1,2-Addition versus homoconjugate addition reactions of indoles and electron-rich arenes to α-cyclopropyl N-acyliminium ions: synthetic and computational studies.
Ryder, Greg M.; Wille, Uta; Willis, Anthony C.; Pyne, Stephen G.; Organic & biomolecular chemistry 17 (2019) 7025–7035; doi:10.1039/c9ob01363f

data_7156953
_publ_section_title
;
 1,2-Addition versus homoconjugate addition reactions of indoles and
 electron-rich arenes to \a-cyclopropyl N-acyliminium ions: synthetic and
 computational studies.
;
_journal_issue                   29
_journal_name_full               'Organic &amp; biomolecular chemistry'
_journal_page_first              7025
_journal_page_last               7035
_journal_paper_doi               10.1039/c9ob01363f
_journal_volume                  17
_journal_year                    2019
_chemical_absolute_configuration ad
_chemical_compound_source        ' from U of Wollongong '
_chemical_formula_moiety         'C23 H24 N2 O2'
_chemical_formula_sum            'C23 H24 N2 O2'
_chemical_formula_weight         360.46
_space_group_IT_number           4
_space_group_name_Hall           'P 2yb'
_space_group_name_H-M_alt        'P 1 21 1'
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  'P 2yb'
_symmetry_space_group_name_H-M   'P 1 21 1'
_atom_sites_solution_hydrogens   difmap
_atom_sites_solution_primary     direct
_audit_creation_date             16-03-15
_audit_creation_method           CRYSTALS_ver_14.40
_audit_update_record
;
2019-06-10 deposited with the CCDC.    2019-07-03 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 92.3726(8)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   7.3603(1)
_cell_length_b                   16.0890(2)
_cell_length_c                   16.5566(2)
_cell_measurement_reflns_used    18719
_cell_measurement_temperature    150
_cell_measurement_theta_max      72
_cell_measurement_theta_min      3
_cell_volume                     1958.95(4)
_computing_cell_refinement       'CrysAlisPro (Agilent Technologies, 2015)'
_computing_data_collection
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35h (release 09-02-2015 CrysAlis171 .NET)
(compiled Feb 9 2015,16:26:32)
;
_computing_data_reduction        'CrysAlisPro (Agilent Technologies, 2015)'
_computing_molecular_graphics    'PLATON (Spek, 2008)'
_computing_publication_material  'CRYSTALS (Betteridge et al., 2003)'
_computing_structure_refinement  'CRYSTALS (Betteridge et al., 2003)'
_computing_structure_solution    'SIR92 (Altomare et al., 1994)'
_diffrn_ambient_temperature      150
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device       Area
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, EosS2'
_diffrn_measurement_method       \w
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_source         'Supernova (Cu) X-ray Source'
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.034
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       19
_diffrn_reflns_limit_k_min       -19
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            30309
_diffrn_reflns_theta_full        72.389
_diffrn_reflns_theta_max         72.389
_diffrn_reflns_theta_min         3.833
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.620
_exptl_absorpt_correction_T_max  0.96
_exptl_absorpt_correction_T_min  0.93
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35h (release 09-02-2015 CrysAlis171 .NET)
(compiled Feb 9 2015,16:26:32)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            'pale brown'
_exptl_crystal_density_diffrn    1.222
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             768
_exptl_crystal_size_max          0.233
_exptl_crystal_size_mid          0.075
_exptl_crystal_size_min          0.073
_refine_diff_density_max         0.12
_refine_diff_density_min         -0.14
_refine_ls_abs_structure_details 'Flack (1983), 3571 Friedel-pairs'
_refine_ls_abs_structure_Flack   0.05(12)
_refine_ls_extinction_method     None
_refine_ls_goodness_of_fit_ref   1.0042
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     501
_refine_ls_number_reflns         7576
_refine_ls_number_restraints     23
_refine_ls_R_factor_all          0.0324
_refine_ls_R_factor_gt           0.0316
_refine_ls_shift/su_max          0.0081346
_refine_ls_shift/su_mean         0.0002778
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
;
 Method= Modified Sheldrick 
 w=1/[\s^2^(F^2^) + ( 0.04P)^2^ + 0.26P] 
 ,where P=(max(Fo^2^,0) + 2Fc^2^)/3 
;
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_all         0.0820
_refine_ls_wR_factor_gt          0.0811
_refine_ls_wR_factor_ref         0.0820
_reflns_limit_h_max              9
_reflns_limit_h_min              -9
_reflns_limit_k_max              19
_reflns_limit_k_min              -19
_reflns_limit_l_max              20
_reflns_limit_l_min              0
_reflns_number_gt                7384
_reflns_number_total             7576
_reflns_threshold_expression     I>2.0\s(I)
_oxford_diffrn_Wilson_B_factor   3.13
_oxford_diffrn_Wilson_scale      0.01
_oxford_refine_ls_r_factor_ref   0.0324
_oxford_refine_ls_scale          8.15(14)
_oxford_reflns_number_all        7576
_oxford_reflns_threshold_expression_ref I>-10.0\s(I)
_oxford_structure_analysis_title
'Z:\pyn1604SN\Tony_pyn1604CSN_dat At 11:15 on'
_cod_data_source_file            c9ob01363f3.cif
_cod_data_source_block           pyn1604SN
_cod_depositor_comments          'Adding full bibliography for 7156953.cif.'
