1-Methyl-1-phenyl-3-(phthalimido­acetyl)­cyclo­butane

The title mol­ecule, C₂₁H₁₉NO₃, consists of three essentially planar fragments. There is negligible puckering in the cyclo­butane ring. The crystal structure is stabilized not only by weak intermolecular C—H...O hydrogen-bond interactions but also by weak C—H...π(ring) interactions, with an H...Cg distance of 2.85 Å (where Cg is the centroid of the phthalimido six-membered ring).

Key indicators

• Single-crystal X-ray study
• T = 293 K
• Mean [sigma](C-C) = 0.004 Å
• R factor = 0.032
• wR factor = 0.067
• Data-to-parameter ratio = 7.1

checkCIF/PLATON results

No syntax errors found



Alert level C
RINTA01_ALERT_3_C  The value of Rint is greater than 0.10
            Rint given   0.122
PLAT020_ALERT_3_C The value of Rint is greater than 0.10 .........       0.12
PLAT063_ALERT_3_C Crystal Probably too Large for Beam Size .......       0.80 mm
PLAT089_ALERT_3_C Poor Data / Parameter Ratio (Zmax .LT. 18) .....       7.10
PLAT128_ALERT_4_C Non-standard setting of Space group Pna21   ....    P21nb
PLAT230_ALERT_2_C Hirshfeld Test Diff for    C3     -   C15      =       5.74 su
PLAT241_ALERT_2_C Check High   U(eq) as Compared to Neighbors ....         C4
PLAT242_ALERT_2_C Check Low    U(eq) as Compared to Neighbors ....         C3
PLAT480_ALERT_4_C Long H...A H-Bond Reported H17    ..  CG3      =       2.85 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           25.00
           From the CIF: _reflns_number_total               1611
           Count of symmetry unique reflns         1611
           Completeness (_total/calc)            100.00%
           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

   0 ALERT level A = In general: serious problem
   0 ALERT level B = Potentially serious problem
   9 ALERT level C = Check and explain
   1 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
   4 ALERT type 3 Indicator that the structure quality may be low
   3 ALERT type 4 Improvement, methodology, query or suggestion

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Computing details

Data collection: X-AREA (Stoe & Cie, 2002); cell refinement: X-AREA; data reduction: X-RED (Stoe & Cie, 2002); program(s) used to solve structure: SHELXS86 (Sheldrick, 1990); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997) and PLATON (Spek, 1997); software used to prepare material for publication: WinGX (Farrugia, 1999).

1-Methyl-1-phenyl-3-(phthalimidoacetyl)cyclobutane

Crystal data

C21H19NO3	F(000) = 704
Mr = 333.37	Dx = 1.291 Mg m^−3
Orthorhombic, P21nb	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P -2bc 2a	Cell parameters from 11804 reflections
a = 9.1755 (9) Å	θ = 2.1–29.6°
b = 9.4488 (7) Å	µ = 0.09 mm^−1
c = 19.7807 (18) Å	T = 293 K
V = 1714.9 (3) Å^3	Plate, colourless
Z = 4	0.80 × 0.38 × 0.06 mm

Data collection

STOE IPDS 2 diffractometer	1611 independent reflections
Radiation source: sealed X-ray tube	1229 reflections with I > 2σ(I)
Plane graphite monochromator	Rint = 0.122
Detector resolution: 6.67 pixels mm^-1	θmax = 25.0°, θmin = 2.1°
rotation method scans	h = −10→10
Absorption correction: integration STOE X-RED (Stoe & Cie, 2002)	k = −10→11
Tmin = 0.952, Tmax = 0.993	l = −23→23
21176 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)] = 0.033	H-atom parameters constrained
wR(F^2) = 0.067	w = 1/[σ^2(Fo^2) + (0.0291P)^2] where P = (Fo^2 + 2Fc^2)/3
S = 1.01	(Δ/σ)max = 0.036
1611 reflections	Δρmax = 0.11 e Å^−3
227 parameters	Δρmin = −0.12 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: 0.031 (2)

Special details

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.

