#------------------------------------------------------------------------------
#$Date: 2023-01-06 11:55:15 +0200 (Fri, 06 Jan 2023) $
#$Revision: 280205 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/06/20/7062098.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_7062098
loop_
_publ_author_name
'Podjed, Nina'
'Modec, Barbara'
_publ_section_title
;
 Amidines from cyclic amines and nitriles in the presence of zinc(ii):
 other nitriles in place of acetonitrile
;
_journal_issue                   48
_journal_name_full               'New Journal of Chemistry'
_journal_page_first              23225
_journal_page_last               23238
_journal_paper_doi               10.1039/D2NJ04668G
_journal_volume                  46
_journal_year                    2022
_chemical_formula_moiety         'C24 H21 N3 O4 Zn'
_chemical_formula_sum            'C24 H21 N3 O4 Zn'
_chemical_formula_weight         480.81
_space_group_crystal_system      monoclinic
_space_group_IT_number           15
_space_group_name_Hall           '-C 2yc'
_space_group_name_H-M_alt        'C 1 2/c 1'
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     dual
_audit_creation_date             2022-10-27
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_audit_update_record
;
2022-10-28 deposited with the CCDC.	2022-11-18 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 105.783(3)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   13.7196(4)
_cell_length_b                   8.0117(2)
_cell_length_c                   19.1729(5)
_cell_measurement_reflns_used    15326
_cell_measurement_temperature    150.00(10)
_cell_measurement_theta_max      30.1430
_cell_measurement_theta_min      2.9540
_cell_volume                     2027.98(10)
_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 0.960
_diffrn_measurement_details
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -42.00  48.00   1.00    6.00    --   14.21 -77.00 -90.00   90
  2  ω    -42.00  48.00   1.00    6.00    --   14.21 -77.00 150.00   90
  3  ω    -15.00  88.00   1.00    6.00    --   14.21  57.00  60.00  103
  4  ω    -15.00  88.00   1.00    6.00    --   14.21  57.00 -60.00  103
  5  ω    -12.00  90.00   1.00    6.00    --   14.21  37.00-150.00  102
  6  ω     39.00 104.00   1.00    6.00    --   14.21 178.00  60.00   65
  7  ω    -48.00  21.00   1.00    6.00    --  -14.52  77.00  60.00   69
  8  ω    -42.00  19.00   1.00    6.00    --  -14.52 -77.00  30.00   61
  9  ω    -77.00 -33.00   1.00    6.00    --  -14.52 133.00-170.05   44
 10  ω    -42.00  48.00   1.00    6.00    --   14.21 -77.00  60.00   90
 11  ω     14.00  81.00   1.00    6.00    --   14.21-141.00 165.00   67
 12  ω    -77.00 -33.00   1.00    6.00    --  -14.52 133.00 120.35   44
 13  ω    -48.00  21.00   1.00    6.00    --  -14.52  77.00-150.00   69
 14  ω    -81.00 -40.00   1.00    6.00    --  -14.52 141.00-136.00   41
 15  ω    -76.00 -30.00   1.00    6.00    --  -14.52 131.00 -51.00   46
;
_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      -0.0240692000
_diffrn_orient_matrix_UB_12      0.0144019000
_diffrn_orient_matrix_UB_13      -0.0372047000
_diffrn_orient_matrix_UB_21      0.0281723000
_diffrn_orient_matrix_UB_22      -0.0662815000
_diffrn_orient_matrix_UB_23      -0.0095249000
_diffrn_orient_matrix_UB_31      -0.0389103000
_diffrn_orient_matrix_UB_32      -0.0568933000
_diffrn_orient_matrix_UB_33      0.0016812000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0338
_diffrn_reflns_av_unetI/netI     0.0152
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.960
_diffrn_reflns_limit_h_max       18
_diffrn_reflns_limit_h_min       -19
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       26
_diffrn_reflns_limit_l_min       -27
_diffrn_reflns_number            29139
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.960
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         30.306
_diffrn_reflns_theta_min         2.974
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    1.250
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.81445
_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    1.575
_exptl_crystal_description       block
_exptl_crystal_F_000             992
_exptl_crystal_size_max          0.4
_exptl_crystal_size_mid          0.4
_exptl_crystal_size_min          0.1
_refine_diff_density_max         0.372
_refine_diff_density_min         -0.418
_refine_diff_density_rms         0.058
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.062
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     172
_refine_ls_number_reflns         2929
_refine_ls_number_restraints     30
_refine_ls_restrained_S_all      1.059
_refine_ls_R_factor_all          0.0258
_refine_ls_R_factor_gt           0.0243
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0346P)²+1.6178P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0652
_refine_ls_wR_factor_ref         0.0663
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2815
_reflns_number_total             2929
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d2nj04668g2.cif
_cod_data_source_block           3
_cod_depositor_comments
'Adding full bibliography for 7062097--7062109.cif.'
