1-Oxo-1,2-dihydro-1,4-oxazino[2,3,4-jk]carbazole-4-carbaldehyde

Gunaseelan, A.T.; Thiruvalluvar, A.; Martin, A.E.; Prasad, K.J.R.; Butcher, R.J.

doi:10.1107/S1600536807016133

1-Oxo-1,2-dihydro-1,4-oxazino[2,3,4-jk]carbazole-4-carbaldehyde

A. T. Gunaseelan, A. Thiruvalluvar, A. E. Martin, K. J. R. Prasad and R. J. Butcher

The carbazole unit of the title molecule, C₁₅H₉NO₃, 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.

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Supporting information

	Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536807016133/at2252sup1.cif Contains datablocks global, I
	Structure factor file (CIF format) https://doi.org/10.1107/S1600536807016133/at2252Isup2.hkl Contains datablock I

CCDC reference: 647727

checkCIF report

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

Computing details top

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
M_r = 251.23	F(000) = 260
Triclinic, P1	D_x = 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	R_int = 0.034
Detector resolution: 10.5081 pixels mm^-1	θ_max = 30.7°, θ_min = 4.7°
φ and ω scans	h = −9→9
Absorption correction: multi-scan (SCALE3 ABSPACK in CrysAlis RED; Oxford Diffraction, 2007)	k = −12→11
T_min = 0.632, T_max = 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(F_o²) + (0.0514P)²] where P = (F_o² + 2F_c²)/3
3013 reflections	(Δ/σ)_max = 0.012
172 parameters	Δρ_max = 0.26 e Å⁻³
0 restraints	Δρ_min = −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	U_iso*/U_eq
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···C4^vii	3.572 (2)
O3···N11	2.8366 (19)	C8···C41^vii	3.402 (2)
O3···C41ⁱ	3.390 (2)	C9···C41^vii	3.360 (2)
O41···C10ⁱⁱ	3.213 (3)	C9···C4^vii	3.529 (2)
O41···C2ⁱ	3.415 (3)	C10···O1	3.119 (3)
O1···H2Aⁱⁱⁱ	2.7700	C10···C5^viii	3.571 (2)
O1···H10	2.6100	C10···C5^vii	3.384 (2)
O1···H6^iv	2.5600	C10···O41^ix	3.213 (3)
O3···H41ⁱ	2.7600	C10a···C6^viii	3.570 (2)
O3···H41	2.5300	C10a···C5^viii	3.482 (2)
O3···H8^v	2.7600	C10a···C6^vii	3.532 (2)
O41···H5	2.6300	C10a···C5^vii	3.471 (2)
O41···H10ⁱⁱ	2.5300	C11a···C6b^viii	3.558 (2)
O41···H2Bⁱ	2.6900	C11a···C6a^vii	3.481 (2)
O41···H5^vi	2.6800	C11a···C6b^vii	3.502 (2)
N11···O3	2.8366 (19)	C11a···C6a^viii	3.438 (2)
N11···C6^vii	3.442 (2)	C41···C8^viii	3.567 (2)
N11···C6^viii	3.433 (2)	C41···C8^vii	3.402 (2)
C2···O41ⁱ	3.415 (3)	C41···O3ⁱ	3.390 (2)
C3a···C6b^viii	3.503 (2)	C41···C9^vii	3.360 (2)
C3a···C6b^vii	3.490 (2)	C1···H10	3.0400
C3a···C7^vii	3.441 (2)	C8···H8^x	2.9300
C3a···C7^viii	3.492 (2)	C8···H41^xi	3.0400
C4···C9^vii	3.529 (2)	C10···H9^xii	3.0700
C4···C8^vii	3.572 (2)	H2A···O1ⁱⁱⁱ	2.7700
C5···C10a^vii	3.471 (2)	H2B···O41ⁱ	2.6900
C5···C10^vii	3.384 (2)	H5···O41	2.6300
C5···C10^viii	3.571 (2)	H5···O41^vi	2.6800
C5···C10a^viii	3.482 (2)	H6···O1^xiii	2.5600
C6···C10a^viii	3.570 (2)	H8···O3^xi	2.7600
C6···N11^vii	3.442 (2)	H8···H41^xi	2.5100
C6···N11^viii	3.433 (2)	H8···C8^x	2.9300
C6···C10a^vii	3.532 (2)	H8···H8^x	2.4500
C6a···C11a^viii	3.438 (2)	H9···C10^xii	3.0700
C6a···C6a^viii	3.541 (2)	H9···H10^xii	2.5000
C6a···C11a^vii	3.481 (2)	H10···O1	2.6100
C6b···C11a^viii	3.558 (2)	H10···O41^ix	2.5300
C6b···C3a^vii	3.490 (2)	H10···C1	3.0400
C6b···C3a^viii	3.503 (2)	H10···H9^xii	2.5000
C6b···C11a^vii	3.502 (2)	H41···O3	2.5300
C7···C3a^vii	3.441 (2)	H41···C8^v	3.0400
C7···C3a^viii	3.492 (2)	H41···H8^v	2.5100
C8···C41^viii	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···O1^xiii	0.94	2.56	3.493 (3)	174
C10—H10···O41^ix	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.

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