#------------------------------------------------------------------------------
#$Date: 2022-10-26 04:29:19 +0300 (Wed, 26 Oct 2022) $
#$Revision: 278792 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/24/57/7245718.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_7245718
loop_
_publ_author_name
'Feng, Guipeng'
'Meng, Jie'
'Xu, Shaohong'
'Gao, Yao'
'Zhu, Yingying'
'Huang, Ziyu'
_publ_section_title
;
 Copper-catalyzed cross coupling reaction of sulfonyl hydrazides with
 3-aminoindazoles
;
_journal_issue                   47
_journal_name_full               'RSC Advances'
_journal_page_first              30432
_journal_page_last               30435
_journal_paper_doi               10.1039/D2RA05956H
_journal_volume                  12
_journal_year                    2022
_chemical_formula_sum            'C14 H13 N3 O2 S'
_chemical_formula_weight         287.33
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2yn'
_space_group_name_H-M_alt        'P 1 21/n 1'
_atom_sites_solution_hydrogens   mixed
_audit_creation_method           SHELXL-2014/7
_audit_update_record
;
2022-08-28 deposited with the CCDC.	2022-10-19 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 104.633(2)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   8.3551(8)
_cell_length_b                   11.7955(11)
_cell_length_c                   14.7480(13)
_cell_measurement_reflns_used    2983
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      26.70
_cell_measurement_theta_min      2.24
_cell_volume                     1406.3(2)
_computing_cell_refinement       'Bruker SMART'
_computing_data_collection       'Bruker SMART'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_structure_solution    'Bruker SHELXTL'
_diffrn_ambient_temperature      296(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_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0203
_diffrn_reflns_av_unetI/netI     0.0220
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       8
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            7002
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_theta_full        24.996
_diffrn_reflns_theta_max         24.996
_diffrn_reflns_theta_min         3.055
_exptl_absorpt_coefficient_mu    0.235
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            COLORLESS
_exptl_crystal_density_diffrn    1.357
_exptl_crystal_description       BLOCK
_exptl_crystal_F_000             600
_exptl_crystal_size_max          0.260
_exptl_crystal_size_mid          0.250
_exptl_crystal_size_min          0.240
_refine_diff_density_max         0.250
_refine_diff_density_min         -0.488
_refine_diff_density_rms         0.044
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.989
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     190
_refine_ls_number_reflns         2466
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.989
_refine_ls_R_factor_all          0.0498
_refine_ls_R_factor_gt           0.0405
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0691P)²+0.4080P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1073
_refine_ls_wR_factor_ref         0.1137
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2034
_reflns_number_total             2466
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d2ra05956h2.cif
_cod_data_source_block           1
_cod_original_sg_symbol_H-M      'P 21/n'
_cod_database_code               7245718
_shelx_shelxl_version_number     2014/7
_shelx_space_group_comment
; 
The symmetry employed for this shelxl refinement is uniquely defined 
by the following loop, which should always be used as a source of 
symmetry information in preference to the above space-group names. 
They are only intended as comments. 
;
_shelx_estimated_absorpt_t_min   0.942
_shelx_estimated_absorpt_t_max   0.946
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -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_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
S1 S 0.09772(6) 0.18082(4) 0.38374(4) 0.0472(2) Uani 1 1 d . . . . .
O2 O -0.03410(18) 0.21067(15) 0.30547(12) 0.0688(5) Uani 1 1 d . . . . .
N3 N 0.2445(2) 0.13162(14) 0.33652(11) 0.0427(4) Uani 1 1 d . . . . .
O1 O 0.0737(2) 0.09693(13) 0.44839(12) 0.0687(5) Uani 1 1 d . . . . .
N2 N 0.3754(2) 0.07289(13) 0.39887(11) 0.0449(4) Uani 1 1 d . . . . .
C13 C 0.4694(2) 0.15923(15) 0.28294(13) 0.0380(4) Uani 1 1 d . . . . .
N1 N 0.6486(3) 0.0310(2) 0.40255(19) 0.0641(6) Uani 1 1 d . . . . .
C8 C 0.3051(2) 0.19142(15) 0.26988(12) 0.0387(4) Uani 1 1 d . . . . .
C5 C 0.1759(2) 0.30472(15) 0.44359(13) 0.0390(4) Uani 1 1 d . . . . .
C14 C 0.5044(2) 0.08574(16) 0.36451(13) 0.0409(4) Uani 1 1 d . . . . .
C12 C 0.5641(3) 0.20212(18) 0.22584(14) 0.0496(5) Uani 1 1 d . . . . .
H12 H 0.6729 0.1789 0.2329 0.060 Uiso 1 1 calc R U . . .
C9 C 0.2313(3) 0.26938(18) 0.20193(14) 0.0502(5) Uani 1 1 d . . . . .
