Simple assembly of polysubstituted pyrazoles and isoxazoles via ring closure-ring opening domino reaction of 3-acyl-4,5-dihydrofurans with hydrazines and hydroxylamine.
Chagarovskiy, Alexey O.; Budynina, Ekaterina M.; Ivanova, Olga A.; Rybakov, Victor B.; Trushkov, Igor V.; Melnikov, Mikhail Ya; Organic & biomolecular chemistry 14 (2016) 2905–2915; doi:10.1039/c5ob02596f

data_7154959
_publ_section_title
;
 Simple assembly of polysubstituted pyrazoles and isoxazoles via ring
 closure-ring opening domino reaction of 3-acyl-4,5-dihydrofurans with
 hydrazines and hydroxylamine.
;
_journal_issue                   10
_journal_name_full               'Organic &amp; biomolecular chemistry'
_journal_page_first              2905
_journal_page_last               2915
_journal_paper_doi               10.1039/c5ob02596f
_journal_volume                  14
_journal_year                    2016
_chemical_formula_moiety         'C16 H21 N O5'
_chemical_formula_sum            'C16 H21 N O5'
_chemical_formula_weight         307.34
_chemical_melting_point_gt       394
_chemical_melting_point_lt       395
_chemical_name_systematic
; 
 2-(3,4,5-trimethoxyphenyl)-2-(3,5-dimethylpyrazol-4-yl)ethanol 
;
_space_group_IT_number           2
_symmetry_cell_setting           triclinic
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_block_doi                 10.5517/cc1kb917
_audit_update_record
;
2015-12-06 deposited with the CCDC.
2016-02-03 downloaded from the CCDC.
;
_cell_angle_alpha                65.488(3)
_cell_angle_beta                 72.568(3)
_cell_angle_gamma                72.725(3)
_cell_formula_units_Z            2
_cell_length_a                   7.7056(4)
_cell_length_b                   10.9002(4)
_cell_length_c                   11.0359(4)
_cell_measurement_reflns_used    14414
_cell_measurement_temperature    295(2)
_cell_measurement_theta_max      72.52
_cell_measurement_theta_min      4.49
_cell_volume                     788.58(6)
_computing_cell_refinement       '<i>X--AREA</i>  (STOE & CIE, 2012)'
_computing_data_collection       '<i>X--AREA</i>  (STOE & CIE, 2012)'
_computing_data_reduction        '<i>X--AREA</i>  (STOE & CIE, 2012)'
_computing_molecular_graphics    '<i>Ortep--3</i> (Farrugia,   1997)'
_computing_publication_material  '<i>WinGX</i>    (Farrugia,   1999)'
_computing_structure_refinement  '<i>SHELXL97</i> (Sheldrick,  2008)'
_computing_structure_solution    '<i>SHELXS97</i> (Sheldrick,  2008)'
_diffrn_ambient_temperature      295(2)
_diffrn_detector                 Pilatus100K
_diffrn_detector_area_resol_mean 5.81
_diffrn_detector_type            STOE
_diffrn_measured_fraction_theta_full 0.944
_diffrn_measured_fraction_theta_max 0.944
_diffrn_measurement_details      '3497 frames, detector distance = 60 mm'
_diffrn_measurement_device_type  'Stoe STADI VARI'
_diffrn_measurement_method       'rotation method'
_diffrn_radiation_collimation    'focusing mirrors'
_diffrn_radiation_monochromator  none
_diffrn_radiation_polarisn_norm  0
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54186
_diffrn_reflns_av_R_equivalents  0.0000
_diffrn_reflns_av_sigmaI/netI    0.0945
_diffrn_reflns_Laue_measured_fraction_full 0.944
_diffrn_reflns_Laue_measured_fraction_max 0.944
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       0
_diffrn_reflns_number            2690
_diffrn_reflns_point_group_measured_fraction_full 0.944
_diffrn_reflns_point_group_measured_fraction_max 0.944
_diffrn_reflns_theta_full        67.686
_diffrn_reflns_theta_max         67.689
_diffrn_reflns_theta_min         4.497
_diffrn_source                   'Cu GeniX 3D'
_diffrn_source_current           0.600
_diffrn_source_power             0.030
_diffrn_source_voltage           50
_exptl_absorpt_coefficient_mu    0.798
_exptl_absorpt_correction_T_max  0.9609
_exptl_absorpt_correction_T_min  0.4209
_exptl_absorpt_correction_type   refdelf
_exptl_absorpt_process_details
;
Walker, N. & Stuart, D (1983) Acta. Cryst. A39, 158-166
;
_exptl_crystal_colour            Colourless
_exptl_crystal_density_diffrn    1.294
_exptl_crystal_description       Prism
_exptl_crystal_F_000             328
_exptl_crystal_preparation       'petroleum ether : ethyl acetate, 1:2'
_exptl_crystal_size_max          0.100
_exptl_crystal_size_mid          0.100
_exptl_crystal_size_min          0.100
_refine_diff_density_max         0.189
_refine_diff_density_min         -0.203
_refine_diff_density_rms         0.051
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.960
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     208
_refine_ls_number_reflns         2690
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.960
_refine_ls_R_factor_all          0.0589
_refine_ls_R_factor_gt           0.0526
_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^)+(0.0887P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1207
_refine_ls_wR_factor_ref         0.1249
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2160
_reflns_number_total             2690
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c5ob02596f2.cif
_cod_data_source_block           ch6173i
_cod_depositor_comments
;
The following automatic conversions were performed:

'_symmetry_cell_setting' value 'Triclinic' changed to 'triclinic'
according to
/usr/data/users/saulius/crontab/automatic-downloads/rss-feeds/RSC/lib/dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.2 from 2011-04-26.

Automatic conversion script
Id: cif_fix_values 4268 2015-11-12 08:31:59Z antanas 

 Adding full bibliography for 7154959.cif.
;
_cod_database_code               7154959
_shelx_estimated_absorpt_t_min   0.924
_shelx_estimated_absorpt_t_max   0.924
_exptl_absorpt_factor_mur        0.040
_shelxl_version_number           2013-4
_shelx_res_checksum              24963