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

	x	y	z	Uiso*/Ueq
O1	−0.0822 (2)	0.8443 (2)	0.27477 (10)	0.0789 (6)
O2	0.13871 (19)	0.4419 (2)	0.34655 (9)	0.0648 (5)
O3	0.3239 (2)	0.7473 (2)	0.30420 (10)	0.0836 (7)
N1	0.0457 (2)	0.6397 (2)	0.29553 (10)	0.0545 (5)
C1	0.4087 (3)	0.6206 (3)	0.20751 (13)	0.0586 (7)
H1	0.4033	0.5172	0.2043	0.070*
C2	0.4050 (3)	0.6890 (3)	0.13614 (12)	0.0592 (7)
H2A	0.3951	0.6208	0.0997	0.071*
H2B	0.3335	0.7641	0.1318	0.071*
C3	0.5629 (3)	0.7434 (3)	0.14602 (11)	0.0533 (6)
C4	0.5671 (3)	0.6693 (4)	0.21632 (13)	0.0747 (9)
H4A	0.6363	0.5919	0.2188	0.090*
H4B	0.5808	0.7343	0.2537	0.090*
C5	0.0524 (3)	0.5382 (3)	0.34549 (12)	0.0498 (6)
C6	−0.0602 (2)	0.5761 (3)	0.39567 (11)	0.0475 (6)
C7	−0.1009 (3)	0.5098 (3)	0.45435 (11)	0.0565 (6)
H7	−0.0577	0.4256	0.4681	0.068*
C8	−0.2094 (3)	0.5739 (3)	0.49215 (13)	0.0654 (7)
H8	−0.2397	0.5321	0.5323	0.078*
C9	−0.2728 (3)	0.6976 (3)	0.47151 (15)	0.0701 (8)
H9	−0.3449	0.7382	0.4983	0.084*
C10	−0.2330 (3)	0.7637 (3)	0.41214 (16)	0.0677 (8)
H10	−0.2769	0.8475	0.3981	0.081*
C11	−0.1249 (3)	0.6994 (3)	0.37452 (12)	0.0519 (6)
C12	−0.0573 (3)	0.7428 (3)	0.30956 (13)	0.0551 (6)
C13	0.1425 (3)	0.6381 (3)	0.23795 (12)	0.0604 (7)
H13A	0.1067	0.7046	0.2045	0.073*
H13B	0.1409	0.5445	0.2178	0.073*
C14	0.2975 (3)	0.6758 (3)	0.25558 (12)	0.0571 (7)
C15	0.5694 (4)	0.9021 (4)	0.15099 (18)	0.0926 (11)
H15A	0.4990	0.9343	0.1834	0.139*
H15B	0.5482	0.9428	0.1076	0.139*
H15C	0.6652	0.9304	0.1651	0.139*
C16	0.6729 (2)	0.6926 (3)	0.09518 (12)	0.0506 (6)
C17	0.6405 (3)	0.6943 (3)	0.02669 (12)	0.0627 (7)
H17	0.5479	0.7215	0.0127	0.075*
C18	0.7425 (4)	0.6565 (4)	−0.02107 (14)	0.0776 (9)
H18	0.7187	0.6592	−0.0668	0.093*
C19	0.8792 (3)	0.6149 (3)	−0.00125 (17)	0.0775 (9)
H19	0.9483	0.5888	−0.0333	0.093*
C20	0.9130 (3)	0.6121 (3)	0.06599 (17)	0.0778 (8)
H20	1.0052	0.5832	0.0798	0.093*
C21	0.8113 (3)	0.6516 (3)	0.11330 (14)	0.0673 (8)
