# Supplementary Information (SI) for Dalton Transactions.
# This journal is © The Royal Society of Chemistry 2025

####################################################################### 
# 
# 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_1a
_database_code_depnum_ccdc_archive 'CCDC 2468989'
loop_
_audit_author_name
_audit_author_address
'Tiago Cruz'
;Centro de Quimica Estrutural, Departamento de Engenharia Quimica, Instituto Superior Tecnico
Portugal
;
_audit_update_record             
;
2025-08-12 deposited with the CCDC.	2025-08-13 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2019/3
_shelx_SHELXL_version_number     2019/3
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_formula_moiety         'C14 H20 Cl Cu N4'
_chemical_formula_sum            'C14 H20 Cl Cu N4'
_chemical_melting_point          ?

_exptl_crystal_description       prism
_exptl_crystal_colour            white
_diffrn_ambient_temperature      150
_chemical_formula_weight         343.33

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'
Cl Cl 0.1484 0.1585 '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'

_space_group_crystal_system      monoclinic
_space_group_IT_number           9
_space_group_name_H-M_alt        'C c'
_space_group_name_Hall           'C -2yc'
_chemical_absolute_configuration ?

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'

_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.
;

_cell_length_a                   9.393(3)
_cell_length_b                   25.453(9)
_cell_length_c                   7.699(2)
_cell_angle_alpha                90
_cell_angle_beta                 119.745(8)
_cell_angle_gamma                90
_cell_volume                     1598.2(9)
_cell_formula_units_Z            4
_cell_measurement_temperature    150
_cell_measurement_reflns_used    1362
_cell_measurement_theta_min      2.62
_cell_measurement_theta_max      23.14
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.427
_exptl_crystal_F_000             712
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.400
_exptl_crystal_size_mid          0.100
_exptl_crystal_size_min          0.040
_exptl_absorpt_coefficient_mu    1.529
_shelx_estimated_absorpt_T_min   0.580
_shelx_estimated_absorpt_T_max   0.941
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.580
_exptl_absorpt_correction_T_max  0.941
_exptl_absorpt_process_details   'SADABS (Sheldrick, 1996)'
_exptl_absorpt_special_details   ?
_diffrn_radiation_probe          ?
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_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            4537
_diffrn_reflns_av_unetI/netI     0.0815
_diffrn_reflns_av_R_equivalents  0.0340
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -31
_diffrn_reflns_limit_k_max       27
_diffrn_reflns_limit_l_min       -9
_diffrn_reflns_limit_l_max       8
_diffrn_reflns_theta_min         2.622
_diffrn_reflns_theta_max         26.444
_diffrn_reflns_theta_full        26.444
_diffrn_measured_fraction_theta_max 0.990
_diffrn_measured_fraction_theta_full 0.990
_diffrn_reflns_Laue_measured_fraction_max 0.990
_diffrn_reflns_Laue_measured_fraction_full 0.990
_diffrn_reflns_point_group_measured_fraction_max 0.840
_diffrn_reflns_point_group_measured_fraction_full 0.840
_reflns_number_total             2764
_reflns_number_gt                2207
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.689
_reflns_Friedel_fraction_max     0.689
_reflns_Friedel_fraction_full    0.689

_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. Completness statistics refer to single and
 composite reflections containing twin component 1 only.
;

_computing_data_collection       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXL-2019/2 (Sheldrick, 2019)'
_computing_structure_refinement  'SHELXL-2019/2 (Sheldrick, 2019)'
_computing_molecular_graphics    enCIFer
_computing_publication_material  Mercury
_refine_special_details          
;
 Refined as a 2-component inversion twin.
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     'w=1/[σ²(Fo²)] 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_abs_structure_details 
;
 Refined as an inversion twin.
;
_refine_ls_abs_structure_Flack   0.039(18)
_refine_ls_number_reflns         2764
_refine_ls_number_parameters     186
_refine_ls_number_restraints     2
_refine_ls_R_factor_all          0.0512
_refine_ls_R_factor_gt           0.0352
_refine_ls_wR_factor_ref         0.0575
_refine_ls_wR_factor_gt          0.0541
_refine_ls_goodness_of_fit_ref   0.889
_refine_ls_restrained_S_all      0.889
_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
Cu1 Cu 0.30930(7) 0.60059(3) 0.38628(8) 0.02846(18) Uani 1 1 d . . . . .
Cl1 Cl 0.05002(15) 0.61744(6) 0.22745(18) 0.0342(4) Uani 1 1 d . . . . .
N4 N 0.6199(4) 0.55156(16) 0.6904(5) 0.0207(10) Uani 1 1 d . . . . .
N1 N 0.4997(4) 0.64263(16) 0.4031(5) 0.0217(10) Uani 1 1 d . . . . .
N3 N 0.4561(4) 0.54273(16) 0.5610(6) 0.0242(11) Uani 1 1 d . . . . .
C14 C 0.5826(8) 0.7349(3) 0.7874(9) 0.0524(18) Uani 1 1 d . . . . .
H14A H 0.470441 0.731516 0.701125 0.063 Uiso 1 1 calc R U . . .
H14B H 0.630906 0.767997 0.816535 0.063 Uiso 1 1 calc R U . . .
N2 N 0.6578(4) 0.63076(17) 0.5484(5) 0.0199(10) Uani 1 1 d . . . . .
C7 C 0.5880(5) 0.4661(2) 0.6812(7) 0.0229(12) Uani 1 1 d . . . . .
H7 H 0.607056 0.430241 0.703771 0.027 Uiso 1 1 calc R U . . .
C9 C 0.8813(6) 0.5026(2) 0.9143(7) 0.0289(15) Uani 1 1 d . . . . .
H9A H 0.940958 0.523775 0.868927 0.043 Uiso 1 1 calc R U . . .
H9B H 0.917175 0.466768 0.927386 0.043 Uiso 1 1 calc R U . . .
H9C H 0.900784 0.515274 1.041739 0.043 Uiso 1 1 calc R U . . .
C6 C 0.4372(6) 0.4908(2) 0.5538(7) 0.0230(12) Uani 1 1 d . . . . .
C1 C 0.5178(6) 0.6724(2) 0.2730(7) 0.0234(13) Uani 1 1 d . . . . .
C13 C 0.6727(7) 0.6930(2) 0.8680(7) 0.0289(14) Uani 1 1 d . . . . .
H13 H 0.784402 0.697956 0.953536 0.035 Uiso 1 1 calc R U . . .
C12 C 0.6092(6) 0.6379(2) 0.8327(7) 0.0253(13) Uani 1 1 d . . . . .
H12A H 0.490799 0.638347 0.749711 0.030 Uiso 1 1 calc R U . . .
H12B H 0.636046 0.621829 0.959637 0.030 Uiso 1 1 calc R U . . .
C5 C 0.3669(6) 0.6923(2) 0.0864(7) 0.0359(15) Uani 1 1 d . . . . .
H5A H 0.352642 0.672622 -0.027645 0.054 Uiso 1 1 calc R U . . .
H5B H 0.380550 0.728797 0.067335 0.054 Uiso 1 1 calc R U . . .
H5C H 0.272073 0.687876 0.101442 0.054 Uiso 1 1 calc R U . . .
C2 C 0.6846(7) 0.6801(2) 0.3326(7) 0.0247(13) Uani 1 1 d . . . . .
H2 H 0.727485 0.699132 0.265942 0.030 Uiso 1 1 calc R U . . .
C4 C 0.9517(5) 0.6490(2) 0.6471(7) 0.0331(15) Uani 1 1 d . . . . .
H4A H 0.982914 0.668543 0.767414 0.050 Uiso 1 1 calc R U . . .
H4B H 1.007154 0.663036 0.580914 0.050 Uiso 1 1 calc R U . . .
H4C H 0.981428 0.612797 0.679941 0.050 Uiso 1 1 calc R U . . .
C11 C 0.6822(5) 0.60515(19) 0.7310(6) 0.0205(12) Uani 1 1 d . . . . .
H11 H 0.800729 0.603154 0.822813 0.025 Uiso 1 1 calc R U . . .
C3 C 0.7709(5) 0.6532(2) 0.5120(7) 0.0227(12) Uani 1 1 d . . . . .
C10 C 0.2748(6) 0.4657(2) 0.4205(8) 0.0373(16) Uani 1 1 d . . . . .
H10A H 0.193576 0.492440 0.353650 0.056 Uiso 1 1 calc R U . . .
H10B H 0.244118 0.444260 0.499242 0.056 Uiso 1 1 calc R U . . .
H10C H 0.282572 0.444202 0.323015 0.056 Uiso 1 1 calc R U . . .
C8 C 0.7005(6) 0.5057(2) 0.7650(7) 0.0215(13) 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 N3 2.010(4) . ?
Cu1 N1 2.032(4) . ?
Cu1 Cl1 2.1577(15) . ?
N4 C8 1.355(6) . ?
N4 N3 1.375(5) . ?
N4 C11 1.456(6) . ?
N1 C1 1.333(6) . ?
N1 N2 1.378(5) . ?
N3 C6 1.331(6) . ?
C14 C13 1.309(7) . ?
C14 H14A 0.9300 . ?
C14 H14B 0.9300 . ?
N2 C3 1.352(6) . ?
N2 C11 1.460(6) . ?
C7 C8 1.368(7) . ?
C7 C6 1.409(6) . ?
C7 H7 0.9300 . ?
C9 C8 1.508(6) . ?
C9 H9A 0.9600 . ?
C9 H9B 0.9600 . ?
C9 H9C 0.9600 . ?
C6 C10 1.495(6) . ?
C1 C2 1.411(7) . ?
C1 C5 1.519(6) . ?
C13 C12 1.497(7) . ?
C13 H13 0.9300 . ?
C12 C11 1.520(7) . ?
C12 H12A 0.9700 . ?
C12 H12B 0.9700 . ?
C5 H5A 0.9600 . ?
C5 H5B 0.9600 . ?
C5 H5C 0.9600 . ?
C2 C3 1.387(7) . ?
C2 H2 0.9300 . ?
C4 C3 1.492(6) . ?
C4 H4A 0.9600 . ?
C4 H4B 0.9600 . ?
C4 H4C 0.9600 . ?
C11 H11 0.9800 . ?
C10 H10A 0.9600 . ?
C10 H10B 0.9600 . ?
C10 H10C 0.9600 . ?

