4-(2-Nitro­vinyl)-2,3,6,7-tetra­hydro­benzo[1,2-b;4,5-b']difuran

In the structure of the title compound, C₁₂H₁₁NO₄, the two furan rings, one to a greater degree than the other, adopt envelope conformations and are twisted slightly relative to the benzene ring. The olefinic bond displays a trans configuration.

Key indicators

• Single-crystal X-ray study
• T = 296 K
• Mean [sigma](C-C) = 0.003 Å
• R factor = 0.045
• wR factor = 0.102
• Data-to-parameter ratio = 15.5

checkCIF/PLATON results

No syntax errors found



Alert level C
PLAT026_ALERT_3_C Ratio Observed / Unique Reflections too Low ....         40 Perc.
PLAT230_ALERT_2_C Hirshfeld Test Diff for    O1     -   C2      ..       5.07 su
PLAT230_ALERT_2_C Hirshfeld Test Diff for    C3     -   C4      ..       5.90 su
PLAT241_ALERT_2_C Check High      Ueq as Compared to Neighbors for         C3

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

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Computing details

Data collection: PROCESS-AUTO (Rigaku, 1998); cell refinement: PROCESS-AUTO; data reduction: CrystalStructure (Rigaku/MSC, 2004); program(s) used to solve structure: SIR97 (Altomare et al., 1999); program(s) used to refine structure: CRYSTALS (Betteridge et al., 2003); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997); software used to prepare material for publication: CrystalStructure.

4-(2-Nitrovinyl)-2,3,6,7-tetrahydrobenzo[1,2 - b;4,5 - b']difuran

Crystal data

C12H11NO4	F(000) = 488.00
Mr = 233.22	Dx = 1.446 Mg m^−3
Monoclinic, P21/n	Mo Kα radiation, λ = 0.71075 Å
Hall symbol: -P 2yn	Cell parameters from 5880 reflections
a = 10.220 (9) Å	θ = 3.5–27.6°
b = 9.204 (6) Å	µ = 0.11 mm^−1
c = 11.386 (7) Å	T = 296 K
β = 90.08 (3)°	Prism, red
V = 1071.0 (13) Å^3	0.30 × 0.20 × 0.10 mm
Z = 4

Data collection

Rigaku R-AXIS RAPID diffractometer	Rint = 0.048
Detector resolution: 10.00 pixels mm^-1	θmax = 27.5°
ω scans	h = −13→13
9923 measured reflections	k = −11→11
2396 independent reflections	l = −14→13
949 reflections with F^2 > 2.0σ(F^2)

Refinement

Refinement on F^2	w = 1/[0.0001Fo^2 + 0.92σ(Fo^2)]/(4Fo^2)
R[F^2 > 2σ(F^2)] = 0.045	(Δ/σ)max < 0.001
wR(F^2) = 0.102	Δρmax = 0.40 e Å^−3
S = 1.01	Δρmin = −0.36 e Å^−3
2396 reflections	Extinction correction: Larson (1970)
155 parameters	Extinction coefficient: 161 (15)
H-atom parameters constrained

