6-Bromo-9,9-diethyl-N,N-di­phenyl­fluoren-2-amine

Themmila Khamrang; A Kannan; C Ponraj; Madhukar Hemamalini; G Jerald Maria Antony; Dhandayutham Saravanan

doi:10.1107/S2414314624011763

. 2024 Dec 20;9(Pt 12):x241176. doi: 10.1107/S2414314624011763

6-Bromo-9,9-diethyl-N,N-diphenylfluoren-2-amine

Themmila Khamrang ^a, A Kannan ^b, C Ponraj ^c, Madhukar Hemamalini ^d, G Jerald Maria Antony ^c,^*, Dhandayutham Saravanan ^c

Editor: W T A Harrison^e

PMCID: PMC11701759 PMID: 39777005

In the title compound, the dihedral angles between the fluorene fused-ring system and the pendant phenyl groups are 67.76 (12) and 88.38 (12)°. In the crystal, weak pairwise C—H⋯π interactions link the molecules into inversion dimers.

Keywords: crystal structure, C—H⋯π interactions

Abstract

In the title compound, C₂₉H₂₆BrN, the dihedral angles between the fluorene fused-ring system and the pendant phenyl groups are 67.76 (12) and 88.38 (12)°. In the crystal, weak pairwise C—H⋯π interactions link the molecules into inversion dimers.

Structure description

Some fluoren-9-imines show fluorescence properties (Dufresne et al., 2011 ▸) and potential as organic components in materials with flexible HOMO–LUMO gaps (Eakins et al., 2013 ▸). The crystal structures of N-mesityl-9H-fluoren-9-imine (Evans et al., 2016 ▸), N-(4-chlorophenyl)-9H-fluoren-9-imine (Crundwell et al., 2019 ▸), 9-(4-bromobutyl)-9H-fluorene-9-carboxylic acid (Zhang et al., 2014 ▸) and 9,9-diethyl-9H-fluorene-2,4,7-tricarbaldehyde (Seidel et al., 2021 ▸) have been reported. As part of our research in this field, we present the synthesis and structural characterization of the title compound, C₂₉H₂₆BrN, (I).

The asymmetric unit of (I) contains one molecule (Fig. 1 ▸) in space group P2₁/c. The dihedral angles between the C13–C25 fluorene fused ring (r.m.s. deviation = 0.030 Å) and the pendant C1–C6 and C7–C12 phenyl groups are 67.76 (12) and 88.38 (12)°, respectively; the dihedral angle between the phenyl groups is 60.96 (16)°. The packing of the crystal structure is illustrated in Fig. 2 ▸. Neighboring molecules within the structure are linked by pairwise C—H⋯π interactions, as detailed in Table 1 ▸.

The asymmetric unit of (I). Displacement ellipsoids are drawn at the 50% probability level.

Table 1. Hydrogen-bond geometry (Å, °).

Cg5 is the centroid of the C17–C22 ring.

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C2—H19⋯Cg5ⁱ	0.93	2.87	3.692 (4)	148

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Symmetry code: (i) Inline graphic .

A search of the Cambridge Structural Database (Version 5.43, update November 2022; Groom et al., 2016 ▸) for the fluoren-9-imine fragment with additional substituents yielded 9H-fluoren-9-imine (CSD refcode EPAJEN: Kent et al., 2021 ▸), N-[(2-nitrophenyl)sulfanyl]-9H-fluoren-9-imine (REQXUI: Melen et al., 2013 ▸), N-hydroxy-9H-fluoren-9-imine (NIXWUO: Bugenhagen et al., 2014 ▸), and N,N′-([1,1′-biphenyl]-4,4′-diyl)bis(9H-fluoren-9-imine) (LODQEE: Sprachmann et al., 2023 ▸).

Synthesis and crystallization

The title compound was prepared by the literature method (Thomas et al., 2005 ▸). Crystals suitable for X-ray diffraction were grown by recrystallization from dichloromethane solution.

Refinement

Crystal data, data collection and structure refinement details are summarized in Table 2 ▸.

Table 2. Experimental details.

