Succinimidyl 7-(diethyl­amino)-2-oxo-2H-chromene-3-carboxyl­ate chloro­form solvate

In the title mol­ecular structure, C₁₈H₁₈N₂O₆·CHCl₃, the dihedral angle between the two fused, essentially planar, six-membered rings is 5.4 (2)°. In the crystal structure, weak inter­molecular C—H...O hydrogen bonds and π–π stacking inter­actions connect mol­ecules into two-dimensional layers.

Key indicators

• Single-crystal X-ray study
• T = 150 K
• Mean [sigma](C-C) = 0.008 Å
• R factor = 0.070
• wR factor = 0.208
• Data-to-parameter ratio = 13.2

checkCIF/PLATON results

No syntax errors found



Alert level B
PLAT431_ALERT_2_B Short Inter HL..A Contact  Cl1    ..  O5      ..       2.95 Ang.

Alert level C
ABSTM02_ALERT_3_C  The ratio of expected to reported Tmax/Tmin(RR') is < 0.90
            Tmin and Tmax reported:      0.746     0.964
            Tmin(prime) and Tmax expected:      0.864     0.962
            RR(prime) =      0.862
            Please check that your absorption correction is appropriate.
RINTA01_ALERT_3_C  The value of Rint is greater than 0.10
            Rint given   0.126
PLAT020_ALERT_3_C The value of Rint is greater than 0.10 .........       0.13
PLAT029_ALERT_3_C _diffrn_measured_fraction_theta_full Low .......       0.97
PLAT061_ALERT_3_C Tmax/Tmin Range Test RR' too Large .............       0.86
PLAT244_ALERT_4_C Low   'Solvent' Ueq as Compared to Neighbors for        C1S
PLAT340_ALERT_3_C Low Bond Precision on C-C bonds (x 1000) Ang ...          8
PLAT720_ALERT_4_C Number of Unusual/Non-Standard Label(s) ........          1

   0 ALERT level A = In general: serious problem
   1 ALERT level B = Potentially serious problem
   8 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
   1 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
   2 ALERT type 4 Improvement, methodology, query or suggestion

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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; software used to prepare material for publication: SHELXTL.

Succinimidyl 7-(diethylamino)-2-oxo-2H-chromene-3-carboxylate chloroform solvate

Crystal data

C18H18N2O6·CHCl3	F(000) = 1968
Mr = 477.71	Dx = 1.526 Mg m^−3
Monoclinic, C2/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -C 2yc	Cell parameters from 3598 reflections
a = 19.601 (3) Å	θ = 2.6–25.2°
b = 9.3170 (14) Å	µ = 0.48 mm^−1
c = 22.807 (3) Å	T = 150 K
β = 93.429 (9)°	Needle, yellow
V = 4157.6 (10) Å^3	0.30 × 0.16 × 0.08 mm
Z = 8

Data collection

Bruker–Nonius KappaCCD diffractometer	3598 independent reflections
Radiation source: fine-focus sealed tube	2151 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.126
Detector resolution: 9 pixels mm^-1	θmax = 25.2°, θmin = 2.6°
φ scans and ω scans with κ offsets	h = −23→23
Absorption correction: multi-scan (SORTAV; Blessing, 1995)	k = −11→11
Tmin = 0.746, Tmax = 0.964	l = −2→27
11417 measured reflections

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)] = 0.070	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.209	H-atom parameters constrained
S = 1.05	w = 1/[σ^2(Fo^2) + (0.094P)^2 + 7.3572P] where P = (Fo^2 + 2Fc^2)/3
3598 reflections	(Δ/σ)max < 0.001
272 parameters	Δρmax = 0.30 e Å^−3
0 restraints	Δρmin = −0.39 e Å^−3

