# Electronic Supplementary Material (ESI) for RSC Advances.
# This journal is © The Royal Society of Chemistry 2023

####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_eg_bangam

_database_code_depnum_ccdc_archive 'CCDC 2269252'
loop_
_audit_author_name
_audit_author_address
'Christoph Wolper'
;Universitaet Duisburg Essen
Germany
;
_audit_update_record             
;
2023-06-12 deposited with the CCDC.	2023-10-05 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2017/1
_shelx_SHELXL_version_number     2017/1
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C27 H42 N4 O Zn2'
_chemical_formula_weight         569.38

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'

_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'

_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.
;

loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   7.9884(6)
_cell_length_b                   8.0941(7)
_cell_length_c                   22.3164(18)
_cell_angle_alpha                98.388(4)
_cell_angle_beta                 95.725(4)
_cell_angle_gamma                106.622(4)
_cell_volume                     1352.54(19)
_cell_formula_units_Z            2
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    9804
_cell_measurement_theta_min      2.66
_cell_measurement_theta_max      31.24

_exptl_crystal_description       tablet
_exptl_crystal_colour            'pale yellow'
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.398
_exptl_crystal_F_000             600
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.255
_exptl_crystal_size_mid          0.119
_exptl_crystal_size_min          0.050
_exptl_absorpt_coefficient_mu    1.799
_shelx_estimated_absorpt_T_min   0.657
_shelx_estimated_absorpt_T_max   0.915
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.64
_exptl_absorpt_correction_T_max  0.75
_exptl_absorpt_process_details   
; 
 SADABS
 R.H. Blessing, Acta Cryst. (1995) A51 33-38 
;
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  'Triumph Goebel mirror'
_diffrn_measurement_device_type  'Bruker D8 KAPPA II (APEX II detector)'
_diffrn_measurement_method       'Data collection strategy APEX 3/QUEEN'
_diffrn_detector_area_resol_mean 512
_diffrn_reflns_number            92625
_diffrn_reflns_av_unetI/netI     0.0261
_diffrn_reflns_av_R_equivalents  0.0446
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_l_min       -34
_diffrn_reflns_limit_l_max       34
_diffrn_reflns_theta_min         2.664
_diffrn_reflns_theta_max         33.268
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.994
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.994
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.994
_diffrn_reflns_point_group_measured_fraction_full 1.000
_reflns_number_total             10387
_reflns_number_gt                8666
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.

 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_computing_data_collection       'BRUKER APEX3(v2019.1-0)'
_computing_cell_refinement       'BRUKER APEX3(v2019.1-0)'
_computing_data_reduction        'BRUKER APEX3(v2019.1-0)'
_computing_structure_solution    'BRUKER APEX3(v2019.1-0)'
_computing_structure_refinement  'SHELXL-2017/1 (Sheldrick, 2017)'
_computing_molecular_graphics    'ORTEP/PLATON (Spek)'
_computing_publication_material  'BRUKER AXS SHELXTL (c) 2008 / Vers. 2008/4'

_refine_special_details          
;
 Treatment of hydrogen atoms:    
 Riding model on idealized geometries 
 with the 1.2 fold isotropic displacement 
 parameters of the equivalent Uij of the 
 corresponding carbon atom.
 The methyl groups are idealized with
 tetrahedral angles in a combined 
 rotating and rigid group refinement
 with the 1.5 fold isotropic displacement
 parameters of the equivalent Uij of the 
 corresponding carbon atom.
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0322P)²+0.5120P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   diffmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         10387
_refine_ls_number_parameters     313
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0406
_refine_ls_R_factor_gt           0.0290
_refine_ls_wR_factor_ref         0.0679
_refine_ls_wR_factor_gt          0.0640
_refine_ls_goodness_of_fit_ref   1.040
_refine_ls_restrained_S_all      1.040
_refine_ls_shift/su_max          0.003
_refine_ls_shift/su_mean         0.000

