3′-(2-Chloro­phenyl)-1′-methyl-4′nitro­spiro­[indan-2,2′-pyrrolidine]-1,3-dione

In the title compound, C₁₉H₁₅ClN₂O₄, the pyrrolidine ring adopts an envelope conformation. The five-membered ring in the indanedione moiety also adopts an envelope conformation. The dihedral angle between the chloro­phenyl ring and the benzene ring of the indanedione moiety is 38.2 (1)°. The molecular structure is stabilized by intramolecular C—H...Cl and C—H...O interactions and the packing is stabilized by intermolecular C—H...O interactions.

Key indicators

• Single-crystal X-ray study
• T = 293 K
• Mean [sigma](C-C) = 0.004 Å
• R factor = 0.041
• wR factor = 0.102
• Data-to-parameter ratio = 13.6

checkCIF/PLATON results

No syntax errors found



Alert level A
PLAT029_ALERT_3_A _diffrn_measured_fraction_theta_full Low .......       0.47

Alert level C
PLAT094_ALERT_2_C Ratio of Maximum / Minimum Residual Density ....       2.35
PLAT241_ALERT_2_C Check High   U(eq) as Compared to Neighbors  for         C5
PLAT242_ALERT_2_C Check Low    U(eq) as Compared to Neighbors  for        N23
PLAT790_ALERT_4_C Centre of Gravity not Within Unit Cell: Resd.  #          1
              C19 H15 Cl N2 O4

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           27.93
           From the CIF: _reflns_number_total               3199
           Count of symmetry unique reflns         2111
           Completeness (_total/calc)            151.54%
           TEST3: Check Friedels for noncentro structure
           Estimate of Friedel pairs measured      1088
           Fraction of Friedel pairs measured     0.515
           Are heavy atom types Z>Si present          yes

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

---

Computing details

Data collection: SMART (Bruker, 2001); cell refinement: SAINT (Bruker, 2001); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEP-3 (Farrugia, 1997) and PLATON (Spek, 2003); software used to prepare material for publication: SHELXL97 and PARST (Nardelli, 1995).

3'-(2-Chlorophenyl)-1'-methyl-4'nitrospiro[indan-2, 2'-pyrrolidine]-1,3-dione

Crystal data

C19H15ClN2O4	F(000) = 768
Mr = 370.78	Dx = 1.408 Mg m^−3
Monoclinic, Cc	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: C -2yc	Cell parameters from 2598 reflections
a = 13.0966 (12) Å	θ = 2.6–26.1°
b = 8.6225 (8) Å	µ = 0.25 mm^−1
c = 15.7306 (14) Å	T = 293 K
β = 100.045 (1)°	Block, colourless
V = 1749.2 (3) Å^3	0.24 × 0.20 × 0.16 mm
Z = 4

Data collection

CCD Area Detector diffractometer	3013 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	Rint = 0.015
Graphite monochromator	θmax = 27.9°, θmin = 2.6°
ω scans	h = −16→16
5115 measured reflections	k = −10→9
3199 independent reflections	l = −20→20

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)] = 0.041	H-atom parameters constrained
wR(F^2) = 0.102	w = 1/[σ^2(Fo^2) + (0.0607P)^2 + 0.5297P] where P = (Fo^2 + 2Fc^2)/3
S = 1.02	(Δ/σ)max < 0.001
3199 reflections	Δρmax = 0.31 e Å^−3
235 parameters	Δρmin = −0.13 e Å^−3
2 restraints	Absolute structure: Flack (1983)
Primary atom site location: structure-invariant direct methods	Absolute structure parameter: 0.04 (6)