H21	0.8368	0.6507	0.1588	0.081*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
O1	0.0758 (13)	0.0775 (13)	0.0835 (13)	0.0121 (12)	0.0138 (11)	0.0252 (11)
O2	0.0585 (10)	0.0754 (13)	0.0606 (11)	0.0183 (11)	0.0000 (9)	−0.0036 (9)
O3	0.0721 (14)	0.1144 (17)	0.0644 (13)	−0.0196 (12)	0.0105 (11)	−0.0259 (12)
N1	0.0475 (12)	0.0677 (13)	0.0484 (11)	0.0056 (11)	0.0101 (10)	0.0027 (11)
C1	0.0486 (15)	0.0711 (16)	0.0561 (14)	0.0037 (13)	0.0092 (13)	0.0084 (12)
C2	0.0474 (14)	0.0853 (18)	0.0450 (13)	0.0030 (13)	0.0032 (11)	0.0022 (12)
C3	0.0512 (14)	0.0669 (17)	0.0417 (13)	0.0011 (13)	0.0072 (11)	−0.0001 (12)
C4	0.0484 (15)	0.125 (3)	0.0507 (15)	−0.0013 (16)	0.0031 (13)	0.0209 (16)
C5	0.0437 (13)	0.0592 (16)	0.0465 (13)	0.0034 (13)	−0.0024 (11)	−0.0052 (12)
C6	0.0422 (12)	0.0550 (15)	0.0453 (12)	−0.0036 (12)	0.0027 (11)	−0.0055 (11)
C7	0.0555 (15)	0.0637 (15)	0.0504 (14)	−0.0022 (14)	−0.0008 (13)	0.0005 (12)
C8	0.0595 (16)	0.084 (2)	0.0530 (15)	−0.0111 (17)	0.0138 (14)	−0.0057 (14)
C9	0.0560 (16)	0.081 (2)	0.0731 (19)	−0.0016 (17)	0.0237 (15)	−0.0143 (17)
C10	0.0546 (16)	0.0657 (18)	0.0828 (19)	0.0090 (14)	0.0141 (14)	−0.0030 (15)
C11	0.0444 (13)	0.0554 (15)	0.0561 (14)	−0.0012 (12)	0.0047 (11)	−0.0018 (12)
C12	0.0505 (15)	0.0555 (15)	0.0595 (15)	0.0008 (13)	0.0044 (12)	0.0052 (13)
C13	0.0501 (14)	0.0849 (19)	0.0464 (14)	−0.0044 (14)	0.0119 (13)	−0.0012 (13)
C14	0.0532 (15)	0.0689 (18)	0.0492 (14)	−0.0048 (14)	0.0072 (12)	0.0057 (14)
C15	0.104 (3)	0.086 (2)	0.088 (2)	−0.001 (2)	0.031 (2)	−0.0243 (18)
C16	0.0479 (14)	0.0538 (15)	0.0501 (14)	−0.0026 (11)	0.0102 (11)	0.0004 (12)
C17	0.0575 (16)	0.0797 (19)	0.0510 (15)	0.0029 (16)	0.0063 (14)	−0.0043 (13)
C18	0.072 (2)	0.102 (2)	0.0588 (17)	−0.0123 (18)	0.0165 (16)	−0.0200 (16)
C19	0.0591 (19)	0.085 (2)	0.088 (2)	−0.0115 (15)	0.0307 (18)	−0.0305 (17)
C20	0.0534 (16)	0.085 (2)	0.095 (2)	0.0042 (16)	0.0102 (17)	−0.0033 (17)
C21	0.0496 (15)	0.086 (2)	0.0662 (16)	−0.0025 (15)	0.0058 (14)	0.0015 (14)

