1-{(2E)-2-[(Aminocarbonothioyl)hydrazono]-2-(3-mesityl-3-methylcyclobutyl)ethyl}pyrrolidine-2,5-dione

The molecule of the title compound, C₂₁H₂₈N₄O₂S, contains three rings, namely cyclo­butane, pyrrolidine and benzene. In the wedge-shaped cyclo­butane ring, the maximum deviation from planarity is 0.151 (3) Å. The mol­ecules are linked by N—H...S and N—H...O intermolecular hydrogen bonds.

Key indicators

• Single-crystal X-ray study
• T = 293 K
• Mean [sigma](C-C) = 0.005 Å
• R factor = 0.043
• wR factor = 0.110
• Data-to-parameter ratio = 14.6

checkCIF/PLATON results

No syntax errors found



Alert level C
PLAT031_ALERT_4_C Refined Extinction Parameter within Range ......       2.91 Sigma
PLAT241_ALERT_2_C Check High   U(eq) as Compared to Neighbors ....         C6
PLAT242_ALERT_2_C Check Low    U(eq) as Compared to Neighbors ....         C4
PLAT340_ALERT_3_C Low Bond Precision on C-C bonds (x 1000) Ang ...          5
PLAT412_ALERT_2_C Short Intra XH3 .. XHn     H9B    ..  H21C     =       1.89 Ang.
PLAT420_ALERT_2_C D-H Without Acceptor       N2     -   H2     ...          ?
PLAT790_ALERT_4_C Centre of Gravity not Within Unit Cell: Resd.  #          1
              C21 H28 N4 O2 S

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               3703
           Count of symmetry unique reflns         2132
           Completeness (_total/calc)            173.69%
           TEST3: Check Friedels for noncentro structure
           Estimate of Friedel pairs measured      1571
           Fraction of Friedel pairs measured     0.737
           Are heavy atom types Z>Si present          yes

   0 ALERT level A = In general: serious problem
   0 ALERT level B = Potentially serious problem
   7 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
   4 ALERT type 2 Indicator that the structure model may be wrong or deficient
   1 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, 2001); cell refinement: X-AREA; data reduction: X-RED (Stoe & Cie, 2001); 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, 1990); software used to prepare material for publication: WinGX (Farrugia, 1999).

1-{(2E)-2-[(Aminocarbonothioyl)hydrazono]-2-(3-mesityl-3- methylcyclobutyl)ethyl}pyrrolidine-2,5-dione

Crystal data

C21H28N4O2S	F(000) = 856
Mr = 400.53	Dx = 1.265 Mg m^−3
Orthorhombic, P212121	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2ac 2ab	Cell parameters from 4921 reflections
a = 8.8720 (7) Å	θ = 1.2–29.8°
b = 10.8100 (11) Å	µ = 0.18 mm^−1
c = 21.9284 (19) Å	T = 293 K
V = 2103.1 (3) Å^3	Shapeless, colourless
Z = 4	0.52 × 0.34 × 0.22 mm

Data collection

Stoe IPDS 2 diffractometer	3703 independent reflections
Radiation source: fine-focus sealed tube	2270 reflections with I > 2σ(I)
Plane graphite monochromator	Rint = 0.044
Detector resolution: 6.67 pixels mm^-1	θmax = 25.0°, θmin = 1.9°
φ scans	h = −10→9
Absorption correction: integration (X-RED; Stoe & Cie, 2001)	k = −12→11
Tmin = 0.936, Tmax = 0.971	l = −26→26
9857 measured reflections

Refinement

Refinement on F^2	Hydrogen site location: inferred from neighbouring sites
Least-squares matrix: full	H-atom parameters constrained
R[F^2 > 2σ(F^2)] = 0.043	w = 1/[σ^2(Fo^2) + (0.0586P)^2] where P = (Fo^2 + 2Fc^2)/3
wR(F^2) = 0.110	(Δ/σ)max < 0.001
S = 0.88	Δρmax = 0.20 e Å^−3
3703 reflections	Δρmin = −0.18 e Å^−3
254 parameters	Extinction correction: SHELXL97 (Sheldrick, 1997), Fc^* = kFc[1+0.001xFc^2λ^3/sin(2θ)]^-1/4
0 restraints	Extinction coefficient: 0.0032 (11)
Primary atom site location: structure-invariant direct methods	Absolute structure: Flack (1983), with x Friedel pairs
Secondary atom site location: difference Fourier map	Absolute structure parameter: 0.00 (13)