H9 H 0.1214 0.2910 0.1935 0.060 Uiso 1 1 calc R U . . .
C4 C 0.2894(3) 0.29734(17) 0.52980(14) 0.0495(5) Uani 1 1 d . . . . .
H4 H 0.3235 0.2269 0.5561 0.059 Uiso 1 1 calc R U . . .
C2 C 0.3025(3) 0.50078(18) 0.53862(15) 0.0542(5) Uani 1 1 d . . . . .
C10 C 0.3281(3) 0.31349(19) 0.14746(15) 0.0587(6) Uani 1 1 d . . . . .
H10 H 0.2830 0.3672 0.1020 0.070 Uiso 1 1 calc R U . . .
C3 C 0.3510(3) 0.39515(19) 0.57614(15) 0.0551(6) Uani 1 1 d . . . . .
H3 H 0.4272 0.3902 0.6341 0.066 Uiso 1 1 calc R U . . .
C6 C 0.1270(3) 0.40912(19) 0.40457(15) 0.0586(6) Uani 1 1 d . . . . .
H6 H 0.0512 0.4141 0.3465 0.070 Uiso 1 1 calc R U . . .
C11 C 0.4919(3) 0.2799(2) 0.15863(15) 0.0584(6) Uani 1 1 d . . . . .
H11 H 0.5532 0.3105 0.1200 0.070 Uiso 1 1 calc R U . . .
C7 C 0.1910(3) 0.50593(19) 0.45206(17) 0.0671(7) Uani 1 1 d . . . . .
H7 H 0.1585 0.5763 0.4252 0.080 Uiso 1 1 calc R U . . .
C1 C 0.3693(4) 0.6076(2) 0.5913(2) 0.0853(9) Uani 1 1 d . . . . .
H1C H 0.3234 0.6160 0.6444 0.128 Uiso 1 1 calc R U . . .
H1D H 0.3394 0.6719 0.5507 0.128 Uiso 1 1 calc R U . . .
H1E H 0.4876 0.6028 0.6124 0.128 Uiso 1 1 calc R U . . .
H1A H 0.718(4) 0.054(3) 0.384(2) 0.077(10) Uiso 1 1 d . . . . .
H1B H 0.669(4) 0.003(3) 0.457(2) 0.091(10) 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 0.0000 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
O1 S1 O2 120.27(11) . . ?
O1 S1 N3 106.37(9) . . ?
O2 S1 N3 104.39(9) . . ?
O1 S1 C5 109.95(9) . . ?
O2 S1 C5 108.47(10) . . ?
N3 S1 C5 106.45(8) . . ?
C8 N3 N2 110.09(15) . . ?
C8 N3 S1 123.59(13) . . ?
N2 N3 S1 115.40(12) . . ?
C14 N2 N3 105.51(15) . . ?
C12 C13 C8 120.69(18) . . ?
C12 C13 C14 133.97(18) . . ?
C8 C13 C14 105.25(16) . . ?
C14 N1 H1A 112(2) . . ?
C14 N1 H1B 122(2) . . ?
H1A N1 H1B 119(3) . . ?
C9 C8 C13 121.71(18) . . ?
C9 C8 N3 131.79(19) . . ?
C13 C8 N3 106.50(16) . . ?
C6 C5 C4 120.16(18) . . ?
C6 C5 S1 120.24(15) . . ?
C4 C5 S1 119.59(15) . . ?
N2 C14 N1 121.1(2) . . ?
N2 C14 C13 112.13(17) . . ?
N1 C14 C13 126.8(2) . . ?
C11 C12 C13 117.9(2) . . ?
C11 C12 H12 121.1 . . ?
C13 C12 H12 121.1 . . ?
C10 C9 C8 116.9(2) . . ?
C10 C9 H9 121.5 . . ?
C8 C9 H9 121.5 . . ?
C3 C4 C5 119.23(19) . . ?
C3 C4 H4 120.4 . . ?
C5 C4 H4 120.4 . . ?
C7 C2 C3 118.16(19) . . ?
C7 C2 C1 121.0(2) . . ?
C3 C2 C1 120.8(2) . . ?
C9 C10 C11 121.8(2) . . ?
C9 C10 H10 119.1 . . ?
C11 C10 H10 119.1 . . ?
C4 C3 C2 121.5(2) . . ?
C4 C3 H3 119.2 . . ?
C2 C3 H3 119.2 . . ?
C7 C6 C5 119.6(2) . . ?
C7 C6 H6 120.2 . . ?
C5 C6 H6 120.2 . . ?
C12 C11 C10 121.0(2) . . ?
C12 C11 H11 119.5 . . ?
C10 C11 H11 119.5 . . ?
