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_7059823
_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         'C70 H72 Cu3 N10 O6, H2 O'
_chemical_formula_sum            'C70 H74 Cu3 N10 O7'
_chemical_formula_weight         1358.01
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_atom_sites_solution_hydrogens   mixed
_audit_creation_date             2020-03-30
_audit_creation_method
;
Olex2 1.2
(compiled 2014.07.22 svn.r2960 for OlexSys, GUI svn.r4862)
;
_audit_update_record
;
2020-03-30 deposited with the CCDC.	2020-07-23 downloaded from the CCDC.
;
_cell_angle_alpha                107.44(3)
_cell_angle_beta                 116.00(3)
_cell_angle_gamma                91.19(3)
_cell_formula_units_Z            2
_cell_length_a                   14.798(3)
_cell_length_b                   15.401(3)
_cell_length_c                   16.328(3)
_cell_measurement_reflns_used    35660
_cell_measurement_temperature    100
_cell_measurement_theta_max      31.420
_cell_measurement_theta_min      1.444
_cell_volume                     3140.2(16)
_computing_cell_refinement       'XDS (Kabsch, 2010)'
_computing_data_collection       'mxCuBE (Gabadinho et al., 2010)'
_computing_data_reduction        'XDS (Kabsch, 2010)'
_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      100.0
_diffrn_detector                 'CCD PIXEL area detector'
_diffrn_detector_type            'DECTRIS Pilatus_6M_F'
_diffrn_measured_fraction_theta_full 0.920
_diffrn_measured_fraction_theta_max 0.843
_diffrn_measurement_device       '2 circles diffractometer'
_diffrn_measurement_device_type
'Maatel Mini-diffractometer (ESRF-EMBL, MD2M)'
_diffrn_measurement_method       oscillation
_diffrn_radiation_collimation    'Toroidal mirror'
_diffrn_radiation_monochromator  'Silicon 111'
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           synchrotron
_diffrn_radiation_wavelength     0.729
_diffrn_reflns_av_R_equivalents  0.0000
_diffrn_reflns_av_unetI/netI     0.0892
_diffrn_reflns_Laue_measured_fraction_full 0.920
_diffrn_reflns_Laue_measured_fraction_max 0.843
_diffrn_reflns_limit_h_max       18
_diffrn_reflns_limit_h_min       -20
_diffrn_reflns_limit_k_max       20
_diffrn_reflns_limit_k_min       -21
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_limit_l_min       0
_diffrn_reflns_number            16002
_diffrn_reflns_point_group_measured_fraction_full 0.920
_diffrn_reflns_point_group_measured_fraction_max 0.843
_diffrn_reflns_theta_full        26.000
_diffrn_reflns_theta_max         31.420
_diffrn_reflns_theta_min         1.444
_diffrn_source                   synchrotron
_diffrn_source_type              'Undulator u35 u20, ID23-1, ESRF'
_exptl_absorpt_coefficient_mu    1.138
_exptl_absorpt_correction_T_max  1
_exptl_absorpt_correction_T_min  0.485541
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2004/1 (Bruker,2004) was used for absorption correction.
R(int) was 0.0625 before and 0.0435 after correction.
The Ratio of minimum to maximum transmission is 0.4855.
The \l/2 correction factor is 0.0015.
;
_exptl_crystal_colour            black
_exptl_crystal_colour_primary    black
_exptl_crystal_density_diffrn    1.436
_exptl_crystal_description       needle
_exptl_crystal_F_000             1414
_exptl_crystal_size_max          0.168
_exptl_crystal_size_mid          0.014
_exptl_crystal_size_min          0.014
_refine_diff_density_max         1.806
_refine_diff_density_min         -1.181
_refine_diff_density_rms         0.158
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.375
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     1068
_refine_ls_number_reflns         16002
_refine_ls_number_restraints     818
_refine_ls_restrained_S_all      1.346
_refine_ls_R_factor_all          0.1766
_refine_ls_R_factor_gt           0.1296
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.2000P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.3859
_refine_ls_wR_factor_ref         0.4096
_reflns_Friedel_coverage         0.000
_reflns_number_gt                8807
_reflns_number_total             16002
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d0nj02776f2.cif
_cod_data_source_block           test2
_cod_depositor_comments
'Adding full bibliography for 7059823--7059825.cif.'
