Phosphine-catalyzed activation of cyclopropenones: a versatile C<sub>3</sub> synthon for (3+2) annulations with unsaturated electrophiles.
He, Xin; Ma, Pengchen; Tang, Yuhai; Li, Jing; Shen, Shenyu; Lear, Martin J.; Houk, K. N.; Xu, Silong; Chemical science 13 (2022) 12769–12775; doi:10.1039/d2sc04092a

data_1567834
_publ_section_title
;
 Phosphine-catalyzed activation of cyclopropenones: a versatile
 C<sub>3</sub> synthon for (3+2) annulations with unsaturated
 electrophiles.
;
_journal_issue                   43
_journal_name_full               'Chemical science'
_journal_page_first              12769
_journal_page_last               12775
_journal_paper_doi               10.1039/d2sc04092a
_journal_volume                  13
_journal_year                    2022
_chemical_formula_moiety         'C24 H19 N O2'
_chemical_formula_sum            'C24 H19 N O2'
_chemical_formula_weight         353.40
_chemical_name_systematic        hx-523
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2ybc'
_space_group_name_H-M_alt        'P 1 21/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2021-10-11
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_audit_update_record
;
2021-10-29 deposited with the CCDC.	2022-10-14 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 106.730(2)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   9.4143(14)
_cell_length_b                   14.690(2)
_cell_length_c                   13.927(2)
_cell_measurement_reflns_used    5127
_cell_measurement_temperature    296.15
_cell_measurement_theta_max      26.495
_cell_measurement_theta_min      2.259
_cell_volume                     1844.5(5)
_computing_cell_refinement       'SAINT v8.27A (Bruker, 2012)'
_computing_data_reduction        'SAINT v8.27A (Bruker, 2012)'
_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      296.15
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0359
_diffrn_reflns_av_unetI/netI     0.0281
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            18618
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.537
_diffrn_reflns_theta_min         2.062
_exptl_absorpt_coefficient_mu    0.081
_exptl_absorpt_correction_T_max  0.7454
_exptl_absorpt_correction_T_min  0.6679
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2012/1 (Bruker,2012) was used for absorption correction.
wR2(int) was 0.0553 before and 0.0470 after correction.
The Ratio of minimum to maximum transmission is 0.8960.
The \l/2 correction factor is 0.0015.
;
_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    1.273
_exptl_crystal_description       block
_exptl_crystal_F_000             744
_exptl_crystal_size_max          0.26
_exptl_crystal_size_mid          0.24
_exptl_crystal_size_min          0.2
_refine_diff_density_max         0.224
_refine_diff_density_min         -0.214
_refine_diff_density_rms         0.039
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.021
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     246
_refine_ls_number_reflns         3822
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.021
_refine_ls_R_factor_all          0.0568
_refine_ls_R_factor_gt           0.0385
_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^)+(0.0405P)^2^+0.6836P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0906
_refine_ls_wR_factor_ref         0.1002
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2909
_reflns_number_total             3822
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d2sc04092a2.cif
_cod_data_source_block           mo_hexin_20200604_523_0m
_cod_depositor_comments
;
Adding full bibliography for 1567832--1567834.cif.

2025-07-10
Z value and formula fixed to values more according to usual
chemical conventions.                 miguel
;
_cod_original_formula_sum            'C96 H76 N4 O8'
_cod_original_formula_weight         1413.60
_cod_original_formula_moiety         '4(C24 H19 N O2)'
_cod_original_formula_units_Z            1
_cod_original_cell_volume        1844.6(5)
_cod_database_code               1567834
_shelx_shelxl_version_number     2014/7
_shelx_estimated_absorpt_t_max   0.984
_shelx_estimated_absorpt_t_min   0.979
_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 Aromatic/amide H refined with riding coordinates:
 C008(H008), C00C(H00C), C00D(H00D), C00E(H00E), C00F(H00F), C00G(H00G),
 C00H(H00H), C00I(H00I), C00K(H00K), C00L(H00L), C00N(H00N), C00O(H00O),
 C00P(H00P)
2.b Idealised Me refined as rotating group:
 C00Q(H00A,H00B,H00J), C00R(H00M,H00Q,H00R)
;
_shelx_res_checksum              3880
_olex2_submission_original_sample_id HX-523
_olex2_submission_special_instructions 'No special instructions were received'