# Electronic Supplementary Material (ESI) for ChemComm.
# This journal is © The Royal Society of Chemistry 2020

####################################################################### 
# 
# 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_lb_063m

_database_code_depnum_ccdc_archive 'CCDC 1992725'
loop_
_audit_author_name
_audit_author_address
'Christoph Wolper'
;Universitaet Duisburg Essen
Germany
;
_audit_update_record             
;
2020-03-25 deposited with the CCDC.	2020-06-24 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            'C33 H47 N O Zn2'
_chemical_formula_weight         604.45

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      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 21/c'
_space_group_name_Hall           '-P 2ybc'

_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+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'

_cell_length_a                   15.9994(14)
_cell_length_b                   13.4294(12)
_cell_length_c                   15.3641(13)
_cell_angle_alpha                90
_cell_angle_beta                 108.019(4)
_cell_angle_gamma                90
_cell_volume                     3139.3(5)
_cell_formula_units_Z            4
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    9708
_cell_measurement_theta_min      3.02
_cell_measurement_theta_max      33.20

_exptl_crystal_description       needle
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.279
_exptl_crystal_F_000             1280
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.850
_exptl_crystal_size_mid          0.298
_exptl_crystal_size_min          0.120
_exptl_absorpt_coefficient_mu    1.552
_shelx_estimated_absorpt_T_min   0.352
_shelx_estimated_absorpt_T_max   0.836
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.51
_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 2/COSMO'
_diffrn_detector_area_resol_mean 512
_diffrn_reflns_number            74019
_diffrn_reflns_av_unetI/netI     0.0260
_diffrn_reflns_av_R_equivalents  0.0364
_diffrn_reflns_limit_h_min       -24
_diffrn_reflns_limit_h_max       24
_diffrn_reflns_limit_k_min       -20
_diffrn_reflns_limit_k_max       19
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_theta_min         2.023
_diffrn_reflns_theta_max         33.272
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.938
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.938
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.938
_diffrn_reflns_point_group_measured_fraction_full 0.999
