#------------------------------------------------------------------------------
#$Date: 2024-08-05 21:08:05 +0300 (Mon, 05 Aug 2024) $
#$Revision: 293768 $
#$URL: file:///home/coder/svn-repositories/cod/cif/1/57/18/1571890.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_1571890
loop_
_publ_author_name
'Trouvé, Jonathan'
'Delahaye, Vanessa'
'Tomasini, Michele'
'Rajeshwaran, Purushothaman'
'Roisnel, Thierry'
'Poater, Albert'
'Gramage-Doria, Rafael'
_publ_section_title
;
 Repurposing a supramolecular iridium catalyst via secondary
 Zn⋯O[double bond, length as m-dash]C weak interactions between the
 ligand and substrate leads to ortho-selective C(sp²)-H
 borylation of benzamides with unusual kinetics.
;
_journal_issue                   30
_journal_name_full               'Chemical science'
_journal_page_first              11794
_journal_page_last               11806
_journal_paper_doi               10.1039/d4sc01515k
_journal_volume                  15
_journal_year                    2024
_chemical_compound_source        'synthesis as described'
_chemical_formula_moiety         'C47 H35 N5 O Zn, C H2 Cl2'
_chemical_formula_sum            'C48 H37 Cl2 N5 O Zn'
_chemical_formula_weight         836.09
_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   geom
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   difmap
_audit_update_record
;
2022-10-28 deposited with the CCDC.	2024-06-11 downloaded from the CCDC.
;
_cell_angle_alpha                98.996(2)
_cell_angle_beta                 94.719(2)
_cell_angle_gamma                103.136(2)
_cell_formula_units_Z            2
_cell_length_a                   11.1934(5)
_cell_length_b                   12.5189(6)
_cell_length_c                   14.5833(6)
_cell_measurement_reflns_used    8431
_cell_measurement_temperature    150(2)
_cell_measurement_theta_max      27.40
_cell_measurement_theta_min      2.21
_cell_measurement_wavelength     0.71073
_cell_volume                     1950.79(15)
_computing_cell_refinement       'Bruker APEX2 (Bruker, 2014)'
_computing_data_collection       'Bruker APEX2 (Bruker, 2014)'
_computing_data_reduction        'Bruker APEX2 (Bruker, 2014)'
_computing_molecular_graphics
;
   'SXGRAPH (L. Farrugia, 1999), Mercury (CSD, 2020)'
;
_computing_publication_material  'CRYSCALC (T. Roisnel, local program, 2021)'
_computing_structure_refinement  'SHELXL-2018_3 (Sheldrick, 2018)'
_computing_structure_solution    'SHELXT (Sheldrick, 2015)'
_diffrn_ambient_temperature      150(2)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 8.33
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.992
_diffrn_measurement_device_type  'APEXII, Bruker-AXS'
_diffrn_measurement_method       'CCD rotation images, thin slices'
_diffrn_orient_matrix_UB_11      -0.0138416
_diffrn_orient_matrix_UB_12      -0.0760933
_diffrn_orient_matrix_UB_13      0.0164917
_diffrn_orient_matrix_UB_21      0.0742266
_diffrn_orient_matrix_UB_22      0.0265439
_diffrn_orient_matrix_UB_23      0.0481889
_diffrn_orient_matrix_UB_31      -0.0533200
_diffrn_orient_matrix_UB_32      0.0214392
_diffrn_orient_matrix_UB_33      0.0479499
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0296
_diffrn_reflns_av_unetI/netI     0.0405
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            21751
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.543
_diffrn_reflns_theta_min         2.406
_diffrn_source_current           30.
_diffrn_source_power             1500.0
_diffrn_source_voltage           50.
_exptl_absorpt_coefficient_mu    0.812
_exptl_absorpt_correction_T_max  0.843
_exptl_absorpt_correction_T_min  0.795
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
  [Sheldrick, G.M. (2014). SADABS Bruker AXS Inc., Madison, Wisconsin, USA]
;
_exptl_crystal_colour            red
_exptl_crystal_density_diffrn    1.423
_exptl_crystal_description       block
_exptl_crystal_F_000             864
_exptl_crystal_size_max          0.370
_exptl_crystal_size_mid          0.250
_exptl_crystal_size_min          0.210
_refine_diff_density_max         0.559
_refine_diff_density_min         -0.536
_refine_diff_density_rms         0.061
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.050
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     516
_refine_ls_number_reflns         8920
_refine_ls_number_restraints     6
_refine_ls_restrained_S_all      1.052
_refine_ls_R_factor_all          0.0462
_refine_ls_R_factor_gt           0.0371
_refine_ls_shift/su_max          0.016
_refine_ls_shift/su_mean         0.001
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0453P)²+0.6706P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0915
_refine_ls_wR_factor_ref         0.0961
_reflns_number_gt                7539
_reflns_number_total             8920
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            d4sc01515k2.cif
_cod_data_source_block           RG_GIA_022
_cod_depositor_comments          'Adding full bibliography for 1571890.cif.'
