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The title compound, C34H28N4O10·2C3H7NO, was synthesized by the reaction of eth­yl 2-cyano-3-(3-nitro­phen­yl)-1-acrylate and 1,5-naphthalene­diol in the presence of KF-Al2O3 in refluxing ethanol. The structure is centrosymmetric and the fused pyran ring adopts a boat conformation.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536805017113/ob6529sup1.cif
Contains datablocks global, I

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536805017113/ob6529Isup2.hkl
Contains datablock I

CCDC reference: 277737

Key indicators

  • Single-crystal X-ray study
  • T = 289 K
  • Mean [sigma](C-C) = 0.004 Å
  • R factor = 0.071
  • wR factor = 0.242
  • Data-to-parameter ratio = 12.2

checkCIF/PLATON results

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Alert level B PLAT230_ALERT_2_B Hirshfeld Test Diff for C10 - C11 .. 9.17 su
Alert level C PLAT042_ALERT_1_C Calc. and Rep. MoietyFormula Strings Differ .... ? PLAT220_ALERT_2_C Large Non-Solvent C Ueq(max)/Ueq(min) ... 2.56 Ratio PLAT220_ALERT_2_C Large Non-Solvent O Ueq(max)/Ueq(min) ... 2.74 Ratio PLAT242_ALERT_2_C Check Low Ueq as Compared to Neighbors for C10 PLAT244_ALERT_4_C Low 'Solvent' Ueq as Compared to Neighbors for N3 PLAT731_ALERT_1_C Bond Calc 0.86(3), Rep 0.859(10) ...... 3.00 su-Rat N1 -H1B 1.555 1.555 PLAT735_ALERT_1_C D-H Calc 0.86(3), Rep 0.859(10) ...... 3.00 su-Rat N1 -H1B 1.555 1.555 PLAT736_ALERT_1_C H...A Calc 2.02(3), Rep 2.015(13) ...... 2.31 su-Rat H1B -O6 1.555 1.555
0 ALERT level A = In general: serious problem 1 ALERT level B = Potentially serious problem 8 ALERT level C = Check and explain 0 ALERT level G = General alerts; check 4 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 0 ALERT type 3 Indicator that the structure quality may be low 1 ALERT type 4 Improvement, methodology, query or suggestion

Computing details top

Data collection: XSCANS (Siemens, 1994); cell refinement: XSCANS; data reduction: SHELXTL (Sheldrick, 1997); program(s) used to solve structure: SHELXTL; program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL.

Diethyl 2,8-diamino-4,10-bis(3-nitrophenyl)naphtha[1,2 - b;6,5 - b']dipyran- 3,9-dicarboxylate dimethylformamide disolvate top
Crystal data top
C34H28N4O10·2C3H7NOZ = 1
Mr = 798.80F(000) = 420
Triclinic, P1Dx = 1.377 Mg m3
Hall symbol: -P 1Melting point = 559–561 K
a = 8.355 (1) ÅMo Kα radiation, λ = 0.71073 Å
b = 9.750 (1) ÅCell parameters from 26 reflections
c = 12.202 (2) Åθ = 3.3–29.6°
α = 99.292 (3)°µ = 0.10 mm1
β = 96.912 (3)°T = 289 K
γ = 97.103 (3)°Block, yellow
V = 963.4 (2) Å30.34 × 0.24 × 0.18 mm
Data collection top
Siemens P4
diffractometer
Rint = 0.022
Radiation source: normal-focus sealed tubeθmax = 25.0°, θmin = 1.7°
Graphite monochromatorh = 99
ω scansk = 1111
5054 measured reflectionsl = 148
3340 independent reflections3 standard reflections every 97 reflections
2241 reflections with I > 2σ(I) intensity decay: 2.3%
Refinement top
Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.071Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.242H atoms treated by a mixture of independent and constrained refinement
S = 1.02 w = 1/[σ2(Fo2) + (0.16P)2]
where P = (Fo2 + 2Fc2)/3
3340 reflections(Δ/σ)max < 0.001
273 parametersΔρmax = 0.42 e Å3
2 restraintsΔρmin = 0.32 e Å3
Special details top

