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_7124322
_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         'C24 H33 N O3 S'
_chemical_formula_sum            'C24 H33 N O3 S'
_chemical_formula_weight         415.57
_chemical_name_systematic
7,8-dipropyl-2-tosyl-2,3,6,8a-tetrahydro-1H-3a,6-epoxycyclohepta[c]pyrrole
_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             2019-04-11
_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                96.427(5)
_cell_angle_beta                 101.078(5)
_cell_angle_gamma                109.297(6)
_cell_formula_units_Z            4
_cell_length_a                   11.7737(8)
_cell_length_b                   11.7820(8)
_cell_length_c                   17.9734(8)
_cell_measurement_reflns_used    4800
_cell_measurement_temperature    150.00(10)
_cell_measurement_theta_max      24.8800
_cell_measurement_theta_min      1.9570
_cell_volume                     2267.5(3)
_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      150.00(10)
_diffrn_detector                 'HyPix Bantam HPC'
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.938
_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    -37.00  95.00   0.50   50.00    --   20.00  54.00 150.00  264
  2  \w    -70.00 -38.00   0.50   50.00    --   20.00  54.00  30.00   64
  3  \w    -30.00  11.00   0.50   50.00    --   20.00  54.00  30.00   82
  4  \w     14.00  83.00   0.50   50.00    --   20.00  54.00  30.00  138
  5  \w    -73.00  19.00   0.50   50.00    --   20.00  54.00 -90.00  184
  6  \w     22.00  48.00   0.50   50.00    --   20.00  54.00 -90.00   52
  7  \w     56.00 107.00   0.50   50.00    --   20.00  54.00 -90.00  102
  8  \w    -72.00 -47.00   0.50   50.00    --   20.00  54.00 -30.00   50
  9  \w     -8.00  17.00   0.50   50.00    --   20.00  54.00 -30.00   50
 10  \w     50.00  75.00   0.50   50.00    --   20.00  54.00 -30.00   50
 11  \w    -70.00  92.50   0.50   50.00    --   20.00  54.00  90.00  325
 12  \w    -70.00 -25.00   0.50   50.00    --   20.00  54.00-180.00   90
 13  \w      1.00  39.00   0.50   50.00    --   20.00  54.00-180.00   76
 14  \w     85.00 110.00   0.50   50.00    --   20.00  54.00-180.00   50
 15  \w    -69.00  44.00   0.50   50.00    --   20.00  54.00-150.00  226
 16  \w    -42.00 -17.00   0.50   50.00    --   20.00  54.00 -60.00   50
 17  \w    -48.00 -23.00   0.50   50.00    --   20.00  54.00   0.00   50
 18  \w     48.00  73.00   0.50   50.00    --   20.00  54.00   0.00   50
 19  \w    -68.00 -35.00   0.50   50.00    --   20.00  54.00 120.00   66
 20  \w    -68.00 -43.50   0.50   50.00    --   20.00  54.00 150.00   49
;
_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      -0.0091499000
_diffrn_orient_matrix_UB_12      -0.0216525000
_diffrn_orient_matrix_UB_13      -0.0399395000
_diffrn_orient_matrix_UB_21      -0.0195797000
_diffrn_orient_matrix_UB_22      0.0488037000
_diffrn_orient_matrix_UB_23      -0.0088554000
_diffrn_orient_matrix_UB_31      0.0621759000
_diffrn_orient_matrix_UB_32      0.0370048000
_diffrn_orient_matrix_UB_33      0.0019273000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0686
_diffrn_reflns_av_unetI/netI     0.1120
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.938
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_l_max       25
_diffrn_reflns_limit_l_min       -25
_diffrn_reflns_number            41897
_diffrn_reflns_point_group_measured_fraction_full 0.996
_diffrn_reflns_point_group_measured_fraction_max 0.938
