3-[(2R*,3S*)-3-(2-Methoxy­anilino)-2-methyl-3-phenyl­propionyl]­spiro­[2H-1,3-benzoxazine-2,1′-cyclo­hexan]-4(3H)-one

The racemic title compound, C₃₀H₃₂N₂O₄, was synthesized from spiro­[2H-1,3-benzoxazine-2,1′-cyclo­hexan]-4(3H)-one and N-benzyl­idene-2-methoxy­benzen­amine under classical Reformatsky reaction conditions. Intermolecular N—H...O and C—H...O hydrogen bonds link the mol­ecules in the crystal structure into infinite chains along the a axis. These chains form layers parallel to the (001) plane, which are stabilized by weak interlayer C—H...O hydrogen bonds.

Key indicators

• Single-crystal X-ray study
• T = 295 K
• Mean [sigma](C-C) = 0.003 Å
• R factor = 0.031
• wR factor = 0.063
• Data-to-parameter ratio = 8.0

checkCIF/PLATON results

No syntax errors found



Alert level B
REFNR01_ALERT_3_B  Ratio of reflections to parameters is < 8 for a
            centrosymmetric structure
            sine(theta)/lambda                0.6493
            Proportion of unique data used    0.4573
            Ratio reflections to parameters   7.9877
PLAT088_ALERT_3_B Poor Data / Parameter Ratio ....................       7.99
PLAT230_ALERT_2_B Hirshfeld Test Diff for    C4     -   C5      ..       7.19 su

Alert level C
PLAT026_ALERT_3_C Ratio Observed / Unique Reflections too Low ....         46 Perc.
PLAT230_ALERT_2_C Hirshfeld Test Diff for    C5     -   C10     ..       5.34 su
PLAT410_ALERT_2_C Short Intra H...H Contact  H19    ..  H20     ..       1.98 Ang.
PLAT480_ALERT_4_C Long H...A H-Bond Reported H24    ..  O2      ..       2.69 Ang.

   0 ALERT level A = In general: serious problem
   3 ALERT level B = Potentially serious problem
   4 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
   3 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
   1 ALERT type 4 Improvement, methodology, query or suggestion

---

Computing details

Data collection: PROCESS-AUTO (V1.06; Rigaku,1998); cell refinement: PROCESS-AUTO (V1.06; Rigaku,1998); data reduction: CrystalStructure (Version 3.60; Rigaku/MSC, 2004); program(s) used to solve structure: SHELXS97 (Sheldrick,1997); program(s) used to refine structure: CRYSTALS (Watkin,1996); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997); software used to prepare material for publication: CrystalStructure (Version 3.60; Rigaku/MSC, 2004).

(3)

Crystal data

C30H32N2O4	F(000) = 2064.00
Mr = 484.59	Dx = 1.265 Mg m^−3
Orthorhombic, Pbcn	Mo Kα radiation, λ = 0.7107 Å
Hall symbol: -P 2n 2ab	Cell parameters from 42864 reflections
a = 24.1025 (4) Å	θ = 1.4–27.5°
b = 11.0675 (5) Å	µ = 0.08 mm^−1
c = 19.0716 (2) Å	T = 295 K
V = 5087.4 (3) Å^3	Platelet, colorless
Z = 8	0.16 × 0.10 × 0.08 mm

Data collection

Rigaku R-AXIS RAPID diffractometer	Rint = 0.061
Detector resolution: 10.00 pixels mm^-1	θmax = 27.5°
ω scans	h = −31→31
43304 measured reflections	k = −14→12
5694 independent reflections	l = −24→24
2604 reflections with F^2 > 2σ(F^2)

Refinement

Refinement on F^2	w = 1/[0.0003Fo^2 + σ(Fo^2)]/(4Fo^2)
R[F^2 > 2σ(F^2)] = 0.031	(Δ/σ)max < 0.001
wR(F^2) = 0.063	Δρmax = 0.12 e Å^−3
S = 1.03	Δρmin = −0.13 e Å^−3
2604 reflections	Extinction correction: Larson (1970), equation 22
326 parameters	Extinction coefficient: 240 (30)
H-atom parameters constrained

Special details

Geometry. ENTER SPECIAL DETAILS OF THE MOLECULAR GEOMETRY

Refinement. Refinement using reflections with F² > 2.0 σ(F²). The weighted R-factor (wR) and goodness of fit (S) are based on F². R-factor (gt) are based on F. The threshold expression of F² > 2.0 σ(F²) is used only for calculating R-factor (gt).

