Synthesis of pyrazolylvinyl ketones from furan derivatives.
Sawengngen, Nattawut; Chalikidi, Petrakis N.; Araby, Sara; Hampel, Frank; Gmeiner, Peter; Serdyuk, Olga V.; Organic & biomolecular chemistry 17 (2019) 4850–4855; doi:10.1039/c9ob00701f

data_7156817
_publ_section_title
;
 Synthesis of pyrazolylvinyl ketones from furan derivatives.
;
_journal_issue                   19
_journal_name_full               'Organic &amp; biomolecular chemistry'
_journal_page_first              4850
_journal_page_last               4855
_journal_paper_doi               10.1039/c9ob00701f
_journal_volume                  17
_journal_year                    2019
_chemical_formula_moiety         'C22 H21 F N2 O'
_chemical_formula_sum            'C22 H21 F N2 O'
_chemical_formula_weight         348.41
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_block_doi                 10.5517/ccdc.csd.cc2110vz
_audit_creation_date             2018-06-29
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_audit_update_record
;
2018-11-08 deposited with the CCDC.    2019-04-30 downloaded from the CCDC.
;
_cell_angle_alpha                79.991(8)
_cell_angle_beta                 78.903(8)
_cell_angle_gamma                89.752(7)
_cell_formula_units_Z            2
_cell_length_a                   7.4796(7)
_cell_length_b                   8.7825(8)
_cell_length_c                   14.3379(14)
_cell_measurement_reflns_used    1961
_cell_measurement_temperature    152(1)
_cell_measurement_theta_max      64.6080
_cell_measurement_theta_min      5.5700
_cell_volume                     909.76(15)
_computing_cell_refinement       'CrysAlisPro 1.171.38.46 (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.38.46 (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.46 (Rigaku OD, 2015)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      152(1)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 10.6144
_diffrn_detector_type            Atlas
_diffrn_measured_fraction_theta_full 0.892
_diffrn_measured_fraction_theta_max 0.946
_diffrn_measurement_details
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  t~exp~   \w     \q     \k     \f   Frames
  1  \w    -66.00  30.00   1.00    1.00    --  -42.06  38.00-120.00   96
  2  \w     37.00 114.00   1.00    1.00    --   88.61 -45.00-150.00   77
  3  \w     67.00 152.00   1.00    1.00    --   88.61  45.00-120.00   85
  4  \w     39.00 109.00   1.00    1.00    --   88.61 -94.00-120.00   70
  5  \w     11.00 138.00   1.00    1.00    --   88.61 -15.00  60.00  127
  6  \w    101.00 162.00   1.00    1.00    --   88.61 125.00 120.00   61
  7  \w     12.00 121.00   1.00    1.00    --   88.61 -77.00  90.00  109
  8  \w     25.00 121.00   1.00    1.00    --   88.61-125.00  90.00   96
  9  \w   -111.00 -18.00   1.00    1.00    --  -42.06 -38.00  60.00   93
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, Atlas'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.1892782000
_diffrn_orient_matrix_UB_12      0.0469902000
_diffrn_orient_matrix_UB_13      -0.0629756000
_diffrn_orient_matrix_UB_21      0.0505430000
_diffrn_orient_matrix_UB_22      0.0765430000
_diffrn_orient_matrix_UB_23      0.0806675000
_diffrn_orient_matrix_UB_31      0.0755947000
_diffrn_orient_matrix_UB_32      -0.1539156000
_diffrn_orient_matrix_UB_33      0.0435915000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0287
_diffrn_reflns_av_unetI/netI     0.0325
_diffrn_reflns_Laue_measured_fraction_full 0.892
_diffrn_reflns_Laue_measured_fraction_max 0.946
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            4868
_diffrn_reflns_point_group_measured_fraction_full 0.892
_diffrn_reflns_point_group_measured_fraction_max 0.946
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         64.818
_diffrn_reflns_theta_min         5.116
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.690
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.66351
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.38.46 (Rigaku Oxford Diffraction, 2015)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            'clear light colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.272
_exptl_crystal_description       block
_exptl_crystal_F_000             368
_exptl_crystal_recrystallization_method 'crystalizzed from CDCl3'
_exptl_crystal_size_max          0.312
_exptl_crystal_size_mid          0.259
_exptl_crystal_size_min          0.226
_refine_diff_density_max         0.190
_refine_diff_density_min         -0.308
_refine_diff_density_rms         0.052
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.036
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     236
_refine_ls_number_reflns         2931
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.036
_refine_ls_R_factor_all          0.0630
_refine_ls_R_factor_gt           0.0497
_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^)+(0.0838P)^2^+0.1321P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1258
_refine_ls_wR_factor_ref         0.1403
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2338
_reflns_number_total             2931
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c9ob00701f2.cif
_cod_data_source_block           18gme_os01
_cod_depositor_comments          'Adding full bibliography for 7156817.cif.'
_cod_database_code               7156817
_shelxl_version_number           2014/6
_chemical_oxdiff_formula         'C80 H14 N2 O F'
_reflns_odcompleteness_completeness 98.21
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     61.08
_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.a Secondary CH2 refined with riding coordinates:
 C4(H4A,H4B), C5(H5A,H5B), C6(H6A,H6B)
2.b Aromatic/amide H refined with riding coordinates:
 C1(H1), C2(H2), C14(H14), C22(H22), C23(H23), C24(H24), C25(H25), C26(H26),
 C32(H32), C33(H33), C35(H35), C36(H36)
2.c Idealised Me refined as rotating group:
 C7(H7A,H7B,H7C)
;
_olex2_date_sample_data_collection 2018-06-28
_olex2_exptl_crystal_mounting_method 'mounted on a loop'
_olex2_submission_original_sample_id OSG-II-2
_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.967
_oxdiff_exptl_absorpt_empirical_full_min 0.674