#------------------------------------------------------------------------------
#$Date: 2017-10-13 14:42:48 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201982 $
#$URL: file:///home/coder/svn-repositories/cod/cif/4/02/34/4023489.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/
#
# All data on this site have been placed in the public domain by the
# contributors.
#
data_4023489
loop_
_publ_author_name
'Young Tak Lee'
'Young Keun Chung'
_publ_section_title
;
 Silver(I)-Catalyzed Facile Synthesis of Pyrazoles
 From Propargyl N-Sulfonylhydrazones
;
_journal_name_full               'Journal of Organic Chemistry'
_journal_page_first              4698
_journal_page_last               4701
_journal_paper_doi               10.1021/jo800663g
_journal_volume                  73
_journal_year                    2008
_chemical_formula_sum            'C10 H12 N2 O2 S'
_chemical_formula_weight         224.28
_chemical_name_systematic
;
 ?
;
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 1 21/c 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                 112.576(2)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   7.5334(3)
_cell_length_b                   18.0992(10)
_cell_length_c                   8.4620(4)
_cell_measurement_reflns_used    3857
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      27.485
_cell_measurement_theta_min      0.998
_cell_volume                     1065.37(9)
_computing_cell_refinement       'HKL Scalepack (Otwinowski & Minor 1997)'
_computing_data_collection       'Collect (Bruker AXS BV, 1997-2004)'
_computing_data_reduction
'HKL Denzo and Scalepack (Otwinowski & Minor 1997)'
_computing_molecular_graphics    ORTEP3
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      293(2)
_diffrn_detector_area_resol_mean 9
_diffrn_measured_fraction_theta_full 0.991
_diffrn_measured_fraction_theta_max 0.991
_diffrn_measurement_device_type  KappaCCD
_diffrn_measurement_method       CCD
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0171
_diffrn_reflns_av_sigmaI/netI    0.0284
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       23
_diffrn_reflns_limit_k_min       -21
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_number            4156
_diffrn_reflns_theta_full        27.47
_diffrn_reflns_theta_max         27.47
_diffrn_reflns_theta_min         2.84
_exptl_absorpt_coefficient_mu    0.285
_exptl_absorpt_correction_T_max  0.9194
_exptl_absorpt_correction_T_min  0.9194
_exptl_absorpt_correction_type   empirical
_exptl_absorpt_process_details
'R. H. Blessing, Acta Crystallogr., Sect A 1995, 51, 33-38.'
_exptl_crystal_colour            Colorless
_exptl_crystal_density_diffrn    1.398
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             472
_exptl_crystal_size_max          0.30
_exptl_crystal_size_mid          0.30
_exptl_crystal_size_min          0.30
_refine_diff_density_max         0.274
_refine_diff_density_min         -0.347
_refine_diff_density_rms         0.048
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.047
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     136
_refine_ls_number_reflns         2421
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.047
_refine_ls_R_factor_all          0.0509
_refine_ls_R_factor_gt           0.0413
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0554P)²+0.3594P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1093
_refine_ls_wR_factor_ref         0.1153
_reflns_number_gt                2027
_reflns_number_total             2421
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jo800663g-File004.cif
_cod_data_source_block           yt6
_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 2.4.1 from
2010-06-29.

'_exptl_absorpt_correction_type' value 'Empirical' changed to
'empirical' according to
'/home/saulius/struct/CIF-dictionaries/cif_core.dic' dictionary named
'cif_core.dic' version 2.4.1 from 2010-06-29.

Automatic conversion script
Id: cif_fix_enum 1527 2010-12-29 10:47:43Z saulius 
;
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               4023489
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
S1 S 0.23858(6) 0.65717(3) 0.61724(6) 0.04385(16) Uani 1 1 d . . .
N1 N 0.0214(2) 0.69488(8) 0.53918(17) 0.0397(3) Uani 1 1 d . . .
C5 C 0.2472(2) 0.59730(9) 0.7830(2) 0.0361(4) Uani 1 1 d . . .
O2 O 0.2584(2) 0.61500(10) 0.48255(19) 0.0679(5) Uani 1 1 d . . .
O1 O 0.36403(19) 0.71831(8) 0.6895(2) 0.0615(4) Uani 1 1 d . . .
C6 C 0.2903(3) 0.62539(10) 0.9467(2) 0.0432(4) Uani 1 1 d . . .
H6 H 0.3181 0.6753 0.9693 0.052 Uiso 1 1 calc R . .
C4 C 0.2078(3) 0.52262(10) 0.7492(2) 0.0435(4) Uani 1 1 d . . .
H4 H 0.1783 0.5041 0.6396 0.052 Uiso 1 1 calc R . .
N2 N -0.1299(2) 0.64315(10) 0.4682(2) 0.0522(4) Uani 1 1 d . . .
C2 C 0.2547(2) 0.50286(11) 1.0451(2) 0.0451(4) Uani 1 1 d . . .
C8 C -0.0330(3) 0.74890(11) 0.6441(3) 0.0529(5) Uani 1 1 d . . .
H8A H 0.0109 0.7982 0.6326 0.063 Uiso 1 1 calc R . .
H8B H 0.0184 0.7350 0.7640 0.063 Uiso 1 1 calc R . .
