(2R,6S)-tert-Butyl 2-(benzhydryl-carbamo-yl)-6-methyl-morpholine-4-carboxyl-ate.

The title compound, C(24)H(30)N(2)O(4), was obtained by the reaction of (2R,6S)-4-(tert-but-oxy-carbon-yl)-6-methyl-morpho-line-2-carb-oxy-lic acid with diphenyl-methanamine in dimethyl-formamide solution. The morpholine ring is in a chair conformation. In the crystal, weak inter-molecular C-H⋯O hydrogen bonds link mol-ecules into chains along the b axis.

Related literature

For a review of the biological relevance and synthesis of C-substituted morpholine derivatives, see: Wijtmans et al. (2004 ▶). For applications of morpholine derivatives as drugs, see: Dando & Perry (2004 ▶); Hajos et al. (2004 ▶); Hale et al. (1998 ▶); Versiani et al. (2002 ▶). For agrochemical fungicides and bactericides containing a morpholine skeleton, see: Dieckmann et al. (1993 ▶). For applications of morpholines as chiral auxiliaries in asymmetric synthesis, see: Dave & Sasaki (2004 ▶); Enders et al. (1994 ▶).

Experimental

Crystal data

C24H30N2O4

M = 410.50

Monoclinic,

a = 27.248 (4) Å

b = 5.8241 (8) Å

c = 14.275 (2) Å

β = 94.192 (3)°

V = 2259.3 (5) Å3

Z = 4

Mo Kα radiation

μ = 0.08 mm−1

T = 293 K

0.37 × 0.24 × 0.16 mm

Data collection

Bruker SMART APEX CCD diffractometer

5956 measured reflections

2310 independent reflections

1934 reflections with I > 2σ(I)

R int = 0.110

Refinement

R[F 2 > 2σ(F 2)] = 0.048

wR(F 2) = 0.109

S = 0.96

2310 reflections

279 parameters

1 restraint

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.15 e Å−3

Δρmin = −0.23 e Å−3

Data collection: SMART (Bruker, 2002 ▶); cell refinement: SAINT (Bruker, 2002 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: SHELXTL (Sheldrick, 2008 ▶); software used to prepare material for publication: SHELXTL.

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536811017764/cv5082sup1.cif

Supplementary material file. DOI: 10.1107/S1600536811017764/cv5082Isup2.cdx

Structure factors: contains datablocks I. DOI: 10.1107/S1600536811017764/cv5082Isup3.hkl

Supplementary material file. DOI: 10.1107/S1600536811017764/cv5082Isup4.cml

Additional supplementary materials: crystallographic information; 3D view; checkCIF report

Enhanced figure: interactive version of Fig. 1

C24H30N2O4	F(000) = 880
Mr = 410.50	Dx = 1.207 Mg m−3
Monoclinic, C2	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: C 2y	Cell parameters from 2344 reflections
a = 27.248 (4) Å	θ = 5.7–47.9°
b = 5.8241 (8) Å	µ = 0.08 mm−1
c = 14.275 (2) Å	T = 293 K
β = 94.192 (3)°	Prismatic, white
V = 2259.3 (5) Å3	0.37 × 0.24 × 0.16 mm
Z = 4

Bruker SMART APEX CCD diffractometer	1934 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	Rint = 0.110
graphite	θmax = 25.5°, θmin = 2.0°
φ and ω scans	h = −32→27
5956 measured reflections	k = −6→7
2310 independent reflections	l = −17→16

Refinement on F2	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.048	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.109	H atoms treated by a mixture of independent and constrained refinement
S = 0.96	w = 1/[σ2(Fo2) + (0.0542P)2] where P = (Fo2 + 2Fc2)/3
2310 reflections	(Δ/σ)max = 0.018
279 parameters	Δρmax = 0.15 e Å−3
1 restraint	Δρmin = −0.23 e Å−3

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.

