# Electronic Supplementary Material (ESI) for ChemComm.
# This journal is © The Royal Society of Chemistry 2022

####################################################################### 
# 
# 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_1004
_database_code_depnum_ccdc_archive 'CCDC 2179410'
loop_
_audit_author_name
_audit_author_address
'Pierluigi Mercandelli'
;Universita degli Studi di Milano
Italy
;
_audit_update_record             
;
2022-06-15 deposited with the CCDC.	2022-07-27 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        
bis(1-(4-pyridyl)butane-1,3-dionato)(pyridine)copper(II)1,4-diiodo-2,3,5,6-tetrafluorobenzene
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C23 H21 Cu N3 O4, C6 F4 I2'
_chemical_formula_sum            'C29 H21 Cu F4 I2 N3 O4'
_chemical_formula_weight         868.83

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'
Cu Cu 0.3201 1.2651 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
I I -0.4742 1.8119 '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                   11.3975(12)
_cell_length_b                   13.8907(14)
_cell_length_c                   18.5409(19)
_cell_angle_alpha                90
_cell_angle_beta                 101.3540(10)
_cell_angle_gamma                90
_cell_volume                     2877.9(5)
_cell_formula_units_Z            4
_cell_measurement_temperature    150(2)
_cell_measurement_reflns_used    9878
_cell_measurement_theta_min      2.241
_cell_measurement_theta_max      31.208

_exptl_crystal_description       polyhedral
_exptl_crystal_colour            green
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    2.005
_exptl_crystal_F_000             1676
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.255
_exptl_crystal_size_mid          0.200
_exptl_crystal_size_min          0.070
_exptl_absorpt_coefficient_mu    2.972
_shelx_estimated_absorpt_T_min   0.518
_shelx_estimated_absorpt_T_max   0.819
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.7010
_exptl_absorpt_correction_T_max  0.8190
_exptl_absorpt_process_details   SADABS-2012/1
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      150(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Bruker APEX II'
_diffrn_measurement_method       'ω scans'
_diffrn_measurement_details      
;
A full sphere of reciprocal space was scanned by 0.5° ω steps,
collecting 4 sets of 360 frames each, at 10 s exposure, keeping the detector
at θ = 30° and at 5.0 cm from the sample.
;
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            42950
_diffrn_reflns_av_unetI/netI     0.0173
_diffrn_reflns_av_R_equivalents  0.0233
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_k_min       -19
_diffrn_reflns_limit_k_max       19
_diffrn_reflns_limit_l_min       -25
_diffrn_reflns_limit_l_max       25
_diffrn_reflns_theta_min         1.822
_diffrn_reflns_theta_max         29.835
_diffrn_reflns_theta_full        25.240
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_point_group_measured_fraction_full 1.000
_reflns_number_total             8257
_reflns_number_gt                7450
_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    SIR-2014
_computing_structure_refinement  SHELXL-2014/7
_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)+(0.0209P)²+4.2182P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         8257
_refine_ls_number_parameters     390
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0328
_refine_ls_R_factor_gt           0.0279
_refine_ls_wR_factor_ref         0.0635
_refine_ls_wR_factor_gt          0.0619
_refine_ls_goodness_of_fit_ref   1.192
_refine_ls_restrained_S_all      1.192
_refine_ls_shift/su_max          0.002
_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
Cu1 Cu 0.26438(3) 0.37489(2) 0.50879(2) 0.01806(6) Uani 1 1 d . . . . .
C1 C 0.4405(2) 0.3358(3) 0.32931(16) 0.0338(7) Uani 1 1 d . . . . .
H1 H 0.4964 0.2859 0.3522 0.051 Uiso 1 1 calc R U . . .
H2 H 0.4830 0.3972 0.3299 0.051 Uiso 1 1 calc R U . . .
H3 H 0.4068 0.3176 0.2784 0.051 Uiso 1 1 calc R U . . .
C2 C 0.3410(2) 0.3460(2) 0.37159(14) 0.0227(5) Uani 1 1 d . . . . .
C3 C 0.2234(2) 0.3516(2) 0.33149(14) 0.0274(6) Uani 1 1 d . . . . .
H4 H 0.2122 0.3508 0.2793 0.033 Uiso 1 1 calc R U . . .