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 (Å2) top
xyzUiso*/Ueq
O10.2720 (2)0.33760 (19)0.54942 (16)0.0541 (6)
O20.7598 (2)0.5894 (2)0.75623 (17)0.0615 (6)
O30.7614 (2)0.3615 (2)0.68959 (18)0.0670 (6)
O40.6779 (4)0.9562 (4)1.0344 (3)0.1178 (11)
O50.5458 (5)0.9030 (5)1.1671 (3)0.1482 (15)
N10.4824 (3)0.2222 (3)0.5621 (2)0.0673 (8)
N20.5741 (5)0.8809 (5)1.0713 (3)0.1006 (11)
C10.4318 (3)0.3454 (3)0.5917 (2)0.0506 (7)
C20.5197 (3)0.4645 (3)0.6550 (2)0.0500 (7)
C30.4431 (3)0.5960 (3)0.6861 (2)0.0481 (7)
H30.51470.67680.67200.058*
C40.2783 (3)0.5847 (3)0.6150 (2)0.0458 (7)
C50.2013 (3)0.4587 (3)0.5568 (2)0.0443 (6)
C60.0395 (3)0.4396 (3)0.4986 (2)0.0442 (7)
C70.0439 (3)0.3078 (3)0.4415 (2)0.0503 (7)
H70.00650.22790.44190.060*
C80.1972 (3)0.2969 (3)0.3861 (2)0.0501 (7)
H80.24990.20950.34800.060*
C90.6884 (3)0.4624 (3)0.6987 (2)0.0537 (7)
C100.9266 (3)0.5975 (4)0.8062 (3)0.0644 (9)
H10A0.99300.56570.74990.077*
H10B0.93420.54000.86390.077*
C110.9802 (5)0.7468 (5)0.8548 (4)0.1124 (15)
H11A0.96420.80260.79750.135*
H11B1.09370.76030.88510.135*
H11C0.91770.77480.91350.135*
C120.4220 (3)0.6202 (3)0.8102 (2)0.0495 (7)
C130.3248 (3)0.5227 (3)0.8526 (3)0.0585 (8)
H130.27170.44160.80470.070*
C140.3042 (4)0.5424 (5)0.9638 (3)0.0761 (10)
H140.23690.47550.99000.091*
C150.3828 (5)0.6606 (5)1.0361 (3)0.0812 (11)
H150.36900.67541.11140.097*
C160.4813 (4)0.7552 (4)0.9948 (3)0.0700 (9)
C170.5021 (3)0.7387 (3)0.8840 (3)0.0615 (8)
H170.56940.80640.85850.074*
O60.2412 (5)0.0044 (4)0.4304 (4)0.1433 (16)
N30.0765 (4)0.0776 (3)0.2691 (3)0.0800 (9)
C180.2132 (7)0.0243 (6)0.3366 (6)0.1238 (18)
H180.30280.00740.29960.149*
C190.0632 (7)0.1170 (7)0.3137 (5)0.145 (2)
H19A0.08360.21750.30490.174*
H19B0.15400.08420.27510.174*
H19C0.04890.07650.39200.174*
C200.0655 (8)0.1314 (7)0.1510 (5)0.155 (2)
H20A0.16310.09600.12430.186*
H20B0.02670.10190.11120.186*
H20C0.05270.23220.13880.186*
H1A0.5800 (18)0.211 (3)0.586 (2)0.066 (9)*
H1B0.420 (4)0.153 (3)0.519 (2)0.082 (12)*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
O10.0377 (10)0.0564 (12)0.0684 (13)0.0156 (8)0.0030 (8)0.0130 (9)
O20.0330 (10)0.0795 (15)0.0700 (14)0.0123 (9)0.0002 (9)0.0098 (11)
O30.0435 (11)0.0838 (15)0.0766 (15)0.0276 (10)0.0021 (10)0.0143 (11)
O40.095 (2)0.121 (3)0.120 (3)0.0107 (19)0.0029 (19)0.011 (2)
O50.158 (3)0.201 (4)0.067 (2)0.033 (3)0.006 (2)0.027 (2)
N10.0479 (16)0.0686 (18)0.083 (2)0.0254 (14)0.0057 (14)0.0062 (15)
N20.089 (3)0.132 (3)0.073 (2)0.040 (2)0.0072 (19)0.010 (2)
C10.0387 (14)0.0648 (18)0.0512 (16)0.0147 (13)0.0027 (12)0.0162 (14)
