Regioselective Tandem [4 + 1]-[4 + 2] Synthesis of Amino-Substituted Dihydroxanthones and Xanthones.
Bornadiego, Ana; Díaz, Jesús; Marcos, Carlos F.; The Journal of organic chemistry 80 (2015) 6165–6172; doi:10.1021/acs.joc.5b00658

data_4031058
_publ_section_title
;
 Regioselective Tandem [4 + 1]-[4 + 2] Synthesis of Amino-Substituted
 Dihydroxanthones and Xanthones.
;
_journal_issue                   12
_journal_name_full               'The Journal of organic chemistry'
_journal_page_first              6165
_journal_page_last               6172
_journal_paper_doi               10.1021/acs.joc.5b00658
_journal_volume                  80
_journal_year                    2015
_chemical_formula_moiety         'C24 H25 N O6'
_chemical_formula_sum            'C24 H25 N O6'
_chemical_formula_weight         423.47
_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_Int_Tables_number      2
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_primary     iterative
_audit_creation_date             2014-01-16
_audit_creation_method
;
Olex2 1.2
(compiled 2013.11.15 svn.r2834 for OlexSys, GUI svn.r4720)
;
_cell_angle_alpha                67.348
_cell_angle_beta                 71.132
_cell_angle_gamma                86.941(1)
_cell_formula_units_Z            4
_cell_length_a                   12.6115(2)
_cell_length_b                   13.0653(2)
_cell_length_c                   14.4113(2)
_cell_measurement_reflns_used    9921
_cell_measurement_temperature    170.0
_cell_measurement_theta_max      30.08
_cell_measurement_theta_min      2.88
_cell_volume                     2066.77(5)
_computing_data_reduction        'SAINT v7.60A (Bruker, 2009)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'olex2.refine (Bourhis et al., 2013)'
_computing_structure_solution    'olex2.solve (Bourhis et al., 2013)'
_diffrn_ambient_temperature      170.0
_diffrn_measured_fraction_theta_full 0.9908
_diffrn_measured_fraction_theta_max 0.9908
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0146
_diffrn_reflns_av_unetI/netI     0.0240
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_h_min       -17
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            21242
_diffrn_reflns_theta_full        30.0919
_diffrn_reflns_theta_max         30.09
_diffrn_reflns_theta_min         2.88
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.098
_exptl_absorpt_correction_T_max  0.7460
_exptl_absorpt_correction_T_min  0.6912
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2008/1 (Bruker,2008) was used for absorption correction.
wR2(int) was 0.0715 before and 0.0253 after correction.
The Ratio of minimum to maximum transmission is 0.9265.
The \l/2 correction factor is Not present.
;
_exptl_crystal_colour            yellow
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.3608
_exptl_crystal_description       prismatic
_exptl_crystal_F_000             896.5194
_exptl_crystal_size_max          0.4
_exptl_crystal_size_mid          0.4
_exptl_crystal_size_min          0.24
_refine_diff_density_max         0.5126
_refine_diff_density_min         -0.2525
_refine_diff_density_rms         0.0557
_refine_ls_d_res_high            0.7088
_refine_ls_d_res_low             7.0800
_refine_ls_goodness_of_fit_ref   1.1487
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_constraints    78
_refine_ls_number_parameters     564
_refine_ls_number_reflns         12058
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.1487
_refine_ls_R_factor_all          0.0540
_refine_ls_R_factor_gt           0.0434
_refine_ls_shift/su_max          0.0006
_refine_ls_shift/su_mean         0.0000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.1P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1384
_refine_ls_wR_factor_ref         0.1506
_reflns_Friedel_coverage         0.0
_reflns_limit_h_max              17
_reflns_limit_h_min              -16
_reflns_limit_k_max              18
_reflns_limit_k_min              -16
_reflns_limit_l_max              20
_reflns_limit_l_min              0
_reflns_number_gt                9892
_reflns_number_total             12058
_reflns_threshold_expression     I>=2u(I)
_cod_data_source_file            jo5b00658_si_002.cif
_cod_data_source_block           ABS3371_0m
_cod_depositor_comments          'Adding full bibliography for 4031058.cif.'
_cod_database_code               4031058
_cell_ambient_temperature        170.0
_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 Ternary CH refined with riding coordinates:
 C17(H17), C1e(H1e)
2.b Secondary CH2 refined with riding coordinates:
 C1f(H1fa,H1fb), C1p(H1pa,H1pb), C1v(H1va,H1vb), C24(H24a,H24b), C25(H25a,
 H25b), C27(H27a,H27b), C28(H28a,H28b), C2b(H2ba,H2bb), C2d(H2da,H2db),
 C2e(H2ea,H2eb)
2.c Aromatic/amide H refined with riding coordinates:
 N9(H9), N11(H11), C15(H15), C1m(H1m), C1n(H1n), C1o(H1o), C1r(H1r), C1t(H1t),
 C20(H20), C21(H21)
2.d Idealised Me refined as rotating group:
 C1u(H1ua,H1ub,H1uc), C23(H23a,H23b,H23c), C29(H29a,H29b,H29c), C2a(H2aa,H2ab,
 H2ac), C2c(H2ca,H2cb,H2cc), C2f(H2fa,H2fb,H2fc)
;