Crystal data
Chemical formula	C₂₉H₂₆BrN
M _r	468.42
Crystal system, space group	Monoclinic, P2₁/c
Temperature (K)	293
a, b, c (Å)	12.7044 (14), 10.5123 (17), 18.2491 (19)
β (°)	105.372 (12)
V (Å³)	2350.0 (5)
Z	4
Radiation type	Mo Kα
μ (mm⁻¹)	1.77
Crystal size (mm)	0.37 × 0.32 × 0.29

Data collection
Diffractometer	Agilent Xcalibur, Atlas, Gemini
Absorption correction	Multi-scan (CrysAlis RED; Agilent, 2012 ▸)
T_min, T_max	0.507, 0.578
No. of measured, independent and observed [I > 2σ(I)] reflections	8476, 4762, 2977
R _int	0.029
(sin θ/λ)_max (Å⁻¹)	0.625

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.048, 0.117, 1.02
No. of reflections	4762
No. of parameters	282
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.54, −0.60

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Computer programs: CrysAlis PRO (Agilent, 2012 ▸), SHELXT2018/2 (Sheldrick, 2015a ▸), SHELXL2018/3 (Sheldrick, 2015b ▸) and PLATON (Spek, 2020 ▸).

Supplementary Material

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S2414314624011763/hb4495sup1.cif

x-09-x241176-sup1.cif^{(339.8KB, cif)}

Structure factors: contains datablock(s) I. DOI: 10.1107/S2414314624011763/hb4495Isup2.hkl

x-09-x241176-Isup2.hkl^{(379.2KB, hkl)}

x-09-x241176-Isup3.cml^{(8.3KB, cml)}

Supporting information file. DOI: 10.1107/S2414314624011763/hb4495Isup3.cml

CCDC reference: 2407284

Additional supporting information: crystallographic information; 3D view; checkCIF report

full crystallographic data

6-Bromo-9,9-diethyl-N,N-diphenylfluoren-2-amine . Crystal data

C₂₉H₂₆BrN	F(000) = 968
M_r = 468.42	D_x = 1.324 Mg m⁻³
Monoclinic, P2₁/c	Mo Kα radiation, λ = 0.71073 Å
a = 12.7044 (14) Å	Cell parameters from 9567 reflections
b = 10.5123 (17) Å	θ = 3.6–26.5°
c = 18.2491 (19) Å	µ = 1.77 mm⁻¹
β = 105.372 (12)°	T = 293 K
V = 2350.0 (5) Å³	Plate, colourless
Z = 4	0.37 × 0.32 × 0.28 mm

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6-Bromo-9,9-diethyl-N,N-diphenylfluoren-2-amine . Data collection

Agilent Xcalibur, Atlas, Gemini diffractometer	2977 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	R_int = 0.029
ω scans	θ_max = 26.4°, θ_min = 3.5°
Absorption correction: multi-scan (CrysAlis RED; Agilent, 2012)	h = −9→15
T_min = 0.507, T_max = 0.578	k = −13→6
8476 measured reflections	l = −20→22
4762 independent reflections

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6-Bromo-9,9-diethyl-N,N-diphenylfluoren-2-amine . Refinement

Refinement on F²	Primary atom site location: dual
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F² > 2σ(F²)] = 0.048	H-atom parameters constrained
wR(F²) = 0.117	w = 1/[σ²(F_o²) + (0.0391P)² + 1.125P] where P = (F_o² + 2F_c²)/3
S = 1.02	(Δ/σ)_max = 0.001
4762 reflections	Δρ_max = 0.54 e Å⁻³
282 parameters	Δρ_min = −0.60 e Å⁻³
0 restraints

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6-Bromo-9,9-diethyl-N,N-diphenylfluoren-2-amine . Special details

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. All the H atoms were positioned geometrically (C—H = 0.93–0.97 Å) and were refined using a riding model, with U_iso(H) = 1.2 U_eq(C).

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6-Bromo-9,9-diethyl-N,N-diphenylfluoren-2-amine . Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å²)

