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The crystal structure of the title compound, C21H19N3O7·2C3H7NO, has been prepared, for the first time in the dark, as the permanent merocyanine mode of the open form. It has a zwitterionic transtransoid structure and is solvated with two N,N-di­methyl­form­amide (DMF) mol­ecules, forming O—H...O and C—H...O hydrogen bonds. The crystal structure is further stabilized by a variety of weak C—H...O hydrogen bonds.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536803003337/ac6029sup1.cif
Contains datablocks global, I

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536803003337/ac6029Isup2.hkl
Contains datablock I

CCDC reference: 206785

Key indicators

  • Single-crystal X-ray study
  • T = 293 K
  • Mean [sigma](C-C) = 0.005 Å
  • R factor = 0.063
  • wR factor = 0.153
  • Data-to-parameter ratio = 13.2

checkCIF results

No syntax errors found

ADDSYM reports no extra symmetry








Computing details top

Data collection: SMART (Bruker, 1998); cell refinement: SMART; data reduction: SAINT (Bruker, 1998); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: SHELXTL (Bruker, 1997); software used to prepare material for publication: SHELXTL.

1'-(2-Carboxyethyl)-3',3'-dimethyl-6,8-dinitrospiro[2H-1-benzopyran- 2,2'(2H)-indole] bis(dimethylformamide) solvate top
Crystal data top
C21H19N3O7·2C3H7NOZ = 2
Mr = 571.58F(000) = 604
Triclinic, P1Dx = 1.331 Mg m3
a = 10.633 (4) ÅMo Kα radiation, λ = 0.71073 Å
b = 12.078 (4) ÅCell parameters from 636 reflections
c = 12.262 (4) Åθ = 2.8–22.4°
α = 113.266 (6)°µ = 0.10 mm1
β = 95.167 (6)°T = 293 K
γ = 95.326 (6)°Plate, red
V = 1426.6 (9) Å30.24 × 0.22 × 0.16 mm
Data collection top
Bruker SMART CCD area-detector
diffractometer
4991 independent reflections
Radiation source: fine-focus sealed tube2331 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.039
φ and ω scansθmax = 25.0°, θmin = 1.8°
Absorption correction: multi-scan
(SADABS; Sheldrick, 1996)
h = 1212
Tmin = 0.958, Tmax = 1.000k = 1314
7300 measured reflectionsl = 1314
Refinement top
Refinement on F2Secondary atom site location: difference Fourier map
Least-squares matrix: fullHydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.063H-atom parameters constrained
wR(F2) = 0.153 w = 1/[σ2(Fo2) + (0.0559P)2]
where P = (Fo2 + 2Fc2)/3
S = 1.00(Δ/σ)max = 0.001
4991 reflectionsΔρmax = 0.17 e Å3
378 parametersΔρmin = 0.18 e Å3
124 restraintsExtinction correction: SHELXL97, Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
Primary atom site location: structure-invariant direct methodsExtinction coefficient: none