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	−0.0857 (4)	−0.0323 (4)	−0.14382 (14)	0.1229 (13)
C6	−0.1419 (5)	−0.2425 (6)	−0.1106 (2)	0.1157 (17)
H6A	−0.1455	−0.2825	−0.1502	0.139*
H6B	−0.2443	−0.2285	−0.0967	0.139*
C7	−0.0586 (5)	−0.1233 (5)	−0.11463 (18)	0.0875 (13)
C5	−0.0575 (5)	−0.3217 (5)	−0.0656 (2)	0.1064 (15)
H5A	−0.1221	−0.3454	−0.0319	0.128*
H5B	−0.0192	−0.3959	−0.0851	0.128*
C12	0.3184 (4)	−0.3655 (3)	−0.24173 (14)	0.0648 (9)
H12A	0.2297	−0.3146	−0.2419	0.097*
H12B	0.2911	−0.4491	−0.2319	0.097*
H12C	0.3648	−0.3633	−0.2813	0.097*
N4	0.0645 (3)	−0.1326 (3)	−0.07689 (12)	0.0667 (7)
C4	0.0674 (5)	−0.2423 (4)	−0.04439 (16)	0.0776 (10)
C3	0.1775 (4)	−0.0367 (3)	−0.06958 (17)	0.0726 (10)
H3A	0.2021	−0.0295	−0.0266	0.087*
H3B	0.1347	0.0415	−0.0825	0.087*
C8	0.3209 (4)	−0.1577 (3)	−0.15280 (13)	0.0522 (7)
H8	0.2261	−0.1537	−0.1756	0.063*
C11	0.4303 (4)	−0.3165 (2)	−0.19367 (12)	0.0482 (7)
C10	0.4504 (4)	−0.1721 (3)	−0.19732 (13)	0.0528 (8)
H10A	0.5463	−0.1429	−0.1817	0.063*
H10B	0.4301	−0.1378	−0.2374	0.063*
C9	0.3484 (4)	−0.2920 (3)	−0.13235 (14)	0.0568 (8)
H9A	0.2568	−0.3397	−0.1271	0.068*
H9B	0.4132	−0.2992	−0.0969	0.068*
O2	0.1597 (4)	−0.2667 (4)	−0.00665 (13)	0.1083 (10)
C1	0.3205 (4)	−0.0589 (3)	−0.10468 (13)	0.0528 (8)
C19	0.6713 (4)	−0.2810 (3)	−0.28727 (14)	0.0668 (9)
H19A	0.5768	−0.2384	−0.2836	0.100*
H19B	0.6763	−0.3211	−0.3263	0.100*
H19C	0.7525	−0.2228	−0.2837	0.100*
C13	0.5705 (4)	−0.3973 (2)	−0.19327 (12)	0.0487 (7)
C14	0.6841 (4)	−0.3768 (3)	−0.23728 (13)	0.0534 (8)
C21	0.4668 (5)	−0.5378 (3)	−0.10842 (16)	0.0769 (11)
H21A	0.5036	−0.6056	−0.0844	0.115*
H21B	0.3798	−0.5639	−0.1311	0.115*
H21C	0.4396	−0.4705	−0.0820	0.115*
N1	0.4429 (3)	0.0007 (2)	−0.09478 (10)	0.0573 (7)
C18	0.5886 (4)	−0.4957 (3)	−0.15214 (13)	0.0552 (8)
N2	0.4392 (4)	0.0900 (2)	−0.04881 (11)	0.0620 (7)
H2	0.3548	0.1115	−0.0326	0.074*
C15	0.8135 (4)	−0.4490 (3)	−0.23612 (16)	0.0651 (9)
H15	0.8872	−0.4350	−0.2655	0.078*
C17	0.7229 (4)	−0.5630 (3)	−0.15342 (16)	0.0684 (10)
H17	0.7353	−0.6268	−0.1254	0.082*
C16	0.8375 (4)	−0.5399 (3)	−0.19378 (17)	0.0692 (9)
C2	0.5686 (5)	0.1421 (3)	−0.03012 (14)	0.0603 (8)
S1	0.56572 (12)	0.24478 (10)	0.02692 (4)	0.0801 (3)
N3	0.6932 (4)	0.1101 (3)	−0.05877 (15)	0.0839 (10)
H3C	0.6895	0.0576	−0.0882	0.101*
