Gold-catalyzed chemo- and diastereoselective C(sp(2))-H functionalization of enaminones for the synthesis of pyrrolo[3,4-c]-quinolin-1-one derivatives.
Zhao, Yulei; Duan, Qizhao; Zhou, Yuanyuan; Yao, Qiyi; Li, Yanzhong; Organic & biomolecular chemistry 14 (2016) 2177–2181; doi:10.1039/c5ob02556g

data_7154905
_publ_section_title
;
 Gold-catalyzed chemo- and diastereoselective C(sp(2))-H functionalization
 of enaminones for the synthesis of pyrrolo[3,4-c]-quinolin-1-one
 derivatives.
;
_journal_issue                   7
_journal_name_full               'Organic &amp; biomolecular chemistry'
_journal_page_first              2177
_journal_page_last               2181
_journal_paper_doi               10.1039/c5ob02556g
_journal_volume                  14
_journal_year                    2016
_chemical_formula_moiety         'C24 H16 Cl2 N2 O2, C H Cl3'
_chemical_formula_sum            'C25 H17 Cl5 N2 O2'
_chemical_formula_weight         554.65
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_audit_creation_date             2014-12-16
_audit_creation_method
;
Olex2 1.2
(compiled 2014.07.22 svn.r2960 for OlexSys, GUI svn.r4862)
;
_audit_update_record
;
2015-11-16 deposited with the CCDC.
2016-01-12 downloaded from the CCDC.
;
_cell_angle_alpha                66.5140(10)
_cell_angle_beta                 85.3090(10)
_cell_angle_gamma                89.3010(10)
_cell_formula_units_Z            2
_cell_length_a                   7.0166(5)
_cell_length_b                   13.2800(9)
_cell_length_c                   13.9998(10)
_cell_measurement_reflns_used    4397
_cell_measurement_temperature    130
_cell_measurement_theta_max      30.526
_cell_measurement_theta_min      2.731
_cell_volume                     1192.13(15)
_computing_cell_refinement       'SAINT v7.68A (Bruker, 2009)'
_computing_data_reduction        'SAINT v7.68A (Bruker, 2009)'
_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    'ShelXS (Sheldrick, 2008)'
_diffrn_ambient_temperature      130
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.991
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0187
_diffrn_reflns_av_unetI/netI     0.0346
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.991
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            12148
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.991
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         30.572
_diffrn_reflns_theta_min         1.672
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.636
_exptl_absorpt_correction_T_max  0.7461
_exptl_absorpt_correction_T_min  0.6543
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2008/1 (Bruker,2008) was used for absorption correction.
wR2(int) was 0.0729 before and 0.0297 after correction.
The Ratio of minimum to maximum transmission is 0.8770.
The \l/2 correction factor is 0.0015.
;
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.545
_exptl_crystal_description       block
_exptl_crystal_F_000             564
_exptl_crystal_size_max          0.35
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.18
_refine_diff_density_max         1.570
_refine_diff_density_min         -1.663
_refine_diff_density_rms         0.088
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.053
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     308
_refine_ls_number_reflns         7236
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.053
_refine_ls_R_factor_all          0.0681
_refine_ls_R_factor_gt           0.0537
_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^)+(0.0682P)^2^+1.0819P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1357
_refine_ls_wR_factor_ref         0.1467
_reflns_Friedel_coverage         0.000
_reflns_number_gt                5734
_reflns_number_total             7236
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c5ob02556g2.cif
_cod_data_source_block           mo_dm14733_0m
_cod_depositor_comments
'Adding full bibliography for 7154904--7154905.cif.'
_cod_database_code               7154905
_shelxl_version_number           2014-3
_shelx_estimated_absorpt_t_max   0.894
_shelx_estimated_absorpt_t_min   0.808
_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.a Ternary CH refined with riding coordinates:
 C25(H25)
2.b Secondary CH2 refined with riding coordinates:
 C11(H11A,H11B)
2.c Aromatic/amide H refined with riding coordinates:
 C5(H5), C7(H7), C13(H13), C14(H14), C15(H15), C16(H16), C17(H17), C19(H19),
 C20(H20), C22(H22), C23(H23)
2.d Idealised Me refined as rotating group:
 C24(H24A,H24B,H24C)
;
_shelx_res_checksum              90033
_olex2_submission_special_instructions 'No special instructions were received'