C4 C 0.1218(2) 0.35824(17) 0.36219(13) 0.0177(4) Uani 1 1 d . . . . .
C5 C 0.0017(2) 0.36430(17) 0.31215(13) 0.0173(4) Uani 1 1 d . . . . .
C6 C -0.1013(2) 0.3556(2) 0.34151(14) 0.0244(5) Uani 1 1 d . . . . .
H5 H -0.0956 0.3474 0.3929 0.029 Uiso 1 1 calc R U . . .
C7 C -0.2121(2) 0.3592(2) 0.29493(15) 0.0285(6) Uani 1 1 d . . . . .
H6 H -0.2814 0.3529 0.3158 0.034 Uiso 1 1 calc R U . . .
C8 C -0.1281(2) 0.3810(2) 0.19481(15) 0.0286(6) Uani 1 1 d . . . . .
H7 H -0.1371 0.3904 0.1433 0.034 Uiso 1 1 calc R U . . .
C9 C -0.0132(2) 0.3785(2) 0.23648(14) 0.0239(5) Uani 1 1 d . . . . .
H8 H 0.0542 0.3863 0.2140 0.029 Uiso 1 1 calc R U . . .
C10 C 0.0890(2) 0.3719(2) 0.69011(15) 0.0307(6) Uani 1 1 d . . . . .
H9 H 0.0474 0.3100 0.6814 0.046 Uiso 1 1 calc R U . . .
H10 H 0.0324 0.4243 0.6739 0.046 Uiso 1 1 calc R U . . .
H11 H 0.1224 0.3791 0.7427 0.046 Uiso 1 1 calc R U . . .
C11 C 0.1882(2) 0.37557(19) 0.64770(14) 0.0212(5) Uani 1 1 d . . . . .
C12 C 0.3050(2) 0.3900(2) 0.68651(14) 0.0265(6) Uani 1 1 d . . . . .
H12 H 0.3157 0.4026 0.7377 0.032 Uiso 1 1 calc R U . . .
C13 C 0.4069(2) 0.38735(17) 0.65571(13) 0.0185(5) Uani 1 1 d . . . . .
C14 C 0.5281(2) 0.39396(18) 0.70563(13) 0.0186(4) Uani 1 1 d . . . . .
C15 C 0.6308(2) 0.3942(2) 0.67586(15) 0.0313(6) Uani 1 1 d . . . . .
H13 H 0.6248 0.3909 0.6241 0.038 Uiso 1 1 calc R U . . .
C16 C 0.7428(3) 0.3992(3) 0.72243(17) 0.0346(7) Uani 1 1 d . . . . .
H14 H 0.8119 0.3996 0.7010 0.042 Uiso 1 1 calc R U . . .
C17 C 0.6593(2) 0.4037(2) 0.82404(15) 0.0288(6) Uani 1 1 d . . . . .
H15 H 0.6680 0.4073 0.8760 0.035 Uiso 1 1 calc R U . . .
C18 C 0.5444(2) 0.3993(2) 0.78180(14) 0.0238(5) Uani 1 1 d . . . . .
H16 H 0.4770 0.3998 0.8049 0.029 Uiso 1 1 calc R U . . .
C19 C 0.1447(2) 0.5803(2) 0.47694(14) 0.0243(5) Uani 1 1 d . . . . .
H17 H 0.0751 0.5412 0.4652 0.029 Uiso 1 1 calc R U . . .
C20 C 0.1314(2) 0.6795(2) 0.47183(15) 0.0274(6) Uani 1 1 d . . . . .
H18 H 0.0543 0.7076 0.4578 0.033 Uiso 1 1 calc R U . . .
C21 C 0.2324(3) 0.7366(2) 0.48755(15) 0.0288(6) Uani 1 1 d . . . . .
H19 H 0.2262 0.8047 0.4843 0.035 Uiso 1 1 calc R U . . .
C22 C 0.3432(2) 0.6924(2) 0.50818(15) 0.0273(6) Uani 1 1 d . . . . .
H20 H 0.4143 0.7297 0.5188 0.033 Uiso 1 1 calc R U . . .
C23 C 0.3482(2) 0.5930(2) 0.51296(14) 0.0238(5) Uani 1 1 d . . . . .
H21 H 0.4241 0.5631 0.5278 0.029 Uiso 1 1 calc R U . . .
