Methyl 1-oxo-2,3,4,9-tetra­hydro-1H-carbazole-2-carboxyl­ate

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

doi:10.1107/S1600536807035660

Methyl 1-oxo-2,3,4,9-tetrahydro-1H-carbazole-2-carboxylate

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

In the title molecule, C₁₄H₁₃NO₃, the dihedral angle between the benzene ring and the fused pyrrole ring is 1.0 (1)°. The cyclohexene ring adopts a twist conformation. Three C atoms of the cyclohexene ring, with their attached H atoms, and all atoms of the ester group, are disordered over two positions; the site-occupancy factors are ca 0.88 and 0.12. The crystal structure is stabilized by intermolecular N—H

O and C—H

O hydrogen bonds.

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Supporting information

	Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536807035660/wn2176sup1.cif Contains datablocks global, I
	Structure factor file (CIF format) https://doi.org/10.1107/S1600536807035660/wn2176Isup2.hkl Contains datablock I

CCDC reference: 657857

checkCIF report

Key indicators

Single-crystal X-ray study
T = 203 K
Mean (C-C) = 0.003 Å
Disorder in main residue
R factor = 0.067
wR factor = 0.221
Data-to-parameter ratio = 18.0

checkCIF/PLATON results

No syntax errors found



Alert level B
DIFMX01_ALERT_2_B  The maximum difference density is > 0.1*ZMAX*1.00
            _refine_diff_density_max given =      0.804
            Test value =      0.800

Alert level C
DIFMX02_ALERT_1_C  The maximum difference density is > 0.1*ZMAX*0.75
            The relevant atom site should be identified.
PLAT062_ALERT_4_C Rescale T(min) & T(max) by .....................       0.98
PLAT097_ALERT_2_C Maximum (Positive) Residual Density ............       0.80 e/A   
PLAT301_ALERT_3_C Main Residue  Disorder .........................      25.00 Perc.
PLAT366_ALERT_2_C Short? C(sp?)-C(sp?) Bond  C9A    -   C41    ...       1.38 Ang.

Alert level G
PLAT793_ALERT_1_G Check the Absolute Configuration of C2A    = ...          R
PLAT860_ALERT_3_G Note: Number of Least-Squares Restraints .......          6

   0 ALERT level A = In general: serious problem
   1 ALERT level B = Potentially serious problem
   5 ALERT level C = Check and explain
   2 ALERT level G = General alerts; check

   2 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
   0 ALERT type 5 Informative message, check

Comment top

The title compound, has been analysed as part of our crystallographic studies on substituted carbazoles (Gunaseelan et al. (2007a, b); Thiruvalluvar et al. (2007)).

The molecular structure of the title compound, with the atomic numbering scheme, is shown in Fig. 1. The dihedral angle between the benzene ring and the fused pyrrole ring is 1.0 (1)°. The cyclohexene ring adopts a twist conformation. The crystal structure is stabilized by intermolecular N9—H9···O1(-x + 1,-y + 1,-z) and C14A—H14B···O2A(-x + 1,-y + 1,-z + 1) hydrogen bonds (Fig. 2).

Related literature top

For related literature, see: Gunaseelan et al. (2007a,b); Thiruvalluvar et al. (2007).

Experimental top

A mixture of methyl 2-(1-oxo-2,3,4,9-tetrahydro-1H-carbazol-2-yl) oxoacetate (270 mg, 0.001 mol), glass powder (500 mg) and iron powder (500 mg) in diphenyl ether (15 ml) was heated at 443–473 K for 30 min. Carbon monoxide was liberated during heating. After cooling, the mixture was extracted with ethyl acetate and purified by column chromatography over silica gel using petroleum ether/ethyl acetate (95:5 v/v) as eluant to obtain the pure title compound (100 mg, 40%), which was recrystallized from glacial acetic acid.

Structure description top

The title compound, has been analysed as part of our crystallographic studies on substituted carbazoles (Gunaseelan et al. (2007a, b); Thiruvalluvar et al. (2007)).

For related literature, see: Gunaseelan et al. (2007a,b); Thiruvalluvar et al. (2007).

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).

