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Acta Crystallogr Sect E Struct Rep Online. 2010 April 1; 66(Pt 4): o810–o811.
Published online 2010 March 13. doi:  10.1107/S1600536810007804
PMCID: PMC2983798

Methyl 4-(4-chloro­phen­yl)-1,2,3,3a,4,4a,5,12c-octa­hydro­benzo[f]chromeno[3,4-b]pyrrolizine-4a-carboxyl­ate

Abstract

There are two mol­ecules in the asymmetric unit of the title compound, C26H24ClNO3. The dihedral angles between the naphthalene ring system and the chloro­phenyl substituent are 58.76 (9) and 51.59 (8)° in the two mol­ecules. In the pyrrolizine ring system, both the pyrrolidine rings adopt envelope conformations and the dihydro­pyran rings adopt half-chair conformations. In the pyrrolizine ring system of one of the mol­ecules, one of the C atoms is disordered over two positions with site occupancies of 0.69 (2) and 0.31 (2). The crystal packing is stabilized by weak intra­molecular C—H(...)O inter­actions and the crystal packing is stabilized by weak C—H(...)π inter­actions.

Related literature

For the biological activity of chromenopyrroles, see: Caine (1993 [triangle]); Tidey (1992 [triangle]); Carlson (1993 [triangle]); Sokoloff et al. (1990 [triangle]); Wilner (1985 [triangle]). For a related structure, see: Nirmala et al. (2009 [triangle]). For general background to the bridging of N—C bonds in pyrrolizine rings, see: Ramesh et al. (2007 [triangle]). For ring puckering parameters, see: Cremer & Pople (1975 [triangle]).

An external file that holds a picture, illustration, etc.
Object name is e-66-0o810-scheme1.jpg

Experimental

Crystal data

  • C26H24ClNO3
  • M r = 433.91
  • Monoclinic, An external file that holds a picture, illustration, etc.
Object name is e-66-0o810-efi1.jpg
  • a = 22.3214 (9) Å
  • b = 10.8122 (5) Å
  • c = 18.5008 (8) Å
  • β = 102.756 (3)°
  • V = 4354.8 (3) Å3
  • Z = 8
  • Mo Kα radiation
  • μ = 0.20 mm−1
  • T = 295 K
  • 0.20 × 0.20 × 0.20 mm

Data collection

  • Bruker Kappa APEXII diffractometer
  • Absorption correction: multi-scan (SADABS; Sheldrick, 1996 [triangle]) T min = 0.960, T max = 0.960
  • 40734 measured reflections
  • 10819 independent reflections
  • 5771 reflections with I > 2σ(I)
  • R int = 0.040

Refinement

  • R[F 2 > 2σ(F 2)] = 0.063
  • wR(F 2) = 0.201
  • S = 1.04
  • 10819 reflections
  • 571 parameters
  • 1 restraint
  • H-atom parameters constrained
  • Δρmax = 0.64 e Å−3
  • Δρmin = −0.55 e Å−3

Data collection: APEX2 (Bruker, 2004 [triangle]); cell refinement: SAINT (Bruker, 2004 [triangle]); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 [triangle]); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 [triangle]); molecular graphics: PLATON (Spek, 2009 [triangle]); software used to prepare material for publication: SHELXL97.

Table 1
Hydrogen-bond geometry (Å, °)

Supplementary Material

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536810007804/gk2258sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536810007804/gk2258Isup2.hkl

Additional supplementary materials: crystallographic information; 3D view; checkCIF report

Acknowledgments

BG thanks AMET University management, India, for their kind support.

supplementary crystallographic information

Comment

Chromenopyrrole compounds are used in the treatment of impulsive disorders (Caine, 1993), aggressiveness (Tidey, 1992), Parkinson's disease (Carlson, 1993), psychoses, memory disorders (Sokoloff et al., 1990), anxiety and depression (Wilner, 1985).

The geometric parameters of the title molecule (Fig. 1) agree well with reported similar structure (Nirmala et al., 2009). The pyrrolizine ring system is folded about the bridging N1—C17 bond for molecule (I) and N2—C43 bond for molecule (II), as observed in related structures (Ramesh et al., 2007; Nirmala et al., 2009). The dihedral angle between the naphthalene ring system and the chlorophenyl substituent is 58.76 (9) ° for molecule (I) and 51.59 (8) ° for molecule (II).

In the pyrrolizine ring system, both the pyrrolidine rings [N1/C14—C17, N1/C11/C12/C18/C17 for molecule (I) and N2/C40—C43, N2/C37/C38/C44/C43 for molecule (II)] adopt envelope conformations with the puckering parameters (Cremer and Pople, 1975) q2 = 0.3852 (2) Å and [var phi] 2 = 257.36 (2)° and q2 = 0.3627 (2) Å and [var phi] 2 = 71.35 (2)° respectively for molecule (I), q2 = 0.4343 (2) Å and [var phi] 2 = 242.94 (2) ° & q2 = 0.3354 (2) Å and [var phi] 2 = 89.25 (2) ° respectively for molecule (II).

The six-membered heterocyclic ring [C8/C9/C11/C12/C13/O1 for molecule (I) and C34/C35/C37/C38/C39/O4 for molecule (II)] of the benzochromenopyrrole moiety adopts a half-chair conformation with the puckering parameters (Cremer and Pople, 1975) Q = 0.4529 (2) Å, Θ = 132.97 (2) ° and [var phi] = 78.47 (2) ° for molecule (I) and Q = 0.4706 (2) Å, Θ = 132.03 (2) ° and [var phi] = 93.57 (2) ° for molecule (II) respectively. The sum of bond angles around N1 [334.10 (2) °] for molecule (I) and N2 [334.40 (2) °] for molecule (II) indicates the sp3 hybridization state of atoms N1 & N2.

