Phosphorylated cyclopropanes in the synthesis of α-alkylidene-γ-butyrolactones: total synthesis of (±)-savinin, (±)-gadain and (±)-peperomin E.
Lloyd, Matthew G.; Taylor, Richard J. K.; Unsworth, William P.; Organic & biomolecular chemistry 14 (2016) 8971–8988; doi:10.1039/c6ob01527a

data_7155261
_publ_section_title
;
 Phosphorylated cyclopropanes in the synthesis of
 \a-alkylidene-\g-butyrolactones: total synthesis of (+-)-savinin,
 (+-)-gadain and (+-)-peperomin E.
;
_journal_issue                   38
_journal_name_full               'Organic &amp; biomolecular chemistry'
_journal_page_first              8971
_journal_page_last               8988
_journal_paper_doi               10.1039/c6ob01527a
_journal_volume                  14
_journal_year                    2016
_chemical_formula_moiety         'C15 H19 O5 P'
_chemical_formula_sum            'C15 H19 O5 P'
_chemical_formula_weight         310.27
_chemical_melting_point          353.0(10)
_chemical_name_systematic
'(+-)-diethyl ((1R,5S,6S)-2-oxo-6-phenyl-3-oxabicyclo[3.1.0]hexan-1-yl)phosphonate'
_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'
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 1 21/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_audit_creation_date             2014-05-13
_audit_creation_method
;
Olex2 1.2
(compiled 2014.03.20 svn.r2914 for OlexSys, GUI svn.r4816)
;
_audit_update_record
;
2016-03-13 deposited with the CCDC.
2016-08-10 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 90.0578(13)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   12.11290(15)
_cell_length_b                   10.43581(14)
_cell_length_c                   11.94338(15)
_cell_measurement_reflns_used    6651
_cell_measurement_temperature    110.05(10)
_cell_measurement_theta_max      32.0880
_cell_measurement_theta_min      3.4130
_cell_volume                     1509.74(3)
_computing_cell_refinement
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.33 (release 27-03-2014 CrysAlis171 .NET)
(compiled Mar 27 2014,17:12:48)
;
_computing_data_collection
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.33 (release 27-03-2014 CrysAlis171 .NET)
(compiled Mar 27 2014,17:12:48)
;
_computing_data_reduction
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.33 (release 27-03-2014 CrysAlis171 .NET)
(compiled Mar 27 2014,17:12:48)
;
_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    'ShelXS (Sheldrick, 2008)'
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      110.05(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 16.1450
_diffrn_detector_type            Eos
_diffrn_measured_fraction_theta_full 0.977
_diffrn_measured_fraction_theta_max 0.954
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Single source at offset, Eos'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_UB_11      -0.0074880000
_diffrn_orient_matrix_UB_12      0.0513004000
_diffrn_orient_matrix_UB_13      -0.0382073000
_diffrn_orient_matrix_UB_21      -0.0572668000
_diffrn_orient_matrix_UB_22      0.0009036000
_diffrn_orient_matrix_UB_23      0.0124242000
_diffrn_orient_matrix_UB_31      0.0097598000
_diffrn_orient_matrix_UB_32      0.0445752000
_diffrn_orient_matrix_UB_33      0.0437157000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0209
_diffrn_reflns_av_unetI/netI     0.0210
_diffrn_reflns_Laue_measured_fraction_full 0.977
_diffrn_reflns_Laue_measured_fraction_max 0.954
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_h_min       -17
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            13086
_diffrn_reflns_point_group_measured_fraction_full 0.977
_diffrn_reflns_point_group_measured_fraction_max 0.954
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         30.032
_diffrn_reflns_theta_min         3.089
_diffrn_source                   'SuperNova (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    0.201
_exptl_absorpt_correction_T_max  0.976
_exptl_absorpt_correction_T_min  0.963
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.33 (release 27-03-2014 CrysAlis171 .NET)
(compiled Mar 27 2014,17:12:48)
Numerical absorption correction based on gaussian integration over
            a multifaceted crystal model
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            'clear colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.365
_exptl_crystal_description       irregular
_exptl_crystal_F_000             656
_exptl_crystal_recrystallization_method 'Re-crystallisation from solvent'
_exptl_crystal_size_max          0.2985
_exptl_crystal_size_mid          0.1689
_exptl_crystal_size_min          0.1447
_refine_diff_density_max         0.388
_refine_diff_density_min         -0.339
_refine_diff_density_rms         0.047
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.080
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     197
_refine_ls_number_reflns         4207
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.080
_refine_ls_R_factor_all          0.0368
_refine_ls_R_factor_gt           0.0328
_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^)+(0.0373P)^2^+0.6632P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0859
_refine_ls_wR_factor_ref         0.0886
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3798
_reflns_number_total             4207
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c6ob01527a2.cif
_cod_data_source_block           rjkt1408
_cod_depositor_comments
;
The following automatic conversions were performed:

'_chemical_melting_point' value '352-354' was changed to '353.0(10)'
- the average value was taken and precision was estimated.

Automatic conversion script
Id: cif_fix_values 4268 2015-11-12 08:31:59Z antanas 

 Adding full bibliography for 7155261.cif.

 Adding full bibliography for 7155261.cif.
;
_cod_database_code               7155261
_shelxl_version_number           2013-4
_chemical_oxdiff_formula         'C15 H19 O5 P1'
_chemical_oxdiff_usercomment     'Matthew MGL/04/67-P'
_reflns_odcompleteness_completeness 95.19
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     29.97
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All C(H,H,H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2. Uiso/Uaniso restraints and constraints
Uanis(C15A) = Uanis(C15B)
3. Others
 Sof(H14C)=Sof(H14D)=Sof(C15B)=Sof(H15D)=Sof(H15E)=Sof(H15F)=1-FVAR(1)
 Sof(H14A)=Sof(H14B)=Sof(C15A)=Sof(H15A)=Sof(H15B)=Sof(H15C)=FVAR(1)
4.a Ternary CH refined with riding coordinates:
 C3(H3), C4(H4)
4.b Secondary CH2 refined with riding coordinates:
 C5(H5A,H5B), C12(H12A,H12B), C14(H14A,H14B), C14(H14C,H14D)
4.c Aromatic/amide H refined with riding coordinates:
 C7(H7), C8(H8), C9(H9), C10(H10), C11(H11)
4.d Idealised Me refined as rotating group:
 C13(H13A,H13B,H13C), C15A(H15A,H15B,H15C), C15B(H15D,H15E,H15F)
;
_solvent_exptl_crystal_recrystallization_method 'diethyl ether/chloroform'