Comprehensive analysis of crystal structure, spectroscopic properties, quantum chemical insights, and molecular docking studies of two pyrazolopyridine compounds: potential anticancer agents
Polo-Cuadrado, Efraín; López-Cuellar, Lorena; Acosta-Quiroga, Karen; Rojas-Peña, Cristian; Brito, Iván; Cisterna, Jonathan; Trilleras, Jorge; Alderete, Joel B.; Duarte, Yorley; Gutiérrez, Margarita; RSC Advances 13 (2023) 30118–30128; doi:10.1039/D3RA04874H

data_7247519
_publ_section_title
;
 Comprehensive analysis of crystal structure, spectroscopic properties,
 quantum chemical insights, and molecular docking studies of two
 pyrazolopyridine compounds: potential anticancer agents
;
_journal_issue                   43
_journal_name_full               'RSC Advances'
_journal_page_first              30118
_journal_page_last               30128
_journal_paper_doi               10.1039/D3RA04874H
_journal_volume                  13
_journal_year                    2023
_chemical_formula_moiety         'C24 H22 N4 O'
_chemical_formula_sum            'C24 H22 N4 O'
_chemical_formula_weight         382.45
_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   mixed
_atom_sites_solution_primary     dual
_audit_block_doi                 10.5517/ccdc.csd.cc2ghh4m
_audit_creation_date             2020-11-05
_audit_creation_method
;
Olex2 1.3-alpha
(compiled 2020.10.28 svn.r5b043f8a for OlexSys, GUI svn.r6176)
;
_audit_update_record
;
2023-07-03 deposited with the CCDC.	2023-09-25 downloaded from the CCDC.
;
_cell_angle_alpha                71.974(2)
_cell_angle_beta                 74.329(3)
_cell_angle_gamma                89.987(3)
_cell_formula_units_Z            2
_cell_length_a                   8.0100(9)
_cell_length_b                   9.8032(11)
_cell_length_c                   13.6657(15)
_cell_measurement_reflns_used    8543
_cell_measurement_temperature    295.2
_cell_measurement_theta_max      30.468
_cell_measurement_theta_min      3.594
_cell_volume                     978.40(19)
_computing_cell_refinement       'SAINT v8.37A (Bruker, 2015)'
_computing_data_reduction        'SAINT v8.37A (Bruker, 2015)'
_computing_molecular_graphics    'Olex2 1.3-alpha (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3-alpha (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL  (Sheldrick, 2008)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_diffrn_ambient_temperature      295.2
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.991
_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  0.0406
_diffrn_reflns_av_unetI/netI     0.0293
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.991
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            27838
_diffrn_reflns_point_group_measured_fraction_full 0.996
_diffrn_reflns_point_group_measured_fraction_max 0.991
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         30.645
_diffrn_reflns_theta_min         3.594
_diffrn_source_current           30.0
_diffrn_source_power             1.5
_diffrn_source_voltage           50.0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.082
_exptl_absorpt_correction_T_max  0.7461
_exptl_absorpt_correction_T_min  0.6833
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.0611 before and 0.0480 after correction.
The Ratio of minimum to maximum transmission is 0.9158.
The \l/2 correction factor is Not present.
;
_exptl_crystal_colour            'light yellow'
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.298
_exptl_crystal_description       block
_exptl_crystal_F_000             404
_exptl_crystal_size_max          0.718
_exptl_crystal_size_mid          0.67
_exptl_crystal_size_min          0.504
_refine_diff_density_max         0.300
_refine_diff_density_min         -0.240
_refine_diff_density_rms         0.052
_refine_ls_extinction_coef       0.036(4)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2016/6 (Sheldrick 2016)'
_refine_ls_goodness_of_fit_ref   1.060
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     282
_refine_ls_number_reflns         5989
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.060
_refine_ls_R_factor_all          0.1031
_refine_ls_R_factor_gt           0.0595
_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^)+(0.0527P)^2^+0.7372P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1349
_refine_ls_wR_factor_ref         0.1733
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3954
_reflns_number_total             5989
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d3ra04874h2.cif
_cod_data_source_block           mg_al503_296k
_cod_database_code               7247519
_shelx_shelxl_version_number     2016/6
_shelx_estimated_absorpt_t_max   0.960
_shelx_estimated_absorpt_t_min   0.944
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C00H(H00H), C00J(H00J), C00M(H00M), C00O(H00O), C12(H12), C13(H13), C14(H14),
 C15(H15), C16(H16)
2.b Idealised Me refined as rotating group:
 C00Q(H00A,H00B,H00C), C00T(H00D,H00E,H00F), C6(H6A,H6B,H6C)
;
_shelx_res_checksum              98831
_olex2_submission_special_instructions 'No special instructions were received'