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 0.67166(2) 0.42020(2) 0.82461(2) 0.01123(3) Uani 1 1 d . . . . .
Zn2 Zn 0.50235(2) 0.31990(2) 0.66751(2) 0.01247(4) Uani 1 1 d . . . . .
O1 O 0.48356(11) 0.27287(11) 0.75418(4) 0.01236(15) Uani 1 1 d . . . . .
N1 N 0.57054(14) 0.32373(14) 0.89222(5) 0.01456(19) Uani 1 1 d . . . . .
N2 N 0.29279(14) 0.13465(15) 0.62519(5) 0.0169(2) Uani 1 1 d . . . . .
N3 N 0.88338(14) 0.31062(14) 0.83507(5) 0.01406(18) Uani 1 1 d . . . . .
N4 N 0.38982(14) 0.52344(15) 0.64929(5) 0.0160(2) Uani 1 1 d . . . . .
C1 C 0.42526(16) 0.18880(16) 0.88261(6) 0.0144(2) Uani 1 1 d . . . . .
C2 C 0.32548(16) 0.10943(16) 0.82473(6) 0.0149(2) Uani 1 1 d . . . . .
H2 H 0.221175 0.017860 0.826060 0.018 Uiso 1 1 calc R U . . .
C3 C 0.35026(15) 0.13948(15) 0.76480(5) 0.0120(2) Uani 1 1 d . . . . .
C4 C 0.22440(16) 0.02187(16) 0.71673(6) 0.0150(2) Uani 1 1 d . . . . .
H4 H 0.146334 -0.074364 0.729664 0.018 Uiso 1 1 calc R U . . .
C5 C 0.19319(16) 0.02057(16) 0.65360(6) 0.0144(2) Uani 1 1 d . . . . .
C6 C 0.35550(19) 0.1100(2) 0.93621(6) 0.0222(3) Uani 1 1 d . . . . .
H6A H 0.241271 0.019884 0.921826 0.033 Uiso 1 1 calc R U . . .
H6B H 0.340667 0.202242 0.967000 0.033 Uiso 1 1 calc R U . . .
H6C H 0.439482 0.057070 0.954446 0.033 Uiso 1 1 calc R U . . .
C7 C 0.03307(18) -0.12292(18) 0.61813(7) 0.0206(3) Uani 1 1 d . . . . .
H7A H -0.053086 -0.070298 0.601213 0.031 Uiso 1 1 calc R U . . .
H7B H -0.020578 -0.200197 0.645564 0.031 Uiso 1 1 calc R U . . .
H7C H 0.069209 -0.191146 0.584653 0.031 Uiso 1 1 calc R U . . .
C8 C 0.69026(18) 0.37431(17) 0.95048(6) 0.0171(2) Uani 1 1 d . . . . .
H8A H 0.623550 0.336061 0.983678 0.020 Uiso 1 1 calc R U . . .
H8AB H 0.741616 0.503533 0.960346 0.020 Uiso 1 1 calc R U . . .
C9 C 0.83866(18) 0.28989(17) 0.94641(6) 0.0180(2) Uani 1 1 d . . . . .
H9A H 0.909143 0.314666 0.987589 0.022 Uiso 1 1 calc R U . . .
H9AB H 0.784662 0.161187 0.934887 0.022 Uiso 1 1 calc R U . . .
C10 C 0.96375(17) 0.35080(18) 0.90094(6) 0.0178(2) Uani 1 1 d . . . . .
H10A H 1.018517 0.479322 0.912881 0.021 Uiso 1 1 calc R U . . .
H10B H 1.059715 0.296431 0.904951 0.021 Uiso 1 1 calc R U . . .
C11 C 1.02523(17) 0.38006(18) 0.79933(6) 0.0188(2) Uani 1 1 d . . . . .
H11A H 0.976876 0.352864 0.755678 0.028 Uiso 1 1 calc R U . . .
H11B H 1.118988 0.325920 0.806103 0.028 Uiso 1 1 calc R U . . .
H11C H 1.073919 0.507468 0.812506 0.028 Uiso 1 1 calc R U . . .
C12 C 0.8092(2) 0.11823(17) 0.81383(6) 0.0196(2) Uani 1 1 d . . . . .
H12A H 0.763159 0.093462 0.770011 0.029 Uiso 1 1 calc R U . . .
H12B H 0.713279 0.071019 0.836679 0.029 Uiso 1 1 calc R U . . .
H12C H 0.902110 0.063143 0.820759 0.029 Uiso 1 1 calc R U . . .
C13 C 0.23881(18) 0.1474(2) 0.56188(6) 0.0218(3) Uani 1 1 d . . . . .
H13A H 0.142776 0.039872 0.542016 0.026 Uiso 1 1 calc R U . . .
H13B H 0.339976 0.156557 0.538937 0.026 Uiso 1 1 calc R U . . .
C14 C 0.17485(18) 0.3071(2) 0.55955(6) 0.0239(3) Uani 1 1 d . . . . .
H14A H 0.126473 0.303428 0.516594 0.029 Uiso 1 1 calc R U . . .
H14B H 0.076776 0.298094 0.583966 0.029 Uiso 1 1 calc R U . . .
C15 C 0.31415(18) 0.4843(2) 0.58293(6) 0.0218(3) Uani 1 1 d . . . . .
H15A H 0.412504 0.492255 0.558690 0.026 Uiso 1 1 calc R U . . .
H15B H 0.261415 0.577018 0.574709 0.026 Uiso 1 1 calc R U . . .
C16 C 0.51608(19) 0.70249(18) 0.66262(7) 0.0216(3) Uani 1 1 d . . . . .
H16A H 0.611343 0.707494 0.637805 0.032 Uiso 1 1 calc R U . . .
H16B H 0.566000 0.732536 0.706157 0.032 Uiso 1 1 calc R U . . .
H16C H 0.454632 0.786158 0.652742 0.032 Uiso 1 1 calc R U . . .
C17 C 0.24738(18) 0.5179(2) 0.68705(7) 0.0222(3) Uani 1 1 d . . . . .
H17A H 0.184017 0.599202 0.676181 0.033 Uiso 1 1 calc R U . . .
H17B H 0.298558 0.552264 0.730464 0.033 Uiso 1 1 calc R U . . .
H17C H 0.165029 0.398651 0.679574 0.033 Uiso 1 1 calc R U . . .
C18 C 0.76120(18) 0.68315(16) 0.81467(6) 0.0174(2) Uani 1 1 d . . . . .
H18 H 0.786191 0.709964 0.773523 0.021 Uiso 1 1 calc R U . . .
C19 C 0.90129(18) 0.75216(16) 0.86605(7) 0.0191(2) Uani 1 1 d . . . . .
H19 H 1.021235 0.756686 0.865404 0.023 Uiso 1 1 calc R U . . .
C20 C 0.8322(2) 0.81056(17) 0.91634(6) 0.0205(3) Uani 1 1 d . . . . .
H20 H 0.896103 0.859788 0.956255 0.025 Uiso 1 1 calc R U . . .
C21 C 0.6499(2) 0.78482(17) 0.89847(6) 0.0207(3) Uani 1 1 d . . . . .
H21 H 0.570890 0.812470 0.924532 0.025 Uiso 1 1 calc R U . . .
C22 C 0.60631(19) 0.71289(17) 0.83688(6) 0.0191(2) Uani 1 1 d . . . . .
H22 H 0.493521 0.687206 0.813071 0.023 Uiso 1 1 calc R U . . .
C23 C 0.75995(16) 0.37204(17) 0.64514(6) 0.0163(2) Uani 1 1 d . . . . .
H23 H 0.858942 0.459775 0.674565 0.020 Uiso 1 1 calc R U . . .
C24 C 0.73313(17) 0.39900(18) 0.58282(6) 0.0181(2) Uani 1 1 d . . . . .
H24 H 0.741031 0.508359 0.570672 0.022 Uiso 1 1 calc R U . . .
C25 C 0.69415(18) 0.23992(19) 0.54380(6) 0.0193(2) Uani 1 1 d . . . . .
H25 H 0.667763 0.221083 0.500426 0.023 Uiso 1 1 calc R U . . .
C26 C 0.70000(18) 0.10934(18) 0.57915(6) 0.0192(2) Uani 1 1 d . . . . .
H26 H 0.676503 -0.011940 0.563479 0.023 Uiso 1 1 calc R U . . .
C27 C 0.74563(17) 0.18779(18) 0.64030(6) 0.0181(2) Uani 1 1 d . . . . .
H27 H 0.764401 0.130628 0.673488 0.022 Uiso 1 1 calc R U . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;

