Direct Access to Bridged Tetrahydroquinolines and Chromanes via an InCl<sub>3</sub>-Catalyzed Sequential Three-Component Cascade.
Vachan, B. S.; Karuppasamy, Muthu; Jan, Gowsia; Bhuvanesh, Nattamai; Maheswari, C. Uma; Sridharan, Vellaisamy; The Journal of organic chemistry  (2020) –; doi:10.1021/acs.joc.0c00893

data_4038460
_publ_section_title
;
 Direct Access to Bridged Tetrahydroquinolines and Chromanes via an
 InCl<sub>3</sub>-Catalyzed Sequential Three-Component Cascade.
;
_journal_name_full               'The Journal of organic chemistry'
_journal_paper_doi               10.1021/acs.joc.0c00893
_journal_year                    2020
_chemical_formula_moiety         'C28 H27 Br N2 O4 S'
_chemical_formula_sum            'C28 H27 Br N2 O4 S'
_chemical_formula_weight         567.48
_space_group_crystal_system      monoclinic
_space_group_IT_number           15
_space_group_name_Hall           '-C 2yc'
_space_group_name_H-M_alt        'C 1 2/c 1'
_atom_sites_solution_hydrogens   geom
_audit_creation_date             2019-09-19
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_cell_angle_alpha                90
_cell_angle_beta                 120.8473(12)
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   28.8676(12)
_cell_length_b                   10.9791(5)
_cell_length_c                   18.9515(10)
_cell_measurement_reflns_used    9900
_cell_measurement_temperature    110.0
_cell_measurement_theta_max      25.020
_cell_measurement_theta_min      2.179
_cell_volume                     5156.8(4)
_computing_cell_refinement
'SAINT V8.38 Bruker AXS Inc., Madison, WI, USA.'
_computing_data_reduction
'SAINT V8.38 Bruker AXS Inc., Madison, WI, USA.'
_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 2018/2 (Sheldrick, 2018)'
_diffrn_ambient_temperature      110.0
_diffrn_measured_fraction_theta_full 0.995
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0398
_diffrn_reflns_av_unetI/netI     0.0590
_diffrn_reflns_Laue_measured_fraction_full 0.995
_diffrn_reflns_Laue_measured_fraction_max 0.995
_diffrn_reflns_limit_h_max       34
_diffrn_reflns_limit_h_min       -25
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_number            10285
_diffrn_reflns_point_group_measured_fraction_full 0.995
_diffrn_reflns_point_group_measured_fraction_max 0.995
_diffrn_reflns_theta_full        24.996
_diffrn_reflns_theta_max         24.996
_diffrn_reflns_theta_min         2.504
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    1.713
_exptl_absorpt_correction_T_max  0.3309
_exptl_absorpt_correction_T_min  0.1198
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
'SADABS-2016/2 (Bruker,2016/2) was used for absorption correction. wR2(int) was 0.1263 before and 0.0632 after correction. The Ratio of minimum to maximum transmission is 0.3620. The \l/2 correction factor is Not present.'
_exptl_crystal_colour            yellow
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.462
_exptl_crystal_description       block
_exptl_crystal_F_000             2336
_exptl_crystal_size_max          0.412
_exptl_crystal_size_mid          0.358
_exptl_crystal_size_min          0.243
_refine_diff_density_max         0.431
_refine_diff_density_min         -0.711
_refine_diff_density_rms         0.066
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.021
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     387
_refine_ls_number_reflns         4511
_refine_ls_number_restraints     311
_refine_ls_restrained_S_all      0.998
_refine_ls_R_factor_all          0.0692
_refine_ls_R_factor_gt           0.0448
_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^)+(0.0488P)^2^+6.1654P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0988
_refine_ls_wR_factor_ref         0.1122
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3346
_reflns_number_total             4511
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            jo0c00893_si_002.cif
_cod_data_source_block           vbs2n
_cod_database_code               4038460
_shelx_shelxl_version_number     2018/3
_shelx_estimated_absorpt_t_max   0.681
_shelx_estimated_absorpt_t_min   0.539
_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. Restrained distances
 O4-C20 \\sim O4A-C20A
 with sigma of 0.02
 O4-C19 \\sim O4A-C19
 with sigma of 0.02
 C19-C20 \\sim C20-C20A
 with sigma of 0.02
3. Uiso/Uaniso restraints and constraints
Br1 \\sim C1 \\sim C2 \\sim C8 \\sim C9 \\sim C10 \\sim C11 \\sim Br1A \\sim
C1A \\sim C2A \\sim C8A \\sim C9A \\sim C10A \\sim C11A: within 2A with sigma
of 0.02 and sigma for terminal atoms of 0.04
Uanis(O4) = Uanis(O4A)
Uanis(C20) = Uanis(C20A)
Uanis(C1A) = Uanis(C1)
Uanis(C2) = Uanis(C2A)
4. Rigid body (RIGU) restrains
 Br1, C1, C2, C8, C9, C10, C11, Br1A, C1A, C2A, C8A, C9A, C10A, C11A
 with sigma for 1-2 distances of 0.02 and sigma for 1-3 distances of 0.02
5. Same fragment restrains
{Br1, C1, C2, C8, C9, C10, C11} sigma for 1-2: 0.02, 1-3: 0.04
as
{Br1A, C1A, C2A, C8A, C9A, C10A, C11A}
6. Others
 Sof(H3B)=Sof(Br1A)=Sof(C1A)=Sof(C2A)=Sof(C8A)=Sof(H8A)=Sof(C9A)=Sof(H9A)=
 Sof(C10A)=Sof(C11A)=Sof(H11A)=Sof(O4A)=Sof(C20A)=Sof(H20D)=Sof(H20E)=Sof(H20F)=
 1-FVAR(1)
 Sof(H3A)=Sof(Br1)=Sof(C1)=Sof(C2)=Sof(C8)=Sof(H8)=Sof(C9)=Sof(H9)=Sof(C10)=
 Sof(C11)=Sof(H11)=Sof(O4)=Sof(C20)=Sof(H20A)=Sof(H20B)=Sof(H20C)=FVAR(1)
7.a Ternary CH refined with riding coordinates:
 C3(H3A), C3(H3B), C5(H5)
7.b Secondary CH2 refined with riding coordinates:
 C4(H4A,H4B), C22(H22A,H22B)
7.c Aromatic/amide H refined with riding coordinates:
 C8(H8), C9(H9), C11(H11), C8A(H8A), C9A(H9A), C11A(H11A), C13(H13), C14(H14),
 C16(H16), C17(H17), C24(H24), C25(H25), C26(H26), C27(H27), C28(H28)
7.d Idealised Me refined as rotating group:
 C18(H18A,H18B,H18C), C20(H20A,H20B,H20C), C21(H21A,H21B,H21C), C20A(H20D,H20E,
 H20F)
;
_shelx_res_checksum              64991
_shelx_hkl_checksum              85903
_olex2_submission_special_instructions 'No special instructions were received'