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_7063160
_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         'C30 H36 N6 O4 Zn, 0.5(C2 H3 N)'
_chemical_formula_sum            'C31 H37.5 N6.5 O4 Zn'
_chemical_formula_weight         630.54
_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             2022-05-04
_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                78.682(2)
_cell_angle_beta                 87.613(2)
_cell_angle_gamma                86.401(2)
_cell_formula_units_Z            4
_cell_length_a                   10.4192(2)
_cell_length_b                   14.5738(4)
_cell_length_c                   20.2693(5)
_cell_measurement_reflns_used    17768
_cell_measurement_temperature    150.00(10)
_cell_measurement_theta_max      30.0760
_cell_measurement_theta_min      2.4660
_cell_volume                     3010.68(13)
_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 0.905
_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   25.00    --   14.21  57.00  90.00  103
  2  \w    -15.00  77.00   1.00   25.00    --   14.21  57.00 -30.00   92
  3  \w    -42.00  48.00   1.00   25.00    --   14.21 -77.00 -60.00   90
  4  \w    -13.00  56.00   1.00   25.00    --   14.21 -99.00  60.00   69
  5  \w    -12.00  90.00   1.00   25.00    --   14.21  37.00   0.00  102
  6  \w    -12.00  90.00   1.00   25.00    --   14.21  37.00-120.00  102
  7  \w    -42.00  48.00   1.00   25.00    --   14.21 -77.00-150.00   90
  8  \w     51.00  91.00   1.00   25.00    --   14.21 178.00-120.00   40
  9  \w    -92.00 -65.00   1.00   25.00    --  -14.52 154.00  71.34   27
;
_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      0.0088930000
_diffrn_orient_matrix_UB_12      0.0415823000
_diffrn_orient_matrix_UB_13      -0.0242051000
_diffrn_orient_matrix_UB_21      -0.0126650000
_diffrn_orient_matrix_UB_22      0.0270483000
_diffrn_orient_matrix_UB_23      0.0253061000
_diffrn_orient_matrix_UB_31      0.0664632000
_diffrn_orient_matrix_UB_32      -0.0032539000
_diffrn_orient_matrix_UB_33      0.0069624000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0294
_diffrn_reflns_av_unetI/netI     0.0302
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.905
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       20
_diffrn_reflns_limit_k_min       -20
_diffrn_reflns_limit_l_max       28
_diffrn_reflns_limit_l_min       -28
_diffrn_reflns_number            59679
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.905
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         30.363
_diffrn_reflns_theta_min         2.359
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    0.863
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.81565
_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    1.391
_exptl_crystal_description       block
_exptl_crystal_F_000             1324
_exptl_crystal_size_max          0.4
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.1
_refine_diff_density_max         0.400
_refine_diff_density_min         -0.357
_refine_diff_density_rms         0.055
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.024
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     790
_refine_ls_number_reflns         16415
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.024
_refine_ls_R_factor_all          0.0501
_refine_ls_R_factor_gt           0.0330
_refine_ls_shift/su_max          0.003
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0408P)^2^+0.8878P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0807
_refine_ls_wR_factor_ref         0.0899
_reflns_Friedel_coverage         0.000
_reflns_number_gt                12708
_reflns_number_total             16415
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d4nj00235k2.cif
_cod_data_source_block           11
_cod_depositor_comments
'Adding full bibliography for 7063150--7063171.cif.'
_cod_original_formula_sum        'C31 H37.50 N6.50 O4 Zn'
_cod_database_code               7063160
_shelx_shelxl_version_number     2018/3
_shelx_estimated_absorpt_t_max   0.919
_shelx_estimated_absorpt_t_min   0.724
_reflns_odcompleteness_completeness 99.82
_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:
 C31(H31A,H31B), C32(H32A,H32B), C33(H33A,H33B), C34(H34A,H34B), C41(H41A,
 H41B), C42(H42A,H42B), C43(H43A,H43B), C44(H44A,H44B), C61(H61A,H61B),
 C62(H62A,H62B), C63(H63A,H63B), C64(H64A,H64B), C81(H81A,H81B), C82(H82A,H82B),
  C83(H83A,H83B), C84(H84A,H84B)
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), C51(H51), C52(H52), C53(H53),
  C54(H54), C56(H56), C57(H57), C71(H71), C72(H72), C73(H73), C74(H74),
 C76(H76), C77(H77)
2.c Idealised Me refined as rotating group:
 C35(H35A,H35B,H35C), C45(H45A,H45B,H45C), C65(H65A,H65B,H65C), C85(H85A,H85B,
 H85C), C92(H92A,H92B,H92C)
;
_shelx_res_checksum              32669
_oxdiff_exptl_absorpt_empirical_details
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.317
_oxdiff_exptl_absorpt_empirical_full_min 0.637