Divergent Gold-catalyzed Reactions of Cyclopropenylmethyl Sulfonamides with Tethered Heteroaromatics
Drew, Melanie; Arndt, Sebastian; Richardson, Christopher; Rudolph, Matthias; Hashmi, Stephen; Hyland, Christopher James Timothy; Chemical Communications  (2019) –; doi:10.1039/C9CC06241F

data_7124323
_publ_section_title
;
 Divergent Gold-catalyzed Reactions of Cyclopropenylmethyl Sulfonamides
 with Tethered Heteroaromatics
;
_journal_name_full               'Chemical Communications'
_journal_paper_doi               10.1039/C9CC06241F
_journal_year                    2019
_chemical_formula_moiety         'C27 H34 N2 O2 S'
_chemical_formula_sum            'C27 H34 N2 O2 S'
_chemical_formula_weight         450.62
_chemical_name_systematic
(E)-9-methyl-4-(oct-4-en-4-yl)-2-tosyl-2,3,4,9-tetrahydro-1H-pyrido[3,4-b]indole
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   geom
_audit_creation_date             2019-04-08
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_audit_update_record
;
2019-04-11 deposited with the CCDC.    2019-10-14 downloaded from the CCDC.
;
_cell_angle_alpha                71.699(5)
_cell_angle_beta                 75.057(5)
_cell_angle_gamma                78.424(4)
_cell_formula_units_Z            2
_cell_length_a                   7.9109(4)
_cell_length_b                   13.3891(6)
_cell_length_c                   14.4067(9)
_cell_measurement_reflns_used    5857
_cell_measurement_temperature    149.99(10)
_cell_measurement_theta_max      29.7530
_cell_measurement_theta_min      2.7940
_cell_volume                     1387.81(14)
_computing_cell_refinement       'CrysAlisPro 1.171.39.46 (Rigaku OD, 2018)'
_computing_data_collection       'CrysAlisPro 1.171.39.46 (Rigaku OD, 2018)'
_computing_data_reduction        'CrysAlisPro 1.171.39.46 (Rigaku OD, 2018)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      149.99(10)
_diffrn_detector                 'HyPix Bantam HPC'
_diffrn_measured_fraction_theta_full 0.980
_diffrn_measured_fraction_theta_max 0.933
_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    -22.00  47.00   0.50   30.00    --   20.00  54.00 150.00  138
  2  \w     74.00 100.00   0.50   30.00    --   20.00  54.00 150.00   52
  3  \w    -73.00 -45.00   0.50   30.00    --   20.00  54.00   0.00   56
  4  \w    -36.00  64.50   0.50   30.00    --   20.00  54.00   0.00  201
  5  \w     76.00 110.00   0.50   30.00    --   20.00  54.00   0.00   68
  6  \w    -10.00 108.00   0.50   30.00    --   20.00  54.00 -90.00  236
  7  \w    -73.00  63.00   0.50   30.00    --   20.00  54.00  60.00  272
  8  \w     73.00 109.00   0.50   30.00    --   20.00  54.00  60.00   72
  9  \w    -74.00 110.00   0.50   30.00    --   20.00  54.00 -60.00  368
 10  \w    -74.00 -48.00   0.50   30.00    --   20.00  54.00-150.00   52
 11  \w     11.00  38.00   0.50   30.00    --   20.00  54.00-150.00   54
 12  \w     72.00 108.00   0.50   30.00    --   20.00  54.00-150.00   72
 13  \w     40.00  65.00   0.50   30.00    --   20.00  54.00  30.00   50
 14  \w     81.00 106.00   0.50   30.00    --   20.00  54.00  30.00   50
 15  \w    -64.00 -37.00   0.50   30.00    --   20.00  54.00-120.00   54
 16  \w    -69.00 -40.00   0.50   30.00    --   20.00  54.00  90.00   58
 17  \w     33.00  58.00   0.50   30.00    --   20.00  54.00  90.00   50
 18  \w    -70.00 -43.00   0.50   30.00    --   20.00  54.00 150.00   54
;
_diffrn_measurement_device       'two-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB Mini II'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0060097000
_diffrn_orient_matrix_UB_12      0.0546807000
