Palladium-Catalyzed Synthesis of 1H-Indenes and Phthalimides via Isocyanide Insertion.
Wang, Xu; Xiong, Wenfang; Huang, Yubing; Zhu, Jiayi; Hu, Qiong; Wu, Wanqing; Jiang, Huanfeng; Organic letters 19 (2017) 5818–5821; doi:10.1021/acs.orglett.7b02771

data_1547781
_publ_section_title
;
 Palladium-Catalyzed Synthesis of 1H-Indenes and Phthalimides via
 Isocyanide Insertion.
;
_journal_issue                   21
_journal_name_full               'Organic letters'
_journal_page_first              5818
_journal_page_last               5821
_journal_paper_doi               10.1021/acs.orglett.7b02771
_journal_volume                  19
_journal_year                    2017
_chemical_absolute_configuration ukn
_chemical_formula_moiety         'C21 H21 N3'
_chemical_formula_sum            'C21 H21 N3'
_chemical_formula_weight         315.41
_space_group_crystal_system      monoclinic
_space_group_IT_number           4
_space_group_name_Hall           'P 2yb'
_space_group_name_H-M_alt        'P 1 21 1'
_symmetry_space_group_name_Hall  'P 2yb'
_symmetry_space_group_name_H-M   'P 1 21 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2016-12-07
_audit_creation_method
;
Olex2 1.2
(compiled 2016.11.30 svn.r3356 for OlexSys, GUI svn.r5269)
;
_audit_update_record
;
2017-05-24 deposited with the CCDC.
2017-05-24 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 112.655(2)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   9.6502(2)
_cell_length_b                   10.11860(10)
_cell_length_c                   9.8060(2)
_cell_measurement_reflns_used    2342
_cell_measurement_temperature    100.00(10)
_cell_measurement_theta_max      73.0080
_cell_measurement_theta_min      4.3620
_cell_volume                     883.64(3)
_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 (Sheldrick, 2015)'
_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 1.0000
_diffrn_measured_fraction_theta_max 0.6463
_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    -74.00  31.00   1.00    1.00    --  -40.98  77.00  60.00  105
  2  \w   -101.00 -20.00   1.00    1.00    --  -40.98 -37.00 120.00   81
  3  \w     53.00  90.00   1.00    1.00    --   40.98-125.00-150.00   37
  4  \w     35.00 104.00   1.00    1.17    --  106.95 -94.00   0.00   69
  5  \w     43.00 130.00   1.00    1.17    --  106.95 -45.00  30.00   87
  6  \w     53.00 109.00   1.00    1.17    --  106.95 -94.00 150.00   56
  7  \w     80.00 174.00   1.00    1.17    --  106.95  30.00-150.00   94
  8  \w    152.00 178.00   1.00    1.17    --  106.95 125.00  30.00   26
  9  \w    115.00 144.00   1.00    1.17    --  106.95 125.00  30.00   29
;
_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      -0.0063934000
_diffrn_orient_matrix_UB_12      0.0069501000
_diffrn_orient_matrix_UB_13      -0.1592758000
_diffrn_orient_matrix_UB_21      0.1642036000
_diffrn_orient_matrix_UB_22      0.0478857000
_diffrn_orient_matrix_UB_23      0.0590316000
_diffrn_orient_matrix_UB_31      0.0540525000
_diffrn_orient_matrix_UB_32      -0.1443323000
_diffrn_orient_matrix_UB_33      0.0117903000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0177
_diffrn_reflns_av_unetI/netI     0.0282
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.963
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       9
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_number            3109
_diffrn_reflns_point_group_measured_fraction_full 0.681
_diffrn_reflns_point_group_measured_fraction_max 0.647
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         73.419
_diffrn_reflns_theta_min         4.887
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.548
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.87785
_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            red
_exptl_crystal_density_diffrn    1.185
_exptl_crystal_description       block
_exptl_crystal_F_000             336
_exptl_crystal_size_max          0.3
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.2
_refine_diff_density_max         0.125
_refine_diff_density_min         -0.193
_refine_diff_density_rms         0.044
_refine_ls_abs_structure_details
;
 Flack x determined using 478 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.2(4)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.077
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     221
_refine_ls_number_reflns         2307
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.076
_refine_ls_R_factor_all          0.0334
_refine_ls_R_factor_gt           0.0325
_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^)+(0.0510P)^2^+0.0570P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0820
_refine_ls_wR_factor_ref         0.0833
_reflns_Friedel_coverage         0.268
_reflns_Friedel_fraction_full    0.322
_reflns_Friedel_fraction_max     0.291
_reflns_number_gt                2254
_reflns_number_total             2307
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            ol7b02771_si_002.cif
_cod_data_source_block           exp_121
_cod_depositor_comments          'Adding full bibliography for 1547781.cif.'
_cod_database_code               1547781
_shelx_estimated_absorpt_t_max   0.898
_shelx_estimated_absorpt_t_min   0.853
_reflns_odcompleteness_completeness 100.00
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_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 Aromatic/amide H refined with riding coordinates:
 N001(H001), C005(H005), C00A(H00A), C00D(H00D), C00E(H00E), C00F(H00F),
 C00G(H00G), C00J(H00J), C00K(H00K)
2.b Idealised Me refined as rotating group:
 C00L(H00B,H00C,H00H), C00M(H00I,H00L,H00M), C00N(H00N,H00O,H00P), C00O(H00Q,
 H00R,H00S)
;
_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
;
_oxdiff_exptl_absorpt_empirical_full_max 1.238
_oxdiff_exptl_absorpt_empirical_full_min 0.630