Succinimidyl 7-meth­oxy-2H-chromene-3-carboxyl­ate

In the title mol­ecule, C₁₅H₁₁NO₇, the dihedral angle between the coumarin unit and the succinimide unit is 72.36 (4)°. The crystal structure is stabilized by weak inter­molecular C—H...O hydrogen bonds and π–π stacking inter­actions.

Key indicators

• Single-crystal X-ray study
• T = 150 K
• Mean [sigma](C-C) = 0.003 Å
• R factor = 0.055
• wR factor = 0.149
• Data-to-parameter ratio = 15.1

checkCIF/PLATON results

No syntax errors found



Alert level B
PLAT432_ALERT_2_B Short Inter X...Y Contact  O3     ..  C15     ..       2.85 Ang.
PLAT432_ALERT_2_B Short Inter X...Y Contact  C1     ..  C1      ..       3.09 Ang.

Alert level C
ABSTM02_ALERT_3_C  The ratio of expected to reported Tmax/Tmin(RR') is < 0.90
            Tmin and Tmax reported:      0.838     0.996
            Tmin(prime) and Tmax expected:      0.963     0.983
            RR(prime) =      0.859
            Please check that your absorption correction is appropriate.
PLAT061_ALERT_3_C Tmax/Tmin Range Test RR' too Large .............       0.86
PLAT062_ALERT_4_C Rescale T(min) & T(max) by .....................       0.99

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

   0 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
   2 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

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Computing details

Data collection: COLLECT (Nonius, 2002); cell refinement: DENZO-SMN (Otwinowski & Minor, 1997); data reduction: DENZO-SMN; program(s) used to solve structure: SIR92 (Altomare et al., 1994); program(s) used to refine structure: SHELXTL (Sheldrick, 2001); molecular graphics: SHELXTL and PLATON (Spek, 2003); software used to prepare material for publication: SHELXTL.

Succinimidyl 7-methoxy-2H-chromene-3-carboxylate

Crystal data

C15H11NO7	F(000) = 656
Mr = 317.25	Dx = 1.511 Mg m^−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 8788 reflections
a = 8.4164 (6) Å	θ = 2.6–27.5°
b = 19.4304 (13) Å	µ = 0.12 mm^−1
c = 8.5521 (6) Å	T = 150 K
β = 94.475 (4)°	Block, colourless
V = 1394.30 (17) Å^3	0.30 × 0.20 × 0.14 mm
Z = 4

Data collection

Bruker–Nonius KappaCCD diffractometer	3179 independent reflections
Radiation source: fine-focus sealed tube	1763 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.061
Detector resolution: 9 pixels mm^-1	θmax = 27.5°, θmin = 2.6°
φ scans and ω scans with κ offsets	h = −10→10
Absorption correction: multi-scan (SORTAV; Blessing, 1995)	k = −25→25
Tmin = 0.838, Tmax = 0.996	l = −10→11
8788 measured reflections

Refinement

Refinement on F^2	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F^2 > 2σ(F^2)] = 0.055	H-atom parameters constrained
wR(F^2) = 0.149	w = 1/[σ^2(Fo^2) + (0.0719P)^2] where P = (Fo^2 + 2Fc^2)/3
S = 1.01	(Δ/σ)max = 0.001
3179 reflections	Δρmax = 0.23 e Å^−3
210 parameters	Δρmin = −0.18 e Å^−3
0 restraints	Extinction correction: SHELXTL, Fc^*=kFc[1+0.001xFc^2λ^3/sin(2θ)]^-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.017 (4)

Special details

Experimental. ¹H spectra were referenced to tetramethylsilane (TMS, 0 p.p.m.) and ¹³C spectra were referenced to solvent C atoms (77.24 p.p.m. for CDCl₃). ¹H NMR (300 MHz, CDCl₃): δ 2.90 (s, 4H), 3.95 (s, 3H), 6.85 (s, 1H), 6.95 (d, J = 9.0 Hz, 1H), 7.57 (d, J = 9.0 Hz, 1H), 8.76 (s, 1H).

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

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 (Ų)