	x	y	z	U_iso*/U_eq
Br1	0.95429 (3)	0.61601 (5)	0.10095 (2)	0.0858 (2)
N1	0.6358 (2)	0.3480 (3)	0.52774 (13)	0.0483 (7)
C6	0.6913 (2)	0.4055 (3)	0.59604 (15)	0.0397 (7)
C12	0.5429 (2)	0.2704 (3)	0.52127 (15)	0.0403 (7)
C5	0.6402 (2)	0.4278 (3)	0.65293 (16)	0.0457 (8)
H16	0.567720	0.403893	0.646045	0.055*
C25	0.6902 (2)	0.4777 (3)	0.43321 (15)	0.0425 (7)
H2	0.668430	0.550728	0.453992	0.051*
C1	0.7982 (2)	0.4448 (3)	0.60737 (16)	0.0462 (8)
H20	0.833360	0.432118	0.569297	0.055*
C24	0.7358 (2)	0.4858 (3)	0.37282 (15)	0.0389 (7)
C16	0.7665 (2)	0.3769 (3)	0.34112 (15)	0.0417 (7)
C4	0.6958 (3)	0.4849 (3)	0.71935 (17)	0.0510 (8)
H17	0.660812	0.498929	0.757410	0.061*
C22	0.8134 (2)	0.5466 (3)	0.27537 (15)	0.0415 (7)
C17	0.8142 (2)	0.4145 (3)	0.27948 (16)	0.0429 (7)
C23	0.7604 (2)	0.6046 (3)	0.33320 (15)	0.0420 (7)
C21	0.8555 (2)	0.6077 (3)	0.22258 (16)	0.0489 (8)
H6	0.856900	0.696032	0.220138	0.059*
C7	0.5403 (2)	0.1756 (3)	0.57312 (17)	0.0502 (8)
H22	0.600767	0.161627	0.614011	0.060*
C13	0.6774 (2)	0.3589 (3)	0.46244 (16)	0.0439 (7)
C26	0.6551 (3)	0.6756 (3)	0.29330 (19)	0.0572 (9)
H30A	0.620478	0.704973	0.331615	0.069*
H30B	0.674493	0.750156	0.268381	0.069*
C11	0.4529 (3)	0.2877 (3)	0.46116 (17)	0.0525 (8)
H26	0.453256	0.350736	0.425475	0.063*
C3	0.8025 (3)	0.5218 (3)	0.73041 (19)	0.0550 (9)
H18	0.840137	0.559872	0.775801	0.066*
C14	0.7071 (3)	0.2511 (3)	0.43068 (17)	0.0538 (9)
H13	0.697315	0.171879	0.450604	0.065*
C2	0.8527 (3)	0.5018 (3)	0.67364 (18)	0.0530 (8)
H19	0.924772	0.527292	0.680377	0.064*
C15	0.7516 (3)	0.2588 (3)	0.36916 (18)	0.0534 (8)
H12	0.770937	0.185547	0.347291	0.064*
C28	0.8353 (3)	0.6960 (3)	0.38836 (18)	0.0554 (9)
H28A	0.853799	0.765901	0.359389	0.066*
H28B	0.795045	0.731182	0.421969	0.066*
C18	0.8542 (3)	0.3425 (3)	0.22966 (17)	0.0538 (9)
H9	0.853886	0.254087	0.232049	0.065*
C20	0.8952 (2)	0.5344 (4)	0.17374 (16)	0.0534 (9)
C19	0.8947 (3)	0.4046 (4)	0.17605 (17)	0.0594 (10)
H8	0.921608	0.357949	0.141644	0.071*
C10	0.3627 (3)	0.2128 (4)	0.4534 (2)	0.0614 (10)
H25	0.302388	0.225092	0.412174	0.074*
C8	0.4492 (3)	0.1026 (3)	0.5645 (2)	0.0616 (9)
H23	0.448149	0.039306	0.599897	0.074*
C9	0.3599 (3)	0.1205 (4)	0.5050 (2)	0.0631 (10)
H24	0.297871	0.070585	0.499736	0.076*
C27	0.5732 (3)	0.5986 (4)	0.2352 (2)	0.0750 (12)
H31A	0.603564	0.576906	0.193923	0.112*
H31B	0.507957	0.647711	0.216245	0.112*
H31C	0.556058	0.522199	0.258433	0.112*
C29	0.9385 (3)	0.6393 (4)	0.4357 (2)	0.0774 (12)
H29A	0.974601	0.593977	0.403666	0.116*
H29B	0.922103	0.581655	0.471999	0.116*
H29C	0.985418	0.705712	0.462089	0.116*

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6-Bromo-9,9-diethyl-N,N-diphenylfluoren-2-amine . Atomic displacement parameters (Å²)

