#------------------------------------------------------------------------------
#$Date: 2021-10-05 12:59:44 +0300 (Tue, 05 Oct 2021) $
#$Revision: 269560 $
#$URL: file:///home/coder/svn-repositories/cod/cif/4/03/89/4038953.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_4038953
loop_
_publ_author_name
'Vasin, V.A.'
'Masterova, Yu.Yu.'
'Bezrukova, E.V.'
'Razin, V.V.'
'Somov, N.V.'
_publ_section_title
;
 Synthesis of 3H-Pyrazoles by Reaction of Methyl and p-Tolyl Phenylethynyl
 Sulfones with Diphenyldiazomethane and Their Thermal and Acid-Catalyzed
 Transformations
;
_journal_issue                   6
_journal_name_full
;
 Russian Journal of Organic Chemistry
;
_journal_page_first              874
_journal_page_last               883
_journal_paper_doi               10.1134/S107042801506010X
_journal_volume                  51
_journal_year                    2015
_chemical_formula_sum            'C22 H18 N2 O2 S'
_chemical_formula_weight         374.44
_chemical_name_systematic
;
 ?14:50 23.03.2015
;
_space_group_IT_number           14
_space_group_name_Hall           '-P 2ybc'
_space_group_name_H-M_alt        'P 1 21/c 1'
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_H-M   'P 1 21/c 1'
_atom_sites_solution_hydrogens   difmap
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_conform_dict_location     ftp://ftp.iucr.org/pub/cif_core.dic
_audit_conform_dict_name         cif_core.dic
_audit_conform_dict_version      2.4
_audit_creation_date             2012-09-26
_audit_creation_method           'WinGX routine CIF_UPDATE'
_audit_update_record             ?
_cell_angle_alpha                90
_cell_angle_beta                 96.044(3)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   9.8194(4)
_cell_length_b                   20.4689(7)
_cell_length_c                   9.6034(3)
_cell_measurement_reflns_used    12102
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      32.9919
_cell_measurement_theta_min      3.447
_cell_volume                     1919.48(12)
_computing_cell_refinement
;
        CrysAlisPro, Agilent Technologies,
        Version 1.171.35.21 (release 20-01-2012 CrysAlis171 .NET)
        (compiled Jan 23 2012,18:06:46)
;
_computing_data_collection
;
        CrysAlisPro, Agilent Technologies,
        Version 1.171.35.21 (release 20-01-2012 CrysAlis171 .NET)
        (compiled Jan 23 2012,18:06:46)
;
_computing_data_reduction
;
        CrysAlisPro, Agilent Technologies,
        Version 1.171.35.21 (release 20-01-2012 CrysAlis171 .NET)
        (compiled Jan 23 2012,18:06:46)
;
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      293(2)
_diffrn_detector_area_resol_mean 16.0302
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measurement_device_type  'Xcalibur, Sapphire3, Gemini'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_UB_11      0.0305479
_diffrn_orient_matrix_UB_12      -0.0239958
_diffrn_orient_matrix_UB_13      0.0466045
_diffrn_orient_matrix_UB_21      0.0345554
_diffrn_orient_matrix_UB_22      0.0248934
_diffrn_orient_matrix_UB_23      0.0411809
_diffrn_orient_matrix_UB_31      -0.0560933
_diffrn_orient_matrix_UB_32      0.0022992
_diffrn_orient_matrix_UB_33      0.0406355
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0242
_diffrn_reflns_av_unetI/netI     0.0162
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       29
_diffrn_reflns_limit_k_min       -29
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            37041
_diffrn_reflns_theta_full        30.5
_diffrn_reflns_theta_max         30.5
_diffrn_reflns_theta_min         3.45
_exptl_absorpt_coefficient_mu    0.188
_exptl_absorpt_correction_T_max  1
_exptl_absorpt_correction_T_min  0.95007
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
        CrysAlisPro, Agilent Technologies,
        Version 1.171.35.21 (release 20-01-2012 CrysAlis171 .NET)
        (compiled Jan 23 2012,18:06:46)
        Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_density_diffrn    1.296
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             784
_exptl_crystal_size_max          0.3084
_exptl_crystal_size_mid          0.2638
_exptl_crystal_size_min          0.1599
_refine_diff_density_max         0.412
_refine_diff_density_min         -0.177
_refine_diff_density_rms         0.052
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.12
_refine_ls_hydrogen_treatment    refall
_refine_ls_matrix_type           full
_refine_ls_number_parameters     316
_refine_ls_number_reflns         5841
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.12
_refine_ls_R_factor_all          0.0665
_refine_ls_R_factor_gt           0.057
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0742P)²+0.3640P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1404
_refine_ls_wR_factor_ref         0.1473
_reflns_number_gt                5010
_reflns_number_total             5841
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            tmpmrs5qe6k
_cod_data_source_block           global
_cod_database_code               4038953
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
C1 C 0.65585(18) 0.71594(12) 0.6767(2) 0.0608(5) Uani 1 1 d . . .
