Electrochemical synthesis of phosphorylated azaspiro[4.5]di/trienones through dearomative spirocyclization.
Zhou, Xiaocong; Wang, Jian; Ma, Dumei; Shen, Yirui; Zhao, Yufen; Wu, Ju; Chemical communications (Cambridge, England) 60 (2024) 7351–7354; doi:10.1039/d4cc02638a

data_7133223
_publ_section_title
;
 Electrochemical synthesis of phosphorylated azaspiro[4.5]di/trienones
 through dearomative spirocyclization.
;
_journal_issue                   57
_journal_name_full               'Chemical communications (Cambridge, England)'
_journal_page_first              7351
_journal_page_last               7354
_journal_paper_doi               10.1039/d4cc02638a
_journal_volume                  60
_journal_year                    2024
_chemical_formula_moiety         'C28 H23 Cl N O3 P, C H Cl3'
_chemical_formula_sum            'C29 H24 Cl4 F N O2 P'
_chemical_formula_weight         610.26
_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
_audit_creation_date             2024-05-27
_audit_creation_method
;
Olex2 1.5
(compiled 2024.02.16 svn.r378c4104 for OlexSys, GUI svn.r6928)
;
_audit_update_record
;
2024-05-27 deposited with the CCDC.	2024-06-18 downloaded from the CCDC.
;
_cell_angle_alpha                81.7500(10)
_cell_angle_beta                 80.1920(10)
_cell_angle_gamma                89.4860(10)
_cell_formula_units_Z            4
_cell_length_a                   10.8350(2)
_cell_length_b                   12.7978(2)
_cell_length_c                   20.7790(4)
_cell_measurement_reflns_used    9787
_cell_measurement_temperature    150.15
_cell_measurement_theta_max      68.47
_cell_measurement_theta_min      3.49
_cell_volume                     2809.45(9)
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2019/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_diffrn_ambient_temperature      150.15
_diffrn_measured_fraction_theta_full 0.994
_diffrn_measured_fraction_theta_max 0.992
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0471
_diffrn_reflns_av_unetI/netI     0.0218
_diffrn_reflns_Laue_measured_fraction_full 0.994
_diffrn_reflns_Laue_measured_fraction_max 0.992
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       25
_diffrn_reflns_limit_l_min       -25
_diffrn_reflns_number            101169
_diffrn_reflns_point_group_measured_fraction_full 0.994
_diffrn_reflns_point_group_measured_fraction_max 0.992
_diffrn_reflns_theta_full        67.679
_diffrn_reflns_theta_max         68.598
_diffrn_reflns_theta_min         2.180
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    4.662
_exptl_absorpt_correction_T_max  0.7531
_exptl_absorpt_correction_T_min  0.6646
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.0788 before and 0.0591 after correction.
The Ratio of minimum to maximum transmission is 0.8825.
The \l/2 correction factor is Not present.
;
_exptl_crystal_colour            'clear light colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.443
_exptl_crystal_description       block
_exptl_crystal_F_000             1252
_exptl_crystal_size_max          0.129
_exptl_crystal_size_mid          0.11
_exptl_crystal_size_min          0.103
_refine_diff_density_max         0.738
_refine_diff_density_min         -0.805
_refine_diff_density_rms         0.054
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.087
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     687
_refine_ls_number_reflns         10279
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.087
_refine_ls_R_factor_all          0.0444
_refine_ls_R_factor_gt           0.0413
_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^)+(0.0438P)^2^+2.7323P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1019
_refine_ls_wR_factor_ref         0.1040
_reflns_Friedel_coverage         0.000
_reflns_number_gt                9365
_reflns_number_total             10279
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d4cc02638a2.cif
_cod_data_source_block           fff
_cod_depositor_comments
'Adding full bibliography for 7133221--7133223.cif.'
_cod_original_cell_volume        2809.46(9)
_cod_database_code               7133223
_shelx_shelxl_version_number     2019/3
_shelx_estimated_absorpt_t_max   0.645
_shelx_estimated_absorpt_t_min   0.585
_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:
 C01U(H01U), C025(H025), C01D(H01D), C02E(H02E), C047(H047), C045(H045)
2.b Aromatic/amide H refined with riding coordinates:
 C015(H015), C01R(H01R), C01W(H01W), C020(H020), C022(H022), C02F(H02F),
 C02H(H02H), C02U(H02U), C02V(H02V), C02Z(H02Z), C038(H038), C039(H039),
 C03A(H03A), C03H(H03H), C03L(H03L), C03P(H03P), C040(H040), C042(H042),
 C01H(H01H), C01J(H01J), C01Z(H01Z), C023(H023), C027(H027), C02A(H02A),
 C02G(H02G), C02M(H02M), C02X(H02X), C030(H030), C031(H031), C032(H032),
 C035(H035), C03I(H03I), C03M(H03M), C03O(H03O), C03Q(H03Q), C03S(H03S)
2.c Idealised Me refined as rotating group:
 C044(H04A,H04B,H04C), C03Y(H03B,H03C,H03D)
;
_shelx_res_checksum              85712
_shelx_hkl_checksum              50580
_olex2_submission_special_instructions 'No special instructions were received'