_cod_database_code               1571890
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 0.57107(2) 0.43779(2) 0.77875(2) 0.01674(7) Uani 1 1 d . . . . .
C1 C 0.69585(17) 0.25099(15) 0.70736(12) 0.0191(4) Uani 1 1 d . . . . .
C2 C 0.79887(17) 0.32579(16) 0.68562(13) 0.0196(4) Uani 1 1 d . . . . .
C3 C 0.82097(17) 0.44260(15) 0.70464(13) 0.0197(4) Uani 1 1 d . . . . .
C4 C 0.92894(17) 0.51834(16) 0.68374(14) 0.0238(4) Uani 1 1 d . . . . .
H4 H 0.995654 0.498429 0.654712 0.029 Uiso 1 1 calc R U . . .
C5 C 0.91730(17) 0.62311(16) 0.71327(14) 0.0230(4) Uani 1 1 d . . . . .
H5 H 0.974834 0.690554 0.709687 0.028 Uiso 1 1 calc R U . . .
C6 C 0.80132(16) 0.61304(15) 0.75110(12) 0.0188(4) Uani 1 1 d . . . . .
C7 C 0.75301(16) 0.70347(15) 0.78649(12) 0.0184(4) Uani 1 1 d . . . . .
C8 C 0.63993(16) 0.69421(15) 0.82282(12) 0.0185(4) Uani 1 1 d . . . . .
C9 C 0.58491(17) 0.78645(16) 0.84929(13) 0.0221(4) Uani 1 1 d . . . . .
H9 H 0.618511 0.862200 0.845355 0.027 Uiso 1 1 calc R U . . .
C10 C 0.47683(18) 0.74498(15) 0.88065(14) 0.0228(4) Uani 1 1 d . . . . .
H10 H 0.419875 0.785929 0.902605 0.027 Uiso 1 1 calc R U . . .
C11 C 0.46417(16) 0.62669(15) 0.87453(12) 0.0179(4) Uani 1 1 d . . . . .
C12 C 0.36455(16) 0.55246(15) 0.90142(12) 0.0185(4) Uani 1 1 d . . . . .
C13 C 0.35004(16) 0.43656(15) 0.89176(13) 0.0184(4) Uani 1 1 d . . . . .
C14 C 0.25372(17) 0.36269(16) 0.92728(14) 0.0229(4) Uani 1 1 d . . . . .
H14 H 0.192416 0.383626 0.962598 0.028 Uiso 1 1 calc R U . . .
C15 C 0.26691(17) 0.25799(16) 0.90093(14) 0.0229(4) Uani 1 1 d . . . . .
H15 H 0.216093 0.191405 0.913605 0.027 Uiso 1 1 calc R U . . .
C16 C 0.37290(16) 0.26651(15) 0.84987(13) 0.0188(4) Uani 1 1 d . . . . .
C17 C 0.41704(16) 0.17554(15) 0.80953(13) 0.0189(4) Uani 1 1 d . . . . .
C18 C 0.52275(17) 0.18307(15) 0.76331(13) 0.0191(4) Uani 1 1 d . . . . .
C19 C 0.57513(18) 0.09012(16) 0.73175(14) 0.0232(4) Uani 1 1 d . . . . .
H19 H 0.541466 0.014066 0.734658 0.028 Uiso 1 1 calc R U . . .
C20 C 0.68105(17) 0.13200(16) 0.69734(14) 0.0227(4) Uani 1 1 d . . . . .
H20 H 0.735583 0.090752 0.671398 0.027 Uiso 1 1 calc R U . . .
C21 C 0.89454(17) 0.27647(16) 0.64016(14) 0.0224(4) Uani 1 1 d . . . . .
C22 C 0.8691(2) 0.21689(19) 0.54946(15) 0.0314(5) Uani 1 1 d . . . . .
H22 H 0.790105 0.207181 0.515455 0.038 Uiso 1 1 calc R U . . .
C23 C 0.9578(2) 0.1711(2) 0.50757(17) 0.0411(6) Uani 1 1 d . . . . .
H23 H 0.939165 0.130087 0.445455 0.049 Uiso 1 1 calc R U . . .
C24 C 1.0725(2) 0.1855(2) 0.55641(17) 0.0404(6) Uani 1 1 d . . . . .
H24 H 1.133323 0.154809 0.527673 0.048 Uiso 1 1 calc R U . . .
C25 C 1.0995(2) 0.24402(19) 0.64663(18) 0.0363(5) Uani 1 1 d . . . . .