_cod_database_code               7062098
_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   0.885
_shelx_estimated_absorpt_t_min   0.635
_reflns_odcompleteness_completeness 99.92
_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
2. Rigid body (RIGU) restrains
 N2, C21, C22, C23, C24
 with sigma for 1-2 distances of 0.004 and sigma for 1-3 distances of 0.004
3. Others
 Fixed Sof: H2(0.5) N2(0.5) C21(0.5) H21A(0.5) H21B(0.5) C22(0.5) H22A(0.5)
 H22B(0.5) C23(0.5) H23A(0.5) H23B(0.5) C24(0.5) H24A(0.5) H24B(0.5)
4.a Secondary CH2 refined with riding coordinates:
 C21(H21A,H21B), C22(H22A,H22B), C23(H23A,H23B), C24(H24A,H24B)
4.b Aromatic/amide H refined with riding coordinates:
 C11(H11), C12(H12), C13(H13), C14(H14), C16(H16), C17(H17)
;
_oxdiff_exptl_absorpt_empirical_details
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.346
_oxdiff_exptl_absorpt_empirical_full_min 0.749
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y, -z+1/2'
'x+1/2, y+1/2, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y, z-1/2'
'-x+1/2, -y+1/2, -z'
'x+1/2, -y+1/2, z-1/2'
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 0.500000 0.23737(2) 0.750000 0.01734(7) Uani 1 2 d S T P . .
O1 O 0.39383(6) 0.16390(12) 0.79648(4) 0.02441(18) Uani 1 1 d . . . . .
O11 O 0.24291(7) 0.04204(17) 0.77853(5) 0.0379(3) Uani 1 1 d . . . . .
N1 N 0.38017(7) 0.15070(12) 0.65486(5) 0.01807(18) Uani 1 1 d . . . . .
C10 C 0.37783(8) 0.13872(14) 0.58281(6) 0.0188(2) Uani 1 1 d . . . . .
C11 C 0.45029(10) 0.22620(16) 0.55683(7) 0.0238(2) Uani 1 1 d . . . . .
H11 H 0.499807 0.289861 0.588437 0.029 Uiso 1 1 calc R . . . .
C12 C 0.44737(11) 0.21694(19) 0.48477(7) 0.0297(3) Uani 1 1 d . . . . .
H12 H 0.494751 0.275792 0.467843 0.036 Uiso 1 1 calc R . . . .
C13 C 0.37387(11) 0.11986(19) 0.43612(7) 0.0314(3) Uani 1 1 d . . . . .
H13 H 0.373127 0.115004 0.387509 0.038 Uiso 1 1 calc R . . . .
C14 C 0.30384(10) 0.03301(18) 0.45992(7) 0.0284(3) Uani 1 1 d . . . . .
H14 H 0.255671 -0.031252 0.427489 0.034 Uiso 1 1 calc R . . . .
C15 C 0.30387(9) 0.03990(16) 0.53390(6) 0.0228(2) Uani 1 1 d . . . . .
C16 C 0.23387(10) -0.04897(18) 0.56177(7) 0.0287(3) Uani 1 1 d . . . . .
H16 H 0.186079 -0.117932 0.531501 0.034 Uiso 1 1 calc R . . . .
C17 C 0.23634(9) -0.03369(18) 0.63311(7) 0.0278(3) Uani 1 1 d . . . . .
H17 H 0.190320 -0.091106 0.651959 0.033 Uiso 1 1 calc R . . . .
C18 C 0.31007(8) 0.07093(15) 0.67759(6) 0.0209(2) Uani 1 1 d . . . . .
C19 C 0.31460(9) 0.09350(17) 0.75743(6) 0.0236(2) Uani 1 1 d . . . . .
H2 H 0.407(3) 0.498(4) 0.7415(19) 0.035(9) Uiso 0.5 1 d . . . . .
