# Supplementary Information (SI) for Chemical Science.
# 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. 
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data_0928na
_database_code_depnum_ccdc_archive 'CCDC 2451025'
loop_
_audit_author_name
_audit_author_address
'Tomohiro Higashino'
;Kyoto University
Japan
;
_audit_update_record             
;
2025-05-14 deposited with the CCDC.	2025-07-21 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         '0.25(C28 H32 Cu N4 O4), 0.25(C2 F6 N O4 S2)'
_chemical_formula_sum            'C7.50 H8 Cu0.25 F1.50 N1.25 O2 P0 S0.50'
_chemical_formula_weight         208.07

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'
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'
S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
P P 0.1023 0.0942 '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'

_space_group_crystal_system      orthorhombic
_space_group_IT_number           72
_space_group_name_H-M_alt        'I b a m'
_space_group_name_Hall           '-I 2 2c'

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

_cell_length_a                   8.071(2)
_cell_length_b                   16.120(4)
_cell_length_c                   26.964(8)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     3508.1(16)
_cell_formula_units_Z            16
_cell_measurement_temperature    143(2)
_cell_measurement_reflns_used    4286
_cell_measurement_theta_min      3.7
_cell_measurement_theta_max      27.5

_exptl_crystal_description       prism
_exptl_crystal_colour            orange
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.576
_exptl_crystal_F_000             1704
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.300
_exptl_crystal_size_mid          0.200
_exptl_crystal_size_min          0.100
_exptl_absorpt_coefficient_mu    0.830
_shelx_estimated_absorpt_T_min   0.789
_shelx_estimated_absorpt_T_max   0.922
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.846
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.39.46e (Rigaku Oxford Diffraction, 2018)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      143(2)
_diffrn_radiation_wavelength     0.71075
_diffrn_radiation_type           MoK\a
_diffrn_source                   'Rotating Anode'
_diffrn_measurement_device_type  'Rigaku Saturn724+ (4x4 bin mode)'
_diffrn_measurement_method       'profile data from ω-scans'
_diffrn_detector_area_resol_mean 28.5714
_diffrn_reflns_number            13214
_diffrn_reflns_av_unetI/netI     0.0270
_diffrn_reflns_av_R_equivalents  0.0401
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -20
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_l_min       -34
_diffrn_reflns_limit_l_max       34
_diffrn_reflns_theta_min         3.652
_diffrn_reflns_theta_max         27.473
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measured_fraction_theta_full 0.994
_diffrn_reflns_Laue_measured_fraction_max 0.995
_diffrn_reflns_Laue_measured_fraction_full 0.994
_diffrn_reflns_point_group_measured_fraction_max 0.995
_diffrn_reflns_point_group_measured_fraction_full 0.994
_reflns_number_total             2055
_reflns_number_gt                1835
_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    'SHELXS-2014 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2014 (Sheldrick, 2014)'
_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)+(0.1042P)²+30.6453P] 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         2055
_refine_ls_number_parameters     150
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0597
_refine_ls_R_factor_gt           0.0556
_refine_ls_wR_factor_ref         0.2108
_refine_ls_wR_factor_gt          0.2083
_refine_ls_goodness_of_fit_ref   1.056
_refine_ls_restrained_S_all      1.056
_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 0.0000 0.0000 0.2500 0.0301(3) Uani 1 4 d S T P . .
S1 S 0.43856(18) 0.08069(10) 0.5000 0.0312(4) Uani 1 2 d S T P . .
N1 N 0.1075(4) 0.0958(2) 0.28677(13) 0.0259(7) Uani 1 1 d . . . . .
C2 C 0.0542(5) 0.1711(2) 0.27216(15) 0.0257(8) Uani 1 1 d . . . . .
O1 O 0.2299(5) 0.30971(19) 0.36270(12) 0.0414(8) Uani 1 1 d . . . . .
C3 C 0.0977(5) 0.2434(2) 0.29697(14) 0.0279(8) Uani 1 1 d . . . . .
H7 H 0.0603 0.2958 0.2854 0.034 Uiso 1 1 calc R U . . .
C4 C 0.2069(5) 0.0909(3) 0.32710(16) 0.0303(9) Uani 1 1 d . . . . .
C1 C 0.2142(8) 0.0644(4) 0.5000 0.0362(14) Uani 1 2 d S T P A .
C5 C 0.2545(6) 0.1600(3) 0.35410(15) 0.0306(9) Uani 1 1 d . . . . .
H8 H 0.3247 0.1546 0.3822 0.037 Uiso 1 1 calc R U . . .
C6 C 0.1972(6) 0.2377(2) 0.33909(15) 0.0302(9) Uani 1 1 d . . . . .
C8 C 0.3157(7) 0.3051(3) 0.40929(18) 0.0428(11) Uani 1 1 d . . . . .
H1 H 0.2527 0.2702 0.4323 0.064 Uiso 1 1 calc R U . . .
H2 H 0.3272 0.3609 0.4232 0.064 Uiso 1 1 calc R U . . .
H3 H 0.4259 0.2810 0.4041 0.064 Uiso 1 1 calc R U . . .
C7 C 0.2631(8) 0.0056(3) 0.3414(2) 0.0460(12) Uani 1 1 d . . . . .
H4 H 0.1672 -0.0275 0.3517 0.069 Uiso 1 1 calc R U . . .
H5 H 0.3418 0.0095 0.3690 0.069 Uiso 1 1 calc R U . . .
H6 H 0.3171 -0.0209 0.3130 0.069 Uiso 1 1 calc R U . . .
N3 N 0.5000 0.0000 0.5298(4) 0.033(2) Uani 0.5 2 d S T P B .
F1 F 0.1501(8) 0.0554(5) 0.4559(2) 0.0518(16) Uani 0.5 1 d . . P A 1
F2 F 0.1778(8) -0.0012(5) 0.5262(3) 0.061(2) Uani 0.5 1 d . . P A 1
F3 F 0.1413(8) 0.1285(5) 0.5216(3) 0.072(2) Uani 0.5 1 d . . P A 1
O2 O 0.4876(9) 0.0911(6) 0.4519(3) 0.044(3) Uani 0.517(15) 1 d . . P B 2
O3 O 0.4576(10) 0.1491(6) 0.4650(4) 0.051(3) Uani 0.483(15) 1 d . . P B 3