Special details

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	0.70586 (19)	0.7105 (4)	0.58743 (15)	0.0344 (9)
O2	0.7460 (2)	0.5924 (5)	0.66551 (17)	0.0429 (10)
O3	0.7266 (2)	0.1982 (4)	0.57400 (17)	0.0419 (10)
O4	0.7382 (2)	0.3020 (4)	0.66391 (16)	0.0376 (10)
O5	0.6284 (2)	0.1207 (5)	0.6870 (2)	0.0544 (12)
O6	0.8582 (2)	0.1372 (5)	0.66877 (18)	0.0422 (10)
N1	0.5948 (2)	0.9878 (6)	0.4336 (2)	0.0371 (12)
N2	0.7441 (2)	0.1613 (5)	0.6837 (2)	0.0368 (12)
C1	0.7237 (3)	0.5819 (6)	0.6155 (3)	0.0350 (14)
C2	0.7137 (3)	0.4526 (6)	0.5805 (2)	0.0350 (14)
C3	0.6884 (3)	0.4614 (6)	0.5234 (2)	0.0350 (14)
H3A	0.6849	0.3764	0.5004	0.042*
C4	0.6675 (3)	0.5925 (6)	0.4978 (2)	0.0314 (13)
C5	0.6346 (3)	0.6052 (7)	0.4418 (2)	0.0364 (14)
H5A	0.6281	0.5219	0.4181	0.044*
C6	0.6115 (3)	0.7343 (7)	0.4204 (2)	0.0368 (14)
H6A	0.5894	0.7395	0.3823	0.044*
C7	0.6203 (3)	0.8612 (6)	0.4548 (2)	0.0330 (13)
C8	0.6551 (3)	0.8508 (6)	0.5111 (2)	0.0330 (13)
H8A	0.6635	0.9340	0.5345	0.040*
C9	0.6764 (3)	0.7182 (6)	0.5310 (2)	0.0313 (13)
C10	0.5467 (3)	0.9957 (7)	0.3813 (2)	0.0390 (14)
H10A	0.5156	1.0784	0.3855	0.047*
H10B	0.5184	0.9076	0.3792	0.047*
C11	0.5823 (3)	1.0117 (8)	0.3247 (3)	0.0486 (17)
H11A	0.5482	1.0150	0.2915	0.073*
H11B	0.6129	0.9297	0.3200	0.073*
H11C	0.6091	1.1006	0.3259	0.073*
C12	0.6105 (3)	1.1242 (6)	0.4639 (3)	0.0365 (14)
H12A	0.6078	1.2032	0.4349	0.044*
H12B	0.6579	1.1208	0.4815	0.044*
C13	0.5617 (3)	1.1563 (7)	0.5122 (3)	0.0424 (15)
H13A	0.5745	1.2477	0.5312	0.064*
H13B	0.5646	1.0792	0.5415	0.064*
H13C	0.5148	1.1627	0.4950	0.064*
C14	0.7267 (3)	0.3071 (7)	0.6031 (3)	0.0378 (15)
C15	0.6863 (3)	0.0776 (7)	0.6927 (3)	0.0407 (15)
C16	0.7129 (3)	−0.0671 (6)	0.7111 (3)	0.0368 (14)
H16A	0.6926	−0.1426	0.6849	0.044*
H16B	0.7017	−0.0884	0.7519	0.044*
C17	0.7906 (3)	−0.0611 (6)	0.7065 (3)	0.0387 (15)
H17A	0.8145	−0.0771	0.7454	0.046*
H17B	0.8056	−0.1350	0.6788	0.046*
C18	0.8051 (3)	0.0865 (7)	0.6842 (2)	0.0382 (14)
Cl1	0.55238 (10)	0.3932 (2)	0.67495 (9)	0.0681 (6)
Cl2	0.56500 (10)	0.6982 (2)	0.69534 (9)	0.0686 (6)
Cl3	0.52235 (9)	0.5908 (2)	0.58048 (8)	0.0582 (5)
C1S	0.5184 (3)	0.5636 (7)	0.6572 (3)	0.0490 (17)