H25 H 1.178752 0.253468 0.680131 0.044 Uiso 1 1 calc R U . . .
C26 C 1.01050(18) 0.28952(17) 0.68895(15) 0.0263(4) Uani 1 1 d . . . . .
H26 H 1.029225 0.329599 0.751375 0.032 Uiso 1 1 calc R U . . .
C31 C 0.26494(16) 0.59927(15) 0.94256(13) 0.0187(4) Uani 1 1 d . . . . .
C32 C 0.29165(17) 0.67787(16) 1.02478(13) 0.0214(4) Uani 1 1 d . . . . .
H32 H 0.373931 0.702049 1.055380 0.026 Uiso 1 1 calc R U . . .
C33 C 0.19942(18) 0.72121(17) 1.06245(14) 0.0247(4) Uani 1 1 d . . . . .
H33 H 0.219096 0.775548 1.118237 0.030 Uiso 1 1 calc R U . . .
C34 C 0.07844(18) 0.68586(16) 1.01929(14) 0.0249(4) Uani 1 1 d . . . . .
H34 H 0.015390 0.715964 1.045148 0.030 Uiso 1 1 calc R U . . .
C35 C 0.05044(17) 0.60626(16) 0.93816(14) 0.0245(4) Uani 1 1 d . . . . .
H35 H -0.032378 0.580423 0.908790 0.029 Uiso 1 1 calc R U . . .
C36 C 0.14352(17) 0.56428(15) 0.89981(13) 0.0211(4) Uani 1 1 d . . . . .
H36 H 0.123937 0.510813 0.843488 0.025 Uiso 1 1 calc R U . . .
C41 C 0.82840(16) 0.81921(15) 0.78766(13) 0.0195(4) Uani 1 1 d . . . . .
C42 C 0.85202(18) 0.85970(16) 0.70574(14) 0.0238(4) Uani 1 1 d . . . . .
H42 H 0.821271 0.812511 0.646984 0.029 Uiso 1 1 calc R U . . .
C43 C 0.91954(18) 0.96752(17) 0.70854(15) 0.0268(4) Uani 1 1 d . . . . .
H43 H 0.935068 0.993684 0.651890 0.032 Uiso 1 1 calc R U . . .
C44 C 0.96450(19) 1.03735(17) 0.79324(15) 0.0296(5) Uani 1 1 d . . . . .
H44 H 1.011920 1.111116 0.795051 0.036 Uiso 1 1 calc R U . . .
C45 C 0.9401(2) 0.99933(18) 0.87559(16) 0.0344(5) Uani 1 1 d . . . . .
H45 H 0.969116 1.047488 0.934142 0.041 Uiso 1 1 calc R U . . .
C46 C 0.8732(2) 0.89050(17) 0.87229(14) 0.0289(4) Uani 1 1 d . . . . .
H46 H 0.857758 0.864492 0.929020 0.035 Uiso 1 1 calc R U . . .
C51 C 0.34679(17) 0.06215(15) 0.82041(14) 0.0211(4) Uani 1 1 d . . . . .
C52 C 0.3370(2) 0.03452(17) 0.90880(15) 0.0279(4) Uani 1 1 d . . . . .
H52 H 0.379865 0.086517 0.962421 0.034 Uiso 1 1 calc R U . . .
C53 C 0.2661(2) -0.06720(18) 0.91967(16) 0.0329(5) Uani 1 1 d . . . . .
H53 H 0.259096 -0.084032 0.980601 0.039 Uiso 1 1 calc R U . . .
C54 C 0.20517(19) -0.14459(17) 0.84257(17) 0.0337(5) Uani 1 1 d . . . . .
H54 H 0.155542 -0.214313 0.850138 0.040 Uiso 1 1 calc R U . . .
C55 C 0.2170(2) -0.11985(18) 0.75426(17) 0.0343(5) Uani 1 1 d . . . . .
H55 H 0.177324 -0.173801 0.700826 0.041 Uiso 1 1 calc R U . . .
C56 C 0.28629(19) -0.01674(16) 0.74290(15) 0.0277(4) Uani 1 1 d . . . . .
H56 H 0.292399 -0.000039 0.681863 0.033 Uiso 1 1 calc R U . . .
O61 O 0.46636(13) 0.43071(12) 0.64573(10) 0.0312(3) Uani 1 1 d . U . . .
C62 C 0.3856(2) 0.48416(19) 0.64146(16) 0.0346(4) Uani 1 1 d . U . . .
H62 H 0.373865 0.527799 0.697884 0.041 Uiso 1 1 calc R U . . .
N63 N 0.31550(17) 0.48498(17) 0.56532(13) 0.0378(4) Uani 1 1 d . . . . .
