Enantioselective Synthesis of Triple Helicenes by Cross-Cyclotrimerization of a Helicenyl Aryne and Alkynes via Dynamic Kinetic Resolution.
Yubuta, Ayaka; Hosokawa, Tomoka; Gon, Masayuki; Tanaka, Kazuo; Chujo, Yoshiki; Tsurusaki, Akihiro; Kamikawa, Ken; Journal of the American Chemical Society 142 (2020) 10025–10033; doi:10.1021/jacs.0c01723

data_4135019
_publ_section_title
;
 Enantioselective Synthesis of Triple Helicenes by
 Cross-Cyclotrimerization of a Helicenyl Aryne and Alkynes via Dynamic
 Kinetic Resolution.
;
_journal_issue                   22
_journal_name_full               'Journal of the American Chemical Society'
_journal_page_first              10025
_journal_page_last               10033
_journal_paper_doi               10.1021/jacs.0c01723
_journal_volume                  142
_journal_year                    2020
_chemical_formula_moiety         'C50 H30 O4, C H2 Cl2'
_chemical_formula_sum            'C51 H32 Cl2 O4'
_chemical_formula_weight         779.66
_chemical_temperature_decomposition 471.15
_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'
_atom_sites_solution_hydrogens   geom
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_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   13.4699(5)
_cell_length_b                   13.6164(6)
_cell_length_c                   20.1702(9)
_cell_measurement_reflns_used    10308
_cell_measurement_temperature    103(2)
_cell_measurement_theta_max      27.4816
_cell_measurement_theta_min      3.1890
_cell_volume                     3699.4(3)
_computing_cell_refinement       'CrystalClear (Rigaku Inc., 2008)'
_computing_data_collection       'CrystalClear (Rigaku Inc., 2008)'
_computing_data_reduction        'CrystalClear (Rigaku Inc., 2008)'
_computing_molecular_graphics    '<i>ORTEP-3</i> (Farrugia, 1997)'
_computing_publication_material
'<i>SHELXL-2014/7</i> and <i>Yadokari-XG 2009</i> (Kabuto <i>et al.</i>, 2009)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_structure_solution    'SIR2014 (Giacovazzo <i>et al.</i>, 2015)'
_diffrn_ambient_temperature      103(2)
_diffrn_detector_area_resol_mean 28.5714
_diffrn_measured_fraction_theta_full 0.995
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measurement_device_type  'Saturn724+ (4x4 bin mode)'
_diffrn_measurement_method       dtprofit.ref
_diffrn_radiation_detector       CCD
_diffrn_radiation_monochromator  Confocal
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71075
_diffrn_reflns_av_R_equivalents  0.0336
_diffrn_reflns_av_unetI/netI     0.0280
_diffrn_reflns_Laue_measured_fraction_full 0.995
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_h_min       -17
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_l_max       26
_diffrn_reflns_limit_l_min       -26
_diffrn_reflns_number            38238
_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.446
_diffrn_reflns_theta_min         3.158
_diffrn_source                   'Rotating Anode'
_exptl_absorpt_coefficient_mu    0.226
_exptl_absorpt_correction_T_max  1.0000
_exptl_absorpt_correction_T_min  0.9405
_exptl_absorpt_correction_type   multi-scan
_exptl_crystal_colour            Yellow
_exptl_crystal_density_diffrn    1.400
_exptl_crystal_description       Prism
_exptl_crystal_F_000             1616
_exptl_crystal_size_max          0.170
_exptl_crystal_size_mid          0.130
_exptl_crystal_size_min          0.070
_refine_diff_density_max         0.731
_refine_diff_density_min         -1.053
_refine_diff_density_rms         0.073
_refine_ls_abs_structure_details
;
 Flack x determined using 3315 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.043(16)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.025
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     516
_refine_ls_number_reflns         8440
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.025
_refine_ls_R_factor_all          0.0581
_refine_ls_R_factor_gt           0.0561
_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^)+(0.1059P)^2^+1.9742P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1554
_refine_ls_wR_factor_ref         0.1580
_reflns_Friedel_coverage         0.803
_reflns_Friedel_fraction_full    0.998
_reflns_Friedel_fraction_max     0.999
_reflns_number_gt                8070
_reflns_number_total             8440
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            ja0c01723_si_003.cif
_cod_data_source_block           TH-1a
_cod_depositor_comments
;
The following automatic conversions were performed:

data name '_chemical_melting_point' was changed to
'_chemical_temperature_decomposition' since the value had been given
as '198 \%C, decomp.'. The value '198 \%C, decomp.' was changed to
'471.15' -- it was converted from degrees Celsius (C) to kelvins (K).

data item '_exptl_absorpt_correction_type' value 'Multi-scan' was
changed to 'multi-scan' in accordance with the
/home/data/users/saulius/crontab/automatic-downloads/rss-feeds/ACS/lib/dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.2 last updated on
2011-04-26.

Automatic conversion script
Id: cif_fix_values 7556 2019-12-06 15:28:31Z antanas 

 Adding full bibliography for 4135019.cif.

 Adding full bibliography for 4135019.cif.
;
_cod_database_code               4135019
_shelx_shelxl_version_number     2014/7
_shelx_estimated_absorpt_t_min   0.963
_shelx_estimated_absorpt_t_max   0.984
_shelx_res_checksum              84077
_shelx_hkl_checksum              72281