C6 C7 C2 121.3(2) . . ?
C6 C7 H7 119.3 . . ?
C2 C7 H7 119.3 . . ?
C2 C1 H1C 109.5 . . ?
C2 C1 H1D 109.5 . . ?
H1C C1 H1D 109.5 . . ?
C2 C1 H1E 109.5 . . ?
H1C C1 H1E 109.5 . . ?
H1D C1 H1E 109.5 . . ?
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 O1 1.4230(16) . ?
S1 O2 1.4237(17) . ?
S1 N3 1.6605(16) . ?
S1 C5 1.7464(18) . ?
N3 C8 1.404(2) . ?
N3 N2 1.419(2) . ?
N2 C14 1.310(2) . ?
C13 C12 1.388(3) . ?
C13 C8 1.390(3) . ?
C13 C14 1.451(3) . ?
N1 C14 1.357(3) . ?
N1 H1A 0.75(3) . ?
N1 H1B 0.84(3) . ?
C8 C9 1.385(3) . ?
C5 C6 1.377(3) . ?
C5 C4 1.384(3) . ?
C12 C11 1.373(3) . ?
C12 H12 0.9300 . ?
C9 C10 1.378(3) . ?
C9 H9 0.9300 . ?
C4 C3 1.373(3) . ?
C4 H4 0.9300 . ?
C2 C7 1.378(3) . ?
C2 C3 1.382(3) . ?
C2 C1 1.511(3) . ?
C10 C11 1.394(3) . ?
C10 H10 0.9300 . ?
C3 H3 0.9300 . ?
C6 C7 1.375(3) . ?
C6 H6 0.9300 . ?
C11 H11 0.9300 . ?
C7 H7 0.9300 . ?
C1 H1C 0.9600 . ?
C1 H1D 0.9600 . ?
C1 H1E 0.9600 . ?
loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
O1 S1 N3 C8 -178.98(15) . . . . ?
O2 S1 N3 C8 52.87(17) . . . . ?
C5 S1 N3 C8 -61.75(16) . . . . ?
O1 S1 N3 N2 -38.47(15) . . . . ?
O2 S1 N3 N2 -166.62(13) . . . . ?
C5 S1 N3 N2 78.75(14) . . . . ?
C8 N3 N2 C14 -7.1(2) . . . . ?
S1 N3 N2 C14 -152.73(13) . . . . ?
C12 C13 C8 C9 -2.0(3) . . . . ?
C14 C13 C8 C9 175.00(17) . . . . ?
C12 C13 C8 N3 178.56(16) . . . . ?
C14 C13 C8 N3 -4.48(19) . . . . ?
N2 N3 C8 C9 -172.17(19) . . . . ?
S1 N3 C8 C9 -29.9(3) . . . . ?
N2 N3 C8 C13 7.24(19) . . . . ?
S1 N3 C8 C13 149.52(14) . . . . ?
O1 S1 C5 C6 -143.54(18) . . . . ?
O2 S1 C5 C6 -10.2(2) . . . . ?
N3 S1 C5 C6 101.63(18) . . . . ?
O1 S1 C5 C4 37.56(19) . . . . ?
O2 S1 C5 C4 170.91(16) . . . . ?
N3 S1 C5 C4 -77.26(17) . . . . ?
N3 N2 C14 N1 -173.84(19) . . . . ?
N3 N2 C14 C13 4.2(2) . . . . ?
C12 C13 C14 N2 176.5(2) . . . . ?
C8 C13 C14 N2 0.2(2) . . . . ?
C12 C13 C14 N1 -5.6(4) . . . . ?
C8 C13 C14 N1 178.0(2) . . . . ?
C8 C13 C12 C11 2.2(3) . . . . ?
C14 C13 C12 C11 -173.7(2) . . . . ?
C13 C8 C9 C10 0.2(3) . . . . ?
N3 C8 C9 C10 179.53(19) . . . . ?
C6 C5 C4 C3 0.7(3) . . . . ?
S1 C5 C4 C3 179.58(17) . . . . ?
C8 C9 C10 C11 1.3(3) . . . . ?
C5 C4 C3 C2 -0.1(3) . . . . ?
C7 C2 C3 C4 -0.8(4) . . . . ?
C1 C2 C3 C4 178.9(2) . . . . ?
C4 C5 C6 C7 -0.4(3) . . . . ?
S1 C5 C6 C7 -179.26(19) . . . . ?
C13 C12 C11 C10 -0.8(3) . . . . ?
C9 C10 C11 C12 -1.0(3) . . . . ?
C5 C6 C7 C2 -0.6(4) . . . . ?
C3 C2 C7 C6 1.2(4) . . . . ?
C1 C2 C7 C6 -178.6(3) . . . . ?
