1′-Nitro-2′-(3-nitro­phen­yl)-2′,3′,5′,6′,7′,7a′-hexa­hydro­indan-2-spiro-3′-1′H-pyrrolizine-1,3-dione

In the title compound, C₂₁H₁₇N₃O₆, one of the pyrrolidine ring adopts a twist conformation, while the other is in an envelope conformation. The mol­ecular structure is stabilized by C—H...O and C—H...N intra­molecular inter­actions, and the crystal packing is stabilized by C—H...O inter­molecular inter­actions, generating C(7), C(8) and C(10) chains and an R₂²(10) ring.

Key indicators

• Single-crystal X-ray study
• T = 293 K
• Mean [sigma](C-C) = 0.004 Å
• R factor = 0.060
• wR factor = 0.194
• Data-to-parameter ratio = 16.7

checkCIF/PLATON results

No syntax errors found



Alert level C
PLAT094_ALERT_2_C Ratio of Maximum / Minimum Residual Density ....       2.19
PLAT220_ALERT_2_C Large Non-Solvent    C     Ueq(max)/Ueq(min) ...       2.58 Ratio
PLAT241_ALERT_2_C Check High      Ueq as Compared to Neighbors for         C1
PLAT242_ALERT_2_C Check Low       Ueq as Compared to Neighbors for         N2
PLAT242_ALERT_2_C Check Low       Ueq as Compared to Neighbors for         N3

Alert level G
PLAT199_ALERT_1_G Check the Reported _cell_measurement_temperature        293 K
PLAT200_ALERT_1_G Check the Reported _diffrn_ambient_temperature .        293 K

   0 ALERT level A = In general: serious problem
   0 ALERT level B = Potentially serious problem
   5 ALERT level C = Check and explain
   2 ALERT level G = General alerts; check

   2 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
   5 ALERT type 2 Indicator that the structure model may be wrong or deficient
   0 ALERT type 3 Indicator that the structure quality may be low
   0 ALERT type 4 Improvement, methodology, query or suggestion
   0 ALERT type 5 Informative message, check

---

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: PLATON (Spek, 2003); software used to prepare material for publication: SHELXL97 and PARST (Nardelli, 1995).

1'-Nitro-2'-(3-nitrophenyl)-2',3',5',6',7',7a'-hexahydroindan-2-spiro- 3'-1'H-pyrrolizine-1,3-dione

Crystal data

C21H17N3O6	F(000) = 1696
Mr = 407.38	Dx = 1.422 Mg m^−3
Orthorhombic, Pbcn	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2n 2ab	Cell parameters from 2185 reflections
a = 26.1766 (15) Å	θ = 2.3–28.0°
b = 8.1726 (5) Å	µ = 0.11 mm^−1
c = 17.7838 (10) Å	T = 293 K
V = 3804.5 (4) Å^3	Block, yellow
Z = 8	0.26 × 0.24 × 0.21 mm

Data collection

Bruker SMART APEX CCD diffractometer	3036 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	Rint = 0.026
Graphite monochromator	θmax = 28.0°, θmin = 2.3°
ω scans	h = −34→33
30526 measured reflections	k = −10→10
4520 independent reflections	l = −23→23

Refinement

Refinement on F^2	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F^2 > 2σ(F^2)] = 0.060	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.195	H-atom parameters constrained
S = 1.02	w = 1/[σ^2(Fo^2) + (0.1015P)^2 + 1.0427P] where P = (Fo^2 + 2Fc^2)/3
4520 reflections	(Δ/σ)max = 0.001
271 parameters	Δρmax = 0.41 e Å^−3
0 restraints	Δρmin = −0.19 e Å^−3