Figures top

	Fig. 1. The molecular structure of the title compound, showing the atom-numbering scheme and displacement ellipsoids drawn at the 50% probability level. H atoms involved in hydrogen bonding have been labelled. Only the major disorder component is shown.
	Fig. 2. The molecular packing of the title compound, viewed down the a axis. Dashed lines indicate hydrogen bonds. H atoms not involved in hydrogen bonding have been omitted. Only the major disorder component is shown.

Methyl 1-oxo-2,3,4,9-tetrahydro-1H-carbazole-2-carboxylate top

Crystal data top

C₁₄H₁₃NO₃	Z = 2
M_r = 243.25	F(000) = 256
Triclinic, P1	D_x = 1.380 Mg m⁻³
Hall symbol: -P 1	Melting point: 409(1) K
a = 6.9814 (12) Å	Mo Kα radiation, λ = 0.71073 Å
b = 8.1303 (13) Å	Cell parameters from 2541 reflections
c = 10.780 (2) Å	θ = 4.8–30.6°
α = 88.575 (14)°	µ = 0.10 mm⁻¹
β = 76.881 (15)°	T = 203 K
γ = 79.367 (14)°	Plate, light-brown
V = 585.59 (18) Å³	0.36 × 0.31 × 0.22 mm

Data collection top

Oxford Diffraction Gemini diffractometer	3176 independent reflections
Radiation source: fine-focus sealed tube	1673 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.023
Detector resolution: 10.5081 pixels mm^-1	θ_max = 30.7°, θ_min = 4.8°
φ and ω scans	h = −9→9
Absorption correction: multi-scan (CrysAlis RED; Oxford Diffraction, 2007)	k = −11→11
T_min = 0.890, T_max = 1.000	l = −12→14
6572 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)] = 0.067	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.221	H-atom parameters constrained
S = 1.11	w = 1/[σ²(F_o²) + (0.1197P)²] where P = (F_o² + 2F_c²)/3
3176 reflections	(Δ/σ)_max < 0.001
176 parameters	Δρ_max = 0.80 e Å⁻³
6 restraints	Δρ_min = −0.44 e Å⁻³

Crystal data top

C₁₄H₁₃NO₃	γ = 79.367 (14)°
M_r = 243.25	V = 585.59 (18) Å³
Triclinic, P1	Z = 2
a = 6.9814 (12) Å	Mo Kα radiation
b = 8.1303 (13) Å	µ = 0.10 mm⁻¹
c = 10.780 (2) Å	T = 203 K
α = 88.575 (14)°	0.36 × 0.31 × 0.22 mm
β = 76.881 (15)°

Data collection top

Oxford Diffraction Gemini diffractometer	3176 independent reflections
Absorption correction: multi-scan (CrysAlis RED; Oxford Diffraction, 2007)	1673 reflections with I > 2σ(I)
T_min = 0.890, T_max = 1.000	R_int = 0.023
6572 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.067	6 restraints
wR(F²) = 0.221	H-atom parameters constrained
S = 1.11	Δρ_max = 0.80 e Å⁻³
3176 reflections	Δρ_min = −0.44 e Å⁻³
176 parameters