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 1.9402(11) . ?
Zn1 O1 2.0266(9) . ?
Zn1 C18 2.0950(13) . ?
Zn1 N3 2.1311(11) . ?
Zn1 C22 2.5508(13) . ?
Zn2 N2 1.9437(11) . ?
Zn2 O1 2.0367(9) . ?
Zn2 C23 2.1051(12) . ?
Zn2 N4 2.1582(11) . ?
Zn2 C27 2.5542(13) . ?
O1 C3 1.3502(14) . ?
N1 C1 1.3200(16) . ?
N1 C8 1.4647(16) . ?
N2 C5 1.3187(17) . ?
N2 C13 1.4627(17) . ?
N3 C11 1.4774(17) . ?
N3 C12 1.4838(17) . ?
N3 C10 1.4939(16) . ?
N4 C17 1.4766(17) . ?
N4 C16 1.4779(18) . ?
N4 C15 1.4945(17) . ?
C1 C2 1.4056(18) . ?
C1 C6 1.5167(18) . ?
C2 C3 1.4168(17) . ?
C3 C4 1.4168(17) . ?
C4 C5 1.4039(18) . ?
C5 C7 1.5137(17) . ?
C8 C9 1.5321(19) . ?
C9 C10 1.5289(19) . ?
C13 C14 1.526(2) . ?
C14 C15 1.523(2) . ?
C18 C19 1.4417(19) . ?
C18 C22 1.447(2) . ?
C19 C20 1.381(2) . ?
C20 C21 1.418(2) . ?
C21 C22 1.3798(19) . ?
C23 C24 1.4434(18) . ?
C23 C27 1.4498(19) . ?
C24 C25 1.379(2) . ?
C25 C26 1.416(2) . ?
C26 C27 1.3834(19) . ?

