Diethyl 2-[(morpholin-4-yl)(phen­yl)meth­yl]malonate

In the title compound, C₁₈H₂₅NO₅, the morpholine unit adopts an almost ideal chair conformation. The crystal structure is consolidated by C—H...O inter­molecular hydrogen-bond inter­actions, providing stabilization. The mol­ecular conformation shows two possible pockets ready to coordinate two metal atoms.

Key indicators

• Single-crystal X-ray study
• T = 296 K
• Mean [sigma](C-C) = 0.004 Å
• R factor = 0.041
• wR factor = 0.112
• Data-to-parameter ratio = 10.1

checkCIF/PLATON results

No syntax errors found



Alert level A
PLAT222_ALERT_3_A Large Non-Solvent    H     Ueq(max)/Ueq(min) ...       5.45 Ratio

Alert level B
PLAT220_ALERT_2_B Large Non-Solvent    C     Ueq(max)/Ueq(min) ...       4.35 Ratio
PLAT242_ALERT_2_B Check Low       Ueq as Compared to Neighbors for        C17

Alert level C
PLAT063_ALERT_3_C Crystal Probably too Large for Beam Size .......       0.66 mm
PLAT066_ALERT_1_C Predicted and Reported Transmissions Identical .          ?
PLAT360_ALERT_2_C Short  C(sp3)-C(sp3) Bond  C17    -   C18    ...       1.35 Ang.

Alert level G
REFLT03_ALERT_4_G Please check that the estimate of the number of Friedel pairs is
            correct. If it is not, please give the correct count in the
            _publ_section_exptl_refinement section of the submitted CIF.
           From the CIF: _diffrn_reflns_theta_max           27.90
           From the CIF: _reflns_number_total               2217
           Count of symmetry unique reflns         2253
           Completeness (_total/calc)             98.40%
           TEST3: Check Friedels for noncentro structure
           Estimate of Friedel pairs measured         0
           Fraction of Friedel pairs measured     0.000
           Are heavy atom types Z>Si present         no
PLAT792_ALERT_1_G Check the Absolute Configuration of C7     = ...          R

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

   2 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
   3 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


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.

Author Response: Each author has made a unique and important contribution to this study. We ask that each author be listed as given.

   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

---

Computing details

Data collection: X-AREA (Stoe & Cie, 2002); cell refinement: X-AREA; data reduction: X-RED32 (Stoe & Cie, 2002); program(s) used to solve structure: SIR97 (Altomare et al., 1999); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997); software used to prepare material for publication: WinGX (Farrugia, 1999).

Diethyl 2-[morpholin-4-yl(phenyl)methyl]malonate

Crystal data

C18H25NO5	^1HNMR (CDCl3, δ p.p.m., J Hz): 1.01 (s, 3H), 1.51 (t, 3H), 1.9–2.0 (m, 4H, CH2N), 3.50–4.5 (m, 10H), 7.20 (m, 5H). MS m/z calculated for C18H25NO5: [MH] = 336 g /mol, found: 176 (100%), 159, 152, 150, 142, 131, 107, 105.
Mr = 335.39	Dx = 1.226 Mg m^−3
Orthorhombic, Pca21	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2c -2ac	Cell parameters from 12179 reflections
a = 9.1421 (6) Å	θ = 1.8–27.9°
b = 11.5978 (7) Å	µ = 0.09 mm^−1
c = 17.1379 (15) Å	T = 296 K
V = 1817.1 (2) Å^3	Prism, colourless
Z = 4	0.66 × 0.55 × 0.46 mm
F(000) = 720

Data collection

Sroe IPDS-II diffractometer	2217 independent reflections
Radiation source: sealed X-ray tube, 12 x 0.4 mm long-fine focus	1725 reflections with I > 2σ(I)
Plane graphite monochromator	Rint = 0.057
Detector resolution: 6.67 pixels mm^-1	θmax = 27.9°, θmin = 2.4°
ω scans	h = −11→11
Absorption correction: integration (X-RED32; Stoe & Cie, 2002)	k = −15→15
Tmin = 0.943, Tmax = 0.960	l = −22→22
11536 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)] = 0.041	H-atom parameters constrained
wR(F^2) = 0.112	w = 1/[σ^2(Fo^2) + (0.0742P)^2] where P = (Fo^2 + 2Fc^2)/3
S = 1.00	(Δ/σ)max < 0.001
2217 reflections	Δρmax = 0.15 e Å^−3
220 parameters	Δρmin = −0.14 e Å^−3
1 restraint	Extinction correction: SHELXL97, Fc^*=kFc[1+0.001xFc^2λ^3/sin(2θ)]^-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.014 (3)

