#------------------------------------------------------------------------------
#$Date: 2024-07-05 20:40:40 +0300 (Fri, 05 Jul 2024) $
#$Revision: 293205 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/06/31/7063165.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/
#
# All data on this site have been placed in the public domain by the
# contributors.
#
data_7063165
loop_
_publ_author_name
'Podjed, Nina'
'Košmrlj, Janez'
'Modec, Barbara'
_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      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             2022-05-05
_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                101.629(4)
_cell_angle_beta                 101.475(3)
_cell_angle_gamma                101.582(3)
_cell_formula_units_Z            1
_cell_length_a                   7.9641(2)
_cell_length_b                   10.7052(4)
_cell_length_c                   12.7812(5)
_cell_measurement_reflns_used    7996
_cell_measurement_temperature    150.00(10)
_cell_measurement_theta_max      30.0410
_cell_measurement_theta_min      2.9250
_cell_volume                     1012.52(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 0.904
_diffrn_measurement_details
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -67.00  60.00   1.00    5.00    --   14.05 -19.00  30.00  127
  2  ω    -12.00  87.00   1.00    5.00    --   14.05  37.00 -90.00   99
  3  ω    -12.00  90.00   1.00    5.00    --   14.05  37.00-180.00  102
  4  ω    -15.00  56.00   1.00    5.00    --   14.05 -99.00   0.00   71
  5  ω    -12.00  89.00   1.00    5.00    --   14.05  37.00  60.00  101
  6  ω    -40.00  48.00   1.00    5.00    --   14.05 -77.00-120.00   88
  7  ω    -48.00  -1.00   1.00    5.00    --  -14.36  77.00-180.00   47
  8  ω    -89.00 -60.00   1.00    5.00    --  -14.36 151.00  -7.39   29
  9  ω    -32.00  18.00   1.00    5.00    --  -14.36 -77.00-120.00   50
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at home/near, Atlas'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0254171000
_diffrn_orient_matrix_UB_12      -0.0155234000
_diffrn_orient_matrix_UB_13      -0.0584580000
_diffrn_orient_matrix_UB_21      -0.0279547000
_diffrn_orient_matrix_UB_22      0.0591578000
_diffrn_orient_matrix_UB_23      0.0023721000
_diffrn_orient_matrix_UB_31      0.0859438000
_diffrn_orient_matrix_UB_32      0.0338064000
_diffrn_orient_matrix_UB_33      -0.0005697000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0358
_diffrn_reflns_av_unetI/netI     0.0361
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.904
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            20001
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.904
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         30.371
_diffrn_reflns_theta_min         2.696
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    0.667
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.95894
_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    1.398
_exptl_crystal_description       block
_exptl_crystal_F_000             448
_exptl_crystal_size_max          0.25
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.1
_refine_diff_density_max         0.339
_refine_diff_density_min         -0.385
_refine_diff_density_rms         0.056
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.057
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     281
_refine_ls_number_reflns         5524
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.057
_refine_ls_R_factor_all          0.0412
_refine_ls_R_factor_gt           0.0335
_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/[σ²(Fo²)+(0.0280P)²+0.4458P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0748
_refine_ls_wR_factor_ref         0.0801
_reflns_Friedel_coverage         0.000
_reflns_number_gt                4918
_reflns_number_total             5524
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d4nj00235k2.cif
_cod_data_source_block           18a
_cod_depositor_comments
'Adding full bibliography for 7063150--7063171.cif.'
_cod_original_cell_volume        1012.52(6)
_cod_database_code               7063165
_shelx_shelxl_version_number     2018/3
_shelx_space_group_comment
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_shelx_estimated_absorpt_t_max   0.936
_shelx_estimated_absorpt_t_min   0.851
_reflns_odcompleteness_completeness 99.87
_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)
;
_oxdiff_exptl_absorpt_empirical_details
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.156
_oxdiff_exptl_absorpt_empirical_full_min 0.890
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Zn1 Zn 0.000000 0.500000 0.500000 0.01607(7) Uani 1 2 d S T P . .
