Crystal structure of 4-(4b,8a-di­hydro-9H-pyrido[3,4-b]indol-1-yl)-7-methyl-2H-chromen-2-one

In the title compound, the dihedral angle between the mean planes of the coumarin and β-carboline ring systems is 63.8 (2)°. In the crystal, mol­ecules are linked via N—H...N hydrogen bonds, forming chains along the [010] direction.

Key indicators

• Single-crystal X-ray study
• T = 296 K
• Mean [sigma](C-C) = 0.004 Å
• R factor = 0.060
• wR factor = 0.166
• Data-to-parameter ratio = 12.5

checkCIF/PLATON results

No syntax errors found



Alert level C
PLAT340_ALERT_3_C Low Bond Precision on  C-C Bonds ...............    0.00409 Ang.
PLAT906_ALERT_3_C Large K value in the Analysis of Variance ......      7.816 Check
PLAT911_ALERT_3_C Missing # FCF Refl Between THmin & STh/L=  0.600          4 Report
PLAT978_ALERT_2_C Number C-C Bonds with Positive Residual Density.          0 Note

Alert level G
PLAT005_ALERT_5_G No Embedded Refinement Details found  in the CIF     Please Do !
PLAT007_ALERT_5_G Number of Unrefined Donor-H Atoms ..............          1 Report
PLAT882_ALERT_1_G Missing datum for _diffrn_reflns_av_unetI/netI .     Please Check
PLAT960_ALERT_3_G Number of Intensities with I  <   - 2*sig(I) ...          2 Check

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

   1 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
   1 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
   0 ALERT type 4 Improvement, methodology, query or suggestion
   2 ALERT type 5 Informative message, check

---

Computing details

Data collection: SMART (Bruker, 2012); cell refinement: SAINT (Bruker, 2012); data reduction: SAINT (Bruker, 2012); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL2014 (Sheldrick, 2015); molecular graphics: ORTEP-3 for Windows (Farrugia, 2012) and Mercury (Macrae et al., 2008); software used to prepare material for publication: WinGX (Farrugia, 2012) and PLATON (Spek, 2009).

4-(4b,8a-Dihydro-9H-pyrido[3,4-b]indol-1-yl)-7-methyl-2H-chromen-2-one

Crystal data

C21H14N2O2	F(000) = 680
Mr = 326.34	Dx = 1.415 Mg m^−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 1990 reflections
a = 10.6784 (8) Å	θ = 3.3–26.4°
b = 8.0954 (6) Å	µ = 0.09 mm^−1
c = 17.9032 (14) Å	T = 296 K
β = 98.105 (5)°	Block, colourless
V = 1532.2 (2) Å^3	0.20 × 0.15 × 0.10 mm
Z = 4

Data collection

Bruker SMART CCD area-detector diffractometer	2848 independent reflections
Radiation source: fine-focus sealed tube	1446 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.059
ω and φ scans	θmax = 25.5°, θmin = 1.9°
Absorption correction: multi-scan (SADABS; Bruker, 2012)	h = −12→11
Tmin = 0.941, Tmax = 0.971	k = −9→9
11601 measured reflections	l = −21→21

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)] = 0.060	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.166	H-atom parameters constrained
S = 0.94	w = 1/[σ^2(Fo^2) + (0.0799P)^2] where P = (Fo^2 + 2Fc^2)/3
2848 reflections	(Δ/σ)max < 0.001
227 parameters	Δρmax = 0.21 e Å^−3
0 restraints	Δρmin = −0.27 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.