Geometric parameters (Å, º)

O1—C12	1.203 (3)	C8—H8	0.9300
O2—C5	1.206 (3)	C9—C10	1.380 (4)
O3—C14	1.201 (3)	C9—H9	0.9300
N1—C5	1.378 (3)	C10—C11	1.381 (3)
N1—C12	1.385 (3)	C10—H10	0.9300
N1—C13	1.444 (3)	C11—C12	1.484 (3)
C1—C14	1.489 (4)	C13—C14	1.507 (4)
C1—C4	1.534 (4)	C13—H13A	0.9700
C1—C2	1.553 (3)	C13—H13B	0.9700
C1—H1	0.9800	C15—H15A	0.9600
C2—C3	1.550 (4)	C15—H15B	0.9600
C2—H2A	0.9700	C15—H15C	0.9599
C2—H2B	0.9700	C16—C21	1.375 (4)
C3—C15	1.504 (4)	C16—C17	1.387 (3)
C3—C16	1.503 (3)	C17—C18	1.376 (4)
C3—C4	1.557 (4)	C17—H17	0.9301
C4—H4A	0.9700	C18—C19	1.372 (5)
C4—H4B	0.9700	C18—H18	0.9300
C5—C6	1.477 (3)	C19—C20	1.366 (4)
C6—C11	1.373 (3)	C19—H19	0.9300
C6—C7	1.371 (3)	C20—C21	1.373 (4)
C7—C8	1.385 (3)	C20—H20	0.9299
C7—H7	0.9300	C21—H21	0.9300
C8—C9	1.368 (4)
C5—N1—C12	112.1 (2)	C11—C10—C9	116.7 (3)
C5—N1—C13	122.1 (2)	C11—C10—H10	121.6
C12—N1—C13	125.8 (2)	C9—C10—H10	121.6
C14—C1—C4	118.1 (2)	C6—C11—C10	121.3 (2)
C14—C1—C2	114.8 (2)	C6—C11—C12	108.5 (2)
C4—C1—C2	89.97 (19)	C10—C11—C12	130.2 (3)
C14—C1—H1	110.8	O1—C12—N1	125.2 (2)
C4—C1—H1	110.8	O1—C12—C11	129.5 (2)
C2—C1—H1	110.8	N1—C12—C11	105.3 (2)
C3—C2—C1	90.15 (19)	N1—C13—C14	113.3 (2)
C3—C2—H2A	113.6	N1—C13—H13A	108.9
C1—C2—H2A	113.6	C14—C13—H13A	108.9
C3—C2—H2B	113.6	N1—C13—H13B	108.9
C1—C2—H2B	113.6	C14—C13—H13B	108.9
H2A—C2—H2B	110.9	H13A—C13—H13B	107.7
C15—C3—C16	109.6 (2)	O3—C14—C1	124.8 (2)
C15—C3—C2	112.1 (2)	O3—C14—C13	120.6 (2)
C16—C3—C2	115.9 (2)	C1—C14—C13	114.6 (2)
C15—C3—C4	112.9 (2)	C3—C15—H15A	109.5
C16—C3—C4	115.9 (2)	C3—C15—H15B	109.5
C2—C3—C4	89.22 (19)	H15A—C15—H15B	109.5
C1—C4—C3	90.59 (19)	C3—C15—H15C	109.5
C1—C4—H4A	113.5	H15A—C15—H15C	109.5
C3—C4—H4A	113.5	H15B—C15—H15C	109.5
C1—C4—H4B	113.5	C21—C16—C17	117.1 (2)
C3—C4—H4B	113.5	C21—C16—C3	122.4 (2)
H4A—C4—H4B	110.8	C17—C16—C3	120.4 (2)
O2—C5—N1	124.5 (2)	C18—C17—C16	121.5 (3)
O2—C5—C6	129.1 (2)	C18—C17—H17	119.3
N1—C5—C6	106.4 (2)	C16—C17—H17	119.3
C11—C6—C7	121.9 (2)	C19—C18—C17	120.0 (3)
