Methyl 1-methyl-1H-indole-3-carboxyl­ate

The title indole derivative, C₁₁H₁₁NO₂, was synthesized from 1-methyl-1H-indole-3-carb­oxy­lic acid and methanol. The mol­ecule is planar as it is situated on a mirror plane present in the space group Pbcm. In the crystal, mol­ecules form three kinds of inter­molecular C—H...O hydrogen bonds, resulting in a sheet structure in the ab plane. Parallel sheets inter­act by C—H...π stacking, stabilizing the crystal packing.

Key indicators

• Single-crystal X-ray study
• T = 173 K
• Mean [sigma](C-C) = 0.004 Å
• R factor = 0.065
• wR factor = 0.208
• Data-to-parameter ratio = 13.4

checkCIF/PLATON results

No syntax errors found



Alert level B
DIFMN02_ALERT_2_B  The minimum difference density is < -0.1*ZMAX*1.00
            _refine_diff_density_min given =     -0.980
            Test value =     -0.800
PLAT098_ALERT_2_B Large Reported Min.  (Negative) Residual Density      -0.98 eA-3

Alert level C
DIFMN03_ALERT_1_C  The minimum difference density is < -0.1*ZMAX*0.75
            The relevant atom site should be identified.
DIFMX02_ALERT_1_C  The maximum difference density is > 0.1*ZMAX*0.75
            The relevant atom site should be identified.
PLAT029_ALERT_3_C _diffrn_measured_fraction_theta_full value Low .      0.979 Why?
PLAT097_ALERT_2_C Large Reported Max.  (Positive) Residual Density       0.72 eA-3
PLAT250_ALERT_2_C Large U3/U1 Ratio for Average U(i,j) Tensor ....        2.2 Note
PLAT906_ALERT_3_C Large K Value in the Analysis of Variance ......      3.214 Check
PLAT911_ALERT_3_C Missing FCF Refl Between Thmin & STh/L=    0.600          5 Report
PLAT918_ALERT_3_C Reflection(s) with I(obs) much Smaller I(calc) .          2 Check
PLAT939_ALERT_3_C Large Value of Not (SHELXL) Weight Optimized S .      12.78 Check
PLAT977_ALERT_2_C Check Negative Difference Density on H8               -0.91 eA-3
PLAT977_ALERT_2_C Check Negative Difference Density on H11A             -0.47 eA-3

Alert level G
PLAT072_ALERT_2_G SHELXL First  Parameter in WGHT  Unusually Large       0.13 Report
PLAT300_ALERT_4_G Atom Site Occupancy of H10B       Constrained at        0.5 Check
PLAT300_ALERT_4_G Atom Site Occupancy of H10C       Constrained at        0.5 Check
PLAT300_ALERT_4_G Atom Site Occupancy of H11B       Constrained at        0.5 Check
PLAT300_ALERT_4_G Atom Site Occupancy of H11C       Constrained at        0.5 Check
PLAT304_ALERT_4_G Non-Integer Number of Atoms in ...... Resd  1         12.50 Check
PLAT912_ALERT_4_G Missing # of FCF Reflections Above STh/L=  0.600         19 Note
PLAT913_ALERT_3_G Missing # of Very Strong Reflections in FCF ....          1 Note
PLAT978_ALERT_2_G Number C-C Bonds with Positive Residual Density.          7 Info

   0 ALERT level A = Most likely a serious problem - resolve or explain
   2 ALERT level B = A potentially serious problem, consider carefully
  11 ALERT level C = Check. Ensure it is not caused by an omission or oversight
   9 ALERT level G = General information/check it is not something unexpected

   2 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
   8 ALERT type 2 Indicator that the structure model may be wrong or deficient
   6 ALERT type 3 Indicator that the structure quality may be low
   6 ALERT type 4 Improvement, methodology, query or suggestion
   0 ALERT type 5 Informative message, check


checkCIF publication errors

Alert level A
PUBL024_ALERT_1_A The number of authors is greater than 5.
              Please specify the role of each of the co-authors
              for your paper.

   1 ALERT level A = Data missing that is essential or data in wrong format
   0 ALERT level G = General alerts. Data that may be required is missing

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Computing details

Data collection: APEX2 (Bruker, 2013); cell refinement: SAINT (Bruker, 2013); data reduction: SAINT (Bruker, 2013); program(s) used to solve structure: SHELXT2014 (Sheldrick, 2015a); program(s) used to refine structure: SHELXL2014 (Sheldrick, 2015b); molecular graphics: ORTEP-3 for Windows (Farrugia, 2012); software used to prepare material for publication: SHELXTL (Sheldrick, 2008).