H1SA	0.4696	0.5676	0.6678	0.059*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
O1	0.038 (2)	0.036 (2)	0.028 (2)	0.0064 (19)	−0.0053 (17)	0.0005 (17)
O2	0.048 (2)	0.042 (3)	0.037 (2)	0.003 (2)	−0.009 (2)	0.0002 (19)
O3	0.046 (3)	0.037 (3)	0.042 (2)	0.002 (2)	−0.0033 (19)	−0.004 (2)
O4	0.047 (2)	0.030 (2)	0.035 (2)	0.0035 (19)	−0.0034 (18)	0.0039 (17)
O5	0.037 (3)	0.055 (3)	0.071 (3)	0.008 (2)	0.007 (2)	0.014 (2)
O6	0.034 (2)	0.044 (3)	0.048 (3)	−0.003 (2)	0.0006 (19)	0.001 (2)
N1	0.037 (3)	0.042 (3)	0.031 (2)	0.003 (2)	−0.007 (2)	0.000 (2)
N2	0.037 (3)	0.033 (3)	0.040 (3)	0.001 (2)	0.000 (2)	0.003 (2)
C1	0.028 (3)	0.040 (4)	0.036 (3)	0.002 (3)	−0.004 (3)	0.000 (3)
C2	0.029 (3)	0.038 (4)	0.039 (3)	−0.002 (3)	0.004 (3)	0.001 (3)
C3	0.029 (3)	0.039 (4)	0.037 (3)	0.001 (3)	0.005 (3)	−0.003 (3)
C4	0.024 (3)	0.039 (4)	0.031 (3)	−0.005 (3)	−0.001 (2)	0.000 (3)
C5	0.033 (3)	0.041 (4)	0.035 (3)	−0.004 (3)	−0.003 (3)	−0.003 (3)
C6	0.037 (3)	0.043 (4)	0.029 (3)	−0.003 (3)	−0.004 (3)	−0.002 (3)
C7	0.028 (3)	0.036 (4)	0.035 (3)	0.001 (3)	0.001 (2)	0.000 (3)
C8	0.033 (3)	0.027 (3)	0.038 (3)	−0.003 (3)	0.000 (3)	−0.002 (3)
C9	0.024 (3)	0.041 (4)	0.029 (3)	−0.002 (3)	0.000 (2)	−0.003 (3)
C10	0.037 (3)	0.041 (4)	0.038 (3)	0.006 (3)	−0.004 (3)	0.004 (3)
C11	0.049 (4)	0.060 (5)	0.037 (3)	−0.001 (3)	−0.001 (3)	0.004 (3)
C12	0.035 (3)	0.033 (4)	0.041 (3)	0.001 (3)	−0.004 (3)	−0.002 (3)
C13	0.035 (3)	0.044 (4)	0.048 (4)	−0.005 (3)	0.000 (3)	−0.002 (3)
C14	0.024 (3)	0.046 (4)	0.043 (4)	−0.002 (3)	−0.003 (3)	−0.004 (3)
C15	0.041 (4)	0.043 (4)	0.038 (3)	0.001 (3)	0.002 (3)	−0.001 (3)
C16	0.037 (3)	0.035 (4)	0.038 (3)	−0.004 (3)	0.000 (3)	−0.002 (3)
C17	0.032 (3)	0.039 (4)	0.045 (3)	0.003 (3)	−0.001 (3)	0.005 (3)
C18	0.040 (4)	0.041 (4)	0.033 (3)	−0.004 (3)	−0.007 (3)	−0.002 (3)
Cl1	0.0594 (11)	0.0574 (12)	0.0846 (14)	0.0021 (9)	−0.0195 (10)	0.0164 (10)
Cl2	0.0533 (11)	0.0680 (14)	0.0826 (14)	−0.0007 (10)	−0.0107 (10)	−0.0173 (10)
Cl3	0.0478 (10)	0.0679 (13)	0.0587 (11)	0.0016 (9)	0.0030 (8)	0.0095 (9)
C1S	0.033 (3)	0.058 (5)	0.056 (4)	−0.001 (3)	−0.001 (3)	0.003 (3)

