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In the title compound, C30H24N2O, the pyrrolidine ring adopts a twist conformation. The dihedral angle between the fluorene ring system and the phenyl ring is 68.3 (1)°. In the solid state, inversion-related mol­ecules form dimers via N—H...O hydrogen bonds. Weak C—H...π interactions also stabilize the molecular packing.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536804026911/wn6298sup1.cif
Contains datablocks I, global

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536804026911/wn6298Isup2.hkl
Contains datablock I

CCDC reference: 255947

Key indicators

  • Single-crystal X-ray study
  • T = 273 K
  • Mean [sigma](C-C) = 0.006 Å
  • R factor = 0.080
  • wR factor = 0.179
  • Data-to-parameter ratio = 13.5

checkCIF/PLATON results

No syntax errors found



Alert level A DIFF020_ALERT_1_A _diffrn_standards_interval_count and _diffrn_standards_interval_time are missing. Number of measurements between standards or time (min) between standards. DIFF022_ALERT_1_A _diffrn_standards_decay_% is missing Percentage decrease in standards intensity. PLAT029_ALERT_3_A _diffrn_measured_fraction_theta_full Low ....... 0.90 PLAT480_ALERT_4_A Long H...A H-Bond Reported H6 .. CGB .. 3.00 Ang.
Alert level B PLAT480_ALERT_4_B Long H...A H-Bond Reported H19 .. CGA .. 2.89 Ang.
Alert level C PLAT141_ALERT_4_C su on a - Axis Small or Missing (x 100000) ..... 10 Ang. PLAT143_ALERT_4_C su on c - Axis Small or Missing (x 100000) ..... 10 Ang. PLAT152_ALERT_1_C Supplied and Calc Volume s.u. Inconsistent ..... ? PLAT220_ALERT_2_C Large Non-Solvent C Ueq(max)/Ueq(min) ... 3.05 Ratio PLAT242_ALERT_2_C Check Low U(eq) as Compared to Neighbors for C24 PLAT340_ALERT_3_C Low Bond Precision on C-C bonds (x 1000) Ang ... 6 PLAT481_ALERT_4_C Long D...A H-Bond Reported C19 .. CGA .. 3.79 Ang.
4 ALERT level A = In general: serious problem 1 ALERT level B = Potentially serious problem 7 ALERT level C = Check and explain 0 ALERT level G = General alerts; check 3 ALERT type 1 CIF construction/syntax error, inconsistent or missing data 2 ALERT type 2 Indicator that the structure model may be wrong or deficient 2 ALERT type 3 Indicator that the structure quality may be low 5 ALERT type 4 Improvement, methodology, query or suggestion

Computing details top

Data collection: SMART (Bruker, 2001); cell refinement: SAINT (Bruker, 2001); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ZORTEP (Zsolnai, 1997) and PLATON (Spek, 2003); software used to prepare material for publication: SHELXL97 and PARST (Nardelli, 1995).

