Literature DB >> 24427003

2-(4-Bromo-benzo-yl)-1-ferrocenyl-spiro-[11H-pyrrolidizine-3,11'-indeno-[1,2-b]quinoxaline].

Sivasubramanian Suhitha1, Krishnaswamy Gunasekaran1, Adukamparai Rajukrishnan Sureshbabu2, Raghavachary Raghunathan2, Devadasan Velmurugan1.   

Abstract

In the title compound, [Fe(C5H5)(C33H25BrN3O)], the fused four-ring system, 11H-indeno-[1,2-b]quinoxaline is essentially planar, with a maximum deviation of 0.087 (3) Å from the least-squares plane of the attached benzene ring. The pyrrolidine rings adopt envelope conformation and make a dihedral angle of 51.76 (19)° with each other. The cyclopentadiene rings of the ferrocenyl moiety have an eclipsed conformation. The Br atom deviates by 0.0190 (9) Å from the attached benzene ring. The mol-ecular structure features an intra-molecular C-H⋯N inter-action, which generates an S(8) ring motif. The crystal packing features C-H⋯O inter-actions, which generate R 2 (2)(18) centrosymmetric dimers, as well as C-H⋯π inter-actions.

Entities:  

Year:  2013        PMID： 24427003      PMCID： PMC3884418          DOI： 10.1107/S1600536813023064

Source DB:  PubMed          Journal:  Acta Crystallogr Sect E Struct Rep Online        ISSN： 1600-5368


Related literature

For the biological activity of ferrocene derivatives, see: Jaouen et al. (2004 ▶); Biot et al. (2004 ▶); Fouda et al. (2007 ▶). For a related structure, see: Vijayakumar et al. (2012 ▶). For graph-set notation, see: Bernstein et al. (1995 ▶).

Experimental

Crystal data

[Fe(C5H5)(C33H25BrN3O)] M = 680.41 Triclinic, a = 9.3668 (3) Å b = 9.9785 (3) Å c = 18.6303 (5) Å α = 89.724 (1)° β = 75.967 (1)° γ = 63.236 (1)° V = 1497.37 (8) Å3 Z = 2 Mo Kα radiation μ = 1.88 mm−1 T = 293 K 0.30 × 0.25 × 0.20 mm

Data collection

Bruker SMART APEXII area-detector diffractometer Absorption correction: multi-scan (SADABS; Bruker, 2008 ▶) T min = 0.603, T max = 0.706 22634 measured reflections 6177 independent reflections 5078 reflections with I > 2σ(I) R int = 0.028