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	Occ. (<1)
C1	0.2838 (3)	0.6953 (3)	0.1859 (2)	0.0373 (5)
O1	0.4523 (2)	0.6125 (2)	0.17505 (15)	0.0468 (5)
C5	−0.2646 (3)	0.8206 (3)	−0.0495 (2)	0.0478 (6)
H5	−0.3758	0.8873	0.0038	0.057*
C6	−0.2759 (4)	0.7722 (3)	−0.1673 (3)	0.0521 (7)
H6	−0.3949	0.8067	−0.1952	0.063*
C7	−0.1117 (4)	0.6713 (3)	−0.2474 (2)	0.0493 (6)
H7	−0.1228	0.6397	−0.3284	0.059*
C8	0.0649 (3)	0.6177 (3)	−0.2100 (2)	0.0412 (6)
H8	0.1742	0.5498	−0.2640	0.049*
C8A	0.0767 (3)	0.6671 (3)	−0.0902 (2)	0.0348 (5)
N9	0.2302 (2)	0.6317 (2)	−0.02795 (16)	0.0356 (5)
H9	0.3471	0.5707	−0.0583	0.043*
C9A	0.1692 (3)	0.7085 (3)	0.0902 (2)	0.0357 (5)
C41	−0.0244 (3)	0.7963 (3)	0.1053 (2)	0.0376 (5)
C42	−0.0870 (3)	0.7707 (3)	−0.0082 (2)	0.0362 (5)
C13	0.2754 (3)	0.7454 (3)	0.4124 (2)	0.0490 (7)
C2A	0.1862 (4)	0.8086 (4)	0.3039 (3)	0.0398 (7)	0.879 (3)
H2A	0.2226	0.9198	0.2832	0.048*	0.879 (3)
C3A	−0.0392 (4)	0.8347 (4)	0.3339 (3)	0.0579 (8)	0.879 (3)
H31A	−0.0801	0.7290	0.3642	0.069*	0.879 (3)
H31B	−0.0918	0.9171	0.4037	0.069*	0.879 (3)
C4A	−0.1345 (4)	0.8929 (3)	0.2245 (2)	0.0503 (7)	0.879 (3)
H4A	−0.2742	0.8778	0.2451	0.060*	0.879 (3)
H4B	−0.1330	1.0124	0.2112	0.060*	0.879 (3)
O2A	0.2322 (3)	0.6162 (2)	0.47104 (18)	0.0558 (6)	0.879 (3)
O3A	0.3986 (3)	0.8286 (3)	0.4441 (2)	0.0502 (6)	0.879 (3)
C14A	0.4832 (4)	0.7645 (4)	0.5509 (3)	0.0583 (7)	0.879 (3)
H14A	0.5682	0.8382	0.5692	0.087*	0.879 (3)
H14B	0.5618	0.6533	0.5297	0.087*	0.879 (3)
H14C	0.3760	0.7591	0.6252	0.087*	0.879 (3)
C2B	0.146 (3)	0.742 (3)	0.325 (2)	0.0398 (7)	0.121 (3)
H2B	0.1077	0.6313	0.3477	0.048*	0.121 (3)
C3B	−0.0392 (4)	0.8347 (4)	0.3339 (3)	0.0579 (8)	0.121 (3)
H32A	−0.0423	0.9362	0.3819	0.069*	0.121 (3)
H32B	−0.1319	0.7723	0.3890	0.069*	0.121 (3)
C4B	−0.1345 (4)	0.8929 (3)	0.2245 (2)	0.0503 (7)	0.121 (3)
H41	−0.2742	0.8778	0.2451	0.060*	0.121 (3)
H42	−0.1330	1.0124	0.2112	0.060*	0.121 (3)
O2B	0.347 (2)	0.8761 (13)	0.3797 (16)	0.0558 (6)	0.121 (3)
O3B	0.3399 (16)	0.6820 (11)	0.5095 (8)	0.0502 (6)	0.121 (3)
C14B	0.4832 (4)	0.7645 (4)	0.5509 (3)	0.0583 (7)	0.121 (3)
H14D	0.4959	0.7267	0.6353	0.087*	0.121 (3)
H14E	0.4370	0.8847	0.5535	0.087*	0.121 (3)
H14F	0.6123	0.7370	0.4917	0.087*	0.121 (3)