C2 C 0.7636(2) 0.75105(16) 0.6300(3) 0.0821(8) Uani 1 1 d . . .
C3 C 0.7432(3) 0.81196(18) 0.5755(3) 0.0922(9) Uani 1 1 d . . .
C4 C 0.6163(3) 0.84036(16) 0.5675(3) 0.0907(9) Uani 1 1 d . . .
C5 C 0.5069(2) 0.80691(11) 0.6125(2) 0.0617(5) Uani 1 1 d . . .
C6 C 0.52609(16) 0.74371(8) 0.66511(16) 0.0431(3) Uani 1 1 d . . .
C7 C 0.40604(14) 0.70928(7) 0.70755(15) 0.0364(3) Uani 1 1 d . . .
C8 C 0.35901(13) 0.64779(6) 0.69560(14) 0.0328(3) Uani 1 1 d . . .
C9 C 0.22089(13) 0.64525(6) 0.75187(14) 0.0336(3) Uani 1 1 d . . .
C10 C 0.09061(17) 0.67270(9) 0.52007(18) 0.0500(4) Uani 1 1 d . . .
C11 C 0.10416(14) 0.63212(7) 0.63619(15) 0.0363(3) Uani 1 1 d . . .
C12 C 0.0115(2) 0.58213(10) 0.6444(2) 0.0581(5) Uani 1 1 d . . .
C13 C -0.0932(2) 0.57282(13) 0.5380(2) 0.0734(6) Uani 1 1 d . . .
C14 C -0.1064(2) 0.61286(13) 0.4236(2) 0.0675(5) Uani 1 1 d . . .
C15 C -0.0141(2) 0.66271(12) 0.4143(2) 0.0646(5) Uani 1 1 d . . .
C16 C 0.21390(15) 0.60559(7) 0.88573(15) 0.0392(3) Uani 1 1 d . . .
C17 C 0.1104(2) 0.61851(14) 0.9684(2) 0.0727(6) Uani 1 1 d . . .
C18 C 0.1037(3) 0.58437(17) 1.0928(3) 0.0925(10) Uani 1 1 d . . .
C19 C 0.3099(2) 0.55899(10) 0.93049(19) 0.0559(4) Uani 1 1 d . . .
C20 C 0.3017(3) 0.52611(12) 1.0558(2) 0.0700(6) Uani 1 1 d . . .
C21 C 0.1997(3) 0.53903(14) 1.1363(2) 0.0761(7) Uani 1 1 d . . .
C22 C 0.4562(3) 0.61164(11) 0.44260(18) 0.0572(5) Uani 1 1 d . . .
O1 O 0.56160(13) 0.56677(7) 0.68342(14) 0.0566(3) Uani 1 1 d . . .
O2 O 0.33215(14) 0.53091(6) 0.59519(16) 0.0636(4) Uani 1 1 d . . .
S1 S 0.43130(4) 0.581707(16) 0.60962(4) 0.03895(12) Uani 1 1 d . . .
N1 N 0.20586(13) 0.71512(6) 0.79714(14) 0.0428(3) Uani 1 1 d . . .
N2 N 0.30652(14) 0.74883(6) 0.77215(15) 0.0450(3) Uani 1 1 d . . .
H1 H 0.039(3) 0.6478(14) 0.939(3) 0.087(8) Uiso 1 1 d . . .