Refinement

R[F 2 > 2σ(F 2)] = 0.053 wR(F 2) = 0.137 S = 1.04 6177 reflections 397 parameters H-atom parameters constrained Δρmax = 1.87 e Å−3 Δρmin = −1.63 e Å−3 Data collection: APEX2 (Bruker, 2008 ▶); cell refinement: SAINT (Bruker, 2008 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: ORTEP-3 for Windows (Farrugia, 2012 ▶); software used to prepare material for publication: SHELXL97 and PLATON (Spek, 2009 ▶). Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S1600536813023064/pv2643sup1.cif Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536813023064/pv2643Isup2.hkl Additional supplementary materials: crystallographic information; 3D view; checkCIF report
[Fe(C5H5)(C33H25BrN3O)]Z = 2
Mr = 680.41F(000) = 696
Triclinic, P1Dx = 1.509 Mg m−3
Hall symbol: -P 1Mo Kα radiation, λ = 0.71073 Å
a = 9.3668 (3) ÅCell parameters from 6177 reflections
b = 9.9785 (3) Åθ = 1.1–26.5°
c = 18.6303 (5) ŵ = 1.88 mm−1
α = 89.724 (1)°T = 293 K
β = 75.967 (1)°Block, colourless
γ = 63.236 (1)°0.30 × 0.25 × 0.20 mm
V = 1497.37 (8) Å3
Bruker SMART APEXII area-detector diffractometer6177 independent reflections
Radiation source: fine-focus sealed tube5078 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.028
ω and φ scansθmax = 26.5°, θmin = 1.1°
Absorption correction: multi-scan (SADABS; Bruker, 2008)h = −10→11
Tmin = 0.603, Tmax = 0.706k = −12→12
22634 measured reflectionsl = −23→22
Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.053Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.137H-atom parameters constrained
S = 1.04w = 1/[σ2(Fo2) + (0.0539P)2 + 2.514P] where P = (Fo2 + 2Fc2)/3
6177 reflections(Δ/σ)max = 0.001
397 parametersΔρmax = 1.87 e Å−3
0 restraintsΔρmin = −1.63 e Å−3
Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds 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 > 2sigma(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.
xyzUiso*/Ueq
C10.8769 (4)0.1667 (4)0.66122 (18)0.0415 (7)
C21.0270 (5)0.1122 (5)0.6044 (2)0.0648 (11)
H21.12660.04610.61410.078*
C31.0257 (6)0.1565 (6)0.5353 (3)0.0797 (14)
H31.12500.12020.49800.096*
C40.8782 (6)0.2554 (6)0.5196 (2)0.0740 (13)
H40.87990.28390.47190.089*
C50.7313 (5)0.3108 (5)0.5734 (2)0.0557 (10)
H50.63320.37620.56220.067*
C60.7274 (4)0.2693 (4)0.64563 (17)0.0386 (7)
C70.5854 (4)0.2820 (3)0.76391 (15)0.0304 (6)
C80.4385 (3)0.3328 (3)0.83310 (15)0.0295 (6)
C90.5232 (4)0.2280 (3)0.88732 (16)0.0320 (6)
C100.6945 (4)0.1452 (3)0.85599 (16)0.0343 (6)
C110.7351 (4)0.1757 (3)0.77898 (16)0.0328 (6)
C120.7994 (4)0.0525 (4)0.89628 (18)0.0431 (8)
H120.9131−0.00190.87460.052*
C130.7309 (5)0.0429 (4)0.96949 (19)0.0455 (8)
H130.7989−0.01730.99800.055*
C140.5617 (4)0.1226 (4)1.00030 (17)0.0407 (7)
H140.51730.11411.04940.049*
C150.4560 (4)0.2150 (4)0.96023 (17)0.0374 (7)
H150.34210.26720.98190.045*
C160.4140 (4)0.5472 (4)0.91829 (19)0.0408 (7)
H16A0.44450.62680.90530.049*
H16B0.50580.46400.93110.049*
C170.2585 (4)0.6056 (4)0.98274 (18)0.0450 (8)
H17A0.25030.52381.00870.054*
H17B0.25520.67901.01790.054*
C180.1230 (4)0.6781 (4)0.94348 (18)0.0430 (7)
H18A0.10280.78040.93530.052*
H18B0.02040.68060.97240.052*