The molecular structure is stabilized by weak intramolecular C—H···O interactions and the crystal packing is stabilized by weak C—H···π interactions[C14—H14A···Cg12(-X, -1/2+Y, 1/2-Z) distance of 3.951 (2) Å, C16—H16A···Cg11(-X, -1/2+Y, 1/2-Z) distance of 3.706 (2) Å, C21—H21···Cg11(-X, 1-Y, -Z) distance of 3.649 (2) Å and C26—H26B···Cg5 (1-X, 1/2+Y, 1/2-Z) distance of 3.555 (1) Å (Cg5, Cg11 & Cg12 are the centroid of the rings defined by the atoms C27/C28/C29/C30/C31/C36, C1/C2/C3/C4/C5/C10 & C5/C6/C7/C8/C9/C10 respectively)].

Experimental

A mixture of (Z)-methyl 2-((1-formylnaphthalen-2-yloxy) methyl) -3-(4-chloro phenylacrylate (20 mmol) and proline (30 mmol) were refluxed in benzene for 20 h and the solvent was removed under reduced pressure. The crude product was subjected to column chromatography to get the pure product. Chloroform and methanol (1:1) solvent mixture was used for the crystallization by slow evaporation method.

Refinement

The site occupancy factors of a disordered C atom were refined as C41 = 0.69 (2) and C41A = 0.31 (2) during anisotropic refinement. H atoms were positioned geometrically and refined using riding model with C—H = 0.93Å and Uiso(H) = 1.2Ueq(C) for aromatic, C—H = 0.98Å and Uiso(H) = 1.2Ueq(C) for methine, C—H = 0.97Å and Uiso(H) = 1.2Ueq(C) for methylene , C—H = 0.96Å and Uiso(H) = 1.5Ueq(C) for methyl groups. The components of the anisotropic displacement parameters in direction of the bond of C22 and C23, were restrained to be equal within an effective standard deviation of 0.001 using the DELU command in SHELXL97(Sheldrick, 2008).

Figures

Fig. 1.
The molecular structure of (I) and (II), with atom labels and 30% probability displacement ellipsoids for non-H atoms.

Crystal data

C26H24ClNO3F(000) = 1824
Mr = 433.91Dx = 1.324 Mg m3
Monoclinic, P21/cMo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybcCell parameters from 6164 reflections
a = 22.3214 (9) Åθ = 2.5–28.0°
b = 10.8122 (5) ŵ = 0.20 mm1
c = 18.5008 (8) ÅT = 295 K
β = 102.756 (3)°Block, colourless
V = 4354.8 (3) Å30.20 × 0.20 × 0.20 mm
Z = 8

Data collection

Bruker Kappa APEXII diffractometer10819 independent reflections
Radiation source: fine-focus sealed tube5771 reflections with I > 2σ(I)
graphiteRint = 0.040
Detector resolution: 0 pixels mm-1θmax = 28.3°, θmin = 0.9°
ω and [var phi] scansh = −29→29
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)k = −14→14
Tmin = 0.960, Tmax = 0.960l = −24→24
40734 measured reflections

Refinement

Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.063Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.201H-atom parameters constrained
S = 1.04w = 1/[σ2(Fo2) + (0.0823P)2 + 1.6776P] where P = (Fo2 + 2Fc2)/3
10819 reflections(Δ/σ)max = 0.031
571 parametersΔρmax = 0.64 e Å3
1 restraintΔρmin = −0.55 e Å3

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2)

