Copper-catalyzed decarboxylative propargylation/hydroamination reactions: access to C3 β-ketoester-functionalized indoles.
Wang, Sasa; Liu, Miao; Chen, Xinzheng; Wang, Huifei; Zhai, Hongbin; Chemical communications (Cambridge, England) 54 (2018) 8375–8378; doi:10.1039/c8cc04499f

data_7121920
_publ_section_title
;
 Copper-catalyzed decarboxylative propargylation/hydroamination reactions:
 access to C3 \b-ketoester-functionalized indoles.
;
_journal_issue                   60
_journal_name_full               'Chemical communications (Cambridge, England)'
_journal_page_first              8375
_journal_page_last               8378
_journal_paper_doi               10.1039/c8cc04499f
_journal_volume                  54
_journal_year                    2018
_chemical_formula_moiety         'C25 H29 N O5 S'
_chemical_formula_sum            'C25 H29 N O5 S'
_chemical_formula_weight         455.55
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   geom
_audit_creation_date             2018-03-02
_audit_creation_method
;
Olex2 1.2
(compiled 2017.08.10 svn.r3458 for OlexSys, GUI svn.r5381)
;
_audit_update_record
;
2018-04-17 deposited with the CCDC.
2018-07-04 downloaded from the CCDC.
;
_cell_angle_alpha                92.269(5)
_cell_angle_beta                 102.450(6)
_cell_angle_gamma                100.774(5)
_cell_formula_units_Z            2
_cell_length_a                   9.0009(6)
_cell_length_b                   9.4814(5)
_cell_length_c                   14.6222(10)
_cell_measurement_reflns_used    3203
_cell_measurement_temperature    100.00(10)
_cell_measurement_theta_max      73.0200
_cell_measurement_theta_min      3.0940
_cell_volume                     1192.89(14)
_computing_cell_refinement       'CrysAlisPro 1.171.38.43f (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.38.43f (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.43f (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    'SHELXT 2014/5 (Sheldrick, 2014)'
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      100.00(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 5.2684
_diffrn_detector_type            AtlasS2
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.960
_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     19.00  46.00   1.00    1.01    --   40.98  57.00   0.00   27
  2  \w     88.00 113.00   1.00    1.01    --   40.98  57.00   0.00   25
  3  \w    106.00 133.00   1.00    2.00    --  107.58 125.00  30.00   27
  4  \w     83.00 178.00   1.00    2.00    --  107.58  45.00 120.00   95
  5  \w     74.00 101.00   1.00    2.00    --  107.58 -95.00  90.00   27
  6  \w     69.00 122.00   1.00    2.00    --  107.58-125.00   0.00   53
  7  \w     38.00  65.00   1.00    2.00    --  107.58-125.00   0.00   27
  8  \w     39.00 139.00   1.00    2.00    --  107.58 -77.00 -30.00  100
  9  \w     58.00 168.00   1.00    2.00    --  107.58  15.00 -90.00  110
 10  \w     40.00 130.00   1.00    2.00    --  107.58 -61.00-180.00   90
 11  \w     42.00 133.00   1.00    2.00    --  107.58 -30.00 -60.00   91
 12  \w     36.00 100.00   1.00    2.00    --  107.58 -30.00  90.00   64
 13  \w     26.00 108.00   1.00    2.00    --  107.58 -95.00 150.00   82
 14  \w     30.00  90.00   1.00    1.01    --   40.98-125.00-150.00   60
 15  \w    -31.00  64.00   1.00    1.01    --   40.98 -57.00-150.00   95
 16  \w    -67.00  32.00   1.00    1.01    --  -40.98  57.00 120.00   99
 17  \w   -109.00 -19.00   1.00    1.01    --  -40.98 -57.00 -30.00   90
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, AtlasS2'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0225993000
_diffrn_orient_matrix_UB_12      -0.1213568000
_diffrn_orient_matrix_UB_13      0.0654986000
_diffrn_orient_matrix_UB_21      0.0931743000
_diffrn_orient_matrix_UB_22      0.1125984000
_diffrn_orient_matrix_UB_23      0.0806652000
_diffrn_orient_matrix_UB_31      -0.1510457000
_diffrn_orient_matrix_UB_32      0.0119161000
_diffrn_orient_matrix_UB_33      0.0304263000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0421
_diffrn_reflns_av_unetI/netI     0.0573
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.960
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            7966
_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.960
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         73.783
_diffrn_reflns_theta_min         3.106
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    1.497
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.67652
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.38.43f (Rigaku Oxford Diffraction, 2015)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.268
_exptl_crystal_description       block
_exptl_crystal_F_000             484
_exptl_crystal_size_max          0.13
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.11
_refine_diff_density_max         0.804
_refine_diff_density_min         -0.555
_refine_diff_density_rms         0.091
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.096
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     297
_refine_ls_number_reflns         4642
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.096
_refine_ls_R_factor_all          0.0758
_refine_ls_R_factor_gt           0.0655
_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/[\s^2^(Fo^2^)+(0.0913P)^2^+0.8856P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1737
_refine_ls_wR_factor_ref         0.1830
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3916
_reflns_number_total             4642
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c8cc04499f2.cif
_cod_data_source_block           exp_1275
_cod_depositor_comments          'Adding full bibliography for 7121920.cif.'
_cod_original_cell_volume        1192.88(13)
_cod_database_code               7121920
_shelx_shelxl_version_number     2017/1
_reflns_odcompleteness_completeness 99.74
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_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, All O(H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C5(H5), C12(H12), C11(H11), C2(H2), C15(H15), C3(H3), C14(H14)
2.b Idealised Me refined as rotating group:
 C20(H20A,H20B,H20C), C9(H9A,H9B,H9C), C16(H16A,H16B,H16C), C17(H17A,H17B,
 H17C), C23(H23A,H23B,H23C), C24(H24A,H24B,H24C), C25(H25A,H25B,H25C)
2.c Idealised tetrahedral OH refined as rotating group:
 O1(H1)
;
_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 1.469
_oxdiff_exptl_absorpt_empirical_full_min 0.574