C190.1898 (4)0.5771 (3)0.86938 (16)0.0326 (6)
H190.16200.64050.82950.039*
C200.1343 (3)0.4550 (3)0.86635 (16)0.0317 (6)
H200.11340.42420.91620.038*
C210.2879 (3)0.3238 (3)0.81511 (15)0.0302 (6)
H210.28990.34560.76360.036*
C220.2901 (4)0.1712 (4)0.82134 (18)0.0391 (7)
C230.3566 (4)0.0614 (4)0.7524 (2)0.0424 (7)
C240.3524 (5)−0.0764 (4)0.7587 (3)0.0576 (10)
H240.3103−0.09890.80510.069*
C250.4111 (6)−0.1799 (5)0.6958 (3)0.0734 (14)
H250.4095−0.27220.70020.088*
C260.4712 (5)−0.1460 (5)0.6274 (3)0.0655 (12)
C270.4777 (5)−0.0127 (5)0.6198 (2)0.0601 (10)
H270.52010.00850.57310.072*
C280.4208 (4)0.0906 (4)0.6822 (2)0.0484 (8)
H280.42550.18140.67700.058*
C290.0989 (6)0.4878 (5)0.6368 (2)0.0650 (11)
H290.16030.37930.61940.078*
C30−0.0631 (6)0.5873 (7)0.6318 (2)0.0728 (14)
H30−0.13340.56050.61000.087*
C31−0.1036 (5)0.7318 (6)0.6630 (2)0.0672 (13)
H31−0.20810.82370.66720.081*
C320.0316 (5)0.7225 (5)0.6868 (2)0.0536 (9)
H320.03730.80640.71080.064*
C330.1567 (4)0.5718 (5)0.6704 (2)0.0511 (9)
H330.26480.53210.68120.061*
C34−0.1484 (4)0.6599 (4)0.85115 (17)0.0405 (7)
H34−0.14910.74730.87540.049*
C35−0.2744 (4)0.6630 (5)0.82032 (19)0.0484 (8)
H35−0.37760.75290.82010.058*
C36−0.2267 (4)0.5159 (5)0.7909 (2)0.0518 (9)
H36−0.29040.48510.76620.062*
C37−0.0698 (4)0.4184 (4)0.80284 (19)0.0435 (8)
H37−0.00610.30930.78730.052*
C38−0.0201 (4)0.5077 (4)0.84020 (16)0.0348 (6)
N10.8802 (3)0.1180 (3)0.73019 (15)0.0420 (6)
N20.5773 (3)0.3290 (3)0.69911 (14)0.0356 (6)
N30.3720 (3)0.4961 (3)0.85602 (13)0.0321 (5)
O10.2360 (4)0.1392 (3)0.88107 (15)0.0613 (7)
Fe1−0.05693 (5)0.58417 (5)0.74004 (2)0.03596 (14)
Br10.54872 (10)−0.28490 (7)0.54137 (4)0.1181 (3)
U11U22U33U12U13U23
C10.0385 (17)0.0447 (18)0.0328 (16)−0.0166 (14)−0.0003 (13)0.0003 (13)
C20.041 (2)0.077 (3)0.052 (2)−0.014 (2)0.0034 (17)0.004 (2)
C30.059 (3)0.103 (4)0.049 (2)−0.028 (3)0.015 (2)0.006 (2)
C40.077 (3)0.099 (4)0.037 (2)−0.040 (3)0.001 (2)0.017 (2)
C50.056 (2)0.073 (3)0.0352 (18)−0.029 (2)−0.0085 (16)0.0162 (17)
C60.0418 (17)0.0453 (18)0.0287 (15)−0.0228 (15)−0.0043 (13)0.0044 (13)
C70.0322 (14)0.0306 (14)0.0272 (14)−0.0135 (12)−0.0080 (11)0.0044 (11)
C80.0308 (14)0.0293 (14)0.0249 (13)−0.0113 (12)−0.0067 (11)0.0045 (11)
C90.0375 (15)0.0304 (14)0.0270 (14)−0.0139 (12)−0.0104 (12)0.0049 (11)
C100.0399 (16)0.0298 (15)0.0304 (15)−0.0128 (13)−0.0114 (12)0.0050 (12)
C110.0326 (15)0.0297 (14)0.0319 (15)−0.0106 (12)−0.0094 (12)0.0022 (11)
C120.0425 (18)0.0355 (16)0.0420 (18)−0.0073 (14)−0.0169 (14)0.0071 (14)
C130.059 (2)0.0363 (17)0.0393 (18)−0.0154 (16)−0.0246 (16)0.0129 (14)
C140.062 (2)0.0381 (17)0.0266 (15)−0.0257 (16)−0.0135 (14)0.0096 (12)
C150.0429 (17)0.0361 (16)0.0315 (15)−0.0179 (14)−0.0079 (13)0.0061 (12)
C160.0357 (16)0.0385 (17)0.0493 (19)−0.0153 (14)−0.0170 (14)−0.0033 (14)
C170.054 (2)0.0453 (19)0.0358 (17)−0.0209 (16)−0.0158 (15)−0.0010 (14)
C180.0345 (16)0.0441 (18)0.0411 (18)−0.0117 (14)−0.0070 (13)−0.0095 (14)
C190.0312 (14)0.0317 (15)0.0320 (15)−0.0105 (12)−0.0119 (12)0.0032 (12)
C200.0309 (14)0.0382 (15)0.0250 (14)−0.0153 (13)−0.0069 (11)0.0055 (11)
C210.0333 (14)0.0333 (15)0.0249 (13)−0.0154 (12)−0.0094 (11)0.0052 (11)