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
N3 Cu1 N1 93.06(16) . . ?
N3 Cu1 Cl1 137.02(12) . . ?
N1 Cu1 Cl1 129.91(12) . . ?
C8 N4 N3 110.8(4) . . ?
C8 N4 C11 129.5(4) . . ?
N3 N4 C11 119.7(4) . . ?
C1 N1 N2 104.3(4) . . ?
C1 N1 Cu1 133.5(3) . . ?
N2 N1 Cu1 119.7(3) . . ?
C6 N3 N4 105.7(4) . . ?
C6 N3 Cu1 131.8(3) . . ?
N4 N3 Cu1 121.0(3) . . ?
C13 C14 H14A 120.0 . . ?
C13 C14 H14B 120.0 . . ?
H14A C14 H14B 120.0 . . ?
C3 N2 N1 112.4(4) . . ?
C3 N2 C11 128.5(4) . . ?
N1 N2 C11 118.1(4) . . ?
C8 C7 C6 105.9(5) . . ?
C8 C7 H7 127.0 . . ?
C6 C7 H7 127.0 . . ?
C8 C9 H9A 109.5 . . ?
C8 C9 H9B 109.5 . . ?
H9A C9 H9B 109.5 . . ?
C8 C9 H9C 109.5 . . ?
H9A C9 H9C 109.5 . . ?
H9B C9 H9C 109.5 . . ?
N3 C6 C7 110.3(4) . . ?
N3 C6 C10 121.5(4) . . ?
C7 C6 C10 128.1(5) . . ?
N1 C1 C2 111.7(4) . . ?
N1 C1 C5 119.5(5) . . ?
C2 C1 C5 128.8(5) . . ?
C14 C13 C12 124.9(5) . . ?
C14 C13 H13 117.6 . . ?
C12 C13 H13 117.6 . . ?
C13 C12 C11 111.5(4) . . ?
C13 C12 H12A 109.3 . . ?
C11 C12 H12A 109.3 . . ?
C13 C12 H12B 109.3 . . ?
C11 C12 H12B 109.3 . . ?
H12A C12 H12B 108.0 . . ?
C1 C5 H5A 109.5 . . ?
C1 C5 H5B 109.5 . . ?
H5A C5 H5B 109.5 . . ?
C1 C5 H5C 109.5 . . ?
H5A C5 H5C 109.5 . . ?
H5B C5 H5C 109.5 . . ?
C3 C2 C1 105.2(5) . . ?
C3 C2 H2 127.4 . . ?
C1 C2 H2 127.4 . . ?
C3 C4 H4A 109.5 . . ?
C3 C4 H4B 109.5 . . ?
H4A C4 H4B 109.5 . . ?
C3 C4 H4C 109.5 . . ?
H4A C4 H4C 109.5 . . ?
H4B C4 H4C 109.5 . . ?
N4 C11 N2 110.9(4) . . ?
N4 C11 C12 112.8(4) . . ?
N2 C11 C12 110.8(4) . . ?
N4 C11 H11 107.3 . . ?
N2 C11 H11 107.3 . . ?
C12 C11 H11 107.3 . . ?
N2 C3 C2 106.5(4) . . ?
N2 C3 C4 124.4(4) . . ?
C2 C3 C4 129.1(5) . . ?
C6 C10 H10A 109.5 . . ?
C6 C10 H10B 109.5 . . ?
H10A C10 H10B 109.5 . . ?
C6 C10 H10C 109.5 . . ?
H10A C10 H10C 109.5 . . ?
H10B C10 H10C 109.5 . . ?
N4 C8 C7 107.2(4) . . ?
N4 C8 C9 123.3(5) . . ?
C7 C8 C9 129.5(5) . . ?