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 O1 99.59(4) . . ?
N1 Zn1 C18 128.71(5) . . ?
O1 Zn1 C18 111.80(4) . . ?
N1 Zn1 N3 92.25(4) . . ?
O1 Zn1 N3 110.57(4) . . ?
C18 Zn1 N3 111.80(5) . . ?
N1 Zn1 C22 101.35(5) . . ?
O1 Zn1 C22 102.07(4) . . ?
C18 Zn1 C22 34.55(5) . . ?
N3 Zn1 C22 141.90(4) . . ?
N2 Zn2 O1 98.30(4) . . ?
N2 Zn2 C23 126.99(5) . . ?
O1 Zn2 C23 114.01(4) . . ?
N2 Zn2 N4 92.63(5) . . ?
O1 Zn2 N4 111.71(4) . . ?
C23 Zn2 N4 111.01(5) . . ?
N2 Zn2 C27 101.07(5) . . ?
O1 Zn2 C27 101.19(4) . . ?
C23 Zn2 C27 34.58(5) . . ?
N4 Zn2 C27 142.03(4) . . ?
C3 O1 Zn1 119.56(7) . . ?
C3 O1 Zn2 120.46(7) . . ?
Zn1 O1 Zn2 119.94(4) . . ?
C1 N1 C8 121.50(11) . . ?
C1 N1 Zn1 121.24(9) . . ?
C8 N1 Zn1 114.90(8) . . ?
C5 N2 C13 122.04(11) . . ?
C5 N2 Zn2 122.49(9) . . ?
C13 N2 Zn2 114.84(9) . . ?
C11 N3 C12 108.75(10) . . ?
C11 N3 C10 107.63(10) . . ?
C12 N3 C10 110.30(10) . . ?
C11 N3 Zn1 113.06(8) . . ?
C12 N3 Zn1 107.61(8) . . ?
C10 N3 Zn1 109.49(8) . . ?
C17 N4 C16 108.83(11) . . ?
C17 N4 C15 109.73(10) . . ?
C16 N4 C15 107.76(11) . . ?
C17 N4 Zn2 107.45(8) . . ?
C16 N4 Zn2 114.83(8) . . ?
C15 N4 Zn2 108.19(8) . . ?
N1 C1 C2 124.43(11) . . ?
N1 C1 C6 119.90(11) . . ?
C2 C1 C6 115.68(11) . . ?
C1 C2 C3 132.48(12) . . ?
O1 C3 C2 122.26(11) . . ?
O1 C3 C4 122.13(11) . . ?
C2 C3 C4 115.60(11) . . ?
C5 C4 C3 132.19(12) . . ?
N2 C5 C4 124.11(11) . . ?
N2 C5 C7 120.23(12) . . ?
C4 C5 C7 115.66(12) . . ?
N1 C8 C9 110.18(10) . . ?
C10 C9 C8 115.34(11) . . ?
N3 C10 C9 116.31(11) . . ?
N2 C13 C14 110.87(11) . . ?
C15 C14 C13 115.52(11) . . ?
N4 C15 C14 116.66(11) . . ?
C19 C18 C22 105.45(11) . . ?
C19 C18 Zn1 100.38(8) . . ?
C22 C18 Zn1 90.24(8) . . ?
C20 C19 C18 108.67(12) . . ?
C19 C20 C21 108.62(12) . . ?
C22 C21 C20 108.59(12) . . ?
C21 C22 C18 108.55(12) . . ?
C21 C22 Zn1 106.32(9) . . ?
C18 C22 Zn1 55.22(7) . . ?
C24 C23 C27 105.31(11) . . ?
C24 C23 Zn2 101.76(8) . . ?
C27 C23 Zn2 89.91(8) . . ?
C25 C24 C23 108.81(12) . . ?
C24 C25 C26 108.66(12) . . ?
C27 C26 C25 108.65(12) . . ?
C26 C27 C23 108.40(12) . . ?
C26 C27 Zn2 106.68(9) . . ?
C23 C27 Zn2 55.50(6) . . ?

_refine_diff_density_max         0.714
_refine_diff_density_min         -0.625
_refine_diff_density_rms         0.073

####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_eg_l3hzncp2_tw5

_database_code_depnum_ccdc_archive 'CCDC 2269253'
loop_
_audit_author_name
_audit_author_address
'Christoph Wolper'
;Universitaet Duisburg Essen
Germany
;
_audit_update_record             
;
2023-06-12 deposited with the CCDC.	2023-10-05 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2017/1
_shelx_SHELXL_version_number     2017/1
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C27 H48 N4 O Zn'
_chemical_formula_weight         510.06

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 '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 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Zn Zn -1.5491 0.6778 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'

_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.
;

loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   8.0513(4)
_cell_length_b                   12.3749(6)
_cell_length_c                   14.7581(7)
_cell_angle_alpha                81.3299(17)
_cell_angle_beta                 81.6550(17)
_cell_angle_gamma                74.9858(17)
_cell_volume                     1395.29(12)
_cell_formula_units_Z            2
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    9793
_cell_measurement_theta_min      3.05
_cell_measurement_theta_max      79.55