C64 C 0.3252(3) 0.4194(3) 0.47825(18) 0.0577(8) Uani 1 1 d . . . . .
H64A H 0.392971 0.382642 0.486298 0.087 Uiso 1 1 calc R U . . .
H64B H 0.341880 0.467591 0.431597 0.087 Uiso 1 1 calc R U . . .
H64C H 0.247573 0.362790 0.457068 0.087 Uiso 1 1 calc R U . . .
C65 C 0.2213(3) 0.5477(3) 0.5658(2) 0.0640(9) Uani 1 1 d . . . . .
H65A H 0.222112 0.587704 0.629285 0.096 Uiso 1 1 calc R U . . .
H65B H 0.139985 0.496376 0.544960 0.096 Uiso 1 1 calc R U . . .
H65C H 0.238049 0.601322 0.523358 0.096 Uiso 1 1 calc R U . . .
C101 C 0.4900(3) 0.1791(2) 0.51178(19) 0.0531(7) Uani 1 1 d . . . . .
H10A H 0.559467 0.150193 0.535690 0.064 Uiso 1 1 calc R U . . .
H10B H 0.488681 0.247608 0.555582 0.064 Uiso 1 1 calc R U . . .
N1 N 0.59773(13) 0.27980(12) 0.74698(10) 0.0178(3) Uani 1 1 d . . . . .
N2 N 0.74473(13) 0.50255(13) 0.74574(11) 0.0185(3) Uani 1 1 d . . . . .
N3 N 0.56351(14) 0.59761(12) 0.83742(11) 0.0184(3) Uani 1 1 d . . . . .
N4 N 0.42256(14) 0.37621(12) 0.84620(11) 0.0183(3) Uani 1 1 d . . . . .
Cl1 Cl 0.35035(6) 0.07889(7) 0.50755(5) 0.05397(18) Uani 1 1 d . . . . .
Cl2 Cl 0.51353(9) 0.21186(6) 0.40038(6) 0.0676(2) Uani 1 1 d . . . . .
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'
Cl Cl 0.1484 0.1585 '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
N1 Zn1 N2 89.81(6) . . ?
N1 Zn1 N4 89.48(6) . . ?
N2 Zn1 N4 164.75(6) . . ?
N1 Zn1 N3 168.17(6) . . ?
N2 Zn1 N3 88.93(6) . . ?
N4 Zn1 N3 88.65(6) . . ?
N1 Zn1 O61 95.17(6) . . ?
N2 Zn1 O61 98.52(6) . . ?
N4 Zn1 O61 96.72(6) . . ?
N3 Zn1 O61 96.66(6) . . ?
N1 C1 C2 125.60(16) . . ?
N1 C1 C20 109.44(15) . . ?
C2 C1 C20 124.83(17) . . ?
C1 C2 C3 125.42(17) . . ?
C1 C2 C21 117.03(16) . . ?
C3 C2 C21 117.53(16) . . ?
N2 C3 C2 125.92(16) . . ?
N2 C3 C4 109.42(16) . . ?
C2 C3 C4 124.66(17) . . ?
C5 C4 C3 107.12(17) . . ?
C5 C4 H4 126.4 . . ?
C3 C4 H4 126.4 . . ?
C4 C5 C6 107.07(17) . . ?
C4 C5 H5 126.5 . . ?
C6 C5 H5 126.5 . . ?
N2 C6 C7 125.53(16) . . ?
N2 C6 C5 109.71(15) . . ?
C7 C6 C5 124.75(17) . . ?
C8 C7 C6 125.03(17) . . ?
C8 C7 C41 116.71(16) . . ?
C6 C7 C41 118.25(15) . . ?
N3 C8 C7 126.03(16) . . ?
N3 C8 C9 109.47(15) . . ?
C7 C8 C9 124.49(16) . . ?
C10 C9 C8 107.23(16) . . ?
C10 C9 H9 126.4 . . ?
C8 C9 H9 126.4 . . ?
C9 C10 C11 107.03(16) . . ?
C9 C10 H10 126.5 . . ?
C11 C10 H10 126.5 . . ?
N3 C11 C12 125.24(16) . . ?
N3 C11 C10 109.59(15) . . ?
C12 C11 C10 125.17(16) . . ?
C11 C12 C13 124.99(16) . . ?
C11 C12 C31 118.02(16) . . ?
C13 C12 C31 116.99(15) . . ?
N4 C13 C12 125.90(16) . . ?
N4 C13 C14 109.63(16) . . ?
C12 C13 C14 124.46(16) . . ?
C15 C14 C13 107.15(16) . . ?
C15 C14 H14 126.4 . . ?
C13 C14 H14 126.4 . . ?
C14 C15 C16 107.02(16) . . ?
C14 C15 H15 126.5 . . ?