_reflns_number_total             11349
_reflns_number_gt                9683
_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 APEX2(v2009.5-1)'
_computing_cell_refinement       'BRUKER APEX2(v2009.5-1)'
_computing_data_reduction        'BRUKER APEX2(v2009.5-1)'
_computing_structure_solution    'BRUKER APEX2(v2009.5-1)'
_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)+(0.0504P)²+1.7411P] 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         11349
_refine_ls_number_parameters     348
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0430
_refine_ls_R_factor_gt           0.0352
_refine_ls_wR_factor_ref         0.1000
_refine_ls_wR_factor_gt          0.0956
_refine_ls_goodness_of_fit_ref   1.054
_refine_ls_restrained_S_all      1.054
_refine_ls_shift/su_max          0.001
_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 0.71513(2) 0.56363(2) 0.24918(2) 0.01975(5) Uani 1 1 d . . . . .
Zn2 Zn 0.83441(2) 0.48444(2) 0.22763(2) 0.02449(5) Uani 1 1 d . . . . .
O1 O 0.53765(7) 0.69395(8) 0.35098(7) 0.02086(19) Uani 1 1 d . . . . .
N1 N 0.66398(7) 0.62985(9) 0.33122(7) 0.01600(19) Uani 1 1 d . . . . .
C1 C 0.57720(8) 0.65026(9) 0.30506(8) 0.0139(2) Uani 1 1 d . . . . .
C2 C 0.52790(8) 0.61116(9) 0.20722(8) 0.0137(2) Uani 1 1 d . . . . .
C3 C 0.56840(8) 0.65100(9) 0.13652(8) 0.0148(2) Uani 1 1 d . . . . .
C4 C 0.59724(8) 0.57454(10) 0.09573(9) 0.0157(2) Uani 1 1 d . . . . .
C5 C 0.57941(8) 0.47915(9) 0.13607(9) 0.0156(2) Uani 1 1 d . . . . .
C6 C 0.54028(8) 0.49955(9) 0.20093(9) 0.0151(2) Uani 1 1 d . . . . .
C7 C 0.42992(8) 0.63791(11) 0.18204(9) 0.0194(2) Uani 1 1 d . . . . .
H7A H 0.423431 0.710414 0.183245 0.029 Uiso 1 1 calc R U . . .
H7B H 0.404776 0.607422 0.226268 0.029 Uiso 1 1 calc R U . . .
H7C H 0.399056 0.612953 0.120532 0.029 Uiso 1 1 calc R U . . .
C8 C 0.56834(10) 0.75905(10) 0.11431(10) 0.0206(2) Uani 1 1 d . . . . .
H8A H 0.593695 0.768445 0.064412 0.031 Uiso 1 1 calc R U . . .
H8B H 0.603437 0.795595 0.168512 0.031 Uiso 1 1 calc R U . . .
H8C H 0.507866 0.784148 0.095391 0.031 Uiso 1 1 calc R U . . .
C9 C 0.63547(9) 0.57913(11) 0.01801(9) 0.0212(3) Uani 1 1 d . . . . .
H9A H 0.643271 0.648868 0.003406 0.032 Uiso 1 1 calc R U . . .
H9B H 0.595566 0.546234 -0.035828 0.032 Uiso 1 1 calc R U . . .
H9C H 0.692533 0.545282 0.035756 0.032 Uiso 1 1 calc R U . . .
C10 C 0.59864(9) 0.37912(10) 0.10385(10) 0.0214(2) Uani 1 1 d . . . . .
H10A H 0.662014 0.372646 0.114349 0.032 Uiso 1 1 calc R U . . .