_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 2.029(3) 3 ?
Cu1 N1 2.029(3) 2 ?
Cu1 N1 2.029(3) 4 ?
Cu1 N1 2.029(3) . ?
S1 O2 1.367(7) 10_556 ?
S1 O2 1.367(7) . ?
S1 O3 1.459(8) . ?
S1 O3 1.459(8) 10_556 ?
S1 N3 1.608(5) 9_656 ?
S1 N3 1.608(5) . ?
S1 C1 1.830(7) . ?
N1 C2 1.347(5) . ?
N1 C4 1.354(5) . ?
C2 C3 1.388(5) . ?
C2 C2 1.481(8) 4 ?
O1 C6 1.350(5) . ?
O1 C8 1.437(6) . ?
C3 C6 1.394(6) . ?
C3 H7 0.9500 . ?
C4 C5 1.386(6) . ?
C4 C7 1.499(6) . ?
C1 F1 1.305(7) . ?
C1 F1 1.305(7) 10_556 ?
C1 F2 1.305(9) . ?
C1 F2 1.305(9) 10_556 ?
C1 F3 1.324(9) 10_556 ?
C1 F3 1.324(9) . ?
C5 C6 1.395(6) . ?
C5 H8 0.9500 . ?
C8 H1 0.9800 . ?
C8 H2 0.9800 . ?
C8 H3 0.9800 . ?
C7 H4 0.9800 . ?
C7 H5 0.9800 . ?
C7 H6 0.9800 . ?
N3 O2 1.552(9) 10_556 ?
N3 O2 1.552(9) 9_656 ?
N3 N3 1.61(2) 9_656 ?
N3 S1 1.607(5) 9_656 ?
F1 F2 1.056(10) 10_556 ?
F1 F3 1.326(11) 10_556 ?
F2 F1 1.056(10) 10_556 ?
F2 F2 1.415(16) 10_556 ?
F3 F3 1.163(16) 10_556 ?
F3 F1 1.326(11) 10_556 ?
O2 N3 1.552(9) 9_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 Cu1 N1 80.96(19) 3 2 ?
N1 Cu1 N1 121.52(19) 3 4 ?
N1 Cu1 N1 129.4(2) 2 4 ?
N1 Cu1 N1 129.4(2) 3 . ?
N1 Cu1 N1 121.52(19) 2 . ?
N1 Cu1 N1 80.96(19) 4 . ?
O2 S1 O2 143.3(7) 10_556 . ?
O3 S1 O3 80.5(9) . 10_556 ?
O2 S1 N3 119.0(5) 10_556 9_656 ?
O2 S1 N3 62.3(5) . 9_656 ?
O3 S1 N3 104.8(5) . 9_656 ?
O3 S1 N3 154.5(4) 10_556 9_656 ?
O2 S1 N3 62.3(5) 10_556 . ?
O2 S1 N3 119.0(5) . . ?
O3 S1 N3 154.5(4) . . ?
O3 S1 N3 104.8(5) 10_556 . ?
N3 S1 N3 60.0(6) 9_656 . ?
O2 S1 C1 107.7(3) 10_556 . ?
O2 S1 C1 107.7(3) . . ?
O3 S1 C1 102.3(4) . . ?
O3 S1 C1 102.3(4) 10_556 . ?
N3 S1 C1 100.9(2) 9_656 . ?
N3 S1 C1 100.9(2) . . ?
C2 N1 C4 118.5(3) . . ?
C2 N1 Cu1 114.0(3) . . ?
C4 N1 Cu1 127.0(3) . . ?
N1 C2 C3 122.3(4) . . ?
N1 C2 C2 115.1(2) . 4 ?
C3 C2 C2 122.6(2) . 4 ?
C6 O1 C8 117.5(4) . . ?
C2 C3 C6 118.9(4) . . ?
C2 C3 H7 120.5 . . ?
C6 C3 H7 120.5 . . ?
N1 C4 C5 122.7(4) . . ?
N1 C4 C7 116.1(4) . . ?
C5 C4 C7 121.2(4) . . ?
F1 C1 F1 131.4(8) . 10_556 ?
F1 C1 F2 108.4(7) . . ?
F1 C1 F2 47.7(5) 10_556 . ?
F1 C1 F2 47.7(5) . 10_556 ?
F1 C1 F2 108.4(7) 10_556 10_556 ?
F2 C1 F2 65.7(9) . 10_556 ?
F1 C1 F3 60.6(5) . 10_556 ?
F1 C1 F3 108.1(7) 10_556 10_556 ?
F2 C1 F3 140.4(7) . 10_556 ?
F2 C1 F3 107.1(6) 10_556 10_556 ?
F1 C1 F3 108.1(7) . . ?
F1 C1 F3 60.6(5) 10_556 . ?
F2 C1 F3 107.1(6) . . ?
F2 C1 F3 140.4(7) 10_556 . ?
F3 C1 F3 52.1(8) 10_556 . ?
F1 C1 S1 114.1(4) . . ?
F1 C1 S1 114.1(4) 10_556 . ?
F2 C1 S1 109.8(5) . . ?
F2 C1 S1 109.8(5) 10_556 . ?
F3 C1 S1 109.1(5) 10_556 . ?
F3 C1 S1 109.1(5) . . ?
C4 C5 C6 118.5(4) . . ?
C4 C5 H8 120.7 . . ?
C6 C5 H8 120.7 . . ?
O1 C6 C3 116.1(4) . . ?
O1 C6 C5 124.8(4) . . ?
C3 C6 C5 119.1(4) . . ?
O1 C8 H1 109.5 . . ?
O1 C8 H2 109.5 . . ?
H1 C8 H2 109.5 . . ?
O1 C8 H3 109.5 . . ?
H1 C8 H3 109.5 . . ?
H2 C8 H3 109.5 . . ?
C4 C7 H4 109.5 . . ?
C4 C7 H5 109.5 . . ?
H4 C7 H5 109.5 . . ?
C4 C7 H6 109.5 . . ?
H4 C7 H6 109.5 . . ?
H5 C7 H6 109.5 . . ?
O2 N3 O2 142.9(9) 10_556 9_656 ?
O2 N3 N3 108.5(5) 10_556 9_656 ?
O2 N3 N3 108.5(5) 9_656 9_656 ?
O2 N3 S1 160.8(5) 10_556 9_656 ?
O2 N3 S1 51.2(3) 9_656 9_656 ?
N3 N3 S1 60.0(3) 9_656 9_656 ?
O2 N3 S1 51.2(3) 10_556 . ?
O2 N3 S1 160.8(5) 9_656 . ?
N3 N3 S1 60.0(3) 9_656 . ?
S1 N3 S1 120.0(6) 9_656 . ?
F2 F1 C1 66.2(6) 10_556 . ?
F2 F1 F3 124.8(8) 10_556 10_556 ?
C1 F1 F3 60.4(5) . 10_556 ?
F1 F2 C1 66.1(6) 10_556 . ?
F1 F2 F2 117.1(6) 10_556 10_556 ?
C1 F2 F2 57.2(5) . 10_556 ?
F3 F3 C1 63.9(4) 10_556 . ?
F3 F3 F1 117.2(4) 10_556 10_556 ?
C1 F3 F1 59.0(5) . 10_556 ?
S1 O2 N3 66.5(5) . 9_656 ?

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
C4 N1 C2 C3 0.0(6) . . . . ?
Cu1 N1 C2 C3 171.9(3) . . . . ?
C4 N1 C2 C2 -179.9(4) . . . 4 ?
Cu1 N1 C2 C2 -8.1(5) . . . 4 ?
N1 C2 C3 C6 -1.4(6) . . . . ?
C2 C2 C3 C6 178.5(5) 4 . . . ?
C2 N1 C4 C5 0.6(6) . . . . ?
Cu1 N1 C4 C5 -170.1(3) . . . . ?
C2 N1 C4 C7 -179.7(4) . . . . ?
