Ethyl 2-{[2-(2-eth­oxy-2-oxoeth­oxy)quinolin-4-yl]carbon­yloxy}acetate

The conformation of the 2-eth­oxy-2-oxoeth­oxy side chain, including a gauche C_e—O—C—C₃ [72.46 (16)°] (e = eth­oxy) unit, in the title compound, C₁₈H₁₉NO₇, is partly determined by an intra­molecular C—H...O hydrogen bond. In the crystal, C—H...O hydrogen bonds and C—H...π inter­actions arising from the same methyl­ene group form chains extending along the a-axis direction.

Key indicators

• Single-crystal X-ray study
• T = 150 K
• Mean [sigma](C-C) = 0.002 Å
• R factor = 0.037
• wR factor = 0.099
• Data-to-parameter ratio = 10.6

checkCIF/PLATON results

No syntax errors found



Alert level C
PLAT029_ALERT_3_C _diffrn_measured_fraction_theta_full value Low .      0.963 Why?
PLAT481_ALERT_4_C Long D...A H-Bond Reported C10      ..CG2              4.02 Ang.
PLAT911_ALERT_3_C Missing FCF Refl Between Thmin & STh/L=    0.600        111 Report

Alert level G
PLAT066_ALERT_1_G Predicted and Reported Tmin&Tmax Range Identical          ? Check
PLAT154_ALERT_1_G The s.u.'s on the Cell Angles are Equal ..(Note)      0.002 Degree
PLAT910_ALERT_3_G Missing # of FCF Reflection(s) Below Theta(Min).          1 Note
PLAT912_ALERT_4_G Missing # of FCF Reflections Above STh/L=  0.600        152 Note
PLAT978_ALERT_2_G Number C-C Bonds with Positive Residual Density.         13 Info

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

   2 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
   3 ALERT type 3 Indicator that the structure quality may be low
   2 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: APEX3 (Bruker, 2016); cell refinement: SAINT (Bruker, 2016); data reduction: SAINT (Bruker, 2016); program(s) used to solve structure: SHELXT (Sheldrick, 2015a); program(s) used to refine structure: SHELXL2018/1 (Sheldrick, 2015b); molecular graphics: DIAMOND (Brandenburg & Putz, 2012); software used to prepare material for publication: SHELXTL (Sheldrick, 2008).

Ethyl 2-{[2-(2-ethoxy-2-oxoethoxy)quinolin-4-yl]carbonyloxy}acetate

Crystal data

C18H19NO7	Z = 2
Mr = 361.34	F(000) = 380
Triclinic, P1	Dx = 1.381 Mg m^−3
a = 4.9417 (2) Å	Cu Kα radiation, λ = 1.54178 Å
b = 7.6157 (3) Å	Cell parameters from 5397 reflections
c = 23.4472 (9) Å	θ = 3.8–74.5°
α = 94.490 (2)°	µ = 0.91 mm^−1
β = 92.997 (2)°	T = 150 K
γ = 98.136 (2)°	Block, colourless
V = 869.06 (6) Å^3	0.19 × 0.14 × 0.08 mm

Data collection

Bruker D8 VENTURE PHOTON 100 CMOS diffractometer	3301 independent reflections
Radiation source: INCOATEC IµS micro–focus source	2894 reflections with I > 2σ(I)
Mirror monochromator	Rint = 0.023
Detector resolution: 10.4167 pixels mm^-1	θmax = 74.5°, θmin = 3.8°
ω scans	h = −5→6
Absorption correction: multi-scan (SADABS; Krause et al., 2015)	k = −9→9
Tmin = 0.85, Tmax = 0.93	l = −27→29
6827 measured reflections

Refinement

Refinement on F^2	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: difference Fourier map
R[F^2 > 2σ(F^2)] = 0.037	All H-atom parameters refined
wR(F^2) = 0.099	w = 1/[σ^2(Fo^2) + (0.0479P)^2 + 0.2771P] where P = (Fo^2 + 2Fc^2)/3
S = 1.03	(Δ/σ)max < 0.001
3301 reflections	Δρmax = 0.29 e Å^−3
312 parameters	Δρmin = −0.19 e Å^−3
0 restraints	Extinction correction: SHELXL-2018/1 (Sheldrick, 2015b), Fc^*=kFc[1+0.001xFc^2λ^3/sin(2θ)]^-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.0144 (10)

