Pyrazole synthesis via a cascade Sonogashira coupling/cyclization of N-propargyl sulfonylhydrazones.
Yang, Ying; Hu, Zi-Lin; Li, Ren-Hao; Chen, Yi-Hui; Zhan, Zhuang-Ping; Organic & biomolecular chemistry 16 (2018) 197–201; doi:10.1039/c7ob02576a

data_7156001
_publ_section_title
;
 Pyrazole synthesis via a cascade Sonogashira coupling/cyclization of
 N-propargyl sulfonylhydrazones.
;
_journal_issue                   2
_journal_name_full               'Organic &amp; biomolecular chemistry'
_journal_page_first              197
_journal_page_last               201
_journal_paper_doi               10.1039/c7ob02576a
_journal_volume                  16
_journal_year                    2018
_chemical_formula_moiety         'C24 H18 N4 O4 S'
_chemical_formula_sum            'C24 H18 N4 O4 S'
_chemical_formula_weight         458.48
_chemical_melting_point          404.5(15)
_chemical_name_systematic
2-((3-(4-nitrophenyl)-1-tosyl-1H-pyrazol-4-yl)methyl)benzonitrile
_space_group_crystal_system      monoclinic
_space_group_IT_number           7
_space_group_name_Hall           'P -2yc'
_space_group_name_H-M_alt        'P 1 c 1'
_symmetry_space_group_name_Hall  'P -2yc'
_symmetry_space_group_name_H-M   'P 1 c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     iterative
_audit_creation_date             2016-06-20
_audit_creation_method
;
Olex2 1.2
(compiled 2016.02.19 svn.r3266 for OlexSys, GUI svn.r5155)
;
_audit_update_record
;
2017-10-18 deposited with the CCDC.
2017-11-29 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 98.158(5)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   7.966(2)
_cell_length_b                   9.708(3)
_cell_length_c                   13.669(4)
_cell_measurement_reflns_used    3465
_cell_measurement_temperature    203
_cell_measurement_theta_max      26.654
_cell_measurement_theta_min      2.582
_cell_volume                     1046.4(5)
_computing_cell_refinement       'SAINT v6.28A (Bruker, 2002)'
_computing_data_reduction        'SAINT v6.28A (Bruker, 2002)'
_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
;
Superflip (Palatinus & Chapuis, 2007;Palatinus & van der Lee, 2008;
Palatinus et al., 2012)
;
_diffrn_ambient_temperature      203
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.990
_diffrn_measurement_device_type  'Xcalibur, Sapphire3, Gemini ultra'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0277
_diffrn_reflns_av_unetI/netI     0.0493
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.990
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            8979
_diffrn_reflns_point_group_measured_fraction_full 0.973
_diffrn_reflns_point_group_measured_fraction_max 0.940
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.789
_diffrn_reflns_theta_min         2.098
_exptl_absorpt_coefficient_mu    0.196
_exptl_absorpt_correction_T_max  1.0000
_exptl_absorpt_correction_T_min  0.915174
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS v.2.03 (Bruker,200?) was used for absorption correction.
R(int) was 0.0830 before and 0.0415 after correction.
The Ratio of minimum to maximum transmission is 0.9152.
The \l/2 correction factor is 0.0015.
;
_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    1.455
_exptl_crystal_description       block
_exptl_crystal_F_000             476
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.1
_refine_diff_density_max         0.246
_refine_diff_density_min         -0.233
_refine_diff_density_rms         0.045
_refine_ls_abs_structure_details
;
 Flack x determined using 1726 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.03(4)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.042
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     299
_refine_ls_number_reflns         4646
_refine_ls_number_restraints     2
_refine_ls_restrained_S_all      1.041
_refine_ls_R_factor_all          0.0468
_refine_ls_R_factor_gt           0.0423
_refine_ls_shift/su_max          0.004
_refine_ls_shift/su_mean         0.001
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0510P)^2^+0.0080P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0966
_refine_ls_wR_factor_ref         0.0990
_reflns_Friedel_coverage         0.896
_reflns_Friedel_fraction_full    0.947
_reflns_Friedel_fraction_max     0.890
_reflns_number_gt                4247
_reflns_number_total             4646
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c7ob02576a2.cif
_cod_data_source_block           sad
_cod_depositor_comments
;
The following automatic conversions were performed:

'_chemical_melting_point' value '403-406' was changed to '404.5(15)'
- the average value was taken and precision was estimated.

Automatic conversion script
Id: cif_fix_values 4973 2017-02-22 13:04:09Z antanas 

 Adding full bibliography for 7156001.cif.
;
_cod_database_code               7156001
_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:
 C10(H10A,H10B)
2.b Aromatic/amide H refined with riding coordinates:
 C1(H1), C19(H19), C5(H5), C8(H8), C24(H24), C6(H6), C12(H12), C9(H9),
 C13(H13), C15(H15), C14(H14), C23(H23), C20(H20)
2.c Idealised Me refined as rotating group:
 C22(H22A,H22B,H22C)
;
_shelx_shelxl_version_number     2014/7
_olex2_submission_special_instructions 'No special instructions were received'