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Br1	0.0712 (3)	0.1406 (5)	0.0560 (2)	−0.0011 (3)	0.03493 (19)	0.0268 (2)
N1	0.0527 (15)	0.0639 (18)	0.0314 (13)	−0.0212 (14)	0.0167 (11)	−0.0053 (12)
C6	0.0426 (16)	0.0447 (18)	0.0320 (14)	−0.0033 (15)	0.0100 (12)	0.0057 (14)
C12	0.0406 (15)	0.0489 (19)	0.0327 (15)	−0.0046 (15)	0.0121 (12)	−0.0013 (14)
C5	0.0433 (16)	0.056 (2)	0.0402 (16)	−0.0045 (16)	0.0147 (13)	0.0002 (15)
C25	0.0476 (17)	0.0478 (19)	0.0346 (15)	−0.0043 (16)	0.0155 (13)	−0.0045 (14)
C1	0.0435 (16)	0.058 (2)	0.0377 (16)	−0.0037 (16)	0.0123 (13)	0.0026 (15)
C24	0.0422 (16)	0.0428 (18)	0.0326 (14)	−0.0032 (15)	0.0114 (12)	0.0000 (14)
C16	0.0496 (17)	0.0450 (19)	0.0338 (15)	−0.0045 (16)	0.0167 (13)	−0.0039 (14)
C4	0.064 (2)	0.051 (2)	0.0419 (17)	0.0019 (18)	0.0213 (15)	−0.0049 (16)
C22	0.0375 (15)	0.056 (2)	0.0310 (14)	−0.0012 (16)	0.0099 (12)	0.0033 (14)
C17	0.0428 (16)	0.055 (2)	0.0339 (15)	−0.0055 (16)	0.0153 (13)	−0.0044 (15)
C23	0.0485 (17)	0.0449 (18)	0.0355 (15)	−0.0003 (16)	0.0162 (13)	0.0021 (14)
C21	0.0434 (16)	0.067 (2)	0.0377 (16)	−0.0026 (17)	0.0133 (13)	0.0083 (16)
C7	0.0452 (18)	0.056 (2)	0.0460 (18)	−0.0095 (17)	0.0069 (14)	0.0107 (16)
C13	0.0485 (17)	0.053 (2)	0.0332 (15)	−0.0129 (16)	0.0153 (13)	−0.0025 (14)
C26	0.058 (2)	0.060 (2)	0.058 (2)	0.0127 (19)	0.0254 (17)	0.0139 (18)
C11	0.0548 (19)	0.060 (2)	0.0405 (17)	−0.0001 (18)	0.0084 (15)	0.0087 (16)
C3	0.064 (2)	0.049 (2)	0.0468 (18)	−0.0053 (19)	0.0054 (16)	−0.0097 (16)
C14	0.074 (2)	0.0434 (19)	0.0515 (19)	−0.0135 (18)	0.0290 (17)	0.0006 (16)
C2	0.0447 (17)	0.059 (2)	0.052 (2)	−0.0061 (17)	0.0069 (15)	0.0015 (17)
C15	0.072 (2)	0.0405 (19)	0.0551 (19)	−0.0057 (18)	0.0306 (17)	−0.0086 (16)
C28	0.067 (2)	0.051 (2)	0.0523 (19)	−0.0091 (19)	0.0234 (17)	−0.0034 (17)
C18	0.0571 (19)	0.062 (2)	0.0465 (18)	−0.0045 (18)	0.0215 (15)	−0.0113 (17)
C20	0.0428 (17)	0.087 (3)	0.0330 (16)	−0.002 (2)	0.0141 (13)	0.0087 (18)
C19	0.0536 (19)	0.091 (3)	0.0381 (17)	−0.003 (2)	0.0211 (15)	−0.0135 (19)
C10	0.0425 (18)	0.078 (3)	0.056 (2)	0.000 (2)	0.0001 (15)	−0.009 (2)
C8	0.064 (2)	0.059 (2)	0.064 (2)	−0.014 (2)	0.0204 (18)	0.0081 (19)
C9	0.0455 (19)	0.070 (3)	0.074 (2)	−0.0159 (19)	0.0153 (18)	−0.012 (2)
C27	0.050 (2)	0.115 (3)	0.058 (2)	0.007 (2)	0.0118 (17)	0.004 (2)
C29	0.059 (2)	0.100 (3)	0.068 (2)	−0.005 (2)	0.0079 (19)	−0.018 (2)

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6-Bromo-9,9-diethyl-N,N-diphenylfluoren-2-amine . Geometric parameters (Å, º)

Br1—C20	1.896 (3)	C13—C14	1.371 (4)
N1—C6	1.397 (4)	C26—C27	1.509 (5)
N1—C12	1.413 (4)	C26—H30A	0.9700
N1—C13	1.431 (3)	C26—H30B	0.9700
C6—C1	1.381 (4)	C11—C10	1.367 (4)
C6—C5	1.383 (4)	C11—H26	0.9300
C12—C11	1.371 (4)	C3—C2	1.370 (4)
C12—C7	1.380 (4)	C3—H18	0.9300
C5—C4	1.369 (4)	C14—C15	1.387 (4)
C5—H16	0.9300	C14—H13	0.9300
C25—C24	1.376 (4)	C2—H19	0.9300
C25—C13	1.385 (4)	C15—H12	0.9300
C25—H2	0.9300	C28—C29	1.491 (5)
C1—C2	1.363 (4)	C28—H28A	0.9700
C1—H20	0.9300	C28—H28B	0.9700
C24—C16	1.385 (4)	C18—C19	1.384 (4)
C24—C23	1.517 (4)	C18—H9	0.9300
C16—C15	1.375 (4)	C20—C19	1.365 (5)
C16—C17	1.466 (4)	C19—H8	0.9300
C4—C3	1.373 (4)	C10—C9	1.359 (5)
C4—H17	0.9300	C10—H25	0.9300
C22—C21	1.378 (4)	C8—C9	1.360 (5)
C22—C17	1.391 (4)	C8—H23	0.9300
C22—C23	1.522 (4)	C9—H24	0.9300
C17—C18	1.380 (4)	C27—H31A	0.9600
C23—C28	1.527 (4)	C27—H31B	0.9600
C23—C26	1.536 (4)	C27—H31C	0.9600
C21—C20	1.372 (4)	C29—H29A	0.9600
C21—H6	0.9300	C29—H29B	0.9600
C7—C8	1.363 (4)	C29—H29C	0.9600
C7—H22	0.9300