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. 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 > 2sigma(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	0.9795 (2)	0.19616 (13)	0.19654 (4)	0.0298 (2)
O2	0.6525 (2)	0.10059 (14)	0.09687 (4)	0.0347 (3)
O3	0.9762 (2)	0.24142 (13)	0.04573 (4)	0.0314 (2)
O4	0.3329 (3)	0.15037 (15)	0.35154 (5)	0.0549 (4)
O5	0.3071 (2)	0.43440 (13)	0.37905 (4)	0.0317 (2)
O6	0.5808 (2)	0.31430 (16)	0.46977 (5)	0.0409 (3)
O7	0.1851 (2)	0.22790 (15)	0.50923 (4)	0.0370 (3)
N1	0.7797 (2)	0.45027 (15)	0.19139 (5)	0.0264 (3)
C1	0.6133 (3)	0.56258 (17)	0.21529 (5)	0.0253 (3)
C2	0.5848 (3)	0.71671 (19)	0.18733 (6)	0.0322 (3)
H2	0.691 (4)	0.735 (2)	0.1526 (8)	0.041 (5)*
C3	0.4194 (3)	0.83331 (19)	0.20776 (6)	0.0348 (3)
H3	0.403 (4)	0.937 (3)	0.1890 (8)	0.043 (5)*
C4	0.2734 (3)	0.80006 (19)	0.25639 (6)	0.0341 (3)
H4	0.157 (4)	0.883 (3)	0.2708 (8)	0.046 (5)*
C5	0.2999 (3)	0.65216 (19)	0.28472 (6)	0.0304 (3)
H5	0.198 (4)	0.632 (2)	0.3188 (8)	0.042 (5)*
C6	0.4736 (3)	0.53005 (17)	0.26569 (5)	0.0250 (3)
C7	0.5175 (3)	0.37093 (17)	0.29200 (5)	0.0258 (3)
C8	0.6876 (3)	0.26321 (18)	0.26838 (6)	0.0266 (3)
H8	0.720 (3)	0.155 (2)	0.2853 (7)	0.035 (4)*
C9	0.8144 (3)	0.31020 (17)	0.21775 (5)	0.0246 (3)
C10	1.0894 (3)	0.2362 (2)	0.14312 (6)	0.0291 (3)
H10A	1.229 (4)	0.163 (2)	0.1374 (7)	0.040 (5)*
H10B	1.164 (3)	0.363 (2)	0.1426 (7)	0.032 (4)*
C11	0.8761 (3)	0.18459 (17)	0.09398 (6)	0.0257 (3)
C12	0.7954 (3)	0.1969 (2)	−0.00618 (6)	0.0393 (4)
H12A	0.743 (4)	0.062 (3)	−0.0114 (8)	0.052 (5)*
H12B	0.632 (4)	0.253 (3)	−0.0010 (8)	0.052 (5)*
C13	0.9522 (4)	0.2659 (3)	−0.05472 (7)	0.0476 (4)
H13A	1.130 (5)	0.207 (3)	−0.0576 (10)	0.072 (7)*
H13B	0.832 (5)	0.235 (3)	−0.0907 (10)	0.070 (7)*
H13C	1.009 (5)	0.394 (3)	−0.0492 (10)	0.066 (6)*
C14	0.3772 (3)	0.30534 (19)	0.34306 (6)	0.0309 (3)
C15	0.1559 (3)	0.3732 (2)	0.42636 (6)	0.0339 (3)
H15A	0.005 (4)	0.282 (3)	0.4126 (8)	0.042 (5)*
H15B	0.094 (4)	0.479 (3)	0.4439 (8)	0.043 (5)*
C16	0.3364 (3)	0.30131 (18)	0.46988 (6)	0.0273 (3)
C17	0.3261 (3)	0.1532 (2)	0.55576 (7)	0.0376 (4)
H17A	0.341 (4)	0.031 (3)	0.5435 (8)	0.052 (5)*