_exptl_crystal_description       needle
_exptl_crystal_colour            yellow
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.214
_exptl_crystal_F_000             552
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.263
_exptl_crystal_size_mid          0.087
_exptl_crystal_size_min          0.075
_exptl_absorpt_coefficient_mu    1.397
_shelx_estimated_absorpt_T_min   0.710
_shelx_estimated_absorpt_T_max   0.902
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.55
_exptl_absorpt_correction_T_max  0.75
_exptl_absorpt_process_details   
; 
 TWINABS
 R.H. Blessing, Acta Cryst. (1995) A51 33-38 
;
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     1.54178
_diffrn_radiation_type           CuK\a
_diffrn_source                   'micro-focus sealed tube'
_diffrn_source_type              'INCOATEC I\mS 3.0'
_diffrn_radiation_monochromator  'multilayer mirror'
_diffrn_measurement_device_type  'Bruker D8 Venture (Photon II detector)'
_diffrn_measurement_method       'Data collection strategy APEX 3/Queen'
_diffrn_detector_area_resol_mean 7.3910
_diffrn_reflns_number            71276
_diffrn_reflns_av_unetI/netI     0.0347
_diffrn_reflns_av_R_equivalents  0.0683
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_l_min       0
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_theta_min         3.048
_diffrn_reflns_theta_max         79.538
_diffrn_reflns_theta_full        67.679
_diffrn_measured_fraction_theta_max 0.972
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.972
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.972
_diffrn_reflns_point_group_measured_fraction_full 0.999
_reflns_number_total             5871
_reflns_number_gt                5551
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
;
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;

_computing_data_collection       'Bruker APEX3(v2017.3-0)'
_computing_cell_refinement       'Bruker APEX3(v2017.3-0)'
_computing_data_reduction        'Bruker APEX3(v2017.3-0)'
_computing_structure_solution    'Bruker APEX3(v2017.3-0)'
_computing_structure_refinement  'SHELXL-2017/1 (Sheldrick, 2017)'
_computing_molecular_graphics    'ORTEP/PLATON (Spek)'
_computing_publication_material  'BRUKER AXS SHELXTL (c) 2008 / Vers. 2008/4'

_refine_special_details          
;
 Treatment of hydrogen atoms:    
 Riding model on idealized geometries 
 with the 1.2 fold isotropic displacement 
 parameters of the equivalent Uij of the 
 corresponding carbon atom.
 The methyl groups are idealized with
 tetrahedral angles in a combined 
 rotating and rigid group refinement
 with the 1.5 fold isotropic displacement
 parameters of the equivalent Uij of the 
 corresponding carbon atom. The NH hydrogen atom was refined freely.
 Disorder:
 The co-ordinated side arm is disordered over two positions Its corresponding
 bond lengths and angles were restrained to be equal (SADI) and RIGU restraints
 were applied to the anisotropic displacement parameters. For C8, c8', c12, and
 c12' additional SIMU restraints were used.
 Twinning:
 The crystal was a non-merohedral twin of two components. The model was refined
 against HKLF5 data.
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0492P)²+0.8905P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   diffmap
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         5871
_refine_ls_number_parameters     362
_refine_ls_number_restraints     52
_refine_ls_R_factor_all          0.0421
_refine_ls_R_factor_gt           0.0380
_refine_ls_wR_factor_ref         0.1040
_refine_ls_wR_factor_gt          0.0990
_refine_ls_goodness_of_fit_ref   1.062
_refine_ls_restrained_S_all      1.092
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

