Convenient one-step construction of fused or zwitterionic indanes from tetraynes.
Liu, Chencheng; Tong, Yao; Wang, Fenhua; Li, Qinghai; Organic & biomolecular chemistry 23 (2025) 4909–4916; doi:10.1039/d5ob00370a

data_7160630
_publ_section_title
;
 Convenient one-step construction of fused or zwitterionic indanes from
 tetraynes.
;
_journal_issue                   20
_journal_name_full               'Organic &amp; biomolecular chemistry'
_journal_page_first              4909
_journal_page_last               4916
_journal_paper_doi               10.1039/d5ob00370a
_journal_volume                  23
_journal_year                    2025
_chemical_formula_moiety         '2(C45 H39 N O4)'
_chemical_formula_sum            'C90 H78 N2 O8'
_chemical_formula_weight         1315.54
_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_date             2023-11-18
_audit_creation_method
;
Olex2 1.5
(compiled 2023.08.24 svn.re1ec1418 for OlexSys, GUI svn.r6817)
;
_audit_update_record
;
2025-02-26 deposited with the CCDC.	2025-04-16 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 100.575(2)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   22.9592(9)
_cell_length_b                   9.5176(4)
_cell_length_c                   33.7688(13)
_cell_measurement_reflns_used    9938
_cell_measurement_temperature    273.15
_cell_measurement_theta_max      67.70
_cell_measurement_theta_min      2.56
_cell_volume                     7253.7(5)
_computing_cell_refinement       'SAINT V8.40B (?, 2016)'
_computing_data_reduction        'SAINT V8.40B (?, 2016)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2013/2 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXS  (Sheldrick, 2008)'
_diffrn_ambient_temperature      273.15
_diffrn_measured_fraction_theta_full 0.988
_diffrn_measured_fraction_theta_max 0.986
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0781
_diffrn_reflns_av_unetI/netI     0.0625
_diffrn_reflns_Laue_measured_fraction_full 0.988
_diffrn_reflns_Laue_measured_fraction_max 0.986
_diffrn_reflns_limit_h_max       27
_diffrn_reflns_limit_h_min       -27
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       40
_diffrn_reflns_limit_l_min       -39
_diffrn_reflns_number            95633
_diffrn_reflns_point_group_measured_fraction_full 0.988
_diffrn_reflns_point_group_measured_fraction_max 0.986
_diffrn_reflns_theta_full        67.679
_diffrn_reflns_theta_max         68.415
_diffrn_reflns_theta_min         2.156
_diffrn_source_current           1.1
_diffrn_source_power             0.05500000000000001
_diffrn_source_voltage           50.0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.602
_exptl_absorpt_correction_T_max  0.7531
_exptl_absorpt_correction_T_min  0.6883
_exptl_absorpt_correction_type   none
_exptl_absorpt_process_details
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.0942 before and 0.0566 after correction.
The Ratio of minimum to maximum transmission is 0.9140.
The \l/2 correction factor is Not present.
;
_exptl_crystal_colour            'clear colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.205
_exptl_crystal_description       block
_exptl_crystal_F_000             2784
_exptl_crystal_size_max          0.5
_exptl_crystal_size_mid          0.1
_exptl_crystal_size_min          0.1
_refine_diff_density_max         0.206
_refine_diff_density_min         -0.160
_refine_diff_density_rms         0.034
_refine_ls_extinction_coef       0.00066(5)
_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   1.013
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     910
_refine_ls_number_reflns         13154
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.013
_refine_ls_R_factor_all          0.1322
_refine_ls_R_factor_gt           0.0656
_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^)+(0.0596P)^2^+1.9542P]
 where P=(Fo^2^+2Fc^2^)/3
;
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1279
_refine_ls_wR_factor_ref         0.1518
_reflns_Friedel_coverage         0.000
_reflns_number_gt                7221
_reflns_number_total             13154
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d5ob00370a2.cif
_cod_data_source_block           1_a
_cod_database_code               7160630
_shelxl_version_number           2013-2
_shelx_estimated_absorpt_t_max   0.942
_shelx_estimated_absorpt_t_min   0.753
_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:
 C2(H2), C6(H6), C19(H19), C47(H47), C50(H50), C64(H64)
2.b Secondary CH2 refined with riding coordinates:
 C10(H10A,H10B), C13(H13A,H13B), C18(H18A,H18B), C55(H55A,H55B), C57(H57A,
 H57B), C63(H63A,H63B)
2.c Aromatic/amide H refined with riding coordinates:
 C21(H21), C22(H22), C23(H23), C24(H24), C27(H27), C28(H28), C29(H29),
 C30(H30), C33(H33), C34(H34), C35(H35), C36(H36), C37(H37), C41(H41), C42(H42),
  C43(H43), C44(H44), C45(H45), C66(H66), C67(H67), C68(H68), C69(H69),
 C72(H72), C73(H73), C74(H74), C75(H75), C78(H78), C79(H79), C80(H80), C81(H81),
  C82(H82), C86(H86), C87(H87), C88(H88), C89(H89), C90(H90)
2.d Idealised Me refined as rotating group:
 C1(H1A,H1B,H1C), C3(H3A,H3B,H3C), C5(H5A,H5B,H5C), C7(H7A,H7B,H7C), C46(H46A,
 H46B,H46C), C48(H48A,H48B,H48C), C49(H49A,H49B,H49C), C51(H51A,H51B,H51C)
;
_shelx_res_checksum              82510
_olex2_submission_special_instructions 'No special instructions were received'