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
C1	0.0329 (11)	0.0413 (12)	0.0319 (12)	−0.0019 (9)	0.0017 (9)	−0.0063 (9)
O1	0.0336 (8)	0.0562 (10)	0.0431 (10)	0.0059 (7)	−0.0037 (7)	−0.0127 (8)
C5	0.0379 (12)	0.0466 (14)	0.0535 (16)	0.0005 (10)	−0.0071 (11)	0.0114 (11)
C6	0.0425 (13)	0.0549 (15)	0.0598 (17)	−0.0063 (12)	−0.0172 (12)	0.0173 (13)
C7	0.0574 (15)	0.0525 (14)	0.0437 (14)	−0.0184 (12)	−0.0173 (11)	0.0063 (11)
C8	0.0435 (12)	0.0370 (12)	0.0412 (13)	−0.0080 (10)	−0.0058 (10)	0.0030 (10)
C8A	0.0357 (11)	0.0313 (11)	0.0358 (12)	−0.0073 (8)	−0.0041 (9)	0.0040 (9)
N9	0.0281 (9)	0.0399 (10)	0.0341 (10)	−0.0007 (7)	−0.0009 (7)	−0.0058 (8)
C9A	0.0332 (11)	0.0326 (11)	0.0366 (12)	−0.0026 (9)	−0.0009 (9)	−0.0033 (9)
C41	0.0324 (11)	0.0320 (11)	0.0404 (12)	0.0035 (8)	0.0009 (9)	−0.0019 (9)
C42	0.0328 (11)	0.0319 (11)	0.0392 (12)	−0.0011 (8)	−0.0030 (9)	0.0060 (9)
C13	0.0426 (13)	0.0516 (15)	0.0446 (14)	−0.0052 (11)	0.0066 (10)	−0.0231 (12)
C2A	0.0448 (15)	0.0333 (15)	0.0356 (14)	−0.0027 (12)	−0.0004 (11)	−0.0086 (12)
C3A	0.0425 (13)	0.0701 (18)	0.0487 (15)	0.0139 (12)	−0.0021 (11)	−0.0228 (13)
C4A	0.0436 (13)	0.0478 (14)	0.0471 (15)	0.0086 (11)	0.0021 (11)	−0.0067 (11)
O2A	0.0706 (14)	0.0513 (12)	0.0476 (12)	−0.0167 (10)	−0.0134 (10)	0.0046 (10)
O3A	0.0525 (12)	0.0491 (11)	0.0515 (13)	−0.0132 (9)	−0.0128 (9)	−0.0048 (10)
C14A	0.0597 (16)	0.0636 (17)	0.0539 (16)	−0.0092 (13)	−0.0189 (13)	−0.0027 (13)
C2B	0.0448 (15)	0.0333 (15)	0.0356 (14)	−0.0027 (12)	−0.0004 (11)	−0.0086 (12)
C3B	0.0425 (13)	0.0701 (18)	0.0487 (15)	0.0139 (12)	−0.0021 (11)	−0.0228 (13)
C4B	0.0436 (13)	0.0478 (14)	0.0471 (15)	0.0086 (11)	0.0021 (11)	−0.0067 (11)
O2B	0.0706 (14)	0.0513 (12)	0.0476 (12)	−0.0167 (10)	−0.0134 (10)	0.0046 (10)
O3B	0.0525 (12)	0.0491 (11)	0.0515 (13)	−0.0132 (9)	−0.0128 (9)	−0.0048 (10)
C14B	0.0597 (16)	0.0636 (17)	0.0539 (16)	−0.0092 (13)	−0.0189 (13)	−0.0027 (13)

Geometric parameters (Å, º) top

O1—C1	1.225 (3)	C8—C8A	1.386 (3)
O2A—C13	1.262 (3)	C8A—C42	1.422 (3)
O2B—C13	1.265 (12)	C9A—C41	1.383 (3)
O3A—C13	1.293 (3)	C41—C42	1.422 (3)
O3A—C14A	1.454 (4)	C2A—H2A	0.9900
O3B—C13	1.290 (10)	C2B—H2B	0.9900
O3B—C14B	1.455 (11)	C3A—H31A	0.9800
N9—C8A	1.373 (3)	C3A—H31B	0.9800
N9—C9A	1.374 (3)	C3B—H32A	0.9800
N9—H9	0.8700	C3B—H32B	0.9800
C1—C2B	1.60 (2)	C4A—H4A	0.9800
C1—C2A	1.538 (4)	C4A—H4B	0.9800
C1—C9A	1.433 (3)	C4B—H41	0.9800
C2A—C13	1.485 (4)	C4B—H42	0.9800
C2A—C3A	1.508 (4)	C5—H5	0.9400
C2B—C3B	1.36 (2)	C6—H6	0.9400
C2B—C13	1.45 (2)	C7—H7	0.9400
C3A—C4A	1.506 (4)	C8—H8	0.9400
C3B—C4B	1.506 (4)	C14A—H14B	0.9700
C4A—C41	1.497 (3)	C14A—H14C	0.9700
C4B—C41	1.497 (3)	C14A—H14A	0.9700
C5—C42	1.398 (3)	C14B—H14D	0.9700
C5—C6	1.362 (4)	C14B—H14E	0.9700
C6—C7	1.404 (4)	C14B—H14F	0.9700
C7—C8	1.376 (4)