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

	x	y	z	Uiso*/Ueq
O1	0.85044 (16)	0.1787 (2)	0.24656 (10)	0.0445 (6)
O2	0.87191 (18)	0.3169 (3)	0.35363 (12)	0.0602 (7)
N1	0.3818 (2)	0.2835 (3)	0.17822 (12)	0.0413 (7)
N2	0.4360 (2)	0.0447 (3)	0.35591 (12)	0.0407 (7)
H2	0.5149	0.0259	0.3707	0.049*
C1	0.7990 (3)	0.2565 (4)	0.30347 (17)	0.0429 (8)
C2	0.6635 (2)	0.2570 (3)	0.29733 (15)	0.0427 (8)
H2A	0.6264	0.3055	0.3359	0.051*
C3	0.5878 (2)	0.1912 (3)	0.23877 (15)	0.0341 (7)
C4	0.5774 (3)	0.0283 (4)	0.11849 (15)	0.0401 (8)
H4	0.4895	0.0273	0.1126	0.048*
C5	0.6389 (3)	−0.0500 (4)	0.06608 (15)	0.0459 (8)
H5	0.5921	−0.1047	0.0258	0.055*
C6	0.7705 (3)	−0.0486 (4)	0.07241 (15)	0.0427 (8)
C7	0.8384 (3)	0.0291 (4)	0.13369 (15)	0.0431 (8)
H7	0.9263	0.0302	0.1395	0.052*
C8	0.6443 (2)	0.1088 (3)	0.18005 (15)	0.0353 (7)
C9	0.7754 (2)	0.1051 (4)	0.18637 (15)	0.0370 (7)
C10	0.8380 (3)	−0.1277 (4)	0.01293 (17)	0.0635 (10)
H10A	0.924	−0.1509	0.0339	0.095*
H10B	0.8369	−0.0537	−0.0291	0.095*
H10C	0.7961	−0.2287	−0.0038	0.095*
C11	0.4475 (2)	0.2009 (4)	0.23601 (15)	0.0356 (7)
C12	0.2541 (3)	0.2974 (4)	0.17666 (16)	0.0464 (8)
H12	0.2093	0.3581	0.1376	0.056*
C13	0.1874 (3)	0.2280 (4)	0.22862 (17)	0.0449 (8)
H13	0.1	0.2388	0.2242	0.054*
C14	0.1087 (3)	0.0115 (4)	0.37782 (19)	0.0542 (9)
H14	0.0321	0.0482	0.3519	0.065*
C15	0.1115 (3)	−0.0820 (4)	0.44170 (19)	0.0595 (10)
H15	0.0361	−0.1107	0.4587	0.071*
C16	0.2255 (3)	−0.1345 (4)	0.48153 (18)	0.0589 (9)
H16	0.2248	−0.1961	0.5253	0.071*
C17	0.3403 (3)	−0.0978 (4)	0.45785 (16)	0.0489 (9)
H17	0.4166	−0.1329	0.4847	0.059*
C18	0.2223 (3)	0.0506 (4)	0.35234 (15)	0.0411 (8)
C19	0.3358 (3)	−0.0063 (4)	0.39225 (15)	0.0403 (7)
C20	0.2544 (2)	0.1410 (3)	0.28810 (16)	0.0370 (7)
C22	0.3865 (2)	0.1313 (3)	0.29183 (15)	0.0342 (7)

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
O1	0.0319 (11)	0.0588 (15)	0.0433 (12)	−0.0005 (10)	0.0069 (9)	−0.0029 (11)
O2	0.0450 (13)	0.0760 (18)	0.0575 (14)	−0.0050 (12)	−0.0001 (11)	−0.0134 (13)
N1	0.0356 (14)	0.0428 (17)	0.0454 (15)	0.0022 (12)	0.0056 (11)	0.0007 (13)
N2	0.0321 (13)	0.0503 (18)	0.0406 (14)	0.0004 (12)	0.0083 (11)	0.0003 (13)
C1	0.0423 (18)	0.044 (2)	0.0434 (18)	−0.0038 (16)	0.0090 (15)	−0.0018 (16)
C2	0.0376 (17)	0.049 (2)	0.0419 (18)	0.0018 (15)	0.0083 (14)	−0.0027 (16)
C3	0.0332 (15)	0.0306 (19)	0.0397 (16)	0.0001 (13)	0.0086 (13)	0.0041 (14)
C4	0.0372 (16)	0.043 (2)	0.0409 (17)	−0.0026 (15)	0.0071 (13)	0.0029 (15)
C5	0.048 (2)	0.048 (2)	0.0419 (18)	−0.0040 (16)	0.0066 (15)	0.0008 (16)
C6	0.055 (2)	0.037 (2)	0.0376 (17)	0.0076 (16)	0.0135 (15)	0.0056 (15)
C7	0.0359 (16)	0.049 (2)	0.0468 (18)	0.0071 (15)	0.0150 (14)	0.0058 (16)
C8	0.0385 (17)	0.0310 (19)	0.0373 (16)	−0.0013 (14)	0.0086 (13)	0.0032 (14)
C9	0.0311 (16)	0.041 (2)	0.0393 (17)	−0.0008 (14)	0.0060 (13)	0.0051 (15)
C10	0.070 (2)	0.071 (3)	0.054 (2)	0.0156 (19)	0.0223 (17)	−0.0037 (19)
C11	0.0333 (16)	0.036 (2)	0.0382 (16)	−0.0008 (14)	0.0086 (13)	−0.0025 (14)
C12	0.0383 (18)	0.050 (2)	0.0500 (19)	0.0041 (16)	0.0011 (15)	−0.0005 (16)
C13	0.0320 (16)	0.045 (2)	0.058 (2)	0.0013 (15)	0.0074 (15)	−0.0065 (17)
C14	0.0461 (19)	0.048 (2)	0.074 (2)	0.0008 (17)	0.0276 (17)	−0.0005 (19)
C15	0.064 (2)	0.051 (2)	0.073 (2)	−0.0048 (19)	0.0414 (19)	−0.001 (2)
C16	0.078 (2)	0.049 (2)	0.056 (2)	−0.006 (2)	0.0313 (19)	0.0005 (18)
C17	0.059 (2)	0.041 (2)	0.0487 (19)	0.0011 (17)	0.0127 (16)	0.0001 (16)
C18	0.0375 (17)	0.037 (2)	0.0509 (19)	−0.0006 (15)	0.0157 (14)	−0.0048 (16)
C19	0.0418 (17)	0.0379 (19)	0.0440 (18)	−0.0030 (15)	0.0157 (14)	−0.0038 (15)
C20	0.0310 (16)	0.036 (2)	0.0445 (17)	0.0027 (14)	0.0093 (13)	−0.0075 (15)
C22	0.0324 (16)	0.033 (2)	0.0372 (17)	0.0017 (13)	0.0059 (13)	−0.0078 (14)

