Divergent Syntheses of Spiroindanones and 2-Substituted 1-Indanones by Ruthenium-Catalyzed Tandem Coupling and Cyclization of Aromatic Acids with α,β-Unsaturated Ketones.
Wang, Jia-Ni; Chen, Si-Qi; Liu, Zhong-Wen; Shi, Xian-Ying; The Journal of organic chemistry 84 (2019) 1348–1362; doi:10.1021/acs.joc.8b02820

data_4037557
_publ_section_title
;
 Divergent Syntheses of Spiroindanones and 2-Substituted 1-Indanones by
 Ruthenium-Catalyzed Tandem Coupling and Cyclization of Aromatic Acids
 with \a,\b-Unsaturated Ketones.
;
_journal_issue                   3
_journal_name_full               'The Journal of organic chemistry'
_journal_page_first              1348
_journal_page_last               1362
_journal_paper_doi               10.1021/acs.joc.8b02820
_journal_volume                  84
_journal_year                    2019
_chemical_formula_moiety         'C19 H22 O2'
_chemical_formula_sum            'C19 H22 O2'
_chemical_formula_weight         282.36
_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'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2018-10-17
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_cell_angle_alpha                90
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_cell_angle_gamma                90
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_cell_length_a                   12.8547(16)
_cell_length_b                   16.926(2)
_cell_length_c                   7.0925(9)
_cell_measurement_reflns_used    9960
_cell_measurement_temperature    153
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_cell_measurement_theta_min      4.386
_cell_volume                     1506.6(3)
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_computing_data_reduction        'SAINT v8.37A (Bruker, 2015)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL (Sheldrick, 2008)'
_computing_structure_solution    'XT (Sheldrick, 2015)'
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_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.948
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0534
_diffrn_reflns_av_unetI/netI     0.0324
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.948
_diffrn_reflns_limit_h_max       15
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_diffrn_reflns_limit_k_min       -20
_diffrn_reflns_limit_l_max       8
_diffrn_reflns_limit_l_min       -7
_diffrn_reflns_number            20710
_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.948
_diffrn_reflns_theta_full        67.679
_diffrn_reflns_theta_max         68.352
_diffrn_reflns_theta_min         2.610
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.619
_exptl_absorpt_correction_T_max  0.7531
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_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
'SADABS-2016/2 (Bruker,2016/2) was used for absorption correction. wR2(int) was 0.1178 before and 0.0799 after correction. The Ratio of minimum to maximum transmission is 0.8688. The \l/2 correction factor is Not present.'
_exptl_crystal_colour            'clear light yellow'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    yellow
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_exptl_crystal_F_000             608
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_exptl_crystal_size_min          0.3
_refine_diff_density_max         0.793
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_refine_ls_extinction_method     none
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_refine_ls_number_reflns         2719
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.087
_refine_ls_R_factor_all          0.0998
_refine_ls_R_factor_gt           0.0989
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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^)+(0.1493P)^2^+3.8362P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2813
_refine_ls_wR_factor_ref         0.2819
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2649
_reflns_number_total             2719
_reflns_threshold_expression     'I > 2\s(I)'
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_cod_data_source_block           s
_cod_database_code               4037557
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_shelx_estimated_absorpt_t_min   0.747
_olex2_refinement_description
;
1. Twinned data refinement
 Scales: 0.9958(7)
 0.0042(7)
2. 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
3.a Secondary CH2 refined with riding coordinates:
 C006(H00A,H00B), C00D(H00F,H00G), C00H(H00L,H00M), C00J(H00O,H00P)
3.b Aromatic/amide H refined with riding coordinates:
 C00F(H00K), C00I(H00N)
3.c Idealised Me refined as rotating group:
 C00B(H00C,H00D,H00E), C00E(H00H,H00I,H00J), C00K(H00Q,H00R,H00S), C00L(H00T,
 H00U,H00V)
;
_shelx_res_checksum              51864
_shelx_hkl_checksum              68984
_olex2_submission_special_instructions 'No special instructions were received'