Cu1 N1 C4 C7 9.7(6) . . . . ?
O2 S1 C1 F1 178.5(7) 10_556 . . . ?
O2 S1 C1 F1 8.1(8) . . . . ?
O3 S1 C1 F1 51.9(8) . . . . ?
O3 S1 C1 F1 134.7(8) 10_556 . . . ?
N3 S1 C1 F1 -56.1(7) 9_656 . . . ?
N3 S1 C1 F1 -117.3(7) . . . . ?
O2 S1 C1 F1 -8.1(8) 10_556 . . 10_556 ?
O2 S1 C1 F1 -178.5(7) . . . 10_556 ?
O3 S1 C1 F1 -134.7(8) . . . 10_556 ?
O3 S1 C1 F1 -51.9(8) 10_556 . . 10_556 ?
N3 S1 C1 F1 117.3(7) 9_656 . . 10_556 ?
N3 S1 C1 F1 56.1(7) . . . 10_556 ?
O2 S1 C1 F2 -59.6(7) 10_556 . . . ?
O2 S1 C1 F2 130.0(7) . . . . ?
O3 S1 C1 F2 173.8(7) . . . . ?
O3 S1 C1 F2 -103.4(7) 10_556 . . . ?
N3 S1 C1 F2 65.8(6) 9_656 . . . ?
N3 S1 C1 F2 4.6(6) . . . . ?
O2 S1 C1 F2 -130.0(7) 10_556 . . 10_556 ?
O2 S1 C1 F2 59.6(7) . . . 10_556 ?
O3 S1 C1 F2 103.4(7) . . . 10_556 ?
O3 S1 C1 F2 -173.8(7) 10_556 . . 10_556 ?
N3 S1 C1 F2 -4.6(6) 9_656 . . 10_556 ?
N3 S1 C1 F2 -65.8(6) . . . 10_556 ?
O2 S1 C1 F3 112.9(6) 10_556 . . 10_556 ?
O2 S1 C1 F3 -57.5(7) . . . 10_556 ?
O3 S1 C1 F3 -13.7(7) . . . 10_556 ?
O3 S1 C1 F3 69.1(6) 10_556 . . 10_556 ?
N3 S1 C1 F3 -121.7(6) 9_656 . . 10_556 ?
N3 S1 C1 F3 177.1(6) . . . 10_556 ?
O2 S1 C1 F3 57.5(7) 10_556 . . . ?
O2 S1 C1 F3 -112.9(6) . . . . ?
O3 S1 C1 F3 -69.1(6) . . . . ?
O3 S1 C1 F3 13.7(7) 10_556 . . . ?
N3 S1 C1 F3 -177.1(6) 9_656 . . . ?
N3 S1 C1 F3 121.7(6) . . . . ?
N1 C4 C5 C6 0.2(7) . . . . ?
C7 C4 C5 C6 -179.6(4) . . . . ?
C8 O1 C6 C3 173.0(4) . . . . ?
C8 O1 C6 C5 -6.6(7) . . . . ?
C2 C3 C6 O1 -177.5(4) . . . . ?
C2 C3 C6 C5 2.1(6) . . . . ?
C4 C5 C6 O1 178.0(4) . . . . ?
C4 C5 C6 C3 -1.5(6) . . . . ?
O2 S1 N3 O2 138.2(7) . . . 10_556 ?
O3 S1 N3 O2 100.7(12) . . . 10_556 ?
O3 S1 N3 O2 1.6(5) 10_556 . . 10_556 ?
N3 S1 N3 O2 159.2(4) 9_656 . . 10_556 ?
C1 S1 N3 O2 -104.4(4) . . . 10_556 ?
O2 S1 N3 O2 143.6(19) 10_556 . . 9_656 ?
O2 S1 N3 O2 -78.3(18) . . . 9_656 ?
O3 S1 N3 O2 -115.8(16) . . . 9_656 ?
O3 S1 N3 O2 145.2(18) 10_556 . . 9_656 ?
N3 S1 N3 O2 -57.2(18) 9_656 . . 9_656 ?
C1 S1 N3 O2 39.2(19) . . . 9_656 ?
O2 S1 N3 N3 -159.2(4) 10_556 . . 9_656 ?
O2 S1 N3 N3 -21.1(4) . . . 9_656 ?
O3 S1 N3 N3 -58.6(12) . . . 9_656 ?
O3 S1 N3 N3 -157.6(3) 10_556 . . 9_656 ?
C1 S1 N3 N3 96.38(14) . . . 9_656 ?
O2 S1 N3 S1 -159.2(4) 10_556 . . 9_656 ?
O2 S1 N3 S1 -21.1(4) . . . 9_656 ?
O3 S1 N3 S1 -58.6(12) . . . 9_656 ?
O3 S1 N3 S1 -157.6(3) 10_556 . . 9_656 ?
N3 S1 N3 S1 0.002(0) 9_656 . . 9_656 ?
C1 S1 N3 S1 96.38(14) . . . 9_656 ?
F1 C1 F1 F2 -76.6(12) 10_556 . . 10_556 ?
F2 C1 F1 F2 -27.2(7) . . . 10_556 ?
F3 C1 F1 F2 -165.3(7) 10_556 . . 10_556 ?
F3 C1 F1 F2 -143.0(8) . . . 10_556 ?
S1 C1 F1 F2 95.5(7) . . . 10_556 ?
F1 C1 F1 F3 88.8(12) 10_556 . . 10_556 ?
F2 C1 F1 F3 138.1(7) . . . 10_556 ?
F2 C1 F1 F3 165.3(7) 10_556 . . 10_556 ?
F3 C1 F1 F3 22.4(5) . . . 10_556 ?
S1 C1 F1 F3 -99.2(6) . . . 10_556 ?
F1 C1 F2 F1 -129.7(9) . . . 10_556 ?
F2 C1 F2 F1 -151.5(5) 10_556 . . 10_556 ?
F3 C1 F2 F1 -63.9(11) 10_556 . . 10_556 ?
F3 C1 F2 F1 -13.3(7) . . . 10_556 ?
S1 C1 F2 F1 105.0(5) . . . 10_556 ?
F1 C1 F2 F2 21.8(4) . . . 10_556 ?
F1 C1 F2 F2 151.5(5) 10_556 . . 10_556 ?
F3 C1 F2 F2 87.7(9) 10_556 . . 10_556 ?
F3 C1 F2 F2 138.2(6) . . . 10_556 ?
S1 C1 F2 F2 -103.5(4) . . . 10_556 ?
F1 C1 F3 F3 -24.8(4) . . . 10_556 ?
F1 C1 F3 F3 -152.7(5) 10_556 . . 10_556 ?
F2 C1 F3 F3 -141.4(6) . . . 10_556 ?
F2 C1 F3 F3 -69.2(9) 10_556 . . 10_556 ?
S1 C1 F3 F3 99.8(4) . . . 10_556 ?
F1 C1 F3 F1 127.9(9) . . . 10_556 ?
F2 C1 F3 F1 11.3(6) . . . 10_556 ?
F2 C1 F3 F1 83.6(11) 10_556 . . 10_556 ?
F3 C1 F3 F1 152.7(5) 10_556 . . 10_556 ?
S1 C1 F3 F1 -107.5(4) . . . 10_556 ?
O2 S1 O2 N3 102.2(12) 10_556 . . 9_656 ?
O3 S1 O2 N3 177.8(7) . . . 9_656 ?
O3 S1 O2 N3 150.9(5) 10_556 . . 9_656 ?
N3 S1 O2 N3 20.6(4) . . . 9_656 ?
C1 S1 O2 N3 -93.2(3) . . . 9_656 ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
C8 H2 F2 0.98 2.61 3.575(9) 169.1 8
C5 H8 O3 0.95 2.48 3.415(10) 168.5 .
C8 H2 F2 0.98 2.61 3.575(9) 169.1 8