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
C1	0.57952 (13)	0.5449 (4)	0.2524 (2)	0.1048 (11)
H1A	0.5437	0.5747	0.2493	0.126*
H1B	0.5977	0.5942	0.2107	0.126*
C2	0.60190 (14)	0.5963 (4)	0.3258 (2)	0.1080 (11)
H2A	0.6100	0.7121	0.3261	0.130*
H2B	0.5790	0.5722	0.3673	0.130*
C3	0.64867 (11)	0.4950 (4)	0.32952 (18)	0.0897 (9)
H3A	0.6603	0.4836	0.3810	0.108*
H3B	0.6758	0.5432	0.2998	0.108*
C4	0.63267 (9)	0.3284 (3)	0.29712 (12)	0.0624 (5)
H4	0.6242	0.2534	0.3383	0.075*
C5	0.67000 (8)	0.2433 (2)	0.24176 (11)	0.0520 (5)
H5	0.6690	0.1250	0.2504	0.062*
C6	0.64935 (7)	0.2793 (2)	0.16423 (10)	0.0468 (4)
H6	0.6593	0.3917	0.1518	0.056*
C7	0.59131 (8)	0.2811 (3)	0.18035 (12)	0.0565 (5)
C8	0.66610 (7)	0.1721 (2)	0.09944 (10)	0.0448 (4)
C9	0.67085 (7)	0.0026 (2)	0.10568 (11)	0.0492 (4)
H9	0.6652	−0.0493	0.1515	0.059*
C10	0.68403 (7)	−0.0862 (2)	0.04307 (12)	0.0529 (5)
C11	0.69335 (8)	−0.0176 (3)	−0.02588 (13)	0.0617 (5)
H11	0.7021	−0.0815	−0.0672	0.074*
C12	0.68931 (9)	0.1500 (3)	−0.03149 (12)	0.0643 (6)
H12	0.6959	0.2009	−0.0772	0.077*
C13	0.67554 (8)	0.2433 (2)	0.02998 (11)	0.0551 (5)
H13	0.6725	0.3561	0.0247	0.066*
C14	0.56706 (8)	0.1100 (3)	0.18843 (13)	0.0620 (5)
C15	0.52226 (8)	0.1035 (3)	0.13853 (13)	0.0698 (6)
C16	0.48735 (11)	−0.0245 (4)	0.12877 (17)	0.0946 (9)
H16	0.4898	−0.1208	0.1564	0.114*
C17	0.44938 (12)	−0.0014 (6)	0.0766 (2)	0.1131 (13)
H17	0.4257	−0.0844	0.0687	0.136*
C18	0.44540 (11)	0.1384 (7)	0.0364 (2)	0.1156 (13)
H18	0.4189	0.1486	0.0019	0.139*
C19	0.47935 (10)	0.2667 (5)	0.04483 (18)	0.0941 (9)
H19	0.4765	0.3622	0.0168	0.113*
C20	0.51810 (8)	0.2452 (4)	0.09759 (14)	0.0722 (7)
C21	0.56005 (9)	0.3589 (3)	0.11630 (15)	0.0693 (6)
N1	0.58597 (7)	0.3644 (3)	0.25275 (11)	0.0676 (5)
N2	0.72315 (7)	0.3039 (3)	0.25456 (11)	0.0673 (5)
N3	0.68717 (8)	−0.2649 (2)	0.05024 (15)	0.0727 (6)
O1	0.74122 (8)	0.4013 (3)	0.21189 (13)	0.1115 (8)
O2	0.74468 (8)	0.2511 (3)	0.30968 (12)	0.1019 (7)
O3	0.68728 (11)	−0.3242 (2)	0.11208 (15)	0.1192 (9)
O4	0.68983 (10)	−0.3462 (2)	−0.00626 (15)	0.1119 (8)
O5	0.58248 (7)	0.0023 (2)	0.22942 (11)	0.0809 (5)
O6	0.56975 (8)	0.4864 (3)	0.08570 (13)	0.1009 (7)