C220.0422 (17)0.0375 (16)0.0422 (18)−0.0194 (14)−0.0175 (14)0.0110 (14)
C230.0390 (17)0.0322 (16)0.059 (2)−0.0137 (14)−0.0234 (15)0.0039 (14)
C240.060 (2)0.0398 (19)0.082 (3)−0.0240 (18)−0.033 (2)0.0107 (19)
C250.075 (3)0.035 (2)0.119 (4)−0.022 (2)−0.049 (3)−0.002 (2)
C260.058 (2)0.045 (2)0.084 (3)−0.0070 (19)−0.035 (2)−0.018 (2)
C270.057 (2)0.053 (2)0.062 (2)−0.0159 (19)−0.0194 (19)−0.0120 (18)
C280.050 (2)0.0398 (18)0.053 (2)−0.0180 (16)−0.0156 (16)−0.0040 (15)
C290.071 (3)0.074 (3)0.0335 (19)−0.028 (2)0.0031 (18)−0.0028 (18)
C300.074 (3)0.123 (4)0.036 (2)−0.053 (3)−0.025 (2)0.017 (2)
C310.048 (2)0.087 (3)0.052 (2)−0.017 (2)−0.0178 (18)0.035 (2)
C320.055 (2)0.059 (2)0.048 (2)−0.0292 (19)−0.0099 (17)0.0200 (17)
C330.0373 (17)0.070 (2)0.0415 (19)−0.0228 (18)−0.0069 (14)0.0207 (17)
C340.0303 (15)0.0507 (19)0.0332 (16)−0.0146 (14)−0.0045 (12)0.0004 (14)
C350.0277 (15)0.068 (2)0.0429 (18)−0.0174 (16)−0.0082 (13)0.0077 (17)
C360.0408 (18)0.076 (3)0.054 (2)−0.0379 (19)−0.0158 (16)0.0109 (19)
C370.0438 (18)0.051 (2)0.0462 (19)−0.0301 (16)−0.0140 (15)0.0101 (15)
C380.0308 (14)0.0470 (18)0.0276 (14)−0.0203 (13)−0.0054 (11)0.0063 (12)
N10.0332 (13)0.0411 (15)0.0395 (15)−0.0088 (12)−0.0056 (11)0.0018 (12)
N20.0357 (13)0.0417 (14)0.0285 (13)−0.0173 (11)−0.0084 (10)0.0072 (11)
N30.0302 (12)0.0313 (12)0.0325 (13)−0.0122 (10)−0.0085 (10)0.0023 (10)
O10.094 (2)0.0613 (17)0.0467 (15)−0.0507 (16)−0.0196 (14)0.0214 (13)
Fe10.0312 (2)0.0472 (3)0.0305 (2)−0.0182 (2)−0.00988 (17)0.00543 (18)
Br10.1451 (6)0.0685 (4)0.1205 (5)−0.0226 (4)−0.0544 (5)−0.0415 (3)
C1—N11.374 (4)C20—H200.9800
C1—C21.410 (5)C21—C221.518 (4)
C1—C61.414 (5)C21—H210.9800
C2—C31.360 (6)C22—O11.211 (4)
C2—H20.9300C22—C231.499 (5)
C3—C41.391 (7)C23—C281.390 (5)
C3—H30.9300C23—C241.397 (5)
C4—C51.362 (6)C24—C251.390 (6)
C4—H40.9300C24—H240.9300
C5—C61.403 (5)C25—C261.369 (7)
C5—H50.9300C25—H250.9300
C6—N21.377 (4)C26—C271.364 (6)
C7—N21.300 (4)C26—Br11.889 (4)
C7—C111.421 (4)C27—C281.383 (5)
C7—C81.526 (4)C27—H270.9300
C8—N31.480 (4)C28—H280.9300
C8—C91.541 (4)C29—C331.403 (6)
C8—C211.566 (4)C29—C301.417 (7)
C9—C151.384 (4)C29—Fe12.037 (4)
C9—C101.398 (4)C29—H290.9800
C10—C121.385 (4)C30—C311.403 (7)
C10—C111.460 (4)C30—Fe12.031 (4)
C11—N11.306 (4)C30—H300.9800
C12—C131.383 (5)C31—C321.406 (6)
C12—H120.9300C31—Fe12.031 (4)
C13—C141.379 (5)C31—H310.9800
C13—H130.9300C32—C331.404 (6)
C14—C151.385 (4)C32—Fe12.048 (4)
C14—H140.9300C32—H320.9800
C15—H150.9300C33—Fe12.054 (3)
C16—N31.472 (4)C33—H330.9800
C16—C171.515 (5)C34—C351.422 (5)
C16—H16A0.9700C34—C381.426 (5)
C16—H16B0.9700C34—Fe12.040 (3)
C17—C181.513 (5)C34—H340.9800
C17—H17A0.9700C35—C361.398 (6)
C17—H17B0.9700C35—Fe12.024 (3)
C18—C191.529 (4)C35—H350.9800
C18—H18A0.9700C36—C371.423 (5)
C18—H18B0.9700C36—Fe12.032 (3)
C19—N31.477 (4)C36—H360.9800
C19—C201.530 (4)C37—C381.425 (4)
C19—H190.9800C37—Fe12.052 (3)
C20—C381.503 (4)C37—H370.9800
C20—C211.531 (4)C38—Fe12.060 (3)
N1—C1—C2119.0 (3)C33—C29—H29125.9
N1—C1—C6121.8 (3)C30—C29—H29125.9
C2—C1—C6119.2 (3)Fe1—C29—H29125.9
C3—C2—C1119.8 (4)C31—C30—C29107.4 (4)
C3—C2—H2120.1C31—C30—Fe169.8 (2)