	x	y	z	Uiso*/Ueq
N1	0.38365 (9)	0.0550 (5)	−0.09403 (17)	0.0726 (8)
N2	0.32924 (10)	0.1668 (4)	0.19729 (14)	0.0582 (7)
O1	0.36972 (10)	0.4751 (5)	0.15139 (14)	0.0892 (8)
O2	0.30774 (6)	0.0299 (3)	0.02574 (11)	0.0516 (5)
O3	0.39908 (8)	0.0609 (4)	−0.24661 (13)	0.0740 (6)
O4	0.43729 (7)	0.3050 (4)	−0.14171 (13)	0.0649 (6)
C1	0.34746 (10)	0.2991 (5)	0.13400 (17)	0.0504 (6)
C2	0.34143 (9)	0.2148 (5)	0.03370 (16)	0.0484 (6)
H2	0.3284	0.3407	−0.0063	0.058*
C3	0.39051 (10)	0.1440 (7)	0.00143 (19)	0.0702 (9)
H3A	0.4125	0.2750	0.0031	0.084*
H3B	0.4051	0.0268	0.0429	0.084*
C4	0.34907 (11)	−0.1318 (6)	−0.1033 (2)	0.0677 (8)
H4A	0.3621	−0.2628	−0.0677	0.081*
H4B	0.3443	−0.1769	−0.1687	0.081*
C5	0.30039 (10)	−0.0621 (5)	−0.06807 (17)	0.0529 (7)
H5	0.2804	−0.2014	−0.0645	0.064*
C6	0.27212 (12)	0.1025 (7)	−0.13283 (19)	0.0747 (9)
H6A	0.2429	0.1509	−0.1047	0.112*
H6B	0.2632	0.0278	−0.1916	0.112*
H6C	0.2922	0.2339	−0.1435	0.112*
C7	0.33164 (10)	0.2209 (5)	0.29757 (15)	0.0528 (7)
H7	0.3432	0.3797	0.3048	0.063*
C8	0.28101 (10)	0.2103 (5)	0.33392 (16)	0.0512 (6)
C9	0.25146 (10)	0.0219 (6)	0.31751 (19)	0.0610 (7)
H9	0.2632	−0.1026	0.2850	0.073*
C10	0.20460 (11)	0.0133 (7)	0.3483 (2)	0.0739 (9)
H10	0.1847	−0.1143	0.3353	0.089*
C11	0.18741 (13)	0.1950 (8)	0.3985 (2)	0.0795 (10)
H11	0.1558	0.1915	0.4192	0.095*
C12	0.21685 (14)	0.3780 (8)	0.4174 (2)	0.0825 (11)
H12	0.2056	0.4985	0.4529	0.099*
C13	0.26342 (13)	0.3900 (6)	0.38514 (18)	0.0684 (8)
H13	0.2829	0.5189	0.3979	0.082*
C14	0.36812 (9)	0.0700 (5)	0.35412 (16)	0.0486 (6)
C15	0.38313 (10)	0.1338 (6)	0.44504 (18)	0.0625 (8)
H15	0.3716	0.2702	0.4692	0.075*
C16	0.41486 (12)	−0.0017 (8)	0.5002 (2)	0.0775 (10)
H16	0.4245	0.0440	0.5612	0.093*
C17	0.43244 (11)	−0.2042 (8)	0.4660 (3)	0.0787 (10)
H17	0.4539	−0.2958	0.5033	0.094*
C18	0.41775 (11)	−0.2685 (7)	0.3760 (2)	0.0744 (9)
H18	0.4293	−0.4051	0.3521	0.089*
C19	0.38604 (11)	−0.1329 (6)	0.32084 (19)	0.0606 (7)
H19	0.3765	−0.1792	0.2599	0.073*
C20	0.40627 (10)	0.1365 (5)	−0.16836 (19)	0.0562 (7)
C21	0.47203 (10)	0.3996 (5)	−0.20592 (19)	0.0570 (7)
C22	0.49962 (12)	0.5747 (6)	−0.1450 (2)	0.0765 (9)
H22A	0.4769	0.6863	−0.1239	0.115*
H22B	0.5235	0.6500	−0.1805	0.115*
H22C	0.5160	0.4996	−0.0916	0.115*
C23	0.50568 (12)	0.2101 (6)	−0.2339 (3)	0.0787 (10)
H23A	0.5194	0.1329	−0.1786	0.118*
H23B	0.5317	0.2743	−0.2674	0.118*
H23C	0.4873	0.1025	−0.2735	0.118*
C24	0.44503 (13)	0.5127 (7)	−0.2886 (2)	0.0795 (9)
H24A	0.4274	0.3987	−0.3262	0.119*
H24B	0.4681	0.5892	−0.3256	0.119*
H24C	0.4222	0.6228	−0.2670	0.119*
H2A	0.3113 (11)	0.060 (6)	0.181 (2)	0.058 (9)*

