Scope of the Reactions of Indolyl- and Pyrrolyl-Tethered N-Sulfonyl-1,2,3-triazoles: Rhodium(II)-Catalyzed Synthesis of Indole- and Pyrrole-Fused Polycyclic Compounds.
Fu, Liangbing; Davies, Huw M. L.; Organic letters  (2017) –; doi:10.1021/acs.orglett.7b00180

data_1546600
_publ_section_title
;
 Scope of the Reactions of Indolyl- and Pyrrolyl-Tethered
 N-Sulfonyl-1,2,3-triazoles: Rhodium(II)-Catalyzed Synthesis of Indole-
 and Pyrrole-Fused Polycyclic Compounds.
;
_journal_name_full               'Organic letters'
_journal_paper_doi               10.1021/acs.orglett.7b00180
_journal_year                    2017
_chemical_formula_moiety         'C23 H27 N3 O4 S2'
_chemical_formula_sum            'C23 H27 N3 O4 S2'
_chemical_formula_weight         473.59
_space_group_crystal_system      monoclinic
_space_group_IT_number           4
_space_group_name_Hall           'P 2yb'
_space_group_name_H-M_alt        'P 1 21 1'
_symmetry_space_group_name_Hall  'P 2yb'
_symmetry_space_group_name_H-M   'P 1 21 1'
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     direct
_audit_creation_date             2015-03-23
_audit_creation_method
;
Olex2 1.2-dev
(compiled 2015.02.26 svn.r3159 for OlexSys, GUI svn.r5018)
;
_cell_angle_alpha                90
_cell_angle_beta                 92.183(2)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   8.4373(3)
_cell_length_b                   6.1045(2)
_cell_length_c                   22.2510(8)
_cell_measurement_reflns_used    7231
_cell_measurement_temperature    173(2)
_cell_measurement_theta_max      67.122
_cell_measurement_theta_min      3.977
_cell_volume                     1145.22(7)
_computing_cell_refinement       'SAINT v8.34A (Bruker, 2013)'
_computing_data_collection       'APEX2 v2011.2-4 (Bruker, 2011)'
_computing_data_reduction        'SAINT v8.34A (Bruker, 2013)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      173(2)
_diffrn_detector_area_resol_mean 512
_diffrn_measured_fraction_theta_full 0.927
_diffrn_measured_fraction_theta_max 0.927
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0367
_diffrn_reflns_av_unetI/netI     0.0460
_diffrn_reflns_Laue_measured_fraction_full 0.927
_diffrn_reflns_Laue_measured_fraction_max 0.927
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_k_min       -6
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_limit_l_min       -26
_diffrn_reflns_number            7517
_diffrn_reflns_point_group_measured_fraction_full 0.820
_diffrn_reflns_point_group_measured_fraction_max 0.820
_diffrn_reflns_theta_full        64.982
_diffrn_reflns_theta_max         64.982
_diffrn_reflns_theta_min         3.976
_diffrn_source                   'sealed tube'
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    2.403
_exptl_absorpt_correction_T_max  0.7529
_exptl_absorpt_correction_T_min  0.4533
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2014/5 (Bruker,2014/5) was used for absorption correction.
wR2(int) was 0.1207 before and 0.0609 after correction.
The Ratio of minimum to maximum transmission is 0.6021.
The \l/2 correction factor is Not present.
;
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.373
_exptl_crystal_description       prism
_exptl_crystal_F_000             500
_exptl_crystal_recrystallization_method
'The material was recrystallised from a mixture of hexane and diethyl ether by slow evaporation'
_exptl_crystal_size_max          0.752
_exptl_crystal_size_mid          0.353
_exptl_crystal_size_min          0.136
_refine_diff_density_max         0.350
_refine_diff_density_min         -0.255
_refine_diff_density_rms         0.052
_refine_ls_abs_structure_details
;
 Flack x determined using 1137 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.048(10)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.020
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     322
_refine_ls_number_reflns         3195
_refine_ls_number_restraints     64