1'-Methyl-4'-phenyl-9H-fluorene-9-spiro-3'-pyrrolidine-2'-spiro-3''- 1H-indol-2''(3''H)-one top
Crystal data top
C30H24N2OF(000) = 1808
Mr = 428.51Dx = 1.244 Mg m3
Orthorhombic, PbcaMo Kα radiation, λ = 0.71073 Å
Hall symbol: -P2ac2abCell parameters from 2136 reflections
a = 18.1752 (1) Åθ = 2.5–27.9°
b = 13.6193 (9) ŵ = 0.08 mm1
c = 18.4870 (1) ÅT = 273 K
V = 4576.2 (5) Å3Block, colourless
Z = 80.30 × 0.25 × 0.20 mm
Data collection top
Bruker SMART APEX
diffractometer
2700 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tubeRint = 0.063
Graphite monochromatorθmax = 25.0°, θmin = 2.2°
ω scansh = 2121
22067 measured reflectionsk = 1416
4023 independent reflectionsl = 2121
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)] = 0.081Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.179H-atom parameters constrained
S = 1.12 w = 1/[σ2(Fo2) + (0.0575P)2 + 2.8984P]
where P = (Fo2 + 2Fc2)/3
4023 reflections(Δ/σ)max < 0.001
298 parametersΔρmax = 0.23 e Å3
0 restraintsΔρmin = 0.19 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
C30.15644 (16)0.1416 (2)0.35954 (15)0.0410 (8)
C230.16409 (16)0.2063 (3)0.29270 (17)0.0478 (8)
C220.19693 (18)0.1848 (3)0.22743 (18)0.0625 (11)
H220.21910.12430.21940.075*
C210.1958 (2)0.2576 (4)0.1732 (2)0.0802 (14)
H210.21850.24610.12890.096*
C200.1608 (3)0.3462 (4)0.1859 (3)0.0902 (16)
H200.15940.39290.14930.108*
C190.1288 (2)0.3666 (3)0.2499 (2)0.0782 (13)
H190.10540.42650.25700.094*
C180.13100 (19)0.2977 (3)0.3051 (2)0.0548 (9)
C170.10603 (19)0.3029 (3)0.3795 (2)0.0554 (9)
C160.0724 (3)0.3782 (3)0.4175 (3)0.0827 (13)
H160.06000.43660.39440.099*
C150.0577 (3)0.3654 (4)0.4896 (3)0.0973 (17)
H150.03420.41500.51540.117*
C140.0771 (2)0.2806 (4)0.5237 (2)0.0810 (13)
H140.06730.27360.57280.097*
C130.11108 (19)0.2050 (3)0.48707 (18)0.0596 (10)
H130.12440.14780.51130.072*
C120.12516 (16)0.2150 (2)0.41394 (17)0.0448 (8)
C20.23068 (17)0.0846 (3)0.37573 (17)0.0515 (9)
H20.26510.10820.33880.062*
C10.21533 (19)0.0208 (3)0.3550 (2)0.0653 (11)
H1A0.25660.04850.32860.078*
H1B0.20630.06050.39760.078*
N10.14934 (15)0.0165 (2)0.30886 (15)0.0531 (7)
C40.10090 (16)0.0546 (2)0.34206 (15)0.0398 (8)
C110.06369 (18)0.0205 (2)0.41344 (18)0.0453 (8)
N20.00775 (14)0.0457 (2)0.41049 (14)0.0503 (7)
H10.03800.03900.44590.060*
C100.02702 (17)0.0843 (2)0.34297 (16)0.0413 (8)
C90.09529 (18)0.1153 (2)0.31996 (19)0.0514 (9)
H90.13540.11720.35120.062*
C80.1014 (2)0.1435 (3)0.2486 (2)0.0578 (9)
H80.14650.16610.23160.069*
C70.04281 (19)0.1392 (3)0.20212 (19)0.0568 (10)
H70.04920.15590.15380.068*
C60.02596 (18)0.1099 (2)0.22665 (17)0.0498 (9)
H60.06590.10780.19520.060*
C50.03425 (16)0.0841 (2)0.29841 (16)0.0393 (7)
C240.26949 (18)0.1039 (3)0.44684 (18)0.0563 (10)