C16 C15 H15 126.5 . . ?
N4 C16 C17 125.58(16) . . ?
N4 C16 C15 109.54(15) . . ?
C17 C16 C15 124.88(17) . . ?
C18 C17 C16 125.41(17) . . ?
C18 C17 C51 117.95(16) . . ?
C16 C17 C51 116.60(15) . . ?
N1 C18 C17 125.74(16) . . ?
N1 C18 C19 109.36(15) . . ?
C17 C18 C19 124.74(17) . . ?
C20 C19 C18 107.08(17) . . ?
C20 C19 H19 126.5 . . ?
C18 C19 H19 126.5 . . ?
C19 C20 C1 107.29(16) . . ?
C19 C20 H20 126.4 . . ?
C1 C20 H20 126.4 . . ?
C22 C21 C26 118.78(18) . . ?
C22 C21 C2 120.93(18) . . ?
C26 C21 C2 120.30(18) . . ?
C21 C22 C23 120.8(2) . . ?
C21 C22 H22 119.6 . . ?
C23 C22 H22 119.6 . . ?
C24 C23 C22 119.8(2) . . ?
C24 C23 H23 120.1 . . ?
C22 C23 H23 120.1 . . ?
C25 C24 C23 120.3(2) . . ?
C25 C24 H24 119.8 . . ?
C23 C24 H24 119.8 . . ?
C24 C25 C26 120.0(2) . . ?
C24 C25 H25 120.0 . . ?
C26 C25 H25 120.0 . . ?
C21 C26 C25 120.3(2) . . ?
C21 C26 H26 119.8 . . ?
C25 C26 H26 119.8 . . ?
C36 C31 C32 118.55(17) . . ?
C36 C31 C12 120.69(17) . . ?
C32 C31 C12 120.76(17) . . ?
C33 C32 C31 120.60(18) . . ?
C33 C32 H32 119.7 . . ?
C31 C32 H32 119.7 . . ?
C32 C33 C34 120.48(19) . . ?
C32 C33 H33 119.8 . . ?
C34 C33 H33 119.8 . . ?
C35 C34 C33 119.40(17) . . ?
C35 C34 H34 120.3 . . ?
C33 C34 H34 120.3 . . ?
C34 C35 C36 119.94(18) . . ?
C34 C35 H35 120.0 . . ?
C36 C35 H35 120.0 . . ?
C35 C36 C31 121.02(18) . . ?
C35 C36 H36 119.5 . . ?
C31 C36 H36 119.5 . . ?
C46 C41 C42 118.15(18) . . ?
C46 C41 C7 119.81(17) . . ?
C42 C41 C7 122.01(17) . . ?
C43 C42 C41 120.99(19) . . ?
C43 C42 H42 119.5 . . ?
C41 C42 H42 119.5 . . ?
C44 C43 C42 120.29(18) . . ?
C44 C43 H43 119.9 . . ?
C42 C43 H43 119.9 . . ?
C43 C44 C45 119.63(19) . . ?
C43 C44 H44 120.2 . . ?
C45 C44 H44 120.2 . . ?
C44 C45 C46 119.8(2) . . ?
C44 C45 H45 120.1 . . ?
C46 C45 H45 120.1 . . ?
C41 C46 C45 121.15(19) . . ?
C41 C46 H46 119.4 . . ?
C45 C46 H46 119.4 . . ?
C56 C51 C52 118.36(18) . . ?
C56 C51 C17 120.92(17) . . ?
C52 C51 C17 120.69(18) . . ?
C53 C52 C51 121.0(2) . . ?
C53 C52 H52 119.5 . . ?
C51 C52 H52 119.5 . . ?
C54 C53 C52 120.3(2) . . ?
C54 C53 H53 119.8 . . ?
C52 C53 H53 119.8 . . ?
C53 C54 C55 119.41(19) . . ?
C53 C54 H54 120.3 . . ?
C55 C54 H54 120.3 . . ?
C54 C55 C56 120.5(2) . . ?
C54 C55 H55 119.7 . . ?
C56 C55 H55 119.7 . . ?
C55 C56 C51 120.3(2) . . ?
C55 C56 H56 119.8 . . ?
C51 C56 H56 119.8 . . ?
C62 O61 Zn1 119.73(14) . . ?
O61 C62 N63 125.1(2) . . ?
O61 C62 H62 117.4 . . ?
N63 C62 H62 117.4 . . ?
C62 N63 C64 120.8(2) . . ?
C62 N63 C65 122.2(2) . . ?
C64 N63 C65 116.9(2) . . ?
N63 C64 H64A 109.5 . . ?
N63 C64 H64B 109.5 . . ?
H64A C64 H64B 109.5 . . ?
N63 C64 H64C 109.5 . . ?
