#------------------------------------------------------------------------------
#$Date: 2023-06-05 07:35:37 +0300 (Mon, 05 Jun 2023) $
#$Revision: 284278 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/24/67/7246708.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_7246708
loop_
_publ_author_name
'Zhong, Qiang'
'Wang, Pei-Long'
'Gao, Hui'
'Ma, Fang'
'Yang, Youqing'
'Li, Hongji'
_publ_section_title
;
 Electrochemical intramolecular N(sp2)--H/N(sp3)--H coupling for the
 synthesis of 1H-indazoles
;
_journal_issue                   10
_journal_name_full               'Green Chemistry'
_journal_page_first              3982
_journal_page_last               3988
_journal_paper_doi               10.1039/D3GC00380A
_journal_volume                  25
_journal_year                    2023
_chemical_formula_moiety         'C21 H18 N2 O3 S'
_chemical_formula_sum            'C21 H19 N2 O3 S'
_chemical_formula_weight         379.44
_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   geom
_atom_sites_solution_primary     direct
_audit_creation_date             2022-07-21
_audit_creation_method
;
Olex2 1.3
(compiled 2020.11.12 svn.r5f609507 for OlexSys, GUI svn.r6408)
;
_audit_update_record
;
2022-07-21 deposited with the CCDC.	2023-04-14 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 95.345(5)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   14.2948(8)
_cell_length_b                   8.5708(4)
_cell_length_c                   15.3612(8)
_cell_measurement_reflns_used    5869
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      28.8230
_cell_measurement_theta_min      2.7210
_cell_volume                     1873.84(17)
_computing_molecular_graphics    'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.827
_diffrn_measurement_device_type  'multiwire proportional'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0437
_diffrn_reflns_av_unetI/netI     0.0467
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.827
_diffrn_reflns_limit_h_max       20
_diffrn_reflns_limit_h_min       -17
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_number            17066
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.827
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         30.645
_diffrn_reflns_theta_min         2.724
_exptl_absorpt_coefficient_mu    0.197
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.74346
_exptl_absorpt_correction_type   multi-scan
_exptl_crystal_colour            yellowish
_exptl_crystal_colour_modifier   yellowish
_exptl_crystal_density_diffrn    1.345
_exptl_crystal_description       cubic
_exptl_crystal_F_000             796
_exptl_crystal_recrystallization_method cubic
_exptl_crystal_size_max          0.15
_exptl_crystal_size_mid          0.1
_exptl_crystal_size_min          0.1
_refine_diff_density_max         0.265
_refine_diff_density_min         -0.548
_refine_diff_density_rms         0.048
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.026
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     246
_refine_ls_number_reflns         4789
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.026
_refine_ls_R_factor_all          0.0838
_refine_ls_R_factor_gt           0.0517
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.1010P)²+0.0603P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1545
_refine_ls_wR_factor_ref         0.1746
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3013
_reflns_number_total             4789
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d3gc00380a2.cif
_cod_data_source_block           2
_cod_depositor_comments
'Adding full bibliography for 7246708--7246709.cif.'
_cod_database_code               7246708
_shelx_shelxl_version_number     2018/3
_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_max   0.981
_shelx_estimated_absorpt_t_min   0.971
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C3(H3), C4(H4), C6(H6), C7(H7), C11(H11), C12(H12), C13(H13), C14(H14),
 C16(H16), C17(H17), C19(H19), C20(H20)
2.b Idealised Me refined as rotating group:
 C1(H1A,H1B,H1C), C21(H21A,H21B,H21C)
;
_olex2_submission_special_instructions 'No special instructions were received'
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
C1 C 0.4889(2) 0.5333(3) 0.24762(16) 0.0886(8) Uani 1 1 d . . . . .
H1A H 0.505140 0.460539 0.203969 0.133 Uiso 1 1 calc R U . . .
H1B H 0.482353 0.635707 0.222415 0.133 Uiso 1 1 calc R U . . .
H1C H 0.430680 0.502565 0.268967 0.133 Uiso 1 1 calc R U . . .
C2 C 0.54575(13) 0.6194(2) 0.39095(12) 0.0532(4) Uani 1 1 d . . . . .
C3 C 0.47057(14) 0.7188(2) 0.39752(12) 0.0558(5) Uani 1 1 d . . . . .
H3 H 0.426831 0.735356 0.349709 0.067 Uiso 1 1 calc R U . . .
C4 C 0.46119(13) 0.7936(2) 0.47629(12) 0.0526(4) Uani 1 1 d . . . . .
H4 H 0.410440 0.860064 0.480700 0.063 Uiso 1 1 calc R U . . .
