Vilsmeier reagent mediated synthesis of 6-[(formyloxy)methyl]-pyrazolopyrimidines via one-pot multiple tandem reaction
Lu, Shi-Han; Liu, Po-Lin; Wong, Fung Fuh; RSC Adv.  (2015) –; doi:10.1039/C5RA07707A

data_7220471
_publ_section_title
;
 Vilsmeier reagent mediated synthesis of
 6-[(formyloxy)methyl]-pyrazolopyrimidines via one-pot multiple tandem
 reaction
;
_journal_name_full               'RSC Adv.'
_journal_paper_doi               10.1039/C5RA07707A
_journal_year                    2015
_chemical_formula_sum            'C20 H16 N4 O3'
_chemical_formula_weight         360.37
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2yn'
_symmetry_space_group_name_H-M   'P 1 21/n 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_block_doi                 10.5517/cc13h4qg
_audit_creation_method           SHELXL-97
_audit_update_record
;
2014-10-03 deposited with the CCDC.
2015-05-13 downloaded from the CCDC.
;
_cell_angle_alpha                90.00
_cell_angle_beta                 98.900(2)
_cell_angle_gamma                90.00
_cell_formula_units_Z            8
_cell_length_a                   14.1926(3)
_cell_length_b                   7.2123(2)
_cell_length_c                   34.1402(8)
_cell_measurement_reflns_used    5434
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      64.1168
_cell_measurement_theta_min      3.2207
_cell_volume                     3452.56(15)
_computing_cell_refinement       'SAINT V7.68A (Bruker AXS, 2009)'
_computing_data_collection       'APEX2 (Bruker AXS, 2010)'
_computing_data_reduction        'SAINT V7.68A (Bruker AXS, 2009)'
_computing_molecular_graphics    'SHELXTL (Sheldrick, 2008)'
_computing_publication_material  SHELXTL
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      100(2)
_diffrn_detector_area_resol_mean 8.3333
_diffrn_measured_fraction_theta_full 0.952
_diffrn_measured_fraction_theta_max 0.952
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_monochromator  'montel mirror'
_diffrn_radiation_source         'microfocus tube'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0460
_diffrn_reflns_av_sigmaI/netI    0.0463
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -3
_diffrn_reflns_limit_l_max       40
_diffrn_reflns_limit_l_min       -40
_diffrn_reflns_number            18171
_diffrn_reflns_theta_full        65.78
_diffrn_reflns_theta_max         65.78
_diffrn_reflns_theta_min         3.22
_exptl_absorpt_coefficient_mu    0.791
_exptl_absorpt_correction_T_max  0.9492
_exptl_absorpt_correction_T_min  0.8180
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS V2008/1 (Bruker AXS)'
_exptl_crystal_colour            'Pale Orange'
_exptl_crystal_density_diffrn    1.387
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       Lump
_exptl_crystal_F_000             1504
_exptl_crystal_size_max          0.12
_exptl_crystal_size_mid          0.10
_exptl_crystal_size_min          0.10
_refine_diff_density_max         0.309
_refine_diff_density_min         -0.235
_refine_diff_density_rms         0.042
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.039
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     526
_refine_ls_number_reflns         5703
_refine_ls_number_restraints     111
_refine_ls_restrained_S_all      1.049
_refine_ls_R_factor_all          0.0978
_refine_ls_R_factor_gt           0.0586
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0669P)^2^+1.7956P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1431
_refine_ls_wR_factor_ref         0.1682
_reflns_number_gt                3550
_reflns_number_total             5703
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            c5ra07707a2.cif
_cod_data_source_block           130527
_cod_depositor_comments
;
The following automatic conversions were performed:

'_exptl_crystal_density_meas' value 'not measured' was changed to '?'
- the value is perceived as not measured.

Automatic conversion script
Id: cif_fix_values 3271 2015-04-21 07:52:19Z andrius 
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_cod_database_code               7220471