A macrocycle-based new organometallic nano-vessel towards sustainable C2-selective arylation of free indole in water.
Mandal, Subham; Sarkar, Piyali; Ghosh, Pradyut; Organic & biomolecular chemistry 22 (2024) 7438–7447; doi:10.1039/d4ob00886c

data_7160168
_publ_section_title
;
 A macrocycle-based new organometallic nano-vessel towards sustainable
 C2-selective arylation of free indole in water.
;
_journal_issue                   36
_journal_name_full               'Organic &amp; biomolecular chemistry'
_journal_page_first              7438
_journal_page_last               7447
_journal_paper_doi               10.1039/d4ob00886c
_journal_volume                  22
_journal_year                    2024
_chemical_formula_moiety         'C28 H35 Cl N3 O4 Pd, Cl, C2 H6 O S'
_chemical_formula_sum            'C30 H41 Cl2 N3 O5 Pd S'
_chemical_formula_weight         733.02
_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     dual
_audit_creation_date             2023-06-25
_audit_creation_method
;
Olex2 1.5
(compiled 2022.04.07 svn.rca3783a0 for OlexSys, GUI svn.r6498)
;
_audit_update_record
;
2023-06-25 deposited with the CCDC.	2024-08-19 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 109.747(10)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   8.576(3)
_cell_length_b                   38.304(13)
_cell_length_c                   10.469(4)
_cell_measurement_reflns_used    9583
_cell_measurement_temperature    140.02
_cell_measurement_theta_max      25.44
_cell_measurement_theta_min      2.32
_cell_volume                     3237(2)
_computing_cell_refinement       'SAINT V8.38A (Bruker, 2018)'
_computing_data_reduction        'SAINT V8.38A (Bruker, 2018)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL  (Sheldrick, 2008)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_diffrn_ambient_temperature      140.02
_diffrn_measured_fraction_theta_full 0.994
_diffrn_measured_fraction_theta_max 0.994
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.1073
_diffrn_reflns_av_unetI/netI     0.0932
_diffrn_reflns_Laue_measured_fraction_full 0.994
_diffrn_reflns_Laue_measured_fraction_max 0.994
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       45
_diffrn_reflns_limit_k_min       -44
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            23410
_diffrn_reflns_point_group_measured_fraction_full 0.994
_diffrn_reflns_point_group_measured_fraction_max 0.994
_diffrn_reflns_theta_full        25.026
_diffrn_reflns_theta_max         25.026
_diffrn_reflns_theta_min         2.324
_diffrn_source_current           1.0
_diffrn_source_power             0.05
_diffrn_source_voltage           50.0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.845
_exptl_absorpt_correction_T_max  0.7076
_exptl_absorpt_correction_T_min  0.4089
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.1692 before and 0.1269 after correction.
The Ratio of minimum to maximum transmission is 0.5779.
The \l/2 correction factor is Not present.
;
_exptl_crystal_colour            'clear light yellow'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.504
_exptl_crystal_description       irregular
_exptl_crystal_F_000             1512
_exptl_crystal_recrystallization_method 'Vapour deposition'
_exptl_crystal_size_max          0.6
_exptl_crystal_size_mid          0.5
_exptl_crystal_size_min          0.4
_refine_diff_density_max         1.273
_refine_diff_density_min         -1.136
_refine_diff_density_rms         0.200
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.070
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     381
_refine_ls_number_reflns         5684
_refine_ls_number_restraints     22
_refine_ls_restrained_S_all      1.068
_refine_ls_R_factor_all          0.1076
_refine_ls_R_factor_gt           0.0933
_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^)+(0.1458P)^2^+13.6780P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2378
_refine_ls_wR_factor_ref         0.2494
_reflns_Friedel_coverage         0.000
_reflns_number_gt                4705
_reflns_number_total             5684
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d4ob00886c2.cif
_cod_data_source_block           mo_pg210623_0m_a
_cod_original_cell_volume        3236.7(19)
_cod_database_code               7160168
_shelx_shelxl_version_number     2016/6
_shelx_estimated_absorpt_t_max   0.729
_shelx_estimated_absorpt_t_min   0.631
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All N(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2. Rigid bond restraints
 C8, C7, C29, S2, C30
 with sigma for 1-2 distances of 0.01 and sigma for 1-3 distances of 0.01
3. Uiso/Uaniso restraints and constraints
C29 \\sim S2 \\sim C30 \\sim C8 \\sim C7: within 2A with sigma of 0.04 and
sigma for terminal atoms of 0.08 within 2A
4.a Ternary CH refined with riding coordinates:
 N3(H3), N2(H2), N1(H1)
4.b Secondary CH2 refined with riding coordinates:
 C28(H28A,H28B), C25(H25A,H25B), C27(H27A,H27B), C23(H23A,H23B), C26(H26A,
 H26B), C10(H10A,H10B), C24(H24A,H24B), C9(H9A,H9B), C8(H8A,H8B), C7(H7A,H7B)
4.c Aromatic/amide H refined with riding coordinates:
 C19(H19), C5(H5), C15(H15), C18(H18), C16(H16), C4(H4), C22(H22), C21(H21),
 C2(H2A), C12(H12), C3(H3A), C13(H13)
4.d Idealised Me refined as rotating group:
 C30(H30A,H30B,H30C), C29(H29A,H29B,H29C)
;
_shelx_res_checksum              65660
_olex2_submission_special_instructions 'No special instructions were received'