H17B	0.506 (4)	0.219 (3)	0.5618 (8)	0.047 (5)*
C18	0.1607 (4)	0.1651 (2)	0.60672 (7)	0.0403 (4)
H18A	0.249 (4)	0.113 (3)	0.6388 (9)	0.058 (6)*
H18B	−0.019 (4)	0.104 (3)	0.5980 (8)	0.050 (5)*
H18C	0.158 (5)	0.296 (3)	0.6203 (10)	0.069 (7)*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
O1	0.0316 (5)	0.0373 (5)	0.0231 (5)	0.0121 (4)	0.0057 (4)	0.0030 (4)
O2	0.0276 (5)	0.0424 (6)	0.0325 (5)	0.0004 (4)	0.0062 (4)	−0.0021 (4)
O3	0.0311 (5)	0.0395 (5)	0.0225 (5)	0.0015 (4)	0.0016 (4)	0.0026 (4)
O4	0.0931 (10)	0.0301 (6)	0.0388 (6)	−0.0094 (6)	0.0309 (6)	0.0011 (5)
O5	0.0359 (5)	0.0364 (5)	0.0256 (5)	0.0087 (4)	0.0141 (4)	0.0053 (4)
O6	0.0265 (5)	0.0575 (7)	0.0419 (6)	0.0097 (5)	0.0125 (4)	0.0108 (5)
O7	0.0269 (5)	0.0550 (7)	0.0322 (5)	0.0067 (4)	0.0076 (4)	0.0185 (5)
N1	0.0264 (5)	0.0309 (6)	0.0215 (5)	0.0026 (4)	0.0019 (4)	0.0021 (4)
C1	0.0249 (6)	0.0277 (6)	0.0218 (6)	0.0015 (5)	−0.0017 (5)	−0.0010 (5)
C2	0.0378 (8)	0.0332 (7)	0.0250 (7)	0.0013 (6)	0.0016 (6)	0.0061 (5)
C3	0.0440 (8)	0.0274 (7)	0.0322 (7)	0.0055 (6)	−0.0067 (6)	0.0039 (6)
C4	0.0369 (8)	0.0305 (7)	0.0339 (8)	0.0089 (6)	−0.0044 (6)	−0.0055 (6)
C5	0.0320 (7)	0.0331 (7)	0.0251 (7)	0.0032 (6)	0.0034 (6)	−0.0029 (5)
C6	0.0250 (6)	0.0261 (6)	0.0217 (6)	−0.0002 (5)	−0.0021 (5)	−0.0012 (5)
C7	0.0268 (6)	0.0278 (6)	0.0208 (6)	−0.0018 (5)	0.0019 (5)	−0.0007 (5)
C8	0.0310 (7)	0.0269 (6)	0.0213 (6)	0.0029 (5)	0.0011 (5)	0.0018 (5)
C9	0.0240 (6)	0.0292 (6)	0.0199 (6)	0.0033 (5)	−0.0001 (5)	−0.0004 (5)
C10	0.0245 (6)	0.0410 (8)	0.0230 (7)	0.0074 (6)	0.0057 (5)	0.0016 (5)
C11	0.0250 (6)	0.0275 (6)	0.0257 (7)	0.0079 (5)	0.0057 (5)	−0.0006 (5)
C12	0.0373 (8)	0.0537 (10)	0.0257 (7)	0.0070 (7)	−0.0040 (6)	−0.0009 (6)
C13	0.0662 (12)	0.0509 (10)	0.0253 (8)	0.0065 (9)	0.0009 (8)	0.0049 (7)
C14	0.0345 (7)	0.0309 (7)	0.0253 (7)	−0.0017 (6)	0.0064 (6)	−0.0013 (5)
C15	0.0299 (7)	0.0479 (9)	0.0264 (7)	0.0073 (6)	0.0128 (6)	0.0094 (6)
C16	0.0268 (7)	0.0290 (6)	0.0267 (7)	0.0046 (5)	0.0094 (5)	0.0001 (5)
C17	0.0367 (8)	0.0459 (9)	0.0349 (8)	0.0153 (7)	0.0064 (6)	0.0138 (7)
C18	0.0368 (8)	0.0522 (10)	0.0323 (8)	0.0047 (7)	0.0024 (7)	0.0097 (7)