_cod_original_cell_volume        3140.0(14)
_cod_database_code               7059823
_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,H) groups
2. Restrained distances
 C67A-C66
 1.5 with sigma of 0.02
 C68A-C66
 1.5 with sigma of 0.02
 C66-C69A
 1.5 with sigma of 0.02
 C67B-C66
 1.5 with sigma of 0.02
 C68B-C66
 1.5 with sigma of 0.02
 C66-C69B
 1.5 with sigma of 0.02
 C50B-C51B
 1.4 with sigma of 0.02
 C51B-C52B
 1.4 with sigma of 0.02
 C52B-C53B
 1.4 with sigma of 0.02
 C53B-C54B
 1.4 with sigma of 0.02
 N9B-C54B
 1.4 with sigma of 0.02
 C50B-N9B
 1.4 with sigma of 0.02
 C50B-C52B
 2.4 with sigma of 0.02
 C51B-C53B
 2.4 with sigma of 0.02
 C52B-C54B
 2.4 with sigma of 0.02
 C53B-N9B
 2.4 with sigma of 0.02
 C54B-C50B
 2.4 with sigma of 0.02
 N9B-C51B
 2.4 with sigma of 0.02
 C18B-C17B
 1.4 with sigma of 0.02
 C17B-C16B
 1.4 with sigma of 0.02
 N5B-C18B
 2.4 with sigma of 0.02
 C18B-C16B
 2.4 with sigma of 0.02
 N5B-C16B
 2.4 with sigma of 0.02
 C15-C17B
 2.4 with sigma of 0.02
 N5B-C15
 1.4 with sigma of 0.02
 C16B-C15
 1.4 with sigma of 0.02
 C19B-C18B
 1.4 with sigma of 0.02
 C19B-N5B
 1.4 with sigma of 0.02
 C19B-C15
 2.4 with sigma of 0.02
 C19B-C17B
 2.4 with sigma of 0.02
 C45A-C47A
 2.4 with sigma of 0.02
 C46A-C48A
 2.4 with sigma of 0.02
 C47A-C49A
 2.4 with sigma of 0.02
 C48A-N8A
 2.4 with sigma of 0.02
 C49A-C45A
 2.4 with sigma of 0.02
 N8A-C46A
 2.4 with sigma of 0.02
 C45A-C46A
 1.4 with sigma of 0.02
 C46A-C47A
 1.4 with sigma of 0.02
 C47A-C48A
 1.4 with sigma of 0.02
 C48A-C49A
 1.4 with sigma of 0.02
 C49A-N8A
 1.4 with sigma of 0.02
 N8A-C45A
 1.4 with sigma of 0.02
3. Rigid bond restraints
 C66, C69A, C67A, C68A, C68B, C67B, C69B
 with sigma for 1-2 distances of 0.01 and sigma for 1-3 distances of 0.01
 N9A, C54A, C51A, C50A, C52A, C53A, C54B, C51B, N9B, C53B, C50B, C52B
 with sigma for 1-2 distances of 0.01 and sigma for 1-3 distances of 0.01
 C10B, C11B, N4B, C14B, C13B, C12B, C14A, C13A, C12A, C11A, C10A, N4A
 with sigma for 1-2 distances of 0.01 and sigma for 1-3 distances of 0.01
 C15, N5A, N5B, C19B, C19A, C18A, C18B, C17A, C17B, C16A, C16B
 with sigma for 1-2 distances of 0.01 and sigma for 1-3 distances of 0.01
 N8B, C45B, C45A, C46A, C46B, C47A, C47B, N8A, C49B, C49A, C48B, C48A
 with sigma for 1-2 distances of 0.01 and sigma for 1-3 distances of 0.01
4. Uiso/Uaniso restraints and constraints
C66 \\sim C69A \\sim C67A \\sim C68A \\sim C68B \\sim C67B \\sim C69B: within
1.7A with sigma of 0.04 and sigma for terminal atoms of 0.08
C50A \\sim C51A \\sim C52A \\sim C53A \\sim C54A \\sim N9A \\sim C50B \\sim
C51B \\sim C52B \\sim C53B \\sim C54B \\sim N9B: within 1.7A with sigma of 0.04
and sigma for terminal atoms of 0.08
C10A \\sim C10B \\sim C11B \\sim C11A \\sim C12A \\sim C13A \\sim C14A \\sim
