(S)-BINOL-derived chiral picolinate ligand as a platform for new polymer frameworks: a pilot study on the effect of the binaphthyl scaffold vs. picolinate
Rodríguez, Humberto A.; Cruz, Daniel A.; Padrón, Juan I.; Lorenzo-Luis, Pablo; New Journal of Chemistry 49 (2025) 12940–12947; doi:10.1039/D5NJ01654A

data_7063863
_publ_section_title
;
 (S)-BINOL-derived chiral picolinate ligand as a platform for new polymer
 frameworks: a pilot study on the effect of the binaphthyl scaffold vs.
 picolinate
;
_journal_issue                   30
_journal_name_full               'New Journal of Chemistry'
_journal_page_first              12940
_journal_page_last               12947
_journal_paper_doi               10.1039/D5NJ01654A
_journal_volume                  49
_journal_year                    2025
_chemical_formula_moiety         'C17 H17 Cu2 N3 O6, 2(C F3 O3 S), 2(C5 H5 N)'
_chemical_formula_sum            'C29 H27 Cu2 F6 N5 O12 S2'
_chemical_formula_weight         942.778
_space_group_crystal_system      tetragonal
_space_group_IT_number           88
_space_group_name_Hall           '-I 4ad'
_space_group_name_H-M_alt        'I 41/a :2'
_symmetry_Int_Tables_number      88
_atom_sites_solution_primary     dual
_audit_creation_date             2024-12-12
_audit_creation_method
;
Olex2 1.5
(compiled 2024.02.16 svn.r378c4104 for OlexSys, GUI svn.r6928)
;
_audit_update_record
;
2024-12-12 deposited with the CCDC.	2025-06-26 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   14.5386(4)
_cell_length_b                   14.5386(4)
_cell_length_c                   38.0549(9)
_cell_measurement_reflns_used    4426
_cell_measurement_temperature    298(2)
_cell_measurement_theta_max      24.6600
_cell_measurement_theta_min      2.8970
_cell_volume                     8043.7(4)
_computing_cell_refinement       'CrysAlisPro 1.171.42.94a (Rigaku OD, 2023)'
_computing_data_collection       'CrysAlisPro 1.171.42.94a (Rigaku OD, 2023)'
_computing_data_reduction        'CrysAlisPro 1.171.42.94a (Rigaku OD, 2023)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'olex2.refine 1.5 (Bourhis et al., 2015)'
_computing_structure_solution    'SHELXT  (Sheldrick, 2015)'
_diffrn_ambient_temperature      298(2)
_diffrn_detector_area_resol_mean 8.1268
_diffrn_detector_type            EosS2
_diffrn_measured_fraction_theta_full 0.9956
_diffrn_measured_fraction_theta_max 0.9957
_diffrn_measurement_details
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  t~exp~   \w     \q     \k     \f   Frames
  1  \w     29.00  92.00   1.00   30.00    --   26.01  57.00 120.00   63
  2  \w     61.00  86.00   1.00   30.00    --   26.01 178.00 -60.00   25
  3  \w     63.00 117.00   1.00   30.00    --   26.01 178.00  30.00   54
  4  \w     63.00 117.00   1.00   30.00    --   26.01 178.00 -90.00   54
  5  \w   -118.00 -44.00   1.00   30.00    --  -27.26-178.00 -60.00   74
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dualflex, EosS2'
_diffrn_measurement_method       '\w scans'
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0326
_diffrn_reflns_av_unetI/netI     0.0357
_diffrn_reflns_Laue_measured_fraction_full 0.9956