Geometric parameters (Å, º)

O1—C9	1.3577 (15)	C6—C7	1.4401 (19)
O1—C10	1.4285 (16)	C7—C8	1.3633 (19)
O2—C11	1.2036 (17)	C7—C14	1.4988 (19)
O3—C11	1.3367 (16)	C8—C9	1.4180 (18)
O3—C12	1.4598 (17)	C8—H8	0.972 (18)
O4—C14	1.2035 (19)	C10—C11	1.5092 (19)
O5—C14	1.3399 (17)	C10—H10A	0.954 (19)
O5—C15	1.4405 (16)	C10—H10B	0.983 (17)
O6—C16	1.1978 (17)	C12—C13	1.498 (2)
O7—C16	1.3259 (17)	C12—H12A	1.02 (2)
O7—C17	1.4593 (18)	C12—H12B	0.97 (2)
N1—C9	1.3012 (17)	C13—H13A	1.05 (2)
N1—C1	1.3762 (17)	C13—H13B	1.00 (2)
C1—C2	1.4090 (19)	C13—H13C	0.97 (2)
C1—C6	1.4201 (19)	C15—C16	1.506 (2)
C2—C3	1.366 (2)	C15—H15A	0.96 (2)
C2—H2	1.001 (18)	C15—H15B	0.97 (2)
C3—C4	1.402 (2)	C17—C18	1.486 (2)
C3—H3	0.943 (19)	C17—H17A	0.97 (2)
C4—C5	1.370 (2)	C17—H17B	0.95 (2)
C4—H4	0.966 (19)	C18—H18A	0.99 (2)
C5—C6	1.4152 (19)	C18—H18B	0.95 (2)
C5—H5	0.978 (19)	C18—H18C	1.03 (3)
C9—O1—C10	115.23 (10)	O2—C11—C10	125.79 (12)
C11—O3—C12	116.03 (11)	O3—C11—C10	109.56 (11)
C14—O5—C15	115.02 (11)	O3—C12—C13	106.86 (13)
C16—O7—C17	117.59 (11)	O3—C12—H12A	108.1 (11)
C9—N1—C1	117.42 (11)	C13—C12—H12A	111.8 (11)
N1—C1—C2	116.81 (12)	O3—C12—H12B	108.2 (12)
N1—C1—C6	123.38 (12)	C13—C12—H12B	112.1 (12)
C2—C1—C6	119.81 (12)	H12A—C12—H12B	109.6 (16)
C3—C2—C1	120.40 (13)	C12—C13—H13A	109.5 (13)
C3—C2—H2	123.1 (10)	C12—C13—H13B	108.0 (13)
C1—C2—H2	116.5 (10)	H13A—C13—H13B	110.2 (18)
C2—C3—C4	120.43 (13)	C12—C13—H13C	112.1 (13)
C2—C3—H3	119.8 (11)	H13A—C13—H13C	107.2 (19)
C4—C3—H3	119.7 (11)	H13B—C13—H13C	109.8 (19)
C5—C4—C3	120.31 (13)	O4—C14—O5	122.56 (13)
C5—C4—H4	119.4 (11)	O4—C14—C7	123.18 (13)
C3—C4—H4	120.3 (11)	O5—C14—C7	114.25 (12)
C4—C5—C6	121.04 (13)	O5—C15—C16	111.47 (11)
C4—C5—H5	118.9 (11)	O5—C15—H15A	110.1 (11)
C6—C5—H5	120.0 (11)	C16—C15—H15A	109.7 (11)
C5—C6—C1	117.97 (12)	O5—C15—H15B	104.6 (11)
C5—C6—C7	125.85 (12)	C16—C15—H15B	108.7 (11)
C1—C6—C7	116.16 (12)	H15A—C15—H15B	112.2 (15)
C8—C7—C6	119.62 (12)	O6—C16—O7	125.43 (13)
C8—C7—C14	115.35 (12)	O6—C16—C15	124.80 (13)