N1 N -0.2269(2) 0.37098(18) 0.22233(13) 0.0274(5) Uani 1 1 d . . . . .
N2 N 0.7579(2) 0.40334(18) 0.79571(13) 0.0277(5) Uani 1 1 d . . . . .
N3 N 0.25119(18) 0.53703(17) 0.49767(11) 0.0215(4) Uani 1 1 d . . . . .
O1 O 0.37140(16) 0.34962(15) 0.44107(10) 0.0242(4) Uani 1 1 d . . . . .
O2 O 0.12145(16) 0.35922(14) 0.43107(10) 0.0228(4) Uani 1 1 d . . . . .
O3 O 0.15839(16) 0.36330(14) 0.57870(9) 0.0224(4) Uani 1 1 d . . . . .
O4 O 0.40700(15) 0.37707(14) 0.58714(9) 0.0214(4) Uani 1 1 d . . . . .
C24 C 0.1524(2) 0.11539(17) 0.46271(13) 0.0191(5) Uani 1 1 d . . . . .
C25 C 0.2587(2) 0.10807(19) 0.43691(13) 0.0202(5) Uani 1 1 d . . . . .
C26 C 0.3695(2) 0.11353(18) 0.48346(14) 0.0197(5) Uani 1 1 d . . . . .
C27 C 0.3789(2) 0.12526(18) 0.55853(14) 0.0193(5) Uani 1 1 d . . . . .
C28 C 0.2734(2) 0.13322(19) 0.58445(13) 0.0213(5) Uani 1 1 d . . . . .
C29 C 0.1630(2) 0.12865(18) 0.53776(14) 0.0187(4) Uani 1 1 d . . . . .
F1 F 0.25616(14) 0.09638(13) 0.36445(8) 0.0296(4) Uani 1 1 d . . . . .
F2 F 0.46825(13) 0.10745(12) 0.45424(9) 0.0271(3) Uani 1 1 d . . . . .
F3 F 0.27622(14) 0.14553(13) 0.65696(8) 0.0299(4) Uani 1 1 d . . . . .
F4 F 0.06472(13) 0.13869(12) 0.56713(9) 0.0254(3) Uani 1 1 d . . . . .
I1 I -0.01489(2) 0.10624(2) 0.39211(2) 0.02098(4) Uani 1 1 d . . . . .
I2 I 0.54783(2) 0.12918(2) 0.62979(2) 0.02121(4) Uani 1 1 d . . . . .


_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
Cu1 O1 1.9469(18) . ?
Cu1 O2 1.9631(18) . ?
Cu1 O3 1.9447(18) . ?
Cu1 O4 1.9554(17) . ?
Cu1 N3 2.264(2) . ?
C1 C2 1.506(4) . ?
C2 O1 1.267(3) . ?
C2 C3 1.402(4) . ?
C3 C4 1.390(4) . ?
C4 O2 1.278(3) . ?
C4 C5 1.498(3) . ?
C5 C6 1.393(3) . ?
C5 C9 1.394(3) . ?
C6 C7 1.383(4) . ?
C7 N1 1.333(4) . ?
C8 N1 1.332(4) . ?
C8 C9 1.383(4) . ?
C10 C11 1.500(4) . ?
C11 O3 1.269(3) . ?
C11 C12 1.397(4) . ?
C12 C13 1.391(4) . ?
C13 O4 1.280(3) . ?
C13 C14 1.507(3) . ?
C14 C15 1.389(4) . ?
C14 C18 1.390(3) . ?
C15 C16 1.395(4) . ?
C16 N2 1.337(4) . ?
C17 N2 1.332(4) . ?
C17 C18 1.389(4) . ?
C19 N3 1.341(3) . ?
C19 C20 1.388(4) . ?
C20 C21 1.381(4) . ?
C21 C22 1.388(4) . ?
C22 C23 1.384(4) . ?
C23 N3 1.335(3) . ?
C24 C29 1.385(3) . ?
C24 C25 1.392(3) . ?
C24 I1 2.093(2) . ?
C25 F1 1.348(3) . ?
C25 C26 1.384(3) . ?
C26 F2 1.344(3) . ?
C26 C27 1.385(3) . ?
C27 C28 1.384(3) . ?
C27 I2 2.111(2) . ?
C28 F3 1.349(3) . ?