_cod_original_sg_symbol_H-M      'P 1 21 1 '
_cod_database_code               7156953
_iucr_refine_instruction_details_constraints
;
BLOCK SCALE X'S, O(1,U'S) UNTIL C(73) 
CONT C(55,OCC) UNTIL C(57) C(51,OCC) 
CONT C(151,OCC,U[ISO]) UNTIL C(157) 
CONT ENANTIO 
EQUIV C(55,OCC) UNTIL C(57) C(51,OCC) C(151,OCC) UNTIL C(157) 
WEIGHT -1   C(151,OCC) UNTIL C(157) 
FIX C(151,U[ISO]) UNTIL C(157) 
RIDE N   (   2,X'S) H   (   1,X'S) 
RIDE N   (  52,X'S) H   (   2,X'S) 
RIDE C   (   2,X'S) H   (  21,X'S) 
RIDE C   (   3,X'S) H   (  31,X'S) H   (  32,X'S) 
RIDE C   (   5,X'S) H   (  51,X'S) 
RIDE C   (   6,X'S) H   (  61,X'S) H   (  62,X'S) 
RIDE C   (   7,X'S) H   (  71,X'S) H   (  72,X'S) 
RIDE C   (  10,X'S) H   ( 101,X'S) 
RIDE C   (  11,X'S) H   ( 111,X'S) 
RIDE C   (  12,X'S) H   ( 121,X'S) 
RIDE C   (  13,X'S) H   ( 131,X'S) 
RIDE C   (  15,X'S) H   ( 151,X'S) 
RIDE C   (  16,X'S) H   ( 161,X'S) H   ( 162,X'S) 
RIDE C   (  18,X'S) H   ( 181,X'S) 
RIDE C   (  19,X'S) H   ( 191,X'S) 
RIDE C   (  20,X'S) H   ( 201,X'S) 
RIDE C   (  21,X'S) H   ( 211,X'S) 
RIDE C   (  22,X'S) H   ( 221,X'S) 
RIDE C   (  23,X'S) H   ( 231,X'S) H   ( 232,X'S) H   ( 233,X'S) 
RIDE C   (  52,X'S) H   ( 521,X'S) 
RIDE C   (  53,X'S) H   ( 531,X'S) H   ( 532,X'S) 
RIDE C   (  55,X'S) H   ( 551,X'S) 
RIDE C(56,X'S) H(561,X'S) H(562,X'S) 
RIDE C   (  57,X'S) H(571,X'S) H(572,X'S) 
RIDE C   (  60,X'S) H   ( 601,X'S) 
RIDE C   (  61,X'S) H   ( 611,X'S) 
RIDE C   (  62,X'S) H   ( 621,X'S) 
RIDE C   (  63,X'S) H   ( 631,X'S) 
RIDE C   (  65,X'S) H   ( 651,X'S) 
RIDE C   (  66,X'S) H   ( 661,X'S) H   ( 662,X'S) 
RIDE C   (  68,X'S) H   ( 681,X'S) 
RIDE C   (  69,X'S) H   ( 691,X'S) 
RIDE C   (  70,X'S) H   ( 701,X'S) 
RIDE C   (  71,X'S) H   ( 711,X'S) 
RIDE C   (  72,X'S) H   ( 721,X'S) 
RIDE C   (  73,X'S) H   ( 731,X'S) H   ( 732,X'S) H   ( 733,X'S) 
RIDE C   (  155,X'S) H   ( 1551,X'S) 
RIDE C(156,X'S)  H(1561,X'S) H(1562,X'S) 
RIDE C   (  157,X'S) H(1571,X'S) H(1572,X'S) 
END                                                                             
;
_iucr_refine_instruction_details_restraints
;
DIST 1.52, .01 = C(51) TO C(55) 
DIST 1.52, .01 =  C(151) TO C(155) 
DIST 1.51, .01 = C(55) TO C(56), C(155) TO C(156) 
DIST 1.51, .01 = C(55) TO C(57), C(155) TO C(157) 
DIST 1.51, .01 = C(56) TO C(57), C(156) TO C(157) 
ANGLE 124, 2 = C(51) TO C(55) TO C(56), C(51) TO C(155) TO C(56) 
ANGLE 124, 2 = C(51) TO C(55) TO C(57), C(51) TO C(155) TO C(157) 
REM ANGLE 60, 2 = C(56) TO C(55) TO C(57), C(56) TO C(155) TO C(157) 
REM 
DIST 1.49, .01 = C(151) TO N(51) 
DIST 1.57, .01 = C(151) TO C(52) 
DIST 1.51, .01 = C(151) TO C(58) 
DIST 1.52, .01 = C(151) TO C(155) 
ANGLE 101, 2 = N(51) TO C(151) TO C(52) 
ANGLE 109, 2 = N(51) TO C(151) TO C(58) 
ANGLE 109, 2 = N(51) TO C(151) TO C(155) 
ANGLE 113, 2 = C(52) TO C(151) TO C(58) 
ANGLE 113, 2 = C(52) TO C(151) TO C(155) 
ANGLE 110, 2 = C(58) TO C(151) TO C(155) 
NO 
REM   HREST   START (DO NOT REMOVE THIS LINE) 
REM   HREST   END (DO NOT REMOVE THIS LINE) 
END                                                                             
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