O1···O2A	3.210 (3)	C9A···H31A	3.0600
O1···N9	2.941 (2)	C14A···H6^xiii	3.0900
O1···C5ⁱ	3.389 (3)	C14B···H6^xiii	3.0900
O1···O2B	2.986 (14)	C14B···H32Bⁱ	2.8600
O1···N9ⁱⁱ	2.883 (2)	C42···H4B^xi	3.0900
O2A···C8ⁱⁱⁱ	3.371 (3)	C42···H42^xi	3.0900
O2A···C14A^iv	3.337 (3)	H2A···C6^xi	2.8200
O2A···O1	3.210 (3)	H2B···C7^vii	2.7000
O2A···C7ⁱⁱⁱ	3.397 (4)	H2B···C3A	1.8000
O2B···O1	2.986 (14)	H2B···C4A	2.9500
O3B···C8ⁱⁱⁱ	3.280 (10)	H2B···H7^vii	2.2000
O1···H9ⁱⁱ	2.0700	H4A···O3A^viii	2.8400
O1···H9	2.8200	H4B···C8A^xi	2.9400
O2A···H8ⁱⁱⁱ	2.8400	H4B···C42^xi	3.0900
O2A···H31A	2.7000	H5···C5^x	3.0800
O2A···H14B	2.5900	H5···H5^x	2.2900
O2A···H14C	2.5300	H6···C14B^xii	3.0900
O2A···H14B^iv	2.3900	H6···H14D^xii	2.2800
O2A···H7ⁱⁱⁱ	2.8800	H6···C14A^xii	3.0900
O2B···H14E^v	2.8700	H7···O2A^ix	2.8800
O2B···H14F	2.5200	H7···H2B^vii	2.2000
O2B···H14E	2.1100	H8···O3B^ix	2.7400
O2B···H32A	2.6700	H8···O2A^ix	2.8400
O2B···H41ⁱ	2.7200	H8···H14C^ix	2.5200
O3A···H31B^vi	2.9100	H9···O1	2.8200
O3A···H14A^v	2.7600	H9···O1ⁱⁱ	2.0700
O3A···H4Aⁱ	2.8400	H14A···O3A^v	2.7600
O3B···H8ⁱⁱⁱ	2.7400	H14B···O2A	2.5900
N9···O1ⁱⁱ	2.883 (2)	H14B···O2A^iv	2.3900
N9···O1	2.941 (2)	H14C···O2A	2.5300
C1···C7^vii	3.410 (4)	H14C···C8ⁱⁱⁱ	2.8700
C2B···C7^vii	3.55 (2)	H14C···H8ⁱⁱⁱ	2.5200
C2B···C4A	2.55 (2)	H14D···C6^xiii	3.0000
C5···O1^viii	3.389 (3)	H14D···H6^xiii	2.2800
C7···C1^vii	3.410 (4)	H14E···O2B	2.1100
C7···C9A^vii	3.529 (4)	H14E···O2B^v	2.8700
C7···O2A^ix	3.397 (4)	H14E···H14E^v	2.3800
C7···C2B^vii	3.55 (2)	H14F···H32Bⁱ	1.9400
C8···C9A^vii	3.442 (3)	H14F···C3Bⁱ	2.8700
C8···O2A^ix	3.371 (3)	H14F···O2B	2.5200
C8···C41^vii	3.564 (3)	H31A···O2A	2.7000
C8···O3B^ix	3.280 (10)	H31A···C9A	3.0600
C8A···C8A^vii	3.490 (3)	H31B···O3A^vi	2.9100
C9A···C8^vii	3.442 (3)	H32A···O2B	2.6700
C9A···C7^vii	3.529 (4)	H32A···C4A	2.0100
C14A···O2A^iv	3.337 (3)	H32A···H4A	2.5300
C41···C8^vii	3.564 (3)	H32A···H4B	2.1200
C2B···H4B	3.0800	H32B···C4A	2.0100
C3B···H4B	2.0500	H32B···C14B^viii	2.8600
C3B···H4A	2.0500	H32B···H14F^viii	1.9400
C3B···H14F^viii	2.8700	H32B···H4A	2.1100
C5···H5^x	3.0800	H41···O2B^viii	2.7200
C6···H2A^xi	2.8200	H41···C3A	2.0500
C6···H14D^xii	3.0000	H41···H4B	1.5900
C7···H2B^vii	2.7000	H42···C3A	2.0500
C8···H14C^ix	2.8700	H42···H4A	1.5900
C8A···H4B^xi	2.9400	H42···C8A^xi	2.9400
C8A···H42^xi	2.9400	H42···C42^xi	3.0900