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
Cl1	0.06235 (5)	0.05876 (9)	0.01226 (5)	0.0620 (2)
N1	−0.29499 (17)	0.1249 (3)	−0.13195 (13)	0.0516 (5)
C2	−0.22614 (17)	0.1521 (3)	−0.05093 (13)	0.0384 (5)
C3	−0.17189 (16)	−0.0080 (3)	−0.03372 (13)	0.0364 (4)
H3	−0.1193	−0.0163	−0.0708	0.044*
C4	−0.26015 (19)	−0.1196 (3)	−0.06839 (14)	0.0430 (5)
H4	−0.2946	−0.1527	−0.0209	0.052*
C5	−0.3361 (2)	−0.0303 (4)	−0.1336 (2)	0.0640 (8)
H5A	−0.3410	−0.0755	−0.1907	0.077*
H5B	−0.4045	−0.0303	−0.1178	0.077*
C6	−0.3701 (3)	0.2459 (4)	−0.1616 (2)	0.0758 (10)
H6A	−0.3358	0.3447	−0.1577	0.114*
H6B	−0.4228	0.2466	−0.1262	0.114*
H6C	−0.4012	0.2263	−0.2205	0.114*
C7	−0.14665 (18)	0.2815 (3)	−0.05749 (13)	0.0388 (5)
C8	−0.12996 (16)	0.3654 (3)	0.02558 (14)	0.0377 (5)
C9	−0.0550 (2)	0.4748 (3)	0.05534 (18)	0.0523 (6)
H9	−0.0084	0.5089	0.0210	0.063*
C10	−0.0519 (2)	0.5316 (4)	0.1376 (2)	0.0618 (7)
H10	−0.0028	0.6062	0.1588	0.074*
C11	−0.1201 (3)	0.4800 (4)	0.18910 (18)	0.0624 (7)
H11	−0.1150	0.5185	0.2449	0.075*
C12	−0.1955 (2)	0.3727 (3)	0.15919 (15)	0.0503 (6)
H12	−0.2417	0.3387	0.1938	0.060*
C13	−0.20059 (16)	0.3167 (3)	0.07612 (13)	0.0377 (5)
C14	−0.27226 (17)	0.2023 (3)	0.02823 (15)	0.0422 (5)
O15	−0.35173 (14)	0.1556 (3)	0.04656 (15)	0.0652 (5)
O16	−0.10533 (16)	0.3056 (2)	−0.11809 (11)	0.0578 (5)
C17	−0.11888 (18)	−0.0347 (3)	0.05881 (13)	0.0383 (5)
C18	−0.01440 (19)	−0.0033 (3)	0.08565 (15)	0.0459 (5)
C19	0.0324 (2)	−0.0193 (4)	0.17093 (18)	0.0618 (7)
H19	0.1026	0.0022	0.1873	0.074*
C20	−0.0240 (3)	−0.0663 (4)	0.23109 (18)	0.0685 (9)
H20	0.0078	−0.0771	0.2884	0.082*
C21	−0.1271 (3)	−0.0978 (4)	0.20753 (17)	0.0619 (7)
H21	−0.1658	−0.1289	0.2488	0.074*
C22	−0.1739 (2)	−0.0834 (3)	0.12188 (15)	0.0492 (6)
H22	−0.2439	−0.1069	0.1062	0.059*
N23	−0.22128 (19)	−0.2603 (3)	−0.10985 (14)	0.0562 (5)
O24	−0.1343 (2)	−0.2661 (4)	−0.1227 (3)	0.1133 (11)
O25	−0.2826 (2)	−0.3616 (3)	−0.1315 (2)	0.1006 (9)