H3D	0.7781	0.1416	−0.0480	0.101*
C20	0.9799 (4)	−0.6164 (4)	−0.1929 (2)	0.0994 (14)
H20A	1.0471	−0.5877	−0.2241	0.149*
H20B	0.9553	−0.7016	−0.2001	0.149*
H20C	1.0278	−0.6086	−0.1538	0.149*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
O1	0.095 (2)	0.176 (4)	0.098 (2)	0.049 (3)	0.0027 (19)	0.008 (2)
C6	0.076 (3)	0.177 (5)	0.094 (3)	−0.053 (4)	0.004 (2)	−0.032 (4)
C7	0.057 (3)	0.139 (4)	0.066 (2)	0.009 (3)	0.004 (2)	−0.022 (2)
C5	0.078 (3)	0.117 (4)	0.125 (3)	−0.038 (3)	0.026 (3)	−0.034 (3)
C12	0.053 (2)	0.063 (2)	0.079 (2)	−0.0024 (19)	−0.0095 (18)	−0.0176 (17)
N4	0.0505 (17)	0.075 (2)	0.0745 (16)	−0.0022 (17)	0.0008 (17)	−0.0230 (16)
C4	0.070 (2)	0.093 (3)	0.070 (2)	−0.018 (3)	0.013 (2)	−0.021 (2)
C3	0.064 (2)	0.059 (2)	0.096 (2)	0.001 (2)	0.006 (2)	−0.0231 (19)
C8	0.0505 (19)	0.0425 (16)	0.0635 (18)	0.0019 (16)	−0.0054 (16)	−0.0099 (14)
C11	0.0472 (18)	0.0387 (15)	0.0585 (16)	−0.0009 (15)	−0.0004 (17)	−0.0053 (13)
C10	0.054 (2)	0.0433 (17)	0.0615 (17)	−0.0015 (16)	−0.0068 (16)	−0.0038 (13)
C9	0.053 (2)	0.0474 (19)	0.0697 (19)	−0.0040 (15)	0.0065 (16)	−0.0039 (14)
O2	0.111 (2)	0.125 (3)	0.0882 (17)	−0.001 (2)	−0.0120 (18)	0.0003 (18)
C1	0.054 (2)	0.0423 (16)	0.0618 (17)	0.0061 (17)	−0.0028 (16)	−0.0053 (14)
C19	0.065 (2)	0.060 (2)	0.076 (2)	−0.0057 (19)	0.0168 (17)	0.0013 (17)
C13	0.0480 (17)	0.0428 (16)	0.0552 (15)	0.0006 (15)	−0.0043 (17)	−0.0098 (13)
C14	0.0481 (19)	0.0476 (17)	0.0644 (18)	−0.0047 (17)	−0.0007 (16)	−0.0082 (15)
C21	0.104 (3)	0.049 (2)	0.078 (2)	0.010 (2)	0.014 (2)	0.0132 (17)
N1	0.0610 (18)	0.0413 (14)	0.0695 (16)	−0.0003 (15)	−0.0052 (14)	−0.0104 (12)
C18	0.063 (2)	0.0431 (17)	0.0597 (17)	0.0051 (18)	0.0007 (16)	−0.0029 (14)
N2	0.0602 (17)	0.0537 (16)	0.0721 (16)	−0.0063 (15)	−0.0015 (15)	−0.0188 (13)
C15	0.054 (2)	0.064 (2)	0.077 (2)	0.002 (2)	0.0056 (18)	−0.0120 (18)
C17	0.081 (3)	0.053 (2)	0.071 (2)	0.012 (2)	−0.0129 (19)	0.0017 (17)
C16	0.054 (2)	0.070 (2)	0.083 (2)	0.010 (2)	−0.010 (2)	−0.014 (2)
C2	0.071 (2)	0.0446 (17)	0.0652 (17)	−0.0022 (19)	−0.007 (2)	−0.0035 (15)
S1	0.0854 (7)	0.0730 (6)	0.0819 (5)	−0.0114 (6)	−0.0063 (5)	−0.0265 (5)
N3	0.062 (2)	0.083 (2)	0.107 (2)	−0.0051 (18)	−0.0055 (19)	−0.0308 (18)
C20	0.068 (3)	0.109 (3)	0.121 (3)	0.034 (2)	−0.015 (2)	−0.016 (3)