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
C1	0.099 (2)	0.095 (2)	0.120 (2)	0.0442 (17)	−0.0199 (18)	−0.0357 (19)
C2	0.114 (2)	0.089 (2)	0.121 (3)	0.0144 (18)	0.004 (2)	−0.0350 (19)
C3	0.0909 (18)	0.0841 (18)	0.094 (2)	0.0096 (15)	−0.0166 (15)	−0.0330 (15)
C4	0.0741 (14)	0.0626 (13)	0.0505 (11)	0.0013 (10)	0.0054 (10)	0.0018 (9)
C5	0.0569 (11)	0.0502 (10)	0.0491 (10)	0.0003 (8)	−0.0036 (8)	0.0019 (8)
C6	0.0469 (9)	0.0443 (9)	0.0493 (10)	−0.0034 (7)	−0.0031 (8)	0.0036 (7)
C7	0.0500 (10)	0.0574 (11)	0.0621 (12)	−0.0023 (8)	−0.0050 (9)	0.0002 (9)
C8	0.0440 (9)	0.0439 (9)	0.0464 (9)	−0.0052 (7)	−0.0044 (7)	0.0040 (7)
C9	0.0507 (10)	0.0452 (9)	0.0516 (10)	−0.0048 (8)	−0.0043 (8)	0.0075 (8)
C10	0.0462 (9)	0.0427 (10)	0.0698 (13)	−0.0038 (7)	−0.0047 (9)	−0.0031 (9)
C11	0.0597 (12)	0.0673 (13)	0.0581 (12)	−0.0025 (10)	0.0014 (9)	−0.0121 (10)
C12	0.0758 (14)	0.0700 (14)	0.0472 (11)	−0.0047 (11)	0.0069 (10)	0.0077 (10)
C13	0.0638 (12)	0.0474 (10)	0.0542 (11)	−0.0030 (9)	0.0014 (9)	0.0094 (8)
C14	0.0547 (11)	0.0689 (13)	0.0625 (12)	−0.0108 (10)	0.0105 (9)	−0.0009 (11)
C15	0.0483 (11)	0.0939 (17)	0.0673 (13)	−0.0153 (11)	0.0107 (10)	−0.0182 (13)
C16	0.0733 (16)	0.121 (2)	0.0898 (19)	−0.0421 (16)	0.0181 (14)	−0.0235 (17)
C17	0.0627 (17)	0.164 (4)	0.113 (3)	−0.047 (2)	0.0081 (17)	−0.040 (3)
C18	0.0512 (15)	0.189 (4)	0.106 (3)	−0.009 (2)	−0.0119 (15)	−0.042 (3)
C19	0.0587 (14)	0.130 (2)	0.094 (2)	0.0123 (15)	−0.0187 (13)	−0.0204 (18)
C20	0.0482 (11)	0.0945 (18)	0.0741 (15)	0.0053 (11)	−0.0030 (10)	−0.0145 (14)
C21	0.0574 (12)	0.0696 (15)	0.0809 (15)	0.0073 (11)	−0.0148 (11)	−0.0010 (12)
N1	0.0526 (10)	0.0781 (12)	0.0722 (12)	0.0014 (9)	0.0045 (8)	−0.0148 (10)
N2	0.0534 (10)	0.0888 (14)	0.0598 (11)	0.0005 (10)	−0.0069 (8)	−0.0100 (10)
N3	0.0697 (12)	0.0461 (10)	0.1021 (16)	−0.0034 (8)	−0.0017 (11)	−0.0054 (11)
O1	0.0737 (12)	0.157 (2)	0.1040 (15)	−0.0430 (13)	−0.0031 (11)	0.0160 (15)
O2	0.0897 (13)	0.1332 (18)	0.0826 (12)	0.0210 (12)	−0.0397 (11)	−0.0138 (12)
O3	0.189 (3)	0.0486 (10)	0.1201 (18)	−0.0019 (12)	−0.0079 (17)	0.0134 (11)
O4	0.144 (2)	0.0588 (10)	0.1328 (18)	−0.0008 (11)	0.0179 (15)	−0.0339 (12)
O5	0.0865 (12)	0.0732 (11)	0.0831 (12)	−0.0202 (9)	0.0054 (9)	0.0169 (9)
O6	0.1023 (14)	0.0813 (13)	0.1193 (17)	0.0008 (11)	−0.0453 (12)	0.0272 (11)

Geometric parameters (Å, º)

