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_7245868
_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         'C28 H22 N6'
_chemical_formula_sum            'C28 H22 N6'
_chemical_formula_weight         442.51
_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   mixed
_atom_sites_solution_primary     direct
_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                 101.663(3)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   10.4257(14)
_cell_length_b                   13.8104(17)
_cell_length_c                   16.570(2)
_cell_measurement_reflns_used    5925
_cell_measurement_temperature    296.86
_cell_measurement_theta_max      25.94
_cell_measurement_theta_min      2.91
_cell_volume                     2336.5(5)
_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    'SHELXS  (Sheldrick, 2008)'
_diffrn_ambient_temperature      296.86
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.997
_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  0.0433
_diffrn_reflns_av_unetI/netI     0.0357
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            18109
_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         26.045
_diffrn_reflns_theta_min         2.873
_diffrn_source_current           30.0
_diffrn_source_power             1.5
_diffrn_source_voltage           50.0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.078
_exptl_absorpt_correction_T_max  0.7453
_exptl_absorpt_correction_T_min  0.6121
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.0682 before and 0.0522 after correction.
The Ratio of minimum to maximum transmission is 0.8213.
The \l/2 correction factor is Not present.
;
_exptl_crystal_colour            'clear light yellow'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.258
_exptl_crystal_description       block
_exptl_crystal_F_000             928
_exptl_crystal_size_max          0.21
_exptl_crystal_size_mid          0.18
_exptl_crystal_size_min          0.15
_refine_diff_density_max         0.401
_refine_diff_density_min         -0.262
_refine_diff_density_rms         0.052
_refine_ls_extinction_coef       0.0076(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   1.053
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     336
_refine_ls_number_reflns         4602
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.053
_refine_ls_R_factor_all          0.0963
_refine_ls_R_factor_gt           0.0604
_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^)+(0.0461P)^2^+2.6132P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1327
_refine_ls_wR_factor_ref         0.1641
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3161
_reflns_number_total             4602
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d2ra05532e2.cif
_cod_data_source_block           mg_k4me2021
_cod_original_cell_volume        2336.6(5)
_cod_database_code               7245868
_shelx_shelxl_version_number     2018/3
_shelx_estimated_absorpt_t_max   0.988
_shelx_estimated_absorpt_t_min   0.984
_olex2_refinement_description
;
1. Uiso/Uaniso restraints and constraints
Uanis(C13A) = Uanis(C13B) = Uanis(C13C)
Uanis(C12C) = Uanis(C12B) = Uanis(C12A)
Uanis(C29A) = Uanis(C29B)
Uanis(N33A) = Uanis(N33B)
2. Others
 Fixed Sof: C29A(0.5) C12B(0.3333) H12A(0.3333) H12B(0.3333) C13B(0.3333)
 H13A(0.3333) H13B(0.3333) C12A(0.3333) H12C(0.3333) H12D(0.3333) C13C(0.3333)
 H13C(0.3333) H13D(0.3333) C13A(0.3333) H13E(0.3333) H13F(0.3333) C12C(0.3333)
 H12E(0.3333) H12F(0.3333) N33B(0.5) N33A(0.5) C29B(0.5)
3.a Secondary CH2 refined with riding coordinates:
 C12B(H12A,H12B), C13B(H13A,H13B), C12A(H12C,H12D), C13C(H13C,H13D), C13A(H13E,
 H13F), C12C(H12E,H12F)
3.b Aromatic/amide H refined with riding coordinates:
 C11(H11), C30(H30), C34(H34), C16(H16), C20(H20), C26(H26), C27(H27),
 C17(H17), C18(H18), C19(H19)
3.c Idealised Me refined as rotating group:
 C6(H6A,H6B,H6C), C35(H35A,H35B,H35C)
;
_shelx_res_checksum              5309
_olex2_submission_special_instructions 'No special instructions were received'