Phosphine-catalyzed Michael additions to α-methylene-γ-butyrolactones.
Salin, Alexey V.; Islamov, Daut R.; Organic & biomolecular chemistry 17 (2019) 7293–7299; doi:10.1039/c9ob01401b

data_7156981
_publ_section_title
;
 Phosphine-catalyzed Michael additions to \a-methylene-\g-butyrolactones.
;
_journal_issue                   31
_journal_name_full               'Organic &amp; biomolecular chemistry'
_journal_page_first              7293
_journal_page_last               7299
_journal_paper_doi               10.1039/c9ob01401b
_journal_volume                  17
_journal_year                    2019
_chemical_absolute_configuration ad
_chemical_formula_moiety         'C27 H29 O4 P'
_chemical_formula_sum            'C27 H29 O4 P'
_chemical_formula_weight         448.47
_chemical_name_common
(1R,5R,6S,7S,10S,11S)-11-((diphenylphosphoryl)methyl)-1,10-epoxyguaia-3-ene-6,12-olid
_space_group_crystal_system      orthorhombic
_space_group_IT_number           19
_space_group_name_Hall           'P 2ac 2ab'
_space_group_name_H-M_alt        'P 21 21 21'
_symmetry_space_group_name_Hall  'P 2ac 2ab'
_symmetry_space_group_name_H-M   'P 21 21 21'
_atom_sites_solution_hydrogens   geom
_audit_creation_date             2019-05-07
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_audit_update_record
;
2019-05-07 deposited with the CCDC.    2019-07-10 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   6.0344(2)
_cell_length_b                   31.7014(10)
_cell_length_c                   12.0302(4)
_cell_measurement_reflns_used    5890
_cell_measurement_temperature    100.00(10)
_cell_measurement_theta_max      76.2480
_cell_measurement_theta_min      3.9290
_cell_volume                     2301.36(13)
_computing_cell_refinement       'CrysAlisPro 1.171.40.43a (Rigaku OD, 2019)'
_computing_data_collection       'CrysAlisPro 1.171.40.43a (Rigaku OD, 2019)'
_computing_data_reduction        'CrysAlisPro 1.171.40.43a (Rigaku OD, 2019)'
_computing_molecular_graphics    'MERCURY 4.1 (Macrae, 2006)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL (Sheldrick, 2008)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      100.00(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            HyPix
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.972
_diffrn_measurement_details
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  t~exp~   \w     \q     \k     \f   Frames
  1  \w      2.00  82.00   0.50    0.16    --   47.45-103.00 152.00  160
  2  \w    -80.00 -35.00   0.50    0.62    -- -105.86 103.00-105.00   90
  3  \w   -118.00 -36.00   0.50    0.62    -- -105.86  41.00 161.00  164
  4  \w     81.00 121.00   0.50    0.62    --  105.86  88.00  -0.00   80
  5  \w   -119.00 -93.00   0.50    0.16    --  -47.45-125.00-120.00   52
  6  \w   -119.00 -71.00   0.50    0.16    --  -47.45-125.00 -60.00   96
  7  \w     16.00  95.00   0.50    0.16    --   47.45-125.00  60.00  158
  8  \w     74.00 102.00   0.50    0.16    --   47.45 125.00  30.00   56
  9  \w   -116.00 -89.00   0.50    0.62    -- -105.86  15.00 -60.00   54
 10  \w   -167.00-138.00   0.50    0.62    -- -105.86 -15.00 -90.00   58
 11  \w   -176.00 -92.00   0.50    0.62    -- -105.86 -15.00 -60.00  168
 12  \w   -131.00-105.00   0.50    0.62    -- -105.86 -15.00 -90.00   52
 13  \w     36.00 113.00   0.50    0.62    --  105.86 -45.00 150.00  154
 14  \w     46.00 107.00   0.50    0.62    --  105.86 -94.00   0.00  122
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type
'XtaLAB Synergy, Single source at home/near, HyPix'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.2257367000
_diffrn_orient_matrix_UB_12      0.0225229000
_diffrn_orient_matrix_UB_13      -0.0074627000
_diffrn_orient_matrix_UB_21      -0.0949501000
_diffrn_orient_matrix_UB_22      -0.0376287000
_diffrn_orient_matrix_UB_23      -0.0655259000
_diffrn_orient_matrix_UB_31      -0.0722542000
_diffrn_orient_matrix_UB_32      -0.0209380000
_diffrn_orient_matrix_UB_33      0.1097533000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0513
_diffrn_reflns_av_unetI/netI     0.0507
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.972
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_k_max       30
_diffrn_reflns_limit_k_min       -39
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_number            11464
_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.957
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         76.407
_diffrn_reflns_theta_min         2.788
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'PhotonJet (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    1.311
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.49215
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.40.43a (Rigaku Oxford Diffraction, 2019)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            'clear colourless'
_exptl_crystal_density_diffrn    1.294
_exptl_crystal_description       needle
_exptl_crystal_F_000             952
_exptl_crystal_size_max          0.177
_exptl_crystal_size_mid          0.141
_exptl_crystal_size_min          0.113
_refine_diff_density_max         0.643
_refine_diff_density_min         -0.361
_refine_diff_density_rms         0.078
_refine_ls_abs_structure_details
;
 Flack x determined using 1546 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.01(2)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.087
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     291
_refine_ls_number_reflns         4629
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.087
_refine_ls_R_factor_all          0.0718
_refine_ls_R_factor_gt           0.0576
_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^)+(0.0532P)^2^+4.5142P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1408
_refine_ls_wR_factor_ref         0.1614
_reflns_Friedel_coverage         0.697
_reflns_Friedel_fraction_full    0.995
_reflns_Friedel_fraction_max     0.935
_reflns_number_gt                4152
_reflns_number_total             4629
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c9ob01401b2.cif
_cod_data_source_block           sal9
_cod_depositor_comments
'Adding full bibliography for 7156978--7156981.cif.'
_cod_database_code               7156981
_shelx_shelxl_version_number     2014/7
_chemical_oxdiff_formula         'C27 H29 O4 P1'
_shelx_estimated_absorpt_t_max   0.866
_shelx_estimated_absorpt_t_min   0.801
_diffrn_oxdiff_digest_frames
;
0113fd809c3e535e104f90b65a692f4400000457f39
;
_diffrn_oxdiff_digest_hkl
;
0168adb4842fce16a0d9420149d29574591603
;
_reflns_odcompleteness_completeness 99.84
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Ternary CH refined with riding coordinates:
 C5(H5), C6(H6), C7(H7), C11(H11)
2.b Secondary CH2 refined with riding coordinates:
 C2(H2A,H2B), C8(H8A,H8B), C9(H9A,H9B), C13(H13A,H13B)
2.c Aromatic/amide H refined with riding coordinates:
 C3(H3), C17(H17), C18(H18), C19(H19), C20(H20), C21(H21), C23(H23), C24(H24),
 C25(H25), C26(H26), C27(H27)
2.d Idealised Me refined as rotating group:
 C14(H14A,H14B,H14C), C15(H15A,H15B,H15C)
;
_shelx_res_checksum              3246
_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.751
_oxdiff_exptl_absorpt_empirical_full_min 0.648