H2 H 0.045(4) 0.5980(19) 1.136(4) 0.122(12) Uiso 1 1 d . . .
H3 H 0.191(2) 0.5178(14) 1.217(3) 0.080(7) Uiso 1 1 d . . .
H4 H 0.368(3) 0.4981(16) 1.091(3) 0.092(8) Uiso 1 1 d . . .
H5 H 0.387(3) 0.5483(13) 0.870(3) 0.087(8) Uiso 1 1 d . . .
H6 H 0.371(3) 0.6265(13) 0.402(3) 0.081(8) Uiso 1 1 d . . .
H7 H 0.493(2) 0.5748(13) 0.397(3) 0.073(7) Uiso 1 1 d . . .
H8 H 0.512(3) 0.6487(19) 0.450(3) 0.115(11) Uiso 1 1 d . . .
H9 H -0.024(2) 0.6934(13) 0.336(3) 0.075(7) Uiso 1 1 d . . .
H10 H -0.178(3) 0.6115(16) 0.346(3) 0.103(9) Uiso 1 1 d . . .
H11 H -0.150(2) 0.5376(13) 0.540(3) 0.076(7) Uiso 1 1 d . . .
H12 H 0.021(2) 0.5528(13) 0.723(3) 0.077(7) Uiso 1 1 d . . .
H13 H 0.415(3) 0.8290(13) 0.609(3) 0.077(7) Uiso 1 1 d . . .
H14 H 0.820(4) 0.8368(19) 0.536(4) 0.126(11) Uiso 1 1 d . . .
H15 H 0.857(3) 0.7308(14) 0.646(3) 0.094(8) Uiso 1 1 d . . .
H16 H 0.667(2) 0.6728(14) 0.715(3) 0.071(7) Uiso 1 1 d . . .
H17 H 0.155(2) 0.7053(12) 0.511(2) 0.066(6) Uiso 1 1 d . . .
H18 H 0.596(3) 0.8827(16) 0.533(3) 0.098(9) Uiso 1 1 d . . .
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 0 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.006 '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'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
-1 -29 0 0.1111
0 -13 12 0.1034
13 -12 -1 0.0731
-13 10 0 0.0774
0 19 10 0.1103
0 29 0 0.1378
13 10 0 0.0958
0 18 -11 0.1488
1 -12 -12 0.1552
-12 -12 0 0.0866
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
C6 C1 C2 119.0(2) . . ?
C6 C1 H16 118.4(14) . . ?
C2 C1 H16 122.5(14) . . ?
C3 C2 C1 120.8(3) . . ?
C3 C2 H15 122.2(17) . . ?
C1 C2 H15 116.8(17) . . ?
C2 C3 C4 120.5(2) . . ?
C2 C3 H14 121(2) . . ?
C4 C3 H14 118(2) . . ?
C3 C4 C5 120.3(3) . . ?
C3 C4 H18 124.6(19) . . ?
C5 C4 H18 115.1(19) . . ?
C4 C5 C6 119.6(2) . . ?
C4 C5 H13 119.4(15) . . ?
C6 C5 H13 121.1(15) . . ?
C1 C6 C5 119.78(17) . . ?
C1 C6 C7 122.56(16) . . ?
C5 C6 C7 117.66(15) . . ?
C8 C7 N2 108.52(12) . . ?
C8 C7 C6 134.93(13) . . ?
N2 C7 C6 116.47(12) . . ?
C7 C8 C9 108.37(11) . . ?
C7 C8 S1 127.23(10) . . ?
C9 C8 S1 123.96(10) . . ?
N1 C9 C8 100.91(10) . . ?
N1 C9 C16 104.31(11) . . ?
C8 C9 C16 116.11(11) . . ?
N1 C9 C11 106.68(11) . . ?
C8 C9 C11 112.15(11) . . ?
C16 C9 C11 114.83(11) . . ?
C15 C10 C11 120.23(17) . . ?
C15 C10 H17 119.7(14) . . ?
C11 C10 H17 120.0(15) . . ?
C12 C11 C10 118.92(15) . . ?
C12 C11 C9 122.46(13) . . ?
C10 C11 C9 118.62(13) . . ?