_diffrn_orient_matrix_UB_13      -0.0263355000
_diffrn_orient_matrix_UB_21      0.0210969000
_diffrn_orient_matrix_UB_22      -0.0132910000
_diffrn_orient_matrix_UB_23      -0.0459639000
_diffrn_orient_matrix_UB_31      -0.0909928000
_diffrn_orient_matrix_UB_32      0.0008615000
_diffrn_orient_matrix_UB_33      0.0025108000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0298
_diffrn_reflns_av_unetI/netI     0.0449
_diffrn_reflns_Laue_measured_fraction_full 0.980
_diffrn_reflns_Laue_measured_fraction_max 0.933
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_k_min       -19
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            24667
_diffrn_reflns_point_group_measured_fraction_full 0.980
_diffrn_reflns_point_group_measured_fraction_max 0.933
_diffrn_reflns_theta_full        29.000
_diffrn_reflns_theta_max         30.786
_diffrn_reflns_theta_min         1.888
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_source_type              'Rigaku (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    0.139
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.93042
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.39.46 (Rigaku Oxford Diffraction, 2018)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            'clear colourless'
_exptl_crystal_density_diffrn    1.078
_exptl_crystal_description       plate
_exptl_crystal_F_000             484
_exptl_crystal_recrystallization_method 'crystallised from hexane'
_exptl_crystal_size_max          0.5
_exptl_crystal_size_mid          0.18
_exptl_crystal_size_min          0.06
_refine_diff_density_max         0.278
_refine_diff_density_min         -0.300
_refine_diff_density_rms         0.055
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.058
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     297
_refine_ls_number_reflns         8123
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.058
_refine_ls_R_factor_all          0.0691
_refine_ls_R_factor_gt           0.0482
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0722P)^2^+0.0991P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1275
_refine_ls_wR_factor_ref         0.1366
_reflns_Friedel_coverage         0.000
_reflns_number_gt                5971
_reflns_number_total             8123
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c9cc06241f2.cif
_cod_data_source_block           exp_109_md2
_cod_original_cell_volume        1387.82(14)
_cod_database_code               7124323
_chemical_oxdiff_formula         'C27 H34 N2 O2 S'
_chemical_oxdiff_usercomment     'Melanie Drew'
_shelx_estimated_absorpt_t_max   0.992
_shelx_estimated_absorpt_t_min   0.934
_reflns_odcompleteness_completeness 99.21
_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. Others
 Sof(H9MD)=Sof(H9ME)=Sof(H9MF)=1-FVAR(1)
 Sof(H9MA)=Sof(H9MB)=Sof(H9MC)=FVAR(1)
3.a Ternary CH refined with riding coordinates:
 C4(H4)
3.b Secondary CH2 refined with riding coordinates:
 C1(H1A,H1B), C3(H3A,H3B), C2O(H2OA,H2OB), C3O(H3OA,H3OB), C6O(H6OA,H6OB),
 C7O(H7OA,H7OB)
3.c Aromatic/amide H refined with riding coordinates:
 C5(H5), C6(H6), C7(H7), C8(H8), C5O(H5O), C2T(H2T), C3T(H3T), C5T(H5T),
 C6T(H6T)
3.d Idealised Me refined as rotating group:
 C9ME(H9MA,H9MB,H9MC), C9ME(H9MD,H9ME,H9MF), C1O(H1OA,H1OB,H1OC), C8O(H8OA,
 H8OB,H8OC), C4ME(H4MA,H4MB,H4MC)
;
_shelx_res_checksum              64773
_shelx_fab_checksum              28745
_olex2_exptl_crystal_mounting_method 'Mitegen mount + Paratone'
_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 1.113
_oxdiff_exptl_absorpt_empirical_full_min 0.929