xyzUiso*/UeqOcc. (<1)
C1−0.07636 (12)0.0026 (3)0.73870 (14)0.0533 (6)
H1−0.04700.06510.74700.064*
C2−0.12729 (14)0.0129 (3)0.76812 (16)0.0641 (8)
H2−0.13220.08230.79600.077*
C3−0.17171 (14)−0.0793 (3)0.75678 (17)0.0694 (9)
H3−0.2068−0.07010.77560.083*
C4−0.16401 (13)−0.1825 (3)0.71836 (16)0.0631 (8)
H4−0.1936−0.24450.71190.076*
C5−0.11179 (12)−0.1972 (3)0.68793 (14)0.0506 (6)
C6−0.10198 (13)−0.3072 (3)0.65035 (15)0.0581 (7)
H6−0.1306−0.37090.64520.070*
C7−0.05150 (12)−0.3204 (2)0.62199 (15)0.0539 (6)
H7−0.0449−0.39400.59900.065*
C8−0.00902 (11)−0.2231 (2)0.62717 (13)0.0455 (6)
C9−0.01553 (11)−0.1132 (2)0.66223 (12)0.0431 (5)
C10−0.06751 (11)−0.1020 (2)0.69571 (12)0.0450 (6)
C110.03076 (10)−0.0100 (2)0.66425 (13)0.0425 (5)
H110.04130.02520.71430.051*
C120.08965 (11)−0.0557 (2)0.64277 (13)0.0447 (6)
C130.07239 (11)−0.1440 (2)0.57766 (13)0.0474 (6)
H13A0.0472−0.10080.53590.057*
H13B0.1094−0.17170.56320.057*
C14−0.02061 (14)0.1973 (2)0.63721 (16)0.0601 (7)
H14A−0.00450.20970.68990.072*
H14B−0.06480.18670.62830.072*
C15−0.00443 (14)0.3051 (3)0.59322 (16)0.0606 (7)
H15A−0.03230.31030.54500.073*
H15B−0.00560.38250.61940.073*
C160.05997 (14)0.2756 (3)0.58591 (17)0.0636 (8)
H16A0.09000.30210.62950.076*
H16B0.06910.31500.54250.076*
C170.05954 (11)0.1360 (2)0.57842 (15)0.0516 (6)
H170.05110.11470.52570.062*
C180.11705 (11)0.0657 (3)0.61847 (14)0.0507 (6)
H180.13490.11200.66360.061*
C190.16677 (12)0.0508 (3)0.57547 (15)0.0538 (6)
C200.15403 (14)0.0320 (3)0.49928 (16)0.0648 (8)
H200.11330.02940.47320.078*
C210.20021 (16)0.0171 (3)0.46145 (19)0.0745 (9)
H210.19060.00330.41060.089*
C220.25994 (16)0.0226 (3)0.4986 (2)0.0781 (9)
C230.27455 (15)0.0397 (4)0.5730 (2)0.0866 (10)
H230.31550.04170.59820.104*
C240.22811 (13)0.0542 (3)0.61148 (19)0.0744 (9)
H240.23850.06650.66250.089*
C250.13534 (11)−0.1199 (3)0.70353 (14)0.0497 (6)
C260.17634 (18)−0.1413 (4)0.83147 (17)0.0989 (13)
H26A0.1757−0.22980.82670.148*
H26B0.1669−0.11890.87790.148*
H26C0.2164−0.11080.82970.148*
C270.27507 (12)−0.1797 (3)1.01938 (14)0.0554 (7)
H270.2977−0.25161.01830.067*
C280.22600 (14)−0.1821 (3)1.05207 (16)0.0714 (9)
H280.2159−0.25511.07310.086*
C290.19090 (15)−0.0768 (4)1.05429 (18)0.0810 (10)
H290.1575−0.07931.07670.097*
C300.20549 (14)0.0296 (4)1.02362 (17)0.0747 (9)
H300.18220.10021.02590.090*
C310.25532 (12)0.0358 (3)0.98824 (14)0.0561 (7)
C320.26886 (14)0.1441 (3)0.95261 (17)0.0656 (8)
H320.24540.21480.95380.079*
C330.31533 (14)0.1470 (3)0.91679 (17)0.0636 (7)
H330.32300.21870.89250.076*
C340.35220 (12)0.0419 (3)0.91605 (14)0.0513 (6)
C350.34343 (11)−0.0648 (2)0.95212 (13)0.0454 (6)
C360.29225 (11)−0.0707 (2)0.98716 (13)0.0464 (6)
C370.38691 (12)−0.1712 (2)0.95372 (14)0.0503 (6)
H370.3648−0.24980.95170.060*
C380.42144 (11)−0.1641 (3)0.89047 (14)0.0515 (6)
C390.44475 (12)−0.0338 (3)0.88659 (15)0.0552 (7)
H39A0.4746−0.01550.93200.066*
H39B0.4655−0.02790.84580.066*
C400.42860 (16)−0.2218 (4)1.08863 (17)0.0810 (10)
H40A0.3924−0.27411.07870.097*
H40B0.4230−0.15751.12310.097*
C420.5073 (2)−0.3374 (4)1.05483 (19)0.0912 (12)
H42A0.4861−0.41141.03310.109*
H42B0.5512−0.35331.06760.109*
C430.49248 (15)−0.2293 (3)1.00385 (17)0.0700 (8)
H430.5272−0.17161.01430.084*
C440.47562 (13)−0.2556 (3)0.91870 (16)0.0611 (7)
H440.4591−0.33980.91170.073*
C450.52890 (12)−0.2479 (3)0.88104 (14)0.0521 (6)
C460.57228 (13)−0.1541 (3)0.89731 (17)0.0672 (8)
H460.5694−0.09660.93380.081*
C470.61934 (13)−0.1444 (3)0.86064 (18)0.0711 (9)
H470.6477−0.08040.87170.085*
C480.62386 (13)−0.2299 (3)0.80779 (17)0.0690 (8)
C490.58322 (14)−0.3254 (3)0.79190 (17)0.0719 (9)
H490.5877−0.38510.75720.086*
C500.53543 (13)−0.3326 (3)0.82786 (16)0.0633 (8)
H500.5069−0.39620.81590.076*
C510.38363 (13)−0.2008 (3)0.81484 (17)0.0628 (7)
C520.3130 (2)−0.3414 (5)0.7477 (2)0.1147 (15)
H52A0.2933−0.27280.71910.172*
H52B0.2824−0.39820.75680.172*
H52C0.3394−0.38270.72100.172*
N10.00836 (9)0.08961 (18)0.61034 (11)0.0453 (5)
N20.43864 (10)−0.1676 (2)1.02015 (12)0.0621 (6)
O10.03955 (8)−0.24894 (16)0.59566 (10)0.0536 (4)
O20.17254 (10)−0.1925 (2)0.69264 (11)0.0794 (7)
O30.13110 (10)−0.0879 (2)0.77133 (10)0.0796 (7)
O40.39666 (9)0.05623 (18)0.87646 (11)0.0625 (5)
O50.38716 (15)−0.1522 (3)0.75852 (13)0.1160 (10)
O60.34906 (11)−0.2967 (2)0.81782 (12)0.0883 (7)
Cl10.31782 (5)0.00823 (10)0.44984 (8)0.1211 (5)
Cl20.68286 (5)−0.21687 (13)0.76101 (7)0.1163 (4)
C410.4847 (5)−0.2963 (9)1.1198 (4)0.077 (2)0.69 (2)
H41A0.5153−0.24621.15230.092*0.69 (2)
H41B0.4746−0.36661.14740.092*0.69 (2)
C41A0.4516 (12)−0.3365 (15)1.0949 (12)0.080 (5)0.31 (2)
H41C0.4206−0.39541.07170.096*0.31 (2)
H41D0.4656−0.35851.14670.096*0.31 (2)

Atomic displacement parameters (Å2)