_refine_diff_density_max         0.278
_refine_diff_density_min         -0.304
_refine_diff_density_rms         0.064


####################################################################### 
# 
# 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_3a
_database_code_depnum_ccdc_archive 'CCDC 2468991'
loop_
_audit_author_name
_audit_author_address
'Tiago Cruz'
;Centro de Quimica Estrutural, Departamento de Engenharia Quimica, Instituto Superior Tecnico
Portugal
;
_audit_update_record             
;
2025-08-12 deposited with the CCDC.	2025-08-13 downloaded from the CCDC.
;
# start Validation Reply Form
_vrf_SHFSU01_3a                  
;
PROBLEM: The absolute value of parameter shift to su ratio > 0.20
RESPONSE: The analyzed crystal presented poor quality.
;
_vrf_PLAT080_3a                  
;
PROBLEM: Maximum Shift/Error ............................       2.55 Why ?
RESPONSE: The analyzed crystal presented poor quality.
;
_vrf_PLAT213_3a                  
;
PROBLEM: Atom C22             has ADP max/min Ratio .....        9.1 prolat
RESPONSE: The analyzed crystal presented poor quality.
;
_vrf_PLAT241_3a                  
;
PROBLEM: High   'MainMol' Ueq as Compared to Neighbors of        C22 Check
RESPONSE: The analyzed crystal presented poor quality.
;
_vrf_PLAT242_3a                  
;
PROBLEM: Low    'MainMol' Ueq as Compared to Neighbors of        C21 Check
RESPONSE: The analyzed crystal presented poor quality.
;
_vrf_PLAT413_3a                  
;
PROBLEM: Short Inter XH3 .. XHn     H21      ..H23A     .       0.90 Ang.
RESPONSE: The analyzed crystal presented poor quality.
;
# Added during the CSD deposition process: Tuesday 12 August 2025 10:15 AM
# end Validation Reply Form


_audit_creation_method           SHELXL-2019/3
_shelx_SHELXL_version_number     2019/3
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_formula_moiety         'C28 H40 B Cu F4 N8'
_chemical_formula_sum            'C28 H40 B Cu F4 N8'
_chemical_melting_point          ?

_exptl_crystal_description       prism
_exptl_crystal_colour            white
_diffrn_ambient_temperature      150
_chemical_formula_weight         639.03

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'
B B 0.0013 0.0007 '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'
F F 0.0171 0.0103 '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'

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

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

_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.
;

_cell_length_a                   8.226(11)
_cell_length_b                   13.824(17)
_cell_length_c                   14.502(18)
_cell_angle_alpha                100.60(3)
_cell_angle_beta                 96.12(4)
_cell_angle_gamma                97.88(3)
_cell_volume                     1591(3)
_cell_formula_units_Z            2
_cell_measurement_temperature    150
_cell_measurement_reflns_used    2686
_cell_measurement_theta_min      2.30
_cell_measurement_theta_max      23.47
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.334
_exptl_crystal_F_000             668
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.10
_exptl_crystal_size_mid          0.02
_exptl_crystal_size_min          0.02
_exptl_absorpt_coefficient_mu    0.741
_shelx_estimated_absorpt_T_min   0.930
_shelx_estimated_absorpt_T_max   0.985
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.93
_exptl_absorpt_correction_T_max  0.985
_exptl_absorpt_process_details   ?
_exptl_absorpt_special_details   ?
_diffrn_radiation_probe          ?
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_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            12173
_diffrn_reflns_av_unetI/netI     0.0843
_diffrn_reflns_av_R_equivalents  0.0482
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_theta_min         1.442
_diffrn_reflns_theta_max         26.768
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.977
_diffrn_measured_fraction_theta_full 0.991
_diffrn_reflns_Laue_measured_fraction_max 0.977
_diffrn_reflns_Laue_measured_fraction_full 0.991
_diffrn_reflns_point_group_measured_fraction_max 0.977
_diffrn_reflns_point_group_measured_fraction_full 0.991
_reflns_number_total             6633
_reflns_number_gt                4187
_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'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2019/2 (Sheldrick, 2019)'
_computing_molecular_graphics    enCIFer
_computing_publication_material  Mercury
_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)+(0.2000P)²] 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         6633
_refine_ls_number_parameters     387
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1566
_refine_ls_R_factor_gt           0.1131
_refine_ls_wR_factor_ref         0.3615
_refine_ls_wR_factor_gt          0.3228
_refine_ls_goodness_of_fit_ref   1.272
_refine_ls_restrained_S_all      1.272
_refine_ls_shift/su_max          2.554
_refine_ls_shift/su_mean         0.140