Methyl 1-methyl-1H-indole-3-carboxylate

Crystal data

C11H11NO2	Dx = 1.346 Mg m^−3
Mr = 189.21	Mo Kα radiation, λ = 0.71073 Å
Orthorhombic, Pbcm	Cell parameters from 3337 reflections
a = 8.3019 (17) Å	θ = 2.5–27.5°
b = 16.628 (3) Å	µ = 0.09 mm^−1
c = 6.7622 (14) Å	T = 173 K
V = 933.5 (3) Å^3	Prism, colorless
Z = 4	0.50 × 0.24 × 0.17 mm
F(000) = 400

Data collection

Bruker APEXII CCD diffractometer	1142 independent reflections
Radiation source: fine-focus sealed tube	1053 reflections with I > 2σ(I)
Detector resolution: 8.3333 pixels mm^-1	Rint = 0.018
φ and ω scans	θmax = 27.5°, θmin = 2.5°
Absorption correction: multi-scan (SADABS; Bruker, 2013)	h = −10→10
Tmin = 0.88, Tmax = 0.98	k = −20→21
4700 measured reflections	l = −8→6

Refinement

Refinement on F^2	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F^2 > 2σ(F^2)] = 0.065	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.208	H-atom parameters constrained
S = 1.12	w = 1/[σ^2(Fo^2) + (0.1286P)^2 + 0.595P] where P = (Fo^2 + 2Fc^2)/3
1142 reflections	(Δ/σ)max < 0.001
85 parameters	Δρmax = 0.72 e Å^−3
0 restraints	Δρmin = −0.98 e Å^−3

Special details

Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes.

Refinement. All H atoms were located in difference Fourier maps. C-bound H atoms were constrained using a riding model [C—H = 0.95 Å and U_iso(H) = 1.2U_eq(C) for indole H atoms, and C—H = 0.98 Å and U_iso(H) = 1.5U_eq(C) for methyl H atoms].

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Ų)

	x	y	z	Uiso*/Ueq	Occ. (<1)
O1	0.6055 (2)	0.79479 (11)	0.75	0.0350 (6)
N1	0.6285 (3)	0.52415 (12)	0.75	0.0240 (5)
O2	0.8514 (2)	0.73850 (12)	0.75	0.0445 (7)
C8	0.7251 (3)	0.58886 (12)	0.75	0.0179 (5)
H8	0.8395	0.589	0.75	0.021*
C7	0.6279 (3)	0.65316 (14)	0.75	0.0233 (6)
C6	0.4631 (3)	0.62971 (13)	0.75	0.0225 (6)
C1	0.4691 (3)	0.54488 (14)	0.75	0.0228 (6)
C11	0.6944 (3)	0.44316 (16)	0.75	0.0290 (6)
H11A	0.606	0.4041	0.75	0.044*
H11B	0.7607	0.4354	0.6317	0.044*	0.5
H11C	0.7607	0.4354	0.8683	0.044*	0.5
C9	0.6900 (3)	0.73575 (15)	0.75	0.0254 (6)
C2	0.3304 (3)	0.49675 (16)	0.75	0.0284 (6)
H2	0.3362	0.4397	0.75	0.034*
C5	0.3130 (3)	0.66896 (16)	0.75	0.0277 (6)
H5	0.3062	0.726	0.75	0.033*
C4	0.1759 (3)	0.62199 (17)	0.75	0.0315 (7)
H4	0.0733	0.6473	0.75	0.038*
C3	0.1847 (3)	0.53694 (18)	0.75	0.0325 (7)
H3	0.0877	0.5066	0.75	0.039*
C10	0.9213 (4)	0.81809 (17)	0.75	0.0488 (10)
H10A	1.0391	0.8138	0.75	0.073*
H10B	0.8862	0.8472	0.6317	0.073*	0.5
H10C	0.8862	0.8472	0.8683	0.073*	0.5

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
O1	0.0301 (10)	0.0179 (9)	0.0569 (13)	0.0022 (7)	0	0
N1	0.0231 (11)	0.0175 (10)	0.0315 (11)	0.0010 (8)	0	0
O2	0.0240 (10)	0.0187 (10)	0.0908 (19)	−0.0017 (7)	0	0
C8	0.0178 (11)	0.0123 (10)	0.0235 (11)	0.0001 (7)	0	0
C7	0.0244 (12)	0.0181 (12)	0.0273 (12)	0.0022 (9)	0	0
C6	0.0251 (13)	0.0181 (11)	0.0244 (11)	−0.0001 (9)	0	0
C1	0.0232 (13)	0.0198 (11)	0.0253 (12)	0.0047 (9)	0	0
C11	0.0314 (13)	0.0181 (12)	0.0375 (14)	0.0056 (9)	0	0
C9	0.0244 (12)	0.0202 (13)	0.0315 (12)	0.0008 (8)	0	0
C2	0.0268 (13)	0.0223 (12)	0.0360 (13)	−0.0003 (10)	0	0
C5	0.0268 (13)	0.0219 (12)	0.0343 (13)	0.0049 (9)	0	0
C4	0.0236 (13)	0.0302 (14)	0.0407 (15)	0.0043 (10)	0	0
C3	0.0226 (12)	0.0300 (14)	0.0450 (16)	−0.0015 (10)	0	0
C10	0.0281 (14)	0.0199 (13)	0.098 (3)	−0.0039 (10)	0	0