C7 C 0.2914(3) 0.57807(12) 1.0756(2) 0.0468(4) Uani 1 1 d . . .
H7 H 0.3171 0.5968 1.1845 0.056 Uiso 1 1 calc R . .
C1 C 0.2595(3) 0.45194(15) 1.1884(3) 0.0674(7) Uani 1 1 d . . .
H1A H 0.2310 0.4024 1.1455 0.101 Uiso 1 1 calc R . .
H1B H 0.1656 0.4678 1.2322 0.101 Uiso 1 1 calc R . .
H1C H 0.3850 0.4533 1.2784 0.101 Uiso 1 1 calc R . .
C3 C 0.2131(3) 0.47636(11) 0.8808(3) 0.0498(5) Uani 1 1 d . . .
H3 H 0.1882 0.4263 0.8588 0.060 Uiso 1 1 calc R . .
C9 C -0.2498(3) 0.74408(14) 0.5677(3) 0.0608(6) Uani 1 1 d . . .
H9A H -0.3032 0.7454 0.6553 0.073 Uiso 1 1 calc R . .
H9B H -0.3062 0.7833 0.4856 0.073 Uiso 1 1 calc R . .
C10 C -0.2772(3) 0.67107(13) 0.4836(3) 0.0588(5) Uani 1 1 d . . .
H10 H -0.3952 0.6470 0.4443 0.071 Uiso 1 1 calc R . .
loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
S1 0.0448(3) 0.0495(3) 0.0449(3) 0.01103(19) 0.0256(2) 0.00704(19)
N1 0.0436(8) 0.0412(8) 0.0361(7) 0.0023(6) 0.0171(6) 0.0023(6)
C5 0.0346(8) 0.0390(8) 0.0365(8) 0.0030(7) 0.0156(6) 0.0027(7)
O2 0.0873(11) 0.0812(11) 0.0539(8) 0.0140(8) 0.0480(8) 0.0303(9)
O1 0.0458(7) 0.0602(9) 0.0787(10) 0.0200(8) 0.0242(7) -0.0080(7)
C6 0.0443(9) 0.0420(9) 0.0410(9) -0.0030(8) 0.0138(7) -0.0023(8)
C4 0.0494(10) 0.0405(9) 0.0422(9) -0.0022(7) 0.0193(8) 0.0033(8)
N2 0.0540(10) 0.0517(9) 0.0401(8) -0.0068(7) 0.0062(7) -0.0042(8)
C2 0.0372(9) 0.0522(11) 0.0479(10) 0.0154(9) 0.0184(7) 0.0090(8)
C8 0.0498(11) 0.0498(11) 0.0567(11) -0.0125(9) 0.0179(9) 0.0054(9)
C7 0.0456(10) 0.0607(12) 0.0326(8) -0.0002(8) 0.0132(7) 0.0022(9)
C1 0.0600(13) 0.0787(16) 0.0688(14) 0.0356(13) 0.0307(11) 0.0193(11)
C3 0.0534(11) 0.0374(9) 0.0603(12) 0.0038(8) 0.0237(9) 0.0024(8)
C9 0.0497(11) 0.0738(15) 0.0614(12) 0.0011(11) 0.0240(10) 0.0107(10)
C10 0.0420(10) 0.0716(14) 0.0541(12) 0.0033(10) 0.0087(9) -0.0085(10)
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
O2 S1 O1 120.04(10) . . ?
O2 S1 N1 106.97(8) . . ?
O1 S1 N1 103.92(8) . . ?
O2 S1 C5 109.00(9) . . ?
O1 S1 C5 108.69(9) . . ?
N1 S1 C5 107.50(7) . . ?
N2 N1 C8 109.09(14) . . ?
N2 N1 S1 114.01(12) . . ?
C8 N1 S1 119.41(12) . . ?
C4 C5 C6 120.65(16) . . ?
C4 C5 S1 119.78(13) . . ?
C6 C5 S1 119.56(14) . . ?
C7 C6 C5 119.11(17) . . ?
C3 C4 C5 119.07(17) . . ?
C10 N2 N1 106.61(17) . . ?
C3 C2 C7 118.41(16) . . ?
C3 C2 C1 121.27(19) . . ?
C7 C2 C1 120.32(19) . . ?
N1 C8 C9 102.01(16) . . ?
C6 C7 C2 121.19(17) . . ?
C4 C3 C2 121.55(18) . . ?
C10 C9 C8 100.71(17) . . ?
N2 C10 C9 116.06(18) . . ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
S1 O2 1.4264(15) . ?
S1 O1 1.4311(16) . ?
S1 N1 1.6578(15) . ?
S1 C5 1.7541(17) . ?
N1 N2 1.418(2) . ?
N1 C8 1.480(2) . ?
C5 C4 1.390(3) . ?
C5 C6 1.392(2) . ?
C6 C7 1.384(3) . ?
C4 C3 1.381(3) . ?
N2 C10 1.270(3) . ?
C2 C3 1.388(3) . ?
C2 C7 1.393(3) . ?
C2 C1 1.513(3) . ?
C8 C9 1.511(3) . ?
C9 C10 1.477(3) . ?
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 30658690