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 0.46622(10) 0.79082(5) 0.27517(6) 0.0454(4) Uani 1 1 d . . . . .
N2 N 0.4716(6) 0.9955(4) 0.2364(4) 0.0369(11) Uani 1 1 d . . . . .
N4 N 0.6954(6) 0.9170(4) 0.1771(4) 0.0385(12) Uani 1 1 d . . . . .
N1 N 0.3898(6) 0.9215(4) 0.2741(4) 0.0475(14) Uani 1 1 d . . . . .
N3 N 0.6833(7) 0.8298(4) 0.2094(4) 0.0450(13) Uani 1 1 d . . . . .
N5 N 0.5130(7) 0.6891(4) 0.3526(4) 0.0472(14) Uani 1 1 d . . . . .
N6 N 0.4509(9) 0.5901(4) 0.3203(5) 0.0645(19) Uani 1 1 d . . . . .
N7 N 0.3100(9) 0.6852(5) 0.1640(5) 0.071(2) Uani 1 1 d . . . . .
C3 C 0.3752(8) 1.0643(5) 0.2211(5) 0.0419(14) Uani 1 1 d . . . . .
C11 C 0.6521(7) 1.0052(4) 0.2359(5) 0.0385(14) Uani 1 1 d . . . . .
H11 H 0.685898 1.062419 0.207283 0.046 Uiso 1 1 calc R U . . .
C12 C 0.7454(8) 1.0265(5) 0.3358(5) 0.0462(16) Uani 1 1 d . . . . .
H12A H 0.716597 0.969968 0.365174 0.055 Uiso 1 1 calc R U . . .
H12B H 0.863523 1.034252 0.332430 0.055 Uiso 1 1 calc R U . . .
C8 C 0.7662(8) 0.9120(5) 0.0963(5) 0.0442(15) Uani 1 1 d . . . . .
C13 C 0.7071(9) 1.1181(6) 0.3959(6) 0.0564(18) Uani 1 1 d . . . . .
H13 H 0.743852 1.178002 0.378428 0.068 Uiso 1 1 calc R U . . .
C4 C 0.4321(9) 1.1543(5) 0.1828(6) 0.0532(18) Uani 1 1 d . . . . .
H4A H 0.509948 1.200591 0.230082 0.080 Uiso 1 1 calc R U . . .
H4B H 0.338682 1.185283 0.166104 0.080 Uiso 1 1 calc R U . . .
H4C H 0.484311 1.134966 0.127691 0.080 Uiso 1 1 calc R U . . .
C2 C 0.2242(9) 1.0323(6) 0.2479(6) 0.059(2) Uani 1 1 d . . . . .
H2 H 0.130108 1.062581 0.244440 0.071 Uiso 1 1 calc R U . . .
C9 C 0.7907(10) 0.9986(6) 0.0469(5) 0.0558(19) Uani 1 1 d . . . . .
H9A H 0.686811 1.021071 0.034258 0.084 Uiso 1 1 calc R U . . .
H9B H 0.832467 0.977862 -0.011741 0.084 Uiso 1 1 calc R U . . .
H9C H 0.868626 1.051964 0.086524 0.084 Uiso 1 1 calc R U . . .
C6 C 0.7505(11) 0.7687(6) 0.1482(6) 0.063(2) Uani 1 1 d . . . . .
C1 C 0.2412(8) 0.9463(6) 0.2808(6) 0.058(2) Uani 1 1 d . . . . .
C7 C 0.8043(11) 0.8181(6) 0.0762(5) 0.061(2) Uani 1 1 d . . . . .
H7 H 0.855506 0.791433 0.025353 0.073 Uiso 1 1 calc R U . . .
C27 C 0.1369(9) 0.5638(6) 0.4052(7) 0.063(2) Uani 1 1 d . . . . .
H27 H 0.134659 0.496411 0.405536 0.076 Uiso 1 1 calc R U . . .
C19 C 0.7512(9) 0.7892(6) 0.4634(6) 0.065(2) Uani 1 1 d . . . . .
H19A H 0.836482 0.806291 0.426186 0.097 Uiso 1 1 calc R U . . .
H19B H 0.801009 0.782757 0.524507 0.097 Uiso 1 1 calc R U . . .
H19C H 0.683372 0.840556 0.470979 0.097 Uiso 1 1 calc R U . . .
C15 C 0.6475(8) 0.6932(6) 0.4149(6) 0.055(2) Uani 1 1 d . . . . .
C26 C 0.1511(10) 0.5948(6) 0.3136(7) 0.072(3) Uani 1 1 d . . . . .
H26A H 0.167009 0.666992 0.324523 0.087 Uiso 1 1 calc R U . . .
H26B H 0.047462 0.569901 0.272152 0.087 Uiso 1 1 calc R U . . .
C14 C 0.6304(12) 1.1247(7) 0.4680(7) 0.088(3) Uani 1 1 d . . . . .
H14A H 0.590576 1.067417 0.488935 0.106 Uiso 1 1 calc R U . . .
H14B H 0.614172 1.186758 0.499723 0.106 Uiso 1 1 calc R U . . .
C28 C 0.1273(10) 0.6205(7) 0.4835(9) 0.083(3) Uani 1 1 d . . . . .
H28A H 0.129056 0.688430 0.486590 0.099 Uiso 1 1 calc R U . . .
H28B H 0.118648 0.594015 0.537544 0.099 Uiso 1 1 calc R U . . .
C5 C 0.1124(10) 0.8818(8) 0.3194(9) 0.093(4) Uani 1 1 d . . . . .
H5A H 0.074537 0.921408 0.371982 0.140 Uiso 1 1 calc R U . . .
H5B H 0.160187 0.828555 0.340046 0.140 Uiso 1 1 calc R U . . .
H5C H 0.020490 0.854455 0.270751 0.140 Uiso 1 1 calc R U . . .
C25 C 0.2894(14) 0.5594(6) 0.2637(6) 0.076(3) Uani 1 1 d . . . . .
H25 H 0.267846 0.486353 0.251449 0.092 Uiso 1 1 calc R U . . .
N8 N 0.2884(18) 0.5879(6) 0.1719(6) 0.144(6) Uani 1 1 d . . . . .