Geometric parameters (Å, º)

O1—C9	1.206 (3)	C11—H11A	0.98
N1—C8	1.342 (3)	C11—H11B	0.98
N1—C1	1.368 (3)	C11—H11C	0.98
N1—C11	1.453 (3)	C2—C3	1.382 (4)
O2—C9	1.341 (3)	C2—H2	0.95
O2—C10	1.445 (3)	C5—C4	1.380 (4)
C8—C7	1.340 (3)	C5—H5	0.95
C8—H8	0.95	C4—C3	1.416 (4)
C7—C6	1.423 (3)	C4—H4	0.95
C7—C9	1.467 (3)	C3—H3	0.95
C6—C5	1.407 (3)	C10—H10A	0.98
C6—C1	1.412 (3)	C10—H10B	0.98
C1—C2	1.402 (4)	C10—H10C	0.98
C8—N1—C1	112.1 (2)	O1—C9—O2	123.6 (2)
C8—N1—C11	121.2 (2)	O1—C9—C7	123.9 (2)
C1—N1—C11	126.7 (2)	O2—C9—C7	112.5 (2)
C9—O2—C10	115.6 (2)	C3—C2—C1	116.3 (2)
C7—C8—N1	106.3 (2)	C3—C2—H2	121.9
C7—C8—H8	126.9	C1—C2—H2	121.9
N1—C8—H8	126.9	C4—C5—C6	117.9 (2)
C8—C7—C6	111.1 (2)	C4—C5—H5	121.1
C8—C7—C9	122.4 (2)	C6—C5—H5	121.1
C6—C7—C9	126.5 (2)	C5—C4—C3	121.5 (2)
C5—C6—C1	119.7 (2)	C5—C4—H4	119.3
C5—C6—C7	136.5 (2)	C3—C4—H4	119.3
C1—C6—C7	103.9 (2)	C2—C3—C4	121.9 (2)
N1—C1—C2	130.6 (2)	C2—C3—H3	119.0
N1—C1—C6	106.6 (2)	C4—C3—H3	119.0
C2—C1—C6	122.8 (2)	O2—C10—H10A	109.5
N1—C11—H11A	109.5	O2—C10—H10B	109.5
N1—C11—H11B	109.5	H10A—C10—H10B	109.5
H11A—C11—H11B	109.5	O2—C10—H10C	109.5
N1—C11—H11C	109.5	H10A—C10—H10C	109.5
H11A—C11—H11C	109.5	H10B—C10—H10C	109.5
H11B—C11—H11C	109.5
C1—N1—C8—C7	0	C7—C6—C1—C2	180.0
C11—N1—C8—C7	180.0	C10—O2—C9—O1	0
N1—C8—C7—C6	0	C10—O2—C9—C7	180.0
N1—C8—C7—C9	180.0	C8—C7—C9—O1	180.0
C8—C7—C6—C5	180.0	C6—C7—C9—O1	0
C9—C7—C6—C5	0	C8—C7—C9—O2	0
C8—C7—C6—C1	0	C6—C7—C9—O2	180.0
C9—C7—C6—C1	180.0	N1—C1—C2—C3	180.0
C8—N1—C1—C2	180.0	C6—C1—C2—C3	0
C11—N1—C1—C2	0	C1—C6—C5—C4	0
C8—N1—C1—C6	0	C7—C6—C5—C4	180.0
C11—N1—C1—C6	180.0	C6—C5—C4—C3	0
C5—C6—C1—N1	180.0	C1—C2—C3—C4	0
C7—C6—C1—N1	0	C5—C4—C3—C2	0
C5—C6—C1—C2	0

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
C4—H4···O2^i	0.95	2.39	3.318 (3)	167
C11—H11A···O1^ii	0.98	2.53	3.505 (4)	176
C2—H2···O1^ii	0.95	2.46	3.400 (3)	172
C11—H11B···Cg1^iii	0.98	2.69	3.412	131

Symmetry codes: (i) x−1, y, z; (ii) −x+1, y−1/2, −z+3/2; (iii) −x+1, −y+1, z−1/2.