H64A C64 H64C 109.5 . . ?
H64B C64 H64C 109.5 . . ?
N63 C65 H65A 109.5 . . ?
N63 C65 H65B 109.5 . . ?
H65A C65 H65B 109.5 . . ?
N63 C65 H65C 109.5 . . ?
H65A C65 H65C 109.5 . . ?
H65B C65 H65C 109.5 . . ?
Cl1 C101 Cl2 111.35(15) . . ?
Cl1 C101 H10A 109.4 . . ?
Cl2 C101 H10A 109.4 . . ?
Cl1 C101 H10B 109.4 . . ?
Cl2 C101 H10B 109.4 . . ?
H10A C101 H10B 108.0 . . ?
C18 N1 C1 106.82(14) . . ?
C18 N1 Zn1 126.70(12) . . ?
C1 N1 Zn1 126.46(12) . . ?
C6 N2 C3 106.67(14) . . ?
C6 N2 Zn1 126.93(12) . . ?
C3 N2 Zn1 126.08(12) . . ?
C8 N3 C11 106.64(14) . . ?
C8 N3 Zn1 125.31(12) . . ?
C11 N3 Zn1 125.76(12) . . ?
C16 N4 C13 106.64(14) . . ?
C16 N4 Zn1 126.71(12) . . ?
C13 N4 Zn1 126.56(12) . . ?
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 N1 2.0543(15) . ?
Zn1 N2 2.0560(15) . ?
Zn1 N4 2.0614(15) . ?
Zn1 N3 2.0726(15) . ?
Zn1 O61 2.1609(14) . ?
C1 N1 1.375(2) . ?
C1 C2 1.403(3) . ?
C1 C20 1.443(3) . ?
C2 C3 1.405(3) . ?
C2 C21 1.502(2) . ?
C3 N2 1.373(2) . ?
C3 C4 1.443(2) . ?
C4 C5 1.354(3) . ?
C4 H4 0.9500 . ?
C5 C6 1.439(2) . ?
C5 H5 0.9500 . ?
C6 N2 1.371(2) . ?
C6 C7 1.408(3) . ?
C7 C8 1.400(2) . ?
C7 C41 1.499(2) . ?
C8 N3 1.371(2) . ?
C8 C9 1.444(3) . ?
C9 C10 1.350(3) . ?
C9 H9 0.9500 . ?
C10 C11 1.443(3) . ?
C10 H10 0.9500 . ?
C11 N3 1.372(2) . ?
C11 C12 1.406(2) . ?
C12 C13 1.406(3) . ?
C12 C31 1.498(2) . ?
C13 N4 1.372(2) . ?
C13 C14 1.440(2) . ?
C14 C15 1.352(3) . ?
C14 H14 0.9500 . ?
C15 C16 1.444(2) . ?
C15 H15 0.9500 . ?
C16 N4 1.371(2) . ?
C16 C17 1.408(3) . ?
C17 C18 1.401(2) . ?
C17 C51 1.497(2) . ?
C18 N1 1.374(2) . ?
C18 C19 1.448(3) . ?
C19 C20 1.353(3) . ?
C19 H19 0.9500 . ?
C20 H20 0.9500 . ?
C21 C22 1.386(3) . ?
C21 C26 1.390(3) . ?
C22 C23 1.391(3) . ?
C22 H22 0.9500 . ?
C23 C24 1.376(4) . ?
C23 H23 0.9500 . ?
C24 C25 1.375(4) . ?
C24 H24 0.9500 . ?
C25 C26 1.395(3) . ?
C25 H25 0.9500 . ?
C26 H26 0.9500 . ?
C31 C36 1.390(3) . ?
C31 C32 1.391(3) . ?
C32 C33 1.384(3) . ?
C32 H32 0.9500 . ?
C33 C34 1.388(3) . ?
C33 H33 0.9500 . ?
C34 C35 1.385(3) . ?
C34 H34 0.9500 . ?
C35 C36 1.388(3) . ?
C35 H35 0.9500 . ?
C36 H36 0.9500 . ?
C41 C46 1.386(3) . ?
C41 C42 1.391(3) . ?
C42 C43 1.382(3) . ?
C42 H42 0.9500 . ?
C43 C44 1.380(3) . ?
C43 H43 0.9500 . ?
C44 C45 1.384(3) . ?
C44 H44 0.9500 . ?
C45 C46 1.389(3) . ?
C45 H45 0.9500 . ?
C46 H46 0.9500 . ?
C51 C56 1.390(3) . ?
C51 C52 1.392(3) . ?
C52 C53 1.379(3) . ?
C52 H52 0.9500 . ?
C53 C54 1.379(3) . ?
C53 H53 0.9500 . ?
C54 C55 1.381(3) . ?
C54 H54 0.9500 . ?
