Synthesis of 1,3-Diphenyl-6-alkyl/aryl-Substituted Fulvene Chromophores: Observation of π-π Interactions in a 6-Pyrene-Substituted 1,3-Diphenylfulvene
Andrew J. Peloquin; Rebecca L. Stone; Sarah E. Avila; Erlyn R. Rudico; Christopher B. Horn; Kim A. Gardner; David W. Ball; Jane E. B. Johnson; Scott T. Iacono; Gary J. Balaich; Journal of Organic Chemistry 77 (2012) 6371–6376; doi:10.1021/jo301101x

data_4027336
_publ_section_title
;
 Synthesis of 1,3-Diphenyl-6-alkyl/aryl-Substituted Fulvene Chromophores:
 Observation of \p-\p Interactions in a 6-Pyrene-Substituted
 1,3-Diphenylfulvene
;
_journal_name_full               'Journal of Organic Chemistry'
_journal_page_first              6371
_journal_page_last               6376
_journal_paper_doi               10.1021/jo301101x
_journal_volume                  77
_journal_year                    2012
_chemical_formula_iupac          'C24 H18'
_chemical_formula_moiety         'C24 H18'
_chemical_formula_sum            'C24 H18'
_chemical_formula_weight         306.38
_chemical_name_common            1,3,6-triphenylfulvene
_chemical_name_systematic        1,3,6-triphenylfulvene
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 1 21/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           'APEX2 v2009.7-0'
_cell_angle_alpha                90
_cell_angle_beta                 99.761(4)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   17.449(6)
_cell_length_b                   5.698(2)
_cell_length_c                   16.787(6)
_cell_measurement_reflns_used    6255
_cell_measurement_temperature    100.(2)
_cell_measurement_theta_max      29.3518
_cell_measurement_theta_min      2.3688
_cell_volume                     1644.9(10)
_computing_cell_refinement       'SAINT V7.66A (Bruker AXS, 2009)'
_computing_data_collection       'Bruker SMART APEX'
_computing_data_reduction        'SAINT V7.66A (Bruker AXS, 2009)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      100.(2)
_diffrn_detector_area_resol_mean 8.3660
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_device_type  'Bruker SMART APEX CCD'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0289
_diffrn_reflns_av_sigmaI/netI    0.0253
_diffrn_reflns_limit_h_max       22
_diffrn_reflns_limit_h_min       -22
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_number            15993
_diffrn_reflns_theta_full        27.48
_diffrn_reflns_theta_max         27.48
_diffrn_reflns_theta_min         2.37
_exptl_absorpt_coefficient_mu    0.070
_exptl_absorpt_correction_T_max  0.99
_exptl_absorpt_correction_T_min  0.89
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'Bruker SADABS, Version 2008/1'
_exptl_crystal_colour            red
_exptl_crystal_density_diffrn    1.237
_exptl_crystal_description       'rectangular prism'
_exptl_crystal_F_000             648
_exptl_crystal_size_max          0.36
_exptl_crystal_size_mid          0.29
_exptl_crystal_size_min          0.12
_refine_diff_density_max         0.334
_refine_diff_density_min         -0.162
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.032
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     217
_refine_ls_number_reflns         3772
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.032
_refine_ls_R_factor_all          0.0465
_refine_ls_R_factor_gt           0.0414
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0524P)^2^+0.5700P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1047
_refine_ls_wR_factor_ref         0.1085
_reflns_number_gt                3342
_reflns_number_total             3772
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jo301101x_si_003_2.cif
_cod_data_source_block           compound_6
_cod_database_code               4027336