C5 C 0.52514(12) 0.77197(19) 0.54838(11) 0.0449(4) Uani 1 1 d . . . . .
C6 C 0.60176(12) 0.6734(2) 0.53954(12) 0.0525(4) Uani 1 1 d . . . . .
H6 H 0.646686 0.658750 0.586631 0.063 Uiso 1 1 calc R U . . .
C7 C 0.61111(14) 0.5984(2) 0.46226(13) 0.0584(5) Uani 1 1 d . . . . .
H7 H 0.662059 0.532472 0.457560 0.070 Uiso 1 1 calc R U . . .
C8 C 0.51355(12) 0.84822(19) 0.63169(11) 0.0452(4) Uani 1 1 d . . . . .
C9 C 0.42760(12) 0.87443(19) 0.67199(11) 0.0477(4) Uani 1 1 d . . . . .
C10 C 0.45392(14) 0.9495(2) 0.75105(12) 0.0543(4) Uani 1 1 d . . . . .
C11 C 0.33359(14) 0.8348(2) 0.65112(14) 0.0601(5) Uani 1 1 d . . . . .
H11 H 0.314579 0.783625 0.599091 0.072 Uiso 1 1 calc R U . . .
C12 C 0.26983(16) 0.8730(3) 0.70891(17) 0.0747(6) Uani 1 1 d . . . . .
H12 H 0.206891 0.847141 0.695962 0.090 Uiso 1 1 calc R U . . .
C13 C 0.29774(17) 0.9492(3) 0.78602(17) 0.0800(7) Uani 1 1 d . . . . .
H13 H 0.252543 0.974058 0.823567 0.096 Uiso 1 1 calc R U . . .
C14 C 0.38900(18) 0.9898(3) 0.80956(15) 0.0737(6) Uani 1 1 d . . . . .
H14 H 0.406837 1.041477 0.861719 0.088 Uiso 1 1 calc R U . . .
C15 C 0.63949(13) 0.8182(3) 0.89367(12) 0.0597(5) Uani 1 1 d . . . . .
C16 C 0.58759(15) 0.7847(3) 0.96279(13) 0.0619(5) Uani 1 1 d . . . . .
H16 H 0.545141 0.857264 0.980993 0.074 Uiso 1 1 calc R U . . .
C17 C 0.59918(16) 0.6430(3) 1.00450(15) 0.0696(6) Uani 1 1 d . . . . .
H17 H 0.564394 0.621112 1.051250 0.084 Uiso 1 1 calc R U . . .
C18 C 0.66163(16) 0.5319(3) 0.97845(16) 0.0722(6) Uani 1 1 d . . . . .
C19 C 0.71053(16) 0.5671(4) 0.90732(18) 0.0813(7) Uani 1 1 d . . . . .
H19 H 0.751268 0.493160 0.887659 0.098 Uiso 1 1 calc R U . . .
C20 C 0.70069(14) 0.7075(4) 0.86509(15) 0.0777(7) Uani 1 1 d . . . . .
H20 H 0.734669 0.728666 0.817689 0.093 Uiso 1 1 calc R U . . .
C21 C 0.6755(2) 0.3795(3) 1.0268(2) 0.1000(9) Uani 1 1 d . . . . .
H21A H 0.636270 0.377037 1.074232 0.150 Uiso 1 1 calc R U . . .
H21B H 0.740140 0.369653 1.049531 0.150 Uiso 1 1 calc R U . . .
H21C H 0.659042 0.294640 0.987570 0.150 Uiso 1 1 calc R U . . .
N1 N 0.58639(11) 0.90049(19) 0.68126(9) 0.0553(4) Uani 1 1 d . . . . .
N2 N 0.55094(13) 0.9696(2) 0.75382(10) 0.0613(4) Uani 1 1 d . . . . .
O1 O 0.56097(11) 0.53518(19) 0.31796(10) 0.0733(4) Uani 1 1 d . . . . .
O2 O 0.57577(14) 1.10203(18) 0.89497(10) 0.0849(5) Uani 1 1 d . . . . .
O3 O 0.71111(13) 1.0460(3) 0.81066(11) 0.1003(7) Uani 1 1 d . . . . .
S1 S 0.62530(4) 1.00027(7) 0.84173(3) 0.0702(2) Uani 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
H1A C1 H1B 109.5 . . ?
H1A C1 H1C 109.5 . . ?
H1B C1 H1C 109.5 . . ?
O1 C1 H1A 109.5 . . ?
O1 C1 H1B 109.5 . . ?
O1 C1 H1C 109.5 . . ?
C3 C2 C7 119.63(17) . . ?
O1 C2 C3 124.69(18) . . ?