C1—C2—H2120.1C29—C30—Fe169.8 (2)
C2—C3—C4121.1 (4)C31—C30—H30126.3
C2—C3—H3119.5C29—C30—H30126.3
C4—C3—H3119.5Fe1—C30—H30126.3
C5—C4—C3120.5 (4)C30—C31—C32108.4 (4)
C5—C4—H4119.7C30—C31—Fe169.8 (2)
C3—C4—H4119.7C32—C31—Fe170.5 (2)
C4—C5—C6120.2 (4)C30—C31—H31125.8
C4—C5—H5119.9C32—C31—H31125.8
C6—C5—H5119.9Fe1—C31—H31125.8
N2—C6—C5118.9 (3)C33—C32—C31108.0 (4)
N2—C6—C1122.0 (3)C33—C32—Fe170.2 (2)
C5—C6—C1119.2 (3)C31—C32—Fe169.2 (2)
N2—C7—C11123.5 (3)C33—C32—H32126.0
N2—C7—C8125.2 (3)C31—C32—H32126.0
C11—C7—C8111.3 (2)Fe1—C32—H32126.0
N3—C8—C7109.5 (2)C29—C33—C32108.0 (4)
N3—C8—C9114.8 (2)C29—C33—Fe169.3 (2)
C7—C8—C9100.2 (2)C32—C33—Fe169.7 (2)
N3—C8—C21103.0 (2)C29—C33—H33126.0
C7—C8—C21111.2 (2)C32—C33—H33126.0
C9—C8—C21118.2 (2)Fe1—C33—H33126.0
C15—C9—C10119.1 (3)C35—C34—C38108.1 (3)
C15—C9—C8129.6 (3)C35—C34—Fe168.91 (19)
C10—C9—C8111.1 (2)C38—C34—Fe170.42 (17)
C12—C10—C9121.9 (3)C35—C34—H34126.0
C12—C10—C11129.0 (3)C38—C34—H34126.0
C9—C10—C11109.1 (2)Fe1—C34—H34126.0
N1—C11—C7123.9 (3)C36—C35—C34108.4 (3)
N1—C11—C10128.2 (3)C36—C35—Fe170.2 (2)
C7—C11—C10107.9 (2)C34—C35—Fe170.14 (18)
C13—C12—C10118.3 (3)C36—C35—H35125.8
C13—C12—H12120.8C34—C35—H35125.8
C10—C12—H12120.8Fe1—C35—H35125.8
C14—C13—C12120.0 (3)C35—C36—C37108.3 (3)
C14—C13—H13120.0C35—C36—Fe169.5 (2)
C12—C13—H13120.0C37—C36—Fe170.37 (18)
C13—C14—C15122.0 (3)C35—C36—H36125.8
C13—C14—H14119.0C37—C36—H36125.8
C15—C14—H14119.0Fe1—C36—H36125.8
C9—C15—C14118.7 (3)C36—C37—C38108.1 (3)
C9—C15—H15120.7C36—C37—Fe168.9 (2)
C14—C15—H15120.7C38—C37—Fe170.04 (18)
N3—C16—C17105.6 (2)C36—C37—H37125.9
N3—C16—H16A110.6C38—C37—H37125.9
C17—C16—H16A110.6Fe1—C37—H37125.9
N3—C16—H16B110.6C37—C38—C34107.1 (3)
C17—C16—H16B110.6C37—C38—C20127.8 (3)
H16A—C16—H16B108.8C34—C38—C20125.0 (3)
C18—C17—C16102.0 (3)C37—C38—Fe169.41 (18)
C18—C17—H17A111.4C34—C38—Fe168.89 (17)
C16—C17—H17A111.4C20—C38—Fe1128.3 (2)
C18—C17—H17B111.4C11—N1—C1114.2 (3)
C16—C17—H17B111.4C7—N2—C6114.5 (3)
H17A—C17—H17B109.2C16—N3—C19108.0 (2)
C17—C18—C19104.5 (3)C16—N3—C8120.4 (2)
C17—C18—H18A110.9C19—N3—C8111.3 (2)
C19—C18—H18A110.9C35—Fe1—C31104.76 (16)
C17—C18—H18B110.9C35—Fe1—C30118.40 (17)
C19—C18—H18B110.9C31—Fe1—C3040.4 (2)
H18A—C18—H18B108.9C35—Fe1—C3640.32 (16)
N3—C19—C18106.0 (2)C31—Fe1—C36120.97 (17)
N3—C19—C20106.1 (2)C30—Fe1—C36105.07 (17)
C18—C19—C20116.5 (3)C35—Fe1—C29155.23 (17)
N3—C19—H19109.3C31—Fe1—C2967.95 (19)
C18—C19—H19109.3C30—Fe1—C2940.78 (19)
C20—C19—H19109.3C36—Fe1—C29121.61 (18)
C38—C20—C19112.8 (2)C35—Fe1—C3440.95 (13)
C38—C20—C21114.2 (2)C31—Fe1—C34120.64 (18)
C19—C20—C21102.9 (2)C30—Fe1—C34154.82 (18)
C38—C20—H20108.9C36—Fe1—C3468.33 (15)
C19—C20—H20108.9C29—Fe1—C34163.11 (16)
C21—C20—H20108.9C35—Fe1—C32123.07 (17)
C22—C21—C20114.3 (2)C31—Fe1—C3240.32 (17)
C22—C21—C8114.8 (2)C30—Fe1—C3267.89 (19)
C20—C21—C8104.6 (2)C36—Fe1—C32158.00 (16)
C22—C21—H21107.6C29—Fe1—C3267.54 (18)
C20—C21—H21107.6C34—Fe1—C32108.66 (16)
C8—C21—H21107.6C35—Fe1—C3768.24 (15)
O1—C22—C23120.2 (3)C31—Fe1—C37158.56 (17)
O1—C22—C21120.5 (3)C30—Fe1—C37123.57 (19)
C23—C22—C21119.3 (3)C36—Fe1—C3740.77 (14)
C28—C23—C24118.2 (3)C29—Fe1—C37109.45 (17)
