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_7245865
_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         'C31 H28 N6 O'
_chemical_formula_sum            'C31 H28 N6 O'
_chemical_formula_weight         500.59
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_block_doi                 10.5517/ccdc.csd.cc2cyk96
_audit_creation_date             2022-08-11
_audit_creation_method
;
Olex2 1.5
(compiled 2022.04.07 svn.rca3783a0 for OlexSys, GUI svn.r6498)
;
_audit_update_record
;
2022-08-23 deposited with the CCDC.	2022-11-03 downloaded from the CCDC.
;
_cell_angle_alpha                101.682(5)
_cell_angle_beta                 92.413(5)
_cell_angle_gamma                114.101(5)
_cell_formula_units_Z            2
_cell_length_a                   8.156(2)
_cell_length_b                   9.356(2)
_cell_length_c                   19.728(5)
_cell_measurement_reflns_used    4363
_cell_measurement_temperature    294.94
_cell_measurement_theta_max      26.140
_cell_measurement_theta_min      2.808
_cell_volume                     1332.5(6)
_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 2019/2 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_diffrn_ambient_temperature      294.94
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.995
_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  0.0706
_diffrn_reflns_av_unetI/netI     0.0522
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.995
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       24
_diffrn_reflns_limit_l_min       -24
_diffrn_reflns_number            25207
_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.995
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.532
_diffrn_reflns_theta_min         2.808
_diffrn_source_current           30.0
_diffrn_source_power             1.5
_diffrn_source_voltage           50.0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.079
_exptl_absorpt_correction_T_max  0.7454
_exptl_absorpt_correction_T_min  0.6337
_exptl_absorpt_correction_type   numerical
_exptl_absorpt_process_details
;
SADABS-2016/2 (Bruker,2016) was used for absorption correction.
wR2(int) was 0.0713 before and 0.0598 after correction.
The Ratio of minimum to maximum transmission is 0.8501.
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    1.248
_exptl_crystal_description       block
_exptl_crystal_F_000             528
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.14
_exptl_crystal_size_min          0.1
_refine_diff_density_max         0.261
_refine_diff_density_min         -0.267
_refine_diff_density_rms         0.055
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.014
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     376
_refine_ls_number_reflns         5509
_refine_ls_number_restraints     3
_refine_ls_restrained_S_all      1.014
_refine_ls_R_factor_all          0.1508
_refine_ls_R_factor_gt           0.0797
_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^)+(0.1051P)^2^+1.2114P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2034
_refine_ls_wR_factor_ref         0.2631
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2842
_reflns_number_total             5509
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d2ra05532e2.cif
_cod_data_source_block           mg_al382_296k
_cod_original_cell_volume        1332.6(6)
_cod_database_code               7245865
_shelx_shelxl_version_number     2019/2
_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. Rigid body (RIGU) restrains
 O25, C26, C27, O1, C5, C21
 with sigma for 1-2 distances of 0.00002 and sigma for 1-3 distances of 0.00002
3. Same fragment restrains
{O1, C5, C21} sigma for 1-2: 0.02, 1-3: 0.02
as in
{O25, C26, C27}
4. Others
 Sof(O1)=Sof(C5)=Sof(H5A)=Sof(H5B)=Sof(C21)=Sof(H21A)=Sof(H21B)=Sof(H21C)=1-
 FVAR(1)
 Sof(O25)=Sof(C26)=Sof(H26A)=Sof(H26B)=Sof(C27)=Sof(H27A)=Sof(H27B)=Sof(H27C)=
 FVAR(1)
5.a Secondary CH2 refined with riding coordinates:
 C17(H17A,H17B), C18(H18A,H18B), C26(H26A,H26B), C5(H5A,H5B)
5.b Aromatic/amide H refined with riding coordinates:
 C11(H11), C12(H12), C13(H13), C14(H14), C15(H15), C16(H16), C31(H31),
 C32(H32), C34(H34), C35(H35)
5.c Idealised Me refined as rotating group:
 C6(H6A,H6B,H6C), C37(H37A,H37B,H37C), C38(H38A,H38B,H38C), C27(H27A,H27B,
 H27C), C21(H21A,H21B,H21C)
;
_shelx_res_checksum              90305
_olex2_submission_special_instructions 'No special instructions were received'