Special details

Geometry. ENTER SPECIAL DETAILS OF THE MOLECULAR GEOMETRY

Refinement. Refinement using all reflections. 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	0.48223 (14)	0.44117 (17)	0.26108 (11)	0.0633 (5)
O2	0.09195 (17)	0.62119 (19)	0.55278 (14)	0.0800 (6)
O3	0.59403 (16)	0.07866 (17)	0.59434 (12)	0.0695 (5)
O4	0.70896 (18)	0.05862 (19)	0.43530 (13)	0.0845 (6)
N1	0.62045 (19)	0.1148 (2)	0.49311 (17)	0.0600 (6)
C1	0.3650 (2)	0.4082 (2)	0.44643 (16)	0.0474 (6)
C2	0.3835 (2)	0.4785 (2)	0.33819 (17)	0.0508 (6)
C3	0.4655 (2)	0.5331 (3)	0.1565 (2)	0.0842 (9)
C4	0.3569 (2)	0.6404 (2)	0.18072 (19)	0.0728 (8)
C5	0.3062 (2)	0.5918 (2)	0.29823 (18)	0.0559 (7)
C6	0.2053 (2)	0.6441 (2)	0.3665 (2)	0.0658 (8)
C7	0.1872 (2)	0.5781 (2)	0.4747 (2)	0.0595 (7)
C8	0.1177 (2)	0.5426 (3)	0.6607 (2)	0.0853 (9)
C9	0.2087 (2)	0.4159 (2)	0.63085 (19)	0.0669 (7)
C10	0.2619 (2)	0.4633 (2)	0.51358 (17)	0.0512 (6)
C11	0.4460 (2)	0.2908 (2)	0.49053 (16)	0.0508 (6)
C12	0.5466 (2)	0.2288 (2)	0.43634 (17)	0.0549 (7)
H32	0.4419	0.4729	0.0898	0.101*
H31	0.5463	0.5842	0.1397	0.101*
H42	0.2891	0.6357	0.1212	0.087*
H41	0.3907	0.7387	0.1852	0.087*
H6	0.1522	0.7201	0.3414	0.079*
H82	0.0361	0.5052	0.6920	0.102*
H81	0.1585	0.6057	0.7183	0.103*
H92	0.1618	0.3246	0.6242	0.080*
H91	0.2787	0.4058	0.6879	0.080*
H11	0.4268	0.2551	0.5649	0.061*
H12	0.5684	0.2598	0.3611	0.066*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
O1	0.0695 (11)	0.0750 (11)	0.0455 (7)	−0.0025 (8)	0.0062 (7)	0.0068 (7)
O2	0.0704 (12)	0.0795 (13)	0.0900 (11)	0.0136 (10)	0.0123 (10)	−0.0064 (9)
O3	0.0819 (12)	0.0653 (10)	0.0612 (9)	0.0028 (9)	−0.0012 (8)	0.0089 (8)
O4	0.0719 (12)	0.0919 (13)	0.0897 (12)	0.0251 (10)	0.0124 (10)	−0.0038 (10)
N1	0.0616 (14)	0.0547 (12)	0.0636 (12)	0.0022 (11)	−0.0008 (10)	−0.0033 (10)
C1	0.0522 (14)	0.0454 (12)	0.0447 (11)	−0.0035 (11)	−0.0020 (10)	−0.0001 (10)
C2	0.0507 (14)	0.0563 (13)	0.0455 (11)	−0.0080 (11)	0.0006 (10)	−0.0062 (10)
C3	0.094 (2)	0.106 (2)	0.0527 (13)	−0.0109 (18)	0.0024 (14)	0.0225 (15)
C4	0.0784 (19)	0.0751 (17)	0.0649 (15)	−0.0147 (15)	−0.0111 (13)	0.0190 (13)
C5	0.0589 (16)	0.0538 (13)	0.0551 (12)	−0.0080 (12)	−0.0108 (11)	0.0070 (11)
C6	0.0623 (17)	0.0582 (15)	0.0770 (16)	0.0015 (13)	−0.0108 (13)	0.0020 (12)
C7	0.0516 (15)	0.0624 (15)	0.0646 (13)	−0.0011 (12)	0.0032 (11)	−0.0079 (13)
C8	0.079 (2)	0.100 (2)	0.0775 (17)	0.0052 (17)	0.0171 (15)	−0.0120 (16)
C9	0.0671 (17)	0.0743 (16)	0.0593 (13)	−0.0002 (14)	0.0138 (12)	−0.0024 (13)
C10	0.0519 (15)	0.0514 (13)	0.0505 (11)	−0.0025 (11)	0.0025 (10)	−0.0036 (10)
C11	0.0593 (15)	0.0476 (13)	0.0455 (11)	−0.0076 (11)	0.0004 (10)	−0.0009 (10)
C12	0.0602 (16)	0.0532 (14)	0.0514 (12)	0.0003 (12)	−0.0016 (11)	0.0040 (10)

Geometric parameters (Å, º)

