Syntheses and reactivity of naphthalenyl-substituted arenediynes.
Korovina, Nadezhda V.; Chang, Michael L.; Nguyen, Trang T.; Fernandez, Ramiro; Walker, Heather J.; Olmstead, Marilyn M.; Gherman, Benjamin F.; Spence, John D.; Organic letters 13 (2011) 3660–3663; doi:10.1021/ol201317w

data_1502281
_publ_section_title
;
 Syntheses and reactivity of naphthalenyl-substituted arenediynes.
;
_journal_issue                   14
_journal_name_full               'Organic letters'
_journal_page_first              3660
_journal_page_last               3663
_journal_paper_doi               10.1021/ol201317w
_journal_volume                  13
_journal_year                    2011
_chemical_formula_moiety         'C60 H36, C H2 Cl2'
_chemical_formula_sum            'C61 H38 Cl2'
_chemical_formula_weight         841.81
_chemical_name_common            'Compound 5a'
_chemical_name_systematic
; 
 ? 
;
_space_group_IT_number           2
_symmetry_cell_setting           triclinic
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                115.647(2)
_cell_angle_beta                 107.906(2)
_cell_angle_gamma                91.763(2)
_cell_formula_units_Z            2
_cell_length_a                   10.0288(4)
_cell_length_b                   15.9042(6)
_cell_length_c                   15.9492(6)
_cell_measurement_reflns_used    9921
_cell_measurement_temperature    90(2)
_cell_measurement_theta_max      31.5
_cell_measurement_theta_min      2.75
_cell_volume                     2142.01(15)
_computing_cell_refinement       'SAINT (Bruker, 2007)'
_computing_data_collection       'Apex2 (Bruker, 2007)'
_computing_data_reduction        'SAINT (Bruker, 2007)'
_computing_molecular_graphics    'SHELXTL 5.1, XP (Sheldrick, 1994)'
_computing_publication_material  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      90(2)
_diffrn_detector_area_resol_mean 8.3
_diffrn_measured_fraction_theta_full 0.995
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measurement_device_type  'Bruker SMART ApexII'
_diffrn_measurement_method       \w
_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  0.0198
_diffrn_reflns_av_sigmaI/netI    0.0248
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       22
_diffrn_reflns_limit_k_min       -22
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_number            31783
_diffrn_reflns_theta_full        29.57
_diffrn_reflns_theta_max         29.57
_diffrn_reflns_theta_min         2.68
_exptl_absorpt_coefficient_mu    0.194
_exptl_absorpt_correction_T_max  0.983
_exptl_absorpt_correction_T_min  0.876
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS (Sheldrick, 1996)'
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.305
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       needle
_exptl_crystal_F_000             876
_exptl_crystal_size_max          0.70
_exptl_crystal_size_mid          0.19
_exptl_crystal_size_min          0.09
_refine_diff_density_max         0.615
_refine_diff_density_min         -0.686
_refine_diff_density_rms         0.055
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.003
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     575
_refine_ls_number_reflns         11942
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.003
_refine_ls_R_factor_all          0.0585
_refine_ls_R_factor_gt           0.0462
_refine_ls_shift/su_max          0.006
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0670P)^2^+1.0536P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1197
_refine_ls_wR_factor_ref         0.1284
_reflns_number_gt                9671
_reflns_number_total             11942
_reflns_threshold_expression     I>2\s(I)
_cod_data_source_file            ol201317w_si_003.cif
_cod_data_source_block           mn1898
_cod_original_cell_volume        2142.01(14)
_cod_database_code               1502281