Silver-Catalyzed Radical-Involved Cascade Cyclization of Diphenylphosphine with Cinnamamides: Access to 2-Phosphinoyl-3H-pyrrolo[1,2-a]indoles.
Xu, Jian; Yu, Xiaoxia; Song, Qiuling; Organic letters 19 (2017) 980–983; doi:10.1021/acs.orglett.6b03713

data_1545430
_publ_section_title
;
 Silver-Catalyzed Radical-Involved Cascade Cyclization of
 Diphenylphosphine with Cinnamamides: Access to
 2-Phosphinoyl-3H-pyrrolo[1,2-a]indoles.
;
_journal_issue                   5
_journal_name_full               'Organic letters'
_journal_page_first              980
_journal_page_last               983
_journal_paper_doi               10.1021/acs.orglett.6b03713
_journal_volume                  19
_journal_year                    2017
_chemical_formula_moiety         'C35 H26 N O2 P'
_chemical_formula_sum            'C35 H26 N O2 P'
_chemical_formula_weight         523.54
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2yn'
_space_group_name_H-M_alt        'P 1 21/n 1'
_symmetry_space_group_name_Hall  '-P 2yn'
_symmetry_space_group_name_H-M   'P 1 21/n 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     iterative
_audit_creation_date             2016-10-20
_audit_creation_method
;
Olex2 1.2
(compiled 2014.03.20 svn.r2914 for OlexSys, GUI svn.r4816)
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   10.697(3)
_cell_length_b                   14.116(7)
_cell_length_c                   18.102(9)
_cell_measurement_reflns_used    1647
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      22.3730
_cell_measurement_theta_min      3.6570
_cell_volume                     2733(2)
_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  'ShelXL (Sheldrick, 2008)'
_computing_structure_solution    'olex2.solve (Bourhis et al., 2013)'
_diffrn_ambient_temperature      293(2)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 16.1213
_diffrn_detector_type            Eos
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.818
_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      0.0295355000
_diffrn_orient_matrix_UB_12      0.0170070000
_diffrn_orient_matrix_UB_13      -0.0328391000
_diffrn_orient_matrix_UB_21      -0.0110417000
_diffrn_orient_matrix_UB_22      0.0472802000
_diffrn_orient_matrix_UB_23      0.0117001000
_diffrn_orient_matrix_UB_31      0.0585474000
_diffrn_orient_matrix_UB_32      0.0003388000
_diffrn_orient_matrix_UB_33      0.0176787000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0765
_diffrn_reflns_av_unetI/netI     0.1387
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.818
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       19
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_limit_l_min       -24
_diffrn_reflns_number            12279
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.818
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         29.627
_diffrn_reflns_theta_min         2.886
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_source_type              'Enhance (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    0.134
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.62387
_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_colour            white
_exptl_crystal_density_diffrn    1.272
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             1096
_exptl_crystal_size_max          0.5
_exptl_crystal_size_mid          0.4
_exptl_crystal_size_min          0.3
_refine_diff_density_max         0.286
_refine_diff_density_min         -0.262
_refine_diff_density_rms         0.054
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.975
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     352
_refine_ls_number_reflns         6296
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.975
_refine_ls_R_factor_all          0.1866
_refine_ls_R_factor_gt           0.0741
_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^)+(0.0599P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1436
_refine_ls_wR_factor_ref         0.2004
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2613
_reflns_number_total             6296
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            ol6b03713_si_002.cif
_cod_data_source_block           exp_2770
_cod_database_code               1545430
_shelxl_version_number           2014-1
_reflns_odcompleteness_completeness 99.71
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     26.32
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
2.a Ternary CH refined with riding coordinates:
 C33(H33), C14(H14)
2.b Aromatic/amide H refined with riding coordinates:
 C36(H36), C23(H23), C1(H1), C37(H37), C39(H39), C5(H5), C29(H29), C3(H3),
 C32(H32), C31(H31), C9(H9), C12(H12), C19(H19), C35(H35), C27(H27), C22(H22),
 C2(H2), C4(H4), C30(H30), C10(H10), C11(H11), C13(H13), C38(H38), C24(H24)
;
_oxdiff_exptl_absorpt_empirical_details
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.339
_oxdiff_exptl_absorpt_empirical_full_min 0.662