O1—C2	1.382 (2)	C7—C10	1.376 (3)
O1—C3	1.471 (2)	C8—C9	1.530 (3)
O2—C7	1.378 (2)	C9—C10	1.507 (2)
O2—C8	1.450 (3)	C11—C12	1.329 (3)
O3—N1	1.230 (2)	C3—H32	0.970
O4—N1	1.233 (2)	C3—H31	0.970
N1—C12	1.444 (2)	C4—H42	0.970
C1—C2	1.405 (2)	C4—H41	0.970
C1—C10	1.398 (2)	C6—H6	0.930
C1—C11	1.450 (2)	C8—H82	0.970
C2—C5	1.385 (3)	C8—H81	0.970
C3—C4	1.511 (3)	C9—H92	0.970
C4—C5	1.504 (3)	C9—H91	0.970
C5—C6	1.380 (3)	C11—H11	0.930
C6—C7	1.386 (3)	C12—H12	0.930
O2···O2^i	3.154 (2)	C11···H42^xiv	3.069
O2···O4^ii	3.584 (2)	C12···H42^xiv	3.596
O2···C4^iii	3.566 (3)	C12···H82^viii	3.520
O2···C7^i	3.406 (2)	H32···O3^xi	3.587
O2···C8^i	3.572 (3)	H32···O4^xi	2.973
O3···O3^iv	3.224 (2)	H32···N1^xi	3.556
O3···O4^iv	3.361 (2)	H32···C3^xv	2.962
O3···N1^iv	2.994 (2)	H32···C6^xiv	3.416
O3···C4^v	3.499 (2)	H32···H32^xv	2.419
O3···C5^ii	3.425 (2)	H32···H31^xv	2.668
O3···C5^v	3.541 (2)	H32···H6^xiv	2.637
O3···C6^ii	3.304 (2)	H32···H92^viii	3.564
O3···C8^vi	3.548 (3)	H31···O2^x	2.924
O3···C11^iv	3.559 (2)	H31···O4^ix	2.654
O3···C12^iv	3.193 (2)	H31···C3^xv	3.543
O4···O2^ii	3.584 (2)	H31···C8^x	3.520
O4···O3^iv	3.361 (2)	H31···H32^xv	2.668
O4···C3^vii	3.497 (3)	H31···H81^x	3.203
O4···C8^viii	3.391 (3)	H31···H91^ii	2.656
O4···C9^viii	3.474 (2)	H42···O3^xi	2.821
N1···O3^iv	2.994 (2)	H42···O4^xi	2.889
N1···N1^iv	3.249 (2)	H42···N1^xi	3.226
N1···C6^ii	3.262 (3)	H42···C1^xvi	3.059
N1···C7^ii	3.462 (2)	H42···C10^xvi	3.423
C1···C1^ii	3.457 (2)	H42···C11^xvi	3.069
C1···C11^ii	3.452 (2)	H42···C12^xvi	3.596
C2···C11^ii	3.367 (2)	H42···H92^xvi	3.329
C3···O4^ix	3.497 (3)	H42···H11^xvi	3.249
C4···O2^x	3.566 (3)	H41···O2^x	2.859
C4···O3^xi	3.499 (2)	H41···O3^ii	3.025
C5···O3^ii	3.425 (2)	H41···C1^xvi	3.391
C5···O3^xi	3.541 (2)	H41···C2^xvi	3.577
C6···O3^ii	3.304 (2)	H41···C8^x	3.084
C6···N1^ii	3.262 (3)	H41···C10^xvi	3.438
C6···C12^ii	3.580 (3)	H41···H82^x	2.787
C7···O2^i	3.406 (2)	H41···H81^x	3.111
C7···N1^ii	3.462 (2)	H41···H11^ii	3.400
C7···C12^ii	3.402 (3)	H6···O1^xvi	2.717
C8···O2^i	3.572 (3)	H6···O3^ii	3.269
C8···O3^xii	3.548 (3)	H6···O4^ii	3.552
C8···O4^xiii	3.391 (3)	H6···N1^ii	3.353
C9···O4^xiii	3.474 (2)	H6···C2^xvi	3.157
C10···C12^ii	3.490 (3)	H6···C3^xvi	3.122
