Synthesis of Conjugated Polycyclic Quinoliniums by Rhodium(III)-Catalyzed Multiple C-H Activation and Annulation of Arylpyridiniums with Alkynes.
Ge, Qingmei; Hu, Yang; Li, Bin; Wang, Baiquan; Organic letters 18 (2016) 2483–2486; doi:10.1021/acs.orglett.6b01055

data_1543237
_publ_section_title
;
 Synthesis of Conjugated Polycyclic Quinoliniums by Rhodium(III)-Catalyzed
 Multiple C-H Activation and Annulation of Arylpyridiniums with Alkynes.
;
_journal_issue                   10
_journal_name_full               'Organic letters'
_journal_page_first              2483
_journal_page_last               2486
_journal_paper_doi               10.1021/acs.orglett.6b01055
_journal_volume                  18
_journal_year                    2016
_chemical_formula_moiety         'C39 H26 N, C F3 O3 S'
_chemical_formula_sum            'C40 H26 F3 N O3 S'
_chemical_formula_weight         657.68
_chemical_name_systematic
;
 ? 
;
_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'
_symmetry_space_group_name_Hall  '-C 2yc'
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_atom_sites_solution_hydrogens   geom
_audit_creation_date             2016-04-05
_audit_creation_method
;
Olex2 1.2
(compiled 2015.09.30 svn.r3233 for OlexSys, GUI svn.r5155)
;
_cell_angle_alpha                90
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_cell_formula_units_Z            4
_cell_length_a                   26.374(3)
_cell_length_b                   7.9979(9)
_cell_length_c                   15.0584(18)
_cell_measurement_reflns_used    5446
_cell_measurement_temperature    113
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_computing_cell_refinement
;
CrystalClear-SM Expert 2.1 b42 (Rigaku, 2015)
;
_computing_data_collection
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CrystalClear-SM Expert 2.1 b42 (Rigaku, 2015)
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CrystalClear-SM Expert 2.1 b42 (Rigaku, 2015)
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_diffrn_measurement_details
;
scan:
    Number of images: 360
               Slice: -105.0000 - 75.0000
         Image width: 0.5000
            Exp time: 2.0000
       Rotation axis: Omega
               Omega: 0.0000
                 Chi: 45.0000
                 Phi: 0.0000
                 XTD: 44.9781
              2theta: -15.0987
scan:
    Number of images: 360
               Slice: -105.0000 - 75.0000
         Image width: 0.5000
            Exp time: 2.0000
       Rotation axis: Omega
               Omega: 0.0000
                 Chi: 45.0000
                 Phi: 90.0000
                 XTD: 44.9781
              2theta: -15.0987
scan:
    Number of images: 360
               Slice: -105.0000 - 75.0000
         Image width: 0.5000
            Exp time: 2.0000
       Rotation axis: Omega
               Omega: 0.0000
                 Chi: 45.0000
                 Phi: 180.0000
                 XTD: 44.9781
              2theta: -15.0987
;
_diffrn_measurement_device
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AFC10: Fixed Chi 2 circle
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_diffrn_measurement_device_type  'Rigaku Pilatus 200K'
_diffrn_measurement_method       '\w scans'
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_diffrn_orient_matrix_UB_11      -0.004288
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_diffrn_radiation_monochromator  Confocal
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0194
_diffrn_reflns_av_unetI/netI     0.0106
_diffrn_reflns_Laue_measured_fraction_full 0.995
_diffrn_reflns_Laue_measured_fraction_max 0.995
_diffrn_reflns_limit_h_max       31
_diffrn_reflns_limit_h_min       -31
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_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            15132
_diffrn_reflns_point_group_measured_fraction_full 0.995
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_diffrn_reflns_theta_full        25.019
_diffrn_reflns_theta_max         25.019
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_diffrn_source                   'Rotating Anode'
_diffrn_source_current           24.0
_diffrn_source_power             1.2
_diffrn_source_voltage           50.0
_exptl_absorpt_coefficient_mu    0.164
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.919
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'REQAB (Rigaku, 1998)'
_exptl_crystal_colour            Colorless
_exptl_crystal_density_diffrn    1.396
_exptl_crystal_density_method    "'not measured'"
_exptl_crystal_description       Prism
_exptl_crystal_F_000             1360
_exptl_crystal_preparation       Fiber
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.18
_exptl_crystal_size_min          0.12
_refine_diff_density_max         0.732
_refine_diff_density_min         -0.334
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_refine_ls_extinction_coef       0.0037(5)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2014/8 (Sheldrick 2014'
_refine_ls_goodness_of_fit_ref   1.046
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     248
_refine_ls_number_reflns         2751
_refine_ls_number_restraints     66
_refine_ls_restrained_S_all      1.130
_refine_ls_R_factor_all          0.0531
_refine_ls_R_factor_gt           0.0510
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_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0589P)^2^+6.2077P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1303
_refine_ls_wR_factor_ref         0.1317
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2577
_reflns_number_total             2751
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            ol6b01055_si_002.cif
_cod_data_source_block           shelx
_cod_depositor_comments
;
The following automatic conversions were performed:

'_exptl_absorpt_correction_type' value 'Multi-scan' changed to
'multi-scan' according to
/usr/data/users/saulius/crontab/automatic-downloads/rss-feeds/ACS/lib/dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.2 from 2011-04-26.

Automatic conversion script
Id: cif_fix_values 4268 2015-11-12 08:31:59Z antanas 

 Adding full bibliography for 1543237.cif.
;
_cod_database_code               1543237
_shelx_estimated_absorpt_t_max   0.981
_shelx_estimated_absorpt_t_min   0.968
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
2. Shared sites
{C1, N1}
3. Restrained distances
 C21-F1 = C21-F2 = C21-F3
 1.35 with sigma of 0.01
 F1-F2 \\sim F1-F3 \\sim F2-F3
 with sigma of 0.01
 S1-O1 \\sim S1-O2 \\sim S1-O3
 with sigma of 0.01
 O1-O2 \\sim O1-O3 \\sim O2-O3
 with sigma of 0.01
 F1-S1 \\sim F2-S1 \\sim F3-S1
 with sigma of 0.01
 C21-O1 \\sim C21-O2 \\sim C21-O3
 with sigma of 0.01
4. Uiso/Uaniso restraints and constraints
Uanis(S1) \\sim Ueq, Uanis(C21) \\sim Ueq, Uanis(F1) \\sim Ueq, Uanis(F2) \\sim
Ueq, Uanis(F3) \\sim Ueq, Uanis(O1) \\sim Ueq, Uanis(O2) \\sim Ueq, Uanis(O3)
\\sim Ueq: with sigma of 0.01 and sigma for terminal atoms of 0.02
Uanis(S1) = Uanis(C21)
Uanis(C1) = Uanis(N1)
5. Others
 Fixed Sof: N1(0.5) C1(0.5) S1(0.5) O1(0.5) O2(0.5) O3(0.5) F1(0.5) F2(0.5)
 F3(0.5) C21(0.5)
6.a Aromatic/amide H refined with riding coordinates:
 C3(H3), C4(H4), C5(H5), C9(H9), C10(H10), C11(H11), C12(H12), C13(H13),
 C16(H16), C17(H17), C18(H18), C19(H19), C20(H20)
;
_shelx_res_checksum              77948
_shelx_hkl_checksum              52623
_shelx_shelxl_version_number     2014/8
_olex2_submission_special_instructions 'No special instructions were received'