H10B H 0.567423 0.372200 0.038327 0.032 Uiso 1 1 calc R U . . .
H10C H 0.579085 0.326989 0.137762 0.032 Uiso 1 1 calc R U . . .
C11 C 0.50829(10) 0.42683(10) 0.25692(10) 0.0217(3) Uani 1 1 d . . . . .
H11A H 0.492729 0.364127 0.223147 0.033 Uiso 1 1 calc R U . . .
H11B H 0.456408 0.454022 0.269599 0.033 Uiso 1 1 calc R U . . .
H11C H 0.554731 0.414603 0.314765 0.033 Uiso 1 1 calc R U . . .
C12 C 0.90046(12) 0.38568(17) 0.15156(12) 0.0399(5) Uani 1 1 d . . . . .
C13 C 0.95910(11) 0.46281(15) 0.19616(13) 0.0338(4) Uani 1 1 d . . . . .
C14 C 0.97755(10) 0.44985(14) 0.29210(12) 0.0303(3) Uani 1 1 d . . . . .
C15 C 0.93071(11) 0.36470(14) 0.30543(12) 0.0317(3) Uani 1 1 d . . . . .
C16 C 0.88280(12) 0.32575(14) 0.21884(15) 0.0375(4) Uani 1 1 d . . . . .
C17 C 0.8676(2) 0.3660(3) 0.04998(16) 0.0812(12) Uani 1 1 d . . . . .
H17A H 0.807776 0.339177 0.033376 0.122 Uiso 1 1 calc R U . . .
H17B H 0.906288 0.317717 0.033791 0.122 Uiso 1 1 calc R U . . .
H17C H 0.867442 0.428338 0.016753 0.122 Uiso 1 1 calc R U . . .
C18 C 1.00061(17) 0.5387(2) 0.1516(2) 0.0714(10) Uani 1 1 d . . . . .
H18A H 0.971075 0.538429 0.085356 0.107 Uiso 1 1 calc R U . . .
H18B H 1.062952 0.522743 0.163772 0.107 Uiso 1 1 calc R U . . .
H18C H 0.995028 0.604790 0.176272 0.107 Uiso 1 1 calc R U . . .
C19 C 1.03759(15) 0.5128(2) 0.3662(2) 0.0600(7) Uani 1 1 d . . . . .
H19A H 1.020916 0.583015 0.355025 0.090 Uiso 1 1 calc R U . . .
H19B H 1.098381 0.503976 0.366125 0.090 Uiso 1 1 calc R U . . .
H19C H 1.032655 0.492611 0.425665 0.090 Uiso 1 1 calc R U . . .
C20 C 0.93202(18) 0.3222(2) 0.39604(17) 0.0571(7) Uani 1 1 d . . . . .
H20A H 0.946330 0.374892 0.442423 0.086 Uiso 1 1 calc R U . . .
H20B H 0.976467 0.269506 0.413745 0.086 Uiso 1 1 calc R U . . .
H20C H 0.874134 0.294353 0.391196 0.086 Uiso 1 1 calc R U . . .
C21 C 0.82420(17) 0.23469(18) 0.2025(3) 0.0765(10) Uani 1 1 d . . . . .
H21A H 0.800235 0.226537 0.253591 0.115 Uiso 1 1 calc R U . . .
H21B H 0.858571 0.175606 0.198015 0.115 Uiso 1 1 calc R U . . .
H21C H 0.775853 0.242970 0.145437 0.115 Uiso 1 1 calc R U . . .
C22 C 0.71704(8) 0.66016(10) 0.42046(8) 0.0168(2) Uani 1 1 d . . . . .
C23 C 0.71363(9) 0.60567(10) 0.49820(9) 0.0188(2) Uani 1 1 d . . . . .
C24 C 0.76505(10) 0.63799(12) 0.58410(9) 0.0243(3) Uani 1 1 d . . . . .
H24 H 0.762639 0.602977 0.637000 0.029 Uiso 1 1 calc R U . . .
C25 C 0.81960(10) 0.71994(13) 0.59425(10) 0.0268(3) Uani 1 1 d . . . . .
H25 H 0.853151 0.741767 0.653592 0.032 Uiso 1 1 calc R U . . .