_refine_diff_density_max         0.412
_refine_diff_density_min         -0.445
_refine_diff_density_rms         0.093

_shelxl_version_number           2014-3



####################################################################### 
# 
# 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_0229n2
_database_code_depnum_ccdc_archive 'CCDC 2451026'
loop_
_audit_author_name
_audit_author_address
'Tomohiro Higashino'
;Kyoto University
Japan
;
_audit_update_record             
;
2025-05-14 deposited with the CCDC.	2025-07-21 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C28 H32 Cu N4 O4, F6 P'
_chemical_formula_sum            'C28 H32 Cu F6 N4 O4 P'
_chemical_formula_weight         697.08

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'
P P 0.1023 0.0942 '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      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;

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

_cell_length_a                   9.7349(8)
_cell_length_b                   11.1899(10)
_cell_length_c                   15.3441(12)
_cell_angle_alpha                73.793(8)
_cell_angle_beta                 74.976(7)
_cell_angle_gamma                88.820(7)
_cell_volume                     1547.8(2)
_cell_formula_units_Z            2
_cell_measurement_temperature    143(2)
_cell_measurement_reflns_used    4304
_cell_measurement_theta_min      2.2110
_cell_measurement_theta_max      30.6460

_exptl_crystal_description       prism
_exptl_crystal_colour            orange
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.496
_exptl_crystal_F_000             716
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.280
_exptl_crystal_size_mid          0.030
_exptl_crystal_size_min          0.010
_exptl_absorpt_coefficient_mu    0.833
_shelx_estimated_absorpt_T_min   0.800
_shelx_estimated_absorpt_T_max   0.992
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.89887
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.39.46e (Rigaku Oxford Diffraction, 2018)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      143(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'Rotating Anode'
_diffrn_measurement_device_type  'Rigaku Saturn724+ (4x4 bin mode)'
_diffrn_measurement_method       'profile data from ω-scans'
_diffrn_detector_area_resol_mean 28.5714
_diffrn_reflns_number            11574
_diffrn_reflns_av_unetI/netI     0.1260
_diffrn_reflns_av_R_equivalents  0.0657
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_theta_min         1.898
_diffrn_reflns_theta_max         25.999
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.980
_diffrn_measured_fraction_theta_full 0.985
_diffrn_reflns_Laue_measured_fraction_max 0.980
_diffrn_reflns_Laue_measured_fraction_full 0.985
_diffrn_reflns_point_group_measured_fraction_max 0.980
_diffrn_reflns_point_group_measured_fraction_full 0.985
_reflns_number_total             5949
_reflns_number_gt                3699
_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       'CrysAlisPro 1.171.39.46e (Rigaku OD, 2018)'
_computing_cell_refinement       'CrysAlisPro 1.171.39.46e (Rigaku OD, 2018)'
_computing_data_reduction        'CrysAlisPro 1.171.39.46e (Rigaku OD, 2018)'
_computing_structure_solution    SIR-97
_computing_structure_refinement  'SHELXL-2014 (Sheldrick, 2014)'
_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)+(0.1211P)²+43.5298P] 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         5949
_refine_ls_number_parameters     469
_refine_ls_number_restraints     84
_refine_ls_R_factor_all          0.1736
_refine_ls_R_factor_gt           0.1232
_refine_ls_wR_factor_ref         0.3925
_refine_ls_wR_factor_gt          0.3634
_refine_ls_goodness_of_fit_ref   1.093
_refine_ls_restrained_S_all      1.086
_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
Cu1 Cu 1.05031(17) 0.15569(15) 0.22912(11) 0.0276(5) Uani 1 1 d . . . . .
N1 N 1.1784(10) 0.0723(9) 0.1387(7) 0.023(2) Uani 1 1 d . . . . .
C1 C 1.2700(14) -0.0160(12) 0.1587(9) 0.027(3) Uani 1 1 d . . . . .
C2 C 1.3365(13) -0.0803(12) 0.0955(9) 0.027(3) Uani 1 1 d . . . . .
H1 H 1.4019 -0.1414 0.1115 0.032 Uiso 1 1 calc R U . . .
C3 C 1.3069(13) -0.0549(13) 0.0099(10) 0.032(3) Uani 1 1 d . . . . .
C4 C 1.2148(12) 0.0391(12) -0.0138(8) 0.025(3) Uani 1 1 d . . . . .
H2 H 1.1955 0.0604 -0.0737 0.029 Uiso 1 1 calc R U . . .
C5 C 1.1520(12) 0.1010(11) 0.0531(8) 0.024(3) Uani 1 1 d . . . . .
C6 C 1.0523(12) 0.2016(11) 0.0343(8) 0.023(3) Uani 1 1 d . . . . .
C7 C 1.0200(13) 0.2447(12) -0.0500(9) 0.029(3) Uani 1 1 d . . . . .
H3 H 1.0629 0.2125 -0.1012 0.035 Uiso 1 1 calc R U . . .
C8 C 0.9223(14) 0.3372(13) -0.0590(10) 0.036(3) Uani 1 1 d . . . . .
C9 C 0.8636(14) 0.3852(13) 0.0149(10) 0.036(3) Uani 1 1 d . . . . .
H4 H 0.7989 0.4499 0.0090 0.043 Uiso 1 1 calc R U . . .
C10 C 0.9022(14) 0.3359(12) 0.0989(11) 0.035(3) Uani 1 1 d . . . . .
N2 N 0.9942(11) 0.2454(10) 0.1098(7) 0.025(2) Uani 1 1 d . . . . .
C11 C 1.3008(18) -0.0403(16) 0.2518(10) 0.048(4) Uani 1 1 d . . . . .
H9 H 1.3053 0.0386 0.2672 0.072 Uiso 1 1 calc R U . . .
H10 H 1.3924 -0.0791 0.2495 0.072 Uiso 1 1 calc R U . . .
H11 H 1.2252 -0.0964 0.3000 0.072 Uiso 1 1 calc R U . . .
