Ln(iii) complexes with a chiral 1H-pyrazolo[3,4-b]pyridine derivative fused with a (−)-α-pinene moiety: synthesis, crystal structure, and photophysical studies in solution and in the solid state
Bryleva, Yuliya A.; Ustimenko, Yuliya P.; Plyusnin, Victor F.; Mikheilis, Alexsandr V.; Shubin, Aleksandr A.; Glinskaya, Ludmila A.; Komarov, Vladislav Yu.; Agafontsev, Alexander M.; Tkachev, Alexey V.; New Journal of Chemistry 45 (2021) 2276–2284; doi:10.1039/D0NJ05277A

data_7060299
_publ_section_title
;
 Ln(iii) complexes with a chiral 1H-pyrazolo[3,4-b]pyridine derivative
 fused with a (&#x2212;)-\a-pinene moiety: synthesis, crystal structure,
 and photophysical studies in solution and in the solid state
;
_journal_issue                   4
_journal_name_full               'New Journal of Chemistry'
_journal_page_first              2276
_journal_page_last               2284
_journal_paper_doi               10.1039/D0NJ05277A
_journal_volume                  45
_journal_year                    2021
_chemical_absolute_configuration ad
_chemical_formula_moiety         'C38 H40 Eu N11 O9, C2 H3 N'
_chemical_formula_sum            'C40 H43 Eu N12 O9'
_chemical_formula_weight         987.82
_space_group_crystal_system      orthorhombic
_space_group_IT_number           18
_space_group_name_Hall           'P 2 2ab'
_space_group_name_H-M_alt        'P 21 21 2'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2018-11-15
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_audit_update_record
;
2020-08-05 deposited with the CCDC.	2020-12-30 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   11.3607(7)
_cell_length_b                   17.4615(11)
_cell_length_c                   10.4929(7)
_cell_measurement_reflns_used    4581
_cell_measurement_temperature    150
_cell_measurement_theta_max      26.49
_cell_measurement_theta_min      2.26
_cell_volume                     2081.5(2)
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_diffrn_ambient_temperature      150
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.987
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0714
_diffrn_reflns_av_unetI/netI     0.0724
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.987
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_k_max       20
_diffrn_reflns_limit_k_min       -23
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            13495
_diffrn_reflns_point_group_measured_fraction_full 0.987
_diffrn_reflns_point_group_measured_fraction_max 0.966
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         28.699
_diffrn_reflns_theta_min         1.941
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    1.577
_exptl_absorpt_correction_T_max  0.7459
_exptl_absorpt_correction_T_min  0.6425
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
'SADABS-2012/1 (Bruker,2012) was used for absorption correction. wR2(int) was 0.0464 before and 0.0259 after correction. The Ratio of minimum to maximum transmission is 0.8614. The \l/2 correction factor is 0.0015.'
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.576
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plank
_exptl_crystal_F_000             1004
_exptl_crystal_preparation       Luminescent
_exptl_crystal_recrystallization_method
'Re-crystallisation from solvent: CH3CN'
_exptl_crystal_size_max          0.3
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.1
_refine_diff_density_max         0.756
_refine_diff_density_min         -1.412
_refine_diff_density_rms         0.119
_refine_ls_abs_structure_details
;
 Flack x determined using 1697 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.012(9)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.060
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     284
_refine_ls_number_reflns         5200
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.060
_refine_ls_R_factor_all          0.0496
_refine_ls_R_factor_gt           0.0425
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0198P)^2^+2.7969P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0793
_refine_ls_wR_factor_ref         0.0821
_reflns_Friedel_coverage         0.732
_reflns_Friedel_fraction_full    0.973
_reflns_Friedel_fraction_max     0.939
_reflns_number_gt                4685
_reflns_number_total             5200
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d0nj05277a2.cif
_cod_data_source_block           a504
_cod_depositor_comments          'Adding full bibliography for 7060299.cif.'
_cod_database_code               7060299
_shelx_shelxl_version_number     2014/7
_shelx_estimated_absorpt_t_max   0.858
_shelx_estimated_absorpt_t_min   0.649
_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 C(H,H,H) groups
2. Others
 Fixed Sof: C20(0.5) C21(0.5) H21A(0.5) H21B(0.5) H21C(0.5) N7(0.5)
3.a Ternary CH refined with riding coordinates:
 C1(H1), C5(H5)
3.b Secondary CH2 refined with riding coordinates:
 C4(H4A,H4B), C7(H7A,H7B)
3.c Aromatic/amide H refined with riding coordinates:
 C10(H10), C16(H16), C17(H17), C18(H18), C19(H19)
3.d Idealised Me refined as rotating group:
 C8(H8A,H8B,H8C), C9(H9A,H9B,H9C), C14(H14A,H14B,H14C), C21(H21A,H21B,H21C)
;
_shelx_res_checksum              37155
_olex2_submission_special_instructions 'No special instructions were received'