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 0.05822(4) 0.76550(3) 0.74994(2) 0.02515(10) Uani 1 1 d . . . . .
O1 O 0.0854(2) 0.64607(13) 0.66947(11) 0.0265(3) Uani 1 1 d . . . . .
N1 N -0.0776(3) 0.69722(19) 0.85594(15) 0.0338(5) Uani 1 1 d . . . . .
N2 N 0.2250(3) 0.56212(16) 0.50880(13) 0.0238(4) Uani 1 1 d . . . . .
H2A H 0.202(4) 0.618(3) 0.539(2) 0.030(8) Uiso 1 1 d . . . . .
N3 N -0.1581(3) 0.89390(18) 0.70795(16) 0.0313(5) Uani 1 1 d D . . . .
N4 N 0.3875(3) 0.65796(17) 0.21893(13) 0.0273(4) Uani 1 1 d . . . . .
C1 C -0.0909(3) 0.5927(2) 0.86177(15) 0.0273(5) Uani 1 1 d . . . . .
C2 C -0.0154(3) 0.5213(2) 0.79310(16) 0.0270(5) Uani 1 1 d . . . . .
H2 H -0.015438 0.444157 0.810293 0.032 Uiso 1 1 calc R U . . .
C3 C 0.0596(3) 0.54736(18) 0.70311(15) 0.0223(4) Uani 1 1 d . . . . .
C4 C 0.1077(3) 0.45956(18) 0.64333(15) 0.0236(4) Uani 1 1 d . . . . .
H4 H 0.083384 0.389169 0.668169 0.028 Uiso 1 1 calc R U . . .
C5 C 0.1849(3) 0.46751(18) 0.55431(15) 0.0232(4) Uani 1 1 d . . . . .
C6 C -0.1962(4) 0.5438(2) 0.94377(18) 0.0381(6) Uani 1 1 d . . . . .
H6A H -0.172885 0.462048 0.943789 0.057 Uiso 1 1 calc R U . . .
H6B H -0.319610 0.577515 0.939631 0.057 Uiso 1 1 calc R U . . .
H6C H -0.164162 0.560214 1.000898 0.057 Uiso 1 1 calc R U . . .
C7 C 0.2281(3) 0.36705(19) 0.50145(16) 0.0294(5) Uani 1 1 d . . . . .
H7A H 0.163993 0.385242 0.447322 0.044 Uiso 1 1 calc R U . . .
H7B H 0.195858 0.303056 0.541152 0.044 Uiso 1 1 calc R U . . .
H7C H 0.352594 0.347440 0.481441 0.044 Uiso 1 1 calc R U . . .
C8 C -0.1984(13) 0.7743(7) 0.9186(8) 0.0265(17) Uani 0.605(8) 1 d D U P A 1
H8A H -0.147662 0.768047 0.976957 0.032 Uiso 0.605(8) 1 calc R U P A 1
H8AB H -0.309183 0.751312 0.933500 0.032 Uiso 0.605(8) 1 calc R U P A 1
C9 C -0.2327(6) 0.8969(4) 0.8735(3) 0.0268(11) Uani 0.605(8) 1 d D . P A 1
H9A H -0.316821 0.945485 0.915298 0.032 Uiso 0.605(8) 1 calc R U P A 1
H9AB H -0.123578 0.921996 0.864268 0.032 Uiso 0.605(8) 1 calc R U P A 1
C10 C -0.3036(5) 0.9106(4) 0.7805(3) 0.0247(10) Uani 0.605(8) 1 d D . P A 1
H10A H -0.372182 0.854613 0.781102 0.030 Uiso 0.605(8) 1 calc R U P A 1
H10B H -0.380089 0.986900 0.768928 0.030 Uiso 0.605(8) 1 calc R U P A 1
C11 C -0.2256(5) 0.8621(4) 0.6251(3) 0.0264(10) Uani 0.605(8) 1 d D . P A 1
H11A H -0.136600 0.858790 0.572013 0.040 Uiso 0.605(8) 1 calc R U P A 1
H11B H -0.330270 0.918993 0.609236 0.040 Uiso 0.605(8) 1 calc R U P A 1
H11C H -0.252777 0.788359 0.641515 0.040 Uiso 0.605(8) 1 calc R U P A 1
C12 C -0.1140(13) 1.0028(6) 0.6727(6) 0.0265(15) Uani 0.605(8) 1 d D U P A 1
H12A H -0.020503 0.991661 0.621931 0.040 Uiso 0.605(8) 1 calc R U P A 1
H12B H -0.076355 1.031852 0.722401 0.040 Uiso 0.605(8) 1 calc R U P A 1
H12C H -0.216123 1.057034 0.650316 0.040 Uiso 0.605(8) 1 calc R U P A 1
C8' C -0.1508(19) 0.7696(13) 0.9285(14) 0.032(3) Uani 0.395(8) 1 d D U P A 2
H8'A H -0.064760 0.806655 0.943567 0.039 Uiso 0.395(8) 1 calc R U P A 2
H8'B H -0.193792 0.726518 0.985126 0.039 Uiso 0.395(8) 1 calc R U P A 2
C9' C -0.2982(12) 0.8548(7) 0.8850(5) 0.042(2) Uani 0.395(8) 1 d D . P A 2
H9'A H -0.372303 0.813332 0.863652 0.050 Uiso 0.395(8) 1 calc R U P A 2
H9'B H -0.369515 0.899705 0.933245 0.050 Uiso 0.395(8) 1 calc R U P A 2
C10' C -0.2453(12) 0.9349(7) 0.8049(5) 0.041(2) Uani 0.395(8) 1 d D . P A 2
H10C H -0.164461 0.970903 0.826620 0.049 Uiso 0.395(8) 1 calc R U P A 2
H10D H -0.350319 0.995111 0.792589 0.049 Uiso 0.395(8) 1 calc R U P A 2