O1 C2 C7 115.67(17) . . ?
C2 C3 H3 120.4 . . ?
C2 C3 C4 119.18(17) . . ?
C4 C3 H3 120.4 . . ?
C3 C4 H4 119.1 . . ?
C5 C4 C3 121.81(16) . . ?
C5 C4 H4 119.1 . . ?
C4 C5 C6 117.94(16) . . ?
C4 C5 C8 121.47(15) . . ?
C6 C5 C8 120.59(15) . . ?
C5 C6 H6 119.7 . . ?
C7 C6 C5 120.56(17) . . ?
C7 C6 H6 119.7 . . ?
C2 C7 H7 119.6 . . ?
C6 C7 C2 120.86(17) . . ?
C6 C7 H7 119.6 . . ?
C9 C8 C5 128.02(15) . . ?
N1 C8 C5 120.90(16) . . ?
N1 C8 C9 111.07(15) . . ?
C10 C9 C8 105.89(15) . . ?
C11 C9 C8 134.75(18) . . ?
C11 C9 C10 119.25(17) . . ?
C14 C10 C9 122.27(18) . . ?
N2 C10 C9 105.69(16) . . ?
N2 C10 C14 132.04(19) . . ?
C9 C11 H11 120.7 . . ?
C12 C11 C9 118.6(2) . . ?
C12 C11 H11 120.7 . . ?
C11 C12 H12 119.6 . . ?
C11 C12 C13 120.9(2) . . ?
C13 C12 H12 119.6 . . ?
C12 C13 H13 118.6 . . ?
C14 C13 C12 122.7(2) . . ?
C14 C13 H13 118.6 . . ?
C10 C14 H14 121.9 . . ?
C13 C14 C10 116.3(2) . . ?
C13 C14 H14 121.9 . . ?
C16 C15 C20 120.0(2) . . ?
C16 C15 S1 119.14(17) . . ?
C20 C15 S1 120.86(18) . . ?
C15 C16 H16 120.3 . . ?
C17 C16 C15 119.5(2) . . ?
C17 C16 H16 120.3 . . ?
C16 C17 H17 119.2 . . ?
C16 C17 C18 121.6(2) . . ?
C18 C17 H17 119.2 . . ?
C17 C18 C21 120.7(3) . . ?
C19 C18 C17 117.6(2) . . ?
C19 C18 C21 121.7(2) . . ?
C18 C19 H19 119.0 . . ?
C20 C19 C18 121.9(2) . . ?
C20 C19 H19 119.0 . . ?
C15 C20 H20 120.3 . . ?
C19 C20 C15 119.4(2) . . ?
C19 C20 H20 120.3 . . ?
C18 C21 H21A 109.5 . . ?
C18 C21 H21B 109.5 . . ?
C18 C21 H21C 109.5 . . ?
H21A C21 H21B 109.5 . . ?
H21A C21 H21C 109.5 . . ?
H21B C21 H21C 109.5 . . ?
C8 N1 N2 106.30(15) . . ?
C10 N2 N1 110.90(15) . . ?
C10 N2 S1 127.17(14) . . ?
N1 N2 S1 117.62(14) . . ?
C2 O1 C1 118.02(18) . . ?
N2 S1 C15 105.48(9) . . ?
O2 S1 C15 108.97(9) . . ?
O2 S1 N2 104.40(10) . . ?
O3 S1 C15 109.46(12) . . ?
O3 S1 N2 106.23(10) . . ?
O3 S1 O2 121.10(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 H1A 0.9600 . ?
C1 H1B 0.9600 . ?
C1 H1C 0.9600 . ?
C1 O1 1.422(3) . ?
C2 C3 1.383(3) . ?
C2 C7 1.384(3) . ?
C2 O1 1.368(2) . ?
C3 H3 0.9300 . ?
C3 C4 1.387(3) . ?
C4 H4 0.9300 . ?
C4 C5 1.381(2) . ?
C5 C6 1.400(2) . ?
C5 C8 1.460(2) . ?
C6 H6 0.9300 . ?
C6 C7 1.367(3) . ?
C7 H7 0.9300 . ?
C8 C9 1.444(2) . ?
C8 N1 1.310(2) . ?
C9 C10 1.395(3) . ?
C9 C11 1.394(3) . ?
C10 C14 1.394(3) . ?
C10 N2 1.394(3) . ?
C11 H11 0.9300 . ?
C11 C12 1.370(3) . ?
C12 H12 0.9300 . ?
C12 C13 1.379(3) . ?
C13 H13 0.9300 . ?
C13 C14 1.366(3) . ?
C14 H14 0.9300 . ?
C15 C16 1.381(3) . ?
