Piperidine and piperazine analogs in action: zinc(ii)-mediated formation of amidines
Podjed, Nina; Košmrlj, Janez; Modec, Barbara; New Journal of Chemistry 48 (2024) 8844–8859; doi:10.1039/D4NJ00235K

data_7063169
_publ_section_title
;
 Piperidine and piperazine analogs in action: zinc(ii)-mediated formation
 of amidines
;
_journal_issue                   19
_journal_name_full               'New Journal of Chemistry'
_journal_page_first              8844
_journal_page_last               8859
_journal_paper_doi               10.1039/D4NJ00235K
_journal_volume                  48
_journal_year                    2024
_chemical_formula_moiety         'C40 H40 N6 O4 Zn, 2(C2 H5 N O)'
_chemical_formula_sum            'C44 H50 N8 O6 Zn'
_chemical_formula_weight         852.29
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2ybc'
_space_group_name_H-M_alt        'P 1 21/c 1'
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     dual
_audit_creation_date             2022-05-05
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_audit_update_record
;
2022-06-25 deposited with the CCDC.	2024-04-16 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 115.978(2)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   11.2690(2)
_cell_length_b                   17.3987(3)
_cell_length_c                   11.4134(2)
_cell_measurement_reflns_used    31194
_cell_measurement_temperature    150.00(10)
_cell_measurement_theta_max      30.1650
_cell_measurement_theta_min      3.0430
_cell_volume                     2011.68(7)
_computing_cell_refinement       'CrysAlisPro 1.171.40.68a (Rigaku OD, 2019)'
_computing_data_collection       'CrysAlisPro 1.171.40.68a (Rigaku OD, 2019)'
_computing_data_reduction        'CrysAlisPro 1.171.40.68a (Rigaku OD, 2019)'
_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    'ShelXT (Sheldrick, 2015)'
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      150.00(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 10.4933
_diffrn_detector_type            Atlas
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.972
_diffrn_measurement_details
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  t~exp~   \w     \q     \k     \f   Frames
  1  \w    -62.00  40.00   1.00    3.50    --   14.21 -37.00 -30.00  102
  2  \w     39.00 104.00   1.00    3.50    --   14.21 178.00-180.00   65
  3  \w    -15.00  88.00   1.00    3.50    --   14.21  57.00-180.00  103
  4  \w    -62.00  40.00   1.00    3.50    --   14.21 -37.00 120.00  102
  5  \w    -12.00  90.00   1.00    3.50    --   14.21  37.00  90.00  102
  6  \w    -15.00  56.00   1.00    3.50    --   14.21 -99.00 -90.00   71
  7  \w    -12.00  90.00   1.00    3.50    --   14.21  37.00 -60.00  102
  8  \w    -42.00  19.00   1.00    3.50    --  -14.52 -77.00 -90.00   61
  9  \w    -74.00 -30.00   1.00    3.50    --  -14.52 128.00 -67.87   44
 10  \w    -92.00 -43.00   1.00    3.50    --  -14.52 154.00  20.60   49
 11  \w    -48.00  21.00   1.00    3.50    --  -14.52  77.00 -60.00   69
 12  \w    -84.00 -37.00   1.00    3.50    --  -14.52 145.00-155.00   47
 13  \w    -92.00 -43.00   1.00    3.50    --  -14.52 154.00  -3.93   49
 14  \w    -42.00  19.00   1.00    3.50    --  -14.52 -77.00-180.00   61
 15  \w    -77.00 -33.00   1.00    3.50    --  -14.52 133.00 122.48   44
 16  \w    -74.00 -30.00   1.00    3.50    --  -14.52 128.00 100.75   44
 17  \w    -96.00  32.00   1.00    3.50    --  -14.52 -19.00 150.00  128
 18  \w    -86.00 -38.00   1.00    3.50    --  -14.52 147.00 143.00   48
 19  \w    -32.00  30.00   1.00    3.50    --   14.21  19.00-120.00   62
 20  \w    -62.00  40.00   1.00    3.50    --   14.21 -37.00  30.00  102
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at home/near, Atlas'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0053878000
_diffrn_orient_matrix_UB_12      -0.0406490000
_diffrn_orient_matrix_UB_13      -0.0025921000
_diffrn_orient_matrix_UB_21      -0.0357768000
_diffrn_orient_matrix_UB_22      0.0014586000
_diffrn_orient_matrix_UB_23      0.0378978000
_diffrn_orient_matrix_UB_31      -0.0599380000
_diffrn_orient_matrix_UB_32      0.0027940000
_diffrn_orient_matrix_UB_33      -0.0577586000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0348
_diffrn_reflns_av_unetI/netI     0.0169
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.972
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_k_max       24
_diffrn_reflns_limit_k_min       -24
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            78590
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.972
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         30.348
_diffrn_reflns_theta_min         2.326
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    0.671
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.79579
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.40.68a (Rigaku Oxford Diffraction, 2019)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.407
_exptl_crystal_description       block
_exptl_crystal_F_000             896
_exptl_crystal_size_max          0.5
_exptl_crystal_size_mid          0.4
_exptl_crystal_size_min          0.25
_refine_diff_density_max         0.407
_refine_diff_density_min         -0.254
_refine_diff_density_rms         0.051
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.038
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     281
_refine_ls_number_reflns         5875
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.038
_refine_ls_R_factor_all          0.0384
_refine_ls_R_factor_gt           0.0297
_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^)+(0.0340P)^2^+1.0241P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0731
_refine_ls_wR_factor_ref         0.0791
_reflns_Friedel_coverage         0.000
_reflns_number_gt                5038
_reflns_number_total             5875
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d4nj00235k2.cif
_cod_data_source_block           18b
_cod_depositor_comments
'Adding full bibliography for 7063150--7063171.cif.'
_cod_database_code               7063169
_shelx_shelxl_version_number     2018/3
_shelx_estimated_absorpt_t_max   0.850
_shelx_estimated_absorpt_t_min   0.730
_reflns_odcompleteness_completeness 99.88
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     27.50
_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 Secondary CH2 refined with riding coordinates:
 C20(H20A,H20B), C21(H21A,H21B), C22(H22A,H22B), C23(H23A,H23B)
2.b Aromatic/amide H refined with riding coordinates:
 C11(H11), C12(H12), C13(H13), C14(H14), C16(H16), C17(H17), C25(H25),
 C26(H26), C27(H27), C28(H28), C29(H29)
2.c Idealised Me refined as rotating group:
 C32(H32A,H32B,H32C)
;
_shelx_res_checksum              16922
_oxdiff_exptl_absorpt_empirical_details
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.253
_oxdiff_exptl_absorpt_empirical_full_min 0.780