Kinetic Control in the Synthesis of a Möbius Tris((ethynyl)[5]helicene) Macrocycle Using Alkyne Metathesis.
Moore, Jeffrey S.; Jiang, Xing; Laffoon, Summer D.; Chen, Dandan; Pérez-Estrada, Salvador; Danis, Andrew S.; Rodríguez-López, Joaquín; Garcia-Garibay, Miguel A; Zhu, Jun; Journal of the American Chemical Society  (2020) –; doi:10.1021/jacs.0c01430

data_4134585
_publ_section_title
;
 Kinetic Control in the Synthesis of a M\"obius Tris((ethynyl)[5]helicene)
 Macrocycle Using Alkyne Metathesis.
;
_journal_name_full               'Journal of the American Chemical Society'
_journal_paper_doi               10.1021/jacs.0c01430
_journal_year                    2020
_chemical_formula_moiety         'C72 H36, 2(C4 H8 O2)'
_chemical_formula_sum            'C80 H52 O4'
_chemical_formula_weight         1077.21
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2yn'
_space_group_name_H-M_alt        'P 1 21/n 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_audit_creation_method           SHELXL-2018/3
_audit_update_record
; 
? 
;
_cell_angle_alpha                90
_cell_angle_beta                 101.2770(5)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   16.2790(3)
_cell_length_b                   17.6696(3)
_cell_length_c                   19.8265(3)
_cell_measurement_reflns_used    38052
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      26.38
_cell_measurement_theta_min      2.31
_cell_volume                     5592.86(16)
_computing_cell_refinement       'SAINT V8.38A (Bruker, 2014)'
_computing_data_collection       'APEX3 V2018.7-2 (Bruker, 2018)'
_computing_data_reduction
; 
SAINT V8.38A, XPREP v2014/2, (Bruker, 2014), SADABS V2016/2 
(Krause et al., 2015) 
;
_computing_molecular_graphics
; 
SHELXTL v2014-7 (Bruker, 2014), CrystalMaker v9.2.8 (CrystalMaker, 2016) 
;
_computing_publication_material  'XCIF V2014-2 (Bruker, 2014)'
_computing_structure_refinement  'SHELXL-2018-3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXS-2013-1 (Sheldrick, 2015)'
_diffrn_ambient_temperature      100(2)
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device       'Bruker D8 Venture/Photon II'
_diffrn_measurement_method       'profile data from \f and \w scans'
_diffrn_radiation_monochromator  'multilayer mirrors'
_diffrn_radiation_source         'microfocus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_wavelength_id  dd41xs
_diffrn_reflns_av_R_equivalents  0.0387
_diffrn_reflns_av_unetI/netI     0.0201
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       20
_diffrn_reflns_limit_h_min       -20
_diffrn_reflns_limit_k_max       22
_diffrn_reflns_limit_k_min       -22
_diffrn_reflns_limit_l_max       24
_diffrn_reflns_limit_l_min       -24
_diffrn_reflns_number            107332
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.381
_diffrn_reflns_theta_min         2.305
_exptl_absorpt_coefficient_mu    0.077
_exptl_absorpt_correction_T_max  0.7454
_exptl_absorpt_correction_T_min  0.7103
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS V2016/2 (Krause et al., 2015)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.279
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             2256
_exptl_crystal_id                dd41xs
_exptl_crystal_preparation
; 
The data crystal was mounted using oil (Paratone-N, Exxon) to a 
0.3 mm cryo-loop (Hampton Research) with the (5 -1 -6) scattering 
planes roughly normal to the spindle axis. 
;
_exptl_crystal_size_max          0.434
_exptl_crystal_size_mid          0.257
_exptl_crystal_size_min          0.150
_refine_diff_density_max         0.723
_refine_diff_density_min         -0.322
_refine_diff_density_rms         0.048
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.029
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     818
_refine_ls_number_reflns         11441
_refine_ls_number_restraints     180
_refine_ls_restrained_S_all      1.050
_refine_ls_R_factor_all          0.0554
_refine_ls_R_factor_gt           0.0487
_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^)+(0.0522P)^2^+3.8691P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1211
_refine_ls_wR_factor_ref         0.1269
_reflns_Friedel_coverage         0.000
_reflns_number_gt                9980
_reflns_number_total             11441
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            ja0c01430_si_002.cif
_cod_data_source_block           dd41xs
_cod_original_sg_symbol_H-M      'P 21/n'
_cod_database_code               4134585
_shelx_shelxl_version_number     2018/3
_shelx_estimated_absorpt_t_min   0.967
_shelx_estimated_absorpt_t_max   0.988
_shelx_res_checksum              13868
_shelx_hkl_checksum              21939