# Electronic Supplementary Material (ESI) for Green Chemistry.
# This journal is © The Royal Society of Chemistry 2018

####################################################################### 
# 
# 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_TMU-47
_database_code_depnum_ccdc_archive 'CCDC 1852195'
_audit_update_record             
;
2018-06-28 deposited with the CCDC.
2018-10-16 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2016/6
_shelx_SHELXL_version_number     2016/6
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C51 H37 F12 N5 O9 Zn2'
_chemical_formula_weight         1222.59

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'
F F 0.0171 0.0103 '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           15
_space_group_name_H-M_alt        'C 2/c'
_space_group_name_Hall           '-C 2yc'

_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+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'

_cell_length_a                   27.5380(19)
_cell_length_b                   7.8870(6)
_cell_length_c                   23.3280(16)
_cell_angle_alpha                90
_cell_angle_beta                 99.2400(10)
_cell_angle_gamma                90
_cell_volume                     5000.9(6)
_cell_formula_units_Z            4
_cell_measurement_temperature    150(2)
_cell_measurement_reflns_used    7155
_cell_measurement_theta_min      2.50
_cell_measurement_theta_max      24.66
_exptl_crystal_description       plate
_exptl_crystal_colour            'pale yellow'
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.624
_exptl_crystal_F_000             2472
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_min          0.003
_exptl_crystal_size_mid          0.010
_exptl_crystal_size_max          0.016
_exptl_absorpt_coefficient_mu    1.067
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   empirical
_exptl_absorpt_correction_T_min  0.6930
_exptl_absorpt_correction_T_max  0.7463
_exptl_absorpt_process_details   sadabs
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      150(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            57754
_diffrn_reflns_av_unetI/netI     0.0733
_diffrn_reflns_av_R_equivalents  0.0927
_diffrn_reflns_limit_h_min       -39
_diffrn_reflns_limit_h_max       39
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_l_min       -34
_diffrn_reflns_limit_l_max       34
_diffrn_reflns_theta_min         1.498
_diffrn_reflns_theta_max         31.785
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.947
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.947
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.947
_diffrn_reflns_point_group_measured_fraction_full 1.000
_reflns_number_total             8088
_reflns_number_gt                5089
_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       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    ?
_computing_structure_refinement  'SHELXL-2016/6 (Sheldrick, 2016)'
_computing_molecular_graphics    ?
_computing_publication_material  ?
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0687P)²+7.9436P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         8088
_refine_ls_number_parameters     349
_refine_ls_number_restraints     4
_refine_ls_R_factor_all          0.1107
_refine_ls_R_factor_gt           0.0568
_refine_ls_wR_factor_ref         0.1470
_refine_ls_wR_factor_gt          0.1279
_refine_ls_goodness_of_fit_ref   1.033
_refine_ls_restrained_S_all      1.036
_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 0.53608(2) 0.13950(4) 0.00185(2) 0.01772(10) Uani 1 1 d . . . . .
F3 F 0.66751(8) -0.8377(3) -0.14071(9) 0.0365(5) Uani 1 1 d . . . . .
O4 O 0.56899(8) -0.0417(3) -0.04139(10) 0.0286(5) Uani 1 1 d . . . . .
F2 F 0.73075(8) -0.8015(3) -0.18254(10) 0.0443(5) Uani 1 1 d . . . . .