Special details

Geometry. Bond distances, angles etc. have been calculated using the rounded fractional coordinates. All su's are estimated from the variances of the (full) variance-covariance matrix. The cell e.s.d.'s are taken into account in the estimation of distances, angles and torsion angles

Refinement. Refinement on F² for ALL reflections except those flagged by the user for potential systematic errors. Weighted R-factors wR and all goodnesses of fit S are based on F², conventional R-factors R are based on F, with F set to zero for negative F². The observed criterion of F² > σ(F²) is used only for calculating -R-factor-obs 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	0.3201 (3)	0.4017 (2)	0.86043 (18)	0.0970 (10)
O2	−0.2320 (2)	0.04845 (14)	0.69751 (15)	0.0704 (7)
O3	−0.35927 (17)	0.20271 (15)	0.66132 (12)	0.0574 (5)
O4	0.0207 (2)	0.18778 (19)	0.59299 (12)	0.0703 (7)
O5	−0.0268 (3)	0.37208 (18)	0.61808 (14)	0.0790 (7)
N1	0.1050 (2)	0.26946 (16)	0.78071 (12)	0.0506 (6)
C1	−0.0943 (2)	0.1489 (2)	0.84190 (14)	0.0480 (6)
C2	−0.0524 (3)	0.0484 (2)	0.87891 (16)	0.0562 (7)
C3	−0.1225 (3)	0.0113 (3)	0.94583 (16)	0.0674 (9)
C4	−0.2350 (3)	0.0755 (3)	0.97755 (17)	0.0683 (9)
C5	−0.2765 (3)	0.1749 (3)	0.94189 (18)	0.0716 (10)
C6	−0.2079 (3)	0.2119 (2)	0.87456 (16)	0.0604 (8)
C7	−0.0150 (2)	0.18708 (18)	0.76833 (13)	0.0444 (6)
C8	0.0660 (3)	0.3738 (2)	0.8233 (2)	0.0718 (10)
C9	0.1961 (4)	0.4530 (3)	0.8252 (3)	0.0917 (13)
C10	0.3570 (4)	0.2994 (4)	0.8201 (3)	0.0921 (15)
C11	0.2315 (3)	0.2157 (3)	0.8186 (2)	0.0672 (9)
C12	−0.1209 (2)	0.23591 (19)	0.70670 (14)	0.0462 (6)
C13	−0.2409 (2)	0.15011 (18)	0.68853 (14)	0.0466 (6)
C14	−0.4849 (2)	0.1285 (2)	0.64470 (19)	0.0642 (9)
C15	−0.5899 (4)	0.1966 (3)	0.5970 (3)	0.0910 (13)
C16	−0.0339 (3)	0.2606 (2)	0.63254 (15)	0.0533 (7)
C17	0.0616 (6)	0.4049 (4)	0.5505 (3)	0.1050 (17)
C18	0.1087 (10)	0.5149 (5)	0.5565 (5)	0.193 (4)
H2	0.02420	0.00500	0.85850	0.0670*
H3	−0.09380	−0.05720	0.96960	0.0810*
H4	−0.28190	0.05100	1.02280	0.0820*
H5	−0.35210	0.21860	0.96310	0.0860*
H6	−0.23820	0.28000	0.85080	0.0720*
H7	0.02880	0.11770	0.74560	0.0530*
H8A	0.03680	0.35430	0.87610	0.0860*
H8B	−0.01560	0.41180	0.79790	0.0860*
H9A	0.22060	0.47530	0.77220	0.1100*
H9B	0.17050	0.52230	0.85370	0.1100*
H10A	0.44030	0.26350	0.84530	0.1100*
H10B	0.38480	0.31830	0.76710	0.1100*