Geometric parameters (Å, º)

O1—C1	1.377 (3)	C8—C9	1.389 (3)
O1—C9	1.383 (3)	C10—H10A	0.96
O2—C1	1.206 (3)	C10—H10B	0.96
N1—C11	1.344 (3)	C10—H10C	0.96
N1—C12	1.365 (3)	C11—C22	1.388 (3)
N2—C22	1.384 (3)	C12—C13	1.369 (4)
N2—C19	1.391 (3)	C12—H12	0.93
N2—H2	0.86	C13—C20	1.388 (4)
C1—C2	1.435 (4)	C13—H13	0.93
C2—C3	1.341 (3)	C14—C15	1.368 (4)
C2—H2A	0.93	C14—C18	1.392 (4)
C3—C8	1.447 (3)	C14—H14	0.93
C3—C11	1.494 (3)	C15—C16	1.388 (4)
C4—C5	1.374 (4)	C15—H15	0.93
C4—C8	1.388 (3)	C16—C17	1.385 (4)
C4—H4	0.93	C16—H16	0.93
C5—C6	1.394 (4)	C17—C19	1.384 (4)
C5—H5	0.93	C17—H17	0.93
C6—C7	1.379 (4)	C18—C19	1.396 (4)
C6—C10	1.510 (4)	C18—C20	1.445 (4)
C7—C9	1.378 (4)	C20—C22	1.405 (3)
C7—H7	0.93
C1—O1—C9	121.7 (2)	H10A—C10—H10C	109.5
C11—N1—C12	117.9 (2)	H10B—C10—H10C	109.5
C22—N2—C19	108.0 (2)	N1—C11—C22	120.6 (2)
C22—N2—H2	126	N1—C11—C3	117.7 (2)
C19—N2—H2	126	C22—C11—C3	121.7 (2)
O2—C1—O1	117.0 (3)	C13—C12—N1	124.5 (3)
O2—C1—C2	126.4 (3)	C13—C12—H12	117.8
O1—C1—C2	116.6 (3)	N1—C12—H12	117.8
C3—C2—C1	123.3 (3)	C12—C13—C20	117.9 (3)
C3—C2—H2A	118.4	C12—C13—H13	121
C1—C2—H2A	118.4	C20—C13—H13	121
C2—C3—C8	119.0 (2)	C15—C14—C18	118.8 (3)
C2—C3—C11	119.7 (3)	C15—C14—H14	120.6
C8—C3—C11	121.3 (2)	C18—C14—H14	120.6
C5—C4—C8	121.1 (3)	C14—C15—C16	120.9 (3)
C5—C4—H4	119.4	C14—C15—H15	119.6
C8—C4—H4	119.4	C16—C15—H15	119.6
C4—C5—C6	121.0 (3)	C17—C16—C15	121.8 (3)
C4—C5—H5	119.5	C17—C16—H16	119.1
C6—C5—H5	119.5	C15—C16—H16	119.1
C7—C6—C5	118.6 (3)	C16—C17—C19	116.6 (3)
C7—C6—C10	120.3 (3)	C16—C17—H17	121.7
C5—C6—C10	121.0 (3)	C19—C17—H17	121.7
C6—C7—C9	119.7 (3)	C14—C18—C19	119.5 (3)
C6—C7—H7	120.1	C14—C18—C20	133.8 (3)
C9—C7—H7	120.1	C19—C18—C20	106.7 (2)
C9—C8—C4	117.0 (3)	C17—C19—N2	128.3 (3)
C9—C8—C3	118.0 (2)	C17—C19—C18	122.3 (3)
C4—C8—C3	124.9 (2)	N2—C19—C18	109.4 (2)
C7—C9—O1	116.1 (2)	C13—C20—C22	118.0 (3)