C11—C6—C5	107.7 (2)	C19—C18—H18	120.0
C7—C6—C5	130.4 (2)	C17—C18—H18	120.0
C6—C7—C8	116.9 (2)	C20—C19—C18	119.4 (3)
C6—C7—H7	121.5	C20—C19—H19	120.3
C8—C7—H7	121.5	C18—C19—H19	120.3
C9—C8—C7	121.2 (2)	C19—C20—C21	120.3 (3)
C9—C8—H8	119.4	C19—C20—H20	119.9
C7—C8—H8	119.4	C21—C20—H20	119.9
C8—C9—C10	121.9 (2)	C20—C21—C16	121.8 (3)
C8—C9—H9	119.0	C20—C21—H21	119.1
C10—C9—H9	119.0	C16—C21—H21	119.1
C14—C1—C2—C3	119.2 (2)	C13—N1—C12—O1	1.5 (4)
C4—C1—C2—C3	−2.1 (2)	C5—N1—C12—C11	−1.4 (3)
C1—C2—C3—C15	−112.4 (2)	C13—N1—C12—C11	−178.3 (2)
C1—C2—C3—C16	120.7 (2)	C6—C11—C12—O1	−179.6 (3)
C1—C2—C3—C4	2.0 (2)	C10—C11—C12—O1	−0.3 (5)
C14—C1—C4—C3	−116.3 (2)	C6—C11—C12—N1	0.2 (3)
C2—C1—C4—C3	2.1 (2)	C10—C11—C12—N1	179.6 (3)
C15—C3—C4—C1	111.7 (3)	C5—N1—C13—C14	−71.0 (3)
C16—C3—C4—C1	−120.7 (2)	C12—N1—C13—C14	105.6 (3)
C2—C3—C4—C1	−2.1 (2)	C4—C1—C14—O3	−6.1 (4)
C12—N1—C5—O2	−175.9 (2)	C2—C1—C14—O3	−110.3 (3)
C13—N1—C5—O2	1.1 (4)	C4—C1—C14—C13	172.4 (3)
C12—N1—C5—C6	2.0 (3)	C2—C1—C14—C13	68.1 (3)
C13—N1—C5—C6	179.0 (2)	N1—C13—C14—O3	−25.3 (4)
O2—C5—C6—C11	176.0 (2)	N1—C13—C14—C1	156.1 (2)
N1—C5—C6—C11	−1.8 (3)	C15—C3—C16—C21	93.4 (3)
O2—C5—C6—C7	−3.4 (4)	C2—C3—C16—C21	−138.5 (3)
N1—C5—C6—C7	178.8 (2)	C4—C3—C16—C21	−35.8 (4)
C11—C6—C7—C8	−0.9 (3)	C15—C3—C16—C17	−82.3 (3)
C5—C6—C7—C8	178.4 (2)	C2—C3—C16—C17	45.8 (4)
C6—C7—C8—C9	0.2 (4)	C4—C3—C16—C17	148.5 (3)
C7—C8—C9—C10	0.5 (4)	C21—C16—C17—C18	0.0 (4)
C8—C9—C10—C11	−0.4 (4)	C3—C16—C17—C18	176.0 (3)
C7—C6—C11—C10	1.0 (4)	C16—C17—C18—C19	0.6 (5)
C5—C6—C11—C10	−178.5 (2)	C17—C18—C19—C20	−0.3 (5)
C7—C6—C11—C12	−179.6 (2)	C18—C19—C20—C21	−0.5 (5)
C5—C6—C11—C12	0.9 (3)	C19—C20—C21—C16	1.2 (5)
C9—C10—C11—C6	−0.3 (4)	C17—C16—C21—C20	−0.9 (4)
C9—C10—C11—C12	−179.6 (3)	C3—C16—C21—C20	−176.7 (3)
C5—N1—C12—O1	178.4 (3)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
C13—H13A···O2^i	0.97	2.48	3.322 (3)	146
C2—H2B···O2^i	0.97	2.49	3.435 (3)	164
C17—H17···Cg3^ii	0.93	2.85	3.730 (3)	158

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