	x	y	z	Uiso*/Ueq
O1	0.29798 (16)	0.47164 (6)	0.55790 (15)	0.0408 (4)
O2	0.46859 (18)	0.52232 (7)	0.72952 (17)	0.0469 (4)
O3	0.5366 (2)	0.66221 (7)	0.68084 (18)	0.0548 (5)
O4	0.43240 (19)	0.70287 (7)	0.44688 (17)	0.0519 (4)
O5	−0.10188 (19)	0.35835 (9)	0.2271 (2)	0.0641 (5)
O6	0.3065 (2)	0.82010 (9)	0.57949 (19)	0.0679 (5)
O7	0.7516 (2)	0.72553 (8)	0.39624 (19)	0.0626 (5)
N1	0.5167 (2)	0.76237 (9)	0.4866 (2)	0.0504 (5)
C1	0.3819 (2)	0.52968 (10)	0.6121 (2)	0.0390 (5)
C2	0.3568 (2)	0.59169 (10)	0.5172 (2)	0.0392 (5)
C3	0.2502 (2)	0.59193 (10)	0.3891 (2)	0.0424 (5)
H3A	0.2371	0.6325	0.3275	0.051*
C4	0.1582 (2)	0.53282 (11)	0.3457 (2)	0.0415 (5)
C5	0.0391 (3)	0.53177 (13)	0.2209 (3)	0.0513 (6)
H5A	0.0178	0.5720	0.1598	0.062*
C6	−0.0459 (3)	0.47319 (13)	0.1873 (3)	0.0549 (6)
H6A	−0.1285	0.4732	0.1050	0.066*
C7	−0.0120 (3)	0.41317 (12)	0.2736 (3)	0.0508 (6)
C8	0.1059 (2)	0.41212 (11)	0.3971 (2)	0.0454 (5)
H8A	0.1298	0.3713	0.4555	0.055*
C9	0.1870 (2)	0.47270 (10)	0.4316 (2)	0.0396 (5)
C10	−0.0664 (3)	0.29387 (14)	0.3013 (3)	0.0707 (8)
H10A	−0.1416	0.2590	0.2580	0.106*
H10B	−0.0757	0.2982	0.4144	0.106*
H10C	0.0424	0.2801	0.2825	0.106*
C11	0.4519 (3)	0.65274 (10)	0.5645 (3)	0.0425 (5)
C12	0.4437 (4)	0.81928 (12)	0.5463 (3)	0.0562 (6)
C13	0.5670 (4)	0.87500 (12)	0.5562 (3)	0.0678 (8)
H13A	0.5823	0.8934	0.6642	0.081*
H13B	0.5351	0.9132	0.4837	0.081*
C14	0.7199 (3)	0.84069 (12)	0.5089 (3)	0.0650 (7)
H14A	0.7653	0.8671	0.4239	0.078*
H14B	0.8002	0.8384	0.5997	0.078*
C15	0.6744 (3)	0.76976 (12)	0.4535 (3)	0.0527 (6)

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
O1	0.0405 (8)	0.0396 (8)	0.0421 (8)	−0.0019 (6)	0.0024 (6)	0.0028 (6)
O2	0.0512 (9)	0.0448 (8)	0.0439 (8)	−0.0016 (7)	−0.0008 (7)	0.0031 (7)
O3	0.0712 (11)	0.0457 (9)	0.0469 (9)	−0.0082 (8)	0.0018 (8)	0.0022 (7)
O4	0.0686 (11)	0.0385 (8)	0.0487 (9)	−0.0085 (7)	0.0051 (7)	0.0058 (7)
O5	0.0547 (11)	0.0771 (12)	0.0609 (10)	−0.0162 (9)	0.0068 (8)	−0.0184 (9)
O6	0.0850 (14)	0.0697 (11)	0.0501 (10)	0.0149 (10)	0.0114 (9)	0.0014 (8)
O7	0.0721 (12)	0.0559 (10)	0.0614 (10)	−0.0013 (9)	0.0159 (9)	0.0001 (9)
N1	0.0695 (14)	0.0333 (9)	0.0499 (11)	−0.0061 (9)	0.0131 (9)	0.0001 (9)
C1	0.0402 (12)	0.0353 (11)	0.0422 (12)	0.0011 (9)	0.0079 (9)	−0.0017 (9)
C2	0.0422 (12)	0.0388 (11)	0.0379 (11)	0.0028 (9)	0.0113 (9)	0.0020 (9)
C3	0.0425 (12)	0.0433 (11)	0.0428 (12)	0.0070 (9)	0.0121 (10)	0.0054 (10)
C4	0.0366 (12)	0.0500 (13)	0.0389 (11)	0.0038 (9)	0.0089 (9)	0.0027 (10)
C5	0.0405 (13)	0.0684 (15)	0.0453 (13)	0.0045 (11)	0.0052 (10)	0.0047 (11)
C6	0.0406 (13)	0.0843 (18)	0.0399 (12)	−0.0012 (12)	0.0023 (10)	−0.0031 (12)
C7	0.0409 (13)	0.0679 (15)	0.0448 (13)	−0.0098 (11)	0.0113 (10)	−0.0138 (12)
C8	0.0429 (13)	0.0498 (13)	0.0446 (12)	−0.0026 (10)	0.0093 (10)	−0.0039 (10)
C9	0.0331 (11)	0.0502 (12)	0.0362 (11)	0.0015 (9)	0.0068 (9)	−0.0023 (10)
C10	0.0625 (17)	0.0715 (17)	0.0796 (18)	−0.0202 (14)	0.0160 (14)	−0.0266 (16)
C11	0.0512 (13)	0.0384 (12)	0.0394 (12)	0.0040 (10)	0.0133 (10)	0.0039 (10)
C12	0.0844 (19)	0.0472 (13)	0.0377 (12)	0.0036 (13)	0.0088 (12)	0.0026 (11)
C13	0.116 (2)	0.0423 (13)	0.0456 (14)	−0.0076 (14)	0.0105 (14)	−0.0033 (11)
C14	0.090 (2)	0.0537 (15)	0.0511 (14)	−0.0188 (13)	0.0060 (13)	0.0017 (12)
C15	0.0682 (17)	0.0467 (13)	0.0441 (13)	−0.0101 (12)	0.0092 (11)	0.0041 (11)