U11U22U33U12U13U23
C10.0563 (15)0.0537 (16)0.0517 (14)0.0058 (13)0.0160 (12)0.0046 (13)
C20.0726 (19)0.0651 (19)0.0601 (17)0.0156 (16)0.0267 (15)0.0091 (14)
C30.0559 (17)0.087 (2)0.0709 (19)0.0122 (17)0.0256 (15)0.0190 (18)
C40.0485 (15)0.074 (2)0.0658 (17)−0.0056 (14)0.0099 (13)0.0191 (16)
C50.0484 (14)0.0522 (16)0.0482 (13)−0.0007 (12)0.0039 (11)0.0109 (12)
C60.0570 (16)0.0504 (16)0.0621 (16)−0.0125 (13)0.0027 (13)0.0094 (14)
C70.0607 (16)0.0391 (14)0.0580 (15)−0.0042 (12)0.0046 (13)−0.0008 (12)
C80.0466 (13)0.0433 (14)0.0441 (13)0.0030 (11)0.0050 (10)0.0010 (11)
C90.0431 (13)0.0435 (14)0.0396 (12)0.0019 (11)0.0022 (10)0.0007 (10)
C100.0467 (13)0.0461 (14)0.0397 (12)0.0045 (11)0.0041 (10)0.0065 (11)
C110.0430 (12)0.0414 (13)0.0401 (12)0.0009 (11)0.0028 (10)−0.0042 (10)
C120.0404 (12)0.0469 (14)0.0452 (13)0.0007 (11)0.0056 (10)−0.0050 (11)
C130.0450 (13)0.0482 (14)0.0489 (13)0.0010 (11)0.0102 (11)−0.0073 (12)
C140.0701 (18)0.0437 (15)0.0685 (17)0.0104 (14)0.0196 (14)−0.0036 (13)
C150.078 (2)0.0399 (14)0.0595 (16)0.0069 (14)0.0053 (14)−0.0064 (13)
C160.0706 (19)0.0463 (16)0.0682 (18)−0.0064 (14)0.0032 (15)0.0058 (14)
C170.0484 (14)0.0508 (15)0.0532 (14)−0.0007 (12)0.0062 (12)−0.0016 (12)
C180.0444 (13)0.0535 (16)0.0518 (14)−0.0036 (12)0.0053 (11)−0.0051 (12)
C190.0455 (14)0.0514 (16)0.0641 (17)−0.0019 (12)0.0113 (12)0.0039 (13)
C200.0602 (17)0.073 (2)0.0630 (18)0.0105 (15)0.0176 (14)0.0129 (15)
C210.084 (2)0.072 (2)0.076 (2)0.0168 (18)0.0353 (18)0.0229 (17)
C220.072 (2)0.0567 (19)0.119 (2)0.0069 (16)0.050 (2)0.0200 (19)
C230.0443 (17)0.088 (3)0.127 (2)−0.0065 (17)0.0175 (19)−0.003 (2)
C240.0461 (16)0.088 (2)0.085 (2)−0.0089 (16)0.0061 (15)−0.0102 (19)
C250.0447 (14)0.0540 (16)0.0474 (14)0.0028 (12)0.0036 (11)−0.0038 (12)
C260.108 (3)0.115 (3)0.0555 (18)0.041 (3)−0.0202 (19)−0.007 (2)
C270.0509 (15)0.0674 (18)0.0502 (14)−0.0046 (13)0.0160 (12)−0.0017 (13)
C280.0662 (19)0.091 (2)0.0635 (18)−0.0082 (18)0.0277 (15)0.0031 (17)
C290.070 (2)0.116 (3)0.068 (2)0.002 (2)0.0381 (17)−0.001 (2)
C300.0666 (19)0.094 (3)0.0678 (19)0.0193 (18)0.0241 (16)−0.0140 (19)
C310.0545 (16)0.0656 (19)0.0474 (14)0.0027 (14)0.0093 (12)−0.0116 (13)
C320.0655 (18)0.0573 (18)0.0724 (19)0.0120 (15)0.0122 (15)−0.0107 (15)
C330.0723 (19)0.0487 (16)0.0681 (18)0.0009 (15)0.0118 (15)0.0030 (14)
C340.0491 (14)0.0536 (16)0.0511 (14)−0.0029 (12)0.0107 (12)0.0007 (12)
C350.0436 (13)0.0488 (14)0.0435 (13)−0.0030 (11)0.0091 (10)−0.0038 (11)
C360.0441 (13)0.0550 (16)0.0396 (12)−0.0003 (12)0.0079 (10)−0.0060 (11)
C370.0530 (15)0.0497 (15)0.0529 (14)−0.0006 (12)0.0218 (12)0.0035 (12)
C380.0482 (14)0.0588 (17)0.0509 (14)−0.0023 (13)0.0182 (12)0.0007 (12)
C390.0483 (14)0.0633 (18)0.0562 (15)0.0002 (13)0.0165 (12)0.0087 (13)
C400.080 (2)0.112 (3)0.0537 (17)0.014 (2)0.0214 (16)0.0244 (19)
C420.119 (3)0.076 (2)0.070 (2)0.036 (2)0.005 (2)0.0069 (18)
C430.073 (2)0.078 (2)0.0632 (17)0.0127 (17)0.0224 (15)0.0039 (16)
C440.0578 (16)0.0643 (18)0.0666 (17)0.0092 (14)0.0251 (14)0.0030 (15)
C450.0490 (14)0.0588 (16)0.0496 (14)0.0066 (13)0.0134 (11)−0.0037 (13)
C460.0606 (17)0.075 (2)0.0661 (18)−0.0013 (16)0.0133 (14)−0.0255 (16)
C470.0482 (16)0.078 (2)0.086 (2)−0.0123 (15)0.0132 (15)−0.0168 (18)
C480.0539 (17)0.089 (2)0.0698 (19)−0.0023 (17)0.0254 (14)−0.0062 (18)
C490.074 (2)0.083 (2)0.0637 (18)−0.0030 (18)0.0258 (16)−0.0267 (17)
C500.0580 (16)0.0649 (19)0.0680 (18)−0.0074 (14)0.0159 (14)−0.0148 (15)
C510.0601 (17)0.073 (2)0.0603 (17)−0.0082 (15)0.0238 (14)−0.0043 (16)
C520.109 (3)0.126 (4)0.105 (3)−0.038 (3)0.014 (3)−0.046 (3)
N10.0470 (11)0.0398 (11)0.0488 (11)0.0032 (9)0.0102 (9)−0.0035 (9)
N20.0550 (13)0.0814 (18)0.0520 (12)0.0137 (12)0.0163 (11)0.0146 (12)
O10.0583 (11)0.0422 (10)0.0610 (11)0.0004 (8)0.0149 (9)−0.0101 (8)
O20.0765 (14)0.0942 (17)0.0653 (12)0.0387 (13)0.0108 (11)0.0031 (12)
O30.0849 (15)0.0937 (17)0.0486 (11)0.0366 (13)−0.0099 (10)−0.0138 (11)
O40.0589 (11)0.0575 (12)0.0757 (13)0.0010 (9)0.0248 (10)0.0177 (10)
O50.150 (3)0.135 (3)0.0572 (14)−0.053 (2)0.0100 (15)0.0066 (15)
O60.1044 (18)0.0896 (17)0.0706 (14)−0.0384 (15)0.0188 (13)−0.0166 (13)
Cl10.1133 (8)0.0878 (7)0.1952 (13)0.0268 (6)0.1052 (9)0.0392 (7)
Cl20.0892 (7)0.1540 (11)0.1256 (9)−0.0129 (7)0.0664 (6)−0.0095 (8)
C410.096 (6)0.072 (4)0.057 (3)0.006 (4)0.007 (3)0.005 (3)
C41A0.109 (13)0.061 (8)0.066 (9)−0.010 (8)0.009 (9)0.023 (6)