_diffrn_reflns_theta_full        22.500
_diffrn_reflns_theta_max         30.683
_diffrn_reflns_theta_min         1.890
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_source_type              'Rigaku (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    0.167
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.72297
_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_colour_lustre     clear
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.217
_exptl_crystal_description       plate
_exptl_crystal_F_000             896
_exptl_crystal_recrystallization_method
'Re-crystallisation from solvent: pentane'
_exptl_crystal_size_max          0.68
_exptl_crystal_size_mid          0.05
_exptl_crystal_size_min          0.02
_refine_diff_density_max         0.468
_refine_diff_density_min         -0.374
_refine_diff_density_rms         0.061
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.045
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     549
_refine_ls_number_reflns         13180
_refine_ls_number_restraints     5
_refine_ls_restrained_S_all      1.045
_refine_ls_R_factor_all          0.1465
_refine_ls_R_factor_gt           0.0796
_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^)+(0.0579P)^2^+0.5640P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1393
_refine_ls_wR_factor_ref         0.1597
_reflns_Friedel_coverage         0.000
_reflns_number_gt                7923
_reflns_number_total             13180
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c9cc06241f2.cif
_cod_data_source_block           exp_86-2md1
_cod_database_code               7124322
_shelx_shelxl_version_number     2017/1
_chemical_oxdiff_formula         'C24H33 N O3 S'
_chemical_oxdiff_usercomment     b10e355_pure
_shelx_estimated_absorpt_t_max   0.997
_shelx_estimated_absorpt_t_min   0.895
_reflns_odcompleteness_completeness 99.26
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     24.97
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All C(H,H,H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2. Restrained distances
 C72B-C73B \\sim C72B-C100
 with sigma of 0.02
 C73B-C74B \\sim C100-C101
 with sigma of 0.02
3. Rigid body (RIGU) restrains
 C100, C101
 with sigma for 1-2 distances of 0.004 and sigma for 1-3 distances of 0.004
4. Others
 Sof(H72C)=Sof(H72D)=Sof(C101)=Sof(H10A)=Sof(H10B)=Sof(H10C)=Sof(C100)=
 Sof(H10D)=Sof(H10E)=1-FVAR(1)
 Sof(H72A)=Sof(H72B)=Sof(C73B)=Sof(H73A)=Sof(H73B)=Sof(C74B)=Sof(H74A)=
 Sof(H74B)=Sof(H74C)=FVAR(1)
5.a Ternary CH refined with riding coordinates:
 C6(H6), C8A(H8A), C6B(H6B), C8AB(H8AB)
5.b Secondary CH2 refined with riding coordinates:
 C1(H1A,H1B), C3(H3A,H3B), C71(H71C,H71D), C72(H72E,H72F), C73(H73C,H73D),
 C81(H81C,H81D), C82(H82C,H82D), C83(H83C,H83D), C1B(H1BA,H1BB), C3B(H3BA,H3BB),
  C71B(H71A,H71B), C72B(H72A,H72B), C72B(H72C,H72D), C73B(H73A,H73B), C81B(H81A,
 H81B), C82B(H82A,H82B), C83B(H83A,H83B), C100(H10D,H10E)
5.c Aromatic/amide H refined with riding coordinates:
 C2T(H2T), C3T(H3T), C4(H4), C5(H5), C5T(H5T), C6T(H6T), C2TB(H2TB),
 C3TB(H3TB), C4B(H4B), C5B(H5B), C5TB(H5TB), C6TB(H6TB)
5.d Idealised Me refined as rotating group:
 C7T(H7TD,H7TE,H7TF), C74(H74D,H74E,H74F), C84(H84D,H84E,H84F), C7TB(H7TA,H7TB,
 H7TC), C74B(H74A,H74B,H74C), C84B(H84A,H84B,H84C), C101(H10A,H10B,H10C)
;
_shelx_res_checksum              47597
_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 1.321
_oxdiff_exptl_absorpt_empirical_full_min 0.849