C26 C 0.82501(10) 0.76988(12) 0.51753(10) 0.0245(3) Uani 1 1 d . . . . .
H26 H 0.863800 0.824973 0.524718 0.029 Uiso 1 1 calc R U . . .
C27 C 0.77467(9) 0.74104(11) 0.42976(9) 0.0188(2) Uani 1 1 d . . . . .
C28 C 0.65918(10) 0.51086(11) 0.48725(10) 0.0213(2) Uani 1 1 d . . . . .
H28 H 0.604358 0.521166 0.434837 0.026 Uiso 1 1 calc R U . . .
C29 C 0.71001(12) 0.42409(12) 0.46204(12) 0.0290(3) Uani 1 1 d . . . . .
H29A H 0.723414 0.440196 0.405580 0.044 Uiso 1 1 calc R U . . .
H29B H 0.674107 0.363562 0.452772 0.044 Uiso 1 1 calc R U . . .
H29C H 0.764905 0.413212 0.511708 0.044 Uiso 1 1 calc R U . . .
C30 C 0.63167(14) 0.48244(13) 0.57103(12) 0.0333(4) Uani 1 1 d . . . . .
H30A H 0.684099 0.467218 0.622505 0.050 Uiso 1 1 calc R U . . .
H30B H 0.593379 0.423807 0.556692 0.050 Uiso 1 1 calc R U . . .
H30C H 0.599936 0.538120 0.587501 0.050 Uiso 1 1 calc R U . . .
C31 C 0.78504(9) 0.79853(11) 0.34845(9) 0.0210(2) Uani 1 1 d . . . . .
H31 H 0.748086 0.765169 0.291298 0.025 Uiso 1 1 calc R U . . .
C32 C 0.75241(14) 0.90539(14) 0.34801(12) 0.0358(4) Uani 1 1 d . . . . .
H32A H 0.690582 0.904824 0.345990 0.054 Uiso 1 1 calc R U . . .
H32B H 0.758088 0.940364 0.294144 0.054 Uiso 1 1 calc R U . . .
H32C H 0.787598 0.939591 0.403625 0.054 Uiso 1 1 calc R U . . .
C33 C 0.88052(11) 0.79658(16) 0.34807(12) 0.0342(4) Uani 1 1 d . . . . .
H33A H 0.918422 0.826209 0.404874 0.051 Uiso 1 1 calc R U . . .
H33B H 0.885731 0.834727 0.295622 0.051 Uiso 1 1 calc R U . . .
H33C H 0.898563 0.727546 0.343472 0.051 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 1.9202(11) . ?
Zn1 Zn2 2.2963(3) . ?
Zn1 C4 2.5272(13) . ?
Zn1 C5 2.5861(12) . ?
Zn2 C13 2.2124(15) . ?
Zn2 C12 2.2373(16) . ?
Zn2 C14 2.2446(15) . ?
Zn2 C16 2.2856(18) . ?
Zn2 C15 2.2911(16) . ?
O1 C1 1.2323(15) . ?
N1 C1 1.3489(16) . ?
N1 C22 1.4305(16) . ?
C1 C2 1.5569(17) . ?
C2 C6 1.5188(17) . ?
C2 C3 1.5237(17) . ?
C2 C7 1.5366(17) . ?
C3 C4 1.3561(17) . ?
C3 C8 1.4906(18) . ?
C4 C5 1.4885(18) . ?
C4 C9 1.5018(18) . ?
C5 C6 1.3587(17) . ?
C5 C10 1.4962(18) . ?
C6 C11 1.4927(18) . ?
C12 C16 1.406(3) . ?
C12 C13 1.423(3) . ?
C12 C17 1.508(3) . ?
C13 C14 1.422(3) . ?
C13 C18 1.494(3) . ?
C14 C15 1.416(3) . ?
C14 C19 1.502(3) . ?
C15 C16 1.414(3) . ?
C15 C20 1.499(3) . ?
C16 C21 1.514(3) . ?
C22 C27 1.4032(19) . ?
C22 C23 1.4161(19) . ?
C23 C24 1.3912(19) . ?
C23 C28 1.522(2) . ?
C24 C25 1.383(2) . ?
C25 C26 1.382(2) . ?
C26 C27 1.3947(18) . ?
C27 C31 1.5206(19) . ?
C28 C30 1.532(2) . ?
C28 C29 1.537(2) . ?
C31 C32 1.526(2) . ?
C31 C33 1.530(2) . ?