O1 O 1.3591(10) -0.1164(9) -0.0560(6) 0.037(2) Uani 1 1 d . . . . .
C12 C 1.4484(15) -0.2168(13) -0.0320(10) 0.039(3) Uani 1 1 d . . . . .
H12 H 1.5352 -0.1843 -0.0235 0.058 Uiso 1 1 calc R U . . .
H13 H 1.4738 -0.2571 -0.0827 0.058 Uiso 1 1 calc R U . . .
H14 H 1.3973 -0.2778 0.0266 0.058 Uiso 1 1 calc R U . . .
O2 O 0.8766(10) 0.3869(10) -0.1380(7) 0.040(2) Uani 1 1 d . . . . .
C13 C 0.9324(15) 0.3426(15) -0.2185(11) 0.044(4) Uani 1 1 d . . . . .
H15 H 1.0363 0.3562 -0.2385 0.065 Uiso 1 1 calc R U . . .
H16 H 0.8922 0.3879 -0.2699 0.065 Uiso 1 1 calc R U . . .
H17 H 0.9068 0.2533 -0.2022 0.065 Uiso 1 1 calc R U . . .
C14 C 0.8402(17) 0.3815(14) 0.1835(11) 0.043(4) Uani 1 1 d . . . . .
H18 H 0.7754 0.3161 0.2321 0.065 Uiso 1 1 calc R U . . .
H19 H 0.7875 0.4559 0.1653 0.065 Uiso 1 1 calc R U . . .
H20 H 0.9171 0.4022 0.2081 0.065 Uiso 1 1 calc R U . . .
N3 N 1.0865(10) 0.2312(9) 0.3278(6) 0.020(2) Uani 1 1 d . . . . .
C15 C 1.1867(12) 0.3197(12) 0.3137(9) 0.025(3) Uani 1 1 d . . . . .
C16 C 1.1922(13) 0.3710(11) 0.3854(8) 0.026(3) Uani 1 1 d . . . . .
H5 H 1.2647 0.4331 0.3745 0.031 Uiso 1 1 calc R U . . .
C17 C 1.0946(13) 0.3336(12) 0.4716(9) 0.026(3) Uani 1 1 d . . . . .
C18 C 0.9925(13) 0.2403(12) 0.4850(9) 0.027(3) Uani 1 1 d . . . . .
H6 H 0.9252 0.2108 0.5445 0.033 Uiso 1 1 calc R U . . .
C19 C 0.9877(13) 0.1909(12) 0.4144(8) 0.025(3) Uani 1 1 d . . . . .
C20 C 0.8849(12) 0.0904(11) 0.4229(8) 0.022(3) Uani 1 1 d . . . . .
C21 C 0.7836(12) 0.0347(11) 0.5055(8) 0.024(3) Uani 1 1 d . . . . .
H7 H 0.7797 0.0599 0.5603 0.028 Uiso 1 1 calc R U . . .
C22 C 0.6875(13) -0.0577(11) 0.5094(9) 0.027(3) Uani 1 1 d . . . . .
C23 C 0.6979(15) -0.0919(13) 0.4268(10) 0.036(3) Uani 1 1 d . . . . .
H8 H 0.6359 -0.1560 0.4264 0.044 Uiso 1 1 calc R U . . .
C24 C 0.7994(14) -0.0311(13) 0.3465(9) 0.031(3) Uani 1 1 d . . . . .
N4 N 0.8920(11) 0.0568(10) 0.3443(7) 0.027(2) Uani 1 1 d . . . . .
C25 C 1.2914(15) 0.3572(14) 0.2190(10) 0.040(3) Uani 1 1 d . . . . .
H21 H 1.3256 0.2825 0.2006 0.060 Uiso 1 1 calc R U . . .
H22 H 1.3721 0.4059 0.2215 0.060 Uiso 1 1 calc R U . . .
H23 H 1.2451 0.4080 0.1727 0.060 Uiso 1 1 calc R U . . .
O3 O 1.0898(10) 0.3772(9) 0.5467(6) 0.033(2) Uani 1 1 d . . . . .
C26 C 1.2001(15) 0.4705(13) 0.5340(10) 0.035(3) Uani 1 1 d . . . . .
H24 H 1.2928 0.4331 0.5263 0.052 Uiso 1 1 calc R U . . .
H25 H 1.1804 0.5020 0.5893 0.052 Uiso 1 1 calc R U . . .
H26 H 1.2016 0.5395 0.4779 0.052 Uiso 1 1 calc R U . . .
O4 O 0.5952(10) -0.1079(9) 0.5928(7) 0.039(2) Uani 1 1 d . . . . .
C27 C 0.4948(15) -0.2076(14) 0.6002(12) 0.045(4) Uani 1 1 d . . . . .
H27 H 0.4230 -0.1728 0.5672 0.067 Uiso 1 1 calc R U . . .
H28 H 0.4480 -0.2475 0.6667 0.067 Uiso 1 1 calc R U . . .
H29 H 0.5461 -0.2695 0.5719 0.067 Uiso 1 1 calc R U . . .
C28 C 0.808(2) -0.0621(17) 0.2559(11) 0.061(5) Uani 1 1 d . . . . .
H30 H 0.7539 -0.0038 0.2193 0.091 Uiso 1 1 calc R U . . .
H31 H 0.7692 -0.1474 0.2699 0.091 Uiso 1 1 calc R U . . .
H32 H 0.9083 -0.0555 0.2195 0.091 Uiso 1 1 calc R U . . .
P1A P 0.544(5) 0.647(4) 0.272(4) 0.042(8) Uani 0.43(13) 1 d . U P A 1
F1A F 0.513(8) 0.508(8) 0.355(6) 0.062(16) Uani 0.43(13) 1 d . U P A 1
F2A F 0.711(7) 0.620(7) 0.272(6) 0.055(14) Uani 0.43(13) 1 d . U P A 1
F3A F 0.582(10) 0.784(8) 0.204(7) 0.043(12) Uani 0.43(13) 1 d . U P A 1
F4A F 0.382(8) 0.650(8) 0.292(6) 0.049(13) Uani 0.43(13) 1 d . U P A 1
F5A F 0.543(7) 0.708(7) 0.350(4) 0.046(11) Uani 0.43(13) 1 d . U P A 1
F6A F 0.552(7) 0.569(7) 0.193(5) 0.067(13) Uani 0.43(13) 1 d . U P A 1
P1B P 0.549(3) 0.639(2) 0.263(2) 0.025(5) Uani 0.57(13) 1 d . U P A 2
F1B F 0.526(6) 0.504(6) 0.323(4) 0.057(11) Uani 0.57(13) 1 d . U P A 2
F2B F 0.714(4) 0.645(4) 0.250(3) 0.031(8) Uani 0.57(13) 1 d . U P A 2
F3B F 0.566(8) 0.772(7) 0.192(5) 0.051(12) Uani 0.57(13) 1 d . U P A 2
F4B F 0.377(5) 0.647(6) 0.268(4) 0.041(9) Uani 0.57(13) 1 d . U P A 2
F5B F 0.517(6) 0.687(6) 0.355(4) 0.066(13) Uani 0.57(13) 1 d . U P A 2
F6B F 0.576(6) 0.603(6) 0.171(4) 0.063(10) Uani 0.57(13) 1 d . U P A 2


_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 N2 2.032(10) . ?
Cu1 N1 2.032(9) . ?
Cu1 N3 2.033(9) . ?
Cu1 N4 2.071(10) . ?
N1 C1 1.342(15) . ?
N1 C5 1.352(15) . ?
C1 C2 1.387(16) . ?
C1 C11 1.484(18) . ?
C2 C3 1.369(18) . ?
C3 O1 1.365(15) . ?
C3 C4 1.399(18) . ?
C4 C5 1.401(16) . ?
C5 C6 1.487(17) . ?
C6 C7 1.364(17) . ?
C6 N2 1.366(15) . ?
C7 C8 1.394(18) . ?
C8 O2 1.368(16) . ?
C8 C9 1.38(2) . ?
C9 C10 1.40(2) . ?
C10 N2 1.342(17) . ?
C10 C14 1.50(2) . ?
O1 C12 1.431(16) . ?
O2 C13 1.431(18) . ?
N3 C15 1.337(15) . ?
N3 C19 1.384(15) . ?
C15 C16 1.388(17) . ?
C15 C25 1.496(18) . ?
C16 C17 1.373(17) . ?
C17 O3 1.361(14) . ?
C17 C18 1.391(17) . ?
C18 C19 1.358(17) . ?
C19 C20 1.477(16) . ?
C20 N4 1.345(15) . ?
C20 C21 1.380(16) . ?
C21 C22 1.388(17) . ?
C22 O4 1.335(15) . ?
C22 C23 1.401(19) . ?
C23 C24 1.373(19) . ?
C24 N4 1.336(16) . ?
C24 C28 1.505(18) . ?
O3 C26 1.452(15) . ?
O4 C27 1.459(16) . ?
P1A F4A 1.53(8) . ?
P1A F5A 1.54(7) . ?
P1A F3A 1.59(10) . ?
P1A F2A 1.65(8) . ?
P1A F6A 1.67(9) . ?
P1A F1A 1.68(8) . ?
P1B F1B 1.52(7) . ?
P1B F6B 1.53(6) . ?
P1B F3B 1.56(7) . ?
P1B F2B 1.57(4) . ?
P1B F5B 1.60(6) . ?
P1B F4B 1.66(5) . ?