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Ų)

	x	y	z	Uiso*/Ueq
O1	0.27996 (5)	0.4327 (1)	0.52383 (7)	0.0506 (4)
O2	0.34131 (6)	0.6213 (1)	0.66668 (7)	0.0662 (5)
O3	0.39588 (5)	0.7081 (1)	0.47564 (6)	0.0464 (4)
O4	0.21313 (6)	0.7781 (1)	0.38113 (6)	0.0518 (4)
N1	0.33472 (6)	0.5973 (1)	0.54790 (7)	0.0401 (5)
N2	0.19778 (6)	0.6412 (1)	0.49153 (7)	0.0402 (5)
C1	0.23960 (7)	0.5750 (2)	0.60232 (8)	0.0395 (6)
C2	0.23057 (8)	0.4904 (2)	0.66468 (9)	0.0558 (7)
C3	0.28531 (8)	0.5270 (2)	0.55551 (9)	0.0397 (6)
C4	0.36077 (9)	0.6394 (2)	0.6087 (1)	0.0456 (6)
C5	0.41308 (8)	0.7045 (2)	0.5983 (1)	0.0429 (6)
C6	0.44631 (9)	0.7365 (2)	0.6547 (1)	0.0549 (7)
C7	0.4946 (1)	0.8001 (2)	0.6440 (1)	0.0641 (8)
C8	0.5096 (1)	0.8327 (2)	0.5766 (1)	0.0688 (8)
C9	0.47716 (9)	0.8022 (2)	0.5199 (1)	0.0611 (7)
C10	0.42913 (9)	0.7370 (2)	0.5316 (1)	0.0455 (6)
C11	0.36787 (8)	0.5932 (2)	0.48079 (9)	0.0398 (6)
C12	0.33090 (8)	0.5902 (2)	0.41643 (9)	0.0491 (6)
C13	0.36601 (9)	0.5913 (2)	0.34962 (9)	0.0579 (7)
C14	0.4087 (1)	0.4899 (2)	0.3493 (1)	0.0644 (8)
C15	0.44490 (9)	0.4938 (2)	0.4145 (1)	0.0585 (7)
C16	0.40958 (8)	0.4905 (2)	0.4807 (1)	0.0473 (6)
C17	0.18638 (7)	0.5814 (2)	0.55805 (9)	0.0386 (6)
C18	0.17226 (7)	0.6061 (2)	0.42943 (9)	0.0367 (5)
C19	0.14137 (8)	0.5010 (2)	0.4213 (1)	0.0470 (6)
C20	0.11824 (9)	0.4704 (2)	0.3570 (1)	0.0549 (7)
C21	0.12547 (9)	0.5441 (2)	0.3001 (1)	0.0586 (7)
C22	0.15698 (9)	0.6488 (2)	0.3064 (1)	0.0517 (7)
C23	0.18059 (8)	0.6782 (2)	0.36964 (9)	0.0404 (6)
C24	0.2372 (1)	0.8353 (2)	0.3218 (1)	0.0641 (8)
C25	0.13857 (9)	0.6371 (2)	0.59816 (9)	0.0420 (6)
C26	0.09107 (9)	0.5725 (2)	0.6124 (1)	0.0552 (7)
C27	0.0474 (1)	0.6241 (3)	0.6487 (1)	0.0738 (9)
C28	0.0507 (1)	0.7410 (3)	0.6704 (1)	0.080 (1)
C29	0.0977 (1)	0.8069 (2)	0.6579 (1)	0.083 (1)
C30	0.1416 (1)	0.7551 (2)	0.6219 (1)	0.0653 (8)
H1	0.2494	0.6558	0.6193	0.047*
H2	0.2022	0.5233	0.6943	0.067*
H3	0.2190	0.4128	0.6475	0.067*
H4	0.2645	0.4826	0.6906	0.067*
H5	0.4353	0.7137	0.7024	0.066*
H6	0.5181	0.8224	0.6839	0.077*
H7	0.5440	0.8782	0.5690	0.082*
H8	0.4879	0.8261	0.4724	0.073*
H9	0.3069	0.6604	0.4167	0.059*
H10	0.3085	0.5174	0.4174	0.059*
H11	0.3417	0.5818	0.3094	0.069*
H12	0.3853	0.6681	0.3464	0.069*
H13	0.3894	0.4130	0.3477	0.077*
H14	0.4320	0.4979	0.3081	0.077*
H15	0.4696	0.4245	0.4144	0.070*
H16	0.4667	0.5675	0.4140	0.070*
H17	0.3899	0.4142	0.4829	0.057*
H18	0.4335	0.4981	0.5214	0.057*
H19	0.1758	0.4980	0.5472	0.046*
H20	0.1357	0.4477	0.4617	0.056*
H21	0.0969	0.3955	0.3523	0.066*
H22	0.1083	0.5234	0.2551	0.070*
H23	0.1623	0.7015	0.2656	0.062*
H24	0.2080	0.8678	0.2932	0.077*
H25	0.2585	0.7774	0.2956	0.077*
H26	0.2607	0.8997	0.3377	0.077*