	U11	U22	U33	U12	U13	U23
N1	0.0724 (14)	0.096 (2)	0.0528 (13)	−0.0328 (16)	0.0287 (11)	−0.0251 (14)
N2	0.0865 (17)	0.0596 (16)	0.0294 (10)	−0.0232 (15)	0.0104 (10)	−0.0025 (11)
O1	0.1344 (19)	0.0868 (17)	0.0501 (11)	−0.0546 (17)	0.0324 (12)	−0.0172 (11)
O2	0.0594 (10)	0.0633 (12)	0.0333 (8)	−0.0150 (10)	0.0120 (7)	0.0012 (8)
O3	0.0932 (14)	0.0820 (16)	0.0498 (11)	−0.0177 (13)	0.0264 (10)	−0.0213 (11)
O4	0.0692 (11)	0.0794 (14)	0.0489 (10)	−0.0184 (12)	0.0226 (9)	−0.0078 (10)
C1	0.0606 (15)	0.0540 (16)	0.0374 (13)	−0.0084 (14)	0.0102 (11)	0.0000 (12)
C2	0.0617 (14)	0.0529 (15)	0.0318 (12)	−0.0124 (13)	0.0101 (10)	0.0041 (12)
C3	0.0651 (16)	0.104 (3)	0.0432 (14)	−0.0235 (18)	0.0182 (12)	−0.0143 (16)
C4	0.0791 (19)	0.066 (2)	0.0606 (17)	−0.0091 (17)	0.0238 (14)	−0.0143 (16)
C5	0.0658 (15)	0.0556 (17)	0.0388 (13)	−0.0199 (14)	0.0129 (11)	−0.0045 (12)
C6	0.086 (2)	0.091 (2)	0.0453 (15)	−0.010 (2)	−0.0075 (14)	−0.0075 (17)
C7	0.0807 (17)	0.0498 (15)	0.0284 (11)	−0.0124 (14)	0.0080 (11)	−0.0035 (12)
C8	0.0711 (16)	0.0536 (16)	0.0291 (11)	0.0047 (14)	0.0055 (11)	0.0035 (12)
C9	0.0695 (17)	0.0628 (19)	0.0515 (15)	0.0025 (17)	0.0093 (13)	−0.0056 (14)
C10	0.0677 (18)	0.091 (2)	0.0636 (18)	0.000 (2)	0.0090 (15)	0.0064 (19)
C11	0.073 (2)	0.104 (3)	0.0630 (19)	0.024 (2)	0.0158 (16)	0.008 (2)
C12	0.104 (3)	0.088 (3)	0.0577 (18)	0.035 (2)	0.0246 (17)	−0.002 (2)
C13	0.102 (2)	0.0628 (19)	0.0417 (14)	0.0082 (19)	0.0094 (15)	−0.0034 (15)
C14	0.0553 (13)	0.0569 (17)	0.0355 (12)	−0.0131 (13)	0.0173 (10)	−0.0044 (12)
C15	0.0768 (18)	0.072 (2)	0.0391 (13)	−0.0027 (17)	0.0048 (13)	−0.0101 (14)
C16	0.079 (2)	0.101 (3)	0.0518 (17)	−0.007 (2)	−0.0050 (15)	−0.0046 (19)
C17	0.0581 (17)	0.105 (3)	0.074 (2)	0.007 (2)	0.0088 (15)	0.018 (2)
C18	0.0694 (18)	0.078 (2)	0.079 (2)	0.0090 (18)	0.0257 (16)	0.0008 (19)
C19	0.0711 (17)	0.0677 (19)	0.0446 (14)	−0.0044 (16)	0.0152 (12)	−0.0072 (15)
C20	0.0553 (14)	0.0636 (17)	0.0517 (16)	−0.0059 (14)	0.0183 (12)	−0.0122 (14)
C21	0.0616 (16)	0.0558 (16)	0.0564 (15)	0.0001 (14)	0.0221 (12)	0.0089 (14)
C22	0.0780 (19)	0.074 (2)	0.079 (2)	−0.0112 (19)	0.0170 (16)	0.0076 (19)
C23	0.0762 (19)	0.067 (2)	0.097 (3)	0.0062 (19)	0.0353 (17)	0.007 (2)
C24	0.102 (2)	0.071 (2)	0.0663 (19)	0.007 (2)	0.0086 (17)	0.0084 (17)

