One-pot, two-step conversion of aldehydes to phosphonyl- and sulfonylpyrazoles using Bestmann-Ohira reagent
Kumar, Rahul; Verma, Deepti; Mobin, Shaikh M.; Namboothiri, Irishi N. N.; Organic Letters 14 (2012) 4070–4073; doi:10.1021/ol301695e

data_1508329
_publ_section_title
;
 One-pot, two-step conversion of aldehydes to phosphonyl- and
 sulfonylpyrazoles using Bestmann-Ohira reagent
;
_journal_coden_ASTM              ORLEF7
_journal_issue                   16
_journal_name_full               'Organic Letters'
_journal_page_first              4070
_journal_page_last               4073
_journal_paper_doi               10.1021/ol301695e
_journal_volume                  14
_journal_year                    2012
_chemical_formula_sum            'C13 H17 N2 O3 P'
_chemical_formula_weight         280.25
_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_creation_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 90.31(2)
_cell_angle_gamma                90.00
_cell_formula_units_Z            8
_cell_length_a                   15.927(4)
_cell_length_b                   10.8801(17)
_cell_length_c                   17.331(4)
_cell_measurement_reflns_used    2561
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      30.4397
_cell_measurement_theta_min      3.2647
_cell_volume                     3003.2(11)
_computing_cell_refinement       'CrysAlis RED, Oxford Diffraction Ltd.,'
_computing_data_collection       'CrysAlis CCD, Oxford Diffraction Ltd.,'
_computing_data_reduction        'CrysAlis RED, Oxford Diffraction Ltd.,'
_computing_molecular_graphics    Ortep3
_computing_publication_material  Shelx97
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1997)'
_diffrn_ambient_temperature      293(2)
_diffrn_detector_area_resol_mean 15.9948
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device_type  'OXFORD DIFFRACTION XCALIBUR-S'
_diffrn_measurement_method       \w/q-scan
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'Enhance (Mo) X-ray Source'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0995
_diffrn_reflns_av_sigmaI/netI    0.1701
_diffrn_reflns_limit_h_max       18
_diffrn_reflns_limit_h_min       -18
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            22001
_diffrn_reflns_theta_full        25.00
_diffrn_reflns_theta_max         25.00
_diffrn_reflns_theta_min         3.27
_exptl_absorpt_coefficient_mu    0.188
_exptl_absorpt_correction_T_max  0.9723
_exptl_absorpt_correction_T_min  0.9580
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlis RED, Oxford Diffraction Ltd.,
Version 1.171.31.7 (release 18-10-2006 CrysAlis171 .NET)
(compiled Oct 18 2006,16:28:17)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.240
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             1184
_exptl_crystal_size_max          0.23
_exptl_crystal_size_mid          0.19
_exptl_crystal_size_min          0.15
_refine_diff_density_max         0.184
_refine_diff_density_min         -0.170
_refine_diff_density_rms         0.031
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.686
_refine_ls_hydrogen_treatment    riding
_refine_ls_matrix_type           full
_refine_ls_number_parameters     347
_refine_ls_number_reflns         5261
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.686
_refine_ls_R_factor_all          0.1633
_refine_ls_R_factor_gt           0.0433
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0311P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0715
_refine_ls_wR_factor_ref         0.0867
_reflns_number_gt                1772
_reflns_number_total             5261
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ol301695e_si_003.cif
_cod_data_source_block           inn043
_cod_depositor_comments
;
The following automatic conversions were performed:

'_symmetry_cell_setting' value 'Monoclinic' changed to 'monoclinic'
according to /home/saulius/struct/CIF-dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.2 from 2011-04-26.

Automatic conversion script
Id: cif_fix_values 1891 2012-01-12 08:04:46Z andrius 

 Updated bibliographic information.

 Antanas Vaitkus,
 2019-09-20
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_cod_original_sg_symbol_H-M      'P 21/n'
_cod_database_code               1508329