Ag(I)/PPh3-Catalyzed Diastereoselective Syntheses of Spiro[indole-3,4'-piperidine] Derivatives via Cycloisomerizations of Tryptamine-Ynamides
Chen, Yanyu; Wang, Zhaobo; Zhao, Wutong; Sun, Shitao; Yang, Lu; Zhang, Junpeng; Zhang, Di; Cheng, Mao-sheng; Lin, Bin; Liu, Yongxiang; Chemical Communications  (2022) –; doi:10.1039/D1CC07298F

data_7129692
_publ_section_title
;
 Ag(I)/PPh3-Catalyzed Diastereoselective Syntheses of
 Spiro[indole-3,4'-piperidine] Derivatives via Cycloisomerizations of
 Tryptamine-Ynamides
;
_journal_name_full               'Chemical Communications'
_journal_paper_doi               10.1039/D1CC07298F
_journal_year                    2022
_chemical_absolute_configuration ad
_chemical_formula_sum            'C20 H16 N2 O2'
_chemical_formula_weight         316.35
_space_group_crystal_system      orthorhombic
_space_group_IT_number           19
_space_group_name_Hall           'P 2ac 2ab'
_space_group_name_H-M_alt        'P 21 21 21'
_atom_sites_solution_hydrogens   geom
_audit_update_record
;
2021-08-23 deposited with the CCDC.	2022-02-09 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   7.4296(3)
_cell_length_b                   7.9065(3)
_cell_length_c                   27.5593(12)
_cell_measurement_reflns_used    9050
_cell_measurement_temperature    153.(2)
_cell_measurement_theta_max      58.3146
_cell_measurement_theta_min      5.8219
_cell_volume                     1618.89(11)
_computing_cell_refinement       'SAINT V8.40A (Bruker Nano, Inc., 2019)'
_computing_data_reduction        'SAINT V8.40A (Bruker Nano, Inc., 2019)'
_computing_molecular_graphics    'shelXle (C.B. Huebschle, rev 958)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_diffrn_ambient_temperature      153.(2)
_diffrn_detector_area_resol_mean 7.3910
_diffrn_measured_fraction_theta_full 0.993
_diffrn_measured_fraction_theta_max 0.993
_diffrn_measurement_device_type  'Bruker D8 QUEST PHOTON II'
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0197
_diffrn_reflns_av_unetI/netI     0.0135
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       30
_diffrn_reflns_limit_l_min       -30
_diffrn_reflns_number            10097
_diffrn_reflns_theta_full        58.31
_diffrn_reflns_theta_max         58.31
_diffrn_reflns_theta_min         5.82
_exptl_absorpt_coefficient_mu    0.683
_exptl_absorpt_correction_T_max  0.88
_exptl_absorpt_correction_T_min  0.76
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2016/2 - Bruker AXS area detector scaling and absorption correction
;
_exptl_crystal_density_diffrn    1.298
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             664
_exptl_crystal_size_max          0.300
_exptl_crystal_size_mid          0.300
_exptl_crystal_size_min          0.200
_refine_diff_density_max         0.103
_refine_diff_density_min         -0.134
_refine_ls_abs_structure_details
;

Flack x determined using 898 quotients [(I+)-(I-)]/[(I+)+(I-)]
(Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.06(4)
_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     217
_refine_ls_number_reflns         2261
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.096
_refine_ls_R_factor_all          0.0251
_refine_ls_R_factor_gt           0.0245
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0337P)^2^+0.2292P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0619
_refine_ls_wR_factor_ref         0.0623
_reflns_number_gt                2238
_reflns_number_total             2261
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d1cc07298f2.cif
_cod_data_source_block           CYY0129_20210327
_cod_depositor_comments
;
The following automatic conversions were performed:

data item '_exptl_absorpt_correction_type' value 'Multi-Scan' was
changed to 'multi-scan' in accordance with the
/home/data/users/saulius/crontab/automatic-downloads/rss-feeds/RSC/lib/dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.2 last updated on
2011-04-26.

Automatic conversion script
Id: cif_fix_values 7556 2019-12-06 15:28:31Z antanas 
;
_cod_database_code               7129692
_shelx_res_checksum              365