_refine_ls_restrained_S_all      1.095
_refine_ls_R_factor_all          0.0385
_refine_ls_R_factor_gt           0.0378
_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^)+(0.0558P)^2^+0.5372P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0987
_refine_ls_wR_factor_ref         0.0994
_reflns_Friedel_coverage         0.602
_reflns_Friedel_fraction_full    0.688
_reflns_Friedel_fraction_max     0.688
_reflns_number_gt                3117
_reflns_number_total             3195
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            ol7b00180_si_002.cif
_cod_data_source_block           lfu-x-22
_cod_database_code               1546600
_shelx_estimated_absorpt_t_max   0.736
_shelx_estimated_absorpt_t_min   0.265
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2. Shared sites
{C1A, C1B}
{C4B, C4A}
3. Restrained distances
 C23-H23B
 0.99 with sigma of 0.02
 C4B-C1B
 1.52 with sigma of 0.005
 C4B-C1B
 1.52 with sigma of 0.005
 C4A-C1A
 1.52 with sigma of 0.005
 C8-H8A \\sim C8-H8B \\sim C7-H7A \\sim C7-H7B \\sim C9-H9A \\sim C9-H9B
 with sigma of 0.004
 C17-H17 \\sim C21-H21 \\sim C20-H20 \\sim C18-H18 \\sim C6-H6
 with sigma of 0.004
 C23-H23B \\sim C23-H23A \\sim C23-H23C
 with sigma of 0.004
 C4B-C3B \\sim C4A-C3A
 with sigma of 0.002
 N2B-C1B \\sim N2A-C1A
 with sigma of 0.002
4. Uiso/Uaniso restraints and constraints
: with sigma of 0.005 and sigma for terminal atoms of 0.01
: with sigma of 0.005 and sigma for terminal atoms of 0.01
: with sigma of 0.005 and sigma for terminal atoms of 0.01
: with sigma of 0.005 and sigma for terminal atoms of 0.01
Uiso(H8A) = Uiso(H7A) = Uiso(H7B) = Uiso(H9A) = Uiso(H8B) = Uiso(H9B)
Uiso(H18) = Uiso(H17) = Uiso(H21) = Uiso(H20) = Uiso(H6)
Uiso(H23B) = Uiso(H23A) = Uiso(H23C)
Uiso(C2A) = Uiso(C2B)
Uiso(C3A) = Uiso(C3B)
Uiso(C13A) = Uiso(C13B)
Uiso(C12A) = Uiso(C12B)
Uiso(C11A) = Uiso(C11B)
Uiso(C10A) = Uiso(C10B)
Uiso(C15A) = Uiso(C15B)
Uiso(C14A) = Uiso(C14B)
Uiso(N2A) = Uiso(N2B)
Uanis(C1A) = Uanis(C1B)
Uanis(C4A) = Uanis(C4B)
Uiso(C2B) = Uiso(C2A)
Uanis(C1A) = Uanis(C1B)
Uanis(C4B) = Uanis(C4A)
5. Rigid body (RIGU) restrains
 C2A, C3A
 with sigma for 1-2 distances of 0.002 and sigma for 1-3 distances of 0.002
 C3A, C13A
 with sigma for 1-2 distances of 0.002 and sigma for 1-3 distances of 0.002
 C12A, C13A
 with sigma for 1-2 distances of 0.002 and sigma for 1-3 distances of 0.002
 C12A, C11A
 with sigma for 1-2 distances of 0.002 and sigma for 1-3 distances of 0.002
 C11A, C10A, C2A
 with sigma for 1-2 distances of 0.002 and sigma for 1-3 distances of 0.002
6. Same fragment restrains
{C14B, N2B, C2B, C3B, C4B, C1B, C10B, C11B, C15B, C12B, C13B} sigma for 1-2:
0.006, 1-3: 0.009
as
{C14A, N2A, C2A, C3A, C4A, C1A, C10A, C11A, C15A, C12A, C13A}
7. Others
 Sof(C14B)=Sof(H14D)=Sof(H14E)=Sof(H14F)=Sof(N2B)=Sof(C2B)=Sof(C3B)=Sof(C4B)=
 Sof(C1B)=Sof(H1B)=Sof(C10B)=Sof(H10B)=Sof(C11B)=Sof(C15B)=Sof(H15D)=Sof(H15E)=
 Sof(H15F)=Sof(C12B)=Sof(H12B)=Sof(C13B)=Sof(H13B)=1-FVAR(1)
 Sof(C14A)=Sof(H14A)=Sof(H14B)=Sof(H14C)=Sof(N2A)=Sof(C2A)=Sof(C3A)=Sof(C4A)=
 Sof(C1A)=Sof(H1A)=Sof(C10A)=Sof(H10A)=Sof(C11A)=Sof(C15A)=Sof(H15A)=Sof(H15B)=
 Sof(H15C)=Sof(C12A)=Sof(H12A)=Sof(C13A)=Sof(H13A)=FVAR(1)
8.a Ternary CH refined with riding coordinates:
 C1A(H1A), C1B(H1B)
8.b Aromatic/amide H refined with riding coordinates:
 C10A(H10A), C12A(H12A), C13A(H13A), C10B(H10B), C12B(H12B), C13B(H13B)
8.c Idealised Me refined as rotating group:
 C14A(H14A,H14B,H14C), C15A(H15A,H15B,H15C), C14B(H14D,H14E,H14F), C15B(H15D,
 H15E,H15F), C22(H22A,H22B,H22C)
;
_shelx_res_checksum              53933
_shelx_hkl_checksum              54778
_shelx_shelxl_version_number     2014/7
_olex2_diffrn_ambient_temperature_device 'Oxford Cryosystems'
_olex2_exptl_crystal_mounting_method
'The crystal was mounted on a loop with paratone oil'
_olex2_submission_original_sample_id LFU-X-22
_olex2_submission_special_instructions 'No special instructions were received'