A combined experimental and theoretical rationalization of an unusual zinc(ii)-mediated conversion of 18-membered Schiff-base macrocycles to 18-membered imine‒amine macrocycles with imidazolidine side rings: an investigation of their bio-relevant catalytic activities
Chakraborty, Tonmoy; Mukherjee, Somali; Parveen, Rumana; Chandra, Arpita; Samanta, Debabrata; Das, Debasis; New Journal of Chemistry 45 (2021) 2550–2562; doi:10.1039/D0NJ05635A

data_7060265
_publ_section_title
;
 A combined experimental and theoretical rationalization of an unusual
 zinc(ii)-mediated conversion of 18-membered Schiff-base macrocycles to
 18-membered imine--amine macrocycles with imidazolidine side rings: an
 investigation of their bio-relevant catalytic activities
;
_journal_issue                   5
_journal_name_full               'New Journal of Chemistry'
_journal_page_first              2550
_journal_page_last               2562
_journal_paper_doi               10.1039/D0NJ05635A
_journal_volume                  45
_journal_year                    2021
_chemical_formula_moiety         'C30 H41 Br4.89 N6 O2 Zn2.95, C H4 O, H2 O'
_chemical_formula_sum            'C31 H47 Br4.89 N6 O4 Zn2.95'
_chemical_formula_weight         1151.03
_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   mixed
_audit_creation_date             2020-02-02
_audit_creation_method
;
Olex2 1.2
(compiled 2016.02.19 svn.r3266 for OlexSys, GUI svn.r5155)
;
_audit_update_record
;
2020-03-26 deposited with the CCDC.	2021-01-04 downloaded from the CCDC.
;
_cell_angle_alpha                63.783(9)
_cell_angle_beta                 81.070(9)
_cell_angle_gamma                84.834(9)
_cell_formula_units_Z            2
_cell_length_a                   10.728(6)
_cell_length_b                   14.280(7)
_cell_length_c                   14.804(7)
_cell_measurement_reflns_used    550
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      24.965
_cell_measurement_theta_min      2.306
_cell_volume                     2009.4(18)
_computing_cell_refinement       'BRUKER APEX II'
_computing_data_collection       'BRUKER APEX II'
_computing_data_reduction        SAINT
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3(Sheldrick, 2018)'
_computing_structure_solution    'SHELXT 2014/4 (Sheldrick, 2014)'
_diffrn_ambient_temperature      295.77
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_device_type  'BRUKER APEX II'
_diffrn_measurement_method       'Omega scan'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.1978
_diffrn_reflns_av_unetI/netI     0.0852
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            48488
_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_theta_full        24.965
_diffrn_reflns_theta_max         24.965
_diffrn_reflns_theta_min         2.306
_exptl_absorpt_coefficient_mu    6.648
_exptl_absorpt_correction_T_max  0.323
_exptl_absorpt_correction_T_min  0.161
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2014/5 (Bruker,2014/5) was used for absorption correction.
wR2(int) was 0.1464 before and 0.0811 after correction.
The Ratio of minimum to maximum transmission is 0.4327.
The \l/2 correction factor is Not present.
;
_exptl_crystal_colour            BROWN
_exptl_crystal_density_diffrn    1.902
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       BLOCK
_exptl_crystal_F_000             1133
_exptl_crystal_size_max          0.31
_exptl_crystal_size_mid          0.24
_exptl_crystal_size_min          0.17
_exptl_transmission_factor_max   0.323
_exptl_transmission_factor_min   0.161
_refine_diff_density_max         1.204
_refine_diff_density_min         -1.026
_refine_diff_density_rms         0.169
_refine_ls_extinction_coef       0.0022(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   1.121
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     457
_refine_ls_number_reflns         7032
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.121
_refine_ls_R_factor_all          0.0891
_refine_ls_R_factor_gt           0.0631
_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^)+(0.0549P)^2^+11.2536P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1487
_refine_ls_wR_factor_ref         0.1708
_reflns_Friedel_coverage         0.000
_reflns_number_gt                5387
_reflns_number_total             7032
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d0nj05635a2.cif
_cod_data_source_block           2
_cod_depositor_comments
'Adding full bibliography for 7060264--7060265.cif.'
_cod_database_code               7060265
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All N(H) groups, All N(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups, All O(H) groups, All O(H,H) groups
2. Others
 Sof(Br6)=1-FVAR(1)
 Sof(Br3)=Sof(Zn3)=Sof(Br5)=Sof(Br4)=FVAR(1)
3.a Free rotating group:
 O4(H4A,H4B)
3.b Ternary CH refined with riding coordinates:
 N3(H3), C30(H30), C15(H15), C22(H22), C7(H7)
3.c Secondary CH2 refined with riding coordinates:
 N6(H6A,H6B), C12(H12A,H12B), C26(H26A,H26B), C27(H27A,H27B), C28(H28A,H28B),
 C13(H13A,H13B), C11(H11A,H11B), C14(H14A,H14B), C29(H29A,H29B)
3.d Aromatic/amide H refined with riding coordinates:
 C19(H19), C25(H25), C17(H17), C10(H10), C6(H6), C2(H2)
3.e Idealised Me refined as rotating group:
 C8(H8A,H8B,H8C), C24(H24A,H24B,H24C), C23(H23A,H23B,H23C), C9(H9A,H9B,H9C),
 C31(H31A,H31B,H31C)
3.f Idealised tetrahedral OH refined as rotating group:
 O3(H3A)
;
_shelx_shelxl_version_number     2018/3
_olex2_submission_special_instructions 'No special instructions were received'