Methyl (2R)-2-benzamido-2-{[(1R)-2-meth­oxy-2-oxo-1-phenyl­eth­yl]amino}­acetate

In the title compound, C₁₉H₂₀N₂O₅, the dihedral angle between the phenyl rings is 58.85 (8)°, while that between the planes of the methyl acetate groups is 88.30 (8)°. The molecular conformation is also influenced by the presence of an intramolecular N—H...O hydrogen bond. In the crystal, N—H...O hydrogen bonds link the mol­ecules, forming chains propagating along the a-axis direction.

Key indicators

• Single-crystal X-ray study
• T = 173 K
• Mean [sigma](C-C) = 0.002 Å
• R factor = 0.027
• wR factor = 0.065
• Data-to-parameter ratio = 14.0

checkCIF/PLATON results

No syntax errors found



Alert level C
STRVA01_ALERT_4_C           Flack parameter is too small
           From the CIF: _refine_ls_abs_structure_Flack   -0.300
           From the CIF: _refine_ls_abs_structure_Flack_su    0.800
PLAT220_ALERT_2_C Non-Solvent Resd 1   C   Ueq(max)/Ueq(min) Range        3.1 Ratio
PLAT222_ALERT_3_C Non-Solvent Resd 1   H Uiso(max)/Uiso(min) Range        4.2 Ratio
PLAT911_ALERT_3_C Missing # FCF Refl Between THmin & STh/L=  0.600          2 Report

Alert level G
PLAT002_ALERT_2_G Number of Distance or Angle Restraints on AtSite          4 Note
PLAT032_ALERT_4_G Std. Uncertainty on Flack Parameter Value High .      0.800 Report
PLAT066_ALERT_1_G Predicted and Reported Tmin&Tmax Range Identical          ? Check
PLAT172_ALERT_4_G The CIF-Embedded .res File Contains DFIX Records          1 Report
PLAT791_ALERT_4_G The Model has Chirality at C14     (Chiral SPGR)          R Verify
PLAT791_ALERT_4_G The Model has Chirality at C15     (Chiral SPGR)          R Verify
PLAT860_ALERT_3_G Number of Least-Squares Restraints .............          2 Note
PLAT916_ALERT_2_G Hooft y and Flack x Parameter values differ by .       0.27 Check
PLAT933_ALERT_2_G Number of OMIT Records in Embedded .res File ...          2 Note
PLAT978_ALERT_2_G Number C-C Bonds with Positive Residual Density.          1 Note

   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
  10 ALERT level G = General information/check it is not something unexpected

   1 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
   5 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
   5 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

---

Computing details

Data collection: APEX2 (Bruker, 2005); cell refinement: SAINT (Bruker, 2005); data reduction: SAINT (Bruker, 2005); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL2014 (Sheldrick, 2015); molecular graphics: PLATON (Spek, 2009); software used to prepare material for publication: publCIF (Westrip, 2010).

Methyl (2R)-2-benzamido-2-{[(1R)-2-methoxy-2-oxo-1-phenylethyl]amino}acetate

Crystal data

C19H20N2O5	F(000) = 752
Mr = 356.37	Dx = 1.343 Mg m^−3
Orthorhombic, P212121	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2ac 2ab	Cell parameters from 365 reflections
a = 9.3432 (6) Å	θ = 1.6–25.2°
b = 10.4314 (8) Å	µ = 0.10 mm^−1
c = 18.0901 (14) Å	T = 173 K
V = 1763.1 (2) Å^3	Prism, colourless
Z = 4	0.35 × 0.16 × 0.14 mm

Data collection

Bruker APEXII CCD diffractometer	3455 independent reflections
Radiation source: fine-focus sealed tube	3246 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.029
φ and ω scan	θmax = 26.0°, θmin = 2.3°
Absorption correction: multi-scan (SADABS; Bruker, 2005)	h = −11→7
Tmin = 0.967, Tmax = 0.986	k = −12→12
28362 measured reflections	l = −22→22