C28—C23—C22123.2 (3)C34—Fe1—C3768.17 (14)
C24—C23—C22118.6 (3)C32—Fe1—C37160.23 (15)
C25—C24—C23120.1 (4)C35—Fe1—C33160.93 (17)
C25—C24—H24120.0C31—Fe1—C3367.63 (15)
C23—C24—H24120.0C30—Fe1—C3367.94 (17)
C26—C25—C24119.9 (4)C36—Fe1—C33158.65 (17)
C26—C25—H25120.0C29—Fe1—C3340.09 (17)
C24—C25—H25120.0C34—Fe1—C33126.52 (15)
C27—C26—C25121.1 (4)C32—Fe1—C3340.02 (16)
C27—C26—Br1118.6 (4)C37—Fe1—C33125.08 (15)
C25—C26—Br1120.3 (3)C35—Fe1—C3868.70 (13)
C26—C27—C28119.4 (4)C31—Fe1—C38157.77 (19)
C26—C27—H27120.3C30—Fe1—C38161.55 (19)
C28—C27—H27120.3C36—Fe1—C3868.57 (13)
C27—C28—C23121.3 (4)C29—Fe1—C38126.66 (16)
C27—C28—H28119.4C34—Fe1—C3840.69 (13)
C23—C28—H28119.4C32—Fe1—C38124.33 (14)
C33—C29—C30108.1 (4)C37—Fe1—C3840.55 (13)
C33—C29—Fe170.6 (2)C33—Fe1—C38111.35 (13)
C30—C29—Fe169.4 (2)
N1—C1—C2—C3178.6 (4)C30—C31—Fe1—C35−116.7 (3)
C6—C1—C2—C3−1.2 (7)C32—C31—Fe1—C35124.2 (3)
C1—C2—C3—C40.1 (8)C32—C31—Fe1—C30−119.1 (4)
C2—C3—C4—C50.4 (9)C30—C31—Fe1—C36−76.3 (3)
C3—C4—C5—C60.4 (8)C32—C31—Fe1—C36164.6 (2)
C4—C5—C6—N2179.0 (4)C30—C31—Fe1—C2938.3 (3)
C4—C5—C6—C1−1.6 (6)C32—C31—Fe1—C29−80.8 (3)
N1—C1—C6—N21.5 (5)C30—C31—Fe1—C34−157.9 (2)
C2—C1—C6—N2−178.6 (3)C32—C31—Fe1—C3482.9 (3)
N1—C1—C6—C5−177.8 (3)C30—C31—Fe1—C32119.1 (4)
C2—C1—C6—C52.0 (5)C30—C31—Fe1—C37−48.9 (5)
N2—C7—C8—N3−64.2 (4)C32—C31—Fe1—C37−168.0 (4)
C11—C7—C8—N3115.6 (3)C30—C31—Fe1—C3381.8 (3)
N2—C7—C8—C9174.8 (3)C32—C31—Fe1—C33−37.4 (3)
C11—C7—C8—C9−5.5 (3)C30—C31—Fe1—C38173.7 (3)
N2—C7—C8—C2149.0 (4)C32—C31—Fe1—C3854.6 (5)
C11—C7—C8—C21−131.3 (3)C31—C30—Fe1—C3579.1 (3)
N3—C8—C9—C1564.3 (4)C29—C30—Fe1—C35−162.5 (3)
C7—C8—C9—C15−178.5 (3)C29—C30—Fe1—C31118.4 (4)
C21—C8—C9—C15−57.5 (4)C31—C30—Fe1—C36120.4 (3)
N3—C8—C9—C10−110.9 (3)C29—C30—Fe1—C36−121.3 (3)
C7—C8—C9—C106.3 (3)C31—C30—Fe1—C29−118.4 (4)
C21—C8—C9—C10127.2 (3)C31—C30—Fe1—C3449.4 (5)
C15—C9—C10—C12−1.2 (5)C29—C30—Fe1—C34167.8 (3)
C8—C9—C10—C12174.6 (3)C31—C30—Fe1—C32−37.6 (2)
C15—C9—C10—C11179.2 (3)C29—C30—Fe1—C3280.8 (3)
C8—C9—C10—C11−5.0 (3)C31—C30—Fe1—C37160.7 (2)
N2—C7—C11—N12.2 (5)C29—C30—Fe1—C37−80.9 (3)
C8—C7—C11—N1−177.5 (3)C31—C30—Fe1—C33−80.9 (3)
N2—C7—C11—C10−177.3 (3)C29—C30—Fe1—C3337.4 (3)
C8—C7—C11—C102.9 (3)C31—C30—Fe1—C38−172.5 (4)
C12—C10—C11—N12.3 (6)C29—C30—Fe1—C38−54.1 (6)
C9—C10—C11—N1−178.2 (3)C37—C36—Fe1—C35−119.3 (3)
C12—C10—C11—C7−178.2 (3)C35—C36—Fe1—C31−75.6 (3)
C9—C10—C11—C71.3 (3)C37—C36—Fe1—C31165.1 (2)
C9—C10—C12—C130.0 (5)C35—C36—Fe1—C30−116.3 (3)
C11—C10—C12—C13179.5 (3)C37—C36—Fe1—C30124.4 (3)
C10—C12—C13—C141.0 (5)C35—C36—Fe1—C29−157.3 (2)
C12—C13—C14—C15−0.7 (5)C37—C36—Fe1—C2983.4 (3)
C10—C9—C15—C141.5 (5)C35—C36—Fe1—C3438.0 (2)
C8—C9—C15—C14−173.4 (3)C37—C36—Fe1—C34−81.3 (2)
C13—C14—C15—C9−0.5 (5)C35—C36—Fe1—C32−48.3 (5)
N3—C16—C17—C18−36.3 (3)C37—C36—Fe1—C32−167.6 (4)
C16—C17—C18—C1935.3 (3)C35—C36—Fe1—C37119.3 (3)
C17—C18—C19—N3−21.9 (3)C35—C36—Fe1—C33175.9 (4)
C17—C18—C19—C2095.8 (3)C37—C36—Fe1—C3356.7 (5)
N3—C19—C20—C38−150.8 (2)C35—C36—Fe1—C3881.9 (2)
C18—C19—C20—C3891.6 (3)C37—C36—Fe1—C38−37.4 (2)
N3—C19—C20—C21−27.1 (3)C33—C29—Fe1—C35158.2 (4)
C18—C19—C20—C21−144.8 (2)C30—C29—Fe1—C3539.2 (6)