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
Cl1	0.0424 (3)	0.0684 (5)	0.0752 (4)	−0.0042 (3)	0.0101 (3)	−0.0019 (3)
N1	0.0540 (12)	0.0432 (13)	0.0498 (11)	−0.0036 (10)	−0.0127 (9)	−0.0027 (9)
C2	0.0407 (11)	0.0328 (12)	0.0385 (10)	−0.0045 (9)	−0.0016 (8)	−0.0008 (8)
C3	0.0383 (11)	0.0350 (12)	0.0352 (9)	−0.0059 (9)	0.0043 (8)	−0.0027 (8)
C4	0.0494 (12)	0.0387 (14)	0.0405 (11)	−0.0098 (10)	0.0071 (9)	−0.0067 (9)
C5	0.0570 (16)	0.0495 (18)	0.0750 (18)	−0.0060 (13)	−0.0178 (14)	−0.0118 (13)
C6	0.077 (2)	0.056 (2)	0.0789 (19)	0.0088 (15)	−0.0299 (17)	0.0006 (15)
C7	0.0457 (11)	0.0330 (12)	0.0367 (10)	−0.0034 (9)	0.0047 (8)	0.0028 (8)
C8	0.0400 (11)	0.0306 (13)	0.0416 (10)	−0.0037 (9)	0.0043 (9)	−0.0008 (8)
C9	0.0503 (13)	0.0456 (15)	0.0614 (15)	−0.0143 (11)	0.0111 (11)	−0.0067 (11)
C10	0.0610 (17)	0.0501 (18)	0.0692 (17)	−0.0128 (13)	−0.0029 (14)	−0.0201 (13)
C11	0.076 (2)	0.0621 (19)	0.0462 (13)	0.0003 (15)	0.0021 (12)	−0.0191 (12)
C12	0.0588 (15)	0.0497 (17)	0.0446 (12)	0.0051 (12)	0.0155 (11)	−0.0039 (11)
C13	0.0381 (10)	0.0334 (12)	0.0416 (10)	0.0005 (9)	0.0072 (8)	−0.0007 (8)
C14	0.0364 (11)	0.0365 (13)	0.0535 (12)	−0.0029 (9)	0.0074 (9)	0.0006 (10)
O15	0.0449 (10)	0.0629 (13)	0.0926 (14)	−0.0163 (9)	0.0257 (10)	−0.0099 (10)
O16	0.0800 (13)	0.0533 (12)	0.0442 (8)	−0.0137 (10)	0.0219 (8)	0.0004 (8)
C17	0.0469 (12)	0.0278 (12)	0.0385 (10)	0.0023 (9)	0.0023 (9)	−0.0014 (8)
C18	0.0480 (13)	0.0375 (13)	0.0498 (12)	0.0050 (10)	0.0019 (10)	−0.0057 (10)
C19	0.0589 (16)	0.0576 (18)	0.0600 (15)	0.0106 (13)	−0.0145 (13)	−0.0145 (13)
C20	0.091 (2)	0.069 (2)	0.0378 (12)	0.0175 (16)	−0.0104 (13)	−0.0045 (12)
C21	0.085 (2)	0.0582 (18)	0.0435 (13)	0.0053 (15)	0.0141 (13)	0.0070 (12)
C22	0.0571 (14)	0.0460 (15)	0.0438 (12)	−0.0004 (11)	0.0073 (10)	0.0036 (10)
N23	0.0666 (15)	0.0406 (13)	0.0585 (12)	−0.0046 (11)	0.0030 (11)	−0.0109 (10)
O24	0.0864 (18)	0.090 (2)	0.170 (3)	−0.0053 (15)	0.0398 (19)	−0.070 (2)
O25	0.0984 (19)	0.0518 (15)	0.150 (3)	−0.0230 (14)	0.0166 (18)	−0.0432 (16)

Geometric parameters (Å, º)