C11···O3^iv	3.559 (2)	H6···H32^xvi	2.637
C11···C1^ii	3.452 (2)	H6···H82^i	2.855
C11···C2^ii	3.367 (2)	H6···H92^i	3.260
C12···O3^iv	3.193 (2)	H6···H12^xvi	3.243
C12···C6^ii	3.580 (3)	H82···O2^i	3.291
C12···C7^ii	3.402 (3)	H82···O3^xii	2.855
C12···C10^ii	3.490 (3)	H82···O4^xiii	3.335
O1···H6^xiv	2.717	H82···C6^i	2.901
O1···H92^viii	3.434	H82···C7^i	3.064
O1···H91^ii	2.879	H82···C12^xiii	3.520
O1···H11^ii	3.549	H82···H41^iii	2.787
O2···H31^iii	2.924	H82···H6^i	2.855
O2···H41^iii	2.859	H82···H12^xiii	3.124
O2···H82^i	3.291	H81···O3^xii	3.360
O2···H92^i	3.320	H81···O4^xiii	2.942
O3···H32^v	3.587	H81···C9^xii	3.597
O3···H42^v	2.821	H81···H31^iii	3.203
O3···H41^ii	3.025	H81···H41^iii	3.111
O3···H6^ii	3.269	H81···H92^xii	3.262
O3···H82^vi	2.855	H81···H91^xii	3.030
O3···H81^vi	3.360	H81···H11^xii	2.958
O3···H11^iv	3.574	H81···H12^ii	3.185
O3···H12^iv	3.566	H92···O1^xiii	3.434
O4···H32^v	2.973	H92···O2^i	3.320
O4···H31^vii	2.654	H92···H32^xiii	3.564
O4···H42^v	2.889	H92···H42^xiv	3.329
O4···H6^ii	3.552	H92···H6^i	3.260
O4···H82^viii	3.335	H92···H81^vi	3.262
O4···H81^viii	2.942	H92···H12^xiii	2.966
O4···H91^viii	2.925	H91···O1^ii	2.879
O4···H11^iv	3.204	H91···O4^xiii	2.925
N1···H32^v	3.556	H91···C3^ii	3.206
N1···H42^v	3.226	H91···H31^ii	2.656
N1···H6^ii	3.353	H91···H81^vi	3.030
N1···H11^iv	3.502	H91···H12^ii	3.497
C1···H42^xiv	3.059	H91···H12^xiii	3.293
C1···H41^xiv	3.391	H11···O1^ii	3.549
C2···H41^xiv	3.577	H11···O3^iv	3.574
C2···H6^xiv	3.157	H11···O4^iv	3.204
C2···H11^ii	3.314	H11···N1^iv	3.502
C3···H32^xv	2.962	H11···C2^ii	3.314
C3···H31^xv	3.543	H11···C5^ii	3.442
C3···H6^xiv	3.122	H11···H42^xiv	3.249
C3···H91^ii	3.206	H11···H41^ii	3.400
C5···H11^ii	3.442	H11···H81^vi	2.958
C6···H32^xvi	3.416	H12···O3^iv	3.566
C6···H82^i	2.901	H12···C7^ii	3.457
C7···H82^i	3.064	H12···C9^viii	3.399
C7···H12^ii	3.457	H12···C10^ii	3.396
C8···H31^iii	3.520	H12···H6^xiv	3.243
C8···H41^iii	3.084	H12···H82^viii	3.124
C9···H81^vi	3.597	H12···H81^ii	3.185
C9···H12^xiii	3.399	H12···H92^viii	2.966
C10···H42^xiv	3.423	H12···H91^ii	3.497
C10···H41^xiv	3.438	H12···H91^viii	3.293
C10···H12^ii	3.396
C2—O1—C3	106.68 (17)	O1—C3—H32	109.5
C7—O2—C8	106.00 (18)	O1—C3—H31	109.9
O3—N1—O4	123.28 (18)	C4—C3—H32	109.5
