#------------------------------------------------------------------------------
#$Date: 2016-02-13 14:50:18 +0200 (Sat, 13 Feb 2016) $
#$Revision: 176428 $
#$URL: svn://www.crystallography.net/cod/cif/4/03/13/4031335.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_4031335
loop_
_publ_author_name
'Sun, Jun'
'Qiu, Jiang-Kai'
'Zhu, Yi-Long'
'Guo, Cheng'
'Hao, Wen-Juan'
'Jiang, Bo'
'Tu, Shu-Jiang'
_publ_section_title
;
 Metal-Free Iodine-Catalyzed Synthesis of Fully Substituted Pyrazoles and
 Its Sulphenylation.
;
_journal_issue                   16
_journal_name_full               'The Journal of organic chemistry'
_journal_page_first              8217
_journal_page_last               8224
_journal_paper_doi               10.1021/acs.joc.5b01280
_journal_volume                  80
_journal_year                    2015
_chemical_formula_sum            'C22 H19 N3 S'
_chemical_formula_weight         357.46
_chemical_name_systematic
; 
 ? 
;
_space_group_IT_number           15
_symmetry_cell_setting           monoclinic
_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     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 109.51(3)
_cell_angle_gamma                90.00
_cell_formula_units_Z            8
_cell_length_a                   17.079(4)
_cell_length_b                   9.870(2)
_cell_length_c                   23.448(6)
_cell_measurement_reflns_used    721
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      19.4580
_cell_measurement_theta_min      3.9460
_cell_volume                     3725.7(16)
_computing_cell_refinement       'Bruker FRAMBO'
_computing_data_collection       'Bruker FRAMBO'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_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  0.1316
_diffrn_reflns_av_sigmaI/netI    0.1941
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_h_min       -20
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       27
_diffrn_reflns_limit_l_min       -27
_diffrn_reflns_number            8842
_diffrn_reflns_theta_full        25.02
_diffrn_reflns_theta_max         25.02
_diffrn_reflns_theta_min         2.74
_exptl_absorpt_coefficient_mu    0.184
_exptl_absorpt_correction_T_max  0.9958
_exptl_absorpt_correction_T_min  0.9268
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   sadabs
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.275
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             1504
_exptl_crystal_size_max          0.42
_exptl_crystal_size_mid          0.21
_exptl_crystal_size_min          0.02
_refine_diff_density_max         0.257
_refine_diff_density_min         -0.287
_refine_diff_density_rms         0.059
_refine_ls_extinction_coef       0.00113(11)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_ref   0.970
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     236
_refine_ls_number_reflns         3280
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.970
_refine_ls_R_factor_all          0.2014
_refine_ls_R_factor_gt           0.0747
_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/[σ²(Fo²)+(0.0002P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0906
_refine_ls_wR_factor_ref         0.1334
_reflns_number_gt                1307
_reflns_number_total             3280
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jo5b01280_si_002.cif
_cod_data_source_block           141130f
_cod_depositor_comments
;
The following automatic conversions were performed:

'_symmetry_cell_setting' value 'Monoclinic' changed to 'monoclinic'
according to
/usr/data/users/saulius/crontab/automatic-downloads/rss-feeds/ACS/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 3271 2015-04-21 07:52:19Z andrius 

 Adding full bibliography for 4031335.cif.
;
_cod_original_cell_volume        3725.8(15)
_cod_original_sg_symbol_H-M      C2/c
_cod_database_code               4031335
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y, -z+1/2'
'x+1/2, y+1/2, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y, z-1/2'
'-x+1/2, -y+1/2, -z'
'x+1/2, -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
N1 N 0.2966(3) 0.3083(4) 0.15712(17) 0.0450(12) Uani 1 1 d .
N2 N 0.2164(3) 0.2619(4) 0.13285(17) 0.0412(11) Uani 1 1 d .
N3 N 0.3836(3) 0.4343(5) 0.24061(18) 0.0691(16) Uani 1 1 d .
H3A H 0.3903 0.4756 0.2742 0.083 Uiso 1 1 calc R
H3B H 0.4240 0.4295 0.2266 0.083 Uiso 1 1 calc R
S1 S 0.22307(9) 0.45644(14) 0.28263(6) 0.0507(5) Uani 1 1 d .
C1 C 0.3088(4) 0.3766(5) 0.2095(2) 0.0464(15) Uani 1 1 d .
C2 C 0.2369(3) 0.3706(5) 0.2220(2) 0.0401(13) Uani 1 1 d .
C3 C 0.1809(3) 0.2997(5) 0.1730(2) 0.0411(14) Uani 1 1 d .
C4 C 0.0945(4) 0.2622(5) 0.1616(2) 0.0415(14) Uani 1 1 d .
C5 C 0.0418(4) 0.3416(7) 0.1798(3) 0.076(2) Uani 1 1 d .
H5 H 0.0619 0.4212 0.2008 0.091 Uiso 1 1 calc R
C6 C -0.0415(4) 0.3069(9) 0.1678(3) 0.098(3) Uani 1 1 d .
H6 H -0.0766 0.3626 0.1803 0.118 Uiso 1 1 calc R
C7 C -0.0699(4) 0.1893(8) 0.1374(3) 0.080(2) Uani 1 1 d .
H7 H -0.1250 0.1643 0.1298 0.096 Uiso 1 1 calc R
C8 C -0.0205(4) 0.1088(7) 0.1181(3) 0.073(2) Uani 1 1 d .