Geometric parameters (Å, º)

O1—C7	1.198 (5)	C9—H9B	0.9700
C6—C7	1.488 (7)	C1—N1	1.281 (4)
C6—C5	1.505 (7)	C19—C14	1.512 (4)
C6—H6A	0.9700	C19—H19A	0.9600
C6—H6B	0.9700	C19—H19B	0.9600
C7—N4	1.374 (5)	C19—H19C	0.9600
C5—C4	1.477 (6)	C13—C18	1.404 (4)
C5—H5A	0.9700	C13—C14	1.413 (4)
C5—H5B	0.9700	C14—C15	1.388 (5)
C12—C11	1.542 (4)	C21—C18	1.514 (5)
C12—H12A	0.9600	C21—H21A	0.9600
C12—H12B	0.9600	C21—H21B	0.9600
C12—H12C	0.9600	C21—H21C	0.9600
N4—C4	1.384 (5)	N1—N2	1.396 (3)
N4—C3	1.451 (4)	C18—C17	1.397 (5)
C4—O2	1.194 (5)	N2—C2	1.343 (4)
C3—C1	1.503 (5)	N2—H2	0.8600
C3—H3A	0.9700	C15—C16	1.368 (5)
C3—H3B	0.9700	C15—H15	0.9300
C8—C1	1.501 (4)	C17—C16	1.371 (5)
C8—C10	1.515 (4)	C17—H17	0.9300
C8—C9	1.539 (4)	C16—C20	1.510 (5)
C8—H8	0.9800	C2—N3	1.317 (5)
C11—C13	1.520 (4)	C2—S1	1.672 (3)
C11—C9	1.551 (4)	N3—H3C	0.8600
C11—C10	1.573 (4)	N3—H3D	0.8600
C10—H10A	0.9700	C20—H20A	0.9600
C10—H10B	0.9700	C20—H20B	0.9600
C9—H9A	0.9700	C20—H20C	0.9600
C7—C6—C5	106.5 (4)	C11—C9—H9A	113.8
C7—C6—H6A	110.4	C8—C9—H9B	113.8
C5—C6—H6A	110.4	C11—C9—H9B	113.8
C7—C6—H6B	110.4	H9A—C9—H9B	111.0
C5—C6—H6B	110.4	N1—C1—C8	118.4 (3)
H6A—C6—H6B	108.6	N1—C1—C3	123.3 (3)
O1—C7—N4	122.8 (5)	C8—C1—C3	118.4 (3)
O1—C7—C6	130.0 (5)	C14—C19—H19A	109.5
N4—C7—C6	107.2 (4)	C14—C19—H19B	109.5
C4—C5—C6	104.4 (4)	H19A—C19—H19B	109.5
C4—C5—H5A	110.9	C14—C19—H19C	109.5
C6—C5—H5A	110.9	H19A—C19—H19C	109.5
C4—C5—H5B	110.9	H19B—C19—H19C	109.5
C6—C5—H5B	110.9	C18—C13—C14	118.4 (3)
H5A—C5—H5B	108.9	C18—C13—C11	122.2 (3)
C11—C12—H12A	109.5	C14—C13—C11	119.3 (3)
C11—C12—H12B	109.5	C15—C14—C13	119.3 (3)
H12A—C12—H12B	109.5	C15—C14—C19	117.4 (3)
C11—C12—H12C	109.5	C13—C14—C19	123.3 (3)
H12A—C12—H12C	109.5	C18—C21—H21A	109.5
H12B—C12—H12C	109.5	C18—C21—H21B	109.5
C7—N4—C4	112.8 (4)	H21A—C21—H21B	109.5
C7—N4—C3	124.3 (4)	C18—C21—H21C	109.5
C4—N4—C3	122.8 (3)	H21A—C21—H21C	109.5
O2—C4—N4	124.0 (4)	H21B—C21—H21C	109.5
O2—C4—C5	127.2 (5)	C1—N1—N2	116.7 (3)
N4—C4—C5	108.8 (4)	C17—C18—C13	118.6 (3)
N4—C3—C1	114.4 (3)	C17—C18—C21	117.8 (3)
N4—C3—H3A	108.7	C13—C18—C21	123.5 (3)
C1—C3—H3A	108.7	C2—N2—N1	119.3 (3)
N4—C3—H3B	108.7	C2—N2—H2	120.3
C1—C3—H3B	108.7	N1—N2—H2	120.3
H3A—C3—H3B	107.6	C16—C15—C14	123.0 (3)
C1—C8—C10	121.8 (3)	C16—C15—H15	118.5
C1—C8—C9	117.8 (2)	C14—C15—H15	118.5
C10—C8—C9	88.3 (2)	C16—C17—C18	123.4 (3)
C1—C8—H8	109.0	C16—C17—H17	118.3
C10—C8—H8	109.0	C18—C17—H17	118.3
C9—C8—H8	109.0	C15—C16—C17	116.9 (3)
C13—C11—C12	109.4 (2)	C15—C16—C20	122.2 (4)
C13—C11—C9	118.4 (2)	C17—C16—C20	120.8 (4)
C12—C11—C9	110.5 (3)	N3—C2—N2	117.5 (3)
C13—C11—C10	118.5 (3)	N3—C2—S1	123.0 (3)
C12—C11—C10	112.3 (3)	N2—C2—S1	119.5 (3)
C9—C11—C10	85.9 (2)	C2—N3—H3C	120.0
C8—C10—C11	89.0 (2)	C2—N3—H3D	120.0
C8—C10—H10A	113.8	H3C—N3—H3D	120.0
C11—C10—H10A	113.8	C16—C20—H20A	109.5
C8—C10—H10B	113.8	C16—C20—H20B	109.5
C11—C10—H10B	113.8	H20A—C20—H20B	109.5
H10A—C10—H10B	111.0	C16—C20—H20C	109.5
C8—C9—C11	89.0 (2)	H20A—C20—H20C	109.5
C8—C9—H9A	113.8	H20B—C20—H20C	109.5

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
N3—H3D···S1^i	0.86	2.87	3.725 (3)	173
N3—H3C···O1^ii	0.86	2.53	3.114 (5)	126

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