O3—N1—C12	120.05 (18)	C4—C3—H31	110.2
O4—N1—C12	116.67 (18)	H32—C3—H31	109.5
C2—C1—C10	114.50 (18)	C3—C4—H42	111.6
C2—C1—C11	124.71 (18)	C3—C4—H41	110.9
C10—C1—C11	120.76 (17)	C5—C4—H42	111.2
O1—C2—C1	122.82 (18)	C5—C4—H41	110.8
O1—C2—C5	113.28 (17)	H42—C4—H41	109.5
C1—C2—C5	123.90 (19)	C5—C6—H6	121.7
O1—C3—C4	108.26 (18)	C7—C6—H6	121.7
C3—C4—C5	102.79 (19)	O2—C8—H82	109.5
C2—C5—C4	108.65 (19)	O2—C8—H81	110.5
C2—C5—C6	120.30 (19)	C9—C8—H82	109.5
C4—C5—C6	131.0 (2)	C9—C8—H81	110.2
C5—C6—C7	116.6 (2)	H82—C8—H81	109.5
O2—C7—C6	122.8 (2)	C8—C9—H92	112.2
O2—C7—C10	113.89 (19)	C8—C9—H91	111.8
C6—C7—C10	123.3 (2)	C10—C9—H92	111.1
O2—C8—C9	107.55 (19)	C10—C9—H91	110.8
C8—C9—C10	101.31 (18)	H92—C9—H91	109.5
C1—C10—C7	121.37 (18)	C1—C11—H11	117.3
C1—C10—C9	130.70 (19)	C12—C11—H11	115.8
C7—C10—C9	107.91 (19)	N1—C12—H12	120.6
C1—C11—C12	126.94 (18)	C11—C12—H12	118.8
N1—C12—C11	120.55 (18)
C2—O1—C3—C4	5.7 (2)	O1—C2—C5—C6	−178.5 (2)
C3—O1—C2—C1	177.2 (2)	C1—C2—C5—C4	179.0 (2)
C3—O1—C2—C5	−3.2 (2)	C1—C2—C5—C6	1.2 (3)
C7—O2—C8—C9	−17.0 (2)	O1—C3—C4—C5	−5.8 (2)
C8—O2—C7—C6	−171.3 (2)	C3—C4—C5—C2	4.0 (2)
C8—O2—C7—C10	9.1 (2)	C3—C4—C5—C6	−178.5 (2)
O3—N1—C12—C11	−3.2 (3)	C2—C5—C6—C7	0.2 (3)
O4—N1—C12—C11	177.1 (2)	C4—C5—C6—C7	−177.1 (2)
C2—C1—C10—C7	−0.5 (3)	C5—C6—C7—O2	178.7 (2)
C2—C1—C10—C9	177.9 (2)	C5—C6—C7—C10	−1.7 (3)
C10—C1—C2—O1	178.60 (18)	O2—C7—C10—C1	−178.41 (19)
C10—C1—C2—C5	−1.0 (3)	O2—C7—C10—C9	2.8 (2)
C2—C1—C11—C12	−1.9 (3)	C6—C7—C10—C1	2.0 (3)
C11—C1—C2—O1	0.5 (3)	C6—C7—C10—C9	−176.8 (2)
C11—C1—C2—C5	−179.1 (2)	O2—C8—C9—C10	17.9 (2)
C10—C1—C11—C12	−179.8 (2)	C8—C9—C10—C1	168.8 (2)
C11—C1—C10—C7	177.6 (2)	C8—C9—C10—C7	−12.6 (2)
C11—C1—C10—C9	−3.9 (3)	C1—C11—C12—N1	178.40 (19)
O1—C2—C5—C4	−0.6 (2)

Symmetry codes: (i) −x, −y+1, −z+1; (ii) −x+1, −y+1, −z+1; (iii) x−1/2, −y+3/2, z+1/2; (iv) −x+1, −y, −z+1; (v) x+1/2, −y+1/2, z+1/2; (vi) −x+1/2, y−1/2, −z+3/2; (vii) −x+3/2, y−1/2, −z+1/2; (viii) x+1/2, −y+1/2, z−1/2; (ix) −x+3/2, y+1/2, −z+1/2; (x) x+1/2, −y+3/2, z−1/2; (xi) x−1/2, −y+1/2, z−1/2; (xii) −x+1/2, y+1/2, −z+3/2; (xiii) x−1/2, −y+1/2, z+1/2; (xiv) −x+1/2, y−1/2, −z+1/2; (xv) −x+1, −y+1, −z; (xvi) −x+1/2, y+1/2, −z+1/2.