H27	0.0882	0.4885	0.5966	0.066*
H28	0.0139	0.5769	0.6588	0.089*
H29	0.0194	0.7781	0.6954	0.096*
H30	0.1003	0.8909	0.6740	0.099*
H31	0.1752	0.8025	0.6131	0.078*
H32	0.2078	0.7193	0.4953	0.048*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
O1	0.0509 (9)	0.0468 (8)	0.0542 (8)	−0.0017 (8)	0.0023 (7)	−0.0059 (7)
O2	0.051 (1)	0.109 (1)	0.0379 (8)	−0.0198 (9)	0.0023 (7)	−0.0050 (8)
O3	0.0473 (9)	0.0453 (8)	0.0467 (8)	−0.0034 (7)	0.0030 (7)	0.0016 (6)
O4	0.066 (1)	0.0517 (9)	0.0379 (7)	−0.0089 (8)	0.0025 (7)	0.0065 (7)
N1	0.032 (1)	0.053 (1)	0.0362 (9)	−0.0028 (9)	0.0025 (7)	−0.0031 (7)
N2	0.044 (1)	0.0429 (9)	0.0340 (8)	−0.0080 (8)	0.0004 (8)	0.0018 (7)
C1	0.035 (1)	0.047 (1)	0.036 (1)	−0.004 (1)	0.0031 (9)	−0.0004 (9)
C2	0.048 (1)	0.076 (1)	0.043 (1)	−0.002 (1)	0.001 (1)	0.012 (1)
C3	0.037 (1)	0.047 (1)	0.035 (1)	0.000 (1)	−0.003 (1)	0.005 (1)
C4	0.039 (1)	0.058 (1)	0.040 (1)	0.003 (1)	0.000 (1)	−0.005 (1)
C5	0.033 (1)	0.049 (1)	0.047 (1)	−0.001 (1)	0.002 (1)	−0.007 (1)
C6	0.043 (1)	0.066 (1)	0.055 (1)	0.000 (1)	−0.004 (1)	−0.012 (1)
C7	0.043 (2)	0.072 (2)	0.077 (2)	−0.006 (1)	−0.008 (1)	−0.018 (1)
C8	0.044 (2)	0.067 (2)	0.096 (2)	−0.016 (1)	0.006 (2)	−0.014 (1)
C9	0.053 (2)	0.060 (1)	0.070 (2)	−0.013 (1)	0.012 (1)	−0.006 (1)
C10	0.038 (1)	0.043 (1)	0.055 (1)	0.000 (1)	0.001 (1)	−0.007 (1)
C11	0.036 (1)	0.044 (1)	0.039 (1)	−0.001 (1)	0.0049 (9)	−0.0008 (9)
C12	0.045 (1)	0.061 (1)	0.041 (1)	0.002 (1)	−0.001 (1)	−0.000 (1)
C13	0.061 (2)	0.074 (1)	0.039 (1)	−0.005 (1)	0.005 (1)	−0.003 (1)
C14	0.065 (2)	0.075 (2)	0.053 (1)	−0.002 (1)	0.018 (1)	−0.014 (1)
C15	0.048 (1)	0.062 (1)	0.065 (1)	0.009 (1)	0.013 (1)	−0.009 (1)
C16	0.042 (1)	0.049 (1)	0.050 (1)	0.003 (1)	0.001 (1)	−0.003 (1)
C17	0.035 (1)	0.044 (1)	0.037 (1)	−0.005 (1)	0.0018 (9)	0.0034 (9)
C18	0.029 (1)	0.042 (1)	0.038 (1)	0.006 (1)	−0.0012 (9)	−0.0050 (9)
C19	0.041 (1)	0.051 (1)	0.049 (1)	−0.001 (1)	−0.000 (1)	−0.003 (1)
C20	0.043 (1)	0.061 (1)	0.061 (1)	−0.002 (1)	−0.002 (1)	−0.017 (1)
C21	0.047 (2)	0.082 (2)	0.046 (1)	0.008 (1)	−0.006 (1)	−0.022 (1)
C22	0.050 (1)	0.068 (1)	0.037 (1)	0.008 (1)	−0.001 (1)	−0.004 (1)
C23	0.040 (1)	0.044 (1)	0.037 (1)	0.007 (1)	0.002 (1)	−0.0025 (9)
C24	0.067 (2)	0.072 (2)	0.054 (1)	−0.005 (1)	0.009 (1)	0.013 (1)
C25	0.038 (1)	0.052 (1)	0.036 (1)	0.002 (1)	0.001 (1)	0.0070 (9)
C26	0.038 (1)	0.073 (2)	0.054 (1)	−0.004 (1)	0.002 (1)	0.004 (1)
C27	0.041 (2)	0.112 (2)	0.068 (2)	0.005 (2)	0.013 (1)	0.014 (2)
C28	0.070 (2)	0.113 (2)	0.057 (2)	0.035 (2)	0.025 (1)	0.013 (2)
C29	0.103 (2)	0.071 (2)	0.075 (2)	0.021 (2)	0.030 (2)	0.001 (1)
C30	0.067 (2)	0.057 (1)	0.072 (1)	−0.000 (1)	0.026 (1)	0.001 (1)

