Synthesis of unsymmetrical 1,8-naphthyridine-based ligands for the assembly of tri-and tetra-nuclear copper(ii) complexes
Bacher, Felix; Isaac, James A.; Philouze, Christian; Flot, David; Thibon-Pourret, Aurore; Belle, Catherine; New Journal of Chemistry 44 (2020) 16713–16720; doi:10.1039/D0NJ02776F

data_7059825
_publ_section_title
;
 Synthesis of unsymmetrical 1,8-naphthyridine-based ligands for the
 assembly of tri-and tetra-nuclear copper(ii) complexes
;
_journal_issue                   39
_journal_name_full               'New Journal of Chemistry'
_journal_page_first              16713
_journal_page_last               16720
_journal_paper_doi               10.1039/D0NJ02776F
_journal_volume                  44
_journal_year                    2020
_chemical_formula_moiety
'C54 H40 Cu4 N10 O6, 2(C F3 O3 S), 2(C2 H3 N)'
_chemical_formula_sum            'C60 H46 Cu4 F6 N12 O12 S2'
_chemical_formula_weight         1559.37
_space_group_crystal_system      monoclinic
_space_group_IT_number           15
_space_group_name_Hall           '-C 2yc'
_space_group_name_H-M_alt        'C 1 2/c 1'
_atom_sites_solution_hydrogens   mixed
_audit_creation_date             2019-12-10
_audit_creation_method
;
Olex2 1.2
(compiled 2014.07.22 svn.r2960 for OlexSys, GUI svn.r4862)
;
_audit_update_record
;
2019-12-10 deposited with the CCDC.	2020-07-23 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 90.65(3)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   22.949(5)
_cell_length_b                   11.893(2)
_cell_length_c                   22.443(5)
_cell_measurement_reflns_used    54508
_cell_measurement_temperature    200
_cell_measurement_theta_max      27.510
_cell_measurement_theta_min      2.127
_cell_volume                     6125(2)
_computing_cell_refinement       EvalCCD
_computing_data_collection       Collect
_computing_data_reduction        EvalCCD
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_diffrn_ambient_temperature      200
_diffrn_detector                 'CCD area detector'
_diffrn_detector_type            'APEX II'
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device       '\k-geometry 4 circles diffractometer'
_diffrn_measurement_device_type  Incoatec-Bruker-AXS-enraf-noniusKappaAPEXII
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_collimation    'Montel optic'
_diffrn_radiation_detector       CCD
_diffrn_radiation_monochromator  'Multilayer mirrors'
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0614
_diffrn_reflns_av_unetI/netI     0.0309
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       29
_diffrn_reflns_limit_h_min       -29
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       29
_diffrn_reflns_limit_l_min       -29
_diffrn_reflns_number            54508
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.510
_diffrn_reflns_theta_min         2.127
_diffrn_source                   'Incoatec ISG250'
_diffrn_source_target            Mo
_diffrn_source_type              'Microfocus sealed tube'
_exptl_absorpt_coefficient_mu    1.531
_exptl_absorpt_correction_T_max  1
_exptl_absorpt_correction_T_min  0.510312
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2004/1 (Bruker,2004) was used for absorption correction.
R(int) was 0.2327 before and 0.0589 after correction.
The Ratio of minimum to maximum transmission is 0.5103.
The \l/2 correction factor is 0.0015.
;
_exptl_crystal_colour            black
_exptl_crystal_colour_primary    black
_exptl_crystal_density_diffrn    1.691
_exptl_crystal_description       plate
_exptl_crystal_F_000             3152
_exptl_crystal_size_max          0.47
_exptl_crystal_size_mid          0.3
_exptl_crystal_size_min          0.2
_refine_diff_density_max         0.507
_refine_diff_density_min         -0.700
_refine_diff_density_rms         0.083
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.111
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     558
_refine_ls_number_reflns         7031
_refine_ls_number_restraints     503
_refine_ls_restrained_S_all      1.122
_refine_ls_R_factor_all          0.0556
_refine_ls_R_factor_gt           0.0422
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0466P)^2^+22.6631P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1083
_refine_ls_wR_factor_ref         0.1192
_reflns_Friedel_coverage         0.000
_reflns_number_gt                5882
_reflns_number_total             7031
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d0nj02776f2.cif
_cod_data_source_block           sad2
_cod_depositor_comments
'Adding full bibliography for 7059823--7059825.cif.'