H11A	0.25960	0.14680	0.79030	0.0810*
H11B	0.20600	0.19360	0.87150	0.0810*
H12	−0.16430	0.30770	0.72610	0.0550*
H14A	−0.53080	0.10410	0.69300	0.0770*
H14B	−0.45370	0.06050	0.61630	0.0770*
H15A	−0.61230	0.26750	0.62330	0.1360*
H15B	−0.67810	0.15300	0.58970	0.1360*
H15C	−0.54710	0.21330	0.54710	0.1360*
H17A	0.14520	0.35370	0.54650	0.1260*
H17B	0.00380	0.39650	0.50330	0.1260*
H18A	0.14310	0.52860	0.60860	0.2890*
H18B	0.02940	0.56650	0.54510	0.2890*
H18C	0.18690	0.52760	0.52020	0.2890*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
O1	0.0872 (16)	0.1027 (18)	0.1010 (17)	−0.0352 (14)	−0.0251 (14)	−0.0124 (14)
O2	0.0600 (10)	0.0477 (9)	0.1035 (16)	−0.0010 (7)	−0.0223 (11)	−0.0001 (10)
O3	0.0397 (7)	0.0517 (8)	0.0809 (11)	−0.0018 (6)	−0.0097 (7)	0.0055 (8)
O4	0.0662 (11)	0.0865 (13)	0.0583 (10)	0.0015 (10)	0.0069 (9)	−0.0052 (10)
O5	0.0938 (14)	0.0674 (12)	0.0759 (12)	−0.0133 (11)	0.0121 (12)	0.0156 (10)
N1	0.0430 (9)	0.0527 (10)	0.0562 (11)	−0.0056 (8)	−0.0033 (8)	−0.0036 (9)
C1	0.0453 (10)	0.0485 (11)	0.0502 (11)	−0.0028 (9)	−0.0037 (9)	−0.0037 (10)
C2	0.0553 (12)	0.0543 (13)	0.0589 (13)	0.0030 (11)	−0.0069 (10)	0.0041 (11)
C3	0.0730 (16)	0.0688 (16)	0.0604 (15)	−0.0098 (13)	−0.0076 (13)	0.0156 (14)
C4	0.0643 (15)	0.0883 (18)	0.0524 (13)	−0.0214 (14)	0.0014 (13)	0.0071 (14)
C5	0.0592 (15)	0.091 (2)	0.0645 (16)	0.0002 (14)	0.0147 (13)	0.0004 (15)
C6	0.0578 (14)	0.0596 (14)	0.0638 (15)	0.0085 (10)	0.0094 (11)	0.0044 (12)
C7	0.0411 (10)	0.0430 (10)	0.0492 (11)	0.0014 (8)	−0.0022 (8)	−0.0029 (9)
C8	0.0642 (15)	0.0542 (15)	0.097 (2)	−0.0048 (12)	−0.0041 (15)	−0.0167 (14)
C9	0.099 (2)	0.0662 (18)	0.110 (3)	−0.0290 (18)	−0.010 (2)	−0.0126 (18)
C10	0.0542 (15)	0.119 (3)	0.103 (3)	−0.0174 (16)	−0.0171 (17)	−0.012 (2)
C11	0.0484 (13)	0.0751 (16)	0.0782 (18)	−0.0005 (12)	−0.0129 (12)	−0.0058 (15)
C12	0.0420 (10)	0.0467 (10)	0.0500 (11)	0.0002 (8)	−0.0020 (8)	−0.0012 (9)
C13	0.0421 (10)	0.0471 (10)	0.0506 (11)	0.0024 (8)	−0.0004 (9)	0.0021 (10)
C14	0.0397 (10)	0.0649 (15)	0.0880 (19)	−0.0077 (10)	−0.0040 (12)	−0.0034 (14)
C15	0.0569 (16)	0.090 (2)	0.126 (3)	0.0061 (15)	−0.0317 (19)	−0.005 (2)
C16	0.0466 (11)	0.0620 (14)	0.0514 (12)	−0.0073 (10)	−0.0074 (10)	0.0045 (11)
C17	0.121 (3)	0.104 (3)	0.090 (3)	−0.034 (3)	0.023 (2)	0.025 (2)
C18	0.268 (10)	0.121 (4)	0.190 (7)	−0.087 (5)	0.122 (7)	−0.014 (4)

