Oxidative cyclization of 2-allenyl-1,1'-biphenyls with α-carbonyl alkyl bromides: facile access to functionalized phenanthrenes.
Wang, Cheng-Yong; Pan, Gao-Hui; Chen, Fan; Li, Jin-Heng; Chemical communications (Cambridge, England) 53 (2017) 4730–4733; doi:10.1039/c7cc00483d

data_7120094
_publ_section_title
;
 Oxidative cyclization of 2-allenyl-1,1'-biphenyls with \a-carbonyl alkyl
 bromides: facile access to functionalized phenanthrenes.
;
_journal_issue                   34
_journal_name_full               'Chemical communications (Cambridge, England)'
_journal_page_first              4730
_journal_page_last               4733
_journal_paper_doi               10.1039/c7cc00483d
_journal_volume                  53
_journal_year                    2017
_chemical_formula_sum            'C21 H22 O3'
_chemical_formula_weight         322.38
_space_group_crystal_system      orthorhombic
_space_group_IT_number           19
_space_group_name_Hall           'P 2ac 2ab'
_space_group_name_H-M_alt        'P 21 21 21'
_symmetry_space_group_name_Hall  'P 2ac 2ab'
_symmetry_space_group_name_H-M   'P 21 21 21'
_atom_sites_solution_hydrogens   geom
_audit_creation_method           SHELXL-2013
_audit_update_record
;
2017-03-12 deposited with the CCDC.
2017-03-31 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   5.18168(13)
_cell_length_b                   17.7177(4)
_cell_length_c                   18.7318(4)
_cell_measurement_temperature    293(2)
_cell_volume                     1719.72(7)
_computing_structure_refinement  'SHELXL-2013 (Sheldrick, 2013)'
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0775
_diffrn_reflns_av_unetI/netI     0.0364
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_k_max       21
_diffrn_reflns_limit_k_min       -21
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_number            23250
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.994
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         72.597
_diffrn_reflns_theta_min         3.434
_exptl_absorpt_coefficient_mu    0.655
_exptl_crystal_density_diffrn    1.245
_exptl_crystal_F_000             688
_refine_diff_density_max         0.263
_refine_diff_density_min         -0.207
_refine_diff_density_rms         0.044
_refine_ls_abs_structure_details
;
 Flack x determined using 1168 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons and Flack (2004), Acta Cryst. A60, s61).
;
_refine_ls_abs_structure_Flack   0.2(2)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.066
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     221
_refine_ls_number_reflns         3408
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.066
_refine_ls_R_factor_all          0.0574
_refine_ls_R_factor_gt           0.0513
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
;
 w=1/[\s^2^(Fo^2^)+(0.0940P)^2^+0.1470P]
 where P=(Fo^2^+2Fc^2^)/3
;
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1423
_refine_ls_wR_factor_ref         0.1490
_reflns_Friedel_coverage         0.695
_reflns_Friedel_fraction_full    1.000
_reflns_Friedel_fraction_max     0.988
_reflns_number_gt                3035
_reflns_number_total             3408
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c7cc00483d2.cif
_cod_data_source_block           exp_149
_cod_database_code               7120094
_shelxl_version_number           2013-2
_shelx_res_checksum              68798