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
N10.8221 (2)0.5872 (3)0.6455 (2)0.0364 (7)
N20.4743 (3)0.2938 (3)1.0985 (3)0.0555 (9)
N30.2492 (3)0.2666 (3)0.7288 (3)0.0560 (9)
O10.7001 (2)0.3953 (3)1.0368 (2)0.0637 (8)
O20.5468 (3)0.3575 (3)1.1892 (3)0.0756 (9)
O30.3909 (4)0.2175 (3)1.0976 (3)0.1048 (13)
O40.1564 (2)0.2163 (3)0.7517 (3)0.0788 (10)
O50.2459 (2)0.2866 (3)0.6379 (3)0.0789 (10)
O60.4908 (2)0.6710 (3)0.4957 (2)0.0620 (8)
O70.5527 (3)0.8665 (3)0.6079 (3)0.0814 (10)
H7A0.48440.87780.57390.13 (2)*
C10.8204 (3)0.5457 (3)0.7304 (3)0.0364 (9)
C20.9552 (3)0.5625 (3)0.7936 (3)0.0389 (9)
C31.0315 (3)0.6062 (3)0.7172 (3)0.0379 (9)
C41.1610 (3)0.6293 (3)0.7192 (3)0.0472 (10)
H41.21800.61850.77510.057*
C51.2039 (3)0.6687 (3)0.6363 (3)0.0512 (10)
H51.29120.68270.63520.061*
C61.1201 (3)0.6881 (3)0.5545 (3)0.0512 (10)
H61.15220.71660.50090.061*
C70.9901 (3)0.6659 (3)0.5509 (3)0.0472 (10)
H70.93300.67830.49620.057*
C80.9500 (3)0.6242 (3)0.6336 (3)0.0366 (9)
C90.9685 (3)0.6634 (4)0.9207 (3)0.0554 (11)
H9A1.05590.68050.95700.083*
H9B0.91580.63710.96790.083*
H9C0.94220.73570.91650.083*
C100.9965 (3)0.4460 (4)0.7976 (3)0.0540 (11)
H10A0.98080.38200.71840.081*
H10B0.94880.42260.84980.081*
H10C1.08590.46020.82710.081*
C110.7060 (3)0.4932 (3)0.7532 (3)0.0405 (9)
H110.63150.48420.70260.049*
C120.6968 (3)0.4556 (3)0.8419 (3)0.0404 (9)
H120.77080.46950.89470.048*
C130.5844 (3)0.3962 (3)0.8641 (3)0.0362 (9)
C140.5970 (3)0.3717 (3)0.9712 (3)0.0414 (9)
C150.4797 (3)0.3160 (3)0.9912 (3)0.0385 (9)
C160.3694 (3)0.2810 (3)0.9127 (3)0.0431 (9)
H160.29750.24220.92760.052*
C170.3660 (3)0.3040 (3)0.8115 (3)0.0410 (9)
C180.4711 (3)0.3609 (3)0.7871 (3)0.0420 (9)
H180.46580.37580.71810.050*
C190.7122 (3)0.6029 (3)0.5736 (3)0.0416 (9)
H19A0.63780.54810.57010.050*
H19B0.73030.58370.49250.050*
C200.6863 (3)0.7329 (4)0.6300 (3)0.0477 (10)
H20A0.67900.75460.71400.057*
H20B0.75750.78640.62530.057*
C210.5665 (4)0.7510 (4)0.5692 (4)0.0476 (10)
N40.2270 (4)0.9048 (3)0.3555 (3)0.0706 (10)
O80.3476 (3)0.9147 (3)0.5204 (3)0.0905 (11)
C220.3295 (5)0.8881 (4)0.4114 (5)0.0765 (14)
H220.39270.85410.36630.092*
C230.1288 (4)0.9612 (5)0.4212 (5)0.0954 (17)
H23A0.05680.90080.40720.143*
H23B0.10321.02200.39510.143*
H23C0.16060.99870.50520.143*
C240.2151 (6)0.8772 (5)0.2293 (4)0.121 (2)
H24A0.29230.85080.19930.182*
H24B0.20030.94880.21670.182*
H24C0.14490.81380.18770.182*
N50.2212 (5)0.0388 (4)0.8664 (4)0.0890 (13)
O90.0087 (5)0.0516 (5)0.8162 (5)0.165 (2)
C250.1183 (8)0.0401 (6)0.7972 (6)0.116 (2)
H25A0.13080.03130.72670.139*
C260.2126 (6)0.0534 (5)0.9757 (5)0.132 (2)
H26A0.27750.00311.03710.198*
H26B0.22430.13500.96380.198*
H26C0.13010.03810.99950.198*