C17 C 0.5490(13) 0.5331(7) 0.3642(10) 0.097(4) Uani 1 1 d . . . . .
C16 C 0.6697(11) 0.5959(7) 0.4214(10) 0.098(4) Uani 1 1 d . . . . .
H16 H 0.754693 0.578433 0.459464 0.118 Uiso 1 1 calc R U . . .
C10 C 0.7631(16) 0.6666(6) 0.1616(7) 0.087(3) Uani 1 1 d . . . . .
H10A H 0.778891 0.666125 0.228040 0.130 Uiso 1 1 calc R U . . .
H10B H 0.855582 0.644717 0.133355 0.130 Uiso 1 1 calc R U . . .
H10C H 0.663177 0.622603 0.132063 0.130 Uiso 1 1 calc R U . . .
B1 B -0.0134(10) 0.2734(6) 0.2318(6) 0.0513(19) Uani 1 1 d . . . . .
C18 C 0.5079(17) 0.4183(8) 0.3396(16) 0.178(9) Uani 1 1 d . . . . .
H18A H 0.570763 0.391019 0.385290 0.267 Uiso 1 1 calc R U . . .
H18B H 0.535541 0.394428 0.277645 0.267 Uiso 1 1 calc R U . . .
H18C H 0.391781 0.397907 0.340383 0.267 Uiso 1 1 calc R U . . .
F1 F 0.0554(11) 0.2452(7) 0.1513(5) 0.144(3) Uani 1 1 d . . . . .
F2 F 0.0963(13) 0.3049(11) 0.3024(7) 0.254(8) Uani 1 1 d . . . . .
F3 F -0.1081(19) 0.3436(9) 0.2285(9) 0.236(7) Uani 1 1 d . . . . .
F4 F -0.111(2) 0.2042(8) 0.2345(11) 0.317(11) Uani 1 1 d . . . . .
C24 C 0.3015(15) 0.7849(8) 0.0410(7) 0.114(5) Uani 1 1 d . . . . .
H24A H 0.254016 0.832825 0.082008 0.171 Uiso 1 1 calc R U . . .
H24B H 0.244138 0.773845 -0.022200 0.171 Uiso 1 1 calc R U . . .
H24C H 0.416438 0.809706 0.040999 0.171 Uiso 1 1 calc R U . . .
C20 C 0.286(2) 0.6894(9) 0.0751(7) 0.170(9) Uani 1 1 d . . . . .
C22 C 0.226(6) 0.5343(11) 0.0880(10) 0.51(3) Uani 1 1 d . . . . .
C21 C 0.167(2) 0.6085(8) 0.0258(10) 0.144(6) Uani 1 1 d . . . . .
H21 H 0.083311 0.601381 -0.024711 0.172 Uiso 1 1 calc R U . . .
C23 C 0.129(5) 0.4328(11) 0.0739(15) 0.39(2) Uani 1 1 d . . . . .
H23A H 0.020288 0.431967 0.042516 0.586 Uiso 1 1 calc R U . . .
H23B H 0.121730 0.414610 0.134202 0.586 Uiso 1 1 calc R U . . .
H23C H 0.183738 0.386145 0.035743 0.586 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
Cu1 N5 2.006(6) . ?
Cu1 N1 1.995(6) . ?
Cu1 N7 2.136(7) . ?
Cu1 N3 2.162(6) . ?
N2 C3 1.353(8) . ?
N2 N1 1.375(6) . ?
N2 C11 1.473(8) . ?
N4 N3 1.367(7) . ?
N4 C8 1.357(8) . ?
N4 C11 1.464(8) . ?
N1 C1 1.323(9) . ?
N3 C6 1.328(10) . ?
N5 C15 1.340(9) . ?
N5 N6 1.369(8) . ?
N6 C25 1.450(13) . ?
N6 C17 1.388(12) . ?
N7 C20 1.296(11) . ?
N7 N8 1.359(10) . ?
C3 C2 1.380(9) . ?
C3 C4 1.492(9) . ?
C11 C12 1.522(9) . ?
C11 H11 0.9800 . ?
C12 C13 1.492(10) . ?
C12 H12A 0.9700 . ?
C12 H12B 0.9700 . ?
C8 C7 1.365(10) . ?
C8 C9 1.506(9) . ?
C13 C14 1.274(11) . ?
C13 H13 0.9300 . ?
C4 H4A 0.9600 . ?
C4 H4B 0.9600 . ?
C4 H4C 0.9600 . ?
C2 C1 1.378(9) . ?
C2 H2 0.9300 . ?
C9 H9A 0.9600 . ?
C9 H9B 0.9600 . ?
C9 H9C 0.9600 . ?
C6 C7 1.425(10) . ?
C6 C10 1.475(11) . ?
C1 C5 1.511(9) . ?
C7 H7 0.9300 . ?
C27 C28 1.272(13) . ?
C27 C26 1.480(11) . ?
C27 H27 0.9300 . ?
C19 C15 1.483(11) . ?
C19 H19A 0.9600 . ?
C19 H19B 0.9600 . ?
C19 H19C 0.9600 . ?
C15 C16 1.401(10) . ?
C26 C25 1.501(14) . ?
C26 H26A 0.9700 . ?
C26 H26B 0.9700 . ?
C14 H14A 0.9300 . ?
C14 H14B 0.9300 . ?
C28 H28A 0.9300 . ?
C28 H28B 0.9300 . ?
C5 H5A 0.9600 . ?
C5 H5B 0.9600 . ?
C5 H5C 0.9600 . ?
C25 N8 1.457(11) . ?
C25 H25 0.9800 . ?
N8 C22 1.312(18) . ?
C17 C16 1.323(17) . ?
C17 C18 1.543(13) . ?
C16 H16 0.9300 . ?
C10 H10A 0.9600 . ?
C10 H10B 0.9600 . ?
C10 H10C 0.9600 . ?
B1 F4 1.169(10) . ?
B1 F2 1.258(12) . ?
B1 F3 1.329(12) . ?
B1 F1 1.367(11) . ?
C18 H18A 0.9600 . ?
C18 H18B 0.9600 . ?
C18 H18C 0.9600 . ?
C24 C20 1.487(13) . ?
C24 H24A 0.9600 . ?
C24 H24B 0.9600 . ?
C24 H24C 0.9600 . ?
C20 C21 1.408(16) . ?
C22 C21 1.58(3) . ?
C22 C23 1.48(2) . ?
C21 H21 0.9300 . ?
C23 H23A 0.9977 . ?
C23 H23B 1.0110 . ?
C23 H23C 0.9836 . ?

