Cascade Reaction of 1,1-Enediamines with 2-Benzylidene-1<i>H</i>-indene-1,3(2<i>H</i>)-diones: Selective Synthesis of Indenodihydropyridine and Indenopyridine Compounds.
Luo, Qin; Huang, Rong; Xiao, Qiang; Kong, Ling-Bin; Lin, Jun; Yan, Sheng-Jiao; ACS omega 4 (2019) 6637–6646; doi:10.1021/acsomega.9b00407

data_4515080
_publ_section_title
;
 Cascade Reaction of 1,1-Enediamines with
 2-Benzylidene-1<i>H</i>-indene-1,3(2<i>H</i>)-diones: Selective Synthesis
 of Indenodihydropyridine and Indenopyridine Compounds.
;
_journal_issue                   4
_journal_name_full               'ACS omega'
_journal_page_first              6637
_journal_page_last               6646
_journal_paper_doi               10.1021/acsomega.9b00407
_journal_volume                  4
_journal_year                    2019
_chemical_formula_moiety         'C26 H18 Cl N3 O3, C2 H6 O S'
_chemical_formula_sum            'C28 H24 Cl N3 O4 S'
_chemical_formula_weight         534.01
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2yn'
_space_group_name_H-M_alt        'P 1 21/n 1'
_symmetry_space_group_name_Hall  '-P 2yn'
_symmetry_space_group_name_H-M   'P 1 21/n 1'
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     dual
_audit_creation_date             2018-03-21
_audit_creation_method
;
Olex2 1.2-alpha
(compiled 2018.02.02 svn.r3481 for OlexSys, GUI svn.r5480)
;
_cell_angle_alpha                90
_cell_angle_beta                 95.115(3)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   12.2079(8)
_cell_length_b                   9.6867(6)
_cell_length_c                   21.9929(15)
_cell_measurement_reflns_used    6976
_cell_measurement_temperature    298.01
_cell_measurement_theta_max      26.39
_cell_measurement_theta_min      2.30
_cell_volume                     2590.4(3)
_computing_cell_refinement       'SAINT v8.37A (Bruker, 2015)'
_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  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_diffrn_ambient_temperature      298.01
_diffrn_measured_fraction_theta_full 0.994
_diffrn_measured_fraction_theta_max 0.993
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0657
_diffrn_reflns_av_unetI/netI     0.0395
_diffrn_reflns_Laue_measured_fraction_full 0.994
_diffrn_reflns_Laue_measured_fraction_max 0.993
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       27
_diffrn_reflns_limit_l_min       -27
_diffrn_reflns_number            34050
_diffrn_reflns_point_group_measured_fraction_full 0.994
_diffrn_reflns_point_group_measured_fraction_max 0.993
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.440
_diffrn_reflns_theta_min         2.299
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.268
_exptl_absorpt_correction_T_max  0.7454
_exptl_absorpt_correction_T_min  0.6230
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
'SADABS-2016/2 (Bruker,2016/2) was used for absorption correction. wR2(int) was 0.0683 before and 0.0543 after correction. The Ratio of minimum to maximum transmission is 0.8358. The \l/2 correction factor is Not present.'
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.369
_exptl_crystal_description       block
_exptl_crystal_F_000             1112
_exptl_crystal_size_max          0.28
_exptl_crystal_size_mid          0.26
_exptl_crystal_size_min          0.24
_refine_diff_density_max         0.599
_refine_diff_density_min         -0.663
_refine_diff_density_rms         0.051
_refine_ls_extinction_coef       0.0060(10)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2014/7 (Sheldrick 2014'
_refine_ls_goodness_of_fit_ref   1.025
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     337
_refine_ls_number_reflns         5308
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.025
_refine_ls_R_factor_all          0.1035
_refine_ls_R_factor_gt           0.0570
_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^)+(0.0714P)^2^+1.8645P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1404
_refine_ls_wR_factor_ref         0.1686
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3273
_reflns_number_total             5308
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            ao9b00407_si_002.cif
_cod_data_source_block           mo_0319_7_0m
_cod_database_code               4515080
_shelx_shelxl_version_number     2014/7
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All N(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Riding coordinates:
 N3(H3)
2.b Secondary CH2 refined with riding coordinates:
 C17(H17A,H17B), C18(H18A,H18B)
2.c Aromatic/amide H refined with riding coordinates:
 C20(H20), C25(H25), C3(H3A), C21(H21), C2(H2), C13(H13), C26(H26), C22(H22),
 C24(H24), C16(H16), C14(H14), C23(H23), C15(H15)
2.d Idealised Me refined as rotating group:
 C27(H27A,H27B,H27C), C28(H28A,H28B,H28C)
;
_shelx_res_checksum              80458
_shelx_hkl_checksum              22835
_olex2_submission_special_instructions 'No special instructions were received'