Rh(II)-Catalyzed Denitrogenative Reaction of N-Sulfonyl-1,2,3-triazoles with Isatins for the Construction of Indigoids.
Pal, Kuntal; Shukla, Rahul K.; Volla, Chandra M. R.; Organic letters 19 (2017) 5764–5767; doi:10.1021/acs.orglett.7b02697

data_1547766
_publ_section_title
;
 Rh(II)-Catalyzed Denitrogenative Reaction of N-Sulfonyl-1,2,3-triazoles
 with Isatins for the Construction of Indigoids.
;
_journal_issue                   21
_journal_name_full               'Organic letters'
_journal_page_first              5764
_journal_page_last               5767
_journal_paper_doi               10.1021/acs.orglett.7b02697
_journal_volume                  19
_journal_year                    2017
_chemical_formula_moiety         'C24 H20 N2 O5 S'
_chemical_formula_sum            'C24 H20 Cl0 N2 O5 S'
_chemical_formula_weight         448.48
_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_space_group_name_Hall  '-P 2ac 2ab'
_symmetry_space_group_name_H-M   'P b c a'
_atom_sites_solution_hydrogens   mixed
_audit_creation_date             2017-10-14
_audit_creation_method
;
Olex2 1.2-alpha
(compiled 2015.10.28 svn.r3245 for OlexSys, GUI svn.r5128)
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   11.3088(7)
_cell_length_b                   13.4942(7)
_cell_length_c                   27.4368(13)
_cell_measurement_reflns_used    4384
_cell_measurement_temperature    150(2)
_cell_measurement_theta_max      31.0410
_cell_measurement_theta_min      2.3140
_cell_volume                     4186.9(4)
_computing_cell_refinement       'CrysAlisPro 1.171.38.43 (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.38.43 (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.43 (Rigaku OD, 2015)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'SHELXL-2014/7 (Sheldrick, 2014)'
_diffrn_ambient_temperature      150(2)
_diffrn_detector                 'CCD plate'
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_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    -98.00  19.00   0.50    8.00    --  -20.00 -72.00  36.00  234
  2  \w    -62.00  -4.00   0.50    8.00    --  -20.00   0.00  36.00  116
;
_diffrn_measurement_device       'abstract diffractometer'
_diffrn_measurement_device_type
'dtrek-CrysAlisPro-abstract goniometer imported rigaku-d*trek images'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0619446000
_diffrn_orient_matrix_UB_12      -0.0070838000
_diffrn_orient_matrix_UB_13      0.0019404000
_diffrn_orient_matrix_UB_21      0.0061609000
_diffrn_orient_matrix_UB_22      0.0090186000
_diffrn_orient_matrix_UB_23      -0.0253407000
_diffrn_orient_matrix_UB_31      0.0074065000
_diffrn_orient_matrix_UB_32      0.0513234000
_diffrn_orient_matrix_UB_33      0.0047371000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0728
_diffrn_reflns_av_unetI/netI     0.0747
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_l_max       32
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_number            12875
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_theta_full        24.995
_diffrn_reflns_theta_max         24.995
_diffrn_reflns_theta_min         2.334
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_source_type              'Enhance (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    0.195
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.47289
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.38.43 (Rigaku Oxford Diffraction, 2015)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            red
_exptl_crystal_colour_primary    red
_exptl_crystal_density_diffrn    1.423
_exptl_crystal_description       plate
_exptl_crystal_F_000             1872
_exptl_crystal_size_max          0.247
_exptl_crystal_size_mid          0.177
_exptl_crystal_size_min          0.042
_refine_diff_density_max         0.704
_refine_diff_density_min         -0.562
_refine_diff_density_rms         0.091
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.053
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     291
_refine_ls_number_reflns         3675
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.053
_refine_ls_R_factor_all          0.0890
_refine_ls_R_factor_gt           0.0618
_refine_ls_shift/su_max          0.009
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0706P)^2^+3.7062P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1440
_refine_ls_wR_factor_ref         0.1649
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2718
_reflns_number_total             3675
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            ol7b02697_si_002.cif
_cod_data_source_block           cmrv
_cod_depositor_comments          'Adding full bibliography for 1547766.cif.'
_cod_original_cell_volume        4187.0(4)
_cod_database_code               1547766
_chemical_oxdiff_formula         C24H20N2O5S1
_reflns_odcompleteness_completeness 91.27
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     31.10
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All N(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Riding coordinates:
 N008(H008)
2.b Aromatic/amide H refined with riding coordinates:
 N007(H007), C00C(H00C), C00F(H00F), C00H(H00H), C00J(H00J), C00K(H00K),
 C00L(H00L), C00O(H00O), C00Q(H00Q), C00R(H00R), C00S(H00S), C00T(H00T),
 C00V(H00V)
2.c Idealised Me refined as rotating group:
 C00U(H00A,H00B,H00D), C00W(H00E,H00G,H00I)
;
_shelx_res_checksum              38052
_shelx_hkl_checksum              57001
_shelx_shelxl_version_number     2014/7
_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
- Detector area scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.653
_oxdiff_exptl_absorpt_empirical_full_min 0.647