C55 C56 1.389(3) . ?
C55 H55 0.9500 . ?
C56 H56 0.9500 . ?
O61 C62 1.244(3) . ?
C62 N63 1.308(3) . ?
C62 H62 0.9500 . ?
N63 C64 1.427(3) . ?
N63 C65 1.451(3) . ?
C64 H64A 0.9800 . ?
C64 H64B 0.9800 . ?
C64 H64C 0.9800 . ?
C65 H65A 0.9800 . ?
C65 H65B 0.9800 . ?
C65 H65C 0.9800 . ?
C101 Cl1 1.757(3) . ?
C101 Cl2 1.763(3) . ?
C101 H10A 0.9900 . ?
C101 H10B 0.9900 . ?
loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
N1 C1 C2 C3 3.0(3) . . . . ?
C20 C1 C2 C3 -172.48(18) . . . . ?
N1 C1 C2 C21 -178.45(17) . . . . ?
C20 C1 C2 C21 6.1(3) . . . . ?
C1 C2 C3 N2 -1.3(3) . . . . ?
C21 C2 C3 N2 -179.92(17) . . . . ?
C1 C2 C3 C4 178.47(18) . . . . ?
C21 C2 C3 C4 -0.1(3) . . . . ?
N2 C3 C4 C5 0.6(2) . . . . ?
C2 C3 C4 C5 -179.26(18) . . . . ?
C3 C4 C5 C6 -1.0(2) . . . . ?
C4 C5 C6 N2 1.1(2) . . . . ?
C4 C5 C6 C7 -177.84(18) . . . . ?
N2 C6 C7 C8 0.8(3) . . . . ?
C5 C6 C7 C8 179.57(18) . . . . ?
N2 C6 C7 C41 179.53(17) . . . . ?
C5 C6 C7 C41 -1.7(3) . . . . ?
C6 C7 C8 N3 6.0(3) . . . . ?
C41 C7 C8 N3 -172.66(17) . . . . ?
C6 C7 C8 C9 -172.79(18) . . . . ?
C41 C7 C8 C9 8.5(3) . . . . ?
N3 C8 C9 C10 0.8(2) . . . . ?
C7 C8 C9 C10 179.77(18) . . . . ?
C8 C9 C10 C11 0.4(2) . . . . ?
C9 C10 C11 N3 -1.4(2) . . . . ?
C9 C10 C11 C12 179.30(18) . . . . ?
N3 C11 C12 C13 -2.0(3) . . . . ?
C10 C11 C12 C13 177.23(18) . . . . ?
N3 C11 C12 C31 178.81(16) . . . . ?
C10 C11 C12 C31 -2.0(3) . . . . ?
C11 C12 C13 N4 -7.3(3) . . . . ?
C31 C12 C13 N4 171.94(17) . . . . ?
C11 C12 C13 C14 174.04(18) . . . . ?
C31 C12 C13 C14 -6.7(3) . . . . ?
N4 C13 C14 C15 -1.5(2) . . . . ?
C12 C13 C14 C15 177.37(18) . . . . ?
C13 C14 C15 C16 0.8(2) . . . . ?
C14 C15 C16 N4 0.1(2) . . . . ?
C14 C15 C16 C17 -179.30(18) . . . . ?
N4 C16 C17 C18 3.5(3) . . . . ?
C15 C16 C17 C18 -177.11(18) . . . . ?
N4 C16 C17 C51 -178.74(17) . . . . ?
C15 C16 C17 C51 0.6(3) . . . . ?
C16 C17 C18 N1 -2.5(3) . . . . ?
C51 C17 C18 N1 179.83(17) . . . . ?
C16 C17 C18 C19 172.45(18) . . . . ?
C51 C17 C18 C19 -5.3(3) . . . . ?
N1 C18 C19 C20 0.3(2) . . . . ?
C17 C18 C19 C20 -175.32(18) . . . . ?
C18 C19 C20 C1 0.2(2) . . . . ?
N1 C1 C20 C19 -0.6(2) . . . . ?
C2 C1 C20 C19 175.46(18) . . . . ?
C1 C2 C21 C22 69.1(2) . . . . ?
C3 C2 C21 C22 -112.2(2) . . . . ?
C1 C2 C21 C26 -110.6(2) . . . . ?
C3 C2 C21 C26 68.1(2) . . . . ?
C26 C21 C22 C23 -0.2(3) . . . . ?
C2 C21 C22 C23 -179.9(2) . . . . ?
C21 C22 C23 C24 -0.3(4) . . . . ?
C22 C23 C24 C25 0.5(4) . . . . ?
C23 C24 C25 C26 -0.2(3) . . . . ?
C22 C21 C26 C25 0.5(3) . . . . ?