Geometric parameters (Å, º)

O1—C9	1.416 (5)	C2—H2	0.9300
O1—C10	1.414 (5)	C3—H3	0.9300
O2—C13	1.192 (3)	C4—H4	0.9300
O3—C13	1.327 (3)	C5—H5	0.9300
O3—C14	1.463 (3)	C6—H6	0.9300
O4—C16	1.192 (3)	C7—H7	0.9800
O5—C16	1.318 (3)	C8—H8A	0.9700
O5—C17	1.463 (6)	C8—H8B	0.9700
N1—C7	1.470 (3)	C9—H9A	0.9700
N1—C8	1.458 (3)	C9—H9B	0.9700
N1—C11	1.466 (4)	C10—H10A	0.9700
C1—C2	1.381 (3)	C10—H10B	0.9700
C1—C6	1.388 (3)	C11—H11A	0.9700
C1—C7	1.520 (3)	C11—H11B	0.9700
C2—C3	1.382 (4)	C12—H12	0.9800
C3—C4	1.381 (4)	C14—H14A	0.9700
C4—C5	1.359 (5)	C14—H14B	0.9700
C5—C6	1.382 (4)	C15—H15A	0.9600
C7—C12	1.541 (3)	C15—H15B	0.9600
C8—C9	1.503 (4)	C15—H15C	0.9600
C10—C11	1.503 (5)	C17—H17A	0.9700
C12—C13	1.514 (3)	C17—H17B	0.9700
C12—C16	1.526 (3)	C18—H18A	0.9600
C14—C15	1.488 (5)	C18—H18B	0.9600
C17—C18	1.350 (8)	C18—H18C	0.9600
O1···N1	2.844 (3)	H4···C13^vii	3.0700
O2···C1	3.011 (3)	H5···O4^vii	2.7300
O2···C14^i	3.183 (3)	H5···H17B^vii	2.5800
O5···N1	3.261 (3)	H6···C8	3.0200
O1···H8B^ii	2.8400	H6···C12	2.7400
O2···H14A	2.8100	H6···H12	2.2600
O2···H14B	2.4600	H6···H9B^viii	2.4400
O2···H11A^iii	2.7700	H7···O2	2.6500
O2···H14A^i	2.5500	H7···O4	2.7400
O2···H7	2.6500	H7···H2	2.3400
O4···H15B^iv	2.7800	H7···H11A	2.2700
O4···H17A	2.3700	H8A···C1	2.7300
O4···H17B	2.8700	H8A···C6	2.7800
O4···H3^v	2.6900	H8A···H11B	2.4200
O4···H5^vi	2.7300	H8B···C12	2.7400
O4···H14B^i	2.9200	H8B···H12	2.2000
O4···H7	2.7400	H8B···O1^viii	2.8400
N1···O1	2.844 (3)	H9A···H10B	2.3600
N1···O5	3.261 (3)	H9B···H6^ii	2.4400
C1···O2	3.011 (3)	H10B···H9A	2.3600
C2···C11	3.401 (4)	H10B···H15A^iv	2.5300
C4···C14^vii	3.553 (4)	H11A···H7	2.2700
C6···C8	3.251 (4)	H11A···H14A^iv	2.5900
C6···C13	3.282 (4)	H11A···O2^i	2.7700
C8···C6	3.251 (4)	H11B···C1	2.8400
C11···C2	3.401 (4)	H11B···C2	2.9000
C13···C6	3.282 (4)	H11B···H8A	2.4200
C14···O2^iii	3.183 (3)	H12···C6	2.8000
C14···C4^vi	3.553 (4)	H12···C8	2.7900
C1···H11B	2.8400	H12···H6	2.2600
C1···H8A	2.7300	H12···H8B	2.2000
C2···H11B	2.9000	H14A···O2	2.8100
C3···H14B^vii	3.0600	H14A···H11A^x	2.5900
C4···H14B^vii	2.9400	H14A···O2^iii	2.5500
C6···H8A	2.7800	H14B···O2	2.4600
C6···H12	2.8000	H14B···C3^vi	3.0600
C8···H6	3.0200	H14B···C4^vi	2.9400
C8···H12	2.7900	H14B···O4^iii	2.9200
C12···H6	2.7400	H15A···H10B^x	2.5300
C12···H8B	2.7400	H15B···O4^x	2.7800
C13···H4^vi	3.0700	H17A···O4	2.3700
C15···H18B^viii	3.0900	H17B···O4	2.8700
H2···H7	2.3400	H17B···H5^vi	2.5800
H3···O4^ix	2.6900	H18B···C15^ii	3.0900
C9—O1—C10	109.6 (3)	N1—C8—H8A	110.00
C13—O3—C14	115.99 (18)	N1—C8—H8B	110.00
C16—O5—C17	115.6 (3)	C9—C8—H8A	110.00
C7—N1—C8	115.42 (18)	C9—C8—H8B	110.00
C7—N1—C11	112.11 (19)	H8A—C8—H8B	108.00
C8—N1—C11	108.9 (2)	O1—C9—H9A	109.00
