 | 121.77 (16) | O41—C41—H41 | 118.00 |
C9—C10—C10a | 116.37 (17) | C4—C41—H41 | 118.00 |
| | | |
C3a—O3—C2—C1 | −1.6 (2) | C41—C4—C5—C6 | −178.65 (14) |
C2—O3—C3a—C4 | −179.64 (15) | C3a—C4—C41—O41 | 177.81 (15) |
C2—O3—C3a—C11a | 1.2 (2) | C5—C4—C41—O41 | −3.3 (2) |
C10a—N11—C1—O1 | 0.5 (3) | C4—C5—C6—C6a | 0.0 (2) |
C10a—N11—C1—C2 | −179.97 (15) | C5—C6—C6a—C6b | 178.52 (15) |
C11a—N11—C1—O1 | −178.58 (14) | C5—C6—C6a—C11a | 0.3 (2) |
C11a—N11—C1—C2 | 1.0 (2) | C6—C6a—C6b—C7 | 0.8 (3) |
C1—N11—C10a—C6b | −178.65 (14) | C6—C6a—C6b—C10a | −178.49 (16) |
C1—N11—C10a—C10 | 2.8 (3) | C11a—C6a—C6b—C7 | 179.18 (15) |
C11a—N11—C10a—C6b | 0.52 (15) | C11a—C6a—C6b—C10a | −0.07 (15) |
C11a—N11—C10a—C10 | −178.01 (14) | C6—C6a—C11a—N11 | 179.16 (12) |
C1—N11—C11a—C3a | −1.4 (2) | C6—C6a—C11a—C3a | −0.7 (2) |
C1—N11—C11a—C6a | 178.70 (13) | C6b—C6a—C11a—N11 | 0.40 (15) |
C10a—N11—C11a—C3a | 179.32 (13) | C6b—C6a—C11a—C3a | −179.50 (13) |
C10a—N11—C11a—C6a | −0.58 (16) | C6a—C6b—C7—C8 | −178.85 (14) |
O1—C1—C2—O3 | −179.97 (16) | C10a—C6b—C7—C8 | 0.3 (2) |
N11—C1—C2—O3 | 0.5 (2) | C6a—C6b—C10a—N11 | −0.28 (15) |
O3—C3a—C4—C5 | −179.85 (13) | C6a—C6b—C10a—C10 | 178.34 (13) |
O3—C3a—C4—C41 | −0.9 (2) | C7—C6b—C10a—N11 | −179.66 (12) |
C11a—C3a—C4—C5 | −0.7 (2) | C7—C6b—C10a—C10 | −1.0 (2) |
C11a—C3a—C4—C41 | 178.26 (13) | C6b—C7—C8—C9 | 0.5 (2) |
O3—C3a—C11a—N11 | 0.3 (2) | C7—C8—C9—C10 | −0.6 (2) |
O3—C3a—C11a—C6a | −179.86 (13) | C8—C9—C10—C10a | −0.1 (2) |
C4—C3a—C11a—N11 | −178.95 (13) | C9—C10—C10a—N11 | 179.21 (14) |
C4—C3a—C11a—C6a | 0.9 (2) | C9—C10—C10a—C6b | 0.9 (2) |
C3a—C4—C5—C6 | 0.3 (2) | | |
Symmetry codes: (i) −x+1, −y, −z; (ii) x, y−1, z−1; (iii) −x+2, −y+1, −z+1; (iv) x, y+1, z; (v) x, y, z−1; (vi) −x+1, −y−1, −z; (vii) −x+1, −y, −z+1; (viii) −x+2, −y, −z+1; (ix) x, y+1, z+1; (x) −x+2, −y, −z+2; (xi) x, y, z+1; (xii) −x+2, −y+1, −z+2; (xiii) x, y−1, z. |
Hydrogen-bond geometry (Å, º) top
D—H···A | D—H | H···A | D···A | D—H···A |
C6—H6···O1xiii | 0.94 | 2.56 | 3.493 (3) | 174 |
C10—H10···O41ix | 0.94 | 2.53 | 3.213 (3) | 129 |
C41—H41···O3 | 0.94 | 2.53 | 2.861 (2) | 101 |
Symmetry codes: (ix) x, y+1, z+1; (xiii) x, y−1, z. |
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.