C38—C20—C21—C22−76.1 (3)C33—C29—Fe1—C3181.0 (3)
C19—C20—C21—C22161.2 (2)C30—C29—Fe1—C31−38.0 (3)
C38—C20—C21—C8157.6 (2)C33—C29—Fe1—C30119.0 (4)
C19—C20—C21—C834.9 (3)C33—C29—Fe1—C36−165.3 (2)
N3—C8—C21—C22−155.6 (2)C30—C29—Fe1—C3675.8 (3)
C7—C8—C21—C2287.2 (3)C33—C29—Fe1—C34−43.0 (7)
C9—C8—C21—C22−27.9 (4)C30—C29—Fe1—C34−161.9 (5)
N3—C8—C21—C20−29.5 (3)C33—C29—Fe1—C3237.3 (2)
C7—C8—C21—C20−146.8 (2)C30—C29—Fe1—C32−81.7 (3)
C9—C8—C21—C2098.2 (3)C33—C29—Fe1—C37−121.8 (2)
C20—C21—C22—O1−36.7 (4)C30—C29—Fe1—C37119.2 (3)
C8—C21—C22—O184.2 (4)C30—C29—Fe1—C33−119.0 (4)
C20—C21—C22—C23142.0 (3)C33—C29—Fe1—C38−79.7 (3)
C8—C21—C22—C23−97.1 (3)C30—C29—Fe1—C38161.4 (3)
O1—C22—C23—C28−179.9 (3)C38—C34—Fe1—C35119.3 (3)
C21—C22—C23—C281.4 (5)C35—C34—Fe1—C3176.6 (3)
O1—C22—C23—C240.9 (5)C38—C34—Fe1—C31−164.0 (2)
C21—C22—C23—C24−177.8 (3)C35—C34—Fe1—C3041.7 (5)
C28—C23—C24—C25−0.1 (5)C38—C34—Fe1—C30161.1 (4)
C22—C23—C24—C25179.2 (3)C35—C34—Fe1—C36−37.4 (2)
C23—C24—C25—C26−0.8 (6)C38—C34—Fe1—C3681.9 (2)
C24—C25—C26—C271.3 (7)C35—C34—Fe1—C29−166.7 (6)
C24—C25—C26—Br1−179.2 (3)C38—C34—Fe1—C29−47.3 (6)
C25—C26—C27—C28−0.8 (6)C35—C34—Fe1—C32119.3 (2)
Br1—C26—C27—C28179.7 (3)C38—C34—Fe1—C32−121.3 (2)
C26—C27—C28—C23−0.1 (6)C35—C34—Fe1—C37−81.5 (2)
C24—C23—C28—C270.6 (5)C38—C34—Fe1—C3737.85 (18)
C22—C23—C28—C27−178.7 (3)C35—C34—Fe1—C33160.2 (2)
C33—C29—C30—C31−0.3 (5)C38—C34—Fe1—C33−80.4 (2)
Fe1—C29—C30—C3159.9 (3)C35—C34—Fe1—C38−119.3 (3)
C33—C29—C30—Fe1−60.3 (3)C33—C32—Fe1—C35168.1 (2)
C29—C30—C31—C320.2 (5)C31—C32—Fe1—C35−72.7 (3)
Fe1—C30—C31—C3260.2 (3)C33—C32—Fe1—C31−119.2 (4)
C29—C30—C31—Fe1−60.0 (3)C33—C32—Fe1—C30−81.6 (3)
C30—C31—C32—C330.0 (4)C31—C32—Fe1—C3037.7 (3)
Fe1—C31—C32—C3359.7 (2)C33—C32—Fe1—C36−156.7 (4)
C30—C31—C32—Fe1−59.8 (3)C31—C32—Fe1—C36−37.5 (6)
C30—C29—C33—C320.3 (4)C33—C32—Fe1—C29−37.3 (2)
Fe1—C29—C33—C32−59.2 (2)C31—C32—Fe1—C2981.9 (3)
C30—C29—C33—Fe159.5 (3)C33—C32—Fe1—C34125.1 (2)
C31—C32—C33—C29−0.2 (4)C31—C32—Fe1—C34−115.7 (3)
Fe1—C32—C33—C2958.9 (3)C33—C32—Fe1—C3747.8 (6)
C31—C32—C33—Fe1−59.1 (3)C31—C32—Fe1—C37167.1 (4)
C38—C34—C35—C360.2 (4)C31—C32—Fe1—C33119.2 (4)
Fe1—C34—C35—C3660.0 (2)C33—C32—Fe1—C3882.7 (3)
C38—C34—C35—Fe1−59.8 (2)C31—C32—Fe1—C38−158.1 (3)
C34—C35—C36—C370.0 (4)C36—C37—Fe1—C3537.4 (2)
Fe1—C35—C36—C3759.9 (2)C38—C37—Fe1—C35−82.2 (2)
C34—C35—C36—Fe1−60.0 (2)C36—C37—Fe1—C31−37.1 (5)
C35—C36—C37—C38−0.2 (4)C38—C37—Fe1—C31−156.8 (4)
Fe1—C36—C37—C3859.2 (2)C36—C37—Fe1—C30−73.0 (3)
C35—C36—C37—Fe1−59.4 (2)C38—C37—Fe1—C30167.3 (2)
C36—C37—C38—C340.3 (4)C38—C37—Fe1—C36−119.7 (3)
Fe1—C37—C38—C3458.8 (2)C36—C37—Fe1—C29−116.2 (3)
C36—C37—C38—C20178.4 (3)C38—C37—Fe1—C29124.1 (2)
Fe1—C37—C38—C20−123.1 (3)C36—C37—Fe1—C3481.7 (2)
C36—C37—C38—Fe1−58.5 (2)C38—C37—Fe1—C34−37.98 (18)
C35—C34—C38—C37−0.3 (3)C36—C37—Fe1—C32166.2 (4)
Fe1—C34—C38—C37−59.1 (2)C38—C37—Fe1—C3246.6 (5)
C35—C34—C38—C20−178.5 (3)C36—C37—Fe1—C33−158.2 (2)
Fe1—C34—C38—C20122.7 (3)C38—C37—Fe1—C3382.2 (2)
C35—C34—C38—Fe158.8 (2)C36—C37—Fe1—C38119.7 (3)
C19—C20—C38—C37152.6 (3)C29—C33—Fe1—C35−151.5 (4)
C21—C20—C38—C3735.4 (4)C32—C33—Fe1—C35−32.0 (5)
