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_4032202
_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         'C30 H21 Br F N O2'
_chemical_formula_sum            'C30 H21 Br F N O2'
_chemical_formula_weight         526.39
_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             2016-11-16
_audit_creation_method
;
Olex2 1.2-beta
(compiled 2015.01.26 svn.r3150 for OlexSys, GUI svn.r4998)
;
_cell_angle_alpha                93.941(2)
_cell_angle_beta                 107.147(2)
_cell_angle_gamma                108.694(2)
_cell_formula_units_Z            2
_cell_length_a                   9.8413(18)
_cell_length_b                   10.0342(18)
_cell_length_c                   13.628(3)
_cell_measurement_reflns_used    1572
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      22.405
_cell_measurement_theta_min      2.454
_cell_volume                     1198.1(4)
_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 0.981
_diffrn_measured_fraction_theta_max 0.965
_diffrn_measurement_device_type  bruker-CCD
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0254
_diffrn_reflns_av_unetI/netI     0.0666
_diffrn_reflns_Laue_measured_fraction_full 0.981
_diffrn_reflns_Laue_measured_fraction_max 0.965
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            7348
_diffrn_reflns_point_group_measured_fraction_full 0.981
_diffrn_reflns_point_group_measured_fraction_max 0.965
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.386
_diffrn_reflns_theta_min         2.331
_diffrn_source                   'fine-focus sealed tube'
_exptl_absorpt_coefficient_mu    1.752
_exptl_absorpt_correction_T_max  0.8571
_exptl_absorpt_correction_T_min  0.6422
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2008/1 (Bruker,2008) was used for absorption correction.
wR2(int) was 0.0508 before and 0.0341 after correction.
The Ratio of minimum to maximum transmission is 0.7493.
The \l/2 correction factor is 0.0015.
;
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.459
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             536
_exptl_crystal_size_max          0.267
_exptl_crystal_size_mid          0.196
_exptl_crystal_size_min          0.09
_refine_diff_density_max         0.491
_refine_diff_density_min         -0.507
_refine_diff_density_rms         0.112
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.043
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     316
_refine_ls_number_reflns         5254
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      5.290
_refine_ls_R_factor_all          0.0979
_refine_ls_R_factor_gt           0.0508
_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^)+(0.0886P)^2^]
 where P=(Fo^2^+2Fc^2^)/3
;
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1269
_refine_ls_wR_factor_ref         0.1729
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3254
_reflns_number_total             5254
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            jo6b03009_si_003.cif
_cod_data_source_block           8aa
_cod_depositor_comments
'Adding full bibliography for 4032202--4032204.cif.'
_cod_original_cell_volume        1198.2(4)
_cod_database_code               4032202
_shelxl_version_number           2013-2
_shelx_estimated_absorpt_t_max   0.858
_shelx_estimated_absorpt_t_min   0.652
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
2. Restrained distances
 Br1-O1
 3.2 with sigma of 0.01
3.a Ternary CH refined with riding coordinates:
 C2(H2), C3(H3)
3.b Secondary CH2 refined with riding coordinates:
 C24(H24A,H24B)
3.c Aromatic/amide H refined with riding coordinates:
 C11(H11), C17(H17), C14(H14), C27(H27), C23(H23), C26(H26), C22(H22), C8(H8),
 C9(H9), C30(H30), C16(H16), C20(H20), C19(H19), C21(H21), C13(H13), C28(H28),
 C29(H29)
;
_shelx_res_checksum              36857
_shelx_hkl_checksum              40674
_olex2_submission_special_instructions 'No special instructions were received'