C1—N1	1.485 (4)	C10—C11	1.370 (3)
C1—C2	1.491 (5)	C10—N3	1.469 (3)
C1—H1A	0.97	C11—C12	1.377 (3)
C1—H1B	0.97	C11—H11	0.93
C2—C3	1.479 (4)	C12—C13	1.380 (3)
C2—H2A	0.97	C12—H12	0.93
C2—H2B	0.97	C13—H13	0.93
C3—C4	1.536 (4)	C14—O5	1.212 (3)
C3—H3A	0.97	C14—C15	1.471 (3)
C3—H3B	0.97	C15—C20	1.372 (4)
C4—N1	1.484 (3)	C15—C16	1.400 (4)
C4—C5	1.552 (3)	C16—C17	1.373 (5)
C4—H4	0.98	C16—H16	0.93
C5—N2	1.494 (3)	C17—C18	1.351 (6)
C5—C6	1.510 (3)	C17—H17	0.93
C5—H5	0.98	C18—C19	1.383 (5)
C6—C8	1.512 (3)	C18—H18	0.93
C6—C7	1.546 (3)	C19—C20	1.393 (4)
C6—H6	0.98	C19—H19	0.93
C7—N1	1.463 (3)	C20—C21	1.476 (4)
C7—C21	1.540 (3)	C21—O6	1.203 (3)
C7—C14	1.542 (3)	N2—O1	1.197 (3)
C8—C13	1.387 (3)	N2—O2	1.210 (3)
C8—C9	1.395 (3)	N3—O3	1.201 (3)
C9—C10	1.373 (3)	N3—O4	1.206 (3)
C9—H9	0.93
N1—C1—C2	103.4 (3)	C8—C9—H9	120.6
N1—C1—H1A	111.1	C11—C10—C9	123.64 (18)
C2—C1—H1A	111.1	C11—C10—N3	118.4 (2)
N1—C1—H1B	111.1	C9—C10—N3	117.99 (19)
C2—C1—H1B	111.1	C10—C11—C12	117.3 (2)
H1A—C1—H1B	109.0	C10—C11—H11	121.4
C3—C2—C1	101.9 (2)	C12—C11—H11	121.4
C3—C2—H2A	111.4	C11—C12—C13	120.8 (2)
C1—C2—H2A	111.4	C11—C12—H12	119.6
C3—C2—H2B	111.4	C13—C12—H12	119.6
C1—C2—H2B	111.4	C12—C13—C8	121.35 (18)
H2A—C2—H2B	109.3	C12—C13—H13	119.3
C2—C3—C4	104.7 (2)	C8—C13—H13	119.3
C2—C3—H3A	110.8	O5—C14—C15	127.0 (2)
C4—C3—H3A	110.8	O5—C14—C7	125.3 (2)
C2—C3—H3B	110.8	C15—C14—C7	107.7 (2)
C4—C3—H3B	110.8	C20—C15—C16	120.9 (3)
H3A—C3—H3B	108.9	C20—C15—C14	110.7 (2)
N1—C4—C3	104.38 (19)	C16—C15—C14	128.4 (3)
N1—C4—C5	105.67 (16)	C17—C16—C15	117.0 (4)
C3—C4—C5	117.6 (2)	C17—C16—H16	121.5
N1—C4—H4	109.6	C15—C16—H16	121.5
C3—C4—H4	109.6	C18—C17—C16	122.0 (3)
C5—C4—H4	109.6	C18—C17—H17	119.0
N2—C5—C6	114.07 (16)	C16—C17—H17	119.0
N2—C5—C4	109.95 (16)	C17—C18—C19	122.3 (3)
C6—C5—C4	105.46 (16)	C17—C18—H18	118.9
N2—C5—H5	109.1	C19—C18—H18	118.9
C6—C5—H5	109.1	C18—C19—C20	116.5 (4)
C4—C5—H5	109.1	C18—C19—H19	121.8
C5—C6—C8	118.62 (16)	C20—C19—H19	121.8
C5—C6—C7	100.61 (15)	C15—C20—C19	121.4 (3)
C8—C6—C7	115.55 (15)	C15—C20—C21	110.6 (2)
C5—C6—H6	107.1	C19—C20—C21	127.9 (3)
C8—C6—H6	107.1	O6—C21—C20	126.9 (2)
C7—C6—H6	107.1	O6—C21—C7	125.5 (2)
N1—C7—C21	114.06 (18)	C20—C21—C7	107.6 (2)
N1—C7—C14	107.50 (18)	C7—N1—C4	107.3 (2)
C21—C7—C14	102.98 (18)	C7—N1—C1	118.0 (2)
N1—C7—C6	105.15 (15)	C4—N1—C1	107.0 (2)
C21—C7—C6	112.87 (18)	O1—N2—O2	124.5 (2)
C14—C7—C6	114.43 (17)	O1—N2—C5	119.4 (2)
C13—C8—C9	118.09 (18)	O2—N2—C5	116.0 (2)
C13—C8—C6	119.15 (16)	O3—N3—O4	122.7 (2)
C9—C8—C6	122.72 (16)	O3—N3—C10	118.7 (2)