_cod_database_code               7059825
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups, All O(H) groups
2. Restrained distances
 S1B-O4B
 1.42 with sigma of 0.02
 O4B-S1B
 1.4 with sigma of 0.02
 S1B-O4B
 1.4 with sigma of 0.002
 S1B-C28
 1.7 with sigma of 0.002
 S1A-C28
 1.7 with sigma of 0.002
 F3A-C28
 1.3 with sigma of 0.002
 F3B-C28
 1.3 with sigma of 0.002
 F1A-C28
 1.3 with sigma of 0.002
 F1B-C28
 1.3 with sigma of 0.002
 C28-F2A
 1.3 with sigma of 0.002
 C28-F2B
 1.3 with sigma of 0.002
 O5B-S1B
 1.4 with sigma of 0.02
 S1B-O6B
 1.4 with sigma of 0.02
 C30C-C29C
 1.5 with sigma of 0.02
 C30C-N6C
 2.6 with sigma of 0.02
 F1B-F3B
 2 with sigma of 0.02
 C29A-C30A
 1.5 with sigma of 0.02
 N6A-C29A
 1.1 with sigma of 0.02
 N6A-C30A
 2.6 with sigma of 0.02
 N6B-C30B
 2.6 with sigma of 0.02
 C29B-C30B
 1.5 with sigma of 0.02
 N6B-C29B
 1.1 with sigma of 0.02
 C28-O6B
 2.54 with sigma of 0.02
 O4B-C28
 2.54 with sigma of 0.02
 O5B-C28
 2.54 with sigma of 0.02
 F2B-S1B
 2.5 with sigma of 0.02
 F1B-S1B
 2.5 with sigma of 0.02
 S1B-F3B
 2.5 with sigma of 0.02
3. Rigid bond restraints
 S1A, O4A, O5A, F1A, O6A, F3A, F2A, C28, S1B, F3B, F2B, F1B, O5B, O6B, O4B
 with sigma for 1-2 distances of 0.01 and sigma for 1-3 distances of 0.01
 C29B, N6A, C30B, H30A, H30B, H30C, C30C, H30G, H30H, H30I, C29C, N6C, C30A,
 H30D, H30E, H30F, C29A, N6B
 with sigma for 1-2 distances of 0.01 and sigma for 1-3 distances of 0.01
4. Uiso/Uaniso restraints and constraints
S1A \\sim O4A \\sim O5A \\sim F1A \\sim O6A \\sim F3A \\sim F2A \\sim C28 \\sim
S1B \\sim F3B \\sim F2B \\sim F1B \\sim O5B \\sim O6B \\sim O4B: within 1.7A
with sigma of 0.04 and sigma for terminal atoms of 0.08
C29B \\sim N6A \\sim C30B \\sim H30A \\sim H30B \\sim H30C \\sim C30C \\sim
H30G \\sim H30H \\sim H30I \\sim C29C \\sim N6C \\sim C30A \\sim H30D \\sim
H30E \\sim H30F \\sim C29A \\sim N6B: within 1.7A with sigma of 0.04 and sigma
for terminal atoms of 0.08
Uanis(F1A) \\sim Ueq, Uanis(F1B) \\sim Ueq, Uanis(O6B) \\sim Ueq: with sigma of
0.01 and sigma for terminal atoms of 0.02
5. Others
 Sof(S1B)=Sof(F3B)=Sof(F2B)=Sof(F1B)=Sof(O5B)=Sof(O6B)=Sof(O4B)=1-FVAR(1)
 Sof(S1A)=Sof(O4A)=Sof(O5A)=Sof(F1A)=Sof(O6A)=Sof(F3A)=Sof(F2A)=FVAR(1)
 Sof(C29B)=Sof(C30B)=Sof(H30A)=Sof(H30B)=Sof(H30C)=Sof(N6B)=0.75*(1-FVAR(3))
 Sof(N6A)=Sof(C30A)=Sof(H30D)=Sof(H30E)=Sof(H30F)=Sof(C29A)=0.75*FVAR(3)
 Fixed Sof: C30C(0.25) H30G(0.25) H30H(0.25) H30I(0.25) C29C(0.25) N6C(0.25)
6.a Free rotating group:
 O3(H3)
6.b Aromatic/amide H refined with riding coordinates:
 C26(H26), C6(H6), C7(H7), C2(H2), C19(H19), C3(H3A), C14(H14), C25(H25),
 C23(H23), C18(H18), C16(H16), C12(H12), C17(H17), C11(H11), C13(H13), C24(H24)
6.c Idealised Me refined with riding coordinates:
 C30C(H30G,H30H,H30I)
6.d Idealised Me refined as rotating group:
 C20(H20A,H20B,H20C), C30B(H30A,H30B,H30C), C30A(H30D,H30E,H30F)
;
_shelx_res_checksum              38951
_shelx_shelxl_version_number     2014/7
_olex2_submission_special_instructions 'No special instructions were received'