C13—O3A—C14A	116.0 (2)	C3A—C2A—H2A	107.00
C13—O3B—C14B	116.2 (7)	C13—C2A—H2A	107.00
C8A—N9—C9A	108.92 (17)	C13—C2B—H2B	99.00
C9A—N9—H9	126.00	C3B—C2B—H2B	99.00
C8A—N9—H9	126.00	C1—C2B—H2B	99.00
O1—C1—C2A	120.4 (2)	C2A—C3A—H31A	108.00
O1—C1—C9A	125.0 (2)	C2A—C3A—H31B	108.00
C2A—C1—C9A	114.4 (2)	H31A—C3A—H31B	107.00
O1—C1—C2B	119.4 (8)	C4A—C3A—H31A	108.00
C2B—C1—C9A	112.2 (8)	C4A—C3A—H31B	108.00
C1—C2A—C13	109.7 (2)	C2B—C3B—H32A	106.00
C3A—C2A—C13	113.9 (2)	C2B—C3B—H32B	106.00
C1—C2A—C3A	112.7 (2)	C4B—C3B—H32A	106.00
C3B—C2B—C13	126.8 (16)	C4B—C3B—H32B	106.00
C1—C2B—C3B	118.0 (14)	H32A—C3B—H32B	106.00
C1—C2B—C13	108.2 (14)	C3A—C4A—H4A	110.00
C2A—C3A—C4A	115.4 (2)	C41—C4A—H4A	110.00
C2B—C3B—C4B	126.3 (9)	C41—C4A—H4B	109.00
C3A—C4A—C41	110.6 (2)	C3A—C4A—H4B	110.00
C3B—C4B—C41	110.6 (2)	H4A—C4A—H4B	108.00
C6—C5—C42	119.7 (2)	C41—C4B—H42	109.00
C5—C6—C7	120.7 (3)	C3B—C4B—H41	110.00
C6—C7—C8	121.5 (3)	C3B—C4B—H42	110.00
C7—C8—C8A	117.8 (2)	H41—C4B—H42	108.00
N9—C8A—C8	130.6 (2)	C41—C4B—H41	110.00
N9—C8A—C42	107.85 (18)	C6—C5—H5	120.00
C8—C8A—C42	121.6 (2)	C42—C5—H5	120.00
N9—C9A—C1	125.8 (2)	C7—C6—H6	120.00
N9—C9A—C41	109.53 (18)	C5—C6—H6	120.00
C1—C9A—C41	124.7 (2)	C8—C7—H7	119.00
O2A—C13—O3A	121.7 (2)	C6—C7—H7	119.00
O2A—C13—C2A	121.2 (2)	C8A—C8—H8	121.00
O3A—C13—C2A	117.2 (2)	C7—C8—H8	121.00
O2B—C13—O3B	109.2 (9)	H14B—C14A—H14C	109.00
O2B—C13—C2B	102.2 (12)	H14A—C14A—H14C	110.00
O3B—C13—C2B	148.4 (10)	O3A—C14A—H14A	109.00
C4A—C41—C42	130.4 (2)	O3A—C14A—H14B	109.00
C9A—C41—C42	107.00 (19)	O3A—C14A—H14C	109.00
C4B—C41—C9A	122.59 (19)	H14A—C14A—H14B	109.00
C4B—C41—C42	130.4 (2)	O3B—C14B—H14D	109.00
C4A—C41—C9A	122.59 (19)	O3B—C14B—H14E	109.00
C5—C42—C41	134.6 (2)	O3B—C14B—H14F	109.00
C8A—C42—C41	106.70 (19)	H14D—C14B—H14E	110.00
C5—C42—C8A	118.7 (2)	H14D—C14B—H14F	109.00
C1—C2A—H2A	107.00	H14E—C14B—H14F	109.00