H8 H -0.0410 0.0291 0.0973 0.088 Uiso 1 1 calc R
C9 C 0.0616(4) 0.1461(6) 0.1296(2) 0.0593(17) Uani 1 1 d .
H9 H 0.0955 0.0916 0.1153 0.071 Uiso 1 1 calc R
C10 C 0.3520(3) 0.2884(5) 0.1236(2) 0.0462(14) Uani 1 1 d .
C11 C 0.4300(4) 0.2405(6) 0.1519(3) 0.076(2) Uani 1 1 d .
H11 H 0.4473 0.2196 0.1929 0.091 Uiso 1 1 calc R
C12 C 0.4828(4) 0.2232(7) 0.1197(3) 0.093(2) Uani 1 1 d .
H12 H 0.5365 0.1916 0.1390 0.112 Uiso 1 1 calc R
C13 C 0.4572(4) 0.2522(7) 0.0590(3) 0.083(2) Uani 1 1 d .
H13 H 0.4933 0.2395 0.0373 0.100 Uiso 1 1 calc R
C14 C 0.3790(4) 0.2994(6) 0.0306(3) 0.0686(19) Uani 1 1 d .
H14 H 0.3615 0.3180 -0.0106 0.082 Uiso 1 1 calc R
C15 C 0.3257(3) 0.3197(5) 0.0629(2) 0.0541(16) Uani 1 1 d .
H15 H 0.2726 0.3541 0.0439 0.065 Uiso 1 1 calc R
C16 C 0.2643(3) 0.3438(5) 0.3446(2) 0.0378(13) Uani 1 1 d .
C17 C 0.2799(3) 0.3992(5) 0.4011(2) 0.0526(16) Uani 1 1 d .
H17 H 0.2682 0.4898 0.4055 0.063 Uiso 1 1 calc R
C18 C 0.3138(3) 0.3163(6) 0.4516(2) 0.0565(17) Uani 1 1 d .
H18 H 0.3249 0.3533 0.4900 0.068 Uiso 1 1 calc R
C19 C 0.3315(3) 0.1809(6) 0.4465(2) 0.0489(15) Uani 1 1 d .
C20 C 0.3135(3) 0.1307(6) 0.3890(2) 0.0531(16) Uani 1 1 d .
H20 H 0.3234 0.0396 0.3839 0.064 Uiso 1 1 calc R
C21 C 0.2815(3) 0.2103(5) 0.3390(2) 0.0504(15) Uani 1 1 d .
H21 H 0.2713 0.1733 0.3007 0.061 Uiso 1 1 calc R
C22 C 0.3714(4) 0.0931(6) 0.5016(2) 0.0717(19) Uani 1 1 d .
H22A H 0.3306 0.0689 0.5197 0.108 Uiso 1 1 calc R
H22B H 0.4157 0.1423 0.5303 0.108 Uiso 1 1 calc R
H22C H 0.3932 0.0124 0.4896 0.108 Uiso 1 1 calc R
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'
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
C1 N1 N2 111.8(4)
C1 N1 C10 129.6(5)
N2 N1 C10 118.5(4)
C3 N2 N1 103.9(4)
C2 S1 C16 103.8(2)
C2 C1 N1 107.3(5)
C2 C1 N3 131.1(5)
N1 C1 N3 121.6(5)
C1 C2 C3 105.3(4)
C1 C2 S1 122.4(4)
C3 C2 S1 131.9(4)
N2 C3 C2 111.7(5)
N2 C3 C4 118.1(5)
C2 C3 C4 130.2(5)
C5 C4 C9 117.1(6)
C5 C4 C3 122.0(5)
C9 C4 C3 120.8(5)
C4 C5 C6 122.0(6)
C7 C6 C5 118.3(7)
C8 C7 C6 121.7(7)
C7 C8 C9 119.1(6)
C4 C9 C8 121.7(6)
C11 C10 C15 120.8(6)
C11 C10 N1 119.9(5)
C15 C10 N1 119.3(5)
C10 C11 C12 119.5(6)
C11 C12 C13 120.4(7)
C14 C13 C12 120.0(7)
C13 C14 C15 120.1(6)
C10 C15 C14 119.1(5)
C21 C16 C17 119.9(5)
C21 C16 S1 124.3(4)
C17 C16 S1 115.8(4)
C16 C17 C18 118.5(5)
C19 C18 C17 122.2(5)
C20 C19 C18 116.7(5)
C20 C19 C22 121.4(5)
C18 C19 C22 121.8(5)
C21 C20 C19 122.1(5)
C16 C21 C20 120.6(5)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
N1 C1 1.356(6)
N1 N2 1.374(5)
N1 C10 1.431(6)
N2 C3 1.333(6)
N3 C1 1.366(6)
S1 C2 1.738(5)
S1 C16 1.778(5)
C1 C2 1.356(7)
C2 C3 1.410(6)
C3 C4 1.457(7)
C4 C5 1.364(7)
C4 C9 1.382(6)
C5 C6 1.397(8)
C6 C7 1.364(8)
C7 C8 1.343(8)
C8 C9 1.386(7)
C10 C11 1.359(7)
C10 C15 1.377(6)
C11 C12 1.368(8)
C12 C13 1.372(8)
C13 C14 1.359(8)
C14 C15 1.380(7)
C16 C21 1.365(6)
C16 C17 1.373(6)
C17 C18 1.397(6)
C18 C19 1.384(6)
C19 C20 1.371(6)
C19 C22 1.515(6)
C20 C21 1.366(6)
