Silver-Catalyzed Oxidative Cyclization of Propargylamide-Substituted Indoles: Synthesis of Phosphorated Indoloazepinones Derivatives.
Hua, Hui-Liang; Zhang, Bo-Sheng; He, Yu-Tao; Qiu, Yi-Feng; Wu, Xin-Xing; Xu, Peng-Fei; Liang, Yong-Min; Organic letters 18 (2016) 216–219; doi:10.1021/acs.orglett.5b03329

data_1540740
_publ_section_title
;
 Silver-Catalyzed Oxidative Cyclization of Propargylamide-Substituted
 Indoles: Synthesis of Phosphorated Indoloazepinones Derivatives.
;
_journal_issue                   2
_journal_name_full               'Organic letters'
_journal_page_first              216
_journal_page_last               219
_journal_paper_doi               10.1021/acs.orglett.5b03329
_journal_volume                  18
_journal_year                    2016
_chemical_formula_moiety         'C32 H27 N2 O2 P'
_chemical_formula_sum            'C32 H27 N2 O2 P'
_chemical_formula_weight         502.53
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2ybc'
_space_group_name_H-M_alt        'P 1 21/c 1'
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 1 21/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_date             2015-07-01
_audit_creation_method
;
Olex2 1.2
(compiled 2014.11.28 svn.r3106 for OlexSys, GUI svn.r4959)
;
_cell_angle_alpha                90.00
_cell_angle_beta                 106.794(6)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   14.0310(7)
_cell_length_b                   8.9510(3)
_cell_length_c                   20.9862(11)
_cell_measurement_reflns_used    1840
_cell_measurement_temperature    293.33(10)
_cell_measurement_theta_max      27.1280
_cell_measurement_theta_min      3.8930
_cell_volume                     2523.3(2)
_computing_cell_refinement
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.33 (release 27-03-2014 CrysAlis171 .NET)
(compiled Mar 27 2014,17:12:48)
;
_computing_data_collection
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.33 (release 27-03-2014 CrysAlis171 .NET)
(compiled Mar 27 2014,17:12:48)
;
_computing_data_reduction
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.33 (release 27-03-2014 CrysAlis171 .NET)
(compiled Mar 27 2014,17:12:48)
;
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2008)'
_computing_structure_solution    'ShelXS (Sheldrick, 2008)'
_diffrn_ambient_environment      air
_diffrn_ambient_temperature      293.33(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 16.0733
_diffrn_detector_type            Eos
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_details
;
  1 omega  -15.00   16.20   1.2000    3.0000
omega____ theta____ kappa____ phi______ frames
    -      -16.9916  -99.0000  -60.0000 26

  2 omega  -46.00   48.80   1.2000    3.0000
omega____ theta____ kappa____ phi______ frames
    -       20.5854  -19.0000   90.0000 79

  3 omega  -40.00   46.40   1.2000    3.0000
omega____ theta____ kappa____ phi______ frames
    -       20.5854  -38.0000    0.0000 72
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, Eos'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_UB_11      -0.0166462000
_diffrn_orient_matrix_UB_12      0.0399158000
_diffrn_orient_matrix_UB_13      0.0239794000
_diffrn_orient_matrix_UB_21      0.0382548000
_diffrn_orient_matrix_UB_22      -0.0332519000
_diffrn_orient_matrix_UB_23      0.0258525000
_diffrn_orient_matrix_UB_31      0.0323401000
_diffrn_orient_matrix_UB_32      0.0598584000
_diffrn_orient_matrix_UB_33      -0.0016388000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0476
_diffrn_reflns_av_unetI/netI     0.0888
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       25
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_number            9390
_diffrn_reflns_theta_full        25.50
_diffrn_reflns_theta_max         26.02
_diffrn_reflns_theta_min         3.66
_diffrn_source                   'SuperNova (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    0.143
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.98073
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.33 (release 27-03-2014 CrysAlis171 .NET)
(compiled Mar 27 2014,17:12:48)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            'clear light yellow'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.323
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             1056
_exptl_crystal_size_max          0.34
_exptl_crystal_size_mid          0.33
_exptl_crystal_size_min          0.31
_refine_diff_density_max         0.313
_refine_diff_density_min         -0.401
_refine_diff_density_rms         0.063
_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     336
_refine_ls_number_reflns         4954
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.053
_refine_ls_R_factor_all          0.0916
_refine_ls_R_factor_gt           0.0575
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0434P)^2^+0.4161P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1134
_refine_ls_wR_factor_ref         0.1396
_reflns_number_gt                3343
_reflns_number_total             4954
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ol5b03329_si_002.cif
_cod_data_source_block           huahl0701
_cod_depositor_comments          'Adding full bibliography for 1540740.cif.'
_cod_database_code               1540740
_reflns_odcompleteness_completeness 99.64
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     26.32
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Secondary CH2 refined with riding coordinates:
 C11(H11A,H11B)
2.b Aromatic/amide H refined with riding coordinates:
 C2(H2), C3(H3), C4(H4), C5(H5), C16(H16), C17(H17), C18(H18), C19(H19),
 C20(H20), C22(H22), C23(H23), C24(H24), C25(H25), C26(H26), C28(H28), C29(H29),
  C30(H30), C31(H31), C32(H32)
2.c Idealised Me refined as rotating group:
 C13(H13A,H13B,H13C), C14(H14A,H14B,H14C)
;
_olex2_date_sample_data_collection 2015-07-01
_olex2_submission_special_instructions 'No special instructions were received'