_diffrn_reflns_Laue_measured_fraction_max 0.9957
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -18
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_l_max       48
_diffrn_reflns_limit_l_min       -42
_diffrn_reflns_number            16298
_diffrn_reflns_point_group_measured_fraction_full 0.9956
_diffrn_reflns_point_group_measured_fraction_max 0.9957
_diffrn_reflns_theta_full        25.2417
_diffrn_reflns_theta_max         25.50
_diffrn_reflns_theta_min         2.13
_exptl_absorpt_coefficient_mu    1.250
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.439
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.42.94a (Rigaku Oxford Diffraction, 2023)
Numerical absorption correction based on gaussian integration over
a multifaceted crystal model
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            blue
_exptl_crystal_colour_primary    blue
_exptl_crystal_density_diffrn    1.557
_exptl_crystal_description       block
_exptl_crystal_F_000             3818.942
_exptl_crystal_size_max          0.27
_exptl_crystal_size_mid          0.21
_exptl_crystal_size_min          0.12
_refine_diff_density_max         1.4432
_refine_diff_density_min         -0.6357
_refine_diff_density_rms         0.1502
_refine_ls_d_res_high            0.8255
_refine_ls_d_res_low             9.5582
_refine_ls_goodness_of_fit_ref   1.0827
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_constraints    52
_refine_ls_number_parameters     375
_refine_ls_number_reflns         3731
_refine_ls_number_restraints     450
_refine_ls_restrained_S_all      1.0167
_refine_ls_R_factor_all          0.1061
_refine_ls_R_factor_gt           0.0887
_refine_ls_shift/su_max          0.0009
_refine_ls_shift/su_mean         0.0001
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.1425P)^2^+70.9507P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2628
_refine_ls_wR_factor_ref         0.2800
_reflns_Friedel_coverage         0.0
_reflns_limit_h_max              17
_reflns_limit_h_min              0
_reflns_limit_k_max              17
_reflns_limit_k_min              0
_reflns_limit_l_max              45
_reflns_limit_l_min              0
_reflns_number_gt                2893
_reflns_number_total             3731
_reflns_threshold_expression     I>=2u(I)
_cod_data_source_file            d5nj01654a2.cif
_cod_data_source_block           H8b
_cod_depositor_comments
'Adding full bibliography for 7063861--7063863.cif.'
_cod_original_sg_symbol_H-M      'I 41/a'
_cod_database_code               7063863
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All O(H,H) groups
2. Restrained distances
 N3A-C12A = C12A-C13A = C13A-C14 = C14-C15A = C15A-C16A = C16A-N3A
 1.39 with sigma of 0.01
 N2A-C7A = C7A-C8A = C8A-C9A = C9A-C10A = C10A-C11A = C11A-N2A
 1.39 with sigma of 0.01
 N2B-C7B = C7B-C8B = C8B-C9B = C9B-C10B = C10B-C11B = C11B-N2B
 1.39 with sigma of 0.01
 N3A-C16A = C16A-C15A = C15A-C14 = C14-C13A = C13A-C12A = C12A-N3A
 1.39 with sigma of 0.01
 N1-C6 = C6-C5 = C5-C4 = C4-C3 = C3-C2 = C2-N1
 1.39 with sigma of 0.01
 N3B-C12B = C12B-C13B = C13B-C14 = C14-C15B = C15B-C16B = C16B-N3B
 1.39 with sigma of 0.01
