Divergent synthesis of 3-formylpyrazolo[1,5-<i>a</i>]pyrimidines and methylene-bridged bis(pyrazolo[1,5-<i>a</i>]pyrimidines) using DMSO as a single carbon synthon.
Sikdar, Papiya; Das, Sourav; Saini, Sheetal; Sawant, Sanghapal D.; Bagdi, Avik Kumar; Organic & biomolecular chemistry 23 (2025) 7566–7570; doi:10.1039/d5ob01042j

data_7160652
_publ_section_title
;
 Divergent synthesis of 3-formylpyrazolo[1,5-<i>a</i>]pyrimidines and
 methylene-bridged bis(pyrazolo[1,5-<i>a</i>]pyrimidines) using DMSO as a
 single carbon synthon.
;
_journal_issue                   33
_journal_name_full               'Organic &amp; biomolecular chemistry'
_journal_page_first              7566
_journal_page_last               7570
_journal_paper_doi               10.1039/d5ob01042j
_journal_volume                  23
_journal_year                    2025
_chemical_formula_moiety         'C20 H15 N3 O'
_chemical_formula_sum            'C20 H15 N3 O'
_chemical_formula_weight         313.35
_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   geom
_audit_update_record
;
2025-05-15 deposited with the CCDC.	2025-07-29 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 101.025(2)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   12.9831(9)
_cell_length_b                   7.4371(5)
_cell_length_c                   16.6855(12)
_cell_measurement_reflns_used    9948
_cell_measurement_temperature    299.(2)
_cell_measurement_theta_max      24.2592
_cell_measurement_theta_min      2.4872
_cell_volume                     1581.36(19)
_computing_cell_refinement       'SAINT V8.40B (Bruker AXS LLC, 2019)'
_computing_data_reduction        'SAINT V8.40B (Bruker AXS LLC, 2019)'
_computing_structure_refinement  'SHELXL-2019/1 (Sheldrick, 2019)'
_computing_structure_solution    'XT, VERSION 2018/2'
_diffrn_ambient_temperature      299.(2)
_diffrn_detector_area_resol_mean 7.3910
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measurement_device_type  Bruker
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0849
_diffrn_reflns_av_unetI/netI     0.0406
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            58971
_diffrn_reflns_theta_full        25.02
_diffrn_reflns_theta_max         25.02
_diffrn_reflns_theta_min         2.49
_exptl_absorpt_coefficient_mu    0.084
_exptl_absorpt_correction_T_max  0.7452
_exptl_absorpt_correction_T_min  0.655
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
Krause, L., Herbst-Irmer, R., Sheldrick, G. M., Stalke, D. (2015).
"Comparison of silver and molybdenum microfocus X-ray sources for
single-crystal structure determination"
J. Appl. Cryst. 48, 3-10.
doi:10.1107/S1600576714022985
;
_exptl_crystal_colour            Colorless
_exptl_crystal_density_diffrn    1.316
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       Block
_exptl_crystal_F_000             656
_refine_diff_density_max         0.223
_refine_diff_density_min         -0.221
_refine_ls_extinction_coef       0.024(3)
_refine_ls_extinction_method     'SHELXL-2019/1 (Sheldrick 2019)'
_refine_ls_goodness_of_fit_ref   1.135
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     219
_refine_ls_number_reflns         2786
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.135
_refine_ls_R_factor_all          0.1068
_refine_ls_R_factor_gt           0.0684
_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^)+(0.0327P)^2^+1.0629P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1221
_refine_ls_wR_factor_ref         0.1426
_reflns_Friedel_coverage         0.000
_reflns_number_gt                1911
_reflns_number_total             2786
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d5ob01042j2.cif
_cod_data_source_block           AKB_PS_770
_cod_depositor_comments
;
The following automatic conversions were performed:

data item '_exptl_absorpt_correction_type' value 'Multi-Scan' was
changed to 'multi-scan' in accordance with the
/home/data/users/saulius/crontab/automatic-downloads/rss-feeds/RSC/lib/dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.2 last updated on
2011-04-26.

Automatic conversion script
Id: cif_fix_values 8170 2020-07-09 18:12:32Z antanas 

 Adding full bibliography for 7160652.cif.
;
_cod_database_code               7160652
_olex2_refinement_description
;
1.a Aromatic/amide H refined with riding coordinates:
 C2(H2), C3(H3), C4(H4), C5(H5), C6(H6), C8(H8), C9(H9), C11(H11), C12(H12),
 C14(H14), C15(H15), C19(H19)
1.b Idealised Me refined as rotating group:
 C20(H20A,H20B,H20C)
;
_shelx_res_checksum              10488