Geometric parameters (Å, º)

O1—C3	1.213 (2)	C26—C27	1.385 (3)
O2—C4	1.219 (2)	C27—C28	1.361 (4)
O3—C10	1.372 (2)	C28—C29	1.369 (4)
O3—C11	1.443 (2)	C29—C30	1.386 (4)
O4—C23	1.374 (2)	N2—H32	0.9013
O4—C24	1.420 (2)	C1—H1	0.9800
N1—C3	1.430 (2)	C2—H2	0.9600
N1—C4	1.398 (2)	C2—H3	0.9600
N1—C11	1.510 (2)	C2—H4	0.9600
N2—C17	1.457 (2)	C6—H5	0.9800
N2—C18	1.390 (2)	C7—H6	0.9800
C1—C2	1.530 (2)	C8—H7	0.9800
C1—C3	1.514 (2)	C9—H8	0.9800
C1—C17	1.537 (2)	C12—H9	0.9700
C4—C5	1.465 (3)	C12—H10	0.9700
C5—C6	1.388 (3)	C13—H11	0.9700
C5—C10	1.377 (3)	C13—H12	0.9700
C6—C7	1.376 (3)	C14—H13	0.9700
C7—C8	1.383 (4)	C14—H14	0.9700
C8—C9	1.376 (3)	C15—H15	0.9700
C9—C10	1.382 (3)	C15—H16	0.9700
C11—C12	1.517 (3)	C16—H17	0.9700
C11—C16	1.517 (3)	C16—H18	0.9700
C12—C13	1.530 (3)	C17—H19	0.9800
C13—C14	1.522 (3)	C19—H20	0.9800
C14—C15	1.520 (3)	C20—H21	0.9800
C15—C16	1.524 (3)	C21—H22	0.9800
C17—C25	1.514 (3)	C22—H23	0.9800
C18—C19	1.390 (3)	C24—H24	0.9600
C18—C23	1.406 (2)	C24—H25	0.9600
C19—C20	1.389 (3)	C24—H26	0.9600
C20—C21	1.369 (3)	C26—H27	0.9800
C21—C22	1.390 (3)	C27—H28	0.9800
C22—C23	1.374 (3)	C28—H29	0.9800
C25—C26	1.377 (3)	C29—H30	0.9800
C25—C30	1.385 (3)	C30—H31	0.9800
O1—C3—N1	120.4 (2)	C1—C2—H3	108.8921
O1—C3—C1	121.2 (2)	C1—C2—H4	109.4943
O2—C4—N1	121.7 (2)	C1—C2—H2	109.0277
O2—C4—C5	122.3 (2)	H1—C1—C3	109.8859
C11—O3—C10	115.2 (1)	H1—C1—C17	109.9184
O3—C10—C5	119.5 (2)	C1—C17—H19	106.8730
O3—C10—C9	119.1 (2)	H3—C2—H2	109.4662
O3—C11—N1	106.2 (1)	H4—C2—H2	109.8103
O3—C11—C12	103.8 (1)	H4—C2—H3	110.1273
O3—C11—C16	110.5 (1)	C5—C6—H5	119.7758
O4—C23—C18	114.1 (1)	H5—C6—C7	120.0105
O4—C23—C22	124.6 (2)	C6—C7—H6	120.1564
C24—O4—C23	117.7 (1)	H6—C7—C8	120.2846
N1—C3—C1	118.3 (2)	C7—C8—H7	119.4727
C4—N1—C3	118.1 (1)	C8—C9—H8	120.7202
C11—N1—C3	120.7 (1)	H7—C8—C9	119.3863
C11—N1—C4	118.4 (1)	H8—C9—C10	120.7192
N1—C4—C5	116.0 (2)	C11—C12—H9	109.2003
N1—C11—C12	112.1 (1)	C11—C12—H10	109.2654
N1—C11—C16	112.0 (1)	C11—C16—H17	109.1183
N2—C17—C1	110.0 (1)	C11—C16—H18	109.1683
