Design, synthesis, theoretical study, antioxidant, and anticholinesterase activities of new pyrazolo-fused phenanthrolines
Polo-Cuadrado, Efraín; Rojas-Peña, Cristian; Acosta-Quiroga, Karen; Camargo-Ayala, Lorena; Brito, Iván; Cisterna, Jonathan; Moncada, Félix; Trilleras, Jorge; Rodríguez-Núñez, Yeray A.; Gutierrez, Margarita; RSC Advances 12 (2022) 33032–33048; doi:10.1039/D2RA05532E

data_7245869
_publ_section_title
;
 Design, synthesis, theoretical study, antioxidant, and anticholinesterase
 activities of new pyrazolo-fused phenanthrolines
;
_journal_issue                   51
_journal_name_full               'RSC Advances'
_journal_page_first              33032
_journal_page_last               33048
_journal_paper_doi               10.1039/D2RA05532E
_journal_volume                  12
_journal_year                    2022
_chemical_formula_moiety         'C30 H26 N6 O3'
_chemical_formula_sum            'C30 H26 N6 O3'
_chemical_formula_weight         518.57
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2yn'
_space_group_name_H-M_alt        'P 1 21/n 1'
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     dual
_audit_creation_date             2022-07-18
_audit_creation_method
;
Olex2 1.5
(compiled 2022.04.07 svn.rca3783a0 for OlexSys, GUI svn.r6498)
;
_audit_update_record
;
2022-08-11 deposited with the CCDC.	2022-11-03 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 100.785(2)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   10.0883(8)
_cell_length_b                   12.4670(11)
_cell_length_c                   20.6411(18)
_cell_measurement_reflns_used    6969
_cell_measurement_temperature    295.94
_cell_measurement_theta_max      26.50
_cell_measurement_theta_min      2.95
_cell_volume                     2550.2(4)
_computing_cell_refinement       'SAINT v8.37A (Bruker, 2015)'
_computing_data_reduction        'SAINT v8.37A (Bruker, 2015)'
_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 2018/2 (Sheldrick, 2018)'
_diffrn_ambient_temperature      295.94
_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  0.0427
_diffrn_reflns_av_unetI/netI     0.0318
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.987
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       26
_diffrn_reflns_limit_l_min       -26
_diffrn_reflns_number            25717
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.987
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.008
_diffrn_reflns_theta_min         2.946
_diffrn_source_current           30.0
_diffrn_source_power             1.5
_diffrn_source_voltage           50.0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.090
_exptl_absorpt_correction_T_max  0.7454
_exptl_absorpt_correction_T_min  0.6773
_exptl_absorpt_correction_type   numerical
_exptl_absorpt_process_details
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.0530 before and 0.0479 after correction.
The Ratio of minimum to maximum transmission is 0.9086.
The \l/2 correction factor is Not present.
;
_exptl_crystal_colour            'clear light colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.351
_exptl_crystal_description       block
_exptl_crystal_F_000             1088
_exptl_crystal_size_max          0.18
_exptl_crystal_size_mid          0.16
_exptl_crystal_size_min          0.11
_refine_diff_density_max         0.452
_refine_diff_density_min         -0.296
_refine_diff_density_rms         0.047
_refine_ls_extinction_coef       0.0064(10)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2018/3 (Sheldrick 2018)'
_refine_ls_goodness_of_fit_ref   1.035
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     323
_refine_ls_number_reflns         5498
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.035
_refine_ls_R_factor_all          0.0913
_refine_ls_R_factor_gt           0.0574
_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^)+(0.0590P)^2^+2.0939P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1366
_refine_ls_wR_factor_ref         0.1633
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3791
_reflns_number_total             5498
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d2ra05532e2.cif
_cod_data_source_block           mg_f2_2021
_cod_database_code               7245869
_shelx_shelxl_version_number     2018/3
_shelx_estimated_absorpt_t_max   0.990
_shelx_estimated_absorpt_t_min   0.984
_olex2_refinement_description
;
1. Uiso/Uaniso restraints and constraints
Uanis(C17B) = Uanis(C16B) = Uanis(C7B) = Uanis(C18B) = Uanis(C20B) =
Uanis(C19B) = Uanis(C18A) = Uanis(C17A) = Uanis(C16A) = Uanis(C7A) =
Uanis(C20A) = Uanis(C19A)
2. Others
 Sof(C7A)=Sof(C20A)=Sof(H20A)=Sof(C19A)=Sof(H19A)=Sof(C18A)=Sof(H18A)=
 Sof(C17A)=Sof(H17A)=Sof(C16A)=Sof(H16A)=1-FVAR(1)
 Sof(C7B)=Sof(C20B)=Sof(H20B)=Sof(C19B)=Sof(H19B)=Sof(C18B)=Sof(H18B)=
 Sof(C17B)=Sof(H17B)=Sof(C16B)=Sof(H16B)=FVAR(1)
3.a Rotating group:
 N32(H32A,H32B)
3.b Secondary CH2 refined with riding coordinates:
 C12(H12A,H12B), C13(H13A,H13B)
3.c Aromatic/amide H refined with riding coordinates:
 C26(H26), C30(H30), C11(H11), C20B(H20B), C19B(H19B), C18B(H18B), C17B(H17B),
 C16B(H16B), C20A(H20A), C19A(H19A), C18A(H18A), C17A(H17A), C16A(H16A)
3.d Fitted hexagon refined as free rotating group:
 C7B(C20B,C19B,C18B,C17B,C16B), C7A(C20A,C19A,C18A,C17A,C16A)
3.e Idealised Me refined as rotating group:
 C37(H37A,H37B,H37C), C36(H36A,H36B,H36C), C38(H38A,H38B,H38C), C6(H6A,H6B,H6C)
;
_shelx_res_checksum              98634
_olex2_submission_special_instructions 'No special instructions were received'