C11' C -0.2619(9) 0.8304(7) 0.6819(7) 0.041(2) Uani 0.395(8) 1 d D . P A 2
H11D H -0.378351 0.878195 0.675348 0.062 Uiso 0.395(8) 1 calc R U P A 2
H11E H -0.268721 0.766644 0.729349 0.062 Uiso 0.395(8) 1 calc R U P A 2
H11F H -0.210672 0.802264 0.623007 0.062 Uiso 0.395(8) 1 calc R U P A 2
C12' C -0.127(3) 0.9915(13) 0.6499(10) 0.044(4) Uani 0.395(8) 1 d D U P A 2
H12D H -0.064756 0.969504 0.590728 0.066 Uiso 0.395(8) 1 calc R U P A 2
H12E H -0.056525 1.026646 0.679773 0.066 Uiso 0.395(8) 1 calc R U P A 2
H12F H -0.237213 1.045196 0.639415 0.066 Uiso 0.395(8) 1 calc R U P A 2
C13 C 0.3209(3) 0.5698(2) 0.41741(15) 0.0258(5) Uani 1 1 d . . . . .
H13A H 0.265068 0.541075 0.373726 0.031 Uiso 1 1 calc R U . . .
H13B H 0.440500 0.522674 0.419656 0.031 Uiso 1 1 calc R U . . .
C14 C 0.3256(3) 0.6914(2) 0.38420(15) 0.0273(5) Uani 1 1 d . . . . .
H14A H 0.368521 0.722550 0.431701 0.033 Uiso 1 1 calc R U . . .
H14B H 0.206765 0.736581 0.375586 0.033 Uiso 1 1 calc R U . . .
C15 C 0.4421(3) 0.7012(2) 0.29344(15) 0.0288(5) Uani 1 1 d . . . . .
H15A H 0.442673 0.781407 0.274757 0.035 Uiso 1 1 calc R U . . .
H15B H 0.561917 0.659232 0.303282 0.035 Uiso 1 1 calc R U . . .
C16 C 0.2310(3) 0.7331(2) 0.18704(17) 0.0326(5) Uani 1 1 d . . . . .
H16A H 0.250987 0.808338 0.166854 0.049 Uiso 1 1 calc R U . . .
H16B H 0.136637 0.737706 0.237452 0.049 Uiso 1 1 calc R U . . .
H16C H 0.199775 0.704169 0.135282 0.049 Uiso 1 1 calc R U . . .
C17 C 0.5241(4) 0.6431(2) 0.14255(18) 0.0399(6) Uani 1 1 d . . . . .
H17A H 0.486831 0.611868 0.093906 0.060 Uiso 1 1 calc R U . . .
H17B H 0.628751 0.591215 0.164231 0.060 Uiso 1 1 calc R U . . .
H17C H 0.548806 0.716061 0.118005 0.060 Uiso 1 1 calc R U . . .
C18 C 0.3035(3) 0.78958(19) 0.75541(17) 0.0276(4) Uani 1 1 d . . . . .
C19 C 0.3089(3) 0.8778(2) 0.67906(15) 0.0226(4) Uani 1 1 d . . . . .
C20 C 0.2743(3) 0.97966(19) 0.71328(16) 0.0241(4) Uani 1 1 d . . . . .
C21 C 0.2485(3) 0.9610(2) 0.81174(16) 0.0280(5) Uani 1 1 d . . . . .
C22 C 0.2686(3) 0.8477(2) 0.83787(16) 0.0306(5) Uani 1 1 d . . . . .
C23 C 0.4206(4) 0.6719(2) 0.7546(3) 0.0493(7) Uani 1 1 d . . . . .
H23A H 0.382494 0.622438 0.807397 0.074 Uiso 1 1 calc R U . . .
H23B H 0.539925 0.674554 0.758498 0.074 Uiso 1 1 calc R U . . .
H23C H 0.415092 0.642584 0.697256 0.074 Uiso 1 1 calc R U . . .
C24 C 0.3434(3) 0.8576(3) 0.57945(17) 0.0353(6) Uani 1 1 d . . . . .
H24A H 0.356583 0.927283 0.540903 0.053 Uiso 1 1 calc R U . . .
H24B H 0.246320 0.833969 0.562192 0.053 Uiso 1 1 calc R U . . .
H24C H 0.449872 0.798405 0.570280 0.053 Uiso 1 1 calc R U . . .
C25 C 0.2597(4) 1.0932(2) 0.6575(2) 0.0393(6) Uani 1 1 d . . . . .
H25A H 0.294337 1.083498 0.592179 0.059 Uiso 1 1 calc R U . . .
H25B H 0.335499 1.132554 0.678497 0.059 Uiso 1 1 calc R U . . .
H25C H 0.139683 1.137592 0.665371 0.059 Uiso 1 1 calc R U . . .
C26 C 0.2044(4) 1.0526(3) 0.8739(2) 0.0474(8) Uani 1 1 d . . . . .
H26A H 0.302372 1.087203 0.869317 0.071 Uiso 1 1 calc R U . . .
H26B H 0.179680 1.020388 0.937740 0.071 Uiso 1 1 calc R U . . .
H26C H 0.102401 1.110020 0.855060 0.071 Uiso 1 1 calc R U . . .
C27 C 0.2656(5) 0.7887(4) 0.9352(2) 0.0567(9) Uani 1 1 d . . . . .
H27A H 0.182198 0.837106 0.976240 0.085 Uiso 1 1 calc R U . . .
H27B H 0.381052 0.772849 0.955459 0.085 Uiso 1 1 calc R U . . .
H27C H 0.231677 0.717783 0.936974 0.085 Uiso 1 1 calc R U . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;