O1 O 0.22029(12) 0.60396(10) 0.46595(8) 0.0190(2) Uani 1 1 d . . . . .
O3 O 0.98727(14) 1.14024(11) 0.59911(11) 0.0318(3) Uani 1 1 d . . . . .
O11 O 0.44779(14) 0.78162(11) 0.53308(10) 0.0314(3) Uani 1 1 d . . . . .
N1 N 0.05893(15) 0.69788(11) 0.62275(9) 0.0169(2) Uani 1 1 d . . . . .
N2 N 0.15900(15) 0.42194(12) 0.61921(10) 0.0166(2) Uani 1 1 d . . . . .
H2 H 0.105(2) 0.3450(18) 0.6030(14) 0.020(4) Uiso 1 1 d . . . . .
N3 N 0.78889(18) 0.94422(13) 0.53934(12) 0.0268(3) Uani 1 1 d . . . . .
H3A H 0.853(3) 0.916(2) 0.4968(17) 0.036(5) Uiso 1 1 d . . . . .
H3B H 0.693(3) 0.894(2) 0.5425(16) 0.035(5) Uiso 1 1 d . . . . .
N22 N 0.43966(15) 0.41419(12) 0.80084(9) 0.0177(2) Uani 1 1 d . . . . .
C10 C -0.02596(18) 0.74885(14) 0.69879(11) 0.0178(3) Uani 1 1 d . . . . .
C11 C -0.18064(19) 0.66827(15) 0.71164(12) 0.0218(3) Uani 1 1 d . . . . .
H11 H -0.224932 0.582386 0.668095 0.026 Uiso 1 1 calc R . . . .
C12 C -0.2654(2) 0.71657(16) 0.78821(13) 0.0271(3) Uani 1 1 d . . . . .
H12 H -0.366194 0.662697 0.796979 0.033 Uiso 1 1 calc R . . . .
C13 C -0.2014(2) 0.84686(17) 0.85363(13) 0.0297(3) Uani 1 1 d . . . . .
H13 H -0.260861 0.878605 0.904779 0.036 Uiso 1 1 calc R . . . .
C14 C -0.0532(2) 0.92690(16) 0.84271(13) 0.0273(3) Uani 1 1 d . . . . .
H14 H -0.012768 1.013116 0.885898 0.033 Uiso 1 1 calc R . . . .
C15 C 0.03966(19) 0.87948(15) 0.76587(12) 0.0221(3) Uani 1 1 d . . . . .
C16 C 0.1965(2) 0.95655(16) 0.75361(14) 0.0295(3) Uani 1 1 d . . . . .
H16 H 0.242558 1.042900 0.795930 0.035 Uiso 1 1 calc R . . . .
C17 C 0.2803(2) 0.90377(16) 0.67942(14) 0.0285(3) Uani 1 1 d . . . . .
H17 H 0.385077 0.953192 0.671405 0.034 Uiso 1 1 calc R . . . .
C18 C 0.20693(18) 0.77369(14) 0.61495(12) 0.0200(3) Uani 1 1 d . . . . .
C19 C 0.30079(18) 0.71536(14) 0.53107(12) 0.0197(3) Uani 1 1 d . . . . .
C20 C 0.16640(18) 0.47632(15) 0.73605(11) 0.0198(3) Uani 1 1 d . . . . .
H20A H 0.046725 0.469701 0.744363 0.024 Uiso 1 1 calc R . . . .
H20B H 0.227814 0.568992 0.757316 0.024 Uiso 1 1 calc R . . . .
C21 C 0.25947(18) 0.40627(15) 0.81332(12) 0.0196(3) Uani 1 1 d . . . . .
H21A H 0.263127 0.447121 0.889000 0.023 Uiso 1 1 calc R . . . .