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
N5 Cu1 N1 146.1(2) . . ?
N5 Cu1 N7 94.2(3) . . ?
N1 Cu1 N7 106.2(3) . . ?
N5 Cu1 N3 108.2(2) . . ?
N1 Cu1 N3 93.6(2) . . ?
N7 Cu1 N3 102.6(3) . . ?
C3 N2 N1 111.8(5) . . ?
C3 N2 C11 126.5(5) . . ?
N1 N2 C11 120.3(5) . . ?
N3 N4 C8 113.0(5) . . ?
N3 N4 C11 118.9(5) . . ?
C8 N4 C11 127.7(5) . . ?
C1 N1 N2 104.3(5) . . ?
C1 N1 Cu1 129.9(4) . . ?
N2 N1 Cu1 123.2(4) . . ?
N4 N3 C6 104.9(5) . . ?
N4 N3 Cu1 116.7(4) . . ?
C6 N3 Cu1 126.5(5) . . ?
C15 N5 N6 106.4(6) . . ?
C15 N5 Cu1 127.1(4) . . ?
N6 N5 Cu1 121.1(5) . . ?
N5 N6 C25 120.6(7) . . ?
N5 N6 C17 109.4(8) . . ?
C25 N6 C17 128.9(7) . . ?
C20 N7 N8 108.8(8) . . ?
C20 N7 Cu1 127.3(5) . . ?
N8 N7 Cu1 117.8(6) . . ?
N2 C3 C2 105.9(5) . . ?
N2 C3 C4 123.7(6) . . ?
C2 C3 C4 130.4(6) . . ?
N2 C11 N4 110.8(5) . . ?
N2 C11 C12 111.8(5) . . ?
N4 C11 C12 111.6(5) . . ?
N2 C11 H11 107.5 . . ?
N4 C11 H11 107.4 . . ?
C12 C11 H11 107.5 . . ?
C13 C12 C11 112.3(6) . . ?
C13 C12 H12A 109.2 . . ?
C11 C12 H12A 109.2 . . ?
C13 C12 H12B 109.1 . . ?
C11 C12 H12B 109.1 . . ?
H12A C12 H12B 107.9 . . ?
C7 C8 N4 105.5(6) . . ?
C7 C8 C9 131.9(6) . . ?
N4 C8 C9 122.6(6) . . ?
C14 C13 C12 128.2(8) . . ?
C14 C13 H13 115.8 . . ?
C12 C13 H13 116.0 . . ?
C3 C4 H4A 109.4 . . ?
C3 C4 H4B 109.5 . . ?
H4A C4 H4B 109.5 . . ?
C3 C4 H4C 109.5 . . ?
H4A C4 H4C 109.5 . . ?
H4B C4 H4C 109.5 . . ?
C1 C2 C3 106.0(6) . . ?
C1 C2 H2 127.0 . . ?
C3 C2 H2 127.0 . . ?
C8 C9 H9A 109.5 . . ?
C8 C9 H9B 109.5 . . ?
H9A C9 H9B 109.5 . . ?
C8 C9 H9C 109.5 . . ?
H9A C9 H9C 109.5 . . ?
H9B C9 H9C 109.5 . . ?
N3 C6 C7 110.0(7) . . ?
N3 C6 C10 120.5(7) . . ?
C7 C6 C10 129.5(8) . . ?
N1 C1 C2 112.1(6) . . ?
N1 C1 C5 120.3(6) . . ?
C2 C1 C5 127.6(7) . . ?
C8 C7 C6 106.6(6) . . ?
C8 C7 H7 126.7 . . ?
C6 C7 H7 126.7 . . ?
C28 C27 C26 126.2(8) . . ?
C28 C27 H27 116.8 . . ?
C26 C27 H27 116.9 . . ?
C15 C19 H19A 109.5 . . ?
C15 C19 H19B 109.4 . . ?
H19A C19 H19B 109.5 . . ?
C15 C19 H19C 109.5 . . ?
H19A C19 H19C 109.5 . . ?
H19B C19 H19C 109.5 . . ?
N5 C15 C16 108.8(8) . . ?
N5 C15 C19 122.1(6) . . ?
C16 C15 C19 129.1(8) . . ?
C27 C26 C25 114.8(7) . . ?
C27 C26 H26A 108.6 . . ?
C25 C26 H26A 108.6 . . ?
C27 C26 H26B 108.6 . . ?
C25 C26 H26B 108.5 . . ?
H26A C26 H26B 107.6 . . ?
C13 C14 H14A 119.9 . . ?
C13 C14 H14B 120.1 . . ?
H14A C14 H14B 120.0 . . ?
C27 C28 H28A 119.9 . . ?
C27 C28 H28B 120.1 . . ?
H28A C28 H28B 120.0 . . ?
C1 C5 H5A 109.4 . . ?
C1 C5 H5B 109.5 . . ?
H5A C5 H5B 109.5 . . ?
C1 C5 H5C 109.6 . . ?
H5A C5 H5C 109.5 . . ?
H5B C5 H5C 109.5 . . ?
N6 C25 N8 111.5(8) . . ?
N6 C25 C26 113.4(7) . . ?
N8 C25 C26 111.2(10) . . ?
N6 C25 H25 106.7 . . ?
N8 C25 H25 106.7 . . ?
C26 C25 H25 106.8 . . ?
N7 N8 C25 121.5(7) . . ?
N7 N8 C22 107.4(11) . . ?
C25 N8 C22 128.6(8) . . ?
C16 C17 N6 107.0(8) . . ?
C16 C17 C18 132.8(11) . . ?
N6 C17 C18 120.2(13) . . ?
C17 C16 C15 108.4(9) . . ?
C17 C16 H16 125.8 . . ?
C15 C16 H16 125.8 . . ?
C6 C10 H10A 109.4 . . ?
C6 C10 H10B 109.5 . . ?
H10A C10 H10B 109.5 . . ?
C6 C10 H10C 109.5 . . ?
H10A C10 H10C 109.5 . . ?
H10B C10 H10C 109.5 . . ?
F4 B1 F2 117.2(14) . . ?
F4 B1 F3 101.8(13) . . ?
F2 B1 F3 107.1(11) . . ?
F4 B1 F1 104.4(10) . . ?
F2 B1 F1 111.2(8) . . ?
F3 B1 F1 115.0(9) . . ?
C17 C18 H18A 109.3 . . ?
C17 C18 H18B 109.6 . . ?
H18A C18 H18B 109.5 . . ?
C17 C18 H18C 109.5 . . ?
H18A C18 H18C 109.5 . . ?
H18B C18 H18C 109.5 . . ?
C20 C24 H24A 109.7 . . ?
C20 C24 H24B 109.6 . . ?
H24A C24 H24B 109.5 . . ?
C20 C24 H24C 109.1 . . ?
H24A C24 H24C 109.5 . . ?
H24B C24 H24C 109.5 . . ?
N7 C20 C24 123.1(10) . . ?
N7 C20 C21 109.8(8) . . ?
C24 C20 C21 119.2(12) . . ?
C21 C22 C23 119(3) . . ?
C21 C22 N8 106.9(14) . . ?
C23 C22 N8 123.0(13) . . ?
C22 C21 C20 93.7(15) . . ?
C22 C21 H21 133.8 . . ?
C20 C21 H21 132.4 . . ?
C22 C23 H23A 113.5 . . ?
C22 C23 H23B 117.1 . . ?
H23A C23 H23B 105.5 . . ?
C22 C23 H23C 108.8 . . ?
H23A C23 H23C 107.0 . . ?
H23B C23 H23C 104.1 . . ?

