Synthesis of Sterically Hindered 4,5-Diarylphenanthrenes via Acid-catalyzed Bisannulation of Benzenediacetaldehydes with Alkynes
Li, Yuanming; Yagi, Akiko; Itami, Kenichiro; Chemical Science  (2019) –; doi:10.1039/C9SC00334G

data_1550901
_publ_section_title
;
 Synthesis of Sterically Hindered 4,5-Diarylphenanthrenes via
 Acid-catalyzed Bisannulation of Benzenediacetaldehydes with Alkynes
;
_journal_name_full               'Chemical Science'
_journal_paper_doi               10.1039/C9SC00334G
_journal_year                    2019
_chemical_absolute_configuration unk
_chemical_formula_sum            'C34 H34'
_chemical_formula_weight         442.61
_space_group_crystal_system      monoclinic
_space_group_IT_number           15
_space_group_name_Hall           '-C 2yc'
_space_group_name_H-M_alt        'C 1 2/c 1'
_symmetry_space_group_name_Hall  '-C 2yc'
_symmetry_space_group_name_H-M   'C 1 2/c 1'
_atom_sites_solution_hydrogens   geom
_audit_creation_method           SHELXL-2016/6
_audit_update_record
;
2018-09-04 deposited with the CCDC.    2019-04-17 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 94.442(4)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   14.0303(19)
_cell_length_b                   23.979(4)
_cell_length_c                   7.3735(11)
_cell_measurement_reflns_used    2814
_cell_measurement_temperature    123
_cell_measurement_theta_max      25.4
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_cell_volume                     2473.2(6)
_computing_cell_refinement
;
Rigaku CrystalClear-SM Expert 2.1 b29
;
_computing_data_collection
;
Rigaku CrystalClear-SM Expert 2.1 b29
;
_computing_data_reduction
;
Rigaku CrystalClear-SM Expert 2.1 b29
;
_computing_molecular_graphics    'Yadokari-XG 2009 (Wakita Nemoto et al., 2009)'
_computing_publication_material  'Yadokari-XG 2009 (Wakita,Nemoto et al., 2009)'
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_computing_structure_solution    SIR-97
_diffrn_ambient_temperature      123(2)
_diffrn_detector_area_resol_mean 5.8140
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_device_type
;
Rigaku CrystalClear-SM Expert 2.1 b29
;
_diffrn_measurement_method       'profile data from \w-scans'
_diffrn_radiation_monochromator  Confocal
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71075
_diffrn_reflns_av_R_equivalents  0.0268
_diffrn_reflns_av_unetI/netI     0.0153
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_k_max       28
_diffrn_reflns_limit_k_min       -28
_diffrn_reflns_limit_l_max       8
_diffrn_reflns_limit_l_min       -8
_diffrn_reflns_number            13626
_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_theta_full        24.999
_diffrn_reflns_theta_max         24.999
_diffrn_reflns_theta_min         3.146
_diffrn_source                   'Rotating Anode'
_exptl_absorpt_coefficient_mu    0.067
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.839
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'Jacobson, R. (1998) Private communication'
_exptl_crystal_colour            Colorless
_exptl_crystal_density_diffrn    1.189
_exptl_crystal_description       Block
_exptl_crystal_F_000             952
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_exptl_crystal_size_min          0.10
_refine_diff_density_max         0.172
_refine_diff_density_min         -0.178
_refine_diff_density_rms         0.033
_refine_ls_extinction_method     none
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_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
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_refine_ls_number_reflns         2188
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.027
_refine_ls_R_factor_all          0.0413
_refine_ls_R_factor_gt           0.0337
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0488P)^2^+1.2487P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0872
_refine_ls_wR_factor_ref         0.0913
_reflns_Friedel_coverage         0.000
_reflns_number_gt                1869
_reflns_number_total             2188
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c9sc00334g2.cif
_cod_data_source_block           3c
_cod_database_code               1550901
_shelx_shelxl_version_number     2016/6
_shelx_estimated_absorpt_t_min   0.990
_shelx_estimated_absorpt_t_max   0.993
_shelx_res_checksum              24519