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 1.9821(16) . ?
Zn1 N1 1.985(2) . ?
Zn1 C18 2.087(2) . ?
Zn1 N3 2.127(2) . ?
O1 C3 1.304(3) . ?
N1 C1 1.314(3) . ?
N1 C8' 1.46(2) . ?
N1 C8 1.495(13) . ?
N2 C5 1.350(3) . ?
N2 C13 1.457(3) . ?
N3 C11' 1.409(6) . ?
N3 C12' 1.428(11) . ?
N3 C10 1.463(4) . ?
N3 C12 1.482(6) . ?
N3 C11 1.548(4) . ?
N3 C10' 1.593(7) . ?
N4 C16 1.452(3) . ?
N4 C17 1.453(3) . ?
N4 C15 1.459(3) . ?
C1 C2 1.411(3) . ?
C1 C6 1.516(3) . ?
C2 C3 1.404(3) . ?
C3 C4 1.442(3) . ?
C4 C5 1.370(3) . ?
C5 C7 1.505(3) . ?
C8 C9 1.534(8) . ?
C9 C10 1.532(6) . ?
C8' C9' 1.517(11) . ?
C9' C10' 1.511(10) . ?
C13 C14 1.520(3) . ?
C14 C15 1.528(3) . ?
C18 C19 1.450(3) . ?
C18 C22 1.462(3) . ?
C18 C23 1.517(3) . ?
C19 C20 1.376(3) . ?
C19 C24 1.502(3) . ?
C20 C21 1.430(3) . ?
C20 C25 1.503(3) . ?
C21 C22 1.370(4) . ?
C21 C26 1.504(3) . ?
C22 C27 1.510(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 N1 96.37(8) . . ?
O1 Zn1 C18 107.63(8) . . ?
N1 Zn1 C18 123.83(10) . . ?
O1 Zn1 N3 105.16(8) . . ?
N1 Zn1 N3 94.34(9) . . ?
C18 Zn1 N3 124.98(8) . . ?
C3 O1 Zn1 121.24(14) . . ?
C1 N1 C8' 123.3(7) . . ?
C1 N1 C8 118.7(4) . . ?
C1 N1 Zn1 121.94(16) . . ?
C8' N1 Zn1 114.7(7) . . ?
C8 N1 Zn1 117.9(4) . . ?
C5 N2 C13 124.80(19) . . ?
C11' N3 C12' 120.5(6) . . ?
C10 N3 C12 109.9(4) . . ?
C10 N3 C11 106.5(3) . . ?
C12 N3 C11 103.9(4) . . ?
C11' N3 C10' 107.1(5) . . ?
C12' N3 C10' 106.4(8) . . ?
C11' N3 Zn1 101.7(3) . . ?
C12' N3 Zn1 118.4(8) . . ?
C10 N3 Zn1 112.7(2) . . ?
C12 N3 Zn1 113.0(4) . . ?
C11 N3 Zn1 110.17(18) . . ?
C10' N3 Zn1 100.6(3) . . ?
C16 N4 C17 109.8(2) . . ?
C16 N4 C15 110.94(19) . . ?
C17 N4 C15 110.4(2) . . ?
N1 C1 C2 123.4(2) . . ?
N1 C1 C6 120.3(2) . . ?
C2 C1 C6 116.2(2) . . ?
C3 C2 C1 129.6(2) . . ?
O1 C3 C2 124.4(2) . . ?
O1 C3 C4 117.92(19) . . ?
C2 C3 C4 117.7(2) . . ?
C5 C4 C3 126.5(2) . . ?
N2 C5 C4 123.9(2) . . ?
N2 C5 C7 116.3(2) . . ?
C4 C5 C7 119.8(2) . . ?
N1 C8 C9 111.0(8) . . ?
C10 C9 C8 111.7(5) . . ?
N3 C10 C9 108.7(4) . . ?
N1 C8' C9' 102.4(11) . . ?
C10' C9' C8' 115.6(11) . . ?
C9' C10' N3 122.1(6) . . ?
N2 C13 C14 110.05(18) . . ?
C13 C14 C15 111.58(19) . . ?
N4 C15 C14 113.1(2) . . ?
C19 C18 C22 104.71(19) . . ?
C19 C18 C23 122.9(2) . . ?
C22 C18 C23 121.2(2) . . ?
C19 C18 Zn1 99.94(15) . . ?
C22 C18 Zn1 99.69(15) . . ?
C23 C18 Zn1 103.59(18) . . ?
C20 C19 C18 108.96(19) . . ?
C20 C19 C24 127.0(2) . . ?
C18 C19 C24 124.0(2) . . ?
C19 C20 C21 108.8(2) . . ?
C19 C20 C25 126.3(2) . . ?
C21 C20 C25 124.9(2) . . ?
C22 C21 C20 108.4(2) . . ?
C22 C21 C26 127.1(3) . . ?
C20 C21 C26 124.5(3) . . ?
C21 C22 C18 109.1(2) . . ?
C21 C22 C27 126.8(3) . . ?
C18 C22 C27 124.1(3) . . ?

_refine_diff_density_max         0.378
_refine_diff_density_min         -0.502
_refine_diff_density_rms         0.070