Geometric parameters (Å, º)

O1—C9	1.372 (2)	C4—C5	1.406 (3)
O1—C1	1.391 (2)	C5—C6	1.363 (3)
O2—C1	1.203 (2)	C5—H5A	0.9500
O3—C11	1.192 (2)	C6—C7	1.398 (3)
O4—N1	1.385 (2)	C6—H6A	0.9500
O4—C11	1.401 (2)	C7—C8	1.392 (3)
O5—C7	1.349 (3)	C8—C9	1.380 (3)
O5—C10	1.425 (3)	C8—H8A	0.9500
O6—C12	1.211 (3)	C10—H10A	0.9800
O7—C15	1.205 (3)	C10—H10B	0.9800
N1—C12	1.382 (3)	C10—H10C	0.9800
N1—C15	1.385 (3)	C12—C13	1.498 (4)
C1—C2	1.459 (3)	C13—C14	1.532 (4)
C2—C3	1.361 (3)	C13—H13A	0.9900
C2—C11	1.470 (3)	C13—H13B	0.9900
C3—C4	1.418 (3)	C14—C15	1.497 (3)
C3—H3A	0.9500	C14—H14A	0.9900
C4—C9	1.391 (3)	C14—H14B	0.9900
C9—O1—C1	123.15 (15)	O1—C9—C8	116.73 (18)
N1—O4—C11	112.04 (16)	O1—C9—C4	120.53 (18)
C7—O5—C10	118.0 (2)	C8—C9—C4	122.7 (2)
C12—N1—O4	121.6 (2)	O5—C10—H10A	109.5
C12—N1—C15	116.9 (2)	O5—C10—H10B	109.5
O4—N1—C15	121.13 (17)	H10A—C10—H10B	109.5
O2—C1—O1	116.15 (17)	O5—C10—H10C	109.5
O2—C1—C2	127.92 (19)	H10A—C10—H10C	109.5
O1—C1—C2	115.91 (18)	H10B—C10—H10C	109.5
C3—C2—C1	120.55 (19)	O3—C11—O4	121.39 (19)
C3—C2—C11	121.98 (19)	O3—C11—C2	129.19 (19)
C1—C2—C11	117.46 (18)	O4—C11—C2	109.41 (18)
C2—C3—C4	121.33 (19)	O6—C12—N1	123.8 (2)
C2—C3—H3A	119.3	O6—C12—C13	130.3 (2)
C4—C3—H3A	119.3	N1—C12—C13	105.9 (2)
C9—C4—C5	118.2 (2)	C12—C13—C14	105.3 (2)
C9—C4—C3	118.23 (19)	C12—C13—H13A	110.7
C5—C4—C3	123.5 (2)	C14—C13—H13A	110.7
C6—C5—C4	120.2 (2)	C12—C13—H13B	110.7
C6—C5—H5A	119.9	C14—C13—H13B	110.7
C4—C5—H5A	119.9	H13A—C13—H13B	108.8
C5—C6—C7	120.2 (2)	C15—C14—C13	106.5 (2)
C5—C6—H6A	119.9	C15—C14—H14A	110.4
C7—C6—H6A	119.9	C13—C14—H14A	110.4
O5—C7—C8	124.3 (2)	C15—C14—H14B	110.4
O5—C7—C6	114.6 (2)	C13—C14—H14B	110.4
C8—C7—C6	121.1 (2)	H14A—C14—H14B	108.6
C9—C8—C7	117.4 (2)	O7—C15—N1	124.4 (2)
C9—C8—H8A	121.3	O7—C15—C14	130.7 (2)
C7—C8—H8A	121.3	N1—C15—C14	104.9 (2)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
C3—H3A···O6^i	0.95	2.43	3.218 (2)	141
C8—H8A···O7^ii	0.95	2.44	3.374 (3)	168
C10—H10A···O6^iii	0.98	2.55	3.217 (3)	125
C13—H13B···O2^i	0.99	2.53	3.480 (3)	160

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