C6—N1—C12	122.5 (2)	H30A—C26—H30B	107.5
C6—N1—C13	119.9 (2)	C10—C11—C12	120.3 (3)
C12—N1—C13	117.5 (2)	C10—C11—H26	119.8
C1—C6—C5	118.4 (3)	C12—C11—H26	119.8
C1—C6—N1	120.5 (2)	C2—C3—C4	119.0 (3)
C5—C6—N1	121.1 (3)	C2—C3—H18	120.5
C11—C12—C7	118.5 (3)	C4—C3—H18	120.5
C11—C12—N1	119.4 (3)	C13—C14—C15	120.7 (3)
C7—C12—N1	122.1 (3)	C13—C14—H13	119.6
C4—C5—C6	120.3 (3)	C15—C14—H13	119.6
C4—C5—H16	119.9	C1—C2—C3	120.6 (3)
C6—C5—H16	119.9	C1—C2—H19	119.7
C24—C25—C13	118.8 (3)	C3—C2—H19	119.7
C24—C25—H2	120.6	C16—C15—C14	118.7 (3)
C13—C25—H2	120.6	C16—C15—H12	120.6
C2—C1—C6	120.8 (3)	C14—C15—H12	120.6
C2—C1—H20	119.6	C29—C28—C23	115.4 (3)
C6—C1—H20	119.6	C29—C28—H28A	108.4
C25—C24—C16	120.6 (3)	C23—C28—H28A	108.4
C25—C24—C23	128.0 (3)	C29—C28—H28B	108.4
C16—C24—C23	111.4 (2)	C23—C28—H28B	108.4
C15—C16—C24	120.6 (3)	H28A—C28—H28B	107.5
C15—C16—C17	130.9 (3)	C17—C18—C19	118.5 (3)
C24—C16—C17	108.5 (3)	C17—C18—H9	120.7
C5—C4—C3	120.8 (3)	C19—C18—H9	120.7
C5—C4—H17	119.6	C19—C20—C21	122.4 (3)
C3—C4—H17	119.6	C19—C20—Br1	118.7 (3)
C21—C22—C17	120.3 (3)	C21—C20—Br1	118.9 (3)
C21—C22—C23	128.5 (3)	C20—C19—C18	119.9 (3)
C17—C22—C23	111.2 (2)	C20—C19—H8	120.0
C18—C17—C22	120.8 (3)	C18—C19—H8	120.0
C18—C17—C16	131.0 (3)	C9—C10—C11	121.0 (3)
C22—C17—C16	108.2 (3)	C9—C10—H25	119.5
C24—C23—C22	100.7 (2)	C11—C10—H25	119.5
C24—C23—C28	112.0 (2)	C9—C8—C7	121.2 (3)
C22—C23—C28	113.3 (2)	C9—C8—H23	119.4
C24—C23—C26	111.2 (2)	C7—C8—H23	119.4
C22—C23—C26	110.8 (2)	C10—C9—C8	118.8 (3)
C28—C23—C26	108.6 (3)	C10—C9—H24	120.6
C20—C21—C22	118.0 (3)	C8—C9—H24	120.6
C20—C21—H6	121.0	C26—C27—H31A	109.5
C22—C21—H6	121.0	C26—C27—H31B	109.5
C8—C7—C12	120.1 (3)	H31A—C27—H31B	109.5
C8—C7—H22	119.9	C26—C27—H31C	109.5
C12—C7—H22	119.9	H31A—C27—H31C	109.5
C14—C13—C25	120.6 (3)	H31B—C27—H31C	109.5
C14—C13—N1	119.3 (3)	C28—C29—H29A	109.5
C25—C13—N1	120.0 (3)	C28—C29—H29B	109.5
C27—C26—C23	115.1 (3)	H29A—C29—H29B	109.5
C27—C26—H30A	108.5	C28—C29—H29C	109.5
C23—C26—H30A	108.5	H29A—C29—H29C	109.5
C27—C26—H30B	108.5	H29B—C29—H29C	109.5
C23—C26—H30B	108.5