Geometric parameters (Å, °)

C1—C21.369 (4)C27—H270.9300
C1—C101.421 (4)C28—C291.388 (5)
C1—H10.9300C28—H280.9300
C2—C31.389 (4)C29—C301.354 (5)
C2—H20.9300C29—H290.9300
C3—C41.354 (4)C30—C311.411 (4)
C3—H30.9300C30—H300.9300
C4—C51.411 (4)C31—C321.409 (4)
C4—H40.9300C31—C361.419 (4)
C5—C101.412 (4)C32—C331.349 (4)
C5—C61.418 (4)C32—H320.9300
C6—C71.351 (4)C33—C341.405 (4)
C6—H60.9300C33—H330.9300
C7—C81.405 (4)C34—O41.366 (3)
C7—H70.9300C34—C351.369 (4)
C8—O11.368 (3)C35—C361.434 (3)
C8—C91.376 (3)C35—C371.501 (4)
C9—C101.436 (3)C37—N21.489 (4)
C9—C111.516 (3)C37—C381.539 (3)
C11—N11.478 (3)C37—H370.9800
C11—C121.536 (3)C38—C391.509 (4)
C11—H110.9800C38—C511.518 (4)
C12—C251.510 (3)C38—C441.561 (4)
C12—C131.519 (3)C39—O41.430 (3)
C12—C181.555 (4)C39—H39A0.9700
C13—O11.429 (3)C39—H39B0.9700
C13—H13A0.9700C40—C41A1.338 (14)
C13—H13B0.9700C40—N21.457 (4)
C14—N11.471 (3)C40—C411.493 (8)
C14—C151.510 (4)C40—H40A0.9700
C14—H14A0.9700C40—H40B0.9700
C14—H14B0.9700C42—C411.471 (7)
C15—C161.507 (4)C42—C431.492 (5)
C15—H15A0.9700C42—C41A1.582 (17)
C15—H15B0.9700C42—H42A0.9700
C16—C171.516 (4)C42—H42B0.9700
C16—H16A0.9700C43—N21.463 (4)
C16—H16B0.9700C43—C441.563 (4)
C17—N11.484 (3)C43—H430.9800
C17—C181.535 (4)C44—C451.507 (4)
C17—H170.9800C44—H440.9800
C18—C191.510 (3)C45—C501.375 (4)
C18—H180.9800C45—C461.388 (4)
C19—C241.385 (4)C46—C471.375 (4)
C19—C201.390 (4)C46—H460.9300
C20—C211.377 (4)C47—C481.365 (4)
C20—H200.9300C47—H470.9300
C21—C221.360 (5)C48—C491.364 (4)
C21—H210.9300C48—Cl21.734 (3)
C22—C231.355 (5)C49—C501.378 (4)
C22—Cl11.739 (3)C49—H490.9300
C23—C241.390 (4)C50—H500.9300
C23—H230.9300C51—O51.185 (3)
C24—H240.9300C51—O61.301 (4)
C25—O21.192 (3)C52—O61.450 (4)
C25—O31.325 (3)C52—H52A0.9600
C26—O31.448 (4)C52—H52B0.9600
C26—H26A0.9600C52—H52C0.9600
C26—H26B0.9600C41—H41A0.9700
C26—H26C0.9600C41—H41B0.9700
C27—C281.363 (4)C41A—H41C0.9700
C27—C361.411 (4)C41A—H41D0.9700
C2—C1—C10121.2 (3)C32—C31—C30121.9 (3)
C2—C1—H1119.4C32—C31—C36118.9 (2)
C10—C1—H1119.4C30—C31—C36119.2 (3)
C1—C2—C3120.6 (3)C33—C32—C31121.1 (3)
C1—C2—H2119.7C33—C32—H32119.4
C3—C2—H2119.7C31—C32—H32119.4
C4—C3—C2120.1 (3)C32—C33—C34120.1 (3)
C4—C3—H3119.9C32—C33—H33120.0
C2—C3—H3119.9C34—C33—H33120.0
C3—C4—C5121.0 (3)O4—C34—C35123.8 (2)
C3—C4—H4119.5O4—C34—C33114.2 (2)
C5—C4—H4119.5C35—C34—C33122.0 (2)
C4—C5—C10119.9 (3)C34—C35—C36118.2 (2)
C4—C5—C6121.4 (3)C34—C35—C37119.6 (2)
C10—C5—C6118.7 (2)C36—C35—C37122.2 (2)
C7—C6—C5120.8 (3)C27—C36—C31117.3 (2)
C7—C6—H6119.6C27—C36—C35123.1 (2)
C5—C6—H6119.6C31—C36—C35119.6 (2)
C6—C7—C8120.1 (3)N2—C37—C35112.1 (2)
C6—C7—H7119.9N2—C37—C38101.48 (19)
C8—C7—H7119.9C35—C37—C38112.2 (2)
O1—C8—C9123.6 (2)N2—C37—H37110.3
O1—C8—C7113.8 (2)C35—C37—H37110.3
C9—C8—C7122.6 (2)C38—C37—H37110.3