C290.2717 (3)0.0386 (4)0.5029 (2)0.0909 (15)
H290.24560.01990.49940.109*
C280.3124 (3)0.0580 (5)0.5657 (3)0.1093 (19)
H280.31260.01340.60380.131*
C270.3520 (3)0.1435 (6)0.5702 (3)0.120 (2)
H270.38010.15640.61120.144*
C260.3502 (3)0.2092 (5)0.5152 (3)0.1124 (19)
H260.37700.26730.51830.135*
C250.3087 (2)0.1895 (4)0.4546 (2)0.0834 (13)
H250.30710.23580.41760.100*
C320.1168 (2)0.1114 (3)0.2938 (2)0.0838 (13)
H32A0.15300.15340.27210.126*
H32B0.07610.10330.26130.126*
H32C0.09990.14030.33820.126*
O10.09427 (12)0.02125 (18)0.46398 (12)0.0613 (7)
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
C30.0384 (17)0.0452 (19)0.0395 (17)0.0000 (15)0.0024 (14)0.0090 (15)
C230.0368 (18)0.063 (2)0.0439 (19)0.0163 (17)0.0057 (15)0.0080 (17)
C220.045 (2)0.096 (3)0.047 (2)0.018 (2)0.0020 (17)0.017 (2)
C210.063 (3)0.127 (4)0.051 (2)0.034 (3)0.004 (2)0.025 (3)
C200.096 (4)0.095 (4)0.079 (3)0.038 (3)0.025 (3)0.043 (3)
C190.096 (3)0.062 (3)0.077 (3)0.024 (2)0.032 (3)0.029 (2)
C180.055 (2)0.043 (2)0.066 (2)0.0150 (18)0.0211 (18)0.0121 (19)
C170.056 (2)0.048 (2)0.062 (2)0.0033 (18)0.0219 (18)0.0020 (19)
C160.105 (3)0.047 (3)0.096 (4)0.024 (2)0.030 (3)0.010 (2)
C150.115 (4)0.091 (4)0.085 (3)0.046 (3)0.027 (3)0.037 (3)
C140.085 (3)0.101 (4)0.057 (2)0.034 (3)0.012 (2)0.025 (3)
C130.060 (2)0.068 (3)0.051 (2)0.016 (2)0.0044 (17)0.0068 (19)
C120.0398 (18)0.048 (2)0.0470 (19)0.0007 (15)0.0073 (15)0.0013 (16)
C20.0386 (18)0.065 (2)0.051 (2)0.0106 (17)0.0098 (15)0.0127 (18)
C10.054 (2)0.074 (3)0.068 (2)0.030 (2)0.0124 (19)0.002 (2)
N10.0567 (17)0.0439 (18)0.0587 (17)0.0111 (14)0.0106 (14)0.0046 (14)
C40.0422 (18)0.0374 (18)0.0396 (17)0.0041 (14)0.0097 (14)0.0036 (14)
C110.0457 (19)0.0399 (19)0.050 (2)0.0011 (16)0.0080 (16)0.0097 (16)
N20.0396 (16)0.0603 (19)0.0510 (16)0.0001 (13)0.0150 (13)0.0114 (14)
C100.0421 (19)0.0349 (18)0.0469 (18)0.0044 (15)0.0025 (15)0.0013 (15)
C90.0398 (19)0.051 (2)0.063 (2)0.0011 (16)0.0015 (17)0.0044 (18)
C80.046 (2)0.053 (2)0.074 (3)0.0047 (18)0.0169 (19)0.000 (2)
C70.059 (2)0.060 (2)0.051 (2)0.0134 (19)0.0168 (18)0.0063 (18)
C60.051 (2)0.052 (2)0.047 (2)0.0096 (17)0.0023 (16)0.0003 (16)
C50.0421 (18)0.0299 (17)0.0460 (18)0.0039 (14)0.0018 (14)0.0005 (14)
C240.039 (2)0.082 (3)0.047 (2)0.019 (2)0.0061 (16)0.011 (2)
C290.090 (3)0.115 (4)0.068 (3)0.024 (3)0.008 (2)0.023 (3)
C280.109 (4)0.151 (6)0.068 (3)0.048 (4)0.016 (3)0.025 (4)
C270.079 (4)0.198 (7)0.082 (4)0.028 (4)0.016 (3)0.023 (5)
C260.095 (4)0.159 (6)0.084 (4)0.019 (4)0.004 (3)0.038 (4)
C250.076 (3)0.106 (4)0.068 (3)0.010 (3)0.004 (2)0.003 (3)
C320.105 (3)0.054 (3)0.093 (3)0.015 (2)0.002 (3)0.014 (2)
O10.0541 (14)0.0723 (17)0.0573 (15)0.0115 (13)0.0140 (12)0.0296 (13)
Geometric parameters (Å, º) top