C10—C9—C8	118.86 (18)	O4—N3—C10	118.6 (2)
C10—C9—H9	120.6
N1—C1—C2—C3	42.8 (4)	C20—C15—C16—C17	0.3 (4)
C1—C2—C3—C4	−38.8 (4)	C14—C15—C16—C17	−178.1 (3)
C2—C3—C4—N1	20.3 (3)	C15—C16—C17—C18	−0.3 (5)
C2—C3—C4—C5	137.0 (3)	C16—C17—C18—C19	0.3 (6)
N1—C4—C5—N2	139.69 (18)	C17—C18—C19—C20	−0.4 (5)
C3—C4—C5—N2	23.7 (3)	C16—C15—C20—C19	−0.3 (4)
N1—C4—C5—C6	16.3 (2)	C14—C15—C20—C19	178.3 (2)
C3—C4—C5—C6	−99.7 (2)	C16—C15—C20—C21	−178.3 (2)
N2—C5—C6—C8	78.7 (2)	C14—C15—C20—C21	0.3 (3)
C4—C5—C6—C8	−160.56 (16)	C18—C19—C20—C15	0.3 (4)
N2—C5—C6—C7	−154.30 (17)	C18—C19—C20—C21	178.0 (3)
C4—C5—C6—C7	−33.55 (19)	C15—C20—C21—O6	173.0 (3)
C5—C6—C7—N1	40.01 (19)	C19—C20—C21—O6	−4.8 (5)
C8—C6—C7—N1	169.04 (16)	C15—C20—C21—C7	−4.3 (3)
C5—C6—C7—C21	164.94 (18)	C19—C20—C21—C7	177.8 (2)
C8—C6—C7—C21	−66.0 (2)	N1—C7—C21—O6	72.7 (3)
C5—C6—C7—C14	−77.7 (2)	C14—C7—C21—O6	−171.2 (3)
C8—C6—C7—C14	51.3 (2)	C6—C7—C21—O6	−47.3 (3)
C5—C6—C8—C13	−141.22 (18)	N1—C7—C21—C20	−109.9 (2)
C7—C6—C8—C13	99.2 (2)	C14—C7—C21—C20	6.2 (2)
C5—C6—C8—C9	41.1 (2)	C6—C7—C21—C20	130.1 (2)
C7—C6—C8—C9	−78.5 (2)	C21—C7—N1—C4	−155.19 (19)
C13—C8—C9—C10	−0.7 (3)	C14—C7—N1—C4	91.3 (2)
C6—C8—C9—C10	177.05 (16)	C6—C7—N1—C4	−31.0 (2)
C8—C9—C10—C11	0.6 (3)	C21—C7—N1—C1	−34.4 (3)
C8—C9—C10—N3	−178.01 (17)	C14—C7—N1—C1	−147.9 (2)
C9—C10—C11—C12	0.3 (3)	C6—C7—N1—C1	89.8 (2)
N3—C10—C11—C12	178.90 (19)	C3—C4—N1—C7	134.0 (2)
C10—C11—C12—C13	−1.1 (3)	C5—C4—N1—C7	9.3 (2)
C11—C12—C13—C8	1.0 (3)	C3—C4—N1—C1	6.4 (3)
C9—C8—C13—C12	−0.1 (3)	C5—C4—N1—C1	−118.2 (2)
C6—C8—C13—C12	−177.89 (19)	C2—C1—N1—C7	−151.5 (2)
N1—C7—C14—O5	−64.7 (3)	C2—C1—N1—C4	−30.6 (3)
C21—C7—C14—O5	174.5 (2)	C6—C5—N2—O1	15.1 (3)
C6—C7—C14—O5	51.7 (3)	C4—C5—N2—O1	−103.1 (3)
N1—C7—C14—C15	114.70 (19)	C6—C5—N2—O2	−166.23 (19)
C21—C7—C14—C15	−6.1 (2)	C4—C5—N2—O2	75.5 (2)
C6—C7—C14—C15	−128.93 (19)	C11—C10—N3—O3	168.1 (2)
O5—C14—C15—C20	−176.8 (2)	C9—C10—N3—O3	−13.2 (3)
C7—C14—C15—C20	3.8 (3)	C11—C10—N3—O4	−11.4 (3)
O5—C14—C15—C16	1.7 (4)	C9—C10—N3—O4	167.2 (2)
C7—C14—C15—C16	−177.7 (2)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
C1—H1B···O6	0.97	2.50	3.014 (4)	113
C3—H3B···O1	0.97	2.59	3.291 (4)	129
C3—H3B···N2	0.97	2.45	2.831 (4)	103
C5—H5···O5	0.98	2.51	3.029 (3)	113
C3—H3A···O4^i	0.97	2.43	3.342 (4)	158
C6—H6···O3^ii	0.98	2.54	3.514 (2)	176
C12—H12···O2^iii	0.93	2.57	3.408 (3)	150
C13—H13···O4^ii	0.93	2.54	3.437 (2)	163
C19—H19···O6^iv	0.93	2.51	3.333 (4)	147

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