O3 O 0.48456(8) 0.2547(3) 0.04266(10) 0.0258(5) Uani 1 1 d . . . . .
C11 C 0.63154(12) -0.3235(4) 0.25100(13) 0.0266(7) Uani 1 1 d . . . . .
O1 O 0.55642(9) 0.0030(3) 0.07651(10) 0.0329(5) Uani 1 1 d . . . . .
F6 F 0.68050(9) -0.3528(3) -0.25736(9) 0.0440(5) Uani 1 1 d . . . . .
F1 F 0.72038(8) -0.6457(3) -0.11051(9) 0.0408(5) Uani 1 1 d . . . . .
F4 F 0.72174(9) -0.5776(3) -0.26842(10) 0.0515(6) Uani 1 1 d . . . . .
C23 C 0.69926(12) 0.7047(5) 0.02888(15) 0.0305(7) Uani 1 1 d . . . . .
C2 C 0.58379(10) -0.2919(4) -0.09106(12) 0.0187(5) Uani 1 1 d . . . . .
C3 C 0.56972(10) -0.4561(4) -0.10795(12) 0.0208(6) Uani 1 1 d . . . . .
H3 H 0.542208 -0.504336 -0.095966 0.025 Uiso 1 1 calc R U . . .
C17 C 0.54085(12) -0.1289(4) 0.09768(13) 0.0251(6) Uani 1 1 d . . . . .
O2 O 0.49621(9) 0.2120(3) -0.07585(10) 0.0311(5) Uani 1 1 d . . . . .
C1 C 0.55370(11) -0.1881(4) -0.05550(12) 0.0197(6) Uani 1 1 d . . . . .
N1 N 0.59136(9) 0.3115(3) 0.01548(11) 0.0207(5) Uani 1 1 d . . . . .
C5 C 0.59667(11) -0.5482(4) -0.14268(13) 0.0247(6) Uani 1 1 d . . . . .
H5 H 0.586861 -0.657674 -0.153902 0.030 Uiso 1 1 calc R U . . .
C8 C 0.66659(12) -0.5902(4) -0.19912(14) 0.0271(7) Uani 1 1 d . . . . .
C7 C 0.63815(11) -0.4792(4) -0.16101(13) 0.0225(6) Uani 1 1 d . . . . .
C6 C 0.65298(11) -0.3171(4) -0.14260(14) 0.0260(7) Uani 1 1 d . . . . .
H6 H 0.681175 -0.270377 -0.153382 0.031 Uiso 1 1 calc R U . . .
C18 C 0.63449(13) 0.2872(4) -0.00220(16) 0.0340(8) Uani 1 1 d . . . . .
H18 H 0.640035 0.183767 -0.019150 0.041 Uiso 1 1 calc R U . . .
N2 N 0.73419(11) 0.6804(4) 0.00030(15) 0.0405(8) Uani 1 1 d . . . . .
C16 C 0.57119(12) -0.1934(4) 0.15302(13) 0.0269(7) Uani 1 1 d . . . . .
C4 C 0.62588(11) -0.2245(4) -0.10815(13) 0.0235(6) Uani 1 1 d . . . . .
H4 H 0.636033 -0.115768 -0.096336 0.028 Uiso 1 1 calc R U . . .
C22 C 0.66325(12) 0.5632(4) 0.02761(14) 0.0280(7) Uani 1 1 d . . . . .
F5 F 0.74105(8) -0.4259(3) -0.19185(10) 0.0457(6) Uani 1 1 d . . . . .
C13 C 0.59123(13) -0.4146(5) 0.22369(14) 0.0314(7) Uani 1 1 d . . . . .
H13 H 0.584427 -0.520581 0.237965 0.038 Uiso 1 1 calc R U . . .
C19 C 0.58468(13) 0.4589(4) 0.04049(15) 0.0313(7) Uani 1 1 d . . . . .
H19 H 0.555136 0.477163 0.054026 0.038 Uiso 1 1 calc R U . . .
C12 C 0.64114(13) -0.1654(4) 0.22885(15) 0.0304(7) Uani 1 1 d . . . . .
H12 H 0.667918 -0.102301 0.246632 0.037 Uiso 1 1 calc R U . . .
C10 C 0.70282(13) -0.4847(5) -0.22927(16) 0.0364(9) Uani 1 1 d . . . . .
C21 C 0.61950(13) 0.5866(5) 0.04741(15) 0.0338(8) Uani 1 1 d . . . . .
H21 H 0.613271 0.687732 0.065391 0.041 Uiso 1 1 calc R U . . .
C14 C 0.61093(13) -0.1015(4) 0.18037(14) 0.0310(7) Uani 1 1 d . . . . .
H14 H 0.617539 0.004624 0.166084 0.037 Uiso 1 1 calc R U . . .
C15 C 0.56112(13) -0.3501(4) 0.17569(14) 0.0316(7) Uani 1 1 d . . . . .
H15 H 0.533902 -0.411873 0.158384 0.038 Uiso 1 1 calc R U . . .
C9 C 0.69671(12) -0.7200(5) -0.15828(15) 0.0317(8) Uani 1 1 d . . . . .
C20 C 0.67141(12) 0.4075(5) 0.00329(16) 0.0335(8) Uani 1 1 d . . . . .
H20 H 0.701179 0.384410 -0.009091 0.040 Uiso 1 1 calc R U . . .
C24 C 0.68994(17) 0.8619(6) 0.0603(2) 0.0640(15) Uani 1 1 d . . . . .
H24A H 0.661225 0.846969 0.078290 0.096 Uiso 1 1 calc R U . . .
H24B H 0.717792 0.885711 0.089591 0.096 Uiso 1 1 calc R U . . .
H24C H 0.684784 0.954752 0.033414 0.096 Uiso 1 1 calc R U . . .
C101 C 0.5347(3) 0.0339(9) 0.7911(3) 0.095(2) Uiso 1 1 d D . . . .
H10A H 0.516702 0.106712 0.813161 0.143 Uiso 1 1 calc R U . . .
H10B H 0.555235 -0.040830 0.817009 0.143 Uiso 1 1 calc R U . . .
H10C H 0.554870 0.101534 0.770045 0.143 Uiso 1 1 calc R U . . .
N100 N 0.500000 -0.0667(9) 0.750000 0.087(2) Uani 1 2 d DS T P . .
O100 O 0.4935(4) -0.3354(11) 0.7275(4) 0.100 Uiso 0.5 1 d D U P . .
C102 C 0.5115(5) -0.1821(16) 0.7120(6) 0.100 Uiso 0.5 1 d D U P . .
H102 H 0.528429 -0.162216 0.681225 0.120 Uiso 0.5 1 calc R U P . .