N2 N 0.46956(14) 0.4854(2) 0.74800(11) 0.0181(4) Uani 0.5 1 d . U . A -1
C21 C 0.5168(10) 0.5872(13) 0.8144(6) 0.032(2) Uani 0.5 1 d . U . A -1
H21A H 0.481239 0.570417 0.851174 0.039 Uiso 0.5 1 calc R . . A -1
H21B H 0.587372 0.556937 0.834435 0.039 Uiso 0.5 1 calc R . . A -1
C22 C 0.5080(9) 0.7556(13) 0.7901(7) 0.062(3) Uani 0.5 1 d . U . A -1
H22A H 0.559742 0.822971 0.822483 0.075 Uiso 0.5 1 calc R . . A -1
H22B H 0.442299 0.799408 0.790781 0.075 Uiso 0.5 1 calc R . . A -1
C23 C 0.5195(7) 0.7651(12) 0.7154(6) 0.0365(13) Uani 0.5 1 d . U . A -1
H23A H 0.587968 0.795681 0.715654 0.044 Uiso 0.5 1 calc R . . A -1
H23B H 0.472232 0.844043 0.685950 0.044 Uiso 0.5 1 calc R . . A -1
C24 C 0.4937(9) 0.5784(10) 0.6878(5) 0.0220(14) Uani 0.5 1 d . U . A -1
H24A H 0.436266 0.576930 0.645125 0.026 Uiso 0.5 1 calc R . . A -1
H24B H 0.551265 0.528200 0.675614 0.026 Uiso 0.5 1 calc R . . A -1
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 145.63(6) 2_656 . ?
O1 Zn1 N1 90.47(3) . 2_656 ?
O1 Zn1 N1 90.47(3) 2_656 . ?
O1 Zn1 N1 78.81(4) . . ?
O1 Zn1 N1 78.81(3) 2_656 2_656 ?
O1 Zn1 N2 116.92(6) 2_656 . ?
O1 Zn1 N2 97.24(6) . . ?
N1 Zn1 N1 143.37(5) 2_656 . ?
N2 Zn1 N1 100.90(6) . . ?
N2 Zn1 N1 115.25(6) . 2_656 ?
C19 O1 Zn1 118.66(7) . . ?
C10 N1 Zn1 131.26(8) . . ?
C18 N1 Zn1 108.91(7) . . ?
C18 N1 C10 118.44(10) . . ?
N1 C10 C11 119.51(10) . . ?
N1 C10 C15 121.26(10) . . ?
C11 C10 C15 119.23(10) . . ?
C12 C11 C10 119.80(12) . . ?
C11 C12 C13 121.09(13) . . ?
C14 C13 C12 120.26(12) . . ?
C13 C14 C15 120.44(12) . . ?
C14 C15 C10 119.17(11) . . ?
C16 C15 C10 117.93(11) . . ?
C16 C15 C14 122.90(12) . . ?
C17 C16 C15 120.01(12) . . ?
C16 C17 C18 118.57(12) . . ?
N1 C18 C17 123.69(11) . . ?
N1 C18 C19 115.99(10) . . ?
C17 C18 C19 120.30(11) . . ?
O1 C19 C18 115.98(10) . . ?
O11 C19 O1 125.88(11) . . ?
O11 C19 C18 118.13(11) . . ?
C21 N2 Zn1 118.5(4) . . ?
C24 N2 Zn1 114.7(4) . . ?
C24 N2 C21 104.5(4) . . ?
C22 C21 N2 105.0(9) . . ?
C21 C22 C23 110.0(11) . . ?
C22 C23 C24 101.5(10) . . ?
N2 C24 C23 106.8(7) . . ?
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 1.9921(9) 2_656 ?
Zn1 O1 1.9921(9) . ?
Zn1 N1 2.2093(10) . ?
Zn1 N1 2.2092(9) 2_656 ?
Zn1 N2 2.0291(19) . ?
O1 C19 1.2718(16) . ?
O11 C19 1.2318(15) . ?
N1 C10 1.3764(14) . ?
N1 C18 1.3233(15) . ?
C10 C11 1.4132(17) . ?
C10 C15 1.4207(16) . ?
C11 C12 1.3733(17) . ?
C12 C13 1.407(2) . ?
C13 C14 1.362(2) . ?
C14 C15 1.4193(17) . ?
C15 C16 1.4122(18) . ?
C16 C17 1.3645(19) . ?
C17 C18 1.4085(18) . ?
C18 C19 1.5258(16) . ?
N2 C21 1.502(11) . ?
N2 C24 1.484(10) . ?
C21 C22 1.421(15) . ?
C22 C23 1.485(6) . ?
C23 C24 1.593(12) . ?
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 O11 0.84(4) 2.02(4) 2.856(2) 176(4) 4_556 yes
