Atmospheric oxygen mediated oxidation coupling of primary and secondary alcohols: synthesis of pyrazolo[1,5-<i>a</i>]pyrimidines.
Guo, Xiaoshuang; Zhao, Peng; Jiang, Chengjun; Ma, Yongmin; Miao, Maozhong; Organic & biomolecular chemistry 23 (2025) 2092–2095; doi:10.1039/d4ob02045f

data_7160344
_publ_section_title
;
 Atmospheric oxygen mediated oxidation coupling of primary and secondary
 alcohols: synthesis of pyrazolo[1,5-<i>a</i>]pyrimidines.
;
_journal_issue                   9
_journal_name_full               'Organic &amp; biomolecular chemistry'
_journal_page_first              2092
_journal_page_last               2095
_journal_paper_doi               10.1039/d4ob02045f
_journal_volume                  23
_journal_year                    2025
_chemical_formula_moiety         'C16 H14 F3 N3'
_chemical_formula_sum            'C16 H14 F3 N3'
_chemical_formula_weight         305.30
_space_group_crystal_system      monoclinic
_space_group_IT_number           15
_space_group_name_Hall           '-C 2yc'
_space_group_name_H-M_alt        'C 1 2/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2023-08-26
_audit_creation_method
;
Olex2 1.5
(compiled 2021.11.18 svn.ra9532c28 for OlexSys, GUI svn.r6427)
;
_audit_update_record
;
2024-12-04 deposited with the CCDC.	2025-01-21 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 124.81(5)
_cell_angle_gamma                90
_cell_formula_units_Z            16
_cell_length_a                   26.52(5)
_cell_length_b                   17.03(3)
_cell_length_c                   15.65(4)
_cell_measurement_reflns_used    220
_cell_measurement_temperature    296.15
_cell_measurement_theta_max      21.456
_cell_measurement_theta_min      2.995
_cell_volume                     5803(2)
_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  (Sheldrick, 2015)'
_diffrn_ambient_temperature      296.15
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.937
_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  0.0541
_diffrn_reflns_av_unetI/netI     0.0402
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.937
_diffrn_reflns_limit_h_max       37
_diffrn_reflns_limit_h_min       -34
_diffrn_reflns_limit_k_max       23
_diffrn_reflns_limit_k_min       -23
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_number            56879
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.937
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         30.398
_diffrn_reflns_theta_min         1.518
_diffrn_source_current           30.0
_diffrn_source_power             1.35
_diffrn_source_voltage           45.0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.112
_exptl_absorpt_correction_T_max  1.0000
_exptl_absorpt_correction_T_min  0.8658
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.0564 before and 0.0463 after correction.
The Ratio of minimum to maximum transmission is 0.8658.
The \l/2 correction factor is 0.00150.
;
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.398
_exptl_crystal_description       block
_exptl_crystal_F_000             2528
_exptl_crystal_size_max          0.15
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.12
_refine_diff_density_max         0.237
_refine_diff_density_min         -0.215
_refine_diff_density_rms         0.034
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.016
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     427
_refine_ls_number_reflns         8229
_refine_ls_number_restraints     3
_refine_ls_restrained_S_all      1.018
_refine_ls_R_factor_all          0.1021
_refine_ls_R_factor_gt           0.0513
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0592P)^2^+2.3117P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1230
_refine_ls_wR_factor_ref         0.1485
_reflns_Friedel_coverage         0.000
_reflns_number_gt                4743
_reflns_number_total             8229
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d4ob02045f2.cif
_cod_data_source_block           mo230825a
_cod_depositor_comments          'Adding full bibliography for 7160344.cif.'
_cod_original_cell_volume        5803(21)
_cod_database_code               7160344
_shelx_shelxl_version_number     2018/3
_shelx_estimated_absorpt_t_max   0.987
_shelx_estimated_absorpt_t_min   0.983
_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. Restrained distances
 F7-C32 \\sim F9-C32
 with sigma of 0.02
 F5-C32 \\sim F8-C32
 with sigma of 0.02
 F4-C32 \\sim F00F-C32
 with sigma of 0.02
3. Others
 Sof(F00F)=Sof(F8)=Sof(F9)=1-FVAR(1)
 Sof(F4)=Sof(F5)=Sof(F7)=FVAR(1)
4.a Secondary CH2 refined with riding coordinates:
 C29(H29A,H29B), C30(H30A,H30B), C13(H13a,H13b), C14(H14a,H14b)
4.b Aromatic/amide H refined with riding coordinates:
 C17(H17), C18(H18), C22(H22), C23(H23), C24(H24), C26(H26), C27(H27), C1(H1),
 C2(H2), C6(H6), C8(H8), C9(H9), C10(H10), C11(H11)
4.c Idealised Me refined as rotating group:
 C31(H31A,H31B,H31C), C15(H15a,H15b,H15c)
;
_shelx_res_checksum              19324
_olex2_submission_special_instructions 'No special instructions were received'