C20.0370 (14)0.0679 (18)0.0506 (16)0.0169 (13)0.0074 (11)0.0185 (14)
C30.0356 (13)0.0609 (16)0.0496 (16)0.0079 (12)0.0054 (11)0.0155 (13)
C40.0359 (14)0.0591 (17)0.0458 (15)0.0108 (12)0.0051 (11)0.0168 (13)
C50.0362 (13)0.0553 (16)0.0454 (15)0.0113 (11)0.0051 (11)0.0177 (12)
C60.0363 (14)0.0568 (17)0.0436 (14)0.0125 (11)0.0062 (11)0.0161 (12)
C70.0456 (15)0.0525 (16)0.0562 (17)0.0156 (12)0.0044 (12)0.0155 (13)
C80.0412 (14)0.0520 (16)0.0573 (17)0.0078 (12)0.0015 (12)0.0142 (13)
C90.0386 (15)0.077 (2)0.0501 (16)0.0140 (14)0.0080 (12)0.0207 (15)
C100.0367 (15)0.093 (2)0.0621 (19)0.0096 (14)0.0001 (13)0.0133 (17)
C110.078 (3)0.137 (4)0.113 (4)0.029 (3)0.004 (2)0.003 (3)
C120.0357 (13)0.0653 (17)0.0498 (16)0.0186 (12)0.0008 (11)0.0129 (13)
C130.0480 (16)0.0728 (19)0.0609 (19)0.0147 (14)0.0122 (13)0.0226 (15)
C140.064 (2)0.108 (3)0.074 (2)0.0321 (19)0.0225 (17)0.043 (2)
C150.078 (2)0.130 (3)0.0484 (19)0.051 (2)0.0142 (18)0.022 (2)
C160.062 (2)0.097 (3)0.0515 (19)0.0329 (18)0.0036 (15)0.0069 (18)
C170.0487 (16)0.076 (2)0.0612 (19)0.0192 (14)0.0010 (13)0.0147 (16)
O60.152 (3)0.126 (3)0.125 (3)0.026 (2)0.041 (3)0.018 (2)
N30.074 (2)0.081 (2)0.084 (2)0.0170 (15)0.0022 (17)0.0181 (16)
C180.121 (4)0.103 (4)0.147 (5)0.048 (3)0.009 (4)0.018 (4)
C190.127 (4)0.167 (5)0.131 (5)0.031 (4)0.019 (4)0.035 (4)
C200.176 (6)0.188 (6)0.105 (4)0.063 (5)0.018 (4)0.008 (4)
Geometric parameters (Å, º) top
O1—C11.360 (3)C10—H10A0.9700
O1—C51.379 (3)C10—H10B0.9700
O2—C91.348 (4)C11—H11A0.9600
O2—C101.440 (3)C11—H11B0.9600
O3—C91.218 (4)C11—H11C0.9600
O4—N21.240 (5)C12—C131.378 (4)
O5—N21.212 (4)C12—C171.386 (4)
N1—C11.332 (4)C13—C141.374 (5)
N1—H1A0.859 (10)C13—H130.9300
N1—H1B0.859 (10)C14—C151.372 (6)
N2—C161.481 (5)C14—H140.9300
C1—C21.359 (4)C15—C161.358 (5)
C2—C91.450 (4)C15—H150.9300
C2—C31.518 (4)C16—C171.371 (4)
C3—C41.518 (3)C17—H170.9300
C3—C121.529 (4)O6—C181.122 (6)
C3—H30.9800N3—C181.320 (6)
C4—C51.357 (4)N3—C191.384 (5)
C4—C8i1.410 (4)N3—C201.439 (6)
C5—C61.425 (4)C18—H180.9300
C6—C71.412 (4)C19—H19A0.9600
C6—C6i1.417 (5)C19—H19B0.9600
C7—C81.358 (4)C19—H19C0.9600
C7—H70.9300C20—H20A0.9600
C8—C4i1.410 (4)C20—H20B0.9600
C8—H80.9300C20—H20C0.9600
C10—C111.472 (6)
C1—O1—C5119.3 (2)H10A—C10—H10B108.8
C9—O2—C10115.8 (2)C10—C11—H11A109.5
C1—N1—H1A120 (2)C10—C11—H11B109.5
C1—N1—H1B122 (3)H11A—C11—H11B109.5
H1A—N1—H1B118 (3)C10—C11—H11C109.5
O5—N2—O4123.7 (4)H11A—C11—H11C109.5
O5—N2—C16117.9 (4)H11B—C11—H11C109.5
O4—N2—C16118.4 (4)C13—C12—C17117.9 (3)
N1—C1—C2127.6 (3)C13—C12—C3120.7 (3)
