Palladium(ii) catalysed cascade strategy for the synthesis of dibenzo[5,6:7,8]cycloocta[1,2-b]indol-10-ols/-10(15H)-ones: easy access to 1,3,5,7-cyclooctatetraenes (COTs).
De, Sukanya; Jash, Moumita; Chowdhury, Chinmay; Chemical communications (Cambridge, England) 56 (2020) 15659–15662; doi:10.1039/d0cc06538b

data_7127535
_publ_section_title
;
 Palladium(ii) catalysed cascade strategy for the synthesis of
 dibenzo[5,6:7,8]cycloocta[1,2-b]indol-10-ols/-10(15H)-ones: easy access
 to 1,3,5,7-cyclooctatetraenes (COTs).
;
_journal_issue                   100
_journal_name_full               'Chemical communications (Cambridge, England)'
_journal_page_first              15659
_journal_page_last               15662
_journal_paper_doi               10.1039/d0cc06538b
_journal_volume                  56
_journal_year                    2020
_chemical_formula_moiety         'C29 H23 N O3 S, 0.5(C H2 Cl2)'
_chemical_formula_sum            'C29.5 H24 Cl N O3 S'
_chemical_formula_weight         508.00
_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     iterative
_audit_creation_date             2020-08-19
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_audit_update_record
;
2020-09-28 deposited with the CCDC.	2020-11-11 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 92.018(2)
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   8.3459(3)
_cell_length_b                   31.8448(10)
_cell_length_c                   18.0413(6)
_cell_measurement_reflns_used    8844
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      66.158
_cell_measurement_theta_min      2.775
_cell_volume                     4791.9(3)
_computing_cell_refinement       'SAINT V8.38A (?, 2016)'
_computing_data_reduction        'SAINT V8.38A (?, 2016)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'olex2.solve (Bourhis et al., 2015)'
_diffrn_ambient_temperature      100.0
_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_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.1452
_diffrn_reflns_av_unetI/netI     0.0768
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       37
_diffrn_reflns_limit_k_min       -37
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_number            88704
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_theta_full        66.672
_diffrn_reflns_theta_max         66.672
_diffrn_reflns_theta_min         2.775
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    2.498
_exptl_absorpt_correction_T_max  0.7528
_exptl_absorpt_correction_T_min  0.5554
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
'SADABS-2016/2 (Bruker,2016/2) was used for absorption correction. wR2(int) was 0.1488 before and 0.0996 after correction. The Ratio of minimum to maximum transmission is 0.7378. The \l/2 correction factor is Not present.'
_exptl_crystal_colour            'dull yellowish yellow'
_exptl_crystal_colour_lustre     dull
_exptl_crystal_colour_modifier   yellowish
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.408
_exptl_crystal_description       needle
_exptl_crystal_F_000             2120
_exptl_crystal_size_max          0.18
_exptl_crystal_size_mid          0.04
_exptl_crystal_size_min          0.02
_refine_diff_density_max         0.469
_refine_diff_density_min         -0.452
_refine_diff_density_rms         0.113
_refine_ls_extinction_coef       0.0052(3)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2018/3 (Sheldrick 2018)'
_refine_ls_goodness_of_fit_ref   1.222
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     645
_refine_ls_number_reflns         8465
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.222
_refine_ls_R_factor_all          0.0949
_refine_ls_R_factor_gt           0.0876
_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^)+(0.0548P)^2^+11.3236P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1861
_refine_ls_wR_factor_ref         0.1904
_reflns_Friedel_coverage         0.000
_reflns_number_gt                7840
_reflns_number_total             8465
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d0cc06538b2.cif
_cod_data_source_block           su_3_185_au_0m_a
_cod_depositor_comments
;
Adding full bibliography for 7127535--7127539.cif.

2024-12-16
Z value and formula fixed to values more according to usual
chemical conventions.                 miguel
;
_cod_original_formula_moiety     '2(C29 H23 N O3 S), C H2 Cl2'
_cod_original_formula_sum        'C59 H48 Cl2 N2 O6 S2'
_cod_original_formula_units_Z    4
_cod_original_formula_weight     1016.01
_cod_database_code               7127535
_shelx_shelxl_version_number     2018/3
_shelx_estimated_absorpt_t_max   0.952
_shelx_estimated_absorpt_t_min   0.662
_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, All O(H) groups
2.a Ternary CH refined with riding coordinates:
 C15(H15), C38(H38)
2.b Secondary CH2 refined with riding coordinates:
 C29(H29A,H29B), C39(H39A,H39B), C01Z(H01A,H01B)
2.c Aromatic/amide H refined with riding coordinates:
 C32(H32), C35(H35), C25(H25), C47(H47), C7(H7), C52(H52), C19(H19), C18(H18),
 C11(H11), C3(H3), C56(H56), C21(H21), C6(H6), C26(H26), C44(H44), C57(H57),
 C31(H31), C28(H28), C20(H20), C41(H41), C30(H30), C53(H53), C48(H48), C8(H8),
 C4(H4A), C10(H10), C27(H27), C43(H43), C50(H50), C42(H42), C9(H9), C49(H49)
2.d Idealised Me refined as rotating group:
 C1(H1A,H1B,H1C), C55(H55A,H55B,H55C)
2.e Idealised tetrahedral OH refined as rotating group:
 O4(H4), O1(H1)
;
_shelx_res_checksum              17748
_olex2_submission_special_instructions 'No special instructions were received'