C6—C7—C14	124.95 (12)	O7—C16—C15	109.73 (11)
C7—C8—C9	118.76 (12)	O7—C17—C18	107.62 (12)
C7—C8—H8	121.0 (10)	O7—C17—H17A	108.0 (12)
C9—C8—H8	120.2 (10)	C18—C17—H17A	111.4 (12)
N1—C9—O1	119.94 (11)	O7—C17—H17B	107.5 (12)
N1—C9—C8	124.63 (12)	C18—C17—H17B	113.4 (12)
O1—C9—C8	115.43 (11)	H17A—C17—H17B	108.7 (16)
O1—C10—C11	111.20 (11)	C17—C18—H18A	109.5 (12)
O1—C10—H10A	106.4 (11)	C17—C18—H18B	110.4 (12)
C11—C10—H10A	107.0 (11)	H18A—C18—H18B	109.9 (17)
O1—C10—H10B	112.6 (9)	C17—C18—H18C	109.8 (13)
C11—C10—H10B	109.0 (10)	H18A—C18—H18C	106.2 (18)
H10A—C10—H10B	110.5 (15)	H18B—C18—H18C	111.0 (17)
O2—C11—O3	124.61 (12)
C9—N1—C1—C2	177.99 (12)	C10—O1—C9—C8	175.21 (11)
C9—N1—C1—C6	−1.91 (18)	C7—C8—C9—N1	−0.3 (2)
N1—C1—C2—C3	178.82 (13)	C7—C8—C9—O1	−179.63 (11)
C6—C1—C2—C3	−1.3 (2)	C9—O1—C10—C11	−76.01 (14)
C1—C2—C3—C4	−0.8 (2)	C12—O3—C11—O2	0.38 (19)
C2—C3—C4—C5	1.5 (2)	C12—O3—C11—C10	178.34 (12)
C3—C4—C5—C6	−0.1 (2)	O1—C10—C11—O2	−8.81 (19)
C4—C5—C6—C1	−1.89 (19)	O1—C10—C11—O3	173.25 (10)
C4—C5—C6—C7	179.92 (12)	C11—O3—C12—C13	−177.61 (13)
N1—C1—C6—C5	−177.54 (12)	C15—O5—C14—O4	−4.6 (2)
C2—C1—C6—C5	2.56 (18)	C15—O5—C14—C7	176.06 (11)
N1—C1—C6—C7	0.83 (18)	C8—C7—C14—O4	−25.5 (2)
C2—C1—C6—C7	−179.08 (12)	C6—C7—C14—O4	151.15 (16)
C5—C6—C7—C8	178.79 (12)	C8—C7—C14—O5	153.84 (12)
C1—C6—C7—C8	0.57 (18)	C6—C7—C14—O5	−29.51 (19)
C5—C6—C7—C14	2.3 (2)	C14—O5—C15—C16	72.46 (16)
C1—C6—C7—C14	−175.94 (12)	C17—O7—C16—O6	−1.3 (2)
C6—C7—C8—C9	−0.84 (19)	C17—O7—C16—C15	−178.99 (13)
C14—C7—C8—C9	175.99 (11)	O5—C15—C16—O6	9.4 (2)
C1—N1—C9—O1	−179.05 (11)	O5—C15—C16—O7	−172.89 (12)
C1—N1—C9—C8	1.65 (19)	C16—O7—C17—C18	151.56 (14)
C10—O1—C9—N1	−4.16 (17)

Hydrogen-bond geometry (Å, º)

Cg2 is the centroid of the C1–C6 ring.

D—H···A	D—H	H···A	D···A	D—H···A
C5—H5···O5	0.977 (19)	2.244 (17)	2.8681 (17)	120.7 (14)
C10—H10A···O2^i	0.954 (19)	2.435 (19)	3.3079 (16)	152.1 (15)
C10—H10B···Cg2^i	0.983 (17)	3.249 (16)	4.0173 (14)	136.3 (15)

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