H21B H 0.194600 0.314689 0.796113 0.023 Uiso 1 1 calc R . . . .
C22 C 0.43606(18) 0.35529(15) 0.68563(11) 0.0198(3) Uani 1 1 d . . . . .
H22A H 0.377027 0.262233 0.666235 0.024 Uiso 1 1 calc R . . . .
H22B H 0.556321 0.363537 0.678057 0.024 Uiso 1 1 calc R . . . .
C23 C 0.34003(18) 0.42241(15) 0.60750(12) 0.0202(3) Uani 1 1 d . . . . .
H23A H 0.407595 0.512803 0.621427 0.024 Uiso 1 1 calc R . . . .
H23B H 0.333669 0.378033 0.532207 0.024 Uiso 1 1 calc R . . . .
C24 C 0.55101(18) 0.36832(14) 0.87758(11) 0.0188(3) Uani 1 1 d . . . . .
C25 C 0.4906(2) 0.30153(15) 0.95122(12) 0.0237(3) Uani 1 1 d . . . . .
H25 H 0.372367 0.287532 0.953254 0.028 Uiso 1 1 calc R . . . .
C26 C 0.6070(2) 0.25563(17) 1.02189(13) 0.0300(3) Uani 1 1 d . . . . .
H26 H 0.565219 0.210728 1.070441 0.036 Uiso 1 1 calc R . . . .
C27 C 0.7832(2) 0.27589(18) 1.02079(13) 0.0307(4) Uani 1 1 d . . . . .
H27 H 0.859518 0.243359 1.067025 0.037 Uiso 1 1 calc R . . . .
C28 C 0.8447(2) 0.34523(18) 0.94999(13) 0.0294(4) Uani 1 1 d . . . . .
H28 H 0.963704 0.360672 0.949528 0.035 Uiso 1 1 calc R . . . .
C29 C 0.73113(19) 0.39177(16) 0.87994(12) 0.0244(3) Uani 1 1 d . . . . .
H29 H 0.775025 0.439426 0.833650 0.029 Uiso 1 1 calc R . . . .
C31 C 0.84739(19) 1.06592(15) 0.60159(13) 0.0238(3) Uani 1 1 d . . . . .
C32 C 0.7383(2) 1.11313(19) 0.67635(16) 0.0374(4) Uani 1 1 d . . . . .
H32A H 0.806764 1.193364 0.729092 0.056 Uiso 1 1 calc GR . . . .
H32B H 0.703456 1.047399 0.714366 0.056 Uiso 1 1 calc GR . . . .
H32C H 0.634789 1.128950 0.633588 0.056 Uiso 1 1 calc GR . . . .
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Zn Zn 0.2839 1.4301 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
O1 Zn1 O1 180.0 2_566 . ?
O1 Zn1 N1 77.92(4) 2_566 2_566 ?
O1 Zn1 N1 102.08(4) . 2_566 ?
O1 Zn1 N1 102.07(4) 2_566 . ?
O1 Zn1 N1 77.92(4) . . ?
O1 Zn1 N2 92.51(4) 2_566 2_566 ?
O1 Zn1 N2 87.49(4) 2_566 . ?
O1 Zn1 N2 87.49(4) . 2_566 ?
O1 Zn1 N2 92.51(4) . . ?
N1 Zn1 N1 180.0 . 2_566 ?
N2 Zn1 N1 91.95(4) 2_566 2_566 ?
N2 Zn1 N1 88.05(4) 2_566 . ?
N2 Zn1 N1 91.95(4) . . ?
N2 Zn1 N1 88.05(4) . 2_566 ?
N2 Zn1 N2 180.0 2_566 . ?
C19 O1 Zn1 117.67(9) . . ?
C10 N1 Zn1 133.10(9) . . ?
C18 N1 Zn1 108.77(9) . . ?
C18 N1 C10 118.12(12) . . ?