C2 C21 C26 C25 -179.80(18) . . . . ?
C24 C25 C26 C21 -0.3(3) . . . . ?
C11 C12 C31 C36 119.7(2) . . . . ?
C13 C12 C31 C36 -59.6(2) . . . . ?
C11 C12 C31 C32 -60.9(2) . . . . ?
C13 C12 C31 C32 119.77(19) . . . . ?
C36 C31 C32 C33 -0.8(3) . . . . ?
C12 C31 C32 C33 179.80(17) . . . . ?
C31 C32 C33 C34 0.8(3) . . . . ?
C32 C33 C34 C35 0.3(3) . . . . ?
C33 C34 C35 C36 -1.3(3) . . . . ?
C34 C35 C36 C31 1.2(3) . . . . ?
C32 C31 C36 C35 -0.2(3) . . . . ?
C12 C31 C36 C35 179.18(17) . . . . ?
C8 C7 C41 C46 63.3(2) . . . . ?
C6 C7 C41 C46 -115.5(2) . . . . ?
C8 C7 C41 C42 -114.4(2) . . . . ?
C6 C7 C41 C42 66.8(2) . . . . ?
C46 C41 C42 C43 0.8(3) . . . . ?
C7 C41 C42 C43 178.59(17) . . . . ?
C41 C42 C43 C44 -0.3(3) . . . . ?
C42 C43 C44 C45 -0.9(3) . . . . ?
C43 C44 C45 C46 1.5(3) . . . . ?
C42 C41 C46 C45 -0.2(3) . . . . ?
C7 C41 C46 C45 -178.04(19) . . . . ?
C44 C45 C46 C41 -0.9(3) . . . . ?
C18 C17 C51 C56 -65.9(2) . . . . ?
C16 C17 C51 C56 116.2(2) . . . . ?
C18 C17 C51 C52 116.3(2) . . . . ?
C16 C17 C51 C52 -61.6(2) . . . . ?
C56 C51 C52 C53 -2.0(3) . . . . ?
C17 C51 C52 C53 175.88(18) . . . . ?
C51 C52 C53 C54 1.3(3) . . . . ?
C52 C53 C54 C55 0.7(3) . . . . ?
C53 C54 C55 C56 -2.0(3) . . . . ?
C54 C55 C56 C51 1.3(3) . . . . ?
C52 C51 C56 C55 0.7(3) . . . . ?
C17 C51 C56 C55 -177.15(18) . . . . ?
Zn1 O61 C62 N63 -179.00(18) . . . . ?
O61 C62 N63 C64 1.6(4) . . . . ?
O61 C62 N63 C65 178.8(2) . . . . ?
C17 C18 N1 C1 174.89(17) . . . . ?
C19 C18 N1 C1 -0.7(2) . . . . ?
C17 C18 N1 Zn1 -3.6(3) . . . . ?
C19 C18 N1 Zn1 -179.21(12) . . . . ?
C2 C1 N1 C18 -175.24(18) . . . . ?
C20 C1 N1 C18 0.8(2) . . . . ?
C2 C1 N1 Zn1 3.3(3) . . . . ?
C20 C1 N1 Zn1 179.33(12) . . . . ?
C7 C6 N2 C3 178.21(17) . . . . ?
C5 C6 N2 C3 -0.7(2) . . . . ?
C7 C6 N2 Zn1 4.5(3) . . . . ?
C5 C6 N2 Zn1 -174.42(12) . . . . ?
C2 C3 N2 C6 179.92(17) . . . . ?
C4 C3 N2 C6 0.1(2) . . . . ?
C2 C3 N2 Zn1 -6.3(3) . . . . ?
C4 C3 N2 Zn1 173.88(12) . . . . ?
C7 C8 N3 C11 179.40(17) . . . . ?
C9 C8 N3 C11 -1.6(2) . . . . ?
C7 C8 N3 Zn1 -17.0(3) . . . . ?
C9 C8 N3 Zn1 161.96(12) . . . . ?
C12 C11 N3 C8 -178.84(17) . . . . ?
C10 C11 N3 C8 1.9(2) . . . . ?
C12 C11 N3 Zn1 17.7(3) . . . . ?
C10 C11 N3 Zn1 -161.63(12) . . . . ?
C17 C16 N4 C13 178.38(18) . . . . ?
C15 C16 N4 C13 -1.1(2) . . . . ?
C17 C16 N4 Zn1 1.6(3) . . . . ?
C15 C16 N4 Zn1 -177.80(12) . . . . ?
C12 C13 N4 C16 -177.28(18) . . . . ?
C14 C13 N4 C16 1.5(2) . . . . ?
C12 C13 N4 Zn1 -0.5(3) . . . . ?
C14 C13 N4 Zn1 178.30(12) . . . . ?
