To Flip or Not To Flip? Assessing the Inversion Barrier of the Tetraphenylene Framework with Enantiopure 2,15-Dideuteriotetraphenylene and 2,7-Dimethyltetraphenylene
Hui Huang; Timothy Stewart; Matthias Gutmann; Takashi Ohhara; Nobuo Niimura; Yu-Xue Li; Jian-Feng Wen; Robert Bau; Henry N. C. Wong; Journal of Organic Chemistry 74 (2009) 359–369; doi:10.1021/jo802061p

data_4024238
_publ_contact_author
;
      Dr. Henry N.C. Wong
      Shanghai-Hong Kong Joint Laboratory in Chemical Synthesis
      The Chinese Academy of Sciences
      354 Feng Lin Road
      Shanghai 200032
      China
;
_publ_contact_author_email       hncwong@cuhk.edu.hk
_publ_section_title
;
To Flip or Not To Flip? Assessing the Inversion Barrier of the
Tetraphenylene Framework with Enantiopure 2,15-Dideuteriotetraphenylene and
2,7-Dimethyltetraphenylene
;
_journal_name_full               'Journal of Organic Chemistry'
_journal_page_first              359
_journal_page_last               369
_journal_paper_doi               10.1021/jo802061p
_journal_volume                  74
_journal_year                    2009
_chemical_formula_moiety         'C24 H12 D4'
_chemical_formula_sum            'C24 H12 D4'
_chemical_formula_weight         308.4148
_chemical_name_common            tetraphenylene
_chemical_name_systematic        Dideuteriotetraphenylene
_space_group_IT_number           5
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  'C 2y'
_symmetry_space_group_name_H-M   'C 1 2 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 100.976(2)
_cell_angle_gamma                90.00
_cell_formula_units_Z            8
_cell_length_a                   15.423(2)
_cell_length_b                   13.0638(18)
_cell_length_c                   16.267(2)
_cell_measurement_reflns_used    9161
_cell_measurement_temperature    30(2)
_cell_measurement_theta_max      +165
_cell_measurement_theta_min      +12.5
_cell_volume                     3217.6(8)
_computing_data_collection       'ISIS inst_ctrl_prgm_(Akeroyed et al. 2002)'
_computing_data_reduction        SXD2001
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      30(2)
_diffrn_measured_fraction_theta_full 0.241
_diffrn_measured_fraction_theta_max 0.242
_diffrn_measurement_device_type  SXD
_diffrn_measurement_method       'time-of-flight LAUE diffraction'
_diffrn_radiation_monochromator  none
_diffrn_radiation_probe          neutron
_diffrn_radiation_source         'synchroton spallation source'
_diffrn_radiation_type           'polychromatic beam of neutrons'
_diffrn_radiation_wavelength     0
_diffrn_reflns_av_R_equivalents  0.0000
_diffrn_reflns_av_sigmaI/netI    0.0792
_diffrn_reflns_limit_h_max       44
_diffrn_reflns_limit_h_min       -45
_diffrn_reflns_limit_k_max       36
_diffrn_reflns_limit_k_min       -39
_diffrn_reflns_limit_l_max       37
_diffrn_reflns_limit_l_min       -48
_diffrn_reflns_number            32220
_diffrn_reflns_theta_full        84.66
_diffrn_reflns_theta_max         84.66
_diffrn_reflns_theta_min         7.83
_diffrn_standards_decay_%        0
_diffrn_standards_interval_count 0
_diffrn_standards_interval_time  0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.000
_exptl_absorpt_correction_T_max  2.2617
_exptl_absorpt_correction_T_min  1.6175
_exptl_absorpt_correction_type   sphere
_exptl_absorpt_process_details   'Gaussian intergration with 32 grid points'
_exptl_crystal_colour            'pale yellow'
_exptl_crystal_density_diffrn    1.263
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       rod
_exptl_crystal_F_000             964
_exptl_crystal_size_max          3.0
_exptl_crystal_size_mid          2.5
_exptl_crystal_size_min          1.5
_refine_diff_density_max         7.800
_refine_diff_density_min         -3.590
_refine_diff_density_rms         0.721
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0(0)
_refine_ls_extinction_coef       0.00285(4)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_ref   1.023
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     312
_refine_ls_number_reflns         32220
_refine_ls_number_restraints     25
_refine_ls_restrained_S_all      1.023
_refine_ls_R_factor_all          0.0790
_refine_ls_R_factor_gt           0.0790
_refine_ls_shift/su_max          0.023
_refine_ls_shift/su_mean         0.003
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0982P)^2^+393.7392P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1991
_refine_ls_wR_factor_ref         0.1991
_reflns_number_gt                32220
_reflns_number_total             32220
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jo802061p_si_005.cif
_cod_data_source_block           tbcot
_cod_depositor_comments
;
 Changing _atom_site_type_symbol data item values that represent deuterium
 from 'Dh' to 'D'.

 Antanas Vaitkus,
 2017-01-20
;
_cod_original_sg_symbol_H-M      C2
_cod_database_code               4024238