C12—N1—C6—C1	158.9 (3)	C17—C22—C23—C26	−115.5 (3)
C13—N1—C6—C1	−16.4 (4)	C17—C22—C21—C20	1.5 (4)
C12—N1—C6—C5	−22.9 (4)	C23—C22—C21—C20	−177.1 (3)
C13—N1—C6—C5	161.8 (3)	C11—C12—C7—C8	−0.7 (5)
C6—N1—C12—C11	133.9 (3)	N1—C12—C7—C8	−179.7 (3)
C13—N1—C12—C11	−50.7 (4)	C24—C25—C13—C14	−1.6 (4)
C6—N1—C12—C7	−47.1 (4)	C24—C25—C13—N1	176.6 (3)
C13—N1—C12—C7	128.2 (3)	C6—N1—C13—C14	118.5 (3)
C1—C6—C5—C4	−1.4 (5)	C12—N1—C13—C14	−57.0 (4)
N1—C6—C5—C4	−179.6 (3)	C6—N1—C13—C25	−59.7 (4)
C5—C6—C1—C2	1.3 (5)	C12—N1—C13—C25	124.8 (3)
N1—C6—C1—C2	179.5 (3)	C24—C23—C26—C27	−57.7 (3)
C13—C25—C24—C16	1.0 (4)	C22—C23—C26—C27	53.5 (4)
C13—C25—C24—C23	−178.2 (3)	C28—C23—C26—C27	178.6 (3)
C25—C24—C16—C15	0.4 (4)	C7—C12—C11—C10	0.3 (5)
C23—C24—C16—C15	179.7 (3)	N1—C12—C11—C10	179.3 (3)
C25—C24—C16—C17	−178.8 (3)	C5—C4—C3—C2	0.6 (5)
C23—C24—C16—C17	0.5 (3)	C25—C13—C14—C15	0.7 (5)
C6—C5—C4—C3	0.5 (5)	N1—C13—C14—C15	−177.5 (3)
C21—C22—C17—C18	−1.8 (5)	C6—C1—C2—C3	−0.2 (5)
C23—C22—C17—C18	177.1 (3)	C4—C3—C2—C1	−0.7 (5)
C21—C22—C17—C16	179.0 (3)	C24—C16—C15—C14	−1.2 (5)
C23—C22—C17—C16	−2.1 (3)	C17—C16—C15—C14	177.7 (3)
C15—C16—C17—C18	2.8 (6)	C13—C14—C15—C16	0.7 (5)
C24—C16—C17—C18	−178.1 (3)	C24—C23—C28—C29	52.8 (4)
C15—C16—C17—C22	−178.1 (3)	C22—C23—C28—C29	−60.3 (4)
C24—C16—C17—C22	1.0 (3)	C26—C23—C28—C29	176.1 (3)
C25—C24—C23—C22	177.6 (3)	C22—C17—C18—C19	0.8 (5)
C16—C24—C23—C22	−1.7 (3)	C16—C17—C18—C19	179.8 (3)
C25—C24—C23—C28	56.9 (4)	C22—C21—C20—C19	−0.3 (5)
C16—C24—C23—C28	−122.4 (3)	C22—C21—C20—Br1	−179.6 (2)
C25—C24—C23—C26	−64.9 (4)	C21—C20—C19—C18	−0.7 (5)
C16—C24—C23—C26	115.8 (3)	Br1—C20—C19—C18	178.6 (2)
C21—C22—C23—C24	−178.9 (3)	C17—C18—C19—C20	0.5 (5)
C17—C22—C23—C24	2.3 (3)	C12—C11—C10—C9	0.4 (5)
C21—C22—C23—C28	−59.1 (4)	C12—C7—C8—C9	0.4 (5)
C17—C22—C23—C28	122.1 (3)	C11—C10—C9—C8	−0.8 (5)
C21—C22—C23—C26	63.3 (4)	C7—C8—C9—C10	0.4 (6)

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6-Bromo-9,9-diethyl-N,N-diphenylfluoren-2-amine . Hydrogen-bond geometry (Å, º)

Cg5 is the centroid of the C17–C22 ring.

D—H···A	D—H	H···A	D···A	D—H···A
C2—H19···Cg5ⁱ	0.93	2.87	3.692 (4)	148

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Symmetry code: (i) −x+2, −y+1, −z+1.

