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_1567832
_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         'C28 H33 N2 O'
_chemical_formula_sum            'C28 H33 N2 O'
_chemical_formula_weight         413.56
_chemical_name_systematic        HX-5181
_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
_atom_sites_solution_primary     dual
_audit_creation_date             2021-10-12
_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                89.884(3)
_cell_angle_beta                 85.258(4)
_cell_angle_gamma                89.848(4)
_cell_formula_units_Z            4
_cell_length_a                   6.2055(17)
_cell_length_b                   11.319(3)
_cell_length_c                   32.886(9)
_cell_measurement_reflns_used    9168
_cell_measurement_temperature    296.15
_cell_measurement_theta_max      26.538
_cell_measurement_theta_min      2.188
_cell_volume                     2302.0(11)
_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 0.615
_diffrn_measured_fraction_theta_max 0.637
_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  0.0446
_diffrn_reflns_av_unetI/netI     0.0751
_diffrn_reflns_Laue_measured_fraction_full 0.615
_diffrn_reflns_Laue_measured_fraction_max 0.637
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       41
_diffrn_reflns_limit_l_min       -41
_diffrn_reflns_number            14200
_diffrn_reflns_point_group_measured_fraction_full 0.615
_diffrn_reflns_point_group_measured_fraction_max 0.637
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.671
_diffrn_reflns_theta_min         1.799
_exptl_absorpt_coefficient_mu    0.072
_exptl_absorpt_correction_T_max  0.7454
_exptl_absorpt_correction_T_min  0.6102
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
'SADABS-2012/1 (Bruker,2012) was used for absorption correction. wR2(int) was 0.1683 before and 0.0827 after correction. The Ratio of minimum to maximum transmission is 0.8186. 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    1.193
_exptl_crystal_description       block
_exptl_crystal_F_000             892
_exptl_crystal_size_max          0.24
_exptl_crystal_size_mid          0.22
_exptl_crystal_size_min          0.2
_refine_diff_density_max         0.193
_refine_diff_density_min         -0.290
_refine_diff_density_rms         0.046
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.066
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     559
_refine_ls_number_reflns         6186
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.066
_refine_ls_R_factor_all          0.0995
_refine_ls_R_factor_gt           0.0728
_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^)+(0.0841P)^2^+1.6459P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1952
_refine_ls_wR_factor_ref         0.2062
_reflns_Friedel_coverage         0.000
_reflns_number_gt                4299
_reflns_number_total             6186
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d2sc04092a2.cif
_cod_data_source_block           mo_lidongqiu_20200603_5181_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            'C112 H132 N8 O4'
_cod_original_formula_weight         1654.25
_cod_original_formula_moiety         '4(C28 H33 N2 O)'
_cod_original_formula_units_Z            1
_cod_database_code               1567832
_shelx_shelxl_version_number     2014/7
_shelx_estimated_absorpt_t_max   0.986
_shelx_estimated_absorpt_t_min   0.983
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All N(H) groups
2.a Ternary CH refined with riding coordinates:
 C00D(H00N), C00F(H00F), C01K(H01L), C01L(H01Z)
2.b Secondary CH2 refined with riding coordinates:
 C007(H00A,H00B), C009(H00L,H00M), C00N(H00C,H00D), C00O(H00Q,H00R), C00Q(H00S,
 H00T), C00V(H00E,H00G), C00W(H00X,H00Y), C00Z(H00H,H00J), C011(H01Q,H01R),
 C014(H01A,H01B), C017(H01C,H01D), C01A(H01S,H01T), C01C(H01U,H01V), C01G(H01Y,
 H), C01H(H01G,H01H), C01J(H01J,H01K), C01M(H01M,H01N), C01N(H01,HA), C01O(H0AA,
 HB), C01P(H01O,H01P)
2.c Aromatic/amide H refined with riding coordinates:
 N005(H005), N006(H006), C00H(H00O), C00I(H00I), C00K(H00K), C00P(H00P),
 C00R(H00V), C00S(H00W), C00U(H00U), C00X(H00Z), C00Y(H00), C013(H013),
 C015(H015), C016(H016), C018(H018), C019(H019), C01B(H01E), C01D(H01F),
 C01E(H01W), C01F(H01X), C01I(H01I), C01Q(H1AA)
;
_shelx_res_checksum              8024
_olex2_submission_original_sample_id hx-5181
_olex2_submission_special_instructions 'No special instructions were received'