N4A \\sim N4B \\sim C14B \\sim C12B \\sim C13B: within 1.7A with sigma of 0.04
and sigma for terminal atoms of 0.08
N5B \\sim C19B \\sim C19A \\sim N5A \\sim C15 \\sim C16A \\sim C16B \\sim C17B
\\sim C17A \\sim C18B \\sim C18A: within 1.7A with sigma of 0.04 and sigma for
terminal atoms of 0.08
N8B \\sim N8A \\sim C45B \\sim C45A \\sim C46A \\sim C46B \\sim C47A \\sim C47B
\\sim C48A \\sim C48B \\sim C49A \\sim C49B: within 1.7A with sigma of 0.04 and
sigma for terminal atoms of 0.08
Uanis(C15) = Uanis(C19B)
5. Others
 Sof(H6B)=Sof(H5B)=Sof(N8B)=Sof(C49B)=Sof(H49B)=Sof(C48B)=Sof(H48B)=Sof(Cu3B)=
 Sof(C54B)=Sof(H54E)=Sof(C51B)=Sof(H51B)=Sof(N9B)=Sof(C53B)=Sof(H53B)=Sof(C50B)=
 Sof(C52B)=Sof(H52B)=Sof(N4B)=Sof(C13B)=Sof(H13B)=Sof(C11B)=Sof(H11B)=Sof(C14B)=
 Sof(H14B)=Sof(C10B)=Sof(C12B)=Sof(H12B)=Sof(N5B)=Sof(C18B)=Sof(H18B)=Sof(C17B)=
 Sof(H17B)=Sof(C16B)=Sof(H16B)=Sof(C19B)=Sof(H19B)=Sof(C47B)=Sof(H47B)=
 Sof(C46B)=Sof(H46B)=Sof(C45B)=1-FVAR(1)
 Sof(H6A)=Sof(H5A)=Sof(C10A)=Sof(N4A)=Sof(N9A)=Sof(C45A)=Sof(N5A)=Sof(C13A)=
 Sof(H13A)=Sof(C46A)=Sof(H46A)=Sof(C54A)=Sof(H54D)=Sof(C14A)=Sof(H14A)=
 Sof(C51A)=Sof(H51A)=Sof(C18A)=Sof(H18A)=Sof(C12A)=Sof(H12A)=Sof(C50A)=
 Sof(C47A)=Sof(H47A)=Sof(C16A)=Sof(H16A)=Sof(C11A)=Sof(H11A)=Sof(C52A)=
 Sof(H52A)=Sof(C19A)=Sof(H19A)=Sof(C17A)=Sof(H17A)=Sof(C53A)=Sof(H53A)=
 Sof(Cu3A)=Sof(C49A)=Sof(H49A)=Sof(C48A)=Sof(H48A)=Sof(N8A)=FVAR(1)
 Sof(C68B)=Sof(H68D)=Sof(H68E)=Sof(H68F)=Sof(C67B)=Sof(H67D)=Sof(H67E)=
 Sof(H67F)=Sof(C69B)=Sof(H69D)=Sof(H69E)=Sof(H69F)=1-FVAR(2)
 Sof(C69A)=Sof(H69A)=Sof(H69B)=Sof(H69C)=Sof(C67A)=Sof(H67A)=Sof(H67B)=
 Sof(H67C)=Sof(C68A)=Sof(H68A)=Sof(H68B)=Sof(H68C)=FVAR(2)
6.a Riding coordinates:
 O6(H6A), O6(H6B), O5(H5A), O5(H5B), O7(H7A,H7B)
6.b Aromatic/amide H refined with riding coordinates:
 C6(H6), C38(H38), C23(H23), C42(H42), C41(H41), C3(H3), C2(H2), C7(H7),
 C57(H57), C59(H59), C37(H37), C25(H25), C13A(H13A), C46A(H46A), C54A(H54D),
 C49B(H49B), C14A(H14A), C51A(H51A), C18A(H18A), C12A(H12A), C47A(H47A),
 C16A(H16A), C48B(H48B), C11A(H11A), C52A(H52A), C19A(H19A), C17A(H17A),
 C53A(H53A), C54B(H54E), C51B(H51B), C53B(H53B), C52B(H52B), C13B(H13B),
 C11B(H11B), C14B(H14B), C12B(H12B), C18B(H18B), C17B(H17B), C16B(H16B),
 C19B(H19B), C49A(H49A), C48A(H48A), C47B(H47B), C46B(H46B)
6.c Idealised Me refined as rotating group:
 C64(H64A,H64B,H64C), C65(H65A,H65B,H65C), C20(H20A,H20B,H20C), C30(H30A,H30B,
 H30C), C31(H31A,H31B,H31C), C29(H29A,H29B,H29C), C54(H54A,H54B,H54C), C63(H63A,
 H63B,H63C), C35(H35A,H35B,H35C), C34(H34A,H34B,H34C), C33(H33A,H33B,H33C),
 C69A(H69A,H69B,H69C), C67A(H67A,H67B,H67C), C68A(H68A,H68B,H68C), C68B(H68D,
 H68E,H68F), C67B(H67D,H67E,H67F), C69B(H69D,H69E,H69F)
;
_shelx_res_checksum              33862
_shelx_shelxl_version_number     2014/7
_olex2_submission_special_instructions 'No special instructions were received'