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 Zn2 148.32(3) . . ?
N1 Zn1 C4 103.82(4) . . ?
Zn2 Zn1 C4 107.82(3) . . ?
N1 Zn1 C5 101.80(4) . . ?
Zn2 Zn1 C5 105.21(3) . . ?
C4 Zn1 C5 33.82(4) . . ?
C13 Zn2 C12 37.30(8) . . ?
C13 Zn2 C14 37.19(7) . . ?
C12 Zn2 C14 61.67(7) . . ?
C13 Zn2 C16 61.31(7) . . ?
C12 Zn2 C16 36.20(8) . . ?
C14 Zn2 C16 61.00(7) . . ?
C13 Zn2 C15 61.02(6) . . ?
C12 Zn2 C15 60.42(6) . . ?
C14 Zn2 C15 36.38(7) . . ?
C16 Zn2 C15 36.00(7) . . ?
C13 Zn2 Zn1 159.72(5) . . ?
C12 Zn2 Zn1 153.86(5) . . ?
C14 Zn2 Zn1 144.31(5) . . ?
C16 Zn2 Zn1 138.78(5) . . ?
C15 Zn2 Zn1 134.80(4) . . ?
C1 N1 C22 118.60(10) . . ?
C1 N1 Zn1 120.46(8) . . ?
C22 N1 Zn1 120.93(8) . . ?
O1 C1 N1 126.14(12) . . ?
O1 C1 C2 121.12(11) . . ?
N1 C1 C2 112.74(10) . . ?
C6 C2 C3 102.04(10) . . ?
C6 C2 C7 110.96(10) . . ?
C3 C2 C7 111.35(10) . . ?
C6 C2 C1 110.93(10) . . ?
C3 C2 C1 111.70(10) . . ?
C7 C2 C1 109.69(10) . . ?
C4 C3 C8 127.41(12) . . ?
C4 C3 C2 110.13(11) . . ?
C8 C3 C2 122.33(11) . . ?
C3 C4 C5 108.83(11) . . ?
C3 C4 C9 128.09(12) . . ?
C5 C4 C9 122.95(11) . . ?
C3 C4 Zn1 82.83(8) . . ?
C5 C4 Zn1 75.26(7) . . ?
C9 C4 Zn1 111.96(8) . . ?
C6 C5 C4 108.84(11) . . ?
C6 C5 C10 127.75(12) . . ?
C4 C5 C10 123.33(11) . . ?
C6 C5 Zn1 84.28(8) . . ?
C4 C5 Zn1 70.92(7) . . ?
C10 C5 Zn1 113.60(8) . . ?
C5 C6 C11 127.49(12) . . ?
C5 C6 C2 110.15(11) . . ?
C11 C6 C2 122.29(11) . . ?
C16 C12 C13 108.38(16) . . ?
C16 C12 C17 125.1(3) . . ?
C13 C12 C17 126.3(3) . . ?
C16 C12 Zn2 73.77(10) . . ?
C13 C12 Zn2 70.40(9) . . ?
C17 C12 Zn2 125.08(13) . . ?
C14 C13 C12 107.74(17) . . ?
C14 C13 C18 125.5(2) . . ?
C12 C13 C18 126.6(2) . . ?
C14 C13 Zn2 72.63(9) . . ?
C12 C13 Zn2 72.30(9) . . ?
C18 C13 Zn2 124.72(13) . . ?
C15 C14 C13 107.42(16) . . ?
C15 C14 C19 126.0(2) . . ?
C13 C14 C19 126.5(2) . . ?
C15 C14 Zn2 73.60(9) . . ?
C13 C14 Zn2 70.17(9) . . ?
C19 C14 Zn2 122.95(13) . . ?
C16 C15 C14 108.64(16) . . ?
C16 C15 C20 125.5(2) . . ?
C14 C15 C20 125.9(2) . . ?
C16 C15 Zn2 71.79(10) . . ?
C14 C15 Zn2 70.02(9) . . ?
C20 C15 Zn2 124.47(13) . . ?
C12 C16 C15 107.83(17) . . ?
C12 C16 C21 126.6(2) . . ?
C15 C16 C21 125.6(2) . . ?
C12 C16 Zn2 70.03(10) . . ?
C15 C16 Zn2 72.21(10) . . ?
C21 C16 Zn2 124.00(13) . . ?
C27 C22 C23 120.65(12) . . ?
C27 C22 N1 119.62(12) . . ?
C23 C22 N1 119.68(12) . . ?
C24 C23 C22 118.24(13) . . ?
C24 C23 C28 121.07(13) . . ?
C22 C23 C28 120.60(12) . . ?
C25 C24 C23 121.50(14) . . ?
C26 C25 C24 119.59(13) . . ?
C25 C26 C27 121.35(14) . . ?
C26 C27 C22 118.56(13) . . ?
C26 C27 C31 118.44(12) . . ?
C22 C27 C31 123.00(11) . . ?
C23 C28 C30 114.76(12) . . ?
C23 C28 C29 109.42(12) . . ?
C30 C28 C29 109.55(13) . . ?
C27 C31 C32 110.91(12) . . ?
C27 C31 C33 110.93(13) . . ?
C32 C31 C33 110.90(14) . . ?