C28 C29 1.381(3) . ?
C29 F4 1.346(3) . ?
N1 I2 2.793(2) 4.465 ?
N2 I1 2.845(2) 4.666 ?

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 Cu1 O2 92.37(7) . . ?
O1 Cu1 O3 164.84(9) . . ?
O1 Cu1 O4 86.98(7) . . ?
O1 Cu1 N3 99.17(8) . . ?
O2 Cu1 O3 86.87(7) . . ?
O2 Cu1 O4 174.51(8) . . ?
O2 Cu1 N3 90.73(8) . . ?
O3 Cu1 O4 92.33(7) . . ?
O3 Cu1 N3 95.98(8) . . ?
O4 Cu1 N3 94.75(8) . . ?
O1 C2 C3 125.3(2) . . ?
O1 C2 C1 116.7(2) . . ?
C3 C2 C1 117.9(2) . . ?
C4 C3 C2 125.0(2) . . ?
O2 C4 C3 125.2(2) . . ?
O2 C4 C5 115.8(2) . . ?
C3 C4 C5 118.9(2) . . ?
C6 C5 C9 117.4(2) . . ?
C6 C5 C4 119.4(2) . . ?
C9 C5 C4 123.2(2) . . ?
C7 C6 C5 119.3(2) . . ?
N1 C7 C6 123.6(3) . . ?
N1 C8 C9 124.2(2) . . ?
C8 C9 C5 118.7(2) . . ?
O3 C11 C12 125.3(2) . . ?
O3 C11 C10 116.3(2) . . ?
C12 C11 C10 118.4(2) . . ?
C13 C12 C11 124.9(2) . . ?
O4 C13 C12 125.1(2) . . ?
O4 C13 C14 115.9(2) . . ?
C12 C13 C14 119.0(2) . . ?
C15 C14 C18 116.7(2) . . ?
C15 C14 C13 119.9(2) . . ?
C18 C14 C13 123.4(2) . . ?
C14 C15 C16 119.6(3) . . ?
N2 C16 C15 123.4(3) . . ?
N2 C17 C18 123.6(3) . . ?
C17 C18 C14 119.8(2) . . ?
N3 C19 C20 123.0(2) . . ?
C21 C20 C19 118.8(3) . . ?
C20 C21 C22 118.6(3) . . ?
C23 C22 C21 118.9(3) . . ?
N3 C23 C22 123.0(2) . . ?
C8 N1 C7 116.8(2) . . ?
C17 N2 C16 116.8(2) . . ?
C23 N3 C19 117.7(2) . . ?
C23 N3 Cu1 121.47(18) . . ?
C19 N3 Cu1 120.79(18) . . ?
C2 O1 Cu1 125.63(16) . . ?
C4 O2 Cu1 124.69(16) . . ?
C11 O3 Cu1 125.62(16) . . ?
C13 O4 Cu1 125.20(16) . . ?
C29 C24 C25 116.4(2) . . ?
C29 C24 I1 121.70(18) . . ?
C25 C24 I1 121.89(18) . . ?
F1 C25 C26 117.8(2) . . ?
F1 C25 C24 120.1(2) . . ?
C26 C25 C24 122.1(2) . . ?
F2 C26 C25 118.6(2) . . ?
F2 C26 C27 120.5(2) . . ?
C25 C26 C27 120.9(2) . . ?
C28 C27 C26 117.3(2) . . ?
C28 C27 I2 121.90(18) . . ?
C26 C27 I2 120.81(18) . . ?
F3 C28 C29 118.1(2) . . ?
F3 C28 C27 120.3(2) . . ?
C29 C28 C27 121.7(2) . . ?
F4 C29 C28 118.0(2) . . ?
F4 C29 C24 120.3(2) . . ?
C28 C29 C24 121.7(2) . . ?
C7 N1 I2 122.57(17) . 4.465 ?
C8 N1 I2 120.60(18) . 4.465 ?
N1 I2 C27 178.26(9) 4.666 . ?
C16 N2 I1 123.8(2) . 4.666 ?
C17 N2 I1 119.15(18) . 4.666 ?
N2 I1 C24 179.18(8) 4.465 . ?

_refine_diff_density_max         0.867
_refine_diff_density_min         -0.904
_refine_diff_density_rms         0.099