C3—C231.524 (4)N1—C321.447 (4)
C3—C121.527 (4)C4—C51.510 (4)
C3—C21.585 (4)C4—C111.554 (4)
C3—C41.590 (4)C11—O11.227 (4)
C23—C221.377 (4)C11—N21.344 (4)
C23—C181.402 (5)N2—C101.399 (4)
C22—C211.410 (5)N2—H10.8600
C22—H220.9300C10—C91.378 (4)
C21—C201.384 (6)C10—C51.385 (4)
C21—H210.9300C9—C81.378 (5)
C20—C191.347 (6)C9—H90.9300
C20—H200.9300C8—C71.370 (5)
C19—C181.386 (5)C8—H80.9300
C19—H190.9300C7—C61.388 (4)
C18—C171.451 (5)C7—H70.9300
C17—C161.385 (5)C6—C51.381 (4)
C17—C121.400 (4)C6—H60.9300
C16—C151.370 (6)C24—C291.366 (5)
C16—H160.9300C24—C251.374 (6)
C15—C141.363 (6)C29—C281.401 (7)
C15—H150.9300C29—H290.9300
C14—C131.379 (5)C28—C271.372 (8)
C14—H140.9300C28—H280.9300
C13—C121.383 (4)C27—C261.356 (8)
C13—H130.9300C27—H270.9300
C2—C11.512 (5)C26—C251.377 (6)
C2—C241.515 (5)C26—H260.9300
C2—H20.9800C25—H250.9300
C1—N11.473 (4)C32—H32A0.9600
C1—H1A0.9700C32—H32B0.9600
C1—H1B0.9700C32—H32C0.9600
N1—C41.446 (4)
C23—C3—C12101.0 (3)C32—N1—C1114.1 (3)
C23—C3—C2111.0 (2)N1—C4—C5116.1 (3)
C12—C3—C2120.9 (3)N1—C4—C11115.2 (2)
C23—C3—C4108.9 (2)C5—C4—C11100.6 (2)
C12—C3—C4112.7 (2)N1—C4—C3101.5 (2)
C2—C3—C4102.3 (2)C5—C4—C3114.8 (2)
C22—C23—C18121.1 (3)C11—C4—C3109.0 (2)
C22—C23—C3128.9 (3)O1—C11—N2125.9 (3)
C18—C23—C3110.0 (3)O1—C11—C4126.0 (3)
C23—C22—C21117.9 (4)N2—C11—C4108.1 (3)
C23—C22—H22121.1C11—N2—C10112.0 (3)
C21—C22—H22121.1C11—N2—H1124.0
C20—C21—C22119.9 (4)C10—N2—H1124.0
C20—C21—H21120.1C9—C10—C5122.7 (3)
C22—C21—H21120.1C9—C10—N2128.0 (3)
C19—C20—C21121.8 (4)C5—C10—N2109.2 (3)
C19—C20—H20119.1C8—C9—C10117.0 (3)
C21—C20—H20119.1C8—C9—H9121.5
C20—C19—C18119.6 (5)C10—C9—H9121.5
C20—C19—H19120.2C7—C8—C9121.7 (3)
C18—C19—H19120.2C7—C8—H8119.1
C19—C18—C23119.6 (4)C9—C8—H8119.1
C19—C18—C17131.0 (4)C8—C7—C6120.5 (3)
C23—C18—C17109.4 (3)C8—C7—H7119.8
C16—C17—C12120.8 (4)C6—C7—H7119.8
C16—C17—C18130.9 (4)C5—C6—C7119.0 (3)
C12—C17—C18108.2 (3)C5—C6—H6120.5
C15—C16—C17119.0 (4)C7—C6—H6120.5
C15—C16—H16120.5C6—C5—C10118.9 (3)
C17—C16—H16120.5C6—C5—C4132.0 (3)
C14—C15—C16120.5 (4)C10—C5—C4109.1 (3)
C14—C15—H15119.8C29—C24—C25117.3 (4)
C16—C15—H15119.8C29—C24—C2124.1 (4)
C15—C14—C13121.5 (4)C25—C24—C2118.6 (3)
C15—C14—H14119.3C24—C29—C28121.4 (5)
C13—C14—H14119.3C24—C29—H29119.3
C14—C13—C12119.3 (4)C28—C29—H29119.3
C14—C13—H13120.3C27—C28—C29119.2 (5)
C12—C13—H13120.3C27—C28—H28120.4
C13—C12—C17118.9 (3)C29—C28—H28120.4
C13—C12—C3130.4 (3)C26—C27—C28120.2 (6)
C17—C12—C3110.6 (3)C26—C27—H27119.9
C1—C2—C24118.1 (3)C28—C27—H27119.9
C1—C2—C3105.1 (3)C27—C26—C25119.7 (6)
C24—C2—C3118.4 (3)C27—C26—H26120.2
C1—C2—H2104.6C25—C26—H26120.2
C24—C2—H2104.6C24—C25—C26122.3 (5)
C3—C2—H2104.6C24—C25—H25118.9
N1—C1—C2105.1 (3)C26—C25—H25118.9
N1—C1—H1A110.7N1—C32—H32A109.5