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
N2 Cu1 N1 80.9(4) . . ?
N2 Cu1 N3 127.4(4) . . ?
N1 Cu1 N3 132.6(4) . . ?
N2 Cu1 N4 118.1(4) . . ?
N1 Cu1 N4 122.2(4) . . ?
N3 Cu1 N4 80.9(4) . . ?
C1 N1 C5 118.8(10) . . ?
C1 N1 Cu1 127.1(8) . . ?
C5 N1 Cu1 113.6(8) . . ?
N1 C1 C2 122.3(11) . . ?
N1 C1 C11 116.9(11) . . ?
C2 C1 C11 120.7(12) . . ?
C3 C2 C1 119.3(12) . . ?
O1 C3 C2 124.9(12) . . ?
O1 C3 C4 115.7(12) . . ?
C2 C3 C4 119.4(11) . . ?
C3 C4 C5 118.3(11) . . ?
N1 C5 C4 121.8(11) . . ?
N1 C5 C6 116.2(10) . . ?
C4 C5 C6 122.0(11) . . ?
C7 C6 N2 123.1(12) . . ?
C7 C6 C5 123.1(11) . . ?
N2 C6 C5 113.8(11) . . ?
C6 C7 C8 118.2(12) . . ?
O2 C8 C9 114.8(12) . . ?
O2 C8 C7 124.8(14) . . ?
C9 C8 C7 120.3(13) . . ?
C8 C9 C10 117.9(13) . . ?
N2 C10 C9 122.9(13) . . ?
N2 C10 C14 116.1(13) . . ?
C9 C10 C14 121.0(13) . . ?
C10 N2 C6 117.6(11) . . ?
C10 N2 Cu1 127.6(9) . . ?
C6 N2 Cu1 114.7(8) . . ?
C3 O1 C12 116.9(11) . . ?
C8 O2 C13 118.7(11) . . ?
C15 N3 C19 119.7(10) . . ?
C15 N3 Cu1 126.2(8) . . ?
C19 N3 Cu1 113.9(8) . . ?
N3 C15 C16 120.5(11) . . ?
N3 C15 C25 116.8(11) . . ?
C16 C15 C25 122.7(12) . . ?
C17 C16 C15 121.0(11) . . ?
O3 C17 C16 126.1(11) . . ?
O3 C17 C18 116.4(11) . . ?
C16 C17 C18 117.5(11) . . ?
C19 C18 C17 121.0(12) . . ?
C18 C19 N3 120.3(11) . . ?
C18 C19 C20 124.7(11) . . ?
N3 C19 C20 115.0(10) . . ?
N4 C20 C21 120.7(11) . . ?
N4 C20 C19 116.4(10) . . ?
C21 C20 C19 122.9(10) . . ?
C20 C21 C22 120.7(11) . . ?
O4 C22 C21 116.4(11) . . ?
O4 C22 C23 126.1(12) . . ?
C21 C22 C23 117.5(11) . . ?
C24 C23 C22 118.9(12) . . ?
N4 C24 C23 122.7(11) . . ?
N4 C24 C28 117.4(12) . . ?
C23 C24 C28 119.9(12) . . ?
C24 N4 C20 119.4(11) . . ?
C24 N4 Cu1 127.1(8) . . ?
C20 N4 Cu1 113.5(8) . . ?
C17 O3 C26 116.3(10) . . ?
C22 O4 C27 118.0(11) . . ?
F4A P1A F5A 91(5) . . ?
F4A P1A F3A 97(5) . . ?
F5A P1A F3A 85(4) . . ?
F4A P1A F2A 168(5) . . ?
F5A P1A F2A 85(4) . . ?
F3A P1A F2A 93(5) . . ?
F4A P1A F6A 92(4) . . ?
F5A P1A F6A 175(5) . . ?
F3A P1A F6A 99(4) . . ?
F2A P1A F6A 91(4) . . ?
F4A P1A F1A 86(4) . . ?
F5A P1A F1A 88(4) . . ?
F3A P1A F1A 172(5) . . ?
F2A P1A F1A 83(4) . . ?
F6A P1A F1A 87(4) . . ?
F1B P1B F6B 93(3) . . ?
F1B P1B F3B 173(5) . . ?
F6B P1B F3B 80(4) . . ?
F1B P1B F2B 95(3) . . ?
F6B P1B F2B 88(3) . . ?
F3B P1B F2B 89(3) . . ?
F1B P1B F5B 91(3) . . ?
F6B P1B F5B 176(3) . . ?
F3B P1B F5B 95(4) . . ?
F2B P1B F5B 93(3) . . ?
F1B P1B F4B 91(3) . . ?
F6B P1B F4B 90(3) . . ?
F3B P1B F4B 85(4) . . ?
F2B P1B F4B 174(3) . . ?
F5B P1B F4B 88(3) . . ?

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
C5 N1 C1 C2 -1.3(19) . . . . ?
Cu1 N1 C1 C2 169.9(10) . . . . ?
C5 N1 C1 C11 177.3(12) . . . . ?
Cu1 N1 C1 C11 -11.6(18) . . . . ?
N1 C1 C2 C3 -1(2) . . . . ?
C11 C1 C2 C3 -179.4(13) . . . . ?
C1 C2 C3 O1 -176.2(12) . . . . ?
C1 C2 C3 C4 2.7(19) . . . . ?
O1 C3 C4 C5 176.7(11) . . . . ?
C2 C3 C4 C5 -2.3(18) . . . . ?
C1 N1 C5 C4 1.6(18) . . . . ?
Cu1 N1 C5 C4 -170.7(9) . . . . ?
C1 N1 C5 C6 -178.5(11) . . . . ?
Cu1 N1 C5 C6 9.1(13) . . . . ?
C3 C4 C5 N1 0.2(18) . . . . ?
C3 C4 C5 C6 -179.7(11) . . . . ?
N1 C5 C6 C7 177.0(11) . . . . ?
C4 C5 C6 C7 -3.1(18) . . . . ?
N1 C5 C6 N2 -4.0(15) . . . . ?
C4 C5 C6 N2 175.9(11) . . . . ?
N2 C6 C7 C8 -0.5(18) . . . . ?
C5 C6 C7 C8 178.4(11) . . . . ?
C6 C7 C8 O2 -178.1(12) . . . . ?
C6 C7 C8 C9 1.6(19) . . . . ?
O2 C8 C9 C10 178.0(11) . . . . ?
C7 C8 C9 C10 -1.7(19) . . . . ?
C8 C9 C10 N2 0.6(19) . . . . ?
C8 C9 C10 C14 -178.7(13) . . . . ?
C9 C10 N2 C6 0.5(18) . . . . ?
C14 C10 N2 C6 179.8(11) . . . . ?
C9 C10 N2 Cu1 -175.3(9) . . . . ?
C14 C10 N2 Cu1 4.0(16) . . . . ?
C7 C6 N2 C10 -0.6(17) . . . . ?
C5 C6 N2 C10 -179.6(10) . . . . ?
C7 C6 N2 Cu1 175.8(9) . . . . ?
C5 C6 N2 Cu1 -3.2(12) . . . . ?
C2 C3 O1 C12 1.7(19) . . . . ?
C4 C3 O1 C12 -177.3(12) . . . . ?
C9 C8 O2 C13 179.9(12) . . . . ?
C7 C8 O2 C13 -0.4(19) . . . . ?
C19 N3 C15 C16 0.2(17) . . . . ?
Cu1 N3 C15 C16 174.3(9) . . . . ?
C19 N3 C15 C25 179.1(11) . . . . ?
Cu1 N3 C15 C25 -6.8(15) . . . . ?
N3 C15 C16 C17 -0.8(19) . . . . ?
C25 C15 C16 C17 -179.6(12) . . . . ?
C15 C16 C17 O3 179.9(12) . . . . ?
C15 C16 C17 C18 1.6(19) . . . . ?
O3 C17 C18 C19 179.7(11) . . . . ?
C16 C17 C18 C19 -1.8(19) . . . . ?
C17 C18 C19 N3 1.2(19) . . . . ?
C17 C18 C19 C20 178.9(12) . . . . ?
C15 N3 C19 C18 -0.4(17) . . . . ?
Cu1 N3 C19 C18 -175.2(10) . . . . ?
C15 N3 C19 C20 -178.3(10) . . . . ?
Cu1 N3 C19 C20 6.9(13) . . . . ?
C18 C19 C20 N4 177.2(12) . . . . ?
N3 C19 C20 N4 -5.0(16) . . . . ?
C18 C19 C20 C21 -1(2) . . . . ?
N3 C19 C20 C21 176.6(11) . . . . ?
N4 C20 C21 C22 0.4(19) . . . . ?
C19 C20 C21 C22 178.7(12) . . . . ?
C20 C21 C22 O4 178.8(11) . . . . ?
C20 C21 C22 C23 0.2(19) . . . . ?
O4 C22 C23 C24 -179.8(13) . . . . ?
C21 C22 C23 C24 -1(2) . . . . ?
C22 C23 C24 N4 2(2) . . . . ?
C22 C23 C24 C28 -177.3(15) . . . . ?
C23 C24 N4 C20 -2(2) . . . . ?
C28 C24 N4 C20 177.9(14) . . . . ?
C23 C24 N4 Cu1 179.9(10) . . . . ?
C28 C24 N4 Cu1 -1(2) . . . . ?
C21 C20 N4 C24 0.4(19) . . . . ?
C19 C20 N4 C24 -178.1(11) . . . . ?
C21 C20 N4 Cu1 179.0(9) . . . . ?
C19 C20 N4 Cu1 0.6(14) . . . . ?
C16 C17 O3 C26 -1.0(18) . . . . ?
C18 C17 O3 C26 177.4(11) . . . . ?
C21 C22 O4 C27 -178.4(12) . . . . ?
C23 C22 O4 C27 0(2) . . . . ?