_refine_diff_density_max         1.416
_refine_diff_density_min         -0.913
_refine_diff_density_rms         0.077


####################################################################### 
# 
# 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_lb_070m

_database_code_depnum_ccdc_archive 'CCDC 1992726'
loop_
_audit_author_name
_audit_author_address
'Christoph Wolper'
;Universitaet Duisburg Essen
Germany
;
_audit_update_record             
;
2020-03-25 deposited with the CCDC.	2020-06-24 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            'C25 H39 N O Zn2'
_chemical_formula_weight         500.31

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      monoclinic
_space_group_IT_number           11
_space_group_name_H-M_alt        'P 21/m'
_space_group_name_Hall           '-P 2yb'

_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+1/2, -z'
'-x, -y, -z'
'x, -y-1/2, z'

_cell_length_a                   9.0241(10)
_cell_length_b                   12.0224(13)
_cell_length_c                   12.0743(13)
_cell_angle_alpha                90
_cell_angle_beta                 110.467(5)
_cell_angle_gamma                90
_cell_volume                     1227.3(2)
_cell_formula_units_Z            2
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    9098
_cell_measurement_theta_min      2.47
_cell_measurement_theta_max      41.21

_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.354
_exptl_crystal_F_000             528
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.402
_exptl_crystal_size_mid          0.310
_exptl_crystal_size_min          0.218
_exptl_absorpt_coefficient_mu    1.969
_shelx_estimated_absorpt_T_min   0.505
_shelx_estimated_absorpt_T_max   0.673
_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 2/COSMO'
_diffrn_detector_area_resol_mean 512
_diffrn_reflns_number            89099
_diffrn_reflns_av_unetI/netI     0.0150
_diffrn_reflns_av_R_equivalents  0.0246
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_k_min       -22
_diffrn_reflns_limit_k_max       22
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_theta_min         1.800
_diffrn_reflns_theta_max         41.376
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.899
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.899
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.899
_diffrn_reflns_point_group_measured_fraction_full 0.999
_reflns_number_total             7688
_reflns_number_gt                6262
_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 APEX2(v2009.5-1)'
_computing_cell_refinement       'BRUKER APEX2(v2009.5-1)'
_computing_data_reduction        'BRUKER APEX2(v2009.5-1)'
_computing_structure_solution    'BRUKER APEX2(v2009.5-1)'
_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)+(0.0303P)²+0.3818P] 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         7688
_refine_ls_number_parameters     156
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0374
_refine_ls_R_factor_gt           0.0241
_refine_ls_wR_factor_ref         0.0695
_refine_ls_wR_factor_gt          0.0611
_refine_ls_goodness_of_fit_ref   1.082
_refine_ls_restrained_S_all      1.082
_refine_ls_shift/su_max          0.001
_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 0.09559(2) 0.250000 0.00863(2) 0.01602(3) Uani 1 2 d S T P . .
Zn2 Zn 0.03564(2) 0.250000 -0.19311(2) 0.01591(3) Uani 1 2 d S T P . .
O1 O -0.12822(12) 0.250000 -0.54873(7) 0.0302(2) Uani 1 2 d S T P . .