References

Agilent (2012). CrysAlis PRO and CrysAlis RED. Agilent Technologies Ltd, Yarnton, England.
Bugenhagen, B., Al Jasem, Y., Al-Azani, M. & Thiemann, T. (2014). Acta Cryst. E70, o265. [DOI] [PMC free article] [PubMed]
Crundwell, G., Glagovich, N. M., Heinrich, E. M. R. & Ouellette, P. (2019). IUCrData, 4, x190553.
Dufresne, S., Skalski, T. & Skene, W. G. (2011). Can. J. Chem.89, 173–180.
Eakins, G. L., Cooper, M. W., Gerasimchuk, N. N., Phillips, T. J., Breyfogle, B. E. & Stearman, C. J. (2013). Can. J. Chem.91, 1059–1071.
Evans, P., Izod, K. & Waddell, P. G. (2016). Private communication (refcode CCDC 1488084). CCDC, Cambridge, England.
Groom, C. R., Bruno, I. J., Lightfoot, M. P. & Ward, S. C. (2016). Acta Cryst. B72, 171–179. [DOI] [PMC free article] [PubMed]
Justin Thomas, K. R., Velusamy, M., Lin, J. T., Chuen, C.-H. & Tao, Y.-T. (2005). Chem. Mater.17, 1860–1866.
Kent, G. T., Cook, A. W., Damon, P. L., Lewis, R. A., Wu, G. & Hayton, T. W. (2021). Inorg. Chem.60, 4996–5004. [DOI] [PubMed]
Melen, R. L., Eisler, D. J., Hewitt, R. A. & Rawson, J. M. (2013). Dalton Trans.42, 3888–3895. [DOI] [PubMed]
Seidel, P., Schwarzer, A. & Mazik, M. (2021). Acta Cryst. E77, 1029–1032. [DOI] [PMC free article] [PubMed]
Sheldrick, G. M. (2015a). Acta Cryst. A71, 3–8.
Sheldrick, G. M. (2015b). Acta Cryst. C71, 3–8.
Spek, A. L. (2020). Acta Cryst. E76, 1–11. [DOI] [PMC free article] [PubMed]
Sprachmann, J., Grabicki, N., Möckel, A., Maltitz, J., Monroy, J. R., Smales, G. J. & Dumele, O. (2023). Chem. Commun.59, 13639–13642. [DOI] [PubMed]
Zhang, X.-Y., Liu, B.-N., Wang, P.-B. & Liu, D.-K. (2014). Acta Cryst. E70, o1118–o1119. [DOI] [PMC free article] [PubMed]

Associated Data

This section collects any data citations, data availability statements, or supplementary materials included in this article.

Supplementary Materials

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S2414314624011763/hb4495sup1.cif

x-09-x241176-sup1.cif^{(339.8KB, cif)}

Structure factors: contains datablock(s) I. DOI: 10.1107/S2414314624011763/hb4495Isup2.hkl

x-09-x241176-Isup2.hkl^{(379.2KB, hkl)}

x-09-x241176-Isup3.cml^{(8.3KB, cml)}

Supporting information file. DOI: 10.1107/S2414314624011763/hb4495Isup3.cml

CCDC reference: 2407284

Additional supporting information: crystallographic information; 3D view; checkCIF report

[bb1] Agilent (2012). CrysAlis PRO and CrysAlis RED. Agilent Technologies Ltd, Yarnton, England.

[bb2] Bugenhagen, B., Al Jasem, Y., Al-Azani, M. & Thiemann, T. (2014). Acta Cryst. E70, o265. [DOI] [PMC free article] [PubMed]

[bb3] Crundwell, G., Glagovich, N. M., Heinrich, E. M. R. & Ouellette, P. (2019). IUCrData, 4, x190553.

[bb4] Dufresne, S., Skalski, T. & Skene, W. G. (2011). Can. J. Chem.89, 173–180.

[bb5] Eakins, G. L., Cooper, M. W., Gerasimchuk, N. N., Phillips, T. J., Breyfogle, B. E. & Stearman, C. J. (2013). Can. J. Chem.91, 1059–1071.

[bb6] Evans, P., Izod, K. & Waddell, P. G. (2016). Private communication (refcode CCDC 1488084). CCDC, Cambridge, England.

[bb7] Groom, C. R., Bruno, I. J., Lightfoot, M. P. & Ward, S. C. (2016). Acta Cryst. B72, 171–179. [DOI] [PMC free article] [PubMed]

[bb8] Justin Thomas, K. R., Velusamy, M., Lin, J. T., Chuen, C.-H. & Tao, Y.-T. (2005). Chem. Mater.17, 1860–1866.