C2—C1—C6	117.8 (2)	O1—C9—H9B	109.00
C2—C1—C7	119.6 (2)	C8—C9—H9A	109.00
C6—C1—C7	122.6 (2)	C8—C9—H9B	109.00
C1—C2—C3	121.0 (2)	H9A—C9—H9B	108.00
C2—C3—C4	120.3 (3)	O1—C10—H10A	109.00
C3—C4—C5	119.2 (3)	O1—C10—H10B	109.00
C4—C5—C6	120.8 (3)	C11—C10—H10A	109.00
C1—C6—C5	120.9 (2)	C11—C10—H10B	109.00
N1—C7—C1	115.18 (18)	H10A—C10—H10B	108.00
N1—C7—C12	109.21 (17)	N1—C11—H11A	110.00
C1—C7—C12	112.08 (16)	N1—C11—H11B	110.00
N1—C8—C9	108.9 (2)	C10—C11—H11A	110.00
O1—C9—C8	112.7 (3)	C10—C11—H11B	110.00
O1—C10—C11	111.6 (3)	H11A—C11—H11B	108.00
N1—C11—C10	109.6 (3)	C7—C12—H12	110.00
C7—C12—C13	110.79 (18)	C13—C12—H12	110.00
C7—C12—C16	108.20 (17)	C16—C12—H12	110.00
C13—C12—C16	109.25 (19)	O3—C14—H14A	110.00
O2—C13—O3	123.8 (2)	O3—C14—H14B	110.00
O2—C13—C12	125.06 (19)	C15—C14—H14A	110.00
O3—C13—C12	111.17 (18)	C15—C14—H14B	110.00
O3—C14—C15	107.5 (2)	H14A—C14—H14B	109.00
O4—C16—O5	124.6 (3)	C14—C15—H15A	110.00
O4—C16—C12	124.0 (2)	C14—C15—H15B	110.00
O5—C16—C12	111.5 (2)	C14—C15—H15C	109.00
O5—C17—C18	111.2 (5)	H15A—C15—H15B	109.00
C1—C2—H2	120.00	H15A—C15—H15C	109.00
C3—C2—H2	119.00	H15B—C15—H15C	109.00
C2—C3—H3	120.00	O5—C17—H17A	109.00
C4—C3—H3	120.00	O5—C17—H17B	109.00
C3—C4—H4	120.00	C18—C17—H17A	109.00
C5—C4—H4	120.00	C18—C17—H17B	109.00
C4—C5—H5	120.00	H17A—C17—H17B	108.00
C6—C5—H5	120.00	C17—C18—H18A	109.00
C1—C6—H6	120.00	C17—C18—H18B	109.00
C5—C6—H6	120.00	C17—C18—H18C	109.00
N1—C7—H7	107.00	H18A—C18—H18B	109.00
C1—C7—H7	107.00	H18A—C18—H18C	109.00
C12—C7—H7	107.00	H18B—C18—H18C	110.00
C10—O1—C9—C8	57.7 (5)	C6—C1—C2—C3	0.7 (4)
C9—O1—C10—C11	−57.5 (4)	C2—C1—C7—C12	139.6 (2)
C13—O3—C14—C15	−165.9 (3)	C6—C1—C7—C12	−41.0 (3)
C14—O3—C13—C12	−177.6 (2)	C1—C2—C3—C4	−0.9 (4)
C14—O3—C13—O2	2.1 (4)	C2—C3—C4—C5	0.5 (4)
C17—O5—C16—C12	176.6 (3)	C3—C4—C5—C6	0.2 (5)
C16—O5—C17—C18	−156.6 (5)	C4—C5—C6—C1	−0.4 (4)
C17—O5—C16—O4	−3.3 (5)	N1—C7—C12—C13	176.38 (17)
C7—N1—C11—C10	172.6 (3)	C1—C7—C12—C16	−174.50 (18)
C8—N1—C7—C12	72.5 (3)	N1—C7—C12—C16	56.6 (2)
C11—N1—C7—C12	−162.0 (2)	C1—C7—C12—C13	−54.8 (2)
C7—N1—C8—C9	−175.3 (3)	N1—C8—C9—O1	−58.4 (4)
C8—N1—C7—C1	−54.7 (3)	O1—C10—C11—N1	58.9 (4)
C11—N1—C7—C1	70.8 (2)	C7—C12—C13—O2	−24.1 (3)
C11—N1—C8—C9	57.6 (3)	C13—C12—C16—O5	126.4 (2)
C8—N1—C11—C10	−58.4 (3)	C7—C12—C13—O3	155.65 (19)
C7—C1—C2—C3	−179.9 (2)	C16—C12—C13—O2	95.1 (3)
C2—C1—C6—C5	0.0 (4)	C16—C12—C13—O3	−85.2 (2)
C2—C1—C7—N1	−94.7 (3)	C7—C12—C16—O4	67.0 (3)
C6—C1—C7—N1	84.7 (3)	C7—C12—C16—O5	−112.9 (2)
C7—C1—C6—C5	−179.4 (2)	C13—C12—C16—O4	−53.7 (3)

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

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
C14—H14A···O2^iii	0.97	2.55	3.183 (3)	123

Symmetry code: (iii) x−1/2, −y, z.