C7—C9—C8	122.5 (3)	C13—C20—C18	135.5 (3)
O1—C9—C8	121.4 (2)	C22—C20—C18	106.4 (2)
C6—C10—H10A	109.5	C11—C22—N2	129.7 (2)
C6—C10—H10B	109.5	C11—C22—C20	120.9 (3)
H10A—C10—H10B	109.5	N2—C22—C20	109.4 (2)
C6—C10—H10C	109.5
C9—O1—C1—O2	179.9 (2)	C11—N1—C12—C13	−2.4 (4)
C9—O1—C1—C2	0.2 (4)	N1—C12—C13—C20	1.7 (4)
O2—C1—C2—C3	178.1 (3)	C18—C14—C15—C16	1.3 (5)
O1—C1—C2—C3	−2.2 (4)	C14—C15—C16—C17	−1.2 (5)
C1—C2—C3—C8	2.8 (4)	C15—C16—C17—C19	−0.2 (4)
C1—C2—C3—C11	−178.5 (3)	C15—C14—C18—C19	0.1 (4)
C8—C4—C5—C6	−1.1 (4)	C15—C14—C18—C20	178.5 (3)
C4—C5—C6—C7	1.8 (4)	C16—C17—C19—N2	−179.0 (3)
C4—C5—C6—C10	−177.1 (3)	C16—C17—C19—C18	1.6 (4)
C5—C6—C7—C9	−0.9 (4)	C22—N2—C19—C17	179.2 (3)
C10—C6—C7—C9	178.0 (3)	C22—N2—C19—C18	−1.3 (3)
C5—C4—C8—C9	−0.5 (4)	C14—C18—C19—C17	−1.6 (4)
C5—C4—C8—C3	−178.6 (3)	C20—C18—C19—C17	179.7 (3)
C2—C3—C8—C9	−1.4 (4)	C14—C18—C19—N2	178.9 (3)
C11—C3—C8—C9	179.8 (2)	C20—C18—C19—N2	0.1 (3)
C2—C3—C8—C4	176.6 (3)	C12—C13—C20—C22	0.7 (4)
C11—C3—C8—C4	−2.2 (4)	C12—C13—C20—C18	−179.2 (3)
C6—C7—C9—O1	179.3 (2)	C14—C18—C20—C13	2.6 (6)
C6—C7—C9—C8	−0.8 (4)	C19—C18—C20—C13	−178.9 (3)
C1—O1—C9—C7	−179.1 (2)	C14—C18—C20—C22	−177.4 (3)
C1—O1—C9—C8	1.0 (4)	C19—C18—C20—C22	1.1 (3)
C4—C8—C9—C7	1.5 (4)	N1—C11—C22—N2	−178.8 (2)
C3—C8—C9—C7	179.7 (2)	C3—C11—C22—N2	−0.5 (4)
C4—C8—C9—O1	−178.6 (2)	N1—C11—C22—C20	2.0 (4)
C3—C8—C9—O1	−0.4 (4)	C3—C11—C22—C20	−179.7 (2)
C12—N1—C11—C22	0.4 (4)	C19—N2—C22—C11	−177.3 (3)
C12—N1—C11—C3	−177.9 (2)	C19—N2—C22—C20	2.0 (3)
C2—C3—C11—N1	118.4 (3)	C13—C20—C22—C11	−2.5 (4)
C8—C3—C11—N1	−62.9 (3)	C18—C20—C22—C11	177.4 (2)
C2—C3—C11—C22	−60.0 (4)	C13—C20—C22—N2	178.1 (2)
C8—C3—C11—C22	118.8 (3)	C18—C20—C22—N2	−1.9 (3)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
N2—H2···N1^i	0.86	2.47	2.994 (3)	120

Symmetry code: (i) −x+1, y−1/2, −z+1/2.