N1—C20	1.352 (4)	C9—H9	0.9300
N1—C4	1.439 (4)	C10—C11	1.379 (5)
N1—C3	1.457 (3)	C10—H10	0.9300
N2—C1	1.312 (3)	C11—C12	1.349 (6)
N2—C7	1.463 (3)	C11—H11	0.9300
N2—H2A	0.81 (3)	C12—C13	1.383 (5)
O1—C1	1.207 (4)	C12—H12	0.9300
O2—C2	1.414 (3)	C13—H13	0.9300
O2—C5	1.443 (3)	C14—C19	1.376 (4)
O3—C20	1.203 (3)	C14—C15	1.383 (3)
O4—C20	1.332 (3)	C15—C16	1.375 (5)
O4—C21	1.472 (3)	C15—H15	0.9300
C1—C2	1.511 (3)	C16—C17	1.376 (6)
C2—C3	1.503 (4)	C16—H16	0.9300
C2—H2	0.9800	C17—C18	1.369 (5)
C3—H3A	0.9700	C17—H17	0.9300
C3—H3B	0.9700	C18—C19	1.376 (4)
C4—C5	1.508 (4)	C18—H18	0.9300
C4—H4A	0.9700	C19—H19	0.9300
C4—H4B	0.9700	C21—C24	1.497 (4)
C5—C6	1.504 (4)	C21—C22	1.505 (5)
C5—H5	0.9800	C21—C23	1.507 (4)
C6—H6A	0.9600	C22—H22A	0.9600
C6—H6B	0.9600	C22—H22B	0.9600
C6—H6C	0.9600	C22—H22C	0.9600
C7—C8	1.510 (4)	C23—H23A	0.9600
C7—C14	1.515 (4)	C23—H23B	0.9600
C7—H7	0.9800	C23—H23C	0.9600
C8—C9	1.371 (4)	C24—H24A	0.9600
C8—C13	1.382 (4)	C24—H24B	0.9600
C9—C10	1.382 (4)	C24—H24C	0.9600
C20—N1—C4	121.8 (2)	C9—C10—H10	120.2
C20—N1—C3	125.1 (3)	C12—C11—C10	119.4 (3)
C4—N1—C3	113.2 (2)	C12—C11—H11	120.3
C1—N2—C7	123.7 (2)	C10—C11—H11	120.3
C1—N2—H2A	120 (2)	C11—C12—C13	121.3 (3)
C7—N2—H2A	115 (2)	C11—C12—H12	119.4
C2—O2—C5	113.74 (17)	C13—C12—H12	119.4
C20—O4—C21	121.4 (2)	C8—C13—C12	120.0 (4)
O1—C1—N2	124.5 (2)	C8—C13—H13	120.0
O1—C1—C2	119.3 (2)	C12—C13—H13	120.0
N2—C1—C2	116.1 (2)	C19—C14—C15	117.8 (3)
O2—C2—C3	110.7 (2)	C19—C14—C7	123.3 (2)
O2—C2—C1	110.40 (19)	C15—C14—C7	118.8 (2)
C3—C2—C1	110.0 (2)	C16—C15—C14	120.9 (3)
O2—C2—H2	108.6	C16—C15—H15	119.6
C3—C2—H2	108.6	C14—C15—H15	119.6
C1—C2—H2	108.6	C15—C16—C17	120.6 (3)
N1—C3—C2	109.1 (2)	C15—C16—H16	119.7
N1—C3—H3A	109.9	C17—C16—H16	119.7
C2—C3—H3A	109.9	C18—C17—C16	118.8 (3)
N1—C3—H3B	109.9	C18—C17—H17	120.6
C2—C3—H3B	109.9	C16—C17—H17	120.6
H3A—C3—H3B	108.3	C17—C18—C19	120.6 (3)
N1—C4—C5	110.6 (3)	C17—C18—H18	119.7
N1—C4—H4A	109.5	C19—C18—H18	119.7
C5—C4—H4A	109.5	C18—C19—C14	121.3 (3)
N1—C4—H4B	109.5	C18—C19—H19	119.4
C5—C4—H4B	109.5	C14—C19—H19	119.4
H4A—C4—H4B	108.1	O3—C20—O4	126.3 (3)
O2—C5—C6	111.3 (2)	O3—C20—N1	123.2 (3)
O2—C5—C4	110.1 (2)	O4—C20—N1	110.5 (2)
C6—C5—C4	112.9 (2)	O4—C21—C24	110.7 (2)
O2—C5—H5	107.4	O4—C21—C22	102.1 (2)
