DABCO-promoted synthesis of pyrazoles from tosylhydrazones and nitroalkenes.
Tang, Meng; Zhang, Wen; Kong, Yuanfang; Organic & biomolecular chemistry 11 (2013) 6250–6254; doi:10.1039/c3ob41435c

data_7153079
_publ_section_title
;
 DABCO-promoted synthesis of pyrazoles from tosylhydrazones and
 nitroalkenes.
;
_journal_issue                   37
_journal_name_full               'Organic &amp; biomolecular chemistry'
_journal_page_first              6250
_journal_page_last               6254
_journal_paper_doi               10.1039/c3ob41435c
_journal_volume                  11
_journal_year                    2013
_chemical_formula_moiety         'C15 H12 N2'
_chemical_formula_sum            'C15 H12 N2'
_chemical_formula_weight         220.27
_chemical_name_systematic
;
 ? 
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           15
_space_group_name_Hall           '-C 2yc'
_space_group_name_H-M_alt        'C 1 2/c 1'
_symmetry_space_group_name_Hall  '-C 2yc'
_symmetry_space_group_name_H-M   'C 1 2/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     iterative
_atom_sites_solution_secondary   difmap
_audit_creation_date             2013-03-21
_audit_creation_method
;
  Olex2 1.2
  (compiled Dec  5 2012 16:20:19, GUI svn.r4385)
;
_cell_angle_alpha                90.00
_cell_angle_beta                 109.578(6)
_cell_angle_gamma                90.00
_cell_formula_units_Z            16
_cell_length_a                   16.9366(9)
_cell_length_b                   17.1465(7)
_cell_length_c                   17.6534(9)
_cell_measurement_reflns_used    2636
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      23.6850
_cell_measurement_theta_min      3.4800
_cell_volume                     4830.2(4)
_computing_cell_refinement
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.24 (release 03-12-2012 CrysAlis171 .NET)
(compiled Dec  3 2012,18:21:49)
;
_computing_data_collection
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.24 (release 03-12-2012 CrysAlis171 .NET)
(compiled Dec  3 2012,18:21:49)
;
_computing_data_reduction
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.24 (release 03-12-2012 CrysAlis171 .NET)
(compiled Dec  3 2012,18:21:49)
;
_computing_molecular_graphics
;
O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann,
OLEX2: a complete structure solution, refinement and analysis program.
J. Appl. Cryst. (2009). 42, 339-341.
;
_computing_publication_material
;
O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann,
OLEX2: a complete structure solution, refinement and analysis program.
J. Appl. Cryst. (2009). 42, 339-341.
;
_computing_structure_refinement
;
SHELXL, G.M. Sheldrick, Acta Cryst.
(2008). A64, 112-122
;
_computing_structure_solution
'SUPERFLIP, J. Appl. Cryst. (2007) 40, 786-790'
_diffrn_ambient_temperature      293(2)
_diffrn_detector_area_resol_mean 16.0733
_diffrn_measured_fraction_theta_full 0.9978
_diffrn_measured_fraction_theta_max 0.8893
_diffrn_measurement_details
;
  1 omega   40.00  101.20   1.2000   14.0000
omega____ theta____ kappa____ phi______ frames
    -       22.6512  178.0000   90.0000 51

  2 omega  -39.00   36.60   1.2000   14.0000
omega____ theta____ kappa____ phi______ frames
    -       22.6512  -38.0000   30.0000 63

  3 omega  -11.00   95.80   1.2000   14.0000
omega____ theta____ kappa____ phi______ frames
    -       22.6512   38.0000 -150.0000 89
;
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, Eos'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_UB_11      -0.0359713000
_diffrn_orient_matrix_UB_12      0.0228163000
_diffrn_orient_matrix_UB_13      -0.0034978000
_diffrn_orient_matrix_UB_21      -0.0130720000
_diffrn_orient_matrix_UB_22      -0.0280954000
_diffrn_orient_matrix_UB_23      0.0228174000
_diffrn_orient_matrix_UB_31      0.0225581000
_diffrn_orient_matrix_UB_32      0.0200300000
_diffrn_orient_matrix_UB_33      0.0359046000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.7107
_diffrn_reflns_av_R_equivalents  0.0286
_diffrn_reflns_av_unetI/netI     0.0469
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_h_min       -21
_diffrn_reflns_limit_k_max       21
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_number            10140
_diffrn_reflns_theta_full        25.50
_diffrn_reflns_theta_max         26.37
_diffrn_reflns_theta_min         3.34
_diffrn_source                   'SuperNova (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    0.073
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.84788
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.24 (release 03-12-2012 CrysAlis171 .NET)
(compiled Dec  3 2012,18:21:49)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            'clear light yellow'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.212
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             1856
_exptl_crystal_size_max          0.35
_exptl_crystal_size_mid          0.33
_exptl_crystal_size_min          0.28
_refine_diff_density_max         0.154
_refine_diff_density_min         -0.167
_refine_diff_density_rms         0.036
_refine_ls_extinction_coef       0.0018(2)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_ref   0.981
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     312
_refine_ls_number_reflns         4927
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      0.981
_refine_ls_R_factor_all          0.0932
_refine_ls_R_factor_gt           0.0552
_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^)+(0.0590P)^2^+2.1388P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1252
_refine_ls_wR_factor_ref         0.1504
_reflns_number_gt                3152
_reflns_number_total             4927
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            c3ob41435c.txt
_cod_data_source_block           tangmeng0320
_cod_database_code               7153079
_reflns_odcompleteness_completeness 99.78
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     26.32
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  H1 of N1, H2 of N2, H4 of N4, H20 of C20, H2A of C2, H3A of C3, H4A of C4,
  H5 of C5, H6 of C6, H8 of C8, H11 of C11, H12 of C12, H13 of C13, H14 of C14,
  H15 of C15, H17 of C17, H18 of C18, H19 of C19, H21 of C21, H23 of C23, H26
  of C26, H27 of C27, H28 of C28, H29 of C29, H30 of C30
2. Restrained distances
 H3-N3
 0.86 with sigma of 0.02
3. Others
 Fixed Sof: H1(0.5) H2(0.5) H4(0.5) H3(0.5)
4.a Aromatic/amide H refined with riding coordinates:
 N1(H1), N2(H2), N4(H4), C2(H2A), C3(H3A), C4(H4A), C5(H5), C6(H6), C8(H8),
 C11(H11), C12(H12), C13(H13), C14(H14), C15(H15), C17(H17), C18(H18), C19(H19),
  C20(H20), C21(H21), C23(H23), C26(H26), C27(H27), C28(H28), C29(H29), C30(H30)
;