Rhodium catalyzed cycloisomerization and tandem Diels-Alder reaction for facile access to diverse bicyclic and tricyclic heterocycles
Breit, Bernhard; Zhou, Yirong; Nikbakht, Ali -; Bauer, Felix; Chemical Science  (2019) –; doi:10.1039/C9SC00980A

data_1550834
_publ_section_title
;
 Rhodium catalyzed cycloisomerization and tandem Diels-Alder reaction for
 facile access to diverse bicyclic and tricyclic heterocycles
;
_journal_name_full               'Chemical Science'
_journal_paper_doi               10.1039/C9SC00980A
_journal_year                    2019
_chemical_formula_moiety         'C14 H17 N O2 S'
_chemical_formula_sum            'C14 H17 N O2 S'
_chemical_formula_weight         263.34
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2ybc'
_space_group_name_H-M_alt        'P 1 21/c 1'
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 1 21/c 1'
_atom_sites_solution_hydrogens   geom
_audit_creation_date             2017-10-10
_audit_creation_method
;
Olex2 1.2
(compiled 2017.08.10 svn.r3458 for OlexSys, GUI svn.r5381)
;
_audit_update_record
;
2017-10-10 deposited with the CCDC.    2019-04-02 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 95.237(4)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   6.0835(5)
_cell_length_b                   9.3137(7)
_cell_length_c                   22.9507(17)
_cell_measurement_reflns_used    9932
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      27.53
_cell_measurement_theta_min      2.36
_cell_volume                     1294.96(17)
_computing_cell_refinement       'SAINT V8.38A (Madison, 2016)'
_computing_data_collection       'Bruker APEXII'
_computing_data_reduction        'SAINT V8.38A (Madison, 2016)'
_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 2014/5 (Sheldrick, 2014)'
_diffrn_ambient_temperature      100.0
_diffrn_detector_area_resol_mean 8
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type  'Bruker SMART APEX CCD area detector'
_diffrn_measurement_method       '\w and \f scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0295
_diffrn_reflns_av_unetI/netI     0.0173
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       29
_diffrn_reflns_limit_l_min       -29
_diffrn_reflns_number            21906
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.562
_diffrn_reflns_theta_min         1.782
_diffrn_source                   'sealed tube'
_diffrn_source_current           50
_diffrn_source_voltage           0.6
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.243
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_correction_T_min  0.7004
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
'SADABS-2016/2 (Bruker,2016/2) was used for absorption correction. wR2(int) was 0.1510 before and 0.0435 after correction. The Ratio of minimum to maximum transmission is 0.9394. The \l/2 correction factor is Not present.'
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.351
_exptl_crystal_description       needle
_exptl_crystal_F_000             560
_exptl_crystal_recrystallization_method
'The material was recrystallised from a mixture of ethyl acetate and n-pentane by waiting'
_exptl_crystal_size_max          0.36
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.1
_refine_diff_density_max         0.397
_refine_diff_density_min         -0.407
_refine_diff_density_rms         0.049
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.081
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     164
_refine_ls_number_reflns         2987
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.081
_refine_ls_R_factor_all          0.0329
_refine_ls_R_factor_gt           0.0308
_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^)+(0.0314P)^2^+0.8707P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0800
_refine_ls_wR_factor_ref         0.0814
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2789
_reflns_number_total             2987
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c9sc00980a2.cif
_cod_data_source_block           breit_zyr_2_a
_cod_database_code               1550834
_shelx_shelxl_version_number     2017/1
_shelx_estimated_absorpt_t_max   0.976
_shelx_estimated_absorpt_t_min   0.917
_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.a Secondary CH2 refined with riding coordinates:
 C1(H1A,H1B), C4(H4A,H4B), C5(H5A,H5B)
2.b Aromatic/amide H refined with riding coordinates:
 C9(H9), C10(H10), C12(H12), C13(H13)
2.c X=CH2 refined with riding coordinates:
 C6(H6A,H6B), C7(H7A,H7B)
2.d Idealised Me refined as rotating group:
 C14(H14A,H14B,H14C)
;
_shelx_res_checksum              97649
_olex2_diffrn_ambient_temperature_device 'Oxford Cryosystems 800'
_olex2_exptl_crystal_mounting_method
'The crystal was mounted on a MITIGEN holder in perfluoroether oil'
_olex2_submission_special_instructions 'No special instructions were received'