Cl1—C18	1.742 (3)	C9—C10	1.377 (4)
N1—C5	1.441 (4)	C9—H9	0.9300
N1—C2	1.446 (3)	C10—C11	1.381 (5)
N1—C6	1.454 (4)	C10—H10	0.9300
C2—C7	1.542 (3)	C11—C12	1.375 (4)
C2—C14	1.538 (3)	C11—H11	0.9300
C2—C3	1.555 (3)	C12—C13	1.384 (3)
C3—C17	1.517 (3)	C12—H12	0.9300
C3—C4	1.530 (3)	C13—C14	1.475 (3)
C3—H3	0.9800	C14—O15	1.197 (3)
C4—N23	1.507 (3)	C17—C18	1.386 (3)
C4—C5	1.510 (4)	C17—C22	1.389 (3)
C4—H4	0.9800	C18—C19	1.381 (4)
C5—H5A	0.9700	C19—C20	1.360 (5)
C5—H5B	0.9700	C19—H19	0.9300
C6—H6A	0.9600	C20—C21	1.364 (5)
C6—H6B	0.9600	C20—H20	0.9300
C6—H6C	0.9600	C21—C22	1.385 (4)
C7—O16	1.194 (3)	C21—H21	0.9300
C7—C8	1.476 (3)	C22—H22	0.9300
C8—C9	1.383 (3)	N23—O24	1.192 (3)
C8—C13	1.386 (3)	N23—O25	1.195 (3)
C5—N1—C2	109.9 (2)	C10—C9—C8	117.6 (2)
C5—N1—C6	115.5 (2)	C10—C9—H9	121.2
C2—N1—C6	116.7 (2)	C8—C9—H9	121.2
N1—C2—C7	112.53 (18)	C9—C10—C11	121.4 (3)
N1—C2—C14	119.12 (19)	C9—C10—H10	119.3
C7—C2—C14	102.47 (17)	C11—C10—H10	119.3
N1—C2—C3	101.81 (18)	C12—C11—C10	121.0 (2)
C7—C2—C3	111.16 (18)	C12—C11—H11	119.5
C14—C2—C3	109.93 (17)	C10—C11—H11	119.5
C17—C3—C4	116.0 (2)	C11—C12—C13	118.1 (2)
C17—C3—C2	114.9 (2)	C11—C12—H12	120.9
C4—C3—C2	101.70 (17)	C13—C12—H12	120.9
C17—C3—H3	108.0	C12—C13—C8	120.6 (2)
C4—C3—H3	108.0	C12—C13—C14	129.6 (2)
C2—C3—H3	108.0	C8—C13—C14	109.81 (18)
N23—C4—C5	110.4 (2)	O15—C14—C13	127.2 (2)
N23—C4—C3	111.7 (2)	O15—C14—C2	125.5 (2)
C5—C4—C3	106.8 (2)	C13—C14—C2	107.27 (17)
N23—C4—H4	109.3	C18—C17—C22	116.7 (2)
C5—C4—H4	109.3	C18—C17—C3	121.7 (2)
C3—C4—H4	109.3	C22—C17—C3	121.6 (2)
N1—C5—C4	105.1 (2)	C19—C18—C17	121.6 (2)
N1—C5—H5A	110.7	C19—C18—Cl1	117.7 (2)
C4—C5—H5A	110.7	C17—C18—Cl1	120.74 (17)
N1—C5—H5B	110.7	C20—C19—C18	120.2 (3)
C4—C5—H5B	110.7	C20—C19—H19	119.9
H5A—C5—H5B	108.8	C18—C19—H19	119.9
N1—C6—H6A	109.5	C21—C20—C19	120.1 (2)
N1—C6—H6B	109.5	C21—C20—H20	119.9
H6A—C6—H6B	109.5	C19—C20—H20	119.9
N1—C6—H6C	109.5	C20—C21—C22	119.7 (3)
H6A—C6—H6C	109.5	C20—C21—H21	120.1
H6B—C6—H6C	109.5	C22—C21—H21	120.1
O16—C7—C8	127.1 (2)	C21—C22—C17	121.7 (2)
O16—C7—C2	125.8 (2)	C21—C22—H22	119.2