Refinement

Refinement on F^2	Hydrogen site location: inferred from neighbouring sites
Least-squares matrix: full	H atoms treated by a mixture of independent and constrained refinement
R[F^2 > 2σ(F^2)] = 0.027	w = 1/[σ^2(Fo^2) + (0.0234P)^2 + 0.3377P] where P = (Fo^2 + 2Fc^2)/3
wR(F^2) = 0.065	(Δ/σ)max = 0.001
S = 1.04	Δρmax = 0.14 e Å^−3
3455 reflections	Δρmin = −0.13 e Å^−3
246 parameters	Extinction correction: SHELXL2014 (Sheldrick, 2015), Fc^*=kFc[1+0.001xFc^2λ^3/sin(2θ)]^-1/4
2 restraints	Extinction coefficient: 0.0073 (8)
Primary atom site location: structure-invariant direct methods	Absolute structure: Flack (1983), 1822 Friedel pairs
Secondary atom site location: difference Fourier map	Absolute structure parameter: −0.3 (8)

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
C14	0.12279 (14)	0.23661 (11)	0.98202 (7)	0.0305 (3)
H14	0.2102	0.2580	0.9526	0.037*
N1	0.16831 (11)	0.14782 (10)	1.03988 (6)	0.0315 (2)
O3	0.15911 (11)	0.40644 (9)	1.06499 (6)	0.0464 (3)
O1	−0.04242 (10)	0.16104 (10)	1.09856 (6)	0.0456 (3)
O2	−0.03638 (11)	0.41900 (9)	0.99493 (6)	0.0475 (3)
C15	0.06822 (15)	0.08188 (12)	0.88463 (7)	0.0359 (3)
H15	0.1676	0.1036	0.8684	0.043*
N2	0.01902 (12)	0.18778 (10)	0.93039 (6)	0.0321 (2)
C12	0.12463 (14)	0.00585 (12)	1.14380 (7)	0.0330 (3)
C18	0.06847 (13)	0.36261 (11)	1.01468 (7)	0.0323 (3)
C13	0.07640 (13)	0.11150 (12)	1.09329 (7)	0.0322 (3)
C1	−0.12382 (16)	0.15859 (14)	0.79537 (8)	0.0452 (3)
H1	−0.1444	0.2276	0.8279	0.054*
C6	−0.02209 (14)	0.06888 (13)	0.81452 (7)	0.0353 (3)
C9	0.19247 (18)	−0.19864 (15)	1.23588 (9)	0.0493 (4)
H9	0.2146	−0.2693	1.2669	0.059*
O5	−0.04305 (14)	−0.07267 (10)	0.96120 (7)	0.0620 (3)
C8	0.27280 (17)	−0.17514 (15)	1.17398 (9)	0.0479 (4)
H8	0.3519	−0.2288	1.1627	0.057*
C19	0.1260 (2)	0.53040 (15)	1.09662 (10)	0.0572 (4)
H19A	0.1460	0.5977	1.0602	0.086*
H19B	0.1851	0.5443	1.1407	0.086*
H19C	0.0246	0.5332	1.1104	0.086*
C7	0.23931 (16)	−0.07355 (13)	1.12783 (8)	0.0423 (3)
H7	0.2954	−0.0582	1.0849	0.051*
C4	−0.0684 (2)	−0.04241 (16)	0.70022 (9)	0.0571 (4)
H4	−0.0492	−0.1120	0.6678	0.069*
C5	0.00429 (18)	−0.03273 (15)	0.76647 (8)	0.0474 (4)
H5	0.0730	−0.0960	0.7794	0.057*
C11	0.04614 (19)	−0.01734 (17)	1.20718 (9)	0.0560 (4)
H11	−0.0316	0.0373	1.2196	0.067*
C16	0.07709 (18)	−0.04722 (14)	0.92455 (8)	0.0471 (4)
O4	0.17846 (16)	−0.11697 (13)	0.92196 (8)	0.0816 (4)
C3	−0.1684 (2)	0.04823 (18)	0.68102 (9)	0.0619 (5)