Geometric parameters (Å, º)

O1—C9	1.380 (6)	C8—C9	1.373 (8)
O1—C1	1.393 (7)	C8—H8A	0.9500
O2—C1	1.201 (6)	C10—C11	1.511 (8)
O3—C14	1.212 (7)	C10—H10A	0.9900
O4—N2	1.390 (6)	C10—H10B	0.9900
O4—C14	1.393 (7)	C11—H11A	0.9800
O5—C15	1.203 (7)	C11—H11B	0.9800
O6—C18	1.215 (7)	C11—H11C	0.9800
N1—C7	1.359 (7)	C12—C13	1.530 (8)
N1—C12	1.471 (7)	C12—H12A	0.9900
N1—C10	1.478 (7)	C12—H12B	0.9900
N2—C18	1.383 (8)	C13—H13A	0.9800
N2—C15	1.400 (8)	C13—H13B	0.9800
C1—C2	1.452 (8)	C13—H13C	0.9800
C2—C3	1.368 (8)	C15—C16	1.497 (8)
C2—C14	1.468 (8)	C16—C17	1.533 (8)
C3—C4	1.405 (8)	C16—H16A	0.9900
C3—H3A	0.9500	C16—H16B	0.9900
C4—C9	1.401 (8)	C17—C18	1.498 (8)
C4—C5	1.401 (8)	C17—H17A	0.9900
C5—C6	1.364 (8)	C17—H17B	0.9900
C5—H5A	0.9500	Cl1—C1S	1.760 (7)
C6—C7	1.423 (8)	Cl2—C1S	1.752 (7)
C6—H6A	0.9500	Cl3—C1S	1.775 (7)
C7—C8	1.421 (8)	C1S—H1SA	1.0000
C9—O1—C1	123.6 (4)	H11A—C11—H11B	109.5
N2—O4—C14	111.2 (4)	C10—C11—H11C	109.5
C7—N1—C12	121.4 (5)	H11A—C11—H11C	109.5
C7—N1—C10	122.3 (5)	H11B—C11—H11C	109.5
C12—N1—C10	116.2 (5)	N1—C12—C13	112.7 (5)
C18—N2—O4	122.2 (5)	N1—C12—H12A	109.1
C18—N2—C15	115.2 (5)	C13—C12—H12A	109.1
O4—N2—C15	121.4 (5)	N1—C12—H12B	109.1
O2—C1—O1	115.7 (5)	C13—C12—H12B	109.1
O2—C1—C2	128.3 (6)	H12A—C12—H12B	107.8
O1—C1—C2	116.0 (5)	C12—C13—H13A	109.5
C3—C2—C1	120.2 (5)	C12—C13—H13B	109.5
C3—C2—C14	115.8 (5)	H13A—C13—H13B	109.5
C1—C2—C14	124.0 (5)	C12—C13—H13C	109.5
C2—C3—C4	121.9 (5)	H13A—C13—H13C	109.5
C2—C3—H3A	119.1	H13B—C13—H13C	109.5
C4—C3—H3A	119.1	O3—C14—O4	120.8 (6)
C9—C4—C5	117.3 (5)	O3—C14—C2	125.9 (5)
C9—C4—C3	118.5 (5)	O4—C14—C2	113.3 (5)
C5—C4—C3	124.0 (6)	O5—C15—N2	124.4 (6)
C6—C5—C4	121.6 (6)	O5—C15—C16	129.9 (6)
C6—C5—H5A	119.2	N2—C15—C16	105.7 (5)
C4—C5—H5A	119.2	C15—C16—C17	106.2 (5)
C5—C6—C7	120.6 (5)	C15—C16—H16A	110.5
C5—C6—H6A	119.7	C17—C16—H16A	110.5
C7—C6—H6A	119.7	C15—C16—H16B	110.5
N1—C7—C8	121.8 (5)	C17—C16—H16B	110.5
N1—C7—C6	119.7 (5)	H16A—C16—H16B	108.7
C8—C7—C6	118.5 (5)	C18—C17—C16	105.5 (5)
C9—C8—C7	118.7 (5)	C18—C17—H17A	110.6
C9—C8—H8A	120.6	C16—C17—H17A	110.6
C7—C8—H8A	120.6	C18—C17—H17B	110.6
C8—C9—O1	117.2 (5)	C16—C17—H17B	110.6
C8—C9—C4	123.2 (5)	H17A—C17—H17B	108.8
O1—C9—C4	119.5 (5)	O6—C18—N2	123.9 (6)
N1—C10—C11	112.9 (5)	O6—C18—C17	129.7 (6)
N1—C10—H10A	109.0	N2—C18—C17	106.5 (5)
C11—C10—H10A	109.0	Cl2—C1S—Cl1	110.6 (4)
N1—C10—H10B	109.0	Cl2—C1S—Cl3	109.6 (4)
C11—C10—H10B	109.0	Cl1—C1S—Cl3	108.5 (4)
H10A—C10—H10B	107.8	Cl2—C1S—H1SA	109.4
C10—C11—H11A	109.5	Cl1—C1S—H1SA	109.4
C10—C11—H11B	109.5	Cl3—C1S—H1SA	109.4

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
C1S—H1SA···O6^i	1.00	2.28	3.240 (7)	160
C3—H3A···O3^ii	0.95	2.59	3.219 (7)	124
C5—H5A···O6^ii	0.95	2.50	3.395 (7)	157
C11—H11C···O6^iii	0.98	2.53	3.473 (9)	162
C12—H12B···O3^iv	0.99	2.54	3.358 (8)	140
C16—H16B···O4^v	0.99	2.42	3.195 (8)	135

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