C18—N2—C17	122.1 (1)	H9—C12—C13	109.1756
N2—C17—C25	113.5 (1)	H10—C12—C13	109.3070
N2—C18—C23	118.0 (2)	C12—C13—H12	109.0038
N2—C18—C19	124.4 (2)	C12—C13—H11	108.8865
C3—C1—C2	110.3 (1)	H10—C12—H9	109.4619
C17—C1—C2	109.7 (1)	H12—C13—C14	108.7971
C17—C1—C3	107.4 (1)	H11—C13—C14	108.8719
C1—C17—C25	112.1 (1)	C13—C14—H13	108.9042
C4—C5—C6	121.1 (2)	C13—C14—H14	109.1931
C4—C5—C10	119.7 (2)	H12—C13—H11	109.4707
C10—C5—C6	119.2 (2)	C14—C15—H16	109.0600
C5—C6—C7	120.2 (2)	H13—C14—C15	108.9645
C5—C10—C9	121.3 (2)	C14—C15—H15	109.2130
C6—C7—C8	119.6 (2)	H14—C14—C15	108.9805
C7—C8—C9	121.1 (2)	H14—C14—H13	109.4647
C8—C9—C10	118.6 (2)	C15—C16—H17	109.2652
C16—C11—C12	111.8 (2)	H16—C15—C16	109.2597
C11—C12—C13	110.4 (2)	C15—C16—H18	109.1555
C11—C16—C15	110.7 (2)	H15—C15—C16	108.9308
C12—C13—C14	111.8 (2)	H16—C15—H15	109.4599
C13—C14—C15	111.3 (2)	H18—C16—H17	109.4600
C14—C15—C16	110.9 (2)	H19—C17—C25	106.9568
C17—C25—C26	121.4 (2)	C18—C19—H20	119.3255
C17—C25—C30	120.6 (2)	H20—C19—C20	119.5263
C23—C18—C19	117.5 (2)	C19—C20—H21	119.8475
C18—C19—C20	121.1 (2)	H21—C20—C21	119.9124
C18—C23—C22	121.3 (2)	C20—C21—H22	120.0829
C19—C20—C21	120.2 (2)	C21—C22—H23	120.0296
C20—C21—C22	119.9 (2)	H22—C21—C22	120.0205
C21—C22—C23	119.9 (2)	H23—C22—C23	120.0389
C30—C25—C26	118.0 (2)	H25—C24—H24	110.2100
C25—C26—C27	121.1 (2)	H26—C24—H24	109.4649
C25—C30—C29	120.8 (2)	H26—C24—H25	110.2145
C26—C27—C28	120.0 (2)	C25—C26—H27	119.4555
C27—C28—C29	120.1 (3)	C25—C30—H31	119.5364
C28—C29—C30	119.9 (2)	H27—C26—C27	119.4173
O4—C24—H24	108.6993	C26—C27—H28	120.2497
O4—C24—H25	109.5754	H28—C27—C28	119.7180
O4—C24—H26	108.6413	C27—C28—H29	120.0867
N2—C17—H19	107.0319	C28—C29—H30	120.2401
H32—N2—C17	114.6157	H29—C28—C29	119.7730
H32—N2—C18	117.0572	C29—C30—H31	119.6828
H1—C1—C2	109.6349	H30—C29—C30	119.8634

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
N2—H32···O1^i	0.90	2.44	3.329 (2)	168
C30—H31···O1^i	0.98	2.48	3.307 (3)	142
C24—H24···O2^ii	0.96	2.69	3.544 (2)	148

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