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_7063159
_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         'C32 H29 N5 O4 Zn, C2 H3 N, 0.5[C10H14N2]'
_chemical_formula_sum            'C39 H39 N7 O4 Zn'
_chemical_formula_weight         735.14
_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
_atom_sites_solution_primary     dual
_audit_creation_date             2024-04-09
_audit_creation_method
;
Olex2 1.5
(compiled 2023.08.24 svn.re1ec1418 for OlexSys, GUI svn.r6817)
;
_audit_update_record
;
2024-04-09 deposited with the CCDC.	2024-04-16 downloaded from the CCDC.
;
_cell_angle_alpha                72.152(2)
_cell_angle_beta                 81.180(2)
_cell_angle_gamma                80.559(2)
_cell_formula_units_Z            2
_cell_length_a                   7.6458(2)
_cell_length_b                   15.0408(4)
_cell_length_c                   16.2179(4)
_cell_measurement_reflns_used    12991
_cell_measurement_temperature    150.00(10)
_cell_measurement_theta_max      29.9660
_cell_measurement_theta_min      2.8540
_cell_volume                     1740.66(8)
_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 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (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 0.909
_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    -15.00  88.00   1.00    7.50    --   14.21  57.00 120.00  103
  2  \w    -15.00  88.00   1.00    7.50    --   14.21  57.00   0.00  103
  3  \w    -15.00  88.00   1.00    7.50    --   14.21  57.00-120.00  103
  4  \w    -42.00  48.00   1.00    7.50    --   14.21 -77.00-150.00   90
  5  \w    -42.00  48.00   1.00    7.50    --   14.21 -77.00  90.00   90
  6  \w    -42.00  48.00   1.00    7.50    --   14.21 -77.00 -30.00   90
  7  \w    -72.00 -27.00   1.00    7.50    --  -14.52 125.00 162.60   45
  8  \w    -92.00 -43.00   1.00    7.50    --  -14.52 154.00-102.69   49
  9  \w    -92.00 -49.00   1.00    7.50    --  -14.52 154.00   1.77   43
;
_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      -0.0881840000
_diffrn_orient_matrix_UB_12      0.0031365000
_diffrn_orient_matrix_UB_13      -0.0101928000
_diffrn_orient_matrix_UB_21      -0.0289869000
_diffrn_orient_matrix_UB_22      -0.0185023000
_diffrn_orient_matrix_UB_23      0.0448883000
_diffrn_orient_matrix_UB_31      -0.0183177000
_diffrn_orient_matrix_UB_32      0.0462701000
_diffrn_orient_matrix_UB_33      0.0042431000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0354
_diffrn_reflns_av_unetI/netI     0.0346
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.909
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       21
_diffrn_reflns_limit_k_min       -21
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_number            34456
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.909
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         30.339
_diffrn_reflns_theta_min         2.628
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    0.758
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.98528
_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    1.403
_exptl_crystal_description       block
_exptl_crystal_F_000             768
_exptl_crystal_size_max          0.4
_exptl_crystal_size_mid          0.3
_exptl_crystal_size_min          0.15
_refine_diff_density_max         0.360
_refine_diff_density_min         -0.419
_refine_diff_density_rms         0.051
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.045
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     412
_refine_ls_number_reflns         9515
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.045
_refine_ls_R_factor_all          0.0407
_refine_ls_R_factor_gt           0.0319
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0378P)^2^+0.3878P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0788
_refine_ls_wR_factor_ref         0.0830
_reflns_Friedel_coverage         0.000
_reflns_number_gt                8029
_reflns_number_total             9515
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d4nj00235k2.cif
_cod_data_source_block           19
_cod_depositor_comments
'Adding full bibliography for 7063150--7063171.cif.'
_cod_database_code               7063159
_shelx_shelxl_version_number     2018/3
_shelx_estimated_absorpt_t_max   0.895
_shelx_estimated_absorpt_t_min   0.751
_reflns_odcompleteness_completeness 99.90
_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:
 C40(H40A,H40B), C41(H41A,H41B), C42(H42A,H42B), C43(H43A,H43B)
2.b Aromatic/amide H refined with riding coordinates:
 C11(H11), C12(H12), C13(H13), C14(H14), C16(H16), C17(H17), C21(H21),
 C22(H22), C23(H23), C24(H24), C26(H26), C27(H27), C45(H45), C46(H46), C47(H47),
  C48(H48), C49(H49)
2.c Idealised Me refined as rotating group:
 C32(H32A,H32B,H32C), C52(H52A,H52B,H52C)
;
_smtbx_masks_special_details
;
A solvent mask was calculated and 87 electrons were 
found in a volume of 336\%A^3^ in 1 void per unit cell. 
This is consistent with the presence of 
0.5[C10H14N2] per Asymmetric Unit 
which account for 88 electrons 
per unit cell.
;
_shelx_res_checksum              22588
_shelx_fab_checksum              64905
_oxdiff_exptl_absorpt_empirical_details
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.183
_oxdiff_exptl_absorpt_empirical_full_min 0.858