_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 2.026(2) . ?
Zn1 O4 2.043(2) . ?
Zn1 O3 2.044(2) . ?
Zn1 O2 2.044(2) . ?
Zn1 O1 2.048(2) . ?
Zn1 Zn1 2.9568(6) 5_655 ?
F3 C9 1.335(4) . ?
O4 C1 1.254(4) . ?
F2 C9 1.336(4) . ?
O3 C1 1.256(3) 5_655 ?
C11 C13 1.388(5) . ?
C11 C12 1.391(4) . ?
C11 C8 1.546(4) 6_546 ?
O1 C17 1.256(4) . ?
F6 C10 1.327(5) . ?
F1 C9 1.333(4) . ?
F4 C10 1.340(4) . ?
C23 N2 1.270(4) . ?
C23 C24 1.483(5) . ?
C23 C22 1.490(4) . ?
C2 C3 1.390(4) . ?
C2 C4 1.391(4) . ?
C2 C1 1.505(4) . ?
C3 C5 1.388(4) . ?
C17 O2 1.251(4) 5_655 ?
C17 C16 1.509(4) . ?
N1 C19 1.326(4) . ?
N1 C18 1.332(4) . ?
C5 C7 1.393(4) . ?
C8 C9 1.546(5) . ?
C8 C7 1.547(4) . ?
C8 C10 1.552(5) . ?
C7 C6 1.389(4) . ?
C6 C4 1.389(4) . ?
C18 C20 1.381(5) . ?
N2 N2 1.402(6) 7_665 ?
C16 C14 1.381(5) . ?
C16 C15 1.390(5) . ?
C22 C21 1.370(5) . ?
C22 C20 1.386(5) . ?
F5 C10 1.338(4) . ?
C13 C15 1.379(5) . ?
C19 C21 1.382(5) . ?
C12 C14 1.387(5) . ?
C101 N100 1.473(7) . ?
N100 C102 1.343(12) . ?
N100 C102 1.343(12) 2_656 ?
O100 O100 1.053(16) 2_656 ?
O100 C102 1.377(13) . ?
O100 C102 1.880(16) 2_656 ?
C102 C102 1.98(3) 2_656 ?