C11 C12 C13 120.27(18) . . ?
C11 C12 H12 119.7(15) . . ?
C13 C12 H12 120.0(15) . . ?
C14 C13 C12 120.74(19) . . ?
C14 C13 H11 119.1(16) . . ?
C12 C13 H11 120.0(16) . . ?
C13 C14 C15 119.35(18) . . ?
C13 C14 H10 126.9(19) . . ?
C15 C14 H10 113.7(19) . . ?
C14 C15 C10 120.48(19) . . ?
C14 C15 H9 120.8(14) . . ?
C10 C15 H9 118.6(15) . . ?
C19 C16 C17 118.32(16) . . ?
C19 C16 C9 122.72(13) . . ?
C17 C16 C9 118.91(15) . . ?
C16 C17 C18 120.1(2) . . ?
C16 C17 H1 121.4(17) . . ?
C18 C17 H1 118.3(17) . . ?
C21 C18 C17 120.9(2) . . ?
C21 C18 H2 127(3) . . ?
C17 C18 H2 112(3) . . ?
C16 C19 C20 120.41(18) . . ?
C16 C19 H5 119.6(15) . . ?
C20 C19 H5 120.0(15) . . ?
C21 C20 C19 120.9(2) . . ?
C21 C20 H4 117.5(18) . . ?
C19 C20 H4 121.4(18) . . ?
C20 C21 C18 119.29(19) . . ?
C20 C21 H3 122.8(16) . . ?
C18 C21 H3 117.9(16) . . ?
S1 C22 H6 106.6(17) . . ?
S1 C22 H7 103.7(15) . . ?
H6 C22 H7 116(2) . . ?
S1 C22 H8 111(2) . . ?
H6 C22 H8 105(3) . . ?
H7 C22 H8 115(3) . . ?
O2 S1 O1 117.40(9) . . ?
O2 S1 C22 109.01(11) . . ?
O1 S1 C22 108.89(10) . . ?
O2 S1 C8 107.46(7) . . ?
O1 S1 C8 108.30(7) . . ?
C22 S1 C8 105.08(8) . . ?
N2 N1 C9 111.43(11) . . ?
N1 N2 C7 110.76(12) . . ?
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
C1 C6 1.389(3) . ?
C1 C2 1.391(3) . ?
C1 H16 0.96(3) . ?
C2 C3 1.359(5) . ?
C2 H15 1.01(3) . ?
C3 C4 1.370(5) . ?
C3 H14 1.01(4) . ?
C4 C5 1.381(3) . ?
C4 H18 0.94(3) . ?
C5 C6 1.394(3) . ?
C5 H13 1.00(3) . ?
C6 C7 1.468(2) . ?
C7 C8 1.3414(19) . ?
C7 N2 1.4571(18) . ?
C8 C9 1.5128(18) . ?
C8 S1 1.7716(13) . ?
C9 N1 1.5065(17) . ?
C9 C16 1.5280(19) . ?
C9 C11 1.5336(19) . ?
C10 C15 1.382(3) . ?
C10 C11 1.386(2) . ?
C10 H17 0.93(2) . ?
C11 C12 1.377(2) . ?
C12 C13 1.385(3) . ?
C12 H12 0.96(3) . ?
C13 C14 1.366(3) . ?
C13 H11 0.91(3) . ?
C14 C15 1.374(3) . ?
C14 H10 0.97(3) . ?
C15 H9 0.98(3) . ?
C16 C19 1.378(2) . ?
C16 C17 1.380(2) . ?
C17 C18 1.391(3) . ?
C17 H1 0.94(3) . ?
C18 C21 1.357(4) . ?
C18 H2 0.80(4) . ?
C19 C20 1.388(3) . ?
C19 H5 1.03(3) . ?
C20 C21 1.355(3) . ?
C20 H4 0.91(3) . ?
C21 H3 0.90(3) . ?
C22 S1 1.7581(19) . ?
C22 H6 0.94(3) . ?
C22 H7 0.96(3) . ?
C22 H8 0.93(4) . ?
O1 S1 1.4289(12) . ?
O2 S1 1.4213(13) . ?
N1 N2 1.2492(18) . ?