_refine_diff_density_max         2.139
_refine_diff_density_min         -0.755
_refine_diff_density_rms         0.192

_shelxl_version_number           2014-3



####################################################################### 
# 
# 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_0928na_CCDC1
_database_code_depnum_ccdc_archive 'CCDC 2451027'
loop_
_audit_author_name
_audit_author_address
'Tomohiro Higashino'
;Kyoto University
Japan
;
_audit_update_record             
;
2025-05-14 deposited with the CCDC.	2025-07-21 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C28 H32 Cu N4 O4, B F4'
_chemical_formula_sum            'C28 H32 B Cu F4 N4 O4'
_chemical_formula_weight         638.92

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'
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'
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'
H H 0.0000 0.0000 '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                   14.6532(4)
_cell_length_b                   11.4428(3)
_cell_length_c                   16.8771(5)
_cell_angle_alpha                90
_cell_angle_beta                 95.086(3)
_cell_angle_gamma                90
_cell_volume                     2818.70(14)
_cell_formula_units_Z            4
_cell_measurement_temperature    153(2)
_cell_measurement_reflns_used    14460
_cell_measurement_theta_min      2.4000
_cell_measurement_theta_max      30.9790

_exptl_crystal_description       prism
_exptl_crystal_colour            orange
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.506
_exptl_crystal_F_000             1320
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.300
_exptl_crystal_size_mid          0.200
_exptl_crystal_size_min          0.100
_exptl_absorpt_coefficient_mu    0.843
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.83789
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.39.46e (Rigaku Oxford Diffraction, 2018)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      153(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'Rotating Anode'
_diffrn_measurement_device_type  'Rigaku Saturn724+ (4x4 bin mode)'
_diffrn_measurement_method       'profile data from ω-scans'
_diffrn_detector_area_resol_mean 28.5714
_diffrn_reflns_number            21905
_diffrn_reflns_av_unetI/netI     0.0468
_diffrn_reflns_av_R_equivalents  0.0559
_diffrn_reflns_limit_h_min       -18
_diffrn_reflns_limit_h_max       19
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_theta_min         2.153
_diffrn_reflns_theta_max         27.500
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 1.000
_diffrn_reflns_point_group_measured_fraction_full 1.000
_reflns_number_total             6479
_reflns_number_gt                5471
_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       'CrysAlisPro 1.171.39.46e (Rigaku OD, 2018)'
_computing_cell_refinement       'CrysAlisPro 1.171.39.46e (Rigaku OD, 2018)'
_computing_data_reduction        'CrysAlisPro 1.171.39.46e (Rigaku OD, 2018)'
_computing_structure_solution    'SHELXS-2014 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2014 (Sheldrick, 2014)'
_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)+(0.0316P)²+4.7081P] 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         6479
_refine_ls_number_parameters     387
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0551
_refine_ls_R_factor_gt           0.0453
_refine_ls_wR_factor_ref         0.1104
_refine_ls_wR_factor_gt          0.1053
_refine_ls_goodness_of_fit_ref   1.065
_refine_ls_restrained_S_all      1.065
_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
Cu1 Cu 0.22167(2) 0.76597(3) 0.08414(2) 0.01859(10) Uani 1 1 d . . . . .
N1 N 0.31609(13) 0.88072(18) 0.12897(12) 0.0152(4) Uani 1 1 d . . . . .
O1 O 0.52430(12) 1.11750(16) 0.18706(11) 0.0230(4) Uani 1 1 d . . . . .
O2 O 0.56850(12) 0.64395(17) -0.08048(11) 0.0251(4) Uani 1 1 d . . . . .
N2 N 0.32840(14) 0.71498(18) 0.02147(12) 0.0168(4) Uani 1 1 d . . . . .
F1 F 0.34370(12) 0.17963(15) 0.37435(10) 0.0339(4) Uani 1 1 d . . . . .
N3 N 0.09991(14) 0.79432(18) 0.02021(12) 0.0171(4) Uani 1 1 d . . . . .
O3 O -0.02330(13) 0.37068(17) 0.18701(12) 0.0262(4) Uani 1 1 d . . . . .
C9 C 0.40531(16) 0.7804(2) 0.03687(14) 0.0158(5) Uani 1 1 d . . . . .
F2 F 0.31541(12) 0.36868(16) 0.40510(12) 0.0398(5) Uani 1 1 d . . . . .
C11 C 0.45444(16) 1.0417(2) 0.17116(15) 0.0174(5) Uani 1 1 d . . . . .
C12 C 0.39722(16) 0.8767(2) 0.09526(14) 0.0148(5) Uani 1 1 d . . . . .
O4 O -0.15583(13) 0.82407(18) -0.10146(12) 0.0295(5) Uani 1 1 d . . . . .
N4 N 0.14413(13) 0.64714(18) 0.13769(12) 0.0152(4) Uani 1 1 d . . . . .
C15 C 0.48744(17) 0.6628(2) -0.04966(15) 0.0189(5) Uani 1 1 d . . . . .
C16 C 0.03273(16) 0.7197(2) 0.03610(14) 0.0160(5) Uani 1 1 d . . . . .
F3 F 0.29746(14) 0.30768(18) 0.27646(11) 0.0446(5) Uani 1 1 d . . . . .
C18 C 0.40880(17) 0.5956(2) -0.06629(15) 0.0193(5) Uani 1 1 d . . . . .
H25 H 0.4085 0.5312 -0.1018 0.023 Uiso 1 1 calc R U . . .
C19 C 0.46718(16) 0.9554(2) 0.11482(15) 0.0176(5) Uani 1 1 d . . . . .
H26 H 0.5230 0.9508 0.0903 0.021 Uiso 1 1 calc R U . . .
C20 C 0.08118(17) 0.8773(2) -0.03638(15) 0.0195(5) Uani 1 1 d . . . . .
C21 C 0.11849(17) 0.4783(2) 0.21718(15) 0.0188(5) Uani 1 1 d . . . . .
H27 H 0.1400 0.4268 0.2588 0.023 Uiso 1 1 calc R U . . .
C22 C 0.21638(17) 0.9604(2) 0.22315(17) 0.0234(6) Uani 1 1 d . . . . .
H1 H 0.1654 0.9504 0.1821 0.035 Uiso 1 1 calc R U . . .
H2 H 0.2090 1.0341 0.2513 0.035 Uiso 1 1 calc R U . . .
H3 H 0.2168 0.8953 0.2609 0.035 Uiso 1 1 calc R U . . .
C23 C 0.33070(17) 0.6252(2) -0.02963(15) 0.0188(5) Uani 1 1 d . . . . .
C24 C 0.03390(17) 0.4602(2) 0.17518(16) 0.0195(5) Uani 1 1 d . . . . .
C25 C 0.17137(16) 0.5732(2) 0.19735(15) 0.0164(5) Uani 1 1 d . . . . .
C26 C 0.37279(17) 1.0440(2) 0.20800(15) 0.0179(5) Uani 1 1 d . . . . .
H28 H 0.3635 1.1002 0.2479 0.021 Uiso 1 1 calc R U . . .
C27 C 0.48569(17) 0.7571(2) 0.00261(15) 0.0182(5) Uani 1 1 d . . . . .
H29 H 0.5385 0.8042 0.0144 0.022 Uiso 1 1 calc R U . . .
C28 C 0.26078(17) 0.6007(2) 0.24350(16) 0.0223(5) Uani 1 1 d . . . . .
H4 H 0.3049 0.6273 0.2070 0.033 Uiso 1 1 calc R U . . .
H5 H 0.2844 0.5304 0.2715 0.033 Uiso 1 1 calc R U . . .
H6 H 0.2516 0.6624 0.2823 0.033 Uiso 1 1 calc R U . . .
C29 C 0.51081(18) 1.2104(2) 0.24265(17) 0.0235(6) Uani 1 1 d . . . . .
H7 H 0.4532 1.2510 0.2266 0.035 Uiso 1 1 calc R U . . .
H8 H 0.5619 1.2658 0.2431 0.035 Uiso 1 1 calc R U . . .
H9 H 0.5082 1.1775 0.2960 0.035 Uiso 1 1 calc R U . . .
C30 C 0.00353(17) 0.5390(2) 0.11579(15) 0.0193(5) Uani 1 1 d . . . . .
H30 H -0.0549 0.5297 0.0874 0.023 Uiso 1 1 calc R U . . .
C31 C 0.24337(18) 0.5563(3) -0.04492(18) 0.0280(6) Uani 1 1 d . . . . .
H10 H 0.2222 0.5311 0.0059 0.042 Uiso 1 1 calc R U . . .
H11 H 0.2546 0.4875 -0.0773 0.042 Uiso 1 1 calc R U . . .
H12 H 0.1964 0.6053 -0.0733 0.042 Uiso 1 1 calc R U . . .
C32 C -0.00451(18) 0.8862(2) -0.07699(16) 0.0239(6) Uani 1 1 d . . . . .
H31 H -0.0161 0.9445 -0.1167 0.029 Uiso 1 1 calc R U . . .
C33 C -0.05509(17) 0.7252(2) -0.00122(15) 0.0197(5) Uani 1 1 d . . . . .
H32 H -0.1012 0.6726 0.0127 0.024 Uiso 1 1 calc R U . . .
C34 C 0.05971(16) 0.6313(2) 0.09866(14) 0.0156(5) Uani 1 1 d . . . . .
C35 C -0.07415(17) 0.8094(2) -0.05962(16) 0.0220(5) Uani 1 1 d . . . . .
C36 C 0.15815(19) 0.9580(2) -0.05190(17) 0.0264(6) Uani 1 1 d . . . . .
H13 H 0.1845 0.9913 -0.0015 0.040 Uiso 1 1 calc R U . . .
H14 H 0.1348 1.0210 -0.0874 0.040 Uiso 1 1 calc R U . . .
H15 H 0.2055 0.9143 -0.0769 0.040 Uiso 1 1 calc R U . . .
C37 C 0.30520(17) 0.9622(2) 0.18498(15) 0.0173(5) Uani 1 1 d . . . . .
C38 C 0.57507(19) 0.5441(3) -0.13072(17) 0.0278(6) Uani 1 1 d . . . . .
H16 H 0.5625 0.4732 -0.1011 0.042 Uiso 1 1 calc R U . . .
H17 H 0.6369 0.5398 -0.1484 0.042 Uiso 1 1 calc R U . . .
H18 H 0.5303 0.5511 -0.1772 0.042 Uiso 1 1 calc R U . . .
C39 C 0.0074(2) 0.2865(3) 0.24686(18) 0.0294(6) Uani 1 1 d . . . . .
H19 H 0.0668 0.2547 0.2350 0.044 Uiso 1 1 calc R U . . .
H20 H -0.0374 0.2230 0.2473 0.044 Uiso 1 1 calc R U . . .
H21 H 0.0138 0.3245 0.2991 0.044 Uiso 1 1 calc R U . . .
B1 B 0.2882(2) 0.2767(3) 0.35505(19) 0.0223(6) Uani 1 1 d . . . . .
C41 C -0.23046(18) 0.7490(3) -0.08316(18) 0.0297(7) Uani 1 1 d . . . . .
H22 H -0.2134 0.6672 -0.0908 0.045 Uiso 1 1 calc R U . . .
H23 H -0.2852 0.7677 -0.1185 0.045 Uiso 1 1 calc R U . . .
H24 H -0.2434 0.7611 -0.0278 0.045 Uiso 1 1 calc R U . . .
F4 F 0.19766(13) 0.2492(2) 0.36377(13) 0.0509(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 2.006(2) . ?
Cu1 N3 2.028(2) . ?
Cu1 N4 2.034(2) . ?
Cu1 N2 2.049(2) . ?
N1 C37 1.347(3) . ?
N1 C12 1.363(3) . ?
O1 C11 1.350(3) . ?
O1 C29 1.443(3) . ?
O2 C15 1.356(3) . ?
O2 C38 1.431(3) . ?
N2 C23 1.344(3) . ?
N2 C9 1.359(3) . ?
F1 B1 1.398(3) . ?
N3 C16 1.348(3) . ?
N3 C20 1.357(3) . ?
O3 C24 1.350(3) . ?
O3 C39 1.439(3) . ?
C9 C27 1.383(3) . ?
C9 C12 1.490(3) . ?
F2 B1 1.386(4) . ?
C11 C19 1.395(4) . ?
C11 C26 1.397(3) . ?
C12 C19 1.383(3) . ?
O4 C35 1.345(3) . ?
O4 C41 1.446(3) . ?
N4 C25 1.348(3) . ?
N4 C34 1.361(3) . ?
C15 C18 1.393(3) . ?
C15 C27 1.395(4) . ?
C16 C33 1.383(3) . ?
C16 C34 1.490(3) . ?
F3 B1 1.391(4) . ?
C18 C23 1.390(3) . ?
C18 H25 0.9500 . ?
C19 H26 0.9500 . ?
C20 C32 1.380(4) . ?
C20 C36 1.498(3) . ?
C21 C24 1.388(3) . ?
C21 C25 1.392(3) . ?
C21 H27 0.9500 . ?
C22 C37 1.503(3) . ?
C22 H1 0.9800 . ?
C22 H2 0.9800 . ?
C22 H3 0.9800 . ?
C23 C31 1.506(3) . ?
C24 C30 1.392(4) . ?
C25 C28 1.497(3) . ?
C26 C37 1.393(3) . ?
C26 H28 0.9500 . ?
C27 H29 0.9500 . ?
C28 H4 0.9800 . ?
C28 H5 0.9800 . ?
C28 H6 0.9800 . ?
C29 H7 0.9800 . ?
C29 H8 0.9800 . ?
C29 H9 0.9800 . ?
C30 C34 1.385(3) . ?
C30 H30 0.9500 . ?
C31 H10 0.9800 . ?
C31 H11 0.9800 . ?
C31 H12 0.9800 . ?
C32 C35 1.397(4) . ?
C32 H31 0.9500 . ?
C33 C35 1.389(4) . ?
C33 H32 0.9500 . ?
C36 H13 0.9800 . ?
C36 H14 0.9800 . ?
C36 H15 0.9800 . ?
C38 H16 0.9800 . ?
C38 H17 0.9800 . ?
C38 H18 0.9800 . ?
C39 H19 0.9800 . ?
C39 H20 0.9800 . ?
C39 H21 0.9800 . ?
B1 F4 1.384(3) . ?
C41 H22 0.9800 . ?
C41 H23 0.9800 . ?
C41 H24 0.9800 . ?