N1 N -0.10847(11) 0.250000 -0.35311(8) 0.01650(15) Uani 1 2 d S T P . .
C1 C -0.00438(14) 0.250000 0.15692(9) 0.01674(17) Uani 1 2 d S T P . .
C2 C 0.09282(10) 0.34595(6) 0.16887(6) 0.01819(13) Uani 1 1 d . . . . .
C3 C 0.25108(10) 0.30936(7) 0.19032(7) 0.01999(13) Uani 1 1 d . . . . .
C4 C -0.17597(16) 0.250000 0.14447(12) 0.0248(2) Uani 1 2 d S T P . .
H4A H -0.230657 0.310828 0.092058 0.037 Uiso 0.5 1 calc R U P . .
H4B H -0.185086 0.260264 0.222348 0.037 Uiso 0.5 1 calc R U P . .
H4C H -0.224077 0.178908 0.110869 0.037 Uiso 0.5 1 calc R U P . .
C5 C 0.04183(14) 0.46519(8) 0.16455(9) 0.02875(18) Uani 1 1 d . . . . .
H5A H 0.097353 0.509643 0.123232 0.043 Uiso 1 1 calc R U . . .
H5B H 0.067335 0.493394 0.245247 0.043 Uiso 1 1 calc R U . . .
H5C H -0.072510 0.470399 0.122361 0.043 Uiso 1 1 calc R U . . .
C6 C 0.39181(13) 0.38454(10) 0.21532(9) 0.0322(2) Uani 1 1 d . . . . .
H6A H 0.478482 0.343808 0.202478 0.048 Uiso 1 1 calc R U . . .
H6B H 0.425600 0.409975 0.297540 0.048 Uiso 1 1 calc R U . . .
H6C H 0.363228 0.448913 0.162260 0.048 Uiso 1 1 calc R U . . .
C7 C -0.05086(13) 0.250000 -0.44207(9) 0.01908(19) Uani 1 2 d S T P . .
C8 C 0.13405(13) 0.250000 -0.40005(9) 0.01932(19) Uani 1 2 d S T P . .
C9 C 0.20398(10) 0.34855(7) -0.32029(7) 0.01964(13) Uani 1 1 d . . . . .
C10 C 0.30186(9) 0.31182(7) -0.21374(7) 0.01822(13) Uani 1 1 d . . . . .
C11 C 0.18508(16) 0.250000 -0.50859(11) 0.0328(3) Uani 1 2 d S T P . .
H11C H 0.150670 0.319319 -0.552842 0.049 Uiso 0.5 1 calc R U P . .
H11A H 0.136676 0.186602 -0.559372 0.049 Uiso 0.5 1 calc R U P . .
H11B H 0.300513 0.244080 -0.482921 0.049 Uiso 0.5 1 calc R U P . .
C12 C 0.17084(14) 0.46550(9) -0.36273(10) 0.0326(2) Uani 1 1 d . . . . .
H12A H 0.208201 0.477424 -0.428874 0.049 Uiso 1 1 calc R U . . .
H12B H 0.225816 0.516619 -0.298208 0.049 Uiso 1 1 calc R U . . .
H12C H 0.056726 0.479346 -0.388999 0.049 Uiso 1 1 calc R U . . .
C13 C 0.40310(11) 0.37872(9) -0.11046(8) 0.02685(17) Uani 1 1 d . . . . .
H13A H 0.514833 0.365625 -0.098504 0.040 Uiso 1 1 calc R U . . .
H13B H 0.381853 0.356423 -0.039379 0.040 Uiso 1 1 calc R U . . .
H13C H 0.378922 0.457914 -0.125881 0.040 Uiso 1 1 calc R U . . .
C14 C -0.28331(13) 0.250000 -0.38253(9) 0.01638(16) Uani 1 2 d S T P . .
C15 C -0.31716(15) 0.250000 -0.26720(11) 0.0222(2) Uani 1 2 d S T P . .
H15A H -0.431341 0.243254 -0.284750 0.033 Uiso 0.5 1 calc R U P . .
H15B H -0.279101 0.319673 -0.224618 0.033 Uiso 0.5 1 calc R U P . .
H15C H -0.262779 0.187074 -0.218172 0.033 Uiso 0.5 1 calc R U P . .
C16 C -0.35665(11) 0.35515(9) -0.45166(9) 0.02690(17) Uani 1 1 d . . . . .
H16A H -0.339665 0.355458 -0.527509 0.040 Uiso 1 1 calc R U . . .
H16B H -0.306797 0.420975 -0.405864 0.040 Uiso 1 1 calc R U . . .
H16C H -0.470404 0.356298 -0.465832 0.040 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 C2 2.2602(7) . ?
Zn1 C2 2.2603(7) 4_565 ?
Zn1 C3 2.2668(8) . ?
Zn1 C3 2.2668(8) 4_565 ?
Zn1 C1 2.2693(10) . ?
Zn1 Zn2 2.3031(3) . ?
Zn2 N1 1.9148(9) . ?
O1 C7 1.2317(14) . ?
N1 C7 1.3471(13) . ?
N1 C14 1.4911(14) . ?
C1 C2 1.4257(11) . ?
C1 C2 1.4257(11) 4_565 ?
C1 C4 1.5024(18) . ?
C2 C3 1.4288(13) . ?
C2 C5 1.5009(12) . ?
C3 C3 1.4274(18) 4_565 ?
C3 C6 1.5009(13) . ?
C7 C8 1.5652(16) . ?
C8 C9 1.5181(11) . ?
C8 C9 1.5181(11) 4_565 ?
C8 C11 1.5335(15) . ?
C9 C10 1.3548(11) . ?
C9 C12 1.4905(14) . ?
C10 C10 1.4865(17) 4_565 ?
C10 C13 1.4966(12) . ?
C14 C15 1.5265(15) . ?
C14 C16 1.5318(11) . ?
C14 C16 1.5319(11) 4_565 ?