 N3A-C13A \\sim C12A-C14 \\sim C13A-C15A \\sim C14-C16A \\sim C15A-N3A \\sim
C16A-C12A
 with sigma of 0.02
 Cu2-N2A \\sim Cu2-N2B
 with sigma of 0.02
 N2A-C11A \\sim N2B-C11B
 with sigma of 0.02
 C9A-C10A \\sim C9B-C10B
 with sigma of 0.02
 C11A-C10A \\sim C11B-C10B
 with sigma of 0.02
 Cu2-C11A \\sim Cu2-C11B
 with sigma of 0.04
 N2A-C10A \\sim N2B-C10B
 with sigma of 0.04
 C9A-C11A \\sim C9B-C11B
 with sigma of 0.04
 N2A-C8A \\sim C7A-C9A \\sim C8A-C10A \\sim C9A-C11A \\sim C10A-N2A \\sim
C11A-C7A
 with sigma of 0.02
 N2B-C8B \\sim C7B-C9B \\sim C8B-C10B \\sim C9B-C11B \\sim C10B-N2B \\sim
C11B-C7B
 with sigma of 0.02
 N3A-C15A \\sim C16A-C14 \\sim C15A-C13A \\sim C14-C12A \\sim C13A-N3A \\sim
C12A-C16A
 with sigma of 0.02
 N3A-C12A \\sim N3B-C16B
 with sigma of 0.02
 N3A-C16A \\sim N3B-C12B
 with sigma of 0.02
 C14-C15A \\sim C14-C13B
 with sigma of 0.02
 C14-C13A \\sim C14-C15B
 with sigma of 0.02
 C12A-C13A \\sim C16B-C15B
 with sigma of 0.02
 C15A-C16A \\sim C13B-C12B
 with sigma of 0.02
 N3A-C15A \\sim N3B-C13B
 with sigma of 0.04
 N3A-C13A \\sim N3B-C15B
 with sigma of 0.04
 C14-C12A \\sim C14-C16B
 with sigma of 0.04
 C14-C16A \\sim C14-C12B
 with sigma of 0.04
 C12A-C16A \\sim C16B-C12B
 with sigma of 0.04
 N1-C5 \\sim C6-C4 \\sim C5-C3 \\sim C4-C2 \\sim C3-N1 \\sim C2-C6
 with sigma of 0.02
 N3B-C13B \\sim C12B-C14 \\sim C13B-C15B \\sim C14-C16B \\sim C15B-N3B \\sim
C16B-C12B
 with sigma of 0.02
3. Restrained planarity
 N3A, C12A, C13A, C14, C15A, C16A
 with sigma of 0.1
 N2A, C7A, C8A, C9A, C10A, C11A
 with sigma of 0.1
 N2B, C7B, C8B, C9B, C10B, C11B
 with sigma of 0.1
 N3A, C16A, C15A, C14, C13A, C12A
 with sigma of 0.1
 N1, C6, C5, C4, C3, C2
 with sigma of 0.1
 N3B, C12B, C13B, C14, C15B, C16B
 with sigma of 0.1
4. Uiso/Uaniso restraints and constraints
C9A \\sim C11A \\sim C10A \\sim C11B \\sim C10B \\sim N2B \\sim C9B \\sim C7B
\\sim C8B \\sim C7A \\sim C8A \\sim N2A \\sim C9A \\sim C11A \\sim C10A \\sim
C11B \\sim C10B \\sim N2B \\sim C9B \\sim C7B \\sim C8B \\sim C7A \\sim C8A:
within 2A with sigma of 0.005 and sigma for terminal atoms of 0.01 within 2A
C12B \\sim N3A \\sim C12A \\sim C16A \\sim C13A \\sim C15A \\sim C14 \\sim C15B
\\sim C13B \\sim C16B \\sim N3B: within 2A with sigma of 0.005 and sigma for
terminal atoms of 0.01 within 2A
5. Others
 Sof(H14a)=Sof(C15B)=Sof(H15B)=Sof(N3B)=Sof(C16B)=Sof(H16B)=Sof(C12B)=
 Sof(H12B)=Sof(C13B)=Sof(H13B)=1-FVAR(1)
 Sof(N3A)=Sof(H14)=Sof(C12A)=Sof(H12A)=Sof(C15A)=Sof(H15A)=Sof(C16A)=Sof(H16A)=
 Sof(C13A)=Sof(H13A)=FVAR(1)
 Fixed Sof: N2A(0.25) C9A(0.25) H9A(0.25) C11A(0.25) H11A(0.25) C10A(0.25)
 H10A(0.25) C11B(0.25) H11B(0.25) C10B(0.25) H10B(0.25) N2B(0.25) C9B(0.25)
 H9B(0.25) C7B(0.25) H7B(0.25) C8B(0.25) H8B(0.25) C7A(0.25) H7A(0.25)
 C8A(0.25) H8A(0.25)
6.a Rotating group:
 O1W(H1Wa,H1Wb)
6.b Aromatic/amide H refined with riding coordinates:
 C6(H6), C3(H3), C4(H4), C5(H5), C14(H14), C14(H14a), C12A(H12A), C15A(H15A),
 C16A(H16A), C13A(H13A), C9A(H9A), C11A(H11A), C10A(H10A), C11B(H11B),
 C10B(H10B), C9B(H9B), C7B(H7B), C8B(H8B), C7A(H7A), C8A(H8A), C15B(H15B),
 C16B(H16B), C12B(H12B), C13B(H13B)
;
_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;