C19—C20—C38—C34−29.6 (4)C29—C33—Fe1—C31−81.9 (3)
C21—C20—C38—C34−146.8 (3)C32—C33—Fe1—C3137.6 (3)
C19—C20—C38—Fe160.0 (3)C29—C33—Fe1—C30−38.1 (3)
C21—C20—C38—Fe1−57.2 (4)C32—C33—Fe1—C3081.4 (3)
C7—C11—N1—C1−1.2 (5)C29—C33—Fe1—C3636.5 (5)
C10—C11—N1—C1178.2 (3)C32—C33—Fe1—C36156.0 (4)
C2—C1—N1—C11179.6 (3)C32—C33—Fe1—C29119.5 (3)
C6—C1—N1—C11−0.5 (5)C29—C33—Fe1—C34165.7 (2)
C11—C7—N2—C6−1.1 (4)C32—C33—Fe1—C34−74.8 (3)
C8—C7—N2—C6178.6 (3)C29—C33—Fe1—C32−119.5 (3)
C5—C6—N2—C7178.7 (3)C29—C33—Fe1—C3778.3 (3)
C1—C6—N2—C7−0.6 (4)C32—C33—Fe1—C37−162.2 (2)
C17—C16—N3—C1923.4 (3)C29—C33—Fe1—C38122.1 (3)
C17—C16—N3—C8−105.9 (3)C32—C33—Fe1—C38−118.4 (2)
C18—C19—N3—C16−0.9 (3)C37—C38—Fe1—C3581.0 (2)
C20—C19—N3—C16−125.3 (3)C34—C38—Fe1—C35−37.8 (2)
C18—C19—N3—C8133.4 (3)C20—C38—Fe1—C35−156.4 (3)
C20—C19—N3—C88.9 (3)C37—C38—Fe1—C31157.6 (4)
C7—C8—N3—C16−101.0 (3)C34—C38—Fe1—C3138.8 (4)
C9—C8—N3—C1610.7 (4)C20—C38—Fe1—C31−79.8 (5)
C21—C8—N3—C16140.6 (3)C37—C38—Fe1—C30−35.4 (5)
C7—C8—N3—C19131.2 (2)C34—C38—Fe1—C30−154.2 (5)
C9—C8—N3—C19−117.1 (3)C20—C38—Fe1—C3087.2 (6)
C21—C8—N3—C1912.8 (3)C37—C38—Fe1—C3637.6 (2)
C36—C35—Fe1—C31120.8 (3)C34—C38—Fe1—C36−81.3 (2)
C34—C35—Fe1—C31−120.0 (3)C20—C38—Fe1—C36160.1 (3)
C36—C35—Fe1—C3079.6 (3)C37—C38—Fe1—C29−76.6 (3)
C34—C35—Fe1—C30−161.2 (3)C34—C38—Fe1—C29164.6 (2)
C34—C35—Fe1—C36119.2 (3)C20—C38—Fe1—C2945.9 (4)
C36—C35—Fe1—C2951.6 (5)C37—C38—Fe1—C34118.8 (3)
C34—C35—Fe1—C29170.8 (4)C20—C38—Fe1—C34−118.6 (4)
C36—C35—Fe1—C34−119.2 (3)C37—C38—Fe1—C32−162.7 (2)
C36—C35—Fe1—C32160.5 (2)C34—C38—Fe1—C3278.5 (2)
C34—C35—Fe1—C32−80.3 (3)C20—C38—Fe1—C32−40.2 (3)
C36—C35—Fe1—C37−37.8 (2)C34—C38—Fe1—C37−118.8 (3)
C34—C35—Fe1—C3781.3 (2)C20—C38—Fe1—C37122.5 (4)
C36—C35—Fe1—C33−175.5 (4)C37—C38—Fe1—C33−119.5 (2)
C34—C35—Fe1—C33−56.3 (5)C34—C38—Fe1—C33121.7 (2)
C36—C35—Fe1—C38−81.6 (2)C20—C38—Fe1—C333.1 (3)
C34—C35—Fe1—C3837.6 (2)
D—H···AD—HH···AD···AD—H···A
C28—H28···N20.932.563.358 (5)145
C13—H13···O1i0.932.583.318 (4)137
C4—H4···Cg1ii0.932.693.580 (4)159
C17—H17B···Cg2iii0.972.843.743 (4)155
C36—H36···Cg3iv0.982.703.486 (5)137
Table 1

Hydrogen-bond geometry (Å, °)

Cg1, Cg2 and Cg3 are the centroids of the C29–C33, C9–C15 and N1/N2/C1/C6/C7/C11 rings, respectively.

D—H⋯A D—HH⋯A D⋯A D—H⋯A
C28—H28⋯N20.932.563.358 (5)145
C13—H13⋯O1i 0.932.583.318 (4)137
C4—H4⋯Cg1ii 0.932.693.580 (4)159
C17—H17B⋯Cg2iii 0.972.843.743 (4)155
C36—H36⋯Cg3iv 0.982.703.486 (5)137

Symmetry codes: (i) ; (ii) ; (iii) ; (iv) .

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Journal:  Acta Crystallogr A       Date:  2007-12-21       Impact factor: 2.290

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3.  3'-Ferrocenylcarbon-yl-1'-methyl-4'-phenyl-spiro-[indeno-[2,3-b]quinoxaline-11,2'-pyrrolidine].

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Journal:  Acta Crystallogr Sect E Struct Rep Online       Date:  2012-10-20

4.  Structure validation in chemical crystallography.

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Journal:  Acta Crystallogr D Biol Crystallogr       Date:  2009-01-20
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