_refine_diff_density_max         1.897
_refine_diff_density_min         -0.924
_refine_diff_density_rms         0.139


####################################################################### 
# 
# 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_2a
_database_code_depnum_ccdc_archive 'CCDC 2468990'
loop_
_audit_author_name
_audit_author_address
'Tiago Cruz'
;Centro de Quimica Estrutural, Departamento de Engenharia Quimica, Instituto Superior Tecnico
Portugal
;
_audit_update_record             
;
2025-08-12 deposited with the CCDC.	2025-08-13 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2019/3
_shelx_SHELXL_version_number     2019/3
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_formula_moiety         'C16 H23 B Cu F4 N5'
_chemical_formula_sum            'C16 H23 B Cu F4 N5'
_chemical_melting_point          ?

_exptl_crystal_description       prism
_exptl_crystal_colour            white
_diffrn_ambient_temperature      150
_chemical_formula_weight         435.74

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'
Cu Cu 0.3201 1.2651 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
B B 0.0013 0.0007 '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'

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 21/n'
_space_group_name_Hall           '-P 2yn'
_chemical_absolute_configuration ?

loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -y-1/2, z-1/2'

_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.
;

_cell_length_a                   13.002(4)
_cell_length_b                   8.038(2)
_cell_length_c                   18.973(7)
_cell_angle_alpha                90
_cell_angle_beta                 92.813(10)
_cell_angle_gamma                90
_cell_volume                     1980.4(11)
_cell_formula_units_Z            4
_cell_measurement_temperature    150
_cell_measurement_reflns_used    5403
_cell_measurement_theta_min      2.75
_cell_measurement_theta_max      25.99
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.461
_exptl_crystal_F_000             896
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.300
_exptl_crystal_size_mid          0.150
_exptl_crystal_size_min          0.150
_exptl_absorpt_coefficient_mu    1.149
_shelx_estimated_absorpt_T_min   0.724
_shelx_estimated_absorpt_T_max   0.847
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.724
_exptl_absorpt_correction_T_max  0.847
_exptl_absorpt_process_details   'SADABS (Sheldrick, 1996)'
_exptl_absorpt_special_details   ?
_diffrn_radiation_probe          ?
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_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            48292
_diffrn_reflns_av_unetI/netI     0.0780
_diffrn_reflns_av_R_equivalents  0.2049
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_limit_l_max       24
_diffrn_reflns_theta_min         2.149
_diffrn_reflns_theta_max         27.534
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.940
_diffrn_measured_fraction_theta_full 0.994
_diffrn_reflns_Laue_measured_fraction_max 0.940
_diffrn_reflns_Laue_measured_fraction_full 0.994
_diffrn_reflns_point_group_measured_fraction_max 0.940
_diffrn_reflns_point_group_measured_fraction_full 0.994
_reflns_number_total             4287
_reflns_number_gt                2795
_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'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXL-2019/2 (Sheldrick, 2019)'
_computing_structure_refinement  'SHELXL-2019/2 (Sheldrick, 2019)'
_computing_molecular_graphics    enCIFer
_computing_publication_material  Mercury
_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)+(0.0950P)²+1.5836P] 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         4287
_refine_ls_number_parameters     249
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1007
_refine_ls_R_factor_gt           0.0579
_refine_ls_wR_factor_ref         0.1665
_refine_ls_wR_factor_gt          0.1478
_refine_ls_goodness_of_fit_ref   0.955
_refine_ls_restrained_S_all      0.955
_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
Cu1 Cu 0.51965(4) 0.02687(6) 0.13074(3) 0.03809(19) Uani 1 1 d . . . . .
N1 N 0.6437(2) -0.1195(4) 0.15224(16) 0.0337(7) Uani 1 1 d . . . . .
N4 N 0.6987(2) 0.1492(4) 0.05558(16) 0.0322(7) Uani 1 1 d . . . . .
N2 N 0.7252(2) -0.1154(4) 0.10905(16) 0.0329(7) Uani 1 1 d . . . . .
C13 C 0.3656(3) 0.0244(5) 0.0813(2) 0.0368(9) Uani 1 1 d . . . . .
H13 H 0.312405 0.069376 0.110770 0.044 Uiso 1 1 calc R U . . .
C11 C 0.7170(3) -0.0261(5) 0.04271(19) 0.0307(8) Uani 1 1 d . . . . .
H11 H 0.783129 -0.036021 0.020432 0.037 Uiso 1 1 calc R U . . .
N3 N 0.6077(2) 0.1982(4) 0.08129(17) 0.0366(7) Uani 1 1 d . . . . .
C14 C 0.3952(3) -0.1295(5) 0.0979(2) 0.0417(10) Uani 1 1 d . . . . .
H14A H 0.419152 -0.199598 0.063315 0.050 Uiso 1 1 calc R U . . .
H14B H 0.391916 -0.167157 0.144077 0.050 Uiso 1 1 calc R U . . .
C12 C 0.3672(3) 0.1004(5) 0.00853(18) 0.0304(8) Uani 1 1 d . . . . .
H12A H 0.434164 0.081915 -0.010398 0.037 Uiso 1 1 calc R U . . .
H12B H 0.356805 0.219584 0.012052 0.037 Uiso 1 1 calc R U . . .
C6 C 0.6109(4) 0.3641(5) 0.0816(2) 0.0488(11) Uani 1 1 d . . . . .
N5 N 0.4684(3) 0.1420(6) 0.2230(2) 0.0640(12) Uani 1 1 d . . . . .
C3 C 0.8079(3) -0.1976(6) 0.1385(2) 0.0430(10) Uani 1 1 d . . . . .
F4 F 0.4379(3) 0.9074(5) 0.3841(2) 0.1000(12) Uani 1 1 d . . . . .
C8 C 0.7585(3) 0.2805(5) 0.0385(2) 0.0441(10) Uani 1 1 d . . . . .
C1 C 0.6768(3) -0.2053(5) 0.2089(2) 0.0430(10) Uani 1 1 d . . . . .
C10 C 0.5225(4) 0.4633(6) 0.1104(4) 0.0704(16) Uani 1 1 d . . . . .
H10A H 0.512857 0.564013 0.083734 0.106 Uiso 1 1 calc R U . . .
H10B H 0.538256 0.490139 0.159054 0.106 Uiso 1 1 calc R U . . .
H10C H 0.460543 0.398169 0.106644 0.106 Uiso 1 1 calc R U . . .
C2 C 0.7784(3) -0.2554(6) 0.2020(2) 0.0494(11) Uani 1 1 d . . . . .
H2 H 0.818499 -0.316716 0.234543 0.059 Uiso 1 1 calc R U . . .
C7 C 0.7031(4) 0.4175(6) 0.0554(3) 0.0594(13) Uani 1 1 d . . . . .
H7 H 0.723542 0.527572 0.050361 0.071 Uiso 1 1 calc R U . . .
C5 C 0.6090(4) -0.2357(7) 0.2688(3) 0.0645(14) Uani 1 1 d . . . . .
H5A H 0.619268 -0.149162 0.303337 0.097 Uiso 1 1 calc R U . . .
H5B H 0.625751 -0.341284 0.290038 0.097 Uiso 1 1 calc R U . . .
H5C H 0.538294 -0.236087 0.251633 0.097 Uiso 1 1 calc R U . . .
C15 C 0.4101(4) 0.1957(9) 0.2581(3) 0.0713(17) Uani 1 1 d . . . . .
F1 F 0.3439(6) 0.7413(10) 0.3164(3) 0.191(3) Uani 1 1 d . . . . .
C9 C 0.8613(4) 0.2631(7) 0.0084(3) 0.0627(14) Uani 1 1 d . . . . .
H9A H 0.909455 0.220365 0.043894 0.094 Uiso 1 1 calc R U . . .
H9B H 0.884228 0.369847 -0.007138 0.094 Uiso 1 1 calc R U . . .
H9C H 0.856532 0.187792 -0.030854 0.094 Uiso 1 1 calc R U . . .
C4 C 0.9072(3) -0.2136(8) 0.1020(3) 0.0677(15) Uani 1 1 d . . . . .
H4A H 0.892859 -0.243396 0.053472 0.102 Uiso 1 1 calc R U . . .
H4B H 0.948900 -0.298299 0.124744 0.102 Uiso 1 1 calc R U . . .
H4C H 0.943251 -0.109424 0.104320 0.102 Uiso 1 1 calc R U . . .
B1 B 0.3620(5) 0.7951(10) 0.3811(4) 0.0701(19) Uani 1 1 d . . . . .
C16 C 0.3316(5) 0.2608(13) 0.3029(4) 0.122(4) Uani 1 1 d . . . . .
H16A H 0.265388 0.253497 0.278409 0.183 Uiso 1 1 calc R U . . .
H16B H 0.346563 0.374975 0.314178 0.183 Uiso 1 1 calc R U . . .
H16C H 0.331175 0.196835 0.345608 0.183 Uiso 1 1 calc R U . . .
F2 F 0.3839(5) 0.6558(9) 0.4184(4) 0.198(4) Uani 1 1 d . . . . .
F3 F 0.2790(6) 0.8499(9) 0.4034(6) 0.281(6) 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 N1 2.021(3) . ?
Cu1 N3 2.047(3) . ?
Cu1 N5 2.116(4) . ?
Cu1 C14 2.118(4) . ?
Cu1 C13 2.169(4) . ?
N1 C1 1.331(5) . ?
N1 N2 1.372(4) . ?
N4 C8 1.359(5) . ?
N4 N3 1.360(4) . ?
N4 C11 1.452(5) . ?
N2 C3 1.358(5) . ?
N2 C11 1.448(5) . ?
C13 C14 1.328(6) . ?
C13 C12 1.511(5) . ?
C13 H13 0.9800 . ?
C11 C12 1.547(5) 3_655 ?
C11 H11 0.9800 . ?
N3 C6 1.335(5) . ?
C14 H14A 0.9300 . ?
C14 H14B 0.9300 . ?
C12 H12A 0.9700 . ?
C12 H12B 0.9700 . ?
C6 C7 1.388(7) . ?
C6 C10 1.522(7) . ?
N5 C15 1.120(6) . ?
C3 C2 1.364(6) . ?
C3 C4 1.500(6) . ?
F4 B1 1.336(7) . ?
C8 C7 1.363(7) . ?
C8 C9 1.485(7) . ?
C1 C2 1.393(6) . ?
C1 C5 1.492(7) . ?
C10 H10A 0.9600 . ?
C10 H10B 0.9600 . ?
C10 H10C 0.9600 . ?
C2 H2 0.9300 . ?
C7 H7 0.9300 . ?
C5 H5A 0.9600 . ?
C5 H5B 0.9600 . ?
C5 H5C 0.9600 . ?
C15 C16 1.457(7) . ?
F1 B1 1.312(9) . ?
C9 H9A 0.9600 . ?
C9 H9B 0.9600 . ?
C9 H9C 0.9600 . ?
C4 H4A 0.9600 . ?
C4 H4B 0.9600 . ?
C4 H4C 0.9600 . ?
B1 F2 1.348(9) . ?
B1 F3 1.258(9) . ?
C16 H16A 0.9600 . ?
C16 H16B 0.9600 . ?
C16 H16C 0.9600 . ?