H3	−0.2179	0.0418	0.6353	0.074*
C10	0.0801 (2)	−0.11964 (19)	1.25270 (9)	0.0657 (5)
H10	0.0250	−0.1351	1.2959	0.079*
C2	−0.1965 (2)	0.14844 (17)	0.72849 (9)	0.0592 (4)
H2	−0.2660	0.2110	0.7155	0.071*
C17	−0.0486 (3)	−0.19393 (18)	1.00059 (13)	0.0933 (8)
H17A	−0.0225	−0.2637	0.9669	0.140*
H17B	−0.1458	−0.2081	1.0193	0.140*
H17C	0.0186	−0.1918	1.0421	0.140*
H1N	0.2540 (14)	0.1193 (14)	1.0386 (8)	0.039 (4)*
H2N	−0.0591 (14)	0.1679 (13)	0.9516 (7)	0.033 (4)*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
C14	0.0284 (6)	0.0311 (6)	0.0321 (6)	−0.0018 (5)	−0.0005 (5)	0.0026 (5)
N1	0.0270 (5)	0.0325 (5)	0.0352 (5)	0.0043 (4)	−0.0002 (5)	0.0039 (4)
O3	0.0447 (5)	0.0364 (5)	0.0581 (6)	0.0044 (4)	−0.0181 (5)	−0.0123 (5)
O1	0.0363 (5)	0.0549 (6)	0.0454 (5)	0.0140 (5)	0.0072 (4)	0.0097 (5)
O2	0.0412 (6)	0.0406 (5)	0.0607 (6)	0.0089 (4)	−0.0159 (5)	−0.0052 (5)
C15	0.0341 (6)	0.0374 (7)	0.0362 (7)	−0.0007 (6)	0.0017 (5)	−0.0037 (5)
N2	0.0307 (5)	0.0324 (5)	0.0332 (5)	−0.0013 (4)	−0.0016 (5)	−0.0005 (4)
C12	0.0340 (6)	0.0337 (6)	0.0314 (6)	−0.0010 (5)	−0.0040 (5)	0.0003 (5)
C18	0.0311 (6)	0.0305 (6)	0.0351 (6)	−0.0020 (5)	−0.0040 (5)	0.0042 (5)
C13	0.0322 (6)	0.0333 (6)	0.0310 (6)	0.0022 (5)	−0.0010 (5)	−0.0018 (5)
C1	0.0494 (8)	0.0441 (8)	0.0421 (7)	−0.0024 (7)	−0.0045 (7)	−0.0009 (6)
C6	0.0383 (7)	0.0365 (7)	0.0310 (6)	−0.0076 (5)	0.0033 (5)	0.0012 (5)
C9	0.0577 (9)	0.0423 (8)	0.0479 (8)	−0.0024 (7)	−0.0112 (7)	0.0134 (7)
O5	0.0676 (8)	0.0449 (6)	0.0736 (8)	−0.0110 (6)	−0.0148 (6)	0.0246 (6)
C8	0.0477 (8)	0.0397 (7)	0.0562 (9)	0.0076 (7)	−0.0043 (7)	0.0055 (7)
C19	0.0653 (10)	0.0380 (8)	0.0681 (10)	0.0046 (7)	−0.0147 (9)	−0.0170 (7)
C7	0.0429 (8)	0.0412 (7)	0.0427 (7)	0.0053 (6)	0.0041 (6)	0.0062 (6)
C4	0.0746 (11)	0.0543 (9)	0.0426 (8)	−0.0127 (9)	−0.0008 (8)	−0.0113 (7)
C5	0.0570 (9)	0.0446 (8)	0.0407 (8)	−0.0036 (7)	0.0012 (7)	−0.0050 (7)
C11	0.0566 (10)	0.0626 (10)	0.0487 (8)	0.0169 (8)	0.0150 (8)	0.0159 (8)
C16	0.0599 (9)	0.0377 (7)	0.0436 (8)	0.0078 (7)	−0.0176 (7)	−0.0074 (6)
O4	0.0964 (10)	0.0652 (8)	0.0831 (9)	0.0450 (8)	−0.0142 (8)	−0.0072 (7)
C3	0.0760 (12)	0.0700 (11)	0.0397 (8)	−0.0191 (10)	−0.0167 (8)	0.0003 (8)
C10	0.0731 (12)	0.0746 (12)	0.0494 (9)	0.0129 (10)	0.0160 (9)	0.0265 (9)
C2	0.0636 (10)	0.0595 (10)	0.0546 (10)	−0.0007 (9)	−0.0191 (8)	0.0069 (8)
C17	0.139 (2)	0.0537 (11)	0.0873 (14)	−0.0394 (13)	−0.0489 (15)	0.0349 (10)