[bb9] Kent, G. T., Cook, A. W., Damon, P. L., Lewis, R. A., Wu, G. & Hayton, T. W. (2021). Inorg. Chem.60, 4996–5004. [DOI] [PubMed]

[bb10] Melen, R. L., Eisler, D. J., Hewitt, R. A. & Rawson, J. M. (2013). Dalton Trans.42, 3888–3895. [DOI] [PubMed]

[bb11] Seidel, P., Schwarzer, A. & Mazik, M. (2021). Acta Cryst. E77, 1029–1032. [DOI] [PMC free article] [PubMed]

[bb12] Sheldrick, G. M. (2015a). Acta Cryst. A71, 3–8.

[bb13] Sheldrick, G. M. (2015b). Acta Cryst. C71, 3–8.

[bb14] Spek, A. L. (2020). Acta Cryst. E76, 1–11. [DOI] [PMC free article] [PubMed]

[bb15] Sprachmann, J., Grabicki, N., Möckel, A., Maltitz, J., Monroy, J. R., Smales, G. J. & Dumele, O. (2023). Chem. Commun.59, 13639–13642. [DOI] [PubMed]

[bb16] Zhang, X.-Y., Liu, B.-N., Wang, P.-B. & Liu, D.-K. (2014). Acta Cryst. E70, o1118–o1119. [DOI] [PMC free article] [PubMed]

PERMALINK

6-Bromo-9,9-diethyl-N,N-diphenylfluoren-2-amine

Themmila Khamrang

A Kannan

C Ponraj

Madhukar Hemamalini

G Jerald Maria Antony

Dhandayutham Saravanan

Roles

Abstract

Structure description

Figure 1.

Figure 2.

Table 1. Hydrogen-bond geometry (Å, °).

Synthesis and crystallization

Refinement

Table 2. Experimental details.

Supplementary Material

full crystallographic data

6-Bromo-9,9-diethyl-N,N-diphenylfluoren-2-amine . Crystal data

6-Bromo-9,9-diethyl-N,N-diphenylfluoren-2-amine . Data collection

6-Bromo-9,9-diethyl-N,N-diphenylfluoren-2-amine . Refinement

6-Bromo-9,9-diethyl-N,N-diphenylfluoren-2-amine . Special details

6-Bromo-9,9-diethyl-N,N-diphenylfluoren-2-amine . Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å²)

6-Bromo-9,9-diethyl-N,N-diphenylfluoren-2-amine . Atomic displacement parameters (Å²)

6-Bromo-9,9-diethyl-N,N-diphenylfluoren-2-amine . Geometric parameters (Å, º)

6-Bromo-9,9-diethyl-N,N-diphenylfluoren-2-amine . Hydrogen-bond geometry (Å, º)

References

Associated Data

Supplementary Materials

ACTIONS

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RESOURCES

Cite

Add to Collections

PERMALINK

6-Bromo-9,9-diethyl-N,N-di­phenyl­fluoren-2-amine

Themmila Khamrang

A Kannan

C Ponraj

Madhukar Hemamalini

G Jerald Maria Antony

Dhandayutham Saravanan

Roles

Abstract

Structure description

Figure 1.

Figure 2.

Table 1. Hydrogen-bond geometry (Å, °).

Synthesis and crystallization

Refinement

Table 2. Experimental details.

Supplementary Material

full crystallographic data

6-Bromo-9,9-diethyl-N,N-diphenylfluoren-2-amine . Crystal data

6-Bromo-9,9-diethyl-N,N-diphenylfluoren-2-amine . Data collection

6-Bromo-9,9-diethyl-N,N-diphenylfluoren-2-amine . Refinement

6-Bromo-9,9-diethyl-N,N-diphenylfluoren-2-amine . Special details

6-Bromo-9,9-diethyl-N,N-diphenylfluoren-2-amine . Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2)

6-Bromo-9,9-diethyl-N,N-diphenylfluoren-2-amine . Atomic displacement parameters (Å2)

6-Bromo-9,9-diethyl-N,N-diphenylfluoren-2-amine . Geometric parameters (Å, º)

6-Bromo-9,9-diethyl-N,N-diphenylfluoren-2-amine . Hydrogen-bond geometry (Å, º)

References

Associated Data

Supplementary Materials

ACTIONS

PERMALINK

RESOURCES

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6-Bromo-9,9-diethyl-N,N-diphenylfluoren-2-amine

6-Bromo-9,9-diethyl-N,N-diphenylfluoren-2-amine . Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å²)

6-Bromo-9,9-diethyl-N,N-diphenylfluoren-2-amine . Atomic displacement parameters (Å²)