A Au(i)-catalyzed hydrogen bond-directed tandem strategy to synthesize indeno-chromen-4-one and indeno-quinolin-4-one derivatives.
Jiang, Chongguo; Xiong, Zhiling; Jin, Shengfei; Gao, Peng; Tang, Yingzhan; Wang, Yanshi; Du, Chuan; Wang, Xiaoyu; Liu, Yang; Lin, Bin; Liu, Yongxiang; Cheng, Maosheng; Chemical communications (Cambridge, England) 52 (2016) 11516–11519; doi:10.1039/c6cc05391b

data_7124895
_publ_section_title
;
 A Au(i)-catalyzed hydrogen bond-directed tandem strategy to synthesize
 indeno-chromen-4-one and indeno-quinolin-4-one derivatives.
;
_journal_issue                   77
_journal_name_full               'Chemical communications (Cambridge, England)'
_journal_page_first              11516
_journal_page_last               11519
_journal_paper_doi               10.1039/c6cc05391b
_journal_volume                  52
_journal_year                    2016
_chemical_formula_moiety         'C19 H16 O3'
_chemical_formula_sum            'C19 H16 O3'
_chemical_formula_weight         292.32
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     iterative
_audit_creation_date             2015-07-29
_audit_creation_method
;
Olex2 1.2
(compiled 2015.01.26 svn.r3150 for OlexSys, GUI svn.r4998)
;
_audit_update_record
;
2016-06-28 deposited with the CCDC.
2016-08-12 downloaded from the CCDC.
;
_cell_angle_alpha                67.824(9)
_cell_angle_beta                 77.107(7)
_cell_angle_gamma                79.532(7)
_cell_formula_units_Z            2
_cell_length_a                   7.0903(5)
_cell_length_b                   10.2299(10)
_cell_length_c                   11.0836(10)
_cell_measurement_reflns_used    1672
_cell_measurement_temperature    180.01(10)
_cell_measurement_theta_max      29.2110
_cell_measurement_theta_min      3.8350
_cell_volume                     721.45(12)
_computing_cell_refinement
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.32 (release 02-08-2013 CrysAlis171 .NET)
(compiled Aug  2 2013,16:46:58)
;
_computing_data_collection
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CrysAlisPro, Agilent Technologies,
Version 1.171.36.32 (release 02-08-2013 CrysAlis171 .NET)
(compiled Aug  2 2013,16:46:58)
;
_computing_data_reduction
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CrysAlisPro, Agilent Technologies,
Version 1.171.36.32 (release 02-08-2013 CrysAlis171 .NET)
(compiled Aug  2 2013,16:46:58)
;
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2008)'
_computing_structure_solution
;
Superflip (Palatinus & Chapuis, 2007;Palatinus & van der Lee, 2008;
Palatinus et al., 2012)
;
_diffrn_ambient_temperature      180.01(10)
_diffrn_detector_area_resol_mean 10.3914
_diffrn_measured_fraction_theta_full 0.994
_diffrn_measured_fraction_theta_max 0.991
_diffrn_measurement_details
;
  1 omega   35.00   99.00   1.0000    3.0000
omega____ theta____ kappa____ phi______ frames
    -       10.7017 -178.0000  150.0000 64

  2 omega  -79.00   18.00   1.0000    3.0000
omega____ theta____ kappa____ phi______ frames
    -      -11.7954  -57.0000  150.0000 97

  3 omega  -40.00   59.00   1.0000    3.0000
omega____ theta____ kappa____ phi______ frames
    -      -11.7954   57.0000  -60.0000 99
;
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, Atlas'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_UB_11      0.0187120000
_diffrn_orient_matrix_UB_12      0.0597537000
_diffrn_orient_matrix_UB_13      0.0114730000
_diffrn_orient_matrix_UB_21      0.0212313000
_diffrn_orient_matrix_UB_22      0.0366402000
_diffrn_orient_matrix_UB_23      -0.0691792000
_diffrn_orient_matrix_UB_31      -0.0992738000
_diffrn_orient_matrix_UB_32      0.0275557000
_diffrn_orient_matrix_UB_33      -0.0002567000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0237
_diffrn_reflns_av_unetI/netI     0.0459
_diffrn_reflns_Laue_measured_fraction_full 0.994
_diffrn_reflns_Laue_measured_fraction_max 0.991
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            4530
_diffrn_reflns_point_group_measured_fraction_full 0.994
_diffrn_reflns_point_group_measured_fraction_max 0.991
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.021
_diffrn_reflns_theta_min         3.289
_diffrn_source                   'SuperNova (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    0.090
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.44010
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.32 (release 02-08-2013 CrysAlis171 .NET)
(compiled Aug  2 2013,16:46:58)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_density_diffrn    1.346
_exptl_crystal_F_000             308
_exptl_crystal_size_max          0.1
_exptl_crystal_size_mid          0.1
_exptl_crystal_size_min          0.05
_refine_diff_density_max         0.568
_refine_diff_density_min         -0.276
_refine_diff_density_rms         0.052
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.100
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     202
_refine_ls_number_reflns         2826
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.100
_refine_ls_R_factor_all          0.0736
_refine_ls_R_factor_gt           0.0538
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0536P)^2^+0.4260P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1363
_refine_ls_wR_factor_ref         0.1531
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2113
_reflns_number_total             2826
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c6cc05391b2.cif
_cod_data_source_block           exp_5651
_cod_database_code               7124895
_shelxl_version_number           2014-3
_chemical_oxdiff_formula         'C1 H1 O1'
_shelx_estimated_absorpt_t_max   0.995
_shelx_estimated_absorpt_t_min   0.991
_reflns_odcompleteness_completeness 99.09
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     25.97
_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.a Ternary CH refined with riding coordinates:
 C8(H8)
2.b Aromatic/amide H refined with riding coordinates:
 C3(H3), C4(H4), C5(H5), C6(H6), C12(H12), C14(H14)
2.c Idealised Me refined as rotating group:
 C17(H17A,H17B,H17C), C18(H18A,H18B,H18C), C19(H19A,H19B,H19C)
;
_shelx_res_checksum              48264
_olex2_submission_special_instructions 'No special instructions were received'