Geometric parameters (Å, º)

C14—N2	1.4395 (16)	C9—H9	0.9500
C14—N1	1.4610 (16)	O5—C16	1.331 (2)
C14—C18	1.5277 (17)	O5—C17	1.4527 (19)
C14—H14	1.0000	C8—C7	1.385 (2)
N1—C13	1.3469 (17)	C8—H8	0.9500
N1—H1N	0.855 (13)	C19—H19A	0.9800
O3—C18	1.3246 (15)	C19—H19B	0.9800
O3—C19	1.4474 (17)	C19—H19C	0.9800
O1—C13	1.2282 (15)	C7—H7	0.9500
O2—C18	1.1973 (15)	C4—C3	1.374 (3)
C15—N2	1.4549 (16)	C4—C5	1.381 (2)
C15—C6	1.5294 (18)	C4—H4	0.9500
C15—C16	1.530 (2)	C5—H5	0.9500
C15—H15	1.0000	C11—C10	1.385 (2)
N2—H2N	0.850 (12)	C11—H11	0.9500
C12—C11	1.382 (2)	C16—O4	1.1952 (19)
C12—C7	1.3848 (19)	C3—C2	1.378 (3)
C12—C13	1.5009 (17)	C3—H3	0.9500
C1—C6	1.378 (2)	C10—H10	0.9500
C1—C2	1.392 (2)	C2—H2	0.9500
C1—H1	0.9500	C17—H17A	0.9800
C6—C5	1.393 (2)	C17—H17B	0.9800
C9—C8	1.370 (2)	C17—H17C	0.9800
C9—C10	1.369 (2)
N2—C14—N1	115.89 (10)	C9—C8—H8	119.8
N2—C14—C18	109.37 (10)	C7—C8—H8	119.8
N1—C14—C18	111.41 (10)	O3—C19—H19A	109.5
N2—C14—H14	106.5	O3—C19—H19B	109.5
N1—C14—H14	106.5	H19A—C19—H19B	109.5
C18—C14—H14	106.5	O3—C19—H19C	109.5
C13—N1—C14	120.44 (11)	H19A—C19—H19C	109.5
C13—N1—H1N	121.3 (10)	H19B—C19—H19C	109.5
C14—N1—H1N	118.2 (10)	C12—C7—C8	120.44 (14)
C18—O3—C19	116.33 (11)	C12—C7—H7	119.8
N2—C15—C6	111.39 (11)	C8—C7—H7	119.8
N2—C15—C16	114.64 (11)	C3—C4—C5	120.22 (16)
C6—C15—C16	110.07 (11)	C3—C4—H4	119.9
N2—C15—H15	106.8	C5—C4—H4	119.9
C6—C15—H15	106.8	C4—C5—C6	120.67 (15)
C16—C15—H15	106.8	C4—C5—H5	119.7
C14—N2—C15	115.15 (10)	C6—C5—H5	119.7
C14—N2—H2N	111.8 (9)	C12—C11—C10	120.44 (15)
C15—N2—H2N	110.0 (10)	C12—C11—H11	119.8
C11—C12—C7	118.61 (13)	C10—C11—H11	119.8
C11—C12—C13	118.31 (12)	O4—C16—O5	124.52 (15)
C7—C12—C13	122.99 (12)	O4—C16—C15	124.07 (16)
O2—C18—O3	123.96 (12)	O5—C16—C15	111.41 (12)
O2—C18—C14	125.39 (12)	C4—C3—C2	119.61 (15)
O3—C18—C14	110.51 (10)	C4—C3—H3	120.2
O1—C13—N1	120.90 (12)	C2—C3—H3	120.2