C8—C7—C2	107.03 (16)	C17—C22—H22	119.2
C9—C8—C13	121.2 (2)	O24—N23—O25	122.3 (3)
C9—C8—C7	128.4 (2)	O24—N23—C4	120.8 (2)
C13—C8—C7	110.40 (18)	O25—N23—C4	116.8 (2)
C5—N1—C2—C7	156.2 (2)	C11—C12—C13—C8	1.4 (4)
C6—N1—C2—C7	−69.7 (3)	C11—C12—C13—C14	179.8 (3)
C5—N1—C2—C14	−83.8 (3)	C9—C8—C13—C12	−2.3 (4)
C6—N1—C2—C14	50.2 (3)	C7—C8—C13—C12	176.0 (2)
C5—N1—C2—C3	37.2 (3)	C9—C8—C13—C14	179.0 (2)
C6—N1—C2—C3	171.2 (2)	C7—C8—C13—C14	−2.7 (3)
N1—C2—C3—C17	−162.18 (17)	C12—C13—C14—O15	14.4 (4)
C7—C2—C3—C17	77.8 (2)	C8—C13—C14—O15	−167.1 (3)
C14—C2—C3—C17	−35.0 (2)	C12—C13—C14—C2	−165.5 (2)
N1—C2—C3—C4	−36.1 (2)	C8—C13—C14—C2	13.0 (3)
C7—C2—C3—C4	−156.17 (16)	N1—C2—C14—O15	38.0 (4)
C14—C2—C3—C4	91.08 (19)	C7—C2—C14—O15	162.9 (2)
C17—C3—C4—N23	−89.9 (2)	C3—C2—C14—O15	−78.8 (3)
C2—C3—C4—N23	144.74 (18)	N1—C2—C14—C13	−142.1 (2)
C17—C3—C4—C5	149.3 (2)	C7—C2—C14—C13	−17.1 (2)
C2—C3—C4—C5	24.0 (2)	C3—C2—C14—C13	101.1 (2)
C2—N1—C5—C4	−22.1 (3)	C4—C3—C17—C18	147.6 (2)
C6—N1—C5—C4	−156.7 (2)	C2—C3—C17—C18	−94.1 (2)
N23—C4—C5—N1	−124.4 (2)	C4—C3—C17—C22	−36.1 (3)
C3—C4—C5—N1	−2.8 (3)	C2—C3—C17—C22	82.2 (3)
N1—C2—C7—O16	−36.8 (3)	C22—C17—C18—C19	−0.2 (4)
C14—C2—C7—O16	−166.0 (2)	C3—C17—C18—C19	176.3 (2)
C3—C2—C7—O16	76.7 (3)	C22—C17—C18—Cl1	−179.94 (19)
N1—C2—C7—C8	144.70 (19)	C3—C17—C18—Cl1	−3.5 (3)
C14—C2—C7—C8	15.6 (2)	C17—C18—C19—C20	−0.2 (4)
C3—C2—C7—C8	−101.8 (2)	Cl1—C18—C19—C20	179.6 (2)
O16—C7—C8—C9	−9.0 (4)	C18—C19—C20—C21	−0.1 (5)
C2—C7—C8—C9	169.5 (2)	C19—C20—C21—C22	0.7 (5)
O16—C7—C8—C13	172.9 (3)	C20—C21—C22—C17	−1.2 (5)
C2—C7—C8—C13	−8.6 (3)	C18—C17—C22—C21	0.9 (4)
C13—C8—C9—C10	1.1 (4)	C3—C17—C22—C21	−175.6 (2)
C7—C8—C9—C10	−176.8 (3)	C5—C4—N23—O24	109.1 (4)
C8—C9—C10—C11	0.8 (5)	C3—C4—N23—O24	−9.6 (4)
C9—C10—C11—C12	−1.6 (5)	C5—C4—N23—O25	−68.4 (3)
C10—C11—C12—C13	0.5 (4)	C3—C4—N23—O25	173.0 (3)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
C3—H3···Cl1	0.98	2.59	3.081 (2)	111
C3—H3···O24	0.98	2.30	2.719 (3)	105
C9—H9···O15^i	0.93	2.38	3.109 (3)	135
C21—H21···O16^ii	0.93	2.60	3.248 (3)	127

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