Synthesis of Hexadehydrotribenzo[a,e,i][12]annulenes by Acetylene Insertion into an Open-Chain Precursor
Miroslav Dudič; Ivana Císařová; Josef Michl; Journal of Organic Chemistry 77 (2012) 68–74; doi:10.1021/jo202016v

data_4026854
_publ_section_title
;
 Synthesis of Hexadehydrotribenzo[a,e,i][12]annulenes by Acetylene
 Insertion into an Open-Chain Precursor
;
_journal_name_full               'Journal of Organic Chemistry'
_journal_page_first              68
_journal_page_last               74
_journal_paper_doi               10.1021/jo202016v
_journal_volume                  77
_journal_year                    2012
_chemical_compound_source        'synthesized by the authors'
_chemical_formula_moiety         'C36 H24 O12'
_chemical_formula_sum            'C36 H24 O12'
_chemical_formula_weight         648.55
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 1 21/c 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                 98.3440(10)
_cell_angle_gamma                90.00
_cell_formula_units_Z            16
_cell_length_a                   26.5365(6)
_cell_length_b                   32.7390(8)
_cell_length_c                   17.4054(4)
_cell_measurement_reflns_used    9914
_cell_measurement_temperature    150(2)
_cell_measurement_theta_max      26.0
_cell_measurement_theta_min      2.1
_cell_volume                     14961.4(6)
_computing_cell_refinement       'Bruker SAINT'
_computing_data_collection       'Bruker APEX2'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      150(2)
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       '\f and \w scans'
_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  0.0371
_diffrn_reflns_av_sigmaI/netI    0.0515
_diffrn_reflns_limit_h_max       32
_diffrn_reflns_limit_h_min       -20
_diffrn_reflns_limit_k_max       40
_diffrn_reflns_limit_k_min       -40
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_number            121763
_diffrn_reflns_theta_full        26.00
_diffrn_reflns_theta_max         26.00
_diffrn_reflns_theta_min         0.99
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.088
_exptl_absorpt_correction_T_max  0.9839
_exptl_absorpt_correction_T_min  0.9637
_exptl_absorpt_correction_type   multi-scan
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.152
_exptl_crystal_description       prism
_exptl_crystal_F_000             5376
_exptl_crystal_size_max          0.43
_exptl_crystal_size_mid          0.19
_exptl_crystal_size_min          0.19
_platon_squeeze_details
;
;
_refine_diff_density_max         0.449
_refine_diff_density_min         -0.225
_refine_diff_density_rms         0.056
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.885
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     1753
_refine_ls_number_reflns         29370
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.885
_refine_ls_R_factor_all          0.1079
_refine_ls_R_factor_gt           0.0543
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0946P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1470
_refine_ls_wR_factor_ref         0.1672
_reflns_number_gt                13952
_reflns_number_total             29370
_reflns_threshold_expression     I>2\s(I)
_cod_data_source_file            jo202016v_si_002.cif
_cod_data_source_block           mdu274_2
_cod_depositor_comments
;
The following automatic conversions were performed:

'_exptl_absorpt_correction_type' value 'multi-scans' was replaced
with the value 'multi-scan' as specified in the replacement file
'src/cod-tools/trunk/data/replacement-values/replacement_values.lst'.

Automatic conversion script
Id: cif_fix_values 5376 2017-05-30 11:51:03Z andrius 
;
_cod_original_sg_symbol_Hall     '-P  2ybc'
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               4026854