Dialkyl Phosphite-Initiated Cyclopropanation of α,β-Unsaturated Ketones Using α-Ketoesters or Isatin Derivatives.
Yin, Deng; Liu, Hui; Lu, Chong-Dao; Xu, Yan-Jun; The Journal of organic chemistry 82 (2017) 3252–3261; doi:10.1021/acs.joc.6b03009

data_4032203
_publ_section_title
;
 Dialkyl Phosphite-Initiated Cyclopropanation of \a,\b-Unsaturated Ketones
 Using \a-Ketoesters or Isatin Derivatives.
;
_journal_issue                   6
_journal_name_full               'The Journal of organic chemistry'
_journal_page_first              3252
_journal_page_last               3261
_journal_paper_doi               10.1021/acs.joc.6b03009
_journal_volume                  82
_journal_year                    2017
_chemical_formula_moiety         'C24 H19 Br O3'
_chemical_formula_sum            'C24 H19 Br O3'
_chemical_formula_weight         435.30
_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_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     iterative
_audit_creation_date             2016-06-21
_audit_creation_method
;
Olex2 1.2-beta
(compiled 2015.01.26 svn.r3150 for OlexSys, GUI svn.r4998)
;
_cell_angle_alpha                83.271(12)
_cell_angle_beta                 82.416(11)
_cell_angle_gamma                72.366(11)
_cell_formula_units_Z            2
_cell_length_a                   6.927(6)
_cell_length_b                   11.029(10)
_cell_length_c                   14.424(13)
_cell_measurement_reflns_used    1217
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      21.183
_cell_measurement_theta_min      2.506
_cell_volume                     1037.5(16)
_computing_cell_refinement       'SAINT v7.68A (Bruker, 2009)'
_computing_data_reduction        'SAINT v7.68A (Bruker, 2009)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2008)'
_computing_structure_solution    'olex2.solve (Bourhis et al., 2015)'
_diffrn_ambient_temperature      296.15
_diffrn_measured_fraction_theta_full 0.983
_diffrn_measured_fraction_theta_max 0.960
_diffrn_measurement_device_type  bruker-CCD
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0253
_diffrn_reflns_av_unetI/netI     0.0687
_diffrn_reflns_Laue_measured_fraction_full 0.983
_diffrn_reflns_Laue_measured_fraction_max 0.960
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            6346
_diffrn_reflns_point_group_measured_fraction_full 0.983
_diffrn_reflns_point_group_measured_fraction_max 0.960
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.430
_diffrn_reflns_theta_min         2.317
_diffrn_source                   'fine-focus sealed tube'
_exptl_absorpt_coefficient_mu    2.002
_exptl_absorpt_correction_T_max  0.7041
_exptl_absorpt_correction_T_min  0.5308
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2008/1 (Bruker,2008) was used for absorption correction.
wR2(int) was 0.0551 before and 0.0326 after correction.
The Ratio of minimum to maximum transmission is 0.7539.
The \l/2 correction factor is 0.0015.
;
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.394
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             444
_exptl_crystal_size_max          0.354
_exptl_crystal_size_mid          0.325
_exptl_crystal_size_min          0.156
_refine_diff_density_max         0.253
_refine_diff_density_min         -0.359
_refine_diff_density_rms         0.054
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.982
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     254
_refine_ls_number_reflns         4538
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.982
_refine_ls_R_factor_all          0.1126
_refine_ls_R_factor_gt           0.0475
_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^)+(0.0638P)^2^+0.0208P]
 where P=(Fo^2^+2Fc^2^)/3
;
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1126
_refine_ls_wR_factor_ref         0.1442
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2325
_reflns_number_total             4538
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            jo6b03009_si_002.cif
_cod_data_source_block           6aa
_cod_depositor_comments
'Adding full bibliography for 4032202--4032204.cif.'
_cod_original_cell_volume        1037.4(17)
_cod_database_code               4032203
_shelxl_version_number           2013-2
_shelx_estimated_absorpt_t_max   0.745
_shelx_estimated_absorpt_t_min   0.538
_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:
 C3(H3), C4(H4)
2.b Aromatic/amide H refined with riding coordinates:
 C20(H20), C19(H19), C17(H17), C13(H13), C9(H9), C7(H7), C10(H10), C15(H15),
 C14(H14), C23(H23), C22(H22), C11(H11), C8(H8), C16(H16)
2.c Idealised Me refined as rotating group:
 C5(H5A,H5B,H5C)
;
_shelx_res_checksum              19863
_shelx_hkl_checksum              34537
_olex2_submission_special_instructions 'No special instructions were received'