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_7127539
_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         'C30 H25 N O4 S, 0.5(C4 H8 O2)'
_chemical_formula_sum            'C32 H29 N O5 S'
_chemical_formula_weight         539.62
_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     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                97.243(9)
_cell_angle_beta                 100.218(5)
_cell_angle_gamma                97.968(9)
_cell_formula_units_Z            4
_cell_length_a                   8.748(3)
_cell_length_b                   14.050(5)
_cell_length_c                   22.585(8)
_cell_measurement_reflns_used    9953
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      62.13
_cell_measurement_theta_min      3.21
_cell_volume                     2673.0(16)
_computing_cell_refinement       'SAINT V8.40A (?, 2016)'
_computing_data_reduction        'SAINT V8.40A (?, 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 0.996
_diffrn_measured_fraction_theta_max 0.996
_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  0.1163
_diffrn_reflns_av_unetI/netI     0.0683
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_l_max       25
_diffrn_reflns_limit_l_min       -25
_diffrn_reflns_number            63419
_diffrn_reflns_point_group_measured_fraction_full 0.996
_diffrn_reflns_point_group_measured_fraction_max 0.996
_diffrn_reflns_theta_full        62.501
_diffrn_reflns_theta_max         62.501
_diffrn_reflns_theta_min         2.012
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    1.430
_exptl_absorpt_correction_T_max  0.7522
_exptl_absorpt_correction_T_min  0.5696
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
'SADABS-2016/2 (Bruker,2016/2) was used for absorption correction. wR2(int) was 0.1525 before and 0.0880 after correction. The Ratio of minimum to maximum transmission is 0.7572. The \l/2 correction factor is Not present.'
_exptl_crystal_colour            'clear yellowish yellow'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   yellowish
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.341
_exptl_crystal_description       needle
_exptl_crystal_F_000             1136
_exptl_crystal_size_max          0.55
_exptl_crystal_size_mid          0.45
_exptl_crystal_size_min          0.4
_refine_diff_density_max         0.586
_refine_diff_density_min         -0.377
_refine_diff_density_rms         0.094
_refine_ls_extinction_coef       0.0077(4)
_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   1.079
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     712
_refine_ls_number_reflns         8479
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.079
_refine_ls_R_factor_all          0.0768
_refine_ls_R_factor_gt           0.0680
_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^)+(0.0594P)^2^+2.9283P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1607
_refine_ls_wR_factor_ref         0.1666
_reflns_Friedel_coverage         0.000
_reflns_number_gt                7251
_reflns_number_total             8479
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d0cc06538b2.cif
_cod_data_source_block           su_5_22re1_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(C30 H25 N O4 S), C4 H8 O2'
_cod_original_formula_sum        'C64 H58 N2 O10 S2'
_cod_original_formula_units_Z    2
_cod_original_formula_weight     1079.24
_cod_database_code               7127539
_shelx_shelxl_version_number     2018/3
_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:
 C38(H45), C8(H013)
2.b Secondary CH2 refined with riding coordinates:
 C39(H44A,H44B), C9(H01A,H01B), C025(H02G,H02H)
2.c Aromatic/amide H refined with riding coordinates:
 C32(H33), C35(H36), C54(H55), C5(H00X), C49(H51), C57(H58), C50(H50),
 C55(H56), C20(H018), C14(H019), C44(H49), C47(H53), C11(H01E), C29(H01F),
 C58(H60), C2(H01H), C19(H01J), C17(H01K), C28(H01L), C13(H01M), C18(H01O),
 C48(H52), C4(H01R), C42(H47), C25(H01U), C34(H37), C43(H48), C12(H01Z),
 C26(H021), C41(H46)
2.d Idealised Me refined as rotating group:
 C52(H31A,H31B,H31C), C0aa(H01C,H01D,H01G), C59(H59A,H59B,H59C), C23(H02A,H02B,
 H02C), C30(H02D,H02E,H02F), C026(H02I,H02J,H02K)
2.e Idealised tetrahedral OH refined as rotating group:
 O6(H2), O2(H5)
;
_shelx_res_checksum              8468
_olex2_submission_special_instructions 'No special instructions were received'