C8—C9—C10117.1 (2)C39—C38—C51109.1 (2)
C8—C9—C11120.3 (2)C39—C38—C37108.6 (2)
C10—C9—C11122.6 (2)C51—C38—C37114.7 (2)
C5—C10—C1117.2 (2)C39—C38—C44111.0 (2)
C5—C10—C9120.6 (2)C51—C38—C44112.0 (2)
C1—C10—C9122.3 (2)C37—C38—C44101.3 (2)
N1—C11—C9113.13 (18)O4—C39—C38112.6 (2)
N1—C11—C12103.94 (18)O4—C39—H39A109.1
C9—C11—C12112.0 (2)C38—C39—H39A109.1
N1—C11—H11109.2O4—C39—H39B109.1
C9—C11—H11109.2C38—C39—H39B109.1
C12—C11—H11109.2H39A—C39—H39B107.8
C25—C12—C13108.2 (2)C41A—C40—N2108.5 (6)
C25—C12—C11115.5 (2)C41A—C40—C4136.2 (9)
C13—C12—C11109.01 (19)N2—C40—C41106.0 (3)
C25—C12—C18111.1 (2)C41A—C40—H40A76.4
C13—C12—C18110.4 (2)N2—C40—H40A110.5
C11—C12—C18102.53 (19)C41—C40—H40A110.5
O1—C13—C12111.57 (19)C41A—C40—H40B135.2
O1—C13—H13A109.3N2—C40—H40B110.5
C12—C13—H13A109.3C41—C40—H40B110.5
O1—C13—H13B109.3H40A—C40—H40B108.7
C12—C13—H13B109.3C41—C42—C43102.2 (3)
H13A—C13—H13B108.0C41—C42—C41A33.7 (6)
N1—C14—C15104.7 (2)C43—C42—C41A101.7 (5)
N1—C14—H14A110.8C41—C42—H42A111.3
C15—C14—H14A110.8C43—C42—H42A111.3
N1—C14—H14B110.8C41A—C42—H42A80.7
C15—C14—H14B110.8C41—C42—H42B111.3
H14A—C14—H14B108.9C43—C42—H42B111.3
C16—C15—C14103.4 (2)C41A—C42—H42B137.9
C16—C15—H15A111.1H42A—C42—H42B109.2
C14—C15—H15A111.1N2—C43—C42107.7 (3)
C16—C15—H15B111.1N2—C43—C44105.3 (2)
C14—C15—H15B111.1C42—C43—C44117.7 (3)
H15A—C15—H15B109.1N2—C43—H43108.6
C15—C16—C17103.4 (2)C42—C43—H43108.6
C15—C16—H16A111.1C44—C43—H43108.6
C17—C16—H16A111.1C45—C44—C38116.3 (2)
C15—C16—H16B111.1C45—C44—C43114.6 (2)
C17—C16—H16B111.1C38—C44—C43102.6 (2)
H16A—C16—H16B109.0C45—C44—H44107.6
N1—C17—C16106.9 (2)C38—C44—H44107.6
N1—C17—C18106.0 (2)C43—C44—H44107.6
C16—C17—C18117.5 (2)C50—C45—C46117.5 (2)
N1—C17—H17108.7C50—C45—C44120.9 (3)
C16—C17—H17108.7C46—C45—C44121.6 (2)
C18—C17—H17108.7C47—C46—C45121.4 (3)
C19—C18—C17115.6 (2)C47—C46—H46119.3
C19—C18—C12116.4 (2)C45—C46—H46119.3
C17—C18—C12102.54 (19)C48—C47—C46119.2 (3)
C19—C18—H18107.3C48—C47—H47120.4
C17—C18—H18107.3C46—C47—H47120.4
C12—C18—H18107.3C49—C48—C47121.1 (3)
C24—C19—C20116.8 (3)C49—C48—Cl2119.8 (2)
C24—C19—C18120.5 (3)C47—C48—Cl2119.2 (3)
C20—C19—C18122.7 (2)C48—C49—C50119.2 (3)
C21—C20—C19121.6 (3)C48—C49—H49120.4
C21—C20—H20119.2C50—C49—H49120.4
C19—C20—H20119.2C45—C50—C49121.6 (3)
C22—C21—C20119.9 (3)C45—C50—H50119.2
C22—C21—H21120.1C49—C50—H50119.2
C20—C21—H21120.1O5—C51—O6123.1 (3)
C23—C22—C21120.6 (3)O5—C51—C38124.3 (3)
C23—C22—Cl1120.0 (3)O6—C51—C38112.5 (3)
C21—C22—Cl1119.4 (3)O6—C52—H52A109.5
C22—C23—C24119.7 (3)O6—C52—H52B109.5
C22—C23—H23120.1H52A—C52—H52B109.5
C24—C23—H23120.1O6—C52—H52C109.5
C19—C24—C23121.4 (3)H52A—C52—H52C109.5
C19—C24—H24119.3H52B—C52—H52C109.5
C23—C24—H24119.3C14—N1—C11117.21 (19)
O2—C25—O3122.1 (2)C14—N1—C17107.5 (2)
O2—C25—C12124.0 (2)C11—N1—C17109.84 (18)
