DBU-promoted cascade phosphorylation/cyclization for the synthesis of phosphorylated 3-aminoindoles.
Xu, Dong-Ping; Huang, Fei; Jin, Li-Zhen; Huang, Meng-Ya; Zhang, Wu; Chemical communications (Cambridge, England) 61 (2025) 4816–4819; doi:10.1039/d5cc00224a

data_7134280
_publ_section_title
;
 DBU-promoted cascade phosphorylation/cyclization for the synthesis of
 phosphorylated 3-aminoindoles.
;
_journal_issue                   25
_journal_name_full               'Chemical communications (Cambridge, England)'
_journal_page_first              4816
_journal_page_last               4819
_journal_paper_doi               10.1039/d5cc00224a
_journal_volume                  61
_journal_year                    2025
_chemical_formula_moiety         'C26 H21 N2 O P, C H4 O'
_chemical_formula_sum            'C27 H25 N2 O2 P'
_chemical_formula_weight         440.46
_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   mixed
_atom_sites_solution_primary     dual
_audit_creation_date             2024-09-26
_audit_creation_method
;
Olex2 1.5-alpha
(compiled 2024.02.16 svn.r378c4104 for OlexSys, GUI svn.r6928)
;
_audit_update_record
;
2024-09-26 deposited with the CCDC.	2025-02-24 downloaded from the CCDC.
;
_cell_angle_alpha                72.992(7)
_cell_angle_beta                 78.674(6)
_cell_angle_gamma                80.115(6)
_cell_formula_units_Z            2
_cell_length_a                   8.3695(12)
_cell_length_b                   10.144(2)
_cell_length_c                   14.956(3)
_cell_measurement_reflns_used    9486
_cell_measurement_temperature    297.15
_cell_measurement_theta_max      27.433
_cell_measurement_theta_min      2.861
_cell_volume                     1181.7(4)
_computing_cell_refinement       'SAINT v8.37A (Bruker, 2015)'
_computing_data_reduction        'SAINT v8.37A (Bruker, 2015)'
_computing_molecular_graphics    'Olex2 1.5-alpha (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5-alpha (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2019/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_diffrn_ambient_temperature      297.15
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.999
_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  0.0520
_diffrn_reflns_av_unetI/netI     0.0293
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            46840
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.480
_diffrn_reflns_theta_min         2.861
_diffrn_source_current           30.0
_diffrn_source_power             1.5
_diffrn_source_voltage           50.0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.142
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_correction_T_min  0.6352
_exptl_absorpt_correction_type   none
_exptl_absorpt_process_details
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.1160 before and 0.0678 after correction.
The Ratio of minimum to maximum transmission is 0.8519.
The \l/2 correction factor is Not present.
;
_exptl_crystal_colour            'clear light black'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    black
_exptl_crystal_density_diffrn    1.238
_exptl_crystal_description       block
_exptl_crystal_F_000             464
_exptl_crystal_size_max          0.22
_exptl_crystal_size_mid          0.21
_exptl_crystal_size_min          0.2
_refine_diff_density_max         0.303
_refine_diff_density_min         -0.452
_refine_diff_density_rms         0.087
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.078
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     292
_refine_ls_number_reflns         5408
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.078
_refine_ls_R_factor_all          0.0853
_refine_ls_R_factor_gt           0.0621
_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^)+(0.0539P)^2^+1.2518P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1422
_refine_ls_wR_factor_ref         0.1649
_reflns_Friedel_coverage         0.000
_reflns_number_gt                4237
_reflns_number_total             5408
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d5cc00224a2.cif
_cod_data_source_block           mo_20220925c_0m_a
_cod_depositor_comments
'Adding full bibliography for 7134279--7134280.cif.'
_cod_original_cell_volume        1181.8(4)
_cod_database_code               7134280
_shelx_shelxl_version_number     2019/3
_shelx_estimated_absorpt_t_max   0.972
_shelx_estimated_absorpt_t_min   0.969
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All N(H) groups, All N(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups, All O(H) groups
2.a Rotating group:
 N1(H1A,H1B)
2.b Aromatic/amide H refined with riding coordinates:
 N2(H2), C11(H11), C17(H17), C9(H9), C8(H8), C22(H22), C15(H15), C26(H26),
 C1(H1), C18(H18), C5(H5), C25(H25), C20(H20), C19(H19), C24(H24), C2(H2A),
 C23(H23), C3(H3), C4(H4)
2.c Idealised Me refined as rotating group:
 C00W(H00A,H00B,H00C)
2.d Idealised tetrahedral OH refined as rotating group:
 O2(H2B)
;
_shelx_res_checksum              58089
_shelx_hkl_checksum              87460
_olex2_submission_special_instructions 'No special instructions were received'