C270.3447 (5)0.0362 (5)0.8282 (5)0.1145 (19)
H27A0.37590.11190.81500.172*
H27B0.40250.02940.88900.172*
H27C0.33830.02440.75510.172*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
N10.0326 (16)0.0457 (19)0.0351 (17)0.0009 (14)0.0004 (13)0.0226 (15)
N20.053 (2)0.063 (3)0.053 (2)0.0008 (19)0.0098 (19)0.027 (2)
N30.041 (2)0.066 (2)0.069 (2)0.0021 (18)0.0018 (18)0.040 (2)
O10.0425 (16)0.106 (2)0.0542 (17)0.0048 (16)0.0036 (14)0.0500 (17)
O20.0542 (18)0.125 (3)0.0583 (19)0.0016 (19)0.0006 (16)0.053 (2)
O30.142 (3)0.103 (3)0.062 (2)0.055 (2)0.006 (2)0.043 (2)
O40.0427 (17)0.103 (3)0.105 (2)0.0154 (17)0.0062 (16)0.066 (2)
O50.0521 (18)0.119 (3)0.078 (2)0.0103 (17)0.0164 (16)0.063 (2)
O60.0483 (17)0.072 (2)0.0618 (18)0.0047 (16)0.0110 (14)0.0276 (16)
O70.063 (2)0.067 (2)0.114 (3)0.0167 (17)0.0133 (18)0.040 (2)
C10.032 (2)0.045 (2)0.035 (2)0.0027 (17)0.0018 (16)0.0204 (18)
C20.033 (2)0.052 (2)0.036 (2)0.0007 (18)0.0010 (16)0.0241 (19)
C30.033 (2)0.045 (2)0.036 (2)0.0008 (18)0.0009 (17)0.0178 (18)
C40.033 (2)0.064 (3)0.045 (2)0.0006 (19)0.0024 (18)0.026 (2)
C50.038 (2)0.062 (3)0.048 (2)0.000 (2)0.0087 (19)0.018 (2)
C60.051 (3)0.059 (3)0.047 (2)0.004 (2)0.012 (2)0.026 (2)
C70.044 (2)0.057 (3)0.044 (2)0.001 (2)0.0007 (19)0.027 (2)
C80.033 (2)0.040 (2)0.039 (2)0.0018 (17)0.0058 (17)0.0194 (18)
C90.049 (2)0.073 (3)0.040 (2)0.006 (2)0.0004 (19)0.023 (2)
C100.042 (2)0.074 (3)0.060 (3)0.007 (2)0.001 (2)0.043 (2)
C110.030 (2)0.052 (2)0.042 (2)0.0040 (18)0.0013 (17)0.024 (2)
C120.034 (2)0.053 (3)0.038 (2)0.0024 (18)0.0001 (17)0.025 (2)
C130.033 (2)0.040 (2)0.038 (2)0.0016 (17)0.0033 (17)0.0197 (18)
C140.040 (2)0.046 (2)0.042 (2)0.0023 (19)0.0019 (18)0.0239 (19)
C150.043 (2)0.045 (2)0.035 (2)0.0045 (19)0.0087 (18)0.0229 (19)
C160.037 (2)0.041 (2)0.053 (2)0.0013 (18)0.0104 (19)0.021 (2)
C170.035 (2)0.047 (2)0.043 (2)0.0004 (18)0.0020 (18)0.024 (2)
C180.042 (2)0.050 (2)0.043 (2)0.0035 (19)0.0053 (18)0.028 (2)
C190.036 (2)0.053 (3)0.040 (2)0.0028 (18)0.0071 (17)0.028 (2)
C200.045 (2)0.058 (3)0.042 (2)0.006 (2)0.0016 (18)0.023 (2)
C210.041 (2)0.063 (3)0.047 (3)0.006 (2)0.006 (2)0.031 (2)
N40.071 (3)0.063 (3)0.077 (3)0.016 (2)0.001 (2)0.028 (2)
O80.076 (2)0.120 (3)0.098 (3)0.033 (2)0.007 (2)0.065 (2)
C220.074 (3)0.078 (4)0.088 (4)0.023 (3)0.018 (3)0.041 (3)
C230.068 (3)0.115 (5)0.108 (4)0.024 (3)0.004 (3)0.049 (4)
C240.173 (6)0.114 (5)0.068 (3)0.044 (4)0.001 (4)0.026 (3)
N50.116 (4)0.071 (3)0.078 (3)0.006 (3)0.016 (3)0.029 (2)
O90.136 (4)0.180 (5)0.177 (5)0.054 (4)0.030 (4)0.059 (4)
C250.147 (5)0.096 (5)0.111 (5)0.044 (5)0.026 (5)0.040 (4)
C260.184 (6)0.117 (5)0.082 (4)0.037 (5)0.010 (4)0.043 (4)