C14A—O3A—C13—C2A	179.7 (2)	C3A—C4A—C41—C9A	−19.1 (3)
C14A—O3A—C13—O2A	−0.1 (3)	C3A—C4A—C41—C42	159.3 (3)
C8A—N9—C9A—C1	177.0 (2)	C6—C5—C42—C41	−179.6 (3)
C8A—N9—C9A—C41	−0.7 (3)	C6—C5—C42—C8A	−1.3 (4)
C9A—N9—C8A—C8	−179.4 (2)	C42—C5—C6—C7	0.6 (4)
C9A—N9—C8A—C42	0.3 (2)	C5—C6—C7—C8	0.2 (4)
O1—C1—C9A—N9	−0.4 (4)	C6—C7—C8—C8A	−0.3 (4)
C2A—C1—C9A—C41	−8.4 (3)	C7—C8—C8A—C42	−0.4 (4)
O1—C1—C2A—C13	−24.7 (3)	C7—C8—C8A—N9	179.1 (2)
C9A—C1—C2A—C3A	32.3 (3)	N9—C8A—C42—C5	−178.5 (2)
C9A—C1—C2A—C13	160.4 (2)	N9—C8A—C42—C41	0.3 (3)
O1—C1—C9A—C41	177.0 (2)	C8—C8A—C42—C41	179.9 (2)
C2A—C1—C9A—N9	174.2 (2)	C8—C8A—C42—C5	1.2 (4)
O1—C1—C2A—C3A	−152.8 (2)	N9—C9A—C41—C4A	179.6 (2)
C1—C2A—C13—O3A	105.7 (3)	C1—C9A—C41—C42	−176.9 (2)
C3A—C2A—C13—O2A	53.0 (4)	N9—C9A—C41—C42	0.9 (3)
C3A—C2A—C13—O3A	−126.9 (3)	C1—C9A—C41—C4A	1.9 (4)
C13—C2A—C3A—C4A	−177.9 (2)	C4A—C41—C42—C5	−0.9 (5)
C1—C2A—C13—O2A	−74.4 (3)	C4A—C41—C42—C8A	−179.3 (2)
C1—C2A—C3A—C4A	−52.1 (3)	C9A—C41—C42—C5	177.8 (3)
C2A—C3A—C4A—C41	44.1 (3)	C9A—C41—C42—C8A	−0.7 (3)

Symmetry codes: (i) x+1, y, z; (ii) −x+1, −y+1, −z; (iii) x, y, z+1; (iv) −x+1, −y+1, −z+1; (v) −x+1, −y+2, −z+1; (vi) −x, −y+2, −z+1; (vii) −x, −y+1, −z; (viii) x−1, y, z; (ix) x, y, z−1; (x) −x−1, −y+2, −z; (xi) −x, −y+2, −z; (xii) x−1, y, z−1; (xiii) x+1, y, z+1.

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N9—H9···O1ⁱⁱ	0.87	2.07	2.883 (2)	155
C14A—H14B···O2A^iv	0.97	2.39	3.337 (3)	166

Symmetry codes: (ii) −x+1, −y+1, −z; (iv) −x+1, −y+1, −z+1.

Experimental details

Crystal data
Chemical formula	C₁₄H₁₃NO₃
M_r	243.25
Crystal system, space group	Triclinic, P1
Temperature (K)	203
a, b, c (Å)	6.9814 (12), 8.1303 (13), 10.780 (2)
α, β, γ (°)	88.575 (14), 76.881 (15), 79.367 (14)
V (Å³)	585.59 (18)
Z	2
Radiation type	Mo Kα
µ (mm⁻¹)	0.10
Crystal size (mm)	0.36 × 0.31 × 0.22

Data collection
Diffractometer	Oxford Diffraction Gemini
Absorption correction	Multi-scan (CrysAlis RED; Oxford Diffraction, 2007)
T_min, T_max	0.890, 1.000
No. of measured, independent and observed [I > 2σ(I)] reflections	6572, 3176, 1673
R_int	0.023
(sin θ/λ)_max (Å⁻¹)	0.717

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.067, 0.221, 1.11
No. of reflections	3176
No. of parameters	176
No. of restraints	6
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.80, −0.44

Computer programs: CrysAlis CCD (Oxford Diffraction, 2007), CrysAlis RED (Oxford Diffraction, 2007), CrysAlis RED, SHELXS97 (Sheldrick, 1997), SHELXL97 (Sheldrick, 1997), ORTEP-3 (Farrugia, 1997), PLATON (Spek, 2003).