Exploring Gold Catalysis in a 1,6-Conjugate Addition/Domino Electrophilic Cyclization Cascade: Synthesis of Cyclohepta[ b]indoles.
Jadhav, Abhijeet S.; Pankhade, Yogesh A.; Vijaya Anand, Ramasamy; The Journal of organic chemistry 83 (2018) 8615–8626; doi:10.1021/acs.joc.8b00607

data_4035555
_publ_section_title
;
 Exploring Gold Catalysis in a 1,6-Conjugate Addition/Domino Electrophilic
 Cyclization Cascade: Synthesis of Cyclohepta[ b]indoles.
;
_journal_issue                   15
_journal_name_full               'The Journal of organic chemistry'
_journal_page_first              8615
_journal_page_last               8626
_journal_paper_doi               10.1021/acs.joc.8b00607
_journal_volume                  83
_journal_year                    2018
_chemical_formula_moiety         'C37 H37 N O'
_chemical_formula_sum            'C37 H37 N O'
_chemical_formula_weight         511.68
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   difmap
_audit_creation_date             2017-08-15
_audit_creation_method
;
Olex2 1.2
(compiled 2017.08.10 svn.r3458 for OlexSys, GUI svn.r5375)
;
_cell_angle_alpha                74.817(5)
_cell_angle_beta                 76.036(5)
_cell_angle_gamma                83.497(5)
_cell_formula_units_Z            4
_cell_length_a                   10.3724(6)
_cell_length_b                   14.9192(9)
_cell_length_c                   20.5335(12)
_cell_measurement_reflns_used    3005
_cell_measurement_temperature    298
_cell_measurement_theta_max      29.0680
_cell_measurement_theta_min      2.7630
_cell_volume                     2971.7(3)
_computing_cell_refinement       'CrysAlisPro 1.171.39.7f (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.39.7f (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.39.7f (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    'ShelXD (Sheldrick, 2008)'
_diffrn_ambient_temperature      298
_diffrn_detector                 'CCD plate'
_diffrn_measured_fraction_theta_full 0.896
_diffrn_measured_fraction_theta_max 0.896
_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     19.00 119.50   0.30   20.00    --   29.89  54.00 -60.00  335
  2  \w     87.00 114.00   0.30   20.00    --   29.89  54.00-180.00   90
  3  \w      8.00  32.90   0.30   20.00    --   29.89  54.00-180.00   83
  4  \w    -15.00  12.00   0.30   20.00    --   29.89  54.00-120.00   90
  5  \w    -69.00 115.20   0.30   20.00    --   29.89  54.00  60.00  614
  6  \w    -69.00 -43.20   0.30   20.00    --   29.89  54.00-180.00   86
  7  \w    -66.00 -41.10   0.30   20.00    --   29.89  54.00 -60.00   83
;
_diffrn_measurement_device       'two-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB Mini (ROW)'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0688185000
_diffrn_orient_matrix_UB_12      -0.0120809000
_diffrn_orient_matrix_UB_13      -0.0023593000
_diffrn_orient_matrix_UB_21      0.0022915000
_diffrn_orient_matrix_UB_22      0.0298594000
_diffrn_orient_matrix_UB_23      0.0214447000
_diffrn_orient_matrix_UB_31      -0.0154401000
_diffrn_orient_matrix_UB_32      -0.0373658000
_diffrn_orient_matrix_UB_33      0.0296868000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0346
_diffrn_reflns_av_unetI/netI     0.0855
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       20
_diffrn_reflns_limit_k_min       -22
_diffrn_reflns_limit_l_max       30
_diffrn_reflns_limit_l_min       -30
_diffrn_reflns_number            30505
_diffrn_reflns_theta_full        32.78
_diffrn_reflns_theta_max         32.78
_diffrn_reflns_theta_min         2.63
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_source_type              'Enhance (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    0.067
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.55319
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.39.7f (Rigaku Oxford Diffraction, 2015)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            'clear light colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.144
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             1096
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.15
_refine_diff_density_max         0.357
_refine_diff_density_min         -0.234
_refine_diff_density_rms         0.048
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.994
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     717
_refine_ls_number_reflns         19717
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.994
_refine_ls_R_factor_all          0.1905
_refine_ls_R_factor_gt           0.0854
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.1215P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2055
_refine_ls_wR_factor_ref         0.2920
_reflns_number_gt                7641
_reflns_number_total             19717
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jo8b00607_si_002.cif
_cod_data_source_block           10a
_cod_database_code               4035555
_chemical_oxdiff_formula         'c37 H37 N O'
_reflns_odcompleteness_completeness 99.89
_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 N(H) groups
 At 1.5 times of:
  All C(H,H,H) groups, All O(H) groups
2.a Ternary CH refined with riding coordinates:
 C004(H004), C022(H022)
2.b Aromatic/amide H refined with riding coordinates:
 C001(H001), C013(H013), N014(H014), C017(H017), C019(H019), N023(H023),
 C029(H029), C033(H033), C036(H036), C039(H039), C040(H040), C042(H042),
 C043(H043), C044(H044), C045(H045), C047(H047), C048(H048), C049(H049),
 C051(H051), C052(H052), C054(H054), C055(H055), C056(H056), C057(H057),
 C059(H059), C060(H060), C063(H063), C064(H064), C068(H068), C070(H070),
 C072(H072), C075(H075), C077(H077), C078(H078)
2.c Idealised Me refined as rotating group:
 C053(H05A,H05B,H05C), C058(H05D,H05E,H05F), C061(H06J,H06K,H06L), C062(H06A,
 H06B,H06C), C065(H06D,H06E,H06F), C066(H06G,H06H,H06I), C067(H06M,H06N,H06O),
 C069(H06P,H06Q,H06R), C071(H07A,H07B,H07C), C073(H07D,H07E,H07F), C074(H07G,
 H07H,H07I), C076(H07J,H07K,H07L)
2.d Idealised tetrahedral OH refined as rotating group:
 O002(H002), O035(H035)
;
_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 1.472
_oxdiff_exptl_absorpt_empirical_full_min 0.681