C270.131 (5)0.082 (4)0.117 (5)0.008 (4)0.034 (4)0.025 (4)
Geometric parameters (Å, º) top
N1—C11.322 (4)C12—H120.9300
N1—C81.430 (4)C13—C181.381 (4)
N1—C191.473 (4)C13—C141.454 (4)
N2—O31.213 (4)C14—C151.449 (4)
N2—O21.218 (4)C15—C161.366 (4)
N2—C151.447 (4)C16—C171.373 (4)
N3—O41.223 (4)C16—H160.9300
N3—O51.229 (4)C17—C181.375 (4)
N3—C171.443 (4)C18—H180.9300
O1—C141.238 (4)C19—C201.509 (5)
O6—C211.196 (4)C19—H19A0.9700
O7—C211.312 (5)C19—H19B0.9700
O7—H7A0.8536C20—C211.495 (5)
C1—C111.421 (4)C20—H20A0.9700
C1—C21.522 (4)C20—H20B0.9700
C2—C31.505 (4)N4—C221.310 (5)
C2—C101.531 (5)N4—C231.433 (5)
C2—C91.537 (5)N4—C241.439 (5)
C3—C41.375 (4)O8—C221.236 (5)
C3—C81.379 (4)C22—H220.9300
C4—C51.376 (5)C23—H23A0.9600
C4—H40.9300C23—H23B0.9600
C5—C61.385 (5)C23—H23C0.9600
C5—H50.9300C24—H24A0.9600
C6—C71.376 (4)C24—H24B0.9600
C6—H60.9300C24—H24C0.9600
C7—C81.380 (4)N5—C251.318 (7)
C7—H70.9300N5—C261.428 (6)
C9—H9A0.9600N5—C271.435 (6)
C9—H9B0.9600O9—C251.215 (7)
C9—H9C0.9600C25—H25A0.9300
C10—H10A0.9600C26—H26A0.9600
C10—H10B0.9600C26—H26B0.9600
C10—H10C0.9600C26—H26C0.9600
C11—C121.342 (4)C27—H27A0.9600
C11—H110.9300C27—H27B0.9600
C12—C131.439 (4)C27—H27C0.9600
C1—N1—C8111.0 (3)C16—C15—C14123.4 (3)
C1—N1—C19127.7 (3)N2—C15—C14120.6 (3)
C8—N1—C19121.2 (3)C15—C16—C17119.2 (3)
O3—N2—O2121.8 (3)C15—C16—H16120.4
O3—N2—C15118.5 (3)C17—C16—H16120.4
O2—N2—C15119.5 (3)C16—C17—C18121.6 (3)
O4—N3—O5122.1 (3)C16—C17—N3118.8 (3)
O4—N3—C17118.9 (3)C18—C17—N3119.6 (3)
O5—N3—C17119.0 (3)C17—C18—C13120.6 (3)
C21—O7—H7A112.3C17—C18—H18119.7
N1—C1—C11122.3 (3)C13—C18—H18119.7
N1—C1—C2109.8 (3)N1—C19—C20109.2 (3)
C11—C1—C2127.9 (3)N1—C19—H19A109.8
C3—C2—C1101.0 (2)C20—C19—H19A109.8
C3—C2—C10111.6 (3)N1—C19—H19B109.8
C1—C2—C10114.1 (3)C20—C19—H19B109.8
C3—C2—C9109.6 (3)H19A—C19—H19B108.3
C1—C2—C9109.6 (3)C21—C20—C19111.7 (3)
C10—C2—C9110.6 (3)C21—C20—H20A109.3
C4—C3—C8119.2 (3)C19—C20—H20A109.3
C4—C3—C2131.3 (3)C21—C20—H20B109.3
C8—C3—C2109.5 (3)C19—C20—H20B109.3
C3—C4—C5118.2 (3)H20A—C20—H20B107.9
C3—C4—H4120.9O6—C21—O7123.5 (4)
C5—C4—H4120.9O6—C21—C20124.9 (4)
C4—C5—C6121.5 (3)O7—C21—C20111.5 (4)
C4—C5—H5119.3C22—N4—C23120.3 (4)
C6—C5—H5119.3C22—N4—C24121.1 (4)
C7—C6—C5121.3 (3)C23—N4—C24118.4 (4)
C7—C6—H6119.3O8—C22—N4124.2 (5)
C5—C6—H6119.3O8—C22—H22117.9
C6—C7—C8115.9 (3)N4—C22—H22117.9
C6—C7—H7122.1N4—C23—H23A109.5
C8—C7—H7122.1N4—C23—H23B109.5
C3—C8—C7123.9 (3)H23A—C23—H23B109.5
C3—C8—N1108.2 (3)N4—C23—H23C109.5
C7—C8—N1127.9 (3)H23A—C23—H23C109.5
C2—C9—H9A109.5H23B—C23—H23C109.5
C2—C9—H9B109.5N4—C24—H24A109.5
H9A—C9—H9B109.5N4—C24—H24B109.5
C2—C9—H9C109.5H24A—C24—H24B109.5
H9A—C9—H9C109.5N4—C24—H24C109.5