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
C2 Zn1 C2 61.38(4) . 4_565 ?
C2 Zn1 C3 36.79(3) . . ?
C2 Zn1 C3 61.35(3) 4_565 . ?
C2 Zn1 C3 61.35(3) . 4_565 ?
C2 Zn1 C3 36.80(3) 4_565 4_565 ?
C3 Zn1 C3 36.70(5) . 4_565 ?
C2 Zn1 C1 36.69(3) . . ?
C2 Zn1 C1 36.69(3) 4_565 . ?
C3 Zn1 C1 61.23(4) . . ?
C3 Zn1 C1 61.23(4) 4_565 . ?
C2 Zn1 Zn2 146.77(2) . . ?
C2 Zn1 Zn2 146.77(2) 4_565 . ?
C3 Zn1 Zn2 149.38(2) . . ?
C3 Zn1 Zn2 149.38(2) 4_565 . ?
C1 Zn1 Zn2 145.42(3) . . ?
N1 Zn2 Zn1 153.20(3) . . ?
C7 N1 C14 118.76(9) . . ?
C7 N1 Zn2 119.29(8) . . ?
C14 N1 Zn2 121.95(6) . . ?
C2 C1 C2 108.03(10) . 4_565 ?
C2 C1 C4 125.89(5) . . ?
C2 C1 C4 125.89(5) 4_565 . ?
C2 C1 Zn1 71.31(5) . . ?
C2 C1 Zn1 71.31(5) 4_565 . ?
C4 C1 Zn1 126.95(8) . . ?
C1 C2 C3 108.05(7) . . ?
C1 C2 C5 126.80(8) . . ?
C3 C2 C5 125.12(8) . . ?
C1 C2 Zn1 72.00(5) . . ?
C3 C2 Zn1 71.85(4) . . ?
C5 C2 Zn1 123.56(6) . . ?
C3 C3 C2 107.93(5) 4_565 . ?
C3 C3 C6 127.02(6) 4_565 . ?
C2 C3 C6 124.95(9) . . ?
C3 C3 Zn1 71.65(2) 4_565 . ?
C2 C3 Zn1 71.35(4) . . ?
C6 C3 Zn1 125.32(6) . . ?
O1 C7 N1 126.73(11) . . ?
O1 C7 C8 119.29(9) . . ?
N1 C7 C8 113.98(9) . . ?
C9 C8 C9 102.61(9) . 4_565 ?
C9 C8 C11 111.08(6) . . ?
C9 C8 C11 111.08(6) 4_565 . ?
C9 C8 C7 111.42(6) . . ?
C9 C8 C7 111.42(6) 4_565 . ?
C11 C8 C7 109.13(9) . . ?
C10 C9 C12 128.30(9) . . ?
C10 C9 C8 109.66(8) . . ?
C12 C9 C8 121.95(8) . . ?
C9 C10 C10 109.02(5) . 4_565 ?
C9 C10 C13 128.42(9) . . ?
C10 C10 C13 122.51(5) 4_565 . ?
N1 C14 C15 108.37(9) . . ?
N1 C14 C16 110.45(6) . . ?
C15 C14 C16 108.12(6) . . ?
N1 C14 C16 110.45(6) . 4_565 ?
C15 C14 C16 108.12(6) . 4_565 ?
C16 C14 C16 111.23(11) . 4_565 ?

_refine_diff_density_max         0.827
_refine_diff_density_min         -0.475
_refine_diff_density_rms         0.072