N1—C1—O1109.9 (2)C17—C12—C3121.4 (3)
C2—C1—O1122.5 (2)C14—C13—C12121.7 (3)
C1—C2—C9118.7 (3)C14—C13—H13119.2
C1—C2—C3121.7 (2)C12—C13—H13119.2
C9—C2—C3119.5 (3)C15—C14—C13120.1 (3)
C2—C3—C4110.4 (2)C15—C14—H14119.9
C2—C3—C12111.0 (2)C13—C14—H14119.9
C4—C3—C12109.29 (19)C16—C15—C14118.2 (3)
C2—C3—H3108.7C16—C15—H15120.9
C4—C3—H3108.7C14—C15—H15120.9
C12—C3—H3108.7C15—C16—C17122.7 (3)
C5—C4—C8i118.5 (2)C15—C16—N2119.9 (3)
C5—C4—C3120.7 (2)C17—C16—N2117.5 (3)
C8i—C4—C3120.7 (2)C16—C17—C12119.4 (3)
C4—C5—O1123.1 (2)C16—C17—H17120.3
C4—C5—C6122.9 (2)C12—C17—H17120.3
O1—C5—C6114.0 (2)C18—N3—C19119.8 (5)
C7—C6—C6i119.8 (3)C18—N3—C20124.9 (5)
C7—C6—C5123.3 (2)C19—N3—C20113.5 (5)
C6i—C6—C5116.9 (3)O6—C18—N3131.8 (7)
C8—C7—C6120.4 (2)O6—C18—H18114.1
C8—C7—H7119.8N3—C18—H18114.1
C6—C7—H7119.8N3—C19—H19A109.5
C7—C8—C4i121.4 (3)N3—C19—H19B109.5
C7—C8—H8119.3H19A—C19—H19B109.5
C4i—C8—H8119.3N3—C19—H19C109.5
O3—C9—O2121.7 (2)H19A—C19—H19C109.5
O3—C9—C2126.8 (3)H19B—C19—H19C109.5
O2—C9—C2111.4 (2)N3—C20—H20A109.5
O2—C10—C11105.4 (3)N3—C20—H20B109.5
O2—C10—H10A110.7H20A—C20—H20B109.5
C11—C10—H10A110.7N3—C20—H20C109.5
O2—C10—H10B110.7H20A—C20—H20C109.5
C11—C10—H10B110.7H20B—C20—H20C109.5
C5—O1—C1—N1171.0 (2)C10—O2—C9—O30.3 (4)
C5—O1—C1—C29.4 (4)C10—O2—C9—C2178.2 (2)
N1—C1—C2—C90.9 (5)C1—C2—C9—O33.8 (4)
O1—C1—C2—C9178.7 (2)C3—C2—C9—O3172.8 (3)
N1—C1—C2—C3177.4 (3)C1—C2—C9—O2177.9 (2)
O1—C1—C2—C32.1 (4)C3—C2—C9—O25.5 (3)
C1—C2—C3—C413.9 (4)C9—O2—C10—C11175.3 (3)
C9—C2—C3—C4169.6 (2)C2—C3—C12—C1361.3 (3)
C1—C2—C3—C12107.5 (3)C4—C3—C12—C1360.7 (3)
C9—C2—C3—C1269.1 (3)C2—C3—C12—C17117.3 (3)
C2—C3—C4—C515.8 (3)C4—C3—C12—C17120.7 (3)
C12—C3—C4—C5106.6 (3)C17—C12—C13—C141.3 (4)
C2—C3—C4—C8i168.4 (2)C3—C12—C13—C14180.0 (2)
C12—C3—C4—C8i69.2 (3)C12—C13—C14—C150.8 (5)
C8i—C4—C5—O1177.8 (2)C13—C14—C15—C160.6 (5)
C3—C4—C5—O16.3 (4)C14—C15—C16—C171.4 (5)
C8i—C4—C5—C62.8 (4)C14—C15—C16—N2177.2 (3)
C3—C4—C5—C6173.1 (2)O5—N2—C16—C157.6 (5)
C1—O1—C5—C47.2 (4)O4—N2—C16—C15171.2 (3)
C1—O1—C5—C6173.2 (2)O5—N2—C16—C17173.6 (3)
C4—C5—C6—C7177.4 (2)O4—N2—C16—C177.5 (5)
O1—C5—C6—C72.2 (4)C15—C16—C17—C120.9 (4)
C4—C5—C6—C6i1.3 (4)N2—C16—C17—C12177.8 (3)
O1—C5—C6—C6i179.2 (3)C13—C12—C17—C160.5 (4)
C6i—C6—C7—C82.4 (4)C3—C12—C17—C16179.2 (2)
C5—C6—C7—C8179.0 (2)C19—N3—C18—O64.6 (8)
C6—C7—C8—C4i0.9 (4)C20—N3—C18—O6168.6 (6)
Symmetry code: (i) x, y+1, z+1.
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N1—H1A···O30.86 (1)2.11 (3)2.713 (3)127 (3)
N1—H1B···O60.86 (1)2.02 (1)2.866 (5)170 (4)
 

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