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 O4 99.46(9) . . ?
N1 Zn1 O3 100.92(9) . . ?
O4 Zn1 O3 159.52(9) . . ?
N1 Zn1 O2 103.58(10) . . ?
O4 Zn1 O2 88.60(10) . . ?
O3 Zn1 O2 88.54(9) . . ?
N1 Zn1 O1 97.05(10) . . ?
O4 Zn1 O1 88.26(10) . . ?
O3 Zn1 O1 87.31(10) . . ?
O2 Zn1 O1 159.37(10) . . ?
N1 Zn1 Zn1 170.94(8) . 5_655 ?
O4 Zn1 Zn1 79.30(6) . 5_655 ?
O3 Zn1 Zn1 80.26(6) . 5_655 ?
O2 Zn1 Zn1 85.39(7) . 5_655 ?
O1 Zn1 Zn1 73.99(7) . 5_655 ?
C1 O4 Zn1 128.06(19) . . ?
C1 O3 Zn1 126.65(19) 5_655 . ?
C13 C11 C12 118.6(3) . . ?
C13 C11 C8 118.3(3) . 6_546 ?
C12 C11 C8 122.8(3) . 6_546 ?
C17 O1 Zn1 134.9(2) . . ?
N2 C23 C24 126.3(3) . . ?
N2 C23 C22 115.7(3) . . ?
C24 C23 C22 117.9(3) . . ?
C3 C2 C4 118.8(3) . . ?
C3 C2 C1 120.7(2) . . ?
C4 C2 C1 120.5(3) . . ?
C5 C3 C2 120.1(3) . . ?
O2 C17 O1 125.6(3) 5_655 . ?
O2 C17 C16 118.3(3) 5_655 . ?
O1 C17 C16 116.0(3) . . ?
C17 O2 Zn1 120.1(2) 5_655 . ?
O4 C1 O3 125.5(3) . 5_655 ?
O4 C1 C2 117.0(3) . . ?
O3 C1 C2 117.4(3) 5_655 . ?
C19 N1 C18 117.1(3) . . ?
C19 N1 Zn1 120.1(2) . . ?
C18 N1 Zn1 122.7(2) . . ?
C3 C5 C7 121.1(3) . . ?
C11 C8 C9 112.4(3) 6_545 . ?
C11 C8 C7 111.7(3) 6_545 . ?
C9 C8 C7 106.9(3) . . ?
C11 C8 C10 105.3(3) 6_545 . ?
C9 C8 C10 108.3(3) . . ?
C7 C8 C10 112.3(3) . . ?
C6 C7 C5 118.6(3) . . ?
C6 C7 C8 123.2(3) . . ?
C5 C7 C8 118.1(3) . . ?
C4 C6 C7 120.3(3) . . ?
N1 C18 C20 123.5(3) . . ?
C23 N2 N2 114.3(4) . 7_665 ?
C14 C16 C15 118.9(3) . . ?
C14 C16 C17 120.5(3) . . ?
C15 C16 C17 120.6(3) . . ?
C6 C4 C2 121.0(3) . . ?
C21 C22 C20 117.8(3) . . ?
C21 C22 C23 120.7(3) . . ?
C20 C22 C23 121.4(3) . . ?
C15 C13 C11 120.9(3) . . ?
N1 C19 C21 123.2(3) . . ?
C14 C12 C11 120.2(3) . . ?
F6 C10 F5 107.7(3) . . ?
F6 C10 F4 107.0(3) . . ?
F5 C10 F4 106.4(3) . . ?
F6 C10 C8 111.3(3) . . ?
F5 C10 C8 112.7(3) . . ?
F4 C10 C8 111.4(3) . . ?
C22 C21 C19 119.6(3) . . ?
C16 C14 C12 120.9(3) . . ?
C13 C15 C16 120.4(3) . . ?
F1 C9 F3 106.7(3) . . ?
F1 C9 F2 106.5(3) . . ?
F3 C9 F2 107.1(3) . . ?
F1 C9 C8 111.5(3) . . ?
F3 C9 C8 111.1(3) . . ?
F2 C9 C8 113.7(3) . . ?
C18 C20 C22 118.8(3) . . ?
C102 N100 C102 94.7(13) . 2_656 ?
C102 N100 C101 97.6(7) . 2_656 ?
C102 N100 C101 126.7(7) 2_656 2_656 ?
C102 N100 C101 126.7(7) . . ?
C102 N100 C101 97.6(7) 2_656 . ?
C101 N100 C101 114.8(7) 2_656 . ?
O100 O100 C102 100.5(9) 2_656 . ?
O100 O100 C102 46.1(6) 2_656 2_656 ?
C102 O100 C102 72.8(10) . 2_656 ?
N100 C102 O100 106.8(11) . . ?
N100 C102 O100 83.5(9) . 2_656 ?
O100 C102 O100 33.4(6) . 2_656 ?
N100 C102 C102 42.6(6) . 2_656 ?
O100 C102 C102 65.4(7) . 2_656 ?
O100 C102 C102 41.8(5) 2_656 2_656 ?

_refine_diff_density_max         1.300
_refine_diff_density_min         -1.174
_refine_diff_density_rms         0.105