O1—C13—C12	122.21 (12)	C9—C10—C11	120.49 (15)
N1—C13—C12	116.86 (11)	C9—C10—H10	119.8
C6—C1—C2	120.23 (15)	C11—C10—H10	119.8
C6—C1—H1	119.9	C3—C2—C1	120.43 (16)
C2—C1—H1	119.9	C3—C2—H2	119.8
C1—C6—C5	118.82 (13)	C1—C2—H2	119.8
C1—C6—C15	121.92 (12)	O5—C17—H17A	109.5
C5—C6—C15	119.17 (12)	O5—C17—H17B	109.5
C8—C9—C10	119.61 (14)	H17A—C17—H17B	109.5
C8—C9—H9	120.2	O5—C17—H17C	109.5
C10—C9—H9	120.2	H17A—C17—H17C	109.5
C16—O5—C17	116.64 (16)	H17B—C17—H17C	109.5
C9—C8—C7	120.38 (15)
N2—C14—N1—C13	−68.46 (15)	N2—C15—C6—C5	−175.99 (12)
C18—C14—N1—C13	57.43 (15)	C16—C15—C6—C5	−47.69 (17)
N1—C14—N2—C15	−64.44 (15)	C10—C9—C8—C7	−1.2 (2)
C18—C14—N2—C15	168.63 (10)	C11—C12—C7—C8	1.0 (2)
C6—C15—N2—C14	−158.86 (11)	C13—C12—C7—C8	−175.46 (13)
C16—C15—N2—C14	75.32 (15)	C9—C8—C7—C12	0.3 (2)
C19—O3—C18—O2	−0.1 (2)	C3—C4—C5—C6	−0.3 (2)
C19—O3—C18—C14	175.61 (13)	C1—C6—C5—C4	1.1 (2)
N2—C14—C18—O2	−7.24 (17)	C15—C6—C5—C4	−175.50 (14)
N1—C14—C18—O2	−136.67 (13)	C7—C12—C11—C10	−1.4 (2)
N2—C14—C18—O3	177.07 (11)	C13—C12—C11—C10	175.25 (16)
N1—C14—C18—O3	47.65 (14)	C17—O5—C16—O4	0.2 (2)
C14—N1—C13—O1	−6.90 (19)	C17—O5—C16—C15	179.10 (13)
C14—N1—C13—C12	171.27 (10)	N2—C15—C16—O4	−131.74 (15)
C11—C12—C13—O1	−13.9 (2)	C6—C15—C16—O4	101.76 (17)
C7—C12—C13—O1	162.54 (13)	N2—C15—C16—O5	49.39 (16)
C11—C12—C13—N1	167.94 (13)	C6—C15—C16—O5	−77.11 (14)
C7—C12—C13—N1	−15.60 (19)	C5—C4—C3—C2	−0.4 (3)
C2—C1—C6—C5	−1.2 (2)	C8—C9—C10—C11	0.8 (3)
C2—C1—C6—C15	175.29 (14)	C12—C11—C10—C9	0.5 (3)
N2—C15—C6—C1	7.55 (18)	C4—C3—C2—C1	0.3 (3)
C16—C15—C6—C1	135.86 (14)	C6—C1—C2—C3	0.5 (2)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1N···O2^i	0.85 (1)	2.09 (1)	2.9147 (15)	162 (1)
N2—H2N···O5	0.85 (1)	2.52 (1)	2.8334 (15)	103 (1)
C1—H1···N2	0.95	2.44	2.8000 (18)	102
C7—H7···O2^i	0.95	2.58	3.4530 (18)	153

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