Oxidant-controlled divergent transformations of 3-aminoindazoles for the synthesis of pyrimido[1,2-b]-indazoles and aromatic nitrile-derived dithioacetals
Zhou, Yao; Lou, Yixian; Wang, Ya; Song, Qiuling; Organic Chemistry Frontiers 6 (2019) 3355–; doi:10.1039/C9QO00847K

data_1555082
_publ_section_title
;
 Oxidant-controlled divergent transformations of 3-aminoindazoles for the
 synthesis of pyrimido[1,2-b]-indazoles and aromatic nitrile-derived
 dithioacetals
;
_journal_issue                   19
_journal_name_full               'Organic Chemistry Frontiers'
_journal_page_first              3355
_journal_paper_doi               10.1039/C9QO00847K
_journal_volume                  6
_journal_year                    2019
_chemical_formula_moiety         'C19 H17 N O S2'
_chemical_formula_sum            'C19 H17 N O S2'
_chemical_formula_weight         339.48
_space_group_crystal_system      orthorhombic
_space_group_IT_number           61
_space_group_name_Hall           '-P 2ac 2ab'
_space_group_name_H-M_alt        'P b c a'
_symmetry_Int_Tables_number      61
_atom_sites_solution_primary     dual
_audit_block_doi                 10.5517/ccdc.csd.cc20y0ff
_audit_creation_date             2018-10-23
_audit_creation_method
;
Olex2 1.2
(compiled 2017.03.28 svn.r3405 for OlexSys, GUI svn.r5335)
;
_audit_update_record
;
2018-10-23 deposited with the CCDC.	2019-08-09 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   10.1327(10)
_cell_length_b                   12.0719(14)
_cell_length_c                   28.967(3)
_cell_measurement_reflns_used    1952
_cell_measurement_temperature    298
_cell_measurement_theta_max      27.7390
_cell_measurement_theta_min      4.0270
_cell_volume                     3543.3(7)
_computing_cell_refinement       'CrysAlisPro 1.171.38.41 (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.38.41 (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.41 (Rigaku OD, 2015)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'olex2.refine (Bourhis et al., 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_diffrn_ambient_temperature      298
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 8.0606
_diffrn_detector_type            Eos
_diffrn_measured_fraction_theta_full 0.9981
_diffrn_measured_fraction_theta_max 0.9981
_diffrn_measurement_details
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  t~exp~   \w     \q     \k     \f   Frames
  1  \w    -10.00  62.90   0.30   10.50    --   15.49  77.00 150.00  243
  2  \w    -41.00  -2.00   0.30   10.50    --  -16.28  19.00 -30.00  130
  3  \w    -17.00  23.20   0.30   10.50    --  -16.28 -99.00  30.00  134
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'Xcalibur, Eos, Gemini'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0610034000
_diffrn_orient_matrix_UB_12      -0.0131281000
_diffrn_orient_matrix_UB_13      0.0106809000
_diffrn_orient_matrix_UB_21      -0.0243822000
_diffrn_orient_matrix_UB_22      0.0203635000
_diffrn_orient_matrix_UB_23      0.0213500000
_diffrn_orient_matrix_UB_31      -0.0241773000
_diffrn_orient_matrix_UB_32      -0.0535234000
_diffrn_orient_matrix_UB_33      0.0054531000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0916
_diffrn_reflns_av_unetI/netI     0.1500
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -5
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       24
_diffrn_reflns_limit_l_min       -39
_diffrn_reflns_number            10871
_diffrn_reflns_theta_full        24.9985
_diffrn_reflns_theta_max         25.00
_diffrn_reflns_theta_min         3.37
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_source_type              'Enhance (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    0.304
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.09698
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.38.41 (Rigaku Oxford Diffraction, 2015)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_density_diffrn    1.2727
_exptl_crystal_description       block
_exptl_crystal_F_000             1426.4823
_refine_diff_density_max         0.8745
_refine_diff_density_min         -0.5269
_refine_diff_density_rms         0.1398
_refine_ls_d_res_high            0.8409
_refine_ls_d_res_low             6.0492
_refine_ls_goodness_of_fit_ref   0.8505
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_constraints    28
_refine_ls_number_parameters     211
_refine_ls_number_reflns         3111
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.8505
_refine_ls_R_factor_all          0.1198
_refine_ls_R_factor_gt           0.0634
_refine_ls_shift/su_max          0.0000
_refine_ls_shift/su_mean         0.0000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.1P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1463
_refine_ls_wR_factor_ref         0.1848
_reflns_Friedel_coverage         0.0
_reflns_limit_h_max              12
_reflns_limit_h_min              0
_reflns_limit_k_max              14
_reflns_limit_k_min              0
_reflns_limit_l_max              34
_reflns_limit_l_min              0
_reflns_number_gt                1790
_reflns_number_total             3111
_reflns_threshold_expression     I>=2u(I)
_cod_data_source_file            c9qo00847k2.cif
_cod_data_source_block           exp_5898
_cod_depositor_comments
;

2025-06-17
Z value and formula fixed to values more according to usual
chemical conventions.                 miguel
;
_cod_original_formula_moiety     '0.5(C19 H17 N O S2)'
_cod_original_formula_sum        'C9.5 H8.5 N0.5 O0.5 S'
_cod_original_formula_units_Z    16
_cod_original_formula_weight     169.74
_cod_database_code               1555082
_reflns_odcompleteness_completeness 99.54
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     26.32
_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:
 C00C(H00C), C00H(H00H), C00K(H00K), C00A(H00A), C00I(H00I), C00J(H00J),
 C00G(H00G), C009(H009)
2.b Idealised Me refined as rotating group:
 C00L(H00b,H00d,H00e), C00M(H00f,H00l,H00m), C00N(H00n,H00o,H00p)
;
_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 3.657
_oxdiff_exptl_absorpt_empirical_full_min 0.354