H9B—C9—H9C109.5H24A—C24—H24C109.5
C2—C10—H10A109.5H24B—C24—H24C109.5
C2—C10—H10B109.5C25—N5—C26121.3 (5)
H10A—C10—H10B109.5C25—N5—C27121.0 (5)
C2—C10—H10C109.5C26—N5—C27117.4 (5)
H10A—C10—H10C109.5O9—C25—N5126.5 (7)
H10B—C10—H10C109.5O9—C25—H25A116.8
C12—C11—C1125.1 (3)N5—C25—H25A116.8
C12—C11—H11117.4N5—C26—H26A109.5
C1—C11—H11117.4N5—C26—H26B109.5
C11—C12—C13126.9 (3)H26A—C26—H26B109.5
C11—C12—H12116.6N5—C26—H26C109.5
C13—C12—H12116.6H26A—C26—H26C109.5
C18—C13—C12122.5 (3)H26B—C26—H26C109.5
C18—C13—C14121.1 (3)N5—C27—H27A109.5
C12—C13—C14116.3 (3)N5—C27—H27B109.5
O1—C14—C15124.1 (3)H27A—C27—H27B109.5
O1—C14—C13122.0 (3)N5—C27—H27C109.5
C15—C14—C13113.9 (3)H27A—C27—H27C109.5
C16—C15—N2116.0 (3)H27B—C27—H27C109.5
C8—N1—C1—C11174.4 (3)C11—C12—C13—C14176.0 (4)
C19—N1—C1—C119.0 (5)C18—C13—C14—O1175.1 (3)
C8—N1—C1—C25.0 (4)C12—C13—C14—O13.4 (5)
C19—N1—C1—C2171.6 (3)C18—C13—C14—C153.8 (5)
N1—C1—C2—C36.7 (4)C12—C13—C14—C15177.8 (3)
C11—C1—C2—C3172.7 (3)O3—N2—C15—C1621.2 (5)
N1—C1—C2—C10126.5 (3)O2—N2—C15—C16153.6 (3)
C11—C1—C2—C1052.8 (5)O3—N2—C15—C14158.6 (4)
N1—C1—C2—C9108.9 (3)O2—N2—C15—C1426.6 (5)
C11—C1—C2—C971.7 (4)O1—C14—C15—C16174.2 (3)
C1—C2—C3—C4174.2 (4)C13—C14—C15—C164.6 (5)
C10—C2—C3—C452.5 (5)O1—C14—C15—N25.6 (6)
C9—C2—C3—C470.3 (5)C13—C14—C15—N2175.6 (3)
C1—C2—C3—C86.0 (4)N2—C15—C16—C17177.2 (3)
C10—C2—C3—C8127.7 (3)C14—C15—C16—C173.0 (5)
C9—C2—C3—C8109.5 (3)C15—C16—C17—C180.2 (5)
C8—C3—C4—C50.5 (5)C15—C16—C17—N3179.9 (3)
C2—C3—C4—C5179.7 (4)O4—N3—C17—C160.4 (5)
C3—C4—C5—C61.6 (6)O5—N3—C17—C16179.7 (4)
C4—C5—C6—C71.5 (6)O4—N3—C17—C18179.9 (4)
C5—C6—C7—C80.2 (5)O5—N3—C17—C180.0 (5)
C4—C3—C8—C70.8 (6)C16—C17—C18—C130.5 (5)
C2—C3—C8—C7179.0 (3)N3—C17—C18—C13179.2 (3)
C4—C3—C8—N1176.6 (3)C12—C13—C18—C17179.8 (3)
C2—C3—C8—N13.6 (4)C14—C13—C18—C171.5 (5)
C6—C7—C8—C30.9 (6)C1—N1—C19—C2095.8 (4)
C6—C7—C8—N1175.9 (3)C8—N1—C19—C2080.5 (4)
C1—N1—C8—C31.0 (4)N1—C19—C20—C21173.4 (3)
C19—N1—C8—C3175.9 (3)C19—C20—C21—O69.3 (5)
C1—N1—C8—C7176.3 (4)C19—C20—C21—O7171.8 (3)
C19—N1—C8—C76.8 (5)C23—N4—C22—O82.5 (7)
N1—C1—C11—C12176.2 (3)C24—N4—C22—O8176.8 (5)
C2—C1—C11—C124.6 (6)C26—N5—C25—O90.9 (10)
C1—C11—C12—C13176.4 (3)C27—N5—C25—O9174.0 (7)
C11—C12—C13—C185.6 (6)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
O7—H7A···O80.851.712.560 (5)173
C4—H4···O1i0.932.463.348 (5)159
C4—H4···O2i0.932.473.175 (5)133
C20—H20A···O3ii0.972.403.345 (5)166
C7—H7···O5iii0.932.583.501 (5)173
C11—H11···O6iii0.932.553.305 (4)139
C18—H18···O6iii0.932.553.401 (4)152
C26—H26A···O30.962.543.319 (8)138
Symmetry codes: (i) x+2, y+1, z+2; (ii) x+1, y+1, z+2; (iii) x+1, y+1, z+1.
 

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