C15 C20 1.389(3) . ?
C15 S1 1.755(2) . ?
C16 H16 0.9300 . ?
C16 C17 1.376(3) . ?
C17 H17 0.9300 . ?
C17 C18 1.389(3) . ?
C18 C19 1.384(4) . ?
C18 C21 1.507(4) . ?
C19 H19 0.9300 . ?
C19 C20 1.368(4) . ?
C20 H20 0.9300 . ?
C21 H21A 0.9600 . ?
C21 H21B 0.9600 . ?
C21 H21C 0.9600 . ?
N1 N2 1.398(2) . ?
N2 S1 1.6599(17) . ?
O2 S1 1.4277(18) . ?
O3 S1 1.4127(17) . ?
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
C2 C3 C4 C5 0.3(3) . . . . ?
C3 C2 C7 C6 0.8(3) . . . . ?
C3 C2 O1 C1 -8.5(3) . . . . ?
C3 C4 C5 C6 1.1(3) . . . . ?
C3 C4 C5 C8 -178.52(17) . . . . ?
C4 C5 C6 C7 -1.5(3) . . . . ?
C4 C5 C8 C9 38.6(3) . . . . ?
C4 C5 C8 N1 -142.78(18) . . . . ?
C5 C6 C7 C2 0.6(3) . . . . ?
C5 C8 C9 C10 179.27(17) . . . . ?
C5 C8 C9 C11 3.3(3) . . . . ?
C5 C8 N1 N2 178.43(15) . . . . ?
C6 C5 C8 C9 -140.96(18) . . . . ?
C6 C5 C8 N1 37.6(3) . . . . ?
C7 C2 C3 C4 -1.2(3) . . . . ?
C7 C2 O1 C1 170.49(19) . . . . ?
C8 C5 C6 C7 178.07(17) . . . . ?
C8 C9 C10 C14 -178.16(19) . . . . ?
C8 C9 C10 N2 1.9(2) . . . . ?
C8 C9 C11 C12 176.3(2) . . . . ?
C8 N1 N2 C10 4.1(2) . . . . ?
C8 N1 N2 S1 162.44(13) . . . . ?
C9 C8 N1 N2 -2.8(2) . . . . ?
C9 C10 C14 C13 1.1(3) . . . . ?
C9 C10 N2 N1 -3.7(2) . . . . ?
C9 C10 N2 S1 -159.49(15) . . . . ?
C9 C11 C12 C13 0.1(3) . . . . ?
C10 C9 C11 C12 0.8(3) . . . . ?
C10 N2 S1 C15 76.1(2) . . . . ?
C10 N2 S1 O2 -38.7(2) . . . . ?
C10 N2 S1 O3 -167.76(18) . . . . ?
C11 C9 C10 C14 -1.5(3) . . . . ?
C11 C9 C10 N2 178.58(17) . . . . ?
C11 C12 C13 C14 -0.5(4) . . . . ?
C12 C13 C14 C10 -0.2(4) . . . . ?
C14 C10 N2 N1 176.4(2) . . . . ?
C14 C10 N2 S1 20.6(3) . . . . ?
C15 C16 C17 C18 -0.4(3) . . . . ?
C16 C15 C20 C19 -1.5(3) . . . . ?
C16 C15 S1 N2 -97.73(17) . . . . ?
C16 C15 S1 O2 13.86(19) . . . . ?
C16 C15 S1 O3 148.34(16) . . . . ?
C16 C17 C18 C19 -1.5(3) . . . . ?
C16 C17 C18 C21 178.0(2) . . . . ?
C17 C18 C19 C20 1.9(3) . . . . ?
C18 C19 C20 C15 -0.4(3) . . . . ?
C20 C15 C16 C17 1.9(3) . . . . ?
C20 C15 S1 N2 81.10(17) . . . . ?
C20 C15 S1 O2 -167.30(16) . . . . ?
C20 C15 S1 O3 -32.82(18) . . . . ?
C21 C18 C19 C20 -177.6(2) . . . . ?
N1 C8 C9 C10 0.6(2) . . . . ?
N1 C8 C9 C11 -175.4(2) . . . . ?
N1 N2 S1 C15 -78.32(16) . . . . ?
N1 N2 S1 O2 166.88(14) . . . . ?
N1 N2 S1 O3 37.82(19) . . . . ?
N2 C10 C14 C13 -178.9(2) . . . . ?
O1 C2 C3 C4 177.74(17) . . . . ?
O1 C2 C7 C6 -178.28(17) . . . . ?
S1 C15 C16 C17 -179.21(16) . . . . ?
S1 C15 C20 C19 179.63(16) . . . . ?
