Preparation of phenanthrenes from ortho-amino-biphenyls and alkynes via base-promoted homolytic aromatic substitution
Marcel Hartmann; Constantin Gabriel Daniliuc; Armido Studer; Chem.Commun. 51 (2015) 3121–; doi:10.1039/C4cc10063H

data_7116504
_publ_section_title
;
 Preparation of phenanthrenes from ortho-amino-biphenyls and alkynes via
 base-promoted homolytic aromatic substitution
;
_journal_name_full               Chem.Commun.
_journal_page_first              3121
_journal_paper_doi               10.1039/C4cc10063H
_journal_volume                  51
_journal_year                    2015
_chemical_formula_sum            'C22 H18'
_chemical_formula_weight         282.36
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2ybc'
_space_group_name_H-M_alt        'P 1 21/c 1'
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 1 21/c 1'
_atom_sites_solution_hydrogens   geom
_audit_update_record
;
2014-12-16 deposited with the CCDC.
2015-01-09 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 112.4970(10)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   11.2196(4)
_cell_length_b                   12.1534(4)
_cell_length_c                   11.8670(4)
_cell_measurement_reflns_used    8872
_cell_measurement_temperature    100.(2)
_cell_measurement_theta_max      66.5874
_cell_measurement_theta_min      4.2651
_cell_volume                     1495.00(9)
_computing_cell_refinement       'SAINT V8.34A (Bruker AXS Inc., 2013)'
_computing_data_collection
;
APEX2 v.2014.1-1 (Bruker AXS Inc., 2014)
;
_computing_data_reduction        'SAINT V8.34A (Bruker AXS Inc., 2013)'
_computing_molecular_graphics    'XP (Sheldrick, 2014)'
_computing_publication_material  'SHELXL-2014 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2014 (Sheldrick, 2014)'
_computing_structure_solution    'SHELXL-2014 (Sheldrick, 2014)'
_diffrn_ambient_temperature      100.(2)
_diffrn_detector_area_resol_mean 10.4167
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device_type  'Bruker D8 Venture PHOTON 100 CMOS'
_diffrn_measurement_method       'omega and phi scans'
_diffrn_radiation_monochromator  'MX mirror'
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0307
_diffrn_reflns_av_unetI/netI     0.0229
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            15233
_diffrn_reflns_theta_full        66.60
_diffrn_reflns_theta_max         66.60
_diffrn_reflns_theta_min         4.26
_diffrn_source                   'Cu ImS'
_diffrn_source_type              'micro focus tube'
_exptl_absorpt_coefficient_mu    0.532
_exptl_absorpt_correction_T_max  0.97
_exptl_absorpt_correction_T_min  0.89
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
Bruker AXS (2014). SADABS, Version 2014/2, Bruker AXS Inc., Madison, Wisconsin,
USA.
;
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.255
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             600
_exptl_crystal_size_max          0.178
_exptl_crystal_size_mid          0.149
_exptl_crystal_size_min          0.054
_refine_diff_density_max         0.321
_refine_diff_density_min         -0.311
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.038
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     201
_refine_ls_number_reflns         2634
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.038
_refine_ls_R_factor_all          0.0445
_refine_ls_R_factor_gt           0.0383
_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^)+(0.0536P)^2^+0.6232P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0994
_refine_ls_wR_factor_ref         0.1046
_reflns_number_gt                2283
_reflns_number_total             2634
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c4cc10063h2.cif
_cod_data_source_block           stu7850
_cod_database_code               7116504
_shelx_res_checksum              38642
_shelx_hkl_checksum              25902