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 129.85(8) . . ?
N1 Cu1 N4 131.57(8) . . ?
N3 Cu1 N4 81.00(8) . . ?
N1 Cu1 N2 81.29(8) . . ?
N3 Cu1 N2 116.53(8) . . ?
N4 Cu1 N2 121.39(8) . . ?
C37 N1 C12 118.6(2) . . ?
C37 N1 Cu1 126.65(16) . . ?
C12 N1 Cu1 114.72(16) . . ?
C11 O1 C29 117.2(2) . . ?
C15 O2 C38 117.5(2) . . ?
C23 N2 C9 118.4(2) . . ?
C23 N2 Cu1 127.79(17) . . ?
C9 N2 Cu1 113.75(16) . . ?
C16 N3 C20 118.5(2) . . ?
C16 N3 Cu1 114.61(17) . . ?
C20 N3 Cu1 126.87(17) . . ?
C24 O3 C39 116.9(2) . . ?
N2 C9 C27 122.5(2) . . ?
N2 C9 C12 114.9(2) . . ?
C27 C9 C12 122.6(2) . . ?
O1 C11 C19 116.4(2) . . ?
O1 C11 C26 124.3(2) . . ?
C19 C11 C26 119.2(2) . . ?
N1 C12 C19 122.3(2) . . ?
N1 C12 C9 115.1(2) . . ?
C19 C12 C9 122.6(2) . . ?
C35 O4 C41 117.9(2) . . ?
C25 N4 C34 118.3(2) . . ?
C25 N4 Cu1 127.67(16) . . ?
C34 N4 Cu1 113.18(16) . . ?
O2 C15 C18 124.9(2) . . ?
O2 C15 C27 115.6(2) . . ?
C18 C15 C27 119.5(2) . . ?
N3 C16 C33 123.2(2) . . ?
N3 C16 C34 114.7(2) . . ?
C33 C16 C34 122.1(2) . . ?
C23 C18 C15 118.4(2) . . ?
C23 C18 H25 120.8 . . ?
C15 C18 H25 120.8 . . ?
C12 C19 C11 118.9(2) . . ?
C12 C19 H26 120.6 . . ?
C11 C19 H26 120.6 . . ?
N3 C20 C32 121.3(2) . . ?
N3 C20 C36 116.4(2) . . ?
C32 C20 C36 122.2(2) . . ?
C24 C21 C25 119.0(2) . . ?
C24 C21 H27 120.5 . . ?
C25 C21 H27 120.5 . . ?
C37 C22 H1 109.5 . . ?
C37 C22 H2 109.5 . . ?
H1 C22 H2 109.5 . . ?
C37 C22 H3 109.5 . . ?
H1 C22 H3 109.5 . . ?
H2 C22 H3 109.5 . . ?
N2 C23 C18 122.7(2) . . ?
N2 C23 C31 116.2(2) . . ?
C18 C23 C31 121.1(2) . . ?
O3 C24 C21 125.2(2) . . ?
O3 C24 C30 115.8(2) . . ?
C21 C24 C30 119.0(2) . . ?
N4 C25 C21 122.3(2) . . ?
N4 C25 C28 116.4(2) . . ?
C21 C25 C28 121.3(2) . . ?
C37 C26 C11 118.6(2) . . ?
C37 C26 H28 120.7 . . ?
C11 C26 H28 120.7 . . ?
C9 C27 C15 118.5(2) . . ?
C9 C27 H29 120.7 . . ?
C15 C27 H29 120.7 . . ?
C25 C28 H4 109.5 . . ?
C25 C28 H5 109.5 . . ?
H4 C28 H5 109.5 . . ?
C25 C28 H6 109.5 . . ?
H4 C28 H6 109.5 . . ?
H5 C28 H6 109.5 . . ?
O1 C29 H7 109.5 . . ?
O1 C29 H8 109.5 . . ?
H7 C29 H8 109.5 . . ?
O1 C29 H9 109.5 . . ?
H7 C29 H9 109.5 . . ?
H8 C29 H9 109.5 . . ?
C34 C30 C24 119.1(2) . . ?
C34 C30 H30 120.5 . . ?
C24 C30 H30 120.5 . . ?
C23 C31 H10 109.5 . . ?
C23 C31 H11 109.5 . . ?
H10 C31 H11 109.5 . . ?
C23 C31 H12 109.5 . . ?
H10 C31 H12 109.5 . . ?
H11 C31 H12 109.5 . . ?
C20 C32 C35 119.9(2) . . ?
C20 C32 H31 120.1 . . ?
C35 C32 H31 120.1 . . ?
C16 C33 C35 118.4(2) . . ?
C16 C33 H32 120.8 . . ?
C35 C33 H32 120.8 . . ?
N4 C34 C30 122.2(2) . . ?
N4 C34 C16 115.1(2) . . ?
C30 C34 C16 122.7(2) . . ?
O4 C35 C33 124.9(2) . . ?
O4 C35 C32 116.4(2) . . ?
C33 C35 C32 118.7(2) . . ?
C20 C36 H13 109.5 . . ?
C20 C36 H14 109.5 . . ?
H13 C36 H14 109.5 . . ?
C20 C36 H15 109.5 . . ?
H13 C36 H15 109.5 . . ?
H14 C36 H15 109.5 . . ?
N1 C37 C26 122.4(2) . . ?
N1 C37 C22 116.9(2) . . ?
C26 C37 C22 120.7(2) . . ?
O2 C38 H16 109.5 . . ?
O2 C38 H17 109.5 . . ?
H16 C38 H17 109.5 . . ?
O2 C38 H18 109.5 . . ?
H16 C38 H18 109.5 . . ?
H17 C38 H18 109.5 . . ?
O3 C39 H19 109.5 . . ?
O3 C39 H20 109.5 . . ?
H19 C39 H20 109.5 . . ?
O3 C39 H21 109.5 . . ?
H19 C39 H21 109.5 . . ?
H20 C39 H21 109.5 . . ?
F4 B1 F2 109.6(2) . . ?
F4 B1 F3 109.6(2) . . ?
F2 B1 F3 109.9(2) . . ?
F4 B1 F1 109.7(2) . . ?
F2 B1 F1 109.3(2) . . ?
F3 B1 F1 108.7(2) . . ?
O4 C41 H22 109.5 . . ?
O4 C41 H23 109.5 . . ?
H22 C41 H23 109.5 . . ?
O4 C41 H24 109.5 . . ?
H22 C41 H24 109.5 . . ?
H23 C41 H24 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
C23 N2 C9 C27 -0.7(4) . . . . ?
Cu1 N2 C9 C27 177.6(2) . . . . ?
C23 N2 C9 C12 -178.9(2) . . . . ?
Cu1 N2 C9 C12 -0.6(3) . . . . ?
C29 O1 C11 C19 177.4(2) . . . . ?
C29 O1 C11 C26 -3.6(4) . . . . ?
C37 N1 C12 C19 -2.1(3) . . . . ?
Cu1 N1 C12 C19 175.01(19) . . . . ?
C37 N1 C12 C9 177.1(2) . . . . ?
Cu1 N1 C12 C9 -5.8(3) . . . . ?
N2 C9 C12 N1 4.2(3) . . . . ?
C27 C9 C12 N1 -174.0(2) . . . . ?
N2 C9 C12 C19 -176.6(2) . . . . ?
C27 C9 C12 C19 5.1(4) . . . . ?
C38 O2 C15 C18 -3.3(4) . . . . ?
C38 O2 C15 C27 176.4(2) . . . . ?
C20 N3 C16 C33 -1.5(4) . . . . ?
Cu1 N3 C16 C33 179.8(2) . . . . ?
C20 N3 C16 C34 179.6(2) . . . . ?
Cu1 N3 C16 C34 1.0(3) . . . . ?
O2 C15 C18 C23 179.6(2) . . . . ?
C27 C15 C18 C23 -0.1(4) . . . . ?
N1 C12 C19 C11 0.2(4) . . . . ?
C9 C12 C19 C11 -178.9(2) . . . . ?
O1 C11 C19 C12 -178.9(2) . . . . ?
C26 C11 C19 C12 2.0(4) . . . . ?
C16 N3 C20 C32 0.2(4) . . . . ?
Cu1 N3 C20 C32 178.7(2) . . . . ?
C16 N3 C20 C36 -179.9(2) . . . . ?
Cu1 N3 C20 C36 -1.4(3) . . . . ?
C9 N2 C23 C18 1.0(4) . . . . ?
Cu1 N2 C23 C18 -177.08(19) . . . . ?
C9 N2 C23 C31 -179.6(2) . . . . ?
Cu1 N2 C23 C31 2.3(3) . . . . ?
C15 C18 C23 N2 -0.6(4) . . . . ?
C15 C18 C23 C31 -180.0(3) . . . . ?
C39 O3 C24 C21 -1.4(4) . . . . ?
C39 O3 C24 C30 178.6(2) . . . . ?
C25 C21 C24 O3 178.5(2) . . . . ?
C25 C21 C24 C30 -1.5(4) . . . . ?
C34 N4 C25 C21 3.6(3) . . . . ?
Cu1 N4 C25 C21 -165.04(18) . . . . ?
C34 N4 C25 C28 -174.4(2) . . . . ?
Cu1 N4 C25 C28 17.0(3) . . . . ?
C24 C21 C25 N4 -1.3(4) . . . . ?
C24 C21 C25 C28 176.6(2) . . . . ?
O1 C11 C26 C37 178.7(2) . . . . ?
C19 C11 C26 C37 -2.3(4) . . . . ?
N2 C9 C27 C15 0.0(4) . . . . ?
C12 C9 C27 C15 178.1(2) . . . . ?
O2 C15 C27 C9 -179.3(2) . . . . ?
C18 C15 C27 C9 0.4(4) . . . . ?
O3 C24 C30 C34 -178.1(2) . . . . ?
C21 C24 C30 C34 1.9(4) . . . . ?
N3 C20 C32 C35 0.5(4) . . . . ?
C36 C20 C32 C35 -179.3(3) . . . . ?
N3 C16 C33 C35 2.0(4) . . . . ?
C34 C16 C33 C35 -179.2(2) . . . . ?
C25 N4 C34 C30 -3.1(3) . . . . ?
Cu1 N4 C34 C30 167.07(19) . . . . ?
C25 N4 C34 C16 177.2(2) . . . . ?
Cu1 N4 C34 C16 -12.6(3) . . . . ?
C24 C30 C34 N4 0.4(4) . . . . ?
C24 C30 C34 C16 -180.0(2) . . . . ?
N3 C16 C34 N4 7.8(3) . . . . ?
C33 C16 C34 N4 -171.0(2) . . . . ?
N3 C16 C34 C30 -171.8(2) . . . . ?
C33 C16 C34 C30 9.3(4) . . . . ?
C41 O4 C35 C33 1.8(4) . . . . ?
C41 O4 C35 C32 -177.8(2) . . . . ?
C16 C33 C35 O4 179.1(3) . . . . ?
C16 C33 C35 C32 -1.2(4) . . . . ?
C20 C32 C35 O4 179.7(3) . . . . ?
C20 C32 C35 C33 0.0(4) . . . . ?
C12 N1 C37 C26 1.7(4) . . . . ?
Cu1 N1 C37 C26 -174.97(18) . . . . ?
C12 N1 C37 C22 -177.4(2) . . . . ?
Cu1 N1 C37 C22 5.9(3) . . . . ?
C11 C26 C37 N1 0.4(4) . . . . ?
C11 C26 C37 C22 179.6(2) . . . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
C28 H5 F3 0.98 2.56 3.433(3) 148.9 .
C29 H7 F3 0.98 2.58 3.414(3) 142.4 1_565
C31 H11 F1 0.98 2.49 3.415(3) 156.5 4_565
C18 H25 F1 0.95 2.61 3.415(3) 142.7 4_565
C19 H26 F2 0.95 2.54 3.382(3) 147.4 2_655
C26 H28 F1 0.95 2.36 3.269(3) 159.8 1_565
C26 H28 F3 0.95 2.62 3.447(3) 145.2 1_565
C27 H29 F2 0.95 2.54 3.427(3) 155.4 2_655
C28 H5 F3 0.98 2.56 3.433(3) 148.9 .
C29 H7 F3 0.98 2.58 3.414(3) 142.4 1_565
C31 H11 F1 0.98 2.49 3.415(3) 156.5 4_565
C18 H25 F1 0.95 2.61 3.415(3) 142.7 4_565
C19 H26 F2 0.95 2.54 3.382(3) 147.4 2_655
C26 H28 F1 0.95 2.36 3.269(3) 159.8 1_565
C26 H28 F3 0.95 2.62 3.447(3) 145.2 1_565
C27 H29 F2 0.95 2.54 3.427(3) 155.4 2_655
C28 H5 F3 0.98 2.56 3.433(3) 148.9 .
C29 H7 F3 0.98 2.58 3.414(3) 142.4 1_565
C31 H11 F1 0.98 2.49 3.415(3) 156.5 4_565
C18 H25 F1 0.95 2.61 3.415(3) 142.7 4_565
C19 H26 F2 0.95 2.54 3.382(3) 147.4 2_655
C26 H28 F1 0.95 2.36 3.269(3) 159.8 1_565
C26 H28 F3 0.95 2.62 3.447(3) 145.2 1_565
C27 H29 F2 0.95 2.54 3.427(3) 155.4 2_655
C28 H5 F3 0.98 2.56 3.433(3) 148.9 .
C29 H7 F3 0.98 2.58 3.414(3) 142.4 1_565
C31 H11 F1 0.98 2.49 3.415(3) 156.5 4_565
C18 H25 F1 0.95 2.61 3.415(3) 142.7 4_565
C19 H26 F2 0.95 2.54 3.382(3) 147.4 2_655
C26 H28 F1 0.95 2.36 3.269(3) 159.8 1_565
C26 H28 F3 0.95 2.62 3.447(3) 145.2 1_565
C27 H29 F2 0.95 2.54 3.427(3) 155.4 2_655
C28 H5 F3 0.98 2.56 3.433(3) 148.9 .
C29 H7 F3 0.98 2.58 3.414(3) 142.4 1_565
C31 H11 F1 0.98 2.49 3.415(3) 156.5 4_565

_refine_diff_density_max         0.526
_refine_diff_density_min         -0.427
_refine_diff_density_rms         0.078

_shelxl_version_number           2014-3