C20 N2 Zn1 115.79(8) . . ?
C20 N2 C23 109.15(11) . . ?
C23 N2 Zn1 115.79(9) . . ?
C21 N22 C22 110.28(11) . . ?
C24 N22 C21 116.21(11) . . ?
C24 N22 C22 112.70(11) . . ?
N1 C10 C11 119.24(13) . . ?
N1 C10 C15 121.57(13) . . ?
C11 C10 C15 119.18(13) . . ?
C12 C11 C10 120.11(14) . . ?
C11 C12 C13 120.60(15) . . ?
C14 C13 C12 120.57(14) . . ?
C13 C14 C15 120.34(15) . . ?
C14 C15 C10 119.18(14) . . ?
C16 C15 C10 118.10(14) . . ?
C16 C15 C14 122.72(14) . . ?
C17 C16 C15 119.52(14) . . ?
C16 C17 C18 119.33(14) . . ?
N1 C18 C17 123.35(14) . . ?
N1 C18 C19 117.57(12) . . ?
C17 C18 C19 119.09(13) . . ?
O1 C19 C18 117.06(12) . . ?
O11 C19 O1 126.23(14) . . ?
O11 C19 C18 116.72(13) . . ?
N2 C20 C21 113.15(12) . . ?
N22 C21 C20 109.59(11) . . ?
N22 C22 C23 111.06(11) . . ?
N2 C23 C22 112.83(11) . . ?
C25 C24 N22 123.46(13) . . ?
C25 C24 C29 118.15(13) . . ?
C29 C24 N22 118.38(13) . . ?
C24 C25 C26 120.21(14) . . ?
C27 C26 C25 120.92(15) . . ?
C26 C27 C28 119.06(15) . . ?
C29 C28 C27 120.60(15) . . ?
C28 C29 C24 120.98(15) . . ?
O3 C31 N3 122.15(15) . . ?
O3 C31 C32 120.32(15) . . ?
N3 C31 C32 117.53(14) . . ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Zn1 O1 2.0545(9) 2_566 ?
Zn1 O1 2.0545(9) . ?
Zn1 N1 2.2665(12) 2_566 ?
Zn1 N1 2.2665(12) . ?
Zn1 N2 2.1894(12) 2_566 ?
Zn1 N2 2.1894(12) . ?
O1 C19 1.2674(17) . ?
O3 C31 1.2423(18) . ?
O11 C19 1.2335(17) . ?
N1 C10 1.3767(18) . ?
N1 C18 1.3240(18) . ?
N2 C20 1.4741(18) . ?
N2 C23 1.4780(17) . ?
N3 C31 1.318(2) . ?
N22 C21 1.4628(17) . ?
N22 C22 1.4726(17) . ?
N22 C24 1.4186(18) . ?
C10 C11 1.414(2) . ?
C10 C15 1.417(2) . ?
C11 C12 1.371(2) . ?
C12 C13 1.407(2) . ?
C13 C14 1.362(2) . ?
C14 C15 1.417(2) . ?
C15 C16 1.408(2) . ?
C16 C17 1.361(2) . ?
C17 C18 1.407(2) . ?
C18 C19 1.528(2) . ?
C20 C21 1.5224(19) . ?
C22 C23 1.5180(19) . ?
C24 C25 1.393(2) . ?
C24 C29 1.399(2) . ?
C25 C26 1.395(2) . ?
C26 C27 1.380(2) . ?
C27 C28 1.382(2) . ?
C28 C29 1.381(2) . ?
C31 C32 1.495(2) . ?
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
_geom_hbond_publ_flag
N2 H2 O3 0.813(18) 2.190(18) 2.9871(17) 166.7(17) 1_445 yes
N3 H3A O3 0.87(2) 2.03(2) 2.8955(19) 177.2(19) 2_776 yes
N3 H3B O11 0.85(2) 2.05(2) 2.8939(17) 172.7(19) . yes