C6—C5—H5	107.4	C24—C21—C22	110.7 (3)
C4—C5—H5	107.4	O4—C21—C23	108.8 (2)
C5—C6—H6A	109.5	C24—C21—C23	112.8 (3)
C5—C6—H6B	109.5	C22—C21—C23	111.2 (3)
H6A—C6—H6B	109.5	C21—C22—H22A	109.5
C5—C6—H6C	109.5	C21—C22—H22B	109.5
H6A—C6—H6C	109.5	H22A—C22—H22B	109.5
H6B—C6—H6C	109.5	C21—C22—H22C	109.5
N2—C7—C8	110.5 (2)	H22A—C22—H22C	109.5
N2—C7—C14	112.2 (2)	H22B—C22—H22C	109.5
C8—C7—C14	111.9 (2)	C21—C23—H23A	109.5
N2—C7—H7	107.3	C21—C23—H23B	109.5
C8—C7—H7	107.3	H23A—C23—H23B	109.5
C14—C7—H7	107.3	C21—C23—H23C	109.5
C9—C8—C13	118.3 (3)	H23A—C23—H23C	109.5
C9—C8—C7	120.9 (2)	H23B—C23—H23C	109.5
C13—C8—C7	120.8 (3)	C21—C24—H24A	109.5
C8—C9—C10	121.3 (3)	C21—C24—H24B	109.5
C8—C9—H9	119.4	H24A—C24—H24B	109.5
C10—C9—H9	119.4	C21—C24—H24C	109.5
C11—C10—C9	119.6 (4)	H24A—C24—H24C	109.5
C11—C10—H10	120.2	H24B—C24—H24C	109.5
C7—N2—C1—O1	2.9 (5)	C9—C10—C11—C12	−0.5 (5)
C7—N2—C1—C2	−180.0 (2)	C10—C11—C12—C13	1.9 (5)
C5—O2—C2—C3	−57.3 (3)	C9—C8—C13—C12	−0.8 (4)
C5—O2—C2—C1	−179.4 (2)	C7—C8—C13—C12	179.6 (2)
O1—C1—C2—O2	−170.2 (3)	C11—C12—C13—C8	−1.3 (5)
N2—C1—C2—O2	12.4 (3)	N2—C7—C14—C19	−17.3 (3)
O1—C1—C2—C3	67.3 (4)	C8—C7—C14—C19	107.6 (3)
N2—C1—C2—C3	−110.0 (3)	N2—C7—C14—C15	165.0 (2)
C20—N1—C3—C2	123.2 (3)	C8—C7—C14—C15	−70.1 (3)
C4—N1—C3—C2	−56.1 (4)	C19—C14—C15—C16	−0.1 (4)
O2—C2—C3—N1	55.5 (3)	C7—C14—C15—C16	177.8 (3)
C1—C2—C3—N1	177.8 (3)	C14—C15—C16—C17	0.0 (5)
C20—N1—C4—C5	−124.0 (3)	C15—C16—C17—C18	0.0 (5)
C3—N1—C4—C5	55.3 (4)	C16—C17—C18—C19	0.1 (5)
C2—O2—C5—C6	−70.7 (3)	C17—C18—C19—C14	−0.2 (4)
C2—O2—C5—C4	55.4 (3)	C15—C14—C19—C18	0.1 (4)
N1—C4—C5—O2	−52.7 (3)	C7—C14—C19—C18	−177.6 (3)
N1—C4—C5—C6	72.4 (3)	C21—O4—C20—O3	−8.3 (4)
C1—N2—C7—C8	126.8 (3)	C21—O4—C20—N1	170.6 (3)
C1—N2—C7—C14	−107.5 (3)	C4—N1—C20—O3	0.4 (5)
N2—C7—C8—C9	51.2 (3)	C3—N1—C20—O3	−178.8 (3)
C14—C7—C8—C9	−74.6 (3)	C4—N1—C20—O4	−178.5 (3)
N2—C7—C8—C13	−129.2 (3)	C3—N1—C20—O4	2.3 (4)
C14—C7—C8—C13	105.0 (3)	C20—O4—C21—C24	63.9 (4)
C13—C8—C9—C10	2.1 (4)	C20—O4—C21—C22	−178.2 (2)
C7—C8—C9—C10	−178.2 (2)	C20—O4—C21—C23	−60.5 (3)
C8—C9—C10—C11	−1.5 (4)

D—H···A	D—H	H···A	D···A	D—H···A
C19—H19···O1i	0.93	2.54	3.332 (4)	144

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C19—H19⋯O1i	0.93	2.54	3.332 (4)	144

Symmetry code: (i) .