A novel quinoline-based NNN-pincer Cu(II) complex as a superior catalyst for oxidative esterification of allylic C(sp<sup>3</sup>)-H bonds.
Das, Krishna Mohan; Pal, Adwitiya; Adarsh, Nayarassery N.; Thakur, Arunabha; Organic & biomolecular chemistry 20 (2022) 3540–3549; doi:10.1039/d2ob00220e

data_7158617
_publ_section_title
;
 A novel quinoline-based NNN-pincer Cu(II) complex as a superior catalyst
 for oxidative esterification of allylic C(sp<sup>3</sup>)-H bonds.
;
_journal_issue                   17
_journal_name_full               'Organic &amp; biomolecular chemistry'
_journal_page_first              3540
_journal_page_last               3549
_journal_paper_doi               10.1039/d2ob00220e
_journal_volume                  20
_journal_year                    2022
_chemical_formula_moiety         'C13 H14 O3'
_chemical_formula_sum            'C13 H14 O3'
_chemical_formula_weight         218.24
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2ybc'
_space_group_name_H-M_alt        'P 1 21/c 1'
_atom_sites_solution_hydrogens   geom
_audit_creation_date             2022-03-15
_audit_creation_method
;
Olex2 1.5
(compiled 2021.12.09 svn.r5202d8cf for OlexSys, GUI svn.r6439)
;
_audit_update_record
;
2022-03-20 deposited with the CCDC.	2022-03-30 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 108.43(3)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   10.881(2)
_cell_length_b                   10.233(2)
_cell_length_c                   11.017(2)
_cell_measurement_reflns_used    9986
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      27.19
_cell_measurement_theta_min      2.79
_cell_volume                     1163.8(4)
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_device_type  'Bruker Apex II'
_diffrn_measurement_method       'phi-omega scan'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0646
_diffrn_reflns_av_unetI/netI     0.0270
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            35191
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.290
_diffrn_reflns_theta_min         1.973
_exptl_absorpt_coefficient_mu    0.088
_exptl_absorpt_correction_T_max  1.0000
_exptl_absorpt_correction_T_min  0.783029
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2004/1 (Bruker,2004) was used for absorption correction.
R(int) was 0.3360 before and 0.0695 after correction.
The Ratio of minimum to maximum transmission is 0.7830.
The \l/2 correction factor is 0.0015.
;
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.246
_exptl_crystal_description       block
_exptl_crystal_F_000             464
_exptl_crystal_size_max          0.32
_exptl_crystal_size_mid          0.22
_exptl_crystal_size_min          0.12
_refine_diff_density_max         0.140
_refine_diff_density_min         -0.174
_refine_diff_density_rms         0.043
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.048
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     209
_refine_ls_number_reflns         2604
_refine_ls_number_restraints     24
_refine_ls_restrained_S_all      1.047
_refine_ls_R_factor_all          0.0776
_refine_ls_R_factor_gt           0.0565
_refine_ls_shift/su_max          0.083
_refine_ls_shift/su_mean         0.010
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0797P)^2^+0.3406P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1555
_refine_ls_wR_factor_ref         0.1735
_reflns_Friedel_coverage         0.000
_reflns_number_gt                1902
_reflns_number_total             2604
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d2ob00220e2.cif
_cod_data_source_block           atoap30_0m_a
_cod_depositor_comments
'Adding full bibliography for 7158616--7158617.cif.'
_cod_original_cell_volume        1163.7(4)
_cod_database_code               7158617
_shelx_shelxl_version_number     2018/3
_shelx_estimated_absorpt_t_max   0.990
_shelx_estimated_absorpt_t_min   0.972
_exptl_absorpt_special_details   multi-scan
_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) groups
2. Restrained distances
 O10-C8 \\sim O10B-C8
 with sigma of 0.01
3. Restrained planarity
 C11, C12, C13, C14
 with sigma of 0.01
 C11B, C12B, C13B, C14B
 with sigma of 0.01
4. Rigid bond restraints
 O10
 with sigma for 1-2 distances of 0.01 and sigma for 1-3 distances of 0.01
5. Uiso/Uaniso restraints and constraints
Uanis(O10) \\sim Ueq: with sigma of 0.01 and sigma for terminal atoms of 0.02
6. Same fragment restrains
{O10, C11, C12, C13, C14, C15, C16} sigma for 1-2: 0.01, 1-3: 0.04
as in
{O10B, C11B, C12B, C13B, C14B, C15B, C16B}
7. Others
 Sof(O10B)=Sof(C11B)=Sof(H11B)=Sof(C12B)=Sof(H12B)=Sof(C13B)=Sof(H13B)=
 Sof(C14B)=Sof(H14C)=Sof(H14D)=Sof(C15B)=Sof(H15C)=Sof(H15D)=Sof(C16B)=
 Sof(H16C)=Sof(H16D)=1-FVAR(1)
 Sof(O10)=Sof(C11)=Sof(H11)=Sof(C12)=Sof(H12)=Sof(C13)=Sof(H13)=Sof(C14)=
 Sof(H14A)=Sof(H14B)=Sof(C15)=Sof(H15A)=Sof(H15B)=Sof(C16)=Sof(H16A)=Sof(H16B)=
 FVAR(1)
8.a Ternary CH refined with riding coordinates:
 C11(H11), C11B(H11B)
8.b Secondary CH2 refined with riding coordinates:
 C14(H14A,H14B), C15(H15A,H15B), C16(H16A,H16B), C14B(H14C,H14D), C15B(H15C,
 H15D), C16B(H16C,H16D)
8.c Aromatic/amide H refined with riding coordinates:
 C3(H3), C4(H4), C6(H6), C7(H7), C12(H12), C13(H13), C12B(H12B), C13B(H13B)
8.d Tetrahedral OH refined with riding coordinates:
 O1(H1)
;
_shelx_res_checksum              47329
_olex2_submission_special_instructions 'No special instructions were received'