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 Cu1 N3 91.47(13) . . ?
N1 Cu1 N5 111.60(14) . . ?
N3 Cu1 N5 106.90(17) . . ?
N1 Cu1 C14 107.70(15) . . ?
N3 Cu1 C14 134.46(14) . . ?
N5 Cu1 C14 103.65(18) . . ?
N1 Cu1 C13 142.38(14) . . ?
N3 Cu1 C13 109.46(14) . . ?
N5 Cu1 C13 92.31(15) . . ?
C14 Cu1 C13 36.07(16) . . ?
C1 N1 N2 105.5(3) . . ?
C1 N1 Cu1 133.5(3) . . ?
N2 N1 Cu1 119.8(2) . . ?
C8 N4 N3 112.2(3) . . ?
C8 N4 C11 127.8(3) . . ?
N3 N4 C11 119.6(3) . . ?
C3 N2 N1 111.2(3) . . ?
C3 N2 C11 128.4(3) . . ?
N1 N2 C11 120.3(3) . . ?
C14 C13 C12 125.2(4) . . ?
C14 C13 Cu1 69.9(2) . . ?
C12 C13 Cu1 109.8(2) . . ?
C14 C13 H13 114.4 . . ?
C12 C13 H13 114.4 . . ?
Cu1 C13 H13 114.4 . . ?
N4 C11 N2 109.9(3) . . ?
N4 C11 C12 111.3(3) . 3_655 ?
N2 C11 C12 112.0(3) . 3_655 ?
N4 C11 H11 107.8 . . ?
N2 C11 H11 107.8 . . ?
C12 C11 H11 107.8 3_655 . ?
C6 N3 N4 105.3(3) . . ?
C6 N3 Cu1 133.5(3) . . ?
N4 N3 Cu1 119.1(2) . . ?
C13 C14 Cu1 74.0(2) . . ?
C13 C14 H14A 120.0 . . ?
Cu1 C14 H14A 106.8 . . ?
C13 C14 H14B 120.0 . . ?
Cu1 C14 H14B 89.2 . . ?
H14A C14 H14B 120.0 . . ?
C13 C12 C11 112.2(3) . 3_655 ?
C13 C12 H12A 109.2 . . ?
C11 C12 H12A 109.2 3_655 . ?
C13 C12 H12B 109.2 . . ?
C11 C12 H12B 109.2 3_655 . ?
H12A C12 H12B 107.9 . . ?
N3 C6 C7 109.5(4) . . ?
N3 C6 C10 120.1(4) . . ?
C7 C6 C10 130.4(4) . . ?
C15 N5 Cu1 155.6(4) . . ?
N2 C3 C2 106.1(4) . . ?
N2 C3 C4 122.3(4) . . ?
C2 C3 C4 131.6(4) . . ?
N4 C8 C7 104.9(4) . . ?
N4 C8 C9 123.6(4) . . ?
C7 C8 C9 131.5(4) . . ?
N1 C1 C2 110.1(4) . . ?
N1 C1 C5 121.3(4) . . ?
C2 C1 C5 128.5(4) . . ?
C6 C10 H10A 109.5 . . ?
C6 C10 H10B 109.5 . . ?
H10A C10 H10B 109.5 . . ?
C6 C10 H10C 109.5 . . ?
H10A C10 H10C 109.5 . . ?
H10B C10 H10C 109.5 . . ?
C3 C2 C1 107.1(4) . . ?
C3 C2 H2 126.5 . . ?
C1 C2 H2 126.5 . . ?
C8 C7 C6 108.1(4) . . ?
C8 C7 H7 126.0 . . ?
C6 C7 H7 126.0 . . ?
C1 C5 H5A 109.5 . . ?
C1 C5 H5B 109.5 . . ?
H5A C5 H5B 109.5 . . ?
C1 C5 H5C 109.5 . . ?
H5A C5 H5C 109.5 . . ?
H5B C5 H5C 109.5 . . ?
N5 C15 C16 177.9(7) . . ?
C8 C9 H9A 109.5 . . ?
C8 C9 H9B 109.5 . . ?
H9A C9 H9B 109.5 . . ?
C8 C9 H9C 109.5 . . ?
H9A C9 H9C 109.5 . . ?
H9B C9 H9C 109.5 . . ?
C3 C4 H4A 109.5 . . ?
C3 C4 H4B 109.5 . . ?
H4A C4 H4B 109.5 . . ?
C3 C4 H4C 109.5 . . ?
H4A C4 H4C 109.5 . . ?
H4B C4 H4C 109.5 . . ?
F1 B1 F2 104.0(8) . . ?
F1 B1 F3 108.2(8) . . ?
F2 B1 F3 106.1(7) . . ?
F1 B1 F4 111.2(6) . . ?
F2 B1 F4 113.7(6) . . ?
F3 B1 F4 113.2(7) . . ?
C15 C16 H16A 109.5 . . ?
C15 C16 H16B 109.5 . . ?
H16A C16 H16B 109.5 . . ?
C15 C16 H16C 109.5 . . ?
H16A C16 H16C 109.5 . . ?
H16B C16 H16C 109.5 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C1 N1 N2 C3 0.0(4) . . . . ?
Cu1 N1 N2 C3 168.9(3) . . . . ?
C1 N1 N2 C11 -178.0(3) . . . . ?
Cu1 N1 N2 C11 -9.2(4) . . . . ?
C8 N4 C11 N2 119.4(4) . . . . ?
N3 N4 C11 N2 -67.9(4) . . . . ?
C8 N4 C11 C12 -115.9(4) . . . 3_655 ?
N3 N4 C11 C12 56.8(4) . . . 3_655 ?
C3 N2 C11 N4 -116.1(4) . . . . ?
N1 N2 C11 N4 61.6(4) . . . . ?
C3 N2 C11 C12 119.6(4) . . . 3_655 ?
N1 N2 C11 C12 -62.8(4) . . . 3_655 ?
C8 N4 N3 C6 -1.1(4) . . . . ?
C11 N4 N3 C6 -174.9(3) . . . . ?
C8 N4 N3 Cu1 -166.5(3) . . . . ?
C11 N4 N3 Cu1 19.7(4) . . . . ?
C12 C13 C14 Cu1 100.5(4) . . . . ?
C14 C13 C12 C11 71.4(5) . . . 3_655 ?
Cu1 C13 C12 C11 150.3(2) . . . 3_655 ?
N4 N3 C6 C7 0.7(5) . . . . ?
Cu1 N3 C6 C7 163.0(3) . . . . ?
N4 N3 C6 C10 -177.4(4) . . . . ?
Cu1 N3 C6 C10 -15.1(7) . . . . ?
N1 N2 C3 C2 -0.1(5) . . . . ?
C11 N2 C3 C2 177.8(4) . . . . ?
N1 N2 C3 C4 179.4(4) . . . . ?
C11 N2 C3 C4 -2.8(7) . . . . ?
N3 N4 C8 C7 1.1(5) . . . . ?
C11 N4 C8 C7 174.3(4) . . . . ?
N3 N4 C8 C9 -179.2(4) . . . . ?
C11 N4 C8 C9 -6.0(6) . . . . ?
N2 N1 C1 C2 0.0(5) . . . . ?
Cu1 N1 C1 C2 -166.6(3) . . . . ?
N2 N1 C1 C5 179.6(4) . . . . ?
Cu1 N1 C1 C5 13.0(7) . . . . ?
N2 C3 C2 C1 0.1(5) . . . . ?
C4 C3 C2 C1 -179.3(5) . . . . ?
N1 C1 C2 C3 0.0(5) . . . . ?
C5 C1 C2 C3 -179.6(5) . . . . ?
N4 C8 C7 C6 -0.6(5) . . . . ?
C9 C8 C7 C6 179.7(5) . . . . ?
N3 C6 C7 C8 0.0(6) . . . . ?
C10 C6 C7 C8 177.8(5) . . . . ?

_refine_diff_density_max         0.877
_refine_diff_density_min         -0.615
_refine_diff_density_rms         0.083