C2—C1—H1A110.7N1—C32—H32B109.5
N1—C1—H1B110.7H32A—C32—H32B109.5
C2—C1—H1B110.7N1—C32—H32C109.5
H1A—C1—H1B108.8H32A—C32—H32C109.5
C4—N1—C32115.5 (3)H32B—C32—H32C109.5
C4—N1—C1106.1 (3)
C12—C3—C23—C22172.3 (3)C1—N1—C4—C1172.1 (3)
C2—C3—C23—C2242.9 (4)C32—N1—C4—C3172.9 (3)
C4—C3—C23—C2269.0 (4)C1—N1—C4—C345.5 (3)
C12—C3—C23—C188.2 (3)C23—C3—C4—N185.2 (3)
C2—C3—C23—C18137.5 (3)C12—C3—C4—N1163.7 (2)
C4—C3—C23—C18110.6 (3)C2—C3—C4—N132.3 (3)
C18—C23—C22—C210.4 (5)C23—C3—C4—C540.8 (3)
C3—C23—C22—C21179.1 (3)C12—C3—C4—C570.3 (3)
C23—C22—C21—C201.6 (5)C2—C3—C4—C5158.4 (2)
C22—C21—C20—C191.6 (6)C23—C3—C4—C11152.8 (3)
C21—C20—C19—C180.4 (6)C12—C3—C4—C1141.7 (3)
C20—C19—C18—C232.3 (5)C2—C3—C4—C1189.6 (3)
C20—C19—C18—C17175.2 (4)N1—C4—C11—O145.4 (5)
C22—C23—C18—C192.4 (5)C5—C4—C11—O1171.1 (3)
C3—C23—C18—C19177.2 (3)C3—C4—C11—O167.8 (4)
C22—C23—C18—C17175.7 (3)N1—C4—C11—N2135.2 (3)
C3—C23—C18—C174.8 (4)C5—C4—C11—N29.5 (3)
C19—C18—C17—C160.2 (7)C3—C4—C11—N2111.6 (3)
C23—C18—C17—C16178.0 (4)O1—C11—N2—C10174.6 (3)
C19—C18—C17—C12176.5 (4)C4—C11—N2—C106.1 (4)
C23—C18—C17—C121.3 (4)C11—N2—C10—C9178.2 (3)
C12—C17—C16—C150.3 (6)C11—N2—C10—C50.6 (4)
C18—C17—C16—C15176.6 (4)C5—C10—C9—C82.3 (5)
C17—C16—C15—C141.3 (7)N2—C10—C9—C8175.0 (3)
C16—C15—C14—C130.9 (7)C10—C9—C8—C71.3 (5)
C15—C14—C13—C120.5 (6)C9—C8—C7—C62.9 (5)
C14—C13—C12—C171.5 (5)C8—C7—C6—C50.8 (5)
C14—C13—C12—C3175.1 (3)C7—C6—C5—C102.6 (5)
C16—C17—C12—C131.1 (5)C7—C6—C5—C4176.5 (3)
C18—C17—C12—C13176.0 (3)C9—C10—C5—C64.3 (5)
C16—C17—C12—C3176.1 (3)N2—C10—C5—C6173.5 (3)
C18—C17—C12—C36.8 (4)C9—C10—C5—C4175.0 (3)
C23—C3—C12—C13174.1 (3)N2—C10—C5—C47.2 (3)
C2—C3—C12—C1351.4 (5)N1—C4—C5—C645.9 (5)
C4—C3—C12—C1369.9 (4)C11—C4—C5—C6170.9 (3)
C23—C3—C12—C179.0 (3)C3—C4—C5—C672.2 (4)
C2—C3—C12—C17131.8 (3)N1—C4—C5—C10134.9 (3)
C4—C3—C12—C17106.9 (3)C11—C4—C5—C109.9 (3)
C23—C3—C2—C1107.2 (3)C3—C4—C5—C10107.0 (3)
C12—C3—C2—C1135.0 (3)C1—C2—C24—C2920.9 (5)
C4—C3—C2—C18.9 (3)C3—C2—C24—C29107.6 (4)
C23—C3—C2—C24118.4 (3)C1—C2—C24—C25155.1 (3)
C12—C3—C2—C240.6 (4)C3—C2—C24—C2576.3 (4)
C4—C3—C2—C24125.5 (3)C25—C24—C29—C280.2 (6)
C24—C2—C1—N1152.0 (3)C2—C24—C29—C28175.9 (4)
C3—C2—C1—N117.5 (3)C24—C29—C28—C271.3 (8)
C2—C1—N1—C440.7 (3)C29—C28—C27—C261.5 (9)
C2—C1—N1—C32169.0 (3)C28—C27—C26—C250.2 (9)
C32—N1—C4—C561.9 (4)C29—C24—C25—C261.5 (6)
C1—N1—C4—C5170.7 (3)C2—C24—C25—C26174.8 (4)
C32—N1—C4—C1155.3 (4)C27—C26—C25—C241.4 (8)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
C1—H1B···O10.972.432.983 (4)115
C13—H13···O10.932.533.126 (5)122
N2—H1···O1i0.861.972.823 (3)171
C6—H6···CgB0.933.003.376 (3)105
C19—H19···CgAii0.932.893.790 (4)161
Symmetry codes: (i) x, y, z+1; (ii) x, y+1/2, z+1/2.
 

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