Synthesis of sterically congested double helicene by alkyne cycloisomerization.
Hirano, Junichiro; Miyoshi, Sayaka; Yashima, Eiji; Ikai, Tomoyuki; Shinokubo, Hiroshi; Fukui, Norihito; Chemical communications (Cambridge, England) 60 (2024) 6035–6038; doi:10.1039/d4cc01573h

data_7133070
_publ_section_title
;
 Synthesis of sterically congested double helicene by alkyne
 cycloisomerization.
;
_journal_issue                   47
_journal_name_full               'Chemical communications (Cambridge, England)'
_journal_page_first              6035
_journal_page_last               6038
_journal_paper_doi               10.1039/d4cc01573h
_journal_volume                  60
_journal_year                    2024
_chemical_formula_moiety         'C H Cl3, C106 H96 O4'
_chemical_formula_sum            'C107 H97 Cl3 O4'
_chemical_formula_weight         1553.19
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2024-03-14
_audit_creation_method
;
Olex2 1.5
(compiled 2023.08.24 svn.re1ec1418 for OlexSys, GUI svn.r6817)
;
_audit_update_record
;
2024-04-05 deposited with the CCDC.	2024-05-17 downloaded from the CCDC.
;
_cell_angle_alpha                92.731(2)
_cell_angle_beta                 92.591(2)
_cell_angle_gamma                108.886(2)
_cell_formula_units_Z            2
_cell_length_a                   10.8817(3)
_cell_length_b                   15.6992(4)
_cell_length_c                   25.2074(6)
_cell_measurement_reflns_used    8739
_cell_measurement_temperature    93
_cell_measurement_theta_max      30.2970
_cell_measurement_theta_min      2.1500
_cell_volume                     4061.44(19)
_computing_cell_refinement       'CrysAlisPro 1.171.42.49 (Rigaku OD, 2022)'
_computing_data_collection       'CrysAlisPro 1.171.42.49 (Rigaku OD, 2022)'
_computing_data_reduction        'CrysAlisPro 1.171.42.49 (Rigaku OD, 2022)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_diffrn_ambient_temperature      93
_diffrn_detector                 'CCD plate'
_diffrn_detector_type            'Rigaku Saturn-N'
_diffrn_measured_fraction_theta_full 0.973
_diffrn_measured_fraction_theta_max 0.834
_diffrn_measurement_details
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  t~exp~   \w     \q     \k     \f   Frames
  1  \w   -110.00  70.00   0.50   10.00    --  -20.00  45.00   0.00  360
  2  \w   -110.00  70.00   0.50   10.00    --  -20.00  45.00  90.00  360
;
_diffrn_measurement_device       'abstract diffractometer'
_diffrn_measurement_device_type
'dtrek-CrysAlisPro-abstract goniometer imported rigaku-d*trek images'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0544611000
_diffrn_orient_matrix_UB_12      0.0013762000
_diffrn_orient_matrix_UB_13      -0.0160659000
_diffrn_orient_matrix_UB_21      -0.0075633000
_diffrn_orient_matrix_UB_22      -0.0435704000
_diffrn_orient_matrix_UB_23      -0.0116489000
_diffrn_orient_matrix_UB_31      -0.0417431000
_diffrn_orient_matrix_UB_32      -0.0197456000
_diffrn_orient_matrix_UB_33      0.0200762000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0622
_diffrn_reflns_av_unetI/netI     0.1389
_diffrn_reflns_Laue_measured_fraction_full 0.973
_diffrn_reflns_Laue_measured_fraction_max 0.834
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_k_max       20
_diffrn_reflns_limit_k_min       -22
_diffrn_reflns_limit_l_max       25
_diffrn_reflns_limit_l_min       -35
_diffrn_reflns_number            37650
_diffrn_reflns_point_group_measured_fraction_full 0.973
_diffrn_reflns_point_group_measured_fraction_max 0.834
_diffrn_reflns_theta_full        26.000
_diffrn_reflns_theta_max         30.931
_diffrn_reflns_theta_min         2.093
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_source_target            Mo
_diffrn_source_type              'Enhance (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    0.170
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.63851
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.42.49 (Rigaku Oxford Diffraction, 2022)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            yellow
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.270
_exptl_crystal_description       block
_exptl_crystal_F_000             1644
_exptl_crystal_size_max          0.469
_exptl_crystal_size_mid          0.406
_exptl_crystal_size_min          0.157
_refine_diff_density_max         0.702
_refine_diff_density_min         -0.531
_refine_diff_density_rms         0.074
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.005
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     1039
_refine_ls_number_reflns         21468
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.005
_refine_ls_R_factor_all          0.1577
_refine_ls_R_factor_gt           0.0739
_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^)+(0.0744P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1584
_refine_ls_wR_factor_ref         0.2077
_reflns_Friedel_coverage         0.000
_reflns_number_gt                10884
_reflns_number_total             21468
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d4cc01573h2.cif
_cod_data_source_block           20240312_hj_autored
_cod_depositor_comments          'Adding full bibliography for 7133070.cif.'
_cod_database_code               7133070
_shelx_shelxl_version_number     2018/3
_shelx_estimated_absorpt_t_max   0.974
_shelx_estimated_absorpt_t_min   0.924
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Ternary CH refined with riding coordinates:
 C107(H107)
2.b Secondary CH2 refined with riding coordinates:
 C101(H10A,H10B), C102(H10C,H10D), C103(H10E,H10F), C49(H49A,H49B), C50(H50A,
 H50B), C23(H23A,H23B), C76(H76A,H76B), C75(H75A,H75B), C51(H51A,H51B),
 C77(H77A,H77B), C24(H24A,H24B), C25(H25A,H25B)
2.c Aromatic/amide H refined with riding coordinates:
 C57(H57), C97(H97), C65(H65), C95(H95), C91(H91), C86(H86), C63(H63),
 C56(H56), C61(H61), C19(H19), C5(H5), C43(H43), C82(H82), C31(H31), C87(H87),
 C69(H69), C30(H30), C89(H89), C17(H17), C83(H83), C13(H13), C62(H62), C45(H45),
  C39(H39), C4(H4), C60(H60), C88(H88), C11(H11), C71(H71), C8(H8), C34(H34),
 C37(H37), C9(H9), C10(H10), C35(H35), C36(H36)
2.d Idealised Me refined as rotating group:
 C99(H99A,H99B,H99C), C22(H22A,H22B,H22C), C73(H73A,H73B,H73C), C47(H47A,H47B,
 H47C), C100(H10G,H10H,H10I), C48(H48A,H48B,H48C), C21(H21A,H21B,H21C),
 C104(H10J,H10K,H10L), C74(H74A,H74B,H74C), C52(H52A,H52B,H52C), C78(H78A,H78B,
 H78C), C26(H26A,H26B,H26C)
;
_shelx_res_checksum              59934
_shelx_hkl_checksum              32232
_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
- Detector area scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 2.949
_oxdiff_exptl_absorpt_empirical_full_min 0.432