O3—C25—C12114.0 (2)C40—N2—C43106.7 (2)
O3—C26—H26A109.5C40—N2—C37117.8 (2)
O3—C26—H26B109.5C43—N2—C37109.9 (2)
H26A—C26—H26B109.5C8—O1—C13115.63 (19)
O3—C26—H26C109.5C25—O3—C26116.1 (2)
H26A—C26—H26C109.5C34—O4—C39117.8 (2)
H26B—C26—H26C109.5C51—O6—C52116.4 (3)
C28—C27—C36121.5 (3)C42—C41—C40105.0 (5)
C28—C27—H27119.2C42—C41—H41A110.8
C36—C27—H27119.2C40—C41—H41A110.8
C27—C28—C29120.8 (3)C42—C41—H41B110.8
C27—C28—H28119.6C40—C41—H41B110.8
C29—C28—H28119.6H41A—C41—H41B108.8
C30—C29—C28119.7 (3)C40—C41A—C42107.0 (10)
C30—C29—H29120.2C40—C41A—H41C110.3
C28—C29—H29120.2C42—C41A—H41C110.3
C29—C30—C31121.4 (3)C40—C41A—H41D110.3
C29—C30—H30119.3C42—C41A—H41D110.3
C31—C30—H30119.3H41C—C41A—H41D108.6
C10—C1—C2—C30.2 (4)C34—C35—C36—C27173.4 (2)
C1—C2—C3—C42.1 (5)C37—C35—C36—C27−6.4 (4)
C2—C3—C4—C5−1.4 (4)C34—C35—C36—C31−4.6 (3)
C3—C4—C5—C10−1.7 (4)C37—C35—C36—C31175.6 (2)
C3—C4—C5—C6177.3 (3)C34—C35—C37—N291.9 (3)
C4—C5—C6—C7−179.5 (2)C36—C35—C37—N2−88.3 (3)
C10—C5—C6—C7−0.5 (4)C34—C35—C37—C38−21.6 (3)
C5—C6—C7—C8−2.3 (4)C36—C35—C37—C38158.2 (2)
C6—C7—C8—O1−179.5 (2)N2—C37—C38—C39−73.7 (3)
C6—C7—C8—C91.7 (4)C35—C37—C38—C3946.2 (3)
O1—C8—C9—C10−177.1 (2)N2—C37—C38—C51164.0 (2)
C7—C8—C9—C101.5 (3)C35—C37—C38—C51−76.2 (3)
O1—C8—C9—C113.2 (4)N2—C37—C38—C4443.2 (3)
C7—C8—C9—C11−178.2 (2)C35—C37—C38—C44163.0 (2)
C4—C5—C10—C13.9 (3)C51—C38—C39—O468.7 (3)
C6—C5—C10—C1−175.1 (2)C37—C38—C39—O4−57.0 (3)
C4—C5—C10—C9−177.2 (2)C44—C38—C39—O4−167.5 (2)
C6—C5—C10—C93.8 (3)C41—C42—C43—N2−28.8 (7)
C2—C1—C10—C5−3.2 (4)C41A—C42—C43—N25.7 (11)
C2—C1—C10—C9177.9 (2)C41—C42—C43—C44−147.6 (6)
C8—C9—C10—C5−4.3 (3)C41A—C42—C43—C44−113.1 (11)
C11—C9—C10—C5175.5 (2)C39—C38—C44—C45−49.2 (3)
C8—C9—C10—C1174.6 (2)C51—C38—C44—C4573.0 (3)
C11—C9—C10—C1−5.6 (3)C37—C38—C44—C45−164.3 (2)
C8—C9—C11—N1102.2 (2)C39—C38—C44—C4376.8 (3)
C10—C9—C11—N1−77.5 (3)C51—C38—C44—C43−161.0 (2)
C8—C9—C11—C12−14.9 (3)C37—C38—C44—C43−38.3 (3)
C10—C9—C11—C12165.4 (2)N2—C43—C44—C45146.1 (3)
N1—C11—C12—C25157.0 (2)C42—C43—C44—C45−93.8 (4)
C9—C11—C12—C25−80.6 (3)N2—C43—C44—C3819.1 (3)
N1—C11—C12—C13−80.9 (2)C42—C43—C44—C38139.2 (3)
C9—C11—C12—C1341.5 (3)C38—C44—C45—C50−101.4 (3)
N1—C11—C12—C1836.0 (2)C43—C44—C45—C50139.0 (3)
C9—C11—C12—C18158.50 (19)C38—C44—C45—C4677.1 (4)
C25—C12—C13—O166.2 (2)C43—C44—C45—C46−42.5 (4)
C11—C12—C13—O1−60.2 (3)C50—C45—C46—C471.3 (5)
C18—C12—C13—O1−172.10 (19)C44—C45—C46—C47−177.2 (3)
N1—C14—C15—C16−36.6 (3)C45—C46—C47—C48−0.9 (5)
C14—C15—C16—C1735.5 (3)C46—C47—C48—C49−1.2 (5)
C15—C16—C17—N1−21.8 (3)C46—C47—C48—Cl2179.5 (3)
C15—C16—C17—C18−140.6 (2)C47—C48—C49—C502.6 (5)
N1—C17—C18—C19153.3 (2)Cl2—C48—C49—C50−178.0 (3)
C16—C17—C18—C19−87.4 (3)C46—C45—C50—C490.2 (4)
N1—C17—C18—C1225.6 (2)C44—C45—C50—C49178.7 (3)
C16—C17—C18—C12144.9 (2)C48—C49—C50—C45−2.1 (5)
C25—C12—C18—C1971.1 (3)C39—C38—C51—O520.7 (4)
C13—C12—C18—C19−48.9 (3)C37—C38—C51—O5142.7 (3)
C11—C12—C18—C19−164.9 (2)C44—C38—C51—O5−102.6 (4)
C25—C12—C18—C17−161.7 (2)C39—C38—C51—O6−163.0 (2)
C13—C12—C18—C1778.3 (2)C37—C38—C51—O6−41.0 (4)
C11—C12—C18—C17−37.7 (2)C44—C38—C51—O673.7 (3)
C17—C18—C19—C24144.5 (3)C15—C14—N1—C11147.4 (2)
C12—C18—C19—C24−95.1 (3)C15—C14—N1—C1723.1 (3)
C17—C18—C19—C20−36.2 (4)C9—C11—N1—C1494.5 (3)
C12—C18—C19—C2084.2 (3)C12—C11—N1—C14−143.8 (2)
C24—C19—C20—C210.2 (5)C9—C11—N1—C17−142.5 (2)
C18—C19—C20—C21−179.2 (3)C12—C11—N1—C17−20.8 (2)
C19—C20—C21—C22−1.0 (5)C16—C17—N1—C14−0.8 (3)
C20—C21—C22—C231.6 (5)C18—C17—N1—C14125.3 (2)
C20—C21—C22—Cl1−178.1 (2)C16—C17—N1—C11−129.4 (2)
C21—C22—C23—C24−1.3 (6)C18—C17—N1—C11−3.3 (3)
Cl1—C22—C23—C24178.4 (3)C41A—C40—N2—C43−26.4 (14)
C20—C19—C24—C230.1 (5)C41—C40—N2—C4311.5 (6)
C18—C19—C24—C23179.5 (3)C41A—C40—N2—C3797.7 (14)
C22—C23—C24—C190.4 (5)C41—C40—N2—C37135.6 (6)
C13—C12—C25—O233.3 (4)C42—C43—N2—C4010.8 (4)
C11—C12—C25—O2155.8 (3)C44—C43—N2—C40137.3 (3)
C18—C12—C25—O2−88.0 (3)C42—C43—N2—C37−118.0 (3)
C13—C12—C25—O3−147.2 (2)C44—C43—N2—C378.4 (3)
C11—C12—C25—O3−24.8 (3)C35—C37—N2—C4084.8 (3)
C18—C12—C25—O391.5 (3)C38—C37—N2—C40−155.3 (3)
C36—C27—C28—C290.4 (4)C35—C37—N2—C43−152.7 (2)
C27—C28—C29—C300.0 (5)C38—C37—N2—C43−32.8 (3)
C28—C29—C30—C310.9 (5)C9—C8—O1—C13−21.0 (3)
C29—C30—C31—C32176.5 (3)C7—C8—O1—C13160.3 (2)
C29—C30—C31—C36−2.3 (4)C12—C13—O1—C850.0 (3)
C30—C31—C32—C33−177.6 (3)O2—C25—O3—C263.1 (5)
C36—C31—C32—C331.2 (4)C12—C25—O3—C26−176.4 (3)
C31—C32—C33—C34−1.6 (4)C35—C34—O4—C39−14.4 (4)
C32—C33—C34—O4178.6 (3)C33—C34—O4—C39165.8 (2)
C32—C33—C34—C35−1.3 (4)C38—C39—O4—C3441.8 (3)
O4—C34—C35—C36−175.5 (2)O5—C51—O6—C52−1.4 (5)
C33—C34—C35—C364.3 (4)C38—C51—O6—C52−177.7 (3)
O4—C34—C35—C374.3 (4)C43—C42—C41—C4035.3 (8)
C33—C34—C35—C37−175.9 (2)C41A—C42—C41—C40−57.7 (9)
C28—C27—C36—C31−1.7 (4)C41A—C40—C41—C4269.9 (11)
C28—C27—C36—C35−179.8 (2)N2—C40—C41—C42−29.8 (9)
C32—C31—C36—C27−176.2 (2)N2—C40—C41A—C4230.0 (19)
C30—C31—C36—C272.6 (4)C41—C40—C41A—C42−61.9 (14)
C32—C31—C36—C352.0 (4)C41—C42—C41A—C4072.3 (15)
C30—C31—C36—C35−179.2 (2)C43—C42—C41A—C40−22.1 (18)

Hydrogen-bond geometry (Å, °)

Cg5, Cg11 and Cg12 are the centroids of the C27–C31/C36, C1–C5/C10 and C5–C10 rings, respectively.
D—H···AD—HH···AD···AD—H···A
C11—H11···O30.982.392.773 (3)103
C37—H37···O60.982.482.818 (3)100
C14—H14A···Cg12i0.973.003.951 (2)168
C16—H16A···Cg11i0.972.833.706 (2)151
C21—H21···Cg11ii0.932.853.649 (2)144
C26—H26B···Cg5iii0.962.833.555 (1)133

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

Footnotes

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: GK2258).

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